#------------------------------------------------------------------------------
#$Date: 2022-10-07 04:08:56 +0300 (Fri, 07 Oct 2022) $
#$Revision: 278449 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/06/17/7061768.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_7061768
loop_
_publ_author_name
'Savateev, Konstantin V.'
'Fedotov, Victor V.'
'Slepukhin, Pavel A.'
'Ulomsky, Evgeniy N.'
'Rusinov, Vladimir L.'
_publ_section_title
;
 Regiospecific route to N9-alkylated thioxanthines
;
_journal_issue                   36
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              17145
_journal_page_last               17148
_journal_paper_doi               10.1039/D2NJ03002K
_journal_volume                  46
_journal_year                    2022
_chemical_formula_moiety         'C18 H22 N8 O2 S2, 2(C2 H6 O S)'
_chemical_formula_sum            'C22 H34 N8 O4 S4'
_chemical_formula_weight         602.81
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2022-04-01
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2022-04-01 deposited with the CCDC.	2022-08-25 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 103.129(7)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   13.4433(9)
_cell_length_b                   27.1914(16)
_cell_length_c                   16.9657(14)
_cell_measurement_reflns_used    3254
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      28.0590
_cell_measurement_theta_min      3.7940
_cell_volume                     6039.6(8)
_computing_cell_refinement       'CrysAlisPro 1.171.39.38a (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.38a (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.38a (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      295(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.5253
_diffrn_detector_type            Sapphire3
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.921
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -45.00  44.00   1.00   60.00    --  -23.92  57.00  90.00   89
  2  ω    -91.00  -3.00   1.00   60.00    --  -23.92 -77.00 120.00   88
  3  ω    -90.00   3.00   1.00   60.00    --  -23.92 -77.00-150.00   93
  4  ω    -51.00  40.00   1.00   60.00    --  -23.92  77.00 -30.00   91
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0162991000
_diffrn_orient_matrix_UB_12      0.0224696000
_diffrn_orient_matrix_UB_13      0.0141634000
_diffrn_orient_matrix_UB_21      -0.0516246000
_diffrn_orient_matrix_UB_22      -0.0065799000
_diffrn_orient_matrix_UB_23      -0.0163842000
_diffrn_orient_matrix_UB_31      -0.0022469000
_diffrn_orient_matrix_UB_32      -0.0114771000
_diffrn_orient_matrix_UB_33      0.0370977000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0559
_diffrn_reflns_av_unetI/netI     0.0819
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.921
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       38
_diffrn_reflns_limit_k_min       -34
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            23879
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.921
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.496
_diffrn_reflns_theta_min         3.749
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.356
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.86778
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.38a (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.326
_exptl_crystal_description       prism
_exptl_crystal_F_000             2544
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.27
_refine_diff_density_max         0.363
_refine_diff_density_min         -0.309
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.005
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     383
_refine_ls_number_reflns         8489
_refine_ls_number_restraints     42
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.1710
_refine_ls_R_factor_gt           0.0683
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1007P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1760
_refine_ls_wR_factor_ref         0.2487
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3428
_reflns_number_total             8489
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2nj03002k2.cif
_cod_data_source_block           exp_1044
_cod_depositor_comments
'Adding full bibliography for 7061766--7061768.cif.'
