# Electronic Supplementary Material (ESI) for Chemical Science.
# 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_zhuwr_210323
_database_code_depnum_ccdc_archive 'CCDC 2101620'
loop_
_audit_author_name
_audit_author_address
'Frank Allen'
;The Cambridge Crystallographic Data Center
China
;
_audit_update_record             
;
2021-08-05 deposited with the CCDC.	2021-11-19 downloaded from the CCDC.
;
_audit_creation_date             2021-03-24
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H17 F3 N2 O'
_chemical_formula_sum            'C22 H17 F3 N2 O'
_chemical_formula_weight         382.37
_chemical_absolute_configuration ad
_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'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      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                   9.40350(10)
_cell_length_b                   10.62490(10)
_cell_length_c                   9.51730(10)
_cell_angle_alpha                90
_cell_angle_beta                 95.3790(10)
_cell_angle_gamma                90
_cell_volume                     946.698(17)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    16928
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      76.7630
_cell_measurement_theta_min      4.6680
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.873
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.86976
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
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    1.341
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             396
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0419
_diffrn_reflns_av_unetI/netI     0.0295
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            19789
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.763
_diffrn_reflns_theta_min         4.667
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.993
_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  72.00   0.50    0.08    --   46.37  77.00 -90.00   98
  2  ω     23.00 118.00   0.50    0.08    --   46.37  77.00   0.00  190
  3  ω     30.00 118.00   0.50    0.08    --   46.37  57.00 120.00  176
  4  ω     79.00 178.00   0.50    0.50    --  107.00 125.00  60.00  198
  5  ω     79.00 178.00   0.50    0.50    --  107.00 125.00  30.00  198
  6  ω     89.00 178.00   0.50    0.50    --  107.00 105.00 -33.00  178
  7  ω     93.00 178.00   0.50    0.50    --  107.00  45.00  60.00  170
  8  ω     93.00 178.00   0.50    0.50    --  107.00  45.00  30.00  170
  9  ω     93.00 178.00   0.50    0.50    --  107.00  45.00-180.00  170
 10  ω    -27.00  45.00   0.50    0.08    --   46.37 -38.00 -30.00  144
 11  ω     34.00 107.00   0.50    0.50    --  107.00 -77.00  90.00  146
 12  ω     34.00  73.00   0.50    0.50    --  107.00 -61.00  30.00   78
 13  ω     34.00  73.00   0.50    0.50    --  107.00 -61.00   0.00   78
 14  ω     34.00 106.00   0.50    0.50    --  107.00 -94.00 -90.00  144
 15  ω     34.00 112.00   0.50    0.50    --  107.00-125.00-150.00  156
 16  ω     34.00 112.00   0.50    0.50    --  107.00-125.00-180.00  156
 17  ω     18.00  95.00   0.50    0.08    --   46.37-125.00-120.00  154
 18  ω     34.00 112.00   0.50    0.50    --  107.00-125.00 -30.00  156
 19  ω     34.00 112.00   0.50    0.50    --  107.00-125.00   0.00  156
 20  ω     34.00 112.00   0.50    0.50    --  107.00-125.00  30.00  156
 21  ω     34.00 112.00   0.50    0.50    --  107.00-125.00  60.00  156
 22  ω     34.00 112.00   0.50    0.50    --  107.00-125.00 120.00  156
 23  ω     34.00 112.00   0.50    0.50    --  107.00-125.00 150.00  156
 24  ω     34.00 107.00   0.50    0.50    --  107.00-105.00-133.00  146
 25  ω     34.00 106.00   0.50    0.50    --  107.00 -94.00-120.00  144
 26  ω      2.00  84.00   0.50    0.08    --   46.37-105.00-133.00  164
 27  ω   -173.00 -84.00   0.50    0.50    -- -100.00 -55.00 139.42  178
 28  ω   -118.00 -23.00   0.50    0.08    --  -46.37 -77.00-180.00  190
 29  ω   -173.00 -76.00   0.50    0.50    -- -100.00 -77.00-180.00  194
 30  ω   -107.00 -27.00   0.50    0.50    -- -100.00 105.00 -33.00  160
 31  ω    -84.00   2.00   0.50    0.08    --  -46.37 105.00 -33.00  172
 32  ω   -173.00 -79.00   0.50    0.50    -- -100.00 -69.00 -30.26  188
 33  ω   -173.00 -77.00   0.50    0.50    -- -100.00 -75.00-111.07  192
 34  ω   -173.00 -84.00   0.50    0.50    -- -100.00-105.00-133.00  178
 35  ω    -69.00 -27.00   0.50    0.50    -- -100.00  61.00-180.00   84
 36  ω    -69.00 -27.00   0.50    0.50    -- -100.00  61.00 -90.00   84
 37  ω   -103.00 -27.00   0.50    0.50    -- -100.00  77.00  90.00  152
 38  ω    -69.00 -27.00   0.50    0.50    -- -100.00  61.00 150.00   84
 39  ω    -41.00  27.00   0.50    0.08    --  -46.37  38.00 150.00  136
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0291489000
_diffrn_orient_matrix_UB_12      -0.0164824000
_diffrn_orient_matrix_UB_13      -0.1555687000
_diffrn_orient_matrix_UB_21      -0.0397695000
_diffrn_orient_matrix_UB_22      0.1388824000
_diffrn_orient_matrix_UB_23      -0.0287236000
_diffrn_orient_matrix_UB_31      0.1569777000
_diffrn_orient_matrix_UB_32      0.0382329000
_diffrn_orient_matrix_UB_33      0.0376165000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.875
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.971
_reflns_number_gt                3823
_reflns_number_total             3896
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     71.98
_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 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.214
_refine_diff_density_min         -0.188
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details 
;
 Flack x determined using 1744 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.01(4)
_refine_ls_extinction_coef       0.0039(7)
_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   1.072
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     256
_refine_ls_number_reflns         3896
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0307
_refine_ls_R_factor_gt           0.0302
_refine_ls_restrained_S_all      1.072
_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)+(0.0389P)²+0.1569P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0767
_refine_ls_wR_factor_ref         0.0771
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N13(H13), C11(H11), C5(H5), C17(H17), C8(H8), C7(H7), C14(H14), C12(H12),
 C20(H20), C18(H18), C19(H19)
2.b Idealised Me refined as rotating group:
 C27(H27A,H27B,H27C), C28(H28A,H28B,H28C)
;
_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
F23 F 0.91160(13) 0.61217(14) 0.24430(13) 0.0352(3) Uani 1 1 d . . . . .
F24 F 0.97860(13) 0.44383(13) 0.35676(13) 0.0345(3) Uani 1 1 d . . . . .
F25 F 1.06491(13) 0.62418(15) 0.42640(14) 0.0393(3) Uani 1 1 d . . . . .
O26 O 0.14331(15) 0.38962(13) 0.07115(15) 0.0274(3) Uani 1 1 d . . . . .
N1 N 0.59800(17) 0.63134(15) 0.35435(17) 0.0231(3) Uani 1 1 d . . . . .
N13 N 0.97587(19) 0.45954(17) 0.81569(18) 0.0297(4) Uani 1 1 d . . . . .
H13 H 1.044456 0.436175 0.876200 0.036 Uiso 1 1 calc R U . . .
C2 C 0.68652(19) 0.53074(18) 0.39239(19) 0.0206(4) Uani 1 1 d . . . . .
C16 C 0.7568(2) 0.50527(18) 0.7130(2) 0.0234(4) Uani 1 1 d . . . . .
C9 C 0.4718(2) 0.58741(18) 0.2870(2) 0.0219(4) Uani 1 1 d . . . . .
C21 C 0.8344(2) 0.46332(19) 0.8389(2) 0.0274(4) Uani 1 1 d . . . . .
C11 C 0.7868(2) 0.72349(19) 0.4722(2) 0.0270(4) Uani 1 1 d . . . . .
H11 H 0.846208 0.785203 0.514866 0.032 Uiso 1 1 calc R U . . .
C5 C 0.3713(2) 0.38338(19) 0.21605(19) 0.0220(4) Uani 1 1 d . . . . .
H5 H 0.374719 0.295900 0.215710 0.026 Uiso 1 1 calc R U . . .
C4 C 0.48252(19) 0.45500(17) 0.28592(18) 0.0201(4) Uani 1 1 d . . . . .
C3 C 0.62077(19) 0.41969(18) 0.35432(19) 0.0214(4) Uani 1 1 d . . . . .
C22 C 0.9452(2) 0.5655(2) 0.3735(2) 0.0284(4) Uani 1 1 d . . . . .
C17 C 0.6083(2) 0.5220(2) 0.7115(2) 0.0264(4) Uani 1 1 d . . . . .
H17 H 0.554411 0.548949 0.630134 0.032 Uiso 1 1 calc R U . . .
C15 C 0.85969(19) 0.52732(19) 0.61331(19) 0.0222(4) Uani 1 1 d . . . . .
C8 C 0.3544(2) 0.65119(19) 0.2208(2) 0.0259(4) Uani 1 1 d . . . . .
H8 H 0.348167 0.738488 0.223681 0.031 Uiso 1 1 calc R U . . .
C7 C 0.2480(2) 0.57948(19) 0.1509(2) 0.0255(4) Uani 1 1 d . . . . .
H7 H 0.168764 0.619167 0.104638 0.031 Uiso 1 1 calc R U . . .
C6 C 0.25704(19) 0.44739(19) 0.14815(19) 0.0223(4) Uani 1 1 d . . . . .
C14 C 0.9908(2) 0.49876(19) 0.6812(2) 0.0269(4) Uani 1 1 d . . . . .
H14 H 1.077172 0.505152 0.641549 0.032 Uiso 1 1 calc R U . . .
C10 C 0.8239(2) 0.58258(18) 0.4680(2) 0.0227(4) Uani 1 1 d . . . . .
C27 C 0.1380(2) 0.2555(2) 0.0784(2) 0.0327(5) Uani 1 1 d . . . . .
H27A H 0.054649 0.225598 0.022321 0.049 Uiso 1 1 calc R U . . .
H27B H 0.133845 0.229904 0.174708 0.049 Uiso 1 1 calc R U . . .
H27C H 0.221918 0.220704 0.043149 0.049 Uiso 1 1 calc R U . . .
C12 C 0.6582(2) 0.74484(19) 0.4066(2) 0.0277(4) Uani 1 1 d . . . . .
H12 H 0.614577 0.823292 0.396694 0.033 Uiso 1 1 calc R U . . .
C28 C 0.6770(2) 0.28884(19) 0.3762(2) 0.0297(4) Uani 1 1 d . . . . .
H28A H 0.689309 0.251291 0.286350 0.044 Uiso 1 1 calc R U . . .
H28B H 0.610515 0.239764 0.423824 0.044 Uiso 1 1 calc R U . . .
H28C H 0.767242 0.291430 0.432303 0.044 Uiso 1 1 calc R U . . .
