# Supplementary Material (ESI) for New Journal of Chemistry # This journal is (c) The Royal Society of Chemistry and # The Centre National de la Recherche Scientifique, 2009 data_global _journal_coden_Cambridge 440 _journal_volume ? _journal_page_first ? _journal_year ? loop_ _publ_author_name 'Paola Paoli' 'Maria Altamura' 'Valentina Fedi' 'Danilo Giannotti' 'Patrizia Rossi' _publ_contact_author_name 'Paola Paoli' _publ_contact_author_email paolapaoli@unifi.it _publ_section_title ; Privileged structures: synthesis and structural investigations on tricyclic sulfonamides ; # Attachment '- 4a-8b-13a-14a-5bme2so4-15ame2so4.cif' data_4a _database_code_depnum_ccdc_archive 'CCDC 745476' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H9 N O3 S' _chemical_formula_weight 247.26 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 orthorhombic _symmetry_space_group_name_H-M Pna21 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' '-x+1/2, y+1/2, z+1/2' 'x+1/2, -y+1/2, z' _cell_length_a 8.3420(10) _cell_length_b 9.678(2) _cell_length_c 13.675(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1104.0(3) _cell_formula_units_Z 4 _cell_measurement_temperature 298 _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.6 _exptl_crystal_size_mid 0.54 _exptl_crystal_size_min 0.48 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.488 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 512 _exptl_absorpt_coefficient_mu 0.287 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.847 _exptl_absorpt_correction_T_max 0.867 _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.29.2 (release 20-01-2006 CrysAlis171 .NET) (compiled Jan 20 2006,12:36:28) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 298 _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Xcalibur3 4 circles diffractometer' _diffrn_measurement_method 'intensity from \w scans' _diffrn_detector_area_resol_mean 16.4547 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6149 _diffrn_reflns_av_R_equivalents 0.0386 _diffrn_reflns_av_sigmaI/netI 0.0714 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 4.21 _diffrn_reflns_theta_max 28.35 _reflns_number_total 2174 _reflns_number_gt 1143 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlis CCD, Oxford Diffraction Ltd., Version 1.171.29.2 (release 20-01-2006 CrysAlis171 .NET) (compiled Jan 20 2006,12:36:28) ; _computing_cell_refinement ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.29.2 (release 20-01-2006 CrysAlis171 .NET) (compiled Jan 20 2006,12:36:28) ; _computing_data_reduction ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.29.2 (release 20-01-2006 CrysAlis171 .NET) (compiled Jan 20 2006,12:36:28) ; _computing_structure_solution 'SIR97 (Altomare, 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-3 (Farruggia, 1997)' _computing_publication_material 'PARST97 (Nardelli, 1995)' _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^)+(0.0306P)^2^+0.0000P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.07(8) _refine_ls_number_reflns 2174 _refine_ls_number_parameters 190 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0712 _refine_ls_R_factor_gt 0.0354 _refine_ls_wR_factor_ref 0.0698 _refine_ls_wR_factor_gt 0.0629 _refine_ls_goodness_of_fit_ref 0.820 _refine_ls_restrained_S_all 0.820 _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 0.41831(10) 1.12382(9) 1.37636(6) 0.0537(2) Uani 1 1 d . . . O1 O 0.3273(3) 1.1341(2) 1.46434(13) 0.0682(7) Uani 1 1 d . . . O2 O 0.5888(2) 1.1072(2) 1.3822(2) 0.0636(6) Uani 1 1 d . . . O3 O 0.5292(2) 1.0507(2) 1.17917(17) 0.0597(6) Uani 1 1 d . . . N1 N 0.3795(3) 1.2604(3) 1.31255(18) 0.0557(8) Uani 1 1 d . . . C1 C 0.3432(3) 0.9875(3) 1.3053(2) 0.0451(7) Uani 1 1 d . . . C2 C 0.4031(4) 0.9711(3) 1.2114(2) 0.0457(8) Uani 1 1 d . . . C4 C 0.2373(5) 0.7726(4) 1.1916(3) 0.0598(9) Uani 1 1 d . . . C3 C 0.3481(4) 0.8642(4) 1.1547(3) 0.0555(9) Uani 1 1 d . . . C5 C 0.1770(5) 0.7890(4) 1.2840(3) 0.0649(11) Uani 1 1 d . . . C6 C 0.2296(4) 0.8981(4) 1.3402(3) 0.0588(10) Uani 1 1 d . . . C7 C 0.4417(4) 1.2882(3) 1.2180(2) 0.0465(8) Uani 1 1 d . . . C8 C 0.5092(3) 1.1916(4) 1.1578(2) 0.0465(8) Uani 1 1 d . . . C9 C 0.5721(4) 1.2297(5) 1.0674(3) 0.0591(10) Uani 1 1 d . . . C10 C 0.5665(4) 1.3660(5) 1.0365(3) 0.0685(10) Uani 1 1 d . . . C11 C 0.4957(5) 1.4610(5) 1.0969(3) 0.0732(12) Uani 1 1 d . . . C12 C 0.4337(4) 1.4246(4) 1.1864(3) 0.0607(10) Uani 1 1 d . . . HN1 H 0.296(5) 1.317(4) 1.335(3) 0.106(15) Uiso 1 1 d . . . H3 H 0.394(4) 0.862(3) 1.094(2) 0.054(10) Uiso 1 1 d . . . H4 H 0.201(4) 0.693(4) 1.151(2) 0.068(11) Uiso 1 1 d . . . H5 H 0.113(4) 0.727(3) 1.313(2) 0.060(11) Uiso 1 1 d . . . H6 H 0.198(3) 0.914(3) 1.398(2) 0.035(9) Uiso 1 1 d . . . H9 H 0.608(3) 1.167(3) 1.029(2) 0.048(11) Uiso 1 1 d . . . H10 H 0.644(5) 1.400(4) 0.964(3) 0.116(13) Uiso 1 1 d . . . H11 H 0.483(4) 1.552(4) 1.079(2) 0.058(10) Uiso 1 1 d . . . H12 H 0.396(4) 1.500(4) 1.232(3) 0.088(12) 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 0.0511(5) 0.0651(6) 0.0451(4) -0.0023(5) -0.0007(5) -0.0020(4) O1 0.0776(15) 0.0865(18) 0.0406(13) -0.0089(12) 0.0081(12) -0.0076(13) O2 0.0463(12) 0.0786(16) 0.0659(12) 0.0040(14) -0.0110(12) -0.0070(12) O3 0.0569(13) 0.0514(15) 0.0710(15) 0.0072(12) 0.0195(12) 0.0046(12) N1 0.0711(19) 0.0504(18) 0.0457(17) 0.0002(14) 0.0085(15) 0.0092(16) C1 0.0415(17) 0.049(2) 0.0445(18) 0.0019(16) 0.0011(16) 0.0000(16) C2 0.0449(18) 0.047(2) 0.045(2) -0.0008(17) 0.0046(16) 0.0045(16) C4 0.065(2) 0.056(3) 0.058(2) -0.003(2) -0.007(2) 0.000(2) C3 0.053(2) 0.063(3) 0.050(2) 0.001(2) 0.0057(19) 0.010(2) C5 0.058(2) 0.075(3) 0.062(3) 0.006(2) -0.008(2) -0.018(2) C6 0.052(2) 0.080(3) 0.045(2) -0.005(2) 0.0008(19) -0.004(2) C7 0.0485(19) 0.048(2) 0.0430(18) -0.0029(18) -0.0043(16) 0.0051(17) C8 0.0357(18) 0.054(2) 0.049(2) 0.0049(18) 0.0005(16) -0.0031(16) C9 0.055(2) 0.070(3) 0.053(2) 0.002(2) 0.000(2) 0.000(2) C10 0.065(2) 0.081(3) 0.060(2) 0.018(2) -0.0044(19) -0.009(2) C11 0.078(3) 0.057(3) 0.084(3) 0.015(3) -0.019(2) 0.003(3) C12 0.062(2) 0.060(3) 0.060(2) 0.000(2) -0.008(2) -0.001(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 O1 1.426(2) . ? S1 O2 1.4339(19) . ? S1 N1 1.616(3) . ? S1 C1 1.754(3) . ? O3 C2 1.377(3) . ? O3 C8 1.405(4) . ? N1 C7 1.420(4) . ? C1 C6 1.370(4) . ? C1 C2 1.386(4) . ? C2 C3 1.373(4) . ? C4 C5 1.368(5) . ? C4 C3 1.376(5) . ? C5 C6 1.378(5) . ? C7 C8 1.367(4) . ? C7 C12 1.390(5) . ? C8 C9 1.392(5) . ? C9 C10 1.386(5) . ? C10 C11 1.370(6) . ? C11 C12 1.375(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 