#------------------------------------------------------------------------------
#$Date: 2008-01-13 23:15:36 +0100 (Sun, 13 Jan 2008) $
#$Revision: 14 $
#$URL: svn://www.crystallography.net/cod/cif/2/2100390.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_2100390
_journal_coeditor_code         OG5014
_journal_date_accepted         2005-11-22
_journal_date_recd_electronic  2005-07-29
_journal_issue                 1
_journal_name_full             'Acta Crystallographica, Section B'
_journal_page_first            153
_journal_page_last             160
_journal_paper_category        FA
_journal_volume                62
_journal_year                  2006
_chemical_formula_moiety       'C21 H9 D14 N S'
_chemical_formula_sum          'C21 H9 D14 N S'
_chemical_formula_weight       335.43
_chemical_melting_point        346
_chemical_name_common          N,N-di(benzyl-d~7~)-1-cyclohexenecarbothioamide
_chemical_name_systematic      N,N-di(benzyl-d~7~)-1-cyclohexenecarbothioamide
_symmetry_cell_setting         monoclinic
_symmetry_space_group_name_Hall 'P 2yb'
_symmetry_space_group_name_H-M 'P 21'
_atom_sites_solution_hydrogens geom
_atom_sites_solution_primary   direct
_atom_sites_solution_secondary difmap
_audit_creation_method         'SHELXL-97 and manual editing'
_cell_angle_alpha              90.00
_cell_angle_beta               98.364(4)
_cell_angle_gamma              90.00
_cell_formula_units_Z          2
_cell_length_a                 8.5992(7)
_cell_length_b                 10.1263(7)
_cell_length_c                 10.0412(7)
_cell_measurement_reflns_used  7397
_cell_measurement_temperature  173(2)
_cell_measurement_theta_max    25.34
_cell_measurement_theta_min    2.05
_cell_volume                   865.07(11)
_computing_cell_refinement     'PROCESS-AUTO (Rigaku, 1998)'
_computing_data_collection     'PROCESS-AUTO (Rigaku, 1998)'
_computing_data_reduction      'CrystalStructure 3.6 (Rigaku, 2004)'
_computing_molecular_graphics  'ORTEP-3 for Windows (Farrugia, 1998)'
_computing_publication_material 'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution  'SIR-2004 (Burla, 2005)'
_diffrn_ambient_temperature    173(2)
_diffrn_detector_area_resol_mean 10
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type 'Rigaku RAXIS-RAPID'
_diffrn_measurement_method     '\w scan'
_diffrn_radiation_monochromator graphite
_diffrn_radiation_source       'Rigaku rotating anode Ultrax18'
_diffrn_radiation_type         MoK\a
_diffrn_radiation_wavelength   0.71073
_diffrn_reflns_av_R_equivalents 0.0314
_diffrn_reflns_av_sigmaI/netI  0.0226
_diffrn_reflns_limit_h_max     10
_diffrn_reflns_limit_h_min     -10
_diffrn_reflns_limit_k_max     11
_diffrn_reflns_limit_k_min     -12
_diffrn_reflns_limit_l_max     12
_diffrn_reflns_limit_l_min     -12
_diffrn_reflns_number          7397
_diffrn_reflns_theta_full      25.34
_diffrn_reflns_theta_max       25.34
_diffrn_reflns_theta_min       2.05
_exptl_absorpt_coefficient_mu  0.187
_exptl_absorpt_correction_T_max 0.9816
_exptl_absorpt_correction_T_min 0.9461
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details
;
  ABSCOR, T.Higashi(1995)
  HIGASHI, T. (1995). Abscor - Empirical Absorption Correction
  based on Fourier Series Approximation. Rigaku Corporation,
  Tokyo, Japan.
;
_exptl_crystal_colour          'pale yellow'
_exptl_crystal_density_diffrn  1.234
_exptl_crystal_density_meas    ?
