#------------------------------------------------------------------------------ #$Date: 2013-12-28 13:58:47 +0000 (Sat, 28 Dec 2013) $ #$Revision: 91933 $ #$URL: svn://www.crystallography.net/cod/cif/2/20/21/2202112.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_2202112 loop_ _publ_author_name 'Qingjian Liu' 'Daqing Shi' 'Kaibei Yu' 'Jianhua Xu' _publ_section_title ; 1,1'-(1,2-Ethanediyl)bis(2,3-dihydro-3-methyl-1H-imidazole-2-thione) ; _journal_issue 3 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o356 _journal_page_last o357 _journal_volume 59 _journal_year 2003 _chemical_formula_iupac 'C10 H14 N4 S2' _chemical_formula_moiety 'C10 H14 N4 S2' _chemical_formula_sum 'C10 H14 N4 S2' _chemical_formula_weight 254.37 _chemical_melting_point 467.8(8) _chemical_name_systematic ; 1,1'-(1,2-Ethanediyl)bis(2,3-dihydro-3-methyl-1H-imidazole-2-thione) ; _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 107.080(10) _cell_angle_gamma 90.00 _cell_formula_units_Z 2 _cell_length_a 4.6670(10) _cell_length_b 19.720(3) _cell_length_c 7.0370(10) _cell_measurement_reflns_used 27 _cell_measurement_temperature 288(2) _cell_measurement_theta_max 13.56 _cell_measurement_theta_min 4.80 _cell_volume 619.07(19) _computing_cell_refinement XSCANS _computing_data_collection 'XSCANS (Siemens, 1994)' _computing_data_reduction 'SHELXTL (Sheldrick, 1997)' _computing_molecular_graphics SHELXTL _computing_publication_material SHELXTL _computing_structure_refinement SHELXTL _computing_structure_solution SHELXTL _diffrn_ambient_temperature 288(2) _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 1.000 _diffrn_measurement_device_type 'Siemens P4' _diffrn_measurement_method \w _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'normal-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0293 _diffrn_reflns_av_sigmaI/netI 0.0388 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_number 1339 _diffrn_reflns_theta_full 25.00 _diffrn_reflns_theta_max 25.00 _diffrn_reflns_theta_min 2.07 _diffrn_standards_decay_% 2.89 _diffrn_standards_interval_count 97 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu 0.409 _exptl_absorpt_correction_T_max 0.921 _exptl_absorpt_correction_T_min 0.860 _exptl_absorpt_correction_type empirical _exptl_absorpt_process_details '(SHELXS97; Sheldrick, 1990)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.365 _exptl_crystal_density_method 'not measured' _exptl_crystal_description plate _exptl_crystal_F_000 268 _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.20 _refine_diff_density_max 0.215 _refine_diff_density_min -0.205 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.005 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 74 _refine_ls_number_reflns 1097 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.055 _refine_ls_R_factor_all 0.0585 _refine_ls_R_factor_gt 0.0387 _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^)+(0.0578P)^2^] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0967 _refine_ls_wR_factor_ref 0.1036 _reflns_number_gt 804 _reflns_number_total 1097 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file ob6214.cif _[local]_cod_data_source_block I _[local]_cod_cif_authors_sg_H-M 'P 21/c' _cod_depositor_comments ; The following automatic conversions were performed: '_chemical_melting_point' value '467-468.5' was changed to '467.8(8)' - the average value was taken and