# Electronic Supplementary Material (ESI) for Chemical Science # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # 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_mh98 _audit_creation_method SHELXTL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C34 H28 S2' _chemical_formula_weight 500.68 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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' S S 0.3331 0.5567 '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 14.2992(6) _cell_length_b 7.0840(3) _cell_length_c 13.4824(6) _cell_angle_alpha 90.00 _cell_angle_beta 108.840(2) _cell_angle_gamma 90.00 _cell_volume 1292.54(10) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 7875 _cell_measurement_theta_min 6.54 _cell_measurement_theta_max 67.83 _exptl_crystal_description plate _exptl_crystal_colour red _exptl_crystal_size_max 0.17 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.286 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 528 _exptl_absorpt_coefficient_mu 2.014 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7258 _exptl_absorpt_correction_T_max 0.9421 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'Micro-focus I\mS 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 9736 _diffrn_reflns_av_R_equivalents 0.0680 _diffrn_reflns_av_sigmaI/netI 0.0344 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 6.54 _diffrn_reflns_theta_max 67.82 _reflns_number_total 2315 _reflns_number_gt 2161 _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^)+(0.0764P)^2^+0.4885P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2315 _refine_ls_number_parameters 219 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0418 _refine_ls_R_factor_gt 0.0398 _refine_ls_wR_factor_ref 0.1194 _refine_ls_wR_factor_gt 0.1170 _refine_ls_goodness_of_fit_ref 1.083 _refine_ls_restrained_S_all 1.083 _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 0.55952(3) 1.13866(6) 0.82925(3) 0.02279(18) Uani 1 1 d . . . C1 C 0.56162(12) 0.8896(2) 0.45495(13) 0.0182(3) Uani 1 1 d . . . C2 C 0.59078(11) 0.9278(2) 0.56494(13) 0.0179(3) Uani 1 1 d . . . C3 C 0.52605(11) 1.0398(2) 0.60749(12) 0.0174(3) Uani 1 1 d . . . C4 C 0.57674(11) 1.0455(2) 0.71974(13) 0.0191(4) Uani 1 1 d . . . C5 C 0.66476(11) 0.9454(2) 0.74341(13) 0.0190(4) Uani 1 1 d . . . C6 C 0.67444(12) 0.8732(2) 0.64572(13) 0.0189(4) Uani 1 1 d . . . C7 C 0.71872(12) 0.9466(2) 0.85192(13) 0.0219(4) Uani 1 1 d . . . C8 C 0.67121(13) 1.0450(2) 0.90739(14) 0.0242(4) Uani 1 1 d . . . C9 C 0.76275(11) 0.7713(2) 0.63893(12) 0.0197(4) Uani 1 1 d . . . C10 C 0.78719(12) 0.5922(2) 0.68622(13) 0.0232(4) Uani 1 1 d . . . C11 C 0.87530(13) 0.5071(3) 0.68625(14) 0.0271(4) Uani 1 1 d . . . C12 C 0.93843(13) 0.5909(3) 0.64038(14) 0.0293(4) Uani 1 1 d . . . C13 C 0.91200(12) 0.7655(3) 0.59220(13) 0.0270(4) Uani 1 1 d . . . C14 C 0.82545(12) 0.8576(2) 0.59077(13) 0.0219(4) Uani 1 1 d . . . C15 C 0.71763(15) 0.4892(3) 0.73151(17) 0.0299(4) Uani 1 1 d . . . C16 C 1.03410(16) 0.4968(4) 0.64381(18) 0.0410(6) Uani 1 1 d . . . C17 C 0.80421(14) 1.0509(3) 0.54248(16) 0.0291(4) Uani 1 1 d . . . H1 H 0.6048(14) 0.815(3) 0.4263(14) 0.018(4) Uiso 1 1 d . . . H7 H 0.7811(17) 0.884(3) 0.8833(18) 0.037(6) Uiso 1 1 d . . . H8 H 0.6868(17) 1.061(4) 0.976(2) 0.039(6) Uiso 1 1 d . . . H11 H 0.8937(17) 0.375(3) 0.7224(18) 0.034(6) Uiso 1 1 d . . . H13 H 0.9554(16) 0.839(3) 0.5568(16) 0.027(5) Uiso 1 1 d . . . H15A H 0.654(2) 0.478(4) 0.687(2) 0.059(8) Uiso 1 1 d . . . H15B H 0.7035(19) 0.557(4) 0.784(2) 0.054(7) Uiso 1 1 d . . . H15C H 0.743(2) 0.372(4) 0.758(2) 0.051(7) Uiso 1 1 d . . . H16A H 1.019(3) 0.348(6) 0.631(3) 0.108(14) Uiso 1 1 d . . . H16B H 1.055(3) 0.541(5) 0.594(3) 0.096(12) Uiso 1 1 d . . . H16C H 1.086(2) 0.519(5) 0.711(3) 0.083(10) Uiso 1 1 d . . . H17A H 0.751(2) 1.053(4) 0.476(2) 0.047(7) Uiso 1 1 d . . . H17B H 0.8613(17) 1.107(3) 0.5274(17) 0.032(6) Uiso 1 1 d . . . H17C H 0.7793(17) 1.124(3) 0.5858(19) 0.035(6) Uiso 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 S1 0.0237(3) 0.0231(3) 0.0203(3) -0.00281(14) 0.00530(19) 0.00283(15) C1 0.0163(8) 0.0172(7) 0.0208(8) 0.0004(6) 0.0058(6) 0.0006(6) C2 0.0149(7) 0.0165(8) 0.0222(8) 0.0005(6) 0.0056(6) 0.0002(6) C3 0.0165(8) 0.0160(8) 0.0202(8) -0.0005(6) 0.0064(6) -0.0004(6) C4 0.0172(8) 0.0160(8) 0.0234(8) -0.0012(6) 0.0054(6) 0.0006(6) C5 0.0150(7) 0.0172(8) 0.0228(8) 0.0014(6) 0.0033(6) -0.0014(6) C6 0.0160(8) 0.0175(8) 0.0217(8) 0.0008(6) 0.0039(6) -0.0008(6) C7 0.0177(8) 0.0214(8) 0.0241(9) 0.0025(7) 0.0031(7) -0.0028(7) C8 0.0265(9) 0.0222(9) 0.0199(9) -0.0015(7) 0.0018(7) -0.0037(7) C9 0.0141(7) 0.0219(8) 0.0196(8) -0.0022(6) 0.0006(6) 0.0023(6) C10 0.0202(8) 0.0231(8) 0.0215(8) -0.0008(7) 0.0001(7) 0.0036(7) C11 0.0236(9) 0.0283(10) 0.0238(9) -0.0021(7) 0.0001(7) 0.0095(7) C12 0.0199(9) 0.0406(10) 0.0216(9) -0.0060(8) -0.0011(7) 0.0116(8) C13 0.0183(8) 0.0397(10) 0.0213(9) -0.0034(8) 0.0043(7) 0.0021(7) C14 0.0170(8) 0.0275(9) 0.0177(8) -0.0026(6) 0.0008(6) 0.0003(6) C15 0.0310(10) 0.0243(10) 0.0344(10) 0.0068(8) 0.0106(9) 0.0049(8) C16 0.0259(10) 0.0628(16) 