Hydrogen bonding and π–π interactions in 1-benzofuran-2,3-dicarboxylic acid and its 1:1 cocrystals with pyridine, phenazine and 1,4-phenylenediamine
Titi, Hatem M.; Goldberg, Israel; Acta Crystallographica Section C 65 (2009) o639–o644; doi:10.1107/S0108270109047519

data_2017437
_publ_section_title
;
 Hydrogen bonding and \p--\p interactions in
 1-benzofuran-2,3-dicarboxylic acid and its 1:1 cocrystals with
 pyridine, phenazine and 1,4-phenylenediamine
;
_journal_coeditor_code           GD3317
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o639
_journal_page_last               o644
_journal_paper_doi               10.1107/S0108270109047519
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C12 H9 N2 + , C10 H5 O5 -'
_chemical_formula_moiety         'C12 H9 N2 + , C10 H5 O5 -'
_chemical_formula_sum            'C22 H14 N2 O5'
_chemical_formula_weight         386.35
_chemical_name_systematic
;
Phenazinium 3-carboxylato-1-benzofuran-2-carboxylic acid
;
_space_group_IT_number           7
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P -2yac'
_symmetry_space_group_name_H-M   'P 1 n 1'
_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                 90.3794(18)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   5.3881(2)
_cell_length_b                   8.3227(4)
_cell_length_c                   18.6514(11)
_cell_measurement_reflns_used    2631
_cell_measurement_temperature    110(2)
_cell_measurement_theta_max      27.83
_cell_measurement_theta_min      2.32
_cell_volume                     836.38(7)
_computing_cell_refinement       'DENZO (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius, 1999)'
_computing_data_reduction        'DENZO (Otwinowski & Minor, 1997)'
_computing_molecular_graphics
;
ORTEPIII (Burnett & Johnson, 1996) and Mercury (Macrae <i>et al.</i>,
2006)
;
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR97 (Altomare <i>et al.</i>,  1994)'
_diffrn_ambient_temperature      110(2)
_diffrn_detector_area_resol_mean 12.8
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Nonius KappaCCD area-detector'
_diffrn_measurement_method       '1 deg. \f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0443
_diffrn_reflns_av_sigmaI/netI    0.0758
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            7323
_diffrn_reflns_theta_full        27.83
_diffrn_reflns_theta_max         27.83
_diffrn_reflns_theta_min         3.28
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.111
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.534
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             400
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.284
_refine_diff_density_min         -0.214
_refine_ls_extinction_coef       0.014(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     269
_refine_ls_number_reflns         1970
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.023
_refine_ls_R_factor_all          0.0810
_refine_ls_R_factor_gt           0.0448
_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/[\s^2^(Fo^2^)+(0.0543P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0918
_refine_ls_wR_factor_ref         0.1051
_reflns_number_gt                1352
_reflns_number_total             1970
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            gd3317.cif
_cod_data_source_block           III
_cod_original_sg_symbol_H-M      'P n'
_cod_database_code               2017437
_cod_database_fobs_code          2017437