#------------------------------------------------------------------------------
#$Date: 2016-05-14 04:45:21 +0300 (Sat, 14 May 2016) $
#$Revision: 182949 $
#$URL: svn://www.crystallography.net/cod/cif/1/54/33/1543318.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_1543318
loop_
_publ_author_name
'Ellouz, Mohamed'
'Sebbar, Nada Kheira'
'Essassi, El Mokhtar'
'Ouzidan, Younes'
'Mague, Joel T.'
'Zouihri, Hafid'
_publ_section_title
;
 4-Benzyl-2-(4-chlorobenzylidene)-3,4-dihydro-2H-1,4-benzothiazin-3(4H)-one
;
_journal_coeditor_code           TK4010
_journal_issue                   5
_journal_name_full               IUCrData
_journal_page_first              x160764
_journal_paper_doi               10.1107/S2414314616007641
_journal_volume                  1
_journal_year                    2016
_chemical_formula_iupac          'C22 H16 Cl N O S'
_chemical_formula_moiety         'C22 H16 Cl N O S'
_chemical_formula_sum            'C22 H16 Cl N O S'
_chemical_formula_weight         377.87
_chemical_name_systematic
(2Z)-4-Benzyl-[(4-chlorophenyl)methylidene]-3,4-dihydro-2H-1,4-benzothiazin-3(4H)-one
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 93.2390(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.8931(11)
_cell_length_b                   6.5358(6)
_cell_length_c                   22.817(2)
_cell_measurement_reflns_used    9932
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      29.1025
_cell_measurement_theta_min      3.1016
_cell_volume                     1770.8(3)
_computing_cell_refinement
;
SAINT (Bruker, 2016)
;
_computing_data_collection
;
APEX3 (Bruker, 2016)
;
_computing_data_reduction
;
SAINT (Bruker, 2016)
;
_computing_molecular_graphics
;
PLATON (Spek, 2009)
;
_computing_publication_material
;
publCIF (Westrip, 2010)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015a)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015)
;
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_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  0.0466
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            32976
_diffrn_reflns_theta_full        29.100
_diffrn_reflns_theta_max         29.177
_diffrn_reflns_theta_min         1.788
_exptl_absorpt_coefficient_mu    0.345
_exptl_absorpt_correction_T_max  0.96
_exptl_absorpt_correction_T_min  0.84
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2016)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.417
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       column
_exptl_crystal_F_000             784
_exptl_crystal_size_max          0.330
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.130
_refine_diff_density_max         1.007
_refine_diff_density_min         -0.467
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.120
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         4771
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.120
_refine_ls_R_factor_all          0.0552
_refine_ls_R_factor_gt           0.0437
_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)+(0.0782P)²+0.0974P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1278
_refine_ls_wR_factor_ref         0.1321
_reflns_number_gt                3718
