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

#######################################################################
#
#                 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_shelxl

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H12 F N O2'
_chemical_formula_weight         245.25

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'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/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                   17.7553(6)
_cell_length_b                   4.9562(2)
_cell_length_c                   13.1145(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 95.520(2)
_cell_angle_gamma                90.00
_cell_volume                     1148.71(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.04
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.418
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             512
_exptl_absorpt_coefficient_mu    0.886
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8860
_exptl_absorpt_correction_T_max  0.9654
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'INCOATEC Imus micro-focus source'
_diffrn_measurement_device_type  'Bruker D8 Venture PHOTON 100 CMOS'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13588
_diffrn_reflns_av_R_equivalents  0.0670
_diffrn_reflns_av_sigmaI/netI    0.0385
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         5.00
_diffrn_reflns_theta_max         66.52
_reflns_number_total             2003
_reflns_number_gt                1664
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2 (Bruker, 2010)'
_computing_cell_refinement       'APEX2 (Bruker, 2010); SAINT (Bruker, 2009)'
_computing_data_reduction        'SAINT (Bruker, 2009);XPREP(Sheldrick,2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008); OLEX2 (2009)'
_computing_molecular_graphics    ?
_computing_publication_material  'APEX2 (Bruker, 2010)'
_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)+(0.0396P)²+0.5095P] 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     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2003
_refine_ls_number_parameters     168
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0475
_refine_ls_R_factor_gt           0.0358
_refine_ls_wR_factor_ref         0.0907
_refine_ls_wR_factor_gt          0.0844
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_restrained_S_all      1.031
_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 0.59192(5) 0.6389(2) 0.44330(7) 0.0288(3) Uani 1 1 d . . .
O1 O 0.94033(6) 0.9331(2) 0.09886(8) 0.0202(3) Uani 1 1 d . . .
O2 O 0.75618(6) 1.3920(2) 0.44886(8) 0.0205(3) Uani 1 1 d . . .
N1 N 0.71401(7) 0.9588(3) 0.45146(10) 0.0164(3) Uani 1 1 d . . .
C1 C 0.92045(10) 0.7281(3) 0.02432(12) 0.0217(4) Uani 1 1 d . . .
H1A H 0.9209 0.5517 0.0582 0.033 Uiso 1 1 calc R . .
H1B H 0.9571 0.7279 -0.0270 0.033 Uiso 1 1 calc R . .
H1C H 0.8697 0.7642 -0.0093 0.033 Uiso 1 1 calc R . .
C2 C 0.89300(8) 0.9692(3) 0.17419(11) 0.0163(3) Uani 1 1 d . . .
C3 C 0.82813(9) 0.8181(3) 0.18347(11) 0.0168(3) Uani 1 1 d . . .
H3 H 0.8140 0.6779 0.1360 0.020 Uiso 1 1 calc R . .
C4 C 0.78406(9) 0.8741(3) 0.26284(12) 0.0166(3) Uani 1 1 d . . .
H4 H 0.7401 0.7692 0.2700 0.020 Uiso 1 1 calc R . .
C5 C 0.80329(9) 1.0815(3) 0.33190(12) 0.0153(3) Uani 1 1 d . . .
C6 C 0.75618(8) 1.1601(3) 0.41542(11) 0.0151(3) Uani 1 1 d . . .
C7 C 0.66375(8) 0.9826(3) 0.52886(12) 0.0154(3) Uani 1 1 d . . .
C8 C 0.60222(9) 0.8105(3) 0.52425(12) 0.0191(4) Uani 1 1 d . . .
C9 C 0.55168(9) 0.8066(3) 0.59739(13) 0.0240(4) Uani 1 1 d . . .
H9 H 0.5102 0.6845 0.5921 0.029 Uiso 1 1 calc R . .
C10 C 0.56252(10) 0.9844(3) 0.67887(13) 0.0231(4) Uani 1 1 d . . .
H10 H 0.5284 0.9852 0.7304 0.028 Uiso 1 1 calc R . .
C11 C 0.86918(9) 1.2297(3) 0.32170(12) 0.0184(3) Uani 1 1 d . . .
H11 H 0.8832 1.3711 0.3686 0.022 Uiso 1 1 calc R . .
C12 C 0.91395(9) 1.1727(3) 0.24416(12) 0.0187(4) Uani 1 1 d . . .
H12 H 0.9591 1.2723 0.2386 0.022 Uiso 1 1 calc R . .
C13 C 0.67389(9) 1.1609(3) 0.61081(12) 0.0189(4) Uani 1 1 d . . .
H13 H 0.7154 1.2825 0.6161 0.023 Uiso 1 1 calc R . .
C14 C 0.62301(9) 1.1606(3) 0.68522(12) 0.0214(4) Uani 1 1 d . . .
H14 H 0.6300 1.2832 0.7410 0.026 Uiso 1 1 calc R . .
H1 H 0.7208(10) 0.793(4) 0.4284(14) 0.023(5) Uiso 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 C8 1.3588(18) . ?
O1 C2 1.3690(18) . ?
O1 C1 1.4304(19) . ?
O2 C6 1.2300(18) . ?
N1 C6 1.359(2) . ?
N1 C7 1.419(2) . ?
N1 H1 0.89(2) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 C3 1.389(2) . ?
C2 C12 1.390(2) . ?
C3 C4 1.389(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.391(2) . ?
C4 H4 0.9500 . ?
C5 C11 1.399(2) . ?
C5 C6 1.492(2) . ?
C7 C8 1.383(2) . ?
C7 C13 1.389(2) . ?
C8 C9 1.375(2) . ?
C9 C10 1.384(2) . ?
C9 H9 0.9500 . ?
C10 C14 1.381(2) . ?
C10 H10 0.9500 . ?
C11 C12 1.379(2) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C13 C14 1.392(2) . ?
C13 H13 0.9500 . ?
C14 H14 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
C2 O1 C1 117.24(12) . . ?
C6 N1 C7 126.35(13) . . ?
C6 N1 H1 117.5(12) . . ?
C7 N1 H1 115.9(12) . . ?
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O1 C2 C3 124.38(14) . . ?
O1 C2 C12 115.29(13) . . ?
C3 C2 C12 120.33(14) . . ?
C2 C3 C4 119.31(14) . . ?
C2 C3 H3 120.3 . . ?
C4 C3 H3 120.3 . . ?
C3 C4 C5 121.01(15) . . ?
C3 C4 H4 119.5 . . ?
C5 C4 H4 119.5 . . ?
C4 C5 C11 118.75(14) . . ?
C4 C5 C6 123.44(14) . . ?
C11 C5 C6 117.79(14) . . ?
O2 C6 N1 122.89(14) . . ?
O2 C6 C5 121.65(13) . . ?
N1 C6 C5 115.46(13) . . ?
C8 C7 C13 117.98(14) . . ?
C8 C7 N1 117.75(14) . . ?
C13 C7 N1 124.23(14) . . ?
F1 C8 C9 119.22(14) . . ?
F1 C8 C7 117.82(14) . . ?
C9 C8 C7 122.96(15) . . ?
C8 C9 C10 118.54(15) . . ?
C8 C9 H9 120.7 . . ?
C10 C9 H9 120.7 . . ?
C14 C10 C9 119.93(15) . . ?
C14 C10 H10 120.0 . . ?
C9 C10 H10 120.0 . . ?
C12 C11 C5 120.65(14) . . ?
C12 C11 H11 119.7 . . ?
C5 C11 H11 119.7 . . ?
C11 C12 C2 119.93(14) . . ?
C11 C12 H12 120.0 . . ?
C2 C12 H12 120.0 . . ?
C7 C13 C14 119.81(15) . . ?
C7 C13 H13 120.1 . . ?
C14 C13 H13 120.1 . . ?
C10 C14 C13 120.78(15) . . ?
C10 C14 H14 119.6 . . ?
C13 C14 H14 119.6 . . ?

