S1

Palladium(II) complexes with electron-poor 45-disubstituted diimidazol-2-ylidene ligands synthesis characterization and

catalytic activity

Piermaria Pinterdagger Andrea Biffisdagger Cristina Tubarodagger Mario TenneDagger Maria KalinerDagger Thomas StrassnerDagger

dagger Dipartimento di Scienze Chimiche Universitagrave di Padova via Marzolo 1 35131 Padova Italy E-mail andreabiffisunipdit

Dagger Fachrichtung Chemie und Lebensmittelchemie Technische Universitaumlt Dresden Bergstrasse 66 01069 Dresden Germany

Supporting Information

Additional X-ray crystallographic details pp S2-S4

NMR spectra of the compounds pp S5-S20

Electronic Supplementary Material (ESI) for Dalton TransactionsThis journal is copy The Royal Society of Chemistry 2015

S2

Structure Determination

Preliminary examination and data collection were carried out on a NONIUS κ-CCD diffraction

system equipped with an Oxford Cryosystems cooler at the window of a fine-focus sealed tube

using graphite-monochromated Mo Kα radiation (λ = 071073 Aring)

The reflections were merged and corrected from Lorentz polarization and decay effects An

absorption correction was applied using SADABS1 The structures were solved by a combination of

direct methods23 with the aid of difference Fourier synthesis and were refined against all data using

SHELXL-974 Hydrogen atoms were assigned to calculated positions and then refined using the

SHELXL-97 riding model All non-hydrogen atoms were refined with anisotropic displacement

parameters Full-matrix least-squares refinements were carried out by minimizing Σw(Fo2 minus Fc

2)2

with the SHELXL-97 weighting scheme Details of the structure determinations are given in the

Supporting Information Neutral-atom scattering factors for all atoms and anomalous dispersion

corrections for the non-hydrogen atoms were taken from the International Tables for

Crystallography All calculations were performed with the programs COLLECT5 DIRAX6

EVALCCD7 SIR922 SIR973SHELXLE8SADABS1 the SHELXL-97 package4 and ENCIFER9

Images of the solid state structures were generated with ORTEP-310

References

(1) Sheldrick G M SADABS Version 210 University of Goettingen Goettingen Germany 2002

(2) Altomare A Cascarano G Giacovazzo C Guagliardi A Burla M C Polidori G Camalli M J

Appl Crystallogr1994 27 435

(3) Altomare A Burla M C Camalli M Cascarano G L Giacovazzo C Guagliardi A Moliterni A

G G Polidori G Spagna R J Appl Crystallogr1999 32 115-119

(4) Sheldrick G M Acta Crystallogr Sect A Found Crystallogr2008 A64 112-122

(5) Hooft R W WData Collection Software for Nonius-Kappa CCD Nonius BV Delft The

Netherlands 2001

(6) Duisenberg A J M J Appl Crystallogr1992 25 92-96

(7) Duisenberg A J M Kroon-Batenburg L M J Schreurs A M M J Appl Crystallogr2003 36

220-229

S3

(8) Huebschle C B Sheldrick G M Dittrich B J ApplCrystallogr2011 44 1281-1284

(9) Allen F H Johnson O Shields G P Smith B R Towler M J Appl Crystallogr2004 37 335-

338

(10) Farrugia L J J Appl Crystallogr2012 45 849-854

Table S1 Crystallographic Data for Compounds 3a and 3b

3a 3b

empirical formula C29H27Br6Cl12N13Pd3 C17H26Br2Cl4N6O2Pd formula weight 178170 75446 temperature (K) 198(2) 198(2) wavelength (Aring) 071073 071073 crystal system orthorhombic triclinic space group Pbca P-1 unit cell dimensions (in Aring and deg) a = 19767(5) α = 90 a = 80460(14) α = 72144(9) b = 15478(10) β = 90 b = 11572(2) β= 89760(14) c = 34001(9) γ = 90 c = 157320(13) γ = 74103(15) volume (in Aring3) 10403(8) 13360(4) Z 8 2 density (gcm3 calculated) 2275 1875 absorptioncoeff (mm-1) 6292 4112 F(000) 6752 740 crystal size (mm) 048 x 018 x 017 073 x 053 x 038 θ range for data collection (deg) 206 to 2325 264 to 2640 index ranges -21 lthlt 21 -9lthlt 10 -17ltklt 17 -14ltklt 13 -37ltllt 37 -19ltllt 18 reflections collected 177002 13850 independent reflections 7462[R(int) = 01558] 4963 [R(int) = 00242] absorption correction semi-empirical from equivalents semi-empirical from equivalents refinement method full-matrix least-squares on F2 full-matrix least-squares on F2 datarestraintsparameters 74620575 49630295 goodness of fit on F2 1077 1159 final R indices [Igt2σ(I)] R1 = 00423 wR2 = 01044 R1 = 00341 wR2 = 00746 R indices (all data) R1 = 00849 wR2 = 01297 R1 = 00585 wR2 = 00809 largest diff peak and hole (eA-3) 01134 and -1119 0590 and -0521

S4

Table S2 Crystallographic Data for Compounds 3c and 3e

3c 3e

empirical formula C16H14Br2Cl4N4Pd C15H12Br2N8Pd formula weight 67033 57055 temperature (K) 198(2) 198(2) wavelength (Aring) 071073 071073 crystal system orthorhomic tetragonal space group Pnma I41cd unit cell dimensions (in Aring and deg) a = 13430(3) α = 90 a = 23913(3) α = 90 b = 18758(2) β = 90 b = 23913(3) β = 90 c = 8310(6) γ = 90 c = 13699(3) γ = 90 volume (in Aring3) 20935(16) 78335(16) Z 4 16 density (gcm3 calculated) 2127 1935 absorptioncoeff (mm-1) 5225 5044 F(000) 1288 4384 crystal size (mm) 053 x 036 x 024 025x 022 x 022 θ range for data collection (deg) 217 to 2325 321 to 2520 index ranges -16lthlt 16 -28 lthlt 28 -23ltklt 23 -28 ltklt 28 -10ltllt 10 -16 ltllt 16 reflections collected 43521 72663 independent reflections 2215 [R(int) = 00669] 3514 [R(int) = 00793] absorption correction semi-empirical from equivalents semi-empirical from equivalents refinement method full-matrix least-squares on F2 full-matrix least-squares on F2 datarestraintsparameters 22150125 35141237 goodness of fit on F2 1084 1056 final R indices [Igt2σ(I)] R1 = 00299 wR2 = 00608 R1 = 00331 wR2 = 00736 R indices (all data) R1 = 00472 wR2 = 00659 R1 = 00394 wR2 = 00764 largest diff peak and hole (eA-3) 0621 and -0643 0625 and -0355

S5

1a

1H-NMR (300 MHz DMSO-d6) δ 820 (s 2H) 639 (s 2H) 13C NMR (75 MHz DMSO) δ 1373 (s) 12557 (s) 1122 (s) 538 (s)

S6

1b

1H-NMR (300 MHz DMSO) δ 787 (s 2H) 404 (t J = 72 Hz 4H) 229 (t J = 72 Hz 2H) 13C-NMR (75 MHz DMSO) δ 1360 (s) 1244 (s) 1120 (s) 428 (s) 293 (s)

S7

1c

1H-NMR (300 MHz DMF) δ 797 (s 2H) 739 (dd J = 57 34 Hz 2H) 683 (dd J = 56 34 Hz 2H) 547 (s 4H) 13C-NMR (75 MHz DMSO) δ 1366 (s) 1330(s) 12852 (s) 1268 (s) 1248 (s) 1127 (s) 461 (s)

S8

1d

1H-NMR (300 MHz DMSO) δ 861 (s 2H) 677 (s 2H) 13C-NMR (75 MHz DMSO) δ 1439 (s) 1225 (s) 1127 (s) 1120 (s) 1079 (s) 558 (s)

S9

1e

1H-NMR (300 MHz DMSO) δ 838 (s 2H) 430 (t J = 71 Hz 4H) 248 ndash 233 (m 2H) 13C-NMR (75 MHz DMSO) δ 1433 (s) 1213 (s) 1124(s) 1123(s) 1085 (s) 444 (s) 292 (s)

S10

1f

1H-NMR (300 MHz DMSO) δ 843 (s 2H) 753 (dd J = 57 33 Hz 2H) 722 (dd J = 56 34 Hz 2H) 572 (s 4H) 13C-NMR (75 MHz DMSO) δ 1437 (s) 13223 (s) 1296 (s) 1290 (s) 12220 (s) 1123 (s)1122 (s) 1083 (s) 479 (s)

S11

2a

S12

1H-NMR (300 MHz DMSO) δ 976 (s 2H) 694 (s 2H) 394 (s 6H)

13C- NMR (75 MHz DMSO) δ 1385 (s) 1204 (s) 1190 (s) 558 (s) 355 (s)

19F-NMR (282 MHz DMSO) δ -14896(s) -14901(s)

S13

2b

S14

1H-NMR (500 MHz DMSO) δ 944 (s 2H) 437 (t J = 72 Hz 4H) 386 (s 6H) 242 ndash 229 (m 2H)

13C-NMR (126 MHz DMSO) δ 1365 (s) 1194 (s) 1181 (s) 448 (s) 349 (s) 272 (s)

19F-NMR (282 MHz DMSO) δ -14895(s) -14900(s)

S15

2c

S16

1H-NMR (300 MHz DMSO) δ 931 (s 2H) 753 (dd J = 57 33 Hz 2H) 726 (dd J = 56 34 Hz 2H) 567 (s 4H) 389

(s 6H)

13C-NMR (75 MHz DMSO) δ 1368 (s) 13062 (s) 1297 (s) 1285 (s) 1202 (s) 1185 (s) 484 (s) 352 (s)

19F-NMR (282 MHz DMSO) δ -14891(s) -14897(s)

S17

2e

S18

1H-NMR (300 MHz DMSO) δ 978 (s 2H) 458 (t J = 71 Hz 4H) 411 (s 6H)

13C-NMR (75 MHz DMSO) δ 1425 (s) 1161 (s) 1148 (s) 1060 (s) 472 (s) 372 (s) 277 (s)

19F NMR (282 MHz DMSO) δ -14894(s) -14900(s)

S19

2f

S20

1H-NMR (300 MHz DMSO) δ 965 (s 2H) 768 (dt J = 74 37 Hz 2H) 757 ndash 742 (m 2H) 591 (s 4H) 412 (s 6H)

13C-NMR (75 MHz DMSO) δ 1426 (s) 1307 (s) 1303 (s) 1302 (s) 1171 (s) 1143 (s) 1060 (s) 1059 (s) 505 (s)

372 (s)

19F-NMR (282 MHz DMSO) δ -14897(s) -14903(s)

S21

3a

1H-NMR (600 MHz DMSO) δ 639 (d J = 144 Hz 1H) 604 (d J = 144 Hz 1H) 388 (s 6H)

13C-NMR (151 MHz DMSO) δ 1616 (s) 1172 (s) 1165 (s) 589 (s) 376 (s)

S22

3b

1H-NMR (300 MHz DMSO) δ 495 (dd J = 151 111 Hz 2H) 449 (dd J = 150 58 Hz 2H) 393 (s 6H) 241 (t J = 61

Hz 1H) 188 ndash 165 (m 1H)

13C-NMR (75 MHz DMSO) δ 1170(s) 1164 (s) 549 (s) 501 (s) 368 (s) 285 (s)

S23

3c

1H-NMR (600 MHz DMSO) δ 804 (dd J = 57 35 Hz 2H) 750 (dd J = 57 34 Hz 2H) 665 (d J = 152 Hz 2H) 542

(d J = 153 Hz 2H) 398 (s 6H) 13C-NMR (151 MHz DMSO) δ 1346 (s) 1342 (s) 1184 (s) 1162 (s) 650(s) 516 (s) 374 (s)

S24

3e

1H-NMR (600 MHz DMSO) δ 511 (dd J = 152 115 Hz 2H) 457 (dd J = 150 58 Hz 2H) 413 (s 6H) 228 (dd J =

272 114 Hz 1H)

13C-NMR (151 MHz DMSO) δ 1162 (s) 1155 (s) 1072(s) 1070 (s) 523 (s) 384 (s) 280 (s)

S25

3f

1H-NMR (600 MHz DMSO) δ 795 (dd J = 57 35 Hz 2H) 763 (dd J = 57 34 Hz 2H) 681 (d J = 152 Hz 2H) 571

(d J = 153 Hz 2H) 417 (s 6H)

13C-NMR (151 MHz DMSO) δ 1721 (s) 1343 (s) 1336 (s) 1303 (s) 1181 (s) 1141 (s) 1079 (s) 1069 (s) 528 (s)

S2

Structure Determination

Preliminary examination and data collection were carried out on a NONIUS κ-CCD diffraction

system equipped with an Oxford Cryosystems cooler at the window of a fine-focus sealed tube

using graphite-monochromated Mo Kα radiation (λ = 071073 Aring)

The reflections were merged and corrected from Lorentz polarization and decay effects An

absorption correction was applied using SADABS1 The structures were solved by a combination of

direct methods23 with the aid of difference Fourier synthesis and were refined against all data using

SHELXL-974 Hydrogen atoms were assigned to calculated positions and then refined using the

SHELXL-97 riding model All non-hydrogen atoms were refined with anisotropic displacement

parameters Full-matrix least-squares refinements were carried out by minimizing Σw(Fo2 minus Fc

2)2

with the SHELXL-97 weighting scheme Details of the structure determinations are given in the

Supporting Information Neutral-atom scattering factors for all atoms and anomalous dispersion

corrections for the non-hydrogen atoms were taken from the International Tables for

Crystallography All calculations were performed with the programs COLLECT5 DIRAX6

EVALCCD7 SIR922 SIR973SHELXLE8SADABS1 the SHELXL-97 package4 and ENCIFER9

Images of the solid state structures were generated with ORTEP-310

References

(1) Sheldrick G M SADABS Version 210 University of Goettingen Goettingen Germany 2002

(2) Altomare A Cascarano G Giacovazzo C Guagliardi A Burla M C Polidori G Camalli M J

Appl Crystallogr1994 27 435

(3) Altomare A Burla M C Camalli M Cascarano G L Giacovazzo C Guagliardi A Moliterni A

