#------------------------------------------------------------------------------
#$Date: 2025-08-19 21:17:10 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301807 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/24/13/2241371.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_2241371
loop_
_publ_author_name
'Sebbar, N. K.'
'Ellouz, M.'
'Essassi, E. M.'
'Ouzidan, Y.'
'Mague, J. T.'
_publ_section_title
;
 Crystal structure of
 4-benzyl-2H-benzo[b][1,4]thiazin-3(4H)-one
;
_journal_coeditor_code           HB7545
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o999
_journal_paper_doi               10.1107/S2056989015022276
_journal_volume                  71
_journal_year                    2015
_chemical_formula_iupac          'C15 H13 N O S'
_chemical_formula_moiety         'C15 H13 N O S'
_chemical_formula_sum            'C15 H13 N O S'
_chemical_formula_weight         255.32
_chemical_name_systematic
;
4-Benzyl-2H-benzo[b][1,4]thiazin-3(4H)-one
;
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 93.1280(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.8711(7)
_cell_length_b                   5.3815(3)
_cell_length_c                   21.1997(13)
_cell_measurement_reflns_used    9273
_cell_measurement_temperature    150.(2)
_cell_measurement_theta_max      29.0
_cell_measurement_theta_min      2.6
_cell_volume                     1238.39(13)
_computing_cell_refinement
;
SAINT (Bruker, 2015)
;
_computing_data_collection
;
APEX2 (Bruker, 2015)
;
_computing_data_reduction
;
SAINT (Bruker, 2015)
;
_computing_molecular_graphics
;
DIAMOND (Brandenburg & Putz, 2012)
;
_computing_publication_material
;
SHELXTL (Sheldrick, 2015b)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.996
_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  0.0336
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            22588
_diffrn_reflns_theta_full        29.000
_diffrn_reflns_theta_max         29.094
_diffrn_reflns_theta_min         1.876
_exptl_absorpt_coefficient_mu    0.247
_exptl_absorpt_correction_T_max  0.96
_exptl_absorpt_correction_T_min  0.88
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2015)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.369
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.310
_exptl_crystal_size_mid          0.186
_exptl_crystal_size_min          0.154
_refine_diff_density_max         0.431
_refine_diff_density_min         -0.188
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         3318
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0453
_refine_ls_R_factor_gt           0.0375
_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/[σ²(Fo²)+(0.0711P)²+0.0734P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1034
_refine_ls_wR_factor_ref         0.1069
_reflns_number_gt                2731
_reflns_number_total             3318
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            hb7545sup1.cif
_cod_data_source_block           I
_cod_database_code               2241371
_cod_database_fobs_code          2241371
_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   0.927
_shelx_estimated_absorpt_t_max   0.963
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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
S S1 1.01122(3) 0.51867(6) 0.64271(2) 0.02520(11) Uani d 1
O O1 0.82014(8) 0.06255(17) 0.72781(4) 0.0263(2) Uani d 1
N N1 0.77044(9) 0.22455(18) 0.63087(4) 0.0188(2) Uani d 1
C C1 0.78669(10) 0.4044(2) 0.58307(5) 0.0183(2) Uani d 1
C C2 0.69629(11) 0.4345(2) 0.53375(5) 0.0228(2) Uani d 1
H H2 0.6216 0.3430 0.5342 0.027 Uiso calc 1
C C3 0.71505(12) 0.5966(2) 0.48439(5) 0.0266(3) Uani d 1
H H3 0.6537 0.6136 0.4510 0.032 Uiso calc 1
C C4 0.82274(12) 0.7341(2) 0.48348(5) 0.0283(3) Uani d 1
H H4 0.8359 0.8435 0.4493 0.034 Uiso calc 1
