# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_20220457
_database_code_depnum_ccdc_archive 'CCDC 2201061'
loop_
_audit_author_name
_audit_author_address
danjingwu
;Zhengzhou University
China
;
_audit_update_record             
;
2022-08-12 deposited with the CCDC.	2023-03-03 downloaded from the CCDC.
;
_audit_creation_date             2022-04-09
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H15 F2 N O2 S'
_chemical_formula_sum            'C17 H15 F2 N O2 S'
_chemical_formula_weight         335.36
_chemical_melting_point          ?
_chemical_oxdiff_formula         C30H3O3N1
_chemical_oxdiff_usercomment     r
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'
S S 0.3331 0.5567 '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                   8.2517(11)
_cell_length_b                   9.8720(12)
_cell_length_c                   10.8789(13)
_cell_angle_alpha                110.880(11)
_cell_angle_beta                 93.478(10)
_cell_angle_gamma                100.696(11)
_cell_volume                     805.82(18)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1303
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      69.3230
_cell_measurement_theta_min      4.3780
_shelx_estimated_absorpt_T_max   0.821
_shelx_estimated_absorpt_T_min   0.776
_exptl_absorpt_coefficient_mu    2.056
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.93551
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.382
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             348
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0278
_diffrn_reflns_av_unetI/netI     0.0421
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            5655
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.049
_diffrn_reflns_theta_max         67.049
_diffrn_reflns_theta_min         4.392
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2312
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -56.00  37.00   1.00    1.00    --  -33.50  37.00-150.00   93
  2  ω    -56.00  37.00   1.00    1.00    --  -33.50  37.00   0.00   93
  3  ω   -104.00 -11.00   1.00    1.00    --  -33.50 -37.00  30.00   93
  4  ω     57.00 110.00   1.00    1.00    --   36.47 178.00  60.00   53
  5  ω     -4.00  77.00   1.00    1.00    --   36.47 -99.00 -90.00   81
  6  ω     18.00 105.00   1.00    1.00    --   36.47  57.00 150.00   87
  7  ω     14.00 107.00   1.00    1.00    --   36.47  37.00-120.00   93
  8  ω     -4.00  77.00   1.00    1.00    --   36.47 -99.00  60.00   81
  9  ω     -4.00  77.00   1.00    1.00    --   36.47 -99.00 150.00   81
 10  ω     40.00 128.00   1.00    3.00    --  108.00 -61.00 150.00   88
 11  ω     38.00 128.00   1.00    3.00    --  108.00 -45.00   0.00   90
 12  ω     82.00 178.00   1.00    3.00    --  108.00  30.00 -30.00   96
 13  ω     88.00 178.00   1.00    3.00    --  108.00  45.00 150.00   90
 14  ω    145.00 172.00   1.00    3.00    --  108.00  15.00 -90.00   27
 15  ω     37.00 144.00   1.00    3.00    --  108.00 -15.00 120.00  107
 16  ω     59.00  99.00   1.00    3.00    --  108.00 178.00 150.00   40
 17  ω     62.00 149.00   1.00    3.00    --  108.00 178.00 120.00   87
 18  ω     76.00 102.00   1.00    3.00    --  108.00-111.00-180.00   26
 19  ω     37.00  63.00   1.00    3.00    --  108.00-111.00-180.00   26
 20  ω     73.00 112.00   1.00    3.00    --  108.00-111.00 -90.00   39
 21  ω     52.00 128.00   1.00    3.00    --  108.00 -61.00-120.00   76
 22  ω     52.00 106.00   1.00    3.00    --  108.00 -94.00  60.00   54
 23  ω     91.00 133.00   1.00    3.00    --  108.00 -77.00  60.00   42
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0935994000
_diffrn_orient_matrix_UB_12      0.0858059000
_diffrn_orient_matrix_UB_13      -0.0776604000
_diffrn_orient_matrix_UB_21      -0.1632086000
_diffrn_orient_matrix_UB_22      0.0373552000
_diffrn_orient_matrix_UB_23      -0.0406200000
_diffrn_orient_matrix_UB_31      0.0374231000
_diffrn_orient_matrix_UB_32      0.1434538000
_diffrn_orient_matrix_UB_33      0.1254818000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2161
_reflns_number_total             2869
_reflns_odcompleteness_completeness 99.72
_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 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.194
_refine_diff_density_min         -0.341
_refine_diff_density_rms         0.045
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     210
_refine_ls_number_reflns         2869
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0671
_refine_ls_R_factor_gt           0.0494
_refine_ls_restrained_S_all      1.042
_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)+(0.0683P)²+0.1296P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1286
_refine_ls_wR_factor_ref         0.1457
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C16(H16)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C10(H10), C11(H11), C13(H13), C15(H15)
2.c Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C17(H17A,H17B,H17C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.23311(8) 0.32919(8) 0.23172(9) 0.0626(3) Uani 1 1 d . . . . .
