# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2011 data_global _journal_coden_Cambridge 182 _journal_volume ? _journal_page_first ? _journal_year ? loop_ _publ_author_name 'Rong, Lingling' 'Liu, Qiancai' 'Shi, Yingbo' 'Tang, Jie' _publ_contact_author_name 'Liu, Qiancai' _publ_contact_author_email qcliu@chem.ecnu.edu.cn _publ_section_title ; Fluoradenes via palladium-catalyzed intramolecular arylation ; # Attachment '- 4a.cif' data_z1 _database_code_depnum_ccdc_archive 'CCDC 801484' #TrackingRef '- 4a.cif' _audit_creation_method SHELXL-97 _audit_creation_date 2010-09-28 _audit_update_record 2010-09-28 _chemical_formula_sum 'C54 H29 N O2' _chemical_formula_weight 723.780 _refine_ls_R_factor_all 0.049 _cell_length_a 8.3866(3) _cell_length_b 28.4107(9) _cell_length_c 8.9081(4) _cell_angle_alpha 90.000 _cell_angle_beta 117.935(1) _cell_angle_gamma 90.000 _cell_volume 1875.2(1) _cell_formula_units_Z 2 _symmetry_int_tables_number 11 _symmetry_space_group_name_H-M 'P 1 21/m 1' _symmetry_space_group_name_Hall -P_2yb loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 x,y,z 2 -x,0.500+y,-z 3 -x,-y,-z 4 x,0.500-y,z loop_ _atom_type_symbol _atom_type_oxidation_number _atom_type_radius_bond N ? 1.200 H ? 1.200 C ? 1.200 O ? 1.200 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_Wyckoff_symbol _atom_site_attached_hydrogens _atom_site_calc_flag _atom_site_thermal_displace_type _atom_site_u_iso_or_equiv N1 N 0.0416(4) 0.2500 0.1027(3) 1.000 2 e ? d Uani 0.0498(6) H1A H 0.072(4) 0.2500 0.203(4) 1.000 2 e ? d Uiso 0.059(9) C1 C 0.2857(2) 0.0542(1) -0.2268(2) 1.000 4 f ? d Uani 0.0413(4) C2 C 0.4639(2) 0.0413(1) -0.1703(2) 1.000 4 f ? d Uani 0.0503(5) H2A H 0.5057 0.0125 -0.1159 1.000 4 f ? calc Uiso 0.06000 C3 C 0.5792(3) 0.0712(1) -0.1953(3) 1.000 4 f ? d Uani 0.0570(5) H3A H 0.6992 0.0626 -0.1560 1.000 4 f ? calc Uiso 0.06800 C4 C 0.5193(3) 0.1134(1) -0.2770(3) 1.000 4 f ? d Uani 0.0594(5) H4A H 0.5985 0.1329 -0.2939 1.000 4 f ? calc Uiso 0.07100 C5 C 0.3402(3) 0.1274(1) -0.3351(2) 1.000 4 f ? d Uani 0.0501(4) H5A H 0.3000 0.1561 -0.3898 1.000 4 f ? calc Uiso 0.06000 C6 C 0.2244(2) 0.0980(1) -0.3102(2) 1.000 4 f ? d Uani 0.0397(4) C7 C 0.0277(2) 0.1061(0) -0.3493(2) 1.000 4 f ? d Uani 0.0365(4) C8 C -0.0168(2) 0.0576(0) -0.3148(2) 1.000 4 f ? d Uani 0.0378(4) C9 C 0.1292(2) 0.0279(1) -0.2351(2) 1.000 4 f ? d Uani 0.0408(4) C10 C 0.0910(3) -0.0193(1) -0.2227(2) 1.000 4 f ? d Uani 0.0488(4) H10A H 0.1831 -0.0408 -0.1632 1.000 4 f ? calc Uiso 0.05900 C11 C -0.0891(3) -0.0334(1) -0.3019(2) 1.000 4 f ? d Uani 0.0509(5) H11A H -0.1168 -0.0640 -0.2840 1.000 4 f ? calc Uiso 0.06100 C12 C -0.2293(3) -0.0038(1) -0.4066(2) 1.000 4 f ? d Uani 0.0485(4) H12A H -0.3465 -0.0152 -0.4669 1.000 4 f ? calc Uiso 0.05800 C13 C -0.1908(2) 0.0433(1) -0.4193(2) 1.000 4 f ? d Uani 0.0409(4) C14 C -0.2703(2) 0.0805(1) -0.5511(2) 1.000 4 f ? d Uani 0.0425(4) C15 C -0.1339(2) 0.1140(1) -0.5251(2) 1.000 4 f ? d Uani 0.0395(4) C16 C -0.1613(3) 0.1472(1) -0.6469(2) 1.000 4 f ? d Uani 0.0488(4) H16A H -0.0714 0.1689 -0.6306 1.000 4 f ? calc Uiso 0.05900 C17 C -0.3257(3) 0.1480(1) -0.7950(2) 1.000 4 f ? d Uani 0.0611(5) H17A H -0.3441 0.1695 -0.8802 1.000 4 f ? calc Uiso 0.07300 C18 C -0.4613(3) 0.1172(1) -0.8166(3) 1.000 4 f ? d Uani 0.0641(6) H18A H -0.5721 0.1192 -0.9140 1.000 4 f ? calc Uiso 0.07700 C19 C -0.4357(3) 0.0831(1) -0.6957(2) 1.000 4 f ? d Uani 0.0543(5) H19A H -0.5282 0.0625 -0.7115 1.000 4 f ? calc Uiso 0.06500 C20 C 0.0264(2) 0.1435(0) -0.2235(2) 1.000 4 f ? d Uani 0.0354(4) C21 C 0.0393(2) 0.1303(1) -0.0668(2) 1.000 4 f ? d Uani 0.0407(4) H21A H 0.0440 0.0984 -0.0410 1.000 4 f ? calc Uiso 0.04900 C22 C 0.0453(3) 0.1629(1) 0.0509(2) 1.000 4 f ? d Uani 0.0468(4) H22A H 0.0535 0.1534 0.1541 1.000 4 f ? calc Uiso 0.05600 C23 C 0.0387(2) 0.2104(1) 0.0109(2) 1.000 4 f ? d Uani 0.0405(4) C24 C 0.0264(2) 0.2245(0) -0.1449(2) 1.000 4 f ? d Uani 0.0366(4) C25 C 0.0200(2) 0.1909(1) -0.2613(2) 1.000 4 f ? d Uani 0.0393(4) H25A H 0.0115 0.2003 -0.3648 1.000 4 f ? calc Uiso 0.04700 O01 O 0.253(3) 0.2500 0.514(3) 0.500 2 e ? d Uani 0.094(5) O02 O 0.546(5) 0.2305(10) 0.626(3) 0.250 4 f ? d Uani 0.076(5) C01 C 0.478(4) 0.2500 0.820(4) 0.500 2 e ? d Uani 0.085(6) C02 C 0.393(4) 0.2500 0.625(3) 0.500 2 e ? d Uani 0.062(3) C03 C 0.477(3) 0.2141(10) 0.410(3) 0.250 4 f ? d Uani 0.086(6) C04 C 0.559(3) 0.2500 0.375(2) 0.500 2 e ? d Uani 0.107(4) O01' O 0.2491(17) 0.2500 0.514(2) 0.500 2 e ? d Uani 0.054(3) C01' C 0.439(4) 0.2500 0.809(4) 0.500 2 e ? d Uani 0.075(6) C02' C 0.414(5) 0.2500 0.636(4) 0.500 2 e ? d Uani 0.085(5) O02' O 0.529(4) 0.2747(10) 0.598(3) 0.250 4 f ? d Uani 0.063(3) C03' C 0.517(3) 0.2845(9) 0.449(3) 0.250 4 f ? d Uani 0.066(4) C04' C 0.505(3) 0.2500 0.321(2) 0.500 2 e ? d Uani 0.115(5) loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 N1 0.0857(17) 0.0351(11) 0.0443(12) 0.00000 0.0434(12) 0.00000 C1 0.0426(9) 0.0413(9) 0.0385(8) -0.0001(7) 0.0177(7) -0.0080(7) C2 0.0467(10) 0.0548(11) 0.0448(10) 0.0090(8) 0.0176(8) -0.0060(8) C3 0.0408(10) 0.0747(14) 0.0552(11) 0.0017(9) 0.0222(9) -0.0115(10) C4 0.0499(11) 0.0701(13) 0.0673(13) -0.0112(10) 0.035(1) -0.0114(11) C5 0.0531(11) 0.0466(10) 0.0557(11) -0.0066(8) 0.0296(9) -0.0056(8) C6 0.0401(9) 0.0408(9) 0.0381(8) -0.0029(7) 0.0182(7) -0.0084(7) C7 0.0384(8) 0.0341(8) 0.0372(8) -0.0005(7) 0.0178(7) -0.0021(6) C8 0.0425(9) 0.0346(8) 0.0388(8) -0.0017(7) 0.0213(7) -0.0048(7) C9 0.0476(10) 0.0366(8) 0.0369(8) 0.0010(7) 0.0188(7) -0.0038(7) C10 0.0616(11) 0.0373(9) 0.0471(10) 0.0057(8) 0.0251(9) 0.0001(7) C11 0.0678(12) 0.0358(9) 0.0554(11) -0.0075(8) 0.0339(10) -0.0044(8) C12 0.0513(10) 0.0457(10) 0.0538(10) -0.0130(8) 0.0290(9) -0.0124(8) C13 0.0418(9) 0.0408(9) 0.0437(9) -0.0027(7) 0.0232(7) -0.0085(7) C14 0.0401(9) 0.0435(9) 0.0444(9) 0.0017(7) 0.0202(8) -0.0100(7) C15 0.0428(9) 0.0382(9) 0.0382(8) 0.0045(7) 0.0196(7) -0.0056(7) C16 0.0596(11) 0.0456(10) 0.0421(9) 0.0048(8) 0.0245(8) -0.0018(8) C17 0.0748(14) 0.0581(12) 0.0413(10) 0.0139(11) 0.0196(10) 0.0019(9) C18 0.0539(12) 0.0735(14) 0.045(1) 0.0186(11) 0.0065(9) -0.0093(10) C19 0.0418(10) 0.0595(12) 0.0537(11) 0.0029(9) 0.0157(9) -0.0140(9) C20 0.0337(8) 0.0333(8) 0.0389(8) -0.0018(6) 0.0168(7) -0.0024(6) C21 0.0489(10) 0.0319(8) 0.0452(9) -0.0010(7) 0.0253(8) 0.0022(7) C22 0.0683(12) 0.0387(9) 0.0441(9) -0.0021(8) 0.0352(9) 0.0041(7) C23 0.052(1) 0.0351(9) 0.0422(9) -0.0006(7) 0.0284(8) -0.0006(7) C24 0.0422(9) 0.0331(8) 0.0376(8) -0.0004(7) 0.0213(7) 0.0011(6) C25 0.0482(9) 0.0371(9) 0.0347(8) -0.0010(7) 0.0211(7) 0.0008(7) O01 0.098(9) 0.085(9) 0.071(9) 0.00000 0.016(7) 0.00000 O02 0.063(6) 0.072(8) 0.083(9) 0.000(6) 0.026(7) 0.013(7) C01 0.094(13) 0.097(9) 0.067(11) 0.00000 0.039(10) 0.00000 C02 0.067(7) 0.075(6) 0.055(5) 0.00000 0.037(6) 0.00000 C03 0.101(11) 0.076(8) 0.095(11) 0.023(8) 0.056(8) -0.009(7) C04 0.109(10) 0.129(7) 0.092(8) 0.00000 0.055(7) 0.00000 O01' 0.047(5) 0.056(6) 0.067(7) 0.00000 0.034(5) 0.00000 C01' 0.068(8) 0.080(7) 0.048(6) 0.00000 0.003(6) 0.00000 C02' 0.075(8) 0.074(6) 0.082(7) 0.00000 0.019(6) 0.00000 O02' 0.061(7) 0.062(6) 0.068(6) 0.000(5) 0.032(5) 0.009(4) C03' 0.068(7) 0.074(7) 0.068(8) 0.005(5) 0.041(6) -0.005(6) C04' 0.097(9) 0.120(7) 0.114(10) 0.00000 0.038(7) 0.00000 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag N1 C23 . . 1.386(2) no N1 C23 . 4 1.386(2) no N1 H1A . . 0.81(3) no C1 C2 . . 1.385(2) no C1 C6 . . 1.417(2) no C1 C9 . . 1.482(2) no C2 C3 . . 1.382(3) no C2 H2A . . 0.9300 no C3 C4 . . 1.369(3) no C3 H3A . . 0.9300 no C4 C5 . . 1.398(3) no C4 H4A . . 0.9300 no C5 C6 . . 1.374(2) no C5 H5A . . 0.9300 no C6 C7 . . 1.535(2) no C7 C8 . . 1.495(2) no C7 C15 . . 1.534(2) no C7 C20 . . 1.550(2) no C8 C13 . . 1.374(2) no C8 C9 . . 1.380(2) no C9 C10 . . 1.396(2) no C10 C11 . . 1.393(3) no C10 H10A . . 0.9300 no C11 C12 . . 1.391(3) no C11 H11A . . 0.9300 no C12 C13 . . 1.394(2) no C12 H12A . . 0.9300 no C13 C14 . . 1.484(2) no C14 C19 . . 1.384(2) no C14 C15 . . 1.422(2) no C15 C16 . . 1.373(2) no C16 C17 . . 1.392(3) no C16 H16A . . 0.9300 no C17 C18 . . 1.375(3) no C17 H17A . . 0.9300 no C18 C19 . . 1.387(3) no C18 H18A . . 0.9300 no C19 H19A . . 0.9300 no C20 C25 . . 1.382(2) no C20 C21 . . 1.400(2) no C21 C22 . . 1.384(2) no C21 H21A . . 0.9300 no C22 C23 . . 1.387(2) no C22 H22A . . 0.9300 no C23 C24 . . 1.402(2) no C24 C25 . . 1.392(2) no C24 C24 . 4 1.449(3) no C25 H25A . . 0.9300 no O01 C02 . . 1.12(4) no O02 O02 . 4 1.11(6) no O02 C02 . . 1.39(5) no O02 C03 . . 1.79(4) no C01 C02 . . 1.54(5) no C02 O02 . 4 1.39(5) no C03 C04 . . 1.35(3) no C04 C03 . 4 1.35(3) no O01' C02' . . 1.30(4) no C01' C02' . . 1.46(5) no C02' O02' . 4 1.35(5) no C02' O02' . . 1.35(5) no O02' C03' . . 1.31(4) no O02' O02' . 4 1.41(5) no C03' C04' . . 1.47(3) no C03' C03' . 4 1.96(5) no C04' C03' . 4 1.47(3) no loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_2 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C23 N1 C23 . . 4 108.79(19) no C23 N1 H1A . . . 124.3(4) no C23 N1 H1A 4 . . 124.3(4) no C2 C1 C6 . . . 119.30(16) no C2 C1 C9 . . . 131.52(17) no C6 C1 C9 . . . 108.80(14) no C3 C2 C1 . . . 119.66(18) no C3 C2 H2A . . . 120.20 no C1 C2 H2A . . . 120.20 no C4 C3 C2 . . . 120.96(18) no C4 C3 H3A . . . 119.50 no C2 C3 H3A . . . 119.50 no C3 C4 C5 . . . 120.56(19) no C3 C4 H4A . . . 119.70 no C5 C4 H4A . . . 119.70 no C6 C5 C4 . . . 119.07(18) no C6 C5 H5A . . . 120.50 no C4 C5 H5A . . . 120.50 no C5 C6 C1 . . . 120.45(16) no C5 C6 C7 . . . 129.70(16) no C1 C6 C7 . . . 109.71(14) no C8 C7 C15 . . . 99.14(13) no C8 C7 C6 . . . 99.29(13) no C15 C7 C6 . . . 126.53(13) no C8 C7 C20 . . . 113.40(13) no C15 C7 C20 . . . 109.57(12) no C6 C7 C20 . . . 108.02(12) no C13 C8 C9 . . . 124.90(15) no C13 C8 C7 . . . 114.92(15) no C9 C8 C7 . . . 115.05(14) no C8 C9 C10 . . . 116.65(16) no C8 C9 C1 . . . 105.50(14) no C10 C9 C1 . . . 135.44(16) no C11 C10 C9 . . . 118.11(17) no C11 C10 H10A . . . 120.90 no C9 C10 H10A . . . 120.90 no C12 C11 C10 . . . 122.72(17) no C12 C11 H11A . . . 118.60 no C10 C11 H11A . . . 118.60 no C11 C12 C13 . . . 118.75(17) no C11 C12 H12A . . . 120.60 no C13 C12 H12A . . . 120.60 no C8 C13 C12 . . . 116.22(16) no C8 C13 C14 . . . 105.45(14) no C12 C13 C14 . . . 135.36(16) no C19 C14 C15 . . . 119.60(17) no C19 C14 C13 . . . 131.16(17) no C15 C14 C13 . . . 108.58(14) no C16 C15 C14 . . . 120.53(16) no C16 C15 C7 . . . 130.41(16) no C14 C15 C7 . . . 109.04(14) no C15 C16 C17 . . . 118.93(19) no C15 C16 H16A . . . 120.50 no C17 C16 H16A . . . 120.50 no C18 C17 C16 . . . 120.64(19) no C18 C17 H17A . . . 119.70 no C16 C17 H17A . . . 119.70 no C17 C18 C19 . . . 121.22(18) no C17 C18 H18A . . . 119.40 no C19 C18 H18A . . . 119.40 no C14 C19 C18 . . . 118.93(19) no C14 C19 H19A . . . 120.50 no C18 C19 H19A . . . 120.50 no C25 C20 C21 . . . 118.78(14) no C25 C20 C7 . . . 120.35(14) no C21 C20 C7 . . . 120.81(14) no C22 C21 C20 . . . 122.20(15) no C22 C21 H21A . . . 118.90 no C20 C21 H21A . . . 118.90 no C21 C22 C23 . . . 118.31(15) no C21 C22 H22A . . . 120.80 no C23 C22 H22A . . . 120.80 no N1 C23 C22 . . . 130.57(16) no N1 C23 C24 . . . 108.91(15) no C22 C23 C24 . . . 120.52(15) no C25 C24 C23 . . . 120.04(14) no C25 C24 C24 . . 4 133.29(9) no C23 C24 C24 . . 4 106.66(9) no C20 C25 C24 . . . 120.15(15) no C20 C25 H25A . . . 119.90 no C24 C25 H25A . . . 119.90 no O02 O02 C02 4 . . 66.5(13) no O02 O02 C03 4 . . 105.1(13) no C02 O02 C03 . . . 105.(2) no O01 C02 O02 . . 4 126.(2) no O01 C02 O02 . . . 126.(2) no O02 C02 O02 4 . . 47.(3) no O01 C02 C01 . . . 137.(2) no O02 C02 C01 4 . . 93.(3) no O02 C02 C01 . . . 93.(3) no C04 C03 O02 . . . 96.(2) no C03 C04 C03 . . 4 99.(3) no O01' C02' O02' . . 4 113.(2) no O01' C02' O02' . . . 113.(2) no O02' C02' O02' 4 . . 63.(3) no O01' C02' C01' . . . 117.(3) no O02' C02' C01' 4 . . 120.(3) no O02' C02' C01' . . . 120.(3) no C03' O02' C02' . . . 129.(3) no C03' O02' O02' . . 4 102.2(17) no C02' O02' O02' . . 4 58.7(15) no O02' C03' C04' . . . 126.(2) no O02' C03' C03' . . 4 77.8(17) no C04' C03' C03' . . 4 48.3(13) no C03' C04' C03' . . 4 83.(3) no loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion _geom_torsion_publ_flag C6 C1 C2 C3 . . . . 0.3(2) no C9 C1 C2 C3 . . . . 172.34(17) no C1 C2 C3 C4 . . . . -0.8(3) no C2 C3 C4 C5 . . . . 0.9(3) no C3 C4 C5 C6 . . . . -0.5(3) no C4 C5 C6 C1 . . . . 0.0(3) no C4 C5 C6 C7 . . . . 