# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2012 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_ha31 _database_code_depnum_ccdc_archive 'CCDC 888357' #TrackingRef 'HA31.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C30 H36 B N S Si' _chemical_formula_weight 481.56 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' B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Si Si 0.0817 0.0704 '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 Monoclinic _symmetry_space_group_name_H-M Pn loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x+1/2, -y, z+1/2' _cell_length_a 8.2220(3) _cell_length_b 9.0601(3) _cell_length_c 18.3261(7) _cell_angle_alpha 90.00 _cell_angle_beta 99.563(2) _cell_angle_gamma 90.00 _cell_volume 1346.18(8) _cell_formula_units_Z 2 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 1978 _cell_measurement_theta_min 2.51 _cell_measurement_theta_max 24.26 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.03 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.188 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 516 _exptl_absorpt_coefficient_mu 0.184 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9819 _exptl_absorpt_correction_T_max 0.9945 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 180(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 APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8934 _diffrn_reflns_av_R_equivalents 0.0484 _diffrn_reflns_av_sigmaI/netI 0.0930 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 2.25 _diffrn_reflns_theta_max 27.11 _reflns_number_total 5056 _reflns_number_gt 3526 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0430P)^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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.04(9) _refine_ls_number_reflns 5056 _refine_ls_number_parameters 316 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0937 _refine_ls_R_factor_gt 0.0534 _refine_ls_wR_factor_ref 0.1103 _refine_ls_wR_factor_gt 0.0954 _refine_ls_goodness_of_fit_ref 0.996 _refine_ls_restrained_S_all 0.996 _refine_ls_shift/su_max 0.002 _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 0.58521(10) 0.80241(11) 0.75531(5) 0.0351(3) Uani 1 1 d . . . Si1 Si 0.90426(11) 0.97575(12) 0.73590(6) 0.0320(3) Uani 1 1 d . . . N1 N 0.2643(3) 0.5852(3) 0.60909(15) 0.0272(7) Uani 1 1 d . . . B1 B 0.3986(5) 0.6321(5) 0.5538(2) 0.0259(9) Uani 1 1 d . . . C1 C 0.5134(4) 0.7334(4) 0.61575(19) 0.0258(8) Uani 1 1 d . . . C2 C 0.6635(4) 0.8170(4) 0.62635(19) 0.0289(8) Uani 1 1 d . . . H2A H 0.7218 0.8373 0.5868 0.035 Uiso 1 1 calc R . . C3 C 0.7182(4) 0.8663(4) 0.69756(19) 0.0306(9) Uani 1 1 d . . . C4 C 0.4619(4) 0.7164(4) 0.68287(18) 0.0275(8) Uani 1 1 d . . . C5 C 0.3130(4) 0.6342(4) 0.67950(19) 0.0273(8) Uani 1 1 d . . . C6 C 0.2161(5) 0.6069(4) 0.7340(2) 0.0336(9) Uani 1 1 d . . . H6A H 0.2536 0.6362 0.7838 0.040 Uiso 1 1 calc R . . C7 C 0.0665(5) 0.5377(4) 0.7152(2) 0.0385(10) Uani 1 1 d . . . H7A H 0.0006 0.5172 0.7520 0.046 Uiso 1 1 calc R . . C8 C 0.0126(5) 0.4980(4) 0.6426(2) 0.0391(10) Uani 1 1 d . . . H8A H -0.0931 0.4545 0.6281 0.047 Uiso 1 1 calc R . . C9 C 0.1144(5) 0.5223(4) 0.5913(2) 0.0332(9) Uani 1 1 d . . . H9A H 0.0777 0.4937 0.5414 0.040 Uiso 1 1 calc R . . C10 C 0.9882(5) 0.8999(5) 0.8286(2) 0.0461(11) Uani 1 1 d . . . H10A H 0.9084 0.9157 0.8621 0.069 Uiso 1 1 calc R . . H10B H 1.0918 0.9501 0.8483 0.069 Uiso 1 1 calc R . . H10C H 1.0086 0.7939 0.8244 0.069 Uiso 1 1 calc