# Electronic Supplementary Material (ESI) for Green Chemistry.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_2605_auto
_database_code_depnum_ccdc_archive 'CCDC 2236364'
loop_
_audit_author_name
_audit_author_address
'Panyi Huang'
;Zhejiang University of Technology
China
;
_audit_update_record             
;
2023-01-16 deposited with the CCDC.	2023-04-12 downloaded from the CCDC.
;
_audit_creation_date             2023-01-06
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        1
_chemical_formula_moiety         'C20 H14 F5 N O3'
_chemical_formula_sum            'C20 H14 F5 N O3'
_chemical_formula_weight         411.32
_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'
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           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   17.1352(4)
_cell_length_b                   7.89497(16)
_cell_length_c                   14.2824(4)
_cell_angle_alpha                90
_cell_angle_beta                 110.302(3)
_cell_angle_gamma                90
_cell_volume                     1812.11(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6843
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      67.9210
_cell_measurement_theta_min      2.7390
_shelx_estimated_absorpt_T_max   0.943
_shelx_estimated_absorpt_T_min   0.921
_exptl_absorpt_coefficient_mu    1.188
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.09135
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.89a (Rigaku Oxford Diffraction, 2020)
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    1.508
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             840
_exptl_crystal_size_max          0.07
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0905
_diffrn_reflns_av_unetI/netI     0.0587
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            13174
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.112
_diffrn_reflns_theta_min         2.750
_diffrn_ambient_temperature      293
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -18.00   8.00   0.50    0.50    --   42.30 -77.00  60.00   52
  2  ω      0.00  66.00   0.50    0.50    --   42.30 -65.00  90.00  132
  3  ω     54.00  80.00   0.50    0.50    --   42.30  65.00 -30.00   52
  4  ω     11.00  37.00   0.50    0.50    --   42.30 -77.00  60.00   52
  5  ω    -16.00  68.00   0.50    0.50    --   42.30 -77.00-180.00  168
  6  ω     57.00 124.00   0.50    0.50    --   42.30  77.00 -90.00  134
  7  ω      2.00  64.00   0.50    0.50    --   42.30 -65.00-150.00  124
  8  ω     92.00 130.00   0.50    0.50    --   42.30  65.00 -30.00   76
  9  ω     39.00  69.00   0.50    0.50    --   42.30 -82.00  60.00   60
 10  ω    -31.00  -6.00   0.50    0.50    --   42.30 -82.00 -30.00   50
 11  ω    -23.00  16.00   0.50    0.50    --   42.30 -82.00-120.00   78
 12  ω    -44.00 -19.00   0.50    0.50    --   42.30 -77.00-180.00   50
 13  ω     45.00  70.00   0.50    0.50    --   42.30 -82.00-120.00   50
 14  ω     27.00  67.00   0.50    0.50    --   42.30 -65.00 -90.00   80
 15  ω    -45.00  -5.00   0.50    0.50    --   42.30 -65.00 -90.00   80
 16  ω    -45.00  26.00   0.50    0.50    --   42.30 -82.00  60.00  142
 17  ω    -43.00 -17.00   0.50    0.50    --   42.30 -65.00  90.00   52
 18  ω    -42.00 -17.00   0.50    0.50    --   42.30 -43.00   0.00   50
 19  ω    -11.00  70.00   0.50    0.50    --   42.30 -43.00   0.00  162
 20  ω     30.00  70.00   0.50    0.50    --   42.30 -82.00 -30.00   80
 21  ω     37.00 124.00   0.50    0.50    --   93.70 -42.00 -60.00  174
 22  ω     44.00  98.00   0.50    0.50    --   93.70 -82.00-120.00  108
 23  ω     64.00 118.00   0.50    0.50    --   93.70 -50.00-150.00  108
 24  ω     76.00 108.00   0.50    0.50    --   93.70 -59.00  90.00   64
