# 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 
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data_zhaoyl240117_1_0ma
_database_code_depnum_ccdc_archive 'CCDC 2342741'
loop_
_audit_author_name
_audit_author_address
'Z.-G. Han'
;H
China
;
_audit_update_record             
;
2024-03-24 deposited with the CCDC.	2024-04-25 downloaded from the CCDC.
;
_audit_creation_date             2024-03-11
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.06.28 svn.raecde09e for OlexSys, GUI svn.r6132)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H16 F3 N O4'
_chemical_formula_sum            'C21 H16 F3 N O4'
_chemical_formula_weight         403.35
_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                   17.477(8)
_cell_length_b                   7.987(4)
_cell_length_c                   13.665(7)
_cell_angle_alpha                90
_cell_angle_beta                 99.11(3)
_cell_angle_gamma                90
_cell_volume                     1883.5(17)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4157
_cell_measurement_temperature    295.01
_cell_measurement_theta_max      63.81
_cell_measurement_theta_min      4.47
_shelx_estimated_absorpt_T_max   0.879
_shelx_estimated_absorpt_T_min   0.863
_exptl_absorpt_coefficient_mu    1.015
_exptl_absorpt_correction_T_max  0.876
_exptl_absorpt_correction_T_min  0.859
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1203 before and 0.0558 after correction.
The Ratio of minimum to maximum transmission is 0.8028.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.422
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             832
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.13
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0384
_diffrn_reflns_av_unetI/netI     0.0314
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            14672
_diffrn_reflns_point_group_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        64.526
_diffrn_reflns_theta_max         64.526
_diffrn_reflns_theta_min         2.560
_diffrn_ambient_temperature      295.01
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2529
_reflns_number_total             3176
_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       'SAINT V8.38A (Bruker, 2018)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_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    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.373
_refine_diff_density_min         -0.318
_refine_diff_density_rms         0.072
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.122
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     263
_refine_ls_number_reflns         3126
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0649
_refine_ls_R_factor_gt           0.0519
_refine_ls_restrained_S_all      1.122
_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)+(0.0672P)²+0.6330P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1306
_refine_ls_wR_factor_ref         0.1410
_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:
 C6(H6), C14(H14)
2.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B)
2.c Aromatic/amide H refined with riding coordinates:
 C9(H9), C10(H10), C11(H11), C17(H17), C18(H18), C21(H21), C22(H22), C23(H23),
 C24(H24)
2.d Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C)
;
_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
O1 O 0.36426(8) 0.65570(19) 0.46013(12) 0.0552(4) Uani 1 1 d . . . . .
O2 O 0.40058(8) 0.3245(2) 0.61039(13) 0.0659(5) Uani 1 1 d . . . . .
O3 O 0.33655(9) 0.2220(2) 0.72713(12) 0.0619(4) Uani 1 1 d . . . . .
O4 O 0.39255(10) 0.7093(3) 0.62400(13) 0.0753(5) Uani 1 1 d . . . . .
N1 N 0.11561(9) 0.5124(2) 0.46080(13) 0.0477(5) Uani 1 1 d . . . . .
F1 F 0.35182(12) 0.9057(3) 0.32139(13) 0.1112(7) Uani 1 1 d . . . . .
C2 C 0.40576(15) 0.9137(3) 0.4010(2) 0.0645(7) Uani 1 1 d . . . . .
C3 C 0.43111(13) 0.7475(3) 0.4419(2) 0.0613(7) Uani 1 1 d . . . . .
H3A H 0.457215 0.687117 0.395167 0.074 Uiso 1 1 calc R U . . .
H3B H 0.467104 0.760842 0.503166 0.074 Uiso 1 1 calc R U . . .
C4 C 0.35081(12) 0.6494(3) 0.55524(17) 0.0487(5) Uani 1 1 d . . . . .
C5 C 0.27348(11) 0.5703(3) 0.55932(15) 0.0416(5) Uani 1 1 d . . . . .
C6 C 0.24960(10) 0.4172(2) 0.49834(15) 0.0413(5) Uani 1 1 d . . . . .
H6 H 0.288356 0.372811 0.460654 0.050 Uiso 1 1 calc R U . . .
C7 C 0.16793(11) 0.4047(3) 0.44893(15) 0.0416(5) Uani 1 1 d . . . . .
C8 C 0.14688(10) 0.2600(3) 0.38242(14) 0.0421(5) Uani 1 1 d . . . . .
