# 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. 
# 
#######################################################################

data_ly257
_database_code_depnum_ccdc_archive 'CCDC 2464370'
loop_
_audit_author_name
_audit_author_address
'Yang Li'
;University
China
;
_audit_update_record             
;
2025-06-15 deposited with the CCDC.	2026-01-14 downloaded from the CCDC.
;
_audit_creation_date             2024-12-24
_audit_creation_method           
;
Olex2 1.5-beta
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C13 H10 Cl F2 N O2'
_chemical_formula_sum            'C13 H10 Cl F2 N O2'
_chemical_formula_weight         285.67
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H O N S F'
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'
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                   6.76030(10)
_cell_length_b                   13.7808(3)
_cell_length_c                   13.7988(4)
_cell_angle_alpha                104.964(2)
_cell_angle_beta                 95.599(2)
_cell_angle_gamma                90.149(2)
_cell_volume                     1235.49(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    11687
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      73.0890
_cell_measurement_theta_min      4.0430
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.976
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.77131
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.121a (Rigaku Oxford Diffraction, 2024)
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    1.536
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             584
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0263
_diffrn_reflns_av_unetI/netI     0.0202
_diffrn_reflns_Laue_measured_fraction_full 0.968
_diffrn_reflns_Laue_measured_fraction_max 0.932
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            15477
_diffrn_reflns_point_group_measured_fraction_full 0.968
_diffrn_reflns_point_group_measured_fraction_max 0.932
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.224
_diffrn_reflns_theta_min         4.049
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            'HyPix-Arc 150'
_diffrn_measured_fraction_theta_full 0.968
_diffrn_measured_fraction_theta_max 0.932
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     90.00 116.00   0.50    0.05    --   75.66  22.00  44.36   52
  2  ω     55.00  96.00   0.50    0.05    --   62.19  15.00 -30.00   82
  3  ω     63.00  88.00   0.50    0.05    --   62.19  15.00 -60.00   50
  4  ω     69.00 102.00   0.50    0.05    --   62.19  15.00-120.00   66
  5  ω     62.00  91.00   0.50    0.05    --   62.19  15.00-180.00   58
  6  ω     73.00 101.00   0.50    0.05    --   62.19  15.00-150.00   56
  7  ω     64.00 111.00   0.50    0.05    --   71.25  15.00-120.00   94
  8  ω     72.00 111.00   0.50    0.05    --   74.35  15.00 -90.00   78
  9  ω     80.00 107.00   0.50    0.05    --   71.25  15.00   0.00   54
 10  ω     59.00  86.00   0.50    0.05    --   62.19  15.00  30.00   54
 11  ω     72.00 103.00   0.50    0.05    --   62.19  15.00  90.00   62
 12  ω     72.00  99.00   0.50    0.05    --   74.35  15.00 150.00   54
 13  ω     76.00 107.00   0.50    0.05    --   71.25  15.00  90.00   62
 14  ω     82.00 112.00   0.50    0.05    --   74.35  15.00  30.00   60
 15  ω     77.00 112.00   0.50    0.05    --   74.35  15.00 -30.00   70
 16  ω     55.00  85.00   0.50    0.05    --   62.19  15.00 150.00   60
 17  ω     74.00 103.00   0.50    0.05    --   74.35  15.00 120.00   58
 18  ω     80.00 107.00   0.50    0.05    --   74.35  15.00 -60.00   54
 19  ω     78.00 107.00   0.50    0.05    --   74.35  15.00-150.00   58
 20  ω     71.00 109.00   0.50    0.05    --   74.35  15.00-180.00   76
 21  ω     43.00  83.00   0.50    0.05    --   74.35-125.00-150.00   80
 22  ω     27.00  75.00   0.50    0.05    --   62.19-125.00-180.00   96
 23  ω     44.00  76.00   0.50    0.05    --   62.19-125.00-120.00   64
 24  ω     26.00  78.00   0.50    0.05    --   62.19-125.00 -90.00  104
