# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2022

####################################################################### 
# 
# 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_4aj
_database_code_depnum_ccdc_archive 'CCDC 2130549'
loop_
_audit_author_name
_audit_author_address
'Xinying Zhang'
;Henan Normal University
China
;
_audit_update_record             
;
2021-12-22 deposited with the CCDC.	2022-01-25 downloaded from the CCDC.
;
_audit_creation_date             2021-09-08
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H22 F3 N3 O4'
_chemical_formula_sum            'C23 H22 F3 N3 O4'
_chemical_formula_weight         461.43
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C1 H1 O1 F1 N1'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 '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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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                   8.8292(5)
_cell_length_b                   9.7212(7)
_cell_length_c                   24.9451(14)
_cell_angle_alpha                90
_cell_angle_beta                 92.046(6)
_cell_angle_gamma                90
_cell_volume                     2139.7(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4985
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.7720
_cell_measurement_theta_min      3.8520
_shelx_estimated_absorpt_T_max   0.988
_shelx_estimated_absorpt_T_min   0.977
_exptl_absorpt_coefficient_mu    0.116
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.26776
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.53 (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 yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.432
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             960
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0446
_diffrn_reflns_av_unetI/netI     0.0441
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.886
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            16247
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.886
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.119
_diffrn_reflns_theta_min         3.269
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0521
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.886
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     15.00  40.00   1.00    9.12    --   16.29-131.00  88.00   25
  2  ω     19.00  44.00   1.00    9.12    --   16.29-139.00 -86.00   25
  3  ω    -74.00 -49.00   1.00    9.12    --  -16.91 131.00 159.00   25
  4  ω    -78.00 -43.00   1.00    9.12    --  -16.91 139.00 -25.00   35
  5  ω      7.00  33.00   1.00    9.12    --   16.29 -57.00 -30.00   26
  6  ω    -55.00  -9.00   1.00    9.12    --   16.29 -19.00  30.00   46
  7  ω     -5.00  38.00   1.00    9.12    --   16.29 -19.00  30.00   43
  8  ω    -32.00  41.00   1.00    9.12    --  -16.91  57.00 120.00   73
  9  ω    -84.00   7.00   1.00    9.12    --  -16.91 -77.00-120.00   91
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0603443000
_diffrn_orient_matrix_UB_12      -0.0417957000
_diffrn_orient_matrix_UB_13      0.0101716000
_diffrn_orient_matrix_UB_21      0.0414881000
_diffrn_orient_matrix_UB_22      0.0597406000
_diffrn_orient_matrix_UB_23      0.0076148000
_diffrn_orient_matrix_UB_31      -0.0331941000
_diffrn_orient_matrix_UB_32      -0.0012101000
_diffrn_orient_matrix_UB_33      0.0254726000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3713
_reflns_number_total             5091
_reflns_odcompleteness_completeness 99.51
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_refine_diff_density_max         0.225
_refine_diff_density_min         -0.258
_refine_diff_density_rms         0.046
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     300
_refine_ls_number_reflns         5091
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0778
_refine_ls_R_factor_gt           0.0549
_refine_ls_restrained_S_all      1.054
_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)+(0.0579P)²+0.5272P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1272
_refine_ls_wR_factor_ref         0.1431
_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:
 C17(H17)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C10(H10A,H10B), C20(H20A,H20B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C11(H11), C12(H12), C14(H14), C15(H15)
2.d Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C), C23(H23A,H23B,H23C)
;
_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
F1 F -0.28678(15) 0.6480(2) 0.41886(7) 0.0909(6) Uani 1 1 d . . . . .
F2 F -0.0889(2) 0.5521(2) 0.45345(6) 0.0969(6) Uani 1 1 d . . . . .
F3 F -0.0839(2) 0.76090(19) 0.43121(8) 0.1001(6) Uani 1 1 d . . . . .
O1 O 0.8689(2) -0.0174(2) 0.56988(8) 0.0824(6) Uani 1 1 d . . . . .
O2 O 0.6678(2) 0.0369(2) 0.61097(7) 0.0755(5) Uani 1 1 d . . . . .
O3 O 0.06881(14) 0.59012(14) 0.36212(6) 0.0433(3) Uani 1 1 d . . . . .
