# Supplementary Information (SI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2026

####################################################################### 
# 
# 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_dkb-01-247
_database_code_depnum_ccdc_archive 'CCDC 2451792'
loop_
_audit_author_name
_audit_author_address
'Farzaneh Fadaei Tirani'
;EPFL
Switzerland
;
_audit_update_record             
;
2025-05-16 deposited with the CCDC.	2026-01-07 downloaded from the CCDC.
;
_audit_creation_date             2025-05-05
_audit_creation_method           
;
Olex2 1.5
(compiled 2025.04.05 svn.rf049d14d for OlexSys, GUI svn.r7224)
;
_shelx_SHELXL_version_number     2019/3
_audit_contact_author            'Farzaneh Fadaei Tirani'
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C27 H23 F3 N2 O5'
_chemical_formula_sum            'C27 H23 F3 N2 O5'
_chemical_formula_weight         512.47
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C27 H23 F3 N2 O5'
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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   25.4150(5)
_cell_length_b                   9.44890(15)
_cell_length_c                   21.1616(3)
_cell_angle_alpha                90
_cell_angle_beta                 110.432(2)
_cell_angle_gamma                90
_cell_volume                     4762.11(15)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    13170
_cell_measurement_temperature    140.00(10)
_cell_measurement_theta_max      75.3340
_cell_measurement_theta_min      3.6900
_shelx_estimated_absorpt_T_max   0.953
_shelx_estimated_absorpt_T_min   0.884
_exptl_absorpt_coefficient_mu    0.975
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.904
_exptl_absorpt_correction_type   Gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.94a (Rigaku Oxford Diffraction, 2024)
Numerical absorption correction based on Gaussian integration over
a multifaceted crystal model.
Empirical absorption correction using spherical harmonics
as implemented in SCALE3 ABSPACK scaling algorithm
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.430
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             2128
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 -1 0 0.0304
0 1 0 0.0227
0 0 1 0.0581
0 0 -1 0.0791
1 0 0 0.0430
-1 0 0 0.0497
-1 0 1 0.0455
1 0 -1 0.0581

_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.05
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-0.0000 -1.0000 0.0000 -0.0459 0.1437 0.0619
0.0000 1.0000 -0.0000 0.0459 -0.1437 -0.0619
0.0000 0.0000 1.0000 0.0229 -0.0231 0.0705
-0.0000 -0.0000 -1.0000 -0.0229 0.0231 -0.0705
1.0000 0.0000 -0.0000 -0.0487 -0.0290 0.0312
-1.0000 -0.0000 0.0000 0.0487 0.0290 -0.0312
-1.0000 0.0000 1.0000 0.0716 0.0060 0.0393
1.0000 -0.0000 -1.0000 -0.0716 -0.0060 -0.0393

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0349
_diffrn_reflns_av_unetI/netI     0.0270
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            23714
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.535
_diffrn_reflns_theta_min         3.712
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      140.00(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 1.000
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     61.00 114.00   0.50    0.20    --   79.75  21.00 117.83  106
  2  ω    101.00 127.00   0.50    0.20    --   79.75  22.00 153.37   52
  3  ω     69.00 119.00   0.50    0.20    --   79.75  22.00  30.52  100
  4  ω     84.00 113.00   0.50    0.20    --   79.75   5.00  78.77   58
  5  ω     61.00 126.00   0.50    0.20    --   79.75  17.00   1.27  130
  6  ω     49.00 111.00   0.50    0.20    --   79.75   4.00 167.58  124
  7  ω     49.00  82.00   0.50    0.20    --   79.75  15.00 -18.19   66
  8  ω     51.00 119.00   0.50    0.20    --   76.50  15.00 -90.00  136
  9  ω     62.00 110.00   0.50    0.20    --   79.75  21.00-170.05   96
 10  ω     36.00  61.00   0.50    0.20    --   79.75 -52.00-118.69   50
 11  ω     44.00  70.00   0.50    0.20    --   76.50-125.00 -90.00   52
 12  ω     68.00  93.00   0.50    0.20    --   76.50-125.00-120.00   50
 13  ω     76.00 101.00   0.50    0.20    --   76.50-125.00 -90.00   50
 14  ω     78.00 103.00   0.50    0.20    --   76.50-125.00 -30.00   50
 15  ω     78.00 103.00   0.50    0.20    --   76.50-125.00   0.00   50
 16  ω     59.00  84.00   0.50    0.20    --   76.50 -95.00   0.00   50
 17  ω     29.00  56.00   0.50    0.20    --   63.61 -95.00   0.00   54
 18  ω     39.00  75.00   0.50    0.20    --   75.71 -95.00 -30.00   72
 19  ω     38.00  72.00   0.50    0.20    --   63.61 -95.00-150.00   68
 20  ω     39.00  64.00   0.50    0.20    --   76.50 -95.00-120.00   50
 21  ω     43.00  84.00   0.50    0.20    --   76.50 -95.00 -90.00   82
 22  ω     54.00  82.00   0.50    0.20    --   76.50 -95.00 -60.00   56
 23  ω     41.00  73.00   0.50    0.20    --   76.50 -95.00  30.00   64
 24  ω    -67.00 -40.00   0.50    0.20    --  -64.68   0.00 -30.00   54
 25  ω    -70.00 -43.00   0.50    0.20    --  -71.11   0.00  60.00   54
 26  ω    -72.00 -36.00   0.50    0.20    --  -71.11   0.00   0.00   72
 27  ω    -67.00 -34.00   0.50    0.20    --  -71.11   0.00 -60.00   66
 28  ω    -68.00 -38.00   0.50    0.20    --  -71.11   0.00-150.00   60
 29  ω   -106.00 -80.00   0.50    0.20    --  -76.25 -85.00 -81.27   52
 30  ω   -111.00 -82.00   0.50    0.20    --  -76.25 -87.00  30.99   58
 31  ω    -97.00 -46.00   0.50    0.20    --  -71.11 125.00  30.00  102
 32  ω    -95.00 -40.00   0.50    0.20    --  -71.11 125.00-120.00  110
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW 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      -0.0487025000
_diffrn_orient_matrix_UB_12      0.0459208000
_diffrn_orient_matrix_UB_13      0.0229239000
_diffrn_orient_matrix_UB_21      -0.0290124000
_diffrn_orient_matrix_UB_22      -0.1436591000
_diffrn_orient_matrix_UB_23      -0.0230535000
_diffrn_orient_matrix_UB_31      0.0312077000
_diffrn_orient_matrix_UB_32      -0.0619164000
_diffrn_orient_matrix_UB_33      0.0705201000
_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                3952
_reflns_number_total             4842
_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 1.171.43.94a (Rigaku OD, 2023)'
_computing_data_collection       
'CrysAlisPro system (CCD 43.94a 64-bit (release 20-10-2023))'
_computing_data_reduction        'CrysAlisPro 1.171.43.94a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT 2018/2 (Sheldrick, 2015)'
_refine_diff_density_max         0.320
_refine_diff_density_min         -0.390
_refine_diff_density_rms         0.046
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     335
_refine_ls_number_reflns         4842
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0514
_refine_ls_R_factor_gt           0.0413
_refine_ls_restrained_S_all      1.050
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0574P)²+3.0579P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1062
_refine_ls_wR_factor_ref         0.1121
_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 Ternary CH refined with riding coordinates:
 C3(H3), C5(H5)
2.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C6(H6A,H6B)
2.c Aromatic/amide H refined with riding coordinates:
 C8(H8), C9(H9), C10(H10), C11(H11), C12(H12), C15(H15), C16(H16), C17(H17),
 C18(H18), C19(H19), C23(H23), C24(H24), C26(H26), C27(H27)
2.d Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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_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 0.71850(4) -0.06218(11) 0.48458(4) 0.0389(2) Uani 1 1 d . . . . .
F2 F 0.68689(5) -0.22688(11) 0.41096(5) 0.0485(3) Uani 1 1 d . . . . .
F3 F 0.63064(4) -0.11259(12) 0.44843(5) 0.0432(3) Uani 1 1 d . . . . .
O1 O 0.66028(4) 0.14309(11) 0.39955(5) 0.0266(2) Uani 1 1 d . . . . .
O2 O 0.48803(5) 0.27521(14) 0.32764(6) 0.0360(3) Uani 1 1 d . . . . .
O3 O 0.50949(4) 0.37975(13) 0.42865(5) 0.0307(3) Uani 1 1 d . . . . .
O4 O 0.81926(5) 0.68866(14) 0.34347(6) 0.0407(3) Uani 1 1 d . . . . .
O5 O 0.75689(7) 0.7828(2) 0.25692(8) 0.0750(6) Uani 1 1 d . . . . .
N1 N 0.61694(5) -0.02525(14) 0.31633(6) 0.0259(3) Uani 1 1 d . . . . .
N2 N 0.77139(7) 0.69610(16) 0.30308(7) 0.0365(3) Uani 1 1 d . . . . .
