#------------------------------------------------------------------------------
#$Date: 2008-01-13 23:15:36 +0100 (Sun, 13 Jan 2008) $
#$Revision: 14 $
#$URL: svn://www.crystallography.net/cod/cif/2/2100391.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_2100391
_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 &
  (3S)-2-benzyl-d~7~-3-phenyl-d~5~-2-azaspiro[3.5]nonane-3,5-d~2~-1-thione
;
_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               99.909(3)
_cell_angle_gamma              90.00
_cell_formula_units_Z          2
_cell_length_a                 8.7075(5)
_cell_length_b                 10.2068(6)
_cell_length_c                 10.0908(9)
_cell_measurement_reflns_used  8684
_cell_measurement_temperature  173(2)
_cell_measurement_theta_max    27.47
_cell_measurement_theta_min    2.05
_cell_volume                   883.45(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  'SHELXS-97 (Sheldrick, 1997)'
_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 0.0379
_diffrn_reflns_av_sigmaI/netI  0.0276
_diffrn_reflns_limit_h_max     11
_diffrn_reflns_limit_h_min     -11
_diffrn_reflns_limit_k_max     13
_diffrn_reflns_limit_k_min     -12
_diffrn_reflns_limit_l_max     13
_diffrn_reflns_limit_l_min     -13
_diffrn_reflns_number          8684
_diffrn_reflns_theta_full      27.47
_diffrn_reflns_theta_max       27.47
_diffrn_reflns_theta_min       2.05
_exptl_absorpt_coefficient_mu  0.183
_exptl_absorpt_correction_T_max 0.9820
_exptl_absorpt_correction_T_min 0.9644
_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  1.208
_exptl_crystal_density_meas    ?
_exptl_crystal_density_method  'not measured'
_exptl_crystal_description     prism
_exptl_crystal_F_000           344
_exptl_crystal_size_max        0.20
_exptl_crystal_size_mid        0.20
_exptl_crystal_size_min        0.10
_refine_diff_density_max       0.392
_refine_diff_density_min       -0.174
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack -0.02(7)
_refine_ls_extinction_coef     0.032(4)
_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 1.062
_refine_ls_hydrogen_treatment  constraint
_refine_ls_matrix_type         full
_refine_ls_number_parameters   270
_refine_ls_number_reflns       3665
_refine_ls_number_restraints   8
_refine_ls_restrained_S_all    1.063
_refine_ls_R_factor_all        0.0436
_refine_ls_R_factor_gt         0.0427
_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^)+(0.0758P)^2^+0.1336P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme    calc
_refine_ls_wR_factor_gt        0.1147
_refine_ls_wR_factor_ref       0.1158
