J. Org. Chem., 1998, 63(13), , DOI: /jo980296f

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1 J. Org. Chem., 1998, 63(13), , DOI: /jo980296f Terms & Conditions Electronic Supporting Information files are available without a subscription to ACS Web Editions. The American Chemical Society holds a copyright ownership interest in any copyrightable Supporting Information. Files available from the ACS website may be downloaded for personal use only. Users are not otherwise permitted to reproduce, republish, redistribute, or sell any Supporting Information from the ACS website, either in whole or in part, in either machinereadable form or any other form without permission from the American Chemical Society. For permission to reproduce, republish and redistribute this material, requesters must process their own requests via the RightsLink permission system. Information about how to use the RightsLink permission system can be found at Copyright 1998 American Chemical Society

2 vi"6 American onemicai zociety journai ui urganic enemistry voi rage oj4 nvans 3upplemental rage I J. Am. Chem. Soc. Supporting Information page SI An Improved Procedure for the Preparation of 2,2-Bis[2-[4(S)-tert-butyl-1,3- oxazolinyl] I propane ((SS)-tert-Butyl-Bis(Oxazoline)) and Derived Copper(II) Complexes David A. Evans*, Gretchen S. Peterson, Jeffrey S. Johnson, David M. Barnes, Kevin R. Campos, and K. A. Woerpel Department of Chemistry & Chemical Biology, Harvard University, Cambridge, Massachusetts Supporting Information Crystal data and structure factors for 10 are provided on the following pages. 0 Me e 2 2 SbF 6 Me 3 CH 2 O 10 OH 2 CMe3 10 F22 Cul N2 C6 N1 04 C12 03 F7 Figure 1. Crystallographic structure of the bis(aquo) complexe 10. Selected bond lengths and dihedral angles: Cul-N1 (1.913), Cul-N2 (1.905), Cul-03 (1.994), Cul-04 (1.980), Cul-010/F22 (3.300), Cul-07/F7 (3.500), 03-Cul-N1-C6 (30.00), 04-Cul-N2-C12 (36.00)

3 2 ON 0 -I (b 0 C12 C13

4 v±wo American Lnemical 3ociety jouma ui urgani Lnemistry vo3 rage odql Tvans 3upplemental rage 3 J. Org. Chem. Supportig Information page S3

5 vi"6 American onemicai zociety journai ui urganic enemistry voi rage oj4 nvans 3upplemental rage 4 J. Org. Chem. Supportig Information page S4 Table 1. Crystal data and structure refinement for 1. Identification code test1 Empirical formula Formula weight Temperature Wavelength Crystal system Space group C 1 8 H 3 6 C1 2 CuF 1 2 N Sb (2) K A Monoclinic. P2(1) Unit cell Volume, Z dimensions a = 9.731(2) A alpha 900 b = (4) A beta 91.81(3)0 c = (3) A gamma (1) A 3, 4 Density (calculated) Absorption coefficient F(000) Crystal size E) range for data collection Limiting indices Reflections collected Independent reflections mg/mm mm x 0.08 x 0.06 mm 1.23 to h512, -265k 26, [Rint = ] Absorption correction Semi-empirical from psi-scans Max. and min. transmission Refinement method Data / restraints / parameters Goodness-of-fit on F 2 Final R indices [1>20(1)3 R indices (all data) and Full-matrix least-squares on F / 13 / R1 = , wr2 = R1 = , wr2 = Absolute structure Largest diff. parameter peak and hole 0.00(3) and ea- 3

