# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2021

####################################################################### 
# 
# 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_bdc-20191031
_database_code_depnum_ccdc_archive 'CCDC 1962621'
loop_
_audit_author_name
_audit_author_address
jacs
;htu
China
;
_audit_update_record             
;
2019-10-31 deposited with the CCDC.	2021-04-08 downloaded from the CCDC.
;
_audit_creation_date             2019-10-31
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2018.12.18 svn.r3554 for Rigaku Oxford Diffraction, GUI svn.r1)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C47 H39 F3 Ni O P2'
_chemical_formula_sum            'C47 H39 F3 Ni O P2'
_chemical_formula_weight         797.43
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_formula         'Ni1 C1 H1 O1 P1 F1'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 '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 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ni Ni 0.3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 '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           29
_space_group_name_H-M_alt        'P c a 21'
_space_group_name_Hall           'P 2c -2ac'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y, z'
'-x+1/2, y, z+1/2'

_cell_length_a                   28.4714(13)
_cell_length_b                   11.5708(5)
_cell_length_c                   12.0356(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3965.0(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5996
_cell_measurement_temperature    284(1)
_cell_measurement_theta_max      26.6450
_cell_measurement_theta_min      3.7970
_shelx_estimated_absorpt_T_max   0.860
_shelx_estimated_absorpt_T_min   0.826
_exptl_absorpt_coefficient_mu    0.620
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.79052
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light red'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.336
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1656
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.25
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0340
_diffrn_reflns_av_unetI/netI     0.0486
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.897
_diffrn_reflns_limit_h_max       37
_diffrn_reflns_limit_h_min       -38
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            20527
_diffrn_reflns_point_group_measured_fraction_full 0.893
_diffrn_reflns_point_group_measured_fraction_max 0.770
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.043
_diffrn_reflns_theta_min         3.325
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      284(1)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0521
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.897
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -29.00  -4.00   1.00    7.53    --   16.29 -75.00 169.00   25
  2  ω    -67.00 -24.00   1.00    7.53    --  -16.91 -60.00 -64.00   43
  3  ω    -24.00   7.00   1.00    7.53    --  -16.91 -88.00  65.00   31
  4  ω     35.00  85.00   1.00    7.53    --   16.29 178.00-120.00   50
  5  ω      6.00  31.00   1.00    7.53    --   16.29  57.00-180.00   25
  6  ω     57.00  85.00   1.00    7.53    --   16.29   0.00-120.00   28
  7  ω     36.00  88.00   1.00    7.53    --   16.29 178.00 120.00   52
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0176725000
_diffrn_orient_matrix_UB_12      -0.0315790000
_diffrn_orient_matrix_UB_13      0.0283078000
_diffrn_orient_matrix_UB_21      0.0016651000
_diffrn_orient_matrix_UB_22      0.0446942000
_diffrn_orient_matrix_UB_23      0.0401418000
_diffrn_orient_matrix_UB_31      -0.0174843000
_diffrn_orient_matrix_UB_32      -0.0276336000
_diffrn_orient_matrix_UB_33      0.0325835000
_diffrn_oxdiff_digest_frames     
;
01488b62b7f3ea7bbf64595684522793600026861f5
;
_diffrn_oxdiff_digest_hkl        
;
0137d0ba2e79076457c2e6aa938be9f70188c2
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.641
_reflns_Friedel_fraction_full    0.776
_reflns_Friedel_fraction_max     0.631
_reflns_number_gt                6960
_reflns_number_total             8151
_reflns_odcompleteness_completeness 99.58
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.346
_refine_diff_density_min         -0.234
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details 
;
 Flack x determined using 2326 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.002(7)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     488
_refine_ls_number_reflns         8151
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0498
_refine_ls_R_factor_gt           0.0380
_refine_ls_restrained_S_all      1.033
_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)+(0.0295P)²+0.1117P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0691
_refine_ls_wR_factor_ref         0.0752
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C47(H47), C48(H48)
2.b Aromatic/amide H refined with riding coordinates:
 C29(H29), C14(H14), C13(H13), C33(H33), C45(H45), C44(H44), C19(H19),
 C22(H22), C20(H20), C7(H7), C32(H32), C39(H39), C18(H18), C16(H16), C31(H31),
 C41(H41), C26(H26), C10(H10), C3(H3), C37(H37), C30(H30), C38(H38), C36(H36),
 C12(H12), C17(H17), C35(H35), C6(H6), C24(H24), C11(H11), C42(H42), C25(H25),
 C23(H23), C5(H5), C4(H4)
2.c Idealised Me refined as rotating group:
 C54(H54A,H54B,H54C)
;
_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
Ni1 Ni 0.60083(2) 0.34441(3) 0.58782(4) 0.02857(10) Uani 1 1 d . . . . .
P8 P 0.65181(3) 0.20908(8) 0.54577(8) 0.0329(2) Uani 1 1 d . . . . .
P27 P 0.61557(3) 0.50501(8) 0.49435(8) 0.03209(19) Uani 1 1 d . . . . .
F50 F 0.49979(9) 0.2451(2) 0.5570(2) 0.0727(8) Uani 1 1 d . . . . .
F52 F 0.48284(9) 0.1883(2) 0.7194(2) 0.0804(9) Uani 1 1 d . . . . .
O53 O 0.61332(10) 0.4008(2) 0.8304(2) 0.0574(8) Uani 1 1 d . . . . .
F51 F 0.53074(9) 0.0911(2) 0.6219(2) 0.0750(8) Uani 1 1 d . . . . .
C29 C 0.60386(12) 0.3868(4) 0.2952(3) 0.0408(9) Uani 1 1 d . . . . .
H29 H 0.606381 0.320874 0.339028 0.049 Uiso 1 1 calc R . . . .
C46 C 0.58128(12) 0.4504(3) 0.7802(3) 0.0354(8) Uani 1 1 d . . . . .
C47 C 0.55258(11) 0.3895(3) 0.7001(3) 0.0313(7) Uani 1 1 d . . . . .
H47 H 0.523147 0.424675 0.674903 0.038 Uiso 1 1 calc R . . . .
C40 C 0.57271(12) 0.5753(3) 0.8041(3) 0.0338(8) Uani 1 1 d . . . . .
C14 C 0.72218(13) 0.3232(3) 0.4274(4) 0.0486(10) Uani 1 1 d . . . . .
H14 H 0.699281 0.332152 0.372986 0.058 Uiso 1 1 calc R . . . .
C48 C 0.55810(11) 0.2673(3) 0.6926(3) 0.0339(8) Uani 1 1 d . . . . .
H48 H 0.573700 0.231876 0.756693 0.041 Uiso 1 1 calc R . . . .
C9 C 0.71174(11) 0.2640(3) 0.5240(3) 0.0372(8) Uani 1 1 d . . . . .
C13 C 0.76628(14) 0.3690(4) 0.4113(4) 0.0567(12) Uani 1 1 d . . . . .
H13 H 0.773065 0.407333 0.345315 0.068 Uiso 1 1 calc R . . . .
C28 C 0.60835(12) 0.4934(3) 0.3433(3) 0.0381(8) Uani 1 1 d . . . . .
C49 C 0.51887(14) 0.2003(3) 0.6479(4) 0.0452(10) Uani 1 1 d . . . . .
C33 C 0.60308(15) 0.5910(4) 0.2766(4) 0.0550(11) Uani 1 1 d . . . . .
H33 H 0.604563 0.664271 0.308215 0.066 Uiso 1 1 calc R . . . .
C45 C 0.53057(13) 0.6296(3) 0.7831(3) 0.0404(9) Uani 1 1 d . . . . .
H45 H 0.506067 0.588109 0.751126 0.048 Uiso 1 1 calc R . . . .
C15 C 0.66288(11) 0.1051(3) 0.6571(3) 0.0382(9) Uani 1 1 d . . . . .
C44 C 0.52426(14) 0.7445(4) 0.8087(4) 0.0514(10) Uani 1 1 d . . . . .
H44 H 0.495572 0.779509 0.793602 0.062 Uiso 1 1 calc R . . . .
C34 C 0.57653(13) 0.6287(3) 0.5170(3) 0.0358(8) Uani 1 1 d . . . . .
C2 C 0.64309(12) 0.1157(3) 0.4240(3) 0.0414(9) Uani 1 1 d . . . . .
C19 C 0.67897(15) 0.0782(4) 0.8527(4) 0.0568(12) Uani 1 1 d . . . . .
H19 H 0.680178 0.108450 0.924276 0.068 Uiso 1 1 calc R . . . .
C22 C 0.69481(14) 0.5464(4) 0.6186(3) 0.0524(11) Uani 1 1 d . . . . .
H22 H 0.679819 0.499699 0.670504 0.063 Uiso 1 1 calc R . . . .
C20 C 0.66420(12) 0.1469(3) 0.7656(3) 0.0434(9) Uani 1 1 d . . . . .
H20 H 0.654951 0.222577 0.779654 0.052 Uiso 1 1 calc R . . . .
C21 C 0.67362(13) 0.5689(3) 0.5179(3) 0.0396(9) Uani 1 1 d . . . . .
C7 C 0.59770(13) 0.0901(4) 0.3921(4) 0.0530(11) Uani 1 1 d . . . . .
H7 H 0.572590 0.121225 0.431358 0.064 Uiso 1 1 calc R . . . .
C32 C 0.59565(15) 0.5793(4) 0.1634(4) 0.0618(12) Uani 1 1 d . . . . .
H32 H 0.593089 0.644720 0.118869 0.074 Uiso 1 1 calc R . . . .
C39 C 0.59205(14) 0.7347(3) 0.5550(3) 0.0483(10) Uani 1 1 d . . . . .
H39 H 0.623252 0.743779 0.576103 0.058 Uiso 1 1 calc R . . . .
C18 C 0.69179(16) -0.0339(4) 0.8343(5) 0.0708(15) Uani 1 1 d . . . . .
H18 H 0.702101 -0.079970 0.892666 0.085 Uiso 1 1 calc R . . . .
C16 C 0.67500(14) -0.0091(3) 0.6392(4) 0.0571(12) Uani 1 1 d . . . . .
H16 H 0.673638 -0.039974 0.567933 0.069 Uiso 1 1 calc R . . . .
C43 C 0.56013(15) 0.8091(3) 0.8570(4) 0.0516(10) Uani 1 1 d . . . . .
C31 C 0.59208(14) 0.4716(4) 0.1169(3) 0.0594(12) Uani 1 1 d . . . . .
H31 H 0.587254 0.464088 0.040767 0.071 Uiso 1 1 calc R . . . .
C41 C 0.60836(14) 0.6379(3) 0.8550(3) 0.0473(10) Uani 1 1 d . . . . .
H41 H 0.636627 0.602039 0.872610 0.057 Uiso 1 1 calc R . . . .
C26 C 0.69712(15) 0.6365(4) 0.4420(4) 0.0646(12) Uani 1 1 d . . . . .
