# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# 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_202107195
_database_code_depnum_ccdc_archive 'CCDC 2285183'
loop_
_audit_author_name
_audit_author_address
zhanglinghong
;Henan normal university
China
;
_audit_update_record             
;
2023-07-28 deposited with the CCDC.	2024-05-07 downloaded from the CCDC.
;
_audit_creation_date             2021-07-06
_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         'C16 H10 Br F3 O'
_chemical_formula_sum            'C16 H10 Br F3 O'
_chemical_formula_weight         355.15
_chemical_melting_point          ?
_chemical_oxdiff_formula         C16H10O1F3Br1
_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'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   16.291(2)
_cell_length_b                   6.2878(6)
_cell_length_c                   15.4937(18)
_cell_angle_alpha                90
_cell_angle_beta                 116.475(15)
_cell_angle_gamma                90
_cell_volume                     1420.7(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1307
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      65.1470
_cell_measurement_theta_min      5.6920
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    4.235
_exptl_absorpt_correction_T_max  0.756
_exptl_absorpt_correction_T_min  0.444
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
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    1.660
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             704
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 -3 -5 0.0720
0 -3 5 0.1390
0 -1 9 0.1307
0 2 -7 0.1331
-10 1 2 0.0433
10 -1 -2 0.0338
3 3 5 0.0372
-9 -1 -2 0.0566
1 0 -9 0.1234

_exptl_crystal_size_max          0.339
_exptl_crystal_size_mid          0.137
_exptl_crystal_size_min          0.078
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
0.1521 -3.3513 -5.1864 0.2323 0.9676 0.0986
0.3574 -3.4691 4.5957 0.0716 0.2969 0.9522
0.2341 -0.7687 8.7370 -0.1149 -0.4802 0.8696
-0.3206 2.2624 -7.3570 0.0272 0.1148 -0.9930
-9.9393 0.8640 1.8076 0.9024 -0.2167 -0.3724
9.9104 -0.8838 -1.7446 -0.8995 0.2160 0.3797
3.1700 2.6038 5.0347 -0.5175 -0.8447 0.1369
-8.9848 -1.0003 -2.0031 0.9603 0.3811 -0.3618
0.9891 -0.0003 -8.9902 0.0378 0.6282 -0.7214

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0355
_diffrn_reflns_av_unetI/netI     0.0445
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            5416
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.062
_diffrn_reflns_theta_max         67.062
_diffrn_reflns_theta_min         5.714
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2312
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -108.00 -32.00   1.00    1.00    --  -33.50 178.00-180.00   76
  2  ω   -102.00 -37.00   1.00    1.00    --  -33.50 -57.00-120.00   65
  3  ω    -87.00 -32.00   1.00    1.00    --  -33.50 178.00 -90.00   55
  4  ω    -96.00 -65.00   1.00    1.00    --  -33.50 -57.00   0.00   31
  5  ω     63.00 107.00   1.00    1.00    --   36.54 178.00  30.00   44
  6  ω     57.00 111.00   1.00    1.00    --   36.54 178.00-180.00   54
  7  ω     20.00  64.00   1.00    1.00    --   36.54 -77.00   0.00   44
  8  ω    -21.00   8.00   1.00    1.00    --   36.54 -77.00   0.00   29
  9  ω     77.00 106.00   1.00    1.00    --   36.54  37.00-120.00   29
 10  ω     60.00  97.00   1.00    1.00    --   36.54 178.00 -60.00   37
 11  ω     15.00  49.00   1.00    1.00    --   36.54  37.00-120.00   34
 12  ω    -10.00  35.00   1.00    1.00    --   36.54 -57.00   0.00   45
 13  ω     38.00  81.00   1.00    6.50    --  108.00 -94.00 150.00   43
 14  ω     80.00 134.00   1.00    6.50    --  108.00 -30.00 120.00   54
 15  ω    152.00 177.00   1.00    6.50    --  108.00  77.00 -30.00   25
 16  ω     83.00 144.00   1.00    6.50    --  108.00  77.00 -30.00   61
 17  ω     43.00  70.00   1.00    6.50    --  108.00 -30.00 120.00   27
 18  ω     58.00  85.00   1.00    6.50    --  108.00 -94.00-150.00   27
 19  ω     68.00 120.00   1.00    6.50    --  108.00 178.00 150.00   52
 20  ω     95.00 169.00   1.00    6.50    --  108.00  61.00 -90.00   74
 21  ω     65.00  98.00   1.00    6.50    --  108.00 -94.00  30.00   33
 22  ω     41.00 126.00   1.00    6.50    --  108.00 -61.00-150.00   85
;
_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      -0.0979129000
_diffrn_orient_matrix_UB_12      -0.0505658000
_diffrn_orient_matrix_UB_13      -0.0149782000
_diffrn_orient_matrix_UB_21      -0.0066630000
_diffrn_orient_matrix_UB_22      -0.1797837000
_diffrn_orient_matrix_UB_23      -0.0705990000
_diffrn_orient_matrix_UB_31      0.0390649000
_diffrn_orient_matrix_UB_32      -0.1584690000
_diffrn_orient_matrix_UB_33      0.0845420000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1784
_reflns_number_total             2534
_reflns_odcompleteness_completeness 99.86
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         1.104
_refine_diff_density_min         -0.343
_refine_diff_density_rms         0.073
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.968
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         2534
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0775
_refine_ls_R_factor_gt           0.0560
_refine_ls_restrained_S_all      0.969
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0994P)²+0.2603P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1486
_refine_ls_wR_factor_ref         0.1743
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Restrained distances
 Br1A-C3A
 1.9 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C4) = Uanis(C4A)
Uanis(C5) = Uanis(C5A)
Uanis(C2) = Uanis(C2A)
Uanis(C1) = Uanis(C1A)
Uanis(C3) = Uanis(C3A)
Uanis(C6) = Uanis(C6A)
Uanis(Br1) = Uanis(Br1A)
4. Others
 Sof(Br1A)=Sof(C3A)=Sof(C4A)=Sof(H4A)=Sof(C5A)=Sof(H5A)=Sof(C6A)=Sof(C1A)=
 Sof(H1A)=Sof(C2A)=Sof(H2A)=1-FVAR(1)
 Sof(Br1)=Sof(C1)=Sof(H1)=Sof(C2)=Sof(H2)=Sof(C3)=Sof(C4)=Sof(H4)=Sof(C5)=
 Sof(H5)=Sof(C6)=FVAR(1)
5.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C4A(H4A), C5A(H5A), C1A(H1A), C2A(H2A), C4(H4), C5(H5),
 C8(H8), C11(H11), C12(H12), C13(H13), C14(H14), C15(H15)
5.b Fitted hexagon refined as free rotating group:
 C3A(C4A,C5A,C6A,C1A,C2A)
;
_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
Br1 Br 0.9673(3) 1.1366(6) 1.1719(3) 0.0973(7) Uani 0.755(15) 1 d . . P A 1
Br1A Br 0.9772(8) 1.123(2) 1.1574(8) 0.0973(7) Uani 0.245(15) 1 d D . P A 2
F1 F 0.5949(2) 0.1950(6) 0.7937(2) 0.0887(9) Uani 1 1 d . . . . .
F2 F 0.49315(19) 0.3334(5) 0.6639(2) 0.0832(9) Uani 1 1 d . . . . .
F3 F 0.5587(2) 0.0454(5) 0.6583(2) 0.0795(8) Uani 1 1 d . . . . .
O1 O 0.7973(2) 0.3621(5) 0.8211(2) 0.0635(8) Uani 1 1 d . . . . .
C1 C 0.7690(6) 0.872(2) 0.9247(11) 0.070(2) Uani 0.755(15) 1 d . . P A 1
H1 H 0.7111 0.9151 0.8792 0.084 Uiso 0.755(15) 1 calc R . P A 1
C2 C 0.8178(7) 1.002(2) 1.0016(11) 0.071(2) Uani 0.755(15) 1 d . . P A 1
H2 H 0.7931 1.1314 1.0080 0.085 Uiso 0.755(15) 1 calc R . P A 1
C3 C 0.9030(7) 0.9418(15) 1.0689(6) 0.068(2) Uani 0.755(15) 1 d . . P A 1
C3A C 0.900(2) 0.970(5) 1.051(2) 0.068(2) Uani 0.245(15) 1 d D . P A 2
C4A C 0.9483(13) 0.817(4) 1.0274(16) 0.084(3) Uani 0.245(15) 1 d G . P A 2
H4A H 1.0118 0.8092 1.0621 0.100 Uiso 0.245(15) 1 calc R . P A 2
C5A C 0.9017(17) 0.677(4) 0.9519(16) 0.071(2) Uani 0.245(15) 1 d G . P A 2
H5A H 0.9340 0.5750 0.9360 0.086 Uiso 0.245(15) 1 calc R . P A 2
C6A C 0.8069(17) 0.689(5) 0.900(2) 0.0564(18) Uani 0.245(15) 1 d G . P A 2
C1A C 0.7586(13) 0.842(8) 0.924(3) 0.070(2) Uani 0.245(15) 1 d G . P A 2
H1A H 0.6951 0.8501 0.8891 0.084 Uiso 0.245(15) 1 calc R . P A 2
C2A C 0.8052(19) 0.982(7) 0.999(3) 0.071(2) Uani 0.245(15) 1 d G . P A 2
H2A H 0.7728 1.0843 1.0152 0.085 Uiso 0.245(15) 1 calc R . P A 2
C4 C 0.9392(5) 0.7502(16) 1.0608(6) 0.084(3) Uani 0.755(15) 1 d . . P A 1
H4 H 0.9967 0.7086 1.1075 0.100 Uiso 0.755(15) 1 calc R . P A 1
C5 C 0.8900(5) 0.6189(13) 0.9830(6) 0.071(2) Uani 0.755(15) 1 d . . P A 1
H5 H 0.9149 0.4895 0.9776 0.086 Uiso 0.755(15) 1 calc R . P A 1
C6 C 0.8037(6) 0.6779(17) 0.9129(7) 0.0564(18) Uani 0.755(15) 1 d . . P A 1
C7 C 0.7519(3) 0.5442(7) 0.8274(3) 0.0574(9) Uani 1 1 d . . . . .
