# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2024

####################################################################### 
# 
# 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_1900_2
_database_code_depnum_ccdc_archive 'CCDC 2308429'
loop_
_audit_author_name
_audit_author_address
'Zhi Zhou'
;Guangzhou Medical University
China
;
_audit_update_record             
;
2023-11-16 deposited with the CCDC.	2024-02-25 downloaded from the CCDC.
;
_audit_creation_date             2022-05-08
_audit_creation_method           
;
Olex2 1.5-beta
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H19 Br F2 N2 O'
_chemical_formula_sum            'C22 H19 Br F2 N2 O'
_chemical_formula_weight         445.30
_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'
F F 0.0727 0.0534 '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      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                   9.26640(10)
_cell_length_b                   11.0963(2)
_cell_length_c                   11.4001(2)
_cell_angle_alpha                65.9180(10)
_cell_angle_beta                 89.2430(10)
_cell_angle_gamma                69.2100(10)
_cell_volume                     988.52(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    7668
_cell_measurement_temperature    200.00(10)
_cell_measurement_theta_max      70.7970
_cell_measurement_theta_min      4.2960
_shelx_estimated_absorpt_T_max   0.788
_shelx_estimated_absorpt_T_min   0.687
_exptl_absorpt_coefficient_mu    3.123
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.69400
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.33c (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.496
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             452
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0143
_diffrn_reflns_av_unetI/netI     0.0141
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.969
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            9231
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.969
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.317
_diffrn_reflns_theta_min         4.299
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      200.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    107.00 132.00   0.50    0.50    --   42.30  77.00-180.00   50
  2  ω     93.00 130.00   0.50    0.50    --   42.30  77.00  90.00   74
  3  ω    102.00 132.00   0.50    0.50    --   42.30  77.00 -90.00   60
  4  ω    -35.00  73.00   0.50    0.50    --   42.30 -57.00 -30.00  216
  5  ω     14.00  51.00   0.50    0.50    --   42.30  57.00 150.00   74
  6  ω     98.00 131.00   0.50    0.50    --   42.30  57.00 150.00   66
  7  ω     86.00 132.00   0.50    0.50    --   42.30  77.00-120.00   92
  8  ω     42.00  78.00   0.50    0.50    --   42.30 -82.00-180.00   72
  9  ω    -38.00  66.00   0.50    0.50    --   42.30 -57.00-150.00  208
 10  ω    -24.00  28.00   0.50    0.50    --   42.30 -82.00-180.00  104
 11  ω     41.00  68.00   0.50    0.50    --  101.00 -82.00 -30.00   54
 12  ω     12.00 103.00   0.50    0.50    --  101.00 -82.00-180.00  182
 13  ω     76.00 112.00   0.50    0.50    --  101.00 -82.00 120.00   72
 14  ω     12.00 125.00   0.50    0.50    --  101.00 -63.00  30.00  226
 15  ω    116.00 175.00   0.50    0.50    --  101.00 -25.00 -60.00  118
 16  ω     14.00 144.00   0.50    0.50    --  101.00 -82.00  30.00  260
 17  ω     13.00  65.00   0.50    0.50    --  101.00 -25.00 -60.00  104
 18  ω     24.00 109.00   0.50    0.50    --  101.00 -82.00 -60.00  170
 19  ω     89.00 114.00   0.50    0.50    --  101.00 -82.00  90.00   50
 20  ω     69.00 104.00   0.50    0.50    --  101.00 -63.00-150.00   70
 21  ω     58.00  83.00   0.50    0.50    --  101.00 -82.00  90.00   50
 22  ω     98.00 184.00   0.50    0.50    --  101.00 -12.00  60.00  172
 23  ω     17.00  52.00   0.50    0.50    --  101.00 -63.00-150.00   70
 24  ω     19.00 138.00   0.50    0.50    --  101.00 -82.00-120.00  238
 25  ω     15.00  85.00   0.50    0.50    --  101.00 -12.00  60.00  140
 26  ω     32.00  58.00   0.50    0.50    --  101.00 -82.00 120.00   52
 27  ω    101.00 188.00   0.50    0.50    --  101.00 -12.00-180.00  174
 28  ω     94.00 119.00   0.50    0.50    --  101.00 -82.00 150.00   50
 29  ω     13.00  85.00   0.50    0.50    --  101.00 -12.00-180.00  144
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1779861000
_diffrn_orient_matrix_UB_12      0.0813772000
_diffrn_orient_matrix_UB_13      -0.0412258000
_diffrn_orient_matrix_UB_21      -0.0205707000
_diffrn_orient_matrix_UB_22      -0.1425951000
_diffrn_orient_matrix_UB_23      0.0394401000
_diffrn_orient_matrix_UB_31      -0.0170961000
_diffrn_orient_matrix_UB_32      -0.0120027000
_diffrn_orient_matrix_UB_33      0.1385221000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\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                3596
_reflns_number_total             3711
_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 1.171.39.33c (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2017/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         1.385
_refine_diff_density_min         -1.491
_refine_diff_density_rms         0.080
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     255
_refine_ls_number_reflns         3711
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0466
_refine_ls_R_factor_gt           0.0456
_refine_ls_restrained_S_all      1.046
_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)+(0.0466P)²+1.5162P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1118
_refine_ls_wR_factor_ref         0.1125
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C7(H7), C9(H9), C11(H11)
2.b Secondary CH2 refined with riding coordinates:
 C19(H19A,H19B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C13(H13), C14(H14), C16(H16), C17(H17)
2.d Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C), C22(H22A,H22B,H22C)
;
_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 0.82036(5) -0.15506(3) 0.47805(4) 0.07038(18) Uani 1 1 d . . . . .
