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)
Smith, Graham; Wermuth, Urs D.; Acta Crystallographica Section C 66 (2010) o5–o10; doi:10.1107/S0108270109049154

data_2017488
_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 (2<i>R</i>,3<i>R</i>)-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 <i>et al.</i>, 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       \w
_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/[\s^2^(Fo^2^)+(0.0570P)^2^+0.2031P] where P=(Fo^2^+2Fc^2^)/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>2\s(I)
_cod_data_source_file            sf3121.cif
_cod_data_source_block           III
_cod_database_code               2017488
_cod_database_fobs_code          2017488