#------------------------------------------------------------------------------
#$Date: 2025-07-06 19:40:44 +0200 (Sun 06 de Jul de 2025) $
#$Revision: 301077 $
#$URL: svn://www.crystallography.net/cod/cif/7/06/38/7063804.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_7063804
loop_
_publ_author_name
'Aminov, Semen V.'
'Fedotov, Victor V.'
'Savateev, Konstantin V.'
'Neymash, Artyom O.'
'Ulomsky, Evgeny N.'
'Slepukhin, Pavel A.'
'Rusinov, Vladimir L.'
_publ_section_title
;
 ANRORC-type reactions of azolo[1,5-a]pyrimidine-6-carbonitriles with O-
 and N-nucleophiles
;
_journal_issue                   21
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              8627
_journal_page_last               8631
_journal_paper_doi               10.1039/D5NJ00255A
_journal_volume                  49
_journal_year                    2025
_chemical_formula_moiety         'C18 H16 N6 O S'
_chemical_formula_sum            'C18 H16 N6 O S'
_chemical_formula_weight         364.43
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2024-10-17
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2024-10-21 deposited with the CCDC.	2025-05-07 downloaded from the CCDC.
;
_cell_angle_alpha                91.963(3)
_cell_angle_beta                 96.868(3)
_cell_angle_gamma                93.117(4)
_cell_formula_units_Z            4
_cell_length_a                   6.7798(3)
_cell_length_b                   10.5381(5)
_cell_length_c                   24.4272(10)
_cell_measurement_reflns_used    4784
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      29.9130
_cell_measurement_theta_min      2.5230
_cell_volume                     1728.68(13)
_computing_cell_refinement       'CrysAlisPro 1.171.41.98a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.98a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.98a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (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_area_resol_mean 15.9555
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.852
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     -4.00  31.00   1.00   15.00    --   23.14  77.00  60.00   35
  2  ω    -40.00  38.00   1.00   15.00    --   23.14 -57.00  60.00   78
  3  ω     -1.00  28.00   1.00   15.00    --   23.14  77.00-180.00   29
  4  ω     -4.00  30.00   1.00   15.00    --   23.14  77.00 -60.00   34
  5  ω    -39.00  36.00   1.00   15.00    --   23.14 -57.00 -60.00   75
  6  ω    -39.00  38.00   1.00   15.00    --   23.14 -57.00-180.00   77
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur 3'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0151
_diffrn_reflns_av_unetI/netI     0.0413
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.852
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            13003
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.852
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.759
_diffrn_reflns_theta_min         2.512
_exptl_absorpt_coefficient_mu    0.208
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.97490
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.98a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.400
_exptl_crystal_description       prism
_exptl_crystal_F_000             760
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.39
_exptl_crystal_size_min          0.31
_refine_diff_density_max         0.376
_refine_diff_density_min         -0.410
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     493
_refine_ls_number_reflns         9203
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.0903
_refine_ls_R_factor_gt           0.0553
_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)+(0.1000P)²+0.1000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1523
_refine_ls_wR_factor_ref         0.1848
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6020
_reflns_number_total             9203
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d5nj00255a2.cif
_cod_data_source_block           exp_1349
_cod_depositor_comments
'Adding full bibliography for 7063804--7063806.cif.'
_cod_database_code               7063804
_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   0.938
_shelx_estimated_absorpt_t_min   0.907
_olex2_refinement_description
;
1. Restrained distances
 C18-C19
 1.4 with sigma of 0.02
 C4-C20
 1.4 with sigma of 0.02
 C17-C4
 1.4 with sigma of 0.02
 S3-C19
 1.65 with sigma of 0.02
 S3-C17
 1.65 with sigma of 0.02
 C18-C17
 1.4 with sigma of 0.02
2. Uiso/Uaniso restraints and constraints
Uanis(C4) = Uanis(C18)
3. Others
 Fixed Sof: S1(0.8) C18(0.8) H18(0.8) H19(0.8) H19A(0.2) H20(0.8) H20A(0.2)
 S3(0.2) C4(0.2) H4(0.2)
4.a Aromatic/amide H refined with riding coordinates:
 C7(H7), C12(H12), C13(H13), C15(H15), C16(H16), C18(H18), C19(H19), C19(H19A),
  C20(H20), C20(H20A), C7A(H7A), C12A(H12A), C13A(H13A), C15A(H15A), C16A(H16A),
  C18A(H18A), C19A(H19B), C20A(H20B), C4(H4)
4.b X=CH2 refined with riding coordinates:
 N5A(H5AA,H5AB)
4.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C2(H2A,H2B,H2C), C1A(H1AA,H1AB,H1AC), C2A(H2AA,H2AB,H2AC)
;
_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
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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
C1 C 1.2733(5) 0.7676(3) -0.03270(11) 0.0786(9) Uani 1 1 d . . . . .
