# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_mo_d8v18839_0m
_database_code_depnum_ccdc_archive 'CCDC 1957757'
loop_
_audit_author_name
_audit_author_address
'Jie Sun'
;Shanghai Institute of Organic Chemistry
China
;
_audit_update_record             
;
2019-10-06 deposited with the CCDC.	2019-11-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
1-(1,1,2,2,8,8,8,8,8-Nonafluoro-8λ8-octa-3,5,7-triyn-1-yl)naphthalene
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H7 F9'
_chemical_formula_weight         394.24

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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -y, -z'

_cell_length_a                   7.427(2)
_cell_length_b                   7.782(3)
_cell_length_c                   13.740(5)
_cell_angle_alpha                89.382(10)
_cell_angle_beta                 89.146(10)
_cell_angle_gamma                68.679(10)
_cell_volume                     739.7(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4012
_cell_measurement_theta_min      5.620
_cell_measurement_theta_max      52.213

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.770
_exptl_crystal_F_000             392
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.190
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.182
_shelx_estimated_absorpt_T_min   0.966
_shelx_estimated_absorpt_T_max   0.978
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5257
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8138
_diffrn_reflns_av_unetI/netI     0.0616
_diffrn_reflns_av_R_equivalents  0.0651
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.810
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.008
_diffrn_measured_fraction_theta_full 0.981
_diffrn_reflns_Laue_measured_fraction_max 1.008
_diffrn_reflns_Laue_measured_fraction_full 0.981
_diffrn_reflns_point_group_measured_fraction_max 1.008
_diffrn_reflns_point_group_measured_fraction_full 0.981
_reflns_number_total             2575
_reflns_number_gt                1831
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refined as a 2-component twin. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.24(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2575
_refine_ls_number_parameters     246
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1222
_refine_ls_R_factor_gt           0.0956
_refine_ls_wR_factor_ref         0.3183
_refine_ls_wR_factor_gt          0.2657
_refine_ls_goodness_of_fit_ref   1.231
_refine_ls_restrained_S_all      1.231
_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 0.4753(5) 0.2892(5) 0.8604(3) 0.0798(11) Uani 1 1 d . . . . .
F2 F 0.5315(5) 0.2234(4) 0.7070(3) 0.0721(10) Uani 1 1 d . . . . .
F3 F 0.8817(5) 0.2839(5) 0.7271(4) 0.0917(13) Uani 1 1 d . . . . .
F4 F 0.7889(6) 0.3718(5) 0.8742(3) 0.0959(14) Uani 1 1 d . . . . .
F5 F 0.4799(7) 0.6582(5) 0.9041(3) 0.0899(13) Uani 1 1 d . . . . .
F6 F 0.2671(6) 0.9877(5) 0.8331(3) 0.0949(13) Uani 1 1 d . . . . .
F7 F 0.2613(6) 1.0581(5) 0.6406(3) 0.0943(14) Uani 1 1 d . . . . .
F8 F 0.4777(8) 0.7931(7) 0.5171(3) 0.1047(15) Uani 1 1 d . . . . .
F9 F 0.6902(7) 0.4612(6) 0.5837(3) 0.0935(13) Uani 1 1 d . . . . .
C1 C 0.8618(8) -0.1096(8) 0.7531(4) 0.0585(13) Uani 1 1 d . . . . .
C2 C 0.8645(9) -0.0813(8) 0.6493(4) 0.0669(14) Uani 1 1 d . . . . .
H2 H 0.7929 0.0332 0.6227 0.080 Uiso 1 1 calc R U . . .
C3 C 0.9708(10) -0.2206(9) 0.5904(5) 0.0776(17) Uani 1 1 d . . . . .
H3 H 0.9696 -0.2001 0.5236 0.093 Uiso 1 1 calc R U . . .
C4 C 1.0825(10) -0.3944(9) 0.6271(5) 0.0761(17) Uani 1 1 d . . . . .
H4 H 1.1525 -0.4888 0.5852 0.091 Uiso 1 1 calc R U . . .
C5 C 1.0876(9) -0.4241(8) 0.7252(5) 0.0728(16) Uani 1 1 d . . . . .
H5 H 1.1644 -0.5386 0.7500 0.087 Uiso 1 1 calc R U . . .
C6 C 0.9784(8) -0.2842(8) 0.7894(4) 0.0619(14) Uani 1 1 d . . . . .
C7 C 0.9881(10) -0.3189(8) 0.8925(5) 0.0752(17) Uani 1 1 d . . . . .
H7 H 1.0685 -0.4330 0.9163 0.090 Uiso 1 1 calc R U . . .
C8 C 0.8822(11) -0.1882(9) 0.9550(4) 0.0793(18) Uani 1 1 d . . . . .
H8 H 0.8898 -0.2122 1.0216 0.095 Uiso 1 1 calc R U . . .
C9 C 0.7603(10) -0.0159(9) 0.9202(4) 0.0741(17) Uani 1 1 d . . . . .
H9 H 0.6864 0.0727 0.9641 0.089 Uiso 1 1 calc R U . . .
C10 C 0.7478(8) 0.0251(7) 0.8215(4) 0.0610(14) Uani 1 1 d . . . . .
C11 C 0.6218(8) 0.2171(8) 0.7931(4) 0.0646(14) Uani 1 1 d . . . . .
C12 C 0.7214(9) 0.3587(8) 0.7857(5) 0.0698(15) Uani 1 1 d . . . . .
C13 C 0.6004(8) 0.5461(7) 0.7477(4) 0.0610(14) Uani 1 1 d . . . . .
C14 C 0.4858(9) 0.6855(8) 0.8080(4) 0.0653(14) Uani 1 1 d . . . . .
C15 C 0.3730(9) 0.8561(8) 0.7732(5) 0.0696(16) Uani 1 1 d . . . . .
C16 C 0.3702(9) 0.8944(8) 0.6743(5) 0.0665(14) Uani 1 1 d . . . . .
C17 C 0.4787(9) 0.7577(9) 0.6121(4) 0.0701(16) Uani 1 1 d . . . . .
C18 C 0.5906(9) 0.5880(8) 0.6477(4) 0.0656(15) 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 C11 1.375(7) . ?
F2 C11 1.361(7) . ?
F3 C12 1.372(8) . ?
F4 C12 1.340(8) . ?
F5 C14 1.339(7) . ?
F6 C15 1.326(7) . ?
F7 C16 1.319(7) . ?
F8 C17 1.331(7) . ?
F9 C18 1.328(7) . ?
C1 C6 1.410(8) . ?
C1 C10 1.432(8) . ?
C1 C2 1.442(8) . ?
C2 C3 1.353(9) . ?
C2 H2 0.9300 . ?
C3 C4 1.398(10) . ?
C3 H3 0.9300 . ?
C4 C5 1.363(10) . ?
C4 H4 0.9300 . ?
C5 C6 1.407(9) . ?
C5 H5 0.9300 . ?
C6 C7 1.437(9) . ?
C7 C8 1.344(10) . ?
C7 H7 0.9300 . ?
C8 C9 1.401(10) . ?
C8 H8 0.9300 . ?
C9 C10 1.386(9) . ?
C9 H9 0.9300 . ?
C10 C11 1.497(8) . ?
C11 C12 1.537(9) . ?
C12 C13 1.500(9) . ?
C13 C14 1.383(8) . ?
C13 C18 1.405(9) . ?
C14 C15 1.372(9) . ?
C15 C16 1.388(9) . ?
C16 C17 1.373(9) . ?
C17 C18 1.369(9) . ?

