# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_wh20180529
_database_code_depnum_ccdc_archive 'CCDC 1853088'
_audit_update_record             
;
2018-07-03 deposited with the CCDC.
2018-08-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         C11H6F7N2
_chemical_formula_sum            'C11 H6 F7 N2'
_chemical_formula_weight         299.18

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           orthorhombic
_symmetry_space_group_name_H-M   Pbca

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

_cell_length_a                   9.1202(10)
_cell_length_b                   8.3186(10)
_cell_length_c                   33.169(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2516.4(7)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3284
_cell_measurement_theta_min      4.1160
_cell_measurement_theta_max      23.0690

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.579
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1192
_exptl_absorpt_coefficient_mu    0.168
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9735
_exptl_absorpt_correction_T_max  0.9801
_exptl_absorpt_process_details   sadabs

_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  'four-circle diffractometer'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12264
_diffrn_reflns_av_R_equivalents  0.0711
_diffrn_reflns_av_sigmaI/netI    0.0389
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -40
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_theta_min         3.37
_diffrn_reflns_theta_max         25.50
_reflns_number_total             2319
_reflns_number_gt                1650
_reflns_threshold_expression     >2sigma(I)

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

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.2000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2319
_refine_ls_number_parameters     181
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1468
_refine_ls_R_factor_gt           0.1311
_refine_ls_wR_factor_ref         0.4000
_refine_ls_wR_factor_gt          0.3738
_refine_ls_goodness_of_fit_ref   1.523
_refine_ls_restrained_S_all      1.523
_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
C1 C 0.2706(4) 1.0858(5) 0.45120(14) 0.0847(12) Uani 1 1 d . . .
C2 C 0.4233(3) 1.0715(5) 0.44107(12) 0.0719(11) Uani 1 1 d . . .
C3 C 0.4665(4) 0.9819(5) 0.40868(14) 0.0805(12) Uani 1 1 d . . .
H3 H 0.3958 0.9304 0.3931 0.097 Uiso 1 1 calc R . .
C4 C 0.6121(4) 0.9660(5) 0.39845(14) 0.0789(12) Uani 1 1 d . . .
H4 H 0.6390 0.9062 0.3759 0.095 Uiso 1 1 calc R . .
