# Supplementary Information (SI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2025

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_exp_1277
_audit_block_doi                 10.5517/ccdc.csd.cc2jjm3t
_database_code_depnum_ccdc_archive 'CCDC 2339666'
loop_
_audit_author_name
_audit_author_address
'Yaohui Liu'
;Shandong Normal University
China
;
_audit_update_record             
;
2024-03-12 deposited with the CCDC.	2024-12-12 downloaded from the CCDC.
;
_audit_creation_date             2023-03-06
_audit_creation_method           
;
  Olex2 1.2
  (compiled Apr 23 2013 17:54:37, GUI svn.r4466)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C17 H14 F3 N O'
_chemical_formula_sum            'C17 H14 F3 N O'
_chemical_formula_weight         305.29
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C1 H1 O1 N1 F1'
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'
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'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x+1/2, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   14.6371(4)
_cell_length_b                   12.8598(5)
_cell_length_c                   16.1477(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 94.065(3)
_cell_angle_gamma                90.00
_cell_volume                     3031.84(17)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    4044
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.1100
_cell_measurement_theta_min      3.9130
_exptl_absorpt_coefficient_mu    0.926
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.42444
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.338
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1264
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0500
_diffrn_reflns_av_unetI/netI     0.0556
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            13414
_diffrn_reflns_theta_full        67.06
_diffrn_reflns_theta_max         67.07
_diffrn_reflns_theta_min         3.94
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0793
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.9963
_diffrn_measured_fraction_theta_max 0.9764
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -70.00 -38.00   1.00    1.00    --    0.00 -53.00 -27.00   32
  2  ω    -24.00   7.00   1.00    1.00    --    0.00 -53.00 -27.00   31
  3  ω     -9.00  75.00   1.00    1.51    --   54.00 -53.00 -27.00   84
  4  ω     39.00 121.00   1.00    1.51    --   54.00  53.00 117.00   82
  5  ω     92.00 177.00   1.00    1.51    --  108.00  53.00 117.00   85
  6  ω     49.00 129.00   1.00    1.51    --  108.00 -53.00 -27.00   80
  7  ω    -12.00  14.00   1.00    1.00    --    0.00 -77.00-180.00   26
  8  ω    -18.00  12.00   1.00    1.00    --    0.00  53.00 117.00   30
  9  ω     22.00  67.00   1.00    1.00    --    0.00  53.00 117.00   45
 10  ω     26.00  52.00   1.00    1.51    --   54.00 -99.00-180.00   26
 11  ω     84.00 110.00   1.00    1.51    --   54.00  57.00 -60.00   26
 12  ω     25.00  96.00   1.00    1.51    --   54.00 -99.00 150.00   71
 13  ω      7.00  96.00   1.00    1.51    --   54.00 -99.00 -30.00   89
 14  ω     34.00  59.00   1.00    1.51    --   54.00  57.00 -60.00   25
 15  ω     69.00  95.00   1.00    1.51    --  108.00 -91.00-120.00   26
 16  ω     71.00 128.00   1.00    1.51    --  108.00 -63.00  60.00   57
 17  ω     88.00 178.00   1.00    1.51    --  108.00  50.00  60.00   90
 18  ω     50.00  99.00   1.00    1.51    --  108.00-111.00-180.00   49
 19  ω    105.00 169.00   1.00    1.51    --  108.00 111.00   0.00   64
 20  ω     38.00  63.00   1.00    1.51    --  108.00 -91.00   0.00   25
 21  ω     96.00 136.00   1.00    1.51    --  108.00  63.00 150.00   40
 22  ω     53.00 107.00   1.00    1.51    --  108.00 -91.00 -60.00   54
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0876136000
_diffrn_orient_matrix_UB_12      0.0540002000
_diffrn_orient_matrix_UB_13      -0.0256868000
_diffrn_orient_matrix_UB_21      0.0110896000
_diffrn_orient_matrix_UB_22      0.0542240000
_diffrn_orient_matrix_UB_23      0.0852076000
_diffrn_orient_matrix_UB_31      0.0578138000
_diffrn_orient_matrix_UB_32      -0.0921134000
_diffrn_orient_matrix_UB_33      0.0350493000
_diffrn_oxdiff_digest_frames     
;
01bbe8db051ecb97b30ccd4ac37a07fe3e0002858d4
;
_diffrn_oxdiff_digest_hkl        
;
012266f796286f3d76bc87a435a131df3d8853
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                3718
_reflns_number_total             5326
_reflns_odcompleteness_completeness 99.63
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
XL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    
;
XS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_refine_diff_density_max         0.441
_refine_diff_density_min         -0.414
_refine_diff_density_rms         0.053
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     427
_refine_ls_number_reflns         5326
_refine_ls_number_restraints     36
_refine_ls_R_factor_all          0.1056
_refine_ls_R_factor_gt           0.0735
_refine_ls_restrained_S_all      1.089
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0958P)²+2.4763P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1975
_refine_ls_wR_factor_ref         0.2268
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 F4'-C34 \\sim F5'-C34 \\sim F6'-C34
 with sigma of 0.01
 F4-C34 \\sim F5-C34 \\sim F6-C34
 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
F4 \\sim F5 \\sim F6 \\sim F4' \\sim F5' \\sim F6': within 1.7A with sigma of 0.005 and sigma for terminal atoms of 0.005
4. Others
 Sof(F4')=Sof(F5')=Sof(F6')=1-FVAR(1)
 Sof(F4)=Sof(F5)=Sof(F6)=FVAR(1)
5.a Ternary CH refined with riding coordinates:
 C8(H8), C25(H25)
5.b Aromatic/amide H refined with riding coordinates:
 C2(H2A), C3(H3), C4(H4), C5(H5), C10(H10), C11(H11), C12(H12), C13(H13),
 C14(H14), C19(H19), C20(H20), C21(H21), C22(H22), C27(H27), C28(H28), C29(H29),
  C30(H30), C31(H31), N1(H1), N2(H2)
5.c Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C32(H32A,H32B,H32C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.5700(2) 0.6766(3) 0.1810(2) 0.0497(8) Uani 1 1 d . . .
