Zero-, one- and two-dimensional hydrogen-bonded structures in the 1:1 proton-transfer compounds of 4,5-dichlorophthalic acid with the monocyclic heteroaromatic Lewis bases 2-aminopyrimidine, nicotinamide and isonicotinamide
Smith, Graham; Wermuth, Urs D.; White, Jonathan M.; Acta Crystallographica Section C 65 (2009) o103–o107; doi:10.1107/S0108270109004405

data_2017007
_publ_section_title
;
 Zero-, one- and two-dimensional hydrogen-bonded structures in the 1:1
 proton-transfer compounds of 4,5-dichlorophthalic acid with the
 monocyclic heteroaromatic Lewis bases 2-aminopyrimidine, nicotinamide
 and isonicotinamide
;
_journal_coeditor_code           GD3270
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o103
_journal_page_last               o107
_journal_paper_doi               10.1107/S0108270109004405
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C6 H7 N2 O +, C8 H3 Cl2 O4 -, C9 H6 Cl2 O4'
_chemical_formula_moiety         'C6 H7 N2 O +, C8 H3 Cl2 O4 -, C9 H6 Cl2 O4'
_chemical_formula_sum            'C23 H16 Cl4 N2 O9'
_chemical_formula_weight         606.18
_chemical_melting_point_gt       433
_chemical_melting_point_lt       434
_chemical_name_common
;
isonicotinamidinium hydrogen 4,5-dichlorophthalate
methyl 4,5-dichlorophthalic acid adduct
;
_chemical_name_systematic
;
4-(aminocarbonyl)pyridinium 2-carboxy-4,5-dichlorobenzoate--
methyl 2-carboxy-4,5-dichlorobenzoate (1/1)
;
_space_group_IT_number           9
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C -2yc'
_symmetry_space_group_name_H-M   'C 1 c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                90
_cell_angle_beta                 122.509(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.9645(4)
_cell_length_b                   26.1393(6)
_cell_length_c                   9.3213(3)
_cell_measurement_reflns_used    2767
_cell_measurement_temperature    130(2)
_cell_measurement_theta_max      72.46
_cell_measurement_theta_min      3.38
_cell_volume                     2458.39(15)
_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)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      130(2)
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.957
_diffrn_measurement_device_type
'Oxford Diffraction Gemini-S Ultra CCD-detector diffractometer'
_diffrn_measurement_method       ' \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Cu) X-ray source'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0450
_diffrn_reflns_av_sigmaI/netI    0.0496
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            6097
_diffrn_reflns_reduction_process
;
?
;
_diffrn_reflns_theta_full        67.68
_diffrn_reflns_theta_max         72.89
_diffrn_reflns_theta_min         3.38
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    4.901
_exptl_absorpt_correction_T_max  0.710
_exptl_absorpt_correction_T_min  0.454
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.638
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1232
_exptl_crystal_size_max          0.560
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.070
_refine_diff_density_max         0.323
_refine_diff_density_min         -0.429
_refine_ls_abs_structure_details 'Flack (1983); 576 Friedel pairs'
_refine_ls_abs_structure_Flack   0.03(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.966
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     363
_refine_ls_number_reflns         3034
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.965
_refine_ls_R_factor_all          0.0525
_refine_ls_R_factor_gt           0.0464
_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^)+(0.0961P)^2^] WHERE P=(FO^2^+2FC^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1230
_refine_ls_wR_factor_ref         0.1280
_reflns_number_gt                2530
_reflns_number_total             3034
_reflns_threshold_expression     'I>2\s(I) '
_cod_data_source_file            gd3270.cif
_cod_data_source_block           III
_cod_original_sg_symbol_H-M      'C c'
_cod_database_code               2017007