#------------------------------------------------------------------------------ #$Date: 2025-08-19 11:43:10 +0100 (Tue, 19 Aug 2025) $ #$Revision: 301803 $ #$URL: svn://www.crystallography.net/cod/cif/2/20/49/2204955.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/. The original data for this entry # were provided by IUCr Journals, http://journals.iucr.org/. # # The file may be used within the scientific community so long as # proper attribution is given to the journal article from which the # data were obtained. # data_2204955 loop_ _publ_author_name 'Liang-Zhong Xu' 'Wei-Hua Li' 'Hai-Bin Song' 'Kai Li' 'Guan-ping Yu' _publ_section_title ; (4-Chlorobenzoyl)methyl morpholine-4-carbodithionate ; _journal_issue 1 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o130 _journal_page_last o131 _journal_paper_doi 10.1107/S1600536804032593 _journal_volume 61 _journal_year 2005 _chemical_formula_iupac 'C13 H14 Cl N O2 S2' _chemical_formula_moiety 'C13 H14 Cl N O2 S2' _chemical_formula_sum 'C13 H14 Cl N O2 S2' _chemical_formula_weight 315.82 _chemical_name_systematic ; (4-Chlorobenzoyl)methyl morpholine-4-carbodithionate ; _space_group_IT_number 14 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_space_group_name_H-M 'P 1 21/c 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _cell_angle_alpha 90.00 _cell_angle_beta 100.127(8) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 18.092(5) _cell_length_b 9.471(2) _cell_length_c 8.464(2) _cell_measurement_reflns_used 967 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 25.65 _cell_measurement_theta_min 3.14 _cell_volume 1427.7(6) _computing_cell_refinement SMART _computing_data_collection 'SMART (Bruker, 1998)' _computing_data_reduction 'SAINT (Bruker, 1999)' _computing_molecular_graphics 'SHELXTL (Bruker, 1999)' _computing_publication_material SHELXTL _computing_structure_refinement SHELXL97 _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _diffrn_ambient_temperature 293(2) _diffrn_measured_fraction_theta_full 0.991 _diffrn_measured_fraction_theta_max 0.991 _diffrn_measurement_device_type 'Bruker CCD area-detector' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0299 _diffrn_reflns_av_sigmaI/netI 0.0356 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_l_max 6 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_number 7932 _diffrn_reflns_theta_full 26.29 _diffrn_reflns_theta_max 26.29 _diffrn_reflns_theta_min 2.29 _diffrn_standards_decay_% 0 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.556 _exptl_absorpt_correction_T_max 0.837 _exptl_absorpt_correction_T_min 0.761 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SADABS; Sheldrick, 1996)' _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.469 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 656 _exptl_crystal_size_max 0.48 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.32 _refine_diff_density_max 0.212 _refine_diff_density_min -0.207 _refine_ls_extinction_coef 0.0260(16) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method SHELXL97 _refine_ls_goodness_of_fit_ref 1.059 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 173 _refine_ls_number_reflns 2876 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.059 _refine_ls_R_factor_all 0.0566 _refine_ls_R_factor_gt 0.0348 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0352P)^2^+0.3711P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0783 _refine_ls_wR_factor_ref 0.0882 _reflns_number_gt 2096 _reflns_number_total 2876 _reflns_threshold_expression I>2\s(I) _cod_data_source_file