# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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 
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# 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_cxy0823
_database_code_depnum_ccdc_archive 'CCDC 2102171'
loop_
_audit_author_name
_audit_author_address
'Xiao-Yong Chang'
;Southern University of Science and Technology
China
;
_audit_update_record             
;
2021-08-09 deposited with the CCDC.	2021-09-14 downloaded from the CCDC.
;
_audit_creation_date             2019-07-03
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H13 F6 N5 O'
_chemical_formula_sum            'C16 H13 F6 N5 O'
_chemical_formula_weight         405.31
_chemical_absolute_configuration ad
_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 0.0033 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      orthorhombic
_space_group_IT_number           18
_space_group_name_H-M_alt        'P 21 21 2'
_space_group_name_Hall           'P 2 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x+1/2, -y+1/2, -z'
'-x+1/2, y+1/2, -z'
'-x, -y, z'

_cell_length_a                   26.094(2)
_cell_length_b                   6.5624(5)
_cell_length_c                   9.4316(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1615.1(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9979
_cell_measurement_temperature    100
_cell_measurement_theta_max      27.44
_cell_measurement_theta_min      2.30
_shelx_estimated_absorpt_T_max   0.946
_shelx_estimated_absorpt_T_min   0.937
_exptl_absorpt_coefficient_mu    0.156
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.7076
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0718 before and 0.0541 after correction. The Ratio of minimum to maximum transmission is 0.9490. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.667
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             824
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.41
_exptl_crystal_size_min          0.36
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0334
_diffrn_reflns_av_unetI/netI     0.0305
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       33
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            13312
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.510
_diffrn_reflns_theta_min         2.159
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART APEX2 area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.713
_reflns_Friedel_fraction_full    0.994
_reflns_Friedel_fraction_max     0.992
_reflns_number_gt                3459
_reflns_number_total             3691
_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 (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.905
_refine_diff_density_min         -0.451
_refine_diff_density_rms         0.060
_refine_ls_abs_structure_details 
;
 Flack x determined using 1357 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.0(2)
_refine_ls_extinction_coef       0.018(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     261
_refine_ls_number_reflns         3691
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0475
_refine_ls_R_factor_gt           0.0436
_refine_ls_restrained_S_all      1.040
_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)+(0.0525P)²+1.3683P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1090
_refine_ls_wR_factor_ref         0.1117
_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
2. Uiso/Uaniso restraints and constraints
Uanis(F3) = Uanis(F3A)
Uanis(F7) = Uanis(F7A)
3. Others
 Sof(H8)=Sof(H16)=Sof(F3A)=Sof(F7A)=1-FVAR(1)
 Sof(F3)=Sof(F7)=Sof(H9)=Sof(H15)=FVAR(1)
4.a Riding coordinates:
 N2(H2)
4.b Ternary CH refined with riding coordinates:
 C4(H4), C5(H5)
4.c Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C11(H11A,H11B), C12(H12A,H12B), C14(H14A,H14B)
4.d Aromatic/amide H refined with riding coordinates:
 C8(H8), C9(H9), C15(H15), C16(H16)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_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 0.94977(9) 0.3604(5) 0.8146(3) 0.0500(7) Uani 1 1 d . . . . .
F2 F 0.45257(8) 0.3165(3) 0.5125(3) 0.0444(6) Uani 1 1 d . . . . .
F3 F 0.61997(9) 0.0976(4) 0.4316(3) 0.0242(5) Uani 0.746(3) 1 d . . P A 1
F4 F 0.90674(8) 0.2493(5) 0.9890(2) 0.0432(6) Uani 1 1 d . . . . .
F5 F 0.94220(10) 0.0400(4) 0.8473(3) 0.0541(8) Uani 1 1 d . . . . .
F7 F 0.46788(11) 0.2998(5) 0.7949(3) 0.0386(7) Uani 0.746(3) 1 d . . P A 1
O1 O 0.71213(8) 0.6455(3) 0.9778(2) 0.0224(5) Uani 1 1 d . . . . .
N1 N 0.83442(9) 0.3606(4) 0.7680(2) 0.0148(5) Uani 1 1 d . . . . .
N2 N 0.70721(9) 0.2910(4) 0.6178(2) 0.0143(5) Uani 1 1 d . . . . .
H2 H 0.684079 0.345942 0.561731 0.017 Uiso 1 1 d R . . . .
N3 N 0.74447(9) 0.5669(3) 0.7619(2) 0.0140(5) Uani 1 1 d . . . . .