C20 C 0.7691(3) 0.4378(2) 0.9618(2) 0.0338(5) Uani 1 1 d . . . . .
H20 H 0.821546 0.409781 1.043530 0.041 Uiso 1 1 calc R U . . .
C18 C 0.5441(3) 0.4976(2) 0.8331(2) 0.0351(5) Uani 1 1 d . . . . .
H18 H 0.446057 0.508942 0.833344 0.042 Uiso 1 1 calc R U . . .
C19 C 0.6238(3) 0.4559(2) 0.9567(2) 0.0385(5) Uani 1 1 d . . . . .
H19 H 0.577181 0.440116 1.036849 0.046 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
F23 C22 1.336(2) . ?
F24 C22 1.343(3) . ?
F25 C22 1.343(2) . ?
O26 C6 1.382(2) . ?
O26 C27 1.428(2) . ?
N1 C2 1.382(2) . ?
N1 C9 1.377(2) . ?
N1 C12 1.403(3) . ?
N13 H13 0.8600 . ?
N13 C21 1.369(3) . ?
N13 C14 1.365(3) . ?
C2 C3 1.365(3) . ?
C2 C10 1.522(2) . ?
C16 C21 1.415(3) . ?
C16 C17 1.407(3) . ?
C16 C15 1.436(3) . ?
C9 C4 1.411(3) . ?
C9 C8 1.394(3) . ?
C21 C20 1.398(3) . ?
C11 H11 0.9300 . ?
C11 C10 1.539(3) . ?
C11 C12 1.327(3) . ?
C5 H5 0.9300 . ?
C5 C4 1.409(3) . ?
C5 C6 1.380(3) . ?
C4 C3 1.448(3) . ?
C3 C28 1.495(3) . ?
C22 C10 1.528(3) . ?
C17 H17 0.9300 . ?
C17 C18 1.379(3) . ?
C15 C14 1.371(3) . ?
C15 C10 1.511(3) . ?
C8 H8 0.9300 . ?
C8 C7 1.378(3) . ?
C7 H7 0.9300 . ?
C7 C6 1.406(3) . ?
C14 H14 0.9300 . ?
C27 H27A 0.9600 . ?
C27 H27B 0.9600 . ?
C27 H27C 0.9600 . ?
C12 H12 0.9300 . ?
C28 H28A 0.9600 . ?
C28 H28B 0.9600 . ?
C28 H28C 0.9600 . ?
C20 H20 0.9300 . ?
C20 C19 1.376(4) . ?
C18 H18 0.9300 . ?
C18 C19 1.406(4) . ?
C19 H19 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
C6 O26 C27 116.50(15) . . ?
C2 N1 C12 111.02(16) . . ?
C9 N1 C2 109.37(16) . . ?
C9 N1 C12 139.29(17) . . ?
C21 N13 H13 125.4 . . ?
C14 N13 H13 125.4 . . ?
C14 N13 C21 109.21(16) . . ?
N1 C2 C10 107.92(15) . . ?
C3 C2 N1 110.62(15) . . ?
C3 C2 C10 141.41(17) . . ?
C21 C16 C15 106.58(17) . . ?
C17 C16 C21 118.72(18) . . ?
C17 C16 C15 134.62(18) . . ?
N1 C9 C4 106.38(16) . . ?
N1 C9 C8 131.08(18) . . ?
C8 C9 C4 122.41(18) . . ?
N13 C21 C16 107.69(17) . . ?
N13 C21 C20 129.7(2) . . ?
C20 C21 C16 122.5(2) . . ?
C10 C11 H11 124.7 . . ?
C12 C11 H11 124.7 . . ?
C12 C11 C10 110.67(17) . . ?
C4 C5 H5 121.1 . . ?
C6 C5 H5 121.1 . . ?
C6 C5 C4 117.76(18) . . ?
C9 C4 C3 108.50(17) . . ?
C5 C4 C9 119.43(17) . . ?
C5 C4 C3 131.91(18) . . ?
C2 C3 C4 105.11(16) . . ?
C2 C3 C28 128.42(17) . . ?
C4 C3 C28 126.47(17) . . ?
F23 C22 F24 106.63(17) . . ?
F23 C22 F25 106.88(17) . . ?
F23 C22 C10 111.86(16) . . ?
F24 C22 C10 112.32(16) . . ?
F25 C22 F24 107.10(17) . . ?
F25 C22 C10 111.70(17) . . ?
C16 C17 H17 120.7 . . ?
C18 C17 C16 118.69(19) . . ?
C18 C17 H17 120.7 . . ?
C16 C15 C10 124.20(16) . . ?
C14 C15 C16 106.48(17) . . ?
C14 C15 C10 129.10(17) . . ?
C9 C8 H8 121.4 . . ?
C7 C8 C9 117.23(18) . . ?
C7 C8 H8 121.4 . . ?
C8 C7 H7 119.4 . . ?
C8 C7 C6 121.20(18) . . ?
C6 C7 H7 119.4 . . ?
O26 C6 C7 114.06(17) . . ?
C5 C6 O26 124.00(18) . . ?
C5 C6 C7 121.94(18) . . ?
N13 C14 C15 110.04(18) . . ?
N13 C14 H14 125.0 . . ?
C15 C14 H14 125.0 . . ?
C2 C10 C11 100.36(15) . . ?
C2 C10 C22 109.04(15) . . ?
C22 C10 C11 108.35(16) . . ?
C15 C10 C2 113.47(15) . . ?
C15 C10 C11 112.68(16) . . ?
C15 C10 C22 112.21(16) . . ?
O26 C27 H27A 109.5 . . ?
O26 C27 H27B 109.5 . . ?
O26 C27 H27C 109.5 . . ?
H27A C27 H27B 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
N1 C12 H12 125.1 . . ?
C11 C12 N1 109.84(18) . . ?
C11 C12 H12 125.1 . . ?
C3 C28 H28A 109.5 . . ?
C3 C28 H28B 109.5 . . ?
C3 C28 H28C 109.5 . . ?
H28A C28 H28B 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C21 C20 H20 121.4 . . ?
C19 C20 C21 117.1(2) . . ?
C19 C20 H20 121.4 . . ?
C17 C18 H18 119.3 . . ?
C17 C18 C19 121.4(2) . . ?
C19 C18 H18 119.3 . . ?
C20 C19 C18 121.6(2) . . ?
C20 C19 H19 119.2 . . ?
C18 C19 H19 119.2 . . ?

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
F23 C22 C10 C2 52.1(2) . . . . ?
F23 C22 C10 C11 -56.3(2) . . . . ?
F23 C22 C10 C15 178.68(16) . . . . ?
F24 C22 C10 C2 -67.8(2) . . . . ?
F24 C22 C10 C11 -176.14(16) . . . . ?
F24 C22 C10 C15 58.8(2) . . . . ?
F25 C22 C10 C2 171.84(17) . . . . ?
F25 C22 C10 C11 63.5(2) . . . . ?
F25 C22 C10 C15 -61.6(2) . . . . ?
N1 C2 C3 C4 0.9(2) . . . . ?
N1 C2 C3 C28 -179.48(19) . . . . ?
N1 C2 C10 C11 4.07(19) . . . . ?
N1 C2 C10 C22 -109.61(17) . . . . ?
N1 C2 C10 C15 124.52(17) . . . . ?
N1 C9 C4 C5 -176.40(16) . . . . ?
N1 C9 C4 C3 -0.5(2) . . . . ?
N1 C9 C8 C7 174.2(2) . . . . ?
N13 C21 C20 C19 176.6(2) . . . . ?
C2 N1 C9 C4 1.0(2) . . . . ?
C2 N1 C9 C8 -174.8(2) . . . . ?
C2 N1 C12 C11 3.0(2) . . . . ?
C16 C21 C20 C19 -0.4(3) . . . . ?
C16 C17 C18 C19 -0.5(3) . . . . ?
C16 C15 C14 N13 0.5(2) . . . . ?
C16 C15 C10 C2 -41.8(3) . . . . ?
C16 C15 C10 C11 71.4(2) . . . . ?
C16 C15 C10 C22 -166.00(17) . . . . ?
C9 N1 C2 C3 -1.3(2) . . . . ?
C9 N1 C2 C10 -179.33(15) . . . . ?
C9 N1 C12 C11 175.4(2) . . . . ?
C9 C4 C3 C2 -0.3(2) . . . . ?
C9 C4 C3 C28 -179.89(19) . . . . ?
C9 C8 C7 C6 0.8(3) . . . . ?
C21 N13 C14 C15 -0.8(2) . . . . ?
C21 C16 C17 C18 0.4(3) . . . . ?
C21 C16 C15 C14 -0.1(2) . . . . ?
C21 C16 C15 C10 -175.16(18) . . . . ?
C21 C20 C19 C18 0.3(3) . . . . ?
C5 C4 C3 C2 174.97(19) . . . . ?
C5 C4 C3 C28 -4.6(3) . . . . ?
C4 C9 C8 C7 -1.0(3) . . . . ?
C4 C5 C6 O26 177.47(17) . . . . ?
C4 C5 C6 C7 -1.8(3) . . . . ?
C3 C2 C10 C11 -173.0(2) . . . . ?
C3 C2 C10 C22 73.3(3) . . . . ?
C3 C2 C10 C15 -52.6(3) . . . . ?
C17 C16 C21 N13 -177.52(18) . . . . ?
C17 C16 C21 C20 0.0(3) . . . . ?
C17 C16 C15 C14 176.4(2) . . . . ?
C17 C16 C15 C10 1.3(4) . . . . ?
C17 C18 C19 C20 0.1(3) . . . . ?
C15 C16 C21 N13 -0.4(2) . . . . ?
C15 C16 C21 C20 177.15(19) . . . . ?
C15 C16 C17 C18 -175.7(2) . . . . ?
C8 C9 C4 C5 -0.1(3) . . . . ?
C8 C9 C4 C3 175.83(17) . . . . ?
C8 C7 C6 O26 -178.68(18) . . . . ?
C8 C7 C6 C5 0.7(3) . . . . ?
C6 C5 C4 C9 1.5(3) . . . . ?
C6 C5 C4 C3 -173.29(18) . . . . ?
C14 N13 C21 C16 0.7(2) . . . . ?
C14 N13 C21 C20 -176.6(2) . . . . ?
C14 C15 C10 C2 144.2(2) . . . . ?
C14 C15 C10 C11 -102.6(2) . . . . ?
C14 C15 C10 C22 20.0(3) . . . . ?
C10 C2 C3 C4 178.0(2) . . . . ?
C10 C2 C3 C28 -2.4(4) . . . . ?
C10 C11 C12 N1 -0.1(2) . . . . ?
C10 C15 C14 N13 175.29(19) . . . . ?
C27 O26 C6 C5 7.9(3) . . . . ?
C27 O26 C6 C7 -172.78(18) . . . . ?
C12 N1 C2 C3 173.53(17) . . . . ?
C12 N1 C2 C10 -4.5(2) . . . . ?
