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_2243147
_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_absolute_configuration ad
_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
;
2-Chloro-4-nitrobenzoic acid--5-nitroquinoline
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.0000
_cell_angle_beta                 109.713(3)
_cell_angle_gamma                90.0000
_cell_formula_units_Z            2
_cell_length_a                   12.8265(13)
_cell_length_b                   4.7699(5)
_cell_length_c                   13.5033(16)
_cell_measurement_reflns_used    11483
_cell_measurement_temperature    190.0(10)
_cell_measurement_theta_max      30.04
_cell_measurement_theta_min      3.08
_cell_volume                     777.73(15)
_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(2)
_diffrn_detector_area_resol_mean 10.000
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.998
_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  0.0578
_diffrn_reflns_av_unetI/netI     0.0535
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            14435
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.982
_diffrn_reflns_theta_min         3.077
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.288
_exptl_absorpt_correction_T_max  0.972
_exptl_absorpt_correction_T_min  0.913
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
;
(NUMABS; Higashi, 1999)
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.604
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             384.00
_exptl_crystal_size_max          0.370
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.339
_refine_diff_density_min         -0.645
_refine_ls_abs_structure_details
;
Flack <i>x</i> determined using 898 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons <i>et al.</i>, 2013)
;
_refine_ls_abs_structure_Flack   0.01(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     239
_refine_ls_number_reflns         4168
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0759
_refine_ls_R_factor_gt           0.0556
_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^)+(0.0939P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1487
_refine_ls_wR_factor_ref         0.1688
_reflns_number_gt                2859
_reflns_number_total             4168
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            lh5931sup1.cif
_cod_data_source_block           I
_cod_database_code               2243147
_cod_database_fobs_code          2243147
_shelx_estimated_absorpt_t_min   0.901
_shelx_estimated_absorpt_t_max   0.972
_shelx_hkl_checksum              81756
_shelx_res_checksum              8526