# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_coden_Cambridge 182 loop_ _publ_author_name 'Junfa Wei' 'Zhanguo Chen' 'Yanni Gao' 'Xiaowei Jia' 'Xiaoyan Ma' 'Xianying Shi' _publ_contact_author_name 'Junfa Wei' _publ_contact_author_email WEIJF@SNNU.EDU.CN _publ_section_title ; A Novel Class of C3d Symmetrical Molecules Synthesized by a Six-Fold Substitution from 1,4,5,8,9,12-Hexabromododecahydrotriphenylene ; # Attachment 'xb19121.cif' data_xb1912 _database_code_depnum_ccdc_archive 'CCDC 770735' #TrackingRef 'xb19121.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H18 N18' _chemical_formula_weight 486.50 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 17.280(6) _cell_length_b 10.589(4) _cell_length_c 11.979(5) _cell_angle_alpha 90.00 _cell_angle_beta 94.513(8) _cell_angle_gamma 90.00 _cell_volume 2185.1(14) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 634 _cell_measurement_theta_min 0.00 _cell_measurement_theta_max 0.00 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.31 _exptl_crystal_size_mid 0.27 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.479 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1008 _exptl_absorpt_coefficient_mu 0.105 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.9684 _exptl_absorpt_correction_T_max 0.9863 _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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10780 _diffrn_reflns_av_R_equivalents 0.0761 _diffrn_reflns_av_sigmaI/netI 0.1299 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 1.18 _diffrn_reflns_theta_max 25.10 _reflns_number_total 3894 _reflns_number_gt 1402 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _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^)+(0.0329P)^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 none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3894 _refine_ls_number_parameters 325 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1492 _refine_ls_R_factor_gt 0.0508 _refine_ls_wR_factor_ref 0.1267 _refine_ls_wR_factor_gt 0.0989 _refine_ls_goodness_of_fit_ref 1.044 _refine_ls_restrained_S_all 1.044 _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 0.7356(2) 1.0536(4) -0.1083(3) 0.0936(13) Uani 1 1 d . . . N2 N 0.7357(2) 1.0292(3) -0.0160(3) 0.0640(10) Uani 1 1 d . . . N3 N 0.73290(19) 0.9895(3) 0.0792(3) 0.0639(10) Uani 1 1 d . . . N4 N 0.60976(18) 1.2109(3) 0.3785(3) 0.0590(9) Uani 1 1 d . . . N5 N 0.5564(2) 1.2846(3) 0.3557(3) 0.0645(10) Uani 1 1 d . . . N6 N 0.5091(2) 1.3582(4) 0.3417(4) 0.1075(16) Uani 1 1 d . . . N7 N 0.5956(2) 0.6741(4) 0.4032(4) 0.0931(14) Uani 1 1 d . . . N8 N 0.58091(19) 0.7691(4) 0.4373(3) 0.0640(11) Uani 1 1 d . . . N9 N 0.55676(18) 0.8708(3) 0.4720(3) 0.0628(10) Uani 1 1 d . . . N10 N 0.8415(2) 1.1252(4) 0.6485(4) 0.0946(14) Uani 1 1 d . . . N11 N 0.82836(19) 1.0213(4) 0.6585(3) 0.0600(10) Uani 1 1 d . . . N12 N 0.8203(2) 0.9093(3) 0.6779(3) 0.0664(10) Uani 1 1 d . . . N13 N 0.9407(3) 0.5124(4) 0.4035(5) 0.150(2) Uani 1 1 d . . . N14 N 0.9052(2) 0.5990(4) 0.4241(3) 0.0790(11) Uani 1 1 d . . . N15 N 0.8594(2) 0.6809(3) 0.4441(3) 0.0830(12) Uani 1 1 d . . . N16 N 0.9296(2) 1.0805(4) 0.2658(4) 0.1073(17) Uani 1 1 d . . . N17 N 0.9076(2) 1.1549(4) 0.3365(4) 0.0832(14) Uani 1 1 d . . . N18 N 0.8900(3) 1.2315(4) 0.3956(5) 0.131(2) Uani 1 1 d . . . C1 C 0.8140(2) 0.9553(3) 0.3160(3) 0.0394(9) Uani 1 1 d . . . C2 C 0.7465(2) 1.0222(3) 0.2788(3) 0.0369(9) Uani 1 1 d . . . C3 C 0.6829(2) 1.0248(3) 0.3436(3) 0.0409(9) Uani 1 1 d . . . C4 C 0.6873(2) 0.9614(3) 0.4478(3) 0.0411(9) Uani 1 1 d . . . C5 C 0.7541(2) 0.8969(3) 0.4861(3) 0.0385(9) Uani 1 1 d . . . C6 C 0.8175(2) 0.8923(3) 0.4189(3) 0.0408(9) Uani 1 1 d . . . C7 C 0.8887(2) 0.8130(3) 0.4567(3) 0.0481(10) Uani 1 1 d . . . H7 H 0.9020 0.8292 0.5365 0.058 Uiso 1 1 calc R . . C8 C 0.9600(2) 0.8378(4) 0.3943(3) 0.0630(12) Uani 1 1 d . . . H8A H 0.9853 0.9139 0.4237 0.076 Uiso 1 1 calc R . . H8B H 0.9961 0.7683 0.4074 0.076 Uiso 1 1 calc R . . C9 C 0.9416(2) 0.8527(3) 0.2720(3) 0.0558(11) Uani 1 1 d . . . H9A H 0.9200 0.7745 0.2410 0.067 Uiso 1 1 calc R . . H9B H 0.9888 0.8707 0.2363 0.067 Uiso 1 1 calc R . . C10 C 0.8839(2) 0.9589(3) 0.2479(3) 0.0547(11) Uani 1 1 d . . . H10 H 0.8653 0.9543 0.1686 0.066 Uiso 1 1 calc R . . C11 C 0.7448(2) 1.0912(3) 0.1670(3) 0.0461(10) Uani 1 1 d . . . H11 H 0.7951 1.1322 0.1601 0.055 Uiso 1 1 calc R . . C12 C 0.6810(2) 