H1A H 1.311991 0.834559 -0.055591 0.118 Uiso 1 1 calc R U . . .
H1B H 1.164325 0.792941 -0.013915 0.118 Uiso 1 1 calc R U . . .
H1C H 1.232923 0.692040 -0.055223 0.118 Uiso 1 1 calc R U . . .
N1 N 1.0630(2) 0.21084(14) 0.25286(7) 0.0362(4) Uani 1 1 d . . . . .
N5 N 1.3406(3) 0.12335(18) 0.22682(8) 0.0462(4) Uani 1 1 d . . . . .
S1 S 0.84581(14) -0.05745(9) 0.36678(5) 0.0503(2) Uani 0.8 1 d . . P A 1
C2 C 1.6278(5) 0.8066(3) 0.00230(13) 0.0793(9) Uani 1 1 d . . . . .
H2A H 1.719146 0.745767 -0.007594 0.119 Uiso 1 1 calc R U . . .
H2B H 1.679132 0.848832 0.036927 0.119 Uiso 1 1 calc R U . . .
H2C H 1.611338 0.868145 -0.025718 0.119 Uiso 1 1 calc R U . . .
N2 N 1.0164(3) 0.11296(15) 0.28545(7) 0.0395(4) Uani 1 1 d . . . . .
O2 O 1.5316(3) 0.26940(16) 0.15917(7) 0.0586(4) Uani 1 1 d . . . . .
C3 C 0.8558(3) 0.15496(18) 0.30488(8) 0.0371(4) Uani 1 1 d . . . . .
N3 N 1.4390(3) 0.7424(2) 0.00722(9) 0.0635(6) Uani 1 1 d . . . . .
N4 N 0.7977(3) 0.27045(16) 0.28840(7) 0.0422(4) Uani 1 1 d . . . . .
C5 C 0.9308(3) 0.30409(18) 0.25536(8) 0.0383(4) Uani 1 1 d . . . . .
N6 N 0.9493(3) 0.41337(16) 0.22872(8) 0.0455(4) Uani 1 1 d . . . . .
C7 C 1.0977(3) 0.42037(19) 0.19868(9) 0.0426(5) Uani 1 1 d . . . . .
H7 H 1.113855 0.494878 0.179960 0.051 Uiso 1 1 calc R U . . .
C8 C 1.2346(3) 0.32742(18) 0.19184(8) 0.0393(4) Uani 1 1 d . . . . .
C9 C 1.2214(3) 0.21722(18) 0.22329(8) 0.0370(4) Uani 1 1 d . . . . .
C10 C 1.3950(3) 0.3427(2) 0.15673(8) 0.0425(5) Uani 1 1 d . . . . .
C11 C 1.3973(3) 0.4485(2) 0.11786(8) 0.0413(4) Uani 1 1 d . . . . .
C12 C 1.2317(3) 0.4813(2) 0.08337(9) 0.0473(5) Uani 1 1 d . . . . .
H12 H 1.109005 0.439224 0.085666 0.057 Uiso 1 1 calc R U . . .
C13 C 1.2455(4) 0.5751(2) 0.04575(9) 0.0497(5) Uani 1 1 d . . . . .
H13 H 1.132924 0.592813 0.022247 0.060 Uiso 1 1 calc R U . . .
C14 C 1.4249(3) 0.6438(2) 0.04228(9) 0.0470(5) Uani 1 1 d . . . . .
C15 C 1.5913(4) 0.6108(2) 0.07735(10) 0.0526(6) Uani 1 1 d . . . . .
H15 H 1.713230 0.654917 0.076225 0.063 Uiso 1 1 calc R U . . .
C16 C 1.5778(3) 0.5138(2) 0.11358(9) 0.0490(5) Uani 1 1 d . . . . .
H16 H 1.691636 0.491942 0.135512 0.059 Uiso 1 1 calc R U . . .
C17 C 0.7539(3) 0.08109(19) 0.34337(8) 0.0405(4) Uani 1 1 d D . . . .
