# 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_5-k1b
_database_code_depnum_ccdc_archive 'CCDC 2328278'
loop_
_audit_author_name
_audit_author_address
'Wenzhe Li'
;University of Chinese Academy of Sciences
China
;
_audit_update_record             
;
2024-01-25 deposited with the CCDC.	2024-03-11 downloaded from the CCDC.
;
_audit_creation_date             2022-10-13
_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         'C25 H14 Br F3 N2 O'
_chemical_formula_sum            'C25 H14 Br F3 N2 O'
_chemical_formula_weight         495.29
_chemical_absolute_configuration ad
_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      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                   9.6192(6)
_cell_length_b                   11.1853(7)
_cell_length_c                   9.6445(8)
_cell_angle_alpha                90
_cell_angle_beta                 94.316(6)
_cell_angle_gamma                90
_cell_volume                     1034.75(12)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5180
_cell_measurement_temperature    211(50)
_cell_measurement_theta_max      73.2780
_cell_measurement_theta_min      3.9470
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    3.131
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.53894
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'light colourless'
_exptl_crystal_density_diffrn    1.590
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             496
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.09
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0425
_diffrn_reflns_av_unetI/netI     0.0348
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            5851
_diffrn_reflns_point_group_measured_fraction_full 0.779
_diffrn_reflns_point_group_measured_fraction_max 0.749
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.731
_diffrn_reflns_theta_min         4.598
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      211(50)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -115.00 -16.00   1.00    1.00    --  -40.73 -38.00-180.00   99
  2  ω     23.00  97.00   1.00    1.00    --   40.73-125.00 150.00   74
  3  ω    -31.00  69.00   1.00    1.00    --   40.73 -57.00-180.00  100
  4  ω     38.00 130.00   1.00    1.00    --  107.58 -45.00  90.00   92
  5  ω    111.00 157.00   1.00    1.00    --  107.58 125.00 120.00   46
  6  ω     27.00 109.00   1.00    1.00    --  107.58 -94.00 -90.00   82
  7  ω    136.00 167.00   1.00    1.00    --  107.58 125.00 -30.00   31
  8  ω     80.00 173.00   1.00    1.00    --  107.58  30.00  30.00   93
  9  ω     73.00 106.00   1.00    1.00    --  107.58 -94.00  60.00   33
 10  ω    -57.00  26.00   1.00    1.00    --  -40.98  38.00   0.00   83
 11  ω     21.00 111.00   1.00    1.00    --   40.98  57.00  90.00   90
 12  ω     36.00  65.00   1.00    1.00    --   40.98-125.00  30.00   29
 13  ω    151.00 178.00   1.00    1.00    --  106.95  45.00  90.00   27
 14  ω     81.00 129.00   1.00    1.00    --  106.95 -61.00 -60.00   48
 15  ω     85.00 150.00   1.00    1.00    --  106.95  77.00 -90.00   65
 16  ω     35.00  64.00   1.00    1.00    --  106.95 -61.00 -60.00   29
 17  ω     99.00 125.00   1.00    1.00    --  106.95 125.00  30.00   26
 18  ω    150.00 176.00   1.00    1.00    --  106.95 125.00  30.00   26
 19  ω     74.00 100.00   1.00    1.00    --  106.95 -94.00   0.00   26
 20  ω     77.00 119.00   1.00    1.00    --  106.95-125.00-150.00   42
 21  ω    113.00 138.00   1.00    1.00    --  106.95  45.00 -30.00   25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1455274000
_diffrn_orient_matrix_UB_12      0.0428205000
_diffrn_orient_matrix_UB_13      0.0569548000
_diffrn_orient_matrix_UB_21      0.0516789000
_diffrn_orient_matrix_UB_22      -0.0087716000
_diffrn_orient_matrix_UB_23      -0.1469949000
_diffrn_orient_matrix_UB_31      -0.0441942000
_diffrn_orient_matrix_UB_32      0.1306055000
_diffrn_orient_matrix_UB_33      -0.0287710000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.464
_reflns_Friedel_fraction_full    0.536
_reflns_Friedel_fraction_max     0.502
_reflns_number_gt                3003
_reflns_number_total             3131
_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 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_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    'SHELXS  (Sheldrick, 2008)'
_refine_diff_density_max         0.729
_refine_diff_density_min         -1.501
_refine_diff_density_rms         0.099
_refine_ls_abs_structure_details 
;
 Flack x determined using 895 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.12(3)
_refine_ls_extinction_coef       0.0068(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2017/1 (Sheldrick 2017)'
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     290
_refine_ls_number_reflns         3131
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0537
_refine_ls_R_factor_gt           0.0507
_refine_ls_restrained_S_all      1.080
_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)+(0.0743P)²+3.4144P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1451
_refine_ls_wR_factor_ref         0.1517
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N1(H1), C5(H5), C2(H2), C4(H4), C10(H10), C14(H14), C3(H3), C17(H17),
 C15(H15), C16(H16), C24(H24), C21(H21), C23(H23), C20(H20)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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 -0.07368(7) 0.87490(10) 0.09499(9) 0.0412(3) Uani 1 1 d . . . . .
