#------------------------------------------------------------------------------ #$Date: 2025-08-19 11:43:10 +0100 (Tue, 19 Aug 2025) $ #$Revision: 301803 $ #$URL: svn://www.crystallography.net/cod/cif/2/20/21/2202138.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_2202138 loop_ _publ_author_name 'Nagarajan Vembu' 'Maruthai Nallu' 'Jered Garrison' 'Khadijah Hindi' 'Wiley J. Youngs' _publ_section_title ; 4-Methoxyphenyl 4-toluenesulfonate: supramolecular aggregation through C---H···O and C---H···\p interactions ; _journal_issue 6 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o830 _journal_page_last o832 _journal_paper_doi 10.1107/S1600536803010444 _journal_volume 59 _journal_year 2003 _chemical_formula_iupac 'C14 H14 O4 S' _chemical_formula_moiety 'C14 H14 O4 S' _chemical_formula_sum 'C14 H14 O4 S' _chemical_formula_weight 278.31 _chemical_melting_point .72E-71 _chemical_name_common '4-methoxylphenyl p-toluenesulfonate' _chemical_name_systematic ; 4-Methoxyphenyl 4-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' _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 108.049(5) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 14.778(5) _cell_length_b 5.6665(18) _cell_length_c 16.133(5) _cell_measurement_reflns_used 5896 _cell_measurement_temperature 100(2) _cell_measurement_theta_max 27.62 _cell_measurement_theta_min 2.60 _cell_volume 1284.5(7) _computing_cell_refinement SMART _computing_data_collection 'SMART (Bruker, 1998)' _computing_data_reduction 'SAINT (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_measured_fraction_theta_full 0.984 _diffrn_measured_fraction_theta_max 0.984 _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 0.0416 _diffrn_reflns_av_sigmaI/netI 0.0405 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_number 10615 _diffrn_reflns_theta_full 27.66 _diffrn_reflns_theta_max 27.66 _diffrn_reflns_theta_min 1.45 _diffrn_standards_decay_% 0 _exptl_absorpt_coefficient_mu 0.259 _exptl_absorpt_correction_T_max 0.974 _exptl_absorpt_correction_T_min 0.736 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SADABS; Sheldrick, 1996)' _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.439 _exptl_crystal_density_method 'not measured' _exptl_crystal_description plate _exptl_crystal_F_000 584 _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _refine_diff_density_max 0.582 _refine_diff_density_min -0.454 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.235 _refine_ls_hydrogen_treatment refall _refine_ls_matrix_type full _refine_ls_number_parameters 228 _refine_ls_number_reflns 