 25  ω     30.00  55.00   0.50    0.05    --   62.19-125.00 -30.00   50
 26  ω     28.00  54.00   0.50    0.05    --   62.19-125.00   0.00   52
 27  ω     29.00  77.00   0.50    0.05    --   62.19-125.00  30.00   96
 28  ω     34.00  76.00   0.50    0.05    --   62.19-125.00  60.00   84
 29  ω     28.00  70.00   0.50    0.05    --   62.19-125.00 120.00   84
 30  ω     44.00  70.00   0.50    0.05    --   62.19-125.00 150.00   52
 31  ω     51.00  87.00   0.50    0.05    --   71.25-125.00 120.00   72
 32  ω     57.00  90.00   0.50    0.05    --   74.35-125.00  60.00   66
 33  ω     59.00  86.00   0.50    0.05    --   71.25-125.00  30.00   54
 34  ω     44.00  89.00   0.50    0.05    --   74.35-125.00   0.00   90
 35  ω     48.00  83.00   0.50    0.05    --   71.25-125.00 -60.00   70
 36  ω     59.00  85.00   0.50    0.05    --   71.25-125.00-120.00   52
 37  ω     43.00  90.00   0.50    0.05    --   74.35-125.00-180.00   94
 38  ω     54.00  88.00   0.50    0.05    --   74.35-125.00-120.00   68
 39  ω     65.00  90.00   0.50    0.05    --   74.35-125.00 -60.00   50
 40  ω     51.00  90.00   0.50    0.05    --   74.35-125.00 -30.00   78
 41  ω     38.00  63.00   0.50    0.05    --   74.35-125.00  30.00   50
 42  ω     42.00  89.00   0.50    0.05    --   74.35-125.00  90.00   94
 43  ω     45.00  88.00   0.50    0.05    --   74.35-125.00 150.00   86
 44  ω     65.00  90.00   0.50    0.05    --   74.35-125.00 120.00   50
 45  ω     39.00  89.00   0.50    0.05    --   74.35-125.00 -90.00  100
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom system, HyPix-Arc 150'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0228472000
_diffrn_orient_matrix_UB_12      0.0475488000
_diffrn_orient_matrix_UB_13      -0.0898564000
_diffrn_orient_matrix_UB_21      0.1053269000
_diffrn_orient_matrix_UB_22      -0.0895680000
_diffrn_orient_matrix_UB_23      -0.0639176000
_diffrn_orient_matrix_UB_31      -0.2021336000
_diffrn_orient_matrix_UB_32      -0.0558373000
_diffrn_orient_matrix_UB_33      -0.0365346000
_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                4327
_reflns_number_total             4607
_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 1.171.43.121a (Rigaku OD, 2024)'
_computing_data_collection       
'CrysAlisPro system (CCD 43.121a 64-bit (release 24-04-2024))'
_computing_data_reduction        'CrysAlisPro 1.171.43.121a (Rigaku OD, 2024)'
_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 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_refine_diff_density_max         0.772
_refine_diff_density_min         -0.527
_refine_diff_density_rms         0.082
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     353
_refine_ls_number_reflns         4607
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0531
_refine_ls_R_factor_gt           0.0514
_refine_ls_restrained_S_all      1.056
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0765P)²+2.6052P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1503
_refine_ls_wR_factor_ref         0.1514
_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. Restrained distances
 C12-H12A
 0.985 with sigma of 0.02
3.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C5(H5), C6(H6), C7(H7), C11(H11), C14(H14), C16(H16), C19(H19),
 C20(H20), C24(H24)
3.b X=CH2 refined with riding coordinates:
 C25(H25A,H25B)
3.c Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C38(H38A,H38B,H38C)
;
_atom_sites_solution_hydrogens   mixed
_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
Cl1 Cl 0.68268(11) 1.44432(5) 0.15359(5) 0.02630(19) Uani 1 1 d . . . . .
F1 F 0.5460(3) 0.77237(13) 0.30074(14) 0.0332(4) Uani 1 1 d . . . . .
F2 F 0.8661(3) 0.77046(13) 0.29586(14) 0.0333(4) Uani 1 1 d . . . . .
O1 O 0.7345(3) 0.94527(15) 0.41503(15) 0.0283(5) Uani 1 1 d . . . . .
O2 O 0.6936(3) 0.88985(14) 0.24364(14) 0.0201(4) Uani 1 1 d . . . . .
N1 N 0.7276(3) 1.14981(16) 0.39255(17) 0.0185(5) Uani 1 1 d . . . . .
C1 C 0.7186(4) 1.2297(2) 0.3496(2) 0.0175(5) Uani 1 1 d . . . . .
C2 C 0.6960(4) 1.1915(2) 0.2439(2) 0.0175(5) Uani 1 1 d . . . . .
