#------------------------------------------------------------------------------
#$Date: 2025-07-06 19:40:44 +0200 (Sun 06 de Jul de 2025) $
#$Revision: 301077 $
#$URL: svn://www.crystallography.net/cod/cif/7/06/38/7063806.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_7063806
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 H23 N7'
_chemical_formula_sum            'C18 H23 N7'
_chemical_formula_weight         337.43
_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                99.885(4)
_cell_angle_beta                 93.772(4)
_cell_angle_gamma                106.915(4)
_cell_formula_units_Z            4
_cell_length_a                   9.5201(5)
_cell_length_b                   12.7114(6)
_cell_length_c                   16.2360(8)
_cell_measurement_reflns_used    3614
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      29.5970
_cell_measurement_theta_min      2.3830
_cell_volume                     1837.86(17)
_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 0.993
_diffrn_measured_fraction_theta_max 0.843
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -46.00  44.00   1.00   20.00    --   23.14 -57.00  90.00   90
  2  ω      7.00  92.00   1.00   20.00    --   23.14  57.00   0.00   85
  3  ω     -7.00  38.00   1.00   20.00    --   23.14  77.00  90.00   45
  4  ω     -7.00  20.00   1.00   20.00    --   23.14  77.00 -30.00   27
  5  ω      2.00  92.00   1.00   20.00    --   23.14  57.00-120.00   90
;
_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  0.0264
_diffrn_reflns_av_unetI/netI     0.0589
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.843
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            14416
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.843
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.862
_diffrn_reflns_theta_min         2.253
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.81871
_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    1.220
_exptl_crystal_description       prism
_exptl_crystal_F_000             720
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.29
_refine_diff_density_max         0.336
_refine_diff_density_min         -0.217
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     516
_refine_ls_number_reflns         9768
_refine_ls_number_restraints     18
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.1412
_refine_ls_R_factor_gt           0.0694
_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          0.1711
_refine_ls_wR_factor_ref         0.2261
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4889
_reflns_number_total             9768
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d5nj00255a2.cif
_cod_data_source_block           exp_1376
_cod_depositor_comments
'Adding full bibliography for 7063804--7063806.cif.'
_cod_original_cell_volume        1837.86(16)
_cod_database_code               7063806
_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   0.978
_shelx_estimated_absorpt_t_min   0.965
_olex2_refinement_description
;
1. Restrained distances
 C19B-C18B
 1.54 with sigma of 0.02
 C19A-C20A
 1.54 with sigma of 0.02
 C18A-C19A
 1.54 with sigma of 0.02
 C19B-C20A
 1.54 with sigma of 0.02
 C18A-C17A
 1.54 with sigma of 0.02
 C17A-C18B
 1.54 with sigma of 0.02
2. Uiso/Uaniso restraints and constraints
Uanis(C17C) \\sim Ueq, Uanis(C17) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
3. Others
 Fixed Sof: H18E(0.5) H18F(0.5) H18G(0.5) H18H(0.5) H17A(0.6) H17B(0.6)
 H17C(0.4) H17D(0.4) C17(0.5) H17E(0.5) H17F(0.5) C18A(0.6) H18A(0.6) H18B(0.6)
 C19A(0.6) H19A(0.6) H19B(0.6) H20A(0.6) H20B(0.6) H20C(0.6) H20D(0.4)
 H20E(0.4) H20F(0.4) C18B(0.4) H18C(0.4) H18D(0.4) C19B(0.4) H19C(0.4)
 H19D(0.4) C17C(0.5) H17G(0.5) H17H(0.5)
4.a Secondary CH2 refined with riding coordinates:
 C18(H18E,H18F), C18(H18G,H18H), C19(H19E,H19F), C17A(H17A,H17B), C17A(H17C,
 H17D), C17(H17E,H17F), C18A(H18A,H18B), C19A(H19A,H19B), C18B(H18C,H18D),
 C19B(H19C,H19D), C17C(H17G,H17H)
4.b Aromatic/amide H refined with riding coordinates:
 C13(H13), C12(H12), C15(H15), C16(H16), C15A(H15A), C16A(H16A), C13A(H13A),
 C12A(H12A)
4.c Idealised Me refined as rotating group:
 C2(H2A,H2B,H2C), C2A(H2AA,H2AB,H2AC), C1(H1A,H1B,H1C), C20(H20G,H20H,H20I),
 C1A(H1AA,H1AB,H1AC), C20A(H20A,H20B,H20C), C20A(H20D,H20E,H20F)
;
_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
N1A N 0.14028(19) 0.03132(14) 0.72635(10) 0.0456(4) Uani 1 1 d . . . . .
N1 N 0.2268(2) 0.56042(15) 0.76618(11) 0.0490(4) Uani 1 1 d . . . . .
N2A N 0.1174(2) -0.06143(15) 0.66309(11) 0.0558(5) Uani 1 1 d . . . . .
