#------------------------------------------------------------------------------
#$Date: 2017-10-13 07:28:26 +0200 (vie 13 de oct de 2017) $
#$Revision: 201972 $
#$URL: svn://www.crystallography.net/cod/cif/2/10/03/2100301.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_2100301
loop_
_publ_author_name
'Cowan, John. A.'
'Howard, Judith A. K.'
'McIntyre, Garry, J.'
'Lo, Samuel M.-F'
'Williams, Ian D.'
_publ_section_title
;
 Variable-temperature neutron diffraction studies of the short, strong
 hydrogen bonds in the crystal structure of pyridine-3,5-dicarboxylic
 acid
;
_journal_coeditor_code           BS5020
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section B'
_journal_page_first              724
_journal_page_last               730
_journal_paper_doi               10.1107/S0108768105030077
_journal_volume                  61
_journal_year                    2005
_chemical_formula_moiety         'C7 H5 N O4'
_chemical_formula_sum            'C7 H5 N O4'
_chemical_formula_weight         167.00
_chemical_name_common            'dinicotinic acid'
_chemical_name_systematic
;
 Pyridine-3,5-dicarboxylic acid
;
_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   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 108.595(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.7116(13)
_cell_length_b                   11.1347(17)
_cell_length_c                   6.4421(13)
_cell_measurement_reflns_used    510
_cell_measurement_temperature    15(2)
_cell_measurement_theta_max      35.06
_cell_measurement_theta_min      4.14
_cell_volume                     660.26(19)
_computing_cell_refinement       'RAFD9 (Filhol, 1998)'
_computing_data_collection       'MAD and HKLGEN (Barthelemy, 1984)'
_computing_data_reduction        'RACER (Wilkinson, et al. 1988)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      15(2)
_diffrn_measured_fraction_theta_full 0.886
_diffrn_measured_fraction_theta_max 0.886
_diffrn_measurement_device_type  D9
_diffrn_measurement_method       'theta - two theta scans'
_diffrn_radiation_monochromator  'Copper (2 2 0)'
_diffrn_radiation_probe          neutron
_diffrn_radiation_source         'ILL high flux reactor'
_diffrn_radiation_type           neutron
_diffrn_radiation_wavelength     0.84040(10)
_diffrn_reflns_av_R_equivalents  0.0174
_diffrn_reflns_av_sigmaI/netI    0.0707
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            1812
_diffrn_reflns_theta_full        35.93
_diffrn_reflns_theta_max         35.93
_diffrn_reflns_theta_min         4.33
_diffrn_standards_decay_%        none
_diffrn_standards_interval_count 50
_diffrn_standards_number         2
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_T_max  0.9812
_exptl_absorpt_correction_T_min  0.9064
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   'DATAP (Coppens, 1979)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.680
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             242
_exptl_crystal_size_max          1.7
_exptl_crystal_size_mid          1.5
_exptl_crystal_size_min          0.2
_refine_diff_density_max         1.195
_refine_diff_density_min         -0.969
_refine_ls_extinction_coef       0.0017(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.282
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     155
_refine_ls_number_reflns         1670
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.282
_refine_ls_R_factor_all          0.0814
_refine_ls_R_factor_gt           0.0601
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0200P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0930
_refine_ls_wR_factor_ref         0.0992
_reflns_number_gt                1335
_reflns_number_total             1670
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            bs5020.cif
