Supplementary Information. Living Ring-Opening Polymerization of Lactones by N-Heterocyclic Olefin/Al(C 6 F 5 ) 3
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1 Supplementary Information Living Ring-Opening Polymerization of Lactones by N-Heterocyclic Olefin/Al(C 6 F 5 ) 3 Lewis Pairs: Structures of Intermediates, Kinetics, and Mechanism Qianyi Wang, Wuchao Zhao, Jianghua He, and Yuetao Zhang *, and Eugene Y.-X. Chen State Key Laboratory of Supramolecular Structure and Materials, College of Chemistry, Jilin University, Changchun, , China Department of Chemistry, Colorado State University, Fort Collins, Colorado , United States * Corresponding author. s:ytzhang2009@jlu.edu.cn S1
2 Table of Contents Figure S1. 1 H NMR spectrum of NHO1 (25 C, C 6 D 6 )...S4 Figure S2. 13 C NMR spectrum of NHO1 (25 C, C 6 D 6 )...S4 Figure S3. 1 H NMR spectrum of compound 1 (25 C, C 6 D 6 )...S5 Figure S4. 13 C NMR spectrum of compound 1 (25 C, CD 2 Cl 2 )...S5 Figure S5. 1 H NMR spectrum of compound 2 (25 C, C 6 D 6 )...S6 Figure S6. 13 C NMR spectrum of compound 2 (25 C, CD 2 Cl 2 )...S6 Figure S7. 1 H NMR spectrum of 1-hydroxynonan-5-one (25 C, CDCl 3 )...S6 Figure S8. 1 H NMR spectrum of Al(C 6 F 5 ) 3 VL (25 C, C 6 D 6 )... S7 Figure S9. 19 F NMR spectrum of Al(C 6 F 5 ) 3 VL (25 C, C 6 D 6 )... S7 Figure S C NMR spectrum of Al(C 6 F 5 ) 3 VL (25 C, C 6 D 6 )... S7 Figure S11. 1 H NMR spectrum of Al(C 6 F 5 ) 3 CL (25 C, C 6 D 6 )... S8 Figure S F NMR spectrum of Al(C 6 F 5 ) 3 CL (25 C, C 6 D 6 )... S8 Figure S C NMRspectrum of Al(C 6 F 5 ) 3 CL (25 C, C 6 D 6 )... S8 Figure S14. 1 H NMR spectrum of NHO2 Al(C 6 F 5 ) 3 (25 C, C 6 D 6 )... S9 Figure S F NMR spectrum of NHO2 Al(C 6 F 5 ) 3 (25 C, C 6 D 6 )... S9 Figure S16. 1 H NMRspectrum of INT1 (25 C, C 6 D 6 )...S10 Figure S F NMRspectrum of INT1 (25 C, C 6 D 6 )...S10 Figure S C NMRspectrum of INT1 (25 C, C 6 D 6 )...S10 Figure S19. 1 H NMRspectrum of INT2 (25 C, C 6 D 6 )...S11 Figure S F NMRspectrum of INT2 (25 C, C 6 D 6 )...S11 Figure S C NMRspectrum of INT2 (25 C, C 6 D 6 )...S11 Figure S22. 1 H NMR spectrum of INT3 (25 C, C 6 D 6 )... S12 S2
3 Figure S F NMRspectrum of INT3 (25 C, C 6 D 6 )... S12 Figure S C NMRspectrum of INT3 (25 C, CD 2 Cl 2 )...S12 Figure S25. Plots of M n and PDI for PCL and PVL vs [M] 0 /[NHO2] ratio... S13 Figure S26. Plots of M n and PDI of PCL vs ε-cl conversion... S13 Figure S27. 1 H NMR spectrum of Low MW PVL produced by NHO2/Al(C 6 F 5 ) 3 ) system..s14 Scheme S1. Structure of Lewis Base...S15 Table S1. ROP of ε-cl by different Al(C 6 F 5 ) 3 based Lewis pairs...s15 Table S2. Copolymerization of ε-cl and δ-vl by NHO2/Al(C 6 F 5 ) 3 system...s15 Table S3. Crystal data and structure refinement for compound 1, Al(C 6 F 5 ) 3 CL, and INT3...S16 Table S4. Bond lengths [Å] and angles [º] for compound 1...S17 Table S5. Bond lengths [Å] and angles [º] for adduct Al(C 6 F 5 ) 3 CL...S17 Table S6. Bond lengths [Å] and angles [º] for INT3...S19 S3
