# Supplementary Information (SI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 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_975490
_database_code_depnum_ccdc_archive 'CCDC 2449181'
loop_
_audit_author_name
_audit_author_address
'shizhou Yang'
;Chongqing University of Technology 
China
;
_audit_update_record             
;
2025-05-07 deposited with the CCDC.	2026-02-26 downloaded from the CCDC.
;
_audit_creation_date             2025-04-15
_audit_creation_method           
;
Olex2 1.5-beta
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H17 F4 N'
_chemical_formula_sum            'C23 H17 F4 N'
_chemical_formula_weight         383.38
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C  H O N F'
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'

_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                   9.9386(5)
_cell_length_b                   11.3326(5)
_cell_length_c                   18.1315(9)
_cell_angle_alpha                74.496(4)
_cell_angle_beta                 87.854(4)
_cell_angle_gamma                65.355(4)
_cell_volume                     1782.20(16)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    15561
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      74.4530
_cell_measurement_theta_min      2.5300
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.952
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.76909
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.143a (Rigaku Oxford Diffraction, 2024)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.429
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             792
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0172
_diffrn_reflns_av_unetI/netI     0.0122
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.942
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            18902
_diffrn_reflns_point_group_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.942
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.568
_diffrn_reflns_theta_min         2.538
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.942
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     33.00 120.00   0.50    0.05    --   43.18  38.00-180.00  174
  2  ω    130.00 167.00   0.50    0.05    --  106.94  30.00 -30.00   74
  3  ω     94.00 120.00   0.50    0.05    --  106.94  30.00 -30.00   52
  4  ω     93.00 137.00   0.50    0.05    --  106.94  15.00-180.00   88
  5  ω     94.00 120.00   0.50    0.05    --  106.94  30.00  60.00   52
  6  ω    110.00 138.00   0.50    0.05    --  106.94  15.00  30.00   56
  7  ω    136.00 169.00   0.50    0.05    --  106.94  30.00  60.00   66
  8  ω     94.00 139.00   0.50    0.05    --  106.94  15.00 120.00   90
  9  ω     96.00 123.00   0.50    0.05    --  106.94  15.00 150.00   54
 10  ω     33.00  74.00   0.50    0.05    --  106.94 -77.00  30.00   82
 11  ω     37.00  64.00   0.50    0.05    --  106.94 -77.00 120.00   54
 12  ω    105.00 130.00   0.50    0.05    --  106.94 130.00 -97.00   50
 13  ω     52.00  77.00   0.50    0.05    --  106.94 -77.00-120.00   50
 14  ω     61.00  86.00   0.50    0.05    --   43.18-130.00-169.00   50
 15  ω     64.00  90.00   0.50    0.05    --  106.94-130.00-169.00   52
 16  ω     48.00  96.00   0.50    0.05    --  106.94-126.00-150.00   96
 17  ω     36.00  69.00   0.50    0.05    --  106.94-126.00-120.00   66
 18  ω     63.00  88.00   0.50    0.05    --  106.94 -95.00  30.00   50
 19  ω     44.00  89.00   0.50    0.05    --  106.94 -95.00  90.00   90
 20  ω     58.00  92.00   0.50    0.05    --  106.94 -95.00 150.00   68
 21  ω    -14.00  27.00   0.50    0.05    --  -43.18  38.00   0.00   82
 22  ω     -7.00  33.00   0.50    0.05    --  -43.18  38.00  30.00   80
 23  ω    -62.00  24.00   0.50    0.05    --  -43.18  77.00  60.00  172
 24  ω     -3.00  31.00   0.50    0.05    --  -43.18  38.00 -30.00   68
 25  ω    -41.00  31.00   0.50    0.05    --  -43.18  57.00 -60.00  144
 26  ω    -85.00 -20.00   0.50    0.05    --  -43.18 130.00 -97.00  130
 27  ω    -77.00 -51.00   0.50    0.05    -- -103.00 130.00 -97.00   52
 28  ω    -96.00 -40.00   0.50    0.05    -- -103.00 114.00 -61.90  112
 29  ω    -96.00 -71.00   0.50    0.05    -- -103.00 114.00-161.15   50
 30  ω    -97.00 -33.00   0.50    0.05    -- -103.00 114.00 -35.40  128
 31  ω    -68.00 -42.00   0.50    0.05    -- -103.00 114.00-161.15   52
 32  ω    -97.00 -32.00   0.50    0.05    -- -103.00 114.00  55.29  130
 33  ω    -63.00 -31.00   0.50    0.05    -- -103.00 126.00  60.00   64
 34  ω   -101.00 -70.00   0.50    0.05    -- -103.00 126.00  60.00   62
 35  ω    -93.00 -66.00   0.50    0.05    -- -103.00 102.00 -52.46   54
 36  ω    -93.00 -29.00   0.50    0.05    -- -103.00 102.00 -85.36  128
 37  ω    -84.00 -31.00   0.50    0.05    -- -103.00 114.00-169.41  106
 38  ω    -64.00 -37.00   0.50    0.05    -- -103.00  77.00 -90.00   54
 39  ω    -89.00 -32.00   0.50    0.05    -- -103.00 106.00  -8.29  114
 40  ω    -91.00 -65.00   0.50    0.05    -- -103.00 101.00  54.20   52
 41  ω    -97.00 -72.00   0.50    0.05    -- -103.00 114.00 150.60   50
 42  ω   -131.00 -92.00   0.50    0.05    -- -103.00 -15.00  30.00   78
 43  ω   -122.00 -88.00   0.50    0.05    -- -103.00 -15.00   0.00   68
 44  ω   -133.00 -89.00   0.50    0.05    -- -103.00 -15.00 -60.00   88
 45  ω   -131.00 -92.00   0.50    0.05    -- -103.00 -15.00-120.00   78
 46  ω   -129.00 -99.00   0.50    0.05    -- -103.00 -15.00-150.00   60
 47  ω   -118.00 -79.00   0.50    0.05    --  -43.18 -38.00-120.00   78
 48  ω   -134.00-109.00   0.50    0.05    -- -103.00-130.00-169.00   50
 49  ω   -169.00-114.00   0.50    0.05    -- -103.00 -95.00  60.00  110
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1091347000
_diffrn_orient_matrix_UB_12      0.0060575000
_diffrn_orient_matrix_UB_13      -0.0605511000
_diffrn_orient_matrix_UB_21      0.0768356000
_diffrn_orient_matrix_UB_22      0.0613609000
_diffrn_orient_matrix_UB_23      -0.0644346000
_diffrn_orient_matrix_UB_31      0.1071433000
_diffrn_orient_matrix_UB_32      -0.1429277000
_diffrn_orient_matrix_UB_33      -0.0035237000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                6772
_reflns_number_total             6892
_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 1.171.43.143a (Rigaku OD, 2024)'
_computing_data_collection       
'CrysAlisPro system (CCD 43.143a 64-bit (release 25-10-2024))'
_computing_data_reduction        'CrysAlisPro 1.171.43.143a (Rigaku OD, 2024)'
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_refine_diff_density_max         0.424
_refine_diff_density_min         -0.434
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     525
_refine_ls_number_reflns         6892
_refine_ls_number_restraints     18
_refine_ls_R_factor_all          0.0416
_refine_ls_R_factor_gt           0.0407
_refine_ls_restrained_S_all      1.084
_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)+(0.0443P)²+1.1666P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1018
_refine_ls_wR_factor_ref         0.1024
_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. Rigid body (RIGU) restrains
 C35, C37, C36, C34
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.008
3.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C10(H10), C17(H17), C18(H18), C19(H19), C20(H20),
 C21(H21), C26(H26), C27(H27), C32(H32), C39(H39), C40(H40), C41(H41), C42(H42),
  C43(H43), C46(H46)
3.b Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C23(H23A,H23B,H23C), C36(H36A,H36B,H36C), C45(H45A,H45B,
 H45C)
;
_atom_sites_solution_hydrogens   mixed
_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
F1 F 1.25133(10) -0.57271(9) 0.68983(5) 0.0299(2) Uani 1 1 d . . . . .
F2 F 0.87056(11) -0.23885(10) 0.33887(6) 0.0312(2) Uani 1 1 d . . . . .