H26 H 0.683472 0.652026 0.373437 0.077 Uiso 1 1 calc R . . . .
C10 C 0.74659(12) 0.2518(4) 0.6028(4) 0.0535(10) Uani 1 1 d . . . . .
H10 H 0.740735 0.211007 0.667890 0.064 Uiso 1 1 calc R . . . .
C3 C 0.67943(16) 0.0693(4) 0.3633(4) 0.0664(14) Uani 1 1 d . . . . .
H3 H 0.710249 0.086069 0.383195 0.080 Uiso 1 1 calc R . . . .
C37 C 0.51588(18) 0.8148(4) 0.5283(4) 0.0657(13) Uani 1 1 d . . . . .
H37 H 0.495601 0.877770 0.530339 0.079 Uiso 1 1 calc R . . . .
C30 C 0.59556(13) 0.3755(4) 0.1815(4) 0.0531(11) Uani 1 1 d . . . . .
H30 H 0.592414 0.302543 0.149922 0.064 Uiso 1 1 calc R . . . .
C38 C 0.56156(17) 0.8274(3) 0.5617(4) 0.0648(14) Uani 1 1 d . . . . .
H38 H 0.572044 0.898067 0.588877 0.078 Uiso 1 1 calc R . . . .
C36 C 0.50006(15) 0.7103(4) 0.4920(4) 0.0555(11) Uani 1 1 d . . . . .
H36 H 0.468874 0.702430 0.470297 0.067 Uiso 1 1 calc R . . . .
C12 C 0.80013(15) 0.3591(4) 0.4909(4) 0.0665(13) Uani 1 1 d . . . . .
H12 H 0.829593 0.392095 0.480571 0.080 Uiso 1 1 calc R . . . .
C17 C 0.68927(17) -0.0777(4) 0.7281(5) 0.0741(15) Uani 1 1 d . . . . .
H17 H 0.697225 -0.154577 0.715461 0.089 Uiso 1 1 calc R . . . .
C35 C 0.52960(13) 0.6161(3) 0.4869(3) 0.0445(9) Uani 1 1 d . . . . .
H35 H 0.518278 0.544732 0.463565 0.053 Uiso 1 1 calc R . . . .
C6 C 0.58916(18) 0.0186(5) 0.3024(5) 0.0780(16) Uani 1 1 d . . . . .
H6 H 0.558440 0.001974 0.281595 0.094 Uiso 1 1 calc R . . . .
C24 C 0.76100(17) 0.6607(5) 0.5681(6) 0.0882(18) Uani 1 1 d . . . . .
H24 H 0.790026 0.692751 0.585551 0.106 Uiso 1 1 calc R . . . .
C11 C 0.79008(13) 0.3004(4) 0.5848(5) 0.0715(13) Uani 1 1 d . . . . .
H11 H 0.813181 0.292566 0.638859 0.086 Uiso 1 1 calc R . . . .
C42 C 0.60184(15) 0.7537(4) 0.8795(4) 0.0541(11) Uani 1 1 d . . . . .
H42 H 0.626245 0.795061 0.911944 0.065 Uiso 1 1 calc R . . . .
C25 C 0.7411(2) 0.6817(5) 0.4670(6) 0.0900(19) Uani 1 1 d . . . . .
H25 H 0.756938 0.726239 0.414806 0.108 Uiso 1 1 calc R . . . .
C54 C 0.55415(19) 0.9347(4) 0.8823(5) 0.0792(15) Uani 1 1 d . . . . .
H54A H 0.563635 0.979684 0.819093 0.119 Uiso 1 1 calc GR . . . .
H54B H 0.573192 0.954985 0.945152 0.119 Uiso 1 1 calc GR . . . .
H54C H 0.521768 0.950253 0.898819 0.119 Uiso 1 1 calc GR . . . .
C23 C 0.73863(16) 0.5935(5) 0.6425(5) 0.0778(15) Uani 1 1 d . . . . .
H23 H 0.752635 0.578452 0.710814 0.093 Uiso 1 1 calc R . . . .
C5 C 0.6257(2) -0.0274(5) 0.2443(5) 0.0934(19) Uani 1 1 d . . . . .
H5 H 0.619903 -0.076596 0.184784 0.112 Uiso 1 1 calc R . . . .
C4 C 0.6709(2) -0.0016(5) 0.2734(5) 0.095(2) Uani 1 1 d . . . . .
H4 H 0.695813 -0.031797 0.232702 0.114 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
Ni1 P8 2.1942(9) . ?
Ni1 P27 2.2125(10) . ?
Ni1 C47 1.997(3) . ?
Ni1 C48 1.966(3) . ?
P8 C9 1.839(3) . ?
P8 C15 1.828(4) . ?
P8 C2 1.838(4) . ?
P27 C28 1.834(4) . ?
P27 C34 1.832(3) . ?
P27 C21 1.833(4) . ?
F50 C49 1.327(5) . ?
F52 C49 1.346(4) . ?
O53 C46 1.235(4) . ?
F51 C49 1.346(4) . ?
C29 H29 0.9300 . ?
C29 C28 1.369(5) . ?
C29 C30 1.396(6) . ?
C46 C47 1.447(5) . ?
C46 C40 1.494(5) . ?
C47 H47 0.9800 . ?
C47 C48 1.425(5) . ?
C40 C45 1.378(5) . ?
C40 C41 1.390(5) . ?
C14 H14 0.9300 . ?
C14 C9 1.382(5) . ?
C14 C13 1.377(5) . ?
C48 H48 0.9800 . ?
C48 C49 1.462(5) . ?
C9 C10 1.380(5) . ?
C13 H13 0.9300 . ?
C13 C12 1.363(6) . ?
C28 C33 1.394(5) . ?
C33 H33 0.9300 . ?
C33 C32 1.386(6) . ?
C45 H45 0.9300 . ?
C45 C44 1.376(5) . ?
C15 C20 1.392(5) . ?
C15 C16 1.383(5) . ?
C44 H44 0.9300 . ?
C44 C43 1.393(6) . ?
C34 C39 1.382(5) . ?
C34 C35 1.392(5) . ?
C2 C7 1.381(5) . ?
C2 C3 1.376(5) . ?
C19 H19 0.9300 . ?
C19 C20 1.381(5) . ?
C19 C18 1.365(7) . ?
C22 H22 0.9300 . ?
C22 C21 1.378(5) . ?
C22 C23 1.392(6) . ?
C20 H20 0.9300 . ?
C21 C26 1.376(5) . ?
C7 H7 0.9300 . ?
C7 C6 1.381(6) . ?
C32 H32 0.9300 . ?
C32 C31 1.371(6) . ?
C39 H39 0.9300 . ?
C39 C38 1.382(5) . ?
C18 H18 0.9300 . ?
C18 C17 1.377(7) . ?
C16 H16 0.9300 . ?
C16 C17 1.393(6) . ?
C43 C42 1.377(6) . ?
C43 C54 1.495(6) . ?
C31 H31 0.9300 . ?
C31 C30 1.360(6) . ?
C41 H41 0.9300 . ?
C41 C42 1.384(5) . ?
C26 H26 0.9300 . ?
C26 C25 1.389(6) . ?
C10 H10 0.9300 . ?
C10 C11 1.377(5) . ?
C3 H3 0.9300 . ?
C3 C4 1.380(7) . ?
C37 H37 0.9300 . ?
C37 C38 1.369(6) . ?
C37 C36 1.362(6) . ?
C30 H30 0.9300 . ?
C38 H38 0.9300 . ?
C36 H36 0.9300 . ?
C36 C35 1.378(5) . ?
C12 H12 0.9300 . ?
C12 C11 1.349(7) . ?
C17 H17 0.9300 . ?
C35 H35 0.9300 . ?
C6 H6 0.9300 . ?
C6 C5 1.362(7) . ?
C24 H24 0.9300 . ?
C24 C25 1.364(8) . ?
C24 C23 1.346(8) . ?
C11 H11 0.9300 . ?
C42 H42 0.9300 . ?
C25 H25 0.9300 . ?
C54 H54A 0.9600 . ?
C54 H54B 0.9600 . ?
C54 H54C 0.9600 . ?
C23 H23 0.9300 . ?
C5 H5 0.9300 . ?
C5 C4 1.366(7) . ?
C4 H4 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
P8 Ni1 P27 110.90(4) . . ?
C47 Ni1 P8 142.90(10) . . ?
C47 Ni1 P27 104.80(10) . . ?
C48 Ni1 P8 103.49(10) . . ?
C48 Ni1 P27 145.55(10) . . ?
C48 Ni1 C47 42.15(14) . . ?
C9 P8 Ni1 113.59(11) . . ?
C15 P8 Ni1 114.48(12) . . ?
C15 P8 C9 99.88(16) . . ?
C15 P8 C2 102.78(17) . . ?
C2 P8 Ni1 120.94(12) . . ?
C2 P8 C9 102.40(16) . . ?
C28 P27 Ni1 114.91(13) . . ?
C34 P27 Ni1 117.72(11) . . ?
C34 P27 C28 97.85(16) . . ?
C34 P27 C21 102.06(16) . . ?
C21 P27 Ni1 115.55(12) . . ?
C21 P27 C28 106.49(17) . . ?
C28 C29 H29 119.5 . . ?
C28 C29 C30 121.0(4) . . ?
C30 C29 H29 119.5 . . ?
O53 C46 C47 121.1(3) . . ?
O53 C46 C40 118.4(3) . . ?
C47 C46 C40 120.5(3) . . ?
Ni1 C47 H47 119.1 . . ?
C46 C47 Ni1 100.9(2) . . ?
C46 C47 H47 119.1 . . ?
C48 C47 Ni1 67.78(18) . . ?
C48 C47 C46 117.6(3) . . ?
C48 C47 H47 119.1 . . ?
C45 C40 C46 123.3(3) . . ?
C45 C40 C41 118.6(3) . . ?
C41 C40 C46 118.0(3) . . ?
C9 C14 H14 119.8 . . ?
C13 C14 H14 119.8 . . ?
C13 C14 C9 120.4(4) . . ?
Ni1 C48 H48 114.5 . . ?
C47 C48 Ni1 70.07(19) . . ?
C47 C48 H48 114.5 . . ?
C47 C48 C49 117.7(3) . . ?
C49 C48 Ni1 118.5(3) . . ?
C49 C48 H48 114.5 . . ?
C14 C9 P8 119.4(3) . . ?
C10 C9 P8 122.3(3) . . ?
C10 C9 C14 118.3(3) . . ?
C14 C13 H13 119.6 . . ?
C12 C13 C14 120.9(4) . . ?
C12 C13 H13 119.6 . . ?
C29 C28 P27 119.7(3) . . ?
C29 C28 C33 118.4(4) . . ?
C33 C28 P27 121.6(3) . . ?
F50 C49 F52 104.8(3) . . ?
F50 C49 F51 106.1(3) . . ?
F50 C49 C48 114.2(3) . . ?
