# Supplementary Information (SI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2026

####################################################################### 
# 
# 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_yasui-377_auto
_database_code_depnum_ccdc_archive 'CCDC 2443840'
loop_
_audit_author_name
_audit_author_address
'Masato Morita'
;Kyoto Institute of Technology
Japan
;
_audit_update_record             
;
2025-04-15 deposited with the CCDC.	2026-02-20 downloaded from the CCDC.
;
_audit_creation_date             2025-04-01
_audit_creation_method           
;
Olex2 1.5
(compiled 2025.03.06 svn.red2d20d0 for OlexSys, GUI svn.r7188)
;
_shelx_SHELXL_version_number     2019/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H15 Br N2 O6'
_chemical_formula_sum            'C14 H15 Br N2 O6'
_chemical_formula_weight         387.19
_chemical_melting_point          ?
_chemical_oxdiff_formula         C14H15BrN2O6
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   25.6781(10)
_cell_length_b                   11.8274(4)
_cell_length_c                   22.4137(9)
_cell_angle_alpha                90
_cell_angle_beta                 115.471(5)
_cell_angle_gamma                90
_cell_volume                     6145.5(5)
_cell_formula_units_Z            16
_cell_measurement_reflns_used    11241
_cell_measurement_temperature    173
_cell_measurement_theta_max      29.0220
_cell_measurement_theta_min      3.2040
_cell_oxdiff_angle_alpha         90.0054(18)
_cell_oxdiff_angle_beta          115.471(2)
_cell_oxdiff_angle_gamma         89.9642(18)
_cell_oxdiff_length_a            25.6818(6)
_cell_oxdiff_length_b            11.8223(2)
_cell_oxdiff_length_c            22.4201(5)
_cell_oxdiff_measurement_reflns_used 11221
_cell_oxdiff_volume              6145.5(2)
_shelx_estimated_absorpt_T_max   0.539
_shelx_estimated_absorpt_T_min   0.369
_exptl_absorpt_coefficient_mu    2.709
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.50737
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.117a (Rigaku Oxford Diffraction, 2021)
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    1.674
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             3136
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-33 6 9 0.2019
-1 1 29 0.1705
31 -6 0 0.2029
3 -1 -30 0.1168
-33 4 22 0.2552
16 15 -7 0.0796
18 -14 -14 0.1743
-12 -16 4 0.1535
24 -9 5 0.1942

_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.26
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
-33.0940 6.4108 8.7949 0.3543 -0.2579 0.8988
-1.1514 0.5863 28.9366 -0.7541 0.5488 0.3608
30.7849 -5.8648 -0.4013 -0.5379 0.3915 -0.7466
2.9599 -0.9377 -29.5068 0.7371 -0.5365 -0.4109
-33.3282 3.7433 21.6284 0.0933 0.1283 0.9873
15.8986 14.9660 -7.0497 -0.5875 -0.8072 -0.0565
18.4903 -13.6733 -14.2614 0.3241 0.4452 -0.8347
-11.6370 -15.7865 4.2175 0.5867 0.8060 -0.0782
24.4057 -8.9442 5.3073 -0.4580 0.6315 -0.6256

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0314
_diffrn_reflns_av_unetI/netI     0.0324
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       33
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            22990
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.483
_diffrn_reflns_theta_min         3.052
_diffrn_ambient_temperature      173
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -81.00 -55.00   0.50    1.15    --  -13.20  18.00-180.00   52
  2  ω    -72.00  30.00   0.50    1.15    --  -13.20  46.00-150.00  204
  3  ω     51.00  76.00   0.50    1.15    --  -13.20  46.00-150.00   50
  4  ω   -103.00  68.00   0.50    1.15    --  -13.20  46.00-180.00  342
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC10 (RCD3): quarter-chi single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0230100000
_diffrn_orient_matrix_UB_12      -0.0272595000
_diffrn_orient_matrix_UB_13      -0.0264233000
_diffrn_orient_matrix_UB_21      0.0037490000
_diffrn_orient_matrix_UB_22      -0.0484539000
_diffrn_orient_matrix_UB_23      0.0200972000
_diffrn_orient_matrix_UB_31      -0.0198085000
_diffrn_orient_matrix_UB_32      0.0225547000
_diffrn_orient_matrix_UB_33      0.0112221000
_diffrn_oxdiff_digest_hkl        
;
01e0f28d397ef79d97bbae1a69caf7f98f9080
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Rotating-anode X-ray tube (dual wavelength)'
_diffrn_source_type              'Rigaku (Mo) X-ray DW Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5875
_reflns_number_total             7044
_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 1.171.41.117a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.117a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.117a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.333
_refine_diff_density_min         -0.276
_refine_diff_density_rms         0.058
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     423
_refine_ls_number_reflns         7044
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0388
_refine_ls_R_factor_gt           0.0279
_refine_ls_restrained_S_all      1.026
_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)+(0.0280P)²+6.3093P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0641
_refine_ls_wR_factor_ref         0.0671
_refine_special_details          ?