0.0322(11) 0.0021(10) 0.0064(9) 0.0218(10) C17 0.0246(9) 0.0306(10) 0.0325(10) 0.0040(8) 0.0098(8) -0.0006(8) _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 1.7061(16) . ? S1 C8 1.7362(18) . ? C1 C3 1.360(2) 3_676 ? C1 C2 1.431(2) . ? C1 H1 0.981(19) . ? C2 C6 1.388(2) . ? C2 C3 1.469(2) . ? C3 C1 1.360(2) 3_676 ? C3 C4 1.452(2) . ? C4 C5 1.389(2) . ? C5 C7 1.417(2) . ? C5 C6 1.460(2) . ? C6 C9 1.483(2) . ? C7 C8 1.355(3) . ? C7 H7 0.96(2) . ? C8 H8 0.88(2) . ? C9 C14 1.405(2) . ? C9 C10 1.412(2) . ? C10 C11 1.397(2) . ? C10 C15 1.512(3) . ? C11 C12 1.382(3) . ? C11 H11 1.05(2) . ? C12 C13 1.391(3) . ? C12 C16 1.509(2) . ? C13 C14 1.394(2) . ? C13 H13 1.03(2) . ? C14 C17 1.504(3) . ? C15 H15A 0.92(3) . ? C15 H15B 0.93(3) . ? C15 H15C 0.93(3) . ? C16 H16A 1.08(5) . ? C16 H16B 0.88(4) . ? C16 H16C 0.98(3) . ? C17 H17A 0.96(3) . ? C17 H17B 0.99(2) . ? C17 H17C 0.93(2) . ? 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 C8 90.90(8) . . ? C3 C1 C2 118.27(15) 3_676 . ? C3 C1 H1 121.7(11) 3_676 . ? C2 C1 H1 120.0(11) . . ? C6 C2 C1 130.50(15) . . ? C6 C2 C3 109.65(14) . . ? C1 C2 C3 119.84(15) . . ? C1 C3 C4 133.23(15) 3_676 . ? C1 C3 C2 121.88(15) 3_676 . ? C4 C3 C2 104.87(13) . . ? C5 C4 C3 109.60(14) . . ? C5 C4 S1 111.84(13) . . ? C3 C4 S1 138.56(12) . . ? C4 C5 C7 112.65(15) . . ? C4 C5 C6 108.32(14) . . ? C7 C5 C6 139.01(15) . . ? C2 C6 C5 107.54(14) . . ? C2 C6 C9 128.53(15) . . ? C5 C6 C9 123.82(14) . . ? C8 C7 C5 111.74(15) . . ? C8 C7 H7 123.6(14) . . ? C5 C7 H7 124.7(14) . . ? C7 C8 S1 112.87(13) . . ? C7 C8 H8 129.9(16) . . ? S1 C8 H8 117.1(15) . . ? C14 C9 C10 119.85(15) . . ? C14 C9 C6 119.98(15) . . ? C10 C9 C6 120.06(15) . . ? C11 C10 C9 118.66(17) . . ? C11 C10 C15 120.15(17) . . ? C9 C10 C15 121.12(15) . . ? C12 C11 C10 122.28(17) . . ? C12 C11 H11 119.3(12) . . ? C10 C11 H11 118.5(13) . . ? C11 C12 C13 118.18(16) . . ? C11 C12 C16 120.90(19) . . ? C13 C12 C16 120.92(19) . . ? C12 C13 C14 121.94(17) . . ? C12 C13 H13 123.1(12) . . ? C14 C13 H13 114.9(12) . . ? C13 C14 C9 119.06(16) . . ? C13 C14 C17 119.12(17) . . ? C9 C14 C17 121.75(15) . . ? C10 C15 H15A 114.8(17) . . ? C10 C15 H15B 113.0(17) . . ? H15A C15 H15B 98(2) . . ? C10 C15 H15C 111.0(17) . . ? H15A C15 H15C 111(2) . . ? H15B C15 H15C 109(2) . . ? C12 C16 H16A 107(2) . . ? C12 C16 H16B 111(2) . . ? H16A C16 H16B 109(3) . . ? C12 C16 H16C 111(2) . . ? H16A C16 H16C 111(3) . . ? H16B C16 H16C 108(3) . . ? C14 C17 H17A 113.6(16) . . ? C14 C17 H17B 113.1(13) . . ? H17A C17 H17B 104.8(19) . . ? C14 C17 H17C 107.3(14) . . ? H17A C17 H17C 103.3(19) . . ? H17B C17 H17C 114.5(19) . . ? 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 C3 C1 C2 C6 179.41(16) 3_676 . . . ? C3 C1 C2 C3 0.4(2) 3_676 . . . ? C6 C2 C3 C1 -179.62(14) . . . 3_676 ? C1 C2 C3 C1 -0.5(3) . . . 3_676 ? C6 C2 C3 C4 -0.77(17) . . . . ? C1 C2 C3 C4 178.40(14) . . . . ? C1 C3 C4 C5 178.62(17) 3_676 . . . ? C2 C3 C4 C5 -0.04(18) . . . . ? C1 C3 C4 S1 -1.5(3) 3_676 . . . ? C2 C3 C4 S1 179.85(15) . . . . ? C8 S1 C4 C5 0.44(13) . . . . ? C8 S1 C4 C3 -179.45(19) . . . . ? C3 C4 C5 C7 179.42(13) . . . . ? S1 C4 C5 C7 -0.50(18) . . . . ? C3 C4 C5 C6 0.79(18) . . . . ? S1 C4 C5 C6 -179.13(11) . . . . ? C1 C2 C6 C5 -177.80(16) . . . . ? C3 C2 C6 C5 1.25(18) . . . . ? C1 C2 C6 C9 5.9(3) . . . . ? C3 C2 C6 C9 -175.08(15) . . . . ? C4 C5 C6 C2 -1.27(18) . . . . ? C7 C5 C6 C2 -179.35(19) . . . . ? C4 C5 C6 C9 175.27(15) . . . . ? C7 C5 C6 C9 -2.8(3) . . . . ? C4 C5 C7 C8 0.3(2) . . . . ? C6 C5 C7 C8 178.31(19) . . . . ? C5 C7 C8 S1 0.05(19) . . . . ? C4 S1 C8 C7 -0.28(14) . . . . ? C2 C6 C9 C14 65.7(2) . . . . ? C5 C6 C9 C14 -110.04(18) . . . . ? C2 C6 C9 C10 -117.99(19) . . . . ? C5 C6 C9 C10 66.2(2) . . . . ? C14 C9 C10 C11 1.7(2) . . . . ? C6 C9 C10 C11 -174.57(15) . . . . ? C14 C9 C10 C15 -175.38(16) . . . . ? C6 C9 C10 C15 8.4(2) . . . . ? C9 C10 C11 C12 -0.9(3) . . . . ? C15 C10 C11 C12 176.16(17) . . . . ? C10 C11 C12 C13 -0.4(3) . . . . ? C10 C11 C12 C16 178.71(18) . . . . ? C11 C12 C13 C14 1.1(3) . . . . ? C16 C12 C13 C14 -178.06(17) . . . . ? C12 C13 C14 C9 -0.3(3) . . . . ? C12 C13 C14 C17 176.66(17) . . . . ? C10 C9 C14 C13 -1.1(2) . . . . ? C6 C9 C14 C13 175.19(15) . . . . ? C10 C9 C14 C17 -177.99(15) . . . . ? C6 C9 C14 C17 -1.7(2) . . . . ? _diffrn_measured_fraction_theta_max 0.981 _diffrn_reflns_theta_full 67.82 _diffrn_measured_fraction_theta_full 0.981 _refine_diff_density_max 0.391 _refine_diff_density_min -0.328 _refine_diff_density_rms 0.055 _database_code_depnum_ccdc_archive 'CCDC 949864' ####################################################################### # # 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_mh101 _audit_creation_method SHELXTL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C42 H32 S2' _chemical_formula_weight 600.80 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' 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 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 14.4327(5) _cell_length_b 11.8497(4) _cell_length_c 8.9975(3) _cell_angle_alpha 90.00 _cell_angle_beta 