# Supplementary Material (ESI) for Perkin Transactions # This journal is © The Royal Society of Chemistry 2002 data_global _journal_coden_Cambridge 207 _journal_volume ? _journal_year ? _journal_page_first ? _publ_requested_journal 'Perkin Transactions 1' loop_ _publ_author_name 'Rees, Charles' 'Sivadasan, Sivaprasad' 'White, A J.P.' 'Williams, D.' _publ_contact_author_name 'Prof Charles Rees' _publ_contact_author_address ; Prof Charles Rees Department of Chemistry Imperial College South Kensington London SW7 2AY UNITED KINGDOM ; _publ_contact_author_email 'C.REES@IC.AC.UK' _publ_section_title ; Conversion of tetrazoles into hydrazonoyl chlorides. Novel donor-dithiazolium interactions ; data_1 _database_code_CSD 180848 _audit_creation_method SHELXL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C2 N S2 Cl3' _chemical_formula_weight 208.50 _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' 'N' 'N' 0.0311 0.0180 '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 Orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) 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' _cell_length_a 5.9474(3) _cell_length_b 10.2280(6) _cell_length_c 10.9852(7) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 668.23(7) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 20 _cell_measurement_theta_min 11.01 _cell_measurement_theta_max 32.03 _exptl_crystal_description prisms _exptl_crystal_colour 'Dark brown' _exptl_crystal_size_max 0.05 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.072 _exptl_crystal_density_method ? _exptl_crystal_F_000 408 _exptl_absorpt_coefficient_mu 17.367 _exptl_absorpt_correction_type Ellipsoidal _exptl_absorpt_correction_T_min 0.3123 _exptl_absorpt_correction_T_max 0.4069 _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 680 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0223 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 0 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 5.91 _diffrn_reflns_theta_max 64.81 _reflns_number_total 680 _reflns_number_observed 638 _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 15 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^)+(0.0516P)^2^+0.0537P] 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 0.0046(9) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.40(7) _refine_ls_number_reflns 665 _refine_ls_number_parameters 75 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0334 _refine_ls_R_factor_obs 0.0290 _refine_ls_wR_factor_all 0.0726 _refine_ls_wR_factor_obs 0.0683 _refine_ls_goodness_of_fit_all 1.082 _refine_ls_goodness_of_fit_obs 1.094 _refine_ls_restrained_S_all 1.127 _refine_ls_restrained_S_obs 1.094 _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 0.7764(2) 0.33710(10) 0.67253(10) 0.0219(3) Uani 1 d . . S2 S 1.0471(2) 0.37458(10) 0.56491(10) 0.0219(3) Uani 1 d . . N3 N 1.0134(8) 0.5308(3) 