# Electronic Supplementary Material (ESI) for Chemical Communications
# This journal is © The Royal Society of Chemistry 2013

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  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.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_cd21396

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H13 F3 N2 O2'
_chemical_formula_weight         370.32

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'
O O 0.0106 0.0060 '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           Triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.7008(16)
_cell_length_b                   8.9697(17)
_cell_length_c                   14.190(3)
_cell_angle_alpha                74.227(4)
_cell_angle_beta                 80.042(4)
_cell_angle_gamma                67.803(4)
_cell_volume                     870.6(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1438
_cell_measurement_theta_min      5.243
_cell_measurement_theta_max      47.355

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.243
_exptl_crystal_size_mid          0.211
_exptl_crystal_size_min          0.147
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.413
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             380
_exptl_absorpt_coefficient_mu    0.114
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.33069
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5212
_diffrn_reflns_av_R_equivalents  0.0285
_diffrn_reflns_av_sigmaI/netI    0.0500
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.62
_diffrn_reflns_theta_max         26.00
_reflns_number_total             3401
_reflns_number_gt                2292
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F^2^ against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F^2^, conventional R-factors R are based 
 on F, with F set to zero for negative F^2^. The threshold expression of 
 F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F^2^ 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/[\s^2^(Fo^2^)+(0.0894P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/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         3401
_refine_ls_number_parameters     244
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0761
_refine_ls_R_factor_gt           0.0522
_refine_ls_wR_factor_ref         0.1570
_refine_ls_wR_factor_gt          0.1385
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_restrained_S_all      1.012
_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 0.1336(3) 0.9843(2) 0.07006(12) 0.1136(6) Uani 1 1 d . . .
F2 F 0.4186(2) 0.8255(2) 0.09383(11) 0.1046(5) Uani 1 1 d . . .
F3 F 0.3124(3) 0.8773(3) -0.04455(11) 0.1489(8) Uani 1 1 d . . .
N1 N 0.0017(2) 0.70702(18) 0.46084(11) 0.0508(4) Uani 1 1 d . . .
N2 N -0.0072(2) 0.77949(18) 0.52792(11) 0.0519(4) Uani 1 1 d . . .
O1 O 0.13269(19) 0.58471(17) 0.43670(10) 0.0683(4) Uani 1 1 d . . .
O2 O 0.14835(19) 0.83245(19) 0.26242(11) 0.0726(4) Uani 1 1 d . . .
C1 C -0.1637(2) 0.7756(2) 0.40491(13) 0.0490(4) Uani 1 1 d . . .
C2 C -0.3400(3) 0.8177(2) 0.45373(15) 0.0587(5) Uani 1 1 d . . .
H2 H -0.3536 0.8081 0.5213 0.070 Uiso 1 1 calc R . .
C3 C -0.4963(3) 0.8743(3) 0.40114(17) 0.0662(6) Uani 1 1 d . . .
H3 H -0.6161 0.9058 0.4332 0.079 Uiso 1 1 calc R . .
C4 C -0.4757(3) 0.8844(3) 0.30196(17) 0.0681(6) Uani 1 1 d . . .
H4 H -0.5813 0.9216 0.2669 0.082 Uiso 1 1 calc R . .
C5 C -0.2974(3) 0.8393(2) 0.25391(15) 0.0594(5) Uani 1 1 d . . .