94.0200(10) _cell_angle_gamma 90.00 _cell_volume 1534.99(9) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 9934 _cell_measurement_theta_min 3.25 _cell_measurement_theta_max 35.13 _exptl_crystal_description block _exptl_crystal_colour dark _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.17 _exptl_crystal_size_min 0.09 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.300 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 632 _exptl_absorpt_coefficient_mu 0.204 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9603 _exptl_absorpt_correction_T_max 0.9819 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator 'Triumph mirror' _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 15512 _diffrn_reflns_av_R_equivalents 0.0358 _diffrn_reflns_av_sigmaI/netI 0.0283 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -7 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 3.25 _diffrn_reflns_theta_max 27.99 _reflns_number_total 3659 _reflns_number_gt 3222 _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^)+(0.0648P)^2^+2.0895P] 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 3659 _refine_ls_number_parameters 199 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0529 _refine_ls_R_factor_gt 0.0472 _refine_ls_wR_factor_ref 0.1350 _refine_ls_wR_factor_gt 0.1298 _refine_ls_goodness_of_fit_ref 1.039 _refine_ls_restrained_S_all 1.039 _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 0.79150(3) 0.45821(4) 0.84480(5) 0.01484(14) Uani 1 1 d . . . C1 C 0.54893(12) 0.54253(14) 0.3770(2) 0.0129(3) Uani 1 1 d . . . H1A H 0.5819 0.5698 0.2966 0.016 Uiso 1 1 calc R . . C2 C 0.59618(11) 0.51508(14) 0.5162(2) 0.0123(3) Uani 1 1 d . . . C3 C 0.54553(12) 0.47146(14) 0.63803(19) 0.0123(3) Uani 1 1 d . . . C4 C 0.61470(12) 0.45114(14) 0.7609(2) 0.0127(3) Uani 1 1 d . . . C5 C 0.70077(11) 0.48049(15) 0.7120(2) 0.0130(3) Uani 1 1 d . . . C6 C 0.69134(12) 0.52254(14) 0.5614(2) 0.0124(3) Uani 1 1 d . . . C7 C 0.61999(12) 0.40900(14) 0.9100(2) 0.0133(3) Uani 1 1 d . . . C8 C 0.71374(12) 0.40874(14) 0.9705(2) 0.0138(3) Uani 1 1 d . . . C9 C 0.73758(13) 0.36995(15) 1.1144(2) 0.0170(4) Uani 1 1 d . . . H9A H 0.8004 0.3708 1.1540 0.020 Uiso 1 1 calc R . . C10 C 0.66773(14) 0.33013(16) 1.1983(2) 0.0188(4) Uani 1 1 d . . . H10A H 0.6827 0.3035 1.2966 0.023 Uiso 1 1 calc R . . C11 C 0.57478(13) 0.32876(16) 1.1394(2) 0.0180(4) Uani 1 1 d . . . H11A H 0.5279 0.3003 1.1982 0.022 Uiso 1 1 calc R . . C12 C 0.55070(12) 0.36806(15) 0.9974(2) 0.0157(4) Uani 1 1 d . . . H12A H 0.4876 0.3674 0.9593 0.019 Uiso 1 1 calc R . . C13 C 0.76452(11) 0.56824(15) 0.47150(19) 0.0127(3) Uani 1 1 d . . . C14 C 0.83974(12) 0.50028(15) 0.4343(2) 0.0141(3) Uani 1 1 d . . . C15 C 0.90395(12) 0.54369(16) 0.3404(2) 0.0181(4) Uani 1 1 d . . . H15A H 0.9547 0.4979 0.3161 0.022 Uiso 1 1 calc R . . C16 C 0.89577(13) 0.65207(18) 0.2815(2) 0.0208(4) Uani 1 1 d . . . C17 C 0.82272(13) 0.71911(16) 0.3231(2) 0.0198(4) Uani 1 1 d . . . H17A H 0.8171 0.7939 0.2854 0.024 Uiso 1 1 calc R . . C18 C 0.75763(12) 0.68032(15) 0.4181(2) 0.0160(4) Uani 1 1 d . . . C19 C 0.85113(13) 0.38007(16) 0.4881(2) 0.0183(4) Uani 1 1 d . . . H19A H 0.9073 0.3476 0.4503 0.027 Uiso 1 1 calc R . . H19B H 0.7969 0.3356 0.4517 0.027 Uiso 1 1 calc R . . H19C H 0.8565 0.3790 0.5973 0.027 Uiso 1 1 calc R . . C20 C 0.96352(15) 0.6969(2) 0.1759(3) 0.0361(6) Uani 1 1 d . . . H20A H 1.0099 0.6388 0.1586 0.054 Uiso 1 1 calc R . . H20B H 0.9946 0.7639 0.2194 0.054 Uiso 1 1 calc R . . H20C H 0.9301 0.7171 0.0811 0.054 Uiso 1 1 calc R . . C21 C 0.68429(13) 0.76179(16) 0.4645(2) 0.0209(4) Uani 1 1 d . . . H21A H 0.6918 0.8345 0.4149 0.031 Uiso 1 1 calc R . . H21B H 0.6910 0.7724 0.5727 0.031 Uiso 1 1 calc R . . H21C H 0.6225 0.7312 0.4359 0.031 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 0.0101(2) 0.0171(2) 0.0170(2) 0.00127(15) -0.00090(15) 0.00010(15) C1 0.0113(8) 0.0129(8) 0.0149(8) 0.0013(6) 0.0032(6) 0.0002(6) C2 0.0103(7) 0.0117(7) 0.0151(8) 0.0005(6) 0.0016(6) 0.0000(6) C3 0.0120(8) 0.0119(8) 0.0130(8) 0.0006(6) 0.0013(6) 0.0000(6) C4 0.0117(8) 0.0116(8) 0.0149(8) -0.0001(6) 0.0019(6) 0.0003(6) C5 0.0097(7) 0.0136(8) 0.0157(8) 0.0001(6) -0.0002(6) 0.0006(6) C6 0.0107(7) 0.0107(7) 0.0160(8) -0.0002(6) 0.0013(6) 0.0004(6) C7 0.0144(8) 0.0102(7) 0.0148(8) -0.0018(6) -0.0015(6) 0.0014(6) C8 0.0142(8) 0.0110(8) 0.0162(8) -0.0013(6) 0.0015(6) 0.0004(6) C9 0.0186(8) 0.0146(8) 0.0171(9) -0.0011(7) -0.0036(7) 0.0011(7) C10 0.0245(9) 0.0162(9) 0.0153(9) 0.0014(7) -0.0015(7) 0.0002(7) C11 0.0218(9) 0.0154(8) 0.0172(9) 0.0011(7) 0.0037(7) -0.0027(7) C12 0.0147(8) 0.0146(8) 0.0178(9) 0.0000(6) 0.0013(6) -0.0006(6) C13 0.0085(7) 0.0146(8) 0.0151(8) 0.0011(6) 0.0007(6) -0.0013(6) C14 0.0108(7) 0.0163(8) 0.0152(8) 0.0009(6) 0.0000(6) 0.0002(6) C15 0.0104(8) 0.0225(9) 0.0215(9) 0.0022(7) 0.0031(7) 0.0021(7) C16 0.0127(8) 0.0266(10) 0.0232(10) 0.0082(8) 0.0030(7) -0.0014(7) C17 0.0145(8) 0.0184(9) 0.0266(10) 0.0080(7) 0.0012(7) -0.0018(7) C18 0.0113(8) 0.0157(8) 0.0209(9) 0.0019(7) 0.0002(6) -0.0007(6) C19 0.0166(8) 0.0170(9) 0.0214(9) 0.0022(7) 0.0020(7) 