#------------------------------------------------------------------------------ #$Date: 2011-09-28 17:24:46 +0300 (Wed, 28 Sep 2011) $ #$Revision: 26848 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/21/16/2211662.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_2211662 loop_ _publ_author_name 'Suchada Chantrapromma' 'Pumsak Ruanwas' 'Hoong-Kun Fun' 'P. S. Patil' _publ_section_title ; 2-(4-Hydroxystyryl)-1-methylpyridinium 4-bromobenzenesulfonate ; _journal_coeditor_code WN2084 _journal_issue 12 _journal_name_full 'Acta Crystallographica, Section E' _journal_page_first o5494 _journal_page_last o5496 _journal_volume 62 _journal_year 2006 _chemical_formula_iupac 'C14 H14 N O + , C6 H4 Br O3 S -' _chemical_formula_moiety 'C14 H14 N O + , C6 H4 Br O3 S -' _chemical_formula_sum 'C20 H18 Br N O4 S' _chemical_formula_weight 448.32 _chemical_melting_point .513E-305 _chemical_name_common ; 2-(4-Hydroxystyryl)-1-methylpyridinium 4-bromobenzenesulfonate ; _chemical_name_systematic ; 2-(4-Hydroxystyryl)-1-methylpyridinium 4-bromobenzenesulfonate ; _space_group_IT_number 4 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall 'P 2yb' _symmetry_space_group_name_H-M 'P 1 21 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL97 _cell_angle_alpha 90.00 _cell_angle_beta 95.9230(10) _cell_angle_gamma 90.00 _cell_formula_units_Z 2 _cell_length_a 6.28270(10) _cell_length_b 19.5377(3) _cell_length_c 7.50250(10) _cell_measurement_reflns_used 5107 _cell_measurement_temperature 100.00(10) _cell_measurement_theta_max 29.99 _cell_measurement_theta_min 2.08 _cell_volume 916.01(2) _computing_cell_refinement APEX2 _computing_data_collection 'APEX2 (Bruker, 2005)' _computing_data_reduction 'SAINT (Bruker, 2005)' _computing_molecular_graphics SHELXTL _computing_publication_material 'SHELXTL and PLATON (Spek, 2003)' _computing_structure_refinement SHELXTL _computing_structure_solution 'SHELXTL (Sheldrick, 1998)' _diffrn_ambient_temperature 297(2) _diffrn_detector_area_resol_mean 8.33 _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 1.000 _diffrn_measurement_device_type 'Bruker SMART APEXII CCD area-detector' _diffrn_measurement_method \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 0.0249 _diffrn_reflns_av_sigmaI/netI 0.0401 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_k_max 27 _diffrn_reflns_limit_k_min -27 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_number 15947 _diffrn_reflns_theta_full 29.99 _diffrn_reflns_theta_max 29.99 _diffrn_reflns_theta_min 2.08 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 2.385 _exptl_absorpt_correction_T_max 0.5223 _exptl_absorpt_correction_T_min 0.3940 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SADABS; Bruker, 2005)' _exptl_crystal_colour Purple _exptl_crystal_density_diffrn 1.625 _exptl_crystal_density_method 'not measured' _exptl_crystal_description Block _exptl_crystal_F_000 456 _exptl_crystal_size_max 0.48 _exptl_crystal_size_mid 0.39 _exptl_crystal_size_min 0.31 _refine_diff_density_max 0.603 _refine_diff_density_min -0.427 _refine_ls_abs_structure_details 'Flack (1983), with 2427 Friedel pairs' _refine_ls_abs_structure_Flack 0.013(4) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.065 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 249 _refine_ls_number_reflns 5286 _refine_ls_number_restraints 1 _refine_ls_restrained_S_all 1.065 _refine_ls_R_factor_all 0.0248 _refine_ls_R_factor_gt 0.0236 _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^)+(0.024P)^2^+0.0214P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0573 _refine_ls_wR_factor_ref 0.0576 _reflns_number_gt 5107 _reflns_number_total 5286 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file wn2084.cif _[local]_cod_cif_authors_sg_H-M 'P 21' _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. Automatic conversion script Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius ; _cod_database_code 2211662 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' loop_ _atom_site_type_symbol _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 Br Br1 -0.35458(2) 0.542441(10) 0.88108(2) 0.02165(5) Uani d . 1 S S1 0.21574(6) 0.63716(2) 0.25977(6) 0.01564(8) Uani d . 1 N N1 1.6968(2) 0.80144(7) 0.9335(2) 0.0175(3) Uani d . 1 O O1 0.3676(2) 0.68651(6) 0.34852(19) 0.0234(3) Uani d . 1 O O2 0.3201(2) 0.57579(7) 0.20216(18) 0.0217(3) Uani d . 1 O O3 0.0701(2) 0.66804(7) 0.11896(19) 0.0223(3) Uani d . 1 O O4 0.4342(2) 0.81972(7) 0.28717(19) 0.0209(3) Uani d . 1 H H1O4 0.405(4) 0.7851(15) 0.298(4) 0.029(7) Uiso d . 1 C C1 -0.1844(3) 0.56807(9) 0.6963(2) 0.0175(3) Uani d . 1 C C2 -0.2764(3) 0.56796(9) 0.5205(2) 0.0184(3) Uani d . 1 H H2A -0.4171 0.5536 0.4926 0.022 Uiso calc R 1 C C3 -0.1547(3) 0.58972(9) 0.3859(2) 0.0166(3) Uani d . 1 H H3A -0.2141 0.5903 0.2671 0.020 Uiso calc R 1 C C4 0.0568(3) 0.61062(8) 0.4299(2) 0.0154(3) Uani d . 1 C C5 0.1465(3) 0.60958(9) 0.6078(2) 0.0178(3) Uani d . 