# Electronic Supplementary Material (ESI) for Organic .
# This journal is © The Royal Society of Chemistry 2014


data_a

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H9 F6 N3'
_chemical_formula_sum            'C18 H9 F6 N3'
_chemical_formula_weight         381.28

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'
N N 0.0061 0.0033 '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   P2(1)/c

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                   14.868(4)
_cell_length_b                   9.506(3)
_cell_length_c                   11.977(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 111.598(3)
_cell_angle_gamma                90.00
_cell_volume                     1574.0(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    1.47
_cell_measurement_theta_min      27.48
_cell_measurement_theta_max      1537

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.19
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.609
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             768
_exptl_absorpt_coefficient_mu    0.148
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6469
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2007)'


_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Saturn724+ CCD'
_diffrn_measurement_method       'ω scans at fixed χ = 45°'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10544
_diffrn_reflns_av_R_equivalents  0.0365
_diffrn_reflns_av_sigmaI/netI    0.0304
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         2.60
_diffrn_reflns_theta_max         27.49
_reflns_number_total             3570
_reflns_number_gt                3166
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2007)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'Olex2 ver 1.1'
_computing_molecular_graphics    'Olex2 ver 1.1'
_computing_publication_material  'SHELX97 (Sheldrick, 2008)'


_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)+(0.0648P)²+0.4939P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3570
_refine_ls_number_parameters     272
_refine_ls_number_restraints     36
_refine_ls_R_factor_all          0.0627
_refine_ls_R_factor_gt           0.0554
_refine_ls_wR_factor_ref         0.1472
_refine_ls_wR_factor_gt          0.1412
_refine_ls_goodness_of_fit_ref   1.140
_refine_ls_restrained_S_all      1.159
_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 0.79152(10) 0.77843(13) 0.68024(10) 0.0534(3) Uani 1 1 d . . .
F2 F 0.87570(9) 0.86957(13) 0.58730(11) 0.0532(3) Uani 1 1 d . . .
F3 F 0.72513(10) 0.91730(12) 0.53095(12) 0.0586(4) Uani 1 1 d . . .
F4 F 0.5042(2) 0.6726(3) 0.2079(3) 0.0773(14) Uani 0.678(8) 1 d PU A 1
F4A F 0.4924(4) 0.5736(14) 0.2298(5) 0.100(5) Uani 0.322(8) 1 d PU A 2
F5 F 0.57597(18) 0.5812(7) 0.10502(19) 0.097(2) Uani 0.678(8) 1 d PU A 1
F5A F 0.5575(5) 0.6800(7) 0.1315(7) 0.083(3) Uani 0.322(8) 1 d PU A 2
F6 F 0.5161(2) 0.4553(3) 0.2044(3) 0.0784(16) Uani 0.678(8) 1 d PU A 1
