#------------------------------------------------------------------------------
#$Date: 2016-02-20 00:18:51 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176760 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/73/2017385.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_2017385
loop_
_publ_author_name
'Kanagasabapathy, Thanikasalam'
'Krishnaswamy, Panchanatheswaran'
'Ramasubbu, Jeyaraman'
_publ_section_title
;rac-5-Diphenylacetyl-2,2,4-trimethyl-2,3,4,5-tetrahydro-1,5-benzothiazepine
 and
 rac-5-formyl-2,2,4-trimethyl-2,3,4,5-tetrahydro-1,5-benzothiazepine
;
_journal_coeditor_code           GD3302
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o579
_journal_page_last               o582
_journal_paper_doi               10.1107/S0108270109036646
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C13 H17 N O S'
_chemical_formula_moiety         'C13 H17 N O S'
_chemical_formula_sum            'C13 H17 N O S'
_chemical_formula_weight         235.34
_chemical_name_common
;
 rac-5-formyl-2,3,4,5-tetrahydro-2,2,4-trimethyl-1,5-benzothiazepine
;
_chemical_name_systematic
;
 rac-5-formyl-2,3,4,5-tetrahydro-2,2,4-trimethyl-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
_cell_angle_alpha                90.00
_cell_angle_beta                 107.713(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.6038(8)
_cell_length_b                   9.9485(8)
_cell_length_c                   13.6818(11)
_cell_measurement_reflns_used    4056
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      31.71
_cell_measurement_theta_min      2.30
_cell_volume                     1245.23(18)
_computing_cell_refinement
;
APEX2 (Bruker, 2004) and SAINT (Bruker, 2004)
;
_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_data_reduction
;
SAINT (Bruker, 2004) and XPREP (Bruker, 2004)
;
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.960
_diffrn_measurement_device_type  'Bruker Kappa APEXII CCD area-detector'
_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  0.0238
_diffrn_reflns_av_sigmaI/netI    0.0223
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            17043
_diffrn_reflns_theta_full        29.80
_diffrn_reflns_theta_max         31.71
_diffrn_reflns_theta_min         2.30
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.239
_exptl_absorpt_correction_T_max  0.9765
_exptl_absorpt_correction_T_min  0.9339
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 1999)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.255
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             504
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.357
_refine_diff_density_min         -0.378
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     165
_refine_ls_number_reflns         4056
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0637
_refine_ls_R_factor_gt           0.0414
_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)+(0.0565P)²+0.2159P] where  P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1101
_refine_ls_wR_factor_ref         0.1238
_reflns_number_gt                2895
_reflns_number_total             4056
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            gd3302.cif
_cod_data_source_block           II
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2017385
_cod_database_fobs_code          2017385
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_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
S S1 0.46889(4) 0.78816(4) 0.21250(3) 0.05617(13) Uani d . 1 . .
C C2 0.37838(14) 0.95471(13) 0.19824(10) 0.0423(3) Uani d . 1 . .
C C3 0.32279(13) 1.00081(13) 0.08716(9) 0.0397(3) Uani d . 1 . .
H H3A 0.4057 0.9965 0.0585 0.040(4) Uiso calc R 1 . .
H H3B 0.2946 1.0965 0.0871 0.051(4) Uiso calc R 1 . .
C C4 0.19478(12) 0.92612(12) 0.01388(9) 0.0388(3) Uani d . 1 . .
H H4 0.1080 0.9384 0.0388 0.044(4) Uiso calc R 1 . .
N N5 0.22255(10) 0.78067(10) 0.01104(8) 0.0377(2) Uani d . 1 . .
C C6 0.36082(12) 0.73613(12) 0.00468(10) 0.0373(3) Uani d . 1 . .
C C7 0.48317(13) 0.74458(13) 0.09141(11) 0.0413(3) Uani d . 1 . .
C C8 0.61828(14) 0.70331(14) 0.08300(14) 0.0542(4) Uani d . 1 . .
H H8 0.7033 0.7107 0.1407 0.069(5) Uiso calc R 1 . .
C C9 0.62994(16) 0.65211(15) -0.00759(15) 0.0611(4) Uani d . 1 . .
