# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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_a

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C10 H6 F N O2'
_chemical_formula_sum            'C10 H6 F N O2'
_chemical_formula_weight         191.16

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           orthorhombic
_symmetry_space_group_name_H-M   Pbca

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

_cell_length_a                   10.892(2)
_cell_length_b                   7.9279(18)
_cell_length_c                   19.835(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1712.9(7)
_cell_formula_units_Z            8
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    3922
_cell_measurement_theta_min      1.87
_cell_measurement_theta_max      27.48

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.483
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             784
_exptl_absorpt_coefficient_mu    0.119
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9652
_exptl_absorpt_correction_T_max  0.9824
_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            4891
_diffrn_reflns_av_R_equivalents  0.0398
_diffrn_reflns_av_sigmaI/netI    0.0321
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.05
_diffrn_reflns_theta_max         25.00
_reflns_number_total             1498
_reflns_number_gt                1377
_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  'SHELXL-97 (Sheldrick, 2008)'
_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)+(0.0257P)²+0.7777P] 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         1498
_refine_ls_number_parameters     137
_refine_ls_number_restraints     13
_refine_ls_R_factor_all          0.0680
_refine_ls_R_factor_gt           0.0601
_refine_ls_wR_factor_ref         0.1175
_refine_ls_wR_factor_gt          0.1140
_refine_ls_goodness_of_fit_ref   1.287
_refine_ls_restrained_S_all      1.287
_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 0.44746(14) -0.0244(2) 0.66057(9) 0.0526(6) Uani 0.805(4) 1 d PDU A 1
F1' F 0.8138(6) 0.2589(10) 0.6563(4) 0.059(3) Uani 0.195(4) 1 d PDU A 2
O1 O 0.80231(17) 0.0347(3) 0.56387(10) 0.0732(7) Uani 1 1 d . . .
O2 O 0.43281(14) 0.2970(2) 0.58483(8) 0.0569(5) Uani 1 1 d . . .
N1 N 0.61850(16) 0.1577(2) 0.59349(9) 0.0420(5) Uani 1 1 d . . .
C1 C 0.62468(19) 0.1391(3) 0.66477(11) 0.0385(5) Uani 1 1 d . A .
C2 C 0.5353(2) 0.0501(3) 0.69857(12) 0.0412(6) Uani 1 1 d D . .
H1 H 0.4689 0.0013 0.6735 0.049 Uiso 0.195(4) 1 d PR A .
C3 C 0.5364(2) 0.0303(3) 0.76728(12) 0.0483(7) Uani 1 1 d . A .
H3 H 0.4725 -0.0294 0.7895 0.058 Uiso 1 1 calc R . .
C4 C 0.6323(2) 0.0990(3) 0.80329(13) 0.0501(7) Uani 1 1 d . . .
H4 H 0.6352 0.0856 0.8509 0.060 Uiso 1 1 calc R A .
C5 C 0.7241(2) 0.1870(3) 0.77072(13) 0.0527(7) Uani 1 1 d . A .
H5 H 0.7903 0.2332 0.7958 0.063 Uiso 1 1 calc R . .
C6 C 0.7197(2) 0.2081(3) 0.70175(13) 0.0472(6) Uani 1 1 d D . .
H1' H 0.7831 0.2709 0.6793 0.057 Uiso 0.805(4) 1 d PR A .
C7 C 0.7079(2) 0.1037(3) 0.54802(13) 0.0511(7) Uani 1 1 d . . .
C8 C 0.6619(2) 0.1499(3) 0.48013(13) 0.0526(7) Uani 1 1 d . . .
H8 H 0.7027 0.1278 0.4387 0.063 Uiso 1 1 calc R . .
C9 C 0.5554(2) 0.2265(3) 0.48641(12) 0.0514(7) Uani 1 1 d . . .
H9 H 0.5073 0.2689 0.4503 0.062 Uiso 1 1 calc R . .
C10 C 0.5224(2) 0.2362(3) 0.55888(12) 0.0444(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
F1 C2 1.354(3) . ?
F1 H1 0.4023 . ?
F1' C6 1.424(7) . ?
F1' H1' 0.5755 . ?
O1 C7 1.206(3) . ?
O2 C10 1.204(3) . ?
N1 C7 1.395(3) . ?
N1 C10 1.398(3) . ?
N1 C1 1.423(3) . ?
C1 C2 1.376(3) . ?
C1 C6 1.381(3) . ?
C2 C3 1.372(3) . ?
C2 H1 0.9596 . ?
C3 C4 1.377(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.380(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.379(3) . ?
C5 H5 0.9500 . ?
C6 H1' 0.9601 . ?
C7 C8 1.483(4) . ?
C8 C9 1.315(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.484(3) . ?
C9 H9 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 F1 H1 9.5 . . ?
C6 F1' H1' 28.7 . . ?
C7 N1 C10 110.0(2) . . ?
C7 N1 C1 125.3(2) . . ?
C10 N1 C1 124.70(18) . . ?
C2 C1 C6 118.3(2) . . ?
C2 C1 N1 120.2(2) . . ?
C6 C1 N1 121.5(2) . . ?
F1 C2 C3 120.6(2) . . ?
F1 C2 C1 116.9(2) . . ?
C3 C2 C1 122.5(2) . . ?
F1 C2 H1 4.0 . . ?
C3 C2 H1 118.4 . . ?
C1 C2 H1 119.2 . . ?
C2 C3 C4 118.4(2) . . ?
C2 C3 H3 120.8 . . ?
C4 C3 H3 120.8 . . ?
C3 C4 C5 120.4(2) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 H4 119.8 . . ?
C6 C5 C4 120.0(2) . . ?
C6 C5 H5 120.0 . . ?
C4 C5 H5 120.0 . . ?
C5 C6 C1 120.3(2) . . ?
C5 C6 F1' 129.6(4) . . ?
C1 C6 F1' 108.4(4) . . ?
C5 C6 H1' 119.8 . . ?
C1 C6 H1' 119.9 . . ?
F1' C6 H1' 16.7 . . ?
O1 C7 N1 124.5(3) . . ?
O1 C7 C8 129.6(2) . . ?
N1 C7 C8 106.0(2) . . ?
C9 C8 C7 109.0(2) . . ?
C9 C8 H8 125.5 . . ?
C7 C8 H8 125.5 . . ?
C8 C9 C10 109.2(2) . . ?
C8 C9 H9 125.4 . . ?
C10 C9 H9 125.4 . . ?
O2 C10 N1 125.1(2) . . ?
O2 C10 C9 129.2(2) . . ?
N1 C10 C9 105.7(2) . . ?

