#------------------------------------------------------------------------------ #$Date: 2013-12-28 15:58:47 +0200 (Sat, 28 Dec 2013) $ #$Revision: 91933 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/01/26/2012650.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_2012650 loop_ _publ_author_name 'Carranza T\'ellez, Vladimir' 'S\'anchez Gayt\'an, Brenda' 'Bern\`es, Sylvain' 'Gonz\'alez Vergara, Enrique' _publ_section_title ; The supramolecular structure of pyridine-2,6-dicarboxylic acid ; _journal_issue 4 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first o228 _journal_page_last o230 _journal_volume 58 _journal_year 2002 _chemical_formula_moiety 'C7 H5 N O4' _chemical_formula_sum 'C7 H5 N O4' _chemical_formula_weight 167.12 _chemical_melting_point 525 _chemical_name_common 'Dipicolinic acid' _chemical_name_systematic '2,6-pyridinedicarboxylic acid' _space_group_IT_number 11 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2yb' _symmetry_space_group_name_H-M 'P 1 21/m 1' _atom_sites_solution_hydrogens difmap _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL97 _cell_angle_alpha 90 _cell_angle_beta 93.156(7) _cell_angle_gamma 90 _cell_formula_units_Z 2 _cell_length_a 3.7663(6) _cell_length_b 16.1667(12) _cell_length_c 5.5705(4) _cell_measurement_reflns_used 70 _cell_measurement_temperature 300(2) _cell_measurement_theta_max 18.39 _cell_measurement_theta_min 3.86 _cell_volume 338.67(6) _computing_cell_refinement XSCANS _computing_data_collection 'XSCANS (Siemens, 1996)' _computing_data_reduction XSCANS _computing_molecular_graphics 'SHELXTL (Bruker, 1997)' _computing_publication_material SHELXL97 _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _diffrn_ambient_temperature 300(2) _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measurement_device_type 'Bruker P4' _diffrn_measurement_method \w _diffrn_radiation_monochromator graphite _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.036 _diffrn_reflns_av_sigmaI/netI 0.023 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_l_max 7 _diffrn_reflns_limit_l_min -7 _diffrn_reflns_number 3920 _diffrn_reflns_theta_full 29.99 _diffrn_reflns_theta_max 29.99 _diffrn_reflns_theta_min 2.52 _diffrn_standards_decay_% 1 _diffrn_standards_interval_count 97 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu 0.138 _exptl_absorpt_correction_type none _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.639 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_method 'not measured' _exptl_crystal_description irregular _exptl_crystal_F_000 172 _exptl_crystal_size_max 0.7 _exptl_crystal_size_mid 0.4 _exptl_crystal_size_min 0.4 _refine_diff_density_max 0.34 _refine_diff_density_min -0.18 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.061 _refine_ls_hydrogen_treatment refall _refine_ls_matrix_type full _refine_ls_number_parameters 74 _refine_ls_number_reflns 1021 _refine_ls_number_restraints 2 _refine_ls_restrained_S_all 1.060 _refine_ls_R_factor_all 0.043 _refine_ls_R_factor_gt 0.040 _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^)+(0.0827P)^2^+0.0236P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.118 _refine_ls_wR_factor_ref 0.121 _reflns_number_gt 937 _reflns_number_total 1021 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file sk1531.cif _[local]_cod_data_source_block I _[local]_cod_cif_authors_sg_H-M 'P 21/m' _[local]_cod_cif_authors_sg_Hall -P2yb _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 ; _cod_database_code 2012650 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' '-x, -y, -z' 'x, -y-1/2, z' 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 C1 0.1489(2) 0.60137(5) 0.64848(17) 0.0331(2) Uani d . 