F52 C49 C48 113.7(3) . . ?
F51 C49 F52 104.1(3) . . ?
F51 C49 C48 113.0(3) . . ?
C28 C33 H33 119.9 . . ?
C32 C33 C28 120.3(4) . . ?
C32 C33 H33 119.9 . . ?
C40 C45 H45 119.6 . . ?
C44 C45 C40 120.9(4) . . ?
C44 C45 H45 119.6 . . ?
C20 C15 P8 117.6(3) . . ?
C16 C15 P8 123.9(3) . . ?
C16 C15 C20 118.1(4) . . ?
C45 C44 H44 119.4 . . ?
C45 C44 C43 121.1(4) . . ?
C43 C44 H44 119.4 . . ?
C39 C34 P27 123.3(3) . . ?
C39 C34 C35 119.1(3) . . ?
C35 C34 P27 117.5(3) . . ?
C7 C2 P8 118.4(3) . . ?
C3 C2 P8 123.5(3) . . ?
C3 C2 C7 118.2(4) . . ?
C20 C19 H19 119.9 . . ?
C18 C19 H19 119.9 . . ?
C18 C19 C20 120.3(5) . . ?
C21 C22 H22 120.0 . . ?
C21 C22 C23 120.0(4) . . ?
C23 C22 H22 120.0 . . ?
C15 C20 H20 119.3 . . ?
C19 C20 C15 121.4(4) . . ?
C19 C20 H20 119.3 . . ?
C22 C21 P27 117.0(3) . . ?
C26 C21 P27 124.4(3) . . ?
C26 C21 C22 118.6(4) . . ?
C2 C7 H7 119.6 . . ?
C2 C7 C6 120.7(4) . . ?
C6 C7 H7 119.6 . . ?
C33 C32 H32 119.9 . . ?
C31 C32 C33 120.1(4) . . ?
C31 C32 H32 119.9 . . ?
C34 C39 H39 119.8 . . ?
C34 C39 C38 120.5(4) . . ?
C38 C39 H39 119.8 . . ?
C19 C18 H18 120.4 . . ?
C19 C18 C17 119.2(4) . . ?
C17 C18 H18 120.4 . . ?
C15 C16 H16 120.1 . . ?
C15 C16 C17 119.9(5) . . ?
C17 C16 H16 120.1 . . ?
C44 C43 C54 121.6(4) . . ?
C42 C43 C44 117.7(4) . . ?
C42 C43 C54 120.7(4) . . ?
C32 C31 H31 119.9 . . ?
C30 C31 C32 120.3(4) . . ?
C30 C31 H31 119.9 . . ?
C40 C41 H41 120.0 . . ?
C42 C41 C40 120.0(4) . . ?
C42 C41 H41 120.0 . . ?
C21 C26 H26 119.7 . . ?
C21 C26 C25 120.5(5) . . ?
C25 C26 H26 119.7 . . ?
C9 C10 H10 120.1 . . ?
C11 C10 C9 119.8(4) . . ?
C11 C10 H10 120.1 . . ?
C2 C3 H3 119.5 . . ?
C2 C3 C4 121.1(4) . . ?
C4 C3 H3 119.5 . . ?
C38 C37 H37 119.9 . . ?
C36 C37 H37 119.9 . . ?
C36 C37 C38 120.2(4) . . ?
C29 C30 H30 120.1 . . ?
C31 C30 C29 119.8(4) . . ?
C31 C30 H30 120.1 . . ?
C39 C38 H38 120.1 . . ?
C37 C38 C39 119.8(4) . . ?
C37 C38 H38 120.1 . . ?
C37 C36 H36 119.5 . . ?
C37 C36 C35 121.0(4) . . ?
C35 C36 H36 119.5 . . ?
C13 C12 H12 120.6 . . ?
C11 C12 C13 118.7(4) . . ?
C11 C12 H12 120.6 . . ?
C18 C17 C16 121.2(4) . . ?
C18 C17 H17 119.4 . . ?
C16 C17 H17 119.4 . . ?
C34 C35 H35 120.3 . . ?
C36 C35 C34 119.5(4) . . ?
C36 C35 H35 120.3 . . ?
C7 C6 H6 120.0 . . ?
C5 C6 C7 120.0(4) . . ?
C5 C6 H6 120.0 . . ?
C25 C24 H24 120.0 . . ?
C23 C24 H24 120.0 . . ?
C23 C24 C25 120.0(5) . . ?
C10 C11 H11 119.1 . . ?
C12 C11 C10 121.9(4) . . ?
C12 C11 H11 119.1 . . ?
C43 C42 C41 121.7(4) . . ?
C43 C42 H42 119.2 . . ?
C41 C42 H42 119.2 . . ?
C26 C25 H25 120.0 . . ?
C24 C25 C26 120.1(5) . . ?
C24 C25 H25 120.0 . . ?
C43 C54 H54A 109.5 . . ?
C43 C54 H54B 109.5 . . ?
C43 C54 H54C 109.5 . . ?
H54A C54 H54B 109.5 . . ?
H54A C54 H54C 109.5 . . ?
H54B C54 H54C 109.5 . . ?
C22 C23 H23 119.6 . . ?
C24 C23 C22 120.8(5) . . ?
C24 C23 H23 119.6 . . ?
C6 C5 H5 119.9 . . ?
C6 C5 C4 120.2(5) . . ?
C4 C5 H5 119.9 . . ?
C3 C4 H4 120.1 . . ?
C5 C4 C3 119.8(5) . . ?
C5 C4 H4 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
Ni1 P8 C9 C14 -74.5(3) . . . . ?
Ni1 P8 C9 C10 103.1(3) . . . . ?
Ni1 P8 C15 C20 -37.7(3) . . . . ?
Ni1 P8 C15 C16 149.7(3) . . . . ?
Ni1 P8 C2 C7 -31.2(4) . . . . ?
Ni1 P8 C2 C3 149.3(3) . . . . ?
Ni1 P27 C28 C29 -12.7(3) . . . . ?
Ni1 P27 C28 C33 161.5(3) . . . . ?
Ni1 P27 C34 C39 121.2(3) . . . . ?
Ni1 P27 C34 C35 -63.3(3) . . . . ?
Ni1 P27 C21 C22 -26.6(3) . . . . ?
Ni1 P27 C21 C26 153.0(3) . . . . ?
Ni1 C47 C48 C49 -112.6(3) . . . . ?
Ni1 C48 C49 F50 -36.0(4) . . . . ?
Ni1 C48 C49 F52 -156.2(3) . . . . ?
Ni1 C48 C49 F51 85.4(4) . . . . ?
P8 C9 C10 C11 -176.3(3) . . . . ?
P8 C15 C20 C19 -170.5(3) . . . . ?
P8 C15 C16 C17 170.9(3) . . . . ?
P8 C2 C7 C6 -178.8(4) . . . . ?
P8 C2 C3 C4 179.1(4) . . . . ?
P27 C28 C33 C32 -177.2(3) . . . . ?
P27 C34 C39 C38 174.7(3) . . . . ?
P27 C34 C35 C36 -173.5(3) . . . . ?
P27 C21 C26 C25 179.9(4) . . . . ?
O53 C46 C47 Ni1 -61.9(4) . . . . ?
O53 C46 C47 C48 8.6(5) . . . . ?
O53 C46 C40 C45 -158.3(4) . . . . ?
O53 C46 C40 C41 18.4(5) . . . . ?
C29 C28 C33 C32 -2.9(6) . . . . ?
C46 C47 C48 Ni1 -91.0(3) . . . . ?
C46 C47 C48 C49 156.4(3) . . . . ?
C46 C40 C45 C44 178.7(4) . . . . ?
C46 C40 C41 C42 -179.5(4) . . . . ?
C47 C46 C40 C45 21.6(5) . . . . ?
C47 C46 C40 C41 -161.6(3) . . . . ?
C47 C48 C49 F50 45.2(5) . . . . ?
C47 C48 C49 F52 -75.0(5) . . . . ?
C47 C48 C49 F51 166.6(3) . . . . ?
C40 C46 C47 Ni1 118.1(3) . . . . ?
C40 C46 C47 C48 -171.3(3) . . . . ?
C40 C45 C44 C43 -0.2(6) . . . . ?
C40 C41 C42 C43 1.5(7) . . . . ?
C14 C9 C10 C11 1.3(6) . . . . ?
C14 C13 C12 C11 1.9(7) . . . . ?
C9 P8 C15 C20 84.0(3) . . . . ?
C9 P8 C15 C16 -88.6(3) . . . . ?
C9 P8 C2 C7 -158.7(3) . . . . ?
C9 P8 C2 C3 21.7(4) . . . . ?
C9 C14 C13 C12 -1.3(6) . . . . ?
C9 C10 C11 C12 -0.8(7) . . . . ?
C13 C14 C9 P8 177.4(3) . . . . ?
C13 C14 C9 C10 -0.3(6) . . . . ?
C13 C12 C11 C10 -0.8(7) . . . . ?
C28 P27 C34 C39 -115.2(3) . . . . ?
C28 P27 C34 C35 60.2(3) . . . . ?
C28 P27 C21 C22 -155.5(3) . . . . ?
C28 P27 C21 C26 24.1(4) . . . . ?
C28 C29 C30 C31 0.3(6) . . . . ?
C28 C33 C32 C31 1.9(7) . . . . ?
C33 C32 C31 C30 0.3(7) . . . . ?
C45 C40 C41 C42 -2.6(6) . . . . ?
C45 C44 C43 C42 -0.9(6) . . . . ?
C45 C44 C43 C54 178.2(4) . . . . ?
C15 P8 C9 C14 163.2(3) . . . . ?
C15 P8 C9 C10 -19.2(4) . . . . ?
C15 P8 C2 C7 98.0(4) . . . . ?
C15 P8 C2 C3 -81.6(4) . . . . ?
C15 C16 C17 C18 -0.3(7) . . . . ?
C44 C43 C42 C41 0.2(7) . . . . ?
C34 P27 C28 C29 -138.3(3) . . . . ?
C34 P27 C28 C33 35.9(3) . . . . ?
C34 P27 C21 C22 102.4(3) . . . . ?
C34 P27 C21 C26 -78.0(4) . . . . ?
C34 C39 C38 C37 -1.4(7) . . . . ?
C2 P8 C9 C14 57.6(3) . . . . ?
C2 P8 C9 C10 -124.8(3) . . . . ?
C2 P8 C15 C20 -170.7(3) . . . . ?
C2 P8 C15 C16 16.6(3) . . . . ?
C2 C7 C6 C5 0.0(8) . . . . ?
C2 C3 C4 C5 -0.6(10) . . . . ?
C19 C18 C17 C16 1.6(7) . . . . ?
C22 C21 C26 C25 -0.5(7) . . . . ?
C20 C15 C16 C17 -1.7(6) . . . . ?
C20 C19 C18 C17 -0.8(7) . . . . ?
C21 P27 C28 C29 116.6(3) . . . . ?