C18 C 0.5930(13) 0.1114(8) 0.3689(4) 0.0622(18) Uani 0.8 1 d D . P A 1
H18 H 0.524045 0.184184 0.361959 0.075 Uiso 0.8 1 calc R U P A 1
C19 C 0.5418(4) 0.0201(3) 0.40741(12) 0.0681(7) Uani 1 1 d D . . . .
H19 H 0.435171 0.024296 0.427949 0.082 Uiso 0.8 1 calc R U P A 1
H19A H 0.441307 0.015688 0.430192 0.082 Uiso 0.2 1 calc R U P A 2
C20 C 0.6699(4) -0.0729(2) 0.40966(11) 0.0619(7) Uani 1 1 d D . . . .
H20 H 0.662102 -0.140425 0.433013 0.074 Uiso 0.8 1 calc R U P A 1
H20A H 0.677943 -0.142344 0.432166 0.074 Uiso 0.2 1 calc R U P A 2
C1A C -0.3389(4) 0.6260(3) 0.51913(11) 0.0657(7) Uani 1 1 d . . . . .
H1AA H -0.300675 0.542956 0.529462 0.099 Uiso 1 1 calc R U . . .
H1AB H -0.432554 0.618626 0.486279 0.099 Uiso 1 1 calc R U . . .
H1AC H -0.399117 0.665582 0.548464 0.099 Uiso 1 1 calc R U . . .
N1A N 0.6060(2) 0.72944(15) 0.24722(7) 0.0376(4) Uani 1 1 d . . . . .
N5A N 0.6181(3) 0.52200(16) 0.27191(8) 0.0484(5) Uani 1 1 d . . . . .
H5AA H 0.717759 0.515627 0.253451 0.058 Uiso 1 1 calc R U . . .
H5AB H 0.575168 0.457522 0.288640 0.058 Uiso 1 1 calc R U . . .
S1A S 1.08792(10) 0.79374(7) 0.14289(3) 0.0637(2) Uani 1 1 d . . . . .
C2A C -0.0811(5) 0.7948(3) 0.55089(12) 0.0795(9) Uani 1 1 d . . . . .
H2AA H -0.087930 0.878363 0.536567 0.119 Uiso 1 1 calc R U . . .
H2AB H 0.055362 0.778085 0.561957 0.119 Uiso 1 1 calc R U . . .
H2AC H -0.154048 0.789837 0.582175 0.119 Uiso 1 1 calc R U . . .
N2A N 0.7657(3) 0.72814(16) 0.21774(7) 0.0416(4) Uani 1 1 d . . . . .
O2A O 0.3095(3) 0.44704(14) 0.32936(7) 0.0574(4) Uani 1 1 d . . . . .
C3A C 0.7668(3) 0.84443(19) 0.19827(8) 0.0392(4) Uani 1 1 d . . . . .
N3A N -0.1660(3) 0.7022(2) 0.50895(8) 0.0537(5) Uani 1 1 d . . . . .
N4A N 0.6233(3) 0.91991(16) 0.21261(7) 0.0426(4) Uani 1 1 d . . . . .
C5A C 0.5229(3) 0.84568(18) 0.24364(8) 0.0392(4) Uani 1 1 d . . . . .
N6A N 0.3618(3) 0.87231(16) 0.26840(7) 0.0460(4) Uani 1 1 d . . . . .
C7A C 0.2921(3) 0.7791(2) 0.29659(9) 0.0455(5) Uani 1 1 d . . . . .
H7A H 0.181394 0.794943 0.314330 0.055 Uiso 1 1 calc R U . . .
C8A C 0.3683(3) 0.65783(19) 0.30255(8) 0.0405(4) Uani 1 1 d . . . . .
C9A C 0.5317(3) 0.63021(18) 0.27455(8) 0.0379(4) Uani 1 1 d . . . . .
C10A C 0.2798(3) 0.5606(2) 0.33575(9) 0.0430(5) Uani 1 1 d . . . . .
C11A C 0.1569(3) 0.60268(19) 0.37889(8) 0.0410(4) Uani 1 1 d . . . . .
C12A C -0.0137(3) 0.5314(2) 0.38773(9) 0.0469(5) Uani 1 1 d . . . . .
H12A H -0.055785 0.460318 0.364850 0.056 Uiso 1 1 calc R U . . .