H5 H -0.2842 0.8448 0.1868 0.071 Uiso 1 1 calc R . .
C6 C -0.1388(2) 0.7860(2) 0.30471(13) 0.0494(4) Uani 1 1 d . . .
C7 C 0.0499(2) 0.7652(2) 0.24849(13) 0.0510(5) Uani 1 1 d . . .
C8 C 0.1065(3) 0.6625(2) 0.17396(13) 0.0554(5) Uani 1 1 d . . .
C9 C 0.0634(3) 0.5207(3) 0.19741(18) 0.0760(6) Uani 1 1 d . . .
H9 H -0.0066 0.4970 0.2562 0.091 Uiso 1 1 calc R . .
C10 C 0.1215(4) 0.4125(4) 0.1357(2) 0.1024(9) Uani 1 1 d . . .
H10 H 0.0941 0.3156 0.1538 0.123 Uiso 1 1 calc R . .
C11 C 0.2188(4) 0.4482(5) 0.0487(2) 0.1098(10) Uani 1 1 d . . .
H11 H 0.2577 0.3759 0.0069 0.132 Uiso 1 1 calc R . .
C12 C 0.2598(3) 0.5901(4) 0.02231(18) 0.0913(8) Uani 1 1 d . . .
H12 H 0.3238 0.6146 -0.0384 0.110 Uiso 1 1 calc R . .
C13 C 0.2078(3) 0.6986(3) 0.08430(14) 0.0659(6) Uani 1 1 d . . .
C14 C 0.2665(4) 0.8450(4) 0.05184(17) 0.0870(8) Uani 1 1 d . . .
C15 C 0.1415(3) 0.7223(2) 0.58930(12) 0.0498(4) Uani 1 1 d . . .
C16 C 0.1106(3) 0.8211(2) 0.65478(15) 0.0651(6) Uani 1 1 d . . .
H16 H 0.0022 0.9142 0.6529 0.078 Uiso 1 1 calc R . .
C17 C 0.2360(4) 0.7845(3) 0.72189(16) 0.0786(7) Uani 1 1 d . . .
H17 H 0.2125 0.8522 0.7654 0.094 Uiso 1 1 calc R . .
C18 C 0.3975(3) 0.6473(3) 0.72531(16) 0.0734(6) Uani 1 1 d . . .
H18 H 0.4836 0.6222 0.7709 0.088 Uiso 1 1 calc R . .
C19 C 0.4307(3) 0.5480(3) 0.66101(15) 0.0687(6) Uani 1 1 d . . .
H19 H 0.5399 0.4553 0.6634 0.082 Uiso 1 1 calc R . .
C20 C 0.3044(3) 0.5834(2) 0.59286(14) 0.0591(5) Uani 1 1 d . . .
H20 H 0.3281 0.5151 0.5497 0.071 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
F1 0.1071(13) 0.0954(11) 0.1170(13) 0.0112(9) -0.0147(10) -0.0337(10)
F2 0.0709(10) 0.1525(14) 0.1027(11) -0.0195(10) 0.0063(8) -0.0646(10)
F3 0.176(2) 0.209(2) 0.0609(9) 0.0104(10) 0.0157(10) -0.1061(17)
N1 0.0414(8) 0.0521(8) 0.0540(8) -0.0139(7) 0.0035(7) -0.0128(7)
N2 0.0490(9) 0.0526(8) 0.0507(8) -0.0150(7) -0.0006(7) -0.0132(7)
O1 0.0491(8) 0.0715(9) 0.0729(9) -0.0336(7) -0.0034(6) 0.0028(7)
O2 0.0504(8) 0.1071(11) 0.0795(10) -0.0394(9) 0.0113(7) -0.0429(8)
C1 0.0382(9) 0.0500(10) 0.0581(10) -0.0152(8) -0.0008(8) -0.0137(8)
C2 0.0457(11) 0.0637(11) 0.0657(12) -0.0223(9) 0.0101(9) -0.0188(9)
C3 0.0368(10) 0.0757(13) 0.0865(15) -0.0267(11) 0.0097(10) -0.0204(9)
C4 0.0400(11) 0.0790(14) 0.0893(15) -0.0211(12) -0.0093(10) -0.0221(10)
C5 0.0461(11) 0.0746(13) 0.0624(11) -0.0170(10) -0.0022(9) -0.0264(9)
C6 0.0373(9) 0.0568(10) 0.0561(10) -0.0147(8) -0.0006(8) -0.0186(8)
C7 0.0374(9) 0.0638(11) 0.0519(10) -0.0122(9) -0.0023(8) -0.0190(9)
C8 0.0385(10) 0.0748(12) 0.0542(10) -0.0173(9) -0.0005(8) -0.0206(9)
C9 0.0623(14) 0.0878(16) 0.0862(15) -0.0377(13) 0.0173(11) -0.0327(12)
C10 0.0810(18) 0.113(2) 0.138(2) -0.073(2) 0.0227(18) -0.0439(16)
C11 0.0704(18) 0.160(3) 0.123(2) -0.093(2) 0.0176(16) -0.0361(19)
C12 0.0600(15) 0.153(3) 0.0670(14) -0.0474(16) 0.0110(11) -0.0349(16)
C13 0.0447(11) 0.1002(16) 0.0509(11) -0.0198(11) -0.0025(9) -0.0218(11)
C14 0.0744(17) 0.119(2) 0.0583(14) -0.0013(14) 0.0039(12) -0.0404(16)
C15 0.0479(10) 0.0483(10) 0.0490(10) -0.0062(8) -0.0005(8) -0.0169(8)
C16 0.0722(14) 0.0529(11) 0.0643(12) -0.0153(9) -0.0135(10) -0.0105(10)
C17 0.0978(19) 0.0710(14) 0.0717(14) -0.0223(12) -0.0218(13) -0.0238(13)
C18 0.0698(15) 0.0835(15) 0.0671(13) -0.0094(12) -0.0179(11) -0.0268(12)
C19 0.0473(12) 0.0811(14) 0.0685(13) -0.0143(11) -0.0054(10) -0.0136(10)
C20 0.0485(11) 0.0650(12) 0.0579(11) -0.0158(9) 0.0037(9) -0.0155(9)