H H9 0.7224 0.6238 -0.0119 0.064(5) Uiso calc R 1 . .
C C10 0.50840(18) 0.64191(16) -0.09167(14) 0.0591(4) Uani d . 1 . .
H H10 0.5165 0.6049 -0.1537 0.075(6) Uiso calc R 1 . .
C C11 0.37323(16) 0.68561(14) -0.08648(12) 0.0480(3) Uani d . 1 . .
H H11 0.2897 0.6808 -0.1454 0.071(5) Uiso calc R 1 . .
C C12 0.4945(2) 1.05407(18) 0.25878(13) 0.0681(5) Uani d . 1 . .
H H12A 0.5311 1.0252 0.3306 0.087(6) Uiso calc R 1 . .
H H12B 0.4511 1.1438 0.2553 0.110(8) Uiso calc R 1 . .
H H12C 0.5754 1.0568 0.2292 0.102(8) Uiso calc R 1 . .
C C13 0.25712(19) 0.9411(2) 0.24771(13) 0.0700(5) Uani d . 1 . .
H H13A 0.2988 0.9112 0.3189 0.087(6) Uiso calc R 1 . .
H H13B 0.1853 0.8751 0.2096 0.075(6) Uiso calc R 1 . .
H H13C 0.2092 1.0283 0.2465 0.101(7) Uiso calc R 1 . .
C C14 0.15735(16) 0.98576(16) -0.09356(11) 0.0534(4) Uani d . 1 . .
H H14A 0.0747 0.9367 -0.1396 0.077(6) Uiso calc R 1 . .
H H14B 0.2422 0.9782 -0.1188 0.065(5) Uiso calc R 1 . .
H H14C 0.1311 1.0807 -0.0914 0.068(5) Uiso calc R 1 . .
C C15 0.11358(14) 0.69159(15) 0.00123(11) 0.0478(3) Uani d . 1 . .
O O16 -0.01107(11) 0.71988(13) -0.00265(11) 0.0683(3) Uani d . 1 . .
H H15 0.1438(17) 0.5954(18) -0.0040(12) 0.053(4) Uiso 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
C7 S1 C2 . . 106.85(6) no
C3 C2 C13 . . 112.85(11) no
C3 C2 C12 . . 108.82(12) no
C13 C2 C12 . . 110.29(14) no
C3 C2 S1 . . 112.68(9) no
C13 C2 S1 . . 105.77(11) no
C12 C2 S1 . . 106.22(10) no
C2 C3 C4 . . 118.59(11) no
C2 C3 H3A . . 107.7 no
C4 C3 H3A . . 107.7 no
C2 C3 H3B . . 107.7 no
C4 C3 H3B . . 107.7 no
H3A C3 H3B . . 107.1 no
N5 C4 C3 . . 112.34(9) no
N5 C4 C14 . . 110.39(11) no
C3 C4 C14 . . 110.58(11) no
N5 C4 H4 . . 107.8 no
C3 C4 H4 . . 107.8 no
C14 C4 H4 . . 107.8 no
C15 N5 C6 . . 119.92(11) no
C15 N5 C4 . . 120.48(10) no
C6 N5 C4 . . 119.04(10) no
C11 C6 C7 . . 120.49(12) no
C11 C6 N5 . . 120.31(11) no
C7 C6 N5 . . 119.20(11) no
C6 C7 C8 . . 118.33(13) no
C6 C7 S1 . . 121.95(9) no
C8 C7 S1 . . 119.36(11) no
C9 C8 C7 . . 120.97(14) no
C9 C8 H8 . . 119.5 no
C7 C8 H8 . . 119.5 no
C10 C9 C8 . . 120.10(13) no
C10 C9 H9 . . 120.0 no
C8 C9 H9 . . 120.0 no
C9 C10 C11 . . 120.24(15) no
C9 C10 H10 . . 119.9 no
C11 C10 H10 . . 119.9 no
C6 C11 C10 . . 119.82(14) no
C6 C11 H11 . . 120.1 no
C10 C11 H11 . . 120.1 no
C2 C12 H12A . . 109.5 no
C2 C12 H12B . . 109.5 no
H12A C12 H12B . . 109.5 no