C1 C 0.60569(6) 0.19235(16) 0.36231(7) 0.0240(3) Uani 1 1 d . . . . .
C2 C 0.58485(6) 0.31157(16) 0.39524(7) 0.0234(3) Uani 1 1 d . . . . .
C3 C 0.60045(6) 0.33568(16) 0.33065(7) 0.0241(3) Uani 1 1 d . . . . .
H3 H 0.566470 0.343674 0.288875 0.029 Uiso 1 1 calc R U . . .
C4 C 0.57276(6) 0.06497(16) 0.32578(7) 0.0263(3) Uani 1 1 d . . . . .
H4A H 0.553778 0.016502 0.353369 0.032 Uiso 1 1 calc R U . . .
H4B H 0.544404 0.092309 0.281930 0.032 Uiso 1 1 calc R U . . .
C5 C 0.66652(6) 0.00747(16) 0.37308(7) 0.0250(3) Uani 1 1 d . . . . .
H5 H 0.700021 0.008093 0.358644 0.030 Uiso 1 1 calc R U . . .
C6 C 0.62320(7) -0.00323(18) 0.25044(7) 0.0302(3) Uani 1 1 d . . . . .
H6A H 0.661009 -0.035037 0.253007 0.036 Uiso 1 1 calc R U . . .
H6B H 0.620095 0.099101 0.239713 0.036 Uiso 1 1 calc R U . . .
C7 C 0.57932(7) -0.08286(17) 0.19460(8) 0.0293(3) Uani 1 1 d . . . . .
C8 C 0.57079(8) -0.0502(2) 0.12754(8) 0.0414(4) Uani 1 1 d . . . . .
H8 H 0.591208 0.025071 0.117171 0.050 Uiso 1 1 calc R U . . .
C9 C 0.53257(9) -0.1272(3) 0.07577(9) 0.0511(5) Uani 1 1 d . . . . .
H9 H 0.527526 -0.105208 0.030217 0.061 Uiso 1 1 calc R U . . .
C10 C 0.50191(9) -0.2350(2) 0.08988(10) 0.0484(5) Uani 1 1 d . . . . .
H10 H 0.475597 -0.286741 0.054263 0.058 Uiso 1 1 calc R U . . .
C11 C 0.50966(8) -0.2672(2) 0.15581(9) 0.0418(4) Uani 1 1 d . . . . .
H11 H 0.488438 -0.341110 0.165773 0.050 Uiso 1 1 calc R U . . .
C12 C 0.54839(7) -0.19220(18) 0.20807(8) 0.0336(4) Uani 1 1 d . . . . .
H12 H 0.553711 -0.216133 0.253492 0.040 Uiso 1 1 calc R U . . .
C13 C 0.67535(7) -0.09890(17) 0.42962(8) 0.0303(3) Uani 1 1 d . . . . .
C14 C 0.62115(6) 0.36659(16) 0.46295(7) 0.0234(3) Uani 1 1 d . . . . .
C15 C 0.63969(7) 0.27537(17) 0.51799(8) 0.0294(3) Uani 1 1 d . . . . .
H15 H 0.632339 0.176810 0.511740 0.035 Uiso 1 1 calc R U . . .
C16 C 0.66887(7) 0.32778(19) 0.58193(8) 0.0329(4) Uani 1 1 d . . . . .
H16 H 0.681506 0.264994 0.619278 0.039 Uiso 1 1 calc R U . . .
C17 C 0.67963(7) 0.47163(19) 0.59146(8) 0.0316(4) Uani 1 1 d . . . . .
H17 H 0.698862 0.507620 0.635418 0.038 Uiso 1 1 calc R U . . .
C18 C 0.66227(7) 0.56270(18) 0.53674(8) 0.0305(3) Uani 1 1 d . . . . .
H18 H 0.670334 0.660956 0.543006 0.037 Uiso 1 1 calc R U . . .
C19 C 0.63299(6) 0.51017(17) 0.47256(7) 0.0264(3) Uani 1 1 d . . . . .
H19 H 0.621043 0.572880 0.435138 0.032 Uiso 1 1 calc R U . . .
C20 C 0.52264(6) 0.31773(17) 0.37947(7) 0.0257(3) Uani 1 1 d . . . . .
C21 C 0.45031(7) 0.3966(2) 0.41651(8) 0.0358(4) Uani 1 1 d . . . . .
H21A H 0.432361 0.444374 0.373176 0.054 Uiso 1 1 calc R U . . .
H21B H 0.445290 0.453546 0.452695 0.054 Uiso 1 1 calc R U . . .
H21C H 0.433113 0.303398 0.415395 0.054 Uiso 1 1 calc R U . . .
C22 C 0.64749(6) 0.42494(16) 0.32752(7) 0.0234(3) Uani 1 1 d . . . . .
C23 C 0.63458(7) 0.51975(17) 0.27350(7) 0.0277(3) Uani 1 1 d . . . . .
H23 H 0.597261 0.523483 0.242082 0.033 Uiso 1 1 calc R U . . .
C24 C 0.67473(7) 0.60803(17) 0.26470(8) 0.0306(3) Uani 1 1 d . . . . .
H24 H 0.665397 0.672730 0.228068 0.037 Uiso 1 1 calc R U . . .
C25 C 0.72860(7) 0.59986(17) 0.31034(8) 0.0277(3) Uani 1 1 d . . . . .
C26 C 0.74351(7) 0.50646(16) 0.36415(7) 0.0268(3) Uani 1 1 d . . . . .
H26 H 0.781170 0.501983 0.394583 0.032 Uiso 1 1 calc R U . . .
C27 C 0.70272(7) 0.41977(16) 0.37290(7) 0.0260(3) Uani 1 1 d . . . . .
H27 H 0.712314 0.356288 0.410018 0.031 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 C13 1.3362(18) . ?
F2 C13 1.3360(18) . ?
F3 C13 1.335(2) . ?
O1 C1 1.4140(17) . ?
O1 C5 1.4294(17) . ?
O2 C20 1.2102(18) . ?
O3 C20 1.3346(18) . ?
O3 C21 1.4435(19) . ?
O4 N2 1.2203(19) . ?
O5 N2 1.228(2) . ?
N1 C4 1.478(2) . ?
N1 C5 1.4384(18) . ?
N1 C6 1.4724(19) . ?
N2 C25 1.466(2) . ?
C1 C2 1.514(2) . ?
C1 C3 1.496(2) . ?
C1 C4 1.515(2) . ?
C2 C3 1.567(2) . ?
C2 C14 1.5004(19) . ?
C2 C20 1.499(2) . ?
C3 H3 1.0000 . ?
C3 C22 1.483(2) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 H5 1.0000 . ?
C5 C13 1.518(2) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C6 C7 1.512(2) . ?
C7 C8 1.393(2) . ?
C7 C12 1.387(2) . ?
C8 H8 0.9500 . ?
C8 C9 1.389(3) . ?
C9 H9 0.9500 . ?
C9 C10 1.377(3) . ?
C10 H10 0.9500 . ?
C10 C11 1.373(3) . ?
C11 H11 0.9500 . ?
C11 C12 1.391(2) . ?
C12 H12 0.9500 . ?
C14 C15 1.392(2) . ?
C14 C19 1.389(2) . ?
C15 H15 0.9500 . ?
C15 C16 1.388(2) . ?
C16 H16 0.9500 . ?
C16 C17 1.387(2) . ?
C17 H17 0.9500 . ?
C17 C18 1.385(2) . ?
C18 H18 0.9500 . ?
C18 C19 1.393(2) . ?
C19 H19 0.9500 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 C23 1.398(2) . ?
C22 C27 1.398(2) . ?
C23 H23 0.9500 . ?
C23 C24 1.380(2) . ?
C24 H24 0.9500 . ?
C24 C25 1.375(2) . ?
C25 C26 1.385(2) . ?
C26 H26 0.9500 . ?
C26 C27 1.383(2) . ?
C27 H27 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
C1 O1 C5 107.35(11) . . ?
C20 O3 C21 116.01(12) . . ?
C5 N1 C4 104.40(11) . . ?
C5 N1 C6 114.05(12) . . ?
C6 N1 C4 112.64(12) . . ?
O4 N2 O5 122.98(15) . . ?
O4 N2 C25 119.03(14) . . ?
O5 N2 C25 117.97(15) . . ?
O1 C1 C2 114.90(12) . . ?
O1 C1 C3 117.65(12) . . ?
O1 C1 C4 106.42(12) . . ?
C2 C1 C4 127.32(13) . . ?
C3 C1 C2 62.74(10) . . ?
C3 C1 C4 122.94(12) . . ?
C1 C2 C3 58.06(9) . . ?
C14 C2 C1 120.00(13) . . ?
C14 C2 C3 121.60(12) . . ?
C20 C2 C1 115.95(12) . . ?