C9 C 0.18798(12) 0.1107(3) 0.39533(17) 0.0528(6) Uani 1 1 d . . . . .
H9 H 0.230854 0.102857 0.444994 0.063 Uiso 1 1 calc R U . . .
C10 C 0.16636(14) -0.0261(3) 0.33584(19) 0.0623(6) Uani 1 1 d . . . . .
H10 H 0.193744 -0.125959 0.346711 0.075 Uiso 1 1 calc R U . . .
C11 C 0.10469(15) -0.0151(4) 0.2609(2) 0.0664(7) Uani 1 1 d . . . . .
H11 H 0.090378 -0.107315 0.220557 0.080 Uiso 1 1 calc R U . . .
F12 F 0.37554(11) 1.0059(2) 0.46627(14) 0.0936(6) Uani 1 1 d . . . . .
F13 F 0.46544(11) 0.9991(2) 0.37679(16) 0.0993(6) Uani 1 1 d . . . . .
C14 C 0.26999(11) 0.4028(3) 0.61121(15) 0.0425(5) Uani 1 1 d . . . . .
H14 H 0.226872 0.385760 0.648081 0.051 Uiso 1 1 calc R U . . .
C15 C 0.34299(12) 0.3144(3) 0.64792(16) 0.0463(5) Uani 1 1 d . . . . .
C16 C 0.40423(16) 0.1265(4) 0.7689(2) 0.0809(8) Uani 1 1 d . . . . .
H16A H 0.412469 0.037910 0.724183 0.121 Uiso 1 1 calc R U . . .
H16B H 0.396409 0.079511 0.831195 0.121 Uiso 1 1 calc R U . . .
H16C H 0.448731 0.198565 0.778919 0.121 Uiso 1 1 calc R U . . .
C17 C 0.06391(15) 0.1316(4) 0.24499(19) 0.0705(8) Uani 1 1 d . . . . .
H17 H 0.022439 0.139240 0.193349 0.085 Uiso 1 1 calc R U . . .
C18 C 0.08447(12) 0.2693(3) 0.30604(17) 0.0578(6) Uani 1 1 d . . . . .
H18 H 0.056183 0.368067 0.295543 0.069 Uiso 1 1 calc R U . . .
C19 C 0.13489(12) 0.6541(3) 0.52149(16) 0.0461(5) Uani 1 1 d . . . . .
C20 C 0.20980(11) 0.6915(3) 0.56912(15) 0.0449(5) Uani 1 1 d . . . . .
C21 C 0.22265(14) 0.8373(3) 0.62507(19) 0.0580(6) Uani 1 1 d . . . . .
H21 H 0.272429 0.863176 0.656405 0.070 Uiso 1 1 calc R U . . .
C22 C 0.16200(17) 0.9437(3) 0.6344(2) 0.0684(7) Uani 1 1 d . . . . .
H22 H 0.171171 1.041528 0.671256 0.082 Uiso 1 1 calc R U . . .
C23 C 0.08808(16) 0.9056(3) 0.5893(2) 0.0671(7) Uani 1 1 d . . . . .
H23 H 0.047208 0.976495 0.596807 0.081 Uiso 1 1 calc R U . . .
C24 C 0.07444(13) 0.7627(3) 0.53293(18) 0.0571(6) Uani 1 1 d . . . . .
H24 H 0.024351 0.738198 0.502150 0.069 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
O1 C3 1.434(2) . ?
O1 C4 1.358(3) . ?
O2 C15 1.202(3) . ?
O3 C15 1.330(3) . ?
O3 C16 1.447(3) . ?
O4 C4 1.194(3) . ?
N1 C7 1.284(3) . ?
N1 C19 1.412(3) . ?
F1 C2 1.324(3) . ?
C2 C3 1.481(4) . ?
C2 F12 1.328(3) . ?
C2 F13 1.331(3) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C5 1.501(3) . ?
C5 C6 1.501(3) . ?
C5 C14 1.520(3) . ?
C5 C20 1.497(3) . ?
C6 H6 0.9800 . ?
C6 C7 1.482(3) . ?
C6 C14 1.531(3) . ?
C7 C8 1.480(3) . ?
C8 C9 1.389(3) . ?
C8 C18 1.387(3) . ?
C9 H9 0.9300 . ?
C9 C10 1.378(3) . ?
C10 H10 0.9300 . ?
C10 C11 1.367(4) . ?
C11 H11 0.9300 . ?
C11 C17 1.371(4) . ?
C14 H14 0.9800 . ?
