# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2022

####################################################################### 
# 
# 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_a
_database_code_depnum_ccdc_archive 'CCDC 2131456'
loop_
_audit_author_name
_audit_author_address
'Jiangtao Sun'
;Changzhou University
China
;
_audit_update_record             
;
2021-12-29 deposited with the CCDC.	2022-01-18 downloaded from the CCDC.
;
_audit_creation_date             2020-09-23
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C25 H24 Br N O3'
_chemical_formula_sum            'C25 H24 Br N O3'
_chemical_formula_weight         466.36
_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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   10.6644(6)
_cell_length_b                   11.9643(6)
_cell_length_c                   19.4199(9)
_cell_angle_alpha                75.708(2)
_cell_angle_beta                 85.239(2)
_cell_angle_gamma                70.225(2)
_cell_volume                     2259.5(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6347
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      26.933
_cell_measurement_theta_min      2.257
_shelx_estimated_absorpt_T_max   0.837
_shelx_estimated_absorpt_T_min   0.809
_exptl_absorpt_coefficient_mu    1.845
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5741
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1492 before and 0.0664 after correction.
The Ratio of minimum to maximum transmission is 0.7700.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.371
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             960
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0571
_diffrn_reflns_av_unetI/netI     0.0868
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            21000
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.504
_diffrn_reflns_theta_min         1.921
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.991
_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_source_current           40.0
_diffrn_source_power             2.0
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                7434
_reflns_number_total             10274
_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 v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_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 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.499
_refine_diff_density_min         -0.858
_refine_diff_density_rms         0.081
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     547
_refine_ls_number_reflns         10274
_refine_ls_number_restraints     18
_refine_ls_R_factor_all          0.0823
_refine_ls_R_factor_gt           0.0563
_refine_ls_restrained_S_all      1.045
_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)+(0.0487P)²+2.0627P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1399
_refine_ls_wR_factor_ref         0.1511
_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. Rigid body (RIGU) restrains
 C47, C49, C48, C50
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
3.a Ternary CH refined with riding coordinates:
 C15(H15), C40(H40)
3.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C9(H9), C10(H10), C11(H11), C12(H12),
 C13(H13), C14(H14), C17(H17), C18(H18), C20(H20), C26(H26), C27(H27), C28(H28),
  C29(H29), C30(H30), C34(H34), C35(H35), C36(H36), C37(H37), C38(H38),
 C39(H39), C42(H42), C43(H43), C45(H45)
3.c Idealised Me refined as rotating group:
 C23(H23A,H23B,H23C), C24(H24A,H24B,H24C), C25(H25A,H25B,H25C), C48(H48A,H48B,
 H48C), C49(H49A,H49B,H49C), C50(H50A,H50B,H50C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.18974(4) 0.44093(3) 0.62826(2) 0.04572(13) Uani 1 1 d . . . . .
O1 O 0.5083(3) -0.0808(2) 0.73280(15) 0.0444(7) Uani 1 1 d . . . . .
O2 O 0.5214(3) 0.1535(2) 0.84288(11) 0.0331(6) Uani 1 1 d . . . . .
O3 O 0.7457(3) 0.0861(2) 0.82941(11) 0.0315(5) Uani 1 1 d . . . . .
N1 N 0.4844(3) 0.1219(2) 0.71137(13) 0.0237(6) Uani 1 1 d . . . . .
C1 C 0.9885(4) 0.1154(3) 0.56193(16) 0.0304(8) Uani 1 1 d . . . . .
H1 H 1.010967 0.031764 0.566305 0.037 Uiso 1 1 calc R U . . .
C2 C 1.0537(4) 0.1819(4) 0.51157(17) 0.0399(9) Uani 1 1 d . . . . .
H2 H 1.119826 0.142444 0.483099 0.048 Uiso 1 1 calc R U . . .
C3 C 1.0195(4) 0.3065(3) 0.50416(18) 0.0413(9) Uani 1 1 d . . . . .
H3 H 1.061530 0.351266 0.470038 0.050 Uiso 1 1 calc R U . . .
C4 C 0.9235(4) 0.3641(3) 0.54722(18) 0.0365(8) Uani 1 1 d . . . . .
H4 H 0.901194 0.447807 0.542359 0.044 Uiso 1 1 calc R U . . .
C5 C 0.8593(4) 0.2977(3) 0.59818(17) 0.0306(7) Uani 1 1 d . . . . .