G G Polidori G Spagna R J Appl Crystallogr1999 32 115-119

(4) Sheldrick G M Acta Crystallogr Sect A Found Crystallogr2008 A64 112-122

(5) Hooft R W WData Collection Software for Nonius-Kappa CCD Nonius BV Delft The

Netherlands 2001

(6) Duisenberg A J M J Appl Crystallogr1992 25 92-96

(7) Duisenberg A J M Kroon-Batenburg L M J Schreurs A M M J Appl Crystallogr2003 36

220-229

S3

(8) Huebschle C B Sheldrick G M Dittrich B J ApplCrystallogr2011 44 1281-1284

(9) Allen F H Johnson O Shields G P Smith B R Towler M J Appl Crystallogr2004 37 335-

338

(10) Farrugia L J J Appl Crystallogr2012 45 849-854

Table S1 Crystallographic Data for Compounds 3a and 3b

3a 3b

empirical formula C29H27Br6Cl12N13Pd3 C17H26Br2Cl4N6O2Pd formula weight 178170 75446 temperature (K) 198(2) 198(2) wavelength (Aring) 071073 071073 crystal system orthorhombic triclinic space group Pbca P-1 unit cell dimensions (in Aring and deg) a = 19767(5) α = 90 a = 80460(14) α = 72144(9) b = 15478(10) β = 90 b = 11572(2) β= 89760(14) c = 34001(9) γ = 90 c = 157320(13) γ = 74103(15) volume (in Aring3) 10403(8) 13360(4) Z 8 2 density (gcm3 calculated) 2275 1875 absorptioncoeff (mm-1) 6292 4112 F(000) 6752 740 crystal size (mm) 048 x 018 x 017 073 x 053 x 038 θ range for data collection (deg) 206 to 2325 264 to 2640 index ranges -21 lthlt 21 -9lthlt 10 -17ltklt 17 -14ltklt 13 -37ltllt 37 -19ltllt 18 reflections collected 177002 13850 independent reflections 7462[R(int) = 01558] 4963 [R(int) = 00242] absorption correction semi-empirical from equivalents semi-empirical from equivalents refinement method full-matrix least-squares on F2 full-matrix least-squares on F2 datarestraintsparameters 74620575 49630295 goodness of fit on F2 1077 1159 final R indices [Igt2σ(I)] R1 = 00423 wR2 = 01044 R1 = 00341 wR2 = 00746 R indices (all data) R1 = 00849 wR2 = 01297 R1 = 00585 wR2 = 00809 largest diff peak and hole (eA-3) 01134 and -1119 0590 and -0521

S4

Table S2 Crystallographic Data for Compounds 3c and 3e

3c 3e

empirical formula C16H14Br2Cl4N4Pd C15H12Br2N8Pd formula weight 67033 57055 temperature (K) 198(2) 198(2) wavelength (Aring) 071073 071073 crystal system orthorhomic tetragonal space group Pnma I41cd unit cell dimensions (in Aring and deg) a = 13430(3) α = 90 a = 23913(3) α = 90 b = 18758(2) β = 90 b = 23913(3) β = 90 c = 8310(6) γ = 90 c = 13699(3) γ = 90 volume (in Aring3) 20935(16) 78335(16) Z 4 16 density (gcm3 calculated) 2127 1935 absorptioncoeff (mm-1) 5225 5044 F(000) 1288 4384 crystal size (mm) 053 x 036 x 024 025x 022 x 022 θ range for data collection (deg) 217 to 2325 321 to 2520 index ranges -16lthlt 16 -28 lthlt 28 -23ltklt 23 -28 ltklt 28 -10ltllt 10 -16 ltllt 16 reflections collected 43521 72663 independent reflections 2215 [R(int) = 00669] 3514 [R(int) = 00793] absorption correction semi-empirical from equivalents semi-empirical from equivalents refinement method full-matrix least-squares on F2 full-matrix least-squares on F2 datarestraintsparameters 22150125 35141237 goodness of fit on F2 1084 1056 final R indices [Igt2σ(I)] R1 = 00299 wR2 = 00608 R1 = 00331 wR2 = 00736 R indices (all data) R1 = 00472 wR2 = 00659 R1 = 00394 wR2 = 00764 largest diff peak and hole (eA-3) 0621 and -0643 0625 and -0355

S5

1a

1H-NMR (300 MHz DMSO-d6) δ 820 (s 2H) 639 (s 2H) 13C NMR (75 MHz DMSO) δ 1373 (s) 12557 (s) 1122 (s) 538 (s)

S6

1b

1H-NMR (300 MHz DMSO) δ 787 (s 2H) 404 (t J = 72 Hz 4H) 229 (t J = 72 Hz 2H) 13C-NMR (75 MHz DMSO) δ 1360 (s) 1244 (s) 1120 (s) 428 (s) 293 (s)

S7

1c

1H-NMR (300 MHz DMF) δ 797 (s 2H) 739 (dd J = 57 34 Hz 2H) 683 (dd J = 56 34 Hz 2H) 547 (s 4H) 13C-NMR (75 MHz DMSO) δ 1366 (s) 1330(s) 12852 (s) 1268 (s) 1248 (s) 1127 (s) 461 (s)

S8

1d

1H-NMR (300 MHz DMSO) δ 861 (s 2H) 677 (s 2H) 13C-NMR (75 MHz DMSO) δ 1439 (s) 1225 (s) 1127 (s) 1120 (s) 1079 (s) 558 (s)

S9

1e

1H-NMR (300 MHz DMSO) δ 838 (s 2H) 430 (t J = 71 Hz 4H) 248 ndash 233 (m 2H) 13C-NMR (75 MHz DMSO) δ 1433 (s) 1213 (s) 1124(s) 1123(s) 1085 (s) 444 (s) 292 (s)

S10

1f

1H-NMR (300 MHz DMSO) δ 843 (s 2H) 753 (dd J = 57 33 Hz 2H) 722 (dd J = 56 34 Hz 2H) 572 (s 4H) 13C-NMR (75 MHz DMSO) δ 1437 (s) 13223 (s) 1296 (s) 1290 (s) 12220 (s) 1123 (s)1122 (s) 1083 (s) 479 (s)

S11

2a

S12

1H-NMR (300 MHz DMSO) δ 976 (s 2H) 694 (s 2H) 394 (s 6H)

13C- NMR (75 MHz DMSO) δ 1385 (s) 1204 (s) 1190 (s) 558 (s) 355 (s)

19F-NMR (282 MHz DMSO) δ -14896(s) -14901(s)

S13

2b

S14

1H-NMR (500 MHz DMSO) δ 944 (s 2H) 437 (t J = 72 Hz 4H) 386 (s 6H) 242 ndash 229 (m 2H)

13C-NMR (126 MHz DMSO) δ 1365 (s) 1194 (s) 1181 (s) 448 (s) 349 (s) 272 (s)

19F-NMR (282 MHz DMSO) δ -14895(s) -14900(s)

S15

2c

S16

1H-NMR (300 MHz DMSO) δ 931 (s 2H) 753 (dd J = 57 33 Hz 2H) 726 (dd J = 56 34 Hz 2H) 567 (s 4H) 389

(s 6H)

13C-NMR (75 MHz DMSO) δ 1368 (s) 13062 (s) 1297 (s) 1285 (s) 1202 (s) 1185 (s) 484 (s) 352 (s)

19F-NMR (282 MHz DMSO) δ -14891(s) -14897(s)

S17

2e

S18

1H-NMR (300 MHz DMSO) δ 978 (s 2H) 458 (t J = 71 Hz 4H) 411 (s 6H)

13C-NMR (75 MHz DMSO) δ 1425 (s) 1161 (s) 1148 (s) 1060 (s) 472 (s) 372 (s) 277 (s)

19F NMR (282 MHz DMSO) δ -14894(s) -14900(s)

S19

2f

S20

1H-NMR (300 MHz DMSO) δ 965 (s 2H) 768 (dt J = 74 37 Hz 2H) 757 ndash 742 (m 2H) 591 (s 4H) 412 (s 6H)

13C-NMR (75 MHz DMSO) δ 1426 (s) 1307 (s) 1303 (s) 1302 (s) 1171 (s) 1143 (s) 1060 (s) 1059 (s) 505 (s)

372 (s)

19F-NMR (282 MHz DMSO) δ -14897(s) -14903(s)

S21

3a

1H-NMR (600 MHz DMSO) δ 639 (d J = 144 Hz 1H) 604 (d J = 144 Hz 1H) 388 (s 6H)

13C-NMR (151 MHz DMSO) δ 1616 (s) 1172 (s) 1165 (s) 589 (s) 376 (s)

S22

3b

1H-NMR (300 MHz DMSO) δ 495 (dd J = 151 111 Hz 2H) 449 (dd J = 150 58 Hz 2H) 393 (s 6H) 241 (t J = 61

Hz 1H) 188 ndash 165 (m 1H)

13C-NMR (75 MHz DMSO) δ 1170(s) 1164 (s) 549 (s) 501 (s) 368 (s) 285 (s)

S23

3c

1H-NMR (600 MHz DMSO) δ 804 (dd J = 57 35 Hz 2H) 750 (dd J = 57 34 Hz 2H) 665 (d J = 152 Hz 2H) 542

(d J = 153 Hz 2H) 398 (s 6H) 13C-NMR (151 MHz DMSO) δ 1346 (s) 1342 (s) 1184 (s) 1162 (s) 650(s) 516 (s) 374 (s)

S24

3e

1H-NMR (600 MHz DMSO) δ 511 (dd J = 152 115 Hz 2H) 457 (dd J = 150 58 Hz 2H) 413 (s 6H) 228 (dd J =

272 114 Hz 1H)

13C-NMR (151 MHz DMSO) δ 1162 (s) 1155 (s) 1072(s) 1070 (s) 523 (s) 384 (s) 280 (s)

S25

3f

1H-NMR (600 MHz DMSO) δ 795 (dd J = 57 35 Hz 2H) 763 (dd J = 57 34 Hz 2H) 681 (d J = 152 Hz 2H) 571

(d J = 153 Hz 2H) 417 (s 6H)

13C-NMR (151 MHz DMSO) δ 1721 (s) 1343 (s) 1336 (s) 1303 (s) 1181 (s) 1141 (s) 1079 (s) 1069 (s) 528 (s)

S3

(8) Huebschle C B Sheldrick G M Dittrich B J ApplCrystallogr2011 44 1281-1284

(9) Allen F H Johnson O Shields G P Smith B R Towler M J Appl Crystallogr2004 37 335-

338

(10) Farrugia L J J Appl Crystallogr2012 45 849-854

Table S1 Crystallographic Data for Compounds 3a and 3b

3a 3b

empirical formula C29H27Br6Cl12N13Pd3 C17H26Br2Cl4N6O2Pd formula weight 178170 75446 temperature (K) 198(2) 198(2) wavelength (Aring) 071073 071073 crystal system orthorhombic triclinic space group Pbca P-1 unit cell dimensions (in Aring and deg) a = 19767(5) α = 90 a = 80460(14) α = 72144(9) b = 15478(10) β = 90 b = 11572(2) β= 89760(14) c = 34001(9) γ = 90 c = 157320(13) γ = 74103(15) volume (in Aring3) 10403(8) 13360(4) Z 8 2 density (gcm3 calculated) 2275 1875 absorptioncoeff (mm-1) 6292 4112 F(000) 6752 740 crystal size (mm) 048 x 018 x 017 073 x 053 x 038 θ range for data collection (deg) 206 to 2325 264 to 2640 index ranges -21 lthlt 21 -9lthlt 10 -17ltklt 17 -14ltklt 13 -37ltllt 37 -19ltllt 18 reflections collected 177002 13850 independent reflections 7462[R(int) = 01558] 4963 [R(int) = 00242] absorption correction semi-empirical from equivalents semi-empirical from equivalents refinement method full-matrix least-squares on F2 full-matrix least-squares on F2 datarestraintsparameters 74620575 49630295 goodness of fit on F2 1077 1159 final R indices [Igt2σ(I)] R1 = 00423 wR2 = 01044 R1 = 00341 wR2 = 00746 R indices (all data) R1 = 00849 wR2 = 01297 R1 = 00585 wR2 = 00809 largest diff peak and hole (eA-3) 01134 and -1119 0590 and -0521

S4

Table S2 Crystallographic Data for Compounds 3c and 3e

3c 3e

empirical formula C16H14Br2Cl4N4Pd C15H12Br2N8Pd formula weight 67033 57055 temperature (K) 198(2) 198(2) wavelength (Aring) 071073 071073 crystal system orthorhomic tetragonal space group Pnma I41cd unit cell dimensions (in Aring and deg) a = 13430(3) α = 90 a = 23913(3) α = 90 b = 18758(2) β = 90 b = 23913(3) β = 90 c = 8310(6) γ = 90 c = 13699(3) γ = 90 volume (in Aring3) 20935(16) 78335(16) Z 4 16 density (gcm3 calculated) 2127 1935 absorptioncoeff (mm-1) 5225 5044 F(000) 1288 4384 crystal size (mm) 053 x 036 x 024 025x 022 x 022 θ range for data collection (deg) 217 to 2325 321 to 2520 index ranges -16lthlt 16 -28 lthlt 28 -23ltklt 23 -28 ltklt 28 -10ltllt 10 -16 ltllt 16 reflections collected 43521 72663 independent reflections 2215 [R(int) = 00669] 3514 [R(int) = 00793] absorption correction semi-empirical from equivalents semi-empirical from equivalents refinement method full-matrix least-squares on F2 full-matrix least-squares on F2 datarestraintsparameters 22150125 35141237 goodness of fit on F2 1084 1056 final R indices [Igt2σ(I)] R1 = 00299 wR2 = 00608 R1 = 00331 wR2 = 00736 R indices (all data) R1 = 00472 wR2 = 00659 R1 = 00394 wR2 = 00764 largest diff peak and hole (eA-3) 0621 and -0643 0625 and -0355

S5

1a

1H-NMR (300 MHz DMSO-d6) δ 820 (s 2H) 639 (s 2H) 13C NMR (75 MHz DMSO) δ 1373 (s) 12557 (s) 1122 (s) 538 (s)