175.21(17) no C2 C1 C6 C5 . . . . 0.0(2) no C9 C1 C6 C5 . . . . -173.63(15) no C2 C1 C6 C7 . . . . -176.02(14) no C9 C1 C6 C7 . . . . 10.30(17) no C5 C6 C7 C8 . . . . 171.76(17) no C1 C6 C7 C8 . . . . -12.65(16) no C5 C6 C7 C15 . . . . 63.0(2) no C1 C6 C7 C15 . . . . -121.40(16) no C5 C6 C7 C20 . . . . -69.8(2) no C1 C6 C7 C20 . . . . 105.80(15) no C15 C7 C8 C13 . . . . -14.96(17) no C6 C7 C8 C13 . . . . -144.55(14) no C20 C7 C8 C13 . . . . 101.10(16) no C15 C7 C8 C9 . . . . 141.01(14) no C6 C7 C8 C9 . . . . 11.43(17) no C20 C7 C8 C9 . . . . -102.93(16) no C13 C8 C9 C10 . . . . -17.9(3) no C7 C8 C9 C10 . . . . -171.10(14) no C13 C8 C9 C1 . . . . 147.26(16) no C7 C8 C9 C1 . . . . -5.98(18) no C2 C1 C9 C8 . . . . -175.56(17) no C6 C1 C9 C8 . . . . -2.93(17) no C2 C1 C9 C10 . . . . -14.7(3) no C6 C1 C9 C10 . . . . 157.98(19) no C8 C9 C10 C11 . . . . 4.7(2) no C1 C9 C10 C11 . . . . -154.63(18) no C9 C10 C11 C12 . . . . 6.9(3) no C10 C11 C12 C13 . . . . -6.8(3) no C9 C8 C13 C12 . . . . 18.0(2) no C7 C8 C13 C12 . . . . 171.27(14) no C9 C8 C13 C14 . . . . -145.57(16) no C7 C8 C13 C14 . . . . 7.70(18) no C11 C12 C13 C8 . . . . -5.1(2) no C11 C12 C13 C14 . . . . 152.06(19) no C8 C13 C14 C19 . . . . 174.38(18) no C12 C13 C14 C19 . . . . 15.6(3) no C8 C13 C14 C15 . . . . 3.98(17) no C12 C13 C14 C15 . . . . -154.84(19) no C19 C14 C15 C16 . . . . -3.8(2) no C13 C14 C15 C16 . . . . 167.84(15) no C19 C14 C15 C7 . . . . 174.74(15) no C13 C14 C15 C7 . . . . -13.57(17) no C8 C7 C15 C16 . . . . -165.03(17) no C6 C7 C15 C16 . . . . -56.2(3) no C20 C7 C15 C16 . . . . 76.0(2) no C8 C7 C15 C14 . . . . 16.57(16) no C6 C7 C15 C14 . . . . 125.40(17) no C20 C7 C15 C14 . . . . -102.38(15) no C14 C15 C16 C17 . . . . 0.9(3) no C7 C15 C16 C17 . . . . -177.30(16) no C15 C16 C17 C18 . . . . 2.5(3) no C16 C17 C18 C19 . . . . -3.0(3) no C15 C14 C19 C18 . . . . 3.3(3) no C13 C14 C19 C18 . . . . -166.21(18) no C17 C18 C19 C14 . . . . 0.1(3) no C8 C7 C20 C25 . . . . -163.87(15) no C15 C7 C20 C25 . . . . -54.14(19) no C6 C7 C20 C25 . . . . 87.12(18) no C8 C7 C20 C21 . . . . 18.9(2) no C15 C7 C20 C21 . . . . 128.58(16) no C6 C7 C20 C21 . . . . -90.16(17) no C25 C20 C21 C22 . . . . 0.2(3) no C7 C20 C21 C22 . . . . 177.54(16) no C20 C21 C22 C23 . . . . -0.2(3) no C23 N1 C23 C22 4 . . . 177.83(13) no C23 N1 C23 C24 4 . . . -2.4(3) no C21 C22 C23 N1 . . . . 179.7(2) no C21 C22 C23 C24 . . . . 0.0(3) no N1 C23 C24 C25 . . . . -179.59(17) no C22 C23 C24 C25 . . . . 0.2(3) no N1 C23 C24 C24 . . . 4 1.46(17) no C22 C23 C24 C24 . . . 4 -178.75(14) no C21 C20 C25 C24 . . . . 0.0(2) no C7 C20 C25 C24 . . . . -177.35(14) no C23 C24 C25 C20 . . . . -0.2(2) no C24 C24 C25 C20 4 . . . 178.43(10) no O02 O02 C02 O01 4 . . . 108.3(17) no C03 O02 C02 O01 . . . . 8.(3) no C03 O02 C02 O02 . . . 4 -100.2(17) no O02 O02 C02 C01 4 . . . -91.4(11) no C03 O02 C02 C01 . . . . 168.4(18) no O02 O02 C03 C04 4 . . . 35.0(18) no C02 O02 C03 C04 . . . . 104.(2) no O02 C03 C04 C03 . . . 4 -58.(3) no O01' C02' O02' C03' . . . . -25.(4) no O02' C02' O02' C03' 4 . . . 80.(4) no C01' C02' O02' C03' . . . . -170.(3) no O01' C02' O02' O02' . . . 4 -105.(2) no C01' C02' O02' O02' . . . 4 110.(3) no C02' O02' C03' C04' . . . . -59.(5) no O02' O02' C03' C04' 4 . . . 1.(3) no C02' O02' C03' C03' . . . 4 -59.(3) no O02' O02' C03' C03' 4 . . 4 0.00(1) no O02' C03' C04' C03' . . . 4 -1.(4) no # Attachment '- 4ba.cif' data_z2 _database_code_depnum_ccdc_archive 'CCDC 801485' #TrackingRef '- 4ba.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C37 H31 N' _chemical_formula_weight 489.63 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 28.2705(10) _cell_length_b 12.8474(5) _cell_length_c 15.7041(6) _cell_angle_alpha 90.00 _cell_angle_beta 112.2090(10) _cell_angle_gamma 90.00 _cell_volume 5280.6(3) _cell_formula_units_Z 8 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.46 _exptl_crystal_size_mid 0.44 _exptl_crystal_size_min 0.32 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.232 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2080 _exptl_absorpt_coefficient_mu 0.070 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9684 _exptl_absorpt_correction_T_max 0.9778 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 30006 _diffrn_reflns_av_R_equivalents 0.0283 _diffrn_reflns_av_sigmaI/netI 0.0189 _diffrn_reflns_limit_h_min -33 _diffrn_reflns_limit_h_max 33 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.77 _diffrn_reflns_theta_max 25.01 _reflns_number_total 4640 _reflns_number_gt 3660 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0973P)^2^+16.8115P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4640 _refine_ls_number_parameters 343 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0987 _refine_ls_R_factor_gt 0.0808 _refine_ls_wR_factor_ref 0.2323 _refine_ls_wR_factor_gt 0.2111 _refine_ls_goodness_of_fit_ref 1.045 _refine_ls_restrained_S_all 1.045 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N1 N -0.00058(11) 0.3339(2) -0.0522(2) 0.0542(8) Uani 1 1 d . . . C1 C 0.14233(11) 0.7962(3) -0.0044(2) 0.0417(7) Uani 1 1 d . . . C2 C 0.12660(13) 0.8962(3) 0.0055(2) 0.0492(8) Uani 1 1 d . . . H2A H 0.1395 0.9297 0.0637 0.059 Uiso 1 1 calc R . . C3 C 0.09191(14) 0.9466(3) -0.0703(3) 0.0581(10) Uani 1 1 d . . . H3A H 0.0806 1.0147 -0.0640 0.070 Uiso 1 1 calc R . . C4 C 0.07354(14) 0.8977(3) -0.1558(3) 0.0599(10) Uani 1 1 d . . . H4A H 0.0510 0.9343 -0.2079 0.072 Uiso 1 1 calc R . . C5 C 0.08771(13) 0.7960(3) -0.1662(2) 0.0520(9) Uani 1 1 d . . . H5A H 0.0742 0.7625 -0.2244 0.062 Uiso 1 1 calc R . . C6 C 0.12164(12) 0.7447(3) -0.0906(2) 0.0433(7) Uani 1 1 d . . . C7 C 0.14192(12) 0.6329(2) -0.0796(2) 0.0412(7) Uani 1 1 d . . . C8 C 0.18572(11) 0.6438(2) 0.01085(19) 0.0376(7) Uani 1 1 d . . . C9 C 0.18495(11) 0.7331(2) 0.0588(2) 0.0401(7) Uani 1 1 d . . . C10 C 0.22917(13) 0.7554(3) 0.1356(2) 0.0442(8) Uani 1 1 d . . . H10A H 0.2302 0.8128 0.1745 0.053 Uiso 1 1 calc R . . C11 C 0.27113(12) 0.6920(3) 0.1533(2) 0.0460(8) Uani 1 1 d . . . H11A H 0.3001 0.7035 0.2082 0.055 Uiso 1 1 calc R . . C12 C 0.27325(12) 0.6119(3) 0.0950(2) 0.0456(8) Uani 1 1 d . . . H12A H 0.3039 0.5739 0.1067 0.055 Uiso 1 1 calc R . . C13 C 0.22890(12) 0.5891(2) 0.0190(2) 0.0409(7) Uani 1 1 d . . . C14 C 0.21815(13) 0.5427(2) -0.0729(2) 0.0441(8) Uani 1 1 d . . . C15 C 0.17017(13) 0.5790(2) -0.1341(2) 0.0451(8) Uani 1 1 d . . . C16 C 0.15395(16) 0.5567(3) -0.2272(2) 0.0579(10) Uani 1 1 d . . . H16A H 0.1217 0.5803 -0.2691 0.069 Uiso 1 1 calc R . . C17 C 0.1864(2) 0.4984(3) -0.2576(3) 0.0731(13) Uani 1 1 d . . . H17A H 0.1763 0.4841 -0.3214 0.088 Uiso 1 1 calc R . . C18 C 0.23256(19) 0.4613(3) -0.1974(3) 0.0693(12) Uani 1 1 d . . . H18A H 0.2533 0.4206 -0.2201 0.083 Uiso 1 1 calc R . . C19 C 0.24905(15) 0.4826(3) -0.1045(3) 0.0576(10) Uani 1 1 d . . . H19A H 0.2809 0.4566 -0.0630 0.069 Uiso 1 1 calc R . . C20 C 0.02126(15) 0.1681(3) 0.0395(3) 0.0567(9) Uani 1 1 d . . . H20A H -0.0130 0.1451 0.0231 0.068 Uiso 1 1 calc R . . C21 C 0.06107(17) 0.1106(3) 0.0962(3) 0.0618(10) Uani 1 1 d . . . H21A H 0.0543 0.0462 0.1193 0.074 Uiso 1 1 calc R . . C22 C 0.11156(16) 0.1434(3) 0.1215(3) 0.0591(9) Uani 1 1 d . . . H22A H 0.1385 0.1015 0.1615 0.071 Uiso 1 1 calc R . . C23 C 0.12279(14) 0.2361(3) 0.0890(2) 0.0510(8) Uani 1 1 d . . . H23A H 0.1572 0.2582 0.1062 0.061 Uiso 1 1 calc R . . C24 C 0.08311(12) 0.2968(3) 0.0309(2) 0.0440(8) Uani 1 1 d . . . C25 C 0.03215(13) 0.2621(3) 0.0061(2) 0.0479(8) Uani 1 1 d . . . C26 C 0.02814(12) 0.4145(3) -0.0669(2) 0.0484(8) Uani 1 1 d . . . C27 C 0.08027(12) 0.3948(2) -0.0166(2) 0.0414(7) Uani 1 1 d . . . C28 C 0.11662(12) 0.4657(2) -0.0211(2) 0.0415(7) Uani 1 1 d . . . H28A H 0.1520 0.4529 0.0119 0.050 Uiso 1 1 calc R . . C29 C 0.10096(12) 0.5553(3) -0.0739(2) 0.0430(7) Uani 1 1 d . . . C30 C 0.04897(13) 0.5726(3) -0.1229(2) 0.0559(9) Uani 1 1 d . . . H30A H 0.0385 0.6339 -0.1591 0.067 Uiso 1 1 calc R . . C31 C 0.01212(13) 0.5027(3) -0.1204(3) 0.0608(10) Uani 1 1 d . . . H31A H -0.0231 0.5151 -0.1545 0.073 Uiso 1 1 calc R . . C32 C -0.05527(15) 0.3230(4) -0.0984(4) 0.0853(15) Uani 1 1 d . . . H32A H -0.0717 0.3924 -0.1095 0.102 Uiso 1 1 calc R . . H32B H -0.0692 0.2821 -0.0598 0.102 Uiso 1 1 calc R . . C33 C -0.0669(2) 0.2625(8) -0.1975(6) 0.170(4) Uani 1 1 d . . . H33A H -0.0501 0.3012 -0.2329 0.204 Uiso 1 1 calc R . . H33B H -0.0516 0.1921 -0.1850 0.204 Uiso 1 1 calc R . . C34 C -0.1194(3) 0.2533(7) -0.2515(6) 0.150(3) Uani 1 1 d . . . H34A H -0.1344 0.3234 -0.2690 0.179 Uiso 1 1 calc R . . H34B H -0.1369 0.2187 -0.2153 0.179 Uiso 1 1 calc R . . C35 C -0.1271(5) 0.1913(7) -0.3362(6) 0.192(5) Uani 1 1 d . . . H35A H -0.1218 0.1163 -0.3212 0.230 Uiso 1 1 calc R . . H35B H -0.1027 0.2136 -0.3642 0.230 Uiso 1 1 calc R . . C36 C -0.1822(3) 0.2114(9) -0.4025(6) 0.149(3) Uani 1 1 d . . . H36A H -0.1856 0.2870 -0.4154 0.179 Uiso 1 1 calc R . . H36B H -0.1869 0.1760 -0.4612 0.179 Uiso 1 1 calc R . . C37 C -0.2259(3) 0.1794(6) -0.3758(5) 0.141(3) Uani 1 1 d . . . H37A H -0.2583 0.1983 -0.4250 0.212 Uiso 1 1 calc R . . H37B H -0.2230 0.2151 -0.3189 0.212 Uiso 1 1 calc R . . H37C H -0.2248 0.1039 -0.3660 0.212 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.0418(15) 0.0576(18) 0.0679(19) -0.0050(15) 0.0260(14) -0.0202(13) C1 0.0421(16) 0.0474(18) 0.0435(17) -0.0015(14) 0.0251(14) -0.0145(14) C2 0.0525(19) 0.0494(19) 0.058(2) -0.0040(16) 0.0355(17) -0.0142(15) C3 0.055(2) 0.054(2) 0.079(3) 0.0068(19) 0.040(2) -0.0045(17) C4 0.048(2) 0.063(2) 0.070(2) 0.0163(19) 0.0239(18) -0.0049(17) C5 0.0470(18) 0.060(2) 0.0485(19) 0.0067(16) 0.0177(15) -0.0151(16) C6 0.0437(17) 0.0474(18) 0.0439(17) -0.0009(14) 0.0224(14) -0.0166(14) C7 0.0431(16) 0.0470(17) 0.0357(15) -0.0037(13) 0.0174(13) -0.0157(14) C8 0.0415(16) 0.0438(16) 0.0341(15) -0.0034(12) 0.0217(13) -0.0169(13) C9 0.0463(17) 0.0458(17) 0.0376(16) -0.0050(13) 0.0263(14) -0.0179(14) C10 0.0564(19) 0.0476(17) 0.0343(15) -0.0062(13) 0.0236(14) -0.0219(15) C11 0.0465(18) 0.0552(19) 0.0360(16) 0.0018(14) 0.0154(14) -0.0204(15) C12 0.0426(17) 0.0499(18) 0.0479(18) 0.0046(15) 0.0212(14) -0.0134(14) C13 0.0454(17) 0.0422(16) 0.0423(16) -0.0016(13) 0.0249(14) -0.0153(13) C14 0.0530(18) 0.0422(17) 0.0469(18) -0.0046(14) 0.0299(15) -0.0177(14) C15 0.061(2) 0.0415(17) 0.0403(16) -0.0080(14) 0.0277(15) -0.0233(15) C16 0.078(2) 0.056(2) 0.0420(18) -0.0098(16) 0.0262(18) -0.0288(19) C17 0.117(4) 0.068(3) 0.056(2) -0.027(2) 0.057(3) -0.042(3) C18 0.097(3) 0.059(2) 0.077(3) -0.022(2) 0.060(3) -0.022(2) C19 0.072(2) 0.0464(19) 0.072(2) -0.0116(17) 0.048(2) -0.0182(17) C20 0.064(2) 0.058(2) 0.062(2) -0.0095(18) 0.0393(19) -0.0241(18) C21 0.088(3) 0.052(2) 0.059(2) -0.0059(18) 0.044(2) -0.025(2) C22 0.077(3) 0.051(2) 0.051(2) -0.0010(16) 0.0272(19) -0.0119(18) C23 0.055(2) 0.053(2) 0.0482(19) -0.0058(16) 0.0228(16) -0.0148(16) C24 0.0502(18) 0.0488(18) 0.0408(16) -0.0099(14) 0.0262(14) -0.0177(15) C25 0.0531(19) 0.0518(19) 0.0502(19) -0.0106(15) 0.0322(16) -0.0184(16) C26 0.0442(18) 0.0538(19) 0.0512(19) -0.0078(16) 0.0225(15) -0.0186(15) C27 0.0423(16) 0.0472(17) 0.0382(16) -0.0079(13) 0.0190(13) -0.0150(14) C28 0.0394(16) 0.0486(18) 0.0386(16) -0.0070(14) 0.0169(13) -0.0147(13) C29 0.0446(17) 0.0497(18) 0.0356(16) -0.0055(14) 0.0159(13) -0.0179(14) C30 0.0473(19) 0.058(2) 0.054(2) 0.0062(17) 0.0097(16) -0.0153(16) C31 0.0393(18) 0.065(2) 0.068(2) 0.0051(19) 0.0089(16) -0.0159(16) C32 0.047(2) 0.090(3) 0.114(4) 0.007(3) 0.025(2) -0.030(2) C33 0.075(4) 0.226(10) 0.174(8) -0.051(7) 0.008(4) -0.069(5) C34 0.163(7) 0.151(7) 0.147(7) -0.012(6) 0.072(6) -0.011(6) C35 0.376(18) 0.124(6) 0.118(6) -0.033(5) 0.144(9) 0.001(8) C36 0.133(6) 0.202(9) 0.111(6) -0.032(6) 0.044(5) -0.009(6) C37 0.186(8) 0.131(6) 0.129(6) -0.038(5) 0.085(6) -0.012(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C25 1.381(5) . ? N1 C26 1.388(4) . ? N1 C32 1.445(5) . ? C1 C2 1.386(5) . ? C1 C6 1.419(4) . ? C1 C9 1.480(5) . ? C2 C3 1.384(5) . ? C2 H2A 0.9500 . ? C3 C4 1.392(6) . ? C3 H3A 0.9500 . ? C4 C5 1.395(5) . ? C4 H4A 0.9500 . ? C5 C6 1.380(5) . ? C5 H5A 0.9500 . ? C6 C7 1.532(5) . ? C7 C8 1.497(4) . ? C7 C15 1.539(4) . ? C7 C29 1.556(4) . ? C8 C13 1.371(4) . ? C8 C9 1.377(4) . ? C9 C10 1.400(4) . ? C10 C11 1.378(5) . ? C10 H10A 0.9500 . ? C11 C12 1.394(5) . ? C11 H11A 0.9500 . ? C12 C13 1.397(4) . ? C12 H12A 0.9500 . ? C13 C14 1.483(4) . ? C14 