#------------------------------------------------------------------------------
#$Date: 2020-05-23 08:14:40 +0300 (Sat, 23 May 2020) $
#$Revision: 252317 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/24/34/2243403.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2243403
loop_
_publ_author_name
'Sebbar, Ghizlane'
'Hni, Brahim'
'Hökelek, Tuncer'
'Mague, Joel T.'
'Sebbar, Nada Kheira'
'Belkadi, Bouchra'
'Essassi, El Mokhtar'
_publ_section_title
;
 Crystal structure, Hirshfeld surface analysis and interaction energy, DFT
 and antibacterial activity studies of
 (Z)-4-hexyl-2-(4-methylbenzylidene)-2H-benzo[b][1,4]thiazin-3(4H)-one
;
_journal_coeditor_code           EX2032
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              889
_journal_page_last               895
_journal_paper_doi               10.1107/S205698902000657X
_journal_volume                  76
_journal_year                    2020
_chemical_formula_iupac          'C22 H25 N O S'
_chemical_formula_moiety         'C22 H25 N O S'
_chemical_formula_sum            'C22 H25 N O S'
_chemical_formula_weight         351.49
_chemical_name_systematic
(Z)-4-Hexyl-2-(4-methylbenzylidene)-2H-benzo[b][1,4]thiazin-3(4H)-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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                106.474(3)
_cell_angle_beta                 109.398(3)
_cell_angle_gamma                93.383(3)
_cell_formula_units_Z            2
_cell_length_a                   8.8581(19)
_cell_length_b                   9.183(2)
_cell_length_c                   13.021(3)
_cell_measurement_reflns_used    7052
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      28.6754
_cell_measurement_theta_min      2.4348
_cell_volume                     944.2(4)
_computing_cell_refinement
;
SAINT (Bruker, 2016)
;
_computing_data_collection
;
APEX3 (Bruker, 2016)
;
_computing_data_reduction
;
SAINT (Bruker, 2016)
;
_computing_molecular_graphics
;
DIAMOND (Brandenburg & Putz, 2012)
;
_computing_publication_material
;
SHELXTL (Sheldrick, 2008)
;
_computing_structure_refinement
;
SHELXL2018/3 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT2014/5 (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Bruker Smart APEX CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0287
_diffrn_reflns_av_unetI/netI     0.0352
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            17663
_diffrn_reflns_theta_full        28.000
_diffrn_reflns_theta_max         28.757
_diffrn_reflns_theta_min         1.751
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.181
_exptl_absorpt_correction_T_max  0.98
_exptl_absorpt_correction_T_min  0.83
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Krause et al., 2015)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.236
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             376
_exptl_crystal_size_max          0.332
_exptl_crystal_size_mid          0.264
_exptl_crystal_size_min          0.103
_refine_diff_density_max         0.535
_refine_diff_density_min         -0.216
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         4860
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.077
_refine_ls_R_factor_all          0.0588
_refine_ls_R_factor_gt           0.0460
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0868P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1262
_refine_ls_wR_factor_ref         0.1335
_reflns_number_gt                3807
_reflns_number_total             4860
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ex2032sup1.cif
_cod_data_source_block           I
_cod_database_code               2243403
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.942
_shelx_estimated_absorpt_t_max   0.982
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S S1 0.48853(4) 0.62268(4) 0.80836(3) 0.02689(12) Uani d 1 . .
O O1 0.14092(11) 0.34562(11) 0.54654(8) 0.0296(2) Uani d 1 . .
N N1 0.40988(13) 0.34294(13) 0.59158(9) 0.0230(2) Uani d 1 . .
C C1 0.62657(16) 0.53904(15) 0.74903(11) 0.0238(3) Uani d 1 . .
C C2 0.79091(16) 0.60067(17) 0.80699(13) 0.0295(3) Uani d 1 . .
H H2 0.824726 0.683588 0.877249 0.035 Uiso calc 1 . .
C C3 0.90511(17) 0.54252(18) 0.76340(14) 0.0344(3) Uani d 1 . .
H H3 1.017293 0.583176 0.804334 0.041 Uiso calc 1 . .
C C4 0.85491(18) 0.42485(19) 0.65987(14) 0.0359(4) Uani d 1 . .
H H4 0.932696 0.386664 0.628234 0.043 Uiso calc 1 . .
C C5 0.69171(17) 0.36181(17) 0.60156(13) 0.0304(3) Uani d 1 . .
H H5 0.658838 0.281107 0.530152 0.037 Uiso calc 1 . .
C C6 0.57519(15) 0.41547(15) 0.64649(11) 0.0230(3) Uani d 1 . .