_exptl_crystal_density_method  'not measured'
_exptl_crystal_description     prism
_exptl_crystal_F_000           344
_exptl_crystal_size_max        0.30
_exptl_crystal_size_mid        0.10
_exptl_crystal_size_min        0.10
_refine_diff_density_max       0.160
_refine_diff_density_min       -0.169
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack -0.02(5)
_refine_ls_extinction_coef     0.050(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method   SHELXL
_refine_ls_goodness_of_fit_ref 1.074
_refine_ls_hydrogen_treatment  refall
_refine_ls_matrix_type         full
_refine_ls_number_parameters   301
_refine_ls_number_reflns       2850
_refine_ls_number_restraints   1
_refine_ls_restrained_S_all    1.073
_refine_ls_R_factor_all        0.0278
_refine_ls_R_factor_gt         0.0272
_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/[\s^2^(Fo^2^)+(0.0352P)^2^+0.1521P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme    calc
_refine_ls_wR_factor_gt        0.0616
_refine_ls_wR_factor_ref       0.0619
_reflns_number_gt              2807
_reflns_number_total           2850
_reflns_threshold_expression   >2sigma(I)
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'
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 0.44364(4) 0.95991(4) 0.17728(3) 0.02203(11) Uani d . 1 . . S
N1 0.63270(14) 1.05319(13) 0.01080(12) 0.0187(3) Uani d . 1 . . N
C16 0.47237(17) 1.03036(17) -0.21336(16) 0.0203(3) Uani d . 1 . . C
C17 0.49938(17) 0.89530(17) -0.22062(16) 0.0216(3) Uani d . 1 . . C
C20 0.3858(2) 1.0329(2) -0.45272(17) 0.0295(4) Uani d . 1 . . C
C18 0.46862(18) 0.82915(19) -0.34326(17) 0.0255(4) Uani d . 1 . . C
C9 0.89214(17) 1.16799(16) 0.06403(15) 0.0198(3) Uani d . 1 . . C
C2 0.76109(16) 0.93989(16) 0.21078(14) 0.0194(3) Uani d . 1 . . C
C19 0.41178(19) 0.8983(2) -0.45916(18) 0.0280(4) Uani d . 1 . . C
C15 0.49696(17) 1.10328(18) -0.08056(15) 0.0217(3) Uani d . 1 . . C
C10 1.04763(17) 1.13195(16) 0.10623(15) 0.0210(3) Uani d . 1 . . C
C11 1.14360(17) 1.21243(18) 0.19497(15) 0.0232(3) Uani d . 1 . . C
C21 0.41627(19) 1.09881(19) -0.33034(15) 0.0251(4) Uani d . 1 . . C
C6 0.96030(17) 0.9629(2) 0.41835(15) 0.0253(3) Uani d . 1 . . C
C8 0.78741(18) 1.08095(17) -0.03285(15) 0.0223(3) Uani d . 1 . . C
C4 0.9800(2) 0.77661(19) 0.25875(18) 0.0287(4) Uani d . 1 . . C
C7 0.79850(19) 1.00387(18) 0.34808(16) 0.0238(3) Uani d . 1 . . C
C12 1.08620(18) 1.32701(17) 0.24394(15) 0.0239(3) Uani d . 1 . . C
C13 0.93109(19) 1.36321(18) 0.20215(17) 0.0257(3) Uani d . 1 . . C
C1 0.61716(17) 0.98896(14) 0.12413(14) 0.0187(3) Uani d . 1 . . C
C3 0.84247(18) 0.83902(17) 0.17126(16) 0.0241(3) Uani d . 1 . . C
