data_2100392
_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 &
  (3R,5R)-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               102.589(8)
_cell_angle_gamma              90.00
_cell_formula_units_Z          2
_cell_length_a                 8.9117(11)
_cell_length_b                 10.5512(17)
_cell_length_c                 10.3463(13)
_cell_measurement_reflns_used  1880
_cell_measurement_temperature  293(2)
_cell_measurement_theta_max    49.05
_cell_measurement_theta_min    5.83
_cell_volume                   949.5(2)
_computing_cell_refinement     'HKL (Otwinowski & Minor, 1997)'
_computing_data_collection     'local program'
_computing_data_reduction      'HKL (Otwinowski & Minor, 1997)'
_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  'Initial structure determined by X-rays'
_diffrn_ambient_temperature    293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.773
_diffrn_measured_fraction_theta_max 0.773
_diffrn_measurement_device_type BIX-III
_diffrn_measurement_method     '\w scan'
_diffrn_radiation_monochromator 'perfect silicon crystal'
_diffrn_radiation_source       'JAERI JRR-3M reactor'
_diffrn_radiation_type         neutron
_diffrn_radiation_wavelength   1.51000
_diffrn_reflns_av_R_equivalents 0.0436
_diffrn_reflns_av_sigmaI/netI  0.0412
_diffrn_reflns_limit_h_max     8
_diffrn_reflns_limit_h_min     -8
_diffrn_reflns_limit_k_max     10
_diffrn_reflns_limit_k_min     -10
_diffrn_reflns_limit_l_max     10
_diffrn_reflns_limit_l_min     -10
_diffrn_reflns_number          1880
_diffrn_reflns_theta_full      49.05
_diffrn_reflns_theta_max       49.05
_diffrn_reflns_theta_min       5.83
_exptl_absorpt_coefficient_mu  0.206
_exptl_absorpt_correction_T_max 0.78400
_exptl_absorpt_correction_T_min 0.59078
_exptl_absorpt_correction_type Gaussian
_exptl_absorpt_process_details
;
  ABSG in PLATON, Crystallographic Computing (1970)
  originally coded by P. Coppens
;
_exptl_crystal_colour          'pale yellow'
_exptl_crystal_density_diffrn  1.173
_exptl_crystal_density_meas    ?
_exptl_crystal_density_method  'not measured'
_exptl_crystal_description     prism
_exptl_crystal_F_000           42
_exptl_crystal_size_max        4.50
_exptl_crystal_size_mid        1.50
_exptl_crystal_size_min        1.40
_refine_diff_density_max       0.044