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
C7 N1 C1 C2 -120.7(2) . . . . ?
C10 N1 C1 C2 60.6(3) . . . . ?
C7 N1 C1 C6 58.9(3) . . . . ?
C10 N1 C1 C6 -119.8(2) . . . . ?
C6 C1 C2 F1 -176.2(2) . . . . ?
N1 C1 C2 F1 3.4(3) . . . . ?
C6 C1 C2 C3 1.1(3) . . . . ?
N1 C1 C2 C3 -179.2(2) . . . . ?
F1 C2 C3 C4 175.7(2) . . . . ?
C1 C2 C3 C4 -1.6(4) . . . . ?
C2 C3 C4 C5 0.7(4) . . . . ?
C3 C4 C5 C6 0.6(4) . . . . ?
C4 C5 C6 C1 -1.0(4) . . . . ?
C4 C5 C6 F1' -164.4(5) . . . . ?
C2 C1 C6 C5 0.2(3) . . . . ?
N1 C1 C6 C5 -179.4(2) . . . . ?
C2 C1 C6 F1' 166.8(4) . . . . ?
N1 C1 C6 F1' -12.9(4) . . . . ?
C10 N1 C7 O1 178.6(3) . . . . ?
C1 N1 C7 O1 -0.3(4) . . . . ?
C10 N1 C7 C8 -1.1(3) . . . . ?
C1 N1 C7 C8 -179.9(2) . . . . ?
O1 C7 C8 C9 -178.8(3) . . . . ?
N1 C7 C8 C9 0.8(3) . . . . ?
C7 C8 C9 C10 -0.3(3) . . . . ?
C7 N1 C10 O2 -179.2(2) . . . . ?
C1 N1 C10 O2 -0.4(4) . . . . ?
C7 N1 C10 C9 0.9(3) . . . . ?
C1 N1 C10 C9 179.8(2) . . . . ?
C8 C9 C10 O2 179.8(3) . . . . ?
C8 C9 C10 N1 -0.4(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.155
_refine_diff_density_min         -0.168
_refine_diff_density_rms         0.036
_database_code_depnum_ccdc_archive 'CCDC 940166'
#######################################################################
#
#                 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_a

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C26 H14 F5 N O4'
_chemical_formula_sum            'C26 H14 F5 N O4'
_chemical_formula_weight         499.38

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           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                   12.761(3)
_cell_length_b                   20.483(4)
_cell_length_c                   8.2482(15)
_cell_angle_alpha                90.00
_cell_angle_beta                 98.692(3)
_cell_angle_gamma                90.00
_cell_volume                     2131.2(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    5932
_cell_measurement_theta_min      1.90
_cell_measurement_theta_max      27.47