C3 C 0.6828(4) 1.2581(2) 0.1814(2) 0.0189(5) Uani 1 1 d . . . . .
H3 H 0.666826 1.234090 0.110007 0.023 Uiso 1 1 calc R U . . .
C4 C 0.6941(4) 1.3592(2) 0.2281(2) 0.0190(5) Uani 1 1 d . . . . .
C5 C 0.7168(4) 1.3975(2) 0.3335(2) 0.0202(6) Uani 1 1 d . . . . .
H5 H 0.723951 1.468097 0.362151 0.024 Uiso 1 1 calc R U . . .
C6 C 0.7289(4) 1.3335(2) 0.3957(2) 0.0196(5) Uani 1 1 d . . . . .
H6 H 0.743684 1.358554 0.466957 0.024 Uiso 1 1 calc R U . . .
C7 C 0.6907(4) 1.0854(2) 0.2231(2) 0.0177(5) Uani 1 1 d . . . . .
H7 H 0.676758 1.039147 0.158322 0.021 Uiso 1 1 calc R U . . .
C8 C 0.7097(4) 1.0622(2) 0.3144(2) 0.0176(5) Uani 1 1 d . . . . .
C9 C 0.7151(4) 0.9636(2) 0.3344(2) 0.0197(6) Uani 1 1 d . . . . .
C10 C 0.6932(4) 0.7902(2) 0.2460(2) 0.0233(6) Uani 1 1 d . . . . .
C11 C 0.6646(5) 0.7217(2) 0.1428(2) 0.0282(6) Uani 1 1 d . . . . .
H11 H 0.661461 0.651427 0.136837 0.034 Uiso 1 1 calc R U . . .
C12 C 0.6436(5) 0.7510(2) 0.0594(2) 0.0297(7) Uani 1 1 d D . . . .
H12A H 0.627(5) 0.8250(15) 0.062(3) 0.031(9) Uiso 1 1 d D . . . .
H12B H 0.633(5) 0.701(3) -0.007(3) 0.034(10) Uiso 1 1 d . . . . .
C13 C 0.7519(5) 1.1577(2) 0.5006(2) 0.0251(6) Uani 1 1 d . . . . .
H13A H 0.875166 1.125822 0.517659 0.038 Uiso 1 1 calc R U . . .
H13B H 0.638703 1.123917 0.518764 0.038 Uiso 1 1 calc R U . . .
H13C H 0.757989 1.228728 0.538024 0.038 Uiso 1 1 calc R U . . .
Cl2 Cl 0.14560(11) 0.84739(5) 0.07201(6) 0.0298(2) Uani 1 1 d . . . . .
F3 F 0.0563(3) 1.59457(13) 0.34155(13) 0.0284(4) Uani 1 1 d . . . . .
F4 F 0.3776(3) 1.59482(13) 0.34401(13) 0.0283(4) Uani 1 1 d . . . . .
O3 O 0.2337(3) 1.45571(14) 0.43198(14) 0.0234(4) Uani 1 1 d . . . . .
O4 O 0.2018(3) 1.45279(14) 0.26478(14) 0.0199(4) Uani 1 1 d . . . . .
N2 N 0.2230(3) 1.23688(17) 0.37008(17) 0.0181(5) Uani 1 1 d . . . . .
C14 C 0.1967(4) 0.9609(2) 0.2651(2) 0.0217(6) Uani 1 1 d . . . . .
H14 H 0.199465 0.898294 0.282136 0.026 Uiso 1 1 calc R U . . .
C15 C 0.1729(4) 0.9625(2) 0.1633(2) 0.0214(6) Uani 1 1 d . . . . .
C16 C 0.1667(4) 1.0500(2) 0.1332(2) 0.0209(6) Uani 1 1 d . . . . .
H16 H 0.150539 1.049079 0.063772 0.025 Uiso 1 1 calc R U . . .
C17 C 0.1852(4) 1.1411(2) 0.2088(2) 0.0181(5) Uani 1 1 d . . . . .
C18 C 0.2095(4) 1.1397(2) 0.3116(2) 0.0183(5) Uani 1 1 d . . . . .
C19 C 0.2162(4) 1.0492(2) 0.3407(2) 0.0208(6) Uani 1 1 d . . . . .
H19 H 0.233381 1.048788 0.409732 0.025 Uiso 1 1 calc R U . . .
