# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# 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_find

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H8 F2 N2 O2'
_chemical_formula_weight         298.24

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

_symmetry_cell_setting           Monoclinic

_symmetry_space_group_name_H-M   P2(1)/c

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

_cell_length_a                   8.2730(10)
_cell_length_b                   6.0598(4)
_cell_length_c                   12.2500(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 101.070(10)
_cell_angle_gamma                90.00
_cell_volume                     602.70(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    6353
_cell_measurement_theta_min      5
_cell_measurement_theta_max      32

_exptl_crystal_description       plate
_exptl_crystal_colour            black
_exptl_crystal_size_max          0.03
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.005
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.643
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             304
_exptl_absorpt_coefficient_mu    0.131
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.85507
_diffrn_radiation_type           synchrotron
_diffrn_radiation_source         'BL 14.2 PSF, BESSY, Berlin, Germany'
_diffrn_radiation_monochromator  Si(111)
_diffrn_measurement_device_type  MAR225
_diffrn_measurement_method       CCD
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8834
_diffrn_reflns_av_R_equivalents  0.0485
_diffrn_reflns_av_sigmaI/netI    0.0334
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         4.53
_diffrn_reflns_theta_max         34.73
_reflns_number_total             1409
_reflns_number_gt                1216
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       XDS
_computing_cell_refinement       XDS
_computing_data_reduction        XDS
_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.
 The molecule is located on an inversion center. 
;

_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)+(0.0900P)²+0.3000P] 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         1409
_refine_ls_number_parameters     100
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0611
_refine_ls_R_factor_gt           0.0530
_refine_ls_wR_factor_ref         0.1497
_refine_ls_wR_factor_gt          0.1440
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_restrained_S_all      1.045
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.94112(14) 0.12607(18) 0.14663(10) 0.0385(3) Uani 1 1 d . . .
O1 O 0.56379(15) 0.8686(2) -0.19216(10) 0.0298(3) Uani 1 1 d . . .
N1 N 0.61242(17) 0.7885(2) 0.09574(11) 0.0263(4) Uani 1 1 d . . .
H1 H 0.6005 0.8205 0.1638 0.032 Uiso 1 1 calc R . .
C1 C 0.54764(19) 0.9084(3) 0.00154(13) 0.0252(4) Uani 1 1 d . . .
C2 C 0.59981(19) 0.8017(3) -0.09532(13) 0.0244(4) Uani 1 1 d . . .
C3 C 0.6963(2) 0.6106(3) -0.04915(14) 0.0264(4) Uani 1 1 d . . .
C4 C 0.7760(2) 0.4455(3) -0.09835(15) 0.0290(4) Uani 1 1 d . . .
H4 H 0.7734 0.4460 -0.1762 0.035 Uiso 1 1 calc R . .
C5 C 0.8589(2) 0.2808(3) -0.03140(15) 0.0308(4) Uani 1 1 d . . .
H5 H 0.9145 0.1663 -0.0622 0.037 Uiso 1 1 calc R . .
C6 C 0.8586(2) 0.2878(3) 0.08221(15) 0.0301(4) Uani 1 1 d . . .
C7 C 0.7810(2) 0.4460(3) 0.13525(14) 0.0284(4) Uani 1 1 d . . .
H7 H 0.7835 0.4432 0.2131 0.034 Uiso 1 1 calc R . .
C8 C 0.69887(19) 0.6101(3) 0.06600(14) 0.0257(4) 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
F1 0.0484(7) 0.0329(6) 0.0337(7) 0.0053(4) 0.0069(5) 0.0131(4)
O1 0.0407(7) 0.0297(6) 0.0196(7) -0.0006(4) 0.0076(5) 0.0014(5)
N1 0.0372(7) 0.0249(7) 0.0178(7) -0.0003(5) 0.0076(5) 0.0015(5)
C1 0.0325(8) 0.0238(7) 0.0197(8) -0.0007(5) 0.0061(6) -0.0027(6)
C2 0.0308(7) 0.0243(7) 0.0188(8) -0.0018(5) 0.0068(5) -0.0030(6)
C3 0.0313(8) 0.0257(8) 0.0225(8) -0.0020(6) 0.0062(6) -0.0022(6)
C4 0.0346(8) 0.0295(8) 0.0234(8) -0.0042(6) 0.0071(6) -0.0007(6)
C5 0.0334(8) 0.0272(8) 0.0323(10) -0.0042(6) 0.0080(7) 0.0022(6)
C6 0.0333(8) 0.0267(8) 0.0294(9) 0.0018(6) 0.0044(6) 0.0020(6)
C7 0.0347(8) 0.0279(8) 0.0230(8) 0.0010(6) 0.0065(6) -0.0001(6)
C8 0.0298(8) 0.0243(7) 0.0233(9) -0.0014(5) 0.0055(6) -0.0022(6)