C20 C2 C3 111.63(12) . . ?
C20 C2 C14 116.65(12) . . ?
C1 C3 C2 59.19(9) . . ?
C1 C3 H3 112.2 . . ?
C2 C3 H3 112.2 . . ?
C22 C3 C1 125.99(13) . . ?
C22 C3 C2 125.09(12) . . ?
C22 C3 H3 112.2 . . ?
N1 C4 C1 102.52(12) . . ?
N1 C4 H4A 111.3 . . ?
N1 C4 H4B 111.3 . . ?
C1 C4 H4A 111.3 . . ?
C1 C4 H4B 111.3 . . ?
H4A C4 H4B 109.2 . . ?
O1 C5 N1 109.58(12) . . ?
O1 C5 H5 109.7 . . ?
O1 C5 C13 106.91(12) . . ?
N1 C5 H5 109.7 . . ?
N1 C5 C13 111.17(13) . . ?
C13 C5 H5 109.7 . . ?
N1 C6 H6A 109.2 . . ?
N1 C6 H6B 109.2 . . ?
N1 C6 C7 112.07(13) . . ?
H6A C6 H6B 107.9 . . ?
C7 C6 H6A 109.2 . . ?
C7 C6 H6B 109.2 . . ?
C8 C7 C6 119.72(16) . . ?
C12 C7 C6 121.77(14) . . ?
C12 C7 C8 118.47(16) . . ?
C7 C8 H8 119.9 . . ?
C9 C8 C7 120.29(19) . . ?
C9 C8 H8 119.9 . . ?
C8 C9 H9 119.7 . . ?
C10 C9 C8 120.61(18) . . ?
C10 C9 H9 119.7 . . ?
C9 C10 H10 120.2 . . ?
C11 C10 C9 119.53(18) . . ?
C11 C10 H10 120.2 . . ?
C10 C11 H11 119.8 . . ?
C10 C11 C12 120.38(19) . . ?
C12 C11 H11 119.8 . . ?
C7 C12 C11 120.71(17) . . ?
C7 C12 H12 119.6 . . ?
C11 C12 H12 119.6 . . ?
F1 C13 C5 111.39(13) . . ?
F2 C13 F1 107.10(13) . . ?
F2 C13 C5 110.72(13) . . ?
F3 C13 F1 106.91(13) . . ?
F3 C13 F2 107.33(14) . . ?
F3 C13 C5 113.09(13) . . ?
C15 C14 C2 120.00(14) . . ?
C19 C14 C2 120.52(13) . . ?
C19 C14 C15 119.30(14) . . ?
C14 C15 H15 119.9 . . ?
C16 C15 C14 120.29(15) . . ?
C16 C15 H15 119.9 . . ?
C15 C16 H16 119.9 . . ?
C17 C16 C15 120.17(15) . . ?
C17 C16 H16 119.9 . . ?
C16 C17 H17 120.1 . . ?
C18 C17 C16 119.87(15) . . ?
C18 C17 H17 120.1 . . ?
C17 C18 H18 120.0 . . ?
C17 C18 C19 119.97(15) . . ?
C19 C18 H18 120.0 . . ?
C14 C19 C18 120.37(15) . . ?
C14 C19 H19 119.8 . . ?
C18 C19 H19 119.8 . . ?
O2 C20 O3 123.50(14) . . ?
O2 C20 C2 124.43(14) . . ?
O3 C20 C2 112.03(12) . . ?
O3 C21 H21A 109.5 . . ?
O3 C21 H21B 109.5 . . ?
O3 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C23 C22 C3 115.99(13) . . ?
C27 C22 C3 125.53(13) . . ?
C27 C22 C23 118.48(14) . . ?
C22 C23 H23 119.2 . . ?
C24 C23 C22 121.61(15) . . ?
C24 C23 H23 119.2 . . ?
C23 C24 H24 120.9 . . ?
C25 C24 C23 118.24(14) . . ?
C25 C24 H24 120.9 . . ?
C24 C25 N2 118.99(14) . . ?
C24 C25 C26 122.21(15) . . ?
C26 C25 N2 118.78(15) . . ?
C25 C26 H26 120.5 . . ?
C27 C26 C25 119.00(15) . . ?
C27 C26 H26 120.5 . . ?
C22 C27 H27 119.8 . . ?
C26 C27 C22 120.46(14) . . ?
C26 C27 H27 119.8 . . ?

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
O1 C1 C2 C3 109.66(14) . . . . ?
O1 C1 C2 C14 -1.0(2) . . . . ?
O1 C1 C2 C20 -149.99(13) . . . . ?
O1 C1 C3 C2 -105.36(14) . . . . ?
O1 C1 C3 C22 7.9(2) . . . . ?
O1 C1 C4 N1 -28.90(14) . . . . ?
O1 C5 C13 F1 -55.05(17) . . . . ?
O1 C5 C13 F2 -174.11(12) . . . . ?
O1 C5 C13 F3 65.39(16) . . . . ?
O4 N2 C25 C24 -179.80(15) . . . . ?
O4 N2 C25 C26 2.0(2) . . . . ?
O5 N2 C25 C24 1.5(2) . . . . ?
O5 N2 C25 C26 -176.69(17) . . . . ?
N1 C5 C13 F1 -174.61(12) . . . . ?
N1 C5 C13 F2 66.32(17) . . . . ?
N1 C5 C13 F3 -54.17(17) . . . . ?
N1 C6 C7 C8 165.67(15) . . . . ?
N1 C6 C7 C12 -16.8(2) . . . . ?
N2 C25 C26 C27 177.20(14) . . . . ?
C1 O1 C5 N1 3.42(15) . . . . ?
C1 O1 C5 C13 -117.16(13) . . . . ?
C1 C2 C3 C22 -114.67(16) . . . . ?
C1 C2 C14 C15 -58.1(2) . . . . ?
C1 C2 C14 C19 126.85(16) . . . . ?
C1 C2 C20 O2 -28.6(2) . . . . ?
C1 C2 C20 O3 153.27(13) . . . . ?
C1 C3 C22 C23 152.89(14) . . . . ?
C1 C3 C22 C27 -26.0(2) . . . . ?
C2 C1 C3 C22 113.21(16) . . . . ?
C2 C1 C4 N1 -169.86(13) . . . . ?
C2 C3 C22 C23 -132.38(15) . . . . ?
C2 C3 C22 C27 48.7(2) . . . . ?
C2 C14 C15 C16 -174.02(15) . . . . ?
C2 C14 C19 C18 173.99(14) . . . . ?
C3 C1 C2 C14 -110.67(15) . . . . ?
C3 C1 C2 C20 100.35(14) . . . . ?
C3 C1 C4 N1 111.22(15) . . . . ?
C3 C2 C14 C15 -126.90(15) . . . . ?
C3 C2 C14 C19 58.1(2) . . . . ?
C3 C2 C20 O2 35.3(2) . . . . ?
C3 C2 C20 O3 -142.82(13) . . . . ?
C3 C22 C23 C24 -179.60(14) . . . . ?
C3 C22 C27 C26 178.67(14) . . . . ?
C4 N1 C5 O1 -21.86(15) . . . . ?
C4 N1 C5 C13 96.09(14) . . . . ?
C4 N1 C6 C7 -80.59(16) . . . . ?
C4 C1 C2 C3 -112.11(17) . . . . ?
C4 C1 C2 C14 137.22(15) . . . . ?
C4 C1 C2 C20 -11.8(2) . . . . ?
C4 C1 C3 C2 118.61(16) . . . . ?
C4 C1 C3 C22 -128.17(16) . . . . ?
C5 O1 C1 C2 162.63(12) . . . . ?
C5 O1 C1 C3 -126.45(13) . . . . ?
C5 O1 C1 C4 16.15(15) . . . . ?
C5 N1 C4 C1 30.16(14) . . . . ?
C5 N1 C6 C7 160.65(13) . . . . ?
C6 N1 C4 C1 -94.10(14) . . . . ?
C6 N1 C5 O1 101.49(14) . . . . ?
C6 N1 C5 C13 -140.56(13) . . . . ?
C6 C7 C8 C9 176.84(17) . . . . ?
C6 C7 C12 C11 -177.71(16) . . . . ?
C7 C8 C9 C10 1.1(3) . . . . ?
C8 C7 C12 C11 -0.2(3) . . . . ?
C8 C9 C10 C11 -0.5(3) . . . . ?
C9 C10 C11 C12 -0.4(3) . . . . ?
C10 C11 C12 C7 0.7(3) . . . . ?
C12 C7 C8 C9 -0.8(3) . . . . ?
C14 C2 C3 C1 107.95(15) . . . . ?
C14 C2 C3 C22 -6.7(2) . . . . ?
C14 C2 C20 O2 -178.61(15) . . . . ?
C14 C2 C20 O3 3.23(19) . . . . ?
C14 C15 C16 C17 0.2(2) . . . . ?
