# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_150513a
_database_code_depnum_ccdc_archive 'CCDC 1412525'
_audit_update_record             
;
2015-07-13 deposited with the CCDC.
2015-09-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C40 H28 F12 N16 O4'
_chemical_formula_weight         1024.78

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   Pnma

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

_cell_length_a                   11.427(7)
_cell_length_b                   6.760(4)
_cell_length_c                   14.006(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1081.9(12)
_cell_formula_units_Z            1
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      none
_exptl_crystal_density_diffrn    1.573
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             520
_exptl_absorpt_coefficient_mu    0.142
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9613
_exptl_absorpt_correction_T_max  0.9721
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5767
_diffrn_reflns_av_R_equivalents  0.0224
_diffrn_reflns_av_sigmaI/netI    0.0272
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.30
_diffrn_reflns_theta_max         26.00
_reflns_number_total             1155
_reflns_number_gt                1007
_reflns_threshold_expression     >2sigma(I)

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

_refine_special_details          
; 
 Refinement of 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)+(0.0796P)²+1.1566P] 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       0.009(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         1155
_refine_ls_number_parameters     109
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0681
_refine_ls_R_factor_gt           0.0617
_refine_ls_wR_factor_ref         0.1830
_refine_ls_wR_factor_gt          0.1759
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_restrained_S_all      1.076
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.6223(3) 0.7500 0.7411(2) 0.0755(10) Uani 1 2 d S . .
N1 N 0.4409(3) 0.7500 0.2654(2) 0.0447(8) Uani 1 2 d S . .
N2 N 0.3684(2) 0.7500 0.3389(2) 0.0429(7) Uani 1 2 d S . .
N3 N 0.2577(3) 0.7500 0.3138(3) 0.0851(15) Uani 1 2 d S . .
N4 N 0.2565(3) 0.7500 0.2201(3) 0.0855(15) Uani 1 2 d S . .
C1 C 0.4028(3) 0.7500 0.0922(3) 0.0554(10) Uani 1 2 d S . .
C2 C 0.3673(3) 0.7500 0.1939(3) 0.0467(9) Uani 1 2 d S . .
C3 C 0.4060(3) 0.7500 0.4364(2) 0.0380(8) Uani 1 2 d S . .
C4 C 0.5244(3) 0.7500 0.4561(2) 0.0396(8) Uani 1 2 d S . .
H4 H 0.5795 0.7500 0.4072 0.048 Uiso 1 2 calc SR . .
C5 C 0.5585(3) 0.7500 0.5503(2) 0.0409(8) Uani 1 2 d S . .
H5 H 0.6378 0.7500 0.5652 0.049 Uiso 1 2 calc SR . .
C6 C 0.4764(3) 0.7500 0.6237(2) 0.0404(8) Uani 1 2 d S . .
C7 C 0.3582(3) 0.7500 0.6009(3) 0.0453(9) Uani 1 2 d S . .
H7 H 0.3026 0.7500 0.6494 0.054 Uiso 1 2 calc SR . .
C8 C 0.3230(3) 0.7500 0.5072(3) 0.0449(8) Uani 1 2 d S . .
H8 H 0.2438 0.7500 0.4919 0.054 Uiso 1 2 calc SR . .
C9 C 0.5189(3) 0.7500 0.7245(3) 0.0486(9) Uani 1 2 d S . .
C10 C 0.4318(4) 0.7500 0.8036(3) 0.0732(14) Uani 1 2 d S . .
H10A H 0.4715 0.7674 0.8635 0.110 Uiso 0.50 1 calc PR . .
H10B H 0.3905 0.6263 0.8041 0.110 Uiso 0.50 1 calc PR . .
H10C H 0.3772 0.8563 0.7944 0.110 Uiso 0.50 1 calc PR . .
F1 F 0.5126(3) 0.7500 0.0802(2) 0.1263(18) Uani 1 2 d S . .
F2 F 0.3619(3) 0.8990(5) 0.04690(18) 0.1579(16) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0543(18) 0.117(3) 0.0552(17) 0.000 -0.0103(14) 0.000
N1 0.0388(15) 0.0563(18) 0.0391(16) 0.000 0.0017(12) 0.000
N2 0.0337(14) 0.0516(17) 0.0434(15) 0.000 0.0021(11) 0.000
N3 0.0363(17) 0.169(5) 0.050(2) 0.000 0.0004(15) 0.000
N4 0.0420(19) 0.167(5) 0.0481(19) 0.000 -0.0039(15) 0.000
C1 0.048(2) 0.076(3) 0.043(2) 0.000 -0.0082(16) 0.000
C2 0.0414(18) 0.054(2) 0.0444(19) 0.000 -0.0031(15) 0.000
C3 0.0378(16) 0.0376(17) 0.0386(17) 0.000 0.0012(13) 0.000
C4 0.0351(16) 0.0404(17) 0.0433(17) 0.000 0.0065(13) 0.000
C5 0.0354(16) 0.0406(18) 0.0465(18) 0.000 -0.0010(14) 0.000
C6 0.0428(17) 0.0371(16) 0.0414(17) 0.000 0.0032(14) 0.000
C7 0.0399(18) 0.050(2) 0.0457(19) 0.000 0.0102(14) 0.000
C8 0.0308(15) 0.055(2) 0.0491(19) 0.000 0.0021(14) 0.000
C9 0.052(2) 0.048(2) 0.046(2) 0.000 -0.0011(16) 0.000
C10 0.072(3) 0.106(4) 0.041(2) 0.000 0.0033(19) 0.000
F1 0.0585(17) 0.265(6) 0.0552(16) 0.000 0.0105(13) 0.000
F2 0.216(3) 0.183(3) 0.0741(15) 0.0550(17) 0.0381(17) 0.110(3)

