#------------------------------------------------------------------------------
#$Date: 2017-10-13 12:31:46 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/57/2235746.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_2235746
loop_
_publ_author_name
'Sabari, V.'
'Selvakumar, R.'
'Bakthadoss, M.'
'Aravindhan, S.'
_publ_section_title
;
 (Z)-3-Benzyl-1,5-benzothiazepin-4(5H)-one
;
_journal_coeditor_code           BT5942
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2329
_journal_paper_doi               10.1107/S1600536812029054
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          'C16 H13 N O S'
_chemical_formula_moiety         'C16 H13 N O S'
_chemical_formula_sum            'C16 H13 N O S'
_chemical_formula_weight         267.33
_chemical_name_systematic
;
(Z)-3-Benzyl-1,5-benzothiazepin-4(5H)-one
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_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-97
_cell_angle_alpha                90.00
_cell_angle_beta                 94.727(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.3409(6)
_cell_length_b                   11.7876(7)
_cell_length_c                   11.8310(6)
_cell_measurement_reflns_used    8725
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.0897
_cell_measurement_theta_min      2.7582
_cell_volume                     1298.24(13)
_computing_cell_refinement       'SAINT (Bruker, 2008)'
_computing_data_collection       'APEX2 (Bruker, 2008)'
_computing_data_reduction        'SAINT (Bruker, 2008)'
_computing_molecular_graphics    'ORTEP-3 (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_detector_area_resol_mean 15.9948
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker SMART APEXII CCD'
_diffrn_measurement_method       'ω and φ 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  0.0239
_diffrn_reflns_av_sigmaI/netI    0.0197
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            11696
_diffrn_reflns_theta_full        28.28
_diffrn_reflns_theta_max         28.28
_diffrn_reflns_theta_min         2.19
_exptl_absorpt_coefficient_mu    0.239
_exptl_absorpt_correction_T_max  0.9902
_exptl_absorpt_correction_T_min  0.9797
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2008)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.368
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       monoclinic
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.246
_refine_diff_density_min         -0.310
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     224
_refine_ls_number_reflns         3220
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0444
_refine_ls_R_factor_gt           0.0363
_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)+(0.0473P)²+0.3853P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0938
_refine_ls_wR_factor_ref         0.1001
_reflns_number_gt                2700
_reflns_number_total             3220
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bt5942.cif
_cod_data_source_block           I
_cod_original_sg_symbol_Hall     ' -P 2ybc'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2235746
_cod_database_fobs_code          2235746
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
H H10A 0.9319(19) 0.4199(16) 1.0576(15) 0.054(5) Uiso d 1 1
H H14 1.158(2) 0.0216(19) 1.2706(18) 0.071(6) Uiso d 1 1
H H13 1.253(3) 0.210(2) 1.287(2) 0.090(7) Uiso d 1 1
H H2 0.520(2) 0.0349(17) 0.7510(18) 0.067(6) Uiso d 1 1
H H4 0.264(2) 0.0652(19) 1.0082(18) 0.075(6) Uiso d 1 1
H H3 0.341(2) -0.0401(19) 0.8584(18) 0.078(6) Uiso d 1 1
H H5 0.367(2) 0.2445(15) 1.0477(16) 0.051(5) Uiso d 1 1
H H9 0.906(2) 0.2452(13) 0.8225(15) 0.047(4) Uiso d 1 1
H H12 1.152(2) 0.3537(18) 1.1720(16) 0.066(6) Uiso d 1 1
H H16 0.8605(18) 0.1324(14) 1.0263(14) 0.048(4) Uiso d 1 1
H H15 0.960(2) -0.0149(19) 1.1441(18) 0.075(6) Uiso d 1 1
H H 0.4802(19) 0.4003(15) 0.9656(14) 0.050(5) Uiso d 1 1
H H10B 1.0195(19) 0.3709(15) 0.9641(15) 0.053(5) Uiso d 1 1
S S1 0.67169(4) 0.23482(4) 0.74334(3) 0.04629(13) Uani d 1 1
