# Supplementary Information (SI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2026

####################################################################### 
# 
# 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_251202_5aa
_database_code_depnum_ccdc_archive 'CCDC 2519485'
loop_
_audit_author_name
_audit_author_address
'Takashi Koike'
;Nippon Institute of Technology
Japan
;
_audit_update_record             
;
2025-12-30 deposited with the CCDC.	2026-03-09 downloaded from the CCDC.
;
_audit_creation_date             2025-12-17
_audit_creation_method           
;
Olex2 1.5
(compiled 2025.07.13 svn.rb7424aed for OlexSys, GUI svn.r7314)
;
_shelx_SHELXL_version_number     2019/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H5 Cl F9 N'
_chemical_formula_sum            'C12 H5 Cl F9 N'
_chemical_formula_weight         369.62
_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'
Cl Cl 0.3639 0.7018 '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'

_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           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   11.5848(3)
_cell_length_b                   7.2834(2)
_cell_length_c                   32.0201(8)
_cell_angle_alpha                90
_cell_angle_beta                 96.310(2)
_cell_angle_gamma                90
_cell_volume                     2685.38(12)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    5245
_cell_measurement_temperature    223.15
_cell_measurement_theta_max      72.7840
_cell_measurement_theta_min      5.3200
_cell_oxdiff_angle_alpha         89.881(3)
_cell_oxdiff_angle_beta          96.361(2)
_cell_oxdiff_angle_gamma         90.023(3)
_cell_oxdiff_length_a            11.5810(3)
_cell_oxdiff_length_b            7.2854(4)
_cell_oxdiff_length_c            32.0249(10)
_cell_oxdiff_measurement_reflns_used 5245
_cell_oxdiff_volume              2685.38(19)
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    3.568
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.53488
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.66a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_lustre     ?
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.828
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1456
_exptl_crystal_size_max          0.185
_exptl_crystal_size_mid          0.145
_exptl_crystal_size_min          0.018
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0446
_diffrn_reflns_av_unetI/netI     0.0502
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       39
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            14724
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.259
_diffrn_reflns_theta_min         5.350
_diffrn_ambient_temperature      223.15
_diffrn_detector                 'PLATUS 200K area detector'
_diffrn_detector_area_resol_mean 5.811
_diffrn_detector_type            'HPC area detector'
_diffrn_measured_fraction_theta_full 0.999
_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     13.00  39.00   0.50    8.70    -------------------------------------   45.70 -64.00  23.00   52
  2  ω     69.00 116.00   0.50    8.70    -   45.70  64.00 160.00   94
  3  ω    125.00 186.00   0.50   34.80    -  101.80  64.00 160.00  122
  4  ω     71.00 117.00   0.50   34.80    -  101.80 -64.00  23.00   92
  5  ω      5.00 134.00   0.50    8.70    -   45.70  57.00  90.00  258
  6  ω     25.00  52.00   0.50    8.70    -   45.70  38.00   0.00   54
  7  ω      5.00 135.00   0.50    8.70    -   45.70  57.00-150.00  260
  8  ω     62.00  93.00   0.50   34.80    -  101.80  45.00-120.00   62
  9  ω     74.00 100.00   0.50   34.80    -  101.80  82.00-120.00   52
 10  ω    121.00 147.00   0.50   34.80    -  101.80  82.00-120.00   52
 11  ω     78.00 116.00   0.50   34.80    -  101.80 -61.00 150.00   76
 12  ω     72.00 147.00   0.50   34.80    -  101.80 -82.00  30.00  150
 13  ω    100.00 190.00   0.50   34.80    -  101.80  45.00-120.00  180
 14  ω     79.00 191.00   0.50   34.80    -  101.80  61.00-180.00  224
 15  ω     56.00 172.00   0.50   34.80    -  101.80  45.00 -90.00  232
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Rigaku XtaLAB PRO'
_diffrn_measurement_method       'ω scans'
_diffrn_oxdiff_digest_hkl        
;
015ad40cc29b7a23348f743ab263130ae4d1a5
;
_diffrn_radiation_monochromator  'multi-layer mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'micromax 003'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4349
_reflns_number_total             5223
_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 1.171.40.66a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.66a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.66a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_refine_diff_density_max         0.769
_refine_diff_density_min         -0.695
_refine_diff_density_rms         0.098
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.110
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     415
_refine_ls_number_reflns         5223
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0832
_refine_ls_R_factor_gt           0.0751
_refine_ls_restrained_S_all      1.110
_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)+(0.1126P)²+4.3585P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2268
_refine_ls_wR_factor_ref         0.2333
_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), N2(H2), C2(H2A), C14(H14), C8(H8), C20(H20), C18(H18), C5(H5),
 C17(H17), C6(H6)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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
Cl2 Cl 0.61833(12) 0.52974(17) 0.17659(4) 0.0640(4) Uani 1 1 d . . . . .
