# Electronic Supplementary Material (ESI) for ChemComm.
# 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_kp1

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H10 F N3 O'
_chemical_formula_weight         231.23

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                   11.785(2)
_cell_length_b                   5.7638(12)
_cell_length_c                   16.482(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 102.47(3)
_cell_angle_gamma                90.00
_cell_volume                     1093.2(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    108(2)
_cell_measurement_reflns_used    7856
_cell_measurement_theta_min      1.6655
_cell_measurement_theta_max      31.1782

_exptl_crystal_description       Block
_exptl_crystal_colour            Colourless
_exptl_crystal_size_max          0.47
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.24
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.405
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             480
_exptl_absorpt_coefficient_mu    0.105
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9523
_exptl_absorpt_correction_T_max  0.9752
_exptl_absorpt_process_details   CrystalClear

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      108(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  'Rigaku Saturn 724'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8361
_diffrn_reflns_av_R_equivalents  0.0208
_diffrn_reflns_av_sigmaI/netI    0.0148
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         3.54
_diffrn_reflns_theta_max         24.98
_reflns_number_total             1889
_reflns_number_gt                1826
_reflns_threshold_expression     >2sigma(I)

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

_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. All non H ANIS. No solvent
 No disorder. All H calc and Ride except NH protons which were found and
 freely refined
;

_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)+(0.1317P)²+0.3591P] 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         1889
_refine_ls_number_parameters     162
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0523
_refine_ls_R_factor_gt           0.0436
_refine_ls_wR_factor_ref         0.1893
_refine_ls_wR_factor_gt          0.1451
_refine_ls_goodness_of_fit_ref   1.156
_refine_ls_restrained_S_all      1.156
_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
O1 O 0.61337(11) 0.9161(2) 0.08575(8) 0.0241(4) Uani 1 1 d . . .
N1 N 0.36384(13) 0.4003(3) 0.08542(9) 0.0206(4) Uani 1 1 d . . .
N2 N 0.43774(14) 0.7485(3) 0.04323(10) 0.0203(4) Uani 1 1 d . . .
H2X H 0.424(2) 0.851(5) 0.0076(15) 0.032(6) Uiso 1 1 d . . .
N3 N 0.57805(14) 0.5705(3) 0.14509(9) 0.0208(4) Uani 1 1 d . . .
H3X H 0.5216(19) 0.466(4) 0.1402(13) 0.022(5) Uiso 1 1 d . . .
F1 F 0.98839(10) 0.3773(2) 0.36829(7) 0.0321(4) Uani 1 1 d . . .
C1 C 0.27462(16) 0.2522(3) 0.07866(11) 0.0225(5) Uani 1 1 d . . .
H1 H 0.2859 0.1159 0.1119 0.027 Uiso 1 1 calc R . .
C2 C 0.16766(16) 0.2855(3) 0.02651(11) 0.0237(5) Uani 1 1 d . . .
H2 H 0.1067 0.1759 0.0237 0.028 Uiso 1 1 calc R . .
C3 C 0.15198(16) 0.4864(3) -0.02200(11) 0.0242(5) Uani 1 1 d . . .
H3 H 0.0794 0.5154 -0.0587 0.029 Uiso 1 1 calc R . .
C4 C 0.24147(16) 0.6417(3) -0.01670(11) 0.0215(5) Uani 1 1 d . . .
H4 H 0.2322 0.7792 -0.0492 0.026 Uiso 1 1 calc R . .
C5 C 0.34712(16) 0.5911(3) 0.03831(10) 0.0186(5) Uani 1 1 d . . .
C6 C 0.54889(16) 0.7526(3) 0.09238(10) 0.0189(5) Uani 1 1 d . . .
C7 C 0.68564(16) 0.5308(3) 0.19985(10) 0.0189(5) Uani 1 1 d . . .
C8 C 0.77897(16) 0.6847(3) 0.21222(11) 0.0219(5) Uani 1 1 d . . .
H8 H 0.7726 0.8262 0.1820 0.026 Uiso 1 1 calc R . .
C9 C 0.88129(16) 0.6313(4) 0.26870(11) 0.0239(5) Uani 1 1 d . . .
H9 H 0.9452 0.7356 0.2777 0.029 Uiso 1 1 calc R . .
C10 C 0.88849(16) 0.4255(4) 0.31129(11) 0.0232(5) Uani 1 1 d . . .
C11 C 0.79886(18) 0.2674(3) 0.30001(11) 0.0239(5) Uani 1 1 d . . .
H11 H 0.8066 0.1253 0.3299 0.029 Uiso 1 1 calc R . .
C12 C 0.69666(16) 0.3220(3) 0.24349(11) 0.0226(5) Uani 1 1 d . . .
H12 H 0.6336 0.2157 0.2345 0.027 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
O1 C6 1.230(2) . ?
N1 C5 1.336(2) . ?
N1 C1 1.340(2) . ?
N2 C6 1.384(2) . ?
N2 C5 1.390(2) . ?
N2 H2X 0.82(3) . ?
N3 C6 1.359(2) . ?
N3 C7 1.407(2) . ?
N3 H3X 0.89(2) . ?
F1 C10 1.367(2) . ?
C1 C2 1.377(3) . ?
C1 H1 0.9500 . ?
C2 C3 1.396(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.372(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.403(3) . ?
C4 H4 0.9500 . ?
C7 C8 1.393(3) . ?
C7 C12 1.394(3) . ?
C8 C9 1.389(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.372(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.377(3) . ?
C11 C12 1.390(3) . ?
C11 H11 0.9500 . ?
C12 H12 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
C5 N1 C1 117.49(16) . . ?
C6 N2 C5 131.56(16) . . ?
C6 N2 H2X 115.1(17) . . ?
C5 N2 H2X 113.1(17) . . ?
C6 N3 C7 127.17(16) . . ?
C6 N3 H3X 112.6(14) . . ?
C7 N3 H3X 120.1(14) . . ?
N1 C1 C2 123.97(17) . . ?
N1 C1 H1 118.0 . . ?
C2 C1 H1 118.0 . . ?
C1 C2 C3 117.60(17) . . ?
C1 C2 H2 121.2 . . ?
C3 C2 H2 121.2 . . ?
C4 C3 C2 119.98(17) . . ?
C4 C3 H3 120.0 . . ?
C2 C3 H3 120.0 . . ?
C3 C4 C5 117.93(17) . . ?
C3 C4 H4 121.0 . . ?
C5 C4 H4 121.0 . . ?
N1 C5 N2 119.22(16) . . ?
N1 C5 C4 123.04(17) . . ?
N2 C5 C4 117.74(16) . . ?
O1 C6 N3 124.95(17) . . ?
O1 C6 N2 119.06(16) . . ?
N3 C6 N2 115.99(16) . . ?
C8 C7 C12 119.45(17) . . ?
C8 C7 N3 124.32(17) . . ?
C12 C7 N3 116.22(16) . . ?
C9 C8 C7 120.02(18) . . ?
C9 C8 H8 120.0 . . ?
C7 C8 H8 120.0 . . ?
C10 C9 C8 118.90(18) . . ?
C10 C9 H9 120.5 . . ?
C8 C9 H9 120.5 . . ?
F1 C10 C9 118.46(18) . . ?
F1 C10 C11 118.68(17) . . ?
C9 C10 C11 122.85(18) . . ?
C10 C11 C12 117.96(17) . . ?
C10 C11 H11 121.0 . . ?
C12 C11 H11 121.0 . . ?
C11 C12 C7 120.80(18) . . ?
C11 C12 H12 119.6 . . ?
C7 C12 H12 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
C5 N1 C1 C2 -0.1(3) . . . . ?
N1 C1 C2 C3 0.0(3) . . . . ?
C1 C2 C3 C4 0.1(3) . . . . ?
C2 C3 C4 C5 0.0(3) . . . . ?
C1 N1 C5 N2 -179.68(15) . . . . ?
C1 N1 C5 C4 0.2(3) . . . . ?
C6 N2 C5 N1 -2.5(3) . . . . ?
C6 N2 C5 C4 177.53(17) . . . . ?
C3 C4 C5 N1 -0.2(3) . . . . ?
C3 C4 C5 N2 179.73(15) . . . . ?
C7 N3 C6 O1 -1.5(3) . . . . ?
C7 N3 C6 N2 178.46(15) . . . . ?
C5 N2 C6 O1 -178.87(17) . . . . ?
C5 N2 C6 N3 1.2(3) . . . . ?
C6 N3 C7 C8 4.3(3) . . . . ?
C6 N3 C7 C12 -175.62(16) . . . . ?
C12 C7 C8 C9 -1.1(3) . . . . ?
N3 C7 C8 C9 179.04(16) . . . . ?
C7 C8 C9 C10 0.3(3) . . . . ?
C8 C9 C10 F1 -178.32(15) . . . . ?
C8 C9 C10 C11 0.7(3) . . . . ?
F1 C10 C11 C12 178.24(15) . . . . ?
C9 C10 C11 C12 -0.7(3) . . . . ?
C10 C11 C12 C7 -0.1(3) . . . . ?
C8 C7 C12 C11 1.0(3) . . . . ?
N3 C7 C12 C11 -179.11(15) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H2X O1 0.82(3) 2.02(3) 2.840(2) 176(2) 3_675
N3 H3X N1 0.89(2) 1.92(2) 2.689(2) 143.8(19) .

_diffrn_measured_fraction_theta_max 0.981
_diffrn_reflns_theta_full        24.98
_diffrn_measured_fraction_theta_full 0.981
_refine_diff_density_max         0.451
_refine_diff_density_min         -0.417
_refine_diff_density_rms         0.119
_database_code_depnum_ccdc_archive 'CCDC 1002407'
#######################################################################
#
#                 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_kp2

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H9 F2 N3 O'
_chemical_formula_weight         249.22

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           ?
_symmetry_space_group_name_H-M   ?

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

_cell_length_a                   10.484(2)
_cell_length_b                   5.4019(11)
_cell_length_c                   19.491(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 104.37(3)
_cell_angle_gamma                90.00
_cell_volume                     1069.3(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.548
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             512
_exptl_absorpt_coefficient_mu    0.126
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            11879
_diffrn_reflns_av_R_equivalents  0.0251
_diffrn_reflns_av_sigmaI/netI    0.0222
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         2.03
_diffrn_reflns_theta_max         31.23
_reflns_number_total             3114
_reflns_number_gt                3021
_reflns_threshold_expression     >2sigma(I)

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

_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)+(0.1298P)²+0.4488P] 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         3114
_refine_ls_number_parameters     163
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0608
_refine_ls_R_factor_gt           0.0547
_refine_ls_wR_factor_ref         0.2188
_refine_ls_wR_factor_gt          0.1935
_refine_ls_goodness_of_fit_ref   1.180
_refine_ls_restrained_S_all      1.180
_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 1.22958(11) 0.5922(2) 1.20051(6) 0.0336(3) Uani 1 1 d . . .
F2 F 0.89228(10) 0.8208(2) 1.00313(5) 0.0266(3) Uani 1 1 d . . .
O1 O 0.66064(12) 0.0878(2) 1.05635(6) 0.0233(3) Uani 1 1 d . . .
N1 N 0.59388(14) 0.6173(3) 0.89394(7) 0.0227(3) Uani 1 1 d . . .
N2 N 0.54448(13) 0.2652(3) 0.95489(7) 0.0206(3) Uani 1 1 d . . .
H2X H 0.4828 0.1260 0.9530 0.025 Uiso 1 1 d . . .
N3 N 0.74421(13) 0.4355(3) 1.01512(7) 0.0210(3) Uani 1 1 d . . .
H3X H 0.7234 0.5468 0.9810 0.025 Uiso 1 1 d . . .
C1 C 0.56177(17) 0.7641(3) 0.83666(9) 0.0250(4) Uani 1 1 d . . .
H1 H 0.6165 0.8975 0.8341 0.030 Uiso 1 1 calc R . .
C2 C 0.45212(17) 0.7281(4) 0.78140(9) 0.0262(4) Uani 1 1 d . . .
H2 H 0.4339 0.8333 0.7424 0.031 Uiso 1 1 calc R . .
C3 C 0.36927(17) 0.5296(4) 0.78566(9) 0.0260(4) Uani 1 1 d . . .
H3 H 0.2941 0.5015 0.7495 0.031 Uiso 1 1 calc R . .
C4 C 0.39965(16) 0.3751(3) 0.84399(8) 0.0229(3) Uani 1 1 d . . .
H4 H 0.3458 0.2419 0.8480 0.028 Uiso 1 1 calc R . .
C5 C 0.51443(15) 0.4256(3) 0.89707(8) 0.0192(3) Uani 1 1 d . . .
C6 C 0.65300(14) 0.2543(3) 1.01195(7) 0.0182(3) Uani 1 1 d . . .
C7 C 0.86524(15) 0.4588(3) 1.06525(8) 0.0189(3) Uani 1 1 d . . .
C8 C 0.91758(16) 0.2950(3) 1.12038(8) 0.0227(3) Uani 1 1 d . . .
H8 H 0.8696 0.1561 1.1270 0.027 Uiso 1 1 calc R . .
C9 C 1.04149(16) 0.3378(3) 1.16564(9) 0.0246(4) Uani 1 1 d . . .
H9 H 1.0765 0.2280 1.2022 0.029 Uiso 1 1 calc R . .
C10 C 1.11124(16) 0.5451(3) 1.15537(9) 0.0238(4) Uani 1 1 d . . .
C11 C 1.06445(16) 0.7118(3) 1.10122(9) 0.0240(4) Uani 1 1 d . . .
H11 H 1.1132 0.8496 1.0946 0.029 Uiso 1 1 calc R . .
C12 C 0.94165(15) 0.6639(3) 1.05730(8) 0.0210(3) 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 C10 1.3551(18) . ?
F2 C12 1.3530(19) . ?
O1 C6 1.2372(19) . ?
N1 C5 1.340(2) . ?
N1 C1 1.342(2) . ?
N2 C6 1.3807(19) . ?
N2 C5 1.3944(19) . ?
N2 H2X 0.9865 . ?
N3 C6 1.359(2) . ?
N3 C7 1.4018(19) . ?
N3 H3X 0.8827 . ?
C1 C2 1.380(2) . ?
C1 H1 0.9300 . ?
C2 C3 1.395(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.382(2) . ?
C3 H3 0.9300 . ?
C4 C5 1.405(2) . ?
C4 H4 0.9300 . ?
C7 C8 1.395(2) . ?
C7 C12 1.398(2) . ?
C8 C9 1.397(2) . ?
C8 H8 0.9300 . ?
C9 C10 1.379(3) . ?
C9 H9 0.9300 . ?
C10 C11 1.381(3) . ?
C11 C12 1.382(2) . ?
C11 H11 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
C5 N1 C1 117.64(14) . . ?
C6 N2 C5 130.78(13) . . ?
C6 N2 H2X 113.5 . . ?
C5 N2 H2X 115.4 . . ?
C6 N3 C7 126.96(13) . . ?
C6 N3 H3X 114.6 . . ?
C7 N3 H3X 118.4 . . ?
N1 C1 C2 123.66(16) . . ?
N1 C1 H1 118.2 . . ?
C2 C1 H1 118.2 . . ?
C1 C2 C3 118.17(15) . . ?
C1 C2 H2 120.9 . . ?
C3 C2 H2 120.9 . . ?
C4 C3 C2 119.54(16) . . ?
C4 C3 H3 120.2 . . ?
C2 C3 H3 120.2 . . ?
C3 C4 C5 117.95(16) . . ?
C3 C4 H4 121.0 . . ?
C5 C4 H4 121.0 . . ?
N1 C5 N2 119.93(14) . . ?
N1 C5 C4 123.02(14) . . ?
N2 C5 C4 117.05(14) . . ?
O1 C6 N3 124.70(14) . . ?
O1 C6 N2 119.45(14) . . ?
N3 C6 N2 115.83(13) . . ?
C8 C7 C12 117.48(14) . . ?
C8 C7 N3 126.51(15) . . ?
C12 C7 N3 115.99(14) . . ?
C7 C8 C9 120.51(16) . . ?
C7 C8 H8 119.7 . . ?
C9 C8 H8 119.7 . . ?
C10 C9 C8 119.11(16) . . ?
C10 C9 H9 120.4 . . ?
C8 C9 H9 120.4 . . ?
F1 C10 C9 119.42(16) . . ?
F1 C10 C11 117.91(16) . . ?
C9 C10 C11 122.66(15) . . ?
C10 C11 C12 116.79(16) . . ?
C10 C11 H11 121.6 . . ?
C12 C11 H11 121.6 . . ?
F2 C12 C11 118.88(15) . . ?
F2 C12 C7 117.67(14) . . ?
C11 C12 C7 123.44(15) . . ?