_reflns_number_gt              3573
_reflns_number_total           3665
_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 0.45166(5) 0.95906(4) 0.17436(4) 0.03530(10) Uani d P 0.8519(8) A 1 S
N1 0.63742(16) 1.04679(14) 0.01160(13) 0.0327(3) Uani d PD 0.8519(8) A 1 N
C1 0.62519(17) 0.98356(15) 0.12240(14) 0.0302(3) Uani d P 0.8519(8) A 1 C
C3 0.84274(19) 0.83090(17) 0.16753(16) 0.0384(4) Uani d P 0.8519(8) A 1 C
H3 0.8103 0.7996 0.0785 0.046 Uiso calc PR 0.8519(8) A 1 H
C4 0.9803(2) 0.76316(19) 0.2543(2) 0.0453(4) Uani d P 0.8519(8) A 1 C
H4A 0.9666 0.6671 0.2455 0.054 Uiso calc PR 0.8519(8) A 1 H
H4B 1.0772 0.7867 0.2212 0.054 Uiso calc PR 0.8519(8) A 1 H
C5 0.9965(2) 0.8001(2) 0.3998(2) 0.0472(5) Uani d P 0.8519(8) A 1 C
H5A 0.9197 0.7506 0.4417 0.057 Uiso calc PR 0.8519(8) A 1 H
H5B 1.1021 0.7764 0.4470 0.057 Uiso calc PR 0.8519(8) A 1 H
C6 0.9709(2) 0.9437(2) 0.41482(19) 0.0539(6) Uani d P 0.8519(8) A 1 C
H6A 1.0512 0.9923 0.3762 0.065 Uiso calc PR 0.8519(8) A 1 H
H6B 0.9846 0.9653 0.5118 0.065 Uiso calc PR 0.8519(8) A 1 H
C8 0.79008(18) 1.07354(17) -0.03145(14) 0.0359(3) Uani d P 0.8519(8) A 1 C
H8A 0.7707 1.1152 -0.1214 0.043 Uiso calc PR 0.8519(8) A 1 H
H8B 0.8442 0.9894 -0.0395 0.043 Uiso calc PR 0.8519(8) A 1 H
C9 0.89486(16) 1.16145(16) 0.06513(14) 0.0327(3) Uani d P 0.8519(8) A 1 C
C10 1.04987(18) 1.12689(16) 0.10940(15) 0.0337(3) Uani d P 0.8519(8) A 1 C
H10 1.0904 1.0485 0.0781 0.040 Uiso calc PR 0.8519(8) A 1 H
C11 1.14479(19) 1.20704(19) 0.19909(16) 0.0384(4) Uani d P 0.8519(8) A 1 C
H11 1.2507 1.1834 0.2287 0.046 Uiso calc PR 0.8519(8) A 1 H
C12 1.0876(2) 1.32059(18) 0.24589(16) 0.0389(4) Uani d P 0.8519(8) A 1 C
H12 1.1532 1.3746 0.3083 0.047 Uiso calc PR 0.8519(8) A 1 H
C13 0.9336(2) 1.35564(18) 0.20132(17) 0.0390(4) Uani d P 0.8519(8) A 1 C
H13 0.8932 1.4338 0.2331 0.047 Uiso calc PR 0.8519(8) A 1 H
C14 0.83901(18) 1.27673(17) 0.11068(16) 0.0378(4) Uani d P 0.8519(8) A 1 C
H14 0.7341 1.3020 0.0792 0.045 Uiso calc PR 0.8519(8) A 1 H
C15 0.50096(19) 1.09974(16) -0.08121(14) 0.0361(3) Uani d P 0.8519(8) A 1 C
H15A 0.5180 1.1940 -0.0967 0.043 Uiso calc PR 0.8519(8) A 1 H
H15B 0.4070 1.0916 -0.0388 0.043 Uiso calc PR 0.8519(8) A 1 H
C16 0.47344(17) 1.02921(16) -0.21426(15) 0.0339(3) Uani d P 0.8519(8) A 1 C
C17 0.4916(2) 0.89667(19) -0.22260(17) 0.0401(4) Uani d P 0.8519(8) A 1 C
H17 0.5268 0.8482 -0.1428 0.048 Uiso calc PR 0.8519(8) A 1 H
C18 0.4599(2) 0.8309(2) -0.34522(18) 0.0426(5) Uani d P 0.8519(8) A 1 C
H18 0.4722 0.7386 -0.3492 0.051 Uiso calc PR 0.8519(8) A 1 H
C19 0.4104(2) 0.9020(2) -0.46052(16) 0.0466(5) Uani d P 0.8519(8) A 1 C