C8 C 0.6674(3) 0.5581(7) 0.7550(3) 0.0602(10) Uani 1 1 d . . . . .
H8 H 0.6269 0.6700 0.7456 0.072 Uiso 1 1 calc R . . . .
C9 C 0.6475(3) 0.3663(7) 0.6914(3) 0.0549(9) Uani 1 1 d . . . . .
C10 C 0.7405(3) 0.2575(7) 0.7363(3) 0.0553(9) Uani 1 1 d . . . . .
C11 C 0.7722(3) 0.0940(8) 0.7057(3) 0.0673(11) Uani 1 1 d . . . . .
H11 H 0.8300 0.0427 0.7474 0.081 Uiso 1 1 calc R . . . .
C12 C 0.7257(4) -0.0101(10) 0.6143(4) 0.0778(13) Uani 1 1 d . . . . .
H12 H 0.7436 -0.1488 0.6105 0.093 Uiso 1 1 calc R . . . .
C13 C 0.6584(4) 0.0726(10) 0.5332(4) 0.0804(14) Uani 1 1 d . . . . .
H13 H 0.6338 -0.0164 0.4797 0.096 Uiso 1 1 calc R . . . .
C14 C 0.6210(4) 0.2833(10) 0.5207(3) 0.0769(13) Uani 1 1 d . . . . .
H14 H 0.5946 0.3337 0.4577 0.092 Uiso 1 1 calc R . . . .
C15 C 0.6185(3) 0.4171(8) 0.5861(3) 0.0673(11) Uani 1 1 d . . . . .
H15 H 0.5971 0.5539 0.5653 0.081 Uiso 1 1 calc R . . . .
C16 C 0.5741(3) 0.2341(7) 0.7020(3) 0.0606(10) Uani 1 1 d . . . . .


_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
Br1 C3 1.911(8) . ?
Br1A C3A 1.838(18) . ?
F1 C16 1.327(5) . ?
F2 C16 1.335(5) . ?
F3 C16 1.333(6) . ?
O1 C7 1.390(5) . ?
O1 C10 1.389(5) . ?
C1 H1 0.9300 . ?
C1 C2 1.369(9) . ?
C1 C6 1.393(9) . ?
C2 H2 0.9300 . ?
C2 C3 1.367(10) . ?
C3 C4 1.371(10) . ?
C3A C4A 1.3900 . ?
C3A C2A 1.3900 . ?
C4A H4A 0.9300 . ?
C4A C5A 1.3900 . ?
C5A H5A 0.9300 . ?
C5A C6A 1.3900 . ?
C6A C1A 1.3900 . ?
C6A C7 1.415(17) . ?
C1A H1A 0.9300 . ?
C1A C2A 1.3900 . ?
C2A H2A 0.9300 . ?
C4 H4 0.9300 . ?
C4 C5 1.384(10) . ?
C5 H5 0.9300 . ?
C5 C6 1.390(10) . ?
C6 C7 1.475(9) . ?
C7 C8 1.336(6) . ?
C8 H8 0.9300 . ?
C8 C9 1.499(6) . ?
C9 C10 1.519(6) . ?
C9 C15 1.516(6) . ?
C9 C16 1.526(6) . ?
C10 C11 1.330(6) . ?
C11 H11 0.9300 . ?
C11 C12 1.431(7) . ?
C12 H12 0.9300 . ?
C12 C13 1.350(8) . ?
C13 H13 0.9300 . ?
C13 C14 1.435(8) . ?
C14 H14 0.9300 . ?
C14 C15 1.331(7) . ?
C15 H15 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
C10 O1 C7 107.8(3) . . ?
C2 C1 H1 119.1 . . ?
C2 C1 C6 121.7(6) . . ?
C6 C1 H1 119.1 . . ?
C1 C2 H2 120.1 . . ?
C3 C2 C1 119.7(6) . . ?
C3 C2 H2 120.1 . . ?
C2 C3 Br1 116.8(7) . . ?
C2 C3 C4 120.5(6) . . ?
C4 C3 Br1 122.8(7) . . ?
C4A C3A Br1A 111.0(16) . . ?
C4A C3A C2A 120.0 . . ?
C2A C3A Br1A 129.0(16) . . ?
C3A C4A H4A 120.0 . . ?
C3A C4A C5A 120.0 . . ?
C5A C4A H4A 120.0 . . ?
C4A C5A H5A 120.0 . . ?
C4A C5A C6A 120.0 . . ?
C6A C5A H5A 120.0 . . ?
C5A C6A C7 125(2) . . ?
C1A C6A C5A 120.0 . . ?
C1A C6A C7 115(2) . . ?
C6A C1A H1A 120.0 . . ?
C6A C1A C2A 120.0 . . ?
C2A C1A H1A 120.0 . . ?
C3A C2A H2A 120.0 . . ?
C1A C2A C3A 120.0 . . ?
C1A C2A H2A 120.0 . . ?
C3 C4 H4 120.1 . . ?
C3 C4 C5 119.8(6) . . ?
C5 C4 H4 120.1 . . ?
C4 C5 H5 119.6 . . ?
C4 C5 C6 120.9(6) . . ?
C6 C5 H5 119.6 . . ?
C1 C6 C7 121.0(7) . . ?
C5 C6 C1 117.4(6) . . ?
C5 C6 C7 121.6(8) . . ?
O1 C7 C6A 114.8(13) . . ?
O1 C7 C6 115.1(5) . . ?
C8 C7 O1 112.1(4) . . ?
C8 C7 C6A 132.5(13) . . ?
C8 C7 C6 132.8(5) . . ?
C7 C8 H8 125.1 . . ?
C7 C8 C9 109.8(4) . . ?
C9 C8 H8 125.1 . . ?
C8 C9 C10 100.5(3) . . ?
C8 C9 C15 114.3(4) . . ?
C8 C9 C16 108.5(4) . . ?
C10 C9 C16 112.0(3) . . ?
C15 C9 C10 110.9(4) . . ?
C15 C9 C16 110.4(4) . . ?
O1 C10 C9 109.2(3) . . ?
C11 C10 O1 120.2(4) . . ?
C11 C10 C9 130.6(4) . . ?
C10 C11 H11 117.0 . . ?
C10 C11 C12 126.0(4) . . ?
C12 C11 H11 117.0 . . ?
C11 C12 H12 116.7 . . ?
C13 C12 C11 126.6(5) . . ?
C13 C12 H12 116.7 . . ?
C12 C13 H13 116.5 . . ?
C12 C13 C14 126.9(5) . . ?
C14 C13 H13 116.5 . . ?
C13 C14 H14 115.2 . . ?
C15 C14 C13 129.5(5) . . ?
C15 C14 H14 115.2 . . ?
C9 C15 H15 117.1 . . ?
C14 C15 C9 125.8(5) . . ?
C14 C15 H15 117.1 . . ?
F1 C16 F2 106.9(4) . . ?
F1 C16 F3 106.2(4) . . ?
F1 C16 C9 112.2(4) . . ?
F2 C16 C9 111.4(4) . . ?
F3 C16 F2 105.5(4) . . ?
F3 C16 C9 114.1(4) . . ?

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
Br1 C3 C4 C5 -178.3(7) . . . . ?
Br1A C3A C4A C5A 177(2) . . . . ?
Br1A C3A C2A C1A -176(3) . . . . ?
O1 C7 C8 C9 1.8(5) . . . . ?
O1 C10 C11 C12 -171.5(5) . . . . ?
C1 C2 C3 Br1 178.5(9) . . . . ?
C1 C2 C3 C4 -1.2(13) . . . . ?
C1 C6 C7 O1 175.5(7) . . . . ?
C1 C6 C7 C8 -7.5(12) . . . . ?
C2 C1 C6 C5 0.7(11) . . . . ?
C2 C1 C6 C7 -177.3(10) . . . . ?
C2 C3 C4 C5 1.3(15) . . . . ?
C3 C4 C5 C6 -0.4(15) . . . . ?
C3A C4A C5A C6A 0.0 . . . . ?
C4A C3A C2A C1A 0.0 . . . . ?
C4A C5A C6A C1A 0.0 . . . . ?
C4A C5A C6A C7 -174(3) . . . . ?
C5A C6A C1A C2A 0.0 . . . . ?
C5A C6A C7 O1 11(4) . . . . ?
C5A C6A C7 C8 -159.7(19) . . . . ?
C6A C1A C2A C3A 0.0 . . . . ?
C6A C7 C8 C9 172(2) . . . . ?
C1A C6A C7 O1 -164.1(17) . . . . ?
C1A C6A C7 C8 26(3) . . . . ?
C2A C3A C4A C5A 0.0 . . . . ?
C4 C5 C6 C1 -0.5(12) . . . . ?
C4 C5 C6 C7 177.4(7) . . . . ?
C5 C6 C7 O1 -2.4(12) . . . . ?
C5 C6 C7 C8 174.7(8) . . . . ?