_refine_diff_density_min       -0.044
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack 0(10)
_refine_ls_extinction_coef     ?
_refine_ls_extinction_method   none
_refine_ls_goodness_of_fit_ref 1.079
_refine_ls_hydrogen_treatment  mixed
_refine_ls_matrix_type         full
_refine_ls_number_parameters   297
_refine_ls_number_reflns       1301
_refine_ls_number_restraints   25
_refine_ls_restrained_S_all    1.072
_refine_ls_R_factor_all        0.0793
_refine_ls_R_factor_gt         0.0792
_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^)+(0.1086P)^2^+0.1004P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme    calc
_refine_ls_wR_factor_gt        0.1967
_refine_ls_wR_factor_ref       0.1967
_reflns_number_gt              1300
_reflns_number_total           1301
_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' 0.9320(10) 0.7798(14) 0.1582(12) 0.6(5) Uiso d PG 0.240(6) A 1 S
N1' 1.1626(9) 0.8489(11) 0.0426(9) 0.034(5) Uiso d PG 0.240(6) A 1 N
C1' 1.1062(10) 0.7892(12) 0.1353(10) 0.093(15) Uiso d PG 0.240(6) A 1 C
C2' 1.2640(10) 0.7438(12) 0.1973(10) 0.11(3) Uiso d PG 0.240(6) A 1 C
C3' 1.2824(13) 0.5977(12) 0.1905(13) 0.085(13) Uiso d PGD 0.240(6) A 1 C
C4' 1.4454(15) 0.5575(13) 0.2512(15) 0.16(3) Uiso d PG 0.240(6) A 1 C
H4A' 1.5236 0.5997 0.1955 0.198 Uiso calc PR 0.240(6) A 1 H
H4B' 1.4546 0.4546 0.2449 0.198 Uiso calc PR 0.240(6) A 1 H
C5' 1.4929(15) 0.5987(16) 0.3970(14) 0.13(3) Uiso d PG 0.240(6) A 1 C
H5A' 1.4219 0.5494 0.4547 0.08(3) Uiso calc PR 0.240(6) A 1 H
H5B' 1.6126 0.5725 0.4365 0.14(6) Uiso calc PR 0.240(6) A 1 H
C6' 1.4747(13) 0.7378(16) 0.4103(11) 0.11(2) Uiso d PG 0.240(6) A 1 C
H6A' 1.5651 0.7848 0.3718 0.11(4) Uiso calc PR 0.240(6) A 1 H
H6B' 1.4938 0.7604 0.5156 0.14(5) Uiso calc PR 0.240(6) A 1 H
C7' 1.3181(12) 0.7953(14) 0.3399(9) 0.08(2) Uiso d PG 0.240(6) A 1 C
H7A' 1.2318 0.7729 0.3969 0.08(2) Uiso calc PR 0.240(6) A 1 H
H7B' 1.3285 0.8983 0.3365 0.043(13) Uiso calc PR 0.240(6) A 1 H
C8' 1.3241(9) 0.8203(11) 0.0932(9) 0.093(12) Uiso d PG 0.240(6) A 1 C
C9' 1.4255(9) 0.9345(12) 0.1329(10) 0.059(8) Uiso d PG 0.240(6) A 1 C
C10' 1.5831(9) 0.9214(14) 0.1442(11) 0.087(13) Uiso d PG 0.240(6) A 1 C
C11' 1.6809(11) 1.0226(16) 0.1909(13) 0.11(2) Uiso d PG 0.240(6) A 1 C
C12' 1.6212(14) 1.1368(15) 0.2262(14) 0.12(2) Uiso d PG 0.240(6) A 1 C
