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

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_stu822
_database_code_depnum_ccdc_archive 'CCDC 2099539'
loop_
_audit_author_name
_audit_author_address
'Ryota Sato'
;University of Tsukuba
Japan
;
_audit_update_record             
;
2021-07-27 deposited with the CCDC.	2022-09-09 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        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
_space_group_IT_number           15
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
#------------------------------------------------------------------------------
_cell_length_a                   19.990(3)
_cell_length_b                   6.2622(10)
_cell_length_c                   13.262(2)
_cell_angle_alpha                90.0000
_cell_angle_beta                 95.966(2)
_cell_angle_gamma                90.0000
_cell_volume                     1651.1(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3350
_cell_measurement_theta_min      3.09
_cell_measurement_theta_max      27.06
_cell_measurement_temperature    120
#------------------------------------------------------------------------------
_exptl_crystal_description       nONE
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.134
_exptl_crystal_size_mid          0.069
_exptl_crystal_size_min          0.010
_exptl_crystal_density_diffrn    1.851
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             912.00
_exptl_absorpt_coefficient_mu    0.187
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.6811
_exptl_absorpt_correction_T_max  0.7455

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

_diffrn_ambient_temperature      120
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source         'Bruker TXS fine-focus rotating anode'
_diffrn_radiation_monochromator  'Bruker Helios multilayer confocal mirror'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_reflns_number            8998
_diffrn_reflns_av_unetI/netI     0.0181
_diffrn_reflns_av_R_equivalents  0.0247
_diffrn_reflns_theta_max         27.098
_diffrn_reflns_theta_min         2.049
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             1817
_reflns_number_gt                1511
_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          0.0609
_refine_ls_R_factor_gt           0.0510
_refine_ls_wR_factor_ref         0.1361
_refine_ls_wR_factor_gt          0.1283
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         1817
_refine_ls_number_parameters     145
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0615P)²+5.0524P] 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         0.87
_refine_diff_density_min         -0.30
_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
F2 F 0.64705(7) 0.1517(2) 0.54994(10) 0.0255(3) Uani 1 1 d . . . . .
F5 F 0.66262(7) 0.8010(2) 0.82260(10) 0.0262(3) Uani 1 1 d . . . . .
F3 F 0.72608(7) 0.4977(2) 0.52398(9) 0.0272(4) Uani 1 1 d . . . . .
F4 F 0.73278(7) 0.8214(2) 0.66141(10) 0.0283(4) Uani 1 1 d . . . . .
F1 F 0.57487(7) 0.1303(2) 0.70856(10) 0.0259(4) Uani 1 1 d . . . . .
C6 C 0.61551(10) 0.4648(4) 0.77193(15) 0.0181(5) Uani 1 1 d . . . . .
C7 C 0.61412(11) 0.3031(4) 0.70024(16) 0.0186(5) Uani 1 1 d . . . . .
C5 C 0.50298(11) 0.4054(4) 1.02955(16) 0.0190(5) Uani 1 1 d . . . . .
C8 C 0.65100(10) 0.3114(4) 0.61754(15) 0.0181(5) Uani 1 1 d . . . . .
C10 C 0.69342(11) 0.6514(4) 0.67291(16) 0.0195(5) Uani 1 1 d . . . . .
C4 C 0.54626(11) 0.2404(4) 1.00481(16) 0.0211(5) Uani 1 1 d . . . . .
H3 H 0.550584 0.117869 1.044543 0.025 Uiso 1 1 calc R U . . .
C3 C 0.58216(11) 0.2594(4) 0.92233(17) 0.0222(5) Uani 1 1 d . . . . .
H2 H 0.610394 0.149210 0.906271 0.027 Uiso 1 1 calc R U . . .
C9 C 0.69082(10) 0.4868(4) 0.60385(15) 0.0188(5) Uani 1 1 d . . . . .
C11 C 0.65637(11) 0.6390(4) 0.75537(16) 0.0189(5) Uani 1 1 d . . . . .
C1 C 0.53526(11) 0.6105(4) 0.88535(16) 0.0210(5) Uani 1 1 d . . . . .
H1 H 0.532165 0.733594 0.845884 0.025 Uiso 1 1 calc R U . . .
C2 C 0.57631(11) 0.4477(4) 0.86110(16) 0.0203(5) Uani 1 1 d . . . . .