_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 C14 1.339(3) . ?
F2 C14 1.337(3) . ?
F3 C14 1.332(3) . ?
N1 O1 1.2598(18) . ?
N1 N2 1.270(2) . ?
N1 C1 1.457(2) . ?
N2 C15 1.411(2) . ?
O2 C7 1.200(2) . ?
C1 C2 1.377(2) . ?
C1 C6 1.384(2) . ?
C2 C3 1.381(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.371(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.386(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.384(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.503(2) . ?
C7 C8 1.491(3) . ?
C8 C9 1.376(3) . ?
C8 C13 1.398(3) . ?
C9 C10 1.381(3) . ?
C9 H9 0.9300 . ?
C10 C11 1.354(4) . ?
C10 H10 0.9300 . ?
C11 C12 1.366(4) . ?
C11 H11 0.9300 . ?
C12 C13 1.389(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.479(3) . ?
C15 C16 1.385(2) . ?
C15 C20 1.391(3) . ?
C16 C17 1.362(3) . ?
C16 H16 0.9300 . ?
C17 C18 1.377(3) . ?
C17 H17 0.9300 . ?
C18 C19 1.372(3) . ?
C18 H18 0.9300 . ?
C19 C20 1.381(3) . ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?

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
O1 N1 N2 128.97(16) . . ?
O1 N1 C1 116.15(14) . . ?
N2 N1 C1 114.88(14) . . ?
N1 N2 C15 120.54(14) . . ?
C2 C1 C6 121.74(17) . . ?
C2 C1 N1 119.33(17) . . ?
C6 C1 N1 118.79(15) . . ?
C1 C2 C3 119.19(19) . . ?
C1 C2 H2 120.4 . . ?
C3 C2 H2 120.4 . . ?
C4 C3 C2 120.27(18) . . ?
C4 C3 H3 119.9 . . ?
C2 C3 H3 119.9 . . ?
C3 C4 C5 119.98(19) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
C6 C5 C4 120.74(19) . . ?
C6 C5 H5 119.6 . . ?
C4 C5 H5 119.6 . . ?
C1 C6 C5 118.05(16) . . ?
C1 C6 C7 121.99(15) . . ?
C5 C6 C7 119.37(16) . . ?
O2 C7 C8 121.87(16) . . ?
O2 C7 C6 120.41(16) . . ?
C8 C7 C6 117.70(16) . . ?
C9 C8 C13 118.68(19) . . ?
C9 C8 C7 117.56(18) . . ?
C13 C8 C7 123.70(18) . . ?
C8 C9 C10 121.5(2) . . ?
C8 C9 H9 119.3 . . ?
C10 C9 H9 119.3 . . ?
C11 C10 C9 119.7(3) . . ?
C11 C10 H10 120.2 . . ?
C9 C10 H10 120.2 . . ?
C10 C11 C12 120.2(3) . . ?
C10 C11 H11 119.9 . . ?
C12 C11 H11 119.9 . . ?
C11 C12 C13 121.3(2) . . ?
C11 C12 H12 119.3 . . ?
C13 C12 H12 119.3 . . ?
C12 C13 C8 118.6(2) . . ?
C12 C13 C14 117.6(2) . . ?
C8 C13 C14 123.77(19) . . ?
F3 C14 F2 105.5(2) . . ?
F3 C14 F1 105.8(2) . . ?
F2 C14 F1 106.4(2) . . ?
F3 C14 C13 111.9(2) . . ?
F2 C14 C13 112.7(2) . . ?
F1 C14 C13 113.9(2) . . ?
C16 C15 C20 118.75(18) . . ?
C16 C15 N2 112.25(15) . . ?
C20 C15 N2 128.99(17) . . ?
C17 C16 C15 121.29(19) . . ?
C17 C16 H16 119.4 . . ?
C15 C16 H16 119.4 . . ?
C16 C17 C18 120.0(2) . . ?
C16 C17 H17 120.0 . . ?
C18 C17 H17 120.0 . . ?
C19 C18 C17 119.6(2) . . ?
C19 C18 H18 120.2 . . ?
C17 C18 H18 120.2 . . ?
C18 C19 C20 121.0(2) . . ?
C18 C19 H19 119.5 . . ?
C20 C19 H19 119.5 . . ?
C19 C20 C15 119.41(19) . . ?
C19 C20 H20 120.3 . . ?
C15 C20 H20 120.3 . . ?

