# Supplementary Information (SI) for Journal of Materials Chemistry C.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# 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_exp_1_auto_trans
_database_code_depnum_ccdc_archive 'CCDC 2345853'
loop_
_audit_author_name
_audit_author_address
'Shouhei Katao'
;Nara Institute of Science and Technology
Japan
;
_audit_update_record             
;
2024-04-05 deposited with the CCDC.	2024-08-07 downloaded from the CCDC.
;
_audit_creation_date             2024-03-04
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        
1,2-bis(2-methoxy-corannulenyl)perfluorocyclopentene
_chemical_formula_moiety         'C47 H22 F6 O2'
_chemical_formula_sum            'C47 H22 F6 O2'
_chemical_formula_weight         732.64
_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 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'I 1 2/a 1'
_space_group_name_Hall           '-I 2ya'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, z'
'-x+1/2, -y+1/2, -z+1/2'
'x, -y+1/2, z+1/2'

_cell_length_a                   17.5895(3)
_cell_length_b                   7.49120(10)
_cell_length_c                   25.2551(4)
_cell_angle_alpha                90
_cell_angle_beta                 109.857(2)
_cell_angle_gamma                90
_cell_volume                     3129.92(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    15998
_cell_measurement_temperature    103
_cell_measurement_theta_max      74.5850
_cell_measurement_theta_min      3.7130
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.001
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.70198
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.105a (Rigaku Oxford Diffraction, 2024)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.555
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             1496
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.03
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0325
_diffrn_reflns_av_unetI/netI     0.0170
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.966
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            25029
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.966
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.295
_diffrn_reflns_theta_min         3.722
_diffrn_ambient_temperature      103
_diffrn_detector                 'Rigaku HyPix-6000 area detector'
_diffrn_detector_area_resol_mean 10.0
_diffrn_detector_type            'HPC area detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.966
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Rigaku XtaLAB Synergy-R'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  'multi-layer mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'rotating anode X-ray generator'
_diffrn_source_type              PhotonJet-R
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2871
_reflns_number_total             3134
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.820
_refine_diff_density_min         -0.806
_refine_diff_density_rms         0.109
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     263
_refine_ls_number_reflns         3134
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1003
_refine_ls_R_factor_gt           0.0955
_refine_ls_restrained_S_all      1.058
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1207P)²+29.1364P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2653
_refine_ls_wR_factor_ref         0.2690
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Fixed Sof: F3(0.5) F4(0.5) C23(0.5)
3.a Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8), C14(H14), C5(H5), C11(H11), C4(H4), C13(H13), C10(H10)
3.b Idealised Me refined as rotating group:
 C00R(H00A,H00B,H00C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.19438(16) 0.6424(4) 0.59572(12) 0.0317(7) Uani 1 1 d . . . . .
F1 F 0.2652(3) 0.2782(4) 0.59135(17) 0.0789(14) Uani 1 1 d . . . . .
F2 F 0.36960(18) 0.2799(4) 0.5692(2) 0.0852(15) Uani 1 1 d . . . . .
C18 C 0.4371(3) 0.9842(5) 0.69417(17) 0.0275(9) Uani 1 1 d . . . . .
C2 C 0.2675(2) 0.7179(5) 0.60108(16) 0.0247(8) Uani 1 1 d . . . . .
C16 C 0.4165(2) 0.8560(5) 0.60776(15) 0.0277(9) Uani 1 1 d . . . . .
C17 C 0.3772(2) 0.9123(5) 0.64495(16) 0.0261(8) Uani 1 1 d . . . . .
C7 C 0.5043(3) 0.9922(5) 0.79324(17) 0.0299(9) Uani 1 1 d . . . . .
H7 H 0.502822 1.008967 0.830163 0.036 Uiso 1 1 calc R U . . .
C20 C 0.4995(3) 0.8939(5) 0.63255(16) 0.0289(9) Uani 1 1 d . . . . .
