# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_lkl11_auto
_database_code_depnum_ccdc_archive 'CCDC 2247659'
loop_
_audit_author_name
_audit_author_address
'LI kuiliang'
;University of  Science and Technology of China
China
;
_audit_update_record             
;
2023-03-10 deposited with the CCDC.	2023-05-10 downloaded from the CCDC.
;
_audit_creation_date             2022-09-30
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C27 H23 Br N2 O4'
_chemical_formula_sum            'C27 H23 Br N2 O4'
_chemical_formula_weight         519.38
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         c20h20o2n2c
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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   10.19020(11)
_cell_length_b                   11.29931(13)
_cell_length_c                   21.3624(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2459.72(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7465
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      72.9670
_cell_measurement_theta_min      5.6950
_shelx_estimated_absorpt_T_max   0.627
_shelx_estimated_absorpt_T_min   0.577
_exptl_absorpt_coefficient_mu    2.570
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.82541
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.110a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.403
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1064
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.2
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0232
_diffrn_reflns_av_unetI/netI     0.0270
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            9093
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.969
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.992
_diffrn_reflns_theta_min         4.139
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2169
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -119.00  -3.00   1.00    2.00    --  -41.76 -19.00  60.00  116
  2  ω     10.00  44.00   1.00    2.00    --   41.76 -77.00 -90.00   34
  3  ω     55.00  93.00   1.00    2.00    --   41.76-125.00 -60.00   38
  4  ω    131.00 175.00   1.00    4.00    --  106.05  77.00 -30.00   44
  5  ω     82.00 112.00   1.00    4.00    --  106.05-125.00  90.00   30
  6  ω    107.00 154.00   1.00    4.00    --  106.05  77.00 -60.00   47
  7  ω     82.00 108.00   1.00    4.00    --  106.05-125.00-180.00   26
  8  ω     35.00 131.00   1.00    4.00    --  106.05 -61.00 -60.00   96
  9  ω     78.00 178.00   1.00    4.00    --  106.05  30.00 -90.00  100
 10  ω     34.00 104.00   1.00    4.00    --  106.05 -94.00 -90.00   70
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0767851000
_diffrn_orient_matrix_UB_12      -0.1174167000
_diffrn_orient_matrix_UB_13      0.0001340000
_diffrn_orient_matrix_UB_21      0.1290210000
_diffrn_orient_matrix_UB_22      0.0686384000
_diffrn_orient_matrix_UB_23      0.0096930000
_diffrn_orient_matrix_UB_31      -0.0176629000
_diffrn_orient_matrix_UB_32      -0.0091083000
_diffrn_orient_matrix_UB_33      0.0714788000
_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              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.732
_reflns_Friedel_fraction_full    0.995
_reflns_Friedel_fraction_max     0.946
_reflns_number_gt                4696
_reflns_number_total             4766
_reflns_odcompleteness_completeness 99.92
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 1.171.41.110a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.110a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.110a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2013/4 (Sheldrick, 2015)'
_computing_structure_solution    ?
_refine_diff_density_max         0.206
_refine_diff_density_min         -0.541
_refine_diff_density_rms         0.075
_refine_ls_abs_structure_details 
;
 Flack x determined using 1962 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   -0.007(6)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     309
_refine_ls_number_reflns         4766
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0326
_refine_ls_R_factor_gt           0.0322
_refine_ls_restrained_S_all      1.074
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0401P)²+0.7713P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0816
_refine_ls_wR_factor_ref         0.0820
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1.a Ternary CH refined with riding coordinates:
 C7(H7)
1.b Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C19(H19A,H19B)
1.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C5(H5), C14(H14), C2(H2A), C3(H3), C21(H21), C15(H15), C18(H18),
 C22(H22), C16(H16), C25(H25), C17(H17), C23(H23), C24(H24)
1.d Idealised Me refined as rotating group:
 C27(H27A,H27B,H27C)
1.e Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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 0.86164(3) 0.44836(4) 0.32336(2) 0.05647(14) Uani 1 1 d . . . . .
O1 O 0.0761(2) 0.2102(2) 0.25013(9) 0.0381(5) Uani 1 1 d . . . . .
O2 O 0.1228(2) 0.5524(2) 0.13588(10) 0.0458(5) Uani 1 1 d . . . . .
H2 H 0.0571 0.5804 0.1524 0.069 Uiso 1 1 calc R U . . .
O3 O 0.3830(3) 0.3726(2) 0.14606(15) 0.0590(7) Uani 1 1 d . . . . .