R . . C11 C 0.8539(5) 1.1725(4) 0.7480(2) 0.0421(10) Uani 1 1 d . . . H11A H 0.7750 1.1804 0.7824 0.063 Uiso 1 1 calc R . . H11B H 0.8052 1.2145 0.7000 0.063 Uiso 1 1 calc R . . H11C H 0.9547 1.2265 0.7679 0.063 Uiso 1 1 calc R . . C12 C 1.0493(5) 0.9623(5) 0.6677(2) 0.0445(11) Uani 1 1 d . . . H12A H 1.1569 1.0026 0.6897 0.067 Uiso 1 1 calc R . . H12B H 1.0050 1.0186 0.6231 0.067 Uiso 1 1 calc R . . H12C H 1.0619 0.8586 0.6545 0.067 Uiso 1 1 calc R . . C13 C 0.2776(4) 0.6947(4) 0.48066(18) 0.0263(8) Uani 1 1 d . . . C14 C 0.1960(4) 0.5944(4) 0.42667(19) 0.0289(8) Uani 1 1 d . . . C15 C 0.0712(4) 0.6427(4) 0.37074(18) 0.0312(9) Uani 1 1 d . . . H15A H 0.0175 0.5729 0.3362 0.037 Uiso 1 1 calc R . . C16 C 0.0232(4) 0.7898(5) 0.36407(19) 0.0312(9) Uani 1 1 d . . . C17 C 0.1091(4) 0.8880(5) 0.41312(19) 0.0332(9) Uani 1 1 d . . . H17A H 0.0828 0.9899 0.4076 0.040 Uiso 1 1 calc R . . C18 C 0.2333(4) 0.8451(4) 0.47081(18) 0.0275(8) Uani 1 1 d . . . C19 C 0.3159(5) 0.9660(4) 0.5204(2) 0.0359(9) Uani 1 1 d . . . H19A H 0.2670 1.0614 0.5039 0.054 Uiso 1 1 calc R . . H19B H 0.4341 0.9675 0.5180 0.054 Uiso 1 1 calc R . . H19C H 0.3002 0.9475 0.5715 0.054 Uiso 1 1 calc R . . C20 C -0.1163(5) 0.8395(5) 0.3050(2) 0.0445(11) Uani 1 1 d . . . H20A H -0.1900 0.9048 0.3270 0.067 Uiso 1 1 calc R . . H20B H -0.1781 0.7532 0.2834 0.067 Uiso 1 1 calc R . . H20C H -0.0713 0.8929 0.2663 0.067 Uiso 1 1 calc R . . C21 C 0.2348(5) 0.4295(4) 0.4254(2) 0.0394(10) Uani 1 1 d . . . H21A H 0.1441 0.3781 0.3940 0.059 Uiso 1 1 calc R . . H21B H 0.2479 0.3900 0.4758 0.059 Uiso 1 1 calc R . . H21C H 0.3371 0.4147 0.4055 0.059 Uiso 1 1 calc R . . C22 C 0.5251(4) 0.4999(4) 0.53656(18) 0.0259(8) Uani 1 1 d . . . C23 C 0.5470(4) 0.3584(4) 0.56813(19) 0.0280(8) Uani 1 1 d . . . C24 C 0.6561(4) 0.2573(4) 0.5462(2) 0.0322(9) Uani 1 1 d . . . H24A H 0.6648 0.1619 0.5681 0.039 Uiso 1 1 calc R . . C25 C 0.7531(4) 0.2915(5) 0.49309(19) 0.0320(9) Uani 1 1 d . . . C26 C 0.7389(4) 0.4327(4) 0.46414(19) 0.0324(9) Uani 1 1 d . . . H26A H 0.8062 0.4602 0.4290 0.039 Uiso 1 1 calc R . . C27 C 0.6293(4) 0.5360(4) 0.48469(19) 0.0283(9) Uani 1 1 d . . . C28 C 0.6254(5) 0.6850(4) 0.4458(2) 0.0388(10) Uani 1 1 d . . . H28A H 0.7370 0.7111 0.4381 0.058 Uiso 1 1 calc R . . H28B H 0.5845 0.7606 0.4765 0.058 Uiso 1 1 calc R . . H28C H 0.5523 0.6792 0.3979 0.058 Uiso 1 1 calc R . . C29 C 0.8712(5) 0.1805(5) 0.4707(2) 0.0445(11) Uani 1 1 d . . . H29A H 0.8832 0.1973 0.4191 0.067 Uiso 1 1 calc R . . H29B H 0.8287 0.0807 0.4760 0.067 Uiso 1 1 calc R . . H29C H 0.9789 0.1912 0.5025 0.067 Uiso 1 1 calc R . . C30 C 0.4525(5) 0.3058(4) 0.6277(2) 0.0367(10) Uani 1 1 d . . . H30A H 0.4901 0.2066 0.6439 0.055 Uiso 1 1 calc R . . H30B H 0.3343 0.3030 0.6077 0.055 Uiso 1 1 calc R . . H30C H 0.4720 0.3737 0.6699 0.055 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 0.0332(5) 0.0486(6) 0.0235(5) -0.0024(5) 0.0049(4) -0.0084(5) Si1 0.0258(5) 0.0432(7) 0.0265(5) -0.0013(5) 0.0027(4) -0.0056(5) N1 0.0215(16) 0.0351(18) 0.0251(16) -0.0024(14) 0.0037(12) -0.0024(14) B1 0.022(2) 0.030(2) 0.026(2) 0.0014(19) 0.0062(17) -0.0013(19) C1 0.0245(19) 0.029(2) 0.0252(19) 0.0004(16) 0.0077(15) 0.0024(16) C2 0.027(2) 0.034(2) 0.0256(19) 0.0029(17) 0.0029(16) -0.0013(17) C3 0.025(2) 0.037(2) 0.029(2) 0.0031(17) 0.0024(16) -0.0027(18) C4 0.026(2) 0.031(2) 0.0254(19) -0.0022(16) 0.0026(15) -0.0040(17) C5 0.0248(19) 0.029(2) 0.028(2) -0.0012(16) 0.0050(15) 0.0033(17) C6 0.034(2) 0.041(2) 