_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 Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C34(H34A,H34B)
2.b Aromatic/amide H refined with riding coordinates:
 C24(H24), C1(H1)
2.c Idealised Me refined as rotating group:
 C46(H46A,H46B,H46C), C23(H23A,H23B,H23C), C43(H43A,H43B,H43C), C22(H22A,H22B,
 H22C), C39(H39A,H39B,H39C), C35(H35A,H35B,H35C), C18(H18A,H18B,H18C), C14(H14A,
 H14B,H14C)
;
_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
Br45 Br 0.14465(2) 0.31779(2) -0.15273(2) 0.02905(6) Uani 1 1 d . . . . .
Br6 Br 0.17519(2) 0.63545(2) 0.20729(2) 0.03235(6) Uani 1 1 d . . . . .
O42 O 0.22499(6) 0.54009(11) -0.11212(6) 0.0267(3) Uani 1 1 d . . . . .
O41 O 0.30281(6) 0.62235(12) -0.03315(7) 0.0311(3) Uani 1 1 d . . . . .
O38 O 0.38111(6) 0.53138(12) 0.11574(7) 0.0311(3) Uani 1 1 d . . . . .
O17 O -0.03484(5) 0.24015(11) -0.00581(7) 0.0295(3) Uani 1 1 d . . . . .
O20 O 0.03490(6) 0.28162(12) 0.14518(7) 0.0320(3) Uani 1 1 d . . . . .
O21 O 0.09163(6) 0.42580(12) 0.20239(6) 0.0298(3) Uani 1 1 d . . . . .
O33 O 0.31868(6) 0.47765(13) 0.20211(7) 0.0339(3) Uani 1 1 d . . . . .
O12 O 0.01255(6) 0.30560(12) -0.10511(7) 0.0336(3) Uani 1 1 d . . . . .
O32 O 0.24309(7) 0.36837(13) 0.18912(7) 0.0378(4) Uani 1 1 d . . . . .
O37 O 0.32232(6) 0.67350(12) 0.11342(8) 0.0339(3) Uani 1 1 d . . . . .
O16 O 0.05031(6) 0.15562(11) 0.02262(8) 0.0345(3) Uani 1 1 d . . . . .
O11 O 0.03765(7) 0.47796(13) -0.12536(7) 0.0383(4) Uani 1 1 d . . . . .
N26 N 0.21841(6) 0.35881(13) 0.04598(8) 0.0213(3) Uani 1 1 d . . . . .
N3 N 0.09347(6) 0.50918(12) 0.02124(7) 0.0206(3) Uani 1 1 d . . . . .
N2 N 0.12763(7) 0.59141(13) 0.01306(8) 0.0246(3) Uani 1 1 d . . . . .
N25 N 0.18374(6) 0.26743(13) 0.03949(8) 0.0247(3) Uani 1 1 d . . . . .
C27 C 0.21310(7) 0.39393(16) -0.01469(9) 0.0208(4) Uani 1 1 d . . . . .
C4 C 0.10342(7) 0.50215(15) 0.08640(9) 0.0205(4) Uani 1 1 d . . . . .
C40 C 0.26350(8) 0.55496(16) -0.04937(9) 0.0219(4) Uani 1 1 d . . . . .
C28 C 0.25312(8) 0.48261(16) -0.00327(9) 0.0220(4) Uani 1 1 d . . . . .