0.5527(3) 0.0228(8) Uani 1 d . . C4 C 0.8371(9) 0.5795(4) 0.6096(4) 0.0217(10) Uani 1 d . . Cl4 Cl 0.7852(2) 0.74363(11) 0.60055(12) 0.0348(3) Uani 1 d . . C5 C 0.6976(8) 0.4941(4) 0.6752(4) 0.0202(9) Uani 1 d . . Cl5 Cl 0.4630(2) 0.53822(11) 0.75032(10) 0.0275(3) Uani 1 d . . Cl Cl 1.0182(2) 0.58869(10) 0.90100(9) 0.0228(3) 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 0.0246(5) 0.0189(5) 0.0220(5) -0.0004(4) 0.0025(5) -0.0013(4) S2 0.0242(6) 0.0185(5) 0.0230(5) 0.0001(4) 0.0038(4) 0.0009(4) N3 0.030(2) 0.016(2) 0.022(2) 0.0010(13) 0.001(2) 0.001(2) C4 0.030(3) 0.020(2) 0.015(2) -0.001(2) -0.004(2) 0.001(2) Cl4 0.0459(7) 0.0194(5) 0.0391(7) 0.0023(4) 0.0015(6) 0.0065(5) C5 0.019(2) 0.025(2) 0.016(2) -0.006(2) -0.002(2) 0.000(2) Cl5 0.0246(7) 0.0299(6) 0.0281(5) -0.0077(4) 0.0037(5) 0.0039(5) Cl 0.0239(6) 0.0222(5) 0.0223(5) -0.0009(3) 0.0025(5) -0.0017(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 C5 1.673(4) . ? S1 S2 2.034(2) . ? S2 N3 1.615(4) . ? N3 C4 1.319(7) . ? C4 C5 1.405(7) . ? C4 Cl4 1.709(4) . ? C5 Cl5 1.683(5) . ? Cl S1 2.9324(15) 3_756 ? Cl S2 2.9735(15) 3_756 ? Cl Cl5 3.1627(15) 1_655 ? Cl S2 3.173(2) 2_765 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C5 S1 S2 92.9(2) . . ? N3 S2 S1 97.9(2) . . ? C4 N3 S2 115.7(3) . . ? N3 C4 C5 118.5(4) . . ? N3 C4 Cl4 119.2(4) . . ? C5 C4 Cl4 122.3(4) . . ? C4 C5 S1 115.0(3) . . ? C4 C5 Cl5 125.1(4) . . ? S1 C5 Cl5 119.9(3) . . ? S1 Cl S2 40.28(3) 3_756 3_756 ? S1 Cl Cl5 69.45(4) 3_756 1_655 ? S2 Cl Cl5 109.62(4) 3_756 1_655 ? S1 Cl S2 73.41(4) 3_756 2_765 ? S2 Cl S2 85.33(4) 3_756 2_765 ? Cl5 Cl S2 68.59(4) 1_655 2_765 ? _refine_diff_density_max 0.294 _refine_diff_density_min -0.486 _refine_diff_density_rms 0.087 data_19 _database_code_CSD 180849 _audit_creation_method SHELXL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C5 N5 S3 Cl' _chemical_formula_weight 261.73 _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' 'N' 'N' 0.0061 0.0033 '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' 'Cl' 'Cl' 0.1484 0.1585 '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 10.947(3) _cell_length_b 6.065(2) _cell_length_c 14.001(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.48(2) _cell_angle_gamma 90.00 _cell_volume 929.6(4) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description plates _exptl_crystal_colour Yellow _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.43 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.870 _exptl_crystal_density_method ? _exptl_crystal_F_000 520 _exptl_absorpt_coefficient_mu 1.045 _exptl_absorpt_correction_type 'Face-indexed numerical' _exptl_absorpt_correction_T_min 0.6670 _exptl_absorpt_correction_T_max 0.8433 _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 2 _diffrn_standards_interval_count 50 _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 2835 _diffrn_reflns_av_R_equivalents 