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
C1 O1 C2 C3 1.0(2) . . . . ?
C1 O1 C2 C12 -179.21(13) . . . . ?
O1 C2 C3 C4 -179.59(13) . . . . ?
C12 C2 C3 C4 0.6(2) . . . . ?
C2 C3 C4 C5 1.0(2) . . . . ?
C3 C4 C5 C11 -1.6(2) . . . . ?
C3 C4 C5 C6 176.84(14) . . . . ?
C7 N1 C6 O2 1.4(2) . . . . ?
C7 N1 C6 C5 -178.74(13) . . . . ?
C4 C5 C6 O2 -151.66(15) . . . . ?
C11 C5 C6 O2 26.8(2) . . . . ?
C4 C5 C6 N1 28.5(2) . . . . ?
C11 C5 C6 N1 -153.07(14) . . . . ?
C6 N1 C7 C8 150.60(15) . . . . ?
C6 N1 C7 C13 -31.8(2) . . . . ?
C13 C7 C8 F1 179.15(14) . . . . ?
N1 C7 C8 F1 -3.1(2) . . . . ?
C13 C7 C8 C9 -0.8(2) . . . . ?
N1 C7 C8 C9 176.98(15) . . . . ?
F1 C8 C9 C10 -179.37(15) . . . . ?
C7 C8 C9 C10 0.5(3) . . . . ?
C8 C9 C10 C14 0.1(3) . . . . ?
C4 C5 C11 C12 0.5(2) . . . . ?
C6 C5 C11 C12 -178.01(14) . . . . ?
C5 C11 C12 C2 1.1(2) . . . . ?
O1 C2 C12 C11 178.51(14) . . . . ?
C3 C2 C12 C11 -1.6(2) . . . . ?
C8 C7 C13 C14 0.4(2) . . . . ?
N1 C7 C13 C14 -177.22(14) . . . . ?
C9 C10 C14 C13 -0.5(3) . . . . ?
C7 C13 C14 C10 0.2(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        66.52
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.187
_refine_diff_density_min         -0.203
_refine_diff_density_rms         0.045
_database_code_depnum_ccdc_archive 'CCDC 990222'
#######################################################################
#
#                 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_shelxl

