#------------------------------------------------------------------------------
#$Date: 2024-03-04 22:06:15 +0200 (Mon, 04 Mar 2024) $
#$Revision: 290139 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/79/7247916.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_7247916
loop_
_publ_author_name
'Jing, Suming'
'Deng, Jiahao'
'Li, Cong'
'Liu, Yucun'
'Zhu, Jin'
'Wang, Yuanyuan'
'Zhang, Wei'
'Liu, Jia'
_publ_section_title
;
 High energy explosive with low sensitivity: a new energetic cocrystal
 based on CL-20 and BMDNP
;
_journal_issue                   8
_journal_name_full               CrystEngComm
_journal_page_first              1126
_journal_page_last               1132
_journal_paper_doi               10.1039/D3CE01118F
_journal_volume                  26
_journal_year                    2024
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C4 H3 Br N4 O4, C6 H6 N12 O12'
_chemical_formula_sum            'C10 H9 Br N16 O16'
_chemical_formula_weight         689.24
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2022-11-28
_audit_creation_method
;
Olex2 1.5-ac5-024
(compiled 2022.04.12 svn.rca3783a0 for Rigaku Oxford Diffraction, GUI svn.r6498)
;
_audit_update_record
;
2023-10-23 deposited with the CCDC.	2023-12-25 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 96.5840(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.21640(10)
_cell_length_b                   12.1632(2)
_cell_length_c                   9.87540(10)
_cell_measurement_reflns_used    6173
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      76.0840
_cell_measurement_theta_min      3.6310
_cell_volume                     1099.74(2)
_computing_cell_refinement       'CrysAlisPro 1.171.42.70a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.70a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.70a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5-ac5-024 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-ac5-024 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/2 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_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 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    105.00 130.00   0.50    0.05    --  104.70 112.00 152.00   50
  2  ω    -26.00  13.00   0.50    0.05    --   47.73 -19.00   0.00   78
  3  ω     36.00  66.00   0.50    0.05    --  104.70 -61.00 120.00   60
  4  ω     39.00  69.00   0.50    0.05    --  104.70 -61.00  60.00   60
  5  ω     37.00  70.00   0.50    0.05    --  104.70 -61.00  30.00   66
  6  ω     34.00  63.00   0.50    0.05    --  104.70 -61.00-120.00   58
  7  ω     96.00 178.00   0.50    0.05    --  104.70  30.00-120.00  164
  8  ω     59.00 103.00   0.50    0.05    --  104.70 -77.00  90.00   88
  9  ω     54.00  87.00   0.50    0.05    --  104.70 -95.00  90.00   66
 10  ω     45.00 108.00   0.50    0.05    --  104.70-112.00  60.00  126
 11  ω      9.00  79.00   0.50    0.05    --   47.73-112.00  60.00  140
 12  ω    -39.00  -6.00   0.50    0.05    --  -47.73 112.00 152.00   66
 13  ω    -71.00 -45.00   0.50    0.05    --  -99.00 112.00 152.00   52
 14  ω   -103.00 -72.00   0.50    0.05    --  -99.00 112.00 152.00   62
 15  ω    -69.00 -29.00   0.50    0.05    --  -99.00  61.00 -60.00   80
 16  ω    -24.00   2.00   0.50    0.05    --  -47.73  19.00-180.00   52
 17  ω    -40.00  23.00   0.50    0.05    --  -47.73  38.00 -90.00  126
 18  ω    -21.00  21.00   0.50    0.05    --  -47.73  19.00 150.00   84
 19  ω    -65.00 -40.00   0.50    0.05    --  -99.00  61.00  30.00   50
 20  ω   -170.00-144.00   0.50    0.05    --  -99.00 -45.00  30.00   52
 21  ω   -167.00-100.00   0.50    0.05    --  -99.00 -45.00  90.00  134
 22  ω   -124.00 -90.00   0.50    0.05    --  -99.00 -45.00  30.00   68
 23  ω   -133.00 -86.00   0.50    0.05    --  -99.00-112.00  60.00   94
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1539074000
_diffrn_orient_matrix_UB_12      0.0347865000
_diffrn_orient_matrix_UB_13      -0.0298216000