H19 0.3904 0.8589 -0.5452 0.056 Uiso calc PR 0.8519(8) A 1 H
C20 0.3896(3) 1.0364(2) -0.45360(17) 0.0525(5) Uani d P 0.8519(8) A 1 C
H20 0.3528 1.0846 -0.5333 0.063 Uiso calc PR 0.8519(8) A 1 H
C21 0.4224(2) 1.1009(2) -0.33068(16) 0.0465(4) Uani d P 0.8519(8) A 1 C
H21 0.4101 1.1932 -0.3262 0.056 Uiso calc PR 0.8519(8) A 1 H
C2 0.76675(14) 0.92910(12) 0.20754(11) 0.0312(3) Uani d D 1 . . C
C7 0.80963(17) 0.99001(14) 0.34634(12) 0.0394(3) Uani d D 1 A . C
H7A 0.7311 0.9652 0.4020 0.047 Uiso calc R 1 B 1 H
H7B 0.8093 1.0867 0.3382 0.047 Uiso calc R 1 B 1 H
S1' 0.4313(4) 0.9398(4) 0.1756(3) 0.0405(7) Uiso d P 0.1481(8) A 2 S
N1' 0.6532(16) 1.0303(13) 0.0228(14) 0.044(4) Uiso d PD 0.1481(8) A 2 N
C1' 0.5930(8) 0.9683(8) 0.1319(6) 0.0127(12) Uiso d P 0.1481(8) A 2 C
C3' 0.7984(7) 0.7801(5) 0.1953(7) 0.0292(16) Uiso d PD 0.1481(8) A 2 C
H3'1 0.7158 0.7294 0.2284 0.035 Uiso calc PR 0.1481(8) A 2 H
H3'2 0.7961 0.7571 0.0996 0.035 Uiso calc PR 0.1481(8) A 2 H
C4' 0.9580(10) 0.7442(14) 0.2775(7) 0.046(7) Uiso d PD 0.1481(8) A 2 C
H4'1 1.0426 0.7796 0.2338 0.055 Uiso calc PR 0.1481(8) A 2 H
H4'2 0.9696 0.6478 0.2839 0.055 Uiso calc PR 0.1481(8) A 2 H
C5' 0.9668(10) 0.8039(5) 0.4185(7) 0.0205(15) Uiso d PD 0.1481(8) A 2 C
H5'1 0.8747 0.7748 0.4562 0.025 Uiso calc PR 0.1481(8) A 2 H
H5'2 1.0608 0.7696 0.4776 0.025 Uiso calc PR 0.1481(8) A 2 H
C6' 0.9728(5) 0.9541(5) 0.4206(5) 0.0262(11) Uiso d PD 0.1481(8) A 2 C
H6'1 0.9911 0.9883 0.5138 0.031 Uiso calc PR 0.1481(8) A 2 H
H6'2 1.0548 0.9877 0.3727 0.031 Uiso calc PR 0.1481(8) A 2 H
C8' 0.8238(10) 1.0011(9) 0.0878(9) 0.0351(17) Uiso d P 0.1481(8) A 2 C
H8' 0.8764 0.9403 0.0320 0.042 Uiso calc PR 0.1481(8) A 2 H
C14' 0.8539(4) 1.2412(5) 0.1673(5) 0.039(2) Uiso d PG 0.1481(8) A 2 C
H14' 0.7442 1.2507 0.1590 0.046 Uiso calc PR 0.1481(8) A 2 H
C9' 0.9162(5) 1.1269(5) 0.1236(6) 0.0322(17) Uiso d PG 0.1481(8) A 2 C
C10' 1.0768(6) 1.1129(5) 0.1357(7) 0.034(2) Uiso d PG 0.1481(8) A 2 C
H10' 1.1194 1.0348 0.1058 0.041 Uiso calc PR 0.1481(8) A 2 H
C11' 1.1751(5) 1.2131(6) 0.1916(6) 0.0144(14) Uiso d PG 0.1481(8) A 2 C
H11' 1.2849 1.2035 0.1999 0.017 Uiso calc PR 0.1481(8) A 2 H
C12' 1.1128(5) 1.3274(6) 0.2354(6) 0.0169(15) Uiso d PG 0.1481(8) A 2 C
H12' 1.1800 1.3959 0.2736 0.020 Uiso calc PR 0.1481(8) A 2 H
C13' 0.9522(5) 1.3414(5) 0.2232(6) 0.040(3) Uiso d PG 0.1481(8) A 2 C
H13' 0.9097 1.4195 0.2532 0.048 Uiso calc PR 0.1481(8) A 2 H
C15' 0.5725(14) 1.1009(13) -0.0730(11) 0.048(2) Uiso d P 0.1481(8) A 2 C
H15C 0.6328 1.1802 -0.0881 0.057 Uiso calc PR 0.1481(8) A 2 H
H15D 0.4743 1.1296 -0.0450 0.057 Uiso calc PR 0.1481(8) A 2 H
