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_2016774
_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 - , 2H2 O'
_chemical_formula_moiety         'C7 H8 N O2 + , C8 H3 Cl2 O4 - , 2H2 O'
_chemical_formula_sum            'C15 H15 Cl2 N O8'
_chemical_formula_weight         408.18
_chemical_melting_point_gt       437
_chemical_melting_point_lt       438
_chemical_name_common
'2-carboxyanilinium hydrogen 4,5-dichlorophthalate dihydrate'
_chemical_name_systematic
;
2-carboxyanilinium 2-carboxy-4,5-dichlorobenzoate dihydrate
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           'SHELXL97 (Sheldrick, 1997)'
_cell_angle_alpha                86.525(6)
_cell_angle_beta                 87.481(6)
_cell_angle_gamma                86.190(6)
_cell_formula_units_Z            2
_cell_length_a                   6.7684(5)
_cell_length_b                   6.9561(4)
_cell_length_c                   18.0001(14)
_cell_measurement_reflns_used    3819
_cell_measurement_temperature    180(2)
_cell_measurement_theta_max      72.085
_cell_measurement_theta_min      4.9260
_cell_volume                     843.37(10)
_computing_cell_refinement       'CrysAlis RED (Oxford Diffraction, 2007)'
_computing_data_collection       'CrysAlis CCD (Oxford Diffraction, 2007)'
_computing_data_reduction        'CrysAlis RED (Oxford Diffraction, 2007)'
_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      180(2)
_diffrn_detector_area_resol_mean 16.0711
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.956
_diffrn_measurement_device_type
'Oxford Diffraction Gemini S Ultra CCD area-detector'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Cu) X-ray Source'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.0393
_diffrn_reflns_av_sigmaI/netI    0.0353
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            7458
_diffrn_reflns_theta_full        70.0
_diffrn_reflns_theta_max         72.0
_diffrn_reflns_theta_min         4.93
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    3.899
_exptl_absorpt_correction_T_max  0.580
_exptl_absorpt_correction_T_min  0.260
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.607
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             420
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.425
_refine_diff_density_min         -0.481
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.093
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     271
_refine_ls_number_reflns         3190
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.093
_refine_ls_R_factor_all          0.0541
_refine_ls_R_factor_gt           0.0499
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[\s^2^(Fo^2^)+(0.1194P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1526
_refine_ls_wR_factor_ref         0.1568
_reflns_number_gt                2691
_reflns_number_total             3190
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            sf3087.cif
_cod_data_source_block           I
_cod_database_code               2016774
_cod_database_fobs_code          2016774