4 Figure S1. 1 H NMR spectrum of NHO1 (benzene-d 6, 500 MHz). Figure S2. 13 C NMR spectrum of NHO1 (benzene-d 6, 126 MHz). S4
5 Figure S3. 1 H NMR spectrum of compound 1 (benzene-d 6, 500 MHz). Figure S4. 13 C NMR spectrum of compound 1 (CD 2 Cl 2, 126 MHz). S5
6 Figure S5. 1 H NMR spectrum of compound 2 (benzene-d 6, 500 MHz). Figure S6. 13 C NMR spectrum of compound 2 (CD 2 Cl 2, 126 MHz). Figure S7. 1 H NMR spectrum of 1-hydroxynonan-5-one (CDCl 3, 500 MHz). S6
7 Figure S8. 1 H NMR spectrum of Al(C 6 F 5 ) 3 VL (benzene-d 6, 500 MHz). Figure S9. 19 F NMR spectrum of Al(C 6 F 5 ) 3 VL (benzene-d 6, 471 MHz). Figure S C NMR spectrum of Al(C 6 F 5 ) 3 VL (benzene-d 6, 126 MHz). S7
8 Figure S11. 1 H NMR spectrum of Al(C 6 F 5 ) 3 CL (benzene-d 6, 500 MHz). Figure S F NMR spectrum of Al(C 6 F 5 ) 3 CL (benzene-d 6, 471 MHz). Figure S C NMR spectrum of Al(C 6 F 5 ) 3 CL (benzene-d 6, 126 MHz). S8
9 Figure S14. 1 H NMR spectrum of NHO2 Al(C 6 F 5 ) 3 (benzene-d 6, 500 MHz). Figure S F NMR spectrum of NHO2 Al(C 6 F 5 ) 3 (benzene-d 6, 471 MHz). S9
10 Figure S16. 1 H NMR spectrum of INT1 (benzene-d 6, 500 MHz). Note that this sample contained a small amount of hexane (see peaks marked with an asterisk) Figure S F NMR spectrum of reaction of INT1 (benzene-d 6, 471 MHz). Figure S C NMR spectrum of INT1 (benzene-d 6, 126 MHz). S10
11 Figure S19. 1 H NMR spectrum of INT2 (benzene-d 6, 500 MHz). Note that this sample contained a small amount of hexane (see peaks marked with an asterisk) Figure S F NMR spectrum of reaction of INT2 (benzene-d 6, 471 MHz). Figure S C NMR spectrum of INT2 (benzene-d 6, 126 MHz). S11
12 Figure S22. 1 H NMR spectrum of INT3 (benzene-d 6, 500 MHz). Note that this sample contained a small amount of hexane (see peaks marked with an asterisk) Figure S F NMR spectrum of INT3 (benzene-d 6, 471 MHz). Figure S C NMR spectrum of INT3 (CD 2 Cl 2, 126 MHz). S12
13 M n (10 4 g/mol) PCL M n Ð PVL M n Ð R² = R² = [M] 0 /[NHO2] Ð Figure S25. Plots of M n and PDI for PCL and PVL vs [M] 0 /[NHO2] ratio M n (10 4 g/mol) M n Ð R² = Conv. (%) 2 Ð Figure S26. Plots of M n and PDI of PCL vs ε-cl conversion catalyzed by NHO2/ Al(C 6 F 5 ) 3 at room temperature. Conditions: [ε-cl] 0 /[Al(C 6 F 5 ) 3 ]/[NHO2] = 800:2:1. S13
14 Figure S27. 1 H NMR spectrum of Low MW PVL produced by NHO2/Al(C 6 F 5 ) 3 system in toluene at room temperature (benzene-d 6, 500 MHz). S14