F1 F 0.2508(6) 0.5735(8) 0.6798(7) 0.0616(19) Uani 1 1 d . . . . .
F3 F 0.4593(7) 0.6333(8) 0.7310(7) 0.069(2) Uani 1 1 d . . . . .
N2 N 0.4858(6) 0.6235(6) 0.1955(7) 0.0258(14) Uani 1 1 d . . . . .
O1 O 0.6052(6) 0.7176(6) 0.0288(7) 0.0371(15) Uani 1 1 d . . . . .
F2 F 0.4040(8) 0.4482(7) 0.7521(7) 0.0667(19) Uani 1 1 d . . . . .
N1 N 0.3485(6) 0.3484(6) 0.2237(6) 0.0265(15) Uani 1 1 d . . . . .
H1 H 0.367223 0.336824 0.136796 0.032 Uiso 1 1 calc R U . . .
C19 C 0.3547(7) 0.6844(7) 0.1706(8) 0.0255(16) Uani 1 1 d . . . . .
C5 C 0.1830(8) 0.1797(8) 0.2579(10) 0.0346(19) Uani 1 1 d . . . . .
H5 H 0.186095 0.146809 0.167305 0.042 Uiso 1 1 calc R U . . .
C2 C 0.1754(8) 0.2737(8) 0.5296(9) 0.0298(18) Uani 1 1 d . . . . .
H2 H 0.172752 0.304387 0.621234 0.036 Uiso 1 1 calc R U . . .
C22 C 0.1020(8) 0.7990(8) 0.1240(9) 0.0282(17) Uani 1 1 d . . . . .
C11 C 0.5101(8) 0.5347(8) 0.3072(9) 0.0266(16) Uani 1 1 d . . . . .
C13 C 0.7092(8) 0.5620(8) 0.1799(9) 0.0287(17) Uani 1 1 d . . . . .
C6 C 0.2595(8) 0.2803(8) 0.2977(8) 0.0258(16) Uani 1 1 d . . . . .
C4 C 0.1019(9) 0.1286(9) 0.3543(12) 0.042(2) Uani 1 1 d . . . . .
H4 H 0.046603 0.060680 0.328361 0.050 Uiso 1 1 calc R U . . .
C8 C 0.3497(8) 0.4294(7) 0.4387(8) 0.0259(16) Uani 1 1 d . . . . .
C18 C 0.5995(7) 0.6446(8) 0.1211(9) 0.0279(17) Uani 1 1 d . . . . .
C1 C 0.2570(7) 0.3294(7) 0.4353(8) 0.0254(16) Uani 1 1 d . . . . .
C12 C 0.6568(8) 0.4935(8) 0.2828(9) 0.0285(17) Uani 1 1 d . . . . .
C10 C 0.5054(7) 0.5851(8) 0.4540(8) 0.0252(16) Uani 1 1 d . . . . .
H10 H 0.558710 0.651336 0.489671 0.030 Uiso 1 1 calc R U . . .
C14 C 0.8463(8) 0.5484(9) 0.1469(10) 0.0345(19) Uani 1 1 d . . . . .
H14 H 0.882696 0.594723 0.075505 0.041 Uiso 1 1 calc R U . . .
C3 C 0.0991(8) 0.1745(8) 0.4899(10) 0.0332(18) Uani 1 1 d . . . . .
H3 H 0.043852 0.136281 0.554443 0.040 Uiso 1 1 calc R U . . .
C9 C 0.4160(7) 0.5231(8) 0.5252(8) 0.0256(16) Uani 1 1 d . . . . .
C17 C 0.7363(9) 0.4083(8) 0.3544(9) 0.037(2) Uani 1 1 d . . . . .
H17 H 0.699178 0.360499 0.424160 0.044 Uiso 1 1 calc R U . . .
C7 C 0.4016(7) 0.4357(7) 0.3087(8) 0.0239(15) Uani 1 1 d . . . . .
