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

data_2
_database_code_depnum_ccdc_archive 'CCDC 2089540'
loop_
_audit_author_name
_audit_author_address
'wang wenyao'
;Dalian University of Technology
China
;
_audit_update_record             
;
2021-06-12 deposited with the CCDC.	2021-07-13 downloaded from the CCDC.
;
_audit_creation_date             2021-06-11
_audit_creation_method           
;
Olex2 1.3-beta
(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         'C40 H33 Br N4 O'
_chemical_formula_sum            'C40 H33 Br N4 O'
_chemical_formula_weight         665.61
_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                   12.2987(7)
_cell_length_b                   12.4224(7)
_cell_length_c                   13.2018(8)
_cell_angle_alpha                75.801(2)
_cell_angle_beta                 69.663(2)
_cell_angle_gamma                66.4250(10)
_cell_volume                     1720.08(18)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9966
_cell_measurement_temperature    296.0
_cell_measurement_theta_max      25.462
_cell_measurement_theta_min      2.168
_shelx_estimated_absorpt_T_max   0.952
_shelx_estimated_absorpt_T_min   0.908
_exptl_absorpt_coefficient_mu    1.232
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5766
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1135 before and 0.0519 after correction.
The Ratio of minimum to maximum transmission is 0.7733.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'light colourless'
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.285
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             688
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.04
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0403
_diffrn_reflns_av_unetI/netI     0.0390
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            32619
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.550
_diffrn_reflns_theta_min         1.802
_diffrn_ambient_temperature      296.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.993
_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                   ?
_diffrn_source_current           50.0
_diffrn_source_power             2.5
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5061
_reflns_number_total             7890
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _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 V8.40A (Bruker, 2019)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.3-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.755
_refine_diff_density_min         -0.627
_refine_diff_density_rms         0.050
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     421
_refine_ls_number_reflns         7890
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0850
_refine_ls_R_factor_gt           0.0494
_refine_ls_restrained_S_all      1.029
_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)+(0.0806P)²+0.5388P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1373
_refine_ls_wR_factor_ref         0.1582
_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.a Ternary CH refined with riding coordinates:
 C16(H16), C23(H23), C24(H24)
2.b Aromatic/amide H refined with riding coordinates:
 C40(H40), C38(H38), C37(H37), C17(H17), C15(H15), C19(H19), C11(H11),
 C20(H20), C26(H26), C14(H14), C3(H3A), C30(H30), C22(H22), C13(H13), C21(H21),
 C12(H12), C27(H27), C2(H2), C28(H28), C5(H5), C1(H1), C29(H29), C6(H6)
2.c Idealised Me refined as rotating group:
 C34(H34A,H34B,H34C), C33(H33A,H33B,H33C)
;
_atom_sites_solution_hydrogens   mixed
_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 -0.09905(3) -0.11528(3) 0.94540(3) 0.08048(16) Uani 1 1 d . . . . .
O1 O 0.56047(17) 0.28325(17) 0.38919(18) 0.0661(5) Uani 1 1 d . . . . .
N4 N 0.11608(18) 0.26495(17) 0.70125(17) 0.0471(5) Uani 1 1 d . . . . .
N3 N 0.4095(2) 0.40264(19) 0.58475(19) 0.0499(5) Uani 1 1 d . . . . .
N2 N 0.3703(2) 0.57275(18) 0.33724(19) 0.0511(5) Uani 1 1 d . . . . .
N1 N 0.4670(2) 0.46713(18) 0.30418(18) 0.0510(5) Uani 1 1 d . . . . .
C31 C 0.2286(2) 0.2012(2) 0.65828(19) 0.0411(5) Uani 1 1 d . . . . .
C16 C 0.2750(2) 0.3654(2) 0.5137(2) 0.0407(5) Uani 1 1 d . . . . .
H16 H 0.196984 0.417491 0.556058 0.049 Uiso 1 1 calc R U . . .
C35 C 0.1287(2) 0.0683(2) 0.7507(2) 0.0459(6) Uani 1 1 d . . . . .
C8 C 0.3722(2) 0.4274(2) 0.4863(2) 0.0441(5) Uani 1 1 d . . . . .
C36 C 0.0517(2) 0.1861(2) 0.7589(2) 0.0461(6) Uani 1 1 d . . . . .
C23 C 0.3225(2) 0.2574(2) 0.59333(19) 0.0412(5) Uani 1 1 d . . . . .
