# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_liujw_190322_3
_database_code_depnum_ccdc_archive 'CCDC 1911189'
_audit_update_record             
;
2019-10-12 deposited with the CCDC.	2019-11-08 downloaded from the CCDC.
;
_audit_creation_date             2019-03-25
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C26 H26 Br N3 O3'
_chemical_formula_sum            'C26 H26 Br N3 O3'
_chemical_formula_weight         508.41
_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 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           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                   14.9877(2)
_cell_length_b                   8.49500(10)
_cell_length_c                   19.3047(3)
_cell_angle_alpha                90
_cell_angle_beta                 111.380(2)
_cell_angle_gamma                90
_cell_volume                     2288.74(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9901
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      76.2160
_cell_measurement_theta_min      3.1670
_shelx_estimated_absorpt_T_max   0.772
_shelx_estimated_absorpt_T_min   0.495
_exptl_absorpt_coefficient_mu    2.724
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.50410
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
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    1.475
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1048
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0427
_diffrn_reflns_av_unetI/netI     0.0392
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.938
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            15072
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.938
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.512
_diffrn_reflns_theta_min         3.167
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.938
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -99.00 -74.00   0.50    0.05    --  -46.62 -57.00  10.00   50
  2  ω    -63.00  26.00   0.50    0.05    --  -46.62  57.00 151.00  178
  3  ω    -24.00  45.00   0.50    0.05    --   46.62 -57.00  10.00  138
  4  ω     43.00 100.00   0.50    0.05    --   46.62  57.00 151.00  114
  5  ω   -170.00 -88.00   0.50    0.05    -- -100.00 -57.00  10.00  164
  6  ω   -116.00 -27.00   0.50    0.05    -- -100.00  57.00 151.00  178
  7  ω     42.00  68.00   0.50    0.05    --  107.00 -57.00  10.00   52
  8  ω    108.00 135.00   0.50    0.05    --  107.00  57.00 151.00   54
  9  ω   -117.00 -72.00   0.50    0.05    --  -46.62-125.00-180.00   90
 10  ω   -118.00 -72.00   0.50    0.05    --  -46.62-125.00 150.00   92
 11  ω   -137.00 -85.00   0.50    0.05    -- -100.00 -15.00 -90.00  104
 12  ω   -160.00-122.00   0.50    0.05    -- -100.00 -94.00  90.00   76
 13  ω   -117.00 -91.00   0.50    0.05    -- -100.00  61.00   0.00   52
 14  ω    -69.00 -35.00   0.50    0.05    -- -100.00  61.00   0.00   68
 15  ω   -115.00 -28.00   0.50    0.05    -- -100.00  30.00 150.00  174
 16  ω   -114.00 -40.00   0.50    0.05    -- -100.00  15.00 -30.00  148
 17  ω     47.00  73.00   0.50    0.05    --  107.00 -94.00-120.00   52
 18  ω     35.00 101.00   0.50    0.05    --  107.00 -94.00-150.00  132
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0604594000
_diffrn_orient_matrix_UB_12      -0.0200750000
_diffrn_orient_matrix_UB_13      0.0490541000
_diffrn_orient_matrix_UB_21      0.0722153000
_diffrn_orient_matrix_UB_22      -0.1223782000
_diffrn_orient_matrix_UB_23      0.0477436000
_diffrn_orient_matrix_UB_31      0.0575416000
_diffrn_orient_matrix_UB_32      0.1324602000
_diffrn_orient_matrix_UB_33      0.0514919000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4067
_reflns_number_total             4519
_reflns_odcompleteness_completeness 99.89
_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 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.888
_refine_diff_density_min         -0.792
_refine_diff_density_rms         0.085
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.098
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     299
_refine_ls_number_reflns         4519
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0483
_refine_ls_R_factor_gt           0.0435
_refine_ls_restrained_S_all      1.098
_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)+(0.0602P)²+2.2579P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1140
_refine_ls_wR_factor_ref         0.1172
_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
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C2(H2), C14(H14)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C10(H10A,H10B), C17(H17A,H17B)
2.c Aromatic/amide H refined with riding coordinates:
 N11(H11), N20(H20), C29(H29), C31(H31), C25(H25), C33(H33), C4(H4), C32(H32),
 C22(H22), C30(H30), C7(H7), C5(H5), C6(H6), C23(H23), C24(H24)
2.d Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C)
;
_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
Br27 Br 0.29377(2) 0.93361(3) 0.79375(2) 0.02883(12) Uani 1 1 d . . . . .