0.028(2) -0.0032(18) 0.0110(17) -0.0020(19) C7 0.034(2) 0.045(3) 0.039(2) -0.001(2) 0.0157(18) -0.005(2) C8 0.025(2) 0.050(3) 0.043(2) -0.001(2) 0.0086(18) -0.009(2) C9 0.032(2) 0.036(2) 0.031(2) -0.0054(18) 0.0076(17) -0.0021(19) C10 0.035(2) 0.061(3) 0.040(2) 0.003(2) 0.0008(19) -0.003(2) C11 0.045(3) 0.048(3) 0.034(2) -0.004(2) 0.0098(18) -0.012(2) C12 0.034(2) 0.065(3) 0.036(2) -0.002(2) 0.0104(19) -0.006(2) C13 0.023(2) 0.032(2) 0.0249(19) -0.0036(16) 0.0089(15) -0.0038(17) C14 0.025(2) 0.038(2) 0.0248(19) -0.0013(17) 0.0079(15) -0.0033(18) C15 0.027(2) 0.047(3) 0.0208(19) -0.0052(17) 0.0058(15) -0.0049(19) C16 0.023(2) 0.048(3) 0.0238(19) 0.0035(17) 0.0075(16) 0.0008(19) C17 0.029(2) 0.043(3) 0.031(2) 0.0031(18) 0.0149(17) 0.0080(19) C18 0.0212(18) 0.036(2) 0.0272(19) -0.0023(17) 0.0097(15) 0.0006(17) C19 0.037(2) 0.036(2) 0.035(2) -0.0053(18) 0.0045(17) 0.0023(19) C20 0.038(2) 0.065(3) 0.030(2) 0.002(2) 0.0042(18) 0.009(2) C21 0.037(2) 0.039(3) 0.040(2) -0.0117(19) -0.0006(19) -0.004(2) C22 0.0206(18) 0.033(2) 0.0227(17) -0.0051(16) -0.0005(14) -0.0047(16) C23 0.0243(19) 0.031(2) 0.0293(19) 0.0001(17) 0.0076(15) -0.0002(17) C24 0.029(2) 0.034(2) 0.033(2) 0.0003(18) 0.0027(17) 0.0023(18) C25 0.022(2) 0.042(3) 0.031(2) -0.0097(18) 0.0016(16) 0.0028(18) C26 0.027(2) 0.048(3) 0.0239(19) -0.0032(18) 0.0086(16) 0.0031(19) C27 0.027(2) 0.034(2) 0.0248(18) 0.0009(17) 0.0053(15) 0.0007(18) C28 0.036(2) 0.046(3) 0.037(2) 0.0052(19) 0.0121(18) 0.005(2) C29 0.035(2) 0.051(3) 0.048(3) -0.008(2) 0.0076(19) 0.008(2) C30 0.041(2) 0.032(2) 0.040(2) 0.0053(18) 0.0173(18) 0.002(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 C4 1.718(3) . ? S1 C3 1.743(4) . ? Si1 C11 1.851(4) . ? Si1 C10 1.856(4) . ? Si1 C3 1.860(4) . ? Si1 C12 1.869(4) . ? N1 C9 1.347(4) . ? N1 C5 1.360(4) . ? N1 B1 1.673(5) . ? B1 C13 1.632(5) . ? B1 C1 1.633(5) . ? B1 C22 1.651(5) . ? C1 C4 1.375(4) . ? C1 C2 1.434(5) . ? C2 C3 1.382(5) . ? C2 H2A 0.9500 . ? C4 C5 1.425(5) . ? C5 C6 1.400(5) . ? C6 C7 1.373(5) . ? C6 H6A 0.9500 . ? C7 C8 1.380(5) . ? C7 H7A 0.9500 . ? C8 C9 1.377(5) . ? C8 H8A 0.9500 . ? C9 H9A 0.9500 . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? C13 C18 1.414(5) . ? C13 C14 1.426(5) . ? C14 C15 1.395(5) . ? C14 C21 1.529(5) . ? C15 C16 1.390(5) . ? C15 H15A 0.9500 . ? C16 C17 1.374(5) . ? C16 C20 1.509(5) . ? C17 C18 1.398(5) . ? C17 H17A 0.9500 . ? C18 C19 1.510(5) . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C20 H20C 0.9800 . ? C21 H21A 0.9800 . ? C21 H21B 0.9800 . ? C21 H21C 0.9800 . ? C22 C23 1.405(5) . ? C22 C27 1.420(5) . ? C23 C24 1.387(5) . ? C23 C30 1.518(5) . ? C24 C25 1.392(5) . ? C24 H24A 0.9500 . ? C25 C26 1.382(5) . ? C25 C29 1.501(5) . ? C26 C27 1.394(5) . ? C26 H26A 0.9500 . ? C27 C28 1.524(5) . ? C28 H28A 0.9800 . ? C28 H28B 0.9800 . ? C28 H28C 0.9800 . ? C29 H29A 0.9800 . ? C29 H29B 0.9800 . ? C29 H29C 0.9800 . ? C30 H30A 0.9800 . ? C30 H30B 0.9800 . ? C30 H30C 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 C4 S1 C3 91.77(17) . . ? C11 Si1 C10 107.66(19) . . ? C11 Si1 C3 111.84(18) . . ? C10 Si1 C3 107.80(17) . . ? C11 Si1 C12 108.9(2) . . ? C10 Si1 C12 113.99(19) . . ? C3 Si1 C12 106.76(17) . . ? C9 N1 C5 118.8(3) . . ? C9 N1 B1 129.0(3) . . ? C5 N1 B1 111.8(3) . . ? C13 B1 C1 125.4(3) . . ? C13 B1 C22 114.3(3) . . ? C1 B1 C22 103.4(3) . . ? C13 B1 N1 102.2(3) . . ? C1 B1 N1 94.9(3) . . ? C22 B1 N1 115.6(3) . . ? C4 C1 C2 108.9(3) . . ? C4 C1 B1 109.3(3) . . ? C2 C1 B1 140.9(3) . . ? C3 