_diffrn_orient_matrix_UB_21      0.0327723000
_diffrn_orient_matrix_UB_22      -0.1194654000
_diffrn_orient_matrix_UB_23      -0.0384165000
_diffrn_orient_matrix_UB_31      -0.0595209000
_diffrn_orient_matrix_UB_32      0.0238147000
_diffrn_orient_matrix_UB_33      -0.1493101000
_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  0.0217
_diffrn_reflns_av_unetI/netI     0.0268
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            6646
_diffrn_reflns_point_group_measured_fraction_full 0.846
_diffrn_reflns_point_group_measured_fraction_max 0.846
_diffrn_reflns_theta_full        66.531
_diffrn_reflns_theta_max         66.531
_diffrn_reflns_theta_min         4.507
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    3.698
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.87601
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.70a (Rigaku Oxford Diffraction, 2022)
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    2.081
_exptl_crystal_description       block
_exptl_crystal_F_000             688
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.377
_refine_diff_density_min         -0.332
_refine_diff_density_rms         0.053
_refine_ls_abs_structure_details
;
 Flack x determined using 1196 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.020(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     389
_refine_ls_number_reflns         3270
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.0215
_refine_ls_R_factor_gt           0.0211
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0362P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0556
_refine_ls_wR_factor_ref         0.0559
_reflns_Friedel_coverage         0.608
_reflns_Friedel_fraction_full    0.674
_reflns_Friedel_fraction_max     0.674
_reflns_number_gt                3217
_reflns_number_total             3270
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3ce01118f2.cif
_cod_data_source_block           2211177429-a
_cod_depositor_comments          'Adding full bibliography for 7247916.cif.'
_cod_database_code               7247916
_shelx_shelxl_version_number     2019/2
_chemical_oxdiff_formula         'C N'
_chemical_oxdiff_usercomment     2211177429-A
_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   0.626
_shelx_estimated_absorpt_t_min   0.525
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C7(H7), C8(H8), C10(H10)
2.b Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C)
;
_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 1.240
_oxdiff_exptl_absorpt_empirical_full_min 0.849
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, 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
Br1 Br 1.09243(4) 0.27384(3) 0.05449(3) 0.02256(11) Uani 1 1 d . . . . .
O5 O 1.2461(3) 0.4951(2) 0.0232(3) 0.0263(6) Uani 1 1 d . . . . .
O11 O 1.1962(3) 0.6497(2) 0.1191(3) 0.0250(6) Uani 1 1 d . . . . .
O15 O 0.8300(3) 0.2107(3) 0.2150(3) 0.0380(7) Uani 1 1 d . . . . .
O16 O 0.8017(3) 0.2873(3) 0.4083(3) 0.0330(7) Uani 1 1 d . . . . .
N1 N 1.0104(3) 0.5425(3) 0.2741(3) 0.0187(6) Uani 1 1 d . . . . .
N4 N 0.8502(3) 0.2856(3) 0.2982(3) 0.0244(7) Uani 1 1 d . . . . .
N8 N 1.1818(3) 0.5500(3) 0.1010(3) 0.0179(6) Uani 1 1 d . . . . .
N16 N 0.9219(3) 0.4726(3) 0.3272(3) 0.0204(7) Uani 1 1 d . . . . .
C1 C 0.9357(4) 0.3792(3) 0.2629(3) 0.0185(7) Uani 1 1 d . . . . .
C4 C 1.0804(4) 0.4922(3) 0.1772(3) 0.0173(7) Uani 1 1 d . . . . .
C6 C 1.0336(4) 0.3854(3) 0.1650(3) 0.0179(7) Uani 1 1 d . . . . .
C9 C 1.0173(4) 0.6554(3) 0.3235(4) 0.0254(8) Uani 1 1 d . . . . .
H9A H 0.978970 0.705003 0.249685 0.038 Uiso 1 1 calc R U . . .
H9B H 1.119008 0.674742 0.354202 0.038 Uiso 1 1 calc R U . . .
H9C H 0.958638 0.662509 0.399715 0.038 Uiso 1 1 calc R U . . .
O1 O 0.3580(3) 0.5259(2) 0.3552(3) 0.0215(6) Uani 1 1 d . . . . .
O2 O 0.5730(3) 0.2479(2) 0.5684(2) 0.0239(6) Uani 1 1 d . . . . .
O3 O 0.1330(3) 0.3832(2) 0.7473(3) 0.0213(5) Uani 1 1 d . . . . .
O4 O 0.3579(3) 0.2414(2) 0.6430(2) 0.0214(6) Uani 1 1 d . . . . .