0.0187 _diffrn_reflns_av_sigmaI/netI 0.0238 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.86 _diffrn_reflns_theta_max 30.00 _reflns_number_total 2716 _reflns_number_observed 2365 _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 111 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^)+(0.0380P)^2^+0.2571P] 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 0.0310(30) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 2605 _refine_ls_number_parameters 128 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0354 _refine_ls_R_factor_obs 0.0288 _refine_ls_wR_factor_all 0.0806 _refine_ls_wR_factor_obs 0.0755 _refine_ls_goodness_of_fit_all 1.059 _refine_ls_goodness_of_fit_obs 1.085 _refine_ls_restrained_S_all 1.082 _refine_ls_restrained_S_obs 1.085 _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 0.91304(3) 0.27019(7) 0.56308(3) 0.03868(11) Uani 1 d . . S2 S 0.95238(4) 0.01425(8) 0.65693(3) 0.05015(14) Uani 1 d . . N3 N 0.81681(13) -0.1006(2) 0.65821(10) 0.0416(3) Uani 1 d . . C4 C 0.73573(13) -0.0079(2) 0.60549(10) 0.0323(3) Uani 1 d . . Cl4 Cl 0.59072(4) -0.11146(7) 0.60144(3) 0.04403(12) Uani 1 d . . C5 C 0.76254(12) 0.1873(2) 0.54844(9) 0.0297(3) Uani 1 d . . N6 N 0.67812(11) 0.2766(2) 0.49451(8) 0.0328(2) Uani 1 d . . C7 C 0.70752(12) 0.4622(2) 0.44549(9) 0.0307(3) Uani 1 d . . S8 S 0.59952(3) 0.59576(6) 0.37549(3) 0.03720(11) Uani 1 d . . C9 C 0.71104(13) 0.7853(2) 0.35233(10) 0.0327(3) Uani 1 d . . N10 N 0.81672(12) 0.7475(2) 0.39335(10) 0.0407(3) Uani 1 d . . N11 N 0.81433(12) 0.5604(2) 0.44678(10) 0.0396(3) Uani 1 d . . C12 C 0.69296(15) 0.9749(3) 0.29326(11) 0.0381(3) Uani 1 d . . N12 N 0.6779(2) 1.1272(3) 0.24700(12) 0.0546(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 0.0309(2) 0.0425(2) 0.0426(2) 0.01135(15) -0.00173(14) -0.00475(14) S2 0.0396(2) 0.0555(3) 0.0552(3) 0.0218(2) -0.0079(2) -0.0014(2) N3 0.0440(7) 0.0412(7) 0.0397(6) 0.0117(5) 0.0002(5) -0.0026(5) C4 0.0360(6) 0.0316(6) 0.0293(6) 0.0007(5) 0.0024(5) -0.0045(5) Cl4 0.0422(2) 0.0395(2) 0.0504(2) 0.0065(2) -0.0009(2) -0.01341(15) C5 0.0319(6) 0.0297(6) 0.0276(6) 0.0004(5) 0.0021(5) -0.0032(5) N6 0.0334(6) 0.0326(6) 0.0322(5) 0.0036(4) -0.0022(4) -0.0052(5) C7 0.0317(6) 0.0317(6) 0.0288(6) 0.0019(5) -0.0016(5) -0.0001(5) S8 0.0331(2) 0.0366(2) 0.0417(2) 0.00709(14) -0.00705(14) -0.00273(13) C9 0.0366(6) 0.0313(6) 0.0301(6) 0.0018(5) 0.0005(5) -0.0006(5) N10 0.0371(6) 0.0406(7) 0.0443(7) 0.0134(5) -0.0036(5) -0.0062(5) N11 0.0335(6) 0.0402(6) 0.0449(7) 0.0137(6) -0.0048(5) -0.0045(5) C12 0.0444(8) 0.0353(7) 0.0344(7) 0.0014(6) 0.0011(6) 0.0003(6) N12 0.0753(11) 0.0420(7) 0.0465(8) 0.0104(6) 0.0024(7) 0.0045(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 C5 1.7331(14) . ? S1 S2 2.0767(7) . ? S1 N11 2.6246(14) . ? S2 N3 1.6397(15) . ? N3 C4 1.280(2) . ? C4 C5 1.459(2) . ? C4 Cl4 1.7078(15) . ? C5 N6 