N4 N 0.81194(9) 0.1234(4) 0.6151(3) 0.0162(5) Uani 1 1 d . . . . .
N5 N 0.85879(9) 0.0683(4) 0.6747(3) 0.0187(5) Uani 1 1 d . . . . .
C1 C 0.91752(12) 0.2128(5) 0.8538(3) 0.0242(7) Uani 1 1 d . . . . .
C2 C 0.87026(11) 0.2116(4) 0.7645(3) 0.0172(6) Uani 1 1 d . . . . .
C3 C 0.79837(10) 0.2965(4) 0.6733(3) 0.0133(5) Uani 1 1 d . . . . .
C4 C 0.75058(10) 0.4205(4) 0.6426(3) 0.0129(5) Uani 1 1 d . . . . .
H4 H 0.756885 0.500950 0.554281 0.015 Uiso 1 1 calc R . . . .
C5 C 0.68567(10) 0.2133(4) 0.7513(3) 0.0150(5) Uani 1 1 d . . . . .
H5 H 0.714136 0.145158 0.804158 0.018 Uiso 1 1 calc R . . . .
C6 C 0.64404(11) 0.0522(4) 0.7250(3) 0.0178(6) Uani 1 1 d . . . . .
H6A H 0.657584 -0.049073 0.656817 0.021 Uiso 1 1 calc R . . . .
H6B H 0.637381 -0.020023 0.815257 0.021 Uiso 1 1 calc R . . . .
C7 C 0.59363(11) 0.1319(4) 0.6687(3) 0.0172(6) Uani 1 1 d . . . . .
C8 C 0.58394(12) 0.1499(5) 0.5247(3) 0.0207(6) Uani 1 1 d . . . . .
H8 H 0.610674 0.117514 0.460119 0.025 Uiso 0.254(3) 1 calc R . P A 2
C9 C 0.53735(14) 0.2127(5) 0.4703(4) 0.0287(7) Uani 1 1 d . . . . .
H9 H 0.532269 0.222382 0.370779 0.034 Uiso 0.746(3) 1 calc R . P A 1
C10 C 0.49930(13) 0.2598(5) 0.5610(4) 0.0288(7) Uani 1 1 d . . . . .
C11 C 0.79094(11) 0.6852(4) 0.7880(3) 0.0163(6) Uani 1 1 d . . . . .
H11A H 0.783274 0.799900 0.852720 0.020 Uiso 1 1 calc R . . . .
H11B H 0.803945 0.741936 0.697617 0.020 Uiso 1 1 calc R . . . .
C12 C 0.83133(11) 0.5465(4) 0.8542(3) 0.0166(6) Uani 1 1 d . . . . .
H12A H 0.864973 0.616190 0.856036 0.020 Uiso 1 1 calc R . . . .
H12B H 0.821615 0.512040 0.952829 0.020 Uiso 1 1 calc R . . . .
C13 C 0.70976(11) 0.5452(4) 0.8681(3) 0.0152(5) Uani 1 1 d . . . . .
C14 C 0.66722(11) 0.3931(4) 0.8422(3) 0.0166(6) Uani 1 1 d . . . . .
H14A H 0.638388 0.461958 0.793673 0.020 Uiso 1 1 calc R . . . .
H14B H 0.654516 0.341193 0.934321 0.020 Uiso 1 1 calc R . . . .
C15 C 0.55384(12) 0.1869(5) 0.7586(3) 0.0228(6) Uani 1 1 d . . . . .
H15 H 0.558904 0.180870 0.858273 0.027 Uiso 0.746(3) 1 calc R . P A 1
C16 C 0.50693(12) 0.2504(5) 0.7060(4) 0.0281(7) Uani 1 1 d . . . . .
H16 H 0.480130 0.287276 0.769197 0.034 Uiso 0.254(3) 1 calc R . P A 2
F3A F 0.5623(3) 0.1670(12) 0.9012(7) 0.0242(5) Uani 0.254(3) 1 d . . P A 2
F7A F 0.5373(3) 0.2134(14) 0.3248(10) 0.0386(7) Uani 0.254(3) 1 d . . P A 2


_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 C1 1.335(4) . ?
F2 C10 1.355(4) . ?
F3 C8 1.331(4) . ?
F4 C1 1.327(4) . ?
F5 C1 1.306(4) . ?
F7 C16 1.359(4) . ?
O1 C13 1.228(4) . ?
N1 C2 1.353(4) . ?
N1 C3 1.364(4) . ?
N1 C12 1.468(3) . ?
N2 H2 0.8799 . ?