6 vt16 American onemicai 3ociety joumai ui urganic nemistry voi rage od 4 i evans 3upplemental rage D J. Org. Chem. Supportig Information page SS 4 Table 2. Atomic coordinates [ x 10 ] and equivalent isotropic displacement parameters [A2 x for 1. U(eq) is defined as one third of the trace of the orthogonalized U tensor. x y z U(eq) Cu (1) Cu (2) Sb (1) Sb (3) Sb (4) F (1) F (2) F (3) F (4) F (5) F (6) F (13) F (14) F (15) F (16) F (17) F (18) F (19) F (20) F (21) F (22) F (23) F (24) 0(1) 0(2) 0(3) 0(4) 0 (la) O (2A) " (3A) O (4A) N(1) N(2) N(1A) N(2A) C(1) C(2) C (3) C(4) C(5) C(6) C (7) C(8) C(9) C(10) C(11) C (12) 6736(2) (2) 3508(2) 8648 (1) 9674(1) 2707 (35) 2010 (18) 4440(21) 4842 (19) 2701(12) 4313 (25) 7817 (12) 8685 (15) 9584 (14) 8765 (16) (12) 6958 (12) 7810(11) 9280 (19) (12) 9404(13) (15) 9917 (12) 9227 (11) 7463(12) 5743 (12) 6331(11) (12) (12) (11) (13) 8019 (13) 6734 (13) 12982(11) (12) 8475 (16) 8507 (17) 7521(16) 9970 (16) 8061(20) 8569 (19) 9138 (20) 9657 (18) 9093 (21) (22) 10888(18) 5817 (17) 7805(1) 7773(1) 9566(1) 9627 (1) 7419 (1) 8788(9) 9897 (12) 9535 (9) 9029 (9) 9587 (8) 10291(10) 9634 (6) 8749 (6) 9581(7) (6) 9604 (10) 9640(7) 7579 (8) 6601(7) 7268 (7) 7697 (8) 8246 (5) 7162 (6) 7187 (5) 5895(4) 8554 (5) 8100 (5) 7172 (5) 5903 (5) 8494 (5) 8122 (5) 7704(6) 6916 (6) 7686(6) 6883 (6) 7156 (8) 6505 (7) 6464 (7) 6372 (9) 6008(7) 8240 (8) 7854 (9) 8616 (8) 8978 (8) 9140 (9) 8202(8) 6573 (7) 7912(1) 2783 (1) 9116 (1) 4008(1) (1) 8893 (17) 8632(11) 8157 (7) 9545 (8) (7) 9380 (14) 5020 (6) 4032 (12) 3063 (7) 4046 (10) 4517 (8) 3503 (7) (8) 9892 (11) (8) 9184 (7) (8) (7) 6129 (6) 8207(7) 7422 (7) 9016 (6) 1171(7) 3254 (7) 2258(6) 3850 (7) 7070 (7) 8181(7) 2020 (8) 3134 (7) 6799 (9) 7178 (9) 7856(9) 7527 (12) 6559 (10) 6534 (9) 5824 (10) 7012(11) 7722 (12) 6431(13) 7318(13) 8775 (10) 37 (1) 39 (1) 66 (1) 54 (1) 52 (1) 274(17) 198 (10) 169 (9) 160 (8) 102 (4) 254 (16) 88(3) 131(7) 103 (4) 123 (6) 139 (6) 105 (4) 119 (6) 140 (7) 108 (4) 110 (5) 96 (4) 89 (4) 50(3) 51(3) 58(3) 52 (3) 57 (3) 51(3) 53 (3) 58(3) 38(3) 35(3) 38(3) 29 (3) 37 (4) 37 (4) 35(4) 62 (5) 57 (5) 47 (5) 61(5) 53 (5) 70(6) 78(7) 66(6) 44(4)

7 vi"6 American onemicai zociety journai ui urganic enemistry voi rage oj4 nvans 3upplemental rage o J. Org. Chem. Supportig Information page S6 c(13) C(14) c(15) C(16) C(17) C(1A) C(2A) C(3A) C(4A) c(5a) c(6a) C(7A) c(8a) c(9a) c(10a) c(11a) c (12A) C (13A) C (14A) C (15A) C (16A) C (17A) C(1S) Cl (1) Cl (2) C(2S) cl(3) Cl (4) Sb (2) F(7) F(8) F(9) F(10) F(11) F(12) 6595(16) 4306(18) 3488(21) 3686(16) 4184(22) 13514(15) 13355(17) 12418(16) 14844(18) 12779(20) 13674(18) 14339(16) 14670(17) 13885(20) 15301(22) 15787(17) 10796(16) 11586(17) 9232(17) 8533(21) 8547(16) 9116(19) 3925(33) 4266(11) 4807(9) -425(21) -455(10) -2088(6) 4451(1) 4490(20) 4304(18) 5793(27) 3000(26) 5765(20) 3067(20) 5955(8) 6498(8) 6191(10) 7169(8) 6097(9) 7142(8) 6489(8) 6487(8) 6278(8) 6012(8) 8220(8) 7827(7) 8603(8) 8943(9) 9118(10) 8181(9) 6585(7) 5980(7) 6473(8) 6169(9) 7120(9) 6024(8) 9725(11) 9715(3) 10494(4) 9856(14) 9818(3) 9614(4) 7552(1) 7947(12) 7238(13) 7061(8) 7068(13) 8100(14) 8110(11) 8894(11) 8438(11) 9147(13) 8268(11) 7686(13) 1804(10) 2197(12) 2862(10) 2446(12) 1504(11) 1556(10) 880(9) 2095(10) 2769(11) 1581(14) 2459(12) 3773(9) 3971(10) 3500(10) 4207(11) 3270(11) 2777(11) 5030(15) 6219(4) 4877(6) 10089(14) 11186(4) 9764(4) 5251(1) 6229(10) 4246(9) 5596(19) 5528(14) 5017(19) 4961(14) 50(s) 52(5) 77(7) 61(s) 73(6) 35(4) 54(5) 39(4) 63(5) 64(5) 45(4) 44(4) 46(4) 65(6) 85(7) 65(6) 39(4) 49(4) 45(4) 69(6) 64(6) 56(5) 139(10) 151(4) 147(3) 100(8) 141(3) 98(2) 62(1) 193(10) 204(11) 288(19) 245(14) 273(16) 220(13)