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
C5 N1 C1 C2 0.1(3) . . . . ?
N1 C1 C2 C3 0.7(3) . . . . ?
C1 C2 C3 C4 -0.6(3) . . . . ?
C2 C3 C4 C5 -0.1(3) . . . . ?
C1 N1 C5 N2 178.97(14) . . . . ?
C1 N1 C5 C4 -0.9(2) . . . . ?
C6 N2 C5 N1 -5.2(3) . . . . ?
C6 N2 C5 C4 174.67(16) . . . . ?
C3 C4 C5 N1 0.9(3) . . . . ?
C3 C4 C5 N2 -178.95(15) . . . . ?
C7 N3 C6 O1 4.5(3) . . . . ?
C7 N3 C6 N2 -176.54(14) . . . . ?
C5 N2 C6 O1 -177.42(15) . . . . ?
C5 N2 C6 N3 3.5(2) . . . . ?
C6 N3 C7 C8 2.4(3) . . . . ?
C6 N3 C7 C12 -179.59(15) . . . . ?
C12 C7 C8 C9 0.3(2) . . . . ?
N3 C7 C8 C9 178.36(15) . . . . ?
C7 C8 C9 C10 0.3(2) . . . . ?
C8 C9 C10 F1 177.82(14) . . . . ?
C8 C9 C10 C11 -1.0(3) . . . . ?
F1 C10 C11 C12 -177.96(14) . . . . ?
C9 C10 C11 C12 0.9(2) . . . . ?
C10 C11 C12 F2 -179.40(14) . . . . ?
C10 C11 C12 C7 -0.1(2) . . . . ?
C8 C7 C12 F2 178.84(13) . . . . ?
N3 C7 C12 F2 0.6(2) . . . . ?
C8 C7 C12 C11 -0.5(2) . . . . ?
N3 C7 C12 C11 -178.69(14) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H2X O1 0.99 1.87 2.8415(18) 168.2 3_657
N3 H3X N1 0.88 1.93 2.679(2) 141.7 .

_diffrn_measured_fraction_theta_max 0.896
_diffrn_reflns_theta_full        31.23
_diffrn_measured_fraction_theta_full 0.896
_refine_diff_density_max         0.351
_refine_diff_density_min         -0.428
_refine_diff_density_rms         0.106
_database_code_depnum_ccdc_archive 'CCDC 1002408'
#######################################################################
#
#                 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_kp3

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H10 N4 O3'
_chemical_formula_weight         258.24

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'

_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                   6.9066(14)
_cell_length_b                   7.9420(16)
_cell_length_c                   11.370(2)
_cell_angle_alpha                81.16(3)
_cell_angle_beta                 87.98(3)
_cell_angle_gamma                67.14(3)
_cell_volume                     567.6(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    119(2)
_cell_measurement_reflns_used    2056
_cell_measurement_theta_min      1.8132
_cell_measurement_theta_max      31.2237

_exptl_crystal_description       Block
_exptl_crystal_colour            Colourless
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.19
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.511
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             268
_exptl_absorpt_coefficient_mu    0.113
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.7807
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   Crystalclear

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      119(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  'Rigaku Saturn 724'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5674
_diffrn_reflns_av_R_equivalents  0.0379
_diffrn_reflns_av_sigmaI/netI    0.0291
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         1.81
_diffrn_reflns_theta_max         24.00
_reflns_number_total             1686
_reflns_number_gt                1586
_reflns_threshold_expression     >2sigma(I)

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

_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)+(0.1500P)²+0.1082P] 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         1686
_refine_ls_number_parameters     172
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0665
_refine_ls_R_factor_gt           0.0517
_refine_ls_wR_factor_ref         0.2154
_refine_ls_wR_factor_gt          0.1614
_refine_ls_goodness_of_fit_ref   1.241
_refine_ls_restrained_S_all      1.241
_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
O1 O 0.4345(3) 0.0164(2) 0.14909(14) 0.0273(6) Uani 1 1 d . . .
O2 O 0.1455(3) 0.6569(2) 0.24811(14) 0.0311(6) Uani 1 1 d . . .
O3 O 0.3039(3) 0.6544(2) 0.40969(16) 0.0344(6) Uani 1 1 d . . .
N1 N 0.2082(3) 0.5726(3) 0.00214(18) 0.0262(6) Uani 1 1 d . . .
N2 N 0.3536(3) 0.2535(3) -0.00291(17) 0.0228(6) Uani 1 1 d . . .
H2X H 0.4231 0.1560 -0.0478 0.050 Uiso 1 1 d . . .
N3 N 0.2595(3) 0.3120(3) 0.19018(17) 0.0223(6) Uani 1 1 d . . .
H3X H 0.2262 0.4279 0.1571 0.050 Uiso 1 1 d . . .
N4 N 0.2321(3) 0.5794(3) 0.34606(17) 0.0255(6) Uani 1 1 d . . .
C1 C 0.1563(4) 0.7456(3) -0.0549(2) 0.0278(7) Uani 1 1 d . . .
H1 H 0.0975 0.8443 -0.0100 0.033 Uiso 1 1 calc R . .
C2 C 0.1830(4) 0.7887(4) -0.1748(2) 0.0284(7) Uani 1 1 d . . .
H2 H 0.1424 0.9135 -0.2119 0.034 Uiso 1 1 calc R . .
C3 C 0.2720(4) 0.6425(4) -0.2396(2) 0.0286(7) Uani 1 1 d . . .
H3 H 0.2939 0.6663 -0.3224 0.034 Uiso 1 1 calc R . .
C4 C 0.3277(4) 0.4638(4) -0.1829(2) 0.0246(6) Uani 1 1 d . . .
H4 H 0.3881 0.3624 -0.2256 0.029 Uiso 1 1 calc R . .
C5 C 0.2933(4) 0.4348(3) -0.0609(2) 0.0212(6) Uani 1 1 d . . .
C6 C 0.3524(4) 0.1843(3) 0.1166(2) 0.0220(6) Uani 1 1 d . . .
C7 C 0.2482(3) 0.2679(3) 0.3142(2) 0.0203(6) Uani 1 1 d . . .
C8 C 0.2419(3) 0.0992(3) 0.3678(2) 0.0226(6) Uani 1 1 d . . .
H8 H 0.2412 0.0120 0.3193 0.027 Uiso 1 1 calc R . .
C9 C 0.2365(3) 0.0577(3) 0.4902(2) 0.0242(6) Uani 1 1 d . . .
H9 H 0.2306 -0.0571 0.5243 0.029 Uiso 1 1 calc R . .
C10 C 0.2397(4) 0.1801(3) 0.5646(2) 0.0250(6) Uani 1 1 d . . .
H10 H 0.2395 0.1487 0.6487 0.030 Uiso 1 1 calc R . .
C11 C 0.2432(4) 0.3478(3) 0.5141(2) 0.0244(6) Uani 1 1 d . . .
H11 H 0.2456 0.4331 0.5635 0.029 Uiso 1 1 calc R . .
C12 C 0.2433(3) 0.3932(3) 0.3907(2) 0.0208(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
O1 C6 1.230(3) . ?
O2 N4 1.236(3) . ?
O3 N4 1.229(3) . ?
N1 C5 1.330(3) . ?
N1 C1 1.340(3) . ?
N2 C6 1.386(3) . ?
N2 C5 1.394(3) . ?
N2 H2X 0.9516 . ?
N3 C6 1.363(3) . ?
N3 C7 1.406(3) . ?
N3 H3X 0.8813 . ?
N4 C12 1.461(3) . ?
C1 C2 1.377(4) . ?
C1 H1 0.9500 . ?
C2 C3 1.395(4) . ?
C2 H2 0.9500 . ?
C3 C4 1.374(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.398(3) . ?
C4 H4 0.9500 . ?
C7 C8 1.400(3) . ?
C7 C12 1.409(3) . ?
C8 C9 1.383(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.390(4) . ?
C9 H9 0.9500 . ?
C10 C11 1.376(4) . ?
C10 H10 0.9500 . ?
C11 C12 1.394(3) . ?
C11 H11 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
C5 N1 C1 117.7(2) . . ?
C6 N2 C5 130.8(2) . . ?
C6 N2 H2X 110.8 . . ?
C5 N2 H2X 118.0 . . ?
C6 N3 C7 124.02(19) . . ?
C6 N3 H3X 115.0 . . ?
C7 N3 H3X 120.1 . . ?
O3 N4 O2 122.9(2) . . ?
O3 N4 C12 118.2(2) . . ?
O2 N4 C12 118.85(19) . . ?
N1 C1 C2 124.0(2) . . ?
N1 C1 H1 118.0 . . ?
C2 C1 H1 118.0 . . ?
C1 C2 C3 117.5(2) . . ?
C1 C2 H2 121.2 . . ?
C3 C2 H2 121.2 . . ?
C4 C3 C2 119.6(2) . . ?
C4 C3 H3 120.2 . . ?
C2 C3 H3 120.2 . . ?
C3 C4 C5 118.4(2) . . ?
C3 C4 H4 120.8 . . ?
C5 C4 H4 120.8 . . ?
N1 C5 N2 118.8(2) . . ?
N1 C5 C4 122.8(2) . . ?
N2 C5 C4 118.4(2) . . ?
O1 C6 N3 124.8(2) . . ?
O1 C6 N2 119.2(2) . . ?
N3 C6 N2 116.1(2) . . ?
C8 C7 N3 122.3(2) . . ?
C8 C7 C12 116.8(2) . . ?
N3 C7 C12 121.0(2) . . ?
C9 C8 C7 120.9(2) . . ?
C9 C8 H8 119.5 . . ?
C7 C8 H8 119.5 . . ?
C8 C9 C10 121.5(2) . . ?
C8 C9 H9 119.2 . . ?
C10 C9 H9 119.2 . . ?
C11 C10 C9 118.6(2) . . ?
C11 C10 H10 120.7 . . ?
C9 C10 H10 120.7 . . ?
C10 C11 C12 120.4(2) . . ?
C10 C11 H11 119.8 . . ?
C12 C11 H11 119.8 . . ?
C11 C12 C7 121.6(2) . . ?
C11 C12 N4 116.0(2) . . ?
C7 C12 N4 122.4(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
C5 N1 C1 C2 1.0(4) . . . . ?
N1 C1 C2 C3 -0.8(4) . . . . ?
C1 C2 C3 C4 0.4(4) . . . . ?
C2 C3 C4 C5 -0.2(4) . . . . ?
C1 N1 C5 N2 178.4(2) . . . . ?
C1 N1 C5 C4 -0.7(4) . . . . ?
C6 N2 C5 N1 -4.3(4) . . . . ?
C6 N2 C5 C4 174.9(2) . . . . ?
C3 C4 C5 N1 0.4(4) . . . . ?
C3 C4 C5 N2 -178.8(2) . . . . ?
C7 N3 C6 O1 1.0(4) . . . . ?
C7 N3 C6 N2 -178.3(2) . . . . ?
C5 N2 C6 O1 -172.3(2) . . . . ?
C5 N2 C6 N3 7.0(4) . . . . ?
C6 N3 C7 C8 -29.4(3) . . . . ?
C6 N3 C7 C12 150.4(2) . . . . ?
N3 C7 C8 C9 178.22(19) . . . . ?
C12 C7 C8 C9 -1.6(3) . . . . ?
C7 C8 C9 C10 -0.8(3) . . . . ?
C8 C9 C10 C11 1.6(3) . . . . ?
C9 C10 C11 C12 0.1(4) . . . . ?
C10 C11 C12 C7 -2.5(4) . . . . ?
C10 C11 C12 N4 175.80(19) . . . . ?
C8 C7 C12 C11 3.3(3) . . . . ?
N3 C7 C12 C11 -176.6(2) . . . . ?
C8 C7 C12 N4 -175.0(2) . . . . ?
N3 C7 C12 N4 5.2(3) . . . . ?
O3 N4 C12 C11 28.1(3) . . . . ?
O2 N4 C12 C11 -149.7(2) . . . . ?
O3 N4 C12 C7 -153.6(2) . . . . ?
O2 N4 C12 C7 28.6(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H2X O1 0.95 1.88 2.826(3) 173.6 2_655
N3 H3X N1 0.88 1.93 2.665(3) 140.0 .
N3 H3X O2 0.88 2.11 2.720(3) 126.0 .