N2 C4 1.434(3) . ?
N2 C5 1.470(3) . ?
N3 C4 1.488(3) . ?
N3 C11 1.460(4) . ?
N3 C13 1.358(4) . ?
N4 N5 1.393(3) . ?
N4 C3 1.311(4) . ?
N5 C2 1.301(4) . ?
C1 C2 1.493(4) . ?
C3 C4 1.517(4) . ?
C4 H4 1.0000 . ?
C5 H5 1.0000 . ?
C5 C6 1.536(4) . ?
C5 C14 1.536(4) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C6 C7 1.512(4) . ?
C7 C8 1.387(4) . ?
C7 C15 1.388(4) . ?
C8 H8 0.9500 . ?
C8 C9 1.382(5) . ?
C9 H9 0.9500 . ?
C9 C10 1.346(5) . ?
C9 F7A 1.372(10) . ?
C10 C16 1.384(5) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 C12 1.526(4) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.513(4) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 H15 0.9500 . ?
C15 C16 1.385(5) . ?
C15 F3A 1.369(8) . ?
C16 H16 0.9500 . ?

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
C2 N1 C3 103.8(2) . . ?
C2 N1 C12 130.7(2) . . ?
C3 N1 C12 125.5(2) . . ?
C4 N2 H2 113.4 . . ?
C4 N2 C5 111.6(2) . . ?
C5 N2 H2 113.3 . . ?
C11 N3 C4 112.4(2) . . ?
C13 N3 C4 124.1(2) . . ?
C13 N3 C11 119.1(2) . . ?
C3 N4 N5 107.0(2) . . ?
C2 N5 N4 106.1(2) . . ?
F1 C1 C2 111.6(3) . . ?
F4 C1 F1 105.6(3) . . ?
F4 C1 C2 111.6(3) . . ?
F5 C1 F1 107.8(3) . . ?
F5 C1 F4 107.9(3) . . ?
F5 C1 C2 112.1(3) . . ?
N1 C2 C1 123.6(3) . . ?
N5 C2 N1 112.3(2) . . ?
N5 C2 C1 124.1(3) . . ?
N1 C3 C4 121.8(2) . . ?
N4 C3 N1 110.8(2) . . ?
N4 C3 C4 127.4(2) . . ?
N2 C4 N3 114.9(2) . . ?
N2 C4 C3 111.2(2) . . ?
N2 C4 H4 107.9 . . ?
N3 C4 C3 106.9(2) . . ?
N3 C4 H4 107.9 . . ?
C3 C4 H4 107.9 . . ?
N2 C5 H5 107.3 . . ?
N2 C5 C6 111.8(2) . . ?
N2 C5 C14 109.4(2) . . ?
C6 C5 H5 107.3 . . ?
C14 C5 H5 107.3 . . ?
C14 C5 C6 113.4(2) . . ?
C5 C6 H6A 108.3 . . ?
C5 C6 H6B 108.3 . . ?
H6A C6 H6B 107.4 . . ?
C7 C6 C5 115.7(2) . . ?
C7 C6 H6A 108.3 . . ?
C7 C6 H6B 108.3 . . ?
C8 C7 C6 122.1(3) . . ?
C8 C7 C15 116.1(3) . . ?
C15 C7 C6 121.8(3) . . ?
F3 C8 C7 119.7(3) . . ?
F3 C8 C9 117.0(3) . . ?
C7 C8 H8 118.3 . . ?
C9 C8 C7 123.3(3) . . ?
C9 C8 H8 118.3 . . ?
C8 C9 H9 120.6 . . ?
C10 C9 C8 118.8(3) . . ?
C10 C9 H9 120.6 . . ?
C10 C9 F7A 129.3(5) . . ?
F7A C9 C8 111.9(5) . . ?
F2 C10 C16 118.4(3) . . ?
C9 C10 F2 120.8(3) . . ?
C9 C10 C16 120.8(3) . . ?
N3 C11 H11A 109.9 . . ?
N3 C11 H11B 109.9 . . ?
N3 C11 C12 109.0(2) . . ?
H11A C11 H11B 108.3 . . ?
C12 C11 H11A 109.9 . . ?
C12 C11 H11B 109.9 . . ?
N1 C12 C11 107.8(2) . . ?
N1 C12 H12A 110.1 . . ?
N1 C12 H12B 110.1 . . ?
C11 C12 H12A 110.1 . . ?
C11 C12 H12B 110.1 . . ?
H12A C12 H12B 108.5 . . ?
O1 C13 N3 122.1(3) . . ?