O4 O 0.3821(3) 0.5691(2) 0.13674(15) 0.0619(7) Uani 1 1 d . . . . .
N1 N 0.0950(3) 0.1765(2) 0.31421(12) 0.0398(6) Uani 1 1 d . . . . .
N2 N 0.1259(3) 0.3687(2) 0.18587(11) 0.0361(5) Uani 1 1 d . . . . .
C9 C 0.1325(3) 0.3166(2) 0.24271(12) 0.0305(5) Uani 1 1 d . . . . .
C8 C 0.1873(3) 0.3565(3) 0.29709(13) 0.0298(5) Uani 1 1 d . . . . .
C12 C 0.1600(3) 0.2643(3) 0.34036(13) 0.0323(6) Uani 1 1 d . . . . .
C13 C 0.1951(3) 0.2546(3) 0.40735(14) 0.0386(7) Uani 1 1 d . . . . .
C7 C 0.2549(3) 0.4749(2) 0.29836(13) 0.0310(6) Uani 1 1 d . . . . .
H7 H 0.2281 0.5148 0.3370 0.037 Uiso 1 1 calc R U . . .
C6 C 0.6065(3) 0.3548(3) 0.30875(18) 0.0474(8) Uani 1 1 d . . . . .
H6 H 0.6488 0.2820 0.3114 0.057 Uiso 1 1 calc R U . . .
C26 C 0.3302(3) 0.4659(3) 0.15181(15) 0.0388(7) Uani 1 1 d . . . . .
C11 C 0.1978(3) 0.5462(3) 0.24340(13) 0.0342(6) Uani 1 1 d . . . . .
H11A H 0.1096 0.5705 0.2547 0.041 Uiso 1 1 calc R U . . .
H11B H 0.2498 0.6175 0.2386 0.041 Uiso 1 1 calc R U . . .
C19 C 0.0998(3) 0.2990(3) 0.12943(14) 0.0434(8) Uani 1 1 d . . . . .
H19A H 0.1414 0.2223 0.1341 0.052 Uiso 1 1 calc R U . . .
H19B H 0.1408 0.3382 0.0941 0.052 Uiso 1 1 calc R U . . .
C10 C 0.1913(3) 0.4838(3) 0.17958(14) 0.0333(6) Uani 1 1 d . . . . .
C1 C 0.6766(3) 0.4576(3) 0.31161(15) 0.0403(7) Uani 1 1 d . . . . .
C5 C 0.4710(3) 0.3605(3) 0.30186(18) 0.0435(7) Uani 1 1 d . . . . .
H5 H 0.4234 0.2905 0.2990 0.052 Uiso 1 1 calc R U . . .
C4 C 0.4050(3) 0.4672(3) 0.29910(13) 0.0321(6) Uani 1 1 d . . . . .
C14 C 0.1723(5) 0.1508(4) 0.43956(19) 0.0672(12) Uani 1 1 d . . . . .
H14 H 0.1332 0.0868 0.4195 0.081 Uiso 1 1 calc R U . . .
C20 C -0.0435(4) 0.2797(3) 0.11431(15) 0.0462(8) Uani 1 1 d . . . . .
C2 C 0.6157(3) 0.5660(3) 0.3070(2) 0.0547(9) Uani 1 1 d . . . . .
H2A H 0.6646 0.6355 0.3076 0.066 Uiso 1 1 calc R U . . .
C3 C 0.4798(3) 0.5698(3) 0.30153(19) 0.0500(9) Uani 1 1 d . . . . .
H3 H 0.4380 0.6428 0.2994 0.060 Uiso 1 1 calc R U . . .
C21 C -0.1462(4) 0.3295(4) 0.1472(2) 0.0573(9) Uani 1 1 d . . . . .
H21 H -0.1289 0.3782 0.1813 0.069 Uiso 1 1 calc R U . . .
C15 C 0.2084(7) 0.1427(6) 0.5022(2) 0.0873(17) Uani 1 1 d . . . . .
H15 H 0.1922 0.0729 0.5240 0.105 Uiso 1 1 calc R U . . .
C18 C 0.2611(6) 0.3432(4) 0.43751(18) 0.0682(13) Uani 1 1 d . . . . .
H18 H 0.2822 0.4118 0.4157 0.082 Uiso 1 1 calc R U . . .
C22 C -0.2741(5) 0.3078(5) 0.1298(3) 0.0828(16) Uani 1 1 d . . . . .
H22 H -0.3423 0.3420 0.1524 0.099 Uiso 1 1 calc R U . . .
C16 C 0.2672(6) 0.2351(5) 0.53242(19) 0.0796(15) Uani 1 1 d . . . . .
