# Electronic Supplementary Material (ESI) for Materials Horizons.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_F6TCNNQ
_database_code_depnum_ccdc_archive 'CCDC 1859755'
_audit_update_record             
;
2018-08-01 deposited with the CCDC.
2018-09-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 F6 N4'
_chemical_formula_sum            'C16 F6 N4'
_chemical_formula_weight         362.20

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'
N N 0.0311 0.0180 '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'

_space_group_crystal_system      trigonal
_space_group_IT_number           148
_space_group_name_H-M_alt        'R -3 :H'
_space_group_name_Hall           '-R 3'

_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'
'-y, x-y, z'
'-x+y, -x, z'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'-x+2/3, -y+1/3, -z+1/3'
'y+2/3, -x+y+1/3, -z+1/3'
'x-y+2/3, x+1/3, -z+1/3'
'-x+1/3, -y+2/3, -z+2/3'
'y+1/3, -x+y+2/3, -z+2/3'
'x-y+1/3, x+2/3, -z+2/3'

_cell_length_a                   17.533(4)
_cell_length_b                   17.533(4)
_cell_length_c                   11.484(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     3057.3(16)
_cell_formula_units_Z            9
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    1154
_cell_measurement_theta_min      4.7510
_cell_measurement_theta_max      69.6600

_exptl_crystal_description       rhombohedral
_exptl_crystal_colour            'metallic dark green'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.771
_exptl_crystal_F_000             1602
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    1.507
_shelx_estimated_absorpt_T_min   0.864
_shelx_estimated_absorpt_T_max   0.942
_exptl_absorpt_correction_T_min  0.59439
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'sealed X-ray tube'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            EosS2
_diffrn_detector_area_resol_mean 8.1150
_diffrn_reflns_number            5752
_diffrn_reflns_av_unetI/netI     0.0287
_diffrn_reflns_av_R_equivalents  0.0394
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         4.828
_diffrn_reflns_theta_max         70.510
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             1300
_reflns_number_gt                1005
_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       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_structure_solution    
; 
 SIR97- Altomare A., Burla M.C., Camalli M., Cascarano G.L., Giacovazzo C. , 
 Guagliardi A., Moliterni A.G.G., Polidori G.,Spagna R. 
 (1999) J. Appl. Cryst. 32, 115-119
;
_computing_structure_refinement  
;SHELXL-2018/3 (Sheldrick, 2018)
 Sheldrick GM (2008) Acta Crystallogr A64:112--122 and 
 C. B. Hübschle, G. M. Sheldrick and B. Dittrich
 ShelXle: a Qt graphical user interface for SHELXL
 J. Appl. Cryst., 44, (2011) 1281-1284.
;
_computing_molecular_graphics    
'ORTEP3 for Windows - Farrugia, L. J. J. Appl. Crystallogr. 1997, 30, 565'