C6 C1 C2 C3 0.2(12) . . . . ?
C6 C7 C8 C9 -175.3(7) . . . . ?
C7 O1 C10 C9 -7.4(5) . . . . ?
C7 O1 C10 C11 170.5(4) . . . . ?
C7 C6A C1A C2A 175(3) . . . . ?
C7 C8 C9 C10 -5.8(5) . . . . ?
C7 C8 C9 C15 -124.6(4) . . . . ?
C7 C8 C9 C16 111.8(4) . . . . ?
C8 C9 C10 O1 8.0(4) . . . . ?
C8 C9 C10 C11 -169.7(5) . . . . ?
C8 C9 C15 C14 160.7(5) . . . . ?
C8 C9 C16 F1 -51.1(5) . . . . ?
C8 C9 C16 F2 68.8(4) . . . . ?
C8 C9 C16 F3 -171.9(3) . . . . ?
C9 C10 C11 C12 5.9(9) . . . . ?
C10 O1 C7 C6A -168.7(19) . . . . ?
C10 O1 C7 C6 -178.7(6) . . . . ?
C10 O1 C7 C8 3.6(5) . . . . ?
C10 C9 C15 C14 48.0(6) . . . . ?
C10 C9 C16 F1 58.9(5) . . . . ?
C10 C9 C16 F2 178.8(4) . . . . ?
C10 C9 C16 F3 -61.9(5) . . . . ?
C10 C11 C12 C13 22.8(9) . . . . ?
C11 C12 C13 C14 1.5(10) . . . . ?
C12 C13 C14 C15 -24.7(10) . . . . ?
C13 C14 C15 C9 -6.8(9) . . . . ?
C15 C9 C10 O1 129.2(4) . . . . ?
C15 C9 C10 C11 -48.5(7) . . . . ?
C15 C9 C16 F1 -176.9(4) . . . . ?
C15 C9 C16 F2 -57.1(5) . . . . ?
C15 C9 C16 F3 62.2(5) . . . . ?
C16 C9 C10 O1 -107.0(4) . . . . ?
C16 C9 C10 C11 75.3(6) . . . . ?
C16 C9 C15 C14 -76.7(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 1.263
_oxdiff_exptl_absorpt_empirical_full_min 0.873
####################################################################### 
# 
# 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_zhlh202308_auto
_database_code_depnum_ccdc_archive 'CCDC 2286090'
loop_
_audit_author_name
_audit_author_address
zhanglinghong
;Henan normal university
China
;
_audit_update_record             
;
2023-08-02 deposited with the CCDC.	2024-05-07 downloaded from the CCDC.
;
_audit_creation_date             2023-08-01
_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         'C28 H31 F3 O'
_chemical_formula_sum            'C28 H31 F3 O'
_chemical_formula_weight         440.53
_chemical_melting_point          ?
_chemical_oxdiff_formula         C20H20N4O4F3
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'
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      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                   9.1987(6)
_cell_length_b                   11.0072(6)
_cell_length_c                   12.2093(6)
_cell_angle_alpha                90.074(4)
_cell_angle_beta                 92.871(4)
_cell_angle_gamma                96.049(5)
_cell_volume                     1227.76(12)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3615
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.0840
_cell_measurement_theta_min      4.0220
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.706
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.75102
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.81a (Rigaku Oxford Diffraction, 2023)
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    1.192
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             468
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0295
_diffrn_reflns_av_unetI/netI     0.0382
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            8391
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.069
_diffrn_reflns_theta_max         67.069
_diffrn_reflns_theta_min         3.625
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2312
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -104.00 -11.00   1.00    1.00    --  -33.50 -37.00  90.00   93
  2  ω    -71.00  39.00   1.00    1.00    --  -33.50  19.00  30.00  110
  3  ω    -62.00  36.00   1.00    1.00    --  -33.50  77.00  60.00   98
  4  ω   -108.00 -35.00   1.00    1.00    --  -33.50 178.00 -30.00   73
  5  ω   -102.00 -15.00   1.00    1.00    --  -33.50 -57.00-150.00   87
  6  ω   -108.00 -35.00   1.00    1.00    --  -33.50 178.00-180.00   73
  7  ω      1.00  76.00   1.00    1.00    --   36.47 -99.00-180.00   75
  8  ω      1.00  76.00   1.00    1.00    --   36.47 -99.00 -30.00   75
  9  ω     38.00 128.00   1.00    5.00    --  108.00 -45.00  60.00   90
 10  ω     38.00 107.00   1.00    5.00    --  108.00 -94.00   0.00   69
 11  ω    101.00 177.00   1.00    5.00    --  108.00  77.00   0.00   76
 12  ω     71.00 107.00   1.00    5.00    --  108.00 -94.00  90.00   36
 13  ω     41.00 105.00   1.00    5.00    --  108.00 -94.00-150.00   64
 14  ω     63.00 126.00   1.00    5.00    --  108.00 -61.00 -30.00   63
 15  ω     42.00 128.00   1.00    5.00    --  108.00 -45.00-120.00   86
 16  ω    126.00 166.00   1.00    5.00    --  108.00 111.00  30.00   40
 17  ω     89.00 170.00   1.00    5.00    --  108.00  45.00  60.00   81
 18  ω    105.00 157.00   1.00    5.00    --  108.00  61.00-180.00   52
 19  ω     65.00  91.00   1.00    5.00    --  108.00 178.00-180.00   26
 20  ω     75.00 105.00   1.00    5.00    --  108.00 -94.00  30.00   30
 21  ω     64.00 109.00   1.00    5.00    --  108.00-111.00 -30.00   45
 22  ω     68.00 105.00   1.00    5.00    --  108.00 -94.00 150.00   37
 23  ω     72.00 177.00   1.00    5.00    --  108.00   0.00 -30.00  105
;
_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      -0.0978974000
_diffrn_orient_matrix_UB_12      -0.1167849000
_diffrn_orient_matrix_UB_13      0.0285323000
_diffrn_orient_matrix_UB_21      -0.1372199000
_diffrn_orient_matrix_UB_22      0.0634575000
_diffrn_orient_matrix_UB_23      -0.0322972000
_diffrn_orient_matrix_UB_31      0.0047381000
_diffrn_orient_matrix_UB_32      -0.0463040000
_diffrn_orient_matrix_UB_33      -0.1187635000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3413
_reflns_number_total             4357
_reflns_odcompleteness_completeness 99.91
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.81a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.81a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.81a (Rigaku OD, 2023)'
_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    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.671
_refine_diff_density_min         -0.264
_refine_diff_density_rms         0.055
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     295
_refine_ls_number_reflns         4357
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0858
_refine_ls_R_factor_gt           0.0731
_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)+(0.1306P)²+0.3075P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2102
_refine_ls_wR_factor_ref         0.2280
_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:
 C7(H7)
2.b Secondary CH2 refined with riding coordinates:
 C18(H18A,H18B), C19(H19A,H19B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C10(H10), C13(H13), C15(H15)
2.d Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C), C24(H24A,H24B,H24C), C25(H25A,H25B,H25C), C26(H26A,H26B,
 H26C), C27(H27A,H27B,H27C), C28(H28A,H28B,H28C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.6396(4) 0.3806(2) 0.41447(19) 0.1296(11) Uani 1 1 d . . . . .
F2 F 0.8724(4) 0.3850(3) 0.42841(19) 0.1258(10) Uani 1 1 d . . . . .
F3 F 0.7646(4) 0.5040(2) 0.5265(2) 0.1347(12) Uani 1 1 d . . . . .
O1 O 0.66645(19) 0.25304(19) 0.75257(14) 0.0613(5) Uani 1 1 d . . . . .
C1 C 0.6290(4) -0.0166(3) 0.6657(3) 0.0754(8) Uani 1 1 d . . . . .
H1 H 0.5626 0.0156 0.7097 0.090 Uiso 1 1 calc R . . . .
C2 C 0.6628(5) -0.1337(3) 0.6842(3) 0.0883(10) Uani 1 1 d . . . . .
H2 H 0.6202 -0.1791 0.7406 0.106 Uiso 1 1 calc R . . . .
C3 C 0.7577(5) -0.1832(3) 0.6208(3) 0.0889(11) Uani 1 1 d . . . . .
H3 H 0.7794 -0.2629 0.6325 0.107 Uiso 1 1 calc R . . . .
C4 C 0.8214(5) -0.1150(4) 0.5393(3) 0.0947(11) Uani 1 1 d . . . . .
H4 H 0.8871 -0.1486 0.4956 0.114 Uiso 1 1 calc R . . . .
C5 C 0.7894(4) 0.0039(3) 0.5207(3) 0.0778(9) Uani 1 1 d . . . . .
H5 H 0.8347 0.0497 0.4656 0.093 Uiso 1 1 calc R . . . .
C6 C 0.6905(3) 0.0546(2) 0.58390(19) 0.0552(6) Uani 1 1 d . . . . .
C7 C 0.6452(3) 0.1763(3) 0.5589(2) 0.0628(7) Uani 1 1 d . . . . .
H7 H 0.5802 0.1762 0.4928 0.075 Uiso 1 1 calc R . . . .
C8 C 0.6122(3) 0.2675(3) 0.6426(2) 0.0666(8) Uani 1 1 d . . . . .
C9 C 0.7452(4) 0.2964(3) 0.5743(2) 0.0642(7) Uani 1 1 d . . . . .
C10 C 0.8694(3) 0.2954(3) 0.65638(19) 0.0580(6) Uani 1 1 d . . . . .
H10 H 0.9680 0.3102 0.6418 0.070 Uiso 1 1 calc R . . . .