N2 N 0.2289(2) 0.50149(17) 0.82985(12) 0.0580(5) Uani 1 1 d . . . . .
N6 N 0.2160(3) 0.41319(17) 0.65728(15) 0.0656(6) Uani 1 1 d . . . . .
N5 N 0.2346(2) 0.74414(16) 0.75045(12) 0.0628(6) Uani 1 1 d . . . . .
N4 N 0.2428(2) 0.68330(18) 0.88286(12) 0.0634(5) Uani 1 1 d . . . . .
N4A N 0.1160(2) 0.09343(17) 0.60928(12) 0.0629(6) Uani 1 1 d . . . . .
N6A N 0.1648(3) -0.05926(17) 0.83588(14) 0.0669(6) Uani 1 1 d . . . . .
N5A N 0.1554(2) 0.22383(15) 0.74161(12) 0.0579(5) Uani 1 1 d . . . . .
N7A N 0.3004(3) 0.58413(19) 1.16662(15) 0.0797(7) Uani 1 1 d . . . . .
N7 N 0.3697(3) 0.93174(19) 0.36111(15) 0.0736(7) Uani 1 1 d . . . . .
C8A C 0.1602(2) 0.03305(17) 0.81104(13) 0.0466(5) Uani 1 1 d . . . . .
C8 C 0.2232(2) 0.51899(18) 0.68172(14) 0.0495(5) Uani 1 1 d . . . . .
C7A C 0.1741(3) 0.13738(17) 0.86343(13) 0.0491(5) Uani 1 1 d . . . . .
C9 C 0.2351(3) 0.66938(19) 0.79941(14) 0.0523(5) Uani 1 1 d . . . . .
C9A C 0.1388(2) 0.12324(18) 0.69309(14) 0.0496(5) Uani 1 1 d . . . . .
C7 C 0.2310(3) 0.59864(18) 0.62993(14) 0.0520(5) Uani 1 1 d . . . . .
C14 C 0.3388(3) 0.84436(19) 0.40460(14) 0.0531(6) Uani 1 1 d . . . . .
N3A N 0.1920(3) 0.06672(19) 0.98864(12) 0.0813(7) Uani 1 1 d . . . . .
C14A C 0.2742(3) 0.4807(2) 1.11327(14) 0.0560(6) Uani 1 1 d . . . . .
C6A C 0.1710(3) 0.22642(19) 0.82426(15) 0.0535(6) Uani 1 1 d . . . . .
C13 C 0.1936(3) 0.7902(2) 0.41763(15) 0.0566(6) Uani 1 1 d . . . . .
H13 H 0.116657 0.813512 0.396934 0.068 Uiso 1 1 calc R U . . .
C11A C 0.2207(3) 0.26816(19) 1.00715(14) 0.0550(6) Uani 1 1 d . . . . .
C11 C 0.2728(3) 0.66472(19) 0.49199(14) 0.0560(6) Uani 1 1 d . . . . .
N3 N 0.2282(3) 0.46879(19) 0.50556(14) 0.0928(9) Uani 1 1 d . . . . .
C12 C 0.1628(3) 0.7032(2) 0.46051(15) 0.0587(6) Uani 1 1 d . . . . .
H12 H 0.065317 0.669474 0.468509 0.070 Uiso 1 1 calc R U . . .
C15 C 0.4504(3) 0.8053(2) 0.43606(16) 0.0623(6) Uani 1 1 d . . . . .
H15 H 0.548071 0.838778 0.428387 0.075 Uiso 1 1 calc R U . . .
C10A C 0.1951(3) 0.1533(2) 0.95615(14) 0.0590(6) Uani 1 1 d . . . . .
C3A C 0.1037(3) -0.0173(2) 0.59605(15) 0.0613(6) Uani 1 1 d . . . . .
C6 C 0.2338(3) 0.7061(2) 0.66877(16) 0.0589(6) Uani 1 1 d . . . . .
C10 C 0.2406(3) 0.5705(2) 0.53917(15) 0.0612(6) Uani 1 1 d . . . . .
C3 C 0.2386(3) 0.5805(2) 0.89633(16) 0.0622(7) Uani 1 1 d . . . . .
C16 C 0.4167(3) 0.7174(2) 0.47840(16) 0.0650(7) Uani 1 1 d . . . . .
H16 H 0.492780 0.692693 0.498447 0.078 Uiso 1 1 calc R U . . .
C15A C 0.3887(3) 0.4450(2) 1.08384(17) 0.0677(7) Uani 1 1 d . . . . .
H15A H 0.485589 0.491485 1.099306 0.081 Uiso 1 1 calc R U . . .
C16A C 0.3615(3) 0.3410(2) 1.03156(17) 0.0693(7) Uani 1 1 d . . . . .
H16A H 0.441047 0.319732 1.012379 0.083 Uiso 1 1 calc R U . . .
C13A C 0.1323(3) 0.4082(2) 1.08693(17) 0.0711(7) Uani 1 1 d . . . . .