C19 1.391(5) . ? C14 C15 1.412(5) . ? C15 C16 1.387(5) . ? C16 C17 1.401(6) . ? C16 H16A 0.9500 . ? C17 C18 1.374(7) . ? C17 H17A 0.9500 . ? C18 C19 1.381(6) . ? C18 H18A 0.9500 . ? C19 H19A 0.9500 . ? C20 C21 1.360(6) . ? C20 C25 1.396(5) . ? C20 H20A 0.9500 . ? C21 C22 1.395(6) . ? C21 H21A 0.9500 . ? C22 C23 1.380(5) . ? C22 H22A 0.9500 . ? C23 C24 1.387(5) . ? C23 H23A 0.9500 . ? C24 C25 1.415(4) . ? C24 C27 1.451(5) . ? C26 C31 1.381(5) . ? C26 C27 1.407(5) . ? C27 C28 1.395(4) . ? C28 C29 1.390(5) . ? C28 H28A 0.9500 . ? C29 C30 1.395(5) . ? C30 C31 1.388(5) . ? C30 H30A 0.9500 . ? C31 H31A 0.9500 . ? C32 C33 1.658(10) . ? C32 H32A 0.9900 . ? C32 H32B 0.9900 . ? C33 C34 1.408(9) . ? C33 H33A 0.9900 . ? C33 H33B 0.9900 . ? C34 C35 1.495(10) . ? C34 H34A 0.9900 . ? C34 H34B 0.9900 . ? C35 C36 1.534(13) . ? C35 H35A 0.9900 . ? C35 H35B 0.9900 . ? C36 C37 1.504(10) . ? C36 H36A 0.9900 . ? C36 H36B 0.9900 . ? C37 H37A 0.9800 . ? C37 H37B 0.9800 . ? C37 H37C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C25 N1 C26 108.8(3) . . ? C25 N1 C32 126.1(3) . . ? C26 N1 C32 124.9(3) . . ? C2 C1 C6 120.3(3) . . ? C2 C1 C9 130.3(3) . . ? C6 C1 C9 108.7(3) . . ? C3 C2 C1 119.3(3) . . ? C3 C2 H2A 120.3 . . ? C1 C2 H2A 120.3 . . ? C2 C3 C4 120.2(4) . . ? C2 C3 H3A 119.9 . . ? C4 C3 H3A 119.9 . . ? C3 C4 C5 121.1(4) . . ? C3 C4 H4A 119.5 . . ? C5 C4 H4A 119.5 . . ? C6 C5 C4 118.9(3) . . ? C6 C5 H5A 120.5 . . ? C4 C5 H5A 120.5 . . ? C5 C6 C1 120.0(3) . . ? C5 C6 C7 130.8(3) . . ? C1 C6 C7 109.2(3) . . ? C8 C7 C6 99.2(2) . . ? C8 C7 C15 98.8(2) . . ? C6 C7 C15 127.7(3) . . ? C8 C7 C29 111.8(2) . . ? C6 C7 C29 110.6(3) . . ? C15 C7 C29 107.3(2) . . ? C13 C8 C9 124.9(3) . . ? C13 C8 C7 115.4(3) . . ? C9 C8 C7 114.7(3) . . ? C8 C9 C10 116.7(3) . . ? C8 C9 C1 105.5(3) . . ? C10 C9 C1 134.5(3) . . ? C11 C10 C9 118.2(3) . . ? C11 C10 H10A 120.9 . . ? C9 C10 H10A 120.9 . . ? C10 C11 C12 123.5(3) . . ? C10 C11 H11A 118.3 . . ? C12 C11 H11A 118.3 . . ? C11 C12 C13 117.9(3) . . ? C11 C12 H12A 121.0 . . ? C13 C12 H12A 121.0 . . ? C8 C13 C12 116.9(3) . . ? C8 C13 C14 105.5(3) . . ? C12 C13 C14 134.7(3) . . ? C19 C14 C15 120.8(3) . . ? C19 C14 C13 130.2(3) . . ? C15 C14 C13 108.7(3) . . ? C16 C15 C14 119.9(3) . . ? C16 C15 C7 130.2(3) . . ? C14 C15 C7 109.7(3) . . ? C15 C16 C17 118.1(4) . . ? C15 C16 H16A 120.9 . . ? C17 C16 H16A 120.9 . . ? C18 C17 C16 121.7(4) . . ? C18 C17 H17A 119.2 . . ? C16 C17 H17A 119.2 . . ? C17 C18 C19 120.8(4) . . ? C17 C18 H18A 119.6 . . ? C19 C18 H18A 119.6 . . ? C18 C19 C14 118.7(4) . . ? C18 C19 H19A 120.7 . . ? C14 C19 H19A 120.7 . . ? C21 C20 C25 118.1(3) . . ? C21 C20 H20A 121.0 . . ? C25 C20 H20A 121.0 . . ? C20 C21 C22 121.8(3) . . ? C20 C21 H21A 119.1 . . ? C22 C21 H21A 119.1 . . ? C23 C22 C21 120.7(4) . . ? C23 C22 H22A 119.7 . . ? C21 C22 H22A 119.7 . . ? C22 C23 C24 119.1(3) . . ? C22 C23 H23A 120.4 . . ? C24 C23 H23A 120.4 . . ? C23 C24 C25 119.3(3) . . ? C23 C24 C27 134.4(3) . . ? C25 C24 C27 106.2(3) . . ? N1 C25 C20 129.8(3) . . ? N1 C25 C24 109.2(3) . . ? C20 C25 C24 121.0(4) . . ? C31 C26 N1 129.4(3) . . ? C31 C26 C27 121.5(3) . . ? N1 C26 C27 109.1(3) . . ? C28 C27 C26 119.3(3) . . ? C28 C27 C24 134.0(3) . . ? C26 C27 C24 106.7(3) . . ? C29 C28 C27 119.8(3) . . ? C29 C28 H28A 120.1 . . ? C27 C28 H28A 120.1 . . ? C28 C29 C30 119.5(3) . . ? C28 C29 C7 119.3(3) . . ? C30 C29 C7 121.2(3) . . ? C31 C30 C29 121.8(3) . . ? C31 C30 H30A 119.1 . . ? C29 C30 H30A 119.1 . . ? C26 C31 C30 118.1(3) . . ? C26 C31 H31A 120.9 . . ? C30 C31 H31A 120.9 . . ? N1 C32 C33 108.1(4) . . ? N1 C32 H32A 110.1 . . ? C33 C32 H32A 110.1 . . ? N1 C32 H32B 110.1 . . ? C33 C32 H32B 110.1 . . ? H32A C32 H32B 108.4 . . ? C34 C33 C32 113.2(7) . . ? C34 C33 H33A 108.9 . . ? C32 C33 H33A 108.9 . . ? C34 C33 H33B 108.9 . . ? C32 C33 H33B 108.9 . . ? H33A C33 H33B 107.7 . . ? C33 C34 C35 110.3(9) . . ? C33 C34 H34A 109.6 . . ? C35 C34 H34A 109.6 . . ? C33 C34 H34B 109.6 . . ? C35 C34 H34B 109.6 . . ? H34A C34 H34B 108.1 . . ? C34 C35 C36 106.5(9) . . ? C34 C35 H35A 110.4 . . ? C36 C35 H35A 110.4 . . ? C34 C35 H35B 110.4 . . ? C36 C35 H35B 110.4 . . ? H35A C35 H35B 108.6 . . ? C37 C36 C35 119.7(8) . . ? C37 C36 H36A 107.4 . . ? C35 C36 H36A 107.4 . . ? C37 C36 H36B 107.4 . . ? C35 C36 H36B 107.4 . . ? H36A C36 H36B 106.9 . . ? C36 C37 H37A 109.5 . . ? C36 C37 H37B 109.5 . . ? H37A C37 H37B 109.5 . . ? C36 C37 H37C 109.5 . . ? H37A C37 H37C 109.5 . . ? H37B C37 H37C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C1 C2 C3 -2.4(4) . . . . ? C9 C1 C2 C3 167.3(3) . . . . ? C1 C2 C3 C4 -0.7(5) . . . . ? C2 C3 C4 C5 2.9(5) . . . . ? C3 C4 C5 C6 -1.8(5) . . . . ? C4 C5 C6 C1 -1.3(4) . . . . ? C4 C5 C6 C7 176.5(3) . . . . ? C2 C1 C6 C5 3.4(4) . . . . ? C9 C1 C6 C5 -168.3(3) . . . . ? C2 C1 C6 C7 -174.9(3) . . . . ? C9 C1 C6 C7 13.4(3) . . . . ? C5 C6 C7 C8 165.9(3) . . . . ? C1 C6 C7 C8 -16.1(3) . . . . ? C5 C6 C7 C15 57.2(5) . . . . ? C1 C6 C7 C15 -124.8(3) . . . . ? C5 C6 C7 C29 -76.5(4) . . . . ? C1 C6 C7 C29 101.5(3) . . . . ? C6 C7 C8 C13 -142.1(3) . . . . ? C15 C7 C8 C13 -11.5(3) . . . . ? C29 C7 C8 C13 101.2(3) . . . . ? C6 C7 C8 C9 14.3(3) . . . . ? C15 C7 C8 C9 144.9(2) . . . . ? C29 C7 C8 C9 -102.4(3) . . . . ? C13 C8 C9 C10 -15.6(4) . . . . ? C7 C8 C9 C10 -169.4(2) . . . . ? C13 C8 C9 C1 146.7(3) . . . . ? C7 C8 C9 C1 -7.1(3) . . . . ? C2 C1 C9 C8 -174.8(3) . . . . ? C6 C1 C9 C8 -4.2(3) . . . . ? C2 C1 C9 C10 -17.2(5) . . . . ? C6 C1 C9 C10 153.4(3) . . . . ? C8 C9 C10 C11 5.0(4) . . . . ? C1 C9 C10 C11 -150.8(3) . . . . ? C9 C10 C11 C12 5.2(4) . . . . ? C10 C11 C12 C13 -5.8(4) . . . . ? C9 C8 C13 C12 15.0(4) . . . . ? C7 C8 C13 C12 168.6(3) . . . . ? C9 C8 C13 C14 -148.6(3) . . . . ? C7 C8 C13 C14 5.0(3) . . . . ? C11 C12 C13 C8 -3.8(4) . . . . ? C11 C12 C13 C14 153.7(3) . . . . ? C8 C13 C14 C19 177.8(3) . . . . ? C12 C13 C14 C19 18.5(6) . . . . ? C8 C13 C14 C15 4.6(3) . . . . ? C12 C13 C14 C15 -154.6(3) . . . . ? C19 C14 C15 C16 -1.5(4) . . . . ? C13 C14 C15 C16 172.4(3) . . . . ? C19 C14 C15 C7 174.0(3) . . . . ? C13 C14 C15 C7 -12.1(3) . . . . ? C8 C7 C15 C16 -171.3(3) . . . . ? C6 C7 C15 C16 -62.5(5) . . . . ? C29 C7 C15 C16 72.5(4) . . . . ? C8 C7 C15 C14 13.8(3) . . . . ? C6 C7 C15 C14 122.6(3) . . . . ? C29 C7 C15 C14 -102.4(3) . . . . ? C14 C15 C16 C17 -0.2(5) . . . . ? C7 C15 C16 C17 -174.7(3) . . . . ? C15 C16 C17 C18 1.7(5) . . . . ? C16 C17 C18 C19 -1.5(6) . . . . ? C17 C18 C19 C14 -0.3(5) . . . . ? C15 C14 C19 C18 1.8(5) . . . . ? C13 C14 C19 C18 -170.6(3) . . . . ? C25 C20 C21 C22 0.4(5) . . . . ? C20 C21 C22 C23 -0.3(6) . . . . ? C21 C22 C23 C24 0.2(5) . . . . ? C22 C23 C24 C25 -0.2(5) . . . . ? C22 C23 C24 C27 -178.8(3) . . . . ? C26 N1 C25 C20 -179.1(3) . . . . ? C32 N1 C25 C20 -5.0(6) . . . . ? C26 N1 C25 C24 0.7(4) . . . . ? C32 N1 C25 C24 174.8(4) . . . . ? C21 C20 C25 N1 179.5(3) . . . . ? C21 C20 C25 C24 -0.4(5) . . . . ? C23 C24 C25 N1 -179.6(3) . . . . ? C27 C24 C25 N1 -0.6(4) . . . . ? C23 C24 C25 C20 0.3(5) . . . . ? C27 C24 C25 C20 179.2(3) . . . . ? C25 N1 C26 C31 179.5(4) . . . . ? C32 N1 C26 C31 5.3(6) . . . . ? C25 N1 C26 C27 -0.5(4) . . . . ? C32 N1 C26 C27 -174.7(4) . . . . ? C31 C26 C27 C28 -0.2(5) . . . . ? N1 C26 C27 C28 179.8(3) . . . . ? C31 C26 C27 C24 -179.9(3) . . . . ? N1 C26 C27 C24 0.1(4) . . . . ? C23 C24 C27 C28 -0.6(6) . . . . ? C25 C24 C27 C28 -179.4(3) . . . . ? C23 C24 C27 C26 179.1(4) . . . . ? C25 C24 C27 C26 0.3(3) . . . . ? C26 C27 C28 C29 0.8(4) . . . . ? C24 C27 C28 C29 -179.5(3) . . . . ? C27 C28 C29 C30 -0.8(5) . . . . ? C27 C28 C29 C7 -179.0(3) . . . . ? C8 C7 C29 C28 -38.5(4) . . . . ? C6 C7 C29 C28 -148.0(3) . . . . ? C15 C7 C29 C28 68.8(3) . . . . ? C8 C7 C29 C30 143.4(3) . . . . ? C6 C7 C29 C30 33.8(4) . . . . ? C15 C7 C29 C30 -109.4(4) . . . . ? C28 C29 C30 C31 0.2(5) . . . . ? C7 C29 C30 C31 178.3(3) . . . . ? N1 C26 C31 C30 179.5(4) . . . . ? C27 C26 C31 C30 -0.5(6) . . . . ? C29 C30 C31 C26 0.5(6) . . . . ? C25 N1 C32 C33 -87.9(6) . . . . ? C26 N1 C32 C33 85.4(6) . . . . ? N1 C32 C33 C34 -176.2(7) . . . . ? C32 C33 C34 C35 -175.8(7) . . . . ? C33 C34 C35 C36 -164.1(9) . . . . ? C34 C35 C36 C37 -62.5(11) . . . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 25.01 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.737 _refine_diff_density_min -0.545 _refine_diff_density_rms 0.061 # Attachment '- 4bb.cif' data_z3 _database_code_depnum_ccdc_archive 'CCDC 801486' #TrackingRef '- 4bb.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C56 H41 N' _chemical_formula_weight 727.90 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 13.3928(5) _cell_length_b 15.7368(5) _cell_length_c 19.3999(7) _cell_angle_alpha 90.00 _cell_angle_beta 107.3490(10) _cell_angle_gamma 90.00 _cell_volume 3902.7(2) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.48 _exptl_crystal_size_mid 0.36 _exptl_crystal_size_min 0.22 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.239 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1536 _exptl_absorpt_coefficient_mu 0.071 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9669 _exptl_absorpt_correction_T_max 0.9846 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 44922 _diffrn_reflns_av_R_equivalents 0.0493 _diffrn_reflns_av_sigmaI/netI 0.0330 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 1.59 _diffrn_reflns_theta_max 25.01 _reflns_number_total 6868 _reflns_number_gt 4957 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0813P)^2^+2.9465P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6868 _refine_ls_number_parameters 514 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0855 _refine_ls_R_factor_gt 0.0594 _refine_ls_wR_factor_ref 0.1749 _refine_ls_wR_factor_gt 0.1526 _refine_ls_goodness_of_fit_ref 1.029 _refine_ls_restrained_S_all 1.029 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N1 N 0.45058(15) 0.11493(12) 0.45575(10) 0.0327(5) Uani 1 1 d . . . C1 C 0.8669(2) 0.1056(2) 0.72515(14) 0.0460(7) Uani 1 1 d . . . C2 C 0.8428(2) 0.1616(3) 0.77257(15) 0.0645(9) Uani 1 1 d . . . H2A H 0.8294 0.2197 0.7597 0.077 Uiso 1 1 calc R . . C3 C 0.8383(3) 0.1328(4) 0.83857(18) 0.0859(14) Uani 1 1 d . . . H3A H 0.8237 0.1716 0.8718 0.103 Uiso 1 1 calc R . . C4 C 0.8548(3) 0.0490(4) 0.85680(19) 0.0949(16) Uani 1 1 d . . . H4A H 0.8480 0.0301 0.9017 0.114 Uiso 1 1 calc R . . C5 C 0.8811(3) -0.0091(3) 0.81160(19) 0.0817(12) Uani 1 1 d . . . H5A H 0.8930 -0.0671 0.8251 0.098 Uiso 1 1 calc R . . C6 C 0.8896(2) 0.0199(2) 0.74556(15) 0.0560(8) Uani 1 1 d . . . C7 C 0.9313(2) -0.02177(19) 0.69124(16) 0.0561(8) Uani 1 1 d . . . C8 C 0.9243(2) 0.03822(17) 0.63875(14) 0.0438(6) Uani 1 1 d . . . C9 C 0.86612(19) 0.11708(16) 0.64605(13) 0.0371(6) Uani 1 1 d . . . C10 C 0.9240(2) 0.18185(18) 0.61303(14) 0.0449(7) Uani 1 1 d . . . C11 C 0.9867(2) 0.1372(2) 0.57721(14) 0.0518(8) Uani 1 1 d . . . C12 C 0.9907(2) 0.0469(2) 0.59760(15) 0.0521(8) Uani 1 1 d . . . C13 C 1.0570(3) -0.0237(3) 0.59788(19) 0.0750(11) Uani 1 1 d . . . H13A H 1.1032 -0.0242 0.5690 0.090 Uiso 1 1 calc R . . C14 C 1.0516(3) -0.0918(3) 0.6421(2) 0.0849(13) Uani 1 1 d . . . H14A H 1.0892 -0.1419 0.6384 0.102 Uiso 1 1 calc R . . C15 C 0.9957(3) -0.0915(2) 0.6908(2) 0.0789(11) Uani 1 1 d . . . H15A H 1.0005 -0.1374 0.7234 0.095 Uiso 1 1 calc R . . C16 C 1.0325(3) 0.1802(3) 0.53225(17) 0.0725(11) Uani 1 1 d . . . H16A H 1.0751 0.1508 0.5087 0.087 Uiso 1 1 calc R . . C17 C 1.0159(3) 0.2651(3) 0.5222(2) 0.0836(13) Uani 1 1 d . . . H17A H 1.0455 0.2942 0.4901 0.100 Uiso 1 1 calc R . . C18 C 0.9575(3) 0.3101(3) 0.5571(2) 0.0825(12) Uani 1 1 d . . . H18A H 0.9495 0.3698 0.5504 0.099 Uiso 1 1 calc R . . C19 C 0.9090(2) 0.2677(2) 0.60317(18) 0.0601(8) Uani 1 1 d . . . H19A H 0.8671 0.2981 0.6266 0.072 Uiso 1 1 calc R . . C20 C 0.6035(2) -0.03067(15) 0.21009(13) 0.0369(6) Uani 1 1 d . . . C21 C 0.6916(2) 0.01978(17) 0.23378(14) 0.0453(7) Uani 1 1 d . . . H21A H 0.7404 0.0109 0.2801 0.054 Uiso 1 1 calc R . . C22 C 0.7076(3) 0.08354(19) 0.18888(16) 0.0585(8) Uani 1 1 d . . . H22A H 0.7688 0.1177 0.2042 0.070 Uiso 1 1 calc R . . C23 C 0.6365(3) 0.09802(19) 0.12276(16) 0.0605(9) Uani 1 1 d . . . H23A H 0.6484 0.1429 0.0934 0.073 Uiso 1 1 calc R . . C24 C 0.5470(3) 0.04816(17) 0.09773(14) 0.0508(7) Uani 1 1 d . . . H24A H 0.4983 0.0584 0.0517 0.061 Uiso 1 1 calc R . . C25 C 0.5307(2) -0.01702(16) 0.14179(13) 0.0404(6) Uani 1 1 d . . . C26 C 