#------------------------------------------------------------------------------ #$Date: 2016-02-19 14:29:56 +0000 (Fri, 19 Feb 2016) $ #$Revision: 176759 $ #$URL: svn://www.crystallography.net/cod/cif/2/00/48/2004840.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_2004840 loop_ _publ_author_name 'Blackburn, A. C.' 'Dobson, A. J.' 'Gerkin, R. E.' _publ_section_title ; Bis(pyridinium) Pamoate ; _journal_issue 5 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first 1269 _journal_page_last 1272 _journal_paper_doi 10.1107/S0108270195015691 _journal_volume 52 _journal_year 1996 _chemical_formula_iupac '2C5 H6 N + , C23 H14 O6 2-' _chemical_formula_moiety '2(C5 H6 N) + , C23 H14 O6 2-' _chemical_formula_sum 'C33 H26 N2 O6' _chemical_formula_weight 546.58 _chemical_name_common 'Pamoic acid . 2pyridine' _chemical_name_systematic ' ?' _space_group_IT_number 2 _symmetry_cell_setting triclinic _symmetry_space_group_name_Hall '-P 1' _symmetry_space_group_name_H-M 'P -1' _cell_angle_alpha 99.29(2) _cell_angle_beta 101.75(2) _cell_angle_gamma 98.76(1) _cell_formula_units_Z 2 _cell_length_a 11.276(2) _cell_length_b 16.599(3) _cell_length_c 7.516(2) _cell_measurement_reflns_used 25 _cell_measurement_temperature 296 _cell_measurement_theta_max 17.4 _cell_measurement_theta_min 12.7 _cell_volume 1334.0(5) _computing_cell_refinement 'MSC/AFC Diffractometer Control Software' _computing_data_collection ;MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1988) ; _computing_data_reduction 'TEXSAN (Molecular Structure Corporation, 1989)' _computing_molecular_graphics 'ORTEPII (Johnson, 1976)' _computing_publication_material TEXSAN _computing_structure_refinement TEXSAN _computing_structure_solution 'MITHRIL (Gilmore, 1984)' _diffrn_ambient_temperature 296 _diffrn_measurement_device AFC5S _diffrn_measurement_method 'omega scans ' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'X-ray tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.012 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_number 6450 _diffrn_reflns_theta_max 27.50 _diffrn_reflns_theta_min 2.00 _diffrn_standards_decay_% 0 _diffrn_standards_interval_count 150 _diffrn_standards_number 6 _exptl_absorpt_coefficient_mu 0.088 _exptl_absorpt_correction_type none _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.361 _exptl_crystal_density_meas ? _exptl_crystal_description 'cut chunk' _exptl_crystal_F_000 572 _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.38 _exptl_crystal_size_min 0.26 _refine_diff_density_max '0.32; next highest, 0.16' _refine_diff_density_min -0.17 _refine_ls_extinction_coef 2.2E-6(2) _refine_ls_extinction_method 'Zachariasen (1963,1968)' _refine_ls_goodness_of_fit_obs 1.80 _refine_ls_hydrogen_treatment 'see text' _refine_ls_matrix_type full _refine_ls_number_parameters 392 _refine_ls_number_reflns 2968 _refine_ls_R_factor_obs 0.045 _refine_ls_shift/esd_max 'less than 0.01' _refine_ls_structure_factor_coef F _refine_ls_weighting_details w=\s~F~^-2^ _refine_ls_weighting_scheme calc _refine_ls_wR_factor_obs 0.053 _reflns_number_observed 2968 _reflns_number_total 6136 _reflns_observed_criterion 'I > 3\s(I)' _cod_data_source_file bk1191.cif _cod_data_source_block pyridinium_pamoate _cod_depositor_comments ; The following automatic conversions were performed: '_exptl_crystal_density_meas' value 'none' was changed to '?' - the value is perceived as not measured. Automatic conversion script Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas The following automatic conversions were performed: '_refine_ls_weighting_scheme' value 'w=\s~F~^-2^' was changed to 'calc'. New tag '_refine_ls_weighting_details' was created. The value of the new tag was set to 'w=\s~F~^-2^'. Automatic conversion script Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas ; _cod_database_code 2004840 loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z 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 O1 0.080(2) 0.067(2) 0.098(2) 0.0300(10) 0.0200(10) 0.0280(10) O1A 0.0550(10) 0.0750(10) 0.0740(10) 0.0220(10) 0.0160(10) -0.0100(10) O2 0.110(2) 0.095(2) 0.100(2) 0.062(2) 0.033(2) 0.033(2) O2A 0.0600(10) 0.0660(10) 0.101(2) 0.0240(10) 0.0230(10) 0.0010(10) O3 0.0640(10) 0.108(2) 0.111(2) 0.0390(10) 0.0130(10) -0.0080(10) O3A 0.0590(10) 0.109(2) 0.101(2) 0.0420(10) 0.0100(10) 0.0160(10) N1 0.0510(10) 0.063(2) 0.067(2) 0.0190(10) 0.0070(10) 0.0120(10) N2 0.068(2) 0.069(2) 0.068(2) 0.0320(10) 0.0000(10) -0.0020(10) C1 0.051(2) 0.058(2) 0.041(2) 0.0170(10) 0.0080(10) 0.0050(10) C1A 0.0390(10) 0.0450(10) 0.057(2) 0.0040(10) 0.0140(10) 0.0090(10) C2 0.057(2) 0.060(2) 0.052(2) 0.0190(10) 0.0070(10) 0.0080(10) C2A 0.0410(10) 0.046(2) 0.064(2) 0.0030(10) 0.0140(10) 0.0010(10) C3 0.060(2) 0.069(2) 0.048(2) 0.027(2) 0.0050(10) 0.0010(10) C3A 0.0380(10) 0.047(2) 0.075(2) 0.0050(10) 0.0150(10) 0.0090(10) C4 0.044(2) 0.085(2) 0.054(2) 0.018(2) 0.0080(10) -0.005(2) C4A 0.0380(10) 0.059(2) 0.067(2) 0.0040(10) 0.0080(10) 0.0110(10) C5 0.055(2) 0.080(2) 0.075(2) 0.001(2) 0.009(2) 0.001(2) C5A 0.054(2) 0.071(2) 0.058(2) 0.008(2) 0.0090(10) 0.003(2) C6 0.073(2) 0.060(2) 0.084(2) -0.001(2) 0.006(2) 0.004(2) C6A 