_cod_database_code               7061768
_shelx_shelxl_version_number     2018/3
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_max   0.910
_shelx_estimated_absorpt_t_min   0.862
_reflns_odcompleteness_completeness 99.62
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     28.22
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All C(H,H,H,H,H,H) groups
2. Restrained distances
 C3-C12
 1.54 with sigma of 0.02
 C12-C13
 1.54 with sigma of 0.02
 C12-C11
 1.54 with sigma of 0.02
 C14-C00W
 1.54 with sigma of 0.02
 C14-C5
 1.54 with sigma of 0.02
 C14-C7
 1.54 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C7) \\sim Ueq, Uanis(C5) \\sim Ueq, Uanis(C3) \\sim Ueq: with sigma of
0.01 and sigma for terminal atoms of 0.02
Uanis(C2S) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(S3) \\sim Ueq, Uanis(C1) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
4. Others
 Fixed Sof: S1S(0.8) H14A(0.5) H14B(0.5) H14C(0.5) H14D(0.5) H1SD(0.2)
 H1SE(0.2) H1SF(0.2) H1SA(0.8) H1SB(0.8) H1SC(0.8) C13(0.8) H13A(0.8) H13B(0.8)
 H13C(0.8) H12A(0.8) H12B(0.8) H12C(0.2) H12D(0.2) C2S(0.8) H2SA(0.8) H2SB(0.8)
 H2SC(0.8) C3(0.2) H3A(0.2) H3B(0.2) H3C(0.2) C7(0.5) H7A(0.5) H7B(0.5)
 H7C(0.5) C5(0.5) H5A(0.5) H5B(0.5) H5C(0.5) C1(0.2) H1A(0.2) H1B(0.2) H1C(0.2)
 S3(0.2)
5.a Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C00S(H00A,H00B), C11(H11A,H11B), C00W(H00C,H00D), C14(H14A,
 H14B), C14(H14C,H14D), C12(H12A,H12B), C12(H12C,H12D)
5.b Me refined with riding coordinates:
 C4S(H4SA,H4SB,H4SC), C13(H13A,H13B,H13C), C3(H3A,H3B,H3C), C7(H7A,H7B,H7C),
 C5(H5A,H5B,H5C)
5.c Aromatic/amide H refined with riding coordinates:
 N16(H16), N3(H3), C6(H6), C19(H19)
5.d Idealised Me refined as rotating group:
 C3S(H3SA,H3SB,H3SC), C1S(H1SD,H1SE,H1SF), C1S(H1SA,H1SB,H1SC), C2S(H2SA,H2SB,
 H2SC), C1(H1A,H1B,H1C)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.092
_oxdiff_exptl_absorpt_empirical_full_min 0.926
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.77604(7) 0.70842(4) 0.86245(6) 0.0715(3) Uani 1 1 d . . . . .
S2 S 0.77577(7) 0.63467(4) 0.85230(6) 0.0744(3) Uani 1 1 d . . . . .
S2S S 0.76958(9) 0.88200(4) 0.90065(8) 0.0932(4) Uani 1 1 d . . . . .
S1S S 0.78609(12) 0.47644(6) 0.88789(11) 0.0878(4) Uani 0.8 1 d . . P A 1
N1 N 0.6243(2) 0.69248(10) 0.73151(17) 0.0626(7) Uani 1 1 d . . . . .
O2S O 0.7962(2) 0.83025(9) 0.88522(19) 0.0912(9) Uani 1 1 d . . . . .
N14 N 0.8630(2) 0.66225(10) 0.73166(18) 0.0645(7) Uani 1 1 d . . . . .
N16 N 0.8341(2) 0.57779(10) 0.74612(18) 0.0663(7) Uani 1 1 d . . . . .
H16 H 0.810937 0.556393 0.774714 0.080 Uiso 1 1 calc R U . . .
N3 N 0.6733(2) 0.77427(10) 0.76234(18) 0.0643(7) Uani 1 1 d . . . . .
H3 H 0.712327 0.792998 0.796957 0.077 Uiso 1 1 calc R U . . .
N7 N 0.4941(2) 0.68740(11) 0.60800(18) 0.0673(8) Uani 1 1 d . . . . .
O1 O 0.6094(2) 0.84173(10) 0.6863(2) 0.0979(9) Uani 1 1 d . . . . .
O2 O 0.8694(3) 0.51626(10) 0.66493(19) 0.1040(10) Uani 1 1 d . . . . .
N5 N 0.4753(2) 0.76678(12) 0.57366(19) 0.0729(8) Uani 1 1 d . . . . .
