# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_2cf3p_1
_database_code_depnum_ccdc_archive 'CCDC 1476942'
_audit_update_record             
;
2017-02-14 deposited with the CCDC.
2017-02-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H12 F6'
_chemical_formula_sum            'C24 H12 F6'
_chemical_formula_weight         414.34

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_space_group_name_Hall           '-P 2ybc'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   14.5068(11)
_cell_length_b                   16.0241(12)
_cell_length_c                   7.2760(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 96.4910(10)
_cell_angle_gamma                90.00
_cell_volume                     1680.5(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    12852
_cell_measurement_theta_min      2.43
_cell_measurement_theta_max      32.00

_exptl_crystal_description       block
_exptl_crystal_colour            blue
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.180
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.638
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             840
_exptl_absorpt_coefficient_mu    0.141
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.89914
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ccd
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12852
_diffrn_reflns_av_R_equivalents  0.0294
_diffrn_reflns_av_sigmaI/netI    0.0394
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         1.41
_diffrn_reflns_theta_max         31.30
_reflns_number_total             5059
_reflns_number_gt                3546
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5059
_refine_ls_number_parameters     271
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0767
_refine_ls_R_factor_gt           0.0482
_refine_ls_wR_factor_ref         0.1575
_refine_ls_wR_factor_gt          0.1377
_refine_ls_goodness_of_fit_ref   0.999
_refine_ls_restrained_S_all      0.999
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.97170(7) 0.71155(7) 0.53024(18) 0.0377(3) Uani 1 1 d . . .
F2 F 0.99631(7) 0.64052(9) 0.78197(15) 0.0434(4) Uani 1 1 d . . .
F3 F 0.96485(6) 0.58106(6) 0.51872(14) 0.0265(2) Uani 1 1 d . . .
F4 F 0.51052(7) 0.64445(8) 0.83363(14) 0.0342(3) Uani 1 1 d . . .
F5 F 0.50808(6) 0.57775(6) 0.57752(14) 0.0236(2) Uani 1 1 d . . .
F6 F 0.50378(7) 0.70925(6) 0.57315(17) 0.0327(3) Uani 1 1 d . . .
C1 C 0.69745(11) 1.02793(10) 0.7424(2) 0.0215(3) Uani 1 1 d . . .
H1 H 0.6677 1.0775 0.7663 0.026 Uiso 1 1 calc R . .
C2 C 0.65092(11) 0.95469(10) 0.7432(2) 0.0193(3) Uani 1 1 d . . .
H2 H 0.5891 0.9546 0.7660 0.023 Uiso 1 1 calc R . .
C3 C 0.69564(10) 0.87743(10) 0.70932(19) 0.0165(3) Uani 1 1 d . . .
C4 C 0.65091(10) 0.80170(10) 0.7112(2) 0.0167(3) Uani 1 1 d . . .
H4 H 0.5887 0.8012 0.7312 0.020 Uiso 1 1 calc R . .
C5 C 0.69511(10) 0.72459(10) 0.68425(19) 0.0152(3) Uani 1 1 d . . .
C6 C 0.64922(10) 0.64741(9) 0.6865(2) 0.0150(3) Uani 1 1 d . . .
C7 C 0.69828(10) 0.57148(10) 0.70667(19) 0.0160(3) Uani 1 1 d . . .
C8 C 0.65672(10) 0.49591(10) 0.7535(2) 0.0173(3) Uani 1 1 d . . .
H8 H 0.5938 0.4959 0.7676 0.021 Uiso 1 1 calc R . .
C9 C 0.70534(10) 0.42213(10) 0.7792(2) 0.0174(3) Uani 1 1 d . . .
C10 C 0.66372(11) 0.34727(10) 0.8390(2) 0.0206(3) Uani 1 1 d . . .
H10 H 0.6010 0.3470 0.8549 0.025 Uiso 1 1 calc R . .