S6

1b

1H-NMR (300 MHz DMSO) δ 787 (s 2H) 404 (t J = 72 Hz 4H) 229 (t J = 72 Hz 2H) 13C-NMR (75 MHz DMSO) δ 1360 (s) 1244 (s) 1120 (s) 428 (s) 293 (s)

S7

1c

1H-NMR (300 MHz DMF) δ 797 (s 2H) 739 (dd J = 57 34 Hz 2H) 683 (dd J = 56 34 Hz 2H) 547 (s 4H) 13C-NMR (75 MHz DMSO) δ 1366 (s) 1330(s) 12852 (s) 1268 (s) 1248 (s) 1127 (s) 461 (s)

S8

1d

1H-NMR (300 MHz DMSO) δ 861 (s 2H) 677 (s 2H) 13C-NMR (75 MHz DMSO) δ 1439 (s) 1225 (s) 1127 (s) 1120 (s) 1079 (s) 558 (s)

S9

1e

1H-NMR (300 MHz DMSO) δ 838 (s 2H) 430 (t J = 71 Hz 4H) 248 ndash 233 (m 2H) 13C-NMR (75 MHz DMSO) δ 1433 (s) 1213 (s) 1124(s) 1123(s) 1085 (s) 444 (s) 292 (s)

S10

1f

1H-NMR (300 MHz DMSO) δ 843 (s 2H) 753 (dd J = 57 33 Hz 2H) 722 (dd J = 56 34 Hz 2H) 572 (s 4H) 13C-NMR (75 MHz DMSO) δ 1437 (s) 13223 (s) 1296 (s) 1290 (s) 12220 (s) 1123 (s)1122 (s) 1083 (s) 479 (s)

S11

2a

S12

1H-NMR (300 MHz DMSO) δ 976 (s 2H) 694 (s 2H) 394 (s 6H)

13C- NMR (75 MHz DMSO) δ 1385 (s) 1204 (s) 1190 (s) 558 (s) 355 (s)

19F-NMR (282 MHz DMSO) δ -14896(s) -14901(s)

S13

2b

S14

1H-NMR (500 MHz DMSO) δ 944 (s 2H) 437 (t J = 72 Hz 4H) 386 (s 6H) 242 ndash 229 (m 2H)

13C-NMR (126 MHz DMSO) δ 1365 (s) 1194 (s) 1181 (s) 448 (s) 349 (s) 272 (s)

19F-NMR (282 MHz DMSO) δ -14895(s) -14900(s)

S15

2c

S16

1H-NMR (300 MHz DMSO) δ 931 (s 2H) 753 (dd J = 57 33 Hz 2H) 726 (dd J = 56 34 Hz 2H) 567 (s 4H) 389

(s 6H)

13C-NMR (75 MHz DMSO) δ 1368 (s) 13062 (s) 1297 (s) 1285 (s) 1202 (s) 1185 (s) 484 (s) 352 (s)

19F-NMR (282 MHz DMSO) δ -14891(s) -14897(s)

S17

2e

S18

1H-NMR (300 MHz DMSO) δ 978 (s 2H) 458 (t J = 71 Hz 4H) 411 (s 6H)

13C-NMR (75 MHz DMSO) δ 1425 (s) 1161 (s) 1148 (s) 1060 (s) 472 (s) 372 (s) 277 (s)

19F NMR (282 MHz DMSO) δ -14894(s) -14900(s)

S19

2f

S20

1H-NMR (300 MHz DMSO) δ 965 (s 2H) 768 (dt J = 74 37 Hz 2H) 757 ndash 742 (m 2H) 591 (s 4H) 412 (s 6H)

13C-NMR (75 MHz DMSO) δ 1426 (s) 1307 (s) 1303 (s) 1302 (s) 1171 (s) 1143 (s) 1060 (s) 1059 (s) 505 (s)

372 (s)

19F-NMR (282 MHz DMSO) δ -14897(s) -14903(s)

S21

3a

1H-NMR (600 MHz DMSO) δ 639 (d J = 144 Hz 1H) 604 (d J = 144 Hz 1H) 388 (s 6H)

13C-NMR (151 MHz DMSO) δ 1616 (s) 1172 (s) 1165 (s) 589 (s) 376 (s)

S22

3b

1H-NMR (300 MHz DMSO) δ 495 (dd J = 151 111 Hz 2H) 449 (dd J = 150 58 Hz 2H) 393 (s 6H) 241 (t J = 61

Hz 1H) 188 ndash 165 (m 1H)

13C-NMR (75 MHz DMSO) δ 1170(s) 1164 (s) 549 (s) 501 (s) 368 (s) 285 (s)

S23

3c

1H-NMR (600 MHz DMSO) δ 804 (dd J = 57 35 Hz 2H) 750 (dd J = 57 34 Hz 2H) 665 (d J = 152 Hz 2H) 542

(d J = 153 Hz 2H) 398 (s 6H) 13C-NMR (151 MHz DMSO) δ 1346 (s) 1342 (s) 1184 (s) 1162 (s) 650(s) 516 (s) 374 (s)

S24

3e

1H-NMR (600 MHz DMSO) δ 511 (dd J = 152 115 Hz 2H) 457 (dd J = 150 58 Hz 2H) 413 (s 6H) 228 (dd J =

272 114 Hz 1H)

13C-NMR (151 MHz DMSO) δ 1162 (s) 1155 (s) 1072(s) 1070 (s) 523 (s) 384 (s) 280 (s)

S25

3f

1H-NMR (600 MHz DMSO) δ 795 (dd J = 57 35 Hz 2H) 763 (dd J = 57 34 Hz 2H) 681 (d J = 152 Hz 2H) 571

(d J = 153 Hz 2H) 417 (s 6H)

13C-NMR (151 MHz DMSO) δ 1721 (s) 1343 (s) 1336 (s) 1303 (s) 1181 (s) 1141 (s) 1079 (s) 1069 (s) 528 (s)

S4

Table S2 Crystallographic Data for Compounds 3c and 3e

3c 3e

empirical formula C16H14Br2Cl4N4Pd C15H12Br2N8Pd formula weight 67033 57055 temperature (K) 198(2) 198(2) wavelength (Aring) 071073 071073 crystal system orthorhomic tetragonal space group Pnma I41cd unit cell dimensions (in Aring and deg) a = 13430(3) α = 90 a = 23913(3) α = 90 b = 18758(2) β = 90 b = 23913(3) β = 90 c = 8310(6) γ = 90 c = 13699(3) γ = 90 volume (in Aring3) 20935(16) 78335(16) Z 4 16 density (gcm3 calculated) 2127 1935 absorptioncoeff (mm-1) 5225 5044 F(000) 1288 4384 crystal size (mm) 053 x 036 x 024 025x 022 x 022 θ range for data collection (deg) 217 to 2325 321 to 2520 index ranges -16lthlt 16 -28 lthlt 28 -23ltklt 23 -28 ltklt 28 -10ltllt 10 -16 ltllt 16 reflections collected 43521 72663 independent reflections 2215 [R(int) = 00669] 3514 [R(int) = 00793] absorption correction semi-empirical from equivalents semi-empirical from equivalents refinement method full-matrix least-squares on F2 full-matrix least-squares on F2 datarestraintsparameters 22150125 35141237 goodness of fit on F2 1084 1056 final R indices [Igt2σ(I)] R1 = 00299 wR2 = 00608 R1 = 00331 wR2 = 00736 R indices (all data) R1 = 00472 wR2 = 00659 R1 = 00394 wR2 = 00764 largest diff peak and hole (eA-3) 0621 and -0643 0625 and -0355

S5

1a

1H-NMR (300 MHz DMSO-d6) δ 820 (s 2H) 639 (s 2H) 13C NMR (75 MHz DMSO) δ 1373 (s) 12557 (s) 1122 (s) 538 (s)

S6

1b

1H-NMR (300 MHz DMSO) δ 787 (s 2H) 404 (t J = 72 Hz 4H) 229 (t J = 72 Hz 2H) 13C-NMR (75 MHz DMSO) δ 1360 (s) 1244 (s) 1120 (s) 428 (s) 293 (s)

S7

1c

1H-NMR (300 MHz DMF) δ 797 (s 2H) 739 (dd J = 57 34 Hz 2H) 683 (dd J = 56 34 Hz 2H) 547 (s 4H) 13C-NMR (75 MHz DMSO) δ 1366 (s) 1330(s) 12852 (s) 1268 (s) 1248 (s) 1127 (s) 461 (s)

S8

1d

1H-NMR (300 MHz DMSO) δ 861 (s 2H) 677 (s 2H) 13C-NMR (75 MHz DMSO) δ 1439 (s) 1225 (s) 1127 (s) 1120 (s) 1079 (s) 558 (s)

S9

1e

1H-NMR (300 MHz DMSO) δ 838 (s 2H) 430 (t J = 71 Hz 4H) 248 ndash 233 (m 2H) 13C-NMR (75 MHz DMSO) δ 1433 (s) 1213 (s) 1124(s) 1123(s) 1085 (s) 444 (s) 292 (s)

S10

1f

1H-NMR (300 MHz DMSO) δ 843 (s 2H) 753 (dd J = 57 33 Hz 2H) 722 (dd J = 56 34 Hz 2H) 572 (s 4H) 13C-NMR (75 MHz DMSO) δ 1437 (s) 13223 (s) 1296 (s) 1290 (s) 12220 (s) 1123 (s)1122 (s) 1083 (s) 479 (s)

S11

2a

S12

1H-NMR (300 MHz DMSO) δ 976 (s 2H) 694 (s 2H) 394 (s 6H)

13C- NMR (75 MHz DMSO) δ 1385 (s) 1204 (s) 1190 (s) 558 (s) 355 (s)

19F-NMR (282 MHz DMSO) δ -14896(s) -14901(s)

S13

2b

S14

1H-NMR (500 MHz DMSO) δ 944 (s 2H) 437 (t J = 72 Hz 4H) 386 (s 6H) 242 ndash 229 (m 2H)

13C-NMR (126 MHz DMSO) δ 1365 (s) 1194 (s) 1181 (s) 448 (s) 349 (s) 272 (s)

19F-NMR (282 MHz DMSO) δ -14895(s) -14900(s)

S15

2c

S16

1H-NMR (300 MHz DMSO) δ 931 (s 2H) 753 (dd J = 57 33 Hz 2H) 726 (dd J = 56 34 Hz 2H) 567 (s 4H) 389

(s 6H)

13C-NMR (75 MHz DMSO) δ 1368 (s) 13062 (s) 1297 (s) 1285 (s) 1202 (s) 1185 (s) 484 (s) 352 (s)

19F-NMR (282 MHz DMSO) δ -14891(s) -14897(s)

S17

2e

S18

1H-NMR (300 MHz DMSO) δ 978 (s 2H) 458 (t J = 71 Hz 4H) 411 (s 6H)

13C-NMR (75 MHz DMSO) δ 1425 (s) 1161 (s) 1148 (s) 1060 (s) 472 (s) 372 (s) 277 (s)

19F NMR (282 MHz DMSO) δ -14894(s) -14900(s)

S19

2f

S20

1H-NMR (300 MHz DMSO) δ 965 (s 2H) 768 (dt J = 74 37 Hz 2H) 757 ndash 742 (m 2H) 591 (s 4H) 412 (s 6H)

13C-NMR (75 MHz DMSO) δ 1426 (s) 1307 (s) 1303 (s) 1302 (s) 1171 (s) 1143 (s) 1060 (s) 1059 (s) 505 (s)

372 (s)

19F-NMR (282 MHz DMSO) δ -14897(s) -14903(s)

S21

3a

1H-NMR (600 MHz DMSO) δ 639 (d J = 144 Hz 1H) 604 (d J = 144 Hz 1H) 388 (s 6H)

13C-NMR (151 MHz DMSO) δ 1616 (s) 1172 (s) 1165 (s) 589 (s) 376 (s)

S22

3b

1H-NMR (300 MHz DMSO) δ 495 (dd J = 151 111 Hz 2H) 449 (dd J = 150 58 Hz 2H) 393 (s 6H) 241 (t J = 61

Hz 1H) 188 ndash 165 (m 1H)

13C-NMR (75 MHz DMSO) δ 1170(s) 1164 (s) 549 (s) 501 (s) 368 (s) 285 (s)

S23

3c

1H-NMR (600 MHz DMSO) δ 804 (dd J = 57 35 Hz 2H) 750 (dd J = 57 34 Hz 2H) 665 (d J = 152 Hz 2H) 542

(d J = 153 Hz 2H) 398 (s 6H) 13C-NMR (151 MHz DMSO) δ 1346 (s) 1342 (s) 1184 (s) 1162 (s) 650(s) 516 (s) 374 (s)

S24

3e

1H-NMR (600 MHz DMSO) δ 511 (dd J = 152 115 Hz 2H) 457 (dd J = 150 58 Hz 2H) 413 (s 6H) 228 (dd J =

272 114 Hz 1H)

13C-NMR (151 MHz DMSO) δ 1162 (s) 1155 (s) 1072(s) 1070 (s) 523 (s) 384 (s) 280 (s)

S25

3f

1H-NMR (600 MHz DMSO) δ 795 (dd J = 57 35 Hz 2H) 763 (dd J = 57 34 Hz 2H) 681 (d J = 152 Hz 2H) 571

(d J = 153 Hz 2H) 417 (s 6H)

13C-NMR (151 MHz DMSO) δ 1721 (s) 1343 (s) 1336 (s) 1303 (s) 1181 (s) 1141 (s) 1079 (s) 1069 (s) 528 (s)

S5

1a

1H-NMR (300 MHz DMSO-d6) δ 820 (s 2H) 639 (s 2H) 13C NMR (75 MHz DMSO) δ 1373 (s) 12557 (s) 1122 (s) 538 (s)

S6

1b

1H-NMR (300 MHz DMSO) δ 787 (s 2H) 404 (t J = 72 Hz 4H) 229 (t J = 72 Hz 2H) 13C-NMR (75 MHz DMSO) δ 1360 (s) 1244 (s) 1120 (s) 428 (s) 293 (s)