F3 F 0.85875(10) -0.05404(10) 0.26109(5) 0.0299(2) Uani 1 1 d . . . . .
F4 F 1.05130(9) -0.18165(9) 0.33998(5) 0.0250(2) Uani 1 1 d . . . . .
N1 N 0.86992(13) -0.11993(12) 0.59677(7) 0.0193(2) Uani 1 1 d . . . . .
C1 C 0.97854(16) -0.25090(15) 0.51609(8) 0.0190(3) Uani 1 1 d . . . . .
C2 C 1.07397(16) -0.37123(15) 0.49994(9) 0.0215(3) Uani 1 1 d . . . . .
H2 H 1.076406 -0.378558 0.448874 0.026 Uiso 1 1 calc R U . . .
C3 C 1.16461(17) -0.47925(15) 0.55901(9) 0.0238(3) Uani 1 1 d . . . . .
H3 H 1.230292 -0.561497 0.548962 0.029 Uiso 1 1 calc R U . . .
C4 C 1.15862(16) -0.46624(15) 0.63341(9) 0.0233(3) Uani 1 1 d . . . . .
C5 C 1.06556(16) -0.35229(15) 0.65342(9) 0.0225(3) Uani 1 1 d . . . . .
H5 H 1.063362 -0.347135 0.704926 0.027 Uiso 1 1 calc R U . . .
C6 C 0.97397(16) -0.24403(15) 0.59278(8) 0.0192(3) Uani 1 1 d . . . . .
C7 C 0.80404(15) -0.04346(15) 0.52311(8) 0.0180(3) Uani 1 1 d . . . . .
C8 C 0.87266(15) -0.12032(14) 0.47071(8) 0.0179(3) Uani 1 1 d . . . . .
C9 C 0.83190(15) -0.05897(14) 0.39183(8) 0.0178(3) Uani 1 1 d . . . . .
C10 C 0.72394(15) 0.07149(15) 0.36741(8) 0.0188(3) Uani 1 1 d . . . . .
H10 H 0.700156 0.114386 0.313909 0.023 Uiso 1 1 calc R U . . .
C11 C 0.64816(15) 0.14254(14) 0.42004(8) 0.0182(3) Uani 1 1 d . . . . .
C12 C 0.68600(15) 0.08632(14) 0.49924(8) 0.0182(3) Uani 1 1 d . . . . .
C13 C 0.59880(16) 0.16163(15) 0.55431(8) 0.0203(3) Uani 1 1 d . . . . .
C14 C 0.50575(19) 0.11753(19) 0.59805(10) 0.0290(3) Uani 1 1 d . . . . .
H14A H 0.451(2) 0.168(2) 0.6323(13) 0.040(6) Uiso 1 1 d . . . . .
H14B H 0.499(3) 0.039(3) 0.5957(15) 0.061(7) Uiso 1 1 d . . . . .
C15 C 0.61436(18) 0.28397(16) 0.55662(9) 0.0269(3) Uani 1 1 d . . . . .
H15A H 0.717897 0.260256 0.572072 0.040 Uiso 1 1 calc R U . . .
H15B H 0.549923 0.324324 0.593743 0.040 Uiso 1 1 calc R U . . .
H15C H 0.585626 0.348945 0.505573 0.040 Uiso 1 1 calc R U . . .
C16 C 0.52313(16) 0.27706(14) 0.38675(8) 0.0184(3) Uani 1 1 d . . . . .
C17 C 0.37657(16) 0.30257(15) 0.40361(8) 0.0208(3) Uani 1 1 d . . . . .
H17 H 0.356251 0.235360 0.439784 0.025 Uiso 1 1 calc R U . . .
C18 C 0.26116(16) 0.42547(16) 0.36771(9) 0.0236(3) Uani 1 1 d . . . . .
H18 H 0.161759 0.441689 0.378659 0.028 Uiso 1 1 calc R U . . .
C19 C 0.29024(17) 0.52503(16) 0.31579(9) 0.0248(3) Uani 1 1 d . . . . .
H19 H 0.210947 0.609573 0.291655 0.030 Uiso 1 1 calc R U . . .
C20 C 0.43547(17) 0.50093(15) 0.29912(9) 0.0239(3) Uani 1 1 d . . . . .
H20 H 0.455651 0.569329 0.264020 0.029 Uiso 1 1 calc R U . . .
C21 C 0.55057(16) 0.37726(15) 0.33370(8) 0.0208(3) Uani 1 1 d . . . . .
H21 H 0.649371 0.360405 0.321163 0.025 Uiso 1 1 calc R U . . .
C22 C 0.90175(16) -0.13243(15) 0.33327(8) 0.0206(3) Uani 1 1 d . . . . .
C23 C 0.85841(18) -0.07556(16) 0.66617(9) 0.0246(3) Uani 1 1 d . . . . .
H23A H 0.815585 0.023362 0.652269 0.037 Uiso 1 1 calc R U . . .
H23B H 0.957492 -0.112543 0.692713 0.037 Uiso 1 1 calc R U . . .
H23C H 0.794422 -0.107685 0.700153 0.037 Uiso 1 1 calc R U . . .
F5 F 0.78734(11) 0.14927(9) 0.11114(6) 0.0322(2) Uani 1 1 d . . . . .
F6 F 0.99952(10) 0.64220(10) 0.07831(5) 0.0284(2) Uani 1 1 d . . . . .
F7 F 0.98347(10) 0.77834(10) 0.14477(6) 0.0331(2) Uani 1 1 d . . . . .
F8 F 1.00002(10) 0.58001(9) 0.20168(5) 0.0286(2) Uani 1 1 d . . . . .
N2 N 0.50033(13) 0.61490(12) 0.10629(7) 0.0186(2) Uani 1 1 d . . . . .
C24 C 0.62545(16) 0.49738(14) 0.11113(8) 0.0185(3) Uani 1 1 d . . . . .
C25 C 0.75378(16) 0.51821(14) 0.12083(8) 0.0179(3) Uani 1 1 d . . . . .
C26 C 0.89369(16) 0.41101(15) 0.12671(8) 0.0214(3) Uani 1 1 d . . . . .
H26 H 0.981066 0.423281 0.132924 0.026 Uiso 1 1 calc R U . . .
C27 C 0.90415(17) 0.28708(15) 0.12344(9) 0.0247(3) Uani 1 1 d . . . . .
H27 H 0.998439 0.213301 0.127252 0.030 Uiso 1 1 calc R U . . .
C28 C 0.77416(18) 0.27224(15) 0.11446(9) 0.0236(3) Uani 1 1 d . . . . .
C29 C 0.54396(15) 0.71336(14) 0.11430(8) 0.0161(3) Uani 1 1 d . . . . .
C30 C 0.70171(15) 0.65649(14) 0.12266(8) 0.0164(3) Uani 1 1 d . . . . .
C31 C 0.77133(15) 0.73806(14) 0.13184(8) 0.0175(3) Uani 1 1 d . . . . .
C32 C 0.68614(15) 0.86820(14) 0.13412(8) 0.0177(3) Uani 1 1 d . . . . .
H32 H 0.733664 0.922689 0.140428 0.021 Uiso 1 1 calc R U . . .
C33 C 0.53042(15) 0.92264(14) 0.12734(8) 0.0167(3) Uani 1 1 d . . . . .
C34 C 0.45552(15) 0.84605(14) 0.11733(8) 0.0172(3) Uani 1 1 d . . . . .
C35 C 0.28949(16) 0.90296(14) 0.11696(9) 0.0214(3) Uani 1 1 d . . . . .
C36 C 0.22982(18) 0.89471(17) 0.18946(9) 0.0268(3) Uani 1 1 d . . . . .
H36A H 0.267660 0.799854 0.219655 0.040 Uiso 1 1 calc R U . . .
H36B H 0.121194 0.933473 0.182038 0.040 Uiso 1 1 calc R U . . .
H36C H 0.259375 0.945114 0.216800 0.040 Uiso 1 1 calc R U . . .
C37 C 0.19860(19) 0.96535(18) 0.04731(10) 0.0303(4) Uani 1 1 d . . . . .
H37A H 0.240(3) 0.947(3) 0.0045(16) 0.062(8) Uiso 1 1 d . . . . .