C21 P27 C28 C33 -69.2(3) . . . . ?
C21 P27 C34 C39 -6.4(3) . . . . ?
C21 P27 C34 C35 169.0(3) . . . . ?
C21 C22 C23 C24 -0.5(8) . . . . ?
C21 C26 C25 C24 -1.0(8) . . . . ?
C7 C2 C3 C4 -0.5(7) . . . . ?
C7 C6 C5 C4 -1.1(10) . . . . ?
C32 C31 C30 C29 -1.4(6) . . . . ?
C39 C34 C35 C36 2.2(6) . . . . ?
C18 C19 C20 C15 -1.3(6) . . . . ?
C16 C15 C20 C19 2.6(5) . . . . ?
C41 C40 C45 C44 2.0(6) . . . . ?
C3 C2 C7 C6 0.8(7) . . . . ?
C37 C36 C35 C34 -1.4(6) . . . . ?
C30 C29 C28 P27 176.2(3) . . . . ?
C30 C29 C28 C33 1.8(5) . . . . ?
C38 C37 C36 C35 -0.8(7) . . . . ?
C36 C37 C38 C39 2.2(7) . . . . ?
C35 C34 C39 C38 -0.7(6) . . . . ?
C6 C5 C4 C3 1.4(10) . . . . ?
C25 C24 C23 C22 -1.1(9) . . . . ?
C54 C43 C42 C41 -178.9(4) . . . . ?
C23 C22 C21 P27 -179.1(3) . . . . ?
C23 C22 C21 C26 1.3(6) . . . . ?
C23 C24 C25 C26 1.8(9) . . . . ?

_olex2_date_sample_data_collection 2019-10-31
_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 1.339
_oxdiff_exptl_absorpt_empirical_full_min 0.753
####################################################################### 
# 
# 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_bdc-1-20200921
_database_code_depnum_ccdc_archive 'CCDC 2034194'
loop_
_audit_author_name
_audit_author_address
CF-C
;htu
China
;
_audit_update_record             
;
2020-09-28 deposited with the CCDC.	2021-04-08 downloaded from the CCDC.
;
_audit_creation_date             2020-09-28
_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         'C26 H16 F6 O2'
_chemical_formula_sum            'C26 H16 F6 O2'
_chemical_formula_weight         474.39
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C1 H1 O1 N1 F1'
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      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                   10.26200(10)
_cell_length_b                   10.3101(2)
_cell_length_c                   22.0678(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2334.82(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    18380
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      71.3330
_cell_measurement_theta_min      4.2870
_shelx_estimated_absorpt_T_max   0.951
_shelx_estimated_absorpt_T_min   0.879
_exptl_absorpt_coefficient_mu    1.018
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.82190
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.350
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             968
_exptl_crystal_size_max          0.13
_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  0.0665
_diffrn_reflns_av_unetI/netI     0.0297
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            32602
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.496
_diffrn_reflns_theta_min         4.006
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0521
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     12.00 102.00   1.00    1.00    --   35.37  71.00  78.00   90
  2  ω    -32.00  59.00   1.00    1.00    --   35.37 -71.00 -52.00   91
  3  ω     41.00 128.00   1.00    1.37    --  107.12 -67.00 176.00   87
  4  ω     84.00 174.00   1.00    1.37    --  107.12  71.00  78.00   90
  5  ω     98.00 176.00   1.00    1.37    --  107.12  85.00-173.00   78
  6  ω    -57.00  31.00   1.00    1.00    --  -35.37  67.00 -49.00   88
  7  ω    -15.00  67.00   1.00    1.00    --   35.37 -85.00  67.00   82
  8  ω     57.00 108.00   1.00    1.00    --   35.37 178.00-120.00   51
  9  ω     16.00 105.00   1.00    1.00    --   35.37  38.00  60.00   89
 10  ω     57.00 108.00   1.00    1.00    --   35.37 178.00 120.00   51
 11  ω     19.00 103.00   1.00    1.00    --   35.37  57.00  60.00   84
 12  ω     86.00 177.00   1.00    1.37    --  107.12  30.00  90.00   91
 13  ω     37.00 113.00   1.00    1.37    --  107.12-111.00 150.00   76
 14  ω     86.00 177.00   1.00    1.37    --  107.12  30.00 150.00   91
 15  ω     89.00 174.00   1.00    1.37    --  107.12  61.00  60.00   85
 16  ω     90.00 176.00   1.00    1.37    --  107.12  45.00  60.00   86
 17  ω     38.00 110.00   1.00    1.37    --  107.12 -95.00 -90.00   72
 18  ω     69.00 178.00   1.00    1.37    --  107.12  15.00  90.00  109
 19  ω     37.00 113.00   1.00    1.37    --  107.12-111.00-180.00   76
 20  ω     90.00 176.00   1.00    1.37    --  107.12  45.00  90.00   86
 21  ω     19.00 103.00   1.00    1.00    --   35.37  57.00-120.00   84
 22  ω     -1.00  25.00   1.00    1.00    --   35.37  95.00-179.14   26
 23  ω     57.00 108.00   1.00    1.00    --   35.37 178.00 -60.00   51
 24  ω     16.00 105.00   1.00    1.00    --   35.37  38.00-150.00   89
 25  ω    -34.00  54.00   1.00    1.00    --   35.37 -38.00 120.00   88
 26  ω     19.00 103.00   1.00    1.00    --   35.37  57.00 -30.00   84
 27  ω      9.00 103.00   1.00    1.00    --   35.37  77.00 -90.00   94
 28  ω     38.00 110.00   1.00    1.37    --  107.12 -95.00  30.00   72
 29  ω     80.00 175.00   1.00    1.37    --  107.12  77.00 -60.00   95
 30  ω     80.00 175.00   1.00    1.37    --  107.12  77.00-180.00   95
 31  ω     40.00 125.00   1.00    1.37    --  107.12 -61.00 -60.00   85
 32  ω     89.00 174.00   1.00    1.37    --  107.12  61.00   0.00   85
 33  ω     89.00 174.00   1.00    1.37    --  107.12  61.00-120.00   85
 34  ω     80.00 175.00   1.00    1.37    --  107.12  77.00-150.00   95
 35  ω     80.00 175.00   1.00    1.37    --  107.12  77.00 -30.00   95
 36  ω     80.00 175.00   1.00    1.37    --  107.12  77.00 150.00   95
 37  ω     80.00 175.00   1.00    1.37    --  107.12  77.00 -90.00   95
 38  ω     69.00 178.00   1.00    1.37    --  107.12  15.00 -30.00  109
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0795863000
_diffrn_orient_matrix_UB_12      0.1171047000
_diffrn_orient_matrix_UB_13      -0.0226487000
_diffrn_orient_matrix_UB_21      0.1055806000
_diffrn_orient_matrix_UB_22      0.0288233000
_diffrn_orient_matrix_UB_23      -0.0477674000
_diffrn_orient_matrix_UB_31      -0.0711125000
_diffrn_orient_matrix_UB_32      -0.0882155000
_diffrn_orient_matrix_UB_33      -0.0455929000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.747
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.987
_reflns_number_gt                4128
_reflns_number_total             4522
_reflns_odcompleteness_completeness 99.96
_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.
 
 Structure factors included contributions from the .fab file.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 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 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.273
_refine_diff_density_min         -0.461
_refine_diff_density_rms         0.114
_refine_ls_abs_structure_details 
;
 Flack x determined using 1567 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.01(6)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.251
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     335
_refine_ls_number_reflns         4522
_refine_ls_number_restraints     42
_refine_ls_R_factor_all          0.0760
_refine_ls_R_factor_gt           0.0720
_refine_ls_restrained_S_all      1.330
_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)+(0.0970P)²+0.4230P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1840
_refine_ls_wR_factor_ref         0.1867
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Restrained distances
 C1-F5 = C1-F5A = C1-F6 = C1-F6A = C1-F7 = C1-F7A
 1.27 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
Uanis(F5) \\sim Ueq, Uanis(F6) \\sim Ueq, Uanis(F7) \\sim Ueq: with sigma of
0.01 and sigma for terminal atoms of 0.02
Uanis(F7) \\sim Ueq, Uanis(F5A) \\sim Ueq, Uanis(F5) \\sim Ueq, Uanis(F6A)
\\sim Ueq, Uanis(F6) \\sim Ueq, Uanis(F7A) \\sim Ueq: with sigma of 0.005 and
sigma for terminal atoms of 0.01
4. Others
 Sof(F5A)=Sof(F7A)=Sof(F6A)=1-FVAR(1)
 Sof(F5)=Sof(F7)=Sof(F6)=FVAR(1)
5.a Aromatic/amide H refined with riding coordinates:
 C00B(H00B), C00C(H00C), C00D(H00D), C00E(H00E), C00F(H00F), C00G(H00G),
 C00H(H00H), C00K(H00K), C00L(H00L), C00N(H00N), C00O(H00O), C00S(H00S),
 C00T(H00T), C00U(H00U), C00X(H00X), C00Y(H00Y)
;
_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
F001 F 0.6558(3) 0.4510(4) 0.11755(15) 0.0848(9) Uani 1 1 d . . . . .
O002 O 0.4472(3) 0.4223(3) 0.24444(14) 0.0604(8) Uani 1 1 d . . . . .
F003 F 0.4856(3) 0.3322(3) 0.13046(17) 0.0908(10) Uani 1 1 d . . . . .
F004 F 0.6528(4) 0.3058(4) 0.18722(19) 0.1012(12) Uani 1 1 d . . . . .
O005 O 0.2369(3) 0.4099(4) 0.26937(18) 0.0830(12) Uani 1 1 d . . . . .
C006 C 0.4301(3) 0.5856(4) 0.17153(16) 0.0446(8) Uani 1 1 d . . . . .
C007 C 0.3107(3) 0.5606(4) 0.19213(17) 0.0462(8) Uani 1 1 d . . . . .
C008 C 0.4666(3) 0.6737(4) 0.12174(15) 0.0460(8) Uani 1 1 d . . . . .
C009 C 0.1836(3) 0.6163(4) 0.17528(16) 0.0442(8) Uani 1 1 d . . . . .
C00A C 0.7580(4) 0.6012(4) 0.33438(17) 0.0485(8) Uani 1 1 d . . . . .
C00B C 0.6459(4) 0.5565(4) 0.29743(18) 0.0525(9) Uani 1 1 d . . . . .
H00B H 0.573836 0.525418 0.318476 0.063 Uiso 1 1 calc R U . . .
C00C C 0.6379(3) 0.5565(4) 0.23812(18) 0.0495(9) Uani 1 1 d . . . . .
H00C H 0.704070 0.596100 0.216074 0.059 Uiso 1 1 calc R U . . .
C00D C 0.5653(4) 0.7648(4) 0.12706(18) 0.0507(9) Uani 1 1 d . . . . .
H00D H 0.612146 0.770370 0.163046 0.061 Uiso 1 1 calc R U . . .