#==============================================================================
_computing_data_collection       Unknown
_computing_cell_refinement       Unknown
_computing_data_reduction        Unknown
_computing_structure_solution    SIR97
_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
F2 C8 1.340(2) . ?
F5 C11 1.348(2) . ?
F3 C9 1.334(2) . ?
F4 C10 1.342(3) . ?
F1 C7 1.348(3) . ?
C6 C7 1.387(3) . ?
C6 C11 1.394(3) . ?
C6 C2 1.489(3) . ?
C7 C8 1.384(3) . ?
C5 C4 1.408(3) . ?
C5 C5 1.418(4) 5_667 ?
C5 C1 1.431(3) 5_667 ?
C8 C9 1.379(3) . ?
C10 C9 1.376(3) . ?
C10 C11 1.385(3) . ?
C4 C3 1.374(3) . ?
C4 H3 0.9300 . ?
C3 C2 1.430(3) . ?
C3 H2 0.9300 . ?
C1 C2 1.368(3) . ?
C1 H1 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C7 C6 C11 115.69(19) . . ?
C7 C6 C2 121.2(2) . . ?
C11 C6 C2 123.1(2) . . ?
F1 C7 C8 117.20(19) . . ?
F1 C7 C6 120.01(18) . . ?
C8 C7 C6 122.8(2) . . ?
C4 C5 C5 120.2(3) . 5_667 ?
C4 C5 C1 121.6(2) . 5_667 ?
C5 C5 C1 118.2(3) 5_667 5_667 ?
F2 C8 C9 120.06(18) . . ?
F2 C8 C7 120.2(2) . . ?
C9 C8 C7 119.7(2) . . ?
F4 C10 C9 120.03(19) . . ?
F4 C10 C11 120.1(2) . . ?
C9 C10 C11 119.8(2) . . ?
C3 C4 C5 120.4(2) . . ?
C3 C4 H3 119.8 . . ?
C5 C4 H3 119.8 . . ?
C4 C3 C2 120.3(2) . . ?
C4 C3 H2 119.8 . . ?
C2 C3 H2 119.8 . . ?
F3 C9 C10 120.2(2) . . ?
F3 C9 C8 120.3(2) . . ?
C10 C9 C8 119.41(19) . . ?
F5 C11 C10 117.4(2) . . ?
F5 C11 C6 120.03(18) . . ?
C10 C11 C6 122.6(2) . . ?
C2 C1 C5 121.1(2) . 5_667 ?
C2 C1 H1 119.5 . . ?
C5 C1 H1 119.5 5_667 . ?
C1 C2 C3 119.8(2) . . ?
C1 C2 C6 120.7(2) . . ?
C3 C2 C6 119.4(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
C11 C6 C7 F1 -178.51(19) . . . . ?
C2 C6 C7 F1 2.5(3) . . . . ?
C11 C6 C7 C8 0.4(3) . . . . ?
C2 C6 C7 C8 -178.6(2) . . . . ?
F1 C7 C8 F2 -0.2(3) . . . . ?
C6 C7 C8 F2 -179.15(19) . . . . ?
F1 C7 C8 C9 178.49(19) . . . . ?
C6 C7 C8 C9 -0.5(3) . . . . ?
C5 C5 C4 C3 -1.2(4) 5_667 . . . ?
C1 C5 C4 C3 179.7(2) 5_667 . . . ?
C5 C4 C3 C2 0.4(3) . . . . ?
F4 C10 C9 F3 -1.6(3) . . . . ?
C11 C10 C9 F3 179.70(19) . . . . ?
F4 C10 C9 C8 178.93(19) . . . . ?
C11 C10 C9 C8 0.2(3) . . . . ?
F2 C8 C9 F3 -0.6(3) . . . . ?
C7 C8 C9 F3 -179.35(19) . . . . ?
F2 C8 C9 C10 178.81(19) . . . . ?
C7 C8 C9 C10 0.1(3) . . . . ?
F4 C10 C11 F5 -1.0(3) . . . . ?
C9 C10 C11 F5 177.67(19) . . . . ?
F4 C10 C11 C6 -178.98(19) . . . . ?
C9 C10 C11 C6 -0.3(3) . . . . ?
C7 C6 C11 F5 -177.93(19) . . . . ?
C2 C6 C11 F5 1.0(3) . . . . ?
C7 C6 C11 C10 0.0(3) . . . . ?
C2 C6 C11 C10 178.9(2) . . . . ?
C5 C1 C2 C3 -1.0(3) 5_667 . . . ?
C5 C1 C2 C6 179.50(19) 5_667 . . . ?
C4 C3 C2 C1 0.6(3) . . . . ?
C4 C3 C2 C6 -179.8(2) . . . . ?
C7 C6 C2 C1 -129.8(2) . . . . ?
C11 C6 C2 C1 51.3(3) . . . . ?
C7 C6 C2 C3 50.7(3) . . . . ?
C11 C6 C2 C3 -128.3(2) . . . . ?