1 H H5A 0.2878 0.6231 0.6361 0.021 Uiso calc R 1 C C6 0.0262(3) 0.58846(9) 0.7433(2) 0.0189(3) Uani d . 1 H H6A 0.0849 0.5880 0.8623 0.023 Uiso calc R 1 C C7 1.8901(3) 0.81452(10) 1.0241(2) 0.0192(3) Uani d . 1 H H7A 1.9699 0.7785 1.0771 0.023 Uiso calc R 1 C C8 1.9713(3) 0.87979(10) 1.0397(2) 0.0198(3) Uani d . 1 H H8A 2.1038 0.8882 1.1031 0.024 Uiso calc R 1 C C9 1.8506(3) 0.93288(9) 0.9583(3) 0.0196(3) Uani d . 1 H H9A 1.9024 0.9775 0.9656 0.024 Uiso calc R 1 C C10 1.6532(3) 0.91912(9) 0.8664(2) 0.0181(3) Uani d . 1 H H10A 1.5725 0.9549 0.8128 0.022 Uiso calc R 1 C C11 1.5726(3) 0.85258(9) 0.8525(2) 0.0167(3) Uani d . 1 C C12 1.3673(3) 0.83454(9) 0.7565(3) 0.0197(3) Uani d . 1 H H12 1.3236 0.7892 0.7610 0.024 Uiso calc R 1 C C13 1.2360(3) 0.87866(9) 0.6615(2) 0.0183(3) Uani d . 1 H H13A 1.2800 0.9241 0.6580 0.022 Uiso calc R 1 C C14 1.0309(3) 0.86125(9) 0.5639(2) 0.0164(3) Uani d . 1 C C15 0.9595(3) 0.79371(9) 0.5400(3) 0.0193(3) Uani d . 1 H H15A 1.0471 0.7581 0.5855 0.023 Uiso calc R 1 C C16 0.7613(3) 0.77873(9) 0.4500(3) 0.0194(3) Uani d . 1 H H16A 0.7166 0.7335 0.4367 0.023 Uiso calc R 1 C C17 0.6283(3) 0.83165(9) 0.3792(2) 0.0169(3) Uani d . 1 C C18 0.6970(3) 0.89946(9) 0.4000(2) 0.0180(3) Uani d . 1 H H18A 0.6094 0.9350 0.3540 0.022 Uiso calc R 1 C C19 0.8956(3) 0.91351(9) 0.4894(2) 0.0181(3) Uani d . 1 H H19A 0.9412 0.9587 0.5005 0.022 Uiso calc R 1 C C20 1.6250(3) 0.72959(10) 0.9224(3) 0.0246(4) Uani d . 1 H H20A 1.7329 0.7008 0.9835 0.037 Uiso calc R 1 H H20B 1.6009 0.7161 0.7989 0.037 Uiso calc R 1 H H20C 1.4944 0.7251 0.9775 0.037 Uiso calc R 1 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 Br1 0.02040(8) 0.02600(8) 0.01847(8) -0.00373(7) 0.00163(5) 0.00159(8) S1 0.01578(17) 0.01394(16) 0.01682(19) -0.00035(14) -0.00011(14) 0.00063(14) N1 0.0167(6) 0.0156(7) 0.0198(7) 0.0013(5) 0.0009(5) 0.0015(5) O1 0.0242(7) 0.0198(6) 0.0254(7) -0.0075(5) -0.0016(5) 0.0013(5) O2 0.0214(6) 0.0205(6) 0.0235(7) 0.0033(5) 0.0042(5) 0.0006(5) O3 0.0220(6) 0.0232(6) 0.0212(7) 0.0032(5) -0.0011(5) 0.0045(5) O4 0.0163(6) 0.0207(7) 0.0244(7) -0.0017(5) -0.0033(5) 0.0015(5) C1 0.0204(8) 0.0148(7) 0.0177(8) 0.0002(6) 0.0033(6) 0.0008(6) C2 0.0147(7) 0.0179(7) 0.0221(9) 0.0012(6) -0.0005(6) -0.0009(6) C3 0.0169(7) 0.0173(7) 0.0147(8) 0.0013(6) -0.0021(6) 0.0000(6) C4 0.0161(7) 0.0130(6) 0.0169(8) 0.0007(6) 0.0010(6) -0.0016(6) C5 0.0149(8) 0.0177(7) 0.0199(9) -0.0017(6) -0.0023(6) -0.0015(6) C6 0.0205(8) 0.0190(7) 0.0164(8) -0.0003(6) -0.0021(6) -0.0011(6) C7 