# Electronic Supplementary Material (ESI) for RSC Advances # 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_shelxl #TrackingRef 'ab_tm_603_r_0m.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C45.33 H26.67 O2.67 S1.33' _chemical_formula_weight 656.75 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' 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' _symmetry_cell_setting ? _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 14.159(4) _cell_length_b 14.219(4) _cell_length_c 15.690(4) _cell_angle_alpha 83.409(9) _cell_angle_beta 64.951(9) _cell_angle_gamma 65.669(8) _cell_volume 2600.7(12) _cell_formula_units_Z 3 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.2 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.258 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1024 _exptl_absorpt_coefficient_mu 0.154 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 35608 _diffrn_reflns_av_R_equivalents 0.2394 _diffrn_reflns_av_sigmaI/netI 0.4396 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.44 _diffrn_reflns_theta_max 28.58 _reflns_number_total 12282 _reflns_number_gt 2739 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1380P)^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 12282 _refine_ls_number_parameters 667 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.4118 _refine_ls_R_factor_gt 0.1252 _refine_ls_wR_factor_ref 0.3794 _refine_ls_wR_factor_gt 0.2441 _refine_ls_goodness_of_fit_ref 0.933 _refine_ls_restrained_S_all 0.933 _refine_ls_shift/su_max 0.303 _refine_ls_shift/su_mean 0.033 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 0.0392(2) 0.39485(19) 0.38598(18) 0.0595(7) Uani 1 1 d . . . S2 S 0.8777(2) -0.4385(2) -0.07190(18) 0.0700(8) Uani 1 1 d . . . C20 C 0.6371(7) -0.2264(6) 0.1303(6) 0.050(2) Uani 1 1 d . . . C55 C 0.2082(7) 0.1159(7) 0.5406(6) 0.048(2) Uani 1 1 d . . . C19 C 0.5889(7) -0.1199(7) 0.1134(6) 0.047(2) Uani 1 1 d . . . C11 C 0.4218(8) 0.0489(7) 0.1595(7) 0.056(2) Uani 1 1 d . . . C21 C 0.7428(7) -0.2908(7) 0.0614(6) 0.048(2) Uani 1 1 d . . . C18 C 0.5699(7) -0.2674(6) 0.2132(5) 0.047(2) Uani 1 1 d . . . C52 C 0.1938(7) 0.2663(6) 0.4387(6) 0.051(2) Uani 1 1 d . . . C16 C 0.4725(7) -0.0599(6) 0.1718(6) 0.046(2) Uani 1 1 d . . . O2 O 0.0418(5) 0.3340(5) 0.3172(4) 0.0702(18) Uani 1 1 d . . . C10 C 0.4939(9) 0.0931(7) 0.0875(7) 0.058(3) Uani 1 1 d . . . C63 C 0.0533(8) 0.1130(7) 0.6902(7) 0.056(2) Uani 1 1 d . . . C17 C 0.4530(7) -0.2163(7) 0.2525(6) 0.051(2) Uani 1 1 d . . . C50 C 0.2491(8) 0.3153(7) 0.3648(6) 0.052(2) Uani 1 1 d . . . C54 C 0.2611(7) 0.1691(7) 0.4626(6) 0.052(2) Uani 1 1 d . . . O1 O -0.0609(5) 0.4887(4) 0.4274(4) 0.0718(19) Uani 1 1 d . . . C45 C 0.3804(8) -0.0425(7) 0.4747(7) 0.059(3) Uani 1 1 d . . . C4 C 0.6539(8) -0.0776(7) 0.0403(7) 0.057(2) Uani 1 1 d . . . C15 C 0.4032(7) -0.1062(7) 0.2383(6) 0.050(2) Uani 1 1 d . . . C57 C 0.1880(9) -0.0470(7) 0.5886(7) 0.060(3) Uani 1 1 d . . . C14 C 0.2901(8) -0.0441(8) 0.2980(6) 0.066(3) Uani 1 1 d . . . H14 H 0.2454 -0.0730 0.3451 0.079 Uiso 1 1 calc R . . C62 C 0.0847(9) 0.0050(8) 0.6640(8) 0.065(3) Uani 1 1 d . . . C56 C 0.2605(8) 0.0077(7) 0.5336(6) 0.052(2) Uani 1 1 d . . . C47 C 0.3768(8) 0.1219(8) 0.4021(6) 0.058(3) Uani 1 1 d . . . O4 O 0.8063(6) -0.4285(5) -0.1185(4) 0.084(2) Uani 1 1 d . . . C41 C 0.5584(9) -0.0370(9) 0.3541(7) 0.070(3) Uani 1 1 d . . . C46 C 0.4399(8) 0.0130(7) 0.4119(6) 0.057(3) Uani 1 1 d . . . C34 C 0.6253(8) -0.3551(6) 0.2584(6) 0.050(2) Uani 1 1 d . . . C49 C 0.3660(9) 0.2755(8) 0.3155(7) 0.070(3) Uani 1 1 d . . . H49 H 0.4011 0.3138 0.2716 0.084 Uiso 1 1 calc R . . C48 C 0.4316(8) 0.1752(7) 0.3331(6) 0.058(3) Uani 1 1 d . . . C5 C 0.6066(9) 0.0341(8) 0.0281(7) 0.064(3) Uani 1 1 d . . . C13 C 0.2456(8) 0.0623(8) 0.2857(7) 0.069(3) Uani 1 1 d . . . H13 H 0.1711 0.1040 0.3254 0.082 Uiso 1 1 calc R . . C44 C 0.4435(9) -0.1452(7) 0.4899(7) 0.075(3) Uani 1 1 d . . . H44 H 0.4070 -0.1810 0.5360 0.090 Uiso 1 1 calc R . . C68 C 0.1123(7) 0.1677(7) 0.6273(6) 0.047(2) Uani 1 1 d . . . C12 C 0.3092(9) 0.1050(8) 0.2170(8) 0.069(3) Uani 