2956 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.235 _refine_ls_R_factor_all 0.0649 _refine_ls_R_factor_gt 0.0583 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w = 1/[\s^2^(Fo^2^)+(0.0403P)^2^+1.3915P] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1252 _refine_ls_wR_factor_ref 0.1282 _reflns_number_gt 2687 _reflns_number_total 2956 _reflns_threshold_expression I>2\s(I) _cod_data_source_file ob6243.cif _cod_data_source_block I _cod_original_cell_volume 1284.6(7) _cod_original_sg_symbol_H-M 'P 21/c' _cod_database_code 2202138 _cod_database_fobs_code 2202138 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_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 0.29343(4) 0.31557(10) 1.01208(3) 0.01666(16) Uani d . 1 . . S O1 0.36007(12) 0.3968(3) 0.97108(10) 0.0222(4) Uani d . 1 . . O O2 0.27097(13) 0.0713(3) 1.00823(11) 0.0255(4) Uani d . 1 . . O O3 0.19711(11) 0.4602(3) 0.97292(10) 0.0186(4) Uani d . 1 . . O O4 0.06857(12) 0.5138(3) 0.61427(10) 0.0204(4) Uani d . 1 . . O C1 0.4361(2) 0.6151(5) 1.38654(16) 0.0244(5) Uani d . 1 . . C C2 0.39454(16) 0.5464(4) 1.29296(15) 0.0169(5) Uani d . 1 . . C C3 0.34358(17) 0.3382(4) 1.26940(15) 0.0186(5) Uani d . 1 . . C C4 0.30937(17) 0.2696(4) 1.18300(15) 0.0170(5) Uani d . 1 . . C C5 0.32683(16) 0.4115(4) 1.12017(14) 0.0160(4) Uani d . 1 . . C C6 0.37595(17) 0.6218(4) 1.14139(15) 0.0186(5) Uani d . 1 . . C C7 0.40901(17) 0.6875(4) 1.22803(15) 0.0189(5) Uani d . 1 . . C C8 0.16490(16) 0.4770(4) 0.88075(14) 0.0158(5) Uani d . 1 . . C C9 0.10953(16) 0.2981(4) 0.83259(15) 0.0171(5) Uani d . 1 . . C C10 0.07859(17) 0.3181(4) 0.74319(15) 0.0170(5) Uani d . 1 . . C C11 0.10301(16) 0.5126(4) 0.70274(14) 0.0160(5) Uani d . 1 . . C C12 0.15840(17) 0.6912(4) 0.75221(15) 0.0181(5) Uani d . 1 . . C C13 0.18938(17) 0.6716(4) 0.84253(15) 0.0186(5) Uani d . 1 . . C C14 0.0923(2) 0.7116(5) 0.56985(16) 0.0257(6) Uani d . 1 . . C H1A 0.438(3) 0.775(8) 1.396(3) 0.064(12) Uiso d . 1 . . H H1B 0.502(3) 0.586(7) 1.404(2) 0.060(11) Uiso d . 1 . . H H1C 0.407(3) 0.538(7) 1.423(3) 0.065(12) Uiso d . 1 . . H H3 0.332(2) 0.249(5) 1.311(2) 0.028(8) Uiso d . 1 . . H H4 0.2766(19) 0.126(5) 1.1668(17) 0.020(7) Uiso d . 1 . . H H6 0.3870(18) 0.717(5) 1.0984(18) 0.018(7) Uiso d . 1 . . H H7 0.4447(19) 0.829(5) 1.2449(18) 0.020(7) Uiso d . 1 . . H H9 0.0927(19) 0.165(5) 0.8590(18) 0.020(7) Uiso d . 1 . . H H10 0.042(2) 0.207(5) 0.7107(19) 0.025(7) Uiso d . 1 . . H H12 0.1737(19) 0.819(5) 0.7264(17) 0.017(7) Uiso d . 1 . . H H13 0.2274(19) 0.788(5) 0.8764(18) 0.019(7) Uiso d . 