H37B H 0.094(3) 0.994(3) 0.0499(14) 0.056(7) Uiso 1 1 d . . . . .
C38 C 0.44847(15) 1.06194(14) 0.13530(8) 0.0167(3) Uani 1 1 d . . . . .
C39 C 0.35430(16) 1.16786(15) 0.07548(8) 0.0211(3) Uani 1 1 d . . . . .
H39 H 0.342738 1.152573 0.027563 0.025 Uiso 1 1 calc R U . . .
C40 C 0.27733(17) 1.29557(15) 0.08554(9) 0.0242(3) Uani 1 1 d . . . . .
H40 H 0.213155 1.367559 0.044530 0.029 Uiso 1 1 calc R U . . .
C41 C 0.29380(16) 1.31853(15) 0.15541(9) 0.0231(3) Uani 1 1 d . . . . .
H41 H 0.238610 1.405510 0.162643 0.028 Uiso 1 1 calc R U . . .
C42 C 0.39044(17) 1.21495(16) 0.21451(9) 0.0241(3) Uani 1 1 d . . . . .
H42 H 0.403510 1.231099 0.261953 0.029 Uiso 1 1 calc R U . . .
C43 C 0.46793(16) 1.08780(15) 0.20422(9) 0.0215(3) Uani 1 1 d . . . . .
H43 H 0.535325 1.017110 0.244624 0.026 Uiso 1 1 calc R U . . .
C44 C 0.93696(16) 0.68533(15) 0.13924(9) 0.0216(3) Uani 1 1 d . . . . .
C45 C 0.35022(16) 0.62696(16) 0.09412(10) 0.0242(3) Uani 1 1 d . . . . .
H45A H 0.301020 0.630341 0.141864 0.036 Uiso 1 1 calc R U . . .
H45B H 0.355293 0.548733 0.078715 0.036 Uiso 1 1 calc R U . . .
H45C H 0.293587 0.709887 0.053605 0.036 Uiso 1 1 calc R U . . .
C46 C 0.63367(17) 0.37257(15) 0.10799(9) 0.0224(3) Uani 1 1 d . . . . .
H46 H 0.547545 0.358412 0.101798 0.027 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C4 1.3546(17) . ?
F2 C22 1.3434(17) . ?
F3 C22 1.3373(17) . ?
F4 C22 1.3494(17) . ?
N1 C6 1.3742(19) . ?
N1 C7 1.3918(18) . ?
N1 C23 1.4591(19) . ?
C1 C2 1.400(2) . ?
C1 C6 1.411(2) . ?
C1 C8 1.445(2) . ?
C2 H2 0.9500 . ?
C2 C3 1.382(2) . ?
C3 H3 0.9500 . ?
C3 C4 1.392(2) . ?
C4 C5 1.373(2) . ?
C5 H5 0.9500 . ?
C5 C6 1.402(2) . ?
C7 C8 1.423(2) . ?
C7 C12 1.409(2) . ?
C8 C9 1.404(2) . ?
C9 C10 1.377(2) . ?
C9 C22 1.496(2) . ?
C10 H10 0.9500 . ?
C10 C11 1.406(2) . ?
C11 C12 1.400(2) . ?
C11 C16 1.4888(19) . ?
C12 C13 1.500(2) . ?
C13 C14 1.361(2) . ?
C13 C15 1.469(2) . ?
C14 H14A 0.95(2) . ?
C14 H14B 0.93(3) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 C17 1.401(2) . ?
C16 C21 1.394(2) . ?
C17 H17 0.9500 . ?
C17 C18 1.385(2) . ?
C18 H18 0.9500 . ?
C18 C19 1.388(2) . ?
C19 H19 0.9500 . ?
C19 C20 1.390(2) . ?
C20 H20 0.9500 . ?
C20 C21 1.383(2) . ?
C21 H21 0.9500 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
F5 C28 1.3619(17) . ?
F6 C44 1.3526(17) . ?
F7 C44 1.3421(17) . ?
F8 C44 1.3439(18) . ?
N2 C24 1.3756(19) . ?
N2 C29 1.3961(18) . ?
N2 C45 1.4600(18) . ?
C24 C25 1.415(2) . ?
C24 C46 1.399(2) . ?
C25 C26 1.398(2) . ?
C25 C30 1.4404(19) . ?
C26 H26 0.9500 . ?
C26 C27 1.382(2) . ?
C27 H27 0.9500 . ?
C27 C28 1.391(2) . ?
C28 C46 1.369(2) . ?
C29 C30 1.4210(19) . ?
C29 C34 1.405(2) . ?
C30 C31 1.409(2) . ?
C31 C32 1.372(2) . ?
C31 C44 1.4960(19) . ?
C32 H32 0.9500 . ?
C32 C33 1.4029(19) . ?
C33 C34 1.4049(19) . ?
C33 C38 1.4889(19) . ?
C34 C35 1.5000(19) . ?
C35 C36 1.418(2) . ?
C35 C37 1.409(2) . ?
C36 H36A 0.9800 . ?
C36 H36B 0.9800 . ?
C36 H36C 0.9800 . ?
C37 H37A 0.90(3) . ?
C37 H37B 0.96(3) . ?
C38 C39 1.392(2) . ?
C38 C43 1.395(2) . ?
C39 H39 0.9500 . ?
C39 C40 1.386(2) . ?
C40 H40 0.9500 . ?
C40 C41 1.388(2) . ?
C41 H41 0.9500 . ?
C41 C42 1.383(2) . ?
C42 H42 0.9500 . ?
C42 C43 1.383(2) . ?
C43 H43 0.9500 . ?
C45 H45A 0.9800 . ?
C45 H45B 0.9800 . ?
C45 H45C 0.9800 . ?
C46 H46 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
C6 N1 C7 108.48(12) . . ?
C6 N1 C23 122.13(12) . . ?
C7 N1 C23 128.41(12) . . ?
C2 C1 C6 119.17(13) . . ?
C2 C1 C8 134.79(14) . . ?
C6 C1 C8 106.04(13) . . ?
C1 C2 H2 120.3 . . ?
C3 C2 C1 119.34(14) . . ?
C3 C2 H2 120.3 . . ?
C2 C3 H3 120.4 . . ?
C2 C3 C4 119.27(14) . . ?
C4 C3 H3 120.4 . . ?
F1 C4 C3 117.94(14) . . ?
F1 C4 C5 117.70(14) . . ?
C5 C4 C3 124.36(14) . . ?
C4 C5 H5 122.2 . . ?
C4 C5 C6 115.53(14) . . ?
C6 C5 H5 122.2 . . ?
N1 C6 C1 110.12(13) . . ?
N1 C6 C5 127.58(14) . . ?
C5 C6 C1 122.30(14) . . ?
N1 C7 C8 108.61(12) . . ?
N1 C7 C12 129.18(13) . . ?
C12 C7 C8 122.18(13) . . ?
C7 C8 C1 106.66(12) . . ?
C9 C8 C1 134.70(13) . . ?
C9 C8 C7 118.60(13) . . ?
C8 C9 C22 121.61(13) . . ?
C10 C9 C8 119.50(13) . . ?
C10 C9 C22 118.89(13) . . ?
C9 C10 H10 119.3 . . ?
C9 C10 C11 121.36(13) . . ?
C11 C10 H10 119.3 . . ?
C10 C11 C16 116.16(12) . . ?
C12 C11 C10 121.20(13) . . ?
C12 C11 C16 122.60(13) . . ?
C7 C12 C13 123.12(13) . . ?
C11 C12 C7 116.75(13) . . ?
C11 C12 C13 120.09(13) . . ?
C14 C13 C12 119.50(14) . . ?
C14 C13 C15 122.63(14) . . ?
C15 C13 C12 117.84(13) . . ?
C13 C14 H14A 117.7(13) . . ?
C13 C14 H14B 120.8(16) . . ?
H14A C14 H14B 121(2) . . ?
C13 C15 H15A 109.5 . . ?
C13 C15 H15B 109.5 . . ?
C13 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C17 C16 C11 121.43(13) . . ?
C21 C16 C11 119.47(13) . . ?
C21 C16 C17 118.97(13) . . ?