15 N N t - Bu N N t - Bu N N N N Ph Ph N N DBU DMAP tbu NHC NHO1 NHO2 Scheme S1. Structure of Lewis Base Table S1. ROP of ε-cl by different Al(C 6 F 5 ) 3 based Lewis pairs a Run LA LB ε-cl :LA:LB Time (hr) Conv. (%) b 1 Al(C 6 F 5 ) 3 0.5Tol DBU 400:2: Al(C 6 F 5 ) 3 0.5Tol DMAP 400:2: Al(C 6 F 5 ) 3 0.5Tol PMes 3 400:2: Al(C 6 F 5 ) 3 0.5Tol tbu NHC 400:2: Al(C 6 F 5 ) 3 0.5Tol NHO1 400:2: Al(C 6 F 5 ) 3 0.5Tol NHO2 400:2: a Carried out at ambient temperature (~ 25 ºC) in toluene (Tol), where [ε-cl] 0 = 1.0 M, [Al(C 6 F 5 ) 3 ] 0 = 5 mm, and [LB] 0 = 2.5 mm for a [ε-cl]:[la]:[lb] ratio of 400:2:1. b Monomer conversions measured by 1 H NMR. Table S2. Copolymerization of ε-cl and δ-vl by NHO2/Al(C 6 F 5 ) 3 system a Run M1/M2 Conv c M w Đ (%) b (10 3 g/mol) 1 200CL/200CL CL: d 200CL and 200VL CL: VL: CL/200VL CL: VL: VL/200CL CL: VL: CL/200VL/200CL CL:100 VL: a Carried out at ambient temperature (~ 25 ºC) in toluene (Tol), where [M] 0 = 1.0 M. b Monomer conversions measured by 1 H NMR. c Absolute molecular weight (M w ) measured by GPC using light scattering detector. d both monomers were added in the same time. S15
16 Table S3. Crystal data and structure refinement for compound 1, Al(C 6 F 5 ) 3 CL, and INT3. Compound 1 Al(C 6 F 5 ) 3 CL INT3 empirical formula C 11 H 18 N 2 O 2 C 24 H 10 AlF 15 O 2 C 52.5 H 43 AlClF 15 N 2O 2 MW wavelength, Å crystal system Triclinic Orthorhombic Triclinic space group P-1 Pbca P-1 a, Å (13) (7) Å (8) b, Å (15) (5) (9) c, Å (16) (7) (15) α, deg (3) (2) β, deg (3) (2) γ, deg (3) (2) V, Å (17) (3) (3) Z D calc, g cm µ, mm F(000) crystal size, mm θ range, deg limiting indices 9 h 9 11 k 8 12 l h k l h k l 27 reflns collected independent reflns 2489 [R(int) = ] 5969 [R(int) = ] [R(int) = ] absorption correction Empirical Empirical Empirical data/restraints/para s 2489 / 0 / / 0 / / 114 / 658 goodness-of-fit on F final R indices R1 = [ I >2σ(I) ] [a] wr2 = R indices (all data) [a] R1 = ; wr2 = R1 = wr2 = R1 = wr2 = R1 = wr2 = R1 = ; wr2 = peak max /hole min (e Å 3 ) / / / [a] R1 = F o F c / F o ; wr2 = { [w(f o 2 F c 2 ) 2 ]/ [w(f o 2 ) 2 ]} 1/2 S16
17 Table S4. Bond lengths [Å] and angles [º] for compound 1. O(1)-C(7) 1.269(2) N(2)-C(5) 1.350(2) N(1)-C(5) 1.358(2) N(2)-C(3) 1.386(3) N(1)-C(2) 1.377(3) N(2)-C(4) 1.458(3) N(1)-C(1) 1.448(3) C(9)-C(8) 1.527(3) C(10)-C(11) 1.519(3) C(11)-O(2) 1.418(2) C(10)-C(9) 1.526(3) C(6)-C(5) 1.423(3) C(7)-C(6) 1.390(3) C(2)-C(3) 1.333(3) C(7)-C(8) 1.525(3) C(5)-N(1)-C(2) (17) C(10)-C(9)-C(8) (16) C(5)-N(1)-C(1) (17) O(2)-C(11)-C(10) (17) C(2)-N(1)-C(1) (17) C(7)-C(6)-C(5) (18) C(11)-C(10)-C(9) (16) N(2)-C(5)-N(1) (16) O(1)-C(7)-C(6) (18) N(2)-C(5)-C(6) (18) O(1)-C(7)-C(8) (17) N(1)-C(5)-C(6) (17) C(6)-C(7)-C(8) (17) C(3)-C(2)-N(1) (18) C(5)-N(2)-C(3) (17) C(2)-C(3)-N(2) (18) C(5)-N(2)-C(4) (17) C(7)-C(8)-C(9) (16) C(3)-N(2)-C(4) (17) Table