# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2023

####################################################################### 
# 
# 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_stu1026
_database_code_depnum_ccdc_archive 'CCDC 2164789'
loop_
_audit_author_name
_audit_author_address
'Ryota Sato'
;University of Tsukuba
Japan
;
_audit_update_record             
;
2022-04-06 deposited with the CCDC.	2023-05-04 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C22 H6 F10'
_chemical_formula_moiety         'C22 H6 F10'
_chemical_formula_weight         460.27
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
_space_group_IT_number           14
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 1/2-X,1/2+Y,1/2-Z
3 -X,-Y,-Z
4 -1/2+X,-1/2-Y,-1/2+Z
#------------------------------------------------------------------------------
_cell_length_a                   13.4090(15)
_cell_length_b                   6.5074(7)
_cell_length_c                   19.584(2)
_cell_angle_alpha                90.0000
_cell_angle_beta                 97.3500(10)
_cell_angle_gamma                90.0000
_cell_volume                     1694.8(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3399
_cell_measurement_theta_min      3.06
_cell_measurement_theta_max      27.12
_cell_measurement_temperature    120
#------------------------------------------------------------------------------
_exptl_crystal_description       nONE
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.216
_exptl_crystal_size_mid          0.069
_exptl_crystal_size_min          0.025
_exptl_crystal_density_diffrn    1.804
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             912.00
_exptl_absorpt_coefficient_mu    0.182
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   
; 
SADABS V2008/1 (Bruker AXS) 
;
_exptl_absorpt_correction_T_min  0.7016
_exptl_absorpt_correction_T_max  0.7455

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      120
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_radiation_source         'Bruker TXS fine-focus rotating anode'
_diffrn_radiation_monochromator  'Bruker Helios multilayer confocal mirror'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 8.333
_diffrn_reflns_number            9308
_diffrn_reflns_av_unetI/netI     0.0273
_diffrn_reflns_av_R_equivalents  0.0217
_diffrn_reflns_theta_max         27.104
_diffrn_reflns_theta_min         1.742
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       20
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             3724
_reflns_number_gt                2982
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0459
_refine_ls_R_factor_gt           0.0337
_refine_ls_wR_factor_ref         0.0926
_refine_ls_wR_factor_gt          0.0840
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         3724
_refine_ls_number_parameters     289
_refine_ls_goodness_of_fit_ref   1.004
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0440P)²+0.8430P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         0.30
_refine_diff_density_min         -0.25
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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 for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
F F 0.0171 0.0103
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.24835(7) 1.22025(15) -0.04897(5) 0.0259(2) Uani 1 1 d . . . . .
F2 F 0.09341(7) 1.26726(15) -0.14886(5) 0.0294(2) Uani 1 1 d . . . . .
F3 F 0.05117(7) 0.97374(16) -0.24617(5) 0.0281(2) Uani 1 1 d . . . . .
F4 F 0.17087(7) 0.63459(16) -0.24561(5) 0.0299(3) Uani 1 1 d . . . . .
F5 F 0.32740(7) 0.58693(15) -0.14777(5) 0.0283(2) Uani 1 1 d . . . . .
F6 F 0.25777(7) 0.36464(14) 0.08780(5) 0.0238(2) Uani 1 1 d . . . . .
F7 F 0.43515(7) 0.27268(16) 0.16135(5) 0.0307(3) Uani 1 1 d . . . . .
F8 F 0.46077(7) -0.08614(16) 0.23021(5) 0.0302(2) Uani 1 1 d . . . . .
F9 F 0.30804(7) -0.36396(15) 0.22268(5) 0.0276(2) Uani 1 1 d . . . . .
F10 F 0.12835(7) -0.27215(15) 0.15309(5) 0.0249(2) Uani 1 1 d . . . . .
C1 C 0.37991(11) 0.8723(2) -0.03870(8) 0.0181(3) Uani 1 1 d . . . . .
C2 C 0.37849(12) 0.7047(3) 0.00338(9) 0.0215(3) Uani 1 1 d . . . . .
H1A H 0.326679 0.609347 -0.004928 0.026 Uiso 1 1 calc R U . . .
C3 C 0.45440(12) 0.6748(3) 0.05902(9) 0.0223(3) Uani 1 1 d . . . . .
H2 H 0.451782 0.561068 0.087499 0.027 Uiso 1 1 calc R U . . .
C4 C 0.46831(12) 1.1891(3) -0.07157(8) 0.0206(3) Uani 1 1 d . . . . .
H3 H 0.419414 1.209542 -0.109117 0.025 Uiso 1 1 calc R U . . .
C5 C 0.46132(11) 1.0165(2) -0.02810(8) 0.0169(3) Uani 1 1 d . . . . .
C6 C 0.29525(11) 0.9033(2) -0.09525(8) 0.0179(3) Uani 1 1 d . . . . .
C7 C 0.27096(12) 0.7579(2) -0.14641(8) 0.0201(3) Uani 1 1 d . . . . .
C8 C 0.19034(12) 0.7794(2) -0.19701(8) 0.0201(3) Uani 1 1 d . . . . .
C9 C 0.12997(12) 0.9513(3) -0.19784(8) 0.0203(3) Uani 1 1 d . . . . .
C10 C 0.15161(12) 1.1003(2) -0.14830(8) 0.0202(3) Uani 1 1 d . . . . .
C11 C 0.23257(12) 1.0741(2) -0.09791(8) 0.0194(3) Uani 1 1 d . . . . .
C12 C 0.08802(11) 0.0989(2) 0.07528(8) 0.0166(3) Uani 1 1 d . . . . .
C13 C 0.03807(12) 0.2728(2) 0.09156(8) 0.0193(3) Uani 1 1 d . . . . .
H4 H 0.065817 0.355380 0.127867 0.023 Uiso 1 1 calc R U . . .
C14 C -0.05446(12) 0.3275(2) 0.05398(8) 0.0199(3) Uani 1 1 d . . . . .
H5 H -0.087544 0.445589 0.065628 0.024 Uiso 1 1 calc R U . . .
C15 C 0.09593(12) -0.2084(2) -0.00055(8) 0.0179(3) Uani 1 1 d . . . . .
H6 H 0.157520 -0.245687 0.023612 0.021 Uiso 1 1 calc R U . . .
C16 C 0.04676(11) -0.0283(2) 0.01891(8) 0.0159(3) Uani 1 1 d . . . . .
C17 C 0.18677(11) 0.0468(2) 0.11584(8) 0.0173(3) Uani 1 1 d . . . . .
C18 C 0.26722(12) 0.1827(2) 0.12054(8) 0.0185(3) Uani 1 1 d . . . . .
C19 C 0.35895(12) 0.1391(3) 0.15837(8) 0.0217(3) Uani 1 1 d . . . . .
C20 C 0.37271(12) -0.0450(3) 0.19293(8) 0.0212(3) Uani 1 1 d . . . . .
C21 C 0.29484(12) -0.1840(2) 0.18921(8) 0.0195(3) Uani 1 1 d . . . . .
C22 C 0.20358(12) -0.1363(2) 0.15215(8) 0.0184(3) Uani 1 1 d . . . . .


#==============================================================================
_computing_data_collection       Unknown
_computing_cell_refinement       Unknown
_computing_data_reduction        Unknown
_computing_structure_solution    'SIR92 (Altomare, et al., 1994)'
_computing_structure_refinement  'SHELXL Version 2018/3 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.3 (Rigaku, 2019)'
_computing_molecular_graphics    'CrystalStructure 4.3'

#==============================================================================
# MOLECULAR GEOMETRY

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C11 1.3473(18) . ?
F2 C10 1.3368(18) . ?
F3 C9 1.3333(18) . ?
F4 C8 1.3410(18) . ?
F5 C7 1.3479(18) . ?
F6 C18 1.3446(18) . ?
F7 C19 1.3369(18) . ?
F8 C20 1.3335(18) . ?
F9 C21 1.3428(18) . ?
F10 C22 1.3432(17) . ?
C1 C2 1.369(2) . ?
C1 C5 1.434(2) . ?
C1 C6 1.495(2) . ?
C2 C3 1.406(2) . ?
C2 H1A 0.9300 . ?
C3 C4 1.361(2) 3_675 ?
C3 H2 0.9300 . ?
C4 C5 1.420(2) . ?
C4 H3 0.9300 . ?
C5 C5 1.429(3) 3_675 ?
C6 C7 1.386(2) . ?
C6 C11 1.391(2) . ?
C7 C8 1.377(2) . ?
C8 C9 1.380(2) . ?
C9 C10 1.376(2) . ?
C10 C11 1.381(2) . ?
C12 C13 1.373(2) . ?
C12 C16 1.433(2) . ?
C12 C17 1.493(2) . ?
C13 C14 1.405(2) . ?
C13 H4 0.9300 . ?
C14 C15 1.362(2) 3 ?
C14 H5 0.9300 . ?
C15 C16 1.421(2) . ?
C15 H6 0.9300 . ?
C16 C16 1.421(3) 3 ?
C17 C22 1.391(2) . ?
C17 C18 1.389(2) . ?
C18 C19 1.382(2) . ?
C19 C20 1.377(2) . ?
C20 C21 1.376(2) . ?
C21 C22 1.376(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C5 120.21(14) . . ?
C2 C1 C6 119.08(14) . . ?
C5 C1 C6 120.71(14) . . ?
C1 C2 C3 120.82(15) . . ?
C1 C2 H1A 119.6 . . ?
C3 C2 H1A 119.6 . . ?
C4 C3 C2 120.58(15) 3_675 . ?
C4 C3 H2 119.7 3_675 . ?
C2 C3 H2 119.7 . . ?
C3 C4 C5 120.91(15) 3_675 . ?
C3 C4 H3 119.5 3_675 . ?
C5 C4 H3 119.5 . . ?
C4 C5 C5 118.91(18) . 3_675 ?
C4 C5 C1 122.57(14) . . ?
C5 C5 C1 118.53(17) 3_675 . ?
C7 C6 C11 115.69(14) . . ?
C7 C6 C1 121.96(14) . . ?
C11 C6 C1 122.27(14) . . ?
F5 C7 C8 117.43(14) . . ?
F5 C7 C6 119.80(14) . . ?
C8 C7 C6 122.77(15) . . ?
F4 C8 C7 120.21(14) . . ?
F4 C8 C9 120.05(14) . . ?
C7 C8 C9 119.74(15) . . ?
F3 C9 C10 120.00(15) . . ?
F3 C9 C8 120.49(15) . . ?
C10 C9 C8 119.51(15) . . ?
F2 C10 C9 119.78(14) . . ?
F2 C10 C11 120.72(14) . . ?
C9 C10 C11 119.50(15) . . ?
F1 C11 C10 117.30(14) . . ?
F1 C11 C6 119.89(14) . . ?
C10 C11 C6 122.79(15) . . ?
C13 C12 C16 120.20(14) . . ?
C13 C12 C17 119.28(14) . . ?
C16 C12 C17 120.50(14) . . ?
C12 C13 C14 120.76(14) . . ?
C12 C13 H4 119.6 . . ?
C14 C13 H4 119.6 . . ?
C15 C14 C13 120.29(15) 3 . ?
C15 C14 H5 119.9 3 . ?
C13 C14 H5 119.9 . . ?
C14 C15 C16 121.18(15) 3 . ?
C14 C15 H6 119.4 3 . ?
C16 C15 H6 119.4 . . ?
C16 C16 C15 118.86(17) 3 . ?
C16 C16 C12 118.71(18) 3 . ?
C15 C16 C12 122.44(14) . . ?
C22 C17 C18 115.97(14) . . ?
C22 C17 C12 122.74(14) . . ?
C18 C17 C12 121.27(14) . . ?
F6 C18 C19 117.36(14) . . ?
F6 C18 C17 120.27(14) . . ?
C19 C18 C17 122.37(15) . . ?
F7 C19 C18 120.86(15) . . ?
F7 C19 C20 119.38(14) . . ?
C18 C19 C20 119.76(15) . . ?
F8 C20 C21 120.65(15) . . ?
F8 C20 C19 119.82(15) . . ?
C21 C20 C19 119.52(15) . . ?
F9 C21 C22 120.46(14) . . ?
F9 C21 C20 119.71(14) . . ?
C22 C21 C20 119.83(15) . . ?
F10 C22 C21 117.59(14) . . ?
F10 C22 C17 119.86(14) . . ?
C21 C22 C17 122.53(14) . . ?

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
C5 C1 C2 C3 2.3(2) . . . . ?
C6 C1 C2 C3 -177.17(14) . . . . ?
C1 C2 C3 C4 -0.9(3) . . . 3_675 ?
C3 C4 C5 C5 -2.0(3) 3_675 . . 3_675 ?
C3 C4 C5 C1 178.58(15) 3_675 . . . ?
C2 C1 C5 C4 177.85(15) . . . . ?
C6 C1 C5 C4 -2.6(2) . . . . ?
C2 C1 C5 C5 -1.6(3) . . . 3_675 ?
C6 C1 C5 C5 177.91(16) . . . 3_675 ?
C2 C1 C6 C7 -58.6(2) . . . . ?
C5 C1 C6 C7 121.85(17) . . . . ?
C2 C1 C6 C11 117.85(17) . . . . ?
C5 C1 C6 C11 -61.7(2) . . . . ?
C11 C6 C7 F5 -179.80(13) . . . . ?
C1 C6 C7 F5 -3.1(2) . . . . ?
C11 C6 C7 C8 0.1(2) . . . . ?
C1 C6 C7 C8 176.83(15) . . . . ?
F5 C7 C8 F4 -0.7(2) . . . . ?
C6 C7 C8 F4 179.42(14) . . . . ?
F5 C7 C8 C9 179.81(14) . . . . ?
C6 C7 C8 C9 -0.1(2) . . . . ?
F4 C8 C9 F3 1.0(2) . . . . ?
C7 C8 C9 F3 -179.50(14) . . . . ?
F4 C8 C9 C10 -179.03(14) . . . . ?
C7 C8 C9 C10 0.5(2) . . . . ?
F3 C9 C10 F2 0.0(2) . . . . ?
C8 C9 C10 F2 179.98(14) . . . . ?
F3 C9 C10 C11 179.09(14) . . . . ?
C8 C9 C10 C11 -0.9(2) . . . . ?
F2 C10 C11 F1 1.7(2) . . . . ?
C9 C10 C11 F1 -177.44(14) . . . . ?
F2 C10 C11 C6 -179.94(14) . . . . ?
C9 C10 C11 C6 1.0(2) . . . . ?
C7 C6 C11 F1 177.81(13) . . . . ?
C1 C6 C11 F1 1.1(2) . . . . ?
C7 C6 C11 C10 -0.6(2) . . . . ?
C1 C6 C11 C10 -177.25(15) . . . . ?
C16 C12 C13 C14 0.8(2) . . . . ?
C17 C12 C13 C14 179.31(14) . . . . ?
C12 C13 C14 C15 -0.2(2) . . . 3 ?
C14 C15 C16 C16 -0.7(3) 3 . . 3 ?
C14 C15 C16 C12 179.35(14) 3 . . . ?
C13 C12 C16 C16 -0.7(3) . . . 3 ?
C17 C12 C16 C16 -179.18(16) . . . 3 ?
C13 C12 C16 C15 179.26(14) . . . . ?
C17 C12 C16 C15 0.8(2) . . . . ?
C13 C12 C17 C22 120.73(17) . . . . ?
C16 C12 C17 C22 -60.8(2) . . . . ?
C13 C12 C17 C18 -57.9(2) . . . . ?
C16 C12 C17 C18 120.64(17) . . . . ?
C22 C17 C18 F6 -179.30(13) . . . . ?
C12 C17 C18 F6 -0.6(2) . . . . ?
C22 C17 C18 C19 0.6(2) . . . . ?
C12 C17 C18 C19 179.25(15) . . . . ?
F6 C18 C19 F7 -0.7(2) . . . . ?
C17 C18 C19 F7 179.44(14) . . . . ?
F6 C18 C19 C20 179.99(14) . . . . ?
C17 C18 C19 C20 0.1(2) . . . . ?
F7 C19 C20 F8 1.6(2) . . . . ?
C18 C19 C20 F8 -179.10(14) . . . . ?
F7 C19 C20 C21 -179.14(14) . . . . ?
C18 C19 C20 C21 0.2(2) . . . . ?
F8 C20 C21 F9 -0.9(2) . . . . ?
C19 C20 C21 F9 179.82(14) . . . . ?
F8 C20 C21 C22 178.08(14) . . . . ?
C19 C20 C21 C22 -1.2(2) . . . . ?
F9 C21 C22 F10 2.5(2) . . . . ?
C20 C21 C22 F10 -176.51(14) . . . . ?
F9 C21 C22 C17 -179.05(14) . . . . ?
C20 C21 C22 C17 2.0(2) . . . . ?
C18 C17 C22 F10 176.83(13) . . . . ?
C12 C17 C22 F10 -1.8(2) . . . . ?
C18 C17 C22 C21 -1.6(2) . . . . ?
C12 C17 C22 C21 179.71(14) . . . . ?


