data_cn03 _audit_update_record ; 2007-05-29 # Formatted by publCIF ; _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C24 H22 O4 S2' _chemical_formula_weight 438.54 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 Monoclinic _symmetry_space_group_name_H-M P21/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 10.3264(9) _cell_length_b 5.9833(5) _cell_length_c 16.6810(15) _cell_angle_alpha 90.00 _cell_angle_beta 92.386(2) _cell_angle_gamma 90.00 _cell_volume 1029.76(16) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 50 _cell_measurement_theta_min 2.0 _cell_measurement_theta_max 28.0 _exptl_crystal_description needles _exptl_crystal_colour yellow _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.09 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.414 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 460 _exptl_absorpt_coefficient_mu 0.288 _exptl_absorpt_correction_type integration _exptl_absorpt_correction_T_min 0.9651 _exptl_absorpt_correction_T_max 0.9839 _exptl_absorpt_process_details 'based on measured indexed crystal faces, Bruker SHELXTL v6.12 (Bruker 1998)' _diffrn_ambient_temperature 173(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 'SMART CCD area detector' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 1 _diffrn_reflns_number 6696 _diffrn_reflns_av_R_equivalents 0.0347 _diffrn_reflns_av_sigmaI/netI 0.0327 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.97 _diffrn_reflns_theta_max 27.49 _reflns_number_total 2360 _reflns_number_gt 2014 _reflns_threshold_expression 'I>2\s(I)' _computing_data_collection 'Bruker SMART v5.624 (Bruker 1998)' _computing_cell_refinement 'Bruker SMART v5.624 & SAINT 6.36a (Bruker 1998)' _computing_data_reduction 'Bruker SHELXTL v6.14 (Bruker 2000)' _computing_structure_solution 'Bruker SHELXTL v6.14' _computing_structure_refinement 'Bruker SHELXTL v6.14' _computing_molecular_graphics 'Bruker SHELXTL v6.14' _computing_publication_material 'Bruker SHELXTL v6.14' _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^)+(0.0443P)^2^+0.3249P] 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 2360 _refine_ls_number_parameters 138 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0478 _refine_ls_R_factor_gt 0.0373 _refine_ls_wR_factor_ref 0.0940 _refine_ls_wR_factor_gt 0.0897 _refine_ls_goodness_of_fit_ref 1.075 _refine_ls_restrained_S_all 1.075 _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 0.08180(4) 0.22164(7) 0.43427(2) 0.02464(13) Uani 1 1 d . . . O1 O 0.67772(11) -0.0099(2) 0.38907(7) 0.0339(3) Uani 1 1 d . . . O2 O 0.15240(11) -0.0541(2) 0.31183(7) 0.0315(3) Uani 1 1 d . . . C1 C 0.06291(15) 0.4712(3) 0.48476(9) 0.0236(3) Uani 1 1 d . . . C2 C 0.17670(16) 0.5893(3) 0.48858(10) 0.0280(4) Uani 1 1 d . . . H2A H 0.1855 0.7325 0.5128 0.034 Uiso 1 1 calc R . . C3 C 0.27961(16) 0.4759(3) 0.45277(10) 0.0270(4) Uani 1 1 d . . . H3A H 0.3648 0.5351 0.4512 0.032 Uiso 1 1 calc R . . C4 C 0.24502(15) 0.2723(3) 0.42038(9) 0.0233(3) Uani 1 1 d . . . C5 C 0.33078(15) 0.1093(3) 0.38296(9) 0.0224(3) Uani 1 1 d . . . C6 C 0.46414(15) 0.1144(3) 0.40127(10) 