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

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#                                CCDC 
# 
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# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
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#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
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#  except for the purpose of generating routine backup copies
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#  data retrieval see:
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data_130704_lxj008_2

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H17 F3 N2'
_chemical_formula_sum            'C23 H17 F3 N2'
_chemical_formula_weight         378.39

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'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           tetragonal
_symmetry_space_group_name_H-M   'P 41'
_symmetry_space_group_name_Hall  'P 4w '

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-y, x, z+1/4'
'-x, -y, z+1/2'
'y, -x, z+3/4'

_cell_length_a                   10.77844(12)
_cell_length_b                   10.77844(12)
_cell_length_c                   16.0189(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1860.99(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    170(2)
_cell_measurement_reflns_used    7199
_cell_measurement_theta_min      4.0981
_cell_measurement_theta_max      67.3925

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.26
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.351
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             784
_exptl_absorpt_coefficient_mu    0.842
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6879
_exptl_absorpt_correction_T_max  0.8107
_exptl_absorpt_process_details   
;
CrysAlis PRO (Agilent Technologies, 2011) 
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      170(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.3592
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            11747
_diffrn_reflns_av_R_equivalents  0.0275
_diffrn_reflns_av_sigmaI/netI    0.0186
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         4.10
_diffrn_reflns_theta_max         67.51
_reflns_number_total             2544
_reflns_number_gt                2484
_reflns_threshold_expression     >2sigma(I)

