# Electronic Supplementary Material (ESI) for Chemical Science.
# 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_(cis-1)(trans-bpe)

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H10 Br2 F8 N4'
_chemical_formula_weight         666.18

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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   C2/c

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

_cell_length_a                   28.893(5)
_cell_length_b                   5.2362(10)
_cell_length_c                   17.648(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 118.696(2)
_cell_angle_gamma                90.00
_cell_volume                     2342.0(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    2587
_cell_measurement_theta_min      2.63
_cell_measurement_theta_max      26.66

_exptl_crystal_description       plate
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.13
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.889
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1296
_exptl_absorpt_coefficient_mu    3.548
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.3037
_exptl_absorpt_correction_T_max  0.6634
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      150(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            9467
_diffrn_reflns_av_R_equivalents  0.0319
_diffrn_reflns_av_sigmaI/netI    0.0341
_diffrn_reflns_limit_h_min       -36
_diffrn_reflns_limit_h_max       33
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         1.61
_diffrn_reflns_theta_max         27.48
_reflns_number_total             2627
_reflns_number_gt                1857
_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)+(0.0359P)²+0.0878P] 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         2627
_refine_ls_number_parameters     172
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0500
_refine_ls_R_factor_gt           0.0284
_refine_ls_wR_factor_ref         0.0710
_refine_ls_wR_factor_gt          0.0638
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_restrained_S_all      1.023
_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
Br1 Br 0.108232(11) -0.25023(5) 0.113569(16) 0.03241(10) Uani 1 1 d . . .
C1 C 0.07866(10) -0.0036(4) 0.15530(15) 0.0259(5) Uani 1 1 d . . .
C2 C 0.11076(10) 0.1627(5) 0.21991(16) 0.0280(6) Uani 1 1 d . . .
C3 C 0.08978(10) 0.3479(5) 0.24929(15) 0.0261(5) Uani 1 1 d . . .
C6 C 0.02467(9) 0.0187(4) 0.12280(14) 0.0250(5) Uani 1 1 d . . .
C4 C 0.03586(10) 0.3730(4) 0.21709(14) 0.0228(5) Uani 1 1 d . . .
C8 C 0.22272(10) 0.0182(5) 0.04299(16) 0.0291(6) Uani 1 1 d . . .
N1 N 0.16139(9) 0.3874(4) 0.06928(15) 0.0369(5) Uani 1 1 d . . .
C7 C 0.25646(11) -0.1718(5) 0.03280(17) 0.0342(6) Uani 1 1 d . . .
H7 H 0.2916 -0.1837 0.0787 0.041 Uiso 1 1 calc R . .
C9 C 0.17107(11) 0.0670(5) -0.01893(17) 0.0349(6) Uani 1 1 d . . .
H9 H 0.1555 -0.0253 -0.0718 0.042 Uiso 1 1 calc R . .
C5 C 0.00338(10) 0.2028(4) 0.15303(15) 0.0242(6) Uani 1 1 d . . .
C12 C 0.21095(12) 0.3406(5) 0.12794(18) 0.0390(7) Uani 1 1 d . . .
H12 H 0.2255 0.4367 0.1800 0.047 Uiso 1 1 calc R . .
C13 C 0.24246(11) 0.1622(5) 0.11823(18) 0.0362(7) Uani 1 1 d . . .
H13 H 0.2777 0.1371 0.1628 0.043 Uiso 1 1 calc R . .
C10 C 0.14243(12) 0.2501(5) -0.00349(19) 0.0374(6) Uani 1 1 d . . .
H10 H 0.1072 0.2808 -0.0470 0.045 Uiso 1 1 calc R . .
N2 N 0.01724(8) 0.6014(4) 0.23844(13) 0.0278(5) Uani 1 1 d . . .
F1 F -0.00829(6) -0.1448(3) 0.06202(9) 0.0350(4) Uani 1 1 d . . .
F4 F 0.12202(6) 0.5158(3) 0.30972(9) 0.0373(4) Uani 1 1 d . . .
F3 F 0.16342(6) 0.1479(3) 0.25436(9) 0.0404(4) Uani 1 1 d . . .
F2 F -0.04926(6) 0.2221(3) 0.11775(9) 0.0328(3) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C1 1.883(2) . ?
C1 C2 1.380(3) . ?
C1 C6 1.385(3) . ?
C2 F3 1.343(3) . ?
C2 C3 1.370(4) . ?
C3 F4 1.351(3) . ?
C3 C4 1.384(3) . ?
C6 F1 1.345(3) . ?
C6 C5 1.381(3) . ?
C4 C5 1.391(3) . ?
C4 N2 1.434(3) . ?
C8 C9 1.386(4) . ?
C8 C13 1.389(3) . ?
C8 C7 1.463(3) . ?
N1 C12 1.326(4) . ?
N1 C10 1.338(3) . ?
C7 C7 1.317(5) 7_545 ?
C9 C10 1.377(3) . ?
C5 F2 1.342(3) . ?
C12 C13 1.371(4) . ?
N2 N2 1.245(4) 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
C2 C1 C6 117.8(2) . . ?
C2 C1 Br1 120.33(19) . . ?
C6 C1 Br1 121.91(18) . . ?
F3 C2 C3 118.7(2) . . ?
F3 C2 C1 120.2(2) . . ?
C3 C2 C1 121.0(2) . . ?
F4 C3 C2 119.8(2) . . ?
F4 C3 C4 118.4(2) . . ?
C2 C3 C4 121.8(2) . . ?
F1 C6 C5 118.4(2) . . ?
F1 C6 C1 120.1(2) . . ?
C5 C6 C1 121.4(2) . . ?
C3 C4 C5 117.4(2) . . ?
C3 C4 N2 117.5(2) . . ?
C5 C4 N2 123.8(2) . . ?
C9 C8 C13 116.5(2) . . ?
C9 C8 C7 123.9(2) . . ?
C13 C8 C7 119.7(2) . . ?
C12 N1 C10 116.2(2) . . ?
C7 C7 C8 127.3(3) 7_545 . ?
C10 C9 C8 119.6(2) . . ?
F2 C5 C6 119.3(2) . . ?
F2 C5 C4 120.1(2) . . ?
C6 C5 C4 120.6(2) . . ?
N1 C12 C13 124.1(3) . . ?
C12 C13 C8 119.8(3) . . ?
N1 C10 C9 123.8(3) . . ?
N2 N2 C4 123.13(12) 2 . ?

_diffrn_measured_fraction_theta_max 0.979
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.373
_refine_diff_density_min         -0.334
_refine_diff_density_rms         0.067
_database_code_depnum_ccdc_archive 'CCDC 984291'
#######################################################################
#
#                 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_(cis-1)(trans-ape)

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            cis-dibromooctafluoroazobenzene:azopyridine
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 N2 Br2 F8, C10 H8 N4'
_chemical_formula_sum            'C22 H8 Br2 F8 N6'
_chemical_formula_weight         668.16

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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   C2/c

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

_cell_length_a                   36.953(4)
_cell_length_b                   5.2778(6)
_cell_length_c                   11.5441(12)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.5290(10)
_cell_angle_gamma                90.00
_cell_volume                     2251.3(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    4212
_cell_measurement_theta_min      3.31
_cell_measurement_theta_max      25.94