8 IYYO I-111d1 lla R1d1 13uuArL JuiInaidil J'ilgalnu~~11~~' V Uz' ragr, Ui-t1 IA L ani OUPPRIflU1Ld1 radgr / J. Org. Chem. Supportig Information page S7 Table 3. Bond lengths [A] and angles [ ] for 1. Cu(1) -N(2) Cu(1) -0(4) Cu(1)-F(22) Cu(2)-N(1A) Cu(2)-0(3A) ab(1) -F(6) Sb(1) -F(1) Sb(1) -F(5) Sb(3)-F(18) Sb(3)-F(15) Sb(3) -F(17) Sb(4)-F(20) Sb(4)-F(23) Sb(4)-F(24) 0(1) -C(1) 0(2) -C(3) o(1a)-c(1a) 0(2A)-C(3A) N(1) -C(1) N(2) -C(3) N(1A)-C(1A) N(2A)-C(3A) c(1) -C(2) C(2) -C(5) c(6) -C(8) C(8) -C(9) c(8) -c(10) C(12)-C(14) C(14)-C(16) C(1A)-C(2A) C(2A)-C(4A) C(6A)-C(8A) C(8A) -C(11A) C(8A)-C(9A) C(12A) -c(14a) C(14A)-C(17A) 0(18)-01(2) C(2S)-C1(4) Sb(2)-F(9) Sb(2)-F(8) sb(2)-f(7) 1.905(12) 1.980(10) 3.300(11) 1.933(12) 1.958(10) (14) 1.83(2) 1.855(11) 1.822(11) 1.840(11) 1.874(12) 1.838(13) 1.854(11) 1.864(10) 1.35(2) 1.32(2) 1.35(2) 1.38(2) 1.31(2) 1.34(2) 1.30(2) 1.24(2) 1.49(2) 1.51(2) 1.52(2) 1.51(2) 1.58(2) 1.56(2) 1.54(2) 1.52(2) 1.56(2) 1.52(2) 1.51(2) 1.54(2) 1.59(2) 1.52(2) 1.84(3) 1.76(2) 1.74(2) 1.791(14) 1.817(14) Cu(1) -N(1) Cu(1) -0(3) Cu(1) -F(7) Cu(2)-N(2A) Cu(2)-0(4A) Sb(1) -F(2) Sb(1) -F(4) Sb(1) -F(3) Sb(3) -F(14) Sb(3) -F(16) sb(3) -F(13) Sb (4) -F (21) Sb(4)-F(22) Sb(4) -F(19) 0(1) -C(7) 0(2) -C(13) O(1A)-C(7A) 0(2A) -C(13A) N(1) -c(6) N(2) -C(12) N(1A)-C(6A) N(2A) -C(12A) C(2) -C(3) C(2) -C(4) C(6) -C(7) c(8) -c(11) C(12) -C(13) C(14)-C(17) C(14) -C(15) C(2A)-C(3A) C(2A)-C(5A) C(6A)-C(7A) C(8A) -C(10A) C(12A) -C(13A) C(14A) -C(15A) C(14A) -C(16A) C(1s)-Cl(1) C(2S)-C1(3) Sb(2) -F(11) Sb(2)-F(10) sb(2)-f(12) 1.913(12) 1.994(10) 3.50(2) 1.942(12) 1.973(11) 1.782(14) 1.838(13) 1.856(13) (12) 1.845(12) 1.885(11) 1.842(11) 1.861(11) 1.864(10) 1.48(2) 1.44(2) 1.45(2) 1.48(2) 1.53 (2) 1.53(2) 1.52(2) 1.47(2) 1.50(2) 1.55(2) 1.54(2) 1.55(2) 1.50(2) 1.50(3) 1.58(2) 1.45(2) 1.61(2) 1.54(2) 1.51(2) 1.51(2) 1.51(2) 1.55(2) 1.99(3) 1.82(2) 1.77(2) 1.81(2) 1.83(2) N(2)-cu(1)-N(1) N(1) -Cu(1) -0(4) N(1) -cu(1) -0(3) N(2) -Cu(1) -F(22) o(4) -cu(1) -F(22) N(2) -Cu(1) -F(7) 0(4) -Cu(1) -F(7) F(22)-Cu(1)-F(7) N(1A)-Cu(2)-0(3A) N(1A) -Cu(2) -0(4A) 0(3A) -Cu(2) -0(4A) F(6) -Sb(1) -F(1) 94.0(5) 149.5(5) 96.2(5) 77.9(5) 66.8(4) 105.3(6) 124.9(5) 166.8(4) 97.4(5) 143.8(5) 90.0(5) 176.8(13) N(2) -Cu(1) -0(4) N(2) -Cu(1) -0(3) 0(4) -Cu(1) -0(3) N(1)-Cu(1)-F(22) 0(3)-Cu(1)-F(22) N(1)-Cu(1)-F(7) 0(3) -Cu(1) -F(7) N(1A) -Cu(2) -N(2A) N(2A)-Cu(2)-0(3A) N(2A) -Cu(2) -0(4A) F(6)-Sb(1)-F(2) F(2)-Sb(1)-F(1) 94.8(5) 148.4(5) 91.5(5) 86.6(4) 132.5(4) 80.4(5) 47.7(5) 95.2(5) 151.0(5) 95.2(5) 97.5(13) 85.1(13)

