data_global _journal_name_full 'Green Chemistry' _journal_coden_Cambridge 1048 _publ_contact_author_name 'Bhisma Patel' _publ_contact_author_email PATEL@IITG.ERNET.IN _publ_section_title ; It is "4-thiazolidinone" and not thiohydantoin as the reaction product of 1,3-disubstituted thiourea and chloroacetylchloride ; loop_ _publ_author_name 'Bhisma Patel' 'Harisadhan Ghosh' 'Ramesh Yella' # Attachment '1a.CIF' data_ry1-125 _database_code_depnum_ccdc_archive 'CCDC 686655' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point 178 _chemical_formula_moiety 'C15 H12 N2 O S' _chemical_formula_sum 'C15 H12 N2 O S' _chemical_formula_weight 268.33 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P b c a' _symmetry_space_group_name_Hall '-P 2ac 2ab ' _symmetry_int_tables_number 61 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 10.9047(2) _cell_length_b 10.0696(2) _cell_length_c 24.2827(6) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2666.39(10) _cell_formula_units_Z 8 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 4275 _cell_measurement_theta_min 0.00 _cell_measurement_theta_max 0.00 _exptl_crystal_description block _exptl_crystal_colour brown _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.1 _exptl_crystal_size_min 0.1 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.337 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1120 _exptl_absorpt_coefficient_mu 0.235 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_probe ? _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 21603 _diffrn_reflns_av_R_equivalents 0.0572 _diffrn_reflns_av_sigmaI/netI 0.0348 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -32 _diffrn_reflns_limit_l_max 32 _diffrn_reflns_theta_min 1.68 _diffrn_reflns_theta_max 28.32 _reflns_number_total 3281 _reflns_number_gt 2215 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0481P)^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 SHELXL _refine_ls_extinction_coef 0.0006(4) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3281 _refine_ls_number_parameters 173 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0566 _refine_ls_R_factor_gt 0.0344 _refine_ls_wR_factor_ref 0.0930 _refine_ls_wR_factor_gt 0.0860 _refine_ls_goodness_of_fit_ref 0.947 _refine_ls_restrained_S_all 0.947 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S1 S 0.91859(3) 1.09078(3) 0.435275(16) 0.04969(14) Uani 1 1 d . . . O1 O 0.78124(10) 0.77402(10) 0.49934(4) 0.0593(3) Uani 1 1 d . . . N2 N 0.90466(9) 0.83248(10) 0.42707(4) 0.0420(3) Uani 1 1 d . . . N1 N 1.01888(11) 0.93033(11) 0.35660(5) 0.0499(3) Uani 1 1 d . . . C4 C 0.92560(12) 0.69801(13) 0.40863(6) 0.0419(3) Uani 1 1 d . . . C15 C 0.95563(12) 0.94248(12) 0.40000(6) 0.0403(3) Uani 