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





#==============================================================================
#     End of 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_global
_database_code_depnum_ccdc_archive 'CCDC 2114882'
loop_
_audit_author_name
_audit_author_address
'Ryota Sato'
;University of Tsukuba
Japan
;
_audit_update_record             
;
2021-10-11 deposited with the CCDC.	2022-09-09 downloaded from the CCDC.
;
_audit_creation_date             2021-10-08
_audit_creation_method           'by CrystalStructure 4.3'

#==============================================================================

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

_chemical_formula_sum            'C13 H4 F5'
_chemical_formula_moiety         'C13 H4 F5'
_chemical_formula_weight         255.17
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
_space_group_IT_number           15
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
#------------------------------------------------------------------------------
_cell_length_a                   22.572(5)
_cell_length_b                   6.5859(15)
_cell_length_c                   13.304(3)
_cell_angle_alpha                90.0000
_cell_angle_beta                 106.248(3)
_cell_angle_gamma                90.0000
_cell_volume                     1898.7(8)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    1427
_cell_measurement_theta_min      3.19
_cell_measurement_theta_max      26.77
_cell_measurement_temperature    120
#------------------------------------------------------------------------------
_exptl_crystal_description       nONE
_exptl_crystal_colour            nONE
_exptl_crystal_size_max          0.037
_exptl_crystal_size_mid          0.037
_exptl_crystal_size_min          0.009
_exptl_crystal_density_diffrn    1.785
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1016.00
_exptl_absorpt_coefficient_mu    0.172
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.6090
_exptl_absorpt_correction_T_max  0.7456

