#------------------------------------------------------------------------------
#$Date: 2017-10-13 12:31:46 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/53/2235372.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_2235372
loop_
_publ_author_name
'Sabari, V.'
'Selvakumar, R.'
'Bakthadoss, M.'
'Aravindhan, S.'
_publ_section_title
;
 (Z)-3-(2-Chlorobenzyl)-1,5-benzothiazepin-4(5H)-one
;
_journal_coeditor_code           BT5944
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2283
_journal_paper_doi               10.1107/S1600536812029030
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          'C16 H12 Cl N O S'
_chemical_formula_moiety         'C16 H12 Cl N O S'
_chemical_formula_sum            'C16 H12 Cl N O S'
_chemical_formula_weight         301.78
_chemical_name_systematic
;
(Z)-3-(2-Chlorobenzyl)-1,5-benzothiazepin-4(5H)-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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                101.9300(10)
_cell_angle_beta                 95.179(2)
_cell_angle_gamma                90.314(2)
_cell_formula_units_Z            2
_cell_length_a                   8.4958(3)
_cell_length_b                   8.7197(3)
_cell_length_c                   10.0520(3)
_cell_measurement_reflns_used    8725
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      29.0897
_cell_measurement_theta_min      2.7582
_cell_volume                     725.38(4)
_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      298(2)
_diffrn_detector_area_resol_mean 15.9948
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.965
_diffrn_measurement_device_type  'Bruker APEXII CCD area-detector'
_diffrn_measurement_method       'φ and ω'
_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  0.0197
_diffrn_reflns_av_sigmaI/netI    0.0198
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            10314
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         28.59
_diffrn_reflns_theta_min         2.08
_exptl_absorpt_coefficient_mu    0.401
_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    1.382
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       triclinic
_exptl_crystal_F_000             312
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.512
_refine_diff_density_min         -0.535
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.929
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     185
_refine_ls_number_reflns         3596
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.929
_refine_ls_R_factor_all          0.0544
_refine_ls_R_factor_gt           0.0443
_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)+(0.0686P)²+0.3987P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1189
_refine_ls_wR_factor_ref         0.1286
_reflns_number_gt                2961
_reflns_number_total             3596
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bt5944.cif
_cod_data_source_block           I
_cod_original_sg_symbol_Hall     ' -P 1'
_cod_database_code               2235372
_cod_database_fobs_code          2235372
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 0.3986(3) 0.7811(3) 0.4385(2) 0.0611(6) Uani d . 1 1
H H1 0.3329 0.7850 0.3602 0.073 Uiso calc R 1 1
C C2 0.5362(3) 0.6996(3) 0.4275(3) 0.0727(7) Uani d . 1 1
H H2 0.5640 0.6500 0.3421 0.087 Uiso calc R 1 1
C C3 0.6327(3) 0.6915(3) 0.5429(3) 0.0686(6) Uani d . 1 1
H H3 0.7259 0.6362 0.5354 0.082 Uiso calc R 1 1
C C4 0.5921(2) 0.7650(3) 0.6696(2) 0.0554(5) Uani d . 1 1
H H4 0.6578 0.7587 0.7474 0.066 Uiso calc R 1 1
C C5 0.45365(19) 0.8482(2) 0.68197(17) 0.0400(4) Uani d . 1 1
N N1 0.42278(17) 0.92803(19) 0.81405(14) 0.0425(3) Uani d . 1 1
C C6 0.29024(18) 0.92977(19) 0.87848(16) 0.0352(3) Uani d . 1 1
C C7 0.13755(18) 0.85995(19) 0.80480(17) 0.0361(3) Uani d . 1 1
C C8 0.0826(2) 0.8806(2) 0.68177(19) 0.0455(4) Uani d . 1 1