_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 C6 1.3572(19) . ?
O1 C2 1.235(2) . ?
N1 C1 1.382(2) . ?
N1 C8 1.383(2) . ?
C1 C1 1.357(3) 3_675 ?
C1 C2 1.486(2) . ?
C2 C3 1.458(2) . ?
C3 C4 1.397(2) . ?
C3 C8 1.407(2) . ?
C4 C5 1.387(2) . ?
C5 C6 1.393(3) . ?
C6 C7 1.383(2) . ?
C7 C8 1.396(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C8 109.17(13) . . ?
C1 C1 N1 125.68(19) 3_675 . ?
C1 C1 C2 126.13(19) 3_675 . ?
N1 C1 C2 108.19(13) . . ?
O1 C2 C3 130.30(15) . . ?
O1 C2 C1 124.79(15) . . ?
C3 C2 C1 104.92(14) . . ?
C4 C3 C8 120.91(15) . . ?
C4 C3 C2 132.09(16) . . ?
C8 C3 C2 107.00(14) . . ?
C5 C4 C3 118.76(16) . . ?
C4 C5 C6 118.26(15) . . ?
F1 C6 C7 117.02(16) . . ?
F1 C6 C5 117.51(15) . . ?
C7 C6 C5 125.47(16) . . ?
C6 C7 C8 115.08(16) . . ?
N1 C8 C7 127.78(15) . . ?
N1 C8 C3 110.71(14) . . ?
C7 C8 C3 121.52(15) . . ?

_diffrn_measured_fraction_theta_max 0.944
_diffrn_reflns_theta_full        30.55
_diffrn_measured_fraction_theta_full 0.956
_refine_diff_density_max         0.343
_refine_diff_density_min         -0.261
_refine_diff_density_rms         0.059
_database_code_depnum_ccdc_archive 'CCDC 991835'
#######################################################################
#
#                 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_cf3inda

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H8 F6 N2 O2'
_chemical_formula_weight         398.26

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   Iba2

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

_cell_length_a                   28.2110(10)
_cell_length_b                   8.6741(7)
_cell_length_c                   12.6299(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     3090.6(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    10000
_cell_measurement_theta_min      5
_cell_measurement_theta_max      32

_exptl_crystal_description       needle
_exptl_crystal_colour            blue
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.01
_exptl_crystal_size_min          0.01
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.712
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1600
_exptl_absorpt_coefficient_mu    0.247
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.84344
_diffrn_radiation_source         'BL 14.2, PSF, BESSY, Berlin, Germany'
_diffrn_radiation_monochromator  Si(111)
_diffrn_measurement_device_type  MAR225
_diffrn_measurement_method       CCD
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            24964
_diffrn_reflns_av_R_equivalents  0.0248
_diffrn_reflns_av_sigmaI/netI    0.0150
_diffrn_reflns_limit_h_min       -37
_diffrn_reflns_limit_h_max       37
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.92
_diffrn_reflns_theta_max         34.71
_reflns_number_total             3750
_reflns_number_gt                3703
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       XDS
_computing_cell_refinement       XDS
_computing_data_reduction        XDS
_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)+(0.1000P)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    restrain
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.035(2)
_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   -0.2(4)
_refine_ls_number_reflns         3750
_refine_ls_number_parameters     254
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0396
_refine_ls_R_factor_gt           0.0392
_refine_ls_wR_factor_ref         0.1084
_refine_ls_wR_factor_gt          0.1078
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_restrained_S_all      1.067
_refine_ls_shift/su_max          0.011
_refine_ls_shift/su_mean         0.002