C00E C 0.9781(5) 0.6769(5) 0.34621(19) 0.0612(11) Uani 1 1 d . . . . .
H00E H 1.055524 0.705675 0.328888 0.073 Uiso 1 1 calc R U . . .
C00F C 0.8727(4) 0.6472(5) 0.31004(17) 0.0571(10) Uani 1 1 d . . . . .
H00F H 0.879163 0.658451 0.268336 0.069 Uiso 1 1 calc R U . . .
C00G C -0.0573(4) 0.7147(6) 0.1433(2) 0.0678(13) Uani 1 1 d . . . . .
H00G H -0.138057 0.748003 0.132109 0.081 Uiso 1 1 calc R U . . .
C00H C 0.0849(4) 0.5352(5) 0.1559(2) 0.0614(11) Uani 1 1 d . . . . .
H00H H 0.098323 0.446090 0.154094 0.074 Uiso 1 1 calc R U . . .
C00I C 0.3197(4) 0.4587(5) 0.2386(2) 0.0573(10) Uani 1 1 d . . . . .
C00J C 0.5260(4) 0.4948(4) 0.20382(18) 0.0514(9) Uani 1 1 d . . . . .
C00K C 0.1596(5) 0.7466(5) 0.1792(2) 0.0659(12) Uani 1 1 d . . . . .
H00K H 0.224967 0.802681 0.192146 0.079 Uiso 1 1 calc R U . . .
C00L C 0.0374(5) 0.7954(6) 0.1640(3) 0.0776(14) Uani 1 1 d . . . . .
H00L H 0.020532 0.883595 0.167979 0.093 Uiso 1 1 calc R U . . .
C00M C 0.9682(5) 0.6635(5) 0.40835(19) 0.0606(11) Uani 1 1 d . . . . .
C00N C -0.0343(4) 0.5873(6) 0.1391(2) 0.0725(14) Uani 1 1 d . . . . .
H00N H -0.099415 0.532700 0.124687 0.087 Uiso 1 1 calc R U . . .
C00O C 0.7499(5) 0.5897(7) 0.3966(2) 0.0796(17) Uani 1 1 d . . . . .
H00O H 0.672798 0.560736 0.414059 0.095 Uiso 1 1 calc R U . . .
C00P C 0.5804(5) 0.3952(5) 0.1592(2) 0.0670(12) Uani 1 1 d . . . . .
F5 F 1.0790(11) 0.6473(14) 0.5010(3) 0.119(4) Uani 0.589(16) 1 d D U P A 1
C1 C 1.0838(6) 0.6938(6) 0.4478(2) 0.0862(18) Uani 1 1 d D . . . .
C00S C 0.5951(5) 0.8469(6) 0.0800(2) 0.0713(13) Uani 1 1 d . . . . .
H00S H 0.661539 0.907560 0.084382 0.086 Uiso 1 1 calc R U . . .
C00T C 0.8542(6) 0.6205(7) 0.4333(2) 0.0853(18) Uani 1 1 d . . . . .
H00T H 0.846998 0.611915 0.475118 0.102 Uiso 1 1 calc R U . . .
C00U C 0.3960(6) 0.6688(7) 0.0679(2) 0.0852(19) Uani 1 1 d . . . . .
H00U H 0.327655 0.610295 0.063589 0.102 Uiso 1 1 calc R U . . .
F7 F 1.1038(14) 0.8186(8) 0.4528(7) 0.134(5) Uani 0.589(16) 1 d D U P A 1
F6 F 1.1977(8) 0.6593(17) 0.4230(5) 0.139(5) Uani 0.589(16) 1 d D U P A 1
C00X C 0.5271(7) 0.8395(9) 0.0269(3) 0.102(2) Uani 1 1 d . . . . .
H00X H 0.548070 0.894287 -0.005148 0.123 Uiso 1 1 calc R U . . .
C00Y C 0.4281(8) 0.7512(10) 0.0208(3) 0.122(3) Uani 1 1 d . . . . .
H00Y H 0.381925 0.746801 -0.015440 0.147 Uiso 1 1 calc R U . . .
F5A F 1.0442(15) 0.758(2) 0.4967(7) 0.147(7) Uani 0.411(16) 1 d D U P A 2
F7A F 1.1663(15) 0.766(2) 0.4254(6) 0.115(5) Uani 0.411(16) 1 d D U P A 2
F6A F 1.1367(15) 0.5875(12) 0.4688(10) 0.133(6) Uani 0.411(16) 1 d D U P A 2


_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 C00P 1.332(6) . ?
O002 C00I 1.367(5) . ?
O002 C00J 1.420(5) . ?
F003 C00P 1.330(5) . ?
F004 C00P 1.336(6) . ?
O005 C00I 1.199(5) . ?
C006 C007 1.333(5) . ?
C006 C008 1.474(5) . ?
C006 C00J 1.533(5) . ?
C007 C009 1.473(5) . ?
C007 C00I 1.471(6) . ?
C008 C00D 1.386(5) . ?
C008 C00U 1.393(5) . ?
C009 C00H 1.381(5) . ?
C009 C00K 1.369(6) . ?
C00A C00B 1.484(5) . ?
C00A C00F 1.378(6) . ?
C00A C00O 1.380(6) . ?
C00B H00B 0.9300 . ?
C00B C00C 1.311(6) . ?
C00C H00C 0.9300 . ?
C00C C00J 1.515(5) . ?
C00D H00D 0.9300 . ?
C00D C00S 1.373(6) . ?
C00E H00E 0.9300 . ?
C00E C00F 1.379(6) . ?
C00E C00M 1.382(6) . ?
C00F H00F 0.9300 . ?
C00G H00G 0.9300 . ?
C00G C00L 1.358(8) . ?
C00G C00N 1.338(8) . ?
C00H H00H 0.9300 . ?
C00H C00N 1.386(7) . ?
C00J C00P 1.528(7) . ?
C00K H00K 0.9300 . ?
C00K C00L 1.392(7) . ?
C00L H00L 0.9300 . ?
C00M C1 1.505(6) . ?
C00M C00T 1.367(7) . ?
C00N H00N 0.9300 . ?
C00O H00O 0.9300 . ?
C00O C00T 1.379(7) . ?
F5 C1 1.268(7) . ?
C1 F7 1.308(9) . ?
C1 F6 1.339(9) . ?
C1 F5A 1.327(11) . ?
C1 F7A 1.229(9) . ?
C1 F6A 1.308(10) . ?
C00S H00S 0.9300 . ?
C00S C00X 1.367(8) . ?
C00T H00T 0.9300 . ?
C00U H00U 0.9300 . ?
C00U C00Y 1.382(8) . ?
C00X H00X 0.9300 . ?
C00X C00Y 1.371(10) . ?
C00Y H00Y 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
C00I O002 C00J 109.9(3) . . ?
C007 C006 C008 127.4(3) . . ?
C007 C006 C00J 108.2(3) . . ?
C008 C006 C00J 124.1(3) . . ?
C006 C007 C009 130.8(3) . . ?
C006 C007 C00I 108.5(3) . . ?
C00I C007 C009 120.7(3) . . ?
C00D C008 C006 122.7(3) . . ?
C00D C008 C00U 118.5(4) . . ?
C00U C008 C006 118.8(4) . . ?
C00H C009 C007 119.4(4) . . ?
C00K C009 C007 121.7(4) . . ?
C00K C009 C00H 118.8(4) . . ?
C00F C00A C00B 123.7(3) . . ?
C00F C00A C00O 117.9(4) . . ?
C00O C00A C00B 118.3(4) . . ?
C00A C00B H00B 116.7 . . ?
C00C C00B C00A 126.7(4) . . ?
C00C C00B H00B 116.7 . . ?
C00B C00C H00C 118.5 . . ?
C00B C00C C00J 123.1(4) . . ?
C00J C00C H00C 118.5 . . ?
C008 C00D H00D 119.5 . . ?
C00S C00D C008 121.1(4) . . ?
C00S C00D H00D 119.5 . . ?
C00F C00E H00E 120.2 . . ?
C00F C00E C00M 119.6(4) . . ?
C00M C00E H00E 120.2 . . ?
C00A C00F C00E 121.4(4) . . ?
C00A C00F H00F 119.3 . . ?
C00E C00F H00F 119.3 . . ?
C00L C00G H00G 120.1 . . ?
C00N C00G H00G 120.1 . . ?
C00N C00G C00L 119.9(4) . . ?
C009 C00H H00H 120.2 . . ?
C009 C00H C00N 119.7(5) . . ?
C00N C00H H00H 120.2 . . ?
O002 C00I C007 108.8(3) . . ?
O005 C00I O002 120.7(4) . . ?
O005 C00I C007 130.5(4) . . ?
O002 C00J C006 104.5(3) . . ?
O002 C00J C00C 109.7(3) . . ?
O002 C00J C00P 105.1(4) . . ?
C00C C00J C006 117.5(3) . . ?
C00C C00J C00P 109.1(3) . . ?
C00P C00J C006 110.2(3) . . ?
C009 C00K H00K 120.0 . . ?
C009 C00K C00L 120.1(4) . . ?
C00L C00K H00K 120.0 . . ?
C00G C00L C00K 120.3(5) . . ?
C00G C00L H00L 119.8 . . ?
C00K C00L H00L 119.8 . . ?
C00E C00M C1 119.7(4) . . ?
C00T C00M C00E 119.7(4) . . ?
C00T C00M C1 120.6(4) . . ?
C00G C00N C00H 121.2(5) . . ?
C00G C00N H00N 119.4 . . ?
C00H C00N H00N 119.4 . . ?
C00A C00O H00O 119.4 . . ?
C00T C00O C00A 121.2(5) . . ?
C00T C00O H00O 119.4 . . ?
F001 C00P F004 107.1(4) . . ?
F001 C00P C00J 111.5(4) . . ?
F003 C00P F001 107.8(4) . . ?
F003 C00P F004 106.9(4) . . ?
F003 C00P C00J 111.6(4) . . ?
F004 C00P C00J 111.7(4) . . ?
F5 C1 C00M 115.2(6) . . ?
F5 C1 F7 107.5(9) . . ?
F5 C1 F6 108.2(9) . . ?
F7 C1 C00M 112.1(6) . . ?
F7 C1 F6 99.1(10) . . ?
F6 C1 C00M 113.3(6) . . ?
F5A C1 C00M 109.4(7) . . ?
F7A C1 C00M 115.7(7) . . ?
F7A C1 F5A 103.8(13) . . ?
F7A C1 F6A 111.2(12) . . ?
F6A C1 C00M 111.0(7) . . ?
F6A C1 F5A 104.9(13) . . ?
C00D C00S H00S 120.0 . . ?
C00X C00S C00D 120.0(5) . . ?
C00X C00S H00S 120.0 . . ?
C00M C00T C00O 120.1(4) . . ?
C00M C00T H00T 119.9 . . ?
C00O C00T H00T 119.9 . . ?