C5 C 0.7197(3) 1.0407(4) 0.42223(12) 0.0675(10) Uani 1 1 d . . .
C6 C 0.6745(4) 1.1308(5) 0.45536(13) 0.0743(11) Uani 1 1 d . . .
H6 H 0.7448 1.1805 0.4714 0.089 Uiso 1 1 calc R . .
C7 C 0.5301(4) 1.1481(5) 0.46496(12) 0.0764(11) Uani 1 1 d . . .
H7 H 0.5024 1.2098 0.4871 0.092 Uiso 1 1 calc R . .
C8 C 0.9316(4) 0.9250(5) 0.38507(15) 0.0836(12) Uani 1 1 d . . .
H8A H 0.8650 0.8370 0.3793 0.100 Uiso 1 1 calc R . .
H8B H 1.0205 0.8799 0.3965 0.100 Uiso 1 1 calc R . .
C9 C 0.9681(5) 1.0100(5) 0.34674(18) 0.0888(14) Uani 1 1 d . . .
C10 C 1.0377(5) 0.8961(6) 0.31592(18) 0.1040(16) Uani 1 1 d . . .
C11 C 1.0846(10) 0.9645(10) 0.2752(3) 0.145(3) Uani 1 1 d . . .
F1 F 0.8516(4) 1.0797(5) 0.33101(13) 0.1363(15) Uani 1 1 d . . .
F2 F 1.0634(4) 1.1294(4) 0.35389(13) 0.1383(15) Uani 1 1 d . . .
F3 F 0.9412(6) 0.7811(5) 0.30763(15) 0.190(2) Uani 1 1 d . . .
F4 F 1.1591(6) 0.8314(7) 0.33192(16) 0.195(3) Uani 1 1 d . . .
F5 F 1.1418(7) 0.8528(6) 0.25308(17) 0.188(2) Uani 1 1 d . . .
F6 F 1.1643(10) 1.0779(9) 0.2798(2) 0.282(5) Uani 1 1 d . . .
F7 F 0.9626(9) 1.0012(11) 0.2570(2) 0.253(4) Uani 1 1 d . . .
N1 N 0.1506(4) 1.1006(6) 0.45760(16) 0.1132(16) Uani 1 1 d . . .
N2 N 0.8659(4) 1.0297(4) 0.41364(12) 0.0844(11) 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
C1 0.061(2) 0.108(3) 0.085(3) -0.010(2) -0.0078(18) 0.0006(18)
C2 0.0564(19) 0.079(2) 0.080(3) 0.0001(18) -0.0045(16) -0.0007(15)
C3 0.062(2) 0.088(3) 0.092(3) -0.016(2) -0.0080(18) -0.0084(16)
C4 0.069(2) 0.078(2) 0.089(3) -0.019(2) -0.0010(19) -0.0013(16)
C5 0.0569(18) 0.064(2) 0.082(3) 0.0042(16) -0.0025(15) 0.0014(13)
C6 0.065(2) 0.089(2) 0.069(2) -0.0031(18) -0.0095(16) -0.0046(16)
C7 0.070(2) 0.093(3) 0.066(2) -0.0080(18) -0.0040(16) -0.0021(17)
C8 0.074(2) 0.074(2) 0.102(3) -0.001(2) 0.015(2) 0.0078(17)
C9 0.071(2) 0.085(3) 0.110(4) -0.004(2) 0.004(2) -0.0022(19)
C10 0.095(3) 0.104(4) 0.112(4) -0.012(3) 0.010(3) -0.011(3)
C11 0.131(6) 0.146(6) 0.158(7) 0.012(5) 0.016(5) -0.036(5)
F1 0.124(3) 0.143(3) 0.142(3) 0.036(2) 0.013(2) 0.050(2)
F2 0.158(3) 0.112(2) 0.145(3) -0.0325(19) 0.053(2) -0.056(2)
F3 0.266(5) 0.156(4) 0.147(3) -0.053(3) 0.072(3) -0.109(4)
F4 0.176(4) 0.251(6) 0.158(4) -0.031(3) -0.008(3) 0.139(4)
F5 0.241(5) 0.176(4) 0.148(4) -0.048(3) 0.070(4) 0.010(4)
F6 0.351(10) 0.271(7) 0.224(7) -0.092(6) 0.150(7) -0.192(8)
F7 0.202(6) 0.379(12) 0.179(6) 0.108(7) 0.014(5) 0.039(5)
N1 0.064(2) 0.161(4) 0.115(4) -0.030(3) -0.0063(19) 0.005(2)
N2 0.0621(17) 0.091(2) 0.100(3) -0.0103(18) 0.0034(15) 0.0029(15)

