#------------------------------------------------------------------------------ #$Date: 2025-08-18 23:52:38 +0100 (Mon, 18 Aug 2025) $ #$Revision: 301791 $ #$URL: svn://www.crystallography.net/cod/cif/2/00/81/2008159.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_2008159 loop_ _publ_author_name 'Beck, Johannes' 'Walter, J\"org' _publ_section_title ; Ethyl mustard oil sulfide hydrochloride ; _journal_issue 2 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first 260 _journal_page_last 262 _journal_paper_doi 10.1107/S0108270198011184 _journal_volume 55 _journal_year 1999 _chemical_formula_iupac 'C6 H11 N2 S3 1+, Cl 1-' _chemical_formula_moiety 'C6 H11 N2 S3, Cl' _chemical_formula_sum 'C6 H11 Cl N2 S3' _chemical_formula_weight 242.82 _chemical_name_common ; Ethyl mustard oil sulphide Hydrochloride ; _chemical_name_systematic ; 4-Ethyl-5-ethyliminium-1,2,4-dithiazolidine-3-thione chloride ; _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' _cell_angle_alpha 90.00 _cell_angle_beta 115.51(4) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 9.327(5) _cell_length_b 17.472(8) _cell_length_c 7.296(4) _cell_measurement_reflns_used 236 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 25.49 _cell_measurement_theta_min 4.82 _cell_volume 1073.1(10) _computing_cell_refinement IPDS _computing_data_collection 'IPDS (Stoe & Cie, 1995)' _computing_data_reduction IPDS _computing_publication_material SHELXL-93 _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _diffrn_ambient_temperature 293(2) _diffrn_detector_area_resol_mean 6.67 _diffrn_measured_fraction_theta_full 94.18 _diffrn_measured_fraction_theta_max 94.18 _diffrn_measurement_device_type 'Stoe Imaging Plate Diffraction System (IPDS)' _diffrn_measurement_method IPDS _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0432 _diffrn_reflns_av_sigmaI/netI 0.0266 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_number 6577 _diffrn_reflns_theta_full 26.05 _diffrn_reflns_theta_max 25.95 _diffrn_reflns_theta_min 4.64 _exptl_absorpt_coefficient_mu 0.890 _exptl_absorpt_correction_T_max 0.9310 _exptl_absorpt_correction_T_min 0.7145 _exptl_absorpt_correction_type gaussian _exptl_absorpt_process_details '(HABITUS; Herrendorf, 1993)' _exptl_crystal_colour 'translucent, pale yellow' _exptl_crystal_density_diffrn 1.503 _exptl_crystal_density_method 'not measured' _exptl_crystal_description 'rectangular plate' _exptl_crystal_F_000 504 _exptl_crystal_size_max 0.53 _exptl_crystal_size_mid 0.38 _exptl_crystal_size_min 0.08 _refine_diff_density_max .352 _refine_diff_density_min -.406 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_obs 1.068 _refine_ls_goodness_of_fit_ref 1.063 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 113 _refine_ls_number_reflns 1959 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.063 _refine_ls_restrained_S_obs 1.068 _refine_ls_R_factor_all 0.0426 _refine_ls_R_factor_gt 0.0370 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^)+( 0.0596P)^2^+0.6557P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_obs 0.1034 _refine_ls_wR_factor_ref 0.1101 _reflns_number_gt 1726 _reflns_number_total 1959 _reflns_threshold_expression I>2\s(I) _cod_data_source_file jz1288.cif _cod_data_source_block structural _cod_depositor_comments ; The following automatic conversions were performed: '_exptl_absorpt_correction_type' value 'Gaussian' changed to 'gaussian' 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 'P 21/c' _cod_database_code 2008159 _cod_database_fobs_code 2008159 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_group _atom_site_type_symbol Cl -0.02713(9) 0.06867(4) 0.23126(12) 0.0544(2) Uani d . 1 . Cl S1 -0.02080(7) 0.24018(3) 0.24501(9) 0.0368(2) Uani d . 1 . S S2 -0.24769(8) 0.20460(3) 0.18793(10) 0.0424(2) Uani d . 1 . S S3 -0.51668(10) 0.30366(5) 0.1052(2) 0.0658(3) Uani d . 1 . S N1 0.0370(3) 0.38909(13) 0.2610(3) 0.0400(5) Uani d . 