# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2021

####################################################################### 
# 
# 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_222
_database_code_depnum_ccdc_archive 'CCDC 1968673'
loop_
_audit_author_name
_audit_author_address
'Guizhou Yue'
;Sichuan Agricultural University
China
;
_audit_update_record             
;
2019-11-28 deposited with the CCDC.	2021-05-26 downloaded from the CCDC.
;
_audit_creation_date             2019-11-25
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C26 H20 Br N3 O3'
_chemical_formula_sum            'C26 H20 Br N3 O3'
_chemical_formula_weight         502.36
_chemical_melting_point          ?
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           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   8.6861(14)
_cell_length_b                   21.538(3)
_cell_length_c                   13.065(2)
_cell_angle_alpha                90
_cell_angle_beta                 109.378(5)
_cell_angle_gamma                90
_cell_volume                     2305.8(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9902
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.165
_cell_measurement_theta_min      3.124
_shelx_estimated_absorpt_T_max   0.812
_shelx_estimated_absorpt_T_min   0.670
_exptl_absorpt_coefficient_mu    1.816
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5226
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0876 before and 0.0511 after correction.
The Ratio of minimum to maximum transmission is 0.7009.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.447
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1024
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0385
_diffrn_reflns_av_unetI/netI     0.0244
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            48525
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.613
_diffrn_reflns_theta_min         3.124
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4007
_reflns_number_total             5330
_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       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_refine_diff_density_max         1.624
_refine_diff_density_min         -1.607
_refine_diff_density_rms         0.074
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     298
_refine_ls_number_reflns         5330
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0786
_refine_ls_R_factor_gt           0.0547
_refine_ls_restrained_S_all      1.030
_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)+(0.0559P)²+3.5708P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1274
_refine_ls_wR_factor_ref         0.1412
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2.a Ternary CH refined with riding coordinates:
 C9(H9)
2.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B)
2.c Aromatic/amide H refined with riding coordinates:
 N3(H3), N1(H1), C17(H17), C24(H24), C11(H11), C14(H14), C19(H19), C16(H16),
 C6(H6), C2(H2), C25(H25), C15(H15), C18(H18), C12(H12), C13(H13), C3(H3A),
 C5(H5)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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 0.30823(5) 0.47353(2) 0.73328(3) 0.06413(16) Uani 1 1 d . . . . .
N3 N 1.1226(3) 0.47473(11) 1.4283(2) 0.0335(5) Uani 1 1 d . . . . .
H3 H 1.047589 0.457460 1.447969 0.040 Uiso 1 1 calc R . . . .
O2 O 1.2634(3) 0.38770(13) 1.18125(19) 0.0548(6) Uani 1 1 d . . . . .
N2 N 1.2157(3) 0.44803(11) 1.37379(19) 0.0320(5) Uani 1 1 d . . . . .
O1 O 0.6957(2) 0.34878(11) 1.23269(18) 0.0425(5) Uani 1 1 d . . . . .
C26 C 1.1735(4) 0.53293(14) 1.4442(2) 0.0374(7) Uani 1 1 d . . . . .
C1 C 0.4501(4) 0.44175(16) 0.8667(3) 0.0463(8) Uani 1 1 d . . . . .
C9 C 1.0329(3) 0.35712(13) 1.3150(2) 0.0292(6) Uani 1 1 d . . . . .
H9 H 0.983487 0.370258 1.368875 0.035 Uiso 1 1 calc R . . . .
C20 C 1.4531(3) 0.32191(14) 1.4334(3) 0.0390(7) Uani 1 1 d . . . . .
N1 N 1.4376(3) 0.33408(13) 1.3251(2) 0.0456(7) Uani 1 1 d . . . . .
H1 H 1.505580 0.321097 1.294777 0.055 Uiso 1 1 calc R . . . .
O3 O 1.1055(3) 0.57459(10) 1.4931(2) 0.0560(7) Uani 1 1 d . . . . .
C23 C 1.3037(4) 0.36854(15) 1.2733(3) 0.0388(7) Uani 1 1 d . . . . .
C21 C 1.3211(3) 0.34734(13) 1.4562(2) 0.0328(6) Uani 1 1 d . . . . .
C17 C 1.4338(5) 0.31130(17) 1.6380(3) 0.0546(9) Uani 1 1 d . . . . .
H17 H 1.428225 0.307431 1.707593 0.066 Uiso 1 1 calc R . . . .
C10 C 1.0198(3) 0.28675(13) 1.3088(2) 0.0328(6) Uani 1 1 d . . . . .
C24 C 1.3234(4) 0.48934(15) 1.3608(3) 0.0416(7) Uani 1 1 d . . . . .
H24 H 1.401428 0.481504 1.327955 0.050 Uiso 1 1 calc R . . . .
C8 C 0.9356(3) 0.38874(15) 1.2085(2) 0.0373(6) Uani 1 1 d . . . . .
H8A H 0.953380 0.433198 1.216382 0.045 Uiso 1 1 calc R . . . .
H8B H 0.976619 0.374652 1.151891 0.045 Uiso 1 1 calc R . . . .
C11 C 1.0387(4) 0.25253(17) 1.2243(3) 0.0481(8) Uani 1 1 d . . . . .
H11 H 1.069522 0.272377 1.170876 0.058 Uiso 1 1 calc R . . . .
