#------------------------------------------------------------------------------ #$Date: 2008-04-03 13:11:48 +0300 (Thu, 03 Apr 2008) $ #$Revision: 326 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/2209889.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_2209889 loop_ _publ_author_name 'Aghabozorg, Hossein' 'Ghadermazi, Mohammad' 'Attar Gharamaleki, Jafar' _publ_section_title ; Pyridine-2,6-dicarboxylic acid--pyridine-4-carboxamide--water (1/1/1) ; _journal_coeditor_code HK2083 _journal_issue 8 _journal_name_full 'Acta Crystallographica, Section E' _journal_page_first o3445 _journal_page_last o3447 _journal_volume 62 _journal_year 2006 _chemical_formula_iupac 'C7 H5 N O4, C6 H6 N2 O, H2 O' _chemical_formula_moiety 'C7 H5 N O4, C6 H6 N2 O, H2 O' _chemical_formula_sum 'C13 H13 N3 O6' _chemical_formula_weight 307.26 _chemical_name_systematic ; Pyridine-2,6-dicarboxylic acid--pyridine-4-carboxamide--water (1/1/1) ; _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_space_group_name_H-M 'P 21/c ' _atom_sites_solution_hydrogens difmap _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-97 _cell_angle_alpha 90.00 _cell_angle_beta 100.85(3) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 13.410(3) _cell_length_b 5.0467(10) _cell_length_c 19.937(4) _cell_measurement_reflns_used 24 _cell_measurement_temperature 173(2) _cell_measurement_theta_max 15 _cell_measurement_theta_min 12 _cell_volume 1325.2(5) _computing_cell_refinement P3/PC _computing_data_collection 'P3/PC (Siemens, 1989)' _computing_data_reduction P3/PC _computing_molecular_graphics SHELXTL _computing_publication_material SHELXTL _computing_structure_refinement SHELXTL _computing_structure_solution 'SHELXTL (Sheldrick, 1998)' _diffrn_ambient_temperature 173(2) _diffrn_measured_fraction_theta_full 0.996 _diffrn_measured_fraction_theta_max 0.996 _diffrn_measurement_device_type 'Rebuilt Syntex P2~1~/Siemens P3 four-circle' _diffrn_measurement_method \w/2\q _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 0.0605 _diffrn_reflns_av_sigmaI/netI 0.0478 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_h_min -4 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_number 5684 _diffrn_reflns_theta_full 27.00 _diffrn_reflns_theta_max 27.00 _diffrn_reflns_theta_min 1.55 _diffrn_standards_decay_% 2 _diffrn_standards_interval_count 98 _diffrn_standards_number 2 _exptl_absorpt_coefficient_mu 0.124 _exptl_absorpt_correction_type none _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.540 _exptl_crystal_density_method 'not measured' _exptl_crystal_description prism _exptl_crystal_F_000 640 _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _refine_diff_density_max 0.427 _refine_diff_density_min -0.416 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.004 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 205 _refine_ls_number_reflns 2895 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.004 _refine_ls_R_factor_all 0.0779 _refine_ls_R_factor_gt 0.0624 _refine_ls_shift/su_max 0.010 _refine_ls_shift/su_mean 0.001 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.045P)^2^+2.9P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1451 _refine_ls_wR_factor_ref 0.1531 _reflns_number_gt 2310 _reflns_number_total 2895 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file hk2083.cif 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_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' 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 O O1W 0.08098(16) 0.3241(5) 0.22132(10) 0.0431(6) Uani d . 