# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2023

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

data_202110
_database_code_depnum_ccdc_archive 'CCDC 2159180'
loop_
_audit_author_name
_audit_author_address
'yakun wang'
;School of Pharmacy, Xinxiang Medical University
China
;
_audit_update_record             
;
2022-03-16 deposited with the CCDC.	2023-03-21 downloaded from the CCDC.
;
_audit_creation_date             2021-11-01
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C25 H20 F4 N2 O3'
_chemical_formula_sum            'C25 H20 F4 N2 O3'
_chemical_formula_weight         472.43
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         C30H3N1O4
_chemical_oxdiff_usercomment     r
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   8.5752(4)
_cell_length_b                   12.4172(6)
_cell_length_c                   20.9749(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2233.40(17)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6539
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.2690
_cell_measurement_theta_min      4.1210
_shelx_estimated_absorpt_T_max   0.908
_shelx_estimated_absorpt_T_min   0.858
_exptl_absorpt_coefficient_mu    0.987
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.82084
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.405
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             976
_exptl_crystal_size_max          0.16
_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  0.0412
_diffrn_reflns_av_unetI/netI     0.0294
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            22488
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.354
_diffrn_reflns_theta_min         4.137
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2312
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -101.00 -10.00   1.00    1.10    --  -33.50 -67.00 -43.00   91
  2  ω    -56.00 -20.00   1.00    1.10    --  -33.50  67.00  90.00   36
  3  ω     -3.00  34.00   1.00    1.10    --  -33.50  67.00  90.00   37
  4  ω     38.00  64.00   1.00    1.10    --   36.47-126.00  78.00   26
  5  ω     26.00  52.00   1.00    1.10    --   36.47  37.00-180.00   26
  6  ω     62.00  95.00   1.00    1.10    --   36.47 178.00  30.00   33
  7  ω     69.00  95.00   1.00    1.10    --   36.47  77.00-120.00   26
  8  ω     80.00 105.00   1.00    1.10    --   36.47  57.00-150.00   25
  9  ω     -1.00 103.00   1.00    1.10    --   36.47   0.00 -60.00  104
 10  ω     -3.00  35.00   1.00    1.10    --   36.47 -99.00  60.00   38
 11  ω     61.00 105.00   1.00    1.10    --   36.47  37.00-180.00   44
 12  ω     59.00 107.00   1.00    1.10    --   36.47 178.00-150.00   48
 13  ω     -2.00  23.00   1.00    1.10    --   36.47 -99.00 -90.00   25
 14  ω      6.00  73.00   1.00    1.10    --   36.47 -99.00-150.00   67
 15  ω     50.00  76.00   1.00    1.10    --   36.47 -99.00 -90.00   26
 16  ω      8.00  34.00   1.00    1.10    --   36.47  77.00-120.00   26
 17  ω     58.00  92.00   1.00    1.10    --   36.47 178.00  60.00   34
 18  ω    -34.00  -6.00   1.00    1.10    --   36.47   0.00 -60.00   28
 19  ω     67.00  92.00   1.00    1.10    --   36.47-126.00  78.00   25
 20  ω    135.00 161.00   1.00    8.00    --  108.00  45.00  60.00   26
 21  ω     97.00 123.00   1.00    8.00    --  108.00  45.00  60.00   26
 22  ω     40.00  66.00   1.00    8.00    --  108.00 -67.00 -43.00   26
 23  ω    128.00 172.00   1.00    8.00    --  108.00  77.00 150.00   44
 24  ω     89.00 160.00   1.00    8.00    --  108.00  45.00-120.00   71
 25  ω    128.00 167.00   1.00    8.00    --  108.00  61.00-150.00   39
 26  ω     94.00 120.00   1.00    8.00    --  108.00  61.00-120.00   26
 27  ω     88.00 114.00   1.00    8.00    --  108.00  45.00-180.00   26
 28  ω     39.00 110.00   1.00    8.00    --  108.00 -94.00-180.00   71
 29  ω     88.00 122.00   1.00    8.00    --  108.00  61.00-150.00   34
 30  ω     50.00 120.00   1.00    8.00    --  108.00 -45.00 150.00   70
