#------------------------------------------------------------------------------
#$Date: 2023-03-04 19:32:12 +0100 (Sat 04 de Mar de 2023) $
#$Revision: 281516 $
#$URL: svn://www.crystallography.net/cod/cif/7/06/22/7062209.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_7062209
loop_
_publ_author_name
'Parakhin, Vladimir V.'
'Pokhvisneva, Galina V.'
'Ternikova, Tatyana V.'
'Shlykova, Nina I.'
'Samigullina, Aida I.'
'Nikitin, Sergei V.'
'Gordeev, Pavel B.'
'Smirnov, Gennady A.'
'Kon’kova, Tatyana S.'
'Lempert, David B.'
'Pivkina, Alla N.'
_publ_section_title
;
 Linking polynitro hexaazaisowurtzitane cages via an N,N'-methylene
 bridge: a promising strategy for designing energetic ensembles of CL-20
 derivatives and adjusting their properties
;
_journal_issue                   5
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              2444
_journal_page_last               2455
_journal_paper_doi               10.1039/D2NJ05332B
_journal_volume                  47
_journal_year                    2023
_chemical_formula_moiety         'C15 H18 N26 O16, C2 H3 N'
_chemical_formula_sum            'C17 H21 N27 O16'
_chemical_formula_weight         859.61
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2022-05-02
_audit_creation_method
;
Olex2 1.5
(compiled 2021.11.18 svn.ra9532c28 for OlexSys, GUI svn.r6429)
;
_audit_update_record
;
2022-09-22 deposited with the CCDC.	2022-12-09 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   8.0773(2)
_cell_length_b                   24.2356(5)
_cell_length_c                   31.9915(7)
_cell_measurement_reflns_used    18398
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      78.7930
_cell_measurement_theta_min      3.9000
_cell_volume                     6262.6(2)
_computing_cell_refinement       'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -65.00 -22.00   0.50   12.00    --  -48.76  66.00 149.00   86
  2  ω    -63.00 -38.00   0.50   35.00    --  -90.00  55.00 -37.00   50
  3  ω     40.00  65.00   0.50   35.00    --  111.50 -66.00  14.00   50
  4  ω     41.00  77.00   0.50   35.00    --  111.50-122.00 -53.00   72
  5  ω     65.00  97.00   0.50   35.00    --  111.50-151.00 145.00   64
  6  ω    131.00 158.00   0.50   35.00    --  111.50  66.00 149.00   54
  7  ω    114.00 139.00   0.50   35.00    --  111.50  55.00 -37.00   50
  8  ω   -114.00 -83.00   0.50   12.00    --  -48.76-125.00 120.00   62
  9  ω   -121.00 -39.00   0.50   12.00    --  -48.76 -38.00  30.00  164
 10  ω   -112.00 -74.00   0.50   12.00    --  -48.76-125.00  90.00   76
 11  ω    -51.00 -26.00   0.50   35.00    --  -90.00  45.00-120.00   50
 12  ω     41.00  89.00   0.50   35.00    --  111.50 -78.00 167.15   96
 13  ω    140.00 175.00   0.50   35.00    --  111.50  30.00  60.00   70
 14  ω     54.00 103.00   0.50   35.00    --  111.50 -95.00 -60.00   98
 15  ω    124.00 155.00   0.50   35.00    --  111.50  77.00  60.00   62
 16  ω    143.00 178.00   0.50   35.00    --  111.50  29.00 -48.34   70
 17  ω    100.00 157.00   0.50   35.00    --  111.50  52.00  89.77  114
 18  ω     43.00  68.00   0.50   35.00    --  111.50 -95.00 -90.00   50
 19  ω     43.00  72.00   0.50   35.00    --  111.50 -78.00   9.92   58
 20  ω     48.00  84.00   0.50   35.00    --  111.50-125.00-120.00   72
 21  ω    135.00 161.00   0.50   35.00    --  111.50  30.00 -30.00   52
 22  ω     79.00 105.00   0.50   35.00    --  111.50 -77.00  60.00   52
 23  ω     40.00  74.00   0.50   35.00    --  111.50 -77.00  60.00   68
 24  ω     40.00  96.00   0.50   35.00    --  111.50 -95.00 150.00  112
 25  ω    101.00 129.00   0.50   35.00    --  111.50  29.00 -48.34   56
 26  ω    108.00 134.00   0.50   35.00    --  111.50  30.00 -30.00   52
 27  ω     40.00  66.00   0.50   35.00    --  111.50 -61.00  30.00   52
 28  ω     44.00  69.00   0.50   35.00    --  111.50 -61.00-150.00   50
 29  ω     45.00  71.00   0.50   35.00    --  111.50 -77.00-120.00   52
 30  ω     74.00  99.00   0.50   35.00    --  111.50 -95.00 -30.00   50
 31  ω    102.00 128.00   0.50   35.00    --  111.50  45.00 -30.00   52
 32  ω     98.00 124.00   0.50   35.00    --  111.50 125.00  60.00   52