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H15 F5 N2 O3'
_chemical_formula_weight         426.34

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'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           trigonal
_symmetry_space_group_name_H-M   R-3

loop_
_symmetry_equiv_pos_as_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                   24.8585(5)
_cell_length_b                   24.8585(5)
_cell_length_c                   16.8633(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                120.00
_cell_volume                     9024.5(3)
_cell_formula_units_Z            18
_cell_measurement_temperature    228(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.02
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.412
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             3924
_exptl_absorpt_coefficient_mu    1.108
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8006
_exptl_absorpt_correction_T_max  0.9782
_exptl_absorpt_process_details   'SADABS; (Sheldrick, 2003)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      228(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'BRUKER SMART APEXII CCD'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            22245
_diffrn_reflns_av_R_equivalents  0.0506
_diffrn_reflns_av_sigmaI/netI    0.0446
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         3.33
_diffrn_reflns_theta_max         66.77
_reflns_number_total             3555
_reflns_number_gt                2667
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2 (Bruker, 2010)'
_computing_cell_refinement       'APEX2 (Bruker, 2010); SAINT (Bruker, 2009)'
_computing_data_reduction        'SAINT (Bruker, 2009);XPREP(Sheldrick,2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008); OLEX2 (2009)'
_computing_molecular_graphics    ?
_computing_publication_material  'APEX2 (Bruker, 2010)'