C2 C 0.5344(3) 0.7043(3) 0.1023(2) 0.0654(11) Uani 1 1 d . . .
H2A H 0.4745 0.6881 0.0837 0.078 Uiso 1 1 calc R . .
C3 C 0.5916(3) 0.7568(4) 0.0530(3) 0.0726(12) Uani 1 1 d . . .
H3 H 0.5697 0.7768 -0.0001 0.087 Uiso 1 1 calc R . .
C4 C 0.6819(3) 0.7809(3) 0.0806(3) 0.0696(11) Uani 1 1 d . . .
H4 H 0.7185 0.8170 0.0455 0.084 Uiso 1 1 calc R . .
C5 C 0.7176(2) 0.7526(3) 0.1580(2) 0.0555(9) Uani 1 1 d . . .
H5 H 0.7779 0.7683 0.1756 0.067 Uiso 1 1 calc R . .
C6 C 0.6607(2) 0.6991(3) 0.2101(2) 0.0452(7) Uani 1 1 d . . .
C7 C 0.67382(19) 0.6580(3) 0.29200(19) 0.0436(7) Uani 1 1 d . . .
C8 C 0.76037(19) 0.6643(3) 0.3486(2) 0.0462(8) Uani 1 1 d . . .
H8 H 0.7519 0.6217 0.3978 0.055 Uiso 1 1 calc R . .
C9 C 0.7808(2) 0.7741(3) 0.3772(2) 0.0479(8) Uani 1 1 d . . .
C10 C 0.7118(3) 0.8341(4) 0.4065(3) 0.0754(12) Uani 1 1 d . . .
H10 H 0.6533 0.8061 0.4073 0.091 Uiso 1 1 calc R . .
C11 C 0.7270(4) 0.9334(4) 0.4346(3) 0.0878(14) Uani 1 1 d . . .
H11 H 0.6792 0.9716 0.4543 0.105 Uiso 1 1 calc R . .
C12 C 0.8121(4) 0.9766(4) 0.4338(3) 0.0795(13) Uani 1 1 d . . .
H12 H 0.8225 1.0447 0.4515 0.095 Uiso 1 1 calc R . .
C13 C 0.8807(4) 0.9191(4) 0.4069(3) 0.0933(15) Uani 1 1 d . . .
H13 H 0.9392 0.9474 0.4071 0.112 Uiso 1 1 calc R . .
C14 C 0.8658(3) 0.8178(3) 0.3789(3) 0.0795(13) Uani 1 1 d . . .
H14 H 0.9145 0.7793 0.3611 0.095 Uiso 1 1 calc R . .
C15 C 0.8257(3) 0.5167(3) 0.2889(4) 0.0845(15) Uani 1 1 d . . .
H15A H 0.8154 0.4784 0.3385 0.127 Uiso 1 1 calc R . .
H15B H 0.8799 0.4912 0.2657 0.127 Uiso 1 1 calc R . .
H15C H 0.7741 0.5081 0.2494 0.127 Uiso 1 1 calc R . .
C16 C 0.59232(19) 0.6136(3) 0.3090(2) 0.0473(8) Uani 1 1 d . . .
C17 C 0.5672(2) 0.5591(3) 0.3843(3) 0.0630(10) Uani 1 1 d . . .
C18 C 0.0867(2) 0.5557(3) 0.3529(2) 0.0476(8) Uani 1 1 d . A .
C19 C 0.0567(2) 0.4804(3) 0.4065(2) 0.0550(9) Uani 1 1 d . . .