F1 F 0.6769(3) 0.1454(2) 0.5803(2) 0.0999(8) Uani 1 1 d . . . . .
F2 F 0.8281(3) 0.0627(3) 0.4269(3) 0.1217(10) Uani 1 1 d . . . . .
O1 O 0.1715(3) 0.2664(3) 0.0936(3) 0.0894(8) Uani 1 1 d . . . . .
O2 O 0.1562(3) 0.4359(3) 0.3209(3) 0.0933(9) Uani 1 1 d . . . . .
N1 N 0.2252(3) 0.1951(3) 0.2848(2) 0.0557(6) Uani 1 1 d . . . . .
C1 C 0.5231(3) -0.0366(3) 0.1418(3) 0.0524(6) Uani 1 1 d . . . . .
H1 H 0.6373 -0.0301 0.1458 0.063 Uiso 1 1 calc R . . . .
C2 C 0.4130(4) -0.1686(3) 0.0613(3) 0.0586(7) Uani 1 1 d . . . . .
H2 H 0.4540 -0.2508 0.0137 0.070 Uiso 1 1 calc R . . . .
C3 C 0.2443(4) -0.1781(3) 0.0518(3) 0.0651(8) Uani 1 1 d . . . . .
H3 H 0.1720 -0.2660 -0.0037 0.078 Uiso 1 1 calc R . . . .
C4 C 0.1814(4) -0.0590(3) 0.1236(3) 0.0592(7) Uani 1 1 d . . . . .
H4 H 0.0670 -0.0658 0.1173 0.071 Uiso 1 1 calc R . . . .
C5 C 0.2905(3) 0.0719(3) 0.2058(3) 0.0491(6) Uani 1 1 d . . . . .
C6 C 0.4625(3) 0.0855(3) 0.2162(2) 0.0449(6) Uani 1 1 d . . . . .
C7 C 0.5765(3) 0.2281(3) 0.3054(3) 0.0456(6) Uani 1 1 d . . . . .
C8 C 0.5833(3) 0.3651(3) 0.2738(2) 0.0442(5) Uani 1 1 d . . . . .
C9 C 0.4447(3) 0.4154(3) 0.2424(3) 0.0498(6) Uani 1 1 d . . . . .
C10 C 0.4658(4) 0.5431(3) 0.2120(3) 0.0646(8) Uani 1 1 d . . . . .
H10 H 0.3731 0.5776 0.1940 0.078 Uiso 1 1 calc R . . . .
C11 C 0.6216(4) 0.6181(3) 0.2083(3) 0.0677(8) Uani 1 1 d . . . . .
H11 H 0.6337 0.7028 0.1876 0.081 Uiso 1 1 calc R . . . .
C12 C 0.7615(3) 0.5690(3) 0.2352(3) 0.0566(7) Uani 1 1 d . . . . .
C13 C 0.7396(3) 0.4445(3) 0.2691(3) 0.0487(6) Uani 1 1 d . . . . .
H13 H 0.8334 0.4128 0.2896 0.058 Uiso 1 1 calc R . . . .
C14 C 0.9316(4) 0.6489(4) 0.2259(4) 0.0831(11) Uani 1 1 d . . . . .
H14A H 1.0145 0.6045 0.2526 0.125 Uiso 1 1 calc GR . . . .
H14B H 0.9509 0.7517 0.2833 0.125 Uiso 1 1 calc GR . . . .
H14C H 0.9380 0.6414 0.1360 0.125 Uiso 1 1 calc GR . . . .
