# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2021

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

data_D20013
_database_code_depnum_ccdc_archive 'CCDC 2059168'
loop_
_audit_author_name
_audit_author_address
'Jonathan Becker'
;Justus Liebig University Giessen
Germany
;
_audit_update_record             
;
2021-01-27 deposited with the CCDC.	2021-05-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        2-pentafluorophenylindene
_chemical_name_common            2
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H7 F5'
_chemical_formula_weight         282.21

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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. 
;

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

_cell_length_a                   6.7868(3)
_cell_length_b                   24.2929(10)
_cell_length_c                   6.8686(3)
_cell_angle_alpha                90
_cell_angle_beta                 102.298(2)
_cell_angle_gamma                90
_cell_volume                     1106.45(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9652
_cell_measurement_theta_min      3.15
_cell_measurement_theta_max      36.45

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.694
_exptl_crystal_F_000             568
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.365
_exptl_crystal_size_mid          0.163
_exptl_crystal_size_min          0.055
_exptl_absorpt_coefficient_mu    0.157
_shelx_estimated_absorpt_T_min   0.945
_shelx_estimated_absorpt_T_max   0.991
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6796
_exptl_absorpt_correction_T_max  0.7473
_exptl_absorpt_process_details   'SADABS 2016/2(Sheldrick, 2016)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   
'I\mS micro-focus sealed tube, multilayer optics'
_diffrn_measurement_device_type  'Bruker PHOTON100'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 10.4167
_diffrn_reflns_number            137261
_diffrn_reflns_av_unetI/netI     0.0177
_diffrn_reflns_av_R_equivalents  0.0640
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -36
_diffrn_reflns_limit_k_max       36
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         1.677
_diffrn_reflns_theta_max         32.574
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4026
_reflns_number_gt                3107
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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. 
;