O1 S1 O2 119.28(15) . . ? O1 S1 N1 106.98(15) . . ? O2 S1 N1 108.69(15) . . ? O1 S1 C1 109.24(15) . . ? O2 S1 C1 107.49(15) . . ? N1 S1 C1 104.13(14) . . ? C2 O3 C8 121.3(2) . . ? C7 N1 S1 125.0(3) . . ? C6 C1 C2 120.0(3) . . ? C6 C1 S1 121.9(3) . . ? C2 C1 S1 118.1(3) . . ? C3 C2 O3 119.7(3) . . ? C3 C2 C1 119.3(3) . . ? O3 C2 C1 120.5(3) . . ? C5 C4 C3 120.7(4) . . ? C2 C3 C4 120.1(4) . . ? C4 C5 C6 119.2(4) . . ? C1 C6 C5 120.6(4) . . ? C8 C7 C12 118.8(3) . . ? C8 C7 N1 124.7(3) . . ? C12 C7 N1 116.5(3) . . ? C7 C8 C9 120.5(3) . . ? C7 C8 O3 126.0(3) . . ? C9 C8 O3 113.4(3) . . ? C10 C9 C8 120.7(4) . . ? C11 C10 C9 118.0(4) . . ? C10 C11 C12 121.8(4) . . ? C11 C12 C7 120.1(4) . . ? _diffrn_measured_fraction_theta_max 0.919 _diffrn_reflns_theta_full 28.35 _diffrn_measured_fraction_theta_full 0.919 _refine_diff_density_max 0.241 _refine_diff_density_min -0.147 _refine_diff_density_rms 0.037 #===END data_8b _database_code_depnum_ccdc_archive 'CCDC 745477' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H9 Br N2 O2 S' _chemical_formula_weight 325.18 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' Br Br -0.2901 2.4595 '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 7.3326(15) _cell_length_b 8.131(3) _cell_length_c 10.314(2) _cell_angle_alpha 97.41(2) _cell_angle_beta 90.145(17) _cell_angle_gamma 91.61(2) _cell_volume 609.5(3) _cell_formula_units_Z 2 _cell_measurement_temperature 298 _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.772 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 324 _exptl_absorpt_coefficient_mu 3.537 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.222 _exptl_absorpt_correction_T_max 0.322 _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.29.2 (release 20-01-2006 CrysAlis171 .NET) (compiled Jan 20 2006,12:36:28) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 298 _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Xcalibur3 4 circles diffractometer' _diffrn_measurement_method 'intensity from \w scans' _diffrn_detector_area_resol_mean 16.4547 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 2963 _diffrn_reflns_av_R_equivalents 0.0205 _diffrn_reflns_av_sigmaI/netI 0.0393 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -4 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 4.35 _diffrn_reflns_theta_max 31.88 _reflns_number_total 2394 _reflns_number_gt 1481 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlis CCD, Oxford Diffraction Ltd., Version 1.171.29.2 (release 20-01-2006 CrysAlis171 .NET) (compiled Jan 20 2006,12:36:28) ; _computing_cell_refinement ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.29.2 (release 20-01-2006 CrysAlis171 .NET) (compiled Jan 20 2006,12:36:28) ; _computing_data_reduction ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.29.2 (release 20-01-2006 CrysAlis171 .NET) (compiled Jan 20 2006,12:36:28) ; _computing_structure_solution 'SIR97 (Altomare, 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-3 (Farruggia, 1997)' _computing_publication_material 'PARST97 (Nardelli, 1995)' _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^)+(0.0783P)^2^+0.0000P] 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 2394 _refine_ls_number_parameters 199 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0690 _refine_ls_R_factor_gt 0.0441 _refine_ls_wR_factor_ref 0.1309 _refine_ls_wR_factor_gt 0.1141 _refine_ls_goodness_of_fit_ref 0.978 _refine_ls_restrained_S_all 0.978 _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 0.85248(11) 0.74344(12) 1.03060(9) 0.0352(3) Uani 1 1 d . . . Br1 Br 0.09968(6) 0.78942(8) 0.60305(5) 0.0813(3) Uani 1 1 d . . . O1 O 1.0256(3) 0.8115(3) 1.0798(3) 0.0457(7) Uani 1 1 d . . . O2 O 0.8480(3) 0.5968(3) 0.9384(2) 0.0402(6) Uani 1 1 d . . . N1 N 0.7526(5) 0.8867(5) 0.9682(3) 0.0377(9) Uani 1 1 d . . . N2 N 0.4254(4) 0.6915(5) 1.0307(3) 0.0380(8) Uani 1 1 d . . . C1 C 0.7134(5) 0.7073(5) 1.1623(3) 0.0350(8) Uani 1 1 d . . . C2 C 0.5235(5) 0.6851(4) 1.1446(3) 0.0331(8) Uani 1 1 d . . . C3 C 0.4242(5) 0.6479(5) 1.2531(4) 0.0411(9) Uani 1 1 d . . . C4 C 0.5059(6) 0.6377(6) 1.3712(4) 0.0518(11) Uani 1 1 d . . . C5 C 0.6925(6) 0.6640(6) 1.3878(4) 0.0582(12) Uani 1 1 d . . . C6 C 0.7945(6) 0.7000(6) 1.2827(4) 0.0488(10) Uani 1 1 d . . . C7 C 0.6026(5) 0.8526(4) 0.8818(3) 0.0337(8) Uani 1 1 d . . . C8 C 0.4511(4) 0.7606(4) 0.9147(3) 0.0305(8) Uani 1 1 d . . . C9 C 0.3033(5) 0.7379(5) 0.8263(3) 0.0394(9) Uani 1 1 d . . . C10 C 0.3073(5) 0.8094(6) 0.7141(4) 0.0479(11) Uani 1 1 d . . . C11 C 0.4590(6) 0.9021(6) 0.6803(4) 0.0529(11) Uani 1 1 d . . . C12 C 0.6066(6) 0.9200(6) 0.7645(4) 0.0473(10) Uani 1 1 d . . . HN2 H 0.327(5) 0.643(5) 1.033(3) 0.029(10) Uiso 1 1 d . . . H3 H 0.297(5) 0.636(5) 1.247(3) 0.040(10) Uiso 1 1 d . . . H4 H 0.431(5) 0.605(5) 1.436(4) 0.033(9) Uiso 1 1 d . . . H5 H 0.742(7) 0.658(6) 1.476(5) 0.083(15) Uiso 1 1 d . . . H6 H 0.920(6) 0.719(5) 1.295(3) 0.036(9) Uiso 1 1 d . . . H9 H 0.201(6) 0.670(6) 0.848(4) 0.057(13) Uiso 1 1 d . . . H12 H 0.712(7) 0.991(7) 0.752(5) 0.071(15) Uiso 1 1 d . . . H11 H 0.465(5) 0.955(5) 0.606(4) 0.037(10) Uiso 1 1 d . . . H1N H 0.791(5) 0.962(5) 0.974(3) 0.017(11) 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 0.0235(4) 0.0356(6) 0.0475(5) 0.0092(4) -0.0035(3) -0.0016(4) Br1 0.0571(3) 0.1267(6) 0.0616(3) 0.0180(3) -0.0250(2) 0.0068(3) O1 0.0264(12) 0.0484(18) 0.0638(16) 0.0146(13) -0.0060(11) -0.0069(13) O2 0.0337(13) 0.0335(15) 0.0527(15) 0.0035(12) 0.0011(10) 0.0005(12) N1 0.0331(18) 0.022(2) 0.058(2) 0.0096(16) -0.0071(14) -0.0093(19) N2 0.0226(14) 0.048(2) 0.0444(17) 0.0140(15) -0.0044(12) -0.0109(17) C1 0.0292(17) 0.031(2) 0.0441(19) 0.0055(15) -0.0037(14) -0.0030(17) C2 0.0323(17) 0.027(2) 0.0394(17) 0.0029(14) -0.0029(13) -0.0016(17) C3 0.0340(19) 0.045(3) 0.045(2) 0.0112(17) 0.0009(15) 0.0012(19) C4 0.050(2) 0.065(3) 0.043(2) 0.015(2) 0.0026(18) -0.006(2) C5 0.057(3) 0.081(4) 0.038(2) 0.017(2) -0.0107(19) -0.004(3) C6 0.035(2) 0.060(3) 0.051(2) 0.010(2) -0.0113(17) -0.005(2) C7 0.0317(18) 0.024(2) 0.0455(19) 0.0044(15) -0.0032(14) 0.0008(17) C8 0.0280(16) 0.024(2) 0.0388(17) 0.0032(14) -0.0017(13) 0.0012(16) C9 0.0330(19) 0.046(3) 0.0394(19) 0.0042(17) -0.0026(14) 0.005(2) C10 0.040(2) 0.060(3) 0.043(2) 0.0019(18) -0.0077(16) 0.010(2) C11 0.055(3) 0.060(3) 0.047(2) 0.020(2) 0.0010(19) 0.005(2) C12 0.043(2) 0.049(3) 0.052(2) 0.015(2) 0.0021(17) 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 O2 1.426(3) . ? S1 O1 1.435(3) . ? S1 N1 1.596(3) . ? S1 C1 1.750(4) . ? Br1 C10 