H13A H 0.052025 0.429763 1.104599 0.085 Uiso 1 1 calc R U . . .
C12A C 0.1071(3) 0.3047(2) 1.03517(17) 0.0722(7) Uani 1 1 d . . . . .
H12A H 0.010218 0.258515 1.018819 0.087 Uiso 1 1 calc R U . . .
C2 C 0.5218(3) 0.9901(2) 0.35369(19) 0.0829(9) Uani 1 1 d . . . . .
H2A H 0.573068 1.027775 0.408566 0.124 Uiso 1 1 calc R U . . .
H2B H 0.524632 1.044166 0.318681 0.124 Uiso 1 1 calc R U . . .
H2C H 0.568778 0.937095 0.328886 0.124 Uiso 1 1 calc R U . . .
C18 C 0.1978(4) 0.3199(2) 0.38335(18) 0.0830(9) Uani 1 1 d . . . . .
H18E H 0.100863 0.273076 0.390894 0.100 Uiso 0.5 1 calc R U P A 1
H18F H 0.270315 0.303069 0.419408 0.100 Uiso 0.5 1 calc R U P A 1
H18G H 0.230560 0.273317 0.416926 0.100 Uiso 0.5 1 calc R U P B 2
H18H H 0.092914 0.307298 0.386363 0.100 Uiso 0.5 1 calc R U P B 2
C19 C 0.2236(4) 0.2874(3) 0.29215(18) 0.0857(9) Uani 1 1 d . . . . .
H19E H 0.172208 0.208089 0.271913 0.103 Uiso 1 1 calc R U . . .
H19F H 0.180630 0.328638 0.258228 0.103 Uiso 1 1 calc R U . . .
C2A C 0.4436(4) 0.6414(3) 1.2117(2) 0.0997(11) Uani 1 1 d . . . . .
H2AA H 0.471943 0.593948 1.245319 0.149 Uiso 1 1 calc R U . . .
H2AB H 0.441490 0.709110 1.247680 0.149 Uiso 1 1 calc R U . . .
H2AC H 0.513860 0.659593 1.172563 0.149 Uiso 1 1 calc R U . . .
C17A C 0.2133(5) 0.0786(3) 1.08078(17) 0.1065(13) Uani 1 1 d D . . . .
H17A H 0.124305 0.034362 1.099507 0.128 Uiso 0.6 1 calc R U P C 1
H17B H 0.232740 0.156505 1.107726 0.128 Uiso 0.6 1 calc R U P C 1
H17C H 0.301243 0.140685 1.104361 0.128 Uiso 0.4 1 calc R U P D 2
H17D H 0.129227 0.094954 1.104448 0.128 Uiso 0.4 1 calc R U P D 2
C1 C 0.2622(4) 0.9878(3) 0.3478(2) 0.1073(13) Uani 1 1 d . . . . .
H1A H 0.179221 0.937435 0.309766 0.161 Uiso 1 1 calc R U . . .
H1B H 0.305708 1.052243 0.324180 0.161 Uiso 1 1 calc R U . . .
H1C H 0.229628 1.011283 0.400641 0.161 Uiso 1 1 calc R U . . .
C20 C 0.3815(4) 0.3091(3) 0.2796(2) 0.1119(12) Uani 1 1 d . . . . .
H20G H 0.388828 0.281251 0.221720 0.168 Uiso 1 1 calc R U . . .
H20H H 0.426554 0.271732 0.315074 0.168 Uiso 1 1 calc R U . . .
H20I H 0.431366 0.388367 0.293814 0.168 Uiso 1 1 calc R U . . .
C1A C 0.1780(4) 0.6143(3) 1.2007(3) 0.1179(13) Uani 1 1 d . . . . .
H1AA H 0.104190 0.608510 1.155527 0.177 Uiso 1 1 calc R U . . .
H1AB H 0.212565 0.690064 1.232300 0.177 Uiso 1 1 calc R U . . .
H1AC H 0.135936 0.564519 1.237090 0.177 Uiso 1 1 calc R U . . .
C17 C 0.2059(10) 0.4358(8) 0.4115(6) 0.076(2) Uani 0.5 1 d . U P E 1
H17E H 0.115213 0.447430 0.390023 0.091 Uiso 0.5 1 calc R U P E 1
H17F H 0.287206 0.483433 0.388875 0.091 Uiso 0.5 1 calc R U P E 1
C18A C 0.3440(10) 0.0381(5) 1.1053(3) 0.093(2) Uani 0.6 1 d D . P F 1
H18A H 0.369395 0.057559 1.165963 0.111 Uiso 0.6 1 calc R U P F 1
H18B H 0.429314 0.075593 1.079984 0.111 Uiso 0.6 1 calc R U P F 1
C19A C 0.3050(10) -0.0911(6) 1.0752(5) 0.097(2) Uani 0.6 1 d D . P F 1
H19A H 0.210909 -0.126923 1.093397 0.117 Uiso 0.6 1 calc R U P F 1
H19B H 0.292849 -0.108375 1.014121 0.117 Uiso 0.6 1 calc R U P F 1
C20A C 0.4085(8) -0.1365(5) 1.1043(3) 0.198(3) Uani 1 1 d D . . . .
