#---Crystal 1, \b-form of chlorpropamide before the cooling cycle--# data_betaCPA_295K_before _audit_creation_method SHELXL-97 _chemical_name_systematic ; 4-chloro-N-((propylaminocarbonyl)benzenesulfonamide ; _chemical_name_common 'chlorpropamide, \b-form' _chemical_melting_point 'phase transition' _chemical_formula_moiety 'C10 H13 Cl N2 O3 S' _chemical_formula_sum 'C10 H13 Cl N2 O3 S' _chemical_formula_weight 276.73 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' 'Cl' 'Cl' 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P b c n' _symmetry_space_group_name_Hall '-P 2n 2ab' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y+1/2, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y, -z+1/2' '-x, -y, -z' 'x-1/2, y-1/2, -z-1/2' '-x-1/2, y-1/2, z' 'x, -y, z-1/2' _cell_length_a 14.7530(5) _cell_length_b 9.3034(3) _cell_length_c 19.1979(6) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2634.97(15) _cell_formula_units_Z 8 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 4156 _cell_measurement_theta_min 2.7562 _cell_measurement_theta_max 29.2847 _exptl_crystal_description 'block' _exptl_crystal_colour 'colourless' _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.395 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1152 _exptl_absorpt_coefficient_mu 0.446 _exptl_absorpt_correction_type 'multi-scan' _exptl_absorpt_correction_T_min 0.8833 _exptl_absorpt_correction_T_max 0.9652 _exptl_absorpt_process_details ; CrysAlis RED (Oxford Diffraction, 2008) ; _diffrn_ambient_temperature 295(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 'Oxford Diffraction KM4 CCD' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 10.3457 _diffrn_reflns_number 20652 _diffrn_reflns_av_R_equivalents 0.0608 _diffrn_reflns_av_sigmaI/netI 0.0517 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 2.76 _diffrn_reflns_theta_max 25.68 _reflns_number_total 2498 _reflns_number_gt 1178 _reflns_threshold_expression >2\s(I) _computing_data_collection 'CrysAlis CCD (Oxford Diffraction,2008)' _computing_cell_refinement 'CrysAlis RED (Oxford Diffraction,2008)' _computing_data_reduction 'CrysAlis RED (Oxford Diffraction,2008)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0755P)^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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2498 _refine_ls_number_parameters 155 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1019 _refine_ls_R_factor_gt 0.0444 _refine_ls_wR_factor_ref 0.1233 _refine_ls_wR_factor_gt 0.1102 _refine_ls_goodness_of_fit_ref 0.815 _refine_ls_restrained_S_all 0.815 _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 0.39983(5) 0.18483(8) 0.38205(4) 0.0703(3) Uani 1 1 d . . . Cl1 Cl 0.31475(9) 0.01007(13) 0.07575(5) 0.1247(5) Uani 1 1 d . . . N1 N 0.30576(16) 0.2508(2) 0.41319(12) 0.0673(7) Uani 1 1 d . . . H1 H 0.3052 0.3392 0.4263 0.081 Uiso 1 1 calc R . . N2 N 0.15342(18) 0.2474(2) 0.43410(12) 0.0689(7) Uani 1 1 d . . . H2 H 0.1584 0.3392 0.4375 0.083 Uiso 1 1 calc R . . O1 O 0.45952(14) 0.3048(2) 0.38146(12) 0.0927(7) Uani 1 1 d . . . O2 O 0.42393(14) 0.0581(2) 0.41917(10) 0.0821(6) Uani 1 1 d . . . O3 O 0.22730(14) 0.0402(2) 0.41145(11) 0.0774(6) Uani 1 1 d . . . C1 C 0.3377(2) 0.0595(4) 0.16072(16) 0.0768(9) Uani 1 1 d . . . C2 C 0.3484(3) 0.2003(4) 0.1767(2) 0.0974(11) Uani 1 1 d . . . H2A H 0.3426 0.2701 0.1423 0.117 Uiso 1 1 calc R . . C3 C 0.3678(2) 0.2396(3) 0.2446(2) 0.0910(10) Uani 1 1 d . . . H3 H 0.3760 0.3360 0.2558 0.109 Uiso 1 1 calc R . . C4 C 0.37518(18) 0.1364(3) 0.29550(15) 0.0623(8) Uani 1 1 d . . . C5 C 0.3637(2) -0.0049(3) 0.27800(16) 0.0779(9) Uani 1 1 d . . . H5 H 0.3684 -0.0757 0.3120 0.093 Uiso 1 1 calc R . . C6 C 0.3450(3) -0.0425(4) 0.20972(17) 0.0890(10) Uani 1 1 d . . . H6 H 0.3375 -0.1387 0.1978 0.107 Uiso 1 1 calc R . . C7 C 0.2266(2) 0.1712(3) 0.41956(13) 0.0586(7) Uani 1 1 d . . . C8 C 0.0650(2) 0.1824(4) 0.44464(19) 0.0889(10) Uani 1 1 d . . . H8A H 0.0331 0.2349 0.4808 0.107 Uiso 1 1 calc R . . H8B H 0.0730 0.0843 0.4606 0.107 Uiso 1 1 calc R . . C9 C 0.0076(3) 0.1819(4) 0.3786(3) 0.1308(18) Uani 1 1 d . . . H9A H -0.0006 0.2800 0.3626 0.157 Uiso 1 1 calc R . . H9B H 0.0395 0.1295 0.3424 0.157 Uiso 1 1 calc R . . C10 C -0.0810(3) 0.1161(5) 0.3898(3) 0.173(2) Uani 1 1 d . . . H10A H -0.0731 0.0187 0.4053 0.259 Uiso 1 1 calc R . . H10B H -0.1146 0.1168 0.3470 0.259 Uiso 1 1 calc R . . H10C H -0.1135 0.1694 0.4246 0.259 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S1 0.0706(5) 0.0561(5) 0.0843(6) -0.0057(4) -0.0086(4) -0.0004(4) Cl1 0.1655(11) 0.1451(10) 0.0635(6) 0.0035(6) 0.0063(6) 0.0059(7) N1 0.0770(17) 0.0415(12) 0.0835(17) -0.0114(12) 0.0048(13) -0.0052(12) N2 0.0804(18) 0.0499(13) 0.0763(17) -0.0044(12) 0.0103(13) 0.0023(14) O1 0.0763(15) 0.0748(14) 0.1268(19) -0.0132(13) -0.0059(12) -0.0172(12) O2 0.0945(15) 0.0669(13) 0.0847(14) -0.0015(11) -0.0201(12) 0.0214(12) O3 0.0869(15) 0.0405(11) 0.1049(16) -0.0032(10) 0.0108(12) -0.0011(10) C1 0.084(2) 0.087(2) 0.059(2) 0.0055(18) 0.0107(16) 0.0040(19) C2 0.118(3) 0.089(3) 0.085(3) 0.032(2) -0.004(2) -0.012(2) C3 0.113(3) 0.058(2) 0.102(3) 0.010(2) -0.002(2) -0.0155(18) C4 0.0594(18) 0.0494(17) 0.078(2) 0.0088(15) 0.0059(15) 0.0011(13) C5 0.113(3) 0.0534(19) 0.067(2) 0.0058(15) 0.0085(18) 0.0161(17) C6 0.133(3) 0.066(2) 0.068(2) -0.0065(18) 0.011(2) 0.009(2) C7 0.081(2) 0.0450(17) 0.0500(16) -0.0012(13) 0.0003(14) 0.0028(16) C8 0.084(2) 0.079(2) 0.104(3) -0.002(2) 0.030(2) 0.004(2) C9 0.080(3) 0.088(3) 0.225(5) 0.063(3) -0.026(3) -0.023(2) C10 0.116(4) 0.108(4) 0.295(7) 0.046(4) -0.001(4) -0.002(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 O1 1.422(2) . ? S1 O2 