1.893(4) . ? N1 C7 1.412(5) . ? N2 C2 1.383(4) . ? N2 C8 1.398(5) . ? C1 C6 1.385(5) . ? C1 C2 1.407(5) . ? C2 C3 1.397(5) . ? C3 C4 1.370(5) . ? C4 C5 1.386(6) . ? C5 C6 1.376(6) . ? C7 C8 1.389(5) . ? C7 C12 1.391(5) . ? C8 C9 1.407(5) . ? C9 C10 1.361(6) . ? C10 C11 1.397(6) . ? C11 C12 1.379(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 O2 S1 O1 118.99(15) . . ? O2 S1 N1 108.82(18) . . ? O1 S1 N1 107.0(2) . . ? O2 S1 C1 108.02(17) . . ? O1 S1 C1 109.10(16) . . ? N1 S1 C1 103.85(17) . . ? C7 N1 S1 122.0(3) . . ? C2 N2 C8 136.5(3) . . ? C6 C1 C2 121.2(3) . . ? C6 C1 S1 118.6(3) . . ? C2 C1 S1 120.2(3) . . ? N2 C2 C3 116.6(3) . . ? N2 C2 C1 127.1(3) . . ? C3 C2 C1 116.3(3) . . ? C4 C3 C2 122.1(4) . . ? C3 C4 C5 120.8(4) . . ? C6 C5 C4 118.6(4) . . ? C5 C6 C1 120.9(4) . . ? C8 C7 C12 120.4(4) . . ? C8 C7 N1 121.3(3) . . ? C12 C7 N1 118.2(4) . . ? C7 C8 N2 126.6(3) . . ? C7 C8 C9 118.2(3) . . ? N2 C8 C9 115.1(4) . . ? C10 C9 C8 120.5(4) . . ? C9 C10 C11 121.6(4) . . ? C9 C10 Br1 119.5(3) . . ? C11 C10 Br1 118.8(3) . . ? C12 C11 C10 118.0(4) . . ? C11 C12 C7 121.1(5) . . ? _diffrn_measured_fraction_theta_max 0.572 _diffrn_reflns_theta_full 31.88 _diffrn_measured_fraction_theta_full 0.572 _refine_diff_density_max 0.538 _refine_diff_density_min -0.538 _refine_diff_density_rms 0.076 #===END data_13a _database_code_depnum_ccdc_archive 'CCDC 745478' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H9 N O2 S2' _chemical_formula_weight 263.32 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' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/a loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z' '-x, -y, -z' 'x-1/2, -y-1/2, z' _cell_length_a 7.1412(5) _cell_length_b 22.2553(18) _cell_length_c 7.9556(5) _cell_angle_alpha 90.00 _cell_angle_beta 109.175(8) _cell_angle_gamma 90.00 _cell_volume 1194.23(15) _cell_formula_units_Z 4 _cell_measurement_temperature 298 _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.58 _exptl_crystal_size_mid 0.48 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.465 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 544 _exptl_absorpt_coefficient_mu 0.433 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.795 _exptl_absorpt_correction_T_max 0.859 _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.29.2 (release 20-01-2006 CrysAlis171 .NET) (compiled Jan 20 2006,12:36:28) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 298 _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Xcalibur3 4 circles diffractometer' _diffrn_measurement_method 'intensity from \w scans' _diffrn_detector_area_resol_mean 16.4547 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8323 _diffrn_reflns_av_R_equivalents 0.0360 _diffrn_reflns_av_sigmaI/netI 0.0738 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_k_max 29 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 3.80 _diffrn_reflns_theta_max 28.42 _reflns_number_total 2569 _reflns_number_gt 1488 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlis CCD, Oxford Diffraction Ltd., Version 1.171.29.2 (release 20-01-2006 CrysAlis171 .NET) (compiled Jan 20 2006,12:36:28) ; _computing_cell_refinement ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.29.2 (release 20-01-2006 CrysAlis171 .NET) (compiled Jan 20 2006,12:36:28) ; _computing_data_reduction ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.29.2 (release 20-01-2006 CrysAlis171 .NET) (compiled Jan 20 2006,12:36:28) ; _computing_structure_solution 'SIR97 (Altomare, 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-3 (Farruggia, 1997)' _computing_publication_material 'PARST97 (Nardelli, 1995)' _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^)+(0.0371P)^2^+0.3350P] 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 2569 _refine_ls_number_parameters 190 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0972 _refine_ls_R_factor_gt 0.0428 _refine_ls_wR_factor_ref 0.1000 _refine_ls_wR_factor_gt 0.0795 _refine_ls_goodness_of_fit_ref 1.029 _refine_ls_restrained_S_all 1.029 _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 0.12283(10) 0.17750(3) 0.38946(8) 0.0459(2) Uani 1 1 d . . . S2 S -0.16385(11) 0.12959(4) 0.65638(10) 0.0639(3) Uani 1 1 d . . . O1 O 0.1417(3) 0.23898(9) 0.3443(2) 0.0685(6) Uani 1 1 d . . . O2 O 0.2312(3) 0.13200(9) 0.3344(2) 0.0624(6) Uani 1 1 d . . . N1 N -0.1092(4) 0.16155(12) 0.3052(3) 0.0481(6) Uani 1 1 d . . . C1 C 0.1984(3) 0.17417(10) 0.6244(3) 0.0370(6) Uani 1 1 d . . . C2 C 0.0876(4) 0.15297(12) 0.7280(3) 0.0426(6) Uani 1 1 d . . . C3 C 0.1757(5) 0.15403(14) 0.9116(4) 0.0541(8) Uani 1 1 d . . . C4 C 0.3652(5) 0.17439(15) 0.9911(4) 0.0611(8) Uani 1 1 d . . . C5 C 0.4740(5) 0.19435(15) 0.8890(4) 0.0639(9) Uani 1 1 d . . . C6 C 0.3912(4) 0.19420(12) 0.7056(4) 0.0483(7) Uani 1 1 d . . . C7 C -0.1719(4) 0.10104(12) 0.3186(3) 0.0474(7) Uani 1 1 d . . . C8 C -0.1951(3) 0.08062(13) 0.4741(4) 0.0519(7) Uani 1 1 d . . . C9 C -0.2610(4) 0.02215(17) 0.4815(6) 0.0680(9) Uani 1 1 d . . . C10 C -0.3013(5) -0.0145(2) 0.3349(7) 0.0858(13) Uani 1 1 d . . . C11 C -0.2728(5) 0.00556(17) 0.1827(7) 0.0851(13) Uani 1 1 d . . . C12 C -0.2091(5) 0.06335(16) 0.1739(5) 0.0659(9) Uani 1 1 d . . . H1N H -0.165(3) 0.1852(11) 0.323(3) 0.023(8) Uiso 1 1 d . . . H3 H 0.106(4) 0.1401(13) 0.979(4) 0.068(9) Uiso 1 1 d . . . H4 H 0.420(4) 0.1725(13) 1.120(4) 0.078(9) Uiso 1 1 d . . . H5 H 0.593(4) 0.2074(12) 0.933(4) 0.056(8) Uiso 1 1 d . . . H6 H 0.470(4) 0.2042(10) 0.631(3) 0.045(7) Uiso 1 1 d . . . H9 H -0.276(4) 0.0110(13) 0.592(4) 0.068(10) Uiso 1 1 d . . . H10 H -0.344(5) -0.0514(18) 0.347(4) 0.101(14) Uiso 1 1 d . . . H11 H -0.296(5) -0.0221(17) 0.086(5) 0.093(11) Uiso 1 1 d . . . H12 H -0.185(4) 0.0762(14) 0.079(4) 0.067(11) 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 0.0522(4) 0.0472(5) 0.0382(3) 0.0059(3) 0.0149(3) -0.0032(3) S2 0.0480(4) 0.0894(7) 0.0617(5) -0.0001(4) 0.0280(4) -0.0078(4) O1 0.0805(14) 0.0548(14) 0.0592(12) 0.0217(10) 0.0079(10) -0.0178(11) O2 0.0656(12) 0.0795(16) 0.0486(11) -0.0019(10) 0.0277(10) 0.0110(11) N1 0.0523(15) 0.0418(17) 0.0441(13) -0.0013(11) 0.0075(11) 0.0042(13) C1 0.0453(14) 0.0264(14) 0.0378(12) 0.0011(11) 0.0116(11) 0.0025(11) C2 0.0434(14) 0.0440(16) 0.0421(14) -0.0008(12) 0.0164(11) 0.0024(12) C3 0.065(2) 0.062(2) 0.0407(15) -0.0008(14) 0.0252(15) 0.0027(15) C4 0.069(2) 0.070(2) 0.0397(15) -0.0002(15) 0.0115(15) 0.0027(17) C5 0.0514(19) 0.067(2) 0.0582(19) -0.0008(16) -0.0023(16) -0.0100(16) C6 0.0463(16) 0.0479(19) 0.0500(16) 0.0071(13) 0.0147(13) -0.0038(12) C7 0.0413(14) 0.0356(17) 0.0548(16) -0.0023(13) 0.0018(12) 0.0004(12) C8 0.0331(14) 0.0508(19) 0.0656(18) 0.0066(15) 0.0077(12) -0.0018(13) C9 0.0462(17) 0.058(2) 0.093(3) 0.018(2) 0.0135(17) -0.0030(16) C10 0.057(2) 0.049(3) 0.137(4) 0.008(3) 0.011(2) -0.0068(18) C11 0.074(2) 0.042(2) 0.115(3) -0.028(2) -0.001(2) -0.0057(18) C12 0.065(2) 0.055(2) 0.064(2) -0.0073(18) 0.0025(17) 0.0050(16) _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 1.428(2) . ? S1 O1 1.4321(19) . ? S1 N1 1.610(3) . ? S1 C1 1.769(2) . ? S2 C8 1.769(3) . ? S2 C2 1.774(3) . ? N1 C7 1.434(4) . ? C1 C6 1.388(3) . ? C1 C2 1.399(3) . ? C2 C3 1.388(3) . ? C3 C4 1.369(4) . ? C4 C5 1.369(4) . ? C5 C6 1.382(4) . ? C7 C12 1.378(4) . ? C7 C8 1.378(4) . ? C8 C9 1.392(4) . ? C9 C10 1.374(6) . ? C10 C11 1.366(6) . ? C11 C12 1.374(5) . ? 