O4 O 0.05833(15) 0.36070(15) 0.36676(7) 0.0574(4) Uani 1 1 d . . . . .
N1 N 0.53095(15) 0.32389(16) 0.38896(5) 0.0307(3) Uani 1 1 d . . . . .
N2 N 0.63340(15) 0.34979(15) 0.34841(5) 0.0315(3) Uani 1 1 d . . . . .
N3 N 0.7473(2) 0.04235(18) 0.57179(7) 0.0511(5) Uani 1 1 d . . . . .
C1 C 0.5718(2) 0.4655(2) 0.21393(8) 0.0422(5) Uani 1 1 d . . . . .
H1 H 0.472388 0.495099 0.217202 0.051 Uiso 1 1 calc R U . . .
C2 C 0.6510(3) 0.5032(2) 0.16942(8) 0.0517(5) Uani 1 1 d . . . . .
H2 H 0.604618 0.557332 0.142843 0.062 Uiso 1 1 calc R U . . .
C3 C 0.7976(3) 0.4607(2) 0.16447(8) 0.0508(5) Uani 1 1 d . . . . .
H3 H 0.851270 0.486777 0.134705 0.061 Uiso 1 1 calc R U . . .
C4 C 0.8658(2) 0.3794(2) 0.20360(8) 0.0492(5) Uani 1 1 d . . . . .
H4 H 0.965205 0.350143 0.199956 0.059 Uiso 1 1 calc R U . . .
C5 C 0.7878(2) 0.3409(2) 0.24813(7) 0.0407(4) Uani 1 1 d . . . . .
H5 H 0.834857 0.286159 0.274379 0.049 Uiso 1 1 calc R U . . .
C6 C 0.6391(2) 0.38376(18) 0.25385(7) 0.0325(4) Uani 1 1 d . . . . .
C7 C 0.55920(19) 0.35000(17) 0.30312(6) 0.0299(4) Uani 1 1 d . . . . .
C8 C 0.39813(19) 0.30868(18) 0.30854(6) 0.0302(4) Uani 1 1 d . . . . .
C9 C 0.3494(2) 0.1746(2) 0.28194(8) 0.0437(5) Uani 1 1 d . . . . .
H9A H 0.418176 0.132434 0.257325 0.052 Uiso 1 1 calc R U . . .
H9B H 0.291465 0.110343 0.302771 0.052 Uiso 1 1 calc R U . . .
C10 C 0.2748(2) 0.3057(2) 0.26522(7) 0.0423(5) Uani 1 1 d . . . . .
H10A H 0.171462 0.320770 0.275799 0.051 Uiso 1 1 calc R U . . .
H10B H 0.298110 0.342850 0.230376 0.051 Uiso 1 1 calc R U . . .
C11 C 0.48597(19) 0.21734(18) 0.47457(7) 0.0319(4) Uani 1 1 d . . . . .
H11 H 0.383047 0.236805 0.470637 0.038 Uiso 1 1 calc R U . . .
C12 C 0.5409(2) 0.15120(18) 0.51990(7) 0.0365(4) Uani 1 1 d . . . . .
H12 H 0.475932 0.128777 0.547111 0.044 Uiso 1 1 calc R U . . .
C13 C 0.6924(2) 0.11826(18) 0.52492(7) 0.0361(4) Uani 1 1 d . . . . .
C14 C 0.7916(2) 0.15299(19) 0.48556(7) 0.0372(4) Uani 1 1 d . . . . .
H14 H 0.893328 0.128628 0.489168 0.045 Uiso 1 1 calc R U . . .
C15 C 0.73891(19) 0.22383(18) 0.44102(7) 0.0325(4) Uani 1 1 d . . . . .
H15 H 0.806247 0.250902 0.415205 0.039 Uiso 1 1 calc R U . . .
C16 C 0.58427(18) 0.25573(16) 0.43412(6) 0.0275(3) Uani 1 1 d . . . . .
C17 C 0.37240(17) 0.33226(17) 0.36783(6) 0.0271(3) Uani 1 1 d . . . . .
H17 H 0.311774 0.257444 0.382346 0.033 Uiso 1 1 calc R U . . .