C2 C1 115.9(3) . . ? C3 C2 H2A 122.1 . . ? C1 C2 H2A 122.1 . . ? C2 C3 S1 109.1(3) . . ? C2 C3 Si1 130.3(3) . . ? S1 C3 Si1 120.5(2) . . ? C1 C4 C5 114.2(3) . . ? C1 C4 S1 114.2(3) . . ? C5 C4 S1 131.5(3) . . ? N1 C5 C6 120.5(3) . . ? N1 C5 C4 109.1(3) . . ? C6 C5 C4 130.4(3) . . ? C7 C6 C5 119.6(3) . . ? C7 C6 H6A 120.2 . . ? C5 C6 H6A 120.2 . . ? C6 C7 C8 119.5(4) . . ? C6 C7 H7A 120.3 . . ? C8 C7 H7A 120.3 . . ? C9 C8 C7 118.9(4) . . ? C9 C8 H8A 120.6 . . ? C7 C8 H8A 120.6 . . ? N1 C9 C8 122.6(3) . . ? N1 C9 H9A 118.7 . . ? C8 C9 H9A 118.7 . . ? Si1 C10 H10A 109.5 . . ? Si1 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? Si1 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? Si1 C11 H11A 109.5 . . ? Si1 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? Si1 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? Si1 C12 H12A 109.5 . . ? Si1 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? Si1 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C18 C13 C14 116.3(3) . . ? C18 C13 B1 123.3(3) . . ? C14 C13 B1 120.0(3) . . ? C15 C14 C13 120.9(3) . . ? C15 C14 C21 115.1(3) . . ? C13 C14 C21 123.9(3) . . ? C16 C15 C14 121.9(3) . . ? C16 C15 H15A 119.0 . . ? C14 C15 H15A 119.0 . . ? C17 C16 C15 117.1(3) . . ? C17 C16 C20 121.5(4) . . ? C15 C16 C20 121.4(3) . . ? C16 C17 C18 123.1(4) . . ? C16 C17 H17A 118.4 . . ? C18 C17 H17A 118.4 . . ? C17 C18 C13 120.3(3) . . ? C17 C18 C19 116.9(3) . . ? C13 C18 C19 122.8(3) . . ? C18 C19 H19A 109.5 . . ? C18 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C18 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C16 C20 H20A 109.5 . . ? C16 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C16 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C14 C21 H21A 109.5 . . ? C14 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C14 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C23 C22 C27 115.8(3) . . ? C23 C22 B1 128.7(3) . . ? C27 C22 B1 115.5(3) . . ? C24 C23 C22 121.9(3) . . ? C24 C23 C30 115.7(3) . . ? C22 C23 C30 122.4(3) . . ? C23 C24 C25 121.9(4) . . ? C23 C24 H24A 119.0 . . ? C25 C24 H24A 119.0 . . ? C26 C25 C24 116.9(3) . . ? C26 C25 C29 122.1(4) . . ? C24 C25 C29 120.9(4) . . ? C25 C26 C27 122.3(3) . . ? C25 C26 H26A 118.8 . . ? C27 C26 H26A 118.8 . . ? C26 C27 C22 121.0(3) . . ? C26 C27 C28 115.7(3) . . ? C22 C27 C28 123.3(3) . . ? C27 C28 H28A 109.5 . . ? C27 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? C27 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? C25 C29 H29A 109.5 . . ? C25 C29 H29B 109.5 . . ? H29A C29 H29B 109.5 . . ? C25 C29 H29C 109.5 . . ? H29A C29 H29C 109.5 . . ? H29B C29 H29C 109.5 . . ? C23 C30 H30A 109.5 . . ? C23 C30 H30B 109.5 . . ? H30A C30 H30B 109.5 . . ? C23 C30 H30C 109.5 . . ? H30A C30 H30C 109.5 . . ? H30B C30 H30C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 27.11 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.340 _refine_diff_density_min -0.380 _refine_diff_density_rms 0.058 data_louis49 _database_code_depnum_ccdc_archive 'CCDC 888358' #TrackingRef 'LOUIS49.