#------------------------------------------------------------------------------ #$Date: 2015-01-23 14:30:19 +0200 (Fri, 23 Jan 2015) $ #$Revision: 130086 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/01/26/2012630.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_2012630 loop_ _publ_author_name 'Sugiyama, Teruki' 'Meng, Jiben' 'Matsuura, Teruo' _publ_section_title ; Two-component molecular crystals composed of chloronitrobenzoic acids and 4-aminopyridine ; _journal_issue 4 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first o242 _journal_page_last o246 _journal_paper_doi 10.1107/S0108270102003657 _journal_volume 58 _journal_year 2002 _chemical_formula_iupac 'C5 H7 N2 + , C7 H3 Cl N O4 -' _chemical_formula_moiety 'C5 H7 N2 + , C7 H3 Cl N O4 -' _chemical_formula_sum 'C12 H10 Cl N3 O4' _chemical_formula_weight 295.68 _chemical_name_systematic ; 4-Aminopyridium 4-chloro-2-nitrobenzoate ; _space_group_IT_number 15 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-C 2yc' _symmetry_space_group_name_H-M 'C 1 2/c 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _cell_angle_alpha 90 _cell_angle_beta 103.749(14) _cell_angle_gamma 90 _cell_formula_units_Z 8 _cell_length_a 25.608(19) _cell_length_b 8.475(6) _cell_length_c 12.433(10) _cell_measurement_temperature 293(2) _cell_volume 2621(3) _computing_cell_refinement XSCANS _computing_data_collection 'XSCANS (Siemens, 1996)' _computing_data_reduction 'SHELXTL (Bruker, 1997)' _computing_molecular_graphics SHELXTL _computing_publication_material SHELXTL _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _diffrn_ambient_temperature 293(2) _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 1.000 _diffrn_measurement_device_type 'Make? Model? CCD area-detector' _diffrn_measurement_method '\f and \w scans' _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 0.028 _diffrn_reflns_av_sigmaI/netI 0.035 _diffrn_reflns_limit_h_max 26 _diffrn_reflns_limit_h_min -30 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_number 5262 _diffrn_reflns_theta_full 25.02 _diffrn_reflns_theta_max 25.02 _diffrn_reflns_theta_min 1.64 _exptl_absorpt_coefficient_mu 0.309 _exptl_absorpt_correction_T_max 0.941 _exptl_absorpt_correction_T_min 0.913 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SADABS; Sheldrick, 1995)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.499 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description prism _exptl_crystal_F_000 1216 _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.20 _refine_diff_density_max 0.23 _refine_diff_density_min -0.25 _refine_ls_extinction_coef 0.0061(7) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method 'SHELXL97 (Sheldrick, 1997)' _refine_ls_goodness_of_fit_ref 1.041 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 194 _refine_ls_number_reflns 2308 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.041 _refine_ls_R_factor_all 0.065 _refine_ls_R_factor_gt 0.037 _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^)+(0.0586P)^2^+1.1026P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.093 _refine_ls_wR_factor_ref 0.120 _reflns_number_gt 1579 _reflns_number_total 2308 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file gd1189.cif _[local]_cod_data_source_block IV _[local]_cod_cif_authors_sg_H-M 'C 2/c' _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 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_values 1715 2011-07-08 13:25:40Z adriana The following automatic conversions were performed: '_exptl_crystal_density_meas' value 'not measured' 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 ; _cod_database_code 2012630 _cod_database_fobs_code 2012630 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -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 Cl1 0.46273(3) 0.19463(9) 1.09806(7) 0.0691(3) Uani d . 1 . . Cl O1 0.67956(8) 0.5915(2) 1.03009(16) 0.0627(6) Uani d . 1 . . O O2 0.64006(7) 0.5301(2) 0.85667(16) 0.0623(6) Uani d . 1 . . O O3 0.64154(9) 0.1909(3) 0.86890(18) 0.0766(7) Uani d . 1 . . O O4 0.56335(9) 0.2125(3) 0.76201(18) 0.0929(9) Uani d . 1 . . O N1 0.67789(10) 0.7470(3) 0.73599(19) 0.0543(6) Uani d . 1 . . N H1 0.6714(13) 0.672(4) 0.785(3) 0.087(11) Uiso d . 1 . . H N2 0.71828(11) 1.0873(3) 0.5373(2) 0.0553(7) Uani d . 1 . . N H22 0.7050(12) 1.173(3) 0.530(2) 0.052(9) Uiso d . 1 . . H H21 0.7497(13) 1.077(3) 0.510(2) 0.076(10) Uiso d . 1 . . H N3 0.59496(10) 0.2314(3) 0.84955(19) 0.0499(6) Uani d . 1 . . N C1 0.72010(12) 0.7263(3) 0.6911(2) 0.0545(7) Uani d . 1 . . C H1A 0.7399 0.6334 0.7052 0.065 Uiso calc R 1 . . H C2 0.73461(10) 0.8376(3) 0.6258(2) 0.0475(7) Uani d . 1 . . C H2A 0.7645 0.8213 0.5970 0.057 Uiso calc R 1 . . H C3 0.70500(9) 0.9766(3) 0.6015(2) 0.0405(6) Uani d . 1 . . C C4 0.66046(10) 0.9934(3) 0.6484(2) 0.0500(7) Uani d . 1 . . C H4A 0.6391 1.0832 0.6341 0.060 Uiso calc R 1 . . H C5 0.64896(11) 0.8785(4) 0.7142(2) 0.0574(8) Uani d . 1 . . C H5A 0.6197 0.8918 0.7456 0.069 Uiso calc R 1 . . H C6 0.51680(10) 0.2849(3) 1.0603(2) 0.0440(6) Uani d . 1 . . C C7 0.54252(10) 0.4093(3) 1.1214(2) 0.0472(7) Uani d . 1 . . C H7A 0.5318 0.4439 1.1838 0.057 Uiso calc R 1 . . H C8 0.58457(10) 0.4825(3) 1.0888(2) 0.0437(6) Uani d . 1 . . C H8A 0.6016 0.5677 1.1297 0.052 Uiso calc R 1 . . H C9 0.60195(9) 0.4326(3) 0.99716(18) 0.0361(6) Uani d . 1 . . C C10 0.57535(9) 0.3041(3) 0.94051(19) 0.0377(6) Uani d . 1 . . C C11 0.53250(10) 0.2298(3) 0.9689(2) 0.0435(6) Uani d . 1 . . C H11A 0.5149 0.1456 0.9276 0.052 Uiso calc R 1 . . H C12 0.64452(10) 0.5254(3) 0.9582(2) 0.0430(6) Uani d . 