C16' 0.5327(6) 1.0182(5) -0.2118(4) 0.0341(19) Uiso d PG 0.1481(8) A 2 C
C17' 0.5117(7) 0.8833(5) -0.2091(5) 0.0232(14) Uiso d PG 0.1481(8) A 2 C
H17' 0.5238 0.8384 -0.1255 0.028 Uiso calc PR 0.1481(8) A 2 H
C18' 0.4731(9) 0.8141(5) -0.3289(6) 0.037(3) Uiso d PG 0.1481(8) A 2 C
H18A 0.4588 0.7218 -0.3271 0.044 Uiso calc PR 0.1481(8) A 2 H
C19' 0.4554(10) 0.8798(7) -0.4512(5) 0.041(3) Uiso d PG 0.1481(8) A 2 C
H19' 0.4290 0.8325 -0.5331 0.061 Uiso calc PR 0.1481(8) A 2 H
C20' 0.4763(9) 1.0147(7) -0.4538(4) 0.041(2) Uiso d PG 0.1481(8) A 2 C
H20' 0.4643 1.0596 -0.5374 0.049 Uiso calc PR 0.1481(8) A 2 H
C21' 0.5150(8) 1.0839(5) -0.3341(5) 0.035(2) Uiso d PG 0.1481(8) A 2 C
H21' 0.5293 1.1761 -0.3359 0.042 Uiso calc PR 0.1481(8) A 2 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 0.03990(17) 0.03442(19) 0.03237(15) 0.00252(15) 0.00850(12) 0.00233(14)
N1 0.0339(6) 0.0343(6) 0.0282(5) -0.0080(5) 0.0007(4) -0.0041(5)
C1 0.0323(6) 0.0296(7) 0.0275(6) -0.0057(5) 0.0016(5) -0.0074(5)
C3 0.0382(7) 0.0384(8) 0.0364(7) 0.0012(7) 0.0002(6) -0.0040(6)
C4 0.0367(7) 0.0399(9) 0.0549(9) 0.0110(7) -0.0039(7) 0.0022(7)
C5 0.0376(8) 0.0524(10) 0.0485(9) -0.0017(7) -0.0015(7) 0.0121(7)
C6 0.0622(10) 0.0548(11) 0.0369(8) -0.0125(9) -0.0130(7) 0.0067(8)
C8 0.0386(7) 0.0432(8) 0.0255(6) -0.0099(6) 0.0042(5) -0.0033(5)
C9 0.0343(6) 0.0376(7) 0.0248(6) -0.0059(6) 0.0006(5) 0.0022(5)
C10 0.0349(6) 0.0341(7) 0.0321(7) -0.0017(6) 0.0060(5) 0.0028(5)
C11 0.0284(6) 0.0514(9) 0.0349(7) -0.0033(7) 0.0042(5) 0.0072(6)
C12 0.0372(7) 0.0452(9) 0.0327(7) -0.0133(7) 0.0017(6) -0.0022(6)
C13 0.0398(7) 0.0370(8) 0.0377(7) 0.0002(7) -0.0004(6) -0.0038(6)
C14 0.0337(6) 0.0412(8) 0.0361(7) -0.0024(6) -0.0007(5) -0.0025(6)
C15 0.0412(7) 0.0342(7) 0.0301(6) 0.0000(7) -0.0014(6) 0.0057(6)
C16 0.0309(6) 0.0377(8) 0.0307(6) -0.0048(6) -0.0013(5) 0.0077(5)
C17 0.0373(7) 0.0463(9) 0.0330(7) -0.0003(7) -0.0044(6) 0.0084(6)
C18 0.0381(8) 0.0444(9) 0.0410(8) -0.0033(7) -0.0053(6) -0.0012(7)
C19 0.0489(9) 0.0602(10) 0.0270(7) -0.0111(9) -0.0039(6) -0.0036(7)
C20 0.0640(11) 0.0560(10) 0.0310(7) -0.0118(9) -0.0102(7) 0.0109(7)
C21 0.0570(9) 0.0451(9) 0.0326(7) -0.0078(8) -0.0061(7) 0.0113(6)
C2 0.0340(5) 0.0311(6) 0.0260(5) -0.0029(5) -0.0020(4) 0.0006(4)
C7 0.0481(7) 0.0411(7) 0.0256(5) -0.0012(6) -0.0033(5) -0.0027(5)
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 . . 122.98(14) no
C1 N1 C8 . . 123.04(13) no
C15 N1 C8 . . 113.98(13) no
N1 C1 C2 . . 119.80(13) no
N1 C1 S1 . . 122.82(11) no
C2 C1 S1 . . 117.38(10) no
C2 C3 C4 . . 124.20(14) no
C2 C3 H3 . . 117.9 no
C4 C3 H3 . . 117.9 no
C5 C4 C3 . . 112.45(16) no
C5 C4 H4A . . 109.1 no