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 119.71(13) . . ? O2 S1 N1 107.66(13) . . ? O1 S1 N1 105.97(13) . . ? O2 S1 C1 106.65(11) . . ? O1 S1 C1 106.49(11) . . ? N1 S1 C1 110.22(12) . . ? C8 S2 C2 106.61(12) . . ? C7 N1 S1 118.67(19) . . ? C6 C1 C2 120.0(2) . . ? C6 C1 S1 113.0(2) . . ? C2 C1 S1 126.99(18) . . ? C3 C2 C1 117.7(2) . . ? C3 C2 S2 113.9(2) . . ? C1 C2 S2 128.20(18) . . ? C4 C3 C2 122.0(3) . . ? C3 C4 C5 120.0(3) . . ? C4 C5 C6 119.7(3) . . ? C5 C6 C1 120.5(3) . . ? C12 C7 C8 120.1(3) . . ? C12 C7 N1 119.3(3) . . ? C8 C7 N1 120.6(2) . . ? C7 C8 C9 119.2(3) . . ? C7 C8 S2 120.9(2) . . ? C9 C8 S2 119.7(3) . . ? C10 C9 C8 119.9(4) . . ? C11 C10 C9 120.5(4) . . ? C10 C11 C12 119.9(4) . . ? C11 C12 C7 120.3(4) . . ? _diffrn_measured_fraction_theta_max 0.851 _diffrn_reflns_theta_full 28.42 _diffrn_measured_fraction_theta_full 0.851 _refine_diff_density_max 0.211 _refine_diff_density_min -0.275 _refine_diff_density_rms 0.050 #===END data_14a _database_code_depnum_ccdc_archive 'CCDC 745479' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H9 N O4 S2' _chemical_formula_weight 295.32 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 triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.050(3) _cell_length_b 8.123(3) _cell_length_c 11.287(6) _cell_angle_alpha 101.816(9) _cell_angle_beta 97.338(9) _cell_angle_gamma 119.11(2) _cell_volume 608.5(5) _cell_formula_units_Z 2 _cell_measurement_temperature 298 _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.44 _exptl_crystal_size_mid 0.38 _exptl_crystal_size_min 0.32 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.612 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 304 _exptl_absorpt_coefficient_mu 0.446 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.833 _exptl_absorpt_correction_T_max 0.859 _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.29.2 (release 20-01-2006 CrysAlis171 .NET) (compiled Jan 20 2006,12:36:28) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Xcalibur3 4 circles diffractometer' _diffrn_measurement_method 'intensity from \w scans' _diffrn_detector_area_resol_mean 16.4547 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3621 _diffrn_reflns_av_R_equivalents 0.0583 _diffrn_reflns_av_sigmaI/netI 0.3093 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 3.83 _diffrn_reflns_theta_max 25.87 _reflns_number_total 1709 _reflns_number_gt 657 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlis CCD, Oxford Diffraction Ltd., Version 1.171.29.2 (release 20-01-2006 CrysAlis171 .NET) (compiled Jan 20 2006,12:36:28) ; _computing_cell_refinement ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.29.2 (release 20-01-2006 CrysAlis171 .NET) (compiled Jan 20 2006,12:36:28) ; _computing_data_reduction ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.29.2 (release 20-01-2006 CrysAlis171 .NET) (compiled Jan 20 2006,12:36:28) ; _computing_structure_solution 'SIR97 (Altomare, 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-3 (Farruggia, 1997)' _computing_publication_material 'PARST97 (Nardelli, 1995)' _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^)+(0.0517P)^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 1709 _refine_ls_number_parameters 176 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1564 _refine_ls_R_factor_gt 0.0567 _refine_ls_wR_factor_ref 0.1189 _refine_ls_wR_factor_gt 0.1042 _refine_ls_goodness_of_fit_ref 0.792 _refine_ls_restrained_S_all 0.792 _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 0.8292(3) 1.0054(2) 0.70063(19) 0.0464(6) Uani 1 1 d . . . S2 S 0.6732(3) 0.6373(3) 0.85550(16) 0.0374(6) Uani 1 1 d . . . O1 O 1.0359(6) 1.1392(5) 0.7244(4) 0.0516(15) Uani 1 1 d . . . O2 O 0.6932(6) 1.0172(6) 0.6109(4) 0.0503(13) Uani 1 1 d . . . O3 O 0.8590(6) 0.7831(6) 0.9470(4) 0.0441(13) Uani 1 1 d . . . O4 O 0.5707(6) 0.4437(5) 0.8671(4) 0.0450(13) Uani 1 1 d . . . N1 N 0.7793(9) 1.0381(8) 0.8324(5) 0.0355(17) Uani 1 1 d . . . C1 C 0.7858(8) 0.7636(9) 0.6456(6) 0.0293(17) Uani 1 1 d . . . C2 C 0.7184(8) 0.6127(9) 0.7043(5) 0.0262(17) Uani 1 1 d . . . C3 C 0.6897(8) 0.4323(9) 0.6424(7) 0.0379(19) Uani 1 1 d . . . H3 H 0.6430 0.3312 0.6790 0.046 Uiso 1 1 calc R . . C4 C 0.7289(8) 0.3982(10) 0.5268(7) 0.043(2) Uani 1 1 d . . . H4 H 0.7080 0.2750 0.4869 0.052 Uiso 1 1 calc R . . C5 C 0.7969(9) 0.5420(11) 0.4722(6) 0.041(2) Uani 1 1 d . . . H5 H 0.8284 0.5212 0.3963 0.049 Uiso 1 1 calc R . . C6 C 0.8191(8) 0.7199(10) 0.5300(7) 0.041(2) Uani 1 1 d . . . H6 H 0.8587 0.8158 0.4890 0.050 Uiso 1 1 calc R . . C7 C 0.5760(9) 0.9140(9) 0.8375(5) 0.0282(17) Uani 1 1 d . . . C8 C 0.5148(9) 0.7272(9) 0.8547(5) 0.0333(17) Uani 1 1 d . . . C9 C 0.3218(9) 0.6087(9) 0.8639(5) 0.0344(19) Uani 1 1 d . . . H9 H 0.2772 0.4829 0.8713 0.041 Uiso 1 1 calc R . . C10 C 0.2011(9) 0.6829(10) 0.8618(5) 0.0396(19) Uani 1 1 d . . . H10 H 0.0748 0.6088 0.8711 0.048 Uiso 1 1 calc R . . C11 C 0.2643(10) 0.8640(10) 0.8462(6) 0.0416(19) Uani 1 1 d . . . H11 H 0.1782 0.9094 0.8419 0.050 Uiso 1 1 calc R . . C12 C 0.4534(10) 0.9821(9) 0.8367(5) 0.0351(18) Uani 1 1 d . . . H12 H 0.4956 1.1077 0.8298 0.042 Uiso 1 1 calc R . . H1N H 0.889(9) 1.071(9) 0.876(6) 0.06(3) 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 0.0419(15) 0.0356(12) 0.0489(15) 0.0133(11) 0.0143(11) 0.0107(10) S2 0.0366(13) 0.0355(11) 0.0389(13) 0.0128(10) 0.0095(10) 0.0179(10) O1 0.022(3) 0.038(3) 0.069(4) 0.010(3) 0.011(2) 0.000(2) O2 0.059(3) 0.050(3) 0.046(3) 0.023(2) 0.009(3) 0.030(3) O3 0.037(3) 0.049(3) 0.045(3) 0.010(2) 0.005(2) 0.024(2) O4 0.049(3) 0.038(3) 0.053(3) 0.020(2) 0.022(2) 0.022(2) N1 0.021(4) 0.034(3) 0.054(5) 0.007(3) 0.012(3) 0.019(3) C1 0.026(4) 0.046(5) 0.023(4) 0.013(4) 0.004(3) 0.025(3) C2 0.019(4) 