1.423(2) . ? S1 N1 1.631(2) . ? S1 C4 1.759(3) . ? Cl1 C1 1.728(3) . ? N1 C7 1.388(3) . ? N1 H1 0.8600 . ? N2 C7 1.321(3) . ? N2 C8 1.451(4) . ? N2 H2 0.8600 . ? O3 C7 1.229(3) . ? C1 C6 1.340(4) . ? C1 C2 1.355(5) . ? C2 C3 1.383(5) . ? C2 H2A 0.9300 . ? C3 C4 1.374(4) . ? C3 H3 0.9300 . ? C4 C5 1.367(4) . ? C5 C6 1.384(4) . ? C5 H5 0.9300 . ? C6 H6 0.9300 . ? C8 C9 1.525(5) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 C10 1.460(6) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? 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 119.98(13) . . ? O1 S1 N1 103.57(13) . . ? O2 S1 N1 109.93(13) . . ? O1 S1 C4 108.75(13) . . ? O2 S1 C4 108.21(12) . . ? N1 S1 C4 105.46(13) . . ? C7 N1 S1 123.20(18) . . ? C7 N1 H1 118.4 . . ? S1 N1 H1 118.4 . . ? C7 N2 C8 122.7(2) . . ? C7 N2 H2 118.6 . . ? C8 N2 H2 118.6 . . ? C6 C1 C2 121.0(3) . . ? C6 C1 Cl1 119.3(3) . . ? C2 C1 Cl1 119.6(3) . . ? C1 C2 C3 119.6(3) . . ? C1 C2 H2A 120.2 . . ? C3 C2 H2A 120.2 . . ? C4 C3 C2 120.1(3) . . ? C4 C3 H3 119.9 . . ? C2 C3 H3 119.9 . . ? C5 C4 C3 119.1(3) . . ? C5 C4 S1 120.3(2) . . ? C3 C4 S1 120.6(2) . . ? C4 C5 C6 120.0(3) . . ? C4 C5 H5 120.0 . . ? C6 C5 H5 120.0 . . ? C1 C6 C5 120.1(3) . . ? C1 C6 H6 119.9 . . ? C5 C6 H6 119.9 . . ? O3 C7 N2 124.4(3) . . ? O3 C7 N1 120.7(3) . . ? N2 C7 N1 114.9(2) . . ? N2 C8 C9 112.6(3) . . ? N2 C8 H8A 109.1 . . ? C9 C8 H8A 109.1 . . ? N2 C8 H8B 109.1 . . ? C9 C8 H8B 109.1 . . ? H8A C8 H8B 107.8 . . ? C10 C9 C8 112.1(4) . . ? C10 C9 H9A 109.2 . . ? C8 C9 H9A 109.2 . . ? C10 C9 H9B 109.2 . . ? C8 C9 H9B 109.2 . . ? H9A C9 H9B 107.9 . . ? C9 C10 H10A 109.5 . . ? C9 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C9 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 S1 N1 C7 176.6(2) . . . . ? O2 S1 N1 C7 -54.0(3) . . . . ? C4 S1 N1 C7 62.4(2) . . . . ? C6 C1 C2 C3 0.5(6) . . . . ? Cl1 C1 C2 C3 -179.2(3) . . . . ? C1 C2 C3 C4 -0.8(6) . . . . ? C2 C3 C4 C5 0.5(5) . . . . ? C2 C3 C4 S1 -179.9(3) . . . . ? O1 S1 C4 C5 144.7(3) . . . . ? O2 S1 C4 C5 12.8(3) . . . . ? N1 S1 C4 C5 -104.8(3) . . . . ? O1 S1 C4 C3 -34.9(3) . . . . ? O2 S1 C4 C3 -166.7(2) . . . . ? N1 S1 C4 C3 75.7(3) . . . . ? C3 C4 C5 C6 0.1(5) . . . . ? S1 C4 C5 C6 -179.5(3) . . . . ? C2 C1 C6 C5 0.0(5) . . . . ? Cl1 C1 C6 C5 179.8(3) . . . . ? C4 C5 C6 C1 -0.3(5) . . . . ? C8 N2 C7 O3 2.3(4) . . . . ? C8 N2 C7 N1 -178.2(3) . . . . ? S1 N1 C7 O3 10.9(4) . . . . ? S1 N1 C7 N2 -168.68(19) . . . . ? C7 N2 C8 C9 -95.0(4) . . . . ? N2 C8 C9 C10 179.9(4) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1 O3 0.86 1.95 2.737(3) 151.2 7_665 N2 H2 O2 0.86 2.40 3.121(3) 142.2 7_665 N2 H2 O3 0.86 2.57 3.273(3) 139.9 7_665 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.68 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.342 _refine_diff_density_min -0.238 _refine_diff_density_rms 0.042 #--Crystal 1, \b-form of chlorpropamide after the cooling cycle---# data_betaCPA_295K_after _audit_creation_method SHELXL-97 _chemical_name_systematic ; 4-chloro-N-((propylaminocarbonyl)benzenesulfonamide ; _chemical_name_common 'chlorpropamide, \b-form' _chemical_melting_point 'phase transition' _chemical_formula_moiety 'C10 H13 Cl N2 O3 S' _chemical_formula_sum 'C10 H13 Cl N2 O3 S' _chemical_formula_weight 276.73 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' 'Cl' 'Cl' 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P b c n' _symmetry_space_group_name_Hall '-P 2n 2ab' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y+1/2, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y, -z+1/2' '-x, -y, -z' 'x-1/2, y-1/2, -z-1/2' '-x-1/2, y-1/2, z' 'x, -y, z-1/2' _cell_length_a 14.7535(5) _cell_length_b 9.3041(3) _cell_length_c 19.1919(6) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2634.43(15) _cell_formula_units_Z 8 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 3564 _cell_measurement_theta_min 2.7933 _cell_measurement_theta_max 29.2399 _exptl_crystal_description 'block' _exptl_crystal_colour 'colourless' _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.395 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1152 _exptl_absorpt_coefficient_mu 0.446 _exptl_absorpt_correction_type 'multi-scan' _exptl_absorpt_correction_T_min 0.9188 _exptl_absorpt_correction_T_max 0.9652 _exptl_absorpt_process_details ; CrysAlis RED (Oxford Diffraction, 2008) ; _diffrn_ambient_temperature 295(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 'Oxford Diffraction KM4 CCD' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 10.3457 _diffrn_reflns_number 17312 _diffrn_reflns_av_R_equivalents 0.0557 _diffrn_reflns_av_sigmaI/netI 0.0523 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 2.80 _diffrn_reflns_theta_max 25.68 _reflns_number_total 2497 _reflns_number_gt 1163 _reflns_threshold_expression >2\s(I) _computing_data_collection 'CrysAlis CCD (Oxford Diffraction,2008)' _computing_cell_refinement 'CrysAlis RED (Oxford Diffraction,2008)' _computing_data_reduction 'CrysAlis RED (Oxford Diffraction,2008)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0746P)^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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2497 _refine_ls_number_parameters 155 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1043 _refine_ls_R_factor_gt 0.0445 _refine_ls_wR_factor_ref 0.1231 _refine_ls_wR_factor_gt 0.1103 _refine_ls_goodness_of_fit_ref 0.819 _refine_ls_restrained_S_all 0.819 _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 0.39984(5) 0.18481(8) 0.38209(4) 0.0710(3) Uani 1 1 d . . . Cl1 Cl 0.31475(9) 0.01006(13) 0.07572(5) 0.1256(5) Uani 1 1 d . . . N1 N 0.30571(16) 0.2509(2) 0.41322(12) 0.0679(7) Uani 1 1 d . . . H1 H 0.3051 0.3394 0.4262 0.081 Uiso 1 1 calc R . . N2 N 0.15381(18) 0.2474(3) 0.43423(12) 0.0696(7) Uani 1 1 d . . . H2 H 0.1588 0.3392 0.4376 0.084 Uiso 1 1 calc R . . O1 O 0.45943(13) 0.3046(2) 0.38146(12) 0.0929(7) Uani 1 1 d . . . O2 O 0.42397(14) 0.0582(2) 0.41913(10) 0.0830(6) Uani 1 1 d . . . O3 O 0.22726(13) 0.0403(2) 0.41147(11) 0.0781(6) Uani 1 1 d . . . C1 C 0.3375(2) 0.0603(4) 0.16078(16) 0.0785(9) Uani 1 1 d . . . C2 C 0.3483(3) 0.2004(4) 0.1769(2) 0.0976(11) Uani 1 1 d . . . H2A H 0.3425 0.2704 0.1426 0.117 Uiso 1 1 calc R . . C3 C 0.3680(2) 0.2395(4) 0.2447(2) 0.0920(10) Uani 1 1 d . . . H3 H 0.3762 0.3358 0.2560 0.110 Uiso 1 1 calc R . . C4 C 0.37538(18) 0.1364(3) 0.29552(15) 0.0623(8) Uani 1 1 d . . . C5 C 0.3638(2) -0.0050(3) 0.27804(16) 0.0802(9) Uani 1 1 d . . . H5 H 0.3686 -0.0759 0.3120 0.096 Uiso 1 1 calc R . . C6 C 0.3451(2) -0.0424(4) 0.20982(17) 0.0898(10) Uani 1 1 d . . . H6 H 0.3378 -0.1385 0.1978 0.108 Uiso 1 1 calc R . . C7 C 0.2267(2) 0.1711(3) 0.41966(13) 0.0610(7) Uani 1 1 d . . . C8 C 0.0653(2) 0.1822(4) 0.44485(18) 0.0897(10) Uani 1 1 d . . . H8A H 0.0334 0.2344 0.4811 0.108 Uiso 1 1 calc R . . H8B H 0.0734 0.0840 0.4607 0.108 Uiso 1 1 calc R . . C9 C 0.0076(3) 0.1818(4) 0.3786(3) 0.1297(17) Uani 1 1 d . . . H9A H -0.0006 0.2799 0.3626 0.156 Uiso 1 1 calc R . . H9B H 0.0393 0.1293 0.3423 0.156 Uiso 1 1 calc R . . C10 C -0.0807(3) 0.1165(5) 0.3900(3) 0.173(2) Uani 1 1 d . . . H10A H -0.0729 0.0220 0.4091 0.259 Uiso 1 1 calc R . . H10B H -0.1125 0.1100 0.3465 0.259 Uiso 1 1 calc R . . H10C H -0.1150 0.1745 0.4219 0.259 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S1 0.0711(5) 0.0563(5) 0.0856(6) -0.0052(4) -0.0091(4) -0.0001(4) Cl1 0.1665(11) 0.1463(10) 0.0640(6) 0.0033(6) 0.0064(5) 0.0066(7) N1 0.0790(16) 0.0418(12) 0.0828(16) -0.0109(12) 0.0037(13) -0.0052(13) N2 0.0812(18) 0.0496(13) 0.0780(17) -0.0056(12) 0.0128(13) 0.0023(14) O1 0.0740(15) 0.0752(14) 0.1296(19) -0.0132(13) -0.0070(12) -0.0170(11) O2 0.0959(15) 0.0670(13) 0.0860(14) -0.0017(12) -0.0214(12) 0.0210(12) O3 0.0877(15) 0.0421(12) 0.1044(16) -0.0030(11) 0.0108(11) -0.0002(10) C1 0.087(2) 0.088(2) 0.0604(19) 0.0083(18) 0.0107(16) 0.0040(19) C2 0.118(3) 0.087(3) 0.088(3) 0.035(2) -0.005(2) -0.011(2) C3 0.115(3) 0.059(2) 0.102(3) 0.012(2) -0.003(2) -0.0144(18) C4 0.0602(18) 0.0507(18) 0.0760(19) 0.0082(15) 0.0054(15) 0.0035(13) C5 0.115(3) 0.058(2) 0.067(2) 0.0062(16) 0.0070(18) 0.0164(17) C6 0.135(3) 0.066(2) 0.069(2) -0.0075(18) 0.012(2) 0.007(2) C7 0.085(2) 0.0449(17) 0.0530(16) -0.0030(14) 0.0001(14) 0.0023(17) C8 0.087(2) 0.080(2) 0.102(3) 0.000(2) 0.027(2) 0.005(2) C9 0.079(2) 0.085(2) 0.225(5) 0.066(3) -0.023(3) -0.023(2) C10 0.124(4) 0.105(3) 0.290(7) 0.050(4) -0.001(4) 0.003(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 O1 1.420(2) . ? S1 O2 