 31  ω    151.00 176.00   1.00    8.00    --  108.00  67.00  90.00   25
 32  ω     73.00 130.00   1.00    8.00    --  108.00  15.00  30.00   57
 33  ω     90.00 116.00   1.00    8.00    --  108.00  30.00 150.00   26
 34  ω     54.00  80.00   1.00    8.00    --  108.00 -94.00 -90.00   26
 35  ω     46.00 111.00   1.00    8.00    --  108.00-111.00  30.00   65
 36  ω    124.00 175.00   1.00    8.00    --  108.00  77.00-180.00   51
 37  ω     85.00 131.00   1.00    8.00    --  108.00  67.00  90.00   46
 38  ω    121.00 152.00   1.00    8.00    --  108.00 -15.00 150.00   31
 39  ω     83.00 109.00   1.00    8.00    --  108.00  77.00-180.00   26
 40  ω     40.00  66.00   1.00    8.00    --  108.00 -15.00 150.00   26
 41  ω     89.00 114.00   1.00    8.00    --  108.00  61.00-180.00   25
 42  ω     83.00 112.00   1.00    8.00    --  108.00 -61.00-180.00   29
 43  ω     83.00 108.00   1.00    8.00    --  108.00  30.00-120.00   25
 44  ω    106.00 170.00   1.00    8.00    --  108.00  77.00  60.00   64
 45  ω    131.00 176.00   1.00    8.00    --  108.00  61.00 120.00   45
 46  ω    143.00 168.00   1.00    8.00    --  108.00  30.00 150.00   25
 47  ω     42.00  67.00   1.00    8.00    --  108.00 -77.00  30.00   25
 48  ω     79.00 137.00   1.00    8.00    --  108.00 -77.00  30.00   58
 49  ω     93.00 127.00   1.00    8.00    --  108.00  61.00   0.00   34
 50  ω     84.00 110.00   1.00    8.00    --  108.00  30.00-150.00   26
 51  ω     88.00 114.00   1.00    8.00    --  108.00  61.00 120.00   26
 52  ω     43.00  69.00   1.00    8.00    --  108.00 -94.00  90.00   26
 53  ω     88.00 131.00   1.00    8.00    --  108.00 -67.00 -43.00   43
 54  ω    136.00 169.00   1.00    8.00    --  108.00  15.00  30.00   33
 55  ω    132.00 159.00   1.00    8.00    --  108.00  37.00 178.99   27
 56  ω     88.00 114.00   1.00    8.00    --  108.00  45.00-150.00   26
 57  ω     84.00 109.00   1.00    8.00    --  108.00  30.00-180.00   25
 58  ω     89.00 122.00   1.00    8.00    --  108.00  37.00 178.99   33
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1256567000
_diffrn_orient_matrix_UB_12      -0.0688933000
_diffrn_orient_matrix_UB_13      -0.0330666000
_diffrn_orient_matrix_UB_21      0.0545862000
_diffrn_orient_matrix_UB_22      -0.0419941000
_diffrn_orient_matrix_UB_23      0.0654109000
_diffrn_orient_matrix_UB_31      -0.1161789000
_diffrn_orient_matrix_UB_32      -0.0942323000
_diffrn_orient_matrix_UB_33      -0.0049695000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.744
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.986
_reflns_number_gt                3792
_reflns_number_total             4307
_reflns_odcompleteness_completeness 99.92
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     69.95
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.215
_refine_diff_density_min         -0.200
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details 
;
 Flack x determined using 1464 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.01(9)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     309
_refine_ls_number_reflns         4307
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0493
_refine_ls_R_factor_gt           0.0425
_refine_ls_restrained_S_all      1.052
_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)+(0.0640P)²+0.1872P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1094
_refine_ls_wR_factor_ref         0.1179
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B)
2.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C8(H8), C9(H9), C13(H13), C15(H15), C17(H17), C21(H21),
 C22(H22), C23(H23), C24(H24), C25(H25)
2.c Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C19(H19A,H19B,H19C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.4402(2) 0.97242(13) 0.25771(10) 0.0649(5) Uani 1 1 d . . . . .
F2 F 1.0689(4) 0.8349(3) 0.4638(2) 0.1303(14) Uani 1 1 d . . . . .
F3 F 1.0673(3) 0.6646(2) 0.45671(12) 0.0922(8) Uani 1 1 d . . . . .