Cl1 Cl 0.31494(14) 1.03037(18) 0.17322(4) 0.0710(4) Uani 1 1 d . . . . .
F9 F 0.1127(2) 0.9803(4) 0.40081(9) 0.0650(8) Uani 1 1 d . . . . .
F7 F 0.1847(2) 1.0483(5) 0.46329(9) 0.0677(8) Uani 1 1 d . . . . .
F8 F 0.1979(3) 1.2380(4) 0.41337(10) 0.0699(8) Uani 1 1 d . . . . .
F2 F 0.5204(2) 1.0126(5) 0.43662(10) 0.0753(9) Uani 1 1 d . . . . .
F5 F 0.3502(3) 0.7957(5) 0.47682(9) 0.0740(8) Uani 1 1 d . . . . .
F3 F 0.4043(3) 1.1584(5) 0.47220(9) 0.0781(9) Uani 1 1 d . . . . .
F4 F 0.4151(3) 0.6858(4) 0.42227(10) 0.0752(9) Uani 1 1 d . . . . .
F1 F 0.4301(3) 1.2488(4) 0.41010(10) 0.0755(9) Uani 1 1 d . . . . .
F6 F 0.2339(3) 0.6869(4) 0.42651(10) 0.0742(8) Uani 1 1 d . . . . .
F12 F 0.6286(2) 0.4688(5) 0.44354(10) 0.0756(9) Uani 1 1 d . . . . .
F14 F 1.0015(2) 0.5287(6) 0.39696(10) 0.0837(11) Uani 1 1 d . . . . .
F16 F 0.7427(3) 0.1735(4) 0.42383(11) 0.0798(9) Uani 1 1 d . . . . .
F13 F 0.9049(3) 0.7652(5) 0.41165(10) 0.0831(10) Uani 1 1 d . . . . .
F15 F 0.9744(3) 0.5830(6) 0.46031(9) 0.0896(12) Uani 1 1 d . . . . .
F17 F 0.8561(3) 0.2804(5) 0.47390(9) 0.0851(10) Uani 1 1 d . . . . .
F18 F 0.9208(3) 0.2074(5) 0.41646(11) 0.0862(10) Uani 1 1 d . . . . .
N1 N 0.4248(3) 0.8938(5) 0.35222(11) 0.0446(8) Uani 1 1 d . . . . .
H1 H 0.483555 0.847331 0.367347 0.054 Uiso 1 1 calc R U . . .
N2 N 0.6543(3) 0.3984(5) 0.35696(11) 0.0460(8) Uani 1 1 d . . . . .
H2 H 0.608957 0.350112 0.373472 0.055 Uiso 1 1 calc R U . . .
F10 F 0.6800(3) 0.7265(5) 0.42097(15) 0.1065(13) Uani 1 1 d . . . . .
F11 F 0.7627(3) 0.6160(7) 0.47924(12) 0.1132(16) Uani 1 1 d . . . . .
C2 C 0.2532(3) 1.0303(5) 0.33438(13) 0.0408(8) Uani 1 1 d . . . . .
H2A H 0.181684 1.086402 0.335976 0.049 Uiso 1 1 calc R U . . .
C14 C 0.8078(3) 0.5397(5) 0.33462(12) 0.0393(8) Uani 1 1 d . . . . .
H14 H 0.879053 0.598147 0.334262 0.047 Uiso 1 1 calc R U . . .
C15 C 0.7254(3) 0.5025(5) 0.29896(13) 0.0403(8) Uani 1 1 d . . . . .
C4 C 0.4139(3) 0.9101(5) 0.30971(14) 0.0428(9) Uani 1 1 d . . . . .
C8 C 0.2753(4) 1.0348(5) 0.25465(13) 0.0446(9) Uani 1 1 d . . . . .