C11 C 0.8169(3) 0.2698(2) 0.75455(19) 0.0513(6) Uani 1 1 d . . . . .
C12 C 0.8916(2) 0.2587(2) 0.86312(17) 0.0457(5) Uani 1 1 d . . . . .
C13 C 0.8238(2) 0.1878(2) 0.94349(18) 0.0449(5) Uani 1 1 d . . . . .
H13 H 0.7316 0.1467 0.9274 0.054 Uiso 1 1 calc R . . . .
C14 C 0.8897(3) 0.1763(2) 1.04764(17) 0.0452(5) Uani 1 1 d . . . . .
C15 C 1.0281(3) 0.2389(2) 1.07042(18) 0.0481(5) Uani 1 1 d . . . . .
H15 H 1.0748 0.2317 1.1391 0.058 Uiso 1 1 calc R . . . .
C16 C 1.0960(2) 0.3115(2) 0.99180(19) 0.0463(5) Uani 1 1 d . . . . .
C17 C 1.0288(2) 0.3221(2) 0.88824(18) 0.0464(5) Uani 1 1 d . . . . .
C18 C 1.1262(3) 0.4127(3) 0.8230(3) 0.0721(8) Uani 1 1 d . . . . .
H18A H 1.0690 0.4701 0.7847 0.086 Uiso 1 1 calc R . . . .
H18B H 1.1786 0.3707 0.7700 0.086 Uiso 1 1 calc R . . . .
C19 C 1.2345(4) 0.4794(3) 0.9117(3) 0.0739(8) Uani 1 1 d . . . . .
H19A H 1.3296 0.5016 0.8824 0.089 Uiso 1 1 calc R . . . .
H19B H 1.1970 0.5528 0.9379 0.089 Uiso 1 1 calc R . . . .
C20 C 1.2447(3) 0.3863(2) 1.0042(2) 0.0558(6) Uani 1 1 d . . . . .
C21 C 0.4713(5) 0.3293(4) 0.6389(3) 0.1077(16) Uani 1 1 d . . . . .
H21A H 0.3966 0.2783 0.6741 0.162 Uiso 1 1 calc GR . . . .
H21B H 0.4401 0.3419 0.5639 0.162 Uiso 1 1 calc GR . . . .
H21C H 0.4885 0.4066 0.6763 0.162 Uiso 1 1 calc GR . . . .
C22 C 0.7547(6) 0.3909(3) 0.4873(3) 0.0916(12) Uani 1 1 d . . . . .
C23 C 0.8105(3) 0.0993(2) 1.13540(19) 0.0514(6) Uani 1 1 d . . . . .
C24 C 0.7786(5) 0.1836(3) 1.2285(3) 0.0896(11) Uani 1 1 d . . . . .
H24A H 0.8690 0.2179 1.2641 0.134 Uiso 1 1 calc GR . . . .
H24B H 0.7205 0.1378 1.2806 0.134 Uiso 1 1 calc GR . . . .
H24C H 0.7260 0.2482 1.1993 0.134 Uiso 1 1 calc GR . . . .
C25 C 0.9029(4) 0.0028(3) 1.1782(3) 0.0845(10) Uani 1 1 d . . . . .
H25A H 0.9257 -0.0475 1.1184 0.127 Uiso 1 1 calc GR . . . .
H25B H 0.8499 -0.0469 1.2306 0.127 Uiso 1 1 calc GR . . . .
H25C H 0.9920 0.0413 1.2129 0.127 Uiso 1 1 calc GR . . . .
C26 C 0.6630(4) 0.0368(4) 1.0899(3) 0.0912(11) Uani 1 1 d . . . . .
H26A H 0.6033 0.0976 1.0624 0.137 Uiso 1 1 calc GR . . . .
H26B H 0.6144 -0.0082 1.1473 0.137 Uiso 1 1 calc GR . . . .
H26C H 0.6789 -0.0180 1.0316 0.137 Uiso 1 1 calc GR . . . .
C27 C 1.3648(3) 0.3032(3) 0.9853(3) 0.0748(8) Uani 1 1 d . . . . .
H27A H 1.3558 0.2359 1.0353 0.112 Uiso 1 1 calc GR . . . .
H27B H 1.4590 0.3488 0.9974 0.112 Uiso 1 1 calc GR . . . .
H27C H 1.3546 0.2727 0.9113 0.112 Uiso 1 1 calc GR . . . .
C28 C 1.2730(3) 0.4471(3) 1.1171(3) 0.0709(8) Uani 1 1 d . . . . .
H28A H 1.1905 0.4890 1.1342 0.106 Uiso 1 1 calc GR . . . .
H28B H 1.3591 0.5044 1.1165 0.106 Uiso 1 1 calc GR . . . .
H28C H 1.2870 0.3858 1.1714 0.106 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C22 1.343(5) . ?
F2 C22 1.337(5) . ?
F3 C22 1.325(4) . ?
O1 C8 1.423(3) . ?
O1 C11 1.376(3) . ?
C1 H1 0.9300 . ?
C1 C2 1.375(5) . ?
C1 C6 1.377(4) . ?
C2 H2 0.9300 . ?
C2 C3 1.351(6) . ?
C3 H3 0.9300 . ?
C3 C4 1.365(6) . ?
C4 H4 0.9300 . ?
C4 C5 1.388(5) . ?
C5 H5 0.9300 . ?
C5 C6 1.382(4) . ?
C6 C7 1.472(4) . ?
C7 H7 0.9800 . ?
C7 C8 1.495(4) . ?
C7 C9 1.534(4) . ?
C8 C9 1.521(5) . ?
C8 C21 1.525(4) . ?
C9 C10 1.483(4) . ?
C9 C22 1.487(5) . ?
C10 H10 0.9300 . ?
C10 C11 1.334(4) . ?
C11 C12 1.473(3) . ?
C12 C13 1.387(3) . ?
C12 C17 1.396(3) . ?
C13 H13 0.9300 . ?
C13 C14 1.393(3) . ?
C14 C15 1.397(3) . ?
C14 C23 1.532(3) . ?
C15 H15 0.9300 . ?
C15 C16 1.381(3) . ?
C16 C17 1.390(3) . ?
C16 C20 1.521(3) . ?
C17 C18 1.522(4) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C18 C19 1.563(5) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C19 C20 1.532(4) . ?
C20 C27 1.532(4) . ?
C20 C28 1.530(4) . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C23 C24 1.526(4) . ?
C23 C25 1.507(4) . ?
C23 C26 1.533(4) . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 0.9600 . ?
C27 H27A 0.9600 . ?
C27 H27B 0.9600 . ?
C27 H27C 0.9600 . ?
C28 H28A 0.9600 . ?
C28 H28B 0.9600 . ?
C28 H28C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C11 O1 C8 108.2(2) . . ?
C2 C1 H1 119.0 . . ?
C2 C1 C6 121.9(3) . . ?
C6 C1 H1 119.0 . . ?
C1 C2 H2 119.8 . . ?
C3 C2 C1 120.3(3) . . ?
C3 C2 H2 119.8 . . ?
C2 C3 H3 120.3 . . ?
C2 C3 C4 119.4(3) . . ?
C4 C3 H3 120.3 . . ?
C3 C4 H4 119.6 . . ?
C3 C4 C5 120.8(4) . . ?
C5 C4 H4 119.6 . . ?
C4 C5 H5 119.9 . . ?
C6 C5 C4 120.2(3) . . ?
C6 C5 H5 119.9 . . ?
C1 C6 C5 117.3(3) . . ?
C1 C6 C7 121.6(3) . . ?
C5 C6 C7 120.9(3) . . ?
C6 C7 H7 112.5 . . ?
C6 C7 C8 124.9(2) . . ?
C6 C7 C9 124.4(2) . . ?
C8 C7 H7 112.5 . . ?
C8 C7 C9 60.2(2) . . ?
C9 C7 H7 112.5 . . ?
O1 C8 C7 117.9(2) . . ?
O1 C8 C9 106.6(2) . . ?
O1 C8 C21 111.2(3) . . ?
C7 C8 C9 61.13(19) . . ?
C7 C8 C21 123.3(2) . . ?
C9 C8 C21 127.9(3) . . ?
C8 C9 C7 58.62(19) . . ?
C10 C9 C7 116.3(2) . . ?
C10 C9 C8 103.0(2) . . ?
C10 C9 C22 118.3(3) . . ?
C22 C9 C7 121.5(2) . . ?
C22 C9 C8 123.8(3) . . ?
C9 C10 H10 125.5 . . ?
C11 C10 C9 108.9(3) . . ?
C11 C10 H10 125.5 . . ?
O1 C11 C12 115.5(2) . . ?
C10 C11 O1 113.2(2) . . ?
C10 C11 C12 131.3(2) . . ?
C13 C12 C11 120.1(2) . . ?
C13 C12 C17 118.9(2) . . ?
C17 C12 C11 121.0(2) . . ?
C12 C13 H13 119.0 . . ?
C12 C13 C14 121.9(2) . . ?
C14 C13 H13 119.0 . . ?
C13 C14 C15 118.2(2) . . ?
C13 C14 C23 120.7(2) . . ?
C15 C14 C23 121.1(2) . . ?
C14 C15 H15 119.7 . . ?
C16 C15 C14 120.5(2) . . ?
C16 C15 H15 119.7 . . ?
C15 C16 C17 120.6(2) . . ?
C15 C16 C20 126.9(2) . . ?
C17 C16 C20 112.6(2) . . ?
C12 C17 C18 131.9(2) . . ?