1.306(2) . ? N6 C7 1.359(2) . ? C7 N11 1.312(2) . ? C7 S8 1.7308(14) . ? S8 C9 1.7098(15) . ? C9 N10 1.308(2) . ? C9 C12 1.430(2) . ? N10 N11 1.359(2) . ? N10 S2 3.0006(15) 3_766 ? N10 S1 3.018(2) 3_766 ? C12 N12 1.139(2) . ? N12 C4 3.111(2) 4_575 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C5 S1 S2 92.86(5) . . ? C5 S1 N11 74.64(6) . . ? S2 S1 N11 167.44(3) . . ? N3 S2 S1 98.13(5) . . ? C4 N3 S2 115.51(11) . . ? N3 C4 C5 122.03(13) . . ? N3 C4 Cl4 119.84(11) . . ? C5 C4 Cl4 118.12(11) . . ? N6 C5 C4 120.55(12) . . ? N6 C5 S1 127.99(11) . . ? C4 C5 S1 111.46(10) . . ? C5 N6 C7 117.78(12) . . ? N11 C7 N6 125.74(13) . . ? N11 C7 S8 113.55(11) . . ? N6 C7 S8 120.69(10) . . ? C9 S8 C7 86.37(7) . . ? N10 C9 C12 120.86(13) . . ? N10 C9 S8 115.42(11) . . ? C12 C9 S8 123.72(12) . . ? C9 N10 N11 111.54(12) . . ? C9 N10 S2 123.81(10) . 3_766 ? N11 N10 S2 123.45(9) . 3_766 ? C9 N10 S1 163.21(10) . 3_766 ? N11 N10 S1 83.25(8) . 3_766 ? S2 N10 S1 40.37(2) 3_766 3_766 ? C7 N11 N10 113.12(12) . . ? C7 N11 S1 93.79(9) . . ? N10 N11 S1 153.06(10) . . ? N12 C12 C9 179.2(2) . . ? C12 N12 C4 159.1(2) . 4_575 ? _refine_diff_density_max 0.326 _refine_diff_density_min -0.291 _refine_diff_density_rms 0.050 data_6 _database_code_CSD 180850 _audit_creation_method SHELXL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C5.50 H N5 S4 Cl4' _chemical_formula_weight 407.15 _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' 'S' 'S' 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Cl' 'Cl' 0.1484 0.1585 '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/m loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z' '-x, -y, -z' 'x, -y, z' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z' _cell_length_a 21.140(5) _cell_length_b 6.7242(15) _cell_length_c 10.004(3) _cell_angle_alpha 90.00 _cell_angle_beta 103.22(2) _cell_angle_gamma 90.00 _cell_volume 1384.4(6) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description needles _exptl_crystal_colour Yellow _exptl_crystal_size_max 0.48 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.953 _exptl_crystal_density_method ? _exptl_crystal_F_000 804 _exptl_absorpt_coefficient_mu 1.445 _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 2 _diffrn_standards_interval_count 50 _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 2459 _diffrn_reflns_av_R_equivalents 0.0177 _diffrn_reflns_av_sigmaI/netI 0.0278 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 29 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.98 _diffrn_reflns_theta_max 32.49 _reflns_number_total 2410 _reflns_number_observed 1942 _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 145 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^)+(0.0735P)^2^+0.0663P] 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 none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2265 _refine_ls_number_parameters 