#------------------------------------------------------------------------------ #$Date: 2025-08-18 23:52:38 +0100 (Mon, 18 Aug 2025) $ #$Revision: 301791 $ #$URL: svn://www.crystallography.net/cod/cif/2/00/65/2006523.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_2006523 loop_ _publ_author_name 'Jeyaraman, Jeyakanthan' 'Velmurugan, D.' _publ_section_title ; 4-Chlorophenyl 2,6-Dimethylphenyl Sulfone ; _journal_issue 9 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first 1344 _journal_page_last 1345 _journal_paper_doi 10.1107/S0108270197005714 _journal_volume 53 _journal_year 1997 _chemical_formula_structural 'C14 H13 Cl O2 S' _chemical_formula_sum 'C14 H13 Cl O2 S' _chemical_formula_weight 280.75 _chemical_name_systematic '4-Chlorophenyl-2,6-dimethyl phenylsulphone' _space_group_IT_number 15 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-C 2yc' _symmetry_space_group_name_H-M 'C 1 2/c 1' _audit_creation_method SHELXL _cell_angle_alpha 90.00 _cell_angle_beta 126.580(11) _cell_angle_gamma 90.00 _cell_formula_units_Z 8 _cell_length_a 20.239(5) _cell_length_b 10.911(2) _cell_length_c 15.197(6) _cell_measurement_reflns_used 25 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 18 _cell_measurement_theta_min 14 _cell_volume 2694.9(14) _computing_cell_refinement 'MSC/AFC Diffractometer Control Software' _computing_data_collection ;MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1988) ; _computing_data_reduction 'MSC/AFC Diffractometer Control Software' _computing_molecular_graphics 'ORTEP92 (Vickovi\'c, 1994)' _computing_publication_material 'PARST (Nardelli, 1983)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1985)' _diffrn_ambient_temperature 293(2) _diffrn_measurement_device 'Rigaku AFC-7S diffractometer' _diffrn_measurement_method \w/2\q _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71069 _diffrn_reflns_av_R_equivalents 0.0325 _diffrn_reflns_av_sigmaI/netI 0.0302 _diffrn_reflns_limit_h_max 24 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_number 2934 _diffrn_reflns_theta_max 25.02 _diffrn_reflns_theta_min 2.25 _diffrn_standards_decay_% <1 _diffrn_standards_interval_count 100 _diffrn_standards_interval_time 60 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu 0.429 _exptl_absorpt_correction_type none _exptl_crystal_colour Transparent _exptl_crystal_density_diffrn 1.384 _exptl_crystal_density_method 'not measured' _exptl_crystal_description 'Rectangular block' _exptl_crystal_F_000 1168 _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.15 _refine_diff_density_max 0.29 _refine_diff_density_min -0.32 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_all 1.056 _refine_ls_goodness_of_fit_obs 1.118 _refine_ls_hydrogen_treatment 'H atoms refined' _refine_ls_matrix_type fullcycle _refine_ls_number_parameters 215 _refine_ls_number_reflns 2367 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.056 _refine_ls_restrained_S_obs 1.118 _refine_ls_R_factor_all 0.0712 _refine_ls_R_factor_obs .0513 _refine_ls_shift/esd_max 0.067 _refine_ls_shift/esd_mean 0.007 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^)+(0.0666P)^2^+4.2184P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_all 