Crystal structure and Hirshfeld surface analysis of <i>N</i>-(2-chlorophenylcarbamothioyl)-4-fluorobenzamide and <i>N</i>-(4-bromophenylcarbamothioyl)-4-fluorobenzamide
Akhter, Sidra; Choudhary, Muhammad Iqbal; Siddiqui, Hina; Yousuf, Sammer; Acta Crystallographica Section E 75 (2019) 1026–1029; doi:10.1107/S2056989019008569

data_2242984
_publ_section_title
;
 Crystal structure and Hirshfeld surface analysis of
 <i>N</i>-(2-chlorophenylcarbamothioyl)-4-fluorobenzamide and
 <i>N</i>-(4-bromophenylcarbamothioyl)-4-fluorobenzamide
;
_journal_coeditor_code           HB7804
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              1026
_journal_page_last               1029
_journal_paper_doi               10.1107/S2056989019008569
_journal_volume                  75
_journal_year                    2019
_chemical_formula_iupac          'C14 H10 Cl F N2 O S'
_chemical_formula_moiety         'C14 H10 Cl F N2 O S'
_chemical_formula_sum            'C14 H10 Cl F N2 O S'
_chemical_formula_weight         308.75
_chemical_name_systematic
;
<i>N</i>-(2-Chlorophenylcarbamothioyl)-4-fluorobenzamide
;
_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'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_method           SHELXL-2016/6
_cell_angle_alpha                90
_cell_angle_beta                 90.5510(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.0785(2)
_cell_length_b                   12.4230(3)
_cell_length_c                   13.0772(3)
_cell_measurement_reflns_used    9977
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      68.27
_cell_measurement_theta_min      4.91
_cell_volume                     1312.36(5)
_computing_cell_refinement
;
SAINT (Bruker, 2000)
;
_computing_data_collection
;
APEX2 (Bruker, 2000)
;
_computing_data_reduction
;
SAINT (Bruker, 2000)
;
_computing_molecular_graphics
;
SHELXTL (Sheldrick, 2008)
;
_computing_publication_material
;
SHELXTL (Sheldrick, 2008)
;
_computing_structure_refinement
;
SHELXL2016 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT2014 (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       \w
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0231
_diffrn_reflns_av_unetI/netI     0.0135
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            18686
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.267
_diffrn_reflns_theta_min         4.910
_exptl_absorpt_coefficient_mu    4.152
_exptl_absorpt_correction_T_max  0.8950
_exptl_absorpt_correction_T_min  0.6820
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2000)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.563
_exptl_crystal_description       Prism
_exptl_crystal_F_000             632
_exptl_crystal_size_max          0.110
_exptl_crystal_size_mid          0.070
_exptl_crystal_size_min          0.030
_refine_diff_density_max         0.220
_refine_diff_density_min         -0.245
_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     189
_refine_ls_number_reflns         2362
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0265
_refine_ls_R_factor_gt           0.0254
_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^)+(0.0347P)^2^+0.7594P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0681
_refine_ls_wR_factor_ref         0.0689
_reflns_number_gt                2269
_reflns_number_total             2362
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            hb7804sup1.cif
_cod_data_source_block           1
_cod_database_code               2242984
_cod_database_fobs_code          2242984
_shelx_estimated_absorpt_t_min   0.658
_shelx_estimated_absorpt_t_max   0.886
_shelx_hkl_checksum              96884
_shelx_res_checksum              40680