C13' 1.4636(15) 1.1499(13) 0.2149(13) 0.8(4) Uiso d PG 0.240(6) A 1 C
C14' 1.3658(12) 1.0488(12) 0.1682(10) 0.096(14) Uiso d PG 0.240(6) A 1 C
C15' 1.0791(10) 0.9305(12) -0.0666(9) 0.085(14) Uiso d PG 0.240(6) A 1 C
C16' 1.0465(11) 0.8587(13) -0.1987(9) 0.058(9) Uiso d PG 0.240(6) A 1 C
C17' 0.9882(11) 0.7353(14) -0.2035(11) 0.083(14) Uiso d PG 0.240(6) A 1 C
C18' 0.9483(14) 0.6715(16) -0.3240(12) 0.16(3) Uiso d PG 0.240(6) A 1 C
C19' 0.9667(16) 0.7312(19) -0.4397(11) 0.21(4) Uiso d PG 0.240(6) A 1 C
C20' 1.0251(15) 0.8547(19) -0.4349(9) 0.097(13) Uiso d PG 0.240(6) A 1 C
C21' 1.0651(13) 0.9184(16) -0.3143(9) 0.085(11) Uiso d PG 0.240(6) A 1 C
D10' 1.6296(9) 0.8324(15) 0.1167(12) 0.075(11) Uiso d PG 0.240(6) A 1 D
D11' 1.8036(11) 1.0124(19) 0.1997(15) 0.111(17) Uiso d PG 0.240(6) A 1 D
D12' 1.6974(17) 1.2156(17) 0.2626(16) 0.067(10) Uiso d PG 0.240(6) A 1 D
D13' 1.4171(18) 1.2389(13) 0.2425(15) 0.12(2) Uiso d PG 0.240(6) A 1 D
D14' 1.2431(12) 1.0590(11) 0.1594(10) 0.102(14) Uiso d PG 0.240(6) A 1 D
D17' 0.9738(11) 0.6888(13) -0.1134(12) 0.063(9) Uiso d PG 0.240(6) A 1 D
D18' 0.9029(16) 0.5753(17) -0.3278(14) 0.17(3) Uiso d PG 0.240(6) A 1 D
D19' 0.9356(19) 0.682(2) -0.5336(12) 0.30(8) Uiso d PG 0.240(6) A 1 D
D20' 1.0394(18) 0.901(2) -0.5250(9) 0.15(2) Uiso d PG 0.240(6) A 1 D
D21' 1.1107(14) 1.0145(16) -0.3105(10) 0.14(2) Uiso d PG 0.240(6) A 1 D
D8' 1.3646(9) 0.7643(12) 0.0329(10) 0.081(12) Uiso d PG 0.240(6) A 1 D
D15C 0.9707(10) 0.9617(12) -0.0440(10) 0.030(7) Uiso d PG 0.240(6) A 1 D
D15D 1.1477(11) 1.0153(11) -0.0749(10) 0.084(10) Uiso d PG 0.240(6) A 1 D
D3' 1.267(4) 0.573(4) 0.095(3) 0.065(9) Uiso d PD 0.240(6) A 1 D
H3' 1.232(5) 0.521(4) 0.229(4) 0.047(11) Uiso d PD 0.240(6) A 1 H
S1 0.9566(4) 0.7722(6) 0.1700(6) 0.045(4) Uiso d PG 0.760(6) A 2 S
N1 1.1479(5) 0.8519(5) 0.0095(4) 0.068(3) Uani d PG 0.760(6) A 2 N
C1 1.1286(4) 0.7942(4) 0.1208(4) 0.054(3) Uani d PG 0.760(6) A 2 C
C2 1.2750(4) 0.7385(5) 0.2045(4) 0.048(4) Uani d PGD 0.760(6) A 2 C
C3 1.3288(6) 0.6299(5) 0.1689(5) 0.097(5) Uani d PGD 0.760(6) A 2 C
C4 1.4729(7) 0.5666(6) 0.2530(6) 0.119(8) Uani d PGD 0.760(6) A 2 C
H4A 1.5721 0.5906 0.2118 0.121(9) Uiso calc PR 0.760(6) A 2 H
H4B 1.4584 0.4638 0.2473 0.23(2) Uiso calc PR 0.760(6) A 2 H
C5 1.5055(7) 0.6081(8) 0.4012(5) 0.105(8) Uani d PGD 0.760(6) A 2 C