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.52
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.24
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.556
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1016
_exptl_absorpt_coefficient_mu    0.134
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9335
_exptl_absorpt_correction_T_max  0.9685
_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            14409
_diffrn_reflns_av_R_equivalents  0.0387
_diffrn_reflns_av_sigmaI/netI    0.0360
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         1.99
_diffrn_reflns_theta_max         27.49
_reflns_number_total             4881
_reflns_number_gt                4539
_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  'SHELXL-97 (Sheldrick, 2008)'
_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)+(0.0498P)²+1.0011P] 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         4881
_refine_ls_number_parameters     326
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0600
_refine_ls_R_factor_gt           0.0548
_refine_ls_wR_factor_ref         0.1316
_refine_ls_wR_factor_gt          0.1284
_refine_ls_goodness_of_fit_ref   1.158
_refine_ls_restrained_S_all      1.158
_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 -0.07043(10) 0.38998(6) 0.33001(16) 0.0398(3) Uani 1 1 d . . .
F2 F -0.25850(11) 0.34195(8) 0.18285(19) 0.0559(4) Uani 1 1 d . . .
F3 F -0.29995(10) 0.21276(8) 0.19943(19) 0.0580(4) Uani 1 1 d . . .
F4 F -0.15977(11) 0.13269(6) 0.3808(2) 0.0538(4) Uani 1 1 d . . .
F5 F 0.02684(10) 0.18083(5) 0.53554(16) 0.0387(3) Uani 1 1 d . . .
O1 O 0.02170(11) 0.38131(6) 0.69017(16) 0.0291(3) Uani 1 1 d . . .
O2 O 0.18550(10) 0.25024(6) 0.35865(16) 0.0303(3) Uani 1 1 d . . .
O3 O 0.43950(13) 0.33051(7) 0.25150(18) 0.0397(4) Uani 1 1 d . . .
O4 O 0.43264(11) 0.26504(7) 0.46707(16) 0.0323(3) Uani 1 1 d . . .
N1 N 0.08251(12) 0.31050(7) 0.50889(18) 0.0232(3) Uani 1 1 d . . .
C1 C 0.21094(14) 0.37440(8) 0.6722(2) 0.0220(3) Uani 1 1 d . . .
H1 H 0.2359 0.3679 0.7920 0.026 Uiso 1 1 calc R . .
C2 C 0.23452(14) 0.44575(8) 0.6218(2) 0.0230(4) Uani 1 1 d . . .
H2 H 0.1960 0.4788 0.6799 0.028 Uiso 1 1 calc R . .
C3 C 0.35326(15) 0.45316(9) 0.6616(2) 0.0243(4) Uani 1 1 d . . .
C4 C 0.40971(14) 0.40926(8) 0.5778(2) 0.0235(4) Uani 1 1 d . . .
C5 C 0.33784(14) 0.36360(8) 0.4617(2) 0.0222(3) Uani 1 1 d . . .
C6 C 0.26739(14) 0.32598(8) 0.5713(2) 0.0209(3) Uani 1 1 d . . .
H6 H 0.3118 0.2949 0.6458 0.025 Uiso 1 1 calc R . .
C7 C 0.17886(14) 0.28956(8) 0.4649(2) 0.0232(4) Uani 1 1 d . . .
C8 C 0.09450(14) 0.35825(8) 0.6323(2) 0.0229(4) Uani 1 1 d . . .
C9 C 0.20508(14) 0.45001(8) 0.4372(2) 0.0227(3) Uani 1 1 d . . .
C10 C 0.12936(15) 0.49176(9) 0.3565(2) 0.0265(4) Uani 1 1 d . . .
H10 H 0.0924 0.5211 0.4169 0.032 Uiso 1 1 calc R . .
C11 C 0.10794(16) 0.49034(9) 0.1861(2) 0.0303(4) Uani 1 1 d . . .
H11 H 0.0570 0.5193 0.1293 0.036 Uiso 1 1 calc R . .
C12 C 0.16107(16) 0.44656(9) 0.0991(2) 0.0307(4) Uani 1 1 d . . .
H12 H 0.1451 0.4453 -0.0172 0.037 Uiso 1 1 calc R . .
C13 C 0.23738(15) 0.40453(9) 0.1795(2) 0.0264(4) Uani 1 1 d . . .
H13 H 0.2733 0.3747 0.1189 0.032 Uiso 1 1 calc R . .
C14 C 0.26050(14) 0.40679(8) 0.3494(2) 0.0219(3) Uani 1 1 d . . .
C15 C -0.01729(14) 0.28628(9) 0.4343(2) 0.0251(4) Uani 1 1 d . . .
C16 C -0.09169(15) 0.32669(9) 0.3458(2) 0.0295(4) Uani 1 1 d . . .
C17 C -0.18764(16) 0.30243(11) 0.2692(3) 0.0375(5) Uani 1 1 d . . .
C18 C -0.20898(16) 0.23672(12) 0.2787(3) 0.0388(5) Uani 1 1 d . . .
C19 C -0.13694(17) 0.19588(10) 0.3684(3) 0.0363(5) Uani 1 1 d . . .
C20 C -0.04171(15) 0.22050(9) 0.4462(2) 0.0287(4) Uani 1 1 d . . .
C21 C 0.40689(16) 0.49845(9) 0.7685(2) 0.0300(4) Uani 1 1 d . . .
H21 H 0.3686 0.5281 0.8260 0.036 Uiso 1 1 calc R . .
C22 C 0.51695(17) 0.50009(10) 0.7910(2) 0.0344(4) Uani 1 1 d . . .
H22 H 0.5541 0.5312 0.8637 0.041 Uiso 1 1 calc R . .
C23 C 0.57298(16) 0.45649(10) 0.7077(2) 0.0331(4) Uani 1 1 d . . .
H23 H 0.6483 0.4578 0.7240 0.040 Uiso 1 1 calc R . .
C24 C 0.51951(15) 0.41089(9) 0.6005(2) 0.0282(4) Uani 1 1 d . . .
H24 H 0.5579 0.3812 0.5434 0.034 Uiso 1 1 calc R . .
C25 C 0.40679(14) 0.31835(9) 0.3770(2) 0.0254(4) Uani 1 1 d . . .
C26 C 0.50666(18) 0.22045(11) 0.4094(3) 0.0412(5) Uani 1 1 d . . .
H26A H 0.4819 0.2094 0.2944 0.062 Uiso 1 1 calc R . .
H26B H 0.5117 0.1806 0.4759 0.062 Uiso 1 1 calc R . .
H26C H 0.5766 0.2411 0.4189 0.062 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 C16 1.335(2) . ?
F2 C17 1.336(2) . ?
F3 C18 1.337(2) . ?
F4 C19 1.334(2) . ?
F5 C20 1.332(2) . ?
O1 C8 1.203(2) . ?
O2 C7 1.203(2) . ?
O3 C25 1.199(2) . ?
O4 C25 1.334(2) . ?
O4 C26 1.445(2) . ?
N1 C7 1.401(2) . ?
N1 C8 1.403(2) . ?
N1 C15 1.418(2) . ?
C1 C8 1.509(2) . ?
C1 C6 1.542(2) . ?
C1 C2 1.561(2) . ?
C1 H1 1.0000 . ?
C2 C3 1.509(3) . ?
C2 C9 1.515(2) . ?
C2 H2 1.0000 . ?
C3 C21 1.387(3) . ?
C3 C4 1.399(3) . ?
C4 C24 1.386(3) . ?
C4 C5 1.539(2) . ?
C5 C25 1.519(2) . ?
C5 C14 1.529(2) . ?
C5 C6 1.570(2) . ?
C6 C7 1.517(2) . ?
C6 H6 1.0000 . ?
C9 C10 1.383(2) . ?
C9 C14 1.401(2) . ?
C10 C11 1.391(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.388(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.391(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.389(2) . ?
C13 H13 0.9500 . ?
C15 C16 1.382(3) . ?
C15 C20 1.390(3) . ?
C16 C17 1.383(3) . ?
C17 C18 1.378(3) . ?
C18 C19 1.374(3) . ?
C19 C20 1.381(3) . ?
C21 C22 1.389(3) . ?
C21 H21 0.9500 . ?
C22 C23 1.389(3) . ?
C22 H22 0.9500 . ?
C23 C24 1.392(3) . ?
C23 H23 0.9500 . ?
C24 H24 0.9500 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?