C14 0.83554(18) 1.28508(17) 0.11120(16) 0.0238(3) Uani d . 1 . . C
C5 0.98485(19) 0.81522(19) 0.40616(17) 0.0289(4) Uani d . 1 . . C
H17 0.5366(19) 0.8470(18) -0.1403(17) 0.014(4) Uiso d . 1 . . H
H20 0.349(2) 1.084(2) -0.531(2) 0.026(5) Uiso d . 1 . . H
H18 0.486(2) 0.731(2) -0.3470(18) 0.024(4) Uiso d . 1 . . H
H19 0.396(2) 0.853(2) -0.544(2) 0.029(5) Uiso d . 1 . . H
H15A 0.5136(19) 1.194(2) -0.0981(16) 0.017(4) Uiso d . 1 . . H
H15B 0.402(2) 1.0882(19) -0.0323(17) 0.022(4) Uiso d . 1 . . H
H10 1.0903(18) 1.0490(18) 0.0756(16) 0.014(4) Uiso d . 1 . . H
H11 1.253(2) 1.1888(19) 0.2269(18) 0.028(5) Uiso d . 1 . . H
H21 0.400(2) 1.193(2) -0.3245(18) 0.028(5) Uiso d . 1 . . H
H6B 0.971(2) 0.988(2) 0.515(2) 0.037(5) Uiso d . 1 . . H
H6A 1.039(2) 1.0059(19) 0.3772(19) 0.028(5) Uiso d . 1 . . H
H8B 0.7643(19) 1.1245(19) -0.1196(18) 0.017(4) Uiso d . 1 . . H
H8A 0.839(2) 0.9954(19) -0.0448(17) 0.020(4) Uiso d . 1 . . H
H4A 1.078(3) 0.808(2) 0.226(2) 0.039(6) Uiso d . 1 . . H
H4B 0.975(2) 0.682(2) 0.246(2) 0.029(5) Uiso d . 1 . . H
H7A 0.717(2) 0.9801(19) 0.4051(17) 0.025(4) Uiso d . 1 . . H
H7B 0.790(2) 1.101(2) 0.3378(19) 0.032(5) Uiso d . 1 . . H
H12 1.155(2) 1.3792(19) 0.3100(17) 0.020(4) Uiso d . 1 . . H
H13 0.889(2) 1.438(2) 0.2380(17) 0.024(4) Uiso d . 1 . . H
H3 0.815(2) 0.802(2) 0.077(2) 0.034(5) Uiso d . 1 . . H
H14 0.727(2) 1.3122(18) 0.0776(17) 0.020(4) Uiso d . 1 . . H
H5A 0.900(2) 0.767(2) 0.447(2) 0.036(5) Uiso d . 1 . . H
H5B 1.094(2) 0.792(2) 0.4573(19) 0.032(5) Uiso d . 1 . . H
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
S1 0.01794(16) 0.0244(2) 0.02414(18) -0.00081(15) 0.00429(12) 0.00096(17)
N1 0.0169(6) 0.0216(7) 0.0170(6) -0.0008(5) 0.0004(4) -0.0003(5)
C16 0.0131(6) 0.0255(9) 0.0218(8) -0.0029(6) 0.0004(5) 0.0030(7)
C17 0.0159(7) 0.0273(9) 0.0204(7) -0.0011(6) -0.0010(6) 0.0033(7)
C20 0.0282(8) 0.0372(11) 0.0213(8) -0.0036(7) -0.0027(6) 0.0072(8)
C18 0.0183(7) 0.0295(10) 0.0285(8) -0.0018(7) 0.0022(6) -0.0038(7)
C9 0.0182(7) 0.0230(8) 0.0184(7) -0.0019(6) 0.0033(5) 0.0032(6)
C2 0.0174(6) 0.0206(8) 0.0199(7) -0.0034(6) 0.0014(5) 0.0013(6)
C19 0.0238(8) 0.0383(10) 0.0214(8) -0.0054(7) 0.0012(6) -0.0041(8)
C15 0.0210(7) 0.0210(9) 0.0221(8) 0.0019(6) -0.0004(6) 0.0015(7)
C10 0.0204(7) 0.0215(9) 0.0217(7) -0.0003(6) 0.0049(6) 0.0024(6)
C11 0.0182(7) 0.0284(9) 0.0225(7) -0.0004(6) 0.0015(6) 0.0060(7)
C21 0.0236(7) 0.0263(10) 0.0244(8) -0.0021(7) -0.0002(6) 0.0044(7)
C6 0.0245(7) 0.0281(8) 0.0214(7) -0.0041(7) -0.0033(6) 0.0022(8)
C8 0.0209(7) 0.0270(9) 0.0197(7) -0.0023(6) 0.0054(6) -0.0013(7)
C4 0.0246(8) 0.0249(9) 0.0357(9) 0.0042(7) 0.0008(6) -0.0001(8)
C7 0.0270(8) 0.0235(9) 0.0199(7) 0.0004(6) -0.0003(6) -0.0006(6)