C4 C 0.6521(3) 0.39858(14) 1.0647(2) 0.0366(6) Uani 1 1 d . . . . .
C14 C 0.9514(6) 0.1915(2) 1.3808(4) 0.0746(13) Uani 1 1 d . . . . .
H14 H 0.922226 0.171111 1.434378 0.090 Uiso 1 1 calc R . . . .
C19 C 1.5756(4) 0.29105(16) 1.5117(4) 0.0559(10) Uani 1 1 d . . . . .
H19 H 1.663372 0.273833 1.495930 0.067 Uiso 1 1 calc R . . . .
C16 C 1.3104(4) 0.34214(15) 1.5583(3) 0.0424(7) Uani 1 1 d . . . . .
H16 H 1.222165 0.358958 1.573987 0.051 Uiso 1 1 calc R . . . .
C7 C 0.7552(3) 0.37619(13) 1.1737(2) 0.0323(6) Uani 1 1 d . . . . .
C22 C 1.2122(3) 0.38045(13) 1.3565(2) 0.0298(6) Uani 1 1 d . . . . .
C6 C 0.3927(4) 0.39840(18) 0.9221(3) 0.0558(9) Uani 1 1 d . . . . .
H6 H 0.286701 0.383369 0.892779 0.067 Uiso 1 1 calc R . . . .
C2 C 0.6062(5) 0.46411(19) 0.9071(3) 0.0579(10) Uani 1 1 d . . . . .
H2 H 0.643379 0.493791 0.869190 0.069 Uiso 1 1 calc R . . . .
C25 C 1.2995(4) 0.54453(16) 1.4036(3) 0.0475(8) Uani 1 1 d . . . . .
H25 H 1.354961 0.581662 1.405371 0.057 Uiso 1 1 calc R . . . .
C15 C 0.9767(5) 0.25534(17) 1.3872(3) 0.0533(9) Uani 1 1 d . . . . .
H15 H 0.964476 0.277221 1.445399 0.064 Uiso 1 1 calc R . . . .
C18 C 1.5641(5) 0.28648(16) 1.6144(3) 0.0600(10) Uani 1 1 d . . . . .
H18 H 1.646019 0.266212 1.668670 0.072 Uiso 1 1 calc R . . . .
C12 C 1.0121(5) 0.1888(2) 1.2181(4) 0.0662(12) Uani 1 1 d . . . . .
H12 H 1.023852 0.166566 1.160120 0.079 Uiso 1 1 calc R . . . .
C13 C 0.9691(5) 0.15853(18) 1.2959(4) 0.0687(12) Uani 1 1 d . . . . .
H13 H 0.951938 0.115848 1.291374 0.082 Uiso 1 1 calc R . . . .
C3 C 0.7076(4) 0.44156(19) 1.0058(3) 0.0540(9) Uani 1 1 d . . . . .
H3A H 0.814895 0.455472 1.033082 0.065 Uiso 1 1 calc R . . . .
C5 C 0.4929(4) 0.37728(17) 1.0215(3) 0.0487(8) Uani 1 1 d . . . . .
H5 H 0.453507 0.348532 1.059775 0.058 Uiso 1 1 calc R . . . .


_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 1.898(3) . ?
N3 H3 0.8600 . ?
N3 N2 1.369(3) . ?
N3 C26 1.323(4) . ?
O2 C23 1.208(4) . ?
N2 C24 1.342(4) . ?
N2 C22 1.472(4) . ?
O1 C7 1.214(4) . ?
C26 O3 1.346(4) . ?
C26 C25 1.388(5) . ?
C1 C6 1.373(5) . ?
C1 C2 1.369(5) . ?
C9 H9 0.9800 . ?
C9 C10 1.520(4) . ?
C9 C8 1.528(4) . ?
C9 C22 1.552(4) . ?
C20 N1 1.401(4) . ?
C20 C21 1.389(4) . ?
C20 C19 1.378(5) . ?
N1 H1 0.8600 . ?
N1 C23 1.356(4) . ?
C23 C22 1.566(4) . ?
C21 C16 1.373(4) . ?
C21 C22 1.510(4) . ?
C17 H17 0.9300 . ?
C17 C16 1.390(5) . ?
C17 C18 1.376(6) . ?
C10 C11 1.382(4) . ?
C10 C15 1.379(4) . ?
C24 H24 0.9300 . ?
C24 C25 1.359(5) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 C7 1.504(4) . ?
C11 H11 0.9300 . ?
C11 C12 1.390(6) . ?
C4 C7 1.489(4) . ?
C4 C3 1.389(5) . ?
C4 C5 1.387(4) . ?
C14 H14 0.9300 . ?
C14 C15 1.391(5) . ?
C14 C13 1.368(7) . ?
C19 H19 0.9300 . ?
C19 C18 1.382(6) . ?
C16 H16 0.9300 . ?
C6 H6 0.9300 . ?
C6 C5 1.378(5) . ?
C2 H2 0.9300 . ?
C2 C3 1.386(5) . ?
C25 H25 0.9300 . ?
C15 H15 0.9300 . ?
C18 H18 0.9300 . ?
C12 H12 0.9300 . ?
C12 C13 1.359(7) . ?
C13 H13 0.9300 . ?