C12 N1 C9 C4 -171.5(2) . . . . ?
C12 N1 C9 C8 12.7(4) . . . . ?
C12 C11 C10 C2 -2.4(2) . . . . ?
C12 C11 C10 C22 111.77(19) . . . . ?
C12 C11 C10 C15 -123.45(19) . . . . ?

_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 1.828
_oxdiff_exptl_absorpt_empirical_full_min 0.540
####################################################################### 
# 
# 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_zhuwr_201007
_database_code_depnum_ccdc_archive 'CCDC 2101639'
loop_
_audit_author_name
_audit_author_address
'Frank Allen'
;The Cambridge Crystallographic Data Centre
China
;
_audit_update_record             
;
2021-08-05 deposited with the CCDC.	2021-11-19 downloaded from the CCDC.
;
_audit_creation_date             2020-10-07
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C27 H18 Br F3 N2'
_chemical_formula_sum            'C27 H18 Br F3 N2'
_chemical_formula_weight         507.34
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         CHNOBr
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'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   10.1505(2)
_cell_length_b                   19.0261(9)
_cell_length_c                   11.5778(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2235.96(14)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7727
_cell_measurement_temperature    300.28(15)
_cell_measurement_theta_max      74.4370
_cell_measurement_theta_min      3.8130
_shelx_estimated_absorpt_T_max   0.870
_shelx_estimated_absorpt_T_min   0.813
_exptl_absorpt_coefficient_mu    2.876
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.86865
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.54a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.507
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1024
_exptl_crystal_size_max          0.075
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0950
_diffrn_reflns_av_unetI/netI     0.0497
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            22787
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.813
_diffrn_reflns_theta_min         4.470
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      300.28(15)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -127.00 -27.00   0.50    3.00    -- -100.00  85.00-140.00  200
  2  ω   -173.00 -82.00   0.50    3.00    -- -100.00-103.00  10.00  182
  3  ω   -174.00 -85.00   0.50    3.00    -- -100.00 -43.00-131.00  178
  4  ω   -119.00 -71.00   0.50    0.30    --  -46.62-125.00   0.00   96
  5  ω   -119.00 -71.00   0.50    0.30    --  -46.62-125.00  60.00   96
  6  ω    -27.00  61.00   0.50    0.30    --   46.62 -38.00 120.00  176
  7  ω     32.00 123.00   0.50    3.00    --  107.00 -30.00 120.00  182
  8  ω     83.00 178.00   0.50    3.00    --  107.00  77.00 150.00  190
  9  ω     93.00 178.00   0.50    3.00    --  107.00  45.00 -30.00  170
 10  ω     93.00 178.00   0.50    3.00    --  107.00  45.00 -60.00  170
 11  ω     34.00 109.00   0.50    3.00    --  107.00 -94.00-180.00  150
 12  ω     34.00 109.00   0.50    3.00    --  107.00 -94.00-150.00  150
 13  ω     34.00 109.00   0.50    3.00    --  107.00 -94.00-120.00  150
 14  ω     34.00 109.00   0.50    3.00    --  107.00 -94.00 -60.00  150
 15  ω     34.00 109.00   0.50    3.00    --  107.00 -94.00 150.00  150
 16  ω     23.00  75.00   0.50    0.30    --   46.62  77.00 120.00  104
 17  ω     23.00 120.00   0.50    0.30    --   46.62  77.00-120.00  194
 18  ω    -26.00  61.00   0.50    0.30    --   46.62 -43.00-131.00  174
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0470217000
_diffrn_orient_matrix_UB_12      -0.0671917000
_diffrn_orient_matrix_UB_13      0.0616923000
_diffrn_orient_matrix_UB_21      -0.0676919000
_diffrn_orient_matrix_UB_22      0.0247268000
_diffrn_orient_matrix_UB_23      0.1118239000
_diffrn_orient_matrix_UB_31      -0.1274328000
_diffrn_orient_matrix_UB_32      -0.0378954000
_diffrn_orient_matrix_UB_33      -0.0371645000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.742
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.968
_reflns_number_gt                3875
_reflns_number_total             4631
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     71.98
_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 1.171.40.54a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.54a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.54a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.569
_refine_diff_density_min         -0.653
_refine_diff_density_rms         0.078
_refine_ls_abs_structure_details 
;
 Flack x determined using 1282 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.03(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.111
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     299
_refine_ls_number_reflns         4631
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0832
_refine_ls_R_factor_gt           0.0748
_refine_ls_restrained_S_all      1.111
_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)+(0.0923P)²+2.9016P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2167
_refine_ls_wR_factor_ref         0.2233
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N008(H008), C00D(H00D), C00K(H00K), C00L(H00L), C00M(H00M), C00N(H00N),
 C00O(H00O), C00Q(H00Q), C00R(H00R), C00S(H00S), C00T(H00T), C00U(H00U),
 C00V(H00V), C00W(H00W), C00X(H00X)
2.b Idealised Me refined as rotating group:
 C00F(H00A,H00B,H00C)
;
_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
Br01 Br 0.85121(10) 0.65392(7) 0.49411(11) 0.0949(5) Uani 1 1 d . . . . .
F002 F 0.6704(8) 0.4858(4) 0.4148(7) 0.105(2) Uani 1 1 d . . . . .
F003 F 0.8389(7) 0.5265(4) 0.3241(8) 0.106(2) Uani 1 1 d . . . . .
F004 F 0.6691(8) 0.4941(3) 0.2278(7) 0.103(2) Uani 1 1 d . . . . .
N005 N 0.5048(7) 0.5934(4) 0.3470(8) 0.0683(19) Uani 1 1 d . . . . .
C006 C 0.4012(8) 0.5793(5) 0.2709(9) 0.063(2) Uani 1 1 d . . . . .
C007 C 0.3221(9) 0.6161(5) 0.4514(10) 0.070(2) Uani 1 1 d . . . . .
N008 N 0.8049(9) 0.6981(6) 0.0985(10) 0.099(3) Uani 1 1 d . . . . .
H008 H 0.864654 0.704257 0.046801 0.119 Uiso 1 1 calc R U . . .
C009 C 0.6496(8) 0.6006(5) 0.3320(8) 0.065(2) Uani 1 1 d . . . . .
C00A C 0.6313(10) 0.7146(5) 0.2137(9) 0.069(2) Uani 1 1 d . . . . .
C00B C 0.2845(8) 0.5927(5) 0.3360(9) 0.066(2) Uani 1 1 d . . . . .
C00C C 0.5698(8) 0.6372(5) 0.5204(9) 0.067(2) Uani 1 1 d . . . . .
C00D C 0.2750(11) 0.5479(6) 0.1084(11) 0.081(3) Uani 1 1 d . . . . .
H00D H 0.268444 0.531473 0.033007 0.097 Uiso 1 1 calc R U . . .
C00E C 0.6882(8) 0.6488(6) 0.2396(8) 0.068(2) Uani 1 1 d . . . . .
C00F C 0.2300(10) 0.6401(7) 0.5442(11) 0.086(3) Uani 1 1 d . . . . .
H00A H 0.169950 0.674154 0.513076 0.129 Uiso 1 1 calc R U . . .
H00B H 0.279559 0.660907 0.605951 0.129 Uiso 1 1 calc R U . . .
H00C H 0.181296 0.600556 0.573138 0.129 Uiso 1 1 calc R U . . .
C00G C 0.4583(9) 0.6156(5) 0.4511(9) 0.066(2) Uani 1 1 d . . . . .
C00H C 0.7061(10) 0.7461(6) 0.1247(10) 0.079(3) Uani 1 1 d . . . . .
C00I C 0.6781(8) 0.6305(5) 0.4550(10) 0.070(2) Uani 1 1 d . . . . .
C00J C 0.5633(9) 0.6559(5) 0.6441(9) 0.069(2) Uani 1 1 d . . . . .
C00K C 0.4973(12) 0.6107(6) 0.7211(10) 0.078(3) Uani 1 1 d . . . . .
H00K H 0.454690 0.571314 0.691541 0.094 Uiso 1 1 calc R U . . .
C00L C 0.1634(10) 0.5817(6) 0.2835(11) 0.080(3) Uani 1 1 d . . . . .
H00L H 0.085504 0.587994 0.324469 0.096 Uiso 1 1 calc R U . . .
C00M C 0.6798(13) 0.8115(7) 0.0817(12) 0.092(3) Uani 1 1 d . . . . .
H00M H 0.734750 0.831482 0.026454 0.111 Uiso 1 1 calc R U . . .
C00N C 0.3982(10) 0.5585(5) 0.1559(10) 0.074(2) Uani 1 1 d . . . . .
H00N H 0.474873 0.552107 0.113212 0.089 Uiso 1 1 calc R U . . .
C00O C 0.4935(13) 0.6223(7) 0.8363(12) 0.090(3) Uani 1 1 d . . . . .
H00O H 0.449955 0.590738 0.884403 0.108 Uiso 1 1 calc R U . . .
C00P C 0.7063(11) 0.5264(7) 0.3227(13) 0.091(3) Uani 1 1 d . . . . .
C00Q C 0.1610(11) 0.5612(5) 0.1704(11) 0.083(3) Uani 1 1 d . . . . .
H00Q H 0.079984 0.556100 0.133782 0.100 Uiso 1 1 calc R U . . .
C00R C 0.6244(12) 0.7151(6) 0.6894(10) 0.083(3) Uani 1 1 d . . . . .
H00R H 0.669114 0.746091 0.641206 0.099 Uiso 1 1 calc R U . . .
C00S C 0.5537(13) 0.6805(8) 0.8825(12) 0.097(4) Uani 1 1 d . . . . .
H00S H 0.552389 0.689008 0.961615 0.116 Uiso 1 1 calc R U . . .
C00T C 0.5213(11) 0.7515(6) 0.2530(11) 0.079(3) Uani 1 1 d . . . . .
H00T H 0.467185 0.732503 0.309839 0.095 Uiso 1 1 calc R U . . .
C00U C 0.6182(15) 0.7272(8) 0.8052(13) 0.105(4) Uani 1 1 d . . . . .
H00U H 0.657573 0.767563 0.834746 0.126 Uiso 1 1 calc R U . . .
C00V C 0.7936(11) 0.6409(7) 0.1653(12) 0.094(3) Uani 1 1 d . . . . .
H00V H 0.848475 0.601837 0.162115 0.113 Uiso 1 1 calc R U . . .
C00W C 0.5733(15) 0.8468(7) 0.1202(12) 0.098(3) Uani 1 1 d . . . . .
H00W H 0.552899 0.890661 0.089747 0.118 Uiso 1 1 calc R U . . .
C00X C 0.4939(14) 0.8175(7) 0.2056(12) 0.093(3) Uani 1 1 d . . . . .
H00X H 0.420871 0.842345 0.231712 0.112 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
Br01 C00I 1.869(9) . ?
F002 C00P 1.366(16) . ?
F003 C00P 1.346(13) . ?
