Crystal structure, Hirshfeld surface analysis and interaction energy and DFT studies of 3-{(2<i>Z</i>)-2-[(2,4-dichlorophenyl)methylidene]-3-oxo-3,4-dihydro-2<i>H</i>-1,4-benzothiazin-4-yl}propanenitrile
Sebbar, Nada Kheira; Hni, Brahim; Hökelek, Tuncer; Jaouhar, Abdelhakim; Labd Taha, Mohamed; Mague, Joel T.; Essassi, El Mokhtar; Acta Crystallographica Section E 75 (2019) 721–727; doi:10.1107/S2056989019005966

data_2242928
_publ_section_title
;
 Crystal structure, Hirshfeld surface analysis and interaction energy and
 DFT studies of
 3-{(2<i>Z</i>)-2-[(2,4-dichlorophenyl)methylidene]-3-oxo-3,4-dihydro-2<i>H</i>-1,4-benzothiazin-4-yl}propanenitrile
;
_journal_coeditor_code           LH5901
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              721
_journal_page_last               727
_journal_paper_doi               10.1107/S2056989019005966
_journal_volume                  75
_journal_year                    2019
_chemical_formula_iupac          'C18 H12 Cl2 N2 O S'
_chemical_formula_moiety         'C18 H12 Cl2 N2 O S'
_chemical_formula_sum            'C18 H12 Cl2 N2 O S'
_chemical_formula_weight         375.26
_chemical_name_systematic
3-{(2<i>Z</i>)-2-[(2,4-Dichlorophenyl)methylidene]-3-oxo-3,4-dihydro-2<i>H</i>-1,4-benzothiazin-4-yl}propanenitrile
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_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
_audit_creation_method           SHELXL-2018/1
_cell_angle_alpha                98.105(4)
_cell_angle_beta                 94.316(4)
_cell_angle_gamma                95.002(4)
_cell_formula_units_Z            2
_cell_length_a                   6.5687(6)
_cell_length_b                   7.9971(7)
_cell_length_c                   15.4939(13)
_cell_measurement_reflns_used    5359
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      72.376
_cell_measurement_theta_min      5.616
_cell_volume                     799.54(12)
_computing_cell_refinement
;
<i>SAINT</i> (Bruker, 2016)
;
_computing_data_reduction
;
<i>SAINT</i> (Bruker, 2016)
;
_computing_molecular_graphics
;
<i>DIAMOND</i> (Brandenburg & Putz, 2012)
;
_computing_publication_material
;
<i>SHELXTL</i> (Sheldrick, 2008)
;
_computing_structure_refinement
;
<i>SHELXL2018</i> (Sheldrick, 2015<i>b</i>)
;
_computing_structure_solution
;
<i>SHELXT</i> (Sheldrick, 2015<i>a</i>)
;
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 10.4167
_diffrn_measured_fraction_theta_full 0.963
_diffrn_measured_fraction_theta_max 0.943
_diffrn_measurement_device_type  'Bruker D8 VENTURE PHOTON 100 CMOS'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0301
_diffrn_reflns_av_unetI/netI     0.0405
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            6131
_diffrn_reflns_theta_full        69.000
_diffrn_reflns_theta_max         72.404
_diffrn_reflns_theta_min         5.615
_diffrn_source                   'INCOATEC I\mS micro-focus source'
_exptl_absorpt_coefficient_mu    4.934
_exptl_absorpt_correction_T_max  0.65
_exptl_absorpt_correction_T_min  0.47
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
;
(<i>SADABS</i>; Krause <i>et al.</i>, 2015)
;
_exptl_crystal_colour            'light yellow'
_exptl_crystal_density_diffrn    1.559
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             384
_exptl_crystal_size_max          0.199
_exptl_crystal_size_mid          0.139
_exptl_crystal_size_min          0.097
_refine_diff_density_max         0.247
_refine_diff_density_min         -0.347
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         2978
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0385
_refine_ls_R_factor_gt           0.0353
_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^)+(0.0424P)^2^+0.4609P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0926
_refine_ls_wR_factor_ref         0.0952
_reflns_number_gt                2744
_reflns_number_total             2978
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            lh5901sup1.cif
_cod_data_source_block           I
_cod_database_code               2242928
_cod_database_fobs_code          2242928
_shelx_estimated_absorpt_t_min   0.440
_shelx_estimated_absorpt_t_max   0.646
_shelx_hkl_checksum              47609
_shelx_res_checksum              35767