1 1 d . . . H12 H 0.2758 0.1748 0.2082 0.083 Uiso 1 1 calc R . . O3 O 0.9773(5) -0.5339(5) -0.0897(4) 0.086(2) Uani 1 1 d . . . C3 C 0.7623(8) -0.1435(8) -0.0231(6) 0.062(3) Uani 1 1 d . . . H3 H 0.8070 -0.1157 -0.0717 0.074 Uiso 1 1 calc R . . C67 C 0.0884(8) 0.2674(7) 0.6575(7) 0.055(2) Uani 1 1 d . . . H67 H 0.1307 0.3030 0.6176 0.066 Uiso 1 1 calc R . . C64 C -0.0322(8) 0.1610(8) 0.7783(8) 0.071(3) Uani 1 1 d . . . H64 H -0.0729 0.1250 0.8196 0.086 Uiso 1 1 calc R . . C2 C 0.8040(7) -0.2490(7) -0.0145(6) 0.056(2) Uani 1 1 d . . . C37 C 0.6148(9) 0.0225(10) 0.2869(8) 0.075(3) Uani 1 1 d . . . C29 C 0.5604(8) -0.4052(7) 0.3216(6) 0.063(3) Uani 1 1 d . . . C42 C 0.6157(8) -0.1393(8) 0.3677(8) 0.072(3) Uani 1 1 d . . . H42 H 0.6933 -0.1734 0.3307 0.087 Uiso 1 1 calc R . . C23 C 0.3881(8) -0.2781(8) 0.3041(6) 0.064(3) Uani 1 1 d . . . C38 C 0.5561(9) 0.1248(9) 0.2742(7) 0.074(3) Uani 1 1 d . . . C22 C 0.7924(7) -0.4086(6) 0.0500(6) 0.061(3) Uani 1 1 d . . . H22A H 0.7323 -0.4334 0.0708 0.073 Uiso 1 1 calc R . . H22B H 0.8378 -0.4391 0.0860 0.073 Uiso 1 1 calc R . . C53 C 0.0658(7) 0.3141(6) 0.4768(6) 0.058(2) Uani 1 1 d . . . H53A H 0.0322 0.3546 0.5359 0.070 Uiso 1 1 calc R . . H53B H 0.0359 0.2615 0.4866 0.070 Uiso 1 1 calc R . . C51 C 0.1667(7) 0.4146(7) 0.3409(6) 0.063(3) Uani 1 1 d . . . H51A H 0.1941 0.4212 0.2734 0.076 Uiso 1 1 calc R . . H51B H 0.1562 0.4758 0.3717 0.076 Uiso 1 1 calc R . . C28 C 0.4426(9) -0.3725(8) 0.3379(6) 0.065(3) Uani 1 1 d . . . C33 C 0.7346(7) -0.3806(7) 0.2504(6) 0.059(3) Uani 1 1 d . . . H33 H 0.7765 -0.3448 0.2104 0.071 Uiso 1 1 calc R . . C61 C 0.0136(9) -0.0464(9) 0.7127(8) 0.083(3) Uani 1 1 d . . . H61 H -0.0542 -0.0126 0.7647 0.099 Uiso 1 1 calc R . . C32 C 0.7822(8) -0.4561(8) 0.2992(7) 0.073(3) Uani 1 1 d . . . H32 H 0.8559 -0.4723 0.2923 0.087 Uiso 1 1 calc R . . C65 C -0.0573(9) 0.2601(9) 0.8051(8) 0.083(3) Uani 1 1 d . . . H65 H -0.1152 0.2914 0.8634 0.100 Uiso 1 1 calc R . . C9 C 0.4490(10) 0.2001(8) 0.0721(8) 0.082(3) Uani 1 1 d . . . H9 H 0.3726 0.2409 0.1079 0.099 Uiso 1 1 calc R . . C60 C 0.2125(10) -0.1478(8) 0.5584(8) 0.077(3) Uani 1 1 d . . . H60 H 0.2780 -0.1817 0.5047 0.093 Uiso 1 1 calc R . . C66 C 0.0055(9) 0.3135(8) 0.7433(8) 0.070(3) Uani 1 1 d . . . H66 H -0.0094 0.3802 0.7609 0.084 Uiso 1 1 calc R . . C8 C 0.5161(14) 0.2450(10) 0.0055(10) 0.099(4) Uani 1 1 d . . . H8 H 0.4850 0.3157 -0.0011 0.119 Uiso 1 1 calc R . . C1 C 0.9110(8) -0.3289(7) -0.0883(6) 0.070(3) Uani 1 1 d . . . H1A H 0.9776 -0.3430 -0.0768 0.085 Uiso 1 1 calc R . . H1B H 0.9242 -0.3062 -0.1515 0.085 Uiso 1 1 calc R . . C7 C 0.6277(13) 0.1868(10) -0.0511(9) 0.100(4) Uani 1 1 d . . . H7 H 0.6723 0.2166 -0.0971 0.120 Uiso 1 1 calc R . . C43 C 0.5587(10) -0.1915(8) 0.4361(8) 0.076(3) Uani 1 1 d . . . H43 H 0.5994 -0.2592 0.4455 0.092 Uiso 1 1 calc R . . C24 C 0.2783(9) -0.2535(9) 0.3123(7) 0.078(3) Uani 1 1 d . . . H24 H 0.2442 -0.1940 0.2865 0.094 Uiso 1 1 calc R . . C6 C 0.6724(9) 0.0824(8) -0.0380(7) 0.073(3) Uani 1 1 d . . . H6 H 0.7489 0.0428 -0.0744 0.087 Uiso 1 1 calc R . . C59 C 0.0426(12) -0.1456(10) 0.6848(11) 0.101(4) Uani 1 1 d . . . H59 H -0.0045 -0.1796 0.7185 0.121 Uiso 1 1 calc R . . C31 C 0.7203(10) -0.5076(8) 0.3584(8) 0.092(4) Uani 1 1 d . . . H31 H 0.7534 -0.5608 0.3905 0.111 Uiso 1 1 calc R . . C27 C 0.3764(11) -0.4312(9) 0.3846(7) 0.090(3) Uani 1 1 d . . . H27 H 0.4098 -0.4935 0.4076 0.108 Uiso 1 1 calc R . . C30 C 0.6109(10) -0.4835(8) 0.3719(7) 0.088(3) Uani 1 1 d . . . H30 H 0.5697 -0.5185 0.4141 0.106 Uiso 1 1 calc R . . C36 C 0.7324(11) -0.0262(11) 0.2282(9) 0.109(4) Uani 1 1 d . . . H36 H 0.7722 -0.0963 0.2317 0.130 Uiso 1 1 calc R . . C58 C 0.1418(13) -0.1954(9) 0.6063(11) 0.095(4) Uani 1 1 d . . . H58 H 0.1602 -0.2622 0.5863 0.114 Uiso 1 1 calc R . . C25 C 0.2179(10) -0.3137(11) 0.3571(8) 0.096(4) Uani 1 1 d . . . H25 H 0.1454 -0.2958 0.3603 0.115 Uiso 1 1 calc R . . C35 C 0.7882(11) 0.0291(14) 0.1660(10) 0.127(5) Uani 1 1 d . . . H35 H 0.8658 -0.0041 0.1286 0.153 Uiso 1 1 calc R . . C39 C 0.6143(11) 0.1817(10) 0.2107(9) 0.106(4) Uani 