Supplementary Material (ESI) for Chemical Communications This journal is © The Royal Society of Chemistry 2002 data_0211 _database_code_CSD 190316 _journal_coden_Cambridge 182 loop_ _publ_author_name 'Zhi-qiang Liu' 'Qi Fang' 'Dong Wang' 'Gang Xue' 'Wen-tao Yu' 'Zong-shu Shao' 'Min-hua Jiang ' _publ_contact_author_name 'Prof Qi Fang' _publ_contact_author_address ; State Key Laboratory of Crystal Materials Shanda South Road 27# Jinan 250100 CHINA ; _publ_contact_author_email 'fangqi@icm.sdu.edu.cn' _journal_name_full 'Chemical communication' _publ_section_title ; Trivalent Boron as Acceptor in D-pi-A Chromophores: Synthesis, Structure and Fluorescences Excited by Single & Two-Photon ; _audit_creation_method SHELXL-97 _chemical_name_systematic ; {2-[4'-(N,N-dimethylamino)styryl]-thiophen-5-yl}-bis- (2,4,6-trimethyl-phenyl)-borane ; _chemical_name_common ; {2-[4'-(N,N-dimethylamino)styryl]-thiophen-5-yl}-dimesityl-borane ; _chemical_melting_point '436-437 K ' _chemical_formula_moiety 'C32 H36 B N S' _chemical_formula_sum 'C32 H36 B N S' _chemical_formula_weight 477.49 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' 'B' 'B' 0.0013 0.0007 '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' 'S' 'S' 0.1246 0.1234 '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 8.0588(12) _cell_length_b 10.4341(14) _cell_length_c 17.705(3) _cell_angle_alpha 74.182(12) _cell_angle_beta 86.993(9) _cell_angle_gamma 79.471(11) _cell_volume 1408.2(4) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 47 _cell_measurement_theta_min 5.208 _cell_measurement_theta_max 12.474 _exptl_crystal_description plate _exptl_crystal_colour ORANGE _exptl_crystal_size_max 0.44 _exptl_crystal_size_mid 0.4 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.126 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 512 _exptl_absorpt_coefficient_mu 0.135 _exptl_absorpt_correction_type PSI-SCAN _exptl_absorpt_correction_T_min 0.332 _exptl_absorpt_correction_T_max 0.349 _exptl_absorpt_process_details 'BRUKER XSCAN(BRUKER,1996)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 'BRUKER P4' _diffrn_measurement_method \q/2\q _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count 97 _diffrn_standards_interval_time ? _diffrn_standards_decay_% 2 _diffrn_reflns_number 6043 _diffrn_reflns_av_R_equivalents 0.0259 _diffrn_reflns_av_sigmaI/netI 0.0604 _diffrn_reflns_limit_h_min -1 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.06 _diffrn_reflns_theta_max 