0.0027(7) C20 0.0203(10) 0.0461(14) 0.0436(14) 0.0265(11) 0.0141(9) 0.0041(9) C21 0.0181(9) 0.0147(8) 0.0302(11) 0.0019(7) 0.0045(7) 0.0022(7) _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 C5 1.7301(18) . ? S1 C8 1.7491(18) . ? C1 C3 1.371(2) 3_666 ? C1 C2 1.421(2) . ? C1 H1A 0.9500 . ? C2 C6 1.407(2) . ? C2 C3 1.454(2) . ? C3 C1 1.371(2) 3_666 ? C3 C4 1.457(2) . ? C4 C5 1.391(2) . ? C4 C7 1.429(2) . ? C5 C6 1.441(2) . ? C6 C13 1.477(2) . ? C7 C12 1.401(2) . ? C7 C8 1.423(2) . ? C8 C9 1.394(3) . ? C9 C10 1.384(3) . ? C9 H9A 0.9500 . ? C10 C11 1.407(3) . ? C10 H10A 0.9500 . ? C11 C12 1.381(3) . ? C11 H11A 0.9500 . ? C12 H12A 0.9500 . ? C13 C14 1.411(2) . ? C13 C18 1.414(2) . ? C14 C15 1.395(2) . ? C14 C19 1.510(3) . ? C15 C16 1.391(3) . ? C15 H15A 0.9500 . ? C16 C17 1.392(3) . ? C16 C20 1.507(3) . ? C17 C18 1.392(3) . ? C17 H17A 0.9500 . ? C18 C21 1.513(3) . ? 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 . ? 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 C5 S1 C8 90.50(8) . . ? C3 C1 C2 118.13(16) 3_666 . ? C3 C1 H1A 120.9 3_666 . ? C2 C1 H1A 120.9 . . ? C6 C2 C1 129.66(16) . . ? C6 C2 C3 109.67(15) . . ? C1 C2 C3 120.67(15) . . ? C1 C3 C2 121.19(16) 3_666 . ? C1 C3 C4 132.75(16) 3_666 . ? C2 C3 C4 106.06(14) . . ? C5 C4 C7 113.24(15) . . ? C5 C4 C3 107.36(15) . . ? C7 C4 C3 139.38(16) . . ? C4 C5 C6 110.87(15) . . ? C4 C5 S1 113.13(13) . . ? C6 C5 S1 135.99(13) . . ? C2 C6 C5 106.01(15) . . ? C2 C6 C13 125.84(16) . . ? C5 C6 C13 128.12(15) . . ? C12 C7 C8 118.79(16) . . ? C12 C7 C4 130.91(16) . . ? C8 C7 C4 110.28(15) . . ? C9 C8 C7 121.46(16) . . ? C9 C8 S1 125.67(14) . . ? C7 C8 S1 112.85(13) . . ? C10 C9 C8 118.51(17) . . ? C10 C9 H9A 120.7 . . ? C8 C9 H9A 120.7 . . ? C9 C10 C11 120.66(17) . . ? C9 C10 H10A 119.7 . . ? C11 C10 H10A 119.7 . . ? C12 C11 C10 121.05(17) . . ? C12 C11 H11A 119.5 . . ? C10 C11 H11A 119.5 . . ? C11 C12 C7 119.51(17) . . ? C11 C12 H12A 120.2 . . ? C7 C12 H12A 120.2 . . ? C14 C13 C18 119.51(16) . . ? C14 C13 C6 120.81(16) . . ? C18 C13 C6 119.65(15) . . ? C15 C14 C13 119.21(16) . . ? C15 C14 C19 118.69(16) . . ? C13 C14 C19 122.06(16) . . ? C16 C15 C14 121.94(17) . . ? C16 C15 H15A 119.0 . . ? C14 C15 H15A 119.0 . . ? C15 C16 C17 118.01(17) . . ? C15 C16 C20 121.61(18) . . ? C17 C16 C20 120.37(19) . . ? C18 C17 C16 122.22(17) . . ? C18 C17 H17A 118.9 . . ? C16 C17 H17A 118.9 . . ? C17 C18 C13 119.00(17) . . ? C17 C18 C21 118.31(17) . . ? C13 C18 C21 122.65(16) . . ? C14 C19 H19A 109.5 . . ? C14 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C14 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 . . ? 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 . . ? 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 C3 C1 C2 C6 -179.29(17) 3_666 . . . ? C3 C1 C2 C3 1.1(3) 3_666 . . . ? C6 C2 C3 C1 179.18(16) . . . 3_666 ? C1 C2 C3 C1 -1.1(3) . . . 3_666 ? C6 C2 C3 C4 -0.57(19) . . . . ? C1 C2 C3 C4 179.12(15) . . . . ? C1 C3 C4 C5 179.76(19) 3_666 . . . ? C2 C3 C4 C5 -0.53(19) . . . . ? C1 C3 C4 C7 1.6(4) 3_666 . . . ? C2 C3 C4 C7 -178.6(2) . . . . ? C7 C4 C5 C6 -179.90(14) . . . . ? C3 C4 C5 C6 1.4(2) . . . . ? C7 C4 C5 S1 0.0(2) . . . . ? C3 C4 C5 S1 -178.68(12) . . . . ? C8 S1 C5 C4 -0.20(14) . . . . ? C8 S1 C5 C6 179.64(19) . . . . ? C1 C2 C6 C5 -178.25(17) . . . . ? C3 C2 C6 C5 1.40(19) . . . . ? C1 C2 C6 C13 3.6(3) . . . . ? C3 C2 C6 C13 -176.78(16) . . . . ? C4 C5 C6 C2 -1.8(2) . . . . ? S1 C5 C6 C2 178.38(16) . . . . ? C4 C5 C6 C13 176.34(16) . . . . ? S1 C5 C6 C13 -3.5(3) . . . . ? C5 C4 C7 C12 -177.95(18) . . . . ? C3 C4 C7 C12 0.1(4) . . . . ? C5 C4 C7 C8 0.3(2) . . . . ? C3 C4 C7 C8 178.3(2) . . . . ? C12 C7 C8 C9 -0.7(3) . . . . ? C4 C7 C8 C9 -179.17(16) . . . . ? C12 C7 C8 S1 178.04(13) . . . . ? C4 C7 C8 S1 -0.44(19) . . . . ? C5 S1 C8 C9 179.04(17) . . . . ? C5 S1 C8 C7 0.37(14) . . . . ? C7 C8 C9 C10 0.6(3) . . . . ? S1 C8 C9 C10 -177.95(14) . . . . ? C8 C9 C10 C11 0.1(3) . . . . ? C9 C10 C11 C12 -0.7(3) . . . . ? C10 C11 C12 C7 0.6(3) . . . . ? C8 C7 C12 C11 0.1(3) . . . . ? C4 C7 C12 C11 178.19(18) . . . . ? C2 C6 C13 C14 -119.9(2) . . . . ? C5 C6 C13 C14 62.3(3) . . . . ? C2 C6 C13 C18 58.0(3) . . . . ? C5 C6 C13 C18 -119.7(2) . . . . ? C18 C13 C14 C15 -2.6(3) . . . . ? C6 C13 C14 C15 175.43(17) . . . . ? C18 C13 C14 C19 179.87(17) . . . . ? C6 C13 C14 C19 -2.1(3) . . . . ? C13 C14 C15 C16 -0.4(3) . . . . ? C19 C14 C15 C16 177.28(18) . . . . ? C14 C15 C16 C17 2.3(3) . . . . ? C14 C15 C16 C20 -177.8(2) . . . . ? C15 C16 C17 C18 -1.4(3) . . . . ? C20 C16 C17 C18 178.8(2) . . . . ? C16 C17 C18 C13 -1.5(3) . . . . ? C16 C17 C18 C21 176.24(19) . . . . ? C14 C13 C18 C17 3.5(3) . . . . ? C6 C13 C18 C17 -174.56(17) . . . . ? C14 C13 C18 C21 -174.18(17) . . . . ? C6 C13 C18 C21 7.8(3) . . . . ? _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 27.99 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 0.538 _refine_diff_density_min -0.568 _refine_diff_density_rms 0.071 _database_code_depnum_ccdc_archive 'CCDC 949865' ####################################################################### # # 