_computing_cell_refinement       'CrysAlis PRO (Agilent Technologies, 2011)'
_computing_data_collection       'CrysAlis PRO'
_computing_data_reduction        'CrysAlis PRO'
_computing_molecular_graphics    'OLEX2 (Dolomanov et al., 2009)'
_computing_publication_material  OLEX2
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (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)+(0.0409P)²+0.1308P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0018(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 'Flack (1983), 814 Friedel pairs'
_chemical_absolute_configuration ad
_refine_ls_abs_structure_Flack   -0.03(10)
_refine_ls_number_reflns         2544
_refine_ls_number_parameters     262
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0258
_refine_ls_R_factor_gt           0.0249
_refine_ls_wR_factor_ref         0.0657
_refine_ls_wR_factor_gt          0.0643
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_restrained_S_all      1.061
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.25214(10) 0.86414(11) 0.08984(7) 0.0558(3) Uani 1 1 d . . .
F2 F 0.06015(9) 0.87060(10) 0.12503(8) 0.0549(3) Uani 1 1 d . . .
F3 F 0.20123(9) 0.94376(9) 0.20750(8) 0.0478(3) Uani 1 1 d . . .
N1 N 0.52568(11) 0.66343(12) 0.21316(9) 0.0329(3) Uani 1 1 d D . .
H1 H 0.5997(15) 0.6387(19) 0.1928(14) 0.056(6) Uiso 1 1 d D . .
N2 N 0.15124(12) 0.63366(14) 0.12928(9) 0.0390(3) Uani 1 1 d D . .
H2 H 0.0690(14) 0.6369(17) 0.1271(14) 0.045(5) Uiso 1 1 d D . .
C1 C 0.59518(14) 0.73801(13) 0.35287(12) 0.0362(4) Uani 1 1 d . . .
H1A H 0.6800 0.7165 0.3459 0.043 Uiso 1 1 calc R . .
C2 C 0.55320(15) 0.79023(14) 0.42599(12) 0.0388(4) Uani 1 1 d . . .
H2A H 0.6097 0.8043 0.4705 0.047 Uiso 1 1 calc R . .
C3 C 0.42744(15) 0.82306(13) 0.43561(11) 0.0356(3) Uani 1 1 d . . .
H3 H 0.4006 0.8592 0.4866 0.043 Uiso 1 1 calc R . .
C4 C 0.34245(13) 0.80370(12) 0.37230(11) 0.0314(3) Uani 1 1 d . . .
H4 H 0.2582 0.8274 0.3794 0.038 Uiso 1 1 calc R . .
C5 C 0.38174(12) 0.74879(12) 0.29748(10) 0.0284(3) Uani 1 1 d . . .
C6 C 0.50959(13) 0.71777(13) 0.28974(11) 0.0305(3) Uani 1 1 d . . .
C7 C 0.41505(13) 0.65952(14) 0.17170(11) 0.0325(3) Uani 1 1 d . . .
C8 C 0.32397(13) 0.70931(13) 0.22095(10) 0.0294(3) Uani 1 1 d . . .
C10 C 0.19398(14) 0.50862(15) 0.12901(11) 0.0372(4) Uani 1 1 d . . .
C11 C 0.31759(14) 0.48367(16) 0.10706(10) 0.0368(4) Uani 1 1 d . . .
C12 C 0.40191(14) 0.59267(16) 0.09057(11) 0.0384(4) Uani 1 1 d . . .
H12A H 0.4839 0.5638 0.0705 0.046 Uiso 1 1 calc R . .
H12B H 0.3653 0.6480 0.0478 0.046 Uiso 1 1 calc R . .
C13 C 0.35950(16) 0.36278(17) 0.10659(12) 0.0453(4) Uani 1 1 d . . .
H13 H 0.4440 0.3463 0.0940 0.054 Uiso 1 1 calc R . .
C14 C 0.27967(19) 0.26442(18) 0.12432(13) 0.0514(5) Uani 1 1 d . . .
H14 H 0.3096 0.1815 0.1245 0.062 Uiso 1 1 calc R . .
C15 C 0.15739(19) 0.28888(18) 0.14149(13) 0.0525(5) Uani 1 1 d . . .
H15 H 0.1018 0.2222 0.1515 0.063 Uiso 1 1 calc R . .
C16 C 0.11427(16) 0.40959(18) 0.14432(12) 0.0479(4) Uani 1 1 d . . .
H16 H 0.0295 0.4251 0.1568 0.057 Uiso 1 1 calc R . .
C17 C 0.18860(13) 0.72266(14) 0.19623(10) 0.0320(3) Uani 1 1 d . . .
C18 C 0.10416(13) 0.70826(14) 0.27282(10) 0.0323(3) Uani 1 1 d . . .
C19 C 0.11258(14) 0.59734(15) 0.31720(10) 0.0359(4) Uani 1 1 d . . .
H19 H 0.1707 0.5364 0.2997 0.043 Uiso 1 1 calc R . .
C20 C 0.03899(15) 0.57346(19) 0.38576(12) 0.0459(4) Uani 1 1 d . . .
H20 H 0.0458 0.4966 0.4144 0.055 Uiso 1 1 calc R . .
C21 C -0.04537(16) 0.6627(2) 0.41285(13) 0.0518(5) Uani 1 1 d . . .
H21 H -0.0960 0.6477 0.4604 0.062 Uiso 1 1 calc R . .
C22 C -0.05438(15) 0.77286(19) 0.36985(14) 0.0505(5) Uani 1 1 d . . .
H22 H -0.1116 0.8341 0.3883 0.061 Uiso 1 1 calc R . .
C23 C 0.01828(14) 0.79649(16) 0.30012(12) 0.0405(4) Uani 1 1 d . . .