C20 C 0.1853(4) 1.2436(2) 0.2072(2) 0.0182(5) Uani 1 1 d . . . . .
H20 H 0.171919 1.268882 0.149111 0.022 Uiso 1 1 calc R U . . .
C21 C 0.2085(4) 1.2994(2) 0.3060(2) 0.0181(5) Uani 1 1 d . . . . .
C22 C 0.2165(4) 1.4088(2) 0.3454(2) 0.0192(5) Uani 1 1 d . . . . .
C23 C 0.2071(4) 1.5561(2) 0.2853(2) 0.0213(6) Uani 1 1 d . . . . .
C24 C 0.1917(4) 1.5910(2) 0.1911(2) 0.0257(6) Uani 1 1 d . . . . .
H24 H 0.188111 1.661428 0.198220 0.031 Uiso 1 1 calc R U . . .
C25 C 0.1829(5) 1.5325(3) 0.1000(2) 0.0313(7) Uani 1 1 d . . . . .
H25A H 0.186065 1.461656 0.089817 0.038 Uiso 1 1 calc R U . . .
H25B H 0.173195 1.560582 0.043751 0.038 Uiso 1 1 calc R U . . .
C38 C 0.2487(4) 1.2665(2) 0.4803(2) 0.0226(6) Uani 1 1 d . . . . .
H38A H 0.134406 1.305032 0.505565 0.034 Uiso 1 1 calc R U . . .
H38B H 0.370604 1.307975 0.503536 0.034 Uiso 1 1 calc R U . . .
H38C H 0.258329 1.206243 0.505553 0.034 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
Cl1 C4 1.745(3) . ?
F1 C10 1.365(3) . ?
F2 C10 1.362(3) . ?
O1 C9 1.199(3) . ?
O2 C9 1.388(3) . ?
O2 C10 1.382(3) . ?
N1 C1 1.377(3) . ?
N1 C8 1.392(3) . ?
N1 C13 1.460(3) . ?
C1 C2 1.411(4) . ?
C1 C6 1.406(4) . ?
C2 C3 1.410(4) . ?
C2 C7 1.414(4) . ?
C3 H3 0.9500 . ?
C3 C4 1.374(4) . ?
C4 C5 1.407(4) . ?
C5 H5 0.9500 . ?
C5 C6 1.377(4) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C7 C8 1.372(4) . ?
C8 C9 1.455(4) . ?
C10 C11 1.486(4) . ?
C11 H11 0.9500 . ?
C11 C12 1.310(5) . ?
C12 H12A 1.019(18) . ?
C12 H12B 0.99(4) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
Cl2 C15 1.749(3) . ?
F3 C23 1.366(3) . ?
F4 C23 1.364(3) . ?
O3 C22 1.197(3) . ?
O4 C22 1.393(3) . ?
O4 C23 1.377(3) . ?
N2 C18 1.371(3) . ?
N2 C21 1.383(3) . ?
N2 C38 1.461(3) . ?
C14 H14 0.9500 . ?
C14 C15 1.405(4) . ?
C14 C19 1.379(4) . ?
C15 C16 1.372(4) . ?
C16 H16 0.9500 . ?
C16 C17 1.407(4) . ?
C17 C18 1.417(4) . ?
C17 C20 1.418(4) . ?
C18 C19 1.405(4) . ?
C19 H19 0.9500 . ?
C20 H20 0.9500 . ?
C20 C21 1.374(4) . ?
C21 C22 1.463(4) . ?
C23 C24 1.493(4) . ?
C24 H24 0.9500 . ?
C24 C25 1.303(4) . ?
C25 H25A 0.9500 . ?
C25 H25B 0.9500 . ?
C38 H38A 0.9800 . ?
C38 H38B 0.9800 . ?
C38 H38C 0.9800 . ?

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 O2 C9 118.6(2) . . ?
C1 N1 C8 107.4(2) . . ?
C1 N1 C13 125.3(2) . . ?
C8 N1 C13 127.2(2) . . ?
N1 C1 C2 108.3(2) . . ?
N1 C1 C6 129.9(2) . . ?
C6 C1 C2 121.8(2) . . ?
C1 C2 C7 107.3(2) . . ?
C3 C2 C1 119.9(2) . . ?
C3 C2 C7 132.8(2) . . ?
C2 C3 H3 121.4 . . ?
C4 C3 C2 117.2(2) . . ?