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C36 H33 B Cl2 N S' _chemical_formula_weight 593.40 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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 '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 13.9623(15) _cell_length_b 26.777(3) _cell_length_c 8.7487(8) _cell_angle_alpha 90.00 _cell_angle_beta 108.141(2) _cell_angle_gamma 90.00 _cell_volume 3108.3(5) _cell_formula_units_Z 4 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 4616 _cell_measurement_theta_min 2.16 _cell_measurement_theta_max 22.02 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.268 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1244 _exptl_absorpt_coefficient_mu 0.302 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9704 _exptl_absorpt_correction_T_max 0.9850 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 180(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 APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 42368 _diffrn_reflns_av_R_equivalents 0.0795 _diffrn_reflns_av_sigmaI/netI 0.0516 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -33 _diffrn_reflns_limit_k_max 33 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 1.52 _diffrn_reflns_theta_max 26.00 _reflns_number_total 6119 _reflns_number_gt 3743 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0500P)^2^+2.0000P] 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 6119 _refine_ls_number_parameters 376 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1098 _refine_ls_R_factor_gt 0.0566 _refine_ls_wR_factor_ref 0.1443 _refine_ls_wR_factor_gt 0.1190 _refine_ls_goodness_of_fit_ref 1.056 _refine_ls_restrained_S_all 1.056 _refine_ls_shift/su_max 0.001 _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 0.92996(6) 0.02661(4) 0.25525(13) 0.0670(3) Uani 1 1 d . . . N1 N 0.71163(16) 0.06512(8) -0.5471(3) 0.0342(5) Uani 1 1 d . . . B1 B 0.6788(2) 0.12253(11) -0.6213(4) 0.0301(7) Uani 1 1 d . . . Cl1 Cl 1.69479(8) -0.13891(4) 2.11915(12) 0.0808(3) Uani 1 1 d . . . Cl2 Cl 1.79305(9) -0.15448(4) 1.87537(14) 0.0870(4) Uani 1 1 d . . . C1 C 0.6389(2) 0.10463(11) -0.8071(3) 0.0370(7) Uani 1 1 d . . . C2 C 0.5887(2) 0.13070(14) -0.9463(4) 0.0501(8) Uani 1 1 d . . . H2A H 0.5746 0.1652 -0.9404 0.060 Uiso 1 1 calc R . . C3 C 0.5590(3) 0.10639(19) -1.0941(4) 0.0723(12) Uani 1 1 d . . . H3A H 0.5264 0.1248 -1.1889 0.087 Uiso 1 1 calc R . . C4 C 0.5761(3) 0.0558(2) -1.1054(5) 0.0877(16) Uani 1 1 d . . . H4A H 0.5559 0.0399 -1.2075 0.105 Uiso 1 1 calc R . . C5 C 0.6218(3) 0.02876(16) -0.9705(5) 0.0721(12) Uani 1 1 d . . . H5A H 0.6325 -0.0061 -0.9772 0.086 Uiso 1 1 calc R . . C6 C 0.6528(2) 0.05334(12) -0.8217(4) 0.0451(8) Uani 1 1 d . . . C7 C 0.6987(2) 0.03059(11) -0.6661(4) 0.0436(8) Uani 1 1 d . . . C8 C 0.7280(3) -0.01874(12) -0.6278(5) 0.0587(10) Uani 1 1 d . . . H8A H 0.7184 -0.0429 -0.7109 0.070 Uiso 1 1 calc R . . C9 C 0.7706(3) -0.03255(12) -0.4705(6) 0.0636(11) Uani 1 1 d . . . H9A H 0.7911 -0.0661 -0.4442 0.076 Uiso 1 1 calc R . . C10 C 0.7837(2) 0.00296(12) -0.3492(5) 0.0509(9) Uani 1 1 d . . . C11 C 0.7538(2) 0.05159(11) -0.3944(4) 0.0411(7) Uani 1 1 d . . . H11A H 0.7638 0.0763 -0.3130 0.049 Uiso 1 1 calc R . . C12 C 0.8275(2) -0.00823(13) -0.1818(5) 0.0645(11) Uani 1 1 d . . . C13 C 0.8663(2) -0.01662(13) -0.0426(6) 0.0670(12) Uani 1 1 d . . . C14 C 0.9113(2) -0.02394(13) 0.1256(5) 0.0655(11) Uani 1 1 d . . . C15 C 0.9472(3) -0.06713(14) 0.2083(5) 0.0731(13) Uani 1 1 d . . . H15A H 0.9447 -0.0988 0.1585 0.088 Uiso 1 1 calc R . . C16 C 0.9879(2) -0.05930(14) 0.3739(5) 0.0702(12) Uani 1 1 d . . . H16A H 1.0161 -0.0855 0.4475 0.084 Uiso 1 1 calc R . . C17 C 0.9837(2) -0.01093(13) 0.4211(4) 0.0617(11) Uani 1 1 d . . . C18 C 0.78624(19) 0.15307(9) -0.5490(3) 0.0274(6) Uani 1 1 d . . . C19 C 0.8534(2) 0.16265(9) -0.6392(3) 0.0320(6) Uani 1 1 d . . . C20 C 0.9465(2) 