H23 H 0.0096 0.8727 0.2709 0.049 Uiso 1 1 calc R . .
C24 C 0.17548(15) 0.85048(16) 0.15448(12) 0.0418(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 C24 1.333(2) . ?
F2 C24 1.347(2) . ?
F3 C24 1.345(2) . ?
N1 C7 1.366(2) . ?
N1 C6 1.370(2) . ?
N1 H1 0.903(16) . ?
N2 C10 1.424(2) . ?
N2 C17 1.494(2) . ?
N2 H2 0.888(14) . ?
C1 C2 1.376(3) . ?
C1 C6 1.386(2) . ?
C1 H1A 0.9500 . ?
C2 C3 1.409(2) . ?
C2 H2A 0.9500 . ?
C3 C4 1.383(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.402(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.4234(19) . ?
C5 C8 1.439(2) . ?
C7 C8 1.369(2) . ?
C7 C12 1.493(2) . ?
C8 C17 1.5187(19) . ?
C10 C16 1.392(2) . ?
C10 C11 1.404(2) . ?
C11 C13 1.379(2) . ?
C11 C12 1.509(2) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.395(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.372(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.382(3) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 C18 1.535(2) . ?
C17 C24 1.538(2) . ?
C18 C19 1.394(2) . ?
C18 C23 1.397(2) . ?
C19 C20 1.379(2) . ?
C19 H19 0.9500 . ?
C20 C21 1.393(3) . ?
C20 H20 0.9500 . ?
C21 C22 1.376(3) . ?
C21 H21 0.9500 . ?
C22 C23 1.388(3) . ?
C22 H22 0.9500 . ?
C23 H23 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
C7 N1 C6 109.76(13) . . ?
C7 N1 H1 126.0(14) . . ?
C6 N1 H1 124.2(14) . . ?
C10 N2 C17 121.50(13) . . ?
C10 N2 H2 111.1(12) . . ?
C17 N2 H2 105.8(14) . . ?
C2 C1 C6 117.81(14) . . ?
C2 C1 H1A 121.1 . . ?
C6 C1 H1A 121.1 . . ?
C1 C2 C3 120.80(15) . . ?
C1 C2 H2A 119.6 . . ?
C3 C2 H2A 119.6 . . ?
C4 C3 C2 121.27(16) . . ?
C4 C3 H3 119.4 . . ?
C2 C3 H3 119.4 . . ?
C3 C4 C5 119.38(14) . . ?
C3 C4 H4 120.3 . . ?
C5 C4 H4 120.3 . . ?
C4 C5 C6 117.77(14) . . ?
C4 C5 C8 136.23(13) . . ?
C6 C5 C8 105.98(13) . . ?
N1 C6 C1 129.51(14) . . ?
N1 C6 C5 107.51(13) . . ?
C1 C6 C5 122.94(15) . . ?
N1 C7 C8 109.50(14) . . ?
N1 C7 C12 121.41(14) . . ?
C8 C7 C12 128.53(13) . . ?
C7 C8 C5 107.25(12) . . ?
C7 C8 C17 125.15(14) . . ?
C5 C8 C17 127.57(13) . . ?
C16 C10 C11 118.88(16) . . ?
C16 C10 N2 121.70(15) . . ?
C11 C10 N2 119.27(15) . . ?
C13 C11 C10 119.55(15) . . ?
C13 C11 C12 122.51(15) . . ?
C10 C11 C12 117.80(15) . . ?
C7 C12 C11 106.30(13) . . ?
C7 C12 H12A 110.5 . . ?
C11 C12 H12A 110.5 . . ?
C7 C12 H12B 110.5 . . ?
C11 C12 H12B 110.5 . . ?
H12A C12 H12B 108.7 . . ?
C11 C13 C14 121.00(17) . . ?
C11 C13 H13 119.5 . . ?
C14 C13 H13 119.5 . . ?
C15 C14 C13 119.17(18) . . ?
C15 C14 H14 120.4 . . ?
C13 C14 H14 120.4 . . ?
C14 C15 C16 120.69(17) . . ?
C14 C15 H15 119.7 . . ?
C16 C15 H15 119.7 . . ?
C15 C16 C10 120.56(16) . . ?
C15 C16 H16 119.7 . . ?
C10 C16 H16 119.7 . . ?
N2 C17 C8 112.66(12) . . ?
N2 C17 C18 110.42(12) . . ?
C8 C17 C18 110.58(13) . . ?
N2 C17 C24 103.79(13) . . ?
C8 C17 C24 106.65(12) . . ?
C18 C17 C24 112.55(12) . . ?
C19 C18 C23 117.85(16) . . ?
C19 C18 C17 117.10(13) . . ?
C23 C18 C17 125.03(15) . . ?
C20 C19 C18 121.93(16) . . ?
C20 C19 H19 119.0 . . ?
C18 C19 H19 119.0 . . ?
C19 C20 C21 119.64(19) . . ?
C19 C20 H20 120.2 . . ?
C21 C20 H20 120.2 . . ?
C22 C21 C20 119.08(18) . . ?
C22 C21 H21 120.5 . . ?
C20 C21 H21 120.5 . . ?
C21 C22 C23 121.43(16) . . ?
C21 C22 H22 119.3 . . ?
C23 C22 H22 119.3 . . ?
C22 C23 C18 120.06(17) . . ?
C22 C23 H23 120.0 . . ?
C18 C23 H23 120.0 . . ?
F1 C24 F3 106.26(14) . . ?
F1 C24 F2 106.39(15) . . ?
F3 C24 F2 106.93(14) . . ?
F1 C24 C17 112.32(14) . . ?
F3 C24 C17 112.09(15) . . ?
F2 C24 C17 112.42(13) . . ?

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        67.51
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         0.130
_refine_diff_density_min         -0.121
_refine_diff_density_rms         0.026
_database_code_depnum_ccdc_archive 'CCDC 953552'
