#------------------------------------------------------------------------------
#$Date: 2016-02-21 01:03:34 +0100 (dom 21 de feb de 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/95/2239579.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_2239579
loop_
_publ_author_name
'Sebbar, Nada Kheira'
'El Fal, Mohammed'
'Essassi, El Mokhtar'
'Saadi, Mohamed'
'El Ammari, Lahcen'
_publ_section_title
;
 (2Z)-2-Benzylidene-4-n-butyl-3,4-dihydro-2H-1,4-benzothiazin-3-one
;
_journal_coeditor_code           TK5313
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o686
_journal_paper_doi               10.1107/S160053681401054X
_journal_volume                  70
_journal_year                    2014
_chemical_formula_iupac          'C19 H19 N O S'
_chemical_formula_moiety         'C19 H19 N O S'
_chemical_formula_sum            'C19 H19 N O S'
_chemical_formula_weight         309.41
_chemical_melting_point          363
_chemical_name_systematic
(2Z)-2-Benzylidene-4-n-utyl-3,4-dihydro-2H-1,4-benzothiazin-3-one
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_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-97
_cell_angle_alpha                88.283(9)
_cell_angle_beta                 82.302(9)
_cell_angle_gamma                60.895(8)
_cell_formula_units_Z            2
_cell_length_a                   8.7717(13)
_cell_length_b                   8.8631(13)
_cell_length_c                   12.3184(16)
_cell_measurement_reflns_used    3923
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.87
_cell_measurement_theta_min      2.63
_cell_volume                     828.5(2)
_computing_cell_refinement       'SAINT (Bruker, 2009)'
_computing_data_collection       'APEX2 (Bruker, 2009)'
_computing_data_reduction        'SAINT (Bruker, 2009)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 2012)'
_computing_publication_material
'PLATON (Spek, 2009) and publCIF (Westrip, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker X8 APEX'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0328
_diffrn_reflns_av_sigmaI/netI    0.0282
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            17374
_diffrn_reflns_theta_full        27.87
_diffrn_reflns_theta_max         27.87
_diffrn_reflns_theta_min         2.63
_exptl_absorpt_coefficient_mu    0.197
_exptl_absorpt_correction_T_max  0.7464
_exptl_absorpt_correction_T_min  0.6414
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2009)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.240
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             328
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.28
_refine_diff_density_max         0.281
_refine_diff_density_min         -0.225
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         3923
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0630
_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
'calc w=1/[σ²(Fo²)+(0.0610P)²+0.1635P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1152
_refine_ls_wR_factor_ref         0.1285
_reflns_number_gt                2912
_reflns_number_total             3923
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            tk5313sup1.cif
_cod_data_source_block           I
_cod_database_code               2239579
_cod_database_fobs_code          2239579
loop_
_symmetry_equiv_pos_as_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_refinement_flags
_atom_site_occupancy
_atom_site_symmetry_multiplicity
C C1 0.9210(2) 0.3479(2) 0.82655(15) 0.0483(4) Uani d . 1 1
C C2 1.0667(3) 0.2113(2) 0.76691(19) 0.0648(5) Uani d . 1 1
H H2 1.0839 0.2136 0.6909 0.078 Uiso calc R 1 1
C C3 1.1845(3) 0.0746(3) 0.8185(2) 0.0758(7) Uani d . 1 1
H H3 1.2794 -0.0181 0.7779 0.091 Uiso calc R 1 1
C C4 1.1622(3) 0.0746(3) 0.9299(2) 0.0761(7) Uani d . 1 1
H H4 1.2449 -0.0169 0.9653 0.091 Uiso calc R 1 1
C C5 1.0181(3) 0.2089(2) 0.99169(18) 0.0622(5) Uani d . 1 1
H H5 1.0048 0.2067 1.0678 0.075 Uiso calc R 1 1
C C6 0.8931(2) 0.3472(2) 0.93992(14) 0.0447(4) Uani d . 1 1