H5A 1.4250 0.5605 0.4510 0.20(3) Uiso calc PR 0.760(6) A 2 H
H5B 1.6218 0.5798 0.4502 0.21(3) Uiso calc PR 0.760(6) A 2 H
C6 1.4889(6) 0.7508(7) 0.4128(4) 0.093(7) Uani d PGD 0.760(6) A 2 C
H6A 1.5688 0.7995 0.3633 0.15(2) Uiso calc PRD 0.760(6) A 2 H
H6B 1.5147 0.7790 0.5169 0.150(17) Uiso calc PRD 0.760(6) A 2 H
C7 1.3211(6) 0.7866(6) 0.3468(4) 0.087(8) Uani d PGD 0.760(6) A 2 C
H7A 1.2437 0.7464 0.4045 0.18(2) Uiso calc PR 0.760(6) A 2 H
H7B 1.3088 0.8895 0.3473 0.159(18) Uiso calc PR 0.760(6) A 2 H
C8 1.2896(6) 0.8769(6) -0.0201(5) 0.080(4) Uani d PGD 0.760(6) A 2 C
C14 1.3472(5) 1.0824(4) 0.1122(5) 0.096(4) Uani d PGD 0.760(6) A 2 C
C9 1.4036(6) 0.9705(5) 0.0702(5) 0.072(3) Uani d PG 0.760(6) A 2 C
C10 1.5580(6) 0.9393(6) 0.1137(8) 0.073(3) Uiso d PGD 0.760(6) A 2 C
C11 1.6558(5) 1.0200(7) 0.1991(8) 0.099(6) Uani d PGD 0.760(6) A 2 C
C12 1.5993(7) 1.1320(6) 0.2411(6) 0.086(5) Uani d PGD 0.760(6) A 2 C
C13 1.4450(7) 1.1631(5) 0.1977(7) 0.067(3) Uani d PGD 0.760(6) A 2 C
C15 1.0001(7) 0.9035(9) -0.0857(10) 0.077(4) Uani d PGD 0.760(6) A 2 C
C21 0.9528(5) 0.9190(4) -0.3268(4) 0.121(6) Uani d PGD 0.760(6) A 2 C
C16 0.9868(4) 0.8444(4) -0.2135(3) 0.075(3) Uani d PG 0.760(6) A 2 C
C17 0.9872(5) 0.7131(4) -0.2244(4) 0.084(5) Uani d PGD 0.760(6) A 2 C
C18 0.9534(6) 0.6564(4) -0.3486(5) 0.083(5) Uani d PGD 0.760(6) A 2 C
C19 0.9193(7) 0.7310(5) -0.4620(4) 0.098(5) Uani d PGD 0.760(6) A 2 C
C20 0.9190(7) 0.8623(5) -0.4511(3) 0.145(7) Uani d PG 0.760(6) A 2 C
D8A 1.2702(4) 0.9238(4) -0.1160(4) 0.101(4) Uani d PG 0.760(6) A 2 D
D8B 1.3588(5) 0.7909(5) -0.0224(5) 0.104(5) Uani d PGD 0.760(6) A 2 D
D10 1.5991(5) 0.8496(7) 0.0825(7) 0.120(6) Uani d PGD 0.760(6) A 2 D
D11 1.7759(6) 0.9940(9) 0.2368(9) 0.181(11) Uani d PGD 0.760(6) A 2 D
D12 1.6626(8) 1.1998(8) 0.3123(9) 0.179(11) Uani d PGD 0.760(6) A 2 D
D13 1.3964(8) 1.2438(7) 0.2379(7) 0.220(19) Uani d PGD 0.760(6) A 2 D
D14 1.2262(6) 1.1057(5) 0.0828(5) 0.114(6) Uani d PGD 0.760(6) A 2 D
D15A 0.9062(5) 0.8974(6) -0.0323(4) 0.101(5) Uani d PGD 0.760(6) A 2 D
D15B 1.0331(5) 1.0027(4) -0.0848(4) 0.094(5) Uani d PGD 0.760(6) A 2 D
D17 1.0281(6) 0.6510(4) -0.1401(5) 0.134(6) Uani d PGD 0.760(6) A 2 D
D18 0.9455(7) 0.5527(4) -0.3506(6) 0.109(5) Uani d PGD 0.760(6) A 2 D
D19 0.8936(8) 0.6766(6) -0.5532(5) 0.222(17) Uani d PGD 0.760(6) A 2 D
