#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:48:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201957 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/74/2017488.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_2017488
loop_
_publ_author_name
'Smith, Graham'
'Wermuth, Urs D.'
_publ_section_title
;
 Three-dimensional hydrogen-bonded structures in the 1:1
 proton-transfer compounds of <small>L</small>-tartaric acid with the
 associative-group monosubstituted pyridines 3-aminopyridine,
 3-carboxypyridine (nicotinic acid) and 2-carboxypyridine (picolinic
 acid)
;
_journal_coeditor_code           SF3121
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o5
_journal_page_last               o10
_journal_paper_doi               10.1107/S0108270109049154
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C6 H6 N O2 + , C4 H5 O6 - , H2 O'
_chemical_formula_moiety         'C6 H6 N O2 + , C4 H5 O6 - , H2 O'
_chemical_formula_sum            'C10 H13 N O9'
_chemical_formula_weight         291.21
_chemical_melting_point          393
_chemical_name_common
'picolinic acid hydrogen L-tartrate monohydrate'
_chemical_name_systematic
;
2-carboxypyridinium hydrogen (2R,3R)-tartrate monohydrate
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.1536(4)
_cell_length_b                   7.8273(3)
_cell_length_c                   22.0145(10)
_cell_measurement_reflns_used    2870
_cell_measurement_temperature    297(2)
_cell_measurement_theta_max      32.51
_cell_measurement_theta_min      2.98
_cell_volume                     1232.67(10)
_computing_cell_refinement       'CrysAlis RED (Oxford Diffraction, 2008)'
_computing_data_collection       'CrysAlis CCD (Oxford Diffraction, 2008)'
_computing_data_reduction        'CrysAlis RED (Oxford Diffraction, 2008)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'PLATON (Spek, 2009)'
_computing_structure_refinement
;
SHELXL97 (Sheldrick, 2008) within WinGX (Farrugia, 1999)
;
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      297(2)
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'Oxford Gemini-S CCD area-detector'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Mo) X-ray source'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0510
_diffrn_reflns_av_sigmaI/netI    0.0433
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            6582
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         27.99
_diffrn_reflns_theta_min         2.99
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.141
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.569
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.273
_refine_diff_density_min         -0.240
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         1709
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0608
_refine_ls_R_factor_gt           0.0470
_refine_ls_shift/su_max          0.018
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0570P)²+0.2031P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1021
_refine_ls_wR_factor_ref         0.1067
_reflns_number_gt                1416
_reflns_number_total             1709