C11 C 0.71447(11) 0.27672(11) 0.8729(2) 0.0236(3) Uani 1 1 d . . .
H11 H 0.6866 0.2289 0.9135 0.028 Uiso 1 1 calc R . .
C12 C 0.81058(11) 0.27556(11) 0.8465(2) 0.0244(3) Uani 1 1 d . . .
H12 H 0.8447 0.2268 0.8696 0.029 Uiso 1 1 calc R . .
C13 C 0.79226(11) 1.02941(11) 0.7047(2) 0.0222(3) Uani 1 1 d . . .
H13 H 0.8233 1.0801 0.7026 0.027 Uiso 1 1 calc R . .
C14 C 0.83716(11) 0.95799(10) 0.6723(2) 0.0200(3) Uani 1 1 d . . .
H14 H 0.8986 0.9602 0.6473 0.024 Uiso 1 1 calc R . .
C15 C 0.79134(10) 0.87890(10) 0.6761(2) 0.0169(3) Uani 1 1 d . . .
C16 C 0.85260(11) 0.34474(10) 0.7879(2) 0.0216(3) Uani 1 1 d . . .
H16 H 0.9149 0.3425 0.7693 0.026 Uiso 1 1 calc R . .
C17 C 0.80222(11) 0.42128(10) 0.7543(2) 0.0180(3) Uani 1 1 d . . .
C18 C 0.84489(10) 0.49427(10) 0.7095(2) 0.0180(3) Uani 1 1 d . . .
H18 H 0.9076 0.4928 0.6937 0.022 Uiso 1 1 calc R . .
C19 C 0.79722(10) 0.57144(10) 0.68647(19) 0.0155(3) Uani 1 1 d . . .
C20 C 0.84035(10) 0.64807(9) 0.6510(2) 0.0156(3) Uani 1 1 d . . .
C21 C 0.79405(9) 0.72536(10) 0.66085(19) 0.0154(3) Uani 1 1 d . . .
C22 C 0.83716(10) 0.80457(10) 0.6538(2) 0.0175(3) Uani 1 1 d . . .
H22 H 0.8992 0.8066 0.6332 0.021 Uiso 1 1 calc R . .
C23 C 0.94273(11) 0.64560(10) 0.6212(2) 0.0199(3) Uani 1 1 d . . .
C24 C 0.54375(10) 0.64506(10) 0.6693(2) 0.0182(3) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C23 1.3397(19) . ?
F2 C23 1.3315(19) . ?
F3 C23 1.3354(18) . ?
F4 C24 1.3390(19) . ?
F5 C24 1.3412(17) . ?
F6 C24 1.3385(18) . ?
C1 C2 1.354(2) . ?
C1 C13 1.433(2) . ?
C1 H1 0.9300 . ?
C2 C3 1.432(2) . ?
C2 H2 0.9300 . ?
C3 C4 1.377(2) . ?
C3 C15 1.436(2) . ?
C4 C5 1.416(2) . ?
C4 H4 0.9300 . ?
C5 C6 1.405(2) . ?
C5 C21 1.4644(19) . ?
C6 C7 1.409(2) . ?
C6 C24 1.521(2) . ?
C7 C8 1.412(2) . ?
C7 C19 1.459(2) . ?
C8 C9 1.379(2) . ?
C8 H8 0.9300 . ?
C9 C10 1.433(2) . ?
C9 C17 1.437(2) . ?
C10 C11 1.356(2) . ?
C10 H10 0.9300 . ?
C11 C12 1.429(2) . ?
C11 H11 0.9300 . ?
C12 C16 1.357(2) . ?
C12 H12 0.9300 . ?
C13 C14 1.351(2) . ?
C13 H13 0.9300 . ?
C14 C15 1.433(2) . ?
C14 H14 0.9300 . ?
C15 C22 1.382(2) . ?
C16 C17 1.434(2) . ?
C16 H16 0.9300 . ?
C17 C18 1.380(2) . ?
C18 C19 1.417(2) . ?