_computing_data_collection       'APEX3 v2019.1-0 (Bruker-AXS, 2017)'
_computing_cell_refinement       'SAINT 8.40A (Bruker-AXS, 2017)'
_computing_data_reduction        'SAINT 8.40A (Bruker-AXS, 2017)'
_computing_structure_solution    'SHELXT-2015 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
; 
 Bruker D8 Venture Dual I\mS fixed chi instrument. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0620P)²+0.2771P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.0131(19)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4026
_refine_ls_number_parameters     345
_refine_ls_number_restraints     1033
_refine_ls_R_factor_all          0.0563
_refine_ls_R_factor_gt           0.0381
_refine_ls_wR_factor_ref         0.1118
_refine_ls_wR_factor_gt          0.0980
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_restrained_S_all      0.966
_refine_ls_shift/su_max          0.000
_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_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 0.8211(14) 0.4271(4) 0.8683(13) 0.0177(10) Uani 0.485(10) 1 d D U P A 1
F2 F 0.7372(9) 0.3210(3) 0.8570(8) 0.0180(11) Uani 0.485(10) 1 d D U P A 1
F3 F 0.3546(7) 0.2821(2) 0.7324(8) 0.0158(10) Uani 0.485(10) 1 d D U P A 1
F4 F 0.0455(8) 0.3546(3) 0.6207(8) 0.0186(11) Uani 0.485(10) 1 d D U P A 1
F5 F 0.1242(16) 0.4611(5) 0.634(2) 0.0243(13) Uani 0.485(10) 1 d D U P A 1
C1 C 0.508(4) 0.5109(4) 0.750(7) 0.0149(2) Uani 0.485(10) 1 d D U P A 1
C2 C 0.3767(15) 0.5542(4) 0.7081(15) 0.0182(14) Uani 0.485(10) 1 d D U P A 1
H2 H 0.234370 0.550788 0.668015 0.022 Uiso 0.485(10) 1 calc R U P A 1
C3 C 0.4856(17) 0.6061(4) 0.733(3) 0.0145(13) Uani 0.485(10) 1 d D U P A 1
C4 C 0.4040(14) 0.6634(4) 0.7028(19) 0.0185(15) Uani 0.485(10) 1 d D U P A 1
H4 H 0.263404 0.670212 0.661919 0.022 Uiso 0.485(10) 1 calc R U P A 1
C5 C 0.530(2) 0.7021(5) 0.734(3) 0.0198(17) Uani 0.485(10) 1 d D U P A 1
H5 H 0.481879 0.738841 0.712541 0.024 Uiso 0.485(10) 1 calc R U P A 1
C6 C 0.736(2) 0.6937(4) 0.797(2) 0.0204(18) Uani 0.485(10) 1 d D U P A 1
H6 H 0.825462 0.724148 0.825910 0.024 Uiso 0.485(10) 1 calc R U P A 1
C7 C 0.8170(18) 0.6355(4) 0.821(3) 0.0161(13) Uani 0.485(10) 1 d D U P A 1
H7 H 0.958123 0.628992 0.855149 0.019 Uiso 0.485(10) 1 calc R U P A 1
C8 C 0.6907(16) 0.5946(4) 0.792(2) 0.0141(12) Uani 0.485(10) 1 d D U P A 1
C9 C 0.7203(12) 0.5335(3) 0.8113(12) 0.0110(9) Uani 0.485(10) 1 d D U P A 1
H9A H 0.782707 0.523004 0.950041 0.013 Uiso 0.485(10) 1 calc R U P A 1
H9AB H 0.806255 0.519986 0.721609 0.013 Uiso 0.485(10) 1 calc R U P A 1
C10 C 0.4753(11) 0.4507(2) 0.7479(15) 0.0120(13) Uani 0.485(10) 1 d D U P A 1
C11 C 0.6283(11) 0.4130(2) 0.8079(14) 0.0090(9) Uani 0.485(10) 1 d D U P A 1
C12 C 0.5879(18) 0.3567(4) 0.796(7) 0.0176(9) Uani 0.485(10) 1 d D U P A 1
C13 C 0.3954(18) 0.3357(4) 0.740(7) 0.0176(4) Uani 0.485(10) 1 d D U P A 1
C14 C 0.2382(13) 0.3717(3) 0.682(3) 0.0175(15) Uani 0.485(10) 1 d D U P A 1
C15 C 0.2853(13) 0.4267(3) 0.6900(17) 0.0221(16) Uani 0.485(10) 1 d D U P A 1
F1A F 0.8055(14) 0.4281(5) 0.8613(15) 0.0290(16) Uani 0.515(10) 1 d D U P A 2
F2A F 0.7370(11) 0.3212(3) 0.8514(11) 0.0370(17) Uani 0.515(10) 1 d D U P A 2
F3A F 0.3519(10) 0.2832(3) 0.7303(11) 0.0356(16) Uani 0.515(10) 1 d D U P A 2
F4A F 0.0449(11) 0.3571(4) 0.6216(11) 0.0351(16) Uani 0.515(10) 1 d D U P A 2
F5A F 0.1060(16) 0.4644(4) 0.6246(17) 0.0211(9) Uani 0.515(10) 1 d D U P A 2
C1A C 0.511(4) 0.5117(4) 0.752(7) 0.0149(2) Uani 0.515(10) 1 d D U P A 2
C2A C 0.6942(13) 0.5379(3) 0.7975(13) 0.0183(13) Uani 0.515(10) 1 d D U P A 2
H2A H 0.821668 0.520152 0.831109 0.022 Uiso 0.515(10) 1 calc R U P A 2
C3A C 0.6627(15) 0.5972(3) 0.7861(19) 0.0131(11) Uani 0.515(10) 1 d D U P A 2
C4A C 0.8160(16) 0.6417(4) 0.830(2) 0.0191(14) Uani 0.515(10) 1 d D U P A 2
H4A H 0.954916 0.633357 0.874920 0.023 Uiso 0.515(10) 1 calc R U P A 2
C5A C 0.7563(19) 0.6912(4) 0.805(2) 0.0183(13) Uani 0.515(10) 1 d D U P A 2
H5A H 0.853186 0.720020 0.823937 0.022 Uiso 0.515(10) 1 calc R U P A 2
C6A C 0.552(2) 0.7043(5) 0.750(3) 0.0173(13) Uani 0.515(10) 1 d D U P A 2
H6A H 0.509427 0.741717 0.738572 0.021 Uiso 0.515(10) 1 calc R U P A 2
C7A C 0.3985(14) 0.6587(4) 0.7091(17) 0.0185(14) Uani 0.515(10) 1 d D U P A 2
H7A H 0.258903 0.667048 0.669939 0.022 Uiso 0.515(10) 1 calc R U P A 2
C8A C 0.4578(16) 0.6077(4) 0.728(3) 0.0130(11) Uani 0.515(10) 1 d D U P A 2
C9A C 0.3458(13) 0.5539(3) 0.6998(13) 0.0122(9) Uani 0.515(10) 1 d D U P A 2
H9AA H 0.270706 0.549414 0.560416 0.015 Uiso 0.515(10) 1 calc R U P A 2
H9AC H 0.250101 0.551175 0.789921 0.015 Uiso 0.515(10) 1 calc R U P A 2
C10A C 0.4625(11) 0.4529(3) 0.7453(15) 0.0162(14) Uani 0.515(10) 1 d D U P A 2
C11A C 0.6110(13) 0.4114(3) 0.7950(17) 0.0222(16) Uani 0.515(10) 1 d D U P A 2
C12A C 0.5801(17) 0.3557(4) 0.801(7) 0.0176(9) Uani 0.515(10) 1 d D U P A 2
C13A C 0.3847(17) 0.3375(4) 0.734(6) 0.0176(4) Uani 0.515(10) 1 d D U P A 2
C14A C 0.2323(12) 0.3760(3) 0.680(3) 0.0174(14) Uani 0.515(10) 1 d D U P A 2
C15A C 0.2665(10) 0.4318(3) 0.6840(12) 0.0085(7) Uani 0.515(10) 1 d D U P A 2


