# Supplementary Information (SI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2025

####################################################################### 
# 
# 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. 
# 
#######################################################################

data_NB-358-2
_database_code_depnum_ccdc_archive 'CCDC 2430486'
loop_
_audit_author_name
_audit_author_address
'Aida I. Samigullina'
;Zelinsky Institute of Organic Chemistry
Russia
;
_audit_update_record             
;
2025-03-11 deposited with the CCDC.	2025-04-25 downloaded from the CCDC.
;
_audit_creation_date             2024-08-06
_audit_creation_method           
;
Olex2 1.3
(compiled 2019.09.11 svn.r3662 for OlexSys, GUI svn.r5938)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C20 H23 Br N2 O5), C2 H3 N '
_chemical_formula_sum            'C42 H49 Br2 N5 O10'
_chemical_formula_weight         943.68
_chemical_melting_point          ?
_chemical_oxdiff_formula         C21H23BrN3O5
_chemical_oxdiff_usercomment     NB-358-2
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 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           15
_space_group_name_H-M_alt        'I 1 2/a 1'
_space_group_name_Hall           '-I 2ya'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, z'
'-x+1/2, -y+1/2, -z+1/2'
'x, -y+1/2, z+1/2'

_cell_length_a                   12.74413(6)
_cell_length_b                   8.52595(5)
_cell_length_c                   38.0051(2)
_cell_angle_alpha                90
_cell_angle_beta                 90.3633(5)
_cell_angle_gamma                90
_cell_volume                     4129.39(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    21202
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      79.4620
_cell_measurement_theta_min      2.3270
_shelx_estimated_absorpt_T_max   0.816
_shelx_estimated_absorpt_T_min   0.542
_exptl_absorpt_coefficient_mu    3.033
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.473
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.129a (Rigaku Oxford Diffraction, 2024)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
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    1.518
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             1944
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 1 0 0.0995
-1 -1 0 0.0851
1 0 0 0.1182
-1 0 0 0.1049
0 0 -1 0.0422
0 0 1 0.0269
1 -1 1 0.0928
-1 1 -1 0.0740

_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.07
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
0.9996 1.0005 -0.0004 -0.1748 0.0941 0.0888
-0.9996 -1.0005 0.0004 0.1748 -0.0941 -0.0888
0.9995 -0.0000 0.0007 -0.0162 0.0127 0.1191
-0.9995 0.0000 -0.0007 0.0162 -0.0127 -0.1191
0.0000 -0.0004 -0.9999 0.0188 0.0359 -0.0016
-0.0000 0.0004 0.9999 -0.0188 -0.0359 0.0016
0.9993 -1.0001 1.0017 0.1236 -0.1046 0.1509
-0.9993 1.0001 -1.0017 -0.1236 0.1046 -0.1509

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0302
_diffrn_reflns_av_unetI/netI     0.0185
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       48
_diffrn_reflns_limit_l_min       -48
_diffrn_reflns_number            32584
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         80.065
_diffrn_reflns_theta_min         2.325
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(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 0.990
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -51.00 -20.00   0.50    0.32    --  -98.00  45.00   0.00   62
  2  ω    -43.00  39.00   0.50    0.08    --  -40.71  38.00 -30.00  164
  3  ω    -43.00  39.00   0.50    0.08    --  -40.71  38.00 -30.00  164
  4  ω    -27.00  42.00   0.50    0.08    --  -40.71  19.00-180.00  138
  5  ω     61.00 151.00   0.50    0.32    --  119.50-178.00  30.00  180
  6  ω     61.00 151.00   0.50    0.32    --  119.50-178.00  90.00  180
  7  ω     27.00  90.00   0.50    0.08    --   40.71-115.00 108.00  126
  8  ω     45.00 109.00   0.50    0.32    --  119.50-115.00 108.00  128
  9  ω     44.00 108.00   0.50    0.32    --  119.50-111.00 120.00  128
 10  ω     44.00 108.00   0.50    0.32    --  119.50-111.00 150.00  128
 11  ω     58.00 146.00   0.50    0.32    --  119.50-172.00 -33.00  176
 12  ω     41.00 105.00   0.50    0.32    --  119.50 -95.00 120.00  128
