#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/10/2201095.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_2201095
loop_
_publ_author_name
'Laavanya, Parthasarathi'
'Panchanatheswaran, Krishnaswamy'
'Muthukumar, Manivannan'
'Jeyaraman, Ramasubbu'
'Krause Bauer, Jeanette A.'
_publ_section_title
;
 2,3,4,5-Tetrahydro-r-2,c-4-diphenyl-1,5-benzothiazepine
;
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o701
_journal_page_last               o702
_journal_paper_doi               10.1107/S160053680200853X
_journal_volume                  58
_journal_year                    2002
_chemical_formula_iupac          'C21 H19 N S'
_chemical_formula_moiety         'C21 H19 N S'
_chemical_formula_sum            'C21 H19 N S'
_chemical_formula_weight         317.43
_chemical_name_systematic
;
2,3,4,5-tetrahydro-r-2,c-4-diphenyl-1,5-benzothiazepine
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_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-97
_cell_angle_alpha                90.00
_cell_angle_beta                 107.327(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.4782(15)
_cell_length_b                   6.0737(7)
_cell_length_c                   21.918(3)
_cell_measurement_reflns_used    1726
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      28
_cell_measurement_theta_min      10
_cell_volume                     1712.8(4)
_computing_cell_refinement       'SAINT (Bruker, 1997)'
_computing_data_collection       'SMART (Bruker, 1997)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'ZORTEP (Zsolnai, 1997)'
_computing_publication_material
'SHELXL97 (Sheldrick, 1997) and PARST96 (Nardelli, 1983)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR97 (Altomare et al., 1997)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type  'Siemens SMART 1K CCD'
_diffrn_measurement_method       ω-2θ
_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  0.087
_diffrn_reflns_av_sigmaI/netI    0.1227
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            10671
_diffrn_reflns_theta_full        28.29
_diffrn_reflns_theta_max         28.29
_diffrn_reflns_theta_min         2.88
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.188
_exptl_absorpt_correction_T_max  0.985
_exptl_absorpt_correction_T_min  0.922
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.231
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.19
_refine_diff_density_min         -0.28
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.86
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     230
_refine_ls_number_reflns         4168
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.86
_refine_ls_R_factor_all          0.149
_refine_ls_R_factor_gt           0.054
_refine_ls_shift/su_max          <0.001
_refine_ls_shift/su_mean         <0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0529P)²] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.103
_refine_ls_wR_factor_ref         0.131
_reflns_number_gt                1824
_reflns_number_total             4168
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ci6126.cif
_cod_data_source_block           I
_cod_original_cell_volume        1712.9(3)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2201095
_cod_database_fobs_code          2201095
loop_
_symmetry_equiv_pos_as_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_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
_atom_site_type_symbol
S1 0.48346(5) 0.01363(11) 0.21604(3) 0.0472(2) Uani d . 1 . . S
C2 0.54426(17) 0.1918(4) 0.16927(12) 0.0376(6) Uani d . 1 . . C
H2 0.5703(7) 0.329(4) 0.1953(7) 0.0536(19) Uiso calc R 1 . . H
C3 0.46731(17) 0.2622(4) 0.10604(12) 0.0413(7) Uani d . 1 . . C
H3A 0.4541(3) 0.137(2) 0.0758(5) 0.0536(19) Uiso calc R 1 . . H