C15 C 0.6782(3) 0.2341(3) 0.4083(3) 0.0561(7) Uani 1 1 d . . . . .
H15 H 0.7505 0.3244 0.4585 0.067 Uiso 1 1 calc R . . . .
C16 C 0.6828(4) 0.1052(4) 0.4471(3) 0.0678(8) Uani 1 1 d . . . . .
H16 H 0.5892 0.0222 0.3970 0.081 Uiso 1 1 calc R . . . .
C17 C 0.2244(5) 0.2230(4) 0.4271(4) 0.0797(10) Uani 1 1 d . . . . .
H17A H 0.3368 0.2556 0.4715 0.120 Uiso 1 1 calc GR . . . .
H17B H 0.1721 0.1330 0.4374 0.120 Uiso 1 1 calc GR . . . .
H17C H 0.1638 0.2985 0.4652 0.120 Uiso 1 1 calc GR . . . .


_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
S1 O1 1.424(3) . ?
S1 O2 1.431(2) . ?
S1 N1 1.614(2) . ?
S1 C9 1.771(3) . ?
F1 C16 1.365(4) . ?
F2 C16 1.348(4) . ?
N1 C5 1.436(3) . ?
N1 C17 1.474(4) . ?
C1 H1 0.9300 . ?
C1 C2 1.393(4) . ?
C1 C6 1.391(4) . ?
C2 H2 0.9300 . ?
C2 C3 1.372(5) . ?
C3 H3 0.9300 . ?
C3 C4 1.372(4) . ?
C4 H4 0.9300 . ?
C4 C5 1.388(4) . ?
C5 C6 1.394(4) . ?
C6 C7 1.494(3) . ?
C7 C8 1.502(3) . ?
C7 C15 1.335(4) . ?
C8 C9 1.398(4) . ?
C8 C13 1.394(3) . ?
C9 C10 1.398(4) . ?
C10 H10 0.9300 . ?
C10 C11 1.370(4) . ?
C11 H11 0.9300 . ?
C11 C12 1.386(4) . ?
C12 C13 1.388(4) . ?
C12 C14 1.505(4) . ?
C13 H13 0.9300 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 H15 0.9300 . ?
C15 C16 1.483(4) . ?
C16 H16 0.9800 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 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
O1 S1 O2 119.74(18) . . ?
O1 S1 N1 108.14(13) . . ?
O1 S1 C9 105.29(15) . . ?
O2 S1 N1 106.82(15) . . ?
O2 S1 C9 107.83(13) . . ?
N1 S1 C9 108.66(12) . . ?
C5 N1 S1 116.08(18) . . ?
C5 N1 C17 118.0(2) . . ?
C17 N1 S1 120.6(2) . . ?
C2 C1 H1 119.9 . . ?
C6 C1 H1 119.9 . . ?
C6 C1 C2 120.1(3) . . ?
C1 C2 H2 119.8 . . ?
C3 C2 C1 120.4(3) . . ?
C3 C2 H2 119.8 . . ?
C2 C3 H3 119.7 . . ?
C4 C3 C2 120.6(3) . . ?
C4 C3 H3 119.7 . . ?
C3 C4 H4 120.4 . . ?
C3 C4 C5 119.2(3) . . ?
C5 C4 H4 120.4 . . ?
C4 C5 N1 119.4(2) . . ?
C4 C5 C6 121.5(3) . . ?
C6 C5 N1 119.0(2) . . ?
C1 C6 C5 118.1(2) . . ?
C1 C6 C7 121.7(2) . . ?
C5 C6 C7 120.2(2) . . ?
C6 C7 C8 119.1(2) . . ?
C15 C7 C6 121.3(2) . . ?
C15 C7 C8 119.5(2) . . ?
C9 C8 C7 125.1(2) . . ?
C13 C8 C7 117.5(2) . . ?
C13 C8 C9 117.3(2) . . ?
C8 C9 S1 126.33(19) . . ?
C10 C9 S1 113.4(2) . . ?
C10 C9 C8 120.2(2) . . ?
C9 C10 H10 119.6 . . ?
C11 C10 C9 120.7(3) . . ?
C11 C10 H10 119.6 . . ?