_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C9 1.204(5) . ?
N1 C2 1.307(5) . ?
N1 N2 1.322(4) . ?
N2 N3 1.312(4) . ?
N2 C3 1.431(4) . ?
N3 N4 1.313(5) . ?
N4 C2 1.319(5) . ?
C1 F1 1.266(5) . ?
C1 F2 1.279(3) 8_575 ?
C1 F2 1.279(3) . ?
C1 C2 1.481(5) . ?
C3 C8 1.372(5) . ?
C3 C4 1.382(5) . ?
C4 C5 1.375(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.391(5) . ?
C5 H5 0.9300 . ?
C6 C7 1.388(5) . ?
C6 C9 1.494(5) . ?
C7 C8 1.373(5) . ?
C7 H7 0.9300 . ?
C8 H8 0.9300 . ?
C9 C10 1.489(6) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 N1 N2 101.2(3) . . ?
N3 N2 N1 113.3(3) . . ?
N3 N2 C3 123.0(3) . . ?
N1 N2 C3 123.7(3) . . ?
N2 N3 N4 106.2(3) . . ?
N3 N4 C2 105.5(3) . . ?
F1 C1 F2 107.2(3) . 8_575 ?
F1 C1 F2 107.2(3) . . ?
F2 C1 F2 104.0(5) 8_575 . ?
F1 C1 C2 113.5(3) . . ?
F2 C1 C2 112.2(3) 8_575 . ?
F2 C1 C2 112.2(3) . . ?
N1 C2 N4 113.9(3) . . ?
N1 C2 C1 124.1(3) . . ?
N4 C2 C1 122.0(3) . . ?
C8 C3 C4 122.2(3) . . ?
C8 C3 N2 118.8(3) . . ?
C4 C3 N2 119.0(3) . . ?
C5 C4 C3 118.0(3) . . ?
C5 C4 H4 121.0 . . ?
C3 C4 H4 121.0 . . ?
C4 C5 C6 121.2(3) . . ?
C4 C5 H5 119.4 . . ?
C6 C5 H5 119.4 . . ?
C7 C6 C5 119.1(3) . . ?
C7 C6 C9 122.3(3) . . ?
C5 C6 C9 118.6(3) . . ?
C8 C7 C6 120.3(3) . . ?
C8 C7 H7 119.8 . . ?
C6 C7 H7 119.8 . . ?
C3 C8 C7 119.2(3) . . ?
C3 C8 H8 120.4 . . ?
C7 C8 H8 120.4 . . ?
O1 C9 C10 120.9(4) . . ?
O1 C9 C6 120.1(3) . . ?
C10 C9 C6 119.1(3) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C2 N1 N2 N3 0.0 . . . . ?
C2 N1 N2 C3 180.0 . . . . ?
N1 N2 N3 N4 0.0 . . . . ?
C3 N2 N3 N4 180.0 . . . . ?
N2 N3 N4 C2 0.0 . . . . ?
N2 N1 C2 N4 0.0 . . . . ?
N2 N1 C2 C1 180.0 . . . . ?
N3 N4 C2 N1 0.0 . . . . ?
N3 N4 C2 C1 180.0 . . . . ?
F1 C1 C2 N1 0.0 . . . . ?
F2 C1 C2 N1 121.7(3) 8_575 . . . ?
F2 C1 C2 N1 -121.7(3) . . . . ?
F1 C1 C2 N4 180.0 . . . . ?
F2 C1 C2 N4 -58.3(3) 8_575 . . . ?
F2 C1 C2 N4 58.3(3) . . . . ?
N3 N2 C3 C8 0.0 . . . . ?
N1 N2 C3 C8 180.0 . . . . ?
N3 N2 C3 C4 180.0 . . . . ?
N1 N2 C3 C4 0.0 . . . . ?
C8 C3 C4 C5 0.0 . . . . ?
N2 C3 C4 C5 180.0 . . . . ?
C3 C4 C5 C6 0.0 . . . . ?
C4 C5 C6 C7 0.0 . . . . ?
C4 C5 C6 C9 180.0 . . . . ?
C5 C6 C7 C8 0.0 . . . . ?
C9 C6 C7 C8 180.0 . . . . ?
C4 C3 C8 C7 0.0 . . . . ?
N2 C3 C8 C7 180.0 . . . . ?
C6 C7 C8 C3 0.0 . . . . ?
C7 C6 C9 O1 180.0 . . . . ?
C5 C6 C9 O1 0.000(1) . . . . ?
C7 C6 C9 C10 0.000(1) . . . . ?
C5 C6 C9 C10 180.000(1) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.663
_refine_diff_density_min         -0.408
_refine_diff_density_rms         0.051