F4 F 0.9093(3) 0.7447(3) 0.51710(11) 0.1132(12) Uani 1 1 d . . . . .
O1 O 0.2518(3) 0.8933(2) 0.15177(13) 0.0734(7) Uani 1 1 d . . . . .
O2 O 0.0064(3) 0.5292(3) 0.18975(17) 0.0875(9) Uani 1 1 d . . . . .
O3 O 0.3159(4) 0.45748(19) 0.36735(13) 0.0735(7) Uani 1 1 d . . . . .
N1 N 0.4461(3) 0.76320(19) 0.15838(12) 0.0517(5) Uani 1 1 d . . . . .
N2 N 0.5610(3) 0.73450(18) 0.20284(11) 0.0492(5) Uani 1 1 d . . . . .
C1 C 0.3538(4) 0.8461(2) 0.17979(16) 0.0557(7) Uani 1 1 d . . . . .
C2 C 0.4039(3) 0.8642(2) 0.24916(15) 0.0507(6) Uani 1 1 d . . . . .
C3 C 0.5451(3) 0.7915(2) 0.25323(13) 0.0463(5) Uani 1 1 d . . . . .
C4 C 0.6509(3) 0.7796(2) 0.30786(13) 0.0471(6) Uani 1 1 d . . . . .
C5 C 0.6667(4) 0.8614(3) 0.35292(16) 0.0578(7) Uani 1 1 d . . . . .
H5 H 0.6062 0.9233 0.3497 0.069 Uiso 1 1 calc R . . . .
C6 C 0.7712(4) 0.8509(3) 0.40196(16) 0.0607(7) Uani 1 1 d . . . . .
H6 H 0.7821 0.9060 0.4316 0.073 Uiso 1 1 calc R . . . .
C7 C 0.8603(3) 0.7587(3) 0.40754(13) 0.0524(6) Uani 1 1 d . . . . .
C8 C 0.8430(4) 0.6762(3) 0.36410(15) 0.0581(7) Uani 1 1 d . . . . .
H8 H 0.9015 0.6136 0.3684 0.070 Uiso 1 1 calc R . . . .
C9 C 0.7387(4) 0.6866(2) 0.31427(15) 0.0560(7) Uani 1 1 d . . . . .
H9 H 0.7275 0.6310 0.2849 0.067 Uiso 1 1 calc R . . . .
C10 C 0.9752(4) 0.7501(3) 0.46051(16) 0.0648(8) Uani 1 1 d . . . . .
C11 C 0.2728(4) 0.8342(2) 0.29491(16) 0.0559(7) Uani 1 1 d . . . . .
H11A H 0.3052 0.8502 0.3382 0.067 Uiso 1 1 calc R . . . .
H11B H 0.1818 0.8777 0.2855 0.067 Uiso 1 1 calc R . . . .
C12 C 0.2293(3) 0.7162(2) 0.29037(15) 0.0539(6) Uani 1 1 d . . . . .
C13 C 0.1316(3) 0.6811(3) 0.24168(17) 0.0608(7) Uani 1 1 d . . . . .
H13 H 0.0882 0.7300 0.2131 0.073 Uiso 1 1 calc R . . . .
C14 C 0.0997(4) 0.5717(3) 0.23640(19) 0.0650(8) Uani 1 1 d . . . . .
C15 C 0.1597(4) 0.4992(3) 0.27970(18) 0.0644(8) Uani 1 1 d . . . . .
H15 H 0.1344 0.4265 0.2767 0.077 Uiso 1 1 calc R . . . .
C16 C 0.2572(4) 0.5349(2) 0.32752(16) 0.0577(7) Uani 1 1 d . . . . .
C17 C 0.2924(4) 0.6440(3) 0.33331(14) 0.0531(6) Uani 1 1 d . . . . .
H17 H 0.3578 0.6679 0.3657 0.064 Uiso 1 1 calc R . . . .
C18 C -0.0389(7) 0.5970(5) 0.1391(3) 0.1061(16) Uani 1 1 d . . . . .
H18A H -0.1079 0.6517 0.1548 0.159 Uiso 1 1 calc GR . . . .
H18B H -0.0915 0.5552 0.1071 0.159 Uiso 1 1 calc GR . . . .