C10 C11 H11 119.7 . . ?
C10 C11 C12 120.6(2) . . ?
C12 C11 H11 119.7 . . ?
C11 C12 C13 118.3(3) . . ?
C11 C12 C14 120.2(3) . . ?
C13 C12 C14 121.6(3) . . ?
C8 C13 H13 118.6 . . ?
C12 C13 C8 122.8(2) . . ?
C12 C13 H13 118.6 . . ?
C12 C14 H14A 109.5 . . ?
C12 C14 H14B 109.5 . . ?
C12 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C7 C15 H15 118.1 . . ?
C7 C15 C16 123.8(3) . . ?
C16 C15 H15 118.1 . . ?
F1 C16 C15 109.8(3) . . ?
F1 C16 H16 110.2 . . ?
F2 C16 F1 105.6(3) . . ?
F2 C16 C15 110.7(3) . . ?
F2 C16 H16 110.2 . . ?
C15 C16 H16 110.2 . . ?
N1 C17 H17A 109.5 . . ?
N1 C17 H17B 109.5 . . ?
N1 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 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
S1 N1 C5 C4 -103.3(2) . . . . ?
S1 N1 C5 C6 78.2(3) . . . . ?
S1 C9 C10 C11 -176.3(3) . . . . ?
O1 S1 N1 C5 47.5(2) . . . . ?
O1 S1 N1 C17 -158.8(2) . . . . ?
O1 S1 C9 C8 -107.5(3) . . . . ?
O1 S1 C9 C10 70.7(3) . . . . ?
O2 S1 N1 C5 177.6(2) . . . . ?
O2 S1 N1 C17 -28.7(3) . . . . ?
O2 S1 C9 C8 123.5(3) . . . . ?
O2 S1 C9 C10 -58.3(3) . . . . ?
N1 S1 C9 C8 8.1(3) . . . . ?
N1 S1 C9 C10 -173.7(2) . . . . ?
N1 C5 C6 C1 178.1(2) . . . . ?
N1 C5 C6 C7 -1.7(4) . . . . ?
C1 C2 C3 C4 -1.5(4) . . . . ?
C1 C6 C7 C8 114.6(3) . . . . ?
C1 C6 C7 C15 -61.9(4) . . . . ?
C2 C1 C6 C5 -0.9(4) . . . . ?
C2 C1 C6 C7 178.9(2) . . . . ?
C2 C3 C4 C5 0.3(4) . . . . ?
C3 C4 C5 N1 -177.8(3) . . . . ?
C3 C4 C5 C6 0.6(4) . . . . ?
C4 C5 C6 C1 -0.3(4) . . . . ?
C4 C5 C6 C7 179.9(2) . . . . ?
C5 C6 C7 C8 -65.5(3) . . . . ?
C5 C6 C7 C15 118.0(3) . . . . ?
C6 C1 C2 C3 1.8(4) . . . . ?
C6 C7 C8 C9 48.2(4) . . . . ?
C6 C7 C8 C13 -128.6(3) . . . . ?
C6 C7 C15 C16 -2.9(5) . . . . ?
C7 C8 C9 S1 -0.6(4) . . . . ?
C7 C8 C9 C10 -178.7(3) . . . . ?
C7 C8 C13 C12 177.1(3) . . . . ?
C7 C15 C16 F1 -131.3(3) . . . . ?
C7 C15 C16 F2 112.6(4) . . . . ?
C8 C7 C15 C16 -179.4(3) . . . . ?
C8 C9 C10 C11 2.0(5) . . . . ?
C9 S1 N1 C5 -66.3(2) . . . . ?
C9 S1 N1 C17 87.4(2) . . . . ?
C9 C8 C13 C12 0.0(4) . . . . ?
C9 C10 C11 C12 -0.2(5) . . . . ?
C10 C11 C12 C13 -1.6(5) . . . . ?
C10 C11 C12 C14 177.7(3) . . . . ?
C11 C12 C13 C8 1.7(5) . . . . ?
C13 C8 C9 S1 176.2(2) . . . . ?
C13 C8 C9 C10 -1.9(4) . . . . ?
C14 C12 C13 C8 -177.6(3) . . . . ?
