# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_4f_pyre_auto
_database_code_depnum_ccdc_archive 'CCDC 2129411'
loop_
_audit_author_name
_audit_author_address
'Peng Hu'
;Northwest University
China
;
_audit_update_record             
;
2021-12-17 deposited with the CCDC.	2022-08-18 downloaded from the CCDC.
;
_audit_creation_date             2021-09-14
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.07.19 svn.r715e62df for OlexSys, GUI svn.r6383)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        pyrene-TFBQ
_chemical_formula_moiety         'C3 F2 O, C8 H5'
_chemical_formula_sum            'C11 H5 F2 O'
_chemical_formula_weight         191.15
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   7.78250(10)
_cell_length_b                   6.93350(10)
_cell_length_c                   14.69280(10)
_cell_angle_alpha                90
_cell_angle_beta                 94.8470(10)
_cell_angle_gamma                90
_cell_volume                     789.988(16)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9400
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      76.6670
_cell_measurement_theta_min      6.0340
_shelx_estimated_absorpt_T_max   0.988
_shelx_estimated_absorpt_T_min   0.944
_exptl_absorpt_coefficient_mu    1.161
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.89003
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'light brownish black'
_exptl_crystal_colour_lustre     light
_exptl_crystal_colour_modifier   brownish
_exptl_crystal_colour_primary    black
_exptl_crystal_density_diffrn    1.607
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             388
_exptl_crystal_preparation       ?
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Benzene'
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.01
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0225
_diffrn_reflns_av_unetI/netI     0.0115
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            14174
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        66.572
_diffrn_reflns_theta_max         66.572
_diffrn_reflns_theta_min         6.045
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     32.00 119.00   0.50    0.08    --   46.93  54.00  -4.00  174
  2  ω     91.00 178.00   0.50    0.30    --  108.75  61.00  60.00  174
  3  ω     94.00 178.00   0.50    0.30    --  108.75  45.00  90.00  168
  4  ω     92.00 178.00   0.50    0.30    --  108.75  54.00  -4.00  172
  5  ω     91.00 178.00   0.50    0.30    --  108.75  61.00 -90.00  174
  6  ω     23.00 119.00   0.50    0.08    --   46.93  77.00 -90.00  192
  7  ω    -23.00  29.00   0.50    0.08    --  -46.93  19.00 150.00  104
  8  ω    -68.00 -26.00   0.50    0.30    --  -99.00  61.00 120.00   84
  9  ω    -68.00 -26.00   0.50    0.30    --  -99.00  61.00  90.00   84
 10  ω    -58.00 -26.00   0.50    0.30    --  -99.00  54.00  -4.00   64
 11  ω    -68.00 -26.00   0.50    0.30    --  -99.00  61.00-180.00   84
 12  ω    -58.00  26.00   0.50    0.08    --  -46.93  54.00  -4.00  168
 13  ω   -121.00 -32.00   0.50    0.08    --  -46.93 -37.00  60.00  178
 14  ω   -119.00 -31.00   0.50    0.08    --  -46.93 -57.00 150.00  176
 15  ω   -172.00 -75.00   0.50    0.30    --  -99.00 -77.00 120.00  194
 16  ω   -172.00 -81.00   0.50    0.30    --  -99.00 -61.00 120.00  182
 17  ω   -172.00 -81.00   0.50    0.30    --  -99.00 -61.00  30.00  182
 18  ω   -172.00 -81.00   0.50    0.30    --  -99.00 -61.00  60.00  182
 19  ω   -171.00 -84.00   0.50    0.30    --  -99.00 -45.00 150.00  174
 20  ω   -171.00 -84.00   0.50    0.30    --  -99.00 -45.00 120.00  174
 21  ω   -171.00 -84.00   0.50    0.30    --  -99.00 -45.00  90.00  174
 22  ω   -171.00 -84.00   0.50    0.30    --  -99.00 -45.00  60.00  174
 23  ω   -174.00 -83.00   0.50    0.30    --  -99.00 -30.00  60.00  182
 24  ω   -174.00 -81.00   0.50    0.30    --  -99.00 -15.00  90.00  186
 25  ω   -172.00 -82.00   0.50    0.30    --  -99.00 -54.00-147.00  180
 26  ω   -119.00 -31.00   0.50    0.08    --  -46.93 -54.00-147.00  176
 27  ω    -28.00  30.00   0.50    0.08    --   46.93 -19.00-150.00  116
 28  ω     36.00  75.00   0.50    0.30    --  108.75 -61.00 -90.00   78
 29  ω     36.00 109.00   0.50    0.30    --  108.75 -77.00 -90.00  146
 30  ω     36.00  75.00   0.50    0.30    --  108.75 -61.00 -60.00   78
 31  ω     36.00  75.00   0.50    0.30    --  108.75 -61.00 -30.00   78
 32  ω     36.00  65.00   0.50    0.30    --  108.75 -54.00-147.00   58
 33  ω    -25.00  62.00   0.50    0.08    --   46.93 -54.00-147.00  174
 34  ω     36.00  75.00   0.50    0.30    --  108.75 -61.00  60.00   78
 35  ω     36.00  75.00   0.50    0.30    --  108.75 -61.00 150.00   78
 36  ω     36.00  75.00   0.50    0.30    --  108.75 -61.00  90.00   78
 37  ω     36.00 106.00   0.50    0.30    --  108.75 -94.00  30.00  140
 38  ω     36.00 112.00   0.50    0.30    --  108.75-125.00 -90.00  152
 39  ω     36.00 112.00   0.50    0.30    --  108.75-125.00-120.00  152
 40  ω     36.00 106.00   0.50    0.30    --  108.75 -94.00 -60.00  140
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1673233000
_diffrn_orient_matrix_UB_12      -0.0349027000
_diffrn_orient_matrix_UB_13      -0.0465913000
_diffrn_orient_matrix_UB_21      -0.0622981000
_diffrn_orient_matrix_UB_22      0.1411926000
_diffrn_orient_matrix_UB_23      -0.0767512000
_diffrn_orient_matrix_UB_31      0.0871143000
_diffrn_orient_matrix_UB_32      0.1680213000
_diffrn_orient_matrix_UB_33      0.0548411000
_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              'PhotonJet R (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1299
_reflns_number_total             1398
_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 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.230
_refine_diff_density_min         -0.146
_refine_diff_density_rms         0.038
_refine_ls_extinction_coef       0.0015(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     128
_refine_ls_number_reflns         1398
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0299
_refine_ls_R_factor_gt           0.0279
_refine_ls_restrained_S_all      1.083
_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)+(0.0452P)²+0.2538P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0807
_refine_ls_wR_factor_ref         0.0826
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C6(H6), C5(H5), C4(H4)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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 0.52278(9) 0.51789(10) 0.68733(4) 0.0269(2) Uani 1 1 d . . . . .
F2 F 0.22574(9) 0.63276(10) 0.58815(5) 0.0268(2) Uani 1 1 d . . . . .
O1 O 0.79009(11) 0.39393(13) 0.59610(6) 0.0275(2) Uani 1 1 d . . . . .
C8 C 0.43497(14) 0.03252(15) 0.52788(8) 0.0182(3) Uani 1 1 d . . . . .
C10 C 0.50561(15) 0.51185(16) 0.59667(8) 0.0203(3) Uani 1 1 d . . . . .
C7 C 0.27320(15) 0.09776(16) 0.48651(8) 0.0209(3) Uani 1 1 d . . . . .
C11 C 0.36182(15) 0.56699(17) 0.54864(8) 0.0202(3) Uani 1 1 d . . . . .
C3 C 0.46683(16) 0.03365(16) 0.62457(8) 0.0214(3) Uani 1 1 d . . . . .
C9 C 0.65796(15) 0.44095(16) 0.55254(8) 0.0203(3) Uani 1 1 d . . . . .
C1 C 0.75476(16) -0.09413(17) 0.61158(9) 0.0244(3) Uani 1 1 d . . . . .
H1 H 0.862416 -0.136383 0.639948 0.029 Uiso 1 1 calc R U . . .
C2 C 0.63192(16) -0.03222(18) 0.66434(8) 0.0251(3) Uani 1 1 d . . . . .
H2 H 0.654851 -0.032133 0.728884 0.030 Uiso 1 1 calc R U . . .
C6 C 0.14888(16) 0.16403(17) 0.54221(9) 0.0262(3) Uani 1 1 d . . . . .
H6 H 0.041220 0.209420 0.515187 0.031 Uiso 1 1 calc R U . . .
C5 C 0.18071(17) 0.16434(18) 0.63634(9) 0.0291(3) Uani 1 1 d . . . . .
H5 H 0.094529 0.209457 0.673202 0.035 Uiso 1 1 calc R U . . .
C4 C 0.33734(18) 0.09938(18) 0.67745(8) 0.0276(3) Uani 1 1 d . . . . .
H4 H 0.356796 0.099562 0.742163 0.033 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 C10 1.3281(13) . ?
F2 C11 1.3306(14) . ?
O1 C9 1.2091(15) . ?
C8 C8 1.428(2) 3_656 ?
C8 C7 1.4247(17) . ?
C8 C3 1.4214(17) . ?
C10 C11 1.3278(17) . ?
C10 C9 1.4825(17) . ?
C7 C1 1.4395(17) 3_656 ?
C7 C6 1.3967(18) . ?
C11 C9 1.4825(17) 3_666 ?
C3 C2 1.4402(18) . ?
C3 C4 1.3998(18) . ?
C1 H1 0.9500 . ?