C16 C17 C12 119.9(2) . . ?
C16 C17 C18 108.1(2) . . ?
C17 C18 H18A 110.9 . . ?
C17 C18 H18B 110.9 . . ?
C17 C18 C19 104.1(2) . . ?
H18A C18 H18B 109.0 . . ?
C19 C18 H18A 110.9 . . ?
C19 C18 H18B 110.9 . . ?
C18 C19 H19A 110.8 . . ?
C18 C19 H19B 110.8 . . ?
H19A C19 H19B 108.9 . . ?
C20 C19 C18 104.6(2) . . ?
C20 C19 H19A 110.8 . . ?
C20 C19 H19B 110.8 . . ?
C16 C20 C19 102.0(2) . . ?
C16 C20 C27 109.2(2) . . ?
C16 C20 C28 112.7(2) . . ?
C19 C20 C27 111.2(3) . . ?
C28 C20 C19 112.5(2) . . ?
C28 C20 C27 109.1(2) . . ?
C8 C21 H21A 109.5 . . ?
C8 C21 H21B 109.5 . . ?
C8 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
F1 C22 C9 113.6(4) . . ?
F2 C22 F1 105.6(3) . . ?
F2 C22 C9 111.7(3) . . ?
F3 C22 F1 106.0(3) . . ?
F3 C22 F2 106.0(4) . . ?
F3 C22 C9 113.2(3) . . ?
C14 C23 C26 111.3(2) . . ?
C24 C23 C14 108.6(2) . . ?
C24 C23 C26 107.1(3) . . ?
C25 C23 C14 110.6(2) . . ?
C25 C23 C24 110.3(3) . . ?
C25 C23 C26 108.8(3) . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C23 C25 H25A 109.5 . . ?
C23 C25 H25B 109.5 . . ?
C23 C25 H25C 109.5 . . ?
H25A C25 H25B 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C23 C26 H26A 109.5 . . ?
C23 C26 H26B 109.5 . . ?
C23 C26 H26C 109.5 . . ?
H26A C26 H26B 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C20 C27 H27A 109.5 . . ?
C20 C27 H27B 109.5 . . ?
C20 C27 H27C 109.5 . . ?
H27A C27 H27B 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C20 C28 H28A 109.5 . . ?
C20 C28 H28B 109.5 . . ?
C20 C28 H28C 109.5 . . ?
H28A C28 H28B 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 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 C8 C9 C7 113.2(2) . . . . ?
O1 C8 C9 C10 0.1(3) . . . . ?
O1 C8 C9 C22 -137.7(3) . . . . ?
O1 C11 C12 C13 26.2(3) . . . . ?
O1 C11 C12 C17 -151.7(2) . . . . ?
C1 C2 C3 C4 1.1(6) . . . . ?
C1 C6 C7 C8 39.8(4) . . . . ?
C1 C6 C7 C9 115.0(3) . . . . ?
C2 C1 C6 C5 -0.5(5) . . . . ?
C2 C1 C6 C7 175.2(3) . . . . ?
C2 C3 C4 C5 -0.3(6) . . . . ?
C3 C4 C5 C6 -0.9(6) . . . . ?
C4 C5 C6 C1 1.2(5) . . . . ?
C4 C5 C6 C7 -174.4(3) . . . . ?
C5 C6 C7 C8 -144.7(3) . . . . ?
C5 C6 C7 C9 -69.5(4) . . . . ?
C6 C1 C2 C3 -0.7(6) . . . . ?
C6 C7 C8 O1 18.9(5) . . . . ?
C6 C7 C8 C9 113.3(3) . . . . ?
C6 C7 C8 C21 -128.2(4) . . . . ?
C6 C7 C9 C8 -114.1(3) . . . . ?
C6 C7 C9 C10 -24.5(4) . . . . ?
C6 C7 C9 C22 133.0(3) . . . . ?
C7 C8 C9 C10 -113.1(2) . . . . ?
C7 C8 C9 C22 109.1(3) . . . . ?
C7 C9 C10 C11 -61.0(3) . . . . ?
C7 C9 C22 F1 20.2(5) . . . . ?
C7 C9 C22 F2 -99.2(4) . . . . ?
C7 C9 C22 F3 141.3(4) . . . . ?
C8 O1 C11 C10 0.6(3) . . . . ?
C8 O1 C11 C12 179.6(2) . . . . ?
C8 C7 C9 C10 89.6(3) . . . . ?
C8 C7 C9 C22 -112.9(4) . . . . ?
C8 C9 C10 C11 0.2(3) . . . . ?
C8 C9 C22 F1 -50.8(4) . . . . ?
C8 C9 C22 F2 -170.2(3) . . . . ?
C8 C9 C22 F3 70.2(5) . . . . ?
C9 C7 C8 O1 -94.4(3) . . . . ?
C9 C7 C8 C21 118.5(4) . . . . ?
C9 C10 C11 O1 -0.5(3) . . . . ?
C9 C10 C11 C12 -179.4(2) . . . . ?
C10 C9 C22 F1 177.3(3) . . . . ?
C10 C9 C22 F2 57.9(4) . . . . ?
C10 C9 C22 F3 -61.7(5) . . . . ?
C10 C11 C12 C13 -155.0(3) . . . . ?
C10 C11 C12 C17 27.1(4) . . . . ?
C11 O1 C8 C7 65.2(3) . . . . ?
C11 O1 C8 C9 -0.4(3) . . . . ?
C11 O1 C8 C21 -143.9(3) . . . . ?
C11 C12 C13 C14 -179.0(2) . . . . ?
C11 C12 C17 C16 179.0(2) . . . . ?
C11 C12 C17 C18 2.6(4) . . . . ?
C12 C13 C14 C15 0.1(3) . . . . ?
C12 C13 C14 C23 178.8(2) . . . . ?
C12 C17 C18 C19 161.4(3) . . . . ?
C13 C12 C17 C16 1.2(3) . . . . ?
C13 C12 C17 C18 -175.3(3) . . . . ?
C13 C14 C15 C16 1.0(3) . . . . ?
C13 C14 C23 C24 -114.7(3) . . . . ?
C13 C14 C23 C25 124.1(3) . . . . ?
C13 C14 C23 C26 3.0(4) . . . . ?
C14 C15 C16 C17 -0.9(3) . . . . ?
C14 C15 C16 C20 179.2(2) . . . . ?
C15 C14 C23 C24 63.9(3) . . . . ?
C15 C14 C23 C25 -57.2(3) . . . . ?
C15 C14 C23 C26 -178.4(3) . . . . ?
C15 C16 C17 C12 -0.2(3) . . . . ?
C15 C16 C17 C18 177.1(2) . . . . ?
C15 C16 C20 C19 -159.8(3) . . . . ?
C15 C16 C20 C27 82.4(3) . . . . ?
C15 C16 C20 C28 -39.0(3) . . . . ?
C16 C17 C18 C19 -15.3(3) . . . . ?
C17 C12 C13 C14 -1.2(3) . . . . ?
C17 C16 C20 C19 20.3(3) . . . . ?
C17 C16 C20 C27 -97.4(3) . . . . ?
C17 C16 C20 C28 141.1(2) . . . . ?
C17 C18 C19 C20 27.5(3) . . . . ?
C18 C19 C20 C16 -28.4(3) . . . . ?
C18 C19 C20 C27 87.9(3) . . . . ?
C18 C19 C20 C28 -149.3(3) . . . . ?
C20 C16 C17 C12 179.7(2) . . . . ?
C20 C16 C17 C18 -3.1(3) . . . . ?
C21 C8 C9 C7 -111.5(3) . . . . ?
C21 C8 C9 C10 135.5(3) . . . . ?
C21 C8 C9 C22 -2.3(5) . . . . ?
C22 C9 C10 C11 140.8(3) . . . . ?
C23 C14 C15 C16 -177.7(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
;
_oxdiff_exptl_absorpt_empirical_full_max 1.257
_oxdiff_exptl_absorpt_empirical_full_min 0.846
####################################################################### 
# 
# 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_202404129_twin1_hklf4
_database_code_depnum_ccdc_archive 'CCDC 2348513'
loop_
_audit_author_name
_audit_author_address
'Zhiyong Jiang'
;Henan Normal University
China
;
_audit_update_record             
;
2024-04-16 deposited with the CCDC.	2024-05-07 downloaded from the CCDC.
;
_audit_creation_date             2024-04-15
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H15 F3 O'
_chemical_formula_sum            'C18 H15 F3 O'
_chemical_formula_weight         304.30
_chemical_melting_point          ?