H3B 0.4980(5) 0.383(2) 0.0873(3) 0.0536(19) Uiso calc R 1 . . H
C4 0.36355(17) 0.3399(4) 0.11473(11) 0.0382(6) Uani d . 1 . . C
H4 0.3261(9) 0.207(3) 0.1238(3) 0.0536(19) Uiso calc R 1 . . H
N5 0.38407(17) 0.4882(4) 0.17049(10) 0.0415(6) Uani d . 1 . . N
H5 0.3539(17) 0.607(4) 0.1624(11) 0.031(7) Uiso d . 1 . . H
C6 0.34809(19) 0.5523(5) 0.26950(13) 0.0485(7) Uani d . 1 . . C
H6 0.3223(7) 0.698(4) 0.2536(5) 0.0536(19) Uiso calc R 1 . . H
C7 0.3479(2) 0.4895(6) 0.32974(15) 0.0596(9) Uani d . 1 . . C
H7 0.3232(7) 0.590(3) 0.3557(7) 0.0536(19) Uiso calc R 1 . . H
C8 0.3825(2) 0.2842(6) 0.35319(15) 0.0615(9) Uani d . 1 . . C
H8 0.3800(2) 0.2415(14) 0.3921(12) 0.0536(19) Uiso calc R 1 . . H
C9 0.42121(19) 0.1450(5) 0.31596(13) 0.0512(8) Uani d . 1 . . C
H9 0.4458(7) 0.003(4) 0.3320(4) 0.0536(19) Uiso calc R 1 . . H
C10 0.42529(17) 0.2063(4) 0.25539(12) 0.0380(6) Uani d . 1 . . C
C11 0.38459(17) 0.4111(4) 0.23052(12) 0.0379(6) Uani d . 1 . . C
C20 0.63783(18) 0.0677(4) 0.16231(12) 0.0413(7) Uani d . 1 . . C
C21 0.73709(18) 0.1488(5) 0.18881(12) 0.0434(7) Uani d . 1 . . C
H21 0.7467(3) 0.284(4) 0.2107(6) 0.0536(19) Uiso calc R 1 . . H
C22 0.8226(2) 0.0324(5) 0.18339(13) 0.0516(8) Uani d . 1 . . C
H22 0.8903(19) 0.0890(17) 0.2018(5) 0.0536(19) Uiso calc R 1 . . H
C23 0.8092(2) -0.1641(6) 0.15139(14) 0.0589(9) Uani d . 1 . . C
H23 0.8658(16) -0.239(2) 0.14774(18) 0.0536(19) Uiso calc R 1 . . H
C24 0.7115(2) -0.2488(6) 0.12479(15) 0.0622(9) Uani d . 1 . . C
H24 0.7026(4) -0.383(4) 0.1035(6) 0.0536(19) Uiso calc R 1 . . H
C25 0.6260(2) -0.1312(5) 0.13005(14) 0.0575(8) Uani d . 1 . . C
H25 0.5550(18) -0.1910(16) 0.1103(5) 0.0536(19) Uiso calc R 1 . . H
C30 0.29268(19) 0.4552(4) 0.05716(12) 0.0404(7) Uani d . 1 . . C
C31 0.1950(2) 0.3696(6) 0.02670(13) 0.0555(8) Uani d . 1 . . C
H31 0.1744(6) 0.230(4) 0.0406(4) 0.0536(19) Uiso calc R 1 . . H
C32 0.1268(3) 0.4819(7) -0.02313(14) 0.0711(10) Uani d . 1 . . C
H32 0.0644(18) 0.4260(18) -0.0422(6) 0.0536(19) Uiso calc R 1 . . H
C33 0.1546(3) 0.6768(7) -0.04321(16) 0.0742(11) Uani d . 1 . . C
H33 0.1104(14) 0.749(2) -0.0746(10) 0.0536(19) Uiso calc R 1 . . H
C34 0.2509(3) 0.7616(6) -0.01491(16) 0.0758(11) Uani d . 1 . . C
H34 0.2703(7) 0.891(4) -0.0290(4) 0.0536(19) Uiso calc R 1 . . H
C35 0.3183(2) 0.6508(5) 0.03482(14) 0.0608(9) Uani d . 1 . . C
H35 0.3881(18) 0.7146(17) 0.0553(6) 0.0536(19) Uiso calc R 1 . . H
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'
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
_geom_angle_publ_flag
C10 S1 C2 102.58(12) y
C20 C2 C3 114.2(2) y
C20 C2 S1 106.58(16) y
C3 C2 S1 112.07(17) y
C20 C2 H2 107.9 ?
C3 C2 H2 107.9 ?
S1 C2 H2 107.9 ?
C2 C3 C4 111.7(2) y
C2 C3 H3A 109.3 ?
C4 C3 H3A 109.3 ?
C2 C3 H3B 109.3 ?
C4 C3 H3B 109.3 ?
H3A C3 H3B 107.9 ?
N5 C4 C30 109.0(2) y
N5 C4 C3 109.64(19) y
C30 C4 C3 114.2(2) y
N5 C4 H4 107.9 ?
C30 C4 H4 107.9 ?
C3 C4 H4 107.9 ?
C11 N5 C4 121.5(2) y
C11 N5 H5 111.2(16) ?
C4 N5 H5 113.5(16) ?
C7 C6 C11 121.2(3) ?
C7 C6 H6 119.4 ?
C11 C6 H6 119.4 ?
C6 C7 C8 120.8(3) ?
C6 C7 H7 119.6 ?
C8 C7 H7 119.6 ?
C7 C8 C9 118.7(3) ?
C7 C8 H8 120.7 ?
C9 C8 H8 120.7 ?
C8 C9 C10 121.9(3) ?
C8 C9 H9 119.1 ?
C10 C9 H9 119.1 ?
C9 C10 C11 119.0(2) y
C9 C10 S1 115.8(2) y
C11 C10 S1 125.2(2) y
N5 C11 C6 117.8(2) y
N5 C11 C10 123.8(2) y
C6 C11 C10 118.3(2) y
C21 C20 C25 118.4(2) ?
C21 C20 C2 120.8(2) ?
C25 C20 C2 120.9(2) ?
C20 C21 C22 120.5(3) ?
C20 C21 H21 119.7 ?
C22 C21 H21 119.7 ?
C23 C22 C21 120.1(3) ?
C23 C22 H22 119.9 ?
C21 C22 H22 119.9 ?
C22 C23 C24 120.5(3) ?
C22 C23 H23 119.7 ?
C24 C23 H23 119.7 ?
C23 C24 C25 119.1(3) ?
C23 C24 H24 120.4 ?
C25 C24 H24 120.4 ?
C20 C25 C24 121.3(3) ?
C20 C25 H25 119.4 ?
C24 C25 H25 119.4 ?
C35 C30 C31 117.2(3) ?