S5. Bond lengths [Å] and angles [º] for adduct Al(C 6 F 5 ) 3 CL. Al(1)-O(1) (13) C(13)-C(18) 1.379(2) Al(1)-C(7) (16) C(13)-C(14) 1.385(2) Al(1)-C(19) (17) C(14)-F(5) 1.358(2) Al(1)-C(13) (18) C(14)-C(15) 1.380(3) O(1)-C(1) 1.252(2) C(15)-F(4) 1.347(2) O(2)-C(1) 1.294(2) C(15)-C(16) 1.369(3) O(2)-C(2) 1.484(2) C(16)-F(3) 1.341(2) C(1)-C(6) 1.488(2) C(16)-C(17) 1.380(3) C(2)-C(3) 1.510(3) C(17)-F(2) 1.345(2) C(3)-C(4) 1.525(3) C(17)-C(18) 1.377(2) C(4)-C(5) 1.518(3) C(18)-F(1) (19) C(5)-C(6) 1.537(3) C(19)-C(20) 1.382(2) C(7)-C(12) 1.383(2) C(19)-C(24) 1.382(2) C(7)-C(8) 1.388(2) C(20)-F(15) (19) C(8)-F(6) (18) C(20)-C(21) 1.383(2) C(8)-C(9) 1.384(2) C(21)-F(14) 1.347(2) C(9)-F(7) (18) C(21)-C(22) 1.373(2) C(9)-C(10) 1.373(2) C(22)-F(13) (19) C(10)-F(8) (19) C(22)-C(23) 1.374(3) S17
18 C(10)-C(11) 1.376(2) C(23)-F(12) (19) C(11)-F(9) 1.345(2) C(23)-C(24) 1.383(2) C(11)-C(12) 1.378(2) C(24)-F(11) (19) C(12)-F(10) (19) O(1)-Al(1)-C(7) (6) C(18)-C(13)-Al(1) (12) O(1)-Al(1)-C(19) (7) C(14)-C(13)-Al(1) (14) C(7)-Al(1)-C(19) (7) F(5)-C(14)-C(15) (16) O(1)-Al(1)-C(13) (7) F(5)-C(14)-C(13) (17) C(7)-Al(1)-C(13) (7) C(15)-C(14)-C(13) (18) C(19)-Al(1)-C(13) (7) F(4)-C(15)-C(16) (19) C(1)-O(1)-Al(1) (12) F(4)-C(15)-C(14) 120.8(2) C(1)-O(2)-C(2) (14) C(16)-C(15)-C(14) (17) O(1)-C(1)-O(2) (15) F(3)-C(16)-C(15) (18) O(1)-C(1)-C(6) (16) F(3)-C(16)-C(17) 119.8(2) O(2)-C(1)-C(6) (15) C(15)-C(16)-C(17) (17) O(2)-C(2)-C(3) (14) F(2)-C(17)-C(18) (17) C(2)-C(3)-C(4) (15) F(2)-C(17)-C(16) (17) C(5)-C(4)-C(3) (15) C(18)-C(17)-C(16) (18) C(4)-C(5)-C(6) (16) F(1)-C(18)-C(17) (16) C(1)-C(6)-C(5) (15) F(1)-C(18)-C(13) (15) C(12)-C(7)-C(8) (14) C(17)-C(18)-C(13) (16) C(12)-C(7)-Al(1) (12) C(20)-C(19)-C(24) (15) C(8)-C(7)-Al(1) (12) C(20)-C(19)-Al(1) (12) F(6)-C(8)-C(9) (14) C(24)-C(19)-Al(1) (12) F(6)-C(8)-C(7) (14) F(15)-C(20)-C(19) (15) C(9)-C(8)-C(7) (15) F(15)-C(20)-C(21) (15) F(7)-C(9)-C(10) (15) C(19)-C(20)-C(21) (15) F(7)-C(9)-C(8) (15) F(14)-C(21)-C(22) (15) C(10)-C(9)-C(8) (15) F(14)-C(21)-C(20) (15) F(8)-C(10)-C(9) (16) C(22)-C(21)-C(20) (15) F(8)-C(10)-C(11) (16) F(13)-C(22)-C(21) (16) C(9)-C(10)-C(11) (15) F(13)-C(22)-C(23) (15) F(9)-C(11)-C(10) (15) C(21)-C(22)-C(23) (15) F(9)-C(11)-C(12) (16) F(12)-C(23)-C(22) (16) C(10)-C(11)-C(12) (15) F(12)-C(23)-C(24) (16) F(10)-C(12)-C(11) (15) C(22)-C(23)-C(24) (15) F(10)-C(12)-C(7) (14) F(11)-C(24)-C(19) (15) C(11)-C(12)-C(7) (15) F(11)-C(24)-C(23) (15) C(18)-C(13)-C(14) (16) C(19)-C(24)-C(23) (16) S18