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_mo_mh100_0m _audit_creation_method SHELXTL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C42 H32 S2' _chemical_formula_weight 600.80 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' 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 P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 13.689(2) _cell_length_b 7.3177(12) _cell_length_c 17.167(3) _cell_angle_alpha 90.00 _cell_angle_beta 112.808(3) _cell_angle_gamma 90.00 _cell_volume 1585.2(4) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 4282 _cell_measurement_theta_min 2.42 _cell_measurement_theta_max 28.04 _exptl_crystal_description plate _exptl_crystal_colour red _exptl_crystal_size_max 0.19 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.259 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 632 _exptl_absorpt_coefficient_mu 0.198 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9634 _exptl_absorpt_correction_T_max 0.9941 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator 'Triumph mirror' _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 10867 _diffrn_reflns_av_R_equivalents 0.0518 _diffrn_reflns_av_sigmaI/netI 0.0516 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.42 _diffrn_reflns_theta_max 27.00 _reflns_number_total 3372 _reflns_number_gt 2528 _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, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0682P)^2^+0.3110P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3372 _refine_ls_number_parameters 263 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0730 _refine_ls_R_factor_gt 0.0483 _refine_ls_wR_factor_ref 0.1261 _refine_ls_wR_factor_gt 0.1135 _refine_ls_goodness_of_fit_ref 1.047 _refine_ls_restrained_S_all 1.047 _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 0.75574(4) -0.19446(7) 0.76867(3) 0.01750(16) Uani 1 1 d . . . C1 C 0.98656(17) 0.1157(3) 1.06359(14) 0.0155(4) Uani 1 1 d . . . C2 C 0.89914(17) 0.0602(3) 0.99101(14) 0.0157(4) Uani 1 1 d . . . C3 C 0.91434(17) -0.0563(3) 0.92778(13) 0.0156(4) Uani 1 1 d . . . C4 C 0.81018(17) -0.0813(3) 0.86354(14) 0.0160(4) Uani 1 1 d . . . C5 C 0.73632(17) 0.0142(3) 0.88517(14) 0.0165(4) Uani 1 1 d . . . C6 C 0.79056(17) 0.1013(3) 0.96530(14) 0.0160(4) Uani 1 1 d . . . C7 C 0.63067(17) 0.0015(3) 0.82111(14) 0.0157(4) Uani 1 1 d . . . C8 C 0.62983(17) -0.1071(3) 0.75249(14) 0.0170(5) Uani 1 1 d . . . C9 C 0.53870(18) -0.1319(3) 0.68027(15) 0.0213(5) Uani 1 1 d . . . C10 C 0.44660(19) -0.0454(3) 0.67568(17) 0.0245(5) Uani 1 1 d . . . C11 C 0.44515(18) 0.0607(3) 0.74280(16) 0.0229(5) Uani 1 1 d . . . C12 C 0.53499(17) 0.0836(3) 0.81506(15) 0.0197(5) Uani 1 1 d . . . C13 C 0.74019(16) 0.1997(3) 1.01577(14) 0.0165(4) Uani 1 1 d . . . C14 C 0.70132(17) 0.3781(3) 0.99417(14) 0.0185(5) Uani 1 1 d . . . C15 C 0.64996(17) 0.4617(3) 1.04127(15) 0.0214(5) Uani 1 1 d . . . C16 C 0.63692(17) 0.3741(3) 1.10792(15) 0.0223(5) Uani 1 1 d . . . C17 C 0.67688(18) 0.1981(3) 1.12870(15) 0.0218(5) Uani 1 1 d . . . C18 C 0.72825(17) 0.1095(3) 1.08350(14) 0.0193(5) Uani 1 1 d . . . C19 C 0.7164(2) 0.4807(3) 0.92390(18) 0.0271(6) Uani 1 1 d . . . C20 C 0.5821(2) 0.4668(4) 1.15856(18) 0.0311(6) Uani 1 1 d . . . C21 C 0.7699(2) -0.0819(3) 1.10805(18) 0.0293(6) Uani 1 1 d . . . H1 H 0.9807(18) 0.186(3) 1.1080(16) 0.016(6) Uiso 1 1 d . . . H9 H 0.538(2) -0.202(3) 0.6342(17) 0.023(6) Uiso 1 1 d . . . H10 H 0.385(2) -0.060(3) 0.6284(17) 0.022(6) Uiso 1 1 d . . . H11 H 0.377(2) 0.121(4) 0.7403(17) 0.029(7) Uiso 1 1 d . . . H12 H 0.5349(19) 0.155(3) 0.8626(16) 0.020(6) Uiso 1 1 d . . . H15 H 0.619(2) 0.584(4) 1.0247(18) 0.034(7) Uiso 1 1 d . . . H17 H 0.6660(19) 0.134(3) 1.1757(16) 0.019(6) Uiso 1 1 d . . . H19A H 0.679(2) 0.424(4) 0.869(2) 0.047(9) Uiso 1 1 d . . . H19B H 0.692(2) 0.607(5) 0.9227(19) 0.044(8) Uiso 1 1 d . . . H19C H 0.793(2) 0.487(3) 0.9342(16) 0.027(7) Uiso 1 1 d . . . H20A H 0.634(3) 0.553(5) 1.203(3) 0.068(11) Uiso 1 1 d . . . H20B H 0.522(3) 0.538(4) 1.122(2) 0.055(9) Uiso 1 1 d . . . H20C H 0.559(2) 0.375(5) 1.192(2) 0.052(9) Uiso 1 1 d . . . H21A H 0.848(2) -0.080(4) 1.1410(18) 0.036(8) Uiso 1 1 d . . . H21B H 0.742(2) -0.143(4) 1.1503(18) 0.036(7) Uiso 1 1 d . . . H21C H 0.749(2) -0.159(4) 1.057(2) 0.046(9) Uiso 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 S1 0.0189(3) 0.0161(3) 0.0135(3) -0.0025(2) 0.0018(2) 0.0012(2) C1 0.0187(10) 0.0135(10) 0.0122(11) 0.0011(8) 0.0037(9) 0.0025(8) C2 0.0175(10) 0.0130(10) 0.0157(12) 0.0005(8) 0.0054(9) 0.0013(8) C3 0.0201(11) 0.0123(10) 0.0132(12) 0.0001(8) 0.0052(9) 0.0016(8) C4 0.0206(11) 0.0120(10) 0.0134(11) 0.0009(8) 0.0043(9) 0.0008(8) C5 0.0191(10) 0.0132(10) 0.0158(12) 0.0017(8) 0.0053(9) 0.0004(8) C6 0.0181(10) 0.0118(10) 0.0151(12) 0.0025(8) 0.0031(9) 0.0013(8) C7 0.0184(10) 0.0107(9) 0.0155(12) 0.0026(8) 0.0039(9) -0.0015(8) C8 0.0189(10) 0.0125(10) 0.0171(12) 0.0027(8) 0.0041(9) -0.0009(8) C9 0.0218(11) 0.0170(11) 0.0178(13) -0.0011(9) -0.0003(10) -0.0043(9) C10 0.0193(11) 0.0198(12) 0.0259(15) 0.0030(9) -0.0006(11) -0.0050(9) C11 0.0174(11) 0.0182(11) 0.0279(14) 