C16 C17 H17 119.9 . . ?
C18 C17 C16 120.22(14) . . ?
C18 C17 H17 119.9 . . ?
C17 C18 H18 119.9 . . ?
C17 C18 C19 120.21(14) . . ?
C19 C18 H18 119.9 . . ?
C18 C19 H19 120.0 . . ?
C18 C19 C20 119.95(14) . . ?
C20 C19 H19 120.0 . . ?
C19 C20 H20 120.0 . . ?
C21 C20 C19 119.92(14) . . ?
C21 C20 H20 120.0 . . ?
C16 C21 H21 119.6 . . ?
C20 C21 C16 120.70(14) . . ?
C20 C21 H21 119.6 . . ?
F2 C22 F4 106.05(11) . . ?
F2 C22 C9 112.65(12) . . ?
F3 C22 F2 106.57(12) . . ?
F3 C22 F4 105.78(11) . . ?
F3 C22 C9 112.98(12) . . ?
F4 C22 C9 112.27(12) . . ?
N1 C23 H23A 109.5 . . ?
N1 C23 H23B 109.5 . . ?
N1 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C24 N2 C29 108.63(11) . . ?
C24 N2 C45 122.89(12) . . ?
C29 N2 C45 128.48(12) . . ?
N2 C24 C25 109.70(12) . . ?
N2 C24 C46 128.06(13) . . ?
C46 C24 C25 122.24(13) . . ?
C24 C25 C30 106.30(12) . . ?
C26 C25 C24 119.03(13) . . ?
C26 C25 C30 134.67(14) . . ?
C25 C26 H26 120.2 . . ?
C27 C26 C25 119.60(14) . . ?
C27 C26 H26 120.2 . . ?
C26 C27 H27 120.6 . . ?
C26 C27 C28 118.83(14) . . ?
C28 C27 H27 120.6 . . ?
F5 C28 C27 117.74(14) . . ?
F5 C28 C46 117.44(14) . . ?
C46 C28 C27 124.81(14) . . ?
N2 C29 C30 108.42(12) . . ?
N2 C29 C34 129.14(13) . . ?
C34 C29 C30 122.40(12) . . ?
C29 C30 C25 106.93(12) . . ?
C31 C30 C25 134.56(13) . . ?
C31 C30 C29 118.49(12) . . ?
C30 C31 C44 121.18(13) . . ?
C32 C31 C30 119.61(13) . . ?
C32 C31 C44 119.21(13) . . ?
C31 C32 H32 119.3 . . ?
C31 C32 C33 121.49(13) . . ?
C33 C32 H32 119.3 . . ?
C32 C33 C34 121.17(13) . . ?
C32 C33 C38 117.23(12) . . ?
C34 C33 C38 121.53(12) . . ?
C29 C34 C35 123.14(12) . . ?
C33 C34 C29 116.82(12) . . ?
C33 C34 C35 119.84(12) . . ?
C36 C35 C34 116.83(13) . . ?
C37 C35 C34 120.88(14) . . ?
C37 C35 C36 122.26(14) . . ?
C35 C36 H36A 109.5 . . ?
C35 C36 H36B 109.5 . . ?
C35 C36 H36C 109.5 . . ?
H36A C36 H36B 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?
C35 C37 H37A 117.7(17) . . ?
C35 C37 H37B 117.8(15) . . ?
H37A C37 H37B 120(2) . . ?
C39 C38 C33 121.86(13) . . ?
C39 C38 C43 118.89(13) . . ?
C43 C38 C33 119.24(13) . . ?
C38 C39 H39 119.9 . . ?
C40 C39 C38 120.24(14) . . ?
C40 C39 H39 119.9 . . ?
C39 C40 H40 119.9 . . ?
C39 C40 C41 120.14(14) . . ?
C41 C40 H40 119.9 . . ?
C40 C41 H41 120.0 . . ?
C42 C41 C40 120.10(14) . . ?
C42 C41 H41 120.0 . . ?
C41 C42 H42 120.2 . . ?
C43 C42 C41 119.68(14) . . ?
C43 C42 H42 120.2 . . ?
C38 C43 H43 119.6 . . ?
C42 C43 C38 120.87(14) . . ?
C42 C43 H43 119.6 . . ?
F6 C44 C31 112.40(12) . . ?
F7 C44 F6 106.01(12) . . ?
F7 C44 F8 106.11(12) . . ?
F7 C44 C31 112.96(12) . . ?
F8 C44 F6 106.29(11) . . ?
F8 C44 C31 112.54(12) . . ?
N2 C45 H45A 109.5 . . ?
N2 C45 H45B 109.5 . . ?
N2 C45 H45C 109.5 . . ?
H45A C45 H45B 109.5 . . ?
H45A C45 H45C 109.5 . . ?
H45B C45 H45C 109.5 . . ?
C24 C46 H46 122.3 . . ?
C28 C46 C24 115.49(14) . . ?
C28 C46 H46 122.3 . . ?

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 C4 C5 C6 178.77(12) . . . . ?
N1 C7 C8 C1 3.09(15) . . . . ?
N1 C7 C8 C9 -174.99(12) . . . . ?
N1 C7 C12 C11 176.24(13) . . . . ?
N1 C7 C12 C13 -6.0(2) . . . . ?
C1 C2 C3 C4 0.3(2) . . . . ?
C1 C8 C9 C10 -179.52(14) . . . . ?
C1 C8 C9 C22 1.2(2) . . . . ?
C2 C1 C6 N1 -177.70(12) . . . . ?
C2 C1 C6 C5 2.2(2) . . . . ?
C2 C1 C8 C7 176.36(16) . . . . ?
C2 C1 C8 C9 -6.0(3) . . . . ?
C2 C3 C4 F1 -178.44(13) . . . . ?
C2 C3 C4 C5 1.1(2) . . . . ?
C3 C4 C5 C6 -0.8(2) . . . . ?
C4 C5 C6 N1 179.02(14) . . . . ?
C4 C5 C6 C1 -0.9(2) . . . . ?
C6 N1 C7 C8 -2.10(15) . . . . ?
C6 N1 C7 C12 175.82(14) . . . . ?
C6 C1 C2 C3 -1.8(2) . . . . ?
C6 C1 C8 C7 -2.88(15) . . . . ?
C6 C1 C8 C9 174.75(15) . . . . ?
C7 N1 C6 C1 0.23(16) . . . . ?
C7 N1 C6 C5 -179.68(14) . . . . ?
C7 C8 C9 C10 -2.1(2) . . . . ?
C7 C8 C9 C22 178.61(12) . . . . ?
C7 C12 C13 C14 -69.8(2) . . . . ?
C7 C12 C13 C15 112.22(16) . . . . ?
C8 C1 C2 C3 178.99(15) . . . . ?
C8 C1 C6 N1 1.68(15) . . . . ?
C8 C1 C6 C5 -178.41(13) . . . . ?
C8 C7 C12 C11 -6.1(2) . . . . ?
C8 C7 C12 C13 171.69(13) . . . . ?
C8 C9 C10 C11 -3.2(2) . . . . ?
C8 C9 C22 F2 64.84(17) . . . . ?
C8 C9 C22 F3 -174.32(12) . . . . ?
C8 C9 C22 F4 -54.80(18) . . . . ?
C9 C10 C11 C12 4.0(2) . . . . ?
C9 C10 C11 C16 -173.71(13) . . . . ?
C10 C9 C22 F2 -114.46(14) . . . . ?
C10 C9 C22 F3 6.38(19) . . . . ?
C10 C9 C22 F4 125.90(14) . . . . ?
C10 C11 C12 C7 0.7(2) . . . . ?
C10 C11 C12 C13 -177.19(13) . . . . ?
C10 C11 C16 C17 116.28(15) . . . . ?
C10 C11 C16 C21 -59.40(18) . . . . ?
C11 C12 C13 C14 107.89(17) . . . . ?
C11 C12 C13 C15 -70.07(18) . . . . ?
C11 C16 C17 C18 -175.47(13) . . . . ?
C11 C16 C21 C20 176.91(13) . . . . ?
C12 C7 C8 C1 -175.00(13) . . . . ?
C12 C7 C8 C9 6.9(2) . . . . ?