C008 C00U H00U 120.1 . . ?
C00Y C00U C008 119.7(5) . . ?
C00Y C00U H00U 120.1 . . ?
C00S C00X H00X 120.0 . . ?
C00S C00X C00Y 120.0(5) . . ?
C00Y C00X H00X 120.0 . . ?
C00U C00Y H00Y 119.6 . . ?
C00X C00Y C00U 120.7(5) . . ?
C00X C00Y H00Y 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
O002 C00J C00P F001 179.2(3) . . . . ?
O002 C00J C00P F003 58.6(5) . . . . ?
O002 C00J C00P F004 -61.0(5) . . . . ?
C006 C007 C009 C00H 123.6(5) . . . . ?
C006 C007 C009 C00K -57.5(7) . . . . ?
C006 C007 C00I O002 -0.9(5) . . . . ?
C006 C007 C00I O005 178.1(5) . . . . ?
C006 C008 C00D C00S -178.8(4) . . . . ?
C006 C008 C00U C00Y 179.5(7) . . . . ?
C006 C00J C00P F001 67.2(4) . . . . ?
C006 C00J C00P F003 -53.5(5) . . . . ?
C006 C00J C00P F004 -173.0(4) . . . . ?
C007 C006 C008 C00D 131.9(4) . . . . ?
C007 C006 C008 C00U -45.6(7) . . . . ?
C007 C006 C00J O002 -1.6(4) . . . . ?
C007 C006 C00J C00C -123.4(4) . . . . ?
C007 C006 C00J C00P 110.9(4) . . . . ?
C007 C009 C00H C00N -179.0(4) . . . . ?
C007 C009 C00K C00L -178.8(5) . . . . ?
C008 C006 C007 C009 -4.3(7) . . . . ?
C008 C006 C007 C00I 175.2(4) . . . . ?
C008 C006 C00J O002 -175.5(3) . . . . ?
C008 C006 C00J C00C 62.7(5) . . . . ?
C008 C006 C00J C00P -63.0(5) . . . . ?
C008 C00D C00S C00X -0.1(8) . . . . ?
C008 C00U C00Y C00X -1.2(14) . . . . ?
C009 C007 C00I O002 178.6(4) . . . . ?
C009 C007 C00I O005 -2.4(8) . . . . ?
C009 C00H C00N C00G -2.3(8) . . . . ?
C009 C00K C00L C00G -2.1(9) . . . . ?
C00A C00B C00C C00J 172.7(4) . . . . ?
C00A C00O C00T C00M 0.2(11) . . . . ?
C00B C00A C00F C00E -174.3(4) . . . . ?
C00B C00A C00O C00T 175.2(6) . . . . ?
C00B C00C C00J O002 -9.3(6) . . . . ?
C00B C00C C00J C006 109.7(5) . . . . ?
C00B C00C C00J C00P -124.0(5) . . . . ?
C00C C00J C00P F001 -63.2(4) . . . . ?
C00C C00J C00P F003 176.1(4) . . . . ?
C00C C00J C00P F004 56.6(5) . . . . ?
C00D C008 C00U C00Y 1.9(10) . . . . ?
C00D C00S C00X C00Y 0.9(12) . . . . ?
C00E C00M C1 F5 -161.9(10) . . . . ?
C00E C00M C1 F7 74.7(11) . . . . ?
C00E C00M C1 F6 -36.5(11) . . . . ?
C00E C00M C1 F5A 138.5(14) . . . . ?
C00E C00M C1 F7A 21.8(16) . . . . ?
C00E C00M C1 F6A -106.2(13) . . . . ?
C00E C00M C00T C00O 0.4(10) . . . . ?
C00F C00A C00B C00C -1.5(7) . . . . ?
C00F C00A C00O C00T -1.4(9) . . . . ?
C00F C00E C00M C1 179.0(5) . . . . ?
C00F C00E C00M C00T 0.3(8) . . . . ?
C00H C009 C00K C00L 0.1(7) . . . . ?
C00I O002 C00J C006 1.0(4) . . . . ?
C00I O002 C00J C00C 127.8(4) . . . . ?
C00I O002 C00J C00P -115.1(4) . . . . ?
C00I C007 C009 C00H -55.8(6) . . . . ?
C00I C007 C009 C00K 123.1(5) . . . . ?
C00J O002 C00I O005 -179.2(5) . . . . ?
C00J O002 C00I C007 -0.1(5) . . . . ?
C00J C006 C007 C009 -177.9(4) . . . . ?
C00J C006 C007 C00I 1.5(5) . . . . ?
C00J C006 C008 C00D -55.3(6) . . . . ?
C00J C006 C008 C00U 127.1(5) . . . . ?
C00K C009 C00H C00N 2.0(7) . . . . ?
C00L C00G C00N C00H 0.4(8) . . . . ?
C00M C00E C00F C00A -1.7(8) . . . . ?
C00N C00G C00L C00K 1.8(9) . . . . ?
C00O C00A C00B C00C -177.9(5) . . . . ?
C00O C00A C00F C00E 2.2(8) . . . . ?
C1 C00M C00T C00O -178.3(6) . . . . ?
C00S C00X C00Y C00U -0.2(14) . . . . ?
C00T C00M C1 F5 16.7(12) . . . . ?
C00T C00M C1 F7 -106.7(11) . . . . ?
C00T C00M C1 F6 142.1(10) . . . . ?
C00T C00M C1 F5A -42.8(15) . . . . ?
C00T C00M C1 F7A -159.6(15) . . . . ?
C00T C00M C1 F6A 72.5(14) . . . . ?
C00U C008 C00D C00S -1.2(7) . . . . ?

_smtbx_masks_special_details     ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 0.204 0.907 0.983 7.1 1.4 ?
2 0.296 0.093 0.483 7.1 1.4 ?
3 0.704 0.593 0.017 7.1 1.4 ?
4 0.796 0.407 0.517 7.1 1.4 ?

_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_olex2_date_sample_data_collection 2020-09-21
_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 2.876
_oxdiff_exptl_absorpt_empirical_full_min 0.638
####################################################################### 
# 
# 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_bdc-2-20200921
_database_code_depnum_ccdc_archive 'CCDC 2034195'
loop_
_audit_author_name
_audit_author_address
CF-I
;htu
China
;
_audit_update_record             
;
2020-09-28 deposited with the CCDC.	2021-04-08 downloaded from the CCDC.
;
_audit_creation_date             2020-09-28
_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 H15 F9 O2'
_chemical_formula_sum            'C27 H15 F9 O2'
_chemical_formula_weight         542.39
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C1 H1 O1 N1 F1'
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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   8.30301(10)
_cell_length_b                   11.22179(15)
_cell_length_c                   26.6950(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2487.30(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    15567
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.0600
_cell_measurement_theta_min      3.9210
_shelx_estimated_absorpt_T_max   0.942
_shelx_estimated_absorpt_T_min   0.849
_exptl_absorpt_coefficient_mu    1.210
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.32041
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.448
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             1096
_exptl_crystal_size_max          0.14
_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  0.0427
_diffrn_reflns_av_unetI/netI     0.0193
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            36696
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.470
_diffrn_reflns_theta_min         4.274
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0521
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -103.00  -9.00   1.00    1.00    --  -35.62 -77.00   7.00   94
  2  ω     -6.00  71.00   1.00    1.00    --   35.62 -93.00 -90.00   77
  3  ω     38.00 109.00   1.00    1.30    --  107.12 -93.00 -90.00   71
  4  ω     91.00 175.00   1.00    1.30    --  107.12  56.00 -80.00   84
  5  ω     40.00 134.00   1.00    1.30    --  107.12 -77.00   7.00   94
  6  ω   -108.00 -35.00   1.00    1.00    --  -35.62-178.00 -90.00   73
  7  ω   -105.00 -17.00   1.00    1.00    --  -35.62 -38.00 -90.00   88
  8  ω     57.00 108.00   1.00    1.00    --   35.62 178.00  60.00   51
  9  ω    -32.00  52.00   1.00    1.00    --   35.62 -56.00 136.00   84
 10  ω     90.00 176.00   1.00    1.30    --  107.12  45.00-150.00   86
 11  ω     37.00 113.00   1.00    1.30    --  107.12-111.00  90.00   76
 12  ω     90.00 176.00   1.00    1.30    --  107.12  45.00 -90.00   86
 13  ω     38.00 110.00   1.00    1.30    --  107.12 -95.00 -30.00   72
 14  ω     40.00 134.00   1.00    1.30    --  107.12 -77.00 120.00   94
 15  ω    100.00 177.00   1.00    1.30    --  107.12 111.00 -30.00   77
 16  ω   -105.00 -17.00   1.00    1.00    --  -35.62 -38.00  30.00   88
 17  ω   -103.00  -9.00   1.00    1.00    --  -35.62 -77.00 -90.00   94
 18  ω     19.00 103.00   1.00    1.00    --   35.62  57.00-120.00   84
 19  ω     57.00 108.00   1.00    1.00    --   35.62 178.00-180.00   51
 20  ω      9.00 103.00   1.00    1.00    --   35.62  77.00 133.00   94
 21  ω     69.00 178.00   1.00    1.30    --  107.12  15.00  30.00  109
 22  ω     80.00 175.00   1.00    1.30    --  107.12  77.00 120.00   95
 23  ω     69.00 178.00   1.00    1.30    --  107.12  15.00 120.00  109
 24  ω     90.00 176.00   1.00    1.30    --  107.12  45.00-120.00   86
 25  ω     80.00 175.00   1.00    1.30    --  107.12  77.00 -60.00   95
 26  ω     39.00 125.00   1.00    1.30    --  107.12 -45.00-150.00   86
 27  ω     80.00 175.00   1.00    1.30    --  107.12  77.00  30.00   95
 28  ω     90.00 176.00   1.00    1.30    --  107.12  45.00-180.00   86
 29  ω     80.00 175.00   1.00    1.30    --  107.12  77.00   0.00   95
 30  ω     89.00 174.00   1.00    1.30    --  107.12  61.00 150.00   85
 31  ω    -52.00  32.00   1.00    1.00    --  -35.62  57.00 -90.00   84
 32  ω   -105.00 -17.00   1.00    1.00    --  -35.62 -38.00 120.00   88
 33  ω      9.00 103.00   1.00    1.00    --   35.62  77.00  30.00   94
 34  ω      9.00 103.00   1.00    1.00    --   35.62  77.00-150.00   94
 35  ω      1.00  75.00   1.00    1.00    --   35.62 -99.00  90.00   74
 36  ω     80.00 175.00   1.00    1.30    --  107.12  77.00  60.00   95
 37  ω     80.00 175.00   1.00    1.30    --  107.12  77.00  90.00   95
 38  ω     80.00 105.00   1.00    1.30    --  107.12  77.00 -30.00   25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1408543000
_diffrn_orient_matrix_UB_12      -0.0376266000
_diffrn_orient_matrix_UB_13      -0.0340973000
_diffrn_orient_matrix_UB_21      -0.0980468000
_diffrn_orient_matrix_UB_22      -0.1084310000
_diffrn_orient_matrix_UB_23      -0.0180262000
_diffrn_orient_matrix_UB_31      -0.0706368000
_diffrn_orient_matrix_UB_32      0.0753516000
_diffrn_orient_matrix_UB_33      -0.0429008000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.743
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.993
_reflns_number_gt                4299
_reflns_number_total             4822
_reflns_odcompleteness_completeness 99.92
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 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    'SHELXS  (Sheldrick, 2008)'
_refine_diff_density_max         0.699
_refine_diff_density_min         -0.527
_refine_diff_density_rms         0.064
_refine_ls_abs_structure_details 
;
 Flack x determined using 1575 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.03(5)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     343
_refine_ls_number_reflns         4822
_refine_ls_number_restraints     36
_refine_ls_R_factor_all          0.0851
_refine_ls_R_factor_gt           0.0804
_refine_ls_restrained_S_all      1.332
_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)+(0.1832P)²+0.2392P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2428
_refine_ls_wR_factor_ref         0.2529
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(F) \\sim Ueq, Uanis(F4AA) \\sim Ueq, Uanis(F1) \\sim Ueq, Uanis(F3) \\sim
Ueq, Uanis(F4) \\sim Ueq, Uanis(F2) \\sim Ueq: with sigma of 0.005 and sigma
for terminal atoms of 0.01
3.a Aromatic/amide H refined with riding coordinates:
 C1AA(H1AA), C5AA(H5AA), C9AA(H9AA), C0BA(H0BA), C1BA(H1BA), C2BA(H2BA),
 C3BA(H3BA), C(H), C7BA(H7BA), C8BA(H8BA), C2CA(H2CA), C3CA(H3CA), C1(H1),
 C2AA(H2AA), C2(H2)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C0AA C -0.7552(5) -0.3853(4) -0.24876(14) 0.0579(9) Uani 1 1 d . . . . .