0.063(2) 0.065(2) 0.067(2) 0.010(2) 0.019(2) -0.006(2) C7 0.075(2) 0.058(2) 0.070(2) 0.019(2) 0.005(2) 0.001(2) C7A 0.060(2) 0.051(2) 0.077(2) 0.0150(10) 0.024(2) 0.002(2) C8 0.052(2) 0.056(2) 0.056(2) 0.0150(10) 0.0060(10) -0.0010(10) C8A 0.047(2) 0.047(2) 0.065(2) 0.0080(10) 0.0150(10) 0.0090(10) C9 0.0470(10) 0.054(2) 0.0380(10) 0.0120(10) 0.0040(10) -0.0020(10) C9A 0.0380(10) 0.0400(10) 0.060(2) 0.0020(10) 0.0160(10) 0.0080(10) C10 0.044(2) 0.064(2) 0.047(2) 0.0070(10) 0.0050(10) -0.0030(10) C10A 0.0370(10) 0.049(2) 0.061(2) 0.0030(10) 0.0140(10) 0.0060(10) C11 0.052(2) 0.056(2) 0.055(2) 0.0130(10) 0.0160(10) 0.0090(10) C12 0.070(2) 0.100(3) 0.054(2) 0.041(2) 0.007(2) 0.003(2) C12A 0.040(2) 0.054(2) 0.090(2) 0.0080(10) 0.015(2) 0.012(2) C13 0.084(2) 0.060(2) 0.092(3) 0.018(2) 0.019(2) 0.029(2) C14 0.061(2) 0.106(3) 0.102(3) 0.000(2) 0.021(2) 0.047(2) C15 0.057(2) 0.148(4) 0.076(2) 0.041(2) 0.019(2) 0.029(2) C16 0.078(3) 0.084(3) 0.116(3) 0.043(2) 0.012(2) 0.003(2) C17 0.067(2) 0.053(2) 0.108(3) 0.011(2) 0.008(2) 0.005(2) C18 0.056(2) 0.065(2) 0.092(3) 0.007(2) 0.008(2) 0.009(2) C19 0.056(2) 0.082(2) 0.092(2) 0.019(2) 0.020(2) 0.019(2) C20 0.068(2) 0.067(2) 0.073(2) 0.032(2) 0.017(2) 0.014(2) C21 0.081(2) 0.063(2) 0.080(2) 0.022(2) 0.020(2) 0.024(2) C22 0.066(2) 0.101(3) 0.065(2) 0.027(2) 0.021(2) 0.021(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_thermal_displace_type _atom_site_type_symbol O1 0.1440(2) 0.1287(1) 0.8762(3) 0.0786(8) Uij O O1A -0.2077(2) 0.3306(1) 0.8103(3) 0.0696(7) Uij O O2 0.3520(2) 0.0901(2) 0.8723(3) 0.0942(10) Uij O O2A -0.3991(2) 0.3734(1) 0.6336(3) 0.0754(7) Uij O O3 0.5033(2) 0.1814(2) 0.8313(3) 0.0962(9) Uij O O3A -0.4652(2) 0.3259(1) 0.3296(3) 0.0886(8) Uij O N1 -0.3260(2) 0.6359(2) 0.6675(3) 0.0602(8) Uij N N2 -0.5832(2) -0.0452(2) 0.2660(3) 0.0704(9) Uij N C1 0.1147(2) 0.2631(2) 0.8396(3) 0.0501(8) Uij C C1A -0.1095(2) 0.2369(2) 0.6486(3) 0.0472(8) Uij C C2 0.1920(3) 0.2069(2) 0.8579(4) 0.0567(9) Uij C C2A -0.2009(2) 0.2845(2) 0.6473(4) 0.0516(8) Uij C C3 0.3176(3) 0.2273(2) 0.8536(4) 0.0600(9) Uij C C3A -0.2873(2) 0.2852(2) 0.4817(4) 0.0539(8) Uij C C4 0.3656(2) 0.3063(2) 0.8438(4) 0.0631(9) Uij C C4A -0.2790(2) 0.2395(2) 0.3178(4) 0.0562(8) Uij C C5 0.3441(3) 0.4522(2) 0.8442(4) 0.074(1) Uij C C5A -0.1872(3) 0.1378(2) 0.1430(4) 0.0630(9) Uij C C6 0.2768(3) 0.5129(2) 0.8538(4) 0.077(1) Uij C C6A -0.1090(3) 0.0837(2) 0.1374(4) 0.0667(10) Uij C C7 0.1515(3) 0.4918(2) 0.8562(4) 0.070(1) Uij C C7A -0.0299(3) 0.0775(2) 0.3021(4) 0.0625(9) Uij C C8 0.0966(2) 0.4115(2) 0.8461(4) 0.0562(8) Uij C