#==============================================================================
# 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_reflns_number            4351
_diffrn_reflns_av_unetI/netI     0.0389
_diffrn_reflns_av_R_equivalents  0.0312
_diffrn_reflns_theta_max         25.014
_diffrn_reflns_theta_min         1.880
_diffrn_reflns_theta_full        25.014
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             1671
_reflns_number_gt                1348
_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          0.0496
_refine_ls_R_factor_gt           0.0371
_refine_ls_wR_factor_ref         0.0934
_refine_ls_wR_factor_gt          0.0855
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_number_reflns         1671
_refine_ls_number_parameters     179
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0460P)²+1.2687P] 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         0.19
_refine_diff_density_min         -0.24
_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 0.10415(5) -0.37119(17) 0.16546(9) 0.0234(3) Uani 1 1 d . . . . .
F2 F 0.16779(6) -0.31656(18) 0.02560(9) 0.0251(3) Uani 1 1 d . . . . .
F3 F 0.22964(5) 0.03646(19) 0.02134(9) 0.0253(3) Uani 1 1 d . . . . .
F4 F 0.22700(5) 0.33490(17) 0.16122(9) 0.0252(3) Uani 1 1 d . . . . .
F5 F 0.16813(5) 0.27987(17) 0.30690(9) 0.0241(3) Uani 1 1 d . . . . .
C1 C 0.06374(9) 0.0672(3) 0.34657(15) 0.0167(5) Uani 1 1 d . . . . .
C2 C 0.09996(9) -0.0811(3) 0.32288(15) 0.0171(5) Uani 1 1 d . . . . .
C3 C 0.10635(9) -0.2710(3) 0.37761(16) 0.0180(5) Uani 1 1 d . . . . .
C4 C 0.07639(9) -0.3052(3) 0.45130(16) 0.0182(5) Uani 1 1 d . . . . .
C5 C 0.03751(9) -0.1547(3) 0.47686(15) 0.0160(4) Uani 1 1 d . . . . .
C6 C -0.00642(9) 0.1862(3) 0.44782(16) 0.0169(5) Uani 1 1 d . . . . .
C7 C 0.03127(9) 0.0367(3) 0.42310(15) 0.0161(5) Uani 1 1 d . . . . .
C8 C 0.13330(9) -0.0481(3) 0.24257(15) 0.0168(5) Uani 1 1 d . . . . .
C9 C 0.13538(9) -0.1952(3) 0.16846(15) 0.0173(5) Uani 1 1 d . . . . .
C10 C 0.16736(9) -0.1696(3) 0.09514(15) 0.0184(5) Uani 1 1 d . . . . .
C11 C 0.19853(9) 0.0092(3) 0.09216(15) 0.0186(5) Uani 1 1 d . . . . .
C12 C 0.19696(9) 0.1598(3) 0.16323(16) 0.0185(5) Uani 1 1 d . . . . .
C13 C 0.16549(9) 0.1300(3) 0.23664(15) 0.0176(5) Uani 1 1 d . . . . .
H1 H 0.0577(9) 0.196(3) 0.3100(16) 0.022(6) Uiso 1 1 d . . . . .
H2 H 0.1340(10) -0.368(3) 0.3637(16) 0.021(6) Uiso 1 1 d . . . . .
H3 H 0.0804(10) -0.428(3) 0.4873(17) 0.025(6) Uiso 1 1 d . . . . .
H4 H -0.0108(8) 0.310(3) 0.4113(14) 0.010(5) Uiso 1 1 d . . . . .


#==============================================================================
_computing_data_collection       Unknown
_computing_cell_refinement       Unknown
_computing_data_reduction        Unknown
_computing_structure_solution    'SIR2002 (Burla, et al., 2003)'
_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 C9 1.351(2) . ?
F2 C10 1.341(2) . ?
F3 C11 1.335(2) . ?
F4 C12 1.342(2) . ?
F5 C13 1.349(2) . ?
C1 C2 1.366(3) . ?
C1 C7 1.425(3) . ?
C1 H1 0.97(2) . ?
C2 C3 1.434(3) . ?
C2 C8 1.485(3) . ?
C3 C4 1.357(3) . ?
C3 H2 0.95(2) . ?
C4 C5 1.427(3) . ?
C4 H3 0.93(2) . ?
C5 C6 1.390(3) 5_556 ?
C5 C7 1.437(3) . ?
C6 C7 1.399(3) . ?
C6 H4 0.94(2) . ?
C8 C9 1.393(3) . ?
C8 C13 1.394(3) . ?
C9 C10 1.377(3) . ?
C10 C11 1.378(3) . ?
C11 C12 1.378(3) . ?
C12 C13 1.373(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
C2 C1 C7 121.66(19) . . ?
C2 C1 H1 121.4(12) . . ?
C7 C1 H1 116.9(12) . . ?
C1 C2 C3 119.21(18) . . ?
C1 C2 C8 121.21(18) . . ?
C3 C2 C8 119.58(18) . . ?
C4 C3 C2 120.81(19) . . ?
C4 C3 H2 121.2(13) . . ?
C2 C3 H2 117.8(13) . . ?
C3 C4 C5 121.4(2) . . ?
C3 C4 H3 121.4(13) . . ?
C5 C4 H3 117.2(13) . . ?
C6 C5 C4 122.42(19) 5_556 . ?
C6 C5 C7 119.40(18) 5_556 . ?
C4 C5 C7 118.18(18) . . ?
C5 C6 C7 121.81(19) 5_556 . ?
C5 C6 H4 120.1(12) 5_556 . ?
C7 C6 H4 118.0(12) . . ?
C6 C7 C1 122.48(19) . . ?
C6 C7 C5 118.79(18) . . ?
C1 C7 C5 118.73(18) . . ?
C9 C8 C13 115.11(18) . . ?
C9 C8 C2 122.14(18) . . ?
C13 C8 C2 122.74(18) . . ?
F1 C9 C10 117.18(17) . . ?
F1 C9 C8 119.80(17) . . ?
C10 C9 C8 123.01(18) . . ?
F2 C10 C9 120.47(18) . . ?
F2 C10 C11 119.65(18) . . ?
C9 C10 C11 119.88(18) . . ?
F3 C11 C12 120.48(18) . . ?
F3 C11 C10 120.56(18) . . ?
C12 C11 C10 118.96(18) . . ?
F4 C12 C13 120.14(18) . . ?
F4 C12 C11 119.66(17) . . ?
C13 C12 C11 120.20(18) . . ?
F5 C13 C12 117.18(18) . . ?
F5 C13 C8 119.96(17) . . ?
C12 C13 C8 122.84(19) . . ?

