Hydrogen-bonded structures of the isomeric compounds of quinoline with 2-chloro-5-nitrobenzoic acid, 3-chloro-2-nitrobenzoic acid, 4-chloro-2-nitrobenzoic acid and 5-chloro-2-nitrobenzoic acid
Gotoh, Kazuma; Ishida, Hiroyuki; Acta Crystallographica Section C 65 (2009) o534–o538; doi:10.1107/S0108270109037688

data_2017343
_publ_section_title
;
 Hydrogen-bonded structures of the isomeric compounds of quinoline with
 2-chloro-5-nitrobenzoic acid, 3-chloro-2-nitrobenzoic acid,
 4-chloro-2-nitrobenzoic acid and 5-chloro-2-nitrobenzoic acid
;
_journal_coeditor_code           GD3308
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o534
_journal_page_last               o538
_journal_paper_doi               10.1107/S0108270109037688
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C7 H4 Cl N O4, C9 H7 N'
_chemical_formula_moiety         'C7 H4 Cl N O4, C9 H7 N'
_chemical_formula_sum            'C16 H11 Cl N2 O4'
_chemical_formula_weight         330.73
_chemical_name_systematic
;
2-chloro-5-nitrobenzoic acid--quinoline (1/1)
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                75.861(4)
_cell_angle_beta                 89.207(3)
_cell_angle_gamma                79.842(4)
_cell_formula_units_Z            2
_cell_length_a                   6.9254(10)
_cell_length_b                   7.4746(11)
_cell_length_c                   14.310(2)
_cell_measurement_reflns_used    13073
_cell_measurement_temperature    185.0(10)
_cell_measurement_theta_max      30.1
_cell_measurement_theta_min      3.3
_cell_volume                     706.72(18)
_computing_cell_refinement       'PROCESS-AUTO (Rigaku/MSC, 2004)'
_computing_data_collection       'PROCESS-AUTO (Rigaku/MSC, 2004)'
_computing_data_reduction        'CrystalStructure (Rigaku/MSC, 2004)'
_computing_molecular_graphics
'ORTEP-3 (Farrugia, 1997) and WinGX (Farrugia, 1999)'
_computing_publication_material
'CrystalStructure (Rigaku/MSC, 2004) and  PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      185.0(10)
_diffrn_detector_area_resol_mean 10.00
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Rigaku RAXIS-RAPIDII'
_diffrn_measurement_method       \w
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0193
_diffrn_reflns_av_sigmaI/netI    0.0141
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            14562
_diffrn_reflns_theta_full        29.99
_diffrn_reflns_theta_max         29.99
_diffrn_reflns_theta_min         3.29
_exptl_absorpt_coefficient_mu    0.293
_exptl_absorpt_correction_T_max  0.943
_exptl_absorpt_correction_T_min  0.932
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
;
(<i>ABSCOR</i>; Higashi, 1995)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.554
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             340.00
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.438
_refine_diff_density_min         -0.245
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     212
_refine_ls_number_reflns         4109
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0365
_refine_ls_R_factor_gt           0.0325
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0549P)^2^+0.1631P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0925
_refine_ls_wR_factor_ref         0.0957
_reflns_number_gt                3703
_reflns_number_total             4109
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            gd3308.cif
_cod_data_source_block           I
_cod_original_cell_volume        706.71(17)
_cod_database_code               2017343
_cod_database_fobs_code          2017343