C14 C15 1.475(3) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 H17 0.9300 . ?
C17 C18 1.393(4) . ?
C18 H18 0.9300 . ?
C19 C20 1.399(3) . ?
C19 C24 1.394(3) . ?
C20 C21 1.392(3) . ?
C21 H21 0.9300 . ?
C21 C22 1.380(3) . ?
C22 H22 0.9300 . ?
C22 C23 1.375(4) . ?
C23 H23 0.9300 . ?
C23 C24 1.376(4) . ?
C24 H24 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 O1 C3 117.02(18) . . ?
C15 O3 C16 116.40(19) . . ?
C7 N1 C19 120.17(17) . . ?
F1 C2 C3 113.5(2) . . ?
F1 C2 F12 105.8(2) . . ?
F1 C2 F13 107.7(2) . . ?
F12 C2 C3 111.8(2) . . ?
F12 C2 F13 107.1(2) . . ?
F13 C2 C3 110.7(2) . . ?
O1 C3 C2 108.69(19) . . ?
O1 C3 H3A 110.0 . . ?
O1 C3 H3B 110.0 . . ?
C2 C3 H3A 110.0 . . ?
C2 C3 H3B 110.0 . . ?
H3A C3 H3B 108.3 . . ?
O1 C4 C5 110.15(18) . . ?
O4 C4 O1 124.17(19) . . ?
O4 C4 C5 125.5(2) . . ?
C4 C5 C14 119.41(17) . . ?
C6 C5 C4 119.69(17) . . ?
C6 C5 C14 60.93(14) . . ?
C20 C5 C4 114.66(17) . . ?
C20 C5 C6 115.54(16) . . ?
C20 C5 C14 116.25(16) . . ?
C5 C6 H6 115.6 . . ?
C5 C6 C14 60.15(13) . . ?
C7 C6 C5 118.09(17) . . ?
C7 C6 H6 115.6 . . ?
C7 C6 C14 120.49(16) . . ?
C14 C6 H6 115.6 . . ?
N1 C7 C6 123.42(19) . . ?
N1 C7 C8 119.19(17) . . ?
C8 C7 C6 117.39(17) . . ?
C9 C8 C7 121.27(18) . . ?
C18 C8 C7 120.6(2) . . ?
C18 C8 C9 118.1(2) . . ?
C8 C9 H9 119.4 . . ?
C10 C9 C8 121.2(2) . . ?
C10 C9 H9 119.4 . . ?
C9 C10 H10 120.0 . . ?
C11 C10 C9 120.1(2) . . ?
C11 C10 H10 120.0 . . ?
C10 C11 H11 119.9 . . ?
C10 C11 C17 120.1(2) . . ?
C17 C11 H11 119.9 . . ?
C5 C14 C6 58.93(13) . . ?
C5 C14 H14 116.9 . . ?
C6 C14 H14 116.9 . . ?
C15 C14 C5 118.91(17) . . ?
C15 C14 C6 115.43(17) . . ?
C15 C14 H14 116.9 . . ?
O2 C15 O3 124.66(19) . . ?
O2 C15 C14 124.1(2) . . ?
O3 C15 C14 111.26(17) . . ?
O3 C16 H16A 109.5 . . ?
O3 C16 H16B 109.5 . . ?
O3 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C11 C17 H17 119.9 . . ?
C11 C17 C18 120.1(2) . . ?
C18 C17 H17 119.9 . . ?
C8 C18 C17 120.4(2) . . ?
C8 C18 H18 119.8 . . ?
C17 C18 H18 119.8 . . ?
C20 C19 N1 124.26(18) . . ?
C24 C19 N1 116.7(2) . . ?
C24 C19 C20 119.0(2) . . ?
C19 C20 C5 118.33(18) . . ?
C21 C20 C5 122.19(19) . . ?
C21 C20 C19 119.5(2) . . ?
C20 C21 H21 119.8 . . ?
C22 C21 C20 120.4(2) . . ?
C22 C21 H21 119.8 . . ?
C21 C22 H22 119.9 . . ?
C23 C22 C21 120.2(2) . . ?
C23 C22 H22 119.9 . . ?
C22 C23 H23 119.9 . . ?
C22 C23 C24 120.1(2) . . ?
C24 C23 H23 119.9 . . ?
C19 C24 H24 119.6 . . ?
C23 C24 C19 120.7(2) . . ?
C23 C24 H24 119.6 . . ?

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 C4 C5 C6 42.9(3) . . . . ?