_diffrn_measured_fraction_theta_max 0.953
_diffrn_reflns_theta_full        24.00
_diffrn_measured_fraction_theta_full 0.953
_refine_diff_density_max         0.591
_refine_diff_density_min         -0.567
_refine_diff_density_rms         0.165
_database_code_depnum_ccdc_archive 'CCDC 1002409'
#######################################################################
#
#                 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_kp5

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H10 F N3 O'
_chemical_formula_sum            'C12 H10 F N3 O'
_chemical_formula_weight         231.23

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   'P n'
_symmetry_space_group_name_Hall  'P -2yac'

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

_cell_length_a                   4.5349(9)
_cell_length_b                   11.591(2)
_cell_length_c                   10.686(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 98.22(3)
_cell_angle_gamma                90.00
_cell_volume                     555.92(19)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.381
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             240
_exptl_absorpt_coefficient_mu    0.103
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            3969
_diffrn_reflns_av_R_equivalents  0.0353
_diffrn_reflns_av_sigmaI/netI    0.0356
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.61
_diffrn_reflns_theta_max         24.98
_reflns_number_total             1764
_reflns_number_gt                1696
_reflns_threshold_expression     >2sigma(I)

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

_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)+(0.2000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.04(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   2(2)
_refine_ls_number_reflns         1764
_refine_ls_number_parameters     155
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0825
_refine_ls_R_factor_gt           0.0774
_refine_ls_wR_factor_ref         0.2670
_refine_ls_wR_factor_gt          0.2479
_refine_ls_goodness_of_fit_ref   1.211
_refine_ls_restrained_S_all      1.211
_refine_ls_shift/su_max          0.016
_refine_ls_shift/su_mean         0.001

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
N2 N 0.0436(10) 0.5686(3) 1.0376(4) 0.0395(10) Uani 1 1 d . . .
H2X H 0.0154 0.5854 1.1321 0.047 Uiso 1 1 d . . .
N3 N 0.3716(9) 0.7205(3) 1.0595(4) 0.0391(10) Uani 1 1 d . . .
H3X H 0.3711 0.7250 1.1655 0.047 Uiso 1 1 d . . .
F1 F 1.1085(8) 1.0850(3) 0.9661(4) 0.0578(10) Uani 1 1 d . . .
C7 C 0.5595(11) 0.8117(4) 1.0293(5) 0.0366(11) Uani 1 1 d . . .
C6 C 0.2238(11) 0.6406(4) 0.9773(5) 0.0358(11) Uani 1 1 d . . .
C12 C 0.6380(13) 0.8955(5) 1.1237(5) 0.0462(13) Uani 1 1 d . . .
H12 H 0.5639 0.8900 1.2003 0.055 Uiso 1 1 calc R . .
C11 C 0.8242(12) 0.9858(4) 1.1035(5) 0.0467(13) Uani 1 1 d . . .
H11 H 0.8805 1.0400 1.1666 0.056 Uiso 1 1 calc R . .
C3 C -0.2502(12) 0.4011(5) 1.0683(5) 0.0442(13) Uani 1 1 d . . .
H3 H -0.2261 0.4173 1.1544 0.053 Uiso 1 1 calc R . .
O1 O 0.2547(9) 0.6323(4) 0.8651(3) 0.0497(10) Uani 1 1 d . . .
C1 C -0.4410(13) 0.2812(4) 0.8920(5) 0.0438(12) Uani 1 1 d . . .
H1 H -0.5449 0.2157 0.8608 0.053 Uiso 1 1 calc R . .
C9 C 0.8470(12) 0.9126(5) 0.8940(5) 0.0474(13) Uani 1 1 d . . .
H9 H 0.9155 0.9206 0.8164 0.057 Uiso 1 1 calc R . .
N1 N -0.3182(10) 0.3499(3) 0.8110(4) 0.0420(10) Uani 1 1 d . . .
C4 C -0.1191(11) 0.4726(4) 0.9856(4) 0.0379(11) Uani 1 1 d . . .
C8 C 0.6703(12) 0.8198(5) 0.9132(4) 0.0419(12) Uani 1 1 d . . .
H8 H 0.6250 0.7639 0.8511 0.050 Uiso 1 1 calc R . .
C5 C -0.1576(12) 0.4416(5) 0.8587(4) 0.0451(13) Uani 1 1 d . . .
H5 H -0.0668 0.4869 0.8034 0.054 Uiso 1 1 calc R . .
C2 C -0.4162(14) 0.3058(5) 1.0207(5) 0.0498(14) Uani 1 1 d . . .
H2 H -0.5094 0.2591 1.0741 0.060 Uiso 1 1 calc R . .
C10 C 0.9259(10) 0.9944(4) 0.9873(5) 0.0418(12) 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
N2 C6 1.389(7) . ?
N2 C4 1.405(6) . ?
N2 H2X 1.0542 . ?
N3 C6 1.382(6) . ?
N3 C7 1.424(6) . ?
N3 H3X 1.1344 . ?
F1 C10 1.376(6) . ?
C7 C8 1.407(7) . ?
C7 C12 1.409(7) . ?
C6 O1 1.231(6) . ?
C12 C11 1.381(8) . ?
C12 H12 0.9300 . ?
C11 C10 1.388(8) . ?
C11 H11 0.9300 . ?
C3 C2 1.391(8) . ?
C3 C4 1.405(7) . ?
C3 H3 0.9300 . ?
C1 N1 1.354(7) . ?
C1 C2 1.394(7) . ?
C1 H1 0.9300 . ?
C9 C8 1.374(8) . ?
C9 C10 1.386(8) . ?
C9 H9 0.9300 . ?
N1 C5 1.346(7) . ?
C4 C5 1.389(6) . ?
C8 H8 0.9300 . ?
C5 H5 0.9300 . ?
C2 H2 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
C6 N2 C4 127.1(4) . . ?
C6 N2 H2X 119.6 . . ?
C4 N2 H2X 113.3 . . ?
C6 N3 C7 127.3(4) . . ?
C6 N3 H3X 126.6 . . ?
C7 N3 H3X 106.2 . . ?
C8 C7 C12 120.0(5) . . ?
C8 C7 N3 123.4(5) . . ?
C12 C7 N3 116.6(5) . . ?
O1 C6 N3 124.0(4) . . ?
O1 C6 N2 124.1(4) . . ?
N3 C6 N2 111.8(4) . . ?
C11 C12 C7 120.6(5) . . ?
C11 C12 H12 119.7 . . ?
C7 C12 H12 119.7 . . ?
C12 C11 C10 118.9(5) . . ?
C12 C11 H11 120.6 . . ?
C10 C11 H11 120.6 . . ?
C2 C3 C4 119.6(5) . . ?
C2 C3 H3 120.2 . . ?
C4 C3 H3 120.2 . . ?
N1 C1 C2 121.9(5) . . ?
N1 C1 H1 119.1 . . ?
C2 C1 H1 119.1 . . ?
C8 C9 C10 121.6(5) . . ?
C8 C9 H9 119.2 . . ?
C10 C9 H9 119.2 . . ?
C5 N1 C1 118.1(4) . . ?
C5 C4 C3 117.1(5) . . ?
C5 C4 N2 125.2(5) . . ?
C3 C4 N2 117.6(4) . . ?
C9 C8 C7 118.3(5) . . ?
C9 C8 H8 120.9 . . ?
C7 C8 H8 120.9 . . ?
N1 C5 C4 124.1(5) . . ?
N1 C5 H5 118.0 . . ?
C4 C5 H5 118.0 . . ?
C3 C2 C1 119.1(5) . . ?
C3 C2 H2 120.5 . . ?
C1 C2 H2 120.5 . . ?
F1 C10 C9 120.2(5) . . ?
F1 C10 C11 119.1(5) . . ?
C9 C10 C11 120.7(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
C6 N3 C7 C8 -13.2(8) . . . . ?
C6 N3 C7 C12 167.9(5) . . . . ?
C7 N3 C6 O1 6.0(8) . . . . ?
C7 N3 C6 N2 -175.9(4) . . . . ?
C4 N2 C6 O1 3.5(8) . . . . ?
C4 N2 C6 N3 -174.7(4) . . . . ?
C8 C7 C12 C11 -0.2(8) . . . . ?
N3 C7 C12 C11 178.8(5) . . . . ?
C7 C12 C11 C10 1.8(8) . . . . ?
C2 C1 N1 C5 2.9(8) . . . . ?
C2 C3 C4 C5 -1.7(8) . . . . ?
C2 C3 C4 N2 179.3(5) . . . . ?
C6 N2 C4 C5 -8.6(8) . . . . ?
C6 N2 C4 C3 170.3(5) . . . . ?
C10 C9 C8 C7 2.5(8) . . . . ?
C12 C7 C8 C9 -1.9(8) . . . . ?
N3 C7 C8 C9 179.2(4) . . . . ?
C1 N1 C5 C4 -2.5(8) . . . . ?
C3 C4 C5 N1 2.0(8) . . . . ?
N2 C4 C5 N1 -179.1(5) . . . . ?
C4 C3 C2 C1 2.1(9) . . . . ?
N1 C1 C2 C3 -2.7(9) . . . . ?
C8 C9 C10 F1 178.6(5) . . . . ?
C8 C9 C10 C11 -0.9(8) . . . . ?
C12 C11 C10 F1 179.2(4) . . . . ?
C12 C11 C10 C9 -1.3(8) . . . . ?

_diffrn_measured_fraction_theta_max 0.986
_diffrn_reflns_theta_full        24.98
_diffrn_measured_fraction_theta_full 0.986
_refine_diff_density_max         0.395
_refine_diff_density_min         -0.341
_refine_diff_density_rms         0.094
_database_code_depnum_ccdc_archive 'CCDC 1002410'
#######################################################################
#
#                 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_kp6

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H9 F2 N3 O'
_chemical_formula_sum            'C12 H9 F2 N3 O'
_chemical_formula_weight         249.22

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   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'

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                   3.7683(8)
_cell_length_b                   27.238(5)
_cell_length_c                   10.409(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 97.29(3)
_cell_angle_gamma                90.00
_cell_volume                     1059.8(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.562
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             512
_exptl_absorpt_coefficient_mu    0.128
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            3844
_diffrn_reflns_av_R_equivalents  0.0300
_diffrn_reflns_av_sigmaI/netI    0.0381
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       3
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_theta_min         1.50
_diffrn_reflns_theta_max         25.00
_reflns_number_total             1819
_reflns_number_gt                1690
_reflns_threshold_expression     >2sigma(I)

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

_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)+(0.1408P)²+0.7341P] 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         1819
_refine_ls_number_parameters     163
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0840
_refine_ls_R_factor_gt           0.0587
_refine_ls_wR_factor_ref         0.2471
_refine_ls_wR_factor_gt          0.1948
_refine_ls_goodness_of_fit_ref   1.290
_refine_ls_restrained_S_all      1.290
_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 0.7294(6) 0.45899(8) 0.8251(2) 0.0308(6) Uani 1 1 d . . .
F2 F 0.1003(6) 0.56654(7) 0.52372(18) 0.0255(6) Uani 1 1 d . . .
O1 O 0.2288(7) 0.68318(9) 0.8825(2) 0.0246(7) Uani 1 1 d . . .
N1 N -0.1941(8) 0.82071(11) 0.9238(3) 0.0221(7) Uani 1 1 d . . .
N2 N -0.0816(8) 0.71767(10) 0.7009(2) 0.0188(7) Uani 1 1 d . . .
H2X H -0.1832 0.7068 0.6162 0.023 Uiso 1 1 d . . .
N3 N 0.1786(7) 0.64274(10) 0.6875(2) 0.0184(7) Uani 1 1 d . . .
H3X H 0.0748 0.6445 0.6099 0.022 Uiso 1 1 d . . .
C1 C -0.3719(9) 0.85201(13) 0.8409(3) 0.0209(8) Uani 1 1 d . . .
H1 H -0.4407 0.8822 0.8718 0.025 Uiso 1 1 calc R . .
C2 C -0.4587(9) 0.84136(13) 0.7103(3) 0.0215(8) Uani 1 1 d . . .
H2 H -0.5822 0.8641 0.6548 0.026 Uiso 1 1 calc R . .
C3 C -0.3597(9) 0.79683(12) 0.6640(3) 0.0186(8) Uani 1 1 d . . .
H3 H -0.4135 0.7892 0.5766 0.022 Uiso 1 1 calc R . .
C4 C -0.1773(8) 0.76316(12) 0.7496(3) 0.0155(7) Uani 1 1 d . . .
C5 C -0.0964(9) 0.77724(13) 0.8791(3) 0.0195(8) Uani 1 1 d . . .
H5 H 0.0306 0.7555 0.9367 0.023 Uiso 1 1 calc R . .
C6 C 0.1173(9) 0.68129(12) 0.7670(3) 0.0181(8) Uani 1 1 d . . .
C7 C 0.3334(8) 0.59759(12) 0.7294(3) 0.0160(7) Uani 1 1 d . . .
C8 C 0.5269(9) 0.58836(13) 0.8500(3) 0.0210(8) Uani 1 1 d . . .
H8 H 0.5669 0.6137 0.9101 0.025 Uiso 1 1 calc R . .
C9 C 0.6607(9) 0.54192(13) 0.8817(3) 0.0211(8) Uani 1 1 d . . .
H9 H 0.7912 0.5361 0.9622 0.025 Uiso 1 1 calc R . .
C10 C 0.5990(9) 0.50471(12) 0.7936(3) 0.0213(8) Uani 1 1 d . . .
C11 C 0.4146(10) 0.51155(13) 0.6721(3) 0.0227(8) Uani 1 1 d . . .
H11 H 0.3775 0.4861 0.6125 0.027 Uiso 1 1 calc R . .
C12 C 0.2883(9) 0.55820(13) 0.6438(3) 0.0192(8) 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 C10 1.363(4) . ?
F2 C12 1.375(4) . ?
O1 C6 1.224(4) . ?
N1 C1 1.332(4) . ?
N1 C5 1.341(5) . ?
N2 C6 1.373(4) . ?
N2 C4 1.403(4) . ?
N2 H2X 0.9626 . ?
N3 C6 1.374(4) . ?
N3 C7 1.406(4) . ?
N3 H3X 0.8532 . ?
C1 C2 1.389(5) . ?
C1 H1 0.9300 . ?
C2 C3 1.374(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.397(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.398(4) . ?
C5 H5 0.9300 . ?
C7 C12 1.391(5) . ?
C7 C8 1.393(5) . ?
C8 C9 1.386(5) . ?
C8 H8 0.9300 . ?
C9 C10 1.367(5) . ?
C9 H9 0.9300 . ?
C10 C11 1.376(5) . ?
C11 C12 1.376(5) . ?
C11 H11 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
C1 N1 C5 118.6(3) . . ?
C6 N2 C4 127.3(3) . . ?
C6 N2 H2X 111.4 . . ?
C4 N2 H2X 120.8 . . ?
C6 N3 C7 125.2(3) . . ?
C6 N3 H3X 115.8 . . ?
C7 N3 H3X 117.7 . . ?
N1 C1 C2 122.5(3) . . ?
N1 C1 H1 118.8 . . ?
C2 C1 H1 118.8 . . ?
C3 C2 C1 119.1(3) . . ?
C3 C2 H2 120.4 . . ?
C1 C2 H2 120.4 . . ?
C2 C3 C4 119.3(3) . . ?
C2 C3 H3 120.3 . . ?
C4 C3 H3 120.3 . . ?
C3 C4 C5 117.7(3) . . ?
C3 C4 N2 118.6(3) . . ?
C5 C4 N2 123.8(3) . . ?
N1 C5 C4 122.8(3) . . ?
N1 C5 H5 118.6 . . ?
C4 C5 H5 118.6 . . ?
O1 C6 N2 124.0(3) . . ?
O1 C6 N3 124.1(3) . . ?
N2 C6 N3 111.9(3) . . ?
C12 C7 C8 116.5(3) . . ?
C12 C7 N3 117.6(3) . . ?
C8 C7 N3 125.9(3) . . ?
C9 C8 C7 120.8(3) . . ?
C9 C8 H8 119.6 . . ?
C7 C8 H8 119.6 . . ?
C10 C9 C8 119.4(3) . . ?
C10 C9 H9 120.3 . . ?
C8 C9 H9 120.3 . . ?
F1 C10 C9 119.4(3) . . ?
F1 C10 C11 118.0(3) . . ?
C9 C10 C11 122.6(3) . . ?
C12 C11 C10 116.3(3) . . ?
C12 C11 H11 121.9 . . ?
C10 C11 H11 121.9 . . ?
F2 C12 C11 118.1(3) . . ?
F2 C12 C7 117.5(3) . . ?
C11 C12 C7 124.3(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
C5 N1 C1 C2 -0.2(5) . . . . ?
N1 C1 C2 C3 0.3(5) . . . . ?
C1 C2 C3 C4 0.6(5) . . . . ?
C2 C3 C4 C5 -1.5(5) . . . . ?
C2 C3 C4 N2 179.3(3) . . . . ?
C6 N2 C4 C3 175.3(3) . . . . ?
C6 N2 C4 C5 -3.7(5) . . . . ?
C1 N1 C5 C4 -0.8(5) . . . . ?
C3 C4 C5 N1 1.7(5) . . . . ?
N2 C4 C5 N1 -179.2(3) . . . . ?
C4 N2 C6 O1 3.2(6) . . . . ?
C4 N2 C6 N3 -176.3(3) . . . . ?
C7 N3 C6 O1 9.1(5) . . . . ?
C7 N3 C6 N2 -171.4(3) . . . . ?
C6 N3 C7 C12 162.7(3) . . . . ?
C6 N3 C7 C8 -16.7(5) . . . . ?
C12 C7 C8 C9 -0.9(5) . . . . ?
N3 C7 C8 C9 178.5(3) . . . . ?
C7 C8 C9 C10 -0.5(5) . . . . ?
C8 C9 C10 F1 -179.7(3) . . . . ?
C8 C9 C10 C11 1.5(6) . . . . ?
F1 C10 C11 C12 -179.8(3) . . . . ?
C9 C10 C11 C12 -1.0(5) . . . . ?
C10 C11 C12 F2 -179.5(3) . . . . ?
C10 C11 C12 C7 -0.5(5) . . . . ?
C8 C7 C12 F2 -179.5(3) . . . . ?
N3 C7 C12 F2 1.0(4) . . . . ?
C8 C7 C12 C11 1.4(5) . . . . ?
N3 C7 C12 C11 -178.0(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H2X N1 0.96 2.13 3.047(4) 157.8 4_575
N3 H3X N1 0.85 2.28 3.086(4) 158.5 4_575