1.1891(3) 0.1543(3) 0.0549(11) Uani 1 1 d . . . H12A H 0.6939 1.2598 0.2038 0.066 Uiso 1 1 calc R . . H12B H 0.6761 1.2202 0.0779 0.066 Uiso 1 1 calc R . . C13 C 0.6051(2) 1.1313(3) 0.1828(3) 0.0582(11) Uani 1 1 d . . . H13A H 0.5941 1.0568 0.1372 0.070 Uiso 1 1 calc R . . H13B H 0.5633 1.1913 0.1670 0.070 Uiso 1 1 calc R . . C14 C 0.61016(19) 1.0957(3) 0.3056(3) 0.0461(10) Uani 1 1 d . . . H14 H 0.5652 1.0433 0.3195 0.055 Uiso 1 1 calc R . . C15 C 0.6172(2) 0.9624(3) 0.5167(3) 0.0504(10) Uani 1 1 d . . . H15 H 0.5942 1.0469 0.5101 0.060 Uiso 1 1 calc R . . C16 C 0.6376(2) 0.9380(3) 0.6405(3) 0.0571(11) Uani 1 1 d . . . H16A H 0.6648 1.0107 0.6735 0.068 Uiso 1 1 calc R . . H16B H 0.5903 0.9267 0.6779 0.068 Uiso 1 1 calc R . . C17 C 0.6880(2) 0.8222(3) 0.6584(3) 0.0566(11) Uani 1 1 d . . . H17A H 0.6601 0.7488 0.6281 0.068 Uiso 1 1 calc R . . H17B H 0.6998 0.8087 0.7381 0.068 Uiso 1 1 calc R . . C18 C 0.7632(2) 0.8371(3) 0.6019(3) 0.0480(10) Uani 1 1 d . . . H18 H 0.7846 0.7523 0.5931 0.058 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 0.142(4) 0.084(3) 0.056(3) 0.003(3) 0.018(3) 0.019(3) N2 0.087(3) 0.051(2) 0.055(2) -0.005(2) 0.015(2) 0.0134(19) N3 0.102(3) 0.052(2) 0.038(2) 0.0049(19) 0.014(2) 0.0067(19) N4 0.062(2) 0.054(2) 0.061(2) -0.0058(19) 0.0048(19) 0.0195(19) N5 0.073(3) 0.055(2) 0.068(3) 0.005(2) 0.017(2) 0.010(2) N6 0.104(4) 0.085(3) 0.135(4) 0.008(3) 0.016(3) 0.044(3) N7 0.078(3) 0.098(3) 0.104(4) -0.045(3) 0.016(2) -0.013(3) N8 0.049(3) 0.088(3) 0.056(3) -0.006(3) 0.0094(19) -0.017(3) N9 0.043(2) 0.071(3) 0.076(3) 0.001(2) 0.013(2) -0.003(2) N10 0.092(3) 0.074(3) 0.116(4) -0.016(3) -0.004(3) -0.010(3) N11 0.056(3) 0.073(3) 0.050(2) -0.017(3) 0.0001(18) 0.006(3) N12 0.087(3) 0.055(2) 0.056(2) 0.004(2) -0.001(2) 0.011(2) N13 0.127(5) 0.079(4) 0.249(7) -0.031(4) 0.041(4) 0.026(3) N14 0.087(4) 0.066(3) 0.085(3) 0.007(3) 0.015(2) 0.003(3) N15 0.083(3) 0.052(3) 0.119(3) 0.005(2) 0.039(2) 0.018(2) N16 0.080(3) 0.066(3) 0.184(5) 0.004(3) 0.059(3) -0.004(3) N17 0.080(4) 0.064(3) 0.104(4) 0.029(3) -0.003(3) -0.026(3) N18 0.188(5) 0.085(4) 0.119(5) -0.009(3) 0.002(4) -0.040(4) C1 0.043(3) 0.035(2) 0.041(2) -0.0019(19) 0.014(2) -0.0055(19) C2 0.039(2) 0.031(2) 0.041(2) 0.0044(18) 0.000(2) 0.0016(18) C3 0.043(3) 0.035(2) 0.045(2) -0.003(2) 0.004(2) 0.0005(19) C4 0.042(3) 0.039(2) 0.043(2) -0.001(2) 0.008(2) 0.005(2) C5 0.040(2) 0.041(2) 0.037(2) -0.0049(19) 0.012(2) -0.0032(19) C6 0.041(3) 0.034(2) 0.045(2) -0.003(2) -0.007(2) 0.0004(19) C7 0.052(3) 0.041(2) 0.051(3) -0.006(2) 0.006(2) -0.001(2) C8 0.047(3) 0.058(3) 0.084(3) 0.000(3) 0.011(3) 0.006(2) C9 0.055(3) 0.053(3) 0.062(3) 0.005(2) 0.021(2) 0.004(2) C10 0.055(3) 0.046(3) 0.065(3) 0.007(2) 0.016(2) -0.001(2) C11 0.058(3) 0.037(2) 0.044(2) -0.001(2) 0.009(2) -0.004(2) C12 0.073(3) 0.047(2) 0.045(2) 0.000(2) 0.000(2) 0.012(2) C13 0.045(3) 0.062(3) 0.066(3) 0.002(2) -0.006(2) 0.011(2) C14 0.042(2) 0.045(2) 0.050(3) 0.003(2) 0.000(2) 0.010(2) C15 0.048(3) 0.052(2) 0.053(3) 0.003(2) 0.012(2) 0.007(2) C16 0.057(3) 0.061(3) 0.056(3) 0.010(2) 0.022(2) 0.013(2) C17 0.063(3) 0.065(3) 0.046(2) 0.003(2) 0.023(2) -0.001(2) C18 0.062(3) 0.042(2) 0.039(2) -0.005(2) 0.000(2) 0.003(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 N2 1.136(4) . ? N2 N3 1.219(4) . ? N3 C11 1.508(4) . ? N4 N5 1.223(4) . ? N4 C14 1.501(4) . ? N5 N6 1.133(4) . ? N7 N8 1.122(4) . ? N8 N9 1.239(4) . ? N9 C15 1.493(4) . ? N10 N11 1.131(4) . ? N11 N12 1.219(4) . ? N12 C18 1.499(4) . ? N13 N14 1.141(5) . ? N14 N15 1.210(4) . ? N15 C7 1.492(4) . ? N16 N17 1.239(5) . ? N16 C10 1.517(5) . ? N17 N18 1.132(5) . ? C1 C6 1.398(4) . ? C1 C2 1.407(4) . ? C1 C10 1.510(4) . ? C2 C3 1.394(4) . ? C2 C11 1.524(4) . ? C3 C4 1.413(4) . ? C3 C14 1.504(4) . ? C4 C5 1.387(4) . ? C4 C15 1.520(4) . ? C5 C6 1.410(4) . ? C5 C18 1.522(4) . ? C6 C7 1.529(4) . ? C7 C8 1.513(4) . ? C7 H7 0.9800 . ? C8 C9 1.483(5) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 C10 1.516(4) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 H10 0.9800 . ? C11 C12 1.512(4) . ? C11 H11 0.9800 . ? C12 C13 1.510(4) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C13 C14 1.515(5) . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C14 H14 0.9800 . ? C15 C16 1.519(5) . ? C15 H15 0.9800 . ? C16 C17 1.510(4) . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? C17 C18 1.520(4) . ? C17 H17A 0.9700 . ? C17 H17B 0.9700 . ? C18 H18 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 N1 N2 N3 172.6(4) . . ? N2 N3 C11 113.1(3) . . ? N5 N4 C14 115.3(3) . . ? N6 N5 N4 174.6(4) . . ? N7 N8 N9 173.3(5) . . ? N8 N9 C15 116.2(3) . . ? N10 N11 N12 173.3(5) . . ? N11 N12 C18 117.4(3) . . ? N13 N14 N15 171.6(5) . . ? N14 N15 C7 118.0(4) . . ? N17 N16 C10 116.9(4) . . ? N18 N17 N16 173.8(5) . . ? C6 C1 C2 119.7(3) . . ? C6 C1 C10 120.5(3) . . ? C2 C1 C10 119.6(3) . . ? C3 C2 C1 120.3(3) . . ? C3 C2 C11 121.3(3) . . ? C1 C2 C11 118.5(3) . . ? C2 C3 C4 119.5(3) . . ? C2 C3 C14 121.2(3) . . ? C4 C3 C14 119.4(3) . . ? C5 C4 C3 120.8(3) . . ? C5 C4 C15 120.1(3) . . ? C3 C4 C15 119.1(3) . . ? C4 C5 C6 119.4(3) . . ? C4 C5 C18 122.0(3) . . ? C6 C5 C18 118.5(3) . . ? C1 C6 C5 120.3(3) . . ? C1 C6 C7 120.1(3) . . ? C5 C6 C7 119.5(3) . . ? N15 C7 C8 113.3(3) . . ? N15 C7 C6 103.1(3) . . ? C8 C7 C6 115.2(3) . . ? N15 C7 H7 108.3 . . ? C8 C7 H7 108.3 . . ? C6 C7 H7 108.3 . . ? C9 C8 C7 112.7(3) . . ? C9 C8 H8A 109.0 . . ? C7 C8 H8A 109.0 . . ? C9 C8 H8B 109.0 . . ? C7 C8 H8B 109.0 . . ? H8A C8 H8B 107.8 . . ? C8 C9 C10 110.7(3) . . ? C8 C9 H9A 109.5 . . ? C10 C9 H9A 109.5 . . ? C8 C9 H9B 109.5 . . ? C10 C9 H9B 109.5 . . ? H9A C9 H9B 108.1 . . ? C1 C10 C9 114.8(3) . . ? C1 C10 N16 112.0(3) . . ? C9 C10 N16 106.0(3) . . ? C1 C10 H10 107.9 . . ? C9 C10 H10 107.9 . . ? N16 C10 H10 107.9 . . ? N3 C11 C12 111.1(3) . . ? N3 C11 C2 105.3(3) . . ? C12 C11 C2 112.3(3) . . ? N3 C11 H11 109.3 . . ? C12 C11 H11 109.3 . . ? C2 C11 H11 109.3 . . ? C13 C12 C11 109.8(3) . . ? C13 C12 H12A 109.7 . . ? C11 C12 H12A 109.7 . . ? C13 C12 H12B 109.7 . . ? C11 C12 H12B 109.7 . . ? H12A C12 H12B 108.2 . . ? C12 C13 C14 109.6(3) . . ? C12 C13 H13A 109.7 . . ? C14 C13 H13A 109.7 . . ? C12 C13 H13B 109.7 . . ? C14 C13 H13B 109.7 . . ? H13A C13 H13B 108.2 . . ? N4 C14 C3 105.8(3) . . ? N4 C14 C13 111.1(3) . . ? C3 C14 C13 113.7(3) . . ? N4 C14 H14 108.7 . . ? C3 C14 H14 108.7 . . ? C13 C14 H14 108.7 . . ? N9 C15 C16 110.1(3) . . ? N9 C15 C4 111.4(3) . . ? C16 C15 C4 113.2(3) . . ? N9 C15 H15 107.3 . . ? C16 C15 H15 107.3 . . ? C4 C15 H15 107.3 . . ? C17 C16 C15 111.4(3) . . ? C17 C16 H16A 109.4 . . ? C15 C16 H16A 109.4 . . ? C17 C16 H16B 109.4 . . ? C15 C16 H16B 109.4 . . ? H16A C16 H16B 108.0 . . ? C16 C17 C18 110.8(3) . . ? C16 C17 H17A 109.5 . . ? C18 C17 H17A 109.5 . . ? C16 C17 H17B 109.5 . . ? C18 C17 H17B 109.5 . . ? H17A C17 H17B 108.1 . . ? N12 C18 C17 109.1(3) . . ? N12 C18 C5 111.0(3) . . ? C17 C18 C5 114.8(3) . . ? N12 C18 H18 107.2 . . ? C17 C18 H18 107.2 . . ? C5 C18 H18 107.2 . . ? 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 N1 N2 N3 C11 -171(3) . . . . ? C14 N4 N5 N6 176(5) . . . . ? N7 N8 N9 C15 -178(100) . . . . ? N10 N11 N12 C18 -175(4) . . . . ? N13 N14 N15 C7 -173(3) . . . . ? C10 N16 N17 N18 -150(6) . . . . ? C6 C1 C2 C3 -0.6(5) . . . . ? C10 C1 C2 C3 -176.8(3) . . . . ? C6 C1 C2 C11 179.3(3) . . . . ? C10 C1 C2 C11 3.1(5) . . . . ? C1 C2 C3 C4 1.0(5) . . . . ? C11 C2 C3 C4 -178.9(3) . . . . ? C1 C2 C3 C14 180.0(3) . . . . ? C11 C2 C3 C14 0.1(5) . . . . ? C2 C3 C4 C5 0.0(5) . . . . ? C14 C3 C4 C5 -178.9(3) . . . . ? C2 C3 C4 C15 -178.7(3) . . . . ? C14 C3 C4 C15 2.3(5) . . . . ? C3 C4 C5 C6 -1.5(5) . . . . ? C15 C4 C5 C6 177.3(3) . . . . ? C3 C4 C5 C18 174.8(3) . . . . ? C15 C4 C5 C18 -6.5(5) . . . . ? C2 C1 C6 C5 -0.8(5) . . . . ? C10 C1 C6 C5 175.3(3) . . . . ? C2 C1 C6 C7 176.4(3) . . . . ? C10 C1 C6 C7 -7.5(5) . . . . ? C4 C5 C6 C1 1.9(5) . . . . ? C18 C5 C6 C1 -174.5(3) . . . . ? C4 C5 C6 C7 -175.4(3) . . . . ? C18 C5 C6 C7 8.2(4) . . . . ? N14 N15 C7 C8 25.8(5) . . . . ? N14 N15 C7 C6 151.0(4) . . . . ? C1 C6 C7 N15 -107.6(4) . . . . ? C5 C6 C7 N15 69.7(4) . . . . ? C1 C6 C7 C8 16.4(4) . . . . ? C5 C6 C7 C8 -166.4(3) . . . . ? N15 C7 C8 C9 76.5(4) . . . . ? C6 C7 C8 C9 -41.9(4) . . . . ? C7 C8 C9 C10 57.6(4) . . . . ? C6 C1 C10 C9 23.5(5) . . . . ? C2 C1 C10 C9 -160.3(3) . . . . ? C6 C1 C10 N16 -97.5(4) . . . . ? C2 C1 C10 N16 78.7(4) . . . . ? C8 C9 C10 C1 -48.2(4) . . . . ? C8 C9 C10 N16 76.1(4) . . . . ? N17 N16 C10 C1 4.3(6) . . . . ? N17 N16 C10 C9 -121.7(5) . . . . ? N2 N3 C11 C12 63.0(4) . . . . ? N2 N3 C11 C2 -175.2(3) . . . . ? C3 C2 C11 N3 -103.7(4) . . . . ? C1 C2 C11 N3 76.4(4) . . . . ? C3 C2 C11 C12 17.4(4) . . . . ? C1 C2 C11 C12 -162.5(3) . . . . ? N3 C11 C12 C13 68.1(4) . . . . ? C2 C11 C12 C13 -49.5(4) . . . . ? C11 C12 C13 C14 