O1 C4 C5 C14 114.2(2) . . . . ?
O1 C4 C5 C20 -100.9(2) . . . . ?
O4 C4 C5 C6 -141.9(2) . . . . ?
O4 C4 C5 C14 -70.6(3) . . . . ?
O4 C4 C5 C20 74.2(3) . . . . ?
N1 C7 C8 C9 -153.9(2) . . . . ?
N1 C7 C8 C18 25.1(3) . . . . ?
N1 C19 C20 C5 -2.9(3) . . . . ?
N1 C19 C20 C21 178.21(19) . . . . ?
N1 C19 C24 C23 -178.8(2) . . . . ?
F1 C2 C3 O1 -54.6(3) . . . . ?
C3 O1 C4 O4 -3.1(3) . . . . ?
C3 O1 C4 C5 172.08(18) . . . . ?
C4 O1 C3 C2 -101.0(2) . . . . ?
C4 C5 C6 C7 -139.84(19) . . . . ?
C4 C5 C6 C14 109.3(2) . . . . ?
C4 C5 C14 C6 -109.7(2) . . . . ?
C4 C5 C14 C15 -5.8(3) . . . . ?
C4 C5 C20 C19 145.14(19) . . . . ?
C4 C5 C20 C21 -36.0(3) . . . . ?
C5 C6 C7 N1 -4.7(3) . . . . ?
C5 C6 C7 C8 175.05(17) . . . . ?
C5 C6 C14 C15 -109.79(19) . . . . ?
C5 C14 C15 O2 -30.1(3) . . . . ?
C5 C14 C15 O3 150.23(18) . . . . ?
C5 C20 C21 C22 -178.3(2) . . . . ?
C6 C5 C14 C15 103.9(2) . . . . ?
C6 C5 C20 C19 -0.3(3) . . . . ?
C6 C5 C20 C21 178.59(19) . . . . ?
C6 C7 C8 C9 26.4(3) . . . . ?
C6 C7 C8 C18 -154.63(19) . . . . ?
C6 C14 C15 O2 36.9(3) . . . . ?
C6 C14 C15 O3 -142.73(18) . . . . ?
C7 N1 C19 C20 2.3(3) . . . . ?
C7 N1 C19 C24 -178.21(19) . . . . ?
C7 C6 C14 C5 -107.0(2) . . . . ?
C7 C6 C14 C15 143.23(19) . . . . ?
C7 C8 C9 C10 177.3(2) . . . . ?
C7 C8 C18 C17 -178.6(2) . . . . ?
C8 C9 C10 C11 1.7(4) . . . . ?
C9 C8 C18 C17 0.4(3) . . . . ?
C9 C10 C11 C17 -0.4(4) . . . . ?
C10 C11 C17 C18 -0.9(4) . . . . ?
C11 C17 C18 C8 0.9(4) . . . . ?
F12 C2 C3 O1 64.9(3) . . . . ?
F13 C2 C3 O1 -175.8(2) . . . . ?
C14 C5 C6 C7 110.90(19) . . . . ?
C14 C5 C20 C19 -68.9(2) . . . . ?
C14 C5 C20 C21 110.0(2) . . . . ?
C14 C6 C7 N1 65.4(3) . . . . ?
C14 C6 C7 C8 -114.9(2) . . . . ?
C16 O3 C15 O2 -0.8(3) . . . . ?
C16 O3 C15 C14 178.8(2) . . . . ?
C18 C8 C9 C10 -1.7(3) . . . . ?
C19 N1 C7 C6 1.7(3) . . . . ?
C19 N1 C7 C8 -178.05(17) . . . . ?
C19 C20 C21 C22 0.6(3) . . . . ?
C20 C5 C6 C7 3.7(3) . . . . ?
C20 C5 C6 C14 -107.17(19) . . . . ?
C20 C5 C14 C6 106.01(19) . . . . ?
C20 C5 C14 C15 -150.11(19) . . . . ?
C20 C19 C24 C23 0.7(3) . . . . ?
C20 C21 C22 C23 0.7(4) . . . . ?
C21 C22 C23 C24 -1.3(4) . . . . ?
C22 C23 C24 C19 0.6(4) . . . . ?
C24 C19 C20 C5 177.64(19) . . . . ?
C24 C19 C20 C21 -1.3(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_zhaoyl230222_2_0m
_database_code_depnum_ccdc_archive 'CCDC 2342742'
loop_
_audit_author_name
_audit_author_address
'Z.-G. Han'
;H
China
;
_audit_update_record             
;
2024-03-24 deposited with the CCDC.	2024-04-25 downloaded from the CCDC.
