# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry A.
# 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_aks59
_audit_creation_date             2012-06-22
_audit_creation_method           
;
  Olex2 1.1
  (compiled 2011.11.01 svn.r2039, GUI svn.r3906)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         '0.11(C20 H16 F6 N6)'
_chemical_formula_sum            'C H F N'
_chemical_formula_weight         46.03
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H N F'
_chemical_oxdiff_usercomment     Sudheer
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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x, -y-1/2, z-1/2'

_cell_length_a                   7.7969(6)
_cell_length_b                   12.0686(7)
_cell_length_c                   10.9819(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 103.056(6)
_cell_angle_gamma                90.00
_cell_volume                     1006.66(11)
_cell_formula_units_Z            19
_cell_measurement_reflns_used    1291
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.8935
_cell_measurement_theta_min      2.9114
_exptl_absorpt_coefficient_mu    0.157
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.92734
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.443
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       ?
_exptl_crystal_F_000             437
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0202
_diffrn_reflns_av_unetI/netI     0.0299
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            4064
_diffrn_reflns_theta_full        28.96
_diffrn_reflns_theta_max         28.96
_diffrn_reflns_theta_min         3.17
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 16.3291
_diffrn_measured_fraction_theta_full 0.859
_diffrn_measured_fraction_theta_max 0.859
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -47.00    1.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -       18.8566  -57.0000 -180.0000 48

#__ type_ start__ end____ width___ exp.time_
  2 omega  -33.00   76.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -       18.8566    0.0000 -180.0000 109

#__ type_ start__ end____ width___ exp.time_
  3 omega  -12.00   38.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -       18.8566  -57.0000  -60.0000 50
;
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0773476000
_diffrn_orient_matrix_UB_12      -0.0152412000
_diffrn_orient_matrix_UB_13      0.0196890000
_diffrn_orient_matrix_UB_21      -0.0520955000
_diffrn_orient_matrix_UB_22      0.0275412000
_diffrn_orient_matrix_UB_23      -0.0525715000
_diffrn_orient_matrix_UB_31      -0.0051506000
_diffrn_orient_matrix_UB_32      -0.0496423000
_diffrn_orient_matrix_UB_33      -0.0352399000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                1548
_reflns_number_total             2291
_reflns_odcompleteness_completeness 99.77
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
XL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    
;
XS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_refine_diff_density_max         0.202
_refine_diff_density_min         -0.359
_refine_diff_density_rms         0.077
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     146
_refine_ls_number_reflns         2291
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0803
_refine_ls_R_factor_gt           0.0566
_refine_ls_restrained_S_all      1.075
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1559
_refine_ls_wR_factor_ref         0.1789
_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. 
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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
N1 N 0.91145(19) 0.20353(13) 0.03415(12) 0.0516(4) Uani 1 1 d . . .
C2 C 0.7518(2) 0.08474(15) -0.13043(15) 0.0497(4) Uani 1 1 d . . .
H2 H 0.7624 0.1387 -0.1887 0.060 Uiso 1 1 calc R . .
F3 F 0.6282(2) 0.05279(12) -0.37537(11) 0.1024(6) Uani 1 1 d . . .
C4 C 0.8216(2) 0.10247(14) -0.00538(14) 0.0474(4) Uani 1 1 d . . .
C5 C 0.6656(2) -0.01370(15) -0.16916(16) 0.0519(5) Uani 1 1 d . . .
C6 C 0.8057(3) 0.02226(17) 0.08100(16) 0.0587(5) Uani 1 1 d . . .
H6 H 0.8542 0.0334 0.1656 0.070 Uiso 1 1 calc R . .
C7 C 0.6443(2) -0.09473(15) -0.08372(18) 0.0563(5) Uani 1 1 d . . .
N8 N 0.9429(2) 0.23428(17) 0.15478(14) 0.0725(6) Uani 1 1 d . . .
N9 N 1.0300(3) 0.32706(17) 0.16545(16) 0.0784(6) Uani 1 1 d . . .
C10 C 0.7179(3) -0.07384(17) 0.0411(2) 0.0626(5) Uani 1 1 d . . .
H10 H 0.7073 -0.1272 0.1000 0.075 Uiso 1 1 calc R . .
F11 F 0.4210(2) -0.04146(16) -0.33514(14) 0.1181(7) Uani 1 1 d . . .
F12 F 0.6575(2) -0.11881(12) -0.35028(13) 0.1140(7) Uani 1 1 d . . .
C13 C 0.9792(3) 0.27896(16) -0.03143(17) 0.0626(5) Uani 1 1 d . . .
H13 H 0.9757 0.2781 -0.1166 0.075 Uiso 1 1 calc R . .
C14 C 0.5489(3) -0.20277(17) -0.1200(2) 0.0766(6) Uani 1 1 d . . .
H14A H 0.4339 -0.1880 -0.1709 0.115 Uiso 1 1 calc R . .
H14B H 0.5379 -0.2418 -0.0460 0.115 Uiso 1 1 calc R . .
H14C H 0.6142 -0.2472 -0.1663 0.115 Uiso 1 1 calc R . .
C15 C 1.0534(3) 0.35619(18) 0.05235(19) 0.0688(6) Uani 1 1 d . . .
H15 H 1.1114 0.4195 0.0348 0.083 Uiso 1 1 calc R . .
C16 C 0.5940(3) -0.03038(17) -0.3064(2) 0.0676(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
N1 C4 1.425(2) . ?
N1 N8 1.344(2) . ?
N1 C13 1.341(2) . ?
C2 C4 1.375(2) . ?
C2 C5 1.384(3) . ?
F3 C16 1.321(2) . ?
C4 C6 1.380(2) . ?
C5 C7 1.391(3) . ?
C5 C16 1.498(3) . ?
C6 C10 1.368(3) . ?
C7 C10 1.384(3) . ?
C7 C14 1.509(3) . ?
N8 N9 1.301(3) . ?
N9 C15 1.342(3) . ?
F11 C16 1.321(3) . ?
F12 C16 1.313(2) . ?
C13 C15 1.345(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
N8 N1 C4 120.29(15) . . ?
C13 N1 C4 130.08(14) . . ?
C13 N1 N8 109.60(16) . . ?
C4 C2 C5 119.73(17) . . ?
C2 C4 N1 119.61(15) . . ?
C2 C4 C6 120.03(18) . . ?
C6 C4 N1 120.35(15) . . ?
C2 C5 C7 121.33(16) . . ?
C2 C5 C16 118.01(17) . . ?
C7 C5 C16 120.66(18) . . ?
C10 C6 C4 119.36(17) . . ?
C5 C7 C14 123.78(18) . . ?
C10 C7 C5 116.98(18) . . ?
C10 C7 C14 119.24(19) . . ?
N9 N8 N1 107.57(17) . . ?
N8 N9 C15 108.62(17) . . ?
C6 C10 C7 122.53(19) . . ?
N1 C13 C15 105.29(17) . . ?
N9 C15 C13 108.91(19) . . ?
F3 C16 C5 113.40(17) . . ?
F11 C16 F3 105.53(18) . . ?
F11 C16 C5 112.5(2) . . ?
F12 C16 F3 105.36(19) . . ?
F12 C16 C5 113.13(17) . . ?
F12 C16 F11 106.22(19) . . ?

_database_code_depnum_ccdc_archive 'CCDC 949060'
#######################################################################
#
#                 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_ak
_audit_creation_date             2012-07-28
_audit_creation_method           
;
  Olex2 1.1
  (compiled 2011.11.01 svn.r2039, GUI svn.r3906)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         '0.13(C9 H6 Cl2 F3 N3), 0.13(C9 H4 Cl2 F3 N3)'
_chemical_formula_sum            'C H Cl F N'
_chemical_formula_weight         81.48
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H N F Cl'
_chemical_oxdiff_usercomment     sudheer
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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           7
_space_group_name_H-M_alt        'P 1 c 1'
_space_group_name_Hall           'P -2yc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 'x, -y, z+1/2'

_cell_length_a                   16.0332(12)
_cell_length_b                   6.8721(4)
_cell_length_c                   10.7030(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 105.264(7)
_cell_angle_gamma                90.00
_cell_volume                     1137.67(13)
_cell_formula_units_Z            16
_cell_measurement_reflns_used    1414
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.3154
_cell_measurement_theta_min      2.8391
_exptl_absorpt_coefficient_mu    1.071
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.98631
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.903
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       ?
_exptl_crystal_F_000             640
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0173
_diffrn_reflns_av_unetI/netI     0.0240
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            4462
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         2.96
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 16.3291
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   54.00   83.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -       18.7003  179.0000  150.0000 29

#__ type_ start__ end____ width___ exp.time_
  2 omega  -51.00   38.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -       18.7003  -19.0000   60.0000 89

#__ type_ start__ end____ width___ exp.time_
  3 omega  -54.00   49.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -       18.7003  -19.0000  150.0000 103
;
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0425126000
_diffrn_orient_matrix_UB_12      -0.0276734000
_diffrn_orient_matrix_UB_13      0.0006581000
_diffrn_orient_matrix_UB_21      0.0172099000
_diffrn_orient_matrix_UB_22      -0.0707437000
_diffrn_orient_matrix_UB_23      0.0481378000
_diffrn_orient_matrix_UB_31      0.0005643000
_diffrn_orient_matrix_UB_32      0.0698639000
_diffrn_orient_matrix_UB_33      0.0489787000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                2153
_reflns_number_total             2783
_reflns_odcompleteness_completeness 99.76
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
XL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_refine_diff_density_max         0.692
_refine_diff_density_min         -0.374
_refine_diff_density_rms         0.077
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.18(15)
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.586
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     307
_refine_ls_number_reflns         2783
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0854
_refine_ls_R_factor_gt           0.0688
_refine_ls_restrained_S_all      1.586
_refine_ls_shift/su_max          0.603
_refine_ls_shift/su_mean         0.113
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2048
_refine_ls_wR_factor_ref         0.2299
_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. 
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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
Cl1 Cl 0.79719(16) 0.4389(4) 0.7306(3) 0.0745(8) Uani 1 1 d . . .
Cl4 Cl 0.5468(2) -0.0831(4) 0.5426(3) 0.0854(9) Uani 1 1 d . . .
N4 N 0.7219(4) 0.0888(10) 0.5797(6) 0.0448(17) Uani 1 1 d . . .
C10 C 0.6651(6) 0.1978(13) 0.6397(8) 0.050(2) Uani 1 1 d . . .
C12 C 0.6339(7) 0.4681(15) 0.7590(11) 0.064(3) Uani 1 1 d . . .
H12 H 0.6512 0.5823 0.8052 0.076 Uiso 1 1 calc R . .
N6 N 0.7721(8) -0.0668(14) 0.6251(9) 0.086(3) Uani 1 1 d . . .
H6 H 0.7770 -0.1278 0.6969 0.103 Uiso 1 1 calc R . .
C22 C 0.7850(7) 0.0147(16) 0.4339(9) 0.063(3) Uani 1 1 d . . .
H22 H 0.8028 0.0133 0.3579 0.075 Uiso 1 1 calc R . .
C20 C 0.7256(7) 0.1426(14) 0.4608(8) 0.058(3) Uani 1 1 d . . .
H20 H 0.6955 0.2420 0.4091 0.069 Uiso 1 1 calc R . .
C13 C 0.5534(6) 0.4003(17) 0.7397(8) 0.059(3) Uani 1 1 d . . .
C11 C 0.6908(6) 0.3627(13) 0.7079(9) 0.051(2) Uani 1 1 d . . .
C15 C 0.5811(5) 0.1287(13) 0.6258(9) 0.050(2) Uani 1 1 d . . .
C14 C 0.5267(7) 0.2370(16) 0.6777(9) 0.066(3) Uani 1 1 d . . .
H14 H 0.4703 0.1948 0.6691 0.079 Uiso 1 1 calc R . .
N5 N 0.8127(8) -0.1049(15) 0.5322(11) 0.088(3) Uani 1 1 d . . .
H5 H 0.8510 -0.1941 0.5366 0.105 Uiso 1 1 calc R . .
C17 C 0.4919(8) 0.551(3) 0.7891(11) 0.107(6) Uani 1 1 d . . .
F4 F 0.4196(8) 0.529(3) 0.7295(17) 0.258(11) Uani 1 1 d . . .
Cl2 Cl 0.97526(14) 0.0628(4) 0.8494(3) 0.0760(9) Uani 1 1 d . . .
Cl3 Cl 1.22625(19) 0.5810(4) 1.0391(3) 0.0830(10) Uani 1 1 d . . .
N3 N 1.0522(5) 0.4125(11) 1.0005(7) 0.0491(18) Uani 1 1 d . . .
C6 C 1.1342(7) 0.0322(12) 0.8182(9) 0.049(2) Uani 1 1 d . . .
H6A H 1.1148 -0.0803 0.7711 0.059 Uiso 1 1 calc R . .
C4 C 1.1088(6) 0.3102(12) 0.9431(7) 0.0413(17) Uani 1 1 d . . .
C5 C 1.0788(6) 0.1385(12) 0.8727(9) 0.048(2) Uani 1 1 d . . .
C24 C 1.0001(7) 0.5588(14) 0.9550(9) 0.058(2) Uani 1 1 d . . .
H24 H 0.9896 0.6165 0.8738 0.070 Uiso 1 1 calc R . .
C1 C 1.2207(7) 0.0966(11) 0.8349(10) 0.054(2) Uani 1 1 d . . .
N7 N 1.0435(6) 0.3668(14) 1.1189(8) 0.067(2) Uani 1 1 d . . .
N8 N 0.9942(6) 0.4845(15) 1.1501(7) 0.068(2) Uani 1 1 d . . .
C3 C 1.1916(8) 0.3688(12) 0.9553(9) 0.059(3) Uani 1 1 d . . .
C2 C 1.2493(6) 0.2667(14) 0.9036(9) 0.057(2) Uani 1 1 d . . .
H2 H 1.3056 0.3108 0.9144 0.068 Uiso 1 1 calc R . .
C25 C 0.9654(8) 0.6063(18) 1.0525(9) 0.074(3) Uani 1 1 d . . .
H25 H 0.9273 0.7086 1.0515 0.088 Uiso 1 1 calc R . .
C9 C 1.2826(7) -0.0132(14) 0.7817(10) 0.059(2) Uani 1 1 d . . .
F7 F 0.4605(12) 0.4351(18) 0.875(2) 0.242(10) Uani 1 1 d . . .
F9 F 0.5232(6) 0.657(2) 0.8595(13) 0.232(8) Uani 1 1 d . . .
F11 F 1.2862(13) 0.030(2) 0.6832(15) 0.284(12) Uani 1 1 d . . .
F10 F 1.3450(7) -0.0883(15) 0.8787(10) 0.151(4) Uani 1 1 d . . .
F12 F 1.2605(7) -0.2090(11) 0.7612(12) 0.146(4) Uani 1 1 d . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C11 1.739(10) . ?
Cl4 C15 1.719(10) . ?
N4 C10 1.453(10) . ?
N4 N6 1.349(11) . ?
N4 C20 1.341(10) . ?
C10 C11 1.352(12) . ?
C10 C15 1.400(13) . ?
C12 C13 1.336(16) . ?
C12 C11 1.386(15) . ?
N6 N5 1.350(13) . ?
C22 C20 1.381(14) . ?
C22 N5 1.317(14) . ?
C13 C14 1.317(14) . ?
C13 C17 1.612(16) . ?
C15 C14 1.371(12) . ?
C17 F4 1.176(16) . ?
C17 F7 1.406(17) . ?
C17 F9 1.075(16) . ?
F4 F7 1.65(2) . ?
Cl2 C5 1.694(9) . ?
Cl3 C3 1.725(9) . ?
N3 C4 1.410(11) . ?
N3 C24 1.316(11) . ?
N3 N7 1.348(11) . ?
C6 C5 1.391(12) . ?
C6 C1 1.421(15) . ?
C4 C5 1.415(12) . ?
C4 C3 1.361(15) . ?
C24 C25 1.345(13) . ?
C1 C2 1.393(14) . ?
C1 C9 1.475(13) . ?
N7 N8 1.237(12) . ?
N8 C25 1.323(13) . ?
C3 C2 1.388(13) . ?
C9 F11 1.111(12) . ?
C9 F10 1.341(13) . ?
C9 F12 1.394(14) . ?