C18 H18 0.9300 . ?
C19 C20 1.415(2) . ?
C20 C21 1.415(2) . ?
C20 C23 1.526(2) . ?
C21 C22 1.419(2) . ?
C22 H22 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
C2 C1 C13 120.33(15) . . ?
C2 C1 H1 119.8 . . ?
C13 C1 H1 119.8 . . ?
C1 C2 C3 120.85(14) . . ?
C1 C2 H2 119.6 . . ?
C3 C2 H2 119.6 . . ?
C4 C3 C2 122.48(14) . . ?
C4 C3 C15 118.80(14) . . ?
C2 C3 C15 118.70(14) . . ?
C3 C4 C5 123.11(13) . . ?
C3 C4 H4 118.4 . . ?
C5 C4 H4 118.4 . . ?
C6 C5 C4 122.93(13) . . ?
C6 C5 C21 118.72(14) . . ?
C4 C5 C21 118.29(14) . . ?
C5 C6 C7 121.79(13) . . ?
C5 C6 C24 119.61(13) . . ?
C7 C6 C24 118.60(13) . . ?
C6 C7 C8 122.79(13) . . ?
C6 C7 C19 118.75(14) . . ?
C8 C7 C19 118.40(14) . . ?
C9 C8 C7 122.86(13) . . ?
C9 C8 H8 118.6 . . ?
C7 C8 H8 118.6 . . ?
C8 C9 C10 122.18(14) . . ?
C8 C9 C17 118.92(14) . . ?
C10 C9 C17 118.82(14) . . ?
C11 C10 C9 120.95(15) . . ?
C11 C10 H10 119.5 . . ?
C9 C10 H10 119.5 . . ?
C10 C11 C12 120.28(16) . . ?
C10 C11 H11 119.9 . . ?
C12 C11 H11 119.9 . . ?
C16 C12 C11 120.76(16) . . ?
C16 C12 H12 119.6 . . ?
C11 C12 H12 119.6 . . ?
C14 C13 C1 120.77(15) . . ?
C14 C13 H13 119.6 . . ?
C1 C13 H13 119.6 . . ?
C13 C14 C15 120.82(15) . . ?
C13 C14 H14 119.6 . . ?
C15 C14 H14 119.6 . . ?
C22 C15 C14 121.99(14) . . ?
C22 C15 C3 119.50(14) . . ?
C14 C15 C3 118.49(14) . . ?
C12 C16 C17 120.92(15) . . ?
C12 C16 H16 119.5 . . ?
C17 C16 H16 119.5 . . ?
C18 C17 C16 122.12(14) . . ?
C18 C17 C9 119.54(14) . . ?
C16 C17 C9 118.25(14) . . ?
C17 C18 C19 122.80(14) . . ?
C17 C18 H18 118.6 . . ?
C19 C18 H18 118.6 . . ?
C20 C19 C18 123.97(13) . . ?
C20 C19 C7 118.56(14) . . ?
C18 C19 C7 117.44(14) . . ?
C21 C20 C19 121.89(13) . . ?
C21 C20 C23 120.36(13) . . ?
C19 C20 C23 117.45(13) . . ?
C20 C21 C22 124.60(13) . . ?
C20 C21 C5 118.41(14) . . ?
C22 C21 C5 116.98(13) . . ?
C15 C22 C21 123.16(14) . . ?
C15 C22 H22 118.4 . . ?
C21 C22 H22 118.4 . . ?
F2 C23 F3 106.86(13) . . ?
F2 C23 F1 107.32(14) . . ?
F3 C23 F1 103.07(13) . . ?
F2 C23 C20 110.97(13) . . ?
F3 C23 C20 113.51(13) . . ?
F1 C23 C20 114.49(13) . . ?
F6 C24 F4 107.09(13) . . ?
F6 C24 F5 103.76(12) . . ?
F4 C24 F5 106.32(12) . . ?
F6 C24 C6 113.35(13) . . ?