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
C25 O4 C26 116.94(15) . . ?
C7 N1 C8 113.42(15) . . ?
C7 N1 C15 123.13(14) . . ?
C8 N1 C15 123.45(15) . . ?
C8 C1 C6 105.43(14) . . ?
C8 C1 C2 111.71(14) . . ?
C6 C1 C2 109.50(13) . . ?
C8 C1 H1 110.0 . . ?
C6 C1 H1 110.0 . . ?
C2 C1 H1 110.0 . . ?
C3 C2 C9 107.53(14) . . ?
C3 C2 C1 105.30(14) . . ?
C9 C2 C1 107.06(13) . . ?
C3 C2 H2 112.2 . . ?
C9 C2 H2 112.2 . . ?
C1 C2 H2 112.2 . . ?
C21 C3 C4 120.18(18) . . ?
C21 C3 C2 126.04(17) . . ?
C4 C3 C2 113.78(15) . . ?
C24 C4 C3 120.24(17) . . ?
C24 C4 C5 126.46(16) . . ?
C3 C4 C5 113.29(15) . . ?
C25 C5 C14 116.11(14) . . ?
C25 C5 C4 108.96(14) . . ?
C14 C5 C4 107.14(14) . . ?
C25 C5 C6 112.78(14) . . ?
C14 C5 C6 105.04(14) . . ?
C4 C5 C6 106.23(13) . . ?
C7 C6 C1 105.11(14) . . ?
C7 C6 C5 110.46(13) . . ?
C1 C6 C5 110.49(14) . . ?
C7 C6 H6 110.2 . . ?
C1 C6 H6 110.2 . . ?
C5 C6 H6 110.2 . . ?
O2 C7 N1 123.71(17) . . ?
O2 C7 C6 128.47(16) . . ?
N1 C7 C6 107.81(14) . . ?
O1 C8 N1 123.73(17) . . ?
O1 C8 C1 128.38(16) . . ?
N1 C8 C1 107.88(14) . . ?
C10 C9 C14 120.84(16) . . ?
C10 C9 C2 124.63(16) . . ?
C14 C9 C2 114.52(15) . . ?
C9 C10 C11 119.30(17) . . ?
C9 C10 H10 120.3 . . ?
C11 C10 H10 120.3 . . ?
C12 C11 C10 119.96(17) . . ?
C12 C11 H11 120.0 . . ?
C10 C11 H11 120.0 . . ?
C11 C12 C13 120.98(17) . . ?
C11 C12 H12 119.5 . . ?
C13 C12 H12 119.5 . . ?
C14 C13 C12 119.17(17) . . ?
C14 C13 H13 120.4 . . ?
C12 C13 H13 120.4 . . ?
C13 C14 C9 119.71(16) . . ?
C13 C14 C5 127.68(16) . . ?
C9 C14 C5 112.50(14) . . ?
C16 C15 C20 118.34(17) . . ?
C16 C15 N1 121.33(16) . . ?
C20 C15 N1 120.32(17) . . ?
F1 C16 C15 119.98(17) . . ?
F1 C16 C17 118.91(18) . . ?
C15 C16 C17 121.08(18) . . ?
F2 C17 C18 119.91(19) . . ?
F2 C17 C16 120.5(2) . . ?
C18 C17 C16 119.6(2) . . ?
F3 C18 C19 120.1(2) . . ?
F3 C18 C17 119.7(2) . . ?
C19 C18 C17 120.25(19) . . ?
F4 C19 C18 119.74(19) . . ?
F4 C19 C20 120.4(2) . . ?
C18 C19 C20 119.88(19) . . ?
F5 C20 C19 119.50(17) . . ?
F5 C20 C15 119.69(17) . . ?
C19 C20 C15 120.80(19) . . ?
C3 C21 C22 119.52(19) . . ?
C3 C21 H21 120.2 . . ?
C22 C21 H21 120.2 . . ?
C21 C22 C23 120.27(18) . . ?
C21 C22 H22 119.9 . . ?
C23 C22 H22 119.9 . . ?
C22 C23 C24 120.41(19) . . ?
C22 C23 H23 119.8 . . ?
C24 C23 H23 119.8 . . ?
C4 C24 C23 119.37(18) . . ?
C4 C24 H24 120.3 . . ?
C23 C24 H24 120.3 . . ?
O3 C25 O4 124.18(17) . . ?
O3 C25 C5 124.87(17) . . ?
O4 C25 C5 110.79(14) . . ?
O4 C26 H26A 109.5 . . ?
O4 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
O4 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?