_chemical_oxdiff_formula         C20H20N4O4F3
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'
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      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                   6.9554(4)
_cell_length_b                   13.0085(7)
_cell_length_c                   17.4007(13)
_cell_angle_alpha                75.775(6)
_cell_angle_beta                 80.036(6)
_cell_angle_gamma                89.708(5)
_cell_volume                     1501.95(17)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3211
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      69.6650
_cell_measurement_theta_min      5.2840
_shelx_estimated_absorpt_T_max   0.931
_shelx_estimated_absorpt_T_min   0.846
_exptl_absorpt_coefficient_mu    0.912
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.94132
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.81a (Rigaku Oxford Diffraction, 2023)
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    1.346
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             632
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_av_unetI/netI     0.0416
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            8516
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.080
_diffrn_reflns_theta_max         67.080
_diffrn_reflns_theta_min         3.508
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2312
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -108.00 -35.00   1.00    1.50    --  -33.50 178.00  30.00   73
  2  ω   -108.00 -35.00   1.00    1.50    --  -33.50 178.00 -30.00   73
  3  ω   -104.00 -11.00   1.00    1.50    --  -33.50 -37.00-150.00   93
  4  ω   -103.00 -15.00   1.00    1.50    --  -33.50 149.00 145.00   88
  5  ω   -104.00 -11.00   1.00    1.50    --  -33.50 -37.00  90.00   93
  6  ω    -56.00  37.00   1.00    1.50    --  -33.50  37.00  30.00   93
  7  ω     36.00 106.00   1.00    1.50    --   36.47-149.00  98.00   70
  8  ω     61.00 110.00   1.00    1.50    --   36.47 178.00 -60.00   49
  9  ω     38.00 107.00   1.00   17.50    --  108.00 -94.00 -90.00   69
 10  ω     38.00 128.00   1.00   17.50    --  108.00 -45.00  60.00   90
 11  ω     61.00 146.00   1.00   17.50    --  108.00 178.00 -90.00   85
 12  ω     49.00 123.00   1.00   17.50    --  108.00 -45.00 -30.00   74
 13  ω    102.00 155.00   1.00   17.50    --  108.00  77.00 150.00   53
 14  ω    145.00 175.00   1.00   17.50    --  108.00 111.00  60.00   30
 15  ω    114.00 169.00   1.00   17.50    --  108.00  77.00  90.00   55
 16  ω     43.00  93.00   1.00   17.50    --  108.00 -94.00   0.00   50
 17  ω     66.00 109.00   1.00   17.50    --  108.00-111.00 150.00   43
 18  ω    129.00 175.00   1.00   17.50    --  108.00 111.00-150.00   46
 19  ω     88.00 176.00   1.00   17.50    --  108.00  45.00  30.00   88
 20  ω     89.00 172.00   1.00   17.50    --  108.00  61.00 120.00   83
 21  ω     43.00 106.00   1.00   17.50    --  108.00-111.00-120.00   63
 22  ω    101.00 169.00   1.00   17.50    --  108.00  77.00  60.00   68
 23  ω     74.00 108.00   1.00   17.50    --  108.00-111.00  60.00   34
 24  ω     98.00 145.00   1.00   17.50    --  108.00 123.00 -17.00   47
;
_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      0.2086409000
_diffrn_orient_matrix_UB_12      0.0009977000
_diffrn_orient_matrix_UB_13      -0.0477138000
_diffrn_orient_matrix_UB_21      0.0820367000
_diffrn_orient_matrix_UB_22      -0.0184886000
_diffrn_orient_matrix_UB_23      0.0788512000
_diffrn_orient_matrix_UB_31      -0.0197506000
_diffrn_orient_matrix_UB_32      -0.1208568000
_diffrn_orient_matrix_UB_33      0.0108833000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5199
_reflns_number_total             8516
_reflns_special_details          
;
 _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 1.171.42.81a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.81a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.81a (Rigaku OD, 2023)'
_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    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.238
_refine_diff_density_min         -0.280
_refine_diff_density_rms         0.051
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     402
_refine_ls_number_reflns         8516
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0797
_refine_ls_R_factor_gt           0.0513
_refine_ls_restrained_S_all      1.003
_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)+(0.0607P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1190
_refine_ls_wR_factor_ref         0.1277
_refine_special_details          
;
 Refined as a 2-component twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.5445(12)
 0.4555(12)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C3(H3), C5(H5), C8(H8), C11(H11), C12(H12), C13(H13), C14(H14),
 C15(H15), C1'(H1'), C3'(H3'), C5'(H5'), C8'(H8'), C11'(H11'), C12'(H12'),
 C13'(H13'), C14'(H14'), C15'(H15')
3.b Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C17(H17A,H17B,H17C), C16'(H16D,H16E,H16F), C17'(H17D,
 H17E,H17F)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.0806(5) 0.2112(3) 0.78119(19) 0.0566(7) Uani 1 1 d . . . . .
H1 H 0.0962 0.2824 0.7536 0.068 Uiso 1 1 calc R . . . .
C2 C -0.0547(5) 0.1872(3) 0.84777(19) 0.0596(7) Uani 1 1 d . . . . .
C3 C -0.1146(5) 0.0811(3) 0.89783(19) 0.0637(8) Uani 1 1 d . . . . .
H3 H -0.1601 0.0769 0.9521 0.076 Uiso 1 1 calc R . . . .
C4 C -0.1131(5) -0.0113(3) 0.8765(2) 0.0612(8) Uani 1 1 d . . . . .
C5 C -0.0412(4) -0.0216(3) 0.79593(19) 0.0561(7) Uani 1 1 d . . . . .
H5 H -0.0936 -0.0782 0.7813 0.067 Uiso 1 1 calc R . . . .
C6 C 0.0922(4) 0.0411(2) 0.74033(18) 0.0509(7) Uani 1 1 d . . . . .
C7 C 0.2108(4) 0.1359(3) 0.74578(18) 0.0528(7) Uani 1 1 d . . . . .
C8 C 0.2967(4) 0.1793(3) 0.65795(19) 0.0559(7) Uani 1 1 d . . . . .
H8 H 0.3722 0.2419 0.6370 0.067 Uiso 1 1 calc R . . . .
C9 C 0.2490(4) 0.1150(2) 0.61484(18) 0.0528(7) Uani 1 1 d . . . . .
C10 C 0.2927(4) 0.1193(3) 0.52916(18) 0.0545(7) Uani 1 1 d . . . . .
C11 C 0.2512(5) 0.0326(3) 0.5003(2) 0.0662(8) Uani 1 1 d . . . . .
H11 H 0.1939 -0.0294 0.5360 0.079 Uiso 1 1 calc R . . . .
C12 C 0.2951(5) 0.0387(3) 0.4188(2) 0.0753(10) Uani 1 1 d . . . . .
H12 H 0.2663 -0.0194 0.4000 0.090 Uiso 1 1 calc R . . . .
C13 C 0.3798(5) 0.1282(3) 0.3656(2) 0.0730(10) Uani 1 1 d . . . . .
H13 H 0.4093 0.1310 0.3109 0.088 Uiso 1 1 calc R . . . .
C14 C 0.4217(5) 0.2150(3) 0.3932(2) 0.0735(10) Uani 1 1 d . . . . .
H14 H 0.4789 0.2765 0.3569 0.088 Uiso 1 1 calc R . . . .
C15 C 0.3790(5) 0.2108(3) 0.4741(2) 0.0645(8) Uani 1 1 d . . . . .
H15 H 0.4080 0.2695 0.4922 0.077 Uiso 1 1 calc R . . . .
C16 C -0.1666(6) 0.2756(4) 0.8762(3) 0.0816(11) Uani 1 1 d . . . . .
H16A H -0.3038 0.2639 0.8783 0.122 Uiso 1 1 calc GR . . . .
H16B H -0.1236 0.3426 0.8393 0.122 Uiso 1 1 calc GR . . . .
H16C H -0.1432 0.2762 0.9288 0.122 Uiso 1 1 calc GR . . . .
C17 C -0.2016(6) -0.1111(4) 0.9365(2) 0.0831(11) Uani 1 1 d . . . . .
H17A H -0.3316 -0.1238 0.9284 0.125 Uiso 1 1 calc GR . . . .
H17B H -0.2063 -0.1031 0.9902 0.125 Uiso 1 1 calc GR . . . .
H17C H -0.1232 -0.1701 0.9292 0.125 Uiso 1 1 calc GR . . . .
C18 C 0.3772(5) 0.1037(3) 0.7922(2) 0.0604(8) Uani 1 1 d . . . . .
F1 F 0.3210(3) 0.05429(18) 0.86943(12) 0.0760(6) Uani 1 1 d . . . . .
F2 F 0.4884(3) 0.1886(2) 0.78978(15) 0.0886(7) Uani 1 1 d . . . . .
F3 F 0.4982(3) 0.0377(2) 0.76060(14) 0.0843(6) Uani 1 1 d . . . . .
O1 O 0.1313(3) 0.02859(17) 0.66264(12) 0.0586(5) Uani 1 1 d . . . . .
C1' C 0.8343(4) 0.2887(3) 0.21787(18) 0.0555(7) Uani 1 1 d . . . . .
H1' H 0.8256 0.2174 0.2455 0.067 Uiso 1 1 calc R . . . .
C2' C 0.7581(5) 0.3142(3) 0.15032(19) 0.0604(8) Uani 1 1 d . . . . .
C3' C 0.7448(5) 0.4195(3) 0.09995(19) 0.0617(8) Uani 1 1 d . . . . .
H3' H 0.7483 0.4235 0.0456 0.074 Uiso 1 1 calc R . . . .
C4' C 0.7281(5) 0.5125(3) 0.12070(18) 0.0590(8) Uani 1 1 d . . . . .
C5' C 0.7269(4) 0.5235(3) 0.20148(19) 0.0568(7) Uani 1 1 d . . . . .
H5' H 0.6625 0.5810 0.2152 0.068 Uiso 1 1 calc R . . . .
C6' C 0.8088(4) 0.4596(2) 0.25815(17) 0.0502(7) Uani 1 1 d . . . . .
C7' C 0.9329(4) 0.3646(2) 0.25354(17) 0.0503(7) Uani 1 1 d . . . . .
C8' C 0.9402(4) 0.3210(3) 0.34187(18) 0.0545(7) Uani 1 1 d . . . . .
H8' H 0.9970 0.2580 0.3635 0.065 Uiso 1 1 calc R . . . .
C9' C 0.8534(4) 0.3860(3) 0.38406(18) 0.0532(7) Uani 1 1 d . . . . .