19 Table S6. Bond lengths [Å] and angles [º] for INT3. Al(1)-O(1) 1.732(2) Cl(1)-C(48)# (6) Al(1)-C(27) 2.017(3) Cl(1)-C(45) 1.686(6) Al(1)-C(39) 2.035(3) Cl(1)-C(49)# (7) Al(1)-C(33) 2.042(3) Cl(1)-C(47)# (9) F(1)-C(28) 1.360(4) C(45)-C(48)# (9) F(2)-C(29) 1.348(4 C(45)-C(49)# (16) F(3)-C(30) 1.344(4) C(45)-C(47)# (16) F(4)-C(31) 1.344(4) C(45)-C(46) F(5)-C(32) 1.351(4) C(45)-C(50) F(6)-C(34) 1.354(4) C(45)-C(50)# (10) F(7)-C(35) 1.346(4) C(45)-C(46)# (14) F(8)-C(36) 1.347(4) C(46)-C(49)# (12) F(9)-C(37) 1.342(4 C(46)-C(50)# (12) F(10)-C(38) 1.357(4) C(46)-C(47) F(11)-C(40) 1.361(4) C(46)-C(48)# (13) F(12)-C(41) 1.354(4) C(46)-C(45)# (13) F(13)-C(42) 1.342(4) C(47)-C(50)# (11) F(14)-C(43) 1.346(4) C(47)-C(45)# (13) F(15)-C(44) 1.349(4) C(47)-C(48) O(1)-C(1) 1.381(3) C(47)-C(49)# (12) O(2)-C(1) 1.422(4) C(47)-Cl(1)# (8) O(2)-C(2) 1.433(4) C(48)-C(45)# (8) N(1)-C(8) 1.354(4) C(48)-Cl(1)# (5) N(1)-C(9) 1.389(4) C(48)-C(49) N(1)-C(13) 1.468(4) C(48)-C(50)# (14) N(2)-C(8) 1.354(4) C(48)-C(46)# (11) N(2)-C(10) 1.400(4) C(49)-C(46)# (13) N(2)-C(14) 1.473(4) C(49)-C(45)# (12) C(1)-C(6) 1.549(4) C(49)-C(50) C(1)-C(7) 1.578(4) C(49)-C(47)# (13) C(2)-C(3) 1.517(5) C(49)-Cl(1)# (7) C(3)-C(4) 1.520(6) C(50)-C(47)# (11) C(4)-C(5) 1.524(6) C(50)-C(46)# (14) C(5)-C(6) 1.526(5) C(50)-C(48)# (16) C(7)-C(8) 1.534(4) C(50)-C(45)# (8) C(7)-C(12) 1.542(4) Cl(2)-C(54)# (5) C(7)-C(11) 1.543(4) Cl(2)-C(55)# (7) C(9)-C(10) 1.350(4) Cl(2)-C(51) 1.718(5) C(9)-C(15) 1.476(4) Cl(2)-C(53)# (7) C(10)-C(21) 1.476(4) C(51)-C(55)# (11) C(15)-C(20) 1.394(4) C(51)-C(54)# (8) C(15)-C(16) 1.397(4) C(51)-C(56)# (11) S19
20 C(16)-C(17) 1.389(5) C(51)-C(52) C(17)-C(18) 1.379(5) C(51)-C(56) C(18)-C(19) 1.391(5) C(51)-C(53)# (11) C(19)-C(20) 1.382(5) C(51)-C(51)# (8) C(21)-C(26) 1.386(5) C(51)-C(52)# (11) C(21)-C(22) 1.392(4) C(52)-C(56)# (9) C(22)-C(23) 1.389(5) C(52)-C(55)# (10) C(23)-C(24) 1.379(6) C(52)-C(53) C(24)-C(25) 1.390(6) C(52)-C(51)# (9) C(25)-C(26) 1.391(5) C(53)-C(56)# (10) C(27)-C(32) 1.381(5) C(53)-C(54) C(27)-C(28) 1.384(4) C(53)-C(51)# (10) C(28)-C(29) 1.378(4) C(53)-Cl(2)# (6) C(29)-C(30) 1.373(5) C(54)-Cl(2)# (4) C(30)-C(31) 1.366(5) C(54)-C(51)# (8) C(31)-C(32) 1.392(4) C(54)-C(55) C(33)-C(34) 1.383(5) C(55)-C(51)# (9) C(33)-C(38) 1.385(5) C(55)-C(52)# (10) C(34)-C(35) 1.381(5) C(55)-C(56) C(35)-C(36) 1.366(6) C(55)-Cl(2)# (6) C(36)-C(37) 1.380(5) C(56)-C(52)# (11) C(37)-C(38) 1.380(5) C(56)-C(53)# (10) C(39)-C(40) 1.387(4) C(56)-C(51)# (9) C(39)-C(44) 1.397(4) C(57)-C(58) 1.501(9) C(40)-C(41) 1.370(5) C(58)-C(59) 1.465(11) C(41)-C(42) 1.380(5) C(59)-C(60) 1.522(9) C(42)-C(43) 1.375(5) C(60)-C(61) 1.502(11) C(43)-C(44) 1.383(5) O(1)-Al(1)-C(27) (12) C(47)-C(46)-C(45)#1 40.8(3) O(1)-Al(1)-C(39) (12) C(48)#1-C(46)-C(45)#1 93.0(7) C(27)-Al(1)-C(39) (13) C(50)#1-C(47)-C(45)#1 84.6(12) O(1)-Al(1)-C(33) (12) C(50)#1-C(47)-C(48) 