 33  ω     57.00  83.00   0.50   35.00    --  111.50 -95.00   0.00   52
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0417331000
_diffrn_orient_matrix_UB_12      -0.0617038000
_diffrn_orient_matrix_UB_13      -0.0049690000
_diffrn_orient_matrix_UB_21      0.1192379000
_diffrn_orient_matrix_UB_22      0.0139742000
_diffrn_orient_matrix_UB_23      -0.0360659000
_diffrn_orient_matrix_UB_31      0.1428963000
_diffrn_orient_matrix_UB_32      0.0063314000
_diffrn_orient_matrix_UB_33      0.0315025000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0789
_diffrn_reflns_av_unetI/netI     0.0479
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       40
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_number            42994
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         80.199
_diffrn_reflns_theta_min         3.648
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.415
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.61749
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.123a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.823
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             3520
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: acetonitrile'
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.409
_refine_diff_density_min         -0.525
_refine_diff_density_rms         0.107
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     542
_refine_ls_number_reflns         6726
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.072
_refine_ls_R_factor_all          0.0664
_refine_ls_R_factor_gt           0.0591
_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)+(0.0928P)²+5.2137P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1578
_refine_ls_wR_factor_ref         0.1639
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5719
_reflns_number_total             6726
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2nj05332b2.cif
_cod_data_source_block           9
_cod_depositor_comments
'Adding full bibliography for 7062208--7062213.cif.'
_cod_database_code               7062209
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C11 H10 N O'
_chemical_oxdiff_usercomment     SNV7039
_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.
;
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C8(H8), C9(H9), C10(H10),
 C11(H11), C12(H12), C13(H13)
2.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C14(H14A,H14B), C15(H15A,H15B)
2.c Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C)
;
_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 2.863
_oxdiff_exptl_absorpt_empirical_full_min 0.403
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, 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
O1 O 0.2966(2) 0.86124(6) 0.32361(5) 0.0292(4) Uani 1 1 d . . . . .
O2 O 0.5594(2) 0.84565(7) 0.33525(6) 0.0306(4) Uani 1 1 d . . . . .
O3 O 0.1960(3) 0.77145(7) 0.24489(6) 0.0390(4) Uani 1 1 d . . . . .
O4 O 0.3822(3) 0.71050(8) 0.22791(6) 0.0404(5) Uani 1 1 d . . . . .
O5 O 0.2487(2) 0.72206(9) 0.47048(6) 0.0389(4) Uani 1 1 d . . . . .
O6 O 0.0157(2) 0.73965(8) 0.43904(6) 0.0381(4) Uani 1 1 d . . . . .
O7 O 0.0476(2) 0.57708(7) 0.37190(6) 0.0314(4) Uani 1 1 d . . . . .
O8 O -0.1101(2) 0.64969(8) 0.37609(6) 0.0370(4) Uani 1 1 d . . . . .
O9 O 0.2993(2) 0.44665(7) 0.25700(5) 0.0278(4) Uani 1 1 d . . . . .
O10 O 0.4833(2) 0.38100(7) 0.25826(5) 0.0308(4) Uani 1 1 d . . . . .
O11 O 0.8604(2) 0.59334(6) 0.29267(5) 0.0306(4) Uani 1 1 d . . . . .
O12 O 1.0091(2) 0.51817(7) 0.29009(5) 0.0296(4) Uani 1 1 d . . . . .
O13 O 0.3948(2) 0.35265(7) 0.40137(6) 0.0347(4) Uani 1 1 d . . . . .
O14 O 0.5743(2) 0.32149(7) 0.35608(6) 0.0316(4) Uani 1 1 d . . . . .
O15 O 1.0451(2) 0.44524(9) 0.38862(6) 0.0406(5) Uani 1 1 d . . . . .
O16 O 0.9238(2) 0.48973(8) 0.43928(5) 0.0346(4) Uani 1 1 d . . . . .
N1 N 0.3812(2) 0.77653(7) 0.34019(6) 0.0248(4) Uani 1 1 d . . . . .
N2 N 0.2881(2) 0.71203(7) 0.29401(6) 0.0254(4) Uani 1 1 d . . . . .
N3 N 0.2468(2) 0.72604(8) 0.40083(6) 0.0248(4) Uani 1 1 d . . . . .
N4 N 0.1548(2) 0.65915(7) 0.35539(6) 0.0234(4) Uani 1 1 d . . . . .