#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.


####################################################################### 
# 
# 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_stu1052
_database_code_depnum_ccdc_archive 'CCDC 2234487'
loop_
_audit_author_name
_audit_author_address
'Ryota Sato'
;University of Tsukuba
Japan
;
_audit_update_record             
;
2023-01-05 deposited with the CCDC.	2023-05-04 downloaded from the CCDC.
;
_chemical_formula_moiety         'C38 H22 F10'
#==============================================================================
# CHEMICAL DATA
_chemical_formula_sum            'C38 H22 F10'
_chemical_formula_weight         668.58
_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 0.0033 0.0016
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
F F 0.0171 0.0103
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,1/2+Y,1/2-Z
3 -X,-Y,-Z
4 +X,-1/2-Y,-1/2+Z

#------------------------------------------------------------------------------
_cell_length_a                   12.909(8)
_cell_length_b                   8.301(5)
_cell_length_c                   15.210(9)
_cell_angle_alpha                90.0000
_cell_angle_beta                 114.905(7)
_cell_angle_gamma                90.0000
_cell_volume                     1478.3(15)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1253
_cell_measurement_temperature    120
_cell_measurement_theta_max      24.01
_cell_measurement_theta_min      2.72
_exptl_absorpt_coefficient_mu    0.130
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.4204
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   
;
SADABS V2008/1 (Bruker AXS) 
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.502
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
#------------------------------------------------------------------------------
_exptl_crystal_description       nONE
_exptl_crystal_F_000             680.00
_exptl_crystal_size_max          0.550
_exptl_crystal_size_mid          0.115
_exptl_crystal_size_min          0.024
_diffrn_reflns_av_R_equivalents  0.0542
_diffrn_reflns_av_unetI/netI     0.0802
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            7888
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.104
_diffrn_reflns_theta_min         1.739
#==============================================================================
# EXPERIMENTAL DATA
_diffrn_ambient_temperature      120
_diffrn_detector_area_resol_mean 8.333
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  'Bruker Helios multilayer confocal mirror'
_diffrn_radiation_source         'Bruker TXS fine-focus rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count .
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1809
_reflns_number_total             3254
_reflns_threshold_expression     F²>2.0σ(F²)
_computing_cell_refinement       Unknown
#==============================================================================
_computing_data_collection       Unknown
_computing_data_reduction        Unknown
_computing_molecular_graphics    'CrystalStructure 4.3'
_computing_publication_material  'CrystalStructure 4.3 (Rigaku, 2019)'
_computing_structure_refinement  'SHELXL Version 2018/3 (Sheldrick, 2008)'
_computing_structure_solution    'SIR92 (Altomare, et al., 1994)'
_refine_diff_density_max         0.34
_refine_diff_density_min         -0.35
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.983
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_parameters     241
_refine_ls_number_reflns         3254
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1144
_refine_ls_R_factor_gt           0.0585
_refine_ls_shift/su_max          0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0878P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1435
_refine_ls_wR_factor_ref         0.1717
#==============================================================================
# REFINEMENT DATA
_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.71180(16) 0.91585(19) 0.45651(14) 0.0452(5) Uani 1 1 d . . . . .
F2 F 0.55220(18) 1.1097(2) 0.33035(17) 0.0608(6) Uani 1 1 d . . . . .
F3 F 0.48790(17) 1.0738(3) 0.13690(17) 0.0723(7) Uani 1 1 d . . . . .
F4 F 0.59933(18) 0.8587(2) 0.07159(14) 0.0616(6) Uani 1 1 d . . . . .
F5 F 0.76767(16) 0.6777(2) 0.19673(12) 0.0463(5) Uani 1 1 d . . . . .
C1 C 0.8778(2) 0.4873(3) 0.5372(2) 0.0254(6) Uani 1 1 d . . . . .
C2 C 0.8014(2) 0.5895(3) 0.4704(2) 0.0274(6) Uani 1 1 d . . . . .
H1A H 0.730512 0.605635 0.471141 0.033 Uiso 1 1 calc R U . . .
C3 C 0.8274(2) 0.6715(3) 0.40022(19) 0.0245(6) Uani 1 1 d . . . . .
C4 C 1.0682(2) 0.3530(3) 0.6017(2) 0.0254(6) Uani 1 1 d . . . . .
H2A H 1.050417 0.298028 0.646855 0.031 Uiso 1 1 calc R U . . .
C5 C 0.9874(2) 0.4609(3) 0.53595(19) 0.0238(6) Uani 1 1 d . . . . .
C6 C 0.8479(2) 0.4065(3) 0.6118(2) 0.0270(6) Uani 1 1 d . . . . .
C7 C 0.9131(2) 0.4351(3) 0.7102(2) 0.0290(6) Uani 1 1 d . . . . .
H3 H 0.975468 0.504382 0.729794 0.035 Uiso 1 1 calc R U . . .
C8 C 0.8846(3) 0.3593(3) 0.7797(2) 0.0362(8) Uani 1 1 d . . . . .
C9 C 0.7918(3) 0.2563(3) 0.7477(3) 0.0395(8) Uani 1 1 d . . . . .
H4 H 0.773711 0.203772 0.793464 0.047 Uiso 1 1 calc R U . . .
C10 C 0.7247(3) 0.2282(3) 0.6504(3) 0.0371(8) Uani 1 1 d . . . . .
C11 C 0.7540(2) 0.3055(3) 0.5820(2) 0.0310(7) Uani 1 1 d . . . . .
H5 H 0.709965 0.288787 0.516241 0.037 Uiso 1 1 calc R U . . .
C12 C 0.9547(4) 0.3888(5) 0.8843(3) 0.0478(9) Uani 1 1 d . . . . .
C13 C 0.6203(4) 0.1195(4) 0.6148(4) 0.0523(10) Uani 1 1 d . . . . .
C14 C 0.7426(2) 0.7828(3) 0.3308(2) 0.0293(7) Uani 1 1 d . . . . .
C15 C 0.6844(2) 0.8975(3) 0.3614(2) 0.0316(7) Uani 1 1 d . . . . .
C16 C 0.6021(3) 0.9964(3) 0.2974(3) 0.0416(8) Uani 1 1 d . . . . .
C17 C 0.5720(3) 0.9811(4) 0.1998(3) 0.0471(9) Uani 1 1 d . . . . .
C18 C 0.6280(3) 0.8721(4) 0.1668(2) 0.0412(8) Uani 1 1 d . . . . .
C19 C 0.7135(3) 0.7805(3) 0.2323(2) 0.0351(7) Uani 1 1 d . . . . .
H6 H 0.974(4) 0.491(5) 0.903(3) 0.086(14) Uiso 1 1 d . . . . .
H7 H 1.016(3) 0.316(5) 0.908(3) 0.060(11) Uiso 1 1 d . . . . .
H8 H 0.911(5) 0.358(7) 0.916(4) 0.14(2) Uiso 1 1 d . . . . .
H9 H 0.603(4) 0.089(4) 0.664(3) 0.084(14) Uiso 1 1 d . . . . .
H10 H 0.630(3) 0.021(5) 0.574(3) 0.067(11) Uiso 1 1 d . . . . .
H11 H 0.541(4) 0.178(5) 0.575(3) 0.079(12) Uiso 1 1 d . . . . .


#==============================================================================
# MOLECULAR GEOMETRY
_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C15 1.345(3) . ?
F2 C16 1.350(3) . ?
F3 C17 1.345(4) . ?
F4 C18 1.340(4) . ?
F5 C19 1.353(3) . ?
C1 C2 1.371(4) . ?
C1 C5 1.439(4) . ?
C1 C6 1.501(4) . ?
C2 H1A 0.9300 . ?
C2 C3 1.420(4) . ?
C3 C4 1.375(4) 3_766 ?
C3 C14 1.482(4) . ?
C4 H2A 0.9300 . ?
C4 C5 1.419(4) . ?
C5 C5 1.423(5) 3_766 ?
C6 C7 1.394(4) . ?
C6 C11 1.384(4) . ?
C7 H3 0.9300 . ?
C7 C8 1.407(4) . ?
C8 C9 1.383(4) . ?
C8 C12 1.482(5) . ?
C9 H4 0.9300 . ?
C9 C10 1.384(5) . ?
C10 C11 1.402(4) . ?
C10 C13 1.520(5) . ?
C11 H5 0.9300 . ?
C12 H6 0.89(4) . ?
C12 H7 0.94(4) . ?
C12 H8 0.93(6) . ?
C13 H9 0.91(4) . ?
C13 H10 1.06(4) . ?
C13 H11 1.06(4) . ?
C14 C15 1.408(4) . ?
C14 C19 1.382(4) . ?
C15 C16 1.370(4) . ?
C16 C17 1.374(5) . ?
C17 C18 1.378(5) . ?
C18 C19 1.365(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C5 119.2(2) . . ?
C2 C1 C6 120.2(2) . . ?
C5 C1 C6 120.6(2) . . ?
C1 C2 H1A 119.0 . . ?
C1 C2 C3 122.0(2) . . ?
C3 C2 H1A 119.0 . . ?
C2 C3 C14 119.8(2) . . ?
C4 C3 C2 119.3(2) 3_766 . ?
C4 C3 C14 120.9(2) 3_766 . ?
C3 C4 H2A 119.5 3_766 . ?
C3 C4 C5 121.0(2) 3_766 . ?
C5 C4 H2A 119.5 . . ?
C4 C5 C1 121.5(2) . . ?
C4 C5 C5 119.4(3) . 3_766 ?
C5 C5 C1 119.0(3) 3_766 . ?
C7 C6 C1 120.2(2) . . ?
C11 C6 C1 119.5(3) . . ?
C11 C6 C7 120.3(2) . . ?
C6 C7 H3 120.0 . . ?
C6 C7 C8 120.0(3) . . ?
C8 C7 H3 120.0 . . ?
C7 C8 C12 119.9(3) . . ?
C9 C8 C7 118.3(3) . . ?
C9 C8 C12 121.8(3) . . ?
C8 C9 H4 118.7 . . ?
C8 C9 C10 122.6(3) . . ?
C10 C9 H4 118.7 . . ?
C9 C10 C11 118.3(3) . . ?
C9 C10 C13 122.8(3) . . ?
C11 C10 C13 118.9(3) . . ?
C6 C11 C10 120.5(3) . . ?
C6 C11 H5 119.7 . . ?
C10 C11 H5 119.7 . . ?
C8 C12 H6 118(3) . . ?
C8 C12 H7 110(2) . . ?
C8 C12 H8 107(4) . . ?
H6 C12 H7 114(4) . . ?
H6 C12 H8 104(4) . . ?
H7 C12 H8 103(4) . . ?
C10 C13 H9 111(3) . . ?
C10 C13 H10 111.3(19) . . ?
C10 C13 H11 115(2) . . ?
H9 C13 H10 113(3) . . ?
H9 C13 H11 95(3) . . ?
H10 C13 H11 110(3) . . ?
C15 C14 C3 121.6(3) . . ?
C19 C14 C3 123.0(2) . . ?
C19 C14 C15 115.4(3) . . ?
F1 C15 C14 119.8(3) . . ?
F1 C15 C16 118.0(3) . . ?
C16 C15 C14 122.2(3) . . ?
F2 C16 C15 120.2(3) . . ?
F2 C16 C17 120.2(3) . . ?
C15 C16 C17 119.6(3) . . ?
F3 C17 C16 119.5(3) . . ?
F3 C17 C18 120.5(3) . . ?
C16 C17 C18 120.0(3) . . ?
F4 C18 C17 119.9(3) . . ?
F4 C18 C19 120.9(3) . . ?
C19 C18 C17 119.1(3) . . ?
F5 C19 C14 119.5(3) . . ?
F5 C19 C18 117.0(3) . . ?
C18 C19 C14 123.4(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
F1 C15 C16 F2 0.9(4) . . . . ?
F1 C15 C16 C17 -180.0(3) . . . . ?
F2 C16 C17 F3 -3.6(4) . . . . ?
F2 C16 C17 C18 176.0(3) . . . . ?
F3 C17 C18 F4 0.4(4) . . . . ?
F3 C17 C18 C19 179.6(3) . . . . ?
F4 C18 C19 F5 0.6(4) . . . . ?
F4 C18 C19 C14 -176.4(3) . . . . ?
C1 C2 C3 C4 0.6(4) . . . 3_766 ?
C1 C2 C3 C14 -178.9(2) . . . . ?
C1 C6 C7 C8 179.9(2) . . . . ?
C1 C6 C11 C10 179.7(2) . . . . ?
C2 C1 C5 C4 -178.3(2) . . . . ?
C2 C1 C5 C5 -1.3(4) . . . 3_766 ?
C2 C1 C6 C7 -118.6(3) . . . . ?
C2 C1 C6 C11 60.3(3) . . . . ?
C2 C3 C14 C15 46.1(4) . . . . ?
C2 C3 C14 C19 -132.8(3) . . . . ?
C3 C4 C5 C1 179.9(2) 3_766 . . . ?
C3 C4 C5 C5 3.0(4) 3_766 . . 3_766 ?
C3 C14 C15 F1 5.1(4) . . . . ?
C3 C14 C15 C16 -177.1(2) . . . . ?
C3 C14 C19 F5 -3.2(4) . . . . ?
C3 C14 C19 C18 173.7(2) . . . . ?
C4 C3 C14 C15 -133.4(3) 3_766 . . . ?
C4 C3 C14 C19 47.7(4) 3_766 . . . ?
C5 C1 C2 C3 -0.5(4) . . . . ?
C5 C1 C6 C7 60.3(3) . . . . ?
C5 C1 C6 C11 -120.8(3) . . . . ?
C6 C1 C2 C3 178.4(2) . . . . ?
C6 C1 C5 C4 2.8(4) . . . . ?
C6 C1 C5 C5 179.8(3) . . . 3_766 ?
C6 C7 C8 C9 0.4(4) . . . . ?
C6 C7 C8 C12 179.4(3) . . . . ?
C7 C6 C11 C10 -1.4(4) . . . . ?
C7 C8 C9 C10 -1.6(4) . . . . ?
C8 C9 C10 C11 1.2(4) . . . . ?
C8 C9 C10 C13 -177.9(3) . . . . ?
C9 C10 C11 C6 0.3(4) . . . . ?
C11 C6 C7 C8 1.0(4) . . . . ?
C12 C8 C9 C10 179.5(3) . . . . ?
C13 C10 C11 C6 179.4(3) . . . . ?
C14 C15 C16 F2 -177.0(2) . . . . ?
C14 C15 C16 C17 2.1(4) . . . . ?
C15 C14 C19 F5 177.9(2) . . . . ?
C15 C14 C19 C18 -5.3(4) . . . . ?
C15 C16 C17 F3 177.3(2) . . . . ?
C15 C16 C17 C18 -3.1(4) . . . . ?
C16 C17 C18 F4 -179.2(3) . . . . ?
C16 C17 C18 C19 -0.1(4) . . . . ?
C17 C18 C19 F5 -178.6(3) . . . . ?
C17 C18 C19 C14 4.5(4) . . . . ?
C19 C14 C15 F1 -175.9(2) . . . . ?
C19 C14 C15 C16 1.9(4) . . . . ?