1 H H1WB 0.1120 0.1905 0.2365 0.037(9) Uiso d R 1 H H1WA 0.0785 0.4452 0.2484 0.095(18) Uiso d R 1 O O1 0.36124(14) 0.0143(4) 0.52099(8) 0.0326(5) Uani d . 1 O O2 0.38700(13) 0.1147(4) 0.63184(8) 0.0264(4) Uani d . 1 H H2O 0.4283 -0.0068 0.6383 0.041(10) Uiso d R 1 O O3 0.09978(13) 0.4557(4) 0.36580(8) 0.0288(4) Uani d . 1 O O4 0.01775(13) 0.7982(4) 0.40153(8) 0.0273(4) Uani d . 1 H H4O -0.0052 0.8026 0.3604 0.052(11) Uiso d R 1 O O5 0.20533(14) -0.0903(4) 0.26934(8) 0.0306(5) Uani d . 1 N N1 0.20978(14) 0.3877(4) 0.49467(9) 0.0206(4) Uani d . 1 N N2 0.47803(14) -0.7460(5) 0.35303(10) 0.0228(5) Uani d . 1 N N3 0.24298(15) 0.0180(5) 0.38128(10) 0.0237(5) Uani d . 1 H H3NB 0.2774 0.0011 0.4226 0.037(9) Uiso d R 1 H H3NA 0.2011 0.1513 0.3754 0.021(7) Uiso d R 1 C C1 0.25959(17) 0.3530(5) 0.55901(11) 0.0200(5) Uani d . 1 C C2 0.23845(18) 0.4980(6) 0.61428(11) 0.0245(5) Uani d . 1 H H2A 0.2747 0.4653 0.6592 0.029 Uiso calc R 1 C C4 0.11269(18) 0.7317(6) 0.53601(12) 0.0248(5) Uani d . 1 H H4A 0.0618 0.8642 0.5262 0.030 Uiso calc R 1 C C3 0.16392(19) 0.6895(6) 0.60241(12) 0.0267(6) Uani d . 1 H H3A 0.1479 0.7911 0.6391 0.032 Uiso calc R 1 C C5 0.13795(17) 0.5740(5) 0.48397(11) 0.0210(5) Uani d . 1 C C6 0.34102(17) 0.1423(5) 0.56853(11) 0.0215(5) Uani d . 1 C C7 0.08344(17) 0.6033(5) 0.41085(11) 0.0208(5) Uani d . 1 C C8 0.33364(17) -0.3432(5) 0.33889(11) 0.0195(5) Uani d . 1 C C9 0.38933(19) -0.4118(6) 0.40281(12) 0.0256(5) Uani d . 1 H H9A 0.3790 -0.3205 0.4426 0.031 Uiso calc R 1 C C10 0.45953(19) -0.6139(6) 0.40755(12) 0.0267(6) Uani d . 1 H H10A 0.4963 -0.6613 0.4514 0.032 Uiso calc R 1 C C11 0.42407(19) -0.6817(6) 0.29138(12) 0.0254(5) Uani d . 1 H H11A 0.4360 -0.7764 0.2525 0.030 Uiso calc R 1 C C12 0.35192(18) -0.4830(5) 0.28251(11) 0.0236(5) Uani d . 1 H H12A 0.3151 -0.4424 0.2382 0.028 Uiso calc R 1 C C13 0.25498(17) -0.1258(5) 0.32783(11) 0.0213(5) Uani 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 O1W 0.0513(13) 0.0469(14) 0.0232(9) 0.0201(11) -0.0138(9) -0.0071(10) O1 0.0316(9) 0.0500(13) 0.0145(8) 0.0176(9) 0.0002(7) -0.0030(8) O2 0.0264(9) 0.0374(11) 0.0138(8) 0.0128(8) -0.0004(6) 0.0012(7) O3 0.0298(9) 0.0386(11) 0.0159(8) 0.0100(8) -0.0014(7) -0.0025(8) O4 0.0257(9) 0.0379(11) 0.0161(8) 0.0094(8) -0.0023(6) 0.0004(7) O5 0.0329(10) 0.0410(12) 0.0151(8) 0.0137(9) -0.0025(7) 0.0000(8) N1 0.0188(9) 0.0283(11) 0.0142(9) 0.0018(8) 0.0021(7) 0.0008(8) N2 0.0197(9) 0.0310(12) 0.0170(9) 0.0040(9) 0.0015(7) 0.0011(9) N3 0.0223(10) 0.0307(12) 0.0167(9) 0.0072(9) 0.0003(7) -0.0019(8) C1 0.0178(10) 0.0272(13) 0.0151(10) -0.0003(10) 0.0029(8) 0.0003(9) C2 0.0233(11) 0.0365(15) 0.0130(10) 0.0031(11) 0.0015(8) -0.0010(10) C4 0.0223(11) 0.0311(14) 0.0206(11) 0.0069(11) 0.0028(9) -0.0003(10) C3 0.0269(12) 0.0366(15) 0.0166(11) 0.0053(11) 0.0046(9) -0.0040(10) C5 0.0181(10) 0.0288(13) 0.0154(10) -0.0012(10) 0.0013(8) 0.0008(10) C6 0.0202(11) 0.0312(14) 0.0127(10) 0.0015(10) 0.0020(8) 0.0007(9) C7 0.0194(11) 0.0263(13) 