_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
C1 N1 1.122(5) . ?
C1 C2 1.438(5) . ?
C2 C3 1.365(6) . ?
C2 C7 1.408(5) . ?
C3 C4 1.377(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.404(6) . ?
C4 H4 0.9300 . ?
C5 N2 1.366(5) . ?
C5 C6 1.392(6) . ?
C6 C7 1.362(6) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C8 N2 1.420(6) . ?
C8 C9 1.492(7) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 F1 1.318(6) . ?
C9 F2 1.341(5) . ?
C9 C10 1.532(7) . ?
C10 F3 1.329(6) . ?
C10 F4 1.341(7) . ?
C10 C11 1.527(11) . ?
C11 F6 1.200(8) . ?
C11 F5 1.294(9) . ?
C11 F7 1.302(10) . ?

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
N1 C1 C2 177.0(5) . . ?
C3 C2 C7 119.4(3) . . ?
C3 C2 C1 120.5(3) . . ?
C7 C2 C1 120.1(4) . . ?
C2 C3 C4 121.6(4) . . ?
C2 C3 H3 119.2 . . ?
C4 C3 H3 119.2 . . ?
C3 C4 C5 119.6(4) . . ?
C3 C4 H4 120.2 . . ?
C5 C4 H4 120.2 . . ?
N2 C5 C6 119.3(3) . . ?
N2 C5 C4 122.4(4) . . ?
C6 C5 C4 118.3(3) . . ?
C7 C6 C5 121.9(4) . . ?
C7 C6 H6 119.1 . . ?
C5 C6 H6 119.1 . . ?
C6 C7 C2 119.3(4) . . ?
C6 C7 H7 120.4 . . ?
C2 C7 H7 120.4 . . ?
N2 C8 C9 111.8(4) . . ?
N2 C8 H8A 109.2 . . ?
C9 C8 H8A 109.2 . . ?
N2 C8 H8B 109.2 . . ?
C9 C8 H8B 109.2 . . ?
H8A C8 H8B 107.9 . . ?
F1 C9 F2 105.5(4) . . ?
F1 C9 C8 111.5(4) . . ?
F2 C9 C8 110.2(5) . . ?
F1 C9 C10 110.0(5) . . ?
F2 C9 C10 107.9(4) . . ?
C8 C9 C10 111.6(4) . . ?
F3 C10 F4 109.9(5) . . ?
F3 C10 C11 105.7(6) . . ?
F4 C10 C11 105.6(6) . . ?
F3 C10 C9 108.0(4) . . ?
F4 C10 C9 109.1(5) . . ?
C11 C10 C9 118.4(5) . . ?
F6 C11 F5 113.1(8) . . ?
F6 C11 F7 113.1(10) . . ?
F5 C11 F7 104.5(9) . . ?
F6 C11 C10 110.5(9) . . ?
F5 C11 C10 110.3(7) . . ?
F7 C11 C10 104.9(6) . . ?
C5 N2 C8 126.3(4) . . ?

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
N1 C1 C2 C3 -67(10) . . . . ?
N1 C1 C2 C7 114(10) . . . . ?
C7 C2 C3 C4 -0.8(6) . . . . ?
C1 C2 C3 C4 -179.8(4) . . . . ?
C2 C3 C4 C5 1.3(7) . . . . ?
C3 C4 C5 N2 -179.9(4) . . . . ?
C3 C4 C5 C6 -0.8(6) . . . . ?
N2 C5 C6 C7 178.9(3) . . . . ?
C4 C5 C6 C7 -0.2(6) . . . . ?
C5 C6 C7 C2 0.7(6) . . . . ?
C3 C2 C7 C6 -0.2(6) . . . . ?
C1 C2 C7 C6 178.8(4) . . . . ?
N2 C8 C9 F1 -56.0(5) . . . . ?
N2 C8 C9 F2 60.7(5) . . . . ?
N2 C8 C9 C10 -179.5(4) . . . . ?
F1 C9 C10 F3 -63.1(6) . . . . ?
F2 C9 C10 F3 -177.6(5) . . . . ?
C8 C9 C10 F3 61.2(6) . . . . ?
F1 C9 C10 F4 177.6(5) . . . . ?
F2 C9 C10 F4 63.0(6) . . . . ?
C8 C9 C10 F4 -58.2(6) . . . . ?
F1 C9 C10 C11 56.9(7) . . . . ?
F2 C9 C10 C11 -57.7(7) . . . . ?
C8 C9 C10 C11 -178.8(5) . . . . ?
F3 C10 C11 F6 175.0(9) . . . . ?
F4 C10 C11 F6 -68.6(10) . . . . ?
C9 C10 C11 F6 53.8(11) . . . . ?
F3 C10 C11 F5 -59.3(8) . . . . ?
F4 C10 C11 F5 57.2(8) . . . . ?
C9 C10 C11 F5 179.6(6) . . . . ?
F3 C10 C11 F7 52.8(8) . . . . ?
F4 C10 C11 F7 169.2(7) . . . . ?
C9 C10 C11 F7 -68.4(8) . . . . ?
C6 C5 N2 C8 170.0(4) . . . . ?
C4 C5 N2 C8 -11.0(6) . . . . ?
C9 C8 N2 C5 101.0(5) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.50
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.447
_refine_diff_density_min         -0.708
_refine_diff_density_rms         0.182
####################################################################### 
# 
# 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_a
_database_code_depnum_ccdc_archive 'CCDC 1853090'
_audit_update_record             
;
2018-07-03 deposited with the CCDC.
2018-08-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         C9H8F2N2
_chemical_formula_sum            'C9 H8 F2 N2'
_chemical_formula_weight         182.17

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
_symmetry_space_group_name_Hall  -P2yn