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.
####################################################################### 
# 
# 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_stu1110
_database_code_depnum_ccdc_archive 'CCDC 2234489'
loop_
_audit_author_name
_audit_author_address
'Ryota Sato'
;University of Tsukuba
Japan
;
_audit_update_record             
;
2023-01-05 deposited with the CCDC.	2023-05-04 downloaded from the CCDC.
;
_chemical_formula_moiety         'C42 H24 F10'
#==============================================================================
# CHEMICAL DATA
_chemical_formula_sum            'C42 H24 F10'
_chemical_formula_weight         718.64
_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 0.0033 0.0016
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
F F 0.0171 0.0103
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,-Y,-Z

#------------------------------------------------------------------------------
_cell_length_a                   8.0202
_cell_length_b                   14.0657
_cell_length_c                   14.6150
_cell_angle_alpha                82.4280
_cell_angle_beta                 85.8090
_cell_angle_gamma                79.9520
_cell_volume                     1607.1494
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1900
_cell_measurement_temperature    120
_cell_measurement_theta_max      26.99
_cell_measurement_theta_min      2.75
_exptl_absorpt_coefficient_mu    0.126
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   
; 
SADABS V2008/1 (Bruker AXS) 
;
_exptl_absorpt_correction_T_min  0.6001
_exptl_absorpt_correction_T_max  0.7455

_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.485
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
#------------------------------------------------------------------------------
_exptl_crystal_description       nONE
_exptl_crystal_F_000             732.00
_exptl_crystal_size_max          0.295
_exptl_crystal_size_mid          0.040
_exptl_crystal_size_min          0.021
_diffrn_reflns_av_R_equivalents  0.0245
_diffrn_reflns_av_unetI/netI     0.0699
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.969
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            9184
_diffrn_reflns_point_group_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.969
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.102
_diffrn_reflns_theta_min         1.407
#==============================================================================
# EXPERIMENTAL DATA
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.969
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_radiation_source         'Bruker TXS fine-focus rotating anode'
_diffrn_radiation_monochromator  'Bruker Helios multilayer confocal mirror'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_ambient_temperature      120
_diffrn_detector_area_resol_mean 8.333
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count .
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4421
_reflns_number_total             6863
_reflns_threshold_expression     F²>2.0σ(F²)
_computing_cell_refinement       Unknown
#==============================================================================
_computing_data_collection       Unknown
_computing_data_reduction        Unknown
_computing_molecular_graphics    'CrystalStructure 4.3'
_computing_publication_material  'CrystalStructure 4.3 (Rigaku, 2019)'
_computing_structure_refinement  'SHELXL Version 2018/3 (Sheldrick, 2008)'
_computing_structure_solution    'SIR2014 (Burla, et al., 2014)'
_refine_diff_density_max         0.45
_refine_diff_density_min         -0.49
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     469
_refine_ls_number_reflns         6863
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0965
_refine_ls_R_factor_gt           0.0569
_refine_ls_shift/su_max          0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0673P)²+0.2916P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1337
_refine_ls_wR_factor_ref         0.1541
#==============================================================================
# REFINEMENT DATA
_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F -0.28058(19) 0.23937(10) 0.33386(10) 0.0257(4) Uani 1 1 d . . . . .
F2 F -0.3331(2) 0.13109(11) 0.20590(12) 0.0373(4) Uani 1 1 d . . . . .
F3 F -0.2534(3) 0.18308(13) 0.02489(13) 0.0505(5) Uani 1 1 d . . . . .
F4 F -0.1173(3) 0.34778(13) -0.02725(11) 0.0456(5) Uani 1 1 d . . . . .
F5 F -0.0563(2) 0.45615(11) 0.09942(10) 0.0286(4) Uani 1 1 d . . . . .
F6 F 0.4164(2) 0.76622(11) 0.15456(10) 0.0282(4) Uani 1 1 d . . . . .
F7 F 0.3317(2) 0.95019(11) 0.07483(11) 0.0403(5) Uani 1 1 d . . . . .
F8 F 0.0895(2) 1.07638(11) 0.15583(12) 0.0428(5) Uani 1 1 d . . . . .
F9 F -0.0525(2) 1.02065(11) 0.32529(13) 0.0375(4) Uani 1 1 d . . . . .
F10 F 0.04065(19) 0.83992(11) 0.41008(11) 0.0294(4) Uani 1 1 d . . . . .
C1 C -0.1528(3) 0.58324(17) 0.32937(17) 0.0155(5) Uani 1 1 d . . . . .
C2 C -0.1833(3) 0.52104(18) 0.27048(17) 0.0176(5) Uani 1 1 d . . . . .
H1 H -0.232264 0.546883 0.214903 0.021 Uiso 1 1 calc R U . . .
C3 C -0.1428(3) 0.41778(18) 0.29129(17) 0.0168(5) Uani 1 1 d . . . . .
C4 C -0.0786(3) 0.37954(18) 0.37488(17) 0.0160(5) Uani 1 1 d . . . . .
H2 H -0.057956 0.312386 0.390236 0.019 Uiso 1 1 calc R U . . .
C5 C -0.0429(3) 0.44022(17) 0.43876(17) 0.0154(5) Uani 1 1 d . . . . .
C6 C -0.0299(3) 0.60073(17) 0.47824(17) 0.0159(5) Uani 1 1 d . . . . .
H3 H -0.048059 0.668026 0.464001 0.019 Uiso 1 1 calc R U . . .
C7 C -0.0766(3) 0.54411(17) 0.41573(17) 0.0163(5) Uani 1 1 d . . . . .
C8 C -0.2010(3) 0.69026(18) 0.30140(18) 0.0184(6) Uani 1 1 d . . . . .
C9 C -0.1642(3) 0.72936(19) 0.21123(19) 0.0232(6) Uani 1 1 d . . . . .
H4 H -0.102321 0.689409 0.170462 0.028 Uiso 1 1 calc R U . . .
C10 C -0.2184(4) 0.8273(2) 0.1809(2) 0.0274(7) Uani 1 1 d . . . . .
C11 C -0.3080(4) 0.88622(19) 0.2423(2) 0.0297(7) Uani 1 1 d . . . . .
H8 H -0.343983 0.951683 0.222318 0.036 Uiso 1 1 calc R U . . .
C12 C -0.3461(3) 0.85030(19) 0.3332(2) 0.0259(6) Uani 1 1 d . . . . .
C13 C -0.2922(3) 0.75189(18) 0.36223(19) 0.0210(6) Uani 1 1 d . . . . .
H12 H -0.317021 0.726838 0.422831 0.025 Uiso 1 1 calc R U . . .
C14 C -0.1806(5) 0.8679(2) 0.0815(2) 0.0429(8) Uani 1 1 d . . . . .
H5A H -0.117592 0.817080 0.048919 0.051 Uiso 1 1 calc R U . . .
H6B H -0.285189 0.893214 0.052171 0.051 Uiso 1 1 calc R U . . .
H7C H -0.115217 0.919091 0.080502 0.051 Uiso 1 1 calc R U . . .
C15 C -0.4438(4) 0.9158(2) 0.3998(2) 0.0392(8) Uani 1 1 d . . . . .
H9A H -0.458087 0.878615 0.458983 0.047 Uiso 1 1 calc R U . . .
H10B H -0.382395 0.967148 0.406135 0.047 Uiso 1 1 calc R U . . .
H11C H -0.553014 0.943182 0.376632 0.047 Uiso 1 1 calc R U . . .
C16 C -0.1708(3) 0.35470(17) 0.22226(17) 0.0175(5) Uani 1 1 d . . . . .
C17 C -0.2377(3) 0.26927(18) 0.24504(18) 0.0201(6) Uani 1 1 d . . . . .
C18 C -0.2663(4) 0.21226(19) 0.1802(2) 0.0253(6) Uani 1 1 d . . . . .
C19 C -0.2259(4) 0.2383(2) 0.0884(2) 0.0314(7) Uani 1 1 d . . . . .
C20 C -0.1571(4) 0.3213(2) 0.06287(19) 0.0298(7) Uani 1 1 d . . . . .
C21 C -0.1295(3) 0.37738(18) 0.12842(18) 0.0225(6) Uani 1 1 d . . . . .
C22 C 0.3604(3) 0.52031(17) 0.32058(17) 0.0161(5) Uani 1 1 d . . . . .
C23 C 0.2935(3) 0.61242(18) 0.28303(18) 0.0189(6) Uani 1 1 d . . . . .
H13 H 0.250091 0.621213 0.224664 0.023 Uiso 1 1 calc R U . . .
C24 C 0.2886(3) 0.69542(17) 0.33082(18) 0.0177(5) Uani 1 1 d . . . . .
C25 C 0.3422(3) 0.68346(17) 0.41768(18) 0.0180(6) Uani 1 1 d . . . . .
H14 H 0.329841 0.736936 0.450333 0.022 Uiso 1 1 calc R U . . .
C26 C 0.4173(3) 0.59040(17) 0.46013(17) 0.0162(5) Uani 1 1 d . . . . .
C27 C 0.4828(3) 0.58038(17) 0.54740(17) 0.0169(5) Uani 1 1 d . . . . .
H15 H 0.468684 0.634819 0.578824 0.020 Uiso 1 1 calc R U . . .
C28 C 0.4316(3) 0.50732(17) 0.41037(17) 0.0151(5) Uani 1 1 d . . . . .
C29 C 0.3515(3) 0.43710(18) 0.26797(17) 0.0182(5) Uani 1 1 d . . . . .
C30 C 0.3125(3) 0.34864(18) 0.31288(18) 0.0190(6) Uani 1 1 d . . . . .
H16 H 0.297344 0.340675 0.376965 0.023 Uiso 1 1 calc R U . . .
C31 C 0.2959(3) 0.27254(18) 0.26424(19) 0.0218(6) Uani 1 1 d . . . . .
C32 C 0.3166(3) 0.28597(19) 0.16835(19) 0.0249(6) Uani 1 1 d . . . . .
H20 H 0.305427 0.235594 0.135143 0.030 Uiso 1 1 calc R U . . .
C33 C 0.3536(3) 0.37264(19) 0.12092(19) 0.0232(6) Uani 1 1 d . . . . .
C34 C 0.3736(3) 0.44675(18) 0.17178(18) 0.0207(6) Uani 1 1 d . . . . .
H24 H 0.402478 0.504172 0.140757 0.025 Uiso 1 1 calc R U . . .
C35 C 0.2549(4) 0.17850(19) 0.3151(2) 0.0323(7) Uani 1 1 d . . . . .
H17A H 0.248011 0.134061 0.271570 0.039 Uiso 1 1 calc R U . . .
H18B H 0.342399 0.150603 0.356880 0.039 Uiso 1 1 calc R U . . .
H19C H 0.148275 0.190894 0.349439 0.039 Uiso 1 1 calc R U . . .
C36 C 0.3723(4) 0.3858(2) 0.01694(19) 0.0334(7) Uani 1 1 d . . . . .
H21A H 0.397625 0.449519 -0.004169 0.040 Uiso 1 1 calc R U . . .
H22B H 0.462734 0.337648 -0.003243 0.040 Uiso 1 1 calc R U . . .
H23C H 0.268408 0.378570 -0.008059 0.040 Uiso 1 1 calc R U . . .
C37 C 0.2281(3) 0.79535(18) 0.28415(18) 0.0210(6) Uani 1 1 d . . . . .
C38 C 0.2980(3) 0.82700(19) 0.19789(18) 0.0227(6) Uani 1 1 d . . . . .
C39 C 0.2547(4) 0.9209(2) 0.15590(19) 0.0281(7) Uani 1 1 d . . . . .
C40 C 0.1352(4) 0.98552(19) 0.1980(2) 0.0293(7) Uani 1 1 d . . . . .
C41 C 0.0634(3) 0.95725(19) 0.2834(2) 0.0261(6) Uani 1 1 d . . . . .
C42 C 0.1120(3) 0.86406(18) 0.32565(19) 0.0226(6) Uani 1 1 d . . . . .