C8A -0.0278(2) 0.1267(2) 0.4679(4) 0.0529(8) Uij C C9 0.1663(2) 0.3470(2) 0.8394(3) 0.0487(8) Uij C C9A -0.1083(2) 0.1849(1) 0.4782(4) 0.0465(7) Uij C C10 0.2928(2) 0.3687(2) 0.8407(3) 0.0545(8) Uij C C10A -0.1904(2) 0.1884(2) 0.3115(4) 0.0501(8) Uij C C11 -0.0219(3) 0.2359(2) 0.8296(4) 0.0538(9) Uij C C12 0.3947(3) 0.1604(3) 0.8555(4) 0.074(1) Uij C C12A -0.3908(3) 0.3322(2) 0.4843(5) 0.0614(9) Uij C C13 -0.2392(3) 0.7016(2) 0.6837(4) 0.077(1) Uij C C14 -0.1225(3) 0.6941(2) 0.6763(5) 0.088(1) Uij C C15 -0.0947(3) 0.6174(3) 0.6521(5) 0.090(1) Uij C C16 -0.1819(4) 0.5504(2) 0.6424(5) 0.093(1) Uij C C17 -0.2987(3) 0.5611(2) 0.6491(5) 0.079(1) Uij C C18 -0.6713(3) -0.0551(2) 0.3571(5) 0.074(1) Uij C C19 -0.7202(3) 0.0087(2) 0.4263(5) 0.075(1) Uij C C20 -0.6784(3) 0.0859(2) 0.4023(4) 0.067(1) Uij C C21 -0.5873(3) 0.0989(2) 0.3107(4) 0.073(1) Uij C C22 -0.5397(3) 0.0313(2) 0.2432(4) 0.075(1) Uij C H11A -0.038(2) 0.178(2) 0.853(3) 0.056(8) Uiso H H11B -0.044(2) 0.272(1) 0.926(3) 0.056(8) Uiso H H1 -0.421(3) 0.650(2) 0.669(4) 0.12(1) Uiso H H2 -0.5324 -0.1005 0.2098 0.20(2) Uiso H H3 0.204(3) 0.105(2) 0.869(5) 0.10(1) Uiso H H3A -0.273(3) 0.354(2) 0.793(4) 0.10(1) Uiso H H4 0.452348 0.320307 0.838812 ? Uiso H H4A -0.335693 0.242429 0.202452 ? Uiso H H5 0.430881 0.466528 0.839472 ? Uiso H H5A -0.242742 0.141977 0.027734 ? Uiso H H6 0.314698 0.570674 0.859082 ? Uiso H H6A -0.107803 0.049131 0.019188 ? Uiso H H7 0.102607 0.535685 0.865273 ? Uiso H H7A 0.025029 0.037196 0.298732 ? Uiso H H8 0.008491 0.398121 0.843373 ? Uiso H H8A 0.029713 0.121939 0.580781 ? Uiso H H13 -0.259857 0.757109 0.701522 ? Uiso H H14 -0.059216 0.743465 0.688201 ? Uiso H H15 -0.011469 0.610389 0.641647 ? Uiso H H16 -0.161722 0.494741 0.630761 ? Uiso H H17 -0.362884 0.512661 0.640070 ? Uiso H H18 -0.702218 -0.111004 0.374937 ? Uiso H H19 -0.785421 -0.000798 0.493332 ? Uiso H H20 -0.713900 0.132702 0.451129 ? Uiso H H21 -0.556027 0.154764 0.292865 ? Uiso H H22 -0.473277 0.039417 0.177877 ? Uiso H loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source H 0 0 'Stewart, Davidson and Simpson (1965)' C .002 .002 'Cromer and Waber (1974)' O .008 .006 'Cromer and Waber (1974)' N .004 .003 'Cromer and Waber (1974)' loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l 0 1 1 3 1 -1 1 -6 0 2 7 -1 4 -5 3 5 8 -2 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 C2 O1 H3 101(2) yes C2A O1A H3A 110(2) yes C2 C1 C9 118.7(2) yes C2 C1 C11 119.7(3) yes C9 C1 C11 121.6(2) yes C2A C1A C9A 117.9(2) yes C2A C1A C11 120.0(2) yes C9A C1A C11 121.9(2) yes O1 C2 C1 118.4(3) yes O1 