C15 C7 C8 C9 -135.3(3) . . . . ?
C15 C7 C8 C13 47.9(4) . . . . ?
C17 N1 C5 C4 102.3(3) . . . . ?
C17 N1 C5 C6 -76.2(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.141
_oxdiff_exptl_absorpt_empirical_full_min 0.912
####################################################################### 
# 
# 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_20220693
_database_code_depnum_ccdc_archive 'CCDC 2201068'
loop_
_audit_author_name
_audit_author_address
danjingliu
;Zhengzhou University
China
;
_audit_update_record             
;
2022-08-12 deposited with the CCDC.	2023-03-03 downloaded from the CCDC.
;
_audit_creation_date             2022-06-16
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H12 F5 N O'
_chemical_formula_sum            'C18 H12 F5 N O'
_chemical_formula_weight         353.29
_chemical_melting_point          ?
_chemical_oxdiff_formula         C30H3O3N3
_chemical_oxdiff_usercomment     r
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                   8.5281(4)
_cell_length_b                   9.1272(5)
_cell_length_c                   19.9962(11)
_cell_angle_alpha                90
_cell_angle_beta                 90.685(5)
_cell_angle_gamma                90
_cell_volume                     1556.34(15)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1542
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      69.4050
_cell_measurement_theta_min      4.3920
_shelx_estimated_absorpt_T_max   0.911
_shelx_estimated_absorpt_T_min   0.852
_exptl_absorpt_coefficient_mu    1.180
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.81215
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            gray
_exptl_crystal_colour_primary    gray
_exptl_crystal_density_diffrn    1.508
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             720
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0331
_diffrn_reflns_av_unetI/netI     0.0460
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            5681
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.066
_diffrn_reflns_theta_max         67.066
_diffrn_reflns_theta_min         5.327
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2312
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -96.00  -5.00   1.00    3.50    --  -33.50 137.00 167.00   91
  2  ω     37.00  84.00   1.00    3.50    --   36.54  37.00-150.00   47
  3  ω    -31.00  54.00   1.00    3.50    --   36.54 -57.00 -60.00   85
  4  ω     11.00  53.00   1.00    3.50    --   36.54 -77.00  60.00   42
  5  ω    -32.00   6.00   1.00    3.50    --   36.54 -77.00  60.00   38
  6  ω    -17.00  51.00   1.00    3.50    --   36.54 -77.00 -90.00   68
  7  ω     -9.00  61.00   1.00    3.50    --   36.54 -77.00-180.00   70
  8  ω    103.00 177.00   1.00   13.00    --  108.00  45.00-120.00   74
  9  ω     41.00 103.00   1.00   13.00    --  108.00-111.00  60.00   62
 10  ω     47.00  85.00   1.00   13.00    --  108.00 -15.00-120.00   38
 11  ω     39.00 134.00   1.00   13.00    --  108.00 -30.00  60.00   95
 12  ω     85.00 122.00   1.00   13.00    --  108.00 -30.00-180.00   37
 13  ω     76.00 109.00   1.00   13.00    --  108.00 -94.00 150.00   33
 14  ω     96.00 153.00   1.00   13.00    --  108.00 -15.00-120.00   57
 15  ω     40.00 137.00   1.00   13.00    --  108.00 -77.00-120.00   97
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1202113000
_diffrn_orient_matrix_UB_12      -0.0253891000
_diffrn_orient_matrix_UB_13      0.0556801000
_diffrn_orient_matrix_UB_21      -0.1295383000
_diffrn_orient_matrix_UB_22      -0.0240032000
_diffrn_orient_matrix_UB_23      -0.0533313000
_diffrn_orient_matrix_UB_31      0.0372416000
_diffrn_orient_matrix_UB_32      -0.1650581000
_diffrn_orient_matrix_UB_33      -0.0008985000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2016
_reflns_number_total             2760
_reflns_odcompleteness_completeness 99.63
_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 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.302
_refine_diff_density_min         -0.241
_refine_diff_density_rms         0.059
_refine_ls_extinction_coef       0.0030(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         2760
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0746
_refine_ls_R_factor_gt           0.0567
_refine_ls_restrained_S_all      1.016
_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)+(0.0961P)²+0.0735P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1488
_refine_ls_wR_factor_ref         0.1723
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C18(H18)
2.b Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C10(H10), C11(H11), C12(H12), C13(H13),
 C17(H17)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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 0.7156(3) 0.8514(3) 0.59474(10) 0.0935(7) Uani 1 1 d . . . . .