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 0.68660(3) 0.46573(12) 0.60568(9) 0.0291(2) Uani 1 1 d . . .
F2 F 0.63353(4) 0.33067(11) 0.68578(10) 0.0324(3) Uani 1 1 d . . .
F3 F 0.65380(3) 0.55213(11) 0.74723(9) 0.0256(2) Uani 1 1 d . . .
F4 F 0.25869(4) 1.20485(12) 0.27801(9) 0.0310(2) Uani 1 1 d . . .
F5 F 0.21513(3) 1.24602(12) 0.41511(9) 0.0282(2) Uani 1 1 d . . .
F6 F 0.26867(4) 1.41023(10) 0.37084(11) 0.0329(3) Uani 1 1 d . . .
O1 O 0.48400(3) 0.79319(13) 0.33883(9) 0.0193(2) Uani 1 1 d . . .
O2 O 0.41785(4) 0.95730(11) 0.71163(8) 0.0181(2) Uani 1 1 d . . .
N1 N 0.49707(4) 0.78166(13) 0.61511(10) 0.0148(2) Uani 1 1 d . . .
H1 H 0.4896 0.8027 0.6812 0.018 Uiso 1 1 calc R . .
N2 N 0.40826(4) 0.96205(12) 0.43506(10) 0.0149(2) Uani 1 1 d . . .
H2 H 0.4176 0.9442 0.3697 0.018 Uiso 1 1 calc R . .
C1 C 0.47218(4) 0.82997(13) 0.52690(11) 0.0133(2) Uani 1 1 d . . .
C2 C 0.49667(4) 0.76996(14) 0.43050(12) 0.0139(2) Uani 1 1 d . . .
C3 C 0.53712(4) 0.68286(14) 0.47259(12) 0.0150(3) Uani 1 1 d . . .
C4 C 0.57319(5) 0.60259(15) 0.42050(11) 0.0180(3) Uani 1 1 d . . .
H4 H 0.5736 0.5943 0.3455 0.022 Uiso 1 1 calc R . .
C5 C 0.60868(5) 0.53487(15) 0.48194(13) 0.0192(3) Uani 1 1 d . . .
H5 H 0.6338 0.4796 0.4492 0.023 Uiso 1 1 calc R . .
C6 C 0.60683(4) 0.54926(14) 0.59201(12) 0.0152(3) Uani 1 1 d . . .
C7 C 0.57110(4) 0.62788(15) 0.64576(12) 0.0153(3) Uani 1 1 d . . .
H7 H 0.5707 0.6357 0.7208 0.018 Uiso 1 1 calc R . .
C8 C 0.53574(4) 0.69468(14) 0.58292(12) 0.0132(3) Uani 1 1 d . . .
C9 C 0.64558(5) 0.47552(16) 0.65715(13) 0.0191(3) Uani 1 1 d . . .
C10 C 0.43176(4) 0.91592(13) 0.52503(11) 0.0138(2) Uani 1 1 d . . .
C11 C 0.40517(4) 0.97259(14) 0.61937(12) 0.0140(2) Uani 1 1 d . . .
C12 C 0.36298(5) 1.04800(15) 0.57421(11) 0.0146(3) Uani 1 1 d . . .
C13 C 0.32390(5) 1.11924(15) 0.62163(12) 0.0171(3) Uani 1 1 d . . .
H13 H 0.3208 1.1235 0.6965 0.021 Uiso 1 1 calc R . .
C14 C 0.28972(5) 1.18356(15) 0.55590(12) 0.0175(3) Uani 1 1 d . . .
H14 H 0.2625 1.2315 0.5856 0.021 Uiso 1 1 calc R . .
C15 C 0.29535(4) 1.17768(14) 0.44590(12) 0.0158(3) Uani 1 1 d . . .
C16 C 0.33394(4) 1.10878(14) 0.39698(12) 0.0158(3) Uani 1 1 d . . .
H16 H 0.3373 1.1076 0.3222 0.019 Uiso 1 1 calc R . .
C17 C 0.36757(4) 1.04117(14) 0.46369(12) 0.0144(3) Uani 1 1 d . . .
C18 C 0.25951(5) 1.25884(17) 0.37708(13) 0.0203(3) 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
F1 0.0191(4) 0.0424(5) 0.0259(6) 0.0087(4) 0.0042(4) 0.0118(3)
F2 0.0343(5) 0.0219(4) 0.0409(7) 0.0131(4) -0.0061(4) 0.0006(3)
F3 0.0229(4) 0.0339(4) 0.0200(5) -0.0006(4) -0.0068(4) 0.0070(3)
F4 0.0303(5) 0.0408(5) 0.0220(6) 0.0046(4) -0.0066(4) 0.0115(4)
F5 0.0134(4) 0.0361(5) 0.0351(6) 0.0107(4) 0.0007(4) 0.0023(3)
F6 0.0282(5) 0.0190(4) 0.0515(8) 0.0116(4) -0.0016(4) 0.0036(3)
O1 0.0175(4) 0.0306(5) 0.0100(6) -0.0006(4) -0.0011(3) 0.0031(4)
O2 0.0189(4) 0.0243(5) 0.0111(6) -0.0009(3) -0.0002(3) 0.0008(3)
N1 0.0146(4) 0.0215(5) 0.0085(6) -0.0008(3) 0.0000(4) 0.0031(4)
N2 0.0140(5) 0.0224(5) 0.0083(6) 0.0000(4) -0.0012(4) 0.0029(4)
C1 0.0138(5) 0.0178(5) 0.0083(6) -0.0020(4) -0.0001(4) -0.0009(4)
C2 0.0136(5) 0.0186(5) 0.0094(6) -0.0004(4) -0.0002(4) -0.0001(4)
C3 0.0152(5) 0.0188(5) 0.0110(7) -0.0003(4) 0.0004(4) -0.0003(4)
C4 0.0199(6) 0.0235(6) 0.0107(7) -0.0036(4) 0.0020(5) 0.0031(4)
C5 0.0173(6) 0.0210(6) 0.0193(8) -0.0017(5) 0.0022(5) 0.0039(4)
C6 0.0152(5) 0.0152(5) 0.0153(7) 0.0021(4) -0.0003(4) 0.0003(4)
C7 0.0146(5) 0.0187(5) 0.0127(6) 0.0012(4) -0.0001(4) 0.0000(4)
C8 0.0126(5) 0.0157(5) 0.0115(7) -0.0006(4) 0.0008(4) 0.0004(4)
C9 0.0177(6) 0.0208(6) 0.0188(8) 0.0048(5) -0.0001(5) 0.0018(4)
C10 0.0148(5) 0.0190(5) 0.0075(6) -0.0008(4) 0.0006(4) -0.0017(4)
C11 0.0149(5) 0.0150(5) 0.0121(7) -0.0028(4) 0.0027(4) -0.0019(4)
C12 0.0148(5) 0.0170(5) 0.0120(7) 0.0005(4) -0.0002(4) -0.0016(4)
C13 0.0181(5) 0.0211(5) 0.0122(6) -0.0019(4) 0.0018(5) 0.0007(4)
C14 0.0152(5) 0.0188(5) 0.0187(8) -0.0011(4) 0.0015(4) 0.0009(4)
C15 0.0139(5) 0.0143(5) 0.0193(7) 0.0015(4) -0.0003(4) -0.0011(4)
C16 0.0144(5) 0.0176(5) 0.0155(7) 0.0003(4) 0.0010(4) -0.0007(4)
C17 0.0140(5) 0.0149(5) 0.0142(7) 0.0008(4) 0.0024(4) -0.0012(4)
C18 0.0152(6) 0.0229(6) 0.0229(8) 0.0064(5) 0.0011(5) 0.0021(4)