precision was estimated. Automatic conversion script Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana The following automatic conversions were performed: '_chemical_melting_point' value '467-468.5' was changed to '467.8(8)' - the average value was taken and precision was estimated. Automatic conversion script Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana ; _cod_original_cell_volume 619.0(2) _cod_database_code 2202112 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_disorder_assembly _atom_site_disorder_group _atom_site_type_symbol S 0.73870(16) 0.35819(4) 0.32720(10) 0.0483(3) Uani d . 1 . . S N1 1.0288(4) 0.35026(10) 0.7244(3) 0.0364(5) Uani d . 1 . . N N2 0.6764(4) 0.42550(10) 0.6515(3) 0.0351(5) Uani d . 1 . . N C1 0.8145(5) 0.37769(11) 0.5692(4) 0.0335(6) Uani d . 1 . . C C2 1.0220(7) 0.38040(13) 0.8990(4) 0.0477(7) Uani d . 1 . . C H2 1.1459 0.3701 1.0254 0.057 Uiso calc R 1 . . H C3 0.8064(6) 0.42695(14) 0.8548(4) 0.0466(7) Uani d . 1 . . C H3 0.7529 0.4553 0.9445 0.056 Uiso calc R 1 . . H C4 0.4371(5) 0.46939(11) 0.5390(4) 0.0400(6) Uani d . 1 . . C H4A 0.3183 0.4843 0.6235 0.048 Uiso calc R 1 . . H H4B 0.3071 0.4443 0.4285 0.048 Uiso calc R 1 . . H C5 1.2262(6) 0.29465(13) 0.7078(4) 0.0506(8) Uani d . 1 . . C H5A 1.1246 0.2523 0.7067 0.061 Uiso calc R 1 . . H H5B 1.4042 0.2958 0.8190 0.061 Uiso calc R 1 . . H H5C 1.2796 0.2993 0.5867 0.061 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 S 0.0456(4) 0.0641(5) 0.0335(4) -0.0011(4) 0.0089(3) -0.0072(3) N1 0.0343(11) 0.0357(11) 0.0377(12) 0.0028(9) 0.0081(9) 0.0053(9) N2 0.0364(11) 0.0330(11) 0.0343(12) 0.0016(9) 0.0081(9) 0.0009(9) C1 0.0313(13) 0.0323(13) 0.0366(14) -0.0043(10) 0.0096(11) 0.0043(10) C2 0.0504(17) 0.0559(17) 0.0304(14) 0.0039(14) 0.0018(12) 0.0038(12) C3 0.0541(17) 0.0499(16) 0.0347(15) 0.0032(14) 0.0111(13) -0.0073(12) C4 0.0283(13) 0.0378(14) 0.0528(16) 0.0026(11) 0.0103(12) 0.0043(12) C5 0.0438(17) 0.0422(16) 0.066(2) 0.0083(13) 0.0163(15) 0.0104(13) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag S C1 . 1.679(2) yes N1 C1 . 1.358(3) yes N1 C2 . 1.374(3) yes N1 C5 . 1.459(3) no N2 C1 . 1.364(3) yes N2 C3 . 1.381(3) yes N2 C4 . 1.451(3) yes C2 C3 . 1.329(4) yes C2 H2 . 0.9300 no C3 H3 . 0.9300 no C4 H4A . 0.9700 no C4 H4B . 0.9700 no C5 H5A . 0.9600 no C5 H5B . 0.9600 no C5 H5C . 0.9600 no 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' 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 C1 N1 C2 110.0(2) no C1 N1 C5 124.6(2) yes C2 N1 C5 125.3(2) no C1 N2 C3 109.6(2) no C1 N2 C4 124.4(2) yes C3 N2 C4 125.9(2) yes N1 C1 N2 105.2(2) no N1 C1 S 127.63(19) yes N2 C1 S 127.16(18) yes C3 C2 N1 107.7(2) no C3 C2 H2 126.1 no N1 C2 H2 126.1 no C2 C3 N2 107.5(2) no C2 C3 H3 126.3 no N2 C3 H3 126.3 no N2 C4 H4A 109.5 no N2 C4 H4B 109.5 no H4A C4 H4B 108.1 no N1 C5 H5A 109.5 no N1 C5 H5B 109.5 no H5A C5 H5B 109.5 no N1 C5 H5C 109.5 no H5A C5 H5C 109.5 no H5B C5 H5C 109.5 no 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_publ_flag C2 N1 C1 N2 0.2(3) no C5 N1 C1 N2 177.4(2) yes C2 N1 C1 S 179.3(2) yes C5 N1 C1 S -3.6(3) yes C3 N2 C1 N1 0.0(3) no C4 N2 C1 N1 177.93(19) yes C3 N2 C1 S -178.99(19) yes C4 N2 C1 S -1.1(3) yes C1 N1 C2 C3 -0.4(3) yes C5 N1 C2 C3 -177.6(2) no N1 C2 C3 N2 0.4(3) no C1 N2 C3 C2 -0.3(3) no C4 N2 C3 C2 -178.2(2) yes _cod_database_fobs_code 2202112 _journal_paper_doi 10.1107/S1600536803003623