130 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0594 _refine_ls_R_factor_obs 0.0417 _refine_ls_wR_factor_all 0.1202 _refine_ls_wR_factor_obs 0.1060 _refine_ls_goodness_of_fit_all 1.084 _refine_ls_goodness_of_fit_obs 1.128 _refine_ls_restrained_S_all 1.142 _refine_ls_restrained_S_obs 1.127 _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 0.26296(3) 0.0000 0.68505(7) 0.0390(2) Uani 1 d S . S2 S 0.30370(4) 0.0000 0.51390(7) 0.0462(2) Uani 1 d S . N3 N 0.38057(11) 0.0000 0.5959(2) 0.0387(5) Uani 1 d S . C4 C 0.39175(12) 0.0000 0.7267(3) 0.0326(5) Uani 1 d S . Cl4 Cl 0.47007(3) 0.0000 0.82130(8) 0.0523(2) Uani 1 d S . C5 C 0.33879(11) 0.0000 0.7989(2) 0.0281(4) Uani 1 d S . N6 N 0.34929(10) 0.0000 0.9317(2) 0.0302(4) Uani 1 d S . N7 N 0.29227(9) 0.0000 0.9761(2) 0.0283(4) Uani 1 d S . C8 C 0.29739(12) 0.0000 1.1073(2) 0.0290(4) Uani 1 d S . Cl8 Cl 0.37136(3) 0.0000 1.22567(6) 0.0405(2) Uani 1 d S . N9 N 0.24550(10) 0.0000 1.1655(2) 0.0301(4) Uani 1 d S . C10 C 0.18747(11) 0.0000 1.0857(2) 0.0270(4) Uani 1 d S . S11 S 0.16612(3) 0.0000 0.90780(6) 0.0314(2) Uani 1 d S . S12 S 0.06705(3) 0.0000 0.90204(8) 0.0451(2) Uani 1 d S . N13 N 0.07253(11) 0.0000 1.0675(3) 0.0396(5) Uani 1 d S . C14 C 0.13019(12) 0.0000 1.1428(3) 0.0313(5) Uani 1 d S . Cl14 Cl 0.14005(4) 0.0000 1.31816(7) 0.0437(2) Uani 1 d S . C20 C 0.0041(13) 0.1258(26) 0.5195(35) 0.093(7) Uani 0.25 d PD -1 H20A H 0.0239(13) 0.2178(26) 0.4666(35) 0.112 Uiso 0.25 calc PR -1 H20B H -0.0034(13) 0.1961(26) 0.5992(35) 0.112 Uiso 0.25 calc PR -1 Cl21 Cl 0.0564(6) -0.0736(31) 0.5729(8) 0.128(6) Uani 0.25 d PD -1 Cl22 Cl -0.0705(5) 0.0418(19) 0.4187(5) 0.072(3) Uani 0.25 d PD -1 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 0.0256(3) 0.0588(4) 0.0326(3) 0.000 0.0064(2) 0.000 S2 0.0418(4) 0.0682(5) 0.0284(3) 0.000 0.0075(3) 0.000 N3 0.0350(12) 0.0513(14) 0.0332(10) 0.000 0.0150(9) 0.000 C4 0.0257(10) 0.0402(13) 0.0346(11) 0.000 0.0127(9) 0.000 Cl4 0.0249(3) 0.0836(6) 0.0491(4) 0.000 0.0098(3) 0.000 C5 0.0239(10) 0.0323(11) 0.0299(10) 0.000 0.0097(8) 0.000 N6 0.0244(9) 0.0391(11) 0.0291(9) 0.000 0.0105(7) 0.000 N7 0.0213(9) 0.0354(10) 0.0291(9) 0.000 0.0076(7) 0.000 C8 0.0267(10) 0.0340(11) 0.0274(9) 0.000 0.0084(8) 0.000 Cl8 0.0265(3) 0.0619(4) 0.0313(3) 0.000 0.0027(2) 0.000 N9 0.0271(9) 0.0372(10) 0.0278(8) 0.000 0.0103(7) 0.000 C10 0.0261(10) 0.0280(10) 0.0301(10) 0.000 0.0129(8) 0.000 S11 0.0251(3) 0.0412(3) 0.0298(3) 0.000 0.0101(2) 0.000 S12 0.0239(3) 0.0711(5) 0.0411(4) 0.000 0.0090(2) 0.000 N13 0.0272(10) 0.0520(14) 0.0442(12) 0.000 0.0179(9) 0.000 C14 0.0299(11) 0.0335(11) 0.0353(11) 0.000 0.0171(9) 0.000 Cl14 0.0468(4) 0.0546(4) 0.0364(3) 0.000 0.0231(3) 0.000 C20 0.078(9) 0.117(10) 0.072(19) -0.003(10) -0.008(9) 0.034(13) Cl21 0.126(7) 0.183(16) 0.081(4) 0.030(5) 0.033(4) 0.067(9) Cl22 0.083(2) 0.108(9) 0.0304(12) 0.004(2) 0.0217(12) 