1 1 d . . . H39 H 0.5742 0.2509 0.2046 0.127 Uiso 1 1 calc R . . C40 C 0.7314(11) 0.1345(14) 0.1573(9) 0.135(6) Uani 1 1 d . . . H40 H 0.7708 0.1719 0.1169 0.162 Uiso 1 1 calc R . . C26 C 0.2676(11) -0.4004(10) 0.3968(8) 0.092(4) Uani 1 1 d . . . H26 H 0.2258 -0.4382 0.4324 0.110 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 0.0675(17) 0.0564(16) 0.0676(18) 0.0202(13) -0.0442(15) -0.0240(13) S2 0.0631(18) 0.0746(19) 0.0582(19) -0.0020(14) -0.0256(15) -0.0126(15) C20 0.043(6) 0.054(6) 0.046(6) 0.003(5) -0.025(5) -0.005(5) C55 0.049(6) 0.049(6) 0.045(6) -0.001(5) -0.024(5) -0.013(5) C19 0.040(5) 0.061(6) 0.042(6) 0.016(5) -0.025(5) -0.017(5) C11 0.056(7) 0.060(7) 0.052(6) 0.008(5) -0.034(6) -0.014(6) C21 0.041(6) 0.056(6) 0.036(5) 0.005(5) -0.016(5) -0.010(5) C18 0.063(6) 0.064(6) 0.032(5) 0.019(5) -0.035(5) -0.029(5) C52 0.052(6) 0.056(6) 0.049(6) 0.009(5) -0.030(5) -0.019(5) C16 0.044(6) 0.050(6) 0.049(6) 0.007(5) -0.034(5) -0.010(5) O2 0.093(5) 0.071(4) 0.068(4) 0.018(4) -0.050(4) -0.039(4) C10 0.069(7) 0.045(6) 0.059(7) -0.004(5) -0.043(6) -0.006(6) C63 0.050(6) 0.046(6) 0.067(7) 0.007(6) -0.030(6) -0.010(5) C17 0.036(5) 0.074(7) 0.039(5) 0.009(5) -0.019(5) -0.017(5) C50 0.052(6) 0.060(6) 0.051(6) 0.008(5) -0.028(5) -0.023(5) C54 0.045(6) 0.059(6) 0.053(6) 0.000(5) -0.026(5) -0.016(5) O1 0.066(4) 0.055(4) 0.090(5) 0.014(3) -0.049(4) -0.006(3) C45 0.071(7) 0.065(7) 0.051(6) 0.007(6) -0.046(6) -0.015(6) C4 0.054(7) 0.058(7) 0.056(7) 0.000(5) -0.024(6) -0.018(6) C15 0.037(6) 0.063(6) 0.041(6) 0.002(5) -0.019(5) -0.009(5) C57 0.075(8) 0.041(6) 0.074(8) 0.015(6) -0.049(7) -0.018(6) C14 0.050(7) 0.084(8) 0.062(7) 0.001(6) -0.030(6) -0.018(6) C62 0.077(8) 0.059(7) 0.078(8) 0.032(6) -0.048(7) -0.034(7) C56 0.049(6) 0.051(6) 0.049(6) 0.004(5) -0.028(5) -0.007(5) C47 0.061(7) 0.075(7) 0.049(6) 0.007(6) -0.028(6) -0.031(6) O4 0.094(5) 0.088(5) 0.075(5) 0.009(4) -0.042(4) -0.036(4) C41 0.061(8) 0.096(9) 0.061(7) -0.002(7) -0.038(6) -0.022(7) C46 0.057(7) 0.067(7) 0.047(6) -0.002(5) -0.033(6) -0.010(6) C34 0.058(6) 0.056(6) 0.036(5) 0.003(5) -0.023(5) -0.018(5) C49 0.073(8) 0.093(8) 0.063(7) 0.019(6) -0.031(6) -0.050(7) C48 0.052(6) 0.069(7) 0.054(7) 0.004(6) -0.030(5) -0.016(6) C5 0.088(8) 0.057(7) 0.053(7) 0.016(6) -0.035(6) -0.032(7) C13 0.050(6) 0.079(8) 0.069(8) -0.002(6) -0.033(6) -0.009(6) C44 0.069(8) 0.065(7) 0.076(8) -0.010(6) -0.043(7) 0.003(6) C68 0.049(6) 0.052(6) 0.044(6) 0.014(5) -0.025(5) -0.022(5) C12 0.063(8) 0.058(7) 0.083(8) 0.004(6) -0.042(7) -0.009(6) O3 0.076(5) 0.076(5) 0.083(5) -0.021(4) -0.033(4) -0.002(4) C3 0.069(7) 0.075(7) 0.053(7) 0.022(6) -0.031(6) -0.037(6) C67 0.049(6) 0.051(6) 0.061(7) 0.005(5) -0.025(6) -0.014(5) C64 0.058(7) 0.065(7) 0.076(8) 0.008(6) -0.028(6) -0.012(6) C2 0.050(6) 0.065(7) 0.049(6) 0.009(5) -0.026(5) -0.016(5) C37 0.038(7) 0.115(10) 0.074(8) -0.009(7) -0.035(6) -0.017(7) C29 0.067(7) 0.061(6) 0.057(7) 0.012(5) -0.029(6) -0.020(6) C42 0.051(7) 0.068(8) 0.088(9) -0.025(7) -0.040(7) 0.005(6) C23 0.070(7) 0.083(7) 0.047(6) 0.018(5) -0.028(6) -0.038(6) C38 0.059(8) 0.103(9) 0.064(8) 0.009(7) -0.039(6) -0.024(7) C22 0.051(6) 0.057(6) 0.054(6) 0.006(5) -0.021(5) -0.004(5) C53 0.068(7) 0.048(5) 0.064(6) 0.023(5) -0.040(5) -0.020(5) C51 0.079(7) 0.064(6) 0.062(7) 0.014(5) -0.032(6) -0.043(5) C28 0.073(7) 0.068(7) 0.060(7) 0.012(5) -0.033(6) -0.030(6) C33 0.058(6) 0.068(6) 0.041(6) 0.012(5) -0.028(5) -0.010(5) C61 0.078(8) 0.070(8) 0.100(9) 0.021(7) -0.044(7) -0.027(7) C32 0.057(7) 0.081(7) 0.070(7) 0.023(6) -0.033(6) -0.016(6) C65 0.076(8) 0.071(8) 0.080(8) -0.001(7) -0.025(7) -0.017(7) C9 0.096(9) 0.063(8) 0.103(9) 0.007(7) -0.071(8) -0.016(7) C60 0.102(9) 0.048(7) 0.089(8) 0.023(6) -0.056(7) -0.024(7) C66 0.063(7) 0.064(7) 0.085(8) 0.011(7) -0.036(7) -0.023(6) C8 0.151(13) 0.077(9) 0.110(11) 0.046(9) -0.091(11) -0.055(10) C1 0.067(7) 0.075(7) 0.065(7) 0.013(6) -0.024(6) -0.028(6) C7 0.145(12) 0.079(10) 0.096(10) 0.044(8) -0.061(10) -0.063(9) C43 0.088(9) 0.068(8) 0.083(9) 0.001(7) -0.056(8) -0.019(7) C24 0.064(7) 0.115(9) 0.069(8) 