O13 O 0.22002(13) 0.9989(2) 0.58123(10) 0.0259(4) Uani 1 1 d . . . . .
O16 O 0.37147(14) 0.7358(2) 0.58341(10) 0.0309(4) Uani 1 1 d . . . . .
O19 O 0.31732(15) 0.5128(2) 0.51814(11) 0.0341(5) Uani 1 1 d . . . . .
N1 N 0.12712(14) 0.7223(2) 0.56969(11) 0.0209(4) Uani 1 1 d . . . . .
N11 N 0.14484(15) 0.7912(2) 0.50988(11) 0.0227(4) Uani 1 1 d . . . . .
H11 H 0.127102 0.745208 0.467312 0.027 Uiso 1 1 calc R . . . .
N20 N 0.29192(14) 0.6703(2) 0.68546(11) 0.0213(4) Uani 1 1 d . . . . .
H20 H 0.247070 0.732923 0.685975 0.026 Uiso 1 1 calc R . . . .
C3 C 0.11296(18) 0.4578(3) 0.62100(13) 0.0205(5) Uani 1 1 d . . . . .
C28 C 0.20521(17) 0.9999(3) 0.45401(14) 0.0218(5) Uani 1 1 d . . . . .
C2 C 0.16247(18) 0.5590(3) 0.58067(14) 0.0200(5) Uani 1 1 d . . . . .
H2 H 0.150455 0.512281 0.531672 0.024 Uiso 1 1 calc R . . . .
C12 C 0.19091(18) 0.9331(3) 0.52081(15) 0.0216(5) Uani 1 1 d . . . . .
C15 C 0.32300(18) 0.6007(3) 0.56851(14) 0.0236(5) Uani 1 1 d . . . . .
C29 C 0.22156(17) 1.1622(3) 0.45375(14) 0.0230(5) Uani 1 1 d . . . . .
H29 H 0.221477 1.223946 0.493520 0.028 Uiso 1 1 calc R . . . .
C14 C 0.27274(18) 0.5651(3) 0.62355(14) 0.0208(5) Uani 1 1 d . . . . .
H14 H 0.293023 0.459697 0.643861 0.025 Uiso 1 1 calc R . . . .
C31 C 0.23856(18) 1.1392(3) 0.33498(14) 0.0270(5) Uani 1 1 d . . . . .
H31 H 0.249220 1.185888 0.295103 0.032 Uiso 1 1 calc R . . . .
C25 C 0.47802(19) 0.7967(3) 0.86240(15) 0.0275(5) Uani 1 1 d . . . . .
H25 H 0.485295 0.872155 0.898952 0.033 Uiso 1 1 calc R . . . .
C33 C 0.20720(18) 0.9079(3) 0.39437(14) 0.0239(5) Uani 1 1 d . . . . .
H33 H 0.197693 0.799724 0.394415 0.029 Uiso 1 1 calc R . . . .
C21 C 0.37874(17) 0.6761(3) 0.74422(14) 0.0212(5) Uani 1 1 d . . . . .
C9 C 0.02127(18) 0.6923(3) 0.63770(15) 0.0259(5) Uani 1 1 d . . . . .
H9A H 0.065904 0.749726 0.679385 0.031 Uiso 1 1 calc R . . . .
H9B H -0.042975 0.710624 0.636892 0.031 Uiso 1 1 calc R . . . .
C4 C 0.13390(18) 0.2978(3) 0.62888(14) 0.0239(5) Uani 1 1 d . . . . .
H4 H 0.180146 0.257155 0.612240 0.029 Uiso 1 1 calc R . . . .
C8 C 0.04373(18) 0.5194(3) 0.64674(14) 0.0231(5) Uani 1 1 d . . . . .
C32 C 0.22342(19) 0.9787(3) 0.33515(15) 0.0266(5) Uani 1 1 d . . . . .
H32 H 0.224109 0.917673 0.295347 0.032 Uiso 1 1 calc R . . . .
C22 C 0.45437(19) 0.5720(3) 0.75284(16) 0.0260(5) Uani 1 1 d . . . . .
H22 H 0.447488 0.495395 0.716847 0.031 Uiso 1 1 calc R . . . .
C30 C 0.23783(18) 1.2309(3) 0.39447(15) 0.0263(5) Uani 1 1 d . . . . .
H30 H 0.248315 1.338782 0.394377 0.032 Uiso 1 1 calc R . . . .
C7 C -0.00366(19) 0.4170(3) 0.67813(15) 0.0274(6) Uani 1 1 d . . . . .