65.5(4) . . . . ? N5 N4 C14 C3 176.2(3) . . . . ? N5 N4 C14 C13 52.4(4) . . . . ? C2 C3 C14 N4 -106.9(3) . . . . ? C4 C3 C14 N4 72.1(4) . . . . ? C2 C3 C14 C13 15.2(5) . . . . ? C4 C3 C14 C13 -165.8(3) . . . . ? C12 C13 C14 N4 71.8(4) . . . . ? C12 C13 C14 C3 -47.4(4) . . . . ? N8 N9 C15 C16 -88.0(4) . . . . ? N8 N9 C15 C4 38.5(4) . . . . ? C5 C4 C15 N9 -101.1(4) . . . . ? C3 C4 C15 N9 77.6(4) . . . . ? C5 C4 C15 C16 23.6(5) . . . . ? C3 C4 C15 C16 -157.7(3) . . . . ? N9 C15 C16 C17 75.3(4) . . . . ? C4 C15 C16 C17 -50.2(4) . . . . ? C15 C16 C17 C18 59.6(4) . . . . ? N11 N12 C18 C17 -100.3(4) . . . . ? N11 N12 C18 C5 27.1(5) . . . . ? C16 C17 C18 N12 83.5(4) . . . . ? C16 C17 C18 C5 -41.7(4) . . . . ? C4 C5 C18 N12 -108.5(4) . . . . ? C6 C5 C18 N12 67.8(4) . . . . ? C4 C5 C18 C17 15.8(5) . . . . ? C6 C5 C18 C17 -167.9(3) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.10 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.230 _refine_diff_density_min -0.211 _refine_diff_density_rms 0.049 # Attachment 'z1.cif' data_z _database_code_depnum_ccdc_archive 'CCDC 770736' #TrackingRef 'z1.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C54 H42 Cl6 N0 O0 S6' _chemical_formula_sum 'C54 H42 Cl6 N0 O0 S6' _chemical_formula_weight 1095.94 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' O O 0.0106 0.0060 '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' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 11.5162(16) _cell_length_b 14.2283(19) _cell_length_c 17.692(2) _cell_angle_alpha 100.364(2) _cell_angle_beta 108.708(2) _cell_angle_gamma 102.865(2) _cell_volume 2575.8(6) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 5404 _cell_measurement_theta_min 2.55 _cell_measurement_theta_max 27.99 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.413 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1128 _exptl_absorpt_coefficient_mu 0.614 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9300 _exptl_absorpt_correction_T_max 0.9525 _exptl_absorpt_process_details '(SADABS; Bruker, 2001)' _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 'Bruker APEXII CCD' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% ? _diffrn_reflns_number 13338 _diffrn_reflns_av_R_equivalents 0.0184 _diffrn_reflns_av_sigmaI/netI 0.0334 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 1.89 _diffrn_reflns_theta_max 25.00 _reflns_number_total 9021 _reflns_number_gt 7057 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'APEX2 (Bruker, 2004)' _computing_cell_refinement 'SAINT-Plus (Bruker, 2001)' _computing_data_reduction SAINT-Plus _computing_structure_solution 'SHELXS97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 2008)' _computing_publication_material 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^)+(0.1200P)^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 noref _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 9021 _refine_ls_number_parameters 595 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0571 _refine_ls_R_factor_gt 0.0428 _refine_ls_wR_factor_ref 0.1619 _refine_ls_wR_factor_gt 0.1437 _refine_ls_goodness_of_fit_ref 1.001 _refine_ls_restrained_S_all 1.001 _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 C1 C 0.5978(4) 0.9528(3) -0.1043(2) 0.0776(11) Uani 1 1 d . . . C2 C 0.5654(5) 0.8525(3) -0.1354(2) 0.0943(14) Uani 1 1 d . . . H2 H 0.5350 0.8240 -0.1923 0.113 Uiso 1 1 calc R . . C3 C 0.5781(4) 0.7930(3) -0.0815(2) 0.0759(10) Uani 1 1 d . . . H3 H 0.5589 0.7242 -0.1025 0.091 Uiso 1 1 calc R . . C4 C 0.6182(3) 0.8328(2) 0.00211(16) 0.0459(6) Uani 1 1 d . . . C5 C 0.6442(5) 0.9350(3) 0.0317(2) 0.0913(14) Uani 1 1 d . . . H5 H 0.6687 0.9636 0.0881 0.110 Uiso 1 1 calc R . . C6 C 0.6344(5) 0.9950(3) -0.0217(3) 0.1092(18) Uani 1 1 d . . . H6 H 0.6526 1.0638 -0.0014 0.131 Uiso 1 1 calc R . . C7 C 1.3274(3) 0.5614(2) 0.11880(18) 0.0541(7) Uani 1 1 d . . . C8 C 1.2372(3) 0.5006(2) 0.1378(2) 0.0622(8) Uani 1 1 d . . . H8 H 1.2292 0.4326 0.1298 0.075 Uiso 1 1 calc R . . C9 C 1.1578(3) 0.5412(2) 0.1692(2) 0.0567(8) Uani 1 1 d . . . H9 H 1.0984 0.5007 0.1840 0.068 Uiso 1 1 calc R . . C10 C 1.1662(2) 0.6418(2) 0.17867(16) 0.0420(6) Uani 1 1 d . . . C11 C 1.2547(3) 0.7007(2) 0.1561(2) 0.0556(7) Uani 1 1 d . . . H11 H 1.2595 0.7676 0.1604 0.067 Uiso 1 1 calc R . . C12 C 1.3366(3) 0.6605(2) 0.1271(2) 0.0629(8) Uani 1 1 d . . . H12 H 1.3977 0.7009 0.1133 0.075 Uiso 1 1 calc R . . C13 