# Supplementary Material (ESI) for Perkin Transactions # This journal is © The Royal Society of Chemistry 2001 data_global _journal_coden_Cambridge 207 loop_ _publ_author_name 'Guillard, Jerome' 'Lamazzi, Christelle' 'Meth-Cohn, O.' 'Rees, Charles' 'White, Andrew J. P.' 'Williams, David J.' _publ_contact_author ; Prof Charles Rees Chemistry Department Imperial College LONDON SW7 2AY U.K. ; data_cwr0005 _database_code_CSD 157789 _audit_creation_method SHELXL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C19 H26 Cl N O S Si' _chemical_formula_weight 380.01 _chemical_melting_point ? _chemical_compound_source ? 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' 'O' 'O' 0.0492 0.0322 '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' 'S' 'S' 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Si' 'Si' 0.2541 0.3302 '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' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pbca loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 7.4927(10) _cell_length_b 17.788(4) _cell_length_c 30.694(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 4090.8(10) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 34 _cell_measurement_theta_min 11.20 _cell_measurement_theta_max 27.91 _exptl_crystal_description blocks _exptl_crystal_colour Colourless _exptl_crystal_size_max .88 _exptl_crystal_size_mid .67 _exptl_crystal_size_min .40 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.234 _exptl_crystal_density_method ? _exptl_crystal_F_000 1616 _exptl_absorpt_coefficient_mu 3.204 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.1438 _exptl_absorpt_correction_T_max 0.2907 _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'Siemens P4' _diffrn_measurement_method '\w scans' _diffrn_standards_number 3 _diffrn_standards_interval_count 97 _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3392 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0200 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 0 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 35 _diffrn_reflns_theta_min 2.88 _diffrn_reflns_theta_max 63.97 _reflns_number_total 3392 _reflns_number_observed 2853 _reflns_observed_criterion >2sigma(I) _computing_data_collection 'Siemens XSCANS' _computing_cell_refinement 'Siemens XSCANS' _computing_data_reduction 'Siemens SHELXTL' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics 'Siemens SHELXTL' _computing_publication_material 'Siemens SHELXTL' _refine_special_details ; Refinement on F^2^ for ALL reflections except for 144 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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 w=1/[\s^2^(Fo^2^)+(0.0682P)^2^+2.2039P] 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 ? _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0029(2) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 3248 _refine_ls_number_parameters 206 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0596 _refine_ls_R_factor_obs 0.0466 _refine_ls_wR_factor_all 0.1364 _refine_ls_wR_factor_obs 0.1232 _refine_ls_goodness_of_fit_all 1.046 _refine_ls_goodness_of_fit_obs 1.083 _refine_ls_restrained_S_all 1.098 _refine_ls_restrained_S_obs 1.083 _refine_ls_shift/esd_max 0.001 _refine_ls_shift/esd_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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group S1 S 0.45031(12) 0.91683(5) 0.27674(2) 0.0669(3) Uani 1 d . . N2 N 0.4807(3) 0.99121(14) 0.30712(8) 0.0602(6) Uani 1 d . . C3 C 0.4184(3) 0.97693(14) 0.34570(9) 0.0479(6) Uani 1 d . . Cl Cl 0.43894(11) 1.04899(4) 0.38302(3) 0.0699(3) Uani 1 d . . C4 C 0.3389(3) 0.90548(13) 0.35500(8) 0.0409(5) Uani 1 d . . C5 C 0.3503(3) 0.86519(14) 0.31663(8) 0.0449(6) Uani 1 d . . C6 C 0.2799(3) 0.7887(2) 0.30451(8) 0.0487(6) Uani 1 d . . O6 O 0.1233(3) 0.78296(12) 0.29430(7) 0.0668(6) Uani 1 d . . C7 C 0.4037(2) 0.72462(8) 0.30434(6) 0.0464(6) Uani 1 d G . C8 C 0.5852(2) 0.73393(9) 0.31196(6) 0.0587(7) Uani 1 d G . H8A H 0.6310(3) 0.78160(10) 0.31742(9) 0.070 Uiso 1 calc R . C9 C 0.6983(2) 0.67198(12) 0.31141(7) 0.0735(9) Uani 1 d G . H9A H 0.8198(2) 0.6782(2) 0.31651(11) 0.088 Uiso 1 calc R . C10 C 0.6299(3) 0.60074(10) 0.30324(8) 0.0772(10) Uani 1 d G . H10A H 0.7055(3) 0.55929(12) 0.30287(11) 0.093 Uiso 1 calc R . C11 C 0.4483(3) 0.59143(8) 0.29562(7) 0.0736(9) Uani 1 d G . H11A H 0.4025(4) 0.54376(9) 0.29015(11) 0.088 Uiso 1 calc R . C12 C 0.3353(2) 0.65337(10) 0.29617(6) 0.0565(7) Uani 1 d G . H12A H 0.2138(2) 0.64714(14) 0.29107(9) 0.068 Uiso 1 calc R . Si Si 0.21981(9) 0.87494(4) 0.40714(2) 0.0430(2) Uani 1 d . . C13 C 0.2062(5) 0.7692(2) 0.40838(9) 0.0642(8) Uani 1 d . . H13A H 0.1776(5) 0.7535(2) 0.37857(9) 0.077 Uiso 1 calc R . C14 C 0.0525(6) 0.7398(2) 0.43718(13) 0.106(2) Uani 1 d . . H14A H -0.0563(6) 0.7649(2) 0.42937(13) 0.159 Uiso 1 calc R . H14B H 0.0793(6) 0.7496(2) 0.46724(13) 0.159 Uiso 1 calc R . H14C H 0.0389(6) 0.6867(2) 0.43286(13) 0.159 Uiso 1 calc R . C15 C 0.3819(6) 0.7304(2) 0.41991(13) 