C10' C 0.8185(4) 0.3816(3) 0.47017(18) 0.0538(7) Uani 1 1 d . . . . .
C11' C 0.7520(5) 0.4689(3) 0.4985(2) 0.0660(8) Uani 1 1 d . . . . .
H11' H 0.7277 0.5312 0.4624 0.079 Uiso 1 1 calc R . . . .
C12' C 0.7218(5) 0.4635(3) 0.5801(2) 0.0758(10) Uani 1 1 d . . . . .
H12' H 0.6776 0.5222 0.5985 0.091 Uiso 1 1 calc R . . . .
C13' C 0.7567(5) 0.3723(3) 0.6337(2) 0.0735(10) Uani 1 1 d . . . . .
H13' H 0.7367 0.3692 0.6885 0.088 Uiso 1 1 calc R . . . .
C14' C 0.8215(5) 0.2847(3) 0.6066(2) 0.0737(10) Uani 1 1 d . . . . .
H14' H 0.8437 0.2225 0.6432 0.088 Uiso 1 1 calc R . . . .
C15' C 0.8532(5) 0.2896(3) 0.5254(2) 0.0672(9) Uani 1 1 d . . . . .
H15' H 0.8983 0.2307 0.5074 0.081 Uiso 1 1 calc R . . . .
C16' C 0.6726(6) 0.2259(3) 0.1225(3) 0.0775(10) Uani 1 1 d . . . . .
H16D H 0.6824 0.1593 0.1602 0.116 Uiso 1 1 calc GR . . . .
H16E H 0.7434 0.2239 0.0704 0.116 Uiso 1 1 calc GR . . . .
H16F H 0.5378 0.2384 0.1192 0.116 Uiso 1 1 calc GR . . . .
C17' C 0.7001(7) 0.6137(4) 0.0592(2) 0.0890(12) Uani 1 1 d . . . . .
H17D H 0.5847 0.6468 0.0790 0.133 Uiso 1 1 calc GR . . . .
H17E H 0.6862 0.5972 0.0096 0.133 Uiso 1 1 calc GR . . . .
H17F H 0.8115 0.6612 0.0501 0.133 Uiso 1 1 calc GR . . . .
C18' C 1.1412(4) 0.3957(3) 0.2081(2) 0.0591(8) Uani 1 1 d . . . . .
F1' F 1.2327(3) 0.4599(2) 0.24054(14) 0.0853(7) Uani 1 1 d . . . . .
F2' F 1.2482(3) 0.3092(2) 0.21069(16) 0.0910(7) Uani 1 1 d . . . . .
F3' F 1.1545(3) 0.44489(19) 0.13089(12) 0.0781(6) Uani 1 1 d . . . . .
O1' O 0.7776(3) 0.47260(17) 0.33570(12) 0.0577(5) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 H1 0.9300 . ?
C1 C2 1.332(5) . ?
C1 C7 1.501(5) . ?
C2 C3 1.458(5) . ?
C2 C16 1.520(5) . ?
C3 H3 0.9300 . ?
C3 C4 1.342(5) . ?
C4 C5 1.443(5) . ?
C4 C17 1.509(5) . ?
C5 H5 0.9300 . ?
C5 C6 1.331(4) . ?
C6 C7 1.518(4) . ?
C6 O1 1.382(4) . ?
C7 C8 1.508(4) . ?
C7 C18 1.523(4) . ?
C8 H8 0.9300 . ?
C8 C9 1.330(4) . ?
C9 C10 1.456(4) . ?
C9 O1 1.393(4) . ?
C10 C11 1.392(5) . ?
C10 C15 1.394(5) . ?
C11 H11 0.9300 . ?
C11 C12 1.381(5) . ?
C12 H12 0.9300 . ?
C12 C13 1.360(6) . ?
C13 H13 0.9300 . ?
C13 C14 1.381(6) . ?
C14 H14 0.9300 . ?
C14 C15 1.376(5) . ?
C15 H15 0.9300 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 F1 1.330(4) . ?
C18 F2 1.340(4) . ?
C18 F3 1.346(4) . ?
C1' H1' 0.9300 . ?
C1' C2' 1.340(5) . ?
C1' C7' 1.513(4) . ?
C2' C3' 1.446(5) . ?
C2' C16' 1.512(5) . ?
C3' H3' 0.9300 . ?
C3' C4' 1.344(5) . ?
C4' C5' 1.446(5) . ?
C4' C17' 1.515(5) . ?
C5' H5' 0.9300 . ?
C5' C6' 1.332(4) . ?
C6' C7' 1.515(4) . ?
C6' O1' 1.381(4) . ?
C7' C8' 1.512(4) . ?
C7' C18' 1.529(4) . ?
C8' H8' 0.9300 . ?
C8' C9' 1.328(4) . ?
C9' C10' 1.463(4) . ?
C9' O1' 1.392(4) . ?
C10' C11' 1.392(5) . ?
C10' C15' 1.388(5) . ?
C11' H11' 0.9300 . ?
C11' C12' 1.383(5) . ?
C12' H12' 0.9300 . ?
C12' C13' 1.367(6) . ?
C13' H13' 0.9300 . ?
C13' C14' 1.381(6) . ?
C14' H14' 0.9300 . ?
C14' C15' 1.378(5) . ?
C15' H15' 0.9300 . ?
C16' H16D 0.9600 . ?
C16' H16E 0.9600 . ?
C16' H16F 0.9600 . ?
C17' H17D 0.9600 . ?
C17' H17E 0.9600 . ?
C17' H17F 0.9600 . ?
C18' F1' 1.334(4) . ?
C18' F2' 1.342(4) . ?
C18' F3' 1.326(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 H1 116.4 . . ?
C2 C1 C7 127.1(3) . . ?
C7 C1 H1 116.4 . . ?
C1 C2 C3 126.4(3) . . ?
C1 C2 C16 119.5(3) . . ?
C3 C2 C16 114.1(3) . . ?
C2 C3 H3 115.5 . . ?
C4 C3 C2 128.9(3) . . ?
C4 C3 H3 115.5 . . ?
C3 C4 C5 123.8(3) . . ?
C3 C4 C17 120.3(3) . . ?
C5 C4 C17 115.8(3) . . ?
C4 C5 H5 116.5 . . ?
C6 C5 C4 126.9(3) . . ?
C6 C5 H5 116.5 . . ?
C5 C6 C7 129.8(3) . . ?
C5 C6 O1 120.5(3) . . ?
O1 C6 C7 109.6(2) . . ?
C1 C7 C6 110.6(2) . . ?
C1 C7 C8 113.7(3) . . ?
C1 C7 C18 111.2(3) . . ?
C6 C7 C18 112.6(3) . . ?
C8 C7 C6 99.9(2) . . ?
C8 C7 C18 108.5(2) . . ?
C7 C8 H8 124.9 . . ?
C9 C8 C7 110.2(3) . . ?
C9 C8 H8 124.9 . . ?
C8 C9 C10 132.7(3) . . ?
C8 C9 O1 111.8(3) . . ?
O1 C9 C10 115.5(3) . . ?
C11 C10 C9 121.2(3) . . ?
C11 C10 C15 118.5(3) . . ?
C15 C10 C9 120.3(3) . . ?
C10 C11 H11 120.0 . . ?
C12 C11 C10 119.9(4) . . ?
C12 C11 H11 120.0 . . ?
C11 C12 H12 119.4 . . ?
C13 C12 C11 121.1(4) . . ?
C13 C12 H12 119.4 . . ?
C12 C13 H13 120.2 . . ?
C12 C13 C14 119.7(3) . . ?
C14 C13 H13 120.2 . . ?
C13 C14 H14 119.9 . . ?
C15 C14 C13 120.3(4) . . ?
C15 C14 H14 119.9 . . ?
C10 C15 H15 119.8 . . ?
C14 C15 C10 120.5(3) . . ?
C14 C15 H15 119.8 . . ?
C2 C16 H16A 109.5 . . ?
C2 C16 H16B 109.5 . . ?
C2 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C4 C17 H17A 109.5 . . ?
C4 C17 H17B 109.5 . . ?
C4 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
F1 C18 C7 114.7(3) . . ?
F1 C18 F2 106.9(3) . . ?
F1 C18 F3 105.6(3) . . ?
F2 C18 C7 110.9(3) . . ?
F2 C18 F3 105.9(3) . . ?
F3 C18 C7 112.3(3) . . ?
C6 O1 C9 108.0(2) . . ?
C2' C1' H1' 116.9 . . ?
C2' C1' C7' 126.2(3) . . ?
C7' C1' H1' 116.9 . . ?
C1' C2' C3' 126.9(3) . . ?
C1' C2' C16' 118.4(3) . . ?
C3' C2' C16' 114.8(3) . . ?
C2' C3' H3' 115.5 . . ?
C4' C3' C2' 129.0(3) . . ?
C4' C3' H3' 115.5 . . ?
C3' C4' C5' 123.9(3) . . ?
C3' C4' C17' 120.6(3) . . ?
C5' C4' C17' 115.5(3) . . ?
C4' C5' H5' 116.7 . . ?
C6' C5' C4' 126.5(3) . . ?
C6' C5' H5' 116.7 . . ?
C5' C6' C7' 129.7(3) . . ?
C5' C6' O1' 120.3(3) . . ?
O1' C6' C7' 109.9(2) . . ?
C1' C7' C6' 110.5(2) . . ?
C1' C7' C18' 111.4(3) . . ?
C6' C7' C18' 112.9(3) . . ?
C8' C7' C1' 113.2(3) . . ?
C8' C7' C6' 99.9(2) . . ?