C30 C 0.26131(8) 0.41935(15) 0.09725(9) 0.0219(4) Uani 1 1 d . . . . .
C29 C 0.28271(8) 0.49462(15) 0.06565(9) 0.0217(4) Uani 1 1 d . . . . .
C31 C 0.27187(8) 0.41566(16) 0.16624(9) 0.0257(4) Uani 1 1 d . . . . .
C24 C 0.15629(8) 0.24459(16) -0.02581(10) 0.0250(4) Uani 1 1 d . . . . .
H24 H 0.129653 0.184474 -0.044521 0.030 Uiso 1 1 calc R U . . .
C5 C 0.14313(8) 0.58983(16) 0.11902(9) 0.0238(4) Uani 1 1 d . . . . .
C19 C 0.06433(8) 0.36299(16) 0.14780(9) 0.0235(4) Uani 1 1 d . . . . .
C44 C 0.17209(8) 0.31968(16) -0.06114(9) 0.0232(4) Uani 1 1 d . . . . .
C8 C 0.04864(7) 0.35462(15) 0.02917(9) 0.0216(4) Uani 1 1 d . . . . .
C7 C 0.07379(7) 0.40506(16) 0.09216(9) 0.0217(4) Uani 1 1 d . . . . .
C1 C 0.15606(8) 0.64121(16) 0.07283(10) 0.0263(4) Uani 1 1 d . . . . .
H1 H 0.181585 0.703581 0.081327 0.032 Uiso 1 1 calc R U . . .
C9 C 0.06021(8) 0.41866(15) -0.01564(9) 0.0219(4) Uani 1 1 d . . . . .
C10 C 0.03686(8) 0.40788(17) -0.08675(9) 0.0254(4) Uani 1 1 d . . . . .
C15 C 0.02204(8) 0.23946(16) 0.01522(9) 0.0236(4) Uani 1 1 d . . . . .
C36 C 0.32965(8) 0.57854(17) 0.10085(9) 0.0248(4) Uani 1 1 d . . . . .
C46 C 0.18639(8) 0.19559(17) 0.09349(10) 0.0284(4) Uani 1 1 d . . . . .
H46A H 0.226223 0.170574 0.119448 0.043 Uiso 1 1 calc R U . . .
H46B H 0.161492 0.129526 0.075460 0.043 Uiso 1 1 calc R U . . .
H46C H 0.173239 0.238328 0.121918 0.043 Uiso 1 1 calc R U . . .
C23 C 0.12185(9) 0.63684(18) -0.04950(10) 0.0314(5) Uani 1 1 d . . . . .
H23A H 0.130252 0.577447 -0.074582 0.047 Uiso 1 1 calc R U . . .
H23B H 0.149029 0.699511 -0.041417 0.047 Uiso 1 1 calc R U . . .
H23C H 0.082376 0.664303 -0.074820 0.047 Uiso 1 1 calc R U . . .
C43 C 0.23258(9) 0.61097(18) -0.16046(10) 0.0300(4) Uani 1 1 d . . . . .
H43A H 0.207875 0.583423 -0.204999 0.045 Uiso 1 1 calc R U . . .
H43B H 0.273002 0.608473 -0.153268 0.045 Uiso 1 1 calc R U . . .
H43C H 0.221992 0.688993 -0.155837 0.045 Uiso 1 1 calc R U . . .
C13 C -0.01661(9) 0.2862(2) -0.17543(10) 0.0371(5) Uani 1 1 d . . . . .
H13A H 0.009506 0.303081 -0.196345 0.045 Uiso 1 1 calc R U . . .
H13B H -0.050975 0.335491 -0.195557 0.045 Uiso 1 1 calc R U . . .
C34 C 0.33071(9) 0.4947(2) 0.27075(10) 0.0355(5) Uani 1 1 d . . . . .
H34A H 0.344404 0.423458 0.295868 0.043 Uiso 1 1 calc R U . . .
H34B H 0.295434 0.519546 0.274522 0.043 Uiso 1 1 calc R U . . .
C22 C 0.07950(10) 0.3965(2) 0.25746(11) 0.0407(5) Uani 1 1 d . . . . .
H22A H 0.037730 0.398323 0.243568 0.061 Uiso 1 1 calc R U . . .
