# Supplementary Information (SI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2025

####################################################################### 
# 
# 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_221014wqm
_database_code_depnum_ccdc_archive 'CCDC 2422261'
loop_
_audit_author_name
_audit_author_address
'Jie Yu'
;Anhui Agricultural University
China
;
_audit_update_record             
;
2025-02-07 deposited with the CCDC.	2025-04-03 downloaded from the CCDC.
;
_audit_creation_date             2022-10-14
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H14 Br Cl N2 O3'
_chemical_formula_sum            'C18 H14 Br Cl N2 O3'
_chemical_formula_weight         421.67
_chemical_absolute_configuration rmad
_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 0.0137 0.0067 '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 -0.9338 1.0006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3281 0.5435 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0241 0.0134 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0389 0.0241 '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           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   11.1043(3)
_cell_length_b                   13.4026(4)
_cell_length_c                   12.0631(4)
_cell_angle_alpha                90
_cell_angle_beta                 90.368(2)
_cell_angle_gamma                90
_cell_volume                     1795.27(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9812
_cell_measurement_temperature    213
_cell_measurement_theta_max      55.010
_cell_measurement_theta_min      2.869
_shelx_estimated_absorpt_T_max   0.861
_shelx_estimated_absorpt_T_min   0.813
_exptl_absorpt_coefficient_mu    3.083
_exptl_absorpt_correction_T_max  0.7508
_exptl_absorpt_correction_T_min  0.5988
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1013 before and 0.0726 after correction.
The Ratio of minimum to maximum transmission is 0.7975.
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    1.560
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             848
_exptl_crystal_size_max          0.07
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0458
_diffrn_reflns_av_unetI/netI     0.0408
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            24195
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         55.120
_diffrn_reflns_theta_min         3.463
_diffrn_ambient_temperature      213
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_source                   ?
_diffrn_source_current           2.86
_diffrn_source_power             0.1995708
_diffrn_source_voltage           69.78
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.897
_reflns_Friedel_fraction_full    0.986
_reflns_Friedel_fraction_max     0.977
_reflns_number_gt                6497
_reflns_number_total             6784
_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 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.287
_refine_diff_density_min         -0.356
_refine_diff_density_rms         0.050
_refine_ls_abs_structure_details 
;
 Flack x determined using 2908 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.041(7)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     453
_refine_ls_number_reflns         6784
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0274
_refine_ls_R_factor_gt           0.0258
_refine_ls_restrained_S_all      1.065
_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)+(0.0254P)²+0.2446P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0625
_refine_ls_wR_factor_ref         0.0638
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(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:
 C3(H3), C21(H21)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C5(H5), C6(H6), C8(H8), C9(H9), C11(H11), C15(H15), C16(H16),
 C17(H17), C18(H18), N3(H3A), C23(H23), C24(H24), C26(H26), C27(H27), C29(H29),
 C33(H33), C34(H34), C35(H35), C36(H36)
2.c Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C32(H32A,H32B,H32C)
;
_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 0.45759(4) 0.39454(3) 0.20073(3) 0.04555(12) Uani 1 1 d . . . . .
Cl1 Cl 1.14529(13) 0.32595(12) -0.04978(12) 0.0825(4) Uani 1 1 d . . . . .
O1 O 0.5440(2) 0.3931(2) 0.47451(18) 0.0382(5) Uani 1 1 d . . . . .
O2 O 0.7870(3) 0.3680(3) 0.7782(2) 0.0599(8) Uani 1 1 d . . . . .
O3 O 0.5881(3) 0.3740(3) 0.8113(2) 0.0543(8) Uani 1 1 d . . . . .
N1 N 0.8351(3) 0.3778(3) 0.3406(2) 0.0494(9) Uani 1 1 d . . . . .
H1 H 0.870864 0.375000 0.404865 0.059 Uiso 1 1 calc R U . . .
N2 N 0.7300(3) 0.3782(2) 0.5429(2) 0.0363(7) Uani 1 1 d . . . . .