D20 0.9051(8) 0.9014(6) -0.5437(3) 0.27(2) Uani d PG 0.760(6) A 2 D
D21 0.9628(6) 1.0216(4) -0.3198(4) 0.26(2) Uani d PGD 0.760(6) A 2 D
H3 1.2905 0.6012 0.0672 0.135(15) Uiso d PGD 0.760(6) 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
N1 0.057(4) 0.090(6) 0.055(4) 0.002(4) 0.008(3) 0.001(4)
C1 0.046(4) 0.066(7) 0.041(5) 0.008(5) -0.006(4) -0.006(5)
C2 0.063(6) 0.028(6) 0.044(6) -0.004(4) -0.010(4) -0.001(4)
C3 0.108(9) 0.056(8) 0.097(9) 0.028(8) -0.042(8) -0.009(8)
C4 0.090(9) 0.048(7) 0.193(19) 0.048(7) -0.027(9) -0.027(9)
C5 0.144(15) 0.075(10) 0.065(8) -0.006(8) -0.046(8) 0.023(7)
C6 0.102(9) 0.044(7) 0.102(11) -0.022(6) -0.042(7) 0.014(7)
C7 0.090(10) 0.128(16) 0.036(6) -0.008(8) 0.000(5) -0.007(7)
C8 0.081(8) 0.094(10) 0.054(6) 0.006(6) -0.010(6) 0.016(7)
C14 0.057(6) 0.064(8) 0.168(13) 0.010(6) 0.026(7) -0.030(10)
C9 0.048(5) 0.078(8) 0.080(7) -0.022(5) -0.009(5) 0.020(7)
C11 0.083(8) 0.108(13) 0.109(11) 0.007(8) 0.029(7) -0.018(9)
C12 0.082(9) 0.103(12) 0.058(7) -0.032(8) -0.018(6) -0.001(7)
C13 0.106(8) 0.049(6) 0.049(5) -0.033(7) 0.024(5) -0.043(6)
C15 0.125(11) 0.023(6) 0.079(9) -0.012(6) 0.011(7) 0.016(7)
C21 0.201(16) 0.142(14) 0.005(5) -0.041(12) -0.013(6) -0.019(7)
C16 0.094(7) 0.099(10) 0.021(5) -0.017(7) -0.009(4) 0.006(6)
C17 0.075(7) 0.064(9) 0.120(12) 0.000(6) 0.033(7) 0.022(9)
C18 0.089(8) 0.089(10) 0.066(7) -0.015(7) 0.009(5) -0.052(9)
C19 0.123(10) 0.090(12) 0.071(9) 0.001(8) 0.000(7) 0.008(9)
C20 0.201(19) 0.123(15) 0.088(11) -0.055(14) -0.021(10) 0.060(12)
D8A 0.114(9) 0.109(11) 0.078(7) -0.055(8) 0.019(7) -0.009(8)
D8B 0.060(7) 0.152(14) 0.111(10) -0.038(8) 0.040(6) -0.050(11)
D10 0.095(9) 0.099(11) 0.163(14) 0.035(9) 0.019(9) 0.034(12)
D11 0.093(10) 0.158(19) 0.26(3) 0.051(11) -0.032(14) -0.047(17)
D12 0.148(15) 0.27(3) 0.116(14) -0.068(18) 0.018(12) -0.004(16)
D13 0.26(3) 0.26(4) 0.106(15) -0.03(3) -0.018(16) -0.081(19)
D14 0.084(8) 0.076(9) 0.169(15) 0.045(7) 0.000(8) -0.030(10)
D15A 0.096(8) 0.137(14) 0.076(7) -0.017(8) 0.030(6) 0.022(8)
D15B 0.080(7) 0.151(16) 0.052(6) -0.011(9) 0.018(5) 0.009(8)
D17 0.179(16) 0.084(12) 0.129(13) 0.048(12) 0.008(12) -0.008(10)
D18 0.129(10) 0.076(9) 0.109(10) -0.007(9) -0.005(8) -0.065(10)
D19 0.177(17) 0.41(5) 0.070(10) 0.00(2) 0.009(10) -0.133(18)
D20 0.54(7) 0.15(2) 0.066(10) -0.01(3) -0.046(19) 0.040(12)
