Crystal structure, Hirshfeld surface analysis and DFT study of (2<i>Z</i>)-2-(4-fluorobenzylidene)-4-(prop-2-yn-1-yl)-3,4-dihydro-2<i>H</i>-1,4-benzothiazin-3-one
Hni, Brahim; Sebbar, Nada Kheira; Hökelek, Tuncer; Ouzidan, Younes; Moussaif, Ahmed; Mague, Joel T.; Essassi, El Mokhtar; Acta Crystallographica Section E 75 (2019) 372–377; doi:10.1107/S2056989019002354

data_2242856
_publ_section_title
;
 Crystal structure, Hirshfeld surface analysis and DFT study of
 (2<i>Z</i>)-2-(4-fluorobenzylidene)-4-(prop-2-yn-1-yl)-3,4-dihydro-2<i>H</i>-1,4-benzothiazin-3-one
;
_journal_coeditor_code           LH5893
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              372
_journal_page_last               377
_journal_paper_doi               10.1107/S2056989019002354
_journal_volume                  75
_journal_year                    2019
_chemical_formula_iupac          'C18 H12 F N O S'
_chemical_formula_moiety         'C18 H12 F N O S'
_chemical_formula_sum            'C18 H12 F N O S'
_chemical_formula_weight         309.35
_chemical_name_systematic
(2<i>Z</i>)-2-(4-Fluorobenzylidene)-4-(prop-2-yn-1-yl)-3,4-dihydro-2<i>H</i>-1,4-benzothiazin-3-one
_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   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/1
_cell_angle_alpha                117.809(2)
_cell_angle_beta                 93.155(2)
_cell_angle_gamma                94.416(2)
_cell_formula_units_Z            2
_cell_length_a                   4.0602(2)
_cell_length_b                   13.8983(5)
_cell_length_c                   14.2620(5)
_cell_measurement_reflns_used    4191
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      72.249
_cell_measurement_theta_min      3.620
_cell_volume                     705.96(5)
_computing_cell_refinement
;
<i>SAINT</i> (Bruker, 2016)
;
_computing_data_collection
;
<i>APEX3</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 0.953
_diffrn_measured_fraction_theta_max 0.939
_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  0.0264
_diffrn_reflns_av_unetI/netI     0.0359
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            5323
_diffrn_reflns_theta_full        69.000
_diffrn_reflns_theta_max         72.242
_diffrn_reflns_theta_min         3.620
_diffrn_source                   'INCOATEC I\mS micro-focus source'
_exptl_absorpt_coefficient_mu    2.145
_exptl_absorpt_correction_T_max  0.97
_exptl_absorpt_correction_T_min  0.69
_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    1.455
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             320
_exptl_crystal_size_max          0.454
_exptl_crystal_size_mid          0.214
_exptl_crystal_size_min          0.014
_refine_diff_density_max         0.229
_refine_diff_density_min         -0.310
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     247
_refine_ls_number_reflns         2595
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0426
_refine_ls_R_factor_gt           0.0360
_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^+0.2564P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0876
_refine_ls_wR_factor_ref         0.0922
_reflns_number_gt                2256
_reflns_number_total             2595
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            lh5893sup1.cif
_cod_data_source_block           I
_cod_database_code               2242856
_cod_database_fobs_code          2242856
_shelx_estimated_absorpt_t_min   0.443
_shelx_estimated_absorpt_t_max   0.971
_shelx_hkl_checksum              17971
_shelx_res_checksum              24402