Crystal structures of the two isomeric hydrogen-bonded cocrystals 2-chloro-4-nitrobenzoic acid–5-nitroquinoline (1/1) and 5-chloro-2-nitrobenzoic acid–5-nitroquinoline (1/1)
Gotoh, Kazuma; Ishida, Hiroyuki; Acta Crystallographica Section E 75 (2019) 1694–1699; doi:10.1107/S2056989019013896

data_2243148
_publ_section_title
;
 Crystal structures of the two isomeric hydrogen-bonded cocrystals
 2-chloro-4-nitrobenzoic acid--5-nitroquinoline (1/1) and
 5-chloro-2-nitrobenzoic acid--5-nitroquinoline (1/1)
;
_journal_coeditor_code           LH5931
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              1694
_journal_page_last               1699
_journal_paper_doi               10.1107/S2056989019013896
_journal_volume                  75
_journal_year                    2019
_chemical_formula_iupac          'C7 H4 Cl N O4, C9 H6 N2 O2'
_chemical_formula_moiety         'C7 H4 Cl N O4, C9 H6 N2 O2'
_chemical_formula_sum            'C16 H10 Cl N3 O6'
_chemical_formula_weight         375.72
_chemical_name_systematic
;
5-Chloro-2-nitrobenzoic acid--5-nitroquinoline (1/1)
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                79.170(3)
_cell_angle_beta                 78.968(2)
_cell_angle_gamma                70.394(3)
_cell_formula_units_Z            2
_cell_length_a                   7.6682(6)
_cell_length_b                   8.6515(8)
_cell_length_c                   12.8609(10)
_cell_measurement_reflns_used    7062
_cell_measurement_temperature    190.0(10)
_cell_measurement_theta_max      30.05
_cell_measurement_theta_min      3.08
_cell_volume                     781.80(11)
_computing_cell_refinement
;
PROCESS-AUTO (Rigaku, 2006)
;
_computing_data_collection
;
PROCESS-AUTO (Rigaku, 2006)
;
_computing_data_reduction
;
PROCESS-AUTO (Rigaku, 2006)
;
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 2012) and Mercury (Macrae <i>et al.</i>,
2008)
;
_computing_publication_material
;
CrystalStructure (Rigaku, 2018) and PLATON (Spek, 2015)
;
_computing_structure_refinement
;
SHELXL2018 (Sheldrick, 2015<i>b</i>)
;
_computing_structure_solution
;
SHELXT2018 (Sheldrick, 2015<i>a</i>)
;
_diffrn_ambient_temperature      190.0(10)
_diffrn_detector_area_resol_mean 10.000
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       \w
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0549
_diffrn_reflns_av_unetI/netI     0.0622
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            9772
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.986
_diffrn_reflns_theta_min         3.078
_exptl_absorpt_coefficient_mu    0.287
_exptl_absorpt_correction_T_max  0.950
_exptl_absorpt_correction_T_min  0.933
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
;
(NUMABS; Higashi, 1999)
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.596
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             384.00
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.180
_refine_diff_density_max         0.417
_refine_diff_density_min         -0.386
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     239
_refine_ls_number_reflns         4502
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.086
_refine_ls_R_factor_all          0.0758
_refine_ls_R_factor_gt           0.0517
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0770P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1320
_refine_ls_wR_factor_ref         0.1479
_reflns_number_gt                3075
_reflns_number_total             4502
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            lh5931sup1.cif
_cod_data_source_block           II
_cod_database_code               2243148
_cod_database_fobs_code          2243148
_shelx_hkl_checksum              68932
_shelx_res_checksum              33951