F6A F 0.5592(4) 0.4619(6) 0.1326(6) 0.078(3) Uani 0.322(8) 1 d PU A 2
N1 N 0.71613(10) 0.46671(14) 0.32600(12) 0.0297(3) Uani 1 1 d . . .
N2 N 0.85678(10) 0.34701(15) 0.43792(12) 0.0304(3) Uani 1 1 d . . .
N3 N 0.97721(12) 0.20265(18) 0.54633(15) 0.0457(4) Uani 1 1 d . . .
C1 C 0.65873(12) 0.57747(17) 0.31169(15) 0.0306(4) Uani 1 1 d . A .
C2 C 0.67984(12) 0.69267(18) 0.38805(15) 0.0334(4) Uani 1 1 d . . .
H2 H 0.6369 0.7704 0.3732 0.040 Uiso 1 1 calc R . .
C3 C 0.76543(13) 0.69042(18) 0.48626(15) 0.0328(4) Uani 1 1 d . . .
C4 C 0.82824(12) 0.57429(18) 0.50877(15) 0.0312(4) Uani 1 1 d . . .
C5 C 0.91559(14) 0.5574(2) 0.61349(16) 0.0382(4) Uani 1 1 d . . .
H5 H 0.9367 0.6307 0.6713 0.046 Uiso 1 1 calc R . .
C6 C 0.96687(14) 0.4376(2) 0.62882(16) 0.0407(4) Uani 1 1 d . . .
H6 H 1.0235 0.4264 0.6987 0.049 Uiso 1 1 calc R . .
C7 C 0.93822(12) 0.32814(19) 0.54295(16) 0.0364(4) Uani 1 1 d . . .
C8 C 0.91994(14) 0.1388(2) 0.44141(18) 0.0431(4) Uani 1 1 d . . .
H8 H 0.9310 0.0464 0.4192 0.052 Uiso 1 1 calc R . .
C9 C 0.79826(11) 0.46567(17) 0.42189(14) 0.0283(3) Uani 1 1 d . . .
C10 C 0.84542(13) 0.22207(18) 0.37237(16) 0.0344(4) Uani 1 1 d . . .
C11 C 0.76975(12) 0.18923(18) 0.25510(15) 0.0333(4) Uani 1 1 d . . .
C12 C 0.75351(14) 0.27206(19) 0.15361(16) 0.0382(4) Uani 1 1 d . . .
H12 H 0.7922 0.3532 0.1589 0.046 Uiso 1 1 calc R . .
C13 C 0.68180(15) 0.2375(2) 0.04525(17) 0.0448(5) Uani 1 1 d . . .
H13 H 0.6705 0.2959 -0.0229 0.054 Uiso 1 1 calc R . .
C14 C 0.62674(15) 0.1183(2) 0.03595(19) 0.0484(5) Uani 1 1 d . . .
H14 H 0.5767 0.0954 -0.0382 0.058 Uiso 1 1 calc R . .
C15 C 0.64437(16) 0.0321(2) 0.1347(2) 0.0506(5) Uani 1 1 d . . .
H15 H 0.6077 -0.0515 0.1277 0.061 Uiso 1 1 calc R . .
C16 C 0.71559(15) 0.0675(2) 0.24408(18) 0.0427(4) Uani 1 1 d . . .
H16 H 0.7273 0.0081 0.3117 0.051 Uiso 1 1 calc R . .
C17 C 0.56492(13) 0.57083(19) 0.20419(16) 0.0383(4) Uani 1 1 d . . .
C23 C 0.78926(14) 0.8137(2) 0.57084(17) 0.0404(4) 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 1.341(2) . ?
F2 C23 1.337(2) . ?
F3 C23 1.331(2) . ?
F4 C17 1.335(3) . ?
F4A C17 1.225(5) . ?
F5 C17 1.261(3) . ?
F5A C17 1.333(5) . ?
F6 C17 1.317(3) . ?
F6A C17 1.327(5) . ?
N1 C1 1.326(2) . ?
N1 C9 1.333(2) . ?
N2 C9 1.394(2) . ?
N2 C10 1.399(2) . ?
N2 C7 1.400(2) . ?
N3 C7 1.320(2) . ?
N3 C8 1.373(3) . ?
C1 C2 1.387(2) . ?
C1 C17 1.512(2) . ?
C2 C3 1.379(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.407(2) . ?
C3 C23 1.503(2) . ?
C4 C9 1.416(2) . ?
C4 C5 1.444(2) . ?
C5 C6 1.345(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.414(3) . ?
C6 H6 0.9500 . ?
C8 C10 1.365(2) . ?
C8 H8 0.9500 . ?
C10 C11 1.474(2) . ?
C11 C16 1.388(3) . ?
C11 C12 1.393(2) . ?
C12 C13 1.382(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.378(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.382(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.389(3) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?