F4 C24 C6 112.75(12) . . ?
F5 C24 C6 112.89(12) . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        31.30
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.627
_refine_diff_density_min         -0.497
_refine_diff_density_rms         0.066
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: CHCl3/MeOH'
####################################################################### 
# 
# 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_new
_database_code_depnum_ccdc_archive 'CCDC 1525732'
_audit_update_record             
;
2017-02-13 deposited with the CCDC.
2017-02-15 downloaded from the CCDC.
;
_audit_creation_date             2017-02-11
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.01.04 svn.r3372 for OlexSys, GUI svn.r5292)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C23 H8 F20'
_chemical_formula_sum            'C23 H8 F20'
_chemical_formula_weight         664.29
_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 Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   16.244(6)
_cell_length_b                   11.619(4)
_cell_length_c                   12.748(5)
_cell_angle_alpha                90
_cell_angle_beta                 73.966(6)
_cell_angle_gamma                90
_cell_volume                     2312.4(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    123.1500
_cell_measurement_reflns_used    6022
_cell_measurement_theta_min      3.1440
_cell_measurement_theta_max      27.4894
_exptl_absorpt_coefficient_mu    0.225
_exptl_absorpt_correction_T_max  0.9860
_exptl_absorpt_correction_T_min  0.9655
_exptl_absorpt_correction_type   Numerical
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.908
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1304
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.08
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.1661
_diffrn_reflns_av_unetI/netI     0.1017
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            13312
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_ambient_temperature      123.1500
_diffrn_radiation_wavelength     0.710747
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Rotating Anode'
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_detector       CCD
_diffrn_measurement_device       'Saturn724+ (4x4 bin mode)'
_diffrn_source_power             1.2000
_diffrn_source_voltage           50.0000
_diffrn_source_current           24.0000
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measurement_method       dtprofit.ref
_diffrn_reflns_theta_full        27.4894
_diffrn_reflns_theta_min         3.1440
_diffrn_reflns_theta_max         27.4894
_diffrn_reflns_reduction_process 'Lp corrections applied'
_diffrn_measurement_details      
;
scan:
	Number of images: 360
	           Slice: -110.0000 - 70.0000
	     Image width: 0.5000
	        Exp time: 1.5000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: 0.0000
	             XTD: 45.3980
	          2theta: -20.0357
scan:
	Number of images: 360
	           Slice: -110.0000 - 70.0000
	     Image width: 0.5000
	        Exp time: 1.5000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: 90.0000
	             XTD: 45.3980
	          2theta: -20.0357

;
_diffrn_measurement_device_details 
;
AFC10: Fixed Chi 2 circle
;
_diffrn_orient_matrix_UB_11      0.0577
_diffrn_orient_matrix_UB_12      0.0574
_diffrn_orient_matrix_UB_13      0.0057
_diffrn_orient_matrix_UB_21      0.0188
_diffrn_orient_matrix_UB_22      -0.0267
_diffrn_orient_matrix_UB_23      0.0796
_diffrn_orient_matrix_UB_31      0.0539
_diffrn_orient_matrix_UB_32      -0.0269
_diffrn_orient_matrix_UB_33      -0.0217
_diffrn_orient_matrix_type       d*Trek
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2546
_reflns_number_total             3298
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2008)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.307
_refine_diff_density_min         -0.351
_refine_diff_density_rms         0.077
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     420
_refine_ls_number_reflns         3298
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0807
_refine_ls_R_factor_gt           0.0579
_refine_ls_restrained_S_all      1.050
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0506P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1249
_refine_ls_wR_factor_ref         0.1384
_refine_special_details          ?
_olex2_refinement_description    
;
;
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F5 F 0.80299(12) 0.81193(18) 0.49723(17) 0.0243(5) Uani 1 1 d . . . . .
F9 F 0.68219(13) 0.7705(2) 0.68484(17) 0.0309(6) Uani 1 1 d . . . . .