D21 0.58(7) 0.057(11) 0.101(14) -0.02(2) 0.00(2) -0.003(12)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0000 0.0000 'International Tables Vol C Tables 4.4.4.1'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.4.4.1'
N N 0.0000 0.0000 'International Tables Vol C Tables 4.4.4.1'
S S 0.0000 0.0000 'International Tables Vol C Tables 4.4.4.1'
D D 0.0000 0.0000 'International Tables Vol C Tables 4.4.4.1'
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' C8' . . 98.1 no
C1' N1' C15' . . 128.0 no
C8' N1' C15' . . 133.5 no
N1' C1' C2' . . 89.6 no
N1' C1' S1' . . 130.9 no
C2' C1' S1' . . 139.5 no
C1' C2' C8' . . 88.3 no
C1' C2' C7' . . 111.4 no
C8' C2' C7' . . 113.7 no
C1' C2' C3' . . 113.5 no
C8' C2' C3' . . 115.7 no
C7' C2' C3' . . 112.2 no
D3' C3' C4' . . 104.3(18) no
D3' C3' C2' . . 108(2) no
C4' C3' C2' . . 111.2 no
D3' C3' H3' . . 102(4) no
C4' C3' H3' . . 95(2) no
C2' C3' H3' . . 134(3) no
C3' C4' C5' . . 111.2 no
C3' C4' H4A' . . 109.4 no
C5' C4' H4A' . . 109.4 no
C3' C4' H4B' . . 109.4 no
C5' C4' H4B' . . 109.4 no
H4A' C4' H4B' . . 108.0 no
C6' C5' C4' . . 111.0 no
C6' C5' H5A' . . 109.4 no
C4' C5' H5A' . . 109.4 no
C6' C5' H5B' . . 109.4 no
C4' C5' H5B' . . 109.4 no
H5A' C5' H5B' . . 108.0 no
C5' C6' C7' . . 116.6 no
C5' C6' H6A' . . 108.1 no
C7' C6' H6A' . . 108.1 no
C5' C6' H6B' . . 108.1 no
C7' C6' H6B' . . 108.1 no
H6A' C6' H6B' . . 107.3 no
C2' C7' C6' . . 111.8 no
C2' C7' H7A' . . 109.3 no
C6' C7' H7A' . . 109.3 no
C2' C7' H7B' . . 109.3 no
C6' C7' H7B' . . 109.3 no
H7A' C7' H7B' . . 107.9 no
D8' C8' N1' . . 111.6 no
D8' C8' C9' . . 111.8 no
N1' C8' C9' . . 114.9 no
D8' C8' C2' . . 111.3 no
N1' C8' C2' . . 83.8 no
C9' C8' C2' . . 120.6 no
C10' C9' C14' . . 119.9 no
C10' C9' C8' . . 118.5 no
C14' C9' C8' . . 121.4 no
D10' C10' C9' . . 119.9 no
D10' C10' C11' . . 120.3 no
C9' C10' C11' . . 119.8 no
D11' C11' C10' . . 119.8 no
D11' C11' C12' . . 119.9 no
C10' C11' C12' . . 120.3 no
D12' C12' C13' . . 119.8 no
D12' C12' C11' . . 120.3 no
C13' C12' C11' . . 119.9 no
D13' C13' C12' . . 119.9 no
D13' C13' C14' . . 120.3 no
C12' C13' C14' . . 119.8 no
D14' C14' C13' . . 119.8 no
D14' C14' C9' . . 119.9 no
C13' C14' C9' . . 120.3 no
D15C C15' D15D . . 107.7 no
D15C C15' N1' . . 109.4 no
D15D C15' N1' . . 109.7 no
D15C C15' C16' . . 109.5 no