1 . . H H14A 0.160(2) 0.720(5) 0.5829(19) 0.025(7) Uiso d . 1 . . H H14B 0.060(2) 0.680(5) 0.508(2) 0.028(8) Uiso d . 1 . . H H14C 0.065(2) 0.857(5) 0.5862(18) 0.025(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 0.0244(3) 0.0148(3) 0.0106(3) 0.0031(2) 0.0051(2) -0.0009(2) O1 0.0254(9) 0.0279(9) 0.0149(8) 0.0048(7) 0.0087(7) 0.0016(7) O2 0.0412(11) 0.0161(9) 0.0177(9) 0.0022(8) 0.0068(8) -0.0025(7) O3 0.0237(9) 0.0209(8) 0.0111(8) 0.0037(7) 0.0053(6) -0.0012(6) O4 0.0282(9) 0.0206(9) 0.0113(8) -0.0039(7) 0.0048(7) 0.0006(6) C1 0.0309(14) 0.0265(14) 0.0152(12) -0.0039(11) 0.0064(10) -0.0049(10) C2 0.0182(11) 0.0172(11) 0.0154(11) 0.0028(9) 0.0057(9) -0.0019(9) C3 0.0239(12) 0.0194(12) 0.0146(11) -0.0006(9) 0.0092(9) 0.0030(9) C4 0.0225(12) 0.0134(11) 0.0160(11) -0.0024(9) 0.0075(9) -0.0001(9) C5 0.0208(11) 0.0146(11) 0.0119(10) 0.0021(9) 0.0040(8) -0.0011(8) C6 0.0259(12) 0.0147(11) 0.0166(11) 0.0011(9) 0.0083(9) 0.0042(9) C7 0.0238(12) 0.0135(11) 0.0195(11) -0.0020(9) 0.0069(9) -0.0038(9) C8 0.0200(11) 0.0167(11) 0.0100(10) 0.0047(9) 0.0036(8) -0.0011(8) C9 0.0211(11) 0.0146(11) 0.0174(11) -0.0005(9) 0.0083(9) 0.0018(9) C10 0.0202(11) 0.0129(11) 0.0181(11) -0.0001(9) 0.0064(9) -0.0038(9) C11 0.0177(11) 0.0166(11) 0.0139(10) 0.0031(9) 0.0050(8) 0.0000(9) C12 0.0217(12) 0.0133(11) 0.0191(11) -0.0017(9) 0.0059(9) 0.0008(9) C13 0.0227(12) 0.0133(11) 0.0186(11) -0.0001(9) 0.0045(9) -0.0042(9) C14 0.0363(15) 0.0242(14) 0.0158(12) -0.0039(11) 0.0068(10) 0.0043(10) 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_publ_flag O2 S O1 118.77(11) y O2 S O3 108.41(11) y O1 S O3 108.13(10) y O2 S C5 109.71(11) y O1 S C5 109.97(11) y O3 S C5 100.21(10) y C8 O3 S 114.78(13) y C11 O4 C14 117.35(18) y C2 C1 H1A 114(3) ? C2 C1 H1B 109(2) ? H1A C1 H1B 98(3) ? C2 C1 H1C 113(3) ? H1A C1 H1C 110(4) ? H1B C1 H1C 111(3) ? C7 C2 C3 118.7(2) ? C7 C2 C1 120.1(2) ? C3 C2 C1 121.1(2) ? C4 C3 C2 120.9(2) ? C4 C3 H3 120(2) ? C2 C3 H3 119.0(19) ? C5 C4 C3 118.9(2) ? C5 C4 H4 119.9(16) ? C3 C4 H4 121.2(16) ? C4 C5 C6 121.6(2) ? C4 C5 S 119.54(18) ? C6 C5 S 118.71(17) ? C7 C6 C5 118.5(2) ? C7 C6 H6 120.7(17) ? C5 C6 H6 120.9(17) ? C6 C7 C2 121.4(2) ? C6 C7 H7 120.5(17) ? C2 C7 H7 118.1(17) ? C13 C8 C9 122.2(2) ? C13 C8 O3 118.6(2) ? C9 C8 O3 119.3(2) ? C10 C9 C8 118.4(2) ? C10 C9 H9 119.7(17) ? C8 C9 H9 121.9(16) ? C9 C10 C11 120.6(2) ? C9 C10 H10 120.3(19) ? C11 C10 H10 119.1(19) ? O4 C11 C10 115.6(2) ? O4 C11 C12 124.3(2) ? C10 C11 C12 120.2(2) ? C11 C12 C13 119.3(2) ? C11 C12 H12 120.6(17) ? C13 C12 H12 120.2(17) ? C8 C13 C12 119.4(2) ? C8 C13 H13 120.3(17) ? C12 C13 H13 120.3(17) ? O4 C14 H14A 109.3(18) ? O4 C14 H14B 104.7(17) ? H14A C14 H14B 112(2) ? O4 C14 H14C 109.7(17) ? H14A C14 H14C 112(2) ? H14B C14 H14C 109(2) ? 