H8 H 0.205184 1.091945 0.245672 0.053 Uiso 1 1 calc R U . . .
C1 C 0.3257(3) 0.9645(5) 0.36742(13) 0.0402(8) Uani 1 1 d . . . . .
C3 C 0.3066(3) 0.9976(5) 0.29683(13) 0.0401(8) Uani 1 1 d . . . . .
C13 C 0.7624(3) 0.4733(5) 0.36939(13) 0.0417(8) Uani 1 1 d . . . . .
C16 C 0.6309(3) 0.4131(5) 0.31458(13) 0.0429(9) Uani 1 1 d . . . . .
C20 C 0.7234(3) 0.5382(5) 0.25625(13) 0.0439(9) Uani 1 1 d . . . . .
H20 H 0.785447 0.596192 0.245601 0.053 Uiso 1 1 calc R U . . .
C9 C 0.3189(3) 0.9758(5) 0.41406(13) 0.0415(9) Uani 1 1 d . . . . .
C12 C 0.2012(3) 1.0633(6) 0.42314(14) 0.0492(10) Uani 1 1 d . . . . .
C19 C 0.6267(4) 0.4849(5) 0.23018(14) 0.0469(9) Uani 1 1 d . . . . .
C21 C 0.8099(3) 0.4797(6) 0.41530(13) 0.0435(9) Uani 1 1 d . . . . .
C7 C 0.3508(4) 0.9847(6) 0.22651(14) 0.0519(10) Uani 1 1 d . . . . .
C18 C 0.5324(4) 0.3934(6) 0.24554(15) 0.0523(10) Uani 1 1 d . . . . .
H18 H 0.469357 0.356289 0.226956 0.063 Uiso 1 1 calc R U . . .
C5 C 0.4894(4) 0.8608(6) 0.28040(15) 0.0522(10) Uani 1 1 d . . . . .
H5 H 0.560150 0.804762 0.288970 0.063 Uiso 1 1 calc R U . . .
C17 C 0.5333(3) 0.3592(6) 0.28732(15) 0.0506(10) Uani 1 1 d . . . . .
H17 H 0.470693 0.301405 0.297641 0.061 Uiso 1 1 calc R U . . .
C6 C 0.4570(4) 0.8966(6) 0.23906(16) 0.0555(11) Uani 1 1 d . . . . .
H6 H 0.505357 0.862732 0.219025 0.067 Uiso 1 1 calc R U . . .
C23 C 0.8335(4) 0.2834(6) 0.43317(14) 0.0519(10) Uani 1 1 d . . . . .
C11 C 0.3295(4) 0.7847(7) 0.43571(15) 0.0535(10) Uani 1 1 d . . . . .
C10 C 0.4186(4) 1.1010(7) 0.43402(15) 0.0544(11) Uani 1 1 d . . . . .
C22 C 0.9249(4) 0.5904(8) 0.42159(15) 0.0595(12) Uani 1 1 d . . . . .
C24 C 0.7207(4) 0.5752(7) 0.44084(18) 0.0641(13) Uani 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
Cl2 C19 1.739(5) . ?
Cl1 C7 1.743(5) . ?
F9 C12 1.329(5) . ?
F7 C12 1.325(5) . ?
F8 C12 1.310(5) . ?
F2 C10 1.338(5) . ?
F5 C11 1.314(5) . ?
F3 C10 1.320(5) . ?
F4 C11 1.335(5) . ?
F1 C10 1.336(6) . ?
F6 C11 1.322(5) . ?
F12 C24 1.329(6) . ?
F14 C22 1.329(6) . ?
F16 C23 1.330(5) . ?
F13 C22 1.327(6) . ?
F15 C22 1.309(5) . ?
F17 C23 1.302(5) . ?
F18 C23 1.317(5) . ?
N1 H1 0.8600 . ?
N1 C4 1.358(5) . ?
N1 C1 1.394(5) . ?
N2 H2 0.8600 . ?
N2 C13 1.384(5) . ?
N2 C16 1.358(5) . ?
F10 C24 1.332(7) . ?
F11 C24 1.306(6) . ?
C2 H2A 0.9300 . ?
C2 C1 1.364(6) . ?
C2 C3 1.431(5) . ?
C14 H14 0.9300 . ?
C14 C15 1.431(6) . ?
C14 C13 1.371(6) . ?
C15 C16 1.412(5) . ?
C15 C20 1.390(6) . ?