F004 C00P 1.314(15) . ?
N005 C006 1.398(12) . ?
N005 C009 1.486(10) . ?
N005 C00G 1.362(13) . ?
C006 C00B 1.427(13) . ?
C006 C00N 1.389(15) . ?
C007 C00B 1.458(15) . ?
C007 C00F 1.496(15) . ?
C007 C00G 1.383(13) . ?
N008 H008 0.8600 . ?
N008 C00H 1.390(15) . ?
N008 C00V 1.340(17) . ?
C009 C00E 1.464(14) . ?
C009 C00I 1.560(14) . ?
C009 C00P 1.528(15) . ?
C00A C00E 1.411(14) . ?
C00A C00H 1.414(15) . ?
C00A C00T 1.394(14) . ?
C00B C00L 1.388(14) . ?
C00C C00G 1.447(13) . ?
C00C C00I 1.341(13) . ?
C00C C00J 1.477(15) . ?
C00D H00D 0.9300 . ?
C00D C00N 1.380(15) . ?
C00D C00Q 1.386(17) . ?
C00E C00V 1.381(14) . ?
C00F H00A 0.9600 . ?
C00F H00B 0.9600 . ?
C00F H00C 0.9600 . ?
C00H C00M 1.366(17) . ?
C00J C00K 1.408(15) . ?
C00J C00R 1.390(15) . ?
C00K H00K 0.9300 . ?
C00K C00O 1.353(18) . ?
C00L H00L 0.9300 . ?
C00L C00Q 1.366(17) . ?
C00M H00M 0.9300 . ?
C00M C00W 1.35(2) . ?
C00N H00N 0.9300 . ?
C00O H00O 0.9300 . ?
C00O C00S 1.374(19) . ?
C00Q H00Q 0.9300 . ?
C00R H00R 0.9300 . ?
C00R C00U 1.362(18) . ?
C00S H00S 0.9300 . ?
C00S C00U 1.42(2) . ?
C00T H00T 0.9300 . ?
C00T C00X 1.398(18) . ?
C00U H00U 0.9300 . ?
C00V H00V 0.9300 . ?
C00W H00W 0.9300 . ?
C00W C00X 1.39(2) . ?
C00X H00X 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
C006 N005 C009 133.5(8) . . ?
C00G N005 C006 110.9(7) . . ?
C00G N005 C009 114.6(8) . . ?
N005 C006 C00B 104.9(8) . . ?
C00N C006 N005 132.5(9) . . ?
C00N C006 C00B 122.6(9) . . ?
C00B C007 C00F 126.0(9) . . ?
C00G C007 C00B 104.9(9) . . ?
C00G C007 C00F 128.9(11) . . ?
C00H N008 H008 124.9 . . ?
C00V N008 H008 124.9 . . ?
C00V N008 C00H 110.2(9) . . ?
N005 C009 C00I 96.4(7) . . ?
N005 C009 C00P 107.2(8) . . ?
C00E C009 N005 114.0(8) . . ?
C00E C009 C00I 112.9(7) . . ?
C00E C009 C00P 115.3(9) . . ?
C00P C009 C00I 109.4(9) . . ?
C00E C00A C00H 108.1(9) . . ?
C00T C00A C00E 134.8(10) . . ?
C00T C00A C00H 117.1(10) . . ?
C006 C00B C007 108.7(8) . . ?
C00L C00B C006 118.5(10) . . ?
C00L C00B C007 132.8(10) . . ?
C00G C00C C00J 124.8(8) . . ?
C00I C00C C00G 107.5(9) . . ?
C00I C00C C00J 127.4(9) . . ?
C00N C00D H00D 119.2 . . ?
C00N C00D C00Q 121.6(11) . . ?
C00Q C00D H00D 119.2 . . ?
C00A C00E C009 127.0(8) . . ?
C00V C00E C009 126.5(10) . . ?
C00V C00E C00A 106.4(10) . . ?
C007 C00F H00A 109.5 . . ?
C007 C00F H00B 109.5 . . ?
C007 C00F H00C 109.5 . . ?
H00A C00F H00B 109.5 . . ?
H00A C00F H00C 109.5 . . ?
H00B C00F H00C 109.5 . . ?
N005 C00G C007 110.5(9) . . ?
N005 C00G C00C 107.9(8) . . ?
C007 C00G C00C 141.2(10) . . ?
N008 C00H C00A 105.6(10) . . ?
C00M C00H N008 131.3(11) . . ?
C00M C00H C00A 123.1(11) . . ?
C009 C00I Br01 118.9(7) . . ?
C00C C00I Br01 127.7(8) . . ?
C00C C00I C009 113.5(8) . . ?
C00K C00J C00C 119.3(9) . . ?
C00R C00J C00C 122.7(10) . . ?
C00R C00J C00K 118.0(10) . . ?
C00J C00K H00K 118.7 . . ?
C00O C00K C00J 122.6(11) . . ?
C00O C00K H00K 118.7 . . ?
C00B C00L H00L 120.7 . . ?
C00Q C00L C00B 118.6(11) . . ?
C00Q C00L H00L 120.7 . . ?
C00H C00M H00M 120.4 . . ?
C00W C00M C00H 119.3(12) . . ?
C00W C00M H00M 120.4 . . ?
C006 C00N H00N 121.8 . . ?
C00D C00N C006 116.3(10) . . ?
C00D C00N H00N 121.8 . . ?
C00K C00O H00O 119.9 . . ?
C00K C00O C00S 120.2(12) . . ?
C00S C00O H00O 119.9 . . ?
F002 C00P C009 111.5(10) . . ?
F003 C00P F002 105.0(11) . . ?
F003 C00P C009 112.0(9) . . ?
F004 C00P F002 108.2(10) . . ?
F004 C00P F003 107.3(11) . . ?
F004 C00P C009 112.5(10) . . ?
C00D C00Q H00Q 118.9 . . ?
C00L C00Q C00D 122.2(10) . . ?
C00L C00Q H00Q 118.9 . . ?
C00J C00R H00R 120.4 . . ?
C00U C00R C00J 119.3(11) . . ?
C00U C00R H00R 120.4 . . ?
C00O C00S H00S 121.2 . . ?
C00O C00S C00U 117.7(12) . . ?
C00U C00S H00S 121.2 . . ?
C00A C00T H00T 120.6 . . ?
C00A C00T C00X 118.9(11) . . ?
C00X C00T H00T 120.6 . . ?
C00R C00U C00S 122.3(12) . . ?
C00R C00U H00U 118.8 . . ?
C00S C00U H00U 118.8 . . ?
N008 C00V C00E 109.7(11) . . ?
N008 C00V H00V 125.1 . . ?
C00E C00V H00V 125.1 . . ?
C00M C00W H00W 120.0 . . ?
C00M C00W C00X 120.0(13) . . ?
C00X C00W H00W 120.0 . . ?
C00T C00X H00X 119.2 . . ?
C00W C00X C00T 121.5(12) . . ?
C00W C00X H00X 119.2 . . ?

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
N005 C006 C00B C007 0.8(10) . . . . ?
N005 C006 C00B C00L -178.6(9) . . . . ?
N005 C006 C00N C00D 178.7(10) . . . . ?
N005 C009 C00E C00A 41.8(13) . . . . ?
N005 C009 C00E C00V -143.0(11) . . . . ?
N005 C009 C00I Br01 -178.8(6) . . . . ?
N005 C009 C00I C00C 0.2(10) . . . . ?
N005 C009 C00P F002 -54.6(11) . . . . ?
N005 C009 C00P F003 -171.9(11) . . . . ?
N005 C009 C00P F004 67.1(12) . . . . ?
C006 N005 C009 C00E 50.8(14) . . . . ?
C006 N005 C009 C00I 169.3(10) . . . . ?
C006 N005 C009 C00P -78.1(13) . . . . ?
C006 N005 C00G C007 1.4(12) . . . . ?
C006 N005 C00G C00C -173.3(8) . . . . ?
C006 C00B C00L C00Q -2.8(14) . . . . ?
C007 C00B C00L C00Q 178.0(10) . . . . ?
N008 C00H C00M C00W 177.9(13) . . . . ?
C009 N005 C006 C00B -169.3(10) . . . . ?
C009 N005 C006 C00N 9.0(18) . . . . ?
C009 N005 C00G C007 171.8(8) . . . . ?
C009 N005 C00G C00C -2.8(11) . . . . ?
C009 C00E C00V N008 -174.9(10) . . . . ?
C00A C00E C00V N008 1.1(14) . . . . ?
C00A C00H C00M C00W -4.0(19) . . . . ?
C00A C00T C00X C00W 0(2) . . . . ?
C00B C006 C00N C00D -3.2(14) . . . . ?
C00B C007 C00G N005 -0.8(11) . . . . ?
C00B C007 C00G C00C 171.0(13) . . . . ?
C00B C00L C00Q C00D 3.3(16) . . . . ?
C00C C00J C00K C00O 176.3(11) . . . . ?
C00C C00J C00R C00U -177.4(12) . . . . ?
C00E C009 C00I Br01 -59.3(9) . . . . ?
C00E C009 C00I C00C 119.6(9) . . . . ?
C00E C009 C00P F002 177.3(8) . . . . ?
C00E C009 C00P F003 59.9(14) . . . . ?
C00E C009 C00P F004 -61.0(12) . . . . ?
C00E C00A C00H N008 0.6(12) . . . . ?
C00E C00A C00H C00M -177.9(11) . . . . ?
C00E C00A C00T C00X -179.5(12) . . . . ?
C00F C007 C00B C006 175.8(9) . . . . ?
C00F C007 C00B C00L -5.0(18) . . . . ?
C00F C007 C00G N005 -176.4(10) . . . . ?
C00F C007 C00G C00C -5(2) . . . . ?
C00G N005 C006 C00B -1.3(10) . . . . ?
C00G N005 C006 C00N 177.0(10) . . . . ?
C00G N005 C009 C00E -116.9(10) . . . . ?
C00G N005 C009 C00I 1.7(10) . . . . ?
C00G N005 C009 C00P 114.2(10) . . . . ?
C00G C007 C00B C006 0.0(11) . . . . ?
C00G C007 C00B C00L 179.2(11) . . . . ?
C00G C00C C00I Br01 177.1(7) . . . . ?
C00G C00C C00I C009 -1.8(11) . . . . ?
C00G C00C C00J C00K 48.6(14) . . . . ?
C00G C00C C00J C00R -134.1(11) . . . . ?
C00H N008 C00V C00E -0.8(16) . . . . ?
C00H C00A C00E C009 174.9(9) . . . . ?
C00H C00A C00E C00V -1.1(12) . . . . ?
C00H C00A C00T C00X -2.0(16) . . . . ?
C00H C00M C00W C00X 2(2) . . . . ?
C00I C009 C00E C00A -66.9(12) . . . . ?
C00I C009 C00E C00V 108.3(12) . . . . ?