N20 N 0.9311(2) 0.67707(11) 0.61385(19) 0.0738(8) Uani 1 1 d . . . . .
N18 N 0.9414(3) 0.60035(14) 0.5692(2) 0.0854(9) Uani 1 1 d . . . . .
C21 C 0.8969(2) 0.64727(13) 0.6659(2) 0.0621(8) Uani 1 1 d . . . . .
C2 C 0.6797(2) 0.72576(12) 0.7764(2) 0.0593(8) Uani 1 1 d . . . . .
O1S O 0.7420(2) 0.51229(12) 0.8255(2) 0.1134(11) Uani 1 1 d . . . . .
C8 C 0.5602(2) 0.71296(13) 0.6664(2) 0.0607(8) Uani 1 1 d . . . . .
C15 C 0.8321(2) 0.62523(13) 0.7681(2) 0.0619(8) Uani 1 1 d . . . . .
C22 C 0.9033(3) 0.60016(14) 0.6377(2) 0.0672(9) Uani 1 1 d . . . . .
C9 C 0.5477(3) 0.76121(13) 0.6447(2) 0.0626(8) Uani 1 1 d . . . . .
C4 C 0.6076(3) 0.79743(14) 0.6952(2) 0.0685(9) Uani 1 1 d . . . . .
C17 C 0.8713(3) 0.56029(14) 0.6798(2) 0.0733(10) Uani 1 1 d . . . . .
C6 C 0.4450(3) 0.72189(16) 0.5538(2) 0.0748(10) Uani 1 1 d . . . . .
H6 H 0.395281 0.714100 0.507767 0.090 Uiso 1 1 calc R U . . .
C19 C 0.9556(3) 0.64707(18) 0.5575(3) 0.0865(12) Uani 1 1 d . . . . .
H19 H 0.980512 0.658724 0.514206 0.104 Uiso 1 1 calc R U . . .
C10 C 0.4775(3) 0.63480(15) 0.6064(3) 0.0853(12) Uani 1 1 d . . . . .
H10A H 0.416785 0.627307 0.564972 0.102 Uiso 1 1 calc R U . . .
H10B H 0.464997 0.624621 0.658031 0.102 Uiso 1 1 calc R U . . .
C00S C 0.9451(4) 0.73067(16) 0.6213(3) 0.0945(14) Uani 1 1 d . . . . .
H00A H 0.981542 0.738422 0.676084 0.113 Uiso 1 1 calc R U . . .
H00B H 0.986944 0.741413 0.584909 0.113 Uiso 1 1 calc R U . . .
C4S C 0.6357(4) 0.88655(19) 0.8786(4) 0.1224(18) Uani 1 1 d . . . . .
H4SA H 0.616409 0.919639 0.888101 0.184 Uiso 1 1 calc R U . . .
H4SB H 0.608646 0.878061 0.822972 0.184 Uiso 1 1 calc R U . . .
H4SC H 0.608989 0.864440 0.912820 0.184 Uiso 1 1 calc R U . . .
C11 C 0.5639(5) 0.6060(2) 0.5902(4) 0.136(2) Uani 1 1 d D . . . .
H11A H 0.624376 0.613754 0.631655 0.164 Uiso 1 1 calc R U . . .
H11B H 0.576477 0.616633 0.538711 0.164 Uiso 1 1 calc R U . . .
C3S C 0.7896(5) 0.91546(18) 0.8168(4) 0.137(2) Uani 1 1 d . . . . .
H3SA H 0.860624 0.914179 0.815653 0.205 Uiso 1 1 calc R U . . .
H3SB H 0.769614 0.949068 0.821162 0.205 Uiso 1 1 calc R U . . .
H3SC H 0.749521 0.901401 0.767936 0.205 Uiso 1 1 calc R U . . .
C00W C 0.8505(5) 0.7574(2) 0.6032(5) 0.151(2) Uani 1 1 d D . . . .