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C11 1.330(8) . ?
F2 C12 1.333(9) . ?
F3 C13 1.330(9) . ?
F4 C14 1.350(8) . ?
F5 C15 1.365(9) . ?
C1 C2 1.37(2) . ?
C1 C10 1.478(8) . ?
C1 C9 1.51(2) . ?
C2 C3 1.454(12) . ?
C2 H2 0.9500 . ?
C3 C8 1.393(9) . ?
C3 C4 1.495(14) . ?
C4 C5 1.259(18) . ?
C4 H4 0.9500 . ?
C5 C6 1.390(9) . ?
C5 H5 0.9500 . ?
C6 C7 1.512(17) . ?
C6 H6 0.9500 . ?
C7 C8 1.301(15) . ?
C7 H7 0.9500 . ?
C8 C9 1.500(11) . ?
C9 H9A 0.9900 . ?
C9 H9AB 0.9900 . ?
C10 C11 1.379(7) . ?
C10 C15 1.393(8) . ?
C11 C12 1.394(8) . ?
C12 C13 1.379(9) . ?
C13 C14 1.371(9) . ?
C14 C15 1.374(8) . ?
F1A C11A 1.363(9) . ?
F2A C12A 1.343(9) . ?
F3A C13A 1.337(8) . ?
F4A C14A 1.331(8) . ?
F5A C15A 1.338(8) . ?
C1A C2A 1.37(2) . ?
C1A C10A 1.463(8) . ?
C1A C9A 1.51(2) . ?
C2A C3A 1.456(10) . ?
C2A H2A 0.9500 . ?
C3A C8A 1.386(8) . ?
C3A C4A 1.487(14) . ?
C4A C5A 1.268(17) . ?
C4A H4A 0.9500 . ?
C5A C6A 1.397(9) . ?
C5A H5A 0.9500 . ?
C6A C7A 1.505(16) . ?
C6A H6A 0.9500 . ?
C7A C8A 1.300(14) . ?
C7A H7A 0.9500 . ?
C8A C9A 1.504(11) . ?
C9A H9AA 0.9900 . ?
C9A H9AC 0.9900 . ?
C10A C15A 1.404(7) . ?
C10A C11A 1.416(8) . ?
C11A C12A 1.369(9) . ?
C12A C13A 1.380(9) . ?
C13A C14A 1.385(8) . ?
C14A C15A 1.375(7) . ?