C15 C14 C19 C18 -1.1(2) . . . . ?
C15 C16 C17 C18 -1.4(3) . . . . ?
C16 C17 C18 C19 1.4(2) . . . . ?
C17 C18 C19 C14 -0.2(2) . . . . ?
C19 C14 C15 C16 1.1(2) . . . . ?
C20 C2 C3 C1 -107.91(14) . . . . ?
C20 C2 C3 C22 137.42(15) . . . . ?
C20 C2 C14 C15 90.64(18) . . . . ?
C20 C2 C14 C19 -84.38(18) . . . . ?
C21 O3 C20 O2 -1.0(2) . . . . ?
C21 O3 C20 C2 177.14(13) . . . . ?
C22 C23 C24 C25 0.7(2) . . . . ?
C23 C22 C27 C26 -0.2(2) . . . . ?
C23 C24 C25 N2 -178.00(14) . . . . ?
C23 C24 C25 C26 0.1(2) . . . . ?
C24 C25 C26 C27 -0.9(2) . . . . ?
C25 C26 C27 C22 1.0(2) . . . . ?
C27 C22 C23 C24 -0.6(2) . . . . ?

_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
- Detector area scaling
- B-factor correction
;
_oxdiff_exptl_absorpt_empirical_full_max 1.270
_oxdiff_exptl_absorpt_empirical_full_min 0.823
####################################################################### 
# 
# 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_dkb-01-695
_database_code_depnum_ccdc_archive 'CCDC 2451793'
loop_
_audit_author_name
_audit_author_address
'Farzaneh Fadaei Tirani'
;EPFL
Switzerland
;
_audit_update_record             
;
2025-05-16 deposited with the CCDC.	2026-01-07 downloaded from the CCDC.
;
_audit_creation_date             2025-05-05
_audit_creation_method           
;
Olex2 1.5
(compiled 2025.04.05 svn.rf049d14d for OlexSys, GUI svn.r7224)
;
_shelx_SHELXL_version_number     2019/3
_audit_contact_author            'Farzaneh Fadaei Tirani'
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H17 F6 N O3'
_chemical_formula_sum            'C21 H17 F6 N O3'
_chemical_formula_weight         445.36
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C21 H17 F6 N O3'
_chemical_oxdiff_usercomment     'EtOAc, Toluene, Pentane'
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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   14.77504(10)
_cell_length_b                   24.62736(17)
_cell_length_c                   11.15008(6)
_cell_angle_alpha                90
_cell_angle_beta                 90.3773(6)
_cell_angle_gamma                90
_cell_volume                     4057.09(5)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    37169
_cell_measurement_temperature    140.00(10)
_cell_measurement_theta_max      75.0720
_cell_measurement_theta_min      2.9840
_shelx_estimated_absorpt_T_max   0.933
_shelx_estimated_absorpt_T_min   0.757
_exptl_absorpt_coefficient_mu    1.178
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.591
_exptl_absorpt_correction_type   Gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.143a (Rigaku Oxford Diffraction, 2024)
Numerical absorption correction based on Gaussian integration over
a multifaceted crystal model.
Empirical absorption correction using spherical harmonics
as implemented in SCALE3 ABSPACK scaling algorithm
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.458
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1824
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 -1 0 0.0302
0 1 0 0.0306
-1 0 0 0.1303
1 0 0 0.1170
0 0 -1 0.0745
0 0 1 0.0809
0 -1 1 0.0632
-1 1 2 0.0834
-1 -1 -2 0.0823

_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.06
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
0.0000 -1.0000 0.0000 0.0013 0.0613 0.0126
-0.0000 1.0000 -0.0000 -0.0013 -0.0613 -0.0126
-1.0000 -0.0000 0.0000 -0.1027 -0.0016 0.0182
1.0000 0.0000 -0.0000 0.1027 0.0016 -0.0182
-0.0000 -0.0000 -1.0000 0.0232 -0.0279 0.1333
0.0000 0.0000 1.0000 -0.0232 0.0279 -0.1333
0.0000 -1.0000 1.0000 -0.0220 0.0892 -0.1207
-1.0000 1.0000 2.0000 -0.1504 -0.0071 -0.2609
-1.0000 -1.0000 -2.0000 -0.0550 0.0038 0.2974

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0170
_diffrn_reflns_av_unetI/netI     0.0110
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            54330
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.363
_diffrn_reflns_theta_min         2.991
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      140.00(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 0.999
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     89.00 117.00   0.50    0.20    --   79.75  21.00  17.60   56
  2  ω     65.00  95.00   0.50    0.20    --   79.75  20.00  -9.50   60
  3  ω     58.00  94.00   0.50    0.20    --   79.75  20.00 -45.66   72
  4  ω     77.00 103.00   0.50    0.20    --   79.75  23.00 -92.89   52
  5  ω     64.00  89.00   0.50    0.20    --   79.75  21.00-102.48   50
  6  ω     46.00 108.00   0.50    0.20    --   79.75   9.00-132.22  124
  7  ω     51.00  76.00   0.50    0.20    --   76.61  15.00   0.00   50
  8  ω     46.00  92.00   0.50    0.20    --   79.75   4.00 -46.34   92
  9  ω     86.00 114.00   0.50    0.20    --   76.61  15.00   0.00   56
 10  ω     70.00 119.00   0.50    0.20    --   79.75   7.00  -3.71   98
 11  ω     70.00 111.00   0.50    0.20    --   79.75   8.00  51.81   82
 12  ω     55.00 101.00   0.50    0.20    --   79.75   9.00 153.60   92
 13  ω     46.00  71.00   0.50    0.20    --   79.75 -64.00  -1.15   50
 14  ω     45.00 100.00   0.50    0.20    --   79.75-114.00 -33.51  110
 15  ω     71.00  98.00   0.50    0.20    --   76.61-125.00-180.00   54
 16  ω     39.00  65.00   0.50    0.20    --   75.73-111.00-137.00   52
 17  ω     27.00  81.00   0.50    0.20    --   63.87-111.00-137.00  108
 18  ω     65.00  90.00   0.50    0.20    --   76.61-111.00-137.00   50
 19  ω     77.00 102.00   0.50    0.20    --   76.61-125.00 -90.00   50
 20  ω     43.00  81.00   0.50    0.20    --   76.61 -95.00 -90.00   76
 21  ω     37.00  82.00   0.50    0.20    --   75.73-111.00-120.00   90
 22  ω     45.00  85.00   0.50    0.20    --   76.61 -95.00-120.00   80
 23  ω     78.00 103.00   0.50    0.20    --   76.61-125.00 -60.00   50
 24  ω     39.00  81.00   0.50    0.20    --   76.61 -95.00 -30.00   84
 25  ω     63.00  89.00   0.50    0.20    --   75.73-111.00   0.00   52
 26  ω     48.00  73.00   0.50    0.20    --   76.61 -95.00  60.00   50
 27  ω     51.00  83.00   0.50    0.20    --   76.61 -95.00  30.00   64
 28  ω     46.00  79.00   0.50    0.20    --   76.61 -95.00   0.00   66
 29  ω     26.00  64.00   0.50    0.20    --   63.87 -95.00  60.00   76
 30  ω     78.00 103.00   0.50    0.20    --   76.61-125.00 150.00   50
 31  ω     47.00  72.00   0.50    0.20    --   63.87 -95.00 120.00   50
 32  ω   -111.00 -86.00   0.50    0.20    --  -76.25 -75.00 -90.15   50
 33  ω   -111.00 -85.00   0.50    0.20    --  -76.25 -82.00 -92.48   52
 34  ω   -109.00 -82.00   0.50    0.20    --  -76.25 -81.00-176.69   54
 35  ω   -109.00 -84.00   0.50    0.20    --  -76.25 -87.00 -18.32   50
 36  ω   -112.00 -85.00   0.50    0.20    --  -76.25 -96.00 132.42   54
 37  ω    -71.00 -36.00   0.50    0.20    --  -71.12   0.00 150.00   70
 38  ω    -66.00 -38.00   0.50    0.20    --  -71.12   0.00  90.00   56
 39  ω    -65.00 -34.00   0.50    0.20    --  -71.12   0.00 -60.00   62
 40  ω    -67.00 -42.00   0.50    0.20    --  -71.12   0.00-120.00   50
 41  ω    -84.00 -59.00   0.50    0.20    --  -71.12 111.00 -44.00   50
 42  ω    -71.00 -32.00   0.50    0.20    --  -64.59 111.00 -44.00   78
 43  ω    -67.00 -34.00   0.50    0.20    --  -76.25 136.00-157.16   66
 44  ω    -87.00 -45.00   0.50    0.20    --  -71.12 111.00-120.00   84
 45  ω   -111.00 -78.00   0.50    0.20    --  -76.25 136.00-157.16   66
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW 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      0.1026749000
_diffrn_orient_matrix_UB_12      -0.0012558000
_diffrn_orient_matrix_UB_13      -0.0232295000
_diffrn_orient_matrix_UB_21      0.0016479000
_diffrn_orient_matrix_UB_22      -0.0612639000
_diffrn_orient_matrix_UB_23      0.0279262000
_diffrn_orient_matrix_UB_31      -0.0182367000
_diffrn_orient_matrix_UB_32      -0.0125799000
_diffrn_orient_matrix_UB_33      -0.1332748000
_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                7455
_reflns_number_total             8257
_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 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT 2018/2 (Sheldrick, 2015)'
_refine_diff_density_max         0.290
_refine_diff_density_min         -0.200
_refine_diff_density_rms         0.033
_refine_ls_extinction_coef       0.00060(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2019/2 (Sheldrick 2019)'
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     570
_refine_ls_number_reflns         8257
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0336
_refine_ls_R_factor_gt           0.0304
_refine_ls_restrained_S_all      1.013
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0359P)²+1.3525P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0768
_refine_ls_wR_factor_ref         0.0786
_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 Ternary CH refined with riding coordinates:
 C3(H3), C4(H4), C24(H24), C25(H25)
2.b Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B), C26(H26A,H26B)
2.c Aromatic/amide H refined with riding coordinates:
 C9(H9), C10(H10), C11(H11), C12(H12), C13(H13), C15(H15), C16(H16), C18(H18),
 C19(H19), C30(H30), C31(H31), C32(H32), C33(H33), C34(H34), C36(H36), C37(H37),
  C39(H39), C40(H40)
2.d Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C), C42(H42A,H42B,H42C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_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_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 1.12892(6) 0.50424(3) 0.28522(8) 0.0500(2) Uani 1 1 d . . . . .