_reflns_number_total             4771
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            tk4010sup1.cif
_cod_data_source_block           I
_cod_original_cell_volume        1770.7(3)
_cod_database_code               1543318
_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   0.895
_shelx_estimated_absorpt_t_max   0.957
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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
Cl Cl1 0.15276(4) -0.28012(7) 0.65534(2) 0.03513(14) Uani d 1
S S1 0.46828(4) 0.63594(7) 0.70652(2) 0.02992(13) Uani d 1
O O1 0.53363(10) 0.75024(19) 0.54228(5) 0.0313(3) Uani d 1
N N1 0.57084(10) 0.9526(2) 0.62091(5) 0.0209(3) Uani d 1
C C1 0.54418(13) 0.8579(2) 0.72363(7) 0.0224(3) Uani d 1
C C2 0.56174(14) 0.8979(3) 0.78364(7) 0.0283(4) Uani d 1
H H2 0.5347 0.8045 0.8115 0.034 Uiso calc 1
C C3 0.61815(15) 1.0723(3) 0.80268(8) 0.0327(4) Uani d 1
H H3 0.6295 1.0995 0.8435 0.039 Uiso calc 1
C C4 0.65809(14) 1.2075(3) 0.76201(8) 0.0321(4) Uani d 1
H H4 0.6965 1.3282 0.7749 0.039 Uiso calc 1
C C5 0.64220(13) 1.1672(3) 0.70240(8) 0.0264(3) Uani d 1
H H5 0.6708 1.2603 0.6749 0.032 Uiso calc 1
C C6 0.58483(12) 0.9922(2) 0.68203(7) 0.0211(3) Uani d 1
C C7 0.52600(13) 0.7785(2) 0.59501(7) 0.0218(3) Uani d 1
C C8 0.46567(12) 0.6241(2) 0.63034(7) 0.0207(3) Uani d 1
C C9 0.40940(13) 0.4769(2) 0.59899(7) 0.0221(3) Uani d 1
H H9 0.4121 0.4924 0.5577 0.026 Uiso calc 1
C C10 0.34533(12) 0.2989(2) 0.61653(7) 0.0218(3) Uani d 1
C C11 0.33017(14) 0.2371(3) 0.67448(7) 0.0265(3) Uani d 1
H H11 0.3612 0.3173 0.7061 0.032 Uiso calc 1
C C12 0.27024(14) 0.0599(3) 0.68625(7) 0.0275(4) Uani d 1
H H12 0.2598 0.0205 0.7256 0.033 Uiso calc 1
C C13 0.22615(13) -0.0581(3) 0.64020(8) 0.0255(3) Uani d 1
C C14 0.24071(14) -0.0036(3) 0.58230(7) 0.0281(4) Uani d 1
H H14 0.2109 -0.0866 0.5510 0.034 Uiso calc 1
C C15 0.29934(14) 0.1733(3) 0.57106(7) 0.0265(3) Uani d 1
H H15 0.3089 0.2115 0.5315 0.032 Uiso calc 1
C C16 0.60272(13) 1.1156(2) 0.58024(7) 0.0246(3) Uani d 1
H H16A 0.5719 1.2466 0.5940 0.029 Uiso calc 1
H H16B 0.5658 1.0866 0.5411 0.029 Uiso calc 1
C C17 0.72728(13) 1.1438(2) 0.57301(7) 0.0222(3) Uani d 1
C C18 0.80536(14) 0.9877(3) 0.58319(7) 0.0292(4) Uani d 1
H H18 0.7813 0.8574 0.5960 0.035 Uiso calc 1
C C19 0.91849(15) 1.0220(3) 0.57456(8) 0.0366(4) Uani d 1
H H19 0.9716 0.9148 0.5815 0.044 Uiso calc 1
C C20 0.95450(16) 1.2124(3) 0.55586(9) 0.0393(5) Uani d 1
H H20 1.0321 1.2363 0.5505 0.047 Uiso calc 1
C C21 0.87698(16) 1.3658(3) 0.54511(8) 0.0363(4) Uani d 1
H H21 0.9011 1.4954 0.5317 0.044 Uiso calc 1
C C22 0.76351(15) 1.3329(3) 0.55370(7) 0.0289(4) Uani d 1
H H22 0.7106 1.4401 0.5463 0.035 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'
Cl Cl 0.1484 0.1585 '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
C8 S1 C1 103.94(7)
C7 N1 C6 126.48(13)
C7 N1 C16 115.70(13)
C6 N1 C16 117.77(13)
C2 C1 C6 120.57(15)
C2 C1 S1 114.98(13)
C6 C1 S1 124.44(12)
C3 C2 C1 120.39(16)
C3 C2 H2 119.8
C1 C2 H2 119.8
C2 C3 C4 119.67(16)
C2 C3 H3 120.2
C4 C3 H3 120.2
C3 C4 C5 120.20(17)
C3 C4 H4 119.9
C5 C4 H4 119.9
C4 C5 C6 121.19(16)
C4 C5 H5 119.4
C6 C5 H5 119.4
C5 C6 C1 117.97(15)
C5 C6 N1 120.27(14)
C1 C6 N1 121.75(14)