C8' C7' C18' 108.5(2) . . ?
C7' C8' H8' 125.1 . . ?
C9' C8' C7' 109.9(3) . . ?
C9' C8' H8' 125.1 . . ?
C8' C9' C10' 132.5(3) . . ?
C8' C9' O1' 112.1(3) . . ?
O1' C9' C10' 115.4(3) . . ?
C11' C10' C9' 121.2(3) . . ?
C15' C10' C9' 120.1(3) . . ?
C15' C10' C11' 118.7(3) . . ?
C10' C11' H11' 119.8 . . ?
C12' C11' C10' 120.3(4) . . ?
C12' C11' H11' 119.8 . . ?
C11' C12' H12' 119.8 . . ?
C13' C12' C11' 120.3(4) . . ?
C13' C12' H12' 119.8 . . ?
C12' C13' H13' 120.0 . . ?
C12' C13' C14' 120.1(3) . . ?
C14' C13' H13' 120.0 . . ?
C13' C14' H14' 120.0 . . ?
C15' C14' C13' 120.0(4) . . ?
C15' C14' H14' 120.0 . . ?
C10' C15' H15' 119.7 . . ?
C14' C15' C10' 120.6(4) . . ?
C14' C15' H15' 119.7 . . ?
C2' C16' H16D 109.5 . . ?
C2' C16' H16E 109.5 . . ?
C2' C16' H16F 109.5 . . ?
H16D C16' H16E 109.5 . . ?
H16D C16' H16F 109.5 . . ?
H16E C16' H16F 109.5 . . ?
C4' C17' H17D 109.5 . . ?
C4' C17' H17E 109.5 . . ?
C4' C17' H17F 109.5 . . ?
H17D C17' H17E 109.5 . . ?
H17D C17' H17F 109.5 . . ?
H17E C17' H17F 109.5 . . ?
F1' C18' C7' 112.2(3) . . ?
F1' C18' F2' 106.6(3) . . ?
F2' C18' C7' 110.3(3) . . ?
F3' C18' C7' 114.8(3) . . ?
F3' C18' F1' 106.0(3) . . ?
F3' C18' F2' 106.4(3) . . ?
C6' O1' C9' 107.7(2) . . ?

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
C1 C2 C3 C4 -28.9(5) . . . . ?
C1 C7 C8 C9 -122.7(3) . . . . ?
C1 C7 C18 F1 60.6(4) . . . . ?
C1 C7 C18 F2 -60.6(4) . . . . ?
C1 C7 C18 F3 -178.8(3) . . . . ?
C2 C1 C7 C6 48.8(4) . . . . ?
C2 C1 C7 C8 160.2(3) . . . . ?
C2 C1 C7 C18 -77.1(4) . . . . ?
C2 C3 C4 C5 2.4(6) . . . . ?
C2 C3 C4 C17 -173.6(3) . . . . ?
C3 C4 C5 C6 26.3(5) . . . . ?
C4 C5 C6 C7 2.9(6) . . . . ?
C4 C5 C6 O1 -172.8(3) . . . . ?
C5 C6 C7 C1 -49.0(4) . . . . ?
C5 C6 C7 C8 -169.0(3) . . . . ?
C5 C6 C7 C18 76.0(4) . . . . ?
C5 C6 O1 C9 169.7(3) . . . . ?
C6 C7 C8 C9 -4.9(3) . . . . ?
C6 C7 C18 F1 -64.1(4) . . . . ?
C6 C7 C18 F2 174.7(3) . . . . ?
C6 C7 C18 F3 56.5(4) . . . . ?
C7 C1 C2 C3 -4.4(5) . . . . ?
C7 C1 C2 C16 177.4(3) . . . . ?
C7 C6 O1 C9 -6.8(3) . . . . ?
C7 C8 C9 C10 180.0(3) . . . . ?
C7 C8 C9 O1 1.3(4) . . . . ?
C8 C7 C18 F1 -173.7(3) . . . . ?
C8 C7 C18 F2 65.1(4) . . . . ?
C8 C7 C18 F3 -53.1(4) . . . . ?
C8 C9 C10 C11 169.5(3) . . . . ?
C8 C9 C10 C15 -10.1(5) . . . . ?
C8 C9 O1 C6 3.5(3) . . . . ?
C9 C10 C11 C12 -179.7(3) . . . . ?
C9 C10 C15 C14 179.6(3) . . . . ?
C10 C9 O1 C6 -175.5(2) . . . . ?
C10 C11 C12 C13 0.3(6) . . . . ?
C11 C10 C15 C14 0.1(5) . . . . ?
C11 C12 C13 C14 -0.4(6) . . . . ?
C12 C13 C14 C15 0.3(5) . . . . ?
C13 C14 C15 C10 -0.2(5) . . . . ?
C15 C10 C11 C12 -0.1(5) . . . . ?
C16 C2 C3 C4 149.4(4) . . . . ?
C17 C4 C5 C6 -157.6(3) . . . . ?
C18 C7 C8 C9 113.1(3) . . . . ?
O1 C6 C7 C1 127.0(3) . . . . ?
O1 C6 C7 C8 7.0(3) . . . . ?
O1 C6 C7 C18 -107.9(3) . . . . ?
O1 C9 C10 C11 -11.9(4) . . . . ?
O1 C9 C10 C15 168.6(3) . . . . ?
C1' C2' C3' C4' -29.5(5) . . . . ?
C1' C7' C8' C9' -122.6(3) . . . . ?
C1' C7' C18' F1' -177.9(3) . . . . ?
C1' C7' C18' F2' -59.2(4) . . . . ?
C1' C7' C18' F3' 61.0(4) . . . . ?
C2' C1' C7' C6' 48.9(4) . . . . ?
C2' C1' C7' C8' 160.0(3) . . . . ?
C2' C1' C7' C18' -77.4(4) . . . . ?
C2' C3' C4' C5' 2.2(5) . . . . ?
C2' C3' C4' C17' -175.1(3) . . . . ?
C3' C4' C5' C6' 26.2(5) . . . . ?
C4' C5' C6' C7' 4.2(5) . . . . ?
C4' C5' C6' O1' -172.6(3) . . . . ?
C5' C6' C7' C1' -50.5(4) . . . . ?
C5' C6' C7' C8' -169.9(3) . . . . ?
C5' C6' C7' C18' 75.1(4) . . . . ?
C5' C6' O1' C9' 170.7(3) . . . . ?
C6' C7' C8' C9' -5.1(3) . . . . ?
C6' C7' C18' F1' 57.1(4) . . . . ?
C6' C7' C18' F2' 175.7(3) . . . . ?
C6' C7' C18' F3' -64.1(4) . . . . ?
C7' C1' C2' C3' -3.6(5) . . . . ?
C7' C1' C2' C16' 177.5(3) . . . . ?
C7' C6' O1' C9' -6.7(3) . . . . ?
C7' C8' C9' C10' 179.4(3) . . . . ?
C7' C8' C9' O1' 1.6(4) . . . . ?
C8' C7' C18' F1' -52.6(4) . . . . ?
C8' C7' C18' F2' 66.1(4) . . . . ?
C8' C7' C18' F3' -173.8(3) . . . . ?
C8' C9' C10' C11' 169.1(3) . . . . ?
C8' C9' C10' C15' -10.3(5) . . . . ?
C8' C9' O1' C6' 3.2(3) . . . . ?
C9' C10' C11' C12' -179.3(3) . . . . ?
C9' C10' C15' C14' 179.8(3) . . . . ?
C10' C9' O1' C6' -175.0(2) . . . . ?
C10' C11' C12' C13' -0.1(6) . . . . ?
C11' C10' C15' C14' 0.3(5) . . . . ?
C11' C12' C13' C14' -0.3(6) . . . . ?
C12' C13' C14' C15' 0.7(5) . . . . ?
C13' C14' C15' C10' -0.7(5) . . . . ?
C15' C10' C11' C12' 0.1(5) . . . . ?
C16' C2' C3' C4' 149.5(3) . . . . ?
C17' C4' C5' C6' -156.3(3) . . . . ?
C18' C7' C8' C9' 113.1(3) . . . . ?
O1' C6' C7' C1' 126.6(3) . . . . ?
O1' C6' C7' C8' 7.1(3) . . . . ?
O1' C6' C7' C18' -107.9(3) . . . . ?
O1' C9' C10' C11' -13.1(4) . . . . ?
O1' C9' C10' C15' 167.5(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.117
_oxdiff_exptl_absorpt_empirical_full_min 0.898
_oxdiff_twin_integration_method  simultaneous
_oxdiff_twin_items               2
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
_oxdiff_twin_reflns_isolated
_oxdiff_twin_reflns_overlapped
_twin_individual_twin_lattice_type
_twin_individual_twin_matrix_11
_twin_individual_twin_matrix_12
_twin_individual_twin_matrix_13
_twin_individual_twin_matrix_21
_twin_individual_twin_matrix_22
_twin_individual_twin_matrix_23
_twin_individual_twin_matrix_31
_twin_individual_twin_matrix_32
_twin_individual_twin_matrix_33
1 0.5445(12) 4386 6543 ref 1.0000 0.0000 0.0000 0.0000 1.0000 0.0000 0.0000
0.0000 1.0000
2 0.4555(12) 4347 6543 nmt 1.0002 -0.0004 -0.0001 0.0170 -0.9994 -0.0004 0.8671
0.0007 -1.0002

_twin_special_details            
;
Component 2 rotated by 179.9685° 
around [0.92 0.01 0.40] (reciprocal) or [1.00 -0.00 0.00] (direct)
;