C1 C 0.5647(3) 0.5040(3) 0.2224(3) 0.0329(7) Uani 1 1 d . . . . .
C2 C 0.6688(3) 0.4922(3) 0.2849(3) 0.0313(7) Uani 1 1 d . . . . .
C3 C 0.7060(3) 0.3927(3) 0.3375(3) 0.0350(7) Uani 1 1 d . . . . .
H3 H 0.668389 0.337457 0.295153 0.042 Uiso 1 1 calc R U . . .
C4 C 0.9045(3) 0.3678(2) 0.2463(3) 0.0339(8) Uani 1 1 d . . . . .
C5 C 1.0292(3) 0.3593(3) 0.2603(3) 0.0371(8) Uani 1 1 d . . . . .
H5 H 1.063247 0.362620 0.331699 0.044 Uiso 1 1 calc R U . . .
C6 C 1.1021(4) 0.3461(3) 0.1698(4) 0.0460(9) Uani 1 1 d . . . . .
H6 H 1.185815 0.339367 0.179396 0.055 Uiso 1 1 calc R U . . .
C7 C 1.0520(4) 0.3427(3) 0.0642(3) 0.0467(9) Uani 1 1 d . . . . .
C8 C 0.9303(4) 0.3526(3) 0.0491(3) 0.0487(10) Uani 1 1 d . . . . .
H8 H 0.897047 0.350574 -0.022775 0.058 Uiso 1 1 calc R U . . .
C9 C 0.8559(4) 0.3657(3) 0.1405(3) 0.0468(10) Uani 1 1 d . . . . .
H9 H 0.772392 0.373112 0.130169 0.056 Uiso 1 1 calc R U . . .
C10 C 0.6649(3) 0.3874(3) 0.4558(3) 0.0329(7) Uani 1 1 d . . . . .
C11 C 0.5357(3) 0.3874(3) 0.5877(3) 0.0391(8) Uani 1 1 d . . . . .
H11 H 0.464175 0.389531 0.628850 0.047 Uiso 1 1 calc R U . . .
C12 C 0.6467(3) 0.3783(3) 0.6292(3) 0.0339(7) Uani 1 1 d . . . . .
C13 C 0.6846(3) 0.3721(3) 0.7465(3) 0.0411(9) Uani 1 1 d . . . . .
C14 C 0.6119(5) 0.3715(5) 0.9295(3) 0.0754(16) Uani 1 1 d . . . . .
H14A H 0.649064 0.308302 0.948957 0.113 Uiso 1 1 calc R U . . .
H14B H 0.536765 0.378684 0.969308 0.113 Uiso 1 1 calc R U . . .
H14C H 0.665699 0.425682 0.949338 0.113 Uiso 1 1 calc R U . . .
C15 C 0.7429(3) 0.5753(3) 0.2969(3) 0.0400(8) Uani 1 1 d . . . . .
H15 H 0.813858 0.570197 0.339524 0.048 Uiso 1 1 calc R U . . .
C16 C 0.7142(4) 0.6645(3) 0.2477(4) 0.0495(10) Uani 1 1 d . . . . .
H16 H 0.765773 0.719557 0.256461 0.059 Uiso 1 1 calc R U . . .
C17 C 0.6101(4) 0.6740(3) 0.1853(4) 0.0520(10) Uani 1 1 d . . . . .
H17 H 0.591180 0.735350 0.151683 0.062 Uiso 1 1 calc R U . . .
C18 C 0.5341(4) 0.5938(3) 0.1725(3) 0.0454(9) Uani 1 1 d . . . . .
H18 H 0.462752 0.599639 0.130643 0.054 Uiso 1 1 calc R U . . .
Br2 Br -0.03402(3) 0.63162(3) 0.57236(3) 0.04370(11) Uani 1 1 d . . . . .
Cl2 Cl 0.64555(11) 0.64209(10) 0.83882(11) 0.0704(3) Uani 1 1 d . . . . .