N5 N 0.5360(2) 0.71135(8) 0.38189(6) 0.0240(4) Uani 1 1 d . . . . .
N6 N 0.4305(2) 0.63811(7) 0.33106(6) 0.0230(4) Uani 1 1 d . . . . .
N7 N 0.4153(2) 0.83137(7) 0.33179(6) 0.0242(4) Uani 1 1 d . . . . .
N8 N 0.2919(3) 0.73376(8) 0.25305(7) 0.0315(5) Uani 1 1 d . . . . .
N9 N 0.1628(3) 0.72841(8) 0.43943(7) 0.0301(4) Uani 1 1 d . . . . .
N10 N 0.0224(2) 0.62711(8) 0.36964(7) 0.0271(4) Uani 1 1 d . . . . .
N11 N 0.5599(3) 0.79416(9) 0.42382(7) 0.0335(5) Uani 1 1 d . . . . .
N12 N 0.6617(3) 0.82969(9) 0.43454(7) 0.0338(5) Uani 1 1 d . . . . .
N13 N 0.7419(3) 0.86537(10) 0.44485(8) 0.0426(6) Uani 1 1 d . . . . .
N14 N 0.5122(2) 0.45419(7) 0.30088(6) 0.0202(4) Uani 1 1 d . . . . .
N15 N 0.7560(2) 0.51618(7) 0.31872(6) 0.0202(4) Uani 1 1 d . . . . .
N16 N 0.5416(2) 0.41159(7) 0.36371(6) 0.0219(4) Uani 1 1 d . . . . .
N17 N 0.7846(2) 0.47223(8) 0.38111(6) 0.0224(4) Uani 1 1 d . . . . .
N18 N 0.5047(2) 0.49613(8) 0.40348(6) 0.0243(4) Uani 1 1 d . . . . .
N19 N 0.4746(2) 0.54371(7) 0.33385(6) 0.0212(4) Uani 1 1 d . . . . .
N20 N 0.4243(2) 0.42449(8) 0.27051(6) 0.0229(4) Uani 1 1 d . . . . .
N21 N 0.8849(2) 0.54409(8) 0.30001(6) 0.0247(4) Uani 1 1 d . . . . .
N22 N 0.4986(2) 0.35867(8) 0.37388(6) 0.0266(4) Uani 1 1 d . . . . .
N23 N 0.9281(2) 0.46990(8) 0.40406(7) 0.0281(4) Uani 1 1 d . . . . .
N24 N 0.3228(3) 0.48679(9) 0.46267(7) 0.0335(5) Uani 1 1 d . . . . .
N25 N 0.2714(3) 0.53502(10) 0.45979(7) 0.0336(5) Uani 1 1 d . . . . .
N26 N 0.2094(3) 0.57754(11) 0.45825(8) 0.0426(6) Uani 1 1 d . . . . .
N27 N 0.3944(3) 0.38821(10) 0.53832(8) 0.0437(6) Uani 1 1 d . . . . .
C1 C 0.2297(3) 0.75099(9) 0.32594(7) 0.0250(5) Uani 1 1 d . . . . .
H1 H 0.152336 0.778870 0.313707 0.030 Uiso 1 1 calc R U . . .
C2 C 0.1456(3) 0.71859(9) 0.36348(8) 0.0250(5) Uani 1 1 d . . . . .
H2 H 0.028953 0.730950 0.368155 0.030 Uiso 1 1 calc R U . . .
C3 C 0.4502(3) 0.68939(9) 0.30989(7) 0.0245(4) Uani 1 1 d . . . . .
H3 H 0.529951 0.685104 0.286201 0.029 Uiso 1 1 calc R U . . .
C4 C 0.3254(3) 0.64105(9) 0.36697(7) 0.0236(4) Uani 1 1 d . . . . .
H4 H 0.321243 0.604417 0.381311 0.028 Uiso 1 1 calc R U . . .
C5 C 0.5149(3) 0.73480(9) 0.34132(8) 0.0241(4) Uani 1 1 d . . . . .
H5 H 0.621344 0.751022 0.331133 0.029 Uiso 1 1 calc R U . . .
C6 C 0.3886(3) 0.68659(9) 0.39805(7) 0.0237(4) Uani 1 1 d . . . . .
H6 H 0.410991 0.669946 0.426087 0.028 Uiso 1 1 calc R U . . .
C7 C 0.6386(3) 0.74114(9) 0.41066(8) 0.0285(5) Uani 1 1 d . . . . .
H7A H 0.746645 0.749016 0.397335 0.034 Uiso 1 1 calc R U . . .
H7B H 0.659177 0.718033 0.435638 0.034 Uiso 1 1 calc R U . . .
C8 C 0.7858(3) 0.46183(8) 0.33643(7) 0.0212(4) Uani 1 1 d . . . . .