_cod_data_source_block           pda15
_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_original_cell_volume        660.25(19)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2100301
_cod_database_fobs_code          2100301
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_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
C2 -0.31763(18) -0.34420(15) 0.2204(3) 0.0059(3) Uani d . 1 . . C
C3 -0.38927(17) -0.44817(13) 0.2512(3) 0.0039(3) Uani d . 1 . . C
C4 -0.31924(17) -0.55882(14) 0.2659(3) 0.0049(3) Uani d . 1 . . C
C5 -0.17975(16) -0.56379(14) 0.2482(3) 0.0042(3) Uani d . 1 . . C
C6 -0.11471(17) -0.45622(14) 0.2178(3) 0.0056(3) Uani d . 1 . . C
C7 -0.54046(17) -0.44232(14) 0.2647(3) 0.0041(3) Uani d . 1 . . C
C8 -0.09453(17) -0.67859(14) 0.2645(3) 0.0046(3) Uani d . 1 . . C
H1 -0.3661(4) -0.2548(3) 0.2097(7) 0.0190(8) Uani d . 1 . . H
H2 -0.3745(4) -0.6396(3) 0.2918(8) 0.0192(8) Uani d . 1 . . H
H3 -0.0055(4) -0.4526(3) 0.2066(8) 0.0202(8) Uani d . 1 . . H
H4 -0.6899(4) -0.3215(4) 0.2673(7) 0.0202(8) Uani d . 1 . . H
H5 0.1152(4) -0.7608(4) 0.3011(7) 0.0220(8) Uani d . 1 . . H
N1 -0.18382(13) -0.35111(10) 0.2044(2) 0.0059(2) Uani d . 1 . . N
O1 -0.5837(2) -0.33069(17) 0.2730(4) 0.0076(4) Uani d . 1 . . O
O2 -0.6118(2) -0.53203(17) 0.2659(4) 0.0070(4) Uani d . 1 . . O
O3 -0.1542(2) -0.77867(17) 0.2495(4) 0.0072(4) Uani d . 1 . . O
O4 0.0405(2) -0.66193(16) 0.2941(4) 0.0078(4) Uani d . 1 . . O
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
C2 0.0068(7) 0.0026(7) 0.0092(9) 0.0002(5) 0.0039(6) 0.0008(5)
C3 0.0042(7) 0.0018(7) 0.0064(8) 0.0001(5) 0.0030(6) -0.0007(5)
C4 0.0041(7) 0.0026(7) 0.0090(9) 0.0010(5) 0.0036(6) 0.0002(5)
C5 0.0027(7) 0.0028(7) 0.0078(8) 0.0003(5) 0.0026(6) 0.0009(5)
C6 0.0035(7) 0.0027(7) 0.0105(9) -0.0003(5) 0.0020(6) 0.0000(5)
C7 0.0030(6) 0.0033(7) 0.0063(8) 0.0014(5) 0.0019(6) 0.0000(5)
C8 0.0032(7) 0.0019(7) 0.0089(9) 0.0003(5) 0.0023(6) 0.0005(5)
H1 0.0184(17) 0.0087(15) 0.033(2) 0.0049(12) 0.0133(15) 0.0036(14)
H2 0.0163(16) 0.0114(16) 0.031(2) -0.0032(12) 0.0096(16) 0.0012(14)
H3 0.0137(16) 0.0150(16) 0.034(2) 0.0023(12) 0.0110(15) 0.0022(14)
H4 0.0148(17) 0.0205(18) 0.027(2) 0.0008(13) 0.0095(15) 0.0012(14)
H5 0.0201(17) 0.0202(18) 0.026(2) -0.0047(14) 0.0083(16) -0.0010(15)
N1 0.0051(5) 0.0030(5) 0.0100(6) -0.0007(4) 0.0031(4) -0.0003(4)
O1 0.0053(8) 0.0056(8) 0.0127(11) 0.0009(6) 0.0040(7) 0.0001(7)
O2 0.0064(8) 0.0039(8) 0.0116(10) -0.0012(6) 0.0040(7) -0.0002(7)
O3 0.0053(7) 0.0046(8) 0.0121(10) -0.0014(6) 0.0032(7) 0.0001(7)
O4 0.0047(8) 0.0041(8) 0.0141(10) 0.0002(6) 0.0023(7) -0.0004(7)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_source
C C 'V.F. Sears, Neutron News, Vol. 3, 1992'
H H 'V.F. Sears, Neutron News, Vol. 3, 1992'
N N 'V.F. Sears, Neutron News, Vol. 3, 1992'
O O 'V.F. Sears, Neutron News, Vol. 3, 1992'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
N1 C2 C3 120.21(14)
N1 C2 H1 117.2(2)
C3 C2 H1 122.6(2)
C4 C3 C2 119.15(14)
C4 C3 C7 119.95(14)
C2 C3 C7 120.89(14)
C3 C4 C5 119.60(14)
C3 C4 H2 119.1(2)
C5 C4 H2 121.3(2)
C4 C5 C6 118.12(14)
C4 C5 C8 123.57(14)
C6 C5 C8 118.29(13)
N1 C6 C5 121.27(14)
N1 C6 H3 116.3(2)
C5 C6 H3 122.4(2)
O2 C7 O1 125.75(18)
O2 C7 C3 122.30(16)
O1 C7 C3 111.95(14)
O3 C8 O4 124.85(17)
O3 C8 C5 121.45(16)
O4 C8 C5 113.69(15)
C6 N1 C2 121.66(13)
C7 O1 H4 115.0(3)
C8 O4 H5 114.4(2)
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
C2 N1 . 1.338(2) ?
C2 C3 . 1.397(2) ?
C2 H1 . 1.094(4) ?
C3 C4 . 1.396(2) ?
C3 C7 . 1.500(2) ?
C4 C5 . 1.396(2) ?
C4 H2 . 1.087(4) ?
C5 C6 . 1.397(2) ?
C5 C8 . 1.508(2) ?
C6 N1 . 1.3381(19) ?
C6 H3 . 1.086(4) ?
C7 O2 . 1.217(2) ?
C7 O1 . 1.319(2) ?
C8 O3 . 1.245(2) ?
C8 O4 . 1.277(2) ?
O1 H4 . 1.025(4) ?
O4 H5 . 1.311(5) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 9939
