#------------------------------------------------------------------------------ #$Date: 2025-08-19 11:43:10 +0100 (Tue, 19 Aug 2025) $ #$Revision: 301803 $ #$URL: svn://www.crystallography.net/cod/cif/2/20/50/2205032.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_2205032 loop_ _publ_author_name 'Xue, Gang' 'Yu, Wentao' 'Fang, Qi' _publ_section_title ; 4,5-Methylenedithio-1,3-dithiol-2-one ; _journal_issue 2 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o429 _journal_page_last o430 _journal_paper_doi 10.1107/S160053680500173X _journal_volume 61 _journal_year 2005 _chemical_formula_iupac 'C4 H2 O S4' _chemical_formula_moiety 'C4 H2 O S4' _chemical_formula_sum 'C4 H2 O S4' _chemical_formula_weight 194.30 _chemical_name_systematic ; 4,5-methylenedithio-1,3-dithiol-2-one ; _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 _audit_creation_method SHELXL-97 _cell_angle_alpha 90.00 _cell_angle_beta 97.586(7) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 7.8361(6) _cell_length_b 4.0090(3) _cell_length_c 21.572(2) _cell_measurement_reflns_used 39 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 15.630 _cell_measurement_theta_min 5.173 _cell_volume 671.75(10) _computing_cell_refinement XSCANS _computing_data_collection 'XSCANS (Bruker, 1996)' _computing_data_reduction XSCANS _computing_molecular_graphics SHELXTL _computing_publication_material SHELXTL _computing_structure_refinement 'SHELXTL (Bruker, 1997)' _computing_structure_solution 'SIR97 (Altomare et al., 1999)' _diffrn_ambient_temperature 293(2) _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.998 _diffrn_measurement_device_type 'Bruker P4' _diffrn_measurement_method \w _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 0.0234 _diffrn_reflns_av_sigmaI/netI 0.0201 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_h_min -1 _diffrn_reflns_limit_k_max 1 _diffrn_reflns_limit_k_min -5 _diffrn_reflns_limit_l_max 31 _diffrn_reflns_limit_l_min -31 _diffrn_reflns_number 3180 _diffrn_reflns_theta_full 31.00 _diffrn_reflns_theta_max 31.00 _diffrn_reflns_theta_min 2.62 _diffrn_standards_decay_% 0 _diffrn_standards_interval_count 97 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu 1.315 _exptl_absorpt_correction_T_max 0.5974 _exptl_absorpt_correction_T_min 0.4984 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_process_details '(XSCANS; Bruker, 1996)' _exptl_crystal_colour 'pale yellow' _exptl_crystal_density_diffrn 1.921 _exptl_crystal_density_method 'not measured' _exptl_crystal_description Prism _exptl_crystal_F_000 392 _exptl_crystal_size_max 0.52 _exptl_crystal_size_mid 0.44 _exptl_crystal_size_min 0.40 _refine_diff_density_max 0.328 _refine_diff_density_min -0.217 _refine_ls_extinction_coef 0.061(2) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method SHELXTL _refine_ls_goodness_of_fit_ref 1.040 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 83 _refine_ls_number_reflns 2140 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.040 _refine_ls_R_factor_all 0.0348 _refine_ls_R_factor_gt 0.0263 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w = 