C12 C11 C16 C17 -61.39(19) . . . . ?
C12 C11 C16 C21 122.93(15) . . . . ?
C16 C11 C12 C7 178.22(12) . . . . ?
C16 C11 C12 C13 0.4(2) . . . . ?
C16 C17 C18 C19 -1.1(2) . . . . ?
C17 C16 C21 C20 1.1(2) . . . . ?
C17 C18 C19 C20 0.7(2) . . . . ?
C18 C19 C20 C21 0.7(2) . . . . ?
C19 C20 C21 C16 -1.6(2) . . . . ?
C21 C16 C17 C18 0.2(2) . . . . ?
C22 C9 C10 C11 176.12(13) . . . . ?
C23 N1 C6 C1 -169.33(13) . . . . ?
C23 N1 C6 C5 10.8(2) . . . . ?
C23 N1 C7 C8 166.60(13) . . . . ?
C23 N1 C7 C12 -15.5(2) . . . . ?
F5 C28 C46 C24 -179.53(13) . . . . ?
N2 C24 C25 C26 -179.73(13) . . . . ?
N2 C24 C25 C30 0.60(15) . . . . ?
N2 C24 C46 C28 -179.92(14) . . . . ?
N2 C29 C30 C25 -0.97(15) . . . . ?
N2 C29 C30 C31 -179.87(12) . . . . ?
N2 C29 C34 C33 178.74(13) . . . . ?
N2 C29 C34 C35 3.9(2) . . . . ?
C24 N2 C29 C30 1.36(15) . . . . ?
C24 N2 C29 C34 -176.23(14) . . . . ?
C24 C25 C26 C27 -0.4(2) . . . . ?
C24 C25 C30 C29 0.23(15) . . . . ?
C24 C25 C30 C31 178.87(15) . . . . ?
C25 C24 C46 C28 -0.4(2) . . . . ?
C25 C26 C27 C28 -0.1(2) . . . . ?
C25 C30 C31 C32 -177.15(14) . . . . ?
C25 C30 C31 C44 2.8(2) . . . . ?
C26 C25 C30 C29 -179.36(16) . . . . ?
C26 C25 C30 C31 -0.7(3) . . . . ?
C26 C27 C28 F5 179.79(13) . . . . ?
C26 C27 C28 C46 0.4(2) . . . . ?
C27 C28 C46 C24 -0.2(2) . . . . ?
C29 N2 C24 C25 -1.22(16) . . . . ?
C29 N2 C24 C46 178.35(14) . . . . ?
C29 C30 C31 C32 1.4(2) . . . . ?
C29 C30 C31 C44 -178.67(13) . . . . ?
C29 C34 C35 C36 94.09(17) . . . . ?
C29 C34 C35 C37 -87.96(19) . . . . ?
C30 C25 C26 C27 179.16(15) . . . . ?
C30 C29 C34 C33 1.4(2) . . . . ?
C30 C29 C34 C35 -173.35(13) . . . . ?
C30 C31 C32 C33 -0.1(2) . . . . ?
C30 C31 C44 F6 57.85(18) . . . . ?
C30 C31 C44 F7 177.75(13) . . . . ?
C30 C31 C44 F8 -62.12(17) . . . . ?
C31 C32 C33 C34 -0.5(2) . . . . ?
C31 C32 C33 C38 176.38(13) . . . . ?
C32 C31 C44 F6 -122.19(14) . . . . ?
C32 C31 C44 F7 -2.29(19) . . . . ?
C32 C31 C44 F8 117.84(14) . . . . ?
C32 C33 C34 C29 -0.1(2) . . . . ?
C32 C33 C34 C35 174.83(13) . . . . ?
C32 C33 C38 C39 117.65(15) . . . . ?
C32 C33 C38 C43 -61.45(18) . . . . ?
C33 C34 C35 C36 -80.55(17) . . . . ?
C33 C34 C35 C37 97.40(17) . . . . ?
C33 C38 C39 C40 178.58(13) . . . . ?
C33 C38 C43 C42 -178.10(13) . . . . ?
C34 C29 C30 C25 176.81(12) . . . . ?
C34 C29 C30 C31 -2.1(2) . . . . ?
C34 C33 C38 C39 -65.47(19) . . . . ?
C34 C33 C38 C43 115.43(15) . . . . ?
C38 C33 C34 C29 -176.90(12) . . . . ?
C38 C33 C34 C35 -1.9(2) . . . . ?
C38 C39 C40 C41 0.0(2) . . . . ?
C39 C38 C43 C42 2.8(2) . . . . ?
C39 C40 C41 C42 1.9(2) . . . . ?
C40 C41 C42 C43 -1.5(2) . . . . ?
C41 C42 C43 C38 -0.9(2) . . . . ?
C43 C38 C39 C40 -2.3(2) . . . . ?
C44 C31 C32 C33 179.91(13) . . . . ?
C45 N2 C24 C25 178.35(13) . . . . ?
C45 N2 C24 C46 -2.1(2) . . . . ?
C45 N2 C29 C30 -178.19(13) . . . . ?
C45 N2 C29 C34 4.2(2) . . . . ?
C46 C24 C25 C26 0.7(2) . . . . ?
C46 C24 C25 C30 -179.00(13) . . . . ?

_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 1.515
_oxdiff_exptl_absorpt_empirical_full_min 0.553
####################################################################### 
# 
# 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_97549_cf3
_database_code_depnum_ccdc_archive 'CCDC 2449182'
loop_
_audit_author_name
_audit_author_address
'Shizhou Yang'
;Chongqing University of Technology
China
;
_audit_update_record             
;
2025-05-07 deposited with the CCDC.	2026-02-26 downloaded from the CCDC.
;
_audit_creation_date             2024-11-02
_audit_creation_method           
;
Olex2 1.5-beta
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H18 F3 N, C3 H7'
_chemical_formula_sum            'C26 H25 F3 N'
_chemical_formula_weight         408.47
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H O N  F'
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'

_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                   9.0837(2)
_cell_length_b                   10.11921(18)
_cell_length_c                   12.4621(3)
_cell_angle_alpha                72.752(2)
_cell_angle_beta                 75.888(2)
_cell_angle_gamma                86.8218(17)
_cell_volume                     1060.80(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    10062
_cell_measurement_temperature    170.00(10)
_cell_measurement_theta_max      72.4730
_cell_measurement_theta_min      3.8110
_shelx_estimated_absorpt_T_max   0.928
_shelx_estimated_absorpt_T_min   0.908
_exptl_absorpt_coefficient_mu    0.758
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.85622
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.121a (Rigaku Oxford Diffraction, 2024)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.279
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             430
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0469
_diffrn_reflns_av_unetI/netI     0.0202
_diffrn_reflns_Laue_measured_fraction_full 0.966
_diffrn_reflns_Laue_measured_fraction_max 0.931
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            14404
_diffrn_reflns_point_group_measured_fraction_full 0.966
_diffrn_reflns_point_group_measured_fraction_max 0.931
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.863
_diffrn_reflns_theta_min         3.824
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      170.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            'HyPix-Arc 150'
_diffrn_measured_fraction_theta_full 0.966
_diffrn_measured_fraction_theta_max 0.931
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     59.00  89.00   0.50    0.05    --   62.21  15.00 150.00   60
  2  ω     56.00 102.00   0.50    0.05    --   62.21  15.00 120.00   92
  3  ω     62.00  97.00   0.50    0.05    --   62.21  15.00   0.00   70
  4  ω     58.00  83.00   0.50    0.05    --   62.21  15.00 -30.00   50
  5  ω     58.00 102.00   0.50    0.05    --   62.21  15.00 -90.00   88
  6  ω     55.00 103.00   0.50    0.05    --   62.21  15.00-120.00   96
  7  ω     72.00  98.00   0.50    0.05    --   62.21  15.00-150.00   52
  8  ω     69.00 102.00   0.50    0.05    --   62.21  15.00-180.00   66
  9  ω     57.00  82.00   0.50    0.05    --   62.21  15.00  30.00   50
 10  ω     67.00 115.00   0.50    0.05    --   74.33  15.00  60.00   96
 11  ω     69.00  94.00   0.50    0.05    --   71.27  15.00 120.00   50