H22B H 0.098343 0.450949 0.293344 0.061 Uiso 1 1 calc R U . . .
H22C H 0.094153 0.320425 0.272969 0.061 Uiso 1 1 calc R U . . .
C39 C 0.43056(9) 0.6022(2) 0.15276(12) 0.0429(6) Uani 1 1 d . . . . .
H39A H 0.431832 0.664867 0.124808 0.064 Uiso 1 1 calc R U . . .
H39B H 0.465927 0.557281 0.166734 0.064 Uiso 1 1 calc R U . . .
H39C H 0.427395 0.632388 0.191782 0.064 Uiso 1 1 calc R U . . .
C35 C 0.37627(11) 0.5835(2) 0.29717(11) 0.0435(6) Uani 1 1 d . . . . .
H35A H 0.361119 0.655074 0.274259 0.065 Uiso 1 1 calc R U . . .
H35B H 0.409805 0.560424 0.290012 0.065 Uiso 1 1 calc R U . . .
H35C H 0.387816 0.593248 0.344606 0.065 Uiso 1 1 calc R U . . .
C18 C -0.06080(10) 0.12843(19) -0.01841(14) 0.0446(6) Uani 1 1 d . . . . .
H18A H -0.054543 0.092250 -0.054120 0.067 Uiso 1 1 calc R U . . .
H18B H -0.102308 0.135181 -0.031349 0.067 Uiso 1 1 calc R U . . .
H18C H -0.043085 0.082462 0.021745 0.067 Uiso 1 1 calc R U . . .
C14 C -0.03383(19) 0.1670(3) -0.18519(15) 0.0852(12) Uani 1 1 d . . . . .
H14A H -0.055734 0.151893 -0.232516 0.128 Uiso 1 1 calc R U . . .
H14B H -0.057941 0.150365 -0.162245 0.128 Uiso 1 1 calc R U . . .
H14C H 0.000651 0.119135 -0.167345 0.128 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
Br45 C44 1.8620(19) . ?
Br6 C5 1.8660(19) . ?
O42 C40 1.338(2) . ?
O42 C43 1.448(2) . ?
O41 C40 1.213(2) . ?
O38 C36 1.338(2) . ?
O38 C39 1.448(2) . ?
O17 C15 1.328(2) . ?
O17 C18 1.452(2) . ?
O20 C19 1.209(2) . ?
O21 C19 1.343(2) . ?
O21 C22 1.439(2) . ?
O33 C31 1.341(2) . ?
O33 C34 1.447(2) . ?
O12 C10 1.342(2) . ?
O12 C13 1.443(2) . ?
O32 C31 1.203(2) . ?
O37 C36 1.192(2) . ?
O16 C15 1.198(2) . ?
O11 C10 1.205(2) . ?
N26 N25 1.368(2) . ?
N26 C27 1.371(2) . ?
N26 C30 1.399(2) . ?
N3 N2 1.374(2) . ?
N3 C4 1.373(2) . ?
N3 C9 1.397(2) . ?
N2 C1 1.354(2) . ?
N2 C23 1.448(2) . ?
N25 C24 1.351(2) . ?
N25 C46 1.456(2) . ?
C27 C28 1.413(3) . ?
C27 C44 1.422(3) . ?
C4 C5 1.417(3) . ?
C4 C7 1.414(3) . ?
C40 C28 1.452(3) . ?
C28 C29 1.405(3) . ?
C30 C29 1.390(3) . ?
C30 C31 1.451(3) . ?
C29 C36 1.497(3) . ?
C24 H24 0.9500 . ?
C24 C44 1.363(3) . ?
C5 C1 1.359(3) . ?
C19 C7 1.457(3) . ?
C8 C7 1.408(3) . ?
C8 C9 1.388(3) . ?
C8 C15 1.495(3) . ?
C1 H1 0.9500 . ?
C9 C10 1.447(3) . ?
C46 H46A 0.9800 . ?
C46 H46B 0.9800 . ?
C46 H46C 0.9800 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C43 H43A 0.9800 . ?
C43 H43B 0.9800 . ?
C43 H43C 0.9800 . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C13 C14 1.465(4) . ?
C34 H34A 0.9900 . ?
C34 H34B 0.9900 . ?
