#------------------------------------------------------------------------------ #$Date: 2013-12-28 13:58:47 +0000 (Sat, 28 Dec 2013) $ #$Revision: 91933 $ #$URL: svn://www.crystallography.net/cod/cif/2/01/01/2010197.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_2010197 loop_ _publ_author_name 'Howard, Judith A.K.' 'Batsanov, Andrei S.' 'O'Hagan, David' 'White, Jeffrey' _publ_section_title ; 3-Chloro- and 3-bromo-2-oxopropyl-p-toluenesulfonate ; _journal_issue 11 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first 1825 _journal_page_last 1828 _journal_volume 50 _journal_year 1994 _chemical_formula_analytical 'C39.3%, H3.6%' _chemical_formula_sum 'C10 H11 Br O4 S' _chemical_formula_weight 307.16 _chemical_melting_point 67.0 _chemical_name_common 3-Bromo-2-oxopropyltosylate _chemical_name_systematic ' 3-Bromo-2-oxopropyl-p-toluenesulfonate' _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' _audit_creation_method SHELXL _cell_angle_alpha 90.00 _cell_angle_beta 110.48(3) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 11.002(2) _cell_length_b 5.160(2) _cell_length_c 22.490(3) _cell_measurement_reflns_used 24 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 14.5 _cell_measurement_theta_min 13.5 _cell_volume 1196.1(6) _computing_cell_refinement 'MSC/AFC Diffractometer Control Software' _computing_data_collection ;MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1988) ; _computing_data_reduction 'TEXSAN (Molecular Structure Corporation, 1989)' _computing_molecular_graphics 'SHELXTL-Plus (Sheldrick, 1991)' _computing_publication_material SHELXL93 _computing_structure_refinement 'SHELXL93 (Sheldrick, 1994)' _computing_structure_solution 'SHELXS86 (Sheldrick, 1990)' _diffrn_ambient_temperature 293(2) _diffrn_measurement_device 'Rigaku AFC6S four-circle diffractometer' _diffrn_measurement_method 2\q/\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 0.0288 _diffrn_reflns_av_sigmaI/netI 0.0867 _diffrn_reflns_limit_h_max 0 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_k_max 0 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_number 2893 _diffrn_reflns_theta_max 27.50 _diffrn_reflns_theta_min 3.21 _diffrn_standards_decay_% 0.2 _diffrn_standards_interval_count 150 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu 3.606 _exptl_absorpt_correction_T_max 0.7165 _exptl_absorpt_correction_T_min 0.4143 _exptl_absorpt_correction_type 'Analytical, 6 faces indexed' _exptl_crystal_colour Colourless _exptl_crystal_density_diffrn 1.706 _exptl_crystal_description Plate _exptl_crystal_F_000 616 _exptl_crystal_size_max 0.51 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.10 _refine_diff_density_max 0.344 _refine_diff_density_min -0.340 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_all 1.018 _refine_ls_goodness_of_fit_obs 1.117 _refine_ls_hydrogen_treatment 'H atoms: geom, riding, rigid-body' _refine_ls_matrix_type full _refine_ls_number_parameters 149 _refine_ls_number_reflns 2751 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.022 _refine_ls_restrained_S_obs 1.117 _refine_ls_R_factor_all 0.1236 _refine_ls_R_factor_obs 0.0401 _refine_ls_shift/esd_max -0.009 _refine_ls_shift/esd_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_scheme ;calc w = 1/[\s^2^(F~o~^2^)+(0.0362P)^2^+1.0468P] where P = (F~o~^2^+2F~c~^2^)/3 ; _refine_ls_wR_factor_all 0.1092 _refine_ls_wR_factor_obs 0.0877 _reflns_number_observed 1550 _reflns_number_total 2752 _reflns_observed_criterion >2\s(I) _[local]_cod_data_source_file hu1109.cif _[local]_cod_data_source_block 2 _[local]_cod_cif_authors_sg_H-M 'P 21/c' _[local]_cod_chemical_formula_sum_orig 'C10 H11 Br1 O4 S1' _cod_depositor_comments ; The following automatic conversions were performed: '_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic' 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 'Monoclinic' changed to 'monoclinic' 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 1196.3(3) _cod_database_code 2010197 