C13A C -0.1221(3) 0.5642(2) 0.42992(9) 0.0484(5) Uani 1 1 d . . . . .
H13A H -0.238389 0.516529 0.434167 0.058 Uiso 1 1 calc R U . . .
C14A C -0.0603(3) 0.6681(2) 0.46648(8) 0.0415(4) Uani 1 1 d . . . . .
C15A C 0.1128(3) 0.7391(2) 0.45717(9) 0.0457(5) Uani 1 1 d . . . . .
H15A H 0.158591 0.808657 0.480558 0.055 Uiso 1 1 calc R U . . .
C16A C 0.2156(3) 0.7072(2) 0.41403(9) 0.0448(5) Uani 1 1 d . . . . .
H16A H 0.327842 0.757323 0.408265 0.054 Uiso 1 1 calc R U . . .
C17A C 0.9098(3) 0.8879(2) 0.16242(8) 0.0431(5) Uani 1 1 d . . . . .
C18A C 0.9137(4) 1.0082(2) 0.13807(9) 0.0493(5) Uani 1 1 d . . . . .
H18A H 0.826449 1.071744 0.142637 0.059 Uiso 1 1 calc R U . . .
C19A C 1.0756(4) 1.0148(3) 0.10511(11) 0.0675(7) Uani 1 1 d . . . . .
H19B H 1.107479 1.086355 0.085962 0.081 Uiso 1 1 calc R U . . .
C20A C 1.1776(4) 0.9082(3) 0.10428(11) 0.0687(7) Uani 1 1 d . . . . .
H20B H 1.285522 0.898988 0.084581 0.082 Uiso 1 1 calc R U . . .
H5A H 1.314(4) 0.052(3) 0.2432(10) 0.056(7) Uiso 1 1 d . . . . .
H5B H 1.437(4) 0.130(2) 0.2058(10) 0.059(7) Uiso 1 1 d . . . . .
S3 S 0.5511(14) 0.1384(8) 0.3679(4) 0.0561(14) Uani 0.2 1 d D . P A 2
C4 C 0.792(3) -0.0357(17) 0.3674(8) 0.0622(18) Uani 0.2 1 d D . P A 2
H4 H 0.890649 -0.086180 0.356895 0.075 Uiso 0.2 1 calc R 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
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
N3 C1 H1A 109.5 . . ?
N3 C1 H1B 109.5 . . ?
N3 C1 H1C 109.5 . . ?
C5 N1 N2 110.31(15) . . ?
C9 N1 N2 125.26(15) . . ?
C9 N1 C5 124.40(16) . . ?
C9 N5 H5A 123.0(17) . . ?
C9 N5 H5B 114.3(17) . . ?
H5A N5 H5B 122(2) . . ?
C20 S1 C17 91.27(12) . . ?
H2A C2 H2B 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
N3 C2 H2A 109.5 . . ?
N3 C2 H2B 109.5 . . ?
N3 C2 H2C 109.5 . . ?
C3 N2 N1 100.70(15) . . ?
N2 C3 N4 116.79(17) . . ?
N2 C3 C17 120.62(17) . . ?
N4 C3 C17 122.56(17) . . ?
C2 N3 C1 117.8(2) . . ?
C14 N3 C1 120.4(2) . . ?
C14 N3 C2 120.8(2) . . ?
C5 N4 C3 102.62(15) . . ?
N4 C5 N1 109.58(16) . . ?
N4 C5 N6 128.44(17) . . ?
N6 C5 N1 121.92(17) . . ?
C7 N6 C5 114.82(17) . . ?
N6 C7 H7 116.5 . . ?
N6 C7 C8 127.01(18) . . ?
C8 C7 H7 116.5 . . ?
C7 C8 C9 117.22(17) . . ?
C7 C8 C10 123.35(18) . . ?
C9 C8 C10 119.33(17) . . ?
N1 C9 C8 114.35(16) . . ?
N5 C9 N1 117.61(17) . . ?
N5 C9 C8 128.04(18) . . ?
O2 C10 C8 120.99(18) . . ?
O2 C10 C11 118.62(18) . . ?
C8 C10 C11 120.39(18) . . ?
C12 C11 C10 123.94(19) . . ?
C12 C11 C16 117.79(19) . . ?
C16 C11 C10 118.18(19) . . ?
C11 C12 H12 119.3 . . ?
C13 C12 C11 121.3(2) . . ?
C13 C12 H12 119.3 . . ?