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
N6 N4 C10 129.2(7) . . ?
C20 N4 C10 117.8(7) . . ?
C20 N4 N6 112.9(7) . . ?
C11 C10 N4 122.2(9) . . ?
C11 C10 C15 119.3(8) . . ?
C15 C10 N4 118.4(8) . . ?
C13 C12 C11 117.8(10) . . ?
N5 N6 N4 104.2(8) . . ?
N5 C22 C20 109.6(8) . . ?
N4 C20 C22 103.2(7) . . ?
C12 C13 C17 112.0(10) . . ?
C14 C13 C12 123.3(10) . . ?
C14 C13 C17 124.5(10) . . ?
C10 C11 Cl1 118.4(7) . . ?
C10 C11 C12 120.8(9) . . ?
C12 C11 Cl1 120.7(8) . . ?
C10 C15 Cl4 120.6(6) . . ?
C14 C15 Cl4 121.3(7) . . ?
C14 C15 C10 118.1(8) . . ?
C13 C14 C15 120.6(10) . . ?
C22 N5 N6 110.0(9) . . ?
F4 C17 C13 109.9(12) . . ?
F4 C17 F7 79.0(17) . . ?
F7 C17 C13 102.0(13) . . ?
F9 C17 C13 116.9(11) . . ?
F9 C17 F4 132.8(15) . . ?
F9 C17 F7 96.2(14) . . ?
C17 F4 F7 56.6(12) . . ?
C24 N3 C4 129.7(7) . . ?
C24 N3 N7 108.2(8) . . ?
N7 N3 C4 122.0(7) . . ?
C5 C6 C1 119.5(8) . . ?
N3 C4 C5 118.7(8) . . ?
C3 C4 N3 122.3(7) . . ?
C3 C4 C5 118.9(8) . . ?
C6 C5 Cl2 119.1(7) . . ?
C6 C5 C4 119.8(9) . . ?
C4 C5 Cl2 121.1(6) . . ?
N3 C24 C25 104.5(9) . . ?
C6 C1 C9 121.7(8) . . ?
C2 C1 C6 120.2(8) . . ?
C2 C1 C9 118.1(9) . . ?
N8 N7 N3 109.5(7) . . ?
N7 N8 C25 108.4(8) . . ?
C4 C3 Cl3 118.2(7) . . ?
C4 C3 C2 123.3(8) . . ?
C2 C3 Cl3 118.5(8) . . ?
C3 C2 C1 118.2(9) . . ?
N8 C25 C24 109.2(9) . . ?
F11 C9 C1 116.1(10) . . ?
F11 C9 F10 128.5(13) . . ?
F11 C9 F12 100.4(13) . . ?
F10 C9 C1 109.8(9) . . ?
F10 C9 F12 81.8(8) . . ?
F12 C9 C1 112.7(8) . . ?
C17 F7 F4 44.3(8) . . ?

_database_code_depnum_ccdc_archive 'CCDC 949061'
#######################################################################
#
#                 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_M1

_audit_creation_method           SHELXL-97
_chemical_formula_moiety         ?
_chemical_formula_sum            'C9 H6 F N5 O2'
_chemical_formula_weight         235.19
_chemical_melting_point          ?
_chemical_name_common            ?
_chemical_name_systematic        ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
N N 0.0061 0.0033 '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'
O O 0.0106 0.0060 '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'
C C 0.0033 0.0016 '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 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
loop_
_symmetry_equiv_pos_as_xyz
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, y, z'
'x-1/2, -y-1/2, z-1/2'

_cell_angle_alpha                90.00
_cell_angle_beta                 97.370(9)
_cell_angle_gamma                90.00
_cell_formula_units_Z            1
_cell_length_a                   5.4767(5)
_cell_length_b                   24.405(2)
_cell_length_c                   7.9829(8)
_cell_measurement_reflns_used    1338
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.637
_cell_measurement_theta_min      3.061
_cell_volume                     1058.18(17)
_exptl_absorpt_coefficient_mu    0.030
_exptl_absorpt_correction_T_max  1.0
_exptl_absorpt_correction_T_min  0.91538
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
 CrysAlisPro, Oxford Diffraction Ltd.,
 Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET)
 (compiled Jan 5 2010,16:28:46)
 Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_F_000             120
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    0.369
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_special_details           ?
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 16.3291
_diffrn_measured_fraction_theta_full 0.865
_diffrn_measured_fraction_theta_max 0.865
_diffrn_measurement_details      
;
 1 omega 38.00 88.00 1.0000 55.0000
 omega____ theta____ kappa____ phi______ frames
 - 18.7003 179.0000 60.0000 50
 2 omega -24.00 90.00 1.0000 55.0000
 omega____ theta____ kappa____ phi______ frames
 - 18.7003 19.0000 120.0000 114
 3 omega 48.00 95.00 1.0000 55.0000
 omega____ theta____ kappa____ phi______ frames
 - 18.7003 -179.0000 -30.0000 47
;
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0721081
_diffrn_orient_matrix_UB_12      -0.0236002
_diffrn_orient_matrix_UB_13      0.0228068
_diffrn_orient_matrix_UB_21      0.0070215
_diffrn_orient_matrix_UB_22      -0.0054341
_diffrn_orient_matrix_UB_23      -0.0865582
_diffrn_orient_matrix_UB_31      0.1086417
_diffrn_orient_matrix_UB_32      0.0160569
_diffrn_orient_matrix_UB_33      0.0042205
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0257
_diffrn_reflns_av_sigmaI/netI    0.0601
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -4
_diffrn_reflns_number            4390
_diffrn_reflns_theta_full        28.70
_diffrn_reflns_theta_max         28.70
_diffrn_reflns_theta_min         3.07
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                1171
_reflns_number_total             2373
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
 CrysAlisPro, Oxford Diffraction Ltd.,
 Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET)
 (compiled Jan 5 2010,16:28:46)
;
_computing_data_collection       
;
 CrysAlisPro, Oxford Diffraction Ltd.,
 Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET)
 (compiled Jan 5 2010,16:28:46)
;
_computing_data_reduction        
;
 CrysAlisPro, Oxford Diffraction Ltd.,
 Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET)
 (compiled Jan 5 2010,16:28:46)
;
_computing_molecular_graphics    
;
 OLEX2: a complete structure solution, refinement and analysis program.
 Dolomanov et al., J. Appl. Cryst. (2009). 42, 339-341
;
_computing_publication_material  
;
 OLEX2: a complete structure solution, refinement and analysis program.
 Dolomanov et al., J. Appl. Cryst. (2009). 42, 339-341
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)/Bruker'
_refine_diff_density_max         0.626
_refine_diff_density_min         -0.413
_refine_diff_density_rms         0.052
_refine_ls_R_factor_all          0.1413
_refine_ls_R_factor_gt           0.0741
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.162
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         2373
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.162
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_wR_factor_gt          0.2063
_refine_ls_wR_factor_ref         0.2283
_refine_ls_weighting_details     
;
calc w=1/[σ²(Fo²)+(0.1000P)²+0.0000P] where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_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.
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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 0.7408(4) 0.04858(11) 0.8033(4) 0.0469(8) Uani 1 1 d . . .
C7 C 1.0318(6) 0.12611(12) 0.7881(4) 0.0416(8) Uani 1 1 d . . .
C6 C 1.1703(6) 0.16784(13) 0.8684(4) 0.0477(9) Uani 1 1 d . . .
H6 H 1.2780 0.1878 0.8110 0.057 Uiso 1 1 calc R . .
N3 N 0.4981(5) 0.04493(13) 0.8183(4) 0.0590(9) Uani 1 1 d . . .
N1 N 1.0485(7) 0.11875(12) 0.6068(4) 0.0581(8) Uani 1 1 d . . .
C2 C 0.8769(5) 0.09461(13) 0.8738(4) 0.0451(9) Uani 1 1 d . . .
O2 O 1.2331(6) 0.13572(12) 0.5543(4) 0.0811(9) Uani 1 1 d . . .
N4 N 0.4216(5) -0.00179(14) 0.7517(4) 0.0629(9) Uani 1 1 d . . .
C5 C 1.1476(6) 0.17971(14) 1.0347(4) 0.0506(9) Uani 1 1 d . . .
C3 C 0.8600(7) 0.10713(16) 1.0408(5) 0.0611(10) Uani 1 1 d . . .
H3 H 0.7580 0.0863 1.1005 0.073 Uiso 1 1 calc R . .
C4 C 0.9923(7) 0.15006(17) 1.1203(5) 0.0650(10) Uani 1 1 d . . .
H4 H 0.9756 0.1587 1.2317 0.078 Uiso 1 1 calc R . .
O1 O 0.8776(6) 0.09788(14) 0.5185(4) 0.0973(12) Uani 1 1 d . . .
C1 C 1.2940(9) 0.22520(19) 1.1209(6) 0.0726(12) Uani 1 1 d . . .
F3 F 1.4291(8) 0.25122(18) 1.0327(5) 0.181(2) Uani 1 1 d . . .
F2 F 1.4469(8) 0.20876(14) 1.2463(6) 0.1731(18) Uani 1 1 d . . .
F1 F 1.1668(7) 0.26071(17) 1.1868(7) 0.194(2) Uani 1 1 d . . .
C C 0.8160(6) 0.00348(14) 0.7299(5) 0.0587(11) Uani 1 1 d . . .
H H 0.9742 -0.0044 0.7063 0.070 Uiso 1 1 calc R . .
C0AA C 0.6131(6) -0.02815(16) 0.6974(5) 0.0603(10) Uani 1 1 d . . .
H0A H 0.6065 -0.0624 0.6460 0.072 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
N2 N3 1.352(3) . ?
N2 C2 1.424(4) . ?
N2 C 1.337(4) . ?
C7 C6 1.378(5) . ?
C7 N1 1.473(5) . ?
C7 C2 1.388(4) . ?
C6 C5 1.380(5) . ?
N3 N4 1.304(4) . ?
N1 O2 1.216(4) . ?
N1 O1 1.210(4) . ?
C2 C3 1.382(5) . ?
N4 C0AA 1.349(4) . ?
C5 C4 1.365(5) . ?
C5 C1 1.486(5) . ?
C3 C4 1.381(5) . ?
C1 F3 1.257(5) . ?
C1 F2 1.285(5) . ?
C1 F1 1.268(5) . ?
C C0AA 1.351(4) . ?