C15 C 0.9285(9) 0.4653(10) 0.2211(11) 0.044(2) Uani 1 1 d . . . . .
H15 H 1.023742 0.456902 0.203202 0.052 Uiso 1 1 calc R U . . .
C25 C 0.3855(9) 0.5436(9) 0.6730(10) 0.038(2) Uani 1 1 d . . . . .
C16 C 0.8739(9) 0.3950(10) 0.3202(10) 0.041(2) Uani 1 1 d . . . . .
H16 H 0.931107 0.335892 0.366577 0.050 Uiso 1 1 calc R U . . .
C24 C 0.3060(11) 0.7569(11) 0.2699(12) 0.053(3) Uani 1 1 d . . . . .
H24 H 0.361661 0.770234 0.354038 0.064 Uiso 1 1 calc R U . . .
C21 C 0.1514(9) 0.7278(10) 0.0217(11) 0.044(2) Uani 1 1 d . . . . .
H21 H 0.098120 0.718032 -0.064613 0.053 Uiso 1 1 calc R U . . .
C23 C 0.1766(11) 0.8113(11) 0.2501(12) 0.055(3) Uani 1 1 d . . . . .
H23 H 0.140211 0.856333 0.322610 0.066 Uiso 1 1 calc R U . . .
C20 C 0.2781(9) 0.6709(9) 0.0449(9) 0.036(2) Uani 1 1 d . . . . .
H20 H 0.312565 0.622330 -0.025685 0.044 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 C22 1.893(8) . ?
F1 C25 1.344(11) . ?
F3 C25 1.328(11) . ?
N2 C19 1.437(9) . ?
N2 C11 1.471(11) . ?
N2 C18 1.373(10) . ?
O1 C18 1.212(10) . ?
F2 C25 1.317(12) . ?
N1 H1 0.8800 . ?
N1 C6 1.383(10) . ?
N1 C7 1.351(10) . ?
C19 C24 1.365(13) . ?
C19 C20 1.379(12) . ?
C5 H5 0.9500 . ?
C5 C6 1.383(12) . ?
C5 C4 1.382(14) . ?
C2 H2 0.9500 . ?
C2 C1 1.393(12) . ?
C2 C3 1.369(13) . ?
C22 C21 1.379(13) . ?
C22 C23 1.372(13) . ?
C11 C12 1.520(10) . ?
C11 C10 1.528(11) . ?
C11 C7 1.523(11) . ?
C13 C18 1.482(11) . ?
C13 C12 1.379(12) . ?
C13 C14 1.388(11) . ?
C6 C1 1.438(11) . ?
C4 H4 0.9500 . ?
C4 C3 1.407(14) . ?
C8 C1 1.429(11) . ?
C8 C9 1.457(11) . ?
C8 C7 1.386(10) . ?
C12 C17 1.374(12) . ?
C10 H10 0.9500 . ?
C10 C9 1.335(11) . ?
C14 H14 0.9500 . ?
C14 C15 1.383(14) . ?
C3 H3 0.9500 . ?
C9 C25 1.494(12) . ?
C17 H17 0.9500 . ?
C17 C16 1.396(12) . ?
C15 H15 0.9500 . ?
C15 C16 1.372(15) . ?
C16 H16 0.9500 . ?
C24 H24 0.9500 . ?
C24 C23 1.385(13) . ?
C21 H21 0.9500 . ?
C21 C20 1.378(12) . ?
C23 H23 0.9500 . ?
C20 H20 0.9500 . ?

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
C19 N2 C11 122.1(6) . . ?
C18 N2 C19 123.7(7) . . ?
C18 N2 C11 114.1(6) . . ?
C6 N1 H1 126.1 . . ?
C7 N1 H1 126.1 . . ?
C7 N1 C6 107.8(6) . . ?
C24 C19 N2 120.5(7) . . ?
C24 C19 C20 119.5(8) . . ?
C20 C19 N2 120.0(7) . . ?
C6 C5 H5 121.1 . . ?
C6 C5 C4 117.7(9) . . ?
C4 C5 H5 121.1 . . ?
C1 C2 H2 120.1 . . ?
C3 C2 H2 120.1 . . ?
C3 C2 C1 119.8(8) . . ?
C21 C22 Br1 120.3(6) . . ?
C23 C22 Br1 119.2(7) . . ?
C23 C22 C21 120.5(8) . . ?
N2 C11 C12 101.0(6) . . ?
N2 C11 C10 114.5(7) . . ?
N2 C11 C7 115.3(6) . . ?