C34 C35 1.492(3) . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C39 H39A 0.9800 . ?
C39 H39B 0.9800 . ?
C39 H39C 0.9800 . ?
C35 H35A 0.9800 . ?
C35 H35B 0.9800 . ?
C35 H35C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?

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
C40 O42 C43 115.72(15) . . ?
C36 O38 C39 115.50(16) . . ?
C15 O17 C18 113.97(16) . . ?
C19 O21 C22 115.32(16) . . ?
C31 O33 C34 116.12(15) . . ?
C10 O12 C13 115.65(16) . . ?
N25 N26 C27 110.56(15) . . ?
N25 N26 C30 137.59(16) . . ?
C27 N26 C30 111.52(15) . . ?
N2 N3 C9 136.61(16) . . ?
C4 N3 N2 110.33(14) . . ?
C4 N3 C9 111.70(15) . . ?
N3 N2 C23 125.90(16) . . ?
C1 N2 N3 106.24(15) . . ?
C1 N2 C23 125.70(17) . . ?
N26 N25 C46 125.24(15) . . ?
C24 N25 N26 106.60(15) . . ?
C24 N25 C46 126.87(16) . . ?
N26 C27 C28 106.91(15) . . ?
N26 C27 C44 105.41(16) . . ?
C28 C27 C44 147.49(18) . . ?
N3 C4 C5 105.55(16) . . ?
N3 C4 C7 106.57(15) . . ?
C7 C4 C5 147.48(18) . . ?
O42 C40 C28 113.05(16) . . ?
O41 C40 O42 123.03(17) . . ?
O41 C40 C28 123.91(17) . . ?
C27 C28 C40 130.59(17) . . ?
C29 C28 C27 106.35(16) . . ?
C29 C28 C40 123.01(17) . . ?
N26 C30 C31 125.45(16) . . ?
C29 C30 N26 104.68(16) . . ?
C29 C30 C31 128.96(17) . . ?
C28 C29 C36 125.34(16) . . ?
C30 C29 C28 110.50(16) . . ?
C30 C29 C36 124.14(16) . . ?
O33 C31 C30 109.34(16) . . ?
O32 C31 O33 123.71(18) . . ?
O32 C31 C30 126.91(18) . . ?
N25 C24 H24 124.7 . . ?
N25 C24 C44 110.63(17) . . ?
C44 C24 H24 124.7 . . ?
C4 C5 Br6 130.55(15) . . ?
C1 C5 Br6 122.51(15) . . ?
C1 C5 C4 106.94(17) . . ?
O20 C19 O21 123.72(18) . . ?
O20 C19 C7 124.13(18) . . ?
O21 C19 C7 112.15(16) . . ?
C27 C44 Br45 128.67(14) . . ?
C24 C44 Br45 124.53(14) . . ?
C24 C44 C27 106.79(17) . . ?
C7 C8 C15 124.54(17) . . ?
C9 C8 C7 110.23(16) . . ?
C9 C8 C15 124.50(17) . . ?
C4 C7 C19 130.55(17) . . ?
C8 C7 C4 106.58(16) . . ?
C8 C7 C19 122.70(17) . . ?
N2 C1 C5 110.77(17) . . ?
N2 C1 H1 124.6 . . ?
C5 C1 H1 124.6 . . ?
N3 C9 C10 125.27(17) . . ?
C8 C9 N3 104.88(16) . . ?
C8 C9 C10 129.24(17) . . ?
O12 C10 C9 109.56(17) . . ?
O11 C10 O12 123.31(18) . . ?
O11 C10 C9 127.12(19) . . ?
O17 C15 C8 113.73(16) . . ?
O16 C15 O17 124.26(17) . . ?
O16 C15 C8 122.01(17) . . ?
O38 C36 C29 109.87(16) . . ?
O37 C36 O38 124.96(18) . . ?
O37 C36 C29 125.16(18) . . ?
N25 C46 H46A 109.5 . . ?
N25 C46 H46B 109.5 . . ?
N25 C46 H46C 109.5 . . ?
H46A C46 H46B 109.5 . . ?
H46A C46 H46C 109.5 . . ?
H46B C46 H46C 109.5 . . ?
