#------------------------------------------------------------------------------
#$Date: 2016-02-20 02:53:41 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176768 $
#$URL: svn://www.crystallography.net/cod/cif/2/10/03/2100305.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_2100305
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 H3 D2 N O4'
_chemical_formula_sum            'C7 H3 D2 N O4'
_chemical_formula_weight         169.0
_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                 108.304(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.7614(13)
_cell_length_b                   11.2243(17)
_cell_length_c                   6.6430(13)
_cell_measurement_reflns_used    815
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      34.91
_cell_measurement_theta_min      3.63
_cell_volume                     691.0(2)
_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      296(2)
_diffrn_measured_fraction_theta_full 0.824
_diffrn_measured_fraction_theta_max 0.824
_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     0.84060(10)
_diffrn_reflns_av_R_equivalents  0.0141
_diffrn_reflns_av_sigmaI/netI    0.0468
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            1677
_diffrn_reflns_theta_full        34.85
_diffrn_reflns_theta_max         34.85
_diffrn_reflns_theta_min         3.37
_diffrn_standards_decay_%        none
_diffrn_standards_interval_count 50
_diffrn_standards_number         2
_exptl_absorpt_coefficient_mu    0.054
_exptl_absorpt_correction_T_max  0.9569
_exptl_absorpt_correction_T_min  0.9148
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   'DATAP, (Coppens, 1979)'
_exptl_crystal_colour            'pale brown'
_exptl_crystal_density_diffrn    1.610
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             255
_exptl_crystal_size_max          2.7
_exptl_crystal_size_mid          1.5
_exptl_crystal_size_min          0.9
_refine_diff_density_max         0.731
_refine_diff_density_min         -0.624
_refine_ls_extinction_coef       0.017(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.617
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     156
_refine_ls_number_reflns         1503
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.617
_refine_ls_R_factor_all          0.0967
_refine_ls_R_factor_gt           0.0738
_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)+(0.0500P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1456
_refine_ls_wR_factor_ref         0.1530
_reflns_number_gt                1182
_reflns_number_total             1503
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            bs5020.cif
_cod_data_source_block           dad
_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        691.02(19)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2100305
_cod_database_fobs_code          2100305
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 -0.3163(2) -0.33893(17) 0.2298(4) 0.0317(6) Uani d . 1 . . C
C3 -0.3879(2) -0.44272(16) 0.2521(4) 0.0276(5) Uani d . 1 . . C