H00C H 0.811656 0.748586 0.642809 0.181 Uiso 1 1 calc R U . . .
H00D H 0.811420 0.746951 0.550589 0.181 Uiso 1 1 calc R U . . .
C14 C 0.8609(9) 0.8119(3) 0.6026(7) 0.219(5) Uani 1 1 d D . . . .
H14A H 0.889475 0.819392 0.556392 0.262 Uiso 0.5 1 calc R U P B 1
H14B H 0.791695 0.824616 0.589730 0.262 Uiso 0.5 1 calc R U P B 1
H14C H 0.886186 0.819726 0.659371 0.262 Uiso 0.5 1 calc R U P C 2
H14D H 0.918708 0.816737 0.578120 0.262 Uiso 0.5 1 calc R U P C 2
C1S C 0.9105(4) 0.4629(2) 0.8815(4) 0.132(2) Uani 1 1 d . . . . .
H1SD H 0.874077 0.449161 0.831078 0.199 Uiso 0.2 1 calc R U P A 2
H1SE H 0.938526 0.436797 0.917992 0.199 Uiso 0.2 1 calc R U P A 2
H1SF H 0.964831 0.483418 0.872297 0.199 Uiso 0.2 1 calc R U P A 2
H1SA H 0.911019 0.432744 0.852165 0.199 Uiso 0.8 1 calc R U P A 1
H1SB H 0.952772 0.459364 0.935044 0.199 Uiso 0.8 1 calc R U P A 1
H1SC H 0.936399 0.489060 0.853909 0.199 Uiso 0.8 1 calc R U P A 1
C13 C 0.5157(10) 0.5257(4) 0.6492(10) 0.270(8) Uani 0.8 1 d D . P D 1
H13A H 0.511349 0.491174 0.637309 0.405 Uiso 0.8 1 calc R U P D 1
H13B H 0.563067 0.531047 0.700112 0.405 Uiso 0.8 1 calc R U P D 1
H13C H 0.449590 0.537815 0.652252 0.405 Uiso 0.8 1 calc R U P D 1
C12 C 0.5497(8) 0.5509(3) 0.5876(7) 0.210(4) Uani 1 1 d D . . . .
H12A H 0.502068 0.543249 0.536966 0.252 Uiso 0.8 1 calc R U P D 1
H12B H 0.614762 0.536528 0.584496 0.252 Uiso 0.8 1 calc R U P D 1
H12C H 0.482605 0.542138 0.555753 0.252 Uiso 0.2 1 calc R U P D 2
H12D H 0.557593 0.537649 0.641721 0.252 Uiso 0.2 1 calc R U P D 2
C2S C 0.8221(8) 0.5145(3) 0.9747(5) 0.150(4) Uani 0.8 1 d . U P A 1
H2SA H 0.873201 0.537423 0.966908 0.226 Uiso 0.8 1 calc R U P A 1
H2SB H 0.849079 0.494429 1.021248 0.226 Uiso 0.8 1 calc R U P A 1
H2SC H 0.763366 0.532070 0.982932 0.226 Uiso 0.8 1 calc R U P A 1
C3 C 0.634(3) 0.531(2) 0.548(3) 0.28(3) Uani 0.2 1 d D U P D 2
H3A H 0.629780 0.496209 0.543948 0.422 Uiso 0.2 1 calc R U P D 2
H3B H 0.625208 0.545157 0.494431 0.422 Uiso 0.2 1 calc R U P D 2
H3C H 0.699700 0.540698 0.579830 0.422 Uiso 0.2 1 calc R U P D 2
C7 C 0.9143(15) 0.8409(7) 0.6656(12) 0.216(9) Uani 0.5 1 d D U P E 1
H7A H 0.908853 0.874773 0.649484 0.325 Uiso 0.5 1 calc R U P E 1