S7

1c

1H-NMR (300 MHz DMF) δ 797 (s 2H) 739 (dd J = 57 34 Hz 2H) 683 (dd J = 56 34 Hz 2H) 547 (s 4H) 13C-NMR (75 MHz DMSO) δ 1366 (s) 1330(s) 12852 (s) 1268 (s) 1248 (s) 1127 (s) 461 (s)

S8

1d

1H-NMR (300 MHz DMSO) δ 861 (s 2H) 677 (s 2H) 13C-NMR (75 MHz DMSO) δ 1439 (s) 1225 (s) 1127 (s) 1120 (s) 1079 (s) 558 (s)

S9

1e

1H-NMR (300 MHz DMSO) δ 838 (s 2H) 430 (t J = 71 Hz 4H) 248 ndash 233 (m 2H) 13C-NMR (75 MHz DMSO) δ 1433 (s) 1213 (s) 1124(s) 1123(s) 1085 (s) 444 (s) 292 (s)

S10

1f

1H-NMR (300 MHz DMSO) δ 843 (s 2H) 753 (dd J = 57 33 Hz 2H) 722 (dd J = 56 34 Hz 2H) 572 (s 4H) 13C-NMR (75 MHz DMSO) δ 1437 (s) 13223 (s) 1296 (s) 1290 (s) 12220 (s) 1123 (s)1122 (s) 1083 (s) 479 (s)

S11

2a

S12

1H-NMR (300 MHz DMSO) δ 976 (s 2H) 694 (s 2H) 394 (s 6H)

13C- NMR (75 MHz DMSO) δ 1385 (s) 1204 (s) 1190 (s) 558 (s) 355 (s)

19F-NMR (282 MHz DMSO) δ -14896(s) -14901(s)

S13

2b

S14

1H-NMR (500 MHz DMSO) δ 944 (s 2H) 437 (t J = 72 Hz 4H) 386 (s 6H) 242 ndash 229 (m 2H)

13C-NMR (126 MHz DMSO) δ 1365 (s) 1194 (s) 1181 (s) 448 (s) 349 (s) 272 (s)

19F-NMR (282 MHz DMSO) δ -14895(s) -14900(s)

S15

2c

S16

1H-NMR (300 MHz DMSO) δ 931 (s 2H) 753 (dd J = 57 33 Hz 2H) 726 (dd J = 56 34 Hz 2H) 567 (s 4H) 389

(s 6H)

13C-NMR (75 MHz DMSO) δ 1368 (s) 13062 (s) 1297 (s) 1285 (s) 1202 (s) 1185 (s) 484 (s) 352 (s)

19F-NMR (282 MHz DMSO) δ -14891(s) -14897(s)

S17

2e

S18

1H-NMR (300 MHz DMSO) δ 978 (s 2H) 458 (t J = 71 Hz 4H) 411 (s 6H)

13C-NMR (75 MHz DMSO) δ 1425 (s) 1161 (s) 1148 (s) 1060 (s) 472 (s) 372 (s) 277 (s)

19F NMR (282 MHz DMSO) δ -14894(s) -14900(s)

S19

2f

S20

1H-NMR (300 MHz DMSO) δ 965 (s 2H) 768 (dt J = 74 37 Hz 2H) 757 ndash 742 (m 2H) 591 (s 4H) 412 (s 6H)

13C-NMR (75 MHz DMSO) δ 1426 (s) 1307 (s) 1303 (s) 1302 (s) 1171 (s) 1143 (s) 1060 (s) 1059 (s) 505 (s)

372 (s)

19F-NMR (282 MHz DMSO) δ -14897(s) -14903(s)

S21

3a

1H-NMR (600 MHz DMSO) δ 639 (d J = 144 Hz 1H) 604 (d J = 144 Hz 1H) 388 (s 6H)

13C-NMR (151 MHz DMSO) δ 1616 (s) 1172 (s) 1165 (s) 589 (s) 376 (s)

S22

3b

1H-NMR (300 MHz DMSO) δ 495 (dd J = 151 111 Hz 2H) 449 (dd J = 150 58 Hz 2H) 393 (s 6H) 241 (t J = 61

Hz 1H) 188 ndash 165 (m 1H)

13C-NMR (75 MHz DMSO) δ 1170(s) 1164 (s) 549 (s) 501 (s) 368 (s) 285 (s)

S23

3c

1H-NMR (600 MHz DMSO) δ 804 (dd J = 57 35 Hz 2H) 750 (dd J = 57 34 Hz 2H) 665 (d J = 152 Hz 2H) 542

(d J = 153 Hz 2H) 398 (s 6H) 13C-NMR (151 MHz DMSO) δ 1346 (s) 1342 (s) 1184 (s) 1162 (s) 650(s) 516 (s) 374 (s)

S24

3e

1H-NMR (600 MHz DMSO) δ 511 (dd J = 152 115 Hz 2H) 457 (dd J = 150 58 Hz 2H) 413 (s 6H) 228 (dd J =

272 114 Hz 1H)

13C-NMR (151 MHz DMSO) δ 1162 (s) 1155 (s) 1072(s) 1070 (s) 523 (s) 384 (s) 280 (s)

S25

3f

1H-NMR (600 MHz DMSO) δ 795 (dd J = 57 35 Hz 2H) 763 (dd J = 57 34 Hz 2H) 681 (d J = 152 Hz 2H) 571

(d J = 153 Hz 2H) 417 (s 6H)

13C-NMR (151 MHz DMSO) δ 1721 (s) 1343 (s) 1336 (s) 1303 (s) 1181 (s) 1141 (s) 1079 (s) 1069 (s) 528 (s)

S6

1b

1H-NMR (300 MHz DMSO) δ 787 (s 2H) 404 (t J = 72 Hz 4H) 229 (t J = 72 Hz 2H) 13C-NMR (75 MHz DMSO) δ 1360 (s) 1244 (s) 1120 (s) 428 (s) 293 (s)

S7

1c

1H-NMR (300 MHz DMF) δ 797 (s 2H) 739 (dd J = 57 34 Hz 2H) 683 (dd J = 56 34 Hz 2H) 547 (s 4H) 13C-NMR (75 MHz DMSO) δ 1366 (s) 1330(s) 12852 (s) 1268 (s) 1248 (s) 1127 (s) 461 (s)

S8

1d

1H-NMR (300 MHz DMSO) δ 861 (s 2H) 677 (s 2H) 13C-NMR (75 MHz DMSO) δ 1439 (s) 1225 (s) 1127 (s) 1120 (s) 1079 (s) 558 (s)

S9

1e

1H-NMR (300 MHz DMSO) δ 838 (s 2H) 430 (t J = 71 Hz 4H) 248 ndash 233 (m 2H) 13C-NMR (75 MHz DMSO) δ 1433 (s) 1213 (s) 1124(s) 1123(s) 1085 (s) 444 (s) 292 (s)

S10

1f

1H-NMR (300 MHz DMSO) δ 843 (s 2H) 753 (dd J = 57 33 Hz 2H) 722 (dd J = 56 34 Hz 2H) 572 (s 4H) 13C-NMR (75 MHz DMSO) δ 1437 (s) 13223 (s) 1296 (s) 1290 (s) 12220 (s) 1123 (s)1122 (s) 1083 (s) 479 (s)

S11

2a

S12

1H-NMR (300 MHz DMSO) δ 976 (s 2H) 694 (s 2H) 394 (s 6H)

13C- NMR (75 MHz DMSO) δ 1385 (s) 1204 (s) 1190 (s) 558 (s) 355 (s)

19F-NMR (282 MHz DMSO) δ -14896(s) -14901(s)

S13

2b

S14

1H-NMR (500 MHz DMSO) δ 944 (s 2H) 437 (t J = 72 Hz 4H) 386 (s 6H) 242 ndash 229 (m 2H)

13C-NMR (126 MHz DMSO) δ 1365 (s) 1194 (s) 1181 (s) 448 (s) 349 (s) 272 (s)

19F-NMR (282 MHz DMSO) δ -14895(s) -14900(s)

S15

2c

S16

1H-NMR (300 MHz DMSO) δ 931 (s 2H) 753 (dd J = 57 33 Hz 2H) 726 (dd J = 56 34 Hz 2H) 567 (s 4H) 389

(s 6H)

13C-NMR (75 MHz DMSO) δ 1368 (s) 13062 (s) 1297 (s) 1285 (s) 1202 (s) 1185 (s) 484 (s) 352 (s)

19F-NMR (282 MHz DMSO) δ -14891(s) -14897(s)

S17

2e

S18

1H-NMR (300 MHz DMSO) δ 978 (s 2H) 458 (t J = 71 Hz 4H) 411 (s 6H)

13C-NMR (75 MHz DMSO) δ 1425 (s) 1161 (s) 1148 (s) 1060 (s) 472 (s) 372 (s) 277 (s)

19F NMR (282 MHz DMSO) δ -14894(s) -14900(s)

S19

2f

S20

1H-NMR (300 MHz DMSO) δ 965 (s 2H) 768 (dt J = 74 37 Hz 2H) 757 ndash 742 (m 2H) 591 (s 4H) 412 (s 6H)

13C-NMR (75 MHz DMSO) δ 1426 (s) 1307 (s) 1303 (s) 1302 (s) 1171 (s) 1143 (s) 1060 (s) 1059 (s) 505 (s)

372 (s)

19F-NMR (282 MHz DMSO) δ -14897(s) -14903(s)

S21

3a

1H-NMR (600 MHz DMSO) δ 639 (d J = 144 Hz 1H) 604 (d J = 144 Hz 1H) 388 (s 6H)

13C-NMR (151 MHz DMSO) δ 1616 (s) 1172 (s) 1165 (s) 589 (s) 376 (s)

S22

3b

1H-NMR (300 MHz DMSO) δ 495 (dd J = 151 111 Hz 2H) 449 (dd J = 150 58 Hz 2H) 393 (s 6H) 241 (t J = 61

Hz 1H) 188 ndash 165 (m 1H)

13C-NMR (75 MHz DMSO) δ 1170(s) 1164 (s) 549 (s) 501 (s) 368 (s) 285 (s)

S23

3c

1H-NMR (600 MHz DMSO) δ 804 (dd J = 57 35 Hz 2H) 750 (dd J = 57 34 Hz 2H) 665 (d J = 152 Hz 2H) 542

(d J = 153 Hz 2H) 398 (s 6H) 13C-NMR (151 MHz DMSO) δ 1346 (s) 1342 (s) 1184 (s) 1162 (s) 650(s) 516 (s) 374 (s)

S24

3e

1H-NMR (600 MHz DMSO) δ 511 (dd J = 152 115 Hz 2H) 457 (dd J = 150 58 Hz 2H) 413 (s 6H) 228 (dd J =

272 114 Hz 1H)

13C-NMR (151 MHz DMSO) δ 1162 (s) 1155 (s) 1072(s) 1070 (s) 523 (s) 384 (s) 280 (s)

S25

3f

1H-NMR (600 MHz DMSO) δ 795 (dd J = 57 35 Hz 2H) 763 (dd J = 57 34 Hz 2H) 681 (d J = 152 Hz 2H) 571

(d J = 153 Hz 2H) 417 (s 6H)

13C-NMR (151 MHz DMSO) δ 1721 (s) 1343 (s) 1336 (s) 1303 (s) 1181 (s) 1141 (s) 1079 (s) 1069 (s) 528 (s)

S7

1c

1H-NMR (300 MHz DMF) δ 797 (s 2H) 739 (dd J = 57 34 Hz 2H) 683 (dd J = 56 34 Hz 2H) 547 (s 4H) 13C-NMR (75 MHz DMSO) δ 1366 (s) 1330(s) 12852 (s) 1268 (s) 1248 (s) 1127 (s) 461 (s)

S8

1d

1H-NMR (300 MHz DMSO) δ 861 (s 2H) 677 (s 2H) 13C-NMR (75 MHz DMSO) δ 1439 (s) 1225 (s) 1127 (s) 1120 (s) 1079 (s) 558 (s)

S9

1e

1H-NMR (300 MHz DMSO) δ 838 (s 2H) 430 (t J = 71 Hz 4H) 248 ndash 233 (m 2H) 13C-NMR (75 MHz DMSO) δ 1433 (s) 1213 (s) 1124(s) 1123(s) 1085 (s) 444 (s) 292 (s)

S10

1f

1H-NMR (300 MHz DMSO) δ 843 (s 2H) 753 (dd J = 57 33 Hz 2H) 722 (dd J = 56 34 Hz 2H) 572 (s 4H) 13C-NMR (75 MHz DMSO) δ 1437 (s) 13223 (s) 1296 (s) 1290 (s) 12220 (s) 1123 (s)1122 (s) 1083 (s) 479 (s)

S11

2a

S12

1H-NMR (300 MHz DMSO) δ 976 (s 2H) 694 (s 2H) 394 (s 6H)

13C- NMR (75 MHz DMSO) δ 1385 (s) 1204 (s) 1190 (s) 558 (s) 355 (s)

19F-NMR (282 MHz DMSO) δ -14896(s) -14901(s)

S13

2b

S14

1H-NMR (500 MHz DMSO) δ 944 (s 2H) 437 (t J = 72 Hz 4H) 386 (s 6H) 242 ndash 229 (m 2H)

13C-NMR (126 MHz DMSO) δ 1365 (s) 1194 (s) 1181 (s) 448 (s) 349 (s) 272 (s)

19F-NMR (282 MHz DMSO) δ -14895(s) -14900(s)

S15

2c

S16

1H-NMR (300 MHz DMSO) δ 931 (s 2H) 753 (dd J = 57 33 Hz 2H) 726 (dd J = 56 34 Hz 2H) 567 (s 4H) 389

(s 6H)

13C-NMR (75 MHz DMSO) δ 1368 (s) 13062 (s) 1297 (s) 1285 (s) 1202 (s) 1185 (s) 484 (s) 352 (s)

19F-NMR (282 MHz DMSO) δ -14891(s) -14897(s)

S17

2e

S18

1H-NMR (300 MHz DMSO) δ 978 (s 2H) 458 (t J = 71 Hz 4H) 411 (s 6H)

13C-NMR (75 MHz DMSO) δ 1425 (s) 1161 (s) 1148 (s) 1060 (s) 472 (s) 372 (s) 277 (s)

19F NMR (282 MHz DMSO) δ -14894(s) -14900(s)