 12  ω     65.00 107.00   0.50    0.05    --   71.27  15.00 150.00   84
 13  ω     67.00  92.00   0.50    0.05    --   74.33  15.00   0.00   50
 14  ω     76.00 101.00   0.50    0.05    --   74.33  15.00 -30.00   50
 15  ω     67.00 112.00   0.50    0.05    --   74.33  15.00 -60.00   90
 16  ω     74.00  99.00   0.50    0.05    --   74.33  15.00 -90.00   50
 17  ω     68.00  93.00   0.50    0.05    --   74.33  15.00-120.00   50
 18  ω     70.00 102.00   0.50    0.05    --   74.33  15.00-150.00   64
 19  ω     76.00 101.00   0.50    0.05    --   74.33  15.00-180.00   50
 20  ω     69.00  97.00   0.50    0.05    --   74.33  15.00  30.00   56
 21  ω     80.00 105.00   0.50    0.05    --   74.33  15.00  90.00   50
 22  ω     39.00  64.00   0.50    0.05    --   74.33-116.00 122.00   50
 23  ω     27.00  53.00   0.50    0.05    --   62.21-125.00 120.00   52
 24  ω     26.00  78.00   0.50    0.05    --   62.21-125.00  90.00  104
 25  ω     25.00  78.00   0.50    0.05    --   62.21-125.00  60.00  106
 26  ω     26.00  67.00   0.50    0.05    --   62.21-125.00   0.00   82
 27  ω     32.00  58.00   0.50    0.05    --   62.21-125.00 150.00   52
 28  ω     26.00  56.00   0.50    0.05    --   62.21-125.00 -30.00   60
 29  ω     49.00  78.00   0.50    0.05    --   62.21-125.00  30.00   58
 30  ω     35.00  87.00   0.50    0.05    --   71.27-125.00  30.00  104
 31  ω     41.00  83.00   0.50    0.05    --   71.27-125.00 -30.00   84
 32  ω     26.00  78.00   0.50    0.05    --   62.21-125.00 -60.00  104
 33  ω     46.00  74.00   0.50    0.05    --   62.21-125.00-120.00   56
 34  ω     49.00  87.00   0.50    0.05    --   71.27-125.00 -90.00   76
 35  ω     62.00  87.00   0.50    0.05    --   71.27-125.00-120.00   50
 36  ω     57.00  85.00   0.50    0.05    --   71.27-125.00-180.00   56
 37  ω     29.00  78.00   0.50    0.05    --   62.21-125.00-180.00   98
 38  ω     39.00  90.00   0.50    0.05    --   74.33-125.00-120.00  102
 39  ω     63.00  88.00   0.50    0.05    --   74.33-125.00-180.00   50
 40  ω     51.00  90.00   0.50    0.05    --   74.33-125.00 -60.00   78
 41  ω     46.00  90.00   0.50    0.05    --   74.33-125.00   0.00   88
 42  ω     46.00  90.00   0.50    0.05    --   74.33-125.00  60.00   88
 43  ω     44.00  70.00   0.50    0.05    --   74.33-125.00  90.00   52
 44  ω     58.00  89.00   0.50    0.05    --   74.33-125.00 150.00   62
 45  ω     48.00  81.00   0.50    0.05    --   71.27-116.00 122.00   66
 46  ω     53.00  90.00   0.50    0.05    --   74.33-125.00 120.00   74
 47  ω     65.00  90.00   0.50    0.05    --   74.33-125.00 -30.00   50
 48  ω     64.00  89.00   0.50    0.05    --   74.33-125.00 -90.00   50
 49  ω     46.00  90.00   0.50    0.05    --   74.33-125.00-150.00   88
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom system, HyPix-Arc 150'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0837402000
_diffrn_orient_matrix_UB_12      0.0563240000
_diffrn_orient_matrix_UB_13      -0.1282636000
_diffrn_orient_matrix_UB_21      0.1492517000
_diffrn_orient_matrix_UB_22      -0.0611044000
_diffrn_orient_matrix_UB_23      0.0296926000
_diffrn_orient_matrix_UB_31      -0.0360915000
_diffrn_orient_matrix_UB_32      -0.1360657000
_diffrn_orient_matrix_UB_33      -0.0207853000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3621
_reflns_number_total             3950
_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 1.171.43.121a (Rigaku OD, 2024)'
_computing_data_collection       
'CrysAlisPro system (CCD 43.121a 64-bit (release 24-04-2024))'
_computing_data_reduction        'CrysAlisPro 1.171.43.121a (Rigaku OD, 2024)'
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_refine_diff_density_max         0.384
_refine_diff_density_min         -0.446
_refine_diff_density_rms         0.059
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     292
_refine_ls_number_reflns         3950
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0574
_refine_ls_R_factor_gt           0.0546
_refine_ls_restrained_S_all      1.036
_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)+(0.1043P)²+0.4109P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1610
_refine_ls_wR_factor_ref         0.1640
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All C(H,H,H,H,H,H) groups
2. Others
 Sof(H24D)=Sof(H24E)=Sof(H24F)=Sof(H26C)=Sof(H26D)=Sof(C27)=Sof(H27A)=
 Sof(H27B)=1-FVAR(1)
 Sof(H24A)=Sof(H24B)=Sof(H24C)=Sof(C25)=Sof(H25A)=Sof(H25B)=Sof(H26A)=
 Sof(H26B)=FVAR(1)
3.a Secondary CH2 refined with riding coordinates:
 C25(H25A,H25B), C26(H26C,H26D), C26(H26A,H26B), C27(H27A,H27B)
3.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C10(H10), C17(H17), C18(H18), C19(H19),
 C20(H20), C21(H21)
3.c Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C22(H22A,H22B,H22C), C24(H24A,H24B,H24C), C24(H24D,H24E,
 H24F)
;
_atom_sites_solution_hydrogens   mixed
_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
F1 F 0.12220(12) 0.32016(12) 0.47886(9) 0.0476(3) Uani 1 1 d . . . . .
F2 F 0.14450(12) 0.54068(13) 0.41217(11) 0.0546(4) Uani 1 1 d . . . . .
F3 F 0.03732(11) 0.42766(13) 0.33119(10) 0.0497(3) Uani 1 1 d . . . . .
N1 N 0.49265(15) 0.15842(15) 0.17017(12) 0.0335(3) Uani 1 1 d . . . . .
C1 C 0.25233(18) 0.16961(17) 0.27786(14) 0.0306(4) Uani 1 1 d . . . . .
C2 C 0.10417(19) 0.11744(19) 0.33420(15) 0.0375(4) Uani 1 1 d . . . . .
H2 H 0.032796 0.170237 0.373078 0.045 Uiso 1 1 calc R U . . .
C3 C 0.0638(2) -0.0107(2) 0.33241(17) 0.0445(5) Uani 1 1 d . . . . .
H3 H -0.036265 -0.046022 0.370074 0.053 Uiso 1 1 calc R U . . .
C4 C 0.1678(2) -0.0896(2) 0.27599(18) 0.0454(5) Uani 1 1 d . . . . .
H4 H 0.137320 -0.178248 0.276645 0.054 Uiso 1 1 calc R U . . .
C5 C 0.3137(2) -0.04176(19) 0.21933(17) 0.0412(4) Uani 1 1 d . . . . .
H5 H 0.384067 -0.095653 0.180864 0.049 Uiso 1 1 calc R U . . .
C6 C 0.35435(19) 0.08871(17) 0.22056(14) 0.0331(4) Uani 1 1 d . . . . .
C7 C 0.48321(17) 0.28483(17) 0.19324(13) 0.0291(3) Uani 1 1 d . . . . .
C8 C 0.33555(17) 0.29479(17) 0.26279(13) 0.0286(3) Uani 1 1 d . . . . .
C9 C 0.30353(17) 0.41066(17) 0.30315(13) 0.0290(4) Uani 1 1 d . . . . .
C10 C 0.41289(17) 0.51367(17) 0.27279(13) 0.0304(4) Uani 1 1 d . . . . .
H10 H 0.390819 0.591216 0.301826 0.036 Uiso 1 1 calc R U . . .
C11 C 0.55595(17) 0.50597(17) 0.19991(13) 0.0294(4) Uani 1 1 d . . . . .