D15D C15' C16' . . 109.5 no
N1' C15' C16' . . 111.0 no
C21' C16' C17' . . 120.2 no
C21' C16' C15' . . 120.5 no
C17' C16' C15' . . 119.2 no
D17' C17' C18' . . 119.7 no
D17' C17' C16' . . 120.2 no
C18' C17' C16' . . 120.1 no
D18' C18' C17' . . 120.2 no
D18' C18' C19' . . 120.1 no
C17' C18' C19' . . 119.7 no
D19' C19' C18' . . 119.7 no
D19' C19' C20' . . 120.1 no
C18' C19' C20' . . 120.2 no
D20' C20' C21' . . 119.7 no
D20' C20' C19' . . 120.1 no
C21' C20' C19' . . 120.1 no
D21' C21' C20' . . 120.1 no
D21' C21' C16' . . 120.2 no
C20' C21' C16' . . 119.7 no
C1 N1 C8 . . 124.5 no
C1 N1 C15 . . 116.7(5) no
C8 N1 C15 . . 118.5(5) no
N1 C1 C2 . . 114.1 no
N1 C1 S1 . . 126.7 no
C2 C1 S1 . . 119.0 no
C3 C2 C1 . . 119.6 no
C3 C2 C7 . . 121.2 no
C1 C2 C7 . . 116.0 no
C2 C3 C4 . . 121.8 no
C2 C3 H3 . . 117.3 no
C4 C3 H3 . . 118.5 no
C3 C4 C5 . . 112.8 no
C3 C4 H4A . . 109.0 no
C5 C4 H4A . . 109.0 no
C3 C4 H4B . . 109.0 no
C5 C4 H4B . . 109.0 no
H4A C4 H4B . . 107.8 no
C6 C5 C4 . . 110.8 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 . . 107.9 no
C5 C6 H6A . . 110.1 no
C7 C6 H6A . . 110.1 no
C5 C6 H6B . . 110.1 no
C7 C6 H6B . . 110.1 no
H6A C6 H6B . . 108.4 no
C2 C7 C6 . . 112.1 no
C2 C7 H7A . . 109.2 no
C6 C7 H7A . . 109.2 no
C2 C7 H7B . . 109.2 no
C6 C7 H7B . . 109.2 no
H7A C7 H7B . . 107.9 no
D8A C8 D8B . . 109.5(5) no
D8A C8 N1 . . 108.4(4) no
D8B C8 N1 . . 113.0(4) no
D8A C8 C9 . . 102.1(5) no
D8B C8 C9 . . 103.7(4) no
N1 C8 C9 . . 119.3(3) no
D14 C14 C9 . . 120.8(4) no
D14 C14 C13 . . 119.2(4) no
C9 C14 C13 . . 120.0 no
C14 C9 C10 . . 120.0 no
C14 C9 C8 . . 119.2(3) no
C10 C9 C8 . . 120.7(3) no
D10 C10 C11 . . 121.1(4) no
D10 C10 C9 . . 118.9(4) no
C11 C10 C9 . . 120.0 no
D11 C11 C10 . . 120.2(5) no
D11 C11 C12 . . 119.7(5) no
C10 C11 C12 . . 120.0 no
D12 C12 C13 . . 113.1(5) no
D12 C12 C11 . . 126.8(5) no
C13 C12 C11 . . 120.0 no
D13 C13 C12 . . 120.9(4) no
D13 C13 C14 . . 118.7(4) no
C12 C13 C14 . . 120.0 no
D15B C15 D15A . . 106.6(10) no
D15B C15 C16 . . 113.1(9) no
D15A C15 C16 . . 121.0(4) no
D15B C15 N1 . . 98.1(4) no
D15A C15 N1 . . 107.0(8) no
C16 C15 N1 . . 108.5(7) no
D21 C21 C16 . . 120.5 no
D21 C21 C20 . . 119.2 no
C16 C21 C20 . . 120.0 no
C21 C16 C17 . . 120.0 no
C21 C16 C15 . . 119.2(4) no
C17 C16 C15 . . 120.2(4) no
D17 C17 C18 . . 116.7 no
D17 C17 C16 . . 122.8 no