0.0258(3) Uani 1 1 d . . . H6A H 0.4980 0.2231 0.4380 0.031 Uiso 1 1 calc R . . C7 C 0.54814(15) -0.0356(3) 0.36709(10) 0.0258(4) Uani 1 1 d . . . C8 C 0.50089(16) -0.1956(3) 0.31388(10) 0.0278(4) Uani 1 1 d . . . H8A H 0.5581 -0.2994 0.2907 0.033 Uiso 1 1 calc R . . C9 C 0.36832(16) -0.2030(3) 0.29454(10) 0.0279(4) Uani 1 1 d . . . H9A H 0.3355 -0.3118 0.2575 0.033 Uiso 1 1 calc R . . C10 C 0.28411(15) -0.0545(3) 0.32843(10) 0.0241(3) Uani 1 1 d . . . C11 C 0.76430(17) -0.1731(3) 0.35961(11) 0.0344(4) Uani 1 1 d . . . H11C H 0.7383 -0.3218 0.3775 0.052 Uiso 1 1 calc R . . H11B H 0.8526 -0.1411 0.3802 0.052 Uiso 1 1 calc R . . H11A H 0.7615 -0.1686 0.3008 0.052 Uiso 1 1 calc R . . C12 C 0.09969(18) -0.2413(3) 0.26868(13) 0.0386(5) Uani 1 1 d . . . H12C H 0.1329 -0.2432 0.2145 0.058 Uiso 1 1 calc R . . H12B H 0.0050 -0.2298 0.2652 0.058 Uiso 1 1 calc R . . H12A H 0.1250 -0.3795 0.2967 0.058 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S1 0.0214(2) 0.0251(2) 0.0276(2) -0.00564(16) 0.00349(15) 0.00160(15) O1 0.0217(6) 0.0439(8) 0.0359(7) -0.0066(6) 0.0001(5) 0.0053(5) O2 0.0212(6) 0.0328(7) 0.0404(7) -0.0136(5) 0.0004(5) 0.0015(5) C1 0.0273(8) 0.0221(8) 0.0216(8) -0.0015(6) 0.0023(6) 0.0046(6) C2 0.0304(9) 0.0230(8) 0.0307(9) -0.0045(7) 0.0041(7) 0.0018(7) C3 0.0252(8) 0.0265(9) 0.0297(9) -0.0009(7) 0.0039(7) -0.0006(6) C4 0.0229(7) 0.0251(8) 0.0220(8) 0.0006(6) 0.0030(6) 0.0015(6) C5 0.0234(8) 0.0239(8) 0.0202(7) 0.0007(6) 0.0046(6) 0.0013(6) C6 0.0262(8) 0.0291(9) 0.0222(8) -0.0029(7) 0.0016(6) -0.0001(7) C7 0.0208(8) 0.0320(9) 0.0246(8) 0.0031(7) 0.0022(6) 0.0021(6) C8 0.0248(8) 0.0280(9) 0.0312(9) -0.0028(7) 0.0074(7) 0.0036(6) C9 0.0265(8) 0.0271(9) 0.0304(9) -0.0070(7) 0.0051(7) -0.0016(7) C10 0.0217(8) 0.0262(8) 0.0246(8) -0.0005(6) 0.0039(6) 0.0002(6) C11 0.0242(9) 0.0428(11) 0.0366(10) 0.0029(8) 0.0039(7) 0.0086(7) C12 0.0263(9) 0.0398(11) 0.0494(12) -0.0169(9) -0.0015(8) -0.0022(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 C1 1.7296(16) . ? S1 C4 1.7375(17) . ? O1 C7 1.3812(19) . ? O1 C11 1.425(2) . ? O2 C10 1.3767(19) . ? O2 C12 1.427(2) . ? C1 C2 1.370(2) . ? C1 C1 1.456(3) 3_566 ? C2 C3 1.414(2) . ? C3 C4 1.374(2) . ? C4 C5 1.473(2) . ? C5 C6 1.399(2) . ? C5 C10 1.409(2) . ? C6 C7 1.387(2) . ? C7 C8 1.381(2) . ? C8 C9 1.394(2) . ? C9 C10 1.381(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 C1 S1 C4 92.52(8) . . ? C7 O1 C11 116.54(14) . . ? C10 O2 C12 116.93(13) . . ? C2 C1 C1 129.65(19) . 3_566 ? C2 C1 S1 110.72(12) . . ? C1 C1 S1 119.63(16) 3_566 . ? C1 C2 C3 113.04(15) . . ? C4 C3 C2 113.82(15) . . ? C3 C4 C5 127.04(15) . . ? C3 C4 S1 109.87(12) . . ? C5 C4 S1 123.00(12) . . ? C6 C5 C10 117.61(15) . . ? C6 C5 C4 119.80(15) . . ? C10 C5 C4 122.59(15) . . ? C7 C6 C5 121.54(16) . . ? C8 C7 O1 124.08(15) . . ? C8 C7 C6 120.17(15) . . ? O1 C7 C6 115.74(15) . . ? C7 C8 C9 119.22(16) . . ? C10 C9 C8 120.92(16) . . ? O2 C10 C9 123.54(15) . . ? O2 C10 C5 115.93(14) . . ? C9 C10 C5 120.53(15) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.369 _refine_diff_density_min -0.185 _refine_diff_density_rms 0.048