H8 H 0.893188 0.445732 0.326797 0.025 Uiso 1 1 calc R U . . .
C9 C 0.6329(3) 0.42321(8) 0.32548(7) 0.0207(4) Uani 1 1 d . . . . .
H9 H 0.668451 0.388629 0.310994 0.025 Uiso 1 1 calc R U . . .
C10 C 0.6423(3) 0.54656(8) 0.34727(7) 0.0209(4) Uani 1 1 d . . . . .
H10 H 0.677868 0.585950 0.349748 0.025 Uiso 1 1 calc R U . . .
C11 C 0.6631(3) 0.51660(9) 0.39015(7) 0.0228(4) Uani 1 1 d . . . . .
H11 H 0.708978 0.542638 0.411457 0.027 Uiso 1 1 calc R U . . .
C12 C 0.4122(3) 0.48873(8) 0.33032(7) 0.0214(4) Uani 1 1 d . . . . .
H12 H 0.293429 0.489271 0.321533 0.026 Uiso 1 1 calc R U . . .
C13 C 0.4313(3) 0.45888(9) 0.37363(7) 0.0227(4) Uani 1 1 d . . . . .
H13 H 0.321454 0.445474 0.383862 0.027 Uiso 1 1 calc R U . . .
C14 C 0.4922(3) 0.47931(10) 0.44669(7) 0.0287(5) Uani 1 1 d . . . . .
H14A H 0.570070 0.501367 0.463786 0.034 Uiso 1 1 calc R U . . .
H14B H 0.524126 0.440006 0.449230 0.034 Uiso 1 1 calc R U . . .
C15 C 0.4177(3) 0.58741(9) 0.30651(7) 0.0234(4) Uani 1 1 d . . . . .
H15A H 0.301690 0.580862 0.297822 0.028 Uiso 1 1 calc R U . . .
H15B H 0.487907 0.589669 0.281203 0.028 Uiso 1 1 calc R U . . .
C16 C 0.2857(4) 0.37944(11) 0.51656(9) 0.0360(6) Uani 1 1 d . . . . .
C17 C 0.1468(4) 0.36865(15) 0.48925(10) 0.0481(7) Uani 1 1 d . . . . .
H17A H 0.097900 0.332850 0.496338 0.072 Uiso 1 1 calc R U . . .
H17B H 0.184871 0.368065 0.460165 0.072 Uiso 1 1 calc R U . . .
H17C H 0.063616 0.397712 0.492733 0.072 Uiso 1 1 calc R U . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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
N7 N1 C1 121.25(18) . . ?
N7 N1 C5 121.07(18) . . ?
C1 N1 C5 109.45(17) . . ?
N8 N2 C1 114.36(17) . . ?
N8 N2 C3 115.43(19) . . ?
C1 N2 C3 106.18(17) . . ?
N9 N3 C2 116.93(18) . . ?
N9 N3 C6 116.53(18) . . ?
C2 N3 C6 107.55(17) . . ?
N10 N4 C2 116.76(18) . . ?
N10 N4 C4 117.50(17) . . ?
C2 N4 C4 106.95(17) . . ?
C5 N5 C6 113.38(18) . . ?
C5 N5 C7 116.88(18) . . ?
C6 N5 C7 117.42(19) . . ?
C3 N6 C4 113.88(17) . . ?
C3 N6 C15 119.07(18) . . ?
C4 N6 C15 115.56(18) . . ?
O1 N7 N1 116.86(18) . . ?
O2 N7 O1 126.63(19) . . ?
O2 N7 N1 116.42(18) . . ?
O3 N8 N2 117.5(2) . . ?
O4 N8 O3 125.5(2) . . ?
O4 N8 N2 116.8(2) . . ?
O5 N9 N3 115.7(2) . . ?
O6 N9 O5 126.1(2) . . ?
O6 N9 N3 118.0(2) . . ?
O7 N10 N4 116.11(19) . . ?
O8 N10 O7 125.2(2) . . ?
O8 N10 N4 118.49(19) . . ?
N12 N11 C7 113.2(2) . . ?
N13 N12 N11 173.4(3) . . ?
N20 N14 C9 116.58(16) . . ?
N20 N14 C12 116.74(17) . . ?
C9 N14 C12 107.97(16) . . ?
N21 N15 C8 119.28(17) . . ?
N21 N15 C10 119.29(16) . . ?
C8 N15 C10 108.10(17) . . ?
N22 N16 C9 120.66(18) . . ?
N22 N16 C13 121.36(18) . . ?
C9 N16 C13 109.51(16) . . ?
N23 N17 C8 120.93(18) . . ?
N23 N17 C11 118.91(18) . . ?