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
N2 C C0AA 105.2(3) . . ?
C7 C6 C5 119.4(3) . . ?
C7 C2 N2 124.4(3) . . ?
C6 C7 N1 116.6(3) . . ?
C6 C7 C2 121.0(3) . . ?
C6 C5 C1 119.5(3) . . ?
N3 N2 C2 119.2(3) . . ?
N3 N4 C0AA 109.0(3) . . ?
C2 C7 N1 122.4(3) . . ?
O2 N1 C7 117.1(3) . . ?
N4 N3 N2 106.8(3) . . ?
N4 C0AA C 108.7(3) . . ?
C5 C4 C3 119.7(4) . . ?
C3 C2 N2 117.3(3) . . ?
C3 C2 C7 118.3(3) . . ?
C4 C5 C6 120.6(3) . . ?
C4 C5 C1 119.9(4) . . ?
C4 C3 C2 121.0(3) . . ?
O1 N1 C7 118.9(3) . . ?
O1 N1 O2 123.9(3) . . ?
F3 C1 C5 116.1(4) . . ?
F3 C1 F2 102.8(5) . . ?
F3 C1 F1 106.4(5) . . ?
F2 C1 C5 112.8(4) . . ?
F1 C1 C5 114.3(4) . . ?
F1 C1 F2 103.2(4) . . ?
C N2 N3 110.3(3) . . ?
C N2 C2 130.4(3) . . ?
_database_code_depnum_ccdc_archive 'CCDC 949062'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_shelxl

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C4.50 H2 F2 N2 O'
_chemical_formula_weight         138.08

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

_cell_length_a                   6.4061(3)
_cell_length_b                   10.2430(6)
_cell_length_c                   16.3818(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1074.94(10)
_cell_formula_units_Z            8
_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    1.706
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             552
_exptl_absorpt_coefficient_mu    0.169
_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            2651
_diffrn_reflns_av_R_equivalents  0.0139
_diffrn_reflns_av_sigmaI/netI    0.0209
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         3.18
_diffrn_reflns_theta_max         25.00
_reflns_number_total             1740
_reflns_number_gt                1585
_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)+(0.0468P)²+0.1754P] 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       0.0017(19)
_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   -0.7(10)
_refine_ls_number_reflns         1740
_refine_ls_number_parameters     173
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0372
_refine_ls_R_factor_gt           0.0332
_refine_ls_wR_factor_ref         0.0892
_refine_ls_wR_factor_gt          0.0862
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_restrained_S_all      1.057
_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 0.2009(2) 0.04363(17) 0.02968(9) 0.0685(5) Uani 1 1 d . . .
N2 N 0.9058(3) 0.01734(15) 0.22033(10) 0.0385(4) Uani 1 1 d . . .
C2 C 0.6455(3) -0.0859(2) 0.13746(13) 0.0437(5) Uani 1 1 d . . .
H2 H 0.7100 -0.1657 0.1472 0.052 Uiso 1 1 calc R . .
C1 C 0.7212(3) 0.0269(2) 0.17221(12) 0.0379(5) Uani 1 1 d . . .
N3 N 1.0414(3) -0.0805(2) 0.20543(12) 0.0495(5) Uani 1 1 d . . .
N4 N 1.1910(3) -0.0702(2) 0.25887(13) 0.0541(5) Uani 1 1 d . . .
C6 C 0.6208(4) 0.1444(2) 0.16184(13) 0.0422(5) Uani 1 1 d . . .
H6 H 0.6714 0.2194 0.1870 0.051 Uiso 1 1 calc R . .
C3 C 0.4728(4) -0.0781(2) 0.08818(14) 0.0457(6) Uani 1 1 d . . .
C4 C 0.3724(3) 0.0385(2) 0.07579(13) 0.0470(6) Uani 1 1 d . . .
C5 C 0.4433(3) 0.1498(2) 0.11346(13) 0.0430(5) Uani 1 1 d . . .
N1 N 0.3924(4) -0.1995(2) 0.05232(15) 0.0618(6) Uani 1 1 d . . .
F3 F 0.3145(3) 0.31033(18) 0.02431(10) 0.0882(6) Uani 1 1 d . . .
O1 O 0.3998(4) -0.29722(19) 0.09379(15) 0.0798(6) Uani 1 1 d . . .
F4 F 0.1323(3) 0.26763(18) 0.12750(12) 0.0930(6) Uani 1 1 d . . .
F2 F 0.4137(3) 0.37335(16) 0.14076(14) 0.1043(8) Uani 1 1 d . . .
C8 C 1.1529(4) 0.0332(2) 0.30718(15) 0.0533(6) Uani 1 1 d . . .
H8 H 1.2373 0.0612 0.3499 0.064 Uiso 1 1 calc R . .
C7 C 0.3282(4) 0.2768(2) 0.10212(17) 0.0547(6) Uani 1 1 d . . .
C9 C 0.9720(4) 0.0898(2) 0.28360(15) 0.0515(6) Uani 1 1 d . . .
H9 H 0.9076 0.1627 0.3062 0.062 Uiso 1 1 calc R . .
O2 O 0.3282(5) -0.1952(2) -0.01673(15) 0.1062(9) 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 C4 1.334(3) . ?
N2 C9 1.343(3) . ?
N2 N3 1.348(2) . ?
N2 C1 1.425(3) . ?
C2 C3 1.372(3) . ?
C2 C1 1.376(3) . ?
C1 C6 1.375(3) . ?
N3 N4 1.302(3) . ?
N4 C8 1.344(3) . ?
C6 C5 1.387(3) . ?
C3 C4 1.371(3) . ?
C3 N1 1.469(3) . ?
C4 C5 1.374(3) . ?
C5 C7 1.506(3) . ?
N1 O2 1.205(3) . ?
N1 O1 1.211(3) . ?
F3 C7 1.323(3) . ?
F4 C7 1.325(3) . ?
F2 C7 1.295(3) . ?
C8 C9 1.352(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
C9 N2 N3 110.29(19) . . ?
C9 N2 C1 130.63(19) . . ?
N3 N2 C1 119.05(17) . . ?
C3 C2 C1 118.6(2) . . ?
C6 C1 C2 121.26(18) . . ?
C6 C1 N2 121.09(19) . . ?
C2 C1 N2 117.65(19) . . ?
N4 N3 N2 106.99(17) . . ?
N3 N4 C8 109.02(19) . . ?
C1 C6 C5 119.28(19) . . ?
C2 C3 C4 121.1(2) . . ?
C2 C3 N1 117.9(2) . . ?
C4 C3 N1 120.9(2) . . ?
F1 C4 C3 120.3(2) . . ?
F1 C4 C5 119.6(2) . . ?
C3 C4 C5 120.1(2) . . ?
C4 C5 C6 119.6(2) . . ?
C4 C5 C7 120.0(2) . . ?
C6 C5 C7 120.4(2) . . ?
O2 N1 O1 124.8(2) . . ?
O2 N1 C3 117.7(2) . . ?
O1 N1 C3 117.5(2) . . ?
N4 C8 C9 109.0(2) . . ?
F2 C7 F3 107.5(2) . . ?
F2 C7 F4 107.5(2) . . ?
F3 C7 F4 104.9(2) . . ?
F2 C7 C5 113.1(2) . . ?
F3 C7 C5 112.0(2) . . ?
F4 C7 C5 111.3(2) . . ?
N2 C9 C8 104.7(2) . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.170
_refine_diff_density_min         -0.158
_refine_diff_density_rms         0.031
_database_code_depnum_ccdc_archive 'CCDC 949063'
#######################################################################
#
#                 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_aks58
_audit_creation_date             2012-06-22
_audit_creation_method           
;
  Olex2 1.1
  (compiled 2011.11.01 svn.r2039, GUI svn.r3906)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         '0.13(C18 H8 Cl2 F6 N8 O4)'
_chemical_formula_sum            'C H Cl0.06 F N O'
_chemical_formula_weight         64.24
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H N O F'
_chemical_oxdiff_usercomment     Sudheer
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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x, -y-1/2, z-1/2'

_cell_length_a                   14.580(2)
_cell_length_b                   13.1345(19)
_cell_length_c                   5.7684(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.465(13)
_cell_angle_gamma                90.00
_cell_volume                     1104.7(2)
_cell_formula_units_Z            16
_cell_measurement_reflns_used    519
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.8381
_cell_measurement_theta_min      2.7883
_exptl_absorpt_coefficient_mu    0.229
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.33736
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.545
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       ?
_exptl_crystal_F_000             513
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0379
_diffrn_reflns_av_unetI/netI     0.1055
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            3107
_diffrn_reflns_theta_full        28.97
_diffrn_reflns_theta_max         28.97
_diffrn_reflns_theta_min         2.79
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 16.3291
_diffrn_measured_fraction_theta_full 0.716
_diffrn_measured_fraction_theta_max 0.716
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -32.00   86.00   1.0000   56.0000
omega____ theta____ kappa____ phi______ frames
    -       18.5441    0.0000   90.0000 118

#__ type_ start__ end____ width___ exp.time_
  2 omega  -25.00    0.00   1.0000   56.0000
omega____ theta____ kappa____ phi______ frames
    -      -18.7003  -99.0000 -180.0000 25
;
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0327735000
_diffrn_orient_matrix_UB_12      -0.0276079000
_diffrn_orient_matrix_UB_13      0.0666679000
_diffrn_orient_matrix_UB_21      -0.0218160000
_diffrn_orient_matrix_UB_22      -0.0462507000
_diffrn_orient_matrix_UB_23      -0.0319213000
_diffrn_orient_matrix_UB_31      0.0284697000
_diffrn_orient_matrix_UB_32      -0.0038664000
_diffrn_orient_matrix_UB_33      -0.0984846000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                933
_reflns_number_total             2092
_reflns_odcompleteness_completeness 84.25
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
XL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    
;
XS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_refine_diff_density_max         0.192
_refine_diff_density_min         -0.357
_refine_diff_density_rms         0.056
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.845
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         2092
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1342
_refine_ls_R_factor_gt           0.0651
_refine_ls_restrained_S_all      0.845
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1513
_refine_ls_wR_factor_ref         0.2132
_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. 
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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
Cl1 Cl 0.56309(10) 0.14933(13) 0.0321(3) 0.0733(6) Uani 1 1 d . . .
N2 N 0.7733(3) 0.1582(3) 0.1690(7) 0.0477(11) Uani 1 1 d . . .
F3 F 0.7211(3) -0.2050(3) -0.5357(5) 0.0829(11) Uani 1 1 d . . .
O4 O 0.8511(3) 0.1921(3) 0.1644(6) 0.0634(11) Uani 1 1 d . . .
F5 F 0.6632(3) -0.0927(3) -0.7560(5) 0.0867(12) Uani 1 1 d . . .
N6 N 0.8618(3) -0.0703(3) -0.4405(6) 0.0434(10) Uani 1 1 d . . .
O7 O 0.7200(3) 0.1697(3) 0.3294(6) 0.0693(12) Uani 1 1 d . . .
N8 N 0.9430(3) -0.1056(4) -0.7338(7) 0.0601(13) Uani 1 1 d . . .
C9 C 0.7422(3) 0.0951(4) -0.0280(8) 0.0409(11) Uani 1 1 d . . .
C10 C 0.6515(3) 0.0826(4) -0.0894(8) 0.0454(12) Uani 1 1 d . . .
C11 C 0.7892(3) -0.0240(4) -0.3203(8) 0.0436(12) Uani 1 1 d . . .
C12 C 0.9343(4) -0.1212(4) -0.3511(8) 0.0531(14) Uani 1 1 d . . .
H12 H 0.9468 -0.1368 -0.1968 0.064 Uiso 1 1 calc R . .
C13 C 0.6962(3) -0.0428(4) -0.3708(7) 0.0454(12) Uani 1 1 d . . .
C14 C 0.6665(4) -0.1240(5) -0.5364(9) 0.0607(15) Uani 1 1 d . . .
C15 C 0.8110(3) 0.0448(4) -0.1462(7) 0.0428(12) Uani 1 1 d . . .
H15 H 0.8721 0.0572 -0.1086 0.051 Uiso 1 1 calc R . .
C16 C 0.6300(3) 0.0120(4) -0.2601(8) 0.0498(13) Uani 1 1 d . . .
H16 H 0.5688 0.0016 -0.3004 0.060 Uiso 1 1 calc R . .
N17 N 0.8680(3) -0.0594(4) -0.6725(6) 0.0568(12) Uani 1 1 d . . .
F18 F 0.5833(3) -0.1578(3) -0.4893(7) 0.1049(15) Uani 1 1 d . . .
C19 C 0.9849(4) -0.1442(4) -0.5428(9) 0.0583(15) Uani 1 1 d . . .
H19 H 1.0396 -0.1807 -0.5420 0.070 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
Cl1 C10 1.713(5) . ?
N2 O4 1.220(5) . ?
N2 O7 1.222(5) . ?
N2 C9 1.475(6) . ?
F3 C14 1.329(6) . ?
F5 C14 1.332(6) . ?
N6 C11 1.409(6) . ?
N6 C12 1.350(6) . ?
N6 N17 1.349(5) . ?
N8 N17 1.302(6) . ?
N8 C19 1.354(7) . ?
C9 C10 1.376(6) . ?
C9 C15 1.385(6) . ?
C10 C16 1.387(7) . ?
C11 C13 1.406(7) . ?
C11 C15 1.386(6) . ?
C12 C19 1.368(7) . ?
C13 C14 1.494(7) . ?
C13 C16 1.367(6) . ?
C14 F18 1.321(6) . ?

