Crystal structure of 4-chloro-2-nitrobenzoic acid with 4-hydroxyquinoline: a disordered structure over two states of 4-chloro-2-nitrobenzoic acid‒quinolin-4(1<i>H</i>)-one (1/1) and 4-hydroxyquinolinium 4-chloro-2-nitrobenzoate
Gotoh, Kazuma; Ishida, Hiroyuki; Acta Crystallographica Section E 75 (2019) 1853–1856; doi:10.1107/S205698901901497X

data_2243186
_publ_section_title
;
 Crystal structure of 4-chloro-2-nitrobenzoic acid with
 4-hydroxyquinoline: a disordered structure over two states of
 4-chloro-2-nitrobenzoic acid--quinolin-4(1<i>H</i>)-one (1/1) and
 4-hydroxyquinolinium 4-chloro-2-nitrobenzoate
;
_journal_coeditor_code           LH5935
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              1853
_journal_page_last               1856
_journal_paper_doi               10.1107/S205698901901497X
_journal_volume                  75
_journal_year                    2019
_chemical_formula_moiety         'C7 H3.5 Cl N O4, C9 H7.5 N O'
_chemical_formula_sum            'C16 H11 Cl N2 O5'
_chemical_formula_weight         346.73
_chemical_name_systematic
'4-Chloro-2-nitrobenzoic acid--quinolin-4(1<i>H</i>)-one (1/1)--4-hydroxyquinolinium 4-chloro-2-nitrobenzoate'
_space_group_crystal_system      orthorhombic
_space_group_IT_number           60
_space_group_name_Hall           '-P 2n 2ab'
_space_group_name_H-M_alt        'P b c n'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.0000
_cell_angle_beta                 90.0000
_cell_angle_gamma                90.0000
_cell_formula_units_Z            8
_cell_length_a                   12.6336(8)
_cell_length_b                   7.0701(3)
_cell_length_c                   33.5956(15)
_cell_measurement_reflns_used    23445
_cell_measurement_temperature    190.0(10)
_cell_measurement_theta_max      30.19
_cell_measurement_theta_min      3.03
_cell_volume                     3000.8(3)
_computing_cell_refinement
;
<i>PROCESS-AUTO</i> (Rigaku, 2006)
;
_computing_data_collection
;
<i>PROCESS-AUTO</i> (Rigaku, 2006)
;
_computing_data_reduction
;
<i>PROCESS-AUTO</i> (Rigaku, 2006)
;
_computing_molecular_graphics
;
<i>ORTEP-3 for Windows</i> and <i>WinGX</i> (Farrugia,  2012);
<i>Mercury</i> (Macrae <i>et al</i>., 2008)
;
_computing_publication_material
;
<i>CrystalStructure</i> (Rigaku, 2018) and <i>PLATON</i> (Spek,
2015)
;
_computing_structure_refinement
;
<i>SHELXL2018</i> (Sheldrick, 2015<i>b</i>)
;
_computing_structure_solution
;
<i>SHELXT2018</i> (Sheldrick, 2015<i>a</i>)
;
_diffrn_ambient_temperature      190(2)
_diffrn_detector_area_resol_mean 10.000
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPIDII'
_diffrn_measurement_method       \w
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0518
_diffrn_reflns_av_unetI/netI     0.0287
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       47
_diffrn_reflns_limit_l_min       -47
_diffrn_reflns_number            36709
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.033
_diffrn_reflns_theta_min         3.225
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.285
_exptl_absorpt_correction_T_max  0.975
_exptl_absorpt_correction_T_min  0.939
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
;
(<i>NUMABS</i>; Higashi, 1999)
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.535
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       platelet
_exptl_crystal_F_000             1424.00
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.280
_exptl_crystal_size_min          0.090
_refine_diff_density_max         0.391
_refine_diff_density_min         -0.417
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.130
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         4380
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.130
_refine_ls_R_factor_all          0.0631
_refine_ls_R_factor_gt           0.0456
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0641P)^2^+0.6358P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1185
_refine_ls_wR_factor_ref         0.1362
_reflns_number_gt                3235
_reflns_number_total             4380
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            lh5935sup1.cif
_cod_data_source_block           I
_cod_database_code               2243186
_shelx_hkl_checksum              1100
_shelx_res_checksum              84867
_cod_database_fobs_code 2243186