;
_audit_creation_date             2024-03-11
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.06.28 svn.raecde09e for OlexSys, GUI svn.r6132)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H16 F4 N O4'
_chemical_formula_sum            'C21 H16 F4 N O4'
_chemical_formula_weight         422.35
_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      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                   8.4608(7)
_cell_length_b                   9.0720(7)
_cell_length_c                   12.7643(11)
_cell_angle_alpha                83.426(4)
_cell_angle_beta                 87.516(5)
_cell_angle_gamma                75.395(4)
_cell_volume                     941.74(14)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    6174
_cell_measurement_temperature    273.15
_cell_measurement_theta_max      63.93
_cell_measurement_theta_min      3.49
_shelx_estimated_absorpt_T_max   0.868
_shelx_estimated_absorpt_T_min   0.850
_exptl_absorpt_coefficient_mu    1.121
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.489
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             434
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.13
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0431
_diffrn_reflns_av_unetI/netI     0.0477
_diffrn_reflns_Laue_measured_fraction_full 0.976
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            8324
_diffrn_reflns_point_group_measured_fraction_full 0.976
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_theta_full        63.925
_diffrn_reflns_theta_max         63.925
_diffrn_reflns_theta_min         3.486
_diffrn_ambient_temperature      273.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.976
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2552
_reflns_number_total             3118
_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       'SAINT V8.38A (Bruker, 2018)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_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    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.356
_refine_diff_density_min         -0.583
_refine_diff_density_rms         0.130
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.123
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     272
_refine_ls_number_reflns         3042
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0761
_refine_ls_R_factor_gt           0.0657
_refine_ls_restrained_S_all      1.123
_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)+(0.0872P)²+0.4939P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1617
_refine_ls_wR_factor_ref         0.1725
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C5(H5), C17(H17)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B)
2.c Aromatic/amide H refined with riding coordinates:
 C8(H8), C9(H9), C10(H10), N1(H1), C13(H13), C15(H15), C16(H16), C18(H18),
 C19(H19)
2.d Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C)
;
_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
O1 O 0.6322(2) 0.8424(2) 0.75285(17) 0.0533(5) Uani 1 1 d . . . . .
F2 F 0.6354(2) 0.0828(2) 0.97299(18) 0.0767(6) Uani 1 1 d . . . . .
O2 O 1.0525(3) 0.2986(2) 0.75904(15) 0.0539(5) Uani 1 1 d . . . . .
O3 O 0.9875(2) 0.8061(2) 0.80575(14) 0.0476(5) Uani 1 1 d . . . . .
O4 O 0.9386(3) 0.7438(2) 0.97568(15) 0.0522(5) Uani 1 1 d . . . . .
F1 F 0.6434(3) 1.0132(3) 0.56507(18) 0.0975(8) Uani 1 1 d . . . . .
C1 C 0.5617(4) 1.0734(4) 0.6468(3) 0.0669(9) Uani 1 1 d . . . . .
C2 C 0.4955(4) 0.9626(3) 0.7176(3) 0.0649(9) Uani 1 1 d . . . . .
H2A H 0.437827 1.010875 0.777032 0.078 Uiso 1 1 calc R U . . .
H2B H 0.420401 0.922998 0.680243 0.078 Uiso 1 1 calc R U . . .
C3 C 0.5996(3) 0.7091(3) 0.7916(2) 0.0390(6) Uani 1 1 d . . . . .
C4 C 0.7395(3) 0.5749(3) 0.81744(18) 0.0331(5) Uani 1 1 d . . . . .
C5 C 0.8886(3) 0.5524(3) 0.74199(19) 0.0348(6) Uani 1 1 d . . . . .
H5 H 0.890860 0.639893 0.689758 0.042 Uiso 1 1 calc R U . . .
C6 C 0.9575(3) 0.3978(3) 0.70489(19) 0.0365(6) Uani 1 1 d . . . . .
C7 C 0.9040(3) 0.3713(3) 0.60082(19) 0.0366(6) Uani 1 1 d . . . . .
C8 C 0.9904(3) 0.2434(3) 0.5537(2) 0.0449(6) Uani 1 1 d . . . . .
H8 H 1.081333 0.177769 0.586860 0.054 Uiso 1 1 calc R U . . .
C9 C 0.9419(4) 0.2131(3) 0.4582(2) 0.0514(7) Uani 1 1 d . . . . .