F2 F 0.6015(2) 1.0563(3) 0.59207(11) 0.0990(8) Uani 1 1 d . . . . .
F3 F 0.8211(2) 1.0350(3) 0.64121(12) 0.0997(8) Uani 1 1 d . . . . .
F4 F 0.1805(2) 1.3116(2) 0.53321(9) 0.0810(6) Uani 1 1 d . . . . .
F5 F 0.4183(2) 1.34585(19) 0.56894(9) 0.0760(6) Uani 1 1 d . . . . .
O1 O 0.6724(3) 0.9700(2) 0.74845(11) 0.0716(6) Uani 1 1 d . . . . .
N1 N 0.4655(2) 0.8675(2) 0.69381(10) 0.0472(5) Uani 1 1 d . . . . .
C1 C 0.1616(3) 0.9152(3) 0.56325(12) 0.0480(6) Uani 1 1 d . . . . .
H1 H 0.0832 0.9817 0.5517 0.058 Uiso 1 1 calc R . . . .
C2 C 0.1815(3) 0.7893(3) 0.52544(12) 0.0537(6) Uani 1 1 d . . . . .
H2 H 0.1168 0.7721 0.4885 0.064 Uiso 1 1 calc R . . . .
C3 C 0.2962(3) 0.6900(3) 0.54230(13) 0.0573(7) Uani 1 1 d . . . . .
H3 H 0.3092 0.6061 0.5166 0.069 Uiso 1 1 calc R . . . .
C4 C 0.3926(3) 0.7140(3) 0.59734(14) 0.0554(7) Uani 1 1 d . . . . .
H4 H 0.4688 0.6458 0.6094 0.067 Uiso 1 1 calc R . . . .
C5 C 0.3740(3) 0.8409(3) 0.63418(11) 0.0435(6) Uani 1 1 d . . . . .
C6 C 0.2585(3) 0.9428(2) 0.61847(11) 0.0400(5) Uani 1 1 d . . . . .
C7 C 0.2382(3) 1.0750(3) 0.66132(11) 0.0416(5) Uani 1 1 d . . . . .
C8 C 0.1929(3) 1.0536(3) 0.73267(11) 0.0447(6) Uani 1 1 d . . . . .
C9 C 0.2597(3) 0.9483(3) 0.77526(12) 0.0480(6) Uani 1 1 d . . . . .
C10 C 0.2080(4) 0.9399(4) 0.84112(14) 0.0640(8) Uani 1 1 d . . . . .
H10 H 0.2532 0.8713 0.8698 0.077 Uiso 1 1 calc R . . . .
C11 C 0.0921(4) 1.0301(4) 0.86474(14) 0.0734(9) Uani 1 1 d . . . . .
H11 H 0.0591 1.0220 0.9087 0.088 Uiso 1 1 calc R . . . .
C12 C 0.0254(4) 1.1324(4) 0.82275(15) 0.0718(9) Uani 1 1 d . . . . .
H12 H -0.0536 1.1933 0.8383 0.086 Uiso 1 1 calc R . . . .
C13 C 0.0751(3) 1.1451(3) 0.75779(14) 0.0586(7) Uani 1 1 d . . . . .
H13 H 0.0298 1.2155 0.7300 0.070 Uiso 1 1 calc R . . . .
C14 C 0.3822(3) 0.8373(3) 0.75617(13) 0.0558(7) Uani 1 1 d . . . . .
H14A H 0.4589 0.8309 0.7923 0.067 Uiso 1 1 calc R . . . .
H14B H 0.3321 0.7423 0.7522 0.067 Uiso 1 1 calc R . . . .
C15 C 0.6060(3) 0.9348(3) 0.69708(13) 0.0502(6) Uani 1 1 d . . . . .
C16 C 0.6864(3) 0.9689(3) 0.63044(15) 0.0599(7) Uani 1 1 d . . . . .