H7 H -0.050349 0.456605 0.694539 0.033 Uiso 1 1 calc R . . . .
C10 C 0.02881(17) 0.7505(3) 0.56531(14) 0.0240(5) Uani 1 1 d . . . . .
H10A H -0.016118 0.694241 0.523330 0.029 Uiso 1 1 calc R . . . .
H10B H 0.014030 0.861957 0.558841 0.029 Uiso 1 1 calc R . . . .
C5 C 0.08698(19) 0.1979(3) 0.66111(14) 0.0275(5) Uani 1 1 d . . . . .
H5 H 0.102150 0.091350 0.666436 0.033 Uiso 1 1 calc R . . . .
C26 C 0.39355(18) 0.7879(3) 0.80132(14) 0.0230(5) Uani 1 1 d . . . . .
C6 C 0.01717(19) 0.2577(3) 0.68544(14) 0.0287(6) Uani 1 1 d . . . . .
H6 H -0.015307 0.191165 0.706470 0.034 Uiso 1 1 calc R . . . .
C23 C 0.5393(2) 0.5806(3) 0.81387(16) 0.0300(6) Uani 1 1 d . . . . .
H23 H 0.588564 0.510378 0.817891 0.036 Uiso 1 1 calc R . . . .
C24 C 0.55205(19) 0.6922(3) 0.86896(15) 0.0293(6) Uani 1 1 d . . . . .
H24 H 0.609278 0.697164 0.909744 0.035 Uiso 1 1 calc R . . . .
C17 C 0.4191(2) 0.7877(4) 0.53382(17) 0.0389(7) Uani 1 1 d . . . . .
H17A H 0.405746 0.898339 0.522166 0.047 Uiso 1 1 calc R . . . .
H17B H 0.394773 0.728648 0.487696 0.047 Uiso 1 1 calc R . . . .
C18 C 0.5230(2) 0.7639(5) 0.5692(2) 0.0507(9) Uani 1 1 d . . . . .
H18A H 0.554609 0.812744 0.539538 0.076 Uiso 1 1 calc GR . . . .
H18B H 0.536796 0.653199 0.573222 0.076 Uiso 1 1 calc GR . . . .
H18C H 0.545500 0.810207 0.617892 0.076 Uiso 1 1 calc GR . . . .


_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
Br27 C26 1.906(2) . ?
O13 C12 1.222(3) . ?
O16 C15 1.333(3) . ?
O16 C17 1.456(3) . ?
O19 C15 1.204(3) . ?
N1 N11 1.404(3) . ?
N1 C2 1.472(3) . ?
N1 C10 1.464(3) . ?
N11 H11 0.8600 . ?
N11 C12 1.366(3) . ?
N20 H20 0.8600 . ?
N20 C14 1.435(3) . ?
N20 C21 1.381(3) . ?
C3 C2 1.522(3) . ?
C3 C4 1.391(3) . ?
C3 C8 1.405(3) . ?
C28 C12 1.494(3) . ?
C28 C29 1.401(3) . ?
C28 C33 1.401(4) . ?
C2 H2 0.9800 . ?
C2 C14 1.556(4) . ?
C15 C14 1.540(3) . ?
C29 H29 0.9300 . ?
C29 C30 1.383(4) . ?
C14 H14 0.9800 . ?
C31 H31 0.9300 . ?
C31 C32 1.383(4) . ?
C31 C30 1.391(4) . ?
C25 H25 0.9300 . ?
C25 C26 1.382(4) . ?
C25 C24 1.390(4) . ?
C33 H33 0.9300 . ?
C33 C32 1.389(4) . ?
C21 C22 1.399(3) . ?
C21 C26 1.409(3) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 C8 1.503(4) . ?
C9 C10 1.525(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.386(4) . ?
C8 C7 1.393(4) . ?
C32 H32 0.9300 . ?
C22 H22 0.9300 . ?
C22 C23 1.386(4) . ?
C30 H30 0.9300 . ?
C7 H7 0.9300 . ?
C7 C6 1.385(4) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C5 H5 0.9300 . ?
C5 C6 1.390(4) . ?
C6 H6 0.9300 . ?
C23 H23 0.9300 . ?
C23 C24 1.385(4) . ?
C24 H24 0.9300 . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C17 C18 1.468(4) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 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
C15 O16 C17 118.6(2) . . ?
N11 N1 C2 110.20(18) . . ?
N11 N1 C10 111.86(19) . . ?
