#------------------------------------------------------------------------------
#$Date: 2020-04-08 08:26:22 +0300 (Wed, 08 Apr 2020) $
#$Revision: 250492 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/24/33/2243352.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_2243352
loop_
_publ_author_name
'Sebbar, Ghizlane'
'Mohamed, Ellouz'
'Hökelek, Tuncer'
'Mague, Joel T.'
'Sebbar, Nada Kheira'
'Essassi, El Mokhtar'
'Belkadi, Bouchra'
_publ_section_title
;
 Crystal structure, Hirshfeld surface analysis and interaction energy, DFT
 and antibacterial activity studies of ethyl
 2-[(2Z)-2-(2-chlorobenzylidene)-3-oxo-3,4-dihydro-2H-1,4-benzothiazin-4-yl]acetate
;
_journal_coeditor_code           LH5950
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              629
_journal_page_last               636
_journal_paper_doi               10.1107/S2056989020004119
_journal_volume                  76
_journal_year                    2020
_chemical_formula_iupac          'C19 H16 Cl N O3 S'
_chemical_formula_moiety         'C19 H16 Cl N O3 S'
_chemical_formula_sum            'C19 H16 Cl N O3 S'
_chemical_formula_weight         373.84
_chemical_name_systematic
;
Ethyl
2-[(2Z)-2-(2-chlorobenzylidene)-3-oxo-3,4-dihydro-2H-\
1,4-benzothiazin-4-yl]acetate
;
_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'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     'dual space'
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 105.1050(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.6882(2)
_cell_length_b                   9.0903(2)
_cell_length_c                   16.9533(3)
_cell_measurement_reflns_used    9820
_cell_measurement_temperature    150.(2)
_cell_measurement_theta_max      74.5619
_cell_measurement_theta_min      3.9174
_cell_volume                     1739.04(6)
_computing_cell_refinement
;
SAINT (Bruker, 2016)
;
_computing_data_collection
;
APEX3 (Bruker, 2016)
;
_computing_data_reduction
;
SAINT (Bruker, 2016), CELL_NOW (Sheldrick, 2008a)
;
_computing_molecular_graphics
;
DIAMOND (Brandenburg & Putz, 2012)
;
_computing_publication_material
;
SHELXTL (Sheldrick, 2008b)
;
_computing_structure_refinement
;
SHELXL2018 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 10.4167
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type  'Bruker D8 VENTURE PHOTON 100 CMOS'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0319
_diffrn_reflns_av_unetI/netI     0.0479
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            25761
_diffrn_reflns_theta_full        70.000
_diffrn_reflns_theta_max         74.554
_diffrn_reflns_theta_min         3.917
_diffrn_source                   'INCOATEC I\mS micro--focus source'
_exptl_absorpt_coefficient_mu    3.223
_exptl_absorpt_correction_T_max  0.72
_exptl_absorpt_correction_T_min  0.57
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(TWINABS; Sheldrick, 2009)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.428
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             776
_exptl_crystal_size_max          0.193
_exptl_crystal_size_mid          0.151
_exptl_crystal_size_min          0.109
_refine_diff_density_max         0.723
_refine_diff_density_min         -0.804
_refine_ls_extinction_coef       0.0032(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method
;
SHELXL2018/1 (Sheldrick, 2015b)
;
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     292
_refine_ls_number_reflns         25761
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.025
_refine_ls_R_factor_all          0.0480
_refine_ls_R_factor_gt           0.0394
_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/[σ²(Fo²)+(0.0405P)²+0.4043P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0953
_refine_ls_wR_factor_ref         0.1014
_reflns_number_gt                21950
_reflns_number_total             25761
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            lh5950sup1.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2243352
_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   0.575
_shelx_estimated_absorpt_t_max   0.720
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
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl Cl1 0.50488(5) 0.51497(7) 0.19568(3) 0.03952(18) Uani d 1 . .