F4 F 0.75158(12) 0.73977(18) 0.37303(17) 0.0274(6) Uani 1 1 d . . . . .
F12 F 0.49721(13) 0.7941(2) 0.76065(19) 0.0370(6) Uani 1 1 d . . . . .
F1 F 1.13713(12) 0.5804(2) 0.11069(18) 0.0355(6) Uani 1 1 d . . . . .
F6 F 0.68887(12) 0.55959(19) 0.48792(18) 0.0337(6) Uani 1 1 d . . . . .
F8 F 0.61600(12) 0.7787(2) 0.55830(18) 0.0326(6) Uani 1 1 d . . . . .
F7 F 0.76607(12) 0.5839(2) 0.60155(18) 0.0346(6) Uani 1 1 d . . . . .
F13 F 0.56293(13) 0.7039(2) 0.86358(18) 0.0377(7) Uani 1 1 d . . . . .
F11 F 0.61192(14) 0.5375(2) 0.7210(2) 0.0411(7) Uani 1 1 d . . . . .
F3 F 1.16418(13) 0.4565(2) 0.22104(19) 0.0401(7) Uani 1 1 d . . . . .
F10 F 0.52780(14) 0.5946(2) 0.62484(19) 0.0421(7) Uani 1 1 d . . . . .
F2 F 1.18767(14) 0.6361(2) 0.2385(2) 0.0496(8) Uani 1 1 d . . . . .
C2 C 0.9726(2) 0.5423(3) 0.2502(3) 0.0199(9) Uani 1 1 d . . . . .
C6 C 0.8190(3) 0.5451(4) 0.2623(3) 0.0250(10) Uani 1 1 d . . . . .
C8 C 0.8757(2) 0.6495(3) 0.4008(3) 0.0196(9) Uani 1 1 d . . . . .
C7 C 0.8871(2) 0.5809(3) 0.3072(3) 0.0190(9) Uani 1 1 d . . . . .
C13 C 1.0931(2) 0.6269(3) 0.4506(3) 0.0221(9) Uani 1 1 d . . . . .
C10 C 0.9302(3) 0.7039(3) 0.5620(3) 0.0222(9) Uani 1 1 d . . . . .
C19 C 0.5771(2) 0.6302(3) 0.6882(3) 0.0272(10) Uani 1 1 d . . . . .
C12 C 1.0771(2) 0.6633(3) 0.5551(3) 0.0233(9) Uani 1 1 d . . . . .
C16 C 0.7904(2) 0.7109(3) 0.4511(3) 0.0218(9) Uani 1 1 d . . . . .
C17 C 0.7244(2) 0.6388(3) 0.5391(3) 0.0244(10) Uani 1 1 d . . . . .
C1 C 1.0419(2) 0.5760(3) 0.2899(3) 0.0187(9) Uani 1 1 d . . . . .
C5 C 0.8340(3) 0.4744(4) 0.1745(4) 0.0322(11) Uani 1 1 d . . . . .
C18 C 0.6499(2) 0.7069(3) 0.6171(3) 0.0240(9) Uani 1 1 d . . . . .
C9 C 0.9425(2) 0.6610(3) 0.4531(3) 0.0169(8) Uani 1 1 d . . . . .
C4 C 0.9157(3) 0.4342(4) 0.1218(3) 0.0280(10) Uani 1 1 d . . . . .
C3 C 0.9829(3) 0.4678(4) 0.1580(3) 0.0254(10) Uani 1 1 d . . . . .
C15 C 1.1318(2) 0.5609(4) 0.2167(3) 0.0266(10) Uani 1 1 d . . . . .
C14 C 1.0275(2) 0.6217(3) 0.3954(3) 0.0186(9) Uani 1 1 d . . . . .
C11 C 0.9948(2) 0.7037(3) 0.6112(3) 0.0244(9) Uani 1 1 d . . . . .
C20 C 0.5186(2) 0.6904(4) 0.7899(3) 0.0276(10) Uani 1 1 d . . . . .