H20A H 0.503453 -0.098883 1.089438 0.298 Uiso 0.6 1 calc R U P F 1
H20B H 0.380695 -0.214943 1.079341 0.298 Uiso 0.6 1 calc R U P F 1
H20C H 0.413493 -0.127471 1.164467 0.298 Uiso 0.6 1 calc R U P F 1
H20D H 0.407792 -0.186878 1.052825 0.298 Uiso 0.4 1 calc R U P F 2
H20E H 0.329577 -0.171444 1.134053 0.298 Uiso 0.4 1 calc R U P F 2
H20F H 0.501396 -0.119036 1.138683 0.298 Uiso 0.4 1 calc R U P F 2
C18B C 0.2285(11) -0.0245(9) 1.1032(5) 0.093(3) Uani 0.4 1 d D . P F 2
H18C H 0.152419 -0.089167 1.070009 0.111 Uiso 0.4 1 calc R U P F 2
H18D H 0.218023 -0.023470 1.162301 0.111 Uiso 0.4 1 calc R U P F 2
H3 H 0.241(2) 0.5627(18) 0.9528(15) 0.053(6) Uiso 1 1 d . . . . .
H3A H 0.082(3) -0.071(2) 0.5387(18) 0.087(8) Uiso 1 1 d . . . . .
H6 H 0.241(3) 0.760(2) 0.6344(16) 0.072(7) Uiso 1 1 d . . . . .
H6B H 0.205(3) 0.364(2) 0.6915(18) 0.080(8) Uiso 1 1 d . . . . .
H6A H 0.185(3) 0.302(2) 0.8583(16) 0.076(8) Uiso 1 1 d . . . . .
H6AA H 0.168(3) -0.054(3) 0.899(2) 0.104(10) Uiso 1 1 d . . . . .
H6AB H 0.167(3) -0.124(2) 0.7989(18) 0.079(8) Uiso 1 1 d . . . . .
H6C H 0.221(3) 0.391(3) 0.597(2) 0.096(10) Uiso 1 1 d . . . . .
C19B C 0.3878(14) -0.0318(13) 1.0848(9) 0.124(5) Uani 0.4 1 d D . P F 2
H19C H 0.398611 -0.030081 1.025981 0.148 Uiso 0.4 1 calc R U P F 2
H19D H 0.463201 0.032580 1.118839 0.148 Uiso 0.4 1 calc R U P F 2
C17C C 0.2833(9) 0.4445(8) 0.4190(6) 0.068(2) Uani 0.5 1 d . U P E 2
H17G H 0.260789 0.491930 0.382585 0.081 Uiso 0.5 1 calc R U P E 2
H17H H 0.389146 0.456535 0.425351 0.081 Uiso 0.5 1 calc R U P E 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'
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
C8A N1A N2A 125.56(16) . . ?
C8A N1A C9A 123.91(18) . . ?
C9A N1A N2A 110.52(16) . . ?
C8 N1 N2 125.68(18) . . ?
C9 N1 N2 110.09(18) . . ?
C9 N1 C8 124.18(18) . . ?
C3A N2A N1A 100.42(17) . . ?
C3 N2 N1 100.53(18) . . ?
C8 N6 H6B 124.2(18) . . ?
C8 N6 H6C 114.0(18) . . ?
H6B N6 H6C 122(3) . . ?
C6 N5 C9 114.7(2) . . ?
C9 N4 C3 102.6(2) . . ?
C9A N4A C3A 102.55(18) . . ?
C8A N6A H6AA 114.0(18) . . ?
C8A N6A H6AB 123.5(16) . . ?
H6AA N6A H6AB 123(2) . . ?
C6A N5A C9A 114.60(18) . . ?
C14A N7A C2A 120.1(2) . . ?
C14A N7A C1A 119.5(2) . . ?
C2A N7A C1A 116.6(3) . . ?
C14 N7 C2 119.5(2) . . ?
C14 N7 C1 120.1(2) . . ?
C1 N7 C2 117.4(2) . . ?
N1A C8A C7A 114.76(17) . . ?
N6A C8A N1A 118.75(19) . . ?
N6A C8A C7A 126.49(19) . . ?
N1 C8 C7 114.50(19) . . ?
N6 C8 N1 118.8(2) . . ?
N6 C8 C7 126.7(2) . . ?
C8A C7A C10A 121.66(18) . . ?
C6A C7A C8A 117.49(19) . . ?
C6A C7A C10A 120.8(2) . . ?
N5 C9 N1 121.8(2) . . ?
N4 C9 N1 109.16(18) . . ?
N4 C9 N5 129.0(2) . . ?
N4A C9A N1A 109.02(19) . . ?
N4A C9A N5A 128.63(19) . . ?