F1 F 0.6351(2) 0.57645(18) 0.42092(15) 0.0424(4) Uani 1 1 d . . . . .
F2 F 0.77091(17) 0.46595(18) 0.31027(19) 0.0470(4) Uani 1 1 d . . . . .
O1 O 0.2666(2) 0.4079(2) 0.05322(19) 0.0369(4) Uani 1 1 d . . . . .
N1 N 0.2314(2) 0.6745(2) 0.15437(19) 0.0247(4) Uani 1 1 d . . . . .
N2 N 0.3147(2) 0.5415(2) 0.1450(2) 0.0259(4) Uani 1 1 d . . . . .
C1 C 0.3297(3) 0.8101(3) 0.2397(2) 0.0294(5) Uani 1 1 d . . . . .
C2 C 0.2165(3) 0.9139(3) 0.2652(3) 0.0402(6) Uani 1 1 d . . . . .
H2 H 0.130626 0.898210 0.301525 0.048 Uiso 1 1 calc R U . . .
C3 C 0.2343(4) 1.0426(3) 0.2351(3) 0.0507(8) Uani 1 1 d . . . . .
H3 H 0.157656 1.114564 0.248983 0.061 Uiso 1 1 calc R U . . .
C4 C 0.3637(4) 1.0645(3) 0.1852(3) 0.0508(8) Uani 1 1 d . . . . .
H4 H 0.373231 1.151143 0.165343 0.061 Uiso 1 1 calc R U . . .
C5 C 0.4801(4) 0.9584(3) 0.1644(3) 0.0435(7) Uani 1 1 d . . . . .
H5 H 0.568680 0.972260 0.132698 0.052 Uiso 1 1 calc R U . . .
C6 C 0.4620(3) 0.8313(3) 0.1915(2) 0.0315(5) Uani 1 1 d . . . . .
C7 C 0.5737(3) 0.7024(3) 0.1812(3) 0.0307(5) Uani 1 1 d . . . . .
H7 H 0.628678 0.712006 0.105821 0.037 Uiso 1 1 calc R U . . .
C8 C 0.4943(3) 0.5911(2) 0.2313(2) 0.0237(5) Uani 1 1 d . . . . .
C9 C 0.3335(3) 0.6657(2) 0.2594(2) 0.0239(5) Uani 1 1 d . . . . .
H9 H 0.314946 0.611092 0.346480 0.029 Uiso 1 1 calc R U . . .
C10 C 0.6360(3) 0.5708(3) 0.3045(3) 0.0315(5) Uani 1 1 d . . . . .
C11 C 0.4837(3) 0.4986(2) 0.1653(2) 0.0242(5) Uani 1 1 d . . . . .
H11 H 0.520941 0.528420 0.081187 0.029 Uiso 1 1 calc R U . . .
C12 C 0.5653(3) 0.3386(2) 0.2439(2) 0.0259(5) Uani 1 1 d . . . . .
C13 C 0.5309(3) 0.2682(3) 0.3655(3) 0.0329(5) Uani 1 1 d . . . . .
H13 H 0.455993 0.319996 0.400283 0.039 Uiso 1 1 calc R U . . .
C14 C 0.6061(3) 0.1218(3) 0.4362(3) 0.0389(6) Uani 1 1 d . . . . .
H14 H 0.582390 0.075152 0.517849 0.047 Uiso 1 1 calc R U . . .
C15 C 0.7169(3) 0.0465(3) 0.3832(3) 0.0404(6) Uani 1 1 d . . . . .