C3 C4 H4A . . 109.1 no
C5 C4 H4B . . 109.1 no
C3 C4 H4B . . 109.1 no
H4A C4 H4B . . 107.8 no
C6 C5 C4 . . 110.82(16) no
C6 C5 H5A . . 109.5 no
C4 C5 H5A . . 109.5 no
C6 C5 H5B . . 109.5 no
C4 C5 H5B . . 109.5 no
H5A C5 H5B . . 108.1 no
C5 C6 C7 . . 113.51(16) no
C5 C6 H6A . . 108.9 no
C7 C6 H6A . . 108.9 no
C5 C6 H6B . . 108.9 no
C7 C6 H6B . . 108.9 no
H6A C6 H6B . . 107.7 no
N1 C8 C9 . . 112.96(12) no
N1 C8 H8A . . 109.0 no
C9 C8 H8A . . 109.0 no
N1 C8 H8B . . 109.0 no
C9 C8 H8B . . 109.0 no
H8A C8 H8B . . 107.8 no
C14 C9 C10 . . 119.10(13) no
C14 C9 C8 . . 120.82(13) no
C10 C9 C8 . . 120.08(14) no
C11 C10 C9 . . 119.81(15) no
C11 C10 H10 . . 120.1 no
C9 C10 H10 . . 120.1 no
C12 C11 C10 . . 120.77(15) no
C12 C11 H11 . . 119.6 no
C10 C11 H11 . . 119.6 no
C11 C12 C13 . . 119.53(15) no
C11 C12 H12 . . 120.2 no
C13 C12 H12 . . 120.2 no
C14 C13 C12 . . 119.87(16) no
C14 C13 H13 . . 120.1 no
C12 C13 H13 . . 120.1 no
C13 C14 C9 . . 120.90(15) no
C13 C14 H14 . . 119.6 no
C9 C14 H14 . . 119.6 no
N1 C15 C16 . . 112.11(14) no
N1 C15 H15A . . 109.2 no
C16 C15 H15A . . 109.2 no
N1 C15 H15B . . 109.2 no
C16 C15 H15B . . 109.2 no
H15A C15 H15B . . 107.9 no
C17 C16 C21 . . 119.51(16) no
C17 C16 C15 . . 121.73(14) no
C21 C16 C15 . . 118.72(15) no
C16 C17 C18 . . 121.64(16) no
C16 C17 H17 . . 119.2 no
C18 C17 H17 . . 119.2 no
C19 C18 C17 . . 118.83(19) no
C19 C18 H18 . . 120.6 no
C17 C18 H18 . . 120.6 no
C18 C19 C20 . . 120.25(17) no
C18 C19 H19 . . 119.9 no
C20 C19 H19 . . 119.9 no
C19 C20 C21 . . 120.32(17) no
C19 C20 H20 . . 119.8 no
C21 C20 H20 . . 119.8 no
C20 C21 C16 . . 119.45(19) no
C20 C21 H21 . . 120.3 no
C16 C21 H21 . . 120.3 no
C3 C2 C1 . . 121.62(12) no
C3 C2 C7 . . 122.90(12) no
C1 C2 C7 . . 115.37(11) no
C7 C2 C3' . . 117.1(3) no
C7 C2 C8' . . 117.3(3) no
C3' C2 C8' . . 108.3(5) no
C7 C2 C1' . . 113.2(3) no
C3' C2 C1' . . 111.6(4) no
C8' C2 C1' . . 85.2(4) no
C2 C7 C6 . . 110.55(13) no
C2 C7 C6' . . 114.4(2) no
C2 C7 H7A . . 109.5 no
C6 C7 H7A . . 109.5 no
C2 C7 H7B . . 109.5 no
C6 C7 H7B . . 109.5 no
H7A C7 H7B . . 108.1 no
C15' N1' C1' . . 125.8(12) no
C15' N1' C8' . . 140.7(13) no
C1' N1' C8' . . 92.3(8) no
N1' C1' S1' . . 139.0(7) no
N1' C1' C2 . . 92.0(6) no
S1' C1' C2 . . 129.0(5) no
C4' C3' C2 . . 110.3(6) no
C4' C3' H3'1 . . 109.6 no
C2 C3' H3'1 . . 109.6 no
C4' C3' H3'2 . . 109.6 no
C2 C3' H3'2 . . 109.6 no
H3'1 C3' H3'2 . . 108.1 no
C3' C4' C5' . . 107.6(7) no
C3' C4' H4'1 . . 110.2 no
C5' C4' H4'1 . . 110.2 no
C3' C4' H4'2 . . 110.2 no
C5' C4' H4'2 . . 110.2 no
H4'1 C4' H4'2 . . 108.5 no
C6' C5' C4' . . 113.9(7) no
C6' C5' H5'1 . . 108.8 no