C8 N17 C11 108.79(17) . . ?
C11 N18 C13 112.68(18) . . ?
C11 N18 C14 116.31(19) . . ?
C13 N18 C14 115.37(19) . . ?
C10 N19 C12 113.87(17) . . ?
C10 N19 C15 116.66(17) . . ?
C12 N19 C15 121.49(18) . . ?
O9 N20 N14 115.95(17) . . ?
O10 N20 O9 125.98(19) . . ?
O10 N20 N14 117.92(18) . . ?
O11 N21 N15 115.91(19) . . ?
O12 N21 O11 125.33(19) . . ?
O12 N21 N15 118.64(18) . . ?
O13 N22 O14 125.9(2) . . ?
O13 N22 N16 117.16(19) . . ?
O14 N22 N16 116.81(19) . . ?
O15 N23 O16 125.8(2) . . ?
O15 N23 N17 117.2(2) . . ?
O16 N23 N17 116.9(2) . . ?
N25 N24 C14 113.6(2) . . ?
N26 N25 N24 173.4(3) . . ?
N1 C1 N2 102.86(18) . . ?
N1 C1 H1 111.3 . . ?
N1 C1 C2 109.60(19) . . ?
N2 C1 H1 111.3 . . ?
N2 C1 C2 110.22(17) . . ?
C2 C1 H1 111.3 . . ?
N3 C2 N4 103.76(17) . . ?
N3 C2 C1 108.59(18) . . ?
N3 C2 H2 111.6 . . ?
N4 C2 C1 109.34(18) . . ?
N4 C2 H2 111.6 . . ?
C1 C2 H2 111.6 . . ?
N2 C3 H3 110.0 . . ?
N2 C3 C5 104.37(17) . . ?
N6 C3 N2 112.36(18) . . ?
N6 C3 H3 110.0 . . ?
N6 C3 C5 110.02(19) . . ?
C5 C3 H3 110.0 . . ?
N4 C4 H4 110.1 . . ?
N4 C4 C6 104.52(17) . . ?
N6 C4 N4 111.31(18) . . ?
N6 C4 H4 110.1 . . ?
N6 C4 C6 110.51(18) . . ?
C6 C4 H4 110.1 . . ?
N1 C5 C3 102.65(17) . . ?
N1 C5 H5 110.5 . . ?
N5 C5 N1 112.43(19) . . ?
N5 C5 C3 109.93(17) . . ?
N5 C5 H5 110.5 . . ?
C3 C5 H5 110.5 . . ?
N3 C6 C4 103.76(17) . . ?
N3 C6 H6 110.1 . . ?
N5 C6 N3 113.02(18) . . ?
N5 C6 C4 109.68(18) . . ?
N5 C6 H6 110.1 . . ?
C4 C6 H6 110.1 . . ?
N5 C7 N11 111.60(19) . . ?
N5 C7 H7A 109.3 . . ?
N5 C7 H7B 109.3 . . ?
N11 C7 H7A 109.3 . . ?
N11 C7 H7B 109.3 . . ?
H7A C7 H7B 108.0 . . ?
N15 C8 H8 112.1 . . ?
N15 C8 C9 108.63(17) . . ?
N17 C8 N15 103.02(17) . . ?
N17 C8 H8 112.1 . . ?
N17 C8 C9 108.32(17) . . ?
C9 C8 H8 112.1 . . ?
N14 C9 C8 109.55(16) . . ?
N14 C9 H9 111.9 . . ?
N16 C9 N14 102.36(16) . . ?
N16 C9 C8 108.83(17) . . ?
N16 C9 H9 111.9 . . ?
C8 C9 H9 111.9 . . ?
N15 C10 H10 110.1 . . ?
N15 C10 C11 104.04(16) . . ?
N19 C10 N15 112.21(17) . . ?
N19 C10 H10 110.1 . . ?
N19 C10 C11 110.18(17) . . ?
C11 C10 H10 110.1 . . ?
N17 C11 C10 103.70(16) . . ?
N17 C11 H11 110.2 . . ?
N18 C11 N17 113.35(18) . . ?
N18 C11 C10 109.00(17) . . ?
N18 C11 H11 110.2 . . ?
C10 C11 H11 110.2 . . ?
N14 C12 H12 110.4 . . ?
N14 C12 C13 104.15(16) . . ?
N19 C12 N14 112.40(17) . . ?
N19 C12 H12 110.4 . . ?
N19 C12 C13 108.99(17) . . ?
C13 C12 H12 110.4 . . ?
N16 C13 C12 103.05(17) . . ?
N16 C13 H13 110.6 . . ?
N18 C13 N16 112.22(18) . . ?
N18 C13 C12 109.64(17) . . ?
N18 C13 H13 110.6 . . ?