O1 C13 C14 121.8(2) . . ?
N3 C13 C14 116.1(2) . . ?
C5 C14 H14A 109.3 . . ?
C5 C14 H14B 109.3 . . ?
C13 C14 C5 111.5(2) . . ?
C13 C14 H14A 109.3 . . ?
C13 C14 H14B 109.3 . . ?
H14A C14 H14B 108.0 . . ?
C7 C15 H15 119.3 . . ?
C16 C15 C7 121.4(3) . . ?
C16 C15 H15 119.3 . . ?
F3A C15 C7 117.0(4) . . ?
F3A C15 C16 121.6(4) . . ?
F7 C16 C10 119.4(3) . . ?
F7 C16 C15 120.9(3) . . ?
C10 C16 C15 119.6(3) . . ?
C10 C16 H16 120.2 . . ?
C15 C16 H16 120.2 . . ?

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
F1 C1 C2 N1 -68.4(4) . . . . ?
F1 C1 C2 N5 111.5(3) . . . . ?
F2 C10 C16 F7 -0.6(5) . . . . ?
F2 C10 C16 C15 178.0(3) . . . . ?
F3 C8 C9 C10 177.6(3) . . . . ?
F4 C1 C2 N1 49.5(4) . . . . ?
F4 C1 C2 N5 -130.6(3) . . . . ?
F5 C1 C2 N1 170.6(3) . . . . ?
F5 C1 C2 N5 -9.5(4) . . . . ?
O1 C13 C14 C5 -148.4(3) . . . . ?
N1 C3 C4 N2 -144.2(2) . . . . ?
N1 C3 C4 N3 -18.1(3) . . . . ?
N2 C5 C6 C7 -72.7(3) . . . . ?
N2 C5 C14 C13 -55.8(3) . . . . ?
N3 C11 C12 N1 49.2(3) . . . . ?
N3 C13 C14 C5 32.9(3) . . . . ?
N4 N5 C2 N1 -0.7(3) . . . . ?
N4 N5 C2 C1 179.4(3) . . . . ?
N4 C3 C4 N2 37.4(4) . . . . ?
N4 C3 C4 N3 163.5(2) . . . . ?
N5 N4 C3 N1 0.7(3) . . . . ?
N5 N4 C3 C4 179.2(2) . . . . ?
C2 N1 C3 N4 -1.1(3) . . . . ?
C2 N1 C3 C4 -179.7(2) . . . . ?
C2 N1 C12 C11 165.3(3) . . . . ?
C3 N1 C2 N5 1.1(3) . . . . ?
C3 N1 C2 C1 -179.0(3) . . . . ?
C3 N1 C12 C11 -17.5(4) . . . . ?
C3 N4 N5 C2 0.0(3) . . . . ?
C4 N2 C5 C6 -172.2(2) . . . . ?
C4 N2 C5 C14 61.4(3) . . . . ?
C4 N3 C11 C12 -71.8(3) . . . . ?
C4 N3 C13 O1 165.8(3) . . . . ?
C4 N3 C13 C14 -15.5(4) . . . . ?
C5 N2 C4 N3 -42.8(3) . . . . ?
C5 N2 C4 C3 78.8(3) . . . . ?
C5 C6 C7 C8 89.8(3) . . . . ?
C5 C6 C7 C15 -91.7(3) . . . . ?
C6 C5 C14 C13 178.7(2) . . . . ?
C6 C7 C8 F3 -0.6(4) . . . . ?
C6 C7 C8 C9 176.7(3) . . . . ?
C6 C7 C15 C16 -176.8(3) . . . . ?
C6 C7 C15 F3A 0.4(5) . . . . ?
C7 C8 C9 C10 0.3(5) . . . . ?
C7 C8 C9 F7A -178.7(5) . . . . ?
C7 C15 C16 F7 178.6(3) . . . . ?
C7 C15 C16 C10 -0.1(5) . . . . ?
C8 C7 C15 C16 1.7(4) . . . . ?
C8 C7 C15 F3A 178.9(4) . . . . ?
C8 C9 C10 F2 -178.1(3) . . . . ?
C8 C9 C10 C16 1.5(5) . . . . ?
C9 C10 C16 F7 179.7(3) . . . . ?
C9 C10 C16 C15 -1.6(5) . . . . ?
C11 N3 C4 N2 176.3(2) . . . . ?
C11 N3 C4 C3 52.4(3) . . . . ?
C11 N3 C13 O1 11.1(4) . . . . ?
C11 N3 C13 C14 -170.1(2) . . . . ?