_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 C9 1.3298(17) . ?
F2 C9 1.3510(16) . ?
F3 C9 1.3378(19) . ?
F4 C18 1.336(2) . ?
F5 C18 1.3457(15) . ?
F6 C18 1.3407(16) . ?
O1 C2 1.2284(19) . ?
O2 C11 1.226(2) . ?
N1 C1 1.3819(17) . ?
N1 C8 1.3874(15) . ?
N2 C10 1.3750(17) . ?
N2 C17 1.3855(15) . ?
C1 C10 1.3626(16) . ?
C1 C2 1.4935(18) . ?
C2 C3 1.4681(17) . ?
C3 C4 1.3976(17) . ?
C3 C8 1.398(2) . ?
C4 C5 1.3963(19) . ?
C5 C6 1.397(2) . ?
C6 C7 1.3936(18) . ?
C6 C9 1.5103(19) . ?
C7 C8 1.4001(17) . ?
C10 C11 1.4913(18) . ?
C11 C12 1.4729(18) . ?
C12 C13 1.3986(18) . ?
C12 C17 1.403(2) . ?
C13 C14 1.3893(19) . ?
C14 C15 1.399(2) . ?
C15 C16 1.3873(18) . ?
C15 C18 1.5077(18) . ?
C16 C17 1.3977(18) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C8 109.16(12) . . ?
C10 N2 C17 109.15(12) . . ?
C10 C1 N1 127.23(12) . . ?
C10 C1 C2 124.31(12) . . ?
N1 C1 C2 108.45(10) . . ?
O1 C2 C3 130.68(13) . . ?
O1 C2 C1 125.21(12) . . ?
C3 C2 C1 104.10(12) . . ?
C4 C3 C8 121.74(13) . . ?
C4 C3 C2 130.68(14) . . ?
C8 C3 C2 107.56(12) . . ?
C5 C4 C3 118.04(13) . . ?
C4 C5 C6 119.25(12) . . ?
C7 C6 C5 123.75(13) . . ?
C7 C6 C9 117.75(13) . . ?
C5 C6 C9 118.50(12) . . ?
C6 C7 C8 116.21(13) . . ?
N1 C8 C3 110.72(12) . . ?
N1 C8 C7 128.25(13) . . ?
C3 C8 C7 121.00(12) . . ?
F1 C9 F3 107.26(12) . . ?
F1 C9 F2 106.89(12) . . ?
F3 C9 F2 106.14(13) . . ?
F1 C9 C6 112.99(13) . . ?
F3 C9 C6 112.23(11) . . ?
F2 C9 C6 110.95(12) . . ?
C1 C10 N2 125.24(12) . . ?
C1 C10 C11 125.98(12) . . ?
N2 C10 C11 108.77(11) . . ?
O2 C11 C12 130.67(12) . . ?
O2 C11 C10 125.23(12) . . ?
C12 C11 C10 104.10(12) . . ?
C13 C12 C17 121.16(13) . . ?
C13 C12 C11 131.87(14) . . ?
C17 C12 C11 106.97(12) . . ?
C14 C13 C12 117.95(13) . . ?
C13 C14 C15 119.99(12) . . ?
C16 C15 C14 123.15(13) . . ?
C16 C15 C18 118.08(14) . . ?
C14 C15 C18 118.64(13) . . ?
C15 C16 C17 116.43(13) . . ?
N2 C17 C16 127.80(14) . . ?
N2 C17 C12 110.91(12) . . ?
C16 C17 C12 121.28(12) . . ?
F4 C18 F6 106.95(13) . . ?
F4 C18 F5 106.81(12) . . ?
F6 C18 F5 106.33(12) . . ?
F4 C18 C15 112.82(12) . . ?
F6 C18 C15 111.22(12) . . ?
F5 C18 C15 112.31(12) . . ?