H5 H 0.795265 0.337489 0.627442 0.037 Uiso 1 1 calc R U . . .
C6 C 0.8903(3) 0.1723(3) 0.60567(15) 0.0244(7) Uani 1 1 d . . . . .
C7 C 0.8172(3) 0.1004(3) 0.65639(14) 0.0228(6) Uani 1 1 d . . . . .
C8 C 0.8831(4) -0.0345(3) 0.67577(14) 0.0253(7) Uani 1 1 d . . . . .
C9 C 1.0022(4) -0.0843(3) 0.71230(19) 0.0399(9) Uani 1 1 d . . . . .
H9 H 1.039511 -0.032992 0.725756 0.048 Uiso 1 1 calc R U . . .
C10 C 1.0667(5) -0.2084(4) 0.7292(2) 0.0590(13) Uani 1 1 d . . . . .
H10 H 1.147278 -0.240348 0.753622 0.071 Uiso 1 1 calc R U . . .
C11 C 1.0118(5) -0.2854(3) 0.7098(2) 0.0558(13) Uani 1 1 d . . . . .
H11 H 1.055327 -0.369315 0.721187 0.067 Uiso 1 1 calc R U . . .
C12 C 0.8946(5) -0.2387(3) 0.6744(2) 0.0460(12) Uani 1 1 d . . . . .
H12 H 0.858159 -0.291081 0.661449 0.055 Uiso 1 1 calc R U . . .
C13 C 0.8274(4) -0.1128(3) 0.65681(17) 0.0324(8) Uani 1 1 d . . . . .
H13 H 0.746461 -0.081511 0.632774 0.039 Uiso 1 1 calc R U . . .
C14 C 0.6996(4) 0.1558(3) 0.68278(15) 0.0253(7) Uani 1 1 d . . . . .
H14 H 0.663343 0.240166 0.667296 0.030 Uiso 1 1 calc R U . . .
C15 C 0.6214(3) 0.0909(3) 0.73600(15) 0.0234(7) Uani 1 1 d . . . . .
H15 H 0.665170 0.002918 0.740804 0.028 Uiso 1 1 calc R U . . .
C16 C 0.4367(4) 0.0261(3) 0.71111(17) 0.0301(7) Uani 1 1 d . . . . .
C17 C 0.3041(4) 0.0641(3) 0.68376(19) 0.0372(8) Uani 1 1 d . . . . .
H17 H 0.266787 0.004743 0.682440 0.045 Uiso 1 1 calc R U . . .
C18 C 0.2312(4) 0.1837(3) 0.65969(18) 0.0366(8) Uani 1 1 d . . . . .
H18 H 0.145699 0.205792 0.641841 0.044 Uiso 1 1 calc R U . . .
C19 C 0.2869(4) 0.2735(3) 0.66224(16) 0.0302(7) Uani 1 1 d . . . . .
C20 C 0.4101(4) 0.2425(3) 0.68812(15) 0.0274(7) Uani 1 1 d . . . . .
H20 H 0.445086 0.303030 0.690262 0.033 Uiso 1 1 calc R U . . .
C21 C 0.6197(4) 0.1168(3) 0.80985(16) 0.0250(7) Uani 1 1 d . . . . .
C22 C 0.7825(4) 0.1086(3) 0.89539(17) 0.0344(8) Uani 1 1 d . . . . .
C23 C 0.9309(5) 0.0739(5) 0.8891(3) 0.0587(12) Uani 1 1 d . . . . .
H23A H 0.968058 -0.010648 0.887668 0.088 Uiso 1 1 calc R U . . .
H23B H 0.966107 0.086747 0.929293 0.088 Uiso 1 1 calc R U . . .
H23C H 0.953641 0.123342 0.846252 0.088 Uiso 1 1 calc R U . . .
C24 C 0.7181(5) 0.2418(3) 0.89616(19) 0.0467(11) Uani 1 1 d . . . . .
H24A H 0.735629 0.291519 0.851988 0.070 Uiso 1 1 calc R U . . .
H24B H 0.754037 0.258753 0.934632 0.070 Uiso 1 1 calc R U . . .
H24C H 0.623601 0.259780 0.902346 0.070 Uiso 1 1 calc R U . . .
C25 C 0.7413(5) 0.0253(3) 0.95900(19) 0.0478(11) Uani 1 1 d . . . . .