1 1 d . . . C13 C 0.83061(12) 0.85842(14) 0.47196(6) 0.0432(3) Uani 1 1 d . . . C7 C 1.06728(13) 1.04826(14) 0.33237(6) 0.0480(3) Uani 1 1 d . . . C14 C 0.81631(13) 1.00497(13) 0.48134(6) 0.0461(3) Uani 1 1 d . . . H14A H 0.8361 1.0267 0.5192 0.055 Uiso 1 1 calc R . . H14B H 0.7323 1.0316 0.4743 0.055 Uiso 1 1 calc R . . C5 C 1.01028(14) 0.62045(15) 0.43511(7) 0.0564(4) Uani 1 1 d . . . H5 H 1.0577 0.6556 0.4634 0.068 Uiso 1 1 calc R . . C3 C 0.85631(15) 0.64873(16) 0.36595(6) 0.0561(4) Uani 1 1 d . . . H3 H 0.7997 0.7025 0.3480 0.067 Uiso 1 1 calc R . . C10 C 1.16680(19) 1.27063(17) 0.28244(7) 0.0759(5) Uani 1 1 d . . . H10 H 1.2003 1.3453 0.2657 0.091 Uiso 1 1 calc R . . C6 C 1.02459(16) 0.48906(16) 0.41936(8) 0.0668(5) Uani 1 1 d . . . H6 H 1.0808 0.4352 0.4376 0.080 Uiso 1 1 calc R . . C8 C 1.00560(15) 1.11166(15) 0.29051(6) 0.0585(4) Uani 1 1 d . . . H8 H 0.9300 1.0794 0.2788 0.070 Uiso 1 1 calc R . . C1 C 0.95590(18) 0.43840(16) 0.37695(8) 0.0700(5) Uani 1 1 d . . . H1 H 0.9660 0.3503 0.3663 0.084 Uiso 1 1 calc R . . C12 C 1.18006(16) 1.09661(17) 0.34892(7) 0.0708(5) Uani 1 1 d . . . H12 H 1.2233 1.0543 0.3769 0.085 Uiso 1 1 calc R . . C2 C 0.87233(19) 0.51715(17) 0.35012(7) 0.0715(5) Uani 1 1 d . . . H2 H 0.8263 0.4824 0.3213 0.086 Uiso 1 1 calc R . . C9 C 1.05520(18) 1.22293(17) 0.26573(7) 0.0702(5) Uani 1 1 d . . . H9 H 1.0127 1.2655 0.2376 0.084 Uiso 1 1 calc R . . C11 C 1.22851(17) 1.2082(2) 0.32376(9) 0.0850(6) Uani 1 1 d . . . H11 H 1.3041 1.2409 0.3352 0.102 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 0.0580(2) 0.02848(19) 0.0626(3) 0.00032(16) 0.00481(18) -0.00011(15) O1 0.0703(7) 0.0408(6) 0.0668(7) -0.0011(5) 0.0218(5) -0.0105(5) N2 0.0489(6) 0.0270(6) 0.0502(7) -0.0005(5) 0.0068(5) -0.0017(5) N1 0.0586(7) 0.0366(7) 0.0545(7) 0.0022(5) 0.0086(6) -0.0048(5) C4 0.0473(8) 0.0284(7) 0.0500(8) 0.0001(6) 0.0102(6) -0.0036(6) C15 0.0409(7) 0.0315(7) 0.0486(8) 0.0020(6) -0.0028(6) -0.0004(5) C13 0.0438(7) 0.0354(7) 0.0503(8) -0.0025(6) 0.0016(6) -0.0012(6) C7 0.0578(9) 0.0374(7) 0.0488(8) 0.0000(6) 0.0099(7) -0.0035(7) C14 0.0511(8) 0.0342(7) 0.0531(8) -0.0021(6) 0.0043(6) 0.0044(6) C5 0.0551(9) 0.0415(8) 0.0726(10) -0.0021(7) -0.0025(8) 0.0006(7) C3 0.0725(10) 0.0447(9) 0.0511(9) -0.0011(7) -0.0011(8) -0.0021(8) C10 0.1043(15) 0.0536(11) 0.0700(12) 0.0089(9) 0.0288(11) -0.0176(11) C6 0.0704(10) 0.0393(9) 0.0907(13) 0.0038(9) 0.0115(10) 0.0118(8) C8 0.0704(10) 0.0499(9) 0.0551(10) 0.0003(7) -0.0001(8) -0.0045(8) C1 0.1005(13) 0.0349(8) 0.0747(12) -0.0074(8) 0.0334(11) -0.0011(9) C12 0.0658(10) 0.0713(12) 0.0752(11) 0.0204(9) -0.0063(9) -0.0173(9) C2 0.1079(14) 0.0507(10) 0.0558(10) -0.0130(8) 0.0027(10) -0.0157(10) C9 0.1052(15) 0.0522(10) 0.0531(10) 