C12 N1 C2 N5 178.8(3) . . . . ?
C12 N1 C2 C1 -1.3(5) . . . . ?
C12 N1 C3 N4 -178.9(2) . . . . ?
C12 N1 C3 C4 2.5(4) . . . . ?
C13 N3 C4 N2 20.1(4) . . . . ?
C13 N3 C4 C3 -103.8(3) . . . . ?
C13 N3 C11 C12 85.7(3) . . . . ?
C14 C5 C6 C7 51.5(3) . . . . ?
C15 C7 C8 F3 -179.1(3) . . . . ?
C15 C7 C8 C9 -1.9(4) . . . . ?
F3A C15 C16 C10 -177.2(5) . . . . ?
F7A C9 C10 F2 0.6(7) . . . . ?
F7A C9 C10 C16 -179.8(6) . . . . ?

_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_cxy0884_0m
_database_code_depnum_ccdc_archive 'CCDC 2102181'
loop_
_audit_author_name
_audit_author_address
'Xiao-Yong Chang'
;Southern University of Science and Technology
China
;
_audit_update_record             
;
2021-08-09 deposited with the CCDC.	2021-09-14 downloaded from the CCDC.
;
_audit_creation_date             2019-08-14
_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        ?
_chemical_formula_moiety         'C16 H13 F6 N5 O'
_chemical_formula_sum            'C16 H13 F6 N5 O'
_chemical_formula_weight         405.31
_chemical_absolute_configuration ad
_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 0.0033 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      triclinic
_space_group_IT_number           1
_space_group_name_H-M_alt        'P 1'
_space_group_name_Hall           'P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'

_cell_length_a                   4.6849(8)
_cell_length_b                   5.6677(10)
_cell_length_c                   15.258(3)
_cell_angle_alpha                98.838(6)
_cell_angle_beta                 91.269(6)
_cell_angle_gamma                93.319(6)
_cell_volume                     399.46(12)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    4848
_cell_measurement_temperature    100
_cell_measurement_theta_max      27.55
_cell_measurement_theta_min      2.70
_shelx_estimated_absorpt_T_max   0.963
_shelx_estimated_absorpt_T_min   0.957
_exptl_absorpt_coefficient_mu    0.158
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5257
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1568 before and 0.0786 after correction. The Ratio of minimum to maximum transmission is 0.7051. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.685
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             206
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.24
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0598
_diffrn_reflns_av_unetI/netI     0.0752
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            6666
_diffrn_reflns_point_group_measured_fraction_full 0.956
_diffrn_reflns_point_group_measured_fraction_max 0.937
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.560
_diffrn_reflns_theta_min         2.703
_diffrn_ambient_temperature      100.01
_diffrn_detector                 'Bruker PHOTON 100 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CMOS area detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'BrukerD8 venture microsource'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.879
_reflns_Friedel_fraction_full    0.914
_reflns_Friedel_fraction_max     0.877
_reflns_number_gt                3100
_reflns_number_total             3455
_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 (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_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         0.220
_refine_diff_density_min         -0.202
_refine_diff_density_rms         0.052
_refine_ls_abs_structure_details 
;
 Flack x determined using 1279 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.3(5)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         3455
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0490
_refine_ls_R_factor_gt           0.0377
_refine_ls_restrained_S_all      1.030
_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)+(0.0273P)²+0.0730P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0906
_refine_ls_wR_factor_ref         0.0949
_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
2.a Riding coordinates:
 N1(H1)
2.b Ternary CH refined with riding coordinates:
 C6(H6), C7(H7)
2.c Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B), C14(H14A,H14B), C17(H17A,H17B), C18(H18A,H18B)
2.d Aromatic/amide H refined with riding coordinates:
 C3(H3), C15(H15)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_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 0.7430(5) 0.7246(4) 0.96953(14) 0.0378(6) Uani 1 1 d . . . . .
F2 F 0.1112(4) 0.8230(3) 0.73604(14) 0.0276(5) Uani 1 1 d . . . . .
F3 F 0.8858(5) 0.3033(4) 0.87886(14) 0.0323(5) Uani 1 1 d . . . . .
F4 F 0.1364(4) 0.1288(3) 0.03025(13) 0.0282(5) Uani 1 1 d . . . . .
F5 F 0.5659(4) 0.2868(4) 0.04890(13) 0.0296(5) Uani 1 1 d . . . . .
F6 F 0.2106(5) 0.5059(3) 0.07812(14) 0.0303(5) Uani 1 1 d . . . . .