#==============================================================================
# MOLECULAR GEOMETRY
_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C17 1.350(3) . ?
F2 C18 1.343(3) . ?
F3 C19 1.339(3) . ?
F4 C20 1.351(3) . ?
F5 C21 1.348(3) . ?
F6 C38 1.343(3) . ?
F7 C39 1.345(3) . ?
F8 C40 1.345(3) . ?
F9 C41 1.344(3) . ?
F10 C42 1.349(3) . ?
C1 C2 1.367(3) . ?
C1 C7 1.443(3) . ?
C1 C8 1.497(3) . ?
C2 H1 0.9300 . ?
C2 C3 1.429(3) . ?
C3 C4 1.367(3) . ?
C3 C16 1.481(3) . ?
C4 H2 0.9300 . ?
C4 C5 1.420(3) . ?
C5 C6 1.395(4) 2_566 ?
C5 C7 1.438(3) . ?
C6 H3 0.9300 . ?
C6 C7 1.398(3) . ?
C8 C9 1.391(4) . ?
C8 C13 1.401(3) . ?
C9 H4 0.9300 . ?
C9 C10 1.394(4) . ?
C10 C11 1.379(4) . ?
C10 C14 1.519(4) . ?
C11 H8 0.9300 . ?
C11 C12 1.390(4) . ?
C12 C13 1.395(4) . ?
C12 C15 1.511(4) . ?
C13 H12 0.9300 . ?
C14 H5A 0.9600 . ?
C14 H6B 0.9600 . ?
C14 H7C 0.9600 . ?
C15 H9A 0.9600 . ?
C15 H10B 0.9600 . ?
C15 H11C 0.9600 . ?
C16 C17 1.392(3) . ?
C16 C21 1.396(4) . ?
C17 C18 1.375(4) . ?
C18 C19 1.373(4) . ?
C19 C20 1.374(4) . ?
C20 C21 1.371(4) . ?
C22 C23 1.371(3) . ?
C22 C28 1.446(3) . ?
C22 C29 1.497(3) . ?
C23 H13 0.9300 . ?
C23 C24 1.431(3) . ?
C24 C25 1.350(4) . ?
C24 C37 1.495(4) . ?
C25 H14 0.9300 . ?
C25 C26 1.424(3) . ?
C26 C27 1.395(4) . ?
C26 C28 1.440(3) . ?
C27 H15 0.9300 . ?
C27 C28 1.392(3) 2_666 ?
C29 C30 1.403(3) . ?
C29 C34 1.396(3) . ?
C30 H16 0.9300 . ?
C30 C31 1.390(3) . ?
C31 C32 1.391(4) . ?
C31 C35 1.506(4) . ?
C32 H20 0.9300 . ?
C32 C33 1.389(4) . ?
C33 C34 1.395(4) . ?
C33 C36 1.506(4) . ?
C34 H24 0.9300 . ?
C35 H17A 0.9600 . ?
C35 H18B 0.9600 . ?
C35 H19C 0.9600 . ?
C36 H21A 0.9600 . ?
C36 H22B 0.9600 . ?
C36 H23C 0.9600 . ?
C37 C38 1.392(4) . ?
C37 C42 1.388(4) . ?
C38 C39 1.379(4) . ?
C39 C40 1.371(4) . ?
C40 C41 1.375(4) . ?
C41 C42 1.376(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C7 119.4(2) . . ?
C2 C1 C8 118.2(2) . . ?
C7 C1 C8 122.4(2) . . ?
C1 C2 H1 118.8 . . ?
C1 C2 C3 122.4(2) . . ?
C3 C2 H1 118.8 . . ?
C2 C3 C16 119.6(2) . . ?
C4 C3 C2 118.9(2) . . ?
C4 C3 C16 121.5(2) . . ?
C3 C4 H2 119.3 . . ?
C3 C4 C5 121.4(2) . . ?
C5 C4 H2 119.3 . . ?
C4 C5 C7 119.5(2) . . ?
C6 C5 C4 120.2(2) 2_566 . ?
C6 C5 C7 120.3(2) 2_566 . ?
C5 C6 H3 118.9 2_566 . ?
C5 C6 C7 122.3(2) 2_566 . ?
C7 C6 H3 118.9 . . ?
C5 C7 C1 118.3(2) . . ?
C6 C7 C1 124.2(2) . . ?
C6 C7 C5 117.5(2) . . ?
C9 C8 C1 119.7(2) . . ?
C9 C8 C13 118.6(2) . . ?
C13 C8 C1 121.6(2) . . ?
C8 C9 H4 119.4 . . ?
C8 C9 C10 121.2(3) . . ?
C10 C9 H4 119.4 . . ?
C9 C10 C14 120.3(3) . . ?
C11 C10 C9 118.9(3) . . ?
C11 C10 C14 120.8(3) . . ?
C10 C11 H8 119.1 . . ?
C10 C11 C12 121.7(2) . . ?
C12 C11 H8 119.1 . . ?
C11 C12 C13 118.6(3) . . ?
C11 C12 C15 121.1(3) . . ?
C13 C12 C15 120.2(3) . . ?
C8 C13 H12 119.5 . . ?
C12 C13 C8 121.0(3) . . ?
C12 C13 H12 119.5 . . ?
C10 C14 H5A 109.5 . . ?
C10 C14 H6B 109.5 . . ?
C10 C14 H7C 109.5 . . ?
H5A C14 H6B 109.5 . . ?
H5A C14 H7C 109.5 . . ?
H6B C14 H7C 109.5 . . ?
C12 C15 H9A 109.5 . . ?
C12 C15 H10B 109.5 . . ?
C12 C15 H11C 109.5 . . ?
H9A C15 H10B 109.5 . . ?
H9A C15 H11C 109.5 . . ?
H10B C15 H11C 109.5 . . ?
C17 C16 C3 123.4(2) . . ?
C17 C16 C21 115.1(2) . . ?
C21 C16 C3 121.5(2) . . ?
F1 C17 C16 120.4(2) . . ?
F1 C17 C18 116.6(2) . . ?
C18 C17 C16 122.9(2) . . ?
F2 C18 C17 120.5(3) . . ?
F2 C18 C19 119.7(2) . . ?
C19 C18 C17 119.9(3) . . ?
F3 C19 C18 120.1(3) . . ?
F3 C19 C20 120.7(3) . . ?
C18 C19 C20 119.2(2) . . ?
F4 C20 C19 119.7(2) . . ?
F4 C20 C21 120.1(3) . . ?
C21 C20 C19 120.2(3) . . ?
F5 C21 C16 119.9(2) . . ?
F5 C21 C20 117.4(2) . . ?
C20 C21 C16 122.7(3) . . ?
C23 C22 C28 118.8(2) . . ?
C23 C22 C29 118.4(2) . . ?
C28 C22 C29 122.8(2) . . ?
C22 C23 H13 119.0 . . ?
C22 C23 C24 122.1(2) . . ?
C24 C23 H13 119.0 . . ?
C23 C24 C37 120.2(2) . . ?
C25 C24 C23 119.8(2) . . ?
C25 C24 C37 119.9(2) . . ?
C24 C25 H14 119.4 . . ?
C24 C25 C26 121.1(2) . . ?
C26 C25 H14 119.4 . . ?
C25 C26 C28 119.3(2) . . ?
C27 C26 C25 120.4(2) . . ?
C27 C26 C28 120.3(2) . . ?
C26 C27 H15 118.5 . . ?
C28 C27 C26 123.1(2) 2_666 . ?
C28 C27 H15 118.5 2_666 . ?
C26 C28 C22 118.7(2) . . ?
C27 C28 C22 124.7(2) 2_666 . ?
C27 C28 C26 116.6(2) 2_666 . ?
C30 C29 C22 121.3(2) . . ?
C34 C29 C22 120.9(2) . . ?
C34 C29 C30 117.7(2) . . ?
C29 C30 H16 119.1 . . ?
C31 C30 C29 121.8(2) . . ?
C31 C30 H16 119.1 . . ?
C30 C31 C32 118.5(2) . . ?
C30 C31 C35 120.2(2) . . ?
C32 C31 C35 121.4(2) . . ?
C31 C32 H20 119.1 . . ?
C33 C32 C31 121.7(2) . . ?
C33 C32 H20 119.1 . . ?
C32 C33 C34 118.5(2) . . ?
C32 C33 C36 120.6(2) . . ?
C34 C33 C36 121.0(2) . . ?
C29 C34 H24 119.1 . . ?
C33 C34 C29 121.8(2) . . ?
C33 C34 H24 119.1 . . ?
C31 C35 H17A 109.5 . . ?
C31 C35 H18B 109.5 . . ?
C31 C35 H19C 109.5 . . ?
H17A C35 H18B 109.5 . . ?
H17A C35 H19C 109.5 . . ?
H18B C35 H19C 109.5 . . ?
C33 C36 H21A 109.5 . . ?
C33 C36 H22B 109.5 . . ?
C33 C36 H23C 109.5 . . ?
H21A C36 H22B 109.5 . . ?
H21A C36 H23C 109.5 . . ?
H22B C36 H23C 109.5 . . ?
C38 C37 C24 120.5(2) . . ?
C42 C37 C24 123.2(2) . . ?
C42 C37 C38 116.1(2) . . ?
F6 C38 C37 119.9(2) . . ?
F6 C38 C39 117.9(2) . . ?
C39 C38 C37 122.1(3) . . ?
F7 C39 C38 120.3(3) . . ?
F7 C39 C40 119.8(2) . . ?
C40 C39 C38 119.8(3) . . ?
F8 C40 C39 119.8(3) . . ?
F8 C40 C41 120.3(3) . . ?
C39 C40 C41 119.8(2) . . ?
F9 C41 C40 120.0(2) . . ?
F9 C41 C42 120.5(3) . . ?
C40 C41 C42 119.5(3) . . ?
F10 C42 C37 119.9(2) . . ?
F10 C42 C41 117.6(2) . . ?
C41 C42 C37 122.5(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
F1 C17 C18 F2 -0.2(4) . . . . ?
F1 C17 C18 C19 179.9(2) . . . . ?
F2 C18 C19 F3 0.1(4) . . . . ?
F2 C18 C19 C20 -179.8(3) . . . . ?
F3 C19 C20 F4 0.2(4) . . . . ?
F3 C19 C20 C21 180.0(3) . . . . ?
F4 C20 C21 F5 -2.4(4) . . . . ?
F4 C20 C21 C16 178.9(2) . . . . ?
F6 C38 C39 F7 -1.1(4) . . . . ?
F6 C38 C39 C40 -179.6(2) . . . . ?
F7 C39 C40 F8 3.4(4) . . . . ?
F7 C39 C40 C41 -176.3(2) . . . . ?
F8 C40 C41 F9 -0.3(4) . . . . ?
F8 C40 C41 C42 -179.9(2) . . . . ?
F9 C41 C42 F10 -0.7(4) . . . . ?
F9 C41 C42 C37 178.4(2) . . . . ?
C1 C2 C3 C4 3.2(4) . . . . ?
C1 C2 C3 C16 -176.8(2) . . . . ?
C1 C8 C9 C10 175.2(2) . . . . ?
C1 C8 C13 C12 -175.6(2) . . . . ?
C2 C1 C7 C5 -3.0(3) . . . . ?
C2 C1 C7 C6 175.7(2) . . . . ?
C2 C1 C8 C9 -43.8(3) . . . . ?
C2 C1 C8 C13 132.2(3) . . . . ?
C2 C3 C4 C5 -3.6(3) . . . . ?
C2 C3 C16 C17 -138.7(3) . . . . ?
C2 C3 C16 C21 41.9(3) . . . . ?
C3 C4 C5 C6 -177.0(2) . . . 2_566 ?
C3 C4 C5 C7 0.7(3) . . . . ?
C3 C16 C17 F1 -0.2(4) . . . . ?
C3 C16 C17 C18 178.7(2) . . . . ?
C3 C16 C21 F5 2.6(4) . . . . ?
C3 C16 C21 C20 -178.7(3) . . . . ?
C4 C3 C16 C17 41.4(4) . . . . ?
C4 C3 C16 C21 -138.1(3) . . . . ?
C4 C5 C7 C1 2.6(3) . . . . ?
C4 C5 C7 C6 -176.2(2) . . . . ?
C5 C6 C7 C1 179.7(2) 2_566 . . . ?
C5 C6 C7 C5 -1.5(4) 2_566 . . . ?
C6 C5 C7 C1 -179.7(2) 2_566 . . . ?
C6 C5 C7 C6 1.5(4) 2_566 . . . ?
C7 C1 C2 C3 0.2(3) . . . . ?
C7 C1 C8 C9 136.4(3) . . . . ?
C7 C1 C8 C13 -47.5(3) . . . . ?
C8 C1 C2 C3 -179.6(2) . . . . ?
C8 C1 C7 C5 176.7(2) . . . . ?
C8 C1 C7 C6 -4.5(4) . . . . ?
C8 C9 C10 C11 0.9(4) . . . . ?
C8 C9 C10 C14 -178.4(3) . . . . ?
C9 C8 C13 C12 0.4(4) . . . . ?
C9 C10 C11 C12 -0.3(4) . . . . ?
C10 C11 C12 C13 -0.3(4) . . . . ?
C10 C11 C12 C15 179.7(3) . . . . ?
C11 C12 C13 C8 0.2(4) . . . . ?
C13 C8 C9 C10 -1.0(4) . . . . ?
C14 C10 C11 C12 179.1(3) . . . . ?
C15 C12 C13 C8 -179.8(3) . . . . ?
C16 C3 C4 C5 176.4(2) . . . . ?
C16 C17 C18 F2 -179.2(2) . . . . ?
C16 C17 C18 C19 1.0(4) . . . . ?
C17 C16 C21 F5 -176.9(2) . . . . ?
C17 C16 C21 C20 1.8(4) . . . . ?
C17 C18 C19 F3 180.0(3) . . . . ?
C17 C18 C19 C20 0.0(4) . . . . ?
C18 C19 C20 F4 -179.9(3) . . . . ?
C18 C19 C20 C21 -0.1(4) . . . . ?
C19 C20 C21 F5 177.8(3) . . . . ?
C19 C20 C21 C16 -0.9(4) . . . . ?
C21 C16 C17 F1 179.3(2) . . . . ?
C21 C16 C17 C18 -1.8(4) . . . . ?
C22 C23 C24 C25 -3.8(4) . . . . ?
C22 C23 C24 C37 174.8(2) . . . . ?
C22 C29 C30 C31 176.8(2) . . . . ?
C22 C29 C34 C33 -175.2(2) . . . . ?
C23 C22 C28 C26 5.0(3) . . . . ?
C23 C22 C28 C27 -173.8(2) . . . 2_666 ?
C23 C22 C29 C30 -139.2(3) . . . . ?
C23 C22 C29 C34 37.6(3) . . . . ?
C23 C24 C25 C26 5.4(4) . . . . ?
C23 C24 C37 C38 -52.5(3) . . . . ?
C23 C24 C37 C42 132.9(3) . . . . ?
C24 C25 C26 C27 175.5(2) . . . . ?
C24 C25 C26 C28 -1.8(4) . . . . ?
C24 C37 C38 F6 2.5(4) . . . . ?
C24 C37 C38 C39 -175.0(2) . . . . ?
C24 C37 C42 F10 -4.0(4) . . . . ?
C24 C37 C42 C41 176.9(2) . . . . ?
C25 C24 C37 C38 126.1(3) . . . . ?
C25 C24 C37 C42 -48.5(4) . . . . ?
C25 C26 C27 C28 -175.3(2) . . . 2_666 ?
C25 C26 C28 C22 -3.4(3) . . . . ?
C25 C26 C28 C27 175.5(2) . . . 2_666 ?
C27 C26 C28 C22 179.3(2) . . . . ?
C27 C26 C28 C27 -1.8(4) . . . 2_666 ?
C28 C22 C23 C24 -1.5(4) . . . . ?
C28 C22 C29 C30 38.8(4) . . . . ?
C28 C22 C29 C34 -144.3(2) . . . . ?
C28 C26 C27 C28 2.0(4) . . . 2_666 ?
C29 C22 C23 C24 176.6(2) . . . . ?
C29 C22 C28 C26 -173.1(2) . . . . ?
C29 C22 C28 C27 8.1(4) . . . 2_666 ?
C29 C30 C31 C32 -0.9(4) . . . . ?
C29 C30 C31 C35 179.6(2) . . . . ?
C30 C29 C34 C33 1.7(4) . . . . ?
C30 C31 C32 C33 0.2(4) . . . . ?
C31 C32 C33 C34 1.4(4) . . . . ?
C31 C32 C33 C36 -178.9(3) . . . . ?
C32 C33 C34 C29 -2.3(4) . . . . ?
C34 C29 C30 C31 -0.1(4) . . . . ?
C35 C31 C32 C33 179.7(3) . . . . ?
C36 C33 C34 C29 177.9(3) . . . . ?
C37 C24 C25 C26 -173.2(2) . . . . ?
C37 C38 C39 F7 176.4(2) . . . . ?
C37 C38 C39 C40 -2.1(4) . . . . ?
C38 C37 C42 F10 -178.7(2) . . . . ?
C38 C37 C42 C41 2.2(4) . . . . ?
C38 C39 C40 F8 -178.1(2) . . . . ?
C38 C39 C40 C41 2.2(4) . . . . ?
C39 C40 C41 F9 179.3(2) . . . . ?
C39 C40 C41 C42 -0.2(4) . . . . ?
C40 C41 C42 F10 178.8(2) . . . . ?
C40 C41 C42 C37 -2.1(4) . . . . ?
C42 C37 C38 F6 177.4(2) . . . . ?
C42 C37 C38 C39 -0.1(4) . . . . ?