N2 C23 H23A 109.5 . . ?
N2 C23 H23B 109.5 . . ?
N2 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
O42 C43 H43A 109.5 . . ?
O42 C43 H43B 109.5 . . ?
O42 C43 H43C 109.5 . . ?
H43A C43 H43B 109.5 . . ?
H43A C43 H43C 109.5 . . ?
H43B C43 H43C 109.5 . . ?
O12 C13 H13A 110.2 . . ?
O12 C13 H13B 110.2 . . ?
O12 C13 C14 107.3(2) . . ?
H13A C13 H13B 108.5 . . ?
C14 C13 H13A 110.2 . . ?
C14 C13 H13B 110.2 . . ?
O33 C34 H34A 110.3 . . ?
O33 C34 H34B 110.3 . . ?
O33 C34 C35 107.01(17) . . ?
H34A C34 H34B 108.6 . . ?
C35 C34 H34A 110.3 . . ?
C35 C34 H34B 110.3 . . ?
O21 C22 H22A 109.5 . . ?
O21 C22 H22B 109.5 . . ?
O21 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
O38 C39 H39A 109.5 . . ?
O38 C39 H39B 109.5 . . ?
O38 C39 H39C 109.5 . . ?
H39A C39 H39B 109.5 . . ?
H39A C39 H39C 109.5 . . ?
H39B C39 H39C 109.5 . . ?
C34 C35 H35A 109.5 . . ?
C34 C35 H35B 109.5 . . ?
C34 C35 H35C 109.5 . . ?
H35A C35 H35B 109.5 . . ?
H35A C35 H35C 109.5 . . ?
H35B C35 H35C 109.5 . . ?
O17 C18 H18A 109.5 . . ?
O17 C18 H18B 109.5 . . ?
O17 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?

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
Br6 C5 C1 N2 179.36(13) . . . . ?
O42 C40 C28 C27 6.7(3) . . . . ?
O42 C40 C28 C29 -170.61(16) . . . . ?
O41 C40 C28 C27 -173.50(19) . . . . ?
O41 C40 C28 C29 9.2(3) . . . . ?
O20 C19 C7 C4 175.22(19) . . . . ?
O20 C19 C7 C8 0.7(3) . . . . ?
O21 C19 C7 C4 -4.1(3) . . . . ?
O21 C19 C7 C8 -178.68(16) . . . . ?
N26 N25 C24 C44 -0.6(2) . . . . ?
N26 C27 C28 C40 -175.73(18) . . . . ?
N26 C27 C28 C29 1.9(2) . . . . ?
N26 C27 C44 Br45 -179.50(13) . . . . ?
N26 C27 C44 C24 -0.9(2) . . . . ?
N26 C30 C29 C28 1.1(2) . . . . ?
N26 C30 C29 C36 179.54(16) . . . . ?
N26 C30 C31 O33 175.65(17) . . . . ?
N26 C30 C31 O32 -6.5(3) . . . . ?
N3 N2 C1 C5 2.9(2) . . . . ?
N3 C4 C5 Br6 178.10(14) . . . . ?
N3 C4 C5 C1 -2.0(2) . . . . ?
N3 C4 C7 C19 -172.94(18) . . . . ?
N3 C4 C7 C8 2.26(19) . . . . ?
N3 C9 C10 O12 173.36(16) . . . . ?
N3 C9 C10 O11 -7.3(3) . . . . ?
N2 N3 C4 C5 3.83(19) . . . . ?
N2 N3 C4 C7 -171.03(14) . . . . ?
N2 N3 C9 C8 165.84(18) . . . . ?
N2 N3 C9 C10 -22.5(3) . . . . ?
N25 N26 C27 C28 -175.84(15) . . . . ?
N25 N26 C27 C44 0.58(19) . . . . ?
N25 N26 C30 C29 172.56(19) . . . . ?
N25 N26 C30 C31 -17.5(3) . . . . ?
N25 C24 C44 Br45 179.63(13) . . . . ?
N25 C24 C44 C27 1.0(2) . . . . ?
C27 N26 N25 C24 0.0(2) . . . . ?
C27 N26 N25 C46 167.76(17) . . . . ?
C27 N26 C30 C29 0.1(2) . . . . ?