C12 0.0239(7) 0.0267(9) 0.0204(7) -0.0064(7) 0.0008(6) 0.0017(7)
C13 0.0257(8) 0.0239(9) 0.0279(8) 0.0010(6) 0.0052(6) -0.0026(7)
C1 0.0212(7) 0.0164(9) 0.0183(7) -0.0015(5) 0.0020(5) -0.0045(5)
C3 0.0216(7) 0.0249(9) 0.0254(8) 0.0001(6) 0.0024(6) -0.0023(7)
C14 0.0190(7) 0.0264(9) 0.0262(8) 0.0004(6) 0.0033(6) 0.0003(7)
C5 0.0236(8) 0.0303(9) 0.0305(8) 0.0003(7) -0.0039(6) 0.0070(7)
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C1 N1 C15 . . 122.20(13) no
C1 N1 C8 . . 123.27(12) no
C15 N1 C8 . . 114.53(12) no
C21 C16 C17 . . 119.12(17) no
C21 C16 C15 . . 119.28(16) no
C17 C16 C15 . . 121.56(16) no
C16 C17 C18 . . 120.49(17) no
C16 C17 H17 . . 119.7(11) no
C18 C17 H17 . . 119.8(11) no
C19 C20 C21 . . 120.23(18) no
C19 C20 H20 . . 121.8(12) no
C21 C20 H20 . . 117.9(12) no
C19 C18 C17 . . 119.86(19) no
C19 C18 H18 . . 120.3(10) no
C17 C18 H18 . . 119.9(10) no
C14 C9 C10 . . 119.23(14) no
C14 C9 C8 . . 120.77(14) no
C10 C9 C8 . . 120.00(15) no
C3 C2 C1 . . 120.64(13) no
C3 C2 C7 . . 123.25(13) no
C1 C2 C7 . . 115.91(13) no
C20 C19 C18 . . 119.90(18) no
C20 C19 H19 . . 120.4(12) no
C18 C19 H19 . . 119.6(12) no
N1 C15 C16 . . 112.29(13) no
N1 C15 H15A . . 108.9(10) no
C16 C15 H15A . . 108.4(10) no
N1 C15 H15B . . 105.8(10) no
C16 C15 H15B . . 109.1(10) no
H15A C15 H15B . . 112.6(15) no
C11 C10 C9 . . 119.81(15) no
C11 C10 H10 . . 119.2(9) no
C9 C10 H10 . . 121.0(9) no
C12 C11 C10 . . 120.85(14) no
C12 C11 H11 . . 117.7(11) no
C10 C11 H11 . . 121.4(11) no
C16 C21 C20 . . 120.39(18) no
C16 C21 H21 . . 118.5(11) no
C20 C21 H21 . . 121.2(11) no
C5 C6 C7 . . 111.06(14) no
C5 C6 H6B . . 109.4(13) no
C7 C6 H6B . . 109.6(12) no
C5 C6 H6A . . 107.6(12) no
C7 C6 H6A . . 109.4(11) no
H6B C6 H6A . . 109.7(16) no
N1 C8 C9 . . 113.32(12) no
N1 C8 H8B . . 106.0(10) no
C9 C8 H8B . . 109.8(11) no
N1 C8 H8A . . 107.8(10) no
C9 C8 H8A . . 110.7(10) no
H8B C8 H8A . . 109.0(14) no
C3 C4 C5 . . 111.51(14) no
C3 C4 H4A . . 107.4(13) no
C5 C4 H4A . . 109.6(12) no
C3 C4 H4B . . 109.1(12) no
C5 C4 H4B . . 112.0(12) no
H4A C4 H4B . . 107.2(18) no
C2 C7 C6 . . 111.34(13) no
C2 C7 H7A . . 110.1(10) no
C6 C7 H7A . . 109.9(10) no
C2 C7 H7B . . 109.1(11) no
C6 C7 H7B . . 111.4(11) no
H7A C7 H7B . . 104.7(16) no
C11 C12 C13 . . 119.50(15) no
C11 C12 H12 . . 119.1(11) no
C13 C12 H12 . . 121.4(11) no
C14 C13 C12 . . 120.03(17) no
C14 C13 H13 . . 119.7(10) no
C12 C13 H13 . . 120.2(10) no
N1 C1 C2 . . 118.85(12) no
N1 C1 S1 . . 124.02(11) no
C2 C1 S1 . . 117.13(10) no
C2 C3 C4 . . 123.41(14) no
C2 C3 H3 . . 120.2(12) no
C4 C3 H3 . . 116.4(12) no
C13 C14 C9 . . 120.55(15) no
C13 C14 H14 . . 120.6(11) no
C9 C14 H14 . . 118.8(11) no