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_150630a
_database_code_depnum_ccdc_archive 'CCDC 1412621'
_audit_update_record             
;
2015-07-13 deposited with the CCDC.
2015-09-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C8 H5 F3 N4 O'
_chemical_formula_weight         230.16

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   Pnma

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

_cell_length_a                   9.5762(8)
_cell_length_b                   7.0422(6)
_cell_length_c                   14.1082(11)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     951.42(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1847
_cell_measurement_theta_min      2.57
_cell_measurement_theta_max      23.81

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            COLORLESS
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      NONE
_exptl_crystal_density_diffrn    1.607
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             464
_exptl_absorpt_coefficient_mu    0.152
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.9588
_exptl_absorpt_correction_T_max  0.9703
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5083
_diffrn_reflns_av_R_equivalents  0.0175
_diffrn_reflns_av_sigmaI/netI    0.0129
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.57
_diffrn_reflns_theta_max         25.99
_reflns_number_total             1017
_reflns_number_gt                828
_reflns_threshold_expression     >2sigma(I)

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

_refine_special_details          
; 
 Refinement of 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)+(0.1183P)²+0.8502P] 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       NONE
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         1017
_refine_ls_number_parameters     96
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0839
_refine_ls_R_factor_gt           0.0745
_refine_ls_wR_factor_ref         0.2392
_refine_ls_wR_factor_gt          0.2266
_refine_ls_goodness_of_fit_ref   1.093
_refine_ls_restrained_S_all      1.093
_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 0.5409(3) 0.1047(5) 0.1703(2) 0.1402(14) Uani 1 1 d . . .
F2 F 0.3851(5) 0.2500 0.2436(3) 0.263(5) Uani 1 2 d S . .
O1 O -0.3503(3) 0.2500 -0.1347(3) 0.0869(13) Uani 1 2 d S . .