0.0093(8) 0.0076(9) 0.0025(10) C11 0.0766(12) 0.0777(13) 0.1009(15) 0.0109(12) 0.0051(11) -0.0318(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 C15 1.7683(13) . ? S1 C14 1.8005(14) . ? O1 C13 1.2060(16) . ? N2 C13 1.3814(16) . ? N2 C15 1.4029(16) . ? N2 C4 1.4443(16) . ? N1 C15 1.2655(17) . ? N1 C7 1.4265(17) . ? C4 C5 1.370(2) . ? C4 C3 1.375(2) . ? C13 C14 1.5013(19) . ? C7 C8 1.376(2) . ? C7 C12 1.382(2) . ? C5 C6 1.386(2) . ? C3 C2 1.391(2) . ? C10 C11 1.362(3) . ? C10 C9 1.370(3) . ? C6 C1 1.372(3) . ? C8 C9 1.382(2) . ? C1 C2 1.372(2) . ? C12 C11 1.384(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 C15 S1 C14 92.13(6) . . ? C13 N2 C15 116.87(11) . . ? C13 N2 C4 120.95(11) . . ? C15 N2 C4 122.17(11) . . ? C15 N1 C7 117.69(12) . . ? C5 C4 C3 121.23(14) . . ? C5 C4 N2 119.71(13) . . ? C3 C4 N2 119.02(12) . . ? N1 C15 N2 121.99(12) . . ? N1 C15 S1 127.56(10) . . ? N2 C15 S1 110.45(9) . . ? O1 C13 N2 124.25(13) . . ? O1 C13 C14 124.24(12) . . ? N2 C13 C14 111.49(11) . . ? C8 C7 C12 119.10(14) . . ? C8 C7 N1 120.67(13) . . ? C12 C7 N1 120.16(14) . . ? C13 C14 S1 108.25(9) . . ? C4 C5 C6 119.39(15) . . ? C4 C3 C2 118.88(15) . . ? C11 C10 C9 119.69(17) . . ? C1 C6 C5 120.03(16) . . ? C7 C8 C9 120.43(16) . . ? C6 C1 C2 120.27(15) . . ? C7 C12 C11 119.81(17) . . ? C1 C2 C3 120.18(16) . . ? C10 C9 C8 120.20(17) . . ? C10 C11 C12 120.76(17) . . ? _diffrn_measured_fraction_theta_max 0.987 _diffrn_reflns_theta_full 28.32 _diffrn_measured_fraction_theta_full 0.987 _refine_diff_density_max 0.168 _refine_diff_density_min -0.198 _refine_diff_density_rms 0.031 _chemical_compound_source synthesized _exptl_crystal_recrystallization_method Chloroform-hexane # Attachment '5a.cif' data_ry1-168a _database_code_depnum_ccdc_archive 'CCDC 692011' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C15 H10 Cl2 N2 O S' _chemical_formula_sum 'C15 H10 Cl2 N2 O S' _chemical_formula_weight 337.21 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 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 12.900(4) _cell_length_b 10.035(4) _cell_length_c 24.251(8) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3139.2(18) _cell_formula_units_Z 8 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 3584 _cell_measurement_theta_min 0.00 _cell_measurement_theta_max 0.00 _exptl_crystal_description block _exptl_crystal_colour brown _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.43 _exptl_crystal_size_min 0.40 _exptl_crystal_density_meas 1.425 _exptl_crystal_density_diffrn 1.427 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1376 _exptl_absorpt_coefficient_mu 0.545 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 16750 _diffrn_reflns_av_R_equivalents 0.0463 _diffrn_reflns_av_sigmaI/netI 