C1 C2 1.3507(19) . ?
C2 H2 0.9500 . ?
C6 H6 0.9500 . ?
C6 C5 1.3842(19) . ?
C5 H5 0.9500 . ?
C5 C4 1.389(2) . ?
C4 H4 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
C7 C8 C8 119.95(13) . 3_656 ?
C3 C8 C8 120.19(13) . 3_656 ?
C3 C8 C7 119.86(11) . . ?
F1 C10 C9 115.63(10) . . ?
C11 C10 F1 122.20(11) . . ?
C11 C10 C9 122.17(11) . . ?
C8 C7 C1 118.35(11) . 3_656 ?
C6 C7 C8 119.04(11) . . ?
C6 C7 C1 122.60(11) . 3_656 ?
F2 C11 C9 115.54(10) . 3_666 ?
C10 C11 F2 122.20(11) . . ?
C10 C11 C9 122.25(11) . 3_666 ?
C8 C3 C2 118.56(11) . . ?
C4 C3 C8 118.93(11) . . ?
C4 C3 C2 122.51(11) . . ?
O1 C9 C10 122.26(11) . . ?
O1 C9 C11 122.16(11) . 3_666 ?
C10 C9 C11 115.58(10) . 3_666 ?
C7 C1 H1 119.1 3_656 . ?
C2 C1 C7 121.72(11) . 3_656 ?
C2 C1 H1 119.1 . . ?
C3 C2 H2 119.4 . . ?
C1 C2 C3 121.22(11) . . ?
C1 C2 H2 119.4 . . ?
C7 C6 H6 119.6 . . ?
C5 C6 C7 120.77(12) . . ?
C5 C6 H6 119.6 . . ?
C6 C5 H5 119.7 . . ?
C6 C5 C4 120.69(12) . . ?
C4 C5 H5 119.7 . . ?
C3 C4 H4 119.6 . . ?
C5 C4 C3 120.71(11) . . ?
C5 C4 H4 119.6 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
F1 C10 C11 F2 0.32(18) . . . . ?
F1 C10 C11 C9 -179.57(10) . . . 3_666 ?
F1 C10 C9 O1 -0.90(17) . . . . ?
F1 C10 C9 C11 179.60(9) . . . 3_666 ?
C8 C8 C7 C1 0.59(19) 3_656 . . 3_656 ?
C8 C8 C7 C6 -178.86(12) 3_656 . . . ?
C8 C8 C3 C2 -0.12(19) 3_656 . . . ?
C8 C8 C3 C4 179.58(13) 3_656 . . . ?
C8 C7 C6 C5 -0.84(18) . . . . ?
C8 C3 C2 C1 -0.03(18) . . . . ?
C8 C3 C4 C5 -0.63(18) . . . . ?
C7 C8 C3 C2 -179.68(10) . . . . ?
C7 C8 C3 C4 0.02(17) . . . . ?
C7 C1 C2 C3 -0.14(18) 3_656 . . . ?
C7 C6 C5 C4 0.24(19) . . . . ?
C11 C10 C9 O1 178.65(11) . . . . ?
C11 C10 C9 C11 -0.86(19) . . . 3_666 ?
C3 C8 C7 C1 -179.84(10) . . . 3_656 ?
C3 C8 C7 C6 0.71(17) . . . . ?
C9 C10 C11 F2 -179.20(10) . . . . ?
C9 C10 C11 C9 0.9(2) . . . 3_666 ?
C1 C7 C6 C5 179.73(11) 3_656 . . . ?
C2 C3 C4 C5 179.06(12) . . . . ?
C6 C5 C4 C3 0.51(19) . . . . ?
C4 C3 C2 C1 -179.72(11) . . . . ?


_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 1.217
_oxdiff_exptl_absorpt_empirical_full_min 0.869
####################################################################### 
# 
# 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_59_auto
_database_code_depnum_ccdc_archive 'CCDC 2129518'
loop_
_audit_author_name
_audit_author_address
'Peng Hu'
;Northwest University
China
;
_audit_update_record             
;
2021-12-17 deposited with the CCDC.	2022-08-18 downloaded from the CCDC.
;
_audit_creation_date             2021-04-25
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        chrysene-TFBQ
_chemical_formula_moiety         'C3 F2 O, C9 H6'
_chemical_formula_sum            'C12 H6 F2 O'
_chemical_formula_weight         204.17
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   6.61510(10)
_cell_length_b                   6.93080(10)
_cell_length_c                   18.4853(2)
_cell_angle_alpha                90
_cell_angle_beta                 93.4820(10)
_cell_angle_gamma                90
_cell_volume                     845.95(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    11327
_cell_measurement_temperature    149.99(10)
_cell_measurement_theta_max      77.0520
_cell_measurement_theta_min      4.7640
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.127
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.81743
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'light brownish black'
_exptl_crystal_colour_lustre     light
_exptl_crystal_colour_modifier   brownish
_exptl_crystal_colour_primary    black
_exptl_crystal_density_diffrn    1.603
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             416
_exptl_crystal_preparation       ?
_exptl_crystal_recrystallization_method 'slowing cooling by chlorobezene'
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0235
_diffrn_reflns_av_unetI/netI     0.0113
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            14793
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        66.595
_diffrn_reflns_theta_max         66.595
_diffrn_reflns_theta_min         4.793
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      149.99(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     30.00 119.00   0.50    0.05    --   46.43  57.00 150.00  178
  2  ω     23.00 119.00   0.50    0.05    --   46.43  77.00  30.00  192
  3  ω     30.00 119.00   0.50    0.05    --   46.43  57.00  30.00  178
  4  ω     23.00 119.00   0.50    0.05    --   46.43  77.00 -60.00  192
  5  ω     23.00 119.00   0.50    0.05    --   46.43  77.00-150.00  192
  6  ω    -39.00  28.00   0.50    0.05    --  -46.43  37.00 -30.00  134
  7  ω    -68.00 -26.00   0.50    0.05    --  -99.00  61.00-150.00   84
  8  ω    -39.00  28.00   0.50    0.05    --  -46.43  37.00  90.00  134
  9  ω     94.00 178.00   0.50    0.05    --  108.75  45.00-180.00  168
 10  ω     91.00 178.00   0.50    0.05    --  108.75  61.00-150.00  174
 11  ω     94.00 178.00   0.50    0.05    --  108.75  45.00 -60.00  168
 12  ω     85.00 178.00   0.50    0.05    --  108.75  77.00   0.00  186
 13  ω     91.00 178.00   0.50    0.05    --  108.75  61.00 120.00  174
 14  ω     36.00 109.00   0.50    0.05    --  108.75 -77.00-120.00  146
 15  ω     36.00  75.00   0.50    0.05    --  108.75 -61.00-180.00   78
 16  ω     36.00  75.00   0.50    0.05    --  108.75 -61.00 -60.00   78
 17  ω    -29.00  30.00   0.50    0.05    --   46.43 -19.00 -90.00  118
 18  ω    -25.00  63.00   0.50    0.05    --   46.43 -57.00-180.00  176
 19  ω     19.00  95.00   0.50    0.05    --   46.43-125.00-150.00  152
 20  ω     36.00 112.00   0.50    0.05    --  108.75-125.00  30.00  152
 21  ω     36.00 106.00   0.50    0.05    --  108.75 -94.00  30.00  140
 22  ω     36.00 112.00   0.50    0.05    --  108.75-125.00 120.00  152
 23  ω     36.00 112.00   0.50    0.05    --  108.75-125.00 150.00  152
 24  ω     36.00 106.00   0.50    0.05    --  108.75 -94.00 120.00  140
 25  ω   -112.00 -26.00   0.50    0.05    --  -99.00 125.00-150.00  172
 26  ω   -112.00 -26.00   0.50    0.05    --  -99.00 125.00-120.00  172
 27  ω   -112.00 -26.00   0.50    0.05    --  -99.00 125.00 150.00  172
 28  ω   -122.00 -31.00   0.50    0.05    --  -46.43 -19.00 -60.00  182
 29  ω   -119.00 -23.00   0.50    0.05    --  -46.43 -77.00-180.00  192
 30  ω   -119.00 -23.00   0.50    0.05    --  -46.43 -77.00  90.00  192
 31  ω   -172.00 -83.00   0.50    0.05    --  -99.00 -53.00 143.35  178
 32  ω   -172.00 -79.00   0.50    0.05    --  -99.00 -68.00 101.50  186
 33  ω   -172.00 -80.00   0.50    0.05    --  -99.00 -66.00  56.73  184
 34  ω   -172.00 -83.00   0.50    0.05    --  -99.00 -56.00 132.15  178
 35  ω   -172.00 -81.00   0.50    0.05    --  -99.00 -61.00  30.00  182
 36  ω   -172.00 -78.00   0.50    0.05    --  -99.00 -71.00 -41.33  188
 37  ω   -172.00-110.00   0.50    0.05    --  -99.00 -61.00 -90.00  124
 38  ω   -119.00 -74.00   0.50    0.05    --  -46.43-125.00 -90.00   90
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0854914000
_diffrn_orient_matrix_UB_12      -0.2068061000
_diffrn_orient_matrix_UB_13      -0.0024742000
_diffrn_orient_matrix_UB_21      -0.2151570000
_diffrn_orient_matrix_UB_22      0.0805155000
_diffrn_orient_matrix_UB_23      0.0064627000
_diffrn_orient_matrix_UB_31      -0.0284948000
_diffrn_orient_matrix_UB_32      0.0121407000
_diffrn_orient_matrix_UB_33      -0.0832338000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'PhotonJet R (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1388
_reflns_number_total             1492
_reflns_odcompleteness_completeness 99.89
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     69.95
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.223
_refine_diff_density_min         -0.194
_refine_diff_density_rms         0.042
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     136
_refine_ls_number_reflns         1492
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0318
_refine_ls_R_factor_gt           0.0299
_refine_ls_restrained_S_all      1.047
_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)+(0.0501P)²+0.2333P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0841
_refine_ls_wR_factor_ref         0.0859
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C008(H008), C009(H009), C00B(H00B), C00D(H00D), C00E(H00E), C00F(H00F)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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
F001 F 0.80139(9) 0.62328(10) 0.41530(4) 0.0308(2) Uani 1 1 d . . . . .