C16 C 0.7527(4) 0.1133(3) 0.2625(3) 0.0474(7) Uani 1 1 d . . . . .
H16 H 0.827295 0.060982 0.227913 0.057 Uiso 1 1 calc R U . . .
C17 C 0.6760(3) 0.2596(3) 0.1931(3) 0.0387(6) Uani 1 1 d . . . . .
H17 H 0.699231 0.305557 0.110976 0.046 Uiso 1 1 calc R U . . .
C18 C 0.0719(3) 0.6698(3) 0.1743(3) 0.0340(6) Uani 1 1 d . . . . .
C19 C 0.0570(3) 0.5972(3) 0.0877(3) 0.0395(6) Uani 1 1 d . . . . .
H19A H -0.007616 0.542130 0.121077 0.047 Uiso 1 1 calc R U . . .
H19B H 0.011123 0.667839 -0.000719 0.047 Uiso 1 1 calc R U . . .
C20 C 0.2220(3) 0.5009(3) 0.0923(2) 0.0291(5) Uani 1 1 d . . . . .
C21 C -0.0488(3) 0.8215(4) 0.1235(4) 0.0555(9) Uani 1 1 d . . . . .
H21A H -0.034533 0.864202 0.178380 0.083 Uiso 1 1 calc R U . . .
H21B H -0.151665 0.819902 0.123563 0.083 Uiso 1 1 calc R U . . .
H21C H -0.036384 0.876273 0.036474 0.083 Uiso 1 1 calc R U . . .
C22 C 0.0632(4) 0.5801(4) 0.3153(3) 0.0515(8) Uani 1 1 d . . . . .
H22A H 0.143586 0.486279 0.345384 0.077 Uiso 1 1 calc R U . . .
H22B H -0.037151 0.573001 0.320749 0.077 Uiso 1 1 calc R U . . .
H22C H 0.077684 0.624673 0.368336 0.077 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 C15 1.904(3) . ?
F1 C10 1.354(3) . ?
F2 C10 1.352(3) . ?
O1 C20 1.226(3) . ?
N1 N2 1.450(3) . ?
N1 C9 1.485(3) . ?
N1 C18 1.508(3) . ?
N2 C11 1.458(3) . ?
N2 C20 1.346(3) . ?
C1 C2 1.385(4) . ?
C1 C6 1.393(4) . ?
C1 C9 1.512(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.397(4) . ?
C3 H3 0.9300 . ?
C3 C4 1.377(5) . ?
C4 H4 0.9300 . ?
C4 C5 1.388(5) . ?
C5 H5 0.9300 . ?
C5 C6 1.386(4) . ?
C6 C7 1.489(4) . ?
C7 H7 0.9800 . ?
C7 C8 1.566(3) . ?
C7 C10 1.480(4) . ?
C8 C9 1.529(3) . ?
C8 C10 1.462(3) . ?
C8 C11 1.527(3) . ?
C9 H9 0.9800 . ?
C11 H11 0.9800 . ?
C11 C12 1.515(3) . ?
C12 C13 1.384(4) . ?
C12 C17 1.385(3) . ?
C13 H13 0.9300 . ?
C13 C14 1.384(4) . ?
C14 H14 0.9300 . ?
C14 C15 1.380(4) . ?
C15 C16 1.372(4) . ?
C16 H16 0.9300 . ?
C16 C17 1.384(4) . ?
C17 H17 0.9300 . ?
C18 C19 1.542(4) . ?
C18 C21 1.518(4) . ?
C18 C22 1.525(4) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C19 C20 1.509(4) . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 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
N2 N1 C9 102.91(16) . . ?
N2 N1 C18 102.12(17) . . ?
C9 N1 C18 120.64(19) . . ?
N1 N2 C11 112.76(17) . . ?
C20 N2 N1 113.22(19) . . ?
C20 N2 C11 132.1(2) . . ?
C2 C1 C6 120.5(2) . . ?
C2 C1 C9 128.1(2) . . ?
C6 C1 C9 111.4(2) . . ?
C1 C2 H2 120.8 . . ?
C1 C2 C3 118.4(3) . . ?
C3 C2 H2 120.8 . . ?
C2 C3 H3 119.5 . . ?
C4 C3 C2 121.0(3) . . ?
C4 C3 H3 119.5 . . ?
C3 C4 H4 119.7 . . ?
C3 C4 C5 120.5(3) . . ?
C5 C4 H4 119.7 . . ?
C4 C5 H5 120.6 . . ?
C6 C5 C4 118.9(3) . . ?
C6 C5 H5 120.6 . . ?
C1 C6 C7 111.5(2) . . ?