H19 H -0.0049 0.4739 0.4161 0.066 Uiso 1 1 calc R . .
C20 C 0.1212(2) 0.4164(3) 0.4445(2) 0.0604(9) Uani 1 1 d . . .
H20 H 0.1035 0.3661 0.4815 0.072 Uiso 1 1 calc R . .
C21 C 0.2136(2) 0.4253(3) 0.4288(2) 0.0600(10) Uani 1 1 d . . .
H21 H 0.2557 0.3793 0.4543 0.072 Uiso 1 1 calc R . .
C22 C 0.2436(2) 0.4995(3) 0.3771(2) 0.0564(9) Uani 1 1 d . . .
H22 H 0.3054 0.5046 0.3680 0.068 Uiso 1 1 calc R . .
C23 C 0.1800(2) 0.5682(3) 0.3378(2) 0.0482(8) Uani 1 1 d . . .
C24 C 0.1856(2) 0.6521(3) 0.2809(2) 0.0517(8) Uani 1 1 d . . .
C25 C 0.2727(2) 0.6963(3) 0.2491(2) 0.0596(10) Uani 1 1 d . . .
H25 H 0.2560 0.7389 0.2000 0.072 Uiso 1 1 calc R . .
C26 C 0.3292(2) 0.7622(3) 0.3112(2) 0.0557(9) Uani 1 1 d . . .
C27 C 0.3218(4) 0.7591(5) 0.3952(3) 0.110(2) Uani 1 1 d . . .
H27 H 0.2774 0.7169 0.4162 0.133 Uiso 1 1 calc R . .
C28 C 0.3780(5) 0.8163(5) 0.4493(4) 0.126(2) Uani 1 1 d . . .
H28 H 0.3721 0.8115 0.5061 0.152 Uiso 1 1 calc R . .
C29 C 0.4422(3) 0.8800(4) 0.4199(4) 0.0909(15) Uani 1 1 d . . .
H29 H 0.4820 0.9173 0.4562 0.109 Uiso 1 1 calc R . .
C30 C 0.4472(3) 0.8880(4) 0.3377(4) 0.0911(15) Uani 1 1 d . . .
H30 H 0.4892 0.9339 0.3171 0.109 Uiso 1 1 calc R . .
C31 C 0.3918(3) 0.8301(3) 0.2828(3) 0.0711(11) Uani 1 1 d . . .
H31 H 0.3970 0.8372 0.2260 0.085 Uiso 1 1 calc R . .
C32 C 0.2953(3) 0.5569(5) 0.1548(3) 0.113(2) Uani 1 1 d . . .
H32A H 0.2389 0.5244 0.1674 0.170 Uiso 1 1 calc R . .
H32B H 0.3383 0.5046 0.1408 0.170 Uiso 1 1 calc R . .
H32C H 0.2841 0.6035 0.1087 0.170 Uiso 1 1 calc R . .
C33 C 0.0980(2) 0.6851(3) 0.2623(2) 0.0590(9) Uani 1 1 d . A .
C34 C 0.0626(3) 0.7670(4) 0.2065(3) 0.0913(16) Uani 1 1 d D . .
F1 F 0.6170(2) 0.4746(3) 0.4004(2) 0.1149(11) Uani 1 1 d . . .
F2 F 0.48139(15) 0.5288(3) 0.38015(17) 0.1059(11) Uani 1 1 d . . .
F3 F 0.5819(2) 0.6150(3) 0.45277(15) 0.1026(10) Uani 1 1 d . . .
N1 N 0.52976(16) 0.6233(2) 0.24219(17) 0.0521(7) Uani 1 1 d . . .
H1 H 0.4746 0.5999 0.2392 0.063 Uiso 1 1 calc R . .
N2 N 0.03801(17) 0.6282(2) 0.30554(19) 0.0573(8) Uani 1 1 d . . .
H2 H -0.0204 0.6365 0.3033 0.069 Uiso 1 1 calc R A .
O1 O 0.83682(14) 0.62389(19) 0.30862(16) 0.0564(6) Uani 1 1 d . . .
O2 O 0.33182(14) 0.6138(2) 0.22531(15) 0.0682(8) Uani 1 1 d . . .
F4 F 0.0558(7) 0.8590(6) 0.2494(6) 0.136(2) Uani 0.560(8) 1 d PDU A 1
F5 F -0.0240(5) 0.7473(8) 0.1784(7) 0.109(3) Uani 0.560(8) 1 d PDU A 1
F6 F 0.1074(5) 0.7957(8) 0.1425(6) 0.124(2) Uani 0.560(8) 1 d PDU A 1
F4' F 0.0849(8) 0.7402(10) 0.1307(6) 0.135(3) Uani 0.440(8) 1 d PDU A 2
F5' F 0.1056(7) 0.8571(7) 0.2163(8) 0.133(2) Uani 0.440(8) 1 d PDU A 2
F6' F -0.0237(7) 0.7895(10) 0.2073(9) 0.115(3) Uani 0.440(8) 1 d PDU 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
C1 C2 1.386(5) . ?