H25A H 0.646485 0.043518 0.958360 0.072 Uiso 1 1 calc R U . . .
H25B H 0.766502 0.038091 1.002009 0.072 Uiso 1 1 calc R U . . .
H25C H 0.784886 -0.058307 0.956804 0.072 Uiso 1 1 calc R U . . .
Br2 Br 0.22365(5) 0.74264(4) 0.90640(2) 0.05312(14) Uani 1 1 d . . . . .
O4 O 0.5654(3) 0.4260(2) 0.72500(12) 0.0344(6) Uani 1 1 d . . . . .
O5 O 0.7113(3) 0.6092(2) 0.61642(12) 0.0402(6) Uani 1 1 d . . . . .
O6 O 0.4915(3) 0.6986(2) 0.63381(11) 0.0318(5) Uani 1 1 d . . . . .
N2 N 0.5132(3) 0.5915(2) 0.77243(12) 0.0233(6) Uani 1 1 d . . . . .
C26 C 1.0296(4) 0.3579(3) 0.81105(18) 0.0380(9) Uani 1 1 d . . . . .
H26 H 1.005733 0.364841 0.764808 0.046 Uiso 1 1 calc R U . . .
C27 C 1.1505(4) 0.2756(3) 0.83764(19) 0.0423(9) Uani 1 1 d . . . . .
H27 H 1.206330 0.227249 0.809159 0.051 Uiso 1 1 calc R U . . .
C28 C 1.1902(4) 0.2635(3) 0.90542(18) 0.0371(8) Uani 1 1 d . . . . .
H28 H 1.272431 0.208269 0.922701 0.045 Uiso 1 1 calc R U . . .
C29 C 1.1062(4) 0.3345(3) 0.94704(19) 0.0414(9) Uani 1 1 d . . . . .
H29 H 1.131464 0.326943 0.993105 0.050 Uiso 1 1 calc R U . . .
C30 C 0.9848(4) 0.4168(3) 0.92134(18) 0.0371(8) Uani 1 1 d . . . . .
H30 H 0.929730 0.464081 0.950529 0.045 Uiso 1 1 calc R U . . .
C31 C 0.9421(4) 0.4312(3) 0.85242(15) 0.0260(7) Uani 1 1 d . . . . .
C32 C 0.8110(4) 0.5200(3) 0.82594(15) 0.0249(7) Uani 1 1 d . . . . .
C33 C 0.7324(4) 0.6006(3) 0.87329(15) 0.0257(7) Uani 1 1 d . . . . .
C34 C 0.6653(4) 0.5549(3) 0.93200(17) 0.0314(8) Uani 1 1 d . . . . .
H34 H 0.672755 0.472659 0.943173 0.038 Uiso 1 1 calc R U . . .
C35 C 0.5874(4) 0.6305(3) 0.97399(17) 0.0363(8) Uani 1 1 d . . . . .
H35 H 0.543724 0.598577 1.013374 0.044 Uiso 1 1 calc R U . . .
C36 C 0.5742(4) 0.7521(3) 0.95793(18) 0.0411(9) Uani 1 1 d . . . . .
H36 H 0.520598 0.802920 0.985766 0.049 Uiso 1 1 calc R U . . .
C37 C 0.6411(5) 0.7984(3) 0.90013(18) 0.0408(9) Uani 1 1 d . . . . .
H37 H 0.632392 0.880917 0.889108 0.049 Uiso 1 1 calc R U . . .
C38 C 0.7217(4) 0.7230(3) 0.85813(16) 0.0339(8) Uani 1 1 d . . . . .
H38 H 0.768145 0.754618 0.819999 0.041 Uiso 1 1 calc R U . . .
C39 C 0.7606(4) 0.5299(3) 0.76279(15) 0.0259(7) Uani 1 1 d . . . . .
H39 H 0.810164 0.477277 0.734891 0.031 Uiso 1 1 calc R U . . .
C40 C 0.6294(4) 0.6204(3) 0.73457(15) 0.0252(7) Uani 1 1 d . . . . .
H40 H 0.626123 0.699139 0.742461 0.030 Uiso 1 1 calc R U . . .
C41 C 0.4916(4) 0.4872(3) 0.76501(16) 0.0272(7) Uani 1 1 d . . . . .