109.0(13) C(27)-Al(1)-C(33) (13) C(45)#1-C(47)-C(48) 24.4(4) C(39)-Al(1)-C(33) (14) C(50)#1-C(47)-C(46) 11.1(13) C(1)-O(1)-Al(1) 147.0(2) C(45)#1-C(47)-C(46) 95.6(4) C(1)-O(2)-C(2) 117.0(3) C(48)-C(47)-C(46) C(8)-N(1)-C(9) 110.2(2) C(50)#1-C(47)-C(49)#1 7.9(10) C(8)-N(1)-C(13) 129.0(3) C(45)#1-C(47)-C(49)#1 92.4(5) C(9)-N(1)-C(13) 120.7(2) C(48)-C(47)-C(49)# (5) C(8)-N(2)-C(10) 109.7(2) C(46)-C(47)-C(49)#1 3.3(5) C(8)-N(2)-C(14) 129.8(3) C(50)#1-C(47)-Cl(1)# (14) C(10)-N(2)-C(14) 120.5(3) C(45)#1-C(47)-Cl(1)#1 48.9(4) O(1)-C(1)-O(2) 111.5(2) C(48)-C(47)-Cl(1)#1 24.6(2) S20
21 O(1)-C(1)-C(6) 110.5(2) C(46)-C(47)-Cl(1)# (2) O(2)-C(1)-C(6) 111.5(3) C(49)#1-C(47)-Cl(1)# (5) O(1)-C(1)-C(7) 107.6(2) C(45)#1-C(48)-Cl(1)# (16) O(2)-C(1)-C(7) 102.5(2) C(45)#1-C(48)-C(47) 71.0(13) C(6)-C(1)-C(7) 112.8(2) Cl(1)#1-C(48)-C(47) 124.5(6) O(2)-C(2)-C(3) 112.2(3) C(45)#1-C(48)-C(49) 49.0(13) C(2)-C(3)-C(4) 114.0(3) Cl(1)#1-C(48)-C(49) 115.4(6) C(3)-C(4)-C(5) 114.8(3) C(47)-C(48)-C(49) C(4)-C(5)-C(6) 113.9(3) C(45)#1-C(48)-C(50)#1 51.9(11) C(5)-C(6)-C(1) 118.4(3) Cl(1)#1-C(48)-C(50)# (7) C(8)-C(7)-C(12) 111.1(3) C(47)-C(48)-C(50)#1 19.0(3) C(8)-C(7)-C(11) 110.6(3) C(49)-C(48)-C(50)# (3) C(12)-C(7)-C(11) 105.6(2) C(45)#1-C(48)-C(46)#1 35.2(9) C(8)-C(7)-C(1) 107.5(2) Cl(1)#1-C(48)-C(46)# (7) C(12)-C(7)-C(1) 111.1(3) C(47)-C(48)-C(46)# (5) C(11)-C(7)-C(1) 111.0(3) C(49)-C(48)-C(46)#1 13.8(5) N(1)-C(8)-N(2) 106.2(3) C(50)#1-C(48)-C(46)#1 87.1(4) N(1)-C(8)-C(7) 126.8(3) C(46)#1-C(49)-C(45)# (17) N(2)-C(8)-C(7) 127.0(3) C(46)#1-C(49)-C(48) 131.0(13) C(10)-C(9)-N(1) 107.0(3) C(45)#1-C(49)-C(48) 23.3(5) C(10)-C(9)-C(15) 129.2(3) C(46)#1-C(49)-C(50) 11.1(13) N(1)-C(9)-C(15) 123.8(3) C(45)#1-C(49)-C(50) 96.8(5) C(9)-C(10)-N(2) 107.0(3) C(48)-C(49)-C(50) C(9)-C(10)-C(21) 129.4(3) C(46)#1-C(49)-C(47)#1 7.9(10) N(2)-C(10)-C(21) 123.6(3) C(45)#1-C(49)-C(47)# (8) C(20)-C(15)-C(16) 119.5(3 C(48)-C(49)-C(47)# (5) C(20)-C(15)-C(9) 119.7(3) C(50)-C(49)-C(47)#1 3.3(5) C(16)-C(15)-C(9) 120.8(3) C(46)#1-C(49)-Cl(1)# (15) C(17)-C(16)-C(15) 119.4(3) C(45)#1-C(49)-Cl(1)#1 51.7(5) C(18)-C(17)-C(16) 120.7(3) C(48)-C(49)-Cl(1)#1 28.5(3) C(17)-C(18)-C(19) 120.1(3) C(50)-C(49)-Cl(1)# (3) C(20)-C(19)-C(18) 119.7(3) C(47)#1-C(49)-Cl(1)# (6) C(19)-C(20)-C(15) 120.6(3) C(47)#1-C(50)-C(46)#1 161(2) C(26)-C(21)-C(22) 119.3(3) C(47)#1-C(50)-C(49) 168.9(17) C(26)-C(21)-C(10) 120.2(3) C(46)#1-C(50)-C(49) 7.7(8) C(22)-C(21)-C(10) 120.4(3) C(47)#1-C(50)-C(45) 71.0(17) C(23)-C(22)-C(21) 120.3(3) C(46)#1-C(50)-C(45) 127.6(8) C(24)-C(23)-C(22) 120.1(3) C(49)-C(50)-C(45) C(23)-C(24)-C(25) 120.0(3) C(47)#1-C(50)-C(48)#1 51.9(13) C(24)-C(25)-C(26) 119.9(3) C(46)#1-C(50)-C(48)# (11) C(21)-C(26)-C(25) 120.4(3) C(49)-C(50)-C(48)# (5) C(32)-C(27)-C(28) 113.4(3) C(45)-C(50)-C(48)#1 19.0(5) C(32)-C(27)-Al(1) 126.2(2) C(47)#1-C(50)-C(45)#1 155(2) S21