0.0926(12) Uani 1 d . . H15A H 0.4753(6) 0.7496(2) 0.40161(13) 0.139 Uiso 1 calc R . H15B H 0.3702(6) 0.6772(2) 0.41550(13) 0.139 Uiso 1 calc R . H15C H 0.4105(6) 0.7402(2) 0.44986(13) 0.139 Uiso 1 calc R . C16 C 0.3351(4) 0.9150(2) 0.45665(9) 0.0556(7) Uani 1 d . . H16A H 0.3181(4) 0.9696(2) 0.45505(9) 0.067 Uiso 1 calc R . C17 C 0.2447(5) 0.8898(2) 0.49929(10) 0.0841(11) Uani 1 d . . H17A H 0.1184(5) 0.8979(2) 0.49722(10) 0.126 Uiso 1 calc R . H17B H 0.2918(5) 0.9184(2) 0.52320(10) 0.126 Uiso 1 calc R . H17C H 0.2677(5) 0.8373(2) 0.50403(10) 0.126 Uiso 1 calc R . C18 C 0.5363(4) 0.9026(2) 0.45913(11) 0.0747(9) Uani 1 d . . H18A H 0.5906(4) 0.9186(2) 0.43236(11) 0.112 Uiso 1 calc R . H18B H 0.5604(4) 0.8502(2) 0.46372(11) 0.112 Uiso 1 calc R . H18C H 0.5846(4) 0.9313(2) 0.48288(11) 0.112 Uiso 1 calc R . C19 C -0.0125(4) 0.9151(2) 0.40388(10) 0.0594(7) Uani 1 d . . H19A H -0.0791(4) 0.8947(2) 0.42869(10) 0.071 Uiso 1 calc R . C20 C -0.0202(5) 1.0003(2) 0.40770(13) 0.0822(11) Uani 1 d . . H20A H 0.0417(5) 1.0159(2) 0.43356(13) 0.123 Uiso 1 calc R . H20B H -0.1425(5) 1.0162(2) 0.40931(13) 0.123 Uiso 1 calc R . H20C H 0.0353(5) 1.0226(2) 0.38265(13) 0.123 Uiso 1 calc R . C21 C -0.1107(4) 0.8901(3) 0.36283(12) 0.0883(12) Uani 1 d . . H21A H -0.1056(4) 0.8364(3) 0.36047(12) 0.132 Uiso 1 calc R . H21B H -0.0552(4) 0.9124(3) 0.33776(12) 0.132 Uiso 1 calc R . H21C H -0.2330(4) 0.9059(3) 0.36442(12) 0.132 Uiso 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 0.0720(5) 0.0773(5) 0.0514(4) 0.0032(3) 0.0171(4) -0.0112(4) N2 0.0545(14) 0.0606(14) 0.066(2) 0.0082(11) 0.0104(12) -0.0076(12) C3 0.0347(13) 0.0464(13) 0.063(2) -0.0006(12) -0.0007(11) 0.0011(11) Cl 0.0712(5) 0.0518(4) 0.0868(6) -0.0131(4) 0.0026(4) -0.0101(3) C4 0.0297(11) 0.0460(12) 0.0470(13) 0.0009(10) -0.0012(10) 0.0004(10) C5 0.0361(12) 0.0523(14) 0.0464(13) -0.0005(11) 0.0036(11) -0.0006(11) C6 0.0447(15) 0.063(2) 0.0380(12) -0.0066(11) -0.0006(11) -0.0011(12) O6 0.0436(11) 0.0746(13) 0.0821(14) -0.0193(11) -0.0114(10) 0.0000(10) C7 0.0435(14) 0.0563(15) 0.0395(12) -0.0039(11) 0.0012(10) 0.0021(12) C8 0.0451(15) 0.070(2) 0.061(2) -0.0021(14) -0.0004(13) -0.0002(14) C9 0.047(2) 0.094(2) 0.080(2) 0.007(2) 0.004(2) 0.014(2) C10 0.074(2) 0.075(2) 0.083(2) 0.006(2) 0.015(2) 0.026(2) C11 0.078(2) 0.060(2) 0.083(2) -0.004(2) 0.014(2) 0.004(2) C12 0.053(2) 0.059(2) 0.058(2) -0.0065(13) 0.0046(13) -0.0019(14) Si 0.0356(4) 0.0525(4) 0.0410(4) -0.0030(3) 0.0041(3) -0.0005(3) C13 0.086(2) 0.059(2) 0.0477(15) 0.0021(12) 0.0094(15) -0.010(2) C14 0.146(4) 0.079(2) 0.093(3) -0.002(2) 0.048(3) -0.040(3) C15 0.137(4) 0.064(2) 0.077(2) -0.002(2) -0.009(2) 0.027(2) C16 0.050(2) 0.068(2) 0.0485(14) -0.0092(13) 0.0005(12) 0.0022(14) C17 0.078(2) 0.128(3) 0.046(2) -0.010(2) 0.006(2) 0.006(2) C18 0.051(2) 0.103(3) 0.070(2) -0.008(2) -0.015(2) 0.002(2) C19 0.0374(14) 0.084(2) 0.057(2) -0.0062(14) 0.0069(12) 0.0023(14) C20 0.059(2) 0.091(2) 0.097(3) -0.009(2) 0.003(2) 0.029(2) C21 0.044(2) 0.133(3) 0.088(2) -0.024(2) -0.015(2) 0.012(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 N2 1.635(3) . ? S1 C5 1.704(3) . ? N2 C3 1.298(3) . ? C3 C4 1.432(3) . ? C3 Cl 1.726(3) . ? C4 C5 1.381(3) . ? C4 Si 1.911(2) . ? C5 C6 1.506(4) . ? C6 O6 1.219(3) . ? C6 C7 1.470(3) . ? C7 C8 1.39 . ? C7 C12 1.39 . ? C8 C9 1.39 . ? C9 C10 1.39 . ? C10 C11 1.39 . ? C11 C12 1.39 . ? Si C19 1.884(3) . ? Si C13 1.885(3) . ? Si C16 1.888(3) . ? C13 C15 1.527(5) . ? C13 C14 1.543(4) . ? C16 C18 1.526(4) . ? C16 C17 1.540(4) . ? C19 C20 1.522(5) . ? C19 C21 1.525(4) . ? 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 N2 S1 C5 95.04(12) . . ? C3 N2 S1 108.2(2) . . ? N2 C3 C4 120.3(2) . . ? N2 C3 Cl 115.3(2) . . ? C4 C3 Cl 124.3(2) . . ? C5 C4 C3 105.4(2) . . ? C5 C4 Si 126.5(2) . . ? C3 C4 Si 127.8(2) . . ? C4 C5 C6 131.1(2) . . ? C4 C5 S1 111.1(2) . . ? C6 C5 S1 117.6(2) . . ? O6 C6 C7 122.8(2) . . ? O6 C6 C5 118.5(2) . . ? C7 C6 C5 118.7(2) . . ? C8 C7 C12 120.0 . . ? C8 C7 C6 121.64(15) . . ? C12 C7 C6 118.36(15) . . ? C9 C8 C7 120.0 . . ? C10 C9 C8 120.0 . . ? C9 C10 C11 120.0 . . ? C10 C11 C12 120.0 . . ? C11 C12 C7 120.0 . . ? C19 Si C13 109.2(2) . . ? C19 Si C16 108.80(13) . . ? C13 Si C16 112.69(14) . . ? C19 Si C4 106.19(12) . . ? C13 Si C4 109.02(12) . . ? C16 Si C4 110.67(12) . . ? C15 C13 C14 111.0(3) . . ? C15 C13 Si 114.1(2) . . ? C14 C13 Si 113.0(2) . . ? C18 C16 C17 110.5(3) . . ? C18 C16 Si 116.0(2) . . ? C17 C16 Si 111.9(2) . . ? C20 C19 C21 109.6(3) . . ? C20 C19 Si 114.1(2) . . ? C21 C19 Si 112.3(2) . . ? _refine_diff_density_max 0.208 _refine_diff_density_min -0.222 _refine_diff_density_rms 0.046 data_cwr0006 _database_code_CSD 157790 _audit_creation_method SHELXL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C19 H27 N O S Si' _chemical_formula_weight 345.57 _chemical_melting_point ? _chemical_compound_source ? 