rz6026.cif _cod_data_source_block I _cod_depositor_comments ; The following automatic conversions were performed: '_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic' according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29. Automatic conversion script Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius The following automatic conversions were performed: '_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic' according to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29. Automatic conversion script Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana ; _cod_original_sg_symbol_H-M P21/c _cod_database_code 2204955 _cod_database_fobs_code 2204955 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' loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_occupancy _atom_site_type_symbol S1 0.16030(3) 0.14930(6) 0.03531(7) 0.04738(18) Uani d . 1 S S2 0.27562(3) -0.06895(7) -0.00865(8) 0.0565(2) Uani d . 1 S Cl1 0.53881(3) 0.06809(7) 0.79598(9) 0.0723(2) Uani d . 1 Cl N1 0.14149(9) -0.04118(17) -0.1929(2) 0.0411(4) Uani d . 1 N O1 0.02319(8) -0.19058(15) -0.38685(18) 0.0525(4) Uani d . 1 O O2 0.19713(8) -0.00085(18) 0.34967(19) 0.0582(4) Uani d . 1 O C1 0.06841(12) 0.0265(2) -0.2517(3) 0.0535(6) Uani d . 1 C H1A 0.0704 0.0766 -0.3508 0.064 Uiso calc R 1 H H1B 0.0574 0.0943 -0.1732 0.064 Uiso calc R 1 H C2 0.00735(12) -0.0839(2) -0.2805(3) 0.0548(6) Uani d . 1 C H2A 0.0020 -0.1265 -0.1789 0.066 Uiso calc R 1 H H2B -0.0399 -0.0389 -0.3250 0.066 Uiso calc R 1 H C3 0.09146(11) -0.2594(2) -0.3188(3) 0.0490(5) Uani d . 1 C H3A 0.1011 -0.3358 -0.3888 0.059 Uiso calc R 1 H H3B 0.0863 -0.2999 -0.2160 0.059 Uiso calc R 1 H C4 0.15671(11) -0.1589(2) -0.2956(3) 0.0465(5) Uani d . 1 C H4A 0.2020 -0.2078 -0.2461 0.056 Uiso calc R 1 H H4B 0.1644 -0.1230 -0.3989 0.056 Uiso calc R 1 H C5 0.19172(10) 0.0028(2) -0.0669(2) 0.0365(4) Uani d . 1 C C6 0.23949(12) 0.1798(2) 0.1901(2) 0.0465(5) Uani d . 1 C H6A 0.2846 0.1759 0.1431 0.056 Uiso calc R 1 H H6B 0.2358 0.2745 0.2316 0.056 Uiso calc R 1 H C7 0.24806(11) 0.0767(2) 0.3296(2) 0.0416(5) Uani d . 1 C C8 0.32085(11) 0.0779(2) 0.4432(2) 0.0394(5) Uani d . 1 C C9 0.33625(12) -0.0298(2) 0.5547(3) 0.0539(6) Uani d . 1 C H9 0.3011 -0.1013 0.5561 0.065 Uiso calc R 1 H C10 0.40263(13) -0.0333(3) 0.6638(3) 0.0610(7) Uani d . 1 C H10 0.4122 -0.1061 0.7383 0.073 Uiso calc R 1 H C11 0.45447(12) 0.0726(2) 0.6607(3) 0.0501(5) Uani d . 1 C C12 0.44071(12) 0.1813(2) 0.5518(3) 0.0539(6) Uani d . 1 C H12 0.4760 0.2527 0.5513 0.065 Uiso calc R 1 H C13 0.37416(12) 0.1836(2) 0.4435(3) 0.0483(5) Uani d . 1 C H13 0.3648 0.2570 0.3696 0.058 Uiso calc R 1 H loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 S1 0.0532(3) 0.0416(3) 0.0463(3) 0.0042(2) 0.0059(2) -0.0042(3) S2 0.0361(3) 0.0628(4) 0.0660(4) 0.0068(3) -0.0039(3) -0.0116(3) Cl1 0.0537(4) 0.0825(5) 0.0750(5) 0.0037(3) -0.0046(3) -0.0142(4) N1 0.0382(9) 0.0387(9) 0.0439(10) 0.0036(7) 0.0001(8) -0.0036(8) O1 0.0434(8) 0.0526(9) 0.0559(9) 0.0013(7) -0.0066(7) -0.0091(7) O2 0.0519(9) 0.0636(10) 0.0584(10) -0.0213(8) 0.0076(7) 0.0101(8) C1 0.0532(13) 0.0429(12) 0.0570(14) 0.0109(10) -0.0110(11) -0.0021(11) C2 0.0380(11) 0.0615(15) 0.0606(15) 0.0097(10) -0.0031(11) -0.0054(12) C3 0.0476(12) 0.0432(12) 0.0539(13) 0.0040(10) 0.0024(10) -0.0082(10) C4 0.0414(11) 0.0545(13) 0.0435(12) 0.0021(10) 0.0074(9) -0.0095(10) C5 0.0378(10) 0.0346(10) 0.0372(11) -0.0031(8) 0.0071(9) 0.0037(9) C6 0.0569(13) 0.0409(12) 0.0422(12) -0.0092(10) 0.0097(10) -0.0053(9) C7 0.0475(12) 0.0375(11) 0.0423(12) -0.0054(9) 