S19

2f

S20

1H-NMR (300 MHz DMSO) δ 965 (s 2H) 768 (dt J = 74 37 Hz 2H) 757 ndash 742 (m 2H) 591 (s 4H) 412 (s 6H)

13C-NMR (75 MHz DMSO) δ 1426 (s) 1307 (s) 1303 (s) 1302 (s) 1171 (s) 1143 (s) 1060 (s) 1059 (s) 505 (s)

372 (s)

19F-NMR (282 MHz DMSO) δ -14897(s) -14903(s)

S21

3a

1H-NMR (600 MHz DMSO) δ 639 (d J = 144 Hz 1H) 604 (d J = 144 Hz 1H) 388 (s 6H)

13C-NMR (151 MHz DMSO) δ 1616 (s) 1172 (s) 1165 (s) 589 (s) 376 (s)

S22

3b

1H-NMR (300 MHz DMSO) δ 495 (dd J = 151 111 Hz 2H) 449 (dd J = 150 58 Hz 2H) 393 (s 6H) 241 (t J = 61

Hz 1H) 188 ndash 165 (m 1H)

13C-NMR (75 MHz DMSO) δ 1170(s) 1164 (s) 549 (s) 501 (s) 368 (s) 285 (s)

S23

3c

1H-NMR (600 MHz DMSO) δ 804 (dd J = 57 35 Hz 2H) 750 (dd J = 57 34 Hz 2H) 665 (d J = 152 Hz 2H) 542

(d J = 153 Hz 2H) 398 (s 6H) 13C-NMR (151 MHz DMSO) δ 1346 (s) 1342 (s) 1184 (s) 1162 (s) 650(s) 516 (s) 374 (s)

S24

3e

1H-NMR (600 MHz DMSO) δ 511 (dd J = 152 115 Hz 2H) 457 (dd J = 150 58 Hz 2H) 413 (s 6H) 228 (dd J =

272 114 Hz 1H)

13C-NMR (151 MHz DMSO) δ 1162 (s) 1155 (s) 1072(s) 1070 (s) 523 (s) 384 (s) 280 (s)

S25

3f

1H-NMR (600 MHz DMSO) δ 795 (dd J = 57 35 Hz 2H) 763 (dd J = 57 34 Hz 2H) 681 (d J = 152 Hz 2H) 571

(d J = 153 Hz 2H) 417 (s 6H)

13C-NMR (151 MHz DMSO) δ 1721 (s) 1343 (s) 1336 (s) 1303 (s) 1181 (s) 1141 (s) 1079 (s) 1069 (s) 528 (s)

S8

1d

1H-NMR (300 MHz DMSO) δ 861 (s 2H) 677 (s 2H) 13C-NMR (75 MHz DMSO) δ 1439 (s) 1225 (s) 1127 (s) 1120 (s) 1079 (s) 558 (s)

S9

1e

1H-NMR (300 MHz DMSO) δ 838 (s 2H) 430 (t J = 71 Hz 4H) 248 ndash 233 (m 2H) 13C-NMR (75 MHz DMSO) δ 1433 (s) 1213 (s) 1124(s) 1123(s) 1085 (s) 444 (s) 292 (s)

S10

1f

1H-NMR (300 MHz DMSO) δ 843 (s 2H) 753 (dd J = 57 33 Hz 2H) 722 (dd J = 56 34 Hz 2H) 572 (s 4H) 13C-NMR (75 MHz DMSO) δ 1437 (s) 13223 (s) 1296 (s) 1290 (s) 12220 (s) 1123 (s)1122 (s) 1083 (s) 479 (s)

S11

2a

S12

1H-NMR (300 MHz DMSO) δ 976 (s 2H) 694 (s 2H) 394 (s 6H)

13C- NMR (75 MHz DMSO) δ 1385 (s) 1204 (s) 1190 (s) 558 (s) 355 (s)

19F-NMR (282 MHz DMSO) δ -14896(s) -14901(s)

S13

2b

S14

1H-NMR (500 MHz DMSO) δ 944 (s 2H) 437 (t J = 72 Hz 4H) 386 (s 6H) 242 ndash 229 (m 2H)

13C-NMR (126 MHz DMSO) δ 1365 (s) 1194 (s) 1181 (s) 448 (s) 349 (s) 272 (s)

19F-NMR (282 MHz DMSO) δ -14895(s) -14900(s)

S15

2c

S16

1H-NMR (300 MHz DMSO) δ 931 (s 2H) 753 (dd J = 57 33 Hz 2H) 726 (dd J = 56 34 Hz 2H) 567 (s 4H) 389

(s 6H)

13C-NMR (75 MHz DMSO) δ 1368 (s) 13062 (s) 1297 (s) 1285 (s) 1202 (s) 1185 (s) 484 (s) 352 (s)

19F-NMR (282 MHz DMSO) δ -14891(s) -14897(s)

S17

2e

S18

1H-NMR (300 MHz DMSO) δ 978 (s 2H) 458 (t J = 71 Hz 4H) 411 (s 6H)

13C-NMR (75 MHz DMSO) δ 1425 (s) 1161 (s) 1148 (s) 1060 (s) 472 (s) 372 (s) 277 (s)

19F NMR (282 MHz DMSO) δ -14894(s) -14900(s)

S19

2f

S20

1H-NMR (300 MHz DMSO) δ 965 (s 2H) 768 (dt J = 74 37 Hz 2H) 757 ndash 742 (m 2H) 591 (s 4H) 412 (s 6H)

13C-NMR (75 MHz DMSO) δ 1426 (s) 1307 (s) 1303 (s) 1302 (s) 1171 (s) 1143 (s) 1060 (s) 1059 (s) 505 (s)

372 (s)

19F-NMR (282 MHz DMSO) δ -14897(s) -14903(s)

S21

3a

1H-NMR (600 MHz DMSO) δ 639 (d J = 144 Hz 1H) 604 (d J = 144 Hz 1H) 388 (s 6H)

13C-NMR (151 MHz DMSO) δ 1616 (s) 1172 (s) 1165 (s) 589 (s) 376 (s)

S22

3b

1H-NMR (300 MHz DMSO) δ 495 (dd J = 151 111 Hz 2H) 449 (dd J = 150 58 Hz 2H) 393 (s 6H) 241 (t J = 61

Hz 1H) 188 ndash 165 (m 1H)

13C-NMR (75 MHz DMSO) δ 1170(s) 1164 (s) 549 (s) 501 (s) 368 (s) 285 (s)

S23

3c

1H-NMR (600 MHz DMSO) δ 804 (dd J = 57 35 Hz 2H) 750 (dd J = 57 34 Hz 2H) 665 (d J = 152 Hz 2H) 542

(d J = 153 Hz 2H) 398 (s 6H) 13C-NMR (151 MHz DMSO) δ 1346 (s) 1342 (s) 1184 (s) 1162 (s) 650(s) 516 (s) 374 (s)

S24

3e

1H-NMR (600 MHz DMSO) δ 511 (dd J = 152 115 Hz 2H) 457 (dd J = 150 58 Hz 2H) 413 (s 6H) 228 (dd J =

272 114 Hz 1H)

13C-NMR (151 MHz DMSO) δ 1162 (s) 1155 (s) 1072(s) 1070 (s) 523 (s) 384 (s) 280 (s)

S25

3f

1H-NMR (600 MHz DMSO) δ 795 (dd J = 57 35 Hz 2H) 763 (dd J = 57 34 Hz 2H) 681 (d J = 152 Hz 2H) 571

(d J = 153 Hz 2H) 417 (s 6H)

13C-NMR (151 MHz DMSO) δ 1721 (s) 1343 (s) 1336 (s) 1303 (s) 1181 (s) 1141 (s) 1079 (s) 1069 (s) 528 (s)

S9

1e

1H-NMR (300 MHz DMSO) δ 838 (s 2H) 430 (t J = 71 Hz 4H) 248 ndash 233 (m 2H) 13C-NMR (75 MHz DMSO) δ 1433 (s) 1213 (s) 1124(s) 1123(s) 1085 (s) 444 (s) 292 (s)

S10

1f

1H-NMR (300 MHz DMSO) δ 843 (s 2H) 753 (dd J = 57 33 Hz 2H) 722 (dd J = 56 34 Hz 2H) 572 (s 4H) 13C-NMR (75 MHz DMSO) δ 1437 (s) 13223 (s) 1296 (s) 1290 (s) 12220 (s) 1123 (s)1122 (s) 1083 (s) 479 (s)

S11

2a

S12

1H-NMR (300 MHz DMSO) δ 976 (s 2H) 694 (s 2H) 394 (s 6H)

13C- NMR (75 MHz DMSO) δ 1385 (s) 1204 (s) 1190 (s) 558 (s) 355 (s)

19F-NMR (282 MHz DMSO) δ -14896(s) -14901(s)

S13

2b

S14

1H-NMR (500 MHz DMSO) δ 944 (s 2H) 437 (t J = 72 Hz 4H) 386 (s 6H) 242 ndash 229 (m 2H)

13C-NMR (126 MHz DMSO) δ 1365 (s) 1194 (s) 1181 (s) 448 (s) 349 (s) 272 (s)

19F-NMR (282 MHz DMSO) δ -14895(s) -14900(s)

S15

2c

S16

1H-NMR (300 MHz DMSO) δ 931 (s 2H) 753 (dd J = 57 33 Hz 2H) 726 (dd J = 56 34 Hz 2H) 567 (s 4H) 389

(s 6H)

13C-NMR (75 MHz DMSO) δ 1368 (s) 13062 (s) 1297 (s) 1285 (s) 1202 (s) 1185 (s) 484 (s) 352 (s)

19F-NMR (282 MHz DMSO) δ -14891(s) -14897(s)

S17

2e

S18

1H-NMR (300 MHz DMSO) δ 978 (s 2H) 458 (t J = 71 Hz 4H) 411 (s 6H)

13C-NMR (75 MHz DMSO) δ 1425 (s) 1161 (s) 1148 (s) 1060 (s) 472 (s) 372 (s) 277 (s)

19F NMR (282 MHz DMSO) δ -14894(s) -14900(s)

S19

2f

S20

1H-NMR (300 MHz DMSO) δ 965 (s 2H) 768 (dt J = 74 37 Hz 2H) 757 ndash 742 (m 2H) 591 (s 4H) 412 (s 6H)

13C-NMR (75 MHz DMSO) δ 1426 (s) 1307 (s) 1303 (s) 1302 (s) 1171 (s) 1143 (s) 1060 (s) 1059 (s) 505 (s)

372 (s)

19F-NMR (282 MHz DMSO) δ -14897(s) -14903(s)

S21

3a

1H-NMR (600 MHz DMSO) δ 639 (d J = 144 Hz 1H) 604 (d J = 144 Hz 1H) 388 (s 6H)

13C-NMR (151 MHz DMSO) δ 1616 (s) 1172 (s) 1165 (s) 589 (s) 376 (s)

S22

3b

1H-NMR (300 MHz DMSO) δ 495 (dd J = 151 111 Hz 2H) 449 (dd J = 150 58 Hz 2H) 393 (s 6H) 241 (t J = 61

Hz 1H) 188 ndash 165 (m 1H)

13C-NMR (75 MHz DMSO) δ 1170(s) 1164 (s) 549 (s) 501 (s) 368 (s) 285 (s)

S23

3c

1H-NMR (600 MHz DMSO) δ 804 (dd J = 57 35 Hz 2H) 750 (dd J = 57 34 Hz 2H) 665 (d J = 152 Hz 2H) 542

(d J = 153 Hz 2H) 398 (s 6H) 13C-NMR (151 MHz DMSO) δ 1346 (s) 1342 (s) 1184 (s) 1162 (s) 650(s) 516 (s) 374 (s)

S24

3e

1H-NMR (600 MHz DMSO) δ 511 (dd J = 152 115 Hz 2H) 457 (dd J = 150 58 Hz 2H) 413 (s 6H) 228 (dd J =

272 114 Hz 1H)

13C-NMR (151 MHz DMSO) δ 1162 (s) 1155 (s) 1072(s) 1070 (s) 523 (s) 384 (s) 280 (s)

S25

3f

1H-NMR (600 MHz DMSO) δ 795 (dd J = 57 35 Hz 2H) 763 (dd J = 57 34 Hz 2H) 681 (d J = 152 Hz 2H) 571

(d J = 153 Hz 2H) 417 (s 6H)

13C-NMR (151 MHz DMSO) δ 1721 (s) 1343 (s) 1336 (s) 1303 (s) 1181 (s) 1141 (s) 1079 (s) 1069 (s) 528 (s)

S10

1f

1H-NMR (300 MHz DMSO) δ 843 (s 2H) 753 (dd J = 57 33 Hz 2H) 722 (dd J = 56 34 Hz 2H) 572 (s 4H) 13C-NMR (75 MHz DMSO) δ 1437 (s) 13223 (s) 1296 (s) 1290 (s) 12220 (s) 1123 (s)1122 (s) 1083 (s) 479 (s)

S11

2a

S12

1H-NMR (300 MHz DMSO) δ 976 (s 2H) 694 (s 2H) 394 (s 6H)

13C- NMR (75 MHz DMSO) δ 1385 (s) 1204 (s) 1190 (s) 558 (s) 355 (s)

19F-NMR (282 MHz DMSO) δ -14896(s) -14901(s)

S13

2b

S14

1H-NMR (500 MHz DMSO) δ 944 (s 2H) 437 (t J = 72 Hz 4H) 386 (s 6H) 242 ndash 229 (m 2H)

13C-NMR (126 MHz DMSO) δ 1365 (s) 1194 (s) 1181 (s) 448 (s) 349 (s) 272 (s)

19F-NMR (282 MHz DMSO) δ -14895(s) -14900(s)

S15

2c

S16

1H-NMR (300 MHz DMSO) δ 931 (s 2H) 753 (dd J = 57 33 Hz 2H) 726 (dd J = 56 34 Hz 2H) 567 (s 4H) 389

(s 6H)

13C-NMR (75 MHz DMSO) δ 1368 (s) 13062 (s) 1297 (s) 1285 (s) 1202 (s) 1185 (s) 484 (s) 352 (s)

19F-NMR (282 MHz DMSO) δ -14891(s) -14897(s)