C1 C6 1.406(4) . ?
C1 N1 1.369(4) . ?
C2 C3 1.372(6) . ?
C3 C4 1.400(6) . ?
C4 C5 1.370(5) . ?
C5 C6 1.406(5) . ?
C6 C7 1.424(4) . ?
C7 C8 1.511(4) . ?
C7 C16 1.368(4) . ?
C8 C9 1.508(5) . ?
C8 O1 1.429(4) . ?
C9 C10 1.380(5) . ?
C9 C14 1.364(5) . ?
C10 C11 1.368(6) . ?
C11 C12 1.365(7) . ?
C12 C13 1.343(7) . ?
C13 C14 1.391(6) . ?
C15 O1 1.421(5) . ?
C16 C17 1.472(5) . ?
C16 N1 1.371(4) . ?
C17 F1 1.324(5) . ?
C17 F2 1.312(4) . ?
C17 F3 1.324(5) . ?
C18 C19 1.390(5) . ?
C18 C23 1.413(4) . ?
C18 N2 1.373(4) . ?
C19 C20 1.366(5) . ?
C20 C21 1.397(5) . ?
C21 C22 1.360(5) . ?
C22 C23 1.402(5) . ?
C23 C24 1.424(5) . ?
C24 C25 1.517(4) . ?
C24 C33 1.364(4) . ?
C25 C26 1.514(5) . ?
C25 O2 1.439(5) . ?
C26 C27 1.369(6) . ?
C26 C31 1.368(5) . ?
C27 C28 1.370(7) . ?
C28 C29 1.358(7) . ?
C29 C30 1.339(7) . ?
C30 C31 1.377(6) . ?
C32 O2 1.425(5) . ?
C33 C34 1.457(6) . ?
C33 N2 1.372(4) . ?
C34 F4 1.379(7) . ?
C34 F5 1.340(7) . ?
C34 F6 1.315(8) . ?
C34 F4' 1.334(9) . ?
C34 F5' 1.323(9) . ?
C34 F6' 1.298(9) . ?

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 C1 C6 122.5(3) . . ?
N1 C1 C2 129.6(3) . . ?
N1 C1 C6 107.8(3) . . ?
C3 C2 C1 117.0(4) . . ?
C2 C3 C4 121.7(4) . . ?
C5 C4 C3 121.5(4) . . ?
C4 C5 C6 118.2(3) . . ?
C1 C6 C7 107.2(3) . . ?
C5 C6 C1 119.1(3) . . ?
C5 C6 C7 133.7(3) . . ?
C6 C7 C8 126.4(3) . . ?
C16 C7 C6 106.2(3) . . ?
C16 C7 C8 127.3(3) . . ?
C9 C8 C7 112.0(3) . . ?
O1 C8 C7 110.9(3) . . ?
O1 C8 C9 109.5(2) . . ?
C10 C9 C8 119.6(3) . . ?
C14 C9 C8 123.5(3) . . ?
C14 C9 C10 116.8(4) . . ?
C11 C10 C9 122.0(4) . . ?
C12 C11 C10 120.2(5) . . ?
C13 C12 C11 118.8(4) . . ?
C12 C13 C14 121.2(4) . . ?
C9 C14 C13 120.9(4) . . ?
C7 C16 C17 129.6(3) . . ?
C7 C16 N1 110.3(3) . . ?
N1 C16 C17 120.1(3) . . ?
F1 C17 C16 112.7(3) . . ?
F1 C17 F3 103.1(3) . . ?
F2 C17 C16 113.2(3) . . ?
F2 C17 F1 106.2(4) . . ?
F2 C17 F3 107.6(3) . . ?
F3 C17 C16 113.3(3) . . ?
C19 C18 C23 122.6(3) . . ?
N2 C18 C19 130.2(3) . . ?
N2 C18 C23 107.2(3) . . ?
C20 C19 C18 117.4(3) . . ?
C19 C20 C21 121.0(4) . . ?
C22 C21 C20 121.8(3) . . ?
C21 C22 C23 119.1(3) . . ?
C18 C23 C24 107.4(3) . . ?
C22 C23 C18 118.0(3) . . ?
C22 C23 C24 134.6(3) . . ?
C23 C24 C25 126.2(3) . . ?
C33 C24 C23 106.3(3) . . ?
C33 C24 C25 127.4(3) . . ?
C26 C25 C24 114.7(3) . . ?
O2 C25 C24 110.5(3) . . ?
O2 C25 C26 106.2(3) . . ?
C27 C26 C25 124.2(3) . . ?
C31 C26 C25 118.9(3) . . ?