0.0038(9) 0.0030(10) -0.0004(9) C12 0.0194(11) 0.0154(11) 0.0224(13) 0.0017(9) 0.0059(10) 0.0017(8) C13 0.0130(9) 0.0179(10) 0.0155(12) -0.0031(8) 0.0020(9) 0.0001(8) C14 0.0157(10) 0.0181(11) 0.0172(12) -0.0014(9) 0.0015(9) 0.0002(8) C15 0.0187(11) 0.0199(12) 0.0204(13) -0.0023(9) 0.0019(10) 0.0057(9) C16 0.0159(10) 0.0287(12) 0.0187(13) -0.0070(9) 0.0028(10) 0.0022(9) C17 0.0201(11) 0.0251(12) 0.0170(12) 0.0002(9) 0.0038(10) -0.0013(9) C18 0.0182(10) 0.0192(11) 0.0177(12) -0.0009(9) 0.0039(9) 0.0003(9) C19 0.0364(14) 0.0195(13) 0.0294(16) 0.0037(10) 0.0171(13) 0.0064(10) C20 0.0307(14) 0.0388(16) 0.0234(15) -0.0040(12) 0.0101(13) 0.0117(12) C21 0.0407(16) 0.0228(13) 0.0256(15) 0.0043(11) 0.0141(13) 0.0052(11) _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(2) . ? S1 C8 1.756(2) . ? C1 C3 1.377(3) 3_757 ? C1 C2 1.412(3) . ? C1 H1 0.95(2) . ? C2 C6 1.409(3) . ? C2 C3 1.457(3) . ? C3 C1 1.377(3) 3_757 ? C3 C4 1.437(3) . ? C4 C5 1.393(3) . ? C5 C6 1.435(3) . ? C5 C7 1.441(3) . ? C6 C13 1.486(3) . ? C7 C12 1.408(3) . ? C7 C8 1.418(3) . ? C8 C9 1.388(3) . ? C9 C10 1.385(3) . ? C9 H9 0.94(3) . ? C10 C11 1.396(3) . ? C10 H10 0.93(3) . ? C11 C12 1.377(3) . ? C11 H11 1.02(3) . ? C12 H12 0.97(2) . ? C13 C18 1.401(3) . ? C13 C14 1.404(3) . ? C14 C15 1.401(3) . ? C14 C19 1.501(3) . ? C15 C16 1.382(3) . ? C15 H15 0.98(3) . ? C16 C17 1.390(3) . ? C16 C20 1.511(3) . ? C17 C18 1.393(3) . ? C17 H17 0.99(2) . ? C18 C21 1.509(3) . ? C19 H19A 0.97(3) . ? C19 H19B 0.98(3) . ? C19 H19C 0.99(3) . ? C20 H20A 1.03(4) . ? C20 H20B 0.97(4) . ? C20 H20C 1.01(3) . ? C21 H21A 1.00(3) . ? C21 H21B 1.05(3) . ? C21 H21C 0.99(3) . ? 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 C8 90.75(10) . . ? C3 C1 C2 117.8(2) 3_757 . ? C3 C1 H1 118.1(15) 3_757 . ? C2 C1 H1 124.0(14) . . ? C1 C2 C6 130.2(2) . . ? C1 C2 C3 120.59(19) . . ? C6 C2 C3 109.23(19) . . ? C1 C3 C4 133.3(2) 3_757 . ? C1 C3 C2 121.6(2) 3_757 . ? C4 C3 C2 105.11(18) . . ? C5 C4 C3 109.78(19) . . ? C5 C4 S1 113.67(16) . . ? C3 C4 S1 136.54(16) . . ? C4 C5 C6 108.61(19) . . ? C4 C5 C7 112.45(19) . . ? C6 C5 C7 138.90(19) . . ? C2 C6 C5 107.25(18) . . ? C2 C6 C13 126.3(2) . . ? C5 C6 C13 126.14(19) . . ? C12 C7 C8 118.1(2) . . ? C12 C7 C5 131.2(2) . . ? C8 C7 C5 110.65(18) . . ? C9 C8 C7 122.0(2) . . ? C9 C8 S1 125.50(18) . . ? C7 C8 S1 112.41(16) . . ? C10 C9 C8 118.3(2) . . ? C10 C9 H9 119.3(16) . . ? C8 C9 H9 122.4(16) . . ? C9 C10 C11 120.7(2) . . ? C9 C10 H10 120.2(15) . . ? C11 C10 H10 119.0(15) . . ? C12 C11 C10 121.2(2) . . ? C12 C11 H11 118.0(15) . . ? C10 C11 H11 120.8(15) . . ? C11 C12 C7 119.7(2) . . ? C11 C12 H12 122.1(15) . . ? C7 C12 H12 118.2(15) . . ? C18 C13 C14 120.22(19) . . ? C18 C13 C6 119.02(19) . . ? C14 C13 C6 120.72(19) . . ? C15 C14 C13 118.5(2) . . ? C15 C14 C19 120.1(2) . . ? C13 C14 C19 121.41(19) . . ? C16 C15 C14 122.0(2) . . ? C16 C15 H15 118.9(15) . . ? C14 C15 H15 119.1(15) . . ? C15 C16 C17 118.5(2) . . ? C15 C16 C20 121.3(2) . . ? C17 C16 C20 120.1(2) . . ? C16 C17 C18 121.4(2) . . ? C16 C17 H17 118.4(14) . . ? C18 C17 H17 120.2(14) . . ? C17 C18 C13 119.3(2) . . ? C17 C18 C21 119.6(2) . . ? C13 C18 C21 121.1(2) . . ? C14 C19 H19A 112.4(18) . . ? C14 C19 H19B 109.5(17) . . ? H19A C19 H19B 110(3) . . ? C14 C19 H19C 110.2(15) . . ? H19A C19 H19C 108(2) . . ? H19B C19 H19C 107(2) . . ? C16 C20 H20A 109.9(19) . . ? C16 C20 H20B 110.9(19) . . ? H20A C20 H20B 108(3) . . ? C16 C20 H20C 111.4(18) . . ? H20A C20 H20C 106(3) . . ? H20B C20 H20C 110(3) . . ? C18 C21 H21A 110.6(16) . . ? C18 C21 H21B 112.9(15) . . ? H21A C21 H21B 103(2) . . ? C18 C21 H21C 109.6(18) . . ? H21A C21 H21C 113(2) . . ? H21B C21 H21C 108(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 C3 C1 C2 C6 -179.1(2) 3_757 . . . ? C3 C1 C2 C3 0.0(3) 3_757 . . . ? C1 C2 C3 C1 0.0(3) . . . 3_757 ? C6 C2 C3 C1 179.23(19) . . . 3_757 ? C1 C2 C3 C4 -178.99(19) . . . . ? C6 C2 C3 C4 0.3(2) . . . . ? C1 C3 C4 C5 -178.2(2) 3_757 . . . ? C2 C3 C4 C5 0.6(2) . . . . ? C1 C3 C4 S1 0.8(4) 3_757 . . . ? C2 C3 C4 S1 179.60(18) . . . . ? C8 S1 C4 C5 2.38(17) . . . . ? C8 S1 C4 C3 -176.6(2) . . . . ? C3 C4 C5 C6 -1.2(2) . . . . ? S1 C4 C5 C6 179.56(14) . . . . ? C3 C4 C5 C7 177.22(17) . . . . ? S1 C4 C5 C7 -2.0(2) . . . . ? C1 C2 C6 C5 178.2(2) . . . . ? C3 C2 C6 C5 -0.9(2) . . . . ? C1 C2 C6 C13 -7.7(4) . . . . ? C3 C2 C6 C13 173.20(19) . . . . ? C4 C5 C6 C2 1.3(2) . . . . ? C7 C5 C6 C2 -176.4(2) . . . . ? C4 C5 C6 C13 -172.85(19) . . . . ? C7 C5 C6 C13 9.4(4) . . . . ? C4 C5 C7 C12 -176.1(2) . . . . ? C6 C5 C7 C12 1.5(4) . . . . ? C4 C5 C7 C8 0.4(2) . . . . ? C6 C5 C7 C8 178.1(2) . . . . ? C12 C7 C8 C9 0.9(3) . . . . ? C5 C7 C8 C9 -176.17(19) . . . . ? C12 C7 C8 S1 178.41(15) . . . . ? C5 C7 C8 S1 1.4(2) . . . . ? C4 S1 C8 C9 175.3(2) . . . . ? C4 S1 C8 C7 -2.13(16) . . . . ? C7 C8 C9 C10 0.7(3) . . . . ? S1 C8 C9 C10 -176.54(17) . . . . ? C8 C9 C10 C11 -1.3(3) . . . . ? C9 C10 C11 C12 0.5(3) . . . . ? C10 C11 C12 C7 1.1(3) . . . . ? C8 C7 C12 C11 -1.8(3) . . . . ? C5 C7 C12 C11 174.6(2) . . . . ? C2 C6 C13 C18 -73.5(3) . . . . ? C5 C6 C13 C18 