H18C H 0.0518 0.6301 0.1208 0.159 Uiso 1 1 calc GR . . . .
C19 C 0.4056(5) 0.4923(3) 0.4193(2) 0.0787(10) Uani 1 1 d . . . . .
H19A H 0.4374 0.4312 0.4441 0.118 Uiso 1 1 calc GR . . . .
H19B H 0.3447 0.5400 0.4453 0.118 Uiso 1 1 calc GR . . . .
H19C H 0.4962 0.5296 0.4040 0.118 Uiso 1 1 calc GR . . . .
C20 C 0.4461(4) 0.7103(2) 0.09845(15) 0.0548(6) Uani 1 1 d . . . . .
C21 C 0.3535(5) 0.7468(3) 0.04877(18) 0.0720(9) Uani 1 1 d . . . . .
H21 H 0.2874 0.8053 0.0544 0.086 Uiso 1 1 calc R . . . .
C22 C 0.3616(6) 0.6940(4) -0.00966(19) 0.0841(12) Uani 1 1 d . . . . .
H22 H 0.3004 0.7184 -0.0433 0.101 Uiso 1 1 calc R . . . .
C23 C 0.4570(6) 0.6073(4) -0.0189(2) 0.0865(12) Uani 1 1 d . . . . .
H23 H 0.4622 0.5738 -0.0585 0.104 Uiso 1 1 calc R . . . .
C24 C 0.5455(6) 0.5699(4) 0.0314(2) 0.0824(11) Uani 1 1 d . . . . .
H24 H 0.6091 0.5100 0.0259 0.099 Uiso 1 1 calc R . . . .
C25 C 0.5406(4) 0.6209(3) 0.08993(17) 0.0647(8) Uani 1 1 d . . . . .
H25 H 0.6007 0.5952 0.1236 0.078 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C2 1.391(3) . ?
F2 C10 1.327(5) . ?
F3 C10 1.325(4) . ?
F4 C10 1.316(4) . ?
O1 C1 1.206(4) . ?
O2 C14 1.370(5) . ?
O2 C18 1.410(7) . ?
O3 C16 1.369(4) . ?
O3 C19 1.402(5) . ?
N1 N2 1.403(3) . ?
N1 C1 1.373(4) . ?
N1 C20 1.419(4) . ?
N2 C3 1.279(4) . ?
C1 C2 1.534(4) . ?
C2 C3 1.513(4) . ?
C2 C11 1.524(4) . ?
C3 C4 1.469(4) . ?
C4 C5 1.394(4) . ?
C4 C9 1.385(4) . ?
C5 H5 0.9300 . ?
C5 C6 1.370(5) . ?
C6 H6 0.9300 . ?
C6 C7 1.381(5) . ?
C7 C8 1.379(4) . ?
C7 C10 1.489(4) . ?
C8 H8 0.9300 . ?
C8 C9 1.381(4) . ?
C9 H9 0.9300 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 C12 1.514(4) . ?
C12 C13 1.392(5) . ?
C12 C17 1.382(5) . ?
C13 H13 0.9300 . ?
C13 C14 1.389(5) . ?
C14 C15 1.378(6) . ?
C15 H15 0.9300 . ?
C15 C16 1.379(5) . ?
C16 C17 1.393(4) . ?
C17 H17 0.9300 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 C21 1.386(5) . ?
C20 C25 1.386(5) . ?
C21 H21 0.9300 . ?
C21 C22 1.391(6) . ?
C22 H22 0.9300 . ?
C22 C23 1.367(7) . ?
C23 H23 0.9300 . ?
C23 C24 1.380(7) . ?
C24 H24 0.9300 . ?
C24 C25 1.381(5) . ?
C25 H25 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C14 O2 C18 118.0(4) . . ?
C16 O3 C19 117.4(3) . . ?
N2 N1 C20 118.1(2) . . ?
C1 N1 N2 112.2(2) . . ?
C1 N1 C20 129.6(3) . . ?
C3 N2 N1 109.5(2) . . ?
O1 C1 N1 128.5(3) . . ?
O1 C1 C2 126.4(3) . . ?
N1 C1 C2 105.0(2) . . ?
F1 C2 C1 109.1(2) . . ?
F1 C2 C3 112.9(2) . . ?