H7B H 0.886034 0.836555 0.712281 0.325 Uiso 0.5 1 calc R U P E 1
H7C H 0.984863 0.831276 0.678586 0.325 Uiso 0.5 1 calc R U P E 1
C5 C 0.7996(16) 0.8507(8) 0.5745(15) 0.260(10) Uani 0.5 1 d D U P E 2
H5A H 0.837506 0.880677 0.587113 0.390 Uiso 0.5 1 calc R U P E 2
H5B H 0.775491 0.847886 0.516908 0.390 Uiso 0.5 1 calc R U P E 2
H5C H 0.742387 0.850930 0.599616 0.390 Uiso 0.5 1 calc R U P E 2
C1 C 0.7413(18) 0.4550(10) 0.9459(18) 0.132(9) Uani 0.2 1 d . U P A 2
H1A H 0.730074 0.433332 0.900035 0.198 Uiso 0.2 1 calc R U P A 2
H1B H 0.676803 0.466992 0.953200 0.198 Uiso 0.2 1 calc R U P A 2
H1C H 0.775320 0.437394 0.993482 0.198 Uiso 0.2 1 calc R U P A 2
S3 S 0.8148(8) 0.5031(3) 0.9300(6) 0.112(3) Uani 0.2 1 d . U P A 2
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 S1 S2 101.94(12) . . ?
C15 S2 S1 102.67(12) . . ?
O2S S2S C4S 107.7(2) . . ?
O2S S2S C3S 105.0(2) . . ?
C4S S2S C3S 97.4(3) . . ?
O1S S1S C1S 109.5(2) . . ?
O1S S1S C2S 101.6(3) . . ?
C1S S1S C2S 95.2(4) . . ?
C2 N1 C8 111.4(3) . . ?
C15 N14 C21 111.2(3) . . ?
C15 N16 H16 117.4 . . ?
C15 N16 C17 125.2(3) . . ?
C17 N16 H16 117.4 . . ?
C2 N3 H3 117.2 . . ?
C2 N3 C4 125.7(3) . . ?
C4 N3 H3 117.2 . . ?
C8 N7 C6 105.9(3) . . ?
C8 N7 C10 126.2(3) . . ?
C6 N7 C10 127.9(3) . . ?
C6 N5 C9 103.9(3) . . ?
C21 N20 C00S 126.3(3) . . ?
C19 N20 C21 105.8(3) . . ?
C19 N20 C00S 127.7(3) . . ?
C19 N18 C22 103.1(3) . . ?
N14 C21 C22 128.5(3) . . ?
N20 C21 N14 125.6(3) . . ?
N20 C21 C22 105.9(3) . . ?
N1 C2 S1 120.5(3) . . ?
N1 C2 N3 125.1(3) . . ?
N3 C2 S1 114.4(3) . . ?
N1 C8 N7 124.9(3) . . ?
N1 C8 C9 129.2(3) . . ?
N7 C8 C9 106.0(3) . . ?
N14 C15 S2 120.7(3) . . ?
N14 C15 N16 125.7(3) . . ?
N16 C15 S2 113.5(2) . . ?
N18 C22 C21 110.8(3) . . ?
N18 C22 C17 130.0(4) . . ?
C21 C22 C17 119.2(3) . . ?
N5 C9 C4 129.9(3) . . ?
C8 C9 N5 111.2(3) . . ?
C8 C9 C4 118.9(3) . . ?
N3 C4 C9 109.8(3) . . ?
O1 C4 N3 120.9(3) . . ?
O1 C4 C9 129.2(4) . . ?
N16 C17 C22 110.2(3) . . ?
O2 C17 N16 119.9(4) . . ?
O2 C17 C22 129.8(4) . . ?
N7 C6 H6 123.5 . . ?
N5 C6 N7 113.0(4) . . ?
N5 C6 H6 123.5 . . ?
N20 C19 H19 122.8 . . ?
N18 C19 N20 114.4(3) . . ?
N18 C19 H19 122.8 . . ?