H23 H 0.396372 0.198769 0.553363 0.049 Uiso 1 1 calc R U . . .
C7 C 0.4798(2) 0.3801(2) 0.3887(2) 0.0491(6) Uani 1 1 d . . . . .
C40 C 0.0846(2) -0.0223(2) 0.8049(2) 0.0538(6) Uani 1 1 d . . . . .
H40 H 0.135310 -0.101111 0.800401 0.065 Uiso 1 1 calc R U . . .
C9 C 0.3201(2) 0.5542(2) 0.4392(2) 0.0424(5) Uani 1 1 d . . . . .
C10 C 0.2175(2) 0.6492(2) 0.4974(2) 0.0468(6) Uani 1 1 d . . . . .
C18 C 0.2490(2) 0.3466(2) 0.4178(2) 0.0442(5) Uani 1 1 d . . . . .
C32 C 0.2542(2) 0.0678(2) 0.6799(2) 0.0463(6) Uani 1 1 d . . . . .
C38 C -0.1152(3) 0.1242(3) 0.8730(2) 0.0627(8) Uani 1 1 d . . . . .
H38 H -0.197300 0.141411 0.914288 0.075 Uiso 1 1 calc R U . . .
C24 C 0.3592(2) 0.3144(2) 0.6627(2) 0.0468(6) Uani 1 1 d . . . . .
H24 H 0.283434 0.357317 0.714554 0.056 Uiso 1 1 calc R U . . .
C37 C -0.0709(3) 0.2150(3) 0.8186(2) 0.0599(7) Uani 1 1 d . . . . .
H37 H -0.122351 0.293699 0.822196 0.072 Uiso 1 1 calc R U . . .
C39 C -0.0380(3) 0.0082(3) 0.8663(2) 0.0559(7) Uani 1 1 d . . . . .
C34 C 0.2885(3) 0.0176(3) 0.5735(3) 0.0644(8) Uani 1 1 d . . . . .
H34A H 0.226402 0.062309 0.536309 0.097 Uiso 1 1 calc R U . . .
H34B H 0.293778 -0.063715 0.589470 0.097 Uiso 1 1 calc R U . . .
H34C H 0.366935 0.022716 0.528168 0.097 Uiso 1 1 calc R U . . .
C17 C 0.1476(2) 0.4285(3) 0.3843(2) 0.0558(7) Uani 1 1 d . . . . .
H17 H 0.097113 0.493508 0.421844 0.067 Uiso 1 1 calc R U . . .
C25 C 0.4464(3) 0.2303(2) 0.7258(2) 0.0571(7) Uani 1 1 d . . . . .
C15 C 0.1919(3) 0.6472(2) 0.6083(3) 0.0602(7) Uani 1 1 d . . . . .
H15 H 0.239082 0.584081 0.647506 0.072 Uiso 1 1 calc R U . . .
C33 C 0.3539(3) -0.0006(2) 0.7393(3) 0.0662(8) Uani 1 1 d . . . . .
H33A H 0.430982 0.008275 0.694668 0.099 Uiso 1 1 calc R U . . .
H33B H 0.363134 -0.082945 0.753479 0.099 Uiso 1 1 calc R U . . .
H33C H 0.330033 0.029943 0.806856 0.099 Uiso 1 1 calc R U . . .
C19 C 0.3236(3) 0.2521(2) 0.3586(2) 0.0584(7) Uani 1 1 d . . . . .
H19 H 0.392629 0.197083 0.378945 0.070 Uiso 1 1 calc R U . . .
C4 C 0.5434(3) 0.4698(3) 0.1959(2) 0.0617(7) Uani 1 1 d . . . . .
C11 C 0.1457(3) 0.7437(3) 0.4410(3) 0.0690(8) Uani 1 1 d . . . . .
H11 H 0.161656 0.746702 0.366371 0.083 Uiso 1 1 calc R U . . .
C20 C 0.2974(4) 0.2381(3) 0.2703(3) 0.0731(9) Uani 1 1 d . . . . .
H20 H 0.348240 0.174327 0.231203 0.088 Uiso 1 1 calc R U . . .
C26 C 0.5667(3) 0.1670(3) 0.6743(3) 0.0753(9) Uani 1 1 d . . . . .
H26 H 0.595366 0.176763 0.598732 0.090 Uiso 1 1 calc R U . . .