C3 H3A 0.9300 . ?
C5 H5 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
N2 N3 H3 127.6 . . ?
C26 N3 H3 127.6 . . ?
C26 N3 N2 104.8(2) . . ?
N3 N2 C22 120.6(2) . . ?
C24 N2 N3 110.1(2) . . ?
C24 N2 C22 128.0(2) . . ?
N3 C26 O3 122.0(3) . . ?
N3 C26 C25 112.1(3) . . ?
O3 C26 C25 125.9(3) . . ?
C6 C1 Br1 119.4(3) . . ?
C2 C1 Br1 119.0(3) . . ?
C2 C1 C6 121.5(3) . . ?
C10 C9 H9 106.5 . . ?
C10 C9 C8 112.7(2) . . ?
C10 C9 C22 113.0(2) . . ?
C8 C9 H9 106.5 . . ?
C8 C9 C22 111.2(2) . . ?
C22 C9 H9 106.5 . . ?
C21 C20 N1 109.4(3) . . ?
C19 C20 N1 129.2(3) . . ?
C19 C20 C21 121.4(3) . . ?
C20 N1 H1 123.6 . . ?
C23 N1 C20 112.7(2) . . ?
C23 N1 H1 123.6 . . ?
O2 C23 N1 126.9(3) . . ?
O2 C23 C22 126.1(3) . . ?
N1 C23 C22 107.0(3) . . ?
C20 C21 C22 109.1(3) . . ?
C16 C21 C20 120.2(3) . . ?
C16 C21 C22 130.6(3) . . ?
C16 C17 H17 119.8 . . ?
C18 C17 H17 119.8 . . ?
C18 C17 C16 120.3(4) . . ?
C11 C10 C9 123.2(3) . . ?
C15 C10 C9 118.9(3) . . ?
C15 C10 C11 117.8(3) . . ?
N2 C24 H24 125.7 . . ?
N2 C24 C25 108.6(3) . . ?
C25 C24 H24 125.7 . . ?
C9 C8 H8A 108.8 . . ?
C9 C8 H8B 108.8 . . ?
H8A C8 H8B 107.7 . . ?
C7 C8 C9 113.7(2) . . ?
C7 C8 H8A 108.8 . . ?
C7 C8 H8B 108.8 . . ?
C10 C11 H11 119.6 . . ?
C10 C11 C12 120.8(4) . . ?
C12 C11 H11 119.6 . . ?
C3 C4 C7 122.5(3) . . ?
C5 C4 C7 119.0(3) . . ?
C5 C4 C3 118.5(3) . . ?
C15 C14 H14 119.9 . . ?
C13 C14 H14 119.9 . . ?
C13 C14 C15 120.3(4) . . ?
C20 C19 H19 121.0 . . ?
C20 C19 C18 117.9(3) . . ?
C18 C19 H19 121.0 . . ?
C21 C16 C17 118.9(3) . . ?
C21 C16 H16 120.6 . . ?
C17 C16 H16 120.6 . . ?
O1 C7 C8 121.1(3) . . ?
O1 C7 C4 121.1(3) . . ?
C4 C7 C8 117.8(2) . . ?
N2 C22 C9 109.9(2) . . ?
N2 C22 C23 106.2(2) . . ?
N2 C22 C21 111.1(2) . . ?
C9 C22 C23 112.7(2) . . ?
C21 C22 C9 114.7(2) . . ?
C21 C22 C23 101.8(2) . . ?
C1 C6 H6 120.2 . . ?
C1 C6 C5 119.6(3) . . ?
C5 C6 H6 120.2 . . ?
C1 C2 H2 120.7 . . ?
C1 C2 C3 118.5(3) . . ?
C3 C2 H2 120.7 . . ?
C26 C25 H25 127.8 . . ?
C24 C25 C26 104.3(3) . . ?
C24 C25 H25 127.8 . . ?
C10 C15 C14 121.1(4) . . ?
C10 C15 H15 119.5 . . ?
C14 C15 H15 119.5 . . ?
C17 C18 C19 121.3(3) . . ?
C17 C18 H18 119.3 . . ?
C19 C18 H18 119.3 . . ?
C11 C12 H12 119.6 . . ?
C13 C12 C11 120.8(4) . . ?
C13 C12 H12 119.6 . . ?
C14 C13 H13 120.3 . . ?
C12 C13 C14 119.3(4) . . ?
C12 C13 H13 120.3 . . ?
C4 C3 H3A 119.4 . . ?
C2 C3 C4 121.3(3) . . ?
C2 C3 H3A 119.4 . . ?
C4 C5 H5 119.7 . . ?
C6 C5 C4 120.5(3) . . ?
C6 C5 H5 119.7 . . ?

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 C6 C5 -177.0(3) . . . . ?
Br1 C1 C2 C3 178.6(3) . . . . ?
N3 N2 C24 C25 -1.9(4) . . . . ?
N3 N2 C22 C9 46.9(3) . . . . ?
N3 N2 C22 C23 169.1(2) . . . . ?
N3 N2 C22 C21 -81.1(3) . . . . ?
N3 C26 C25 C24 0.2(4) . . . . ?
O2 C23 C22 N2 -61.9(4) . . . . ?
O2 C23 C22 C9 58.5(4) . . . . ?