0.0163(10) 0.0007(10) 0.0020(8) -0.0005(9) C8 0.0171(10) 0.0258(13) 0.0155(10) -0.0023(10) 0.0025(8) 0.0003(9) C9 0.0265(12) 0.0353(15) 0.0141(10) 0.0044(11) 0.0010(9) -0.0021(10) C10 0.0247(12) 0.0384(16) 0.0148(11) 0.0051(11) -0.0014(9) 0.0008(10) C11 0.0265(12) 0.0356(15) 0.0146(10) 0.0043(11) 0.0050(9) 0.0003(10) C12 0.0239(11) 0.0333(14) 0.0127(10) 0.0040(11) 0.0014(8) 0.0014(10) C13 0.0200(11) 0.0287(13) 0.0147(10) -0.0004(10) 0.0021(8) 0.0009(9) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag O1W H1WB 0.8200 ? O1W H1WA 0.8199 ? O1 C6 1.219(3) yes O2 C6 1.304(3) yes O3 C7 1.218(3) yes O4 C7 1.310(3) yes O5 C13 1.242(3) yes N1 C1 1.341(3) ? N1 C5 1.334(3) ? N2 C10 1.337(3) ? O2 H2O 0.8200 ? O4 H4O 0.8199 ? N2 C11 1.343(3) ? N3 C13 1.324(3) ? N3 H3NB 0.8700 ? N3 H3NA 0.8700 ? C1 C2 1.396(3) ? C1 C6 1.510(3) ? C2 C3 1.378(4) ? C2 H2A 0.9500 ? C4 C3 1.388(3) ? C4 C5 1.399(3) ? C4 H4A 0.9500 ? C3 H3A 0.9500 ? C5 C7 1.510(3) ? C8 C12 1.387(3) ? C8 C9 1.394(3) ? C8 C13 1.509(3) ? C9 C10 1.379(4) ? C9 H9A 0.9500 ? C10 H10A 0.9500 ? C11 C12 1.382(4) ? C11 H11A 0.9500 ? C12 H12A 0.9500 ? 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 H1WB O1W H1WA 116.8 ? C6 O2 H2O 114.4 ? C7 O4 H4O 106.1 ? C5 N1 C1 117.3(2) ? C10 N2 C11 118.2(2) ? C13 N3 H3NB 125.9 ? C13 N3 H3NA 119.3 ? H3NB N3 H3NA 114.6 ? N1 C1 C2 123.2(2) ? N1 C1 C6 115.5(2) ? C2 C1 C6 121.3(2) ? C3 C2 C1 118.7(2) ? C3 C2 H2A 120.6 ? C1 C2 H2A 120.6 ? C3 C4 C5 118.3(2) ? C3 C4 H4A 120.8 ? C5 C4 H4A 120.8 ? C2 C3 C4 118.9(2) ? C2 C3 H3A 120.5 ? C4 C3 H3A 120.5 ? N1 C5 C4 123.4(2) ? N1 C5 C7 115.3(2) ? C4 C5 C7 121.3(2) ? O1 C6 O2 124.2(2) yes O1 C6 C1 122.5(2) yes O2 C6 C1 113.3(2) yes O3 C7 O4 124.3(2) yes O3 C7 C5 122.0(2) yes O4 C7 C5 113.6(2) yes C12 C8 C9 117.9(2) ? C12 C8 C13 118.5(2) ? C9 C8 C13 123.6(2) ? C10 C9 C8 119.2(2) ? C10 C9 H9A 120.4 ? C8 C9 H9A 120.4 ? N2 C10 C9 122.8(2) ? N2 C10 H10A 118.6 ? C9 C10 H10A 118.6 ? N2 C11 C12 122.4(2) ? N2 C11 H11A 118.8 ? C12 C11 H11A 118.8 ? C11 C12 C8 119.5(2) ? C11 C12 H12A 120.3 ? C8 C12 H12A 120.3 ? O5 C13 N3 123.5(2) yes O5 C13 C8 118.6(2) yes N3 C13 C8 117.9(2) 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 _geom_torsion_publ_flag C5 N1 C1 C2 1.1(4) ? C5 N1 C1 C6 -179.3(2) ? N1 C1 C2 C3 -1.1(4) ? C6 C1 C2 C3 179.4(2) ? C1 C2 C3 C4 -0.1(4) ? C5 C4 C3 C2 1.0(4) ? C1 N1 C5 C4 -0.1(4) ? C1 N1 C5 C7 -179.4(2) ? C3 C4 C5 N1 -1.0(4) ? C3 C4 C5 C7 178.3(2) ? N1 C5 C7 O3 4.4(4) yes N1 C5 C7 O4 -176.2(2) yes N1 C1 C6 O1 0.9(4) yes C2 C1 C6 O1 -179.5(3) ? N1 C1 C6 O2 -179.7(2) yes C2 C1 C6 O2 -0.1(3) ? C4 C5 C7 O3 -174.9(2) ? C4 C5 C7 O4 4.5(3) ? C12 C8 C9 C10 -0.1(4) ? C13 C8 C9 C10 180.0(2) ? C11 N2 C10 C9 -1.5(4) ? C8 C9 C10 N2 1.1(4) ? C10 N2 C11 C12 1.0(4) ? N2 C11 C12 C8 -0.1(4) ? C9 C8 C12 C11 -0.4(4) ? C13 C8 C12 C11 179.6(2) ? C12 C8 C13 O5 4.2(4) yes C9 C8 C13 O5 -175.9(2) ? C12 C8 C13 N3 -175.6(2) yes C9 C8 C13 N3 4.4(4) ? 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 H4O O1W 2_555 0.82 1.75 2.559(3) 167 yes O2 H2O N2 3_646 0.82 1.76 2.574(3) 175 yes O1W H1WB O5 1_555 0.82 1.92 2.733(3) 170 yes N3 H3NA O3 1_555 0.87 2.04 2.905(3) 177 yes O1W H1WA O3 1_555 0.82 2.30 2.920(3) 132 yes N3 H3NB O1 1_555 0.87 2.07 2.934(3) 172 yes C9 H9A O1 1_555 0.95 2.34 3.264(3) 163 yes