25.00 _reflns_number_total 4905 _reflns_number_gt 2893 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'BRUKER XCAN(BRUKER,1996)' _computing_cell_refinement 'BRUKER XCAN(BRUKER,1996)' _computing_data_reduction 'BRUKER XCAN(BRUKER,1996)' _computing_structure_solution 'BRUKER SHELXTL(BRUKER,1997)' _computing_structure_refinement 'BRUKER SHELXTL(BRUKER,1997)' _computing_molecular_graphics 'BRUKER SHELXTL(BRUKER,1997)' _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^)+(0.0824P)^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 mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.006(2) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 4905 _refine_ls_number_parameters 317 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1084 _refine_ls_R_factor_gt 0.0582 _refine_ls_wR_factor_ref 0.1841 _refine_ls_wR_factor_gt 0.1602 _refine_ls_goodness_of_fit_ref 1.140 _refine_ls_restrained_S_all 1.140 _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 S1 S 0.13840(12) 0.13701(8) 0.28313(5) 0.0577(3) Uani 1 1 d . . . N1 N -0.3707(4) 0.6718(3) 0.56744(16) 0.0750(9) Uani 1 1 d . . . B1 B 0.3010(5) -0.0504(3) 0.1987(2) 0.0490(9) Uani 1 1 d . . . C1 C -0.4281(6) 0.6232(4) 0.6471(2) 0.0851(12) Uani 1 1 d . . . H1A H -0.4075 0.5261 0.6622 0.128 Uiso 1 1 calc R . . H1B H -0.5468 0.6561 0.6504 0.128 Uiso 1 1 calc R . . H1C H -0.3681 0.6553 0.6817 0.128 Uiso 1 1 calc R . . C2 C -0.3891(6) 0.8150(3) 0.5338(2) 0.0837(12) Uani 1 1 d . . . H2A H -0.3438 0.8328 0.4815 0.126 Uiso 1 1 calc R . . H2B H -0.3293 0.8534 0.5652 0.126 Uiso 1 1 calc R . . H2C H -0.5065 0.8548 0.5322 0.126 Uiso 1 1 calc R . . C3 C -0.3028(4) 0.5823(3) 0.52445(18) 0.0571(8) Uani 1 1 d . . . C4 C -0.3084(5) 0.4442(3) 0.55209(19) 0.0618(9) Uani 1 1 d . . . H4A H -0.3592 0.4117 0.6002 0.074 Uiso 1 1 calc R . . C5 C -0.2401(4) 0.3563(3) 0.50907(19) 0.0610(9) Uani 1 1 d . . . H5A H -0.2491 0.2654 0.5280 0.073 Uiso 1 1 calc R . . C6 C -0.1572(4) 0.3988(3) 0.43762(18) 0.0564(8) Uani 1 1 d . . . C7 C -0.1518(5) 0.5351(3) 0.4112(2) 0.0655(9) Uani 1 1 d . . . H7A H -0.0983 0.5672 0.3638 0.079 Uiso 1 1 calc R . . C8 C -0.2229(5) 0.6246(3) 0.45271(19) 0.0631(9) Uani 1 1 d . . . H8A H -0.2176 0.7159 0.4325 0.076 Uiso 1 1 calc R . . C9 C -0.0779(4) 0.3066(4) 0.3925(2) 0.0635(9) Uani 1 1 d . . . H9A H -0.0208 0.3451 0.3474 0.076 Uiso 1 1 calc R . . C10 C -0.0764(4) 0.1739(3) 0.40725(19) 0.0601(9) Uani 1 1 d . . . H10A H -0.1353 0.1343 0.4514 0.072 Uiso 1 1 calc R . . C11 C 0.0078(4) 