F0AA F -0.2713(5) -0.3192(4) -0.11343(15) 0.1043(12) Uani 1 1 d . . . . .
C1AA C -0.8048(6) -0.2663(4) -0.24794(16) 0.0625(9) Uani 1 1 d . . . . .
H1AA H -0.748781 -0.210498 -0.228972 0.075 Uiso 1 1 calc R U . . .
O2AA O -0.3722(4) -0.5240(4) -0.20853(12) 0.0856(11) Uani 1 1 d . . . . .
C3AA C -0.6513(5) -0.3243(4) -0.13657(14) 0.0553(8) Uani 1 1 d . . . . .
C4AA C -0.5622(5) -0.3936(4) -0.17436(14) 0.0583(9) Uani 1 1 d . . . . .
C5AA C -0.8400(7) -0.4663(4) -0.27844(19) 0.0727(11) Uani 1 1 d . . . . .
H5AA H -0.805955 -0.545213 -0.280042 0.087 Uiso 1 1 calc R U . . .
F1AA F -0.2545(5) -0.2950(5) -0.19240(18) 0.1194(14) Uani 1 1 d . . . . .
O O -0.4859(6) -0.5501(5) -0.28291(14) 0.1058(16) Uani 1 1 d . . . . .
C6AA C -0.4916(7) -0.5038(5) -0.24279(18) 0.0788(13) Uani 1 1 d . . . . .
C7AA C -0.4061(5) -0.4610(5) -0.16331(16) 0.0694(11) Uani 1 1 d . . . . .
C8AA C -1.0217(6) -0.3137(5) -0.30377(17) 0.0699(11) Uani 1 1 d . . . . .
C9AA C -0.6099(7) -0.2074(4) -0.12553(17) 0.0704(12) Uani 1 1 d . . . . .
H9AA H -0.521242 -0.172846 -0.141090 0.084 Uiso 1 1 calc R U . . .
C0BA C -0.4245(6) -0.5445(5) -0.11974(17) 0.0730(12) Uani 1 1 d . . . . .
H0BA H -0.450310 -0.511762 -0.088755 0.088 Uiso 1 1 calc R U . . .
C1BA C -0.9382(6) -0.2324(4) -0.27568(18) 0.0692(11) Uani 1 1 d . . . . .
H1BA H -0.971522 -0.153293 -0.275223 0.083 Uiso 1 1 calc R U . . .
F3AA F -0.1258(4) -0.4380(6) -0.1566(2) 0.1304(17) Uani 1 1 d . . . . .
C2BA C -0.4069(6) -0.6598(5) -0.12238(19) 0.0734(12) Uani 1 1 d . . . . .
H2BA H -0.376296 -0.691649 -0.153092 0.088 Uiso 1 1 calc R U . . .
C3BA C -0.7776(6) -0.3750(4) -0.1116(2) 0.0748(12) Uani 1 1 d . . . . .
H3BA H -0.804472 -0.454008 -0.117920 0.090 Uiso 1 1 calc R U . . .
C4BA C -0.2618(7) -0.3766(7) -0.1560(2) 0.0924(17) Uani 1 1 d . . . . .
C5BA C -0.6101(5) -0.4230(4) -0.22128(15) 0.0596(9) Uani 1 1 d . . . . .
C C -0.9727(7) -0.4313(5) -0.30527(19) 0.0782(13) Uani 1 1 d . . . . .
H H -1.029382 -0.486395 -0.324388 0.094 Uiso 1 1 calc R U . . .
C7BA C -0.8659(7) -0.3105(6) -0.0772(2) 0.0828(14) Uani 1 1 d . . . . .
H7BA H -0.952315 -0.345928 -0.060783 0.099 Uiso 1 1 calc R U . . .
C8BA C -0.6990(9) -0.1422(5) -0.09169(19) 0.0824(15) Uani 1 1 d . . . . .
H8BA H -0.672817 -0.062963 -0.085498 0.099 Uiso 1 1 calc R U . . .
C9BA C -0.8260(7) -0.1938(5) -0.06718(17) 0.0748(12) Uani 1 1 d . . . . .
C0CA C -1.1667(8) -0.2748(6) -0.3322(2) 0.0901(16) Uani 1 1 d . . . . .
C1CA C -0.4317(6) -0.7441(5) -0.0803(2) 0.0788(13) Uani 1 1 d . . . . .
C2CA C -0.3694(10) -0.8577(6) -0.0838(4) 0.111(2) Uani 1 1 d . . . . .
H2CA H -0.318983 -0.884050 -0.112862 0.134 Uiso 1 1 calc R U . . .
F4AA F -1.2308(11) -0.3477(7) -0.3588(4) 0.229(4) Uani 1 1 d . U . . .
C3CA C -0.5148(10) -0.7122(7) -0.0377(2) 0.1004(19) Uani 1 1 d . . . . .
H3CA H -0.556356 -0.635412 -0.035420 0.120 Uiso 1 1 calc R U . . .
F2 F -0.8344(13) -0.0748(10) 0.0033(3) 0.217(4) Uani 1 1 d . U . . .
C1 C -0.5392(16) -0.7916(10) 0.0025(4) 0.136(3) Uani 1 1 d . . . . .
H1 H -0.602901 -0.772113 0.029933 0.163 Uiso 1 1 calc R U . . .
C5CA C -0.9213(13) -0.1233(8) -0.0316(3) 0.119(3) Uani 1 1 d . . . . .
F F -1.2718(11) -0.2213(11) -0.3074(3) 0.237(4) Uani 1 1 d . U . . .
F1 F -1.1348(11) -0.1888(9) -0.3628(4) 0.221(4) Uani 1 1 d . U . . .
F3 F -0.9857(13) -0.0305(8) -0.0496(3) 0.232(4) Uani 1 1 d . U . . .
F4 F -1.0223(13) -0.1756(9) -0.0073(4) 0.260(5) Uani 1 1 d . U . . .
C2AA C -0.3858(14) -0.9346(8) -0.0402(7) 0.163(5) Uani 1 1 d . . . . .
H2AA H -0.340013 -1.010253 -0.040245 0.195 Uiso 1 1 calc R U . . .
C2 C -0.4644(18) -0.8970(12) -0.0015(5) 0.147(4) Uani 1 1 d . . . . .
H2 H -0.469485 -0.947686 0.026027 0.176 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
C0AA C1AA 1.398(6) . ?
C0AA C5AA 1.396(6) . ?
C0AA C5BA 1.473(6) . ?
F0AA C4BA 1.308(8) . ?
C1AA H1AA 0.9300 . ?
C1AA C1BA 1.386(7) . ?
O2AA C6AA 1.367(6) . ?
O2AA C7AA 1.427(5) . ?
C3AA C4AA 1.473(5) . ?
C3AA C9AA 1.387(6) . ?
C3AA C3BA 1.367(7) . ?
C4AA C7AA 1.529(6) . ?
C4AA C5BA 1.355(5) . ?
C5AA H5AA 0.9300 . ?
C5AA C 1.372(7) . ?
F1AA C4BA 1.337(8) . ?
O C6AA 1.191(6) . ?
C6AA C5BA 1.456(6) . ?
C7AA C0BA 1.501(7) . ?
C7AA C4BA 1.539(8) . ?
C8AA C1BA 1.370(7) . ?
C8AA C 1.381(8) . ?
C8AA C0CA 1.488(7) . ?
C9AA H9AA 0.9300 . ?
C9AA C8BA 1.378(7) . ?
C0BA H0BA 0.9300 . ?
C0BA C2BA 1.304(8) . ?
C1BA H1BA 0.9300 . ?
F3AA C4BA 1.323(8) . ?
C2BA H2BA 0.9300 . ?
C2BA C1CA 1.484(8) . ?
C3BA H3BA 0.9300 . ?
C3BA C7BA 1.380(7) . ?
C H 0.9300 . ?
C7BA H7BA 0.9300 . ?
C7BA C9BA 1.378(9) . ?
C8BA H8BA 0.9300 . ?
C8BA C9BA 1.369(8) . ?
C9BA C5CA 1.467(8) . ?
C0CA F4AA 1.207(8) . ?
C0CA F 1.249(10) . ?
C0CA F1 1.292(10) . ?
C1CA C2CA 1.378(9) . ?
C1CA C3CA 1.376(9) . ?
C2CA H2CA 0.9300 . ?
C2CA C2AA 1.454(15) . ?
C3CA H3CA 0.9300 . ?
C3CA C1 1.409(12) . ?
F2 C5CA 1.299(13) . ?
C1 H1 0.9300 . ?
C1 C2 1.341(18) . ?
C5CA F3 1.265(12) . ?
C5CA F4 1.212(13) . ?
C2AA H2AA 0.9300 . ?
C2AA C2 1.294(17) . ?
C2 H2 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
C1AA C0AA C5BA 120.5(4) . . ?
C5AA C0AA C1AA 118.9(4) . . ?
C5AA C0AA C5BA 120.5(4) . . ?
C0AA C1AA H1AA 120.4 . . ?