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
C8 C1 C2 C3 -177.35(14) . . . . ?
C6 C1 C2 C3 -60.94(17) . . . . ?
C8 C1 C2 C9 -63.11(18) . . . . ?
C6 C1 C2 C9 53.30(18) . . . . ?
C9 C2 C3 C21 125.42(18) . . . . ?
C1 C2 C3 C21 -120.67(18) . . . . ?
C9 C2 C3 C4 -53.96(19) . . . . ?
C1 C2 C3 C4 59.95(18) . . . . ?
C21 C3 C4 C24 -0.2(3) . . . . ?
C2 C3 C4 C24 179.17(15) . . . . ?
C21 C3 C4 C5 -178.73(15) . . . . ?
C2 C3 C4 C5 0.7(2) . . . . ?
C24 C4 C5 C25 1.5(2) . . . . ?
C3 C4 C5 C25 179.84(14) . . . . ?
C24 C4 C5 C14 -124.89(18) . . . . ?
C3 C4 C5 C14 53.47(18) . . . . ?
C24 C4 C5 C6 123.23(18) . . . . ?
C3 C4 C5 C6 -58.40(18) . . . . ?
C8 C1 C6 C7 5.93(17) . . . . ?
C2 C1 C6 C7 -114.39(15) . . . . ?
C8 C1 C6 C5 125.10(14) . . . . ?
C2 C1 C6 C5 4.78(19) . . . . ?
C25 C5 C6 C7 -71.87(18) . . . . ?
C14 C5 C6 C7 55.51(17) . . . . ?
C4 C5 C6 C7 168.84(14) . . . . ?
C25 C5 C6 C1 172.26(14) . . . . ?
C14 C5 C6 C1 -60.37(17) . . . . ?
C4 C5 C6 C1 52.96(17) . . . . ?
C8 N1 C7 O2 -177.91(17) . . . . ?
C15 N1 C7 O2 1.4(3) . . . . ?
C8 N1 C7 C6 0.98(19) . . . . ?
C15 N1 C7 C6 -179.76(15) . . . . ?
C1 C6 C7 O2 174.44(18) . . . . ?
C5 C6 C7 O2 55.3(2) . . . . ?
C1 C6 C7 N1 -4.38(17) . . . . ?
C5 C6 C7 N1 -123.57(15) . . . . ?
C7 N1 C8 O1 -177.97(16) . . . . ?
C15 N1 C8 O1 2.8(3) . . . . ?
C7 N1 C8 C1 2.97(19) . . . . ?
C15 N1 C8 C1 -176.29(15) . . . . ?
C6 C1 C8 O1 175.47(17) . . . . ?
C2 C1 C8 O1 -65.7(2) . . . . ?
C6 C1 C8 N1 -5.53(18) . . . . ?
C2 C1 C8 N1 113.33(15) . . . . ?
C3 C2 C9 C10 -127.43(18) . . . . ?
C1 C2 C9 C10 119.84(18) . . . . ?
C3 C2 C9 C14 53.36(19) . . . . ?
C1 C2 C9 C14 -59.37(19) . . . . ?
C14 C9 C10 C11 0.3(3) . . . . ?
C2 C9 C10 C11 -178.84(17) . . . . ?
C9 C10 C11 C12 1.1(3) . . . . ?
C10 C11 C12 C13 -1.2(3) . . . . ?
C11 C12 C13 C14 -0.1(3) . . . . ?
C12 C13 C14 C9 1.5(3) . . . . ?
C12 C13 C14 C5 177.49(17) . . . . ?
C10 C9 C14 C13 -1.7(3) . . . . ?
C2 C9 C14 C13 177.59(16) . . . . ?
C10 C9 C14 C5 -178.19(15) . . . . ?
C2 C9 C14 C5 1.1(2) . . . . ?
C25 C5 C14 C13 7.8(3) . . . . ?
C4 C5 C14 C13 129.77(18) . . . . ?
C6 C5 C14 C13 -117.54(19) . . . . ?
C25 C5 C14 C9 -176.03(15) . . . . ?
C4 C5 C14 C9 -54.03(18) . . . . ?
C6 C5 C14 C9 58.65(18) . . . . ?
C7 N1 C15 C16 -116.80(19) . . . . ?
C8 N1 C15 C16 62.4(2) . . . . ?
C7 N1 C15 C20 62.0(2) . . . . ?
C8 N1 C15 C20 -118.82(19) . . . . ?
C20 C15 C16 F1 -179.17(17) . . . . ?
N1 C15 C16 F1 -0.4(3) . . . . ?
C20 C15 C16 C17 -0.8(3) . . . . ?
N1 C15 C16 C17 178.06(17) . . . . ?
F1 C16 C17 F2 -1.0(3) . . . . ?
C15 C16 C17 F2 -179.42(18) . . . . ?
F1 C16 C17 C18 177.35(18) . . . . ?
C15 C16 C17 C18 -1.1(3) . . . . ?
F2 C17 C18 F3 1.0(3) . . . . ?
C16 C17 C18 F3 -177.39(18) . . . . ?
F2 C17 C18 C19 -179.42(19) . . . . ?
C16 C17 C18 C19 2.2(3) . . . . ?
F3 C18 C19 F4 -2.4(3) . . . . ?
C17 C18 C19 F4 178.02(19) . . . . ?
F3 C18 C19 C20 178.10(18) . . . . ?
C17 C18 C19 C20 -1.5(3) . . . . ?
F4 C19 C20 F5 -0.8(3) . . . . ?
C18 C19 C20 F5 178.72(18) . . . . ?
F4 C19 C20 C15 -179.89(17) . . . . ?
C18 C19 C20 C15 -0.4(3) . . . . ?
C16 C15 C20 F5 -177.60(16) . . . . ?
N1 C15 C20 F5 3.6(3) . . . . ?
C16 C15 C20 C19 1.5(3) . . . . ?
N1 C15 C20 C19 -177.35(17) . . . . ?
C4 C3 C21 C22 0.3(3) . . . . ?
C2 C3 C21 C22 -179.01(17) . . . . ?
C3 C21 C22 C23 -0.3(3) . . . . ?
C21 C22 C23 C24 0.2(3) . . . . ?
C3 C4 C24 C23 0.1(3) . . . . ?
C5 C4 C24 C23 178.41(16) . . . . ?
C22 C23 C24 C4 -0.1(3) . . . . ?
C26 O4 C25 O3 1.4(3) . . . . ?
C26 O4 C25 C5 -174.13(16) . . . . ?
C14 C5 C25 O3 33.1(3) . . . . ?
C4 C5 C25 O3 -88.0(2) . . . . ?
C6 C5 C25 O3 154.33(19) . . . . ?
C14 C5 C25 O4 -151.46(15) . . . . ?
C4 C5 C25 O4 87.52(17) . . . . ?
C6 C5 C25 O4 -30.2(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        27.49
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.363
_refine_diff_density_min         -0.227
_refine_diff_density_rms         0.059
_database_code_depnum_ccdc_archive 'CCDC 940168'
#######################################################################
#
#                 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_sa2289

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C26 H17 F2 N O4'
_chemical_formula_sum            'C26 H17 F2 N O4'
_chemical_formula_weight         445.41

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                   9.309(2)
_cell_length_b                   9.593(2)
_cell_length_c                   12.074(3)
_cell_angle_alpha                76.314(10)
_cell_angle_beta                 76.794(10)
_cell_angle_gamma                79.813(10)
_cell_volume                     1011.3(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    3620
_cell_measurement_theta_min      1.77
_cell_measurement_theta_max      27.47