0.1532 _refine_ls_wR_factor_obs .1371 _reflns_number_observed 1744 _reflns_number_total 2367 _reflns_observed_criterion >2sigma(I) _cod_data_source_file mu1313.cif _cod_data_source_block JEY _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. '_geom_bond_publ_flag' value 'YES' changed to 'yes' according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29 (5 times). Automatic conversion script Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius ; _cod_original_cell_volume 2694.8(14) _cod_original_sg_symbol_H-M 'C 2/c' _cod_database_code 2006523 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -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 S1 .0560(2) .0491(3) .0665(3) -.0029(2) .0398(2) -.0031(2) Cl .1026(5) .0744(5) .1231(6) -.0377(4) .0525(5) -.0133(4) O1 .0494(7) .0729(12) .0951(11) .0000(8) .0404(7) -.0104(9) O2 .1011(9) .0611(11) .0815(9) -.0083(9) .0664(7) -.0007(8) C1 .0483(9) .0528(13) .0628(11) -.0078(9) .0333(8) -.0116(10) C2 .0524(10) .086(2) .0554(11) -.0117(12) .0296(9) -.0097(12) C3 .0762(14) .128(3) .0676(13) -.016(2) .0449(11) -.024(2) C4 .0842(14) .128(3) .098(2) -.022(2) .0613(12) -.053(2) C5 .0706(13) .068(2) .119(2) -.0084(13) .0563(13) -.029(2) C6 .0561(10) .0509(13) .0861(14) -.0087(10) .0432(10) -.0138(11) C7 .098(2) .059(2) .135(2) .0134(14) .0783(15) .024(2) C8 .085(2) .105(2) .0714(14) .005(2) .0443(12) .025(2) C1' .0511(9) .0440(12) .0587(11) -.0024(9) .0307(8) -.0001(9) C2' .0577(11) .0512(14) .0719(13) .0030(11) .0317(10) .0087(11) C3' .0804(14) .0448(13) .083(2) .0003(12) .0436(12) .0060(12) C4' .0705(13) .0556(15) .0759(14) -.0159(12) .0391(11) -.0043(12) C5' .0549(13) .067(2) .091(2) .0000(13) .0275(13) -.0008(15) C6' .0575(12) .0494(14) .083(2) .0025(11) .0291(11) .0003(12) 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 H3 .1735(18) .097(3) 1.072(3) .123(11) Uiso d . 1 . H H4 .1026(17) .285(3) 1.005(2) .121(11) Uiso d . 1 . H H71 .0774(15) .266(3) .649(2) .098(9) Uiso d . 1 . H H72 .1584(15) .335(3) .724(2) .085(8) Uiso d . 1 . H H73 .0754(17) .383(3) .697(2) .118(11) Uiso d . 1 . H H81 .2019(16) -.110(3) .949(2) .096(9) Uiso d . 1 . H H82 .2302(15) -.059(3) 1.059(2) .087(9) Uiso d . 1 . H H83 .2843(17) -.043(3) 1.022(2) .119(11) Uiso d . 1 . H H9 .0806(16) .375(3) .842(2) .096(10) Uiso d . 1 . H H2' .2143(13) -.215(3) .7964(18) .070(8) Uiso d . 1 . H H3' .1185(14) -.381(2) .707(2) .079(8) Uiso d . 1 . H H5' -.0695(17) -.137(3) .558(2) .104(10) Uiso d . 1 . H H6' .0289(15) .025(3) .636(2) .084(8) Uiso d . 1 . H S1 .19806(3) .04551(6) .78069(5) .0552(2) Uani d . 1 . S Cl -.04933(5) -.39136(8) .56848(8) .1091(4) Uani d . 1 . Cl O1 .27978(9) -.0011(2) .8559(2) .0741(6) Uani d . 1 . O O2 .18181(11) .1154(2) .68955(14) .0739(5) Uani d . 1 . O C1 .16865(12) .1294(2) .8527(2) .0545(6) Uani d . 1 . C C2 .18459(14) .0757(3) .9481(2) .0660(7) Uani d . 1 . C C3 .1589(2) .1382(4) 1.0024(2) .0892(10) Uani d . 1 . C C4 .1208(2) .2493(4) .9663(3) .0993(11) Uani d . 1 . C C5 .1061(2) .3011(3) .8745(3) .0863(10) Uani d . 1 . C C6 .12948(13) .2438(2) .8137(2) .0638(7) Uani d . 1 . C C7 .1103(2) .3109(3) .7148(3) .0917(10) Uani d . 1 . C C8 .2276(2) -.0448(3) .9968(2) .0884(10) Uani d . 