C4 -0.3179(2) -0.55204(16) 0.2625(4) 0.0295(5) Uani d . 1 . . C
C5 -0.1791(2) -0.55423(17) 0.2452(4) 0.0289(5) Uani d . 1 . . C
C6 -0.1149(2) -0.44649(17) 0.2235(4) 0.0332(6) Uani d . 1 . . C
C7 -0.5384(2) -0.43893(18) 0.2647(4) 0.0293(5) Uani d . 1 . . C
C8 -0.0964(2) -0.66798(17) 0.2550(4) 0.0327(6) Uani d . 1 . . C
H1 -0.3653(16) -0.2517(10) 0.227(3) 0.049(3) Uani d P 0.20 . . D
H2 -0.3732(5) -0.6335(4) 0.2832(11) 0.0540(15) Uani d . 1 . . H
H3 -0.0081(14) -0.4433(12) 0.212(3) 0.056(4) Uani d P 0.20 . . D
D4 -0.6857(3) -0.3225(3) 0.2687(7) 0.0531(10) Uani d P 0.88 . . D
D5 0.0991(3) -0.7340(3) 0.2814(7) 0.0575(10) Uani d P 0.88 . . D
N1 -0.18269(16) -0.34204(13) 0.2142(3) 0.0372(5) Uani d . 1 . . N
O1 -0.5837(3) -0.3289(2) 0.2713(7) 0.0512(9) Uani d . 1 . . O
O2 -0.6091(3) -0.5270(2) 0.2646(5) 0.0375(7) Uani d . 1 . . O
O3 -0.1522(3) -0.7666(2) 0.2456(6) 0.0429(8) Uani d . 1 . . O
O4 0.0372(3) -0.6504(2) 0.2729(6) 0.0479(9) 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 0.0223(9) 0.0188(9) 0.0558(16) 0.0006(7) 0.0150(9) 0.0025(9)
C3 0.0197(8) 0.0184(9) 0.0474(15) 0.0021(6) 0.0142(8) 0.0008(9)
C4 0.0208(9) 0.0194(9) 0.0512(16) 0.0011(7) 0.0156(9) 0.0016(9)
C5 0.0191(8) 0.0187(9) 0.0509(15) 0.0022(6) 0.0138(8) 0.0007(9)
C6 0.0217(9) 0.0212(10) 0.0601(17) -0.0015(7) 0.0176(9) 0.0012(10)
C7 0.0199(8) 0.0237(9) 0.0467(14) 0.0016(7) 0.0139(8) 0.0030(9)
C8 0.0207(9) 0.0189(9) 0.0617(17) 0.0006(6) 0.0175(9) -0.0015(9)
H1 0.056(7) 0.023(5) 0.077(11) 0.003(5) 0.033(7) 0.007(6)
H2 0.040(2) 0.032(2) 0.099(5) -0.0027(18) 0.035(3) 0.000(3)
H3 0.031(6) 0.031(6) 0.113(15) -0.005(4) 0.030(7) 0.000(7)
D4 0.0285(13) 0.0364(15) 0.101(3) 0.0053(10) 0.0305(15) 0.0025(16)
D5 0.0335(14) 0.0510(18) 0.091(3) -0.0111(13) 0.0236(15) -0.0086(18)
N1 0.0240(7) 0.0190(7) 0.0728(14) -0.0021(5) 0.0213(7) 0.0017(7)
O1 0.0295(13) 0.0265(13) 0.106(3) 0.0058(9) 0.0334(15) 0.0034(15)
O2 0.0251(11) 0.0279(11) 0.063(2) -0.0041(9) 0.0186(12) -0.0003(12)
O3 0.0263(11) 0.0233(11) 0.084(2) 0.0004(9) 0.0244(13) 0.0019(13)
O4 0.0203(11) 0.0230(11) 0.102(3) 0.0030(9) 0.0215(14) -0.0050(14)
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'
D D '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
H1 C2 N1 117.1(7)
H1 C2 C3 121.6(7)
N1 C2 C3 121.33(17)
C2 C3 C4 119.18(16)
C2 C3 C7 121.11(16)
C4 C3 C7 119.71(16)
C5 C4 C3 118.97(16)
C5 C4 H2 121.8(3)
C3 C4 H2 119.2(3)
C6 C5 C4 118.31(16)
C6 C5 C8 119.36(15)
C4 C5 C8 122.31(16)
H3 C6 N1 116.5(7)
H3 C6 C5 121.2(7)
N1 C6 C5 122.31(16)
O2 C7 O1 124.8(2)
O2 C7 C3 123.2(2)
O1 C7 C3 111.95(18)
O3 C8 O4 124.3(2)
O3 C8 C5 122.77(18)
O4 C8 C5 112.91(18)
C6 N1 C2 119.88(15)
D4 O1 C7 114.4(3)
D5 O4 C8 113.3(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
C2 H1 . 1.087(12) ?
C2 N1 . 1.341(2) ?
C2 C3 . 1.390(3) ?
C3 C4 . 1.396(2) ?
C3 C7 . 1.498(2) ?
C4 C5 . 1.395(2) ?
C4 H2 . 1.092(5) ?
C5 C6 . 1.390(2) ?
C5 C8 . 1.501(3) ?
C6 H3 . 1.070(11) ?
C6 N1 . 1.338(2) ?
C7 O2 . 1.205(3) ?
C7 O1 . 1.317(3) ?
C8 O3 . 1.227(3) ?
C8 O4 . 1.286(3) ?
D4 O1 . 0.993(3) ?
D5 O4 . 1.108(4) ?