_diffrn_measured_fraction_theta_max 0.968
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.968
_refine_diff_density_max         1.110
_refine_diff_density_min         -1.124
_refine_diff_density_rms         0.325
_database_code_depnum_ccdc_archive 'CCDC 1002411'
#######################################################################
#
#                 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_kp7

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H10 N4 O3'
_chemical_formula_weight         258.24

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'
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           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                   11.9799(18)
_cell_length_b                   7.3695(13)
_cell_length_c                   25.427(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2244.9(6)
_cell_formula_units_Z            8
_cell_measurement_temperature    107(2)
_cell_measurement_reflns_used    2811
_cell_measurement_theta_min      7.268
_cell_measurement_theta_max      65.367

_exptl_crystal_description       Rod
_exptl_crystal_colour            Yellow
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.528
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1072
_exptl_absorpt_coefficient_mu    0.958
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.6030
_exptl_absorpt_correction_T_max  0.7527
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      107(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 APEX DUO'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6614
_diffrn_reflns_av_R_equivalents  0.0445
_diffrn_reflns_av_sigmaI/netI    0.0454
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         7.27
_diffrn_reflns_theta_max         64.99
_reflns_number_total             1819
_reflns_number_gt                1602
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0463P)²+0.6252P] 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         1819
_refine_ls_number_parameters     180
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0407
_refine_ls_R_factor_gt           0.0354
_refine_ls_wR_factor_ref         0.0921
_refine_ls_wR_factor_gt          0.0875
_refine_ls_goodness_of_fit_ref   1.092
_refine_ls_restrained_S_all      1.092
_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
O1 O 0.83864(8) -0.02895(15) 0.36476(4) 0.0210(3) Uani 1 1 d . . .
O2 O 0.44944(9) 0.16829(18) 0.36272(5) 0.0302(3) Uani 1 1 d . . .
O3 O 0.42318(10) 0.39835(17) 0.41412(5) 0.0323(3) Uani 1 1 d . . .
N1 N 0.98303(10) -0.18406(18) 0.22083(5) 0.0206(3) Uani 1 1 d . . .
N2 N 0.72258(10) -0.11393(18) 0.29710(5) 0.0183(3) Uani 1 1 d . . .
H2X H 0.6517(19) -0.130(3) 0.2875(9) 0.038(6) Uiso 1 1 d . . .
N3 N 0.64820(11) 0.01159(18) 0.37084(5) 0.0191(3) Uani 1 1 d . . .
H3X H 0.5926(19) 0.022(3) 0.3498(9) 0.037(6) Uiso 1 1 d . . .
N4 N 0.47022(10) 0.25557(18) 0.40298(5) 0.0219(3) Uani 1 1 d . . .
C1 C 0.94033(12) -0.2693(2) 0.17903(6) 0.0205(4) Uani 1 1 d . . .
H1 H 0.9893 -0.3068 0.1517 0.025 Uiso 1 1 calc R . .
C2 C 0.82708(12) -0.3052(2) 0.17403(6) 0.0208(4) Uani 1 1 d . . .
H2 H 0.7990 -0.3657 0.1438 0.025 Uiso 1 1 calc R . .
C3 C 0.75634(12) -0.2513(2) 0.21371(6) 0.0192(4) Uani 1 1 d . . .
H3 H 0.6783 -0.2720 0.2107 0.023 Uiso 1 1 calc R . .
C4 C 0.79947(12) -0.1664(2) 0.25826(6) 0.0162(3) Uani 1 1 d . . .
C5 C 0.91440(12) -0.1350(2) 0.26015(6) 0.0186(3) Uani 1 1 d . . .
H5 H 0.9451 -0.0770 0.2902 0.022 Uiso 1 1 calc R . .
C6 C 0.74567(12) -0.0436(2) 0.34559(6) 0.0170(3) Uani 1 1 d . . .
C7 C 0.63886(12) 0.0679(2) 0.42266(6) 0.0168(3) Uani 1 1 d . . .
C8 C 0.71388(12) 0.0097(2) 0.46178(6) 0.0202(4) Uani 1 1 d . . .
H8 H 0.7748 -0.0661 0.4523 0.024 Uiso 1 1 calc R . .
C9 C 0.70078(13) 0.0605(2) 0.51353(6) 0.0218(4) Uani 1 1 d . . .
H9 H 0.7522 0.0173 0.5391 0.026 Uiso 1 1 calc R . .
C10 C 0.61382(13) 0.1739(2) 0.52930(6) 0.0222(4) Uani 1 1 d . . .
H10 H 0.6056 0.2072 0.5652 0.027 Uiso 1 1 calc R . .
C11 C 0.54008(12) 0.2366(2) 0.49196(6) 0.0202(4) Uani 1 1 d . . .
H11 H 0.4809 0.3155 0.5018 0.024 Uiso 1 1 calc R . .
C12 C 0.55255(12) 0.1841(2) 0.43969(6) 0.0178(3) 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
O1 C6 1.2206(18) . ?
O2 N4 1.2344(18) . ?
O3 N4 1.2267(18) . ?
N1 C1 1.336(2) . ?
N1 C5 1.344(2) . ?
N2 C6 1.366(2) . ?
N2 C4 1.4047(19) . ?
N2 H2X 0.89(2) . ?
N3 C7 1.386(2) . ?
N3 C6 1.3933(19) . ?
N3 H3X 0.86(2) . ?
N4 C12 1.457(2) . ?
C1 C2 1.388(2) . ?
C1 H1 0.9500 . ?
C2 C3 1.376(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.393(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.397(2) . ?
C5 H5 0.9500 . ?
C7 C8 1.407(2) . ?
C7 C12 1.410(2) . ?
C8 C9 1.377(2) . ?
C8 H8 0.9500 . ?
C9 C10 1.394(2) . ?
C9 H9 0.9500 . ?
C10 C11 1.377(2) . ?
C10 H10 0.9500 . ?
C11 C12 1.392(2) . ?
C11 H11 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C5 118.95(13) . . ?
C6 N2 C4 127.32(12) . . ?
C6 N2 H2X 119.4(14) . . ?
C4 N2 H2X 113.2(14) . . ?
C7 N3 C6 126.38(13) . . ?
C7 N3 H3X 120.2(14) . . ?
C6 N3 H3X 112.9(15) . . ?
O3 N4 O2 123.07(13) . . ?
O3 N4 C12 118.27(14) . . ?
O2 N4 C12 118.65(13) . . ?
N1 C1 C2 122.44(14) . . ?
N1 C1 H1 118.8 . . ?
C2 C1 H1 118.8 . . ?
C3 C2 C1 118.67(14) . . ?
C3 C2 H2 120.7 . . ?
C1 C2 H2 120.7 . . ?
C2 C3 C4 119.82(13) . . ?
C2 C3 H3 120.1 . . ?
C4 C3 H3 120.1 . . ?
C3 C4 C5 117.89(13) . . ?
C3 C4 N2 116.87(13) . . ?
C5 C4 N2 125.21(14) . . ?
N1 C5 C4 122.19(14) . . ?
N1 C5 H5 118.9 . . ?
C4 C5 H5 118.9 . . ?
O1 C6 N2 125.38(13) . . ?
O1 C6 N3 123.70(14) . . ?
N2 C6 N3 110.92(12) . . ?
N3 C7 C8 121.94(13) . . ?
N3 C7 C12 122.19(13) . . ?
C8 C7 C12 115.86(13) . . ?
C9 C8 C7 121.31(14) . . ?
C9 C8 H8 119.3 . . ?
C7 C8 H8 119.3 . . ?
C8 C9 C10 121.52(14) . . ?
C8 C9 H9 119.2 . . ?
C10 C9 H9 119.2 . . ?
C11 C10 C9 118.85(14) . . ?
C11 C10 H10 120.6 . . ?
C9 C10 H10 120.6 . . ?
C10 C11 C12 119.73(14) . . ?
C10 C11 H11 120.1 . . ?
C12 C11 H11 120.1 . . ?
C11 C12 C7 122.72(14) . . ?
C11 C12 N4 116.00(13) . . ?
C7 C12 N4 121.28(13) . . ?

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
C5 N1 C1 C2 1.7(2) . . . . ?
N1 C1 C2 C3 -0.2(2) . . . . ?
C1 C2 C3 C4 -1.4(2) . . . . ?
C2 C3 C4 C5 1.6(2) . . . . ?
C2 C3 C4 N2 179.63(14) . . . . ?
C6 N2 C4 C3 173.88(14) . . . . ?
C6 N2 C4 C5 -8.2(2) . . . . ?
C1 N1 C5 C4 -1.5(2) . . . . ?
C3 C4 C5 N1 -0.1(2) . . . . ?
N2 C4 C5 N1 -177.98(14) . . . . ?
C4 N2 C6 O1 -6.5(2) . . . . ?
C4 N2 C6 N3 173.07(14) . . . . ?
C7 N3 C6 O1 -8.9(2) . . . . ?
C7 N3 C6 N2 171.51(14) . . . . ?
C6 N3 C7 C8 -26.3(2) . . . . ?
C6 N3 C7 C12 154.93(15) . . . . ?
N3 C7 C8 C9 -177.16(14) . . . . ?
C12 C7 C8 C9 1.7(2) . . . . ?
C7 C8 C9 C10 -1.0(2) . . . . ?
C8 C9 C10 C11 -0.3(2) . . . . ?
C9 C10 C11 C12 0.9(2) . . . . ?
C10 C11 C12 C7 -0.2(2) . . . . ?
C10 C11 C12 N4 179.46(13) . . . . ?
N3 C7 C12 C11 177.76(14) . . . . ?
C8 C7 C12 C11 -1.1(2) . . . . ?
N3 C7 C12 N4 -1.9(2) . . . . ?
C8 C7 C12 N4 179.27(13) . . . . ?
O3 N4 C12 C11 25.29(19) . . . . ?
O2 N4 C12 C11 -153.32(14) . . . . ?
O3 N4 C12 C7 -155.01(14) . . . . ?
O2 N4 C12 C7 26.4(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H2X N1 0.89(2) 2.07(2) 2.9515(18) 169(2) 6_556
N3 H3X O2 0.86(2) 2.05(2) 2.6544(17) 126.6(19) .