H16 H 0.2862 0.2302 0.5749 0.096 Uiso 1 1 calc R U . . .
C27 C 0.5095(5) 0.5671(5) 0.1074(3) 0.0906(18) Uani 1 1 d . . . . .
H27A H 0.5103 0.5084 0.0750 0.136 Uiso 1 1 calc R U . . .
H27B H 0.5750 0.5481 0.1381 0.136 Uiso 1 1 calc R U . . .
H27C H 0.5280 0.6433 0.0897 0.136 Uiso 1 1 calc R U . . .
C25 C -0.0725(6) 0.2040(6) 0.0646(2) 0.0858(17) Uani 1 1 d . . . . .
H25 H -0.0057 0.1657 0.0429 0.103 Uiso 1 1 calc R U . . .
C17 C 0.2971(7) 0.3330(5) 0.4998(2) 0.0828(16) Uani 1 1 d . . . . .
H17 H 0.3423 0.3944 0.5192 0.099 Uiso 1 1 calc R U . . .
C23 C -0.3025(7) 0.2368(8) 0.0801(4) 0.113(3) Uani 1 1 d . . . . .
H23 H -0.3891 0.2231 0.0685 0.135 Uiso 1 1 calc R U . . .
C24 C -0.2041(9) 0.1870(8) 0.0479(3) 0.122(3) Uani 1 1 d . . . . .
H24 H -0.2238 0.1397 0.0136 0.146 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 C1 1.905(3) . ?
O1 N1 1.434(3) . ?
O1 C9 1.342(3) . ?
O2 H2 0.8200 . ?
O2 C10 1.399(3) . ?
O3 C26 1.190(4) . ?
O4 C26 1.321(4) . ?
O4 C27 1.441(5) . ?
N1 C12 1.317(4) . ?
N2 C9 1.351(4) . ?
N2 C19 1.465(4) . ?
N2 C10 1.468(4) . ?
C9 C8 1.365(4) . ?
C8 C12 1.420(4) . ?
C8 C7 1.505(4) . ?
C12 C13 1.479(4) . ?
C13 C14 1.380(5) . ?
C13 C18 1.367(5) . ?
C7 H7 0.9800 . ?
C7 C11 1.538(4) . ?
C7 C4 1.532(4) . ?
C6 H6 0.9300 . ?
C6 C1 1.366(5) . ?
C6 C5 1.390(5) . ?
C26 C10 1.548(4) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 C10 1.536(4) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C19 C20 1.511(5) . ?
C1 C2 1.377(5) . ?
C5 H5 0.9300 . ?
C5 C4 1.382(4) . ?
C4 C3 1.388(4) . ?
C14 H14 0.9300 . ?
C14 C15 1.391(6) . ?
C20 C21 1.380(6) . ?
C20 C25 1.395(6) . ?
C2 H2A 0.9300 . ?
C2 C3 1.390(5) . ?
C3 H3 0.9300 . ?
C21 H21 0.9300 . ?
C21 C22 1.378(6) . ?
C15 H15 0.9300 . ?
C15 C16 1.366(8) . ?
C18 H18 0.9300 . ?
C18 C17 1.386(6) . ?
C22 H22 0.9300 . ?
C22 C23 1.363(10) . ?
C16 H16 0.9300 . ?
C16 C17 1.342(7) . ?
C27 H27A 0.9600 . ?
C27 H27B 0.9600 . ?
C27 H27C 0.9600 . ?
C25 H25 0.9300 . ?
C25 C24 1.401(9) . ?
C17 H17 0.9300 . ?
C23 H23 0.9300 . ?
C23 C24 1.339(12) . ?
C24 H24 0.9300 . ?

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
C9 O1 N1 107.1(2) . . ?
C10 O2 H2 109.5 . . ?
C26 O4 C27 116.9(3) . . ?
C12 N1 O1 105.8(2) . . ?
C9 N2 C19 121.0(3) . . ?
C9 N2 C10 116.5(2) . . ?
C19 N2 C10 118.9(2) . . ?
O1 C9 N2 118.4(2) . . ?
O1 C9 C8 111.7(2) . . ?
N2 C9 C8 129.9(3) . . ?
C9 C8 C12 103.4(2) . . ?
C9 C8 C7 119.7(2) . . ?
C12 C8 C7 136.9(3) . . ?
N1 C12 C8 112.0(2) . . ?
N1 C12 C13 118.5(3) . . ?
C8 C12 C13 129.5(3) . . ?
C14 C13 C12 120.3(3) . . ?