C2 C3 119.8(2) yes C1 C2 C3 121.8(3) yes O1A C2A C1A 118.6(2) yes O1A C2A C3A 119.6(2) yes C1A C2A C3A 121.9(2) yes C2 C3 C4 119.2(3) yes C2 C3 C12 119.3(3) yes C4 C3 C12 121.5(3) yes C2A C3A C4A 119.3(2) yes C2A C3A C12A 121.3(3) yes C4A C3A C12A 119.4(3) yes C3 C4 C10 121.3(3) yes C3A C4A C10A 121.3(3) yes C6 C5 C10 121.7(3) yes C6A C5A C10A 121.4(3) yes C5 C6 C7 119.0(3) yes C5A C6A C7A 119.2(3) yes C6 C7 C8 121.3(3) yes C6A C7A C8A 121.3(2) yes C7 C8 C9 120.5(3) yes C7A C8A C9A 120.8(2) yes C1 C9 C8 122.4(2) yes C1 C9 C10 119.6(2) yes C8 C9 C10 117.9(2) yes C1A C9A C8A 122.5(2) yes C1A C9A C10A 120.3(2) yes C8A C9A C10A 117.2(2) yes C4 C10 C5 121.7(3) yes C4 C10 C9 118.9(3) yes C5 C10 C9 119.4(2) yes C4A C10A C5A 120.8(2) yes C4A C10A C9A 119.1(2) yes C5A C10A C9A 120.0(2) yes C1 C11 C1A 116.1(2) yes C1 C11 H11A 110.0(10) yes C1 C11 H11B 109.0(10) yes C1A C11 H11A 107.0(10) yes C1A C11 H11B 107.0(10) yes O2 C12 O3 123.4(3) yes O2 C12 C3 121.0(3) yes O3 C12 C3 115.5(3) yes O2A C12A O3A 124.5(3) yes O2A C12A C3A 119.6(3) yes O3A C12A C3A 115.9(3) yes C13 N1 C17 119.9(3) yes N1 C13 C14 121.6(3) yes C13 C14 C15 118.8(3) yes C14 C15 C16 119.7(3) yes C15 C16 C17 119.2(3) yes C18 N2 C22 119.0(3) yes N1 C17 C16 120.7(3) yes N2 C18 C19 122.4(3) yes C18 C19 C20 119.3(3) yes C19 C20 C21 120.2(3) yes C20 C21 C22 118.2(3) yes N2 C22 C21 120.9(3) yes loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag O1 C2 1.367(3) yes O1A C2A 1.359(3) yes O2 C12 1.230(4) yes O2A C12A 1.245(3) yes O3 C12 1.278(4) yes O3A C12A 1.266(3) yes C1 C2 1.375(3) yes C1 C9 1.426(3) yes C1 C11 1.520(4) yes C1A C2A 1.390(3) yes C1A C9A 1.428(3) yes C1A C11 1.514(4) yes C2 C3 1.414(4) yes C2A C3A 1.419(4) yes C3 C4 1.359(4) yes C3A C4A 1.366(4) yes C4 C10 1.418(4) yes C4A C10A 1.410(3) yes C5 C6 1.352(4) yes C5A C6A 1.352(4) yes C6 C7 1.408(4) yes C6A C7A 1.399(4) yes C7 C8 1.365(4) yes C7A C8A 1.369(3) yes C8 C9 1.421(3) yes C8A C9A 1.426(3) yes C9 C10 1.414(3) yes C9A C10A 1.413(3) yes C11 H11A 1.00(2) yes C11 H11B 0.97(2) yes C4 H4 0.980 yes C4A H4A 0.980 yes C5 H5 0.980 yes C5A H5A 0.980 yes C6 H6 0.980 yes C6A H6A 0.980 yes C7 H7 0.980 yes C7A H7A 0.980 yes C8 H8 0.980 yes C8A H8A 0.980 yes N1 C13 1.322(4) yes N1 C17 1.316(3) yes C13 C14 1.352(4) yes C14 C15 1.350(5) yes C15 C16 1.349(5) yes C16 C17 1.365(4) yes C16 H16 0.980 yes C17 H17 0.980 yes N2 C18 1.321(4) yes N2 C22 1.340(4) yes C18 C19 1.347(4) yes C19 C20 1.350(4) yes C20 C21 1.359(4) yes C21 C22 1.385(4) yes C18 H18 0.980 yes C19 H19 0.980 yes C20 H20 0.980 yes C21 H21 0.980 yes C22 H22 0.980 yes