C18 C17 C16 . . 120.0 no
D18 C18 C17 . . 116.5 no
D18 C18 C19 . . 123.3 no
C17 C18 C19 . . 120.0 no
D19 C19 C20 . . 126.4 no
D19 C19 C18 . . 113.6 no
C20 C19 C18 . . 120.0 no
D20 C20 C19 . . 109.1 no
D20 C20 C21 . . 130.4 no
C19 C20 C21 . . 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' . 1.6237 no
N1' C1' . 1.3343 no
N1' C8' . 1.4519 no
N1' C15' . 1.4846 no
C1' C2' . 1.4912 no
C2' C8' . 1.5322 no
C2' C7' . 1.5476 no
C2' C3' . 1.5537 no
C3' D3' . 1.00(3) no
C3' C4' . 1.5117 no
C3' H3' . 1.04(4) no
C3' H3 . 1.2935 no
C4' C5' . 1.5375 no
C4' H4A' . 1.0920 no
C4' H4B' . 1.0920 no
C5' C6' . 1.4861 no
C5' H5A' . 1.0920 no
C5' H5B' . 1.0920 no
C6' C7' . 1.5506 no
C6' H6A' . 1.0920 no
C6' H6B' . 1.0920 no
C7' H7A' . 1.0920 no
C7' H7B' . 1.0920 no
C8' D8' . 0.9837 no
C8' C9' . 1.5088 no
C9' C10' . 1.3900 no
C9' C14' . 1.3982 no
C10' D10' . 1.0893 no
C10' C11' . 1.3961 no
C11' D11' . 1.0829 no
C11' C12' . 1.3982 no
C12' D12' . 1.0876 no
C12' C13' . 1.3903 no
C13' D13' . 1.0891 no
C13' C14' . 1.3955 no
C14' D14' . 1.0831 no
C15' D15C . 1.0932 no
C15' D15D . 1.0979 no
C15' C16' . 1.5338 no
C16' C21' . 1.3934 no
C16' C17' . 1.3990 no
C17' D17' . 1.0860 no
C17' C18' . 1.3925 no
C18' D18' . 1.0902 no
C18' C19' . 1.3939 no
C19' D19' . 1.0850 no
C19' C20' . 1.3993 no
C20' D20' . 1.0860 no
C20' C21' . 1.3931 no
C21' D21' . 1.0902 no
D3' H3 . 0.4856 no
S1 C1 . 1.7323 no
N1 C1 . 1.3460 no
N1 C8 . 1.3877 no
N1 C15 . 1.560(8) no
C1 C2 . 1.5183 no
C2 C3 . 1.3248 no
C2 C7 . 1.5269 no
C3 C4 . 1.5382 no
C3 H3 . 1.0765 no
C4 C5 . 1.5605 no
C4 H4A . 1.0920 no
C4 H4B . 1.0920 no
C5 C6 . 1.5199 no
C5 H5A . 1.0920 no
C5 H5B . 1.0920 no
C6 C7 . 1.5486 no
C6 H6A . 1.0920 no
C6 H6B . 1.0920 no
C7 H7A . 1.0920 no
C7 H7B . 1.0920 no
C8 D8A . 1.088(6) no
C8 D8B . 1.100(6) no
C8 C9 . 1.571(8) no
C14 D14 . 1.083(5) no
C14 C9 . 1.3900 no
C14 C13 . 1.3900 no
C9 C10 . 1.3900 no
C10 D10 . 1.089(5) no
C10 C11 . 1.3900 no
C11 D11 . 1.092(5) no
C11 C12 . 1.3900 no
C12 D12 . 1.092(5) no
C12 C13 . 1.3900 no
C13 D13 . 1.079(5) no
C15 D15B . 1.087(9) no
C15 D15A . 1.101(11) no
C15 C16 . 1.443(11) no
C21 D21 . 1.0873 no
C21 C16 . 1.3900 no
C21 C20 . 1.3900 no
C16 C17 . 1.3900 no
C17 D17 . 1.0884 no
C17 C18 . 1.3900 no
C18 D18 . 1.0964 no
C18 C19 . 1.3900 no
C19 D19 . 1.0856 no
C19 C20 . 1.3900 no
C20 D20 . 1.0254 no