_computing_publication_material  
;
 'SHELXL-2018 (Sheldrick, 2018)
;
_refine_special_details          
;
the crystal was weakly diffracting at high angles and
the entire molecule is disordered over two sites in the ratio 78:22.
Atoms of the minor part were refined with ADP restraints.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1070P)²+1.9608P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   .
_refine_ls_hydrogen_treatment    undef
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.00049(18)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         1300
_refine_ls_number_parameters     219
_refine_ls_number_restraints     66
_refine_ls_R_factor_all          0.0729
_refine_ls_R_factor_gt           0.0585
_refine_ls_wR_factor_ref         0.1808
_refine_ls_wR_factor_gt          0.1643
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_restrained_S_all      1.045
_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
C1 C 0.6158(10) 0.4570(9) 0.5281(15) 0.054(3) Uani 0.780(8) 1 d . . P A 1
C2 C 0.5495(2) 0.4310(2) 0.4534(3) 0.0464(11) Uani 0.780(8) 1 d . . P A 1
C3 C 0.4912(4) 0.4670(3) 0.4557(4) 0.0452(13) Uani 0.780(8) 1 d . . P A 1
C4 C 0.4224(3) 0.4428(3) 0.3815(4) 0.0491(11) Uani 0.780(8) 1 d . . P A 1
C5 C 0.3633(4) 0.4779(4) 0.3829(5) 0.0480(13) Uani 0.780(8) 1 d . . P A 1
C7 C 0.2656(8) 0.3833(6) 0.2238(12) 0.060(2) Uani 0.780(8) 1 d . . P A 1
C8 C 0.2421(7) 0.4950(7) 0.3000(10) 0.055(2) Uani 0.780(8) 1 d . . P A 1
N1 N 0.2340(8) 0.3214(9) 0.1621(12) 0.083(3) Uani 0.780(8) 1 d . . P A 1
N2 N 0.1977(5) 0.5213(6) 0.2830(7) 0.0695(18) Uani 0.780(8) 1 d . . P A 1
F1 F 0.6679(2) 0.42190(16) 0.5202(2) 0.0561(8) Uani 0.780(8) 1 d . . P A 1
F3 F 0.4068(3) 0.3834(3) 0.2974(4) 0.0581(13) Uani 0.780(8) 1 d . . P A 1
C1A C 0.5928(12) 0.4885(14) 0.5513(17) 0.063(5) Uani 0.220(8) 1 d . U P A 2
C2A C 0.5199(12) 0.4713(13) 0.4846(15) 0.047(6) Uani 0.220(8) 1 d . U P A 2
C3A C 0.4830(8) 0.4131(8) 0.3928(11) 0.048(4) Uani 0.220(8) 1 d . U P A 2
C4A C 0.4138(14) 0.4032(19) 0.334(2) 0.044(5) Uani 0.220(8) 1 d . U P A 2
C5A C 0.3720(13) 0.4543(13) 0.3629(19) 0.046(5) Uani 0.220(8) 1 d . U P A 2
C7A C 0.251(2) 0.361(2) 0.232(3) 0.039(5) Uani 0.220(8) 1 d . U P A 2
C8A C 0.262(2) 0.491(3) 0.300(4) 0.051(8) Uani 0.220(8) 1 d . U P A 2
F1A F 0.6287(18) 0.4401(16) 0.524(3) 0.055(6) Uani 0.220(8) 1 d . U P A 2
F3A F 0.3803(8) 0.3431(9) 0.2470(11) 0.070(3) Uani 0.220(8) 1 d . U P A 2
N1A N 0.209(3) 0.319(3) 0.165(4) 0.076(9) Uani 0.220(8) 1 d . U P A 2
N2A N 0.2251(19) 0.540(2) 0.304(3) 0.067(7) Uani 0.220(8) 1 d . U P A 2
C6 C 0.2960(2) 0.4507(2) 0.3054(2) 0.0560(7) Uani 1 1 d . . . . .
F2 F 0.53287(12) 0.36953(11) 0.37208(14) 0.0602(6) 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
C1 C2 1.329(16) . ?
C1 F1 1.336(11) . ?
C1 C5 1.436(14) 10_666 ?
C2 F2 1.344(4) . ?
C2 C3 1.445(6) . ?
C3 C4 1.360(8) . ?
C3 C3 1.452(10) 10_666 ?
C4 F3 1.345(5) . ?
C4 C5 1.447(6) . ?
C5 C6 1.359(7) . ?
C7 N1 1.178(17) . ?
C7 C6 1.389(13) . ?
C8 N2 1.104(15) . ?
C8 C6 1.494(10) . ?
C1A C5A 1.32(3) 10_666 ?
C1A F1A 1.32(2) . ?
C1A C2A 1.39(3) . ?
C2A C3A 1.38(2) . ?
C2A C2A 1.53(4) 10_666 ?
C3A C4A 1.32(3) . ?
C3A F2 1.440(11) . ?
C4A F3A 1.35(3) . ?
C4A C5A 1.45(3) . ?
C5A C6 1.46(2) . ?
C7A N1A 1.06(6) . ?
C7A C6 1.60(4) . ?
C8A C6 1.13(3) . ?
C8A N2A 1.31(5) . ?