C12 C13 H13 119.4 . . ?
C12 C13 C14 121.3(2) . . ?
C14 C13 H13 119.4 . . ?
N3 C14 C13 122.1(2) . . ?
N3 C14 C15 120.7(2) . . ?
C13 C14 C15 117.1(2) . . ?
C14 C15 H15 119.4 . . ?
C16 C15 C14 121.2(2) . . ?
C16 C15 H15 119.4 . . ?
C11 C16 H16 119.4 . . ?
C15 C16 C11 121.2(2) . . ?
C15 C16 H16 119.4 . . ?
C3 C17 S1 120.33(15) . . ?
C3 C17 S3 119.3(3) . . ?
C18 C17 S1 110.9(3) . . ?
C18 C17 C3 128.5(3) . . ?
C4 C17 C3 132.1(6) . . ?
C4 C17 S3 108.6(7) . . ?
C17 C18 H18 123.4 . . ?
C17 C18 C19 113.1(4) . . ?
C19 C18 H18 123.4 . . ?
C18 C19 H19 124.9 . . ?
C20 C19 C18 110.1(3) . . ?
C20 C19 H19 124.9 . . ?
C20 C19 H19A 117.9 . . ?
C20 C19 S3 124.2(3) . . ?
S3 C19 H19A 117.9 . . ?
S1 C20 H20 122.7 . . ?
C19 C20 S1 114.6(2) . . ?
C19 C20 H20 122.7 . . ?
C19 C20 H20A 129.5 . . ?
C19 C20 C4 101.0(6) . . ?
C4 C20 H20A 129.5 . . ?
H1AA C1A H1AB 109.5 . . ?
H1AA C1A H1AC 109.5 . . ?
H1AB C1A H1AC 109.5 . . ?
N3A C1A H1AA 109.5 . . ?
N3A C1A H1AB 109.5 . . ?
N3A C1A H1AC 109.5 . . ?
N2A N1A C5A 109.92(15) . . ?
C9A N1A N2A 126.23(15) . . ?
C9A N1A C5A 123.79(16) . . ?
H5AA N5A H5AB 120.0 . . ?
C9A N5A H5AA 120.0 . . ?
C9A N5A H5AB 120.0 . . ?
C20A S1A C17A 91.97(13) . . ?
H2AA C2A H2AB 109.5 . . ?
H2AA C2A H2AC 109.5 . . ?
H2AB C2A H2AC 109.5 . . ?
N3A C2A H2AA 109.5 . . ?
N3A C2A H2AB 109.5 . . ?
N3A C2A H2AC 109.5 . . ?
C3A N2A N1A 101.20(15) . . ?
N2A C3A N4A 116.54(18) . . ?
N2A C3A C17A 122.01(18) . . ?
N4A C3A C17A 121.44(18) . . ?
C1A N3A C2A 118.1(2) . . ?
C14A N3A C1A 120.1(2) . . ?
C14A N3A C2A 120.2(2) . . ?
C5A N4A C3A 102.79(16) . . ?
N4A C5A N1A 109.55(16) . . ?
N4A C5A N6A 128.14(17) . . ?
N6A C5A N1A 122.30(17) . . ?
C7A N6A C5A 114.78(17) . . ?
N6A C7A H7A 116.7 . . ?
N6A C7A C8A 126.55(18) . . ?
C8A C7A H7A 116.7 . . ?
C7A C8A C10A 122.12(18) . . ?
C9A C8A C7A 117.75(18) . . ?
C9A C8A C10A 120.12(17) . . ?
N1A C9A C8A 114.69(16) . . ?
N5A C9A N1A 117.54(17) . . ?
N5A C9A C8A 127.77(18) . . ?
O2A C10A C8A 121.46(18) . . ?
O2A C10A C11A 119.96(18) . . ?
C8A C10A C11A 118.56(17) . . ?
C12A C11A C10A 120.33(19) . . ?
C16A C11A C10A 121.72(19) . . ?
C16A C11A C12A 117.77(19) . . ?
C11A C12A H12A 119.4 . . ?
C13A C12A C11A 121.1(2) . . ?
C13A C12A H12A 119.4 . . ?
C12A C13A H13A 119.4 . . ?
C12A C13A C14A 121.3(2) . . ?
C14A C13A H13A 119.4 . . ?
N3A C14A C13A 122.14(19) . . ?
N3A C14A C15A 120.85(19) . . ?
C13A C14A C15A 116.99(18) . . ?