C C7 0.28144(15) 0.41309(15) 0.60267(11) 0.0221(3) Uani d 1 . .
C C8 0.31493(15) 0.57412(15) 0.68247(11) 0.0229(3) Uani d 1 . .
C C9 0.36834(18) 0.18446(15) 0.51035(12) 0.0272(3) Uani d 1 . .
H H9A 0.278067 0.127685 0.519876 0.033 Uiso calc 1 . .
H H9AB 0.463261 0.131943 0.530044 0.033 Uiso calc 1 . .
C C10 0.31894(18) 0.17657(16) 0.38509(12) 0.0292(3) Uani d 1 . .
H H10A 0.222119 0.226310 0.364140 0.035 Uiso calc 1 . .
H H10B 0.408117 0.234298 0.375094 0.035 Uiso calc 1 . .
C C11 0.28073(19) 0.01127(16) 0.30521(12) 0.0321(3) Uani d 1 . .
H H11A 0.381565 -0.033721 0.320101 0.038 Uiso calc 1 . .
H H11B 0.202450 -0.049348 0.323086 0.038 Uiso calc 1 . .
C C12 0.2103(2) -0.00319(18) 0.17853(13) 0.0370(4) Uani d 1 . .
H H12A 0.111018 0.044208 0.164526 0.044 Uiso calc 1 . .
H H12B 0.289671 0.056538 0.160940 0.044 Uiso calc 1 . .
C C13 0.1679(2) -0.1666(2) 0.09621(15) 0.0470(4) Uani d 1 . .
H H13A 0.112018 -0.164616 0.017068 0.056 Uiso calc 1 . .
H H13B 0.090849 -0.227440 0.114929 0.056 Uiso calc 1 . .
C C14 0.3135(3) -0.2469(2) 0.09928(16) 0.0522(5) Uani d 1 . .
H H14A 0.278359 -0.348108 0.039587 0.078 Uiso calc 1 . .
H H14B 0.362499 -0.259934 0.174847 0.078 Uiso calc 1 . .
H H14C 0.393526 -0.184479 0.085374 0.078 Uiso calc 1 . .
C C15 0.20651(16) 0.66746(15) 0.65716(11) 0.0240(3) Uani d 1 . .
H H15 0.112596 0.621988 0.589786 0.029 Uiso calc 1 . .
C C16 0.21350(15) 0.82914(15) 0.71914(11) 0.0237(3) Uani d 1 . .
C C17 0.28006(17) 0.89520(16) 0.83901(11) 0.0270(3) Uani d 1 . .
H H17 0.320387 0.832386 0.885317 0.032 Uiso calc 1 . .
C C18 0.28781(18) 1.05119(16) 0.89087(12) 0.0299(3) Uani d 1 . .
H H18 0.332476 1.093311 0.972370 0.036 Uiso calc 1 . .
C C19 0.23138(17) 1.14756(16) 0.82588(12) 0.0275(3) Uani d 1 . .
C C20 0.16120(18) 1.08124(16) 0.70733(13) 0.0301(3) Uani d 1 . .
H H20 0.119719 1.144064 0.661268 0.036 Uiso calc 1 . .
C C21 0.15056(17) 0.92502(16) 0.65499(12) 0.0287(3) Uani d 1 . .
H H21 0.099424 0.882241 0.573798 0.034 Uiso calc 1 . .
C C22 0.2467(2) 1.31839(17) 0.88163(14) 0.0363(4) Uani d 1 . .
H H22A 0.172104 1.360783 0.827572 0.054 Uiso calc 1 . .
H H22B 0.358422 1.368479 0.902762 0.054 Uiso calc 1 . .
H H22C 0.219515 1.337033 0.950821 0.054 Uiso calc 1 . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C8 S1 C1 . . 99.20(6) ?
C7 N1 C6 . . 124.55(11) ?
C7 N1 C9 . . 115.97(11) ?
C6 N1 C9 . . 119.35(11) ?
C2 C1 C6 . . 120.33(13) ?
C2 C1 S1 . . 117.86(11) ?
C6 C1 S1 . . 121.81(10) ?
C3 C2 C1 . . 120.67(14) ?
C3 C2 H2 . . 119.7 ?
C1 C2 H2 . . 119.7 ?
C4 C3 C2 . . 119.39(14) ?
C4 C3 H3 . . 120.3 ?
C2 C3 H3 . . 120.3 ?
C3 C4 C5 . . 120.51(13) ?
C3 C4 H4 . . 119.7 ?
C5 C4 H4 . . 119.7 ?
C4 C5 C6 . . 120.83(14) ?