C31 C26 C27 116.9(4) . . ?
C26 C27 C28 122.0(4) . . ?
C29 C28 C27 120.0(5) . . ?
C30 C29 C28 118.7(5) . . ?
C29 C30 C31 121.7(4) . . ?
C26 C31 C30 120.5(4) . . ?
C24 C33 C34 130.4(3) . . ?
C24 C33 N2 110.3(3) . . ?
N2 C33 C34 119.2(3) . . ?
F4 C34 C33 110.2(5) . . ?
F5 C34 C33 111.1(5) . . ?
F5 C34 F4 103.4(6) . . ?
F6 C34 C33 120.9(5) . . ?
F6 C34 F4 102.2(6) . . ?
F6 C34 F5 107.4(7) . . ?
F6 C34 F4' 35.3(6) . . ?
F6 C34 F5' 65.7(6) . . ?
F4' C34 C33 106.4(6) . . ?
F4' C34 F4 135.5(7) . . ?
F4' C34 F5 85.8(7) . . ?
F5' C34 C33 114.5(5) . . ?
F5' C34 F4 40.4(5) . . ?
F5' C34 F5 129.5(7) . . ?
F5' C34 F4' 101.0(7) . . ?
F6' C34 C33 117.3(7) . . ?
F6' C34 F4 72.4(7) . . ?
F6' C34 F5 31.4(7) . . ?
F6' C34 F6 119.0(8) . . ?
F6' C34 F4' 111.6(9) . . ?
F6' C34 F5' 104.9(8) . . ?
C1 N1 C16 108.4(2) . . ?
C33 N2 C18 108.7(3) . . ?
C15 O1 C8 111.9(3) . . ?
C32 O2 C25 113.2(3) . . ?

_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.010
_oxdiff_exptl_absorpt_empirical_full_min 0.446

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_exp_1457
_audit_block_doi                 10.5517/ccdc.csd.cc2jjm8z
_database_code_depnum_ccdc_archive 'CCDC 2339671'
loop_
_audit_author_name
_audit_author_address
'Yaohui Liu'
;Shandong Normal University
China
;
_audit_update_record             
;
2024-03-12 deposited with the CCDC.	2024-12-12 downloaded from the CCDC.
;
_audit_creation_date             2023-05-11
_audit_creation_method           
;
  Olex2 1.2
  (compiled Apr 23 2013 17:54:37, GUI svn.r4466)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C17 H12 F3 N O'
_chemical_formula_sum            'C17 H12 F3 N O'
_chemical_formula_weight         303.28
_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'
N N 0.0311 0.0180 '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'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x+1/2, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   10.6930(7)
_cell_length_b                   7.2066(4)
_cell_length_c                   19.6695(11)
_cell_angle_alpha                90.00
_cell_angle_beta                 104.091(7)
_cell_angle_gamma                90.00
_cell_volume                     1470.13(15)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1226
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      66.5040
_cell_measurement_theta_min      4.6120
_exptl_absorpt_coefficient_mu    0.954
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.78134
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.370
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.15
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0320
_diffrn_reflns_av_unetI/netI     0.0414
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            5973
_diffrn_reflns_theta_full        67.04
_diffrn_reflns_theta_max         67.05
_diffrn_reflns_theta_min         4.33
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0793
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.9909
_diffrn_measured_fraction_theta_max 0.9734
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω      1.00  69.00   1.00    1.00    --    0.00  12.00-124.00   68
  2  ω    -50.00   4.00   1.00    1.00    --    0.00 -12.00  62.00   54
  3  ω     30.00  55.00   1.00    2.50    --   54.00  12.00-124.00   25
  4  ω    -18.00  97.00   1.00    2.50    --   54.00 -12.00  62.00  115
  5  ω     39.00 122.00   1.00    2.50    --  108.00  12.00-124.00   83
  6  ω     82.00 107.00   1.00    2.50    --  108.00 -12.00  62.00   25
  7  ω    -17.00  30.00   1.00    1.00    --    0.00 -77.00-150.00   47
  8  ω    -15.00  15.00   1.00    2.50    --   54.00 -57.00  60.00   30
  9  ω     31.00  92.00   1.00    2.50    --   54.00 -99.00  60.00   61
 10  ω     34.00 119.00   1.00    2.50    --   54.00  57.00  30.00   85
 11  ω     21.00  75.00   1.00    2.50    --   54.00 -57.00  60.00   54
 12  ω     58.00 129.00   1.00    2.50    --  108.00 -63.00  90.00   71