C14A C15A H15A 119.5 . . ?
C16A C15A C14A 121.0(2) . . ?
C16A C15A H15A 119.5 . . ?
C11A C16A H16A 119.1 . . ?
C15A C16A C11A 121.9(2) . . ?
C15A C16A H16A 119.1 . . ?
C3A C17A S1A 122.18(16) . . ?
C18A C17A S1A 112.77(16) . . ?
C18A C17A C3A 125.0(2) . . ?
C17A C18A H18A 125.9 . . ?
C17A C18A C19A 108.2(2) . . ?
C19A C18A H18A 125.9 . . ?
C18A C19A H19B 122.8 . . ?
C20A C19A C18A 114.3(2) . . ?
C20A C19A H19B 122.8 . . ?
S1A C20A H20B 123.7 . . ?
C19A C20A S1A 112.67(19) . . ?
C19A C20A H20B 123.7 . . ?
C19 S3 C17 89.8(3) . . ?
C17 C4 C20 116.2(11) . . ?
C17 C4 H4 121.9 . . ?
C20 C4 H4 121.9 . . ?
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
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C1 N3 1.440(4) . ?
N1 N2 1.371(2) . ?
N1 C5 1.370(2) . ?
N1 C9 1.364(2) . ?
N5 C9 1.310(2) . ?
N5 H5A 0.88(3) . ?
N5 H5B 0.88(3) . ?
S1 C17 1.708(2) . ?
S1 C20 1.684(3) . ?
C2 H2A 0.9600 . ?
C2 H2B 0.9600 . ?
C2 H2C 0.9600 . ?
C2 N3 1.434(4) . ?
N2 C3 1.330(2) . ?
O2 C10 1.235(2) . ?
C3 N4 1.359(2) . ?
C3 C17 1.454(3) . ?
N3 C14 1.375(3) . ?
N4 C5 1.323(2) . ?
C5 N6 1.349(2) . ?
N6 C7 1.315(3) . ?
C7 H7 0.9300 . ?
C7 C8 1.405(3) . ?
C8 C9 1.419(3) . ?
C8 C10 1.469(3) . ?
C10 C11 1.490(3) . ?
C11 C12 1.387(3) . ?
C11 C16 1.388(3) . ?
C12 H12 0.9300 . ?
C12 C13 1.379(3) . ?
C13 H13 0.9300 . ?
C13 C14 1.395(3) . ?
C14 C15 1.400(3) . ?
C15 H15 0.9300 . ?
C15 C16 1.381(3) . ?
C16 H16 0.9300 . ?
C17 C18 1.367(7) . ?
C17 S3 1.696(7) . ?
C17 C4 1.405(14) . ?
C18 H18 0.9300 . ?
C18 C19 1.426(8) . ?
C19 H19 0.9300 . ?
C19 H19A 0.9300 . ?
C19 C20 1.343(4) . ?
C19 S3 1.606(8) . ?
C20 H20 0.9300 . ?
C20 H20A 0.9300 . ?
C20 C4 1.450(14) . ?
C1A H1AA 0.9600 . ?
C1A H1AB 0.9600 . ?
C1A H1AC 0.9600 . ?
C1A N3A 1.436(3) . ?
N1A N2A 1.371(2) . ?
N1A C5A 1.377(2) . ?
N1A C9A 1.365(2) . ?
N5A H5AA 0.8600 . ?
N5A H5AB 0.8600 . ?
N5A C9A 1.313(2) . ?
S1A C17A 1.705(2) . ?
S1A C20A 1.688(3) . ?
C2A H2AA 0.9600 . ?
C2A H2AB 0.9600 . ?
C2A H2AC 0.9600 . ?
C2A N3A 1.436(3) . ?
N2A C3A 1.330(2) . ?
O2A C10A 1.232(2) . ?
C3A N4A 1.360(3) . ?
C3A C17A 1.449(3) . ?
N3A C14A 1.378(3) . ?
N4A C5A 1.325(2) . ?
C5A N6A 1.348(2) . ?
N6A C7A 1.317(3) . ?
C7A H7A 0.9300 . ?
C7A C8A 1.410(3) . ?
C8A C9A 1.408(3) . ?
C8A C10A 1.474(3) . ?
C10A C11A 1.490(3) . ?
C11A C12A 1.387(3) . ?
C11A C16A 1.384(3) . ?
C12A H12A 0.9300 . ?