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
O1 N1 N2 C15 -1.6(3) . . . . ?
C1 N1 N2 C15 178.17(14) . . . . ?
O1 N1 C1 C2 136.25(18) . . . . ?
N2 N1 C1 C2 -43.5(2) . . . . ?
O1 N1 C1 C6 -39.4(2) . . . . ?
N2 N1 C1 C6 140.86(17) . . . . ?
C6 C1 C2 C3 -1.1(3) . . . . ?
N1 C1 C2 C3 -176.56(16) . . . . ?
C1 C2 C3 C4 1.6(3) . . . . ?
C2 C3 C4 C5 -0.7(3) . . . . ?
C3 C4 C5 C6 -0.9(3) . . . . ?
C2 C1 C6 C5 -0.5(3) . . . . ?
N1 C1 C6 C5 175.03(15) . . . . ?
C2 C1 C6 C7 170.62(17) . . . . ?
N1 C1 C6 C7 -13.9(3) . . . . ?
C4 C5 C6 C1 1.5(3) . . . . ?
C4 C5 C6 C7 -169.85(18) . . . . ?
C1 C6 C7 O2 -44.8(3) . . . . ?
C5 C6 C7 O2 126.2(2) . . . . ?
C1 C6 C7 C8 136.79(18) . . . . ?
C5 C6 C7 C8 -52.2(2) . . . . ?
O2 C7 C8 C9 141.5(2) . . . . ?
C6 C7 C8 C9 -40.1(2) . . . . ?
O2 C7 C8 C13 -35.4(3) . . . . ?
C6 C7 C8 C13 142.98(19) . . . . ?
C13 C8 C9 C10 1.5(3) . . . . ?
C7 C8 C9 C10 -175.6(2) . . . . ?
C8 C9 C10 C11 -1.9(4) . . . . ?
C9 C10 C11 C12 0.3(5) . . . . ?
C10 C11 C12 C13 1.7(5) . . . . ?
C11 C12 C13 C8 -2.0(4) . . . . ?
C11 C12 C13 C14 177.0(3) . . . . ?
C9 C8 C13 C12 0.4(3) . . . . ?
C7 C8 C13 C12 177.28(19) . . . . ?
C9 C8 C13 C14 -178.5(2) . . . . ?
C7 C8 C13 C14 -1.6(3) . . . . ?
C12 C13 C14 F3 18.8(3) . . . . ?
C8 C13 C14 F3 -162.4(2) . . . . ?
C12 C13 C14 F2 -100.0(2) . . . . ?
C8 C13 C14 F2 78.9(3) . . . . ?
C12 C13 C14 F1 138.7(2) . . . . ?
C8 C13 C14 F1 -42.4(3) . . . . ?
N1 N2 C15 C16 177.20(16) . . . . ?
N1 N2 C15 C20 -4.4(3) . . . . ?
C20 C15 C16 C17 -0.1(3) . . . . ?
N2 C15 C16 C17 178.52(19) . . . . ?
C15 C16 C17 C18 0.2(3) . . . . ?
C16 C17 C18 C19 -0.2(3) . . . . ?
C17 C18 C19 C20 0.0(3) . . . . ?
C18 C19 C20 C15 0.2(3) . . . . ?
C16 C15 C20 C19 -0.1(3) . . . . ?
N2 C15 C20 C19 -178.46(17) . . . . ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.228
_refine_diff_density_min         -0.264
_refine_diff_density_rms         0.054
_database_code_depnum_ccdc_archive 'CCDC 950406'