 13  ω     61.00 151.00   0.50    0.32    --  119.50-178.00 -60.00  180
 14  ω     61.00 151.00   0.50    0.32    --  119.50-178.00-180.00  180
 15  ω     44.00 108.00   0.50    0.32    --  119.50-111.00-180.00  128
 16  ω     46.00 105.00   0.50    0.32    --  119.50 -77.00-180.00  118
 17  ω     46.00 105.00   0.50    0.32    --  119.50 -77.00 -90.00  118
 18  ω     46.00 105.00   0.50    0.32    --  119.50 -77.00  60.00  118
 19  ω     46.00 105.00   0.50    0.32    --  119.50 -77.00 120.00  118
 20  ω    -42.00  27.00   0.50    0.08    --   40.71 -19.00   0.00  138
 21  ω     87.00 178.00   0.50    0.32    --  119.50  77.00-120.00  182
 22  ω     93.00 178.00   0.50    0.32    --  119.50  61.00 -90.00  170
 23  ω     93.00 178.00   0.50    0.32    --  119.50  61.00 -30.00  170
 24  ω     93.00 178.00   0.50    0.32    --  119.50  45.00   0.00  170
 25  ω     87.00 178.00   0.50    0.32    --  119.50  30.00  90.00  182
 26  ω     87.00 178.00   0.50    0.32    --  119.50  77.00  90.00  182
 27  ω     63.00 123.00   0.50    0.08    --   40.71 178.00 150.00  120
 28  ω     63.00 146.00   0.50    0.32    --  119.50 178.00  60.00  166
 29  ω     63.00 146.00   0.50    0.32    --  119.50 178.00 -90.00  166
 30  ω     66.00 149.00   0.50    0.32    --  119.50 172.00 -20.00  166
 31  ω     63.00 146.00   0.50    0.32    --  119.50 178.00 -60.00  166
 32  ω     63.00 146.00   0.50    0.32    --  119.50 178.00-120.00  166
 33  ω     63.00 146.00   0.50    0.32    --  119.50 178.00-150.00  166
 34  ω    103.00 178.00   0.50    0.32    --  119.50 111.00-150.00  150
 35  ω    101.00 178.00   0.50    0.32    --  119.50 115.00-162.00  154
 36  ω    103.00 178.00   0.50    0.32    --  119.50 111.00 120.00  150
 37  ω    103.00 178.00   0.50    0.32    --  119.50 111.00 150.00  150
 38  ω     -1.00  27.00   0.50    0.08    --   40.71  98.00 110.98   56
 39  ω   -173.00 -80.00   0.50    0.32    --  -98.00-115.00 108.00  186
 40  ω   -121.00 -44.00   0.50    0.08    --  -40.71-172.00 -33.00  154
 41  ω   -119.00 -36.00   0.50    0.32    --  -98.00 172.00 -20.00  166
 42  ω    -83.00  -6.00   0.50    0.08    --  -40.71 115.00-162.00  154
;
_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      -0.0162299000
_diffrn_orient_matrix_UB_12      -0.1584927000
_diffrn_orient_matrix_UB_13      -0.0187138000
_diffrn_orient_matrix_UB_21      0.0127228000
_diffrn_orient_matrix_UB_22      0.0813232000
_diffrn_orient_matrix_UB_23      -0.0359172000
_diffrn_orient_matrix_UB_31      0.1191325000
_diffrn_orient_matrix_UB_32      -0.0302656000
_diffrn_orient_matrix_UB_33      0.0015732000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4342
_reflns_number_total             4467
_reflns_odcompleteness_completeness 98.05
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     80.95
_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 1.171.43.129a (Rigaku OD, 2024)'
_computing_data_collection       
'CrysAlisPro system (CCD 43.129a 64-bit (release 29-06-2024))'
_computing_data_reduction        'CrysAlisPro 1.171.43.129a (Rigaku OD, 2024)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.354
_refine_diff_density_min         -0.334
_refine_diff_density_rms         0.056
_refine_ls_extinction_coef       0.00022(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     292
_refine_ls_number_reflns         4467
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0256
_refine_ls_R_factor_gt           0.0248
_refine_ls_restrained_S_all      1.054
_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)+(0.0312P)²+5.0658P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0632
_refine_ls_wR_factor_ref         0.0638
_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. Others
 Fixed Sof: C27(0.5) H27A(0.5) H27B(0.5) H27C(0.5) N25(0.5) C26(0.5)
3.a Aromatic/amide H refined with riding coordinates:
 C14(H14), C15(H15), C17(H17), C18(H18)
3.b Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C), C20(H20A,H20B,H20C), C21(H21A,H21B,H21C), C22(H22A,H22B,
 H22C), C23(H23A,H23B,H23C), C24(H24A,H24B,H24C), C27(H27A,H27B,H27C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
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 0.46457(2) 0.75428(2) 0.24372(2) 0.01789(7) Uani 1 1 d . . . . .