_exptl_crystal_description       Plate
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.62
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.11
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.971
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1296
_exptl_absorpt_coefficient_mu    3.693
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.2061
_exptl_absorpt_correction_T_max  0.6782
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      150(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            11741
_diffrn_reflns_av_R_equivalents  0.0328
_diffrn_reflns_av_sigmaI/netI    0.0262
_diffrn_reflns_limit_h_min       -46
_diffrn_reflns_limit_h_max       46
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.20
_diffrn_reflns_theta_max         26.73
_reflns_number_total             2385
_reflns_number_gt                1950
_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)+(0.0325P)²+2.3945P] 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         2385
_refine_ls_number_parameters     172
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0378
_refine_ls_R_factor_gt           0.0270
_refine_ls_wR_factor_ref         0.0700
_refine_ls_wR_factor_gt          0.0651
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_restrained_S_all      1.051
_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 0.40664(7) 0.7851(5) 0.2876(2) 0.0371(5) Uani 1 1 d . . .
C2 C 0.40948(6) 0.9462(5) 0.1943(2) 0.0340(5) Uani 1 1 d . . .
C3 C 0.43923(6) 0.9193(5) 0.1232(2) 0.0349(5) Uani 1 1 d . . .
C4 C 0.46501(7) 0.7376(5) 0.1447(2) 0.0361(6) Uani 1 1 d . . .
C5 C 0.46212(6) 0.5736(5) 0.2377(2) 0.0368(6) Uani 1 1 d . . .
C6 C 0.43204(7) 0.6010(5) 0.3083(2) 0.0396(6) Uani 1 1 d . . .
C7 C 0.32694(8) 0.6936(6) -0.0055(3) 0.0522(7) Uani 1 1 d . . .
H7 H 0.3441 0.6185 -0.0559 0.063 Uiso 1 1 calc R . .
C8 C 0.30656(8) 0.8891(6) -0.0474(3) 0.0533(7) Uani 1 1 d . . .
H8 H 0.3096 0.9477 -0.1245 0.064 Uiso 1 1 calc R . .
C9 C 0.28157(7) 0.9995(5) 0.0238(3) 0.0454(7) Uani 1 1 d . . .
C10 C 0.27829(7) 0.9088(6) 0.1357(3) 0.0488(7) Uani 1 1 d . . .
H10 H 0.2614 0.9813 0.1876 0.059 Uiso 1 1 calc R . .
C11 C 0.30016(8) 0.7109(6) 0.1697(3) 0.0476(7) Uani 1 1 d . . .
H11 H 0.2978 0.6487 0.2465 0.057 Uiso 1 1 calc R . .
N1 N 0.32444(6) 0.6012(5) 0.1015(2) 0.0467(5) Uani 1 1 d . . .
N2 N 0.26065(7) 1.2083(5) -0.0339(2) 0.0558(6) Uani 1 1 d . . .
N3 N 0.48307(6) 0.3466(4) 0.2494(2) 0.0481(6) Uani 1 1 d . . .
Br1 Br 0.374601(7) 1.19728(5) 0.16376(2) 0.04067(10) Uani 1 1 d . . .
F1 F 0.37805(4) 0.8029(4) 0.35810(14) 0.0580(5) Uani 1 1 d . . .
F2 F 0.44328(4) 1.0729(3) 0.03204(13) 0.0539(4) Uani 1 1 d . . .
F3 F 0.49270(4) 0.7143(3) 0.07112(15) 0.0533(4) Uani 1 1 d . . .
F4 F 0.42756(4) 0.4406(3) 0.39714(14) 0.0597(5) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 F1 1.343(3) . ?
C1 C6 1.371(4) . ?
C1 C2 1.377(3) . ?
C2 C3 1.386(3) . ?
C2 Br1 1.879(2) . ?
C3 F2 1.337(3) . ?
C3 C4 1.373(4) . ?
C4 F3 1.342(3) . ?
C4 C5 1.384(4) . ?
C5 C6 1.392(4) . ?
C5 N3 1.432(3) . ?
C6 F4 1.341(3) . ?
C7 N1 1.332(4) . ?
C7 C8 1.363(4) . ?
C8 C9 1.372(4) . ?
C9 C10 1.383(4) . ?
C9 N2 1.498(4) . ?
C10 C11 1.376(4) . ?
C11 N1 1.331(4) . ?
N2 N2 1.198(5) 7_575 ?
N3 N3 1.251(5) 2_655 ?

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
F1 C1 C6 119.0(2) . . ?
F1 C1 C2 119.8(2) . . ?
C6 C1 C2 121.2(2) . . ?
C1 C2 C3 117.8(2) . . ?
C1 C2 Br1 121.66(19) . . ?
C3 C2 Br1 120.50(19) . . ?
F2 C3 C4 118.9(2) . . ?
F2 C3 C2 120.0(2) . . ?
C4 C3 C2 121.1(2) . . ?
F3 C4 C3 118.8(2) . . ?
F3 C4 C5 119.9(2) . . ?
C3 C4 C5 121.3(2) . . ?
C4 C5 C6 117.2(2) . . ?
C4 C5 N3 123.4(2) . . ?
C6 C5 N3 117.8(2) . . ?
F4 C6 C1 119.5(2) . . ?
F4 C6 C5 119.1(2) . . ?
C1 C6 C5 121.4(2) . . ?
N1 C7 C8 124.3(3) . . ?
C7 C8 C9 118.8(3) . . ?
C8 C9 C10 118.5(3) . . ?
C8 C9 N2 113.2(3) . . ?
C10 C9 N2 128.3(3) . . ?
C11 C10 C9 118.2(3) . . ?
N1 C11 C10 124.0(3) . . ?
C11 N1 C7 116.2(2) . . ?
N2 N2 C9 108.6(3) 7_575 . ?
N3 N3 C5 122.74(14) 2_655 . ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.639
_refine_diff_density_min         -0.351
_refine_diff_density_rms         0.058
_database_code_depnum_ccdc_archive 'CCDC 984292'
#######################################################################
#
#                 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_(cis-2)(trans-bpe)

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H10 F8 I2 N4'
_chemical_formula_weight         760.16

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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   C2/c

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

_cell_length_a                   29.154(5)
_cell_length_b                   5.2244(9)
_cell_length_c                   18.283(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 120.726(2)
_cell_angle_gamma                90.00
_cell_volume                     2393.8(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    3240
_cell_measurement_theta_min      2.95
_cell_measurement_theta_max      27.28

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.06
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.109
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1440
_exptl_absorpt_coefficient_mu    2.712
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5390
_exptl_absorpt_correction_T_max  0.8542
_exptl_absorpt_process_details   SADABS