C14 C 0.0957(3) 0.7394(3) 0.6612(3) 0.0779(10) Uani 1 1 d . . . . .
H14 H 0.079193 0.738093 0.735672 0.093 Uiso 1 1 calc R U . . .
C3 C 0.5158(4) 0.5688(3) 0.1231(3) 0.0788(10) Uani 1 1 d . . . . .
H3A H 0.446739 0.634744 0.144934 0.095 Uiso 1 1 calc R U . . .
C30 C 0.4066(4) 0.2134(3) 0.8382(3) 0.0804(10) Uani 1 1 d . . . . .
H30 H 0.325979 0.255932 0.874249 0.096 Uiso 1 1 calc R U . . .
C22 C 0.1208(3) 0.4147(4) 0.2964(3) 0.0756(9) Uani 1 1 d . . . . .
H22 H 0.052402 0.469993 0.275173 0.091 Uiso 1 1 calc R U . . .
C13 C 0.0264(3) 0.8305(3) 0.6053(4) 0.0857(11) Uani 1 1 d . . . . .
H13 H -0.037864 0.891649 0.641445 0.103 Uiso 1 1 calc R U . . .
C21 C 0.1944(4) 0.3202(4) 0.2405(3) 0.0812(10) Uani 1 1 d . . . . .
H21 H 0.175255 0.310773 0.181719 0.097 Uiso 1 1 calc R U . . .
C12 C 0.0498(3) 0.8339(3) 0.4961(4) 0.0882(11) Uani 1 1 d . . . . .
H12 H 0.001105 0.897191 0.458252 0.106 Uiso 1 1 calc R U . . .
C27 C 0.6451(4) 0.0887(3) 0.7353(6) 0.1113(18) Uani 1 1 d . . . . .
H27 H 0.726731 0.047576 0.700427 0.134 Uiso 1 1 calc R U . . .
C2 C 0.5903(5) 0.5711(4) 0.0172(3) 0.1017(14) Uani 1 1 d . . . . .
H2 H 0.571035 0.638748 -0.032131 0.122 Uiso 1 1 calc R U . . .
C28 C 0.6034(7) 0.0720(4) 0.8451(7) 0.131(2) Uani 1 1 d . . . . .
H28 H 0.655652 0.017790 0.885363 0.157 Uiso 1 1 calc R U . . .
C5 C 0.6467(4) 0.3721(4) 0.1640(3) 0.0958(13) Uani 1 1 d . . . . .
H5 H 0.666126 0.304339 0.213127 0.115 Uiso 1 1 calc R U . . .
C1 C 0.6913(5) 0.4757(4) -0.0154(4) 0.1157(17) Uani 1 1 d . . . . .
H1 H 0.740419 0.477192 -0.087169 0.139 Uiso 1 1 calc R U . . .
C29 C 0.4846(7) 0.1346(4) 0.8971(5) 0.122(2) Uani 1 1 d . . . . .
H29 H 0.456535 0.123601 0.972648 0.147 Uiso 1 1 calc R U . . .
C6 C 0.7207(5) 0.3769(5) 0.0576(4) 0.1222(18) Uani 1 1 d . . . . .
H6 H 0.791315 0.312249 0.035608 0.147 Uiso 1 1 calc R U . . .
H3 H 0.485(3) 0.381(3) 0.569(2) 0.053(8) Uiso 1 1 d . . . . .


_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 C39 1.897(3) . ?
O1 C7 1.216(3) . ?
N4 C31 1.289(3) . ?
N4 C36 1.415(3) . ?
N3 C8 1.449(3) . ?
N3 C24 1.479(3) . ?
N3 H3 0.82(3) . ?
N2 N1 1.414(3) . ?
N2 C9 1.277(3) . ?
N1 C7 1.354(3) . ?
N1 C4 1.412(4) . ?
C31 C23 1.490(3) . ?
C31 C32 1.530(3) . ?
C16 H16 0.9800 . ?
C16 C8 1.566(3) . ?
C16 C23 1.535(3) . ?
C16 C18 1.499(3) . ?
C35 C36 1.395(3) . ?
C35 C40 1.376(4) . ?
C35 C32 1.500(3) . ?
C8 C7 1.523(4) . ?
C8 C9 1.505(3) . ?
C36 C37 1.380(4) . ?
C23 H23 0.9800 . ?