O O1 0.69525(11) 0.49768(9) 1.00015(11) 0.0515(3) Uani d 1 1
N N1 0.54541(12) 0.35755(9) 0.94400(10) 0.0376(3) Uani d 1 1
C C9 0.81284(15) 0.27217(12) 0.84256(12) 0.0377(3) Uani d 1 1
C C1 0.54547(14) 0.18101(11) 0.83286(11) 0.0361(3) Uani d 1 1
C C8 0.80771(13) 0.33382(10) 0.93653(11) 0.0326(3) Uani d 1 1
C C7 0.67881(14) 0.40033(11) 0.96316(11) 0.0345(3) Uani d 1 1
C C10 0.94322(15) 0.35387(12) 1.01201(13) 0.0397(3) Uani d 1 1
C C6 0.49997(14) 0.24447(10) 0.92206(11) 0.0332(3) Uani d 1 1
C C11 0.99742(13) 0.25642(11) 1.08739(11) 0.0335(3) Uani d 1 1
C C16 0.94145(15) 0.14763(12) 1.08123(12) 0.0396(3) Uani d 1 1
C C12 1.11413(16) 0.27689(16) 1.16571(13) 0.0490(4) Uani d 1 1
C C5 0.39623(16) 0.20069(14) 0.98728(14) 0.0448(3) Uani d 1 1
C C14 1.11727(19) 0.08314(19) 1.22626(15) 0.0599(5) Uani d 1 1
C C13 1.17296(18) 0.1913(2) 1.23380(15) 0.0628(5) Uani d 1 1
C C2 0.48567(18) 0.07488(14) 0.80956(15) 0.0511(4) Uani d 1 1
C C15 1.00050(19) 0.06142(15) 1.15013(14) 0.0508(4) Uani d 1 1
C C4 0.33594(18) 0.09600(16) 0.96179(17) 0.0568(4) Uani d 1 1
C C3 0.37969(19) 0.03362(15) 0.87283(18) 0.0613(5) 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
C9 S1 C1 101.05(6)
C7 N1 C6 129.99(11)
C7 N1 H 114.0(12)
C6 N1 H 113.8(12)
C8 C9 S1 128.37(11)
C8 C9 H9 118.4(10)
S1 C9 H9 113.2(10)
C2 C1 C6 119.54(13)
C2 C1 S1 118.81(11)
C6 C1 S1 121.57(10)
C9 C8 C7 123.22(12)
C9 C8 C10 119.61(12)
C7 C8 C10 116.46(12)
O1 C7 N1 119.66(12)
O1 C7 C8 119.00(12)
N1 C7 C8 121.30(11)
C8 C10 C11 116.97(11)
C8 C10 H10A 109.6(11)
C11 C10 H10A 109.4(11)
C8 C10 H10B 107.9(10)
C11 C10 H10B 106.0(11)
H10A C10 H10B 106.3(15)
C5 C6 C1 119.61(13)
C5 C6 N1 117.44(12)
C1 C6 N1 122.71(12)
C16 C11 C12 117.84(14)
C16 C11 C10 124.38(12)
C12 C11 C10 117.75(13)
C11 C16 C15 121.13(14)
C11 C16 H16 118.4(10)
C15 C16 H16 120.4(10)
C13 C12 C11 121.01(17)
C13 C12 H12 120.7(12)
C11 C12 H12 118.2(12)
C4 C5 C6 120.17(15)
C4 C5 H5 121.1(11)
C6 C5 H5 118.7(11)
C13 C14 C15 119.21(16)
C13 C14 H14 122.2(13)
C15 C14 H14 118.5(13)
C14 C13 C12 120.67(16)
C14 C13 H13 121.2(15)
C12 C13 H13 118.1(15)
C3 C2 C1 120.36(15)
C3 C2 H2 122.7(13)
C1 C2 H2 117.0(13)
C14 C15 C16 120.12(17)
C14 C15 H15 120.0(12)
C16 C15 H15 119.9(13)
C3 C4 C5 120.30(16)
C3 C4 H4 119.7(13)
C5 C4 H4 120.0(13)
C4 C3 C2 119.98(16)
C4 C3 H3 119.7(13)
C2 C3 H3 120.2(13)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 C9 1.7479(15)
S1 C1 1.7663(14)
O1 C7 1.2332(16)
N1 C7 1.3460(17)
N1 C6 1.4165(16)
N1 H 0.846(18)
C9 C8 1.3324(19)
C9 H9 0.976(18)
C1 C2 1.388(2)
C1 C6 1.3885(18)
C8 C7 1.4920(17)
C8 C10 1.5064(19)
C10 C11 1.515(2)
C10 H10A 0.958(19)
C10 H10B 0.968(18)
C6 C5 1.387(2)
C11 C16 1.3845(19)
C11 C12 1.392(2)
C16 C15 1.388(2)
C16 H16 0.972(17)
C12 C13 1.377(3)
C12 H12 0.97(2)
C5 C4 1.379(2)
C5 H5 0.942(19)
C14 C13 1.377(3)
C14 C15 1.380(3)
C14 H14 0.96(2)
C13 H13 0.96(3)
C2 C3 1.378(3)
C2 H2 0.92(2)
C15 H15 0.98(2)
C4 C3 1.373(3)
C4 H4 0.97(2)
C3 H3 0.95(2)
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
N1 H O1 3_667 0.847(18) 2.098(19) 2.9407(15) 173.1(16)
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
C1 S1 C9 C8 -49.95(14)
C9 S1 C1 C2 -128.63(12)
C9 S1 C1 C6 54.52(12)
S1 C9 C8 C7 -11.3(2)
S1 C9 C8 C10 178.70(10)
C6 N1 C7 O1 -167.26(14)
C6 N1 C7 C8 15.0(2)
C9 C8 C7 O1 -135.97(15)
C10 C8 C7 O1 34.35(18)
C9 C8 C7 N1 41.8(2)
C10 C8 C7 N1 -147.91(13)
C9 C8 C10 C11 -76.59(17)
C7 C8 C10 C11 112.72(14)
C2 C1 C6 C5 0.5(2)
S1 C1 C6 C5 177.32(11)
C2 C1 C6 N1 -173.63(13)
S1 C1 C6 N1 3.20(18)
C7 N1 C6 C5 129.13(16)
C7 N1 C6 C1 -56.6(2)
C8 C10 C11 C16 8.3(2)
C8 C10 C11 C12 -173.77(12)
C12 C11 C16 C15 -0.6(2)
C10 C11 C16 C15 177.38(14)
C16 C11 C12 C13 0.8(2)
C10 C11 C12 C13 -177.31(14)
C1 C6 C5 C4 -1.7(2)
N1 C6 C5 C4 172.74(14)
C15 C14 C13 C12 -0.6(3)
C11 C12 C13 C14 -0.2(3)
C6 C1 C2 C3 1.4(2)
S1 C1 C2 C3 -175.52(14)
C13 C14 C15 C16 0.8(3)
C11 C16 C15 C14 -0.2(2)
C6 C5 C4 C3 1.0(3)
C5 C4 C3 C2 0.9(3)
C1 C2 C3 C4 -2.1(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30657941