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 N1 C9 117.32(14) . . ?
C9 N2 C10 132.01(14) . . ?
C9 N2 C7 121.14(14) . . ?
C10 N2 C7 106.34(14) . . ?
C7 N3 C8 104.72(15) . . ?
N1 C1 C2 124.27(15) . . ?
N1 C1 C17 115.16(14) . . ?
C2 C1 C17 120.57(15) . . ?
C3 C2 C1 117.65(15) . . ?
C3 C2 H2 121.2 . . ?
C1 C2 H2 121.2 . . ?
C2 C3 C4 120.99(15) . . ?
C2 C3 C23 118.51(16) . . ?
C4 C3 C23 120.49(16) . . ?
C3 C4 C9 115.10(15) . . ?
C3 C4 C5 125.09(16) . . ?
C9 C4 C5 119.76(16) . . ?
C6 C5 C4 119.72(17) . . ?
C6 C5 H5 120.1 . . ?
C4 C5 H5 120.1 . . ?
C5 C6 C7 121.34(17) . . ?
C5 C6 H6 119.3 . . ?
C7 C6 H6 119.3 . . ?
N3 C7 N2 111.60(16) . . ?
N3 C7 C6 129.15(17) . . ?
N2 C7 C6 119.24(16) . . ?
C10 C8 N3 112.93(17) . . ?
C10 C8 H8 123.5 . . ?
N3 C8 H8 123.5 . . ?
N1 C9 N2 116.87(14) . . ?
N1 C9 C4 124.63(15) . . ?
N2 C9 C4 118.49(15) . . ?
C8 C10 N2 104.41(16) . . ?
C8 C10 C11 128.24(17) . . ?
N2 C10 C11 127.35(14) . . ?
C16 C11 C12 118.70(17) . . ?
C16 C11 C10 118.68(16) . . ?
C12 C11 C10 122.56(16) . . ?
C13 C12 C11 120.73(18) . . ?
C13 C12 H12 119.6 . . ?
C11 C12 H12 119.6 . . ?
C14 C13 C12 120.10(19) . . ?
C14 C13 H13 119.9 . . ?
C12 C13 H13 119.9 . . ?
C13 C14 C15 119.88(19) . . ?
C13 C14 H14 120.1 . . ?
C15 C14 H14 120.1 . . ?
C14 C15 C16 120.1(2) . . ?
C14 C15 H15 119.9 . . ?
C16 C15 H15 119.9 . . ?
C11 C16 C15 120.39(19) . . ?
C11 C16 H16 119.8 . . ?
C15 C16 H16 119.8 . . ?
F4A C17 F5 131.7(3) . . ?
F4A C17 F6 58.7(6) . . ?
F5 C17 F6 109.3(3) . . ?
F4A C17 F6A 109.0(6) . . ?
F5 C17 F6A 56.8(4) . . ?
F6 C17 F6A 56.4(4) . . ?
F4A C17 F5A 106.1(6) . . ?
F5 C17 F5A 48.1(4) . . ?
F6 C17 F5A 137.5(3) . . ?
F6A C17 F5A 102.4(5) . . ?
F4A C17 F4 46.2(5) . . ?
F5 C17 F4 107.4(3) . . ?
F6 C17 F4 103.0(3) . . ?
F6A C17 F4 134.7(3) . . ?
F5A C17 F4 64.1(4) . . ?
F4A C17 C1 114.0(3) . . ?
F5 C17 C1 113.55(19) . . ?
F6 C17 C1 111.69(17) . . ?
F6A C17 C1 113.7(2) . . ?
F5A C17 C1 110.6(3) . . ?
F4 C17 C1 111.41(18) . . ?
F3 C23 F2 106.34(16) . . ?
F3 C23 F1 107.02(16) . . ?
F2 C23 F1 106.16(15) . . ?
F3 C23 C3 112.02(15) . . ?
F2 C23 C3 112.61(16) . . ?
F1 C23 C3 112.26(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
C9 N1 C1 C2 1.6(2) . . . . ?
C9 N1 C1 C17 -177.80(15) . . . . ?
N1 C1 C2 C3 -1.1(3) . . . . ?
C17 C1 C2 C3 178.27(16) . . . . ?
C1 C2 C3 C4 -0.9(3) . . . . ?