O1 O 0.12403(7) 0.58817(11) 0.41362(2) 0.01500(19) Uani 1 1 d . . . . .
O3 O 0.25698(7) 0.50503(11) 0.45269(2) 0.01427(19) Uani 1 1 d . . . . .
O4 O 0.37772(7) 0.33408(12) 0.43709(3) 0.01624(19) Uani 1 1 d . . . . .
O6 O 0.10993(8) 0.49316(12) 0.35982(3) 0.0177(2) Uani 1 1 d . . . . .
O12 O 0.15762(7) 0.19316(12) 0.32124(3) 0.01685(19) Uani 1 1 d . . . . .
N7 N 0.30135(8) 0.11942(13) 0.37899(3) 0.0127(2) Uani 1 1 d . . . . .
N8 N 0.32835(9) 0.04933(14) 0.41159(3) 0.0150(2) Uani 1 1 d . . . . .
C2 C 0.14818(10) 0.55082(16) 0.44975(3) 0.0144(2) Uani 1 1 d . . . . .
C4 C 0.29329(10) 0.39482(15) 0.42960(3) 0.0127(2) Uani 1 1 d . . . . .
C5 C 0.23265(10) 0.37024(15) 0.39815(3) 0.0124(2) Uani 1 1 d . . . . .
C6 C 0.15214(10) 0.48273(15) 0.38854(3) 0.0132(2) Uani 1 1 d . . . . .
C9 C 0.40093(10) -0.06338(16) 0.39310(4) 0.0155(3) Uani 1 1 d . . . . .
C10 C 0.34376(10) -0.01721(15) 0.35772(3) 0.0146(2) Uani 1 1 d . . . . .
C11 C 0.25713(10) 0.25392(14) 0.37254(3) 0.0118(2) Uani 1 1 d . . . . .
C12 C 0.22500(10) 0.27708(16) 0.33381(3) 0.0129(2) Uani 1 1 d . . . . .
C13 C 0.28426(10) 0.39473(15) 0.31309(3) 0.0132(2) Uani 1 1 d . . . . .
C14 C 0.24455(10) 0.43776(17) 0.28008(3) 0.0164(3) Uani 1 1 d . . . . .
H14 H 0.180785 0.393093 0.271742 0.020 Uiso 1 1 calc R U . . .
C15 C 0.29775(11) 0.54512(17) 0.25951(3) 0.0175(3) Uani 1 1 d . . . . .
H15 H 0.270483 0.575900 0.237235 0.021 Uiso 1 1 calc R U . . .
C16 C 0.39173(10) 0.60715(15) 0.27198(3) 0.0143(2) Uani 1 1 d . . . . .
C17 C 0.43383(10) 0.56470(16) 0.30441(3) 0.0146(2) Uani 1 1 d . . . . .
H17 H 0.498706 0.607287 0.312311 0.018 Uiso 1 1 calc R U . . .
C18 C 0.37881(10) 0.45836(16) 0.32506(3) 0.0137(2) Uani 1 1 d . . . . .
H18 H 0.405818 0.428902 0.347456 0.016 Uiso 1 1 calc R U . . .
C19 C 0.13635(11) 0.70268(18) 0.46965(4) 0.0201(3) Uani 1 1 d . . . . .
H19A H 0.185033 0.780740 0.460177 0.030 Uiso 1 1 calc R U . . .
H19B H 0.152128 0.685057 0.494612 0.030 Uiso 1 1 calc R U . . .
H19C H 0.064193 0.740976 0.467107 0.030 Uiso 1 1 calc R U . . .