C6 C5 C4 . . 110.26(14) no
C6 C5 H5A . . 108.9(13) no
C4 C5 H5A . . 110.4(12) no
C6 C5 H5B . . 108.0(12) no
C4 C5 H5B . . 108.7(11) no
H5A C5 H5B . . 110.5(16) 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 C1 . 1.6821(15) no
N1 C1 . 1.3342(19) no
N1 C15 . 1.4662(19) no
N1 C8 . 1.4868(18) no
C16 C21 . 1.389(2) no
C16 C17 . 1.391(2) no
C16 C15 . 1.512(2) no
C17 C18 . 1.393(2) no
C17 H17 . 0.958(17) no
C20 C19 . 1.384(3) no
C20 C21 . 1.390(2) no
C20 H20 . 0.96(2) no
C18 C19 . 1.385(3) no
C18 H18 . 1.00(2) no
C9 C14 . 1.391(2) no
C9 C10 . 1.391(2) no
C9 C8 . 1.510(2) no
C2 C3 . 1.331(2) no
C2 C1 . 1.4908(19) no
C2 C7 . 1.515(2) no
C19 H19 . 0.96(2) no
C15 H15A . 0.953(19) no
C15 H15B . 1.021(18) no
C10 C11 . 1.388(2) no
C10 H10 . 0.984(18) no
C11 C12 . 1.379(3) no
C11 H11 . 0.981(19) no
C21 H21 . 0.96(2) no
C6 C5 . 1.518(3) no
C6 C7 . 1.523(2) no
C6 H6B . 0.99(2) no
C6 H6A . 0.95(2) no
C8 H8B . 0.970(18) no
C8 H8A . 0.988(19) no
C4 C3 . 1.506(2) no
C4 C5 . 1.526(3) no
C4 H4A . 1.00(2) no
C4 H4B . 0.96(2) no
C7 H7A . 0.999(18) no
C7 H7B . 0.99(2) no
C12 C13 . 1.388(2) no
C12 H12 . 0.976(18) no
C13 C14 . 1.385(2) no
C13 H13 . 0.94(2) no
C3 H3 . 1.02(2) no
C14 H14 . 0.980(18) no
C5 H5A . 1.01(2) no
C5 H5B . 1.03(2) 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
C21 C16 C17 C18 . . . . -0.9(2) no
C15 C16 C17 C18 . . . . 176.87(14) no
C16 C17 C18 C19 . . . . 0.5(2) no
C21 C20 C19 C18 . . . . -0.1(3) no
C17 C18 C19 C20 . . . . 0.0(3) no
C1 N1 C15 C16 . . . . -112.01(15) no
C8 N1 C15 C16 . . . . 68.48(18) no
C21 C16 C15 N1 . . . . -145.29(15) no
C17 C16 C15 N1 . . . . 37.0(2) no
C14 C9 C10 C11 . . . . 0.4(2) no
C8 C9 C10 C11 . . . . 179.81(14) no
C9 C10 C11 C12 . . . . 1.1(2) no
C17 C16 C21 C20 . . . . 0.8(2) no
C15 C16 C21 C20 . . . . -177.01(15) no
C19 C20 C21 C16 . . . . -0.3(3) no
C1 N1 C8 C9 . . . . -62.2(2) no
C15 N1 C8 C9 . . . . 117.27(15) no
C14 C9 C8 N1 . . . . -49.3(2) no
C10 C9 C8 N1 . . . . 131.23(15) no
C3 C2 C7 C6 . . . . 14.3(2) no
C1 C2 C7 C6 . . . . -170.77(14) no
C5 C6 C7 C2 . . . . -45.25(18) no
C10 C11 C12 C13 . . . . -1.0(2) no
C11 C12 C13 C14 . . . . -0.5(2) no
C15 N1 C1 C2 . . . . 179.33(14) no
C8 N1 C1 C2 . . . . -1.2(2) no
C15 N1 C1 S1 . . . . -1.1(2) no
C8 N1 C1 S1 . . . . 178.39(12) no
C3 C2 C1 N1 . . . . -70.75(19) no
C7 C2 C1 N1 . . . . 114.16(15) no
C3 C2 C1 S1 . . . . 109.63(14) no
C7 C2 C1 S1 . . . . -65.46(16) no
C1 C2 C3 C4 . . . . -174.28(15) no
C7 C2 C3 C4 . . . . 0.4(3) no
C5 C4 C3 C2 . . . . 16.0(2) no
C12 C13 C14 C9 . . . . 1.9(2) no
C10 C9 C14 C13 . . . . -1.9(2) no
C8 C9 C14 C13 . . . . 178.68(15) no
C7 C6 C5 C4 . . . . 62.94(18) no
C3 C4 C5 C6 . . . . -46.56(19) no