 25  ω    126.00 166.00   0.50    0.50    --   93.70  33.00 -30.00   80
 26  ω     27.00  53.00   0.50    0.50    --   93.70 -59.00  90.00   52
 27  ω     61.00 108.00   0.50    0.50    --   93.70  33.00 -30.00   94
 28  ω      4.00  51.00   0.50    0.50    --   93.70 -50.00-150.00   94
 29  ω     77.00 103.00   0.50    0.50    --   93.70 -77.00 -90.00   52
 30  ω     79.00 110.00   0.50    0.50    --   93.70 -82.00-180.00   62
 31  ω     39.00  92.00   0.50    0.50    --   93.70 -82.00 -30.00  106
 32  ω     66.00  92.00   0.50    0.50    --   93.70 -82.00  90.00   52
 33  ω    139.00 165.00   0.50    0.50    --   93.70  82.00-150.00   52
 34  ω    104.00 130.00   0.50    0.50    --   93.70  82.00-150.00   52
 35  ω     60.00  99.00   0.50    0.50    --   93.70 -82.00  60.00   78
 36  ω     47.00 112.00   0.50    0.50    --   93.70 -59.00   0.00  130
 37  ω      4.00  98.00   0.50    0.50    --   93.70 -82.00-150.00  188
 38  ω     53.00 106.00   0.50    0.50    --   93.70 -82.00   0.00  106
 39  ω    138.00 164.00   0.50    0.50    --   93.70 -17.00  60.00   52
 40  ω     71.00 101.00   0.50    0.50    --   93.70 -82.00 -90.00   60
 41  ω    108.00 134.00   0.50    0.50    --   93.70 -17.00  60.00   52
 42  ω     48.00 109.00   0.50    0.50    --   93.70 -82.00 120.00  122
 43  ω      4.00  91.00   0.50    0.50    --   93.70 -17.00  60.00  174
 44  ω      4.00  29.00   0.50    0.50    --   93.70 -17.00 -90.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Pro II AFC12 (RINC): Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0262152000
_diffrn_orient_matrix_UB_12      -0.1097253000
_diffrn_orient_matrix_UB_13      0.0732674000
_diffrn_orient_matrix_UB_21      -0.0479086000
_diffrn_orient_matrix_UB_22      -0.1190642000
_diffrn_orient_matrix_UB_23      -0.0862388000
_diffrn_orient_matrix_UB_31      0.0787850000
_diffrn_orient_matrix_UB_32      -0.1089387000
_diffrn_orient_matrix_UB_33      0.0205028000
_diffrn_oxdiff_digest_frames     
;
01e7fff6b3130d25e53b9ccbc1e543ae0a000299d14
;
_diffrn_oxdiff_digest_hkl        
;
01dc9fa24fc2036fef51f75b0b53be08510612
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed 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                2582
_reflns_number_total             3278
_reflns_odcompleteness_completeness 99.17
_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 1.171.41.89a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.89a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.89a (Rigaku OD, 2020)'
_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         0.316
_refine_diff_density_min         -0.311
_refine_diff_density_rms         0.069
_refine_ls_extinction_coef       0.0016(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     290
_refine_ls_number_reflns         3278
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0739
_refine_ls_R_factor_gt           0.0662
_refine_ls_restrained_S_all      1.027
_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)+(0.1412P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1892
_refine_ls_wR_factor_ref         0.1987
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Others
 Fixed Sof: F1A(0.5) F2A(0.5) F3A(0.5) F1B(0.5) F2B(0.5) F3B(0.5)
3.a Ternary CH refined with riding coordinates:
 C8(H8), C11(H11)
3.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C12(H12A,H12B)
3.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C15(H15), C16(H16), C17(H17), C19(H19)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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
F4 F 0.55823(7) 0.15383(14) 0.80696(9) 0.0521(4) Uani 1 1 d . . . . .
F5 F 0.55739(7) 0.42172(15) 0.84068(9) 0.0559(4) Uani 1 1 d . . . . .