C20 C 0.07815(10) 0.42137(17) 0.46333(4) 0.0174(3) Uani 1 1 d . . . . .
H20A H 0.004505 0.452342 0.460546 0.026 Uiso 1 1 calc R U . . .
H20B H 0.093507 0.402824 0.488286 0.026 Uiso 1 1 calc R U . . .
H20C H 0.091040 0.325067 0.449965 0.026 Uiso 1 1 calc R U . . .
C21 C 0.38895(13) -0.23017(17) 0.40608(4) 0.0219(3) Uani 1 1 d . . . . .
H21A H 0.410345 -0.236037 0.430860 0.033 Uiso 1 1 calc R U . . .
H21B H 0.433287 -0.299922 0.392069 0.033 Uiso 1 1 calc R U . . .
H21C H 0.315458 -0.262559 0.403726 0.033 Uiso 1 1 calc R U . . .
C22 C 0.51472(11) -0.00852(18) 0.39562(4) 0.0217(3) Uani 1 1 d . . . . .
H22A H 0.518681 0.103108 0.389626 0.033 Uiso 1 1 calc R U . . .
H22B H 0.557704 -0.069033 0.379194 0.033 Uiso 1 1 calc R U . . .
H22C H 0.540843 -0.024405 0.419667 0.033 Uiso 1 1 calc R U . . .
C23 C 0.25502(11) -0.12772(17) 0.34692(4) 0.0188(3) Uani 1 1 d . . . . .
H23A H 0.209808 -0.147539 0.367204 0.028 Uiso 1 1 calc R U . . .
H23B H 0.284662 -0.227042 0.338641 0.028 Uiso 1 1 calc R U . . .
H23C H 0.213608 -0.079529 0.327986 0.028 Uiso 1 1 calc R U . . .
C24 C 0.41165(11) 0.02858(18) 0.32676(4) 0.0201(3) Uani 1 1 d . . . . .
H24A H 0.366819 0.062953 0.307186 0.030 Uiso 1 1 calc R U . . .
H24B H 0.453436 -0.061976 0.319373 0.030 Uiso 1 1 calc R U . . .
H24C H 0.458584 0.114358 0.333712 0.030 Uiso 1 1 calc R U . . .
C27 C 0.239(2) 1.0989(4) 0.5010(7) 0.036(3) Uani 0.5 1 d . . P A -1
H27A H 0.271064 1.040977 0.481508 0.054 Uiso 0.5 1 calc R U P A -1
H27B H 0.276844 1.074663 0.522900 0.054 Uiso 0.5 1 calc R U P A -1
H27C H 0.243593 1.211733 0.496310 0.054 Uiso 0.5 1 calc R U P A -1
N25 N 0.0439(3) 1.0149(4) 0.50707(11) 0.0475(9) Uani 0.5 1 d . . P A -1
C26 C 0.1293(3) 1.0532(4) 0.50436(9) 0.0308(7) Uani 0.5 1 d . . P A -1
H8 H 0.3607(15) 0.122(2) 0.4250(5) 0.021(5) Uiso 1 1 d . . . . .


_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 C16 1.8978(13) . ?
O1 C2 1.4410(15) . ?
O1 C6 1.3598(16) . ?
O3 C2 1.4442(15) . ?
O3 C4 1.3684(16) . ?
O4 C4 1.2260(17) . ?
O6 C6 1.2173(17) . ?
O12 C12 1.2136(17) . ?
N7 N8 1.4159(15) . ?
N7 C10 1.5193(16) . ?
N7 C11 1.3004(17) . ?
N8 C9 1.5103(17) . ?
N8 H8 0.90(2) . ?
C2 C19 1.5075(19) . ?
C2 C20 1.5122(19) . ?
C4 C5 1.4345(17) . ?
C5 C6 1.4496(17) . ?
C5 C11 1.4255(18) . ?
C9 C10 1.5751(18) . ?
C9 C21 1.5133(19) . ?
C9 C22 1.5262(19) . ?
C10 C23 1.5262(19) . ?
C10 C24 1.5160(18) . ?
C11 C12 1.5380(18) . ?
C12 C13 1.4848(18) . ?
C13 C14 1.3987(18) . ?
C13 C18 1.3952(18) . ?
C14 H14 0.9500 . ?