C1 C 0.3078(2) 0.6553(5) 0.56501(15) 0.0252(8) Uani 1 1 d . . . . .
C19 C 0.5125(2) 0.9733(5) 0.68569(16) 0.0266(8) Uani 1 1 d . . . . .
C15 C 0.3878(2) 0.7155(5) 0.57054(15) 0.0254(8) Uani 1 1 d . . . . .
C9 C 0.5844(3) 0.9556(6) 0.72990(17) 0.0311(9) Uani 1 1 d . . . . .
C8 C 0.5780(3) 0.9795(5) 0.78568(17) 0.0311(9) Uani 1 1 d . . . . .
H8 H 0.625997 0.986405 0.817579 0.037 Uiso 1 1 calc R U . . .
C6 C 0.4288(2) 0.9809(5) 0.74637(17) 0.0286(9) Uani 1 1 d . . . . .
C21 C 0.2733(2) 0.5028(5) 0.52716(16) 0.0238(8) Uani 1 1 d . . . . .
C3 C 0.3060(2) 0.8398(5) 0.64683(16) 0.0268(8) Uani 1 1 d . . . . .
C14 C 0.4482(3) 0.6340(6) 0.55104(16) 0.0303(9) Uani 1 1 d . . . . .
H14 H 0.431286 0.550516 0.520972 0.036 Uiso 1 1 calc R U . . .
C5 C 0.3509(3) 0.9262(6) 0.74714(17) 0.0310(9) Uani 1 1 d . . . . .
H5 H 0.339323 0.935967 0.781117 0.037 Uiso 1 1 calc R U . . .
C11 C 0.6381(3) 0.8061(6) 0.66390(19) 0.0343(10) Uani 1 1 d . . . . .
H11 H 0.683414 0.759958 0.656018 0.041 Uiso 1 1 calc R U . . .
C22 C 0.2913(2) 0.3143(5) 0.54926(16) 0.0278(9) Uani 1 1 d . . . . .
C12 C 0.5594(3) 0.7977(6) 0.62120(17) 0.0308(9) Uani 1 1 d . . . . .
C4 C 0.2922(3) 0.8594(6) 0.69922(18) 0.0321(9) Uani 1 1 d . . . . .
H4 H 0.241211 0.825721 0.701295 0.038 Uiso 1 1 calc R U . . .
C13 C 0.5297(3) 0.6737(6) 0.57478(17) 0.0323(9) Uani 1 1 d . . . . .
H13 H 0.566952 0.618129 0.560231 0.039 Uiso 1 1 calc R U . . .
C10 C 0.6492(3) 0.8801(6) 0.71643(18) 0.0338(10) Uani 1 1 d . . . . .
H10 H 0.701749 0.880075 0.744038 0.041 Uiso 1 1 calc R U . . .
C00R C 0.1303(3) 0.7709(7) 0.58907(19) 0.0383(11) Uani 1 1 d . . . . .
H00A H 0.123494 0.843780 0.555548 0.057 Uiso 1 1 calc R U . . .
H00B H 0.144364 0.848013 0.622347 0.057 Uiso 1 1 calc R U . . .
H00C H 0.079795 0.707761 0.584810 0.057 Uiso 1 1 calc R U . . .
F3 F 0.1636(3) 0.1637(8) 0.5176(2) 0.0438(13) Uani 0.5 1 d . . P A -1
F4 F 0.257(3) 0.0408(7) 0.498(2) 0.057(6) Uani 0.5 1 d . . P A -1
C23 C 0.2307(5) 0.1958(10) 0.5041(4) 0.0269(18) Uani 0.5 1 d . . P A -1


_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
O1 C2 1.369(5) . ?
O1 C00R 1.447(5) . ?
F1 C22 1.321(5) . ?
F2 C22 1.322(5) . ?
C18 C17 1.434(5) . ?
C18 C19 1.416(6) . ?
C18 C6 1.375(6) . ?
C2 C1 1.411(6) . ?
C2 C3 1.448(5) . ?