C 0.9182(3) 0.1852(3) 0.1076(2) 0.0649(9) Uani 1 1 d . . . C14 C 0.8626(3) 0.1790(2) 0.16472(19) 0.0608(8) Uani 1 1 d . . . H14 H 0.8638 0.1277 0.1907 0.073 Uiso 1 1 calc R . . C15 C 0.8042(3) 0.2506(2) 0.18338(17) 0.0520(7) Uani 1 1 d . . . H15 H 0.7654 0.2465 0.2219 0.062 Uiso 1 1 calc R . . C16 C 0.8026(3) 0.32809(19) 0.14584(16) 0.0462(6) Uani 1 1 d . . . C17 C 0.8568(4) 0.3303(2) 0.0865(2) 0.0682(9) Uani 1 1 d . . . H17 H 0.8538 0.3799 0.0588 0.082 Uiso 1 1 calc R . . C18 C 0.9159(4) 0.2587(3) 0.0681(2) 0.0805(11) Uani 1 1 d . . . H18 H 0.9536 0.2611 0.0290 0.097 Uiso 1 1 calc R . . C19 C 0.7049(5) 0.6519(3) 0.6762(2) 0.0783(11) Uani 1 1 d . . . C20 C 0.6629(5) 0.5713(3) 0.6093(2) 0.0878(13) Uani 1 1 d . . . H20 H 0.5936 0.5170 0.6012 0.105 Uiso 1 1 calc R . . C21 C 0.7239(4) 0.5704(2) 0.5532(2) 0.0759(11) Uani 1 1 d . . . H21 H 0.6954 0.5148 0.5077 0.091 Uiso 1 1 calc R . . C22 C 0.8264(3) 0.6506(2) 0.56368(16) 0.0518(7) Uani 1 1 d . . . C23 C 0.8679(4) 0.7311(3) 0.63280(19) 0.0736(10) Uani 1 1 d . . . H23 H 0.9369 0.7858 0.6413 0.088 Uiso 1 1 calc R . . C24 C 0.8089(4) 0.7317(4) 0.6892(2) 0.0875(12) Uani 1 1 d . . . H24 H 0.8391 0.7857 0.7359 0.105 Uiso 1 1 calc R . . C25 C 0.3524(3) 0.7539(2) 0.55542(18) 0.0492(7) Uani 1 1 d . . . C26 C 0.4834(3) 0.7792(2) 0.57796(17) 0.0539(7) Uani 1 1 d . . . H26 H 0.5373 0.8137 0.6324 0.065 Uiso 1 1 calc R . . C27 C 0.5351(3) 0.7534(2) 0.51950(16) 0.0496(7) Uani 1 1 d . . . H27 H 0.6239 0.7695 0.5351 0.060 Uiso 1 1 calc R . . C28 C 0.4555(2) 0.70341(19) 0.43772(15) 0.0386(6) Uani 1 1 d . . . C29 C 0.3237(3) 0.6771(2) 0.41659(17) 0.0462(6) Uani 1 1 d . . . H29 H 0.2691 0.6423 0.3623 0.055 Uiso 1 1 calc R . . C30 C 0.2722(3) 0.7019(2) 0.47559(19) 0.0530(7) Uani 1 1 d . . . H30 H 0.1836 0.6834 0.4610 0.064 Uiso 1 1 calc R . . C31 C 1.2222(3) 0.9429(2) 0.3757(2) 0.0608(8) Uani 1 1 d . . . C32 C 1.1765(3) 0.9838(2) 0.3121(2) 0.0636(8) Uani 1 1 d . . . H32 H 1.2270 1.0044 0.2829 0.076 Uiso 1 1 calc R . . C33 C 1.0539(3) 0.9941(2) 0.2916(2) 0.0560(7) Uani 1 1 d . . . H33 H 1.0217 1.0204 0.2476 0.067 Uiso 1 1 calc R . . C34 C 0.9795(3) 0.96585(19) 0.33605(17) 0.0457(6) Uani 1 1 d . . . C35 C 1.0276(3) 0.9242(2) 0.40063(18) 0.0536(7) Uani 1 1 d . . . H35 H 0.9782 0.9041 0.4307 0.064 Uiso 1 1 calc R . . C36 C 1.1493(3) 0.9127(2) 0.4199(2) 0.0609(8) Uani 1 1 d . . . H36 H 1.1815 0.8846 0.4627 0.073 Uiso 1 1 calc R . . C37 C 0.9104(2) 0.6422(2) 0.15766(15) 0.0397(6) Uani 1 1 d . . . H37 H 0.8924 0.5694 0.1399 0.048 Uiso 1 1 calc R . . C38 C 0.8812(3) 0.6820(2) 0.08155(16) 0.0467(6) Uani 1 1 d . . . H38A H 0.9438 0.6756 0.0566 0.056 Uiso 1 1 calc R . . H38B H 0.7968 0.6424 0.0411 0.056 Uiso 1 1 calc R . . C39 C 0.8853(3) 0.7907(2) 0.10446(17) 0.0495(7) Uani 1 1 d . . . H39A H 0.8657 0.8142 0.0550 0.059 Uiso 1 1 calc R . . H39B H 0.9712 0.8308 0.1426 0.059 Uiso 1 1 calc R . . C40 C 0.7897(2) 0.8036(2) 0.14446(15) 0.0404(6) Uani 1 1 d . . . H40 H 0.8064 0.8752 0.1684 0.048 Uiso 1 1 calc R . . C41 C 0.7909(2) 0.74962(18) 0.21155(14) 0.0351(5) Uani 1 1 d . . . C42 C 0.8360(2) 0.66645(18) 0.21208(14) 0.0350(5) Uani 1 1 d . . . C43 C 0.8244(2) 0.60977(17) 0.26847(14) 0.0349(5) Uani 1 1 d . . . C44 C 0.8618(3) 0.51274(19) 0.26124(15) 0.0415(6) Uani 1 1 d . . . H44 H 0.9405 0.5240 0.2494 0.050 Uiso 1 1 calc R . . C45 C 0.8850(3) 0.4764(2) 0.33912(17) 0.0483(7) Uani 1 1 d . . . H45A H 0.8914 0.4089 0.3272 0.058 Uiso 1 1 calc R . . H45B H 0.9655 0.5194 0.3822 0.058 Uiso 1 1 calc R . . C46 C 0.7760(3) 0.4774(2) 0.36924(17) 0.0490(7) Uani 1 1 d . . . H46A H 0.7895 0.4508 0.4171 0.059 Uiso 1 1 calc R . . H46B H 0.6954 0.4350 0.3259 0.059 Uiso 1 1 calc R . . C47 C 0.7687(3) 0.58383(18) 0.39269(15) 0.0396(6) Uani 1 1 d . . . H47 H 0.6876 0.5803 0.4007 0.047 Uiso 1 1 calc R . . C48 C 0.7737(2) 0.64008(17) 0.32734(14) 0.0350(5) Uani 1 1 d . . . C49 C 0.7304(2) 0.72597(17) 0.32875(14) 0.0336(5) Uani 1 1 d . . . C50 C 0.7387(2) 0.78076(17) 0.27127(14) 0.0343(5) Uani 1 1 d . . . C51 C 0.6965(2) 0.87397(19) 0.27219(16) 0.0404(6) Uani 1 1 d . . . H51 H 0.6470 0.8704 0.2146 0.049 Uiso 1 1 calc R . . C52 C 0.6733(2) 0.75764(18) 0.39272(15) 0.0361(5) Uani 1 1 d . . . H52 H 0.7252 0.7503 0.4461 0.043 Uiso 1 1 calc R . . C53 C 0.6108(3) 0.8854(2) 0.32125(17) 0.0441(6) Uani 1 1 d . . . H53A H 0.6031 0.9526 0.3294 0.053 Uiso 1 1 calc R . . H53B H 0.5256 0.8384 0.2906 0.053 Uiso 1 1 calc R . . C54 C 0.6684(3) 