F1A F 0.1171(6) 0.3652(11) 0.5979(10) 0.122(2) Uani 0.5 1 d . . P A 1
F2A F 0.0456(3) 0.222(3) 0.4741(5) 0.142(5) Uani 0.5 1 d . . P A 1
F3A F 0.1167(6) 0.0997(13) 0.6029(10) 0.127(3) Uani 0.5 1 d . . P A 1
F1B F 0.1339(4) 0.230(4) 0.6380(6) 0.218(8) Uani 0.5 1 d . . P A 2
F2B F 0.0712(9) 0.3667(14) 0.5133(19) 0.183(4) Uani 0.5 1 d . . P A 2
F3B F 0.0612(9) 0.1189(19) 0.5049(17) 0.196(7) Uani 0.5 1 d . . P A 2
O1 O 0.79041(11) 0.2309(3) 0.80532(14) 0.0862(7) Uani 1 1 d . . . . .
O2 O 0.63374(10) 0.3740(3) 0.53011(13) 0.0700(5) Uani 1 1 d . . . . .
O5 O 0.39274(10) 0.3038(2) 0.76909(13) 0.0636(5) Uani 1 1 d . . . . .
N1 N 0.41736(10) 0.28487(18) 0.61973(13) 0.0404(4) Uani 1 1 d . . . . .
C1 C 0.82042(14) 0.2488(4) 0.7298(2) 0.0686(7) Uani 1 1 d . . . . .
C2 C 0.90441(17) 0.2108(5) 0.7500(3) 0.0960(11) Uani 1 1 d . . . . .
H2 H 0.937491 0.173349 0.813050 0.115 Uiso 1 1 calc R . . . .
C3 C 0.93719(19) 0.2291(6) 0.6763(3) 0.1084(13) Uani 1 1 d . . . . .
H3 H 0.993035 0.203781 0.689816 0.130 Uiso 1 1 calc R . . . .
C4 C 0.8896(2) 0.2844(5) 0.5821(3) 0.1006(12) Uani 1 1 d . . . . .
H4 H 0.913446 0.298199 0.533162 0.121 Uiso 1 1 calc R . . . .
C5 C 0.80603(16) 0.3192(4) 0.5611(2) 0.0763(8) Uani 1 1 d . . . . .
H5 H 0.773530 0.355681 0.497614 0.092 Uiso 1 1 calc R . . . .
C6 C 0.77031(13) 0.2999(3) 0.63448(19) 0.0579(6) Uani 1 1 d . . . . .
C7 C 0.67936(12) 0.3222(3) 0.61008(17) 0.0491(5) Uani 1 1 d . . . . .
C8 C 0.64825(13) 0.2707(3) 0.69291(17) 0.0482(5) Uani 1 1 d . . . . .
H8 H 0.643043 0.147025 0.691875 0.058 Uiso 1 1 calc R . . . .
C9 C 0.71470(15) 0.3214(4) 0.7911(2) 0.0718(8) Uani 1 1 d . . . . .
H9A H 0.724970 0.442172 0.790946 0.086 Uiso 1 1 calc R . . . .
H9B H 0.695257 0.296977 0.845889 0.086 Uiso 1 1 calc R . . . .
C10 C 0.53202(12) 0.3089(2) 0.76409(16) 0.0420(5) Uani 1 1 d . . . . .
C11 C 0.56310(11) 0.3466(2) 0.67974(15) 0.0430(5) Uani 1 1 d . . . . .
H11 H 0.567009 0.469806 0.674410 0.052 Uiso 1 1 calc R . . . .
C12 C 0.49100(12) 0.2839(2) 0.58850(16) 0.0441(5) Uani 1 1 d . . . . .
H12A H 0.482649 0.358739 0.531981 0.053 Uiso 1 1 calc R . . . .
H12B H 0.501988 0.170529 0.570045 0.053 Uiso 1 1 calc R . . . .
C13 C 0.43737(13) 0.3018(2) 0.71915(16) 0.0443(5) Uani 1 1 d . . . . .
C14 C 0.33676(12) 0.2518(2) 0.55018(16) 0.0434(5) Uani 1 1 d . . . . .