C5 C6 C1 120.6(3) . . ?
C5 C6 C7 127.8(3) . . ?
C6 C7 H7 120.5 . . ?
C6 C7 C8 104.7(2) . . ?
C8 C7 H7 120.5 . . ?
C10 C7 C6 115.8(2) . . ?
C10 C7 H7 120.5 . . ?
C10 C7 C8 57.31(15) . . ?
C9 C8 C7 107.30(18) . . ?
C10 C8 C7 58.38(16) . . ?
C10 C8 C9 120.3(2) . . ?
C10 C8 C11 125.3(2) . . ?
C11 C8 C7 124.9(2) . . ?
C11 C8 C9 110.15(18) . . ?
N1 C9 C1 112.76(19) . . ?
N1 C9 C8 100.30(17) . . ?
N1 C9 H9 112.7 . . ?
C1 C9 C8 104.70(19) . . ?
C1 C9 H9 112.7 . . ?
C8 C9 H9 112.7 . . ?
F1 C10 C7 121.4(2) . . ?
F1 C10 C8 121.5(2) . . ?
F2 C10 F1 108.2(2) . . ?
F2 C10 C7 118.1(2) . . ?
F2 C10 C8 118.0(2) . . ?
C8 C10 C7 64.31(16) . . ?
N2 C11 C8 99.30(17) . . ?
N2 C11 H11 109.9 . . ?
N2 C11 C12 111.30(18) . . ?
C8 C11 H11 109.9 . . ?
C12 C11 C8 116.18(19) . . ?
C12 C11 H11 109.9 . . ?
C13 C12 C11 121.6(2) . . ?
C13 C12 C17 118.7(2) . . ?
C17 C12 C11 119.6(2) . . ?
C12 C13 H13 119.5 . . ?
C14 C13 C12 121.0(2) . . ?
C14 C13 H13 119.5 . . ?
C13 C14 H14 120.6 . . ?
C15 C14 C13 118.7(3) . . ?
C15 C14 H14 120.6 . . ?
C14 C15 Br1 119.4(2) . . ?
C16 C15 Br1 119.0(2) . . ?
C16 C15 C14 121.5(3) . . ?
C15 C16 H16 120.5 . . ?
C15 C16 C17 119.0(3) . . ?
C17 C16 H16 120.5 . . ?
C12 C17 H17 119.5 . . ?
C16 C17 C12 121.0(3) . . ?
C16 C17 H17 119.5 . . ?
N1 C18 C19 100.2(2) . . ?
N1 C18 C21 109.1(2) . . ?
N1 C18 C22 113.1(2) . . ?
C21 C18 C19 111.7(2) . . ?
C21 C18 C22 111.6(3) . . ?
C22 C18 C19 110.7(2) . . ?
C18 C19 H19A 110.7 . . ?
C18 C19 H19B 110.7 . . ?
H19A C19 H19B 108.8 . . ?
C20 C19 C18 105.1(2) . . ?
C20 C19 H19A 110.7 . . ?
C20 C19 H19B 110.7 . . ?
O1 C20 N2 125.7(2) . . ?
O1 C20 C19 128.8(2) . . ?
N2 C20 C19 105.5(2) . . ?
C18 C21 H21A 109.5 . . ?
C18 C21 H21B 109.5 . . ?
C18 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C18 C22 H22A 109.5 . . ?
C18 C22 H22B 109.5 . . ?
C18 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 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 C15 C16 C17 179.2(2) . . . . ?
N1 N2 C11 C8 17.9(2) . . . . ?
N1 N2 C11 C12 140.81(19) . . . . ?
N1 N2 C20 O1 166.5(2) . . . . ?
N1 N2 C20 C19 -11.2(3) . . . . ?
N1 C18 C19 C20 30.6(3) . . . . ?
N2 N1 C9 C1 147.26(19) . . . . ?
N2 N1 C9 C8 36.4(2) . . . . ?
N2 N1 C18 C19 -35.9(2) . . . . ?
N2 N1 C18 C21 -153.2(2) . . . . ?
N2 N1 C18 C22 81.9(3) . . . . ?
N2 C11 C12 C13 -56.3(3) . . . . ?
N2 C11 C12 C17 122.9(2) . . . . ?
C1 C2 C3 C4 -2.1(4) . . . . ?
C1 C6 C7 C8 -0.3(3) . . . . ?
C1 C6 C7 C10 -60.8(3) . . . . ?
C2 C1 C6 C5 -2.1(4) . . . . ?
C2 C1 C6 C7 175.5(2) . . . . ?
C2 C1 C9 N1 78.9(3) . . . . ?