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.463
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             460
_exptl_absorpt_coefficient_mu    0.111
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6876
_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            13365
_diffrn_reflns_av_R_equivalents  0.0424
_diffrn_reflns_av_sigmaI/netI    0.0381
_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       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.77
_diffrn_reflns_theta_max         27.48
_reflns_number_total             4630
_reflns_number_gt                4211
_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  'SHELXL-97 (Sheldrick, 2008)'
_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)+(0.0404P)²+0.4191P] 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         4630
_refine_ls_number_parameters     299
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0597
_refine_ls_R_factor_gt           0.0528
_refine_ls_wR_factor_ref         0.1198
_refine_ls_wR_factor_gt          0.1158
_refine_ls_goodness_of_fit_ref   1.133
_refine_ls_restrained_S_all      1.133
_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 0.13250(12) 0.26974(12) 0.35483(9) 0.0389(3) Uani 1 1 d . . .
F2 F 0.50545(12) 0.31523(13) 0.54180(9) 0.0405(3) Uani 1 1 d . . .
O1 O 0.23094(15) 0.00322(13) 0.52292(11) 0.0353(3) Uani 1 1 d . . .
O2 O 0.18997(14) 0.42910(13) 0.64073(11) 0.0337(3) Uani 1 1 d . . .
O3 O -0.25210(18) 0.42537(14) 0.98798(11) 0.0434(4) Uani 1 1 d . . .
O4 O -0.13775(14) 0.25861(13) 1.11355(11) 0.0345(3) Uani 1 1 d . . .
N1 N 0.23249(15) 0.22752(14) 0.55966(11) 0.0245(3) Uani 1 1 d . . .
C1 C 0.08716(17) 0.06971(17) 0.70371(14) 0.0231(3) Uani 1 1 d . . .
H1 H 0.1284 -0.0160 0.7579 0.028 Uiso 1 1 calc R . .
C2 C -0.07457(18) 0.05331(17) 0.69677(14) 0.0245(3) Uani 1 1 d . . .
H2 H -0.0778 -0.0335 0.6655 0.029 Uiso 1 1 calc R . .
C3 C -0.16066(17) 0.04362(17) 0.82110(14) 0.0241(3) Uani 1 1 d . . .
C4 C -0.16248(17) 0.16928(17) 0.86503(14) 0.0233(3) Uani 1 1 d . . .
C5 C -0.07971(17) 0.28276(17) 0.77569(14) 0.0235(3) Uani 1 1 d . . .
H5 H -0.0864 0.3737 0.8045 0.028 Uiso 1 1 calc R . .
C6 C 0.08369(17) 0.20902(17) 0.74717(13) 0.0232(3) Uani 1 1 d . . .
H6 H 0.1303 0.1868 0.8173 0.028 Uiso 1 1 calc R . .
C7 C -0.13696(18) 0.19218(18) 0.62408(14) 0.0264(3) Uani 1 1 d . . .
H7 H -0.1707 0.1950 0.5549 0.032 Uiso 1 1 calc R . .
C8 C -0.14059(18) 0.30952(18) 0.66506(14) 0.0264(3) Uani 1 1 d . . .
H8 H -0.1784 0.4033 0.6280 0.032 Uiso 1 1 calc R . .
C9 C 0.17308(18) 0.30542(18) 0.64756(14) 0.0248(3) Uani 1 1 d . . .
C10 C 0.18948(18) 0.08865(17) 0.58617(14) 0.0252(3) Uani 1 1 d . . .
C11 C 0.31774(18) 0.28889(17) 0.45119(14) 0.0249(3) Uani 1 1 d . . .
C12 C 0.4522(2) 0.33655(19) 0.44372(15) 0.0301(4) Uani 1 1 d . . .
C13 C 0.5308(2) 0.4061(2) 0.34054(17) 0.0380(4) Uani 1 1 d . . .
H13 H 0.6217 0.4399 0.3381 0.046 Uiso 1 1 calc R . .
C14 C 0.4745(2) 0.4258(2) 0.24065(16) 0.0376(4) Uani 1 1 d . . .
H14 H 0.5277 0.4736 0.1689 0.045 Uiso 1 1 calc R . .
C15 C 0.3421(2) 0.37708(19) 0.24325(15) 0.0343(4) Uani 1 1 d . . .
H15 H 0.3049 0.3890 0.1741 0.041 Uiso 1 1 calc R . .
C16 C 0.26628(19) 0.31105(18) 0.34862(15) 0.0282(4) Uani 1 1 d . . .
C17 C -0.22772(18) -0.07071(18) 0.88922(15) 0.0262(3) Uani 1 1 d . . .
H17 H -0.2235 -0.1548 0.8593 0.031 Uiso 1 1 calc R . .
C18 C -0.30391(18) -0.06551(18) 1.00464(14) 0.0259(3) Uani 1 1 d . . .
C19 C -0.38268(19) -0.17988(19) 1.07427(15) 0.0295(4) Uani 1 1 d . . .
H19 H -0.3825 -0.2627 1.0439 0.035 Uiso 1 1 calc R . .
C20 C -0.45888(19) -0.17282(19) 1.18445(15) 0.0309(4) Uani 1 1 d . . .
H20 H -0.5096 -0.2510 1.2304 0.037 Uiso 1 1 calc R . .
C21 C -0.46204(18) -0.04964(19) 1.22976(15) 0.0300(4) Uani 1 1 d . . .
H21 H -0.5172 -0.0440 1.3055 0.036 Uiso 1 1 calc R . .
C22 C -0.38589(18) 0.06242(19) 1.16502(14) 0.0268(3) Uani 1 1 d . . .
H22 H -0.3880 0.1443 1.1971 0.032 Uiso 1 1 calc R . .
C23 C -0.30403(17) 0.05779(17) 1.05093(14) 0.0238(3) Uani 1 1 d . . .
C24 C -0.22721(17) 0.17456(17) 0.97853(14) 0.0234(3) Uani 1 1 d . . .
C25 C -0.21091(18) 0.30072(18) 1.02558(13) 0.0244(3) Uani 1 1 d . . .
C26 C -0.1017(2) 0.3713(2) 1.15968(18) 0.0404(5) Uani 1 1 d . . .
H26A H -0.0099 0.4062 1.1119 0.061 Uiso 1 1 calc R . .
H26B H -0.0878 0.3326 1.2398 0.061 Uiso 1 1 calc R . .
H26C H -0.1831 0.4516 1.1586 0.061 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 C16 1.353(2) . ?
F2 C12 1.345(2) . ?
O1 C10 1.206(2) . ?
O2 C9 1.205(2) . ?
O3 C25 1.202(2) . ?
O4 C25 1.336(2) . ?
O4 C26 1.446(2) . ?
N1 C9 1.397(2) . ?
N1 C10 1.402(2) . ?
N1 C11 1.420(2) . ?
C1 C10 1.509(2) . ?
C1 C6 1.540(2) . ?
C1 C2 1.564(2) . ?
C1 H1 1.0000 . ?
C2 C7 1.513(2) . ?
C2 C3 1.522(2) . ?
C2 H2 1.0000 . ?
C3 C17 1.360(2) . ?
C3 C4 1.423(2) . ?
C4 C24 1.374(2) . ?
C4 C5 1.518(2) . ?
C5 C8 1.518(2) . ?
C5 C6 1.558(2) . ?
C5 H5 1.0000 . ?
C6 C9 1.511(2) . ?
C6 H6 1.0000 . ?
C7 C8 1.325(2) . ?
C7 H7 0.9500 . ?
C8 H8 0.9500 . ?
C11 C12 1.384(2) . ?
C11 C16 1.385(2) . ?
C12 C13 1.377(3) . ?
C13 C14 1.382(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.385(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.373(2) . ?
C15 H15 0.9500 . ?
C17 C18 1.420(2) . ?
C17 H17 0.9500 . ?
C18 C19 1.419(2) . ?
C18 C23 1.423(2) . ?
C19 C20 1.368(3) . ?
C19 H19 0.9500 . ?
C20 C21 1.408(3) . ?
C20 H20 0.9500 . ?
C21 C22 1.374(2) . ?
C21 H21 0.9500 . ?
C22 C23 1.420(2) . ?
C22 H22 0.9500 . ?
C23 C24 1.437(2) . ?
C24 C25 1.497(2) . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?