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
O4 N2 O7 124.7(4) . . ?
O4 N2 C9 117.9(4) . . ?
O7 N2 C9 117.4(4) . . ?
C12 N6 C11 128.0(4) . . ?
N17 N6 C11 120.0(4) . . ?
N17 N6 C12 111.9(4) . . ?
N17 N8 C19 109.1(4) . . ?
C10 C9 N2 123.6(5) . . ?
C10 C9 C15 121.0(5) . . ?
C15 C9 N2 115.4(4) . . ?
C9 C10 Cl1 124.0(4) . . ?
C9 C10 C16 118.2(5) . . ?
C16 C10 Cl1 117.8(4) . . ?
C13 C11 N6 123.3(4) . . ?
C15 C11 N6 118.0(4) . . ?
C15 C11 C13 118.7(5) . . ?
N6 C12 C19 103.1(4) . . ?
C11 C13 C14 122.2(5) . . ?
C16 C13 C11 119.6(5) . . ?
C16 C13 C14 118.2(5) . . ?
F3 C14 F5 105.5(5) . . ?
F3 C14 C13 113.5(5) . . ?
F5 C14 C13 113.3(5) . . ?
F18 C14 F3 106.3(5) . . ?
F18 C14 F5 105.8(5) . . ?
F18 C14 C13 111.8(5) . . ?
C9 C15 C11 120.3(5) . . ?
C13 C16 C10 121.8(5) . . ?
N8 N17 N6 106.5(4) . . ?
N8 C19 C12 109.4(5) . . ?

_database_code_depnum_ccdc_archive 'CCDC 949064'
#######################################################################
#
#                 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_p21n

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C11 H7 F3 N6'
_chemical_formula_weight         280.23

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'
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)/n  '

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                   7.445(2)
_cell_length_b                   15.889(5)
_cell_length_c                   10.638(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 109.220(5)
_cell_angle_gamma                90.00
_cell_volume                     1188.3(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    1963
_cell_measurement_theta_min      2.40
_cell_measurement_theta_max      21.96

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.19
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.566
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             568
_exptl_absorpt_coefficient_mu    0.136
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9643
_exptl_absorpt_correction_T_max  0.9747
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      273(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            11835
_diffrn_reflns_av_R_equivalents  0.0409
_diffrn_reflns_av_sigmaI/netI    0.0425
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.40
_diffrn_reflns_theta_max         25.80
_reflns_number_total             2270
_reflns_number_gt                1622
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0447P)²+0.2012P] 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         2270
_refine_ls_number_parameters     181
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0648
_refine_ls_R_factor_gt           0.0404
_refine_ls_wR_factor_ref         0.1073
_refine_ls_wR_factor_gt          0.0946
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_restrained_S_all      1.011
_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
N1 N 0.2284(2) 0.20450(9) 0.43504(14) 0.0438(4) Uani 1 1 d . . .
F1 F 0.19631(17) -0.07996(7) 0.78157(12) 0.0682(4) Uani 1 1 d . . .
F2 F 0.47887(19) -0.02955(8) 0.84372(12) 0.0755(4) Uani 1 1 d . . .
N3 N 0.2758(2) -0.13950(9) 0.55516(16) 0.0483(4) Uani 1 1 d . . .
F3 F 0.2428(2) 0.04974(8) 0.83121(12) 0.0849(5) Uani 1 1 d . . .
C1 C 0.2653(2) 0.09262(11) 0.59530(17) 0.0436(4) Uani 1 1 d . . .
H1 H 0.2720 0.1330 0.6600 0.052 Uiso 1 1 calc R . .
C2 C 0.2353(3) 0.05844(12) 0.37040(19) 0.0476(5) Uani 1 1 d . . .
H2 H 0.2222 0.0753 0.2841 0.057 Uiso 1 1 calc R . .
C3 C 0.2669(2) -0.05152(11) 0.53044(18) 0.0429(4) Uani 1 1 d . . .
C4 C 0.2435(2) 0.11739(11) 0.46711(17) 0.0414(4) Uani 1 1 d . . .
N4 N 0.1624(2) -0.19281(10) 0.46805(18) 0.0589(5) Uani 1 1 d . . .
C5 C 0.2771(2) 0.00822(11) 0.62886(18) 0.0427(4) Uani 1 1 d . . .
N5 N 0.1343(2) 0.22942(11) 0.30906(16) 0.0568(5) Uani 1 1 d . . .
N2 N 0.4029(2) -0.17531(10) 0.66076(17) 0.0569(5) Uani 1 1 d . . .
C6 C 0.2466(3) -0.02549(12) 0.40269(19) 0.0485(5) Uani 1 1 d . . .
H6 H 0.2405 -0.0654 0.3375 0.058 Uiso 1 1 calc R . .
N6 N 0.1396(3) 0.31136(11) 0.30811(17) 0.0622(5) Uani 1 1 d . . .
C7 C 0.2354(3) 0.33842(12) 0.4320(2) 0.0591(6) Uani 1 1 d . . .
H7 H 0.2587 0.3944 0.4574 0.071 Uiso 1 1 calc R . .
C8 C 0.2924(3) 0.27147(12) 0.51334(19) 0.0526(5) Uani 1 1 d . . .
H8 H 0.3611 0.2718 0.6039 0.063 Uiso 1 1 calc R . .
C9 C 0.2986(3) -0.01334(12) 0.7704(2) 0.0556(5) Uani 1 1 d . . .
C10 C 0.3668(3) -0.25589(13) 0.6406(2) 0.0617(6) Uani 1 1 d . . .
H10 H 0.4305 -0.2989 0.6971 0.074 Uiso 1 1 calc R . .
C11 C 0.2197(3) -0.26694(13) 0.5224(3) 0.0661(6) Uani 1 1 d . . .
H11 H 0.1690 -0.3185 0.4867 0.079 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
N1 C8 1.339(2) . ?
N1 N5 1.351(2) . ?
N1 C4 1.421(2) . ?
F1 C9 1.332(2) . ?
F2 C9 1.337(2) . ?
N3 N4 1.332(2) . ?
N3 N2 1.334(2) . ?
N3 C3 1.420(2) . ?
F3 C9 1.332(2) . ?
C1 C4 1.377(2) . ?
C1 C5 1.383(2) . ?
C1 H1 0.9300 . ?
C2 C6 1.373(2) . ?
C2 C4 1.378(3) . ?
C2 H2 0.9300 . ?
C3 C6 1.380(3) . ?
C3 C5 1.397(3) . ?
N4 C11 1.320(3) . ?
C5 C9 1.500(3) . ?
N5 N6 1.303(2) . ?
N2 C10 1.311(2) . ?
C6 H6 0.9300 . ?
N6 C7 1.346(3) . ?
C7 C8 1.349(3) . ?
C7 H7 0.9300 . ?
C8 H8 0.9300 . ?
C10 C11 1.380(3) . ?
C10 H10 0.9300 . ?
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
C8 N1 N5 110.27(15) . . ?
C8 N1 C4 129.87(15) . . ?
N5 N1 C4 119.85(15) . . ?
N4 N3 N2 115.21(15) . . ?
N4 N3 C3 121.12(15) . . ?
N2 N3 C3 123.55(15) . . ?
C4 C1 C5 120.63(17) . . ?
C4 C1 H1 119.7 . . ?
C5 C1 H1 119.7 . . ?
C6 C2 C4 119.33(18) . . ?
C6 C2 H2 120.3 . . ?
C4 C2 H2 120.3 . . ?
C6 C3 C5 119.71(17) . . ?
C6 C3 N3 117.42(16) . . ?
C5 C3 N3 122.86(16) . . ?
C1 C4 C2 120.47(17) . . ?
C1 C4 N1 119.36(16) . . ?
C2 C4 N1 120.16(16) . . ?
C11 N4 N3 102.89(17) . . ?
C1 C5 C3 118.85(17) . . ?
C1 C5 C9 117.20(16) . . ?
C3 C5 C9 123.95(16) . . ?
N6 N5 N1 107.06(15) . . ?
C10 N2 N3 103.20(16) . . ?
C2 C6 C3 121.00(17) . . ?
C2 C6 H6 119.5 . . ?
C3 C6 H6 119.5 . . ?
N5 N6 C7 108.63(16) . . ?
N6 C7 C8 109.26(18) . . ?
N6 C7 H7 125.4 . . ?
C8 C7 H7 125.4 . . ?
N1 C8 C7 104.78(17) . . ?
N1 C8 H8 127.6 . . ?
C7 C8 H8 127.6 . . ?
F3 C9 F1 105.99(18) . . ?
F3 C9 F2 106.01(17) . . ?
F1 C9 F2 106.77(15) . . ?
F3 C9 C5 111.61(15) . . ?
F1 C9 C5 113.31(17) . . ?
F2 C9 C5 112.63(18) . . ?
N2 C10 C11 109.37(19) . . ?
N2 C10 H10 125.3 . . ?
C11 C10 H10 125.3 . . ?
N4 C11 C10 109.33(19) . . ?
N4 C11 H11 125.3 . . ?
C10 C11 H11 125.3 . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        25.80
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.170
_refine_diff_density_min         -0.159
_refine_diff_density_rms         0.037
_database_code_depnum_ccdc_archive 'CCDC 949065'
#######################################################################
#
#                 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_sudheer167

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C H F N'
_chemical_formula_weight         46.03