O2 C23 C22 C21 -178.2(3) . . . . ?
N2 N3 C26 O3 177.8(3) . . . . ?
N2 N3 C26 C25 -1.3(3) . . . . ?
N2 C24 C25 C26 1.0(4) . . . . ?
C26 N3 N2 C24 2.0(3) . . . . ?
C26 N3 N2 C22 170.4(2) . . . . ?
C1 C6 C5 C4 -1.3(6) . . . . ?
C1 C2 C3 C4 -1.9(6) . . . . ?
C9 C10 C11 C12 -174.7(3) . . . . ?
C9 C10 C15 C14 175.2(4) . . . . ?
C9 C8 C7 O1 7.2(4) . . . . ?
C9 C8 C7 C4 -172.9(2) . . . . ?
C20 N1 C23 O2 177.1(3) . . . . ?
C20 N1 C23 C22 -1.5(3) . . . . ?
C20 C21 C16 C17 0.2(5) . . . . ?
C20 C21 C22 N2 -111.9(3) . . . . ?
C20 C21 C22 C9 122.7(3) . . . . ?
C20 C21 C22 C23 0.8(3) . . . . ?
C20 C19 C18 C17 0.7(5) . . . . ?
N1 C20 C21 C16 -179.1(3) . . . . ?
N1 C20 C21 C22 -1.7(3) . . . . ?
N1 C20 C19 C18 178.5(3) . . . . ?
N1 C23 C22 N2 116.7(3) . . . . ?
N1 C23 C22 C9 -122.9(3) . . . . ?
N1 C23 C22 C21 0.4(3) . . . . ?
O3 C26 C25 C24 -178.8(3) . . . . ?
C21 C20 N1 C23 2.1(4) . . . . ?
C21 C20 C19 C18 -0.5(5) . . . . ?
C10 C9 C8 C7 61.5(3) . . . . ?
C10 C9 C22 N2 -172.8(2) . . . . ?
C10 C9 C22 C23 69.0(3) . . . . ?
C10 C9 C22 C21 -46.8(3) . . . . ?
C10 C11 C12 C13 -0.9(6) . . . . ?
C24 N2 C22 C9 -147.0(3) . . . . ?
C24 N2 C22 C23 -24.8(4) . . . . ?
C24 N2 C22 C21 85.0(3) . . . . ?
C8 C9 C10 C11 47.1(4) . . . . ?
C8 C9 C10 C15 -128.6(3) . . . . ?
C8 C9 C22 N2 59.3(3) . . . . ?
C8 C9 C22 C23 -58.9(3) . . . . ?
C8 C9 C22 C21 -174.7(2) . . . . ?
C11 C10 C15 C14 -0.7(5) . . . . ?
C11 C12 C13 C14 0.3(6) . . . . ?
C19 C20 N1 C23 -177.0(3) . . . . ?
C19 C20 C21 C16 0.0(5) . . . . ?
C19 C20 C21 C22 177.4(3) . . . . ?
C16 C21 C22 N2 65.1(4) . . . . ?
C16 C21 C22 C9 -60.3(4) . . . . ?
C16 C21 C22 C23 177.8(3) . . . . ?
C16 C17 C18 C19 -0.4(6) . . . . ?
C7 C4 C3 C2 -176.5(3) . . . . ?
C7 C4 C5 C6 178.2(3) . . . . ?
C22 N2 C24 C25 -169.2(3) . . . . ?
C22 C9 C10 C11 -80.0(3) . . . . ?
C22 C9 C10 C15 104.2(3) . . . . ?
C22 C9 C8 C7 -170.4(2) . . . . ?
C22 C21 C16 C17 -176.5(3) . . . . ?
C6 C1 C2 C3 0.7(6) . . . . ?
C2 C1 C6 C5 0.9(6) . . . . ?
C15 C10 C11 C12 1.1(5) . . . . ?
C15 C14 C13 C12 0.1(7) . . . . ?
C18 C17 C16 C21 0.0(5) . . . . ?
C13 C14 C15 C10 0.1(7) . . . . ?
C3 C4 C7 O1 165.1(3) . . . . ?
C3 C4 C7 C8 -14.8(4) . . . . ?
C3 C4 C5 C6 0.1(5) . . . . ?
C5 C4 C7 O1 -13.0(4) . . . . ?
C5 C4 C7 C8 167.2(3) . . . . ?
C5 C4 C3 C2 1.5(6) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_2
_database_code_depnum_ccdc_archive 'CCDC 1959582'
loop_
_audit_author_name
_audit_author_address
'Guizhou Yue'
;Sichuan Agricultural University
China
;
_audit_update_record             
;
2019-10-16 deposited with the CCDC.	2021-05-26 downloaded from the CCDC.
;
_audit_creation_date             2019-10-12
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C27 H21 Br N2 O3'
_chemical_formula_sum            'C27 H21 Br N2 O3'
_chemical_formula_weight         501.37
_chemical_absolute_configuration ?
_chemical_melting_point          ?
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      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x+1/2, y+1/2, z+1/2'
'x+1/2, -y+1/2, z'

_cell_length_a                   8.1785(14)
_cell_length_b                   25.516(4)
_cell_length_c                   12.111(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2527.3(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9874
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      25.26
_cell_measurement_theta_min      2.93
_shelx_estimated_absorpt_T_max   0.814
_shelx_estimated_absorpt_T_min   0.682
_exptl_absorpt_coefficient_mu    1.656
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.4099
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1507 before and 0.0791 after correction.
