# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
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data_2211177429-a
_database_code_depnum_ccdc_archive 'CCDC 2302909'
loop_
_audit_author_name
_audit_author_address
'jin zhu'
;North University of China
China
;
_audit_update_record             
;
2023-10-23 deposited with the CCDC.	2023-12-25 downloaded from the CCDC.
;
_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)
;
_shelx_SHELXL_version_number     2019/2
_chemical_name_common            ?
_chemical_name_systematic        ?
_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
_chemical_absolute_configuration rmad
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C N'
_chemical_oxdiff_usercomment     2211177429-A
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   9.21640(10)
_cell_length_b                   12.1632(2)
_cell_length_c                   9.87540(10)
_cell_angle_alpha                90
_cell_angle_beta                 96.5840(10)
_cell_angle_gamma                90
_cell_volume                     1099.74(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    6173
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      76.0840
_cell_measurement_theta_min      3.6310
_shelx_estimated_absorpt_T_max   0.626
_shelx_estimated_absorpt_T_min   0.525
_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_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.081
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             688
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.14
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_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_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_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_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_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_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)'
_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_coef       .
_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_R_factor_all          0.0215
_refine_ls_R_factor_gt           0.0211
_refine_ls_restrained_S_all      1.061
_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
_refine_special_details          ?
_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)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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_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_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) . . . . ?

_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