C4 C3 1.418(5) . ?
C4 C5 1.398(5) . ?
C8 H8 0.9300 . ?
C8 C3 1.386(6) . ?
C8 C7 1.372(6) . ?
C1 C9 1.507(6) . ?
C13 C21 1.513(6) . ?
C16 C17 1.406(5) . ?
C20 H20 0.9300 . ?
C20 C19 1.377(6) . ?
C9 C12 1.561(5) . ?
C9 C11 1.554(6) . ?
C9 C10 1.553(5) . ?
C19 C18 1.414(6) . ?
C21 C23 1.553(6) . ?
C21 C22 1.551(6) . ?
C21 C24 1.551(6) . ?
C7 C6 1.406(7) . ?
C18 H18 0.9300 . ?
C18 C17 1.359(6) . ?
C5 H5 0.9300 . ?
C5 C6 1.361(7) . ?
C17 H17 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
C4 N1 H1 125.4 . . ?
C4 N1 C1 109.1(3) . . ?
C1 N1 H1 125.4 . . ?
C13 N2 H2 125.3 . . ?
C16 N2 H2 125.3 . . ?
C16 N2 C13 109.3(3) . . ?
C1 C2 H2A 126.1 . . ?
C1 C2 C3 107.9(3) . . ?
C3 C2 H2A 126.1 . . ?
C15 C14 H14 126.3 . . ?
C13 C14 H14 126.3 . . ?
C13 C14 C15 107.4(3) . . ?
C16 C15 C14 106.3(3) . . ?
C20 C15 C14 133.4(4) . . ?
C20 C15 C16 120.3(4) . . ?
N1 C4 C3 108.2(3) . . ?
N1 C4 C5 130.8(4) . . ?
C5 C4 C3 120.9(4) . . ?
C3 C8 H8 121.0 . . ?
C7 C8 H8 121.0 . . ?
C7 C8 C3 118.1(4) . . ?
N1 C1 C9 120.1(3) . . ?
C2 C1 N1 108.7(3) . . ?
C2 C1 C9 130.9(3) . . ?
C4 C3 C2 106.0(4) . . ?
C8 C3 C2 134.1(4) . . ?
C8 C3 C4 119.9(4) . . ?
N2 C13 C21 120.8(3) . . ?
C14 C13 N2 108.7(3) . . ?
C14 C13 C21 130.3(3) . . ?
N2 C16 C15 108.2(3) . . ?
N2 C16 C17 131.0(4) . . ?
C17 C16 C15 120.7(4) . . ?
C15 C20 H20 121.0 . . ?
C19 C20 C15 117.9(4) . . ?
C19 C20 H20 121.0 . . ?
C1 C9 C12 110.4(3) . . ?
C1 C9 C11 112.5(3) . . ?
C1 C9 C10 108.8(3) . . ?
C11 C9 C12 108.1(3) . . ?
C10 C9 C12 108.0(3) . . ?
C10 C9 C11 108.9(3) . . ?
F9 C12 C9 110.6(3) . . ?
F7 C12 F9 107.4(3) . . ?
F7 C12 C9 111.7(4) . . ?
F8 C12 F9 108.2(4) . . ?
F8 C12 F7 108.0(4) . . ?
F8 C12 C9 110.8(3) . . ?
C20 C19 Cl2 119.9(3) . . ?
C20 C19 C18 122.0(4) . . ?
C18 C19 Cl2 118.1(3) . . ?
C13 C21 C23 111.1(3) . . ?
C13 C21 C22 111.0(3) . . ?
C13 C21 C24 109.5(3) . . ?
C22 C21 C23 108.5(3) . . ?
C24 C21 C23 108.6(4) . . ?
C24 C21 C22 108.1(4) . . ?
C8 C7 Cl1 119.4(4) . . ?
C8 C7 C6 122.3(4) . . ?
C6 C7 Cl1 118.3(3) . . ?
C19 C18 H18 119.8 . . ?
C17 C18 C19 120.4(4) . . ?
C17 C18 H18 119.8 . . ?
C4 C5 H5 120.7 . . ?
C6 C5 C4 118.6(4) . . ?
C6 C5 H5 120.7 . . ?
C16 C17 H17 120.7 . . ?
C18 C17 C16 118.6(4) . . ?
C18 C17 H17 120.7 . . ?
C7 C6 H6 119.9 . . ?