0.027(4) 0.027(4) 0.002(4) 0.001(3) 0.012(3) C3 0.025(4) 0.033(4) 0.052(6) 0.008(4) -0.005(4) 0.017(3) C4 0.036(5) 0.042(5) 0.036(5) -0.007(4) 0.008(4) 0.017(4) C5 0.041(5) 0.048(5) 0.045(5) 0.024(5) 0.015(4) 0.028(4) C6 0.036(5) 0.030(4) 0.059(6) 0.012(4) 0.019(4) 0.017(3) C7 0.045(5) 0.027(4) 0.018(4) 0.014(3) 0.016(3) 0.019(4) C8 0.039(5) 0.031(4) 0.022(4) 0.000(4) -0.002(3) 0.018(3) C9 0.021(4) 0.026(4) 0.039(5) -0.002(3) 0.007(3) 0.005(4) C10 0.033(5) 0.036(5) 0.044(5) 0.010(4) 0.016(4) 0.014(4) C11 0.038(5) 0.042(5) 0.050(5) 0.008(4) 0.011(4) 0.027(4) C12 0.046(5) 0.029(4) 0.039(5) 0.013(4) 0.019(4) 0.023(4) _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 O1 1.424(4) . ? S1 O2 1.446(5) . ? S1 N1 1.594(5) . ? S1 C1 1.773(6) . ? S2 O4 1.421(4) . ? S2 O3 1.445(4) . ? S2 C8 1.751(6) . ? S2 C2 1.781(6) . ? N1 C7 1.463(7) . ? C1 C6 1.376(8) . ? C1 C2 1.420(8) . ? C2 C3 1.378(7) . ? C3 C4 1.386(8) . ? C4 C5 1.343(8) . ? C5 C6 1.371(7) . ? C7 C12 1.346(8) . ? C7 C8 1.414(8) . ? C8 C9 1.407(7) . ? C9 C10 1.370(8) . ? C10 C11 1.362(8) . ? C11 C12 1.383(8) . ? 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 O1 S1 O2 119.5(3) . . ? O1 S1 N1 106.1(3) . . ? O2 S1 N1 107.6(3) . . ? O1 S1 C1 106.5(3) . . ? O2 S1 C1 106.6(3) . . ? N1 S1 C1 110.3(3) . . ? O4 S2 O3 117.8(3) . . ? O4 S2 C8 108.3(3) . . ? O3 S2 C8 109.2(3) . . ? O4 S2 C2 107.0(3) . . ? O3 S2 C2 107.8(3) . . ? C8 S2 C2 106.2(3) . . ? C7 N1 S1 118.4(4) . . ? C6 C1 C2 117.5(6) . . ? C6 C1 S1 114.3(6) . . ? C2 C1 S1 128.2(5) . . ? C3 C2 C1 118.3(6) . . ? C3 C2 S2 116.1(5) . . ? C1 C2 S2 125.6(5) . . ? C2 C3 C4 121.5(6) . . ? C5 C4 C3 120.4(6) . . ? C4 C5 C6 119.0(7) . . ? C5 C6 C1 123.2(7) . . ? C12 C7 C8 120.0(6) . . ? C12 C7 N1 120.9(6) . . ? C8 C7 N1 118.9(6) . . ? C9 C8 C7 119.7(6) . . ? C9 C8 S2 120.0(5) . . ? C7 C8 S2 120.3(5) . . ? C10 C9 C8 118.5(6) . . ? C11 C10 C9 120.6(6) . . ? C10 C11 C12 121.5(7) . . ? C7 C12 C11 119.6(7) . . ? _diffrn_measured_fraction_theta_max 0.727 _diffrn_reflns_theta_full 25.87 _diffrn_measured_fraction_theta_full 0.727 _refine_diff_density_max 0.342 _refine_diff_density_min -0.264 _refine_diff_density_rms 0.071 #===END data_5b*(Me2SO4) _database_code_depnum_ccdc_archive 'CCDC 745480' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C26 H22 Cl2 N2 O7 S3' _chemical_formula_weight 641.54 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 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' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 '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' Cl Cl 0.3639 0.7018 '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/a loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z' '-x, -y, -z' 'x-1/2, -y-1/2, z' _cell_length_a 8.4934(4) _cell_length_b 40.567(2) _cell_length_c 8.9646(7) _cell_angle_alpha 90.00 _cell_angle_beta 112.706(6) _cell_angle_gamma 90.00 _cell_volume 2849.4(3) _cell_formula_units_Z 4 _cell_measurement_temperature 298 _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.44 _exptl_crystal_size_min 0.36 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.495 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1320 _exptl_absorpt_coefficient_mu 4.523 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.114 _exptl_absorpt_correction_T_max 0.179 _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.29.2 (release 20-01-2006 CrysAlis171 .NET) (compiled Jan 20 2006,12:36:28) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 298 _diffrn_radiation_wavelength 1.54018 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'Enhance (Cu) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Xcalibur3 4 circles diffractometer' _diffrn_measurement_method 'intensity from \w scans' _diffrn_detector_area_resol_mean 16.4547 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11997 _diffrn_reflns_av_R_equivalents 0.0309 _diffrn_reflns_av_sigmaI/netI 0.0421 _diffrn_reflns_limit_h_min -4 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 45 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 5.34 _diffrn_reflns_theta_max 62.27 _reflns_number_total 4254 _reflns_number_gt 2912 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlis CCD, Oxford Diffraction Ltd., Version 1.171.29.2 (release 20-01-2006 CrysAlis171 .NET) (compiled Jan 20 2006,12:36:28) ; _computing_cell_refinement ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.29.2 (release 20-01-2006 CrysAlis171 .NET) (compiled Jan 20 2006,12:36:28) ; _computing_data_reduction ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.29.2 (release 20-01-2006 CrysAlis171 .NET) (compiled Jan 20 2006,12:36:28) ; _computing_structure_solution 'SIR97 (Altomare, 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-3 (Farruggia, 1997)' _computing_publication_material 'PARST97 (Nardelli, 1995)' _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^)+(0.0737P)^2^+3.4353P] 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 SHELXL _refine_ls_extinction_coef 0.00077(15) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 4254 _refine_ls_number_parameters 371 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0820 _refine_ls_R_factor_gt 0.0598 _refine_ls_wR_factor_ref 0.1715 _refine_ls_wR_factor_gt 0.1633 _refine_ls_goodness_of_fit_ref 1.104 _refine_ls_restrained_S_all 1.104 _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 S1A S 0.85567(16) 0.82148(3) 0.27696(17) 0.0562(4) Uani 1 1 d . . . Cl1A Cl 1.2993(3) 0.75091(4) 0.8454(3) 0.1175(8) Uani 1 1 d . . . O1A O 0.8477(5) 0.84154(9) 0.1443(4) 0.0703(11) Uani 1 1 d . . . O2A O 0.9117(5) 0.78819(8) 0.2862(5) 0.0695(11) Uani 1 1 d . . . O3A O 0.8945(4) 0.87284(7) 0.6669(4) 0.0560(9) Uani 1 1 d . . . N1A N 0.9852(5) 0.84065(10) 0.4365(5) 0.0497(11) Uani 1 1 d . . . C1A C 0.6565(6) 0.82069(11) 0.2935(6) 0.0490(12) Uani 1 1 d . . . C2A C 0.5696(6) 0.84971(11) 0.2950(6) 0.0475(12) Uani 1 1 d . . . C3A C 0.4163(6) 0.84884(12) 0.3141(6) 0.0521(13) Uani 1 1 d . . . H3A H 0.3572 0.8682 0.3131 0.062 Uiso 1 1 calc R . . C4A C 0.3527(7) 0.81907(14) 0.3347(7) 0.0662(15) Uani 1 1 d . . . H4A H 0.2486 0.8184 0.3464 0.079 Uiso 1 1 calc R . . C5A C 0.4366(7) 0.79019(14) 0.3386(8) 0.0741(17) Uani 1 1 d . . . H5A H 0.3919 0.7703 0.3559 0.089 Uiso 1 1 calc R . . C6A C 0.5884(7) 0.79091(12) 0.3165(7) 0.0674(16) Uani 1 1 d . . . H6A H 0.6456 0.7713 0.3170 0.081 Uiso 1 1 calc R . . C7A C 1.0322(6) 0.82758(11) 0.5947(6) 0.0493(12) Uani 1 1 d . . . C8A C 0.9931(6) 0.84407(12) 0.7118(7) 0.0535(13) Uani 1 1 d . . . C9A C 1.0542(7) 0.83302(13) 0.8713(7) 