#------------------------------------------------------------------------------ #$Date: 2025-08-19 11:43:10 +0100 (Tue, 19 Aug 2025) $ #$Revision: 301803 $ #$URL: svn://www.crystallography.net/cod/cif/2/20/21/2202151.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_2202151 loop_ _publ_author_name 'Nagarajan Vembu' 'Maruthai Nallu' 'Jered Garrison' 'Wiley J. Youngs' _publ_section_title ; 2-Chlorophenyl 4-toluenesulfonate: molecular aggregration through weak C---H···O interactions ; _journal_issue 4 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o503 _journal_page_last o505 _journal_paper_doi 10.1107/S1600536803005841 _journal_volume 59 _journal_year 2003 _chemical_formula_iupac 'C13 H11 Cl O3 S' _chemical_formula_moiety 'C13 H11 Cl O3 S' _chemical_formula_sum 'C13 H11 Cl O3 S' _chemical_formula_weight 282.73 _chemical_melting_point 72.5(5) _chemical_name_common '2-chlorophenyl p-toluenesulfonate' _chemical_name_systematic ; 2-chlorophenyl 4-toluenesulfonate ; _space_group_IT_number 2 _symmetry_cell_setting triclinic _symmetry_space_group_name_Hall '-P 1' _symmetry_space_group_name_H-M 'P -1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-97 _cell_angle_alpha 95.378(6) _cell_angle_beta 97.886(6) _cell_angle_gamma 96.404(6) _cell_formula_units_Z 2 _cell_length_a 7.487(3) _cell_length_b 8.675(4) _cell_length_c 10.277(4) _cell_measurement_reflns_used 1959 _cell_measurement_temperature 100(2) _cell_measurement_theta_max 26.71 _cell_measurement_theta_min 2.38 _cell_volume 653.0(5) _computing_cell_refinement SMART _computing_data_collection 'SMART-NT (Bruker, 1998)' _computing_data_reduction 'SAINT-NT (Bruker, 1998)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 1998)' _computing_publication_material SHELXTL _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _diffrn_ambient_temperature 100(2) _diffrn_measurement_device_type 'Bruker SMART CCD area-detector' _diffrn_measurement_method '\f and \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 0.0271 _diffrn_reflns_av_sigmaI/netI 0.0451 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_number 4385 _diffrn_reflns_theta_max 24.99 _diffrn_reflns_theta_min 2.01 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.448 _exptl_absorpt_correction_T_max 0.9565 _exptl_absorpt_correction_T_min 0.8410 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SADABS; Sheldrick, 1995)' _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.438 _exptl_crystal_density_method 'not measured' _exptl_crystal_description needle _exptl_crystal_F_000 292 _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _refine_diff_density_max 0.485 _refine_diff_density_min -0.344 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.020 _refine_ls_hydrogen_treatment refall _refine_ls_matrix_type full _refine_ls_number_parameters 207 _refine_ls_number_reflns 2227 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.020 _refine_ls_R_factor_all 0.0485 _refine_ls_R_factor_gt 0.0377 _refine_ls_shift/su_max <0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w = 1/[\s^2^(Fo^2^)+(0.0594P)^2^] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0933 _refine_ls_wR_factor_ref 0.0960 _reflns_number_gt 1762 _reflns_number_total 2227 _reflns_threshold_expression I>2\s(I) _cod_data_source_file om6135.cif _cod_data_source_block I _cod_depositor_comments ; The following automatic conversions were performed: '_chemical_melting_point' value '72-73' was changed to '72.5(5)' - the average value was taken and precision was estimated. Automatic conversion script Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana The following automatic conversions were performed: '_chemical_melting_point' value '72-73' was changed to '72.5(5)' - the average value was taken and precision was estimated. Automatic conversion script Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana ; _cod_database_code 2202151 _cod_database_fobs_code 2202151 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_type_symbol S 0.33885(7) 0.50916(6) 0.19595(5) 0.02342(18) Uani d . 1 . . S Cl 0.51020(8) 0.96080(6) 0.32565(5) 0.03011(19) Uani d . 1 . . Cl O1 0.2264(2) 0.42744(16) 0.07871(15) 0.0290(4) Uani d . 1 . . O O2 0.4723(2) 0.43083(17) 0.27041(15) 0.0299(4) Uani d . 1 . . O O3 0.46129(19) 0.65838(17) 0.15408(14) 0.0247(4) Uani d . 1 . . O C1 -0.1413(4) 0.8042(3) 0.5581(3) 0.0342(6) Uani d . 1 . . C C2 -0.0217(3) 0.7296(2) 0.4682(2) 0.0241(5) Uani d . 1 . . C C3 -0.0817(3) 0.6964(3) 0.3311(2) 0.0260(5) Uani d . 1 . . C C4 0.0267(3) 0.6280(2) 0.2466(2) 0.0237(5) Uani d . 1 . . C C5 0.1981(3) 0.5938(2) 0.3013(2) 0.0213(5) Uani d . 1 . . C C6 0.2619(3) 0.6262(2) 0.4372(2) 0.0243(5) Uani d . 1 . . C C7 0.1507(3) 0.6940(2) 0.5196(2) 0.0262(5) Uani d . 1 . . C C8 0.3708(3) 0.7764(2) 0.0934(2) 0.0207(5) Uani d . 1 . . C C9 0.2782(3) 0.7476(3) -0.0355(2) 0.0264(5) Uani d . 1 . . C C10 0.1998(3) 0.8697(3) -0.0928(2) 0.0301(6) Uani d . 1 . . C C11 0.2183(3) 1.0190(3) -0.0221(2) 0.0301(6) Uani d . 1 . . C C12 0.3130(3) 1.0465(3) 0.1056(2) 0.0270(5) Uani d . 1 . . C C13 0.3888(3) 0.9243(3) 0.1646(2) 0.0235(5) Uani d . 1 . . C H1A -0.130(4) 0.764(3) 0.647(3) 0.057(9) Uiso d . 1 . . H H1B -0.276(4) 0.774(3) 0.524(3) 0.065(9) Uiso d . 1 . . H H1C -0.113(4) 0.906(4) 0.571(3) 0.061(10) Uiso d . 1 . . H H3 -0.201(3) 0.719(2) 0.294(2) 0.023(6) Uiso d . 1 . . H H4 -0.015(3) 0.609(3) 0.160(2) 0.025(6) Uiso d . 1 . . H H6 0.378(3) 0.605(2) 0.475(2) 0.018(5) Uiso d . 1 . . H H7 0.203(3) 0.714(3) 0.613(2) 0.025(6) Uiso d . 1 . . H H9 0.268(3) 0.642(3) -0.087(2) 0.027(6) Uiso d . 1 . . H H10 0.129(3) 0.849(3) -0.181(2) 0.025(6) Uiso d . 1 . . H H11 0.164(3) 1.098(3) -0.063(2) 0.030(6) Uiso d . 1 . . H H12 0.335(3) 1.149(3) 0.152(2) 0.034(7) Uiso d . 1 . . H 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 S 0.0263(3) 0.0142(3) 0.0299(3) 0.0068(2) 0.0057(2) -0.0042(2) Cl 0.0373(4) 0.0229(3) 0.0275(3) 0.0019(2) 0.0036(2) -0.0074(2) O1 0.0341(9) 0.0152(8) 0.0353(9) 0.0029(7) 0.0041(7) -0.0074(7) O2 0.0332(9) 0.0222(8) 0.0359(9) 0.0140(7) 0.0054(7) -0.0013(7) O3 0.0239(8) 0.0187(8) 0.0323(9) 0.0078(6) 0.0066(7) -0.0031(7) C1 0.0337(16) 0.0323(16) 0.0383(16) 0.0104(12) 0.0120(12) -0.0039(12) C2 0.0242(12) 0.0178(12) 0.0307(13) 0.0032(9) 0.0076(10) -0.0006(10) C3 0.0205(12) 0.0253(13) 0.0322(13) 0.0060(10) 0.0024(10) 0.0021(10) C4 0.0266(13) 0.0193(12) 0.0239(13) 0.0026(10) 0.0028(10) -0.0014(9) C5 0.0229(11) 0.0135(11) 0.0278(12) 0.0037(9) 0.0072(9) -0.0029(9) C6 0.0217(12) 0.0202(12) 0.0306(13) 0.0062(10) 0.0013(10) 0.0004(10) C7 0.0301(13) 0.0210(12) 0.0266(13) 0.0046(10) 0.0035(11) -0.0024(10) C8 0.0180(11) 0.0164(11) 0.0276(12) 0.0034(9) 0.0061(9) -0.0027(9) C9 0.0255(12) 0.0230(13) 0.0302(13) 0.0014(10) 0.0095(10) -0.0060(10) C10 0.0267(13) 0.0373(15) 0.0267(13) 0.0039(11) 0.0070(11) 