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
C25 O4 C26 116.97(14) . . ?
C9 N1 C10 113.23(13) . . ?
C9 N1 C11 122.55(13) . . ?
C10 N1 C11 124.04(13) . . ?
C10 C1 C6 105.23(13) . . ?
C10 C1 C2 112.41(13) . . ?
C6 C1 C2 109.06(13) . . ?
C10 C1 H1 110.0 . . ?
C6 C1 H1 110.0 . . ?
C2 C1 H1 110.0 . . ?
C7 C2 C3 107.74(13) . . ?
C7 C2 C1 107.69(13) . . ?
C3 C2 C1 104.29(12) . . ?
C7 C2 H2 112.2 . . ?
C3 C2 H2 112.2 . . ?
C1 C2 H2 112.2 . . ?
C17 C3 C4 120.65(15) . . ?
C17 C3 C2 126.48(15) . . ?
C4 C3 C2 112.85(14) . . ?
C24 C4 C3 120.36(15) . . ?
C24 C4 C5 127.39(15) . . ?
C3 C4 C5 112.15(14) . . ?
C8 C5 C4 107.81(13) . . ?
C8 C5 C6 106.22(12) . . ?
C4 C5 C6 105.35(13) . . ?
C8 C5 H5 112.3 . . ?
C4 C5 H5 112.3 . . ?
C6 C5 H5 112.3 . . ?
C9 C6 C1 105.26(13) . . ?
C9 C6 C5 110.20(13) . . ?
C1 C6 C5 110.07(12) . . ?
C9 C6 H6 110.4 . . ?
C1 C6 H6 110.4 . . ?
C5 C6 H6 110.4 . . ?
C8 C7 C2 114.30(14) . . ?
C8 C7 H7 122.9 . . ?
C2 C7 H7 122.9 . . ?
C7 C8 C5 114.90(14) . . ?
C7 C8 H8 122.5 . . ?
C5 C8 H8 122.5 . . ?
O2 C9 N1 124.29(15) . . ?
O2 C9 C6 127.68(15) . . ?
N1 C9 C6 108.01(13) . . ?
O1 C10 N1 123.65(15) . . ?
O1 C10 C1 128.33(15) . . ?
N1 C10 C1 108.02(13) . . ?
C12 C11 C16 116.83(15) . . ?
C12 C11 N1 121.60(15) . . ?
C16 C11 N1 121.48(15) . . ?
F2 C12 C13 119.55(16) . . ?
F2 C12 C11 118.08(15) . . ?
C13 C12 C11 122.36(17) . . ?
C12 C13 C14 118.55(18) . . ?
C12 C13 H13 120.7 . . ?
C14 C13 H13 120.7 . . ?
C13 C14 C15 121.21(17) . . ?
C13 C14 H14 119.4 . . ?
C15 C14 H14 119.4 . . ?
C16 C15 C14 118.05(17) . . ?
C16 C15 H15 121.0 . . ?
C14 C15 H15 121.0 . . ?
F1 C16 C15 119.33(16) . . ?
F1 C16 C11 117.66(15) . . ?
C15 C16 C11 122.97(17) . . ?
C3 C17 C18 120.57(15) . . ?
C3 C17 H17 119.7 . . ?
C18 C17 H17 119.7 . . ?
C19 C18 C17 121.28(16) . . ?
C19 C18 C23 119.16(16) . . ?
C17 C18 C23 119.54(15) . . ?
C20 C19 C18 121.06(17) . . ?
C20 C19 H19 119.5 . . ?
C18 C19 H19 119.5 . . ?
C19 C20 C21 120.00(16) . . ?
C19 C20 H20 120.0 . . ?
C21 C20 H20 120.0 . . ?
C22 C21 C20 120.39(16) . . ?
C22 C21 H21 119.8 . . ?
C20 C21 H21 119.8 . . ?
C21 C22 C23 121.07(16) . . ?
C21 C22 H22 119.5 . . ?
C23 C22 H22 119.5 . . ?
C22 C23 C18 118.29(15) . . ?
C22 C23 C24 123.00(15) . . ?
C18 C23 C24 118.65(15) . . ?
C4 C24 C23 120.03(15) . . ?
C4 C24 C25 118.76(14) . . ?
C23 C24 C25 121.18(14) . . ?
O3 C25 O4 123.02(15) . . ?
O3 C25 C24 125.58(15) . . ?
O4 C25 C24 111.35(14) . . ?
O4 C26 H26A 109.5 . . ?
O4 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
O4 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?

