#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:48:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201957 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/74/2017487.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_2017487
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 -'
_chemical_formula_moiety         'C6 H6 N O2 + , C4 H5 O6 -'
_chemical_formula_sum            'C10 H11 N O8'
_chemical_formula_weight         273.20
_chemical_melting_point_gt       470
_chemical_melting_point_lt       471
_chemical_name_common            'nicotinic acid hydrogen L-tartrate'
_chemical_name_systematic
;
3-carboxypyridinium hydrogen (2R,3R)-tartrate
;
_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                   6.5792(2)
_cell_length_b                   7.7637(2)
_cell_length_c                   21.6830(5)
_cell_measurement_reflns_used    3162
_cell_measurement_temperature    297(2)
_cell_measurement_theta_max      28.54
_cell_measurement_theta_min      3.22
_cell_volume                     1107.54(5)
_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 0.996
_diffrn_measured_fraction_theta_max 0.919
_diffrn_measurement_device_type  'Oxford Gemini-S Ultra 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  0.0202
_diffrn_reflns_av_sigmaI/netI    0.0234
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            5552
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         28.65
_diffrn_reflns_theta_min         3.23
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.145
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.638
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.156
_refine_diff_density_min         -0.163
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         1537
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.0377
_refine_ls_R_factor_gt           0.0294
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0397P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0644
_refine_ls_wR_factor_ref         0.0662
_reflns_number_gt                1317
_reflns_number_total             1537
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            sf3121.cif
_cod_data_source_block           II
_cod_original_cell_volume        1107.55(5)
_cod_database_code               2017487
_cod_database_fobs_code          2017487
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 0.6742(2) 0.15971(17) 0.03744(6) 0.0376(5) Uani . . 1.000
O O12 0.7555(2) 0.22385(16) 0.13467(6) 0.0408(5) Uani . . 1.000
O O21 0.9124(2) 0.52781(17) 0.09742(6) 0.0294(4) Uani . . 1.000
O O31 0.4801(2) 0.53849(18) 0.10680(6) 0.0311(4) Uani . . 1.000
O O41 0.6248(2) 0.84011(15) 0.06913(5) 0.0349(5) Uani . . 1.000
O O42 0.66173(19) 0.75197(15) -0.02806(5) 0.0286(4) Uani . . 1.000
C C11 0.7361(3) 0.2634(2) 0.08147(8) 0.0258(5) Uani . . 1.000
C C21 0.7797(3) 0.4425(2) 0.05612(7) 0.0236(5) Uani . . 1.000
C C31 0.5792(3) 0.5418(2) 0.04895(8) 0.0241(5) Uani . . 1.000
C C41 0.6244(3) 0.7273(2) 0.02875(8) 0.0229(5) Uani . . 1.000
O O71 0.7577(3) 0.31198(16) 0.32594(6) 0.0493(6) Uani . . 1.000
O O72 0.8220(3) 0.50398(17) 0.39924(6) 0.0441(5) Uani . . 1.000
N N1 0.7280(3) 0.7089(2) 0.19859(7) 0.0460(6) Uani . . 1.000
C C2 0.7403(4) 0.5767(2) 0.23779(9) 0.0395(6) Uani . . 1.000
C C3 0.7689(3) 0.6084(2) 0.29942(7) 0.0262(5) Uani . . 1.000
C C4 0.7844(3) 0.7769(2) 0.31907(8) 0.0311(6) Uani . . 1.000
C C5 0.7702(3) 0.9095(2) 0.27691(8) 0.0370(6) Uani . . 1.000
C C6 0.7419(3) 0.8722(2) 0.21607(8) 0.0382(7) Uani . . 1.000
C C7 0.7825(3) 0.4584(2) 0.34307(8) 0.0305(5) Uani . . 1.000
H H11 0.648(4) 0.052(4) 0.0516(12) 0.074(8) Uiso . . 1.000
H H21 0.84560 0.43210 0.01580 0.0280 Uiso calc R 1.000
H H21A 0.992(5) 0.600(4) 0.0762(11) 0.068(8) Uiso . . 1.000