C10 N1 C2 117.66(19) . . ?
N1 N11 H11 120.7 . . ?
C12 N11 N1 118.5(2) . . ?
C12 N11 H11 120.7 . . ?
C14 N20 H20 118.3 . . ?
C21 N20 H20 118.3 . . ?
C21 N20 C14 123.3(2) . . ?
C4 C3 C2 118.4(2) . . ?
C4 C3 C8 119.4(2) . . ?
C8 C3 C2 122.1(2) . . ?
C29 C28 C12 117.2(2) . . ?
C29 C28 C33 119.4(2) . . ?
C33 C28 C12 123.4(2) . . ?
N1 C2 C3 112.87(19) . . ?
N1 C2 H2 108.2 . . ?
N1 C2 C14 107.59(18) . . ?
C3 C2 H2 108.2 . . ?
C3 C2 C14 111.6(2) . . ?
C14 C2 H2 108.2 . . ?
O13 C12 N11 122.4(2) . . ?
O13 C12 C28 122.4(2) . . ?
N11 C12 C28 115.2(2) . . ?
O16 C15 C14 112.7(2) . . ?
O19 C15 O16 125.5(2) . . ?
O19 C15 C14 121.8(2) . . ?
C28 C29 H29 119.9 . . ?
C30 C29 C28 120.1(2) . . ?
C30 C29 H29 119.9 . . ?
N20 C14 C2 108.36(19) . . ?
N20 C14 C15 116.9(2) . . ?
N20 C14 H14 107.3 . . ?
C2 C14 H14 107.3 . . ?
C15 C14 C2 109.3(2) . . ?
C15 C14 H14 107.3 . . ?
C32 C31 H31 120.0 . . ?
C32 C31 C30 120.0(2) . . ?
C30 C31 H31 120.0 . . ?
C26 C25 H25 120.1 . . ?
C26 C25 C24 119.7(2) . . ?
C24 C25 H25 120.1 . . ?
C28 C33 H33 120.1 . . ?
C32 C33 C28 119.8(2) . . ?
C32 C33 H33 120.1 . . ?
N20 C21 C22 123.7(2) . . ?
N20 C21 C26 119.9(2) . . ?
C22 C21 C26 116.3(2) . . ?
H9A C9 H9B 108.2 . . ?
C8 C9 H9A 109.8 . . ?
C8 C9 H9B 109.8 . . ?
C8 C9 C10 109.6(2) . . ?
C10 C9 H9A 109.8 . . ?
C10 C9 H9B 109.8 . . ?
C3 C4 H4 119.5 . . ?
C5 C4 C3 121.1(2) . . ?
C5 C4 H4 119.5 . . ?
C3 C8 C9 119.1(2) . . ?
C7 C8 C3 118.7(2) . . ?
C7 C8 C9 122.2(2) . . ?
C31 C32 C33 120.5(2) . . ?
C31 C32 H32 119.8 . . ?
C33 C32 H32 119.8 . . ?
C21 C22 H22 119.3 . . ?
C23 C22 C21 121.4(2) . . ?
C23 C22 H22 119.3 . . ?
C29 C30 C31 120.3(2) . . ?
C29 C30 H30 119.9 . . ?
C31 C30 H30 119.9 . . ?
C8 C7 H7 119.2 . . ?
C6 C7 C8 121.5(2) . . ?
C6 C7 H7 119.2 . . ?
N1 C10 C9 107.6(2) . . ?
N1 C10 H10A 110.2 . . ?
N1 C10 H10B 110.2 . . ?
C9 C10 H10A 110.2 . . ?
C9 C10 H10B 110.2 . . ?
H10A C10 H10B 108.5 . . ?
C4 C5 H5 120.1 . . ?
C4 C5 C6 119.7(2) . . ?
C6 C5 H5 120.1 . . ?
C25 C26 Br27 118.64(19) . . ?
C25 C26 C21 122.5(2) . . ?
C21 C26 Br27 118.82(19) . . ?
C7 C6 C5 119.5(2) . . ?
C7 C6 H6 120.3 . . ?
C5 C6 H6 120.3 . . ?
C22 C23 H23 119.5 . . ?
C24 C23 C22 121.0(2) . . ?
C24 C23 H23 119.5 . . ?
C25 C24 H24 120.5 . . ?
C23 C24 C25 119.0(3) . . ?
C23 C24 H24 120.5 . . ?
O16 C17 H17A 109.6 . . ?
O16 C17 H17B 109.6 . . ?
O16 C17 C18 110.1(3) . . ?