F002 F 0.44611(10) 0.48566(10) 0.35198(3) 0.0303(2) Uani 1 1 d . . . . .
O003 O 0.84527(11) 0.63664(12) 0.56216(5) 0.0294(2) Uani 1 1 d . . . . .
C004 C 0.08016(15) 0.46760(14) -0.02059(6) 0.0190(3) Uani 1 1 d . . . . .
C005 C 0.12215(17) 0.45326(15) 0.13370(6) 0.0221(3) Uani 1 1 d . . . . .
C006 C -0.05952(16) 0.52615(15) 0.09915(6) 0.0201(3) Uani 1 1 d . . . . .
C007 C 0.68868(16) 0.57434(15) 0.53375(6) 0.0216(3) Uani 1 1 d . . . . .
C008 C 0.26049(16) 0.39584(15) 0.01670(6) 0.0207(3) Uani 1 1 d . . . . .
H008 H 0.368868 0.352086 -0.010502 0.025 Uiso 1 1 calc R . . . .
C009 C 0.27982(16) 0.38903(15) 0.09004(6) 0.0223(3) Uani 1 1 d . . . . .
H009 H 0.401570 0.340205 0.113053 0.027 Uiso 1 1 calc R . . . .
C00A C 0.47911(17) 0.49499(15) 0.42322(6) 0.0216(3) Uani 1 1 d . . . . .
C00B C -0.21274(17) 0.58956(16) 0.14401(6) 0.0241(3) Uani 1 1 d . . . . .
H00B H -0.334947 0.641282 0.122393 0.029 Uiso 1 1 calc R . . . .
C00C C 0.65134(16) 0.56204(16) 0.45449(6) 0.0217(3) Uani 1 1 d . . . . .
C00D C -0.00765(19) 0.50303(17) 0.25161(6) 0.0298(3) Uani 1 1 d . . . . .
H00D H 0.008388 0.494580 0.302929 0.036 Uiso 1 1 calc R . . . .
C00E C -0.18761(19) 0.57753(17) 0.21803(7) 0.0289(3) Uani 1 1 d . . . . .
H00E H -0.292852 0.619954 0.246962 0.035 Uiso 1 1 calc R . . . .
C00F C 0.14398(18) 0.44289(17) 0.20987(6) 0.0271(3) Uani 1 1 d . . . . .
H00F H 0.265833 0.393383 0.232569 0.033 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F001 C00C 1.3332(13) . ?
F002 C00A 1.3233(13) . ?
O003 C007 1.2121(14) . ?
C004 C004 1.416(2) 3_565 ?
C004 C006 1.4510(16) 3_565 ?
C004 C008 1.4303(16) . ?
C005 C006 1.4192(16) . ?
C005 C009 1.4282(16) . ?
C005 C00F 1.4085(16) . ?
C006 C00B 1.4178(16) . ?
C007 C00A 1.4842(16) 3_666 ?
C007 C00C 1.4735(17) . ?
C008 H008 0.9500 . ?
C008 C009 1.3548(16) . ?
C009 H009 0.9500 . ?
C00A C00C 1.3296(17) . ?
C00B H00B 0.9500 . ?
C00B C00E 1.3708(17) . ?
C00D H00D 0.9500 . ?
C00D C00E 1.4068(18) . ?
C00D C00F 1.3672(17) . ?
C00E H00E 0.9500 . ?
C00F H00F 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
C004 C004 C006 120.05(12) 3_565 3_565 ?
C004 C004 C008 118.78(13) 3_565 . ?
C008 C004 C006 121.18(10) . 3_565 ?
C006 C005 C009 118.96(10) . . ?
C00F C005 C006 120.04(10) . . ?
C00F C005 C009 120.99(10) . . ?
C005 C006 C004 119.12(10) . 3_565 ?
C00B C006 C004 123.30(10) . 3_565 ?
C00B C006 C005 117.58(10) . . ?
O003 C007 C00A 122.03(11) . 3_666 ?
O003 C007 C00C 122.60(10) . . ?
C00C C007 C00A 115.37(10) . 3_666 ?
C004 C008 H008 119.3 . . ?
C009 C008 C004 121.30(10) . . ?
C009 C008 H008 119.3 . . ?
C005 C009 H009 119.1 . . ?
C008 C009 C005 121.79(10) . . ?
C008 C009 H009 119.1 . . ?
F002 C00A C007 115.71(10) . 3_666 ?
F002 C00A C00C 122.33(10) . . ?
C00C C00A C007 121.95(11) . 3_666 ?
C006 C00B H00B 119.4 . . ?
C00E C00B C006 121.15(11) . . ?
C00E C00B H00B 119.4 . . ?
F001 C00C C007 115.88(10) . . ?
C00A C00C F001 121.45(11) . . ?
C00A C00C C007 122.68(10) . . ?
C00E C00D H00D 120.2 . . ?
C00F C00D H00D 120.2 . . ?
C00F C00D C00E 119.54(11) . . ?
C00B C00E C00D 120.72(11) . . ?
C00B C00E H00E 119.6 . . ?
C00D C00E H00E 119.6 . . ?
C005 C00F H00F 119.5 . . ?
C00D C00F C005 120.96(11) . . ?
C00D C00F H00F 119.5 . . ?

_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 1.371
_oxdiff_exptl_absorpt_empirical_full_min 0.776
####################################################################### 
# 
# 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_171_auto
_database_code_depnum_ccdc_archive 'CCDC 2129516'
loop_
_audit_author_name
_audit_author_address
'Peng Hu'
;Northwest University
China
;
_audit_update_record             
;
2021-12-17 deposited with the CCDC.	2022-08-18 downloaded from the CCDC.
;
_audit_creation_date             2021-12-17
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        BA-TFBQ
_chemical_formula_moiety         '0.5(C6 F4 O2), 0.5(C18 H12)'
_chemical_formula_sum            'C12 H6 F2 O'
_chemical_formula_weight         204.17
_chemical_absolute_configuration ?