_diffrn_measured_fraction_theta_max 0.951
_diffrn_reflns_theta_full        64.99
_diffrn_measured_fraction_theta_full 0.950
_refine_diff_density_max         0.189
_refine_diff_density_min         -0.307
_refine_diff_density_rms         0.052
_database_code_depnum_ccdc_archive 'CCDC 1002412'
#######################################################################
#
#                 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_kp10

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            KP121
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H9 F2 N3 O, H2 O'
_chemical_formula_sum            'C12 H11 F2 N3 O2'
_chemical_formula_weight         267.24

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'
F F 0.0171 0.0103 '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'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'

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

_cell_length_a                   8.9104(3)
_cell_length_b                   9.9683(3)
_cell_length_c                   13.1855(4)
_cell_angle_alpha                91.865(2)
_cell_angle_beta                 92.788(2)
_cell_angle_gamma                91.591(2)
_cell_volume                     1168.65(6)
_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       needle
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.519
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             552
_exptl_absorpt_coefficient_mu    0.127
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.9631
_exptl_absorpt_correction_T_max  0.9940
_exptl_absorpt_process_details   'APEX 2'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(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
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            80707
_diffrn_reflns_av_R_equivalents  0.1195
_diffrn_reflns_av_sigmaI/netI    0.0581
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.55
_diffrn_reflns_theta_max         27.50
_reflns_number_total             5368
_reflns_number_gt                3447
_reflns_threshold_expression     >2sigma(I)

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

_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)+(0.0630P)²+0.3368P] 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         5368
_refine_ls_number_parameters     430
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0940
_refine_ls_R_factor_gt           0.0485
_refine_ls_wR_factor_ref         0.1276
_refine_ls_wR_factor_gt          0.1131
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_restrained_S_all      1.024
_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 0.26294(15) -0.04371(13) 0.71866(9) 0.0316(3) Uani 1 1 d . . .
F2 F 0.59708(16) -0.34679(14) 0.57940(10) 0.0379(4) Uani 1 1 d . . .
O1 O 0.14791(17) 0.08256(15) 0.37144(10) 0.0221(4) Uani 1 1 d . . .
N2 N 0.0385(2) 0.22104(19) 0.48672(15) 0.0206(4) Uani 1 1 d . . .
N3 N 0.1897(2) 0.05655(19) 0.54183(14) 0.0200(4) Uani 1 1 d . . .
N1 N -0.2015(2) 0.4894(2) 0.30639(15) 0.0319(5) Uani 1 1 d . . .
C6 C 0.1271(2) 0.1177(2) 0.45944(15) 0.0182(5) Uani 1 1 d . . .
C7 C 0.2908(2) -0.0485(2) 0.54252(15) 0.0180(5) Uani 1 1 d . . .
C3 C -0.0400(2) 0.3065(2) 0.42270(16) 0.0192(5) Uani 1 1 d . . .
C12 C 0.3583(2) -0.1045(2) 0.45821(17) 0.0211(5) Uani 1 1 d . . .
C11 C 0.4611(2) -0.2048(2) 0.47071(17) 0.0222(5) Uani 1 1 d . . .
C8 C 0.3313(2) -0.0990(2) 0.63686(15) 0.0206(5) Uani 1 1 d . . .
C2 C -0.1359(2) 0.3969(2) 0.46725(17) 0.0239(5) Uani 1 1 d . . .
C9 C 0.4332(3) -0.1974(2) 0.65166(18) 0.0248(5) Uani 1 1 d . . .
C10 C 0.4965(2) -0.2488(2) 0.56626(17) 0.0244(5) Uani 1 1 d . . .
C4 C -0.0262(3) 0.3099(2) 0.31805(18) 0.0273(5) Uani 1 1 d . . .
C1 C -0.2131(3) 0.4846(2) 0.40674(19) 0.0271(5) Uani 1 1 d . . .
C5 C -0.1093(3) 0.4013(3) 0.2650(2) 0.0336(6) Uani 1 1 d . . .
F4 F 0.91751(15) -0.20676(13) -0.07317(10) 0.0342(3) Uani 1 1 d . . .
F3 F 0.55655(15) 0.07468(14) -0.21727(9) 0.0318(3) Uani 1 1 d . . .
O2 O 0.57175(16) 0.29919(15) 0.11679(10) 0.0232(4) Uani 1 1 d . . .
N5 N 0.3776(2) 0.37449(18) 0.01557(14) 0.0195(4) Uani 1 1 d . . .
N6 N 0.5270(2) 0.21153(18) -0.04442(14) 0.0187(4) Uani 1 1 d . . .
N4 N 0.1727(2) 0.65578(18) 0.20313(14) 0.0249(4) Uani 1 1 d . . .
C19 C 0.6315(2) 0.1093(2) -0.04539(15) 0.0166(4) Uani 1 1 d . . .
C23 C 0.8187(3) -0.0341(2) 0.02743(17) 0.0225(5) Uani 1 1 d . . .
C22 C 0.8237(2) -0.1026(2) -0.06352(17) 0.0207(5) Uani 1 1 d . . .
C15 C 0.3149(2) 0.4668(2) 0.08147(15) 0.0186(5) Uani 1 1 d . . .
C24 C 0.7232(2) 0.0726(2) 0.03711(17) 0.0206(5) Uani 1 1 d . . .
C16 C 0.1939(3) 0.5382(2) 0.04396(17) 0.0227(5) Uani 1 1 d . . .
C18 C 0.4987(2) 0.2951(2) 0.03639(15) 0.0177(5) Uani 1 1 d . . .
C21 C 0.7368(2) -0.0692(2) -0.14750(17) 0.0238(5) Uani 1 1 d . . .
C20 C 0.6438(2) 0.0367(2) -0.13618(15) 0.0197(5) Uani 1 1 d . . .
C14 C 0.3648(3) 0.4934(2) 0.18202(16) 0.0236(5) Uani 1 1 d . . .
C13 C 0.2892(3) 0.5870(2) 0.23786(18) 0.0272(5) Uani 1 1 d . . .
C17 C 0.1283(3) 0.6300(2) 0.10640(18) 0.0243(5) Uani 1 1 d . . .
O3 O 0.00348(19) 0.16597(19) 0.70346(12) 0.0256(4) Uani 1 1 d . . .
O4 O 0.7206(2) 0.70512(17) 0.18962(12) 0.0308(4) Uani 1 1 d D . .
H1 H -0.275(3) 0.547(2) 0.4374(17) 0.021(6) Uiso 1 1 d . . .
H2A H -0.145(2) 0.398(2) 0.5483(18) 0.025 Uiso 1 1 d . . .
H2B H 0.023(2) 0.228(2) 0.5420(17) 0.010(6) Uiso 1 1 d . . .
H3 H 0.165(3) 0.085(3) 0.595(2) 0.033(8) Uiso 1 1 d . . .
H3A H -0.076(3) 0.235(3) 0.729(2) 0.047(8) Uiso 1 1 d . . .
H3B H -0.039(3) 0.094(3) 0.696(2) 0.044(9) Uiso 1 1 d . . .
H4 H 0.041(3) 0.253(2) 0.2884(17) 0.020(6) Uiso 1 1 d . . .
H4A H 0.739(3) 0.6273(17) 0.2219(17) 0.030(7) Uiso 1 1 d D . .
H4B H 0.786(3) 0.766(3) 0.210(2) 0.069(11) Uiso 1 1 d D . .
H5A H -0.098(3) 0.405(3) 0.195(2) 0.037(7) Uiso 1 1 d . . .
H5B H 0.336(3) 0.363(3) -0.040(2) 0.031(7) Uiso 1 1 d . . .
H6 H 0.472(3) 0.220(2) -0.0952(19) 0.026(7) Uiso 1 1 d . . .
H9 H 0.459(3) -0.231(2) 0.7191(19) 0.032(7) Uiso 1 1 d . . .
H11 H 0.510(3) -0.240(2) 0.4135(18) 0.027(6) Uiso 1 1 d . . .
H12 H 0.338(2) -0.073(2) 0.3930(17) 0.017(6) Uiso 1 1 d . . .
H13 H 0.317(3) 0.603(2) 0.3031(19) 0.024(6) Uiso 1 1 d . . .
H14 H 0.446(2) 0.452(2) 0.2103(16) 0.015(5) Uiso 1 1 d . . .
H16 H 0.158(2) 0.5210(19) -0.0277(16) 0.008(5) Uiso 1 1 d . . .
H17 H 0.052(3) 0.676(2) 0.0804(18) 0.030(7) Uiso 1 1 d . . .
H21 H 0.740(3) -0.120(2) -0.214(2) 0.037(7) Uiso 1 1 d . . .
H23 H 0.878(3) -0.053(2) 0.0822(19) 0.031(7) Uiso 1 1 d . . .
H24 H 0.722(2) 0.115(2) 0.1001(17) 0.017(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 1.372(2) . ?
F2 C10 1.354(2) . ?
O1 C6 1.225(2) . ?
N2 C6 1.365(3) . ?
N2 C3 1.396(3) . ?
N2 H2B 0.75(2) . ?
N3 C6 1.366(3) . ?
N3 C7 1.400(3) . ?
N3 H3 0.80(3) . ?
N1 C1 1.335(3) . ?
N1 C5 1.340(3) . ?
C7 C8 1.392(3) . ?
C7 C12 1.397(3) . ?
C3 C4 1.393(3) . ?
C3 C2 1.395(3) . ?
C12 C11 1.383(3) . ?
C12 H12 0.93(2) . ?
C11 C10 1.373(3) . ?
C11 H11 0.95(2) . ?
C8 C9 1.368(3) . ?
C2 C1 1.378(3) . ?
C2 H2A 1.07(2) . ?
C9 C10 1.374(3) . ?
C9 H9 0.98(3) . ?
C4 C5 1.377(3) . ?
C4 H4 0.92(2) . ?
C1 H1 0.94(2) . ?
C5 H5A 0.93(3) . ?
F4 C22 1.358(2) . ?
F3 C20 1.361(2) . ?
O2 C18 1.215(2) . ?
N5 C18 1.378(3) . ?
N5 C15 1.392(3) . ?
N5 H5B 0.81(3) . ?
N6 C18 1.368(3) . ?
N6 C19 1.400(3) . ?
N6 H6 0.82(3) . ?
N4 C13 1.331(3) . ?
N4 C17 1.332(3) . ?
C19 C20 1.389(3) . ?
C19 C24 1.393(3) . ?
C23 C22 1.364(3) . ?
C23 C24 1.387(3) . ?
C23 H23 0.90(3) . ?
C22 C21 1.375(3) . ?
C15 C16 1.388(3) . ?
C15 C14 1.392(3) . ?
C24 H24 0.92(2) . ?
C16 C17 1.372(3) . ?
C16 H16 0.99(2) . ?
C21 C20 1.368(3) . ?
C21 H21 1.00(3) . ?
C14 C13 1.380(3) . ?
C14 H14 0.91(2) . ?
C13 H13 0.89(2) . ?
C17 H17 0.89(3) . ?
O3 H3A 1.06(3) . ?
O3 H3B 0.80(3) . ?
O4 H4A 0.912(14) . ?
O4 H4B 0.860(15) . ?