C5 C6 C7 120.3(4) . . ?
C5 C6 H6 119.9 . . ?
F16 C23 C21 111.6(3) . . ?
F17 C23 F16 106.4(4) . . ?
F17 C23 F18 108.8(4) . . ?
F17 C23 C21 113.1(4) . . ?
F18 C23 F16 106.2(4) . . ?
F18 C23 C21 110.5(4) . . ?
F5 C11 F4 107.2(4) . . ?
F5 C11 F6 108.2(4) . . ?
F5 C11 C9 112.9(4) . . ?
F4 C11 C9 111.4(3) . . ?
F6 C11 F4 105.7(4) . . ?
F6 C11 C9 111.1(3) . . ?
F2 C10 C9 110.7(4) . . ?
F3 C10 F2 107.1(4) . . ?
F3 C10 F1 107.8(4) . . ?
F3 C10 C9 113.8(4) . . ?
F1 C10 F2 106.3(4) . . ?
F1 C10 C9 110.7(4) . . ?
F14 C22 C21 111.5(4) . . ?
F13 C22 F14 107.0(4) . . ?
F13 C22 C21 110.1(4) . . ?
F15 C22 F14 107.2(4) . . ?
F15 C22 F13 108.3(4) . . ?
F15 C22 C21 112.5(4) . . ?
F12 C24 F10 105.6(4) . . ?
F12 C24 C21 111.0(4) . . ?
F10 C24 C21 109.9(4) . . ?
F11 C24 F12 106.8(5) . . ?
F11 C24 F10 109.7(5) . . ?
F11 C24 C21 113.4(4) . . ?

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
Cl2 C19 C18 C17 -178.3(3) . . . . ?
Cl1 C7 C6 C5 179.0(3) . . . . ?
N1 C4 C3 C2 -0.8(4) . . . . ?
N1 C4 C3 C8 178.5(3) . . . . ?
N1 C4 C5 C6 -178.7(4) . . . . ?
N1 C1 C9 C12 178.7(3) . . . . ?
N1 C1 C9 C11 -60.4(4) . . . . ?
N1 C1 C9 C10 60.3(4) . . . . ?
N2 C13 C21 C23 66.1(5) . . . . ?
N2 C13 C21 C22 -173.1(4) . . . . ?
N2 C13 C21 C24 -53.9(5) . . . . ?
N2 C16 C17 C18 179.2(4) . . . . ?
C2 C1 C9 C12 6.3(6) . . . . ?
C2 C1 C9 C11 127.2(4) . . . . ?
C2 C1 C9 C10 -112.1(5) . . . . ?
C14 C15 C16 N2 0.4(4) . . . . ?
C14 C15 C16 C17 179.2(4) . . . . ?
C14 C15 C20 C19 -178.7(4) . . . . ?
C14 C13 C21 C23 -117.0(4) . . . . ?
C14 C13 C21 C22 3.7(6) . . . . ?
C14 C13 C21 C24 123.0(5) . . . . ?
C15 C14 C13 N2 -0.8(4) . . . . ?
C15 C14 C13 C21 -178.0(4) . . . . ?
C15 C16 C17 C18 0.6(6) . . . . ?
C15 C20 C19 Cl2 178.8(3) . . . . ?
C15 C20 C19 C18 -1.3(6) . . . . ?
C4 N1 C1 C2 -1.6(4) . . . . ?
C4 N1 C1 C9 -175.6(3) . . . . ?
C4 C5 C6 C7 1.2(6) . . . . ?
C8 C7 C6 C5 -1.2(7) . . . . ?
C1 N1 C4 C3 1.5(4) . . . . ?
C1 N1 C4 C5 179.6(4) . . . . ?
C1 C2 C3 C4 -0.2(4) . . . . ?
C1 C2 C3 C8 -179.4(4) . . . . ?
C1 C9 C12 F9 50.4(5) . . . . ?
C1 C9 C12 F7 169.9(3) . . . . ?
C1 C9 C12 F8 -69.7(4) . . . . ?
C1 C9 C11 F5 165.4(3) . . . . ?
C1 C9 C11 F4 44.7(5) . . . . ?
C1 C9 C11 F6 -72.9(4) . . . . ?
C1 C9 C10 F2 -75.5(4) . . . . ?
C1 C9 C10 F3 163.7(4) . . . . ?