_diffrn_measured_fraction_theta_max 0.954
_diffrn_reflns_theta_full        30.10
_diffrn_measured_fraction_theta_full 0.969
_refine_diff_density_max         0.446
_refine_diff_density_min         -0.263
_refine_diff_density_rms         0.062
_database_code_depnum_ccdc_archive 'CCDC 991836'
#######################################################################
#
#                 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_55find

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H8 F2 N2 O2'
_chemical_formula_weight         298.24

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

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

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

_cell_length_a                   8.2490(10)
_cell_length_b                   6.0281(7)
_cell_length_c                   12.2840(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 94.350(10)
_cell_angle_gamma                90.00
_cell_volume                     609.07(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    5000
_cell_measurement_theta_min      5
_cell_measurement_theta_max      35

_exptl_crystal_description       plate
_exptl_crystal_colour            black
_exptl_crystal_size_max          0.03
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.01
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.626
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             304
_exptl_absorpt_coefficient_mu    0.195
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.84344
_diffrn_radiation_type           synchrotron
_diffrn_radiation_source         'BL 14.2, PSF, BESSY, Berlin, Germany'
_diffrn_radiation_monochromator  Si(111)
_diffrn_measurement_device_type  MAR225
_diffrn_measurement_method       CCD
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            9551
_diffrn_reflns_av_R_equivalents  0.0334
_diffrn_reflns_av_sigmaI/netI    0.0204
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         4.47
_diffrn_reflns_theta_max         36.59
_reflns_number_total             1511
_reflns_number_gt                1346
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       XDS
_computing_cell_refinement       XDS
_computing_data_reduction        XDS
_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. 
 The molecule is located on an inversion centre.
;

_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)+(0.0600P)²+0.6000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.84(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         1511
_refine_ls_number_parameters     117
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0603
_refine_ls_R_factor_gt           0.0539
_refine_ls_wR_factor_ref         0.1396
_refine_ls_wR_factor_gt          0.1358
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_restrained_S_all      1.033
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.94086(17) 0.1363(2) 0.29730(9) 0.0299(4) Uani 1 1 d . . .
N1 N 0.88431(19) 0.2088(2) 0.57507(11) 0.0268(4) Uani 1 1 d . . .
F1 F 0.56840(19) 0.8829(2) 0.34598(12) 0.0511(5) Uani 1 1 d . . .
C1 C 0.9524(2) 0.0919(3) 0.49344(13) 0.0248(4) Uani 1 1 d . . .
C2 C 0.9036(2) 0.2011(3) 0.38721(13) 0.0252(4) Uani 1 1 d . . .
C3 C 0.8066(2) 0.3925(3) 0.41590(13) 0.0271(4) Uani 1 1 d . . .
C4 C 0.7289(2) 0.5577(3) 0.35118(15) 0.0322(5) Uani 1 1 d . . .
C5 C 0.6482(2) 0.7179(3) 0.40567(16) 0.0335(5) Uani 1 1 d . . .
C6 C 0.6414(2) 0.7204(3) 0.51925(16) 0.0323(5) Uani 1 1 d . . .
C7 C 0.7186(2) 0.5561(3) 0.58312(14) 0.0297(4) Uani 1 1 d . . .
C8 C 0.8012(2) 0.3913(3) 0.53000(13) 0.0257(4) Uani 1 1 d . . .
H1 H 0.912(3) 0.201(5) 0.643(2) 0.043(7) Uiso 1 1 d . . .
H4 H 0.729(3) 0.556(4) 0.272(2) 0.039(6) Uiso 1 1 d . . .
H6 H 0.586(3) 0.843(4) 0.5549(19) 0.033(6) Uiso 1 1 d . . .
H7 H 0.717(3) 0.556(4) 0.6623(18) 0.024(5) Uiso 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 0.0426(8) 0.0307(7) 0.0166(6) 0.0009(4) 0.0039(5) 0.0026(5)
N1 0.0374(9) 0.0263(7) 0.0168(7) -0.0013(5) 0.0029(5) 0.0009(6)
F1 0.0656(10) 0.0426(8) 0.0470(8) 0.0133(6) 0.0167(6) 0.0203(6)
C1 0.0330(9) 0.0246(8) 0.0171(7) -0.0004(5) 0.0030(6) -0.0032(6)
C2 0.0319(9) 0.0240(8) 0.0197(8) 0.0013(6) 0.0022(6) -0.0016(6)
C3 0.0332(9) 0.0257(8) 0.0228(8) 0.0010(6) 0.0049(6) -0.0009(6)
C4 0.0380(11) 0.0310(9) 0.0282(9) 0.0050(7) 0.0072(7) 0.0028(7)
C5 0.0372(10) 0.0288(9) 0.0350(10) 0.0062(7) 0.0059(7) 0.0041(7)
C6 0.0340(10) 0.0266(9) 0.0370(10) -0.0024(7) 0.0072(7) 0.0007(7)
C7 0.0348(10) 0.0285(9) 0.0260(8) -0.0043(6) 0.0047(6) -0.0026(6)
C8 0.0304(9) 0.0240(8) 0.0229(8) -0.0010(6) 0.0033(6) -0.0029(6)