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
C6 N2 C3 127.59(19) . . ?
C6 N2 H2B 116.2(16) . . ?
C3 N2 H2B 115.8(16) . . ?
C6 N3 C7 127.79(18) . . ?
C6 N3 H3 114.8(19) . . ?
C7 N3 H3 117.4(19) . . ?
C1 N1 C5 116.0(2) . . ?
O1 C6 N2 124.31(19) . . ?
O1 C6 N3 123.48(19) . . ?
N2 C6 N3 112.21(18) . . ?
C8 C7 C12 117.03(19) . . ?
C8 C7 N3 116.64(18) . . ?
C12 C7 N3 126.29(19) . . ?
C4 C3 C2 117.9(2) . . ?
C4 C3 N2 124.6(2) . . ?
C2 C3 N2 117.55(19) . . ?
C11 C12 C7 120.1(2) . . ?
C11 C12 H12 118.6(13) . . ?
C7 C12 H12 121.3(13) . . ?
C10 C11 C12 119.7(2) . . ?
C10 C11 H11 120.6(14) . . ?
C12 C11 H11 119.7(14) . . ?
C9 C8 F1 119.53(19) . . ?
C9 C8 C7 124.24(19) . . ?
F1 C8 C7 116.23(18) . . ?
C1 C2 C3 119.2(2) . . ?
C1 C2 H2A 122.0(12) . . ?
C3 C2 H2A 118.7(12) . . ?
C8 C9 C10 116.4(2) . . ?
C8 C9 H9 121.9(14) . . ?
C10 C9 H9 121.7(14) . . ?
F2 C10 C11 120.2(2) . . ?
F2 C10 C9 117.2(2) . . ?
C11 C10 C9 122.6(2) . . ?
C5 C4 C3 118.0(2) . . ?
C5 C4 H4 123.6(14) . . ?
C3 C4 H4 118.4(14) . . ?
N1 C1 C2 123.8(2) . . ?
N1 C1 H1 117.3(14) . . ?
C2 C1 H1 118.8(14) . . ?
N1 C5 C4 125.1(2) . . ?
N1 C5 H5A 117.0(16) . . ?
C4 C5 H5A 117.9(16) . . ?
C18 N5 C15 127.10(19) . . ?
C18 N5 H5B 116.0(18) . . ?
C15 N5 H5B 116.8(18) . . ?
C18 N6 C19 126.45(18) . . ?
C18 N6 H6 115.3(17) . . ?
C19 N6 H6 118.1(17) . . ?
C13 N4 C17 115.72(19) . . ?
C20 C19 C24 116.96(19) . . ?
C20 C19 N6 117.28(18) . . ?
C24 C19 N6 125.76(18) . . ?
C22 C23 C24 119.8(2) . . ?
C22 C23 H23 122.7(15) . . ?
C24 C23 H23 117.5(15) . . ?
F4 C22 C23 119.8(2) . . ?
F4 C22 C21 118.05(19) . . ?
C23 C22 C21 122.1(2) . . ?
C16 C15 N5 117.53(19) . . ?
C16 C15 C14 117.5(2) . . ?
N5 C15 C14 124.9(2) . . ?
C23 C24 C19 120.3(2) . . ?
C23 C24 H24 116.6(13) . . ?
C19 C24 H24 123.1(13) . . ?
C17 C16 C15 119.5(2) . . ?
C17 C16 H16 122.0(11) . . ?
C15 C16 H16 118.5(11) . . ?
O2 C18 N6 124.20(19) . . ?
O2 C18 N5 123.97(19) . . ?
N6 C18 N5 111.84(18) . . ?
C20 C21 C22 117.0(2) . . ?
C20 C21 H21 120.9(15) . . ?
C22 C21 H21 122.1(15) . . ?
F3 C20 C21 119.35(18) . . ?
F3 C20 C19 116.84(18) . . ?
C21 C20 C19 123.8(2) . . ?
C13 C14 C15 117.9(2) . . ?
C13 C14 H14 120.5(13) . . ?
C15 C14 H14 121.6(13) . . ?
N4 C13 C14 125.3(2) . . ?
N4 C13 H13 115.3(15) . . ?
C14 C13 H13 119.4(15) . . ?
N4 C17 C16 124.1(2) . . ?
N4 C17 H17 117.9(15) . . ?
C16 C17 H17 118.0(15) . . ?
H3A O3 H3B 107(3) . . ?
H4A O4 H4B 110(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
C3 N2 C6 O1 -1.8(4) . . . . ?
C3 N2 C6 N3 178.7(2) . . . . ?
C7 N3 C6 O1 3.4(4) . . . . ?
C7 N3 C6 N2 -177.13(19) . . . . ?
C6 N3 C7 C8 -176.2(2) . . . . ?
C6 N3 C7 C12 6.0(4) . . . . ?
C6 N2 C3 C4 -8.0(4) . . . . ?
C6 N2 C3 C2 173.7(2) . . . . ?
C8 C7 C12 C11 -0.4(3) . . . . ?
N3 C7 C12 C11 177.4(2) . . . . ?
C7 C12 C11 C10 -0.1(3) . . . . ?
C12 C7 C8 C9 0.9(3) . . . . ?
N3 C7 C8 C9 -177.2(2) . . . . ?
C12 C7 C8 F1 -179.44(18) . . . . ?
N3 C7 C8 F1 2.5(3) . . . . ?
C4 C3 C2 C1 0.3(3) . . . . ?
N2 C3 C2 C1 178.8(2) . . . . ?
F1 C8 C9 C10 179.60(19) . . . . ?
C7 C8 C9 C10 -0.7(3) . . . . ?
C12 C11 C10 F2 -179.9(2) . . . . ?
C12 C11 C10 C9 0.3(4) . . . . ?
C8 C9 C10 F2 -179.7(2) . . . . ?
C8 C9 C10 C11 0.1(3) . . . . ?
C2 C3 C4 C5 -0.6(3) . . . . ?
N2 C3 C4 C5 -178.9(2) . . . . ?
C5 N1 C1 C2 0.7(4) . . . . ?
C3 C2 C1 N1 -0.4(4) . . . . ?
C1 N1 C5 C4 -1.0(4) . . . . ?
C3 C4 C5 N1 1.0(4) . . . . ?
C18 N6 C19 C20 -179.28(19) . . . . ?
C18 N6 C19 C24 1.5(3) . . . . ?
C24 C23 C22 F4 179.72(19) . . . . ?
C24 C23 C22 C21 0.2(3) . . . . ?
C18 N5 C15 C16 179.0(2) . . . . ?
C18 N5 C15 C14 -0.7(3) . . . . ?
C22 C23 C24 C19 0.6(3) . . . . ?
C20 C19 C24 C23 -1.6(3) . . . . ?
N6 C19 C24 C23 177.6(2) . . . . ?
N5 C15 C16 C17 179.8(2) . . . . ?
C14 C15 C16 C17 -0.4(3) . . . . ?
C19 N6 C18 O2 7.0(3) . . . . ?
C19 N6 C18 N5 -173.17(19) . . . . ?
C15 N5 C18 O2 -2.7(3) . . . . ?
C15 N5 C18 N6 177.47(19) . . . . ?
F4 C22 C21 C20 -179.55(18) . . . . ?
C23 C22 C21 C20 0.0(3) . . . . ?
C22 C21 C20 F3 179.35(19) . . . . ?
C22 C21 C20 C19 -1.0(3) . . . . ?
C24 C19 C20 F3 -178.55(19) . . . . ?
N6 C19 C20 F3 2.2(3) . . . . ?
C24 C19 C20 C21 1.8(3) . . . . ?
N6 C19 C20 C21 -177.4(2) . . . . ?
C16 C15 C14 C13 1.0(3) . . . . ?
N5 C15 C14 C13 -179.3(2) . . . . ?
C17 N4 C13 C14 -0.1(3) . . . . ?
C15 C14 C13 N4 -0.8(4) . . . . ?
C13 N4 C17 C16 0.7(3) . . . . ?
C15 C16 C17 N4 -0.5(4) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H2B O3 0.75(2) 2.25(2) 2.957(2) 158(2) .
N3 H3 O3 0.80(3) 2.22(3) 2.963(2) 155(2) .
N5 H5B O4 0.81(3) 2.10(3) 2.882(2) 163(2) 2_665
O4 H4A N1 0.912(14) 1.869(15) 2.769(3) 169(2) 1_655
O4 H4B O3 0.860(15) 2.22(2) 3.009(2) 152(3) 2_666
O3 H3A N4 1.06(3) 1.67(3) 2.709(2) 166(2) 2_566
O3 H3B O1 0.80(3) 2.13(3) 2.908(2) 163(3) 2_556
N6 H6 O4 0.82(3) 2.23(3) 3.003(3) 157(2) 2_665

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        27.50
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.547
_refine_diff_density_min         -0.337
_refine_diff_density_rms         0.054
_database_code_depnum_ccdc_archive 'CCDC 1002413'
#######################################################################
#
#                 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_kp11

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H14 N4 O4'
_chemical_formula_weight         290.28

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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                   8.1756(16)
_cell_length_b                   14.365(3)
_cell_length_c                   11.375(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 92.01(3)
_cell_angle_gamma                90.00
_cell_volume                     1335.1(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    162(2)
_cell_measurement_reflns_used    5271
_cell_measurement_theta_min      2.2846
_cell_measurement_theta_max      31.3458

_exptl_crystal_description       Block
_exptl_crystal_colour            Yellow
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.31
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.444
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             608
_exptl_absorpt_coefficient_mu    0.110
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.8995
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   CrystalClear

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      162(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  'Rigaku saturn 724'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10627
_diffrn_reflns_av_R_equivalents  0.0172
_diffrn_reflns_av_sigmaI/netI    0.0113
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.49
_diffrn_reflns_theta_max         24.99
_reflns_number_total             2328
_reflns_number_gt                2289
_reflns_threshold_expression     >2sigma(I)

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

_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)+(0.0493P)²+0.4232P] 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         2328
_refine_ls_number_parameters     203
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0358
_refine_ls_R_factor_gt           0.0353
_refine_ls_wR_factor_ref         0.0921
_refine_ls_wR_factor_gt          0.0918
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_restrained_S_all      1.063
_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
O1 O 0.35727(10) 0.08165(6) 0.41867(7) 0.0300(2) Uani 1 1 d . . .
O2 O 0.40952(16) 0.51219(7) 0.39040(10) 0.0534(3) Uani 1 1 d . . .
O3 O 0.25863(14) 0.41123(7) 0.47472(10) 0.0480(3) Uani 1 1 d . . .
N1 N 0.06136(14) -0.09886(8) 0.75298(9) 0.0357(3) Uani 1 1 d . . .
N2 N 0.15147(12) 0.13078(7) 0.53659(9) 0.0257(2) Uani 1 1 d . . .
H2X H 0.0799(19) 0.1784(11) 0.5485(13) 0.037(4) Uiso 1 1 d . . .
N3 N 0.26615(13) 0.23358(7) 0.41196(9) 0.0275(3) Uani 1 1 d . . .
H3X H 0.2207(19) 0.2724(12) 0.4542(14) 0.035(4) Uiso 1 1 d . . .
N4 N 0.35744(14) 0.43257(8) 0.39970(10) 0.0361(3) Uani 1 1 d . . .
C1 C 0.18688(17) -0.09909(9) 0.68036(11) 0.0331(3) Uani 1 1 d . . .
H1 H 0.2545 -0.1529 0.6803 0.040 Uiso 1 1 calc R . .
C2 C 0.22550(15) -0.02735(8) 0.60570(10) 0.0274(3) Uani 1 1 d . . .
H2 H 0.3166 -0.0318 0.5564 0.033 Uiso 1 1 calc R . .
C3 C 0.12706(14) 0.05203(8) 0.60467(10) 0.0240(3) Uani 1 1 d . . .
C4 C -0.00448(15) 0.05337(9) 0.67990(11) 0.0303(3) Uani 1 1 d . . .
H4 H -0.0747 0.1060 0.6819 0.036 Uiso 1 1 calc R . .
C5 C -0.03151(16) -0.02218(10) 0.75102(11) 0.0348(3) Uani 1 1 d . . .
H5 H -0.1214 -0.0197 0.8017 0.042 Uiso 1 1 calc R . .
C6 C 0.26649(14) 0.14219(8) 0.45254(10) 0.0236(3) Uani 1 1 d . . .
C7 C 0.36548(14) 0.26742(9) 0.32471(11) 0.0266(3) Uani 1 1 d . . .
C8 C 0.42037(16) 0.20819(9) 0.23630(11) 0.0320(3) Uani 1 1 d . . .
H8 H 0.3863 0.1450 0.2352 0.038 Uiso 1 1 calc R . .
C9 C 0.52236(17) 0.23960(10) 0.15123(12) 0.0369(3) Uani 1 1 d . . .
H9 H 0.5587 0.1975 0.0933 0.044 Uiso 1 1 calc R . .
C10 C 0.57302(16) 0.33161(11) 0.14867(13) 0.0400(4) Uani 1 1 d . . .
H10 H 0.6456 0.3523 0.0907 0.048 Uiso 1 1 calc R . .
C11 C 0.51682(16) 0.39258(10) 0.23109(13) 0.0376(3) Uani 1 1 d . . .
H11 H 0.5482 0.4562 0.2287 0.045 Uiso 1 1 calc R . .
C12 C 0.41411(15) 0.36166(9) 0.31819(11) 0.0298(3) Uani 1 1 d . . .
O100 O -0.04701(13) 0.28512(7) 0.55927(9) 0.0404(3) Uani 1 1 d . . .
H10X H -0.050(3) 0.3190(16) 0.621(2) 0.077(7) Uiso 1 1 d . . .
C100 C -0.1244(2) 0.33322(11) 0.46486(13) 0.0444(4) Uani 1 1 d . . .
H10D H -0.1218 0.4002 0.4809 0.067 Uiso 1 1 calc R . .
H10C H -0.2384 0.3125 0.4556 0.067 Uiso 1 1 calc R . .
H10B H -0.0670 0.3204 0.3924 0.067 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
O1 C6 1.2148(15) . ?
O2 N4 1.2262(15) . ?
O3 N4 1.2341(16) . ?
N1 C5 1.3375(19) . ?
N1 C1 1.3397(18) . ?
N2 C6 1.3741(16) . ?
N2 C3 1.3893(16) . ?
N2 H2X 0.913(17) . ?
N3 C6 1.3915(16) . ?
N3 C7 1.3919(16) . ?
N3 H3X 0.832(17) . ?
N4 C12 1.4635(18) . ?
C1 C2 1.3791(18) . ?
C1 H1 0.9500 . ?
C2 C3 1.3955(17) . ?
C2 H2 0.9500 . ?
C3 C4 1.3977(18) . ?
C4 C5 1.3760(19) . ?
C4 H4 0.9500 . ?
C5 H5 0.9500 . ?
C7 C8 1.4029(18) . ?
C7 C12 1.4136(18) . ?
C8 C9 1.3754(19) . ?
C8 H8 0.9500 . ?
C9 C10 1.386(2) . ?
C9 H9 0.9500 . ?
C10 C11 1.374(2) . ?
C10 H10 0.9500 . ?
C11 C12 1.3937(19) . ?
C11 H11 0.9500 . ?
O100 C100 1.4085(18) . ?
O100 H10X 0.86(2) . ?
C100 H10D 0.9800 . ?
C100 H10C 0.9800 . ?
C100 H10B 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
C5 N1 C1 116.00(11) . . ?
C6 N2 C3 126.88(10) . . ?
C6 N2 H2X 118.1(10) . . ?
C3 N2 H2X 115.0(10) . . ?
C6 N3 C7 124.86(11) . . ?
C6 N3 H3X 115.8(11) . . ?
C7 N3 H3X 117.5(11) . . ?
O2 N4 O3 121.93(13) . . ?
O2 N4 C12 118.42(12) . . ?
O3 N4 C12 119.65(11) . . ?
N1 C1 C2 125.08(12) . . ?
N1 C1 H1 117.5 . . ?
C2 C1 H1 117.5 . . ?
C1 C2 C3 118.12(12) . . ?
C1 C2 H2 120.9 . . ?
C3 C2 H2 120.9 . . ?
N2 C3 C2 125.16(11) . . ?
N2 C3 C4 117.31(11) . . ?
C2 C3 C4 117.51(11) . . ?
C5 C4 C3 119.47(12) . . ?
C5 C4 H4 120.3 . . ?
C3 C4 H4 120.3 . . ?
N1 C5 C4 123.82(12) . . ?
N1 C5 H5 118.1 . . ?
C4 C5 H5 118.1 . . ?
O1 C6 N2 125.16(11) . . ?
O1 C6 N3 124.36(11) . . ?
N2 C6 N3 110.48(10) . . ?
N3 C7 C8 120.58(11) . . ?
N3 C7 C12 122.95(12) . . ?
C8 C7 C12 116.46(11) . . ?
C9 C8 C7 121.50(13) . . ?
C9 C8 H8 119.2 . . ?
C7 C8 H8 119.2 . . ?
C8 C9 C10 121.10(14) . . ?
C8 C9 H9 119.4 . . ?
C10 C9 H9 119.4 . . ?
C11 C10 C9 119.10(13) . . ?
C11 C10 H10 120.4 . . ?
C9 C10 H10 120.4 . . ?
C10 C11 C12 120.42(13) . . ?
C10 C11 H11 119.8 . . ?
C12 C11 H11 119.8 . . ?
C11 C12 C7 121.33(13) . . ?
C11 C12 N4 116.14(12) . . ?
C7 C12 N4 122.51(11) . . ?
C100 O100 H10X 108.8(15) . . ?
O100 C100 H10D 109.5 . . ?
O100 C100 H10C 109.5 . . ?
H10D C100 H10C 109.5 . . ?
O100 C100 H10B 109.5 . . ?
H10D C100 H10B 109.5 . . ?
H10C C100 H10B 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
C5 N1 C1 C2 -0.01(19) . . . . ?
N1 C1 C2 C3 -0.11(19) . . . . ?
C6 N2 C3 C2 5.52(19) . . . . ?
C6 N2 C3 C4 -175.95(11) . . . . ?
C1 C2 C3 N2 178.61(11) . . . . ?
C1 C2 C3 C4 0.08(16) . . . . ?
N2 C3 C4 C5 -178.57(11) . . . . ?
C2 C3 C4 C5 0.07(17) . . . . ?
C1 N1 C5 C4 0.18(19) . . . . ?
C3 C4 C5 N1 -0.2(2) . . . . ?
C3 N2 C6 O1 5.91(19) . . . . ?
C3 N2 C6 N3 -173.46(11) . . . . ?
C7 N3 C6 O1 2.19(19) . . . . ?
C7 N3 C6 N2 -178.44(11) . . . . ?
C6 N3 C7 C8 28.30(18) . . . . ?
C6 N3 C7 C12 -152.85(12) . . . . ?
N3 C7 C8 C9 -178.13(12) . . . . ?
C12 C7 C8 C9 2.95(18) . . . . ?
C7 C8 C9 C10 -0.9(2) . . . . ?
C8 C9 C10 C11 -1.6(2) . . . . ?
C9 C10 C11 C12 1.9(2) . . . . ?
C10 C11 C12 C7 0.25(19) . . . . ?
C10 C11 C12 N4 -178.36(12) . . . . ?
N3 C7 C12 C11 178.49(11) . . . . ?
C8 C7 C12 C11 -2.61(18) . . . . ?
N3 C7 C12 N4 -2.99(18) . . . . ?
C8 C7 C12 N4 175.91(11) . . . . ?
O2 N4 C12 C11 -3.70(17) . . . . ?
O3 N4 C12 C11 175.78(12) . . . . ?
O2 N4 C12 C7 177.71(12) . . . . ?
O3 N4 C12 C7 -2.81(18) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H2X O100 0.913(17) 1.857(17) 2.7648(15) 171.9(14) .
N3 H3X O3 0.832(17) 2.031(17) 2.6511(15) 130.9(14) .
N3 H3X O100 0.832(17) 2.537(16) 3.1955(17) 137.0(14) .
O100 H10X N1 0.86(2) 1.86(2) 2.7148(15) 175(2) 2_556