H H8 -0.0194 0.8430 0.6497 0.055 Uiso calc R 1 1
C C9 0.3563(2) 0.8580(2) 0.56553(17) 0.0429(4) Uani d . 1 1
C C10 0.0416(2) 0.7741(2) 0.88754(19) 0.0435(4) Uani d . 1 1
H H10A 0.0236 0.8440 0.9730 0.052 Uiso calc R 1 1
H H10B -0.0604 0.7426 0.8376 0.052 Uiso calc R 1 1
C C11 0.12551(19) 0.6308(2) 0.91707(17) 0.0382(4) Uani d . 1 1
C C12 0.2153(2) 0.6381(2) 1.0410(2) 0.0506(4) Uani d . 1 1
H H12 0.2198 0.7312 1.1062 0.061 Uiso calc R 1 1
C C13 0.2978(3) 0.5119(3) 1.0702(2) 0.0615(6) Uani d . 1 1
H H13 0.3578 0.5212 1.1538 0.074 Uiso calc R 1 1
C C14 0.2922(3) 0.3731(3) 0.9772(3) 0.0622(6) Uani d . 1 1
H H14 0.3486 0.2882 0.9970 0.075 Uiso calc R 1 1
C C15 0.2030(3) 0.3594(3) 0.8545(2) 0.0594(5) Uani d . 1 1
H H15 0.1969 0.2646 0.7914 0.071 Uiso calc R 1 1
C C16 0.1220(2) 0.4874(2) 0.82485(18) 0.0466(4) Uani d . 1 1
Cl Cl1 0.01021(9) 0.46470(9) 0.66795(6) 0.0789(2) Uani d . 1 1
O O1 0.29428(15) 0.98862(16) 1.00167(12) 0.0457(3) Uani d . 1 1
S S1 0.18502(6) 0.97237(7) 0.57440(5) 0.05265(16) Uani d . 1 1
H H1A 0.501(3) 0.958(3) 0.867(2) 0.051(6) Uiso 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'
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
C2 C1 C9 120.8(2)
C2 C1 H1 119.6
C9 C1 H1 119.6
C3 C2 C1 119.9(2)
C3 C2 H2 120.0
C1 C2 H2 120.0
C2 C3 C4 120.2(2)
C2 C3 H3 119.9
C4 C3 H3 119.9
C3 C4 C5 120.4(2)
C3 C4 H4 119.8
C5 C4 H4 119.8
C4 C5 C9 119.62(17)
C4 C5 N1 117.68(16)
C9 C5 N1 122.60(17)
C6 N1 C5 129.94(14)
C6 N1 H1A 112.3(15)
C5 N1 H1A 115.5(16)
O1 C6 N1 119.72(14)
O1 C6 C7 118.76(15)
N1 C6 C7 121.52(14)
C8 C7 C6 123.87(16)
C8 C7 C10 121.87(15)
C6 C7 C10 114.06(14)
C7 C8 S1 125.94(14)
C7 C8 H8 117.0
S1 C8 H8 117.0
C5 C9 C1 119.06(19)
C5 C9 S1 121.50(14)
C1 C9 S1 119.38(15)
C11 C10 C7 111.24(14)
C11 C10 H10A 109.4
C7 C10 H10A 109.4
C11 C10 H10B 109.4
C7 C10 H10B 109.4
H10A C10 H10B 108.0
C12 C11 C16 116.03(17)
C12 C11 C10 120.21(16)
C16 C11 C10 123.74(16)
C13 C12 C11 122.1(2)
C13 C12 H12 118.9
C11 C12 H12 118.9
C14 C13 C12 120.3(2)
C14 C13 H13 119.8
C12 C13 H13 119.8
C13 C14 C15 119.7(2)
C13 C14 H14 120.2
C15 C14 H14 120.2
C14 C15 C16 119.7(2)
C14 C15 H15 120.1
C16 C15 H15 120.1
C15 C16 C11 122.12(18)
C15 C16 Cl1 118.14(16)
C11 C16 Cl1 119.73(15)
C8 S1 C9 99.34(8)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.372(4)
C1 C9 1.393(3)
C1 H1 0.9300
C2 C3 1.373(4)
C2 H2 0.9300
C3 C4 1.378(3)
C3 H3 0.9300
C4 C5 1.387(3)
C4 H4 0.9300
C5 C9 1.389(2)
C5 N1 1.414(2)
N1 C6 1.347(2)
N1 H1A 0.81(2)
C6 O1 1.236(2)
C6 C7 1.494(2)
C7 C8 1.330(2)
C7 C10 1.513(2)
C8 S1 1.7554(19)
C8 H8 0.9300
C9 S1 1.767(2)
C10 C11 1.510(3)
C10 H10A 0.9700
C10 H10B 0.9700
C11 C12 1.390(3)
C11 C16 1.393(3)
C12 C13 1.376(3)
C12 H12 0.9300
C13 C14 1.366(3)
C13 H13 0.9300
C14 C15 1.371(3)
C14 H14 0.9300
C15 C16 1.384(3)
C15 H15 0.9300
C16 Cl1 1.740(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 H1A O1 2_677 0.82(2) 2.08(2) 2.8911(19) 174(3)
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
C9 C1 C2 C3 0.9(4)
C1 C2 C3 C4 -0.1(4)
C2 C3 C4 C5 -0.2(4)
C3 C4 C5 C9 -0.4(3)
C3 C4 C5 N1 -176.6(2)
C4 C5 N1 C6 -131.9(2)
C9 C5 N1 C6 52.0(3)
C5 N1 C6 O1 169.22(17)
C5 N1 C6 C7 -9.9(3)
O1 C6 C7 C8 136.80(19)
N1 C6 C7 C8 -44.0(3)
O1 C6 C7 C10 -38.0(2)
N1 C6 C7 C10 141.13(17)
C6 C7 C8 S1 7.7(3)
C10 C7 C8 S1 -177.85(14)
C4 C5 C9 C1 1.2(3)
N1 C5 C9 C1 177.26(17)
C4 C5 C9 S1 -176.03(15)
N1 C5 C9 S1 0.0(2)
C2 C1 C9 C5 -1.5(3)
C2 C1 C9 S1 175.81(18)
C8 C7 C10 C11 119.48(19)
C6 C7 C10 C11 -65.55(19)
C7 C10 C11 C12 96.9(2)
C7 C10 C11 C16 -81.8(2)
C16 C11 C12 C13 0.9(3)
C10 C11 C12 C13 -177.81(19)
C11 C12 C13 C14 -0.7(3)
C12 C13 C14 C15 -0.4(4)
C13 C14 C15 C16 1.3(3)
C14 C15 C16 C11 -1.1(3)
C14 C15 C16 Cl1 -179.98(17)
C12 C11 C16 C15 0.0(3)
C10 C11 C16 C15 178.67(17)
C12 C11 C16 Cl1 178.87(14)
C10 C11 C16 Cl1 -2.4(2)
C7 C8 S1 C9 55.28(19)
C5 C9 S1 C8 -59.33(16)
C1 C9 S1 C8 123.43(16)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30657848