C4 C3 H3 121.4 . . ?
C3 C4 Cl1 118.7(2) . . ?
C3 C4 C5 123.0(2) . . ?
C5 C4 Cl1 118.3(2) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 C4 120.5(2) . . ?
C6 C5 H5 119.7 . . ?
C1 C6 H6 121.2 . . ?
C5 C6 C1 117.5(2) . . ?
C5 C6 H6 121.2 . . ?
C2 C7 H7 126.6 . . ?
C8 C7 C2 106.8(2) . . ?
C8 C7 H7 126.6 . . ?
N1 C8 C9 121.4(2) . . ?
C7 C8 N1 110.1(2) . . ?
C7 C8 C9 128.6(2) . . ?
O1 C9 O2 123.3(2) . . ?
O1 C9 C8 127.3(3) . . ?
O2 C9 C8 109.4(2) . . ?
F1 C10 O2 109.7(2) . . ?
F1 C10 C11 109.7(2) . . ?
F2 C10 F1 105.6(2) . . ?
F2 C10 O2 109.9(2) . . ?
F2 C10 C11 110.3(2) . . ?
O2 C10 C11 111.5(2) . . ?
C10 C11 H11 117.6 . . ?
C12 C11 C10 124.8(3) . . ?
C12 C11 H11 117.6 . . ?
C11 C12 H12A 121(2) . . ?
C11 C12 H12B 120(2) . . ?
H12A C12 H12B 119(3) . . ?
N1 C13 H13A 109.5 . . ?
N1 C13 H13B 109.5 . . ?
N1 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C23 O4 C22 118.5(2) . . ?
C18 N2 C21 107.6(2) . . ?
C18 N2 C38 125.0(2) . . ?
C21 N2 C38 127.4(2) . . ?
C15 C14 H14 119.7 . . ?
C19 C14 H14 119.7 . . ?
C19 C14 C15 120.6(3) . . ?
C14 C15 Cl2 117.9(2) . . ?
C16 C15 Cl2 119.2(2) . . ?
C16 C15 C14 122.9(3) . . ?
C15 C16 H16 121.2 . . ?
C15 C16 C17 117.6(3) . . ?
C17 C16 H16 121.2 . . ?
C16 C17 C18 119.7(2) . . ?
C16 C17 C20 133.7(3) . . ?
C18 C17 C20 106.7(2) . . ?
N2 C18 C17 108.6(2) . . ?
N2 C18 C19 129.6(3) . . ?
C19 C18 C17 121.7(3) . . ?
C14 C19 C18 117.5(3) . . ?
C14 C19 H19 121.3 . . ?
C18 C19 H19 121.3 . . ?
C17 C20 H20 126.6 . . ?
C21 C20 C17 106.8(2) . . ?
C21 C20 H20 126.6 . . ?
N2 C21 C22 121.1(2) . . ?
C20 C21 N2 110.3(2) . . ?
C20 C21 C22 128.6(2) . . ?
O3 C22 O4 123.7(2) . . ?
O3 C22 C21 127.3(2) . . ?
O4 C22 C21 109.0(2) . . ?
F3 C23 O4 110.0(2) . . ?
F3 C23 C24 109.6(2) . . ?
F4 C23 F3 105.2(2) . . ?
F4 C23 O4 110.4(2) . . ?
F4 C23 C24 109.6(2) . . ?
O4 C23 C24 111.8(2) . . ?
C23 C24 H24 117.5 . . ?
C25 C24 C23 125.0(3) . . ?
C25 C24 H24 117.5 . . ?
C24 C25 H25A 120.0 . . ?
C24 C25 H25B 120.0 . . ?
H25A C25 H25B 120.0 . . ?
N2 C38 H38A 109.5 . . ?
N2 C38 H38B 109.5 . . ?
N2 C38 H38C 109.5 . . ?
H38A C38 H38B 109.5 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 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
Cl1 C4 C5 C6 -179.2(2) . . . . ?
F1 C10 C11 C12 122.1(3) . . . . ?
F2 C10 C11 C12 -122.0(3) . . . . ?
O2 C10 C11 C12 0.4(4) . . . . ?
N1 C1 C2 C3 -180.0(2) . . . . ?
N1 C1 C2 C7 0.2(3) . . . . ?
N1 C1 C6 C5 179.6(3) . . . . ?
N1 C8 C9 O1 -0.1(4) . . . . ?