_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)+(0.0351P)²+5.9780P] 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     SHELXL
_refine_ls_extinction_coef       0.000108(16)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3555
_refine_ls_number_parameters     275
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0585
_refine_ls_R_factor_gt           0.0428
_refine_ls_wR_factor_ref         0.1229
_refine_ls_wR_factor_gt          0.1095
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_restrained_S_all      1.043
_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 0.40120(10) 0.24899(9) 1.13612(10) 0.1449(7) Uani 1 1 d . . .
F2 F 0.51985(11) 0.31489(9) 1.18582(9) 0.1443(7) Uani 1 1 d . . .
O2 O 0.44418(7) 0.17166(7) 0.86463(9) 0.0811(4) Uani 1 1 d . . .
O3 O 0.49880(8) 0.34715(7) 0.56816(9) 0.0960(5) Uani 1 1 d . . .
C1 C 0.43146(17) 0.35389(15) 0.43029(19) 0.1295(11) Uani 1 1 d . . .
H1A H 0.4323 0.3732 0.3800 0.194 Uiso 1 1 calc R . .
H1B H 0.4620 0.3848 0.4657 0.194 Uiso 1 1 calc R . .
H1C H 0.3905 0.3366 0.4538 0.194 Uiso 1 1 calc R . .
C2 C 0.44629(12) 0.30306(11) 0.41694(13) 0.0899(7) Uani 1 1 d . . .
O4 O 0.43491(7) 0.26616(6) 0.49081(8) 0.0779(4) Uani 1 1 d . . .
C4 C 0.46327(9) 0.29329(9) 0.55698(12) 0.0699(5) Uani 1 1 d . . .
N5 N 0.44630(7) 0.24920(7) 0.61785(9) 0.0646(4) Uani 1 1 d . . .
C6 C 0.46489(9) 0.26816(9) 0.69505(12) 0.0666(5) Uani 1 1 d . . .
H6 H 0.4900 0.3096 0.7114 0.080 Uiso 1 1 calc R . .
C7 C 0.44158(8) 0.21809(9) 0.74368(12) 0.0644(5) Uani 1 1 d . . .
C27 C 0.45125(9) 0.21800(9) 0.82914(12) 0.0672(5) Uani 1 1 d . . .
N1 N 0.46862(9) 0.27193(8) 0.86763(10) 0.0775(5) Uani 1 1 d . . .
H1 H 0.4717 0.3033 0.8409 0.093 Uiso 1 1 calc R . .
C10 C 0.48197(10) 0.27941(9) 0.94923(12) 0.0689(5) Uani 1 1 d . . .
C11 C 0.54216(10) 0.31114(10) 0.97650(14) 0.0777(6) Uani 1 1 d . . .
C12 C 0.55511(13) 0.32351(11) 1.05576(18) 0.0903(7) Uani 1 1 d . . .
F3 F 0.61381(8) 0.35706(9) 1.08078(12) 0.1369(7) Uani 1 1 d . . .
C14 C 0.50728(16) 0.30242(12) 1.10847(14) 0.0923(7) Uani 1 1 d . . .
C15 C 0.44770(14) 0.26986(11) 1.08369(15) 0.0915(7) Uani 1 1 d . . .
C16 C 0.43519(10) 0.25875(10) 1.00440(13) 0.0776(6) Uani 1 1 d . . .
F5 F 0.37628(7) 0.22847(7) 0.98026(10) 0.1132(5) Uani 1 1 d . . .
F4 F 0.58919(7) 0.33254(8) 0.92499(10) 0.1143(5) Uani 1 1 d . . .
C19 C 0.40114(17) 0.25449(15) 0.35959(16) 0.1335(12) Uani 1 1 d . . .
H19A H 0.4108 0.2214 0.3544 0.200 Uiso 1 1 calc R . .
H19B H 0.4046 0.2734 0.3082 0.200 Uiso 1 1 calc R . .
H19C H 0.3591 0.2376 0.3794 0.200 Uiso 1 1 calc R . .
C20 C 0.51287(14) 0.32659(16) 0.39226(18) 0.1282(11) Uani 1 1 d . . .
H20A H 0.5216 0.2927 0.3937 0.192 Uiso 1 1 calc R . .
H20B H 0.5406 0.3590 0.4284 0.192 Uiso 1 1 calc R . .
H20C H 0.5192 0.3432 0.3389 0.192 Uiso 1 1 calc R . .
C21 C 0.40911(8) 0.18411(8) 0.61666(12) 0.0634(5) Uani 1 1 d . . .
C22 C 0.40599(8) 0.16366(8) 0.69502(12) 0.0643(5) Uani 1 1 d . . .
C23 C 0.37092(10) 0.10056(10) 0.71212(15) 0.0794(6) Uani 1 1 d . . .
H23 H 0.3677 0.0861 0.7644 0.095 Uiso 1 1 calc R . .
C24 C 0.34107(11) 0.05993(11) 0.65105(19) 0.0947(8) Uani 1 1 d . . .
H24 H 0.3171 0.0172 0.6617 0.114 Uiso 1 1 calc R . .
C25 C 0.34566(11) 0.08089(11) 0.57386(18) 0.0924(7) Uani 1 1 d . . .
H25 H 0.3250 0.0518 0.5333 0.111 Uiso 1 1 calc R . .
C26 C 0.37939(9) 0.14289(9) 0.55462(14) 0.0758(6) Uani 1 1 d . . .
H26 H 0.3822 0.1567 0.5021 0.091 Uiso 1 1 calc R . .