1 . . C 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 Cl1 0.0676(5) 0.0614(5) 0.0935(7) -0.0098(4) 0.0490(4) 0.0062(4) O1 0.0603(13) 0.0647(12) 0.0681(13) -0.0248(10) 0.0255(10) -0.0151(11) O2 0.0682(13) 0.0773(13) 0.0494(12) -0.0148(11) 0.0299(9) 0.0101(10) O3 0.0678(15) 0.0954(17) 0.0710(15) 0.0281(12) 0.0255(11) -0.0145(12) O4 0.0675(15) 0.162(3) 0.0502(13) -0.0161(15) 0.0163(11) -0.0370(15) N1 0.0667(16) 0.0543(14) 0.0447(14) -0.0130(13) 0.0190(12) 0.0040(12) N2 0.0563(16) 0.0445(14) 0.0714(17) 0.0042(12) 0.0278(13) 0.0142(12) N3 0.0552(15) 0.0565(14) 0.0418(13) -0.0058(12) 0.0191(11) -0.0076(11) C1 0.0603(18) 0.0512(16) 0.0517(17) 0.0056(14) 0.0125(14) 0.0093(14) C2 0.0431(14) 0.0503(15) 0.0520(16) 0.0047(12) 0.0173(12) 0.0057(13) C3 0.0396(14) 0.0402(13) 0.0424(14) -0.0045(11) 0.0114(11) -0.0023(11) C4 0.0448(15) 0.0465(15) 0.0631(18) 0.0012(12) 0.0213(13) -0.0025(13) C5 0.0530(17) 0.0678(19) 0.0595(18) -0.0126(15) 0.0298(14) -0.0105(16) C6 0.0434(15) 0.0423(14) 0.0524(16) 0.0027(11) 0.0233(12) 0.0105(12) C7 0.0568(16) 0.0485(15) 0.0445(15) 0.0041(13) 0.0284(12) 0.0013(12) C8 0.0533(16) 0.0408(14) 0.0399(14) -0.0009(12) 0.0170(11) -0.0030(11) C9 0.0371(13) 0.0379(13) 0.0354(13) 0.0026(11) 0.0126(10) 0.0046(11) C10 0.0421(14) 0.0397(13) 0.0339(13) 0.0047(11) 0.0142(10) 0.0031(11) C11 0.0435(15) 0.0392(14) 0.0489(15) -0.0020(11) 0.0129(11) 0.0013(11) C12 0.0462(15) 0.0370(13) 0.0523(16) 0.0021(12) 0.0247(13) 0.0040(13) 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' 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 C5 N1 C1 119.4(2) no C5 N1 H1 122(2) no C1 N1 H1 118(2) no C3 N2 H22 123(2) no C3 N2 H21 121.0(18) no H22 N2 H21 115(3) no O4 N3 O3 124.2(2) no O4 N3 C10 118.1(2) no O3 N3 C10 117.7(2) no N1 C1 C2 121.5(3) no N1 C1 H1A 119.3 no C2 C1 H1A 119.3 no C1 C2 C3 120.4(2) no C1 C2 H2A 119.8 no C3 C2 H2A 119.8 no N2 C3 C2 121.6(2) no N2 C3 C4 121.8(3) no C2 C3 C4 116.6(2) no C5 C4 C3 119.6(3) no C5 C4 H4A 120.2 no C3 C4 H4A 120.2 no N1 C5 C4 122.5(3) no N1 C5 H5A 118.8 no C4 C5 H5A 118.8 no C7 C6 C11 121.5(2) no C7 C6 Cl1 119.7(2) no C11 C6 Cl1 118.8(2) no C6 C7 C8 119.2(2) no C6 C7 H7A 120.4 no C8 C7 H7A 120.4 no C7 C8 C9 121.9(2) no C7 C8 H8A 119.1 no C9 C8 H8A 119.1 no C10 C9 C8 116.3(2) no C10 C9 C12 123.4(2) no C8 C9 C12 120.1(2) no C11 C10 C9 123.6(2) no C11 C10 N3 116.1(2) no C9 C10 N3 120.1(2) no C6 C11 C10 117.5(2) no C6 C11 H11A 121.2 no C10 C11 H11A 121.2 no O1 C12 O2 126.5(2) no O1 C12 C9 117.2(2) no O2 C12 C9 116.3(2) no 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 Cl1 C6 . 1.742(3) no O1 C12 . 1.240(3) no O2 C12 . 1.241(3) no O3 N3 . 1.209(3) no O4 N3 . 1.203(3) no N1 C5 . 1.330(4) no N1 C1 . 1.340(4) no N1 H1 . 0.93(3) no N2 C3 . 1.327(3) no N2 H22 . 0.80(3) no N2 H21 . 0.95(3) no N3 C10 . 1.477(3) no C1 C2 . 1.353(4) no C1 H1A . 0.9300 no C2 C3 . 1.394(4) no C2 H2A . 0.9300 no C3 C4 . 1.406(3) no C4 C5 . 1.349(4) no C4 H4A . 0.9300 no C5 H5A . 0.9300 no C6 C7 . 1.372(4) no C6 C11 . 1.374(3) no C7 C8 . 1.384(3) no C7 H7A . 0.9300 no C8 C9 . 1.385(3) no C8 H8A . 0.9300 no C9 C10 . 1.384(3) no C9 C12 . 1.514(3) no C10 C11 . 1.382(3) no C11 H11A . 0.9300 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 N1 H1 O2 1 0.93(3) 1.79(3) 2.694(3) 164(3) yes N2 H22 O1 6_575 0.80(3) 2.10(3) 2.891(4) 172(3) yes N2 H21 O1 4_656 0.95(3) 1.99(3) 2.931(4) 169(3) yes