_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  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9638
_diffrn_reflns_av_R_equivalents  0.0337
_diffrn_reflns_av_sigmaI/netI    0.0341
_diffrn_reflns_limit_h_min       -37
_diffrn_reflns_limit_h_max       37
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         1.63
_diffrn_reflns_theta_max         28.28
_reflns_number_total             2729
_reflns_number_gt                2198
_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)+(0.0259P)²+3.3965P] 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         2729
_refine_ls_number_parameters     172
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0397
_refine_ls_R_factor_gt           0.0263
_refine_ls_wR_factor_ref         0.0602
_refine_ls_wR_factor_gt          0.0551
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_restrained_S_all      1.025
_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
I1 I 0.111380(8) 1.26529(4) 0.110433(13) 0.01907(7) Uani 1 1 d . . .
F1 F -0.01060(7) 1.1422(4) 0.06353(12) 0.0234(4) Uani 1 1 d . . .
F2 F 0.12300(7) 0.4853(4) 0.31181(12) 0.0255(4) Uani 1 1 d . . .
F3 F 0.16399(7) 0.8462(4) 0.25720(12) 0.0255(4) Uani 1 1 d . . .
F4 F -0.05098(7) 0.7834(3) 0.11990(12) 0.0224(4) Uani 1 1 d . . .
N1 N 0.01733(11) 0.4010(5) 0.23925(17) 0.0197(6) Uani 1 1 d . . .
N2 N 0.83615(11) 0.6057(5) 0.43382(18) 0.0210(6) Uani 1 1 d . . .
C10 C 0.82757(13) 0.9201(6) 0.5215(2) 0.0201(7) Uani 1 1 d . . .
H10 H 0.8432 1.0040 0.5751 0.024 Uiso 1 1 calc R . .
C1 C 0.07788(13) 1.0023(6) 0.15743(19) 0.0164(7) Uani 1 1 d . . .
C2 C 0.02338(12) 0.9810(6) 0.12525(19) 0.0171(7) Uani 1 1 d . . .
C3 C 0.00223(12) 0.8002(6) 0.1549(2) 0.0165(6) Uani 1 1 d . . .
C4 C 0.03560(12) 0.6305(6) 0.2193(2) 0.0157(6) Uani 1 1 d . . .
C5 C 0.08990(13) 0.6520(6) 0.2513(2) 0.0183(7) Uani 1 1 d . . .
C6 C 0.11051(12) 0.8360(6) 0.2224(2) 0.0180(7) Uani 1 1 d . . .
C7 C 0.78695(14) 0.6661(6) 0.3723(2) 0.0247(8) Uani 1 1 d . . .
H7 H 0.7723 0.5771 0.3198 0.030 Uiso 1 1 calc R . .
C8 C 0.75591(13) 0.8509(6) 0.3805(2) 0.0229(7) Uani 1 1 d . . .
H8 H 0.7211 0.8868 0.3344 0.028 Uiso 1 1 calc R . .
C9 C 0.77619(13) 0.9843(6) 0.4570(2) 0.0177(7) Uani 1 1 d . . .
C12 C 0.74316(13) 1.1817(6) 0.4655(2) 0.0213(7) Uani 1 1 d . . .
H12 H 0.7090 1.2138 0.4171 0.026 Uiso 1 1 calc R . .
C11 C 0.85562(13) 0.7337(6) 0.5072(2) 0.0229(7) Uani 1 1 d . . .
H11 H 0.8907 0.6941 0.5518 0.027 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I1 C1 2.106(3) . ?
F1 C2 1.350(3) . ?
F2 C5 1.350(3) . ?
F3 C6 1.351(3) . ?
F4 C3 1.345(3) . ?
N1 N1 1.257(5) 2 ?
N1 C4 1.433(4) . ?
N2 C7 1.332(4) . ?
N2 C11 1.338(4) . ?
C10 C11 1.380(4) . ?
C10 C9 1.394(4) . ?
C1 C6 1.384(4) . ?
C1 C2 1.389(4) . ?
C2 C3 1.381(4) . ?
C3 C4 1.396(4) . ?
C4 C5 1.384(4) . ?
C5 C6 1.375(5) . ?
C7 C8 1.383(5) . ?
C8 C9 1.395(4) . ?
C9 C12 1.473(4) . ?
C12 C12 1.322(6) 7_676 ?

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 N1 C4 122.84(16) 2 . ?
C7 N2 C11 116.8(3) . . ?
C11 C10 C9 119.6(3) . . ?
C6 C1 C2 116.7(3) . . ?
C6 C1 I1 120.1(2) . . ?
C2 C1 I1 123.2(2) . . ?
F1 C2 C3 118.1(3) . . ?
F1 C2 C1 119.8(3) . . ?
C3 C2 C1 122.1(3) . . ?
F4 C3 C2 119.7(3) . . ?
F4 C3 C4 119.8(3) . . ?
C2 C3 C4 120.5(3) . . ?
C5 C4 C3 117.3(3) . . ?
C5 C4 N1 117.0(3) . . ?
C3 C4 N1 123.8(3) . . ?
F2 C5 C6 119.8(3) . . ?
F2 C5 C4 118.6(3) . . ?
C6 C5 C4 121.6(3) . . ?
F3 C6 C5 118.2(3) . . ?
F3 C6 C1 120.1(3) . . ?
C5 C6 C1 121.7(3) . . ?
N2 C7 C8 123.8(3) . . ?
C7 C8 C9 119.4(3) . . ?
C10 C9 C8 116.8(3) . . ?
C10 C9 C12 123.8(3) . . ?
C8 C9 C12 119.4(3) . . ?
C12 C12 C9 125.8(4) 7_676 . ?
N2 C11 C10 123.6(3) . . ?

_diffrn_measured_fraction_theta_max 0.923
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         1.280
_refine_diff_density_min         -0.554
_refine_diff_density_rms         0.108
_database_code_depnum_ccdc_archive 'CCDC 984293'
#######################################################################
#
#                 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_(cis-2)(trans-ape)

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H8 F8 I2 N6'
_chemical_formula_weight         762.14

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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   C2/c

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

_cell_length_a                   28.722(4)
_cell_length_b                   5.1901(7)
_cell_length_c                   18.220(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 120.6230(10)
_cell_angle_gamma                90.00
_cell_volume                     2337.2(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    5971
_cell_measurement_theta_min      2.26
_cell_measurement_theta_max      28.04

_exptl_crystal_description       needle
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.166
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1440
_exptl_absorpt_coefficient_mu    2.781
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.3702
_exptl_absorpt_correction_T_max  0.8781
_exptl_absorpt_process_details   SADABS

_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  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12549
_diffrn_reflns_av_R_equivalents  0.0267
_diffrn_reflns_av_sigmaI/netI    0.0225
_diffrn_reflns_limit_h_min       -38
_diffrn_reflns_limit_h_max       37
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         1.65
_diffrn_reflns_theta_max         28.28
_reflns_number_total             2737
_reflns_number_gt                2428
_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)+(0.0191P)²+6.7143P] 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         2737
_refine_ls_number_parameters     172
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0266
_refine_ls_R_factor_gt           0.0214
_refine_ls_wR_factor_ref         0.0498
_refine_ls_wR_factor_gt          0.0476
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_restrained_S_all      1.042
_refine_ls_shift/su_max          0.007
_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
I1 I 0.887595(7) 0.77797(3) 0.391248(10) 0.01986(6) Uani 1 1 d . . .
F1 F 0.87498(6) -0.0015(3) 0.18672(10) 0.0277(4) Uani 1 1 d . . .
F2 F 0.83357(6) 0.3615(3) 0.24255(10) 0.0279(4) Uani 1 1 d . . .
F3 F 1.01081(6) 0.6526(3) 0.43797(9) 0.0254(3) Uani 1 1 d . . .
F4 F 1.05146(6) 0.2909(3) 0.38073(10) 0.0236(3) Uani 1 1 d . . .
N1 N 0.98224(9) -0.0893(4) 0.26013(14) 0.0208(4) Uani 1 1 d . . .
N2 N 0.66561(9) 0.6232(4) 0.06181(15) 0.0232(5) Uani 1 1 d . . .
N3 N 0.75940(10) 1.2039(5) 0.03588(15) 0.0266(5) Uani 1 1 d . . .
C1 C 0.92094(10) 0.5147(5) 0.34268(16) 0.0184(5) Uani 1 1 d . . .
C2 C 0.88747(10) 0.3510(5) 0.27705(16) 0.0194(5) Uani 1 1 d . . .
C3 C 0.90829(10) 0.1640(5) 0.24736(16) 0.0188(5) Uani 1 1 d . . .
C4 C 0.96361(10) 0.1416(5) 0.28053(15) 0.0170(5) Uani 1 1 d . . .
C5 C 0.99750(10) 0.3102(5) 0.34535(16) 0.0174(5) Uani 1 1 d . . .
C6 C 0.97625(10) 0.4926(5) 0.37552(15) 0.0181(5) Uani 1 1 d . . .
C7 C 0.71515(11) 0.6900(5) 0.12459(18) 0.0257(6) Uani 1 1 d . . .
H7 H 0.7299 0.6009 0.1774 0.031 Uiso 1 1 calc R . .
C8 C 0.74578(11) 0.8798(6) 0.11703(18) 0.0274(6) Uani 1 1 d . . .
H8 H 0.7805 0.9230 0.1637 0.033 Uiso 1 1 calc R . .
C9 C 0.72482(11) 1.0072(5) 0.03949(18) 0.0226(5) Uani 1 1 d . . .
C10 C 0.64593(11) 0.7479(5) -0.01236(17) 0.0237(5) Uani 1 1 d . . .
H10 H 0.6109 0.7027 -0.0576 0.028 Uiso 1 1 calc R . .
C11 C 0.67394(11) 0.9402(5) -0.02689(17) 0.0237(6) Uani 1 1 d . . .
H11 H 0.6587 1.0233 -0.0808 0.028 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I1 C1 2.105(2) . ?
F1 C3 1.340(3) . ?
F2 C2 1.343(3) . ?
F3 C6 1.349(3) . ?
F4 C5 1.345(3) . ?
N1 N1 1.249(4) 2_755 ?
N1 C4 1.436(3) . ?
N2 C10 1.337(4) . ?
N2 C7 1.340(4) . ?
N3 N3 1.229(5) 7_675 ?
N3 C9 1.449(3) . ?
C1 C2 1.380(4) . ?
C1 C6 1.388(4) . ?
C2 C3 1.387(4) . ?
C3 C4 1.387(4) . ?
C4 C5 1.392(3) . ?
C5 C6 1.383(3) . ?
C7 C8 1.374(4) . ?
C8 C9 1.389(4) . ?
C9 C11 1.385(4) . ?
C10 C11 1.389(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
N1 N1 C4 122.97(13) 2_755 . ?
C10 N2 C7 117.1(2) . . ?
N3 N3 C9 112.5(3) 7_675 . ?
C2 C1 C6 117.5(2) . . ?
C2 C1 I1 119.90(18) . . ?
C6 C1 I1 122.58(19) . . ?
F2 C2 C1 120.6(2) . . ?
F2 C2 C3 118.0(2) . . ?
C1 C2 C3 121.4(2) . . ?
F1 C3 C2 120.1(2) . . ?
F1 C3 C4 118.9(2) . . ?
C2 C3 C4 121.0(2) . . ?
C3 C4 C5 117.9(2) . . ?
C3 C4 N1 116.9(2) . . ?
C5 C4 N1 123.5(2) . . ?
F4 C5 C6 119.6(2) . . ?
F4 C5 C4 119.8(2) . . ?
C6 C5 C4 120.5(2) . . ?
F3 C6 C5 118.2(2) . . ?
F3 C6 C1 120.1(2) . . ?
C5 C6 C1 121.7(2) . . ?
N2 C7 C8 123.8(3) . . ?
C7 C8 C9 118.4(3) . . ?
C11 C9 C8 119.1(2) . . ?
C11 C9 N3 125.4(2) . . ?
C8 C9 N3 115.4(2) . . ?
N2 C10 C11 123.6(3) . . ?
C9 C11 C10 118.0(2) . . ?