_diffrn_measured_fraction_theta_max 0.992
_diffrn_reflns_theta_full        24.99
_diffrn_measured_fraction_theta_full 0.992
_refine_diff_density_max         0.231
_refine_diff_density_min         -0.181
_refine_diff_density_rms         0.034
_database_code_depnum_ccdc_archive 'CCDC 1002414'
#######################################################################
#
#                 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_kp12

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H10 F3 N3 O'
_chemical_formula_sum            'C13 H10 F3 N3 O'
_chemical_formula_weight         281.24

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 0.0000 '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 0.0171 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'

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

_cell_length_a                   14.5029(12)
_cell_length_b                   12.7130(11)
_cell_length_c                   14.3436(12)
_cell_angle_alpha                90.00
_cell_angle_beta                 116.799(2)
_cell_angle_gamma                90.00
_cell_volume                     2360.6(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       octahedral
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.583
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1152
_exptl_absorpt_coefficient_mu    0.136
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  0.9616
_exptl_absorpt_correction_T_max  0.9733
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            50210
_diffrn_reflns_av_R_equivalents  0.0587
_diffrn_reflns_av_sigmaI/netI    0.0373
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.57
_diffrn_reflns_theta_max         27.50
_reflns_number_total             5363
_reflns_number_gt                2375
_reflns_threshold_expression     >2sigma(I)

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

_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)+(0.0182P)²+10.7756P] 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         5363
_refine_ls_number_parameters     401
_refine_ls_number_restraints     30
_refine_ls_R_factor_all          0.1402
_refine_ls_R_factor_gt           0.0738
_refine_ls_wR_factor_ref         0.2098
_refine_ls_wR_factor_gt          0.1897
_refine_ls_goodness_of_fit_ref   1.249
_refine_ls_restrained_S_all      1.249
_refine_ls_shift/su_max          0.262
_refine_ls_shift/su_mean         0.038

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
O1 O 0.1273(3) 0.9932(3) 0.0421(3) 0.0239(10) Uani 1 1 d . . .
N1 N -0.0148(4) 1.1861(4) -0.3167(4) 0.0233(11) Uani 1 1 d . . .
N2 N 0.0379(4) 0.9219(3) -0.1219(4) 0.0190(11) Uani 1 1 d . . .
H2A H 0.0129 0.8624 -0.1552 0.023 Uiso 1 1 calc R . .
N3 N 0.0924(4) 0.8165(3) 0.0208(4) 0.0195(11) Uani 1 1 d . . .
H3 H 0.0555 0.7696 -0.0264 0.023 Uiso 1 1 calc R . .
C1 C -0.0693(5) 1.0962(4) -0.3492(5) 0.0248(14) Uani 1 1 d . . .
H1 H -0.1218 1.0930 -0.4193 0.030 Uiso 1 1 calc R . .
C2 C -0.0535(5) 1.0085(4) -0.2871(5) 0.0232(14) Uani 1 1 d . . .
H2B H -0.0932 0.9466 -0.3150 0.028 Uiso 1 1 calc R . .
C3 C 0.0213(5) 1.0117(4) -0.1831(5) 0.0178(12) Uani 1 1 d . . .
C4 C 0.0782(5) 1.1049(4) -0.1475(5) 0.0240(14) Uani 1 1 d . . .
H4 H 0.1299 1.1117 -0.0773 0.029 Uiso 1 1 calc R . .
C5 C 0.0567(5) 1.1860(4) -0.2172(5) 0.0253(14) Uani 1 1 d . . .
H5 H 0.0967 1.2482 -0.1922 0.030 Uiso 1 1 calc R . .
C6 C 0.0896(5) 0.9171(4) -0.0143(5) 0.0174(12) Uani 1 1 d U . .
C7 C 0.1471(4) 0.7797(4) 0.1233(4) 0.0172(12) Uani 1 1 d . . .
C8 C 0.1354(4) 0.6730(3) 0.1399(5) 0.0164(12) Uani 1 1 d U . .
H8 H 0.0916 0.6300 0.0829 0.020 Uiso 1 1 calc R . .
C9 C 0.1869(5) 0.6299(5) 0.2383(5) 0.0228(13) Uani 1 1 d . . .
H9 H 0.1772 0.5578 0.2490 0.027 Uiso 1 1 calc R . .
C10 C 0.2526(5) 0.6910(4) 0.3212(5) 0.0178(12) Uani 1 1 d . . .
C11 C 0.2650(5) 0.7969(4) 0.3057(5) 0.0198(13) Uani 1 1 d . . .
H11 H 0.3100 0.8394 0.3625 0.024 Uiso 1 1 calc R . .
C12 C 0.2117(5) 0.8399(4) 0.2078(5) 0.0197(13) Uani 1 1 d . . .
H12 H 0.2195 0.9127 0.1980 0.024 Uiso 1 1 calc R . .
C13 C 0.3111(5) 0.6438(5) 0.4273(4) 0.0332(17) Uani 1 1 d . . .
F11 F 0.2854(16) 0.5481(13) 0.4347(16) 0.058(5) Uani 0.52(3) 1 d PU . .
F12 F 0.4079(6) 0.6605(18) 0.4702(10) 0.056(6) Uani 0.52(3) 1 d P . .
F13 F 0.2811(9) 0.6983(9) 0.4948(9) 0.035(3) Uani 0.52(3) 1 d P . .
F21 F 0.4044(7) 0.5923(18) 0.4333(12) 0.050(5) Uani 0.48(3) 1 d P . .
F22 F 0.348(3) 0.7008(8) 0.5061(8) 0.096(14) Uani 0.48(3) 1 d P . .
F23 F 0.2718(12) 0.5572(16) 0.4446(17) 0.052(6) Uani 0.48(3) 1 d PU . .
O2 O 0.3733(3) 0.0067(3) 0.4579(3) 0.0241(10) Uani 1 1 d . . .
N4 N 0.5145(4) -0.1861(4) 0.8174(4) 0.0232(11) Uani 1 1 d . . .
N5 N 0.4615(4) 0.0781(3) 0.6219(4) 0.0186(11) Uani 1 1 d . . .
H5A H 0.4859 0.1378 0.6548 0.022 Uiso 1 1 calc R . .
N6 N 0.4073(4) 0.1840(4) 0.4799(4) 0.0226(12) Uani 1 1 d . . .
H6 H 0.4435 0.2309 0.5275 0.027 Uiso 1 1 calc R . .
C21 C 0.2860(4) 0.1574(4) 0.2928(5) 0.0199(13) Uani 1 1 d . . .
H21 H 0.2770 0.0850 0.3030 0.024 Uiso 1 1 calc R . .
C14 C 0.4432(5) -0.1877(4) 0.7173(5) 0.0247(14) Uani 1 1 d . . .
H14 H 0.4039 -0.2502 0.6918 0.030 Uiso 1 1 calc R . .
C15 C 0.4224(5) -0.1040(4) 0.6477(5) 0.0205(13) Uani 1 1 d . . .
H15 H 0.3710 -0.1102 0.5774 0.025 Uiso 1 1 calc R . .
C16 C 0.4784(5) -0.0114(4) 0.6833(5) 0.0186(12) Uani 1 1 d . . .
C17 C 0.5531(5) -0.0092(4) 0.7875(5) 0.0215(13) Uani 1 1 d . . .
H17 H 0.5932 0.0524 0.8154 0.026 Uiso 1 1 calc R . .
C18 C 0.5685(5) -0.0962(4) 0.8496(5) 0.0240(14) Uani 1 1 d . . .
H18 H 0.6207 -0.0926 0.9198 0.029 Uiso 1 1 calc R . .
C19 C 0.4101(5) 0.0819(4) 0.5143(5) 0.0186(13) Uani 1 1 d . . .
C20 C 0.3531(5) 0.2207(4) 0.3773(5) 0.0195(13) Uani 1 1 d . A .
C22 C 0.2335(5) 0.2031(5) 0.1945(5) 0.0234(13) Uani 1 1 d . A .
H22 H 0.1885 0.1612 0.1372 0.028 Uiso 1 1 calc R . .
C23 C 0.2457(5) 0.3094(5) 0.1786(5) 0.0230(13) Uani 1 1 d . . .
C24 C 0.3122(5) 0.3711(4) 0.2619(5) 0.0172(13) Uani 1 1 d . A .
H24 H 0.3210 0.4434 0.2514 0.021 Uiso 1 1 calc R . .
C25 C 0.3656(5) 0.3272(5) 0.3602(5) 0.0240(13) Uani 1 1 d . . .
H25 H 0.4113 0.3697 0.4167 0.029 Uiso 1 1 calc R A .
C26 C 0.1877(3) 0.3566(2) 0.0737(2) 0.0296(15) Uani 1 1 d . A 1
F14 F 0.2147(3) 0.3011(3) 0.0031(2) 0.046(2) Uani 0.638(12) 1 d PR A 1
F15 F 0.0923(3) 0.3474(2) 0.0362(2) 0.077(5) Uani 0.638(12) 1 d PR A 1
F16 F 0.2196(3) 0.4506(3) 0.0650(2) 0.036(2) Uani 0.638(12) 1 d PRU A 1
F24 F 0.0977(3) 0.4183(3) 0.0706(2) 0.037(4) Uani 0.362(12) 1 d PR A 1
F25 F 0.1378(3) 0.2984(3) -0.0057(2) 0.066(7) Uani 0.362(12) 1 d PR A 1
F26 F 0.2291(3) 0.4357(3) 0.0478(2) 0.105(9) Uani 0.362(12) 1 d PR A 1


_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
O1 C6 1.221(7) . ?
N1 C5 1.334(8) . ?
N1 C1 1.347(7) . ?
N2 C6 1.380(7) . ?
N2 C3 1.393(7) . ?
N2 H2A 0.8800 . ?
N3 C6 1.368(6) . ?
N3 C7 1.399(7) . ?
N3 H3 0.8800 . ?
C1 C2 1.381(8) . ?
C1 H1 0.9500 . ?
C2 C3 1.395(8) . ?
C2 H2B 0.9500 . ?
C3 C4 1.402(8) . ?
C4 C5 1.370(8) . ?
C4 H4 0.9500 . ?
C5 H5 0.9500 . ?
C7 C12 1.381(8) . ?
C7 C8 1.401(7) . ?
C8 C9 1.378(8) . ?
C8 H8 0.9500 . ?
C9 C10 1.380(8) . ?
C9 H9 0.9500 . ?
C10 C11 1.389(7) . ?
C10 C13 1.493(8) . ?
C11 C12 1.375(8) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C13 F22 1.242(12) . ?
C13 F12 1.271(10) . ?
C13 F11 1.292(18) . ?
C13 F23 1.315(17) . ?
C13 F13 1.409(11) . ?
C13 F21 1.470(15) . ?
F12 F21 1.005(13) . ?
F12 F22 1.30(2) . ?
F13 F22 0.90(3) . ?
O2 C19 1.211(7) . ?
N4 C14 1.340(8) . ?
N4 C18 1.343(7) . ?
N5 C19 1.379(7) . ?
N5 C16 1.391(7) . ?
N5 H5A 0.8800 . ?
N6 C19 1.382(7) . ?
N6 C20 1.399(7) . ?
N6 H6 0.8800 . ?
C21 C22 1.392(8) . ?
C21 C20 1.413(8) . ?
C21 H21 0.9500 . ?
C14 C15 1.395(8) . ?
C14 H14 0.9500 . ?
C15 C16 1.390(7) . ?
C15 H15 0.9500 . ?
C16 C17 1.395(8) . ?
C17 C18 1.374(8) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
C20 C25 1.403(8) . ?
C22 C23 1.395(8) . ?
C22 H22 0.9500 . ?
C23 C24 1.390(8) . ?
C23 C26 1.480(6) . ?
C24 C25 1.383(8) . ?
C24 H24 0.9500 . ?
C25 H25 0.9500 . ?
C26 F15 1.245(3) . ?
C26 F25 1.275(3) . ?
C26 F26 1.307(3) . ?
C26 F16 1.307(3) . ?
C26 F14 1.426(3) . ?
C26 F24 1.507(3) . ?
F14 F25 1.065(2) . ?
F15 F24 1.013(2) . ?
F15 F25 1.242(3) . ?