C C7 0.6448(2) 0.6452(2) 0.96790(12) 0.0416(3) Uani d . 1 1
C C8 0.69106(19) 0.6857(2) 0.85347(12) 0.0408(3) Uani d . 1 1
C C9 0.6528(2) 0.8484(2) 0.83178(12) 0.0449(4) Uani d . 1 1
H H9 0.5991 0.9273 0.8912 0.054 Uiso calc R 1 1
C C10 0.6840(2) 0.9191(2) 0.72724(13) 0.0466(4) Uani d . 1 1
C C11 0.6707(3) 0.8635(3) 0.62735(15) 0.0647(5) Uani d . 1 1
H H11 0.6374 0.7790 0.6247 0.078 Uiso calc R 1 1
C C12 0.7061(3) 0.9318(3) 0.53127(16) 0.0779(7) Uani d . 1 1
H H12 0.6960 0.8930 0.4646 0.093 Uiso calc R 1 1
C C13 0.7560(3) 1.0563(3) 0.53309(18) 0.0795(7) Uani d . 1 1
H H13 0.7860 1.0976 0.4680 0.095 Uiso calc R 1 1
C C14 0.7610(4) 1.1182(3) 0.6313(2) 0.0900(8) Uani d . 1 1
H H14 0.7893 1.2064 0.6335 0.108 Uiso calc R 1 1
C C15 0.7245(3) 1.0520(3) 0.72774(17) 0.0720(6) Uani d . 1 1
H H15 0.7271 1.0971 0.7942 0.086 Uiso calc R 1 1
C C16 0.6813(2) 0.4450(2) 1.11277(13) 0.0498(4) Uani d . 1 1
H H16A 0.7185 0.3226 1.1158 0.060 Uiso calc R 1 1
H H16B 0.5536 0.5075 1.1257 0.060 Uiso calc R 1 1
C C17 0.7506(3) 0.4944(3) 1.20408(14) 0.0575(5) Uani d . 1 1
H H17A 0.7010 0.6189 1.2084 0.069 Uiso calc R 1 1
H H17B 0.8776 0.4429 1.1879 0.069 Uiso calc R 1 1
C C18 0.7032(4) 0.4335(4) 1.31329(17) 0.0835(7) Uani d . 1 1
H H18A 0.5767 0.4786 1.3261 0.100 Uiso calc R 1 1
H H18B 0.7586 0.3084 1.3093 0.100 Uiso calc R 1 1
C C19 0.7580(5) 0.4878(5) 1.4086(2) 0.1144(11) Uani d . 1 1
H H19A 0.7221 0.4471 1.4750 0.172 Uiso calc R 1 1
H H19B 0.7032 0.6116 1.4136 0.172 Uiso calc R 1 1
H H19C 0.8837 0.4394 1.3983 0.172 Uiso calc R 1 1
N N1 0.73979(17) 0.48044(16) 1.00182(10) 0.0425(3) Uani d . 1 1
O O1 0.52331(16) 0.75693(15) 1.02912(9) 0.0587(3) Uani d . 1 1
S S1 0.77675(6) 0.51831(6) 0.75323(3) 0.05429(16) Uani d . 1 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 C1 C2 120.52(18)
C6 C1 S1 121.86(12)
C2 C1 S1 117.62(16)
C3 C2 C1 120.8(2)
C3 C2 H2 119.6
C1 C2 H2 119.6
C4 C3 C2 119.40(19)
C4 C3 H3 120.3
C2 C3 H3 120.3
C3 C4 C5 121.1(2)
C3 C4 H4 119.5
C5 C4 H4 119.5
C4 C5 C6 120.2(2)
C4 C5 H5 119.9
C6 C5 H5 119.9
C1 C6 C5 117.94(16)
C1 C6 N1 121.31(14)
C5 C6 N1 120.73(16)
O1 C7 N1 120.87(14)
O1 C7 C8 120.34(14)
N1 C7 C8 118.79(13)
C9 C8 C7 118.94(14)
C9 C8 S1 123.81(12)
C7 C8 S1 117.05(12)
C8 C9 C10 128.90(15)
C8 C9 H9 115.5
C10 C9 H9 115.5
C11 C10 C15 117.53(17)
C11 C10 C9 123.43(17)
C15 C10 C9 119.02(16)
C10 C11 C12 120.8(2)
C10 C11 H11 119.6
C12 C11 H11 119.6
C13 C12 C11 120.6(2)
C13 C12 H12 119.7
C11 C12 H12 119.7
C14 C13 C12 119.0(2)
C14 C13 H13 120.5
C12 C13 H13 120.5
C13 C14 C15 120.8(2)
C13 C14 H14 119.6
C15 C14 H14 119.6
C14 C15 C10 121.0(2)
C14 C15 H15 119.5
C10 C15 H15 119.5
N1 C16 C17 114.51(14)
N1 C16 H16A 108.6
C17 C16 H16A 108.6
N1 C16 H16B 108.6
C17 C16 H16B 108.6
H16A C16 H16B 107.6
C16 C17 C18 110.99(16)
C16 C17 H17A 109.4
C18 C17 H17A 109.4
C16 C17 H17B 109.4
C18 C17 H17B 109.4
H17A C17 H17B 108.0
C19 C18 C17 113.8(2)
C19 C18 H18A 108.8
C17 C18 H18A 108.8
C19 C18 H18B 108.8
C17 C18 H18B 108.8
H18A C18 H18B 107.7
C18 C19 H19A 109.5
C18 C19 H19B 109.5
H19A C19 H19B 109.5
C18 C19 H19C 109.5
H19A C19 H19C 109.5
H19B C19 H19C 109.5
C7 N1 C6 124.49(13)
C7 N1 C16 116.46(13)
C6 N1 C16 118.97(13)
C1 S1 C8 99.56(8)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C6 1.386(2)
C1 C2 1.391(2)
C1 S1 1.7505(19)
C2 C3 1.361(3)
C2 H2 0.9300
C3 C4 1.360(4)
C3 H3 0.9300
C4 C5 1.388(3)
C4 H4 0.9300
C5 C6 1.394(2)
C5 H5 0.9300
C6 N1 1.421(2)
C7 O1 1.2199(18)
C7 N1 1.369(2)
C7 C8 1.496(2)
C8 C9 1.339(2)
C8 S1 1.7514(16)
C9 C10 1.466(2)
C9 H9 0.9300
C10 C11 1.379(3)
C10 C15 1.386(3)
C11 C12 1.380(3)
C11 H11 0.9300
C12 C13 1.373(4)
C12 H12 0.9300
C13 C14 1.358(3)
C13 H13 0.9300
C14 C15 1.377(3)
C14 H14 0.9300
C15 H15 0.9300
C16 N1 1.474(2)
C16 C17 1.516(2)
C16 H16A 0.9700
C16 H16B 0.9700
C17 C18 1.516(3)
C17 H17A 0.9700
C17 H17B 0.9700
C18 C19 1.500(3)
C18 H18A 0.9700
C18 H18B 0.9700
C19 H19A 0.9600
C19 H19B 0.9600
C19 H19C 0.9600
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
C4 H4 O1 1_645 0.93 2.50 3.407(2) 165
