#------------------------------------------------------------------------------ #$Date: 2025-08-19 11:43:10 +0100 (Tue, 19 Aug 2025) $ #$Revision: 301803 $ #$URL: svn://www.crystallography.net/cod/cif/2/20/67/2206742.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_2206742 loop_ _publ_author_name 'Rodr\'iguez, Ricaurte' 'Nogueras, Manuel' 'Cobo, Justo' 'Low, John N.' 'Glidewell, Christopher' _publ_section_title ; 1-(4-Methylphenylsulfonyl)-1H-1,2,3-benzotriazole: sheets built from C---H···N, C---H···O and C---H···\p(arene) hydrogen bonds ; _journal_coeditor_code LH6480 _journal_issue 9 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o2795 _journal_page_last o2797 _journal_paper_doi 10.1107/S1600536805024219 _journal_volume 61 _journal_year 2005 _chemical_formula_iupac 'C13 H11 N3 O2 S' _chemical_formula_moiety 'C13 H11 N3 O2 S' _chemical_formula_sum 'C13 H11 N3 O2 S' _chemical_formula_weight 273.31 _chemical_name_systematic ; 1-(4-Methylphenylsulfonyl)-1H-1,2,3-benzotriazole ; _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 _cell_angle_alpha 98.614(3) _cell_angle_beta 104.249(2) _cell_angle_gamma 102.684(3) _cell_formula_units_Z 2 _cell_length_a 7.4211(3) _cell_length_b 9.2176(3) _cell_length_c 9.7823(3) _cell_measurement_reflns_used 2825 _cell_measurement_temperature 120(2) _cell_measurement_theta_max 27.49 _cell_measurement_theta_min 4.07 _cell_volume 617.87(4) _computing_cell_refinement 'DENZO (Otwinowski & Minor, 1997) and COLLECT' _computing_data_collection 'COLLECT (Hooft, 1999)' _computing_data_reduction 'DENZO and COLLECT' _computing_molecular_graphics 'PLATON (Spek, 2003)' _computing_publication_material 'SHELXL 97 and PRPKAPPA (Ferguson, 1999)' _computing_structure_refinement 'OSCAIL and SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'OSCAIL (McArdle, 2003) and SHELXS97 (Sheldrick, 1997)' _diffrn_ambient_temperature 120(2) _diffrn_detector_area_resol_mean 9.091 _diffrn_measured_fraction_theta_full 0.996 _diffrn_measured_fraction_theta_max 0.996 _diffrn_measurement_device_type 'Bruker--Nonius 95mm CCD camera on \k goniostat' _diffrn_measurement_method '\f and \w' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'Bruker--Nonius FR91 rotating anode' _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0361 _diffrn_reflns_av_sigmaI/netI 0.0284 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_number 14360 _diffrn_reflns_theta_full 27.49 _diffrn_reflns_theta_max 27.49 _diffrn_reflns_theta_min 4.07 _diffrn_standards_decay_% nil _exptl_absorpt_coefficient_mu 0.263 _exptl_absorpt_correction_T_max 0.967 _exptl_absorpt_correction_T_min 0.931 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SADABS; Sheldrick, 2003)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.469 _exptl_crystal_density_method 'not measured' _exptl_crystal_description needle _exptl_crystal_F_000 284 _exptl_crystal_size_max 0.42 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.13 _refine_diff_density_max 0.314 _refine_diff_density_min -0.482 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.052 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 173 _refine_ls_number_reflns 2825 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.052 _refine_ls_R_factor_all 0.0470 _refine_ls_R_factor_gt 0.0371 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^)+(0.0482P)^2^+0.2971P] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0912 _refine_ls_wR_factor_ref 0.0976 _reflns_number_gt 2398 _reflns_number_total 2825 _reflns_threshold_expression I>2\s(I) _cod_data_source_file lh6480.cif _cod_data_source_block I _cod_database_code 2206742 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_type_symbol S1 0.11158(5) 0.24195(4) 0.27755(4) 0.01978(12) Uani d . 