0.86567(19) 0.40470(16) 0.0408(6) Uani 1 1 d . . . H54A H 0.7546 0.9115 0.4346 0.049 Uiso 1 1 calc R . . H54B H 0.6169 0.8772 0.4373 0.049 Uiso 1 1 calc R . . Cl1 Cl 1.37472(9) 0.92979(9) 0.40009(9) 0.1031(4) Uani 1 1 d . . . Cl2 Cl 1.43488(10) 0.51195(8) 0.08718(8) 0.0946(4) Uani 1 1 d . . . Cl3 Cl 0.99361(14) 0.09597(10) 0.08485(8) 0.1145(4) Uani 1 1 d . . . Cl4 Cl 0.62342(16) 0.65526(12) 0.74393(8) 0.1225(5) Uani 1 1 d . . . Cl5 Cl 0.28732(10) 0.79086(7) 0.62826(6) 0.0768(3) Uani 1 1 d . . . Cl6 Cl 0.58405(15) 1.02850(11) -0.17290(9) 0.1349(6) Uani 1 1 d . . . S1 S 0.62209(7) 0.75102(5) 0.06677(4) 0.04719(19) Uani 1 1 d . . . S2 S 1.07959(7) 0.69920(6) 0.22989(4) 0.0489(2) Uani 1 1 d . . . S3 S 0.72843(8) 0.42041(5) 0.16967(5) 0.0547(2) Uani 1 1 d . . . S4 S 0.90349(7) 0.65792(6) 0.49182(4) 0.0510(2) Uani 1 1 d . . . S5 S 0.50970(6) 0.66885(5) 0.35634(4) 0.04357(19) Uani 1 1 d . . . S6 S 0.83208(7) 0.99453(5) 0.31544(5) 0.0553(2) Uani 1 1 d . . . 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 C1 0.076(2) 0.081(3) 0.072(2) 0.050(2) 0.0098(19) 0.020(2) C2 0.154(4) 0.089(3) 0.054(2) 0.035(2) 0.038(2) 0.052(3) C3 0.119(3) 0.059(2) 0.0532(19) 0.0178(16) 0.032(2) 0.032(2) C4 0.0458(15) 0.0491(16) 0.0441(15) 0.0186(12) 0.0138(12) 0.0168(12) C5 0.141(4) 0.051(2) 0.0534(19) 0.0145(16) 0.003(2) 0.025(2) C6 0.142(4) 0.049(2) 0.088(3) 0.030(2) -0.014(3) 0.012(2) C7 0.0430(15) 0.0586(18) 0.0603(17) 0.0029(14) 0.0245(14) 0.0177(13) C8 0.069(2) 0.0467(17) 0.080(2) 0.0107(15) 0.0391(18) 0.0240(15) C9 0.0592(18) 0.0472(16) 0.078(2) 0.0181(15) 0.0415(16) 0.0184(14) C10 0.0364(13) 0.0488(15) 0.0429(14) 0.0084(11) 0.0165(11) 0.0177(11) C11 0.0542(17) 0.0469(16) 0.075(2) 0.0183(15) 0.0340(16) 0.0168(13) C12 0.0544(18) 0.062(2) 0.084(2) 0.0197(17) 0.0427(17) 0.0146(15) C13 0.078(2) 0.0573(19) 0.0627(19) 0.0005(16) 0.0317(17) 0.0304(17) C14 0.085(2) 0.0487(17) 0.0552(17) 0.0148(14) 0.0283(17) 0.0291(16) C15 0.072(2) 0.0442(16) 0.0470(15) 0.0113(12) 0.0318(14) 0.0188(14) C16 0.0624(17) 0.0348(13) 0.0401(14) 0.0054(11) 0.0213(13) 0.0135(12) C17 0.106(3) 0.0498(18) 0.0614(19) 0.0165(15) 0.0490(19) 0.0215(18) C18 0.118(3) 0.067(2) 0.082(2) 0.0141(19) 0.073(2) 0.028(2) C19 0.128(4) 0.094(3) 0.0529(19) 0.039(2) 0.052(2) 0.067(3) C20 0.160(4) 0.055(2) 0.092(3) 0.037(2) 0.089(3) 0.039(2) C21 0.142(3) 0.0409(17) 0.070(2) 0.0229(15) 0.068(2) 0.028(2) C22 0.077(2) 0.0511(17) 0.0407(14) 0.0213(13) 0.0243(14) 0.0353(15) C23 0.074(2) 0.081(2) 0.0468(17) -0.0035(16) 0.0132(17) 0.0189(19) C24 0.098(3) 0.107(3) 0.0411(18) -0.0080(19) 0.0133(19) 0.040(3) C25 0.0677(19) 0.0451(15) 0.0595(17) 0.0234(13) 0.0428(15) 0.0285(14) C26 0.0613(18) 0.0666(19) 0.0423(15) 0.0150(13) 0.0254(14) 0.0268(15) C27 0.0472(16) 0.0677(19) 0.0413(15) 0.0158(13) 0.0217(13) 0.0231(14) C28 0.0455(14) 0.0406(14) 0.0396(13) 0.0164(11) 0.0220(11) 0.0185(11) C29 0.0436(15) 0.0465(15) 0.0516(15) 0.0133(12) 0.0219(13) 0.0138(12) C30 0.0464(16) 0.0525(17) 0.073(2) 0.0196(15) 0.0346(15) 0.0186(13) C31 0.0392(15) 0.0424(16) 0.083(2) 0.0007(15) 0.0089(15) 0.0125(13) C32 0.0498(18) 0.0577(19) 0.091(2) 0.0183(17) 0.0366(17) 0.0169(15) C33 0.0526(17) 0.0475(16) 0.0728(19) 0.0214(15) 0.0272(15) 0.0150(13) C34 0.0467(15) 0.0330(13) 0.0576(16) 0.0103(12) 0.0203(13) 0.0128(11) C35 0.0625(19) 0.0457(16) 0.0549(17) 0.0133(13) 0.0249(15) 0.0168(14) C36 0.064(2) 0.0499(17) 0.0581(18) 0.0101(14) 0.0069(16) 0.0243(15) C37 0.0432(14) 0.0433(14) 0.0396(13) 0.0101(11) 0.0215(11) 0.0183(11) C38 0.0489(15) 0.0602(17) 0.0417(14) 0.0159(12) 0.0268(12) 0.0208(13) C39 0.0507(16) 0.0629(18) 0.0512(16) 0.0285(14) 0.0293(13) 0.0224(14) C40 0.0441(14) 0.0451(14) 0.0409(13) 0.0185(11) 0.0207(11) 0.0181(12) C41 0.0344(12) 0.0396(13) 0.0358(12) 0.0144(10) 0.0150(10) 0.0135(10) C42 0.0371(13) 0.0373(13) 0.0342(12) 0.0080(10) 0.0169(10) 0.0141(10) C43 0.0391(13) 0.0331(12) 0.0367(12) 0.0094(10) 0.0168(10) 0.0151(10) C44 0.0476(15) 0.0391(14) 0.0435(14) 0.0111(11) 0.0198(12) 0.0199(11) C45 0.0647(18) 0.0378(14) 0.0512(15) 0.0174(12) 0.0229(14) 0.0262(13) C46 0.0704(19) 0.0370(14) 0.0507(16) 0.0192(12) 0.0302(14) 0.0207(13) C47 0.0482(15) 0.0358(13) 0.0402(13) 0.0149(11) 0.0210(11) 0.0132(11) C48 0.0376(13) 0.0340(12) 0.0371(12) 0.0126(10) 0.0158(10) 0.0130(10) C49 0.0348(12) 0.0347(12) 0.0340(12) 0.0094(10) 0.0153(10) 0.0121(10) C50 0.0353(12) 0.0333(12) 0.0385(13) 0.0113(10) 0.0165(10) 0.0130(10) C51 0.0401(14) 