S S1 0.44083(4) 0.78070(6) 0.47131(3) 0.02735(16) Uani d 1 . .
O O1 0.31103(13) 0.39288(15) 0.41536(8) 0.0264(3) Uani d 1 . .
O O2 0.05392(14) 0.49512(17) 0.29883(9) 0.0341(4) Uani d 1 . .
O O3 -0.04896(13) 0.37965(16) 0.37586(9) 0.0306(3) Uani d 1 . .
N N1 0.21745(14) 0.60019(17) 0.43805(10) 0.0223(3) Uani d 1 . .
C C1 0.19875(18) 0.7541(2) 0.42964(11) 0.0216(4) Uani d 1 . .
C C2 0.08488(19) 0.8137(2) 0.40863(13) 0.0272(4) Uani d 1 . .
H H2 0.019(2) 0.750(3) 0.3964(15) 0.032(6) Uiso d 1 . .
C C3 0.0683(2) 0.9646(2) 0.40245(13) 0.0299(5) Uani d 1 . .
H H3 -0.010(3) 1.002(3) 0.3866(16) 0.038(7) Uiso d 1 . .
C C4 0.1643(2) 1.0587(2) 0.41608(13) 0.0294(5) Uani d 1 . .
H H4 0.152(3) 1.159(3) 0.4110(17) 0.045(7) Uiso d 1 . .
C C5 0.2778(2) 1.0009(2) 0.43568(13) 0.0274(4) Uani d 1 . .
H H5 0.345(2) 1.066(3) 0.4429(15) 0.033(6) Uiso d 1 . .
C C6 0.29556(17) 0.8496(2) 0.44327(11) 0.0228(4) Uani d 1 . .
C C7 0.41573(18) 0.6168(2) 0.41447(11) 0.0224(4) Uani d 1 . .
C C8 0.31254(18) 0.5270(2) 0.42214(11) 0.0214(4) Uani d 1 . .
C C9 0.48358(18) 0.5650(2) 0.36782(12) 0.0239(4) Uani d 1 . .
H H9 0.461(2) 0.474(3) 0.3411(15) 0.030(6) Uiso d 1 . .
C C10 0.58341(18) 0.6384(2) 0.34694(12) 0.0230(4) Uani d 1 . .
C C11 0.59934(19) 0.6260(2) 0.26787(12) 0.0266(4) Uani d 1 . .
C C12 0.6869(2) 0.7022(2) 0.24392(13) 0.0308(5) Uani d 1 . .
H H12 0.693(2) 0.689(3) 0.1896(16) 0.039(7) Uiso d 1 . .
C C13 0.7644(2) 0.7914(2) 0.29922(13) 0.0316(5) Uani d 1 . .
H H13 0.826(3) 0.842(3) 0.2818(17) 0.042(7) Uiso d 1 . .
C C14 0.75389(19) 0.8019(2) 0.37885(13) 0.0281(4) Uani d 1 . .
H H14 0.808(2) 0.863(3) 0.4187(16) 0.037(7) Uiso d 1 . .
C C15 0.66479(18) 0.7271(2) 0.40190(12) 0.0255(4) Uani d 1 . .
H H15 0.659(2) 0.733(2) 0.4564(15) 0.027(6) Uiso d 1 . .
C C16 0.11979(18) 0.5077(2) 0.44607(12) 0.0235(4) Uani d 1 . .
H H16A 0.151(2) 0.421(3) 0.4763(15) 0.029(6) Uiso d 1 . .
H H16B 0.077(2) 0.556(3) 0.4769(14) 0.026(6) Uiso d 1 . .
C C17 0.03970(18) 0.4622(2) 0.36420(12) 0.0244(4) Uani d 1 . .
C C18 -0.1348(2) 0.3263(3) 0.30254(15) 0.0386(5) Uani d 1 . .
H H18A -0.092(3) 0.255(3) 0.2763(18) 0.048(8) Uiso d 1 . .