C4' C5' H5'1 . . 108.8 no
C6' C5' H5'2 . . 108.8 no
C4' C5' H5'2 . . 108.8 no
H5'1 C5' H5'2 . . 107.7 no
C7 C6' C5' . . 101.9(4) no
C7 C6' H6'1 . . 111.4 no
C5' C6' H6'1 . . 111.4 no
C7 C6' H6'2 . . 111.4 no
C5' C6' H6'2 . . 111.4 no
H6'1 C6' H6'2 . . 109.3 no
C9' C8' N1' . . 111.5(8) no
C9' C8' C2 . . 115.9(6) no
N1' C8' C2 . . 90.5(7) no
C9' C8' H8' . . 112.4 no
N1' C8' H8' . . 112.4 no
C2 C8' H8' . . 112.4 no
C9' C14' C13' . . 120.0 no
C9' C14' H14' . . 120.0 no
C13' C14' H14' . . 120.0 no
C14' C9' C10' . . 120.0 no
C14' C9' C8' . . 124.2(4) no
C10' C9' C8' . . 114.6(4) no
C11' C10' C9' . . 120.0 no
C11' C10' H10' . . 120.0 no
C9' C10' H10' . . 120.0 no
C12' C11' C10' . . 120.0 no
C12' C11' H11' . . 120.0 no
C10' C11' H11' . . 120.0 no
C11' C12' C13' . . 120.0 no
C11' C12' H12' . . 120.0 no
C13' C12' H12' . . 120.0 no
C12' C13' C14' . . 120.0 no
C12' C13' H13' . . 120.0 no
C14' C13' H13' . . 120.0 no
N1' C15' C16' . . 111.1(11) no
N1' C15' H15C . . 109.4 no
C16' C15' H15C . . 109.4 no
N1' C15' H15D . . 109.4 no
C16' C15' H15D . . 109.4 no
H15C C15' H15D . . 108.0 no
C17' C16' C21' . . 120.0 no
C17' C16' C15' . . 120.6(5) no
C21' C16' C15' . . 119.4(5) no
C18' C17' C16' . . 120.0 no
C18' C17' H17' . . 120.0 no
C16' C17' H17' . . 120.0 no
C17' C18' C19' . . 120.0 no
C17' C18' H18A . . 120.0 no
C19' C18' H18A . . 120.0 no
C18' C19' C20' . . 120.0 no
C18' C19' H19' . . 120.0 no
C20' C19' H19' . . 120.0 no
C21' C20' C19' . . 120.0 no
C21' C20' H20' . . 120.0 no
C19' C20' H20' . . 120.0 no
C20' C21' C16' . . 120.0 no
C20' C21' H21' . . 120.0 no
C16' C21' H21' . . 120.0 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 . 1.7010(16) no
N1 C1 . 1.311(2) no
N1 C15 . 1.483(2) no
N1 C8 . 1.493(2) no
C1 C2 . 1.4839(18) no
C3 C2 . 1.303(2) no
C3 C4 . 1.523(2) no
C3 H3 . 0.9500 no
C4 C5 . 1.498(3) no
C4 H4A . 0.9900 no
C4 H4B . 0.9900 no
C5 C6 . 1.495(3) no
C5 H5A . 0.9900 no
C5 H5B . 0.9900 no
C6 C7 . 1.529(2) no
C6 H6A . 0.9900 no
C6 H6B . 0.9900 no
C8 C9 . 1.510(2) no
C8 H8A . 0.9900 no
C8 H8B . 0.9900 no
C9 C14 . 1.382(2) no
C9 C10 . 1.392(2) no
C10 C11 . 1.384(2) no
C10 H10 . 0.9500 no
C11 C12 . 1.377(3) no
C11 H11 . 0.9500 no
C12 C13 . 1.386(2) no
C12 H12 . 0.9500 no
C13 C14 . 1.380(2) no
C13 H13 . 0.9500 no
C14 H14 . 0.9500 no
C15 C16 . 1.506(2) no
C15 H15A . 0.9900 no
C15 H15B . 0.9900 no
C16 C17 . 1.366(2) no
C16 C21 . 1.390(2) no
C17 C18 . 1.393(2) no
C17 H17 . 0.9500 no
C18 C19 . 1.376(3) no
C18 H18 . 0.9500 no
C19 C20 . 1.387(3) no
C19 H19 . 0.9500 no
C20 C21 . 1.390(3) no
C20 H20 . 0.9500 no
C21 H21 . 0.9500 no
C2 C7 . 1.5190(16) no
C2 C3' . 1.555(5) no