C2 C1 C9 C8 -173.1(2) . . . . ?
C2 C3 C4 C5 -0.4(5) . . . . ?
C3 C4 C5 C6 1.6(4) . . . . ?
C4 C5 C6 C1 -0.4(4) . . . . ?
C4 C5 C6 C7 -177.5(3) . . . . ?
C5 C6 C7 C8 177.1(3) . . . . ?
C5 C6 C7 C10 116.6(3) . . . . ?
C6 C1 C2 C3 3.3(4) . . . . ?
C6 C1 C9 N1 -102.1(2) . . . . ?
C6 C1 C9 C8 6.0(3) . . . . ?
C6 C7 C8 C9 4.0(2) . . . . ?
C6 C7 C8 C10 -111.4(2) . . . . ?
C6 C7 C8 C11 135.0(2) . . . . ?
C6 C7 C10 F1 -21.2(3) . . . . ?
C6 C7 C10 F2 -159.1(2) . . . . ?
C6 C7 C10 C8 91.5(2) . . . . ?
C7 C8 C9 N1 111.11(19) . . . . ?
C7 C8 C9 C1 -5.9(2) . . . . ?
C7 C8 C10 F1 112.5(3) . . . . ?
C7 C8 C10 F2 -109.7(3) . . . . ?
C7 C8 C11 N2 -122.8(2) . . . . ?
C7 C8 C11 C12 117.8(2) . . . . ?
C8 C7 C10 F1 -112.7(3) . . . . ?
C8 C7 C10 F2 109.5(2) . . . . ?
C8 C11 C12 C13 56.3(3) . . . . ?
C8 C11 C12 C17 -124.4(3) . . . . ?
C9 N1 N2 C11 -36.5(2) . . . . ?
C9 N1 N2 C20 157.1(2) . . . . ?
C9 N1 C18 C19 -149.0(2) . . . . ?
C9 N1 C18 C21 93.7(3) . . . . ?
C9 N1 C18 C22 -31.2(3) . . . . ?
C9 C1 C2 C3 -177.8(2) . . . . ?
C9 C1 C6 C5 178.8(2) . . . . ?
C9 C1 C6 C7 -3.6(3) . . . . ?
C9 C8 C10 F1 20.0(3) . . . . ?
C9 C8 C10 F2 157.8(2) . . . . ?
C9 C8 C10 C7 -92.5(2) . . . . ?
C9 C8 C11 N2 7.1(2) . . . . ?
C9 C8 C11 C12 -112.3(2) . . . . ?
C10 C7 C8 C9 115.4(2) . . . . ?
C10 C7 C8 C11 -113.5(3) . . . . ?
C10 C8 C9 N1 174.1(2) . . . . ?
C10 C8 C9 C1 57.1(3) . . . . ?
C10 C8 C11 N2 164.0(2) . . . . ?
C10 C8 C11 C12 44.6(3) . . . . ?
C11 N2 C20 O1 3.6(4) . . . . ?
C11 N2 C20 C19 -174.2(2) . . . . ?
C11 C8 C9 N1 -27.6(2) . . . . ?
C11 C8 C9 C1 -144.66(19) . . . . ?
C11 C8 C10 F1 -134.8(2) . . . . ?
C11 C8 C10 F2 3.0(4) . . . . ?
C11 C8 C10 C7 112.7(3) . . . . ?
C11 C12 C13 C14 179.9(2) . . . . ?
C11 C12 C17 C16 180.0(3) . . . . ?
C12 C13 C14 C15 0.0(4) . . . . ?
C13 C12 C17 C16 -0.8(4) . . . . ?
C13 C14 C15 Br1 -179.4(2) . . . . ?
C13 C14 C15 C16 -0.5(5) . . . . ?
C14 C15 C16 C17 0.4(5) . . . . ?
C15 C16 C17 C12 0.3(5) . . . . ?
C17 C12 C13 C14 0.6(4) . . . . ?
C18 N1 N2 C11 -162.22(19) . . . . ?
C18 N1 N2 C20 31.4(3) . . . . ?
C18 N1 C9 C1 -100.0(2) . . . . ?
C18 N1 C9 C8 149.1(2) . . . . ?
C18 C19 C20 O1 169.1(3) . . . . ?
C18 C19 C20 N2 -13.3(3) . . . . ?
C20 N2 C11 C8 -179.1(2) . . . . ?
C20 N2 C11 C12 -56.2(3) . . . . ?
C21 C18 C19 C20 146.0(3) . . . . ?
C22 C18 C19 C20 -89.0(3) . . . . ?

_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 1.298
_oxdiff_exptl_absorpt_empirical_full_min 0.707