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' 'Si' 'Si' 0.2541 0.3302 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'S' 'S' 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.0792(13) _cell_length_b 8.1905(8) _cell_length_c 15.983(2) _cell_angle_alpha 77.493(6) _cell_angle_beta 86.740(12) _cell_angle_gamma 71.463(12) _cell_volume 978.9(2) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 26 _cell_measurement_theta_min 11.09 _cell_measurement_theta_max 27.91 _exptl_crystal_description needles _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.80 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_min 0.17 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.172 _exptl_crystal_density_method ? _exptl_crystal_F_000 372 _exptl_absorpt_coefficient_mu 2.072 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.5495 _exptl_absorpt_correction_T_max 0.9924 _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'Siemens P4' _diffrn_measurement_method '\w scans' _diffrn_standards_number 3 _diffrn_standards_interval_count 97 _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3312 _diffrn_reflns_av_R_equivalents 0.0267 _diffrn_reflns_av_sigmaI/netI 0.0207 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 0 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.83 _diffrn_reflns_theta_max 61.99 _reflns_number_total 3064 _reflns_number_observed 2750 _reflns_observed_criterion >2sigma(I) _computing_data_collection 'Siemens XSCANS' _computing_cell_refinement 'Siemens XSCANS' _computing_data_reduction 'Siemens SHELXTL' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics 'Siemens SHELXTL' _computing_publication_material 'Siemens SHELXTL' _refine_special_details ; Refinement on F^2^ for ALL reflections except for 77 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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 w=1/[\s^2^(Fo^2^)+(0.0554P)^2^+0.2860P] 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 ? _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0185(14) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 2987 _refine_ls_number_parameters 209 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0453 _refine_ls_R_factor_obs 0.0373 _refine_ls_wR_factor_all 0.1107 _refine_ls_wR_factor_obs 0.1006 _refine_ls_goodness_of_fit_all 1.059 _refine_ls_goodness_of_fit_obs 1.080 _refine_ls_restrained_S_all 1.124 _refine_ls_restrained_S_obs 1.080 _refine_ls_shift/esd_max 0.001 _refine_ls_shift/esd_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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group S1 S -0.31690(8) -0.07487(8) -0.18330(3) 0.0566(2) Uani 1 d . . N2 N -0.3953(2) -0.1167(2) -0.26617(11) 0.0528(5) Uani 1 d . . C3 C -0.4632(2) -0.2480(3) -0.24110(12) 0.0423(4) Uani 1 d . . C4 C -0.4544(2) -0.3136(3) -0.15082(12) 0.0432(5) Uani 1 d . . H4A H -0.4978(2) -0.4035(3) -0.12343(12) 0.052 Uiso 1 calc R . C5 C -0.3750(2) -0.2294(3) -0.10905(12) 0.0437(5) Uani 1 d . . C6 C -0.3525(3) -0.2546(3) -0.01480(12) 0.0483(5) Uani 1 d . . O6 O -0.4626(2) -0.2937(3) 0.03313(10) 0.0818(6) Uani 1 d . . C7 C -0.1960(2) -0.2305(2) 0.01843(11) 0.0395(4) Uani 1 d . . C8 C -0.0379(2) -0.2752(3) -0.02221(13) 0.0470(5) Uani 1 d . . H8A H -0.0304(2) -0.3140(3) -0.07324(13) 0.056 Uiso 1 calc R . C9 C 0.1097(3) -0.2627(3) 0.01225(15) 0.0566(6) Uani 1 d . . H9A H 0.2162(3) -0.2950(3) -0.01517(15) 0.068 Uiso 1 calc R . C10 C 0.0996(3) -0.2035(3) 0.08595(15) 0.0596(6) Uani 1 d . . H10A H 0.1991(3) -0.1953(3) 0.10895(15) 0.071 Uiso 1 calc R . C11 C -0.0566(3) -0.1558(3) 0.12638(14) 0.0638(6) Uani 1 d . . H11A H -0.0631(3) -0.1126(3) 0.17612(14) 0.077 Uiso 1 calc R . C12 C -0.2056(3) -0.1710(3) 0.09409(13) 0.0535(5) Uani 1 d . . H12A H -0.3108(3) -0.1417(3) 0.12285(13) 0.064 Uiso 1 calc R . Si Si -0.54977(6) -0.32605(7) -0.32744(3) 0.0390(2) Uani 1 d . . C13 C -0.6817(3) -0.4702(3) -0.27307(14) 0.0533(5) Uani 1 d . . H13A H -0.6079(3) -0.5544(3) -0.22606(14) 0.064 Uiso 1 calc R . C14 C -0.7220(4) -0.5815(4) -0.3301(2) 0.0855(9) Uani 1 d . . H14A H -0.6163(4) -0.6415(4) -0.3559(2) 0.128 Uiso 1 calc R . H14B H -0.8042(4) -0.5063(4) -0.3742(2) 0.128 Uiso 1 calc R . H14C H -0.7707(4) -0.6664(4) -0.2960(2) 0.128 Uiso 1 calc R . C15 C -0.8478(4) -0.3741(4) -0.2316(2) 0.0774(8) Uani 1 d . . H15A H -0.8209(4) -0.3050(4) -0.1960(2) 0.116 Uiso 1 calc R . H15B H -0.8969(4) -0.4584(4) -0.1971(2) 0.116 Uiso 1 calc R . H15C H -0.9304(4) -0.2983(4) -0.2753(2) 0.116 Uiso 1 calc R . C16 C -0.3563(3) -0.4617(3) -0.37983(13) 0.0515(5) Uani 1 d . . H16A H -0.4021(3) -0.5066(3) -0.42246(13) 0.062 Uiso 1 calc R . C17 C -0.2429(3) -0.3551(4) -0.4278(2) 0.0774(8) Uani 1 d . . H17A H -0.3142(3) -0.2552(4) -0.4676(2) 0.116 Uiso 1 calc R . H17B H -0.1543(3) -0.4276(4) -0.4585(2) 0.116 Uiso 1 calc R . H17C H -0.1888(3) -0.3154(4) -0.3876(2) 0.116 Uiso 1 calc R . C18 C -0.2462(4) -0.6218(4) -0.3161(2) 0.0863(9) Uani 1 d . . H18A H -0.3196(4) -0.6871(4) -0.2866(2) 0.129 Uiso 1 calc R . H18B H -0.1922(4) -0.5833(4) -0.2754(2) 0.129 Uiso 1 calc R . H18C H -0.1576(4) -0.6955(4) -0.3463(2) 0.129 Uiso 1 calc R . C19 C -0.6701(3) -0.1224(3) -0.40746(13) 0.0492(5) Uani 