0.0166(8) 0.0238(8) 0.0170(8) 0.0026(6) 0.0007(6) 0.0021(6) C8 0.0170(8) 0.0260(8) 0.0162(8) -0.0004(6) 0.0011(6) -0.0022(6) C9 0.0177(8) 0.0186(8) 0.0220(9) -0.0014(6) 0.0001(6) -0.0013(6) C10 0.0170(8) 0.0168(7) 0.0204(9) 0.0007(6) 0.0014(6) 0.0005(6) C11 0.0141(7) 0.0185(8) 0.0179(8) 0.0025(6) 0.0031(6) 0.0005(6) C12 0.0169(8) 0.0169(7) 0.0247(9) 0.0000(6) -0.0007(7) 0.0003(7) C13 0.0163(7) 0.0166(7) 0.0216(9) -0.0013(6) 0.0006(6) -0.0011(6) C14 0.0139(7) 0.0188(7) 0.0164(8) 0.0001(6) 0.0015(6) 0.0001(6) C15 0.0166(8) 0.0156(7) 0.0255(10) 0.0031(6) 0.0004(6) 0.0006(7) C16 0.0186(8) 0.0146(7) 0.0246(9) -0.0008(6) 0.0003(7) -0.0008(6) C17 0.0157(8) 0.0182(8) 0.0168(8) -0.0009(6) 0.0026(6) 0.0005(6) C18 0.0192(7) 0.0164(7) 0.0181(8) 0.0020(6) 0.0002(6) 0.0013(6) C19 0.0185(8) 0.0147(7) 0.0211(9) 0.0011(6) 0.0015(6) 0.0009(6) C20 0.0228(9) 0.0165(8) 0.0334(10) -0.0003(7) -0.0023(7) 0.0039(7) 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' Br Br -0.2901 2.4595 '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 O2 S1 O3 113.28(8) O2 S1 O1 112.64(8) O3 S1 O1 112.81(8) O2 S1 C4 106.08(8) O3 S1 C4 106.54(8) O1 S1 C4 104.66(8) C7 N1 C11 121.68(15) C7 N1 C20 117.49(15) C11 N1 C20 120.82(15) C17 O4 H1O4 109(2) C2 C1 C6 122.33(16) C2 C1 Br1 118.88(13) C6 C1 Br1 118.76(14) C1 C2 C3 118.88(16) C1 C2 H2A 120.6 C3 C2 H2A 120.6 C2 C3 C4 119.84(16) C2 C3 H3A 120.1 C4 C3 H3A 120.1 C5 C4 C3 120.16(16) C5 C4 S1 119.37(13) C3 C4 S1 120.46(13) C6 C5 C4 120.53(16) C6 C5 H5A 119.7 C4 C5 H5A 119.7 C5 C6 C1 118.26(17) C5 C6 H6A 120.9 C1 C6 H6A 120.9 N1 C7 C8 121.61(17) N1 C7 H7A 119.2 C8 C7 H7A 119.2 C7 C8 C9 118.32(17) C7 C8 H8A 120.8 C9 C8 H8A 120.8 C10 C9 C8 119.71(17) C10 C9 H9A 120.1 C8 C9 H9A 120.1 C9 C10 C11 121.22(17) C9 C10 H10A 119.4 C11 C10 H10A 119.4 N1 C11 C10 117.45(16) N1 C11 C12 118.56(15) C10 C11 C12 123.98(16) C13 C12 C11 124.82(16) C13 C12 H12 117.6 C11 C12 H12 117.6 C12 C13 C14 125.41(16) C12 C13 H13A 117.3 C14 C13 H13A 117.3 C15 C14 C19 117.44(16) C15 C14 C13 122.71(16) C19 C14 C13 119.85(15) C16 C15 C14 121.46(16) C16 C15 H15A 119.3 C14 C15 H15A 119.3 C15 C16 C17 120.03(16) C15 C16 H16A 120.0 C17 C16 H16A 120.0 O4 C17 C18 118.07(16) O4 C17 C16 122.40(16) C18 C17 C16 119.53(16) C19 C18 C17 119.72(16) C19 C18 H18A 120.1 C17 C18 H18A 120.1 C18 C19 C14 121.80(16) C18 C19 H19A 119.1 C14 C19 H19A 119.1 N1 C20 H20A 109.5 N1 C20 H20B 109.5 H20A C20 H20B 109.5 N1 C20 H20C 109.5 H20A C20 H20C 109.5 H20B