0.0151(10) -0.0056(9) C8 0.0411(11) 0.0372(11) 0.0429(11) -0.0042(9) 0.0152(9) -0.0041(9) C9 0.0462(12) 0.0461(13) 0.0702(16) -0.0073(10) 0.0120(11) 0.0099(12) C10 0.0527(14) 0.0544(14) 0.0738(17) 0.0021(11) 0.0060(13) 0.0147(13) C11 0.0439(12) 0.0555(14) 0.0514(13) 0.0026(10) 0.0094(10) -0.0121(11) C12 0.0489(13) 0.0538(14) 0.0601(15) -0.0182(10) 0.0120(11) -0.0108(12) C13 0.0566(13) 0.0428(12) 0.0467(13) -0.0106(10) 0.0125(11) -0.0003(10) 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' Cl Cl 0.1484 0.1585 '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' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_publ_flag C5 S1 C6 101.47(10) yes C5 N1 C4 122.38(16) ? C5 N1 C1 125.12(17) ? C4 N1 C1 112.36(16) yes C2 O1 C3 109.12(15) yes N1 C1 C2 109.95(17) ? N1 C1 H1A 109.7 ? C2 C1 H1A 109.7 ? N1 C1 H1B 109.7 ? C2 C1 H1B 109.7 ? H1A C1 H1B 108.2 ? O1 C2 C1 111.88(18) ? O1 C2 H2A 109.2 ? C1 C2 H2A 109.2 ? O1 C2 H2B 109.2 ? C1 C2 H2B 109.2 ? H2A C2 H2B 107.9 ? O1 C3 C4 111.60(18) ? O1 C3 H3A 109.3 ? C4 C3 H3A 109.3 ? O1 C3 H3B 109.3 ? C4 C3 H3B 109.3 ? H3A C3 H3B 108.0 ? N1 C4 C3 109.47(16) ? N1 C4 H4A 109.8 ? C3 C4 H4A 109.8 ? N1 C4 H4B 109.8 ? C3 C4 H4B 109.8 ? H4A C4 H4B 108.2 ? N1 C5 S2 124.50(15) ? N1 C5 S1 113.54(14) yes S2 C5 S1 121.95(11) ? C7 C6 S1 115.17(14) ? C7 C6 H6A 108.5 ? S1 C6 H6A 108.5 ? C7 C6 H6B 108.5 ? S1 C6 H6B 108.5 ? H6A C6 H6B 107.5 ? O2 C7 C8 121.44(19) ? O2 C7 C6 121.46(19) ? C8 C7 C6 117.08(16) ? C9 C8 C13 118.2(2) ? C9 C8 C7 118.96(17) ? C13 C8 C7 122.79(19) ? C10 C9 C8 121.4(2) ? C10 C9 H9 119.3 ? C8 C9 H9 119.3 ? C11 C10 C9 119.0(2) ? C11 C10 H10 120.5 ? C9 C10 H10 120.5 ? C12 C11 C10 121.0(2) ? C12 C11 Cl1 119.59(17) ? C10 C11 Cl1 119.43(19) ? C11 C12 C13 119.4(2) ? C11 C12 H12 120.3 ? C13 C12 H12 120.3 ? C12 C13 C8 120.9(2) ? C12 C13 H13 119.5 ? C8 C13 H13 119.5 ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag S1 C5 1.780(2) yes S1 C6 1.787(2) yes S2 C5 1.657(2) yes Cl1 C11 1.740(2) yes N1 C5 1.341(2) yes N1 C4 1.469(3) yes N1 C1 1.475(2) yes O1 C2 1.416(3) yes O1 C3 1.426(2) yes O2 C7 1.214(2) no C1 C2 1.509(3) no C1 H1A 0.9700 no C1 H1B 0.9700 no C2 H2A 0.9700 no C2 H2B 0.9700 no C3 C4 1.502(3) yes C3 H3A 0.9700 no C3 H3B 0.9700 no C4 H4A 0.9700 no C4 H4B 0.9700 no C6 C7 1.518(3) no C6 H6A 0.9700 no C6 H6B 0.9700 no C7 C8 1.488(3) no C8 C9 1.384(3) no C8 C13 1.390(3) no C9 C10 1.381(3) no C9 H9 0.9300 no C10 C11 1.376(3) no C10 H10 0.9300 no C11 C12 1.375(3) no C12 C13 1.380(3) no C12 H12 0.9300 no C13 H13 0.9300 no loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_publ_flag C1 H1B S1 ? 0.97 2.39 2.932(3) 115 yes C4 H4A S2 ? 0.97 2.57 3.068(3) 112 yes C4 H4B O2 1_554 0.97 2.58 3.544(4) 172 yes C6 H6A S2 ? 0.97 2.64 3.032(2) 104 yes 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 C5 N1 C1 C2 -132.8(2) C4 N1 C1 C2 51.4(2) C3 O1 C2 C1 60.7(2) N1 C1 C2 O1 -55.6(2) C2 O1 C3 C4 -61.9(2) C5 N1 C4 C3 131.7(2) C1 N1 C4 C3 -52.3(2) O1 C3 C4 N1 57.6(2) C4 N1 C5 S2 -0.9(3) C1 N1 C5 S2 -176.38(17) C4 N1 C5 S1 178.80(15) C1 N1 C5 S1 3.4(3) C6 S1 C5 N1 -179.36(14) C6 S1 C5 S2 0.38(15) C5 S1 C6 C7 -76.62(17) S1 C6 C7 O2 -14.4(3) S1 C6 C7 C8 167.25(14) O2 C7 C8 C9 13.0(3) C6 C7 C8 C9 -168.71(19) O2 C7 C8 C13 -166.4(2) C6 C7 C8 C13 11.9(3) C13 C8 C9 C10 0.0(3) C7 C8 C9 C10 -179.4(2) C8 C9 C10 C11 -0.2(4) C9 C10 C11 C12 0.5(4) C9 C10 C11 Cl1 -179.19(19) C10 C11 C12 C13 -0.4(3) Cl1 C11 C12 C13 179.22(17) C11 C12 C13 C8 0.2(3) C9 C8 C13 C12 0.1(3) C7 C8 C13 C12 179.43(19) loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 ChemSpider 608837 2 PubChem 698733