O6 O 0.7828(3) 0.5640(2) 1.0299(2) 0.0211(5) Uani 1 1 d . . . . .
O7 O 0.1204(3) 0.5006(3) 0.5797(3) 0.0290(6) Uani 1 1 d . . . . .
O8 O 0.4903(3) 0.7827(2) 0.9172(2) 0.0250(5) Uani 1 1 d . . . . .
O9 O 0.8469(3) 0.6669(2) 0.5959(2) 0.0214(5) Uani 1 1 d . . . . .
O10 O 0.6899(2) 0.7879(2) 0.6524(2) 0.0202(5) Uani 1 1 d . . . . .
O12 O 0.9031(3) 0.4967(2) 0.8693(3) 0.0236(6) Uani 1 1 d . . . . .
O13 O 0.5850(3) 0.4786(3) 0.3455(3) 0.0259(6) Uani 1 1 d . . . . .
O14 O 0.5101(3) 0.6594(2) 1.0786(2) 0.0210(5) Uani 1 1 d . . . . .
N2 N 0.4809(3) 0.5024(2) 0.4050(3) 0.0175(6) Uani 1 1 d . . . . .
N3 N 0.7331(3) 0.6950(3) 0.6384(3) 0.0168(6) Uani 1 1 d . . . . .
N5 N 0.4994(3) 0.6879(3) 0.9605(3) 0.0180(6) Uani 1 1 d . . . . .
N6 N 0.5285(3) 0.3500(2) 0.7434(3) 0.0148(6) Uani 1 1 d . . . . .
N7 N 0.6509(3) 0.6087(2) 0.6873(3) 0.0157(6) Uani 1 1 d . . . . .
N9 N 0.6700(3) 0.4554(2) 0.8728(3) 0.0153(6) Uani 1 1 d . . . . .
N10 N 0.7933(3) 0.5098(3) 0.9273(3) 0.0175(7) Uani 1 1 d . . . . .
N11 N 0.5014(3) 0.4935(2) 0.5488(3) 0.0151(6) Uani 1 1 d . . . . .
N12 N 0.4926(3) 0.6045(2) 0.8623(3) 0.0155(6) Uani 1 1 d . . . . .
N13 N 0.3300(3) 0.4809(2) 0.7132(3) 0.0134(6) Uani 1 1 d . . . . .
N14 N 0.4828(3) 0.2757(3) 0.6446(2) 0.0179(6) Uani 1 1 d . . . . .
N15 N 0.1836(3) 0.4521(2) 0.6765(3) 0.0180(6) Uani 1 1 d . . . . .
C2 C 0.6639(4) 0.4103(3) 0.7366(3) 0.0157(7) Uani 1 1 d . . . . .
H2 H 0.747697 0.359552 0.727522 0.019 Uiso 1 1 calc R U . . .
C3 C 0.5249(3) 0.4933(3) 0.9035(3) 0.0151(7) Uani 1 1 d . . . . .
H3 H 0.512574 0.482043 1.001792 0.018 Uiso 1 1 calc R U . . .
C5 C 0.5033(3) 0.6334(3) 0.7211(3) 0.0139(7) Uani 1 1 d . . . . .
H5 H 0.477144 0.712266 0.702684 0.017 Uiso 1 1 calc R U . . .
C7 C 0.6488(4) 0.5015(3) 0.6196(3) 0.0156(7) Uani 1 1 d . . . . .
H7 H 0.725737 0.494714 0.556448 0.019 Uiso 1 1 calc R U . . .
C8 C 0.4214(4) 0.4151(3) 0.8093(3) 0.0140(7) Uani 1 1 d . . . . .
H8 H 0.361877 0.367379 0.864152 0.017 Uiso 1 1 calc R U . . .
C10 C 0.4012(4) 0.5543(3) 0.6277(3) 0.0136(7) Uani 1 1 d . . . . .
H10 H 0.327991 0.596898 0.565991 0.016 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'
Br Br -0.6763 1.2805 '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
N16 N1 C4 110.7(3) . . ?
N16 N1 C9 118.5(3) . . ?
C4 N1 C9 130.8(3) . . ?
O15 N4 C1 117.9(3) . . ?
O16 N4 O15 124.4(4) . . ?
O16 N4 C1 117.7(3) . . ?
O5 N8 O11 125.3(3) . . ?
O5 N8 C4 116.7(3) . . ?
O11 N8 C4 118.0(3) . . ?