F1 C2 C11 108.7(2) . . ?
C3 C2 C1 100.9(2) . . ?
C3 C2 C11 114.1(2) . . ?
C11 C2 C1 110.8(3) . . ?
N2 C3 C2 111.6(2) . . ?
N2 C3 C4 121.5(2) . . ?
C4 C3 C2 126.8(2) . . ?
C5 C4 C3 121.0(3) . . ?
C9 C4 C3 119.7(3) . . ?
C9 C4 C5 119.2(3) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 C4 120.2(3) . . ?
C6 C5 H5 119.9 . . ?
C5 C6 H6 119.9 . . ?
C5 C6 C7 120.3(3) . . ?
C7 C6 H6 119.9 . . ?
C6 C7 C10 119.2(3) . . ?
C8 C7 C6 120.0(3) . . ?
C8 C7 C10 120.7(3) . . ?
C7 C8 H8 120.0 . . ?
C7 C8 C9 120.0(3) . . ?
C9 C8 H8 120.0 . . ?
C4 C9 H9 119.9 . . ?
C8 C9 C4 120.2(3) . . ?
C8 C9 H9 119.9 . . ?
F2 C10 C7 112.5(3) . . ?
F3 C10 F2 106.2(3) . . ?
F3 C10 C7 114.0(3) . . ?
F4 C10 F2 104.7(4) . . ?
F4 C10 F3 105.6(3) . . ?
F4 C10 C7 113.1(3) . . ?
C2 C11 H11A 109.2 . . ?
C2 C11 H11B 109.2 . . ?
H11A C11 H11B 107.9 . . ?
C12 C11 C2 112.3(2) . . ?
C12 C11 H11A 109.2 . . ?
C12 C11 H11B 109.2 . . ?
C13 C12 C11 119.9(3) . . ?
C17 C12 C11 119.4(3) . . ?
C17 C12 C13 120.7(3) . . ?
C12 C13 H13 120.5 . . ?
C14 C13 C12 118.9(3) . . ?
C14 C13 H13 120.5 . . ?
O2 C14 C13 123.3(4) . . ?
O2 C14 C15 115.9(3) . . ?
C15 C14 C13 120.9(3) . . ?
C14 C15 H15 120.1 . . ?
C14 C15 C16 119.7(3) . . ?
C16 C15 H15 120.1 . . ?
O3 C16 C15 116.2(3) . . ?
O3 C16 C17 123.3(3) . . ?
C15 C16 C17 120.5(3) . . ?
C12 C17 C16 119.3(3) . . ?
C12 C17 H17 120.3 . . ?
C16 C17 H17 120.3 . . ?
O2 C18 H18A 109.5 . . ?
O2 C18 H18B 109.5 . . ?
O2 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
O3 C19 H19A 109.5 . . ?
O3 C19 H19B 109.5 . . ?
O3 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C21 C20 N1 121.0(3) . . ?
C21 C20 C25 120.0(3) . . ?
C25 C20 N1 119.0(3) . . ?
C20 C21 H21 120.7 . . ?
C20 C21 C22 118.7(4) . . ?
C22 C21 H21 120.7 . . ?
C21 C22 H22 119.1 . . ?
C23 C22 C21 121.7(4) . . ?
C23 C22 H22 119.1 . . ?
C22 C23 H23 120.5 . . ?
C22 C23 C24 119.1(4) . . ?
C24 C23 H23 120.5 . . ?
C23 C24 H24 119.7 . . ?
C23 C24 C25 120.6(4) . . ?
C25 C24 H24 119.7 . . ?
C20 C25 H25 120.0 . . ?
C24 C25 C20 119.9(4) . . ?
C24 C25 H25 120.0 . . ?

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 C2 C3 N2 -123.6(3) . . . . ?
F1 C2 C3 C4 59.5(4) . . . . ?
F1 C2 C11 C12 -178.1(3) . . . . ?
O1 C1 C2 F1 -54.8(4) . . . . ?
O1 C1 C2 C3 -173.9(3) . . . . ?
O1 C1 C2 C11 64.8(4) . . . . ?
O2 C14 C15 C16 178.8(3) . . . . ?
O3 C16 C17 C12 179.2(3) . . . . ?