C20 H20C 109.5 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag Br1 C1 1.9034(17) y S1 O2 1.4535(13) y S1 O3 1.4551(14) y S1 O1 1.4671(13) y S1 C4 1.7771(18) y N1 C7 1.354(2) ? N1 C11 1.370(2) ? N1 C20 1.474(2) y O4 C17 1.358(2) y O4 H1O4 0.71(3) ? C1 C2 1.384(3) ? C1 C6 1.392(3) ? C2 C3 1.394(2) ? C2 H2A 0.9300 ? C3 C4 1.397(2) ? C3 H3A 0.9300 ? C4 C5 1.394(2) ? C5 C6 1.391(3) ? C5 H5A 0.9300 ? C6 H6A 0.9300 ? C7 C8 1.374(3) ? C7 H7A 0.9300 ? C8 C9 1.389(3) ? C8 H8A 0.9300 ? C9 C10 1.382(2) ? C9 H9A 0.9300 ? C10 C11 1.395(2) ? C10 H10A 0.9300 ? C11 C12 1.455(2) ? C12 C13 1.345(2) y C12 H12 0.9300 ? C13 C14 1.456(2) ? C13 H13A 0.9300 ? C14 C15 1.399(2) ? C14 C19 1.407(2) ? C15 C16 1.385(3) ? C15 H15A 0.9300 ? C16 C17 1.399(2) ? C16 H16A 0.9300 ? C17 C18 1.397(2) ? C18 C19 1.382(2) ? C18 H18A 0.9300 ? C19 H19A 0.9300 ? C20 H20A 0.9600 ? C20 H20B 0.9600 ? C20 H20C 0.9600 ? 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 O4 H1O4 O1 1_555 0.71(3) 1.98(3) 2.6833(18) 171(3) y C5 H5A O1 1_555 0.93 2.5816 2.921(2) 102 y C6 H6A O3 1_556 0.93 2.4898 3.206(2) 134 y C7 H7A O3 1_756 0.93 2.2609 3.132(2) 156 y C10 H10A O2 2_756 0.93 2.4621 3.111(2) 127 y C16 H16A O1 1_555 0.93 2.4060 3.091(2) 130 y C20 H20A O3 1_756 0.96 2.3423 3.254(2) 158 y C16 H16A Cg1 1_655 0.93 3.2400 3.9330(19) 133 y C19 H19A Cg1 2_656 0.93 2.7198 3.6245(19) 165 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 C6 C1 C2 C3 -0.7(3) ? Br1 C1 C2 C3 177.11(12) ? C1 C2 C3 C4 0.5(2) ? C2 C3 C4 C5 0.2(2) ? C2 C3 C4 S1 178.96(13) ? O2 S1 C4 C5 89.10(15) ? O3 S1 C4 C5 -149.93(14) ? O1 S1 C4 C5 -30.21(16) ? O2 S1 C4 C3 -89.68(14) ? O3 S1 C4 C3 31.29(15) ? O1 S1 C4 C3 151.01(13) ? C3 C4 C5 C6 -0.7(2) ? S1 C4 C5 C6 -179.44(13) ? C4 C5 C6 C1 0.5(3) ? C2 C1 C6 C5 0.2(3) ? Br1 C1 C6 C5 -177.57(13) ? C11 N1 C7 C8 0.1(3) ? C20 N1 C7 C8 179.22(17) y N1 C7 C8 C9 -0.6(3) ? C7 C8 C9 C10 0.7(3) ? C8 C9 C10 C11 -0.4(3) ? C7 N1 C11 C10 0.1(3) ? C20 N1 C11 C10 -178.91(16) ? C7 N1 C11 C12 179.58(16) ? C20 N1 C11 C12 0.5(2) ? C9 C10 C11 N1 0.0(3) ? C9 C10 C11 C12 -179.40(16) ? N1 C11 C12 C13 -175.52(17) ? C10 C11 C12 C13 3.9(3) ? C11 C12 C13 C14 179.58(17) y C12 C13 C14 C15 -8.3(3) ? C12 C13 C14 C19 171.64(18) ? C19 C14 C15 C16 -1.5(3) ? C13 C14 C15 C16 178.47(17) ? C14 C15 C16 C17 0.6(3) ? C15 C16 C17 O4 178.80(16) ? C15 C16 C17 C18 0.0(3) ? O4 C17 C18 C19 -178.53(15) ? C16 C17 C18 C19 0.3(3) ? C17 C18 C19 C14 -1.3(3) ? C15 C14 C19 C18 1.8(3) ? C13 C14 C19 C18 -178.13(16) ?