0.008(7) -0.038(6) -0.038(7) C6 0.087(8) 0.074(8) 0.056(7) 0.009(6) -0.033(6) -0.030(7) C59 0.107(11) 0.057(9) 0.162(14) 0.038(8) -0.078(10) -0.038(8) C31 0.091(9) 0.085(8) 0.097(9) 0.047(7) -0.057(8) -0.026(7) C27 0.111(10) 0.088(8) 0.087(9) 0.026(7) -0.042(8) -0.058(8) C30 0.107(10) 0.085(8) 0.074(8) 0.036(6) -0.044(8) -0.042(7) C36 0.080(10) 0.167(13) 0.094(10) 0.039(10) -0.057(9) -0.051(10) C58 0.119(11) 0.046(7) 0.146(13) 0.025(8) -0.090(10) -0.025(8) C25 0.090(9) 0.150(12) 0.087(9) 0.013(8) -0.049(8) -0.073(9) C35 0.053(9) 0.171(16) 0.120(13) 0.003(11) -0.036(9) -0.010(10) C39 0.087(10) 0.150(12) 0.103(10) 0.049(9) -0.049(8) -0.069(10) C40 0.042(8) 0.200(17) 0.118(12) 0.022(11) -0.010(8) -0.035(9) C26 0.096(10) 0.133(11) 0.082(9) 0.024(8) -0.040(8) -0.080(9) _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 O2 1.438(6) . ? S1 O1 1.440(6) . ? S1 C51 1.769(8) . ? S1 C53 1.793(7) . ? S2 O4 1.435(6) . ? S2 O3 1.444(6) . ? S2 C1 1.768(9) . ? S2 C22 1.763(8) . ? C20 C21 1.405(10) . ? C20 C19 1.428(10) . ? C20 C18 1.474(11) . ? C55 C56 1.400(11) . ? C55 C68 1.442(11) . ? C55 C54 1.452(11) . ? C19 C4 1.388(11) . ? C19 C16 1.423(10) . ? C11 C12 1.375(11) . ? C11 C10 1.449(12) . ? C11 C16 1.443(11) . ? C21 C2 1.382(11) . ? C21 C22 1.524(10) . ? C18 C17 1.376(10) . ? C18 C34 1.462(10) . ? C52 C50 1.393(11) . ? C52 C54 1.435(11) . ? C52 C53 1.504(10) . ? C16 C15 1.412(11) . ? C10 C5 1.392(12) . ? C10 C9 1.424(12) . ? C63 C68 1.392(11) . ? C63 C64 1.401(12) . ? C63 C62 1.467(12) . ? C17 C23 1.465(11) . ? C17 C15 1.464(11) . ? C50 C49 1.380(11) . ? C50 C51 1.544(11) . ? C54 C47 1.399(11) . ? C45 C46 1.403(12) . ? C45 C44 1.419(11) . ? C45 C56 1.439(11) . ? C4 C3 1.400(11) . ? C4 C5 1.474(12) . ? C15 C14 1.405(11) . ? C57 C62 1.389(12) . ? C57 C60 1.416(12) . ? C57 C56 1.468(12) . ? C14 C13 1.405(12) . ? C62 C61 1.400(12) . ? C47 C48 1.391(12) . ? C47 C46 1.464(12) . ? C41 C42 1.387(12) . ? C41 C46 1.421(12) . ? C41 C37 1.450(14) . ? C34 C29 1.393(11) . ? C34 C33 1.388(10) . ? C49 C48 1.416(12) . ? C48 C38 1.486(12) . ? C5 C6 1.400(12) . ? C13 C12 1.349(12) . ? C44 C43 1.372(12) . ? C68 C67 1.403(11) . ? C3 C2 1.382(11) . ? C67 C66 1.361(11) . ? C64 C65 1.373(12) . ? C2 C1 1.525(11) . ? C37 C38 1.387(13) . ? C37 C36 1.414(14) . ? C29 C30 1.412(12) . ? C29 C28 1.447(12) . ? C42 C43 1.389(12) . ? C23 C24 1.396(12) . ? C23 C28 1.417(12) . ? C38 C39 1.411(13) . ? C28 C27 1.425(12) . ? C33 C32 1.358(11) . ? C61 C59 1.365(13) . ? C32 C31 1.361(12) . ? C65 C66 1.402(12) . ? C9 C8 1.381(14) . ? C60 C58 1.352(13) . ? C8 C7 1.369(15) . ? C7 C6 1.383(13) . ? C24 C25 1.383(13) . ? C59 C58 1.380(15) . ? C31 C30 1.365(13) . ? C27 C26 1.347(13) . ? C36 C35 1.370(16) . ? C25 C26 1.372(14) . ? C35 C40 1.401(17) . ? C39 C40 1.392(14) . ? 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 O2 S1 O1 117.5(4) . . ? O2 S1 C51 109.6(4) . . ? O1 S1 C51 112.6(4) . . ? O2 S1 C53 108.8(4) . . ? O1 S1 C53 110.0(4) . . ? C51 S1 C53 96.2(4) . . ? O4 S2 O3 118.0(4) . . ? O4 S2 C1 109.8(4) . . ? O3 S2 C1 112.0(4) . . ? O4 S2 C22 108.7(4) . . ? O3 S2 C22 111.1(4) . . ? C1 S2 C22 94.6(4) . . ? C21 C20 C19 118.1(8) . . ? C21 C20 C18 122.1(8) . . ? C19 C20 C18 119.4(8) . . ? C56 C55 C68 118.5(8) . . ? C56 C55 C54 117.3(8) . . ? C68 C55 C54 124.0(8) . . ? C4 C19 C16 121.5(8) . . ? C4 C19 C20 120.3(8) . . ? C16 C19 C20 118.2(8) . . ? C12 C11 C10 123.8(9) . . ? C12 C11 C16 118.6(9) . . ? C10 C11 C16 117.5(9) . . ? C2 C21 C20 120.3(8) . . ? C2 C21 C22 112.4(8) . . ? C20 C21 C22 126.4(8) . . ? C17 C18 C34 119.9(8) . . ? C17 C18 C20 118.7(7) . . ? C34 C18 C20 121.2(8) . . ? C50 C52 C54 118.5(8) . . ? C50 C52 C53 115.3(7) . . ? C54 C52 C53 125.6(8) . . ? C15 C16 C19 121.2(8) . . ? C15 C16 C11 118.8(8) . . ? C19 C16 C11 119.9(8) . . ? C5 C10 C11 122.8(9) . . ? C5 C10 C9 116.9(10) . . ? C11 C10 C9 120.3(10) . . ? C68 C63 C64 119.3(9) . . ? C68 C63 C62 119.3(9) . . ? C64 C63 C62 121.4(10) . . ? C18 C17 C23 116.7(8) . . ? C18 C17 C15 118.2(8) . . ? C23 C17 C15 125.1(8) . . ? C49 C50 C52 122.6(8) . . ? C49 C50 C51 123.9(8) . . ? C52 C50 C51 