0.0686(16) Uani 1 1 d . . . H9A H 1.0329 0.8449 0.9503 0.082 Uiso 1 1 calc R . . C10A C 1.1472(8) 0.80404(15) 0.9094(8) 0.0765(18) Uani 1 1 d . . . H10A H 1.1874 0.7961 1.0149 0.092 Uiso 1 1 calc R . . C11A C 1.1802(7) 0.78710(14) 0.7934(8) 0.0720(17) Uani 1 1 d . . . C12A C 1.1280(6) 0.79852(12) 0.6379(7) 0.0584(14) Uani 1 1 d . . . H12A H 1.1560 0.7871 0.5617 0.070 Uiso 1 1 calc R . . S1B S 0.73636(17) 0.94045(3) 0.62494(16) 0.0558(4) Uani 1 1 d . . . Cl1B Cl 0.2610(2) 0.99801(4) 0.0081(2) 0.0895(6) Uani 1 1 d . . . O1B O 0.9074(4) 0.94430(8) 0.7409(4) 0.0702(11) Uani 1 1 d . . . O2B O 0.6119(5) 0.96521(8) 0.6090(5) 0.0726(11) Uani 1 1 d . . . O3B O 0.6507(4) 0.87863(7) 0.2859(4) 0.0544(9) Uani 1 1 d . . . N1B N 0.7505(5) 0.93729(10) 0.4512(5) 0.0486(11) Uani 1 1 d . . . C1B C 0.6539(6) 0.90296(12) 0.6645(6) 0.0488(12) Uani 1 1 d . . . C2B C 0.7390(6) 0.87297(12) 0.6852(6) 0.0499(12) Uani 1 1 d . . . C3B C 0.6674(7) 0.84471(13) 0.7184(6) 0.0625(15) Uani 1 1 d . . . H3B H 0.7241 0.8246 0.7315 0.075 Uiso 1 1 calc R . . C4B C 0.5095(8) 0.84653(17) 0.7320(7) 0.0721(17) Uani 1 1 d . . . H4B H 0.4625 0.8277 0.7573 0.087 Uiso 1 1 calc R . . C5B C 0.4231(8) 0.87572(18) 0.7087(7) 0.0742(17) Uani 1 1 d . . . H5B H 0.3163 0.8765 0.7148 0.089 Uiso 1 1 calc R . . C6B C 0.4945(7) 0.90410(15) 0.6759(6) 0.0641(15) Uani 1 1 d . . . H6B H 0.4361 0.9240 0.6615 0.077 Uiso 1 1 calc R . . C7B C 0.6016(6) 0.93552(11) 0.3033(6) 0.0454(11) Uani 1 1 d . . . C8B C 0.5509(6) 0.90631(11) 0.2199(6) 0.0477(12) Uani 1 1 d . . . C9B C 0.4153(7) 0.90483(13) 0.0719(7) 0.0604(14) Uani 1 1 d . . . H9B H 0.3849 0.8849 0.0167 0.072 Uiso 1 1 calc R . . C10B C 0.3258(7) 0.93318(13) 0.0071(7) 0.0629(15) Uani 1 1 d . . . H10B H 0.2340 0.9326 -0.0923 0.075 Uiso 1 1 calc R . . C11B C 0.3732(7) 0.96244(12) 0.0904(7) 0.0567(14) Uani 1 1 d . . . C12B C 0.5104(6) 0.96409(12) 0.2367(6) 0.0545(13) Uani 1 1 d . . . H12B H 0.5419 0.9841 0.2904 0.065 Uiso 1 1 calc R . . S1S S 1.10933(18) 0.92457(3) 0.3122(2) 0.0673(5) Uani 1 1 d . . . O1S O 1.0416(4) 0.90867(8) 0.4268(4) 0.0593(9) Uani 1 1 d . . . C1S C 1.1199(9) 0.96726(15) 0.3552(10) 0.101(2) Uani 1 1 d . . . H1S1 H 1.2104 0.9714 0.4581 0.152 Uiso 1 1 calc R . . H1S2 H 1.0135 0.9744 0.3583 0.152 Uiso 1 1 calc R . . H1S3 H 1.1417 0.9792 0.2726 0.152 Uiso 1 1 calc R . . C2S C 0.9370(9) 0.92524(16) 0.1226(8) 0.089(2) Uani 1 1 d . . . H2S1 H 0.9134 0.9032 0.0807 0.134 Uiso 1 1 calc R . . H2S2 H 0.9660 0.9388 0.0490 0.134 Uiso 1 1 calc R . . H2S3 H 0.8379 0.9341 0.1349 0.134 Uiso 1 1 calc R . . H1NB H 0.828(6) 0.9260(12) 0.449(6) 0.051(16) Uiso 1 1 d . . . H1NA H 0.980(6) 0.8619(12) 0.425(6) 0.058(15) 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 S1A 0.0539(8) 0.0507(7) 0.0680(9) 0.0018(6) 0.0279(7) 0.0098(6) Cl1A 0.1204(16) 0.0811(12) 0.1279(17) 0.0317(11) 0.0225(13) 0.0487(11) O1A 0.079(3) 0.076(2) 0.064(2) 0.0150(19) 0.038(2) 0.013(2) O2A 0.068(2) 0.053(2) 0.092(3) -0.0065(19) 0.036(2) 0.0168(18) O3A 0.054(2) 0.0465(19) 0.075(2) 0.0075(16) 0.0338(19) 0.0048(16) N1A 0.048(3) 0.043(2) 0.064(3) 0.007(2) 0.028(2) 0.0016(19) C1A 0.040(3) 0.047(3) 0.055(3) -0.005(2) 0.012(3) 0.004(2) C2A 0.041(3) 0.041(3) 0.051(3) 0.000(2) 0.007(2) 0.003(2) C3A 0.035(3) 0.053(3) 0.063(3) -0.006(2) 0.013(3) 0.006(2) C4A 0.041(3) 0.072(4) 0.085(4) -0.001(3) 0.023(3) -0.008(3) C5A 0.062(4) 0.055(3) 0.101(5) 0.006(3) 0.027(4) -0.016(3) C6A 0.059(4) 0.042(3) 0.098(5) 0.002(3) 0.027(3) 0.003(2) C7A 0.037(3) 0.042(3) 0.065(3) 0.009(2) 0.015(3) -0.001(2) C8A 0.046(3) 0.045(3) 0.068(4) 0.002(2) 0.021(3) 0.000(2) C9A 0.081(4) 0.062(3) 0.061(4) 0.002(3) 0.025(3) 0.005(3) C10A 0.081(5) 0.071(4) 0.062(4) 0.014(3) 0.010(4) 0.003(3) C11A 0.058(4) 0.058(3) 0.089(5) 0.018(3) 0.016(4) 0.008(3) C12A 0.052(3) 0.050(3) 0.073(4) 0.010(3) 0.023(3) 0.007(2) S1B 0.0556(9) 0.0470(7) 0.0578(8) -0.0043(6) 0.0142(7) 0.0040(6) Cl1B 0.0934(12) 0.0688(10) 0.0902(12) 0.0260(8) 0.0177(10) 0.0327(8) O1B 0.054(2) 0.064(2) 0.069(3) -0.0053(19) -0.002(2) -0.0082(17) O2B 0.083(3) 0.058(2) 0.074(3) -0.0073(19) 0.027(2) 0.0220(19) O3B 0.0401(19) 0.0370(17) 0.077(2) 0.0018(16) 0.0122(18) 0.0048(14) N1B 0.038(3) 0.048(2) 0.057(3) 0.0046(19) 0.015(2) 0.004(2) C1B 0.044(3) 0.059(3) 0.040(3) -0.005(2) 0.013(2) 0.000(2) C2B 0.043(3) 0.056(3) 0.049(3) -0.002(2) 0.016(3) -0.004(2) C3B 0.061(4) 0.063(3) 0.060(4) 0.007(3) 0.020(3) -0.010(3) C4B 0.070(4) 0.095(5) 0.056(4) -0.002(3) 0.030(3) -0.027(4) C5B 0.054(4) 0.111(5) 0.064(4) -0.011(4) 0.029(3) -0.016(4) C6B 0.052(3) 0.086(4) 0.051(3) -0.009(3) 0.015(3) 0.005(3) C7B 0.041(3) 0.044(3) 0.051(3) 0.005(2) 0.017(3) 0.002(2) C8B 0.043(3) 0.043(3) 0.057(3) 0.000(2) 0.019(3) 0.007(2) C9B 0.054(3) 0.059(3) 0.059(4) -0.007(3) 0.011(3) 0.007(3) C10B 0.061(4) 0.069(4) 0.053(3) 0.005(3) 0.016(3) 0.015(3) C11B 0.060(4) 0.050(3) 0.062(4) 0.019(3) 0.026(3) 0.015(2) C12B 0.055(3) 0.044(3) 0.062(4) 0.008(2) 0.020(3) 0.007(2) S1S 0.0600(9) 0.0598(8) 0.0922(11) 0.0225(7) 0.0407(9) 0.0120(7) O1S 0.055(2) 0.053(2) 0.073(2) 0.0181(17) 0.029(2) 0.0029(16) C1S 0.108(6) 0.062(4) 0.139(7) 0.018(4) 0.052(5) -0.008(4) C2S 0.097(5) 0.088(4) 0.087(5) 0.024(4) 0.041(4) 0.010(4) _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 S1A O1A 1.421(4) . ? S1A O2A 1.424(3) . ? S1A N1A 1.627(4) . ? S1A C1A 1.754(5) . ? Cl1A C11A 1.741(6) . ? O3A C2B 1.392(5) . ? O3A C8A 1.402(6) . ? N1A C7A 1.419(6) . ? C1A C6A 1.389(7) . ? C1A C2A 1.392(6) . ? C2A O3B 1.378(5) . ? C2A C3A 1.379(6) . ? C3A C4A 1.364(7) . ? C4A C5A 1.365(8) . ? C5A C6A 1.379(8) . ? C7A C8A 1.389(7) . ? C7A C12A 1.400(6) . ? C8A C9A 1.393(7) . ? C9A C10A 1.384(8) . ? C10A C11A 1.363(8) . ? C11A C12A 1.370(8) . ? S1B O2B 1.425(3) . ? S1B O1B 1.432(4) . ? S1B N1B 1.613(5) . ? S1B C1B 1.767(5) . ? Cl1B C11B 1.730(5) . ? O3B C8B 1.394(5) . ? N1B C7B 1.438(6) . ? C1B C2B 1.390(7) . ? C1B C6B 1.397(7) . ? C2B C3B 1.383(7) . ? C3B C4B 1.395(8) . ? C4B C5B 1.366(8) . ? C5B C6B 1.384(8) . ? C7B C8B 1.378(6) . ? C7B C12B 1.394(6) . ? C8B C9B 1.382(7) . ? C9B C10B 1.377(7) . ? C10B C11B 1.377(7) . ? C11B C12B 1.379(7) . ? S1S O1S 1.503(3) . ? S1S C2S 1.764(7) . ? S1S C1S 1.769(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 O1A S1A O2A 119.9(2) . . ? O1A S1A N1A 105.1(2) . . ? O2A S1A N1A 107.7(2) . . ? O1A S1A C1A 110.2(2) . . ? O2A S1A C1A 106.8(2) . . ? N1A S1A C1A 106.3(2) . . ? C2B O3A C8A 117.3(4) . . ? C7A N1A S1A 122.3(3) . . ? C6A C1A C2A 118.8(5) . . ? C6A C1A S1A 119.9(4) . . ? C2A C1A S1A 121.1(4) . . ? O3B C2A C3A 123.1(4) . . ? O3B C2A C1A 116.1(4) . . ? C3A C2A C1A 