C12 C13 H13 110.6 . . ?
N18 C14 N24 111.2(2) . . ?
N18 C14 H14A 109.4 . . ?
N18 C14 H14B 109.4 . . ?
N24 C14 H14A 109.4 . . ?
N24 C14 H14B 109.4 . . ?
H14A C14 H14B 108.0 . . ?
N6 C15 H15A 110.6 . . ?
N6 C15 H15B 110.6 . . ?
N19 C15 N6 105.53(17) . . ?
N19 C15 H15A 110.6 . . ?
N19 C15 H15B 110.6 . . ?
H15A C15 H15B 108.8 . . ?
N27 C16 C17 179.4(4) . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
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
O1 N7 1.229(3) . ?
O2 N7 1.219(3) . ?
O3 N8 1.226(3) . ?
O4 N8 1.223(3) . ?
O5 N9 1.221(3) . ?
O6 N9 1.219(3) . ?
O7 N10 1.232(3) . ?
O8 N10 1.220(3) . ?
O9 N20 1.223(3) . ?
O10 N20 1.221(3) . ?
O11 N21 1.232(3) . ?
O12 N21 1.226(3) . ?
O13 N22 1.224(3) . ?
O14 N22 1.229(3) . ?
O15 N23 1.223(3) . ?
O16 N23 1.225(3) . ?
N1 N7 1.383(2) . ?
N1 C1 1.445(3) . ?
N1 C5 1.480(3) . ?
N2 N8 1.413(3) . ?
N2 C1 1.469(3) . ?
N2 C3 1.508(3) . ?
N3 N9 1.410(3) . ?
N3 C2 1.459(3) . ?
N3 C6 1.495(3) . ?
N4 N10 1.397(3) . ?
N4 C2 1.466(3) . ?
N4 C4 1.493(3) . ?
N5 C5 1.427(3) . ?
N5 C6 1.430(3) . ?
N5 C7 1.434(3) . ?
N6 C3 1.424(3) . ?
N6 C4 1.430(3) . ?
N6 C15 1.462(3) . ?
N11 N12 1.239(3) . ?
N11 C7 1.494(3) . ?
N12 N13 1.130(3) . ?
N14 N20 1.402(3) . ?
N14 C9 1.460(3) . ?
N14 C12 1.497(3) . ?
N15 N21 1.378(3) . ?
N15 C8 1.454(3) . ?
N15 C10 1.490(3) . ?
N16 N22 1.368(3) . ?
N16 C9 1.456(3) . ?
N16 C13 1.486(3) . ?
N17 N23 1.373(3) . ?
N17 C8 1.452(3) . ?
N17 C11 1.484(3) . ?
N18 C11 1.437(3) . ?
N18 C13 1.442(3) . ?
N18 C14 1.445(3) . ?
N19 C10 1.423(3) . ?
N19 C12 1.429(3) . ?
N19 C15 1.448(3) . ?
N24 N25 1.244(3) . ?
N24 C14 1.472(3) . ?
N25 N26 1.147(3) . ?
N27 C16 1.141(4) . ?
C1 H1 1.0000 . ?
C1 C2 1.587(3) . ?
C2 H2 1.0000 . ?
C3 H3 1.0000 . ?
C3 C5 1.580(3) . ?
C4 H4 1.0000 . ?
C4 C6 1.571(3) . ?
C5 H5 1.0000 . ?
C6 H6 1.0000 . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 H8 1.0000 . ?
C8 C9 1.588(3) . ?
C9 H9 1.0000 . ?
C10 H10 1.0000 . ?
C10 C11 1.561(3) . ?
C11 H11 1.0000 . ?
C12 H12 1.0000 . ?
C12 C13 1.571(3) . ?
C13 H13 1.0000 . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C17 1.445(4) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
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
N1 C1 C2 N3 1.3(2) . . . . ?
N1 C1 C2 N4 -111.3(2) . . . . ?
N2 C1 C2 N3 113.80(19) . . . . ?
N2 C1 C2 N4 1.2(2) . . . . ?
N2 C3 C5 N1 1.3(2) . . . . ?
N2 C3 C5 N5 121.09(18) . . . . ?
N4 C4 C6 N3 -0.1(2) . . . . ?
N4 C4 C6 N5 -121.11(19) . . . . ?
N6 C3 C5 N1 -119.49(19) . . . . ?
N6 C3 C5 N5 0.3(2) . . . . ?
N6 C4 C6 N3 119.74(19) . . . . ?
N6 C4 C6 N5 -1.3(2) . . . . ?
N7 N1 C1 N2 111.3(2) . . . . ?
N7 N1 C1 C2 -131.4(2) . . . . ?
N7 N1 C5 N5 115.3(2) . . . . ?