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
C7 C1 C2 C3 -1.1(3) . . . . ?
C7 C1 C2 C8 179.64(17) . . . . ?
C1 C2 C3 C4 0.8(3) . . . . ?
C8 C2 C3 C4 -179.96(19) . . . . ?
C2 C3 C4 C5 0.1(3) . . . . ?
C3 C4 C5 C6 -179.9(2) . . . 5_556 ?
C3 C4 C5 C7 -0.7(3) . . . . ?
C5 C6 C7 C1 -179.59(18) 5_556 . . . ?
C5 C6 C7 C5 0.4(3) 5_556 . . . ?
C2 C1 C7 C6 -179.49(19) . . . . ?
C2 C1 C7 C5 0.5(3) . . . . ?
C6 C5 C7 C6 -0.4(3) 5_556 . . . ?
C4 C5 C7 C6 -179.62(18) . . . . ?
C6 C5 C7 C1 179.60(18) 5_556 . . . ?
C4 C5 C7 C1 0.4(3) . . . . ?
C1 C2 C8 C9 -136.6(2) . . . . ?
C3 C2 C8 C9 44.1(3) . . . . ?
C1 C2 C8 C13 44.4(3) . . . . ?
C3 C2 C8 C13 -134.9(2) . . . . ?
C13 C8 C9 F1 -178.03(17) . . . . ?
C2 C8 C9 F1 2.9(3) . . . . ?
C13 C8 C9 C10 0.8(3) . . . . ?
C2 C8 C9 C10 -178.26(18) . . . . ?
F1 C9 C10 F2 -1.2(3) . . . . ?
C8 C9 C10 F2 179.98(17) . . . . ?
F1 C9 C10 C11 177.99(18) . . . . ?
C8 C9 C10 C11 -0.9(3) . . . . ?
F2 C10 C11 F3 -0.7(3) . . . . ?
C9 C10 C11 F3 -179.85(17) . . . . ?
F2 C10 C11 C12 179.13(17) . . . . ?
C9 C10 C11 C12 0.0(3) . . . . ?
F3 C11 C12 F4 -0.1(3) . . . . ?
C10 C11 C12 F4 -179.90(18) . . . . ?
F3 C11 C12 C13 -179.24(17) . . . . ?
C10 C11 C12 C13 0.9(3) . . . . ?
F4 C12 C13 F5 -2.1(3) . . . . ?
C11 C12 C13 F5 177.05(17) . . . . ?
F4 C12 C13 C8 179.83(18) . . . . ?
C11 C12 C13 C8 -1.0(3) . . . . ?
C9 C8 C13 F5 -177.86(17) . . . . ?
C2 C8 C13 F5 1.2(3) . . . . ?
C9 C8 C13 C12 0.2(3) . . . . ?
C2 C8 C13 C12 179.20(18) . . . . ?


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