_diffrn_measured_fraction_theta_max 0.946
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.871
_refine_diff_density_min         -0.363
_refine_diff_density_rms         0.090
_database_code_depnum_ccdc_archive 'CCDC 984294'
#######################################################################
#
#                 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_(cis-2)(cis-bpe)

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H10 F8 I2 N4'
_chemical_formula_weight         760.16

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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   C2/c

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

_cell_length_a                   40.225(5)
_cell_length_b                   5.8436(7)
_cell_length_c                   25.726(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 123.6470(10)
_cell_angle_gamma                90.00
_cell_volume                     5033.9(10)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    6173
_cell_measurement_theta_min      2.43
_cell_measurement_theta_max      27.87

_exptl_crystal_description       Needle
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.80
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.006
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2880
_exptl_absorpt_coefficient_mu    2.580
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.2336
_exptl_absorpt_correction_T_max  0.7788
_exptl_absorpt_process_details   SADABS

_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  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            17313
_diffrn_reflns_av_R_equivalents  0.0344
_diffrn_reflns_av_sigmaI/netI    0.0383
_diffrn_reflns_limit_h_min       -52
_diffrn_reflns_limit_h_max       51
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_theta_min         1.22
_diffrn_reflns_theta_max         27.48
_reflns_number_total             5644
_reflns_number_gt                4606
_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)+(0.0238P)²+10.3501P] 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         5644
_refine_ls_number_parameters     343
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0389
_refine_ls_R_factor_gt           0.0277
_refine_ls_wR_factor_ref         0.0656
_refine_ls_wR_factor_gt          0.0580
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_restrained_S_all      1.039
_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
I2 I 0.228762(6) 0.05657(4) 0.377645(10) 0.02017(6) Uani 1 1 d . . .
I1 I 0.002226(7) -0.15044(4) 0.388323(12) 0.02847(7) Uani 1 1 d . . .
F5 F 0.17661(6) 0.5096(3) 0.31277(9) 0.0271(5) Uani 1 1 d . . .
F6 F 0.13906(6) 0.7985(3) 0.34507(10) 0.0304(5) Uani 1 1 d . . .
F4 F 0.02407(6) 0.1735(4) 0.31132(10) 0.0416(6) Uani 1 1 d . . .
F1 F 0.06420(7) 0.0960(4) 0.52122(10) 0.0372(6) Uani 1 1 d . . .
F2 F 0.11303(6) 0.4567(4) 0.55196(9) 0.0340(5) Uani 1 1 d . . .
F3 F 0.07191(6) 0.5343(4) 0.34220(10) 0.0354(5) Uani 1 1 d . . .
F7 F 0.17307(5) 0.3291(4) 0.51667(9) 0.0259(5) Uani 1 1 d . . .
F8 F 0.21289(5) 0.0476(3) 0.48732(9) 0.0241(4) Uani 1 1 d . . .
N3 N 0.94747(9) 0.5001(6) 0.34656(15) 0.0318(8) Uani 1 1 d . . .
C20 C 0.82130(9) 0.0276(6) 0.32184(15) 0.0195(7) Uani 1 1 d . . .
N4 N 0.77613(8) 0.2986(5) 0.35107(14) 0.0237(6) Uani 1 1 d . . .
C19 C 0.80662(9) 0.2388(6) 0.29421(15) 0.0203(7) Uani 1 1 d . . .
H4 H 0.8119 0.2962 0.2649 0.024 Uiso 1 1 calc R . .
N1 N 0.14093(8) 0.7516(5) 0.45263(14) 0.0266(7) Uani 1 1 d . . .
N2 N 0.11536(8) 0.7126(5) 0.46484(14) 0.0265(7) Uani 1 1 d . . .
C13 C 0.93310(11) 0.4358(7) 0.38026(18) 0.0295(8) Uani 1 1 d . . .
H1 H 0.9413 0.5183 0.4174 0.035 Uiso 1 1 calc R . .
C14 C 0.90691(10) 0.2558(7) 0.36402(16) 0.0254(8) Uani 1 1 d . . .
H2 H 0.8972 0.2183 0.3893 0.030 Uiso 1 1 calc R . .
C15 C 0.89473(9) 0.1293(6) 0.31042(16) 0.0218(7) Uani 1 1 d . . .
C23 C 0.87091(10) -0.0799(6) 0.29437(16) 0.0241(8) Uani 1 1 d . . .
H4A H 0.8769 -0.1972 0.2752 0.029 Uiso 1 1 calc R . .
C24 C 0.84202(11) -0.1273(6) 0.30311(17) 0.0257(8) Uani 1 1 d . . .
H5 H 0.8335 -0.2823 0.2964 0.031 Uiso 1 1 calc R . .
C21 C 0.81282(11) -0.0440(6) 0.36523(16) 0.0250(8) Uani 1 1 d . . .
H6 H 0.8222 -0.1878 0.3855 0.030 Uiso 1 1 calc R . .
C22 C 0.79059(11) 0.0964(6) 0.37844(17) 0.0274(8) Uani 1 1 d . . .
H7 H 0.7854 0.0460 0.4084 0.033 Uiso 1 1 calc R . .
C18 C 0.78432(10) 0.3655(6) 0.30953(16) 0.0238(7) Uani 1 1 d . . .
H8 H 0.7741 0.5089 0.2894 0.029 Uiso 1 1 calc R . .