0.4487(2) -0.08357(16) 0.12856(13) 0.0394(6) Uani 1 1 d . . . C27 C 0.47132(19) -0.12988(15) 0.19164(12) 0.0338(5) Uani 1 1 d . . . C28 C 0.55949(19) -0.09659(14) 0.25187(12) 0.0320(5) Uani 1 1 d . . . C29 C 0.60769(19) -0.18118(15) 0.28531(12) 0.0335(5) Uani 1 1 d . . . C30 C 0.5340(2) -0.24757(15) 0.25853(13) 0.0353(6) Uani 1 1 d . . . C31 C 0.45002(19) -0.21518(15) 0.19578(13) 0.0351(6) Uani 1 1 d . . . C32 C 0.3806(2) -0.25216(18) 0.13485(14) 0.0432(6) Uani 1 1 d . . . H32A H 0.3595 -0.3097 0.1354 0.052 Uiso 1 1 calc R . . C33 C 0.3430(2) -0.20245(19) 0.07306(14) 0.0487(7) Uani 1 1 d . . . H33A H 0.2910 -0.2256 0.0329 0.058 Uiso 1 1 calc R . . C34 C 0.3786(2) -0.12006(18) 0.06779(14) 0.0459(7) Uani 1 1 d . . . H34A H 0.3555 -0.0895 0.0237 0.055 Uiso 1 1 calc R . . C35 C 0.5539(2) -0.32903(16) 0.28562(15) 0.0454(7) Uani 1 1 d . . . H35A H 0.5040 -0.3729 0.2686 0.055 Uiso 1 1 calc R . . C36 C 0.6470(2) -0.34574(18) 0.33762(16) 0.0544(8) Uani 1 1 d . . . H36A H 0.6610 -0.4015 0.3568 0.065 Uiso 1 1 calc R . . C37 C 0.7204(2) -0.28248(18) 0.36225(16) 0.0541(8) Uani 1 1 d . . . H37A H 0.7851 -0.2957 0.3971 0.065 Uiso 1 1 calc R . . C38 C 0.7011(2) -0.19946(17) 0.33676(14) 0.0418(6) Uani 1 1 d . . . H38A H 0.7515 -0.1561 0.3546 0.050 Uiso 1 1 calc R . . C39 C 0.46167(18) 0.06155(14) 0.40176(12) 0.0299(5) Uani 1 1 d . . . C40 C 0.38764(19) 0.03456(15) 0.33922(12) 0.0344(5) Uani 1 1 d . . . H40A H 0.3168 0.0522 0.3281 0.041 Uiso 1 1 calc R . . C41 C 0.41986(19) -0.01860(15) 0.29357(12) 0.0332(5) Uani 1 1 d . . . H41A H 0.3698 -0.0381 0.2507 0.040 Uiso 1 1 calc R . . C43 C 0.52406(18) -0.04487(14) 0.30824(12) 0.0299(5) Uani 1 1 d . . . C44 C 0.59726(18) -0.01852(14) 0.37164(12) 0.0295(5) Uani 1 1 d . . . H44A H 0.6679 -0.0368 0.3826 0.035 Uiso 1 1 calc R . . C45 C 0.56701(18) 0.03480(14) 0.41905(12) 0.0288(5) Uani 1 1 d . . . C46 C 0.62136(18) 0.07456(14) 0.48731(11) 0.0280(5) Uani 1 1 d . . . C47 C 0.54627(18) 0.12384(14) 0.50709(12) 0.0302(5) Uani 1 1 d . . . C48 C 0.57350(19) 0.17131(15) 0.57035(12) 0.0334(5) Uani 1 1 d . . . H48A H 0.5234 0.2055 0.5832 0.040 Uiso 1 1 calc R . . C49 C 0.6755(2) 0.16717(15) 0.61373(13) 0.0360(6) Uani 1 1 d . . . H49A H 0.6950 0.1992 0.6572 0.043 Uiso 1 1 calc R . . C50 C 0.75185(19) 0.11764(15) 0.59656(12) 0.0332(5) Uani 1 1 d . . . C51 C 0.72334(18) 0.07187(15) 0.53230(12) 0.0312(5) Uani 1 1 d . . . H51A H 0.7741 0.0386 0.5192 0.037 Uiso 1 1 calc R . . C52 C 0.3546(2) 0.15744(17) 0.45525(15) 0.0419(6) Uani 1 1 d . . . H52A H 0.3566 0.1706 0.5055 0.050 Uiso 1 1 calc R . . H52B H 0.2949 0.1187 0.4347 0.050 Uiso 1 1 calc R . . C53 C 0.3377(3) 0.2383(2) 0.4120(2) 0.0708(10) Uani 1 1 d . . . H53A H 0.3320 0.2253 0.3611 0.085 Uiso 1 1 calc R . . H53B H 0.3984 0.2765 0.4312 0.085 Uiso 1 1 calc R . . C54 C 0.2384(3) 0.2825(3) 0.4159(2) 0.0889(13) Uani 1 1 d . . . H54A H 0.1778 0.2444 0.3959 0.107 Uiso 1 1 calc R . . H54B H 0.2437 0.2941 0.4670 0.107 Uiso 1 1 calc R . . C55 C 0.2208(4) 0.3654(3) 0.3739(3) 0.1169(18) Uani 1 1 d . . . H55A H 0.2849 0.4004 0.3906 0.140 Uiso 1 1 calc R . . H55B H 0.2093 0.3526 0.3221 0.140 Uiso 1 1 calc R . . C56 C 0.1327(4) 0.4148(3) 0.3810(3) 0.0978(14) Uani 1 1 d . . . H56A H 0.0709 0.3770 0.3710 0.117 Uiso 1 1 calc R . . H56B H 0.1167 0.4596 0.3435 0.117 Uiso 1 1 calc R . . C57 C 0.1476(4) 0.4564(3) 0.4533(3) 0.1044(15) Uani 1 1 d . . . H57A H 0.0837 0.4871 0.4529 0.157 Uiso 1 1 calc R . . H57B H 0.2063 0.4964 0.4630 0.157 Uiso 1 1 calc R . . H57C H 0.1624 0.4128 0.4911 0.157 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.0298(11) 0.0345(11) 0.0329(10) -0.0032(8) 0.0082(9) 0.0013(9) C1 0.0310(14) 0.0716(19) 0.0307(13) -0.0032(13) 0.0020(11) -0.0048(13) C2 0.0396(17) 0.116(3) 0.0340(15) -0.0169(16) 0.0052(13) 0.0066(17) C3 0.049(2) 0.170(5) 0.0358(18) -0.005(2) 0.0072(15) 0.013(3) C4 0.050(2) 0.197(6) 0.0341(18) 0.014(3) 0.0068(16) -0.017(3) C5 0.056(2) 0.120(3) 0.052(2) 0.031(2) -0.0085(17) -0.016(2) C6 0.0408(17) 0.078(2) 0.0385(15) 0.0073(15) -0.0039(13) -0.0110(15) C7 0.0485(18) 0.0501(17) 0.0505(17) 0.0017(14) -0.0146(14) 0.0000(14) C8 0.0386(15) 0.0500(16) 0.0347(13) -0.0108(12) -0.0012(12) 0.0021(12) C9 0.0341(14) 0.0450(14) 0.0299(12) -0.0068(11) 0.0059(11) -0.0014(11) C10 0.0383(15) 0.0549(17) 0.0357(14) -0.0051(12) 0.0022(12) -0.0093(12) C11 0.0333(15) 0.085(2) 0.0335(14) -0.0060(14) 0.0048(12) -0.0107(14) C12 0.0383(16) 0.073(2) 0.0382(15) -0.0148(14) 0.0004(12) 0.0084(14) C13 0.055(2) 0.106(3) 0.0532(19) -0.030(2) -0.0010(16) 0.023(2) C14 0.084(3) 0.078(3) 0.066(2) -0.018(2) -0.019(2) 0.037(2) C15 0.082(3) 0.062(2) 0.066(2) -0.0010(18) -0.018(2) 0.0108(19) C16 0.051(2) 0.117(3) 0.0467(18) 0.0007(19) 0.0097(15) -0.023(2) C17 0.058(2) 0.120(4) 0.065(2) 0.019(2) 0.0065(19) -0.036(2) C18 0.069(3) 0.068(2) 0.088(3) 0.019(2) -0.010(2) -0.030(2) C19 0.0484(18) 0.0567(19) 0.0631(19) -0.0008(15) -0.0020(15) -0.0142(15) C20 0.0510(16) 0.0327(13) 0.0317(13) -0.0048(10) 0.0196(12) 0.0002(11) C21 0.0589(18) 0.0433(15) 0.0374(14) -0.0067(12) 0.0201(13) -0.0116(13) C22 0.086(2) 0.0506(17) 0.0473(17) -0.0087(14) 0.0324(17) -0.0212(16) C23 0.103(3) 0.0400(16) 0.0479(17) -0.0020(13) 0.0376(18) -0.0145(17) C24 0.083(2) 0.0421(15) 0.0320(14) 0.0028(11) 0.0233(14) 0.0073(15) C25 0.0568(17) 0.0349(13) 0.0325(13) -0.0032(11) 0.0179(12) 0.0041(12) C26 0.0488(16) 0.0410(14) 0.0284(12) -0.0026(10) 0.0115(11) 0.0109(12) C27 0.0364(14) 0.0339(13) 0.0297(12) -0.0053(10) 0.0079(10) 0.0026(10) C28 0.0360(14) 0.0321(12) 0.0274(12) -0.0029(9) 0.0087(10) -0.0012(10) C29 0.0388(14) 0.0319(12) 0.0299(12) -0.0034(10) 0.0104(11) 0.0012(10) C30 0.0395(14) 0.0331(13) 0.0340(13) -0.0043(10) 0.0119(11) -0.0003(11) C31 0.0363(14) 0.0354(13) 0.0330(12) -0.0066(10) 0.0093(11) 0.0001(11) C32 0.0407(15) 0.0435(15) 0.0437(15) -0.0150(12) 0.0100(12) -0.0025(12) C33 0.0404(16) 0.0647(19) 0.0356(14) -0.0181(13) 0.0029(12) 0.0017(14) C34 0.0499(17) 0.0569(17) 0.0278(13) -0.0050(12) 0.0069(12) 0.0110(14) C35 0.0541(18) 0.0332(14) 0.0466(15) -0.0036(11) 0.0112(14) -0.0035(12) C36 0.064(2) 0.0339(14) 0.0572(18) 0.0042(13) 0.0062(15) 0.0099(14) C37 0.0489(18) 0.0486(17) 0.0528(17) 0.0010(14) -0.0030(14) 0.0129(14) C38 0.0381(15) 0.0410(14) 0.0412(14) -0.0065(11) 0.0043(12) -0.0002(12) C39 0.0328(13) 0.0292(12) 0.0284(11) 0.0013(9) 0.0102(10) -0.0003(10) C40 0.0312(13) 0.0351(13) 0.0357(13) 0.0017(10) 0.0081(11) 0.0011(10) C41 0.0361(14) 0.0323(12) 0.0276(11) -0.0001(10) 0.0040(10) -0.0041(10) C43 0.0366(14) 0.0261(11) 0.0267(11) 0.0011(9) 0.0088(10) -0.0016(10) C44 0.0289(13) 0.0307(12) 0.0282(11) 0.0029(9) 0.0075(10) -0.0003(10) C45 0.0318(13) 0.0290(12) 0.0259(11) 0.0036(9) 0.0090(10) -0.0020(10) C46 0.0322(13) 0.0277(11) 0.0247(11) 0.0006(9) 0.0093(10) -0.0022(10) C47 0.0329(13) 0.0304(12) 0.0277(11) 0.0019(9) 0.0098(10) -0.0014(10) C48 0.0373(15) 0.0313(12) 0.0334(13) -0.0034(10) 0.0131(11) 0.0018(10) C49 0.0440(16) 0.0346(13) 0.0292(12) -0.0058(10) 0.0108(11) -0.0036(11) C50 0.0358(14) 0.0352(13) 0.0274(12) -0.0021(10) 0.0078(10) -0.0037(11) C51 0.0338(14) 0.0338(12) 0.0277(11) -0.0005(10) 0.0117(10) -0.0003(10) C52 0.0355(15) 0.0434(15) 0.0473(15) -0.0075(12) 0.0131(12) 0.0055(12) C53 0.063(2) 0.0552(19) 0.093(3) 0.0104(18) 0.0219(19) 0.0161(17) C54 0.089(3) 0.086(3) 0.099(3) 0.022(2) 0.039(2) 0.036(2) C55 0.097(4) 0.113(4) 0.152(5) 0.047(3) 0.054(3) 0.029(3) C56 0.086(3) 0.073(3) 0.134(4) 0.014(3) 0.032(3) 0.013(2) C57 0.109(4) 0.070(3) 0.124(4) -0.018(3) 0.019(3) -0.007(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C47 1.376(3) . ? N1 C39 1.385(3) . ? N1 C52 1.447(3) . ? C1 C2 1.380(4) . ? C1 C6 1.413(4) . ? C1 C9 1.542(3) . ? C2 C3 1.376(5) . ? C2 H2A 0.9500 . ? C3 C4 1.367(7) . ? C3 H3A 0.9500 . ? C4 C5 1.383(6) . ? C4 H4A 0.9500 . ? C5 C6 1.396(4) . ? C5 H5A 0.9500 . ? C6 C7 1.485(4) . ? C7 C8 1.371(4) . ? C7 C15 1.397(5) . ? C8 C12 1.368(4) . ? C8 C9 1.494(4) . ? C9 C10 1.532(4) . ? C9 C50 1.545(3) . ? C10 C19 1.371(4) . ? C10 C11 1.424(4) . ? C11 C16 1.384(4) . ? C11 C12 1.472(4) . ? C12 C13 1.421(4) . ? C13 C14 1.389(6) . ? C13 H13A 0.9500 . ? C14 C15 1.370(6) . ? C14 H14A 0.9500 . ? C15 H15A 0.9500 . ? C16 C17 1.359(6) . ? C16 H16A 0.9500 . ? C17 C18 1.375(6) . ? C17 H17A 0.9500 . ? C18 C19 1.418(5) . ? C18 H18A 0.9500 . ? C19 H19A 0.9500 . ? C20 C21 1.382(4) . ? C20 C25 1.408(4) . ? C20 C28 1.538(3) . ? C21 C22 1.387(4) . ? C21 H21A 0.9500 . ? C22 C23 1.370(5) . ? C22 H22A 0.9500 . ? C23 C24 1.393(4) . ? C23 H23A 0.9500 . ? C24 C25 1.394(4) . ? C24 H24A 0.9500 . ? C25 C26 1.483(4) . ? C26 C27 1.378(3) . ? C26 C34 1.393(4) . ? C27 C31 1.380(3) . ? C27 C28 1.487(3) . ? C28 C29 1.536(3) . ? C28 C43 1.547(3) . ? C29 C38 1.378(4) . ? C29 C30 1.424(3) . ? C30 C35 1.381(4) . ? C30 C31 1.480(3) . ? C31 C32 1.395(3) . ? C32 C33 1.394(4) . ? C32 H32A 0.9500 . ? C33 C34 1.396(4) . ? C33 H33A 0.9500 . ? C34 H34A 0.9500 . ? C35 C36 1.375(4) . ? C35 H35A 0.9500 . ? C36 C37 1.380(4) . ? C36 H36A 0.9500 . ? C37 C38 1.394(4) . ? C37 H37A 0.9500 . ? C38 H38A 0.9500 . ? C39 C40 1.385(3) . ? C39 C45 1.413(3) . ? C40 C41 1.378(3) . ? C40 H40A 0.9500 . ? C41 C43 1.401(3) . ? C41 H41A 0.9500 . ? C43 C44 1.388(3) . ? C44 C45 1.391(3) . ? C44 H44A 0.9500 . ? C45 C46 1.449(3) . ? C46 C51 1.385(3) . ? C46 C47 1.411(3) . ? C47 C48 1.389(3) . ? C48 C49 1.376(4) . ? C48 H48A 0.9500 . ? C49 C50 1.403(3) . ? C49 H49A 0.9500 . ? C50 C51 1.391(3) . ? C51 H51A 0.9500 . ? C52 C53 1.503(4) . ? C52 H52A 0.9900 . ? C52 H52B 0.9900 . ? C53 C54 1.522(5) . ? C53 H53A 0.9900 . ? C53 H53B 0.9900 . ? C54 C55 1.520(6) . ? C54 H54A 0.9900 . ? C54 H54B 0.9900 . ? C55 C56 1.454(6) . ? C55 H55A 0.9900 . ? C55 H55B 0.9900 . ? C56 C57 1.505(6) . ? C56 H56A 0.9900 . ? C56 H56B 0.9900 . ? C57 H57A 0.9800 . ? C57 H57B 0.9800 . ? C57 H57C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C47 N1 C39 108.82(18) . . ? C47 N1 C52 126.3(2) . . ? C39 N1 C52 124.8(2) . . ? C2 C1 C6 119.8(3) . . ? C2 C1 C9 130.9(3) . . ? C6 C1 C9 109.2(2) . . ? C3 C2 C1 119.6(4) . . ? C3 C2 H2A 120.2 . . ? C1 C2 H2A 120.2 . . ? C4 C3 C2 120.7(4) . . ? C4 C3 H3A 119.7 . . ? C2 C3 H3A 119.7 . . ? C3 C4 C5 121.7(4) . . ? C3 C4 H4A 119.1 . . ? C5 C4 H4A 119.1 . . ? C4 C5 C6 118.1(4) . . ? C4 C5 H5A 120.9 . . ? C6 C5 H5A 120.9 . . ? C5 C6 C1 120.0(3) . . ? C5 C6 C7 131.1(3) . . ? C1 C6 C7 108.5(2) . . ? C8 C7 C15 116.2(3) . . ? C8 C7 C6 105.4(3) . . ? C15 C7 C6 135.6(3) . . ? C12 C8 C7 126.1(3) . . ? C12 C8 C9 114.9(3) . . ? C7 C8 C9 115.1(2) . . ? C8 C9 C10 99.8(2) . . ? C8 C9 C1 98.5(2) . . ? C10 C9 C1 129.8(2) . . ? C8 C9 C50 113.2(2) . . ? C10 C9 C50 105.5(2) . . ? C1 C9 C50 109.3(2) . . ? C19 C10 C11 120.1(3) . . ? C19 C10 C9 130.0(3) . . ? C11 C10 C9 108.7(2) . . ? C16 C11 C10 120.2(3) . . ? C16 C11 C12 130.9(3) . . ? C10 C11 C12 109.0(2) . . ? C8 C12 C13 115.8(3) . . ? C8 C12 C11 105.9(2) . . ? C13 C12 C11 136.8(3) . . ? C14 C13 C12 117.3(3) . . ? C14 C13 H13A 121.4 . . ? C12 C13 H13A 121.4 . . ? C15 C14 C13 124.3(3) . . ? C15 C14 H14A 117.9 . . ? C13 C14 H14A 117.9 . . ? C14 C15 C7 118.2(4) . . ? C14 C15 H15A 120.9 . . ? C7 C15 H15A 120.9 . . ? C17 C16 C11 119.2(4) . . ? C17 C16 H16A 120.4 . . ? C11 C16 H16A 120.4 . . ? C16 C17 C18 121.9(4) . . ? C16 C17 H17A 119.1 . . ? C18 C17 H17A 119.1 . . ? C17 C18 C19 120.2(4) . . ? C17 C18 H18A 119.9 . . ? C19 C18 H18A 119.9 . . ? C10 C19 C18 118.4(4) . . ? C10 C19 H19A 120.8 . . ? C18 C19 H19A 120.8 . . ? C21 C20 C25 120.5(2) . . ? C21 C20 C28 129.5(2) . . ? C25 C20 C28 109.4(2) . . ? C20 C21 C22 118.9(3) . . ? C20 C21 H21A 120.5 . . ? C22 C21 H21A 120.5 . . ? C23 C22 C21 120.9(3) . . ? C23 C22 H22A 119.5 . . ? C21 C22 H22A 119.5 . . ? C22 C23 C24 121.2(3) . . ? C22 C23 H23A 119.4 . . ? C24 C23 H23A 119.4 . . ? C23 C24 C25 118.5(3) . . ? C23 C24 H24A 120.8 . . ? C25 C24 H24A 120.8 . . ? C24 C25 C20 119.9(3) . . ? C24 C25 C26 131.1(2) . . ? C20 C25 C26 108.9(2) . . ? C27 C26 C34 116.6(2) . . ? C27 C26 C25 105.3(2) . . ? C34 C26 C25 135.6(2) . . ? C26 C27 C31 124.9(2) . . ? C26 C27 C28 115.1(2) . . ? C31 C27 C28 115.2(2) . . ? C27 C28 C29 99.32(18) . . ? C27 C28 C20 99.37(18) . . ? C29 C28 C20 128.9(2) . . ? C27 C28 C43 113.7(2) . . ? C29 C28 C43 109.66(18) . . ? C20 C28 C43 105.31(18) . . ? C38 C29 C30 119.4(2) . . ? C38 C29 C28 131.5(2) . . ? C30 C29 C28 108.9(2) . . ? C35 C30 C29 120.5(2) . . ? C35 C30 C31 130.2(2) . . ? C29 C30 C31 108.7(2) . . ? C27 C31 C32 117.0(2) . . ? C27 C31 C30 