C23 C24 1.551(3) . ?
C40 H40 0.9300 . ?
C40 C39 1.385(4) . ?
C9 C10 1.468(3) . ?
C10 C15 1.382(4) . ?
C10 C11 1.382(4) . ?
C18 C17 1.391(4) . ?
C18 C19 1.385(4) . ?
C32 C34 1.531(4) . ?
C32 C33 1.532(4) . ?
C38 H38 0.9300 . ?
C38 C37 1.381(4) . ?
C38 C39 1.377(4) . ?
C24 H24 0.9800 . ?
C24 C25 1.495(4) . ?
C37 H37 0.9300 . ?
C34 H34A 0.9600 . ?
C34 H34B 0.9600 . ?
C34 H34C 0.9600 . ?
C17 H17 0.9300 . ?
C17 C22 1.375(4) . ?
C25 C26 1.379(4) . ?
C25 C30 1.382(5) . ?
C15 H15 0.9300 . ?
C15 C14 1.391(4) . ?
C33 H33A 0.9600 . ?
C33 H33B 0.9600 . ?
C33 H33C 0.9600 . ?
C19 H19 0.9300 . ?
C19 C20 1.379(4) . ?
C4 C3 1.365(5) . ?
C4 C5 1.382(5) . ?
C11 H11 0.9300 . ?
C11 C12 1.387(5) . ?
C20 H20 0.9300 . ?
C20 C21 1.384(5) . ?
C26 H26 0.9300 . ?
C26 C27 1.389(5) . ?
C14 H14 0.9300 . ?
C14 C13 1.344(5) . ?
C3 H3A 0.9300 . ?
C3 C2 1.381(5) . ?
C30 H30 0.9300 . ?
C30 C29 1.370(6) . ?
C22 H22 0.9300 . ?
C22 C21 1.361(5) . ?
C13 H13 0.9300 . ?
C13 C12 1.361(6) . ?
C21 H21 0.9300 . ?
C12 H12 0.9300 . ?
C27 H27 0.9300 . ?
C27 C28 1.352(8) . ?
C2 H2 0.9300 . ?
C2 C1 1.355(6) . ?
C28 H28 0.9300 . ?
C28 C29 1.366(9) . ?
C5 H5 0.9300 . ?
C5 C6 1.385(5) . ?
C1 H1 0.9300 . ?
C1 C6 1.369(7) . ?
C29 H29 0.9300 . ?
C6 H6 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
C31 N4 C36 106.94(19) . . ?
C8 N3 C24 109.8(2) . . ?
C8 N3 H3 110(2) . . ?
C24 N3 H3 113(2) . . ?
C9 N2 N1 108.2(2) . . ?
C7 N1 N2 112.0(2) . . ?
C7 N1 C4 129.4(2) . . ?
C4 N1 N2 118.2(2) . . ?
N4 C31 C23 120.7(2) . . ?
N4 C31 C32 114.6(2) . . ?
C23 C31 C32 124.69(19) . . ?
C8 C16 H16 106.5 . . ?
C23 C16 H16 106.5 . . ?
C23 C16 C8 101.95(18) . . ?
C18 C16 H16 106.5 . . ?
C18 C16 C8 115.7(2) . . ?
C18 C16 C23 118.68(19) . . ?
C36 C35 C32 107.7(2) . . ?
C40 C35 C36 120.5(2) . . ?
C40 C35 C32 131.8(2) . . ?
N3 C8 C16 105.1(2) . . ?
N3 C8 C7 112.8(2) . . ?
N3 C8 C9 119.0(2) . . ?
C7 C8 C16 110.31(19) . . ?
C9 C8 C16 109.68(19) . . ?
C9 C8 C7 100.0(2) . . ?
C35 C36 N4 111.6(2) . . ?
C37 C36 N4 127.2(2) . . ?
C37 C36 C35 121.2(2) . . ?
C31 C23 C16 113.48(19) . . ?
C31 C23 H23 109.7 . . ?
C31 C23 C24 113.6(2) . . ?
C16 C23 H23 109.7 . . ?
C16 C23 C24 100.41(18) . . ?
C24 C23 H23 109.7 . . ?
O1 C7 N1 128.0(3) . . ?
O1 C7 C8 125.7(3) . . ?
N1 C7 C8 106.3(2) . . ?
C35 C40 H40 121.2 . . ?