C12 C 0.59415(17) 0.39130(17) 0.15859(13) 0.0293(3) Uani 1 1 d . . . . .
C13 C 0.74856(18) 0.38318(18) 0.08318(15) 0.0342(4) Uani 1 1 d . . . . .
C14 C 0.8751(2) 0.3568(2) 0.13757(18) 0.0471(5) Uani 1 1 d . . . . .
H14A H 0.879299 0.427367 0.176315 0.071 Uiso 1 1 calc R U . . .
H14B H 0.969787 0.360141 0.078645 0.071 Uiso 1 1 calc R U . . .
H14C H 0.862067 0.265123 0.194605 0.071 Uiso 1 1 calc R U . . .
C15 C 0.7646(2) 0.4040(2) -0.03272(17) 0.0475(5) Uani 1 1 d . . . . .
H15A H 0.866(3) 0.398(3) -0.078(2) 0.056(6) Uiso 1 1 d . . . . .
H15B H 0.679(4) 0.424(3) -0.066(3) 0.079(9) Uiso 1 1 d . . . . .
C16 C 0.66670(17) 0.62293(17) 0.17047(14) 0.0311(4) Uani 1 1 d . . . . .
C17 C 0.7187(2) 0.6508(2) 0.25769(16) 0.0393(4) Uani 1 1 d . . . . .
H17 H 0.680979 0.597562 0.335832 0.047 Uiso 1 1 calc R U . . .
C18 C 0.8258(2) 0.7561(2) 0.23153(18) 0.0452(5) Uani 1 1 d . . . . .
H18 H 0.861372 0.773760 0.291686 0.054 Uiso 1 1 calc R U . . .
C19 C 0.8803(2) 0.83476(19) 0.11830(17) 0.0418(4) Uani 1 1 d . . . . .
H19 H 0.954867 0.905218 0.100329 0.050 Uiso 1 1 calc R U . . .
C20 C 0.8261(2) 0.81084(18) 0.03126(16) 0.0392(4) Uani 1 1 d . . . . .
H20 H 0.861582 0.866466 -0.046412 0.047 Uiso 1 1 calc R U . . .
C21 C 0.71972(19) 0.70533(18) 0.05720(15) 0.0353(4) Uani 1 1 d . . . . .
H21 H 0.682895 0.689411 -0.003080 0.042 Uiso 1 1 calc R U . . .
C22 C 0.6248(2) 0.0920(2) 0.1179(2) 0.0550(6) Uani 1 1 d . . . . .
H22A H 0.611360 -0.008728 0.149309 0.082 Uiso 1 1 calc R U . . .
H22B H 0.715416 0.120723 0.135301 0.082 Uiso 1 1 calc R U . . .
H22C H 0.636715 0.119056 0.033946 0.082 Uiso 1 1 calc R U . . .
C23 C 0.15299(18) 0.42524(18) 0.38097(15) 0.0349(4) Uani 1 1 d . . . . .
C24 C 0.3560(3) 0.7120(3) 0.5170(2) 0.0657(7) Uani 1 1 d . . . . .
H24A H 0.376007 0.723875 0.433775 0.098 Uiso 0.686(6) 1 calc R U P A 1
H24B H 0.258762 0.662699 0.556024 0.098 Uiso 0.686(6) 1 calc R U P A 1
H24C H 0.437432 0.658412 0.547926 0.098 Uiso 0.686(6) 1 calc R U P A 1
H24D H 0.389903 0.633511 0.486857 0.098 Uiso 0.314(6) 1 calc R U P A 2
H24E H 0.267559 0.753383 0.488505 0.098 Uiso 0.314(6) 1 calc R U P A 2
H24F H 0.328186 0.679747 0.601780 0.098 Uiso 0.314(6) 1 calc R U P A 2
C25 C 0.3493(4) 0.8532(3) 0.5378(3) 0.0517(9) Uani 0.686(6) 1 d . . P A 1
H25A H 0.271216 0.907782 0.501255 0.062 Uiso 0.686(6) 1 calc R U P A 1
H25B H 0.314564 0.839527 0.622119 0.062 Uiso 0.686(6) 1 calc R U P A 1
C26 C 0.4872(4) 0.9338(3) 0.4962(2) 0.0773(9) Uani 1 1 d . . . . .
H26C H 0.475505 0.890113 0.580263 0.093 Uiso 0.314(6) 1 calc R U P A 2
H26D H 0.381326 0.954620 0.489776 0.093 Uiso 0.314(6) 1 calc R U P A 2
H26A H 0.562388 0.873931 0.532414 0.093 Uiso 0.686(6) 1 calc R U P A 1
H26B H 0.519307 0.941747 0.412701 0.093 Uiso 0.686(6) 1 calc R U P A 1
C27 C 0.4840(9) 0.8199(7) 0.4765(6) 0.053(2) Uani 0.314(6) 1 d . . P A 2
H27A H 0.571333 0.769020 0.502466 0.064 Uiso 0.314(6) 1 calc R U P A 2
H27B H 0.510890 0.842241 0.391076 0.064 Uiso 0.314(6) 1 calc R U 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 C23 1.340(2) . ?
F2 C23 1.329(2) . ?
F3 C23 1.340(2) . ?
N1 C6 1.386(2) . ?
N1 C7 1.386(2) . ?
N1 C22 1.451(2) . ?
C1 C2 1.407(2) . ?
C1 C6 1.407(2) . ?
C1 C8 1.452(2) . ?
C2 H2 0.9500 . ?
C2 C3 1.375(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.397(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.380(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.396(3) . ?
C7 C8 1.425(2) . ?
C7 C12 1.412(2) . ?
C8 C9 1.397(2) . ?
C9 C10 1.384(2) . ?
C9 C23 1.499(2) . ?
C10 H10 0.9500 . ?
C10 C11 1.405(2) . ?
C11 C12 1.398(2) . ?
C11 C16 1.497(2) . ?
C12 C13 1.499(2) . ?
C13 C14 1.446(2) . ?
C13 C15 1.368(3) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.96(3) . ?
C15 H15B 0.95(3) . ?
C16 C17 1.390(2) . ?
C16 C21 1.391(2) . ?
C17 H17 0.9500 . ?
C17 C18 1.394(2) . ?
C18 H18 0.9500 . ?
C18 C19 1.381(3) . ?
C19 H19 0.9500 . ?
C19 C20 1.380(3) . ?
C20 H20 0.9500 . ?
C20 C21 1.392(2) . ?
C21 H21 0.9500 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C24 H24D 0.9800 . ?
C24 H24E 0.9800 . ?
C24 H24F 0.9800 . ?
C24 C25 1.522(4) . ?
C24 C27 1.526(8) . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
C25 C26 1.431(4) . ?
C26 C26 1.406(5) 2_676 ?
C26 H26C 0.9900 . ?
C26 H26D 0.9900 . ?
C26 H26A 0.9900 . ?
C26 H26B 0.9900 . ?
C26 C27 1.252(7) . ?
C27 H27A 0.9900 . ?
C27 H27B 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 C22 121.42(16) . . ?
C7 N1 C6 108.92(13) . . ?
C7 N1 C22 129.11(15) . . ?
C2 C1 C8 135.23(16) . . ?
C6 C1 C2 118.61(16) . . ?
C6 C1 C8 106.16(14) . . ?
C1 C2 H2 120.3 . . ?
C3 C2 C1 119.34(18) . . ?
C3 C2 H2 120.3 . . ?
C2 C3 H3 119.5 . . ?
C2 C3 C4 120.92(18) . . ?
C4 C3 H3 119.5 . . ?
C3 C4 H4 119.3 . . ?
C5 C4 C3 121.43(18) . . ?
C5 C4 H4 119.3 . . ?
C4 C5 H5 121.2 . . ?
C4 C5 C6 117.61(19) . . ?
C6 C5 H5 121.2 . . ?
N1 C6 C1 109.69(15) . . ?
N1 C6 C5 128.23(17) . . ?
C5 C6 C1 122.08(16) . . ?
N1 C7 C8 108.38(14) . . ?
N1 C7 C12 129.37(15) . . ?
C12 C7 C8 122.24(15) . . ?
