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_2017006
_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 -'
_chemical_formula_moiety         'C6 H7 N2 O +, C8 H3 Cl2 O4 -'
_chemical_formula_sum            'C14 H10 Cl2 N2 O5'
_chemical_formula_weight         357.14
_chemical_melting_point_gt       455
_chemical_melting_point_lt       457
_chemical_name_common            'nicotinamidium hydrogen 4,5-dichlorophthalate'
_chemical_name_systematic
;
3-(aminocarbonyl)pyridinium 2-carboxy-4,5-dichlorobenzoate
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 99.454(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.4303(3)
_cell_length_b                   13.7933(3)
_cell_length_c                   9.2082(2)
_cell_measurement_reflns_used    3546
_cell_measurement_temperature    130(2)
_cell_measurement_theta_max      72.8973
_cell_measurement_theta_min      3.1994
_cell_volume                     1432.06(6)
_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 0.999
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_device_type
'Oxford Diffraction Gemini-S 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     1.54184
_diffrn_reflns_av_R_equivalents  0.0260
_diffrn_reflns_av_sigmaI/netI    0.0300
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            6939
_diffrn_reflns_theta_full        67.68
_diffrn_reflns_theta_max         72.86
_diffrn_reflns_theta_min         3.92
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    4.360
_exptl_absorpt_correction_T_max  0.740
_exptl_absorpt_correction_T_min  0.340
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.656
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.340
_refine_diff_density_min         -0.220
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.956
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     224
_refine_ls_number_reflns         2798
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.956
_refine_ls_R_factor_all          0.0448
_refine_ls_R_factor_gt           0.0350
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0656P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0915
_refine_ls_wR_factor_ref         0.0950
_reflns_number_gt                2237
_reflns_number_total             2798
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            gd3270.cif
_cod_data_source_block           II
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2017006