N7 N1 C5 C3 -126.6(2) . . . . ?
N8 N2 C1 N1 -91.5(2) . . . . ?
N8 N2 C1 C2 151.73(19) . . . . ?
N8 N2 C3 N6 -136.45(19) . . . . ?
N8 N2 C3 C5 104.4(2) . . . . ?
N9 N3 C2 N4 -97.4(2) . . . . ?
N9 N3 C2 C1 146.39(18) . . . . ?
N9 N3 C6 N5 -129.6(2) . . . . ?
N9 N3 C6 C4 111.6(2) . . . . ?
N10 N4 C2 N3 98.2(2) . . . . ?
N10 N4 C2 C1 -146.14(19) . . . . ?
N10 N4 C4 N6 129.03(19) . . . . ?
N10 N4 C4 C6 -111.7(2) . . . . ?
N12 N11 C7 N5 -153.7(2) . . . . ?
N14 C12 C13 N16 0.8(2) . . . . ?
N14 C12 C13 N18 120.47(18) . . . . ?
N15 C8 C9 N14 0.6(2) . . . . ?
N15 C8 C9 N16 -110.62(19) . . . . ?
N15 C10 C11 N17 -0.6(2) . . . . ?
N15 C10 C11 N18 -121.64(18) . . . . ?
N17 C8 C9 N14 111.78(19) . . . . ?
N17 C8 C9 N16 0.6(2) . . . . ?
N19 C10 C11 N17 119.84(18) . . . . ?
N19 C10 C11 N18 -1.2(2) . . . . ?
N19 C12 C13 N16 -119.35(18) . . . . ?
N19 C12 C13 N18 0.3(2) . . . . ?
N20 N14 C9 N16 -98.59(19) . . . . ?
N20 N14 C9 C8 146.04(18) . . . . ?
N20 N14 C12 N19 -130.88(19) . . . . ?
N20 N14 C12 C13 111.29(19) . . . . ?
N21 N15 C8 N17 106.2(2) . . . . ?
N21 N15 C8 C9 -139.06(18) . . . . ?
N21 N15 C10 N19 121.9(2) . . . . ?
N21 N15 C10 C11 -118.99(19) . . . . ?
N22 N16 C9 N14 113.3(2) . . . . ?
N22 N16 C9 C8 -130.8(2) . . . . ?
N22 N16 C13 N18 115.2(2) . . . . ?
N22 N16 C13 C12 -126.9(2) . . . . ?
N23 N17 C8 N15 -108.8(2) . . . . ?
N23 N17 C8 C9 136.24(19) . . . . ?
N23 N17 C11 N18 -118.8(2) . . . . ?
N23 N17 C11 C10 123.2(2) . . . . ?
N25 N24 C14 N18 -57.6(3) . . . . ?
C1 N1 N7 O1 21.5(3) . . . . ?
C1 N1 N7 O2 -161.9(2) . . . . ?
C1 N1 C5 N5 -95.9(2) . . . . ?
C1 N1 C5 C3 22.1(2) . . . . ?
C1 N2 N8 O3 -26.3(3) . . . . ?
C1 N2 N8 O4 159.0(2) . . . . ?
C1 N2 C3 N6 95.7(2) . . . . ?
C1 N2 C3 C5 -23.5(2) . . . . ?
C2 N3 N9 O5 164.0(2) . . . . ?
C2 N3 N9 O6 -20.2(3) . . . . ?
C2 N3 C6 N5 96.8(2) . . . . ?
C2 N3 C6 C4 -21.9(2) . . . . ?
C2 N4 N10 O7 -163.2(2) . . . . ?
C2 N4 N10 O8 21.6(3) . . . . ?
C2 N4 C4 N6 -97.4(2) . . . . ?
C2 N4 C4 C6 21.9(2) . . . . ?
C3 N2 N8 O3 -149.9(2) . . . . ?
C3 N2 N8 O4 35.3(3) . . . . ?
C3 N2 C1 N1 37.0(2) . . . . ?
C3 N2 C1 C2 -79.8(2) . . . . ?
C3 N6 C4 N4 60.6(2) . . . . ?
C3 N6 C4 C6 -55.1(2) . . . . ?
C3 N6 C15 N19 154.42(19) . . . . ?
C4 N4 N10 O7 -34.1(3) . . . . ?
C4 N4 N10 O8 150.7(2) . . . . ?
C4 N4 C2 N3 -35.8(2) . . . . ?
C4 N4 C2 C1 79.9(2) . . . . ?
C4 N6 C3 N2 -60.5(3) . . . . ?
C4 N6 C3 C5 55.4(2) . . . . ?
C4 N6 C15 N19 -64.4(2) . . . . ?