C C5 0.91096(12) 0.7109(3) 0.53267(5) 0.0273(3) Uani d 1
H H5 0.9839 0.8080 0.5325 0.033 Uiso calc 1
C C6 0.89443(10) 0.5470(2) 0.58242(5) 0.0204(2) Uani d 1
C C7 0.90903(11) 0.4571(2) 0.70494(5) 0.0202(2) Uani d 1
H H7A 0.9579 0.4299 0.7451 0.024 Uiso calc 1
H H7B 0.8549 0.6026 0.7104 0.024 Uiso calc 1
C C8 0.83135(10) 0.2310(2) 0.68959(5) 0.0191(2) Uani d 1
C C9 0.68427(11) 0.0192(2) 0.61862(6) 0.0206(2) Uani d 1
H H9A 0.7166 -0.1296 0.6415 0.025 Uiso calc 1
H H9B 0.6814 -0.0193 0.5729 0.025 Uiso calc 1
C C10 0.55414(10) 0.0666(2) 0.63773(5) 0.0185(2) Uani d 1
C C11 0.52211(11) 0.2662(2) 0.67490(5) 0.0239(3) Uani d 1
H H11 0.5828 0.3854 0.6879 0.029 Uiso calc 1
C C12 0.40231(12) 0.2935(3) 0.69330(5) 0.0290(3) Uani d 1
H H12 0.3813 0.4312 0.7186 0.035 Uiso calc 1
C C13 0.31340(12) 0.1201(3) 0.67478(6) 0.0302(3) Uani d 1
H H13 0.2314 0.1387 0.6874 0.036 Uiso calc 1
C C14 0.34421(12) -0.0800(3) 0.63797(7) 0.0319(3) Uani d 1
H H14 0.2835 -0.1998 0.6255 0.038 Uiso calc 1
C C15 0.46353(11) -0.1061(2) 0.61924(6) 0.0261(3) Uani d 1
H H15 0.4839 -0.2430 0.5935 0.031 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
C6 S1 C7 95.66(5)
C8 N1 C1 123.74(9)
C8 N1 C9 116.79(9)
C1 N1 C9 119.46(9)
C6 C1 C2 118.72(10)
C6 C1 N1 121.15(9)
C2 C1 N1 120.07(10)
C3 C2 C1 120.60(11)
C3 C2 H2 119.7
C1 C2 H2 119.7
C4 C3 C2 120.38(11)
C4 C3 H3 119.8
C2 C3 H3 119.8
C5 C4 C3 119.52(11)
C5 C4 H4 120.2
C3 C4 H4 120.2
C4 C5 C6 121.00(12)
C4 C5 H5 119.5
C6 C5 H5 119.5
C5 C6 C1 119.76(10)
C5 C6 S1 119.15(9)
C1 C6 S1 121.08(9)
C8 C7 S1 110.56(8)
C8 C7 H7A 109.5
S1 C7 H7A 109.5
C8 C7 H7B 109.5
S1 C7 H7B 109.5
H7A C7 H7B 108.1
O1 C8 N1 121.21(10)
O1 C8 C7 121.93(10)
N1 C8 C7 116.84(9)
N1 C9 C10 115.07(9)
N1 C9 H9A 108.5
C10 C9 H9A 108.5
N1 C9 H9B 108.5
C10 C9 H9B 108.5
H9A C9 H9B 107.5
C11 C10 C15 118.70(11)
C11 C10 C9 123.32(10)
C15 C10 C9 117.92(10)
C12 C11 C10 120.65(12)
C12 C11 H11 119.7
C10 C11 H11 119.7
C13 C12 C11 120.02(12)
C13 C12 H12 120.0
C11 C12 H12 120.0
C14 C13 C12 119.89(12)
C14 C13 H13 120.1
C12 C13 H13 120.1
C13 C14 C15 120.04(12)
C13 C14 H14 120.0
C15 C14 H14 120.0
C14 C15 C10 120.69(12)
C14 C15 H15 119.7
C10 C15 H15 119.7
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 C6 1.7583(11)
S1 C7 1.8013(12)
O1 C8 1.2262(14)
N1 C8 1.3781(13)
N1 C1 1.4191(14)
N1 C9 1.4628(14)
C1 C6 1.4012(16)
C1 C2 1.4047(15)
C2 C3 1.3860(18)
C2 H2 0.9500
C3 C4 1.3859(19)
C3 H3 0.9500
C4 C5 1.3833(16)
C4 H4 0.9500
C5 C6 1.3940(17)
C5 H5 0.9500
C7 C8 1.5066(16)
C7 H7A 0.9900
C7 H7B 0.9900
C9 C10 1.5144(16)
C9 H9A 0.9900
C9 H9B 0.9900
C10 C11 1.3880(16)
C10 C15 1.3947(16)
C11 C12 1.3876(17)
C11 H11 0.9500
C12 C13 1.3848(19)
C12 H12 0.9500
C13 C14 1.382(2)
C13 H13 0.9500
C14 C15 1.3843(18)
C14 H14 0.9500
C15 H15 0.9500
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
C7 H7A O1 2_756 0.99 2.55 3.2504(14) 128
C7 H7B O1 1_565 0.99 2.53 3.4403(15) 152
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
C8 N1 C1 C6 23.43(16)
C9 N1 C1 C6 -156.89(11)
C8 N1 C1 C2 -159.32(11)
C9 N1 C1 C2 20.36(15)
C6 C1 C2 C3 1.99(17)
N1 C1 C2 C3 -175.32(11)
C1 C2 C3 C4 -0.93(19)
C2 C3 C4 C5 -0.81(19)
C3 C4 C5 C6 1.48(19)
C4 C5 C6 C1 -0.40(19)
C4 C5 C6 S1 178.35(10)
C2 C1 C6 C5 -1.33(17)
N1 C1 C6 C5 175.96(11)
C2 C1 C6 S1 179.95(9)
N1 C1 C6 S1 -2.77(15)
C7 S1 C6 C5 147.46(11)
C7 S1 C6 C1 -33.80(10)
C6 S1 C7 C8 57.87(9)
C1 N1 C8 O1 -175.23(10)
C9 N1 C8 O1 5.09(15)
C1 N1 C8 C7 6.40(15)
C9 N1 C8 C7 -173.29(10)
S1 C7 C8 O1 131.04(10)
S1 C7 C8 N1 -50.60(12)
C8 N1 C9 C10 88.08(12)
C1 N1 C9 C10 -91.62(12)
N1 C9 C10 C11 -12.01(16)
N1 C9 C10 C15 170.98(10)
C15 C10 C11 C12 0.00(17)
C9 C10 C11 C12 -176.99(11)
C10 C11 C12 C13 0.24(18)
C11 C12 C13 C14 0.01(18)
C12 C13 C14 C15 -0.51(19)
C13 C14 C15 C10 0.75(19)
C11 C10 C15 C14 -0.49(18)
C9 C10 C15 C14 176.66(11)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 901091