S17

2e

S18

1H-NMR (300 MHz DMSO) δ 978 (s 2H) 458 (t J = 71 Hz 4H) 411 (s 6H)

13C-NMR (75 MHz DMSO) δ 1425 (s) 1161 (s) 1148 (s) 1060 (s) 472 (s) 372 (s) 277 (s)

19F NMR (282 MHz DMSO) δ -14894(s) -14900(s)

S19

2f

S20

1H-NMR (300 MHz DMSO) δ 965 (s 2H) 768 (dt J = 74 37 Hz 2H) 757 ndash 742 (m 2H) 591 (s 4H) 412 (s 6H)

13C-NMR (75 MHz DMSO) δ 1426 (s) 1307 (s) 1303 (s) 1302 (s) 1171 (s) 1143 (s) 1060 (s) 1059 (s) 505 (s)

372 (s)

19F-NMR (282 MHz DMSO) δ -14897(s) -14903(s)

S21

3a

1H-NMR (600 MHz DMSO) δ 639 (d J = 144 Hz 1H) 604 (d J = 144 Hz 1H) 388 (s 6H)

13C-NMR (151 MHz DMSO) δ 1616 (s) 1172 (s) 1165 (s) 589 (s) 376 (s)

S22

3b

1H-NMR (300 MHz DMSO) δ 495 (dd J = 151 111 Hz 2H) 449 (dd J = 150 58 Hz 2H) 393 (s 6H) 241 (t J = 61

Hz 1H) 188 ndash 165 (m 1H)

13C-NMR (75 MHz DMSO) δ 1170(s) 1164 (s) 549 (s) 501 (s) 368 (s) 285 (s)

S23

3c

1H-NMR (600 MHz DMSO) δ 804 (dd J = 57 35 Hz 2H) 750 (dd J = 57 34 Hz 2H) 665 (d J = 152 Hz 2H) 542

(d J = 153 Hz 2H) 398 (s 6H) 13C-NMR (151 MHz DMSO) δ 1346 (s) 1342 (s) 1184 (s) 1162 (s) 650(s) 516 (s) 374 (s)

S24

3e

1H-NMR (600 MHz DMSO) δ 511 (dd J = 152 115 Hz 2H) 457 (dd J = 150 58 Hz 2H) 413 (s 6H) 228 (dd J =

272 114 Hz 1H)

13C-NMR (151 MHz DMSO) δ 1162 (s) 1155 (s) 1072(s) 1070 (s) 523 (s) 384 (s) 280 (s)

S25

3f

1H-NMR (600 MHz DMSO) δ 795 (dd J = 57 35 Hz 2H) 763 (dd J = 57 34 Hz 2H) 681 (d J = 152 Hz 2H) 571

(d J = 153 Hz 2H) 417 (s 6H)

13C-NMR (151 MHz DMSO) δ 1721 (s) 1343 (s) 1336 (s) 1303 (s) 1181 (s) 1141 (s) 1079 (s) 1069 (s) 528 (s)

S11

2a

S12

1H-NMR (300 MHz DMSO) δ 976 (s 2H) 694 (s 2H) 394 (s 6H)

13C- NMR (75 MHz DMSO) δ 1385 (s) 1204 (s) 1190 (s) 558 (s) 355 (s)

19F-NMR (282 MHz DMSO) δ -14896(s) -14901(s)

S13

2b

S14

1H-NMR (500 MHz DMSO) δ 944 (s 2H) 437 (t J = 72 Hz 4H) 386 (s 6H) 242 ndash 229 (m 2H)

13C-NMR (126 MHz DMSO) δ 1365 (s) 1194 (s) 1181 (s) 448 (s) 349 (s) 272 (s)

19F-NMR (282 MHz DMSO) δ -14895(s) -14900(s)

S15

2c

S16

1H-NMR (300 MHz DMSO) δ 931 (s 2H) 753 (dd J = 57 33 Hz 2H) 726 (dd J = 56 34 Hz 2H) 567 (s 4H) 389

(s 6H)

13C-NMR (75 MHz DMSO) δ 1368 (s) 13062 (s) 1297 (s) 1285 (s) 1202 (s) 1185 (s) 484 (s) 352 (s)

19F-NMR (282 MHz DMSO) δ -14891(s) -14897(s)

S17

2e

S18

1H-NMR (300 MHz DMSO) δ 978 (s 2H) 458 (t J = 71 Hz 4H) 411 (s 6H)

13C-NMR (75 MHz DMSO) δ 1425 (s) 1161 (s) 1148 (s) 1060 (s) 472 (s) 372 (s) 277 (s)

19F NMR (282 MHz DMSO) δ -14894(s) -14900(s)

S19

2f

S20

1H-NMR (300 MHz DMSO) δ 965 (s 2H) 768 (dt J = 74 37 Hz 2H) 757 ndash 742 (m 2H) 591 (s 4H) 412 (s 6H)

13C-NMR (75 MHz DMSO) δ 1426 (s) 1307 (s) 1303 (s) 1302 (s) 1171 (s) 1143 (s) 1060 (s) 1059 (s) 505 (s)

372 (s)

19F-NMR (282 MHz DMSO) δ -14897(s) -14903(s)

S21

3a

1H-NMR (600 MHz DMSO) δ 639 (d J = 144 Hz 1H) 604 (d J = 144 Hz 1H) 388 (s 6H)

13C-NMR (151 MHz DMSO) δ 1616 (s) 1172 (s) 1165 (s) 589 (s) 376 (s)

S22

3b

1H-NMR (300 MHz DMSO) δ 495 (dd J = 151 111 Hz 2H) 449 (dd J = 150 58 Hz 2H) 393 (s 6H) 241 (t J = 61

Hz 1H) 188 ndash 165 (m 1H)

13C-NMR (75 MHz DMSO) δ 1170(s) 1164 (s) 549 (s) 501 (s) 368 (s) 285 (s)

S23

3c

1H-NMR (600 MHz DMSO) δ 804 (dd J = 57 35 Hz 2H) 750 (dd J = 57 34 Hz 2H) 665 (d J = 152 Hz 2H) 542

(d J = 153 Hz 2H) 398 (s 6H) 13C-NMR (151 MHz DMSO) δ 1346 (s) 1342 (s) 1184 (s) 1162 (s) 650(s) 516 (s) 374 (s)

S24

3e

1H-NMR (600 MHz DMSO) δ 511 (dd J = 152 115 Hz 2H) 457 (dd J = 150 58 Hz 2H) 413 (s 6H) 228 (dd J =

272 114 Hz 1H)

13C-NMR (151 MHz DMSO) δ 1162 (s) 1155 (s) 1072(s) 1070 (s) 523 (s) 384 (s) 280 (s)

S25

3f

1H-NMR (600 MHz DMSO) δ 795 (dd J = 57 35 Hz 2H) 763 (dd J = 57 34 Hz 2H) 681 (d J = 152 Hz 2H) 571

(d J = 153 Hz 2H) 417 (s 6H)

13C-NMR (151 MHz DMSO) δ 1721 (s) 1343 (s) 1336 (s) 1303 (s) 1181 (s) 1141 (s) 1079 (s) 1069 (s) 528 (s)

S12

1H-NMR (300 MHz DMSO) δ 976 (s 2H) 694 (s 2H) 394 (s 6H)

13C- NMR (75 MHz DMSO) δ 1385 (s) 1204 (s) 1190 (s) 558 (s) 355 (s)

19F-NMR (282 MHz DMSO) δ -14896(s) -14901(s)

S13

2b

S14

1H-NMR (500 MHz DMSO) δ 944 (s 2H) 437 (t J = 72 Hz 4H) 386 (s 6H) 242 ndash 229 (m 2H)

13C-NMR (126 MHz DMSO) δ 1365 (s) 1194 (s) 1181 (s) 448 (s) 349 (s) 272 (s)

19F-NMR (282 MHz DMSO) δ -14895(s) -14900(s)

S15

2c

S16

1H-NMR (300 MHz DMSO) δ 931 (s 2H) 753 (dd J = 57 33 Hz 2H) 726 (dd J = 56 34 Hz 2H) 567 (s 4H) 389

(s 6H)

13C-NMR (75 MHz DMSO) δ 1368 (s) 13062 (s) 1297 (s) 1285 (s) 1202 (s) 1185 (s) 484 (s) 352 (s)

19F-NMR (282 MHz DMSO) δ -14891(s) -14897(s)

S17

2e

S18

1H-NMR (300 MHz DMSO) δ 978 (s 2H) 458 (t J = 71 Hz 4H) 411 (s 6H)

13C-NMR (75 MHz DMSO) δ 1425 (s) 1161 (s) 1148 (s) 1060 (s) 472 (s) 372 (s) 277 (s)

19F NMR (282 MHz DMSO) δ -14894(s) -14900(s)

S19

2f

S20

1H-NMR (300 MHz DMSO) δ 965 (s 2H) 768 (dt J = 74 37 Hz 2H) 757 ndash 742 (m 2H) 591 (s 4H) 412 (s 6H)

13C-NMR (75 MHz DMSO) δ 1426 (s) 1307 (s) 1303 (s) 1302 (s) 1171 (s) 1143 (s) 1060 (s) 1059 (s) 505 (s)

372 (s)

19F-NMR (282 MHz DMSO) δ -14897(s) -14903(s)

S21

3a

1H-NMR (600 MHz DMSO) δ 639 (d J = 144 Hz 1H) 604 (d J = 144 Hz 1H) 388 (s 6H)

13C-NMR (151 MHz DMSO) δ 1616 (s) 1172 (s) 1165 (s) 589 (s) 376 (s)

S22

3b

1H-NMR (300 MHz DMSO) δ 495 (dd J = 151 111 Hz 2H) 449 (dd J = 150 58 Hz 2H) 393 (s 6H) 241 (t J = 61

Hz 1H) 188 ndash 165 (m 1H)

13C-NMR (75 MHz DMSO) δ 1170(s) 1164 (s) 549 (s) 501 (s) 368 (s) 285 (s)

S23

3c

1H-NMR (600 MHz DMSO) δ 804 (dd J = 57 35 Hz 2H) 750 (dd J = 57 34 Hz 2H) 665 (d J = 152 Hz 2H) 542

(d J = 153 Hz 2H) 398 (s 6H) 13C-NMR (151 MHz DMSO) δ 1346 (s) 1342 (s) 1184 (s) 1162 (s) 650(s) 516 (s) 374 (s)

S24

3e

1H-NMR (600 MHz DMSO) δ 511 (dd J = 152 115 Hz 2H) 457 (dd J = 150 58 Hz 2H) 413 (s 6H) 228 (dd J =

272 114 Hz 1H)

13C-NMR (151 MHz DMSO) δ 1162 (s) 1155 (s) 1072(s) 1070 (s) 523 (s) 384 (s) 280 (s)

S25

3f

1H-NMR (600 MHz DMSO) δ 795 (dd J = 57 35 Hz 2H) 763 (dd J = 57 34 Hz 2H) 681 (d J = 152 Hz 2H) 571

(d J = 153 Hz 2H) 417 (s 6H)

13C-NMR (151 MHz DMSO) δ 1721 (s) 1343 (s) 1336 (s) 1303 (s) 1181 (s) 1141 (s) 1079 (s) 1069 (s) 528 (s)

S13

2b

S14

1H-NMR (500 MHz DMSO) δ 944 (s 2H) 437 (t J = 72 Hz 4H) 386 (s 6H) 242 ndash 229 (m 2H)

13C-NMR (126 MHz DMSO) δ 1365 (s) 1194 (s) 1181 (s) 448 (s) 349 (s) 272 (s)

19F-NMR (282 MHz DMSO) δ -14895(s) -14900(s)

S15

2c

S16

1H-NMR (300 MHz DMSO) δ 931 (s 2H) 753 (dd J = 57 33 Hz 2H) 726 (dd J = 56 34 Hz 2H) 567 (s 4H) 389

(s 6H)

13C-NMR (75 MHz DMSO) δ 1368 (s) 13062 (s) 1297 (s) 1285 (s) 1202 (s) 1185 (s) 484 (s) 352 (s)

19F-NMR (282 MHz DMSO) δ -14891(s) -14897(s)

S17

2e

S18

1H-NMR (300 MHz DMSO) δ 978 (s 2H) 458 (t J = 71 Hz 4H) 411 (s 6H)

13C-NMR (75 MHz DMSO) δ 1425 (s) 1161 (s) 1148 (s) 1060 (s) 472 (s) 372 (s) 277 (s)

19F NMR (282 MHz DMSO) δ -14894(s) -14900(s)

S19

2f

S20

1H-NMR (300 MHz DMSO) δ 965 (s 2H) 768 (dt J = 74 37 Hz 2H) 757 ndash 742 (m 2H) 591 (s 4H) 412 (s 6H)

13C-NMR (75 MHz DMSO) δ 1426 (s) 1307 (s) 1303 (s) 1302 (s) 1171 (s) 1143 (s) 1060 (s) 1059 (s) 505 (s)

372 (s)

19F-NMR (282 MHz DMSO) δ -14897(s) -14903(s)

S21

3a

1H-NMR (600 MHz DMSO) δ 639 (d J = 144 Hz 1H) 604 (d J = 144 Hz 1H) 388 (s 6H)

13C-NMR (151 MHz DMSO) δ 1616 (s) 1172 (s) 1165 (s) 589 (s) 376 (s)

S22

3b

1H-NMR (300 MHz DMSO) δ 495 (dd J = 151 111 Hz 2H) 449 (dd J = 150 58 Hz 2H) 393 (s 6H) 241 (t J = 61

Hz 1H) 188 ndash 165 (m 1H)

13C-NMR (75 MHz DMSO) δ 1170(s) 1164 (s) 549 (s) 501 (s) 368 (s) 285 (s)

S23

3c

1H-NMR (600 MHz DMSO) δ 804 (dd J = 57 35 Hz 2H) 750 (dd J = 57 34 Hz 2H) 665 (d J = 152 Hz 2H) 542

(d J = 153 Hz 2H) 398 (s 6H) 13C-NMR (151 MHz DMSO) δ 1346 (s) 1342 (s) 1184 (s) 1162 (s) 650(s) 516 (s) 374 (s)

S24

3e

1H-NMR (600 MHz DMSO) δ 511 (dd J = 152 115 Hz 2H) 457 (dd J = 150 58 Hz 2H) 413 (s 6H) 228 (dd J =