0.0014(11) C11 0.0270(13) 0.0306(14) 0.0375(15) 0.0092(11) 0.0120(11) 0.0116(12) C12 0.0289(13) 0.0169(12) 0.0381(14) 0.0047(10) 0.0157(11) 0.0000(10) C13 0.0229(11) 0.0224(12) 0.0256(12) 0.0012(9) 0.0097(9) -0.0030(9) 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 O1 119.82(9) y O2 S O3 102.91(9) y O1 S O3 108.77(9) y O2 S C5 110.68(10) y O1 S C5 109.25(10) y O3 S C5 104.10(9) y C8 O3 S 118.70(13) y C2 C1 H1A 112.2(16) ? C2 C1 H1B 112.1(17) ? H1A C1 H1B 102(2) ? C2 C1 H1C 111(2) ? H1A C1 H1C 108(3) ? H1B C1 H1C 111(3) ? C7 C2 C3 118.80(19) ? C7 C2 C1 120.8(2) ? C3 C2 C1 120.4(2) ? C4 C3 C2 121.3(2) ? C4 C3 H3 119.1(13) ? C2 C3 H3 119.6(13) ? C3 C4 C5 118.4(2) ? C3 C4 H4 119.2(14) ? C5 C4 H4 122.4(14) ? C4 C5 C6 121.63(19) ? C4 C5 S 119.23(16) ? C6 C5 S 119.14(16) ? C7 C6 C5 118.8(2) ? C7 C6 H6 118.9(13) ? C5 C6 H6 122.2(13) ? C6 C7 C2 121.1(2) ? C6 C7 H7 115.1(13) ? C2 C7 H7 123.9(13) ? C9 C8 C13 121.1(2) ? C9 C8 O3 121.04(18) ? C13 C8 O3 117.68(19) ? C8 C9 C10 118.8(2) ? C8 C9 H9 120.9(13) ? C10 C9 H9 120.4(13) ? C9 C10 C11 120.4(2) ? C9 C10 H10 119.3(13) ? C11 C10 H10 120.3(13) ? C12 C11 C10 120.2(2) ? C12 C11 H11 121.3(14) ? C10 C11 H11 118.5(14) ? C11 C12 C13 119.7(2) ? C11 C12 H12 121.2(14) ? C13 C12 H12 118.9(14) ? C8 C13 C12 119.7(2) ? C8 C13 Cl 120.87(17) ? C12 C13 Cl 119.38(17) ? 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 S O2 . 1.4439(16) y S O1 . 1.4460(16) y S O3 . 1.6276(16) y S C5 . 1.777(2) y Cl C13 . 1.758(2) y O3 C8 . 1.433(3) y C1 C2 . 1.524(3) y C1 H1A . 1.01(3) ? C1 H1B . 1.02(3) ? C1 H1C . 0.88(3) ? C2 C7 . 1.404(3) ? C2 C3 . 1.411(3) ? C3 C4 . 1.403(3) ? C3 H3 . 0.97(2) ? C4 C5 . 1.404(3) ? C4 H4 . 0.89(2) ? C5 C6 . 1.403(3) ? C6 C7 . 1.403(3) ? C6 H6 . 0.95(2) ? C7 H7 . 0.98(2) ? C8 C9 . 1.395(3) ? C8 C13 . 1.399(3) ? C9 C10 . 1.406(3) ? C9 H9 . 1.00(2) ? C10 C11 . 1.407(3) ? C10 H10 . 0.98(2) ? C11 C12 . 1.390(3) ? C11 H11 . 0.94(2) ? C12 C13 . 1.405(3) ? C12 H12 . 0.96(3) ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_publ_flag C1 H1B Cl 1_455 1.02(3) 3.11(3) 3.748(3) 122(2) ? C3 H3 Cl 1_455 0.97(2) 3.20(2) 4.017(3) 143.0(16) ? C3 H3 O3 1_455 0.97(2) 2.70(2) 3.613(3) 156.2(17) ? C4 H4 O1 2_565 0.89(2) 2.70(2) 3.571(3) 164.1(19) yes C6 H6 O2 2_666 0.95(2) 2.76(2) 3.477(3) 132.9(16) yes C7 H7 Cl 2_676 0.98(2) 3.30(2) 3.774(2) 111.8(15) ? C9 H9 O2 2_665 1.00(2) 2.97(2) 3.591(3) 121.2(15) ? C12 H12 O1 1_565 0.96(3) 2.77(2) 3.466(3) 130.2(17) yes C12 H12 O2 1_565 0.96(3) 2.65(3) 3.592(3) 167.2(19) 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 O2 S O3 C8 -171.50(14) ? O1 S O3 C8 60.44(16) ? C5 S O3 C8 -55.94(16) y C7 C2 C3 C4 0.4(3) ? C1 C2 C3 C4 179.9(2) ? C2 C3 C4 C5 -0.4(3) ? C3 C4 C5 C6 0.1(3) ? C3 C4 C5 S -179.28(16) ? O2 S C5 C6 22.0(2) ? O1 S C5 C6 155.95(17) ? O3 S C5 C6 -87.96(18) ? O2 S C5 C4 -158.63(17) ? O1 S C5 C4 -24.7(2) ? O3 S C5 C4 91.41(18) ? C4 C5 C6 C7 0.2(3) ? S C5 C6 C7 179.55(17) ? C5 C6 C7 C2 -0.2(3) ? C3 C2 C7 C6 -0.1(3) ? C1 C2 C7 C6 -179.6(2) ? S O3 C8 C13 112.90(19) ? S O3 C8 C9 -71.2(2) ? C13 C8 C9 C10 -1.1(3) ? O3 C8 C9 C10 -176.79(19) ? C8 C9 C10 C11 1.5(3) ? C9 C10 C11 C12 -0.7(4) ? C10 C11 C12 C13 -0.6(3) ? C9 C8 C13 C12 -0.2(3) ? O3 C8 C13 C12 175.67(18) ? C9 C8 C13 Cl -178.50(16) ? O3 C8 C13 Cl -2.6(3) ? C11 C12 C13 C8 1.0(3) ? C11 C12 C13 Cl 179.34(17) ? loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 ChemSpider 192189 2 PubChem 221506