#------------------------------------------------------------------------------ #$Date: 2025-08-19 07:12:48 +0100 (Tue, 19 Aug 2025) $ #$Revision: 301798 $ #$URL: svn://www.crystallography.net/cod/cif/2/01/01/2010196.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_2010196 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_paper_doi 10.1107/S0108270194006499 _journal_volume 50 _journal_year 1994 _chemical_formula_analytical 'C45.5%, H4.1%' _chemical_formula_sum 'C10 H11 Cl O4 S' _chemical_formula_weight 262.70 _chemical_melting_point 75.4 _chemical_name_common 3-chloro-2-oxopropyltosylate _chemical_name_systematic ' 3-Chloro-2-oxopropyl-p-toluenesulfonate' _space_group_IT_number 4 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall 'P 2yb' _symmetry_space_group_name_H-M 'P 1 21 1' _audit_creation_method SHELXL _cell_angle_alpha 90.00 _cell_angle_beta 111.16(5) _cell_angle_gamma 90.00 _cell_formula_units_Z 2 _cell_length_a 10.888(8) _cell_length_b 5.095(3) _cell_length_c 10.923(8) _cell_measurement_reflns_used 22 _cell_measurement_temperature 150(2) _cell_measurement_theta_max 14 _cell_measurement_theta_min 13 _cell_volume 565.1(7) _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 150(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 0.0341 _diffrn_reflns_av_sigmaI/netI 0.0352 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_number 1182 _diffrn_reflns_theta_max 27.31 _diffrn_reflns_theta_min 3.30 _diffrn_standards_decay_% 0 _diffrn_standards_interval_count 150 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu 0.517 _exptl_absorpt_correction_T_max 0.9539 _exptl_absorpt_correction_T_min 0.9158 _exptl_absorpt_correction_type 'Analytical, 6 faces indexed' _exptl_crystal_colour Colourless _exptl_crystal_density_diffrn 1.544 _exptl_crystal_description 'Tetragonal prism' _exptl_crystal_F_000 272 _exptl_crystal_size_max 0.48 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.11 _refine_diff_density_max 0.522 _refine_diff_density_min -0.494 _refine_ls_abs_structure_details 'Flack (1983)' _refine_ls_abs_structure_Flack -0.07(14) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_all 1.061 _refine_ls_goodness_of_fit_obs 1.072 _refine_ls_hydrogen_treatment 'Hatoms: geom, riding, rigid-body' _refine_ls_matrix_type full _refine_ls_number_parameters 149 _refine_ls_number_reflns 1116 _refine_ls_number_restraints 1 _refine_ls_restrained_S_all 1.162 _refine_ls_restrained_S_obs 1.071 _refine_ls_R_factor_all 0.0423 _refine_ls_R_factor_obs 0.0341 _refine_ls_shift/esd_max 0.000 _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^)+(0.0491P)^2^+0.5576P] where P = (F~o~^2^+2F~c~^2^)/3 ; _refine_ls_wR_factor_all 0.1033 _refine_ls_wR_factor_obs 0.0905 _reflns_number_observed 1022 _reflns_number_total 1118 _reflns_observed_criterion >2\s(I) _cod_data_source_file hu1109.cif _cod_data_source_block 1 _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_sg_symbol_Hall 'P 2y1' _cod_original_sg_symbol_H-M 'P 21' _cod_original_formula_sum 'C10 H11 Cl1 O4 S1' _cod_database_code 2010196 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' 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 0.0366(7) 0.0334(7) 0.0218(5) -0.0006(6) 0.0123(5) -0.0059(5) S 0.0159(5) 0.0211(6) 0.0159(5) -0.0001(5) 0.0073(4) 0.0003(5) O1 0.0179(15) 0.024(2) 0.0157(14) -0.0031(14) 0.0070(11) 0.0002(14) O2 0.024(2) 0.020(2) 0.0233(15) -0.0038(15) 0.0108(13) -0.0011(15) O3 0.0187(15) 0.032(2) 0.024(2) 0.0058(15) 0.0119(13) 0.0025(15) O4 0.026(2) 0.029(2) 