C16 C 0.90973(10) 0.1988(7) 0.27524(16) 0.0266(8) Uani 1 1 d . . .
H9 H 0.9022 0.1192 0.2380 0.032 Uiso 1 1 calc R . .
C17 C 0.93546(11) 0.3828(7) 0.29433(18) 0.0303(9) Uani 1 1 d . . .
H10 H 0.9450 0.4278 0.2694 0.036 Uiso 1 1 calc R . .
C7 C 0.19580(9) 0.2695(6) 0.39904(15) 0.0193(7) Uani 1 1 d . . .
C8 C 0.17639(10) 0.4627(6) 0.36396(16) 0.0212(7) Uani 1 1 d . . .
C9 C 0.15702(10) 0.6123(6) 0.38003(16) 0.0217(7) Uani 1 1 d . . .
C10 C 0.15532(9) 0.5701(6) 0.43152(16) 0.0205(7) Uani 1 1 d . . .
C4 C 0.09441(10) 0.4983(6) 0.44811(16) 0.0217(7) Uani 1 1 d . . .
C3 C 0.09067(10) 0.3845(6) 0.49218(15) 0.0225(8) Uani 1 1 d . . .
C2 C 0.06580(10) 0.2011(7) 0.47605(17) 0.0263(8) Uani 1 1 d . . .
C1 C 0.04241(10) 0.1229(6) 0.41508(17) 0.0250(8) Uani 1 1 d . . .
C5 C 0.07126(10) 0.4208(6) 0.38723(16) 0.0238(8) Uani 1 1 d . . .
C6 C 0.04593(10) 0.2377(7) 0.37136(16) 0.0278(8) Uani 1 1 d . . .
C11 C 0.17366(9) 0.3744(6) 0.46590(16) 0.0213(7) Uani 1 1 d . . .
C12 C 0.19411(9) 0.2290(6) 0.45055(15) 0.0194(7) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I2 C7 2.102(3) . ?
I1 C1 2.099(4) . ?
F5 C8 1.350(4) . ?
F6 C9 1.340(4) . ?
F4 C6 1.340(4) . ?
F1 C2 1.347(4) . ?
F2 C3 1.349(4) . ?
F3 C5 1.348(4) . ?
F7 C11 1.346(4) . ?
F8 C12 1.341(4) . ?
N3 C13 1.335(5) . ?
N3 C17 1.338(5) . ?
C20 C19 1.383(5) . ?
C20 C21 1.400(4) . ?
C20 C24 1.480(5) . ?
N4 C22 1.333(5) . ?
N4 C18 1.339(4) . ?
C19 C18 1.378(5) . ?
N1 N2 1.252(4) . ?
N1 C10 1.450(4) . ?
N2 C4 1.436(5) . ?
C13 C14 1.380(5) . ?
C14 C15 1.393(5) . ?
C15 C16 1.398(5) . ?
C15 C23 1.465(5) . ?
C23 C24 1.329(5) . ?
C21 C22 1.388(5) . ?
C16 C17 1.380(5) . ?
C7 C12 1.385(4) . ?
C7 C8 1.385(5) . ?
C8 C9 1.378(5) . ?
C9 C10 1.386(5) . ?
C10 C11 1.383(5) . ?
C4 C5 1.382(5) . ?
C4 C3 1.392(5) . ?
C3 C2 1.365(5) . ?
C2 C1 1.385(5) . ?
C1 C6 1.382(5) . ?
C5 C6 1.374(5) . ?
C11 C12 1.384(5) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C13 N3 C17 117.6(3) . . ?
C19 C20 C21 117.0(3) . . ?
C19 C20 C24 122.4(3) . . ?
C21 C20 C24 120.4(3) . . ?
C22 N4 C18 116.9(3) . . ?
C18 C19 C20 119.5(3) . . ?
N2 N1 C10 121.0(3) . . ?
N1 N2 C4 120.7(3) . . ?
N3 C13 C14 123.4(3) . . ?
C13 C14 C15 119.7(3) . . ?
C14 C15 C16 116.5(3) . . ?
C14 C15 C23 122.6(3) . . ?
C16 C15 C23 120.6(3) . . ?
C24 C23 C15 128.5(3) . . ?
C23 C24 C20 129.1(3) . . ?
C22 C21 C20 119.6(3) . . ?
N4 C22 C21 123.2(3) . . ?
N4 C18 C19 123.9(3) . . ?
C17 C16 C15 120.2(3) . . ?
N3 C17 C16 122.6(3) . . ?
C12 C7 C8 117.0(3) . . ?
C12 C7 I2 121.5(3) . . ?
C8 C7 I2 121.4(2) . . ?
F5 C8 C9 118.3(3) . . ?
F5 C8 C7 119.7(3) . . ?
C9 C8 C7 122.0(3) . . ?
F6 C9 C8 119.9(3) . . ?
F6 C9 C10 119.5(3) . . ?
C8 C9 C10 120.6(3) . . ?
C11 C10 C9 117.9(3) . . ?
C11 C10 N1 123.2(3) . . ?
C9 C10 N1 118.0(3) . . ?
C5 C4 C3 117.2(3) . . ?
C5 C4 N2 122.7(3) . . ?
C3 C4 N2 118.9(3) . . ?
F2 C3 C2 120.4(3) . . ?
F2 C3 C4 118.3(3) . . ?
C2 C3 C4 121.3(3) . . ?
F1 C2 C3 118.2(3) . . ?
F1 C2 C1 120.0(3) . . ?
C3 C2 C1 121.8(3) . . ?
C6 C1 C2 116.7(3) . . ?
C6 C1 I1 120.7(3) . . ?
C2 C1 I1 122.6(3) . . ?
F3 C5 C6 119.5(3) . . ?
F3 C5 C4 119.4(3) . . ?
C6 C5 C4 121.0(3) . . ?
F4 C6 C5 117.7(3) . . ?
F4 C6 C1 120.3(3) . . ?
C5 C6 C1 122.0(3) . . ?
F7 C11 C10 119.6(3) . . ?
F7 C11 C12 119.3(3) . . ?
C10 C11 C12 121.1(3) . . ?
F8 C12 C11 118.4(3) . . ?
F8 C12 C7 120.2(3) . . ?
C11 C12 C7 121.4(3) . . ?

_diffrn_measured_fraction_theta_max 0.975
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         1.305
_refine_diff_density_min         -0.563
_refine_diff_density_rms         0.114
_database_code_depnum_ccdc_archive 'CCDC 984295'
#######################################################################
#
#                 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_(trans-1)(trans-bpe)

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H10 Br2 F8 N4'
_chemical_formula_weight         666.18

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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

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

_cell_length_a                   6.0828(11)
_cell_length_b                   8.3133(15)
_cell_length_c                   12.157(2)
_cell_angle_alpha                70.137(2)
_cell_angle_beta                 84.722(2)
_cell_angle_gamma                79.999(2)
_cell_volume                     569.04(18)
_cell_formula_units_Z            1
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    2702
_cell_measurement_theta_min      2.64
_cell_measurement_theta_max      27.31