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   6.67424(4)
_cell_length_b                   7.45602(5)
_cell_length_c                   17.58647(11)
_cell_angle_alpha                90
_cell_angle_beta                 91.9097(6)
_cell_angle_gamma                90
_cell_volume                     874.674(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    19978
_cell_measurement_temperature    120.01(10)
_cell_measurement_theta_max      77.2990
_cell_measurement_theta_min      2.5070
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.090
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.72538
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'metallic dark black'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    black
_exptl_crystal_density_diffrn    1.550
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_recrystallization_method 'slowing cooling by chlorobezene'
_exptl_crystal_description       plate
_exptl_crystal_F_000             416
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0217
_diffrn_reflns_av_unetI/netI     0.0116
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            21103
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        66.600
_diffrn_reflns_theta_max         66.600
_diffrn_reflns_theta_min         2.514
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      120.01(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     85.00 178.00   0.50    0.05    --  108.75  77.00   0.00  186
  2  ω     91.00 178.00   0.50    0.05    --  108.75  61.00  60.00  174
  3  ω     94.00 176.00   0.50    0.05    --  108.75  45.00 150.00  164
  4  ω     85.00 113.00   0.50    0.05    --  108.75  77.00  30.00   56
  5  ω    106.00 131.00   0.50    0.05    --  108.75  45.00 120.00   50
  6  ω    138.00 165.00   0.50    0.05    --  108.75  45.00 120.00   54
  7  ω    133.00 159.00   0.50    0.05    --  108.75  30.00  90.00   52
  8  ω    148.00 173.00   0.50    0.05    --  108.75  30.00  60.00   50
  9  ω     93.00 178.00   0.50    0.05    --  108.75  30.00 120.00  170
 10  ω     95.00 168.00   0.50    0.05    --  108.75  61.00  30.00  146
 11  ω     93.00 178.00   0.50    0.05    --  108.75  30.00 -60.00  170
 12  ω     89.00 115.00   0.50    0.05    --  108.75  77.00-150.00   52
 13  ω     91.00 178.00   0.50    0.05    --  108.75  61.00-150.00  174
 14  ω    116.00 178.00   0.50    0.05    --  108.75  30.00-180.00  124
 15  ω    146.00 175.00   0.50    0.05    --  108.75  15.00-120.00   58
 16  ω     95.00 141.00   0.50    0.05    --  108.75  15.00-120.00   92
 17  ω     36.00 136.00   0.50    0.05    --  108.75 -84.00  70.61  200
 18  ω     36.00 112.00   0.50    0.05    --  108.75-125.00  60.00  152
 19  ω     36.00 133.00   0.50    0.05    --  108.75-157.00  66.00  194
 20  ω     36.00 112.00   0.50    0.05    --  108.75-125.00 120.00  152
 21  ω     36.00 116.00   0.50    0.05    --   46.82-157.00  66.00  160
 22  ω     64.00 108.00   0.50    0.05    --  108.75-125.00  90.00   88
 23  ω     36.00 112.00   0.50    0.05    --  108.75-125.00  30.00  152
 24  ω     62.00 101.00   0.50    0.05    --  108.75-125.00   0.00   78
 25  ω     15.00  93.00   0.50    0.05    --   46.82-119.00-138.00  156
 26  ω     36.00 112.00   0.50    0.05    --  108.75-125.00-180.00  152
 27  ω     75.00 106.00   0.50    0.05    --  108.75-100.00-153.11   62
 28  ω     36.00 106.00   0.50    0.05    --  108.75 -94.00-150.00  140
 29  ω     36.00 110.00   0.50    0.05    --  108.75-119.00-138.00  148
 30  ω     78.00 107.00   0.50    0.05    --  108.75-105.00-136.59   58
 31  ω     36.00  68.00   0.50    0.05    --  108.75-105.00-136.59   64
 32  ω     36.00 137.00   0.50    0.05    --  108.75 -87.00-142.15  202
 33  ω     58.00 100.00   0.50    0.05    --  108.75 -94.00 -60.00   84
 34  ω     36.00 106.00   0.50    0.05    --  108.75 -94.00 120.00  140
 35  ω     36.00  69.00   0.50    0.05    --  108.75 -94.00  90.00   66
 36  ω     38.00  64.00   0.50    0.05    --  108.75 -94.00  30.00   52
 37  ω     44.00  70.00   0.50    0.05    --  108.75 -58.00-103.92   52
 38  ω     49.00  75.00   0.50    0.05    --  108.75 -77.00 -90.00   52
 39  ω     36.00  75.00   0.50    0.05    --  108.75 -61.00-120.00   78
 40  ω     79.00 104.00   0.50    0.05    --  108.75 -77.00-150.00   50
 41  ω     36.00  75.00   0.50    0.05    --  108.75 -61.00 -90.00   78
 42  ω     36.00  75.00   0.50    0.05    --  108.75 -61.00-150.00   78
 43  ω     36.00  75.00   0.50    0.05    --  108.75 -61.00   0.00   78
 44  ω     36.00  75.00   0.50    0.05    --  108.75 -61.00  30.00   78
 45  ω     36.00  75.00   0.50    0.05    --  108.75 -61.00  90.00   78
 46  ω     41.00  70.00   0.50    0.05    --  108.75 -70.00 147.36   58
 47  ω    -28.00  30.00   0.50    0.05    --   46.82 -19.00-180.00  116
 48  ω     84.00 178.00   0.50    0.05    --  108.75 119.00 -53.00  188
 49  ω     58.00 120.00   0.50    0.05    --   46.82 157.00 101.00  124
 50  ω    -23.00  29.00   0.50    0.05    --  -46.82  19.00  90.00  104
 51  ω    -23.00  29.00   0.50    0.05    --  -46.82  19.00 -60.00  104
 52  ω    -23.00  29.00   0.50    0.05    --  -46.82  19.00-120.00  104
 53  ω   -108.00 -26.00   0.50    0.05    --  -99.00 111.00-122.15  164
 54  ω   -110.00 -26.00   0.50    0.05    --  -99.00 119.00 -53.00  168
 55  ω   -133.00 -30.00   0.50    0.05    --  -99.00 157.00 101.00  206
 56  ω   -125.00 -26.00   0.50    0.05    --  -99.00 143.00 -43.95  198
 57  ω   -112.00 -26.00   0.50    0.05    --  -99.00 125.00-120.00  172
 58  ω   -172.00 -78.00   0.50    0.05    --  -99.00-119.00-138.00  188
 59  ω   -120.00 -74.00   0.50    0.05    --  -46.82-125.00 -60.00   92
 60  ω   -120.00 -74.00   0.50    0.05    --  -46.82-125.00   0.00   92
 61  ω   -120.00 -74.00   0.50    0.05    --  -46.82-125.00  30.00   92
 62  ω   -120.00 -52.00   0.50    0.05    --  -46.82-157.00  66.00  136
 63  ω   -160.00 -52.00   0.50    0.05    --  -99.00-157.00  66.00  216
 64  ω   -120.00 -74.00   0.50    0.05    --  -46.82-125.00-120.00   92
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0313629000
_diffrn_orient_matrix_UB_12      -0.0209055000
_diffrn_orient_matrix_UB_13      -0.0867415000
_diffrn_orient_matrix_UB_21      0.0329876000
_diffrn_orient_matrix_UB_22      -0.2037663000
_diffrn_orient_matrix_UB_23      0.0075616000
_diffrn_orient_matrix_UB_31      -0.2264225000
_diffrn_orient_matrix_UB_32      -0.0269053000
_diffrn_orient_matrix_UB_33      0.0101303000
_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              'PhotonJet R (Cu) X-ray Source'
_reflns_Friedel_coverage         0.846
_reflns_Friedel_fraction_full    0.995
_reflns_Friedel_fraction_max     0.995
_reflns_number_gt                3042
_reflns_number_total             3064
_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 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.461
_refine_diff_density_min         -0.184
_refine_diff_density_rms         0.043
_refine_ls_abs_structure_details 
;
 Flack x determined using 1377 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.02(4)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     271
_refine_ls_number_reflns         3064
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0365
_refine_ls_R_factor_gt           0.0364
_refine_ls_restrained_S_all      1.066
_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)+(0.0599P)²+0.3532P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1004
_refine_ls_wR_factor_ref         0.1005
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C18(H18), C13(H13), C1(H1), C11(H11), C3(H3), C16(H16), C15(H15), C6(H6),
 C10(H10), C8(H8), C9(H9), C2(H2)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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 -0.1129(2) 0.1659(3) 0.87674(9) 0.0330(4) Uani 1 1 d . . . . .
F3 F 0.5073(3) 0.2804(3) 0.68536(9) 0.0334(4) Uani 1 1 d . . . . .
F4 F 0.1755(3) 0.1000(2) 0.63422(9) 0.0296(4) Uani 1 1 d . . . . .
F2 F 0.2194(3) 0.3471(2) 0.92774(9) 0.0318(4) Uani 1 1 d . . . . .
O1 O -0.1259(3) 0.0420(3) 0.73164(12) 0.0296(5) Uani 1 1 d . . . . .
O2 O 0.5213(3) 0.4026(3) 0.83140(12) 0.0327(5) Uani 1 1 d . . . . .
C19 C 0.2031(4) 0.2837(4) 0.85745(16) 0.0242(6) Uani 1 1 d . . . . .
C14 C 1.0392(4) 0.6303(4) 0.74110(16) 0.0233(6) Uani 1 1 d . . . . .
C24 C 0.0417(4) 0.1945(4) 0.83255(16) 0.0244(6) Uani 1 1 d . . . . .
C20 C 0.3738(4) 0.3210(4) 0.80836(16) 0.0253(6) Uani 1 1 d . . . . .
C5 C 1.2173(4) 0.6809(4) 0.70386(17) 0.0259(6) Uani 1 1 d . . . . .
C21 C 0.3535(4) 0.2514(4) 0.72998(16) 0.0238(6) Uani 1 1 d . . . . .
C17 C 1.0748(5) 0.5361(4) 0.58707(16) 0.0263(6) Uani 1 1 d . . . . .
C23 C 0.0196(4) 0.1246(4) 0.75375(15) 0.0230(6) Uani 1 1 d . . . . .
C4 C 1.2351(5) 0.6328(4) 0.62245(16) 0.0266(7) Uani 1 1 d . . . . .
C18 C 1.0843(5) 0.4890(4) 0.50987(17) 0.0298(7) Uani 1 1 d . . . . .
H18 H 0.977008 0.423312 0.486496 0.036 Uiso 1 1 calc R U . . .
C13 C 1.0223(4) 0.6751(4) 0.81859(16) 0.0280(6) Uani 1 1 d . . . . .
H13 H 0.904488 0.640869 0.843758 0.034 Uiso 1 1 calc R U . . .
C1 C 1.2431(5) 0.5352(5) 0.46807(17) 0.0365(8) Uani 1 1 d . . . . .
H1 H 1.246621 0.502965 0.415870 0.044 Uiso 1 1 calc R U . . .
C12 C 1.1718(5) 0.7679(4) 0.85975(17) 0.0260(6) Uani 1 1 d . . . . .
C11 C 1.1595(5) 0.8165(4) 0.93830(17) 0.0298(7) Uani 1 1 d . . . . .
H11 H 1.044162 0.784900 0.965557 0.036 Uiso 1 1 calc R U . . .
C22 C 0.1915(4) 0.1617(4) 0.70470(15) 0.0230(6) Uani 1 1 d . . . . .
C3 C 1.3967(5) 0.6787(5) 0.57851(18) 0.0319(7) Uani 1 1 d . . . . .
H3 H 1.505201 0.743999 0.601247 0.038 Uiso 1 1 calc R U . . .
C16 C 0.9000(5) 0.4878(4) 0.62864(19) 0.0321(7) Uani 1 1 d . . . . .
H16 H 0.794848 0.422605 0.603566 0.038 Uiso 1 1 calc R U . . .
C7 C 1.3499(5) 0.8157(4) 0.82109(17) 0.0286(7) Uani 1 1 d . . . . .
C15 C 0.8827(5) 0.5334(4) 0.70238(18) 0.0308(7) Uani 1 1 d . . . . .
H15 H 0.765875 0.500749 0.728545 0.037 Uiso 1 1 calc R U . . .