N1 C8 C9 O2 179.8(2) . . . . ?
C1 N1 C8 C7 0.3(3) . . . . ?
C1 N1 C8 C9 179.5(2) . . . . ?
C1 C2 C3 C4 0.4(4) . . . . ?
C1 C2 C7 C8 0.0(3) . . . . ?
C2 C1 C6 C5 -0.2(4) . . . . ?
C2 C3 C4 Cl1 178.91(19) . . . . ?
C2 C3 C4 C5 -0.3(4) . . . . ?
C2 C7 C8 N1 -0.2(3) . . . . ?
C2 C7 C8 C9 -179.3(3) . . . . ?
C3 C2 C7 C8 -179.8(3) . . . . ?
C3 C4 C5 C6 -0.1(4) . . . . ?
C4 C5 C6 C1 0.3(4) . . . . ?
C6 C1 C2 C3 -0.1(4) . . . . ?
C6 C1 C2 C7 -179.9(2) . . . . ?
C7 C2 C3 C4 -179.9(3) . . . . ?
C7 C8 C9 O1 178.9(3) . . . . ?
C7 C8 C9 O2 -1.2(4) . . . . ?
C8 N1 C1 C2 -0.3(3) . . . . ?
C8 N1 C1 C6 179.8(3) . . . . ?
C9 O2 C10 F1 57.1(3) . . . . ?
C9 O2 C10 F2 -58.5(3) . . . . ?
C9 O2 C10 C11 178.8(2) . . . . ?
C10 O2 C9 O1 0.4(4) . . . . ?
C10 O2 C9 C8 -179.5(2) . . . . ?
C13 N1 C1 C2 179.6(2) . . . . ?
C13 N1 C1 C6 -0.3(5) . . . . ?
C13 N1 C8 C7 -179.6(3) . . . . ?
C13 N1 C8 C9 -0.4(4) . . . . ?
Cl2 C15 C16 C17 178.8(2) . . . . ?
F3 C23 C24 C25 -125.0(3) . . . . ?
F4 C23 C24 C25 120.0(3) . . . . ?
O4 C23 C24 C25 -2.8(4) . . . . ?
N2 C18 C19 C14 179.4(3) . . . . ?
N2 C21 C22 O3 -0.7(4) . . . . ?
N2 C21 C22 O4 179.0(2) . . . . ?
C14 C15 C16 C17 0.0(4) . . . . ?
C15 C14 C19 C18 0.5(4) . . . . ?
C15 C16 C17 C18 0.1(4) . . . . ?
C15 C16 C17 C20 -179.8(3) . . . . ?
C16 C17 C18 N2 -179.7(2) . . . . ?
C16 C17 C18 C19 0.1(4) . . . . ?
C16 C17 C20 C21 179.8(3) . . . . ?
C17 C18 C19 C14 -0.4(4) . . . . ?
C17 C20 C21 N2 0.0(3) . . . . ?
C17 C20 C21 C22 -179.5(3) . . . . ?
C18 N2 C21 C20 0.2(3) . . . . ?
C18 N2 C21 C22 179.7(2) . . . . ?
C18 C17 C20 C21 -0.1(3) . . . . ?
C19 C14 C15 Cl2 -179.1(2) . . . . ?
C19 C14 C15 C16 -0.3(4) . . . . ?
C20 C17 C18 N2 0.2(3) . . . . ?
C20 C17 C18 C19 -179.9(2) . . . . ?
C20 C21 C22 O3 178.7(3) . . . . ?
C20 C21 C22 O4 -1.6(4) . . . . ?
C21 N2 C18 C17 -0.2(3) . . . . ?
C21 N2 C18 C19 180.0(3) . . . . ?
C22 O4 C23 F3 -58.5(3) . . . . ?
C22 O4 C23 F4 57.1(3) . . . . ?
C22 O4 C23 C24 179.4(2) . . . . ?
C23 O4 C22 O3 0.0(4) . . . . ?
C23 O4 C22 C21 -179.8(2) . . . . ?
C38 N2 C18 C17 179.9(2) . . . . ?
C38 N2 C18 C19 0.1(5) . . . . ?
C38 N2 C21 C20 -180.0(2) . . . . ?
C38 N2 C21 C22 -0.5(4) . . . . ?

_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 1.385
_oxdiff_exptl_absorpt_empirical_full_min 0.532