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.
####################################################################### 
# 
# 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_stu1038
_database_code_depnum_ccdc_archive 'CCDC 2234488'
loop_
_audit_author_name
_audit_author_address
'Ryota Sato'
;University of Tsukuba
Japan
;
_audit_update_record             
;
2023-01-05 deposited with the CCDC.	2023-05-04 downloaded from the CCDC.
;
_chemical_formula_moiety         'C34 H4 F20'
#==============================================================================
# CHEMICAL DATA
_chemical_formula_sum            'C34 H4 F20'
_chemical_formula_weight         792.37
_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 0.0033 0.0016
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
F F 0.0171 0.0103
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,1/2+Y,1/2-Z
3 -X,-Y,-Z
4 +X,-1/2-Y,-1/2+Z

#------------------------------------------------------------------------------
_cell_length_a                   6.1719(8)
_cell_length_b                   20.881(3)
_cell_length_c                   11.0462(15)
_cell_angle_alpha                90.0000
_cell_angle_beta                 103.068(2)
_cell_angle_gamma                90.0000
_cell_volume                     1386.7(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3740
_cell_measurement_temperature    120
_cell_measurement_theta_max      27.10
_cell_measurement_theta_min      3.39
_exptl_absorpt_coefficient_mu    0.205
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.6893
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   
;
SADABS V2008/1 (Bruker AXS) 
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.898
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
#------------------------------------------------------------------------------
_exptl_crystal_description       nONE
_exptl_crystal_F_000             776.00
_exptl_crystal_size_max          0.402
_exptl_crystal_size_mid          0.054
_exptl_crystal_size_min          0.042
_diffrn_reflns_av_R_equivalents  0.0175
_diffrn_reflns_av_unetI/netI     0.0206
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            7767
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.101
_diffrn_reflns_theta_min         1.951
#==============================================================================
# EXPERIMENTAL DATA
_diffrn_ambient_temperature      120
_diffrn_detector_area_resol_mean 8.333
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  'Bruker Helios multilayer confocal mirror'
_diffrn_radiation_source         'Bruker TXS fine-focus rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count .
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2539
_reflns_number_total             3044
_reflns_threshold_expression     F²>2.0σ(F²)
_computing_cell_refinement       Unknown
#==============================================================================
_computing_data_collection       Unknown
_computing_data_reduction        Unknown
_computing_molecular_graphics    'CrystalStructure 4.3'
_computing_publication_material  'CrystalStructure 4.3 (Rigaku, 2019)'
_computing_structure_refinement  'SHELXL Version 2018/3 (Sheldrick, 2008)'
_computing_structure_solution    'SIR92 (Altomare, et al., 1994)'
_refine_diff_density_max         0.30
_refine_diff_density_min         -0.21
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_number_parameters     252
_refine_ls_number_reflns         3044
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0396
_refine_ls_R_factor_gt           0.0317
_refine_ls_shift/su_max          0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0449P)²+0.6207P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0831
_refine_ls_wR_factor_ref         0.0883
#==============================================================================
# REFINEMENT DATA
_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.42834(15) 0.39284(4) 0.77471(8) 0.0275(2) Uani 1 1 d . . . . .
F2 F 0.6688(2) 0.32275(5) 0.96361(9) 0.0412(3) Uani 1 1 d . . . . .
F3 F 1.10040(19) 0.35330(5) 1.06083(9) 0.0435(3) Uani 1 1 d . . . . .
F4 F 1.28769(15) 0.45575(5) 0.97212(9) 0.0343(3) Uani 1 1 d . . . . .
F5 F 1.04396(15) 0.52711(5) 0.78703(8) 0.0288(2) Uani 1 1 d . . . . .
F6 F -0.12458(14) 0.61114(4) 0.49862(8) 0.0272(2) Uani 1 1 d . . . . .
F7 F -0.35306(15) 0.71104(5) 0.55531(9) 0.0330(2) Uani 1 1 d . . . . .
F8 F -0.15496(18) 0.79645(5) 0.73254(10) 0.0370(3) Uani 1 1 d . . . . .
F9 F 0.27936(17) 0.78288(4) 0.84540(9) 0.0320(2) Uani 1 1 d . . . . .
F10 F 0.51621(14) 0.68483(4) 0.78667(8) 0.0244(2) Uani 1 1 d . . . . .
C1 C 0.5893(2) 0.50079(6) 0.67353(12) 0.0142(3) Uani 1 1 d . . . . .
C2 C 0.4756(2) 0.55279(7) 0.70222(12) 0.0157(3) Uani 1 1 d . . . . .
C3 C 0.3346(2) 0.58894(6) 0.60734(12) 0.0155(3) Uani 1 1 d . . . . .
C4 C 0.3144(2) 0.57166(6) 0.48489(12) 0.0148(3) Uani 1 1 d . . . . .
C5 C 0.4299(2) 0.51826(6) 0.45271(12) 0.0138(3) Uani 1 1 d . . . . .
C6 C 0.7286(2) 0.46191(6) 0.77532(12) 0.0145(3) Uani 1 1 d . . . . .
C7 C 0.6393(2) 0.40922(7) 0.82288(13) 0.0184(3) Uani 1 1 d . . . . .
C8 C 0.7614(3) 0.37275(7) 0.91888(14) 0.0248(3) Uani 1 1 d . . . . .
C9 C 0.9801(3) 0.38839(8) 0.96828(13) 0.0263(3) Uani 1 1 d . . . . .
C10 C 1.0754(2) 0.43998(8) 0.92265(13) 0.0231(3) Uani 1 1 d . . . . .
C11 C 0.9489(2) 0.47609(7) 0.82748(13) 0.0185(3) Uani 1 1 d . . . . .
C12 C 0.2062(2) 0.64387(7) 0.63989(12) 0.0161(3) Uani 1 1 d . . . . .
C13 C -0.0176(2) 0.65313(7) 0.58346(13) 0.0190(3) Uani 1 1 d . . . . .
C14 C -0.1394(3) 0.70392(7) 0.61255(14) 0.0230(3) Uani 1 1 d . . . . .
C15 C -0.0388(3) 0.74723(7) 0.70226(14) 0.0237(3) Uani 1 1 d . . . . .
C16 C 0.1810(3) 0.74001(7) 0.76028(13) 0.0219(3) Uani 1 1 d . . . . .
C17 C 0.3009(2) 0.68915(7) 0.72887(13) 0.0182(3) Uani 1 1 d . . . . .
H1 H 0.488(3) 0.5637(8) 0.7872(15) 0.016(4) Uiso 1 1 d . . . . .
H2 H 0.224(3) 0.5964(8) 0.4206(15) 0.016(4) Uiso 1 1 d . . . . .


#==============================================================================
# MOLECULAR GEOMETRY
_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C7 1.3349(17) . ?
F2 C8 1.3371(18) . ?
F3 C9 1.3378(16) . ?
F4 C10 1.3414(17) . ?
F5 C11 1.3405(17) . ?
F6 C13 1.3428(16) . ?
F7 C14 1.3357(18) . ?
F8 C15 1.3379(17) . ?
F9 C16 1.3402(17) . ?
F10 C17 1.3409(17) . ?
C1 C2 1.3681(19) . ?
C1 C5 1.4290(18) 3_666 ?
C1 C6 1.4918(18) . ?
C2 C3 1.4189(19) . ?
C2 H1 0.951(16) . ?
C3 C4 1.3780(19) . ?
C3 C12 1.4839(19) . ?
C4 C5 1.4118(19) . ?
C4 H2 0.950(17) . ?
C5 C5 1.419(3) 3_666 ?
C6 C7 1.3859(19) . ?
C6 C11 1.384(2) . ?
C7 C8 1.382(2) . ?
C8 C9 1.376(2) . ?
C9 C10 1.376(2) . ?
C10 C11 1.383(2) . ?
C12 C13 1.394(2) . ?
C12 C17 1.3936(19) . ?
C13 C14 1.379(2) . ?
C14 C15 1.381(2) . ?
C15 C16 1.371(2) . ?
C16 C17 1.383(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C5 120.88(12) . 3_666 ?
C2 C1 C6 119.70(12) . . ?
C5 C1 C6 119.38(12) 3_666 . ?
C1 C2 C3 120.80(12) . . ?
C1 C2 H1 119.1(10) . . ?
C3 C2 H1 120.1(10) . . ?
C2 C3 C12 120.29(12) . . ?
C4 C3 C2 119.35(12) . . ?
C4 C3 C12 120.35(12) . . ?
C3 C4 C5 121.00(12) . . ?
C3 C4 H2 120.0(10) . . ?
C5 C4 H2 119.0(10) . . ?
C4 C5 C1 122.04(12) . 3_666 ?
C4 C5 C5 119.85(15) . 3_666 ?
C5 C5 C1 118.11(15) 3_666 3_666 ?
C7 C6 C1 120.46(12) . . ?
C11 C6 C1 122.82(12) . . ?
C11 C6 C7 116.72(12) . . ?
F1 C7 C6 119.20(12) . . ?
F1 C7 C8 118.55(13) . . ?
C8 C7 C6 122.25(14) . . ?
F2 C8 C7 120.62(15) . . ?
F2 C8 C9 120.09(14) . . ?
C9 C8 C7 119.28(14) . . ?
F3 C9 C8 119.87(15) . . ?
F3 C9 C10 119.96(15) . . ?
C10 C9 C8 120.17(13) . . ?
F4 C10 C9 120.11(13) . . ?
F4 C10 C11 120.49(14) . . ?
C9 C10 C11 119.38(14) . . ?
F5 C11 C6 119.62(12) . . ?
F5 C11 C10 118.19(13) . . ?
C10 C11 C6 122.18(14) . . ?
C13 C12 C3 121.89(12) . . ?
C17 C12 C3 122.23(12) . . ?
C17 C12 C13 115.88(13) . . ?
F6 C13 C12 120.16(13) . . ?
F6 C13 C14 117.18(13) . . ?
C14 C13 C12 122.64(13) . . ?
F7 C14 C13 120.47(14) . . ?
F7 C14 C15 120.15(13) . . ?
C13 C14 C15 119.38(14) . . ?
F8 C15 C14 120.21(14) . . ?
F8 C15 C16 119.80(14) . . ?
C16 C15 C14 119.99(13) . . ?
F9 C16 C15 119.85(13) . . ?
F9 C16 C17 120.38(14) . . ?
C15 C16 C17 119.76(14) . . ?
F10 C17 C12 120.19(12) . . ?
F10 C17 C16 117.46(13) . . ?
C16 C17 C12 122.34(13) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
F1 C7 C8 F2 -1.0(2) . . . . ?
F1 C7 C8 C9 178.99(13) . . . . ?
F2 C8 C9 F3 0.3(2) . . . . ?
F2 C8 C9 C10 -179.76(14) . . . . ?
F3 C9 C10 F4 -1.0(2) . . . . ?
F3 C9 C10 C11 -179.61(13) . . . . ?
F4 C10 C11 F5 -0.3(2) . . . . ?
F4 C10 C11 C6 -179.03(13) . . . . ?
F6 C13 C14 F7 -1.7(2) . . . . ?
F6 C13 C14 C15 177.85(13) . . . . ?
F7 C14 C15 F8 0.2(2) . . . . ?
F7 C14 C15 C16 -179.58(14) . . . . ?
F8 C15 C16 F9 -1.2(2) . . . . ?
F8 C15 C16 C17 -179.97(14) . . . . ?
F9 C16 C17 F10 0.1(2) . . . . ?
F9 C16 C17 C12 -179.24(13) . . . . ?
C1 C2 C3 C4 -0.7(2) . . . . ?
C1 C2 C3 C12 177.86(13) . . . . ?
C1 C6 C7 F1 1.4(2) . . . . ?
C1 C6 C7 C8 -178.63(13) . . . . ?
C1 C6 C11 F5 0.7(2) . . . . ?
C1 C6 C11 C10 179.36(13) . . . . ?
C2 C1 C6 C7 91.72(16) . . . . ?
C2 C1 C6 C11 -87.81(17) . . . . ?
C2 C3 C4 C5 0.6(2) . . . . ?
C2 C3 C12 C13 -134.93(14) . . . . ?
C2 C3 C12 C17 44.8(2) . . . . ?
C3 C4 C5 C1 179.66(13) . . . 3_666 ?
C3 C4 C5 C5 -0.3(2) . . . 3_666 ?
C3 C12 C13 F6 1.3(2) . . . . ?
C3 C12 C13 C14 -179.96(13) . . . . ?
C3 C12 C17 F10 1.4(2) . . . . ?
C3 C12 C17 C16 -179.32(13) . . . . ?
C4 C3 C12 C13 43.6(2) . . . . ?
C4 C3 C12 C17 -136.66(14) . . . . ?
C5 C1 C2 C3 0.4(2) 3_666 . . . ?
C5 C1 C6 C7 -86.02(17) 3_666 . . . ?
C5 C1 C6 C11 94.45(16) 3_666 . . . ?
C6 C1 C2 C3 -177.31(12) . . . . ?
C6 C7 C8 F2 179.05(13) . . . . ?
C6 C7 C8 C9 -1.0(2) . . . . ?
C7 C6 C11 F5 -178.87(12) . . . . ?
C7 C6 C11 C10 -0.2(2) . . . . ?
C7 C8 C9 F3 -179.69(14) . . . . ?
C7 C8 C9 C10 0.3(2) . . . . ?
C8 C9 C10 F4 179.00(14) . . . . ?
C8 C9 C10 C11 0.4(2) . . . . ?
C9 C10 C11 F5 178.22(13) . . . . ?
C9 C10 C11 C6 -0.5(2) . . . . ?
C11 C6 C7 F1 -179.04(12) . . . . ?
C11 C6 C7 C8 0.9(2) . . . . ?
C12 C3 C4 C5 -177.93(13) . . . . ?
C12 C13 C14 F7 179.52(13) . . . . ?
C12 C13 C14 C15 -1.0(2) . . . . ?
C13 C12 C17 F10 -178.88(12) . . . . ?
C13 C12 C17 C16 0.4(2) . . . . ?
C13 C14 C15 F8 -179.35(14) . . . . ?
C13 C14 C15 C16 0.9(2) . . . . ?
C14 C15 C16 F9 178.58(14) . . . . ?
C14 C15 C16 C17 -0.2(2) . . . . ?
C15 C16 C17 F10 178.85(13) . . . . ?
C15 C16 C17 C12 -0.5(2) . . . . ?
C17 C12 C13 F6 -178.47(12) . . . . ?
C17 C12 C13 C14 0.3(2) . . . . ?