C6 C 1.3676(4) 0.7717(4) 0.74348(17) 0.0261(7) Uani 1 1 d . . . . .
H6 H 1.485286 0.805161 0.718076 0.031 Uiso 1 1 calc R U . . .
C10 C 1.3107(6) 0.9068(5) 0.97373(17) 0.0339(7) Uani 1 1 d . . . . .
H10 H 1.300587 0.937453 1.025890 0.041 Uiso 1 1 calc R U . . .
C8 C 1.5034(5) 0.9105(5) 0.86116(19) 0.0315(7) Uani 1 1 d . . . . .
H8 H 1.622025 0.942211 0.835939 0.038 Uiso 1 1 calc R U . . .
C9 C 1.4838(5) 0.9567(5) 0.93485(18) 0.0356(8) Uani 1 1 d . . . . .
H9 H 1.586946 1.022997 0.960605 0.043 Uiso 1 1 calc R U . . .
C2 C 1.4036(5) 0.6319(5) 0.50281(18) 0.0359(7) Uani 1 1 d . . . . .
H2 H 1.515920 0.664611 0.474075 0.043 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 C24 1.329(3) . ?
F3 C21 1.330(3) . ?
F4 C22 1.323(3) . ?
F2 C19 1.325(3) . ?
O1 C23 1.204(4) . ?
O2 C20 1.215(4) . ?
C19 C24 1.328(4) . ?
C19 C20 1.479(4) . ?
C14 C5 1.427(4) . ?
C14 C13 1.412(4) . ?
C14 C15 1.425(4) . ?
C24 C23 1.483(4) . ?
C20 C21 1.475(4) . ?
C5 C4 1.485(4) . ?
C5 C6 1.379(4) . ?
C21 C22 1.335(4) . ?
C17 C4 1.417(4) . ?
C17 C18 1.406(4) . ?
C17 C16 1.443(4) . ?
C23 C22 1.484(4) . ?
C4 C3 1.390(4) . ?
C18 H18 0.9500 . ?
C18 C1 1.354(5) . ?
C13 H13 0.9500 . ?
C13 C12 1.396(4) . ?
C1 H1 0.9500 . ?
C1 C2 1.413(5) . ?
C12 C11 1.433(4) . ?
C12 C7 1.434(4) . ?
C11 H11 0.9500 . ?
C11 C10 1.349(5) . ?
C3 H3 0.9500 . ?
C3 C2 1.378(5) . ?
C16 H16 0.9500 . ?
C16 C15 1.349(5) . ?
C7 C6 1.413(4) . ?
C7 C8 1.414(5) . ?
C15 H15 0.9500 . ?
C6 H6 0.9500 . ?
C10 H10 0.9500 . ?
C10 C9 1.412(5) . ?
C8 H8 0.9500 . ?
C8 C9 1.352(5) . ?
C9 H9 0.9500 . ?
C2 H2 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
F2 C19 C24 121.8(3) . . ?
F2 C19 C20 115.9(2) . . ?
C24 C19 C20 122.3(3) . . ?
C13 C14 C5 118.4(3) . . ?
C13 C14 C15 120.1(3) . . ?
C15 C14 C5 121.6(3) . . ?
F1 C24 C23 115.8(2) . . ?
C19 C24 F1 121.6(3) . . ?
C19 C24 C23 122.6(2) . . ?
O2 C20 C19 122.1(3) . . ?
O2 C20 C21 122.4(3) . . ?
C21 C20 C19 115.5(2) . . ?
C14 C5 C4 118.3(3) . . ?
C6 C5 C14 120.1(3) . . ?
C6 C5 C4 121.7(3) . . ?
F3 C21 C20 116.5(2) . . ?
F3 C21 C22 121.2(2) . . ?
C22 C21 C20 122.4(2) . . ?
C4 C17 C16 121.1(3) . . ?
C18 C17 C4 119.6(3) . . ?
C18 C17 C16 119.4(3) . . ?
O1 C23 C24 122.4(2) . . ?
O1 C23 C22 122.6(3) . . ?
C24 C23 C22 115.0(2) . . ?
C17 C4 C5 117.6(3) . . ?
C3 C4 C5 124.4(3) . . ?
C3 C4 C17 118.0(3) . . ?
C17 C18 H18 119.3 . . ?
C1 C18 C17 121.5(3) . . ?
C1 C18 H18 119.3 . . ?
C14 C13 H13 118.7 . . ?
C12 C13 C14 122.6(3) . . ?
C12 C13 H13 118.7 . . ?
C18 C1 H1 120.3 . . ?
C18 C1 C2 119.4(3) . . ?
C2 C1 H1 120.3 . . ?
C13 C12 C11 124.2(3) . . ?
C13 C12 C7 117.8(3) . . ?
C11 C12 C7 118.0(3) . . ?
C12 C11 H11 119.8 . . ?
C10 C11 C12 120.4(3) . . ?
C10 C11 H11 119.8 . . ?
F4 C22 C21 121.7(2) . . ?
F4 C22 C23 116.1(2) . . ?
C21 C22 C23 122.2(2) . . ?
C4 C3 H3 119.1 . . ?
C2 C3 C4 121.7(3) . . ?
C2 C3 H3 119.1 . . ?
C17 C16 H16 119.3 . . ?
C15 C16 C17 121.4(3) . . ?
C15 C16 H16 119.3 . . ?
C6 C7 C12 119.8(3) . . ?
C6 C7 C8 121.0(3) . . ?
C8 C7 C12 119.1(3) . . ?
C14 C15 H15 119.9 . . ?
C16 C15 C14 120.1(3) . . ?
C16 C15 H15 119.9 . . ?
C5 C6 C7 121.3(3) . . ?
C5 C6 H6 119.4 . . ?
C7 C6 H6 119.4 . . ?
C11 C10 H10 119.3 . . ?
C11 C10 C9 121.3(3) . . ?
C9 C10 H10 119.3 . . ?
C7 C8 H8 119.5 . . ?
C9 C8 C7 120.9(3) . . ?
C9 C8 H8 119.5 . . ?
C10 C9 H9 119.9 . . ?
C8 C9 C10 120.3(3) . . ?
C8 C9 H9 119.9 . . ?
C1 C2 H2 120.1 . . ?
C3 C2 C1 119.8(3) . . ?
C3 C2 H2 120.1 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
F1 C24 C23 O1 -2.4(4) . . . . ?
F1 C24 C23 C22 178.6(2) . . . . ?
F3 C21 C22 F4 -0.9(4) . . . . ?
F3 C21 C22 C23 178.8(3) . . . . ?
F2 C19 C24 F1 0.7(5) . . . . ?
F2 C19 C24 C23 179.2(2) . . . . ?
F2 C19 C20 O2 1.0(4) . . . . ?
F2 C19 C20 C21 -179.4(2) . . . . ?
O1 C23 C22 F4 0.7(4) . . . . ?
O1 C23 C22 C21 -179.1(3) . . . . ?
O2 C20 C21 F3 0.8(4) . . . . ?
O2 C20 C21 C22 180.0(3) . . . . ?
C19 C24 C23 O1 179.1(3) . . . . ?
C19 C24 C23 C22 0.0(4) . . . . ?
C19 C20 C21 F3 -178.7(2) . . . . ?
C19 C20 C21 C22 0.5(4) . . . . ?
C14 C5 C4 C17 -1.2(4) . . . . ?
C14 C5 C4 C3 177.8(3) . . . . ?
C14 C5 C6 C7 0.3(4) . . . . ?
C14 C13 C12 C11 179.7(3) . . . . ?
C14 C13 C12 C7 -1.0(4) . . . . ?
C24 C19 C20 O2 -179.9(3) . . . . ?
C24 C19 C20 C21 -0.4(4) . . . . ?
C24 C23 C22 F4 179.7(2) . . . . ?
C24 C23 C22 C21 0.0(4) . . . . ?
C20 C19 C24 F1 -178.3(3) . . . . ?
C20 C19 C24 C23 0.2(4) . . . . ?
C20 C21 C22 F4 -180.0(3) . . . . ?
C20 C21 C22 C23 -0.3(4) . . . . ?
C5 C14 C13 C12 0.5(4) . . . . ?
C5 C14 C15 C16 -0.3(5) . . . . ?
C5 C4 C3 C2 -179.2(3) . . . . ?
C17 C4 C3 C2 -0.3(5) . . . . ?
C17 C18 C1 C2 0.4(5) . . . . ?
C17 C16 C15 C14 -0.4(5) . . . . ?
C4 C5 C6 C7 -179.5(3) . . . . ?
C4 C17 C18 C1 -0.5(5) . . . . ?
C4 C17 C16 C15 0.2(5) . . . . ?
C4 C3 C2 C1 0.2(5) . . . . ?
C18 C17 C4 C5 179.4(3) . . . . ?
C18 C17 C4 C3 0.4(4) . . . . ?
C18 C17 C16 C15 -178.7(3) . . . . ?
C18 C1 C2 C3 -0.2(5) . . . . ?
C13 C14 C5 C4 179.7(2) . . . . ?
C13 C14 C5 C6 -0.1(4) . . . . ?
C13 C14 C15 C16 -178.9(3) . . . . ?
C13 C12 C11 C10 -179.8(3) . . . . ?
C13 C12 C7 C6 1.2(4) . . . . ?
C13 C12 C7 C8 179.7(3) . . . . ?
C12 C11 C10 C9 0.3(5) . . . . ?