The Ratio of minimum to maximum transmission is 0.5498.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.318
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1024
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.13
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0593
_diffrn_reflns_av_unetI/netI     0.0553
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       33
_diffrn_reflns_limit_k_min       -32
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            31059
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.413
_diffrn_reflns_theta_min         2.927
_diffrn_ambient_temperature      273.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.886
_reflns_Friedel_fraction_full    0.983
_reflns_Friedel_fraction_max     0.972
_reflns_number_gt                3876
_reflns_number_total             5674
_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       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.727
_refine_diff_density_min         -0.799
_refine_diff_density_rms         0.095
_refine_ls_abs_structure_details 
;
 Flack x determined using 1367 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.052(6)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     298
_refine_ls_number_reflns         5674
_refine_ls_number_restraints     13
_refine_ls_R_factor_all          0.1140
_refine_ls_R_factor_gt           0.0776
_refine_ls_restrained_S_all      1.092
_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)+(0.1618P)²+0.7219P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2335
_refine_ls_wR_factor_ref         0.2613
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C18) \\sim Ueq, Uanis(C17) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
3.a Ternary CH refined with riding coordinates:
 C11(H11), C13(H13), C7(H7), C8(H8)
3.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B)
3.c Aromatic/amide H refined with riding coordinates:
 N1(H1), N2(H2), C22(H22), C24(H24), C20(H20), C25(H25), C23(H23), C5(H5),
 C2(H2A), C16(H16), C4(H4), C19(H19), C3(H3), C18(H18), C17(H17)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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 0.4939(2) 0.70163(5) 0.48523(16) 0.1107(7) Uani 1 1 d . . . . .
O3 O 0.0967(7) 0.5063(2) 0.1894(4) 0.0473(12) Uani 1 1 d . . . . .
C11 C 0.0380(7) 0.5534(3) 0.4074(6) 0.0285(12) Uani 1 1 d . . . . .
H11 H -0.064830 0.540549 0.376001 0.034 Uiso 1 1 calc R . . . .
N1 N 0.0222(9) 0.5651(3) 0.5239(6) 0.0481(17) Uani 1 1 d . . . . .
H1 H 0.036416 0.542501 0.575629 0.058 Uiso 1 1 calc R . . . .
C27 C 0.1249(9) 0.4865(3) 0.2782(6) 0.0388(15) Uani 1 1 d . . . . .
O1 O -0.0581(10) 0.6339(3) 0.6334(6) 0.072(2) Uani 1 1 d . . . . .
C12 C 0.1757(9) 0.5177(3) 0.3832(5) 0.0364(14) Uani 1 1 d . . . . .
N2 N 0.1202(9) 0.4348(3) 0.3058(6) 0.0486(16) Uani 1 1 d . . . . .
H2 H 0.092083 0.410170 0.261210 0.058 Uiso 1 1 calc R . . . .
C13 C 0.3276(9) 0.5533(3) 0.3509(5) 0.0379(15) Uani 1 1 d . . . . .
H13 H 0.345446 0.549721 0.271232 0.045 Uiso 1 1 calc R . . . .
O2 O 0.5412(9) 0.5634(3) 0.4826(8) 0.082(2) Uani 1 1 d . . . . .
C7 C 0.2708(10) 0.6098(3) 0.3730(6) 0.0445(17) Uani 1 1 d . . . . .
H7 H 0.297397 0.618725 0.449633 0.053 Uiso 1 1 calc R . . . .
C26 C 0.1668(9) 0.4267(3) 0.4155(7) 0.0439(17) Uani 1 1 d . . . . .
C14 C 0.4857(9) 0.5372(4) 0.4093(8) 0.0479(19) Uani 1 1 d . . . . .
C8 C 0.0830(10) 0.6064(3) 0.3620(6) 0.0443(17) Uani 1 1 d . . . . .
H8 H 0.048496 0.610094 0.284884 0.053 Uiso 1 1 calc R . . . .
C6 C 0.3463(10) 0.6511(3) 0.2976(7) 0.0473(17) Uani 1 1 d . . . . .
C22 C 0.2482(9) 0.4750(3) 0.5768(6) 0.0478(18) Uani 1 1 d . . . . .
H22 H 0.271542 0.506287 0.612886 0.057 Uiso 1 1 calc R . . . .
C21 C 0.2001(8) 0.4745(3) 0.4667(5) 0.0349(14) Uani 1 1 d . . . . .
C15 C 0.5644(9) 0.4871(3) 0.3762(8) 0.050(2) Uani 1 1 d . . . . .
C1 C 0.4427(15) 0.6914(4) 0.3330(8) 0.064(2) Uani 1 1 d . . . . .
C10 C -0.0179(11) 0.6161(4) 0.5416(8) 0.056(2) Uani 1 1 d . . . . .
C24 C 0.2243(13) 0.3819(4) 0.5833(10) 0.070(3) Uani 1 1 d . . . . .
H24 H 0.228420 0.351071 0.624291 0.084 Uiso 1 1 calc R . . . .