 13  ω     55.00 129.00   1.00    2.50    --  108.00 -50.00   0.00   74
 14  ω     62.00  87.00   1.00    2.50    --  108.00 178.00  60.00   25
 15  ω     80.00 109.00   1.00    2.50    --  108.00-111.00-150.00   29
 16  ω    118.00 145.00   1.00    2.50    --  108.00 178.00  60.00   27
 17  ω     44.00  76.00   1.00    2.50    --  108.00-111.00-150.00   32
 18  ω     75.00 178.00   1.00    2.50    --  108.00  25.00 -90.00  103
 19  ω     46.00 127.00   1.00    2.50    --  108.00 -77.00-150.00   81
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1219544000
_diffrn_orient_matrix_UB_12      0.0292135000
_diffrn_orient_matrix_UB_13      0.0596251000
_diffrn_orient_matrix_UB_21      0.0842942000
_diffrn_orient_matrix_UB_22      -0.0163731000
_diffrn_orient_matrix_UB_23      -0.0530053000
_diffrn_orient_matrix_UB_31      -0.0100589000
_diffrn_orient_matrix_UB_32      0.2111474000
_diffrn_orient_matrix_UB_33      -0.0123672000
_diffrn_oxdiff_digest_frames     
;
0146ae4f691fc2afed42c885325214f98100028fd05
;
_diffrn_oxdiff_digest_hkl        
;
015be505a636392f1b9a717dd38ca4ffdcbff5
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                1411
_reflns_number_total             2606
_reflns_odcompleteness_completeness 99.09
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
XL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    
;
XS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_refine_diff_density_max         0.175
_refine_diff_density_min         -0.207
_refine_diff_density_rms         0.046
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.157
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         2606
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1176
_refine_ls_R_factor_gt           0.0702
_refine_ls_restrained_S_all      1.157
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0858P)²+0.3162P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1976
_refine_ls_wR_factor_ref         0.2266
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_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. Others
 Sof(F1')=Sof(F2')=Sof(F3')=1-FVAR(1)
 Sof(F1)=Sof(F2)=Sof(F3)=FVAR(1)
3.a Aromatic/amide H refined with riding coordinates:
 C8(H8), C5(H5), C3(H3), C2(H2), C16(H16), C12(H12), C14(H14), C15(H15),
 C13(H13)
3.b Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.7202(3) 0.2939(4) 0.91400(12) 0.0849(9) Uani 1 1 d . . .
N1 N 0.7996(3) 0.3166(4) 0.64828(14) 0.0641(8) Uani 1 1 d . . .
C6 C 0.6442(3) 0.3138(4) 0.72117(15) 0.0515(8) Uani 1 1 d . . .
C1 C 0.7713(3) 0.3196(5) 0.71231(16) 0.0558(8) Uani 1 1 d . . .
C7 C 0.5409(3) 0.3099(4) 0.65956(16) 0.0554(8) Uani 1 1 d . . .
C9 C 0.7012(3) 0.3067(5) 0.59325(16) 0.0608(9) Uani 1 1 d . A .
C4 C 0.7274(3) 0.3066(5) 0.84650(16) 0.0634(9) Uani 1 1 d . . .
C8 C 0.5723(3) 0.3047(5) 0.59592(16) 0.0607(9) Uani 1 1 d . . .
H8 H 0.5076 0.2999 0.5547 0.073 Uiso 1 1 calc R . .
C11 C 0.4031(3) 0.3076(5) 0.66177(15) 0.0610(9) Uani 1 1 d . . .
C5 C 0.6245(3) 0.3062(5) 0.78962(16) 0.0606(9) Uani 1 1 d . . .
H5 H 0.5411 0.3009 0.7959 0.073 Uiso 1 1 calc R . .
C3 C 0.8537(3) 0.3174(5) 0.83763(18) 0.0684(10) Uani 1 1 d . . .
H3 H 0.9231 0.3195 0.8768 0.082 Uiso 1 1 calc R . .
C2 C 0.8753(3) 0.3249(5) 0.77270(19) 0.0674(10) Uani 1 1 d . . .
H2 H 0.9594 0.3335 0.7677 0.081 Uiso 1 1 calc R . .
C17 C 0.7337(4) 0.3016(7) 0.5224(2) 0.0768(11) Uani 1 1 d . . .
C16 C 0.3238(4) 0.1686(6) 0.62757(19) 0.0826(12) Uani 1 1 d . . .
H16 H 0.3581 0.0739 0.6056 0.099 Uiso 1 1 calc R . .
C12 C 0.3498(3) 0.4450(7) 0.69484(19) 0.0814(12) Uani 1 1 d . . .
H12 H 0.4019 0.5393 0.7187 0.098 Uiso 1 1 calc R . .
C14 C 0.1424(4) 0.3058(9) 0.6577(2) 0.1041(18) Uani 1 1 d . . .
H14 H 0.0546 0.3057 0.6558 0.125 Uiso 1 1 calc R . .
C15 C 0.1945(4) 0.1684(8) 0.6256(2) 0.1049(17) Uani 1 1 d . . .
H15 H 0.1421 0.0739 0.6021 0.126 Uiso 1 1 calc R . .
