# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2020

####################################################################### 
# 
# 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_exp_280
_database_code_depnum_ccdc_archive 'CCDC 2021744'
loop_
_audit_author_name
_audit_author_address
'haipeng hu'
;sichuan normal university
China
;
_audit_update_record             
;
2020-08-06 deposited with the CCDC.	2020-09-27 downloaded from the CCDC.
;
_audit_creation_date             2020-07-28
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2019.04.23 svn.r3594 for Rigaku Oxford Diffraction, GUI svn.r5739)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H15 Br Cl N'
_chemical_formula_sum            'C23 H15 Br Cl N0.25'
_chemical_formula_weight         410.21
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C1 H1 Cl1 Br1 N1'
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'
Cl Cl 0.3639 0.7018 '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'

_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      orthorhombic
_space_group_IT_number           29
_space_group_name_H-M_alt        'P c a 21'
_space_group_name_Hall           'P 2c -2ac'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y, z'
'-x+1/2, y, z+1/2'

_cell_length_a                   8.52520(10)
_cell_length_b                   11.9586(2)
_cell_length_c                   17.5059(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1784.72(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5327
_cell_measurement_temperature    298.56(10)
_cell_measurement_theta_max      76.0180
_cell_measurement_theta_min      6.2480
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    4.519
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.47940
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.59a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.527
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             827
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0316
_diffrn_reflns_av_unetI/netI     0.0351
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.958
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            8560
_diffrn_reflns_point_group_measured_fraction_full 0.877
_diffrn_reflns_point_group_measured_fraction_max 0.824
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.614
_diffrn_reflns_theta_min         3.696
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      298.56(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.958
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     30.00 118.00   0.50    0.05    --   46.37  60.00 -23.00  176
  2  ω    -76.00 -29.00   0.50    0.15    -- -102.00  65.00-176.00   94
  3  ω     33.00 111.00   0.50    0.15    --  106.06-105.00 -38.00  156
  4  ω     33.00  80.00   0.50    0.15    --  106.06 -65.00  47.00   94
  5  ω     89.00 178.00   0.50    0.15    --  106.06  60.00 -23.00  178
  6  ω    -24.00  29.00   0.50    0.05    --  -46.37  19.00 -30.00  106
  7  ω    -24.00  29.00   0.50    0.05    --  -46.37  19.00 150.00  106
  8  ω   -118.00 -71.00   0.50    0.05    --  -46.37-125.00 -60.00   94
  9  ω     15.00  95.00   0.50    0.05    --   46.37-125.00 -90.00  160
 10  ω    -69.00 -29.00   0.50    0.15    -- -102.00  61.00  30.00   80
 11  ω    -69.00 -29.00   0.50    0.15    -- -102.00  61.00   0.00   80
 12  ω     33.00  73.00   0.50    0.15    --  106.06 -61.00  90.00   80
 13  ω     91.00 178.00   0.50    0.15    --  106.06  30.00 120.00  174
;
_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      -0.0619541000
_diffrn_orient_matrix_UB_12      -0.1209737000
_diffrn_orient_matrix_UB_13      0.0027878000
_diffrn_orient_matrix_UB_21      0.1206867000
_diffrn_orient_matrix_UB_22      -0.0283431000
_diffrn_orient_matrix_UB_23      0.0625772000
_diffrn_orient_matrix_UB_31      -0.1193710000
_diffrn_orient_matrix_UB_32      0.0341280000
_diffrn_orient_matrix_UB_33      0.0617898000
_diffrn_oxdiff_digest_frames     
;
01f6b57f71959c7d83ae10beea2f4e1f90001270a51
;
_diffrn_oxdiff_digest_hkl        
;
01a64f79f4594bb8d0f7d78d93fa3eb3f3cb88
;
_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         0.660
_reflns_Friedel_fraction_full    0.745
_reflns_Friedel_fraction_max     0.680
_reflns_number_gt                2842
_reflns_number_total             3105
_reflns_odcompleteness_completeness 99.84
_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 1.171.40.59a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.59a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.59a (Rigaku OD, 2019)'
_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         0.302
_refine_diff_density_min         -0.375
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details 
;
 Flack x determined using 1036 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.029(18)
_refine_ls_extinction_coef       0.00061(18)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.113
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         3105
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0387
_refine_ls_R_factor_gt           0.0360
_refine_ls_restrained_S_all      1.113
_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)+(0.0420P)²+0.4009P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0956
_refine_ls_wR_factor_ref         0.0978
_refine_special_details          ?