C20 C 0.5257(11) 0.4604(4) 0.2809(8) 0.057(2) Uani 1 1 d . . . . .
H20 H 0.448821 0.474647 0.233005 0.068 Uiso 1 1 calc R . . . .
C25 C 0.1799(12) 0.3794(3) 0.4717(9) 0.066(2) Uani 1 1 d . . . . .
H25 H 0.160111 0.347591 0.436819 0.079 Uiso 1 1 calc R . . . .
C23 C 0.2601(12) 0.4265(4) 0.6316(8) 0.065(3) Uani 1 1 d . . . . .
H23 H 0.294698 0.426038 0.704756 0.078 Uiso 1 1 calc R . . . .
C5 C 0.3204(12) 0.6488(4) 0.1856(7) 0.060(2) Uani 1 1 d . . . . .
H5 H 0.259169 0.621074 0.157917 0.072 Uiso 1 1 calc R . . . .
C2 C 0.5117(13) 0.7290(4) 0.2600(11) 0.074(3) Uani 1 1 d . . . . .
H2A H 0.579612 0.755439 0.286410 0.089 Uiso 1 1 calc R . . . .
C16 C 0.6807(11) 0.4650(5) 0.4463(9) 0.069(3) Uani 1 1 d . . . . .
H16 H 0.708514 0.481797 0.511793 0.083 Uiso 1 1 calc R . . . .
C4 C 0.3789(15) 0.6847(4) 0.1132(9) 0.076(3) Uani 1 1 d . . . . .
H4 H 0.353548 0.681846 0.038600 0.091 Uiso 1 1 calc R . . . .
C19 C 0.5978(16) 0.4127(4) 0.2542(10) 0.081(3) Uani 1 1 d . . . . .
H19 H 0.568150 0.394996 0.190122 0.097 Uiso 1 1 calc R . . . .
C3 C 0.4757(15) 0.7254(5) 0.1494(11) 0.084(4) Uani 1 1 d . . . . .
H3 H 0.516173 0.749997 0.099785 0.100 Uiso 1 1 calc R . . . .
C18 C 0.7139(18) 0.3922(5) 0.3242(13) 0.099(4) Uani 1 1 d . U . . .
H18 H 0.764729 0.360613 0.307160 0.119 Uiso 1 1 calc R . . . .
C9 C -0.0050(12) 0.6446(4) 0.4355(9) 0.063(3) Uani 1 1 d . . . . .
H9A H 0.057165 0.676749 0.444068 0.076 Uiso 1 1 calc R . . . .
H9B H -0.112298 0.653007 0.406342 0.076 Uiso 1 1 calc R . . . .
C17 C 0.7543(14) 0.4182(6) 0.4185(13) 0.091(4) Uani 1 1 d . U . . .
H17 H 0.833323 0.404176 0.465084 0.109 Uiso 1 1 calc R . . . .


_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 1.908(10) . ?
O3 C27 1.210(9) . ?
C11 H11 0.9800 . ?
C11 N1 1.448(10) . ?
C11 C12 1.478(10) . ?
C11 C8 1.505(9) . ?
N1 H1 0.8600 . ?
N1 C10 1.358(12) . ?
C27 C12 1.558(10) . ?
C27 N2 1.360(10) . ?
O1 C10 1.245(12) . ?
C12 C13 1.588(10) . ?
C12 C21 1.510(10) . ?
N2 H2 0.8600 . ?
N2 C26 1.398(10) . ?
C13 H13 0.9800 . ?
C13 C7 1.537(10) . ?
C13 C14 1.530(11) . ?
O2 C14 1.200(13) . ?
C7 H7 0.9800 . ?
C7 C8 1.544(12) . ?
C7 C6 1.526(10) . ?
C26 C21 1.394(10) . ?
C26 C25 1.390(11) . ?
C14 C15 1.487(13) . ?
C8 H8 0.9800 . ?
C8 C9 1.504(13) . ?
C6 C1 1.365(13) . ?
C6 C5 1.374(13) . ?
C22 H22 0.9300 . ?
C22 C21 1.390(10) . ?
C22 C23 1.408(12) . ?
C15 C20 1.377(14) . ?
C15 C16 1.394(13) . ?
C1 C2 1.422(15) . ?
C10 C9 1.480(12) . ?
C24 H24 0.9300 . ?
C24 C25 1.401(17) . ?
C24 C23 1.313(15) . ?
C20 H20 0.9300 . ?
C20 C19 1.390(15) . ?
C25 H25 0.9300 . ?
C23 H23 0.9300 . ?
C5 H5 0.9300 . ?
C5 C4 1.355(13) . ?
C2 H2A 0.9300 . ?
C2 C3 1.375(19) . ?
C16 H16 0.9300 . ?
C16 C17 1.378(18) . ?
C4 H4 0.9300 . ?
C4 C3 1.377(18) . ?
C19 H19 0.9300 . ?
C19 C18 1.38(2) . ?
C3 H3 0.9300 . ?
C18 H18 0.9300 . ?
C18 C17 1.36(2) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C17 H17 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
N1 C11 H11 111.7 . . ?
N1 C11 C12 112.9(6) . . ?
N1 C11 C8 101.1(6) . . ?
C12 C11 H11 111.7 . . ?
C12 C11 C8 107.2(6) . . ?