O4 O 0.0501(2) 0.6202(2) 0.29874(19) 0.0433(6) Uani 1 1 d . . . . .
O5 O 0.0821(3) 0.5923(2) -0.0348(2) 0.0574(8) Uani 1 1 d . . . . .
O6 O 0.2812(3) 0.6169(3) -0.0118(2) 0.0688(10) Uani 1 1 d . . . . .
N3 N 0.3424(2) 0.6284(3) 0.4350(2) 0.0374(6) Uani 1 1 d . . . . .
H3A H 0.379403 0.631788 0.371715 0.045 Uiso 1 1 calc R U . . .
N4 N 0.2346(3) 0.6164(2) 0.2285(2) 0.0366(7) Uani 1 1 d . . . . .
C19 C 0.0643(3) 0.5169(2) 0.5509(3) 0.0307(7) Uani 1 1 d . . . . .
C20 C 0.1691(3) 0.5226(2) 0.4903(3) 0.0271(7) Uani 1 1 d . . . . .
C21 C 0.2131(3) 0.6184(2) 0.4348(3) 0.0291(7) Uani 1 1 d . . . . .
H21 H 0.178123 0.676327 0.474112 0.035 Uiso 1 1 calc R U . . .
C22 C 0.4097(3) 0.6327(3) 0.5308(3) 0.0325(7) Uani 1 1 d . . . . .
C23 C 0.3590(3) 0.6338(3) 0.6363(3) 0.0379(7) Uani 1 1 d . . . . .
H23 H 0.274745 0.632920 0.643752 0.046 Uiso 1 1 calc R U . . .
C24 C 0.4315(4) 0.6360(3) 0.7306(3) 0.0437(8) Uani 1 1 d . . . . .
H24 H 0.396554 0.635567 0.801386 0.052 Uiso 1 1 calc R U . . .
C25 C 0.5547(3) 0.6388(3) 0.7200(3) 0.0437(9) Uani 1 1 d . . . . .
C26 C 0.6074(3) 0.6389(3) 0.6172(4) 0.0469(9) Uani 1 1 d . . . . .
H26 H 0.691719 0.640564 0.610921 0.056 Uiso 1 1 calc R U . . .
C27 C 0.5355(3) 0.6366(3) 0.5227(3) 0.0385(8) Uani 1 1 d . . . . .
H27 H 0.571596 0.637565 0.452408 0.046 Uiso 1 1 calc R U . . .
C28 C 0.1713(3) 0.6205(3) 0.3164(3) 0.0316(7) Uani 1 1 d . . . . .
C29 C 0.0389(3) 0.6162(3) 0.1857(3) 0.0446(9) Uani 1 1 d . . . . .
H29 H -0.033810 0.615492 0.145394 0.054 Uiso 1 1 calc R U . . .
C30 C 0.1491(3) 0.6135(3) 0.1428(3) 0.0366(8) Uani 1 1 d . . . . .
C31 C 0.1820(4) 0.6081(3) 0.0251(3) 0.0451(10) Uani 1 1 d . . . . .
C32 C 0.0956(6) 0.5866(5) -0.1540(4) 0.0778(16) Uani 1 1 d . . . . .
H32A H 0.017797 0.574096 -0.188150 0.117 Uiso 1 1 calc R U . . .
H32B H 0.150376 0.532678 -0.172155 0.117 Uiso 1 1 calc R U . . .
H32C H 0.127844 0.649094 -0.181360 0.117 Uiso 1 1 calc R U . . .
C33 C 0.2365(3) 0.4358(3) 0.4802(3) 0.0336(7) Uani 1 1 d . . . . .
H33 H 0.307548 0.436846 0.438310 0.040 Uiso 1 1 calc R U . . .
C34 C 0.2014(4) 0.3484(3) 0.5301(3) 0.0424(9) Uani 1 1 d . . . . .
H34 H 0.249017 0.290801 0.522902 0.051 Uiso 1 1 calc R U . . .