C42 C 0.3830(4) 0.4595(3) 0.80573(18) 0.0343(8) Uani 1 1 d . . . . .
H42 H 0.364867 0.389637 0.803792 0.041 Uiso 1 1 calc R U . . .
C43 C 0.3063(4) 0.5328(3) 0.84695(18) 0.0351(8) Uani 1 1 d . . . . .
H43 H 0.236331 0.513149 0.872931 0.042 Uiso 1 1 calc R U . . .
C44 C 0.3325(4) 0.6384(3) 0.85041(16) 0.0320(8) Uani 1 1 d . . . . .
C45 C 0.4339(4) 0.6670(3) 0.81289(16) 0.0292(7) Uani 1 1 d . . . . .
H45 H 0.450066 0.737960 0.814493 0.035 Uiso 1 1 calc R U . . .
C46 C 0.6162(4) 0.6381(3) 0.65432(16) 0.0280(7) Uani 1 1 d . . . . .
C47 C 0.4532(5) 0.7385(3) 0.55773(17) 0.0414(8) Uani 1 1 d . . . . .
C48 C 0.4821(5) 0.6284(4) 0.5267(2) 0.0592(12) Uani 1 1 d . . . . .
H48A H 0.576606 0.592768 0.521447 0.089 Uiso 1 1 calc R U . . .
H48B H 0.439959 0.652917 0.481077 0.089 Uiso 1 1 calc R U . . .
H48C H 0.448106 0.569369 0.557872 0.089 Uiso 1 1 calc R U . . .
C49 C 0.3037(5) 0.8013(5) 0.5617(3) 0.0735(14) Uani 1 1 d . . . . .
H49A H 0.263808 0.744914 0.590826 0.110 Uiso 1 1 calc R U . . .
H49B H 0.266397 0.828023 0.514773 0.110 Uiso 1 1 calc R U . . .
H49C H 0.286580 0.870461 0.582020 0.110 Uiso 1 1 calc R U . . .
C50 C 0.5233(6) 0.8255(5) 0.5183(2) 0.0695(13) Uani 1 1 d . . . . .
H50A H 0.512120 0.887886 0.543549 0.104 Uiso 1 1 calc R U . . .
H50B H 0.485999 0.862495 0.471531 0.104 Uiso 1 1 calc R U . . .
H50C H 0.616496 0.781698 0.514712 0.104 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 C19 1.892(3) . ?
O1 C16 1.234(4) . ?
O2 C21 1.191(4) . ?
O3 C21 1.330(4) . ?
O3 C22 1.481(4) . ?
N1 C15 1.470(4) . ?
N1 C16 1.403(4) . ?
N1 C20 1.371(4) . ?
C1 H1 0.9300 . ?
C1 C2 1.396(5) . ?
C1 C6 1.391(4) . ?
C2 H2 0.9300 . ?
C2 C3 1.382(5) . ?
C3 H3 0.9300 . ?
C3 C4 1.374(5) . ?
C4 H4 0.9300 . ?
C4 C5 1.395(5) . ?
C5 H5 0.9300 . ?
C5 C6 1.395(4) . ?
C6 C7 1.492(4) . ?
C7 C8 1.489(4) . ?
C7 C14 1.332(4) . ?
C8 C9 1.378(5) . ?
C8 C13 1.396(5) . ?
C9 H9 0.9300 . ?
C9 C10 1.375(5) . ?
C10 H10 0.9300 . ?
C10 C11 1.381(7) . ?
C11 H11 0.9300 . ?
C11 C12 1.352(7) . ?
C12 H12 0.9300 . ?
C12 C13 1.399(5) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
C14 C15 1.505(4) . ?
C15 H15 0.9800 . ?
C15 C21 1.538(4) . ?
C16 C17 1.435(5) . ?
C17 H17 0.9300 . ?
C17 C18 1.360(5) . ?
C18 H18 0.9300 . ?
C18 C19 1.404(5) . ?
C19 C20 1.343(5) . ?
C20 H20 0.9300 . ?
C22 C23 1.497(6) . ?
C22 C24 1.511(5) . ?
C22 C25 1.520(5) . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?
Br2 C44 1.888(3) . ?
O4 C41 1.245(4) . ?
O5 C46 1.206(4) . ?
O6 C46 1.321(4) . ?
O6 C47 1.482(4) . ?
N2 C40 1.485(4) . ?