_exptl_crystal_description       plate
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.04
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.944
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             324
_exptl_absorpt_coefficient_mu    3.650
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4280
_exptl_absorpt_correction_T_max  0.8677
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      150(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            4568
_diffrn_reflns_av_R_equivalents  0.0194
_diffrn_reflns_av_sigmaI/netI    0.0295
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.78
_diffrn_reflns_theta_max         26.37
_reflns_number_total             2302
_reflns_number_gt                2088
_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)+(0.0267P)²+0.3035P] 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         2302
_refine_ls_number_parameters     172
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0286
_refine_ls_R_factor_gt           0.0238
_refine_ls_wR_factor_ref         0.0578
_refine_ls_wR_factor_gt          0.0561
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_restrained_S_all      1.043
_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
Br1 Br 0.30114(4) 0.69017(3) 0.26696(2) 0.02415(8) Uani 1 1 d . . .
F4 F 0.7823(2) 0.60972(16) 0.18349(12) 0.0286(3) Uani 1 1 d . . .
F1 F 0.2661(2) 0.36456(17) 0.48233(12) 0.0289(3) Uani 1 1 d . . .
F2 F 0.5658(2) 0.08808(16) 0.56873(11) 0.0275(3) Uani 1 1 d . . .
F3 F 1.0888(2) 0.33300(17) 0.27051(12) 0.0287(3) Uani 1 1 d . . .
N1 N 0.0076(3) 1.0136(2) 0.82788(18) 0.0283(5) Uani 1 1 d . . .
C1 C 0.3374(4) 0.7244(3) 0.9159(2) 0.0223(5) Uani 1 1 d . . .
N2 N 1.0234(3) 0.0651(2) 0.45909(18) 0.0268(4) Uani 1 1 d . . .
C8 C 0.4689(4) 0.3570(3) 0.4280(2) 0.0223(5) Uani 1 1 d . . .
C11 C 0.8870(4) 0.3392(3) 0.3242(2) 0.0217(5) Uani 1 1 d . . .
C7 C 0.5152(4) 0.4935(3) 0.3301(2) 0.0208(5) Uani 1 1 d . . .
C3 C 0.2149(4) 1.0079(3) 0.7812(2) 0.0289(5) Uani 1 1 d . . .
H3 H 0.2490 1.1044 0.7167 0.035 Uiso 1 1 calc R . .
C4 C -0.0346(4) 0.8761(3) 0.9191(2) 0.0286(5) Uani 1 1 d . . .
H4 H -0.1806 0.8784 0.9544 0.034 Uiso 1 1 calc R . .
C6 C 0.5124(4) 0.5742(3) 0.9579(2) 0.0248(5) Uani 1 1 d . . .
H6 H 0.6568 0.5839 0.9214 0.030 Uiso 1 1 calc R . .
C2 C 0.3836(4) 0.8688(3) 0.8218(2) 0.0266(5) Uani 1 1 d . . .
H2 H 0.5291 0.8718 0.7860 0.032 Uiso 1 1 calc R . .
C9 C 0.6262(4) 0.2133(3) 0.47318(19) 0.0217(5) Uani 1 1 d . . .
C5 C 0.1217(4) 0.7306(3) 0.9651(2) 0.0261(5) Uani 1 1 d . . .
H5 H 0.0821 0.6361 1.0296 0.031 Uiso 1 1 calc R . .
C10 C 0.8413(4) 0.1999(3) 0.4227(2) 0.0225(5) Uani 1 1 d . . .
C12 C 0.7279(4) 0.4813(3) 0.27909(19) 0.0225(5) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C7 1.884(2) . ?
F4 C12 1.345(2) . ?
F1 C8 1.347(3) . ?
F2 C9 1.342(2) . ?
F3 C11 1.338(3) . ?
N1 C4 1.338(3) . ?
N1 C3 1.334(3) . ?
C1 C2 1.398(3) . ?
C1 C5 1.391(3) . ?
C1 C6 1.469(3) . ?
N2 N2 1.251(4) 2_756 ?
N2 C10 1.414(3) . ?
C8 C9 1.378(3) . ?
C8 C7 1.384(3) . ?
C11 C12 1.376(3) . ?
C11 C10 1.399(3) . ?
C7 C12 1.385(3) . ?
C3 C2 1.388(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.385(3) . ?
C4 H4 0.9500 . ?
C6 C6 1.331(4) 2_667 ?
C6 H6 0.9500 . ?
C2 H2 0.9500 . ?
C9 C10 1.396(3) . ?
C5 H5 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C4 N1 C3 116.7(2) . . ?
C2 C1 C5 117.1(2) . . ?
C2 C1 C6 120.0(2) . . ?
C5 C1 C6 122.9(2) . . ?
N2 N2 C10 114.5(2) 2_756 . ?
F1 C8 C9 118.54(19) . . ?
F1 C8 C7 119.63(19) . . ?
C9 C8 C7 121.8(2) . . ?
F3 C11 C12 118.8(2) . . ?
F3 C11 C10 119.43(19) . . ?
C12 C11 C10 121.8(2) . . ?
C8 C7 C12 117.4(2) . . ?
C8 C7 Br1 122.23(17) . . ?
C12 C7 Br1 120.40(16) . . ?
N1 C3 C2 123.7(2) . . ?
N1 C3 H3 118.2 . . ?
C2 C3 H3 118.2 . . ?
N1 C4 C5 123.9(2) . . ?
N1 C4 H4 118.0 . . ?
C5 C4 H4 118.0 . . ?
C6 C6 C1 126.1(3) 2_667 . ?
C6 C6 H6 117.0 2_667 . ?
C1 C6 H6 117.0 . . ?
C3 C2 C1 119.3(2) . . ?
C3 C2 H2 120.3 . . ?
C1 C2 H2 120.3 . . ?
F2 C9 C8 117.4(2) . . ?
F2 C9 C10 121.31(19) . . ?
C8 C9 C10 121.3(2) . . ?
C4 C5 C1 119.3(2) . . ?
C4 C5 H5 120.4 . . ?
C1 C5 H5 120.4 . . ?
C11 C10 C9 116.5(2) . . ?
C11 C10 N2 114.8(2) . . ?
C9 C10 N2 128.7(2) . . ?
F4 C12 C11 118.7(2) . . ?
F4 C12 C7 120.01(19) . . ?
C11 C12 C7 121.3(2) . . ?

_diffrn_measured_fraction_theta_max 0.985
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.992
_refine_diff_density_max         0.373
_refine_diff_density_min         -0.465
_refine_diff_density_rms         0.069
_database_code_depnum_ccdc_archive 'CCDC 984296'
#######################################################################
#
#                 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_(trans-1)(trans-ape)

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H8 Br2 F8 N6'
_chemical_formula_weight         668.16

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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

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

_cell_length_a                   5.9081(6)
_cell_length_b                   8.3193(9)
_cell_length_c                   23.198(2)
_cell_angle_alpha                94.9560(10)
_cell_angle_beta                 93.4810(10)
_cell_angle_gamma                95.8480(10)
_cell_volume                     1127.2(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1785
_cell_measurement_theta_min      2.47
_cell_measurement_theta_max      25.07