C17 C 0.2536(3) 1.2097(3) 0.63656(12) 0.0462(6) Uani 1 1 d . . . . .
H17 H 0.2335 1.2879 0.6650 0.055 Uiso 1 1 calc R . . . .
C18 C 0.3003(3) 1.2447(3) 0.56718(12) 0.0516(6) Uani 1 1 d . . . . .
H18 H 0.3337 1.1560 0.5437 0.062 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 C16 1.314(4) . ?
F2 C16 1.317(3) . ?
F3 C16 1.314(3) . ?
F4 C18 1.364(3) . ?
F5 C18 1.366(3) . ?
O1 C15 1.210(3) . ?
N1 C5 1.438(3) . ?
N1 C14 1.468(3) . ?
N1 C15 1.348(3) . ?
C1 H1 0.9300 . ?
C1 C2 1.387(4) . ?
C1 C6 1.394(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.373(4) . ?
C3 H3 0.9300 . ?
C3 C4 1.383(4) . ?
C4 H4 0.9300 . ?
C4 C5 1.383(4) . ?
C5 C6 1.388(3) . ?
C6 C7 1.491(3) . ?
C7 C8 1.495(3) . ?
C7 C17 1.332(3) . ?
C8 C9 1.400(4) . ?
C8 C13 1.404(4) . ?
C9 C10 1.396(3) . ?
C9 C14 1.508(4) . ?
C10 H10 0.9300 . ?
C10 C11 1.374(4) . ?
C11 H11 0.9300 . ?
C11 C12 1.374(5) . ?
C12 H12 0.9300 . ?
C12 C13 1.376(4) . ?
C13 H13 0.9300 . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 C16 1.538(4) . ?
C17 H17 0.9300 . ?
C17 C18 1.483(3) . ?
C18 H18 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C5 N1 C14 114.2(2) . . ?
C15 N1 C5 126.2(2) . . ?
C15 N1 C14 118.9(2) . . ?
C2 C1 H1 119.8 . . ?
C2 C1 C6 120.4(2) . . ?
C6 C1 H1 119.8 . . ?
C1 C2 H2 119.8 . . ?
C3 C2 C1 120.3(2) . . ?
C3 C2 H2 119.8 . . ?
C2 C3 H3 119.8 . . ?
C2 C3 C4 120.4(2) . . ?
C4 C3 H3 119.8 . . ?
C3 C4 H4 120.5 . . ?
C5 C4 C3 119.1(2) . . ?
C5 C4 H4 120.5 . . ?
C4 C5 N1 121.3(2) . . ?
C4 C5 C6 121.8(2) . . ?
C6 C5 N1 116.8(2) . . ?
C1 C6 C7 122.0(2) . . ?
C5 C6 C1 118.1(2) . . ?
C5 C6 C7 119.9(2) . . ?
C6 C7 C8 118.4(2) . . ?
C17 C7 C6 121.4(2) . . ?
C17 C7 C8 120.2(2) . . ?
C9 C8 C7 124.2(2) . . ?
C9 C8 C13 118.6(2) . . ?
C13 C8 C7 117.2(2) . . ?
C8 C9 C14 125.8(2) . . ?
C10 C9 C8 118.8(2) . . ?
C10 C9 C14 115.4(2) . . ?
C9 C10 H10 119.1 . . ?
C11 C10 C9 121.8(3) . . ?
C11 C10 H10 119.1 . . ?
C10 C11 H11 120.3 . . ?
C10 C11 C12 119.4(3) . . ?
C12 C11 H11 120.3 . . ?
C11 C12 H12 119.9 . . ?
C11 C12 C13 120.3(3) . . ?
C13 C12 H12 119.9 . . ?
C8 C13 H13 119.4 . . ?
C12 C13 C8 121.2(3) . . ?
C12 C13 H13 119.4 . . ?
N1 C14 C9 115.6(2) . . ?
N1 C14 H14A 108.4 . . ?
N1 C14 H14B 108.4 . . ?
C9 C14 H14A 108.4 . . ?
C9 C14 H14B 108.4 . . ?
H14A C14 H14B 107.4 . . ?
O1 C15 N1 124.6(3) . . ?
O1 C15 C16 118.2(3) . . ?