0.0419(14) 0.0492(14) 0.0183(12) 0.0214(12) 0.0199(11) C52 0.0381(13) 0.0370(13) 0.0386(13) 0.0107(10) 0.0196(11) 0.0134(10) C53 0.0470(15) 0.0430(14) 0.0578(16) 0.0194(12) 0.0278(13) 0.0266(12) C54 0.0441(14) 0.0384(14) 0.0456(14) 0.0086(11) 0.0234(12) 0.0163(11) Cl1 0.0484(5) 0.0875(7) 0.1645(11) 0.0312(7) 0.0235(6) 0.0303(5) Cl2 0.0769(6) 0.0854(7) 0.1379(9) 0.0034(6) 0.0701(6) 0.0329(5) Cl3 0.1439(11) 0.1141(9) 0.1147(9) 0.0119(7) 0.0650(8) 0.0854(9) Cl4 0.2001(15) 0.1585(12) 0.0959(8) 0.0688(8) 0.1083(10) 0.1144(12) Cl5 0.1016(7) 0.0769(6) 0.0876(6) 0.0228(5) 0.0718(6) 0.0405(5) Cl6 0.1379(11) 0.1361(11) 0.1328(10) 0.1061(10) 0.0212(9) 0.0338(9) S1 0.0464(4) 0.0523(4) 0.0489(4) 0.0231(3) 0.0201(3) 0.0155(3) S2 0.0437(4) 0.0546(4) 0.0493(4) 0.0041(3) 0.0204(3) 0.0202(3) S3 0.0606(5) 0.0438(4) 0.0540(4) 0.0057(3) 0.0146(4) 0.0213(3) S4 0.0564(4) 0.0537(4) 0.0438(4) 0.0167(3) 0.0171(3) 0.0178(3) S5 0.0433(4) 0.0488(4) 0.0384(3) 0.0069(3) 0.0209(3) 0.0090(3) S6 0.0553(4) 0.0369(4) 0.0913(6) 0.0261(4) 0.0391(4) 0.0232(3) _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 C1 C2 1.352(6) . ? C1 C6 1.362(6) . ? C1 Cl6 1.755(3) . ? C2 C3 1.380(5) . ? C2 H2 0.9300 . ? C3 C4 1.366(4) . ? C3 H3 0.9300 . ? C4 C5 1.382(4) . ? C4 S1 1.770(3) . ? C5 C6 1.377(5) . ? C5 H5 0.9300 . ? C6 H6 0.9300 . ? C7 C12 1.368(4) . ? C7 C8 1.367(4) . ? C7 Cl2 1.741(3) . ? C8 C9 1.387(4) . ? C8 H8 0.9300 . ? C9 C10 1.388(4) . ? C9 H9 0.9300 . ? C10 C11 1.379(4) . ? C10 S2 1.778(3) . ? C11 C12 1.388(4) . ? C11 H11 0.9300 . ? C12 H12 0.9300 . ? C13 C18 1.357(5) . ? C13 C14 1.365(5) . ? C13 Cl3 1.749(3) . ? C14 C15 1.387(4) . ? C14 H14 0.9300 . ? C15 C16 1.386(4) . ? C15 H15 0.9300 . ? C16 C17 1.385(4) . ? C16 S3 1.779(3) . ? C17 C18 1.392(5) . ? C17 H17 0.9300 . ? C18 H18 0.9300 . ? C19 C24 1.378(6) . ? C19 C20 1.360(5) . ? C19 Cl4 1.744(4) . ? C20 C21 1.388(5) . ? C20 H20 0.9300 . ? C21 C22 1.384(5) . ? C21 H21 0.9300 . ? C22 C23 1.383(4) . ? C22 S4 1.773(3) . ? C23 C24 1.375(5) . ? C23 H23 0.9300 . ? C24 H24 0.9300 . ? C25 C26 1.373(4) . ? C25 C30 1.370(4) . ? C25 Cl5 1.746(3) . ? C26 C27 1.384(4) . ? C26 H26 0.9300 . ? C27 C28 1.389(4) . ? C27 H27 0.9300 . ? C28 C29 1.384(4) . ? C28 S5 1.779(2) . ? C29 C30 1.387(4) . ? C29 H29 0.9300 . ? C30 H30 0.9300 . ? C31 C32 1.368(5) . ? C31 C36 1.372(5) . ? C31 Cl1 1.731(3) . ? C32 C33 1.389(4) . ? C32 H32 0.9300 . ? C33 C34 1.381(4) . ? C33 H33 0.9300 . ? C34 C35 1.396(4) . ? C34 S6 1.774(3) . ? C35 C36 1.386(4) . ? C35 H35 0.9300 . ? C36 H36 0.9300 . ? C37 C38 1.521(4) . ? C37 C42 1.524(3) . ? C37 S2 1.848(3) . ? C37 H37 0.9800 . ? C38 C39 1.513(4) . ? C38 H38A 0.9700 . ? C38 H38B 0.9700 . ? C39 C40 1.514(3) . ? C39 H39A 0.9700 . ? C39 H39B 0.9700 . ? C40 C41 1.523(3) . ? C40 S1 1.860(3) . ? C40 H40 0.9800 . ? C41 C42 1.394(3) . ? C41 C50 1.425(3) . ? C42 C43 1.411(3) . ? C43 C48 1.397(3) . ? C43 C44 1.531(3) . ? C44 C45 1.523(4) . ? C44 S3 1.857(3) . ? C44 H44 0.9800 . ? C45 C46 1.514(4) . ? C45 H45A 0.9700 . ? C45 H45B 0.9700 . ? C46 C47 1.525(4) . ? C46 H46A 0.9700 . ? C46 H46B 0.9700 . ? C47 C48 1.528(3) . ? C47 S4 1.859(3) . ? C47 H47 0.9800 . ? C48 C49 1.418(3) . ? C49 C50 1.402(3) . ? C49 C52 1.530(3) . ? C50 C51 1.510(3) . ? C51 C53 1.524(3) . ? C51 S6 1.880(3) . ? C51 H51 0.9800 . ? C52 C54 1.530(3) . ? C52 S5 1.852(2) . ? C52 H52 0.9800 . ? C53 C54 1.517(4) . ? C53 H53A 0.9700 . ? C53 H53B 0.9700 . ? C54 H54A 0.9700 . ? C54 H54B 0.9700 . ? 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 C2 C1 C6 121.1(3) . . ? C2 C1 Cl6 119.0(3) . . ? C6 C1 Cl6 119.8(3) . . ? C1 C2 C3 119.1(3) . . ? C1 C2 H2 120.5 . . ? C3 C2 H2 120.5 . . ? C2 C3 C4 121.5(3) . . ? C2 C3 H3 119.2 . . ? C4 C3 H3 119.2 . . ? C5 C4 C3 118.0(3) . . ? C5 C4 S1 122.8(2) . . ? C3 C4 S1 119.0(2) . . ? C4 C5 C6 120.7(3) . . ? C4 C5 H5 119.7 . . ? C6 C5 H5 119.7 . . ? C5 C6 C1 119.4(4) . . ? C5 C6 H6 120.3 . . ? C1 C6 H6 120.3 . . ? C12 C7 C8 120.9(3) . . ? C12 C7 Cl2 120.0(2) . . ? C8 C7 Cl2 119.0(2) . . ? C7 C8 C9 119.3(3) . . ? C7 C8 H8 120.4 . . ? C9 C8 H8 120.4 . . ? C8 C9 C10 120.7(3) . . ? C8 C9 H9 119.6 . . ? C10 C9 H9 119.6 . . ? C11 C10 C9 118.8(3) . . ? C11 C10 S2 119.2(2) . . ? C9 C10 S2 121.6(2) . . ? C10 C11 C12 120.3(3) . . ? C10 C11 H11 119.8 . . ? C12 C11 H11 119.8 . . ? C7 C12 C11 119.8(3) . . ? C7 C12 H12 120.1 . . ? C11 C12 H12 120.1 . . ? C18 C13 C14 121.5(3) . . ? C18 C13 Cl3 119.6(3) . . ? C14 