0.0861(3) 0.36133(17) 0.0530(8) Uani 1 1 d . . . C12 C -0.0017(4) -0.0474(3) 0.37247(18) 0.0582(9) Uani 1 1 d . . . H12A H -0.0625 -0.0953 0.4131 0.070 Uiso 1 1 calc R . . C13 C 0.0896(4) -0.1048(3) 0.31639(18) 0.0562(8) Uani 1 1 d . . . H13A H 0.0910 -0.1937 0.3156 0.067 Uiso 1 1 calc R . . C14 C 0.1758(4) -0.0201(3) 0.26331(18) 0.0509(8) Uani 1 1 d . . . C15 C 0.4363(4) 0.0433(3) 0.16975(17) 0.0473(7) Uani 1 1 d . . . C16 C 0.5492(4) 0.0606(3) 0.22269(18) 0.0532(8) Uani 1 1 d . . . C17 C 0.6605(4) 0.1494(3) 0.1968(2) 0.0620(9) Uani 1 1 d . . . H17A H 0.7328 0.1600 0.2331 0.074 Uiso 1 1 calc R . . C18 C 0.6693(5) 0.2225(3) 0.1205(2) 0.0649(9) Uani 1 1 d . . . C19 C 0.5600(5) 0.2041(3) 0.0677(2) 0.0646(9) Uani 1 1 d . . . H19A H 0.5650 0.2511 0.0151 0.077 Uiso 1 1 calc R . . C20 C 0.4438(4) 0.1182(3) 0.09087(18) 0.0524(8) Uani 1 1 d . . . C21 C 0.7928(6) 0.3184(4) 0.0944(3) 0.1004(14) Uani 1 1 d . . . H21A H 0.8568 0.3179 0.1387 0.151 Uiso 1 1 calc R . . H21B H 0.7324 0.4081 0.0720 0.151 Uiso 1 1 calc R . . H21C H 0.8678 0.2903 0.0557 0.151 Uiso 1 1 calc R . . C22 C 0.3240(5) 0.1104(4) 0.03043(19) 0.0719(10) Uani 1 1 d . . . H22A H 0.3482 0.1680 -0.0197 0.108 Uiso 1 1 calc R . . H22B H 0.2100 0.1395 0.0454 0.108 Uiso 1 1 calc R . . H22C H 0.3373 0.0188 0.0271 0.108 Uiso 1 1 calc R . . C23 C 0.5622(5) -0.0230(4) 0.30761(18) 0.0715(10) Uani 1 1 d . . . H23A H 0.6458 0.0037 0.3339 0.107 Uiso 1 1 calc R . . H23B H 0.5940 -0.1171 0.3096 0.107 Uiso 1 1 calc R . . H23C H 0.4550 -0.0085 0.3331 0.107 Uiso 1 1 calc R . . C24 C 0.2824(4) -0.1785(3) 0.17024(17) 0.0501(8) Uani 1 1 d . . . C25 C 0.1289(4) -0.1903(3) 0.14159(19) 0.0592(9) Uani 1 1 d . . . C26 C 0.1094(5) -0.3083(4) 0.1238(2) 0.0684(10) Uani 1 1 d . . . H26A H 0.0060 -0.3134 0.1049 0.082 Uiso 1 1 calc R . . C27 C 0.2386(6) -0.4182(4) 0.1334(2) 0.0712(11) Uani 1 1 d . . . C28 C 0.3910(5) -0.4058(3) 0.1593(2) 0.0669(10) Uani 1 1 d . . . H28A H 0.4804 -0.4780 0.1650 0.080 Uiso 1 1 calc R . . C29 C 0.4166(4) -0.2884(3) 0.17736(18) 0.0580(9) Uani 1 1 d . . . C30 C 0.5879(5) -0.2866(4) 0.2075(2) 0.0783(11) Uani 1 1 d . . . H30A H 0.6621 -0.3698 0.2076 0.117 Uiso 1 1 calc R . . H30B H 0.5767 -0.2768 0.2600 0.117 Uiso 1 1 calc R . . H30C H 0.6337 -0.2121 0.1742 0.117 Uiso 1 1 calc R . . C31 C 0.2136(7) -0.5478(4) 0.1165(3) 0.1118(17) Uani 1 1 d . . . H31A H 0.3165 -0.6126 0.1270 0.168 Uiso 1 1 calc R . . H31B H 0.1834 -0.5296 0.0624 0.168 Uiso 1 1 calc R . . H31C H 0.1252 -0.5835 