N2 C41 1.386(4) . ?
N2 C45 1.367(4) . ?
C26 H26 0.9300 . ?
C26 C27 1.379(5) . ?
C26 C31 1.398(5) . ?
C27 H27 0.9300 . ?
C27 C28 1.375(5) . ?
C28 H28 0.9300 . ?
C28 C29 1.372(5) . ?
C29 H29 0.9300 . ?
C29 C30 1.377(5) . ?
C30 H30 0.9300 . ?
C30 C31 1.401(5) . ?
C31 C32 1.481(5) . ?
C32 C33 1.497(4) . ?
C32 C39 1.342(4) . ?
C33 C34 1.390(4) . ?
C33 C38 1.387(4) . ?
C34 H34 0.9300 . ?
C34 C35 1.385(5) . ?
C35 H35 0.9300 . ?
C35 C36 1.370(5) . ?
C36 H36 0.9300 . ?
C36 C37 1.380(5) . ?
C37 H37 0.9300 . ?
C37 C38 1.393(5) . ?
C38 H38 0.9300 . ?
C39 H39 0.9300 . ?
C39 C40 1.497(5) . ?
C40 H40 0.9800 . ?
C40 C46 1.532(4) . ?
C41 C42 1.433(5) . ?
C42 H42 0.9300 . ?
C42 C43 1.353(5) . ?
C43 H43 0.9300 . ?
C43 C44 1.401(5) . ?
C44 C45 1.347(5) . ?
C45 H45 0.9300 . ?
C47 C48 1.511(5) . ?
C47 C49 1.519(7) . ?
C47 C50 1.506(6) . ?
C48 H48A 0.9600 . ?
C48 H48B 0.9600 . ?
C48 H48C 0.9600 . ?
C49 H49A 0.9600 . ?
C49 H49B 0.9600 . ?
C49 H49C 0.9600 . ?
C50 H50A 0.9600 . ?
C50 H50B 0.9600 . ?
C50 H50C 0.9600 . ?

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
C21 O3 C22 122.3(3) . . ?
C16 N1 C15 118.3(3) . . ?
C20 N1 C15 118.8(3) . . ?
C20 N1 C16 122.9(3) . . ?
C2 C1 H1 119.5 . . ?
C6 C1 H1 119.5 . . ?
C6 C1 C2 121.0(3) . . ?
C1 C2 H2 120.1 . . ?
C3 C2 C1 119.8(3) . . ?
C3 C2 H2 120.1 . . ?
C2 C3 H3 120.0 . . ?
C4 C3 C2 120.0(3) . . ?
C4 C3 H3 120.0 . . ?
C3 C4 H4 119.8 . . ?
C3 C4 C5 120.4(3) . . ?
C5 C4 H4 119.8 . . ?
C4 C5 H5 119.7 . . ?
C4 C5 C6 120.6(3) . . ?
C6 C5 H5 119.7 . . ?
C1 C6 C5 118.2(3) . . ?
C1 C6 C7 119.9(3) . . ?
C5 C6 C7 121.8(3) . . ?
C8 C7 C6 116.6(3) . . ?
C14 C7 C6 120.9(3) . . ?
C14 C7 C8 122.5(3) . . ?
C9 C8 C7 120.1(3) . . ?
C9 C8 C13 118.7(3) . . ?
C13 C8 C7 121.2(3) . . ?
C8 C9 H9 119.4 . . ?
C10 C9 C8 121.2(4) . . ?
C10 C9 H9 119.4 . . ?
C9 C10 H10 120.1 . . ?
C9 C10 C11 119.9(4) . . ?
C11 C10 H10 120.1 . . ?
C10 C11 H11 120.0 . . ?
C12 C11 C10 120.0(4) . . ?
C12 C11 H11 120.0 . . ?
C11 C12 H12 119.5 . . ?
C11 C12 C13 120.9(4) . . ?
C13 C12 H12 119.5 . . ?
C8 C13 C12 119.3(4) . . ?
C8 C13 H13 120.4 . . ?
C12 C13 H13 120.4 . . ?
C7 C14 H14 117.8 . . ?
C7 C14 C15 124.4(3) . . ?
C15 C14 H14 117.8 . . ?
N1 C15 C14 111.4(2) . . ?
N1 C15 H15 107.6 . . ?
N1 C15 C21 110.1(2) . . ?