C2 C8' . 1.566(9) no
C2 C1' . 1.623(7) no
C7 C6' . 1.532(4) no
C7 H7A . 0.9900 no
C7 H7B . 0.9900 no
S1' C1' . 1.573(8) no
N1' C15' . 1.309(16) no
N1' C1' . 1.444(16) no
N1' C8' . 1.546(15) no
C3' C4' . 1.535(7) no
C3' H3'1 . 0.9900 no
C3' H3'2 . 0.9900 no
C4' C5' . 1.537(7) no
C4' H4'1 . 0.9900 no
C4' H4'2 . 0.9900 no
C5' C6' . 1.535(6) no
C5' H5'1 . 0.9900 no
C5' H5'2 . 0.9900 no
C6' H6'1 . 0.9900 no
C6' H6'2 . 0.9900 no
C8' C9' . 1.526(10) no
C8' H8' . 1.0000 no
C14' C9' . 1.3900 no
C14' C13' . 1.3900 no
C14' H14' . 0.9500 no
C9' C10' . 1.3900 no
C10' C11' . 1.3900 no
C10' H10' . 0.9500 no
C11' C12' . 1.3900 no
C11' H11' . 0.9500 no
C12' C13' . 1.3900 no
C12' H12' . 0.9500 no
C13' H13' . 0.9500 no
C15' C16' . 1.621(12) no
C15' H15C . 0.9900 no
C15' H15D . 0.9900 no
C16' C17' . 1.3900 no
C16' C21' . 1.3900 no
C17' C18' . 1.3900 no
C17' H17' . 0.9500 no
C18' C19' . 1.3900 no
C18' H18A . 0.9500 no
C19' C20' . 1.3900 no
C19' H19' . 0.9500 no
C20' C21' . 1.3900 no
C20' H20' . 0.9500 no
C21' H21' . 0.9500 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
C15 N1 C1 C2 . . . . 177.69(13) no
C8 N1 C1 C2 . . . . -3.2(2) no
C15 N1 C1 S1 . . . . -1.8(2) no
C8 N1 C1 S1 . . . . 177.30(12) no
C2 C3 C4 C5 . . . . 13.2(3) no
C3 C4 C5 C6 . . . . -42.3(2) no
C4 C5 C6 C7 . . . . 59.8(2) no
C1 N1 C8 C9 . . . . -63.7(2) no
C15 N1 C8 C9 . . . . 115.49(14) no
N1 C8 C9 C14 . . . . -48.6(2) no
N1 C8 C9 C10 . . . . 131.44(15) no
C14 C9 C10 C11 . . . . 0.8(2) no
C8 C9 C10 C11 . . . . -179.24(14) no
C9 C10 C11 C12 . . . . 0.3(3) no
C10 C11 C12 C13 . . . . -0.7(3) no
C11 C12 C13 C14 . . . . 0.0(3) no
C12 C13 C14 C9 . . . . 1.2(3) no
C10 C9 C14 C13 . . . . -1.6(2) no
C8 C9 C14 C13 . . . . 178.49(15) no
C1 N1 C15 C16 . . . . -112.42(17) no
C8 N1 C15 C16 . . . . 68.38(17) no
N1 C15 C16 C17 . . . . 39.4(2) no
N1 C15 C16 C21 . . . . -143.08(16) no
C21 C16 C17 C18 . . . . -0.2(3) no
C15 C16 C17 C18 . . . . 177.30(15) no
C16 C17 C18 C19 . . . . 0.6(3) no
C17 C18 C19 C20 . . . . -1.3(3) no
C18 C19 C20 C21 . . . . 1.7(3) no
C19 C20 C21 C16 . . . . -1.2(3) no
C17 C16 C21 C20 . . . . 0.5(3) no
C15 C16 C21 C20 . . . . -177.07(18) no
C4 C3 C2 C1 . . . . -174.62(16) no
C4 C3 C2 C7 . . . . 1.4(3) no
C4 C3 C2 C3' . . . . -84.9(5) no
C4 C3 C2 C8' . . . . 119.5(4) no
C4 C3 C2 C1' . . . . -160.7(3) no
N1 C1 C2 C3 . . . . -68.9(2) no
S1 C1 C2 C3 . . . . 110.66(15) no
N1 C1 C2 C7 . . . . 114.79(15) no
S1 C1 C2 C7 . . . . -65.66(15) no
N1 C1 C2 C3' . . . . -100.7(3) no
S1 C1 C2 C3' . . . . 78.9(3) no
N1 C1 C2 C8' . . . . 1.8(4) no
S1 C1 C2 C8' . . . . -178.7(4) no
N1 C1 C2 C1' . . . . -163.1(14) no