272 114 Hz 1H)

13C-NMR (151 MHz DMSO) δ 1162 (s) 1155 (s) 1072(s) 1070 (s) 523 (s) 384 (s) 280 (s)

S25

3f

1H-NMR (600 MHz DMSO) δ 795 (dd J = 57 35 Hz 2H) 763 (dd J = 57 34 Hz 2H) 681 (d J = 152 Hz 2H) 571

(d J = 153 Hz 2H) 417 (s 6H)

13C-NMR (151 MHz DMSO) δ 1721 (s) 1343 (s) 1336 (s) 1303 (s) 1181 (s) 1141 (s) 1079 (s) 1069 (s) 528 (s)

S14

1H-NMR (500 MHz DMSO) δ 944 (s 2H) 437 (t J = 72 Hz 4H) 386 (s 6H) 242 ndash 229 (m 2H)

13C-NMR (126 MHz DMSO) δ 1365 (s) 1194 (s) 1181 (s) 448 (s) 349 (s) 272 (s)

19F-NMR (282 MHz DMSO) δ -14895(s) -14900(s)

S15

2c

S16

1H-NMR (300 MHz DMSO) δ 931 (s 2H) 753 (dd J = 57 33 Hz 2H) 726 (dd J = 56 34 Hz 2H) 567 (s 4H) 389

(s 6H)

13C-NMR (75 MHz DMSO) δ 1368 (s) 13062 (s) 1297 (s) 1285 (s) 1202 (s) 1185 (s) 484 (s) 352 (s)

19F-NMR (282 MHz DMSO) δ -14891(s) -14897(s)

S17

2e

S18

1H-NMR (300 MHz DMSO) δ 978 (s 2H) 458 (t J = 71 Hz 4H) 411 (s 6H)

13C-NMR (75 MHz DMSO) δ 1425 (s) 1161 (s) 1148 (s) 1060 (s) 472 (s) 372 (s) 277 (s)

19F NMR (282 MHz DMSO) δ -14894(s) -14900(s)

S19

2f

S20

1H-NMR (300 MHz DMSO) δ 965 (s 2H) 768 (dt J = 74 37 Hz 2H) 757 ndash 742 (m 2H) 591 (s 4H) 412 (s 6H)

13C-NMR (75 MHz DMSO) δ 1426 (s) 1307 (s) 1303 (s) 1302 (s) 1171 (s) 1143 (s) 1060 (s) 1059 (s) 505 (s)

372 (s)

19F-NMR (282 MHz DMSO) δ -14897(s) -14903(s)

S21

3a

1H-NMR (600 MHz DMSO) δ 639 (d J = 144 Hz 1H) 604 (d J = 144 Hz 1H) 388 (s 6H)

13C-NMR (151 MHz DMSO) δ 1616 (s) 1172 (s) 1165 (s) 589 (s) 376 (s)

S22

3b

1H-NMR (300 MHz DMSO) δ 495 (dd J = 151 111 Hz 2H) 449 (dd J = 150 58 Hz 2H) 393 (s 6H) 241 (t J = 61

Hz 1H) 188 ndash 165 (m 1H)

13C-NMR (75 MHz DMSO) δ 1170(s) 1164 (s) 549 (s) 501 (s) 368 (s) 285 (s)

S23

3c

1H-NMR (600 MHz DMSO) δ 804 (dd J = 57 35 Hz 2H) 750 (dd J = 57 34 Hz 2H) 665 (d J = 152 Hz 2H) 542

(d J = 153 Hz 2H) 398 (s 6H) 13C-NMR (151 MHz DMSO) δ 1346 (s) 1342 (s) 1184 (s) 1162 (s) 650(s) 516 (s) 374 (s)

S24

3e

1H-NMR (600 MHz DMSO) δ 511 (dd J = 152 115 Hz 2H) 457 (dd J = 150 58 Hz 2H) 413 (s 6H) 228 (dd J =

272 114 Hz 1H)

13C-NMR (151 MHz DMSO) δ 1162 (s) 1155 (s) 1072(s) 1070 (s) 523 (s) 384 (s) 280 (s)

S25

3f

1H-NMR (600 MHz DMSO) δ 795 (dd J = 57 35 Hz 2H) 763 (dd J = 57 34 Hz 2H) 681 (d J = 152 Hz 2H) 571

(d J = 153 Hz 2H) 417 (s 6H)

13C-NMR (151 MHz DMSO) δ 1721 (s) 1343 (s) 1336 (s) 1303 (s) 1181 (s) 1141 (s) 1079 (s) 1069 (s) 528 (s)

S15

2c

S16

1H-NMR (300 MHz DMSO) δ 931 (s 2H) 753 (dd J = 57 33 Hz 2H) 726 (dd J = 56 34 Hz 2H) 567 (s 4H) 389

(s 6H)

13C-NMR (75 MHz DMSO) δ 1368 (s) 13062 (s) 1297 (s) 1285 (s) 1202 (s) 1185 (s) 484 (s) 352 (s)

19F-NMR (282 MHz DMSO) δ -14891(s) -14897(s)

S17

2e

S18

1H-NMR (300 MHz DMSO) δ 978 (s 2H) 458 (t J = 71 Hz 4H) 411 (s 6H)

13C-NMR (75 MHz DMSO) δ 1425 (s) 1161 (s) 1148 (s) 1060 (s) 472 (s) 372 (s) 277 (s)

19F NMR (282 MHz DMSO) δ -14894(s) -14900(s)

S19

2f

S20

1H-NMR (300 MHz DMSO) δ 965 (s 2H) 768 (dt J = 74 37 Hz 2H) 757 ndash 742 (m 2H) 591 (s 4H) 412 (s 6H)

13C-NMR (75 MHz DMSO) δ 1426 (s) 1307 (s) 1303 (s) 1302 (s) 1171 (s) 1143 (s) 1060 (s) 1059 (s) 505 (s)

372 (s)

19F-NMR (282 MHz DMSO) δ -14897(s) -14903(s)

S21

3a

1H-NMR (600 MHz DMSO) δ 639 (d J = 144 Hz 1H) 604 (d J = 144 Hz 1H) 388 (s 6H)

13C-NMR (151 MHz DMSO) δ 1616 (s) 1172 (s) 1165 (s) 589 (s) 376 (s)

S22

3b

1H-NMR (300 MHz DMSO) δ 495 (dd J = 151 111 Hz 2H) 449 (dd J = 150 58 Hz 2H) 393 (s 6H) 241 (t J = 61

Hz 1H) 188 ndash 165 (m 1H)

13C-NMR (75 MHz DMSO) δ 1170(s) 1164 (s) 549 (s) 501 (s) 368 (s) 285 (s)

S23

3c

1H-NMR (600 MHz DMSO) δ 804 (dd J = 57 35 Hz 2H) 750 (dd J = 57 34 Hz 2H) 665 (d J = 152 Hz 2H) 542

(d J = 153 Hz 2H) 398 (s 6H) 13C-NMR (151 MHz DMSO) δ 1346 (s) 1342 (s) 1184 (s) 1162 (s) 650(s) 516 (s) 374 (s)

S24

3e

1H-NMR (600 MHz DMSO) δ 511 (dd J = 152 115 Hz 2H) 457 (dd J = 150 58 Hz 2H) 413 (s 6H) 228 (dd J =

272 114 Hz 1H)

13C-NMR (151 MHz DMSO) δ 1162 (s) 1155 (s) 1072(s) 1070 (s) 523 (s) 384 (s) 280 (s)

S25

3f

1H-NMR (600 MHz DMSO) δ 795 (dd J = 57 35 Hz 2H) 763 (dd J = 57 34 Hz 2H) 681 (d J = 152 Hz 2H) 571

(d J = 153 Hz 2H) 417 (s 6H)

13C-NMR (151 MHz DMSO) δ 1721 (s) 1343 (s) 1336 (s) 1303 (s) 1181 (s) 1141 (s) 1079 (s) 1069 (s) 528 (s)

S16

1H-NMR (300 MHz DMSO) δ 931 (s 2H) 753 (dd J = 57 33 Hz 2H) 726 (dd J = 56 34 Hz 2H) 567 (s 4H) 389

(s 6H)

13C-NMR (75 MHz DMSO) δ 1368 (s) 13062 (s) 1297 (s) 1285 (s) 1202 (s) 1185 (s) 484 (s) 352 (s)

19F-NMR (282 MHz DMSO) δ -14891(s) -14897(s)

S17

2e

S18

1H-NMR (300 MHz DMSO) δ 978 (s 2H) 458 (t J = 71 Hz 4H) 411 (s 6H)

13C-NMR (75 MHz DMSO) δ 1425 (s) 1161 (s) 1148 (s) 1060 (s) 472 (s) 372 (s) 277 (s)

19F NMR (282 MHz DMSO) δ -14894(s) -14900(s)

S19

2f

S20

1H-NMR (300 MHz DMSO) δ 965 (s 2H) 768 (dt J = 74 37 Hz 2H) 757 ndash 742 (m 2H) 591 (s 4H) 412 (s 6H)

13C-NMR (75 MHz DMSO) δ 1426 (s) 1307 (s) 1303 (s) 1302 (s) 1171 (s) 1143 (s) 1060 (s) 1059 (s) 505 (s)

372 (s)

19F-NMR (282 MHz DMSO) δ -14897(s) -14903(s)

S21

3a

1H-NMR (600 MHz DMSO) δ 639 (d J = 144 Hz 1H) 604 (d J = 144 Hz 1H) 388 (s 6H)

13C-NMR (151 MHz DMSO) δ 1616 (s) 1172 (s) 1165 (s) 589 (s) 376 (s)

S22

3b

1H-NMR (300 MHz DMSO) δ 495 (dd J = 151 111 Hz 2H) 449 (dd J = 150 58 Hz 2H) 393 (s 6H) 241 (t J = 61

Hz 1H) 188 ndash 165 (m 1H)

13C-NMR (75 MHz DMSO) δ 1170(s) 1164 (s) 549 (s) 501 (s) 368 (s) 285 (s)

S23

3c

1H-NMR (600 MHz DMSO) δ 804 (dd J = 57 35 Hz 2H) 750 (dd J = 57 34 Hz 2H) 665 (d J = 152 Hz 2H) 542

(d J = 153 Hz 2H) 398 (s 6H) 13C-NMR (151 MHz DMSO) δ 1346 (s) 1342 (s) 1184 (s) 1162 (s) 650(s) 516 (s) 374 (s)

S24

3e

1H-NMR (600 MHz DMSO) δ 511 (dd J = 152 115 Hz 2H) 457 (dd J = 150 58 Hz 2H) 413 (s 6H) 228 (dd J =

272 114 Hz 1H)

13C-NMR (151 MHz DMSO) δ 1162 (s) 1155 (s) 1072(s) 1070 (s) 523 (s) 384 (s) 280 (s)

S25

3f

1H-NMR (600 MHz DMSO) δ 795 (dd J = 57 35 Hz 2H) 763 (dd J = 57 34 Hz 2H) 681 (d J = 152 Hz 2H) 571

(d J = 153 Hz 2H) 417 (s 6H)

13C-NMR (151 MHz DMSO) δ 1721 (s) 1343 (s) 1336 (s) 1303 (s) 1181 (s) 1141 (s) 1079 (s) 1069 (s) 528 (s)

S17

2e

S18

1H-NMR (300 MHz DMSO) δ 978 (s 2H) 458 (t J = 71 Hz 4H) 411 (s 6H)

13C-NMR (75 MHz DMSO) δ 1425 (s) 1161 (s) 1148 (s) 1060 (s) 472 (s) 372 (s) 277 (s)

19F NMR (282 MHz DMSO) δ -14894(s) -14900(s)

S19

2f

S20

1H-NMR (300 MHz DMSO) δ 965 (s 2H) 768 (dt J = 74 37 Hz 2H) 757 ndash 742 (m 2H) 591 (s 4H) 412 (s 6H)

13C-NMR (75 MHz DMSO) δ 1426 (s) 1307 (s) 1303 (s) 1302 (s) 1171 (s) 1143 (s) 1060 (s) 1059 (s) 505 (s)

372 (s)

19F-NMR (282 MHz DMSO) δ -14897(s) -14903(s)

S21

3a

1H-NMR (600 MHz DMSO) δ 639 (d J = 144 Hz 1H) 604 (d J = 144 Hz 1H) 388 (s 6H)

13C-NMR (151 MHz DMSO) δ 1616 (s) 1172 (s) 1165 (s) 589 (s) 376 (s)

S22

3b

1H-NMR (300 MHz DMSO) δ 495 (dd J = 151 111 Hz 2H) 449 (dd J = 150 58 Hz 2H) 393 (s 6H) 241 (t J = 61

Hz 1H) 188 ndash 165 (m 1H)

13C-NMR (75 MHz DMSO) δ 1170(s) 1164 (s) 549 (s) 501 (s) 368 (s) 285 (s)

S23

3c

1H-NMR (600 MHz DMSO) δ 804 (dd J = 57 35 Hz 2H) 750 (dd J = 57 34 Hz 2H) 665 (d J = 152 Hz 2H) 542

(d J = 153 Hz 2H) 398 (s 6H) 13C-NMR (151 MHz DMSO) δ 1346 (s) 1342 (s) 1184 (s) 1162 (s) 650(s) 516 (s) 374 (s)

S24

3e

1H-NMR (600 MHz DMSO) δ 511 (dd J = 152 115 Hz 2H) 457 (dd J = 150 58 Hz 2H) 413 (s 6H) 228 (dd J =

272 114 Hz 1H)

13C-NMR (151 MHz DMSO) δ 1162 (s) 1155 (s) 1072(s) 1070 (s) 523 (s) 384 (s) 280 (s)

S25

3f

1H-NMR (600 MHz DMSO) δ 795 (dd J = 57 35 Hz 2H) 763 (dd J = 57 34 Hz 2H) 681 (d J = 152 Hz 2H) 571

(d J = 153 Hz 2H) 417 (s 6H)

13C-NMR (151 MHz DMSO) δ 1721 (s) 1343 (s) 1336 (s) 1303 (s) 1181 (s) 1141 (s) 1079 (s) 1069 (s) 528 (s)