F2 F 0.98790(5) 0.48466(3) 0.30155(6) 0.03625(16) Uani 1 1 d . . . . .
F3 F 1.06703(6) 0.44788(3) 0.16200(6) 0.04231(18) Uani 1 1 d . . . . .
F4 F 0.78028(5) 0.41871(3) 0.45597(7) 0.03729(17) Uani 1 1 d . . . . .
F5 F 0.82983(5) 0.37528(3) 0.61048(6) 0.03682(17) Uani 1 1 d . . . . .
F6 F 0.73264(5) 0.33792(3) 0.49249(6) 0.03648(17) Uani 1 1 d . . . . .
O1 O 1.02946(5) 0.37509(3) 0.33689(7) 0.02766(17) Uani 1 1 d . . . . .
O2 O 1.16072(6) 0.10949(4) 0.22671(7) 0.0361(2) Uani 1 1 d . . . . .
O3 O 1.12332(6) 0.07556(3) 0.40587(7) 0.03328(19) Uani 1 1 d . . . . .
N1 N 1.08869(7) 0.43337(4) 0.48301(9) 0.0325(2) Uani 1 1 d . . . . .
H1 H 1.1297(11) 0.4173(6) 0.5256(14) 0.042(4) Uiso 1 1 d . . . . .
C1 C 0.97474(7) 0.36950(4) 0.43968(9) 0.0245(2) Uani 1 1 d . . . . .
C2 C 0.88159(7) 0.34697(4) 0.41805(9) 0.0231(2) Uani 1 1 d . . . . .
C3 C 0.95453(7) 0.31277(5) 0.48344(9) 0.0247(2) Uani 1 1 d . . . . .
H3 H 0.945046 0.311110 0.572083 0.030 Uiso 1 1 calc R U . . .
C4 C 1.09422(7) 0.41717(5) 0.35996(11) 0.0298(2) Uani 1 1 d . . . . .
H4 H 1.156617 0.403901 0.341850 0.036 Uiso 1 1 calc R U . . .
C5 C 0.99792(8) 0.41710(5) 0.52200(10) 0.0294(2) Uani 1 1 d . . . . .
H5A H 0.954075 0.447153 0.511561 0.035 Uiso 1 1 calc R U . . .
H5B H 0.998488 0.405701 0.607150 0.035 Uiso 1 1 calc R U . . .
C6 C 1.06933(8) 0.46363(5) 0.27672(11) 0.0325(3) Uani 1 1 d . . . . .
C7 C 0.80666(8) 0.36943(5) 0.49449(10) 0.0281(2) Uani 1 1 d . . . . .
C8 C 0.84787(7) 0.33340(4) 0.29438(9) 0.0232(2) Uani 1 1 d . . . . .
C9 C 0.84733(7) 0.37287(5) 0.20487(10) 0.0265(2) Uani 1 1 d . . . . .
H9 H 0.874704 0.407175 0.219288 0.032 Uiso 1 1 calc R U . . .
C10 C 0.80683(8) 0.36216(5) 0.09452(11) 0.0325(3) Uani 1 1 d . . . . .
H10 H 0.806688 0.389094 0.033533 0.039 Uiso 1 1 calc R U . . .
C11 C 0.76678(8) 0.31235(6) 0.07356(11) 0.0361(3) Uani 1 1 d . . . . .
H11 H 0.738432 0.305276 -0.001547 0.043 Uiso 1 1 calc R U . . .
C12 C 0.76779(8) 0.27274(5) 0.16140(12) 0.0363(3) Uani 1 1 d . . . . .
H12 H 0.740656 0.238423 0.146335 0.044 Uiso 1 1 calc R U . . .
C13 C 0.80850(8) 0.28312(5) 0.27176(11) 0.0298(2) Uani 1 1 d . . . . .
H13 H 0.809419 0.255798 0.331897 0.036 Uiso 1 1 calc R U . . .
C14 C 0.99457(7) 0.26184(4) 0.43436(9) 0.0232(2) Uani 1 1 d . . . . .
C15 C 0.99437(7) 0.21620(5) 0.50845(10) 0.0254(2) Uani 1 1 d . . . . .
H15 H 0.965751 0.218255 0.584362 0.030 Uiso 1 1 calc R U . . .
C16 C 1.03481(7) 0.16802(5) 0.47415(10) 0.0260(2) Uani 1 1 d . . . . .
H16 H 1.034564 0.137642 0.526654 0.031 Uiso 1 1 calc R U . . .
C17 C 1.07595(7) 0.16421(4) 0.36220(9) 0.0232(2) Uani 1 1 d . . . . .
C18 C 1.07427(7) 0.20903(5) 0.28617(9) 0.0258(2) Uani 1 1 d . . . . .
H18 H 1.100657 0.206395 0.208924 0.031 Uiso 1 1 calc R U . . .
C19 C 1.03477(8) 0.25740(5) 0.32136(10) 0.0265(2) Uani 1 1 d . . . . .
H19 H 1.034929 0.287708 0.268649 0.032 Uiso 1 1 calc R U . . .
C20 C 1.12418(7) 0.11431(5) 0.32257(10) 0.0253(2) Uani 1 1 d . . . . .
C21 C 1.17217(10) 0.02635(5) 0.37839(13) 0.0399(3) Uani 1 1 d . . . . .
H21A H 1.155089 0.013762 0.297996 0.060 Uiso 1 1 calc R U . . .
H21B H 1.157194 -0.001686 0.437399 0.060 Uiso 1 1 calc R U . . .
H21C H 1.237376 0.033581 0.381144 0.060 Uiso 1 1 calc R U . . .
F7 F 0.58653(6) 0.45726(4) 0.43522(7) 0.0470(2) Uani 1 1 d . . . . .
F8 F 0.52349(6) 0.50392(4) 0.29516(8) 0.0559(2) Uani 1 1 d . . . . .
F9 F 0.66866(6) 0.50344(4) 0.31434(9) 0.0557(2) Uani 1 1 d . . . . .
F10 F 0.27172(5) 0.42717(3) 0.13879(7) 0.03836(17) Uani 1 1 d . . . . .
F11 F 0.33307(5) 0.39070(3) -0.01575(6) 0.04231(19) Uani 1 1 d . . . . .
F12 F 0.23780(5) 0.34544(3) 0.08822(7) 0.04312(19) Uani 1 1 d . . . . .
O4 O 0.52623(5) 0.38959(3) 0.26479(7) 0.03059(18) Uani 1 1 d . . . . .
O5 O 0.64328(7) 0.11983(4) 0.38410(8) 0.0417(2) Uani 1 1 d . . . . .
O6 O 0.62617(6) 0.08998(3) 0.19587(8) 0.03322(19) Uani 1 1 d . . . . .
N2 N 0.59592(7) 0.44000(5) 0.11351(10) 0.0349(2) Uani 1 1 d . . . . .
H2 H 0.6298(11) 0.4192(7) 0.0690(15) 0.048(4) Uiso 1 1 d . . . . .
C22 C 0.47436(7) 0.38308(5) 0.15892(10) 0.0267(2) Uani 1 1 d . . . . .
C23 C 0.38130(7) 0.35980(5) 0.17657(10) 0.0251(2) Uani 1 1 d . . . . .