C1 N16 N1 105.3(3) . . ?
N16 C1 N4 118.5(3) . . ?
N16 C1 C6 113.1(3) . . ?
C6 C1 N4 128.4(3) . . ?
N1 C4 N8 122.3(3) . . ?
N1 C4 C6 108.6(3) . . ?
C6 C4 N8 129.1(3) . . ?
C1 C6 Br1 128.3(3) . . ?
C4 C6 Br1 129.3(3) . . ?
C4 C6 C1 102.2(3) . . ?
N1 C9 H9A 109.5 . . ?
N1 C9 H9B 109.5 . . ?
N1 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
O1 N2 N11 115.8(3) . . ?
O13 N2 O1 127.6(3) . . ?
O13 N2 N11 116.4(3) . . ?
O9 N3 N7 115.1(3) . . ?
O10 N3 O9 127.4(3) . . ?
O10 N3 N7 117.2(3) . . ?
O8 N5 N12 116.3(3) . . ?
O14 N5 O8 126.8(3) . . ?
O14 N5 N12 116.9(3) . . ?
N14 N6 C2 119.8(3) . . ?
N14 N6 C8 120.4(3) . . ?
C2 N6 C8 111.8(3) . . ?
N3 N7 C5 118.2(3) . . ?
N3 N7 C7 119.0(3) . . ?
C7 N7 C5 108.8(3) . . ?
N10 N9 C2 119.3(3) . . ?
N10 N9 C3 119.9(3) . . ?
C2 N9 C3 111.7(3) . . ?
O6 N10 O12 127.2(3) . . ?
O6 N10 N9 116.4(3) . . ?
O12 N10 N9 116.4(3) . . ?
N2 N11 C7 119.1(3) . . ?
N2 N11 C10 118.2(3) . . ?
C7 N11 C10 108.6(3) . . ?
N5 N12 C3 119.7(3) . . ?
N5 N12 C5 119.1(3) . . ?
C3 N12 C5 117.8(3) . . ?
N15 N13 C8 120.4(3) . . ?
N15 N13 C10 119.6(2) . . ?
C8 N13 C10 117.4(3) . . ?
O2 N14 N6 116.5(3) . . ?
O4 N14 O2 126.8(3) . . ?
O4 N14 N6 116.7(3) . . ?
O3 N15 N13 116.4(3) . . ?
O7 N15 O3 127.3(3) . . ?
O7 N15 N13 116.3(3) . . ?
N6 C2 H2 111.6 . . ?
N6 C2 C7 112.3(3) . . ?
N9 C2 N6 95.1(2) . . ?
N9 C2 H2 111.6 . . ?
N9 C2 C7 113.6(3) . . ?
C7 C2 H2 111.6 . . ?
N9 C3 H3 111.2 . . ?
N9 C3 C8 101.0(3) . . ?
N12 C3 N9 113.6(3) . . ?
N12 C3 H3 111.2 . . ?
N12 C3 C8 108.1(3) . . ?
C8 C3 H3 111.2 . . ?
N7 C5 H5 111.4 . . ?
N7 C5 C10 104.4(3) . . ?
N12 C5 N7 109.6(3) . . ?
N12 C5 H5 111.4 . . ?
N12 C5 C10 108.2(3) . . ?
C10 C5 H5 111.4 . . ?
N7 C7 C2 107.0(3) . . ?
N7 C7 H7 112.6 . . ?
N11 C7 N7 104.0(3) . . ?
N11 C7 C2 107.5(3) . . ?
N11 C7 H7 112.6 . . ?
C2 C7 H7 112.6 . . ?
N6 C8 C3 101.2(2) . . ?
N6 C8 H8 111.4 . . ?
N13 C8 N6 112.2(2) . . ?
N13 C8 C3 108.9(3) . . ?
N13 C8 H8 111.4 . . ?
C3 C8 H8 111.4 . . ?
N11 C10 C5 104.4(3) . . ?
N11 C10 H10 111.0 . . ?
N13 C10 N11 110.7(3) . . ?
N13 C10 C5 108.6(3) . . ?
N13 C10 H10 111.0 . . ?
C5 C10 H10 111.0 . . ?
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
Br1 C6 1.861(4) . ?
O5 N8 1.222(4) . ?
O11 N8 1.230(4) . ?
O15 N4 1.227(5) . ?
O16 N4 1.222(4) . ?
N1 N16 1.327(4) . ?