105.3(2) . . ? C32 C31 C30 134.8(2) . . ? C33 C32 C31 118.2(3) . . ? C33 C32 H32A 120.9 . . ? C31 C32 H32A 120.9 . . ? C32 C33 C34 122.7(2) . . ? C32 C33 H33A 118.6 . . ? C34 C33 H33A 118.6 . . ? C26 C34 C33 118.7(2) . . ? C26 C34 H34A 120.7 . . ? C33 C34 H34A 120.7 . . ? C36 C35 C30 119.1(3) . . ? C36 C35 H35A 120.4 . . ? C30 C35 H35A 120.4 . . ? C35 C36 C37 120.8(3) . . ? C35 C36 H36A 119.6 . . ? C37 C36 H36A 119.6 . . ? C36 C37 C38 121.1(3) . . ? C36 C37 H37A 119.5 . . ? C38 C37 H37A 119.5 . . ? C29 C38 C37 119.0(2) . . ? C29 C38 H38A 120.5 . . ? C37 C38 H38A 120.5 . . ? N1 C39 C40 129.7(2) . . ? N1 C39 C45 109.01(19) . . ? C40 C39 C45 121.3(2) . . ? C41 C40 C39 118.0(2) . . ? C41 C40 H40A 121.0 . . ? C39 C40 H40A 121.0 . . ? C40 C41 C43 122.2(2) . . ? C40 C41 H41A 118.9 . . ? C43 C41 H41A 118.9 . . ? C44 C43 C41 119.3(2) . . ? C44 C43 C28 119.9(2) . . ? C41 C43 C28 120.6(2) . . ? C43 C44 C45 119.9(2) . . ? C43 C44 H44A 120.1 . . ? C45 C44 H44A 120.1 . . ? C44 C45 C39 119.3(2) . . ? C44 C45 C46 134.3(2) . . ? C39 C45 C46 106.38(19) . . ? C51 C46 C47 119.6(2) . . ? C51 C46 C45 134.0(2) . . ? C47 C46 C45 106.3(2) . . ? N1 C47 C48 129.6(2) . . ? N1 C47 C46 109.43(19) . . ? C48 C47 C46 121.0(2) . . ? C49 C48 C47 117.8(2) . . ? C49 C48 H48A 121.1 . . ? C47 C48 H48A 121.1 . . ? C48 C49 C50 122.8(2) . . ? C48 C49 H49A 118.6 . . ? C50 C49 H49A 118.6 . . ? C51 C50 C49 118.4(2) . . ? C51 C50 C9 120.7(2) . . ? C49 C50 C9 120.8(2) . . ? C46 C51 C50 120.3(2) . . ? C46 C51 H51A 119.9 . . ? C50 C51 H51A 119.9 . . ? N1 C52 C53 112.4(2) . . ? N1 C52 H52A 109.1 . . ? C53 C52 H52A 109.1 . . ? N1 C52 H52B 109.1 . . ? C53 C52 H52B 109.1 . . ? H52A C52 H52B 107.9 . . ? C52 C53 C54 110.3(3) . . ? C52 C53 H53A 109.6 . . ? C54 C53 H53A 109.6 . . ? C52 C53 H53B 109.6 . . ? C54 C53 H53B 109.6 . . ? H53A C53 H53B 108.1 . . ? C55 C54 C53 111.4(3) . . ? C55 C54 H54A 109.4 . . ? C53 C54 H54A 109.4 . . ? C55 C54 H54B 109.4 . . ? C53 C54 H54B 109.4 . . ? H54A C54 H54B 108.0 . . ? C56 C55 C54 114.1(4) . . ? C56 C55 H55A 108.7 . . ? C54 C55 H55A 108.7 . . ? C56 C55 H55B 108.7 . . ? C54 C55 H55B 108.7 . . ? H55A C55 H55B 107.6 . . ? C55 C56 C57 115.8(5) . . ? C55 C56 H56A 108.3 . . ? C57 C56 H56A 108.3 . . ? C55 C56 H56B 108.3 . . ? C57 C56 H56B 108.3 . . ? H56A C56 H56B 107.4 . . ? C56 C57 H57A 109.5 . . ? C56 C57 H57B 109.5 . . ? H57A C57 H57B 109.5 . . ? C56 C57 H57C 109.5 . . ? H57A C57 H57C 109.5 . . ? H57B C57 H57C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C1 C2 C3 -1.8(4) . . . . ? C9 C1 C2 C3 172.7(3) . . . . ? C1 C2 C3 C4 -1.7(5) . . . . ? C2 C3 C4 C5 3.0(6) . . . . ? C3 C4 C5 C6 -0.6(5) . . . . ? C4 C5 C6 C1 -2.9(5) . . . . ? C4 C5 C6 C7 169.3(3) . . . . ? C2 C1 C6 C5 4.1(4) . . . . ? C9 C1 C6 C5 -171.5(3) . . . . ? C2 C1 C6 C7 -169.7(2) . . . . ? C9 C1 C6 C7 14.7(3) . . . . ? C5 C6 C7 C8 -177.3(3) . . . . ? C1 C6 C7 C8 -4.4(3) . . . . ? C5 C6 C7 C15 -17.6(6) . . . . ? C1 C6 C7 C15 155.3(4) . . . . ? C15 C7 C8 C12 -16.2(4) . . . . ? C6 C7 C8 C12 148.1(3) . . . . ? C15 C7 C8 C9 -172.6(3) . . . . ? C6 C7 C8 C9 -8.3(3) . . . . ? C12 C8 C9 C10 -10.1(3) . . . . ? C7 C8 C9 C10 149.1(2) . . . . ? C12 C8 C9 C1 -143.1(2) . . . . ? C7 C8 C9 C1 16.0(3) . . . . ? C12 C8 C9 C50 101.6(3) . . . . ? C7 C8 C9 C50 -99.3(3) . . . . ? C2 C1 C9 C8 167.2(3) . . . . ? C6 C1 C9 C8 -17.9(3) . . . . ? C2 C1 C9 C10 56.9(4) . . . . ? C6 C1 C9 C10 -128.2(3) . . . . ? C2 C1 C9 C50 -74.5(4) . . . . ? C6 C1 C9 C50 100.4(3) . . . . ? C8 C9 C10 C19 -180.0(3) . . . . ? C1 C9 C10 C19 -70.2(4) . . . . ? C50 C9 C10 C19 62.5(3) . . . . ? C8 C9 C10 C11 12.8(3) . . . . ? C1 C9 C10 C11 122.6(3) . . . . ? C50 C9 C10 C11 -104.8(2) . . . . ? C19 C10 C11 C16 -0.1(4) . . . . ? C9 C10 C11 C16 168.6(2) . . . . ? C19 C10 C11 C12 179.4(2) . . . . ? C9 C10 C11 C12 -11.8(3) . . . . ? C7 C8 C12 C13 15.4(4) . . . . ? C9 C8 C12 C13 171.8(2) . . . . ? C7 C8 C12 C11 -152.9(3) . . . . ? C9 C8 C12 C11 3.6(3) . . . . ? C16 C11 C12 C8 -175.2(3) . . . . ? C10 C11 C12 C8 5.4(3) . . . . ? C16 C11 C12 C13 20.3(5) . . . . ? C10 C11 C12 C13 -159.1(3) . . . . ? C8 C12 C13 C14 -3.1(4) . . . . ? C11 C12 C13 C14 160.3(3) . . . . ? C12 C13 C14 C15 -7.5(5) . . . . ? C13 C14 C15 C7 6.8(6) . . . . ? C8 C7 C15 C14 4.4(5) . . . . ? C6 C7 C15 C14 -153.7(4) . . . . ? C10 C11 C16 C17 -0.8(5) . . . . ? C12 C11 C16 C17 179.8(3) . . . . ? C11 C16 C17 C18 2.0(5) . . . . ? C16 C17 C18 C19 -2.4(6) . . . . ? C11 C10 C19 C18 -0.3(4) . . . . ? C9 C10 C19 C18 -166.3(3) . . . . ? C17 C18 C19 C10 1.5(5) . . . . ? C25 C20 C21 C22 -0.6(4) . . . . ? C28 C20 C21 C22 -170.9(2) . . . . ? C20 C21 C22 C23 1.5(4) . . . . ? C21 C22 C23 C24 -1.4(5) . . . . ? C22 C23 C24 C25 0.4(4) . . . . ? C23 C24 C25 C20 0.5(4) . . . . ? C23 C24 C25 C26 -175.1(3) . . . . ? C21 C20 C25 C24 -0.4(4) . . . . ? C28 C20 C25 C24 171.6(2) . . . . ? C21 C20 C25 C26 176.1(2) . . . . ? C28 C20 C25 C26 -11.9(3) . . . . ? C24 C25 C26 C27 -179.4(3) . . . . ? C20 C25 C26 C27 4.7(3) . . . . ? C24 C25 C26 C34 19.9(5) . . . . ? C20 C25 C26 C34 -156.0(3) . . . . ? C34 C26 C27 C31 15.6(4) . . . . ? C25 C26 C27 C31 -149.4(2) . . . . ? C34 C26 C27 C28 169.8(2) . . . . ? C25 C26 C27 C28 4.8(3) . . . . ? C26 C27 C28 C29 -143.4(2) . . . . ? C31 C27 C28 C29 13.3(3) . . . . ? C26 C27 C28 C20 -11.2(3) . . . . ? C31 C27 C28 C20 145.6(2) . . . . ? C26 C27 C28 C43 100.2(2) . . . . ? C31 C27 C28 C43 -103.1(2) . . . . ? C21 C20 C28 C27 -175.4(3) . . . . ? C25 C20 C28 C27 13.5(2) . . . . ? C21 C20 C28 C29 -65.2(4) . . . . ? C25 C20 C28 C29 123.7(3) . . . . ? C21 C20 C28 C43 66.8(3) . . . . ? C25 C20 C28 C43 -104.3(2) . . . . ? C27 C28 C29 C38 169.0(3) . . . . ? C20 C28 C29 C38 58.8(4) . . . . ? C43 C28 C29 C38 -71.7(3) . . . . ? C27 C28 C29 C30 -15.8(2) . . . . ? C20 C28 C29 C30 -125.9(2) . . . . ? C43 C28 C29 C30 103.6(2) . . . . ? C38 C29 C30 C35 2.4(4) . . . . ? C28 C29 C30 C35 -173.6(2) . . . . ? C38 C29 C30 C31 -170.3(2) . . . . ? C28 C29 C30 C31 13.8(3) . . . . ? C26 C27 C31 C32 -15.1(4) . . . . ? C28 C27 C31 C32 -169.3(2) . . . . ? C26 C27 C31 C30 148.3(2) . . . . ? C28 C27 C31 C30 -5.8(3) . . . . ? C35 C30 C31 C27 -177.0(3) . . . . ? C29 C30 C31 C27 -5.3(3) . . . . ? C35 C30 C31 C32 -17.9(5) . . . . ? C29 C30 C31 C32 153.8(3) . . . . ? C27 C31 C32 C33 4.0(4) . . . . ? C30 C31 C32 C33 -153.3(3) . . . . ? C31 C32 C33 C34 5.6(4) . . . . ? C27 C26 C34 C33 -5.1(4) . . . . ? C25 C26 C34 C33 154.1(3) . . . . ? C32 C33 C34 C26 -5.0(4) . . . . ? C29 C30 C35 C36 -1.5(4) . . . . ? C31 C30 C35 C36 169.3(3) . . . . ? C30 C35 C36 C37 -0.6(4) . . . . ? C35 C36 C37 C38 1.9(5) . . . . ? C30 C29 C38 C37 -1.1(4) . . . . ? C28 C29 C38 C37 173.8(3) . . . . ? C36 C37 C38 C29 -1.0(4) . . . . ? C47 N1 C39 C40 -179.6(2) . . . . ? C52 N1 C39 C40 -2.7(4) . . . . ? C47 N1 C39 C45 0.5(2) . . . . ? C52 N1 C39 C45 177.4(2) . . . . ? N1 C39 C40 C41 179.3(2) . . . . ? C45 C39 C40 C41 -0.8(3) . . . . ? C39 C40 C41 C43 -0.7(3) . . . . ? C40 C41 C43 C44 1.7(3) . . . . ? C40 C41 C43 C28 -173.4(2) . . . . ? C27 C28 C43 C44 172.4(2) . . . . ? C29 C28 C43 C44 62.2(3) . . . . ? C20 C28 C43 C44 -79.9(2) . . . . ? C27 C28 C43 C41 -12.6(3) . . . . ? C29 C28 C43 C41 -122.7(2) . . . . ? C20 C28 C43 C41 95.2(2) . . . . ? C41 C43 C44 C45 -1.3(3) . . . . ? C28 C43 C44 C45 173.84(19) . . . . ? C43 C44 C45 C39 -0.1(3) . . . . ? C43 C44 C45 C46 -178.8(2) . . . . ? N1 C39 C45 C44 -178.94(19) . . . . ? C40 C39 C45 C44 1.1(3) . . . . ? N1 C39 C45 C46 0.1(2) . . . . ? C40 C39 C45 C46 -179.8(2) . . . . ? C44 C45 C46 C51 -2.8(4) . . . . ? C39 C45 C46 C51 178.4(2) . . . . ? C44 C45 C46 C47 178.2(2) . . . . ? C39 C45 C46 C47 -0.6(2) . . . . ? C39 N1 C47 C48 179.5(2) . . . . ? C52 N1 C47 C48 2.6(4) . . . . ? C39 N1 C47 C46 -0.9(2) . . . . ? C52 N1 C47 C46 -177.8(2) . . . . ? C51 C46 C47 N1 -178.2(2) . . . . ? C45 C46 C47 N1 1.0(2) . . . . ? C51 C46 C47 C48 1.4(3) . . . . ? C45 C46 C47 C48 -179.4(2) . . . . ? N1 C47 C48 C49 178.2(2) . . . . ? C46 C47 C48 C49 -1.4(3) . . . . ? C47 C48 C49 C50 0.1(4) . . . . ? C48 C49 C50 C51 1.0(4) . . . . ? C48 C49 C50 C9 178.3(2) . . . . ? C8 C9 C50 C51 -27.0(3) . . . . ? C10 C9 C50 C51 81.1(3) . . . . ? C1 C9 C50 C51 -135.7(2) . . . . ? C8 C9 C50 C49 155.8(2) . . . . ? C10 C9 C50 C49 -96.1(3) . . . . ? C1 C9 C50 C49 47.1(3) . . . . ? C47 C46 C51 C50 -0.2(3) . . . . ? C45 C46 C51 C50 -179.1(2) . . . . ? C49 C50 C51 C46 -1.0(3) . . . . ? C9 C50 C51 C46 -178.3(2) . . . . ? C47 N1 C52 C53 93.4(3) . . . . ? C39 N1 C52 C53 -82.9(3) . . . . ? N1 C52 C53 C54 -177.5(3) . . . . ? C52 C53 C54 C55 178.8(4) . . . . ? C53 C54 C55 C56 -174.4(5) . . . . ? C54 C55 C56 C57 71.5(6) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.01 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.597 _refine_diff_density_min -0.343 _refine_diff_density_rms 0.047 # Attachment '- 4ca.cif' data_z4 _database_code_depnum_ccdc_archive 'CCDC 801487' #TrackingRef '- 4ca.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C37 H25 N' _chemical_formula_weight 483.58 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 8.2045(4) _cell_length_b 28.7349(14) _cell_length_c 10.9365(5) _cell_angle_alpha 90.00 _cell_angle_beta 96.475(2) _cell_angle_gamma 90.00 _cell_volume 2561.9(2) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.52 _exptl_crystal_size_mid 0.36 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.254 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1016 _exptl_absorpt_coefficient_mu 0.072 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9636 _exptl_absorpt_correction_T_max 0.9900 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 29335 _diffrn_reflns_av_R_equivalents 0.1344 _diffrn_reflns_av_sigmaI/netI 0.0870 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -34 _diffrn_reflns_limit_k_max 34 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.00 _diffrn_reflns_theta_max 25.01 _reflns_number_total 4506 _reflns_number_gt 2519 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0470P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4506 _refine_ls_number_parameters 343 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1211 _refine_ls_R_factor_gt 0.0509 _refine_ls_wR_factor_ref 0.1184 _refine_ls_wR_factor_gt 0.0956 _refine_ls_goodness_of_fit_ref 0.998 _refine_ls_restrained_S_all 0.998 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N1 N 1.0823(3) 0.74467(6) 0.4885(2) 0.0550(6) Uani 1 1 d . . . C1 C 1.2348(3) 0.74149(8) 0.5632(2) 0.0430(6) Uani 1 1 d . . . C2 C 1.3397(4) 0.70546(9) 0.5474(3) 0.0664(9) Uani 1 1 d . . . H2A H 1.3095 0.6824 0.4867 0.080 Uiso 1 1 calc R . . C3 C 1.4883(4) 0.70239(11) 0.6185(4) 0.0970(12) Uani 1 1 d . . . H3A H 1.5595 0.6770 0.6077 0.116 Uiso 1 1 calc R . . C4 C 1.5337(4) 0.73536(12) 0.7042(4) 0.0962(13) Uani 1 1 d . . . H4A H 1.6372 0.7334 0.7525 0.115 Uiso 1 1 calc R . . C5 C 1.4299(4) 0.77132(11) 0.7205(3) 0.0797(10) Uani 1 1 d . . . H5A H 1.4619 0.7946 0.7802 0.096 Uiso 1 1 calc R . . C6 C 1.2793(3) 0.77426(9) 0.6513(2) 0.0571(8) Uani 1 1 d . . . H6A H 1.2065 0.7990 0.6648 0.069 Uiso 1 1 calc R . . C7 C 1.0174(4) 0.78882(8) 0.4510(2) 0.0512(7) Uani 1 1 d . . . C8 C 1.1160(4) 0.82148(9) 0.4020(2) 0.0628(8) Uani 1 1 d . . . H8A H 1.2268 0.8141 0.3930 0.075 Uiso 1 1 calc R . . C9 C 1.0542(5) 0.86479(10) 0.3661(3) 0.0746(10) Uani 1 1 d . . . H9A H 1.1217 0.8870 0.3316 0.090 Uiso 1 1 calc R . . C10 C 0.8959(6) 0.87532(11) 0.3808(3) 0.0855(11) Uani 1 1 d . . . H10A H 0.8540 0.9052 0.3570 0.103 Uiso 1 1 calc R . . C11 C 0.7956(4) 0.84378(12) 0.4293(3) 0.0859(11) Uani 1 1 d . . . H11A H 0.6851 0.8516 0.4384 0.103 Uiso 1 1 calc R . . C12 C 0.8577(4) 0.80008(10) 0.4650(3) 0.0676(9) Uani 1 1 d . . . H12A H 0.7894 0.7780 0.4991 0.081 Uiso 1 1 calc R . . C13 C 0.6461(3) 0.55982(7) 0.1691(2) 0.0356(6) Uani 1 1 d . . . C14 C 0.6872(3) 0.53688(9) 0.0654(2) 0.0484(7) Uani 1 1 d . . . H14A H 0.6228 0.5408 -0.0117 0.058 Uiso 1 1 calc R . . C15 C 0.8238(3) 0.50823(9) 0.0761(3) 0.0538(7) Uani 1 1 d . . . H15A H 0.8516 0.4918 0.0060 0.065 Uiso 1 1 calc R . . C16 C 0.9199(3) 0.50325(9) 0.1872(3) 0.0511(7) Uani 1 1 d . . . H16A H 1.0141 0.4838 0.1924 0.061 Uiso 1 1 calc R . . C17 C 0.8807(3) 0.52629(8) 0.2914(2) 0.0403(6) Uani 1 1 d . . . H17A H 0.9486 0.5233 0.3674 0.048 Uiso 1 1 calc R . . C18 C 0.7423(3) 0.55348(7) 0.2831(2) 0.0318(6) Uani 1 1 d . . . C19 C 0.6728(3) 0.58282(7) 0.38212(19) 0.0304(5) Uani 1 1 d . . . C20 C 0.5122(3) 0.59622(7) 0.3125(2) 0.0307(5) Uani 