_olex2_refinement_description    
;
1. Others
 Fixed Uiso: H9(0.058) H22(0.067) H3(0.077) H20(0.066) H11(0.061) H19(0.061)
 H2(0.07) H13(0.076) H17(0.082) H23(0.066) H5(0.086) H6(0.074) H15(0.098)
 H16(0.098) H14(0.093)
 Fixed X: H9(0.7897) H22(0.4833) H3(0.9207) H20(0.4987) H11(1.0937)
 H19(0.6957) H2(0.8447) H13(1.0019) H17(1.0294) H23(0.682) H5(1.2513)
 H6(1.1741) H15(1.2123) H16(1.157) H14(1.1292)
 Fixed Y: H9(0.573) H22(0.1796) H3(0.8878) H20(0.4914) H11(0.39) H19(0.5353)
 H2(0.7272) H13(0.261) H17(0.1667) H23(0.2235) H5(0.7116) H6(0.5524) H15(-
 0.0263) H16(0.0054) H14(0.0991)
 Fixed Z: H9(0.4996) H22(0.6238) H3(0.3705) H20(0.7073) H11(0.3895)
 H19(0.6225) H2(0.435) H13(0.6162) H17(0.3971) H23(0.539) H5(0.2618) H6(0.3246)
 H15(0.5613) H16(0.4347) H14(0.6521)
;
_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 1.16512(9) 0.94724(6) 0.26204(4) 0.0954(3) Uani 1 1 d . . . . .
Cl Cl 0.32401(14) 0.29756(14) 0.73771(7) 0.0712(4) Uani 1 1 d . . . . .
N1 N 0.8447(4) 0.5166(3) 0.4851(2) 0.0486(8) Uani 1 1 d . . . . .
H9 H 0.7897 0.5730 0.4996 0.058 Uiso 1 1 calc R . . . .
C11 C 0.7120(4) 0.3848(3) 0.5714(2) 0.0463(8) Uani 1 1 d . . . . .
C17 C 1.0045(5) 0.2338(4) 0.5024(3) 0.0525(10) Uani 1 1 d . . . . .
C4 C 0.9997(5) 0.6216(4) 0.3873(3) 0.0494(9) Uani 1 1 d . . . . .
C9 C 0.9462(4) 0.3451(4) 0.4797(3) 0.0480(9) Uani 1 1 d . . . . .
C10 C 0.8339(4) 0.4116(4) 0.5159(3) 0.0481(9) Uani 1 1 d . . . . .
C14 C 0.4727(5) 0.3315(4) 0.6731(2) 0.0533(10) Uani 1 1 d . . . . .
C7 C 0.9560(5) 0.5199(4) 0.4276(2) 0.0483(9) Uani 1 1 d . . . . .
C15 C 0.5264(5) 0.2510(4) 0.6234(3) 0.0562(11) Uani 1 1 d . . . . .
H22 H 0.4833 0.1796 0.6238 0.067 Uiso 1 1 calc R . . . .
C6 C 0.9720(6) 0.8204(4) 0.3618(3) 0.0645(12) Uani 1 1 d . . . . .
H3 H 0.9207 0.8878 0.3705 0.077 Uiso 1 1 calc R . . . .
C13 C 0.5356(5) 0.4378(4) 0.6733(3) 0.0551(11) Uani 1 1 d . . . . .
H20 H 0.4987 0.4914 0.7073 0.066 Uiso 1 1 calc R . . . .
C8 C 1.0171(5) 0.4134(4) 0.4238(3) 0.0505(9) Uani 1 1 d . . . . .
H11 H 1.0937 0.3900 0.3895 0.061 Uiso 1 1 calc R . . . .
C12 C 0.6538(5) 0.4635(4) 0.6226(3) 0.0512(10) Uani 1 1 d . . . . .
H19 H 0.6957 0.5353 0.6225 0.061 Uiso 1 1 calc R . . . .
C1 C 1.0942(6) 0.8140(5) 0.3113(3) 0.0644(13) Uani 1 1 d . . . . .
C5 C 0.9265(5) 0.7235(4) 0.4000(3) 0.0580(11) Uani 1 1 d . . . . .
H2 H 0.8447 0.7272 0.4350 0.070 Uiso 1 1 calc R . . . .
C22 C 1.0341(6) 0.2105(4) 0.5789(3) 0.0634(12) Uani 1 1 d . . . . .
H13 H 1.0019 0.2610 0.6162 0.076 Uiso 1 1 calc R . . . .
C18 C 1.0503(7) 0.1546(4) 0.4486(3) 0.0680(13) Uani 1 1 d . . . . .
H17 H 1.0294 0.1667 0.3971 0.082 Uiso 1 1 calc R . . . .
C16 C 0.6456(5) 0.2777(4) 0.5727(3) 0.0550(10) Uani 1 1 d . . . . .
H23 H 0.6820 0.2235 0.5390 0.066 Uiso 1 1 calc R . . . .