_exptl_crystal_description       plate
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.969
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             648
_exptl_absorpt_coefficient_mu    3.688
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4336
_exptl_absorpt_correction_T_max  0.7208
_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  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7322
_diffrn_reflns_av_R_equivalents  0.0579
_diffrn_reflns_av_sigmaI/netI    0.0979
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         0.88
_diffrn_reflns_theta_max         26.02
_reflns_number_total             4360
_reflns_number_gt                2668
_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)+(0.0132P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   constr
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0060(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4360
_refine_ls_number_parameters     344
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0672
_refine_ls_R_factor_gt           0.0362
_refine_ls_wR_factor_ref         0.0676
_refine_ls_wR_factor_gt          0.0615
_refine_ls_goodness_of_fit_ref   0.780
_refine_ls_restrained_S_all      0.780
_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
Br1 Br 0.42754(7) 0.77673(5) 0.260746(15) 0.04957(15) Uani 1 1 d . . .
Br2 Br 0.51459(7) 0.23749(5) 0.228778(15) 0.05134(15) Uani 1 1 d . . .
C2 C 0.1056(6) 0.7899(5) 0.34762(14) 0.0379(10) Uani 1 1 d . . .
C5 C 0.3623(6) 1.0213(5) 0.42051(14) 0.0379(10) Uani 1 1 d . . .
C6 C 0.4388(6) 0.9692(5) 0.36830(15) 0.0391(10) Uani 1 1 d . . .
C1 C 0.3158(6) 0.8527(5) 0.33066(14) 0.0355(9) Uani 1 1 d . . .
C3 C 0.0262(6) 0.8400(5) 0.39952(15) 0.0372(10) Uani 1 1 d . . .
C4 C 0.1515(6) 0.9579(5) 0.43784(14) 0.0339(9) Uani 1 1 d . . .
F2 F -0.1763(3) 0.7698(3) 0.41243(8) 0.0532(6) Uani 1 1 d . . .
F4 F 0.6459(3) 1.0351(3) 0.35499(8) 0.0534(6) Uani 1 1 d . . .
F1 F -0.0226(4) 0.6722(3) 0.31318(8) 0.0578(6) Uani 1 1 d . . .
F3 F 0.4920(4) 1.1377(3) 0.45532(8) 0.0548(6) Uani 1 1 d . . .
C9 C 0.8551(7) 0.0764(5) 0.17175(14) 0.0396(10) Uani 1 1 d . . .
C7 C 0.5945(6) 0.1864(5) 0.10970(16) 0.0418(10) Uani 1 1 d . . .
C10 C 0.9679(6) 0.0243(5) 0.12492(15) 0.0396(10) Uani 1 1 d . . .
C11 C 0.8987(6) 0.0516(5) 0.06886(14) 0.0371(10) Uani 1 1 d . . .
C12 C 0.7072(6) 0.1332(5) 0.06199(15) 0.0395(10) Uani 1 1 d . . .
C8 C 0.6650(6) 0.1586(5) 0.16486(14) 0.0385(10) Uani 1 1 d . . .
F9 F 0.6260(4) 0.1667(3) 0.00981(8) 0.0571(7) Uani 1 1 d . . .
F8 F 0.4120(4) 0.2664(3) 0.09989(9) 0.0586(6) Uani 1 1 d . . .
F6 F 1.1509(4) -0.0561(3) 0.13442(8) 0.0554(6) Uani 1 1 d . . .
F7 F 0.9321(4) 0.0455(3) 0.22522(8) 0.0587(7) Uani 1 1 d . . .
N5 N 0.3040(6) 0.3511(4) 0.33176(13) 0.0520(9) Uani 1 1 d . . .
C16 C 0.3683(6) 0.5183(5) 0.42180(15) 0.0441(10) Uani 1 1 d . . .
H15 H 0.4644 0.5945 0.4460 0.053 Uiso 1 1 calc R . .
C13 C 0.0975(7) 0.2974(5) 0.34884(16) 0.0522(11) Uani 1 1 d . . .
H18 H 0.0038 0.2222 0.3237 0.063 Uiso 1 1 calc R . .
C17 C 0.4320(7) 0.4595(5) 0.36829(16) 0.0485(11) Uani 1 1 d . . .
H14 H 0.5744 0.4986 0.3572 0.058 Uiso 1 1 calc R . .
C15 C 0.1544(6) 0.4591(5) 0.43823(14) 0.0391(10) Uani 1 1 d . . .
C14 C 0.0173(6) 0.3472(5) 0.40122(15) 0.0441(10) Uani 1 1 d . . .
H17 H -0.1259 0.3062 0.4112 0.053 Uiso 1 1 calc R . .
N6 N 0.6471(6) 0.6662(5) 0.15830(14) 0.0574(10) Uani 1 1 d . . .
C20 C 0.8950(7) 0.5530(5) 0.06851(15) 0.0415(10) Uani 1 1 d . . .
C18 C 0.8347(8) 0.5952(6) 0.16846(16) 0.0583(13) Uani 1 1 d . . .
H21 H 0.8810 0.5836 0.2068 0.070 Uiso 1 1 calc R . .
C21 C 0.7005(7) 0.6271(5) 0.05666(16) 0.0475(11) Uani 1 1 d . . .
H24 H 0.6505 0.6410 0.0188 0.057 Uiso 1 1 calc R . .
C19 C 0.9672(7) 0.5369(5) 0.12487(15) 0.0522(12) Uani 1 1 d . . .
H20 H 1.0989 0.4890 0.1338 0.063 Uiso 1 1 calc R . .
C22 C 0.5830(7) 0.6798(5) 0.10324(17) 0.0555(12) Uani 1 1 d . . .
H23 H 0.4504 0.7279 0.0955 0.067 Uiso 1 1 calc R . .
N4 N 0.0950(5) 0.5262(4) 0.49392(12) 0.0464(9) Uani 1 1 d . . .
N3 N 1.0331(5) 0.4903(4) 0.02474(11) 0.0473(9) Uani 1 1 d . . .
N1 N 0.0939(5) 1.0263(4) 0.49266(12) 0.0468(9) Uani 1 1 d . . .
N2 N 1.0344(5) -0.0080(4) 0.02501(10) 0.0451(9) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C1 1.872(3) . ?
Br2 C8 1.879(3) . ?
C2 F1 1.345(4) . ?
C2 C3 1.366(5) . ?
C2 C1 1.390(5) . ?
C5 F3 1.347(4) . ?
C5 C6 1.369(5) . ?
C5 C4 1.398(4) . ?
C6 F4 1.353(4) . ?
C6 C1 1.365(5) . ?
C3 F2 1.340(4) . ?
C3 C4 1.386(5) . ?
C4 N1 1.423(4) . ?
C9 F7 1.350(3) . ?
C9 C10 1.370(5) . ?
C9 C8 1.381(5) . ?
C7 F8 1.341(4) . ?
C7 C8 1.368(4) . ?
C7 C12 1.389(5) . ?
C10 F6 1.345(4) . ?
C10 C11 1.384(4) . ?
C11 C12 1.385(5) . ?
C11 N2 1.420(4) . ?
C12 F9 1.337(4) . ?
N5 C17 1.324(5) . ?
N5 C13 1.351(4) . ?
C16 C17 1.382(5) . ?
C16 C15 1.397(4) . ?
C13 C14 1.377(5) . ?
C15 C14 1.372(5) . ?
C15 N4 1.440(4) . ?
N6 C18 1.326(5) . ?
N6 C22 1.328(4) . ?
C20 C19 1.372(4) . ?
C20 C21 1.383(5) . ?
C20 N3 1.437(4) . ?
C18 C19 1.400(5) . ?
C21 C22 1.383(5) . ?
N4 N4 1.220(5) 2_566 ?
N3 N3 1.219(5) 2_765 ?
N1 N1 1.229(5) 2_576 ?
N2 N2 1.229(5) 2_755 ?

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
F1 C2 C3 118.1(3) . . ?
F1 C2 C1 119.8(3) . . ?
C3 C2 C1 122.1(4) . . ?
F3 C5 C6 119.0(3) . . ?
F3 C5 C4 119.6(3) . . ?
C6 C5 C4 121.3(4) . . ?
F4 C6 C1 120.0(3) . . ?
F4 C6 C5 117.8(4) . . ?
C1 C6 C5 122.3(4) . . ?
C6 C1 C2 116.6(3) . . ?
C6 C1 Br1 121.8(3) . . ?
C2 C1 Br1 121.6(3) . . ?
F2 C3 C2 117.6(3) . . ?
F2 C3 C4 121.1(3) . . ?
C2 C3 C4 121.3(4) . . ?
C3 C4 C5 116.4(3) . . ?
C3 C4 N1 128.9(3) . . ?
C5 C4 N1 114.7(3) . . ?
F7 C9 C10 118.9(3) . . ?
F7 C9 C8 120.1(3) . . ?
C10 C9 C8 121.1(3) . . ?
F8 C7 C8 120.7(3) . . ?
F8 C7 C12 117.6(3) . . ?
C8 C7 C12 121.7(4) . . ?
F6 C10 C9 118.3(3) . . ?
F6 C10 C11 119.7(3) . . ?
C9 C10 C11 122.1(4) . . ?
C10 C11 C12 116.8(3) . . ?
C10 C11 N2 115.5(3) . . ?
C12 C11 N2 127.7(3) . . ?
F9 C12 C11 121.8(3) . . ?
F9 C12 C7 117.3(3) . . ?
C11 C12 C7 120.8(3) . . ?
C7 C8 C9 117.6(3) . . ?
C7 C8 Br2 120.8(3) . . ?
C9 C8 Br2 121.6(3) . . ?
C17 N5 C13 116.5(3) . . ?
C17 C16 C15 117.5(4) . . ?
N5 C13 C14 124.0(4) . . ?
N5 C17 C16 124.5(4) . . ?
C14 C15 C16 119.4(3) . . ?
C14 C15 N4 125.3(3) . . ?
C16 C15 N4 115.3(3) . . ?
C15 C14 C13 118.2(4) . . ?
C18 N6 C22 117.0(4) . . ?
C19 C20 C21 120.0(4) . . ?
C19 C20 N3 116.1(3) . . ?
C21 C20 N3 123.9(3) . . ?
N6 C18 C19 123.8(4) . . ?
C20 C21 C22 117.5(4) . . ?
C20 C19 C18 117.4(4) . . ?
N6 C22 C21 124.3(4) . . ?
N4 N4 C15 113.2(4) 2_566 . ?
N3 N3 C20 114.4(4) 2_765 . ?
N1 N1 C4 114.8(4) 2_576 . ?
N2 N2 C11 115.4(4) 2_755 . ?