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 . 1.4200(19) y S O1 . 1.4223(18) y S O3 . 1.5936(17) y S C5 . 1.745(2) y O3 C8 . 1.417(3) y O4 C11 . 1.359(3) y O4 C14 . 1.432(3) y C1 C2 . 1.495(3) y C1 H1A . 0.92(5) ? C1 H1B . 0.95(4) ? C1 H1C . 0.94(4) ? C2 C7 . 1.386(3) ? C2 C3 . 1.388(3) ? C3 C4 . 1.383(3) ? C3 H3 . 0.90(3) ? C4 C5 . 1.380(3) ? C4 H4 . 0.94(3) ? C5 C6 . 1.382(3) ? C6 C7 . 1.381(3) ? C6 H6 . 0.93(3) ? C7 H7 . 0.95(3) ? C8 C13 . 1.366(3) ? C8 C9 . 1.381(3) ? C9 C10 . 1.376(3) ? C9 H9 . 0.94(3) ? C10 C11 . 1.385(3) ? C10 H10 . 0.89(3) ? C11 C12 . 1.388(3) ? C12 C13 . 1.390(3) ? C12 H12 . 0.90(3) ? C13 H13 . 0.93(3) ? C14 H14A . 0.96(3) ? C14 H14B . 0.99(3) ? C14 H14C . 0.98(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 H1A O1 4_576 0.92(5) 2.67(4) 3.424(3) 141(3) y C1 H1B O1 2_657 0.95(4) 2.96(4) 3.551(3) 122(3) y C1 H1C O1 4_566 0.94(4) 2.73(4) 3.534(4) 143(3) y C1 H1C O2 4_566 0.94(4) 2.83(4) 3.728(3) 160(3) y C3 H3 O1 4_566 0.90(3) 2.61(3) 3.454(3) 155(2) y C6 H6 O2 1_565 0.93(3) 2.75(3) 3.383(3) 126(2) y C9 H9 O4 2_546 0.94(3) 2.69(3) 3.414(3) 135(2) y C13 H13 O2 1_565 0.93(3) 2.58(3) 3.426(3) 152(2) y C14 H14A O2 4_565 0.96(3) 2.84(3) 3.486(4) 125(2) y C14 H14A O3 4_575 0.96(3) 2.71(3) 3.131(3) 107(2) y C14 H14B O4 3_566 0.99(3) 2.53(3) 3.425(3) 152(2) y C3 H3 Cg2 4_586 0.90(3) 3.17 3.742 124 y C7 H7 Cg1 2_646 0.95(3) 2.88 3.644 138 y C10 H10 Cg2 2_555 0.89(3) 2.85 3.527 134 y C12 H12 Cg1 4_575 0.90(3) 3.09 3.781 135 y 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 -82.6(2) ? O1 S O3 C8 47.4(2) ? C5 S O3 C8 162.5(2) y C7 C2 C3 C4 1.3(4) ? C1 C2 C3 C4 -176.7(2) ? C2 C3 C4 C5 0.1(4) ? C3 C4 C5 C6 -1.2(4) ? C3 C4 C5 S 174.4(2) ? O2 S C5 C4 -13.4(2) ? O1 S C5 C4 -145.8(2) ? O3 S C5 C4 100.5(2) ? O2 S C5 C6 162.4(2) ? O1 S C5 C6 30.0(2) ? O3 S C5 C6 -83.7(2) ? C4 C5 C6 C7 0.9(4) ? S C5 C6 C7 -174.8(2) ? C5 C6 C7 C2 0.6(4) ? C3 C2 C7 C6 -1.7(4) ? C1 C2 C7 C6 176.4(2) ? S O3 C8 C13 -94.7(2) ? S O3 C8 C9 85.8(2) ? C13 C8 C9 C10 0.2(3) ? O3 C8 C9 C10 179.7(2) ? C8 C9 C10 C11 0.4(3) ? C14 O4 C11 C10 -179.9(2) ? C14 O4 C11 C12 0.8(3) ? C9 C10 C11 O4 180.0(2) ? C9 C10 C11 C12 -0.6(3) ? O4 C11 C12 C13 179.7(2) ? C10 C11 C12 C13 0.4(3) ? C9 C8 C13 C12 -0.4(4) ? O3 C8 C13 C12 -180.0(2) ? C11 C12 C13 C8 0.1(3) ? loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 ChemSpider 9634959 2 PubChem 11460118