9 U 199 American Lhemical society Journal UI Urganic uhemistry V6.5 Fage 6D41 Evans Supplemental Page z5 J. Org. Chem. Supportig Information page S8 F(6) -Sb(1) -F(4) F(1) -Sb(1) -F(4) F(2) -Sb (1)-F (5) F(4) -sb(1) -F(5) F(2)-Sb(1)-F(3) F (4) -Sb (1)-F (3) F(18)-Sb(3)-F(14) F(14) -Sb(3) -F(15) F(14) -Sb(3) -F(16) F(18) -Sb (3) -F(17) F(15)-Sb(3)-F(17) F(18) -Sb(3) -F(13) F(15) -Sb(3) -F(13) F(17)-Sb(3)-F(13) F(20)-Sb(4)-F(23) F(20) -Sb(4) -F(22) F(23) -Sb(4) -F(22) F(21) -Sb(4) -F(24) F(22)-Sb (4) -F(24) F(21) -sb(4) -F(19) F(22) -sb(4) -F(19) Sb(4)-F(22)-Cu(1) C(3) -0(2) -C(13) C(3A) -0(2A) -C(13A) C(1) -N(1) -cu(1) C(3) -N(2) -C(12) C(12) -N(2) -Cu(1) C(1A) -N(1A) -Cu(2) C(3A) -N(2A) -C(12A) C(12A) -N(2A) -Cu(2) N(1)-C(1) -C(2) C(1) -C(2) -C(3) C(3) -C(2) -C(5) C(3) -C(2) -c(4) 0(2) -C(3) -N(2) N(2)-C(3) -C(2) C(8)-C(6) -C(7) 0(1) -C(7) -C(6) c(9) -c(8) -c(11) c(9) -c(8) -c(10) C(11) -C(8) -c(10) c(13)-c(12)-c(14) 0(2) -c(13) -C(12) c(17)-c(14)-c(12) c(17)-c(14)-c(1s) c(12)-c(14)-c(15) N(1A) -C(1A) -C(2A) c(3a)-c(2a)-c(1a) C(1A) -C(2A) -c(4a) c(1a) -c(2a) -C(5A) N(2A) -C(3A) -0(2A) 0(2A) -C(3A) -C(2A) N(1A) -C(6A) -C(7A) 0(1A) -C(7A) -C(6A) C(11A)-c(8A)-C(6A) C(11A) -C(8A) -C(9A) c(6a) -c(8a) -C(9A) N(2A) -C(12A) -C(14A) 97.1(13) 80.3(11) 91.7(8) 89.1(6) 92.5(8) 87.2(7) 92.4(7) 87.5(7) 174.5(8) 179.1(7) 85.2(6) 90.1(6) 175.0(6) 90.5(5) 178.9(8) 88.0(8) 91.2(6) 90.1(6) 178.3(6) 178.0(6) 87.0(6) 135.2(6) 107.6(12) 106.5(12) 125.6(10) 106.4(12) 127.7(10) 124.5(10) 110.0(13) 127.3(10) 130.6(14) 111.2(13) 107.0(13) 108.2(13) 115.0(14) 130.3(13) 114(2) 104.3(12) 109(2) 106(2) 107(2) 115.2(13) 106.0(13) 114(2) 111(2) 105.4(14) 128.0(14) 113.8(14) 105.1(14) 107(2) 114.4(14) 111.2(14) 100.5(12) 104.8(12) 111.5(14) 110(2) 110.1(14) 112.3(12) F(2) -Sb(1) -F(4) F(6) -Sb(1) -F(5) F(1)-Sb(1)-F(S) F(6) -Sb(1) -F(3) F(1)-Sb(1)-F(3) F(5)-Sb(1)-F(3) F(18) -Sb(3) -F(15) F (18) -Sb (3) -F (16) F(15)-Sb(3)-F(16) F(14)-Sb(3)-F(17) F(16) -Sb(3) -F(17) F(14)-Sb(3)-F(13) F(16)-Sb(3)-F(13) F(20) -Sb(4) -F(21) F(21) -Sh(4) -F(23) F(21) -Sh(4) -F(22) F(20) -Sb(4) -F(24) F(23) -Sb(4) -F(24) F(20) -Sb(4) -F(19) F(23) -Sb(4) -F(19) F(24) -Sb(4) -F(19) C (1) -o(1) -C(7) C(1A)-O(1A)-C(7A) C(1)-N(1)-C(6) c(6) -N(1) -Cu(1) C(3) -N(2) -Cu(1) C(1A)-N(1A)-C(6A) C (6A) -N (1A) -Cu (2) C(3A)-N(2A)-Cu(2) N(1)-c(1)-o(1) 0(1)-C(1)-C(2) C(1) -C(2) -C(5) c(1) -C(2) -C(4) C(5)-C(2)-C(4) 0(2)-c(3)-c(2) C(8)-C(6)-N(1) N(1) -C(6) -C(7) C(9)-C(S)-C(6) c(6)-c(8)-c(11) c(6) -c(8) -c(10) c(13)-c(12)-n(2) N(2) -C(12) -C(14) c(17)-c(14)-c(16) C(16) -C(14) -C(12) C(16) -C(14) -C(15) N(1A) -C(1A) -0(1A) O(1A)-C(1A)-C(2A) C(3A)-C(2A)-C(4A) C(3A) -C(2A) -C(5A) C(4A) -C(2A) -C(5A) N(2A) -c(3a) -C(2A) N(1A)-C(6A)-C(8A) C(8A) -C(6A) -C(7A) C(11A)-C(8A)-C(1OA) C(1OA)-C(8A)-C(6A) C(10A)-C(8A)-C(9A) N(2A) -C(12A) -C(13A) C(13A)-C(12A)-C(14A) 165.4(11) 87.4(7) 90.7(12) 90.9(9) 90.7(13) 175.7(7) 94.2(6) 93.1(7) 92.8(6) 87.0(8) 87.5(8) 89.9(7) 89.4(6) 89.2(7) 90.0(7) 91.0(6) 93.2(7) 87.5(6) 90.5(8) 90.2(7) 91.9(6) 107.3(12) 107.9(12) 108.0(12) 126.1(10) 125.9(10) 108.2(12) 127.3(10) 122.6(11) 116.0(13) 112.6(14) 109.5(13) 109.1(14) 111.8(14) 114.6(13) 108.9(12) 101.6(13) 114(2) 114(2) 108(2) 100.6(13) 112.2(13) 109(2) 109.4(13) 107(2) 115.3(14) 116.6(13) 114(2) 109(2) 108.4(14) 134(2) 111.7(13) 115.4(14) 110(2) 108(2) 108(2) 103.4(12) 114.6(13)