C24 C 0.45581(7) 0.32629(5) 0.11364(10) 0.0262(2) Uani 1 1 d . . . . .
H24 H 0.447456 0.324838 0.024621 0.031 Uiso 1 1 calc R U . . .
C25 C 0.60167(8) 0.42408(5) 0.23731(11) 0.0314(3) Uani 1 1 d . . . . .
H25 H 0.659690 0.404255 0.252477 0.038 Uiso 1 1 calc R U . . .
C26 C 0.50136(8) 0.42984(5) 0.07769(11) 0.0325(3) Uani 1 1 d . . . . .
H26A H 0.496943 0.419415 -0.007897 0.039 Uiso 1 1 calc R U . . .
H26B H 0.463085 0.462173 0.091838 0.039 Uiso 1 1 calc R U . . .
C27 C 0.59467(9) 0.47246(6) 0.32112(12) 0.0385(3) Uani 1 1 d . . . . .
C28 C 0.30654(8) 0.38054(5) 0.09668(11) 0.0298(2) Uani 1 1 d . . . . .
C29 C 0.34730(7) 0.34489(5) 0.29895(10) 0.0253(2) Uani 1 1 d . . . . .
C30 C 0.35002(8) 0.38256(5) 0.39228(10) 0.0286(2) Uani 1 1 d . . . . .
H30 H 0.378093 0.416831 0.380504 0.034 Uiso 1 1 calc R U . . .
C31 C 0.31172(8) 0.37009(5) 0.50268(11) 0.0337(3) Uani 1 1 d . . . . .
H31 H 0.313815 0.395802 0.566143 0.040 Uiso 1 1 calc R U . . .
C32 C 0.27074(8) 0.32040(6) 0.51987(11) 0.0369(3) Uani 1 1 d . . . . .
H32 H 0.244326 0.312068 0.595110 0.044 Uiso 1 1 calc R U . . .
C33 C 0.26790(8) 0.28261(6) 0.42805(12) 0.0371(3) Uani 1 1 d . . . . .
H33 H 0.239685 0.248412 0.440246 0.045 Uiso 1 1 calc R U . . .
C34 C 0.30646(8) 0.29484(5) 0.31792(11) 0.0312(2) Uani 1 1 d . . . . .
H34 H 0.304876 0.268763 0.255153 0.037 Uiso 1 1 calc R U . . .
C35 C 0.49412(7) 0.27511(5) 0.16363(9) 0.0246(2) Uani 1 1 d . . . . .
C36 C 0.49233(7) 0.22916(5) 0.09052(10) 0.0260(2) Uani 1 1 d . . . . .
H36 H 0.463856 0.231263 0.014027 0.031 Uiso 1 1 calc R U . . .
C37 C 0.53099(7) 0.18056(5) 0.12654(10) 0.0267(2) Uani 1 1 d . . . . .
H37 H 0.530164 0.150000 0.074557 0.032 Uiso 1 1 calc R U . . .
C38 C 0.57115(7) 0.17687(5) 0.23977(10) 0.0249(2) Uani 1 1 d . . . . .
C39 C 0.57044(8) 0.22186(5) 0.31508(10) 0.0284(2) Uani 1 1 d . . . . .
H39 H 0.595976 0.219078 0.393258 0.034 Uiso 1 1 calc R U . . .
C40 C 0.53313(8) 0.27063(5) 0.27796(10) 0.0290(2) Uani 1 1 d . . . . .
H40 H 0.533996 0.301127 0.330139 0.035 Uiso 1 1 calc R U . . .
C41 C 0.61655(7) 0.12663(5) 0.28239(10) 0.0271(2) Uani 1 1 d . . . . .
C42 C 0.67422(9) 0.04129(5) 0.22939(14) 0.0412(3) Uani 1 1 d . . . . .
H42A H 0.682704 0.018446 0.158374 0.062 Uiso 1 1 calc R U . . .
H42B H 0.639219 0.021300 0.289296 0.062 Uiso 1 1 calc R U . . .
H42C H 0.733399 0.051010 0.263288 0.062 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 C6 1.3353(14) . ?
F2 C6 1.3404(14) . ?
F3 C6 1.3368(14) . ?
F4 C7 1.3442(13) . ?
F5 C7 1.3434(13) . ?
F6 C7 1.3412(14) . ?
O1 C1 1.4137(13) . ?
O1 C4 1.4325(13) . ?
O2 C20 1.2064(14) . ?
O3 C20 1.3318(14) . ?
O3 C21 1.4444(14) . ?
N1 H1 0.863(16) . ?
N1 C4 1.4318(15) . ?
N1 C5 1.4683(15) . ?
C1 C2 1.5019(15) . ?
C1 C3 1.5102(16) . ?
C1 C5 1.5264(15) . ?
C2 C3 1.5466(14) . ?
C2 C7 1.5068(15) . ?
C2 C8 1.5007(14) . ?
C3 H3 1.0000 . ?
C3 C14 1.4923(14) . ?
C4 H4 1.0000 . ?
C4 C6 1.5170(18) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C8 C9 1.3930(16) . ?
C8 C13 1.3905(16) . ?
C9 H9 0.9500 . ?
C9 C10 1.3899(16) . ?
C10 H10 0.9500 . ?
C10 C11 1.3812(19) . ?
C11 H11 0.9500 . ?
C11 C12 1.382(2) . ?
C12 H12 0.9500 . ?
C12 C13 1.3898(17) . ?
C13 H13 0.9500 . ?
C14 C15 1.3950(15) . ?
C14 C19 1.4007(15) . ?
C15 H15 0.9500 . ?
C15 C16 1.3835(15) . ?
C16 H16 0.9500 . ?
C16 C17 1.3952(15) . ?
C17 C18 1.3920(15) . ?
C17 C20 1.4891(15) . ?
C18 H18 0.9500 . ?
C18 C19 1.3844(15) . ?
C19 H19 0.9500 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
F7 C27 1.3323(16) . ?
F8 C27 1.3364(15) . ?
F9 C27 1.3358(15) . ?
F10 C28 1.3443(13) . ?
F11 C28 1.3395(14) . ?
F12 C28 1.3365(14) . ?
O4 C22 1.4122(13) . ?
O4 C25 1.4360(14) . ?
O5 C41 1.2101(14) . ?
O6 C41 1.3294(14) . ?
O6 C42 1.4417(14) . ?
N2 H2 0.873(17) . ?
N2 C25 1.4370(16) . ?
N2 C26 1.4719(16) . ?
C22 C23 1.5038(15) . ?
C22 C24 1.5114(16) . ?
C22 C26 1.5200(16) . ?
C23 C24 1.5477(15) . ?
C23 C28 1.5039(15) . ?
C23 C29 1.5027(15) . ?
C24 H24 1.0000 . ?
C24 C35 1.4886(15) . ?
C25 H25 1.0000 . ?
C25 C27 1.5181(18) . ?
C26 H26A 0.9900 . ?
C26 H26B 0.9900 . ?
C29 C30 1.3944(16) . ?
C29 C34 1.3893(17) . ?
C30 H30 0.9500 . ?
C30 C31 1.3925(17) . ?
C31 H31 0.9500 . ?
C31 C32 1.3793(19) . ?
C32 H32 0.9500 . ?
C32 C33 1.3840(19) . ?
C33 H33 0.9500 . ?
C33 C34 1.3900(17) . ?
C34 H34 0.9500 . ?
C35 C36 1.3948(16) . ?
C35 C40 1.3999(15) . ?
C36 H36 0.9500 . ?
C36 C37 1.3844(16) . ?
C37 H37 0.9500 . ?
C37 C38 1.3944(16) . ?
C38 C39 1.3905(16) . ?
C38 C41 1.4840(15) . ?
C39 H39 0.9500 . ?
C39 C40 1.3838(16) . ?
C40 H40 0.9500 . ?
C42 H42A 0.9800 . ?
C42 H42B 0.9800 . ?
C42 H42C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 C4 108.05(8) . . ?
C20 O3 C21 116.50(9) . . ?
C4 N1 H1 110.9(10) . . ?
C4 N1 C5 105.40(9) . . ?
C5 N1 H1 110.5(10) . . ?
O1 C1 C2 115.73(9) . . ?
O1 C1 C3 117.86(9) . . ?
O1 C1 C5 106.59(9) . . ?
C2 C1 C3 61.79(7) . . ?
C2 C1 C5 125.60(9) . . ?
C3 C1 C5 124.07(9) . . ?
C1 C2 C3 59.37(7) . . ?
C1 C2 C7 116.71(9) . . ?
C7 C2 C3 116.45(9) . . ?
C8 C2 C1 121.88(9) . . ?
C8 C2 C3 122.55(9) . . ?
C8 C2 C7 111.15(9) . . ?
C1 C3 C2 58.84(7) . . ?
C1 C3 H3 112.7 . . ?