1/[\s^2^(Fo^2^)+(0.0336P)^2^+0.107P] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0634 _refine_ls_wR_factor_ref 0.0677 _reflns_number_gt 1763 _reflns_number_total 2140 _reflns_threshold_expression I>2\s(I) _cod_data_source_file ci6515.cif _cod_data_source_block I _cod_original_cell_volume 671.76(10) _cod_original_sg_symbol_H-M 'P 21/c' _cod_database_code 2205032 _cod_database_fobs_code 2205032 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 C1 0.48572(16) -0.2431(4) 0.39916(6) 0.0327(3) Uani d . 1 C C2 0.78742(15) 0.0298(4) 0.40420(5) 0.0271(3) Uani d . 1 C C3 0.72479(15) 0.0297(4) 0.34325(6) 0.0277(3) Uani d . 1 C C4 1.04694(17) 0.1291(4) 0.34732(6) 0.0333(3) Uani d . 1 C H1A 1.0881 -0.0974 0.3438 0.040 Uiso calc R 1 H H1B 1.1376 0.2810 0.3390 0.040 Uiso calc R 1 H O1 0.35729(13) -0.3809(4) 0.41068(5) 0.0488(3) Uani d . 1 O S1 0.66010(4) -0.13540(11) 0.456563(14) 0.03353(10) Uani d . 1 S S2 0.52008(4) -0.13009(11) 0.321867(15) 0.03450(11) Uani d . 1 S S3 0.99253(4) 0.20035(11) 0.425259(15) 0.03378(10) Uani d . 1 S S4 0.85669(4) 0.19662(11) 0.291205(15) 0.03372(10) Uani d . 1 S 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 C1 0.0250(6) 0.0391(8) 0.0337(6) -0.0045(6) 0.0032(5) 0.0000(6) C2 0.0209(5) 0.0344(7) 0.0260(5) -0.0022(5) 0.0032(4) -0.0016(5) C3 0.0227(5) 0.0338(7) 0.0267(5) -0.0016(5) 0.0035(4) 0.0005(5) C4 0.0246(6) 0.0395(8) 0.0369(6) -0.0002(5) 0.0078(5) 0.0020(6) O1 0.0311(5) 0.0651(9) 0.0501(6) -0.0174(5) 0.0057(4) 0.0039(6) S1 0.02571(15) 0.0496(2) 0.02553(15) -0.00561(14) 0.00428(11) 0.00187(14) S2 0.02594(16) 0.0478(2) 0.02835(16) -0.00737(14) -0.00171(11) -0.00140(14) S3 0.02395(15) 0.0452(2) 0.03138(17) -0.00721(14) 0.00056(12) -0.00437(15) S4 0.03096(17) 0.0423(2) 0.02861(16) -0.00157(15) 0.00640(12) 0.00607(14) 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' 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' 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 O1 C1 S1 123.84(11) y O1 C1 S2 122.96(11) y S1 C1 S2 113.20(7) y C3 C2 S1 118.08(10) y C3 C2 S3 117.33(10) y S1 C2 S3 124.59(7) y C2 C3 S2 117.86(10) y C2 C3 S4 117.16(10) y S2 C3 S4 124.97(7) y S3 C4 S4 108.83(7) y S3 C4 H1A 109.9 ? S4 C4 H1A 109.9 ? S3 C4 H1B 109.9 ? S4 C4 H1B 109.9 ? H1A C4 H1B 108.3 ? C2 S1 C1 95.44(6) y C3 S2 C1 95.38(6) y C2 S3 C4 91.04(6) y C3 S4 C4 91.02(6) y loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag C1 O1 1.2023(16) y C1 S1 1.7721(14) y C1 S2 1.7824(14) y C2 C3 1.3414(17) y C2 S1 1.7343(13) y C2 S3 1.7504(12) y C3 S2 1.7324(13) y C3 S4 1.7559(13) y C4 S3 1.8110(14) y C4 S4 1.8123(14) y C4 H1A 0.97 ? C4 H1B 0.97 ? 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 S1 C2 C3 S2 0.95(18) S3 C2 C3 S2 -178.65(7) S1 C2 C3 S4 -179.70(7) S3 C2 C3 S4 0.69(18) C3 C2 S1 C1 0.27(14) S3 C2 S1 C1 179.84(10) O1 C1 S1 C2 178.13(15) S2 C1 S1 C2 -1.32(10) C2 C3 S2 C1 -1.61(14) S4 C3 S2 C1 179.10(10) O1 C1 S2 C3 -177.75(15) S1 C1 S2 C3 1.70(10) C3 C2 S3 C4 -22.95(14) S1 C2 S3 C4 157.48(10) S4 C4 S3 C2 35.85(9) C2 C3 S4 C4 21.96(14) S2 C3 S4 C4 -158.75(10) S3 C4 S4 C3 -35.55(9) loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 ChemSpider 1552792 2 PubChem 2060090