C00I C009 C00P F002 48.9(11) . . . . ?
C00I C009 C00P F003 -68.5(13) . . . . ?
C00I C009 C00P F004 170.5(9) . . . . ?
C00I C00C C00G N005 2.7(11) . . . . ?
C00I C00C C00G C007 -169.2(13) . . . . ?
C00I C00C C00J C00K -124.5(11) . . . . ?
C00I C00C C00J C00R 52.8(15) . . . . ?
C00J C00C C00G N005 -171.5(9) . . . . ?
C00J C00C C00G C007 17(2) . . . . ?
C00J C00C C00I Br01 -8.8(15) . . . . ?
C00J C00C C00I C009 172.3(9) . . . . ?
C00J C00K C00O C00S 1.0(19) . . . . ?
C00J C00R C00U C00S 2(2) . . . . ?
C00K C00J C00R C00U -0.1(17) . . . . ?
C00K C00O C00S C00U 0(2) . . . . ?
C00M C00W C00X C00T 0(2) . . . . ?
C00N C006 C00B C007 -177.7(8) . . . . ?
C00N C006 C00B C00L 2.9(14) . . . . ?
C00N C00D C00Q C00L -3.8(17) . . . . ?
C00O C00S C00U C00R -2(2) . . . . ?
C00P C009 C00E C00A 166.5(9) . . . . ?
C00P C009 C00E C00V -18.3(15) . . . . ?
C00P C009 C00I Br01 70.4(9) . . . . ?
C00P C009 C00I C00C -110.6(9) . . . . ?
C00Q C00D C00N C006 3.6(16) . . . . ?
C00R C00J C00K C00O -1.1(17) . . . . ?
C00T C00A C00E C009 -7.4(19) . . . . ?
C00T C00A C00E C00V 176.6(13) . . . . ?
C00T C00A C00H N008 -177.5(10) . . . . ?
C00T C00A C00H C00M 4.0(17) . . . . ?
C00V N008 C00H C00A 0.1(14) . . . . ?
C00V N008 C00H C00M 178.4(13) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.278
_oxdiff_exptl_absorpt_empirical_full_min 0.793
####################################################################### 
# 
# 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_20210325-zwr-1
_database_code_depnum_ccdc_archive 'CCDC 2101638'
loop_
_audit_author_name
_audit_author_address
'Frank Allen'
;The Cambridge Crystallographic Data Centre
China
;
_audit_update_record             
;
2021-08-05 deposited with the CCDC.	2021-11-19 downloaded from the CCDC.
;
_audit_creation_date             2021-03-26
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C25 H22 F4 N2 O'
_chemical_formula_sum            'C25 H22 F4 N2 O'
_chemical_formula_weight         442.44
_chemical_absolute_configuration ad
_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'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   10.3110(2)
_cell_length_b                   12.3464(2)
_cell_length_c                   34.9989(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4455.49(14)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    16755
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      75.9130
_cell_measurement_theta_min      2.4940
_shelx_estimated_absorpt_T_max   0.957
_shelx_estimated_absorpt_T_min   0.879
_exptl_absorpt_coefficient_mu    0.881
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.73121
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
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    1.319
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1840
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1344
_diffrn_reflns_av_unetI/netI     0.0712
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_limit_l_min       -44
_diffrn_reflns_number            55083
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.968
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.255
_diffrn_reflns_theta_min         2.525
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.981
_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  26.00   0.50    4.00    --  -46.62  19.00 -60.00   98
  2  ω    -67.00 -41.00   0.50   15.00    -- -100.00  61.00-180.00   52
  3  ω    -67.00 -30.00   0.50   15.00    -- -100.00  61.00-150.00   74
  4  ω    -94.00 -29.00   0.50   15.00    -- -100.00  91.00  18.00  130
  5  ω     34.00 102.00   0.50    4.00    --   46.62  44.00 169.00  136
  6  ω   -104.00 -78.00   0.50    4.00    --  -46.62-125.00 -60.00   52
  7  ω   -112.00 -74.00   0.50    4.00    --  -46.62-125.00 150.00   76
  8  ω     59.00  88.00   0.50   15.00    --  105.44 -94.00 166.00   58
  9  ω     95.00 178.00   0.50   15.00    --  105.44  44.00 169.00  166
 10  ω     39.00  69.00   0.50   15.00    --  105.44 -61.00-120.00   60
 11  ω     71.00 102.00   0.50   15.00    --  105.44 -94.00-150.00   62
 12  ω     38.00  64.00   0.50   15.00    --  105.44 -61.00 -30.00   52
 13  ω     37.00  73.00   0.50   15.00    --  105.44 -61.00 -60.00   72
 14  ω     91.00 136.00   0.50   20.00    --  105.44  94.00 -82.00   90
 15  ω    -39.00 -13.00   0.50    6.00    --  -46.37  38.00-120.00   52
 16  ω     -2.00  24.00   0.50    6.00    --  -46.37  38.00-120.00   52
 17  ω     -9.00  28.00   0.50    6.00    --   46.37 -19.00  30.00   74
 18  ω   -132.00 -94.00   0.50   20.00    -- -100.00 -45.00-150.00   76
 19  ω    -55.00 -29.00   0.50   20.00    -- -100.00 125.00-150.00   52
 20  ω    -97.00 -68.00   0.50   20.00    -- -100.00 125.00-150.00   58
 21  ω     33.00  59.00   0.50   20.00    --  105.44 -61.00 -90.00   52
 22  ω     78.00 110.00   0.50   20.00    --  105.44-125.00 120.00   64
 23  ω     39.00  68.00   0.50   20.00    --  105.44 -61.00-150.00   58
 24  ω     34.00  61.00   0.50   20.00    --  105.44-125.00 120.00   54
 25  ω     92.00 130.00   0.50   20.00    --  105.44  45.00-180.00   76
 26  ω    138.00 165.00   0.50   20.00    --  105.44  45.00-180.00   54
 27  ω     42.00  68.00   0.50   20.00    --  105.44 -61.00-180.00   52
 28  ω     44.00  70.00   0.50   20.00    --  105.44 -61.00   0.00   52
 29  ω    138.00 164.00   0.50   20.00    --  105.44  94.00 -82.00   52
 30  ω     30.00 118.00   0.50    6.00    --   46.37  57.00  60.00  176
 31  ω     30.00 118.00   0.50    6.00    --   46.37  57.00-120.00  176
 32  ω     18.00  95.00   0.50    6.00    --   46.37-125.00 120.00  154
 33  ω     23.00 118.00   0.50    6.00    --   46.37  77.00 150.00  190
 34  ω     23.00  48.00   0.50    6.00    --   46.37  77.00   0.00   50
 35  ω     30.00 118.00   0.50    6.00    --   46.37  57.00 -30.00  176
 36  ω    -49.00 -24.00   0.50    6.00    --  -46.37  91.00  18.00   50
 37  ω    -49.00 -24.00   0.50    6.00    --  -46.37  91.00  18.00   50
 38  ω      2.00  27.00   0.50    6.00    --   46.37 -91.00 -94.00   50
 39  ω    -49.00 -24.00   0.50    6.00    --  -46.37  91.00  18.00   50
 40  ω    -49.00 -24.00   0.50    6.00    --  -46.37  91.00  18.00   50
 41  ω     35.00  61.00   0.50   20.00    --  107.00 -94.00 166.00   52
 42  ω     43.00  69.00   0.50   20.00    --  107.00-125.00 150.00   52
 43  ω     84.00 110.00   0.50   20.00    --  107.00-125.00 150.00   52
 44  ω     83.00 108.00   0.50   20.00    --  107.00  77.00-150.00   50
 45  ω    137.00 175.00   0.50   20.00    --  107.00  77.00-150.00   76
 46  ω     45.00  76.00   0.50   20.00    --  107.00 -77.00-120.00   62
 47  ω     85.00 111.00   0.50   20.00    --  107.00  77.00-180.00   52
 48  ω    125.00 174.00   0.50   20.00    --  107.00  77.00-180.00   98
 49  ω     37.00  63.00   0.50   20.00    --  107.00 -77.00-180.00   52
 50  ω     34.00  64.00   0.50   20.00    --  107.00 -94.00   0.00   60
 51  ω     42.00  68.00   0.50   20.00    --  107.00 -77.00 -90.00   52
 52  ω     78.00 104.00   0.50   20.00    --  107.00 -94.00 166.00   52
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1076116000
_diffrn_orient_matrix_UB_12      0.0049250000
_diffrn_orient_matrix_UB_13      -0.0304619000
_diffrn_orient_matrix_UB_21      -0.0844292000
_diffrn_orient_matrix_UB_22      -0.0681313000
_diffrn_orient_matrix_UB_23      -0.0272719000
_diffrn_orient_matrix_UB_31      -0.0600572000
_diffrn_orient_matrix_UB_32      0.1043956000
_diffrn_orient_matrix_UB_33      -0.0163454000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.764
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.951
_reflns_number_gt                7302
_reflns_number_total             9142
_reflns_odcompleteness_completeness 99.98
_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 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.290
_refine_diff_density_min         -0.278
_refine_diff_density_rms         0.059
_refine_ls_abs_structure_details 
;
 Flack x determined using 2600 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.11(8)
_refine_ls_extinction_coef       0.00057(12)
_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   1.051
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     590
_refine_ls_number_reflns         9142
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0718
_refine_ls_R_factor_gt           0.0517
_refine_ls_restrained_S_all      1.051
_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)+(0.0612P)²+1.2463P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1200
_refine_ls_wR_factor_ref         0.1343
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N41(H41), N63(H63), N23(H23), C27(H27), C36(H36), C8(H8), C2(H2), C5(H5),
 C58(H58), C7(H7), C38(H38), C33(H33), C60(H60), C24(H24), C39(H39), C55(H55),
 C30(H30), C61(H61), C29(H29)
2.b Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C), C47(H47A,H47B,H47C), C54(H54A,H54B,H54C), C15(H15A,H15B,
 H15C), C48(H48A,H48B,H48C), C16(H16A,H16B,H16C), C14(H14A,H14B,H14C), C46(H46A,
 H46B,H46C)
;
_atom_sites_solution_hydrogens   mixed
_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
F18 F 0.9359(2) 0.74999(18) 0.55689(7) 0.0348(5) Uani 1 1 d . . . . .
F50 F 0.8156(2) 0.44765(19) 0.59593(7) 0.0341(5) Uani 1 1 d . . . . .
F20 F 1.0942(2) 0.84369(18) 0.57942(7) 0.0332(5) Uani 1 1 d . . . . .
F19 F 0.9676(2) 0.91282(19) 0.53700(7) 0.0361(6) Uani 1 1 d . . . . .
F52 F 0.7315(2) 0.3227(2) 0.56130(7) 0.0383(6) Uani 1 1 d . . . . .
F51 F 0.6955(2) 0.4902(2) 0.54771(7) 0.0390(6) Uani 1 1 d . . . . .