99.5(3) . . . . ? C2 C6 C13 C14 108.9(3) . . . . ? C5 C6 C13 C14 -78.0(3) . . . . ? C18 C13 C14 C15 -0.6(3) . . . . ? C6 C13 C14 C15 177.0(2) . . . . ? C18 C13 C14 C19 177.8(2) . . . . ? C6 C13 C14 C19 -4.7(3) . . . . ? C13 C14 C15 C16 0.1(3) . . . . ? C19 C14 C15 C16 -178.2(2) . . . . ? C14 C15 C16 C17 0.4(4) . . . . ? C14 C15 C16 C20 179.5(2) . . . . ? C15 C16 C17 C18 -0.6(3) . . . . ? C20 C16 C17 C18 -179.7(2) . . . . ? C16 C17 C18 C13 0.2(3) . . . . ? C16 C17 C18 C21 -179.7(2) . . . . ? C14 C13 C18 C17 0.4(3) . . . . ? C6 C13 C18 C17 -177.2(2) . . . . ? C14 C13 C18 C21 -179.7(2) . . . . ? C6 C13 C18 C21 2.7(3) . . . . ? _diffrn_measured_fraction_theta_max 0.976 _diffrn_reflns_theta_full 27.00 _diffrn_measured_fraction_theta_full 0.976 _refine_diff_density_max 0.485 _refine_diff_density_min -0.265 _refine_diff_density_rms 0.063 _database_code_depnum_ccdc_archive 'CCDC 949866' ####################################################################### # # 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_mo_mh114_0m _audit_creation_method SHELXTL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C17 H14 S' _chemical_formula_weight 250.34 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' 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 7.9092(14) _cell_length_b 8.0857(14) _cell_length_c 10.8326(19) _cell_angle_alpha 91.725(4) _cell_angle_beta 107.227(4) _cell_angle_gamma 105.087(4) _cell_volume 634.54(19) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 5053 _cell_measurement_theta_min 2.63 _cell_measurement_theta_max 28.28 _exptl_crystal_description plate _exptl_crystal_colour black _exptl_crystal_size_max 0.14 _exptl_crystal_size_mid 0.04 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.310 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 264 _exptl_absorpt_coefficient_mu 0.232 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9682 _exptl_absorpt_correction_T_max 0.9954 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator 'triumph mirror' _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 8463 _diffrn_reflns_av_R_equivalents 0.0304 _diffrn_reflns_av_sigmaI/netI 0.0310 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 1.98 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2237 _reflns_number_gt 1893 _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^)+(0.0604P)^2^+0.7934P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2237 _refine_ls_number_parameters 219 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0549 _refine_ls_R_factor_gt 0.0449 _refine_ls_wR_factor_ref 0.1196 _refine_ls_wR_factor_gt 0.1126 _refine_ls_goodness_of_fit_ref 1.005 _refine_ls_restrained_S_all 1.005 _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 0.84680(8) 0.42922(8) 0.26869(6) 0.0208(2) Uani 1 1 d . . . C1 C 0.5018(3) -0.1496(3) 0.4253(2) 0.0132(5) Uani 1 1 d . . . C2 C 0.5847(3) 0.0197(3) 0.4029(2) 0.0135(5) Uani 1 1 d . . . C3 C 0.5813(3) 0.1686(3) 0.4802(2) 0.0127(5) Uani 1 1 d . . . C4 C 0.6780(3) 0.3204(3) 0.4330(2) 0.0154(5) Uani 1 1 d . . . C5 C 0.7349(3) 0.2613(3) 0.3352(2) 0.0153(5) Uani 1 1 d . . . C6 C 0.6778(3) 0.0749(3) 0.3136(2) 0.0141(5) Uani 1 1 d . . . C7 C 0.7257(3) 0.5038(3) 0.4537(2) 0.0124(5) Uani 1 1 d . . . C8 C 0.8174(4) 0.5762(3) 0.3721(3) 0.0231(6) Uani 1 1 d . . . C9 C 0.7064(3) -0.0356(3) 0.2149(2) 0.0140(5) Uani 1 1 d . . . C10 C 0.8864(3) -0.0335(3) 0.2180(2) 0.0160(5) Uani 1 1 d . . . C11 C 0.9085(3) -0.1386(3) 0.1232(2) 0.0179(5) Uani 1 1 d . . . C12 C 0.7611(3) -0.2465(3) 0.0275(2) 0.0194(5) Uani 1 1 d . . . C13 C 0.5844(3) -0.2490(3) 0.0266(2) 0.0167(5) Uani 1 1 d . . . C14 C 0.5544(3) -0.1443(3) 0.1176(2) 0.0149(5) Uani 1 1 d . . . C15 C 1.0538(4) 0.0714(4) 0.3245(3) 0.0216(6) Uani 1 1 d . . . C16 C 0.7903(5) -0.3590(4) -0.0734(3) 0.0308(7) Uani 1 1 d . . . C17 C 0.3597(3) -0.1477(3) 0.1060(2) 0.0176(5) Uani 1 1 d . . . H1 H 0.499(3) -0.245(3) 0.375(2) 0.017(6) Uiso 1 1 d . . . H7 H 0.701(3) 0.548(3) 0.500(2) 0.008(7) Uiso 1 1 d . . . H8 H 0.861(4) 0.687(4) 0.367(3) 0.030(8) Uiso 1 1 d . . . H11 H 1.025(4) -0.136(3) 0.127(2) 0.017(6) Uiso 1 1 d . . . H13 H 0.481(4) -0.324(3) -0.041(3) 0.017(6) Uiso 1 1 d . . . H15A H 1.040(5) 0.062(5) 0.403(4) 0.062(12) Uiso 1 1 d . . . H15B H 1.156(5) 0.045(4) 0.326(3) 0.051(10) Uiso 1 1 d . . . H15C H 1.067(5) 0.182(5) 0.324(3) 0.054(11) Uiso 1 1 d . . . H16A H 0.835(6) -0.449(6) -0.040(4) 0.077(13) Uiso 1 1 d . . . H16B H 0.880(5) -0.310(5) -0.096(4) 0.055(11) Uiso 1 1 d . . . H16C H 0.682(4) -0.392(4) -0.155(3) 0.037(8) Uiso 1 1 d . . . H17A H 0.288(4) -0.176(4) 0.020(3) 0.031(8) Uiso 1 1 d . . . H17B H 0.353(4) -0.037(4) 0.134(3) 0.026(7) Uiso 1 1 d . . . H17C H 0.308(4) -0.229(4) 0.156(3) 0.026(7) Uiso 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 S1 0.0224(4) 0.0195(3) 0.0191(3) 0.0043(2) 0.0075(3) 0.0023(2) C1 0.0127(11) 0.0141(11) 0.0121(11) -0.0014(9) 0.0022(9) 0.0049(9) C2 0.0118(11) 0.0174(11) 0.0113(11) 0.0018(9) 0.0029(9) 0.0049(9) C3 0.0115(11) 0.0126(11) 0.0129(11) 0.0014(9) 0.0019(9) 0.0040(9) C4 0.0139(11) 0.0178(12) 0.0137(11) 0.0011(9) 0.0032(9) 