1 1 d . . . C21 C 0.4971(3) 0.58642(7) 0.1888(2) 0.0351(6) Uani 1 1 d . . . C22 C 0.3413(3) 0.59195(8) 0.1246(2) 0.0467(7) Uani 1 1 d . . . H22A H 0.3244 0.5883 0.0378 0.056 Uiso 1 1 calc R . . C23 C 0.2116(3) 0.60297(8) 0.1906(3) 0.0495(7) Uani 1 1 d . . . H23A H 0.1080 0.6099 0.1465 0.059 Uiso 1 1 calc R . . C24 C 0.2270(3) 0.60424(7) 0.3185(2) 0.0436(6) Uani 1 1 d . . . H24A H 0.1337 0.6086 0.3614 0.052 Uiso 1 1 calc R . . C25 C 0.3829(3) 0.59896(7) 0.3820(2) 0.0338(6) Uani 1 1 d . . . C26 C 0.4468(3) 0.58063(7) 0.5048(2) 0.0332(6) Uani 1 1 d . . . C27 C 0.6092(3) 0.56433(7) 0.4992(2) 0.0308(5) Uani 1 1 d . . . C28 C 0.6853(3) 0.53818(8) 0.5950(2) 0.0394(6) Uani 1 1 d . . . H28A H 0.7924 0.5261 0.5909 0.047 Uiso 1 1 calc R . . C29 C 0.6038(3) 0.52977(8) 0.6972(2) 0.0471(7) Uani 1 1 d . . . H29A H 0.6545 0.5111 0.7625 0.057 Uiso 1 1 calc R . . C30 C 0.4507(3) 0.54804(8) 0.7051(2) 0.0490(7) Uani 1 1 d . . . H30A H 0.3995 0.5433 0.7778 0.059 Uiso 1 1 calc R . . C31 C 0.3699(3) 0.57317(8) 0.6088(2) 0.0441(6) Uani 1 1 d . . . H31A H 0.2631 0.5851 0.6143 0.053 Uiso 1 1 calc R . . C32 C 0.7856(3) 0.62544(7) 0.4126(2) 0.0309(5) Uani 1 1 d . . . C33 C 0.8063(3) 0.65820(7) 0.3223(2) 0.0382(6) Uani 1 1 d . . . H33A H 0.7518 0.6538 0.2418 0.046 Uiso 1 1 calc R . . C34 C 0.9039(3) 0.69683(8) 0.3465(2) 0.0435(7) Uani 1 1 d . . . H34A H 0.9159 0.7185 0.2826 0.052 Uiso 1 1 calc R . . C35 C 0.9847(3) 0.70445(7) 0.4630(2) 0.0401(6) Uani 1 1 d . . . C36 C 0.9666(3) 0.67190(8) 0.5524(2) 0.0485(7) Uani 1 1 d . . . H36A H 1.0219 0.6762 0.6327 0.058 Uiso 1 1 calc R . . C37 C 0.8695(3) 0.63295(8) 0.5278(2) 0.0422(6) Uani 1 1 d . . . H37A H 0.8602 0.6109 0.5913 0.051 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.0497(15) 0.0287(11) 0.0790(16) 0.0045(11) -0.0262(13) -0.0081(10) C1 0.0384(17) 0.0318(14) 0.0550(17) -0.0012(12) -0.0117(14) -0.0049(12) C2 0.051(2) 0.0487(18) 0.095(2) -0.0244(16) -0.0140(17) 0.0004(15) C3 0.048(2) 0.059(2) 0.175(4) -0.021(2) -0.026(2) 0.0084(18) C4 0.069(3) 0.063(2) 0.141(3) 0.001(2) -0.056(2) -0.011(2) C5 0.085(3) 0.061(2) 0.084(2) -0.0144(18) -0.032(2) -0.016(2) C6 0.0517(19) 0.0430(16) 0.0718(19) -0.0164(15) -0.0144(16) -0.0028(14) C7 0.060(2) 0.0313(14) 0.0557(17) -0.0033(12) -0.0201(15) -0.0045(14) C8 0.081(2) 0.0438(17) 0.0581(19) 0.0004(14) -0.0148(16) -0.0120(16) C9 0.123(3) 0.0449(19) 0.0504(19) 0.0035(15) -0.016(2) -0.012(2) C10 0.134(4) 0.0430(19) 0.071(2) -0.0005(17) -0.026(2) 0.012(2) C11 0.089(3) 0.060(2) 0.102(3) -0.013(2) -0.017(2) 0.022(2) C12 0.064(2) 0.0489(18) 0.085(2) 0.0000(16) -0.0111(18) 0.0032(16) C13 0.0413(16) 0.0335(13) 0.0317(14) 0.0006(11) 0.0031(12) -0.0099(11) C14 0.0554(18) 0.0539(16) 0.0371(15) -0.0042(12) 0.0102(14) -0.0140(14) C15 0.0524(19) 0.0591(18) 0.0538(18) -0.0197(14) 0.0231(16) -0.0153(15) C16 0.0364(16) 0.0515(16) 0.0679(19) -0.0147(15) 0.0168(15) -0.0004(13) C17 0.0325(15) 0.0375(14) 0.0504(16) -0.0034(12) 0.0027(12) -0.0021(12) C18 0.0323(14) 0.0285(12) 0.0346(14) -0.0018(10) 0.0037(11) -0.0058(11) C19 0.0292(14) 0.0290(12) 0.0321(13) -0.0007(10) -0.0010(11) -0.0028(10) C20 0.0293(14) 0.0226(12) 0.0385(14) -0.0001(10) -0.0042(12) -0.0007(10) C21 0.0367(16) 0.0312(13) 0.0350(14) 0.0040(10) -0.0066(12) -0.0060(11) C22 0.0543(19) 0.0400(15) 0.0418(15) 0.0043(12) -0.0117(15) -0.0088(13) C23 0.0383(17) 0.0420(15) 0.064(2) 0.0065(13) -0.0131(15) 0.0008(13) C24 0.0298(16) 0.0361(14) 0.0637(18) -0.0011(12) 0.0006(14) 0.0013(11) C25 0.0279(15) 0.0251(12) 0.0472(15) -0.0051(11) -0.0006(12) 0.0001(10) C26 0.0340(15) 0.0288(12) 0.0371(14) -0.0051(11) 0.0048(12) -0.0048(11) C27 0.0312(14) 0.0280(12) 0.0322(13) -0.0038(10) -0.0003(11) -0.0062(11) C28 0.0369(15) 0.0383(14) 0.0412(15) -0.0004(12) -0.0030(13) -0.0016(12) C29 0.062(2) 0.0416(15) 0.0365(15) 0.0074(12) 0.0006(14) -0.0110(14) C30 0.0579(19) 0.0506(16) 0.0406(16) -0.0055(13) 0.0153(15) -0.0195(14) C31 0.0410(16) 0.0446(15) 0.0481(16) -0.0048(13) 0.0111(13) -0.0054(13) C32 0.0284(14) 0.0280(12) 0.0353(14) -0.0019(11) -0.0003(11) -0.0011(10) C33 0.0385(15) 0.0359(14) 0.0372(14) 0.0005(11) -0.0097(11) -0.0062(12) C34 0.0417(16) 0.0346(14) 0.0509(17) 0.0110(12) -0.0088(14) -0.0040(12) C35 0.0368(16) 0.0285(13) 0.0517(17) -0.0026(12) -0.0098(13) -0.0033(11) C36 0.0558(18) 0.0454(15) 0.0400(15) -0.0012(13) -0.0132(13) -0.0097(14) C37 0.0487(17) 0.0397(14) 0.0356(15) 0.0045(11) -0.0064(13) -0.0108(12) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C35 1.416(3) . ? N1 C1 1.418(3) . ? N1 C7 1.418(3) . ? C1 C6 1.367(3) . ? C1 C2 1.370(3) . ? C2 C3 1.373(4) . ? C2 H2A 0.9500 . ? C3 C4 1.355(4) . ? C3 H3A 0.9500 . ? C4 C5 1.364(4) . ? C4 H4A 0.9500 . ? C5 C6 1.377(4) . ? C5 H5A 0.9500 . ? C6 H6A 0.9500 . ? C7 C12 1.375(4) . ? C7 C8 1.385(4) . ? C8 C9 1.384(4) . ? C8 H8A 0.9500 . ? C9 C10 1.360(4) . ? C9 H9A 0.9500 . ? C10 C11 1.370(5) . ? C10 H10A 0.9500 . ? C11 C12 1.394(4) . ? C11 H11A 0.9500 . ? C12 H12A 0.9500 . ? C13 C14 1.386(3) . ? C13 C18 1.410(3) . ? C13 C21 1.478(3) . ? C14 C15 1.385(3) . ? C14 H14A 0.9500 . ? C15 C16 1.380(3) . ? C15 H15A 0.9500 . ? C16 C17 1.387(3) . ? C16 H16A 0.9500 . ? C17 C18 1.373(3) . ? C17 H17A 0.9500 . ? C18 C19 1.532(3) . ? C19 C20 1.496(3) . ? C19 C27 1.531(3) . ? C19 C32 1.549(3) . ? C20 C21 1.374(3) . ? C20 C25 1.376(3) . ? C21 C22 1.396(3) . ? C22 C23 1.388(3) . ? C22 H22A 0.9500 . ? C23 C24 1.391(3) . ? C23 H23A 0.9500 . ? C24 C25 1.394(3) . ? C24 H24A 0.9500 . ? C25 C26 1.482(3) . ? C26 C31 1.378(3) . ? C26 C27 1.420(3) . ? C27 C28 1.380(3) . ? C28 C29 1.387(3) . ? C28 H28A 0.9500 . ? C29 C30 1.373(3) . ? C29 H29A 0.9500 . ? C30 C31 1.383(3) . ? C30 H30A 0.9500 . ? C31 H31A 0.9500 . ? C32 C37 1.382(3) . ? C32 C33 1.389(3) . ? C33 C34 1.377(3) . ? C33 H33A 0.9500 . ? C34 C35 1.385(3) . ? C34 H34A 0.9500 . ? C35 C36 1.373(3) . ? C36 C37 1.383(3) . ? C36 H36A 0.9500 . ? C37 H37A 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C35 N1 C1 120.27(19) . . ? C35 N1 C7 119.2(2) . . ? C1 N1 C7 120.2(2) . . ? C6 C1 C2 119.2(3) . . ? C6 C1 N1 120.7(2) . . ? C2 C1 N1 120.1(2) . . ? C1 C2 C3 120.5(3) . . ? C1 C2 H2A 119.8 . . ? C3 C2 H2A 119.8 . . ? C4 C3 C2 120.3(3) . . ? C4 C3 H3A 119.9 . . ? C2 C3 H3A 119.9 . . ? C3 C4 C5 119.6(3) . . ? C3 C4 H4A 120.2 . . ? C5 C4 H4A 120.2 . . ? C4 C5 C6 120.6(3) . . ? C4 C5 H5A 119.7 . . ? C6 C5 H5A 119.7 . . ? C1 C6 C5 119.8(3) . . ? C1 C6 H6A 120.1 . . ? C5 C6 H6A 120.1 . . ? C12 C7 C8 119.3(3) . . ? C12 C7 N1 120.6(3) . . ? C8 C7 N1 120.1(3) . . ? C9 C8 C7 120.5(3) . . ? C9 C8 H8A 119.7 . . ? C7 C8 H8A 119.7 . . ? C10 C9 C8 119.4(3) . . ? C10 C9 H9A 120.3 . . ? C8 C9 H9A 120.3 . . ? C9 C10 C11 121.4(3) . . ? C9 C10 H10A 119.3 . . ? C11 C10 H10A 119.3 . . ? C10 C11 C12 119.2(3) . . ? C10 C11 H11A 120.4 . . ? C12 C11 H11A 120.4 . . ? C7 C12 C11 120.2(3) . . ? C7 C12 H12A 119.9 . . ? C11 C12 H12A 119.9 . . ? C14 C13 C18 119.9(2) . . ? C14 C13 C21 130.3(2) . . ? C18 C13 C21 109.17(19) . . ? C15 C14 C13 118.9(2) . . ? C15 C14 H14A 120.5 . . ? C13 C14 H14A 120.5 . . ? C16 C15 C14 120.8(2) . . ? C16 C15 H15A 119.6 . . ? C14 C15 H15A 119.6 . . ? C15 C16 C17 120.8(2) . . ? C15 C16 H16A 119.6 . . ? C17 C16 H16A 119.6 . . ? C18 C17 C16 118.9(2) . . ? C18 C17 H17A 120.5 . . ? C16 C17 H17A 120.5 . . ? C17 C18 C13 120.6(2) . . ? C17 C18 C19 129.6(2) . . ? C13 C18 C19 109.74(19) . . ? C20 C19 C27 98.71(17) . . ? C20 C19 C18 99.12(17) . . ? C27 C19 C18 126.10(17) . . ? C20 C19 C32 112.13(17) . . ? C27 C19 C32 110.24(16) . . ? C18 C19 C32 109.04(17) . . ? C21 C20 C25 124.5(2) . . ? C21 C20 C19 115.17(19) . . ? C25 C20 C19 115.0(2) . . ? C20 C21 C22 116.6(2) . . ? C20 C21 C13 105.33(19) . . ? C22 C21 C13 135.3(2) . . ? C23 C22 C21 118.5(2) . . ? C23 C22 H22A 120.8 . . ? C21 C22 H22A 120.8 . . ? C22 C23 C24 122.7(2) . . ? C22 C23 H23A 118.6 . . ? C24 C23 H23A 118.6 . . ? C23 C24 C25 118.2(2) . . ? C23 C24 H24A 120.9 . . ? C25 C24 H24A 120.9 . . ? C20 C25 C24 116.9(2) . . ? C20 C25 C26 105.33(19) . . ? C24 C25 C26 134.5(2) . . ? C31 C26 C27 120.2(2) . . ? C31 C26 C25 130.9(2) . . ? C27 C26 C25 108.44(19) . . ? C28 C27 C26 119.6(2) . . ? C28 C27 C19 131.0(2) . . ? C26 C27 C19 109.34(18) . . ? C27 C28 C29 119.2(2) . . ? C27 C28 H28A 120.4 . . ? C29 C28 H28A 120.4 . . ? C30 C29 C28 120.8(2) . . ? C30 C29 H29A 119.6 . . ? C28 C29 H29A 119.6 . . ? C29 C30 C31 121.0(2) . . ? C29 C30 H30A 119.5 . . ? C31 C30 H30A 119.5 . . ? C26 C31 C30 119.0(2) . . ? C26 C31 H31A 120.5 . . ? C30 C31 H31A 120.5 . . ? C37 C32 C33 117.0(2) . . ? C37 C32 C19 122.94(19) . . ? C33 C32 C19 120.06(19) . . ? C34 C33 C32 121.6(2) . . ? C34 C33 H33A 119.2 . . ? C32 C33 H33A 119.2 . . ? C33 C34 C35 120.8(2) . . ? C33 C34 H34A 119.6 . . ? C35 C34 H34A 119.6 . . ? C36 C35 C34 117.9(2) . . ? C36 C35 N1 121.3(2) . . ? C34 C35 N1 120.8(2) . . ? C35 C36 C37 121.2(2) . . ? C35 C36 H36A 119.4 . . ? C37 C36 H36A 119.4 . . ? C32 C37 C36 121.4(2) . . ? C32 C37 H37A 119.3 . . ? C36 C37 H37A 119.3 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C35 N1 C1 C6 -137.1(3) . . . . ? C7 N1 C1 C6 35.3(4) . . . . ? C35 N1 C1 C2 43.1(4) . . . . ? C7 N1 C1 C2 -144.4(3) . . . . ? C6 C1 C2 C3 -0.4(4) . . . . ? N1 C1 C2 C3 179.3(3) . . . . ? C1 C2 C3 C4 -0.9(5) . . . . ? C2 C3 C4 C5 0.9(6) . . . . ? C3 C4 C5 C6 0.3(6) . . . . ? C2 C1 C6 C5 1.6(4) . . . . ? N1 C1 C6 C5 -178.1(3) . . . . ? C4 C5 C6 C1 -1.6(5) . . . . ? C35 N1 C7 C12 41.9(4) . . . . ? C1 N1 C7 C12 -130.7(3) . . . . ? C35 N1 C7 C8 -139.4(2) . . . . ? C1 N1 C7 C8 48.0(3) . . . . ? C12 C7 C8 C9 -0.7(4) . . . . ? N1 C7 C8 C9 -179.4(2) . . . . ? C7 C8 C9 C10 0.8(4) . . . . ? C8 C9 C10 C11 -0.7(5) . . . . ? C9 C10 C11 C12 0.4(5) . . . . ? C8 C7 C12 C11 0.5(4) . . . . ? N1 C7 C12 C11 179.2(2) . . . . ? C10 C11 C12 C7 -0.3(5) . . . . ? C18 C13 C14 C15 -0.4(3) . . . . ? C21 C13 C14 C15 -169.9(2) . . . . ? C13 C14 C15 C16 -1.4(4) . . . . ? C14 C15 C16 C17 1.0(4) . . . . ? C15 C16 C17 C18 1.4(4) . . . . ? C16 C17 C18 C13 -3.2(3) . . . . ? C16 C17 C18 C19 -179.1(2) . . . . ? C14 C13 C18 C17 2.8(3) . . . . ? C21 C13 C18 C17 174.34(19) . . . . ? C14 C13 C18 C19 179.38(19) . . . . ? C21 C13 C18 C19 -9.1(2) . . . . ? C17 C18 C19 C20 -172.1(2) . . . . ? C13 C18 C19 C20 11.7(2) . . . . ? C17 C18 C19 C27 -64.2(3) . . . . ? C13 C18 C19 C27 119.6(2) . . . . ? C17 C18 C19 C32 70.6(3) . . . . ? C13 C18 C19 C32 -105.6(2) . . . . ? C27 C19 C20 C21 -140.11(18) . . . . ? C18 C19 C20 C21 -11.2(2) . . . . ? C32 C19 C20 C21 103.8(2) . . . . ? C27 C19 C20 C25 15.4(2) . . . . ? C18 C19 C20 C25 144.34(18) . . . . ? C32 C19 C20 C25 -100.7(2) . . . . ? C25 C20 C21 C22 17.8(3) . . . . ? C19 C20 C21 C22 170.69(19) . . . . ? C25 C20 C21 C13 -146.4(2) . . . . ? C19 C20 C21 C13 6.5(2) . . . . ? C14 C13 C21 C20 172.3(2) . . . . ? C18 C13 C21 C20 1.9(2) . . . . ? C14 C13 C21 C22 12.5(4) . . . . ? C18 C13 C21 C22 -157.9(2) . . . . ? C20 C21 C22 C23 -5.3(3) . . . . ? C13 C21 C22 C23 152.8(2) . . . . ? C21 C22 C23 C24 -6.5(3) . . . . ? C22 C23 C24 C25 6.8(3) . . . . ? C21 C20 C25 C24 -17.5(3) . . . . ? C19 C20 C25 C24 -170.40(18) . . . . ? C21 C20 C25 C26 145.3(2) . . . . ? C19 C20 C25 C26 -7.7(2) . . . . ? C23 C24 C25 C20 4.6(3) . . . . ? C23 C24 C25 C26 -151.7(2) . . . . ? C20 C25 C26 C31 -176.6(2) . . . . ? C24 C25 C26 C31 -18.5(4) . . . . ? C20 C25 C26 C27 -4.5(2) . . . . ? C24 C25 C26 C27 153.6(2) . . . . ? C31 C26 C27 C28 4.5(3) . . . . ? C25 C26 C27 C28 -168.58(18) . . . . ? C31 C26 C27 C19 -172.38(19) . . . . ? C25 C26 C27 C19 14.5(2) . . . . ? C20 C19 C27 C28 166.2(2) . . . . ? C18 C19 C27 C28 58.1(3) . . . . ? C32 C19 C27 C28 -76.3(3) . . . . ? C20 C19 C27 C26 -17.4(2) . . . . ? C18 C19 C27 C26 -125.5(2) . . . . ? C32 C19 C27 C26 100.2(2) . . . . ? C26 C27 C28 C29 -2.4(3) . . . . ? C19 C27 C28 C29 173.7(2) . . . . ? C27 C28 C29 C30 -1.6(3) . . . . ? C28 C29 C30 C31 3.5(4) . . . . ? C27 C26 C31 C30 -2.6(3) . . . . ? C25 C26 C31 C30 168.7(2) . . . . ? C29 C30 C31 C26 -1.4(3) . . . . ? C20 C19 C32 C37 133.8(2) . . . . ? C27 C19 C32 C37 24.9(3) . . . . ? C18 C19 C32 C37 -117.5(2) . . . . ? C20 C19 C32 C33 -46.3(3) . . . . ? C27 C19 C32 C33 -155.2(2) . . . . ? C18 C19 C32 C33 62.5(2) . . . . ? C37 C32 C33 C34 -1.0(3) . . . . ? C19 C32 C33 C34 179.1(2) . . . . ? C32 C33 C34 C35 -0.3(4) . . . . ? C33 C34 C35 C36 1.1(4) . . . . ? C33 C34 C35 N1 -178.7(2) . . . . ? C1 N1 C35 C36 41.0(3) . . . . ? C7 N1 C35 C36 -131.5(3) . . . . ? C1 N1 C35 C34 -139.2(2) . . . . ? C7 N1 C35 C34 48.3(3) . . . . ? C34 C35 C36 C37 -0.7(4) . . . . ? N1 C35 C36 C37 179.1(2) . . . . ? C33 C32 C37 C36 1.4(3) . . . . ? C19 C32 C37 C36 -178.7(2) . . . . ? C35 C36 C37 C32 -0.6(4) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.01 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.158 _refine_diff_density_min -0.204 _refine_diff_density_rms 0.039 # Attachment '- 4cb.cif' data_z5 _database_code_depnum_ccdc_archive 'CCDC 801488' #TrackingRef '- 4cb.