C14 C15 1.384(2) . ?
C15 H15 0.9500 . ?
C15 C16 1.3898(19) . ?
C16 C17 1.3891(18) . ?
C17 H17 0.9500 . ?
C17 C18 1.3915(19) . ?
C18 H18 0.9500 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
C27 C26 1.46(3) . ?
N25 C26 1.142(5) . ?

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
C6 O1 C2 117.79(10) . . ?
C4 O3 C2 117.68(10) . . ?
N8 N7 C10 93.25(9) . . ?
C11 N7 N8 129.77(11) . . ?
C11 N7 C10 136.98(11) . . ?
N7 N8 C9 90.44(9) . . ?
N7 N8 H8 108.2(13) . . ?
C9 N8 H8 115.0(12) . . ?
O1 C2 O3 109.42(10) . . ?
O1 C2 C19 105.48(11) . . ?
O1 C2 C20 111.32(10) . . ?
O3 C2 C19 107.00(10) . . ?
O3 C2 C20 110.17(11) . . ?
C19 C2 C20 113.24(11) . . ?
O3 C4 C5 116.88(11) . . ?
O4 C4 O3 116.16(11) . . ?
O4 C4 C5 126.81(12) . . ?
C4 C5 C6 119.34(11) . . ?
C11 C5 C4 123.46(12) . . ?
C11 C5 C6 116.49(11) . . ?
O1 C6 C5 116.75(11) . . ?
O6 C6 O1 117.61(12) . . ?
O6 C6 C5 125.61(12) . . ?
N8 C9 C10 87.53(9) . . ?
N8 C9 C21 112.51(11) . . ?
N8 C9 C22 111.11(11) . . ?
C21 C9 C10 117.79(12) . . ?
C21 C9 C22 111.42(12) . . ?
C22 C9 C10 114.29(11) . . ?
N7 C10 C9 84.35(9) . . ?
N7 C10 C23 110.54(10) . . ?
C23 C10 C9 114.41(11) . . ?
C24 C10 N7 114.98(11) . . ?
C24 C10 C9 117.62(11) . . ?
C24 C10 C23 112.08(12) . . ?
N7 C11 C5 125.54(12) . . ?
N7 C11 C12 113.96(11) . . ?
C5 C11 C12 120.40(11) . . ?
O12 C12 C11 119.00(12) . . ?
O12 C12 C13 123.39(12) . . ?
C13 C12 C11 117.47(11) . . ?
C14 C13 C12 118.08(12) . . ?
C18 C13 C12 122.06(12) . . ?
C18 C13 C14 119.82(12) . . ?
C13 C14 H14 119.9 . . ?
C15 C14 C13 120.29(12) . . ?
C15 C14 H14 119.9 . . ?
C14 C15 H15 120.6 . . ?
C14 C15 C16 118.90(12) . . ?
C16 C15 H15 120.6 . . ?
C15 C16 Br1 118.82(10) . . ?
C17 C16 Br1 119.14(10) . . ?
C17 C16 C15 122.04(12) . . ?
C16 C17 H17 120.8 . . ?
C16 C17 C18 118.49(12) . . ?
C18 C17 H17 120.8 . . ?
C13 C18 H18 119.8 . . ?
C17 C18 C13 120.44(12) . . ?
C17 C18 H18 119.8 . . ?
C2 C19 H19A 109.5 . . ?
C2 C19 H19B 109.5 . . ?
C2 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C2 C20 H20A 109.5 . . ?
C2 C20 H20B 109.5 . . ?
C2 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C9 C21 H21A 109.5 . . ?
C9 C21 H21B 109.5 . . ?
C9 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C9 C22 H22A 109.5 . . ?
C9 C22 H22B 109.5 . . ?
C9 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C10 C23 H23A 109.5 . . ?
C10 C23 H23B 109.5 . . ?
C10 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C10 C24 H24A 109.5 . . ?
C10 C24 H24B 109.5 . . ?
C10 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
H27A C27 H27B 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C26 C27 H27A 109.5 . . ?
C26 C27 H27B 109.5 . . ?
C26 C27 H27C 109.5 . . ?
N25 C26 C27 178.9(5) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N8 H8 O4 0.90(2) 1.88(2) 2.6873(16) 148.6(18) . yes

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
Br1 C16 C17 C18 179.12(10) . . . . ?