C18 C 0.30036(18) 0.47413(17) 0.38054(7) 0.0295(4) Uani 1 1 d . . . . .
C19 C 0.1311(2) 0.46365(19) 0.36824(7) 0.0352(4) Uani 1 1 d . . . . .
C20 C -0.0928(2) 0.5989(2) 0.36206(8) 0.0443(5) Uani 1 1 d . . . . .
H20A H -0.137335 0.510616 0.352571 0.053 Uiso 1 1 calc R U . . .
H20B H -0.128659 0.666467 0.335940 0.053 Uiso 1 1 calc R U . . .
C21 C -0.1373(2) 0.6397(3) 0.41627(9) 0.0537(6) Uani 1 1 d . . . . .
C22 C 0.3138(2) 0.5056(2) 0.44100(8) 0.0435(5) Uani 1 1 d . . . . .
H22A H 0.261476 0.436003 0.460440 0.065 Uiso 1 1 calc R U . . .
H22B H 0.269462 0.593762 0.447822 0.065 Uiso 1 1 calc R U . . .
H22C H 0.418723 0.506577 0.452461 0.065 Uiso 1 1 calc R U . . .
C23 C 0.3730(2) 0.59221(18) 0.35002(8) 0.0390(4) Uani 1 1 d . . . . .
H23A H 0.480013 0.594085 0.358335 0.058 Uiso 1 1 calc R U . . .
H23B H 0.328622 0.677860 0.360423 0.058 Uiso 1 1 calc R U . . .
H23C H 0.356025 0.578736 0.312155 0.058 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
F1 C21 1.326(2) . ?
F2 C21 1.319(3) . ?
F3 C21 1.318(3) . ?
O1 N3 1.224(2) . ?
O2 N3 1.225(2) . ?
O3 C19 1.353(2) . ?
O3 C20 1.430(2) . ?
O4 C19 1.189(2) . ?
N1 N2 1.4034(18) . ?
N1 C16 1.376(2) . ?
N1 C17 1.480(2) . ?
N2 C7 1.286(2) . ?
N3 C13 1.451(2) . ?
C1 H1 0.9300 . ?
C1 C2 1.383(3) . ?
C1 C6 1.391(2) . ?
C2 H2 0.9300 . ?
C2 C3 1.369(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.378(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.379(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.390(2) . ?
C6 C7 1.475(2) . ?
C7 C8 1.489(2) . ?
C8 C9 1.518(2) . ?
C8 C10 1.507(2) . ?
C8 C17 1.522(2) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 C10 1.487(3) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 H11 0.9300 . ?
C11 C12 1.374(2) . ?
C11 C16 1.405(2) . ?
C12 H12 0.9300 . ?
C12 C13 1.376(3) . ?
C13 C14 1.381(3) . ?
C14 H14 0.9300 . ?
C14 C15 1.374(2) . ?
C15 H15 0.9300 . ?
C15 C16 1.405(2) . ?
C17 H17 0.9800 . ?
C17 C18 1.556(2) . ?
C18 C19 1.518(2) . ?
C18 C22 1.539(2) . ?
C18 C23 1.531(2) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C20 C21 1.476(3) . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 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
C19 O3 C20 117.15(15) . . ?
N2 N1 C17 111.05(12) . . ?
C16 N1 N2 117.78(13) . . ?
C16 N1 C17 127.57(13) . . ?
C7 N2 N1 108.20(13) . . ?
O1 N3 O2 122.64(18) . . ?
O1 N3 C13 118.59(18) . . ?
O2 N3 C13 118.73(19) . . ?
C2 C1 H1 119.6 . . ?
C2 C1 C6 120.75(19) . . ?
C6 C1 H1 119.6 . . ?
C1 C2 H2 120.0 . . ?
C3 C2 C1 120.0(2) . . ?
C3 C2 H2 120.0 . . ?
C2 C3 H3 120.0 . . ?
C2 C3 C4 119.99(18) . . ?
C4 C3 H3 120.0 . . ?
C3 C4 H4 119.7 . . ?
C3 C4 C5 120.54(19) . . ?
C5 C4 H4 119.7 . . ?
C4 C5 H5 119.9 . . ?