C4 C5 H5 . . 119.6 ?
C6 C5 H5 . . 119.6 ?
C5 C6 C1 . . 118.17(12) ?
C5 C6 N1 . . 120.84(12) ?
C1 C6 N1 . . 120.95(12) ?
O1 C7 N1 . . 120.68(12) ?
O1 C7 C8 . . 120.59(11) ?
N1 C7 C8 . . 118.71(11) ?
C15 C8 C7 . . 118.49(12) ?
C15 C8 S1 . . 124.93(10) ?
C7 C8 S1 . . 116.43(9) ?
N1 C9 C10 . . 113.78(11) ?
N1 C9 H9A . . 108.8 ?
C10 C9 H9A . . 108.8 ?
N1 C9 H9AB . . 108.8 ?
C10 C9 H9AB . . 108.8 ?
H9A C9 H9AB . . 107.7 ?
C11 C10 C9 . . 111.74(11) ?
C11 C10 H10A . . 109.3 ?
C9 C10 H10A . . 109.3 ?
C11 C10 H10B . . 109.3 ?
C9 C10 H10B . . 109.3 ?
H10A C10 H10B . . 107.9 ?
C12 C11 C10 . . 113.46(12) ?
C12 C11 H11A . . 108.9 ?
C10 C11 H11A . . 108.9 ?
C12 C11 H11B . . 108.9 ?
C10 C11 H11B . . 108.9 ?
H11A C11 H11B . . 107.7 ?
C13 C12 C11 . . 115.01(14) ?
C13 C12 H12A . . 108.5 ?
C11 C12 H12A . . 108.5 ?
C13 C12 H12B . . 108.5 ?
C11 C12 H12B . . 108.5 ?
H12A C12 H12B . . 107.5 ?
C12 C13 C14 . . 113.96(15) ?
C12 C13 H13A . . 108.8 ?
C14 C13 H13A . . 108.8 ?
C12 C13 H13B . . 108.8 ?
C14 C13 H13B . . 108.8 ?
H13A C13 H13B . . 107.7 ?
C13 C14 H14A . . 109.5 ?
C13 C14 H14B . . 109.5 ?
H14A C14 H14B . . 109.5 ?
C13 C14 H14C . . 109.5 ?
H14A C14 H14C . . 109.5 ?
H14B C14 H14C . . 109.5 ?
C8 C15 C16 . . 128.87(12) ?
C8 C15 H15 . . 115.6 ?
C16 C15 H15 . . 115.6 ?
C21 C16 C17 . . 117.48(12) ?
C21 C16 C15 . . 118.10(12) ?
C17 C16 C15 . . 124.42(12) ?
C18 C17 C16 . . 120.77(12) ?
C18 C17 H17 . . 119.6 ?
C16 C17 H17 . . 119.6 ?
C17 C18 C19 . . 121.36(13) ?
C17 C18 H18 . . 119.3 ?
C19 C18 H18 . . 119.3 ?
C20 C19 C18 . . 117.81(13) ?
C20 C19 C22 . . 120.67(13) ?
C18 C19 C22 . . 121.52(13) ?
C21 C20 C19 . . 121.14(13) ?
C21 C20 H20 . . 119.4 ?
C19 C20 H20 . . 119.4 ?
C20 C21 C16 . . 121.33(13) ?
C20 C21 H21 . . 119.3 ?
C16 C21 H21 . . 119.3 ?
C19 C22 H22A . . 109.5 ?
C19 C22 H22B . . 109.5 ?
H22A C22 H22B . . 109.5 ?
C19 C22 H22C . . 109.5 ?
H22A C22 H22C . . 109.5 ?
H22B C22 H22C . . 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
S1 C8 . 1.7552(13) ?
S1 C1 . 1.7560(14) ?
O1 C7 . 1.2310(15) ?
N1 C7 . 1.3687(17) ?
N1 C6 . 1.4207(17) ?
N1 C9 . 1.4756(17) ?
C1 C2 . 1.3928(19) ?
C1 C6 . 1.3976(19) ?
C2 C3 . 1.380(2) ?
C2 H2 . 0.9500 ?
C3 C4 . 1.379(2) ?
C3 H3 . 0.9500 ?
C4 C5 . 1.387(2) ?
C4 H4 . 0.9500 ?
C5 C6 . 1.3958(19) ?
C5 H5 . 0.9500 ?
C7 C8 . 1.4922(18) ?
C8 C15 . 1.3464(18) ?
C9 C10 . 1.5205(19) ?
C9 H9A . 0.9900 ?
C9 H9AB . 0.9900 ?
