#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/89/2228962.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_2228962
loop_
_publ_author_name
'Sridevi, D.'
'Bhaskaran, Sundari'
'Usha, G.'
'Murugan, G.'
'Bakthadoss, M.'
_publ_section_title
;
 3-(2-Methylbenzylidene)-2,3-dihydro-1,5-benzothiazepin-4(5H)-one
;
_journal_coeditor_code           BT5422
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o243
_journal_paper_doi               10.1107/S1600536810052888
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C17 H15 N O S'
_chemical_formula_moiety         'C17 H15 N O S'
_chemical_formula_sum            'C17 H15 N O S'
_chemical_formula_weight         281.36
_chemical_name_systematic
;
3-(2-Methylbenzylidene)-2,3-dihydro-1,5-benzothiazepin-4(5H)-one
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 128.5910(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   19.1192(5)
_cell_length_b                   13.0049(3)
_cell_length_c                   14.8903(4)
_cell_measurement_reflns_used    3560
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28
_cell_measurement_theta_min      2
_cell_volume                     2893.84(13)
_computing_cell_refinement       'SAINT (Bruker, 2004)'
_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_data_reduction        'SAINT and XPREP (Bruker, 2004)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material
'SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type  'Bruker Kappa APEXII CCD'
_diffrn_measurement_method       'ω and φ'
_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  0.0236
_diffrn_reflns_av_sigmaI/netI    0.0210
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            13879
_diffrn_reflns_theta_full        28.37
_diffrn_reflns_theta_max         28.37
_diffrn_reflns_theta_min         2.08
_exptl_absorpt_coefficient_mu    0.218
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.292
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1184
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.265
_refine_diff_density_min         -0.299
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.830
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     181
_refine_ls_number_reflns         3560
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.830
_refine_ls_R_factor_all          0.0595
_refine_ls_R_factor_gt           0.0437
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.2000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1684
_refine_ls_wR_factor_ref         0.2024
_reflns_number_gt                2707
_reflns_number_total             3560
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bt5422.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2228962
_cod_database_fobs_code          2228962
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -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_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.07250(13) 0.88179(15) 0.21097(16) 0.0540(5) Uani d . 1 . .
H H1 0.1146 0.9233 0.2730 0.065 Uiso calc R 1 . .
C C2 -0.00643(15) 0.92462(17) 0.11794(18) 0.0623(5) Uani d . 1 . .
H H2 -0.0169 0.9947 0.1164 0.075 Uiso calc R 1 . .
C C3 -0.06956(12) 0.86298(15) 0.02748(16) 0.0557(5) Uani d . 1 . .
H H3 -0.1233 0.8912 -0.0351 0.067 Uiso calc R 1 . .
C C4 -0.05362(11) 0.75966(14) 0.02896(14) 0.0448(4) Uani d . 1 . .
H H4 -0.0970 0.7185 -0.0326 0.054 Uiso calc R 1 . .
C C5 0.02685(10) 0.71567(12) 0.12171(12) 0.0365(4) Uani d . 1 . .
C C6 0.08537(12) 0.52859(14) 0.17690(13) 0.0485(4) Uani d . 1 . .
C C7 0.14280(11) 0.52918(13) 0.30555(12) 0.0424(4) Uani d . 1 . .
C C8 0.15581(12) 0.62540(13) 0.36935(13) 0.0478(4) Uani d . 1 . .
H H8A 0.1988 0.6123 0.4512 0.057 Uiso calc R 1 . .
H H8B 0.0995 0.6441 0.3523 0.057 Uiso calc R 1 . .
C C9 0.09042(10) 0.77806(13) 0.21391(13) 0.0398(4) Uani d . 1 . .
C C10 0.18328(12) 0.44083(13) 0.35720(14) 0.0477(4) Uani d . 1 . .
H H10 0.1742 0.3876 0.3092 0.057 Uiso calc R 1 . .
C C11 0.24053(11) 0.41648(13) 0.48045(14) 0.0449(4) Uani d . 1 . .
C C12 0.21413(14) 0.43985(16) 0.54648(16) 0.0573(5) Uani d . 1 . .
H H12 0.1612 0.4759 0.5135 0.069 Uiso calc R 1 . .
C C13 0.26536(17) 0.4103(2) 0.66057(18) 0.0723(7) Uani d . 1 . .