_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 C15 1.337(3) . ?
F2 C14 1.341(3) . ?
O2 C27 1.230(2) . ?
O3 C4 1.194(2) . ?
C1 C2 1.500(4) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C1 H1C 0.9700 . ?
C2 O4 1.488(3) . ?
C2 C20 1.512(4) . ?
C2 C19 1.516(4) . ?
O4 C4 1.312(2) . ?
C4 N5 1.404(3) . ?
N5 C6 1.383(2) . ?
N5 C21 1.406(2) . ?
C6 C7 1.355(3) . ?
C6 H6 0.9400 . ?
C7 C22 1.446(3) . ?
C7 C27 1.461(3) . ?
C27 N1 1.351(3) . ?
N1 C10 1.406(3) . ?
N1 H1 0.8700 . ?
C10 C16 1.373(3) . ?
C10 C11 1.376(3) . ?
C11 F4 1.335(3) . ?
C11 C12 1.373(3) . ?
C12 F3 1.336(3) . ?
C12 C14 1.362(4) . ?
C14 C15 1.351(4) . ?
C15 C16 1.369(3) . ?
C16 F5 1.332(3) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C19 H19C 0.9700 . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C20 H20C 0.9700 . ?
C21 C26 1.390(3) . ?
C21 C22 1.404(3) . ?
C22 C23 1.391(3) . ?
C23 C24 1.372(3) . ?
C23 H23 0.9400 . ?
C24 C25 1.385(4) . ?
C24 H24 0.9400 . ?
C25 C26 1.375(3) . ?
C25 H25 0.9400 . ?
C26 H26 0.9400 . ?

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 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O4 C2 C1 110.0(2) . . ?
O4 C2 C20 107.6(2) . . ?
C1 C2 C20 113.5(3) . . ?
O4 C2 C19 101.9(2) . . ?
C1 C2 C19 111.8(3) . . ?
C20 C2 C19 111.3(2) . . ?
C4 O4 C2 120.49(16) . . ?
O3 C4 O4 128.09(19) . . ?
O3 C4 N5 121.67(18) . . ?
O4 C4 N5 110.24(17) . . ?
C6 N5 C4 120.23(16) . . ?
C6 N5 C21 108.72(16) . . ?
C4 N5 C21 131.00(17) . . ?
C7 C6 N5 109.88(17) . . ?
C7 C6 H6 125.1 . . ?
N5 C6 H6 125.1 . . ?
C6 C7 C22 107.26(18) . . ?
C6 C7 C27 127.09(18) . . ?
C22 C7 C27 125.63(17) . . ?
O2 C27 N1 121.36(19) . . ?
O2 C27 C7 122.31(18) . . ?
N1 C27 C7 116.33(17) . . ?
C27 N1 C10 122.59(16) . . ?
C27 N1 H1 118.7 . . ?
C10 N1 H1 118.7 . . ?
C16 C10 C11 117.6(2) . . ?
C16 C10 N1 120.9(2) . . ?
C11 C10 N1 121.34(19) . . ?
F4 C11 C12 118.9(2) . . ?
F4 C11 C10 119.7(2) . . ?
C12 C11 C10 121.3(2) . . ?
F3 C12 C14 120.3(3) . . ?
F3 C12 C11 120.5(3) . . ?
C14 C12 C11 119.2(2) . . ?
F2 C14 C15 119.9(3) . . ?
F2 C14 C12 119.2(3) . . ?
C15 C14 C12 120.9(2) . . ?
F1 C15 C14 120.3(3) . . ?
F1 C15 C16 120.2(3) . . ?
C14 C15 C16 119.6(2) . . ?
F5 C16 C15 119.1(2) . . ?
F5 C16 C10 119.4(2) . . ?
C15 C16 C10 121.5(2) . . ?
C2 C19 H19A 109.5 . . ?
C2 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C2 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C2 C20 H20A 109.5 . . ?
C2 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C2 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C26 C21 C22 121.90(18) . . ?
C26 C21 N5 131.30(19) . . ?
C22 C21 N5 106.79(16) . . ?
C23 C22 C21 119.56(19) . . ?
C23 C22 C7 133.1(2) . . ?
C21 C22 C7 107.34(16) . . ?
C24 C23 C22 118.5(2) . . ?
C24 C23 H23 120.7 . . ?
C22 C23 H23 120.7 . . ?
C23 C24 C25 121.1(2) . . ?
C23 C24 H24 119.5 . . ?
C25 C24 H24 119.5 . . ?
C26 C25 C24 122.2(2) . . ?
C26 C25 H25 118.9 . . ?
C24 C25 H25 118.9 . . ?
C25 C26 C21 116.7(2) . . ?
C25 C26 H26 121.6 . . ?
C21 C26 H26 121.6 . . ?