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            sf3121.cif
_cod_data_source_block           III
_cod_database_code               2017488
_cod_database_fobs_code          2017488
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 1/2-x,-y,1/2+z
3 1/2+x,1/2-y,-z
4 -x,1/2+y,1/2-z
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_thermal_displace_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
O O11 0.3506(5) 0.2113(3) 0.63764(11) 0.0563(8) Uani . . 1.000
O O12 0.2088(4) 0.1846(3) 0.72684(11) 0.0532(8) Uani . . 1.000
O O21 0.1116(3) -0.1453(3) 0.70206(10) 0.0327(6) Uani . . 1.000
O O31 0.5010(3) -0.1538(3) 0.70280(12) 0.0431(8) Uani . . 1.000
O O41 0.3902(4) -0.4548(3) 0.65870(10) 0.0433(7) Uani . . 1.000
O O42 0.2845(4) -0.3362(3) 0.57279(9) 0.0477(8) Uani . . 1.000
C C11 0.2563(4) 0.1275(3) 0.67903(12) 0.0289(8) Uani . . 1.000
C C21 0.2164(4) -0.0553(3) 0.65868(11) 0.0257(7) Uani . . 1.000
C C31 0.3973(4) -0.1523(3) 0.64838(12) 0.0270(8) Uani . . 1.000
C C41 0.3542(4) -0.3322(3) 0.62556(13) 0.0291(8) Uani . . 1.000
O O71 0.7952(5) -0.0020(2) 0.56837(10) 0.0609(8) Uani . . 1.000
O O72 0.7516(5) 0.1131(3) 0.47707(10) 0.0629(11) Uani . . 1.000
N N1 0.8059(4) 0.3089(3) 0.61942(11) 0.0321(7) Uani . . 1.000
C C2 0.7895(5) 0.2960(3) 0.55920(13) 0.0317(8) Uani . . 1.000
C C3 0.7882(6) 0.4413(4) 0.52454(14) 0.0450(9) Uani . . 1.000
C C4 0.8085(7) 0.5978(4) 0.55221(15) 0.0494(12) Uani . . 1.000
C C5 0.8294(5) 0.6058(4) 0.61403(16) 0.0440(10) Uani . . 1.000
C C6 0.8250(5) 0.4589(4) 0.64728(14) 0.0404(10) Uani . . 1.000
C C7 0.7787(5) 0.1169(3) 0.53434(12) 0.0356(9) Uani . . 1.000
O O1W 0.8011(4) 0.0703(3) 0.71291(10) 0.0367(7) Uani . . 1.000
H H11 0.354(6) 0.316(6) 0.6469(19) 0.063(13) Uiso . . 1.000
H H21 0.14610 -0.05200 0.62050 0.0310 Uiso calc R 1.000
H H21A 0.016(5) -0.093(5) 0.7065(15) 0.047(10) Uiso . . 1.000
H H31 0.47020 -0.09240 0.61730 0.0320 Uiso calc R 1.000
H H31A 0.510(7) -0.245(6) 0.7111(19) 0.067(15) Uiso . . 1.000
H H1 0.803(6) 0.220(5) 0.6417(17) 0.054(11) Uiso . . 1.000
H H3 0.77380 0.43420 0.48260 0.0540 Uiso calc R 1.000
H H4 0.80800 0.69740 0.52920 0.0590 Uiso calc R 1.000
H H5 0.84630 0.71060 0.63320 0.0530 Uiso calc R 1.000
H H6 0.83540 0.46340 0.68940 0.0490 Uiso calc R 1.000
H H72 0.765(9) 0.005(7) 0.459(2) 0.100(16) Uiso . . 1.000
H H11W 0.705(7) -0.002(6) 0.7157(17) 0.068(13) Uiso . . 1.000
H H12W 0.826(7) 0.122(6) 0.744(2) 0.079(16) Uiso . . 1.000
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_
_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_2
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C11 O11 H11 . . . 109(3) no
C21 O21 H21A . . . 106(3) no
C31 O31 H31A . . . 105(3) no
C7 O72 H72 . . . 115(3) no
H11W O1W H12W . . . 115(4) no
C2 N1 C6 . . . 122.2(2) no
C2 N1 H1 . . . 121(3) no
C6 N1 H1 . . . 117(3) no
O11 C11 O12 . . . 125.0(3) no
O12 C11 C21 . . . 123.9(2) no
O11 C11 C21 . . . 111.2(2) no
C11 C21 C31 . . . 110.7(2) no
O21 C21 C31 . . . 107.8(2) no
O21 C21 C11 . . . 111.8(2) no
O31 C31 C41 . . . 112.2(2) no
C21 C31 C41 . . . 109.8(2) no
O31 C31 C21 . . . 109.0(2) no