F14 F 0.38081(14) 0.6355(3) 0.7837(2) 0.0509(8) Uani 1 1 d . . . . .
F15 F 0.45361(15) 0.5118(2) 0.8495(2) 0.0533(8) Uani 1 1 d . . . . .
C21 C 0.4345(2) 0.6230(4) 0.8459(3) 0.0299(10) Uani 1 1 d . . . . .
C22 C 0.3857(3) 0.6574(4) 0.9641(4) 0.0370(11) Uani 1 1 d . . . . .
F20 F 0.43362(15) 0.6307(2) 1.0317(2) 0.0512(8) Uani 1 1 d . . . . .
F19 F 0.31481(14) 0.5917(2) 0.9912(2) 0.0504(8) Uani 1 1 d . . . . .
F16 F 0.42387(15) 0.8511(2) 0.9734(2) 0.0484(7) Uani 1 1 d . . . . .
F17 F 0.31222(17) 0.8147(3) 0.9186(3) 0.0634(9) Uani 1 1 d . . . . .
F18 F 0.30793(17) 0.7937(3) 1.0878(2) 0.0631(9) Uani 1 1 d . . . . .
C23 C 0.3573(3) 0.7833(4) 0.9872(4) 0.0447(13) Uani 1 1 d . . . . .
H4 H 0.921(2) 0.380(3) 0.064(3) 0.030(11) Uiso 1 1 d . . . . .
H12 H 1.125(2) 0.661(3) 0.593(3) 0.030(11) Uiso 1 1 d . . . . .
H3 H 1.0358(19) 0.441(3) 0.128(2) 0.001(8) Uiso 1 1 d . . . . .
H6 H 0.762(2) 0.566(3) 0.293(3) 0.006(8) Uiso 1 1 d . . . . .
H10 H 0.876(2) 0.738(3) 0.604(3) 0.029(11) Uiso 1 1 d . . . . .
H13 H 1.150(2) 0.601(3) 0.417(3) 0.028(11) Uiso 1 1 d . . . . .
H11 H 0.983(2) 0.729(3) 0.687(3) 0.035(11) Uiso 1 1 d . . . . .
H5 H 0.793(3) 0.451(4) 0.162(4) 0.047(16) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F5 C16 1.354(4) . y
F9 C18 1.348(4) . y
F4 C16 1.359(4) . y
F12 C20 1.336(4) . y
F1 C15 1.349(4) . y
F6 C17 1.347(4) . y
F8 C18 1.338(4) . y
F7 C17 1.341(4) . y
F13 C20 1.341(4) . y
F11 C19 1.336(4) . y
F3 C15 1.329(5) . y
F10 C19 1.350(4) . y
F2 C15 1.342(4) . y
C2 C7 1.450(5) . y
C2 C1 1.411(5) . y
C2 C3 1.431(5) . y
C6 C7 1.440(5) . y
C6 C5 1.354(6) . y
C8 C7 1.405(5) . y
C8 C16 1.533(5) . y
C8 C9 1.428(5) . y
C13 C12 1.353(5) . y
C13 C14 1.431(5) . y
C10 C9 1.436(5) . y
C10 C11 1.363(5) . y
C19 C18 1.556(5) . y
C19 C20 1.547(6) . y
C12 C11 1.412(6) . y
C16 C17 1.563(5) . y
C17 C18 1.553(5) . y
C1 C15 1.510(5) . y
C1 C14 1.405(5) . y
C5 C4 1.392(6) . y
C9 C14 1.447(5) . y
C4 C3 1.355(6) . y
C20 C21 1.566(6) . y
F14 C21 1.339(5) . y
F15 C21 1.332(5) . y
C21 C22 1.548(6) . y
C22 F20 1.347(5) . y
C22 F19 1.345(5) . y
C22 C23 1.538(6) . y
F16 C23 1.310(5) . y
F17 C23 1.337(5) . y
F18 C23 1.317(5) . y

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