H H13 0.2472 0.4269 0.7040 0.087 Uiso calc R 1 . .
C C14 0.34253(16) 0.35663(19) 0.70886(18) 0.0750(7) Uani d . 1 . .
H H14 0.3770 0.3360 0.7853 0.090 Uiso calc R 1 . .
C C15 0.36932(13) 0.33310(17) 0.64501(18) 0.0676(6) Uani d . 1 . .
H H15 0.4222 0.2966 0.6792 0.081 Uiso calc R 1 . .
C C16 0.31970(11) 0.36225(14) 0.52991(15) 0.0504(4) Uani d . 1 . .
C C17 0.35129(16) 0.33506(19) 0.4639(2) 0.0722(6) Uani d . 1 . .
H H17A 0.4068 0.2983 0.5126 0.108 Uiso calc R 1 . .
H H17B 0.3601 0.3967 0.4366 0.108 Uiso calc R 1 . .
H H17C 0.3074 0.2926 0.3997 0.108 Uiso calc R 1 . .
N N 0.03793(9) 0.61072(12) 0.10949(10) 0.0450(4) Uani d . 1 . .
H H0 0.0047 0.5939 0.0381 0.054 Uiso calc R 1 . .
O O 0.07844(12) 0.44836(11) 0.12814(11) 0.0766(5) Uani d . 1 . .
S S1 0.19459(3) 0.73150(4) 0.33323(3) 0.0503(2) Uani 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 0.0033 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
C2 C1 C9 . . 121.29(17) ?
C2 C1 H1 . . 119.4 ?
C9 C1 H1 . . 119.4 ?
C3 C2 C1 . . 119.44(19) ?
C3 C2 H2 . . 120.3 ?
C1 C2 H2 . . 120.3 ?
C2 C3 C4 . . 120.29(17) ?
C2 C3 H3 . . 119.9 ?
C4 C3 H3 . . 119.9 ?
C3 C4 C5 . . 120.83(16) ?
C3 C4 H4 . . 119.6 ?
C5 C4 H4 . . 119.6 ?
C9 C5 C4 . . 118.81(15) ?
C9 C5 N . . 125.61(14) ?
C4 C5 N . . 115.48(14) ?
O C6 N . . 117.10(14) ?
O C6 C7 . . 118.78(15) ?
N C6 C7 . . 124.09(14) ?
C10 C7 C8 . . 123.34(14) ?
C10 C7 C6 . . 115.63(14) ?
C8 C7 C6 . . 120.97(14) ?
C7 C8 S1 . . 112.83(12) ?
C7 C8 H8A . . 109.0 ?
S1 C8 H8A . . 109.0 ?
C7 C8 H8B . . 109.0 ?
S1 C8 H8B . . 109.0 ?
H8A C8 H8B . . 107.8 ?
C1 C9 C5 . . 119.31(15) ?
C1 C9 S1 . . 118.05(13) ?
C5 C9 S1 . . 122.61(13) ?
C7 C10 C11 . . 128.30(16) ?
C7 C10 H10 . . 115.8 ?
C11 C10 H10 . . 115.8 ?
C16 C11 C12 . . 119.40(16) ?
C16 C11 C10 . . 119.11(17) ?
C12 C11 C10 . . 121.33(17) ?
C13 C12 C11 . . 121.1(2) ?
C13 C12 H12 . . 119.5 ?
C11 C12 H12 . . 119.5 ?
C14 C13 C12 . . 119.6(2) ?
C14 C13 H13 . . 120.2 ?
C12 C13 H13 . . 120.2 ?
C15 C14 C13 . . 119.99(19) ?
C15 C14 H14 . . 120.0 ?
C13 C14 H14 . . 120.0 ?
C14 C15 C16 . . 122.0(2) ?
C14 C15 H15 . . 119.0 ?
C16 C15 H15 . . 119.0 ?
C11 C16 C15 . . 117.93(19) ?
C11 C16 C17 . . 121.88(18) ?
C15 C16 C17 . . 120.2(2) ?
C16 C17 H17A . . 109.5 ?
C16 C17 H17B . . 109.5 ?
H17A C17 H17B . . 109.5 ?
C16 C17 H17C . . 109.5 ?
H17A C17 H17C . . 109.5 ?