C35 C40 C39 117.5(2) . . ?
C39 C40 H40 121.2 . . ?
N2 C9 C8 112.8(2) . . ?
N2 C9 C10 120.7(2) . . ?
C10 C9 C8 126.4(2) . . ?
C15 C10 C9 121.1(2) . . ?
C11 C10 C9 120.0(3) . . ?
C11 C10 C15 118.9(2) . . ?
C17 C18 C16 119.1(2) . . ?
C19 C18 C16 122.9(2) . . ?
C19 C18 C17 118.0(2) . . ?
C31 C32 C34 110.6(2) . . ?
C31 C32 C33 113.3(2) . . ?
C35 C32 C31 99.12(18) . . ?
C35 C32 C34 111.4(2) . . ?
C35 C32 C33 111.8(2) . . ?
C34 C32 C33 110.3(2) . . ?
C37 C38 H38 119.9 . . ?
C39 C38 H38 119.9 . . ?
C39 C38 C37 120.1(3) . . ?
N3 C24 C23 104.9(2) . . ?
N3 C24 H24 107.8 . . ?
N3 C24 C25 112.5(2) . . ?
C23 C24 H24 107.8 . . ?
C25 C24 C23 115.7(2) . . ?
C25 C24 H24 107.8 . . ?
C36 C37 C38 118.3(3) . . ?
C36 C37 H37 120.9 . . ?
C38 C37 H37 120.9 . . ?
C40 C39 Br1 118.2(2) . . ?
C38 C39 Br1 119.5(2) . . ?
C38 C39 C40 122.3(3) . . ?
C32 C34 H34A 109.5 . . ?
C32 C34 H34B 109.5 . . ?
C32 C34 H34C 109.5 . . ?
H34A C34 H34B 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?
C18 C17 H17 119.5 . . ?
C22 C17 C18 121.0(3) . . ?
C22 C17 H17 119.5 . . ?
C26 C25 C24 121.4(3) . . ?
C26 C25 C30 118.6(3) . . ?
C30 C25 C24 120.0(3) . . ?
C10 C15 H15 120.0 . . ?
C10 C15 C14 120.0(3) . . ?
C14 C15 H15 120.0 . . ?
C32 C33 H33A 109.5 . . ?
C32 C33 H33B 109.5 . . ?
C32 C33 H33C 109.5 . . ?
H33A C33 H33B 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 109.5 . . ?
C18 C19 H19 119.3 . . ?
C20 C19 C18 121.3(3) . . ?
C20 C19 H19 119.3 . . ?
C3 C4 N1 120.2(3) . . ?
C3 C4 C5 120.1(3) . . ?
C5 C4 N1 119.8(3) . . ?
C10 C11 H11 120.1 . . ?
C10 C11 C12 119.8(3) . . ?
C12 C11 H11 120.1 . . ?
C19 C20 H20 120.5 . . ?
C19 C20 C21 119.1(3) . . ?
C21 C20 H20 120.5 . . ?
C25 C26 H26 120.0 . . ?
C25 C26 C27 120.0(4) . . ?
C27 C26 H26 120.0 . . ?
C15 C14 H14 119.8 . . ?
C13 C14 C15 120.4(4) . . ?
C13 C14 H14 119.8 . . ?
C4 C3 H3A 119.9 . . ?
C4 C3 C2 120.1(3) . . ?
C2 C3 H3A 119.9 . . ?
C25 C30 H30 119.7 . . ?
C29 C30 C25 120.7(5) . . ?
C29 C30 H30 119.7 . . ?
C17 C22 H22 120.0 . . ?
C21 C22 C17 120.0(3) . . ?
C21 C22 H22 120.0 . . ?
C14 C13 H13 119.8 . . ?
C14 C13 C12 120.5(3) . . ?
C12 C13 H13 119.8 . . ?
C20 C21 H21 119.7 . . ?
C22 C21 C20 120.6(3) . . ?
C22 C21 H21 119.7 . . ?
C11 C12 H12 119.8 . . ?
C13 C12 C11 120.4(3) . . ?
C13 C12 H12 119.8 . . ?
C26 C27 H27 119.8 . . ?
C28 C27 C26 120.4(5) . . ?
C28 C27 H27 119.8 . . ?
C3 C2 H2 119.8 . . ?
C1 C2 C3 120.4(4) . . ?
C1 C2 H2 119.8 . . ?