N5A C9A N1A 122.34(19) . . ?
C8 C7 C10 121.3(2) . . ?
C6 C7 C8 117.3(2) . . ?
C6 C7 C10 121.33(19) . . ?
N7 C14 C13 121.2(2) . . ?
N7 C14 C15 121.6(2) . . ?
C15 C14 C13 117.2(2) . . ?
C10A N3A C17A 119.9(2) . . ?
C15A C14A N7A 121.5(2) . . ?
C15A C14A C13A 116.6(2) . . ?
C13A C14A N7A 121.9(2) . . ?
N5A C6A C7A 126.9(2) . . ?
N5A C6A H6A 112.7(14) . . ?
C7A C6A H6A 120.4(14) . . ?
C14 C13 H13 119.4 . . ?
C12 C13 C14 121.2(2) . . ?
C12 C13 H13 119.4 . . ?
C16A C11A C10A 121.1(2) . . ?
C12A C11A C10A 122.2(2) . . ?
C12A C11A C16A 116.6(2) . . ?
C12 C11 C10 122.2(2) . . ?
C12 C11 C16 117.2(2) . . ?
C16 C11 C10 120.6(2) . . ?
C10 N3 C17 118.3(4) . . ?
C10 N3 C17C 118.9(4) . . ?
C13 C12 C11 121.8(2) . . ?
C13 C12 H12 119.1 . . ?
C11 C12 H12 119.1 . . ?
C14 C15 H15 119.7 . . ?
C16 C15 C14 120.6(2) . . ?
C16 C15 H15 119.7 . . ?
C7A C10A C11A 118.50(19) . . ?
N3A C10A C7A 117.9(2) . . ?
N3A C10A C11A 123.6(2) . . ?
N2A C3A N4A 117.5(2) . . ?
N2A C3A H3A 116.7(15) . . ?
N4A C3A H3A 125.8(15) . . ?
N5 C6 C7 127.3(2) . . ?
N5 C6 H6 115.2(16) . . ?
C7 C6 H6 117.4(16) . . ?
C7 C10 C11 117.5(2) . . ?
N3 C10 C7 118.9(2) . . ?
N3 C10 C11 123.6(2) . . ?
N2 C3 N4 117.6(2) . . ?
N2 C3 H3 119.6(13) . . ?
N4 C3 H3 122.8(13) . . ?
C11 C16 H16 119.0 . . ?
C15 C16 C11 122.0(2) . . ?
C15 C16 H16 119.0 . . ?
C14A C15A H15A 119.5 . . ?
C14A C15A C16A 121.1(2) . . ?
C16A C15A H15A 119.5 . . ?
C11A C16A C15A 122.2(2) . . ?
C11A C16A H16A 118.9 . . ?
C15A C16A H16A 118.9 . . ?
C14A C13A H13A 119.2 . . ?
C12A C13A C14A 121.6(2) . . ?
C12A C13A H13A 119.2 . . ?
C11A C12A C13A 121.9(3) . . ?
C11A C12A H12A 119.1 . . ?
C13A C12A H12A 119.1 . . ?
N7 C2 H2A 109.5 . . ?
N7 C2 H2B 109.5 . . ?
N7 C2 H2C 109.5 . . ?
H2A C2 H2B 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
H18E C18 H18F 107.4 . . ?
H18G C18 H18H 108.1 . . ?
C19 C18 H18E 108.3 . . ?
C19 C18 H18F 108.3 . . ?
C19 C18 H18G 109.6 . . ?
C19 C18 H18H 109.6 . . ?
C19 C18 C17C 110.3(4) . . ?
C17 C18 H18E 108.3 . . ?
C17 C18 H18F 108.3 . . ?
C17 C18 C19 115.8(4) . . ?
C17C C18 H18G 109.6 . . ?
C17C C18 H18H 109.6 . . ?
C18 C19 H19E 108.7 . . ?
C18 C19 H19F 108.7 . . ?
H19E C19 H19F 107.6 . . ?
C20 C19 C18 114.2(3) . . ?
C20 C19 H19E 108.7 . . ?
C20 C19 H19F 108.7 . . ?
N7A C2A H2AA 109.5 . . ?
N7A C2A H2AB 109.5 . . ?
N7A C2A H2AC 109.5 . . ?
H2AA C2A H2AB 109.5 . . ?
H2AA C2A H2AC 109.5 . . ?
H2AB C2A H2AC 109.5 . . ?
N3A C17A H17A 109.9 . . ?
N3A C17A H17B 109.9 . . ?
N3A C17A H17C 109.5 . . ?
N3A C17A H17D 109.5 . . ?
N3A C17A C18A 109.1(3) . . ?
H17A C17A H17B 108.3 . . ?
H17C C17A H17D 108.1 . . ?
C18A C17A H17A 109.9 . . ?
C18A C17A H17B 109.9 . . ?
C18B C17A N3A 110.5(4) . . ?