C35 C 0.0960(4) 0.3449(3) 0.5908(3) 0.0417(9) Uani 1 1 d . . . . .
H35 H 0.072138 0.284904 0.624621 0.050 Uiso 1 1 calc R U . . .
C36 C 0.0264(3) 0.4289(3) 0.6018(3) 0.0375(8) Uani 1 1 d . . . . .
H36 H -0.045323 0.427254 0.642705 0.045 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C1 1.906(3) . ?
Cl1 C7 1.742(4) . ?
O1 C10 1.365(4) . ?
O1 C11 1.371(4) . ?
O2 C13 1.199(5) . ?
O3 C13 1.331(5) . ?
O3 C14 1.448(5) . ?
N1 H1 0.8700 . ?
N1 C3 1.447(4) . ?
N1 C4 1.384(4) . ?
N2 C10 1.278(4) . ?
N2 C12 1.397(4) . ?
C1 C2 1.384(5) . ?
C1 C18 1.387(5) . ?
C2 C3 1.533(5) . ?
C2 C15 1.392(5) . ?
C3 H3 0.9900 . ?
C3 C10 1.503(5) . ?
C4 C5 1.399(5) . ?
C4 C9 1.384(5) . ?
C5 H5 0.9400 . ?
C5 C6 1.375(5) . ?
C6 H6 0.9400 . ?
C6 C7 1.387(6) . ?
C7 C8 1.369(6) . ?
C8 H8 0.9400 . ?
C8 C9 1.393(5) . ?
C9 H9 0.9400 . ?
C11 H11 0.9400 . ?
C11 C12 1.333(5) . ?
C12 C13 1.476(5) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 H14C 0.9700 . ?
C15 H15 0.9400 . ?
C15 C16 1.371(6) . ?
C16 H16 0.9400 . ?
C16 C17 1.381(6) . ?
C17 H17 0.9400 . ?
C17 C18 1.375(6) . ?
C18 H18 0.9400 . ?
Br2 C19 1.905(3) . ?
Cl2 C25 1.748(4) . ?
O4 C28 1.361(4) . ?
O4 C29 1.370(4) . ?
O5 C31 1.337(5) . ?
O5 C32 1.448(5) . ?
O6 C31 1.197(5) . ?
N3 H3A 0.8700 . ?
N3 C21 1.442(4) . ?
N3 C22 1.373(4) . ?
N4 C28 1.278(4) . ?
N4 C30 1.399(4) . ?
C19 C20 1.380(5) . ?
C19 C36 1.395(5) . ?
C20 C21 1.530(4) . ?
C20 C33 1.389(5) . ?
C21 H21 0.9900 . ?
C21 C28 1.499(4) . ?
C22 C23 1.396(5) . ?
C22 C27 1.403(5) . ?
C23 H23 0.9400 . ?
C23 C24 1.390(5) . ?
C24 H24 0.9400 . ?
C24 C25 1.375(5) . ?
C25 C26 1.375(6) . ?
C26 H26 0.9400 . ?
C26 C27 1.388(5) . ?
C27 H27 0.9400 . ?
C29 H29 0.9400 . ?
C29 C30 1.331(5) . ?
C30 C31 1.470(5) . ?
C32 H32A 0.9700 . ?
C32 H32B 0.9700 . ?
C32 H32C 0.9700 . ?
C33 H33 0.9400 . ?
C33 C34 1.374(5) . ?
C34 H34 0.9400 . ?
C34 C35 1.386(6) . ?
C35 H35 0.9400 . ?
C35 C36 1.373(5) . ?
C36 H36 0.9400 . ?

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
C10 O1 C11 103.5(3) . . ?
C13 O3 C14 115.9(3) . . ?
C3 N1 H1 118.4 . . ?
C4 N1 H1 118.4 . . ?
C4 N1 C3 123.3(3) . . ?
C10 N2 C12 103.8(3) . . ?
C2 C1 Br1 120.3(3) . . ?