C15 C 0.32695(14) 0.2057(3) 0.45336(18) 0.0553(6) Uani 1 1 d . . . . .
H15 H 0.373335 0.198010 0.433971 0.066 Uiso 1 1 calc R . . . .
C16 C 0.24892(16) 0.1710(4) 0.3851(2) 0.0702(7) Uani 1 1 d . . . . .
H16 H 0.243060 0.142621 0.319851 0.084 Uiso 1 1 calc R . . . .
C17 C 0.17913(16) 0.1783(4) 0.4133(2) 0.0724(7) Uani 1 1 d . . . . .
H17 H 0.126623 0.152970 0.367959 0.087 Uiso 1 1 calc R . . . .
C18 C 0.18941(14) 0.2237(3) 0.5099(2) 0.0627(6) Uani 1 1 d . . . . .
C19 C 0.26691(13) 0.2616(3) 0.57917(18) 0.0543(6) Uani 1 1 d . . . . .
H19 H 0.272358 0.293079 0.643881 0.065 Uiso 1 1 calc R . . . .
C20 C 0.11580(18) 0.2296(5) 0.5442(3) 0.0849(9) 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
F4 C10 1.373(2) . ?
F5 C10 1.360(2) . ?
F1A C20 1.312(8) . ?
F2A C20 1.272(6) . ?
F3A C20 1.322(7) . ?
F1B C20 1.265(8) . ?
F2B C20 1.310(9) . ?
F3B C20 1.261(9) . ?
O1 C1 1.354(3) . ?
O1 C9 1.432(3) . ?
O2 C7 1.210(3) . ?
O5 C13 1.213(2) . ?
N1 C12 1.477(2) . ?
N1 C13 1.347(3) . ?
N1 C14 1.418(3) . ?
C1 C2 1.399(4) . ?
C1 C6 1.394(4) . ?
C2 H2 0.9300 . ?
C2 C3 1.362(5) . ?
C3 H3 0.9300 . ?
C3 C4 1.380(6) . ?
C4 H4 0.9300 . ?
C4 C5 1.385(4) . ?
C5 H5 0.9300 . ?
C5 C6 1.393(4) . ?
C6 C7 1.485(3) . ?
C7 C8 1.512(3) . ?
C8 H8 0.9800 . ?
C8 C9 1.522(4) . ?
C8 C11 1.527(3) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C11 1.506(3) . ?
C10 C13 1.524(3) . ?
C11 H11 0.9800 . ?
C11 C12 1.534(3) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C14 C15 1.382(3) . ?
C14 C19 1.398(3) . ?
C15 H15 0.9300 . ?
C15 C16 1.381(3) . ?
C16 H16 0.9300 . ?
C16 C17 1.389(3) . ?
C17 H17 0.9300 . ?
C17 C18 1.375(4) . ?
C18 C19 1.386(3) . ?
C18 C20 1.505(4) . ?
C19 H19 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
C1 O1 C9 114.3(2) . . ?
C13 N1 C12 112.78(16) . . ?
C13 N1 C14 125.92(15) . . ?
C14 N1 C12 120.93(16) . . ?
O1 C1 C2 117.5(3) . . ?
O1 C1 C6 122.2(2) . . ?
C6 C1 C2 120.3(3) . . ?
C1 C2 H2 120.4 . . ?
C3 C2 C1 119.2(4) . . ?
C3 C2 H2 120.4 . . ?
C2 C3 H3 119.2 . . ?
C2 C3 C4 121.7(3) . . ?
C4 C3 H3 119.2 . . ?
C3 C4 H4 120.3 . . ?
C3 C4 C5 119.4(3) . . ?
C5 C4 H4 120.3 . . ?
C4 C5 H5 119.8 . . ?
C4 C5 C6 120.4(3) . . ?
C6 C5 H5 119.8 . . ?
C1 C6 C7 120.3(2) . . ?
C5 C6 C1 118.9(2) . . ?
C5 C6 C7 120.6(2) . . ?