C1 C2 C3 C23 -179.42(16) . . . . ?
C2 C3 C4 C9 2.1(2) . . . . ?
C23 C3 C4 C9 -179.37(15) . . . . ?
C2 C3 C4 C5 -175.14(17) . . . . ?
C23 C3 C4 C5 3.4(3) . . . . ?
C3 C4 C5 C6 175.94(18) . . . . ?
C9 C4 C5 C6 -1.2(3) . . . . ?
C4 C5 C6 C7 1.4(3) . . . . ?
C8 N3 C7 N2 0.0(2) . . . . ?
C8 N3 C7 C6 179.0(2) . . . . ?
C9 N2 C7 N3 172.84(16) . . . . ?
C10 N2 C7 N3 0.2(2) . . . . ?
C9 N2 C7 C6 -6.3(3) . . . . ?
C10 N2 C7 C6 -178.96(17) . . . . ?
C5 C6 C7 N3 -176.7(2) . . . . ?
C5 C6 C7 N2 2.3(3) . . . . ?
C7 N3 C8 C10 -0.2(2) . . . . ?
C1 N1 C9 N2 178.26(14) . . . . ?
C1 N1 C9 C4 -0.1(2) . . . . ?
C10 N2 C9 N1 -1.6(3) . . . . ?
C7 N2 C9 N1 -172.12(15) . . . . ?
C10 N2 C9 C4 176.89(17) . . . . ?
C7 N2 C9 C4 6.4(2) . . . . ?
C3 C4 C9 N1 -1.7(2) . . . . ?
C5 C4 C9 N1 175.76(16) . . . . ?
C3 C4 C9 N2 179.96(14) . . . . ?
C5 C4 C9 N2 -2.6(2) . . . . ?
N3 C8 C10 N2 0.3(2) . . . . ?
N3 C8 C10 C11 -179.80(18) . . . . ?
C9 N2 C10 C8 -171.82(17) . . . . ?
C7 N2 C10 C8 -0.28(19) . . . . ?
C9 N2 C10 C11 8.3(3) . . . . ?
C7 N2 C10 C11 179.82(17) . . . . ?
C8 C10 C11 C16 53.5(3) . . . . ?
N2 C10 C11 C16 -126.6(2) . . . . ?
C8 C10 C11 C12 -123.4(2) . . . . ?
N2 C10 C11 C12 56.5(3) . . . . ?
C16 C11 C12 C13 3.0(3) . . . . ?
C10 C11 C12 C13 179.95(17) . . . . ?
C11 C12 C13 C14 -1.4(3) . . . . ?
C12 C13 C14 C15 -1.1(3) . . . . ?
C13 C14 C15 C16 1.8(3) . . . . ?
C12 C11 C16 C15 -2.2(3) . . . . ?
C10 C11 C16 C15 -179.27(18) . . . . ?
C14 C15 C16 C11 -0.2(3) . . . . ?
N1 C1 C17 F4A 118.6(7) . . . . ?
C2 C1 C17 F4A -60.9(7) . . . . ?
N1 C1 C17 F5 -69.8(4) . . . . ?
C2 C1 C17 F5 110.8(4) . . . . ?
N1 C1 C17 F6 54.3(3) . . . . ?
C2 C1 C17 F6 -125.1(3) . . . . ?
N1 C1 C17 F6A -7.3(5) . . . . ?
C2 C1 C17 F6A 173.3(5) . . . . ?
N1 C1 C17 F5A -121.9(5) . . . . ?
C2 C1 C17 F5A 58.7(6) . . . . ?
N1 C1 C17 F4 168.8(3) . . . . ?
C2 C1 C17 F4 -10.6(3) . . . . ?
C2 C3 C23 F3 -5.7(2) . . . . ?
C4 C3 C23 F3 175.73(16) . . . . ?
C2 C3 C23 F2 -125.54(18) . . . . ?
C4 C3 C23 F2 55.9(2) . . . . ?
C2 C3 C23 F1 114.72(19) . . . . ?
C4 C3 C23 F1 -63.8(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.988
_diffrn_reflns_theta_full        27.49
_diffrn_measured_fraction_theta_full 0.988
_refine_diff_density_max         0.298
_refine_diff_density_min         -0.254
_refine_diff_density_rms         0.061
_database_code_depnum_ccdc_archive 'CCDC 975880'
