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_2016484
_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          'C9 H8 N O + , C8 H3 Cl2 O4 -'
_chemical_formula_moiety         'C9 H8 N O + , C8 H3 Cl2 O4 -'
_chemical_formula_sum            'C17 H11 Cl2 N O5'
_chemical_formula_weight         380.17
_chemical_melting_point          499
_chemical_name_common
'8-hydroxyquinolinium hydrogen 4,5-dichlorophthalate'
_chemical_name_systematic
;
8-hydroxyquinolinium 2-carboxy-4,5-dichlorobenzoate
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           'SHELXL97 (Sheldrick, 2008)'
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.8915(3)
_cell_length_b                   7.2887(2)
_cell_length_c                   30.8009(8)
_cell_measurement_reflns_used    3863
_cell_measurement_temperature    130(2)
_cell_measurement_theta_max      73.3959
_cell_measurement_theta_min      4.3141
_cell_volume                     1547.13(9)
_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      130(2)
_diffrn_detector_area_resol_mean 16.0711
_diffrn_measured_fraction_theta_full 0.959
_diffrn_measured_fraction_theta_max 0.960
_diffrn_measurement_device_type
'Oxford Diffraction Xcalibur KM4 CCD area-detector'
_diffrn_measurement_method       '\f and \w'
_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  0.0354
_diffrn_reflns_av_sigmaI/netI    0.0215
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_number            4879
_diffrn_reflns_theta_full        73.44
_diffrn_reflns_theta_max         73.44
_diffrn_reflns_theta_min         5.75
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    4.061
_exptl_absorpt_correction_T_max  0.443
_exptl_absorpt_correction_T_min  0.112
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.632
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             776
_exptl_crystal_size_max          0.614
_exptl_crystal_size_mid          0.560
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.401
_refine_diff_density_min         -0.257
_refine_ls_abs_structure_details 'Flack (1983), with 662 Friedel pairs'
_refine_ls_abs_structure_Flack   0.035(15)
_refine_ls_extinction_coef       0.0072(7)
_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   1.062
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     239
_refine_ls_number_reflns         2506
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.062
_refine_ls_R_factor_all          0.0363
_refine_ls_R_factor_gt           0.0357
_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^)+(0.078P)^2^+0.296P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0981
_refine_ls_wR_factor_ref         0.0985
_reflns_number_gt                2437
_reflns_number_total             2506
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            gd3186.cif
_cod_data_source_block           I
_cod_database_code               2016484
_cod_database_fobs_code          2016484