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

_cell_length_a                   17.315(4)
_cell_length_b                   8.8212(18)
_cell_length_c                   19.147(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2924.4(10)
_cell_formula_units_Z            49
_cell_measurement_temperature    298(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    1.281
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1127
_exptl_absorpt_coefficient_mu    0.139
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(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            29357
_diffrn_reflns_av_R_equivalents  0.0843
_diffrn_reflns_av_sigmaI/netI    0.0655
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.13
_diffrn_reflns_theta_max         26.37
_reflns_number_total             5940
_reflns_number_gt                3795
_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+1.2978P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   2(2)
_refine_ls_number_reflns         5940
_refine_ls_number_parameters     451
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1394
_refine_ls_R_factor_gt           0.0904
_refine_ls_wR_factor_ref         0.2563
_refine_ls_wR_factor_gt          0.2220
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_restrained_S_all      1.021
_refine_ls_shift/su_max          0.003
_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
N24 N 0.3129(3) 0.3539(6) 0.0465(3) 0.0457(12) Uani 1 1 d . . .
N18 N 0.2712(3) 0.1042(6) -0.0417(2) 0.0456(12) Uani 1 1 d . . .
C14 C 0.3379(3) 0.0988(7) 0.0007(3) 0.0423(13) Uani 1 1 d . . .
C13 C 0.3820(3) -0.0284(7) -0.0035(3) 0.0463(15) Uani 1 1 d . . .
H13 H 0.3675 -0.1076 -0.0327 0.056 Uiso 1 1 calc R . .
C16 C 0.4263(4) 0.2061(7) 0.0840(3) 0.0448(14) Uani 1 1 d . . .
N19 N 0.2313(3) -0.0224(6) -0.0561(3) 0.0624(17) Uani 1 1 d . . .
C18 C 0.4700(4) 0.0767(7) 0.0806(3) 0.0474(14) Uani 1 1 d . . .
H18 H 0.5140 0.0669 0.1081 0.057 Uiso 1 1 calc R . .
N25 N 0.2441(3) 0.3536(7) 0.0779(3) 0.0536(13) Uani 1 1 d . . .
C17 C 0.4484(3) -0.0388(8) 0.0362(3) 0.0490(15) Uani 1 1 d . . .
C15 C 0.3592(3) 0.2206(7) 0.0438(3) 0.0393(13) Uani 1 1 d . . .
C27 C 0.3330(3) 0.4780(6) 0.0165(3) 0.0389(13) Uani 1 1 d . . .
H27 H 0.3784 0.4970 -0.0080 0.047 Uiso 1 1 calc R . .
C24 C 0.5276(4) 0.4701(8) 0.1762(4) 0.0573(17) Uani 1 1 d . . .
H24 H 0.5718 0.5197 0.1918 0.069 Uiso 1 1 calc R . .
N16 N 0.5265(3) 0.3620(6) 0.1307(3) 0.0536(13) Uani 1 1 d . . .
N17 N 0.2441(3) 0.2271(6) -0.0726(3) 0.0556(13) Uani 1 1 d . . .
N15 N 0.4055(3) 0.4071(6) 0.1679(3) 0.0589(15) Uani 1 1 d . . .
C20 C 0.1867(4) 0.1786(9) -0.1107(4) 0.0631(19) Uani 1 1 d . . .
H20 H 0.1564 0.2369 -0.1405 0.076 Uiso 1 1 calc R . .
N14 N 0.4519(2) 0.3237(6) 0.1273(3) 0.0435(11) Uani 1 1 d . . .
N26 N 0.2186(4) 0.4948(10) 0.0661(4) 0.085(2) Uani 1 1 d . . .
C19 C 0.1794(5) 0.0253(10) -0.0989(4) 0.078(2) Uani 1 1 d . . .
H19 H 0.1418 -0.0358 -0.1192 0.093 Uiso 1 1 calc R . .
C28 C 0.2770(5) 0.5701(9) 0.0274(4) 0.070(2) Uani 1 1 d . . .
H28 H 0.2749 0.6703 0.0124 0.084 Uiso 1 1 calc R . .
C23 C 0.4537(4) 0.5006(8) 0.1978(4) 0.0626(19) Uani 1 1 d . . .
H23 H 0.4400 0.5766 0.2291 0.075 Uiso 1 1 calc R . .
F2 F 0.4920(8) -0.2444(13) -0.0225(5) 0.243(7) Uani 1 1 d . . .
F1 F 0.5659(4) -0.1614(10) 0.0380(9) 0.255(8) Uani 1 1 d . . .
C4 C 0.0864(3) 0.3449(6) 0.3351(3) 0.0387(12) Uani 1 1 d . . .
N6 N 0.0186(3) 0.3501(5) 0.3769(2) 0.0406(11) Uani 1 1 d . . .
N21 N 0.0771(3) -0.0417(6) 0.3185(3) 0.0462(12) Uani 1 1 d . . .
C3 C 0.1048(3) 0.2197(7) 0.2940(3) 0.0401(13) Uani 1 1 d . . .
N3 N 0.1945(3) 0.0977(6) 0.2124(2) 0.0444(12) Uani 1 1 d . . .
N27 N 0.0551(3) 0.0920(5) 0.2919(2) 0.0407(11) Uani 1 1 d . . .
C26 C -0.0122(3) 0.0945(6) 0.2608(3) 0.0337(11) Uani 1 1 d . . .
H26 H -0.0357 0.1753 0.2381 0.040 Uiso 1 1 calc R . .
N5 N -0.0065(3) 0.2323(6) 0.4136(3) 0.0558(14) Uani 1 1 d . . .
C5 C 0.1346(3) 0.4720(7) 0.3354(3) 0.0424(13) Uani 1 1 d . . .
H5 H 0.1225 0.5556 0.3630 0.051 Uiso 1 1 calc R . .
N2 N 0.2697(3) 0.0626(6) 0.2046(3) 0.0519(13) Uani 1 1 d . . .
C2 C 0.1733(3) 0.2238(7) 0.2542(3) 0.0395(13) Uani 1 1 d . . .
N7 N -0.0165(3) 0.4792(6) 0.3887(3) 0.0607(15) Uani 1 1 d . . .
C6 C 0.1995(3) 0.4724(7) 0.2949(3) 0.0445(14) Uani 1 1 d . . .
N4 N 0.1467(3) 0.0149(7) 0.1750(3) 0.0601(15) Uani 1 1 d . . .
C1 C 0.2194(3) 0.3502(7) 0.2551(3) 0.0458(15) Uani 1 1 d . . .
H1 H 0.2643 0.3527 0.2285 0.055 Uiso 1 1 calc R . .
N23 N 0.0166(5) -0.1284(7) 0.3046(4) 0.084(2) Uani 1 1 d . . .
C29 C 0.2487(5) 0.6084(8) 0.2956(5) 0.0660(19) Uani 1 1 d . . .
C32 C -0.0385(4) -0.0434(9) 0.2693(3) 0.0555(17) Uani 1 1 d . . .
H32 H -0.0863 -0.0787 0.2541 0.067 Uiso 1 1 calc R . .
C9 C -0.0626(4) 0.2924(8) 0.4504(3) 0.0582(17) Uani 1 1 d . . .
H9 H -0.0928 0.2387 0.4820 0.070 Uiso 1 1 calc R . .
C12 C 0.1926(4) -0.0762(10) 0.1409(4) 0.073(2) Uani 1 1 d . . .
H12 H 0.1768 -0.1494 0.1091 0.088 Uiso 1 1 calc R . .
C10 C -0.0714(4) 0.4454(9) 0.4364(4) 0.0614(18) Uani 1 1 d . . .
H10 H -0.1075 0.5112 0.4558 0.074 Uiso 1 1 calc R . .
C11 C 0.2665(4) -0.0477(8) 0.1590(4) 0.0548(16) Uani 1 1 d . . .
H11 H 0.3092 -0.0993 0.1416 0.066 Uiso 1 1 calc R . .
F7 F 0.2782(5) 0.6408(7) 0.2341(4) 0.143(3) Uani 1 1 d . . .
F6 F 0.3141(4) 0.5840(9) 0.3256(5) 0.181(4) Uani 1 1 d . . .
F5 F 0.2196(4) 0.7240(8) 0.3187(8) 0.259(8) Uani 1 1 d . . .
F4 F 0.4798(8) -0.2737(13) 0.0698(9) 0.310(10) Uani 1 1 d . . .
C31 C 0.4954(4) -0.1787(9) 0.0321(5) 0.0665(19) 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
N24 C27 1.284(7) . ?
N24 N25 1.334(7) . ?
N24 C15 1.424(7) . ?
N18 N17 1.322(7) . ?
N18 N19 1.342(7) . ?
N18 C14 1.411(7) . ?
C14 C13 1.359(8) . ?
C14 C15 1.404(8) . ?
C13 C17 1.381(8) . ?
C16 C18 1.371(9) . ?
C16 C15 1.399(8) . ?
C16 N14 1.400(7) . ?
N19 C19 1.287(10) . ?
C18 C17 1.379(9) . ?
N25 N26 1.340(10) . ?
C17 C31 1.480(10) . ?
C27 C28 1.283(10) . ?
C24 N16 1.291(9) . ?
C24 C23 1.372(9) . ?
N16 N14 1.337(6) . ?
N17 C20 1.305(8) . ?
N15 C23 1.306(8) . ?
N15 N14 1.339(7) . ?
C20 C19 1.377(11) . ?
N26 C28 1.417(11) . ?
F2 C31 1.197(11) . ?
F1 C31 1.236(10) . ?
C4 C3 1.392(8) . ?
C4 C5 1.397(8) . ?
C4 N6 1.422(7) . ?
N6 N7 1.310(7) . ?
N6 N5 1.327(7) . ?
N21 N23 1.324(9) . ?
N21 N27 1.339(7) . ?
C3 C2 1.410(7) . ?
C3 N27 1.419(7) . ?
N3 N4 1.315(7) . ?
N3 N2 1.346(7) . ?
N3 C2 1.419(8) . ?
N27 C26 1.307(7) . ?
C26 C32 1.309(9) . ?
N5 C9 1.312(8) . ?
C5 C6 1.367(8) . ?
N2 C11 1.308(9) . ?
C2 C1 1.372(8) . ?
N7 C10 1.350(9) . ?
C6 C1 1.364(9) . ?
C6 C29 1.472(10) . ?
N4 C12 1.305(8) . ?
N23 C32 1.389(10) . ?
C29 F5 1.221(9) . ?
C29 F6 1.286(10) . ?
C29 F7 1.316(11) . ?
C9 C10 1.385(10) . ?
C12 C11 1.349(10) . ?
F4 C31 1.138(11) . ?

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
C27 N24 N25 116.4(5) . . ?
C27 N24 C15 122.3(5) . . ?
N25 N24 C15 121.1(5) . . ?
N17 N18 N19 114.0(5) . . ?
N17 N18 C14 125.2(5) . . ?
N19 N18 C14 120.8(5) . . ?
C13 C14 C15 121.2(5) . . ?
C13 C14 N18 117.0(5) . . ?
C15 C14 N18 121.8(6) . . ?
C14 C13 C17 119.4(6) . . ?
C18 C16 C15 120.6(5) . . ?
C18 C16 N14 118.0(5) . . ?
C15 C16 N14 121.4(6) . . ?
C19 N19 N18 102.7(6) . . ?
C16 C18 C17 119.6(6) . . ?
N24 N25 N26 102.5(6) . . ?
C18 C17 C13 121.1(6) . . ?
C18 C17 C31 119.9(6) . . ?
C13 C17 C31 119.0(6) . . ?
C16 C15 C14 118.1(5) . . ?
C16 C15 N24 121.5(5) . . ?
C14 C15 N24 120.4(5) . . ?
C28 C27 N24 105.2(6) . . ?
N16 C24 C23 109.5(5) . . ?
C24 N16 N14 103.6(5) . . ?
C20 N17 N18 104.6(6) . . ?
C23 N15 N14 102.5(5) . . ?
N17 C20 C19 107.5(7) . . ?
N16 N14 N15 114.4(5) . . ?
N16 N14 C16 121.5(5) . . ?
N15 N14 C16 124.1(4) . . ?
N25 N26 C28 106.8(6) . . ?
N19 C19 C20 111.2(6) . . ?
C27 C28 N26 109.1(7) . . ?
N15 C23 C24 109.9(6) . . ?
C3 C4 C5 120.2(5) . . ?
C3 C4 N6 122.2(5) . . ?
C5 C4 N6 117.6(5) . . ?
N7 N6 N5 115.9(5) . . ?
N7 N6 C4 120.6(5) . . ?
N5 N6 C4 122.8(5) . . ?
N23 N21 N27 102.0(5) . . ?
C4 C3 C2 118.6(5) . . ?
C4 C3 N27 120.4(5) . . ?
C2 C3 N27 121.0(5) . . ?
N4 N3 N2 114.9(5) . . ?
N4 N3 C2 125.4(5) . . ?
N2 N3 C2 119.6(5) . . ?
C26 N27 N21 116.2(5) . . ?
C26 N27 C3 122.7(5) . . ?
N21 N27 C3 121.0(5) . . ?
N27 C26 C32 103.8(5) . . ?
C9 N5 N6 102.1(5) . . ?
C6 C5 C4 119.3(6) . . ?
C11 N2 N3 101.8(5) . . ?
C1 C2 C3 120.2(5) . . ?
C1 C2 N3 119.6(5) . . ?
C3 C2 N3 120.2(5) . . ?
N6 N7 C10 104.6(6) . . ?
C1 C6 C5 121.5(6) . . ?
C1 C6 C29 120.3(6) . . ?
C5 C6 C29 118.2(6) . . ?
C12 N4 N3 103.3(5) . . ?
C6 C1 C2 120.2(5) . . ?
N21 N23 C32 109.2(6) . . ?
F5 C29 F6 110.0(10) . . ?
F5 C29 F7 107.7(9) . . ?
F6 C29 F7 95.5(8) . . ?
F5 C29 C6 116.5(7) . . ?
F6 C29 C6 112.2(7) . . ?
F7 C29 C6 113.1(7) . . ?
C26 C32 N23 108.8(6) . . ?
N5 C9 C10 111.8(6) . . ?
N4 C12 C11 109.6(6) . . ?
N7 C10 C9 105.6(6) . . ?
N2 C11 C12 110.4(6) . . ?
F4 C31 F2 100.7(12) . . ?
F4 C31 F1 105.5(12) . . ?
F2 C31 F1 100.8(11) . . ?
F4 C31 C17 116.8(8) . . ?
F2 C31 C17 115.0(8) . . ?
F1 C31 C17 115.8(7) . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        26.37
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.535
_refine_diff_density_min         -0.356
_refine_diff_density_rms         0.082
_database_code_depnum_ccdc_archive 'CCDC 949066'
#######################################################################
#
#                 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_aks57
_audit_creation_date             2012-06-22
_audit_creation_method           
;
  Olex2 1.1
  (compiled 2011.11.01 svn.r2039, GUI svn.r3906)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         '0.2(C13 H8 F3 N9)'
_chemical_formula_sum            'C H F N O'
_chemical_formula_weight         62.03
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H N O F'
_chemical_oxdiff_usercomment     'Sudheer Kumar'
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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, -y, -z'

_cell_length_a                   8.5034(13)
_cell_length_b                   10.042(2)
_cell_length_c                   10.289(2)
_cell_angle_alpha                61.31(2)
_cell_angle_beta                 84.601(15)
_cell_angle_gamma                72.454(16)
_cell_volume                     733.5(2)
_cell_formula_units_Z            10
_cell_measurement_reflns_used    1516
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.0658
_cell_measurement_theta_min      2.9288
_exptl_absorpt_coefficient_mu    0.158
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.75692
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.404
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       ?
_exptl_crystal_F_000             310
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0183
_diffrn_reflns_av_unetI/netI     0.0326
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            5501
_diffrn_reflns_theta_full        29.13
_diffrn_reflns_theta_max         29.13
_diffrn_reflns_theta_min         2.93
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 16.3291
_diffrn_measured_fraction_theta_full 0.830
_diffrn_measured_fraction_theta_max 0.830
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -52.00   44.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -       18.7003  -37.0000  -30.0000 96

#__ type_ start__ end____ width___ exp.time_
  2 omega  -36.00   31.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -       18.7003  -57.0000 -150.0000 67

#__ type_ start__ end____ width___ exp.time_
  3 omega   44.00   88.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -       18.7003 -179.0000   30.0000 44

#__ type_ start__ end____ width___ exp.time_
  4 omega   -4.00   85.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -       18.7003   37.0000  150.0000 89

#__ type_ start__ end____ width___ exp.time_
  5 omega  -14.00   22.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      -18.8566  -99.0000  120.0000 36