1 . C C1' .12839(13) -.0798(2) .7248(2) .0525(6) Uani d . 1 . C C2' .15767(14) -.1986(2) .7486(2) .0645(7) Uani d . 1 . C C3' .1031(2) -.2949(2) .7007(2) .0726(8) Uani d . 1 . C C4' .0204(2) -.2713(3) .6303(2) .0701(8) Uani d . 1 . C C5' -.0092(2) -.1529(3) .6048(3) .0809(10) Uani d . 1 . C C6' .0452(2) -.0570(2) .6526(2) .0710(8) Uani d . 1 . C 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' Cl Cl 0.1484 0.1585 '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' O O 0.0106 0.0060 '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' 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 O1 S1 O2 116.76(12) yes O1 S1 C1' 108.61(11) yes O2 S1 C1' 106.69(11) yes O1 S1 C1 110.04(11) yes O2 S1 C1 110.56(12) yes C1' S1 C1 103.24(12) yes C6 C1 C2 121.8(3) ? C6 C1 S1 120.6(2) yes C2 C1 S1 117.6(2) yes C3 C2 C1 118.0(3) ? C3 C2 C8 116.6(3) ? C1 C2 C8 125.4(3) ? C4 C3 C2 121.3(3) ? C4 C3 H3 124.(2) ? C2 C3 H3 115.(2) ? C5 C4 C3 120.4(3) ? C5 C4 H4 122.4(19) ? C3 C4 H4 117.1(19) ? C4 C5 C6 122.2(3) ? C4 C5 H9 128.(2) ? C6 C5 H9 109.(2) ? C1 C6 C5 116.3(3) ? C1 C6 C7 126.8(3) ? C5 C6 C7 116.9(3) ? C6 C7 H71 114.1(19) ? C6 C7 H72 111.2(15) ? H71 C7 H72 109.(3) ? C6 C7 H73 112.(2) ? H71 C7 H73 101.(2) ? H72 C7 H73 109.(3) ? C2 C8 H81 113.3(16) ? C2 C8 H82 108.2(18) ? H81 C8 H82 109.(3) ? C2 C8 H83 112.(2) ? H81 C8 H83 108.(3) ? H82 C8 H83 105.(2) ? C6' C1' C2' 120.5(2) ? C6' C1' S1 119.2(2) yes C2' C1' S1 120.2(2) yes C3' C2' C1' 119.6(2) ? C3' C2' H2' 119.5(17) ? C1' C2' H2' 120.8(17) ? C4' C3' C2' 119.4(2) ? C4' C3' H3' 115.3(14) ? C2' C3' H3' 125.1(14) ? C3' C4' C5' 121.3(2) ? C3' C4' Cl 120.1(2) yes C5' C4' Cl 118.6(2) yes C6' C5' C4' 119.3(2) ? C6' C5' H5' 119.9(18) ? C4' C5' H5' 120.6(18) ? C5' C6' C1' 119.9(2) ? C5' C6' H6' 122.9(15) ? C1' C6' H6' 117.2(15) ? 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 O1 . 1.431(2) yes S1 O2 . 1.437(2) yes S1 C1' . 1.775(2) yes S1 C1 . 1.779(3) yes Cl C4' . 1.734(3) yes C1 C6 . 1.406(3) ? C1 C2 . 1.411(4) ? C2 C3 . 1.389(5) ? C2 C8 . 1.505(4) ? C3 C4 . 1.364(5) ? C4 C5 . 1.363(5) ? C5 C6 . 1.410(5) ? C6 C7 . 1.500(4) ? C1' C6' . 1.378(3) ? C1' C2' . 1.382(3) ? C2' C3' . 1.376(4) ? C3' C4' . 1.371(4) ? C4' C5' . 1.379(4) ? C5' C6' . 1.372(4) ? 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 O1 S1 C1 C6 134.9(2) O2 S1 C1 C6 4.4(2) C1' S1 C1 C6 -109.3(2) O1 S1 C1 C2 -46.4(2) O2 S1 C1 C2 -176.8(2) C1' S1 C1 C2 69.4(2) C6 C1 C2 C3 1.2(3) S1 C1 C2 C3 -177.5(2) C6 C1 C2 C8 -178.7(2) S1 C1 C2 C8 2.6(3) C1 C2 C3 C4 -1.2(4) C8 C2 C3 C4 178.7(3) C2 C3 C4 C5 0.7(5) C3 C4 C5 C6 -0.3(5) C2 C1 C6 C5 -0.8(3) S1 C1 C6 C5 177.9(2) C2 C1 C6 C7 179.1(2) S1 C1 C6 C7 -2.2(3) C4 C5 C6 C1 0.3(4) C4 C5 C6 C7 -179.6(3) O1 S1 C1' C6' 177.7(2) O2 S1 C1' C6' -55.6(3) C1 S1 C1' C6' 60.9(3) O1 S1 C1' C2' -6.0(3) O2 S1 C1' C2' 120.7(2) C1 S1 C1' C2' -122.8(2) C6' C1' C2' C3' -0.8(5) S1 C1' C2' C3' -177.0(2) C1' C2' C3' C4' -0.3(5) C2' C3' C4' C5' 1.3(5) C2' C3' C4' Cl 179.6(3) C3' C4' C5' C6' -1.3(5) Cl C4' C5' C6' -179.7(3) C4' C5' C6' C1' 0.3(5) C2' C1' C6' C5' 0.8(5) S1 C1' C6' C5' 177.0(3) loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 ChemSpider 21137520 2 PubChem 85746329