N1 C15 C16 117.1(2) . . ?
F1 C16 F2 106.5(3) . . ?
F1 C16 C15 113.3(3) . . ?
F2 C16 C15 112.3(2) . . ?
F3 C16 F1 107.0(2) . . ?
F3 C16 F2 106.9(3) . . ?
F3 C16 C15 110.4(2) . . ?
C7 C17 H17 117.4 . . ?
C7 C17 C18 125.1(2) . . ?
C18 C17 H17 117.4 . . ?
F4 C18 F5 104.9(2) . . ?
F4 C18 C17 110.8(2) . . ?
F4 C18 H18 110.6 . . ?
F5 C18 C17 109.1(2) . . ?
F5 C18 H18 110.6 . . ?
C17 C18 H18 110.6 . . ?

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 C15 C16 F1 119.7(3) . . . . ?
O1 C15 C16 F2 -119.6(3) . . . . ?
O1 C15 C16 F3 -0.3(4) . . . . ?
N1 C5 C6 C1 -176.1(2) . . . . ?
N1 C5 C6 C7 2.2(3) . . . . ?
N1 C15 C16 F1 -60.4(3) . . . . ?
N1 C15 C16 F2 60.3(3) . . . . ?
N1 C15 C16 F3 179.5(2) . . . . ?
C1 C2 C3 C4 0.4(4) . . . . ?
C1 C6 C7 C8 115.6(2) . . . . ?
C1 C6 C7 C17 -61.7(3) . . . . ?
C2 C1 C6 C5 -0.1(3) . . . . ?
C2 C1 C6 C7 -178.5(2) . . . . ?
C2 C3 C4 C5 -1.4(4) . . . . ?
C3 C4 C5 N1 176.7(2) . . . . ?
C3 C4 C5 C6 1.8(4) . . . . ?
C4 C5 C6 C1 -1.0(3) . . . . ?
C4 C5 C6 C7 177.4(2) . . . . ?
C5 N1 C14 C9 -74.2(3) . . . . ?
C5 N1 C15 O1 171.5(2) . . . . ?
C5 N1 C15 C16 -8.3(4) . . . . ?
C5 C6 C7 C8 -62.7(3) . . . . ?
C5 C6 C7 C17 120.0(3) . . . . ?
C6 C1 C2 C3 0.4(4) . . . . ?
C6 C7 C8 C9 44.1(3) . . . . ?
C6 C7 C8 C13 -135.5(2) . . . . ?
C6 C7 C17 C18 -3.7(4) . . . . ?
C7 C8 C9 C10 179.5(2) . . . . ?
C7 C8 C9 C14 -2.2(4) . . . . ?
C7 C8 C13 C12 179.6(3) . . . . ?
C7 C17 C18 F4 114.5(3) . . . . ?
C7 C17 C18 F5 -130.5(3) . . . . ?
C8 C7 C17 C18 179.0(2) . . . . ?
C8 C9 C10 C11 1.1(4) . . . . ?
C8 C9 C14 N1 16.5(4) . . . . ?
C9 C8 C13 C12 0.0(4) . . . . ?
C9 C10 C11 C12 -0.4(5) . . . . ?
C10 C9 C14 N1 -165.2(2) . . . . ?
C10 C11 C12 C13 -0.5(5) . . . . ?
C11 C12 C13 C8 0.7(5) . . . . ?
C13 C8 C9 C10 -0.9(4) . . . . ?
C13 C8 C9 C14 177.4(2) . . . . ?
C14 N1 C5 C4 -100.5(3) . . . . ?
C14 N1 C5 C6 74.7(3) . . . . ?
C14 N1 C15 O1 1.8(4) . . . . ?
C14 N1 C15 C16 -178.0(2) . . . . ?
C14 C9 C10 C11 -177.3(3) . . . . ?
C15 N1 C5 C4 89.4(3) . . . . ?
C15 N1 C5 C6 -95.4(3) . . . . ?
C15 N1 C14 C9 96.7(3) . . . . ?
C17 C7 C8 C9 -138.5(3) . . . . ?
C17 C7 C8 C13 41.9(3) . . . . ?

_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 3.307
_oxdiff_exptl_absorpt_empirical_full_min 0.644