C7 C8 C1 106.80(14) . . ?
C9 C8 C1 134.80(15) . . ?
C9 C8 C7 118.36(15) . . ?
C8 C9 C23 121.35(15) . . ?
C10 C9 C8 119.88(14) . . ?
C10 C9 C23 118.76(15) . . ?
C9 C10 H10 119.3 . . ?
C9 C10 C11 121.38(15) . . ?
C11 C10 H10 119.3 . . ?
C10 C11 C16 117.76(14) . . ?
C12 C11 C10 120.88(15) . . ?
C12 C11 C16 121.35(14) . . ?
C7 C12 C13 122.63(15) . . ?
C11 C12 C7 117.15(14) . . ?
C11 C12 C13 120.20(14) . . ?
C14 C13 C12 117.40(15) . . ?
C15 C13 C12 119.47(16) . . ?
C15 C13 C14 123.11(16) . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C13 C15 H15A 116.8(14) . . ?
C13 C15 H15B 120.7(18) . . ?
H15A C15 H15B 122(2) . . ?
C17 C16 C11 119.73(15) . . ?
C17 C16 C21 118.64(16) . . ?
C21 C16 C11 121.62(15) . . ?
C16 C17 H17 119.7 . . ?
C16 C17 C18 120.57(17) . . ?
C18 C17 H17 119.7 . . ?
C17 C18 H18 119.9 . . ?
C19 C18 C17 120.10(18) . . ?
C19 C18 H18 119.9 . . ?
C18 C19 H19 120.1 . . ?
C20 C19 C18 119.88(17) . . ?
C20 C19 H19 120.1 . . ?
C19 C20 H20 120.0 . . ?
C19 C20 C21 120.06(16) . . ?
C21 C20 H20 120.0 . . ?
C16 C21 H21 119.7 . . ?
C20 C21 C16 120.69(16) . . ?
C20 C21 H21 119.7 . . ?
N1 C22 H22A 109.5 . . ?
N1 C22 H22B 109.5 . . ?
N1 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
F1 C23 F3 105.95(14) . . ?
F1 C23 C9 112.29(14) . . ?
F2 C23 F1 106.62(14) . . ?
F2 C23 F3 106.30(14) . . ?
F2 C23 C9 112.76(14) . . ?
F3 C23 C9 112.43(14) . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
H24D C24 H24E 109.5 . . ?
H24D C24 H24F 109.5 . . ?
H24E C24 H24F 109.5 . . ?
C25 C24 H24A 109.5 . . ?
C25 C24 H24B 109.5 . . ?
C25 C24 H24C 109.5 . . ?
C27 C24 H24D 109.5 . . ?
C27 C24 H24E 109.5 . . ?
C27 C24 H24F 109.5 . . ?
C24 C25 H25A 108.1 . . ?
C24 C25 H25B 108.1 . . ?
H25A C25 H25B 107.3 . . ?
C26 C25 C24 116.8(3) . . ?
C26 C25 H25A 108.1 . . ?
C26 C25 H25B 108.1 . . ?
C25 C26 H26A 105.1 . . ?
C25 C26 H26B 105.1 . . ?
C26 C26 C25 128.6(4) 2_676 . ?
C26 C26 H26C 92.9 2_676 . ?
C26 C26 H26D 92.9 2_676 . ?
C26 C26 H26A 105.1 2_676 . ?
C26 C26 H26B 105.1 2_676 . ?
H26C C26 H26D 103.0 . . ?
H26A C26 H26B 105.9 . . ?
C27 C26 C26 170.5(6) . 2_676 ?
C27 C26 H26C 92.9 . . ?
C27 C26 H26D 92.9 . . ?
C24 C27 H27A 104.9 . . ?
C24 C27 H27B 104.9 . . ?
C26 C27 C24 129.6(6) . . ?
C26 C27 H27A 104.9 . . ?
C26 C27 H27B 104.9 . . ?
H27A C27 H27B 105.8 . . ?

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
N1 C7 C8 C1 -2.07(17) . . . . ?
N1 C7 C8 C9 175.86(13) . . . . ?
N1 C7 C12 C11 -176.64(15) . . . . ?
N1 C7 C12 C13 1.9(3) . . . . ?
C1 C2 C3 C4 0.3(3) . . . . ?
C1 C8 C9 C10 178.85(16) . . . . ?
C1 C8 C9 C23 -0.1(3) . . . . ?
C2 C1 C6 N1 179.48(14) . . . . ?
C2 C1 C6 C5 -0.9(2) . . . . ?
C2 C1 C8 C7 -178.81(18) . . . . ?
C2 C1 C8 C9 3.8(3) . . . . ?
C2 C3 C4 C5 -0.6(3) . . . . ?
C3 C4 C5 C6 0.2(3) . . . . ?
C4 C5 C6 N1 -179.87(16) . . . . ?
C4 C5 C6 C1 0.6(3) . . . . ?
C6 N1 C7 C8 1.41(18) . . . . ?
C6 N1 C7 C12 -179.00(15) . . . . ?
C6 C1 C2 C3 0.5(2) . . . . ?
C6 C1 C8 C7 1.94(16) . . . . ?
C6 C1 C8 C9 -175.50(17) . . . . ?
C7 N1 C6 C1 -0.15(18) . . . . ?
C7 N1 C6 C5 -179.76(16) . . . . ?
C7 C8 C9 C10 1.6(2) . . . . ?
C7 C8 C9 C23 -177.31(14) . . . . ?
C7 C12 C13 C14 -106.0(2) . . . . ?
C7 C12 C13 C15 75.6(2) . . . . ?
C8 C1 C2 C3 -178.73(17) . . . . ?
C8 C1 C6 N1 -1.12(17) . . . . ?
C8 C1 C6 C5 178.51(15) . . . . ?
C8 C7 C12 C11 2.9(2) . . . . ?
C8 C7 C12 C13 -178.56(14) . . . . ?
C8 C9 C10 C11 1.2(2) . . . . ?
C8 C9 C23 F1 58.3(2) . . . . ?
C8 C9 C23 F2 178.76(14) . . . . ?
C8 C9 C23 F3 -61.1(2) . . . . ?
C9 C10 C11 C12 -2.1(2) . . . . ?
C9 C10 C11 C16 179.29(14) . . . . ?
C10 C9 C23 F1 -120.66(16) . . . . ?
C10 C9 C23 F2 -0.2(2) . . . . ?
C10 C9 C23 F3 119.97(16) . . . . ?
C10 C11 C12 C7 0.0(2) . . . . ?
C10 C11 C12 C13 -178.56(14) . . . . ?
C10 C11 C16 C17 62.7(2) . . . . ?
C10 C11 C16 C21 -117.40(17) . . . . ?
C11 C12 C13 C14 72.5(2) . . . . ?
C11 C12 C13 C15 -105.9(2) . . . . ?
C11 C16 C17 C18 177.75(16) . . . . ?
C11 C16 C21 C20 -178.03(15) . . . . ?
C12 C7 C8 C1 178.31(13) . . . . ?
C12 C7 C8 C9 -3.8(2) . . . . ?
C12 C11 C16 C17 -115.96(18) . . . . ?
C12 C11 C16 C21 64.0(2) . . . . ?
C16 C11 C12 C7 178.60(13) . . . . ?
C16 C11 C12 C13 0.0(2) . . . . ?
C16 C17 C18 C19 0.6(3) . . . . ?
C17 C16 C21 C20 1.9(3) . . . . ?
C17 C18 C19 C20 1.3(3) . . . . ?
C18 C19 C20 C21 -1.6(3) . . . . ?
C19 C20 C21 C16 0.0(3) . . . . ?
C21 C16 C17 C18 -2.2(3) . . . . ?
C22 N1 C6 C1 172.07(17) . . . . ?
C22 N1 C6 C5 -7.5(3) . . . . ?
C22 N1 C7 C8 -170.04(18) . . . . ?
C22 N1 C7 C12 9.6(3) . . . . ?
C23 C9 C10 C11 -179.83(14) . . . . ?
C24 C25 C26 C26 -179.9(3) . . . 2_676 ?

_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 2.284
_oxdiff_exptl_absorpt_empirical_full_min 0.506