1.421(2) . ? S1 N1 1.632(2) . ? S1 C4 1.759(3) . ? Cl1 C1 1.731(3) . ? N1 C7 1.388(3) . ? N1 H1 0.8600 . ? N2 C7 1.318(3) . ? N2 C8 1.454(4) . ? N2 H2 0.8600 . ? O3 C7 1.228(3) . ? C1 C6 1.346(4) . ? C1 C2 1.349(5) . ? C2 C3 1.382(5) . ? C2 H2A 0.9300 . ? C3 C4 1.372(4) . ? C3 H3 0.9300 . ? C4 C5 1.368(4) . ? C5 C6 1.383(4) . ? C5 H5 0.9300 . ? C6 H6 0.9300 . ? C8 C9 1.531(5) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 C10 1.454(6) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? 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 120.00(13) . . ? O1 S1 N1 103.53(13) . . ? O2 S1 N1 110.03(13) . . ? O1 S1 C4 108.66(14) . . ? O2 S1 C4 108.16(13) . . ? N1 S1 C4 105.53(13) . . ? C7 N1 S1 123.08(19) . . ? C7 N1 H1 118.5 . . ? S1 N1 H1 118.5 . . ? C7 N2 C8 122.5(2) . . ? C7 N2 H2 118.7 . . ? C8 N2 H2 118.7 . . ? C6 C1 C2 121.0(3) . . ? C6 C1 Cl1 118.9(3) . . ? C2 C1 Cl1 120.0(3) . . ? C1 C2 C3 119.7(3) . . ? C1 C2 H2A 120.2 . . ? C3 C2 H2A 120.2 . . ? C4 C3 C2 120.1(3) . . ? C4 C3 H3 119.9 . . ? C2 C3 H3 119.9 . . ? C5 C4 C3 119.2(3) . . ? C5 C4 S1 120.2(2) . . ? C3 C4 S1 120.6(2) . . ? C4 C5 C6 119.9(3) . . ? C4 C5 H5 120.0 . . ? C6 C5 H5 120.0 . . ? C1 C6 C5 120.0(3) . . ? C1 C6 H6 120.0 . . ? C5 C6 H6 120.0 . . ? O3 C7 N2 124.5(3) . . ? O3 C7 N1 120.9(3) . . ? N2 C7 N1 114.6(2) . . ? N2 C8 C9 112.6(3) . . ? N2 C8 H8A 109.1 . . ? C9 C8 H8A 109.1 . . ? N2 C8 H8B 109.1 . . ? C9 C8 H8B 109.1 . . ? H8A C8 H8B 107.8 . . ? C10 C9 C8 112.0(4) . . ? C10 C9 H9A 109.2 . . ? C8 C9 H9A 109.2 . . ? C10 C9 H9B 109.2 . . ? C8 C9 H9B 109.2 . . ? H9A C9 H9B 107.9 . . ? C9 C10 H10A 109.5 . . ? C9 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C9 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 S1 N1 C7 176.7(2) . . . . ? O2 S1 N1 C7 -53.8(3) . . . . ? C4 S1 N1 C7 62.6(2) . . . . ? C6 C1 C2 C3 0.4(6) . . . . ? Cl1 C1 C2 C3 -178.9(3) . . . . ? C1 C2 C3 C4 -0.8(5) . . . . ? C2 C3 C4 C5 0.6(5) . . . . ? C2 C3 C4 S1 -179.7(3) . . . . ? O1 S1 C4 C5 144.8(2) . . . . ? O2 S1 C4 C5 13.0(3) . . . . ? N1 S1 C4 C5 -104.7(3) . . . . ? O1 S1 C4 C3 -35.0(3) . . . . ? O2 S1 C4 C3 -166.7(2) . . . . ? N1 S1 C4 C3 75.5(3) . . . . ? C3 C4 C5 C6 0.1(5) . . . . ? S1 C4 C5 C6 -179.6(3) . . . . ? C2 C1 C6 C5 0.3(5) . . . . ? Cl1 C1 C6 C5 179.6(3) . . . . ? C4 C5 C6 C1 -0.5(5) . . . . ? C8 N2 C7 O3 2.4(4) . . . . ? C8 N2 C7 N1 -178.2(3) . . . . ? S1 N1 C7 O3 10.6(4) . . . . ? S1 N1 C7 N2 -168.79(19) . . . . ? C7 N2 C8 C9 -95.2(4) . . . . ? N2 C8 C9 C10 -179.9(3) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1 O3 0.86 1.95 2.736(3) 151.4 7_665 N2 H2 O2 0.86 2.40 3.124(3) 142.0 7_665 N2 H2 O3 0.86 2.56 3.270(3) 140.0 7_665 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.68 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.318 _refine_diff_density_min -0.245 _refine_diff_density_rms 0.043