0.008(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 C5 1.741(2) . ? S1 S2 2.0852(11) . ? S1 N7 2.835(2) . ? S1 S11 3.3531(12) . ? S2 N3 1.644(3) . ? S2 Cl8 3.4995(13) 1_554 ? S2 Cl14 3.5645(15) 1_554 ? N3 C4 1.276(3) . ? C4 C5 1.464(3) . ? C4 Cl4 1.709(3) . ? C5 N6 1.296(3) . ? N6 N7 1.377(3) . ? N7 C8 1.291(3) . ? N7 S11 2.597(2) . ? C8 N9 1.354(3) . ? C8 Cl8 1.732(3) . ? N9 C10 1.302(3) . ? C10 C14 1.452(3) . ? C10 S11 1.733(2) . ? S11 S12 2.0818(10) . ? S11 Cl22 3.437(7) 5_556 ? S12 N13 1.633(3) . ? S12 N13 3.035(2) 5_557 ? S12 Cl22 3.239(4) 5_556 ? S12 Cl21 3.286(8) . ? N13 C14 1.278(4) . ? C14 Cl14 1.718(3) . ? C20 Cl21 1.74(2) . ? C20 Cl22 1.76(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 C5 S1 S2 92.62(8) . . ? C5 S1 N7 51.39(9) . . ? S2 S1 N7 144.01(5) . . ? C5 S1 S11 100.14(8) . . ? S2 S1 S11 167.24(4) . . ? N7 S1 S11 48.75(5) . . ? N3 S2 S1 97.87(9) . . ? N3 S2 Cl8 82.40(8) . 1_554 ? S1 S2 Cl8 179.74(4) . 1_554 ? N3 S2 Cl14 176.73(9) . 1_554 ? S1 S2 Cl14 85.40(4) . 1_554 ? Cl8 S2 Cl14 94.33(3) 1_554 1_554 ? C4 N3 S2 116.2(2) . . ? N3 C4 C5 121.5(2) . . ? N3 C4 Cl4 119.8(2) . . ? C5 C4 Cl4 118.7(2) . . ? N6 C5 C4 122.3(2) . . ? N6 C5 S1 125.9(2) . . ? C4 C5 S1 111.8(2) . . ? C5 N6 N7 111.9(2) . . ? C8 N7 N6 116.8(2) . . ? C8 N7 S11 96.3(2) . . ? N6 N7 S11 146.8(2) . . ? C8 N7 S1 172.4(2) . . ? N6 N7 S1 70.75(12) . . ? S11 N7 S1 76.08(6) . . ? N7 C8 N9 123.3(2) . . ? N7 C8 Cl8 123.2(2) . . ? N9 C8 Cl8 113.5(2) . . ? C10 N9 C8 118.6(2) . . ? N9 C10 C14 120.8(2) . . ? N9 C10 S11 128.1(2) . . ? C14 C10 S11 111.1(2) . . ? C10 S11 S12 93.01(8) . . ? C10 S11 N7 73.68(9) . . ? S12 S11 N7 166.70(6) . . ? C10 S11 S1 128.85(8) . . ? S12 S11 S1 138.14(4) . . ? N7 S11 S1 55.16(5) . . ? C10 S11 Cl22 159.1(2) . 5_556 ? S12 S11 Cl22 66.71(14) . 5_556 ? N7 S11 Cl22 126.53(14) . 5_556 ? S1 S11 Cl22 71.58(14) . 5_556 ? N13 S12 S11 97.71(9) . . ? N13 S12 N13 75.13(11) . 5_557 ? S11 S12 N13 172.84(6) . 5_557 ? N13 S12 Cl22 172.8(2) . 5_556 ? S11 S12 Cl22 77.1(2) . 5_556 ? N13 S12 Cl22 110.0(2) 5_557 5_556 ? N13 S12 Cl21 171.3(4) . . ? S11 S12 Cl21 82.3(2) . . ? N13 S12 Cl21 104.8(2) 5_557 . ? Cl22 S12 Cl21 6.3(5) 5_556 . ? C14 N13 S12 115.8(2) . . ? N13 C14 C10 122.4(2) . . ? N13 C14 Cl14 118.6(2) . . ? C10 C14 Cl14 119.0(2) . . ? Cl21 C20 Cl22 110.6(14) . . ? C20 Cl21 S12 94.8(13) . . ? _refine_diff_density_max 0.842 _refine_diff_density_min -0.721 _refine_diff_density_rms 0.101 data_7 _database_code_CSD 180851 _audit_creation_method SHELXL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C8 H6 N3 O2 S4 Cl' _chemical_formula_weight 339.85 _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' 'Cl' 'Cl' 0.3639 0.7018 '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 8.314(2) _cell_length_b 9.068(3) _cell_length_c 9.915(3) _cell_angle_alpha 112.17(2) _cell_angle_beta 97.07(2) _cell_angle_gamma 