0.18548(10) -0.5672(4) 0.0383(7) Uani 1 1 d . . . H20A H 0.9898 0.1909 -0.6304 0.046 Uiso 1 1 calc R . . C21 C 0.9783(2) 0.20049(11) -0.4088(4) 0.0406(7) Uani 1 1 d . . . C22 C 0.9132(2) 0.19226(10) -0.3212(4) 0.0384(7) Uani 1 1 d . . . H22A H 0.9329 0.2025 -0.2118 0.046 Uiso 1 1 calc R . . C23 C 0.8190(2) 0.16945(10) -0.3872(3) 0.0318(6) Uani 1 1 d . . . C24 C 0.7570(2) 0.16703(12) -0.2731(3) 0.0418(7) Uani 1 1 d . . . H24A H 0.7965 0.1509 -0.1727 0.063 Uiso 1 1 calc R . . H24B H 0.6956 0.1477 -0.3226 0.063 Uiso 1 1 calc R . . H24C H 0.7389 0.2009 -0.2502 0.063 Uiso 1 1 calc R . . C25 C 1.0787(2) 0.22569(15) -0.3349(5) 0.0665(11) Uani 1 1 d . . . H25A H 1.1312 0.2072 -0.3637 0.100 Uiso 1 1 calc R . . H25B H 1.0947 0.2262 -0.2176 0.100 Uiso 1 1 calc R . . H25C H 1.0756 0.2600 -0.3752 0.100 Uiso 1 1 calc R . . C26 C 0.8290(2) 0.15220(11) -0.8175(3) 0.0427(7) Uani 1 1 d . . . H26A H 0.8893 0.1576 -0.8500 0.064 Uiso 1 1 calc R . . H26B H 0.7753 0.1747 -0.8783 0.064 Uiso 1 1 calc R . . H26C H 0.8065 0.1175 -0.8396 0.064 Uiso 1 1 calc R . . C27 C 0.58017(19) 0.14603(9) -0.5817(3) 0.0275(6) Uani 1 1 d . . . C28 C 0.5627(2) 0.19832(10) -0.5947(3) 0.0318(6) Uani 1 1 d . . . C29 C 0.4802(2) 0.21971(10) -0.5629(3) 0.0362(7) Uani 1 1 d . . . H29A H 0.4714 0.2549 -0.5729 0.043 Uiso 1 1 calc R . . C30 C 0.4105(2) 0.19166(10) -0.5173(3) 0.0370(7) Uani 1 1 d . . . C31 C 0.4231(2) 0.14038(10) -0.5138(3) 0.0350(7) Uani 1 1 d . . . H31A H 0.3752 0.1200 -0.4863 0.042 Uiso 1 1 calc R . . C32 C 0.5038(2) 0.11737(10) -0.5491(3) 0.0315(6) Uani 1 1 d . . . C33 C 0.6314(2) 0.23419(10) -0.6449(4) 0.0424(8) Uani 1 1 d . . . H33A H 0.5936 0.2643 -0.6911 0.064 Uiso 1 1 calc R . . H33B H 0.6568 0.2182 -0.7253 0.064 Uiso 1 1 calc R . . H33C H 0.6882 0.2433 -0.5507 0.064 Uiso 1 1 calc R . . C34 C 0.3228(2) 0.21575(13) -0.4783(4) 0.0520(9) Uani 1 1 d . . . H34A H 0.2956 0.2430 -0.5543 0.078 Uiso 1 1 calc R . . H34B H 0.3460 0.2291 -0.3686 0.078 Uiso 1 1 calc R . . H34C H 0.2702 0.1908 -0.4866 0.078 Uiso 1 1 calc R . . C35 C 0.5001(2) 0.06098(10) -0.5584(4) 0.0421(7) Uani 1 1 d . . . H35A H 0.4353 0.0492 -0.5505 0.063 Uiso 1 1 calc R . . H35B H 0.5550 0.0470 -0.4697 0.063 Uiso 1 1 calc R . . H35C H 0.5075 0.0501 -0.6611 0.063 Uiso 1 1 calc R . . C36 C 1.6873(3) -0.13126(16) 1.9179(5) 0.0788(13) Uani 1 1 d . . . H36A H 1.6799 -0.0953 1.8907 0.095 Uiso 1 1 calc R . . H36B H 1.6264 -0.1486 1.8494 0.095 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 0.0392(5) 0.0604(6) 0.1038(8) 0.0508(6) 0.0256(5) 0.0168(4) N1 0.0317(12) 0.0286(12) 0.0453(15) -0.0001(11) 0.0166(11) 0.0013(10) B1 0.0345(17) 0.0254(16) 0.0300(16) 0.0035(13) 0.0096(14) -0.0001(13) Cl1 0.0849(7) 0.0879(8) 0.0604(6) -0.0147(5) 0.0092(5) 0.0110(6) Cl2 0.0788(7) 0.0998(9) 0.0762(7) -0.0141(6) 0.0149(6) 0.0122(6) C1 0.0338(15) 0.0464(18) 0.0342(16) -0.0050(13) 0.0153(13) -0.0070(13) C2 0.0416(18) 0.073(2) 0.0340(17) -0.0032(16) 0.0098(14) -0.0078(17) C3 0.055(2) 0.129(4) 0.0322(19) -0.007(2) 0.0128(17) -0.026(2) C4 0.093(3) 0.134(4) 0.046(3) -0.046(3) 0.037(2) -0.056(3) C5 0.089(3) 0.074(3) 0.074(3) -0.045(2) 0.055(2) -0.040(2) C6 0.0469(18) 0.0482(19) 0.050(2) -0.0178(16) 0.0299(16) -0.0160(15) C7 0.0424(17) 0.0315(16) 0.069(2) -0.0106(15) 0.0351(17) -0.0063(14) C8 0.064(2) 0.0328(18) 0.101(3) -0.0090(19) 0.056(2) -0.0085(16) C9 0.053(2) 0.0275(18) 0.130(4) 0.014(2) 0.056(2) 0.0053(15) C10 0.0320(17) 0.0388(18) 0.086(3) 0.0233(18) 0.0246(17) 0.0057(14) C11 0.0344(16) 0.0356(17) 