C27 C28 H28 119.9 . . ?
C27 C28 C29 120.1(4) . . ?
C29 C28 H28 119.9 . . ?
C4 C5 H5 120.6 . . ?
C4 C5 C6 118.8(4) . . ?
C6 C5 H5 120.6 . . ?
C2 C1 H1 120.1 . . ?
C2 C1 C6 119.7(4) . . ?
C6 C1 H1 120.1 . . ?
C30 C29 H29 119.9 . . ?
C28 C29 C30 120.2(5) . . ?
C28 C29 H29 119.9 . . ?
C5 C6 H6 119.6 . . ?
C1 C6 C5 120.8(4) . . ?
C1 C6 H6 119.6 . . ?

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
N4 C31 C23 C16 -44.0(3) . . . . ?
N4 C31 C23 C24 69.9(3) . . . . ?
N4 C31 C32 C35 -2.1(3) . . . . ?
N4 C31 C32 C34 114.9(3) . . . . ?
N4 C31 C32 C33 -120.7(3) . . . . ?
N4 C36 C37 C38 -177.3(3) . . . . ?
N3 C8 C7 O1 43.6(3) . . . . ?
N3 C8 C7 N1 -135.8(2) . . . . ?
N3 C8 C9 N2 131.3(2) . . . . ?
N3 C8 C9 C10 -52.6(3) . . . . ?
N3 C24 C25 C26 -53.7(3) . . . . ?
N3 C24 C25 C30 127.2(3) . . . . ?
N2 N1 C7 O1 -172.8(3) . . . . ?
N2 N1 C7 C8 6.6(3) . . . . ?
N2 N1 C4 C3 -6.4(4) . . . . ?
N2 N1 C4 C5 173.0(3) . . . . ?
N2 C9 C10 C15 -156.2(3) . . . . ?
N2 C9 C10 C11 22.9(4) . . . . ?
N1 N2 C9 C8 -4.7(3) . . . . ?
N1 N2 C9 C10 178.9(2) . . . . ?
N1 C4 C3 C2 -179.8(3) . . . . ?
N1 C4 C5 C6 -179.5(4) . . . . ?
C31 N4 C36 C35 0.0(3) . . . . ?
C31 N4 C36 C37 179.1(3) . . . . ?
C31 C23 C24 N3 -158.0(2) . . . . ?
C31 C23 C24 C25 77.5(3) . . . . ?
C16 C8 C7 O1 -73.5(3) . . . . ?
C16 C8 C7 N1 107.1(2) . . . . ?
C16 C8 C9 N2 -107.8(2) . . . . ?
C16 C8 C9 C10 68.4(3) . . . . ?
C16 C23 C24 N3 -36.5(2) . . . . ?
C16 C23 C24 C25 -161.0(2) . . . . ?
C16 C18 C17 C22 179.7(3) . . . . ?
C16 C18 C19 C20 -179.5(3) . . . . ?
C35 C36 C37 C38 1.8(4) . . . . ?
C35 C40 C39 Br1 -178.0(2) . . . . ?
C35 C40 C39 C38 0.8(4) . . . . ?
C8 N3 C24 C23 17.0(3) . . . . ?
C8 N3 C24 C25 143.5(2) . . . . ?
C8 C16 C23 C31 162.85(19) . . . . ?
C8 C16 C23 C24 41.2(2) . . . . ?
C8 C16 C18 C17 -96.2(3) . . . . ?
C8 C16 C18 C19 82.2(3) . . . . ?
C8 C9 C10 C15 28.0(4) . . . . ?
C8 C9 C10 C11 -152.9(3) . . . . ?
C36 N4 C31 C23 -178.7(2) . . . . ?
C36 N4 C31 C32 1.4(3) . . . . ?
C36 C35 C40 C39 0.5(4) . . . . ?
C36 C35 C32 C31 1.9(3) . . . . ?
C36 C35 C32 C34 -114.5(2) . . . . ?
C36 C35 C32 C33 121.6(2) . . . . ?
C23 C31 C32 C35 178.0(2) . . . . ?
C23 C31 C32 C34 -65.0(3) . . . . ?
C23 C31 C32 C33 59.4(3) . . . . ?
C23 C16 C8 N3 -32.4(2) . . . . ?
C23 C16 C8 C7 89.4(2) . . . . ?
C23 C16 C8 C9 -161.4(2) . . . . ?