O2 C7 C6 122.9(2) . . ?
O2 C7 C8 122.81(18) . . ?
C6 C7 C8 114.3(2) . . ?
C7 C8 H8 108.1 . . ?
C7 C8 C9 107.23(18) . . ?
C7 C8 C11 112.29(18) . . ?
C9 C8 H8 108.1 . . ?
C9 C8 C11 112.81(18) . . ?
C11 C8 H8 108.1 . . ?
O1 C9 C8 110.5(2) . . ?
O1 C9 H9A 109.5 . . ?
O1 C9 H9B 109.5 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 108.1 . . ?
F4 C10 C11 112.40(15) . . ?
F4 C10 C13 106.90(14) . . ?
F5 C10 F4 105.16(16) . . ?
F5 C10 C11 114.28(15) . . ?
F5 C10 C13 111.05(15) . . ?
C11 C10 C13 106.87(16) . . ?
C8 C11 H11 108.1 . . ?
C8 C11 C12 115.57(16) . . ?
C10 C11 C8 114.32(17) . . ?
C10 C11 H11 108.1 . . ?
C10 C11 C12 102.23(14) . . ?
C12 C11 H11 108.1 . . ?
N1 C12 C11 105.22(15) . . ?
N1 C12 H12A 110.7 . . ?
N1 C12 H12B 110.7 . . ?
C11 C12 H12A 110.7 . . ?
C11 C12 H12B 110.7 . . ?
H12A C12 H12B 108.8 . . ?
O5 C13 N1 129.7(2) . . ?
O5 C13 C10 123.2(2) . . ?
N1 C13 C10 106.98(16) . . ?
C15 C14 N1 120.00(17) . . ?
C15 C14 C19 119.4(2) . . ?
C19 C14 N1 120.55(19) . . ?
C14 C15 H15 119.7 . . ?
C16 C15 C14 120.6(2) . . ?
C16 C15 H15 119.7 . . ?
C15 C16 H16 119.8 . . ?
C15 C16 C17 120.5(2) . . ?
C17 C16 H16 119.8 . . ?
C16 C17 H17 120.7 . . ?
C18 C17 C16 118.5(2) . . ?
C18 C17 H17 120.7 . . ?
C17 C18 C19 122.0(2) . . ?
C17 C18 C20 120.3(2) . . ?
C19 C18 C20 117.7(2) . . ?
C14 C19 H19 120.6 . . ?
C18 C19 C14 118.9(2) . . ?
C18 C19 H19 120.6 . . ?
F1A C20 F3A 105.6(6) . . ?
F1A C20 C18 111.7(4) . . ?
F2A C20 F1A 108.7(6) . . ?
F2A C20 F3A 105.1(6) . . ?
F2A C20 C18 114.3(4) . . ?
F3A C20 C18 110.9(4) . . ?
F1B C20 F2B 104.9(8) . . ?
F1B C20 C18 114.8(4) . . ?
F2B C20 C18 111.9(4) . . ?
F3B C20 F1B 110.1(8) . . ?
F3B C20 F2B 99.6(7) . . ?
F3B C20 C18 114.2(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
F4 C10 C11 C8 -32.3(2) . . . . ?
F4 C10 C11 C12 93.36(18) . . . . ?
F4 C10 C13 O5 72.9(2) . . . . ?
F4 C10 C13 N1 -103.96(17) . . . . ?
F5 C10 C11 C8 87.5(2) . . . . ?
F5 C10 C11 C12 -146.88(16) . . . . ?
F5 C10 C13 O5 -41.2(2) . . . . ?
F5 C10 C13 N1 141.84(16) . . . . ?
O1 C1 C2 C3 -179.2(3) . . . . ?
O1 C1 C6 C5 178.6(2) . . . . ?
O1 C1 C6 C7 -5.4(4) . . . . ?
O2 C7 C8 C9 -144.4(2) . . . . ?
O2 C7 C8 C11 -19.9(3) . . . . ?