C18B C17A H17C 109.5 . . ?
C18B C17A H17D 109.5 . . ?
N7 C1 H1A 109.5 . . ?
N7 C1 H1B 109.5 . . ?
N7 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C19 C20 H20G 109.5 . . ?
C19 C20 H20H 109.5 . . ?
C19 C20 H20I 109.5 . . ?
H20G C20 H20H 109.5 . . ?
H20G C20 H20I 109.5 . . ?
H20H C20 H20I 109.5 . . ?
N7A C1A H1AA 109.5 . . ?
N7A C1A H1AB 109.5 . . ?
N7A C1A H1AC 109.5 . . ?
H1AA C1A H1AB 109.5 . . ?
H1AA C1A H1AC 109.5 . . ?
H1AB C1A H1AC 109.5 . . ?
N3 C17 H17E 109.3 . . ?
N3 C17 H17F 109.3 . . ?
C18 C17 N3 111.7(6) . . ?
C18 C17 H17E 109.3 . . ?
C18 C17 H17F 109.3 . . ?
H17E C17 H17F 107.9 . . ?
C17A C18A H18A 109.5 . . ?
C17A C18A H18B 109.5 . . ?
C17A C18A C19A 110.8(6) . . ?
H18A C18A H18B 108.1 . . ?
C19A C18A H18A 109.5 . . ?
C19A C18A H18B 109.5 . . ?
C18A C19A H19A 108.6 . . ?
C18A C19A H19B 108.6 . . ?
H19A C19A H19B 107.6 . . ?
C20A C19A C18A 114.6(7) . . ?
C20A C19A H19A 108.6 . . ?
C20A C19A H19B 108.6 . . ?
C19A C20A H20A 109.5 . . ?
C19A C20A H20B 109.5 . . ?
C19A C20A H20C 109.5 . . ?
H20A C20A H20B 109.5 . . ?
H20A C20A H20C 109.5 . . ?
H20B C20A H20C 109.5 . . ?
H20D C20A H20E 109.5 . . ?
H20D C20A H20F 109.5 . . ?
H20E C20A H20F 109.5 . . ?
C19B C20A H20D 109.5 . . ?
C19B C20A H20E 109.5 . . ?
C19B C20A H20F 109.5 . . ?
C17A C18B H18C 110.1 . . ?
C17A C18B H18D 110.1 . . ?
C17A C18B C19B 108.0(8) . . ?
H18C C18B H18D 108.4 . . ?
C19B C18B H18C 110.1 . . ?
C19B C18B H18D 110.1 . . ?
C20A C19B C18B 110.6(9) . . ?
C20A C19B H19C 109.5 . . ?
C20A C19B H19D 109.5 . . ?
C18B C19B H19C 109.5 . . ?
C18B C19B H19D 109.5 . . ?
H19C C19B H19D 108.1 . . ?
N3 C17C H17G 111.0 . . ?
N3 C17C H17H 111.0 . . ?
C18 C17C N3 104.0(5) . . ?
C18 C17C H17G 111.0 . . ?
C18 C17C H17H 111.0 . . ?
H17G C17C H17H 109.0 . . ?
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
N1A N2A 1.378(2) . ?
N1A C8A 1.371(3) . ?
N1A C9A 1.372(2) . ?
N1 N2 1.379(2) . ?
N1 C8 1.376(3) . ?
N1 C9 1.375(3) . ?
N2A C3A 1.323(3) . ?
N2 C3 1.320(3) . ?
N6 C8 1.315(3) . ?
N6 H6B 0.90(3) . ?
N6 H6C 0.98(3) . ?
N5 C9 1.340(3) . ?
N5 C6 1.330(3) . ?
N4 C9 1.330(3) . ?
N4 C3 1.351(3) . ?
N4A C9A 1.334(3) . ?
N4A C3A 1.355(3) . ?
N6A C8A 1.316(3) . ?
N6A H6AA 1.01(3) . ?
N6A H6AB 0.94(3) . ?
N5A C9A 1.342(3) . ?
N5A C6A 1.334(3) . ?
N7A C14A 1.389(3) . ?
N7A C2A 1.426(4) . ?
N7A C1A 1.443(4) . ?
N7 C14 1.388(3) . ?
N7 C2 1.446(3) . ?
N7 C1 1.432(3) . ?
C8A C7A 1.413(3) . ?
C8 C7 1.412(3) . ?
C7A C6A 1.397(3) . ?
C7A C10A 1.476(3) . ?
C7 C6 1.395(3) . ?
C7 C10 1.471(3) . ?
C14 C13 1.401(3) . ?
C14 C15 1.400(3) . ?
N3A C10A 1.294(3) . ?
N3A C17A 1.472(3) . ?
C14A C15A 1.380(3) . ?
C14A C13A 1.387(3) . ?
C6A H6A 0.99(3) . ?
C13 H13 0.9300 . ?
C13 C12 1.377(3) . ?
C11A C10A 1.492(3) . ?