C23 C16 C18 C17 142.1(2) . . . . ?
C23 C16 C18 C19 -39.5(3) . . . . ?
C23 C24 C25 C26 66.8(3) . . . . ?
C23 C24 C25 C30 -112.2(3) . . . . ?
C7 N1 C4 C3 -178.0(3) . . . . ?
C7 N1 C4 C5 1.5(5) . . . . ?
C7 C8 C9 N2 8.2(3) . . . . ?
C7 C8 C9 C10 -175.7(2) . . . . ?
C40 C35 C36 N4 177.4(2) . . . . ?
C40 C35 C36 C37 -1.9(4) . . . . ?
C40 C35 C32 C31 -176.6(3) . . . . ?
C40 C35 C32 C34 67.0(4) . . . . ?
C40 C35 C32 C33 -56.9(4) . . . . ?
C9 N2 N1 C7 -1.4(3) . . . . ?
C9 N2 N1 C4 -174.3(2) . . . . ?
C9 C8 C7 O1 171.1(3) . . . . ?
C9 C8 C7 N1 -8.3(2) . . . . ?
C9 C10 C15 C14 178.7(3) . . . . ?
C9 C10 C11 C12 -179.2(3) . . . . ?
C10 C15 C14 C13 0.5(5) . . . . ?
C10 C11 C12 C13 0.5(6) . . . . ?
C18 C16 C8 N3 -162.7(2) . . . . ?
C18 C16 C8 C7 -40.9(3) . . . . ?
C18 C16 C8 C9 68.3(3) . . . . ?
C18 C16 C23 C31 -68.7(3) . . . . ?
C18 C16 C23 C24 169.7(2) . . . . ?
C18 C17 C22 C21 -0.3(5) . . . . ?
C18 C19 C20 C21 -0.1(5) . . . . ?
C32 C31 C23 C16 135.9(2) . . . . ?
C32 C31 C23 C24 -110.2(3) . . . . ?
C32 C35 C36 N4 -1.3(3) . . . . ?
C32 C35 C36 C37 179.5(2) . . . . ?
C32 C35 C40 C39 178.8(3) . . . . ?
C24 N3 C8 C16 9.5(3) . . . . ?
C24 N3 C8 C7 -110.7(2) . . . . ?
C24 N3 C8 C9 132.8(2) . . . . ?
C24 C25 C26 C27 -179.4(3) . . . . ?
C24 C25 C30 C29 178.5(3) . . . . ?
C37 C38 C39 Br1 177.9(2) . . . . ?
C37 C38 C39 C40 -0.8(5) . . . . ?
C39 C38 C37 C36 -0.5(5) . . . . ?
C17 C18 C19 C20 -1.0(4) . . . . ?
C17 C22 C21 C20 -0.8(6) . . . . ?
C25 C26 C27 C28 1.5(6) . . . . ?
C25 C30 C29 C28 0.4(6) . . . . ?
C15 C10 C11 C12 -0.2(5) . . . . ?
C15 C14 C13 C12 -0.2(6) . . . . ?
C19 C18 C17 C22 1.3(4) . . . . ?
C19 C20 C21 C22 1.0(5) . . . . ?
C4 N1 C7 O1 -0.9(5) . . . . ?
C4 N1 C7 C8 178.5(3) . . . . ?
C4 C3 C2 C1 -0.1(7) . . . . ?
C4 C5 C6 C1 -1.2(8) . . . . ?
C11 C10 C15 C14 -0.3(4) . . . . ?
C26 C25 C30 C29 -0.6(5) . . . . ?
C26 C27 C28 C29 -1.8(7) . . . . ?
C14 C13 C12 C11 -0.3(6) . . . . ?
C3 C4 C5 C6 -0.1(6) . . . . ?
C3 C2 C1 C6 -1.1(8) . . . . ?
C30 C25 C26 C27 -0.3(5) . . . . ?
C27 C28 C29 C30 0.9(7) . . . . ?
C2 C1 C6 C5 1.7(9) . . . . ?
C5 C4 C3 C2 0.7(6) . . . . ?

_smtbx_masks_special_details     ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 0.000 0.500 1.000 136.6 33.7 ?
2 0.405 0.819 0.936 23.1 0.0 ?
3 0.595 0.181 0.064 23.1 0.0 ?

_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_olex2_submission_special_instructions 'No special instructions were received'