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C56 H35 N' _chemical_formula_weight 721.85 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.1129(3) _cell_length_b 9.2093(3) _cell_length_c 27.8672(10) _cell_angle_alpha 88.7640(10) _cell_angle_beta 83.5200(10) _cell_angle_gamma 65.0790(10) _cell_volume 1875.37(11) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.32 _exptl_crystal_size_min 0.26 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.278 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 756 _exptl_absorpt_coefficient_mu 0.073 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9728 _exptl_absorpt_correction_T_max 0.9812 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 22085 _diffrn_reflns_av_R_equivalents 0.0339 _diffrn_reflns_av_sigmaI/netI 0.0355 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -33 _diffrn_reflns_limit_l_max 33 _diffrn_reflns_theta_min 1.47 _diffrn_reflns_theta_max 25.00 _reflns_number_total 6577 _reflns_number_gt 4703 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0434P)^2^+0.3339P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6577 _refine_ls_number_parameters 514 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0644 _refine_ls_R_factor_gt 0.0405 _refine_ls_wR_factor_ref 0.1050 _refine_ls_wR_factor_gt 0.0917 _refine_ls_goodness_of_fit_ref 1.018 _refine_ls_restrained_S_all 1.018 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N1 N 0.6054(2) 0.36327(17) 0.25508(5) 0.0516(4) Uani 1 1 d . . . C1 C -0.0520(3) 0.7361(2) 0.08481(7) 0.0514(5) Uani 1 1 d . . . C2 C -0.1913(3) 0.8884(3) 0.08732(8) 0.0626(6) Uani 1 1 d . . . H2A H -0.1829 0.9664 0.0667 0.075 Uiso 1 1 calc R . . C3 C -0.3439(3) 0.9242(3) 0.12079(8) 0.0688(6) Uani 1 1 d . . . H3A H -0.4380 1.0269 0.1226 0.083 Uiso 1 1 calc R . . C4 C -0.3582(3) 0.8096(3) 0.15142(8) 0.0642(6) Uani 1 1 d . . . H4A H -0.4639 0.8344 0.1727 0.077 Uiso 1 1 calc R . . C5 C -0.2165(2) 0.6579(2) 0.15074(7) 0.0518(5) Uani 1 1 d . . . H5A H -0.2250 0.5820 0.1722 0.062 Uiso 1 1 calc R . . C6 C -0.0628(2) 0.6202(2) 0.11803(6) 0.0436(4) Uani 1 1 d . . . C7 C 0.1146(2) 0.4667(2) 0.11032(6) 0.0399(4) Uani 1 1 d . . . C8 C 0.1863(2) 0.4968(2) 0.06115(6) 0.0453(4) Uani 1 1 d . . . C9 C 0.1053(3) 0.6532(2) 0.04731(7) 0.0526(5) Uani 1 1 d . . . C10 C 0.1500(3) 0.6812(3) -0.00107(8) 0.0685(6) Uani 1 1 d . . . H10A H 0.1086 0.7848 -0.0125 0.082 Uiso 1 1 calc R . . C11 C 0.2579(3) 0.5497(4) -0.03156(7) 0.0733(7) Uani 1 1 d . . . H11A H 0.2975 0.5683 -0.0627 0.088 Uiso 1 1 calc R . . C12 C 0.3093(3) 0.3924(3) -0.01788(7) 0.0654(6) Uani 1 1 d . . . H12A H 0.3711 0.3078 -0.0402 0.078 Uiso 1 1 calc R . . C13 C 0.2659(2) 0.3648(3) 0.03019(6) 0.0511(5) Uani 1 1 d . . . C14 C 0.2376(2) 0.2346(2) 0.05624(6) 0.0482(5) Uani 1 1 d . . . C15 C 0.1340(2) 0.2958(2) 0.10130(6) 0.0429(4) Uani 1 1 d . . . C16 C 0.0852(2) 0.1976(2) 0.13210(7) 0.0529(5) Uani 1 1 d . . . H16A H 0.0216 0.2361 0.1624 0.063 Uiso 1 1 calc R . . C17 C 0.1318(3) 0.0408(3) 0.11747(9) 0.0680(6) Uani 1 1 d . . . H17A H 0.0968 -0.0251 0.1378 0.082 Uiso 1 1 calc R . . C18 C 0.2286(3) -0.0178(3) 0.07337(9) 0.0707(6) Uani 1 1 d . . . H18A H 0.2582 -0.1231 0.0641 0.085 Uiso 1 1 calc R . . C19 C 0.2827(3) 0.0764(3) 0.04258(8) 0.0632(6) Uani 1 1 d . . . H19A H 0.3490 0.0350 0.0128 0.076 Uiso 1 1 calc R . . C20 C 0.8010(2) 0.72143(19) 0.44427(6) 0.0398(4) Uani 1 1 d . . . C21 C 0.9789(2) 0.6624(2) 0.45607(7) 0.0480(4) Uani 1 1 d . . . H21A H 1.0075 0.6139 0.4855 0.058 Uiso 1 1 calc R . . C22 C 1.1131(2) 0.6763(2) 0.42372(8) 0.0572(5) Uani 1 1 d . . . H22A H 1.2325 0.6366 0.4315 0.069 Uiso 1 1 calc R . . C23 C 1.0727(3) 0.7482(3) 0.38003(8) 0.0611(5) Uani 1 1 d . . . H23A H 1.1648 0.7572 0.3588 0.073 Uiso 1 1 calc R . . C24 C 0.8964(2) 0.8070(2) 0.36741(7) 0.0520(5) Uani 1 1 d . . . H24A H 0.8702 0.8533 0.3376 0.062 Uiso 1 1 calc R . . C25 C 0.7602(2) 0.79615(19) 0.39955(6) 0.0388(4) Uani 1 1 d . . . C26 C 0.5595(2) 0.84036(19) 0.39328(5) 0.0353(4) Uani 1 1 d . . . C27 C 0.4930(2) 0.81611(19) 0.44360(5) 0.0345(4) Uani 1 1 d . . . C28 C 0.6275(2) 0.73908(19) 0.47299(6) 0.0382(4) Uani 1 1 d . . . C29 C 0.5699(2) 0.7333(2) 0.52183(6) 0.0461(4) Uani 1 1 d . . . H29A H 0.6529 0.6754 0.5432 0.055 Uiso 1 1 calc R . . C30 C 0.3849(3) 0.8167(2) 0.53769(6) 0.0477(4) Uani 1 1 d . . . H30A H 0.3437 0.8050 0.5694 0.057 Uiso 1 1 calc R . . C31 C 0.2583(2) 0.9170(2) 0.50821(6) 0.0432(4) Uani 1 1 d . . . H31A H 0.1381 0.9798 0.5208 0.052 Uiso 1 1 calc R . . C32 C 0.3158(2) 0.92075(19) 0.45952(6) 0.0373(4) Uani 1 1 d . . . C33 C 0.2588(2) 1.0407(2) 0.42116(6) 0.0382(4) Uani 1 1 d . . . C34 C 0.4106(2) 1.00735(19) 0.38565(6) 0.0372(4) Uani 1 1 d . . . C35 C 0.4041(3) 1.1185(2) 0.35108(6) 0.0478(4) Uani 1 1 d . . . H35A H 0.5039 1.0989 0.3280 0.057 Uiso 1 1 calc R . . C36 C 0.2467(3) 1.2601(2) 0.35111(7) 0.0582(5) Uani 1 1 d . . . H36A H 0.2431 1.3366 0.3284 0.070 Uiso 1 1 calc R . . C37 C 0.0963(3) 1.2891(2) 0.38406(7) 0.0565(5) Uani 1 1 d . . . H37A H -0.0096 1.3827 0.3826 0.068 Uiso 1 1 calc R . . C38 C 0.1012(2) 1.1802(2) 0.41939(7) 0.0477(4) Uani 1 1 d . . . H38A H -0.0006 1.2004 0.4418 0.057 Uiso 1 1 calc R . . C39 C 0.4831(2) 0.3990(2) 0.21915(6) 0.0418(4) Uani 1 1 d . . . C40 C 0.5487(2) 0.3586(2) 0.17089(6) 0.0476(5) Uani 1 1 d . . . H40A H 0.6742 0.3128 0.1615 0.057 Uiso 1 1 calc R . . C41 C 0.4297(2) 0.3857(2) 0.13680(6) 0.0463(4) Uani 1 1 d . . . H41A H 0.4765 0.3571 0.1047 0.056 Uiso 1 1 calc R . . C42 C 0.2420(2) 0.45451(19) 0.14903(6) 0.0378(4) Uani 1 1 d . . . C43 C 0.1780(2) 0.4988(2) 0.19682(6) 0.0450(4) Uani 1 1 d . . . H43A H 0.0525 0.5477 0.2060 0.054 Uiso 1 1 calc R . . C44 C 0.2966(2) 0.4721(2) 0.23146(6) 0.0477(5) Uani 1 1 d . . . H44A H 0.2497 0.5040 0.2634 0.057 Uiso 1 1 calc R . . C45 C 0.5836(2) 0.4839(2) 0.28943(6) 0.0404(4) Uani 1 1 d . . . C46 C 0.5493(2) 0.6372(2) 0.27554(6) 0.0461(4) Uani 1 1 d . . . H46A H 0.5340 0.6638 0.2435 0.055 Uiso 1 1 calc R . . C47 C 0.5373(2) 0.7522(2) 0.30837(6) 0.0430(4) Uani 1 1 d . . . H47A H 0.5145 0.8549 0.2980 0.052 Uiso 1 1 calc R . . C48 C 0.5587(2) 0.71723(19) 0.35654(5) 0.0342(4) Uani 1 1 d . . . C49 C 0.5893(2) 0.5631(2) 0.37032(6) 0.0393(4) Uani 1 1 d . . . H49A H 0.6028 0.5365 0.4025 0.047 Uiso 1 1 calc R . . C50 C 0.6001(2) 0.4486(2) 0.33764(6) 0.0429(4) Uani 1 1 d . . . H50A H 0.6186 0.3468 0.3480 0.051 Uiso 1 1 calc R . . C51 C 0.7603(2) 0.2142(2) 0.25320(6) 0.0450(4) Uani 1 1 d . . . C52 C 0.9219(3) 0.2010(2) 0.26880(7) 0.0593(5) Uani 1 1 d . . . H52A H 0.9301 0.2911 0.2806 0.071 Uiso 1 1 calc R . . C53 C 1.0705(3) 0.0543(3) 0.26675(8) 0.0750(7) Uani 1 1 d . . . H53A H 1.1779 0.0460 0.2779 0.090 Uiso 1 1 calc R . . C54 C 1.0631(3) -0.0791(3) 0.24874(8) 0.0757(7) Uani 1 1 d . . . H54A H 1.1648 -0.1772 0.2471 0.091 Uiso 1 1 calc R . . C55 C 0.9047(3) -0.0666(2) 0.23319(7) 0.0669(6) Uani 1 1 d . . . H55A H 0.8992 -0.1569 0.2206 0.080 Uiso 1 1 calc R . . C56 C 0.7526(3) 0.0774(2) 0.23581(6) 0.0537(5) Uani 1 1 d . . . H56A H 0.6444 0.0831 0.2259 0.064 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.0538(9) 0.0441(9) 0.0460(9) -0.0130(7) -0.0260(7) -0.0046(7) C1 0.0576(12) 0.0567(13) 0.0543(11) 0.0095(9) -0.0295(9) -0.0327(10) C2 0.0755(15) 0.0555(13) 0.0712(14) 0.0136(11) -0.0395(12) -0.0345(12) C3 0.0686(15) 0.0525(13) 0.0788(15) -0.0050(12) -0.0364(12) -0.0119(11) C4 0.0541(12) 0.0660(14) 0.0634(13) -0.0014(11) -0.0173(10) -0.0138(11) C5 0.0482(11) 0.0571(12) 0.0487(11) 0.0017(9) -0.0132(9) -0.0191(10) C6 0.0466(10) 0.0524(11) 0.0396(9) 0.0023(8) -0.0179(8) -0.0253(9) C7 0.0410(9) 0.0520(11) 0.0324(9) 0.0019(7) -0.0115(7) -0.0233(8) C8 0.0447(10) 0.0666(13) 0.0364(9) 0.0069(9) -0.0169(8) -0.0321(9) C9 0.0583(12) 0.0736(14) 0.0462(11) 0.0149(10) -0.0239(9) -0.0437(11) C10 0.0779(15) 0.0998(18) 0.0586(13) 0.0310(13) -0.0326(12) -0.0626(14) C11 0.0729(15) 0.135(2) 0.0398(11) 0.0144(14) -0.0116(11) -0.0698(16) C12 0.0601(13) 0.110(2) 0.0397(11) -0.0023(12) -0.0076(9) -0.0481(13) C13 0.0442(10) 0.0809(14) 0.0357(10) -0.0060(9) -0.0104(8) -0.0319(10) C14 0.0401(10) 0.0653(13) 0.0442(10) -0.0062(9) -0.0121(8) -0.0250(9) C15 0.0389(9) 0.0549(11) 0.0408(9) -0.0012(8) -0.0132(7) -0.0234(8) C16 0.0493(11) 0.0631(13) 0.0539(11) 0.0014(10) -0.0103(9) -0.0300(10) C17 0.0677(14) 0.0631(15) 0.0864(16) 0.0027(12) -0.0177(12) -0.0383(12) C18 0.0663(14) 0.0620(14) 0.0932(18) -0.0099(13) -0.0202(13) -0.0329(12) C19 0.0493(12) 0.0741(15) 0.0636(13) -0.0241(12) -0.0130(10) -0.0207(11) C20 0.0407(9) 0.0358(9) 0.0451(10) -0.0077(8) -0.0100(7) -0.0168(8) C21 0.0432(10) 0.0432(11) 0.0582(11) -0.0048(9) -0.0163(9) -0.0160(8) C22 0.0362(10) 0.0570(13) 0.0802(15) -0.0086(11) -0.0143(10) -0.0190(9) C23 0.0418(11) 0.0747(15) 0.0734(14) -0.0047(11) -0.0006(10) -0.0322(10) C24 0.0455(10) 0.0661(13) 0.0501(11) -0.0008(9) -0.0047(8) -0.0291(10) C25 0.0372(9) 0.0395(10) 0.0427(9) -0.0078(8) -0.0048(7) -0.0185(8) C26 0.0344(8) 0.0408(10) 0.0341(8) -0.0036(7) -0.0046(7) -0.0188(7) C27 0.0388(9) 0.0369(9) 0.0335(8) -0.0046(7) -0.0072(7) -0.0205(8) C28 0.0435(9) 0.0360(9) 0.0391(9) -0.0037(7) -0.0092(7) -0.0194(8) C29 0.0561(11) 0.0479(11) 0.0402(10) 0.0025(8) -0.0141(8) -0.0256(9) C30 0.0604(12) 0.0560(12) 0.0359(9) -0.0008(8) -0.0037(8) -0.0336(10) C31 0.0423(10) 0.0490(11) 0.0433(10) -0.0081(8) 0.0012(8) -0.0252(8) C32 0.0384(9) 0.0422(10) 0.0379(9) -0.0060(7) -0.0042(7) -0.0233(8) C33 0.0373(9) 0.0401(10) 0.0423(9) -0.0055(7) -0.0090(7) -0.0197(8) C34 0.0410(9) 0.0391(10) 0.0372(9) -0.0028(7) -0.0093(7) -0.0210(8) C35 0.0578(11) 0.0494(11) 0.0425(10) 0.0010(8) -0.0079(8) -0.0282(10) C36 0.0750(14) 0.0465(12) 0.0577(12) 0.0114(9) -0.0222(11) -0.0269(11) C37 0.0545(12) 0.0442(11) 0.0666(13) -0.0002(10) -0.0219(10) -0.0130(9) C38 0.0394(10) 0.0474(11) 0.0563(11) -0.0079(9) -0.0092(8) -0.0168(9) C39 0.0475(10) 0.0384(10) 0.0386(9) -0.0038(7) -0.0169(8) -0.0140(8) C40 0.0387(10) 0.0654(13) 0.0404(10) -0.0052(9) -0.0091(8) -0.0223(9) C41 0.0472(10) 0.0658(12) 0.0302(9) -0.0048(8) -0.0069(7) -0.0272(9) C42 0.0420(9) 0.0400(10) 0.0349(9) 0.0022(7) -0.0107(7) -0.0193(8) C43 0.0395(9) 0.0511(11) 0.0378(9) -0.0010(8) -0.0096(7) -0.0115(8) C44 0.0520(11) 0.0498(11) 0.0319(9) -0.0044(8) -0.0104(8) -0.0106(9) C45 0.0382(9) 0.0429(10) 0.0365(9) -0.0080(8) -0.0124(7) -0.0112(8) C46 0.0540(11) 0.0499(11) 0.0296(9) -0.0004(8) -0.0096(8) -0.0161(9) C47 0.0523(11) 0.0402(10) 0.0359(9) 0.0012(8) -0.0081(8) -0.0181(8) C48 0.0287(8) 0.0415(10) 0.0337(8) -0.0039(7) -0.0041(6) -0.0155(7) C49 0.0455(10) 0.0450(10) 0.0290(8) -0.0005(7) -0.0099(7) -0.0192(8) C50 0.0530(11) 0.0394(10) 0.0392(9) 0.0006(8) -0.0155(8) -0.0199(8) C51 0.0486(10) 0.0444(11) 0.0342(9) -0.0049(8) -0.0127(8) -0.0099(9) C52 0.0525(12) 0.0586(13) 0.0602(12) -0.0101(10) -0.0207(9) -0.0131(10) C53 0.0546(13) 0.0738(16) 0.0795(15) -0.0125(13) -0.0272(11) -0.0052(12) C54 0.0697(15) 0.0561(14) 0.0717(15) -0.0064(11) -0.0204(12) 0.0054(11) C55 0.0819(16) 0.0443(12) 0.0626(13) -0.0092(10) -0.0172(12) -0.0123(11) C56 0.0586(12) 0.0498(12) 0.0486(11) -0.0068(9) -0.0152(9) -0.0165(10) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C51 1.415(2) . ? N1 C45 1.422(2) . ? N1 C39 1.425(2) . ? C1 C2 1.378(3) . ? C1 C6 1.422(2) . ? C1 C9 1.488(3) . ? C2 C3 1.386(3) . ? C2 H2A 0.9300 . ? C3 C4 1.377(3) . ? C3 H3A 0.9300 . ? C4 C5 1.385(3) . ? C4 H4A 0.9300 . ? C5 C6 1.378(2) . ? C5 H5A 0.9300 . ? C6 C7 1.531(2) . ? C7 C8 1.494(2) . ? C7 C15 1.537(2) . ? C7 C42 1.547(2) . ? C8 C9 1.375(3) . ? C8 C13 1.377(3) . ? C9 C10 1.403(3) . ? C10 C11 1.392(3) . ? C10 H10A 0.9300 . ? C11 C12 1.385(3) . ? C11 H11A 0.9300 . ? C12 C13 1.392(3) . ? C12 H12A 0.9300 . ? C13 C14 1.475(3) . ? C14 C19 1.394(3) . ? C14 C15 1.412(2) . ? C15 C16 1.380(2) . ? C16 C17 1.387(3) . ? C16 H16A 0.9300 . ? C17 C18 1.368(3) . ? C17 H17A 0.9300 . ? C18 C19 1.373(3) . ? C18 H18A 0.9300 . ? C19 H19A 0.9300 . ? C20 C21 1.388(2) . ? C20 C25 1.415(2) . ? C20 C28 1.485(2) . ? C21 C22 