C13 C 0.2198(4) 0.4438(8) 0.6929(2) 0.1016(16) Uani 1 1 d . . .
H13 H 0.1849 0.5367 0.7154 0.122 Uiso 1 1 calc R . .
C22 C 0.5954(4) 0.2784(8) 0.9266(2) 0.1080(17) Uani 1 1 d . . .
H22A H 0.5519 0.1729 0.9018 0.162 Uiso 1 1 calc R . .
H22B H 0.5469 0.3888 0.9107 0.162 Uiso 1 1 calc R . .
H22C H 0.6031 0.2628 0.9759 0.162 Uiso 1 1 calc R . .
F1 F 0.6781(15) 0.1557(13) 0.4885(6) 0.137(5) Uani 0.70(2) 1 d P A 1
F2 F 0.6876(13) 0.4391(17) 0.4854(4) 0.121(4) Uani 0.70(2) 1 d P A 1
F3 F 0.8543(9) 0.289(3) 0.5259(5) 0.140(6) Uani 0.70(2) 1 d P A 1
F1' F 0.784(6) 0.453(4) 0.5040(16) 0.170(17) Uani 0.30(2) 1 d P A 2
F2' F 0.820(3) 0.176(4) 0.5197(15) 0.128(10) Uani 0.30(2) 1 d P A 2
F3' F 0.6402(17) 0.254(7) 0.4691(9) 0.157(16) Uani 0.30(2) 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
O1 C4 1.352(4) . ?
O1 C22 1.420(5) . ?
N1 C1 1.365(4) . ?
N1 C9 1.315(4) . ?
C6 C1 1.412(4) . ?
C6 C7 1.428(4) . ?
C6 C5 1.414(4) . ?
C1 C2 1.417(4) . ?
C7 C8 1.374(4) . ?
C7 C11 1.484(4) . ?
C9 C8 1.391(4) . ?
C9 C17 1.517(5) . ?
C4 C5 1.365(4) . ?
C4 C3 1.405(5) . ?
C8 H8 0.9300 . ?
C11 C16 1.377(5) . ?
C11 C12 1.382(5) . ?
C5 H5 0.9300 . ?
C3 H3 0.9300 . ?
C3 C2 1.353(5) . ?
C2 H2 0.9300 . ?
C17 F1 1.308(10) . ?
C17 F2 1.257(8) . ?
C17 F3 1.277(9) . ?
C17 F1' 1.307(14) . ?
C17 F2' 1.30(2) . ?
C17 F3' 1.306(15) . ?
C16 H16 0.9300 . ?
C16 C15 1.373(6) . ?
C12 H12 0.9300 . ?
C12 C13 1.381(5) . ?
C14 H14 0.9300 . ?
C14 C15 1.365(7) . ?
C14 C13 1.368(7) . ?
C15 H15 0.9300 . ?
C13 H13 0.9300 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 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
C4 O1 C22 117.3(3) . . ?
C9 N1 C1 116.6(3) . . ?
C1 C6 C7 117.7(3) . . ?
C1 C6 C5 119.3(3) . . ?
C5 C6 C7 122.9(3) . . ?
N1 C1 C6 123.3(3) . . ?
N1 C1 C2 118.0(3) . . ?
C6 C1 C2 118.7(3) . . ?
C6 C7 C11 122.9(3) . . ?
C8 C7 C6 117.6(3) . . ?
C8 C7 C11 119.4(3) . . ?
N1 C9 C8 124.8(3) . . ?
N1 C9 C17 116.2(3) . . ?
C8 C9 C17 119.0(3) . . ?
O1 C4 C5 125.2(3) . . ?
O1 C4 C3 114.4(3) . . ?
C5 C4 C3 120.4(3) . . ?
C7 C8 C9 119.9(3) . . ?
C7 C8 H8 120.0 . . ?
C9 C8 H8 120.0 . . ?
C16 C11 C7 119.4(3) . . ?
C16 C11 C12 118.4(3) . . ?
C12 C11 C7 122.1(3) . . ?
C6 C5 H5 119.9 . . ?
C4 C5 C6 120.2(3) . . ?
C4 C5 H5 119.9 . . ?
C4 C3 H3 119.7 . . ?
C2 C3 C4 120.6(3) . . ?
C2 C3 H3 119.7 . . ?
C1 C2 H2 119.6 . . ?
C3 C2 C1 120.7(3) . . ?
C3 C2 H2 119.6 . . ?
F1 C17 C9 108.1(5) . . ?
F2 C17 C9 111.6(4) . . ?
F2 C17 F1 105.8(6) . . ?
F2 C17 F3 109.7(7) . . ?
F2 C17 F1' 46(2) . . ?
F2 C17 F2' 134.9(11) . . ?
F2 C17 F3' 68.0(18) . . ?
F3 C17 C9 114.0(5) . . ?