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                   4.3659(6)
_cell_length_b                   22.675(3)
_cell_length_c                   8.7400(12)
_cell_angle_alpha                90.00
_cell_angle_beta                 92.880(14)
_cell_angle_gamma                90.00
_cell_volume                     864.1(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3126
_cell_measurement_theta_min      4.2690
_cell_measurement_theta_max      25.8280

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.400
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             376
_exptl_absorpt_coefficient_mu    0.116
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9794
_exptl_absorpt_correction_T_max  0.9828
_exptl_absorpt_process_details   sadabs

_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  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8410
_diffrn_reflns_av_R_equivalents  0.0488
_diffrn_reflns_av_sigmaI/netI    0.0277
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         3.57
_diffrn_reflns_theta_max         25.50
_reflns_number_total             1603
_reflns_number_gt                1323
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_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)+(0.1435P)²+0.3179P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1603
_refine_ls_number_parameters     118
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0852
_refine_ls_R_factor_gt           0.0759
_refine_ls_wR_factor_ref         0.2120
_refine_ls_wR_factor_gt          0.1972
_refine_ls_goodness_of_fit_ref   0.975
_refine_ls_restrained_S_all      0.975
_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
C1 C 1.2179(7) 0.06946(12) 0.0066(3) 0.0585(7) Uani 1 1 d . . .
C2 C 1.1445(5) 0.08246(10) 0.1604(3) 0.0476(6) Uani 1 1 d . . .
C3 C 0.9558(6) 0.13014(11) 0.1906(3) 0.0529(7) Uani 1 1 d . . .
H3 H 0.8773 0.1533 0.1099 0.063 Uiso 1 1 calc R . .
C4 C 0.8843(6) 0.14348(11) 0.3372(3) 0.0509(6) Uani 1 1 d . . .
H4 H 0.7609 0.1759 0.3554 0.061 Uiso 1 1 calc R . .
C5 C 0.9955(5) 0.10868(9) 0.4598(2) 0.0414(6) Uani 1 1 d . . .
C6 C 1.1884(6) 0.06134(11) 0.4288(3) 0.0484(6) Uani 1 1 d . . .
H6 H 1.2687 0.0383 0.5092 0.058 Uiso 1 1 calc R . .
C7 C 1.2608(6) 0.04843(11) 0.2816(3) 0.0510(6) Uani 1 1 d . . .
H7 H 1.3886 0.0167 0.2630 0.061 Uiso 1 1 calc R . .
C8 C 0.7103(6) 0.16218(13) 0.6574(3) 0.0567(7) Uani 1 1 d . . .
H8A H 0.5994 0.1458 0.7408 0.068 Uiso 1 1 calc R . .
H8B H 0.5623 0.1703 0.5736 0.068 Uiso 1 1 calc R . .
C9 C 0.8536(6) 0.21874(13) 0.7093(4) 0.0650(8) Uani 1 1 d . . .
H9 H 0.6951 0.2467 0.7380 0.078 Uiso 1 1 calc R . .
F1 F 1.0582(4) 0.20963(9) 0.8299(2) 0.0845(7) Uani 1 1 d . . .
F2 F 1.0241(4) 0.24250(8) 0.5995(2) 0.0852(7) Uani 1 1 d . . .
N1 N 1.2742(7) 0.06010(13) -0.1179(3) 0.0776(8) Uani 1 1 d . . .
N2 N 0.9237(5) 0.11870(9) 0.6076(2) 0.0519(6) Uani 1 1 d . . .
H2 H 1.0139 0.0971 0.6772 0.062 Uiso 1 1 calc R . .