C5 N1 N7 O1 166.6(2) . . . . ?
C5 N1 N7 O2 -16.8(3) . . . . ?
C5 N1 C1 N2 -37.4(2) . . . . ?
C5 N1 C1 C2 79.9(2) . . . . ?
C5 N5 C6 N3 -58.0(2) . . . . ?
C5 N5 C6 C4 57.2(2) . . . . ?
C5 N5 C7 N11 68.5(3) . . . . ?
C6 N3 N9 O5 34.9(3) . . . . ?
C6 N3 N9 O6 -149.3(2) . . . . ?
C6 N3 C2 N4 36.0(2) . . . . ?
C6 N3 C2 C1 -80.3(2) . . . . ?
C6 N5 C5 N1 56.9(2) . . . . ?
C6 N5 C5 C3 -56.8(2) . . . . ?
C6 N5 C7 N11 -71.3(3) . . . . ?
C7 N5 C5 N1 -84.5(2) . . . . ?
C7 N5 C5 C3 161.82(18) . . . . ?
C7 N5 C6 N3 83.2(2) . . . . ?
C7 N5 C6 C4 -161.61(18) . . . . ?
C8 N15 N21 O11 -167.01(19) . . . . ?
C8 N15 N21 O12 16.7(3) . . . . ?
C8 N15 C10 N19 -97.4(2) . . . . ?
C8 N15 C10 C11 21.7(2) . . . . ?
C8 N17 N23 O15 -18.8(3) . . . . ?
C8 N17 N23 O16 165.68(19) . . . . ?
C8 N17 C11 N18 97.3(2) . . . . ?
C8 N17 C11 C10 -20.7(2) . . . . ?
C9 N14 N20 O9 163.65(18) . . . . ?
C9 N14 N20 O10 -20.5(3) . . . . ?
C9 N14 C12 N19 95.5(2) . . . . ?
C9 N14 C12 C13 -22.3(2) . . . . ?
C9 N16 N22 O13 -165.5(2) . . . . ?
C9 N16 N22 O14 18.1(3) . . . . ?
C9 N16 C13 N18 -96.6(2) . . . . ?
C9 N16 C13 C12 21.2(2) . . . . ?
C10 N15 N21 O11 -30.7(3) . . . . ?
C10 N15 N21 O12 153.02(19) . . . . ?
C10 N15 C8 N17 -34.5(2) . . . . ?
C10 N15 C8 C9 80.3(2) . . . . ?
C10 N19 C12 N14 -57.8(2) . . . . ?
C10 N19 C12 C13 57.2(2) . . . . ?
C10 N19 C15 N6 -63.1(2) . . . . ?
C11 N17 N23 O15 -158.2(2) . . . . ?
C11 N17 N23 O16 26.2(3) . . . . ?
C11 N17 C8 N15 34.3(2) . . . . ?
C11 N17 C8 C9 -80.7(2) . . . . ?
C11 N18 C13 N16 56.1(2) . . . . ?
C11 N18 C13 C12 -57.8(2) . . . . ?
C11 N18 C14 N24 150.6(2) . . . . ?
C12 N14 N20 O9 34.0(3) . . . . ?
C12 N14 N20 O10 -150.15(19) . . . . ?
C12 N14 C9 N16 35.1(2) . . . . ?
C12 N14 C9 C8 -80.2(2) . . . . ?
C12 N19 C10 N15 58.3(2) . . . . ?
C12 N19 C10 C11 -57.1(2) . . . . ?
C12 N19 C15 N6 149.96(19) . . . . ?
C13 N16 N22 O13 -20.9(3) . . . . ?
C13 N16 N22 O14 162.8(2) . . . . ?
C13 N16 C9 N14 -35.1(2) . . . . ?
C13 N16 C9 C8 80.8(2) . . . . ?
C13 N18 C11 N17 -56.8(2) . . . . ?
C13 N18 C11 C10 58.1(2) . . . . ?
C13 N18 C14 N24 -74.1(3) . . . . ?
C14 N18 C11 N17 79.7(2) . . . . ?
C14 N18 C11 C10 -165.42(18) . . . . ?
C14 N18 C13 N16 -80.8(2) . . . . ?
C14 N18 C13 C12 165.32(19) . . . . ?
C15 N6 C3 N2 81.4(2) . . . . ?
C15 N6 C3 C5 -162.82(18) . . . . ?
C15 N6 C4 N4 -82.6(2) . . . . ?
C15 N6 C4 C6 161.72(18) . . . . ?
C15 N19 C10 N15 -91.2(2) . . . . ?
C15 N19 C10 C11 153.41(18) . . . . ?
C15 N19 C12 N14 90.1(2) . . . . ?
C15 N19 C12 C13 -155.00(19) . . . . ?