#__ type_ start__ end____ width___ exp.time_
  6 omega  -25.00   19.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      -18.8566  -99.0000  -60.0000 44
;
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0071656000
_diffrn_orient_matrix_UB_12      0.0732576000
_diffrn_orient_matrix_UB_13      -0.0653993000
_diffrn_orient_matrix_UB_21      0.0257395000
_diffrn_orient_matrix_UB_22      0.0298899000
_diffrn_orient_matrix_UB_23      0.0417096000
_diffrn_orient_matrix_UB_31      0.0834732000
_diffrn_orient_matrix_UB_32      -0.0288813000
_diffrn_orient_matrix_UB_33      -0.0134725000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                2253
_reflns_number_total             3281
_reflns_odcompleteness_completeness 99.63
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
XL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    
;
XS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_refine_diff_density_max         0.411
_refine_diff_density_min         -0.477
_refine_diff_density_rms         0.057
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.315
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     234
_refine_ls_number_reflns         3281
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0908
_refine_ls_R_factor_gt           0.0657
_refine_ls_restrained_S_all      1.315
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1979
_refine_ls_wR_factor_ref         0.2196
_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. 
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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
N1 N 0.7033(2) 0.1736(2) 0.2492(2) 0.0475(5) Uani 1 1 d . . .
C2 C 0.7477(3) -0.0788(3) 0.7130(3) 0.0471(6) Uani 1 1 d . . .
C3 C 0.8418(3) -0.1493(3) 0.6327(3) 0.0501(6) Uani 1 1 d . . .
H3 H 0.9136 -0.2516 0.6812 0.060 Uiso 1 1 calc R . .
N4 N 0.9250(2) -0.1412(2) 0.4010(2) 0.0529(6) Uani 1 1 d . . .
C5 C 0.8275(3) -0.0654(3) 0.4794(3) 0.0462(6) Uani 1 1 d . . .
C6 C 0.6288(3) 0.1564(3) 0.4902(3) 0.0462(6) Uani 1 1 d . . .
N7 N 0.7624(3) -0.1629(3) 0.8687(2) 0.0546(6) Uani 1 1 d . . .
C8 C 0.6418(3) 0.0723(3) 0.6425(3) 0.0488(6) Uani 1 1 d . . .
H8 H 0.5788 0.1178 0.6979 0.059 Uiso 1 1 calc R . .
C9 C 0.7207(3) 0.0879(3) 0.4061(3) 0.0440(6) Uani 1 1 d . . .
N13 N 0.7067(3) -0.0884(3) 0.9496(3) 0.0641(6) Uani 1 1 d . . .
N14 N 0.7687(3) 0.2923(3) 0.1712(2) 0.0610(6) Uani 1 1 d . . .
N16 N 0.6244(3) 0.1383(3) 0.1708(3) 0.0658(7) Uani 1 1 d . . .
N17 N 0.9753(3) -0.0643(3) 0.2658(3) 0.0653(7) Uani 1 1 d . . .
C18 C 0.5115(3) 0.3213(3) 0.4178(3) 0.0597(7) Uani 1 1 d . . .
N19 N 0.9766(3) -0.2987(3) 0.4610(3) 0.0762(8) Uani 1 1 d . . .
N21 N 0.7404(4) -0.2074(4) 1.0887(3) 0.0981(10) Uani 1 1 d . . .
C23 C 0.6375(4) 0.2437(4) 0.0334(3) 0.0714(9) Uani 1 1 d . . .
H23 H 0.5932 0.2531 -0.0509 0.086 Uiso 1 1 calc R . .
C24 C 0.7261(4) 0.3377(4) 0.0332(3) 0.0704(8) Uani 1 1 d . . .
H24 H 0.7518 0.4199 -0.0508 0.084 Uiso 1 1 calc R . .
C25 C 0.8152(5) -0.3495(5) 1.0813(4) 0.0803(10) Uani 1 1 d . . .
C1 C 1.0654(4) -0.1819(4) 0.2409(4) 0.0708(9) Uani 1 1 d . . .
C4 C 1.0665(4) -0.3223(4) 0.3585(4) 0.0792(10) Uani 1 1 d . . .
H4 H 1.1223 -0.4212 0.3662 0.095 Uiso 1 1 calc R . .
C7 C 0.8273(3) -0.3181(3) 0.9453(3) 0.0519(6) Uani 1 1 d . . .
H7 H 0.8721 -0.3892 0.9085 0.062 Uiso 1 1 calc R . .
F1 F 0.4164(2) 0.3509(2) 0.3069(2) 0.0853(6) Uani 1 1 d . . .
F2 F 0.4087(2) 0.3497(2) 0.5135(2) 0.0966(7) Uani 1 1 d . . .
F3 F 0.5872(3) 0.43213(19) 0.3638(2) 0.0922(7) Uani 1 1 d . . .
H1 H 1.118(5) -0.163(4) 0.159(4) 0.088(11) Uiso 1 1 d . . .
H25 H 0.854(4) -0.445(4) 1.154(4) 0.082(10) 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
N1 C9 1.415(3) . ?
N1 N14 1.331(3) . ?
N1 N16 1.321(3) . ?
C2 C3 1.386(3) . ?
C2 N7 1.404(3) . ?
C2 C8 1.372(3) . ?
C3 C5 1.382(4) . ?
N4 C5 1.415(3) . ?
N4 N17 1.330(3) . ?
N4 N19 1.330(3) . ?
C5 C9 1.391(3) . ?
C6 C8 1.374(3) . ?
C6 C9 1.397(3) . ?
C6 C18 1.500(3) . ?
N7 N13 1.337(3) . ?
N7 C7 1.319(3) . ?
N13 N21 1.337(4) . ?
N14 C24 1.316(4) . ?
N16 C23 1.317(4) . ?
N17 C1 1.325(4) . ?
C18 F1 1.322(3) . ?
C18 F2 1.331(3) . ?
C18 F3 1.316(3) . ?
N19 C4 1.316(4) . ?
N21 C25 1.413(5) . ?
C23 C24 1.372(4) . ?
C25 C7 1.279(4) . ?
C1 C4 1.345(5) . ?

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
N14 N1 C9 122.1(2) . . ?
N16 N1 C9 122.1(2) . . ?
N16 N1 N14 115.8(2) . . ?
C3 C2 N7 119.4(2) . . ?
C8 C2 C3 120.9(2) . . ?
C8 C2 N7 119.7(2) . . ?
C5 C3 C2 119.1(2) . . ?
N17 N4 C5 124.0(2) . . ?
N17 N4 N19 114.8(2) . . ?
N19 N4 C5 121.2(2) . . ?
C3 C5 N4 117.6(2) . . ?
C3 C5 C9 120.7(2) . . ?
C9 C5 N4 121.7(2) . . ?
C8 C6 C9 120.4(2) . . ?
C8 C6 C18 118.2(2) . . ?
C9 C6 C18 121.4(2) . . ?
N13 N7 C2 121.0(2) . . ?
C7 N7 C2 123.5(2) . . ?
C7 N7 N13 115.4(2) . . ?
C2 C8 C6 120.0(2) . . ?
C5 C9 N1 121.1(2) . . ?
C5 C9 C6 118.8(2) . . ?
C6 C9 N1 120.1(2) . . ?
N21 N13 N7 102.7(2) . . ?
C24 N14 N1 103.0(2) . . ?
C23 N16 N1 102.5(2) . . ?
C1 N17 N4 102.5(3) . . ?
F1 C18 C6 114.0(2) . . ?
F1 C18 F2 105.7(2) . . ?
F2 C18 C6 111.7(2) . . ?
F3 C18 C6 112.9(2) . . ?
F3 C18 F1 106.2(2) . . ?
F3 C18 F2 105.8(2) . . ?
C4 N19 N4 103.0(2) . . ?
N13 N21 C25 107.7(3) . . ?
N16 C23 C24 109.9(3) . . ?
N14 C24 C23 108.8(3) . . ?
C7 C25 N21 109.4(3) . . ?
N17 C1 C4 110.0(3) . . ?
N19 C4 C1 109.7(3) . . ?
C25 C7 N7 104.8(3) . . ?

_database_code_depnum_ccdc_archive 'CCDC 949067'
#######################################################################
#
#                 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_aks160

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C H F N O'
_chemical_formula_weight         62.03

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

_cell_length_a                   18.596(5)
_cell_length_b                   10.898(3)
_cell_length_c                   28.644(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.480(4)
_cell_angle_gamma                90.00
_cell_volume                     5805(3)
_cell_formula_units_Z            96
_cell_measurement_temperature    298(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    1.703
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2976
_exptl_absorpt_coefficient_mu    0.191
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(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            25472
_diffrn_reflns_av_R_equivalents  0.0940
_diffrn_reflns_av_sigmaI/netI    0.0578
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_theta_min         1.42
_diffrn_reflns_theta_max         26.05
_reflns_number_total             5726
_reflns_number_gt                4204
_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)+(0.1257P)²+4.0579P] 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       0.00012(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         5726
_refine_ls_number_parameters     452
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0814
_refine_ls_R_factor_gt           0.0650
_refine_ls_wR_factor_ref         0.2175
_refine_ls_wR_factor_gt          0.2038
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_restrained_S_all      1.063
_refine_ls_shift/su_max          0.154
_refine_ls_shift/su_mean         0.024