N1 N2 C3 C2 3.5(3) . . . . ?
N1 N2 C3 C4 -179.3(2) . . . . ?
N1 C1 C2 F1 127.2(3) . . . . ?
N1 C1 C2 C3 8.1(3) . . . . ?
N1 C1 C2 C11 -113.2(3) . . . . ?
N1 C20 C21 C22 178.0(4) . . . . ?
N1 C20 C25 C24 -178.2(3) . . . . ?
N2 N1 C1 O1 175.1(3) . . . . ?
N2 N1 C1 C2 -6.9(3) . . . . ?
N2 N1 C20 C21 -169.1(3) . . . . ?
N2 N1 C20 C25 10.8(4) . . . . ?
N2 C3 C4 C5 159.3(3) . . . . ?
N2 C3 C4 C9 -19.5(4) . . . . ?
C1 N1 N2 C3 2.4(3) . . . . ?
C1 N1 C20 C21 6.4(5) . . . . ?
C1 N1 C20 C25 -173.6(3) . . . . ?
C1 C2 C3 N2 -7.3(3) . . . . ?
C1 C2 C3 C4 175.8(2) . . . . ?
C1 C2 C11 C12 62.1(3) . . . . ?
C2 C3 C4 C5 -24.0(4) . . . . ?
C2 C3 C4 C9 157.2(3) . . . . ?
C2 C11 C12 C13 -80.7(3) . . . . ?
C2 C11 C12 C17 96.7(3) . . . . ?
C3 C2 C11 C12 -51.0(4) . . . . ?
C3 C4 C5 C6 -177.0(3) . . . . ?
C3 C4 C9 C8 177.5(3) . . . . ?
C4 C5 C6 C7 -0.7(5) . . . . ?
C5 C4 C9 C8 -1.3(5) . . . . ?
C5 C6 C7 C8 -0.8(5) . . . . ?
C5 C6 C7 C10 178.8(3) . . . . ?
C6 C7 C8 C9 1.3(5) . . . . ?
C6 C7 C10 F2 -51.1(5) . . . . ?
C6 C7 C10 F3 -172.1(3) . . . . ?
C6 C7 C10 F4 67.2(5) . . . . ?
C7 C8 C9 C4 -0.2(5) . . . . ?
C8 C7 C10 F2 128.5(4) . . . . ?
C8 C7 C10 F3 7.5(5) . . . . ?
C8 C7 C10 F4 -113.2(4) . . . . ?
C9 C4 C5 C6 1.8(5) . . . . ?
C10 C7 C8 C9 -178.3(3) . . . . ?
C11 C2 C3 N2 111.6(3) . . . . ?
C11 C2 C3 C4 -65.4(4) . . . . ?
C11 C12 C13 C14 176.6(3) . . . . ?
C11 C12 C17 C16 -177.5(3) . . . . ?
C12 C13 C14 O2 -179.3(3) . . . . ?
C12 C13 C14 C15 2.0(5) . . . . ?
C13 C12 C17 C16 0.0(4) . . . . ?
C13 C14 C15 C16 -2.4(5) . . . . ?
C14 C15 C16 O3 -178.0(3) . . . . ?
C14 C15 C16 C17 1.6(5) . . . . ?
C15 C16 C17 C12 -0.4(5) . . . . ?
C17 C12 C13 C14 -0.8(4) . . . . ?
C18 O2 C14 C13 10.4(6) . . . . ?
C18 O2 C14 C15 -170.8(4) . . . . ?
C19 O3 C16 C15 -175.2(3) . . . . ?
C19 O3 C16 C17 5.2(5) . . . . ?
C20 N1 N2 C3 178.7(2) . . . . ?
C20 N1 C1 O1 -0.6(6) . . . . ?
C20 N1 C1 C2 177.3(3) . . . . ?
C20 C21 C22 C23 0.5(7) . . . . ?
C21 C20 C25 C24 1.7(6) . . . . ?
C21 C22 C23 C24 1.2(7) . . . . ?
C22 C23 C24 C25 -1.4(7) . . . . ?
C23 C24 C25 C20 0.0(7) . . . . ?
C25 C20 C21 C22 -1.9(6) . . . . ?

_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 1.303
_oxdiff_exptl_absorpt_empirical_full_min 0.908