120.6(4) . . ? C4A C3A C2A 118.8(5) . . ? C3A C4A C5A 122.3(5) . . ? C4A C5A C6A 119.1(5) . . ? C5A C6A C1A 120.4(5) . . ? C8A C7A C12A 118.7(5) . . ? C8A C7A N1A 121.2(4) . . ? C12A C7A N1A 120.0(5) . . ? C7A C8A C9A 121.2(5) . . ? C7A C8A O3A 118.4(5) . . ? C9A C8A O3A 120.4(5) . . ? C10A C9A C8A 118.5(6) . . ? C11A C10A C9A 120.4(6) . . ? C10A C11A C12A 121.7(5) . . ? C10A C11A Cl1A 119.4(5) . . ? C12A C11A Cl1A 118.9(5) . . ? C11A C12A C7A 119.4(5) . . ? O2B S1B O1B 120.1(2) . . ? O2B S1B N1B 106.7(2) . . ? O1B S1B N1B 106.1(2) . . ? O2B S1B C1B 106.9(2) . . ? O1B S1B C1B 108.5(2) . . ? N1B S1B C1B 108.0(2) . . ? C2A O3B C8B 118.4(3) . . ? C7B N1B S1B 121.8(3) . . ? C2B C1B C6B 119.2(5) . . ? C2B C1B S1B 123.6(4) . . ? C6B C1B S1B 117.2(4) . . ? C3B C2B C1B 120.3(5) . . ? C3B C2B O3A 122.5(5) . . ? C1B C2B O3A 117.1(4) . . ? C2B C3B C4B 119.5(5) . . ? C5B C4B C3B 120.7(5) . . ? C4B C5B C6B 120.0(5) . . ? C5B C6B C1B 120.3(5) . . ? C8B C7B C12B 118.5(5) . . ? C8B C7B N1B 121.5(4) . . ? C12B C7B N1B 119.9(4) . . ? C7B C8B C9B 121.9(4) . . ? C7B C8B O3B 116.8(4) . . ? C9B C8B O3B 121.1(4) . . ? C10B C9B C8B 119.2(5) . . ? C9B C10B C11B 119.5(5) . . ? C10B C11B C12B 121.4(5) . . ? C10B C11B Cl1B 119.3(4) . . ? C12B C11B Cl1B 119.3(4) . . ? C11B C12B C7B 119.5(5) . . ? O1S S1S C2S 105.7(3) . . ? O1S S1S C1S 105.8(3) . . ? C2S S1S C1S 98.5(3) . . ? _diffrn_measured_fraction_theta_max 0.938 _diffrn_reflns_theta_full 62.27 _diffrn_measured_fraction_theta_full 0.938 _refine_diff_density_max 0.261 _refine_diff_density_min -0.347 _refine_diff_density_rms 0.061 #===END data_15a*(Me2SO4) _database_code_depnum_ccdc_archive 'CCDC 745481' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C26 H24 N2 O5 S5' _chemical_formula_weight 604.77 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 triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.261(2) _cell_length_b 10.064(4) _cell_length_c 15.947(5) _cell_angle_alpha 99.54(3) _cell_angle_beta 90.98(2) _cell_angle_gamma 112.46(3) _cell_volume 1349.3(7) _cell_formula_units_Z 2 _cell_measurement_temperature 150 _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.55 _exptl_crystal_size_min 0.38 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.489 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 628 _exptl_absorpt_coefficient_mu 0.471 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.764 _exptl_absorpt_correction_T_max 0.829 _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.29.2 (release 20-01-2006 CrysAlis171 .NET) (compiled Jan 20 2006,12:36:28) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 150 _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Xcalibur3 4 circles diffractometer' _diffrn_measurement_method 'intensity from \w scans' _diffrn_detector_area_resol_mean 16.4547 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8850 _diffrn_reflns_av_R_equivalents 0.0162 _diffrn_reflns_av_sigmaI/netI 0.0746 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 3.85 _diffrn_reflns_theta_max 25.89 _reflns_number_total 4149 _reflns_number_gt 3006 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlis CCD, Oxford Diffraction Ltd., Version 1.171.29.2 (release 20-01-2006 CrysAlis171 .NET) (compiled Jan 20 2006,12:36:28) ; _computing_cell_refinement ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.29.2 (release 20-01-2006 CrysAlis171 .NET) (compiled Jan 20 2006,12:36:28) ; _computing_data_reduction ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.29.2 (release 20-01-2006 CrysAlis171 .NET) (compiled Jan 20 2006,12:36:28) ; _computing_structure_solution 'SIR97 (Altomare, 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-3 (Farruggia, 1997)' _computing_publication_material 'PARST97 (Nardelli, 1995)' _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^)+(0.0943P)^2^+12.6924P] 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 refU _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4149 _refine_ls_number_parameters 343 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1040 _refine_ls_R_factor_gt 0.0883 _refine_ls_wR_factor_ref 0.2933 _refine_ls_wR_factor_gt 0.2886 _refine_ls_goodness_of_fit_ref 1.252 _refine_ls_restrained_S_all 1.252 _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 S1A S 0.2725(3) 0.8308(3) 0.87193(16) 0.0374(7) Uani 1 1 d . . . S2A S 0.5490(3) 0.5899(3) 0.75581(16) 0.0379(7) Uani 1 1 d . . . O1A O 0.1561(8) 0.7456(8) 0.9200(4) 0.0465(19) Uani 1 1 d . . . O2A O 0.3328(9) 0.9840(8) 0.8916(5) 0.052(2) Uani 1 1 d . . . N1A N 0.4152(9) 0.7730(9) 0.8776(5) 0.038(2) Uani 1 1 d . . . C1A C 0.1913(9) 0.7806(9) 0.7632(6) 0.0237(19) Uani 1 1 d . . . C2A C 0.0969(10) 0.6325(10) 0.7249(6) 0.028(2) Uani 1 1 d . . . C3A C 0.0456(10) 0.6097(10) 0.6413(5) 0.026(2) Uani 1 1 d . . . H3A H -0.0179 0.5151 0.6143 0.031 Uiso 1 1 calc R . . C4A C 0.0837(10) 0.7212(11) 0.5941(6) 0.033(2) Uani 1 1 d . . . H4A H 0.0449 0.6993 0.5371 0.040 Uiso 1 1 calc R . . C5A C 0.1757(12) 0.8601(11) 0.6295(6) 0.037(2) Uani 1 1 d . . . H5A H 0.2025 0.9329 0.5967 0.044 Uiso 1 1 calc R . . C6A C 0.2320(11) 0.8953(11) 0.7176(6) 0.035(2) Uani 1 1 d . . . H6A H 0.2935 0.9910 0.7437 0.042 Uiso 1 1 calc R . . C7A C 0.5705(11) 0.8512(11) 0.8536(6) 0.034(2) Uani 1 1 d . . . C8A C 0.6511(12) 0.7832(12) 0.7973(6) 0.037(2) Uani 1 1 d . . . C9A C 0.7930(15) 0.8516(12) 0.7825(7) 0.049(3) Uani 1 1 d . . . H9A H 0.8394 0.8020 0.7450 0.059 Uiso 1 1 calc R . . C10A C 0.8825(14) 0.9978(14) 0.8201(8) 0.053(3) Uani 1 1 d . . . H10A H 0.9870 1.0446 0.8103 0.064 Uiso 1 1 calc R . . C11A C 0.8077(12) 1.0663(12) 0.8713(7) 0.043(3) Uani 1 1 d . . . H11A H 0.8629 1.1645 0.8950 0.052 Uiso 1 1 calc R . . C12A C 0.6528(12) 1.0001(12) 0.8911(7) 0.044(3) Uani 1 1 d . . . H12A H 0.6063 1.0515 0.9272 0.053 Uiso 1 1 calc R . . S1B S 0.3136(3) 0.2873(3) 0.63677(17) 0.0343(7) Uani 1 1 d . . . S2B S 0.0449(3) 0.4969(3) 0.78945(15) 0.0291(6) Uani 1 1 d . . . O1B O 0.4432(8) 0.2874(8) 0.6852(5) 0.0442(18) Uani 1 1 d . . . O2B O 0.2415(7) 0.1774(7) 0.5650(5) 0.0398(17) Uani 1 1 d . . . N1B N 0.1832(8) 0.2781(8) 0.7063(5) 0.0290(18) Uani 1 1 d . . . C1B C 0.3666(10) 0.4588(10) 0.6027(6) 0.030(2) Uani 1 1 d . . . C2B C 0.4583(10) 0.5901(10) 0.6548(6) 0.026(2) Uani 1 1 d . . . C3B C 0.4876(11) 0.7190(10) 0.6241(6) 0.031(2) Uani 1 1 d . . . H3B H 0.5510 0.8086 0.6573 0.037 Uiso 1 1 calc R . . C4B C 0.4224(11) 0.7136(12) 0.5440(6) 0.038(2) Uani 1 1 d . . . H4B H 0.4389 0.8005 0.5251 0.045 Uiso 1 1 calc R . . C5B C 0.3347(9) 0.5837(9) 0.4926(6) 0.024(2) Uani 1 1 d . . . H5B