C35 C30 C4 122.5(2) ?
C31 C30 C4 120.1(2) ?
C32 C31 C30 120.5(3) ?
C32 C31 H31 119.7 ?
C30 C31 H31 119.7 ?
C33 C32 C31 120.4(3) ?
C33 C32 H32 119.8 ?
C31 C32 H32 119.8 ?
C32 C33 C34 120.0(3) ?
C32 C33 H33 120.0 ?
C34 C33 H33 120.0 ?
C33 C34 C35 119.5(3) ?
C33 C34 H34 120.2 ?
C35 C34 H34 120.2 ?
C30 C35 C34 122.2(3) ?
C30 C35 H35 118.9 ?
C34 C35 H35 118.9 ?
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
S1 C10 . 1.770(3) y
S1 C2 . 1.842(2) y
C2 C20 . 1.515(3) y
C2 C3 . 1.524(3) y
C2 H2 . 1.01 ?
C3 C4 . 1.541(3) y
C3 H3A . 0.99 ?
C3 H3B . 0.99 ?
C4 N5 . 1.476(3) y
C4 C30 . 1.509(3) y
C4 H4 . 1.00 ?
N5 C11 . 1.395(3) y
N5 H5 . 0.82(2) ?
C6 C7 . 1.375(4) ?
C6 C11 . 1.399(3) ?
C6 H6 . 0.98 ?
C7 C8 . 1.376(4) ?
C7 H7 . 0.96 ?
C8 C9 . 1.380(4) ?
C8 H8 . 0.90 ?
C9 C10 . 1.396(3) ?
C9 H9 . 0.95 ?
C10 C11 . 1.402(3) y
C20 C21 . 1.381(3) ?
C20 C25 . 1.385(4) ?
C21 C22 . 1.387(3) ?
C21 H21 . 0.94 ?
C22 C23 . 1.369(4) ?
C22 H22 . 0.95 ?
C23 C24 . 1.372(4) ?
C23 H23 . 0.91 ?
C24 C25 . 1.389(4) ?
C24 H24 . 0.93 ?
C25 H25 . 0.99 ?
C30 C35 . 1.368(4) ?
C30 C31 . 1.388(3) ?
C31 C32 . 1.380(4) ?
C31 H31 . 0.97 ?
C32 C33 . 1.354(4) ?
C32 H32 . 0.89 ?
C33 C34 . 1.362(4) ?
C33 H33 . 0.88 ?
C34 C35 . 1.370(4) ?
C34 H34 . 0.91 ?
C35 H35 . 0.99 ?
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
_geom_torsion_publ_flag
C10 S1 C2 C20 151.07(17) y
C10 S1 C2 C3 -83.4(2) y
C20 C2 C3 C4 167.2(2) y
S1 C2 C3 C4 45.9(3) y
C2 C3 C4 N5 45.3(3) y
C2 C3 C4 C30 168.0(2) y
C30 C4 N5 C11 138.0(2) y
C3 C4 N5 C11 -96.3(3) y
C11 C6 C7 C8 -0.7(4) ?
C6 C7 C8 C9 2.3(4) ?
C7 C8 C9 C10 -0.5(4) ?
C8 C9 C10 C11 -3.0(4) ?
C8 C9 C10 S1 176.8(2) ?
C2 S1 C10 C9 -147.55(19) ?
C2 S1 C10 C11 32.2(2) y
C4 N5 C11 C6 -145.6(2) ?
C4 N5 C11 C10 38.4(3) y
C7 C6 C11 N5 -178.9(2) ?
C7 C6 C11 C10 -2.7(4) ?
C9 C10 C11 N5 -179.6(2) ?
S1 C10 C11 N5 0.7(3) y
C9 C10 C11 C6 4.4(3) ?
S1 C10 C11 C6 -175.28(18) ?
C3 C2 C20 C21 119.4(3) ?
S1 C2 C20 C21 -116.3(2) ?
C3 C2 C20 C25 -61.6(3) ?
S1 C2 C20 C25 62.7(3) ?
C25 C20 C21 C22 -0.3(4) ?
C2 C20 C21 C22 178.7(2) ?
C20 C21 C22 C23 0.2(4) ?
C21 C22 C23 C24 -0.4(4) ?
C22 C23 C24 C25 0.7(4) ?
C21 C20 C25 C24 0.7(4) ?
C2 C20 C25 C24 -178.4(3) ?
C23 C24 C25 C20 -0.9(5) ?
N5 C4 C30 C35 58.8(3) ?
C3 C4 C30 C35 -64.2(3) ?
N5 C4 C30 C31 -117.7(3) ?
C3 C4 C30 C31 119.3(3) ?
C35 C30 C31 C32 -1.3(4) ?
C4 C30 C31 C32 175.4(2) ?
C30 C31 C32 C33 0.3(4) ?
C31 C32 C33 C34 1.1(5) ?
C32 C33 C34 C35 -1.5(5) ?
C31 C30 C35 C34 0.9(4) ?
C4 C30 C35 C34 -175.7(3) ?
C33 C34 C35 C30 0.5(5) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 531421