C2 C1 C18 122.5(3) . . ?
C18 C1 Br1 117.2(3) . . ?
C1 C2 C3 123.1(3) . . ?
C1 C2 C15 117.2(3) . . ?
C15 C2 C3 119.7(3) . . ?
N1 C3 C2 113.3(3) . . ?
N1 C3 H3 109.0 . . ?
N1 C3 C10 106.0(3) . . ?
C2 C3 H3 109.0 . . ?
C10 C3 C2 110.6(3) . . ?
C10 C3 H3 109.0 . . ?
N1 C4 C5 117.7(3) . . ?
C9 C4 N1 123.0(3) . . ?
C9 C4 C5 119.3(3) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 C4 120.2(3) . . ?
C6 C5 H5 119.9 . . ?
C5 C6 H6 120.1 . . ?
C5 C6 C7 119.9(4) . . ?
C7 C6 H6 120.1 . . ?
C6 C7 Cl1 119.5(3) . . ?
C8 C7 Cl1 119.9(3) . . ?
C8 C7 C6 120.6(4) . . ?
C7 C8 H8 120.1 . . ?
C7 C8 C9 119.7(4) . . ?
C9 C8 H8 120.1 . . ?
C4 C9 C8 120.2(4) . . ?
C4 C9 H9 119.9 . . ?
C8 C9 H9 119.9 . . ?
O1 C10 C3 117.3(3) . . ?
N2 C10 O1 114.9(3) . . ?
N2 C10 C3 127.7(3) . . ?
O1 C11 H11 125.9 . . ?
C12 C11 O1 108.1(3) . . ?
C12 C11 H11 125.9 . . ?
N2 C12 C13 121.9(3) . . ?
C11 C12 N2 109.6(3) . . ?
C11 C12 C13 128.5(3) . . ?
O2 C13 O3 125.4(4) . . ?
O2 C13 C12 124.9(3) . . ?
O3 C13 C12 109.7(3) . . ?
O3 C14 H14A 109.5 . . ?
O3 C14 H14B 109.5 . . ?
O3 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C2 C15 H15 119.5 . . ?
C16 C15 C2 121.1(4) . . ?
C16 C15 H15 119.5 . . ?
C15 C16 H16 119.7 . . ?
C15 C16 C17 120.6(4) . . ?
C17 C16 H16 119.7 . . ?
C16 C17 H17 120.0 . . ?
C18 C17 C16 120.0(4) . . ?
C18 C17 H17 120.0 . . ?
C1 C18 H18 120.6 . . ?
C17 C18 C1 118.7(4) . . ?
C17 C18 H18 120.6 . . ?
C28 O4 C29 103.9(3) . . ?
C31 O5 C32 117.0(4) . . ?
C21 N3 H3A 118.6 . . ?
C22 N3 H3A 118.6 . . ?
C22 N3 C21 122.7(3) . . ?
C28 N4 C30 103.9(3) . . ?
C20 C19 Br2 120.9(2) . . ?
C20 C19 C36 122.5(3) . . ?
C36 C19 Br2 116.6(3) . . ?
C19 C20 C21 123.4(3) . . ?
C19 C20 C33 117.2(3) . . ?
C33 C20 C21 119.4(3) . . ?
N3 C21 C20 113.5(3) . . ?
N3 C21 H21 108.7 . . ?
N3 C21 C28 107.6(3) . . ?
C20 C21 H21 108.7 . . ?
C28 C21 C20 109.5(3) . . ?
C28 C21 H21 108.7 . . ?
N3 C22 C23 123.2(3) . . ?
N3 C22 C27 118.7(3) . . ?
C23 C22 C27 118.1(3) . . ?
C22 C23 H23 119.6 . . ?
C24 C23 C22 120.8(3) . . ?
C24 C23 H23 119.6 . . ?
C23 C24 H24 120.1 . . ?
C25 C24 C23 119.7(4) . . ?
C25 C24 H24 120.1 . . ?
C24 C25 Cl2 119.5(3) . . ?