N7 C10 H10A 108.8 . . ?
N7 C10 H10B 108.8 . . ?
N7 C10 C11 113.8(4) . . ?
H10A C10 H10B 107.7 . . ?
C11 C10 H10A 108.8 . . ?
C11 C10 H10B 108.8 . . ?
N20 C00S H00A 108.9 . . ?
N20 C00S H00B 108.9 . . ?
H00A C00S H00B 107.8 . . ?
C00W C00S N20 113.2(4) . . ?
C00W C00S H00A 108.9 . . ?
C00W C00S H00B 108.9 . . ?
S2S C4S H4SA 109.5 . . ?
S2S C4S H4SB 109.5 . . ?
S2S C4S H4SC 109.5 . . ?
H4SA C4S H4SB 109.5 . . ?
H4SA C4S H4SC 109.5 . . ?
H4SB C4S H4SC 109.5 . . ?
C10 C11 H11A 108.4 . . ?
C10 C11 H11B 108.4 . . ?
C10 C11 C12 115.6(5) . . ?
H11A C11 H11B 107.4 . . ?
C12 C11 H11A 108.4 . . ?
C12 C11 H11B 108.4 . . ?
S2S C3S H3SA 109.5 . . ?
S2S C3S H3SB 109.5 . . ?
S2S C3S H3SC 109.5 . . ?
H3SA C3S H3SB 109.5 . . ?
H3SA C3S H3SC 109.5 . . ?
H3SB C3S H3SC 109.5 . . ?
C00S C00W H00C 108.5 . . ?
C00S C00W H00D 108.5 . . ?
C00S C00W C14 115.2(6) . . ?
H00C C00W H00D 107.5 . . ?
C14 C00W H00C 108.5 . . ?
C14 C00W H00D 108.5 . . ?
C00W C14 H14A 105.7 . . ?
C00W C14 H14B 105.7 . . ?
C00W C14 H14C 103.0 . . ?
C00W C14 H14D 103.0 . . ?
H14A C14 H14B 106.2 . . ?
H14C C14 H14D 105.1 . . ?
C7 C14 C00W 126.3(13) . . ?
C7 C14 H14A 105.7 . . ?
C7 C14 H14B 105.7 . . ?
C5 C14 C00W 136.6(16) . . ?
C5 C14 H14C 103.0 . . ?
C5 C14 H14D 103.0 . . ?
S1S C1S H1SA 109.5 . . ?
S1S C1S H1SB 109.5 . . ?
S1S C1S H1SC 109.5 . . ?
H1SD C1S H1SE 109.5 . . ?
H1SD C1S H1SF 109.5 . . ?
H1SE C1S H1SF 109.5 . . ?
H1SA C1S H1SB 109.5 . . ?
H1SA C1S H1SC 109.5 . . ?
H1SB C1S H1SC 109.5 . . ?
S3 C1S H1SD 109.5 . . ?
S3 C1S H1SE 109.5 . . ?
S3 C1S H1SF 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
C11 C12 H12A 107.0 . . ?
C11 C12 H12B 107.0 . . ?
C11 C12 H12C 110.8 . . ?
C11 C12 H12D 110.8 . . ?
C11 C12 C3 105(2) . . ?
C13 C12 C11 121.3(9) . . ?
C13 C12 H12A 107.0 . . ?
C13 C12 H12B 107.0 . . ?
H12A C12 H12B 106.7 . . ?
H12C C12 H12D 108.9 . . ?
C3 C12 H12C 110.8 . . ?
C3 C12 H12D 110.8 . . ?
S1S C2S H2SA 109.5 . . ?
S1S C2S H2SB 109.5 . . ?
S1S C2S H2SC 109.5 . . ?
H2SA C2S H2SB 109.5 . . ?
H2SA C2S H2SC 109.5 . . ?
H2SB C2S H2SC 109.5 . . ?
C12 C3 H3A 109.5 . . ?