22 C(28)-C(27)-Al(1) 120.4(2) C(46)#1-C(50)-C(45)#1 43.3(5) F(1)-C(28)-C(29) 116.1(3) C(49)-C(50)-C(45)#1 35.8(4) C(29)-C(28)-C(27) 124.9(3) C(45)-C(50)-C(45)#1 84.3(4) F(2)-C(29)-C(30) 119.3(3) C(48)#1-C(50)-C(45)# (7) F(2)-C(29)-C(28) 121.9(3) C(54)#2-Cl(2)-C(55)#2 57.2(9) C(30)-C(29)-C(28) 118.8(3) C(54)#2-Cl(2)-C(51) 14.3(12) F(3)-C(30)-C(31) 120.3(3) C(55)#2-Cl(2)-C(51) 44.0(3) F(3)-C(30)-C(29) 120.2(3) C(54)#2-Cl(2)-C(53)#2 35.1(9) F(4)-C(31)-C(30) 119.6(3) C(55)#2-Cl(2)-C(53)#2 92.2(2) F(4)-C(31)-C(32) 121.0(3) C(51)-Cl(2)-C(53)#2 48.3(3) C(30)-C(31)-C(32) 119.3(3) C(55)#2-C(51)-C(54)#2 67.3(5) F(5)-C(32)-C(27) 120.2(3) C(55)#2-C(51)-C(56)#2 63.7(5) F(5)-C(32)-C(31) 115.8(3) C(54)#2-C(51)-C(56)# (9) C(27)-C(32)-C(31) 124.0(3) C(55)#2-C(51)-C(52) 57.1(6) C(34)-C(33)-C(38) 113.2(3) C(54)#2-C(51)-C(52) 124.3(7) C(34)-C(33)-Al(1) 122.9(2) C(56)#2-C(51)-C(52) 7.2(4) C(38)-C(33)-Al(1) 123.9(2) C(55)#2-C(51)-C(56) 175.9(8) F(6)-C(34)-C(35) 115.8(3) C(54)#2-C(51)-C(56) 115.6(7) F(6)-C(34)-C(33) 119.9(3) C(56)#2-C(51)-C(56) 113.3(4) C(35)-C(34)-C(33) 124.3(3) C(52)-C(51)-C(56) F(7)-C(35)-C(36) 119.6(3) C(55)#2-C(51)-C(53)# (7) F(7)-C(35)-C(34) 120.8(3) C(54)#2-C(51)-C(53)#2 62.0(4) C(36)-C(35)-C(34) 119.6(3) C(56)#2-C(51)-C(53)# (8) F(8)-C(36)-C(35) 120.2(4) C(52)-C(51)-C(53)# (5) F(8)-C(36)-C(37) 120.5(3) C(56)-C(51)-C(53)#2 53.5(5) C(35)-C(36)-C(37) 119.3(3) C(55)#2-C(51)-C(51)# (9) F(9)-C(37)-C(38) 121.5(3) C(54)#2-C(51)-C(51)# (11) F(9)-C(37)-C(36) 119.8(3) C(56)#2-C(51)-C(51)#2 56.9(4) C(38)-C(37)-C(36) 118.6(3) C(52)-C(51)-C(51)#2 63.7(4) F(10)-C(38)-C(37) 114.8(3) C(56)-C(51)-C(51)#2 56.4(4) F(10)-C(38)-C(33) 120.3(3) C(53)#2-C(51)-C(51)# (8) C(37)-C(38)-C(33) 124.9(3) C(55)#2-C(51)-C(52)# (11) C(40)-C(39)-C(44) 113.1(3) C(54)#2-C(51)-C(52)# (8) C(40)-C(39)-Al(1) 125.6(2) C(56)#2-C(51)-C(52)# (5) C(44)-C(39)-Al(1) 121.1(2) C(52)-C(51)-C(52)# (4) F(11)-C(40)-C(41) 115.5(3) C(56)-C(51)-C(52)#2 3.3(4) F(11)-C(40)-C(39) 119.7(3) C(53)#2-C(51)-C(52)#2 55.8(4) C(41)-C(40)-C(39) 124.8(3) C(51)#2-C(51)-C(52)#2 53.9(4) F(12)-C(41)-C(40) 121.2(3) C(55)#2-C(51)-Cl(2) 62.4(4) F(12)-C(41)-C(42) 119.2(3) C(54)#2-C(51)-Cl(2) 5.3(4) C(40)-C(41)-C(42) 119.6(3) C(56)#2-C(51)-Cl(2) 126.1(5) F(13)-C(42)-C(43) 120.3(3) C(52)-C(51)-Cl(2) 119.5(3) F(13)-C(42)-C(41) 120.9(3) C(56)-C(51)-Cl(2) 120.5(3) S22