0.1494 0.168 Uiso 1 1 calc R . . C32 C -0.0212(5) -0.0756(4) 0.1263(2) 0.0810(12) Uani 1 1 d . . . H32A H -0.1138 -0.1041 0.1071 0.122 Uiso 1 1 calc R . . H32B H 0.0088 0.0012 0.0878 0.122 Uiso 1 1 calc R . . H32C H -0.0539 -0.0515 0.1742 0.122 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 S1 0.0662(6) 0.0545(5) 0.0564(5) -0.0176(4) 0.0086(4) -0.0194(4) N1 0.109(3) 0.0573(17) 0.0597(18) -0.0209(14) 0.0162(18) -0.0147(17) B1 0.047(2) 0.052(2) 0.0445(19) -0.0109(16) -0.0091(17) -0.0029(17) C1 0.107(3) 0.087(3) 0.065(2) -0.030(2) 0.019(2) -0.020(3) C2 0.112(3) 0.061(2) 0.081(3) -0.026(2) 0.007(2) -0.014(2) C3 0.060(2) 0.057(2) 0.0536(19) -0.0125(16) -0.0046(17) -0.0110(17) C4 0.070(2) 0.060(2) 0.0533(19) -0.0129(16) 0.0057(18) -0.0115(18) C5 0.068(2) 0.0505(18) 0.062(2) -0.0103(16) 0.0046(18) -0.0126(17) C6 0.057(2) 0.061(2) 0.0529(19) -0.0179(16) -0.0010(17) -0.0097(17) C7 0.071(2) 0.068(2) 0.057(2) -0.0126(17) 0.0102(18) -0.0219(19) C8 0.078(3) 0.0534(19) 0.060(2) -0.0140(16) 0.0049(19) -0.0206(18) C9 0.062(2) 0.069(2) 0.058(2) -0.0149(17) -0.0006(18) -0.0098(19) C10 0.059(2) 0.069(2) 0.0559(19) -0.0194(17) 0.0033(17) -0.0168(18) C11 0.0484(19) 0.065(2) 0.0461(18) -0.0148(15) -0.0001(15) -0.0119(16) C12 0.059(2) 0.058(2) 0.055(2) -0.0052(15) 0.0074(17) -0.0201(17) C13 0.062(2) 0.0526(18) 0.0577(19) -0.0165(15) 0.0043(17) -0.0184(17) C14 0.051(2) 0.0538(18) 0.0501(17) -0.0157(14) 0.0000(15) -0.0130(16) C15 0.0432(18) 0.0495(17) 0.0500(17) -0.0152(14) 0.0002(15) -0.0072(14) C16 0.051(2) 0.0586(19) 0.0521(18) -0.0188(15) 0.0004(16) -0.0098(16) C17 0.053(2) 0.073(2) 0.067(2) -0.0240(18) -0.0045(18) -0.0185(19) C18 0.059(2) 0.062(2) 0.075(2) -0.0167(18) 0.0066(19) -0.0175(18) C19 0.072(2) 0.062(2) 0.056(2) -0.0072(16) 0.0118(19) -0.0196(19) C20 0.054(2) 0.0548(18) 0.0490(18) -0.0174(14) 0.0030(16) -0.0064(16) C21 0.096(3) 0.104(3) 0.108(3) -0.018(3) 0.013(3) -0.056(3) C22 0.075(3) 0.083(3) 0.054(2) -0.0118(18) -0.0091(19) -0.014(2) C23 0.065(2) 0.093(3) 0.054(2) -0.0118(19) -0.0087(18) -0.017(2) C24 0.0481(19) 0.0501(18) 0.0531(18) -0.0145(14) 0.0050(15) -0.0111(16) C25 0.055(2) 0.063(2) 0.065(2) -0.0257(17) 0.0063(17) -0.0128(18) C26 0.069(3) 0.070(2) 0.077(2) -0.0292(19) 0.005(2) -0.028(2) C27 0.095(3) 0.058(2) 0.067(2) -0.0180(17) 0.012(2) -0.032(2) C28 0.081(3) 0.0466(19) 0.066(2) -0.0118(16) 0.013(2) -0.0025(19) C29 0.063(2) 0.0539(19) 0.0547(19) -0.0097(15) 0.0085(17) -0.0139(17) C30 0.061(2) 0.071(2) 0.095(3) -0.019(2) -0.008(2) 