One-dimensional hydrogen-bonded structures in the 1:1 proton-transfer compounds of 4,5-dichlorophthalic acid with 8-hydroxyquinoline, 8-aminoquinoline and quinoline-2-carboxylic acid (quinaldic acid)
Smith, Graham; Wermuth, Urs D.; White, Jonathan M.; Acta Crystallographica Section C 64 (2008) o180–o183; doi:10.1107/S0108270108004034

data_2016486
_publ_section_title
;
 One-dimensional hydrogen-bonded structures in the 1:1 proton-transfer
 compounds of 4,5-dichlorophthalic acid with 8-hydroxyquinoline,
 8-aminoquinoline and quinoline-2-carboxylic acid (quinaldic acid)
;
_journal_coeditor_code           GD3186
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o180
_journal_page_last               o183
_journal_paper_doi               10.1107/S0108270108004034
_journal_volume                  64
_journal_year                    2008
_chemical_formula_iupac
'C10 H8 N O2 + , C8 H3 Cl2 O4 - , C10 H7 N O2 , H2 O'
_chemical_formula_moiety
'C10 H8 N O2 + , C8 H3 Cl2 O4 - , C10 H7 N O2 , H2 O'
_chemical_formula_sum            'C28 H20 Cl2 N2 O9'
_chemical_formula_weight         599.36
_chemical_melting_point          455
_chemical_name_common
;
2-carboxyquinolinium hydrogen 4,5-dichlorophthalate quinaldic
acid monohydrate
;
_chemical_name_systematic
;
2-carboxyquinolinium 2-carboxy-4,5-dichlorobenzoate quinolinium
2-carboxylate monohydrate
;
_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, 2008)'
_cell_angle_alpha                87.558(2)
_cell_angle_beta                 88.577(2)
_cell_angle_gamma                83.996(2)
_cell_formula_units_Z            2
_cell_length_a                   7.1893(9)
_cell_length_b                   10.1172(13)
_cell_length_c                   19.520(3)
_cell_measurement_reflns_used    2565
_cell_measurement_temperature    130(2)
_cell_measurement_theta_max      25
_cell_measurement_theta_min      3
_cell_volume                     1410.4(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 0.981
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       '\f and \w'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0939
_diffrn_reflns_av_sigmaI/netI    0.0708
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            6939
_diffrn_reflns_theta_full        24.99
_diffrn_reflns_theta_max         24.99
_diffrn_reflns_theta_min         1.04
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    0.287
_exptl_absorpt_correction_T_max  0.931
_exptl_absorpt_correction_T_min  0.865
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.407
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             616
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.667
_refine_diff_density_min         -0.513
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     390
_refine_ls_number_reflns         4878
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.0668
_refine_ls_R_factor_gt           0.0587
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[\s^2^(Fo^2^)+(0.1022P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1538
_refine_ls_wR_factor_ref         0.1600
_reflns_number_gt                3980
_reflns_number_total             4878
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            gd3186.cif
_cod_data_source_block           III
_cod_database_code               2016486
_cod_database_fobs_code          2016486