C4 C5 C6 120.14(18) . . ?
C6 C5 H5 119.9 . . ?
C1 C6 C7 121.27(16) . . ?
C5 C6 C1 118.60(16) . . ?
C5 C6 C7 120.02(16) . . ?
N2 C7 C6 119.26(15) . . ?
N2 C7 C8 112.21(14) . . ?
C6 C7 C8 128.49(15) . . ?
C7 C8 C9 116.67(15) . . ?
C7 C8 C10 127.46(15) . . ?
C7 C8 C17 102.95(13) . . ?
C9 C8 C17 120.30(15) . . ?
C10 C8 C9 58.90(13) . . ?
C10 C8 C17 124.82(15) . . ?
C8 C9 H9A 117.8 . . ?
C8 C9 H9B 117.8 . . ?
H9A C9 H9B 114.9 . . ?
C10 C9 C8 60.19(12) . . ?
C10 C9 H9A 117.8 . . ?
C10 C9 H9B 117.8 . . ?
C8 C10 H10A 117.7 . . ?
C8 C10 H10B 117.7 . . ?
C9 C10 C8 60.91(12) . . ?
C9 C10 H10A 117.7 . . ?
C9 C10 H10B 117.7 . . ?
H10A C10 H10B 114.8 . . ?
C12 C11 H11 119.8 . . ?
C12 C11 C16 120.43(16) . . ?
C16 C11 H11 119.8 . . ?
C11 C12 H12 120.1 . . ?
C11 C12 C13 119.79(16) . . ?
C13 C12 H12 120.1 . . ?
C12 C13 N3 119.15(17) . . ?
C12 C13 C14 121.17(16) . . ?
C14 C13 N3 119.66(17) . . ?
C13 C14 H14 120.3 . . ?
C15 C14 C13 119.48(17) . . ?
C15 C14 H14 120.3 . . ?
C14 C15 H15 119.7 . . ?
C14 C15 C16 120.62(16) . . ?
C16 C15 H15 119.7 . . ?
N1 C16 C11 120.94(15) . . ?
N1 C16 C15 120.63(14) . . ?
C15 C16 C11 118.43(15) . . ?
N1 C17 C8 99.53(12) . . ?
N1 C17 H17 110.5 . . ?
N1 C17 C18 111.37(13) . . ?
C8 C17 H17 110.5 . . ?
C8 C17 C18 114.07(13) . . ?
C18 C17 H17 110.5 . . ?
C19 C18 C17 107.81(14) . . ?
C19 C18 C22 104.60(14) . . ?
C19 C18 C23 112.13(14) . . ?
C22 C18 C17 110.97(14) . . ?
C23 C18 C17 112.43(13) . . ?
C23 C18 C22 108.63(15) . . ?
O3 C19 C18 110.80(15) . . ?
O4 C19 O3 122.95(17) . . ?
O4 C19 C18 126.14(17) . . ?
O3 C20 H20A 110.0 . . ?
O3 C20 H20B 110.0 . . ?
O3 C20 C21 108.27(17) . . ?
H20A C20 H20B 108.4 . . ?
C21 C20 H20A 110.0 . . ?
C21 C20 H20B 110.0 . . ?
F1 C21 C20 111.03(19) . . ?
F2 C21 F1 107.6(2) . . ?
F2 C21 C20 112.39(19) . . ?
F3 C21 F1 106.16(19) . . ?
F3 C21 F2 106.0(2) . . ?
F3 C21 C20 113.3(2) . . ?
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 . . ?
C18 C23 H23A 109.5 . . ?
C18 C23 H23B 109.5 . . ?
C18 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 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
O1 N3 C13 C12 161.0(2) . . . . ?
O1 N3 C13 C14 -17.3(3) . . . . ?
O2 N3 C13 C12 -16.6(3) . . . . ?
O2 N3 C13 C14 165.08(19) . . . . ?
O3 C20 C21 F1 -179.27(18) . . . . ?
O3 C20 C21 F2 -58.6(3) . . . . ?
O3 C20 C21 F3 61.4(2) . . . . ?
N1 N2 C7 C6 176.14(14) . . . . ?
