#------------------------------------------------------------------------------ #$Date: 2025-08-19 11:43:10 +0100 (Tue, 19 Aug 2025) $ #$Revision: 301803 $ #$URL: svn://www.crystallography.net/cod/cif/2/20/32/2203255.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_2203255 loop_ _publ_author_name 'Zawadski, Alexander' 'Parsons, Simon' _publ_section_title ; 2-Chloroethyl ethyl sulfide: a mustard gas analogue ; _journal_issue 2 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o225 _journal_page_last o227 _journal_paper_doi 10.1107/S1600536804000753 _journal_volume 60 _journal_year 2004 _chemical_formula_iupac 'C4 H9 Cl1 S1' _chemical_formula_moiety 'C4 H9 Cl1 S1' _chemical_formula_sum 'C4 H9 Cl S' _chemical_formula_weight 124.63 _chemical_name_systematic ; 2-Chloroethyl ethyl sulfide ; _space_group_IT_number 33 _symmetry_cell_setting orthorhombic _symmetry_space_group_name_Hall 'P 2c -2n' _symmetry_space_group_name_H-M 'P n a 21' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method CRYSTALS_ver_12-03-99 _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 15.343(3) _cell_length_b 8.5760(14) _cell_length_c 4.8863(8) _cell_measurement_reflns_used 3540 _cell_measurement_temperature 150 _cell_measurement_theta_max 29 _cell_measurement_theta_min 3 _cell_volume 642.95(19) _computing_cell_refinement SAINT _computing_data_collection 'SMART (Bruker, 2001)' _computing_data_reduction 'SAINT (Bruker, 2002)' _computing_molecular_graphics 'XP (Sheldrick, 1997)' _computing_publication_material ;CRYSTALS, EnCIFer (CCDC, 2002), PLATON (Spek, 2003) and WINGX (Farrugia, 1999) ; _computing_structure_refinement 'CRYSTALS (Watkin et al., 2003)' _computing_structure_solution 'SIR92 (Altomare et al., 1993)' _diffrn_ambient_temperature 150 _diffrn_measured_fraction_theta_full 0.997 _diffrn_measured_fraction_theta_max 0.941 _diffrn_measurement_device_type 'Bruker SMART APEX' _diffrn_measurement_method \w _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.03 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_l_max 6 _diffrn_reflns_limit_l_min -6 _diffrn_reflns_number 4048 _diffrn_reflns_theta_full 25.72 _diffrn_reflns_theta_max 28.26 _diffrn_reflns_theta_min 2.65 _diffrn_standards_decay_% 0.00 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.78 _exptl_absorpt_correction_T_max 0.790 _exptl_absorpt_correction_T_min 0.352 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS (Sheldrick, 2002)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.287 _exptl_crystal_density_meas ? _exptl_crystal_density_method . _exptl_crystal_description cylinder _exptl_crystal_F_000 264 _exptl_crystal_size_max 1.00 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.30 _refine_diff_density_max 0.36 _refine_diff_density_min -0.25 _refine_ls_abs_structure_details 'Flack (1983); 597 Friedel pairs' _refine_ls_abs_structure_Flack 0.23(12) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.01 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 56 _refine_ls_number_reflns 1438 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.028 _refine_ls_R_factor_gt 0.024 _refine_ls_shift/su_max 0.001 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details ; w = 1/[\s^2^(Fo^2^)+(0.0194P)^2^ + 0.136P] where P = (Fo^2^+2Fc^2^)/3 (SHELXL97; Sheldrick, 1997) ; _refine_ls_weighting_scheme calc _refine_ls_wR_factor_all 0.064 _refine_ls_wR_factor_gt 