#------------------------------------------------------------------------------ #$Date: 2011-09-17 23:27:16 +0300 (Sat, 17 Sep 2011) $ #$Revision: 26029 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/2225405.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_2225405 loop_ _publ_author_name 'Hemamalini, Madhukar' 'Fun, Hoong-Kun' _publ_section_title ; 2-Amino-5-chloropyridine--benzoic acid (1/1) ; _journal_coeditor_code WN2376 _journal_issue 3 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o578 _journal_volume 66 _journal_year 2010 _chemical_formula_iupac 'C5 H5 Cl N2, C7 H6 O2' _chemical_formula_moiety 'C5 H5 Cl N2, C7 H6 O2' _chemical_formula_sum 'C12 H11 Cl N2 O2' _chemical_formula_weight 250.68 _chemical_name_systematic ; 2-Amino-5-chloropyridine--benzoic acid (1/1) ; _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 100.161(2) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 17.6114(19) _cell_length_b 5.3442(6) _cell_length_c 12.4774(13) _cell_measurement_reflns_used 5100 _cell_measurement_temperature 100.00(10) _cell_measurement_theta_max 29.97 _cell_measurement_theta_min 2.35 _cell_volume 1155.9(2) _computing_cell_refinement 'SAINT (Bruker, 2009)' _computing_data_collection 'APEX2 (Bruker, 2009)' _computing_data_reduction 'SAINT (Bruker, 2009)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 2008)' _computing_publication_material 'SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009)' _computing_structure_refinement 'SHELXTL (Sheldrick, 2008)' _computing_structure_solution 'SHELXTL (Sheldrick, 2008)' _diffrn_ambient_temperature 100.00(10) _diffrn_measured_fraction_theta_full 0.986 _diffrn_measured_fraction_theta_max 0.986 _diffrn_measurement_device_type ; Bruker SMART APEX DUO CCD area-detector diffractometer ; _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 0.0254 _diffrn_reflns_av_sigmaI/netI 0.0263 _diffrn_reflns_limit_h_max 24 _diffrn_reflns_limit_h_min -24 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_number 11852 _diffrn_reflns_theta_full 30.02 _diffrn_reflns_theta_max 30.02 _diffrn_reflns_theta_min 1.17 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.321 _exptl_absorpt_correction_T_max 0.9785 _exptl_absorpt_correction_T_min 0.8436 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SADABS; Bruker, 2009)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.440 _exptl_crystal_density_method 'not measured' _exptl_crystal_description plate _exptl_crystal_F_000 520 _exptl_crystal_size_max 0.55 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.07 _refine_diff_density_max 0.461 _refine_diff_density_min -0.210 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.116 _refine_ls_hydrogen_treatment refall _refine_ls_matrix_type full _refine_ls_number_parameters 198 _refine_ls_number_reflns 3331 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.116 _refine_ls_R_factor_all 0.0417 _refine_ls_R_factor_gt 0.0328 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean <0.001 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0596P)^2^+0.2767P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0959 _refine_ls_wR_factor_ref 0.1105 _reflns_number_gt 2802 _reflns_number_total 3331 _reflns_threshold_expression >2(I) _[local]_cod_data_source_file wn2376.cif _[local]_cod_data_source_block I _[local]_cod_cif_authors_sg_H-M 'P 21/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. '_geom_hbond_publ_flag' value 'Yes' changed to 'yes' 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 2225405 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_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 _atom_site_disorder_assembly _atom_site_disorder_group Cl Cl1 0.029115(18) 0.29660(7) 0.17435(3) 0.02611(11) Uani d . 1 . . N N1 0.17431(6) -0.2004(2) 0.08617(9) 0.0197(2) Uani d . 1 . . N N2 0.22948(8) -0.2526(3) -0.06737(10) 0.0270(3) Uani d . 1 . . C C1 0.12668(7) -0.0733(2) 0.14079(10) 0.0202(2) Uani d . 1 . . C C2 0.08720(7) 0.1356(2) 0.09858(10) 0.0203(2) Uani d . 1 . . C C3 0.09605(8) 0.2235(3) -0.00426(11) 0.0232(3) Uani d . 1 . . C C4 0.14399(8) 0.0960(3) -0.06017(11) 0.0229(3) Uani d . 1 . . C C5 0.18308(7) -0.1193(2) -0.01300(10) 0.0199(2) Uani d . 1 . . O O1 0.30023(6) 0.33873(19) 0.06701(7) 0.0235(2) Uani d . 1 . . O O2 0.25316(5) 0.46305(18) 0.21358(7) 0.0202(2) Uani d . 1 . . C C6 0.35843(7) 0.1449(3) 0.34708(10) 0.0194(2) Uani d . 1 . . C C7 0.40642(7) -0.0304(3) 0.40807(10) 0.0226(3) Uani d . 1 . . C C8 0.44122(8) -0.2180(3) 0.35634(12) 0.0232(3) Uani d . 1 . . C C9 0.42870(8) -0.2295(3) 0.24289(12) 0.0227(3) Uani d . 1 . . C C10 0.38163(7) -0.0544(2) 0.18193(10) 0.0202(2) Uani d . 1 . . C C11 0.34623(7) 0.1339(2) 0.23375(10) 0.0170(2) Uani d . 1 . . C C12 0.29775(7) 0.3214(2) 0.16423(10) 0.0173(2) Uani d . 1 . . H H1 0.1213(10) -0.132(3) 0.2126(14) 0.028(4) Uiso d . 1 . . H H3 0.0695(11) 0.375(4) -0.0377(16) 0.040(5) Uiso d . 1 . . H H4 0.1539(10) 0.154(4) -0.1271(15) 0.032(5) Uiso d . 1 . . H H6 0.3370(10) 0.270(4) 0.3810(14) 0.026(4) Uiso d . 1 . . H H7 0.4150(10) -0.018(4) 0.4848(14) 0.032(5) Uiso d . 1 . . H H8 0.4762(10) -0.344(3) 0.4016(14) 0.026(4) Uiso d . 1 . . H H9 0.4506(10) -0.362(3) 0.2061(14) 0.029(4) Uiso d . 1 . . H H10 0.3722(9) -0.058(3) 0.1028(13) 0.024(4) Uiso d . 1 . . H H1O2 0.2262(13) 0.590(5) 0.1647(19) 0.061(7) Uiso d . 1 . . H H1N2 0.2563(11) -0.378(4) -0.0353(16) 0.039(5) Uiso d . 1 . . H H2N2 0.2443(11) -0.186(4) -0.1250(16) 0.033(5) Uiso d . 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 Cl1 0.02624(17) 0.02425(18) 0.02760(18) 0.00709(12) 0.00407(12) 0.00036(12) N1 0.0220(5) 0.0181(5) 0.0187(5) 0.0018(4) 0.0026(4) 0.0026(4) N2 0.0345(6) 0.0266(6) 0.0217(5) 0.0075(5) 0.0096(5) 0.0059(5) C1 0.0208(5) 0.0187(6) 0.0208(6) 0.0005(5) 0.0025(4) 0.0021(5) C2 0.0185(5) 0.0186(6) 0.0228(6) 0.0008(5) 0.0011(4) -0.0009(5) C3 0.0232(6) 0.0200(6) 0.0240(6) 0.0016(5) -0.0028(5) 0.0040(5) C4 0.0249(6) 0.0229(6) 0.0193(6) 0.0005(5) -0.0006(5) 0.0049(5) C5 0.0208(5) 0.0189(6) 0.0193(5) -0.0018(5) 0.0012(4) 0.0010(5) O1 0.0320(5) 0.0243(5) 0.0148(4) 0.0045(4) 0.0059(3) 0.0020(4) O2 0.0225(4) 0.0211(4) 0.0178(4) 0.0043(4) 0.0055(3) 0.0031(4) C6 0.0207(5) 0.0203(6) 0.0182(5) 0.0006(5) 0.0063(4) 0.0022(5) C7 0.0219(6) 0.0267(7) 0.0191(6) 0.0010(5) 0.0037(4) 0.0056(5) C8 0.0197(6) 0.0206(6) 0.0291(7) 0.0010(5) 0.0034(5) 0.0065(5) C9 0.0210(6) 0.0182(6) 0.0289(7) 0.0010(5) 0.0044(5) -0.0018(5) C10 0.0210(5) 0.0195(6) 0.0200(5) -0.0013(5) 0.0033(4) -0.0026(5) C11 0.0165(5) 0.0158(5) 0.0187(5) -0.0029(4) 0.0030(4) 0.0015(4) C12 0.0179(5) 0.0167(6) 0.0172(5) -0.0025(4) 0.0027(4) 0.0001(4) 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_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C5 N1 C1 . . 