10 vtw6 American onemicai zociety journai ui urganic enemistry voi rage oj4 nvans 3upplemental rage! J. Org. Chem. Supportig Information page S9 o(2a) -C(13A) -C(12A) C(15A) -C(14A) -C(16A) C(1SA)-C(14A)-C(12A) C(16A) -C(14A) -C(12A) Cl (4) -C(2S) -Cl (3) F(9) -Sb(2)-F(8) F(9) -Sb(2) -F(10) F(8) -Sb(2) -F(10) F(11) -Sb (2) -F(7) r(10) -Sb(2) -F(7) F(11) -Sb(2) -F(12) F(10) -Sb(2) -F(12) Sb(2) -F(7) -Cu(1) 102.1(11) 111(2) 106.9(14) 110.1(13) 104.4(13) 97.4(12) 100.0(14) 89.6(11) 84.7(13) 91.2(11) 93.7(13) 81.2(12) 131.9(8) c(15a) -C(14A) -C(17A) c(17a) -C(14A) -C(16A) c (17A) -C(14A) - C(12A) Cl(2)-c(1S)-Cl(1) F(9) -Sb(2) -F(11) F(11) -Sb(2) -F(8) F(11) -Sb(2) -F(10) F(9)-Sb(2)-F(7) F(8) -Sb(2) -F(7) F(9)-Sb(2)-F(12) F(8) -Sb(2) -F(12) F(7) -Sb(2) -F(12) 109.2(14) 108.7(14) 111.2(14) 94.7(13) 84.9(13) 94.0(14) 173.6(14) 88.8(11) 173.6(11) 175.3(10) 87.2(9) 86.6(9) Symmetry transformations used to generate equivalent atoms:

11 vtj6 American onemicai 3ociety joumai ui urganic enemistry voi rage odi nvans 3uppiemental rage iu J. Org. Chem. Supportig Information page SIO Table 4. Anisotropic displacement parameters EA2 x 10 3 for 1. The anisotropic displacement factor exponent takes the form: -2w2 [ (ha*) 2 u hka*b*U 2 Ull U22 U33 U23 U13 U12 Cu(1) 46(1) 27(1) 39(1) 1(1) 8(1) 4(1) Cu(2) 46(1) 29(1) 42(1) 3(1) 6(1)' 5(1) Sb (1) 82(1) 58(1) 56(1) -7(1) -9(1) 22(1) Sb(3) 61(1) 40(1) 60(1) 0(1) 9(1) 5(1) Sb(4) 51(1) 64(1) 40(1) 1(1) -11(1) 0(1) F(1) 461(43) 77(13) 271(30) -40(15) -170(30) -33(19) F (2) 142(15) 309(28) 138(15) 66(16) -54(12) 77(17) F(3) 289(23) 169(16) 54(8) 26(11) 53(11) 127(17) F(4) 198(17) 217(19) 65(9) 8(10) 17(10) 148(15) F(5) 85(8) 133(11) 88(8) -15(10) 10(7) 16(9) F(6) 320(28) 197(20) 259(24) -165(19) 216(23) -208(21) F(13) 92(8) 95(9) 77(8) -19(8) 16(6) -9(8) F(14) 125(12) 42(7) 231(20) 7(9) 79(13) 25(7) F (15) 145(11) 80(8) 87(8) -6(8) 54(8) 38(9) F(16) 152(13) 32(7) 191(17) -45(9) 73(12) -23(8) F(17) 63(8) 234(19) 120(11) 59(13) -4(7) -13(10) F(18) 88(8) 118(10) 106(9) -8(9) -30(7) 3(8) F(19) 59(7) 202(17) 95(9) 14(10) 12(6) 46(9) F (20) 183(17) 89(10) 146(14) -43(10) -40(13) -58(11) F(21) 68(8) 145(12) 111(10) -22(9) 9(7) 7(8) F(22) 129(10) 148(13) 52(7) 27(8) -27(7) -2(10) F(23) 161(13) 40(6) 86(9) -7(6) -17(9) -8(7) F (24) 105(9) 95(9) 66(7) 27(7) -20(7) 8(7) 0(1) 59(7) 60(8) 32(6) -11(6) 15(6) 3(6) 0(2) 70(8) 17(6) 66(8) 8(5) 19(7) 0(5) 0(3) 83(9) 37(6) 52(7) 10(6) -2(6) 26(6) O(4) 62(8) 55(7) 40(7) -12(6) 8(6) 10(6) 0(1A) 60(8) 53(8) 59(8) -9(6) 8(7) -4(6) 0(2A) 57(8) 39(7) 55(8) 15(6) -13(6) 0(6) 0(3A) 71(8) 44(7) 44(7) 3(5) -9(6) 30(6) 0(4A) 76(9) 50(7) 49(8) -6(6) 3(6) 20(6) N(1) 56(8) 38(8) 21(7) -5(6) 3(6) 2(7) N(2) 48(8) 34(8) 23(7) 16(6) 1(6) -3(6) N(1A) 32(7) 36(8) 48(8) 14(7) 10(6) 5(7) N(2A) 22(7) 29(7) 36(8) 3(6) 1(6) 0(6) C(1) 37(9) 49(11) 26(9) 6(8) 3(8) -8(8) C(2) 56(11) 32(9) 22(9) -5(7) 16(8) 3(7) C(3) 42(10) 29(9) 33(9) -3(7) -15(8) -10(7) C(4) 28(9) 89(15) 69(13) 10(11) -6(9) 10(9) C(5) 99(15) 23(9) 50(11) -12(8) 1(10) 4(9) C(6) 72(13) 48(11) 23(9) 17(8) 0(9) -5(9) C(7) 87(14) 60(12) 37(10) 19(9) 16(9) 7(11) C(8) 56(12) 47(11) 56(12) 10(9) 6(9) -13(9) C(9) 95(16) 35(10) 78(14) -27(10) 5(12) -22(10) C(10) 91(17) 57(13) 88(16) 11(12) 8(13) -17(12) C(11) 53(12) 54(12) 90(16) 4(11) -23(11) 0(9) C(12) 57(11) 33(9) 40(10) 6(8) -9(8) -19(8)