C2 C 1.1694(6) 0.7145(6) 0.2968(3) 0.0716(15) Uani 1 1 d . . . . .
H5 H 1.2513 0.7116 0.2618 0.086 Uiso 1 1 calc R . . . .
C3 C 1.1229(6) 0.6196(5) 0.3344(3) 0.0620(12) Uani 1 1 d . . . . .
H6 H 1.1741 0.5524 0.3246 0.074 Uiso 1 1 calc R . . . .
C20 C 1.1585(7) 0.0379(5) 0.5468(5) 0.0816(19) Uani 1 1 d . . . . .
H15 H 1.2123 -0.0263 0.5613 0.098 Uiso 1 1 calc R . . . .
C19 C 1.1268(8) 0.0576(4) 0.4712(5) 0.0819(18) Uani 1 1 d . . . . .
H16 H 1.1570 0.0054 0.4347 0.098 Uiso 1 1 calc R . . . .
C21 C 1.1105(7) 0.1132(5) 0.6006(4) 0.0773(15) Uani 1 1 d . . . . .
H14 H 1.1292 0.0991 0.6521 0.093 Uiso 1 1 calc R . . . .


_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 1.909(5) . ?
Cl C14 1.746(4) . ?
N1 H9 0.8600 . ?
N1 C10 1.370(6) . ?
N1 C7 1.383(6) . ?
C11 C10 1.458(6) . ?
C11 C12 1.391(6) . ?
C11 C16 1.401(6) . ?
C17 C9 1.476(7) . ?
C17 C22 1.392(7) . ?
C17 C18 1.392(7) . ?
C4 C7 1.455(7) . ?
C4 C5 1.386(7) . ?
C4 C3 1.400(7) . ?
C9 C10 1.397(6) . ?
C9 C8 1.410(6) . ?
C14 C15 1.375(7) . ?
C14 C13 1.380(7) . ?
C7 C8 1.377(7) . ?
C15 H22 0.9300 . ?
C15 C16 1.386(7) . ?
C6 H3 0.9300 . ?
C6 C1 1.369(8) . ?
C6 C5 1.393(7) . ?
C13 H20 0.9300 . ?
C13 C12 1.378(7) . ?
C8 H11 0.9300 . ?
C12 H19 0.9300 . ?
C1 C2 1.376(9) . ?
C5 H2 0.9300 . ?
C22 H13 0.9300 . ?
C22 C21 1.386(8) . ?
C18 H17 0.9300 . ?
C18 C19 1.389(9) . ?
C16 H23 0.9300 . ?
C2 H5 0.9300 . ?
C2 C3 1.371(8) . ?
C3 H6 0.9300 . ?
C20 H15 0.9300 . ?
C20 C19 1.371(11) . ?
C20 C21 1.366(10) . ?
C19 H16 0.9300 . ?
C21 H14 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
C10 N1 H9 124.5 . . ?
C10 N1 C7 111.0(4) . . ?
C7 N1 H9 124.5 . . ?
C12 C11 C10 122.3(4) . . ?
C12 C11 C16 117.6(4) . . ?
C16 C11 C10 120.0(4) . . ?
C22 C17 C9 120.1(4) . . ?
C18 C17 C9 121.8(5) . . ?
C18 C17 C22 117.7(5) . . ?
C5 C4 C7 122.8(4) . . ?
C5 C4 C3 117.3(4) . . ?
C3 C4 C7 119.8(4) . . ?
C10 C9 C17 128.5(4) . . ?
C10 C9 C8 106.2(4) . . ?
C8 C9 C17 124.3(4) . . ?
N1 C10 C11 120.8(4) . . ?
N1 C10 C9 107.3(4) . . ?
C9 C10 C11 131.7(4) . . ?
C15 C14 Cl 119.3(4) . . ?
C15 C14 C13 121.1(4) . . ?
C13 C14 Cl 119.6(4) . . ?
N1 C7 C4 123.5(4) . . ?
C8 C7 N1 105.6(4) . . ?
C8 C7 C4 130.8(4) . . ?
C14 C15 H22 120.4 . . ?
C14 C15 C16 119.2(4) . . ?
C16 C15 H22 120.4 . . ?
C1 C6 H3 120.8 . . ?
C1 C6 C5 118.4(5) . . ?
C5 C6 H3 120.8 . . ?
C14 C13 H20 120.4 . . ?
C12 C13 C14 119.2(4) . . ?
C12 C13 H20 120.4 . . ?
C9 C8 H11 125.1 . . ?
C7 C8 C9 109.8(4) . . ?
C7 C8 H11 125.1 . . ?
C11 C12 H19 119.2 . . ?
C13 C12 C11 121.7(4) . . ?
C13 C12 H19 119.2 . . ?
C6 C1 Br1 119.1(4) . . ?