F3 C17 F1 107.3(8) . . ?
F3 C17 F1' 66.3(19) . . ?
F3 C17 F2' 40.3(11) . . ?
F3 C17 F3' 126.2(10) . . ?
F1' C17 C9 115.9(8) . . ?
F1' C17 F1 134.2(10) . . ?
F2' C17 C9 112.2(12) . . ?
F2' C17 F1 70.0(15) . . ?
F2' C17 F1' 103.2(15) . . ?
F2' C17 F3' 101.3(16) . . ?
F3' C17 C9 116.2(8) . . ?
F3' C17 F1 38.4(19) . . ?
F3' C17 F1' 106.4(14) . . ?
C11 C16 H16 119.6 . . ?
C15 C16 C11 120.7(4) . . ?
C15 C16 H16 119.6 . . ?
C11 C12 H12 119.7 . . ?
C13 C12 C11 120.6(4) . . ?
C13 C12 H12 119.7 . . ?
C15 C14 H14 120.1 . . ?
C15 C14 C13 119.8(4) . . ?
C13 C14 H14 120.1 . . ?
C16 C15 H15 119.7 . . ?
C14 C15 C16 120.5(4) . . ?
C14 C15 H15 119.7 . . ?
C12 C13 H13 120.0 . . ?
C14 C13 C12 120.0(5) . . ?
C14 C13 H13 120.0 . . ?
O1 C22 H22A 109.5 . . ?
O1 C22 H22B 109.5 . . ?
O1 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 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 C4 C5 C6 -177.8(3) . . . . ?
O1 C4 C3 C2 177.9(3) . . . . ?
N1 C1 C2 C3 -176.2(3) . . . . ?
N1 C9 C8 C7 -1.2(6) . . . . ?
N1 C9 C17 F1 125.8(8) . . . . ?
N1 C9 C17 F2 -118.2(9) . . . . ?
N1 C9 C17 F3 6.7(13) . . . . ?
N1 C9 C17 F1' -67(3) . . . . ?
N1 C9 C17 F2' 51(2) . . . . ?
N1 C9 C17 F3' 166(3) . . . . ?
C6 C1 C2 C3 2.5(5) . . . . ?
C6 C7 C8 C9 -1.1(5) . . . . ?
C6 C7 C11 C16 -125.0(4) . . . . ?
C6 C7 C11 C12 57.7(5) . . . . ?
C1 N1 C9 C8 2.0(5) . . . . ?
C1 N1 C9 C17 -179.4(3) . . . . ?
C1 C6 C7 C8 2.5(5) . . . . ?
C1 C6 C7 C11 -178.7(3) . . . . ?
C1 C6 C5 C4 0.8(5) . . . . ?
C7 C6 C1 N1 -1.8(5) . . . . ?
C7 C6 C1 C2 179.6(3) . . . . ?
C7 C6 C5 C4 178.7(3) . . . . ?
C7 C11 C16 C15 -176.5(4) . . . . ?
C7 C11 C12 C13 176.7(4) . . . . ?
C9 N1 C1 C6 -0.4(5) . . . . ?
C9 N1 C1 C2 178.2(3) . . . . ?
C4 C3 C2 C1 -0.8(6) . . . . ?
C8 C7 C11 C16 53.8(5) . . . . ?
C8 C7 C11 C12 -123.6(4) . . . . ?
C8 C9 C17 F1 -55.5(9) . . . . ?
C8 C9 C17 F2 60.5(10) . . . . ?
C8 C9 C17 F3 -174.7(11) . . . . ?
C8 C9 C17 F1' 111(3) . . . . ?
C8 C9 C17 F2' -131(2) . . . . ?
C8 C9 C17 F3' -15(3) . . . . ?
C11 C7 C8 C9 -179.9(3) . . . . ?
C11 C16 C15 C14 -0.3(7) . . . . ?
C11 C12 C13 C14 -0.2(7) . . . . ?
C5 C6 C1 N1 176.2(3) . . . . ?
C5 C6 C1 C2 -2.4(5) . . . . ?
C5 C6 C7 C8 -175.4(3) . . . . ?
C5 C6 C7 C11 3.3(5) . . . . ?
C5 C4 C3 C2 -1.0(6) . . . . ?
C3 C4 C5 C6 1.0(5) . . . . ?
C17 C9 C8 C7 -179.8(4) . . . . ?
C16 C11 C12 C13 -0.7(6) . . . . ?
C12 C11 C16 C15 1.0(6) . . . . ?
C15 C14 C13 C12 0.9(7) . . . . ?
C13 C14 C15 C16 -0.7(7) . . . . ?
C22 O1 C4 C5 0.2(6) . . . . ?
C22 O1 C4 C3 -178.6(4) . . . . ?

_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.193
_oxdiff_exptl_absorpt_empirical_full_min 0.772