O3 C4 C5 C6 13.53(17) . . . . ?
O3 C4 C5 C11 -176.51(11) . . . . ?
O4 C4 C5 C6 -161.84(13) . . . . ?
O4 C4 C5 C11 8.1(2) . . . . ?
O12 C12 C13 C14 15.8(2) . . . . ?
O12 C12 C13 C18 -162.05(13) . . . . ?
N7 N8 C9 C10 -15.96(10) . . . . ?
N7 N8 C9 C21 -135.12(12) . . . . ?
N7 N8 C9 C22 99.16(12) . . . . ?
N7 C11 C12 O12 64.99(16) . . . . ?
N7 C11 C12 C13 -110.75(13) . . . . ?
N8 N7 C10 C9 -15.95(9) . . . . ?
N8 N7 C10 C23 98.02(11) . . . . ?
N8 N7 C10 C24 -133.86(12) . . . . ?
N8 N7 C11 C5 5.4(2) . . . . ?
N8 N7 C11 C12 -170.88(12) . . . . ?
N8 C9 C10 N7 14.92(9) . . . . ?
N8 C9 C10 C23 -95.10(12) . . . . ?
N8 C9 C10 C24 130.21(12) . . . . ?
C2 O1 C6 O6 161.93(12) . . . . ?
C2 O1 C6 C5 -19.95(16) . . . . ?
C2 O3 C4 O4 -165.11(11) . . . . ?
C2 O3 C4 C5 19.02(16) . . . . ?
C4 O3 C2 O1 -49.46(15) . . . . ?
C4 O3 C2 C19 -163.27(11) . . . . ?
C4 O3 C2 C20 73.23(14) . . . . ?
C4 C5 C6 O1 -13.14(17) . . . . ?
C4 C5 C6 O6 164.81(13) . . . . ?
C4 C5 C11 N7 31.4(2) . . . . ?
C4 C5 C11 C12 -152.52(12) . . . . ?
C5 C11 C12 O12 -111.50(14) . . . . ?
C5 C11 C12 C13 72.76(16) . . . . ?
C6 O1 C2 O3 49.97(15) . . . . ?
C6 O1 C2 C19 164.76(11) . . . . ?
C6 O1 C2 C20 -72.04(14) . . . . ?
C6 C5 C11 N7 -158.35(13) . . . . ?
C6 C5 C11 C12 17.71(17) . . . . ?
C10 N7 N8 C9 16.58(10) . . . . ?
C10 N7 C11 C5 -173.78(13) . . . . ?
C10 N7 C11 C12 9.9(2) . . . . ?
C11 N7 N8 C9 -162.87(13) . . . . ?
C11 N7 C10 C9 163.42(15) . . . . ?
C11 N7 C10 C23 -82.61(18) . . . . ?
C11 N7 C10 C24 45.5(2) . . . . ?
C11 C5 C6 O1 176.20(11) . . . . ?
C11 C5 C6 O6 -5.8(2) . . . . ?
C11 C12 C13 C14 -168.65(12) . . . . ?
C11 C12 C13 C18 13.49(18) . . . . ?
C12 C13 C14 C15 -178.99(12) . . . . ?
C12 C13 C18 C17 177.97(12) . . . . ?
C13 C14 C15 C16 1.0(2) . . . . ?
C14 C13 C18 C17 0.1(2) . . . . ?
C14 C15 C16 Br1 179.97(10) . . . . ?
C14 C15 C16 C17 0.0(2) . . . . ?
C15 C16 C17 C18 -0.9(2) . . . . ?
C16 C17 C18 C13 0.84(19) . . . . ?
C18 C13 C14 C15 -1.1(2) . . . . ?
C21 C9 C10 N7 129.15(12) . . . . ?
C21 C9 C10 C23 19.13(17) . . . . ?
C21 C9 C10 C24 -115.56(14) . . . . ?
C22 C9 C10 N7 -97.16(12) . . . . ?
C22 C9 C10 C23 152.82(12) . . . . ?
C22 C9 C10 C24 18.12(17) . . . . ?

_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 1.190
_oxdiff_exptl_absorpt_empirical_full_min 0.871