C6 C1 C2 121.4(5) . . ?
C2 C1 Br1 119.5(4) . . ?
C4 C5 C6 122.0(4) . . ?
C4 C5 H2 119.0 . . ?
C6 C5 H2 119.0 . . ?
C17 C22 H13 119.4 . . ?
C21 C22 C17 121.1(5) . . ?
C21 C22 H13 119.4 . . ?
C17 C18 H17 119.8 . . ?
C19 C18 C17 120.5(6) . . ?
C19 C18 H17 119.8 . . ?
C11 C16 H23 119.4 . . ?
C15 C16 C11 121.1(4) . . ?
C15 C16 H23 119.4 . . ?
C1 C2 H5 120.2 . . ?
C3 C2 C1 119.6(5) . . ?
C3 C2 H5 120.2 . . ?
C4 C3 H6 119.3 . . ?
C2 C3 C4 121.3(5) . . ?
C2 C3 H6 119.3 . . ?
C19 C20 H15 120.2 . . ?
C21 C20 H15 120.2 . . ?
C21 C20 C19 119.6(6) . . ?
C18 C19 H16 119.6 . . ?
C20 C19 C18 120.8(6) . . ?
C20 C19 H16 119.6 . . ?
C22 C21 H14 119.8 . . ?
C20 C21 C22 120.3(7) . . ?
C20 C21 H14 119.8 . . ?

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 177.4(4) . . . . ?
Cl C14 C15 C16 -179.3(4) . . . . ?
Cl C14 C13 C12 179.4(4) . . . . ?
N1 C7 C8 C9 -1.2(5) . . . . ?
C17 C9 C10 N1 166.1(4) . . . . ?
C17 C9 C10 C11 -19.1(8) . . . . ?
C17 C9 C8 C7 -167.1(4) . . . . ?
C17 C22 C21 C20 0.0(9) . . . . ?
C17 C18 C19 C20 0.1(9) . . . . ?
C4 C7 C8 C9 174.0(4) . . . . ?
C9 C17 C22 C21 -170.3(5) . . . . ?
C9 C17 C18 C19 170.1(5) . . . . ?
C10 N1 C7 C4 -176.4(4) . . . . ?
C10 N1 C7 C8 -0.8(5) . . . . ?
C10 C11 C12 C13 178.2(4) . . . . ?
C10 C11 C16 C15 -178.1(4) . . . . ?
C10 C9 C8 C7 2.7(5) . . . . ?
C14 C15 C16 C11 0.1(7) . . . . ?
C14 C13 C12 C11 -0.4(7) . . . . ?
C7 N1 C10 C11 -173.0(4) . . . . ?
C7 N1 C10 C9 2.5(5) . . . . ?
C7 C4 C5 C6 178.7(4) . . . . ?
C7 C4 C3 C2 -178.4(5) . . . . ?
C15 C14 C13 C12 0.3(7) . . . . ?
C6 C1 C2 C3 -0.8(8) . . . . ?
C13 C14 C15 C16 -0.2(7) . . . . ?
C8 C9 C10 N1 -3.1(5) . . . . ?
C8 C9 C10 C11 171.7(4) . . . . ?
C12 C11 C10 N1 -31.9(6) . . . . ?
C12 C11 C10 C9 153.9(5) . . . . ?
C12 C11 C16 C15 -0.3(7) . . . . ?
C1 C6 C5 C4 -0.9(8) . . . . ?
C1 C2 C3 C4 0.2(8) . . . . ?
C5 C4 C7 N1 -3.9(6) . . . . ?
C5 C4 C7 C8 -178.3(4) . . . . ?
C5 C4 C3 C2 0.1(7) . . . . ?
C5 C6 C1 Br1 -177.0(4) . . . . ?
C5 C6 C1 C2 1.2(8) . . . . ?
C22 C17 C9 C10 -41.0(7) . . . . ?
C22 C17 C9 C8 126.4(5) . . . . ?
C22 C17 C18 C19 -1.9(7) . . . . ?
C18 C17 C9 C10 147.2(5) . . . . ?
C18 C17 C9 C8 -45.4(7) . . . . ?
C18 C17 C22 C21 1.9(8) . . . . ?
C16 C11 C10 N1 145.9(4) . . . . ?
C16 C11 C10 C9 -28.3(7) . . . . ?
C16 C11 C12 C13 0.4(7) . . . . ?
C3 C4 C7 N1 174.5(4) . . . . ?
C3 C4 C7 C8 0.1(7) . . . . ?
C3 C4 C5 C6 0.3(7) . . . . ?
C19 C20 C21 C22 -1.8(10) . . . . ?
C21 C20 C19 C18 1.7(10) . . . . ?

_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 1.825
_oxdiff_exptl_absorpt_empirical_full_min 0.699