H H18B -0.161(3) 0.410(3) 0.2641(19) 0.049(8) Uiso d 1 . .
C C19 -0.2350(3) 0.2585(4) 0.3297(2) 0.0509(7) Uani d 1 . .
H H19A -0.205(3) 0.173(3) 0.370(2) 0.054(8) Uiso d 1 . .
H H19B -0.289(3) 0.220(4) 0.283(2) 0.069(10) Uiso d 1 . .
H H19C -0.274(3) 0.331(4) 0.359(2) 0.061(9) Uiso d 1 . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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
C6 S1 C7 . . 98.19(9) ?
C17 O3 C18 . . 116.60(16) ?
C8 N1 C1 . . 124.52(15) ?
C8 N1 C16 . . 115.56(16) ?
C1 N1 C16 . . 118.47(16) ?
C2 C1 C6 . . 118.60(18) ?
C2 C1 N1 . . 121.41(17) ?
C6 C1 N1 . . 120.00(17) ?
C3 C2 C1 . . 120.63(19) ?
C3 C2 H2 . . 120.0(15) ?
C1 C2 H2 . . 119.4(15) ?
C4 C3 C2 . . 120.6(2) ?
C4 C3 H3 . . 120.2(16) ?
C2 C3 H3 . . 119.2(16) ?
C3 C4 C5 . . 119.4(2) ?
C3 C4 H4 . . 120.0(18) ?
C5 C4 H4 . . 120.6(18) ?
C4 C5 C6 . . 120.5(2) ?
C4 C5 H5 . . 119.4(15) ?
C6 C5 H5 . . 120.1(15) ?
C5 C6 C1 . . 120.27(18) ?
C5 C6 S1 . . 119.21(15) ?
C1 C6 S1 . . 120.51(15) ?
C9 C7 C8 . . 118.34(17) ?
C9 C7 S1 . . 125.50(16) ?
C8 C7 S1 . . 116.11(14) ?
O1 C8 N1 . . 120.36(17) ?
O1 C8 C7 . . 121.99(17) ?
N1 C8 C7 . . 117.64(16) ?
C7 C9 C10 . . 127.75(19) ?
C7 C9 H9 . . 116.7(15) ?
C10 C9 H9 . . 115.3(15) ?
C15 C10 C11 . . 116.42(18) ?
C15 C10 C9 . . 123.16(17) ?
C11 C10 C9 . . 120.39(18) ?
C12 C11 C10 . . 122.19(19) ?
C12 C11 Cl1 . . 117.82(16) ?
C10 C11 Cl1 . . 119.98(16) ?
C11 C12 C13 . . 119.92(19) ?
C11 C12 H12 . . 118.0(16) ?
C13 C12 H12 . . 122.0(16) ?
C12 C13 C14 . . 119.4(2) ?
C12 C13 H13 . . 118.8(16) ?
C14 C13 H13 . . 121.8(16) ?
C15 C14 C13 . . 120.3(2) ?
C15 C14 H14 . . 119.2(16) ?
C13 C14 H14 . . 120.5(16) ?
C14 C15 C10 . . 121.74(18) ?
C14 C15 H15 . . 120.3(15) ?
C10 C15 H15 . . 118.0(15) ?
N1 C16 C17 . . 112.65(16) ?
N1 C16 H16A . . 109.1(15) ?
C17 C16 H16A . . 109.0(14) ?
N1 C16 H16B . . 109.1(15) ?
C17 C16 H16B . . 110.8(15) ?
H16A C16 H16B . . 106(2) ?
O2 C17 O3 . . 125.18(19) ?
O2 C17 C16 . . 125.21(18) ?
O3 C17 C16 . . 109.61(16) ?
O3 C18 C19 . . 107.0(2) ?
O3 C18 H18A . . 106.6(17) ?
C19 C18 H18A . . 113.0(17) ?
O3 C18 H18B . . 109.1(17) ?
C19 C18 H18B . . 112.6(18) ?