O1 O 0.8651(5) 0.9349(4) 0.48972(15) 0.0180(5) Uani 1 1 d . . . . .
N1 N 0.3212(5) 0.3493(4) 0.47001(16) 0.0141(5) Uani 1 1 d . . . . .
H1 H 0.224611 0.196509 0.468214 0.017 Uiso 1 1 d R . . . .
N2 N 0.4738(5) 0.3722(4) 0.24242(16) 0.0137(5) Uani 1 1 d . . . . .
N3 N 0.6674(5) 0.5958(4) 0.40670(17) 0.0145(5) Uani 1 1 d . . . . .
N4 N 0.1623(6) 0.0635(4) 0.20328(18) 0.0192(6) Uani 1 1 d . . . . .
N5 N 0.2300(6) 0.0806(4) 0.29292(18) 0.0184(5) Uani 1 1 d . . . . .
C1 C 0.6188(8) 0.6451(6) 0.8896(2) 0.0253(7) Uani 1 1 d . . . . .
C2 C 0.6918(7) 0.4303(6) 0.8429(2) 0.0230(7) Uani 1 1 d . . . . .
C3 C 0.5705(7) 0.3445(6) 0.7606(2) 0.0194(6) Uani 1 1 d . . . . .
H3 H 0.623277 0.195895 0.729474 0.023 Uiso 1 1 calc R . . . .
C4 C 0.3702(7) 0.4740(5) 0.7222(2) 0.0164(6) Uani 1 1 d . . . . .
C5 C 0.2417(7) 0.3878(5) 0.6303(2) 0.0171(6) Uani 1 1 d . . . . .
H5A H 0.067982 0.474241 0.621817 0.021 Uiso 1 1 calc R . . . .
H5B H 0.184154 0.215146 0.624561 0.021 Uiso 1 1 calc R . . . .
C6 C 0.4533(6) 0.4280(5) 0.55844(19) 0.0139(6) Uani 1 1 d . . . . .
H6 H 0.625979 0.336060 0.565579 0.017 Uiso 1 1 calc R . . . .
C7 C 0.5419(6) 0.3504(5) 0.40506(19) 0.0128(5) Uani 1 1 d . . . . .
H7 H 0.694426 0.243584 0.418370 0.015 Uiso 1 1 calc R . . . .
C8 C 0.4148(6) 0.2650(5) 0.31401(19) 0.0132(6) Uani 1 1 d . . . . .
C9 C 0.3096(6) 0.2392(5) 0.1755(2) 0.0153(6) Uani 1 1 d . . . . .
C10 C 0.3049(7) 0.2902(6) 0.0821(2) 0.0196(6) Uani 1 1 d . . . . .
C13 C 0.7106(6) 0.7499(5) 0.48409(19) 0.0144(6) Uani 1 1 d . . . . .
C14 C 0.5443(7) 0.6923(5) 0.5626(2) 0.0157(6) Uani 1 1 d . . . . .
H14A H 0.371100 0.785000 0.567007 0.019 Uiso 1 1 calc R . . . .
H14B H 0.663084 0.745493 0.617334 0.019 Uiso 1 1 calc R . . . .
C15 C 0.4204(8) 0.7777(6) 0.8546(2) 0.0252(7) Uani 1 1 d . . . . .
H15 H 0.366214 0.924848 0.886595 0.030 Uiso 1 1 calc R . . . .
C16 C 0.3032(7) 0.6895(5) 0.7716(2) 0.0201(6) Uani 1 1 d . . . . .
C17 C 0.8389(7) 0.6264(5) 0.3303(2) 0.0166(6) Uani 1 1 d . . . . .
H17A H 0.986004 0.506845 0.323572 0.020 Uiso 1 1 calc R . . . .
H17B H 0.938104 0.787690 0.339973 0.020 Uiso 1 1 calc R . . . .
C18 C 0.6525(7) 0.5962(5) 0.2463(2) 0.0167(6) Uani 1 1 d . . . . .
H18A H 0.530304 0.733334 0.247324 0.020 Uiso 1 1 calc R . . . .
H18B H 0.773157 0.588634 0.193606 0.020 Uiso 1 1 calc R . . . .


_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 C1 1.341(4) . ?
F2 C16 1.363(4) . ?
F3 C2 1.349(4) . ?
F4 C10 1.324(4) . ?
F5 C10 1.334(4) . ?
F6 C10 1.333(4) . ?
O1 C13 1.230(4) . ?
N1 H1 0.9500 . ?
N1 C6 1.466(4) . ?
N1 C7 1.448(4) . ?