C14 C15 H15 107.6 . . ?
C14 C15 C21 112.3(3) . . ?
C21 C15 H15 107.6 . . ?
O1 C16 N1 119.9(3) . . ?
O1 C16 C17 125.3(3) . . ?
N1 C16 C17 114.8(3) . . ?
C16 C17 H17 118.9 . . ?
C18 C17 C16 122.3(3) . . ?
C18 C17 H17 118.9 . . ?
C17 C18 H18 120.5 . . ?
C17 C18 C19 118.9(4) . . ?
C19 C18 H18 120.5 . . ?
C18 C19 Br1 120.3(3) . . ?
C20 C19 Br1 118.7(3) . . ?
C20 C19 C18 120.9(3) . . ?
N1 C20 H20 119.9 . . ?
C19 C20 N1 120.1(3) . . ?
C19 C20 H20 119.9 . . ?
O2 C21 O3 128.0(3) . . ?
O2 C21 C15 124.7(3) . . ?
O3 C21 C15 107.3(3) . . ?
O3 C22 C23 102.1(3) . . ?
O3 C22 C24 109.9(3) . . ?
O3 C22 C25 108.9(3) . . ?
C23 C22 C24 111.8(4) . . ?
C23 C22 C25 111.5(3) . . ?
C24 C22 C25 112.0(3) . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C22 C24 H24A 109.5 . . ?
C22 C24 H24B 109.5 . . ?
C22 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C22 C25 H25A 109.5 . . ?
C22 C25 H25B 109.5 . . ?
C22 C25 H25C 109.5 . . ?
H25A C25 H25B 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C46 O6 C47 121.7(3) . . ?
C41 N2 C40 117.4(2) . . ?
C45 N2 C40 119.4(3) . . ?
C45 N2 C41 123.2(3) . . ?
C27 C26 H26 119.4 . . ?
C27 C26 C31 121.1(3) . . ?
C31 C26 H26 119.4 . . ?
C26 C27 H27 119.3 . . ?
C28 C27 C26 121.3(3) . . ?
C28 C27 H27 119.3 . . ?
C27 C28 H28 120.7 . . ?
C29 C28 C27 118.7(4) . . ?
C29 C28 H28 120.7 . . ?
C28 C29 H29 119.6 . . ?
C28 C29 C30 120.7(3) . . ?
C30 C29 H29 119.6 . . ?
C29 C30 H30 119.1 . . ?
C29 C30 C31 121.8(3) . . ?
C31 C30 H30 119.1 . . ?
C26 C31 C30 116.4(3) . . ?
C26 C31 C32 122.7(3) . . ?
C30 C31 C32 120.9(3) . . ?
C31 C32 C33 117.2(3) . . ?
C39 C32 C31 123.2(3) . . ?
C39 C32 C33 119.6(3) . . ?
C34 C33 C32 120.5(3) . . ?
C38 C33 C32 120.6(3) . . ?
C38 C33 C34 118.9(3) . . ?
C33 C34 H34 119.7 . . ?
C35 C34 C33 120.6(3) . . ?
C35 C34 H34 119.7 . . ?
C34 C35 H35 119.8 . . ?
C36 C35 C34 120.5(3) . . ?
C36 C35 H35 119.8 . . ?
C35 C36 H36 120.3 . . ?
C35 C36 C37 119.5(3) . . ?
C37 C36 H36 120.3 . . ?
C36 C37 H37 119.7 . . ?
C36 C37 C38 120.7(3) . . ?
C38 C37 H37 119.7 . . ?
C33 C38 C37 119.9(3) . . ?
C33 C38 H38 120.1 . . ?
C37 C38 H38 120.1 . . ?
C32 C39 H39 118.0 . . ?
C32 C39 C40 124.0(3) . . ?
C40 C39 H39 118.0 . . ?
N2 C40 C39 113.3(2) . . ?
N2 C40 H40 106.8 . . ?
N2 C40 C46 110.4(3) . . ?
C39 C40 H40 106.8 . . ?
C39 C40 C46 112.3(3) . . ?
C46 C40 H40 106.8 . . ?
O4 C41 N2 119.2(3) . . ?
O4 C41 C42 125.6(3) . . ?
N2 C41 C42 115.2(3) . . ?
C41 C42 H42 119.2 . . ?
C43 C42 C41 121.5(3) . . ?