C12 C3 H3B 109.5 . . ?
C12 C3 H3C 109.5 . . ?
H3A C3 H3B 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C14 C7 H7A 109.5 . . ?
C14 C7 H7B 109.5 . . ?
C14 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C14 C5 H5A 109.5 . . ?
C14 C5 H5B 109.5 . . ?
C14 C5 H5C 109.5 . . ?
H5A C5 H5B 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
S3 C1 H1A 109.5 . . ?
S3 C1 H1B 109.5 . . ?
S3 C1 H1C 109.5 . . ?
O1S S3 C1S 85.9(4) . . ?
C1 S3 O1S 93.2(10) . . ?
C1 S3 C1S 95.5(12) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 S2 2.0129(15) . ?
S1 C2 1.781(4) . ?
S2 C15 1.781(3) . ?
S2S O2S 1.490(3) . ?
S2S C4S 1.757(5) . ?
S2S C3S 1.760(6) . ?
S1S O1S 1.462(3) . ?
S1S C1S 1.740(5) . ?
S1S C2S 1.774(9) . ?
N1 C2 1.303(4) . ?
N1 C8 1.357(4) . ?
N14 C21 1.360(4) . ?
N14 C15 1.298(4) . ?
N16 H16 0.8600 . ?
N16 C15 1.345(4) . ?
N16 C17 1.414(5) . ?
N3 H3 0.8600 . ?
N3 C2 1.340(4) . ?
N3 C4 1.420(4) . ?
N7 C8 1.361(4) . ?
N7 C6 1.373(5) . ?
N7 C10 1.447(5) . ?
O1 C4 1.215(4) . ?
O2 C17 1.223(4) . ?
N5 C9 1.375(5) . ?
N5 C6 1.306(5) . ?
N20 C21 1.354(4) . ?
N20 C19 1.352(5) . ?
N20 C00S 1.471(5) . ?
N18 C22 1.373(5) . ?
N18 C19 1.307(5) . ?
C21 C22 1.376(5) . ?
O1S S3 1.838(10) . ?
C8 C9 1.363(5) . ?
C22 C17 1.417(5) . ?
C9 C4 1.429(5) . ?
C6 H6 0.9300 . ?
C19 H19 0.9300 . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 C11 1.476(6) . ?
C00S H00A 0.9700 . ?
C00S H00B 0.9700 . ?
C00S C00W 1.436(7) . ?
C4S H4SA 0.9600 . ?
C4S H4SB 0.9600 . ?
C4S H4SC 0.9600 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 C12 1.510(8) . ?
C3S H3SA 0.9600 . ?
C3S H3SB 0.9600 . ?
C3S H3SC 0.9600 . ?
C00W H00C 0.9700 . ?
C00W H00D 0.9700 . ?
C00W C14 1.487(8) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 H14C 0.9700 . ?
C14 H14D 0.9700 . ?
C14 C7 1.390(14) . ?
C14 C5 1.357(15) . ?
C1S H1SD 0.9600 . ?
C1S H1SE 0.9600 . ?
C1S H1SF 0.9600 . ?
C1S H1SA 0.9600 . ?
C1S H1SB 0.9600 . ?
C1S H1SC 0.9600 . ?
C1S S3 2.002(11) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C13 C12 1.410(12) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 H12C 0.9700 . ?
C12 H12D 0.9700 . ?
C12 C3 1.540(19) . ?
C2S H2SA 0.9600 . ?
C2S H2SB 0.9600 . ?
C2S H2SC 0.9600 . ?
C3 H3A 0.9600 . ?
C3 H3B 0.9600 . ?
C3 H3C 0.9600 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C1 S3 1.70(2) . ?
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
S1 S2 C15 N14 1.4(3) . . . . ?
S1 S2 C15 N16 -175.9(2) . . . . ?
S2 S1 C2 N1 6.5(3) . . . . ?