C11A C16A 1.376(3) . ?
C11A C12A 1.371(3) . ?
C11 C12 1.382(3) . ?
C11 C10 1.500(3) . ?
C11 C16 1.390(3) . ?
N3 C10 1.282(3) . ?
N3 C17 1.497(10) . ?
N3 C17C 1.545(9) . ?
C12 H12 0.9300 . ?
C15 H15 0.9300 . ?
C15 C16 1.381(3) . ?
C3A H3A 1.02(3) . ?
C6 H6 0.94(3) . ?
C3 H3 0.98(2) . ?
C16 H16 0.9300 . ?
C15A H15A 0.9300 . ?
C15A C16A 1.387(3) . ?
C16A H16A 0.9300 . ?
C13A H13A 0.9300 . ?
C13A C12A 1.379(4) . ?
C12A H12A 0.9300 . ?
C2 H2A 0.9600 . ?
C2 H2B 0.9600 . ?
C2 H2C 0.9600 . ?
C18 H18E 0.9700 . ?
C18 H18F 0.9700 . ?
C18 H18G 0.9700 . ?
C18 H18H 0.9700 . ?
C18 C19 1.524(4) . ?
C18 C17 1.444(9) . ?
C18 C17C 1.542(10) . ?
C19 H19E 0.9700 . ?
C19 H19F 0.9700 . ?
C19 C20 1.481(4) . ?
C2A H2AA 0.9600 . ?
C2A H2AB 0.9600 . ?
C2A H2AC 0.9600 . ?
C17A H17A 0.9700 . ?
C17A H17B 0.9700 . ?
C17A H17C 0.9700 . ?
C17A H17D 0.9700 . ?
C17A C18A 1.533(8) . ?
C17A C18B 1.462(9) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C20 H20G 0.9600 . ?
C20 H20H 0.9600 . ?
C20 H20I 0.9600 . ?
C1A H1AA 0.9600 . ?
C1A H1AB 0.9600 . ?
C1A H1AC 0.9600 . ?
C17 H17E 0.9700 . ?
C17 H17F 0.9700 . ?
C18A H18A 0.9700 . ?
C18A H18B 0.9700 . ?
C18A C19A 1.556(8) . ?
C19A H19A 0.9700 . ?
C19A H19B 0.9700 . ?
C19A C20A 1.374(8) . ?
C20A H20A 0.9600 . ?
C20A H20B 0.9600 . ?
C20A H20C 0.9600 . ?
C20A H20D 0.9600 . ?
C20A H20E 0.9600 . ?
C20A H20F 0.9600 . ?
C20A C19B 1.484(13) . ?
C18B H18C 0.9700 . ?
C18B H18D 0.9700 . ?
C18B C19B 1.590(13) . ?
C19B H19C 0.9700 . ?
C19B H19D 0.9700 . ?
C17C H17G 0.9700 . ?
C17C H17H 0.9700 . ?
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
N1A N2A C3A N4A 0.3(3) . . . . ?
N1A C8A C7A C6A -2.0(3) . . . . ?
N1A C8A C7A C10A 179.6(2) . . . . ?
N1 N2 C3 N4 0.1(3) . . . . ?
N1 C8 C7 C6 -3.1(3) . . . . ?
N1 C8 C7 C10 175.0(2) . . . . ?
N2A N1A C8A N6A 3.2(3) . . . . ?
N2A N1A C8A C7A -176.91(19) . . . . ?
N2A N1A C9A N4A -0.2(3) . . . . ?
N2A N1A C9A N5A 178.5(2) . . . . ?
N2 N1 C8 N6 2.4(3) . . . . ?
N2 N1 C8 C7 -176.3(2) . . . . ?
N2 N1 C9 N5 -179.8(2) . . . . ?
N2 N1 C9 N4 0.1(3) . . . . ?
N6 C8 C7 C6 178.3(2) . . . . ?
N6 C8 C7 C10 -3.6(4) . . . . ?
N6A C8A C7A C6A 177.9(2) . . . . ?
N6A C8A C7A C10A -0.5(4) . . . . ?
N7A C14A C15A C16A 179.1(2) . . . . ?
N7A C14A C13A C12A -178.8(3) . . . . ?
N7 C14 C13 C12 179.8(2) . . . . ?
N7 C14 C15 C16 -179.3(2) . . . . ?
C8A N1A N2A C3A 179.2(2) . . . . ?
C8A N1A C9A N4A -179.5(2) . . . . ?
C8A N1A C9A N5A -0.7(3) . . . . ?
C8A C7A C6A N5A 0.4(4) . . . . ?
C8A C7A C10A N3A -3.9(4) . . . . ?
C8A C7A C10A C11A 175.3(2) . . . . ?
C8 N1 N2 C3 177.4(2) . . . . ?
C8 N1 C9 N5 2.6(4) . . . . ?
C8 N1 C9 N4 -177.5(2) . . . . ?
C8 C7 C6 N5 2.3(4) . . . . ?