H9 H 1.000684 0.127643 0.427154 0.062 Uiso 1 1 calc R U . . .
C10 C 0.8068(4) 0.3093(4) 0.4089(2) 0.0527(7) Uani 1 1 d . . . . .
H10 H 0.773838 0.288197 0.344821 0.063 Uiso 1 1 calc R U . . .
N1 N 0.4592(3) 0.6825(3) 0.80323(19) 0.0468(6) Uani 1 1 d . . . . .
H1 H 0.366492 0.746009 0.789286 0.056 Uiso 1 1 calc R U . . .
C11 C 0.4871(3) 0.5256(3) 0.8442(2) 0.0406(6) Uani 1 1 d . . . . .
C12 C 0.6532(3) 0.4560(3) 0.85625(18) 0.0346(6) Uani 1 1 d . . . . .
C13 C 0.7064(3) 0.3064(3) 0.9006(2) 0.0391(6) Uani 1 1 d . . . . .
H13 H 0.816617 0.259504 0.910787 0.047 Uiso 1 1 calc R U . . .
C14 C 0.5864(4) 0.2309(3) 0.9289(2) 0.0487(7) Uani 1 1 d . . . . .
C15 C 0.4228(4) 0.2939(4) 0.9162(3) 0.0562(8) Uani 1 1 d . . . . .
H15 H 0.347650 0.236423 0.936203 0.067 Uiso 1 1 calc R U . . .
C16 C 0.3710(3) 0.4448(4) 0.8730(3) 0.0554(8) Uani 1 1 d . . . . .
H16 H 0.260410 0.490815 0.863667 0.067 Uiso 1 1 calc R U . . .
C17 C 0.9086(3) 0.5768(3) 0.85308(19) 0.0323(5) Uani 1 1 d . . . . .
H17 H 0.962922 0.483114 0.896648 0.039 Uiso 1 1 calc R U . . .
C18 C 0.7206(4) 0.4366(4) 0.4544(2) 0.0560(8) Uani 1 1 d . . . . .
H18 H 0.629048 0.501164 0.421351 0.067 Uiso 1 1 calc R U . . .
C19 C 0.7703(3) 0.4684(3) 0.5494(2) 0.0484(7) Uani 1 1 d . . . . .
H19 H 0.713282 0.555857 0.579022 0.058 Uiso 1 1 calc R U . . .
C20 C 0.9441(3) 0.7182(3) 0.88568(19) 0.0336(5) Uani 1 1 d . . . . .
C21 C 1.0291(5) 0.9436(4) 0.8319(3) 0.0654(9) Uani 1 1 d . . . . .
H21A H 1.041462 1.007286 0.768241 0.098 Uiso 1 1 calc R U . . .
H21B H 1.129662 0.915304 0.869857 0.098 Uiso 1 1 calc R U . . .
H21C H 0.943570 0.998749 0.874949 0.098 Uiso 1 1 calc R U . . .
F24 F 0.6645(3) 1.1313(3) 0.6934(2) 0.1000(8) Uani 1 1 d . . . . .
F25 F 0.4412(3) 1.1873(3) 0.6077(3) 0.1223(10) 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
O1 C2 1.423(3) . ?
O1 C3 1.342(3) . ?
F2 C14 1.363(3) . ?
O2 C6 1.215(3) . ?
O3 C20 1.319(3) . ?
O3 C21 1.455(3) . ?
O4 C20 1.194(3) . ?
F1 C1 1.319(4) . ?
C1 C2 1.475(5) . ?
C1 F24 1.317(4) . ?
C1 F25 1.324(4) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.486(3) . ?
C3 N1 1.270(3) . ?
C4 C5 1.539(3) . ?
C4 C12 1.479(3) . ?
C4 C17 1.524(3) . ?
C5 H5 0.9800 . ?
C5 C6 1.499(3) . ?
C5 C17 1.483(3) . ?
C6 C7 1.486(3) . ?
C7 C8 1.392(4) . ?
C7 C19 1.383(4) . ?
C8 H8 0.9300 . ?
C8 C9 1.380(4) . ?
C9 H9 0.9300 . ?
C9 C10 1.378(4) . ?
C10 H10 0.9300 . ?
C10 C18 1.377(4) . ?
N1 H1 0.8600 . ?
N1 C11 1.423(4) . ?
C11 C12 1.395(3) . ?
C11 C16 1.381(4) . ?