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
C10 C1 C2 C7 -62.87(17) . . . . ?
C6 C1 C2 C7 53.43(16) . . . . ?
C10 C1 C2 C3 -177.15(13) . . . . ?
C6 C1 C2 C3 -60.84(16) . . . . ?
C7 C2 C3 C17 128.42(17) . . . . ?
C1 C2 C3 C17 -117.33(17) . . . . ?
C7 C2 C3 C4 -53.39(17) . . . . ?
C1 C2 C3 C4 60.86(17) . . . . ?
C17 C3 C4 C24 2.5(2) . . . . ?
C2 C3 C4 C24 -175.78(14) . . . . ?
C17 C3 C4 C5 179.19(14) . . . . ?
C2 C3 C4 C5 0.89(19) . . . . ?
C24 C4 C5 C8 -131.60(17) . . . . ?
C3 C4 C5 C8 52.02(17) . . . . ?
C24 C4 C5 C6 115.29(17) . . . . ?
C3 C4 C5 C6 -61.09(16) . . . . ?
C10 C1 C6 C9 4.95(16) . . . . ?
C2 C1 C6 C9 -115.85(14) . . . . ?
C10 C1 C6 C5 123.68(13) . . . . ?
C2 C1 C6 C5 2.88(17) . . . . ?
C8 C5 C6 C9 58.65(16) . . . . ?
C4 C5 C6 C9 172.87(12) . . . . ?
C8 C5 C6 C1 -57.01(16) . . . . ?
C4 C5 C6 C1 57.21(16) . . . . ?
C3 C2 C7 C8 53.30(18) . . . . ?
C1 C2 C7 C8 -58.66(18) . . . . ?
C2 C7 C8 C5 0.8(2) . . . . ?
C4 C5 C8 C7 -54.56(18) . . . . ?
C6 C5 C8 C7 57.97(18) . . . . ?
C10 N1 C9 O2 -176.42(16) . . . . ?
C11 N1 C9 O2 -1.2(3) . . . . ?
C10 N1 C9 C6 2.07(18) . . . . ?
C11 N1 C9 C6 177.31(14) . . . . ?
C1 C6 C9 O2 174.04(16) . . . . ?
C5 C6 C9 O2 55.4(2) . . . . ?
C1 C6 C9 N1 -4.38(17) . . . . ?
C5 C6 C9 N1 -123.02(14) . . . . ?
C9 N1 C10 O1 -178.52(16) . . . . ?
C11 N1 C10 O1 6.3(3) . . . . ?
C9 N1 C10 C1 1.24(18) . . . . ?
C11 N1 C10 C1 -173.92(14) . . . . ?
C6 C1 C10 O1 175.84(17) . . . . ?
C2 C1 C10 O1 -65.6(2) . . . . ?
C6 C1 C10 N1 -3.90(17) . . . . ?
C2 C1 C10 N1 114.68(14) . . . . ?
C9 N1 C11 C12 62.9(2) . . . . ?
C10 N1 C11 C12 -122.43(18) . . . . ?
C9 N1 C11 C16 -113.57(18) . . . . ?
C10 N1 C11 C16 61.2(2) . . . . ?
C16 C11 C12 F2 -179.40(14) . . . . ?
N1 C11 C12 F2 4.0(2) . . . . ?
C16 C11 C12 C13 1.6(3) . . . . ?
N1 C11 C12 C13 -174.98(16) . . . . ?
F2 C12 C13 C14 179.47(16) . . . . ?
C11 C12 C13 C14 -1.5(3) . . . . ?
C12 C13 C14 C15 0.0(3) . . . . ?
C13 C14 C15 C16 1.3(3) . . . . ?
C14 C15 C16 F1 176.28(15) . . . . ?
C14 C15 C16 C11 -1.3(3) . . . . ?
C12 C11 C16 F1 -177.74(14) . . . . ?
N1 C11 C16 F1 -1.2(2) . . . . ?
C12 C11 C16 C15 -0.2(3) . . . . ?
N1 C11 C16 C15 176.43(15) . . . . ?
C4 C3 C17 C18 1.5(2) . . . . ?
C2 C3 C17 C18 179.56(15) . . . . ?
C3 C17 C18 C19 175.84(15) . . . . ?
C3 C17 C18 C23 -2.9(2) . . . . ?
C17 C18 C19 C20 -178.43(15) . . . . ?
C23 C18 C19 C20 0.3(2) . . . . ?
C18 C19 C20 C21 1.1(3) . . . . ?
C19 C20 C21 C22 -1.6(3) . . . . ?
C20 C21 C22 C23 0.8(2) . . . . ?
C21 C22 C23 C18 0.6(2) . . . . ?
C21 C22 C23 C24 177.69(15) . . . . ?
C19 C18 C23 C22 -1.1(2) . . . . ?
C17 C18 C23 C22 177.63(14) . . . . ?
C19 C18 C23 C24 -178.36(14) . . . . ?
C17 C18 C23 C24 0.4(2) . . . . ?
C3 C4 C24 C23 -5.0(2) . . . . ?
C5 C4 C24 C23 178.86(14) . . . . ?
C3 C4 C24 C25 172.70(14) . . . . ?
C5 C4 C24 C25 -3.4(2) . . . . ?
C22 C23 C24 C4 -173.55(15) . . . . ?
C18 C23 C24 C4 3.5(2) . . . . ?
C22 C23 C24 C25 8.8(2) . . . . ?
C18 C23 C24 C25 -174.13(14) . . . . ?
C26 O4 C25 O3 -3.2(2) . . . . ?
C26 O4 C25 C24 174.19(14) . . . . ?
C4 C24 C25 O3 59.4(2) . . . . ?
C23 C24 C25 O3 -122.89(19) . . . . ?
C4 C24 C25 O4 -117.88(16) . . . . ?
C23 C24 C25 O4 59.81(19) . . . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.274
_refine_diff_density_min         -0.208
_refine_diff_density_rms         0.045
_database_code_depnum_ccdc_archive 'CCDC 940171'