12 '"Mirlluall %-Illrlllllual 13uulrLy I~~~~~~~~~ Ji~il ULU I11l1Ld1 J'ilgalR 'k111d %-~11lLlj' U~~ V Uj rage UJ'-tI IA L ami OUppluh1r1Ld1 rage I I J. Org. Chem. Supportig Information page Sl 1 C (13) 41(10) 48(11) 59(12) 5(9) -9(9) -10(8) c (14) 48(11) 44(11) 64(12) 13(9) -1(9) -6(8) c (15) 61(14) 85(17) 87(17) 21(13) 14(12) -7(12) c(16) 38(10) 59(12) 85(14) 21(10) -11(9) 13(8) C (17) 87(15) 55(13) 76(15) -24(11) -19(12) 1(11) C (1A) 16(8) 45(10) 43(10) -6(8) 2(7) 11(7) C(2A) 43(11) 36(10) 83(15) 0(9) -6(10) 19(8) C(3A) 29 (9) 46(11) 41(10) 6(8) 3(8) -2(8) c (4A) 56(12) 51(11) 82(15) 25(10) -6(11) 12(9) c (5A) 85 (14) 42 (11) 65 (13) -33 (9) 12 (11) 6(10) C(6A) 50 (11) 53 (11) 33(10) 8(8) 11(8) -3(9) c (7A) 58(10) 32(9) 41(10) -4(8) 14(8) -19(8) c(8a) 60(11) 35(9) 43(10) -1(8) 0(9), -10 (8) C (9A) 85(15) 60(12) 50(12) -16 (9) 5(11) -23 (11) C (10A) 86(17) 65(14) 104(18) 7(13) 21(14) -26(13) C (11A) 47(11) 69(13) 78(15) 15(11) -22(10) -5(10) C(12A) 52(10) 41(9) 26(9) -2(7) 15(8) -8(8) C (13A) 65 (11) 40(10) 41(10) 22(8) 2(9) -11(9) c (14A) 46(10) 50(11) 40(10) 0(8) -2 (8) -18 (8) C(15A) 83(15) 70(14) 54(13) 15(11) 14(11) -30(12) C (16A) 35(10) 80(14) 74(13) 35(11) -5(9) -10(9) C (17A) 65(12) 50(11) 53(12) 11(9) -15(10) -25(10) c (is) 257(20) 50(12) 115(15) -2(11) 102(15) 16(14) Cl (1) 283(11) 83(5) 87(5) 1(4) -8(6) 49(6) Cl (2) 123 (6) 145 (7) 174 (8) 59(6) 2(6) 30(6) C (2S) 74(13) 140(16) 85(13) -10(12) -15(11) -6(12) cl (3) 267 (10) 77(4) 75(4) -17(3) -61(5) 33(5) c1(4) 95(4) 100(4) 97(4) 5(4) -20(3) 4(4) Sb (2) 68(1) 67(1) 50(1) -1(1) -19(1) -6(1) F (7) 211(19) 267(24) 95(12) -105(14) -66(12) 63(18) F (8) 139 (14) 385(32) 87(11) -111(16) -4(10) 37(18) F (9) 292 (28) 89(12) 465 (43) -82 (18) -279 (30) 81(15) F (10) 257 (26) 285 (30) 197 (21) 28(20) 41(19) -196 (24) F (11) 117 (16) 316 (34) 384 (40) 116(30) -7 (21) -116 (19) F (12) 161(17) 227(22) 261(25) -98(19) -166(18) 79(16)