C2 C3 H3 112.7 . . ?
C14 C3 C1 125.40(9) . . ?
C14 C3 C2 124.16(9) . . ?
C14 C3 H3 112.7 . . ?
O1 C4 H4 110.1 . . ?
O1 C4 C6 106.07(9) . . ?
N1 C4 O1 109.36(9) . . ?
N1 C4 H4 110.1 . . ?
N1 C4 C6 111.16(10) . . ?
C6 C4 H4 110.1 . . ?
N1 C5 C1 103.50(9) . . ?
N1 C5 H5A 111.1 . . ?
N1 C5 H5B 111.1 . . ?
C1 C5 H5A 111.1 . . ?
C1 C5 H5B 111.1 . . ?
H5A C5 H5B 109.0 . . ?
F1 C6 F2 106.75(10) . . ?
F1 C6 F3 107.32(10) . . ?
F1 C6 C4 111.37(10) . . ?
F2 C6 C4 112.29(10) . . ?
F3 C6 F2 107.01(10) . . ?
F3 C6 C4 111.79(10) . . ?
F4 C7 C2 111.30(9) . . ?
F5 C7 F4 106.40(9) . . ?
F5 C7 C2 113.61(9) . . ?
F6 C7 F4 106.40(9) . . ?
F6 C7 F5 106.30(9) . . ?
F6 C7 C2 112.35(9) . . ?
C9 C8 C2 120.22(10) . . ?
C13 C8 C2 120.06(10) . . ?
C13 C8 C9 119.40(10) . . ?
C8 C9 H9 119.9 . . ?
C10 C9 C8 120.15(11) . . ?
C10 C9 H9 119.9 . . ?
C9 C10 H10 120.0 . . ?
C11 C10 C9 119.99(12) . . ?
C11 C10 H10 120.0 . . ?
C10 C11 H11 119.9 . . ?
C10 C11 C12 120.28(11) . . ?
C12 C11 H11 119.9 . . ?
C11 C12 H12 120.0 . . ?
C11 C12 C13 120.01(12) . . ?
C13 C12 H12 120.0 . . ?
C8 C13 H13 119.9 . . ?
C12 C13 C8 120.17(11) . . ?
C12 C13 H13 119.9 . . ?
C15 C14 C3 117.23(9) . . ?
C15 C14 C19 118.19(10) . . ?
C19 C14 C3 124.54(10) . . ?
C14 C15 H15 119.2 . . ?
C16 C15 C14 121.65(10) . . ?
C16 C15 H15 119.2 . . ?
C15 C16 H16 120.1 . . ?
C15 C16 C17 119.77(10) . . ?
C17 C16 H16 120.1 . . ?
C16 C17 C20 122.22(10) . . ?
C18 C17 C16 119.04(10) . . ?
C18 C17 C20 118.71(9) . . ?
C17 C18 H18 119.5 . . ?
C19 C18 C17 121.04(10) . . ?
C19 C18 H18 119.5 . . ?
C14 C19 H19 119.9 . . ?
C18 C19 C14 120.28(10) . . ?
C18 C19 H19 119.9 . . ?
O2 C20 O3 123.62(10) . . ?
O2 C20 C17 124.18(10) . . ?
O3 C20 C17 112.19(9) . . ?
O3 C21 H21A 109.5 . . ?
O3 C21 H21B 109.5 . . ?
O3 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C22 O4 C25 107.85(9) . . ?
C41 O6 C42 115.56(10) . . ?
C25 N2 H2 110.8(11) . . ?
C25 N2 C26 105.32(9) . . ?
C26 N2 H2 107.0(11) . . ?
O4 C22 C23 115.18(9) . . ?
O4 C22 C24 118.73(9) . . ?
O4 C22 C26 105.60(9) . . ?
C23 C22 C24 61.77(7) . . ?
C23 C22 C26 127.63(10) . . ?
C24 C22 C26 123.35(10) . . ?
C22 C23 C24 59.36(7) . . ?
C22 C23 C28 117.50(10) . . ?
C28 C23 C24 115.75(9) . . ?
C29 C23 C22 121.56(9) . . ?
C29 C23 C24 121.63(9) . . ?
C29 C23 C28 111.85(9) . . ?
C22 C24 C23 58.88(7) . . ?
C22 C24 H24 112.7 . . ?
C23 C24 H24 112.7 . . ?
C35 C24 C22 126.21(10) . . ?
C35 C24 C23 123.47(9) . . ?
C35 C24 H24 112.7 . . ?
O4 C25 N2 108.98(10) . . ?
O4 C25 H25 109.9 . . ?
O4 C25 C27 106.06(9) . . ?
N2 C25 H25 109.9 . . ?
N2 C25 C27 111.92(11) . . ?
C27 C25 H25 109.9 . . ?
N2 C26 C22 102.68(9) . . ?
N2 C26 H26A 111.2 . . ?
N2 C26 H26B 111.2 . . ?
C22 C26 H26A 111.2 . . ?
C22 C26 H26B 111.2 . . ?
H26A C26 H26B 109.1 . . ?
F7 C27 F8 107.10(11) . . ?
F7 C27 F9 107.07(11) . . ?
F7 C27 C25 111.98(11) . . ?
F8 C27 C25 112.23(11) . . ?
F9 C27 F8 107.44(11) . . ?
F9 C27 C25 110.75(11) . . ?
F10 C28 C23 111.38(9) . . ?
F11 C28 F10 106.39(10) . . ?
F11 C28 C23 113.55(9) . . ?
F12 C28 F10 106.54(9) . . ?
F12 C28 F11 106.36(10) . . ?
F12 C28 C23 112.15(10) . . ?
C30 C29 C23 120.46(10) . . ?
C34 C29 C23 120.21(10) . . ?
C34 C29 C30 119.15(10) . . ?
C29 C30 H30 119.9 . . ?
C31 C30 C29 120.21(11) . . ?
C31 C30 H30 119.9 . . ?
C30 C31 H31 120.0 . . ?
C32 C31 C30 119.99(12) . . ?
C32 C31 H31 120.0 . . ?
C31 C32 H32 119.8 . . ?
C31 C32 C33 120.32(11) . . ?
C33 C32 H32 119.8 . . ?
C32 C33 H33 120.1 . . ?
C32 C33 C34 119.82(12) . . ?
C34 C33 H33 120.1 . . ?
C29 C34 C33 120.51(11) . . ?
C29 C34 H34 119.7 . . ?
C33 C34 H34 119.7 . . ?
C36 C35 C24 117.54(9) . . ?
C36 C35 C40 118.32(10) . . ?
C40 C35 C24 124.12(10) . . ?
C35 C36 H36 119.1 . . ?
C37 C36 C35 121.71(10) . . ?
C37 C36 H36 119.1 . . ?
C36 C37 H37 120.3 . . ?
C36 C37 C38 119.43(11) . . ?
C38 C37 H37 120.3 . . ?
C37 C38 C41 122.21(10) . . ?
C39 C38 C37 119.34(10) . . ?
C39 C38 C41 118.44(10) . . ?
C38 C39 H39 119.5 . . ?
C40 C39 C38 121.04(10) . . ?
C40 C39 H39 119.5 . . ?
C35 C40 H40 120.0 . . ?
C39 C40 C35 120.10(11) . . ?
C39 C40 H40 120.0 . . ?
O5 C41 O6 123.39(11) . . ?
O5 C41 C38 124.02(11) . . ?
O6 C41 C38 112.58(9) . . ?
O6 C42 H42A 109.5 . . ?
O6 C42 H42B 109.5 . . ?
O6 C42 H42C 109.5 . . ?
H42A C42 H42B 109.5 . . ?
H42A C42 H42C 109.5 . . ?
H42B C42 H42C 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 C1 C2 C3 109.28(10) . . . . ?
O1 C1 C2 C7 -144.36(10) . . . . ?
O1 C1 C2 C8 -2.32(14) . . . . ?
O1 C1 C3 C2 -105.88(10) . . . . ?
O1 C1 C3 C14 6.16(15) . . . . ?
O1 C1 C5 N1 -22.40(11) . . . . ?
O1 C4 C6 F1 -176.19(9) . . . . ?
O1 C4 C6 F2 64.14(12) . . . . ?
O1 C4 C6 F3 -56.14(12) . . . . ?
N1 C4 C6 F1 65.03(12) . . . . ?
N1 C4 C6 F2 -54.64(12) . . . . ?
N1 C4 C6 F3 -174.92(9) . . . . ?
C1 O1 C4 N1 7.70(12) . . . . ?
C1 O1 C4 C6 -112.26(10) . . . . ?
C1 C2 C3 C14 -114.07(12) . . . . ?
C1 C2 C7 F4 77.38(12) . . . . ?
C1 C2 C7 F5 -42.70(14) . . . . ?
C1 C2 C7 F6 -163.42(9) . . . . ?
C1 C2 C8 C9 -56.26(14) . . . . ?