113.4(8) . . ? C47 C54 C52 117.8(8) . . ? C47 C54 C55 121.0(8) . . ? C52 C54 C55 120.8(8) . . ? C46 C45 C44 118.5(10) . . ? C46 C45 C56 121.1(9) . . ? C44 C45 C56 119.7(10) . . ? C19 C4 C3 118.9(9) . . ? C19 C4 C5 120.0(9) . . ? C3 C4 C5 121.0(9) . . ? C14 C15 C16 119.7(9) . . ? C14 C15 C17 120.1(9) . . ? C16 C15 C17 119.8(8) . . ? C62 C57 C60 118.1(10) . . ? C62 C57 C56 120.0(9) . . ? C60 C57 C56 121.2(10) . . ? C15 C14 C13 119.1(9) . . ? C57 C62 C61 119.5(10) . . ? C57 C62 C63 118.7(9) . . ? C61 C62 C63 121.8(11) . . ? C55 C56 C45 118.6(9) . . ? C55 C56 C57 117.0(8) . . ? C45 C56 C57 124.4(9) . . ? C54 C47 C48 121.8(9) . . ? C54 C47 C46 118.3(9) . . ? C48 C47 C46 120.0(9) . . ? C42 C41 C46 118.2(11) . . ? C42 C41 C37 123.1(11) . . ? C46 C41 C37 118.7(10) . . ? C45 C46 C41 120.8(10) . . ? C45 C46 C47 119.0(9) . . ? C41 C46 C47 120.1(10) . . ? C29 C34 C33 119.0(8) . . ? C29 C34 C18 118.3(8) . . ? C33 C34 C18 122.0(8) . . ? C50 C49 C48 118.8(9) . . ? C47 C48 C49 119.1(9) . . ? C47 C48 C38 120.3(9) . . ? C49 C48 C38 120.4(9) . . ? C10 C5 C6 119.7(10) . . ? C10 C5 C4 118.0(9) . . ? C6 C5 C4 122.3(10) . . ? C12 C13 C14 121.0(10) . . ? C43 C44 C45 119.6(11) . . ? C63 C68 C67 118.2(9) . . ? C63 C68 C55 119.8(9) . . ? C67 C68 C55 121.1(8) . . ? C13 C12 C11 122.3(10) . . ? C2 C3 C4 121.0(9) . . ? C66 C67 C68 122.0(9) . . ? C65 C64 C63 121.5(10) . . ? C3 C2 C21 120.4(9) . . ? C3 C2 C1 125.0(9) . . ? C21 C2 C1 114.4(8) . . ? C38 C37 C36 118.2(12) . . ? C38 C37 C41 122.3(10) . . ? C36 C37 C41 119.4(12) . . ? C34 C29 C30 118.3(9) . . ? C34 C29 C28 119.8(8) . . ? C30 C29 C28 121.8(9) . . ? C41 C42 C43 120.8(10) . . ? C24 C23 C28 118.2(9) . . ? C24 C23 C17 122.3(9) . . ? C28 C23 C17 119.1(9) . . ? C37 C38 C39 120.9(11) . . ? C37 C38 C48 118.4(10) . . ? C39 C38 C48 120.6(11) . . ? C21 C22 S2 104.2(6) . . ? C52 C53 S1 103.1(6) . . ? C50 C51 S1 102.6(6) . . ? C27 C28 C23 116.6(9) . . ? C27 C28 C29 124.0(10) . . ? C23 C28 C29 119.4(9) . . ? C32 C33 C34 122.1(9) . . ? C59 C61 C62 120.8(11) . . ? C33 C32 C31 118.9(9) . . ? C64 C65 C66 119.1(10) . . ? C8 C9 C10 121.7(11) . . ? C58 C60 C57 120.9(11) . . ? C67 C66 C65 119.7(10) . . ? C7 C8 C9 120.9(12) . . ? C2 C1 S2 102.3(6) . . ? C8 C7 C6 118.2(12) . . ? C44 C43 C42 121.4(10) . . ? C23 C24 C25 123.0(10) . . ? C7 C6 C5 122.4(11) . . ? C61 C59 C58 119.8(12) . . ? C32 C31 C30 121.8(10) . . ? C26 C27 C28 122.9(11) . . ? C31 C30 C29 119.9(10) . . ? C35 C36 C37 120.5(13) . . ? C60 C58 C59 120.6(12) . . ? C26 C25 C24 118.3(10) . . ? C36 C35 C40 121.7(13) . . ? C40 C39 C38 120.2(13) . . ? C39 C40 C35 118.3(14) . . ? C27 C26 C25 120.6(11) . . ? _diffrn_measured_fraction_theta_max 0.926 _diffrn_reflns_theta_full 28.58 _diffrn_measured_fraction_theta_full 0.926 _refine_diff_density_max 0.752 _refine_diff_density_min -0.341 _refine_diff_density_rms 0.076 _database_code_depnum_ccdc_archive 'CCDC 930529' ####################################################################### # # 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_shelxl _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H16 N0 O2 S' _chemical_formula_weight 344.41 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' _symmetry_cell_setting ? _symmetry_space_group_name_H-M ? loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 11.693(2) _cell_length_b 12.779(2) _cell_length_c 12.838(2) _cell_angle_alpha 82.653(6) _cell_angle_beta 67.803(5) _cell_angle_gamma 73.719(5) _cell_volume 1704.4(5) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.342 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 720 _exptl_absorpt_coefficient_mu 0.202 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 20319 _diffrn_reflns_av_R_equivalents 0.0813 _diffrn_reflns_av_sigmaI/netI 0.0903 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.66 _diffrn_reflns_theta_max 25.06 _reflns_number_total 5983 _reflns_number_gt 3362 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0917P)^2^+0.4358P] 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 5983 _refine_ls_number_parameters 451 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1374 _refine_ls_R_factor_gt 0.0729 _refine_ls_wR_factor_ref 0.1990 _refine_ls_wR_factor_gt 0.1641 _refine_ls_goodness_of_fit_ref 1.014 _refine_ls_restrained_S_all 1.014 _refine_ls_shift/su_max 0.020 _refine_ls_shift/su_mean 0.003 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 0.55322(9) 0.80396(9) 0.04146(10) 0.0488(3) Uani 1 1 d . . . O3 O 0.4447(3) 0.8837(2) 0.0270(3) 0.0671(9) Uani 1 1 d . . . C37 C 0.7642(3) 0.6820(3) -0.0903(3) 0.0403(10) Uani 1 1 d . . . C24 C 0.7993(3) 0.7623(3) -0.0531(3) 0.0404(10) Uani 1 1 d . . . C32 C 1.2408(4) 0.5439(3) -0.1738(3) 0.0447(10) Uani 1 1 d . . . O4 O 0.5332(3) 0.7486(3) 0.1486(3) 0.0676(9) Uani 1 1 d . . . C26 C 1.0190(3) 0.6588(3) -0.1191(3) 0.0384(9) Uani 1 1 d . . . C35 C 0.9831(3) 0.5753(3) -0.1519(3) 0.0411(10) Uani 1 1 d . . . C36 C 0.8540(3) 0.5901(3) -0.1422(3) 0.0397(10) Uani 1 1 d . . . C39 C 0.8129(3) 0.5116(3) -0.1899(3) 0.0395(10) Uani 1 1 d . . . C38 C 0.6224(3) 0.7060(3) -0.0666(4) 0.0454(11) Uani 1 1 d . . . H38A H 0.5919 0.6406 -0.0409 0.054 Uiso 1 1 calc R . . H38B H 0.6030 0.7356 -0.1331 0.054 Uiso 1 1 calc R . . C27 C 1.1533(4) 0.6448(3) -0.1353(3) 0.0401(10) Uani 1 1 d . . . C34 C 1.0765(4) 0.4746(3) -0.1912(4) 0.0476(11) Uani 1 1 d . . . H34 H 1.0526 0.4196 -0.2127 0.057 Uiso 1 1 calc R . . C25 C 0.9249(3) 0.7521(3) -0.0695(3) 0.0417(10) Uani 1 1 d . . . H25 H 0.9478 0.8075 -0.0475 0.050 Uiso 1 1 calc R . . C28 C 1.1995(4) 0.7286(3) -0.1176(3) 0.0472(11) Uani 1 1 d . . . H28 H 1.1430 0.7954 -0.0923 0.057 Uiso 1 1 calc R . . C33 C 1.1979(4) 0.4582(3) -0.1975(4) 0.0504(11) Uani 1 1 d . . . H33 H 1.2547 0.3903 -0.2174 0.060 Uiso 1 1 calc R . . C23 C 0.6894(3) 0.8566(3) 0.0038(4) 0.0484(11) Uani 1 1 d . . . H23A H 0.6844 0.9191 -0.0474 0.058 Uiso 1 1 calc R . . H23B H 0.6979 0.8778 0.0698 0.058 Uiso 1 1 calc R . . C30 C 1.4132(4) 0.6131(4) -0.1753(4) 0.0574(12) Uani 1 1 d . . . H30 H 1.4995 0.6033 -0.1891 0.069 Uiso 1 1 calc R . . C29 C 1.3273(4) 0.7134(4) -0.1371(4) 0.0577(12) Uani 1 1 d . . . H29 H 1.3563 0.7698 -0.1250 0.069 Uiso 1 1 calc R . . C31 C 1.3715(4) 0.5300(4) -0.1922(4) 0.0528(12) Uani 1 1 d . . . H31 H 1.4293 0.4633 -0.2161 0.063 Uiso 1 1 calc R . . C44 C 0.7567(4) 0.4336(4) -0.1240(4) 0.0534(12) Uani 1 1 d . . . H44 H 0.7475 0.4256 -0.0485 0.064 Uiso 1 1 calc R . . C42 C 0.7263(4) 0.3766(4) -0.2795(5) 0.0660(14) Uani 1 1 d . . . H42 H 0.6963 0.3320 -0.3095 0.079 Uiso 1 1 calc R . . C43 C 0.7132(4) 0.3661(4) -0.1694(5) 0.0632(13) Uani 1 1 d . . . H43 H 0.6749 0.3135 -0.1239 0.076 Uiso 1 1 calc R . . C40 C 0.8274(5) 0.5198(4) -0.3015(4) 0.0659(14) Uani 1 1 d . . . H40 H 0.8671 0.5712 -0.3480 0.079 Uiso 1 1 calc R . . C41 C 0.7838(6) 0.4531(5) -0.3455(5) 0.0822(17) Uani 1 1 d . . . H41 H 0.7937 0.4603 -0.4212 0.099 Uiso 1 1 calc R . . S2 S 0.87577(12) 0.91567(11) 0.19576(12) 0.0663(4) Uani 1 1 d . . . C3 C 1.1417(4) 0.9987(3) 0.2621(4) 0.0511(11) Uani 1 1 d . . . H3 H 1.2219 0.9599 0.2168 0.061 Uiso 1 1 calc R . . C14 C 0.8969(4) 1.1184(3) 0.3920(3) 0.0447(10) Uani 1 1 d . . . C17 C 0.7672(4) 1.1888(3) 0.4508(3) 0.0444(10) Uani 1 1 d . . . C5 C 1.2431(4) 1.1064(3) 0.3361(3) 0.0465(10) Uani 1 1 d . . . C15 C 0.9128(4) 1.0354(3) 0.3252(4) 0.0496(11) Uani 1 1 d . . . C4 C 1.1319(4) 1.0801(3) 0.3309(3) 0.0450(10) Uani 1 1 d . . . C2 C 1.0357(4) 0.9756(3) 0.2605(4) 0.0509(11) Uani 1 1 d . . . O1 O 0.8641(4) 0.9796(3) 0.0978(3) 0.0891(11) Uani 1 1 d . . . C13 C 1.0079(4) 1.1384(3) 0.3988(3) 0.0436(10) Uani 1 1 d . . . C18 C 0.7383(4) 1.2989(4) 0.4231(4) 0.0588(13) Uani 1 1 d . . . H18 H 0.8014 1.3296 0.3713 0.071 Uiso 1 1 calc R . . O2 O 0.8322(4) 0.8186(3) 0.2212(4) 0.0970(13) Uani 1 1 d . . . C10 C 1.2257(4) 1.1829(4) 0.4144(4) 0.0536(12) Uani 1 1 d . . . C1 C 1.0369(4) 0.8895(4) 0.1894(5) 0.0709(15) Uani 1 1 d . . . H1A H 1.0640 0.8171 0.2192 0.085 Uiso 1 1 calc R . . H1B H 1.0942 0.8954 0.1124 0.085 Uiso 1 1 calc R . . C16 C 0.8041(4) 1.0020(4) 0.3136(4) 0.0624(13) Uani 1 1 d . . . H16A H 0.7417 1.0655 0.3007 0.075 Uiso 1 1 calc R . . H16B H 0.7619 0.9633 0.3809 0.075 Uiso 1 1 calc R . . C12 C 