#------------------------------------------------------------------------------ #$Date: 2014-04-20 07:52:50 +0300 (Sun, 20 Apr 2014) $ #$Revision: 110989 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/21/48/7214896.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/ # # All data on this site have been placed in the public domain by the # contributors. # data_7214896 loop_ _publ_author_name 'Yufit, Dmitry S.' 'Zubatyuk, Roman' 'Shishkin, Oleg V.' 'Howard, Judith A. K.' _publ_section_title ; Low-melting molecular complexes. Halogen bonds in molecular complexes of bromoform ; _journal_issue 23 _journal_name_full CrystEngComm _journal_page_first 8222 _journal_paper_doi 10.1039/c2ce26191j _journal_volume 14 _journal_year 2012 _chemical_absolute_configuration ad _chemical_formula_moiety 'C2 H6 O S, C H Br3' _chemical_formula_sum 'C3 H7 Br3 O S' _chemical_formula_weight 330.88 _chemical_melting_point 237.0(10) _chemical_name_systematic ; molecular complex of bromoform with dimethylsulfoxide (1:1) ; _space_group_crystal_system monoclinic _space_group_IT_number 9 _space_group_name_Hall 'C -2yc' _space_group_name_H-M_alt 'C 1 c 1' _symmetry_space_group_name_Hall 'C -2yc' _symmetry_space_group_name_H-M 'C 1 c 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary iterative _atom_sites_solution_secondary difmap _audit_creation_date 2012-07-16 _audit_creation_method ; Olex2 1.2-beta (compiled 2012.05.09 svn.r2324, GUI svn.r4230) ; _cell_angle_alpha 90.00 _cell_angle_beta 94.923(11) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 7.9562(8) _cell_length_b 9.6768(9) _cell_length_c 12.0633(17) _cell_measurement_reflns_used 2036 _cell_measurement_temperature 225 _cell_measurement_theta_max 33.0749 _cell_measurement_theta_min 3.3155 _cell_volume 925.33(18) _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET) (compiled Aug 3 2011,13:03:54) ; _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET) (compiled Aug 3 2011,13:03:54) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET) (compiled Aug 3 2011,13:03:54) ; _computing_molecular_graphics ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_publication_material ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_structure_refinement ; XL, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 ; _computing_structure_solution ; olex2.solve (L.J. Bourhis, O.V. Dolomanov, R.J. Gildea, J.A.K. Howard, H. Puschmann, in preparation, 2011) ; _diffrn_ambient_temperature 225 _diffrn_detector CCD _diffrn_detector_area_resol_mean 16.1511 _diffrn_detector_type Sapphire3 _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 1.000 _diffrn_measurement_details ; 1 omega -63.00 32.00 0.5000 15.0000 omega____ theta____ kappa____ phi______ frames - -31.1216 77.0000 120.0000 190 2 omega -101.00 35.00 0.5000 15.0000 omega____ theta____ kappa____ phi______ frames - -31.1216 -19.0000 -30.0000 272 3 omega 71.00 103.00 0.5000 15.0000 omega____ theta____ kappa____ phi______ frames - 31.7466 179.0000 120.0000 64 4 omega -102.00 -7.00 0.5000 15.0000 omega____ theta____ kappa____ phi______ frames - -31.1216 -57.0000 -90.0000 190 5 omega -105.00 0.00 0.5000 15.0000 omega____ theta____ kappa____ phi______ frames - -31.1216 -38.0000 150.0000 210 6 omega -55.00 39.00 0.5000 15.0000 omega____ theta____ kappa____ phi______ frames - -31.1216 57.0000 0.0000 188 7 omega 56.00 112.00 0.5000 15.0000 omega____ theta____ kappa____ phi______ frames - 31.7466 179.0000 -60.0000 112 8 omega -1.00 104.00 0.5000 15.0000 omega____ theta____ kappa____ phi______ frames - 31.7466 77.0000 90.0000 210 9 omega 56.00 112.00 0.5000 15.0000 omega____ theta____ kappa____ phi______ frames - 31.7466 179.0000 0.0000 112 10 omega -111.00 -81.00 0.5000 15.0000 omega____ theta____ kappa____ phi______ frames - -31.1216 -179.0000 -30.0000 60 ; _diffrn_measurement_device '3-circle diffractometer' _diffrn_measurement_device_type 'Xcalibur, Sapphire3, Gemini ultra' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_UB_11 0.0824365000 _diffrn_orient_matrix_UB_12 0.0219456000 _diffrn_orient_matrix_UB_13 0.0195218000 _diffrn_orient_matrix_UB_21 -0.0312668000 _diffrn_orient_matrix_UB_22 0.0672882000 _diffrn_orient_matrix_UB_23 0.0089208000 _diffrn_orient_matrix_UB_31 -0.0160243000 _diffrn_orient_matrix_UB_32 -0.0186913000 _diffrn_orient_matrix_UB_33 0.0549584000 _diffrn_radiation_collimation monochromator _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.7107 _diffrn_radiation_xray_symbol Mo _diffrn_reflns_av_R_equivalents 0.1023 _diffrn_reflns_av_unetI/netI 0.0979 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_number 7041 _diffrn_reflns_theta_full 29.47 _diffrn_reflns_theta_max 29.47 _diffrn_reflns_theta_min 3.32 _diffrn_source 'Enhance (Mo) X-ray Source' _diffrn_source_current n/a _diffrn_source_type 'sealed tube' _diffrn_source_voltage n/a _exptl_absorpt_coefficient_mu 13.229 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.14125 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET) (compiled Aug 3 2011,13:03:54) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour 'dull light white' _exptl_crystal_colour_lustre dull _exptl_crystal_colour_modifier light _exptl_crystal_colour_primary white _exptl_crystal_density_diffrn 2.375 _exptl_crystal_density_method 'not measured' _exptl_crystal_description cylinder _exptl_crystal_F_000 616 _exptl_crystal_recrystallization_method 'Grown in situ @228K' _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.15 _refine_diff_density_max 1.841 _refine_diff_density_min -2.000 _refine_diff_density_rms 0.267 _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.06(4) _refine_ls_extinction_coef 0.0049(11) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method SHELXL _refine_ls_goodness_of_fit_ref 1.036 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 76 _refine_ls_number_reflns 2557 _refine_ls_number_restraints 2 _refine_ls_restrained_S_all 1.035 _refine_ls_R_factor_all 0.1038 _refine_ls_R_factor_gt 0.0833 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1357P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.2103 _refine_ls_wR_factor_ref 0.2358 _reflns_number_gt 1915 _reflns_number_total 2557 _reflns_threshold_expression >2sigma(I) _[local]_cod_data_source_file c2ce26191j.txt _[local]_cod_data_source_block II_bbs _cod_depositor_comments ; The following automatic conversions were performed: '_chemical_melting_point' value '236-238' was changed to '237.0(10)' - the average value was taken and precision was estimated. Automatic conversion script Id: cif_fix_values 2281 2013-09-26 08:29:07Z andrius ; _cod_database_code 7214896 _chemical_oxdiff_formula 'C3 H7 Br3 S1 O1' _chemical_oxdiff_usercomment 'Grown in situ at 228K' _reflns_odcompleteness_completeness 99.88 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 31.44 loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 'x, -y, z+1/2' 3 'x+1/2, y+1/2, z' 4 'x+1/2, -y+1/2, z+1/2' loop_ _atom_site_label _atom_site_type_symbol _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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags S1 S 0.8588(4) 0.5192(4) 0.8467(3) 0.0411(8) Uani 1 1 d . O1 O 0.6850(12) 0.5758(13) 0.8576(9) 0.052(3) Uani 1 1 d . C1 C 0.872(2) 0.3574(16) 0.9153(15) 0.048(4) Uani 1 1 d . H1A H 0.7907 0.2951 0.8794 0.073 Uiso 1 1 calc R H1B H 0.8496 0.3693 0.9916 0.073 Uiso 1 1 calc R H1C H 0.9833 0.3199 0.9120 0.073 Uiso 1 1 calc R C2 C 0.997(2) 0.6099(16) 0.9443(19) 0.065(5) Uani 1 1 d . H2A H 0.9599 0.5989 1.0175 0.097 Uiso 1 1 calc R H2B H 0.9969 0.7062 0.9253 0.097 Uiso 1 1 calc R H2C H 1.1092 0.5737 0.9431 0.097 Uiso 1 1 calc R Br1 Br 0.50479(14) 0.48018(14) 0.55461(12) 0.0433(4) Uani 1 1 d . Br2 Br 0.27358(18) 0.35768(18) 0.73364(15) 0.0547(5) Uani 1 1 d . Br3 Br 0.22470(18) 0.66779(16) 0.65021(14) 0.0512(5) Uani 1 1 d . C1S C 0.3863(17) 0.5177(12) 0.6825(12) 0.040(3) Uani 1 1 d . H1S H 0.4687 0.5484 0.7425 0.048 Uiso 1 1 calc R loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S1 0.0255(15) 0.049(2) 0.0474(18) 0.0060(14) -0.0060(12) -0.0027(13) O1 0.024(4) 0.070(7) 0.059(6) 0.013(5) -0.009(4) 0.000(5) C1 0.040(8) 0.035(7) 0.070(10) -0.006(6) 0.004(7) -0.004(6) C2 0.027(7) 0.035(7) 0.127(16) -0.003(9) -0.025(8) 0.000(6) Br1 0.0320(6) 0.0366(7) 0.0604(9) 0.0017(5) -0.0020(5) 0.0061(5) Br2 0.0404(8) 0.0488(9) 0.0744(11) 0.0148(7) 0.0012(7) 0.0034(6) Br3 0.0416(8) 0.0425(7) 0.0668(9) -0.0041(6) -0.0102(6) 0.0182(6) C1S 0.032(6) 0.025(6) 0.060(8) -0.007(5) -0.009(6) 0.013(5) 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' Br Br -0.2901 2.4595 '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 O1 S1 C1 107.5(7) O1 S1 C2 106.5(8) C2 S1 C1 96.8(8) S1 C1 H1A 109.5 S1 C1 H1B 109.5 S1 C1 H1C 109.5 H1A C1 H1B 109.5 H1A C1 H1C 109.5 H1B C1 H1C 109.5 S1 C2 H2A 109.5 S1 C2 H2B 109.5 S1 C2 H2C 109.5 H2A C2 H2B 109.5 H2A C2 H2C 109.5 H2B C2 H2C 109.5 Br1 C1S Br2 112.5(6) Br1 C1S Br3 110.0(7) Br1 C1S H1S 108.0 Br2 C1S Br3 110.2(7) Br2 C1S H1S 108.0 Br3 C1S H1S 108.0 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance S1 O1 1.504(11) S1 C1 1.770(16) S1 C2 1.774(17) C1 H1A 0.9600 C1 H1B 0.9600 C1 H1C 0.9600 C2 H2A 0.9600 C2 H2B 0.9600 C2 H2C 0.9600 Br1 C1S 1.910(14) Br2 C1S 1.918(14) Br3 C1S 1.957(12) C1S H1S 0.9800