H18A C18 H18B . . 108(2) ?
C18 C19 H19A . . 111.0(18) ?
C18 C19 H19B . . 108(2) ?
H19A C19 H19B . . 109(3) ?
C18 C19 H19C . . 112.1(19) ?
H19A C19 H19C . . 107(2) ?
H19B C19 H19C . . 111(3) ?
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
Cl1 C11 . 1.741(2) ?
S1 C6 . 1.755(2) ?
S1 C7 . 1.757(2) ?
O1 C8 . 1.224(2) ?
O2 C17 . 1.200(2) ?
O3 C17 . 1.335(2) ?
O3 C18 . 1.462(3) ?
N1 C8 . 1.381(2) ?
N1 C1 . 1.417(2) ?
N1 C16 . 1.452(2) ?
C1 C2 . 1.395(3) ?
C1 C6 . 1.397(3) ?
C2 C3 . 1.386(3) ?
C2 H2 . 0.95(3) ?
C3 C4 . 1.382(3) ?
C3 H3 . 0.94(3) ?
C4 C5 . 1.384(3) ?
C4 H4 . 0.93(3) ?
C5 C6 . 1.392(3) ?
C5 H5 . 0.96(3) ?
C7 C9 . 1.343(3) ?
C7 C8 . 1.490(3) ?
C9 C10 . 1.465(3) ?
C9 H9 . 0.95(2) ?
C10 C15 . 1.401(3) ?
C10 C11 . 1.405(3) ?
C11 C12 . 1.382(3) ?
C12 C13 . 1.383(3) ?
C12 H12 . 0.95(3) ?
C13 C14 . 1.390(3) ?
C13 H13 . 0.96(3) ?
C14 C15 . 1.382(3) ?
C14 H14 . 0.97(3) ?
C15 H15 . 0.95(2) ?
C16 C17 . 1.515(3) ?
C16 H16A . 0.96(3) ?
C16 H16B . 0.92(3) ?
C18 C19 . 1.498(4) ?
C18 H18A . 0.99(3) ?
C18 H18B . 1.00(3) ?
C19 H19A . 1.03(3) ?
C19 H19B . 0.94(4) ?
C19 H19C . 1.00(4) ?
loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
_geom_contact_publ_flag
Cl1 C14 3.5363(9) . 2_645 yes
Cl1 S1 3.7268(3) . 2_645 yes
Cl1 C10 3.5940(7) . 2_645 yes
Cl1 C15 3.4359(7) . 2_645 yes
Cl1 H9 2.674(8) . . yes
S1 N1 3.0100(6) . . yes
S1 C15 3.1748(8) . . yes
S1 O1 3.4189(6) . 3_666 yes
S1 H15 2.660(10) . . yes
S1 H5 2.906(9) . 3_676 yes
O1 C17 3.1263(9) . . yes
O1 C12 3.2141(10) . 2_645 yes
O1 C15 3.2268(8) . 3_666 yes
O2 N1 2.7902(7) . . yes
O2 C8 3.2091(9) . . yes
O2 C1 3.3715(8) . . yes
O2 C3 3.3498(10) . 2_545 yes
O2 C2 3.4103(9) . . yes
O1 H9 2.516(9) . . yes
O1 H16A 2.376(9) . . yes
O1 H4 2.806(11) . 1_545 yes
O1 H12 2.560(9) . 2_645 yes
O1 H15 2.400(8) . 3_666 yes
O2 H18B 2.545(11) . . yes
O2 H13 2.606(10) . 2_645 yes
O2 H18A 2.74(3) . . yes
O3 H16B 2.666(8) . 3_566 yes
C2 C17 3.2932(10) . . yes
C4 C14 3.5882(12) . 3_676 yes
C2 H16B 2.621(8) . . yes
C4 H14 2.826(10) . 3_676 yes
C4 H12 2.993(10) . 2_655 yes
C5 H12 2.817(10) . 2_655 yes
C7 H15 2.937(9) . . yes
C15 H16A 2.900(9) . 3_666 yes
C16 H16B 2.987(9) . 3_566 yes
C16 H2 2.538(9) . . yes
C17 H2 2.696(9) . . yes
H2 H16B 2.223(12) . . yes
H5 H12 2.444(13) . 2_655 yes
H5 H15 2.509(12) . 3_676 yes
H16B H16B 2.381(13) . 3_566 yes
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
C12 H12 O1 2_655 0.95(3) 2.56(3) 3.214(2) 126(2) yes
C15 H15 O1 3_666 0.95(2) 2.40(2) 3.227(2) 145.8(15) 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 N1 C1 C2 . . . . 149.38(19) ?