0.0524 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 31 _diffrn_reflns_theta_min 1.68 _diffrn_reflns_theta_max 27.91 _reflns_number_total 3513 _reflns_number_gt 1684 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.1050P)^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 3513 _refine_ls_number_parameters 190 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1194 _refine_ls_R_factor_gt 0.0576 _refine_ls_wR_factor_ref 0.1953 _refine_ls_wR_factor_gt 0.1633 _refine_ls_goodness_of_fit_ref 0.970 _refine_ls_restrained_S_all 0.970 _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 0.42690(7) 1.04798(9) 0.56995(4) 0.0655(3) Uani 1 1 d . . . Cl1 Cl 0.41298(7) 1.05185(10) 0.73448(5) 0.0855(4) Uani 1 1 d . . . Cl2 Cl 0.58150(7) 0.64170(11) 0.54036(5) 0.0932(4) Uani 1 1 d . . . N2 N 0.39712(19) 0.7899(3) 0.58347(12) 0.0585(7) Uani 1 1 d . . . N1 N 0.5176(2) 0.8814(3) 0.64658(12) 0.0665(8) Uani 1 1 d . . . O1 O 0.2851(2) 0.7340(3) 0.51303(12) 0.0961(10) Uani 1 1 d . . . C1 C 0.4078(2) 0.6532(4) 0.60432(15) 0.0633(9) Uani 1 1 d . . . C10 C 0.5753(2) 0.9953(3) 0.66498(14) 0.0561(9) Uani 1 1 d . . . C9 C 0.4560(2) 0.8978(3) 0.60564(15) 0.0580(8) Uani 1 1 d . . . C12 C 0.5932(3) 1.1889(3) 0.72587(15) 0.0671(10) Uani 1 1 d . . . H12 H 0.5659 1.2429 0.7534 0.081 Uiso 1 1 calc R . . C11 C 0.5369(2) 1.0813(3) 0.70628(15) 0.0600(9) Uani 1 1 d . . . C8 C 0.3344(3) 0.9645(3) 0.52407(16) 0.0681(10) Uani 1 1 d . . . H8A H 0.2656 1.0013 0.5293 0.082 Uiso 1 1 calc R . . H8B H 0.3544 0.9777 0.4859 0.082 Uiso 1 1 calc R . . C7 C 0.3343(3) 0.8180(3) 0.53766(15) 0.0639(9) Uani 1 1 d . . . C6 C 0.4900(3) 0.5764(4) 0.58501(15) 0.0685(10) Uani 1 1 d . . . C2 C 0.3274(3) 0.6047(3) 0.64055(15) 0.0704(10) Uani 1 1 d . . . H2 H 0.2714 0.6564 0.6518 0.085 Uiso 1 1 calc R . . C4 C 0.4240(4) 0.3937(5) 0.6390(2) 0.0910(14) Uani 1 1 d . . . H4 H 0.4285 0.3058 0.6510 0.109 Uiso 1 1 calc R . . C15 C 0.6735(3) 1.0221(4) 0.64394(16) 0.0753(11) Uani 1 1 d . . . H15 H 0.7016 0.9663 0.6172 0.090 Uiso 1 1 calc R . . C13 C 0.6906(3) 1.2155(4) 0.70413(17) 0.0796(11) Uani 1 1 d . . . H13 H 0.7287 1.2877 0.7171 0.095 Uiso 1 1 calc R . . C3 C 0.3417(4) 0.4708(5) 0.65738(17) 0.0921(13) Uani 1 1 d . . . H3 H 0.2942 0.4332 0.6817 0.111 Uiso 1 1 calc R . . C5 C 0.4991(4) 0.4408(4) 0.60405(19) 0.0865(13) Uani 1 1 d . . . H5 H 0.5541 0.3871 0.5930 0.104 Uiso 1 1 calc R . . C14 C 0.7312(3) 1.1337(5) 0.66275(16) 0.0806(12) Uani 1 1 d . . . H14 H 0.7959 1.1523 0.6476 0.097 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 0.0749(6) 0.0476(5) 0.0739(7) 0.0038(4) -0.0120(5) 0.0001(4) Cl1 0.0714(7) 0.0855(8) 0.0994(9) 0.0020(6) 0.0140(5) -0.0027(5) Cl2 0.0797(7) 0.0968(9) 0.1031(9) -0.0117(7) 0.0151(5) 