0.006(2) C31 0.154(5) 0.064(3) 0.131(4) -0.037(3) 0.003(4) -0.038(3) C32 0.060(2) 0.097(3) 0.100(3) -0.050(2) -0.014(2) -0.010(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 S1 C11 1.720(3) . ? S1 C14 1.739(3) . ? N1 C3 1.381(4) . ? N1 C2 1.433(4) . ? N1 C1 1.445(4) . ? B1 C14 1.544(5) . ? B1 C15 1.571(5) . ? B1 C24 1.585(4) . ? C1 H1A 0.9600 . ? C1 H1B 0.9600 . ? C1 H1C 0.9600 . ? C2 H2A 0.9600 . ? C2 H2B 0.9600 . ? C2 H2C 0.9600 . ? C3 C8 1.391(4) . ? C3 C4 1.398(4) . ? C4 C5 1.370(4) . ? C4 H4A 0.9300 . ? C5 C6 1.399(4) . ? C5 H5A 0.9300 . ? C6 C7 1.379(4) . ? C6 C9 1.454(4) . ? C7 C8 1.369(4) . ? C7 H7A 0.9300 . ? C8 H8A 0.9300 . ? C9 C10 1.335(4) . ? C9 H9A 0.9300 . ? C10 C11 1.443(4) . ? C10 H10A 0.9300 . ? C11 C12 1.368(4) . ? C12 C13 1.405(4) . ? C12 H12A 0.9300 . ? C13 C14 1.360(4) . ? C13 H13A 0.9300 . ? C15 C20 1.406(4) . ? C15 C16 1.407(4) . ? C16 C17 1.379(4) . ? C16 C23 1.517(4) . ? C17 C18 1.365(5) . ? C17 H17A 0.9300 . ? C18 C19 1.390(5) . ? C18 C21 1.506(5) . ? C19 C20 1.383(4) . ? C19 H19A 0.9300 . ? C20 C22 1.506(4) . ? C21 H21A 0.9600 . ? C21 H21B 0.9600 . ? C21 H21C 0.9600 . ? C22 H22A 0.9600 . ? C22 H22B 0.9600 . ? C22 H22C 0.9600 . ? C23 H23A 0.9600 . ? C23 H23B 0.9600 . ? C23 H23C 0.9600 . ? C24 C25 1.399(4) . ? C24 C29 1.408(4) . ? C25 C26 1.388(4) . ? C25 C32 1.516(5) . ? C26 C27 1.380(5) . ? C26 H26A 0.9300 . ? C27 C28 1.372(5) . ? C27 C31 1.512(5) . ? C28 C29 1.399(5) . ? C28 H28A 0.9300 . ? C29 C30 1.511(5) . ? C30 H30A 0.9600 . ? C30 H30B 0.9600 . ? C30 H30C 0.9600 . ? C31 H31A 0.9600 . ? C31 H31B 0.9600 . ? C31 H31C 0.9600 . ? C32 H32A 0.9600 . ? C32 H32B 0.9600 . ? C32 H32C 0.9600 . ? 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 C11 S1 C14 93.31(15) . . ? C3 N1 C2 121.0(3) . . ? C3 N1 C1 120.8(3) . . ? C2 N1 C1 118.3(3) . . ? C14 B1 C15 118.1(3) . . ? C14 B1 C24 115.5(3) . . ? C15 B1 C24 126.4(3) . . ? N1 C1 H1A 109.5 . . ? N1 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? N1 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? N1 C2 H2A 109.5 . . ? N1 C2 H2B 109.5 . . ? H2A C2 H2B 109.5 . . ? N1 C2 H2C 109.5 . . ? H2A C2 H2C 109.5 . . ? H2B C2 H2C 109.5 . . ? N1 C3 C8 121.7(3) . . ? N1 C3 C4 121.2(3) . . ? C8 C3 C4 117.0(3) . . ? C5 C4 C3 120.7(3) . . ? C5 C4 H4A 119.6 . . ? C3 C4 H4A 119.6 . . ? C4 C5 C6 122.1(3) . . ? C4 C5 H5A 119.0 . . ? C6 C5 H5A 119.0 . . ? C7 C6 C5 116.6(3) . . ? C7 C6 C9 120.3(3) . . ? C5 C6 C9 123.1(3) . . ? C8 C7 C6 122.0(3) . . ? C8 C7 