1 . N H1 0.017(4) 0.4344(19) 0.259(4) 0.049(9) Uiso d . 1 . H C1 -0.0680(3) 0.33722(13) 0.2386(3) 0.0319(5) Uani d . 1 . C C11 0.1990(3) 0.3723(2) 0.2885(5) 0.0486(7) Uani d . 1 . C H11A 0.2120(3) 0.3904(2) 0.1708(5) 0.058 Uiso calc R 1 . H H11B 0.2152(3) 0.3174(2) 0.2975(5) 0.058 Uiso calc R 1 . H C12 0.3206(4) 0.4087(3) 0.4733(7) 0.0892(14) Uani d . 1 . C H12A 0.4245(4) 0.3963(3) 0.4854(7) 0.134 Uiso calc R 1 . H H12B 0.3096(4) 0.3903(3) 0.5905(7) 0.134 Uiso calc R 1 . H H12C 0.3064(4) 0.4633(3) 0.4639(7) 0.134 Uiso calc R 1 . H N2 -0.2203(2) 0.35455(11) 0.2041(3) 0.0353(4) Uani d . 1 . N C2 -0.3280(3) 0.29555(14) 0.1664(4) 0.0389(6) Uani d . 1 . C C21 -0.2742(3) 0.43525(13) 0.1902(4) 0.0409(6) Uani d . 1 . C H21A -0.1884(3) 0.46635(13) 0.2856(4) 0.049 Uiso calc R 1 . H H21B -0.3625(3) 0.43810(13) 0.2269(4) 0.049 Uiso calc R 1 . H C22 -0.3253(3) 0.4664(2) -0.0211(5) 0.0521(7) Uani d . 1 . C H22A -0.3595(3) 0.5185(2) -0.0259(5) 0.078 Uiso calc R 1 . H H22B -0.4114(3) 0.4361(2) -0.1154(5) 0.078 Uiso calc R 1 . H H22C -0.2376(3) 0.4644(2) -0.0567(5) 0.078 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 Cl 0.0636(5) 0.0275(4) 0.0688(5) 0.0050(3) 0.0253(4) 0.0004(3) S1 0.0458(4) 0.0252(3) 0.0421(4) 0.0043(2) 0.0216(3) 0.0025(2) S2 0.0488(4) 0.0288(3) 0.0502(4) -0.0041(2) 0.0218(3) -0.0003(2) S3 0.0504(5) 0.0583(5) 0.0925(7) -0.0052(4) 0.0344(4) -0.0069(4) N1 0.0394(11) 0.0272(11) 0.0530(14) 0.0029(9) 0.0196(10) 0.0009(9) C1 0.0390(12) 0.0284(11) 0.0266(12) 0.0032(9) 0.0124(9) 0.0017(8) C11 0.0388(13) 0.0381(14) 0.068(2) -0.0003(11) 0.0226(13) -0.0022(13) C12 0.048(2) 0.103(3) 0.093(3) 0.011(2) 0.008(2) -0.033(2) N2 0.0387(10) 0.0286(10) 0.0405(12) 0.0029(8) 0.0189(9) -0.0005(8) C2 0.0434(13) 0.0343(13) 0.0401(14) -0.0031(10) 0.0190(11) -0.0024(10) C21 0.0415(13) 0.0252(12) 0.058(2) 0.0047(9) 0.0227(11) -0.0032(10) C22 0.051(2) 0.0403(15) 0.061(2) 0.0106(12) 0.0206(13) 0.0119(13) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source Cl Cl .1480 .1590 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S .1250 .1230 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N .0060 .0030 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' C C .0030 .0020 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H .0000 .0000 '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 S1 S2 93.55(9) yes C2 S2 S1 96.17(9) yes C1 N1 C11 123.9(2) no C1 N1 H1 122.(2) no C11 N1 H1 114.(2) no N1 C1 N2 122.6(2) no N1 C1 S1 120.6(2) no N2 C1 S1 116.8(2) yes N1 C11 C12 112.3(3) no N1 C11 H11A 109.2(2) no C12 C11 H11A 109.2(2) no N1 C11 H11B 109.15(14) no C12 C11 H11B 109.2(2) no H11A C11 H11B 107.9 no C11 C12 H12A 109.5(2) no C11 C12 H12B 109.5(2) no H12A C12 H12B 109.5 no C11 C12 H12C 109.5(2) no H12A C12 H12C 109.5 no H12B C12 H12C 109.5 no C1 N2 C2 118.7(2) yes C1 N2 C21 121.2(2) no C2 N2 C21 119.9(2) no N2 C2 S3 126.7(2) no N2 C2 S2 114.6(2) yes S3 C2 S2 118.63(15) no N2 C21 C22 111.2(2) no N2 C21 H21A 109.40(13) no C22 C21 H21A 109.4(2) no N2 C21 H21B 109.40(12) no C22 C21 H21B 109.4(2) no H21A C21 H21B 108.0 no C21 C22 H22A 109.47(15) no C21 C22 H22B 109.5(2) no H22A C22 H22B 109.5 no C21 C22 H22C 109.5(2) no H22A C22 H22C 109.5 no H22B C22 H22C 109.5 no 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 S1 C1 . 1.747(2) yes S1 S2 . 2.0685(14) yes S2 C2 . 1.735(3) yes S3 C2 . 1.624(3) yes N1 C1 . 1.292(3) yes N1 H1 . 0.81(3) yes N1 C11 . 1.466(3) yes C11 C12 . 1.480(5) yes C1 N2 . 1.366(3) yes C11 H11A . 0.97 no C11 H11B . 0.97 no C12 H12A . 0.96 no C12 H12B . 0.96 no C12 H12C . 0.96 no N2 C2 . 1.382(3) yes N2 C21 . 1.486(3) yes C21 C22 . 1.505(4) yes C21 H21A . 0.97 no C21 H21B . 0.97 no C22 H22A . 0.96 no C22 H22B . 0.96 no C22 H22C . 0.96 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 N1 H1 Cl 2_555 0.81(3) 2.35(3) 3.140(3) 166(3) yes loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 PubChem 139056424