13 viti American onemicai 3ociety joumai ui urganic enemistry voi rage odi nvans 3upplemental rage I/ J. Org. Chem. Supportig Information page S12 Table 5. Hydrogen coordinates ( x. 2 3 displacement parameters (A x 10 ) for ) and isotropic y z U(eq) H(3A) H{3B) H{4D) H(4E) H(3AA) H (3A3) H(4AA) H(4AB) H(4A) H(4B) H(4C) H(5A) H(5B) H(5C) H (6A) H(7A) H(7B) "(9A) H(9B) H(9C) H(10A) H (10B) H(1OC) H(11A) H (11B) H(11C) H(12A) H (13A) H (13B) H(15A) H(15B) H (15C) H(16A) H(16B) H(16C) H(17A) H (17B) H (17C) H(4F) H(4G) H(4H) H(5D) H(5E) H(5F) H(6B) H(7C) H(7D) "(9D) 5553(12) 5336(12) 6943(11) 5805(11) 10319(11) 9950(11) 11586(13) 10329(13) 9997(16) 10209(16) 10614(16) 8082(20) 8675(20) 7144(20) 7821(19) 8523(20) 10037(20) 9827(21) 8686(21) 8409(21) 10636(22) 10978(22) 9546(22) 11256(18) 10583(18) 11586(18) 5818(17) 7146(16) 5964(16) 3585(21) 3849(21) 2534(21) 3763(16) 2734(16) 4175(16) 4569(22) 4673(22) 3232(22) 15410(18) 14826(18) 15212(18) 13394(20) 11886(20) 12712(20) 12973(18) 13803(16) 15267(16) 13178(20) 8478(5) 8862(5) 7979(5) 8500(5) 8389(5) 8827(5) 7957(5) 8319(5) 5954(9) 6690(9) 6388(9) 5590(7) 6017(7) 6102(7) 8524(8) 7881(9) 8011(9) 9205(8) 8680(8) 9279(8) 8933(9) 9375(9) 9430(9) 7970(8) 7905(8) 8476(8) 6811(7) 5968(8) 5596(8) 6457(10) 5772(10) 6157(10) 7426(8) 7126(8) 7373(8) 5680(9) 6301(9) 6054(9) 6289(8) 5849(8) 6565(8) 6012(8) 6154(8) 5586(8) 8507(8) 7863M(7) 7975(7) 9210(9) 6946(7) 7650M(7) 9332(6) 9199(6) 1800(6) 2288(6) 4199M(7) 3912(7) 7771(12) 7926(12) 7100(12) 6803(10) 6117(10) 6363(10) 6346(9) 5353(10) 5682(10) 7999(12) 8087(12) 7532(12) 5969(13) 6714(13) 6258(13) 6874(13) 7717(13) 7553(13) 9285(10) 9392(11) 8918(11) 9618(13) 9266(13) 8989(13) 8749(11) 8107(11) 7844(11) 7790(13) 7261(13) 7524(13) 1983(12) 2659(12) 2852(12) 1063(11) 1317(11) 1720(11) 1320(10) 378(9) 791(9) 2531(11)

14 vi"6 American onemicai 3ociety journai ui urganic enemistry voi rage odj 4 nvans 3uppiemental rage 1- J. Org. Chem. Supportig Information page S13 "(9E) 14513(20) 9203 (9) 3086(11) 97 "(OF) 13477(20) 8628(9) 3109(11) 97 H(1OD) 14586(22) 9385(10) 1350(14) 127 H(10E) 15800(22) 8921(10) 1156(14) 127 H(10F) 15917(22) 9375(10) 1909(14) 127 " (11D) 15381(17) 7855(9) 2785(12) 98 H(11E) 16403(17) 8437(9) 2789(12) 98 H (11F) 16286(17) 7983(9) 2036(12) 98 H(12B) 10828(16) 6866(7) 4248(9) 47 H(13C) 12154(17) 6030(7) 4459(10) 59 H(13D) 10974(17) 5617(7) 4035(10) 59 "(15D) 8604(21) 6451(9) 4665(11) 103 s(15e) 8969(21) 5768(9) 4338(11).103 H(15F) 7581(21) 6096(9) 4067(11) 103 H(16D) 9006(16) 7304(9) 2821(11) 95 H(16E) 8614(16) 7407(9) 3722(11) 95 H(16F) 7597(16) 7049(9) 3124(11) 95 H(17D) 9559(19) 6214(8) 2326(11) 84 H(17E) 8163(19) 5951(8) 2638(11) 84 H(17F) 9551(19) 5622(8) 2910(11) 84 H(2S) 3008(33) 9621(11) 4843(15) 167 H(IS) 4276(33) 9303(11) 4929(15) 167 H(3S) -233(21) 10289(14) 9909(14) 120 H(4S) 266(21) 9569(14) 9883(14) 120

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