118.92(11) ? C5 N2 H1N2 . . 120.0(13) ? C5 N2 H2N2 . . 119.3(13) ? H1N2 N2 H2N2 . . 117.8(18) ? N1 C1 C2 . . 122.21(12) ? N1 C1 H1 . . 118.2(11) ? C2 C1 H1 . . 119.5(11) ? C1 C2 C3 . . 119.61(12) ? C1 C2 Cl1 . . 120.10(10) ? C3 C2 Cl1 . . 120.25(10) ? C4 C3 C2 . . 118.61(12) ? C4 C3 H3 . . 118.7(11) ? C2 C3 H3 . . 122.6(11) ? C3 C4 C5 . . 119.45(12) ? C3 C4 H4 . . 121.2(11) ? C5 C4 H4 . . 119.3(11) ? N1 C5 N2 . . 117.98(12) ? N1 C5 C4 . . 121.20(12) ? N2 C5 C4 . . 120.81(12) ? C12 O2 H1O2 . . 111.7(14) ? C11 C6 C7 . . 119.69(12) ? C11 C6 H6 . . 120.1(11) ? C7 C6 H6 . . 120.1(11) ? C8 C7 C6 . . 120.33(12) ? C8 C7 H7 . . 120.9(11) ? C6 C7 H7 . . 118.7(11) ? C7 C8 C9 . . 119.92(12) ? C7 C8 H8 . . 119.6(10) ? C9 C8 H8 . . 120.5(10) ? C10 C9 C8 . . 119.96(12) ? C10 C9 H9 . . 119.2(11) ? C8 C9 H9 . . 120.8(11) ? C9 C10 C11 . . 120.26(12) ? C9 C10 H10 . . 121.5(10) ? C11 C10 H10 . . 118.3(10) ? C6 C11 C10 . . 119.82(12) ? C6 C11 C12 . . 122.12(11) ? C10 C11 C12 . . 118.04(11) ? O1 C12 O2 . . 123.17(11) ? O1 C12 C11 . . 120.66(11) ? O2 C12 C11 . . 116.17(10) ? 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 C2 . 1.7382(13) ? N1 C5 . 1.3454(16) ? N1 C1 . 1.3532(17) ? N2 C5 . 1.3530(18) ? N2 H1N2 . 0.88(2) ? N2 H2N2 . 0.881(19) ? C1 C2 . 1.3705(18) ? C1 H1 . 0.970(18) ? C2 C3 . 1.4006(19) ? C3 C4 . 1.368(2) ? C3 H3 . 0.99(2) ? C4 C5 . 1.4149(18) ? C4 H4 . 0.936(18) ? O1 C12 . 1.2250(15) ? O2 C12 . 1.3190(15) ? O2 H1O2 . 0.98(2) ? C6 C11 . 1.3936(17) ? C6 C7 . 1.3946(18) ? C6 H6 . 0.907(18) ? C7 C8 . 1.392(2) ? C7 H7 . 0.945(17) ? C8 C9 . 1.395(2) ? C8 H8 . 1.015(18) ? C9 C10 . 1.3854(19) ? C9 H9 . 0.962(18) ? C10 C11 . 1.4005(18) ? C10 H10 . 0.972(16) ? C11 C12 . 1.4913(17) ? 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 O2 H1O2 N1 1_565 0.98(2) 1.65(2) 2.6290(10) 175(2) yes N2 H1N2 O1 1_545 0.88(2) 2.04(2) 2.898(2) 165.4(18) yes N2 H2N2 O2 4_565 0.88(2) 2.37(2) 3.231(2) 165.8(17) yes C3 H3 Cl1 3_565 0.99(2) 2.82(2) 3.780(2) 163.4(16) yes C6 H6 O1 4_566 0.91(2) 2.58(2) 3.095(2) 116.3(15) yes 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_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion _geom_torsion_publ_flag C5 N1 C1 C2 . . . . -0.16(19) ? N1 C1 C2 C3 . . . . -0.2(2) ? N1 C1 C2 Cl1 . . . . -178.03(10) ? C1 C2 C3 C4 . . . . 0.34(19) ? Cl1 C2 C3 C4 . . . . 178.12(10) ? C2 C3 C4 C5 . . . . -0.04(19) ? C1 N1 C5 N2 . . . . -178.39(12) ? C1 N1 C5 C4 . . . . 0.47(19) ? C3 C4 C5 N1 . . . . -0.37(19) ? C3 C4 C5 N2 . . . . 178.46(13) ? C11 C6 C7 C8 . . . . -0.9(2) ? C6 C7 C8 C9 . . . . 0.6(2) ? C7 C8 C9 C10 . . . . 0.0(2) ? C8 C9 C10 C11 . . . . -0.3(2) ? C7 C6 C11 C10 . . . . 0.60(19) ? C7 C6 C11 C12 . . . . -177.84(11) ? C9 C10 C11 C6 . . . . -0.01(19) ? C9 C10 C11 C12 . . . . 178.49(11) ? C6 C11 C12 O1 . . . . 165.21(12) ? C10 C11 C12 O1 . . . . -13.25(18) ? C6 C11 C12 O2 . . . . -14.87(17) ? C10 C11 C12 O2 . . . . 166.67(11) ?