0.9966(4) 1.2145(4) 0.4773(4) 0.0539(12) Uani 1 1 d . . . H12 H 0.9158 1.2513 0.5236 0.065 Uiso 1 1 calc R . . C7 C 1.4724(4) 1.0814(4) 0.2760(4) 0.0662(14) Uani 1 1 d . . . H7 H 1.5547 1.0477 0.2297 0.079 Uiso 1 1 calc R . . C11 C 1.1003(4) 1.2337(4) 0.4856(4) 0.0605(13) Uani 1 1 d . . . H11 H 1.0894 1.2815 0.5394 0.073 Uiso 1 1 calc R . . C19 C 0.6161(5) 1.3632(4) 0.4721(4) 0.0709(15) Uani 1 1 d . . . H19 H 0.5969 1.4366 0.4514 0.085 Uiso 1 1 calc R . . C6 C 1.3693(4) 1.0573(4) 0.2664(4) 0.0537(12) Uani 1 1 d . . . H6 H 1.3828 1.0078 0.2131 0.064 Uiso 1 1 calc R . . C9 C 1.3332(5) 1.2051(4) 0.4224(4) 0.0687(14) Uani 1 1 d . . . H9 H 1.3216 1.2545 0.4751 0.082 Uiso 1 1 calc R . . C21 C 0.5501(4) 1.2126(4) 0.5809(4) 0.0647(14) Uani 1 1 d . . . H21 H 0.4876 1.1830 0.6352 0.078 Uiso 1 1 calc R . . C8 C 1.4545(4) 1.1558(5) 0.3545(5) 0.0740(15) Uani 1 1 d . . . H8 H 1.5244 1.1719 0.3608 0.089 Uiso 1 1 calc R . . C20 C 0.5223(5) 1.3197(4) 0.5514(4) 0.0675(14) Uani 1 1 d . . . H20 H 0.4404 1.3636 0.5843 0.081 Uiso 1 1 calc R . . C22 C 0.6717(4) 1.1471(4) 0.5300(4) 0.0574(12) Uani 1 1 d . . . H22 H 0.6893 1.0733 0.5497 0.069 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 0.0322(6) 0.0429(7) 0.0714(8) -0.0221(6) -0.0171(5) -0.0028(5) O3 0.0345(16) 0.0517(19) 0.115(3) -0.0312(18) -0.0321(17) 0.0096(14) C37 0.031(2) 0.037(2) 0.056(3) -0.0153(19) -0.0174(18) -0.0040(18) C24 0.032(2) 0.032(2) 0.058(3) -0.0174(19) -0.0169(19) -0.0028(17) C32 0.032(2) 0.043(3) 0.056(3) -0.008(2) -0.0137(19) -0.0049(19) O4 0.068(2) 0.073(2) 0.062(2) -0.0060(18) -0.0149(16) -0.0267(18) C26 0.032(2) 0.036(2) 0.048(2) -0.0067(19) -0.0140(17) -0.0079(17) C35 0.032(2) 0.036(2) 0.057(3) -0.012(2) -0.0167(18) -0.0041(18) C36 0.036(2) 0.034(2) 0.051(2) -0.0115(19) -0.0167(18) -0.0069(18) C39 0.0258(19) 0.036(2) 0.054(3) -0.017(2) -0.0130(18) 0.0018(17) C38 0.032(2) 0.039(2) 0.070(3) -0.021(2) -0.022(2) -0.0033(18) C27 0.036(2) 0.041(2) 0.047(2) -0.0060(19) -0.0162(18) -0.0122(19) C34 0.035(2) 0.037(2) 0.072(3) -0.022(2) -0.017(2) -0.0040(19) C25 0.037(2) 0.037(2) 0.057(3) -0.013(2) -0.0201(19) -0.0085(18) C28 0.034(2) 0.050(3) 0.061(3) -0.010(2) -0.0162(19) -0.013(2) C33 0.035(2) 0.042(3) 0.069(3) -0.016(2) -0.017(2) 0.0015(19) C23 0.040(2) 0.035(2) 0.074(3) -0.018(2) -0.023(2) -0.0054(19) C30 0.031(2) 0.071(3) 0.072(3) -0.012(3) -0.018(2) -0.012(2) C29 0.043(3) 0.061(3) 0.077(3) -0.005(3) -0.023(2) -0.021(2) C31 0.034(2) 0.056(3) 0.071(3) -0.017(2) -0.023(2) -0.002(2) C44 0.051(3) 0.054(3) 0.062(3) -0.010(2) -0.022(2) -0.017(2) C42 0.057(3) 0.063(4) 0.091(4) -0.043(3) -0.035(3) -0.004(3) C43 0.051(3) 0.053(3) 0.095(4) -0.019(3) -0.023(3) -0.023(2) C40 0.086(4) 0.061(3) 0.062(3) -0.015(3) -0.028(3) -0.030(3) C41 0.115(5) 0.075(4) 0.072(4) -0.024(3) -0.043(3) -0.026(4) S2 0.0578(8) 0.0591(9) 0.0907(10) -0.0316(7) -0.0328(7) -0.0065(6) C3 0.039(2) 0.045(3) 0.064(3) -0.019(2) -0.015(2) 0.002(2) C14 0.039(2) 0.041(3) 0.050(3) -0.013(2) -0.0158(19) -0.0001(19) C17 0.036(2) 0.048(3) 0.045(2) -0.014(2) -0.0147(19) 0.002(2) C5 0.042(2) 0.043(3) 0.054(3) -0.005(2) -0.018(2) -0.007(2) C15 0.038(2) 0.048(3) 0.065(3) -0.013(2) -0.023(2) -0.001(2) C4 0.042(2) 0.042(3) 0.053(3) -0.008(2) -0.021(2) -0.004(2) C2 0.038(2) 0.048(3) 0.066(3) -0.021(2) -0.020(2) 0.000(2) O1 0.093(3) 0.093(3) 0.082(3) -0.014(2) -0.043(2) -0.005(2) C13 0.039(2) 0.040(3) 0.050(3) -0.007(2) -0.0188(19) -0.0017(19) C18 0.054(3) 0.048(3) 0.061(3) -0.010(2) -0.014(2) 0.001(2) O2 0.085(3) 0.066(2) 0.149(4) -0.036(2) -0.039(2) -0.023(2) C10 0.047(3) 0.057(3) 0.061(3) -0.012(2) -0.023(2) -0.009(2) C1 0.046(3) 0.067(3) 0.101(4) -0.039(3) -0.028(3) 0.003(2) C16 0.046(3) 0.062(3) 0.083(3) -0.025(3) -0.025(2) -0.006(2) C12 0.044(3) 0.055(3) 0.061(3) -0.023(2) -0.018(2) -0.002(2) C7 0.041(3) 0.079(4) 0.073(3) -0.010(3) -0.016(2) -0.010(3) C11 0.053(3) 0.063(3) 0.071(3) -0.027(3) -0.026(2) -0.009(2) C19 0.068(3) 0.047(3) 0.077(4) -0.015(3) -0.020(3) 0.016(3) C6 0.035(2) 0.061(3) 0.063(3) -0.011(2) -0.018(2) -0.006(2) C9 0.059(3) 0.072(3) 0.089(4) -0.022(3) -0.034(3) -0.018(3) C21 