C12 C7 C6 C5 -0.8(4) . . . . ?
C12 C7 C8 C9 -0.2(5) . . . . ?
C11 C12 C7 C6 -179.5(3) . . . . ?
C11 C12 C7 C8 -1.0(4) . . . . ?
C11 C10 C9 C8 -1.6(5) . . . . ?
C16 C17 C4 C5 0.6(4) . . . . ?
C16 C17 C4 C3 -178.4(3) . . . . ?
C16 C17 C18 C1 178.4(3) . . . . ?
C7 C12 C11 C10 1.0(5) . . . . ?
C7 C8 C9 C10 1.6(5) . . . . ?
C15 C14 C5 C4 1.1(4) . . . . ?
C15 C14 C5 C6 -178.7(2) . . . . ?
C15 C14 C13 C12 179.2(3) . . . . ?
C6 C5 C4 C17 178.6(3) . . . . ?
C6 C5 C4 C3 -2.4(5) . . . . ?
C6 C7 C8 C9 178.2(3) . . . . ?
C8 C7 C6 C5 -179.3(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 1.493
_oxdiff_exptl_absorpt_empirical_full_min 0.749
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_exp_959_auto
_database_code_depnum_ccdc_archive 'CCDC 2142479'
loop_
_audit_author_name
_audit_author_address
'Peng Hu'
;Northwest University
China
;
_audit_update_record             
;
2022-01-17 deposited with the CCDC.	2022-08-18 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT250_exp_959_auto        
;
PROBLEM: Large U3/U1 Ratio for Average U(i,j) Tensor ....        4.4 Note
RESPONSE: These alerts are generated because there are disorders in the structure
;
# Added during the CSD deposition process: Monday 17 January 2022 03:41 AM
# end Validation Reply Form

_audit_creation_date             2021-08-23
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.07.19 svn.r715e62df for OlexSys, GUI svn.r6383)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        triphenylene-TFBQ
_chemical_formula_moiety         'C6 F4 O2, C18 H12'
_chemical_formula_sum            'C24 H12 F4 O2'
_chemical_formula_weight         408.34
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C F O H'
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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   6.9263(2)
_cell_length_b                   14.1750(4)
_cell_length_c                   17.3722(7)
_cell_angle_alpha                90
_cell_angle_beta                 96.986(3)
_cell_angle_gamma                90
_cell_volume                     1692.95(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    19857
_cell_measurement_temperature    120.01(10)
_cell_measurement_theta_max      77.4370
_cell_measurement_theta_min      4.0000
_shelx_estimated_absorpt_T_max   0.806
_shelx_estimated_absorpt_T_min   0.662
_exptl_absorpt_coefficient_mu    1.126
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.89536
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear reddish'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   reddish
_exptl_crystal_density_diffrn    1.602
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             832
_exptl_crystal_preparation       ?
_exptl_crystal_recrystallization_method 'Slow cooling in acetonitril'
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0334
_diffrn_reflns_av_unetI/netI     0.0133
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            36439
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.248
_diffrn_reflns_theta_min         4.037
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      120.01(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     23.00 102.00   0.50    0.05    --   46.82  77.00 120.00  158
  2  ω     25.00  81.00   0.50    0.05    --   46.82  77.00-120.00  112
  3  ω     35.00  70.00   0.50    0.05    --   46.82  57.00-150.00   70
  4  ω     24.00  67.00   0.50    0.05    --   46.82  77.00-180.00   86
  5  ω     85.00 113.00   0.50    0.05    --   46.82  57.00-150.00   56
  6  ω     53.00  78.00   0.50    0.05    --   46.82  21.00  55.00   50
  7  ω     32.00  63.00   0.50    0.05    --   46.82  57.00 120.00   62
  8  ω     32.00 121.00   0.50    0.05    --   46.82  37.00  90.00  178
  9  ω    107.00 133.00   0.50    0.13    --  108.75 102.00  52.12   52
 10  ω     86.00 135.00   0.50    0.13    --  108.75  81.00  81.19   98
 11  ω     85.00 127.00   0.50    0.13    --  108.75  77.00 120.00   84
 12  ω     91.00 117.00   0.50    0.13    --  108.75  77.00 150.00   52
 13  ω    129.00 178.00   0.50    0.13    --  108.75  77.00 150.00   98
 14  ω    153.00 178.00   0.50    0.13    --  108.75  81.00  81.19   50
 15  ω     93.00 120.00   0.50    0.13    --  108.75  61.00-120.00   54
 16  ω     88.00 137.00   0.50    0.13    --  108.75  77.00-180.00   98
 17  ω     97.00 141.00   0.50    0.13    --  108.75  61.00-180.00   88
 18  ω     92.00 141.00   0.50    0.13    --  108.75  77.00-150.00   98
 19  ω    137.00 178.00   0.50    0.13    --  108.75  61.00   0.00   82
 20  ω    147.00 173.00   0.50    0.13    --  108.75  61.00  60.00   52
 21  ω     91.00 120.00   0.50    0.13    --  108.75  61.00 150.00   58
 22  ω     93.00 119.00   0.50    0.13    --  108.75  61.00 120.00   52
 23  ω     96.00 122.00   0.50    0.13    --  108.75  61.00  90.00   52
 24  ω     91.00 127.00   0.50    0.13    --  108.75  61.00-150.00   72
 25  ω    133.00 177.00   0.50    0.13    --  108.75  61.00-150.00   88
 26  ω    151.00 178.00   0.50    0.13    --  108.75  61.00-180.00   54
 27  ω    152.00 177.00   0.50    0.13    --  108.75  61.00-120.00   50
 28  ω    144.00 175.00   0.50    0.13    --  108.75  45.00 -90.00   62
 29  ω    127.00 153.00   0.50    0.13    --  108.75  45.00 -60.00   52
 30  ω     96.00 123.00   0.50    0.13    --  108.75  45.00 -90.00   54
 31  ω    103.00 132.00   0.50    0.13    --  108.75  45.00-180.00   58
 32  ω    127.00 170.00   0.50    0.13    --  108.75  45.00-120.00   86
 33  ω    148.00 174.00   0.50    0.13    --  108.75  30.00 -30.00   52
 34  ω    104.00 136.00   0.50    0.13    --  108.75  30.00 -30.00   64
 35  ω     94.00 123.00   0.50    0.13    --  108.75  30.00   0.00   58
 36  ω    138.00 173.00   0.50    0.13    --  108.75  30.00   0.00   70
 37  ω    144.00 178.00   0.50    0.13    --  108.75  35.00  80.12   68
 38  ω    110.00 176.00   0.50    0.13    --  108.75  15.00 150.00  132
 39  ω     99.00 146.00   0.50    0.13    --  108.75  30.00 150.00   94
 40  ω     94.00 129.00   0.50    0.13    --  108.75  35.00  80.12   70
 41  ω    117.00 171.00   0.50    0.13    --  108.75  21.00  55.00  108
 42  ω     96.00 178.00   0.50    0.13    --  108.75  15.00-180.00  164
 43  ω     36.00 106.00   0.50    0.13    --  108.75 -77.00  60.00  140
 44  ω     41.00  67.00   0.50    0.13    --  108.75 -61.00 120.00   52
 45  ω     46.00  91.00   0.50    0.13    --  108.75 -77.00   0.00   90
 46  ω     59.00  85.00   0.50    0.13    --  108.75 -77.00 -60.00   52
 47  ω     74.00 100.00   0.50    0.13    --  108.75 -77.00-180.00   52
 48  ω     37.00  75.00   0.50    0.13    --  108.75 -61.00 -60.00   76
 49  ω    -23.00   3.00   0.50    0.05    --   46.82 -21.00-110.00   52
 50  ω    -24.00  28.00   0.50    0.05    --   46.82 -19.00 120.00  104
 51  ω     36.00  70.00   0.50    0.13    --  108.75 -61.00 150.00   68
 52  ω     37.00  63.00   0.50    0.13    --  108.75 -61.00  90.00   52
 53  ω     45.00  73.00   0.50    0.13    --  108.75 -61.00  60.00   56
 54  ω     40.00 115.00   0.50    0.13    --  108.75 -86.00  49.72  150
 55  ω     20.00  94.00   0.50    0.05    --   46.82-125.00  60.00  148
 56  ω     82.00 110.00   0.50    0.13    --  108.75-125.00 -30.00   56
 57  ω     57.00  83.00   0.50    0.13    --  108.75-125.00 -90.00   52
 58  ω     41.00  74.00   0.50    0.13    --  108.75-125.00 -30.00   66
 59  ω     36.00  91.00   0.50    0.13    --  108.75 -94.00 -90.00  110
 60  ω     37.00  97.00   0.50    0.13    --  108.75-125.00   0.00  120
 61  ω     65.00 105.00   0.50    0.13    --  108.75 -94.00 120.00   80