S2 S1 C2 N3 -171.5(2) . . . . ?
N1 C8 C9 N5 179.4(3) . . . . ?
N1 C8 C9 C4 -0.5(5) . . . . ?
N14 C21 C22 N18 179.8(3) . . . . ?
N14 C21 C22 C17 0.3(6) . . . . ?
N7 C8 C9 N5 -0.2(4) . . . . ?
N7 C8 C9 C4 179.9(3) . . . . ?
N7 C10 C11 C12 -179.8(6) . . . . ?
N5 C9 C4 N3 -179.5(3) . . . . ?
N5 C9 C4 O1 -1.2(6) . . . . ?
N20 C21 C22 N18 0.2(4) . . . . ?
N20 C21 C22 C17 -179.3(3) . . . . ?
N20 C00S C00W C14 -174.7(6) . . . . ?
N18 C22 C17 N16 -178.0(4) . . . . ?
N18 C22 C17 O2 -0.4(7) . . . . ?
C21 N14 C15 S2 -175.8(2) . . . . ?
C21 N14 C15 N16 1.2(5) . . . . ?
C21 N20 C19 N18 -0.8(5) . . . . ?
C21 N20 C00S C00W -73.8(6) . . . . ?
C21 C22 C17 N16 1.5(5) . . . . ?
C21 C22 C17 O2 179.1(4) . . . . ?
C2 N1 C8 N7 179.0(3) . . . . ?
C2 N1 C8 C9 -0.6(5) . . . . ?
C2 N3 C4 O1 -177.7(3) . . . . ?
C2 N3 C4 C9 0.7(4) . . . . ?
C8 N1 C2 S1 -176.1(2) . . . . ?
C8 N1 C2 N3 1.8(4) . . . . ?
C8 N7 C6 N5 0.1(4) . . . . ?
C8 N7 C10 C11 -70.8(5) . . . . ?
C8 C9 C4 N3 0.4(4) . . . . ?
C8 C9 C4 O1 178.7(4) . . . . ?
C15 N14 C21 N20 177.9(3) . . . . ?
C15 N14 C21 C22 -1.7(5) . . . . ?
C15 N16 C17 O2 -179.8(3) . . . . ?
C15 N16 C17 C22 -1.9(5) . . . . ?
C22 N18 C19 N20 0.9(5) . . . . ?
C9 N5 C6 N7 -0.3(4) . . . . ?
C4 N3 C2 S1 175.9(2) . . . . ?
C4 N3 C2 N1 -2.0(5) . . . . ?
C17 N16 C15 S2 177.8(3) . . . . ?
C17 N16 C15 N14 0.6(5) . . . . ?
C6 N7 C8 N1 -179.6(3) . . . . ?
C6 N7 C8 C9 0.0(3) . . . . ?
C6 N7 C10 C11 111.8(5) . . . . ?
C6 N5 C9 C8 0.3(4) . . . . ?
C6 N5 C9 C4 -179.9(3) . . . . ?
C19 N20 C21 N14 -179.3(4) . . . . ?
C19 N20 C21 C22 0.3(4) . . . . ?
C19 N20 C00S C00W 110.9(5) . . . . ?
C19 N18 C22 C21 -0.6(4) . . . . ?
C19 N18 C22 C17 178.8(4) . . . . ?
C10 N7 C8 N1 2.6(5) . . . . ?
C10 N7 C8 C9 -177.8(3) . . . . ?
C10 N7 C6 N5 177.9(3) . . . . ?
C10 C11 C12 C13 -48.9(13) . . . . ?
C10 C11 C12 C3 165(2) . . . . ?
C00S N20 C21 N14 4.6(6) . . . . ?
C00S N20 C21 C22 -175.8(4) . . . . ?
C00S N20 C19 N18 175.3(4) . . . . ?
C00S C00W C14 C7 -56.1(17) . . . . ?
C00S C00W C14 C5 163.8(18) . . . . ?