H H31 0.49390 0.48510 0.01790 0.0290 Uiso calc R 1.000
H H31A 0.386(5) 0.617(4) 0.1071(13) 0.077(9) Uiso . . 1.000
H H1 0.694(4) 0.687(3) 0.1598(13) 0.061(8) Uiso . . 1.000
H H2 0.72950 0.46420 0.22340 0.0470 Uiso calc R 1.000
H H4 0.80440 0.80100 0.36060 0.0370 Uiso calc R 1.000
H H5 0.77990 1.02340 0.28990 0.0440 Uiso calc R 1.000
H H6 0.73240 0.96030 0.18710 0.0460 Uiso calc R 1.000
H H72 0.825(5) 0.402(4) 0.4263(11) 0.080(9) 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 . . . 112.2(17) no
C21 O21 H21A . . . 109.2(17) no
C31 O31 H31A . . . 108.8(19) no
C7 O72 H72 . . . 110.2(16) no
C2 N1 C6 . . . 123.28(16) no
C2 N1 H1 . . . 118.2(15) no
C6 N1 H1 . . . 118.1(15) no
O12 C11 C21 . . . 124.09(15) no
O11 C11 O12 . . . 125.07(15) no
O11 C11 C21 . . . 110.84(14) no
O21 C21 C31 . . . 111.04(13) no
C11 C21 C31 . . . 109.46(15) no
O21 C21 C11 . . . 108.37(13) no
C21 C31 C41 . . . 109.49(15) no
O31 C31 C21 . . . 107.29(13) no
O31 C31 C41 . . . 111.08(14) no
O41 C41 O42 . . . 125.34(15) no
O41 C41 C31 . . . 117.54(15) no
O42 C41 C31 . . . 117.11(14) no
C11 C21 H21 . . . 109.00 no
O21 C21 H21 . . . 109.00 no
C31 C21 H21 . . . 109.00 no
C41 C31 H31 . . . 110.00 no
O31 C31 H31 . . . 110.00 no
C21 C31 H31 . . . 110.00 no
N1 C2 C3 . . . 119.38(15) no
C2 C3 C4 . . . 118.76(15) no
C2 C3 C7 . . . 118.85(14) no
C4 C3 C7 . . . 122.39(14) no
C3 C4 C5 . . . 119.86(16) no
C4 C5 C6 . . . 119.46(15) no
N1 C6 C5 . . . 119.27(15) no
O71 C7 O72 . . . 125.03(16) no
O71 C7 C3 . . . 121.86(16) no
O72 C7 C3 . . . 113.11(14) no
N1 C2 H2 . . . 120.00 no
C3 C2 H2 . . . 120.00 no
C3 C4 H4 . . . 120.00 no
C5 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 . . 1.314(2) no
O12 C11 . . 1.201(2) no
O21 C21 . . 1.415(2) no
O31 C31 . . 1.414(2) no
O41 C41 . . 1.238(2) no
O42 C41 . . 1.271(2) no
O11 H11 . . 0.91(3) no
O21 H21A . . 0.89(3) no
O31 H31A . . 0.87(3) no
O71 C7 . . 1.207(2) no
O72 C7 . . 1.295(2) no
O72 H72 . . 0.99(3) no
N1 C2 . . 1.335(2) no
N1 C6 . . 1.326(2) no
N1 H1 . . 0.89(3) no
C11 C21 . . 1.522(2) no
C21 C31 . . 1.536(3) no
C31 C41 . . 1.534(2) no
C21 H21 . . 0.9800 no
C31 H31 . . 0.9800 no
C2 C3 . . 1.372(2) no
C3 C4 . . 1.380(2) no
C3 C7 . . 1.503(2) no
C4 C5 . . 1.380(2) no
C5 C6 . . 1.363(2) no
C2 H2 . . 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 O21 . 0.89(3) 2.33(3) 2.874(2) 120(2) yes
N1 H1 O31 . 0.89(3) 2.15(3) 2.893(2) 141(2) yes
N1 H1 O41 . 0.89(3) 2.34(3) 3.0624(19) 138(2) yes
O11 H11 O41 1_545 0.91(3) 1.70(3) 2.5951(18) 171(3) yes
O21 H21A O42 3_565 0.89(3) 1.91(3) 2.8064(18) 178(3) yes
O31 H31A O42 3_465 0.87(3) 2.48(3) 3.1542(18) 135(2) yes
O31 H31A O71 4_655 0.87(3) 2.30(3) 3.014(2) 139(2) yes
O72 H72 O42 2_665 0.99(3) 1.55(3) 2.5387(17) 176.3(19) yes
C5 H5 O71 1_565 0.93 2.38 3.302(2) 172 no
C6 H6 O12 1_565 0.93 2.35 3.252(2) 165 no
C21 H21 O11 3_555 0.98 2.55 3.389(2) 143 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 . . . . 0.0(3) no
C6 N1 C2 C3 . . . . -0.1(4) no
O11 C11 C21 O21 . . . . -158.61(15) no
O12 C11 C21 C31 . . . . -99.6(2) no
O12 C11 C21 O21 . . . . 21.6(3) no
O11 C11 C21 C31 . . . . 80.15(18) no
O21 C21 C31 O31 . . . . -65.11(17) no
C11 C21 C31 O31 . . . . 54.50(17) no
C11 C21 C31 C41 . . . . 175.14(13) no
O21 C21 C31 C41 . . . . 55.53(17) no
C21 C31 C41 O41 . . . . -98.77(19) no
C21 C31 C41 O42 . . . . 80.1(2) no
O31 C31 C41 O42 . . . . -161.59(16) no
O31 C31 C41 O41 . . . . 19.5(2) no
N1 C2 C3 C7 . . . . -180.0(2) no
N1 C2 C3 C4 . . . . -0.1(3) no
C2 C3 C4 C5 . . . . 0.3(3) no
C2 C3 C7 O71 . . . . -4.2(3) no
C2 C3 C7 O72 . . . . 176.0(2) no
C4 C3 C7 O71 . . . . 175.9(2) no
C4 C3 C7 O72 . . . . -3.9(3) no
C7 C3 C4 C5 . . . . -179.82(19) no
C3 C4 C5 C6 . . . . -0.3(3) no
C4 C5 C6 N1 . . . . 0.2(3) no
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30654212
