2-Chloro-3-nitro-5-(trifluoromethyl)benzoic acid and -benzamide: structural characterization of two precursors for antitubercular benzothiazinones
Richter, Adrian; Goddard, Richard; Schlegel, Tom; Imming, Peter; Seidel, Rüdiger W.; Acta Crystallographica Section E 77 (2021) 142–147; doi:10.1107/S2056989021000517

data_2243728
_publ_section_title
;
 2-Chloro-3-nitro-5-(trifluoromethyl)benzoic acid and -benzamide:
 structural characterization of two precursors for antitubercular
 benzothiazinones
;
_journal_coeditor_code           TX2035
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              142
_journal_page_last               147
_journal_paper_doi               10.1107/S2056989021000517
_journal_volume                  77
_journal_year                    2021
_chemical_formula_iupac          'C8 H4 Cl F3 N2 O3'
_chemical_formula_moiety         'C8 H4 Cl F3 N2 O3'
_chemical_formula_sum            'C8 H4 Cl F3 N2 O3'
_chemical_formula_weight         268.58
_chemical_name_systematic
;
2-Chloro-3-nitro-5-(trifluoromethyl)benzamide
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 110.424(3)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   8.3012(12)
_cell_length_b                   28.230(4)
_cell_length_c                   9.1522(14)
_cell_measurement_reflns_used    8332
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      31.9594
_cell_measurement_theta_min      2.7159
_cell_volume                     2009.9(5)
_computing_cell_refinement
;
SAINT (Bruker, 2004)
;
_computing_data_collection
;
APEX3 (Bruker, 2017)
;
_computing_data_reduction
;
SAINT (Bruker, 2004)
;
_computing_molecular_graphics
;
DIAMOND (Brandenburg, 2018)
;
_computing_publication_material
;
enCIFer (Allen <i>et al.</i>,  2004) and publCIF (Westrip, 2010)
;
_computing_structure_refinement
;
SHELXL (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 66.67
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Bruker Kappa Mach3 APEXII'
_diffrn_measurement_method       '\f- and \w-scans'
_diffrn_radiation_monochromator  'Incoatec Helios mirrors'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0795
_diffrn_reflns_av_unetI/netI     0.0538
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       43
_diffrn_reflns_limit_k_min       -44
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            64252
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         34.311
_diffrn_reflns_theta_min         1.443
_diffrn_source                   'microfocus X-ray tube'
_exptl_absorpt_coefficient_mu    0.423
_exptl_absorpt_correction_T_max  0.99614
_exptl_absorpt_correction_T_min  0.98906
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2012)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.775
_exptl_crystal_description       prism
_exptl_crystal_F_000             1072
_exptl_crystal_size_max          0.046
_exptl_crystal_size_mid          0.016
_exptl_crystal_size_min          0.011
_refine_diff_density_max         0.791
_refine_diff_density_min         -0.592
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     329
_refine_ls_number_reflns         8316
_refine_ls_number_restraints     121
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0971
_refine_ls_R_factor_gt           0.0559
_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^)+(0.0470P)^2^+2.2564P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1188
_refine_ls_wR_factor_ref         0.1357
_reflns_number_gt                5593
_reflns_number_total             8316
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            tx2035sup1.cif
_cod_data_source_block           2
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2243728
_cod_database_fobs_code          2243728
_shelx_estimated_absorpt_t_min   0.981
_shelx_estimated_absorpt_t_max   0.995
_shelx_hkl_checksum              2742
_shelx_res_checksum              99484