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.
####################################################################### 
# 
# 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_stu1101
_database_code_depnum_ccdc_archive 'CCDC 2234491'
loop_
_audit_author_name
_audit_author_address
'Ryota Sato'
;University of Tsukuba
Japan
;
_audit_update_record             
;
2023-01-05 deposited with the CCDC.	2023-05-04 downloaded from the CCDC.
;
_chemical_formula_moiety         'C27 H20 F5 N'
#==============================================================================
# CHEMICAL DATA
_chemical_formula_sum            'C27 H20 F5 N'
_chemical_formula_weight         453.45
_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 0.0033 0.0016
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
N N 0.0061 0.0033
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
F F 0.0171 0.0103
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,-Y,-Z

#------------------------------------------------------------------------------
_cell_length_a                   8.4077(13)
_cell_length_b                   11.5245(18)
_cell_length_c                   11.9243(19)
_cell_angle_alpha                73.192(2)
_cell_angle_beta                 81.887(2)
_cell_angle_gamma                85.161(2)
_cell_volume                     1093.8(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2811
_cell_measurement_temperature    120
_cell_measurement_theta_max      26.92
_cell_measurement_theta_min      2.86
_exptl_absorpt_coefficient_mu    0.110
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.6942
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   
;
SADABS V2008/1 (Bruker AXS) 
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.377
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
#------------------------------------------------------------------------------
_exptl_crystal_description       nONE
_exptl_crystal_F_000             468.00
_exptl_crystal_size_max          0.647
_exptl_crystal_size_mid          0.040
_exptl_crystal_size_min          0.030
_diffrn_reflns_av_R_equivalents  0.0331
_diffrn_reflns_av_unetI/netI     0.0433
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            12629
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.104
_diffrn_reflns_theta_min         1.798
_diffrn_ambient_temperature      120
_diffrn_detector_area_resol_mean 8.333
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  'Bruker Helios multilayer confocal mirror'
_diffrn_radiation_source         'Bruker TXS fine-focus rotating anode'
#==============================================================================
# EXPERIMENTAL DATA
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count .
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3443
_reflns_number_total             4789
_reflns_threshold_expression     F²>2.0σ(F²)
_computing_cell_refinement       Unknown
#==============================================================================
_computing_data_collection       Unknown
_computing_data_reduction        Unknown
_computing_molecular_graphics    'CrystalStructure 4.3'
_computing_publication_material  'CrystalStructure 4.3 (Rigaku, 2019)'
_computing_structure_refinement  'SHELXL Version 2018/3 (Sheldrick, 2008)'
_computing_structure_solution    'SIR92 (Altomare, et al., 1994)'
_refine_diff_density_max         0.41
_refine_diff_density_min         -0.46
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     298
_refine_ls_number_reflns         4789
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0781
_refine_ls_R_factor_gt           0.0546
_refine_ls_shift/su_max          0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0673P)²+0.7926P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1391
_refine_ls_wR_factor_ref         0.1545
#==============================================================================
# REFINEMENT DATA
_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.38866(19) -0.03161(12) 0.12424(12) 0.0353(4) Uani 1 1 d . . . . .
F2 F 0.3646(2) -0.18125(15) -0.00782(13) 0.0441(4) Uani 1 1 d . . . . .
F3 F 0.3460(2) -0.42345(14) 0.09395(14) 0.0437(4) Uani 1 1 d . . . . .
F4 F 0.35237(19) -0.51540(12) 0.33076(14) 0.0409(4) Uani 1 1 d . . . . .
F5 F 0.36856(19) -0.36752(12) 0.46486(12) 0.0343(4) Uani 1 1 d . . . . .
N1 N 0.2044(2) 0.17235(16) 0.43046(15) 0.0203(4) Uani 1 1 d . . . . .
C1 C 0.3158(3) 0.07197(18) 0.42962(18) 0.0188(4) Uani 1 1 d . . . . .
C2 C 0.2951(3) -0.00664(19) 0.36577(18) 0.0202(5) Uani 1 1 d . . . . .
H1 H 0.212327 0.008759 0.318566 0.024 Uiso 1 1 calc R U . . .
C3 C 0.3990(3) -0.11061(18) 0.37149(18) 0.0192(4) Uani 1 1 d . . . . .
C4 C 0.4798(3) 0.13534(19) 0.55813(18) 0.0198(4) Uani 1 1 d . . . . .
H2 H 0.417105 0.206945 0.550865 0.024 Uiso 1 1 calc R U . . .
C5 C 0.4490(3) 0.05333(18) 0.49638(18) 0.0183(4) Uani 1 1 d . . . . .
C6 C 0.1250(3) 0.22795(18) 0.32920(18) 0.0191(4) Uani 1 1 d . . . . .
C7 C -0.0412(3) 0.24550(18) 0.33868(19) 0.0200(4) Uani 1 1 d . . . . .
H3 H -0.101753 0.221644 0.412406 0.024 Uiso 1 1 calc R U . . .
C8 C -0.1186(3) 0.29877(19) 0.23833(19) 0.0222(5) Uani 1 1 d . . . . .
C9 C -0.0258(3) 0.33345(19) 0.12889(19) 0.0232(5) Uani 1 1 d . . . . .
H4 H -0.076212 0.368746 0.061736 0.028 Uiso 1 1 calc R U . . .
C10 C 0.1419(3) 0.31635(18) 0.11767(19) 0.0221(5) Uani 1 1 d . . . . .
C11 C 0.2157(3) 0.26456(19) 0.21879(19) 0.0210(5) Uani 1 1 d . . . . .
H5 H 0.327164 0.254143 0.212764 0.025 Uiso 1 1 calc R U . . .
C12 C -0.2994(3) 0.3132(2) 0.2486(2) 0.0325(6) Uani 1 1 d . . . . .
H6A H -0.343274 0.284819 0.330055 0.039 Uiso 1 1 calc R U . . .
H7B H -0.330966 0.397285 0.218019 0.039 Uiso 1 1 calc R U . . .
H8C H -0.339247 0.266752 0.204315 0.039 Uiso 1 1 calc R U . . .
C13 C 0.2408(3) 0.3501(2) -0.0013(2) 0.0293(5) Uani 1 1 d . . . . .
H9A H 0.171379 0.384513 -0.061178 0.035 Uiso 1 1 calc R U . . .
H10B H 0.316774 0.408408 -0.003021 0.035 Uiso 1 1 calc R U . . .
H11C H 0.297264 0.278906 -0.015815 0.035 Uiso 1 1 calc R U . . .
C14 C 0.1353(3) 0.18534(19) 0.54252(18) 0.0191(4) Uani 1 1 d . . . . .
C15 C 0.1024(3) 0.0839(2) 0.63724(19) 0.0211(5) Uani 1 1 d . . . . .
H12 H 0.112559 0.007304 0.625143 0.025 Uiso 1 1 calc R U . . .
C16 C 0.0544(3) 0.0954(2) 0.75022(19) 0.0233(5) Uani 1 1 d . . . . .
C17 C 0.0385(3) 0.2105(2) 0.7663(2) 0.0245(5) Uani 1 1 d . . . . .
H13 H 0.007939 0.218817 0.841789 0.029 Uiso 1 1 calc R U . . .
C18 C 0.0674(3) 0.3140(2) 0.6719(2) 0.0233(5) Uani 1 1 d . . . . .
C19 C 0.1143(3) 0.30050(19) 0.55990(19) 0.0222(5) Uani 1 1 d . . . . .
H14 H 0.131755 0.368830 0.495860 0.027 Uiso 1 1 calc R U . . .
C20 C 0.0239(3) -0.0164(2) 0.8521(2) 0.0346(6) Uani 1 1 d . . . . .
H15A H 0.040785 -0.087058 0.823834 0.042 Uiso 1 1 calc R U . . .
H16B H 0.096407 -0.021355 0.908862 0.042 Uiso 1 1 calc R U . . .
H17C H -0.084978 -0.012281 0.888590 0.042 Uiso 1 1 calc R U . . .
C21 C 0.0598(3) 0.4382(2) 0.6916(2) 0.0319(6) Uani 1 1 d . . . . .
H18A H 0.025511 0.431549 0.773414 0.038 Uiso 1 1 calc R U . . .
H19B H 0.164393 0.471356 0.669721 0.038 Uiso 1 1 calc R U . . .
H20C H -0.015267 0.490571 0.644209 0.038 Uiso 1 1 calc R U . . .
C22 C 0.3794(3) -0.19357(19) 0.29980(19) 0.0209(5) Uani 1 1 d . . . . .
C23 C 0.3768(3) -0.1504(2) 0.1784(2) 0.0249(5) Uani 1 1 d . . . . .
C24 C 0.3660(3) -0.2267(2) 0.1094(2) 0.0305(6) Uani 1 1 d . . . . .
C25 C 0.3581(3) -0.3494(2) 0.1606(2) 0.0300(6) Uani 1 1 d . . . . .
C26 C 0.3608(3) -0.3959(2) 0.2802(2) 0.0284(5) Uani 1 1 d . . . . .
C27 C 0.3703(3) -0.3181(2) 0.3480(2) 0.0245(5) Uani 1 1 d . . . . .


#==============================================================================
# MOLECULAR GEOMETRY
_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C23 1.340(3) . ?
F2 C24 1.345(3) . ?
F3 C25 1.342(2) . ?
F4 C26 1.338(3) . ?
F5 C27 1.342(3) . ?
N1 C1 1.427(3) . ?
N1 C6 1.422(3) . ?
N1 C14 1.424(3) . ?
C1 C2 1.376(3) . ?
C1 C5 1.431(3) . ?
C2 H1 0.9300 . ?
C2 C3 1.413(3) . ?
C3 C4 1.370(3) 2_656 ?
C3 C22 1.487(3) . ?
C4 H2 0.9300 . ?
C4 C5 1.414(3) . ?
C5 C5 1.427(4) 2_656 ?
C6 C7 1.389(3) . ?
C6 C11 1.394(3) . ?
C7 H3 0.9300 . ?
C7 C8 1.400(3) . ?
C8 C9 1.391(3) . ?
C8 C12 1.507(3) . ?
C9 H4 0.9300 . ?
C9 C10 1.400(3) . ?
C10 C11 1.388(3) . ?
C10 C13 1.503(3) . ?
C11 H5 0.9300 . ?
C12 H6A 0.9600 . ?
C12 H7B 0.9600 . ?
C12 H8C 0.9600 . ?
C13 H9A 0.9600 . ?
C13 H10B 0.9600 . ?
C13 H11C 0.9600 . ?
C14 C15 1.386(3) . ?
C14 C19 1.395(3) . ?
C15 H12 0.9300 . ?
C15 C16 1.392(3) . ?
C16 C17 1.387(3) . ?
C16 C20 1.505(3) . ?
C17 H13 0.9300 . ?
C17 C18 1.394(3) . ?
C18 C19 1.388(3) . ?
C18 C21 1.511(3) . ?
C19 H14 0.9300 . ?
C20 H15A 0.9600 . ?
C20 H16B 0.9600 . ?
C20 H17C 0.9600 . ?
C21 H18A 0.9600 . ?
C21 H19B 0.9600 . ?
C21 H20C 0.9600 . ?
C22 C23 1.390(3) . ?
C22 C27 1.388(3) . ?
C23 C24 1.382(3) . ?
C24 C25 1.372(4) . ?
C25 C26 1.373(4) . ?
C26 C27 1.383(3) . ?

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 N1 C1 119.36(17) . . ?
C6 N1 C14 119.64(17) . . ?
C14 N1 C1 117.30(17) . . ?
N1 C1 C5 119.36(18) . . ?
C2 C1 N1 120.47(19) . . ?
C2 C1 C5 120.17(19) . . ?
C1 C2 H1 119.8 . . ?
C1 C2 C3 120.4(2) . . ?
C3 C2 H1 119.8 . . ?
C2 C3 C22 120.32(19) . . ?
C4 C3 C2 120.46(19) 2_656 . ?
C4 C3 C22 119.22(19) 2_656 . ?
C3 C4 H2 119.6 2_656 . ?
C3 C4 C5 120.83(19) 2_656 . ?
C5 C4 H2 119.6 . . ?
C4 C5 C1 122.11(18) . . ?
C4 C5 C5 119.1(2) . 2_656 ?
C5 C5 C1 118.8(2) 2_656 . ?
C7 C6 N1 121.00(19) . . ?
C7 C6 C11 119.65(19) . . ?
C11 C6 N1 119.35(19) . . ?
C6 C7 H3 119.7 . . ?
C6 C7 C8 120.6(2) . . ?
C8 C7 H3 119.7 . . ?
C7 C8 C12 120.4(2) . . ?
C9 C8 C7 118.7(2) . . ?
C9 C8 C12 120.9(2) . . ?
C8 C9 H4 119.3 . . ?
C8 C9 C10 121.4(2) . . ?
C10 C9 H4 119.3 . . ?
C9 C10 C13 121.1(2) . . ?
C11 C10 C9 118.7(2) . . ?
C11 C10 C13 120.3(2) . . ?
C6 C11 H5 119.6 . . ?
C10 C11 C6 120.9(2) . . ?
C10 C11 H5 119.6 . . ?
C8 C12 H6A 109.5 . . ?
C8 C12 H7B 109.5 . . ?
C8 C12 H8C 109.5 . . ?
H6A C12 H7B 109.5 . . ?
H6A C12 H8C 109.5 . . ?
H7B C12 H8C 109.5 . . ?
C10 C13 H9A 109.5 . . ?
C10 C13 H10B 109.5 . . ?
C10 C13 H11C 109.5 . . ?
H9A C13 H10B 109.5 . . ?
H9A C13 H11C 109.5 . . ?
H10B C13 H11C 109.5 . . ?
C15 C14 N1 120.48(18) . . ?
C15 C14 C19 119.60(19) . . ?
C19 C14 N1 119.66(19) . . ?
C14 C15 H12 119.6 . . ?
C14 C15 C16 120.7(2) . . ?
C16 C15 H12 119.6 . . ?
C15 C16 C20 119.7(2) . . ?
C17 C16 C15 118.8(2) . . ?
C17 C16 C20 121.5(2) . . ?
C16 C17 H13 119.3 . . ?
C16 C17 C18 121.4(2) . . ?
C18 C17 H13 119.3 . . ?
C17 C18 C21 121.0(2) . . ?
C19 C18 C17 118.8(2) . . ?
C19 C18 C21 120.1(2) . . ?
C14 C19 H14 119.7 . . ?
C18 C19 C14 120.5(2) . . ?
C18 C19 H14 119.7 . . ?
C16 C20 H15A 109.5 . . ?
C16 C20 H16B 109.5 . . ?
C16 C20 H17C 109.5 . . ?
H15A C20 H16B 109.5 . . ?
H15A C20 H17C 109.5 . . ?
H16B C20 H17C 109.5 . . ?
C18 C21 H18A 109.5 . . ?
C18 C21 H19B 109.5 . . ?
C18 C21 H20C 109.5 . . ?
H18A C21 H19B 109.5 . . ?
H18A C21 H20C 109.5 . . ?
H19B C21 H20C 109.5 . . ?
C23 C22 C3 121.3(2) . . ?
C27 C22 C3 122.6(2) . . ?
C27 C22 C23 116.1(2) . . ?
F1 C23 C22 120.00(19) . . ?
F1 C23 C24 117.8(2) . . ?
C24 C23 C22 122.2(2) . . ?
F2 C24 C23 120.3(2) . . ?
F2 C24 C25 119.8(2) . . ?
C25 C24 C23 119.9(2) . . ?
F3 C25 C24 120.0(2) . . ?
F3 C25 C26 120.2(2) . . ?
C24 C25 C26 119.8(2) . . ?
F4 C26 C25 120.2(2) . . ?
F4 C26 C27 120.3(2) . . ?
C25 C26 C27 119.5(2) . . ?
F5 C27 C22 120.16(19) . . ?
F5 C27 C26 117.3(2) . . ?
C26 C27 C22 122.5(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
F1 C23 C24 F2 -1.2(3) . . . . ?
F1 C23 C24 C25 178.2(2) . . . . ?
F2 C24 C25 F3 -1.2(4) . . . . ?
F2 C24 C25 C26 179.5(2) . . . . ?
F3 C25 C26 F4 0.4(4) . . . . ?
F3 C25 C26 C27 -178.8(2) . . . . ?
F4 C26 C27 F5 -0.8(3) . . . . ?
F4 C26 C27 C22 179.9(2) . . . . ?
N1 C1 C2 C3 -175.62(19) . . . . ?
N1 C1 C5 C4 -3.8(3) . . . . ?
N1 C1 C5 C5 174.3(2) . . . 2_656 ?
N1 C6 C7 C8 -179.10(18) . . . . ?
N1 C6 C11 C10 178.37(18) . . . . ?
N1 C14 C15 C16 171.7(2) . . . . ?
N1 C14 C19 C18 -171.4(2) . . . . ?
C1 N1 C6 C7 128.1(2) . . . . ?
C1 N1 C6 C11 -51.5(3) . . . . ?
C1 N1 C14 C15 -34.3(3) . . . . ?
C1 N1 C14 C19 139.9(2) . . . . ?
C1 C2 C3 C4 0.9(3) . . . 2_656 ?
C1 C2 C3 C22 -178.3(2) . . . . ?
C2 C1 C5 C4 176.5(2) . . . . ?
C2 C1 C5 C5 -5.4(4) . . . 2_656 ?
C2 C3 C22 C23 53.7(3) . . . . ?
C2 C3 C22 C27 -129.3(2) . . . . ?
C3 C4 C5 C1 175.0(2) 2_656 . . . ?
C3 C4 C5 C5 -3.0(4) 2_656 . . 2_656 ?
C3 C22 C23 F1 -1.4(3) . . . . ?
C3 C22 C23 C24 177.0(2) . . . . ?
C3 C22 C27 F5 4.4(3) . . . . ?
C3 C22 C27 C26 -176.4(2) . . . . ?
C4 C3 C22 C23 -125.4(2) 2_656 . . . ?
C4 C3 C22 C27 51.5(3) 2_656 . . . ?
C5 C1 C2 C3 4.1(3) . . . . ?
C6 N1 C1 C2 -31.0(3) . . . . ?
C6 N1 C1 C5 149.3(2) . . . . ?
C6 N1 C14 C15 123.9(2) . . . . ?
C6 N1 C14 C19 -61.9(3) . . . . ?
C6 C7 C8 C9 0.2(3) . . . . ?
C6 C7 C8 C12 177.7(2) . . . . ?
C7 C6 C11 C10 -1.2(3) . . . . ?
C7 C8 C9 C10 -0.1(3) . . . . ?
C8 C9 C10 C11 -0.6(3) . . . . ?
C8 C9 C10 C13 177.9(2) . . . . ?
C9 C10 C11 C6 1.3(3) . . . . ?
C11 C6 C7 C8 0.5(3) . . . . ?
C12 C8 C9 C10 -177.6(2) . . . . ?
C13 C10 C11 C6 -177.2(2) . . . . ?
C14 N1 C1 C2 127.2(2) . . . . ?
C14 N1 C1 C5 -52.5(3) . . . . ?
C14 N1 C6 C7 -29.7(3) . . . . ?
C14 N1 C6 C11 150.7(2) . . . . ?
C14 C15 C16 C17 0.6(3) . . . . ?
C14 C15 C16 C20 -178.3(2) . . . . ?
C15 C14 C19 C18 2.8(3) . . . . ?
C15 C16 C17 C18 0.9(3) . . . . ?
C16 C17 C18 C19 -0.5(3) . . . . ?
C16 C17 C18 C21 -176.2(2) . . . . ?
C17 C18 C19 C14 -1.3(3) . . . . ?
C19 C14 C15 C16 -2.4(3) . . . . ?
C20 C16 C17 C18 179.7(2) . . . . ?
C21 C18 C19 C14 174.3(2) . . . . ?
C22 C23 C24 F2 -179.7(2) . . . . ?
C22 C23 C24 C25 -0.3(4) . . . . ?
C23 C22 C27 F5 -178.6(2) . . . . ?
C23 C22 C27 C26 0.7(3) . . . . ?
C23 C24 C25 F3 179.3(2) . . . . ?
C23 C24 C25 C26 0.1(4) . . . . ?
C24 C25 C26 F4 179.7(2) . . . . ?
C24 C25 C26 C27 0.5(4) . . . . ?
C25 C26 C27 F5 178.4(2) . . . . ?
C25 C26 C27 C22 -0.9(4) . . . . ?
C27 C22 C23 F1 -178.5(2) . . . . ?
C27 C22 C23 C24 -0.1(3) . . . . ?