N1 C14 C15 C16 179.2(2) . . . . ?
N1 C14 C19 C18 -178.18(19) . . . . ?
C1 O1 C9 C8 55.7(3) . . . . ?
C1 C2 C3 C4 0.0(6) . . . . ?
C1 C6 C7 O2 176.4(2) . . . . ?
C1 C6 C7 C8 -5.0(3) . . . . ?
C2 C1 C6 C5 -2.7(4) . . . . ?
C2 C1 C6 C7 173.3(3) . . . . ?
C2 C3 C4 C5 -1.2(6) . . . . ?
C3 C4 C5 C6 0.5(6) . . . . ?
C4 C5 C6 C1 1.4(4) . . . . ?
C4 C5 C6 C7 -174.5(3) . . . . ?
C5 C6 C7 O2 -7.7(4) . . . . ?
C5 C6 C7 C8 170.9(2) . . . . ?
C6 C1 C2 C3 2.0(5) . . . . ?
C6 C7 C8 C9 37.0(3) . . . . ?
C6 C7 C8 C11 161.42(18) . . . . ?
C7 C8 C9 O1 -62.9(3) . . . . ?
C7 C8 C11 C10 -175.98(16) . . . . ?
C7 C8 C11 C12 65.7(2) . . . . ?
C8 C11 C12 N1 147.14(16) . . . . ?
C9 O1 C1 C2 160.7(3) . . . . ?
C9 O1 C1 C6 -20.6(4) . . . . ?
C9 C8 C11 C10 -54.7(2) . . . . ?
C9 C8 C11 C12 -172.95(19) . . . . ?
C10 C11 C12 N1 22.33(18) . . . . ?
C11 C8 C9 O1 172.9(2) . . . . ?
C11 C10 C13 O5 -166.50(18) . . . . ?
C11 C10 C13 N1 16.59(19) . . . . ?
C12 N1 C13 O5 -178.27(19) . . . . ?
C12 N1 C13 C10 -1.6(2) . . . . ?
C12 N1 C14 C15 4.8(3) . . . . ?
C12 N1 C14 C19 -176.64(17) . . . . ?
C13 N1 C12 C11 -13.5(2) . . . . ?
C13 N1 C14 C15 -167.80(18) . . . . ?
C13 N1 C14 C19 10.8(3) . . . . ?
C13 C10 C11 C8 -149.25(16) . . . . ?
C13 C10 C11 C12 -23.61(18) . . . . ?
C14 N1 C12 C11 172.98(15) . . . . ?
C14 N1 C13 O5 -5.2(3) . . . . ?
C14 N1 C13 C10 171.46(16) . . . . ?
C14 C15 C16 C17 -1.4(4) . . . . ?
C15 C14 C19 C18 0.4(3) . . . . ?
C15 C16 C17 C18 1.2(4) . . . . ?
C16 C17 C18 C19 -0.2(4) . . . . ?
C16 C17 C18 C20 -178.7(3) . . . . ?
C17 C18 C19 C14 -0.6(4) . . . . ?
C17 C18 C20 F1A -136.5(8) . . . . ?
C17 C18 C20 F2A -12.5(11) . . . . ?
C17 C18 C20 F3A 106.0(8) . . . . ?
C17 C18 C20 F1B 162.7(16) . . . . ?
C17 C18 C20 F2B -77.9(13) . . . . ?
C17 C18 C20 F3B 34.2(14) . . . . ?
C19 C14 C15 C16 0.6(3) . . . . ?
C19 C18 C20 F1A 44.9(8) . . . . ?
C19 C18 C20 F2A 168.9(11) . . . . ?
C19 C18 C20 F3A -72.6(8) . . . . ?
C19 C18 C20 F1B -15.9(16) . . . . ?
C19 C18 C20 F2B 103.5(13) . . . . ?
C19 C18 C20 F3B -144.4(13) . . . . ?
C20 C18 C19 C14 178.0(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 8.605
_oxdiff_exptl_absorpt_empirical_full_min 0.290