S18

1H-NMR (300 MHz DMSO) δ 978 (s 2H) 458 (t J = 71 Hz 4H) 411 (s 6H)

13C-NMR (75 MHz DMSO) δ 1425 (s) 1161 (s) 1148 (s) 1060 (s) 472 (s) 372 (s) 277 (s)

19F NMR (282 MHz DMSO) δ -14894(s) -14900(s)

S19

2f

S20

1H-NMR (300 MHz DMSO) δ 965 (s 2H) 768 (dt J = 74 37 Hz 2H) 757 ndash 742 (m 2H) 591 (s 4H) 412 (s 6H)

13C-NMR (75 MHz DMSO) δ 1426 (s) 1307 (s) 1303 (s) 1302 (s) 1171 (s) 1143 (s) 1060 (s) 1059 (s) 505 (s)

372 (s)

19F-NMR (282 MHz DMSO) δ -14897(s) -14903(s)

S21

3a

1H-NMR (600 MHz DMSO) δ 639 (d J = 144 Hz 1H) 604 (d J = 144 Hz 1H) 388 (s 6H)

13C-NMR (151 MHz DMSO) δ 1616 (s) 1172 (s) 1165 (s) 589 (s) 376 (s)

S22

3b

1H-NMR (300 MHz DMSO) δ 495 (dd J = 151 111 Hz 2H) 449 (dd J = 150 58 Hz 2H) 393 (s 6H) 241 (t J = 61

Hz 1H) 188 ndash 165 (m 1H)

13C-NMR (75 MHz DMSO) δ 1170(s) 1164 (s) 549 (s) 501 (s) 368 (s) 285 (s)

S23

3c

1H-NMR (600 MHz DMSO) δ 804 (dd J = 57 35 Hz 2H) 750 (dd J = 57 34 Hz 2H) 665 (d J = 152 Hz 2H) 542

(d J = 153 Hz 2H) 398 (s 6H) 13C-NMR (151 MHz DMSO) δ 1346 (s) 1342 (s) 1184 (s) 1162 (s) 650(s) 516 (s) 374 (s)

S24

3e

1H-NMR (600 MHz DMSO) δ 511 (dd J = 152 115 Hz 2H) 457 (dd J = 150 58 Hz 2H) 413 (s 6H) 228 (dd J =

272 114 Hz 1H)

13C-NMR (151 MHz DMSO) δ 1162 (s) 1155 (s) 1072(s) 1070 (s) 523 (s) 384 (s) 280 (s)

S25

3f

1H-NMR (600 MHz DMSO) δ 795 (dd J = 57 35 Hz 2H) 763 (dd J = 57 34 Hz 2H) 681 (d J = 152 Hz 2H) 571

(d J = 153 Hz 2H) 417 (s 6H)

13C-NMR (151 MHz DMSO) δ 1721 (s) 1343 (s) 1336 (s) 1303 (s) 1181 (s) 1141 (s) 1079 (s) 1069 (s) 528 (s)

S19

2f

S20

1H-NMR (300 MHz DMSO) δ 965 (s 2H) 768 (dt J = 74 37 Hz 2H) 757 ndash 742 (m 2H) 591 (s 4H) 412 (s 6H)

13C-NMR (75 MHz DMSO) δ 1426 (s) 1307 (s) 1303 (s) 1302 (s) 1171 (s) 1143 (s) 1060 (s) 1059 (s) 505 (s)

372 (s)

19F-NMR (282 MHz DMSO) δ -14897(s) -14903(s)

S21

3a

1H-NMR (600 MHz DMSO) δ 639 (d J = 144 Hz 1H) 604 (d J = 144 Hz 1H) 388 (s 6H)

13C-NMR (151 MHz DMSO) δ 1616 (s) 1172 (s) 1165 (s) 589 (s) 376 (s)

S22

3b

1H-NMR (300 MHz DMSO) δ 495 (dd J = 151 111 Hz 2H) 449 (dd J = 150 58 Hz 2H) 393 (s 6H) 241 (t J = 61

Hz 1H) 188 ndash 165 (m 1H)

13C-NMR (75 MHz DMSO) δ 1170(s) 1164 (s) 549 (s) 501 (s) 368 (s) 285 (s)

S23

3c

1H-NMR (600 MHz DMSO) δ 804 (dd J = 57 35 Hz 2H) 750 (dd J = 57 34 Hz 2H) 665 (d J = 152 Hz 2H) 542

(d J = 153 Hz 2H) 398 (s 6H) 13C-NMR (151 MHz DMSO) δ 1346 (s) 1342 (s) 1184 (s) 1162 (s) 650(s) 516 (s) 374 (s)

S24

3e

1H-NMR (600 MHz DMSO) δ 511 (dd J = 152 115 Hz 2H) 457 (dd J = 150 58 Hz 2H) 413 (s 6H) 228 (dd J =

272 114 Hz 1H)

13C-NMR (151 MHz DMSO) δ 1162 (s) 1155 (s) 1072(s) 1070 (s) 523 (s) 384 (s) 280 (s)

S25

3f

1H-NMR (600 MHz DMSO) δ 795 (dd J = 57 35 Hz 2H) 763 (dd J = 57 34 Hz 2H) 681 (d J = 152 Hz 2H) 571

(d J = 153 Hz 2H) 417 (s 6H)

13C-NMR (151 MHz DMSO) δ 1721 (s) 1343 (s) 1336 (s) 1303 (s) 1181 (s) 1141 (s) 1079 (s) 1069 (s) 528 (s)

S20

1H-NMR (300 MHz DMSO) δ 965 (s 2H) 768 (dt J = 74 37 Hz 2H) 757 ndash 742 (m 2H) 591 (s 4H) 412 (s 6H)

13C-NMR (75 MHz DMSO) δ 1426 (s) 1307 (s) 1303 (s) 1302 (s) 1171 (s) 1143 (s) 1060 (s) 1059 (s) 505 (s)

372 (s)

19F-NMR (282 MHz DMSO) δ -14897(s) -14903(s)

S21

3a

1H-NMR (600 MHz DMSO) δ 639 (d J = 144 Hz 1H) 604 (d J = 144 Hz 1H) 388 (s 6H)

13C-NMR (151 MHz DMSO) δ 1616 (s) 1172 (s) 1165 (s) 589 (s) 376 (s)

S22

3b

1H-NMR (300 MHz DMSO) δ 495 (dd J = 151 111 Hz 2H) 449 (dd J = 150 58 Hz 2H) 393 (s 6H) 241 (t J = 61

Hz 1H) 188 ndash 165 (m 1H)

13C-NMR (75 MHz DMSO) δ 1170(s) 1164 (s) 549 (s) 501 (s) 368 (s) 285 (s)

S23

3c

1H-NMR (600 MHz DMSO) δ 804 (dd J = 57 35 Hz 2H) 750 (dd J = 57 34 Hz 2H) 665 (d J = 152 Hz 2H) 542

(d J = 153 Hz 2H) 398 (s 6H) 13C-NMR (151 MHz DMSO) δ 1346 (s) 1342 (s) 1184 (s) 1162 (s) 650(s) 516 (s) 374 (s)

S24

3e

1H-NMR (600 MHz DMSO) δ 511 (dd J = 152 115 Hz 2H) 457 (dd J = 150 58 Hz 2H) 413 (s 6H) 228 (dd J =

272 114 Hz 1H)

13C-NMR (151 MHz DMSO) δ 1162 (s) 1155 (s) 1072(s) 1070 (s) 523 (s) 384 (s) 280 (s)

S25

3f

1H-NMR (600 MHz DMSO) δ 795 (dd J = 57 35 Hz 2H) 763 (dd J = 57 34 Hz 2H) 681 (d J = 152 Hz 2H) 571

(d J = 153 Hz 2H) 417 (s 6H)

13C-NMR (151 MHz DMSO) δ 1721 (s) 1343 (s) 1336 (s) 1303 (s) 1181 (s) 1141 (s) 1079 (s) 1069 (s) 528 (s)

S21

3a

1H-NMR (600 MHz DMSO) δ 639 (d J = 144 Hz 1H) 604 (d J = 144 Hz 1H) 388 (s 6H)

13C-NMR (151 MHz DMSO) δ 1616 (s) 1172 (s) 1165 (s) 589 (s) 376 (s)

S22

3b

1H-NMR (300 MHz DMSO) δ 495 (dd J = 151 111 Hz 2H) 449 (dd J = 150 58 Hz 2H) 393 (s 6H) 241 (t J = 61

Hz 1H) 188 ndash 165 (m 1H)

13C-NMR (75 MHz DMSO) δ 1170(s) 1164 (s) 549 (s) 501 (s) 368 (s) 285 (s)

S23

3c

1H-NMR (600 MHz DMSO) δ 804 (dd J = 57 35 Hz 2H) 750 (dd J = 57 34 Hz 2H) 665 (d J = 152 Hz 2H) 542

(d J = 153 Hz 2H) 398 (s 6H) 13C-NMR (151 MHz DMSO) δ 1346 (s) 1342 (s) 1184 (s) 1162 (s) 650(s) 516 (s) 374 (s)

S24

3e

1H-NMR (600 MHz DMSO) δ 511 (dd J = 152 115 Hz 2H) 457 (dd J = 150 58 Hz 2H) 413 (s 6H) 228 (dd J =

272 114 Hz 1H)

13C-NMR (151 MHz DMSO) δ 1162 (s) 1155 (s) 1072(s) 1070 (s) 523 (s) 384 (s) 280 (s)

S25

3f

1H-NMR (600 MHz DMSO) δ 795 (dd J = 57 35 Hz 2H) 763 (dd J = 57 34 Hz 2H) 681 (d J = 152 Hz 2H) 571

(d J = 153 Hz 2H) 417 (s 6H)

13C-NMR (151 MHz DMSO) δ 1721 (s) 1343 (s) 1336 (s) 1303 (s) 1181 (s) 1141 (s) 1079 (s) 1069 (s) 528 (s)

S22

3b

1H-NMR (300 MHz DMSO) δ 495 (dd J = 151 111 Hz 2H) 449 (dd J = 150 58 Hz 2H) 393 (s 6H) 241 (t J = 61

Hz 1H) 188 ndash 165 (m 1H)

13C-NMR (75 MHz DMSO) δ 1170(s) 1164 (s) 549 (s) 501 (s) 368 (s) 285 (s)

S23

3c

1H-NMR (600 MHz DMSO) δ 804 (dd J = 57 35 Hz 2H) 750 (dd J = 57 34 Hz 2H) 665 (d J = 152 Hz 2H) 542

(d J = 153 Hz 2H) 398 (s 6H) 13C-NMR (151 MHz DMSO) δ 1346 (s) 1342 (s) 1184 (s) 1162 (s) 650(s) 516 (s) 374 (s)

S24

3e

1H-NMR (600 MHz DMSO) δ 511 (dd J = 152 115 Hz 2H) 457 (dd J = 150 58 Hz 2H) 413 (s 6H) 228 (dd J =

272 114 Hz 1H)

13C-NMR (151 MHz DMSO) δ 1162 (s) 1155 (s) 1072(s) 1070 (s) 523 (s) 384 (s) 280 (s)

S25

3f

1H-NMR (600 MHz DMSO) δ 795 (dd J = 57 35 Hz 2H) 763 (dd J = 57 34 Hz 2H) 681 (d J = 152 Hz 2H) 571

(d J = 153 Hz 2H) 417 (s 6H)

13C-NMR (151 MHz DMSO) δ 1721 (s) 1343 (s) 1336 (s) 1303 (s) 1181 (s) 1141 (s) 1079 (s) 1069 (s) 528 (s)

S23

3c

1H-NMR (600 MHz DMSO) δ 804 (dd J = 57 35 Hz 2H) 750 (dd J = 57 34 Hz 2H) 665 (d J = 152 Hz 2H) 542

(d J = 153 Hz 2H) 398 (s 6H) 13C-NMR (151 MHz DMSO) δ 1346 (s) 1342 (s) 1184 (s) 1162 (s) 650(s) 516 (s) 374 (s)

S24

3e

1H-NMR (600 MHz DMSO) δ 511 (dd J = 152 115 Hz 2H) 457 (dd J = 150 58 Hz 2H) 413 (s 6H) 228 (dd J =

272 114 Hz 1H)

13C-NMR (151 MHz DMSO) δ 1162 (s) 1155 (s) 1072(s) 1070 (s) 523 (s) 384 (s) 280 (s)

S25

3f

1H-NMR (600 MHz DMSO) δ 795 (dd J = 57 35 Hz 2H) 763 (dd J = 57 34 Hz 2H) 681 (d J = 152 Hz 2H) 571

(d J = 153 Hz 2H) 417 (s 6H)

13C-NMR (151 MHz DMSO) δ 1721 (s) 1343 (s) 1336 (s) 1303 (s) 1181 (s) 1141 (s) 1079 (s) 1069 (s) 528 (s)

S24

3e

1H-NMR (600 MHz DMSO) δ 511 (dd J = 152 115 Hz 2H) 457 (dd J = 150 58 Hz 2H) 413 (s 6H) 228 (dd J =

272 114 Hz 1H)

13C-NMR (151 MHz DMSO) δ 1162 (s) 1155 (s) 1072(s) 1070 (s) 523 (s) 384 (s) 280 (s)

S25

3f

1H-NMR (600 MHz DMSO) δ 795 (dd J = 57 35 Hz 2H) 763 (dd J = 57 34 Hz 2H) 681 (d J = 152 Hz 2H) 571

(d J = 153 Hz 2H) 417 (s 6H)

13C-NMR (151 MHz DMSO) δ 1721 (s) 1343 (s) 1336 (s) 1303 (s) 1181 (s) 1141 (s) 1079 (s) 1069 (s) 528 (s)

S25

3f

1H-NMR (600 MHz DMSO) δ 795 (dd J = 57 35 Hz 2H) 763 (dd J = 57 34 Hz 2H) 681 (d J = 152 Hz 2H) 571

(d J = 153 Hz 2H) 417 (s 6H)

13C-NMR (151 MHz DMSO) δ 1721 (s) 1343 (s) 1336 (s) 1303 (s) 1181 (s) 1141 (s) 1079 (s) 1069 (s) 528 (s)