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.
####################################################################### 
# 
# 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_stu1119
_database_code_depnum_ccdc_archive 'CCDC 2234490'
loop_
_audit_author_name
_audit_author_address
'Ryota Sato'
;University of Tsukuba
Japan
;
_audit_update_record             
;
2023-01-05 deposited with the CCDC.	2023-05-04 downloaded from the CCDC.
;
_chemical_formula_moiety         'C38 H6 F20'
#==============================================================================
# CHEMICAL DATA
_chemical_formula_sum            'C38 H6 F20'
_chemical_formula_weight         842.43
_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 0.0033 0.0016
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
F F 0.0171 0.0103
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,1/2+Y,1/2-Z
3 -X,-Y,-Z
4 +X,-1/2-Y,-1/2+Z

#------------------------------------------------------------------------------
_cell_length_a                   11.645(4)
_cell_length_b                   12.590(4)
_cell_length_c                   20.483(7)
_cell_angle_alpha                90.0000
_cell_angle_beta                 95.087(5)
_cell_angle_gamma                90.0000
_cell_volume                     2991.2(17)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2072
_cell_measurement_theta_min      2.65
_cell_measurement_theta_max      26.34
_cell_measurement_temperature    120
_exptl_absorpt_coefficient_mu    0.196
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   
; 
SADABS V2008/1 (Bruker AXS) 
;
_exptl_absorpt_correction_T_min  0.4679
_exptl_absorpt_correction_T_max  0.7455
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.871
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
#------------------------------------------------------------------------------
_exptl_crystal_description       nONE
_exptl_crystal_F_000             1656.00
_exptl_crystal_size_max          0.177
_exptl_crystal_size_mid          0.029
_exptl_crystal_size_min          0.028
_diffrn_reflns_av_R_equivalents  0.0852
_diffrn_reflns_av_unetI/netI     0.1115
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            16382
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.097
_diffrn_reflns_theta_min         1.756
#==============================================================================
# EXPERIMENTAL DATA
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.986
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_radiation_source         'Bruker TXS fine-focus rotating anode'
_diffrn_radiation_monochromator  'Bruker Helios multilayer confocal mirror'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_ambient_temperature      120
_diffrn_detector_area_resol_mean 8.333
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count .
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3491
_reflns_number_total             6495
_reflns_threshold_expression     F²>2.0σ(F²)
_computing_cell_refinement       Unknown
#==============================================================================
_computing_data_collection       Unknown
_computing_data_reduction        Unknown
_computing_molecular_graphics    'CrystalStructure 4.3'
_computing_publication_material  'CrystalStructure 4.3 (Rigaku, 2019)'
_computing_structure_refinement  'SHELXL Version 2018/3 (Sheldrick, 2008)'
_computing_structure_solution    'SIR92 (Altomare, et al., 1994)'
_refine_diff_density_max         0.31
_refine_diff_density_min         -0.41
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.998
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_parameters     535
_refine_ls_number_reflns         6495
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1316
_refine_ls_R_factor_gt           0.0569
_refine_ls_shift/su_max          0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0543P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1148
_refine_ls_wR_factor_ref         0.1439
#==============================================================================
# REFINEMENT DATA
_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.63463(17) 0.85246(15) 0.97788(9) 0.0282(5) Uani 1 1 d . . . . .
F2 F 0.60222(17) 1.01926(15) 1.05524(9) 0.0291(5) Uani 1 1 d . . . . .
F3 F 0.77229(18) 1.07992(15) 1.14782(8) 0.0315(5) Uani 1 1 d . . . . .
F4 F 0.96695(18) 0.96013(16) 1.16877(9) 0.0331(5) Uani 1 1 d . . . . .
F5 F 0.99578(17) 0.78781(15) 1.09417(8) 0.0252(5) Uani 1 1 d . . . . .
F6 F 0.88759(18) 0.84011(15) 0.80645(8) 0.0292(5) Uani 1 1 d . . . . .
F7 F 1.0173(2) 0.89102(16) 0.70998(9) 0.0396(6) Uani 1 1 d . . . . .
F8 F 1.20530(18) 0.77159(17) 0.68776(9) 0.0362(6) Uani 1 1 d . . . . .
F9 F 1.25725(18) 0.59709(18) 0.76208(9) 0.0376(6) Uani 1 1 d . . . . .
F10 F 1.12790(18) 0.54437(16) 0.85937(8) 0.0316(5) Uani 1 1 d . . . . .
F11 F 0.85188(17) 0.19210(15) 1.02345(9) 0.0293(5) Uani 1 1 d . . . . .
F12 F 0.88901(17) 0.02231(15) 0.94896(9) 0.0292(5) Uani 1 1 d . . . . .
F13 F 0.72453(18) -0.04070(15) 0.85409(8) 0.0321(5) Uani 1 1 d . . . . .
F14 F 0.52633(19) 0.07321(16) 0.83203(9) 0.0342(5) Uani 1 1 d . . . . .
F15 F 0.49024(17) 0.24477(15) 0.90494(8) 0.0269(5) Uani 1 1 d . . . . .
F16 F 0.56799(19) 0.18005(15) 1.17799(9) 0.0340(6) Uani 1 1 d . . . . .
F17 F 0.4262(2) 0.12442(16) 1.26653(9) 0.0398(6) Uani 1 1 d . . . . .
F18 F 0.26006(19) 0.26105(17) 1.30108(9) 0.0387(6) Uani 1 1 d . . . . .
F19 F 0.23887(18) 0.45502(17) 1.24309(9) 0.0363(6) Uani 1 1 d . . . . .
F20 F 0.38018(17) 0.51361(15) 1.15433(8) 0.0276(5) Uani 1 1 d . . . . .
C1 C 0.8380(3) 0.7262(3) 0.98705(13) 0.0165(7) Uani 1 1 d . . . . .
C2 C 0.9050(3) 0.7458(3) 0.93667(14) 0.0191(8) Uani 1 1 d . . . . .
H1 H 0.933132 0.814077 0.931194 0.023 Uiso 1 1 calc R U . . .
C3 C 0.9325(3) 0.6646(3) 0.89260(14) 0.0163(7) Uani 1 1 d . . . . .
C4 C 0.8936(3) 0.5639(3) 0.90156(14) 0.0189(8) Uani 1 1 d . . . . .
H2 H 0.914472 0.509832 0.874004 0.023 Uiso 1 1 calc R U . . .
C5 C 0.8215(3) 0.5400(3) 0.95253(14) 0.0166(8) Uani 1 1 d . . . . .
C6 C 0.7755(3) 0.4384(3) 0.95891(14) 0.0186(8) Uani 1 1 d . . . . .
H3 H 0.796301 0.384588 0.931212 0.022 Uiso 1 1 calc R U . . .
C7 C 0.6993(3) 0.4158(2) 1.00561(13) 0.0153(7) Uani 1 1 d . . . . .
C8 C 0.6467(3) 0.3142(2) 1.01208(14) 0.0168(7) Uani 1 1 d . . . . .
C9 C 0.5771(3) 0.2953(3) 1.06062(14) 0.0182(8) Uani 1 1 d . . . . .
C10 C 0.5521(3) 0.3754(3) 1.10638(14) 0.0176(7) Uani 1 1 d . . . . .
C11 C 0.5962(3) 0.4745(3) 1.09987(14) 0.0182(8) Uani 1 1 d . . . . .
C12 C 0.6706(3) 0.4984(3) 1.04953(13) 0.0170(7) Uani 1 1 d . . . . .
C13 C 0.7173(3) 0.5998(3) 1.04379(14) 0.0185(8) Uani 1 1 d . . . . .
C14 C 0.7913(3) 0.6225(3) 0.99592(13) 0.0162(7) Uani 1 1 d . . . . .
C15 C 0.8169(3) 0.8153(2) 1.03321(14) 0.0162(7) Uani 1 1 d . . . . .
C16 C 0.7172(3) 0.8755(3) 1.02593(14) 0.0195(8) Uani 1 1 d . . . . .
C17 C 0.7005(3) 0.9623(3) 1.06505(15) 0.0201(8) Uani 1 1 d . . . . .
C18 C 0.7856(3) 0.9914(3) 1.11227(14) 0.0208(8) Uani 1 1 d . . . . .
C19 C 0.8841(3) 0.9323(3) 1.12202(14) 0.0198(8) Uani 1 1 d . . . . .
C20 C 0.8984(3) 0.8445(3) 1.08310(14) 0.0164(7) Uani 1 1 d . . . . .
C21 C 1.0037(3) 0.6913(3) 0.83750(14) 0.0185(8) Uani 1 1 d . . . . .
C22 C 0.9799(3) 0.7784(3) 0.79795(14) 0.0198(8) Uani 1 1 d . . . . .
C23 C 1.0457(3) 0.8054(3) 0.74770(15) 0.0232(8) Uani 1 1 d . . . . .
C24 C 1.1395(3) 0.7449(3) 0.73614(15) 0.0252(9) Uani 1 1 d . . . . .
C25 C 1.1658(3) 0.6570(3) 0.77377(15) 0.0230(8) Uani 1 1 d . . . . .
C26 C 1.0984(3) 0.6311(3) 0.82368(14) 0.0211(8) Uani 1 1 d . . . . .
C27 C 0.6708(3) 0.2250(2) 0.96665(14) 0.0162(7) Uani 1 1 d . . . . .
C28 C 0.7712(3) 0.1667(3) 0.97516(14) 0.0190(8) Uani 1 1 d . . . . .
C29 C 0.7907(3) 0.0783(3) 0.93718(15) 0.0206(8) Uani 1 1 d . . . . .
C30 C 0.7074(3) 0.0469(3) 0.88923(15) 0.0222(8) Uani 1 1 d . . . . .
C31 C 0.6073(3) 0.1037(3) 0.87868(15) 0.0221(8) Uani 1 1 d . . . . .
C32 C 0.5900(3) 0.1920(3) 0.91689(14) 0.0191(8) Uani 1 1 d . . . . .
C33 C 0.4773(3) 0.3477(3) 1.15953(14) 0.0192(8) Uani 1 1 d . . . . .
C34 C 0.4852(3) 0.2498(3) 1.19102(15) 0.0234(8) Uani 1 1 d . . . . .
C35 C 0.4137(3) 0.2203(3) 1.23742(15) 0.0250(9) Uani 1 1 d . . . . .
C36 C 0.3304(3) 0.2889(3) 1.25498(15) 0.0254(9) Uani 1 1 d . . . . .
C37 C 0.3202(3) 0.3866(3) 1.22605(15) 0.0228(8) Uani 1 1 d . . . . .
C38 C 0.3939(3) 0.4153(3) 1.17984(14) 0.0197(8) Uani 1 1 d . . . . .
H4 H 0.549(2) 0.231(2) 1.0635(13) 0.004(8) Uiso 1 1 d . . . . .
H5 H 0.585(3) 0.532(3) 1.1304(16) 0.035(10) Uiso 1 1 d . . . . .
H6 H 0.703(3) 0.653(3) 1.0751(16) 0.038(11) Uiso 1 1 d . . . . .