C8 C7 C10 C11 -170.4(2) . . . . ?
C8 C7 C10 N3 6.3(4) . . . . ?
C9 N1 N2 C3 -0.1(2) . . . . ?
C9 N1 C8 N6 179.6(2) . . . . ?
C9 N1 C8 C7 0.9(3) . . . . ?
C9 N5 C6 C7 1.1(4) . . . . ?
C9 N4 C3 N2 0.0(3) . . . . ?
C9A N1A N2A C3A 0.0(2) . . . . ?
C9A N1A C8A N6A -177.7(2) . . . . ?
C9A N1A C8A C7A 2.3(3) . . . . ?
C9A N4A C3A N2A -0.4(3) . . . . ?
C9A N5A C6A C7A 1.2(4) . . . . ?
C14 C13 C12 C11 -0.5(4) . . . . ?
C14 C15 C16 C11 -0.3(4) . . . . ?
N3A C17A C18A C19A -68.9(6) . . . . ?
N3A C17A C18B C19B 73.7(10) . . . . ?
C14A C15A C16A C11A -0.6(4) . . . . ?
C14A C13A C12A C11A 0.1(4) . . . . ?
C6A N5A C9A N1A -1.0(3) . . . . ?
C6A N5A C9A N4A 177.5(2) . . . . ?
C6A C7A C10A N3A 177.8(2) . . . . ?
C6A C7A C10A C11A -3.1(4) . . . . ?
C13 C14 C15 C16 -0.4(4) . . . . ?
C12 C11 C10 C7 -84.5(3) . . . . ?
C12 C11 C10 N3 98.9(3) . . . . ?
C12 C11 C16 C15 0.6(4) . . . . ?
C15 C14 C13 C12 0.8(4) . . . . ?
C10A C7A C6A N5A 178.8(2) . . . . ?
C10A N3A C17A C18A -123.2(4) . . . . ?
C10A N3A C17A C18B -171.2(5) . . . . ?
C10A C11A C16A C15A -175.4(2) . . . . ?
C10A C11A C12A C13A 175.6(2) . . . . ?
C3A N4A C9A N1A 0.4(3) . . . . ?
C3A N4A C9A N5A -178.3(2) . . . . ?
C6 N5 C9 N1 -3.5(3) . . . . ?
C6 N5 C9 N4 176.6(2) . . . . ?
C6 C7 C10 C11 7.6(4) . . . . ?
C6 C7 C10 N3 -175.7(3) . . . . ?
C10 C7 C6 N5 -175.8(2) . . . . ?
C10 C11 C12 C13 179.7(2) . . . . ?
C10 C11 C16 C15 -179.2(2) . . . . ?
C10 N3 C17 C18 178.5(4) . . . . ?
C10 N3 C17C C18 -158.0(4) . . . . ?
C3 N4 C9 N1 -0.1(3) . . . . ?
C3 N4 C9 N5 179.8(3) . . . . ?
C16 C11 C12 C13 -0.2(4) . . . . ?
C16 C11 C10 C7 95.4(3) . . . . ?
C16 C11 C10 N3 -81.2(4) . . . . ?
C15A C14A C13A C12A 1.1(4) . . . . ?
C16A C11A C10A C7A -91.0(3) . . . . ?
C16A C11A C10A N3A 88.0(3) . . . . ?
C16A C11A C12A C13A -1.5(4) . . . . ?
C13A C14A C15A C16A -0.9(4) . . . . ?
C12A C11A C10A C7A 91.9(3) . . . . ?
C12A C11A C10A N3A -89.0(3) . . . . ?
C12A C11A C16A C15A 1.8(4) . . . . ?
C2 N7 C14 C13 176.1(2) . . . . ?
C2 N7 C14 C15 -5.0(4) . . . . ?
C19 C18 C17 N3 -161.6(4) . . . . ?
C19 C18 C17C N3 171.9(3) . . . . ?
C2A N7A C14A C15A -18.4(4) . . . . ?
C2A N7A C14A C13A 161.6(3) . . . . ?
C17A N3A C10A C7A 179.7(3) . . . . ?
C17A N3A C10A C11A 0.6(4) . . . . ?
C17A C18A C19A C20A -171.7(6) . . . . ?
C17A C18B C19B C20A -178.6(8) . . . . ?
C1 N7 C14 C13 16.4(4) . . . . ?
C1 N7 C14 C15 -164.7(3) . . . . ?
C1A N7A C14A C15A -175.5(3) . . . . ?
C1A N7A C14A C13A 4.5(4) . . . . ?
C17 N3 C10 C7 167.2(4) . . . . ?
C17 N3 C10 C11 -16.2(6) . . . . ?
C17 C18 C19 C20 85.2(5) . . . . ?
C17C N3 C10 C7 -161.9(4) . . . . ?
C17C N3 C10 C11 14.6(5) . . . . ?
C17C C18 C19 C20 56.1(5) . . . . ?