0.046(3) 0.075(4) 0.067(3) -0.020(3) -0.009(2) -0.013(3) C8 0.044(3) 0.090(4) 0.094(4) -0.013(3) -0.028(3) -0.017(3) C20 0.048(3) 0.073(4) 0.070(3) -0.025(3) -0.016(3) 0.006(3) C22 0.048(3) 0.054(3) 0.062(3) -0.007(2) -0.017(2) -0.002(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 O4 1.431(3) . ? S1 O3 1.445(3) . ? S1 C23 1.776(4) . ? S1 C38 1.782(4) . ? C37 C36 1.380(5) . ? C37 C24 1.401(5) . ? C37 C38 1.514(5) . ? C24 C25 1.373(5) . ? C24 C23 1.511(5) . ? C32 C27 1.412(5) . ? C32 C31 1.417(5) . ? C32 C33 1.432(6) . ? C26 C25 1.403(5) . ? C26 C35 1.410(5) . ? C26 C27 1.465(5) . ? C35 C36 1.427(5) . ? C35 C34 1.437(5) . ? C36 C39 1.504(5) . ? C39 C44 1.369(5) . ? C39 C40 1.371(6) . ? C27 C28 1.403(5) . ? C34 C33 1.349(5) . ? C28 C29 1.378(5) . ? C30 C31 1.356(6) . ? C30 C29 1.400(6) . ? C44 C43 1.393(6) . ? C42 C43 1.355(7) . ? C42 C41 1.361(7) . ? C40 C41 1.375(7) . ? S2 O2 1.425(4) . ? S2 O1 1.440(4) . ? S2 C16 1.777(5) . ? S2 C1 1.790(5) . ? C3 C2 1.359(6) . ? C3 C4 1.404(6) . ? C14 C15 1.376(6) . ? C14 C13 1.427(6) . ? C14 C17 1.490(5) . ? C17 C22 1.379(6) . ? C17 C18 1.384(6) . ? C5 C6 1.414(6) . ? C5 C10 1.411(6) . ? C5 C4 1.458(6) . ? C15 C2 1.409(5) . ? C15 C16 1.512(6) . ? C4 C13 1.422(5) . ? C2 C1 1.511(6) . ? C13 C12 1.434(6) . ? C18 C19 1.382(6) . ? C10 C9 1.406(6) . ? C10 C11 1.419(6) . ? C12 C11 1.346(6) . ? C7 C6 1.376(6) . ? C7 C8 1.393(7) . ? C19 C20 1.379(7) . ? C9 C8 1.369(6) . ? C21 C20 1.354(6) . ? C21 C22 1.386(6) . ? 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 O4 S1 O3 117.1(2) . . ? O4 S1 C23 109.3(2) . . ? O3 S1 C23 112.63(19) . . ? O4 S1 C38 109.3(2) . . ? O3 S1 C38 110.7(2) . . ? C23 S1 C38 95.68(18) . . ? C36 C37 C24 121.1(3) . . ? C36 C37 C38 125.1(4) . . ? C24 C37 C38 113.8(3) . . ? C25 C24 C37 120.4(3) . . ? C25 C24 C23 125.1(3) . . ? C37 C24 C23 114.5(3) . . ? C27 C32 C31 119.3(4) . . ? C27 C32 C33 120.0(3) . . ? C31 C32 C33 120.7(4) . . ? C25 C26 C35 119.3(3) . . ? C25 C26 C27 121.5(4) . . ? C35 C26 C27 119.2(3) . . ? C26 C35 C36 119.9(3) . . ? C26 C35 C34 119.5(3) . . ? C36 C35 C34 120.6(4) . . ? C37 C36 C35 118.6(4) . . ? C37 C36 C39 118.8(3) . . ? C35 C36 C39 122.6(3) . . ? C44 C39 C40 118.3(4) . . ? C44 C39 C36 121.8(4) . . ? C40 C39 C36 119.8(4) . . ? C37 C38 S1 103.7(3) . . ? C28 C27 C32 118.5(3) . . ? C28 C27 C26 122.8(4) . . ? C32 C27 C26 118.7(4) . . ? C33 C34 C35 121.2(4) . . ? C24 C25 C26 120.4(4) . . ? C29 C28 C27 121.1(4) . . ? C34 C33 C32 121.0(4) . . ? C24 C23 S1 103.6(3) . . ? C31 C30 C29 120.4(4) . . ? C28 C29 C30 119.9(4) . . ? C30 C31 C32 120.7(4) . . ? C39 C44 C43 120.4(4) . . ? C43 C42 C41 119.2(5) . . ? C42 C43 C44 120.5(5) . . ? C39 C40 C41 120.8(5) . . ? C42 C41 C40 120.8(5) . . ? O2 S2 O1 118.0(2) . . ? O2 S2 C16 110.9(2) . . ? O1 S2 C16 108.7(2) . . ? O2 S2 C1 111.5(2) . . ? O1 S2 C1 108.8(3) . . ? C16 S2 C1 96.9(2) . . ? C2 C3 C4 121.0(4) . . ? C15 C14 C13 118.3(4) . . ? C15 C14 C17 120.6(4) . . ? C13 C14 C17 121.1(4) . . ? C22 C17 C18 118.0(4) . . ? C22 C17 C14 122.1(4) . . ? C18 C17 C14 119.9(4) . . ? C6 C5 C10 118.0(4) . . ? C6 C5 C4 122.7(4) . . ? C10 C5 C4 119.3(4) . . ? C14 C15 C2 120.9(4) . . ? C14 C15 C16 124.1(4) . . ? C2 C15 C16 115.0(4) . . ? C3 C4 C13 118.2(4) . . ? C3 C4 C5 122.7(4) . . ? C13 C4 C5 119.1(4) . . ? C3 C2 C15 120.8(4) . . ? C3 C2 C1 124.8(4) . . ? C15 C2 C1 114.4(4) . . ? C4 C13 C14 120.6(4) . . ? C4 C13 C12 118.7(4) . . ? C14 C13 C12 120.7(4) . . ? C19 C18 C17 120.2(4) . . ? C5 C10 C9 119.4(4) . . ? C5 C10 C11 119.4(4) . . ? C9 C10 C11 121.2(4) . . ? C2 C1 S2 105.3(3) . . ? C15 C16 S2 105.3(3) . . ? C11 C12 C13 121.5(4) . . ? C6 C7 C8 120.5(4) . . ? C12 C11 C10 121.7(4) . . ? C18 C19 C20 120.7(5) . . ? C7 C6 C5 121.2(4) . . ? C8 C9 C10 121.5(5) . . ? C20 C21 C22 119.9(5) . . ? C9 C8 C7 119.5(5) . . ? C21 C20 C19 119.6(4) . . ? C17 C22 C21 121.5(4) . . ? _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 25.06 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.396 _refine_diff_density_min -0.366 _refine_diff_density_rms 0.068 _database_code_depnum_ccdc_archive 'CCDC 938978'