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 C1 C10 117.8(5) . . ?
C6 C1 C2 117.3(5) . . ?
C10 C1 C2 124.9(5) . . ?
C3 C2 C1 120.3(6) . . ?
C3 C2 H2 119.8 . . ?
C1 C2 H2 119.8 . . ?
C2 C3 C4 121.9(6) . . ?
C2 C3 H3 119.1 . . ?
C4 C3 H3 119.1 . . ?
C5 C4 C3 119.3(5) . . ?
C5 C4 H4 120.4 . . ?
C3 C4 H4 120.4 . . ?
C4 C5 C6 121.0(6) . . ?
C4 C5 H5 119.5 . . ?
C6 C5 H5 119.5 . . ?
C5 C6 C1 120.2(6) . . ?
C5 C6 C7 119.8(5) . . ?
C1 C6 C7 120.0(5) . . ?
C8 C7 C6 120.7(5) . . ?
C8 C7 H7 119.7 . . ?
C6 C7 H7 119.7 . . ?
C7 C8 C9 120.2(6) . . ?
C7 C8 H8 119.9 . . ?
C9 C8 H8 119.9 . . ?
C10 C9 C8 121.3(6) . . ?
C10 C9 H9 119.4 . . ?
C8 C9 H9 119.4 . . ?
C9 C10 C1 120.0(5) . . ?
C9 C10 C11 116.6(5) . . ?
C1 C10 C11 123.3(5) . . ?
F2 C11 F1 105.2(4) . . ?
F2 C11 C10 112.6(4) . . ?
F1 C11 C10 110.5(5) . . ?
F2 C11 C12 106.7(5) . . ?
F1 C11 C12 104.9(5) . . ?
C10 C11 C12 116.1(5) . . ?
F4 C12 F3 105.7(5) . . ?
F4 C12 C13 110.5(5) . . ?
F3 C12 C13 109.5(6) . . ?
F4 C12 C11 107.3(6) . . ?
F3 C12 C11 107.2(5) . . ?
C13 C12 C11 116.1(5) . . ?
C14 C13 C18 115.9(5) . . ?
C14 C13 C12 122.4(5) . . ?
C18 C13 C12 121.7(5) . . ?
F5 C14 C15 116.8(5) . . ?
F5 C14 C13 120.7(5) . . ?
C15 C14 C13 122.5(6) . . ?
F6 C15 C14 121.0(6) . . ?
F6 C15 C16 118.8(5) . . ?
C14 C15 C16 120.2(5) . . ?
F7 C16 C17 120.8(6) . . ?
F7 C16 C15 120.3(6) . . ?
C17 C16 C15 118.8(5) . . ?
F8 C17 C18 120.2(6) . . ?
F8 C17 C16 119.4(6) . . ?
C18 C17 C16 120.4(6) . . ?
F9 C18 C17 117.4(5) . . ?
F9 C18 C13 120.4(5) . . ?
C17 C18 C13 122.2(5) . . ?