H1 H -0.4026 0.2997 -0.0959 0.130 Uiso 0.50 1 calc PR . .
N1 N 0.1945(3) 0.2500 -0.0039(2) 0.0531(9) Uani 1 2 d S . .
N2 N 0.2264(4) 0.2500 0.0875(2) 0.0619(10) Uani 1 2 d S . .
N3 N 0.4145(4) 0.2500 -0.0039(3) 0.0795(14) Uani 1 2 d S . .
N4 N 0.3044(4) 0.2500 -0.0606(3) 0.0733(13) Uani 1 2 d S . .
C1 C 0.0270(5) 0.2500 -0.1335(3) 0.0621(12) Uani 1 2 d S . .
H1A H 0.1000 0.2500 -0.1770 0.075 Uiso 1 2 calc SR . .
C2 C -0.1099(5) 0.2500 -0.1640(3) 0.0683(14) Uani 1 2 d S . .
H2 H -0.1290 0.2500 -0.2286 0.082 Uiso 1 2 calc SR . .
C3 C -0.2178(4) 0.2500 -0.1004(3) 0.0591(11) Uani 1 2 d S . .
C4 C -0.1896(4) 0.2500 -0.0043(3) 0.0637(13) Uani 1 2 d S . .
H4 H -0.2627 0.2500 0.0391 0.076 Uiso 1 2 calc SR . .
C5 C -0.0528(4) 0.2500 0.0276(3) 0.0600(12) Uani 1 2 d S . .
H5 H -0.0334 0.2500 0.0922 0.072 Uiso 1 2 calc SR . .
C6 C 0.0537(4) 0.2500 -0.0374(3) 0.0487(10) Uani 1 2 d S . .
C7 C 0.3630(5) 0.2500 0.0846(3) 0.0671(13) Uani 1 2 d S . .
C8 C 0.4522(6) 0.2500 0.1696(4) 0.0879(18) Uani 1 2 d S . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
F1 0.144(3) 0.130(3) 0.147(3) 0.022(2) -0.079(2) 0.009(2)
F2 0.094(3) 0.647(17) 0.049(2) 0.000 -0.015(2) 0.000
O1 0.0520(19) 0.137(4) 0.071(2) 0.000 -0.0061(16) 0.000
N1 0.0492(18) 0.065(2) 0.0452(18) 0.000 0.0017(14) 0.000
N2 0.059(2) 0.080(3) 0.0463(19) 0.000 -0.0020(16) 0.000
N3 0.048(2) 0.129(4) 0.062(2) 0.000 -0.0013(18) 0.000
N4 0.046(2) 0.120(4) 0.054(2) 0.000 0.0045(16) 0.000
C1 0.054(2) 0.088(3) 0.045(2) 0.000 0.0067(18) 0.000
C2 0.060(3) 0.100(4) 0.045(2) 0.000 -0.0017(19) 0.000
C3 0.046(2) 0.071(3) 0.060(3) 0.000 -0.0008(18) 0.000
C4 0.050(2) 0.083(3) 0.057(3) 0.000 0.0119(19) 0.000
C5 0.057(2) 0.076(3) 0.047(2) 0.000 0.0054(18) 0.000
C6 0.048(2) 0.051(2) 0.047(2) 0.000 0.0033(16) 0.000
C7 0.058(3) 0.084(3) 0.059(3) 0.000 -0.004(2) 0.000
C8 0.070(3) 0.124(5) 0.070(3) 0.000 -0.014(3) 0.000

_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C8 1.330(5) . ?
F2 C8 1.225(7) . ?
O1 C3 1.358(5) . ?
O1 H1 0.8200 . ?
N1 N4 1.323(5) . ?
N1 N2 1.325(5) . ?
N1 C6 1.429(5) . ?
N2 C7 1.309(6) . ?
N3 N4 1.323(5) . ?
N3 C7 1.342(6) . ?
C1 C2 1.379(6) . ?
C1 C6 1.380(6) . ?
C1 H1A 0.9300 . ?
C2 C3 1.369(6) . ?
C2 H2 0.9300 . ?
C3 C4 1.383(6) . ?
C4 C5 1.385(6) . ?
C4 H4 0.9300 . ?
C5 C6 1.371(5) . ?
C5 H5 0.9300 . ?
C7 C8 1.473(7) . ?
C8 F1 1.330(5) 8_565 ?