C12A C13A 1.381(3) . ?
C13A H13A 0.9300 . ?
C13A C14A 1.402(3) . ?
C14A C15A 1.402(3) . ?
C15A H15A 0.9300 . ?
C15A C16A 1.373(3) . ?
C16A H16A 0.9300 . ?
C17A C18A 1.418(3) . ?
C18A H18A 0.9300 . ?
C18A C19A 1.437(3) . ?
C19A H19B 0.9300 . ?
C19A C20A 1.351(4) . ?
C20A H20B 0.9300 . ?
C4 H4 0.9300 . ?
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
C1 N3 C14 C13 -8.3(4) . . . . ?
C1 N3 C14 C15 173.6(2) . . . . ?
N1 N2 C3 N4 -0.8(2) . . . . ?
N1 N2 C3 C17 -178.80(18) . . . . ?
N1 C5 N6 C7 2.8(3) . . . . ?
S1 C17 C18 C19 -0.9(9) . . . . ?
C2 N3 C14 C13 -176.4(2) . . . . ?
C2 N3 C14 C15 5.4(4) . . . . ?
N2 N1 C5 N4 -0.3(2) . . . . ?
N2 N1 C5 N6 177.13(19) . . . . ?
N2 N1 C9 N5 -1.1(3) . . . . ?
N2 N1 C9 C8 178.71(18) . . . . ?
N2 C3 N4 C5 0.7(2) . . . . ?
N2 C3 C17 S1 3.1(3) . . . . ?
N2 C3 C17 C18 177.3(6) . . . . ?
N2 C3 C17 S3 179.3(5) . . . . ?
N2 C3 C17 C4 0.9(14) . . . . ?
O2 C10 C11 C12 135.2(2) . . . . ?
O2 C10 C11 C16 -41.2(3) . . . . ?
C3 N4 C5 N1 -0.2(2) . . . . ?
C3 N4 C5 N6 -177.4(2) . . . . ?
C3 C17 C18 C19 -175.5(4) . . . . ?
C3 C17 S3 C19 -175.5(3) . . . . ?
C3 C17 C4 C20 172.8(7) . . . . ?
N3 C14 C15 C16 178.5(2) . . . . ?
N4 C3 C17 S1 -174.75(17) . . . . ?
N4 C3 C17 C18 -0.6(7) . . . . ?
N4 C3 C17 S3 1.5(6) . . . . ?
N4 C3 C17 C4 -177.0(14) . . . . ?
N4 C5 N6 C7 179.7(2) . . . . ?
C5 N1 N2 C3 0.6(2) . . . . ?
C5 N1 C9 N5 176.9(2) . . . . ?
C5 N1 C9 C8 -3.3(3) . . . . ?
C5 N6 C7 C8 0.1(3) . . . . ?
N6 C7 C8 C9 -4.6(4) . . . . ?
N6 C7 C8 C10 179.2(2) . . . . ?
C7 C8 C9 N1 5.7(3) . . . . ?
C7 C8 C9 N5 -174.6(2) . . . . ?
C7 C8 C10 O2 167.4(2) . . . . ?
C7 C8 C10 C11 -11.8(3) . . . . ?
C8 C10 C11 C12 -45.6(3) . . . . ?
C8 C10 C11 C16 138.0(2) . . . . ?
C9 N1 N2 C3 178.86(19) . . . . ?
C9 N1 C5 N4 -178.52(19) . . . . ?
C9 N1 C5 N6 -1.1(3) . . . . ?
C9 C8 C10 O2 -8.8(3) . . . . ?
C9 C8 C10 C11 172.03(19) . . . . ?
C10 C8 C9 N1 -177.85(18) . . . . ?
C10 C8 C9 N5 1.9(3) . . . . ?
C10 C11 C12 C13 -175.9(2) . . . . ?
C10 C11 C16 C15 178.4(2) . . . . ?
C11 C12 C13 C14 -2.4(3) . . . . ?
C12 C11 C16 C15 1.8(3) . . . . ?
C12 C13 C14 N3 -176.3(2) . . . . ?
C12 C13 C14 C15 2.0(3) . . . . ?
C13 C14 C15 C16 0.3(3) . . . . ?
C14 C15 C16 C11 -2.2(4) . . . . ?
C16 C11 C12 C13 0.4(3) . . . . ?
C17 S1 C20 C19 0.7(3) . . . . ?