H17B C17 H17C . . 109.5 ?
C6 N C5 . . 138.81(13) ?
C6 N H0 . . 110.6 ?
C5 N H0 . . 110.6 ?
C9 S1 C8 . . 98.53(8) ?
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
C1 C2 . 1.378(3) ?
C1 C9 . 1.386(2) ?
C1 H1 . 0.9300 ?
C2 C3 . 1.373(3) ?
C2 H2 . 0.9300 ?
C3 C4 . 1.375(3) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.397(2) ?
C4 H4 . 0.9300 ?
C5 C9 . 1.392(2) ?
C5 N . 1.410(2) ?
C6 O . 1.230(2) ?
C6 N . 1.355(2) ?
C6 C7 . 1.501(2) ?
C7 C10 . 1.330(2) ?
C7 C8 . 1.495(2) ?
C8 S1 . 1.8001(19) ?
C8 H8A . 0.9700 ?
C8 H8B . 0.9700 ?
C9 S1 . 1.7538(16) ?
C10 C11 . 1.470(2) ?
C10 H10 . 0.9300 ?
C11 C16 . 1.393(3) ?
C11 C12 . 1.390(3) ?
C12 C13 . 1.385(3) ?
C12 H12 . 0.9300 ?
C13 C14 . 1.363(3) ?
C13 H13 . 0.9300 ?
C14 C15 . 1.367(4) ?
C14 H14 . 0.9300 ?
C15 C16 . 1.397(3) ?
C15 H15 . 0.9300 ?
C16 C17 . 1.482(3) ?
C17 H17A . 0.9600 ?
C17 H17B . 0.9600 ?
C17 H17C . 0.9600 ?
N H0 . 0.8600 ?
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
N H0 O 5_565 0.86 2.01 2.8705(18) 177 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
C9 C1 C2 C3 . . . . 1.6(3) ?
C1 C2 C3 C4 . . . . -0.9(3) ?
C2 C3 C4 C5 . . . . -0.3(3) ?
C3 C4 C5 C9 . . . . 1.0(2) ?
C3 C4 C5 N . . . . -175.59(16) ?
O C6 C7 C10 . . . . 0.9(3) ?
N C6 C7 C10 . . . . 178.94(17) ?
O C6 C7 C8 . . . . 178.10(19) ?
N C6 C7 C8 . . . . -3.8(3) ?
C10 C7 C8 S1 . . . . 123.26(16) ?
C6 C7 C8 S1 . . . . -53.7(2) ?
C2 C1 C9 C5 . . . . -0.9(3) ?
C2 C1 C9 S1 . . . . 177.38(15) ?
C4 C5 C9 C1 . . . . -0.4(2) ?
N C5 C9 C1 . . . . 175.84(16) ?
C4 C5 C9 S1 . . . . -178.59(12) ?
N C5 C9 S1 . . . . -2.4(2) ?
C8 C7 C10 C11 . . . . 5.3(3) ?
C6 C7 C10 C11 . . . . -177.56(18) ?
C7 C10 C11 C16 . . . . -135.7(2) ?
C7 C10 C11 C12 . . . . 49.1(3) ?
C16 C11 C12 C13 . . . . 0.1(3) ?
C10 C11 C12 C13 . . . . 175.39(19) ?
C11 C12 C13 C14 . . . . -0.6(3) ?
C12 C13 C14 C15 . . . . 0.5(4) ?
C13 C14 C15 C16 . . . . -0.1(3) ?
C12 C11 C16 C15 . . . . 0.3(3) ?
C10 C11 C16 C15 . . . . -175.08(17) ?
C12 C11 C16 C17 . . . . 179.97(18) ?
C10 C11 C16 C17 . . . . 4.6(3) ?
C14 C15 C16 C11 . . . . -0.3(3) ?
C14 C15 C16 C17 . . . . -180.0(2) ?
O C6 N C5 . . . . -175.66(19) ?
C7 C6 N C5 . . . . 6.3(3) ?
C9 C5 N C6 . . . . 26.7(3) ?
C4 C5 N C6 . . . . -157.0(2) ?
C1 C9 S1 C8 . . . . 128.73(15) ?
C5 C9 S1 C8 . . . . -53.03(15) ?
C7 C8 S1 C9 . . . . 87.11(13) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30656450