N2 C8 1.356(4) . ?
N2 C9 1.365(4) . ?
N2 C18 1.472(4) . ?
N3 C7 1.475(3) . ?
N3 C13 1.360(4) . ?
N3 C17 1.457(4) . ?
N4 N5 1.385(4) . ?
N4 C9 1.308(4) . ?
N5 C8 1.313(4) . ?
C1 C2 1.378(5) . ?
C1 C15 1.377(5) . ?
C2 C3 1.373(4) . ?
C3 H3 0.9500 . ?
C3 C4 1.396(4) . ?
C4 C5 1.511(4) . ?
C4 C16 1.389(4) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C5 C6 1.528(4) . ?
C6 H6 1.0000 . ?
C6 C14 1.525(4) . ?
C7 H7 1.0000 . ?
C7 C8 1.497(4) . ?
C9 C10 1.497(4) . ?
C13 C14 1.510(4) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 H15 0.9500 . ?
C15 C16 1.378(5) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C17 C18 1.516(4) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?

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
C6 N1 H1 109.5 . . ?
C7 N1 H1 112.9 . . ?
C7 N1 C6 108.5(2) . . ?
C8 N2 C9 103.7(2) . . ?
C8 N2 C18 124.0(2) . . ?
C9 N2 C18 131.9(2) . . ?
C13 N3 C7 121.4(2) . . ?
C13 N3 C17 120.2(2) . . ?
C17 N3 C7 114.1(2) . . ?
C9 N4 N5 106.2(2) . . ?
C8 N5 N4 107.3(2) . . ?
F1 C1 C2 119.5(3) . . ?
F1 C1 C15 120.1(3) . . ?
C15 C1 C2 120.4(3) . . ?
F3 C2 C1 119.2(3) . . ?
F3 C2 C3 119.8(3) . . ?
C3 C2 C1 121.0(3) . . ?
C2 C3 H3 119.7 . . ?
C2 C3 C4 120.5(3) . . ?
C4 C3 H3 119.7 . . ?
C3 C4 C5 121.5(3) . . ?
C16 C4 C3 116.5(3) . . ?
C16 C4 C5 121.9(3) . . ?
C4 C5 H5A 109.3 . . ?
C4 C5 H5B 109.3 . . ?
C4 C5 C6 111.5(3) . . ?
H5A C5 H5B 108.0 . . ?
C6 C5 H5A 109.3 . . ?
C6 C5 H5B 109.3 . . ?
N1 C6 C5 110.5(2) . . ?
N1 C6 H6 109.5 . . ?
N1 C6 C14 106.2(2) . . ?
C5 C6 H6 109.5 . . ?
C14 C6 C5 111.7(2) . . ?
C14 C6 H6 109.5 . . ?
N1 C7 N3 110.0(2) . . ?
N1 C7 H7 109.7 . . ?
N1 C7 C8 109.8(2) . . ?
N3 C7 H7 109.7 . . ?
N3 C7 C8 107.8(2) . . ?
C8 C7 H7 109.7 . . ?
N2 C8 C7 123.8(3) . . ?
N5 C8 N2 111.1(3) . . ?
N5 C8 C7 125.1(3) . . ?
N2 C9 C10 123.3(3) . . ?
N4 C9 N2 111.7(3) . . ?
N4 C9 C10 125.0(3) . . ?
F4 C10 F5 108.0(3) . . ?
F4 C10 F6 108.4(3) . . ?
F4 C10 C9 110.7(3) . . ?
F5 C10 C9 111.3(3) . . ?
F6 C10 F5 107.3(3) . . ?
F6 C10 C9 111.0(2) . . ?
O1 C13 N3 122.3(3) . . ?
O1 C13 C14 120.7(3) . . ?
N3 C13 C14 116.9(2) . . ?
C6 C14 H14A 108.7 . . ?
C6 C14 H14B 108.7 . . ?
C13 C14 C6 114.4(2) . . ?
C13 C14 H14A 108.7 . . ?
C13 C14 H14B 108.7 . . ?
H14A C14 H14B 107.6 . . ?
C1 C15 H15 121.2 . . ?
C1 C15 C16 117.6(3) . . ?
C16 C15 H15 121.2 . . ?
F2 C16 C4 118.4(3) . . ?
F2 C16 C15 117.7(3) . . ?
C15 C16 C4 123.9(3) . . ?
N3 C17 H17A 109.5 . . ?
N3 C17 H17B 109.5 . . ?
N3 C17 C18 110.8(2) . . ?