C43 C42 H42 119.2 . . ?
C42 C43 H43 120.1 . . ?
C42 C43 C44 119.9(3) . . ?
C44 C43 H43 120.1 . . ?
C43 C44 Br2 120.0(3) . . ?
C45 C44 Br2 119.8(3) . . ?
C45 C44 C43 120.1(3) . . ?
N2 C45 H45 120.0 . . ?
C44 C45 N2 120.0(3) . . ?
C44 C45 H45 120.0 . . ?
O5 C46 O6 126.7(3) . . ?
O5 C46 C40 122.5(3) . . ?
O6 C46 C40 110.5(3) . . ?
O6 C47 C48 109.8(3) . . ?
O6 C47 C49 101.8(3) . . ?
O6 C47 C50 110.0(3) . . ?
C48 C47 C49 110.2(4) . . ?
C50 C47 C48 112.4(4) . . ?
C50 C47 C49 112.0(4) . . ?
C47 C48 H48A 109.5 . . ?
C47 C48 H48B 109.5 . . ?
C47 C48 H48C 109.5 . . ?
H48A C48 H48B 109.5 . . ?
H48A C48 H48C 109.5 . . ?
H48B C48 H48C 109.5 . . ?
C47 C49 H49A 109.5 . . ?
C47 C49 H49B 109.5 . . ?
C47 C49 H49C 109.5 . . ?
H49A C49 H49B 109.5 . . ?
H49A C49 H49C 109.5 . . ?
H49B C49 H49C 109.5 . . ?
C47 C50 H50A 109.5 . . ?
C47 C50 H50B 109.5 . . ?
C47 C50 H50C 109.5 . . ?
H50A C50 H50B 109.5 . . ?
H50A C50 H50C 109.5 . . ?
H50B C50 H50C 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
Br1 C19 C20 N1 -178.3(2) . . . . ?
O1 C16 C17 C18 -179.0(3) . . . . ?
N1 C15 C21 O2 1.9(4) . . . . ?
N1 C15 C21 O3 179.5(2) . . . . ?
N1 C16 C17 C18 0.3(5) . . . . ?
C1 C2 C3 C4 1.2(6) . . . . ?
C1 C6 C7 C8 20.7(4) . . . . ?
C1 C6 C7 C14 -159.7(3) . . . . ?
C2 C1 C6 C5 -0.4(5) . . . . ?
C2 C1 C6 C7 176.8(3) . . . . ?
C2 C3 C4 C5 -0.5(6) . . . . ?
C3 C4 C5 C6 -0.8(6) . . . . ?
C4 C5 C6 C1 1.2(5) . . . . ?
C4 C5 C6 C7 -175.9(3) . . . . ?
C5 C6 C7 C8 -162.2(3) . . . . ?
C5 C6 C7 C14 17.3(5) . . . . ?
C6 C1 C2 C3 -0.8(6) . . . . ?
C6 C7 C8 C9 64.3(4) . . . . ?
C6 C7 C8 C13 -114.8(3) . . . . ?
C6 C7 C14 C15 -177.8(3) . . . . ?
C7 C8 C9 C10 -178.3(3) . . . . ?
C7 C8 C13 C12 178.2(3) . . . . ?
C7 C14 C15 N1 -126.8(3) . . . . ?
C7 C14 C15 C21 109.1(3) . . . . ?
C8 C7 C14 C15 1.7(5) . . . . ?
C8 C9 C10 C11 -0.4(6) . . . . ?
C9 C8 C13 C12 -1.0(5) . . . . ?
C9 C10 C11 C12 0.0(7) . . . . ?
C10 C11 C12 C13 -0.1(6) . . . . ?
C11 C12 C13 C8 0.6(5) . . . . ?
C13 C8 C9 C10 0.9(5) . . . . ?
C14 C7 C8 C9 -115.3(4) . . . . ?
C14 C7 C8 C13 65.6(4) . . . . ?
C14 C15 C21 O2 126.7(3) . . . . ?
C14 C15 C21 O3 -55.7(3) . . . . ?
C15 N1 C16 O1 1.7(4) . . . . ?
C15 N1 C16 C17 -177.7(3) . . . . ?
C15 N1 C20 C19 176.9(3) . . . . ?
C16 N1 C15 C14 128.0(3) . . . . ?
C16 N1 C15 C21 -106.7(3) . . . . ?