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
C1 C2 O4 C4 -57.1(3) . . . . ?
C20 C2 O4 C4 67.0(3) . . . . ?
C19 C2 O4 C4 -175.8(2) . . . . ?
C2 O4 C4 O3 1.2(3) . . . . ?
C2 O4 C4 N5 -178.79(18) . . . . ?
O3 C4 N5 C6 7.6(3) . . . . ?
O4 C4 N5 C6 -172.46(16) . . . . ?
O3 C4 N5 C21 -175.3(2) . . . . ?
O4 C4 N5 C21 4.6(3) . . . . ?
C4 N5 C6 C7 178.02(16) . . . . ?
C21 N5 C6 C7 0.3(2) . . . . ?
N5 C6 C7 C22 0.1(2) . . . . ?
N5 C6 C7 C27 178.82(17) . . . . ?
C6 C7 C27 O2 -158.5(2) . . . . ?
C22 C7 C27 O2 20.0(3) . . . . ?
C6 C7 C27 N1 21.3(3) . . . . ?
C22 C7 C27 N1 -160.17(18) . . . . ?
O2 C27 N1 C10 2.5(3) . . . . ?
C7 C27 N1 C10 -177.39(18) . . . . ?
C27 N1 C10 C16 -81.0(3) . . . . ?
C27 N1 C10 C11 103.3(2) . . . . ?
C16 C10 C11 F4 -179.49(18) . . . . ?
N1 C10 C11 F4 -3.6(3) . . . . ?
C16 C10 C11 C12 -2.1(3) . . . . ?
N1 C10 C11 C12 173.79(18) . . . . ?
F4 C11 C12 F3 0.8(3) . . . . ?
C10 C11 C12 F3 -176.65(19) . . . . ?
F4 C11 C12 C14 179.2(2) . . . . ?
C10 C11 C12 C14 1.8(3) . . . . ?
F3 C12 C14 F2 -1.0(3) . . . . ?
C11 C12 C14 F2 -179.47(19) . . . . ?
F3 C12 C14 C15 178.2(2) . . . . ?
C11 C12 C14 C15 -0.2(3) . . . . ?
F2 C14 C15 F1 -1.3(4) . . . . ?
C12 C14 C15 F1 179.5(2) . . . . ?
F2 C14 C15 C16 178.2(2) . . . . ?
C12 C14 C15 C16 -1.0(4) . . . . ?
F1 C15 C16 F5 1.8(3) . . . . ?
C14 C15 C16 F5 -177.7(2) . . . . ?
F1 C15 C16 C10 -179.8(2) . . . . ?
C14 C15 C16 C10 0.7(4) . . . . ?
C11 C10 C16 F5 179.22(18) . . . . ?
N1 C10 C16 F5 3.4(3) . . . . ?
C11 C10 C16 C15 0.8(3) . . . . ?
N1 C10 C16 C15 -175.1(2) . . . . ?
C6 N5 C21 C26 -179.99(19) . . . . ?
C4 N5 C21 C26 2.7(3) . . . . ?
C6 N5 C21 C22 -0.63(19) . . . . ?
C4 N5 C21 C22 -178.00(18) . . . . ?
C26 C21 C22 C23 -1.7(3) . . . . ?
N5 C21 C22 C23 178.83(16) . . . . ?
C26 C21 C22 C7 -179.88(16) . . . . ?
N5 C21 C22 C7 0.69(19) . . . . ?
C6 C7 C22 C23 -178.3(2) . . . . ?
C27 C7 C22 C23 3.0(3) . . . . ?
C6 C7 C22 C21 -0.5(2) . . . . ?
C27 C7 C22 C21 -179.24(17) . . . . ?
C21 C22 C23 C24 1.0(3) . . . . ?
C7 C22 C23 C24 178.6(2) . . . . ?
C22 C23 C24 C25 0.2(3) . . . . ?
C23 C24 C25 C26 -0.8(4) . . . . ?
C24 C25 C26 C21 0.1(3) . . . . ?
C22 C21 C26 C25 1.1(3) . . . . ?
N5 C21 C26 C25 -179.58(19) . . . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        66.60
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.153
_refine_diff_density_min         -0.157
_refine_diff_density_rms         0.028
_database_code_depnum_ccdc_archive 'CCDC 990223'