C12 C11 C10 110.4(6) . . ?
C12 C11 C7 115.2(7) . . ?
C7 C11 C10 101.0(6) . . ?
C12 C13 C18 109.5(7) . . ?
C12 C13 C14 120.5(8) . . ?
C14 C13 C18 129.9(8) . . ?
N1 C6 C1 108.6(7) . . ?
C5 C6 N1 129.9(8) . . ?
C5 C6 C1 121.4(8) . . ?
C5 C4 H4 119.1 . . ?
C5 C4 C3 121.7(8) . . ?
C3 C4 H4 119.1 . . ?
C1 C8 C9 145.3(7) . . ?
C7 C8 C1 106.6(7) . . ?
C7 C8 C9 108.0(7) . . ?
N2 C18 C13 105.4(7) . . ?
O1 C18 N2 125.5(7) . . ?
O1 C18 C13 129.1(7) . . ?
C2 C1 C6 118.8(7) . . ?
C2 C1 C8 135.8(8) . . ?
C8 C1 C6 105.4(7) . . ?
C13 C12 C11 109.6(7) . . ?
C17 C12 C11 128.4(8) . . ?
C17 C12 C13 121.9(8) . . ?
C11 C10 H10 124.7 . . ?
C9 C10 C11 110.5(7) . . ?
C9 C10 H10 124.7 . . ?
C13 C14 H14 120.9 . . ?
C15 C14 C13 118.1(8) . . ?
C15 C14 H14 120.9 . . ?
C2 C3 C4 120.6(8) . . ?
C2 C3 H3 119.7 . . ?
C4 C3 H3 119.7 . . ?
C8 C9 C25 123.2(7) . . ?
C10 C9 C8 110.5(7) . . ?
C10 C9 C25 126.3(8) . . ?
C12 C17 H17 121.4 . . ?
C12 C17 C16 117.2(8) . . ?
C16 C17 H17 121.4 . . ?
N1 C7 C11 138.4(7) . . ?
N1 C7 C8 111.5(7) . . ?
C8 C7 C11 109.9(7) . . ?
C14 C15 H15 119.6 . . ?
C16 C15 C14 120.8(8) . . ?
C16 C15 H15 119.6 . . ?
F1 C25 C9 110.1(8) . . ?
F3 C25 F1 106.2(8) . . ?
F3 C25 C9 112.4(7) . . ?
F2 C25 F1 105.2(8) . . ?
F2 C25 F3 108.9(9) . . ?
F2 C25 C9 113.6(8) . . ?
C17 C16 H16 119.3 . . ?
C15 C16 C17 121.5(9) . . ?
C15 C16 H16 119.3 . . ?
C19 C24 H24 119.4 . . ?
C19 C24 C23 121.1(9) . . ?
C23 C24 H24 119.4 . . ?
C22 C21 H21 120.1 . . ?
C20 C21 C22 119.9(9) . . ?
C20 C21 H21 120.1 . . ?
C22 C23 C24 118.8(9) . . ?
C22 C23 H23 120.6 . . ?
C24 C23 H23 120.6 . . ?
C19 C20 H20 120.0 . . ?
C21 C20 C19 120.0(8) . . ?
C21 C20 H20 120.0 . . ?

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 C22 C21 C20 -178.6(8) . . . . ?
Br1 C22 C23 C24 -179.1(10) . . . . ?
N2 C19 C24 C23 -176.7(11) . . . . ?
N2 C19 C20 C21 179.0(9) . . . . ?
N2 C11 C12 C13 5.9(9) . . . . ?
N2 C11 C12 C17 -178.8(9) . . . . ?
N2 C11 C10 C9 126.7(7) . . . . ?
N2 C11 C7 N1 59.2(13) . . . . ?
N2 C11 C7 C8 -126.3(7) . . . . ?
N1 C6 C1 C2 -178.9(7) . . . . ?
N1 C6 C1 C8 -0.3(8) . . . . ?
C19 N2 C11 C12 176.6(7) . . . . ?
C19 N2 C11 C10 -64.8(10) . . . . ?
C19 N2 C11 C7 51.8(11) . . . . ?
C19 N2 C18 O1 1.8(14) . . . . ?
C19 N2 C18 C13 -179.2(7) . . . . ?
C19 C24 C23 C22 -5(2) . . . . ?
C5 C6 C1 C2 0.0(11) . . . . ?
C5 C6 C1 C8 178.6(7) . . . . ?
C5 C4 C3 C2 1.4(13) . . . . ?
C22 C21 C20 C19 0.5(16) . . . . ?