1 d . . H19A H -0.5846(3) -0.0604(3) -0.42669(13) 0.059 Uiso 1 calc R . C20 C -0.7285(4) -0.1606(4) -0.4878(2) 0.0913(10) Uani 1 d . . H20A H -0.6324(4) -0.2427(4) -0.5100(2) 0.137 Uiso 1 calc R . H20B H -0.7680(4) -0.0531(4) -0.5301(2) 0.137 Uiso 1 calc R . H20C H -0.8222(4) -0.2099(4) -0.4741(2) 0.137 Uiso 1 calc R . C21 C -0.8200(3) 0.0079(3) -0.3706(2) 0.0738(7) Uani 1 d . . H21A H -0.7803(3) 0.0301(3) -0.3200(2) 0.111 Uiso 1 calc R . H21B H -0.9141(3) -0.0406(3) -0.3563(2) 0.111 Uiso 1 calc R . H21C H -0.8598(3) 0.1162(3) -0.4123(2) 0.111 Uiso 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 0.0720(4) 0.0679(4) 0.0445(3) -0.0092(2) -0.0098(2) -0.0422(3) N2 0.0652(11) 0.0626(11) 0.0400(9) -0.0089(8) -0.0095(8) -0.0324(9) C3 0.0395(10) 0.0494(11) 0.0399(10) -0.0108(8) -0.0041(8) -0.0147(8) C4 0.0414(10) 0.0542(11) 0.0395(10) -0.0091(8) -0.0026(8) -0.0223(9) C5 0.0367(10) 0.0597(12) 0.0383(10) -0.0120(9) -0.0045(8) -0.0182(9) C6 0.0388(10) 0.0710(14) 0.0403(10) -0.0134(9) -0.0008(8) -0.0231(10) O6 0.0583(10) 0.159(2) 0.0473(9) -0.0197(10) 0.0072(8) -0.0630(11) C7 0.0387(10) 0.0481(10) 0.0341(9) -0.0076(8) -0.0060(7) -0.0166(8) C8 0.0415(10) 0.0595(12) 0.0435(10) -0.0142(9) -0.0030(8) -0.0179(9) C9 0.0394(11) 0.0702(14) 0.0602(13) -0.0064(11) -0.0066(9) -0.0207(10) C10 0.0574(14) 0.0681(14) 0.0597(14) -0.0039(11) -0.0212(11) -0.0314(11) C11 0.082(2) 0.072(2) 0.0468(12) -0.0187(11) -0.0179(12) -0.0301(13) C12 0.0542(12) 0.0688(14) 0.0402(11) -0.0183(10) -0.0022(9) -0.0182(11) Si 0.0377(3) 0.0452(3) 0.0362(3) -0.0131(2) -0.0047(2) -0.0120(2) C13 0.0580(13) 0.0621(13) 0.0513(12) -0.0198(10) 0.0003(10) -0.0292(11) C14 0.104(2) 0.101(2) 0.088(2) -0.046(2) 0.014(2) -0.068(2) C15 0.074(2) 0.092(2) 0.083(2) -0.033(2) 0.0300(14) -0.045(2) C16 0.0475(11) 0.0556(12) 0.0476(11) -0.0173(9) -0.0027(9) -0.0062(9) C17 0.0590(15) 0.095(2) 0.074(2) -0.0229(15) 0.0191(13) -0.0183(14) C18 0.070(2) 0.075(2) 0.083(2) -0.0088(15) -0.0067(14) 0.0153(14) C19 0.0478(11) 0.0515(11) 0.0475(11) -0.0157(9) -0.0114(9) -0.0089(9) C20 0.120(2) 0.072(2) 0.070(2) -0.0201(14) -0.054(2) -0.001(2) C21 0.066(2) 0.0601(14) 0.080(2) -0.0175(13) -0.0037(13) 0.0044(12) _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 N2 1.644(2) . ? S1 C5 1.701(2) . ? N2 C3 1.335(3) . ? C3 C4 1.424(3) . ? C3 Si 1.891(2) . ? C4 C5 1.364(3) . ? C5 C6 1.489(3) . ? C6 O6 1.215(2) . ? C6 C7 1.484(3) . ? C7 C8 1.378(3) . ? C7 C12 1.388(3) . ? C8 C9 1.383(3) . ? C9 C10 1.357(3) . ? C10 C11 1.366(3) . ? C11 C12 1.388(3) . ? Si C16 1.879(2) . ? Si C13 1.881(2) . ? Si C19 1.884(2) . ? C13 C15 1.521(3) . ? C13 C14 1.533(3) . ? C16 C17 1.526(3) . ? C16 C18 1.527(3) . ? C19 C20 1.519(3) . ? C19 C21 1.524(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N2 S1 C5 95.48(9) . . ? C3 N2 S1 110.47(14) . . ? N2 C3 C4 113.6(2) . . ? N2 C3 Si 117.39(14) . . ? C4 C3 Si 129.02(15) . . ? C5 C4 C3 112.3(2) . . ? C4 C5 C6 127.4(2) . . ? C4 C5 S1 108.15(14) . . ? C6 C5 S1 124.30(15) . . ? O6 C6 C7 121.5(2) . . ? O6 C6 C5 119.5(2) . . ? C7 C6 C5 119.0(2) . . ? C8 C7 C12 119.1(2) . . ? C8 C7 C6 121.0(2) . . ? C12 C7 C6 119.8(2) . . ? C7 C8 C9 120.6(2) . . ? C10 C9 C8 120.2(2) . . ? C9 C10 C11 120.1(2) . . ? C10 C11 C12 120.8(2) . . ? C7 C12 C11 119.3(2) . . ? C16 Si C13 109.15(10) . . ? C16 Si C19 109.67(9) . . ? C13 Si C19 116.39(10) . . ? C16 Si C3 107.36(9) . . ? C13 Si C3 107.37(9) . . ? C19 Si C3 106.49(9) . . ? C15 C13 C14 110.3(2) . . ? C15 C13 Si 114.5(2) . . ? C14 C13 Si 113.8(2) . . ? C17 C16 C18 110.7(2) . . ? C17 C16 Si 113.2(2) . . ? C18 C16 Si 111.9(2) . . ? C20 C19 C21 110.8(2) . . ? C20 C19 Si 113.8(2) . . ? C21 C19 Si 114.8(2) . . ? _refine_diff_density_max 0.303 _refine_diff_density_min -0.204 _refine_diff_density_rms 0.036 data_CWR9910 _database_code_CSD 157791 _audit_creation_method SHELXL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C16 H11 N O3 S2' _chemical_formula_weight 329.38 _chemical_melting_point ? _chemical_compound_source ? 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 Monoclinic _symmetry_space_group_name_H-M C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 21.714(3) _cell_length_b 9.2748(8) _cell_length_c 15.3842(12) _cell_angle_alpha 90.00 _cell_angle_beta 101.432(9) _cell_angle_gamma 90.00 _cell_volume 3036.8(5) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 28 _cell_measurement_theta_min 4.86 _cell_measurement_theta_max 12.45 _exptl_crystal_description blocks _exptl_crystal_colour Clear _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.50 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.441 _exptl_crystal_density_method ? _exptl_crystal_F_000 1360 _exptl_absorpt_coefficient_mu 0.361 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _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 'Siemens P4' _diffrn_measurement_method '\w scans' _diffrn_standards_number 3 _diffrn_standards_interval_count 97 _diffrn_standards_interval_time ? _diffrn_standards_decay_% 4.40 _diffrn_reflns_number 2735 _diffrn_reflns_av_R_equivalents 0.0250 _diffrn_reflns_av_sigmaI/netI 0.0413 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 25 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.91 _diffrn_reflns_theta_max 24.99 _reflns_number_total 2660 _reflns_number_observed 2195 _reflns_observed_criterion >2sigma(I) _computing_data_collection 'Siemens XSCANS' _computing_cell_refinement 'Siemens XSCANS' _computing_data_reduction 'Siemens SHELXTL' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics 'Siemens SHELXTL' _computing_publication_material 'Siemens SHELXTL' _refine_special_details ; Refinement on F^2^ for ALL reflections except for 120 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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 w=1/[\s^2^(Fo^2^)+(0.0599P)^2^+0.5934P] 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 ? _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0014(4) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 2540 _refine_ls_number_parameters 176 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0516 _refine_ls_R_factor_obs 0.0400 _refine_ls_wR_factor_all 0.1080 _refine_ls_wR_factor_obs 0.0990 _refine_ls_goodness_of_fit_all 1.036 _refine_ls_goodness_of_fit_obs 1.071 _refine_ls_restrained_S_all 1.054 _refine_ls_restrained_S_obs 1.071 _refine_ls_shift/esd_max 0.000 _refine_ls_shift/esd_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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group S1 S 0.40197(3) 0.48857(7) 1.05459(5) 0.0480(2) Uani 1 d . . N2 N 0.36874(10) 0.3536(2) 0.99369(15) 0.0445(5) Uani 1 d . . C3 C 0.41048(10) 0.2508(2) 0.99599(14) 0.0352(5) Uani 1 d . . C4 C 0.47099(10) 0.2731(3) 1.04768(14) 0.0367(5) Uani 1 d . . H4A H 0.50401(10) 0.2076(3) 1.05431(14) 0.044 Uiso 1 calc R . C5 C 0.47357(10) 0.4062(3) 1.08657(14) 0.0368(5) Uani 1 d . . S6 S 0.38687(2) 0.08954(6) 0.93506(4) 0.0368(2) Uani 1 d . . O7 O 0.33678(9) 0.1255(2) 0.86253(12) 0.0504(5) Uani 1 d . . O8 O 0.44319(8) 0.0235(2) 0.91819(12) 0.0463(4) Uani 1 d . . C9 C 0.29352(6) -0.0127(2) 1.01349(11) 0.0544(7) Uani 1 d G . H9A H 0.26607(6) 0.0409(2) 0.97165(11) 0.065 Uiso 1 calc R . C10 C 0.27076(6) -0.0907(2) 1.07757(13) 0.0647(8) Uani 1 d G . H10A H 0.22808(6) -0.0892(3) 1.0786(2) 0.078 Uiso 1 calc R . C11 C 0.31178(9) -0.1709(2) 1.14011(12) 0.0589(7) Uani 1 d G . H11A H 0.29655(12) -0.2230(3) 1.1830(2) 0.071 Uiso 1 calc R . C12 C 0.37556(8) -0.1731(2) 1.13857(11) 0.0550(7) Uani 1 d G . H12A H 0.40300(11) -0.2267(3) 1.18041(14) 0.066 Uiso 1 calc R . C13 C 0.39832(6) -0.0951(2) 1.07449(11) 0.0469(6) Uani 1 d G . H13A H 0.44100(6) -0.0966(3) 1.0735(2) 0.056 Uiso 1 calc R . C14 C 0.35730(7) -0.0149(2) 1.01195(10) 0.0398(5) Uani 1 d G . C15 C 0.52519(11) 0.4895(3) 1.14348(15) 0.0391(5) Uani 1 d . . O15 O 0.51896(10) 0.6201(2) 1.14790(14) 0.0556(5) Uani 1 d . . C16 C 0.63699(7) 0.49590(13) 1.21605(10) 0.0436(5) Uani 1 d G . H16A H 0.63739(7) 0.59194(13) 1.19879(10) 0.052 Uiso 1 calc R . C17 C 0.69103(6) 0.4334(2) 1.26513(11) 0.0500(6) Uani 1 d G . H17A H 0.72758(7) 0.4876(2) 1.2807(2) 0.060 Uiso 1 calc R . C18 C 0.69043(6) 0.2898(2) 1.29093(12) 0.0534(6) Uani 1 d G . H18A H 0.72658(8) 0.2480(2) 1.3238(2) 0.064 Uiso 1 calc R . C19 C 0.63579(8) 0.20882(13) 1.26764(12) 0.0539(6) Uani 1 d G . H19A H 0.63539(11) 0.11278(15) 1.2849(2) 0.065 Uiso 1 calc R . C20 C 0.58175(6) 0.2713(2) 1.21856(11) 0.0446(5) Uani 1 d G . H20A H 0.54519(8) 0.2171(2) 1.2030(2) 0.054 Uiso 1 calc R . C21 C 0.58235(6) 0.4149(2) 1.19276(10) 0.0382(5) Uani 1 d G . 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 0.0435(3) 0.0401(3) 0.0580(4) -0.0041(3) 0.0045(3) 0.0107(2) N2 0.0373(10) 0.0424(11) 0.0513(12) -0.0009(9) 0.0030(8) 0.0057(8) C3 0.0325(10) 0.0386(11) 0.0338(10) 0.0032(9) 0.0048(8) 0.0021(9) C4 0.0338(10) 0.0411(11) 0.0341(10) -0.0003(9) 0.0036(8) 0.0043(9) C5 0.0363(11) 0.0395(11) 0.0343(10) 0.0040(9) 0.0064(8) 0.0041(9) S6 0.0328(3) 0.0426(3) 0.0327(3) -0.0015(2) 0.0007(2) 0.0013(2) O7 0.0430(9) 0.0620(11) 0.0402(9) 0.0026(8) -0.0065(7) 0.0002(8) O8 0.0428(9) 0.0511(10) 0.0455(9) -0.0065(8) 0.0098(7) 0.0044(8) C9 0.0387(13) 0.067(2) 0.0549(15) 0.0070(13) 0.0031(11) -0.0012(12) C10 0.0473(15) 0.080(2) 0.068(2) 0.006(2) 0.0159(13) -0.0114(15) C11 0.073(2) 0.050(2) 0.059(2) 0.0028(13) 0.0250(14) -0.0050(14) C12 0.071(2) 0.0414(13) 0.0537(15) 0.0068(11) 0.0159(13) 0.0118(13) C13 0.0486(13) 0.0425(13) 0.0504(13) 0.0018(10) 0.0120(11) 0.0097(11) C14 0.0410(12) 0.0377(11) 0.0396(12) -0.0039(9) 0.0058(9) -0.0015(9) C15 0.0445(12) 0.0395(12) 0.0338(11) -0.0018(9) 0.0086(9) -0.0014(10) O15 0.0586(11) 0.0394(10) 0.0640(12) -0.0060(8) 0.0009(9) 0.0036(8) C16 0.0485(13) 0.0429(13) 0.0385(11) -0.0009(10) 0.0066(9) -0.0066(10) C17 0.0411(12) 0.058(2) 0.0473(13) -0.0013(11) 0.0004(10) -0.0072(11) C18 0.0463(13) 0.062(2) 0.0480(13) 0.0045(12) 0.0002(11) 0.0055(12) C19 0.058(2) 0.0440(13) 0.0547(15) 0.0088(11) -0.0004(12) 0.0010(12) C20 0.0462(12) 0.0450(13) 0.0401(12) 0.0033(10) 0.0022(9) -0.0071(10) C21 0.0424(12) 0.0424(12) 0.0291(10) -0.0022(9) 0.0055(8) -0.0020(10) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 N2 1.642(2) . ? S1 C5 1.714(2) . ? N2 C3 1.311(3) . ? C3 C4 1.410(3) . ? C3 S6 1.785(2) . ? C4 C5 1.368(3) . ? C5 C15 1.493(3) . ? S6 O7 1.435(2) . ? S6 O8 1.436(2) . ? S6 C14 1.7469(13) . ? C9 C10 1.39 . ? C9 C14 1.39 . ? C10 C11 1.39 . ? C11 C12 1.39 . ? C12 C13 1.39 . ? C13 C14 1.39 . ? C15 O15 1.222(3) . ? C15 C21 1.490(3) . ? C16 C17 1.39 . ? C16 C21 1.39 . ? C17 C18 1.39 . ? C18 C19 1.39 . ? C19 C20 1.39 . ? C20 C21 1.39 . ? 