Two- and three-dimensional hydrogen-bonded structures in the 1:1 proton-transfer compounds of 4,5-dichlorophthalic acid with the isomeric monoaminobenzoic acids
Smith, Graham; Wermuth, Urs D.; White, Jonathan M.; Acta Crystallographica Section C 64 (2008) o532–o536; doi:10.1107/S0108270108027054

data_2016775
_publ_section_title
;
 Two- and three-dimensional hydrogen-bonded structures in the 1:1
 proton-transfer compounds of 4,5-dichlorophthalic acid with the
 isomeric monoaminobenzoic acids
;
_journal_coeditor_code           SF3087
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o532
_journal_page_last               o536
_journal_paper_doi               10.1107/S0108270108027054
_journal_volume                  64
_journal_year                    2008
_chemical_formula_iupac          'C7 H8 N O2 + , C8 H3 Cl2 O4 -'
_chemical_formula_moiety         'C7 H8 N O2 + , C8 H3 Cl2 O4 -'
_chemical_formula_sum            'C15 H11 Cl2 N O6'
_chemical_formula_weight         372.15
_chemical_melting_point_gt       573
_chemical_name_common
'3-carboxyanilinium hydrogen 4,5-dichlorophthalate'
_chemical_name_systematic
;
3-carboxyanilinium 2-carboxy-4,5-dichlorobenzoate
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/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                 96.0120(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   12.9028(7)
_cell_length_b                   7.4091(4)
_cell_length_c                   32.2323(17)
_cell_measurement_reflns_used    8197
_cell_measurement_temperature    130(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      2.61
_cell_volume                     3064.4(3)
_computing_cell_refinement       'SMART (Bruker, 2000)'
_computing_data_collection       'SMART (Bruker, 2000)'
_computing_data_reduction        'SAINT (Bruker, 1999)'
_computing_molecular_graphics    'PLATON (Spek, 2003)'
_computing_publication_material  'PLATON (Spek, 2003)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      130(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0219
_diffrn_reflns_av_sigmaI/netI    0.0273
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       41
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_number            17962
_diffrn_reflns_theta_full        27.5
_diffrn_reflns_theta_max         27.5
_diffrn_reflns_theta_min         1.27
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    0.457
_exptl_absorpt_correction_T_max  0.85
_exptl_absorpt_correction_T_min  0.74
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            'pale brown'
_exptl_crystal_density_diffrn    1.613
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1520
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.35
_refine_diff_density_max         0.446
_refine_diff_density_min         -0.412
_refine_ls_extinction_coef       0.00057(17)
_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   1.058
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     474
_refine_ls_number_reflns         6995
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0463
_refine_ls_R_factor_gt           0.0399
_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^)+(0.0567P)^2^+1.2365P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1005
_refine_ls_wR_factor_ref         0.1044
_reflns_number_gt                6125
_reflns_number_total             6995
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            sf3087.cif
_cod_data_source_block           II
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2016775
_cod_database_fobs_code          2016775