0.062 _refine_ls_wR_factor_ref 0.064 _reflns_number_gt 1313 _reflns_number_total 1441 _reflns_threshold_expression I>2\s(I) _cod_data_source_file ya6195.cif _cod_data_source_block I _cod_depositor_comments ; The following automatic conversions were performed: '_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic' 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 'Orthorhombic' changed to 'orthorhombic' 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_cell_volume 642.96(18) _cod_original_sg_symbol_H-M 'P n a 21 ' _cod_original_formula_sum 'C4 H9 Cl1 S1' _cod_database_code 2203255 loop_ _symmetry_equiv_pos_as_xyz x,y,z -x+1/2,y+1/2,z+1/2 x+1/2,-y+1/2,z -x,-y,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_occupancy _atom_site_type_symbol Cl1 0.44869(3) 0.12110(5) 0.13095(14) 0.0353 Uani 1.0000 Cl C2 0.37514(12) 0.1959(2) 0.3892(4) 0.0315 Uani 1.0000 C C3 0.32202(11) 0.0630(2) 0.5064(4) 0.0276 Uani 1.0000 C S4 0.24368(3) 0.13448(5) 0.75570(15) 0.0359 Uani 1.0000 S C5 0.15538(12) 0.1954(2) 0.5312(4) 0.0379 Uani 1.0000 C C6 0.10405(12) 0.0620(3) 0.4094(5) 0.0441 Uani 1.0000 C H21 0.4096 0.2463 0.5388 0.0377 Uiso 1.0000 H H22 0.3352 0.2745 0.3049 0.0377 Uiso 1.0000 H H31 0.3621 -0.0130 0.5975 0.0331 Uiso 1.0000 H H32 0.2901 0.0096 0.3545 0.0331 Uiso 1.0000 H H51 0.1145 0.2622 0.6391 0.0455 Uiso 1.0000 H H52 0.1809 0.2579 0.3780 0.0455 Uiso 1.0000 H H61 0.0569 0.1043 0.2890 0.0529 Uiso 1.0000 H H62 0.0774 -0.0012 0.5598 0.0529 Uiso 1.0000 H H63 0.1438 -0.0055 0.2987 0.0529 Uiso 1.0000 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 Cl1 0.0313(2) 0.0445(2) 0.0302(2) 0.00303(18) 0.0016(2) -0.0013(2) C2 0.0350(9) 0.0308(9) 0.0286(9) 0.0011(7) 0.0035(8) -0.0035(8) C3 0.0295(8) 0.0270(8) 0.0263(8) 0.0039(6) -0.0012(8) -0.0022(7) S4 0.0336(2) 0.0474(3) 0.0268(2) 0.0031(2) 0.0006(2) -0.0039(3) C5 0.0326(9) 0.0307(9) 0.0505(12) 0.0075(8) -0.0020(9) -0.0017(8) C6 0.0307(10) 0.0419(11) 0.0598(15) 0.0010(8) -0.0077(11) -0.0026(10) loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C ' 0.0033 0.0016 International_Tables_Vol_IV_Table_2.2B 'H ' 0.0000 0.0000 International_Tables_Vol_IV_Table_2.2B 'S ' 0.1246 0.1234 International_Tables_Vol_IV_Table_2.2B 'Cl ' 0.1484 0.1585 International_Tables_Vol_IV_Table_2.2B 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 H22 C2 H21 109.467 no H22 C2 C3 109.481 no H21 C2 C3 109.481 no H22 C2 Cl1 109.482 no H21 C2 Cl1 109.482 no C3 C2 Cl1 109.43(12) yes H32 C3 H31 109.467 no H32 C3 S4 109.131 no H31 C3 S4 109.131 no H32 C3 C2 109.131 no H31 C3 C2 109.131 no S4 C3 C2 110.83(12) yes C5 S4 C3 100.67(10) yes H52 C5 H51 109.466 no H52 C5 C6 108.313 no H51 C5 C6 108.313 no H52 C5 S4 108.313 no H51 C5 S4 108.314 no C6 C5 S4 114.06(14) yes H63 C6 H62 109.476 no H63 C6 H61 109.475 no H62 C6 H61 109.476 no H63 C6 C5 109.466 no H62 C6 C5 109.467 no H61 C6 C5 109.467 no loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag Cl1 C2 1.810(2) yes C2 H22 1.000 no C2 H21 1.000 no C2 C3 1.513(3) yes C3 H32 1.000 no C3 H31 1.000 no C3 S4 1.818(2) yes S4 C5 1.820(2) yes C5 H52 1.000 no C5 H51 1.000 no C5 C6 1.512(3) yes C6 H63 1.000 no C6 H62 1.000 no C6 H61 1.000 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 C5 S4 C3 C2 83.17(14) yes C3 S4 C5 C6 73.81(16) yes Cl1 C2 C3 S4 -177.38(9) yes loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 ChemSpider 12210 2 PubChem 12733