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 N2 S1 C5 95.46(11) . . ? C3 N2 S1 108.4(2) . . ? N2 C3 C4 118.0(2) . . ? N2 C3 S6 118.0(2) . . ? C4 C3 S6 123.9(2) . . ? C5 C4 C3 109.4(2) . . ? C4 C5 C15 133.1(2) . . ? C4 C5 S1 108.7(2) . . ? C15 C5 S1 118.1(2) . . ? O7 S6 O8 119.98(11) . . ? O7 S6 C14 109.38(10) . . ? O8 S6 C14 109.04(10) . . ? O7 S6 C3 107.96(11) . . ? O8 S6 C3 106.61(11) . . ? C14 S6 C3 102.41(9) . . ? C10 C9 C14 120.0 . . ? C11 C10 C9 120.0 . . ? C10 C11 C12 120.0 . . ? C11 C12 C13 120.0 . . ? C12 C13 C14 120.0 . . ? C13 C14 C9 120.0 . . ? C13 C14 S6 119.63(9) . . ? C9 C14 S6 120.30(9) . . ? O15 C15 C21 121.5(2) . . ? O15 C15 C5 117.8(2) . . ? C21 C15 C5 120.7(2) . . ? C17 C16 C21 120.0 . . ? C16 C17 C18 120.0 . . ? C17 C18 C19 120.0 . . ? C20 C19 C18 120.0 . . ? C21 C20 C19 120.0 . . ? C20 C21 C16 120.0 . . ? C20 C21 C15 122.41(13) . . ? C16 C21 C15 117.54(13) . . ? _refine_diff_density_max 0.528 _refine_diff_density_min -0.244 _refine_diff_density_rms 0.051 data_CWR9911 _database_code_CSD 157792 _audit_creation_method SHELXL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C16 H11 N O S2' _chemical_formula_weight 297.38 _chemical_melting_point ? _chemical_compound_source ? 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 8.8669(9) _cell_length_b 8.9717(10) _cell_length_c 10.3455(11) _cell_angle_alpha 88.032(7) _cell_angle_beta 68.422(7) _cell_angle_gamma 68.794(6) _cell_volume 708.86(13) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 27 _cell_measurement_theta_min 5.00 _cell_measurement_theta_max 12.49 _exptl_crystal_description prisms _exptl_crystal_colour 'Pale pink' _exptl_crystal_size_max 0.70 _exptl_crystal_size_mid 0.53 _exptl_crystal_size_min 0.47 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.393 _exptl_crystal_density_method ? _exptl_crystal_F_000 308 _exptl_absorpt_coefficient_mu 0.369 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _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 'Siemens P4' _diffrn_measurement_method '\w scans' _diffrn_standards_number 3 _diffrn_standards_interval_count 97 _diffrn_standards_interval_time ? _diffrn_standards_decay_% 3.02 _diffrn_reflns_number 2656 _diffrn_reflns_av_R_equivalents 0.0284 _diffrn_reflns_av_sigmaI/netI 0.0379 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.13 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2481 _reflns_number_observed 1974 _reflns_observed_criterion >2sigma(I) _computing_data_collection 'Siemens XSCANS' _computing_cell_refinement 'Siemens XSCANS' _computing_data_reduction 'Siemens SHELXTL' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics 'Siemens SHELXTL' _computing_publication_material 'Siemens SHELXTL' _refine_special_details ; Refinement on F^2^ for ALL reflections except for 130 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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 w=1/[\s^2^(Fo^2^)+(0.0627P)^2^+0.1008P] 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 ? _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0227(73) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 2351 _refine_ls_number_parameters 158 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0549 _refine_ls_R_factor_obs 0.0415 _refine_ls_wR_factor_all 0.1193 _refine_ls_wR_factor_obs 0.1077 _refine_ls_goodness_of_fit_all 1.045 _refine_ls_goodness_of_fit_obs 1.082 _refine_ls_restrained_S_all 1.061 _refine_ls_restrained_S_obs 1.082 _refine_ls_shift/esd_max 0.000 _refine_ls_shift/esd_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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group S1 S 0.32456(9) 0.35489(8) 0.07162(7) 0.0562(2) Uani 1 d . . N2 N 0.1285(3) 0.4931(3) 0.1491(2) 0.0534(5) Uani 1 d . . C3 C 0.0946(3) 0.6045(3) 0.0656(2) 0.0434(5) Uani 1 d . . C4 C 0.2314(3) 0.5784(3) -0.0682(2) 0.0470(5) Uani 1 d . . H4A H 0.2259(3) 0.6457(3) -0.1381(2) 0.056 Uiso 1 calc R . C5 C 0.3718(3) 0.4415(3) -0.0804(2) 0.0453(5) Uani 1 d . . C6 C -0.1996(2) 0.7536(2) 0.24946(15) 0.0594(7) Uani 1 d G . H6A H -0.1770(2) 0.6716(2) 0.30535(15) 0.071 Uiso 1 calc R . C7 C -0.3573(2) 0.8852(2) 0.29857(15) 0.0714(8) Uani 1 d G . H7A H -0.4403(3) 0.8913(3) 0.3873(2) 0.086 Uiso 1 calc R . C8 C -0.3911(2) 1.0078(2) 0.2150(2) 0.0706(8) Uani 1 d G . H8A H -0.4966(2) 1.0958(2) 0.2479(3) 0.085 Uiso 1 calc R . C9 C -0.2671(2) 0.9987(2) 0.0824(2) 0.0694(8) Uani 1 d G . H9A H -0.2897(3) 1.0807(2) 0.0265(3) 0.083 Uiso 1 calc R . C10 C -0.1093(2) 