 62  ω     59.00 105.00   0.50    0.13    --  108.75 -94.00 150.00   92
 63  ω     60.00 104.00   0.50    0.13    --  108.75 -94.00  30.00   88
 64  ω     72.00 105.00   0.50    0.13    --  108.75 -93.00   6.64   66
 65  ω     52.00  78.00   0.50    0.13    --  108.75 -94.00-120.00   52
 66  ω     52.00  78.00   0.50    0.13    --  108.75 -94.00-180.00   52
 67  ω   -102.00 -67.00   0.50    0.05    --  -46.82 -21.00-110.00   70
 68  ω    -68.00 -43.00   0.50    0.13    --  -99.00  61.00-150.00   50
 69  ω   -102.00 -76.00   0.50    0.13    --  -99.00 -77.00-180.00   52
 70  ω   -101.00 -76.00   0.50    0.13    --  -99.00 -77.00-150.00   50
 71  ω   -100.00 -75.00   0.50    0.13    --  -99.00 -76.00-145.55   50
 72  ω   -100.00 -75.00   0.50    0.13    --  -99.00 -76.00-165.05   50
 73  ω   -108.00 -76.00   0.50    0.13    --  -99.00 -76.00  98.39   64
 74  ω   -103.00 -77.00   0.50    0.13    --  -99.00 -74.00 162.31   52
 75  ω   -101.00 -75.00   0.50    0.13    --  -99.00 -77.00 150.00   52
 76  ω   -103.00 -77.00   0.50    0.13    --  -99.00 -73.00 153.02   52
 77  ω   -103.00 -77.00   0.50    0.13    --  -99.00 -74.00 140.34   52
 78  ω   -102.00 -77.00   0.50    0.13    --  -99.00 -73.00 157.69   50
 79  ω   -103.00 -77.00   0.50    0.13    --  -99.00 -77.00 120.00   52
 80  ω   -104.00 -78.00   0.50    0.13    --  -99.00 -72.00 121.03   52
 81  ω   -110.00 -78.00   0.50    0.13    --  -99.00 -70.00  98.61   64
 82  ω   -104.00 -78.00   0.50    0.13    --  -99.00 -69.00 126.15   52
 83  ω   -103.00 -78.00   0.50    0.13    --  -99.00 -70.00-133.89   50
 84  ω   -107.00 -81.00   0.50    0.13    --  -99.00 -68.00-166.82   52
 85  ω   -102.00 -77.00   0.50    0.13    --  -99.00 -72.00-169.25   50
 86  ω   -108.00 -82.00   0.50    0.13    --  -99.00 -66.00-147.69   52
 87  ω    -16.00  20.00   0.50    0.05    --  -46.82  21.00  55.00   72
 88  ω   -109.00 -80.00   0.50    0.13    --  -99.00 -67.00 102.50   58
 89  ω   -120.00 -79.00   0.50    0.13    --  -99.00 -67.00 140.50   82
 90  ω   -107.00 -81.00   0.50    0.13    --  -99.00 -63.00 171.03   52
 91  ω   -107.00 -81.00   0.50    0.13    --  -99.00 -61.00 150.00   52
 92  ω   -107.00 -81.00   0.50    0.13    --  -99.00 -61.00 120.00   52
 93  ω   -167.00-124.00   0.50    0.13    --  -99.00 -67.00 140.50   86
 94  ω   -153.00-128.00   0.50    0.13    --  -99.00 -21.00-110.00   50
 95  ω   -107.00 -81.00   0.50    0.13    --  -99.00 -61.00-150.00   52
 96  ω   -109.00 -84.00   0.50    0.13    --  -99.00 -45.00-150.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1979131000
_diffrn_orient_matrix_UB_12      -0.0272497000
_diffrn_orient_matrix_UB_13      0.0253752000
_diffrn_orient_matrix_UB_21      0.0838394000
_diffrn_orient_matrix_UB_22      0.0143183000
_diffrn_orient_matrix_UB_23      0.0855074000
_diffrn_orient_matrix_UB_31      -0.0632330000
_diffrn_orient_matrix_UB_32      0.1042781000
_diffrn_orient_matrix_UB_33      -0.0052262000
_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              'PhotonJet R (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2793
_reflns_number_total             3087
_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 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    
;
Superflip  (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.441
_refine_diff_density_min         -0.611
_refine_diff_density_rms         0.069
_refine_ls_extinction_coef       0.0020(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.169
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     272
_refine_ls_number_reflns         3087
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0941
_refine_ls_R_factor_gt           0.0888
_refine_ls_restrained_S_all      1.174
_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)+(0.0658P)²+5.1673P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2312
_refine_ls_wR_factor_ref         0.2341
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Rigid bond restraints
 F13, C76
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.001
 C17, C73
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.001
 C17, C91
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.001
 C47, C76
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.001
 C47, C90
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.001
 O9, C73
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.001
3.a Aromatic/amide H refined with riding coordinates:
 C19(H19), C23(H23), C28(H28), C33(H33), C49(H49), C52(H52), C56(H56),
 C65(H65), C71(H71), C77(H77), C81(H81), C95(H95)
;
_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
F4 F 0.3627(3) 0.93936(15) 0.42783(17) 0.0510(8) Uani 1 1 d . . . . .
F5 F 0.6249(4) 0.57302(16) 0.4382(2) 0.0664(10) Uani 1 1 d . . . . .
O9 O 0.4285(4) 0.84729(17) 0.29773(19) 0.0402(7) Uani 1 1 d . U . . .
F13 F 0.5730(4) 0.66846(18) 0.2985(2) 0.0704(10) Uani 1 1 d . U . . .
F16 F 0.4225(4) 0.8444(2) 0.56360(19) 0.0610(8) Uani 1 1 d . . . . .
O21 O 0.5415(5) 0.6622(2) 0.5711(3) 0.0687(12) Uani 1 1 d . . . . .
C1 C 0.0807(5) 0.1478(2) 0.6079(3) 0.0397(11) Uani 1 1 d . . . . .
C6 C -0.0637(5) 0.3383(2) 0.5983(3) 0.0354(10) Uani 1 1 d . . . . .
C14 C -0.0358(5) 0.2920(2) 0.6707(3) 0.0351(10) Uani 1 1 d . . . . .
C17 C 0.4246(5) 0.8502(3) 0.4306(3) 0.0474(10) Uani 1 1 d . U . . .
C19 C -0.1349(5) 0.4320(2) 0.5960(3) 0.0372(10) Uani 1 1 d . . . . .
H19 H -0.153972 0.464119 0.547698 0.045 Uiso 1 1 calc R U . . .
C23 C 0.1539(5) 0.0543(3) 0.6145(3) 0.0485(13) Uani 1 1 d . . . . .
H23 H 0.182896 0.022341 0.569263 0.058 Uiso 1 1 calc R U . . .
C26 C -0.0218(5) 0.2895(2) 0.5283(3) 0.0346(9) Uani 1 1 d . . . . .
C28 C -0.0795(5) 0.3403(3) 0.7369(3) 0.0421(10) Uani 1 1 d . . . . .
H28 H -0.060797 0.309615 0.785851 0.050 Uiso 1 1 calc R U . . .
C29 C 0.0493(5) 0.1952(3) 0.5329(3) 0.0397(11) Uani 1 1 d . . . . .
C33 C -0.1771(5) 0.4775(3) 0.6612(3) 0.0394(10) Uani 1 1 d . . . . .
H33 H -0.225273 0.540283 0.657877 0.047 Uiso 1 1 calc R U . . .
C41 C 0.0388(5) 0.1945(3) 0.6756(3) 0.0385(10) Uani 1 1 d . . . . .
C47 C 0.5611(6) 0.6616(3) 0.4343(4) 0.0609(12) Uani 1 1 d . U . . .
C49 C 0.1836(6) 0.0094(3) 0.6844(3) 0.0553(15) Uani 1 1 d . . . . .
H49 H 0.232631 -0.053301 0.687457 0.066 Uiso 1 1 calc R U . . .
C52 C -0.1495(6) 0.4320(3) 0.7321(3) 0.0425(11) Uani 1 1 d . . . . .
H52 H -0.178459 0.463584 0.777572 0.051 Uiso 1 1 calc R U . . .
C56 C -0.0513(5) 0.3327(3) 0.4545(3) 0.0436(11) Uani 1 1 d . . . . .
H56 H -0.100163 0.395327 0.450562 0.052 Uiso 1 1 calc R U . . .
C65 C 0.1421(7) 0.0553(3) 0.7507(4) 0.0581(15) Uani 1 1 d . . . . .
H65 H 0.163149 0.024011 0.799403 0.070 Uiso 1 1 calc R U . . .
C71 C 0.0876(6) 0.1506(3) 0.4638(3) 0.0487(12) Uani 1 1 d . . . . .
H71 H 0.135431 0.087750 0.466222 0.058 Uiso 1 1 calc R U . . .
C73 C 0.4593(6) 0.8057(3) 0.3609(3) 0.0479(10) Uani 1 1 d . U . . .
C76 C 0.5343(6) 0.7076(3) 0.3636(4) 0.0544(10) Uani 1 1 d . U . . .
C77 C 0.0698(6) 0.1469(3) 0.7466(3) 0.0509(13) Uani 1 1 d . . . . .
H77 H 0.041194 0.177487 0.792518 0.061 Uiso 1 1 calc R U . . .
C81 C -0.0119(6) 0.2873(3) 0.3883(3) 0.0490(12) Uani 1 1 d . . . . .
H81 H -0.032169 0.318677 0.339668 0.059 Uiso 1 1 calc R U . . .
C90 C 0.5222(6) 0.7047(3) 0.5049(4) 0.0571(13) Uani 1 1 d . U . . .
C91 C 0.4544(6) 0.8037(3) 0.5002(4) 0.0542(12) Uani 1 1 d . U . . .
C95 C 0.0579(6) 0.1952(3) 0.3930(3) 0.0535(13) Uani 1 1 d . . . . .
H95 H 0.084906 0.163247 0.347465 0.064 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
F4 C17 1.333(4) . ?
F5 C47 1.330(5) . ?
O9 C73 1.241(5) . ?
F13 C76 1.316(7) . ?