100.08(2) _cell_volume 666.8(3) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description blocks _exptl_crystal_colour Red _exptl_crystal_size_max 0.33 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_min 0.23 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.693 _exptl_crystal_density_method ? _exptl_crystal_F_000 344 _exptl_absorpt_coefficient_mu 8.390 _exptl_absorpt_correction_type Ellipsoidal _exptl_absorpt_correction_T_min 0.1507 _exptl_absorpt_correction_T_max 0.3120 _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 P3' _diffrn_measurement_method '\w scans' _diffrn_standards_number 2 _diffrn_standards_interval_count 50 _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 1774 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0195 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 4.92 _diffrn_reflns_theta_max 56.70 _reflns_number_total 1774 _reflns_number_observed 1609 _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 54 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^)+(0.0628P)^2^+0.6804P] 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 0.0064(12) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 1720 _refine_ls_number_parameters 164 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0439 _refine_ls_R_factor_obs 0.0382 _refine_ls_wR_factor_all 0.1153 _refine_ls_wR_factor_obs 0.1017 _refine_ls_goodness_of_fit_all 1.039 _refine_ls_goodness_of_fit_obs 1.060 _refine_ls_restrained_S_all 1.149 _refine_ls_restrained_S_obs 1.060 _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 0.36592(10) 0.35351(10) 0.56174(9) 0.0371(3) Uani 1 d . . S2 S 0.37587(11) 0.11765(10) 0.43374(10) 0.0419(3) Uani 1 d . . N3 N 0.2710(4) 0.1026(3) 0.2784(3) 0.0425(7) Uani 1 d . . C4 C 0.2165(4) 0.2283(4) 0.2811(4) 0.0369(8) Uani 1 d . . Cl4 Cl 0.10838(15) 0.21499(12) 0.11750(10) 0.0657(4) Uani 1 d . . C5 C 0.2485(4) 0.3731(4) 0.4178(3) 0.0317(7) Uani 1 d . . C6 C 0.1985(4) 0.5187(4) 0.4427(3) 0.0323(7) Uani 1 d . . N7 N 0.1031(3) 0.5490(3) 0.3359(3) 0.0377(7) Uani 1 d . . C8 C 0.0817(4) 0.6955(4) 0.3933(4) 0.0387(8) Uani 1 d . . S9 S 0.16799(12) 0.81741(11) 0.57967(10) 0.0478(3) Uani 1 d . . C10 C 0.2496(4) 0.6510(4) 0.5874(4) 0.0378(8) Uani 1 d . . O10 O 0.3368(3) 0.6540(3) 0.6971(3) 0.0515(7) Uani 1 d . . C11 C -0.0102(5) 0.7604(5) 0.3058(4) 0.0473(9) Uani 1 d . . N11 N -0.0836(5) 0.8134(5) 0.2387(4) 0.0666(10) Uani 1 d . . S20 S 0.55507(14) 0.30713(13) 0.86775(10) 0.0561(4) Uani 1 d . . O20 O 0.5625(4) 0.2112(3) 0.7095(3) 0.0557(7) Uani 1 d . . C21 C 0.7618(6) 0.3655(7) 0.9705(5) 0.083(2) Uani 1 d . . H21A H 0.8275(6) 0.4477(7) 0.9474(5) 0.124 Uiso 1 calc R . H21B H 0.8088(6) 0.2715(7) 0.9448(5) 0.124 Uiso 1 calc R . H21C H 0.7616(6) 0.4092(7) 1.0750(5) 0.124 Uiso 1 calc R . C22 C 0.4742(6) 0.1611(7) 0.9353(5) 0.0801(15) Uani 1 d . . H22A H 0.3580(6) 0.1140(7) 0.8901(5) 0.120 Uiso 1 calc R . H22B