C8 C11 H11 111.7 . . ?
C11 N1 H1 124.1 . . ?
C10 N1 C11 111.9(7) . . ?
C10 N1 H1 124.1 . . ?
O3 C27 C12 124.1(6) . . ?
O3 C27 N2 128.2(7) . . ?
N2 C27 C12 107.6(6) . . ?
C11 C12 C27 105.9(6) . . ?
C11 C12 C13 107.0(5) . . ?
C11 C12 C21 114.8(6) . . ?
C27 C12 C13 107.5(5) . . ?
C21 C12 C27 102.0(6) . . ?
C21 C12 C13 118.6(6) . . ?
C27 N2 H2 124.2 . . ?
C27 N2 C26 111.7(6) . . ?
C26 N2 H2 124.2 . . ?
C12 C13 H13 107.7 . . ?
C7 C13 C12 104.9(6) . . ?
C7 C13 H13 107.7 . . ?
C14 C13 C12 113.2(6) . . ?
C14 C13 H13 107.7 . . ?
C14 C13 C7 115.3(6) . . ?
C13 C7 H7 108.4 . . ?
C13 C7 C8 103.5(6) . . ?
C8 C7 H7 108.4 . . ?
C6 C7 C13 114.9(6) . . ?
C6 C7 H7 108.4 . . ?
C6 C7 C8 112.9(7) . . ?
C21 C26 N2 110.3(6) . . ?
C25 C26 N2 128.0(8) . . ?
C25 C26 C21 121.7(8) . . ?
O2 C14 C13 120.8(8) . . ?
O2 C14 C15 121.0(8) . . ?
C15 C14 C13 118.1(8) . . ?
C11 C8 C7 105.2(6) . . ?
C11 C8 H8 111.3 . . ?
C7 C8 H8 111.3 . . ?
C9 C8 C11 104.4(6) . . ?
C9 C8 C7 112.9(8) . . ?
C9 C8 H8 111.3 . . ?
C1 C6 C7 124.5(8) . . ?
C1 C6 C5 115.6(8) . . ?
C5 C6 C7 119.9(7) . . ?
C21 C22 H22 121.2 . . ?
C21 C22 C23 117.6(8) . . ?
C23 C22 H22 121.2 . . ?
C26 C21 C12 108.4(6) . . ?
C22 C21 C12 132.3(7) . . ?
C22 C21 C26 119.4(7) . . ?
C20 C15 C14 123.6(8) . . ?
C20 C15 C16 117.8(9) . . ?
C16 C15 C14 118.6(9) . . ?
C6 C1 Br1 122.2(7) . . ?
C6 C1 C2 122.8(10) . . ?
C2 C1 Br1 115.0(8) . . ?
N1 C10 C9 108.5(8) . . ?
O1 C10 N1 123.6(8) . . ?
O1 C10 C9 127.9(8) . . ?
C25 C24 H24 119.1 . . ?
C23 C24 H24 119.1 . . ?
C23 C24 C25 121.7(9) . . ?
C15 C20 H20 119.0 . . ?
C15 C20 C19 122.1(10) . . ?
C19 C20 H20 119.0 . . ?
C26 C25 C24 117.0(9) . . ?
C26 C25 H25 121.5 . . ?
C24 C25 H25 121.5 . . ?
C22 C23 H23 118.8 . . ?
C24 C23 C22 122.4(9) . . ?
C24 C23 H23 118.8 . . ?
C6 C5 H5 118.1 . . ?
C4 C5 C6 123.7(9) . . ?
C4 C5 H5 118.1 . . ?
C1 C2 H2A 120.8 . . ?
C3 C2 C1 118.4(10) . . ?
C3 C2 H2A 120.8 . . ?
C15 C16 H16 120.0 . . ?
C17 C16 C15 120.0(12) . . ?
C17 C16 H16 120.0 . . ?
C5 C4 H4 119.8 . . ?
C5 C4 C3 120.4(11) . . ?
C3 C4 H4 119.8 . . ?
C20 C19 H19 120.6 . . ?
C18 C19 C20 118.8(13) . . ?
C18 C19 H19 120.6 . . ?
C2 C3 C4 119.0(10) . . ?
C2 C3 H3 120.5 . . ?
C4 C3 H3 120.5 . . ?
C19 C18 H18 120.0 . . ?
C17 C18 C19 119.9(12) . . ?
C17 C18 H18 120.0 . . ?
C8 C9 H9A 111.1 . . ?
C8 C9 H9B 111.1 . . ?
C10 C9 C8 103.2(7) . . ?
C10 C9 H9A 111.1 . . ?
C10 C9 H9B 111.1 . . ?
H9A C9 H9B 109.1 . . ?
C16 C17 H17 119.3 . . ?
C18 C17 C16 121.4(12) . . ?
C18 C17 H17 119.3 . . ?

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 -177.8(9) . . . . ?
O3 C27 C12 C11 61.4(9) . . . . ?
O3 C27 C12 C13 -52.8(9) . . . . ?
O3 C27 C12 C21 -178.2(7) . . . . ?
O3 C27 N2 C26 177.6(8) . . . . ?
C11 N1 C10 O1 170.7(9) . . . . ?
C11 N1 C10 C9 -9.2(10) . . . . ?