O41 C41 O42 . . . 127.4(3) no
O41 C41 C31 . . . 118.8(3) no
O42 C41 C31 . . . 113.9(2) no
O21 C21 H21 . . . 109.00 no
C11 C21 H21 . . . 109.00 no
C31 C21 H21 . . . 109.00 no
C41 C31 H31 . . . 109.00 no
O31 C31 H31 . . . 109.00 no
C21 C31 H31 . . . 109.00 no
N1 C2 C7 . . . 115.8(2) no
C3 C2 C7 . . . 124.7(3) no
N1 C2 C3 . . . 119.4(2) no
C2 C3 C4 . . . 119.5(3) no
C3 C4 C5 . . . 119.5(3) no
C4 C5 C6 . . . 119.5(3) no
N1 C6 C5 . . . 119.9(3) no
O71 C7 C2 . . . 119.3(2) no
O72 C7 C2 . . . 112.9(2) no
O71 C7 O72 . . . 127.8(2) no
C2 C3 H3 . . . 120.00 no
C4 C3 H3 . . . 120.00 no
C5 C4 H4 . . . 120.00 no
C3 C4 H4 . . . 120.00 no
C4 C5 H5 . . . 120.00 no
C6 C5 H5 . . . 120.00 no
N1 C6 H6 . . . 120.00 no
C5 C6 H6 . . . 120.00 no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O11 C11 . . 1.310(4) no
O12 C11 . . 1.193(4) no
O21 C21 . . 1.404(3) no
O31 C31 . . 1.409(4) no
O41 C41 . . 1.233(3) no
O42 C41 . . 1.265(4) no
O11 H11 . . 0.85(5) no
O21 H21A . . 0.80(4) no
O31 H31A . . 0.74(5) no
O71 C7 . . 1.201(3) no
O72 C7 . . 1.276(3) no
O72 H72 . . 0.94(5) no
O1W H12W . . 0.82(5) no
O1W H11W . . 0.89(5) no
N1 C6 . . 1.332(4) no
N1 C2 . . 1.335(4) no
N1 H1 . . 0.85(4) no
C11 C21 . . 1.526(3) no
C21 C31 . . 1.517(4) no
C31 C41 . . 1.527(3) no
C21 H21 . . 0.9800 no
C31 H31 . . 0.9800 no
C2 C7 . . 1.507(3) no
C2 C3 . . 1.370(4) no
C3 C4 . . 1.376(4) no
C4 C5 . . 1.371(5) no
C5 C6 . . 1.363(5) no
C3 H3 . . 0.9300 no
C4 H4 . . 0.9300 no
C5 H5 . . 0.9300 no
C6 H6 . . 0.9300 no
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
N1 H1 O1W . 0.85(4) 1.96(4) 2.779(3) 162(4) yes
N1 H1 O71 . 0.85(4) 2.37(4) 2.682(3) 102(3) yes
O11 H11 O41 1_565 0.85(5) 1.83(5) 2.669(3) 171(4) yes
O21 H21A O1W 1_455 0.80(4) 2.00(4) 2.800(3) 171(4) yes
O31 H31A O41 . 0.74(5) 2.18(5) 2.669(3) 124(4) yes
O31 H31A O12 4_646 0.74(5) 2.49(5) 2.883(4) 115(4) yes
O72 H72 O42 3_546 0.94(5) 1.50(5) 2.441(3) 177(6) yes
O1W H11W O31 . 0.89(5) 1.90(5) 2.781(3) 168(4) yes
O1W H12W O21 4_656 0.82(5) 2.22(5) 2.975(3) 154(4) yes
C4 H4 O71 1_565 0.93 2.51 3.154(4) 127 no
C4 H4 O42 3_556 0.93 2.50 3.329(4) 149 no
C6 H6 O12 4_656 0.93 2.55 3.295(4) 137 no
C6 H6 O21 4_656 0.93 2.56 3.446(4) 158 no
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
C2 N1 C6 C5 . . . . -0.4(5) no
C6 N1 C2 C3 . . . . -1.4(5) no
C6 N1 C2 C7 . . . . 177.0(3) no
O11 C11 C21 C31 . . . . 61.2(3) no
O11 C11 C21 O21 . . . . -178.6(3) no
O12 C11 C21 O21 . . . . 2.2(4) no
O12 C11 C21 C31 . . . . -118.1(3) no
O21 C21 C31 O31 . . . . -63.5(3) no
C11 C21 C31 C41 . . . . -177.7(2) no
O21 C21 C31 C41 . . . . 59.8(3) no
C11 C21 C31 O31 . . . . 59.0(3) no
O31 C31 C41 O41 . . . . 8.9(4) no
O31 C31 C41 O42 . . . . -170.7(3) no
C21 C31 C41 O41 . . . . -112.6(3) no
C21 C31 C41 O42 . . . . 67.9(3) no
N1 C2 C3 C4 . . . . 1.6(6) no
C7 C2 C3 C4 . . . . -176.7(4) no
N1 C2 C7 O71 . . . . -4.0(5) no
N1 C2 C7 O72 . . . . 175.9(3) no
C3 C2 C7 O71 . . . . 174.4(4) no
C3 C2 C7 O72 . . . . -5.7(5) no
C2 C3 C4 C5 . . . . -0.1(7) no
C3 C4 C5 C6 . . . . -1.7(6) no
C4 C5 C6 N1 . . . . 1.9(6) no
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30654213