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_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 Br 0.0868(4) 0.0567(3) 0.0447(3) 0.0080(3) 0.0263(3) -0.0059(3) S 0.0355(5) 0.0305(5) 0.0339(5) 0.0014(5) 0.0144(4) -0.0001(4) O1 0.0387(15) 0.038(2) 0.0302(13) -0.0065(13) 0.0141(12) -0.0050(13) O2 0.049(2) 0.033(2) 0.048(2) -0.0068(14) 0.0205(14) 0.0020(14) O3 0.042(2) 0.042(2) 0.043(2) 0.0100(14) 0.0170(13) 0.0009(14) O4 0.059(2) 0.055(2) 0.054(2) -0.018(2) 0.021(2) -0.012(2) C1 0.032(2) 0.033(2) 0.027(2) -0.001(2) 0.011(2) -0.003(2) C2 0.034(2) 0.041(2) 0.037(2) 0.001(2) 0.016(2) 0.002(2) C3 0.032(2) 0.049(3) 0.043(2) 0.007(2) 0.011(2) 0.001(2) C4 0.051(3) 0.039(2) 0.032(2) 0.004(2) 0.010(2) 0.002(2) C5 0.054(3) 0.065(3) 0.040(2) -0.001(3) 0.022(2) 0.011(2) C6 0.037(2) 0.061(3) 0.042(2) 0.004(2) 0.019(2) 0.006(2) C7 0.073(3) 0.063(4) 0.051(3) 0.016(3) 0.017(3) 0.017(3) C8 0.037(2) 0.040(3) 0.043(2) -0.002(2) 0.013(2) -0.008(2) C9 0.041(2) 0.036(2) 0.031(2) 0.000(2) 0.009(2) 0.003(2) C10 0.056(3) 0.036(3) 0.040(2) -0.002(2) 0.018(2) -0.004(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_thermal_displace_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_occupancy _atom_site_disorder_group _atom_site_type_symbol Br 0.16417(5) 0.19840(11) 0.01966(2) 0.0619(2) Uani d . 1 . Br S 0.21392(9) 0.9838(2) 0.23277(5) 0.0327(2) Uani d . 1 . S O1 0.1776(2) 0.8066(5) 0.17120(11) 0.0351(6) Uani d . 1 . O O2 0.2994(3) 1.1711(5) 0.22244(13) 0.0425(7) Uani d . 1 . O O3 0.0971(3) 1.0660(6) 0.24121(13) 0.0418(7) Uani d . 1 . O O4 -0.0184(3) 0.2805(6) 0.09153(15) 0.0559(9) Uani d . 1 . O C1 0.2986(3) 0.7725(7) 0.2942(2) 0.0306(9) Uani d . 1 . C C2 0.4257(4) 0.7088(8) 0.3032(2) 0.0364(9) Uani d . 1 . C H2 0.4675(4) 0.7827(8) 0.2779(2) 0.044 Uiso calc R 1 . H C3 0.4901(4) 0.5343(9) 0.3502(2) 0.0420(10) Uani d . 1 . C H3 0.5754(4) 0.4893(9) 0.3561(2) 0.050 Uiso calc R 1 . H C4 0.4289(4) 0.4246(9) 0.3889(2) 0.0418(10) Uani d . 1 . C C5 0.3028(4) 0.4939(10) 0.3798(2) 0.0512(12) Uani d . 1 . C H5 0.2618(4) 0.4235(10) 0.4058(2) 0.061 Uiso calc R 1 . H C6 0.2356(4) 0.6669(9) 0.3323(2) 0.0450(11) Uani d . 1 . C H6 0.1502(4) 0.7111(9) 0.3262(2) 0.054 Uiso calc R 1 . H C7 0.4994(5) 0.2299(10) 0.4393(2) 0.0639(14) Uani d . 1 . C H7A 0.5883(10) 0.282(4) 0.4590(11) 0.102(12) Uiso calc R 1 . H H7B 0.496(3) 0.0624(16) 0.4202(4) 0.102(12) Uiso calc R 1 . H H7C 0.459(2) 0.222(5) 0.4708(9) 0.102(12) Uiso calc R 1 . H C8 0.0665(4) 0.6369(8) 0.1575(2) 0.0404(10) Uani d . 1 . C H8A -0.0126(4) 0.7385(8) 0.1427(2) 0.067(11) Uiso calc R 1 . H H8B 0.0695(4) 0.5470(8) 0.1959(2) 0.067(11) Uiso calc R 1 . H C9 0.0660(4) 0.4416(8) 0.1073(2) 0.0370(10) Uani d . 1 . C C10 0.1735(4) 0.4637(8) 0.0809(2) 0.0435(11) Uani d . 1 . C H10A 0.2563(4) 0.4518(8) 0.1154(2) 0.049(9) Uiso calc R 1 . H H10B 0.1690(4) 0.6322(8) 0.0611(2) 0.049(9) Uiso calc R 1 . H 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 Br C10 . 1.920(4) yes S O2 . 1.424(3) yes S O3 . 1.428(3) yes S O1 . 1.590(3) yes S C1 . 1.750(4) yes O1 C8 . 1.447(5) yes O4 C9 . 1.204(5) yes C1 C2 . 1.381(5) ? C1 C6 . 1.389(5) ? C2 C3 . 1.381(6) ? C3 C4 . 1.394(6) ? C4 C5 . 1.377(6) ? C4 C7 . 1.510(6) ? C5 C6 . 1.389(6) ? C8 C9 . 1.512(5) yes C9 C10 . 1.501(5) yes 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 _geom_angle_publ_flag O2 S O3 119.8(2) yes O2 S O1 103.1(2) yes O3 S O1 108.9(2) yes O2 S C1 110.6(2) ? O3 S C1 109.6(2) ? O1 S C1 103.4(2) yes C8 O1 S 118.0(2) yes C2 C1 C6 120.9(4) yes C2 C1 S 119.8(3) ? C6 C1 S 119.3(3) ? C3 C2 C1 119.4(4) ? C2 C3 C4 120.8(4) ? C5 C4 C3 118.9(4) ? C5 C4 C7 120.7(4) ? C3 C4 C7 120.4(4) ? C4 C5 C6 121.3(4) ? C1 C6 C5 118.7(4) ? O1 C8 C9 110.2(3) yes O4 C9 C10 124.7(4) yes O4 C9 C8 118.7(4) yes C10 C9 C8 116.5(4) yes C9 C10 Br 112.2(3) yes 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 C1 S O1 76.9(3) yes C1 S O1 C8 80.6(3) yes S O1 C8 C9 -166.7(3) yes O1 C8 C9 C10 -1.6(5) yes C8 C9 C10 Br 178.2(3) yes _journal_paper_doi 10.1107/S0108270194006499