23 C(43)-C(42)-C(41) 118.8(3) C(53)#2-C(51)-Cl(2) 67.0(3) F(14)-C(43)-C(42) 119.5(3) C(51)#2-C(51)-Cl(2) 175.6(7) F(14)-C(43)-C(44) 120.9(3) C(52)#2-C(51)-Cl(2) 122.8(4) C(42)-C(43)-C(44) 119.5(3) C(56)#2-C(52)-C(55)#2 133(4) F(15)-C(44)-C(43) 115.8(3) C(56)#2-C(52)-C(53) 41(3) F(15)-C(44)-C(39) 120.1(3) C(55)#2-C(52)-C(53) 174.8(6) C(43)-C(44)-C(39) 124.1(3) C(56)#2-C(52)-C(51) 84(4) C(48)#1-Cl(1)-C(45) 5.2(8) C(55)#2-C(52)-C(51) 55.7(6) C(48)#1-Cl(1)-C(49)#1 36.1(4) C(53)-C(52)-C(51) C(45)-Cl(1)-C(49)#1 30.9(4) C(56)#2-C(52)-C(51)#2 28(4) C(48)#1-Cl(1)-C(47)#1 30.9(4) C(55)#2-C(52)-C(51)# (8) C(45)-Cl(1)-C(47)#1 36.2(4) C(53)-C(52)-C(51)#2 57.6(3) C(49)#1-Cl(1)-C(47)# (16) C(51)-C(52)-C(51)#2 62.4(3) C(48)#1-C(45)-C(49)#1 108(2) C(56)#2-C(53)-C(52) 5.2(4) C(48)#1-C(45)-C(47)#1 84.6(16) C(56)#2-C(53)-C(54) 115.6(4) C(49)#1-C(45)-C(47)# (9) C(52)-C(53)-C(54) C(48)#1-C(45)-C(46) 131.0(19) C(56)#2-C(53)-C(51)#2 62.0(4) C(49)#1-C(45)-C(46) 23.3(6) C(52)-C(53)-C(51)#2 66.5(3) C(47)#1-C(45)-C(46) 144.3(5) C(54)-C(53)-C(51)#2 53.5(3) C(48)#1-C(45)-C(50) 109.0(19) C(56)#2-C(53)-Cl(2)# (5) C(49)#1-C(45)-C(50) 143.2(6) C(52)-C(53)-Cl(2)# (2) C(47)#1-C(45)-C(50) 24.4(5) C(54)-C(53)-Cl(2)#2 11.3(2) C(48)#1-C(45)-Cl(1) 10.3(15) C(51)#2-C(53)-Cl(2)#2 64.7(3) C(49)#1-C(45)-Cl(1) 97.4(7) Cl(2)#2-C(54)-C(55) 106.2(9) C(47)#1-C(45)-Cl(1) 94.9(4) C(51)#2-C(54)-C(55) 55.7(4) C(46)-C(45)-Cl(1) 120.7(4) Cl(2)#2-C(54)-C(53) 133.6(9) C(50)-C(45)-Cl(1) 119.3(4) C(51)#2-C(54)-C(53) 64.4(4) C(48)#1-C(45)-C(50)#1 155(2) C(55)-C(54)-C(53) C(47)#1-C(45)-C(50)# (7) C(51)#2-C(55)-C(52)#2 67.3(4) C(46)-C(45)-C(50)#1 24.3(4) C(51)#2-C(55)-C(56) 63.0(4) C(50)-C(45)-C(50)#1 95.7(4) C(52)#2-C(55)-C(56) 5.2(5) Cl(1)-C(45)-C(50)# (6) C(51)#2-C(55)-C(54) 57.1(4) C(48)#1-C(45)-C(46)# (19) C(52)#2-C(55)-C(54) 124.3(4) C(49)#1-C(45)-C(46)# (6) C(56)-C(55)-C(54) C(47)#1-C(45)-C(46)#1 43.5(4) C(51)#2-C(55)-Cl(2)#2 73.6(4) C(46)-C(45)-C(46)# (3) C(52)#2-C(55)-Cl(2)# (6) C(50)-C(45)-C(46)#1 19.2(3) C(56)-C(55)-Cl(2)# (2) Cl(1)-C(45)-C(46)# (5) C(54)-C(55)-Cl(2)#2 16.6(2) C(50)#1-C(45)-C(46)#1 76.6(4) C(52)#2-C(56)-C(53)#2 133(3) C(49)#1-C(46)-C(50)#1 161(2) C(52)#2-C(56)-C(51)#2 89(3) C(49)#1-C(46)-C(45) 49.0(15) C(53)#2-C(56)-C(51)# (9) C(50)#1-C(46)-C(45) 112.4(8) C(52)#2-C(56)-C(55) 41(3) C(49)#1-C(46)-C(47) 168.9(15) C(53)#2-C(56)-C(55) 174.8(7) S23
24 C(50)#1-C(46)-C(47) 7.7(8) C(51)#2-C(56)-C(55) 53.4(4) C(45)-C(46)-C(47) C(52)#2-C(56)-C(51) 149(4) C(49)#1-C(46)-C(48)#1 35.2(10) C(53)#2-C(56)-C(51) 64.4(6) C(50)#1-C(46)-C(48)# (12) C(51)#2-C(56)-C(51) 66.7(4) C(45)-C(46)-C(48)#1 13.8(5) C(55)-C(56)-C(51) C(47)-C(46)-C(48)# (5) C(59)-C(58)-C(57) 114.0(6) C(49)#1-C(46)-C(45)# (17) C(58)-C(59)-C(60) 114.4(5) C(50)#1-C(46)-C(45)#1 33.3(6) C(61)-C(60)-C(59) 114.2(6) C(45)-C(46)-C(45)#1 79.2(3) Symmetry transformations used to generate equivalent atoms: #1 -x+1,-y-1,-z #2 -x-1,-y,-z+1 S24
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