N1 C4 1.359(5) . ?
N1 C9 1.457(5) . ?
N4 C1 1.449(5) . ?
N8 C4 1.448(5) . ?
N16 C1 1.315(5) . ?
C1 C6 1.399(5) . ?
C4 C6 1.369(6) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
O1 N2 1.216(4) . ?
O2 N14 1.231(4) . ?
O3 N15 1.217(4) . ?
O4 N14 1.223(4) . ?
O6 N10 1.222(4) . ?
O7 N15 1.214(4) . ?
O8 N5 1.229(4) . ?
O9 N3 1.222(4) . ?
O10 N3 1.211(4) . ?
O12 N10 1.229(4) . ?
O13 N2 1.216(4) . ?
O14 N5 1.210(4) . ?
N2 N11 1.415(4) . ?
N3 N7 1.411(4) . ?
N5 N12 1.400(4) . ?
N6 N14 1.361(4) . ?
N6 C2 1.456(5) . ?
N6 C8 1.473(4) . ?
N7 C5 1.469(4) . ?
N7 C7 1.465(5) . ?
N9 N10 1.371(4) . ?
N9 C2 1.449(4) . ?
N9 C3 1.478(4) . ?
N11 C7 1.458(5) . ?
N11 C10 1.473(4) . ?
N12 C3 1.433(4) . ?
N12 C5 1.453(4) . ?
N13 N15 1.401(4) . ?
N13 C8 1.438(4) . ?
N13 C10 1.438(4) . ?
C2 H2 1.0000 . ?
C2 C7 1.596(5) . ?
C3 H3 1.0000 . ?
C3 C8 1.574(5) . ?
C5 H5 1.0000 . ?
C5 C10 1.569(5) . ?
C7 H7 1.0000 . ?
C8 H8 1.0000 . ?
C10 H10 1.0000 . ?
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
O5 N8 C4 N1 175.1(3) . . . . ?
O5 N8 C4 C6 -7.5(5) . . . . ?
O11 N8 C4 N1 -5.1(5) . . . . ?
O11 N8 C4 C6 172.3(3) . . . . ?
O15 N4 C1 N16 159.3(3) . . . . ?
O15 N4 C1 C6 -19.7(5) . . . . ?
O16 N4 C1 N16 -20.0(5) . . . . ?
O16 N4 C1 C6 161.0(3) . . . . ?
N1 N16 C1 N4 -179.4(3) . . . . ?
N1 N16 C1 C6 -0.3(4) . . . . ?
N1 C4 C6 Br1 -177.8(2) . . . . ?
N1 C4 C6 C1 -1.1(3) . . . . ?
N4 C1 C6 Br1 -3.3(5) . . . . ?
N4 C1 C6 C4 179.9(3) . . . . ?
N8 C4 C6 Br1 4.5(5) . . . . ?
N8 C4 C6 C1 -178.8(3) . . . . ?
N16 N1 C4 N8 178.9(3) . . . . ?
N16 N1 C4 C6 1.0(4) . . . . ?
N16 C1 C6 Br1 177.6(2) . . . . ?
N16 C1 C6 C4 0.9(4) . . . . ?
C4 N1 N16 C1 -0.5(4) . . . . ?
C9 N1 N16 C1 178.9(3) . . . . ?
C9 N1 C4 N8 -0.3(5) . . . . ?
C9 N1 C4 C6 -178.2(3) . . . . ?
O1 N2 N11 C7 -160.2(3) . . . . ?
O1 N2 N11 C10 -24.8(5) . . . . ?
O8 N5 N12 C3 170.3(3) . . . . ?
O8 N5 N12 C5 11.5(4) . . . . ?
O9 N3 N7 C5 -171.1(3) . . . . ?
O9 N3 N7 C7 -35.4(4) . . . . ?
O10 N3 N7 C5 14.3(4) . . . . ?
O10 N3 N7 C7 150.0(3) . . . . ?
O13 N2 N11 C7 24.6(5) . . . . ?
O13 N2 N11 C10 160.0(3) . . . . ?
O14 N5 N12 C3 -11.4(4) . . . . ?
O14 N5 N12 C5 -170.2(3) . . . . ?
N2 N11 C7 N7 108.3(3) . . . . ?
N2 N11 C7 C2 -138.4(3) . . . . ?
N2 N11 C10 N13 123.2(3) . . . . ?
N2 N11 C10 C5 -120.1(3) . . . . ?