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
C3 O1 H1 109.5 . . ?
N4 N1 N2 113.9(3) . . ?
N4 N1 C6 123.4(3) . . ?
N2 N1 C6 122.6(3) . . ?
C7 N2 N1 101.5(4) . . ?
N4 N3 C7 105.6(4) . . ?
N1 N4 N3 105.5(4) . . ?
C2 C1 C6 118.9(4) . . ?
C2 C1 H1A 120.6 . . ?
C6 C1 H1A 120.6 . . ?
C3 C2 C1 120.8(4) . . ?
C3 C2 H2 119.6 . . ?
C1 C2 H2 119.6 . . ?
O1 C3 C2 118.1(4) . . ?
O1 C3 C4 122.1(4) . . ?
C2 C3 C4 119.7(4) . . ?
C3 C4 C5 120.2(4) . . ?
C3 C4 H4 119.9 . . ?
C5 C4 H4 119.9 . . ?
C6 C5 C4 119.1(4) . . ?
C6 C5 H5 120.5 . . ?
C4 C5 H5 120.5 . . ?
C5 C6 C1 121.3(4) . . ?
C5 C6 N1 118.7(4) . . ?
C1 C6 N1 120.0(4) . . ?
N2 C7 N3 113.4(4) . . ?
N2 C7 C8 123.6(5) . . ?
N3 C7 C8 123.0(5) . . ?
F2 C8 F1 109.2(4) . 8_565 ?
F2 C8 F1 109.2(4) . . ?
F1 C8 F1 100.5(5) 8_565 . ?
F2 C8 C7 113.0(5) . . ?
F1 C8 C7 112.1(3) 8_565 . ?
F1 C8 C7 112.1(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N4 N1 N2 C7 0.0 . . . . ?
C6 N1 N2 C7 180.0 . . . . ?
N2 N1 N4 N3 0.0 . . . . ?
C6 N1 N4 N3 180.0 . . . . ?
C7 N3 N4 N1 0.0 . . . . ?
C6 C1 C2 C3 0.0 . . . . ?
C1 C2 C3 O1 180.0 . . . . ?
C1 C2 C3 C4 0.0 . . . . ?
O1 C3 C4 C5 180.0 . . . . ?
C2 C3 C4 C5 0.0 . . . . ?
C3 C4 C5 C6 0.0 . . . . ?
C4 C5 C6 C1 0.0 . . . . ?
C4 C5 C6 N1 180.0 . . . . ?
C2 C1 C6 C5 0.0 . . . . ?
C2 C1 C6 N1 180.0 . . . . ?
N4 N1 C6 C5 180.0 . . . . ?
N2 N1 C6 C5 0.0 . . . . ?
N4 N1 C6 C1 0.0 . . . . ?
N2 N1 C6 C1 180.0 . . . . ?
N1 N2 C7 N3 0.0 . . . . ?
N1 N2 C7 C8 180.0 . . . . ?
N4 N3 C7 N2 0.0 . . . . ?
N4 N3 C7 C8 180.0 . . . . ?
N2 C7 C8 F2 0.0 . . . . ?
N3 C7 C8 F2 180.0 . . . . ?
N2 C7 C8 F1 -123.9(4) . . . 8_565 ?
N3 C7 C8 F1 56.1(4) . . . 8_565 ?
N2 C7 C8 F1 123.9(4) . . . . ?
N3 C7 C8 F1 -56.1(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.99
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.510
_refine_diff_density_min         -0.423
_refine_diff_density_rms         0.058


