#------------------------------------------------------------------------------ #$Date: 2025-08-23 00:36:08 +0100 (Sat, 23 Aug 2025) $ #$Revision: 301880 $ #$URL: svn://www.crystallography.net/cod/cif/8/10/16/8101681.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_8101681 loop_ _publ_author_name 'M.-C. Liu' 'J.-C. Ding' 'W. Feng' 'H.-Y. Wu' _publ_section_title ; Crystal structure of phenylbenzylsulfone, (C~6~H~5~)(C~7~H~7~)SO~2~ ; _journal_issue 1 _journal_name_full 'Zeitschrift f\"ur Kristallographie - New Crystal Structures' _journal_page_first 23 _journal_page_last 24 _journal_volume 220 _journal_year 2005 _chemical_formula_moiety (C6H5)SO2(C7H7) _chemical_formula_sum 'C13 H12 O2 S' _chemical_formula_weight 232.29 _chemical_name_systematic ; Phenylbenzylsulfone ; _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 SHELXL-97 _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 16.5888(6) _cell_length_b 12.2537(5) _cell_length_c 5.6054(2) _cell_measurement_reflns_used 3233 _cell_measurement_temperature 298(2) _cell_measurement_theta_max 25.18 _cell_measurement_theta_min 2.45 _cell_volume 1139.43(7) _computing_cell_refinement 'SAINT (Siemens, 1997)' _computing_data_collection 'SMART (Siemens, 1997)' _computing_data_reduction 'SAINT (Siemens, 1997)' _computing_molecular_graphics 'ORTEP-II (Johnson, 1976)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _diffrn_ambient_temperature 298(2) _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measurement_device_type 'Bruker SMART APEX CCD' _diffrn_measurement_method '600 frames, delta omega = 0.3 dgr' _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 0.0239 _diffrn_reflns_av_sigmaI/netI 0.0251 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_l_max 6 _diffrn_reflns_limit_l_min -6 _diffrn_reflns_number 5861 _diffrn_reflns_theta_full 25.18 _diffrn_reflns_theta_max 25.18 _diffrn_reflns_theta_min 2.07 _diffrn_standards_decay_% 0 _diffrn_standards_interval_time 0 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.265 _exptl_absorpt_correction_T_max 0.9490 _exptl_absorpt_correction_T_min 0.9038 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS (Bruker, 2002)' _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.354 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 488 _exptl_crystal_size_max 0.39 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.20 _refine_diff_density_max 0.379 _refine_diff_density_min -0.241 _refine_diff_density_rms 0.053 _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.06(16) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.322 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 145 _refine_ls_number_reflns 1978 _refine_ls_number_restraints 1 _refine_ls_restrained_S_all 1.322 _refine_ls_R_factor_all 0.0595 _refine_ls_R_factor_gt 0.0591 _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^)+(0.0312P)^2^+1.0715P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1276 _refine_ls_wR_factor_ref 0.1278 _reflns_number_gt 1965 _reflns_number_total 1978 _reflns_threshold_expression I>2\sigma(I) _cod_data_source_file 1267-1408.cff _cod_data_source_block mc _cod_depositor_comments ; The following automatic conversions were performed: '_exptl_absorpt_correction_type' value 'Multi-scan' changed to 'multi-scan' 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 1555 2011-01-17 13:19:09Z saulius ; _cod_original_sg_symbol_Hall P2c-2n _cod_original_sg_symbol_H-M Pna21 _cod_database_code 8101681 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' 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_Wyckoff_symbol _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S1 S 0.09785(6) 0.11027(7) 0.4039(2) 0.0425(3) Uani 1 4 a d . . . O1 O 0.0818(2) 0.1094(2) 0.6556(6) 0.0558(9) Uani 1 4 a d . . . O2 O 0.1316(2) 0.0140(2) 0.2968(7) 0.0649(10) Uani 1 4 a d . . . C1 C 0.1673(2) 0.3049(3) 0.5080(9) 0.0436(10) Uani 1 4 a d . . . H1 H 0.1355 0.3033 0.6446 0.052 Uiso 1 4 a calc R . . C2 C 0.2197(3) 0.3900(4) 0.4703(8) 0.0542(14) Uani 1 4 a d . . . H2 H 0.2246 0.4451 0.5833 0.065 Uiso 1 4 a calc R . . C3 C 0.2651(3) 0.3932(4) 0.2629(10) 0.0571(13) Uani 1 4 a d . . . H3 H 0.2997 0.4514 0.2343 0.068 Uiso 1 4 a calc R . . C4 C 0.2589(3) 0.3102(4) 0.1004(9) 0.0601(13) Uani 1 4 a d . . . H4 H 0.2899 0.3124 -0.0378 0.072 Uiso 1 4 a calc R . . C5 C 0.2074(3) 0.2234(4) 0.1380(8) 0.0489(11) Uani 1 4 a d . . . H5 H 0.2034 0.1671 0.0275 0.059 Uiso 1 4 a calc R . . C6 C 0.1621(2) 0.2228(3) 0.3446(7) 0.0364(9) Uani 1 4 a d . . . C7 C 0.0058(3) 0.1390(3) 0.2490(9) 0.0467(11) Uani 1 4 a d . . . H7A H 0.0168 0.1405 0.0790 0.056 Uiso 1 4 a calc R . . H7B H -0.0319 0.0800 0.2785 0.056 Uiso 1 4 a calc R . . C8 C -0.0335(2) 0.2450(3) 0.3186(8) 0.0403(10) Uani 1 4 a d . . . C9 C -0.0251(3) 0.3356(4) 0.1769(9) 0.0512(11) Uani 1 4 a d . . . H9 H 0.0061 0.3317 0.0394 0.061 Uiso 1 4 a calc R . . C10 C -0.0625(3) 0.4329(4) 0.2361(11) 0.0641(15) Uani 1 4 a d . . . H10 H -0.0561 0.4938 0.1390 0.077 Uiso 1 4 a calc R . . C11 C -0.1085(3) 0.4393(4) 0.4362(12) 0.0656(15) Uani 1 4 a d . . . H11 H -0.1348 0.5041 0.4742 0.079 Uiso 1 4 a calc R . . C12 C -0.1161(3) 0.3497(4) 0.5822(9) 0.0598(13) Uani 1 4 a d . . . H12 H -0.1465 0.3546 0.7213 0.072 Uiso 1 4 a calc R . . C13 C -0.0790(2) 0.2525(4) 0.5239(10) 0.0505(11) Uani 1 4 a d . . . H13 H -0.0846 0.1921 0.6231 0.061 Uiso 1 4 a 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 0.0499(6) 0.0294(4) 0.0484(6) 0.0048(5) -0.0042(5) 0.0002(4) O1 0.062(2) 0.0472(19) 0.058(2) 0.0188(16) -0.0042(16) -0.0095(14) O2 0.076(2) 0.0321(15) 0.086(3) -0.0025(16) -0.007(2) 0.0077(15) C1 0.043(2) 0.040(2) 