0.0046(9) C5 0.0125(11) 0.0164(12) 0.0146(11) 0.0039(9) 0.0030(9) 0.0012(9) C6 0.0103(11) 0.0171(11) 0.0135(11) 0.0025(9) 0.0020(9) 0.0036(9) C7 0.0135(12) 0.0151(12) 0.0115(12) 0.0016(9) 0.0063(10) 0.0063(9) C8 0.0236(13) 0.0133(13) 0.0273(14) 0.0046(10) 0.0044(11) 0.0005(10) C9 0.0151(12) 0.0156(11) 0.0129(11) 0.0051(9) 0.0057(9) 0.0052(9) C10 0.0152(12) 0.0173(11) 0.0166(12) 0.0067(9) 0.0063(10) 0.0046(9) C11 0.0149(12) 0.0228(13) 0.0233(13) 0.0091(10) 0.0131(10) 0.0087(10) C12 0.0259(14) 0.0189(12) 0.0195(12) 0.0059(10) 0.0135(11) 0.0087(10) C13 0.0174(12) 0.0170(12) 0.0137(12) 0.0005(10) 0.0046(10) 0.0018(10) C14 0.0147(12) 0.0160(11) 0.0146(12) 0.0046(9) 0.0051(9) 0.0045(9) C15 0.0152(13) 0.0262(15) 0.0209(15) 0.0005(11) 0.0043(11) 0.0036(11) C16 0.0375(18) 0.0300(16) 0.0317(17) -0.0012(13) 0.0220(15) 0.0088(14) C17 0.0146(12) 0.0186(13) 0.0170(13) 0.0010(10) 0.0030(10) 0.0029(10) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 C8 1.714(3) . ? S1 C5 1.720(2) . ? C1 C3 1.363(3) 2_656 ? C1 C2 1.418(3) . ? C1 H1 0.93(3) . ? C2 C6 1.398(3) . ? C2 C3 1.456(3) . ? C3 C1 1.363(3) 2_656 ? C3 C4 1.461(3) . ? C4 C5 1.384(3) . ? C4 C7 1.425(3) . ? C5 C6 1.447(3) . ? C6 C9 1.477(3) . ? C7 C8 1.357(4) . ? C7 H7 0.70(3) . ? C8 H8 0.88(3) . ? C9 C14 1.404(3) . ? C9 C10 1.409(3) . ? C10 C11 1.392(3) . ? C10 C15 1.502(3) . ? C11 C12 1.377(4) . ? C11 H11 0.91(3) . ? C12 C13 1.390(3) . ? C12 C16 1.508(4) . ? C13 C14 1.392(3) . ? C13 H13 0.96(3) . ? C14 C17 1.500(3) . ? C15 H15A 0.89(4) . ? C15 H15B 0.88(4) . ? C15 H15C 0.87(4) . ? C16 H16A 0.93(5) . ? C16 H16B 0.82(4) . ? C16 H16C 1.00(3) . ? C17 H17A 0.92(3) . ? C17 H17B 0.95(3) . ? C17 H17C 0.95(3) . ? 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 C8 S1 C5 90.90(12) . . ? C3 C1 C2 118.3(2) 2_656 . ? C3 C1 H1 120.4(16) 2_656 . ? C2 C1 H1 121.2(16) . . ? C6 C2 C1 129.9(2) . . ? C6 C2 C3 109.7(2) . . ? C1 C2 C3 120.3(2) . . ? C1 C3 C2 121.4(2) 2_656 . ? C1 C3 C4 132.5(2) 2_656 . ? C2 C3 C4 106.13(18) . . ? C5 C4 C7 112.8(2) . . ? C5 C4 C3 107.0(2) . . ? C7 C4 C3 140.2(2) . . ? C4 C5 C6 111.2(2) . . ? C4 C5 S1 111.44(17) . . ? C6 C5 S1 137.32(18) . . ? C2 C6 C5 105.9(2) . . ? C2 C6 C9 126.7(2) . . ? C5 C6 C9 127.3(2) . . ? C8 C7 C4 111.0(2) . . ? C8 C7 H7 126(2) . . ? C4 C7 H7 123(2) . . ? C7 C8 S1 113.87(19) . . ? C7 C8 H8 127.4(19) . . ? S1 C8 H8 118.7(19) . . ? C14 C9 C10 119.5(2) . . ? C14 C9 C6 120.2(2) . . ? C10 C9 C6 120.3(2) . . ? C11 C10 C9 118.8(2) . . ? C11 C10 C15 119.2(2) . . ? C9 C10 C15 121.9(2) . . ? C12 C11 C10 122.5(2) . . ? C12 C11 H11 119.9(16) . . ? C10 C11 H11 117.6(16) . . ? C11 C12 C13 118.1(2) . . ? C11 C12 C16 121.0(2) . . ? C13 C12 C16 120.9(2) . . ? C12 C13 C14 121.8(2) . . ? C12 C13 H13 117.9(15) . . ? C14 C13 H13 120.2(15) . . ? C13 C14 C9 119.3(2) . . ? C13 C14 C17 118.6(2) . . ? C9 C14 C17 122.1(2) . . ? C10 C15 H15A 112(2) . . ? C10 C15 H15B 113(2) . . ? H15A C15 H15B 108(3) . . ? C10 C15 H15C 112(2) . . ? H15A C15 H15C 98(3) . . ? H15B C15 H15C 112(3) . . ? C12 C16 H16A 113(3) . . ? C12 C16 H16B 112(3) . . ? H16A C16 H16B 97(3) . . ? C12 C16 H16C 112.4(17) . . ? H16A C16 H16C 115(3) . . ? H16B C16 H16C 106(3) . . ? C14 C17 H17A 109.5(18) . . ? C14 C17 H17B 111.4(16) . . ? H17A C17 H17B 107(2) . . ? C14 C17 H17C 112.5(17) . . ? H17A C17 H17C 109(2) . . ? H17B C17 H17C 108(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 C3 C1 C2 C6 179.9(2) 2_656 . . . ? C3 C1 C2 C3 0.5(3) 2_656 . . . ? C6 C2 C3 C1 180.0(2) . . . 2_656 ? C1 C2 C3 C1 -0.5(4) . . . 2_656 ? C6 C2 C3 C4 0.2(2) . . . . ? C1 C2 C3 C4 179.75(19) . . . . ? C1 C3 C4 C5 179.7(2) 2_656 . . . ? C2 C3 C4 C5 -0.6(2) . . . . ? C1 C3 C4 C7 -2.4(5) 2_656 . . . ? C2 C3 C4 C7 177.3(3) . . . . ? C7 C4 C5 C6 -177.75(19) . . . . ? C3 C4 C5 C6 0.8(3) . . . . ? C7 C4 C5 S1 0.0(3) . . . . ? C3 C4 C5 S1 178.62(15) . . . . ? C8 S1 C5 C4 0.24(18) . . . . ? C8 S1 C5 C6 177.2(3) . . . . ? C1 C2 C6 C5 -179.2(2) . . . . ? C3 C2 C6 C5 0.3(2) . . . . ? C1 C2 C6 C9 2.4(4) . . . . ? C3 C2 C6 C9 -178.1(2) . . . . ? C4 C5 C6 C2 -0.7(3) . . . . ? S1 C5 C6 C2 -177.7(2) . . . . ? C4 C5 C6 C9 177.6(2) . . . . ? S1 C5 C6 C9 0.7(4) . . . . ? C5 C4 C7 C8 -0.4(3) . . . . ? C3 C4 C7 C8 -178.3(3) . . . . ? C4 C7 C8 S1 0.6(3) . . . . ? C5 S1 C8 C7 -0.5(2) . . . . ? C2 C6 C9 C14 60.6(3) . . . . ? C5 C6 C9 C14 -117.4(3) . . . . ? C2 C6 C9 C10 -118.9(3) . . . . ? C5 C6 C9 C10 63.0(3) . . . . ? C14 C9 C10 C11 0.7(3) . . . . ? C6 C9 C10 C11 -179.7(2) . . . . ? C14 C9 C10 C15 -176.0(2) . . . . ? C6 C9 C10 C15 3.5(3) . . . . ? C9 C10 C11 C12 -1.0(3) . . . . ? C15 C10 C11 C12 175.8(2) . . . . ? C10 C11 C12 C13 0.1(3) . . . . ? C10 C11 C12 C16 -179.7(2) . . . . ? C11 C12 C13 C14 1.1(3) . . . . ? C16 C12 C13 C14 -179.0(2) . . . . ? C12 C13 C14 C9 -1.4(3) . . . . ? C12 C13 C14 C17 176.8(2) . . . . ? C10 C9 C14 C13 0.4(3) . . . . ? C6 C9 C14 C13 -179.1(2) . . . . ? C10 C9 C14 C17 -177.7(2) . . . . ? C6 C9 C14 C17 2.7(3) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.601 _refine_diff_density_min -0.366 _refine_diff_density_rms 0.060 _database_code_depnum_ccdc_archive 'CCDC 962726'