_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 C2 1.232(2) . ?
N1 C1 1.379(2) . ?
N1 C8 1.389(2) . ?
F1 C5 1.374(2) . ?
C1 C1 1.361(3) 3_756 ?
C1 C2 1.490(2) . ?
C2 C3 1.462(2) . ?
C3 C4 1.399(2) . ?
C3 C8 1.406(2) . ?
C4 C5 1.375(3) . ?
C5 C6 1.401(3) . ?
C6 C7 1.388(3) . ?
C7 C8 1.394(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C8 109.31(14) . . ?
C1 C1 N1 126.37(19) 3_756 . ?
C1 C1 C2 125.39(19) 3_756 . ?
N1 C1 C2 108.24(14) . . ?
O1 C2 C3 130.14(15) . . ?
O1 C2 C1 125.13(16) . . ?
C3 C2 C1 104.73(14) . . ?
C4 C3 C8 121.51(16) . . ?
C4 C3 C2 131.30(15) . . ?
C8 C3 C2 107.18(14) . . ?
C5 C4 C3 116.17(17) . . ?
F1 C5 C4 118.61(17) . . ?
F1 C5 C6 118.04(17) . . ?
C4 C5 C6 123.34(17) . . ?
C7 C6 C5 120.28(17) . . ?
C6 C7 C8 117.61(16) . . ?
N1 C8 C7 128.45(15) . . ?
N1 C8 C3 110.46(15) . . ?
C7 C8 C3 121.09(16) . . ?

_diffrn_measured_fraction_theta_max 0.836
_diffrn_reflns_theta_full        30.10
_diffrn_measured_fraction_theta_full 0.959
_refine_diff_density_max         0.415
_refine_diff_density_min         -0.380
_refine_diff_density_rms         0.056
_database_code_depnum_ccdc_archive 'CCDC 991837'
#######################################################################
#
#                 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_diclindf

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H8 Cl2 N2 O2'
_chemical_formula_weight         331.14

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

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

_cell_length_a                   13.1129(8)
_cell_length_b                   4.5375(2)
_cell_length_c                   11.7091(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 110.090(5)
_cell_angle_gamma                90.00
_cell_volume                     654.30(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    5514
_cell_measurement_theta_min      4
_cell_measurement_theta_max      29

_exptl_crystal_description       plate
_exptl_crystal_colour            black
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.02
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.681
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             336
_exptl_absorpt_coefficient_mu    0.504
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  IPDS(Stoe)
_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            9060
_diffrn_reflns_av_R_equivalents  0.1114
_diffrn_reflns_av_sigmaI/netI    0.0638
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.31
_diffrn_reflns_theta_max         29.15
_reflns_number_total             1748
_reflns_number_gt                1352
_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. 
 The molecule is located on an inversion centre.
;

_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)+(0.0300P)²+1.3000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1748
_refine_ls_number_parameters     116
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0814
_refine_ls_R_factor_gt           0.0579
_refine_ls_wR_factor_ref         0.1194
_refine_ls_wR_factor_gt          0.1125
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_restrained_S_all      1.063
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.94730(6) 0.21264(16) 0.86998(6) 0.02176(19) Uani 1 1 d . . .
O1 O 0.58334(16) 1.0297(4) 0.73829(16) 0.0169(4) Uani 1 1 d . . .
N1 N 0.59110(18) 0.7235(5) 0.46722(19) 0.0151(4) Uani 1 1 d . . .
C1 C 0.5435(2) 0.9120(6) 0.5264(2) 0.0150(5) Uani 1 1 d . . .
C2 C 0.6045(2) 0.8912(6) 0.6593(2) 0.0154(5) Uani 1 1 d . . .
C3 C 0.6902(2) 0.6753(6) 0.6694(2) 0.0150(5) Uani 1 1 d . . .
C4 C 0.7738(2) 0.5668(6) 0.7698(2) 0.0159(5) Uani 1 1 d . . .
C5 C 0.8425(2) 0.3616(6) 0.7484(2) 0.0179(6) Uani 1 1 d . . .
C6 C 0.8303(2) 0.2651(7) 0.6304(2) 0.0187(5) Uani 1 1 d . . .
C7 C 0.7482(2) 0.3757(6) 0.5303(2) 0.0169(5) Uani 1 1 d . . .
C8 C 0.6780(2) 0.5817(6) 0.5512(2) 0.0153(5) Uani 1 1 d . . .
H1 H 0.566(3) 0.689(9) 0.385(4) 0.037(11) Uiso 1 1 d . . .
H4 H 0.780(3) 0.640(8) 0.850(3) 0.027(9) Uiso 1 1 d . . .
H6 H 0.884(3) 0.140(8) 0.621(3) 0.022(9) Uiso 1 1 d . . .
H7 H 0.739(2) 0.307(7) 0.446(3) 0.012(7) Uiso 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
Cl1 0.0184(3) 0.0236(4) 0.0204(3) 0.0048(3) 0.0029(2) 0.0030(3)
O1 0.0242(10) 0.0162(10) 0.0122(8) -0.0003(7) 0.0088(7) 0.0008(8)
N1 0.0195(11) 0.0148(11) 0.0110(9) 0.0002(8) 0.0052(8) 0.0015(9)
C1 0.0216(14) 0.0129(12) 0.0118(11) 0.0000(10) 0.0072(10) -0.0024(10)
C2 0.0197(13) 0.0136(12) 0.0125(11) 0.0017(10) 0.0048(10) -0.0014(10)
C3 0.0200(12) 0.0135(12) 0.0127(11) 0.0008(9) 0.0072(9) -0.0026(10)
C4 0.0186(13) 0.0153(13) 0.0140(11) 0.0014(10) 0.0057(10) -0.0021(10)
C5 0.0177(12) 0.0170(14) 0.0160(12) 0.0038(10) 0.0019(10) -0.0012(10)
C6 0.0189(12) 0.0177(14) 0.0200(12) 0.0016(11) 0.0072(10) 0.0024(11)
C7 0.0205(13) 0.0166(13) 0.0142(11) -0.0003(10) 0.0068(10) -0.0002(10)
C8 0.0181(12) 0.0152(12) 0.0135(11) 0.0014(10) 0.0064(10) -0.0024(10)