0.048(2) -0.001(2) 0.004(2) -0.0086(18) C2 0.052(3) 0.054(3) 0.056(4) -0.009(2) -0.007(2) -0.005(2) C3 0.045(3) 0.049(3) 0.076(4) 0.014(3) -0.005(3) -0.006(2) C4 0.051(3) 0.077(3) 0.052(3) 0.017(3) 0.009(2) 0.000(3) C5 0.061(3) 0.045(2) 0.041(3) 0.000(2) 0.004(2) 0.006(2) C6 0.033(2) 0.0368(19) 0.039(3) 0.0034(17) -0.0079(16) 0.0029(15) C7 0.047(2) 0.037(2) 0.056(3) -0.006(2) -0.014(2) -0.0070(19) C8 0.035(2) 0.041(2) 0.045(2) -0.0002(18) -0.0086(18) -0.0079(17) C9 0.050(2) 0.059(3) 0.045(3) 0.009(2) 0.002(2) 0.006(2) C10 0.067(3) 0.048(3) 0.078(4) 0.018(3) 0.001(3) 0.004(2) C11 0.056(3) 0.057(3) 0.084(5) -0.010(3) 0.001(3) 0.013(2) C12 0.051(3) 0.081(4) 0.047(3) -0.006(3) 0.009(2) 0.007(3) C13 0.044(2) 0.055(3) 0.053(3) 0.010(3) 0.003(2) -0.008(2) 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' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 S1 O2 118.4(2) . . ? O1 S1 C6 107.52(18) . . ? O2 S1 C6 109.0(2) . . ? O1 S1 C7 108.7(2) . . ? O2 S1 C7 106.9(2) . . ? C6 S1 C7 105.57(19) . . ? C6 C1 C2 119.8(4) . . ? C6 C1 H1 120.1 . . ? C2 C1 H1 120.1 . . ? C1 C2 C3 119.7(4) . . ? C1 C2 H2 120.2 . . ? C3 C2 H2 120.2 . . ? C4 C3 C2 119.7(4) . . ? C4 C3 H3 120.1 . . ? C2 C3 H3 120.1 . . ? C3 C4 C5 121.2(5) . . ? C3 C4 H4 119.4 . . ? C5 C4 H4 119.4 . . ? C4 C5 C6 118.0(4) . . ? C4 C5 H5 121.0 . . ? C6 C5 H5 121.0 . . ? C1 C6 C5 121.7(4) . . ? C1 C6 S1 119.1(3) . . ? C5 C6 S1 119.2(3) . . ? C8 C7 S1 114.4(3) . . ? C8 C7 H7A 108.7 . . ? S1 C7 H7A 108.7 . . ? C8 C7 H7B 108.7 . . ? S1 C7 H7B 108.7 . . ? H7A C7 H7B 107.6 . . ? C9 C8 C13 118.9(4) . . ? C9 C8 C7 120.3(4) . . ? C13 C8 C7 120.8(4) . . ? C8 C9 C10 120.9(5) . . ? C8 C9 H9 119.6 . . ? C10 C9 H9 119.6 . . ? C11 C10 C9 120.0(5) . . ? C11 C10 H10 120.0 . . ? C9 C10 H10 120.0 . . ? C10 C11 C12 119.7(4) . . ? C10 C11 H11 120.1 . . ? C12 C11 H11 120.1 . . ? C11 C12 C13 120.5(5) . . ? C11 C12 H12 119.8 . . ? C13 C12 H12 119.8 . . ? C8 C13 C12 120.0(5) . . ? C8 C13 H13 120.0 . . ? C12 C13 H13 120.0 . . ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 O1 1.436(3) . ? S1 O2 1.437(3) . ? S1 C6 1.774(4) . ? S1 C7 1.791(4) . ? C1 C6 1.363(6) . ? C1 C2 1.374(6) . ? C1 H1 0.9300 . ? C2 C3 1.386(7) . ? C2 H2 0.9300 . ? C3 C4 1.369(7) . ? C3 H3 0.9300 . ? C4 C5 1.380(6) . ? C4 H4 0.9300 . ? C5 C6 1.381(6) . ? C5 H5 0.9300 . ? C7 C8 1.504(6) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 C9 1.373(6) . ? C8 C13 1.379(6) . ? C9 C10 1.384(7) . ? C9 H9 0.9300 . ? C10 C11 1.359(8) . ? C10 H10 0.9300 . ? C11 C12 1.376(7) . ? C11 H11 0.9300 . ? C12 C13 1.380(7) . ? C12 H12 0.9300 . ? C13 H13 0.9300 . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A C7 H7B O1 0.97 2.56 3.413(5) 147.0 2_554 C1 H1 O1 0.93 2.54 2.904(5) 103.8 . loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 ChemSpider 69027 2 PubChem 76561