C26 C25 Cl2 119.5(3) . . ?
C26 C25 C24 120.9(3) . . ?
C25 C26 H26 120.2 . . ?
C25 C26 C27 119.7(3) . . ?
C27 C26 H26 120.2 . . ?
C22 C27 H27 119.6 . . ?
C26 C27 C22 120.8(3) . . ?
C26 C27 H27 119.6 . . ?
O4 C28 C21 116.7(3) . . ?
N4 C28 O4 114.7(3) . . ?
N4 C28 C21 128.4(3) . . ?
O4 C29 H29 126.0 . . ?
C30 C29 O4 108.1(3) . . ?
C30 C29 H29 126.0 . . ?
N4 C30 C31 122.9(3) . . ?
C29 C30 N4 109.5(3) . . ?
C29 C30 C31 127.6(4) . . ?
O5 C31 C30 108.7(4) . . ?
O6 C31 O5 125.2(4) . . ?
O6 C31 C30 126.1(4) . . ?
O5 C32 H32A 109.5 . . ?
O5 C32 H32B 109.5 . . ?
O5 C32 H32C 109.5 . . ?
H32A C32 H32B 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
C20 C33 H33 119.3 . . ?
C34 C33 C20 121.4(3) . . ?
C34 C33 H33 119.3 . . ?
C33 C34 H34 119.9 . . ?
C33 C34 C35 120.2(3) . . ?
C35 C34 H34 119.9 . . ?
C34 C35 H35 120.0 . . ?
C36 C35 C34 120.0(3) . . ?
C36 C35 H35 120.0 . . ?
C19 C36 H36 120.7 . . ?
C35 C36 C19 118.6(3) . . ?
C35 C36 H36 120.7 . . ?

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 C2 C3 1.4(4) . . . . ?
Br1 C1 C2 C15 179.8(3) . . . . ?
Br1 C1 C18 C17 -179.3(3) . . . . ?
Cl1 C7 C8 C9 179.8(3) . . . . ?
O1 C11 C12 N2 0.2(4) . . . . ?
O1 C11 C12 C13 178.2(3) . . . . ?
N1 C3 C10 O1 -176.0(3) . . . . ?
N1 C3 C10 N2 4.2(5) . . . . ?
N1 C4 C5 C6 178.0(4) . . . . ?
N1 C4 C9 C8 -178.1(4) . . . . ?
N2 C12 C13 O2 1.0(6) . . . . ?
N2 C12 C13 O3 179.7(3) . . . . ?
C1 C2 C3 N1 145.9(3) . . . . ?
C1 C2 C3 C10 -95.3(4) . . . . ?
C1 C2 C15 C16 -0.7(5) . . . . ?
C2 C1 C18 C17 0.1(6) . . . . ?
C2 C3 C10 O1 60.9(4) . . . . ?
C2 C3 C10 N2 -119.0(4) . . . . ?
C2 C15 C16 C17 0.4(6) . . . . ?
C3 N1 C4 C5 176.6(4) . . . . ?
C3 N1 C4 C9 -3.6(6) . . . . ?
C3 C2 C15 C16 177.7(3) . . . . ?
C4 N1 C3 C2 -65.2(5) . . . . ?
C4 N1 C3 C10 173.4(3) . . . . ?
C4 C5 C6 C7 1.0(6) . . . . ?
C5 C4 C9 C8 1.6(6) . . . . ?
C5 C6 C7 Cl1 180.0(3) . . . . ?
C5 C6 C7 C8 0.1(6) . . . . ?
C6 C7 C8 C9 -0.3(6) . . . . ?
C7 C8 C9 C4 -0.6(6) . . . . ?
C9 C4 C5 C6 -1.8(5) . . . . ?
C10 O1 C11 C12 -0.4(4) . . . . ?
C10 N2 C12 C11 0.1(4) . . . . ?
C10 N2 C12 C13 -178.1(3) . . . . ?
C11 O1 C10 N2 0.5(4) . . . . ?