0.026(2) -0.007(2) 0.0087(13) 0.000(2) C1 0.017(2) 0.028(3) 0.011(2) -0.005(2) 0.005(2) -0.002(2) C2 0.018(2) 0.028(3) 0.018(2) -0.002(2) 0.009(2) 0.000(2) C3 0.020(2) 0.018(3) 0.020(2) -0.001(2) 0.007(2) -0.003(2) C4 0.024(2) 0.025(3) 0.015(2) -0.001(2) 0.005(2) -0.004(2) C5 0.024(2) 0.040(3) 0.017(2) -0.004(3) 0.010(2) 0.002(2) C6 0.016(2) 0.031(3) 0.022(2) -0.007(2) 0.010(2) 0.000(2) C7 0.041(3) 0.035(3) 0.023(2) 0.000(3) 0.013(2) -0.001(3) C8 0.017(2) 0.030(3) 0.023(2) -0.004(2) 0.007(2) 0.001(2) C9 0.019(2) 0.020(3) 0.017(2) 0.000(2) 0.004(2) 0.002(2) C10 0.026(2) 0.031(3) 0.019(2) -0.001(2) 0.011(2) -0.005(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 Cl 0.17189(11) 0.2010(3) 0.04095(10) 0.0302(3) Uani d . 1 . Cl S 0.21188(10) 0.9788(2) 0.46500(9) 0.0172(3) Uani d . 1 . S O1 0.1747(3) 0.8044(7) 0.3369(3) 0.0189(7) Uani d . 1 . O O2 0.2973(3) 1.1728(7) 0.4447(3) 0.0217(7) Uani d . 1 . O O3 0.0927(3) 1.0568(7) 0.4827(3) 0.0238(8) Uani d . 1 . O O4 -0.0181(3) 0.2578(8) 0.1743(3) 0.0269(8) Uani d . 1 . O C1 0.3006(4) 0.7649(10) 0.5913(4) 0.0191(10) Uani d . 1 . C C2 0.4303(4) 0.7003(11) 0.6077(4) 0.0202(10) Uani d . 1 . C H2 0.4720(4) 0.7783(11) 0.5538(4) 0.024 Uiso calc R 1 . H C3 0.4966(4) 0.5219(9) 0.7032(4) 0.0196(10) Uani d . 1 . C H3 0.5846(4) 0.4762(9) 0.7143(4) 0.024 Uiso calc R 1 . H C4 0.4373(4) 0.4061(10) 0.7843(4) 0.0220(11) Uani d . 1 . C C5 0.3094(4) 0.4787(13) 0.7670(4) 0.0262(10) Uani d . 1 . C H5 0.2687(4) 0.4050(13) 0.8226(4) 0.031 Uiso calc R 1 . H C6 0.2398(4) 0.6541(10) 0.6716(4) 0.0223(11) Uani d . 1 . C H6 0.1517(4) 0.6992(10) 0.6606(4) 0.027 Uiso calc R 1 . H C7 0.5105(5) 0.2046(12) 0.8853(4) 0.0325(12) Uani d . 1 . C H7C 0.6029(10) 0.257(4) 0.927(3) 0.050(10) Uiso calc R 1 . H H7B 0.506(3) 0.0337(19) 0.8427(7) 0.050(10) Uiso calc R 1 . H H7A 0.471(2) 0.192(5) 0.9524(19) 0.050(10) Uiso calc R 1 . H C8 0.0625(4) 0.6268(11) 0.3077(4) 0.0233(11) Uani d . 1 . C H8B -0.0205(4) 0.7286(11) 0.2739(4) 0.043(12) Uiso calc R 1 . H H8A 0.0658(4) 0.5363(11) 0.3890(4) 0.043(12) Uiso calc R 1 . H C9 0.0649(4) 0.4267(10) 0.2068(4) 0.0194(10) Uani d . 1 . C C10 0.1729(4) 0.4601(12) 0.1503(4) 0.0246(11) Uani d . 1 . C H10B 0.2595(4) 0.4648(12) 0.2230(4) 0.031(10) Uiso calc R 1 . H H10A 0.1606(4) 0.6295(12) 0.1030(4) 0.031(10) Uiso calc R 1 . H 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' Cl Cl 0.1484 0.1585 '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 120.1(2) yes O2 S O1 102.9(2) yes O3 S O1 108.6(2) yes O2 S C1 110.4(2) ? O3 S C1 109.6(2) ? O1 S C1 103.8(2) yes C8 O1 S 117.9(3) yes C6 C1 C2 120.8(4) yes C6 C1 S 119.7(3) ? C2 C1 S 119.6(3) ? C3 C2 C1 118.9(4) ? C2 C3 C4 121.5(4) ? C5 C4 C3 118.1(4) ? C5 C4 C7 121.4(4) ? C3 C4 C7 120.5(4) ? C6 C5 C4 122.0(4) ? C5 C6 C1 118.8(4) ? O1 C8 C9 110.1(3) yes O4 C9 C8 119.3(4) yes O4 C9 C10 124.6(4) yes C8 C9 C10 116.1(4) yes C9 C10 Cl 111.8(4) yes 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 Cl C10 . 1.778(5) yes S O2 . 1.428(3) yes S O3 . 1.436(3) yes S O1 . 1.582(3) yes S C1 . 1.750(5) yes O1 C8 . 1.460(5) yes O4 C9 . 1.205(6) yes C1 C6 . 1.396(6) ? C1 C2 . 1.397(6) ? C2 C3 . 1.375(7) ? C3 C4 . 1.401(6) ? C4 C5 . 1.386(6) ? C4 C7 . 1.507(7) ? C5 C6 . 1.374(7) ? C8 C9 . 1.509(7) yes C9 C10 . 1.522(6) 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 75.4(4) yes C1 S O1 C8 80.3(3) yes S O1 C8 C9 -164.2(3) yes O1 C8 C9 C10 -4.2(6) yes C8 C9 C10 Cl 176.2(3) yes loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 ChemSpider 21139258 2 PubChem 15642852