#==============================================================================
# MOLECULAR GEOMETRY
_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C16 1.346(4) . ?
F2 C17 1.350(4) . ?
F3 C18 1.348(4) . ?
F4 C19 1.344(4) . ?
F5 C20 1.342(4) . ?
F6 C22 1.349(4) . ?
F7 C23 1.351(4) . ?
F8 C24 1.347(3) . ?
F9 C25 1.344(4) . ?
F10 C26 1.341(4) . ?
F11 C28 1.341(4) . ?
F12 C29 1.348(4) . ?
F13 C30 1.341(3) . ?
F14 C31 1.338(4) . ?
F15 C32 1.342(4) . ?
F16 C34 1.348(4) . ?
F17 C35 1.348(4) . ?
F18 C36 1.350(3) . ?
F19 C37 1.348(4) . ?
F20 C38 1.347(4) . ?
C1 C2 1.370(4) . ?
C1 C14 1.432(4) . ?
C1 C15 1.501(4) . ?
C2 H1 0.9300 . ?
C2 C3 1.419(4) . ?
C3 C4 1.364(4) . ?
C3 C21 1.496(4) . ?
C4 H2 0.9300 . ?
C4 C5 1.429(4) . ?
C5 C6 1.397(4) . ?
C5 C14 1.432(4) . ?
C6 H3 0.9300 . ?
C6 C7 1.390(4) . ?
C7 C8 1.429(4) . ?
C7 C12 1.434(4) . ?
C8 C9 1.359(4) . ?
C8 C27 1.501(4) . ?
C9 C10 1.424(4) . ?
C9 H4 0.88(3) . ?
C10 C11 1.361(5) . ?
C10 C33 1.494(4) . ?
C11 C12 1.436(4) . ?
C11 H5 0.97(3) . ?
C12 C13 1.397(5) . ?
C13 C14 1.391(4) . ?
C13 H6 0.95(3) . ?
C15 C16 1.383(5) . ?
C15 C20 1.381(4) . ?
C16 C17 1.379(4) . ?
C17 C18 1.372(5) . ?
C18 C19 1.367(5) . ?
C19 C20 1.382(4) . ?
C21 C22 1.378(4) . ?
C21 C26 1.388(5) . ?
C22 C23 1.379(4) . ?
C23 C24 1.369(5) . ?
C24 C25 1.368(5) . ?
C25 C26 1.382(4) . ?
C27 C28 1.378(5) . ?
C27 C32 1.388(4) . ?
C28 C29 1.388(4) . ?
C29 C30 1.376(5) . ?
C30 C31 1.368(5) . ?
C31 C32 1.384(4) . ?
C33 C34 1.391(5) . ?
C33 C38 1.382(4) . ?
C34 C35 1.369(4) . ?
C35 C36 1.370(5) . ?
C36 C37 1.367(5) . ?
C37 C38 1.381(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C14 120.5(3) . . ?
C2 C1 C15 118.5(3) . . ?
C14 C1 C15 121.0(2) . . ?
C1 C2 H1 119.2 . . ?
C1 C2 C3 121.7(3) . . ?
C3 C2 H1 119.2 . . ?
C2 C3 C21 119.3(3) . . ?
C4 C3 C2 119.2(3) . . ?
C4 C3 C21 121.5(3) . . ?
C3 C4 H2 119.4 . . ?
C3 C4 C5 121.2(3) . . ?
C5 C4 H2 119.4 . . ?
C4 C5 C14 119.5(3) . . ?
C6 C5 C4 121.1(3) . . ?
C6 C5 C14 119.3(3) . . ?
C5 C6 H3 119.1 . . ?
C7 C6 C5 121.7(3) . . ?
C7 C6 H3 119.1 . . ?
C6 C7 C8 123.5(3) . . ?
C6 C7 C12 118.8(3) . . ?
C8 C7 C12 117.7(3) . . ?
C7 C8 C27 120.5(3) . . ?
C9 C8 C7 120.9(3) . . ?
C9 C8 C27 118.6(3) . . ?
C8 C9 C10 121.8(3) . . ?
C8 C9 H4 117.5(18) . . ?
C10 C9 H4 120.7(18) . . ?
C9 C10 C33 118.8(3) . . ?
C11 C10 C9 118.9(3) . . ?
C11 C10 C33 122.3(3) . . ?
C10 C11 C12 121.3(3) . . ?
C10 C11 H5 123(2) . . ?
C12 C11 H5 115(2) . . ?
C7 C12 C11 119.2(3) . . ?
C13 C12 C7 119.7(3) . . ?
C13 C12 C11 121.1(3) . . ?
C12 C13 H6 119(2) . . ?
C14 C13 C12 121.2(3) . . ?
C14 C13 H6 119(2) . . ?
C5 C14 C1 117.8(3) . . ?
C13 C14 C1 122.9(3) . . ?
C13 C14 C5 119.3(3) . . ?
C16 C15 C1 121.6(3) . . ?
C20 C15 C1 121.6(3) . . ?
C20 C15 C16 116.6(3) . . ?
F1 C16 C15 119.9(3) . . ?
F1 C16 C17 117.8(3) . . ?
C17 C16 C15 122.2(3) . . ?
F2 C17 C16 119.7(3) . . ?
F2 C17 C18 120.9(3) . . ?
C18 C17 C16 119.3(3) . . ?
F3 C18 C17 119.4(3) . . ?
F3 C18 C19 120.4(3) . . ?
C19 C18 C17 120.2(3) . . ?
F4 C19 C18 120.2(3) . . ?
F4 C19 C20 120.3(3) . . ?
C18 C19 C20 119.6(3) . . ?
F5 C20 C15 119.9(3) . . ?
F5 C20 C19 118.1(3) . . ?
C15 C20 C19 122.0(3) . . ?
C22 C21 C3 121.8(3) . . ?
C22 C21 C26 115.9(3) . . ?
C26 C21 C3 122.3(3) . . ?
F6 C22 C21 120.2(3) . . ?
F6 C22 C23 117.2(3) . . ?
C21 C22 C23 122.6(3) . . ?
F7 C23 C22 119.9(3) . . ?
F7 C23 C24 120.2(3) . . ?
C24 C23 C22 119.8(3) . . ?
F8 C24 C23 120.2(3) . . ?
F8 C24 C25 120.2(3) . . ?
C25 C24 C23 119.6(3) . . ?
F9 C25 C24 119.7(3) . . ?
F9 C25 C26 120.7(3) . . ?
C24 C25 C26 119.6(3) . . ?
F10 C26 C21 120.2(3) . . ?
F10 C26 C25 117.4(3) . . ?
C25 C26 C21 122.4(3) . . ?
C28 C27 C8 121.5(3) . . ?
C28 C27 C32 116.4(3) . . ?
C32 C27 C8 121.9(3) . . ?
F11 C28 C27 119.8(3) . . ?
F11 C28 C29 117.8(3) . . ?
C27 C28 C29 122.3(3) . . ?
F12 C29 C28 119.8(3) . . ?
F12 C29 C30 120.8(3) . . ?
C30 C29 C28 119.4(3) . . ?
F13 C30 C29 119.4(3) . . ?
F13 C30 C31 120.7(3) . . ?
C31 C30 C29 119.9(3) . . ?
F14 C31 C30 119.9(3) . . ?
F14 C31 C32 120.4(3) . . ?
C30 C31 C32 119.7(3) . . ?
F15 C32 C27 120.3(3) . . ?
F15 C32 C31 117.5(3) . . ?
C31 C32 C27 122.2(3) . . ?
C34 C33 C10 121.7(3) . . ?
C38 C33 C10 123.1(3) . . ?
C38 C33 C34 115.2(3) . . ?
F16 C34 C33 120.3(3) . . ?
F16 C34 C35 116.8(3) . . ?
C35 C34 C33 122.9(3) . . ?
F17 C35 C34 120.1(3) . . ?
F17 C35 C36 119.9(3) . . ?
C34 C35 C36 120.0(3) . . ?
F18 C36 C35 120.5(3) . . ?
F18 C36 C37 120.1(3) . . ?
C37 C36 C35 119.4(3) . . ?
F19 C37 C36 119.9(3) . . ?
F19 C37 C38 120.2(3) . . ?
C36 C37 C38 119.8(3) . . ?
F20 C38 C33 120.7(3) . . ?
F20 C38 C37 116.5(3) . . ?
C37 C38 C33 122.8(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
F1 C16 C17 F2 1.5(4) . . . . ?
F1 C16 C17 C18 -176.6(3) . . . . ?
F2 C17 C18 F3 -2.2(4) . . . . ?
F2 C17 C18 C19 179.4(3) . . . . ?
F3 C18 C19 F4 2.3(5) . . . . ?
F3 C18 C19 C20 -177.1(3) . . . . ?
F4 C19 C20 F5 1.0(4) . . . . ?
F4 C19 C20 C15 -177.9(3) . . . . ?
F6 C22 C23 F7 0.7(5) . . . . ?
F6 C22 C23 C24 -179.1(3) . . . . ?
F7 C23 C24 F8 1.1(5) . . . . ?
F7 C23 C24 C25 -178.5(3) . . . . ?
F8 C24 C25 F9 -0.3(5) . . . . ?
F8 C24 C25 C26 179.4(3) . . . . ?
F9 C25 C26 F10 -0.1(5) . . . . ?
F9 C25 C26 C21 179.6(3) . . . . ?
F11 C28 C29 F12 -1.0(4) . . . . ?
F11 C28 C29 C30 177.0(3) . . . . ?
F12 C29 C30 F13 0.2(4) . . . . ?
F12 C29 C30 C31 179.0(3) . . . . ?
F13 C30 C31 F14 -1.3(5) . . . . ?
F13 C30 C31 C32 178.0(3) . . . . ?
F14 C31 C32 F15 -0.3(4) . . . . ?
F14 C31 C32 C27 178.6(3) . . . . ?
F16 C34 C35 F17 -1.6(5) . . . . ?
F16 C34 C35 C36 177.5(3) . . . . ?
F17 C35 C36 F18 -0.4(5) . . . . ?
F17 C35 C36 C37 178.7(3) . . . . ?
F18 C36 C37 F19 -0.7(5) . . . . ?
F18 C36 C37 C38 178.8(3) . . . . ?
F19 C37 C38 F20 0.7(5) . . . . ?
F19 C37 C38 C33 -178.7(3) . . . . ?
C1 C2 C3 C4 -1.6(5) . . . . ?
C1 C2 C3 C21 178.5(3) . . . . ?
C1 C15 C16 F1 2.3(4) . . . . ?
C1 C15 C16 C17 -175.2(3) . . . . ?
C1 C15 C20 F5 -4.9(4) . . . . ?
C1 C15 C20 C19 174.0(3) . . . . ?
C2 C1 C14 C5 2.9(5) . . . . ?
C2 C1 C14 C13 -176.1(3) . . . . ?
C2 C1 C15 C16 97.5(4) . . . . ?
C2 C1 C15 C20 -79.2(4) . . . . ?
C2 C3 C4 C5 2.9(5) . . . . ?
C2 C3 C21 C22 -47.3(5) . . . . ?
C2 C3 C21 C26 131.7(4) . . . . ?
C3 C4 C5 C6 175.7(3) . . . . ?
C3 C4 C5 C14 -1.4(5) . . . . ?
C3 C21 C22 F6 -2.8(5) . . . . ?
C3 C21 C22 C23 178.8(3) . . . . ?
C3 C21 C26 F10 1.3(5) . . . . ?
C3 C21 C26 C25 -178.4(3) . . . . ?
C4 C3 C21 C22 132.8(4) . . . . ?
C4 C3 C21 C26 -48.2(5) . . . . ?
C4 C5 C6 C7 -175.8(3) . . . . ?
C4 C5 C14 C1 -1.6(5) . . . . ?
C4 C5 C14 C13 177.4(3) . . . . ?
C5 C6 C7 C8 177.4(3) . . . . ?
C5 C6 C7 C12 -2.0(5) . . . . ?
C6 C5 C14 C1 -178.6(3) . . . . ?
C6 C5 C14 C13 0.3(5) . . . . ?
C6 C7 C8 C9 176.9(3) . . . . ?
C6 C7 C8 C27 -0.9(5) . . . . ?
C6 C7 C12 C11 -177.2(3) . . . . ?
C6 C7 C12 C13 1.3(5) . . . . ?
C7 C8 C9 C10 0.9(5) . . . . ?
C7 C8 C27 C28 78.8(4) . . . . ?
C7 C8 C27 C32 -105.9(4) . . . . ?
C7 C12 C13 C14 0.2(5) . . . . ?
C8 C7 C12 C11 3.4(5) . . . . ?
C8 C7 C12 C13 -178.2(3) . . . . ?
C8 C9 C10 C11 2.2(5) . . . . ?
C8 C9 C10 C33 -178.4(3) . . . . ?
C8 C27 C28 F11 -2.6(4) . . . . ?
C8 C27 C28 C29 174.4(3) . . . . ?
C8 C27 C32 F15 4.9(4) . . . . ?
C8 C27 C32 C31 -174.0(3) . . . . ?
C9 C8 C27 C28 -99.1(4) . . . . ?
C9 C8 C27 C32 76.2(4) . . . . ?
C9 C10 C11 C12 -2.4(5) . . . . ?
C9 C10 C33 C34 38.4(5) . . . . ?
C9 C10 C33 C38 -139.8(3) . . . . ?
C10 C11 C12 C7 -0.4(5) . . . . ?
C10 C11 C12 C13 -178.8(3) . . . . ?
C10 C33 C34 F16 5.6(5) . . . . ?
C10 C33 C34 C35 -176.5(3) . . . . ?
C10 C33 C38 F20 -3.6(5) . . . . ?
C10 C33 C38 C37 175.8(3) . . . . ?
C11 C10 C33 C34 -142.2(4) . . . . ?
C11 C10 C33 C38 39.6(5) . . . . ?
C11 C12 C13 C14 178.6(3) . . . . ?
C12 C7 C8 C9 -3.7(5) . . . . ?
C12 C7 C8 C27 178.5(3) . . . . ?
C12 C13 C14 C1 177.9(3) . . . . ?
C12 C13 C14 C5 -1.0(5) . . . . ?
C14 C1 C2 C3 -1.4(5) . . . . ?
C14 C1 C15 C16 -83.6(4) . . . . ?
C14 C1 C15 C20 99.6(4) . . . . ?
C14 C5 C6 C7 1.2(5) . . . . ?
C15 C1 C2 C3 177.5(3) . . . . ?
C15 C1 C14 C5 -176.0(3) . . . . ?
C15 C1 C14 C13 5.1(5) . . . . ?
C15 C16 C17 F2 179.1(3) . . . . ?
C15 C16 C17 C18 0.9(5) . . . . ?
C16 C15 C20 F5 178.2(3) . . . . ?
C16 C15 C20 C19 -2.9(4) . . . . ?
C16 C17 C18 F3 176.0(3) . . . . ?
C16 C17 C18 C19 -2.5(5) . . . . ?
C17 C18 C19 F4 -179.3(3) . . . . ?
C17 C18 C19 C20 1.3(5) . . . . ?
C18 C19 C20 F5 -179.6(3) . . . . ?
C18 C19 C20 C15 1.5(5) . . . . ?
C20 C15 C16 F1 179.2(2) . . . . ?
C20 C15 C16 C17 1.7(4) . . . . ?
C21 C3 C4 C5 -177.2(3) . . . . ?
C21 C22 C23 F7 179.1(3) . . . . ?
C21 C22 C23 C24 -0.7(5) . . . . ?
C22 C21 C26 F10 -179.7(3) . . . . ?
C22 C21 C26 C25 0.6(5) . . . . ?
C22 C23 C24 F8 -179.0(3) . . . . ?
C22 C23 C24 C25 1.3(5) . . . . ?
C23 C24 C25 F9 179.4(3) . . . . ?
C23 C24 C25 C26 -1.0(5) . . . . ?
C24 C25 C26 F10 -179.7(3) . . . . ?
C24 C25 C26 C21 0.0(5) . . . . ?
C26 C21 C22 F6 178.2(3) . . . . ?
C26 C21 C22 C23 -0.2(5) . . . . ?
C27 C8 C9 C10 178.8(3) . . . . ?
C27 C28 C29 F12 -178.0(3) . . . . ?
C27 C28 C29 C30 -0.1(5) . . . . ?
C28 C27 C32 F15 -179.5(3) . . . . ?
C28 C27 C32 C31 1.6(4) . . . . ?
C28 C29 C30 F13 -177.7(3) . . . . ?
C28 C29 C30 C31 1.1(5) . . . . ?
C29 C30 C31 F14 180.0(3) . . . . ?
C29 C30 C31 C32 -0.7(5) . . . . ?
C30 C31 C32 F15 -179.6(3) . . . . ?
C30 C31 C32 C27 -0.7(5) . . . . ?
C32 C27 C28 F11 -178.2(2) . . . . ?
C32 C27 C28 C29 -1.2(4) . . . . ?
C33 C10 C11 C12 178.2(3) . . . . ?
C33 C34 C35 F17 -179.5(3) . . . . ?
C33 C34 C35 C36 -0.5(6) . . . . ?
C34 C33 C38 F20 178.1(3) . . . . ?
C34 C33 C38 C37 -2.6(5) . . . . ?
C34 C35 C36 F18 -179.4(3) . . . . ?
C34 C35 C36 C37 -0.4(5) . . . . ?
C35 C36 C37 F19 -179.7(3) . . . . ?
C35 C36 C37 C38 -0.3(5) . . . . ?
C36 C37 C38 F20 -178.8(3) . . . . ?
C36 C37 C38 C33 1.9(5) . . . . ?
C38 C33 C34 F16 -176.0(3) . . . . ?
C38 C33 C34 C35 1.9(5) . . . . ?

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.