C11 N2 C19 C24 62.3(12) . . . . ?
C11 N2 C19 C20 -118.4(10) . . . . ?
C11 N2 C18 O1 -176.6(8) . . . . ?
C11 N2 C18 C13 2.4(10) . . . . ?
C11 C12 C17 C16 -173.8(8) . . . . ?
C11 C10 C9 C8 -1.3(9) . . . . ?
C11 C10 C9 C25 178.5(8) . . . . ?
C13 C12 C17 C16 1.0(13) . . . . ?
C13 C14 C15 C16 2.8(15) . . . . ?
C6 N1 C7 C11 173.9(9) . . . . ?
C6 N1 C7 C8 -0.6(9) . . . . ?
C6 C5 C4 C3 -1.7(13) . . . . ?
C4 C5 C6 N1 179.7(8) . . . . ?
C4 C5 C6 C1 1.0(12) . . . . ?
C8 C9 C25 F1 -62.4(11) . . . . ?
C8 C9 C25 F3 179.4(8) . . . . ?
C8 C9 C25 F2 55.2(11) . . . . ?
C18 N2 C19 C24 -115.9(11) . . . . ?
C18 N2 C19 C20 63.4(12) . . . . ?
C18 N2 C11 C12 -5.0(9) . . . . ?
C18 N2 C11 C10 113.5(8) . . . . ?
C18 N2 C11 C7 -129.9(7) . . . . ?
C18 C13 C12 C11 -4.9(10) . . . . ?
C18 C13 C12 C17 179.4(8) . . . . ?
C18 C13 C14 C15 178.5(9) . . . . ?
C1 C2 C3 C4 -0.3(12) . . . . ?
C1 C8 C9 C10 175.4(11) . . . . ?
C1 C8 C9 C25 -4.3(17) . . . . ?
C1 C8 C7 N1 0.4(9) . . . . ?
C1 C8 C7 C11 -175.8(6) . . . . ?
C12 C11 C10 C9 -120.2(8) . . . . ?
C12 C11 C7 N1 -57.9(13) . . . . ?
C12 C11 C7 C8 116.7(8) . . . . ?
C12 C13 C18 N2 1.7(10) . . . . ?
C12 C13 C18 O1 -179.4(9) . . . . ?
C12 C13 C14 C15 -0.7(14) . . . . ?
C12 C17 C16 C15 1.1(15) . . . . ?
C10 C11 C12 C13 -115.7(8) . . . . ?
C10 C11 C12 C17 59.6(12) . . . . ?
C10 C11 C7 N1 -176.8(9) . . . . ?
C10 C11 C7 C8 -2.3(8) . . . . ?
C10 C9 C25 F1 117.8(10) . . . . ?
C10 C9 C25 F3 -0.3(14) . . . . ?
C10 C9 C25 F2 -124.5(9) . . . . ?
C14 C13 C18 N2 -177.6(9) . . . . ?
C14 C13 C18 O1 1.4(16) . . . . ?
C14 C13 C12 C11 174.5(8) . . . . ?
C14 C13 C12 C17 -1.2(13) . . . . ?
C14 C15 C16 C17 -3.1(16) . . . . ?
C3 C2 C1 C6 -0.4(11) . . . . ?
C3 C2 C1 C8 -178.5(8) . . . . ?
C9 C8 C1 C2 2.5(19) . . . . ?
C9 C8 C1 C6 -175.7(11) . . . . ?
C9 C8 C7 N1 177.8(7) . . . . ?
C9 C8 C7 C11 1.7(9) . . . . ?
C7 N1 C6 C5 -178.3(8) . . . . ?
C7 N1 C6 C1 0.6(8) . . . . ?
C7 C11 C12 C13 130.7(8) . . . . ?
C7 C11 C12 C17 -54.0(12) . . . . ?
C7 C11 C10 C9 2.1(9) . . . . ?
C7 C8 C1 C2 178.2(9) . . . . ?
C7 C8 C1 C6 0.0(8) . . . . ?
C7 C8 C9 C10 -0.2(10) . . . . ?
C7 C8 C9 C25 -180.0(8) . . . . ?
C24 C19 C20 C21 -1.7(15) . . . . ?
C21 C22 C23 C24 3.8(18) . . . . ?
C23 C22 C21 C20 -1.6(16) . . . . ?
C20 C19 C24 C23 4.1(18) . . . . ?

_olex2_date_sample_data_collection 2022-10-13
_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 2.792
_oxdiff_exptl_absorpt_empirical_full_min 0.672