C16 N1 C1 C2 . . . . -16.2(3) ?
C8 N1 C1 C6 . . . . -31.3(3) ?
C16 N1 C1 C6 . . . . 163.13(17) ?
C6 C1 C2 C3 . . . . -0.8(3) ?
N1 C1 C2 C3 . . . . 178.55(18) ?
C1 C2 C3 C4 . . . . 0.8(3) ?
C2 C3 C4 C5 . . . . 0.3(3) ?
C3 C4 C5 C6 . . . . -1.3(3) ?
C4 C5 C6 C1 . . . . 1.2(3) ?
C4 C5 C6 S1 . . . . -178.03(16) ?
C2 C1 C6 C5 . . . . -0.2(3) ?
N1 C1 C6 C5 . . . . -179.53(17) ?
C2 C1 C6 S1 . . . . 179.07(15) ?
N1 C1 C6 S1 . . . . -0.3(2) ?
C7 S1 C6 C5 . . . . -146.23(16) ?
C7 S1 C6 C1 . . . . 34.53(17) ?
C6 S1 C7 C9 . . . . 134.12(18) ?
C6 S1 C7 C8 . . . . -48.28(16) ?
C1 N1 C8 O1 . . . . -165.71(18) ?
C16 N1 C8 O1 . . . . 0.3(3) ?
C1 N1 C8 C7 . . . . 14.8(3) ?
C16 N1 C8 C7 . . . . -179.20(16) ?
C9 C7 C8 O1 . . . . 27.9(3) ?
S1 C7 C8 O1 . . . . -149.91(15) ?
C9 C7 C8 N1 . . . . -152.68(18) ?
S1 C7 C8 N1 . . . . 29.5(2) ?
C8 C7 C9 C10 . . . . 175.30(18) ?
S1 C7 C9 C10 . . . . -7.1(3) ?
C7 C9 C10 C15 . . . . 37.4(3) ?
C7 C9 C10 C11 . . . . -140.4(2) ?
C15 C10 C11 C12 . . . . -2.9(3) ?
C9 C10 C11 C12 . . . . 175.1(2) ?
C15 C10 C11 Cl1 . . . . 178.57(15) ?
C9 C10 C11 Cl1 . . . . -3.5(3) ?
C10 C11 C12 C13 . . . . 1.7(3) ?
Cl1 C11 C12 C13 . . . . -179.76(18) ?
C11 C12 C13 C14 . . . . 0.7(3) ?
C12 C13 C14 C15 . . . . -1.8(3) ?
C13 C14 C15 C10 . . . . 0.5(3) ?
C11 C10 C15 C14 . . . . 1.8(3) ?
C9 C10 C15 C14 . . . . -176.10(19) ?
C8 N1 C16 C17 . . . . -80.3(2) ?
C1 N1 C16 C17 . . . . 86.5(2) ?
C18 O3 C17 O2 . . . . -0.1(3) ?
C18 O3 C17 C16 . . . . -179.95(18) ?
N1 C16 C17 O2 . . . . 1.2(3) ?
N1 C16 C17 O3 . . . . -179.02(16) ?
C17 O3 C18 C19 . . . . -171.0(2) ?

_cod_database_fobs_code 2243352