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
C1 0.0781(17) 0.0514(15) 0.0455(14) 0.0043(11) -0.0012(12) 0.0031(12)
C2 0.0585(14) 0.0438(13) 0.0401(12) 0.0014(9) -0.0030(10) -0.0070(10)
C3 0.0660(15) 0.0476(14) 0.0439(13) 0.0096(10) -0.0073(11) 0.0022(11)
C4 0.0572(14) 0.0457(13) 0.0493(13) 0.0053(10) -0.0023(10) 0.0061(10)
C5 0.0439(12) 0.0394(12) 0.0403(12) 0.0012(9) -0.0028(9) -0.0093(9)
C6 0.0608(14) 0.0430(13) 0.0405(12) 0.0056(9) -0.0053(10) 0.0014(10)
C7 0.0635(15) 0.0434(13) 0.0458(13) 0.0012(10) -0.0010(11) 0.0062(10)
C8 0.0463(13) 0.0703(18) 0.0537(15) -0.0073(12) 0.0054(11) -0.0032(11)
C9 0.0580(15) 0.0650(18) 0.0718(18) -0.0118(14) 0.0019(13) 0.0075(12)
F1 0.0937(13) 0.0838(13) 0.0736(12) -0.0208(9) -0.0210(10) -0.0057(9)
F2 0.1008(14) 0.0623(11) 0.0924(15) 0.0046(9) 0.0046(11) -0.0171(9)
N1 0.116(2) 0.0738(17) 0.0428(13) 0.0033(11) 0.0046(13) 0.0161(15)
N2 0.0632(13) 0.0510(12) 0.0413(11) 0.0002(9) 0.0015(9) 0.0016(9)

_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
C1 N1 1.147(3) . ?
C1 C2 1.428(3) . ?
C2 C7 1.386(3) . ?
C2 C3 1.392(4) . ?
C3 C4 1.368(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.398(3) . ?
C4 H4 0.9300 . ?
C5 N2 1.363(3) . ?
C5 C6 1.399(3) . ?
C6 C7 1.372(3) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C8 N2 1.439(3) . ?
C8 C9 1.488(4) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 F2 1.355(3) . ?
C9 F1 1.363(4) . ?
C9 H9 0.9800 . ?
N2 H2 0.8600 . ?

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
N1 C1 C2 178.6(3) . . ?
C7 C2 C3 119.0(2) . . ?
C7 C2 C1 120.9(2) . . ?
C3 C2 C1 120.1(2) . . ?
C4 C3 C2 121.0(2) . . ?
C4 C3 H3 119.5 . . ?
C2 C3 H3 119.5 . . ?
C3 C4 C5 120.4(2) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 H4 119.8 . . ?
N2 C5 C4 123.0(2) . . ?
N2 C5 C6 118.7(2) . . ?
C4 C5 C6 118.3(2) . . ?
C7 C6 C5 121.0(2) . . ?
C7 C6 H6 119.5 . . ?
C5 C6 H6 119.5 . . ?
C6 C7 C2 120.3(2) . . ?
C6 C7 H7 119.8 . . ?
C2 C7 H7 119.8 . . ?
N2 C8 C9 114.5(2) . . ?
N2 C8 H8A 108.6 . . ?
C9 C8 H8A 108.6 . . ?
N2 C8 H8B 108.6 . . ?
C9 C8 H8B 108.6 . . ?
H8A C8 H8B 107.6 . . ?
F2 C9 F1 104.2(2) . . ?
F2 C9 C8 111.3(2) . . ?
F1 C9 C8 110.8(3) . . ?
F2 C9 H9 110.1 . . ?
F1 C9 H9 110.1 . . ?
C8 C9 H9 110.1 . . ?
C5 N2 C8 125.7(2) . . ?
C5 N2 H2 117.1 . . ?
C8 N2 H2 117.1 . . ?

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
N1 C1 C2 C7 -170(100) . . . . ?
N1 C1 C2 C3 9(14) . . . . ?
C7 C2 C3 C4 -0.2(4) . . . . ?
C1 C2 C3 C4 -179.6(2) . . . . ?
C2 C3 C4 C5 -1.1(4) . . . . ?
C3 C4 C5 N2 -177.8(2) . . . . ?
C3 C4 C5 C6 2.0(4) . . . . ?
N2 C5 C6 C7 178.2(2) . . . . ?
C4 C5 C6 C7 -1.6(3) . . . . ?
C5 C6 C7 C2 0.3(4) . . . . ?
C3 C2 C7 C6 0.6(4) . . . . ?
C1 C2 C7 C6 -180.0(2) . . . . ?
N2 C8 C9 F2 55.5(3) . . . . ?
N2 C8 C9 F1 -60.0(3) . . . . ?
C4 C5 N2 C8 5.1(4) . . . . ?
C6 C5 N2 C8 -174.6(2) . . . . ?
C9 C8 N2 C5 -96.0(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.50
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.324
_refine_diff_density_min         -0.344
_refine_diff_density_rms         0.095