S1 C1 C2 C1' . . . . 16.4(13) no
C3 C2 C7 C6 . . . . 13.6(2) no
C1 C2 C7 C6 . . . . -170.16(14) no
C3' C2 C7 C6 . . . . 45.2(3) no
C8' C2 C7 C6 . . . . -86.1(4) no
C1' C2 C7 C6 . . . . 177.1(3) no
C3 C2 C7 C6' . . . . 16.1(3) no
C1 C2 C7 C6' . . . . -167.6(2) no
C3' C2 C7 C6' . . . . 47.7(4) no
C8' C2 C7 C6' . . . . -83.6(5) no
C1' C2 C7 C6' . . . . 179.7(4) no
C5 C6 C7 C2 . . . . -44.0(2) no
C5 C6 C7 C6' . . . . 167(3) no
C15' N1' C1' S1' . . . . 10(2) no
C8' N1' C1' S1' . . . . 179.3(9) no
C15' N1' C1' C2 . . . . -171.1(13) no
C8' N1' C1' C2 . . . . -1.3(7) no
C3 C2 C1' N1' . . . . -77.2(7) no
C1 C2 C1' N1' . . . . 15.9(12) no
C7 C2 C1' N1' . . . . 119.0(6) no
C3' C2 C1' N1' . . . . -106.4(7) no
C8' C2 C1' N1' . . . . 1.3(7) no
C3 C2 C1' S1' . . . . 102.2(6) no
C1 C2 C1' S1' . . . . -164.7(19) no
C7 C2 C1' S1' . . . . -61.5(7) no
C3' C2 C1' S1' . . . . 73.1(7) no
C8' C2 C1' S1' . . . . -179.2(7) no
C3 C2 C3' C4' . . . . 67.2(6) no
C1 C2 C3' C4' . . . . 173.5(5) no
C7 C2 C3' C4' . . . . -42.6(7) no
C8' C2 C3' C4' . . . . 92.8(7) no
C1' C2 C3' C4' . . . . -175.3(6) no
C2 C3' C4' C5' . . . . 49.1(10) no
C3' C4' C5' C6' . . . . -67.9(10) no
C2 C7 C6' C5' . . . . -55.2(4) no
C6 C7 C6' C5' . . . . -23(3) no
C4' C5' C6' C7 . . . . 68.0(7) no
C15' N1' C8' C9' . . . . 50(2) no
C1' N1' C8' C9' . . . . -116.8(8) no
C15' N1' C8' C2 . . . . 168.2(19) no
C1' N1' C8' C2 . . . . 1.4(7) no
C3 C2 C8' C9' . . . . -124.0(6) no
C1 C2 C8' C9' . . . . 110.0(6) no
C7 C2 C8' C9' . . . . -0.6(7) no
C3' C2 C8' C9' . . . . -135.8(6) no
C1' C2 C8' C9' . . . . 113.1(6) no
C3 C2 C8' N1' . . . . 121.6(6) no
C1 C2 C8' N1' . . . . -4.3(6) no
C7 C2 C8' N1' . . . . -114.9(6) no
C3' C2 C8' N1' . . . . 109.9(7) no
C1' C2 C8' N1' . . . . -1.2(7) no
C13' C14' C9' C10' . . . . 0.0 no
C13' C14' C9' C8' . . . . 166.9(6) no
N1' C8' C9' C14' . . . . 34.6(10) no
C2 C8' C9' C14' . . . . -67.0(8) no
N1' C8' C9' C10' . . . . -157.8(7) no
C2 C8' C9' C10' . . . . 100.6(6) no
C14' C9' C10' C11' . . . . 0.0 no
C8' C9' C10' C11' . . . . -168.1(6) no
C9' C10' C11' C12' . . . . 0.0 no
C10' C11' C12' C13' . . . . 0.0 no
C11' C12' C13' C14' . . . . 0.0 no
C9' C14' C13' C12' . . . . 0.0 no
C1' N1' C15' C16' . . . . -102.8(14) no
C8' N1' C15' C16' . . . . 93.4(19) no
N1' C15' C16' C17' . . . . 31.2(13) no
N1' C15' C16' C21' . . . . -150.6(9) no
C21' C16' C17' C18' . . . . 0.0 no
C15' C16' C17' C18' . . . . 178.1(6) no
C16' C17' C18' C19' . . . . 0.0 no
C17' C18' C19' C20' . . . . 0.0 no
C18' C19' C20' C21' . . . . 0.0 no
C19' C20' C21' C16' . . . . 0.0 no
C17' C16' C21' C20' . . . . 0.0 no
C15' C16' C21' C20' . . . . -178.1(6) no