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
N8 N 0.23631(11) 0.32657(19) 0.40139(7) 0.0434(5) Uani 1 1 d . . .
C1A C 0.19101(13) 0.3175(2) 0.44124(8) 0.0413(6) Uani 1 1 d . . .
N3A N 0.05362(12) 0.28641(19) 0.55574(7) 0.0463(5) Uani 1 1 d . . .
C1 C 0.12457(14) 0.1926(2) 0.49531(9) 0.0455(6) Uani 1 1 d . . .
H1 H 0.1112 0.1157 0.5064 0.055 Uiso 1 1 calc R . .
C2 C 0.17035(14) 0.2028(2) 0.45748(8) 0.0422(6) Uani 1 1 d . . .
N13 N 0.02507(13) 0.1767(2) 0.56655(8) 0.0553(6) Uani 1 1 d . . .
C4 C 0.11828(14) 0.4126(2) 0.50082(9) 0.0479(6) Uani 1 1 d . . .
H4 H 0.1005 0.4827 0.5152 0.057 Uiso 1 1 calc R . .
N7 N 0.19409(12) 0.0923(2) 0.43667(8) 0.0493(5) Uani 1 1 d . . .
C5 C 0.09928(13) 0.2974(2) 0.51628(8) 0.0425(6) Uani 1 1 d . . .
F3 F 0.18018(13) 0.56126(19) 0.40104(7) 0.0933(7) Uani 1 1 d . . .
N6A N 0.30467(11) 0.3614(2) 0.40402(7) 0.0502(6) Uani 1 1 d . . .
F1 F 0.14311(14) 0.63364(17) 0.46496(8) 0.1049(9) Uani 1 1 d . . .
C7 C 0.16497(14) 0.4214(2) 0.46293(9) 0.0458(6) Uani 1 1 d . . .
N14 N -0.01125(14) 0.1907(2) 0.60497(9) 0.0615(7) Uani 1 1 d . . .
N5A N 0.21315(13) 0.2927(2) 0.35928(8) 0.0587(6) Uani 1 1 d . . .
N19A N 0.25918(14) 0.0765(2) 0.41894(10) 0.0659(7) Uani 1 1 d . . .
C11 C 0.32595(15) 0.3517(3) 0.36024(9) 0.0542(7) Uani 1 1 d . . .
H11 H 0.3717 0.3706 0.3495 0.065 Uiso 1 1 calc R . .
C10 C 0.15171(16) -0.0050(2) 0.43518(10) 0.0546(7) Uani 1 1 d . . .
H10 H 0.1049 -0.0122 0.4460 0.066 Uiso 1 1 calc R . .
C13 C 0.18526(19) 0.5484(3) 0.44705(11) 0.0647(9) Uani 1 1 d . . .
C14 C 0.27022(16) 0.3097(3) 0.33308(10) 0.0602(8) Uani 1 1 d . . .
H14 H 0.2723 0.2954 0.3011 0.072 Uiso 1 1 calc R . .
F2 F 0.25232(14) 0.5767(2) 0.45813(9) 0.1027(8) Uani 1 1 d . . .
C4A C 0.03501(17) 0.3707(3) 0.58724(10) 0.0630(8) Uani 1 1 d . . .
H4A H 0.0475 0.4533 0.5877 0.076 Uiso 1 1 calc R . .
C9 C 0.1906(2) -0.0879(3) 0.41522(13) 0.0772(10) Uani 1 1 d . . .
H9 H 0.1756 -0.1676 0.4088 0.093 Uiso 1 1 calc R . .
C3B C -0.00614(18) 0.3090(3) 0.61845(11) 0.0659(9) Uani 1 1 d . . .
H3B H -0.0273 0.3429 0.6448 0.079 Uiso 1 1 calc R . .
N20A N 0.2578(2) -0.0405(3) 0.40481(13) 0.0980(11) Uani 1 1 d . . .
N5 N 0.15109(11) 0.17742(18) 0.22568(7) 0.0417(5) Uani 1 1 d . . .
N6 N -0.00496(11) 0.21851(19) 0.39201(7) 0.0430(5) Uani 1 1 d . . .
N4 N 0.09826(11) 0.41197(19) 0.25769(7) 0.0456(5) Uani 1 1 d . . .
C2B C 0.04639(13) 0.3112(2) 0.32365(8) 0.0417(6) Uani 1 1 d . . .
H2B H 0.0301 0.3871 0.3339 0.050 Uiso 1 1 calc R . .
C19 C 0.03321(13) 0.2076(2) 0.34926(8) 0.0401(5) Uani 1 1 d . . .
C20 C 0.08430(13) 0.3020(2) 0.28232(8) 0.0403(5) Uani 1 1 d . . .
N1 N -0.02756(16) 0.3295(2) 0.40624(9) 0.0678(8) Uani 1 1 d . . .
C22 C 0.10869(13) 0.1886(2) 0.26686(8) 0.0412(6) Uani 1 1 d . . .
N2 N -0.06198(17) 0.3137(2) 0.44515(9) 0.0714(8) Uani 1 1 d . . .
F4 F 0.10251(14) -0.12608(17) 0.30805(7) 0.0984(8) Uani 1 1 d . . .
C24 C 0.05537(14) 0.0934(2) 0.33475(9) 0.0474(6) Uani 1 1 d . . .
H24 H 0.0450 0.0236 0.3521 0.057 Uiso 1 1 calc R . .
C25 C 0.09383(14) 0.0851(2) 0.29323(9) 0.0477(6) Uani 1 1 d . . .
F5 F 0.08827(18) -0.07307(19) 0.23747(8) 0.1140(9) Uani 1 1 d . . .
C26 C -0.02603(15) 0.1323(3) 0.42246(9) 0.0523(7) Uani 1 1 d . . .
H26 H -0.0175 0.0483 0.4209 0.063 Uiso 1 1 calc R . .
C27 C 0.17954(16) 0.1576(3) 0.15656(9) 0.0556(7) Uani 1 1 d . . .
H27 H 0.1786 0.1437 0.1245 0.067 Uiso 1 1 calc R . .
N8A N 0.12370(12) 0.1526(2) 0.18396(8) 0.0544(6) Uani 1 1 d . . .
N18 N 0.12046(19) 0.4184(2) 0.21383(10) 0.0831(9) Uani 1 1 d . . .
N7A N 0.22076(12) 0.2002(3) 0.22632(8) 0.0620(7) Uani 1 1 d . . .
F6 F 0.18742(14) -0.0450(2) 0.27065(11) 0.1231(11) Uani 1 1 d . . .
C31 C -0.06194(16) 0.1934(3) 0.45556(10) 0.0567(7) Uani 1 1 d . . .
H31 H -0.0834 0.1582 0.4815 0.068 Uiso 1 1 calc R . .
C32 C 0.23899(16) 0.1863(3) 0.18214(10) 0.0624(8) Uani 1 1 d . . .
H32 H 0.2852 0.1947 0.1704 0.075 Uiso 1 1 calc R . .
C7A C 0.0869(2) 0.5207(2) 0.27637(11) 0.0736(10) Uani 1 1 d . . .
H7A H 0.0704 0.5380 0.3062 0.088 Uiso 1 1 calc R . .
C34 C 0.1180(2) -0.0395(3) 0.27778(11) 0.0673(9) Uani 1 1 d . . .
C8A C 0.1038(2) 0.5980(3) 0.24396(13) 0.0853(12) Uani 1 1 d . . .
H8A H 0.1012 0.6829 0.2467 0.102 Uiso 1 1 calc R . .
N17 N 0.1261(2) 0.5369(3) 0.20521(13) 0.1000(11) 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
N8 N6A 1.328(3) . ?
N8 N5A 1.330(3) . ?
N8 C1A 1.427(3) . ?
C1A C7 1.381(3) . ?
C1A C2 1.389(3) . ?
N3A C4A 1.335(4) . ?
N3A N13 1.346(3) . ?
N3A C5 1.424(3) . ?
C1 C5 1.376(4) . ?
C1 C2 1.388(3) . ?
C2 N7 1.416(3) . ?
N13 N14 1.305(3) . ?
C4 C5 1.378(3) . ?
C4 C7 1.399(3) . ?
N7 C10 1.321(3) . ?
N7 N19A 1.328(3) . ?
F3 C13 1.328(4) . ?
N6A C11 1.323(3) . ?
F1 C13 1.322(3) . ?
C7 C13 1.505(4) . ?
N14 C3B 1.349(4) . ?
N5A C14 1.318(4) . ?
N19A N20A 1.337(4) . ?
C11 C14 1.370(4) . ?
C10 C9 1.293(4) . ?
C13 F2 1.321(4) . ?
C4A C3B 1.359(4) . ?
C9 N20A 1.388(5) . ?
N5 N7A 1.319(3) . ?
N5 N8A 1.323(3) . ?
N5 C22 1.430(3) . ?
N6 C26 1.343(3) . ?
N6 N1 1.345(3) . ?
N6 C19 1.426(3) . ?
N4 C7A 1.318(3) . ?
N4 N18 1.327(3) . ?
N4 C20 1.416(3) . ?
C2B C19 1.370(3) . ?
C2B C20 1.387(3) . ?
C19 C24 1.376(3) . ?
C20 C22 1.390(3) . ?
N1 N2 1.301(3) . ?
C22 C25 1.387(3) . ?
N2 C31 1.344(4) . ?
F4 C34 1.315(3) . ?
C24 C25 1.396(3) . ?
C25 C34 1.498(4) . ?
F5 C34 1.328(4) . ?
C26 C31 1.341(4) . ?
C27 N8A 1.308(3) . ?
C27 C32 1.358(4) . ?
N18 N17 1.320(4) . ?
N7A C32 1.322(4) . ?
F6 C34 1.310(4) . ?
C7A C8A 1.294(4) . ?
C8A N17 1.361(5) . ?

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
N6A N8 N5A 115.7(2) . . ?
N6A N8 C1A 123.0(2) . . ?
N5A N8 C1A 121.2(2) . . ?
C7 C1A C2 119.2(2) . . ?
C7 C1A N8 121.0(2) . . ?
C2 C1A N8 119.8(2) . . ?
C4A N3A N13 110.5(2) . . ?
C4A N3A C5 129.6(2) . . ?
N13 N3A C5 119.8(2) . . ?
C5 C1 C2 119.2(2) . . ?
C1 C2 C1A 120.5(2) . . ?
C1 C2 N7 117.1(2) . . ?
C1A C2 N7 122.4(2) . . ?
N14 N13 N3A 107.3(2) . . ?
C5 C4 C7 118.3(2) . . ?
C10 N7 N19A 115.4(2) . . ?
C10 N7 C2 120.5(2) . . ?
N19A N7 C2 124.0(2) . . ?
C1 C5 C4 121.8(2) . . ?
C1 C5 N3A 119.0(2) . . ?
C4 C5 N3A 119.2(2) . . ?
C11 N6A N8 102.5(2) . . ?
C1A C7 C4 121.0(2) . . ?
C1A C7 C13 121.9(2) . . ?
C4 C7 C13 117.2(2) . . ?
N13 N14 C3B 108.5(2) . . ?
C14 N5A N8 102.8(2) . . ?
N7 N19A N20A 103.0(3) . . ?
N6A C11 C14 109.5(2) . . ?
C9 C10 N7 103.9(3) . . ?
F2 C13 F1 107.7(3) . . ?
F2 C13 F3 105.8(2) . . ?
F1 C13 F3 105.9(3) . . ?
F2 C13 C7 112.4(3) . . ?
F1 C13 C7 112.2(2) . . ?
F3 C13 C7 112.4(3) . . ?
N5A C14 C11 109.4(2) . . ?
N3A C4A C3B 104.8(3) . . ?
C10 C9 N20A 110.0(3) . . ?
N14 C3B C4A 108.8(3) . . ?
N19A N20A C9 107.8(3) . . ?
N7A N5 N8A 115.0(2) . . ?
N7A N5 C22 121.4(2) . . ?
N8A N5 C22 123.5(2) . . ?
C26 N6 N1 109.8(2) . . ?
C26 N6 C19 130.5(2) . . ?
N1 N6 C19 119.7(2) . . ?
C7A N4 N18 112.9(2) . . ?
C7A N4 C20 121.9(2) . . ?
N18 N4 C20 125.2(2) . . ?
C19 C2B C20 119.4(2) . . ?
C2B C19 C24 121.9(2) . . ?
C2B C19 N6 118.9(2) . . ?
C24 C19 N6 119.2(2) . . ?
C2B C20 C22 120.4(2) . . ?
C2B C20 N4 117.4(2) . . ?
C22 C20 N4 122.2(2) . . ?
N2 N1 N6 107.3(2) . . ?
C25 C22 C20 118.9(2) . . ?
C25 C22 N5 119.6(2) . . ?
C20 C22 N5 121.5(2) . . ?
N1 N2 C31 108.6(2) . . ?
C19 C24 C25 118.2(2) . . ?
C22 C25 C24 121.1(2) . . ?
C22 C25 C34 121.0(2) . . ?
C24 C25 C34 117.9(2) . . ?
C31 C26 N6 105.2(3) . . ?
N8A C27 C32 109.4(2) . . ?
C27 N8A N5 103.4(2) . . ?
N17 N18 N4 104.7(3) . . ?
N5 N7A C32 103.0(2) . . ?
C26 C31 N2 109.1(3) . . ?
N7A C32 C27 109.2(2) . . ?
C8A C7A N4 104.7(3) . . ?
F6 C34 F4 107.0(3) . . ?
F6 C34 F5 104.8(3) . . ?
F4 C34 F5 106.5(3) . . ?
F6 C34 C25 112.7(3) . . ?
F4 C34 C25 112.8(2) . . ?
F5 C34 C25 112.5(3) . . ?
C7A C8A N17 110.1(3) . . ?
N18 N17 C8A 107.5(3) . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        26.05
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.529
_refine_diff_density_min         -0.488
_refine_diff_density_rms         0.063
_database_code_depnum_ccdc_archive 'CCDC 949068'
#######################################################################
#
#                 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_rt
_audit_creation_date             2012-07-28
_audit_creation_method           
;
  Olex2 1.1
  (compiled 2011.11.01 svn.r2039, GUI svn.r3906)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C13 H8 F3 N9'
_chemical_formula_sum            'C9 H12 F3 N8'
_chemical_formula_weight         289.27
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C9 H12 F3 N8'
_chemical_oxdiff_usercomment     Sudheer
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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x, -y-1/2, z-1/2'

_cell_length_a                   13.2240(8)
_cell_length_b                   10.7927(7)
_cell_length_c                   20.8619(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 93.504(5)
_cell_angle_gamma                90.00
_cell_volume                     2971.9(3)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    2064
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.2940
_cell_measurement_theta_min      2.7128
_exptl_absorpt_coefficient_mu    0.114
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.91134
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.293
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       ?
_exptl_crystal_F_000             1192
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0300
_diffrn_reflns_av_unetI/netI     0.0413
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            9721
_diffrn_reflns_theta_full        23.26
_diffrn_reflns_theta_max         23.26
_diffrn_reflns_theta_min         2.72
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 16.3291
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -50.00   62.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -       18.7003  -19.0000  -60.0000 112

#__ type_ start__ end____ width___ exp.time_
  2 omega  -29.00   38.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -       18.7003  -57.0000   60.0000 67

#__ type_ start__ end____ width___ exp.time_
  3 omega  -11.00   21.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      -18.8566  -99.0000  -90.0000 32