C1 C9 C10 F1 42.1(5) . . . . ?
C3 C2 C1 N1 1.1(4) . . . . ?
C3 C2 C1 C9 174.2(4) . . . . ?
C3 C4 C5 C6 -0.8(6) . . . . ?
C3 C8 C7 Cl1 -179.6(3) . . . . ?
C3 C8 C7 C6 0.6(6) . . . . ?
C13 N2 C16 C15 -0.9(4) . . . . ?
C13 N2 C16 C17 -179.6(4) . . . . ?
C13 C14 C15 C16 0.3(4) . . . . ?
C13 C14 C15 C20 179.5(4) . . . . ?
C13 C21 C23 F16 -49.4(5) . . . . ?
C13 C21 C23 F17 -169.3(3) . . . . ?
C13 C21 C23 F18 68.5(4) . . . . ?
C13 C21 C22 F14 -53.0(5) . . . . ?
C13 C21 C22 F13 65.7(5) . . . . ?
C13 C21 C22 F15 -173.5(4) . . . . ?
C13 C21 C24 F12 71.2(5) . . . . ?
C13 C21 C24 F10 -45.2(5) . . . . ?
C13 C21 C24 F11 -168.5(4) . . . . ?
C16 N2 C13 C14 1.1(5) . . . . ?
C16 N2 C13 C21 178.6(3) . . . . ?
C16 C15 C20 C19 0.5(6) . . . . ?
C20 C15 C16 N2 -179.0(3) . . . . ?
C20 C15 C16 C17 -0.2(6) . . . . ?
C20 C19 C18 C17 1.8(6) . . . . ?
C12 C9 C11 F5 -72.4(4) . . . . ?
C12 C9 C11 F4 167.0(4) . . . . ?
C12 C9 C11 F6 49.3(5) . . . . ?
C12 C9 C10 F2 164.5(4) . . . . ?
C12 C9 C10 F3 43.8(5) . . . . ?
C12 C9 C10 F1 -77.8(4) . . . . ?
C19 C18 C17 C16 -1.4(6) . . . . ?
C7 C8 C3 C2 179.0(4) . . . . ?
C7 C8 C3 C4 -0.1(6) . . . . ?
C5 C4 C3 C2 -179.2(4) . . . . ?
C5 C4 C3 C8 0.2(6) . . . . ?
C23 C21 C22 F14 69.3(5) . . . . ?
C23 C21 C22 F13 -172.0(4) . . . . ?
C23 C21 C22 F15 -51.2(6) . . . . ?
C23 C21 C24 F12 -50.3(5) . . . . ?
C23 C21 C24 F10 -166.8(4) . . . . ?
C23 C21 C24 F11 70.0(5) . . . . ?
C11 C9 C12 F9 -73.1(4) . . . . ?
C11 C9 C12 F7 46.5(5) . . . . ?
C11 C9 C12 F8 166.9(4) . . . . ?
C11 C9 C10 F2 47.4(5) . . . . ?
C11 C9 C10 F3 -73.4(5) . . . . ?
C11 C9 C10 F1 165.0(4) . . . . ?
C10 C9 C12 F9 169.2(4) . . . . ?
C10 C9 C12 F7 -71.2(4) . . . . ?
C10 C9 C12 F8 49.2(5) . . . . ?
C10 C9 C11 F5 44.7(5) . . . . ?
C10 C9 C11 F4 -75.9(5) . . . . ?
C10 C9 C11 F6 166.5(4) . . . . ?
C22 C21 C23 F16 -171.6(4) . . . . ?
C22 C21 C23 F17 68.4(5) . . . . ?
C22 C21 C23 F18 -53.7(5) . . . . ?
C22 C21 C24 F12 -167.8(4) . . . . ?
C22 C21 C24 F10 75.7(5) . . . . ?
C22 C21 C24 F11 -47.5(6) . . . . ?
C24 C21 C23 F16 71.1(5) . . . . ?
C24 C21 C23 F17 -48.8(5) . . . . ?
C24 C21 C23 F18 -171.0(4) . . . . ?
C24 C21 C22 F14 -173.0(4) . . . . ?
C24 C21 C22 F13 -54.4(5) . . . . ?
C24 C21 C22 F15 66.4(6) . . . . ?

_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 1.618
_oxdiff_exptl_absorpt_empirical_full_min 0.678
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: MeOH'