O1 C7 N1 119.88(14)
O1 C7 C8 119.37(14)
N1 C7 C8 120.74(13)
C9 C8 C7 115.58(14)
C9 C8 S1 122.72(12)
C7 C8 S1 121.71(11)
C8 C9 C10 132.25(15)
C8 C9 H9 113.9
C10 C9 H9 113.9
C11 C10 C15 117.47(15)
C11 C10 C9 125.75(15)
C15 C10 C9 116.71(14)
C12 C11 C10 120.96(16)
C12 C11 H11 119.5
C10 C11 H11 119.5
C13 C12 C11 119.55(15)
C13 C12 H12 120.2
C11 C12 H12 120.2
C12 C13 C14 121.19(15)
C12 C13 Cl1 119.19(13)
C14 C13 Cl1 119.61(13)
C15 C14 C13 118.84(16)
C15 C14 H14 120.6
C13 C14 H14 120.6
C14 C15 C10 121.99(15)
C14 C15 H15 119.0
C10 C15 H15 119.0
N1 C16 C17 116.41(13)
N1 C16 H16A 108.2
C17 C16 H16A 108.2
N1 C16 H16B 108.2
C17 C16 H16B 108.2
H16A C16 H16B 107.3
C22 C17 C18 119.32(15)
C22 C17 C16 117.84(14)
C18 C17 C16 122.81(15)
C19 C18 C17 120.08(17)
C19 C18 H18 120.0
C17 C18 H18 120.0
C18 C19 C20 120.35(17)
C18 C19 H19 119.8
C20 C19 H19 119.8
C21 C20 C19 119.49(17)
C21 C20 H20 120.3
C19 C20 H20 120.3
C20 C21 C22 120.53(17)
C20 C21 H21 119.7
C22 C21 H21 119.7
C17 C22 C21 120.22(17)
C17 C22 H22 119.9
C21 C22 H22 119.9
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl1 C13 1.7383(17)
S1 C8 1.7384(15)
S1 C1 1.7409(16)
O1 C7 1.2256(19)
N1 C7 1.375(2)
N1 C6 1.4189(19)
N1 C16 1.4765(19)
C1 C2 1.398(2)
C1 C6 1.399(2)
C2 C3 1.381(3)
C2 H2 0.9500
C3 C4 1.385(3)
C3 H3 0.9500
C4 C5 1.388(3)
C4 H4 0.9500
C5 C6 1.398(2)
C5 H5 0.9500
C7 C8 1.500(2)
C8 C9 1.353(2)
C9 C10 1.459(2)
C9 H9 0.9500
C10 C11 1.404(2)
C10 C15 1.409(2)
C11 C12 1.394(2)
C11 H11 0.9500
C12 C13 1.383(2)
C12 H12 0.9500
C13 C14 1.388(2)
C14 C15 1.382(2)
C14 H14 0.9500
C15 H15 0.9500
C16 C17 1.511(2)
C16 H16A 0.9900
C16 H16B 0.9900
C17 C22 1.389(2)
C17 C18 1.390(2)
C18 C19 1.389(2)
C18 H18 0.9500
C19 C20 1.391(3)
C19 H19 0.9500
C20 C21 1.375(3)
C20 H20 0.9500
C21 C22 1.391(2)
C21 H21 0.9500
C22 H22 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
C16 H16B O1 3_676 0.99 2.43 3.271(2) 142
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 S1 C1 C2 -177.74(12)
C8 S1 C1 C6 3.15(15)
C6 C1 C2 C3 0.9(3)
S1 C1 C2 C3 -178.23(13)
C1 C2 C3 C4 -0.4(3)
C2 C3 C4 C5 -0.4(3)
C3 C4 C5 C6 0.8(3)
C4 C5 C6 C1 -0.3(2)
C4 C5 C6 N1 -179.15(15)
C2 C1 C6 C5 -0.6(2)
S1 C1 C6 C5 178.50(12)
C2 C1 C6 N1 178.28(14)
S1 C1 C6 N1 -2.7(2)
C7 N1 C6 C5 173.47(15)
C16 N1 C6 C5 -9.2(2)
C7 N1 C6 C1 -5.4(2)
C16 N1 C6 C1 171.94(14)
C6 N1 C7 O1 -169.28(14)
C16 N1 C7 O1 13.4(2)
C6 N1 C7 C8 11.9(2)
C16 N1 C7 C8 -165.44(13)
O1 C7 C8 C9 -9.2(2)
N1 C7 C8 C9 169.63(14)
O1 C7 C8 S1 171.00(12)
N1 C7 C8 S1 -10.2(2)
C1 S1 C8 C9 -176.80(13)
C1 S1 C8 C7 2.99(14)
C7 C8 C9 C10 177.40(15)
S1 C8 C9 C10 -2.8(2)
C8 C9 C10 C11 -1.7(3)
C8 C9 C10 C15 -178.50(16)
C15 C10 C11 C12 -1.0(2)
C9 C10 C11 C12 -177.82(15)
C10 C11 C12 C13 0.7(3)
C11 C12 C13 C14 0.2(3)
C11 C12 C13 Cl1 179.37(13)
C12 C13 C14 C15 -0.8(3)
Cl1 C13 C14 C15 -179.96(13)
C13 C14 C15 C10 0.5(3)
C11 C10 C15 C14 0.4(2)
C9 C10 C15 C14 177.50(15)
C7 N1 C16 C17 -105.82(16)
C6 N1 C16 C17 76.60(17)
N1 C16 C17 C22 -157.04(15)
N1 C16 C17 C18 24.9(2)
C22 C17 C18 C19 0.6(2)
C16 C17 C18 C19 178.62(16)
C17 C18 C19 C20 0.1(3)
C18 C19 C20 C21 -1.0(3)
C19 C20 C21 C22 1.0(3)
C18 C17 C22 C21 -0.5(2)
C16 C17 C22 C21 -178.64(15)
C20 C21 C22 C17 -0.3(3)

_cod_database_fobs_code 1543318