#__ type_ start__ end____ width___ exp.time_
  4 omega  -17.00    9.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      -18.8566  -99.0000   90.0000 26
;
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0406622000
_diffrn_orient_matrix_UB_12      0.0428881000
_diffrn_orient_matrix_UB_13      0.0031737000
_diffrn_orient_matrix_UB_21      -0.0349923000
_diffrn_orient_matrix_UB_22      0.0489733000
_diffrn_orient_matrix_UB_23      0.0034404000
_diffrn_orient_matrix_UB_31      0.0030788000
_diffrn_orient_matrix_UB_32      -0.0089879000
_diffrn_orient_matrix_UB_33      0.0337460000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                2874
_reflns_number_total             4251
_reflns_odcompleteness_completeness 99.77
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     25.30
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
XL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_refine_diff_density_max         0.341
_refine_diff_density_min         -0.234
_refine_diff_density_rms         0.040
_refine_ls_extinction_coef       0.0005(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.814
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     452
_refine_ls_number_reflns         4251
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0892
_refine_ls_R_factor_gt           0.0571
_refine_ls_restrained_S_all      0.814
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1414P)²+2.9492P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1654
_refine_ls_wR_factor_ref         0.2066
_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. 
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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
C12 C 0.3622(5) 1.0430(5) 0.1433(3) 0.1039(19) Uani 1 1 d . . .
H12 H 0.4075 1.0782 0.1162 0.125 Uiso 1 1 calc R . .
C11 C 0.2919(5) 1.1032(5) 0.1724(3) 0.1080(19) Uani 1 1 d . . .
H11 H 0.2797 1.1879 0.1692 0.130 Uiso 1 1 calc R . .
N4 N 0.3836(2) 0.6815(3) 0.18441(12) 0.0475(8) Uani 1 1 d . . .
N13 N -0.3507(2) 1.1931(3) 0.56251(12) 0.0474(8) Uani 1 1 d . . .
N10 N -0.0400(2) 1.2328(3) 0.39266(15) 0.0526(8) Uani 1 1 d . . .
C19 C -0.2694(3) 1.2026(3) 0.52089(15) 0.0452(9) Uani 1 1 d . . .
N1 N 0.0545(2) 0.7320(3) 0.33824(16) 0.0598(9) Uani 1 1 d . . .
N17 N -0.2827(2) 1.4285(3) 0.52097(15) 0.0583(8) Uani 1 1 d . . .
C21 C -0.1622(3) 1.3272(4) 0.45809(18) 0.0537(10) Uani 1 1 d . . .
H21 H -0.1417 1.4047 0.4444 0.064 Uiso 1 1 calc R . .
C18 C -0.2194(3) 1.0975(3) 0.50123(16) 0.0469(9) Uani 1 1 d . . .
C20 C -0.2389(3) 1.3170(3) 0.49950(17) 0.0480(9) Uani 1 1 d . . .
C17 C -0.1434(3) 1.1064(4) 0.45900(17) 0.0499(9) Uani 1 1 d . . .
H17 H -0.1108 1.0356 0.4454 0.060 Uiso 1 1 calc R . .
C7 C 0.2481(3) 0.8086(3) 0.22554(17) 0.0507(9) Uani 1 1 d . . .
C5 C 0.2533(3) 0.5904(3) 0.24636(18) 0.0525(9) Uani 1 1 d . . .
C16 C -0.1163(2) 1.2217(4) 0.43724(16) 0.0477(9) Uani 1 1 d . . .
C8 C 0.1670(3) 0.8198(4) 0.26380(18) 0.0537(10) Uani 1 1 d . . .
H8 H 0.1365 0.8965 0.2689 0.064 Uiso 1 1 calc R . .
F6 F -0.1758(2) 0.8884(2) 0.51339(15) 0.1067(11) Uani 1 1 d . . .
N8 N 0.2837(2) 0.9183(3) 0.19713(15) 0.0583(8) Uani 1 1 d . . .
N11 N -0.0042(3) 1.3457(4) 0.3783(2) 0.0829(12) Uani 1 1 d . . .
C6 C 0.2943(3) 0.6943(3) 0.21797(16) 0.0468(9) Uani 1 1 d . . .
F5 F -0.2524(2) 0.9673(3) 0.58805(13) 0.0998(10) Uani 1 1 d . . .
F4 F -0.3330(2) 0.9312(3) 0.50054(16) 0.1056(10) Uani 1 1 d . . .
C3 C 0.1318(3) 0.7180(3) 0.29401(18) 0.0518(9) Uani 1 1 d . . .
F1 F 0.2539(2) 0.3784(3) 0.26973(18) 0.1269(14) Uani 1 1 d . . .
N2 N 0.0181(4) 0.8448(4) 0.3497(2) 0.1012(15) Uani 1 1 d . . .
C14 C -0.4456(3) 1.1564(4) 0.54879(16) 0.0530(10) Uani 1 1 d . . .
H14 H -0.4738 1.1276 0.5096 0.064 Uiso 1 1 calc R . .
C4 C 0.1726(3) 0.6017(4) 0.28453(18) 0.0562(10) Uani 1 1 d . . .
H4 H 0.1457 0.5323 0.3037 0.067 Uiso 1 1 calc R . .
F2 F 0.2929(3) 0.4304(3) 0.17679(18) 0.1312(14) Uani 1 1 d . . .
F3 F 0.3938(2) 0.4576(3) 0.2552(2) 0.1427(16) Uani 1 1 d . . .
N9 N 0.3811(3) 0.6579(3) 0.12091(15) 0.0701(10) Uani 1 1 d . . .
N16 N -0.2255(3) 1.5253(4) 0.5359(2) 0.0920(13) Uani 1 1 d . . .
N12 N 0.0629(3) 1.3313(4) 0.3365(2) 0.0853(12) Uani 1 1 d . . .
N3 N -0.0456(3) 0.8327(4) 0.3943(2) 0.1000(15) Uani 1 1 d . . .
N5 N 0.4746(3) 0.6548(4) 0.10521(16) 0.0773(11) Uani 1 1 d . . .
C15 C 0.0049(3) 1.1472(4) 0.3575(2) 0.0700(12) Uani 1 1 d . . .
H15 H -0.0071 1.0623 0.3568 0.084 Uiso 1 1 calc R . .
C26 C -0.2452(3) 0.9715(4) 0.5249(2) 0.0647(11) Uani 1 1 d . . .
C2 C 0.0143(4) 0.6505(5) 0.3775(3) 0.0884(16) Uani 1 1 d . . .
H2 H 0.0279 0.5660 0.3803 0.106 Uiso 1 1 calc R . .
N6 N 0.3582(4) 0.9246(4) 0.1587(3) 0.1184(18) Uani 1 1 d . . .
N19 N -0.3382(3) 1.2301(4) 0.62398(15) 0.0808(12) Uani 1 1 d . . .
N18 N -0.3804(3) 1.4455(4) 0.5268(2) 0.0787(11) Uani 1 1 d . . .
C1 C 0.5356(3) 0.6750(5) 0.1569(2) 0.0737(13) Uani 1 1 d . . .
H1 H 0.6060 0.6767 0.1579 0.088 Uiso 1 1 calc R . .
N7 N 0.2412(4) 1.0251(4) 0.2067(3) 0.1200(19) Uani 1 1 d . . .
C9 C -0.4918(3) 1.1699(4) 0.60375(19) 0.0648(11) Uani 1 1 d . . .
H9 H -0.5593 1.1514 0.6097 0.078 Uiso 1 1 calc R . .
C25 C -0.3861(4) 1.5610(4) 0.5472(2) 0.0813(14) Uani 1 1 d . . .
H25 H -0.4454 1.6021 0.5563 0.098 Uiso 1 1 calc R . .
C13 C 0.2974(4) 0.4656(4) 0.2383(3) 0.0777(14) Uani 1 1 d . . .
C10 C 0.0705(3) 1.2097(5) 0.3235(2) 0.0722(12) Uani 1 1 d . . .
H10 H 0.1144 1.1747 0.2954 0.087 Uiso 1 1 calc R . .
C1A C -0.0494(4) 0.7149(5) 0.4119(3) 0.0877(15) Uani 1 1 d . . .
H1A H -0.0897 0.6826 0.4428 0.105 Uiso 1 1 calc R . .
C1B C 0.4796(3) 0.6926(4) 0.20742(17) 0.0659(12) Uani 1 1 d . . .
H1B H 0.5026 0.7091 0.2496 0.079 Uiso 1 1 calc R . .
N20 N -0.4254(3) 1.2141(4) 0.64827(16) 0.0897(13) Uani 1 1 d . . .
C24 C -0.2918(4) 1.6100(5) 0.5529(3) 0.0948(17) Uani 1 1 d . . .
H24 H -0.2759 1.6901 0.5666 0.114 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
C12 C11 1.313(7) . ?
C12 N6 1.319(7) . ?
C11 N7 1.315(6) . ?
N4 C6 1.416(4) . ?
N4 N9 1.347(4) . ?
N4 C1B 1.334(5) . ?
N13 C19 1.427(4) . ?
N13 C14 1.331(5) . ?
N13 N19 1.344(4) . ?
N10 C16 1.419(4) . ?
N10 N11 1.347(5) . ?
N10 C15 1.341(5) . ?
C19 C18 1.387(5) . ?
C19 C20 1.381(5) . ?
N1 C3 1.427(4) . ?
N1 N2 1.335(5) . ?
N1 C2 1.334(6) . ?
N17 C20 1.420(5) . ?
N17 N16 1.315(5) . ?
N17 N18 1.318(4) . ?
C21 C20 1.376(5) . ?
C21 C16 1.373(5) . ?
C18 C17 1.380(5) . ?
C18 C26 1.494(6) . ?
C17 C16 1.379(5) . ?
C7 C8 1.380(5) . ?
C7 N8 1.418(5) . ?
C7 C6 1.391(5) . ?
C5 C6 1.393(5) . ?
C5 C4 1.376(5) . ?
C5 C13 1.482(6) . ?
C8 C3 1.363(5) . ?
F6 C26 1.315(5) . ?
N8 N6 1.311(5) . ?
N8 N7 1.302(5) . ?
N11 N12 1.292(5) . ?
F5 C26 1.328(5) . ?
F4 C26 1.312(5) . ?
C3 C4 1.385(5) . ?
F1 C13 1.301(5) . ?
N2 N3 1.300(5) . ?
C14 C9 1.340(5) . ?
F2 C13 1.336(6) . ?
F3 C13 1.306(6) . ?
N9 N5 1.298(5) . ?
N16 C24 1.330(6) . ?
N12 C10 1.345(6) . ?
N3 C1A 1.325(6) . ?
N5 C1 1.325(5) . ?
C15 C10 1.336(6) . ?
C2 C1A 1.334(6) . ?
N19 N20 1.299(5) . ?
N18 C25 1.321(6) . ?
C1 C1B 1.339(5) . ?
C9 N20 1.328(5) . ?
C25 C24 1.352(6) . ?

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
C11 C12 N6 109.1(5) . . ?
C12 C11 N7 109.4(5) . . ?
N9 N4 C6 122.2(3) . . ?
C1B N4 C6 128.1(3) . . ?
C1B N4 N9 109.7(3) . . ?
C14 N13 C19 128.8(3) . . ?
C14 N13 N19 110.7(3) . . ?
N19 N13 C19 120.4(3) . . ?
N11 N10 C16 119.7(3) . . ?
C15 N10 C16 131.0(3) . . ?
C15 N10 N11 109.2(3) . . ?
C18 C19 N13 120.7(3) . . ?
C20 C19 N13 120.5(3) . . ?
C20 C19 C18 118.8(3) . . ?
N2 N1 C3 119.5(3) . . ?
C2 N1 C3 130.9(4) . . ?
C2 N1 N2 109.3(3) . . ?
N16 N17 C20 120.5(3) . . ?
N16 N17 N18 114.9(3) . . ?
N18 N17 C20 124.6(3) . . ?
C16 C21 C20 119.3(3) . . ?
C19 C18 C26 121.6(3) . . ?
C17 C18 C19 120.7(3) . . ?
C17 C18 C26 117.7(3) . . ?
C19 C20 N17 121.6(3) . . ?
C21 C20 C19 121.0(3) . . ?
C21 C20 N17 117.4(3) . . ?
C16 C17 C18 119.1(3) . . ?
C8 C7 N8 117.3(3) . . ?
C8 C7 C6 120.4(3) . . ?
C6 C7 N8 122.3(3) . . ?
C6 C5 C13 121.1(3) . . ?
C4 C5 C6 120.7(3) . . ?
C4 C5 C13 118.1(3) . . ?
C21 C16 N10 118.9(3) . . ?
C21 C16 C17 121.0(3) . . ?
C17 C16 N10 120.1(3) . . ?
C3 C8 C7 119.7(3) . . ?
N6 N8 C7 125.5(3) . . ?
N7 N8 C7 121.2(3) . . ?
N7 N8 N6 113.3(4) . . ?
N12 N11 N10 107.8(3) . . ?
C7 C6 N4 121.9(3) . . ?
C7 C6 C5 118.7(3) . . ?
C5 C6 N4 119.4(3) . . ?
C8 C3 N1 119.5(3) . . ?
C8 C3 C4 121.2(3) . . ?
C4 C3 N1 119.3(3) . . ?
N3 N2 N1 107.0(4) . . ?
N13 C14 C9 104.9(3) . . ?
C5 C4 C3 119.0(4) . . ?
N5 N9 N4 106.6(3) . . ?
N17 N16 C24 103.3(4) . . ?
N11 N12 C10 108.5(4) . . ?
N2 N3 C1A 109.4(4) . . ?
N9 N5 C1 109.4(3) . . ?
C10 C15 N10 105.4(4) . . ?
F6 C26 C18 112.6(3) . . ?
F6 C26 F5 104.5(3) . . ?
F5 C26 C18 113.0(4) . . ?
F4 C26 C18 112.8(3) . . ?
F4 C26 F6 108.3(4) . . ?
F4 C26 F5 104.9(3) . . ?
N1 C2 C1A 105.9(5) . . ?
N8 N6 C12 103.9(4) . . ?
N20 N19 N13 105.8(3) . . ?
N17 N18 C25 103.7(4) . . ?
N5 C1 C1B 109.0(4) . . ?
N8 N7 C11 104.2(4) . . ?
N20 C9 C14 108.7(4) . . ?
N18 C25 C24 109.1(4) . . ?
F1 C13 C5 114.3(3) . . ?
F1 C13 F2 106.5(4) . . ?
F1 C13 F3 105.7(5) . . ?
F2 C13 C5 111.9(4) . . ?
F3 C13 C5 114.4(4) . . ?
F3 C13 F2 103.1(4) . . ?
C15 C10 N12 109.1(4) . . ?
N3 C1A C2 108.4(5) . . ?
N4 C1B C1 105.3(3) . . ?
N19 N20 C9 109.9(3) . . ?
N16 C24 C25 109.1(4) . . ?

_database_code_depnum_ccdc_archive 'CCDC 949069'