C17 C3 N4 C5 178.61(19) . . . . ?
C17 C18 C19 C20 1.4(9) . . . . ?
C18 C19 C20 S1 -1.3(6) . . . . ?
C19 C20 C4 C17 5.2(18) . . . . ?
C20 S1 C17 C3 175.30(19) . . . . ?
C20 S1 C17 C18 0.2(5) . . . . ?
C20 C19 S3 C17 -0.3(8) . . . . ?
C1A N3A C14A C13A 3.9(3) . . . . ?
C1A N3A C14A C15A -177.8(2) . . . . ?
N1A N2A C3A N4A 0.1(2) . . . . ?
N1A N2A C3A C17A -178.28(19) . . . . ?
N1A C5A N6A C7A 0.7(3) . . . . ?
S1A C17A C18A C19A -2.0(3) . . . . ?
C2A N3A C14A C13A 169.4(3) . . . . ?
C2A N3A C14A C15A -12.4(3) . . . . ?
N2A N1A C5A N4A 0.2(2) . . . . ?
N2A N1A C5A N6A 179.26(19) . . . . ?
N2A N1A C9A N5A -1.2(3) . . . . ?
N2A N1A C9A C8A 178.83(19) . . . . ?
N2A C3A N4A C5A 0.0(3) . . . . ?
N2A C3A C17A S1A -0.4(3) . . . . ?
N2A C3A C17A C18A 176.8(2) . . . . ?
O2A C10A C11A C12A -40.3(3) . . . . ?
O2A C10A C11A C16A 134.6(2) . . . . ?
C3A N4A C5A N1A -0.1(2) . . . . ?
C3A N4A C5A N6A -179.1(2) . . . . ?
C3A C17A C18A C19A -179.5(2) . . . . ?
N3A C14A C15A C16A -178.3(2) . . . . ?
N4A C3A C17A S1A -178.72(16) . . . . ?
N4A C3A C17A C18A -1.5(3) . . . . ?
N4A C5A N6A C7A 179.5(2) . . . . ?
C5A N1A N2A C3A -0.2(2) . . . . ?
C5A N1A C9A N5A 175.9(2) . . . . ?
C5A N1A C9A C8A -4.1(3) . . . . ?
C5A N6A C7A C8A -0.4(4) . . . . ?
N6A C7A C8A C9A -2.1(4) . . . . ?
N6A C7A C8A C10A 179.2(2) . . . . ?
C7A C8A C9A N1A 4.1(3) . . . . ?
C7A C8A C9A N5A -175.9(2) . . . . ?
C7A C8A C10A O2A 160.3(2) . . . . ?
C7A C8A C10A C11A -21.5(3) . . . . ?
C8A C10A C11A C12A 141.4(2) . . . . ?
C8A C10A C11A C16A -43.6(3) . . . . ?
C9A N1A N2A C3A 177.26(19) . . . . ?
C9A N1A C5A N4A -177.33(18) . . . . ?
C9A N1A C5A N6A 1.7(3) . . . . ?
C9A C8A C10A O2A -18.3(3) . . . . ?
C9A C8A C10A C11A 159.9(2) . . . . ?
C10A C8A C9A N1A -177.24(19) . . . . ?
C10A C8A C9A N5A 2.8(4) . . . . ?
C10A C11A C12A C13A 175.6(2) . . . . ?
C10A C11A C16A C15A -173.6(2) . . . . ?
C11A C12A C13A C14A -2.2(4) . . . . ?
C12A C11A C16A C15A 1.5(3) . . . . ?
C12A C13A C14A N3A -179.8(2) . . . . ?
C12A C13A C14A C15A 1.9(3) . . . . ?
C13A C14A C15A C16A 0.0(3) . . . . ?
C14A C15A C16A C11A -1.7(3) . . . . ?
C16A C11A C12A C13A 0.5(3) . . . . ?
C17A S1A C20A C19A -0.8(2) . . . . ?
C17A C3A N4A C5A 178.4(2) . . . . ?
C17A C18A C19A C20A 1.4(3) . . . . ?
C18A C19A C20A S1A -0.3(3) . . . . ?
C20A S1A C17A C3A 179.2(2) . . . . ?
C20A S1A C17A C18A 1.7(2) . . . . ?
S3 C17 C4 C20 -6(2) . . . . ?
S3 C19 C20 C4 -2.7(11) . . . . ?
C4 C17 S3 C19 3.3(14) . . . . ?