F64 F 0.1199(2) 0.50271(19) 0.67421(8) 0.0395(6) Uani 1 1 d . . . . .
F32 F 1.3445(2) 1.0172(2) 0.67566(8) 0.0431(6) Uani 1 1 d . . . . .
O53 O 0.9104(3) 0.5049(2) 0.72846(8) 0.0276(6) Uani 1 1 d . . . . .
O21 O 0.5762(3) 1.0024(2) 0.72295(8) 0.0283(6) Uani 1 1 d . . . . .
N41 N 0.5864(3) 0.1903(2) 0.67234(10) 0.0281(7) Uani 1 1 d . . . . .
H41 H 0.559981 0.128247 0.680373 0.034 Uiso 1 1 calc R U . . .
N63 N 0.5749(3) 0.6999(2) 0.63930(10) 0.0296(7) Uani 1 1 d . . . . .
H63 H 0.606003 0.763490 0.643386 0.036 Uiso 1 1 calc R U . . .
N23 N 0.8977(3) 1.1880(2) 0.62021(10) 0.0297(7) Uani 1 1 d . . . . .
H23 H 0.865835 1.252394 0.619938 0.036 Uiso 1 1 calc R U . . .
N1 N 0.9194(3) 0.6886(3) 0.67719(10) 0.0272(7) Uani 1 1 d . . . . .
C35 C 0.6901(4) 0.3513(3) 0.66838(11) 0.0224(8) Uani 1 1 d . . . . .
C4 C 0.8099(4) 0.8443(3) 0.66899(11) 0.0227(7) Uani 1 1 d . . . . .
C34 C 0.6086(4) 0.3375(3) 0.63513(11) 0.0250(8) Uani 1 1 d . . . . .
C17 C 0.9696(4) 0.8504(3) 0.56823(12) 0.0280(8) Uani 1 1 d . . . . .
C37 C 0.8371(4) 0.4184(3) 0.71608(11) 0.0248(8) Uani 1 1 d . . . . .
C9 C 0.8315(4) 0.7574(3) 0.69438(11) 0.0250(8) Uani 1 1 d . . . . .
C27 C 1.1449(4) 0.9977(3) 0.64410(12) 0.0280(8) Uani 1 1 d . . . . .
H27 H 1.160375 0.924073 0.640818 0.034 Uiso 1 1 calc R U . . .
C36 C 0.7719(4) 0.4339(3) 0.68198(11) 0.0240(8) Uani 1 1 d . . . . .
H36 H 0.782028 0.497876 0.668273 0.029 Uiso 1 1 calc R U . . .
C26 C 1.0304(4) 1.0468(3) 0.63043(11) 0.0238(8) Uani 1 1 d . . . . .
C57 C 0.4431(4) 0.5555(3) 0.63882(11) 0.0234(8) Uani 1 1 d . . . . .
C3 C 0.8850(4) 0.8233(3) 0.63519(12) 0.0249(8) Uani 1 1 d . . . . .
C8 C 0.7674(4) 0.7490(3) 0.72912(12) 0.0276(8) Uani 1 1 d . . . . .
H8 H 0.782948 0.690881 0.745406 0.033 Uiso 1 1 calc R U . . .
C40 C 0.6743(4) 0.2563(3) 0.69073(11) 0.0257(8) Uani 1 1 d . . . . .
C6 C 0.6596(4) 0.9180(3) 0.71423(11) 0.0243(8) Uani 1 1 d . . . . .
C2 C 0.9490(4) 0.7275(3) 0.64180(12) 0.0269(8) Uani 1 1 d . . . . .
H2 H 1.004722 0.693959 0.624568 0.032 Uiso 1 1 calc R U . . .
C62 C 0.4563(4) 0.6641(3) 0.65182(12) 0.0268(8) Uani 1 1 d . . . . .
C5 C 0.7222(4) 0.9265(3) 0.67969(12) 0.0248(8) Uani 1 1 d . . . . .
H5 H 0.706985 0.985343 0.663704 0.030 Uiso 1 1 calc R U . . .
C56 C 0.5590(4) 0.5290(3) 0.61878(11) 0.0239(8) Uani 1 1 d . . . . .
C58 C 0.3281(4) 0.4995(3) 0.64705(11) 0.0265(8) Uani 1 1 d . . . . .
H58 H 0.316106 0.427992 0.639480 0.032 Uiso 1 1 calc R U . . .
C10 C 0.8804(4) 0.8941(3) 0.59935(11) 0.0248(8) Uani 1 1 d . . . . .
C25 C 0.9177(4) 1.0099(3) 0.60991(11) 0.0247(8) Uani 1 1 d . . . . .
C7 C 0.6797(4) 0.8293(3) 0.73891(12) 0.0273(8) Uani 1 1 d . . . . .
H7 H 0.634097 0.824736 0.761775 0.033 Uiso 1 1 calc R U . . .
C44 C 0.3821(4) 0.3523(3) 0.56142(12) 0.0311(9) Uani 1 1 d . . . . .
C49 C 0.7065(4) 0.4199(3) 0.57686(12) 0.0303(9) Uani 1 1 d . . . . .
C59 C 0.2346(4) 0.5546(3) 0.66667(12) 0.0285(9) Uani 1 1 d . . . . .
C11 C 0.7471(4) 0.8909(3) 0.58355(12) 0.0283(9) Uani 1 1 d . . . . .
C38 C 0.8245(4) 0.3220(3) 0.73708(12) 0.0292(8) Uani 1 1 d . . . . .
H38 H 0.871594 0.312602 0.759488 0.035 Uiso 1 1 calc R U . . .
C33 C 0.5481(4) 0.2395(3) 0.63933(12) 0.0277(8) Uani 1 1 d . . . . .
H33 H 0.489036 0.210495 0.622045 0.033 Uiso 1 1 calc R U . . .
C42 C 0.5875(4) 0.4175(3) 0.60244(11) 0.0260(8) Uani 1 1 d . . . . .
C60 C 0.2474(4) 0.6607(3) 0.67958(13) 0.0326(9) Uani 1 1 d . . . . .
H60 H 0.180041 0.693603 0.692914 0.039 Uiso 1 1 calc R U . . .
C31 C 1.0127(4) 1.1590(3) 0.63660(12) 0.0271(8) Uani 1 1 d . . . . .
C24 C 0.8415(4) 1.0987(3) 0.60430(13) 0.0300(9) Uani 1 1 d . . . . .
H24 H 0.762464 1.098494 0.591483 0.036 Uiso 1 1 calc R U . . .
C39 C 0.7419(4) 0.2409(3) 0.72449(12) 0.0297(9) Uani 1 1 d . . . . .
H39 H 0.732042 0.177344 0.738464 0.036 Uiso 1 1 calc R U . . .
C12 C 0.6399(4) 0.8845(3) 0.57035(12) 0.0289(9) Uani 1 1 d . . . . .
C22 C 0.4948(4) 0.9926(4) 0.75555(12) 0.0323(9) Uani 1 1 d . . . . .
H22A H 0.442866 0.928408 0.753287 0.049 Uiso 1 1 calc R U . . .
H22B H 0.439224 1.054854 0.757228 0.049 Uiso 1 1 calc R U . . .
H22C H 0.547262 0.988033 0.778147 0.049 Uiso 1 1 calc R U . . .
C55 C 0.6363(4) 0.6199(3) 0.61941(12) 0.0298(9) Uani 1 1 d . . . . .
H55 H 0.717546 0.625833 0.608068 0.036 Uiso 1 1 calc R U . . .
C43 C 0.4764(4) 0.3812(3) 0.57865(12) 0.0292(9) Uani 1 1 d . . . . .
C30 C 1.1033(4) 1.2225(3) 0.65588(12) 0.0333(9) Uani 1 1 d . . . . .
H30 H 1.088666 1.295936 0.659938 0.040 Uiso 1 1 calc R U . . .
C61 C 0.3604(4) 0.7165(3) 0.67248(13) 0.0319(9) Uani 1 1 d . . . . .
H61 H 0.371895 0.786990 0.681245 0.038 Uiso 1 1 calc R U . . .
C13 C 0.5085(4) 0.8809(3) 0.55421(12) 0.0316(9) Uani 1 1 d . . . . .
C28 C 1.2318(4) 1.0628(3) 0.66230(12) 0.0326(9) Uani 1 1 d . . . . .
C47 C 0.2812(5) 0.3594(4) 0.49894(13) 0.0418(11) Uani 1 1 d . . . . .
H47A H 0.293039 0.436554 0.498498 0.063 Uiso 1 1 calc R U . . .
H47B H 0.205100 0.340784 0.484578 0.063 Uiso 1 1 calc R U . . .
H47C H 0.355534 0.324835 0.487814 0.063 Uiso 1 1 calc R U . . .
C54 C 1.0013(4) 0.4878(3) 0.75856(12) 0.0325(9) Uani 1 1 d . . . . .
H54A H 1.058147 0.429170 0.751887 0.049 Uiso 1 1 calc R U . . .
H54B H 0.955739 0.470235 0.781657 0.049 Uiso 1 1 calc R U . . .
H54C H 1.051361 0.552472 0.762393 0.049 Uiso 1 1 calc R U . . .
C45 C 0.2652(4) 0.3216(3) 0.54011(13) 0.0347(10) Uani 1 1 d . . . . .
C29 C 1.2146(4) 1.1738(3) 0.66871(13) 0.0350(10) Uani 1 1 d . . . . .
H29 H 1.277649 1.213763 0.681445 0.042 Uiso 1 1 calc R U . . .
C15 C 0.4147(4) 0.9319(4) 0.58248(14) 0.0433(11) Uani 1 1 d . . . . .
H15A H 0.415316 0.891088 0.605837 0.065 Uiso 1 1 calc R U . . .
H15B H 0.328877 0.931592 0.571871 0.065 Uiso 1 1 calc R U . . .
H15C H 0.440758 1.005101 0.587602 0.065 Uiso 1 1 calc R U . . .
C48 C 0.1476(5) 0.3754(4) 0.55842(14) 0.0426(11) Uani 1 1 d . . . . .
H48A H 0.137833 0.349601 0.584138 0.064 Uiso 1 1 calc R U . . .
H48B H 0.071279 0.357968 0.543974 0.064 Uiso 1 1 calc R U . . .
H48C H 0.159667 0.452486 0.558689 0.064 Uiso 1 1 calc R U . . .
C16 C 0.5057(5) 0.9445(4) 0.51647(15) 0.0458(12) Uani 1 1 d . . . . .
H16A H 0.528899 1.018580 0.521202 0.069 Uiso 1 1 calc R U . . .
H16B H 0.420043 0.941500 0.505759 0.069 Uiso 1 1 calc R U . . .
H16C H 0.566360 0.913072 0.498858 0.069 Uiso 1 1 calc R U . . .
C14 C 0.4675(5) 0.7628(4) 0.54609(15) 0.0456(12) Uani 1 1 d . . . . .