H7A 119.0 . . ? C6 C7 H7A 119.0 . . ? C7 C8 C3 121.6(3) . . ? C7 C8 H8A 119.2 . . ? C3 C8 H8A 119.2 . . ? C10 C9 C6 128.5(3) . . ? C10 C9 H9A 115.8 . . ? C6 C9 H9A 115.8 . . ? C9 C10 C11 126.3(3) . . ? C9 C10 H10A 116.8 . . ? C11 C10 H10A 116.8 . . ? C12 C11 C10 126.5(3) . . ? C12 C11 S1 109.8(2) . . ? C10 C11 S1 123.7(3) . . ? C11 C12 C13 113.3(3) . . ? C11 C12 H12A 123.4 . . ? C13 C12 H12A 123.4 . . ? C14 C13 C12 114.7(3) . . ? C14 C13 H13A 122.6 . . ? C12 C13 H13A 122.6 . . ? C13 C14 B1 129.4(3) . . ? C13 C14 S1 108.8(2) . . ? B1 C14 S1 121.7(2) . . ? C20 C15 C16 117.5(3) . . ? C20 C15 B1 121.4(3) . . ? C16 C15 B1 121.0(3) . . ? C17 C16 C15 120.1(3) . . ? C17 C16 C23 117.7(3) . . ? C15 C16 C23 122.1(3) . . ? C18 C17 C16 123.0(3) . . ? C18 C17 H17A 118.5 . . ? C16 C17 H17A 118.5 . . ? C17 C18 C19 117.1(3) . . ? C17 C18 C21 121.5(4) . . ? C19 C18 C21 121.4(3) . . ? C20 C19 C18 122.2(3) . . ? C20 C19 H19A 118.9 . . ? C18 C19 H19A 118.9 . . ? C19 C20 C15 120.1(3) . . ? C19 C20 C22 118.5(3) . . ? C15 C20 C22 121.4(3) . . ? C18 C21 H21A 109.5 . . ? C18 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C18 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C20 C22 H22A 109.5 . . ? C20 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C20 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C16 C23 H23A 109.5 . . ? C16 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C16 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? C25 C24 C29 117.5(3) . . ? C25 C24 B1 121.2(3) . . ? C29 C24 B1 121.2(3) . . ? C26 C25 C24 120.7(3) . . ? C26 C25 C32 116.8(3) . . ? C24 C25 C32 122.5(3) . . ? C27 C26 C25 122.1(4) . . ? C27 C26 H26A 119.0 . . ? C25 C26 H26A 119.0 . . ? C28 C27 C26 117.4(3) . . ? C28 C27 C31 121.1(4) . . ? C26 C27 C31 121.5(4) . . ? C27 C28 C29 122.4(3) . . ? C27 C28 H28A 118.8 . . ? C29 C28 H28A 118.8 . . ? C28 C29 C24 119.8(3) . . ? C28 C29 C30 118.2(3) . . ? C24 C29 C30 121.9(3) . . ? C29 C30 H30A 109.5 . . ? C29 C30 H30B 109.5 . . ? H30A C30 H30B 109.5 . . ? C29 C30 H30C 109.5 . . ? H30A C30 H30C 109.5 . . ? H30B C30 H30C 109.5 . . ? C27 C31 H31A 109.5 . . ? C27 C31 H31B 109.5 . . ? H31A C31 H31B 109.5 . . ? C27 C31 H31C 109.5 . . ? H31A C31 H31C 109.5 . . ? H31B C31 H31C 109.5 . . ? C25 C32 H32A 109.5 . . ? C25 C32 H32B 109.5 . . ? H32A C32 H32B 109.5 . . ? C25 C32 H32C 109.5 . . ? H32A C32 H32C 109.5 . . ? H32B C32 H32C 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 C2 N1 C3 C8 11.4(6) . . . . ? C1 N1 C3 C8 -169.8(4) . . . . ? C2 N1 C3 C4 -169.9(4) . . . . ? C1 N1 C3 C4 8.9(5) . . . . ? N1 C3 C4 C5 -179.8(3) . . . . ? C8 C3 C4 C5 -1.0(5) . . . . ? C3 C4 C5 C6 2.2(5) . . . . ? C4 C5 C6 C7 -1.9(5) . . . . ? C4 C5 C6 C9 177.5(3) . . . . ? C5 C6 C7 C8 0.4(5) . . . . ? C9 C6 C7 C8 -179.0(3) . . . . ? C6 C7 C8 C3 0.8(6) . . . . ? N1 C3 C8 C7 178.3(3) . . . . ? C4 C3 C8 C7 -0.5(5) . . . . ? C7 C6 C9 C10 -177.1(4) . . . . ? C5 C6 C9 C10 3.6(6) . . . . ? C6 C9 C10 C11 -178.5(3) . . . . ? C9 C10 C11 C12 -174.2(3) . . . . ? C9 C10 C11 S1 6.2(5) . . . . ? C14 S1 C11 C12 1.7(3) . . . . ? C14 S1 C11 C10 -178.7(3) . . . . ? C10 C11 C12 C13 177.8(3) . . . . ? S1 C11 C12 C13 -2.6(4) . . . . ? C11 C12 C13 C14 2.5(4) . . . . ? C12 C13 C14 B1 173.9(3) . . . . ? C12 C13 C14 S1 -1.1(4) . . . . ? C15 B1 C14 C13 -155.0(3) . . . . ? C24 B1 C14 C13 23.1(5) . . . . ? C15 B1 C14 S1 19.4(4) . . . . ? C24 B1 C14 S1 -162.5(2) . . . . ? C11 S1 C14 C13 -0.3(3) . . . . ? C11 S1 C14 B1 -175.8(3) . . . . ? C14 B1 C15 C20 -120.0(3) . . . . ? C24 B1 C15 C20 62.2(4) . . . . ? C14 B1 C15 C16 56.8(4) . . . . ? C24 B1 C15 C16 -121.0(3) . . . . ? C20 C15 C16 C17 0.7(4) . . . . ? B1 C15 C16 C17 -176.2(3) . . . . ? C20 C15 C16 C23 -175.0(3) . . . . ? B1 C15 C16 C23 8.0(4) . . . . ? C15 C16 C17 C18 -0.9(5) . . . . ? C23 C16 C17 C18 175.0(3) . . . . ? C16 C17 C18 C19 -0.2(5) . . . . ? C16 C17 C18 C21 -179.9(3) . . . . ? C17 C18 C19 C20 1.4(5) . . . . ? C21 C18 C19 C20 -178.9(4) . . . . ? C18 C19 C20 C15 -1.6(5) . . . . ? C18 C19 C20 C22 176.7(3) . . . . ? C16 C15 C20 C19 0.5(4) . . . . ? B1 C15 C20 C19 177.4(3) . . . . ? C16 C15 C20 C22 -177.8(3) . . . . ? B1 C15 C20 C22 -0.8(4) . . . . ? C14 B1 C24 C25 56.0(4) . . . . ? C15 B1 C24 C25 -126.1(3) . . . . ? C14 B1 C24 C29 -120.0(3) . . . . ? C15 B1 C24 C29 57.9(4) . . . . ? C29 C24 C25 C26 2.3(5) . . . . ? B1 C24 C25 C26 -173.8(3) . . . . ? C29 C24 C25 C32 -175.9(3) . . . . ? B1 C24 C25 C32 7.9(5) . . . . ? C24 C25 C26 C27 0.0(5) . . . . ? C32 C25 C26 C27 178.3(3) . . . . ? C25 C26 C27 C28 -1.9(5) . . . . ? C25 C26 C27 C31 177.8(3) . . . . ? C26 C27 C28 C29 1.4(5) . . . . ? C31 C27 C28 C29 -178.3(3) . . . . ? C27 C28 C29 C24 0.9(5) . . . . ? C27 C28 C29 C30 178.3(3) . . . . ? C25 C24 C29 C28 -2.7(4) . . . . ? B1 C24 C29 C28 173.4(3) . . . . ? C25 C24 C29 C30 179.9(3) . . . . ? B1 C24 C29 C30 -3.9(5) . . . . ? _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 0.274 _refine_diff_density_min -0.225 _refine_diff_density_rms 0.043