C12 C13 1.379(4) . ?
C13 H13 0.9300 . ?
C13 C14 1.376(4) . ?
C14 C15 1.367(4) . ?
C15 H15 0.9300 . ?
C15 C16 1.384(4) . ?
C16 H16 0.9300 . ?
C17 H17 0.9800 . ?
C17 C20 1.495(3) . ?
C18 H18 0.9300 . ?
C18 C19 1.385(4) . ?
C19 H19 0.9300 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 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
C3 O1 C2 116.1(2) . . ?
C20 O3 C21 116.1(2) . . ?
F1 C1 C2 113.1(3) . . ?
F1 C1 F25 106.3(3) . . ?
F24 C1 F1 105.2(3) . . ?
F24 C1 C2 113.2(3) . . ?
F24 C1 F25 108.5(3) . . ?
F25 C1 C2 110.1(3) . . ?
O1 C2 C1 106.2(3) . . ?
O1 C2 H2A 110.5 . . ?
O1 C2 H2B 110.5 . . ?
C1 C2 H2A 110.5 . . ?
C1 C2 H2B 110.5 . . ?
H2A C2 H2B 108.7 . . ?
O1 C3 C4 118.1(2) . . ?
N1 C3 O1 126.4(2) . . ?
N1 C3 C4 115.4(2) . . ?
C3 C4 C5 117.9(2) . . ?
C3 C4 C17 127.2(2) . . ?
C12 C4 C3 101.00(19) . . ?
C12 C4 C5 125.4(2) . . ?
C12 C4 C17 124.3(2) . . ?
C17 C4 C5 57.91(15) . . ?
C4 C5 H5 115.4 . . ?
C6 C5 C4 119.0(2) . . ?
C6 C5 H5 115.4 . . ?
C17 C5 C4 60.54(15) . . ?
C17 C5 H5 115.4 . . ?
C17 C5 C6 120.2(2) . . ?
O2 C6 C5 120.6(2) . . ?
O2 C6 C7 121.9(2) . . ?
C7 C6 C5 117.5(2) . . ?
C8 C7 C6 118.8(2) . . ?
C19 C7 C6 122.4(2) . . ?
C19 C7 C8 118.7(2) . . ?
C7 C8 H8 119.8 . . ?
C9 C8 C7 120.5(3) . . ?
C9 C8 H8 119.8 . . ?
C8 C9 H9 119.9 . . ?
C10 C9 C8 120.2(3) . . ?
C10 C9 H9 119.9 . . ?
C9 C10 H10 120.0 . . ?
C18 C10 C9 119.9(3) . . ?
C18 C10 H10 120.0 . . ?
C3 N1 H1 127.2 . . ?
C3 N1 C11 105.7(2) . . ?
C11 N1 H1 127.2 . . ?
C12 C11 N1 111.9(2) . . ?
C16 C11 N1 127.2(2) . . ?
C16 C11 C12 120.8(3) . . ?
C11 C12 C4 105.9(2) . . ?
C13 C12 C4 132.9(2) . . ?
C13 C12 C11 121.2(2) . . ?
C12 C13 H13 122.1 . . ?
C14 C13 C12 115.9(2) . . ?
C14 C13 H13 122.1 . . ?
F2 C14 C13 117.2(3) . . ?
F2 C14 C15 118.2(2) . . ?
C15 C14 C13 124.6(3) . . ?
C14 C15 H15 120.6 . . ?
C14 C15 C16 118.9(3) . . ?
C16 C15 H15 120.6 . . ?
C11 C16 C15 118.5(3) . . ?
C11 C16 H16 120.7 . . ?
C15 C16 H16 120.7 . . ?
C4 C17 H17 113.3 . . ?
C5 C17 C4 61.54(15) . . ?
C5 C17 H17 113.3 . . ?
C5 C17 C20 123.9(2) . . ?
C20 C17 C4 121.91(19) . . ?
C20 C17 H17 113.3 . . ?
C10 C18 H18 120.0 . . ?
C10 C18 C19 120.0(3) . . ?
C19 C18 H18 120.0 . . ?
C7 C19 C18 120.7(3) . . ?
C7 C19 H19 119.7 . . ?
C18 C19 H19 119.7 . . ?
O3 C20 C17 112.9(2) . . ?
O4 C20 O3 124.6(2) . . ?
O4 C20 C17 122.4(2) . . ?
O3 C21 H21A 109.5 . . ?
O3 C21 H21B 109.5 . . ?