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 F1 118.7(11) . . ?
C2 C1 C5 124.4(9) . 10_666 ?
F1 C1 C5 116.9(11) . 10_666 ?
C1 C2 F2 121.7(6) . . ?
C1 C2 C3 121.8(6) . . ?
F2 C2 C3 116.5(3) . . ?
C4 C3 C2 124.2(5) . . ?
C4 C3 C3 119.3(6) . 10_666 ?
C2 C3 C3 116.5(6) . 10_666 ?
F3 C4 C3 119.8(5) . . ?
F3 C4 C5 115.2(5) . . ?
C3 C4 C5 125.0(5) . . ?
C6 C5 C1 125.2(7) . 10_666 ?
C6 C5 C4 121.6(5) . . ?
C1 C5 C4 113.1(7) 10_666 . ?
N1 C7 C6 173.7(12) . . ?
N2 C8 C6 170.7(10) . . ?
C5A C1A F1A 118(3) 10_666 . ?
C5A C1A C2A 127(2) 10_666 . ?
F1A C1A C2A 114(2) . . ?
C3A C2A C1A 129(2) . . ?
C4A C3A C2A 123.3(19) . . ?
C4A C3A F2 127.3(17) . . ?
C2A C3A F2 109.4(12) . . ?
C3A C4A F3A 120(2) . . ?
C3A C4A C5A 121(3) . . ?
F3A C4A C5A 120(2) . . ?
C1A C5A C4A 117(2) 10_666 . ?
C1A C5A C6 116.1(17) 10_666 . ?
C4A C5A C6 126.9(18) . . ?
N1A C7A C6 154(4) . . ?
C6 C8A N2A 174(5) . . ?
C5 C6 C7 129.6(7) . . ?
C8A C6 C5A 139(2) . . ?
C5 C6 C8 120.5(5) . . ?
C7 C6 C8 109.9(7) . . ?
C8A C6 C7A 115(3) . . ?
C5A C6 C7A 106.0(16) . . ?

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
F1 C1 C2 F2 1.2(18) . . . . ?
C5 C1 C2 F2 -179.8(9) 10_666 . . . ?
F1 C1 C2 C3 -179.1(9) . . . . ?
C5 C1 C2 C3 -0.1(18) 10_666 . . . ?
C1 C2 C3 C4 -180.0(9) . . . . ?
F2 C2 C3 C4 -0.3(6) . . . . ?
C1 C2 C3 C3 -0.2(11) . . . 10_666 ?
F2 C2 C3 C3 179.5(5) . . . 10_666 ?
C2 C3 C4 F3 -1.8(7) . . . . ?
C3 C3 C4 F3 178.4(5) 10_666 . . . ?
C2 C3 C4 C5 179.7(4) . . . . ?
C3 C3 C4 C5 -0.1(8) 10_666 . . . ?
F3 C4 C5 C6 1.2(7) . . . . ?
C3 C4 C5 C6 179.8(4) . . . . ?
F3 C4 C5 C1 -178.2(8) . . . 10_666 ?
C3 C4 C5 C1 0.3(10) . . . 10_666 ?
C5A C1A C2A C3A 178.4(17) 10_666 . . . ?
F1A C1A C2A C3A -2(3) . . . . ?
C5A C1A C2A C2A 2(3) 10_666 . . 10_666 ?
F1A C1A C2A C2A -179(2) . . . 10_666 ?
C1A C2A C3A C4A -178.7(17) . . . . ?
C2A C2A C3A C4A -2(3) 10_666 . . . ?
C1A C2A C3A F2 0(2) . . . . ?
C2A C2A C3A F2 176.1(15) 10_666 . . . ?
C2A C3A C4A F3A -178.2(15) . . . . ?
F2 C3A C4A F3A 4(3) . . . . ?
C2A C3A C4A C5A 0(3) . . . . ?
F2 C3A C4A C5A -178.0(13) . . . . ?
C3A C4A C5A C1A 1(3) . . . 10_666 ?
F3A C4A C5A C1A 179.6(16) . . . 10_666 ?
C3A C4A C5A C6 179.7(14) . . . . ?
F3A C4A C5A C6 -2(3) . . . . ?
C1 C5 C6 C7 -173.5(10) 10_666 . . . ?
C4 C5 C6 C7 7.1(10) . . . . ?
C1 C5 C6 C8 6.3(12) 10_666 . . . ?
C4 C5 C6 C8 -173.1(6) . . . . ?
C1A C5A C6 C8A 14(4) 10_666 . . . ?
C4A C5A C6 C8A -164(3) . . . . ?
C1A C5A C6 C7A -165.0(19) 10_666 . . . ?
C4A C5A C6 C7A 17(2) . . . . ?
N1A C7A C6 C8A 19(10) . . . . ?
N1A C7A C6 C5A -161(9) . . . . ?

_refine_diff_density_max         0.197
_refine_diff_density_min         -0.290
_refine_diff_density_rms         0.056


_exptl_crystal_recrystallization_method 'Vapour deposition'