0.8671(2) 0.03325(14) 0.0584(7) Uani 1 d G . H10A H -0.0264(3) 0.8610(3) -0.0555(2) 0.070 Uiso 1 calc R . C11 C -0.0756(2) 0.7446(2) 0.1168(2) 0.0456(5) Uani 1 d G . C12 C 0.5427(3) 0.3629(3) -0.1964(2) 0.0480(5) Uani 1 d . . O12 O 0.6583(2) 0.2492(2) -0.1830(2) 0.0643(5) Uani 1 d . . S13 S 0.55863(9) 0.45100(9) -0.35466(7) 0.0632(3) Uani 1 d . . C14 C 0.9179(2) 0.3371(2) -0.4704(2) 0.0619(7) Uani 1 d G . H14A H 0.9088(2) 0.4164(2) -0.4093(2) 0.074 Uiso 1 calc R . C15 C 1.0815(2) 0.2356(2) -0.5628(2) 0.0704(8) Uani 1 d G . H15A H 1.1820(2) 0.2470(3) -0.5634(3) 0.084 Uiso 1 calc R . C16 C 1.0951(2) 0.1171(2) -0.6542(2) 0.0632(7) Uani 1 d G . H16A H 1.2046(2) 0.0491(3) -0.7160(2) 0.076 Uiso 1 calc R . C17 C 0.9450(2) 0.1000(2) -0.6532(2) 0.0667(8) Uani 1 d G . H17A H 0.9541(3) 0.0207(3) -0.7144(2) 0.080 Uiso 1 calc R . C18 C 0.7814(2) 0.2015(2) -0.5609(2) 0.0609(7) Uani 1 d G . H18A H 0.6809(2) 0.1901(3) -0.5602(3) 0.073 Uiso 1 calc R . C19 C 0.7678(2) 0.3200(2) -0.4695(2) 0.0512(6) Uani 1 d G . 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 0.0531(4) 0.0527(4) 0.0463(4) 0.0055(3) -0.0137(3) -0.0069(3) N2 0.0501(11) 0.0535(12) 0.0426(11) 0.0022(9) -0.0093(9) -0.0124(9) C3 0.0419(12) 0.0470(12) 0.0380(11) -0.0037(9) -0.0126(9) -0.0151(10) C4 0.0435(12) 0.0482(13) 0.0397(11) -0.0003(9) -0.0103(10) -0.0117(10) C5 0.0430(12) 0.0478(13) 0.0396(11) -0.0023(9) -0.0126(10) -0.0134(10) C6 0.0491(14) 0.063(2) 0.0509(14) -0.0008(12) -0.0059(11) -0.0172(12) C7 0.0460(15) 0.080(2) 0.061(2) -0.0120(15) 0.0036(12) -0.0161(14) C8 0.0435(14) 0.063(2) 0.082(2) -0.015(2) -0.0131(14) -0.0033(12) C9 0.055(2) 0.060(2) 0.075(2) 0.0044(14) -0.0201(14) -0.0050(13) C10 0.0479(13) 0.0569(15) 0.0514(14) 0.0010(11) -0.0102(11) -0.0072(11) C11 0.0390(11) 0.0493(12) 0.0412(11) -0.0047(9) -0.0097(9) -0.0133(10) C12 0.0433(12) 0.0465(13) 0.0448(12) -0.0037(10) -0.0134(10) -0.0094(10) O12 0.0553(11) 0.0575(11) 0.0524(10) 0.0024(8) -0.0139(8) 0.0027(9) S13 0.0493(4) 0.0665(5) 0.0434(4) 0.0038(3) -0.0078(3) 0.0020(3) C14 0.056(2) 0.063(2) 0.0521(15) -0.0114(12) -0.0098(12) -0.0158(13) C15 0.0488(15) 0.082(2) 0.060(2) -0.0109(15) -0.0059(13) -0.0158(14) C16 0.061(2) 0.056(2) 0.0454(14) -0.0038(11) -0.0041(12) -0.0075(13) C17 0.088(2) 0.054(2) 0.0429(13) -0.0036(11) -0.0097(13) -0.0239(15) C18 0.064(2) 0.070(2) 0.0442(13) 0.0020(12) -0.0144(12) -0.0259(14) C19 0.0492(13) 0.0501(13) 0.0359(11) 0.0012(10) -0.0069(10) -0.0075(10) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 N2 1.639(2) . ? S1 C5 1.708(2) . ? N2 C3 1.323(3) . ? C3 C4 1.422(3) . ? C3 C11 1.491(2) . ? C4 C5 1.365(3) . ? C5 C12 1.477(3) . ? C6 C7 1.39 . ? C6 C11 1.39 . ? C7 C8 1.39 . ? C8 C9 1.39 . ? C9 C10 1.39 . ? C10 C11 1.39 . ? C12 O12 1.204(3) . ? C12 S13 1.774(3) . ? S13 C19 1.7691(13) . ? C14 C15 1.39 . ? C14 C19 1.39 . ? C15 C16 1.39 . ? C16 C17 1.39 . ? C17 C18 1.39 . ? C18 C19 1.39 . ? 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 N2 S1 C5 94.97(11) . . ? C3 N2 S1 110.6(2) . . ? N2 C3 C4 114.7(2) . . ? N2 C3 C11 119.5(2) . . ? C4 C3 C11 125.7(2) . . ? C5 C4 C3 111.1(2) . . ? C4 C5 C12 131.9(2) . . ? C4 C5 S1 108.7(2) . . ? C12 C5 S1 119.4(2) . . ? C7 C6 C11 120.0 . . ? C8 C7 C6 120.0 . . ? C7 C8 C9 120.0 . . ? C10 C9 C8 120.0 . . ? C11 C10 C9 120.0 . . ? C10 C11 C6 120.0 . . ? C10 C11 C3 120.22(13) . . ? C6 C11 C3 119.77(13) . . ? O12 C12 C5 122.2(2) . . ? O12 C12 S13 124.1(2) . . ? C5 C12 S13 113.7(2) . . ? C19 S13 C12 101.09(10) . . ? C15 C14 C19 120.0 . . ? C14 C15 C16 120.0 . . ? C15 C16 C17 120.0 . . ? C18 C17 C16 120.0 . . ? C17 C18 C19 120.0 . . ? C18 C19 C14 120.0 . . ? C18 C19 S13 119.63(10) . . ? C14 C19 S13 120.36(10) . . ? _refine_diff_density_max 0.218 _refine_diff_density_min -0.204 _refine_diff_density_rms 0.043 data_#cwr9910 _database_code_CSD 157793 _audit_creation_method SHELXL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C11 H7 N O3 S' _chemical_formula_weight 233.24 _chemical_melting_point ? _chemical_compound_source ? 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 6.3133(3) _cell_length_b 10.9118(7) _cell_length_c 15.324(2) _cell_angle_alpha 90.00 _cell_angle_beta 96.850(6) _cell_angle_gamma 90.00 _cell_volume 1048.13(14) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 26 _cell_measurement_theta_min 10.98 _cell_measurement_theta_max 27.94 _exptl_crystal_description blocks _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.50 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.478 _exptl_crystal_density_method ? _exptl_crystal_F_000 480 _exptl_absorpt_coefficient_mu 2.690 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.2267 _exptl_absorpt_correction_T_max 0.3158 _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'Siemens P4' _diffrn_measurement_method '\w scans' _diffrn_standards_number 3 _diffrn_standards_interval_count 97 _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 1866 _diffrn_reflns_av_R_equivalents 0.0280 _diffrn_reflns_av_sigmaI/netI 0.0201 _diffrn_reflns_limit_h_min -3 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -3 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 4.99 _diffrn_reflns_theta_max 62.99 _reflns_number_total 1698 _reflns_number_observed 1548 _reflns_observed_criterion >2sigma(I) _computing_data_collection 'Siemens XSCANS' _computing_cell_refinement 'Siemens XSCANS' _computing_data_reduction 'Siemens SHELXTL' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics 'Siemens SHELXTL' _computing_publication_material 'Siemens SHELXTL' _refine_special_details ; Refinement on F^2^ for ALL reflections except for 32 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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 w=1/[\s^2^(Fo^2^)+(0.0480P)^2^+0.2228P] 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 ? _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0081(10) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 1666 _refine_ls_number_parameters 150 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0433 _refine_ls_R_factor_obs 0.0341 _refine_ls_wR_factor_all 0.1009 _refine_ls_wR_factor_obs 0.0905 _refine_ls_goodness_of_fit_all 1.106 _refine_ls_goodness_of_fit_obs 1.124 _refine_ls_restrained_S_all 1.193 _refine_ls_restrained_S_obs 1.124 _refine_ls_shift/esd_max 0.002 _refine_ls_shift/esd_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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group S1 S 0.32929(8) 0.51943(5) 0.08041(4) 0.0589(2) Uani 1 d . . N2 N 0.3101(3) 0.6568(2) 0.03770(12) 0.0567(4) Uani 1 d . . C3 C 0.1261(3) 0.7061(2) 0.05325(12) 0.0472(4) Uani 1 d . . C4 C -0.0047(3) 0.6336(2) 0.10045(12) 0.0467(4) Uani 1 d . . H4A H -0.1369(3) 0.6577(2) 0.11550(12) 0.056 Uiso 1 calc R . C5 C 0.0894(3) 0.5228(2) 0.12121(12) 0.0458(4) Uani 1 d . . C6 C 0.0101(3) 0.4123(2) 0.16359(12) 0.0471(4) Uani 1 d . . C7 C -0.1623(3) 0.4252(2) 0.22072(12) 0.0453(4) Uani 1 d . . C8 C -0.3036(3) 0.3274(2) 0.22385(14) 0.0553(5) Uani 1 d . . H8A H -0.2892(3) 0.2575(2) 0.19035(14) 0.066 Uiso 1 calc R . C9 C -0.4638(4) 0.3351(2) 0.2766(2) 0.0681(6) Uani 1 d . . H9A H -0.5594(4) 0.2706(2) 0.2782(2) 0.082 Uiso 1 calc R . C10 C -0.4844(4) 0.4375(3) 0.3273(2) 0.0738(7) Uani 1 d . . H10A H -0.5937(4) 0.4417(3) 0.3628(2) 0.089 Uiso 1 calc R . C11 C -0.3435(4) 0.5343(2) 0.32565(14) 0.0648(6) Uani 1 d . . H11A H -0.3567(4) 0.6029(2) 0.36059(14) 0.078 Uiso 1 calc R . C12 C -0.1833(3) 0.5286(2) 0.27194(13) 0.0515(5) Uani 1 d . . H12A H -0.0894(3) 0.5939(2) 0.26999(13) 0.062 Uiso 1 calc R . C13 C 0.0683(3) 0.8326(2) 0.02434(13) 0.0506(5) Uani 1 d . . O1 O 0.0869(2) 0.31311(13) 0.14891(11) 0.0656(4) Uani 1 d . . O2 O 0.1965(3) 0.88600(13) -0.02377(10) 0.0632(4) Uani 1 d D . H2A H 0.1593(51) 0.9644(10) -0.0355(23) 0.120(12) Uiso 1 d D . O3 O -0.0915(2) 0.88011(13) 0.04781(10) 0.0630(4) Uani 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 0.0554(3) 0.0527(3) 0.0717(4) 0.0066(2) 0.0204(2) 0.0107(2) N2 0.0585(10) 0.0513(10) 0.0634(10) 0.0040(8) 0.0208(8) 0.0019(8) C3 0.0563(11) 0.0408(9) 0.0463(10) 0.0008(8) 0.0131(8) 0.0001(8) C4 0.0505(10) 0.0413(9) 0.0500(10) 0.0029(8) 0.0135(8) 0.0034(8) C5 0.0493(10) 0.0414(10) 0.0477(10) 0.0004(7) 0.0092(8) 0.0017(7) C6 0.0506(10) 0.0369(10) 0.0527(10) 0.0013(8) 0.0014(8) 0.0032(7) C7 0.0497(10) 0.0368(9) 0.0485(10) 0.0073(7) 0.0020(8) -0.0001(7) C8 0.0592(11) 0.0420(10) 0.0633(12) 0.0068(8) 0.0010(9) -0.0048(8) C9 0.0618(13) 0.0642(14) 0.079(2) 0.0180(12) 0.0111(11) -0.0114(11) C10 0.0691(14) 0.084(2) 0.0723(14) 0.0174(13) 0.0267(11) 0.0033(12) C11 0.083(2) 0.0587(13) 0.0551(11) 0.0029(10) 0.0196(11) 0.0076(11) C12 0.0621(12) 0.0403(10) 0.0524(10) 0.0048(8) 0.0078(9) -0.0023(8) C13 0.0626(11) 0.0427(10) 0.0488(10) 0.0014(8) 0.0167(8) -0.0025(8) O1 0.0717(10) 0.0394(7) 0.0873(11) 0.0010(7) 0.0157(8) 0.0100(6) O2 0.0792(10) 0.0469(8) 0.0701(9) 0.0113(7) 0.0353(8) 0.0006(7) O3 0.0716(9) 0.0459(8) 0.0773(10) 0.0112(7) 0.0325(8) 0.0068(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 N2 1.635(2) . ? S1 C5 1.707(2) . ? N2 C3 1.327(2) . ? C3 C4 1.404(3) . ? C3 C13 1.483(3) . ? C4 C5 1.368(3) . ? C5 C6 1.484(3) . ? C6 O1 1.218(2) . ? C6 C7 1.483(3) . ? C7 C12 1.390(3) . ? C7 C8 1.395(3) . ? C8 C9 1.371(3) . ? C9 C10 1.375(4) . ? C10 C11 1.383(4) . ? C11 C12 1.379(3) . ? C13 O3 1.226(2) . ? C13 O2 1.296(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 N2 S1 C5 95.76(9) . . ? C3 N2 S1 108.91(13) . . ? N2 C3 C4 116.5(2) . . ? N2 C3 C13 120.8(2) . . ? C4 C3 C13 122.6(2) . . ? C5 C4 C3 110.6(2) . . ? C4 C5 C6 131.3(2) . . ? C4 C5 S1 108.25(14) . . ? C6 C5 S1 120.21(14) . . ? O1 C6 C7 122.0(2) . . ? O1 C6 C5 118.6(2) . . ? C7 C6 C5 119.4(2) . . ? C12 C7 C8 119.8(2) . . ? C12 C7 C6 122.5(2) . . ? C8 C7 C6 117.8(2) . . ? C9 C8 C7 119.6(2) . . ? C8 C9 C10 120.6(2) . . ? C9 C10 C11 120.4(2) . . ? C12 C11 C10 119.7(2) . . ? C11 C12 C7 120.0(2) . . ? O3 C13 O2 124.7(2) . . ? O3 C13 C3 119.2(2) . . ? O2 C13 C3 116.1(2) . . ? _refine_diff_density_max 0.175 _refine_diff_density_min -0.169 _refine_diff_density_rms 0.035