N3 N7 C5 N12 -122.7(3) . . . . ?
N3 N7 C5 C10 121.5(3) . . . . ?
N3 N7 C7 N11 -108.9(3) . . . . ?
N3 N7 C7 C2 137.5(3) . . . . ?
N5 N12 C3 N9 -104.5(3) . . . . ?
N5 N12 C3 C8 144.2(3) . . . . ?
N5 N12 C5 N7 102.2(3) . . . . ?
N5 N12 C5 C10 -144.5(3) . . . . ?
N6 C2 C7 N7 108.6(3) . . . . ?
N6 C2 C7 N11 -2.5(4) . . . . ?
N7 C5 C10 N11 -0.7(3) . . . . ?
N7 C5 C10 N13 117.5(3) . . . . ?
N9 C2 C7 N7 2.1(4) . . . . ?
N9 C2 C7 N11 -109.0(3) . . . . ?
N9 C3 C8 N6 -0.7(3) . . . . ?
N9 C3 C8 N13 -119.1(3) . . . . ?
N10 N9 C2 N6 171.0(3) . . . . ?
N10 N9 C2 C7 -72.0(4) . . . . ?
N10 N9 C3 N12 59.2(4) . . . . ?
N10 N9 C3 C8 174.7(3) . . . . ?
N12 C3 C8 N6 118.8(3) . . . . ?
N12 C3 C8 N13 0.4(3) . . . . ?
N12 C5 C10 N11 -117.4(3) . . . . ?
N12 C5 C10 N13 0.8(4) . . . . ?
N14 N6 C2 N9 -169.3(3) . . . . ?
N14 N6 C2 C7 72.6(4) . . . . ?
N14 N6 C8 N13 -59.5(4) . . . . ?
N14 N6 C8 C3 -175.5(3) . . . . ?
N15 N13 C8 N6 107.1(3) . . . . ?
N15 N13 C8 C3 -141.7(3) . . . . ?
N15 N13 C10 N11 -104.7(3) . . . . ?
N15 N13 C10 C5 141.2(3) . . . . ?
C2 N6 N14 O2 13.6(4) . . . . ?
C2 N6 N14 O4 -168.2(3) . . . . ?
C2 N6 C8 N13 89.3(3) . . . . ?
C2 N6 C8 C3 -26.6(3) . . . . ?
C2 N9 N10 O6 166.3(3) . . . . ?
C2 N9 N10 O12 -15.3(4) . . . . ?
C2 N9 C3 N12 -87.4(3) . . . . ?
C2 N9 C3 C8 28.1(3) . . . . ?
C3 N9 N10 O6 22.2(4) . . . . ?
C3 N9 N10 O12 -159.4(3) . . . . ?
C3 N9 C2 N6 -42.2(3) . . . . ?
C3 N9 C2 C7 74.9(3) . . . . ?
C3 N12 C5 N7 -57.0(4) . . . . ?
C3 N12 C5 C10 56.3(4) . . . . ?
C5 N7 C7 N11 30.5(3) . . . . ?
C5 N7 C7 C2 -83.0(3) . . . . ?
C5 N12 C3 N9 54.6(4) . . . . ?
C5 N12 C3 C8 -56.7(4) . . . . ?
C7 N7 C5 N12 97.4(3) . . . . ?
C7 N7 C5 C10 -18.3(3) . . . . ?
C7 N11 C10 N13 -97.1(3) . . . . ?
C7 N11 C10 C5 19.6(3) . . . . ?
C8 N6 N14 O2 160.0(3) . . . . ?
C8 N6 N14 O4 -21.9(4) . . . . ?
C8 N6 C2 N9 41.7(3) . . . . ?
C8 N6 C2 C7 -76.4(3) . . . . ?
C8 N13 N15 O3 13.1(4) . . . . ?
C8 N13 N15 O7 -168.6(3) . . . . ?
C8 N13 C10 N11 57.3(4) . . . . ?
C8 N13 C10 C5 -56.8(4) . . . . ?
C10 N11 C7 N7 -30.9(3) . . . . ?
C10 N11 C7 C2 82.3(3) . . . . ?
C10 N13 N15 O3 174.6(3) . . . . ?
C10 N13 N15 O7 -7.2(4) . . . . ?
C10 N13 C8 N6 -54.8(4) . . . . ?
C10 N13 C8 C3 56.4(4) . . . . ?