H14A H 0.528808 0.730015 0.528988 0.068 Uiso 1 1 calc R U . . .
H14B H 0.382973 0.762183 0.534612 0.068 Uiso 1 1 calc R U . . .
H14C H 0.465356 0.722902 0.569615 0.068 Uiso 1 1 calc R U . . .
C46 C 0.2487(6) 0.1980(4) 0.54148(17) 0.0533(14) Uani 1 1 d . . . . .
H46A H 0.321995 0.163997 0.529553 0.080 Uiso 1 1 calc R U . . .
H46B H 0.170956 0.177975 0.528144 0.080 Uiso 1 1 calc R U . . .
H46C H 0.242814 0.174781 0.567601 0.080 Uiso 1 1 calc R U . . .
H1 H 0.945(4) 0.626(3) 0.6864(12) 0.023(10) Uiso 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
F18 C17 1.347(4) . ?
F50 C49 1.352(5) . ?
F20 C17 1.346(4) . ?
F19 C17 1.338(5) . ?
F52 C49 1.344(5) . ?
F51 C49 1.344(5) . ?
F64 C59 1.371(4) . ?
F32 C28 1.373(5) . ?
O53 C37 1.378(4) . ?
O53 C54 1.426(5) . ?
O21 C6 1.386(4) . ?
O21 C22 1.422(5) . ?
N41 H41 0.8600 . ?
N41 C40 1.378(5) . ?
N41 C33 1.364(5) . ?
N63 H63 0.8600 . ?
N63 C62 1.372(5) . ?
N63 C55 1.364(5) . ?
N23 H23 0.8600 . ?
N23 C31 1.365(5) . ?
N23 C24 1.365(5) . ?
N1 C9 1.380(5) . ?
N1 C2 1.363(5) . ?
N1 H1 0.88(4) . ?
C35 C34 1.446(5) . ?
C35 C36 1.406(5) . ?
C35 C40 1.420(5) . ?
C4 C9 1.411(5) . ?
C4 C3 1.437(5) . ?
C4 C5 1.411(5) . ?
C34 C33 1.369(5) . ?
C34 C42 1.527(5) . ?
C17 C10 1.524(6) . ?
C37 C36 1.383(6) . ?
C37 C38 1.404(5) . ?
C9 C8 1.388(6) . ?
C27 H27 0.9300 . ?
C27 C26 1.410(5) . ?
C27 C28 1.362(6) . ?
C36 H36 0.9300 . ?
C26 C25 1.441(5) . ?
C26 C31 1.415(5) . ?
C57 C62 1.422(5) . ?
C57 C56 1.423(5) . ?
C57 C58 1.403(5) . ?
C3 C2 1.375(5) . ?
C3 C10 1.529(5) . ?
C8 H8 0.9300 . ?
C8 C7 1.385(6) . ?
C40 C39 1.385(6) . ?
C6 C5 1.374(6) . ?
C6 C7 1.410(5) . ?
C2 H2 0.9300 . ?
C62 C61 1.386(6) . ?
C5 H5 0.9300 . ?
C56 C42 1.520(5) . ?
C56 C55 1.376(5) . ?
C58 H58 0.9300 . ?
C58 C59 1.365(5) . ?
C10 C25 1.525(5) . ?
C10 C11 1.483(5) . ?
C25 C24 1.364(5) . ?
C7 H7 0.9300 . ?
C44 C43 1.198(6) . ?
C44 C45 1.467(6) . ?
C49 C42 1.519(5) . ?
C59 C60 1.392(5) . ?
C11 C12 1.200(6) . ?
C38 H38 0.9300 . ?
C38 C39 1.387(6) . ?
C33 H33 0.9300 . ?
C42 C43 1.485(6) . ?
C60 H60 0.9300 . ?
C60 C61 1.376(6) . ?
C31 C30 1.393(6) . ?
C24 H24 0.9300 . ?
C39 H39 0.9300 . ?
C12 C13 1.468(6) . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C55 H55 0.9300 . ?
C30 H30 0.9300 . ?
C30 C29 1.372(6) . ?
C61 H61 0.9300 . ?
C13 C15 1.520(6) . ?
C13 C16 1.537(6) . ?
C13 C14 1.545(6) . ?
C28 C29 1.400(6) . ?
C47 H47A 0.9600 . ?
C47 H47B 0.9600 . ?
C47 H47C 0.9600 . ?
C47 C45 1.524(7) . ?
C54 H54A 0.9600 . ?
C54 H54B 0.9600 . ?
C54 H54C 0.9600 . ?
C45 C48 1.524(7) . ?
C45 C46 1.536(6) . ?
C29 H29 0.9300 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C48 H48A 0.9600 . ?
C48 H48B 0.9600 . ?
C48 H48C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C46 H46A 0.9600 . ?
C46 H46B 0.9600 . ?
C46 H46C 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
C37 O53 C54 118.5(3) . . ?
C6 O21 C22 118.6(3) . . ?
C40 N41 H41 125.6 . . ?
C33 N41 H41 125.6 . . ?
C33 N41 C40 108.8(3) . . ?
C62 N63 H63 125.0 . . ?
C55 N63 H63 125.0 . . ?
C55 N63 C62 110.1(3) . . ?
C31 N23 H23 125.4 . . ?
C31 N23 C24 109.2(3) . . ?
C24 N23 H23 125.4 . . ?
C9 N1 H1 125(3) . . ?
C2 N1 C9 109.0(3) . . ?
C2 N1 H1 125(3) . . ?
C36 C35 C34 135.0(3) . . ?
C36 C35 C40 118.8(3) . . ?
C40 C35 C34 106.2(3) . . ?
C9 C4 C3 107.2(3) . . ?
C5 C4 C9 118.8(4) . . ?
C5 C4 C3 133.9(3) . . ?
C35 C34 C42 127.5(3) . . ?
C33 C34 C35 106.5(3) . . ?
C33 C34 C42 126.0(4) . . ?
F18 C17 C10 112.4(3) . . ?
F20 C17 F18 106.0(3) . . ?
F20 C17 C10 112.9(3) . . ?
F19 C17 F18 106.6(3) . . ?
F19 C17 F20 106.7(3) . . ?
F19 C17 C10 111.8(3) . . ?
O53 C37 C36 115.5(3) . . ?
O53 C37 C38 122.9(3) . . ?
C36 C37 C38 121.6(4) . . ?
N1 C9 C4 107.3(3) . . ?
N1 C9 C8 130.4(4) . . ?
C8 C9 C4 122.2(4) . . ?
C26 C27 H27 121.4 . . ?
C28 C27 H27 121.4 . . ?
C28 C27 C26 117.1(4) . . ?
C35 C36 H36 120.5 . . ?
C37 C36 C35 118.9(3) . . ?
C37 C36 H36 120.5 . . ?
C27 C26 C25 135.1(3) . . ?
C27 C26 C31 118.5(4) . . ?
C31 C26 C25 106.4(3) . . ?
C62 C57 C56 107.1(3) . . ?
C58 C57 C62 118.7(3) . . ?
C58 C57 C56 134.2(3) . . ?
C4 C3 C10 123.7(3) . . ?
C2 C3 C4 106.0(3) . . ?
C2 C3 C10 130.1(4) . . ?
C9 C8 H8 120.9 . . ?
C7 C8 C9 118.3(4) . . ?
C7 C8 H8 120.9 . . ?
N41 C40 C35 107.9(3) . . ?
N41 C40 C39 130.4(3) . . ?
C39 C40 C35 121.7(4) . . ?
O21 C6 C7 122.7(3) . . ?
C5 C6 O21 115.3(3) . . ?
C5 C6 C7 122.0(3) . . ?
N1 C2 C3 110.4(4) . . ?
N1 C2 H2 124.8 . . ?
C3 C2 H2 124.8 . . ?
N63 C62 C57 106.7(3) . . ?
N63 C62 C61 130.7(3) . . ?
C61 C62 C57 122.6(4) . . ?
C4 C5 H5 120.7 . . ?
C6 C5 C4 118.6(3) . . ?
C6 C5 H5 120.7 . . ?
C57 C56 C42 123.8(3) . . ?
C55 C56 C57 106.9(3) . . ?
C55 C56 C42 129.2(4) . . ?
C57 C58 H58 121.5 . . ?
C59 C58 C57 117.0(3) . . ?
C59 C58 H58 121.5 . . ?
C17 C10 C3 111.4(3) . . ?
C17 C10 C25 110.7(3) . . ?
C25 C10 C3 109.2(3) . . ?
C11 C10 C17 106.5(3) . . ?
C11 C10 C3 108.6(3) . . ?
C11 C10 C25 110.4(3) . . ?
C26 C25 C10 128.3(3) . . ?
C24 C25 C26 106.4(3) . . ?
C24 C25 C10 125.0(3) . . ?
C8 C7 C6 120.0(4) . . ?
C8 C7 H7 120.0 . . ?
C6 C7 H7 120.0 . . ?
C43 C44 C45 177.7(4) . . ?
F50 C49 C42 112.7(3) . . ?
F52 C49 F50 105.5(3) . . ?
F52 C49 C42 112.1(3) . . ?
F51 C49 F50 106.4(3) . . ?
F51 C49 F52 106.6(3) . . ?
F51 C49 C42 113.1(3) . . ?
F64 C59 C60 117.3(4) . . ?
C58 C59 F64 118.3(3) . . ?
C58 C59 C60 124.4(4) . . ?
C12 C11 C10 177.6(4) . . ?
C37 C38 H38 119.9 . . ?
C39 C38 C37 120.2(4) . . ?
C39 C38 H38 119.9 . . ?
N41 C33 C34 110.7(4) . . ?
N41 C33 H33 124.7 . . ?
C34 C33 H33 124.7 . . ?
C56 C42 C34 109.4(3) . . ?
C49 C42 C34 109.9(3) . . ?
C49 C42 C56 111.1(3) . . ?
C43 C42 C34 109.5(3) . . ?
C43 C42 C56 109.6(3) . . ?
C43 C42 C49 107.4(3) . . ?
C59 C60 H60 120.2 . . ?
C61 C60 C59 119.5(4) . . ?
C61 C60 H60 120.2 . . ?
N23 C31 C26 107.8(3) . . ?
N23 C31 C30 129.7(4) . . ?
C30 C31 C26 122.6(4) . . ?
N23 C24 H24 124.9 . . ?
C25 C24 N23 110.3(4) . . ?
C25 C24 H24 124.9 . . ?
C40 C39 C38 118.8(4) . . ?
C40 C39 H39 120.6 . . ?
C38 C39 H39 120.6 . . ?
C11 C12 C13 178.0(4) . . ?
O21 C22 H22A 109.5 . . ?
O21 C22 H22B 109.5 . . ?
O21 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
N63 C55 C56 109.3(4) . . ?
N63 C55 H55 125.4 . . ?
C56 C55 H55 125.4 . . ?
C44 C43 C42 176.0(4) . . ?
C31 C30 H30 120.9 . . ?