F16 C91 1.286(6) . ?
O21 C90 1.291(7) . ?
C1 C23 1.418(5) . ?
C1 C29 1.459(7) . ?
C1 C41 1.411(6) . ?
C6 C14 1.410(6) . ?
C6 C19 1.416(5) . ?
C6 C26 1.459(6) . ?
C14 C28 1.402(6) . ?
C14 C41 1.475(5) . ?
C17 C73 1.413(7) . ?
C17 C91 1.370(7) . ?
C19 H19 0.9500 . ?
C19 C33 1.366(6) . ?
C23 H23 0.9500 . ?
C23 C49 1.364(7) . ?
C26 C29 1.423(5) . ?
C26 C56 1.413(6) . ?
C28 H28 0.9500 . ?
C28 C52 1.386(6) . ?
C29 C71 1.410(7) . ?
C33 H33 0.9500 . ?
C33 C52 1.383(6) . ?
C41 C77 1.399(7) . ?
C47 C76 1.383(8) . ?
C47 C90 1.424(8) . ?
C49 H49 0.9500 . ?
C49 C65 1.384(8) . ?
C52 H52 0.9500 . ?
C56 H56 0.9500 . ?
C56 C81 1.374(7) . ?
C65 H65 0.9500 . ?
C65 C77 1.390(6) . ?
C71 H71 0.9500 . ?
C71 C95 1.376(7) . ?
C73 C76 1.484(5) . ?
C77 H77 0.9500 . ?
C81 H81 0.9500 . ?
C81 C95 1.391(7) . ?
C90 C91 1.479(6) . ?
C95 H95 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
C23 C1 C29 121.1(4) . . ?
C41 C1 C23 118.6(4) . . ?
C41 C1 C29 120.4(3) . . ?
C14 C6 C19 118.1(4) . . ?
C14 C6 C26 120.2(3) . . ?
C19 C6 C26 121.7(4) . . ?
C6 C14 C41 119.8(4) . . ?
C28 C14 C6 119.0(3) . . ?
C28 C14 C41 121.3(4) . . ?
F4 C17 C73 118.7(4) . . ?
F4 C17 C91 120.1(5) . . ?
C91 C17 C73 121.2(4) . . ?
C6 C19 H19 119.1 . . ?
C33 C19 C6 121.9(4) . . ?
C33 C19 H19 119.1 . . ?
C1 C23 H23 119.2 . . ?
C49 C23 C1 121.5(5) . . ?
C49 C23 H23 119.2 . . ?
C29 C26 C6 120.1(4) . . ?
C56 C26 C6 122.0(3) . . ?
C56 C26 C29 117.9(4) . . ?
C14 C28 H28 119.4 . . ?
C52 C28 C14 121.2(4) . . ?
C52 C28 H28 119.4 . . ?
C26 C29 C1 119.7(4) . . ?
C71 C29 C1 122.0(4) . . ?
C71 C29 C26 118.3(4) . . ?
C19 C33 H33 120.1 . . ?
C19 C33 C52 119.9(4) . . ?
C52 C33 H33 120.1 . . ?
C1 C41 C14 119.8(4) . . ?
C77 C41 C1 118.9(4) . . ?
C77 C41 C14 121.2(4) . . ?
F5 C47 C76 119.8(5) . . ?
F5 C47 C90 117.3(5) . . ?
C76 C47 C90 122.9(4) . . ?
C23 C49 H49 120.1 . . ?
C23 C49 C65 119.8(4) . . ?
C65 C49 H49 120.1 . . ?
C28 C52 H52 120.0 . . ?
C33 C52 C28 120.0(4) . . ?
C33 C52 H52 120.0 . . ?
C26 C56 H56 118.8 . . ?
C81 C56 C26 122.4(4) . . ?
C81 C56 H56 118.8 . . ?
C49 C65 H65 119.8 . . ?
C49 C65 C77 120.4(5) . . ?
C77 C65 H65 119.8 . . ?
C29 C71 H71 118.9 . . ?
C95 C71 C29 122.1(4) . . ?
C95 C71 H71 118.9 . . ?
O9 C73 C17 121.2(4) . . ?
O9 C73 C76 119.7(5) . . ?
C17 C73 C76 119.1(5) . . ?
F13 C76 C47 123.1(4) . . ?
F13 C76 C73 118.3(5) . . ?
C47 C76 C73 118.6(5) . . ?
C41 C77 H77 119.6 . . ?
C65 C77 C41 120.8(5) . . ?
C65 C77 H77 119.6 . . ?
C56 C81 H81 120.2 . . ?
C56 C81 C95 119.5(5) . . ?
C95 C81 H81 120.2 . . ?
O21 C90 C47 123.8(4) . . ?
O21 C90 C91 119.3(5) . . ?
C47 C90 C91 116.9(5) . . ?
F16 C91 C17 121.1(4) . . ?
F16 C91 C90 117.7(5) . . ?
C17 C91 C90 121.2(5) . . ?
C71 C95 C81 119.8(5) . . ?
C71 C95 H95 120.1 . . ?
C81 C95 H95 120.1 . . ?

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
F4 C17 C73 O9 -1.8(5) . . . . ?
F4 C17 C73 C76 178.1(3) . . . . ?
F4 C17 C91 F16 0.4(6) . . . . ?
F4 C17 C91 C90 179.7(3) . . . . ?
F5 C47 C76 F13 -1.5(6) . . . . ?
F5 C47 C76 C73 178.8(3) . . . . ?
F5 C47 C90 O21 -1.5(6) . . . . ?
F5 C47 C90 C91 179.0(3) . . . . ?
O9 C73 C76 F13 2.5(5) . . . . ?
O9 C73 C76 C47 -177.8(4) . . . . ?
O21 C90 C91 F16 1.9(6) . . . . ?
O21 C90 C91 C17 -177.4(4) . . . . ?
C1 C23 C49 C65 -0.1(6) . . . . ?
C1 C29 C71 C95 179.9(3) . . . . ?
C1 C41 C77 C65 0.5(6) . . . . ?
C6 C14 C28 C52 0.1(5) . . . . ?
C6 C14 C41 C1 -0.4(5) . . . . ?
C6 C14 C41 C77 179.4(3) . . . . ?
C6 C19 C33 C52 0.3(5) . . . . ?
C6 C26 C29 C1 -0.2(5) . . . . ?
C6 C26 C29 C71 179.9(3) . . . . ?
C6 C26 C56 C81 179.9(3) . . . . ?
C14 C6 C19 C33 -0.2(5) . . . . ?
C14 C6 C26 C29 -0.6(5) . . . . ?
C14 C6 C26 C56 178.8(3) . . . . ?
C14 C28 C52 C33 -0.1(6) . . . . ?
C14 C41 C77 C65 -179.3(4) . . . . ?
C17 C73 C76 F13 -177.4(3) . . . . ?
C17 C73 C76 C47 2.3(5) . . . . ?
C19 C6 C14 C28 0.0(5) . . . . ?
C19 C6 C14 C41 -179.8(3) . . . . ?
C19 C6 C26 C29 -179.9(3) . . . . ?
C19 C6 C26 C56 -0.5(5) . . . . ?
C19 C33 C52 C28 -0.1(6) . . . . ?
C23 C1 C29 C26 -179.1(3) . . . . ?
C23 C1 C29 C71 0.7(5) . . . . ?
C23 C1 C41 C14 179.4(3) . . . . ?
C23 C1 C41 C77 -0.4(5) . . . . ?
C23 C49 C65 C77 0.2(6) . . . . ?
C26 C6 C14 C28 -179.2(3) . . . . ?
C26 C6 C14 C41 0.9(5) . . . . ?
C26 C6 C19 C33 179.0(3) . . . . ?
C26 C29 C71 C95 -0.2(5) . . . . ?
C26 C56 C81 C95 0.6(6) . . . . ?
C28 C14 C41 C1 179.8(3) . . . . ?
C28 C14 C41 C77 -0.4(5) . . . . ?
C29 C1 C23 C49 -179.9(3) . . . . ?
C29 C1 C41 C14 -0.4(5) . . . . ?
C29 C1 C41 C77 179.7(3) . . . . ?
C29 C26 C56 C81 -0.7(5) . . . . ?
C29 C71 C95 C81 0.1(6) . . . . ?
C41 C1 C23 C49 0.2(5) . . . . ?
C41 C1 C29 C26 0.8(5) . . . . ?
C41 C1 C29 C71 -179.4(3) . . . . ?
C41 C14 C28 C52 180.0(3) . . . . ?
C47 C90 C91 F16 -178.5(4) . . . . ?
C47 C90 C91 C17 2.1(6) . . . . ?
C49 C65 C77 C41 -0.4(6) . . . . ?
C56 C26 C29 C1 -179.6(3) . . . . ?
C56 C26 C29 C71 0.5(5) . . . . ?
C56 C81 C95 C71 -0.3(6) . . . . ?
C73 C17 C91 F16 -179.9(3) . . . . ?
C73 C17 C91 C90 -0.6(6) . . . . ?
C76 C47 C90 O21 178.2(4) . . . . ?
C76 C47 C90 C91 -1.3(6) . . . . ?
C90 C47 C76 F13 178.9(4) . . . . ?
C90 C47 C76 C73 -0.8(6) . . . . ?
C91 C17 C73 O9 178.5(3) . . . . ?
C91 C17 C73 C76 -1.6(6) . . . . ?

_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2

_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 1.245
_oxdiff_exptl_absorpt_empirical_full_min 0.844