_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 C5 1.740(3) . ?
O1 C2 1.226(3) . ?
N1 C1 1.378(3) . ?
N1 C8 1.382(3) . ?
C1 C1 1.356(5) 3_676 ?
C1 C2 1.488(4) . ?
C2 C3 1.465(4) . ?
C3 C4 1.393(4) . ?
C3 C8 1.404(3) . ?
C4 C5 1.377(4) . ?
C5 C6 1.406(4) . ?
C6 C7 1.385(4) . ?
C7 C8 1.390(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
C1 N1 C8 109.7(2) . . ?
C1 C1 N1 126.3(3) 3_676 . ?
C1 C1 C2 125.5(3) 3_676 . ?
N1 C1 C2 108.3(2) . . ?
O1 C2 C3 130.4(2) . . ?
O1 C2 C1 125.2(3) . . ?
C3 C2 C1 104.4(2) . . ?
C4 C3 C8 121.0(3) . . ?
C4 C3 C2 131.6(2) . . ?
C8 C3 C2 107.3(2) . . ?
C5 C4 C3 117.4(2) . . ?
C4 C5 C6 122.0(3) . . ?
C4 C5 Cl1 119.7(2) . . ?
C6 C5 Cl1 118.3(2) . . ?
C7 C6 C5 120.7(3) . . ?
C6 C7 C8 117.7(3) . . ?
N1 C8 C7 128.5(2) . . ?
N1 C8 C3 110.3(2) . . ?
C7 C8 C3 121.2(3) . . ?

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.991
_refine_diff_density_max         0.530
_refine_diff_density_min         -0.307
_refine_diff_density_rms         0.085
_database_code_depnum_ccdc_archive 'CCDC 991838'
#######################################################################
#
#                 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_4find

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H6 F4 N2 O2'
_chemical_formula_weight         334.23

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

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

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

_cell_length_a                   12.7080(10)
_cell_length_b                   4.6341(4)
_cell_length_c                   11.5960(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 115.352(7)
_cell_angle_gamma                90.00
_cell_volume                     617.12(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    4999
_cell_measurement_theta_min      5
_cell_measurement_theta_max      33

_exptl_crystal_description       needle
_exptl_crystal_colour            black
_exptl_crystal_size_max          0.03
_exptl_crystal_size_mid          0.01
_exptl_crystal_size_min          0.01
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.799
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             336
_exptl_absorpt_coefficient_mu    0.161
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.85507
_diffrn_radiation_type           synchrotron
_diffrn_radiation_source         'BL 14.2 PSF, BESSY, Berlin, Germany'
_diffrn_radiation_monochromator  Si(111)
_diffrn_measurement_device_type  MAR225
_diffrn_measurement_method       CCD
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            7911
_diffrn_reflns_av_R_equivalents  0.0639
_diffrn_reflns_av_sigmaI/netI    0.0421
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         5.79
_diffrn_reflns_theta_max         36.45
_reflns_number_total             1315
_reflns_number_gt                1162
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       XDS
_computing_cell_refinement       XDS
_computing_data_reduction        XDS
_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. 
 The molecule is located on an inversion centre.
;

_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)+(0.0500P)²+1.0000P] 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         1315
_refine_ls_number_parameters     113
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0732
_refine_ls_R_factor_gt           0.0643
_refine_ls_wR_factor_ref         0.1543
_refine_ls_wR_factor_gt          0.1507
_refine_ls_goodness_of_fit_ref   1.156
_refine_ls_restrained_S_all      1.156
_refine_ls_shift/su_max          0.020
_refine_ls_shift/su_mean         0.001