C16 C17 1.406(6) . ?
C16 C20 1.410(6) . ?
C16 C15 1.387(5) . ?
C17 C3 1.380(6) . ?
C7 C8 1.376(6) . ?
C7 C6 1.450(6) . ?
C20 C19 1.414(6) . ?
C20 C12 1.384(6) . ?
C1 C15 1.439(6) . ?
C1 C21 1.481(5) . ?
C19 C9 1.379(6) . ?
C15 C14 1.448(6) . ?
C9 C8 1.462(6) . ?
C9 C10 1.414(6) . ?
C6 C5 1.436(6) . ?
C21 C21 1.338(7) 2_556 ?
C21 C22 1.511(5) . ?
C3 C4 1.432(6) . ?
C14 C13 1.385(6) . ?
C5 C4 1.391(6) . ?
C11 C12 1.438(6) . ?
C11 C10 1.389(6) . ?
C22 C23 1.549(9) . ?
C12 C13 1.447(6) . ?
F3 C23 1.356(9) . ?
F4 C23 1.27(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 O1 C00R 113.9(3) . . ?
C19 C18 C17 107.3(3) . . ?
C6 C18 C17 122.6(4) . . ?
C6 C18 C19 123.6(4) . . ?
O1 C2 C1 117.4(3) . . ?
O1 C2 C3 120.6(3) . . ?
C1 C2 C3 121.6(4) . . ?
C17 C16 C20 108.2(3) . . ?
C15 C16 C17 122.2(4) . . ?
C15 C16 C20 122.5(4) . . ?
C16 C17 C18 108.0(3) . . ?
C3 C17 C18 121.8(4) . . ?
C3 C17 C16 124.2(4) . . ?
C8 C7 C6 121.8(4) . . ?
C16 C20 C19 108.4(4) . . ?
C12 C20 C16 123.4(4) . . ?
C12 C20 C19 121.8(4) . . ?
C2 C1 C15 121.5(3) . . ?
C2 C1 C21 119.2(4) . . ?
C15 C1 C21 118.5(3) . . ?
C20 C19 C18 108.1(3) . . ?
C9 C19 C18 122.1(4) . . ?
C9 C19 C20 122.4(4) . . ?
C16 C15 C1 114.9(4) . . ?
C16 C15 C14 114.3(4) . . ?
C1 C15 C14 129.9(4) . . ?
C19 C9 C8 114.8(4) . . ?
C19 C9 C10 115.8(4) . . ?
C10 C9 C8 127.8(4) . . ?
C7 C8 C9 121.8(4) . . ?
C18 C6 C7 114.6(4) . . ?
C18 C6 C5 115.5(4) . . ?
C5 C6 C7 128.2(4) . . ?
C1 C21 C22 119.6(3) . . ?
C21 C21 C1 129.5(2) 2_556 . ?
C21 C21 C22 110.92(19) 2_556 . ?
C17 C3 C2 113.9(4) . . ?
C17 C3 C4 115.6(4) . . ?
C4 C3 C2 128.4(4) . . ?
C13 C14 C15 122.2(4) . . ?
C4 C5 C6 121.4(4) . . ?
C10 C11 C12 121.4(4) . . ?
F1 C22 F2 104.9(4) . . ?
F1 C22 C21 113.7(3) . . ?
F1 C22 C23 97.7(4) . . ?
F2 C22 C21 112.5(3) . . ?
F2 C22 C23 122.4(5) . . ?
C21 C22 C23 105.0(4) . . ?
C20 C12 C11 115.3(4) . . ?
C20 C12 C13 114.3(4) . . ?
C11 C12 C13 128.8(4) . . ?
C5 C4 C3 122.1(4) . . ?
C14 C13 C12 121.6(4) . . ?
C11 C10 C9 121.7(4) . . ?
F3 C23 C22 110.9(6) . . ?
F4 C23 C22 115(2) . . ?
F4 C23 F3 104(2) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Dichloromethane'