C1BA C1AA C0AA 119.3(4) . . ?
C1BA C1AA H1AA 120.4 . . ?
C6AA O2AA C7AA 109.9(3) . . ?
C9AA C3AA C4AA 121.4(4) . . ?
C3BA C3AA C4AA 120.0(4) . . ?
C3BA C3AA C9AA 118.7(4) . . ?
C3AA C4AA C7AA 123.7(3) . . ?
C5BA C4AA C3AA 127.9(4) . . ?
C5BA C4AA C7AA 107.9(4) . . ?
C0AA C5AA H5AA 119.5 . . ?
C C5AA C0AA 120.9(4) . . ?
C C5AA H5AA 119.5 . . ?
O2AA C6AA C5BA 109.2(4) . . ?
O C6AA O2AA 120.0(5) . . ?
O C6AA C5BA 130.8(5) . . ?
O2AA C7AA C4AA 104.4(3) . . ?
O2AA C7AA C0BA 111.5(4) . . ?
O2AA C7AA C4BA 105.0(4) . . ?
C4AA C7AA C4BA 112.3(4) . . ?
C0BA C7AA C4AA 111.8(4) . . ?
C0BA C7AA C4BA 111.4(4) . . ?
C1BA C8AA C 120.2(4) . . ?
C1BA C8AA C0CA 119.5(5) . . ?
C C8AA C0CA 120.3(5) . . ?
C3AA C9AA H9AA 119.7 . . ?
C8BA C9AA C3AA 120.6(5) . . ?
C8BA C9AA H9AA 119.7 . . ?
C7AA C0BA H0BA 117.8 . . ?
C2BA C0BA C7AA 124.5(5) . . ?
C2BA C0BA H0BA 117.8 . . ?
C1AA C1BA H1BA 119.5 . . ?
C8AA C1BA C1AA 120.9(4) . . ?
C8AA C1BA H1BA 119.5 . . ?
C0BA C2BA H2BA 117.4 . . ?
C0BA C2BA C1CA 125.2(5) . . ?
C1CA C2BA H2BA 117.4 . . ?
C3AA C3BA H3BA 119.5 . . ?
C3AA C3BA C7BA 121.0(5) . . ?
C7BA C3BA H3BA 119.5 . . ?
F0AA C4BA F1AA 107.3(6) . . ?
F0AA C4BA C7AA 111.5(5) . . ?
F0AA C4BA F3AA 108.6(5) . . ?
F1AA C4BA C7AA 111.3(5) . . ?
F3AA C4BA F1AA 108.0(6) . . ?
F3AA C4BA C7AA 110.0(6) . . ?
C4AA C5BA C0AA 129.1(4) . . ?
C4AA C5BA C6AA 108.5(4) . . ?
C6AA C5BA C0AA 122.4(4) . . ?
C5AA C C8AA 119.7(5) . . ?
C5AA C H 120.1 . . ?
C8AA C H 120.1 . . ?
C3BA C7BA H7BA 120.0 . . ?
C9BA C7BA C3BA 120.0(5) . . ?
C9BA C7BA H7BA 120.0 . . ?
C9AA C8BA H8BA 119.9 . . ?
C9BA C8BA C9AA 120.1(5) . . ?
C9BA C8BA H8BA 119.9 . . ?
C7BA C9BA C5CA 120.6(6) . . ?
C8BA C9BA C7BA 119.6(5) . . ?
C8BA C9BA C5CA 119.8(6) . . ?
F4AA C0CA C8AA 117.2(6) . . ?
F4AA C0CA F 109.2(8) . . ?
F4AA C0CA F1 103.0(8) . . ?
F C0CA C8AA 115.9(6) . . ?
F C0CA F1 96.9(9) . . ?
F1 C0CA C8AA 112.1(6) . . ?
C2CA C1CA C2BA 119.1(6) . . ?
C3CA C1CA C2BA 121.9(5) . . ?
C3CA C1CA C2CA 119.0(7) . . ?
C1CA C2CA H2CA 121.3 . . ?
C1CA C2CA C2AA 117.3(9) . . ?
C2AA C2CA H2CA 121.3 . . ?
C1CA C3CA H3CA 118.8 . . ?
C1CA C3CA C1 122.4(8) . . ?
C1 C3CA H3CA 118.8 . . ?
C3CA C1 H1 122.2 . . ?
C2 C1 C3CA 115.5(11) . . ?
C2 C1 H1 122.2 . . ?
F2 C5CA C9BA 113.0(9) . . ?
F3 C5CA C9BA 115.2(7) . . ?
F3 C5CA F2 99.4(9) . . ?
F4 C5CA C9BA 117.3(8) . . ?
F4 C5CA F2 101.6(9) . . ?
F4 C5CA F3 108.0(10) . . ?
C2CA C2AA H2AA 120.2 . . ?
C2 C2AA C2CA 119.5(9) . . ?
C2 C2AA H2AA 120.2 . . ?
C1 C2 H2 117.1 . . ?
C2AA C2 C1 125.8(11) . . ?
C2AA C2 H2 117.1 . . ?

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
C0AA C1AA C1BA C8AA 0.0(7) . . . . ?
C0AA C5AA C C8AA 1.3(8) . . . . ?
C1AA C0AA C5AA C -2.0(7) . . . . ?
C1AA C0AA C5BA C4AA 44.0(7) . . . . ?
C1AA C0AA C5BA C6AA -136.6(5) . . . . ?
O2AA C6AA C5BA C0AA -179.0(4) . . . . ?
O2AA C6AA C5BA C4AA 0.5(6) . . . . ?
O2AA C7AA C0BA C2BA 2.0(7) . . . . ?
O2AA C7AA C4BA F0AA -175.2(5) . . . . ?
O2AA C7AA C4BA F1AA 65.1(6) . . . . ?
O2AA C7AA C4BA F3AA -54.6(6) . . . . ?
C3AA C4AA C7AA O2AA 174.3(4) . . . . ?
C3AA C4AA C7AA C0BA 53.6(6) . . . . ?
C3AA C4AA C7AA C4BA -72.5(6) . . . . ?
C3AA C4AA C5BA C0AA 6.2(8) . . . . ?
C3AA C4AA C5BA C6AA -173.3(4) . . . . ?
C3AA C9AA C8BA C9BA 2.5(8) . . . . ?
C3AA C3BA C7BA C9BA -0.7(9) . . . . ?
C4AA C3AA C9AA C8BA 177.1(5) . . . . ?
C4AA C3AA C3BA C7BA -178.0(5) . . . . ?
C4AA C7AA C0BA C2BA 118.5(5) . . . . ?
C4AA C7AA C4BA F0AA 72.0(6) . . . . ?
C4AA C7AA C4BA F1AA -47.8(6) . . . . ?
C4AA C7AA C4BA F3AA -167.5(5) . . . . ?
C5AA C0AA C1AA C1BA 1.3(7) . . . . ?
C5AA C0AA C5BA C4AA -139.8(5) . . . . ?
C5AA C0AA C5BA C6AA 39.6(7) . . . . ?
O C6AA C5BA C0AA 1.1(10) . . . . ?
O C6AA C5BA C4AA -179.3(7) . . . . ?
C6AA O2AA C7AA C4AA -2.0(6) . . . . ?
C6AA O2AA C7AA C0BA 118.9(5) . . . . ?
C6AA O2AA C7AA C4BA -120.3(5) . . . . ?
C7AA O2AA C6AA O -179.1(6) . . . . ?
C7AA O2AA C6AA C5BA 1.0(6) . . . . ?
C7AA C4AA C5BA C0AA 177.8(4) . . . . ?
C7AA C4AA C5BA C6AA -1.7(6) . . . . ?
C7AA C0BA C2BA C1CA -177.1(4) . . . . ?
C9AA C3AA C4AA C7AA 84.2(6) . . . . ?
C9AA C3AA C4AA C5BA -105.5(6) . . . . ?
C9AA C3AA C3BA C7BA 2.0(8) . . . . ?
C9AA C8BA C9BA C7BA -1.2(9) . . . . ?
C9AA C8BA C9BA C5CA -179.4(6) . . . . ?
C0BA C7AA C4BA F0AA -54.4(6) . . . . ?
C0BA C7AA C4BA F1AA -174.1(5) . . . . ?
C0BA C7AA C4BA F3AA 66.2(6) . . . . ?
C0BA C2BA C1CA C2CA -163.0(6) . . . . ?
C0BA C2BA C1CA C3CA 16.8(9) . . . . ?
C1BA C8AA C C5AA 0.1(8) . . . . ?
C1BA C8AA C0CA F4AA 175.6(8) . . . . ?
C1BA C8AA C0CA F -52.9(11) . . . . ?
C1BA C8AA C0CA F1 56.9(9) . . . . ?
C2BA C1CA C2CA C2AA 175.5(7) . . . . ?
C2BA C1CA C3CA C1 180.0(8) . . . . ?
C3BA C3AA C4AA C7AA -95.9(6) . . . . ?
C3BA C3AA C4AA C5BA 74.5(6) . . . . ?
C3BA C3AA C9AA C8BA -2.9(7) . . . . ?
C3BA C7BA C9BA C8BA 0.3(9) . . . . ?
C3BA C7BA C9BA C5CA 178.5(6) . . . . ?
C4BA C7AA C0BA C2BA -114.9(6) . . . . ?
C5BA C0AA C1AA C1BA 177.5(4) . . . . ?
C5BA C0AA C5AA C -178.2(5) . . . . ?
C5BA C4AA C7AA O2AA 2.3(5) . . . . ?
C5BA C4AA C7AA C0BA -118.4(4) . . . . ?
C5BA C4AA C7AA C4BA 115.5(5) . . . . ?
C C8AA C1BA C1AA -0.7(8) . . . . ?
C C8AA C0CA F4AA -5.1(11) . . . . ?
C C8AA C0CA F 126.3(9) . . . . ?
C C8AA C0CA F1 -123.8(8) . . . . ?
C7BA C9BA C5CA F2 126.6(10) . . . . ?
C7BA C9BA C5CA F3 -120.1(10) . . . . ?
C7BA C9BA C5CA F4 8.8(14) . . . . ?
C8BA C9BA C5CA F2 -55.2(11) . . . . ?
C8BA C9BA C5CA F3 58.1(12) . . . . ?
C8BA C9BA C5CA F4 -173.0(10) . . . . ?
C0CA C8AA C1BA C1AA 178.6(5) . . . . ?
C0CA C8AA C C5AA -179.2(5) . . . . ?
C1CA C2CA C2AA C2 3.8(15) . . . . ?
C1CA C3CA C1 C2 5.5(15) . . . . ?
C2CA C1CA C3CA C1 -0.2(11) . . . . ?
C2CA C2AA C2 C1 2(2) . . . . ?
C3CA C1CA C2CA C2AA -4.4(10) . . . . ?
C3CA C1 C2 C2AA -6(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 3.958
_oxdiff_exptl_absorpt_empirical_full_min 0.643