N1 N2 C7 C8 -6.13(19) . . . . ?
N1 C17 C18 C19 -168.34(13) . . . . ?
N1 C17 C18 C22 -54.33(18) . . . . ?
N1 C17 C18 C23 67.56(18) . . . . ?
N2 N1 C16 C11 -175.29(15) . . . . ?
N2 N1 C16 C15 5.2(2) . . . . ?
N2 N1 C17 C8 21.68(16) . . . . ?
N2 N1 C17 C18 -98.97(15) . . . . ?
N2 C7 C8 C9 -114.33(18) . . . . ?
N2 C7 C8 C10 175.75(18) . . . . ?
N2 C7 C8 C17 19.67(19) . . . . ?
N3 C13 C14 C15 179.43(17) . . . . ?
C1 C2 C3 C4 0.6(3) . . . . ?
C1 C6 C7 N2 -139.61(19) . . . . ?
C1 C6 C7 C8 43.1(3) . . . . ?
C2 C1 C6 C5 0.1(3) . . . . ?
C2 C1 C6 C7 176.14(18) . . . . ?
C2 C3 C4 C5 -0.5(3) . . . . ?
C3 C4 C5 C6 0.2(3) . . . . ?
C4 C5 C6 C1 0.0(3) . . . . ?
C4 C5 C6 C7 -176.06(18) . . . . ?
C5 C6 C7 N2 36.4(3) . . . . ?
C5 C6 C7 C8 -140.95(19) . . . . ?
C6 C1 C2 C3 -0.4(3) . . . . ?
C6 C7 C8 C9 63.1(2) . . . . ?
C6 C7 C8 C10 -6.8(3) . . . . ?
C6 C7 C8 C17 -162.85(17) . . . . ?
C7 C8 C9 C10 -119.46(17) . . . . ?
C7 C8 C10 C9 101.4(2) . . . . ?
C7 C8 C17 N1 -23.07(15) . . . . ?
C7 C8 C17 C18 95.60(15) . . . . ?
C8 C17 C18 C19 79.98(16) . . . . ?
C8 C17 C18 C22 -166.02(14) . . . . ?
C8 C17 C18 C23 -44.13(19) . . . . ?
C9 C8 C17 N1 108.82(17) . . . . ?
C9 C8 C17 C18 -132.51(17) . . . . ?
C10 C8 C17 N1 -179.98(17) . . . . ?
C10 C8 C17 C18 -61.3(2) . . . . ?
C11 C12 C13 N3 -176.94(17) . . . . ?
C11 C12 C13 C14 1.3(3) . . . . ?
C12 C11 C16 N1 -178.97(16) . . . . ?
C12 C11 C16 C15 0.5(3) . . . . ?
C12 C13 C14 C15 1.2(3) . . . . ?
C13 C14 C15 C16 -2.8(3) . . . . ?
C14 C15 C16 N1 -178.51(16) . . . . ?
C14 C15 C16 C11 2.0(3) . . . . ?
C16 N1 N2 C7 149.44(15) . . . . ?
C16 N1 C17 C8 -136.17(16) . . . . ?
C16 N1 C17 C18 103.18(18) . . . . ?
C16 C11 C12 C13 -2.2(3) . . . . ?
C17 N1 N2 C7 -10.81(19) . . . . ?
C17 N1 C16 C11 -18.7(3) . . . . ?
C17 N1 C16 C15 161.77(16) . . . . ?
C17 C8 C9 C10 114.82(17) . . . . ?
C17 C8 C10 C9 -107.34(19) . . . . ?
C17 C18 C19 O3 -160.90(14) . . . . ?
C17 C18 C19 O4 22.9(2) . . . . ?
C19 O3 C20 C21 98.0(2) . . . . ?
C20 O3 C19 O4 9.6(3) . . . . ?
C20 O3 C19 C18 -166.68(14) . . . . ?
C22 C18 C19 O3 80.92(17) . . . . ?
C22 C18 C19 O4 -95.2(2) . . . . ?
C23 C18 C19 O3 -36.61(19) . . . . ?
C23 C18 C19 O4 147.2(2) . . . . ?

_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 6.941
_oxdiff_exptl_absorpt_empirical_full_min 0.431