0.052(2) 0.0079(14) 0.0122(14) 0.0021(13) C12 0.0372(19) 0.049(2) 0.109(3) 0.044(2) 0.024(2) 0.0084(16) C13 0.0348(18) 0.056(2) 0.108(3) 0.045(2) 0.019(2) 0.0086(16) C14 0.0330(18) 0.057(2) 0.102(3) 0.041(2) 0.0137(19) 0.0039(16) C15 0.040(2) 0.058(2) 0.108(3) 0.038(2) 0.003(2) 0.0011(17) C16 0.0335(18) 0.052(2) 0.109(3) 0.043(2) 0.000(2) 0.0030(16) C17 0.0224(17) 0.058(2) 0.100(3) 0.044(2) 0.0112(18) 0.0049(15) C18 0.0298(14) 0.0224(13) 0.0313(15) 0.0035(11) 0.0113(12) 0.0058(11) C19 0.0360(15) 0.0277(14) 0.0351(16) 0.0057(12) 0.0153(13) 0.0034(12) C20 0.0358(16) 0.0341(16) 0.0502(19) 0.0062(14) 0.0207(14) 0.0016(13) C21 0.0315(16) 0.0346(16) 0.0528(19) 0.0019(14) 0.0090(14) -0.0006(13) C22 0.0378(17) 0.0356(16) 0.0371(16) -0.0038(13) 0.0051(13) -0.0001(13) C23 0.0344(15) 0.0277(14) 0.0327(15) 0.0007(12) 0.0097(12) 0.0034(12) C24 0.0446(17) 0.0510(19) 0.0316(16) -0.0066(14) 0.0143(14) -0.0010(15) C25 0.0394(19) 0.077(3) 0.079(3) -0.007(2) 0.0126(18) -0.0163(18) C26 0.0485(18) 0.0487(18) 0.0369(17) 0.0058(14) 0.0219(14) -0.0004(15) C27 0.0302(14) 0.0285(14) 0.0221(13) 0.0015(11) 0.0055(11) 0.0006(11) C28 0.0320(15) 0.0308(15) 0.0307(15) 0.0025(12) 0.0072(12) 0.0009(12) C29 0.0390(16) 0.0280(15) 0.0375(16) 0.0008(12) 0.0062(13) 0.0052(13) C30 0.0339(16) 0.0397(17) 0.0341(16) -0.0011(13) 0.0060(13) 0.0059(13) C31 0.0310(15) 0.0382(16) 0.0349(16) 0.0046(13) 0.0089(12) -0.0014(13) C32 0.0343(15) 0.0311(15) 0.0279(14) 0.0034(11) 0.0081(12) 0.0016(12) C33 0.0441(18) 0.0279(15) 0.055(2) 0.0080(14) 0.0146(15) 0.0024(13) C34 0.0458(19) 0.059(2) 0.054(2) -0.0044(17) 0.0203(16) 0.0131(16) C35 0.0376(16) 0.0314(16) 0.060(2) 0.0023(14) 0.0190(15) -0.0062(13) C36 0.082(3) 0.083(3) 0.061(3) 0.000(2) 0.007(2) 0.034(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 C17 1.732(3) . ? S1 C14 1.733(4) . ? N1 C11 1.331(4) . ? N1 C7 1.362(4) . ? N1 B1 1.676(4) . ? B1 C1 1.619(4) . ? B1 C27 1.646(4) . ? B1 C18 1.652(4) . ? Cl1 C36 1.743(4) . ? Cl2 C36 1.746(4) . ? C1 C2 1.389(4) . ? C1 C6 1.398(4) . ? C2 C3 1.391(5) . ? C2 H2A 0.9500 . ? C3 C4 1.383(6) . ? C3 H3A 0.9500 . ? C4 C5 1.363(6) . ? C4 H4A 0.9500 . ? C5 C6 1.402(4) . ? C5 H5A 0.9500 . ? C6 C7 1.446(4) . ? C7 C8 1.392(4) . ? C8 C9 1.369(5) . ? C8 H8A 0.9500 . ? C9 C10 1.394(5) . ? C9 H9A 0.9500 . ? C10 C11 1.387(4) . ? C10 C12 1.432(5) . ? C11 H11A 0.9500 . ? C12 C13 1.190(5) . ? C13 C14 1.422(6) . ? C14 C15 1.373(4) . ? C15 C16 1.397(6) . ? C15 H15A 0.9500 . ? C16 C17 1.366(5) . ? C16 H16A 0.9500 . ? C17 C17 1.437(8) 3_756 ? C18 C23 1.415(4) . ? C18 C19 1.424(4) . ? C19 C20 1.396(4) . ? C19 C26 1.516(4) . ? C20 C21 1.376(4) . ? C20 H20A 0.9500 . ? C21 C22 1.377(4) . ? C21 C25 1.508(4) . ? C22 C23 1.401(4) . ? C22 H22A 0.9500 . ? C23 C24 1.512(4) . ? C24 H24A 0.9800 . ? C24 H24B 0.9800 . ? C24 H24C 0.9800 . ? C25 H25A 0.9800 . ? C25 H25B 0.9800 . ? C25 H25C 0.9800 . ? C26 H26A 0.9800 . ? C26 H26B 0.9800 . ? C26 H26C 0.9800 . ? C27 C32 1.413(4) . ? C27 C28 1.419(4) . ? C28 C29 1.390(4) . ? C28 C33 1.515(4) . ? C29 C30 1.383(4) . ? C29 H29A 0.9500 . ? C30 C31 1.384(4) . ? C30 C34 1.514(4) . ? C31 C32 1.400(4) . ? C31 H31A 0.9500 . ? C32 C35 1.512(4) . ? C33 H33A 0.9800 . ? C33 H33B 0.9800 . ? C33 H33C 0.9800 . ? C34 H34A 0.9800 . ? C34 H34B 0.9800 . ? C34 H34C 0.9800 . ? C35 H35A 0.9800 . ? C35 H35B 0.9800 . ? C35 H35C 0.9800 . ? C36 H36A 0.9900 . ? C36 H36B 0.9900 . ? 