0.0079(5) N2 0.0682(16) 0.0386(15) 0.0685(19) 0.0032(13) -0.0168(14) 0.0018(12) N1 0.0717(19) 0.0546(18) 0.073(2) -0.0027(15) -0.0202(16) 0.0041(14) O1 0.111(2) 0.0671(17) 0.111(2) 0.0140(16) -0.0579(18) -0.0165(14) C1 0.062(2) 0.063(2) 0.065(2) -0.0068(19) -0.0199(17) 0.0007(16) C10 0.058(2) 0.0447(18) 0.066(2) 0.0042(17) -0.0153(16) 0.0002(15) C9 0.0559(19) 0.0479(19) 0.070(2) -0.0075(17) -0.0035(18) 0.0037(15) C12 0.078(2) 0.057(2) 0.066(2) -0.0063(19) -0.0113(18) 0.0007(18) C11 0.0539(19) 0.056(2) 0.070(2) 0.0033(18) -0.0078(18) 0.0021(15) C8 0.070(2) 0.059(2) 0.075(2) 0.0059(18) -0.0168(19) 0.0088(17) C7 0.0601(19) 0.054(2) 0.077(2) 0.0028(19) -0.0153(18) 0.0008(17) C6 0.066(2) 0.069(3) 0.071(3) -0.0085(19) -0.0144(18) 0.0018(18) C2 0.094(3) 0.054(2) 0.064(2) 0.0141(18) -0.010(2) -0.0214(19) C4 0.109(4) 0.063(3) 0.100(3) 0.009(3) -0.031(3) 0.005(3) C15 0.070(2) 0.083(3) 0.073(2) -0.007(2) -0.006(2) 0.011(2) C13 0.081(3) 0.077(3) 0.081(3) 0.002(2) -0.015(2) -0.019(2) C3 0.104(3) 0.088(3) 0.084(3) 0.010(2) -0.011(2) -0.020(3) C5 0.098(3) 0.064(3) 0.098(3) -0.009(2) -0.032(3) 0.009(2) C14 0.062(2) 0.099(3) 0.081(3) 0.006(3) -0.005(2) -0.015(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 C9 1.778(3) . ? S1 C8 1.834(3) . ? Cl1 C11 1.764(3) . ? Cl2 C6 1.730(4) . ? N2 C7 1.404(4) . ? N2 C9 1.427(4) . ? N2 C1 1.468(4) . ? N1 C9 1.283(4) . ? N1 C10 1.435(4) . ? O1 C7 1.212(4) . ? C1 C6 1.392(5) . ? C1 C2 1.444(5) . ? C10 C15 1.391(5) . ? C10 C11 1.412(5) . ? C12 C11 1.385(5) . ? C12 C13 1.389(5) . ? C8 C7 1.506(4) . ? C6 C5 1.442(5) . ? C2 C3 1.416(5) . ? C4 C5 1.372(6) . ? C4 C3 1.387(6) . ? C15 C14 1.420(6) . ? C13 C14 1.399(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 C9 S1 C8 92.60(15) . . ? C7 N2 C9 116.9(3) . . ? C7 N2 C1 121.0(3) . . ? C9 N2 C1 121.9(3) . . ? C9 N1 C10 117.4(3) . . ? C6 C1 C2 124.4(3) . . ? C6 C1 N2 118.2(3) . . ? C2 C1 N2 117.2(3) . . ? C15 C10 C11 117.5(3) . . ? C15 C10 N1 120.8(3) . . ? C11 C10 N1 121.7(3) . . ? N1 C9 N2 121.6(3) . . ? N1 C9 S1 128.0(3) . . ? N2 C9 S1 110.3(2) . . ? C11 C12 C13 119.6(3) . . ? C12 C11 C10 122.4(3) . . ? C12 C11 Cl1 118.2(3) . . ? C10 C11 Cl1 119.4(3) . . ? C7 C8 S1 108.3(2) . . ? O1 C7 N2 123.5(3) . . ? O1 C7 C8 124.9(3) . . ? N2 C7 C8 111.6(3) . . ? C1 C6 C5 118.5(4) . . ? C1 C6 Cl2 121.4(3) . . ? C5 C6 Cl2 120.1(3) . . ? C3 C2 C1 113.7(4) . . ? C5 C4 C3 123.1(4) . . ? C10 C15 C14 120.8(4) . . ? C12 C13 C14 119.9(4) . . ? C4 C3 C2 122.5(4) . . ? C4 C5 C6 117.8(4) . . ? C13 C14 C15 119.8(4) . . ? _diffrn_measured_fraction_theta_max 0.935 _diffrn_reflns_theta_full 27.91 _diffrn_measured_fraction_theta_full 0.98 _refine_diff_density_max 0.391 _refine_diff_density_min -0.480 _refine_diff_density_rms 0.061