C2 C12 H12C . . 109.5 no
H12A C12 H12C . . 109.5 no
H12B C12 H12C . . 109.5 no
C2 C13 H13A . . 109.5 no
C2 C13 H13B . . 109.5 no
H13A C13 H13B . . 109.5 no
C2 C13 H13C . . 109.5 no
H13A C13 H13C . . 109.5 no
H13B C13 H13C . . 109.5 no
C4 C14 H14A . . 109.5 no
C4 C14 H14B . . 109.5 no
H14A C14 H14B . . 109.5 no
C4 C14 H14C . . 109.5 no
H14A C14 H14C . . 109.5 no
H14B C14 H14C . . 109.5 no
O16 C15 N5 . . 125.27(14) no
O16 C15 H15 . . 121.2(9) no
N5 C15 H15 . . 113.5(9) no
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 C7 . 1.7577(15) no
S1 C2 . 1.8536(13) no
C2 C3 . 1.5203(17) no
C2 C13 . 1.521(2) no
C2 C12 . 1.531(2) no
C3 C4 . 1.5227(17) no
C3 H3A . 0.9900 no
C3 H3B . 0.9900 no
C4 N5 . 1.4741(16) no
C4 C14 . 1.5233(19) no
C4 H4 . 1.0000 no
N5 C15 . 1.3465(16) no
N5 C6 . 1.4274(15) no
C6 C11 . 1.383(2) no
C6 C7 . 1.3955(17) no
C7 C8 . 1.3987(18) no
C8 C9 . 1.376(3) no
C8 H8 . 0.9500 no
C9 C10 . 1.371(2) no
C9 H9 . 0.9500 no
C10 C11 . 1.391(2) no
C10 H10 . 0.9500 no
C11 H11 . 0.9500 no
C12 H12A . 0.9800 no
C12 H12B . 0.9800 no
C12 H12C . 0.9800 no
C13 H13A . 0.9800 no
C13 H13B . 0.9800 no
C13 H13C . 0.9800 no
C14 H14A . 0.9800 no
C14 H14B . 0.9800 no
C14 H14C . 0.9800 no
C15 O16 . 1.2151(17) no
C15 H15 . 1.009(18) no
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
C7 S1 C2 C3 . . . . 7.64(11) no
C7 S1 C2 C13 . . . . 131.37(10) no
C7 S1 C2 C12 . . . . -111.41(11) no
C13 C2 C3 C4 . . . . -50.89(17) no
C12 C2 C3 C4 . . . . -173.65(12) no
S1 C2 C3 C4 . . . . 68.82(13) no
C2 C3 C4 N5 . . . . -55.25(15) no
C2 C3 C4 C14 . . . . -179.07(11) no
C3 C4 N5 C15 . . . . 143.57(12) no
C14 C4 N5 C15 . . . . -92.50(14) no
C3 C4 N5 C6 . . . . -44.92(15) no
C14 C4 N5 C6 . . . . 79.01(13) no
C15 N5 C6 C11 . . . . 66.09(17) no
C4 N5 C6 C11 . . . . -105.47(14) no
C15 N5 C6 C7 . . . . -114.10(14) no
C4 N5 C6 C7 . . . . 74.34(15) no
C11 C6 C7 C8 . . . . 1.25(19) no
N5 C6 C7 C8 . . . . -178.55(11) no
C11 C6 C7 S1 . . . . -171.93(10) no
N5 C6 C7 S1 . . . . 8.26(17) no
C2 S1 C7 C6 . . . . -57.55(12) no
C2 S1 C7 C8 . . . . 129.33(11) no
C6 C7 C8 C9 . . . . -1.8(2) no
S1 C7 C8 C9 . . . . 171.58(11) no
C7 C8 C9 C10 . . . . 0.6(2) no
C8 C9 C10 C11 . . . . 1.2(2) no
C7 C6 C11 C10 . . . . 0.5(2) no
N5 C6 C11 C10 . . . . -179.70(12) no
C9 C10 C11 C6 . . . . -1.8(2) no
C6 N5 C15 O16 . . . . -173.92(15) no
C4 N5 C15 O16 . . . . -2.5(2) no