1.380(3) . ? C21 H21A 0.9300 . ? C22 C23 1.379(3) . ? C22 H22A 0.9300 . ? C23 C24 1.384(3) . ? C23 H23A 0.9300 . ? C24 C25 1.378(2) . ? C24 H24A 0.9300 . ? C25 C26 1.533(2) . ? C26 C27 1.491(2) . ? C26 C34 1.532(2) . ? C26 C48 1.547(2) . ? C27 C28 1.374(2) . ? C27 C32 1.378(2) . ? C28 C29 1.396(2) . ? C29 C30 1.390(2) . ? C29 H29A 0.9300 . ? C30 C31 1.393(2) . ? C30 H30A 0.9300 . ? C31 C32 1.389(2) . ? C31 H31A 0.9300 . ? C32 C33 1.486(2) . ? C33 C38 1.383(2) . ? C33 C34 1.418(2) . ? C34 C35 1.379(2) . ? C35 C36 1.388(3) . ? C35 H35A 0.9300 . ? C36 C37 1.374(3) . ? C36 H36A 0.9300 . ? C37 C38 1.382(3) . ? C37 H37A 0.9300 . ? C38 H38A 0.9300 . ? C39 C44 1.376(2) . ? C39 C40 1.387(2) . ? C40 C41 1.376(2) . ? C40 H40A 0.9300 . ? C41 C42 1.384(2) . ? C41 H41A 0.9300 . ? C42 C43 1.378(2) . ? C43 C44 1.385(2) . ? C43 H43A 0.9300 . ? C44 H44A 0.9300 . ? C45 C46 1.375(2) . ? C45 C50 1.383(2) . ? C46 C47 1.379(2) . ? C46 H46A 0.9300 . ? C47 C48 1.386(2) . ? C47 H47A 0.9300 . ? C48 C49 1.387(2) . ? C49 C50 1.377(2) . ? C49 H49A 0.9300 . ? C50 H50A 0.9300 . ? C51 C52 1.383(3) . ? C51 C56 1.388(3) . ? C52 C53 1.378(3) . ? C52 H52A 0.9300 . ? C53 C54 1.364(3) . ? C53 H53A 0.9300 . ? C54 C55 1.361(3) . ? C54 H54A 0.9300 . ? C55 C56 1.375(3) . ? C55 H55A 0.9300 . ? C56 H56A 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C51 N1 C45 119.78(13) . . ? C51 N1 C39 119.91(13) . . ? C45 N1 C39 119.91(13) . . ? C2 C1 C6 119.64(19) . . ? C2 C1 C9 131.41(18) . . ? C6 C1 C9 108.12(16) . . ? C1 C2 C3 119.4(2) . . ? C1 C2 H2A 120.3 . . ? C3 C2 H2A 120.3 . . ? C4 C3 C2 120.9(2) . . ? C4 C3 H3A 119.6 . . ? C2 C3 H3A 119.6 . . ? C3 C4 C5 120.5(2) . . ? C3 C4 H4A 119.8 . . ? C5 C4 H4A 119.8 . . ? C6 C5 C4 119.54(19) . . ? C6 C5 H5A 120.2 . . ? C4 C5 H5A 120.2 . . ? C5 C6 C1 119.91(17) . . ? C5 C6 C7 130.82(16) . . ? C1 C6 C7 109.26(15) . . ? C8 C7 C6 99.18(14) . . ? C8 C7 C15 99.11(13) . . ? C6 C7 C15 127.35(14) . . ? C8 C7 C42 112.74(13) . . ? C6 C7 C42 110.97(13) . . ? C15 C7 C42 106.39(13) . . ? C9 C8 C13 125.30(17) . . ? C9 C8 C7 114.54(17) . . ? C13 C8 C7 115.09(17) . . ? C8 C9 C10 115.9(2) . . ? C8 C9 C1 105.68(16) . . ? C10 C9 C1 134.98(19) . . ? C11 C10 C9 118.2(2) . . ? C11 C10 H10A 120.9 . . ? C9 C10 H10A 120.9 . . ? C12 C11 C10 123.4(2) . . ? C12 C11 H11A 118.3 . . ? C10 C11 H11A 118.3 . . ? C11 C12 C13 118.0(2) . . ? C11 C12 H12A 121.0 . . ? C13 C12 H12A 121.0 . . ? C8 C13 C12 116.7(2) . . ? C8 C13 C14 105.79(15) . . ? C12 C13 C14 135.28(19) . . ? C19 C14 C15 119.20(18) . . ? C19 C14 C13 131.76(18) . . ? C15 C14 C13 108.86(16) . . ? C16 C15 C14 120.04(18) . . ? C16 C15 C7 129.53(16) . . ? C14 C15 C7 109.94(15) . . ? C15 C16 C17 119.38(19) . . ? C15 C16 H16A 120.3 . . ? C17 C16 H16A 120.3 . . ? C18 C17 C16 120.7(2) . . ? C18 C17 H17A 119.7 . . ? C16 C17 H17A 119.7 . . ? C17 C18 C19 121.0(2) . . ? C17 C18 H18A 119.5 . . ? C19 C18 H18A 119.5 . . ? C18 C19 C14 119.64(19) . . ? C18 C19 H19A 120.2 . . ? C14 C19 H19A 120.2 . . ? C21 C20 C25 119.39(16) . . ? C21 C20 C28 131.50(16) . . ? C25 C20 C28 108.74(14) . . ? C22 C21 C20 119.36(18) . . ? C22 C21 H21A 120.3 . . ? C20 C21 H21A 120.3 . . ? C23 C22 C21 120.98(17) . . ? C23 C22 H22A 119.5 . . ? C21 C22 H22A 119.5 . . ? C22 C23 C24 120.62(18) . . ? C22 C23 H23A 119.7 . . ? C24 C23 H23A 119.7 . . ? C25 C24 C23 119.21(18) . . ? C25 C24 H24A 120.4 . . ? C23 C24 H24A 120.4 . . ? C24 C25 C20 120.43(16) . . ? C24 C25 C26 129.62(16) . . ? C20 C25 C26 109.68(13) . . ? C27 C26 C34 98.98(12) . . ? C27 C26 C25 99.27(12) . . ? C34 C26 C25 127.28(13) . . ? C27 C26 C48 112.68(13) . . ? C34 C26 C48 110.62(12) . . ? C25 C26 C48 106.87(12) . . ? C28 C27 C32 124.92(15) . . ? C28 C27 C26 115.27(14) . . ? C32 C27 C26 115.06(14) . . ? C27 C28 C29 116.65(15) . . ? C27 C28 C20 105.36(14) . . ? C29 C28 C20 135.69(15) . . ? C30 C29 C28 118.06(16) . . ? C30 C29 H29A 121.0 . . ? C28 C29 H29A 121.0 . . ? C29 C30 C31 123.00(16) . . ? C29 C30 H30A 118.5 . . ? C31 C30 H30A 118.5 . . ? C32 C31 C30 118.41(16) . . ? C32 C31 H31A 120.8 . . ? C30 C31 H31A 120.8 . . ? C27 C32 C31 116.53(15) . . ? C27 C32 C33 105.22(13) . . ? C31 C32 C33 135.23(15) . . ? C38 C33 C34 119.98(16) . . ? C38 C33 C32 130.82(15) . . ? C34 C33 C32 108.49(14) . . ? C35 C34 C33 119.68(16) . . ? C35 C34 C26 130.90(15) . . ? C33 C34 C26 109.41(14) . . ? C34 C35 C36 119.17(17) . . ? C34 C35 H35A 120.4 . . ? C36 C35 H35A 120.4 . . ? C37 C36 C35 121.18(18) . . ? C37 C36 H36A 119.4 . . ? C35 C36 H36A 119.4 . . ? C36 C37 C38 120.43(18) . . ? C36 C37 H37A 119.8 . . ? C38 C37 H37A 119.8 . . ? C37 C38 C33 119.44(17) . . ? C37 C38 H38A 120.3 . . ? C33 C38 H38A 120.3 . . ? C44 C39 C40 118.20(15) . . ? C44 C39 N1 120.94(15) . . ? C40 C39 N1 120.85(15) . . ? C41 C40 C39 120.47(16) . . ? C41 C40 H40A 119.8 . . ? C39 C40 H40A 119.8 . . ? C40 C41 C42 121.76(15) . . ? C40 C41 H41A 119.1 . . ? C42 C41 H41A 119.1 . . ? C43 C42 C41 117.31(15) . . ? C43 C42 C7 122.82(14) . . ? C41 C42 C7 119.70(14) . . ? C42 C43 C44 121.41(16) . . ? C42 C43 H43A 119.3 . . ? C44 C43 H43A 119.3 . . ? C39 C44 C43 120.79(15) . . ? C39 C44 H44A 119.6 . . ? C43 C44 H44A 119.6 . . ? C46 C45 C50 118.32(15) . . ? C46 C45 N1 121.07(15) . . ? C50 C45 N1 120.60(16) . . ? C45 C46 C47 121.14(16) . . ? C45 C46 H46A 119.4 . . ? C47 C46 H46A 119.4 . . ? C46 C47 C48 121.13(16) . . ? C46 C47 H47A 119.4 . . ? C48 C47 H47A 119.4 . . ? C47 C48 C49 117.20(15) . . ? C47 C48 C26 122.10(15) . . ? C49 C48 C26 120.62(14) . . ? C50 C49 C48 121.70(15) . . ? C50 C49 H49A 119.2 . . ? C48 C49 H49A 119.2 . . ? C49 C50 C45 120.46(16) . . ? C49 C50 H50A 119.8 . . ? C45 C50 H50A 119.8 . . ? C52 C51 C56 118.58(17) . . ? C52 C51 N1 121.06(17) . . ? C56 C51 N1 120.36(16) . . ? C53 C52 C51 119.9(2) . . ? C53 C52 H52A 120.1 . . ? C51 C52 H52A 120.1 . . ? C54 C53 C52 121.3(2) . . ? C54 C53 H53A 119.4 . . ? C52 C53 H53A 119.4 . . ? C55 C54 C53 119.1(2) . . ? C55 C54 H54A 120.5 . . ? C53 C54 H54A 120.5 . . ? C54 C55 C56 121.1(2) . . ? C54 C55 H55A 119.5 . . ? C56 C55 H55A 119.5 . . ? C55 C56 C51 120.12(19) . . ? C55 C56 H56A 119.9 . . ? C51 C56 H56A 119.9 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C1 C2 C3 -3.0(3) . . . . ? C9 C1 C2 C3 165.26(18) . . . . ? C1 C2 C3 C4 -0.1(3) . . . . ? C2 C3 C4 C5 2.7(3) . . . . ? C3 C4 C5 C6 -2.1(3) . . . . ? C4 C5 C6 C1 -1.0(3) . . . . ? C4 C5 C6 C7 177.69(17) . . . . ? C2 C1 C6 C5 3.5(3) . . . . ? C9 C1 C6 C5 -167.20(15) . . . . ? C2 C1 C6 C7 -175.38(15) . . . . ? C9 C1 C6 C7 13.87(18) . . . . ? C5 C6 C7 C8 163.69(18) . . . . ? C1 C6 C7 C8 -17.54(17) . . . . ? C5 C6 C7 C15 54.7(3) . . . . ? C1 C6 C7 C15 -126.51(17) . . . . ? C5 C6 C7 C42 -77.5(2) . . . . ? C1 C6 C7 C42 101.23(16) . . . . ? C6 C7 C8 C9 16.21(18) . . . . ? C15 C7 C8 C9 146.63(15) . . . . ? C42 C7 C8 C9 -101.22(17) . . . . ? C6 C7 C8 C13 -140.02(15) . . . . ? C15 C7 C8 C13 -9.60(18) . . . . ? C42 C7 C8 C13 102.54(17) . . . . ? C13 C8 C9 C10 -17.6(3) . . . . ? C7 C8 C9 C10 -171.02(15) . . . . ? C13 C8 C9 C1 144.61(17) . . . . ? C7 C8 C9 C1 -8.83(19) . . . . ? C2 C1 C9 C8 -172.73(19) . . . . ? C6 C1 C9 C8 -3.47(19) . . . . ? C2 C1 C9 C10 -15.6(4) . . . . ? C6 C1 C9 C10 153.6(2) . . . . ? C8 C9 C10 C11 5.3(3) . . . . ? C1 C9 C10 C11 -150.1(2) . . . . ? C9 C10 C11 C12 6.1(3) . . . . ? C10 C11 C12 C13 -6.5(3) . . . . ? C9 C8 C13 C12 17.3(3) . . . . ? C7 C8 C13 C12 170.64(15) . . . . ? C9 C8 C13 C14 -148.39(17) . . . . ? C7 C8 C13 C14 4.92(19) . . . . ? C11 C12 C13 C8 -4.6(3) . . . . ? C11 C12 C13 C14 155.7(2) . . . . ? C8 C13 C14 C19 177.61(18) . . . . ? C12 C13 C14 C19 15.9(3) . . . . ? C8 C13 C14 C15 2.70(18) . . . . ? C12 C13 C14 C15 -159.1(2) . . . . ? C19 C14 C15 C16 2.7(2) . . . . ? C13 C14 C15 C16 178.36(15) . . . . ? C19 C14 C15 C7 175.42(15) . . . . ? C13 C14 C15 C7 -8.93(18) . . . . ? C8 C7 C15 C16 -177.39(17) . . . . ? C6 C7 C15 C16 -68.4(2) . . . . ? C42 C7 C15 C16 65.5(2) . . . . ? C8 C7 C15 C14 10.80(16) . . . . ? C6 C7 C15 C14 119.80(17) . . . . ? C42 C7 C15 C14 -106.28(15) . . . . ? C14 C15 C16 C17 -2.8(3) . . . . ? C7 C15 C16 C17 -173.93(17) . . . . ? C15 C16 C17 C18 1.4(3) . . . . ? C16 C17 C18 C19 0.2(3) . . . . ? C17 C18 C19 C14 -0.4(3) . . . . ? C15 C14 C19 C18 -1.1(3) . . . . ? C13 C14 C19 C18 -175.59(18) . . . . ? C25 C20 C21 C22 -0.6(3) . . . . ? C28 C20 C21 C22 -172.73(17) . . . . ? C20 C21 C22 C23 0.1(3) . . . . ? C21 C22 C23 C24 -0.5(3) . . . . ? C22 C23 C24 C25 1.4(3) . . . . ? C23 C24 C25 C20 -1.9(3) . . . . ? C23 C24 C25 C26 -175.20(17) . . . . ? C21 C20 C25 C24 1.5(2) . . . . ? C28 C20 C25 C24 175.29(15) . . . . ? C21 C20 C25 C26 176.04(14) . . . . ? C28 C20 C25 C26 -10.20(18) . . . . ? C24 C25 C26 C27 -173.45(17) . . . . ? C20 C25 C26 C27 12.69(16) . . . . ? C24 C25 C26 C34 -64.6(2) . . . . ? C20 C25 C26 C34 121.55(16) . . . . ? C24 C25 C26 C48 69.3(2) . . . . ? C20 C25 C26 C48 -104.54(15) . . . . ? C34 C26 C27 C28 -141.98(14) . . . . ? C25 C26 C27 C28 -11.65(17) . . . . ? C48 C26 C27 C28 101.11(16) . . . . ? C34 C26 C27 C32 14.88(17) . . . . ? C25 C26 C27 C32 145.21(14) . . . . ? C48 C26 C27 C32 -102.03(16) . . . . ? C32 C27 C28 C29 17.5(2) . . . . ? C26 C27 C28 C29 171.77(14) . . . . ? C32 C27 C28 C20 -148.01(15) . . . . ? C26 C27 C28 C20 6.25(18) . . . . ? C21 C20 C28 C27 175.46(18) . . . . ? C25 C20 C28 C27 2.72(18) . . . . ? C21 C20 C28 C29 14.1(3) . . . . ? C25 C20 C28 C29 -158.61(19) . . . . ? C27 C28 C29 C30 -5.5(2) . . . . ? C20 C28 C29 C30 154.34(18) . . . . ? C28 C29 C30 C31 -6.2(3) . . . . ? C29 C30 C31 C32 7.0(3) . . . . ? C28 C27 C32 C31 -16.7(2) . . . . ? C26 C27 C32 C31 -171.01(14) . . . . ? C28 C27 C32 C33 146.66(16) . . . . ? C26 C27 C32 C33 -7.65(18) . . . . ? C30 C31 C32 C27 3.9(2) . . . . ? C30 C31 C32 C33 -152.99(18) . . . . ? C27 C32 C33 C38 -174.06(17) . . . . ? C31 C32 C33 C38 -15.4(3) . . . . ? C27 C32 C33 C34 -4.00(17) . . . . ? C31 C32 C33 C34 154.67(18) . . . . ? C38 C33 C34 C35 3.7(2) . . . . ? C32 C33 C34 C35 -167.67(14) . . . . ? C38 C33 C34 C26 -175.09(14) . . . . ? C32 C33 C34 C26 13.58(17) . . . . ? C27 C26 C34 C35 164.87(17) . . . . ? C25 C26 C34 C35 55.9(3) . . . . ? C48 C26 C34 C35 -76.7(2) . . . . ? C27 C26 C34 C33 -16.57(16) . . . . ? C25 C26 C34 C33 -125.55(16) . . . . ? C48 C26 C34 C33 101.89(15) . . . . ? C33 C34 C35 C36 -1.4(2) . . . . ? C26 C34 C35 C36 177.04(16) . . . . ? C34 C35 C36 C37 -1.8(3) . . . . ? C35 C36 C37 C38 2.7(3) . . . . ? C36 C37 C38 C33 -0.4(3) . . . . ? C34 C33 C38 C37 -2.7(2) . . . . ? C32 C33 C38 C37 166.36(17) . . . . ? C51 N1 C39 C44 137.46(18) . . . . ? C45 N1 C39 C44 -49.8(2) . . . . ? C51 N1 C39 C40 -41.5(3) . . . . ? C45 N1 C39 C40 131.30(18) . . . . ? C44 C39 C40 C41 -2.5(3) . . . . ? N1 C39 C40 C41 176.50(17) . . . . ? C39 C40 C41 C42 0.4(3) . . . . ? C40 C41 C42 C43 1.6(3) . . . . ? C40 C41 C42 C7 -173.78(16) . . . . ? C8 C7 C42 C43 149.81(17) . . . . ? C6 C7 C42 C43 39.6(2) . . . . ? C15 C7 C42 C43 -102.60(18) . . . . ? C8 C7 C42 C41 -35.1(2) . . . . ? C6 C7 C42 C41 -145.36(16) . . . . ? C15 C7 C42 C41 72.46(18) . . . . ? C41 C42 C43 C44 -1.5(3) . . . . ? C7 C42 C43 C44 173.66(16) . . . . ? C40 C39 C44 C43 2.5(3) . . . . ? N1 C39 C44 C43 -176.46(17) . . . . ? C42 C43 C44 C39 -0.5(3) . . . . ? C51 N1 C45 C46 128.67(18) . . . . ? C39 N1 C45 C46 -44.1(2) . . . . ? C51 N1 C45 C50 -50.0(2) . . . . ? C39 N1 C45 C50 137.21(17) . . . . ? C50 C45 C46 C47 2.0(3) . . . . ? N1 C45 C46 C47 -176.69(16) . . . . ? C45 C46 C47 C48 -0.2(3) . . . . ? C46 C47 C48 C49 -1.1(2) . . . . ? C46 C47 C48 C26 175.58(15) . . . . ? C27 C26 C48 C47 151.74(15) . . . . ? C34 C26 C48 C47 41.98(19) . . . . ? C25 C26 C48 C47 -100.25(17) . . . . ? C27 C26 C48 C49 -31.68(19) . . . . ? C34 C26 C48 C49 -141.44(15) . . . . ? C25 C26 C48 C49 76.33(17) . . . . ? C47 C48 C49 C50 0.7(2) . . . . ? C26 C48 C49 C50 -176.06(14) . . . . ? C48 C49 C50 C45 1.1(3) . . . . ? C46 C45 C50 C49 -2.4(2) . . . . ? N1 C45 C50 C49 176.29(15) . . . . ? C45 N1 C51 C52 -25.8(3) . . . . ? C39 N1 C51 C52 146.98(18) . . . . ? C45 N1 C51 C56 153.83(17) . . . . ? C39 N1 C51 C56 -33.4(3) . . . . ? C56 C51 C52 C53 0.1(3) . . . . ? N1 C51 C52 C53 179.73(18) . . . . ? C51 C52 C53 C54 1.2(3) . . . . ? C52 C53 C54 C55 -0.9(4) . . . . ? C53 C54 C55 C56 -0.6(3) . . . . ? C54 C55 C56 C51 1.9(3) . . . . ? C52 C51 C56 C55 -1.6(3) . . . . ? N1 C51 C56 C55 178.74(17) . . . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.166 _refine_diff_density_min -0.159 _refine_diff_density_rms 0.031