1 . . C C2 0.2615(2) 0.67993(5) 0.77301(14) 0.0287(2) Uani d . 1 . . C C3 0.4513(3) 0.67632(5) 0.99546(17) 0.0337(2) Uani d . 1 . . C H3 0.516(4) 0.6252(12) 1.070(3) 0.049(4) Uiso d . 1 . . H C4 0.5489(3) 0.7500 1.1093(2) 0.0349(3) Uani d S 1 . . C H4 0.698(7) 0.7500 1.272(5) 0.063(7) Uiso d S 1 . . H N1 0.1650(3) 0.7500 0.66094(18) 0.0289(2) Uani d S 1 . . N O1 0.2503(3) 0.53435(5) 0.75157(16) 0.0580(3) Uani d D 1 . . O H1 0.158(7) 0.4969(19) 0.688(5) 0.054(6) Uiso d PD 0.66(3) . . H O2 -0.0354(2) 0.60406(4) 0.45566(14) 0.0490(3) Uani d D 1 . . O H2 -0.119(12) 0.564(2) 0.401(8) 0.054(6) Uiso d PD 0.34(3) . . H 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 C1 0.0399(4) 0.0239(4) 0.0346(4) -0.0008(3) -0.0070(3) 0.0025(3) C2 0.0329(4) 0.0239(4) 0.0287(4) 0.0000(2) -0.0039(3) 0.0012(2) C3 0.0384(4) 0.0318(5) 0.0300(4) 0.0012(3) -0.0058(3) 0.0044(3) C4 0.0393(6) 0.0381(6) 0.0264(5) 0.000 -0.0069(4) 0.000 N1 0.0345(5) 0.0235(4) 0.0281(4) 0.000 -0.0050(3) 0.000 O1 0.0862(6) 0.0237(4) 0.0600(5) -0.0001(3) -0.0339(5) 0.0061(3) O2 0.0722(6) 0.0272(4) 0.0444(5) -0.0014(3) -0.0262(4) -0.0003(3) 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 C1 O1 . 1.2750(10) y C1 O2 . 1.2472(12) y C1 C2 . 1.4973(11) y C2 N1 . 1.3342(9) y C2 C3 . 1.3973(12) y C3 C4 . 1.3894(11) y C3 H3 . 0.95(2) y C4 C3 4_575 1.3894(11) n C4 H4 . 1.04(3) y N1 C2 4_575 1.3342(9) n O1 H1 . 0.77(3) y O2 H2 . 0.77(3) y 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_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l 0 -4 1 2 -6 2 -1 7 -3 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 O2 C1 O1 . . 123.81(9) y O2 C1 C2 . . 119.96(8) y O1 C1 C2 . . 116.23(8) y N1 C2 C3 . . 124.29(8) y N1 C2 C1 . . 116.14(8) y C3 C2 C1 . . 119.57(7) y C4 C3 C2 . . 118.58(8) y C4 C3 H3 . . 119.4(11) y C2 C3 H3 . . 122.0(11) y C3 C4 C3 . 4_575 118.04(12) y C3 C4 H4 . . 120.96(6) y C3 C4 H4 4_575 . 120.96(8) n C2 N1 C2 4_575 . 116.22(10) y C1 O1 H1 . . 110(2) y C1 O2 H2 . . 120(4) y 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 O1 H1 O2 3_566 0.77(3) 1.86(3) 2.6252(12) 167(3) y O2 H2 O1 3_566 0.77(3) 1.86(3) 2.6252(12) 171(5) 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_site_symmetry_4 _geom_torsion _geom_torsion_publ_flag O2 C1 C2 N1 . -2.51(15) n O1 C1 C2 N1 . 177.88(9) n O2 C1 C2 C3 . 176.50(9) n O1 C1 C2 C3 . -3.11(14) n N1 C2 C3 C4 . -0.23(17) n C1 C2 C3 C4 . -179.16(8) n C2 C3 C4 C3 4_575 0.16(19) n C3 C2 N1 C2 4_575 0.28(17) n C1 C2 N1 C2 4_575 179.24(6) n O2 C1 C2 N1 . -2.51(15) n O1 C1 C2 N1 . 177.88(9) n O2 C1 C2 C3 . 176.50(9) n O1 C1 C2 C3 . -3.11(14) n N1 C2 C3 C4 . -0.23(17) n C1 C2 C3 C4 . -179.16(8) n C2 C3 C4 C3 4_575 0.16(19) n C3 C2 N1 C2 4_575 0.28(17) n C1 C2 N1 C2 4_575 179.24(6) n H4 C4 C3 H3 . 2.0(17) n H4 C4 C3 C2 . -177.8(15) n H3 C3 C2 C1 . 1.1(10) n H3 C3 C2 N1 . 180.0(10) n H1 O1 C1 O2 . -9(2) n H1 O1 C1 C2 . 171(2) n H2 O2 C1 O1 . 9(4) n H2 O2 C1 C2 . -170(4) n _cod_database_fobs_code 2012650 _journal_paper_doi 10.1107/S0108270102002172