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.08388(13) 1.4438(4) 0.27299(15) 0.0281(5) Uani 1 1 d . . .
F2 F 0.05088(13) 1.2598(4) 0.47191(15) 0.0297(5) Uani 1 1 d . . .
O1 O 0.40835(15) 0.4611(4) 0.66413(15) 0.0201(4) Uani 1 1 d . . .
N1 N 0.40460(18) 0.7762(5) 0.38760(18) 0.0193(5) Uani 1 1 d . . .
H1 H 0.435(3) 0.804(8) 0.334(3) 0.026(8) Uiso 1 1 d . . .
C1 C 0.4533(2) 0.5866(6) 0.4879(2) 0.0187(5) Uani 1 1 d . . .
C2 C 0.38676(19) 0.6042(6) 0.5663(2) 0.0174(5) Uani 1 1 d . . .
C3 C 0.2965(2) 0.8183(6) 0.5022(2) 0.0184(5) Uani 1 1 d . . .
C4 C 0.2065(2) 0.9264(6) 0.5295(2) 0.0218(6) Uani 1 1 d . . .
H4 H 0.1942 0.8566 0.5997 0.026 Uiso 1 1 calc R . .
C5 C 0.1373(2) 1.1367(6) 0.4506(2) 0.0220(6) Uani 1 1 d . . .
C6 C 0.1542(2) 1.2364(6) 0.3452(2) 0.0229(6) Uani 1 1 d . . .
C7 C 0.2404(2) 1.1281(6) 0.3149(2) 0.0220(6) Uani 1 1 d . . .
H7 H 0.2502 1.1936 0.2424 0.026 Uiso 1 1 calc R . .
C8 C 0.3119(2) 0.9190(6) 0.3959(2) 0.0191(5) 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
F1 0.0263(8) 0.0249(11) 0.0309(8) 0.0048(6) 0.0103(6) 0.0074(6)
F2 0.0268(8) 0.0292(11) 0.0392(9) -0.0020(7) 0.0200(7) 0.0056(6)
O1 0.0258(9) 0.0206(11) 0.0181(8) 0.0010(6) 0.0134(7) 0.0014(7)
N1 0.0225(10) 0.0230(13) 0.0170(9) 0.0027(7) 0.0128(8) 0.0041(8)
C1 0.0214(11) 0.0220(15) 0.0156(10) -0.0001(8) 0.0107(8) -0.0015(9)
C2 0.0205(11) 0.0181(15) 0.0173(10) -0.0029(8) 0.0116(8) -0.0010(8)
C3 0.0224(11) 0.0181(15) 0.0186(10) -0.0023(9) 0.0125(8) -0.0006(9)
C4 0.0227(11) 0.0244(16) 0.0227(11) -0.0033(9) 0.0139(9) -0.0016(9)
C5 0.0190(11) 0.0213(16) 0.0285(12) -0.0046(9) 0.0129(9) 0.0000(9)
C6 0.0224(11) 0.0191(16) 0.0242(11) -0.0012(9) 0.0071(9) 0.0015(9)
C7 0.0240(11) 0.0236(16) 0.0194(10) 0.0002(9) 0.0103(9) -0.0003(9)
C8 0.0203(11) 0.0196(15) 0.0198(11) -0.0030(8) 0.0109(9) -0.0026(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
F1 C6 1.335(3) . ?
F2 C5 1.351(3) . ?
O1 C2 1.240(3) . ?
N1 C1 1.375(3) . ?
N1 C8 1.390(3) . ?
C1 C1 1.359(5) 3_666 ?
C1 C2 1.485(3) . ?
C2 C3 1.457(3) . ?
C3 C4 1.404(3) . ?
C3 C8 1.407(3) . ?
C4 C5 1.368(4) . ?
C5 C6 1.406(4) . ?
C6 C7 1.381(4) . ?
C7 C8 1.384(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
C1 N1 C8 109.47(19) . . ?
C1 C1 N1 126.1(3) 3_666 . ?
C1 C1 C2 125.6(3) 3_666 . ?
N1 C1 C2 108.3(2) . . ?
O1 C2 C3 130.4(2) . . ?
O1 C2 C1 124.8(2) . . ?
C3 C2 C1 104.80(19) . . ?
C4 C3 C8 120.7(2) . . ?
C4 C3 C2 131.9(2) . . ?
C8 C3 C2 107.4(2) . . ?
C5 C4 C3 117.2(2) . . ?
F2 C5 C4 121.2(2) . . ?
F2 C5 C6 117.3(2) . . ?
C4 C5 C6 121.4(2) . . ?
F1 C6 C7 119.5(2) . . ?
F1 C6 C5 118.1(2) . . ?
C7 C6 C5 122.3(2) . . ?
C6 C7 C8 116.3(2) . . ?
C7 C8 N1 128.0(2) . . ?
C7 C8 C3 122.0(2) . . ?
N1 C8 C3 110.0(2) . . ?

_diffrn_measured_fraction_theta_max 0.755
_diffrn_reflns_theta_full        30.55
_diffrn_measured_fraction_theta_full 0.871
_refine_diff_density_max         0.386
_refine_diff_density_min         -0.261
_refine_diff_density_rms         0.071
_database_code_depnum_ccdc_archive 'CCDC 991839'