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 C17 S1 C14 91.86(18) . . ? C11 N1 C7 119.6(3) . . ? C11 N1 B1 128.3(2) . . ? C7 N1 B1 111.8(2) . . ? C1 B1 C27 106.0(2) . . ? C1 B1 C18 121.2(2) . . ? C27 B1 C18 116.7(2) . . ? C1 B1 N1 94.8(2) . . ? C27 B1 N1 114.5(2) . . ? C18 B1 N1 101.5(2) . . ? C2 C1 C6 117.4(3) . . ? C2 C1 B1 130.8(3) . . ? C6 C1 B1 111.6(3) . . ? C1 C2 C3 120.2(4) . . ? C1 C2 H2A 119.9 . . ? C3 C2 H2A 119.9 . . ? C4 C3 C2 121.1(4) . . ? C4 C3 H3A 119.5 . . ? C2 C3 H3A 119.5 . . ? C5 C4 C3 120.2(4) . . ? C5 C4 H4A 119.9 . . ? C3 C4 H4A 119.9 . . ? C4 C5 C6 118.7(4) . . ? C4 C5 H5A 120.6 . . ? C6 C5 H5A 120.6 . . ? C1 C6 C5 122.3(3) . . ? C1 C6 C7 111.2(3) . . ? C5 C6 C7 126.5(3) . . ? N1 C7 C8 120.1(3) . . ? N1 C7 C6 110.3(3) . . ? C8 C7 C6 129.6(3) . . ? C9 C8 C7 120.1(3) . . ? C9 C8 H8A 120.0 . . ? C7 C8 H8A 120.0 . . ? C8 C9 C10 119.6(3) . . ? C8 C9 H9A 120.2 . . ? C10 C9 H9A 120.2 . . ? C11 C10 C9 117.8(3) . . ? C11 C10 C12 118.9(3) . . ? C9 C10 C12 123.3(3) . . ? N1 C11 C10 122.8(3) . . ? N1 C11 H11A 118.6 . . ? C10 C11 H11A 118.6 . . ? C13 C12 C10 178.0(4) . . ? C12 C13 C14 176.9(4) . . ? C15 C14 C13 129.2(4) . . ? C15 C14 S1 110.9(3) . . ? C13 C14 S1 119.8(3) . . ? C14 C15 C16 112.6(4) . . ? C14 C15 H15A 123.7 . . ? C16 C15 H15A 123.7 . . ? C17 C16 C15 114.5(3) . . ? C17 C16 H16A 122.8 . . ? C15 C16 H16A 122.8 . . ? C16 C17 C17 130.2(4) . 3_756 ? C16 C17 S1 110.2(3) . . ? C17 C17 S1 119.6(4) 3_756 . ? C23 C18 C19 115.8(2) . . ? C23 C18 B1 120.6(2) . . ? C19 C18 B1 123.6(2) . . ? C20 C19 C18 120.7(3) . . ? C20 C19 C26 115.1(2) . . ? C18 C19 C26 124.1(2) . . ? C21 C20 C19 123.1(3) . . ? C21 C20 H20A 118.5 . . ? C19 C20 H20A 118.5 . . ? C20 C21 C22 116.8(3) . . ? C20 C21 C25 121.9(3) . . ? C22 C21 C25 121.3(3) . . ? C21 C22 C23 122.6(3) . . ? C21 C22 H22A 118.7 . . ? C23 C22 H22A 118.7 . . ? C22 C23 C18 121.1(3) . . ? C22 C23 C24 113.8(2) . . ? C18 C23 C24 125.0(2) . . ? C23 C24 H24A 109.5 . . ? C23 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C23 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? C21 C25 H25A 109.5 . . ? C21 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? C21 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? C19 C26 H26A 109.5 . . ? C19 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? C19 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? C32 C27 C28 115.5(2) . . ? C32 C27 B1 124.6(2) . . ? C28 C27 B1 119.6(2) . . ? C29 C28 C27 121.5(2) . . ? C29 C28 C33 115.8(2) . . ? C27 C28 C33 122.7(2) . . ? C30 C29 C28 122.4(3) . . ? C30 C29 H29A 118.8 . . ? C28 C29 H29A 118.8 . . ? C29 C30 C31 116.7(3) . . ? C29 C30 C34 121.7(3) . . ? C31 C30 C34 121.6(3) . . ? C30 C31 C32 122.5(3) . . ? C30 C31 H31A 118.8 . . ? C32 C31 H31A 118.8 . . ? C31 C32 C27 121.0(2) . . ? C31 C32 C35 115.8(2) . . ? C27 C32 C35 123.1(2) . . ? C28 C33 H33A 109.5 . . ? C28 C33 H33B 109.5 . . ? H33A C33 H33B 109.5 . . ? C28 C33 H33C 109.5 . . ? H33A C33 H33C 109.5 . . ? H33B C33 H33C 109.5 . . ? C30 C34 H34A 109.5 . . ? C30 C34 H34B 109.5 . . ? H34A C34 H34B 109.5 . . ? C30 C34 H34C 109.5 . . ? H34A C34 H34C 109.5 . . ? H34B C34 H34C 109.5 . . ? C32 C35 H35A 109.5 . . ? C32 C35 H35B 109.5 . . ? H35A C35 H35B 109.5 . . ? C32 C35 H35C 109.5 . . ? H35A C35 H35C 109.5 . . ? H35B C35 H35C 109.5 . . ? Cl1 C36 Cl2 112.6(2) . . ? Cl1 C36 H36A 109.1 . . ? Cl2 C36 H36A 109.1 . . ? Cl1 C36 H36B 109.1 . . ? Cl2 C36 H36B 109.1 . . ? H36A C36 H36B 107.8 . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.384 _refine_diff_density_min -0.458 _refine_diff_density_rms 0.048