H 0.2967 0.5811 0.4378 0.029 Uiso 1 1 calc R . . C6B C 0.3031(10) 0.4563(10) 0.5233(6) 0.028(2) Uani 1 1 d . . . H6B H 0.2382 0.3674 0.4900 0.034 Uiso 1 1 calc R . . C7B C 0.0218(10) 0.2458(10) 0.6785(6) 0.028(2) Uani 1 1 d . . . C8B C -0.0559(9) 0.3340(10) 0.7155(6) 0.025(2) Uani 1 1 d . . . C9B C -0.2166(10) 0.2901(10) 0.6959(6) 0.033(2) Uani 1 1 d . . . H9B H -0.2685 0.3474 0.7209 0.039 Uiso 1 1 calc R . . C11B C -0.2260(10) 0.0751(10) 0.6019(6) 0.029(2) Uani 1 1 d . . . H11B H -0.2818 -0.0082 0.5613 0.035 Uiso 1 1 calc R . . C10B C -0.2978(11) 0.1625(11) 0.6397(6) 0.035(2) Uani 1 1 d . . . H10B H -0.4049 0.1345 0.6270 0.041 Uiso 1 1 calc R . . C12B C -0.0671(10) 0.1133(10) 0.6252(6) 0.028(2) Uani 1 1 d . . . H12B H -0.0199 0.0491 0.6049 0.034 Uiso 1 1 calc R . . S1S S 0.2087(4) 0.4089(4) 0.9594(2) 0.0623(9) Uani 1 1 d . . . O1S O 0.3311(9) 0.4631(10) 0.8972(6) 0.067(2) Uani 1 1 d . . . C1S C 0.269(3) 0.542(2) 1.0516(12) 0.132(8) Uani 1 1 d . . . H1SA H 0.2630 0.6302 1.0402 0.198 Uiso 1 1 calc R . . H1SB H 0.3757 0.5607 1.0700 0.198 Uiso 1 1 calc R . . H1SC H 0.2028 0.5080 1.0956 0.198 Uiso 1 1 calc R . . C2S C 0.230(2) 0.258(2) 0.9953(11) 0.106(6) Uani 1 1 d . . . H2SA H 0.1987 0.1757 0.9491 0.159 Uiso 1 1 calc R . . H2SB H 0.1657 0.2329 1.0413 0.159 Uiso 1 1 calc R . . H2SC H 0.3380 0.2848 1.0148 0.159 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 S1A 0.0392(14) 0.0368(15) 0.0345(14) -0.0004(12) 0.0004(11) 0.0159(12) S2A 0.0418(15) 0.0367(15) 0.0358(14) 0.0087(11) 0.0013(11) 0.0153(12) O1A 0.048(4) 0.048(5) 0.040(4) 0.004(4) 0.009(3) 0.016(4) O2A 0.058(5) 0.039(4) 0.055(5) -0.002(4) 0.003(4) 0.019(4) N1A 0.036(5) 0.038(5) 0.035(5) -0.007(4) -0.002(4) 0.015(4) C1A 0.018(4) 0.023(5) 0.027(5) 0.001(4) 0.002(4) 0.006(4) C2A 0.026(5) 0.025(5) 0.034(5) -0.001(4) 0.003(4) 0.013(4) C3A 0.020(4) 0.033(5) 0.022(5) 0.006(4) 0.002(4) 0.008(4) C4A 0.025(5) 0.037(6) 0.035(6) -0.001(5) 0.003(4) 0.012(4) C5A 0.043(6) 0.032(6) 0.038(6) 0.012(5) 0.005(5) 0.015(5) C6A 0.035(5) 0.031(5) 0.047(6) 0.008(5) 0.004(5) 0.022(5) C7A 0.028(5) 0.032(5) 0.038(6) 0.004(5) -0.004(4) 0.009(4) C8A 0.044(6) 0.042(6) 0.028(5) 0.003(5) -0.001(5) 0.021(5) C9A 0.068(8) 0.046(7) 0.030(6) 0.011(5) 0.005(6) 0.016(6) C10A 0.051(7) 0.059(8) 0.053(7) 0.017(6) 0.012(6) 0.021(6) C11A 0.034(6) 0.045(7) 0.042(6) 0.010(5) -0.001(5) 0.007(5) C12A 0.046(6) 0.044(7) 0.039(6) 0.004(5) -0.004(5) 0.017(5) S1B 0.0311(13) 0.0278(13) 0.0468(16) 0.0095(12) 0.0104(11) 0.0133(11) S2B 0.0279(12) 0.0307(13) 0.0261(12) 0.0023(10) -0.0001(10) 0.0097(10) O1B 0.035(4) 0.044(4) 0.062(5) 0.021(4) 0.011(3) 0.019(3) O2B 0.034(4) 0.029(4) 0.052(4) 0.003(3) 0.009(3) 0.008(3) N1B 0.020(4) 0.031(4) 0.037(5) 0.009(4) 0.002(3) 0.009(3) C1B 0.028(5) 0.027(5) 0.036(6) 0.003(4) 0.005(4) 0.012(4) C2B 0.022(4) 0.027(5) 0.031(5) 0.008(4) 0.006(4) 0.012(4) C3B 0.033(5) 0.024(5) 0.037(6) 0.009(4) 0.004(4) 0.013(4) C4B 0.035(5) 0.049(7) 0.027(5) 0.011(5) 0.004(4) 0.013(5) C5B 0.020(4) 0.026(5) 0.025(5) 0.007(4) 0.002(4) 0.007(4) C6B 0.024(5) 0.031(5) 0.029(5) 0.003(4) 0.009(4) 0.011(4) C7B 0.028(5) 0.027(5) 0.029(5) 0.002(4) -0.001(4) 0.010(4) C8B 0.018(4) 0.026(5) 0.027(5) 0.007(4) 0.005(4) 0.002(4) C9B 0.028(5) 0.029(5) 0.044(6) 0.011(5) 0.005(4) 0.011(4) C11B 0.025(5) 0.023(5) 0.034(5) -0.001(4) 0.000(4) 0.007(4) C10B 0.027(5) 0.032(6) 0.044(6) 0.010(5) 0.004(4) 0.010(4) C12B 0.024(5) 0.024(5) 0.036(5) 0.006(4) 0.004(4) 0.010(4) S1S 0.063(2) 0.072(2) 0.061(2) 0.0259(18) 0.0096(17) 0.0306(18) O1S 0.052(5) 0.080(6) 0.076(6) 0.020(5) 0.015(5) 0.031(5) C1S 0.21(2) 0.146(19) 0.102(15) 0.055(14) 0.062(15) 0.122(19) C2S 0.128(15) 0.149(18) 0.089(12) 0.046(12) 0.034(11) 0.095(14) _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 S1A O2A 1.401(8) . ? S1A O1A 1.423(8) . ? S1A N1A 1.641(8) . ? S1A C1A 1.789(9) . ? S2A C2B 1.804(9) . ? S2A C8A 1.806(11) . ? N1A C7A 1.445(13) . ? C1A C6A 1.400(13) . ? C1A C2A 1.429(12) . ? C2A C3A 1.361(12) . ? C2A S2B 1.770(10) . ? C3A C4A 1.391(13) . ? C4A C5A 1.346(13) . ? C5A C6A 1.427(14) . ? C7A C12A 1.414(14) . ? C7A C8A 1.428(14) . ? C8A C9A 1.276(15) . ? C9A C10A 1.404(16) . ? C10A C11A 1.348(16) . ? C11A C12A 1.399(15) . ? S1B O2B 1.403(7) . ? S1B O1B 1.416(7) . ? S1B N1B 1.641(8) . ? S1B C1B 1.785(10) . ? S2B C8B 1.762(9) . ? N1B C7B 1.447(11) . ? C1B C6B 1.379(13) . ? C1B C2B 1.384(13) . ? C2B C3B 1.393(13) . ? C3B C4B 1.387(13) . ? C4B C5B 1.361(13) . ? C5B C6B 1.377(13) . ? C7B C12B 1.392(13) . ? C7B C8B 1.408(13) . ? C8B C9B 1.394(12) . ? C9B C10B 1.369(13) . ? C11B C10B 1.365(13) . ? C11B C12B 1.398(12) . ? S1S O1S 1.519(9) . ? S1S C1S 1.74(2) . ? S1S C2S 1.785(17) . ? 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 O2A S1A O1A 120.8(5) . . ? O2A S1A N1A 110.0(5) . . ? O1A S1A N1A 104.7(5) . . ? O2A S1A C1A 106.3(5) . . ? O1A S1A C1A 107.0(4) . . ? N1A S1A C1A 107.6(4) . . ? C2B S2A C8A 102.0(4) . . ? C7A N1A S1A 122.9(7) . . ? C6A C1A C2A 122.5(8) . . ? C6A C1A S1A 115.3(7) . . ? C2A C1A S1A 122.1(7) . . ? C3A C2A C1A 115.8(9) . . ? C3A C2A S2B 125.1(7) . . ? C1A C2A S2B 118.9(7) . . ? C2A C3A C4A 123.1(9) . . ? C5A C4A C3A 121.1(9) . . ? C4A C5A C6A 119.8(9) . . ? C1A C6A C5A 117.6(9) . . ? C12A C7A C8A 117.3(9) . . ? C12A C7A N1A 119.3(9) . . ? C8A C7A N1A 123.3(9) . . ? C9A C8A C7A 122.1(10) . . ? C9A C8A S2A 121.0(9) . . ? C7A C8A S2A 116.6(8) . . ? C8A C9A C10A 123.2(12) . . ? C11A C10A C9A 116.0(11) . . ? C10A C11A C12A 124.6(11) . . ? C11A C12A C7A 116.7(10) . . ? O2B S1B O1B 120.4(4) . . ? O2B S1B N1B 108.2(4) . . ? O1B S1B N1B 103.6(4) . . ? O2B S1B C1B 107.1(4) . . ? O1B S1B C1B 109.3(4) . . ? N1B S1B C1B 107.7(4) . . ? C8B S2B C2A 103.1(4) . . ? C7B N1B S1B 120.7(6) . . ? C6B C1B C2B 120.7(9) . . ? C6B C1B S1B 116.9(7) . . ? C2B C1B S1B 122.3(7) . . ? C1B C2B C3B 118.2(8) . . ? C1B C2B S2A 119.8(7) . . ? C3B C2B S2A 121.9(7) . . ? C4B C3B C2B 120.1(9) . . ? C5B C4B C3B 121.2(10) . . ? C4B C5B C6B 118.9(9) . . ? C5B C6B C1B 120.9(9) . . ? C12B C7B C8B 118.2(8) . . ? C12B C7B N1B 119.9(8) . . ? C8B C7B N1B 121.0(8) . . ? C9B C8B C7B 119.9(8) . . ? C9B C8B S2B 118.9(7) . . ? C7B C8B S2B 121.2(6) . . ? C10B C9B C8B 119.9(9) . . ? C10B C11B C12B 118.6(9) . . ? C11B C10B C9B 121.9(9) . . ? C7B C12B C11B 121.2(8) . . ? O1S S1S C1S 105.8(9) . . ? O1S S1S C2S 108.5(7) . . ? C1S S1S C2S 101.5(9) . . ? _diffrn_measured_fraction_theta_max 0.789 _diffrn_reflns_theta_full 25.89 _diffrn_measured_fraction_theta_full 0.789 _refine_diff_density_max 0.850 _refine_diff_density_min -0.473 _refine_diff_density_rms 0.138