O3 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 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 C3 C4 C5 -39.6(3) . . . . ?
O1 C3 C4 C12 -180.0(2) . . . . ?
O1 C3 C4 C17 29.8(4) . . . . ?
O1 C3 N1 C11 178.6(2) . . . . ?
F2 C14 C15 C16 179.0(3) . . . . ?
O2 C6 C7 C8 -14.3(4) . . . . ?
O2 C6 C7 C19 165.0(3) . . . . ?
F1 C1 C2 O1 59.3(4) . . . . ?
C2 O1 C3 C4 172.9(2) . . . . ?
C2 O1 C3 N1 -2.8(4) . . . . ?
C3 O1 C2 C1 -160.6(3) . . . . ?
C3 C4 C5 C6 -131.2(2) . . . . ?
C3 C4 C5 C17 118.4(2) . . . . ?
C3 C4 C12 C11 3.0(2) . . . . ?
C3 C4 C12 C13 -174.6(3) . . . . ?
C3 C4 C17 C5 -102.6(3) . . . . ?
C3 C4 C17 C20 11.6(4) . . . . ?
C3 N1 C11 C12 -0.6(3) . . . . ?
C3 N1 C11 C16 177.7(3) . . . . ?
C4 C3 N1 C11 2.8(3) . . . . ?
C4 C5 C6 O2 -83.1(3) . . . . ?
C4 C5 C6 C7 96.4(3) . . . . ?
C4 C5 C17 C20 -111.1(2) . . . . ?
C4 C12 C13 C14 178.9(2) . . . . ?
C4 C17 C20 O3 -87.5(3) . . . . ?
C4 C17 C20 O4 94.9(3) . . . . ?
C5 C4 C12 C11 -133.3(2) . . . . ?
C5 C4 C12 C13 49.1(4) . . . . ?
C5 C4 C17 C20 114.2(3) . . . . ?
C5 C6 C7 C8 166.2(2) . . . . ?
C5 C6 C7 C19 -14.5(3) . . . . ?
C5 C17 C20 O3 -12.5(3) . . . . ?
C5 C17 C20 O4 170.0(2) . . . . ?
C6 C5 C17 C4 -108.4(2) . . . . ?
C6 C5 C17 C20 140.5(2) . . . . ?
C6 C7 C8 C9 178.5(2) . . . . ?
C6 C7 C19 C18 -177.5(3) . . . . ?
C7 C8 C9 C10 -0.3(4) . . . . ?
C8 C7 C19 C18 1.8(4) . . . . ?
C8 C9 C10 C18 0.6(4) . . . . ?
C9 C10 C18 C19 0.4(5) . . . . ?
C10 C18 C19 C7 -1.6(5) . . . . ?
N1 C3 C4 C5 136.6(2) . . . . ?
N1 C3 C4 C12 -3.8(3) . . . . ?
N1 C3 C4 C17 -154.0(2) . . . . ?
N1 C11 C12 C4 -1.7(3) . . . . ?
N1 C11 C12 C13 176.2(2) . . . . ?
N1 C11 C16 C15 -177.0(3) . . . . ?
C11 C12 C13 C14 1.7(4) . . . . ?
C12 C4 C5 C6 -1.4(4) . . . . ?
C12 C4 C5 C17 -111.7(3) . . . . ?
C12 C4 C17 C5 113.6(2) . . . . ?
C12 C4 C17 C20 -132.2(2) . . . . ?
C12 C11 C16 C15 1.3(4) . . . . ?
C12 C13 C14 F2 180.0(2) . . . . ?
C12 C13 C14 C15 -0.2(4) . . . . ?
C13 C14 C15 C16 -0.8(5) . . . . ?
C14 C15 C16 C11 0.2(4) . . . . ?
C16 C11 C12 C4 179.8(2) . . . . ?
C16 C11 C12 C13 -2.3(4) . . . . ?
C17 C4 C5 C6 110.4(2) . . . . ?
C17 C4 C12 C11 154.4(2) . . . . ?
C17 C4 C12 C13 -23.1(4) . . . . ?
C17 C5 C6 O2 -12.3(3) . . . . ?
C17 C5 C6 C7 167.2(2) . . . . ?
C19 C7 C8 C9 -0.8(4) . . . . ?
C21 O3 C20 O4 -0.6(4) . . . . ?
C21 O3 C20 C17 -178.1(2) . . . . ?
F24 C1 C2 O1 -60.3(4) . . . . ?
F25 C1 C2 O1 178.1(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