H 0.4868(6) 0.2138(7) 1.0414(5) 0.120 Uiso 1 calc R . H22C H 0.5340(6) 0.0761(7) 0.9113(5) 0.120 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 0.0446(5) 0.0392(5) 0.0329(5) 0.0193(4) 0.0077(4) 0.0135(4) S2 0.0519(6) 0.0367(5) 0.0440(5) 0.0213(4) 0.0106(4) 0.0164(4) N3 0.052(2) 0.038(2) 0.038(2) 0.0159(13) 0.0066(13) 0.0146(14) C4 0.045(2) 0.036(2) 0.031(2) 0.0157(15) 0.0061(14) 0.010(2) Cl4 0.0958(8) 0.0566(6) 0.0355(5) 0.0089(4) -0.0085(5) 0.0334(6) C5 0.034(2) 0.036(2) 0.031(2) 0.0189(14) 0.0084(13) 0.0079(14) C6 0.038(2) 0.032(2) 0.033(2) 0.0186(14) 0.0103(14) 0.0094(14) N7 0.043(2) 0.039(2) 0.038(2) 0.0209(13) 0.0109(12) 0.0132(13) C8 0.040(2) 0.040(2) 0.043(2) 0.022(2) 0.015(2) 0.014(2) S9 0.0592(6) 0.0358(5) 0.0480(6) 0.0136(4) 0.0135(4) 0.0171(4) C10 0.044(2) 0.035(2) 0.037(2) 0.015(2) 0.013(2) 0.0095(15) O10 0.066(2) 0.050(2) 0.0349(14) 0.0149(11) 0.0036(12) 0.0162(13) C11 0.051(2) 0.046(2) 0.055(2) 0.026(2) 0.016(2) 0.019(2) N11 0.076(2) 0.068(2) 0.075(2) 0.043(2) 0.012(2) 0.034(2) S20 0.0760(7) 0.0588(6) 0.0366(5) 0.0159(4) 0.0092(5) 0.0339(5) O20 0.081(2) 0.059(2) 0.0313(13) 0.0190(12) 0.0077(12) 0.0292(14) C21 0.077(3) 0.104(4) 0.048(3) 0.028(3) 0.001(2) -0.008(3) C22 0.075(3) 0.111(4) 0.055(3) 0.042(3) 0.016(2) 0.005(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 C5 1.712(3) . ? S1 S2 2.0570(14) . ? S1 O10 2.614(3) . ? S1 O20 2.839(3) . ? S2 N3 1.619(3) . ? S2 O20 2.711(3) . ? S2 O20 2.948(3) 2_656 ? N3 C4 1.290(5) . ? C4 C5 1.442(5) . ? C4 Cl4 1.706(3) . ? C5 C6 1.395(5) . ? C6 N7 1.384(4) . ? C6 C10 1.432(5) . ? N7 C8 1.287(4) . ? C8 C11 1.436(5) . ? C8 S9 1.733(4) . ? S9 C10 1.782(3) . ? C10 O10 1.220(4) . ? C11 N11 1.136(5) . ? S20 O20 1.495(3) . ? S20 C21 1.765(5) . ? S20 C22 1.767(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 C5 S1 S2 93.61(12) . . ? C5 S1 O10 80.04(13) . . ? S2 S1 O10 173.62(7) . . ? C5 S1 O20 158.36(12) . . ? S2 S1 O20 64.97(6) . . ? O10 S1 O20 121.32(8) . . ? N3 S2 S1 97.27(11) . . ? N3 S2 O20 168.01(13) . . ? S1 S2 O20 71.59(7) . . ? N3 S2 O20 91.88(12) . 2_656 ? S1 S2 O20 170.35(7) . 2_656 ? O20 S2 O20 99.03(7) . 2_656 ? C4 N3 S2 116.8(2) . . ? N3 C4 C5 120.4(3) . . ? N3 C4 Cl4 117.2(3) . . ? C5 C4 Cl4 122.3(3) . . ? C6 C5 C4 128.6(3) . . ? C6 C5 S1 119.5(2) . . ? C4 C5 S1 111.8(2) . . ? N7 C6 C5 124.9(3) . . ? N7 C6 C10 115.5(3) . . ? C5 C6 C10 119.6(3) . . ? C8 N7 C6 109.7(3) . . ? N7 C8 C11 121.3(3) . . ? N7 C8 S9 119.1(3) . . ? C11 C8 S9 119.5(3) . . ? C8 S9 C10 87.7(2) . . ? O10 C10 C6 127.1(3) . . ? O10 C10 S9 124.9(3) . . ? C6 C10 S9 107.9(2) . . ? C10 O10 S1 93.7(2) . . ? N11 C11 C8 178.8(4) . . ? O20 S20 C21 105.9(2) . . ? O20 S20 C22 106.0(2) . . ? C21 S20 C22 97.3(2) . . ? S20 O20 S2 138.3(2) . . ? S20 O20 S1 100.75(13) . . ? S2 O20 S1 43.44(5) . . ? _refine_diff_density_max 0.298 _refine_diff_density_min -0.333 _refine_diff_density_rms 0.062