C11 O1 C10 C3 -179.4(3) . . . . ?
C11 C12 C13 O2 -176.8(4) . . . . ?
C11 C12 C13 O3 1.9(6) . . . . ?
C12 N2 C10 O1 -0.4(4) . . . . ?
C12 N2 C10 C3 179.5(4) . . . . ?
C14 O3 C13 O2 0.4(6) . . . . ?
C14 O3 C13 C12 -178.2(4) . . . . ?
C15 C2 C3 N1 -32.5(4) . . . . ?
C15 C2 C3 C10 86.3(4) . . . . ?
C15 C16 C17 C18 0.2(7) . . . . ?
C16 C17 C18 C1 -0.5(6) . . . . ?
C18 C1 C2 C3 -178.0(3) . . . . ?
C18 C1 C2 C15 0.4(5) . . . . ?
Br2 C19 C20 C21 -1.1(4) . . . . ?
Br2 C19 C20 C33 179.0(2) . . . . ?
Br2 C19 C36 C35 -178.4(3) . . . . ?
Cl2 C25 C26 C27 -179.8(3) . . . . ?
O4 C29 C30 N4 -0.4(5) . . . . ?
O4 C29 C30 C31 179.6(3) . . . . ?
N3 C21 C28 O4 -174.8(3) . . . . ?
N3 C21 C28 N4 10.0(5) . . . . ?
N3 C22 C23 C24 178.6(4) . . . . ?
N3 C22 C27 C26 -178.6(4) . . . . ?
N4 C30 C31 O5 171.4(3) . . . . ?
N4 C30 C31 O6 -8.9(6) . . . . ?
C19 C20 C21 N3 145.1(3) . . . . ?
C19 C20 C21 C28 -94.7(4) . . . . ?
C19 C20 C33 C34 -1.1(5) . . . . ?
C20 C19 C36 C35 -0.1(5) . . . . ?
C20 C21 C28 O4 61.4(4) . . . . ?
C20 C21 C28 N4 -113.8(4) . . . . ?
C20 C33 C34 C35 0.9(6) . . . . ?
C21 N3 C22 C23 -3.8(6) . . . . ?
C21 N3 C22 C27 176.3(3) . . . . ?
C21 C20 C33 C34 179.0(3) . . . . ?
C22 N3 C21 C20 -61.0(4) . . . . ?
C22 N3 C21 C28 177.7(3) . . . . ?
C22 C23 C24 C25 1.0(7) . . . . ?
C23 C22 C27 C26 1.5(6) . . . . ?
C23 C24 C25 Cl2 179.8(3) . . . . ?
C23 C24 C25 C26 -0.4(7) . . . . ?
C24 C25 C26 C27 0.3(7) . . . . ?
C25 C26 C27 C22 -0.9(6) . . . . ?
C27 C22 C23 C24 -1.6(6) . . . . ?
C28 O4 C29 C30 0.5(4) . . . . ?
C28 N4 C30 C29 0.1(4) . . . . ?
C28 N4 C30 C31 -179.9(3) . . . . ?
C29 O4 C28 N4 -0.6(4) . . . . ?
C29 O4 C28 C21 -176.4(3) . . . . ?
C29 C30 C31 O5 -8.6(5) . . . . ?
C29 C30 C31 O6 171.1(5) . . . . ?
C30 N4 C28 O4 0.3(4) . . . . ?
C30 N4 C28 C21 175.6(3) . . . . ?
C32 O5 C31 O6 -0.8(6) . . . . ?
C32 O5 C31 C30 178.9(4) . . . . ?
C33 C20 C21 N3 -35.0(4) . . . . ?
C33 C20 C21 C28 85.2(3) . . . . ?
C33 C34 C35 C36 -0.2(6) . . . . ?
C34 C35 C36 C19 -0.2(5) . . . . ?
C36 C19 C20 C21 -179.3(3) . . . . ?
C36 C19 C20 C33 0.8(5) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