C27 N26 C30 C31 169.98(17) . . . . ?
C27 C28 C29 C30 -1.9(2) . . . . ?
C27 C28 C29 C36 179.72(17) . . . . ?
C4 N3 N2 C1 -4.19(19) . . . . ?
C4 N3 N2 C23 -168.17(18) . . . . ?
C4 N3 C9 C8 0.99(19) . . . . ?
C4 N3 C9 C10 172.67(17) . . . . ?
C4 C5 C1 N2 -0.6(2) . . . . ?
C40 C28 C29 C30 175.94(17) . . . . ?
C40 C28 C29 C36 -2.4(3) . . . . ?
C28 C27 C44 Br45 -5.9(4) . . . . ?
C28 C27 C44 C24 172.7(3) . . . . ?
C28 C29 C36 O38 -93.3(2) . . . . ?
C28 C29 C36 O37 86.2(3) . . . . ?
C30 N26 N25 C24 -172.5(2) . . . . ?
C30 N26 N25 C46 -4.8(3) . . . . ?
C30 N26 C27 C28 -1.3(2) . . . . ?
C30 N26 C27 C44 175.17(15) . . . . ?
C30 C29 C36 O38 88.5(2) . . . . ?
C30 C29 C36 O37 -91.9(3) . . . . ?
C29 C30 C31 O33 -17.0(3) . . . . ?
C29 C30 C31 O32 160.9(2) . . . . ?
C31 O33 C34 C35 -168.65(18) . . . . ?
C31 C30 C29 C28 -168.26(18) . . . . ?
C31 C30 C29 C36 10.1(3) . . . . ?
C5 C4 C7 C19 16.3(4) . . . . ?
C5 C4 C7 C8 -168.5(3) . . . . ?
C44 C27 C28 C40 10.7(4) . . . . ?
C44 C27 C28 C29 -171.7(3) . . . . ?
C8 C9 C10 O12 -17.0(3) . . . . ?
C8 C9 C10 O11 162.3(2) . . . . ?
C7 C4 C5 Br6 -11.1(4) . . . . ?
C7 C4 C5 C1 168.8(3) . . . . ?
C7 C8 C9 N3 0.5(2) . . . . ?
C7 C8 C9 C10 -170.72(18) . . . . ?
C7 C8 C15 O17 96.5(2) . . . . ?
C7 C8 C15 O16 -83.6(3) . . . . ?
C9 N3 N2 C1 -169.19(19) . . . . ?
C9 N3 N2 C23 26.8(3) . . . . ?
C9 N3 C4 C5 172.80(15) . . . . ?
C9 N3 C4 C7 -2.06(19) . . . . ?
C9 C8 C7 C4 -1.7(2) . . . . ?
C9 C8 C7 C19 173.93(16) . . . . ?
C9 C8 C15 O17 -94.3(2) . . . . ?
C9 C8 C15 O16 85.6(2) . . . . ?
C10 O12 C13 C14 173.3(2) . . . . ?
C15 C8 C7 C4 168.78(17) . . . . ?
C15 C8 C7 C19 -15.5(3) . . . . ?
C15 C8 C9 N3 -170.02(16) . . . . ?
C15 C8 C9 C10 18.8(3) . . . . ?
C46 N25 C24 C44 -168.14(18) . . . . ?
C23 N2 C1 C5 166.89(18) . . . . ?
C43 O42 C40 O41 -0.6(3) . . . . ?
C43 O42 C40 C28 179.22(16) . . . . ?
C13 O12 C10 O11 -4.0(3) . . . . ?
C13 O12 C10 C9 175.33(16) . . . . ?
C34 O33 C31 O32 -5.6(3) . . . . ?
C34 O33 C31 C30 172.26(17) . . . . ?
C22 O21 C19 O20 -5.5(3) . . . . ?
C22 O21 C19 C7 173.83(17) . . . . ?
C39 O38 C36 O37 3.2(3) . . . . ?
C39 O38 C36 C29 -177.26(17) . . . . ?
C18 O17 C15 O16 1.1(3) . . . . ?
C18 O17 C15 C8 -179.05(18) . . . . ?

_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 1.479
_oxdiff_exptl_absorpt_empirical_full_min 0.768