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 C10 131.8(19) . . ?
C2 C1 C9 108.5(7) . . ?
C10 C1 C9 119.7(17) . . ?
C1 C2 C3 110.5(11) . . ?
C1 C2 H2 124.8 . . ?
C3 C2 H2 124.8 . . ?
C8 C3 C2 108.1(10) . . ?
C8 C3 C4 123.1(10) . . ?
C2 C3 C4 128.8(9) . . ?
C5 C4 C3 117.0(11) . . ?
C5 C4 H4 121.5 . . ?
C3 C4 H4 121.5 . . ?
C4 C5 C6 123.0(13) . . ?
C4 C5 H5 118.5 . . ?
C6 C5 H5 118.5 . . ?
C5 C6 C7 119.3(11) . . ?
C5 C6 H6 120.3 . . ?
C7 C6 H6 120.3 . . ?
C8 C7 C6 119.1(11) . . ?
C8 C7 H7 120.4 . . ?
C6 C7 H7 120.4 . . ?
C7 C8 C3 118.3(11) . . ?
C7 C8 C9 132.3(10) . . ?
C3 C8 C9 109.4(9) . . ?
C8 C9 C1 103.5(9) . . ?
C8 C9 H9A 111.1 . . ?
C1 C9 H9A 111.1 . . ?
C8 C9 H9AB 111.1 . . ?
C1 C9 H9AB 111.1 . . ?
H9A C9 H9AB 109.0 . . ?
C11 C10 C15 113.6(6) . . ?
C11 C10 C1 123.4(11) . . ?
C15 C10 C1 123.0(12) . . ?
F1 C11 C10 123.3(7) . . ?
F1 C11 C12 116.1(7) . . ?
C10 C11 C12 120.5(7) . . ?
F2 C12 C13 117.3(8) . . ?
F2 C12 C11 119.6(8) . . ?
C13 C12 C11 122.9(8) . . ?
F3 C13 C14 118.1(8) . . ?
F3 C13 C12 123.4(8) . . ?
C14 C13 C12 118.5(8) . . ?
F4 C14 C13 122.5(7) . . ?
F4 C14 C15 120.9(8) . . ?
C13 C14 C15 116.7(7) . . ?
F5 C15 C14 114.7(8) . . ?
F5 C15 C10 117.6(8) . . ?
C14 C15 C10 127.7(7) . . ?
C2A C1A C10A 130.4(18) . . ?
C2A C1A C9A 109.3(6) . . ?
C10A C1A C9A 120.3(16) . . ?
C1A C2A C3A 109.4(10) . . ?
C1A C2A H2A 125.3 . . ?
C3A C2A H2A 125.3 . . ?
C8A C3A C2A 108.9(9) . . ?
C8A C3A C4A 122.7(9) . . ?
C2A C3A C4A 128.4(9) . . ?
C5A C4A C3A 118.2(11) . . ?
C5A C4A H4A 120.9 . . ?
C3A C4A H4A 120.9 . . ?
C4A C5A C6A 121.6(12) . . ?
C4A C5A H5A 119.2 . . ?
C6A C5A H5A 119.2 . . ?
C5A C6A C7A 119.3(11) . . ?
C5A C6A H6A 120.4 . . ?
C7A C6A H6A 120.4 . . ?
C8A C7A C6A 119.8(10) . . ?
C8A C7A H7A 120.1 . . ?
C6A C7A H7A 120.1 . . ?
C7A C8A C3A 118.3(10) . . ?
C7A C8A C9A 132.7(9) . . ?
C3A C8A C9A 109.0(9) . . ?
C8A C9A C1A 103.3(9) . . ?
C8A C9A H9AA 111.1 . . ?
C1A C9A H9AA 111.1 . . ?
C8A C9A H9AC 111.1 . . ?
C1A C9A H9AC 111.1 . . ?
H9AA C9A H9AC 109.1 . . ?
C15A C10A C11A 113.0(6) . . ?
C15A C10A C1A 124.0(11) . . ?
C11A C10A C1A 122.9(11) . . ?
F1A C11A C12A 115.3(8) . . ?
F1A C11A C10A 117.2(8) . . ?
C12A C11A C10A 127.2(7) . . ?
F2A C12A C11A 120.5(8) . . ?
F2A C12A C13A 122.5(8) . . ?
C11A C12A C13A 116.7(8) . . ?
F3A C13A C12A 117.9(8) . . ?
F3A C13A C14A 123.3(8) . . ?
C12A C13A C14A 118.8(7) . . ?
F4A C14A C15A 119.5(7) . . ?
F4A C14A C13A 117.4(7) . . ?
C15A C14A C13A 123.2(7) . . ?
F5A C15A C14A 117.0(7) . . ?
F5A C15A C10A 122.2(7) . . ?
C14A C15A C10A 120.8(6) . . ?

_refine_diff_density_max         0.332
_refine_diff_density_min         -0.283
_refine_diff_density_rms         0.059


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