C18 C13 C12 121.4(3) . . ?
C18 C13 C14 118.1(3) . . ?
C8 C7 H7 107.2 . . ?
C8 C7 C11 106.2(2) . . ?
C8 C7 C4 114.1(2) . . ?
C11 C7 H7 107.2 . . ?
C4 C7 H7 107.2 . . ?
C4 C7 C11 114.5(2) . . ?
C1 C6 H6 120.5 . . ?
C1 C6 C5 119.0(3) . . ?
C5 C6 H6 120.5 . . ?
O3 C26 O4 125.1(3) . . ?
O3 C26 C10 124.7(3) . . ?
O4 C26 C10 110.2(3) . . ?
C7 C11 H11A 108.1 . . ?
C7 C11 H11B 108.1 . . ?
H11A C11 H11B 107.3 . . ?
C10 C11 C7 117.0(2) . . ?
C10 C11 H11A 108.1 . . ?
C10 C11 H11B 108.1 . . ?
N2 C19 H19A 108.4 . . ?
N2 C19 H19B 108.4 . . ?
N2 C19 C20 115.4(3) . . ?
H19A C19 H19B 107.5 . . ?
C20 C19 H19A 108.4 . . ?
C20 C19 H19B 108.4 . . ?
O2 C10 N2 109.0(2) . . ?
O2 C10 C26 105.8(2) . . ?
O2 C10 C11 111.1(2) . . ?
N2 C10 C26 109.5(2) . . ?
N2 C10 C11 110.2(2) . . ?
C11 C10 C26 111.1(2) . . ?
C6 C1 Br1 118.5(2) . . ?
C6 C1 C2 121.2(3) . . ?
C2 C1 Br1 120.3(2) . . ?
C6 C5 H5 119.0 . . ?
C4 C5 C6 121.9(3) . . ?
C4 C5 H5 119.0 . . ?
C5 C4 C7 122.4(3) . . ?
C5 C4 C3 117.3(3) . . ?
C3 C4 C7 120.1(3) . . ?
C13 C14 H14 120.3 . . ?
C13 C14 C15 119.4(5) . . ?
C15 C14 H14 120.3 . . ?
C21 C20 C19 124.4(3) . . ?
C21 C20 C25 118.5(4) . . ?
C25 C20 C19 117.1(4) . . ?
C1 C2 H2A 120.6 . . ?
C1 C2 C3 118.8(3) . . ?
C3 C2 H2A 120.6 . . ?
C4 C3 C2 121.7(3) . . ?
C4 C3 H3 119.2 . . ?
C2 C3 H3 119.2 . . ?
C20 C21 H21 119.8 . . ?
C22 C21 C20 120.5(5) . . ?
C22 C21 H21 119.8 . . ?
C14 C15 H15 119.3 . . ?
C16 C15 C14 121.3(5) . . ?
C16 C15 H15 119.3 . . ?
C13 C18 H18 119.3 . . ?
C13 C18 C17 121.5(4) . . ?
C17 C18 H18 119.3 . . ?
C21 C22 H22 119.5 . . ?
C23 C22 C21 121.0(6) . . ?
C23 C22 H22 119.5 . . ?
C15 C16 H16 120.5 . . ?
C17 C16 C15 119.0(4) . . ?
C17 C16 H16 120.5 . . ?
O4 C27 H27A 109.5 . . ?
O4 C27 H27B 109.5 . . ?
O4 C27 H27C 109.5 . . ?
H27A C27 H27B 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C20 C25 H25 120.7 . . ?
C20 C25 C24 118.6(6) . . ?
C24 C25 H25 120.7 . . ?
C18 C17 H17 119.8 . . ?
C16 C17 C18 120.4(5) . . ?
C16 C17 H17 119.8 . . ?
C22 C23 H23 120.4 . . ?
C24 C23 C22 119.3(5) . . ?
C24 C23 H23 120.4 . . ?
C25 C24 H24 119.0 . . ?
C23 C24 C25 122.0(6) . . ?
C23 C24 H24 119.0 . . ?

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
Br1 C1 C2 C3 -176.9(3) . . . . ?
O1 N1 C12 C8 -0.2(3) . . . . ?
O1 N1 C12 C13 -179.6(3) . . . . ?
O1 C9 C8 C12 0.0(3) . . . . ?
O1 C9 C8 C7 -179.7(3) . . . . ?
O3 C26 C10 O2 -128.4(4) . . . . ?
O3 C26 C10 N2 -11.1(4) . . . . ?
O3 C26 C10 C11 110.9(4) . . . . ?