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
C5 N1 C1 114.9(5) . . ?
C6 N2 C3 126.4(5) . . ?
C6 N2 H2A 116.8 . . ?
C3 N2 H2A 116.8 . . ?
C6 N3 C7 127.5(5) . . ?
C6 N3 H3 116.3 . . ?
C7 N3 H3 116.3 . . ?
N1 C1 C2 124.1(6) . . ?
N1 C1 H1 117.9 . . ?
C2 C1 H1 117.9 . . ?
C1 C2 C3 119.3(5) . . ?
C1 C2 H2B 120.4 . . ?
C3 C2 H2B 120.4 . . ?
N2 C3 C2 118.7(5) . . ?
N2 C3 C4 123.9(5) . . ?
C2 C3 C4 117.4(5) . . ?
C5 C4 C3 117.8(6) . . ?
C5 C4 H4 121.1 . . ?
C3 C4 H4 121.1 . . ?
N1 C5 C4 126.4(6) . . ?
N1 C5 H5 116.8 . . ?
C4 C5 H5 116.8 . . ?
O1 C6 N3 124.5(6) . . ?
O1 C6 N2 124.2(5) . . ?
N3 C6 N2 111.4(5) . . ?
C12 C7 N3 125.1(5) . . ?
C12 C7 C8 118.3(5) . . ?
N3 C7 C8 116.6(5) . . ?
C9 C8 C7 120.5(5) . . ?
C9 C8 H8 119.7 . . ?
C7 C8 H8 119.7 . . ?
C8 C9 C10 120.2(6) . . ?
C8 C9 H9 119.9 . . ?
C10 C9 H9 119.9 . . ?
C9 C10 C11 119.8(6) . . ?
C9 C10 C13 120.5(5) . . ?
C11 C10 C13 119.8(6) . . ?
C12 C11 C10 119.7(6) . . ?
C12 C11 H11 120.2 . . ?
C10 C11 H11 120.1 . . ?
C11 C12 C7 121.4(5) . . ?
C11 C12 H12 119.3 . . ?
C7 C12 H12 119.3 . . ?
F12 C13 F11 114.5(12) . . ?
F22 C13 F23 111.0(14) . . ?
F12 C13 F13 101.6(9) . . ?
F11 C13 F13 102.5(11) . . ?
F22 C13 F21 101.8(12) . . ?
F23 C13 F21 94.7(10) . . ?
F22 C13 C10 120.4(7) . . ?
F12 C13 C10 115.0(6) . . ?
F11 C13 C10 114.2(10) . . ?
F23 C13 C10 115.7(10) . . ?
F13 C13 C10 107.0(7) . . ?
F21 C13 C10 108.9(6) . . ?
C14 N4 C18 115.4(5) . . ?
C19 N5 C16 126.2(5) . . ?
C19 N5 H5A 116.9 . . ?
C16 N5 H5A 116.9 . . ?
C19 N6 C20 126.9(5) . . ?
C19 N6 H6 116.5 . . ?
C20 N6 H6 116.5 . . ?
C22 C21 C20 118.8(5) . . ?
C22 C21 H21 120.6 . . ?
C20 C21 H21 120.6 . . ?
N4 C14 C15 124.7(6) . . ?
N4 C14 H14 117.7 . . ?
C15 C14 H14 117.6 . . ?
C16 C15 C14 118.8(6) . . ?
C16 C15 H15 120.6 . . ?
C14 C15 H15 120.6 . . ?
C15 C16 N5 123.6(6) . . ?
C15 C16 C17 116.9(5) . . ?
N5 C16 C17 119.4(5) . . ?
C18 C17 C16 119.9(5) . . ?
C18 C17 H17 120.0 . . ?
C16 C17 H17 120.1 . . ?
N4 C18 C17 124.3(6) . . ?
N4 C18 H18 117.8 . . ?
C17 C18 H18 117.9 . . ?
O2 C19 N5 124.9(5) . . ?
O2 C19 N6 124.7(6) . . ?
N5 C19 N6 110.3(5) . . ?
N6 C20 C25 116.7(5) . . ?
N6 C20 C21 123.7(5) . . ?
C25 C20 C21 119.5(5) . . ?
C21 C22 C23 121.2(6) . . ?
C21 C22 H22 119.4 . . ?
C23 C22 H22 119.4 . . ?
C24 C23 C22 119.7(6) . . ?
C24 C23 C26 120.1(5) . . ?
C22 C23 C26 120.2(5) . . ?
C25 C24 C23 120.1(5) . . ?
C25 C24 H24 120.0 . . ?
C23 C24 H24 120.0 . . ?
C24 C25 C20 120.7(6) . . ?
C24 C25 H25 119.7 . . ?
C20 C25 H25 119.7 . . ?
F25 C26 F26 109.9 . . ?
F15 C26 F16 114.6 . . ?
F15 C26 F14 104.7 . . ?
F16 C26 F14 99.3 . . ?
F15 C26 C23 114.4(3) . . ?
F25 C26 C23 120.5(3) . . ?
F26 C26 C23 118.5(3) . . ?
F16 C26 C23 113.9(3) . . ?
F14 C26 C23 108.0(3) . . ?
F25 C26 F24 98.0 . . ?
F26 C26 F24 95.4 . . ?
C23 C26 F24 109.2(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
C5 N1 C1 C2 -0.9(9) . . . . ?
N1 C1 C2 C3 1.6(10) . . . . ?
C6 N2 C3 C2 -164.0(6) . . . . ?
C6 N2 C3 C4 18.4(10) . . . . ?
C1 C2 C3 N2 -178.7(6) . . . . ?
C1 C2 C3 C4 -0.9(9) . . . . ?
N2 C3 C4 C5 177.3(6) . . . . ?
C2 C3 C4 C5 -0.3(9) . . . . ?
C1 N1 C5 C4 -0.4(10) . . . . ?
C3 C4 C5 N1 1.0(10) . . . . ?
C7 N3 C6 O1 -8.0(10) . . . . ?
C7 N3 C6 N2 172.6(5) . . . . ?
C3 N2 C6 O1 0.9(10) . . . . ?
C3 N2 C6 N3 -179.7(6) . . . . ?
C6 N3 C7 C12 -2.1(9) . . . . ?
C6 N3 C7 C8 178.6(6) . . . . ?
C12 C7 C8 C9 0.2(9) . . . . ?
N3 C7 C8 C9 179.6(5) . . . . ?
C7 C8 C9 C10 -1.4(9) . . . . ?
C8 C9 C10 C11 1.3(9) . . . . ?
C8 C9 C10 C13 -178.1(5) . . . . ?
C9 C10 C11 C12 0.0(9) . . . . ?
C13 C10 C11 C12 179.4(6) . . . . ?
C10 C11 C12 C7 -1.2(9) . . . . ?
N3 C7 C12 C11 -178.2(6) . . . . ?
C8 C7 C12 C11 1.1(9) . . . . ?
C9 C10 C13 F22 -161(2) . . . . ?
C11 C10 C13 F22 20(2) . . . . ?
C9 C10 C13 F12 127.9(14) . . . . ?
C11 C10 C13 F12 -51.6(15) . . . . ?
C9 C10 C13 F11 -7.5(14) . . . . ?
C11 C10 C13 F11 173.1(12) . . . . ?
C9 C10 C13 F23 -22.6(14) . . . . ?
C11 C10 C13 F23 158.0(12) . . . . ?
C9 C10 C13 F13 -120.2(7) . . . . ?
C11 C10 C13 F13 60.4(8) . . . . ?
C9 C10 C13 F21 82.5(11) . . . . ?
C11 C10 C13 F21 -96.9(11) . . . . ?
F22 C13 F12 F21 156.2(13) . . . . ?
F11 C13 F12 F21 44.2(13) . . . . ?
F23 C13 F12 F21 57.4(15) . . . . ?
F13 C13 F12 F21 153.8(9) . . . . ?
C10 C13 F12 F21 -91.0(11) . . . . ?
F11 C13 F12 F22 -112.0(14) . . . . ?
F23 C13 F12 F22 -98.8(16) . . . . ?
F13 C13 F12 F22 -2.4(13) . . . . ?
F21 C13 F12 F22 -156.2(13) . . . . ?
C10 C13 F12 F22 112.8(9) . . . . ?
F12 C13 F13 F22 3.4(18) . . . . ?
F11 C13 F13 F22 122.0(17) . . . . ?
F23 C13 F13 F22 125.7(16) . . . . ?
F21 C13 F13 F22 30(2) . . . . ?
C10 C13 F13 F22 -117.6(14) . . . . ?
F22 F12 F21 C13 27.1(11) . . . . ?
F22 C13 F21 F12 -21.4(13) . . . . ?
F11 C13 F21 F12 -140.2(13) . . . . ?
F23 C13 F21 F12 -134.1(13) . . . . ?
F13 C13 F21 F12 -40.0(14) . . . . ?
C10 C13 F21 F12 106.8(10) . . . . ?
C13 F13 F22 F12 -5(3) . . . . ?
F12 C13 F22 F13 -176(2) . . . . ?
F11 C13 F22 F13 -72.3(17) . . . . ?
F23 C13 F22 F13 -60.4(15) . . . . ?
F21 C13 F22 F13 -160.2(14) . . . . ?
C10 C13 F22 F13 79(2) . . . . ?
F11 C13 F22 F12 104.0(17) . . . . ?
F23 C13 F22 F12 115.9(15) . . . . ?
F13 C13 F22 F12 176(2) . . . . ?
F21 C13 F22 F12 16.1(10) . . . . ?
C10 C13 F22 F12 -104.3(9) . . . . ?
F21 F12 F22 F13 -26(4) . . . . ?
C13 F12 F22 F13 6(3) . . . . ?
F21 F12 F22 C13 -32.0(13) . . . . ?
C18 N4 C14 C15 -0.4(9) . . . . ?
N4 C14 C15 C16 -0.4(10) . . . . ?
C14 C15 C16 N5 -177.6(6) . . . . ?
C14 C15 C16 C17 0.5(9) . . . . ?
C19 N5 C16 C15 -18.4(10) . . . . ?
C19 N5 C16 C17 163.5(6) . . . . ?
C15 C16 C17 C18 0.1(9) . . . . ?
N5 C16 C17 C18 178.3(6) . . . . ?
C14 N4 C18 C17 1.2(9) . . . . ?
C16 C17 C18 N4 -1.0(10) . . . . ?
C16 N5 C19 O2 -1.0(10) . . . . ?
C16 N5 C19 N6 179.5(6) . . . . ?
C20 N6 C19 O2 7.6(10) . . . . ?
C20 N6 C19 N5 -172.9(6) . . . . ?
C19 N6 C20 C25 -177.2(6) . . . . ?
C19 N6 C20 C21 4.4(10) . . . . ?
C22 C21 C20 N6 178.0(6) . . . . ?
C22 C21 C20 C25 -0.4(9) . . . . ?
C20 C21 C22 C23 -0.3(9) . . . . ?
C21 C22 C23 C24 0.6(10) . . . . ?
C21 C22 C23 C26 -179.0(5) . . . . ?
C22 C23 C24 C25 -0.3(10) . . . . ?
C26 C23 C24 C25 179.4(5) . . . . ?
C23 C24 C25 C20 -0.4(10) . . . . ?
N6 C20 C25 C24 -177.8(6) . . . . ?
C21 C20 C25 C24 0.8(10) . . . . ?
C24 C23 C26 F15 -122.5(5) . . . . ?
C22 C23 C26 F15 57.2(6) . . . . ?
C24 C23 C26 F25 170.4(4) . . . . ?
C22 C23 C26 F25 -9.9(7) . . . . ?
C24 C23 C26 F26 30.1(7) . . . . ?
C22 C23 C26 F26 -150.3(5) . . . . ?
C24 C23 C26 F16 12.0(7) . . . . ?
C22 C23 C26 F16 -168.3(5) . . . . ?
C24 C23 C26 F14 121.4(5) . . . . ?
C22 C23 C26 F14 -59.0(6) . . . . ?
C24 C23 C26 F24 -77.5(6) . . . . ?
C22 C23 C26 F24 102.1(6) . . . . ?
F15 C26 F14 F25 -7.1 . . . . ?
F26 C26 F14 F25 -127.1 . . . . ?
F16 C26 F14 F25 -125.8 . . . . ?
C23 C26 F14 F25 115.2(3) . . . . ?
F24 C26 F14 F25 -37.3 . . . . ?
F25 C26 F15 F24 -155.9 . . . . ?
F26 C26 F15 F24 -59.8 . . . . ?
F16 C26 F15 F24 -42.2 . . . . ?
F14 C26 F15 F24 -149.9 . . . . ?
C23 C26 F15 F24 92.0(3) . . . . ?
F26 C26 F15 F25 96.0 . . . . ?
F16 C26 F15 F25 113.7 . . . . ?
F14 C26 F15 F25 5.9 . . . . ?
C23 C26 F15 F25 -112.1(3) . . . . ?
F24 C26 F15 F25 155.9 . . . . ?
F25 F15 F24 C26 -32.4 . . . . ?
F25 C26 F24 F15 20.7 . . . . ?
F26 C26 F24 F15 131.8 . . . . ?
F16 C26 F24 F15 142.0 . . . . ?
F14 C26 F24 F15 46.9 . . . . ?
C23 C26 F24 F15 -105.5(3) . . . . ?
C26 F14 F25 F15 9.4 . . . . ?
F24 F15 F25 F14 26.5 . . . . ?
C26 F15 F25 F14 -10.6 . . . . ?
F24 F15 F25 C26 37.1 . . . . ?
F15 C26 F25 F14 172.0 . . . . ?
F26 C26 F25 F14 57.3 . . . . ?
F16 C26 F25 F14 70.5 . . . . ?
C23 C26 F25 F14 -86.1(3) . . . . ?
F24 C26 F25 F14 156.0 . . . . ?
F26 C26 F25 F15 -114.7 . . . . ?
F16 C26 F25 F15 -101.5 . . . . ?
F14 C26 F25 F15 -172.0 . . . . ?
C23 C26 F25 F15 101.9(3) . . . . ?
F24 C26 F25 F15 -16.0 . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H2A N1 0.88 2.28 3.100(6) 154.9 2_544
N3 H3 N1 0.88 2.31 3.101(7) 149.4 2_544
N3 H3 F15 0.88 2.56 3.195(6) 129.8 3_565
N5 H5A N4 0.88 2.27 3.098(6) 155.8 2_656
N6 H6 N4 0.88 2.28 3.081(7) 151.0 2_656
N6 H6 F12 0.88 2.55 3.142(15) 125.5 3_666

_diffrn_measured_fraction_theta_max 0.991
_diffrn_reflns_theta_full        27.50
_diffrn_measured_fraction_theta_full 0.991
_refine_diff_density_max         0.452
_refine_diff_density_min         -0.302
_refine_diff_density_rms         0.064
_database_code_depnum_ccdc_archive 'CCDC 1002415'