C29 C30 C31 118.2(4) . . ?
C29 C30 H30 120.9 . . ?
C62 C61 H61 121.2 . . ?
C60 C61 C62 117.7(3) . . ?
C60 C61 H61 121.2 . . ?
C12 C13 C15 108.9(4) . . ?
C12 C13 C16 109.4(4) . . ?
C12 C13 C14 110.6(4) . . ?
C15 C13 C16 109.7(4) . . ?
C15 C13 C14 109.7(4) . . ?
C16 C13 C14 108.6(4) . . ?
F32 C28 C29 117.0(4) . . ?
C27 C28 F32 118.3(4) . . ?
C27 C28 C29 124.7(4) . . ?
H47A C47 H47B 109.5 . . ?
H47A C47 H47C 109.5 . . ?
H47B C47 H47C 109.5 . . ?
C45 C47 H47A 109.5 . . ?
C45 C47 H47B 109.5 . . ?
C45 C47 H47C 109.5 . . ?
O53 C54 H54A 109.5 . . ?
O53 C54 H54B 109.5 . . ?
O53 C54 H54C 109.5 . . ?
H54A C54 H54B 109.5 . . ?
H54A C54 H54C 109.5 . . ?
H54B C54 H54C 109.5 . . ?
C44 C45 C47 108.2(4) . . ?
C44 C45 C48 109.1(4) . . ?
C44 C45 C46 109.4(4) . . ?
C47 C45 C48 110.5(4) . . ?
C47 C45 C46 110.3(4) . . ?
C48 C45 C46 109.4(4) . . ?
C30 C29 C28 118.9(4) . . ?
C30 C29 H29 120.6 . . ?
C28 C29 H29 120.6 . . ?
C13 C15 H15A 109.5 . . ?
C13 C15 H15B 109.5 . . ?
C13 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C45 C48 H48A 109.5 . . ?
C45 C48 H48B 109.5 . . ?
C45 C48 H48C 109.5 . . ?
H48A C48 H48B 109.5 . . ?
H48A C48 H48C 109.5 . . ?
H48B C48 H48C 109.5 . . ?
C13 C16 H16A 109.5 . . ?
C13 C16 H16B 109.5 . . ?
C13 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C45 C46 H46A 109.5 . . ?
C45 C46 H46B 109.5 . . ?
C45 C46 H46C 109.5 . . ?
H46A C46 H46B 109.5 . . ?
H46A C46 H46C 109.5 . . ?
H46B C46 H46C 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
F18 C17 C10 C3 61.2(4) . . . . ?
F18 C17 C10 C25 -177.1(3) . . . . ?
F18 C17 C10 C11 -57.1(4) . . . . ?
F50 C49 C42 C34 -58.3(4) . . . . ?
F50 C49 C42 C56 62.8(4) . . . . ?
F50 C49 C42 C43 -177.4(3) . . . . ?
F20 C17 C10 C3 -58.7(4) . . . . ?
F20 C17 C10 C25 63.0(4) . . . . ?
F20 C17 C10 C11 -177.0(3) . . . . ?
F19 C17 C10 C3 -179.0(3) . . . . ?
F19 C17 C10 C25 -57.3(4) . . . . ?
F19 C17 C10 C11 62.7(4) . . . . ?
F52 C49 C42 C34 60.5(4) . . . . ?
F52 C49 C42 C56 -178.4(3) . . . . ?
F52 C49 C42 C43 -58.6(4) . . . . ?
F51 C49 C42 C34 -179.0(3) . . . . ?
F51 C49 C42 C56 -57.9(4) . . . . ?
F51 C49 C42 C43 61.9(4) . . . . ?
F64 C59 C60 C61 -179.5(4) . . . . ?
F32 C28 C29 C30 -179.9(4) . . . . ?
O53 C37 C36 C35 -176.9(3) . . . . ?
O53 C37 C38 C39 175.3(4) . . . . ?
O21 C6 C5 C4 179.3(3) . . . . ?
O21 C6 C7 C8 -178.0(4) . . . . ?
N41 C40 C39 C38 -179.2(4) . . . . ?
N63 C62 C61 C60 177.2(4) . . . . ?
N23 C31 C30 C29 -177.8(4) . . . . ?
N1 C9 C8 C7 -177.8(4) . . . . ?
C35 C34 C33 N41 -0.7(4) . . . . ?
C35 C34 C42 C56 -48.1(5) . . . . ?
C35 C34 C42 C49 74.1(5) . . . . ?
C35 C34 C42 C43 -168.2(4) . . . . ?
C35 C40 C39 C38 1.6(6) . . . . ?
C4 C9 C8 C7 -0.2(6) . . . . ?
C4 C3 C2 N1 -0.4(4) . . . . ?
C4 C3 C10 C17 -179.4(3) . . . . ?
C4 C3 C10 C25 58.1(5) . . . . ?
C4 C3 C10 C11 -62.4(5) . . . . ?
C34 C35 C36 C37 -179.9(4) . . . . ?
C34 C35 C40 N41 -1.2(4) . . . . ?
C34 C35 C40 C39 178.2(4) . . . . ?
C17 C10 C25 C26 -71.1(5) . . . . ?
C17 C10 C25 C24 115.3(4) . . . . ?
C37 C38 C39 C40 1.0(6) . . . . ?
C9 N1 C2 C3 1.6(4) . . . . ?
C9 C4 C3 C2 -0.9(4) . . . . ?
C9 C4 C3 C10 175.2(3) . . . . ?
C9 C4 C5 C6 -1.0(5) . . . . ?
C9 C8 C7 C6 -1.4(6) . . . . ?
C27 C26 C25 C10 7.0(7) . . . . ?
C27 C26 C25 C24 -178.5(4) . . . . ?
C27 C26 C31 N23 178.6(3) . . . . ?
C27 C26 C31 C30 -0.5(6) . . . . ?
C27 C28 C29 C30 -0.3(7) . . . . ?
C36 C35 C34 C33 -177.3(4) . . . . ?
C36 C35 C34 C42 0.0(7) . . . . ?
C36 C35 C40 N41 177.5(3) . . . . ?
C36 C35 C40 C39 -3.1(6) . . . . ?
C36 C37 C38 C39 -2.2(6) . . . . ?
C26 C27 C28 F32 -179.6(4) . . . . ?
C26 C27 C28 C29 0.8(7) . . . . ?
C26 C25 C24 N23 -0.7(5) . . . . ?
C26 C31 C30 C29 1.1(6) . . . . ?
C57 C62 C61 C60 -1.6(6) . . . . ?
C57 C56 C42 C34 -68.6(5) . . . . ?
C57 C56 C42 C49 169.9(4) . . . . ?
C57 C56 C42 C43 51.5(5) . . . . ?
C57 C56 C55 N63 1.0(5) . . . . ?
C57 C58 C59 F64 178.3(3) . . . . ?
C57 C58 C59 C60 -1.5(6) . . . . ?
C3 C4 C9 N1 1.9(4) . . . . ?
C3 C4 C9 C8 -176.2(4) . . . . ?
C3 C4 C5 C6 175.9(4) . . . . ?
C3 C10 C25 C26 51.9(5) . . . . ?
C3 C10 C25 C24 -121.7(4) . . . . ?
C40 N41 C33 C34 0.0(5) . . . . ?
C40 C35 C34 C33 1.1(4) . . . . ?
C40 C35 C34 C42 178.4(4) . . . . ?
C40 C35 C36 C37 1.9(5) . . . . ?
C2 N1 C9 C4 -2.1(4) . . . . ?
C2 N1 C9 C8 175.8(4) . . . . ?
C2 C3 C10 C17 -4.3(6) . . . . ?
C2 C3 C10 C25 -126.8(4) . . . . ?
C2 C3 C10 C11 112.7(4) . . . . ?
C62 N63 C55 C56 -0.5(5) . . . . ?
C62 C57 C56 C42 176.0(3) . . . . ?
C62 C57 C56 C55 -1.1(4) . . . . ?
C62 C57 C58 C59 1.2(6) . . . . ?
C5 C4 C9 N1 179.5(3) . . . . ?
C5 C4 C9 C8 1.4(6) . . . . ?
C5 C4 C3 C2 -178.1(4) . . . . ?
C5 C4 C3 C10 -2.0(7) . . . . ?
C5 C6 C7 C8 1.9(6) . . . . ?
C56 C57 C62 N63 0.8(4) . . . . ?
C56 C57 C62 C61 179.8(4) . . . . ?
C56 C57 C58 C59 -178.1(4) . . . . ?
C58 C57 C62 N63 -178.7(3) . . . . ?
C58 C57 C62 C61 0.4(6) . . . . ?
C58 C57 C56 C42 -4.7(7) . . . . ?
C58 C57 C56 C55 178.2(4) . . . . ?
C58 C59 C60 C61 0.3(7) . . . . ?
C10 C3 C2 N1 -176.1(4) . . . . ?
C10 C25 C24 N23 174.1(4) . . . . ?
C25 C26 C31 N23 -1.0(4) . . . . ?
C25 C26 C31 C30 179.8(4) . . . . ?
C7 C6 C5 C4 -0.6(6) . . . . ?
C59 C60 C61 C62 1.3(6) . . . . ?
C11 C10 C25 C26 171.3(4) . . . . ?
C11 C10 C25 C24 -2.4(6) . . . . ?
C38 C37 C36 C35 0.7(6) . . . . ?
C33 N41 C40 C35 0.8(4) . . . . ?
C33 N41 C40 C39 -178.5(4) . . . . ?
C33 C34 C42 C56 128.7(4) . . . . ?
C33 C34 C42 C49 -109.1(4) . . . . ?
C33 C34 C42 C43 8.6(5) . . . . ?
C42 C34 C33 N41 -178.1(3) . . . . ?
C42 C56 C55 N63 -175.9(4) . . . . ?
C31 N23 C24 C25 0.0(5) . . . . ?
C31 C26 C25 C10 -173.5(4) . . . . ?
C31 C26 C25 C24 1.1(4) . . . . ?
C31 C30 C29 C28 -0.7(6) . . . . ?
C24 N23 C31 C26 0.6(5) . . . . ?
C24 N23 C31 C30 179.7(4) . . . . ?
C22 O21 C6 C5 171.5(3) . . . . ?
C22 O21 C6 C7 -8.6(5) . . . . ?
C55 N63 C62 C57 -0.2(4) . . . . ?
C55 N63 C62 C61 -179.1(4) . . . . ?
C55 C56 C42 C34 107.8(5) . . . . ?
C55 C56 C42 C49 -13.7(6) . . . . ?
C55 C56 C42 C43 -132.1(4) . . . . ?
C28 C27 C26 C25 179.1(4) . . . . ?
C28 C27 C26 C31 -0.4(6) . . . . ?
C54 O53 C37 C36 -166.8(3) . . . . ?
C54 O53 C37 C38 15.7(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 3.925
_oxdiff_exptl_absorpt_empirical_full_min 0.310