1 S O1 -0.04859(16) 0.12509(12) 0.18262(12) 0.0239(3) Uani d . 1 O O2 0.09049(17) 0.38368(12) 0.34172(13) 0.0271(3) Uani d . 1 O N1 0.19364(18) 0.16134(14) 0.41598(13) 0.0192(3) Uani d . 1 N N2 0.30931(19) 0.25264(15) 0.54843(14) 0.0233(3) Uani d . 1 N N3 0.36838(19) 0.16548(15) 0.63068(14) 0.0237(3) Uani d . 1 N C3A 0.2980(2) 0.01522(18) 0.55519(16) 0.0203(3) Uani d . 1 C C4 0.3228(2) -0.11862(19) 0.59964(17) 0.0243(3) Uani d . 1 C C5 0.2353(2) -0.25318(19) 0.49941(18) 0.0255(3) Uani d . 1 C C6 0.1253(2) -0.25627(18) 0.35900(18) 0.0245(3) Uani d . 1 C C7 0.0970(2) -0.12581(17) 0.31394(17) 0.0219(3) Uani d . 1 C C7A 0.1871(2) 0.01037(16) 0.41622(16) 0.0181(3) Uani d . 1 C C11 0.2978(2) 0.27397(17) 0.19644(16) 0.0195(3) Uani d . 1 C C12 0.2910(2) 0.16746(19) 0.07693(17) 0.0247(3) Uani d . 1 C C13 0.4358(3) 0.1974(2) 0.01053(17) 0.0283(4) Uani d . 1 C C14 0.5868(2) 0.3303(2) 0.06199(17) 0.0262(4) Uani d . 1 C C15 0.5907(2) 0.43337(19) 0.18311(18) 0.0270(4) Uani d . 1 C C16 0.4467(2) 0.40703(17) 0.25090(17) 0.0233(3) Uani d . 1 C C141 0.7412(3) 0.3617(2) -0.0133(2) 0.0364(4) Uani d . 1 C H4 0.3968 -0.1164 0.6946 0.029 Uiso calc R 1 H H5 0.2493 -0.3462 0.5256 0.031 Uiso calc R 1 H H6 0.0685 -0.3516 0.2927 0.029 Uiso calc R 1 H H7 0.0211 -0.1286 0.2195 0.026 Uiso calc R 1 H H12 0.1892 0.0762 0.0417 0.030 Uiso calc R 1 H H13 0.4321 0.1260 -0.0716 0.034 Uiso calc R 1 H H14A 0.8119 0.4697 0.0173 0.055 Uiso calc R 1 H H14B 0.6814 0.3363 -0.1180 0.055 Uiso calc R 1 H H14C 0.8307 0.2995 0.0120 0.055 Uiso calc R 1 H H15 0.6941 0.5235 0.2200 0.032 Uiso calc R 1 H H16 0.4499 0.4785 0.3328 0.028 Uiso calc R 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 S1 0.0225(2) 0.0162(2) 0.0206(2) 0.00567(15) 0.00558(15) 0.00415(14) O1 0.0221(5) 0.0214(6) 0.0243(6) 0.0029(4) 0.0020(5) 0.0053(4) O2 0.0341(6) 0.0182(6) 0.0333(6) 0.0105(5) 0.0144(5) 0.0055(5) N1 0.0224(6) 0.0159(6) 0.0167(6) 0.0034(5) 0.0042(5) 0.0007(5) N2 0.0249(7) 0.0224(7) 0.0180(6) 0.0025(5) 0.0052(5) -0.0019(5) N3 0.0235(7) 0.0278(7) 0.0176(6) 0.0046(6) 0.0056(5) 0.0020(5) C3A 0.0181(7) 0.0266(8) 0.0168(7) 0.0057(6) 0.0072(6) 0.0035(6) C4 0.0226(8) 0.0338(9) 0.0217(8) 0.0115(7) 0.0087(6) 0.0121(7) C5 0.0270(8) 0.0256(8) 0.0313(9) 0.0117(7) 0.0130(7) 0.0135(7) C6 0.0258(8) 0.0187(7) 0.0291(9) 0.0057(6) 0.0091(7) 0.0043(6) C7 0.0242(8) 0.0200(8) 0.0192(7) 0.0052(6) 0.0039(6) 0.0024(6) C7A 0.0189(7) 0.0177(7) 0.0191(7) 0.0049(6) 0.0074(6) 0.0047(6) C11 0.0224(7) 0.0196(7) 0.0171(7) 0.0062(6) 0.0049(6) 0.0059(6) C12 0.0279(8) 0.0238(8) 0.0184(7) 0.0052(6) 0.0026(6) 0.0021(6) C13 0.0335(9) 0.0335(9) 0.0180(8) 0.0117(7) 0.0068(7) 0.0031(7) C14 0.0265(8) 0.0342(9) 0.0217(8) 0.0111(7) 0.0072(7) 0.0127(7) C15 0.0257(8) 0.0261(8) 0.0278(9) 0.0036(7) 0.0063(7) 0.0087(7) C16 0.0276(8) 0.0189(7) 0.0219(8) 0.0051(6) 0.0056(6) 0.0041(6) C141 0.0321(9) 0.0555(12) 0.0311(9) 0.0170(9) 0.0152(8) 0.0198(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' N N 0.0061 0.0033 '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 N2 N1 S1 119.98(10) y C7A N1 S1 129.49(11) y N2 N1 C7A 109.89(12) y O1 S1 O2 121.89(7) y O2 S1 N1 105.81(7) no O1 S1 N1 103.96(6) no O2 S1 C11 109.56(7) no O1 S1 C11 109.29(7) no N1 S1 C11 104.84(7) no C16 C11 C12 121.61(15) no C16 C11 S1 119.06(12) no C12 C11 S1 119.31(12) no C13 C12 C11 118.56(15) no C13 C12 H12 120.7 no C11 C12 H12 120.7 no C12 C13 C14 121.27(15) no C12 C13 H13 119.4 no C14 C13 H13 119.4 no C15 C14 C13 118.65(15) no C15 C14 C141 120.97(16) no C13 C14 C141 120.37(16) no C14 C141 H14A 109.5 no C14 C141 H14B 109.5 no H14A C141 H14B 109.5 no C14 C141 H14C 109.5 no H14A C141 H14C 109.5 no H14B C141 H14C 109.5 no C16 C15 C14 121.32(15) no C16 C15 H15 119.3 no C14 C15 H15 119.3 no C15 C16 C11 118.58(15) no C15 C16 H16 120.7 no C11 C16 H16 120.7 no N3 N2 N1 108.15(12) no N2 N3 C3A 109.35(13) no N3 C3A C7A 108.99(13) no N3 C3A C4 129.97(14) no C7A C3A C4 121.03(14) no C5 C4 C3A 116.89(14) no C5 C4 H4 121.6 no C3A C4 H4 121.6 no C4 C5 C6 121.48(15) no C4 C5 H5 119.3 no C6 C5 H5 119.3 no C7 C6 C5 122.44(15) no C7 C6 H6 118.8 no C5 C6 H6 118.8 no C6 C7 C7A 115.69(14) no C6 C7 H7 122.2 no C7A C7 H7 122.2 no N1 C7A C3A 103.57(13) no N1 C7A C7 133.95(14) no C3A C7A C7 122.46(14) no loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag N1 N2 1.390(2) y N2 N3 1.288(2) y N3 C3A 1.387(2) y C3A C7A 1.394(2) y C7A N1 1.3821(19) y C3A C4 1.402(2) y C4 C5 1.375(2) y C5 C6 1.407(2) y C6 C7 1.382(2) y C7 C7A 1.396(2) y N1 S1 1.6885(13) no S1 O2 1.4205(11) no S1 O1 1.4248(11) no S1 C11 1.7486(15) no C11 C16 1.389(2) no C11 C12 1.392(2) no C12 C13 1.386(2) no C12 H12 0.95 no C13 C14 1.395(2) no C13 H13 0.95 no C14 C15 1.393(2) no C14 C141 1.507(2) no C141 H14A 0.98 no C141 H14B 0.98 no C141 H14C 0.98 no C15 C16 1.387(2) no C15 H15 0.95 no C16 H16 0.95 no C4 H4 0.95 no C5 H5 0.95 no C6 H6 0.95 no C7 H7 0.95 no 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 C4 H4 Cg1 2_656 0.95 2.84 3.641(2) 143 y C6 H6 O2 1_545 0.95 2.59 3.247(2) 127 y C12 H12 O1 2_555 0.95 2.48 3.244(2) 137 y C16 H16 N2 2_666 0.95 2.62 3.299(2) 129 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 C7A N1 S1 O2 159.42(13) no N2 N1 S1 O2 -30.75(13) no C7A N1 S1 O1 29.92(15) no N2 N1 S1 O1 -160.25(11) no C7A N1 S1 C11 -84.79(14) no N2 N1 S1 C11 85.03(12) no O2 S1 C11 C16 27.59(14) no O1 S1 C11 C16 163.52(12) no N1 S1 C11 C16 -85.56(13) no O2 S1 C11 C12 -150.89(12) no O1 S1 C11 C12 -14.97(14) no N1 S1 C11 C12 95.96(13) no C16 C11 C12 C13 -0.9(2) no S1 C11 C12 C13 177.53(12) no C11 C12 C13 C14 0.5(2) no C12 C13 C14 C15 0.4(3) no C12 C13 C14 C141 -179.08(15) no C13 C14 C15 C16 -1.0(2) no C141 C14 C15 C16 178.45(15) no C14 C15 C16 C11 0.7(2) no C12 C11 C16 C15 0.3(2) no S1 C11 C16 C15 -178.13(12) no C7A N1 N2 N3 -2.03(16) no S1 N1 N2 N3 -173.70(10) no N1 N2 N3 C3A 1.29(16) no N2 N3 C3A C7A -0.12(17) no N2 N3 C3A C4 -179.63(15) no N3 C3A C4 C5 -179.67(15) no C7A C3A C4 C5 0.9(2) no C3A C4 C5 C6 -0.2(2) no C4 C5 C6 C7 -0.7(2) no C5 C6 C7 C7A 0.9(2) no N2 N1 C7A C3A 1.86(16) no S1 N1 C7A C3A 172.49(11) no N2 N1 C7A C7 -179.17(16) no S1 N1 C7A C7 -8.5(3) no N3 C3A C7A N1 -1.08(16) no C4 C3A C7A N1 178.48(13) no N3 C3A C7A C7 179.80(13) no C4 C3A C7A C7 -0.6(2) no C6 C7 C7A N1 -179.09(16) no C6 C7 C7A C3A -0.3(2) no loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 ChemSpider 1154862 2 PubChem 1380969