C16 N1 C20 C19 -1.4(4) . . . . ?
C16 C17 C18 C19 -0.6(5) . . . . ?
C17 C18 C19 Br1 179.2(3) . . . . ?
C17 C18 C19 C20 -0.2(5) . . . . ?
C18 C19 C20 N1 1.2(5) . . . . ?
C20 N1 C15 C14 -50.5(3) . . . . ?
C20 N1 C15 C21 74.8(3) . . . . ?
C20 N1 C16 O1 -179.9(3) . . . . ?
C20 N1 C16 C17 0.7(4) . . . . ?
C21 O3 C22 C23 -173.2(3) . . . . ?
C21 O3 C22 C24 -54.4(4) . . . . ?
C21 O3 C22 C25 68.7(4) . . . . ?
C22 O3 C21 O2 -7.9(5) . . . . ?
C22 O3 C21 C15 174.7(2) . . . . ?
Br2 C44 C45 N2 179.8(2) . . . . ?
O4 C41 C42 C43 -178.7(4) . . . . ?
N2 C40 C46 O5 -146.3(3) . . . . ?
N2 C40 C46 O6 39.9(3) . . . . ?
N2 C41 C42 C43 1.4(5) . . . . ?
C26 C27 C28 C29 0.7(6) . . . . ?
C26 C31 C32 C33 -174.7(3) . . . . ?
C26 C31 C32 C39 6.0(5) . . . . ?
C27 C26 C31 C30 0.5(5) . . . . ?
C27 C26 C31 C32 -179.5(3) . . . . ?
C27 C28 C29 C30 -0.4(6) . . . . ?
C28 C29 C30 C31 0.2(6) . . . . ?
C29 C30 C31 C26 -0.2(5) . . . . ?
C29 C30 C31 C32 179.8(3) . . . . ?
C30 C31 C32 C33 5.3(4) . . . . ?
C30 C31 C32 C39 -174.1(3) . . . . ?
C31 C26 C27 C28 -0.8(6) . . . . ?
C31 C32 C33 C34 -76.2(4) . . . . ?
C31 C32 C33 C38 105.9(4) . . . . ?
C31 C32 C39 C40 -178.9(3) . . . . ?
C32 C33 C34 C35 -177.0(3) . . . . ?
C32 C33 C38 C37 175.9(3) . . . . ?
C32 C39 C40 N2 -71.4(4) . . . . ?
C32 C39 C40 C46 162.6(3) . . . . ?
C33 C32 C39 C40 1.8(5) . . . . ?
C33 C34 C35 C36 0.6(6) . . . . ?
C34 C33 C38 C37 -2.1(6) . . . . ?
C34 C35 C36 C37 -1.1(6) . . . . ?
C35 C36 C37 C38 0.0(6) . . . . ?
C36 C37 C38 C33 1.6(6) . . . . ?
C38 C33 C34 C35 1.0(6) . . . . ?
C39 C32 C33 C34 103.2(4) . . . . ?
C39 C32 C33 C38 -74.8(5) . . . . ?
C39 C40 C46 O5 -18.8(4) . . . . ?
C39 C40 C46 O6 167.5(3) . . . . ?
C40 N2 C41 O4 -3.3(4) . . . . ?
C40 N2 C41 C42 176.6(3) . . . . ?
C40 N2 C45 C44 -176.5(3) . . . . ?
C41 N2 C40 C39 -66.9(3) . . . . ?
C41 N2 C40 C46 60.1(3) . . . . ?
C41 N2 C45 C44 2.9(5) . . . . ?
C41 C42 C43 C44 0.0(6) . . . . ?
C42 C43 C44 Br2 178.8(3) . . . . ?
C42 C43 C44 C45 -0.1(5) . . . . ?
C43 C44 C45 N2 -1.3(5) . . . . ?
C45 N2 C40 C39 112.6(3) . . . . ?
C45 N2 C40 C46 -120.4(3) . . . . ?
C45 N2 C41 O4 177.3(3) . . . . ?
C45 N2 C41 C42 -2.9(5) . . . . ?
C46 O6 C47 C48 62.7(5) . . . . ?
C46 O6 C47 C49 179.5(3) . . . . ?
C46 O6 C47 C50 -61.5(4) . . . . ?
C47 O6 C46 O5 0.6(5) . . . . ?
C47 O6 C46 C40 174.1(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