C1 C2 C7 118.9(3) . . y
C1 C2 C3 122.5(3) . . y
C3 C2 C7 118.5(3) . . y
C5 C6 C7 121.4(4) . . y
C7 C8 C16 120.7(3) . . y
C7 C8 C9 120.7(3) . . y
C9 C8 C16 118.5(3) . . y
C6 C7 C2 116.5(3) . . y
C8 C7 C2 119.0(3) . . y
C8 C7 C6 124.5(3) . . y
C12 C13 C14 122.0(4) . . y
C11 C10 C9 121.6(4) . . y
F11 C19 F10 108.2(3) . . y
F11 C19 C18 109.0(3) . . y
F11 C19 C20 108.5(3) . . y
F10 C19 C18 107.9(3) . . y
F10 C19 C20 108.1(3) . . y
C20 C19 C18 114.9(3) . . y
C13 C12 C11 120.0(4) . . y
F5 C16 F4 105.1(3) . . y
F5 C16 C8 110.9(3) . . y
F5 C16 C17 108.0(3) . . y
F4 C16 C8 111.0(3) . . y
F4 C16 C17 107.1(3) . . y
C8 C16 C17 114.4(3) . . y
F6 C17 C16 108.6(3) . . y
F6 C17 C18 107.2(3) . . y
F7 C17 F6 108.4(3) . . y
F7 C17 C16 108.8(3) . . y
F7 C17 C18 107.1(3) . . y
C18 C17 C16 116.4(3) . . y
C2 C1 C15 118.5(3) . . y
C14 C1 C2 120.6(3) . . y
C14 C1 C15 120.9(3) . . y
C6 C5 C4 122.1(4) . . y
F9 C18 C19 108.0(3) . . y
F9 C18 C17 108.5(3) . . y
F8 C18 F9 108.0(3) . . y
F8 C18 C19 108.6(3) . . y
F8 C18 C17 109.1(3) . . y
C17 C18 C19 114.4(3) . . y
C8 C9 C10 124.2(3) . . y
C8 C9 C14 118.3(3) . . y
C10 C9 C14 117.4(3) . . y
C3 C4 C5 119.3(4) . . y
C4 C3 C2 122.1(4) . . y
F1 C15 C1 112.5(3) . . y
F3 C15 F1 106.2(3) . . y
F3 C15 F2 106.7(3) . . y
F3 C15 C1 114.0(3) . . y
F2 C15 F1 103.8(3) . . y
F2 C15 C1 113.0(3) . . y
C13 C14 C9 118.2(3) . . y
C1 C14 C13 122.4(3) . . y
C1 C14 C9 119.3(3) . . y
C10 C11 C12 120.7(4) . . y
F12 C20 F13 108.7(3) . . y
F12 C20 C19 108.8(3) . . y
F12 C20 C21 108.5(3) . . y
F13 C20 C19 108.4(3) . . y
F13 C20 C21 108.0(3) . . y
C19 C20 C21 114.4(3) . . y
F14 C21 C20 107.7(3) . . y
F14 C21 C22 107.8(3) . . y
F15 C21 C20 108.6(3) . . y
F15 C21 F14 108.8(3) . . y
F15 C21 C22 106.2(4) . . y
C22 C21 C20 117.5(3) . . y
F20 C22 C21 109.4(3) . . y
F20 C22 C23 107.0(4) . . y
F19 C22 C21 106.0(3) . . y
F19 C22 F20 108.1(4) . . y
F19 C22 C23 107.5(3) . . y
C23 C22 C21 118.6(4) . . y
F16 C23 C22 110.7(4) . . y
F16 C23 F17 109.2(4) . . y
F16 C23 F18 109.5(4) . . y
F17 C23 C22 108.9(4) . . y
F18 C23 C22 110.2(4) . . y
F18 C23 F17 108.4(4) . . y

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: CHCl3/MeOH'
