Crystal structures of 3-chloro-2-nitrobenzoic acid with quinoline derivatives: 3-chloro-2-nitrobenzoic acid–5-nitroquinoline (1/1), 3-chloro-2-nitrobenzoic acid–6-nitroquinoline (1/1) and 8-hydroxyquinolinium 3-chloro-2-nitrobenzoate
Gotoh, Kazuma; Ishida, Hiroyuki; Acta Crystallographica Section E 75 (2019) 1552–1557; doi:10.1107/S2056989019012799

data_2243114
_publ_section_title
;
 Crystal structures of 3-chloro-2-nitrobenzoic acid with quinoline
 derivatives: 3-chloro-2-nitrobenzoic acid--5-nitroquinoline (1/1),
 3-chloro-2-nitrobenzoic acid--6-nitroquinoline (1/1) and
 8-hydroxyquinolinium 3-chloro-2-nitrobenzoate
;
_journal_coeditor_code           LH5922
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              1552
_journal_page_last               1557
_journal_paper_doi               10.1107/S2056989019012799
_journal_volume                  75
_journal_year                    2019
_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
;
3-Chloro-2-nitrobenzoic acid--5-nitroquinoline (1/1)
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.0000
_cell_angle_beta                 104.5338(7)
_cell_angle_gamma                90.0000
_cell_formula_units_Z            8
_cell_length_a                   20.5876(4)
_cell_length_b                   7.6889(3)
_cell_length_c                   20.4312(4)
_cell_measurement_reflns_used    25710
_cell_measurement_temperature    190.0(10)
_cell_measurement_theta_max      30.10
_cell_measurement_theta_min      3.09
_cell_volume                     3130.68(15)
_computing_cell_refinement
;
RAPID-AUTO (Rigaku, 2006)
;
_computing_data_collection
;
RAPID-AUTO (Rigaku, 2006)
;
_computing_data_reduction
;
RAPID-AUTO (Rigaku, 2006)
;
_computing_molecular_graphics
;
<i>ORTEP-3 for Windows</i> (Farrugia, 2012) and
Mercury (Macrae <i>et al</i>., 2006)
;
_computing_publication_material
;
CrystalStructure (Rigaku, 2018) and PLATON (Spek, 2015)
;
_computing_structure_refinement
;
<i>SHELXL2018/3</i> (Sheldrick, 2015<i>b</i>)
;
_computing_structure_solution
;
<i>SHELXT2018/2</i> (Sheldrick, 2015<i>a</i>)
;
_diffrn_ambient_temperature      190(2)
_diffrn_detector_area_resol_mean 10.000
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  0.0219
_diffrn_reflns_av_unetI/netI     0.0119
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            30107
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.982
_diffrn_reflns_theta_min         3.107
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.286
_exptl_absorpt_correction_T_max  0.918
_exptl_absorpt_correction_T_min  0.837
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
;
(<i>NUMABS</i>; Higashi, 1999)
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.594
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1536.00
_exptl_crystal_size_max          0.450
_exptl_crystal_size_mid          0.400
_exptl_crystal_size_min          0.300
_refine_diff_density_max         0.297
_refine_diff_density_min         -0.347
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     239
_refine_ls_number_reflns         4549
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0407
_refine_ls_R_factor_gt           0.0368
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[\s^2^(Fo^2^)+(0.0636P)^2^+1.2587P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0994
_refine_ls_wR_factor_ref         0.1036
_reflns_number_gt                4077
_reflns_number_total             4549
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            lh5922sup1.cif
_cod_data_source_block           I
_cod_original_cell_volume        3130.70(16)
_cod_database_code               2243114
_cod_database_fobs_code          2243114
_shelx_hkl_checksum              55853
_shelx_res_checksum              38103