C1 C2 C8 C13 130.31(11) . . . . ?
C1 C3 C14 C15 158.17(10) . . . . ?
C1 C3 C14 C19 -19.55(17) . . . . ?
C2 C1 C3 C14 112.04(11) . . . . ?
C2 C1 C5 N1 -162.77(10) . . . . ?
C2 C3 C14 C15 -128.38(11) . . . . ?
C2 C3 C14 C19 53.90(16) . . . . ?
C2 C8 C9 C10 -172.75(10) . . . . ?
C2 C8 C13 C12 172.50(10) . . . . ?
C3 C1 C2 C7 106.36(10) . . . . ?
C3 C1 C2 C8 -111.60(11) . . . . ?
C3 C1 C5 N1 119.80(11) . . . . ?
C3 C2 C7 F4 144.63(10) . . . . ?
C3 C2 C7 F5 24.55(14) . . . . ?
C3 C2 C7 F6 -96.17(11) . . . . ?
C3 C2 C8 C9 -127.91(11) . . . . ?
C3 C2 C8 C13 58.66(14) . . . . ?
C3 C14 C15 C16 -175.98(10) . . . . ?
C3 C14 C19 C18 176.66(10) . . . . ?
C4 O1 C1 C2 154.30(9) . . . . ?
C4 O1 C1 C3 -135.51(10) . . . . ?
C4 O1 C1 C5 9.44(11) . . . . ?
C4 N1 C5 C1 26.59(12) . . . . ?
C5 N1 C4 O1 -22.13(13) . . . . ?
C5 N1 C4 C6 94.66(11) . . . . ?
C5 C1 C2 C3 -113.44(12) . . . . ?
C5 C1 C2 C7 -7.08(16) . . . . ?
C5 C1 C2 C8 134.96(11) . . . . ?
C5 C1 C3 C2 115.76(12) . . . . ?
C5 C1 C3 C14 -132.20(11) . . . . ?
C7 C2 C3 C1 -106.78(11) . . . . ?
C7 C2 C3 C14 139.15(11) . . . . ?
C7 C2 C8 C9 87.64(12) . . . . ?
C7 C2 C8 C13 -85.79(12) . . . . ?
C8 C2 C3 C1 110.50(11) . . . . ?
C8 C2 C3 C14 -3.57(16) . . . . ?
C8 C2 C7 F4 -68.57(12) . . . . ?
C8 C2 C7 F5 171.36(9) . . . . ?
C8 C2 C7 F6 50.64(12) . . . . ?
C8 C9 C10 C11 0.18(17) . . . . ?
C9 C8 C13 C12 -0.98(16) . . . . ?
C9 C10 C11 C12 -0.84(18) . . . . ?
C10 C11 C12 C13 0.58(18) . . . . ?
C11 C12 C13 C8 0.34(18) . . . . ?
C13 C8 C9 C10 0.73(16) . . . . ?
C14 C15 C16 C17 -0.92(17) . . . . ?
C15 C14 C19 C18 -1.04(16) . . . . ?
C15 C16 C17 C18 -0.92(16) . . . . ?
C15 C16 C17 C20 177.14(10) . . . . ?
C16 C17 C18 C19 1.77(16) . . . . ?
C16 C17 C20 O2 -179.83(11) . . . . ?
C16 C17 C20 O3 -0.53(15) . . . . ?
C17 C18 C19 C14 -0.78(17) . . . . ?
C18 C17 C20 O2 -1.76(16) . . . . ?
C18 C17 C20 O3 177.54(10) . . . . ?
C19 C14 C15 C16 1.89(16) . . . . ?
C20 C17 C18 C19 -176.37(10) . . . . ?
C21 O3 C20 O2 2.19(16) . . . . ?
C21 O3 C20 C17 -177.11(10) . . . . ?
O4 C22 C23 C24 -110.51(11) . . . . ?
O4 C22 C23 C28 144.37(10) . . . . ?
O4 C22 C23 C29 0.07(15) . . . . ?
O4 C22 C24 C23 104.86(11) . . . . ?
O4 C22 C24 C35 -6.02(16) . . . . ?
O4 C22 C26 N2 29.98(11) . . . . ?
O4 C25 C27 F7 52.01(13) . . . . ?
O4 C25 C27 F8 -68.48(13) . . . . ?
O4 C25 C27 F9 171.45(10) . . . . ?
N2 C25 C27 F7 170.75(10) . . . . ?
N2 C25 C27 F8 50.25(14) . . . . ?
N2 C25 C27 F9 -69.82(14) . . . . ?
C22 O4 C25 N2 1.00(12) . . . . ?
C22 O4 C25 C27 121.66(10) . . . . ?
C22 C23 C24 C35 115.34(12) . . . . ?
C22 C23 C28 F10 -83.33(12) . . . . ?
C22 C23 C28 F11 36.75(14) . . . . ?
C22 C23 C28 F12 157.36(10) . . . . ?
C22 C23 C29 C30 52.89(15) . . . . ?
C22 C23 C29 C34 -132.05(11) . . . . ?
C22 C24 C35 C36 -160.77(10) . . . . ?
C22 C24 C35 C40 17.94(17) . . . . ?
C23 C22 C24 C35 -110.88(12) . . . . ?
C23 C22 C26 N2 170.60(11) . . . . ?
C23 C24 C35 C36 125.72(11) . . . . ?
C23 C24 C35 C40 -55.57(16) . . . . ?
C23 C29 C30 C31 174.73(10) . . . . ?
C23 C29 C34 C33 -174.43(10) . . . . ?
C24 C22 C23 C28 -105.12(11) . . . . ?
C24 C22 C23 C29 110.58(11) . . . . ?
C24 C22 C26 N2 -111.38(12) . . . . ?
C24 C23 C28 F10 -150.57(10) . . . . ?
C24 C23 C28 F11 -30.49(14) . . . . ?
C24 C23 C28 F12 90.12(12) . . . . ?
C24 C23 C29 C30 123.97(12) . . . . ?
C24 C23 C29 C34 -60.96(14) . . . . ?
C24 C35 C36 C37 176.25(10) . . . . ?
C24 C35 C40 C39 -177.33(10) . . . . ?
C25 O4 C22 C23 -165.67(9) . . . . ?
C25 O4 C22 C24 124.11(10) . . . . ?
C25 O4 C22 C26 -19.40(11) . . . . ?
C25 N2 C26 C22 -28.99(12) . . . . ?
C26 N2 C25 O4 18.41(13) . . . . ?
C26 N2 C25 C27 -98.58(11) . . . . ?
C26 C22 C23 C24 111.96(13) . . . . ?
C26 C22 C23 C28 6.84(17) . . . . ?
C26 C22 C23 C29 -137.46(12) . . . . ?
C26 C22 C24 C23 -118.44(12) . . . . ?
C26 C22 C24 C35 130.68(12) . . . . ?
C28 C23 C24 C22 108.06(11) . . . . ?
C28 C23 C24 C35 -136.59(11) . . . . ?
C28 C23 C29 C30 -93.22(12) . . . . ?
C28 C23 C29 C34 81.85(13) . . . . ?
C29 C23 C24 C22 -110.47(11) . . . . ?
C29 C23 C24 C35 4.88(16) . . . . ?
C29 C23 C28 F10 64.28(13) . . . . ?
C29 C23 C28 F11 -175.64(10) . . . . ?
C29 C23 C28 F12 -55.03(13) . . . . ?
C29 C30 C31 C32 -0.15(17) . . . . ?
C30 C29 C34 C33 0.70(17) . . . . ?
C30 C31 C32 C33 0.39(18) . . . . ?
C31 C32 C33 C34 -0.08(19) . . . . ?
C32 C33 C34 C29 -0.47(18) . . . . ?
C34 C29 C30 C31 -0.38(16) . . . . ?
C35 C36 C37 C38 1.40(16) . . . . ?
C36 C35 C40 C39 1.38(17) . . . . ?
C36 C37 C38 C39 0.93(16) . . . . ?
C36 C37 C38 C41 -177.86(10) . . . . ?
C37 C38 C39 C40 -2.08(17) . . . . ?
C37 C38 C41 O5 -171.55(11) . . . . ?
C37 C38 C41 O6 9.51(15) . . . . ?
C38 C39 C40 C35 0.91(18) . . . . ?
C39 C38 C41 O5 9.65(17) . . . . ?
C39 C38 C41 O6 -169.28(10) . . . . ?
C40 C35 C36 C37 -2.54(16) . . . . ?
C41 C38 C39 C40 176.75(10) . . . . ?
C42 O6 C41 O5 -2.19(16) . . . . ?
C42 O6 C41 C38 176.75(10) . . . . ?

_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
- Detector area scaling
- B-factor correction
;
_oxdiff_exptl_absorpt_empirical_full_max 1.302
_oxdiff_exptl_absorpt_empirical_full_min 0.720