C13 Cl3 118.9(3) . . ? C15 C14 C13 118.8(3) . . ? C15 C14 H14 120.6 . . ? C13 C14 H14 120.6 . . ? C14 C15 C16 121.4(3) . . ? C14 C15 H15 119.3 . . ? C16 C15 H15 119.3 . . ? C17 C16 C15 118.1(3) . . ? C17 C16 S3 120.2(2) . . ? C15 C16 S3 121.6(2) . . ? C16 C17 C18 120.4(3) . . ? C16 C17 H17 119.8 . . ? C18 C17 H17 119.8 . . ? C13 C18 C17 119.8(3) . . ? C13 C18 H18 120.1 . . ? C17 C18 H18 120.1 . . ? C24 C19 C20 120.3(3) . . ? C24 C19 Cl4 120.2(3) . . ? C20 C19 Cl4 119.4(4) . . ? C19 C20 C21 119.6(4) . . ? C19 C20 H20 120.2 . . ? C21 C20 H20 120.2 . . ? C22 C21 C20 121.2(3) . . ? C22 C21 H21 119.4 . . ? C20 C21 H21 119.4 . . ? C21 C22 C23 117.9(3) . . ? C21 C22 S4 123.8(2) . . ? C23 C22 S4 118.3(3) . . ? C22 C23 C24 121.1(4) . . ? C22 C23 H23 119.5 . . ? C24 C23 H23 119.5 . . ? C19 C24 C23 119.9(3) . . ? C19 C24 H24 120.1 . . ? C23 C24 H24 120.1 . . ? C26 C25 C30 120.5(3) . . ? C26 C25 Cl5 119.8(2) . . ? C30 C25 Cl5 119.7(2) . . ? C25 C26 C27 119.9(3) . . ? C25 C26 H26 120.1 . . ? C27 C26 H26 120.0 . . ? C26 C27 C28 120.5(3) . . ? C26 C27 H27 119.8 . . ? C28 C27 H27 119.8 . . ? C29 C28 C27 118.7(2) . . ? C29 C28 S5 116.42(19) . . ? C27 C28 S5 124.9(2) . . ? C28 C29 C30 120.6(3) . . ? C28 C29 H29 119.7 . . ? C30 C29 H29 119.7 . . ? C25 C30 C29 119.8(3) . . ? C25 C30 H30 120.1 . . ? C29 C30 H30 120.1 . . ? C32 C31 C36 121.1(3) . . ? C32 C31 Cl1 118.9(3) . . ? C36 C31 Cl1 120.0(3) . . ? C31 C32 C33 119.5(3) . . ? C31 C32 H32 120.3 . . ? C33 C32 H32 120.3 . . ? C34 C33 C32 120.6(3) . . ? C34 C33 H33 119.7 . . ? C32 C33 H33 119.7 . . ? C33 C34 C35 119.2(3) . . ? C33 C34 S6 118.6(2) . . ? C35 C34 S6 121.9(2) . . ? C36 C35 C34 119.9(3) . . ? C36 C35 H35 120.0 . . ? C34 C35 H35 120.1 . . ? C35 C36 C31 119.8(3) . . ? C35 C36 H36 120.1 . . ? C31 C36 H36 120.1 . . ? C38 C37 C42 114.5(2) . . ? C38 C37 S2 112.03(18) . . ? C42 C37 S2 102.82(16) . . ? C38 C37 H37 109.1 . . ? C42 C37 H37 109.1 . . ? S2 C37 H37 109.1 . . ? C39 C38 C37 110.9(2) . . ? C39 C38 H38A 109.5 . . ? C37 C38 H38A 109.5 . . ? C39 C38 H38B 109.5 . . ? C37 C38 H38B 109.5 . . ? H38A C38 H38B 108.0 . . ? C38 C39 C40 110.9(2) . . ? C38 C39 H39A 109.5 . . ? C40 C39 H39A 109.5 . . ? C38 C39 H39B 109.5 . . ? C40 C39 H39B 109.5 . . ? H39A C39 H39B 108.0 . . ? C39 C40 C41 114.9(2) . . ? C39 C40 S1 110.91(18) . . ? C41 C40 S1 104.35(16) . . ? C39 C40 H40 108.8 . . ? C41 C40 H40 108.8 . . ? S1 C40 H40 108.8 . . ? C42 C41 C50 119.7(2) . . ? C42 C41 C40 120.4(2) . . ? C50 C41 C40 119.7(2) . . ? C41 C42 C43 120.6(2) . . ? C41 C42 C37 120.0(2) . . ? C43 C42 C37 119.1(2) . . ? C48 C43 C42 119.9(2) . . ? C48 C43 C44 120.9(2) . . ? C42 C43 C44 119.1(2) . . ? C45 C44 C43 113.7(2) . . ? C45 C44 S3 112.22(19) . . ? C43 C44 S3 105.12(17) . . ? C45 C44 H44 108.6 . . ? C43 C44 H44 108.6 . . ? S3 C44 H44 108.6 . . ? C46 C45 C44 110.3(2) . . ? C46 C45 H45A 109.6 . . ? C44 C45 H45A 109.6 . . ? C46 C45 H45B 109.6 . . ? C44 C45 H45B 109.6 . . ? H45A C45 H45B 108.1 . . ? C45 C46 C47 110.5(2) . . ? C45 C46 H46A 109.5 . . ? C47 C46 H46A 109.6 . . ? C45 C46 H46B 109.6 . . ? C47 C46 H46B 109.6 . . ? H46A C46 H46B 108.1 . . ? C46 C47 C48 113.8(2) . . ? C46 C47 S4 110.07(18) . . ? C48 C47 S4 107.92(16) . . ? C46 C47 H47 108.3 . . ? C48 C47 H47 108.3 . . ? S4 C47 H47 108.3 . . ? C43 C48 C49 120.0(2) . . ? C43 C48 C47 120.7(2) . . ? C49 C48 C47 119.2(2) . . ? C50 C49 C48 120.1(2) . . ? C50 C49 C52 120.3(2) . . ? C48 C49 C52 119.6(2) . . ? C49 C50 C41 119.6(2) . . ? C49 C50 C51 121.6(2) . . ? C41 C50 C51 118.8(2) . . ? C53 C51 C50 114.4(2) . . ? C53 C51 S6 105.39(18) . . ? C50 C51 S6 114.48(17) . . ? C53 C51 H51 107.4 . . ? C50 C51 H51 107.4 . . ? S6 C51 H51 107.4 . . ? C54 C52 C49 113.5(2) . . ? C54 C52 S5 110.68(17) . . ? C49 C52 S5 106.44(16) . . ? C54 C52 H52 108.7 . . ? C49 C52 H52 108.7 . . ? S5 C52 H52 108.7 . . ? C54 C53 C51 109.7(2) . . ? C54 C53 H53A 109.7 . . ? C51 C53 H53A 109.7 . . ? C54 C53 H53B 109.7 . . ? C51 C53 H53B 109.7 . . ? H53A C53 H53B 108.2 . . ? C52 C54 C53 110.2(2) . . ? C52 C54 H54A 109.6 . . ? C53 C54 H54A 109.6 . . ? C52 C54 H54B 109.6 . . ? C53 C54 H54B 109.6 . . ? H54A C54 H54B 108.1 . . ? C4 S1 C40 102.07(12) . . ? C10 S2 C37 103.65(12) . . ? C16 S3 C44 101.38(12) . . ? C22 S4 C47 101.26(13) . . ? C28 S5 C52 103.79(11) . . ? C34 S6 C51 108.67(12) . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.465 _refine_diff_density_min -0.707 _refine_diff_density_rms 0.055