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
C6 C1 C2 C3 2.1(9) . . . . ?
C10 C1 C2 C3 -177.0(6) . . . . ?
C1 C2 C3 C4 -0.7(10) . . . . ?
C2 C3 C4 C5 -1.2(10) . . . . ?
C3 C4 C5 C6 1.7(10) . . . . ?
C4 C5 C6 C1 -0.3(9) . . . . ?
C4 C5 C6 C7 -179.4(6) . . . . ?
C10 C1 C6 C5 177.5(5) . . . . ?
C2 C1 C6 C5 -1.6(8) . . . . ?
C10 C1 C6 C7 -3.4(8) . . . . ?
C2 C1 C6 C7 177.5(6) . . . . ?
C5 C6 C7 C8 -178.8(6) . . . . ?
C1 C6 C7 C8 2.1(9) . . . . ?
C6 C7 C8 C9 0.1(11) . . . . ?
C7 C8 C9 C10 -0.9(11) . . . . ?
C8 C9 C10 C1 -0.4(10) . . . . ?
C8 C9 C10 C11 -176.5(6) . . . . ?
C6 C1 C10 C9 2.6(8) . . . . ?
C2 C1 C10 C9 -178.4(6) . . . . ?
C6 C1 C10 C11 178.4(5) . . . . ?
C2 C1 C10 C11 -2.6(9) . . . . ?
C9 C10 C11 F2 -145.9(5) . . . . ?
C1 C10 C11 F2 38.1(7) . . . . ?
C9 C10 C11 F1 -28.6(7) . . . . ?
C1 C10 C11 F1 155.4(5) . . . . ?
C9 C10 C11 C12 90.6(7) . . . . ?
C1 C10 C11 C12 -85.3(7) . . . . ?
F2 C11 C12 F4 171.9(4) . . . . ?
F1 C11 C12 F4 60.6(5) . . . . ?
C10 C11 C12 F4 -61.7(6) . . . . ?
F2 C11 C12 F3 -75.0(6) . . . . ?
F1 C11 C12 F3 173.7(5) . . . . ?
C10 C11 C12 F3 51.4(7) . . . . ?
F2 C11 C12 C13 47.7(7) . . . . ?
F1 C11 C12 C13 -63.6(6) . . . . ?
C10 C11 C12 C13 174.1(5) . . . . ?
F4 C12 C13 C14 -34.3(8) . . . . ?
F3 C12 C13 C14 -150.3(6) . . . . ?
C11 C12 C13 C14 88.2(7) . . . . ?
F4 C12 C13 C18 148.3(6) . . . . ?
F3 C12 C13 C18 32.4(8) . . . . ?
C11 C12 C13 C18 -89.1(7) . . . . ?
C18 C13 C14 F5 178.0(5) . . . . ?
C12 C13 C14 F5 0.5(9) . . . . ?
C18 C13 C14 C15 -1.6(9) . . . . ?
C12 C13 C14 C15 -179.1(5) . . . . ?
F5 C14 C15 F6 1.4(9) . . . . ?
C13 C14 C15 F6 -178.9(6) . . . . ?
F5 C14 C15 C16 -179.5(6) . . . . ?
C13 C14 C15 C16 0.1(10) . . . . ?
F6 C15 C16 F7 -1.2(9) . . . . ?
C14 C15 C16 F7 179.7(5) . . . . ?
F6 C15 C16 C17 -179.5(5) . . . . ?
C14 C15 C16 C17 1.4(9) . . . . ?
F7 C16 C17 F8 1.9(9) . . . . ?
C15 C16 C17 F8 -179.8(6) . . . . ?
F7 C16 C17 C18 -179.7(6) . . . . ?
C15 C16 C17 C18 -1.4(9) . . . . ?
F8 C17 C18 F9 -2.4(9) . . . . ?
C16 C17 C18 F9 179.2(5) . . . . ?
F8 C17 C18 C13 178.2(5) . . . . ?
C16 C17 C18 C13 -0.2(9) . . . . ?
C14 C13 C18 F9 -177.7(5) . . . . ?
C12 C13 C18 F9 -0.2(9) . . . . ?
C14 C13 C18 C17 1.6(9) . . . . ?
C12 C13 C18 C17 179.1(6) . . . . ?

_refine_diff_density_max         0.306
_refine_diff_density_min         -0.318
_refine_diff_density_rms         0.082

_shelxl_version_number           2013-4