H17A C17 H17B 108.2 . . ?
C18 C17 H17A 109.6 . . ?
C18 C17 H17B 109.6 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 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
O16 C15 C14 N20 -5.8(3) . . . . ?
O16 C15 C14 C2 117.7(2) . . . . ?
O19 C15 C14 N20 174.2(2) . . . . ?
O19 C15 C14 C2 -62.2(3) . . . . ?
N1 N11 C12 O13 2.6(4) . . . . ?
N1 N11 C12 C28 -178.8(2) . . . . ?
N1 C2 C14 N20 47.6(2) . . . . ?
N1 C2 C14 C15 -80.8(2) . . . . ?
N11 N1 C2 C3 -157.0(2) . . . . ?
N11 N1 C2 C14 79.5(2) . . . . ?
N11 N1 C10 C9 -172.0(2) . . . . ?
N20 C21 C22 C23 -178.4(2) . . . . ?
N20 C21 C26 Br27 -2.2(3) . . . . ?
N20 C21 C26 C25 178.3(2) . . . . ?
C3 C2 C14 N20 -76.7(2) . . . . ?
C3 C2 C14 C15 154.9(2) . . . . ?
C3 C4 C5 C6 0.6(4) . . . . ?
C3 C8 C7 C6 1.1(4) . . . . ?
C28 C29 C30 C31 -0.3(4) . . . . ?
C28 C33 C32 C31 0.6(4) . . . . ?
C2 N1 N11 C12 -128.1(2) . . . . ?
C2 N1 C10 C9 59.0(3) . . . . ?
C2 C3 C4 C5 -176.1(2) . . . . ?
C2 C3 C8 C9 -3.2(4) . . . . ?
C2 C3 C8 C7 175.2(2) . . . . ?
C12 C28 C29 C30 178.3(2) . . . . ?
C12 C28 C33 C32 -178.3(2) . . . . ?
C15 O16 C17 C18 -105.4(3) . . . . ?
C29 C28 C12 O13 -22.3(4) . . . . ?
C29 C28 C12 N11 159.2(2) . . . . ?
C29 C28 C33 C32 -1.3(4) . . . . ?
C14 N20 C21 C22 -5.4(4) . . . . ?
C14 N20 C21 C26 177.1(2) . . . . ?
C33 C28 C12 O13 154.8(2) . . . . ?
C33 C28 C12 N11 -23.8(3) . . . . ?
C33 C28 C29 C30 1.1(4) . . . . ?
C21 N20 C14 C2 164.8(2) . . . . ?
C21 N20 C14 C15 -71.2(3) . . . . ?
C21 C22 C23 C24 0.5(4) . . . . ?
C9 C8 C7 C6 179.4(3) . . . . ?
C4 C3 C2 N1 174.3(2) . . . . ?
C4 C3 C2 C14 -64.4(3) . . . . ?
C4 C3 C8 C9 -179.7(2) . . . . ?
C4 C3 C8 C7 -1.4(4) . . . . ?
C4 C5 C6 C7 -0.9(4) . . . . ?
C8 C3 C2 N1 -2.3(3) . . . . ?
C8 C3 C2 C14 119.0(2) . . . . ?
C8 C3 C4 C5 0.6(4) . . . . ?
C8 C9 C10 N1 -60.2(3) . . . . ?
C8 C7 C6 C5 0.1(4) . . . . ?
C32 C31 C30 C29 -0.3(4) . . . . ?
C22 C21 C26 Br27 -179.87(18) . . . . ?
C22 C21 C26 C25 0.7(4) . . . . ?
C22 C23 C24 C25 0.0(4) . . . . ?
C30 C31 C32 C33 0.2(4) . . . . ?
C10 N1 N11 C12 99.0(2) . . . . ?
C10 N1 C2 C3 -27.1(3) . . . . ?
C10 N1 C2 C14 -150.7(2) . . . . ?
C10 C9 C8 C3 34.7(3) . . . . ?
C10 C9 C8 C7 -143.6(2) . . . . ?
C26 C25 C24 C23 -0.2(4) . . . . ?
C26 C21 C22 C23 -0.8(4) . . . . ?
C24 C25 C26 Br27 -179.6(2) . . . . ?
C24 C25 C26 C21 -0.2(4) . . . . ?
C17 O16 C15 O19 2.6(4) . . . . ?
C17 O16 C15 C14 -177.4(2) . . . . ?

_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 2.094
_oxdiff_exptl_absorpt_empirical_full_min 0.453