O4 C26 C10 O2 52.9(4) . . . . ?
O4 C26 C10 N2 170.2(3) . . . . ?
O4 C26 C10 C11 -67.8(3) . . . . ?
N1 O1 C9 N2 -178.9(3) . . . . ?
N1 O1 C9 C8 -0.2(3) . . . . ?
N1 C12 C13 C14 6.8(5) . . . . ?
N1 C12 C13 C18 -179.1(4) . . . . ?
N2 C9 C8 C12 178.6(3) . . . . ?
N2 C9 C8 C7 -1.2(5) . . . . ?
N2 C19 C20 C21 4.7(5) . . . . ?
N2 C19 C20 C25 -173.8(4) . . . . ?
C9 O1 N1 C12 0.3(3) . . . . ?
C9 N2 C19 C20 86.8(4) . . . . ?
C9 N2 C10 O2 -148.3(3) . . . . ?
C9 N2 C10 C26 96.3(3) . . . . ?
C9 N2 C10 C11 -26.2(3) . . . . ?
C9 C8 C12 N1 0.2(3) . . . . ?
C9 C8 C12 C13 179.5(3) . . . . ?
C9 C8 C7 C11 22.8(3) . . . . ?
C9 C8 C7 C4 -104.3(3) . . . . ?
C8 C12 C13 C14 -172.5(4) . . . . ?
C8 C12 C13 C18 1.6(6) . . . . ?
C8 C7 C11 C10 -48.3(3) . . . . ?
C8 C7 C4 C5 -3.4(4) . . . . ?
C8 C7 C4 C3 -178.7(3) . . . . ?
C12 C8 C7 C11 -156.9(3) . . . . ?
C12 C8 C7 C4 76.0(4) . . . . ?
C12 C13 C14 C15 178.7(5) . . . . ?
C12 C13 C18 C17 -178.2(5) . . . . ?
C13 C14 C15 C16 -0.7(9) . . . . ?
C13 C18 C17 C16 -0.3(9) . . . . ?
C7 C8 C12 N1 179.8(3) . . . . ?
C7 C8 C12 C13 -0.8(6) . . . . ?
C7 C11 C10 O2 172.5(2) . . . . ?
C7 C11 C10 N2 51.7(3) . . . . ?
C7 C11 C10 C26 -69.9(3) . . . . ?
C7 C4 C3 C2 175.1(3) . . . . ?
C6 C1 C2 C3 2.2(6) . . . . ?
C6 C5 C4 C7 -173.5(3) . . . . ?
C6 C5 C4 C3 2.0(5) . . . . ?
C11 C7 C4 C5 -126.0(3) . . . . ?
C11 C7 C4 C3 58.7(4) . . . . ?
C19 N2 C9 O1 -20.5(4) . . . . ?
C19 N2 C9 C8 161.1(3) . . . . ?
C19 N2 C10 O2 52.9(3) . . . . ?
C19 N2 C10 C26 -62.5(3) . . . . ?
C19 N2 C10 C11 175.0(3) . . . . ?
C19 C20 C21 C22 179.5(4) . . . . ?
C19 C20 C25 C24 -178.0(6) . . . . ?
C10 N2 C9 O1 -178.8(2) . . . . ?
C10 N2 C9 C8 2.8(5) . . . . ?
C10 N2 C19 C20 -115.4(3) . . . . ?
C1 C6 C5 C4 -1.3(6) . . . . ?
C1 C2 C3 C4 -1.5(6) . . . . ?
C5 C6 C1 Br1 178.3(3) . . . . ?
C5 C6 C1 C2 -0.8(5) . . . . ?
C5 C4 C3 C2 -0.5(6) . . . . ?
C4 C7 C11 C10 78.5(3) . . . . ?
C14 C13 C18 C17 -4.1(8) . . . . ?
C14 C15 C16 C17 -3.7(10) . . . . ?
C20 C21 C22 C23 0.0(8) . . . . ?
C20 C25 C24 C23 -3.1(12) . . . . ?
C21 C20 C25 C24 3.4(8) . . . . ?
C21 C22 C23 C24 0.5(11) . . . . ?
C15 C16 C17 C18 4.2(10) . . . . ?
C18 C13 C14 C15 4.5(7) . . . . ?
C22 C23 C24 C25 1.1(13) . . . . ?
C27 O4 C26 O3 4.1(6) . . . . ?
C27 O4 C26 C10 -177.2(4) . . . . ?
C25 C20 C21 C22 -2.0(6) . . . . ?

_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 1.217
_oxdiff_exptl_absorpt_empirical_full_min 0.804