H17A C17 H17B 108.1 . . ?
C18 C17 H17A 109.5 . . ?
C18 C17 H17B 109.5 . . ?
N2 C18 C17 107.6(2) . . ?
N2 C18 H18A 110.2 . . ?
N2 C18 H18B 110.2 . . ?
C17 C18 H18A 110.2 . . ?
C17 C18 H18B 110.2 . . ?
H18A C18 H18B 108.5 . . ?

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
F1 C1 C2 F3 0.4(5) . . . . ?
F1 C1 C2 C3 -179.5(3) . . . . ?
F1 C1 C15 C16 178.9(3) . . . . ?
F3 C2 C3 C4 -179.8(3) . . . . ?
O1 C13 C14 C6 -158.8(3) . . . . ?
N1 C6 C14 C13 -49.0(3) . . . . ?
N1 C7 C8 N2 135.3(3) . . . . ?
N1 C7 C8 N5 -43.6(4) . . . . ?
N2 C9 C10 F4 177.6(3) . . . . ?
N2 C9 C10 F5 57.5(4) . . . . ?
N2 C9 C10 F6 -61.9(4) . . . . ?
N3 C7 C8 N2 15.4(4) . . . . ?
N3 C7 C8 N5 -163.5(3) . . . . ?
N3 C13 C14 C6 25.0(4) . . . . ?
N3 C17 C18 N2 -49.9(3) . . . . ?
N4 N5 C8 N2 0.0(3) . . . . ?
N4 N5 C8 C7 179.1(3) . . . . ?
N4 C9 C10 F4 -1.7(4) . . . . ?
N4 C9 C10 F5 -121.8(3) . . . . ?
N4 C9 C10 F6 118.8(3) . . . . ?
N5 N4 C9 N2 0.3(3) . . . . ?
N5 N4 C9 C10 179.7(3) . . . . ?
C1 C2 C3 C4 0.2(5) . . . . ?
C1 C15 C16 F2 -178.7(3) . . . . ?
C1 C15 C16 C4 1.1(5) . . . . ?
C2 C1 C15 C16 -1.0(5) . . . . ?
C2 C3 C4 C5 177.8(3) . . . . ?
C2 C3 C4 C16 -0.1(4) . . . . ?
C3 C4 C5 C6 -75.4(3) . . . . ?
C3 C4 C16 F2 179.2(3) . . . . ?
C3 C4 C16 C15 -0.5(4) . . . . ?
C4 C5 C6 N1 -178.4(2) . . . . ?
C4 C5 C6 C14 -60.4(3) . . . . ?
C5 C4 C16 F2 1.3(4) . . . . ?
C5 C4 C16 C15 -178.4(3) . . . . ?
C5 C6 C14 C13 -169.6(2) . . . . ?
C6 N1 C7 N3 -62.8(3) . . . . ?
C6 N1 C7 C8 178.6(2) . . . . ?
C7 N1 C6 C5 -169.9(2) . . . . ?
C7 N1 C6 C14 68.8(3) . . . . ?
C7 N3 C13 O1 164.9(3) . . . . ?
C7 N3 C13 C14 -18.9(4) . . . . ?
C7 N3 C17 C18 67.2(3) . . . . ?
C8 N2 C9 N4 -0.3(3) . . . . ?
C8 N2 C9 C10 -179.7(3) . . . . ?
C8 N2 C18 C17 21.3(4) . . . . ?
C9 N2 C8 N5 0.2(3) . . . . ?
C9 N2 C8 C7 -178.9(3) . . . . ?
C9 N2 C18 C17 -166.5(3) . . . . ?
C9 N4 N5 C8 -0.2(3) . . . . ?
C13 N3 C7 N1 37.6(4) . . . . ?
C13 N3 C7 C8 157.3(3) . . . . ?
C13 N3 C17 C18 -135.7(3) . . . . ?
C15 C1 C2 F3 -179.7(3) . . . . ?
C15 C1 C2 C3 0.4(5) . . . . ?
C16 C4 C5 C6 102.3(3) . . . . ?
C17 N3 C7 N1 -165.7(2) . . . . ?
C17 N3 C7 C8 -45.9(3) . . . . ?
C17 N3 C13 O1 9.5(4) . . . . ?
C17 N3 C13 C14 -174.3(2) . . . . ?
C18 N2 C8 N5 174.2(3) . . . . ?
C18 N2 C8 C7 -4.9(4) . . . . ?
C18 N2 C9 N4 -173.6(3) . . . . ?
C18 N2 C9 C10 7.0(5) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