C10 C11 . 1.5201(19) ?
C10 H10A . 0.9900 ?
C10 H10B . 0.9900 ?
C11 C12 . 1.520(2) ?
C11 H11A . 0.9900 ?
C11 H11B . 0.9900 ?
C12 C13 . 1.515(2) ?
C12 H12A . 0.9900 ?
C12 H12B . 0.9900 ?
C13 C14 . 1.518(3) ?
C13 H13A . 0.9900 ?
C13 H13B . 0.9900 ?
C14 H14A . 0.9800 ?
C14 H14B . 0.9800 ?
C14 H14C . 0.9800 ?
C15 C16 . 1.4615(18) ?
C15 H15 . 0.9500 ?
C16 C21 . 1.3963(18) ?
C16 C17 . 1.4004(18) ?
C17 C18 . 1.3862(19) ?
C17 H17 . 0.9500 ?
C18 C19 . 1.395(2) ?
C18 H18 . 0.9500 ?
C19 C20 . 1.387(2) ?
C19 C22 . 1.5067(19) ?
C20 C21 . 1.3851(19) ?
C20 H20 . 0.9500 ?
C21 H21 . 0.9500 ?
C22 H22A . 0.9800 ?
C22 H22B . 0.9800 ?
C22 H22C . 0.9800 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
C4 H4 O1 1_655 0.95 2.42 3.349(2) 168 y
C15 H15 O1 2_566 0.95 2.45 3.2977(17) 148 yes
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C8 S1 C1 C2 . . . . 154.11(11) ?
C8 S1 C1 C6 . . . . -25.32(12) ?
C6 C1 C2 C3 . . . . 1.0(2) ?
S1 C1 C2 C3 . . . . -178.44(11) ?
C1 C2 C3 C4 . . . . 1.7(2) ?
C2 C3 C4 C5 . . . . -2.0(2) ?
C3 C4 C5 C6 . . . . -0.3(2) ?
C4 C5 C6 C1 . . . . 2.9(2) ?
C4 C5 C6 N1 . . . . -174.94(13) ?
C2 C1 C6 C5 . . . . -3.2(2) ?
S1 C1 C6 C5 . . . . 176.17(10) ?
C2 C1 C6 N1 . . . . 174.59(12) ?
S1 C1 C6 N1 . . . . -5.99(18) ?
C7 N1 C6 C5 . . . . -156.27(13) ?
C9 N1 C6 C5 . . . . 19.42(18) ?
C7 N1 C6 C1 . . . . 25.95(19) ?
C9 N1 C6 C1 . . . . -158.36(12) ?
C6 N1 C7 O1 . . . . 175.34(12) ?
C9 N1 C7 O1 . . . . -0.48(18) ?
C6 N1 C7 C8 . . . . -3.51(19) ?
C9 N1 C7 C8 . . . . -179.33(11) ?
O1 C7 C8 C15 . . . . -30.00(19) ?
N1 C7 C8 C15 . . . . 148.85(13) ?
O1 C7 C8 S1 . . . . 145.87(11) ?
N1 C7 C8 S1 . . . . -35.27(15) ?
C1 S1 C8 C15 . . . . -139.90(12) ?
C1 S1 C8 C7 . . . . 44.53(11) ?
C7 N1 C9 C10 . . . . 79.89(15) ?
C6 N1 C9 C10 . . . . -96.17(14) ?
N1 C9 C10 C11 . . . . 178.84(12) ?
C9 C10 C11 C12 . . . . 172.66(13) ?
C10 C11 C12 C13 . . . . -178.97(14) ?
C11 C12 C13 C14 . . . . -64.8(2) ?
C7 C8 C15 C16 . . . . -178.20(12) ?
S1 C8 C15 C16 . . . . 6.3(2) ?
C8 C15 C16 C21 . . . . 144.09(15) ?
C8 C15 C16 C17 . . . . -35.5(2) ?
C21 C16 C17 C18 . . . . -2.2(2) ?
C15 C16 C17 C18 . . . . 177.39(13) ?
C16 C17 C18 C19 . . . . -0.6(2) ?
C17 C18 C19 C20 . . . . 2.4(2) ?
C17 C18 C19 C22 . . . . -177.10(14) ?
C18 C19 C20 C21 . . . . -1.3(2) ?
C22 C19 C20 C21 . . . . 178.20(14) ?
C19 C20 C21 C16 . . . . -1.6(2) ?
C17 C16 C21 C20 . . . . 3.3(2) ?
C15 C16 C21 C20 . . . . -176.31(13) ?

_cod_database_fobs_code 2243403