C11 C12 C13 C7 6.8(7) . . . . ?
C11 C12 C13 C14 133.3(7) . . . . ?
C11 C12 C21 C26 113.7(6) . . . . ?
C11 C12 C21 C22 -67.0(10) . . . . ?
C11 C8 C9 C10 27.9(10) . . . . ?
N1 C11 C12 C27 150.4(6) . . . . ?
N1 C11 C12 C13 -95.1(7) . . . . ?
N1 C11 C12 C21 38.7(8) . . . . ?
N1 C11 C8 C7 86.5(7) . . . . ?
N1 C11 C8 C9 -32.5(8) . . . . ?
N1 C10 C9 C8 -12.2(10) . . . . ?
C27 C12 C13 C7 120.3(6) . . . . ?
C27 C12 C13 C14 -113.3(7) . . . . ?
C27 C12 C21 C26 -0.3(7) . . . . ?
C27 C12 C21 C22 179.0(7) . . . . ?
C27 N2 C26 C21 1.9(9) . . . . ?
C27 N2 C26 C25 -178.6(8) . . . . ?
O1 C10 C9 C8 167.8(10) . . . . ?
C12 C11 N1 C10 140.6(7) . . . . ?
C12 C11 C8 C7 -31.9(8) . . . . ?
C12 C11 C8 C9 -150.9(7) . . . . ?
C12 C27 N2 C26 -2.0(8) . . . . ?
C12 C13 C7 C8 -25.4(7) . . . . ?
C12 C13 C7 C6 -149.0(6) . . . . ?
C12 C13 C14 O2 -107.0(9) . . . . ?
C12 C13 C14 C15 70.3(9) . . . . ?
N2 C27 C12 C11 -119.0(6) . . . . ?
N2 C27 C12 C13 126.9(6) . . . . ?
N2 C27 C12 C21 1.4(7) . . . . ?
N2 C26 C21 C12 -0.8(8) . . . . ?
N2 C26 C21 C22 179.8(7) . . . . ?
N2 C26 C25 C24 -178.0(9) . . . . ?
C13 C12 C21 C26 -118.1(6) . . . . ?
C13 C12 C21 C22 61.2(10) . . . . ?
C13 C7 C8 C11 35.4(8) . . . . ?
C13 C7 C8 C9 148.6(6) . . . . ?
C13 C7 C6 C1 -117.7(10) . . . . ?
C13 C7 C6 C5 61.5(11) . . . . ?
C13 C14 C15 C20 15.1(12) . . . . ?
C13 C14 C15 C16 -163.2(7) . . . . ?
O2 C14 C15 C20 -167.6(9) . . . . ?
O2 C14 C15 C16 14.2(13) . . . . ?
C7 C13 C14 O2 13.7(12) . . . . ?
C7 C13 C14 C15 -169.0(7) . . . . ?
C7 C8 C9 C10 -85.8(8) . . . . ?
C7 C6 C1 Br1 -0.7(14) . . . . ?
C7 C6 C1 C2 179.6(10) . . . . ?
C7 C6 C5 C4 178.1(9) . . . . ?
C14 C13 C7 C8 -150.6(6) . . . . ?
C14 C13 C7 C6 85.9(8) . . . . ?
C14 C15 C20 C19 -177.9(8) . . . . ?
C14 C15 C16 C17 179.2(9) . . . . ?
C8 C11 N1 C10 26.4(8) . . . . ?
C8 C11 C12 C27 -99.1(6) . . . . ?
C8 C11 C12 C13 15.3(7) . . . . ?
C8 C11 C12 C21 149.2(6) . . . . ?
C8 C7 C6 C1 123.9(10) . . . . ?
C8 C7 C6 C5 -56.9(10) . . . . ?
C6 C7 C8 C11 160.2(6) . . . . ?
C6 C7 C8 C9 -86.5(8) . . . . ?
C6 C1 C2 C3 1.9(18) . . . . ?
C6 C5 C4 C3 2.6(17) . . . . ?
C21 C12 C13 C7 -124.9(7) . . . . ?
C21 C12 C13 C14 1.5(9) . . . . ?
C21 C26 C25 C24 1.6(13) . . . . ?
C21 C22 C23 C24 -1.6(14) . . . . ?
C15 C20 C19 C18 -1.3(15) . . . . ?
C15 C16 C17 C18 -1.3(17) . . . . ?
C1 C6 C5 C4 -2.7(15) . . . . ?
C1 C2 C3 C4 -2.0(18) . . . . ?
C20 C15 C16 C17 0.9(13) . . . . ?
C20 C19 C18 C17 0.9(17) . . . . ?
C25 C26 C21 C12 179.6(7) . . . . ?
C25 C26 C21 C22 0.2(11) . . . . ?
C25 C24 C23 C22 3.5(17) . . . . ?
C23 C22 C21 C12 -179.5(8) . . . . ?
C23 C22 C21 C26 -0.2(11) . . . . ?
C23 C24 C25 C26 -3.4(16) . . . . ?
C5 C6 C1 Br1 -179.9(8) . . . . ?
C5 C6 C1 C2 0.4(15) . . . . ?
C5 C4 C3 C2 -0.1(18) . . . . ?
C16 C15 C20 C19 0.4(12) . . . . ?
C19 C18 C17 C16 0.3(19) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