_diffrn_measured_fraction_theta_max 0.984
_diffrn_reflns_theta_full        26.02
_diffrn_measured_fraction_theta_full 0.984
_refine_diff_density_max         0.410
_refine_diff_density_min         -0.466
_refine_diff_density_rms         0.067
_database_code_depnum_ccdc_archive 'CCDC 984297'
#######################################################################
#
#                 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_(trans-2)(trans-bpe)

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H10 F8 I2 N4'
_chemical_formula_weight         760.16

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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

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

_cell_length_a                   5.8317(6)
_cell_length_b                   8.5364(9)
_cell_length_c                   23.470(3)
_cell_angle_alpha                95.7530(10)
_cell_angle_beta                 96.7480(10)
_cell_angle_gamma                95.8280(10)
_cell_volume                     1146.8(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    4009
_cell_measurement_theta_min      2.41
_cell_measurement_theta_max      27.32

_exptl_crystal_description       plate
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.09
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.201
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             720
_exptl_absorpt_coefficient_mu    2.831
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4357
_exptl_absorpt_correction_T_max  0.7767
_exptl_absorpt_process_details   SADABS

_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  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13012
_diffrn_reflns_av_R_equivalents  0.0341
_diffrn_reflns_av_sigmaI/netI    0.0465
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         0.88
_diffrn_reflns_theta_max         28.34
_reflns_number_total             5145
_reflns_number_gt                4079
_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)+(0.0394P)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    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5145
_refine_ls_number_parameters     343
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0478
_refine_ls_R_factor_gt           0.0315
_refine_ls_wR_factor_ref         0.0763
_refine_ls_wR_factor_gt          0.0698
_refine_ls_goodness_of_fit_ref   0.989
_refine_ls_restrained_S_all      0.989
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I 0.45076(4) 0.26333(3) 0.260469(10) 0.01445(8) Uani 1 1 d . . .
I2 I 0.48489(4) 0.26146(3) 0.766295(10) 0.01502(8) Uani 1 1 d . . .
C1 C 0.3220(6) 0.3491(5) 0.33630(16) 0.0128(8) Uani 1 1 d . . .
C2 C 0.1158(7) 0.2825(5) 0.35186(16) 0.0137(8) Uani 1 1 d . . .
C4 C 0.1547(7) 0.4620(5) 0.44008(16) 0.0135(8) Uani 1 1 d . . .
C5 C 0.3633(7) 0.5262(5) 0.42474(16) 0.0137(8) Uani 1 1 d . . .
C3 C 0.0307(6) 0.3362(5) 0.40199(16) 0.0134(8) Uani 1 1 d . . .
C6 C 0.4448(6) 0.4710(5) 0.37439(16) 0.0133(8) Uani 1 1 d . . .
F4 F -0.0078(4) 0.1577(3) 0.31834(9) 0.0174(5) Uani 1 1 d . . .
F2 F 0.4915(4) 0.6468(3) 0.45948(9) 0.0183(5) Uani 1 1 d . . .
F3 F -0.1736(4) 0.2641(3) 0.41225(9) 0.0170(5) Uani 1 1 d . . .
F1 F 0.6524(4) 0.5413(3) 0.36342(9) 0.0173(5) Uani 1 1 d . . .
N4 N 0.6464(6) 0.1564(4) 0.16364(15) 0.0205(8) Uani 1 1 d . . .
C8 C 0.9621(7) 0.0258(5) 0.13066(17) 0.0172(9) Uani 1 1 d . . .
H8 H 1.0948 -0.0272 0.1400 0.021 Uiso 1 1 calc R . .
C7 C 0.8888(7) 0.0475(5) 0.07370(16) 0.0141(8) Uani 1 1 d . . .
C11 C 0.5786(7) 0.1763(5) 0.10876(17) 0.0178(9) Uani 1 1 d . . .
H11 H 0.4449 0.2293 0.1008 0.021 Uiso 1 1 calc R . .
C12 C 0.6903(7) 0.1249(5) 0.06283(17) 0.0181(9) Uani 1 1 d . . .
H12 H 0.6336 0.1418 0.0246 0.022 Uiso 1 1 calc R . .
C9 C 0.8381(7) 0.0829(5) 0.17343(17) 0.0192(9) Uani 1 1 d . . .
H9 H 0.8918 0.0693 0.2122 0.023 Uiso 1 1 calc R . .
N3 N 0.6711(6) 0.1551(4) 0.66801(14) 0.0173(8) Uani 1 1 d . . .
C18 C 0.6140(7) -0.0216(5) 0.57956(17) 0.0171(9) Uani 1 1 d . . .
H18 H 0.5179 -0.1037 0.5549 0.020 Uiso 1 1 calc R . .
C16 C 0.9596(7) 0.1602(5) 0.60276(16) 0.0147(8) Uani 1 1 d . . .
H16 H 1.1054 0.2057 0.5942 0.018 Uiso 1 1 calc R . .
C17 C 0.8276(7) 0.0393(5) 0.56466(16) 0.0133(8) Uani 1 1 d . . .
C15 C 0.8755(7) 0.2129(5) 0.65301(17) 0.0177(9) Uani 1 1 d . . .
H15 H 0.9678 0.2950 0.6785 0.021 Uiso 1 1 calc R . .
C13 C 0.5442(7) 0.0400(5) 0.63106(16) 0.0153(8) Uani 1 1 d . . .
H13 H 0.3982 -0.0020 0.6406 0.018 Uiso 1 1 calc R . .
C22 C 0.1019(7) 0.4585(5) 0.93257(17) 0.0156(9) Uani 1 1 d . . .
C19 C 0.3270(7) 0.3500(5) 0.83739(17) 0.0142(8) Uani 1 1 d . . .
C24 C 0.1401(7) 0.4371(5) 0.83023(15) 0.0129(8) Uani 1 1 d . . .
C23 C 0.0304(6) 0.4893(5) 0.87643(16) 0.0144(8) Uani 1 1 d . . .
C21 C 0.2949(7) 0.3729(5) 0.93992(16) 0.0143(8) Uani 1 1 d . . .
C20 C 0.4011(7) 0.3215(5) 0.89338(17) 0.0157(8) Uani 1 1 d . . .
F6 F -0.1512(4) 0.5721(3) 0.86675(10) 0.0210(5) Uani 1 1 d . . .
F7 F 0.3828(4) 0.3391(3) 0.99208(9) 0.0205(5) Uani 1 1 d . . .
F5 F 0.0593(4) 0.4715(3) 0.77733(9) 0.0188(5) Uani 1 1 d . . .
F8 F 0.5859(4) 0.2386(3) 0.90340(10) 0.0215(5) Uani 1 1 d . . .
N1 N 0.0939(5) 0.5316(4) 0.49289(14) 0.0168(7) Uani 1 1 d . . .
N2 N -0.0257(6) 0.5199(4) 0.97553(14) 0.0192(8) Uani 1 1 d . . .
C25 C 1.0204(7) -0.0116(5) 0.02764(16) 0.0168(9) Uani 1 1 d . . .
H25 H 1.1445 -0.0710 0.0384 0.020 Uiso 1 1 calc R . .
C26 C 0.9047(6) -0.0261(5) 0.51045(16) 0.0146(8) Uani 1 1 d . . .
H26 H 0.8088 -0.1134 0.4886 0.018 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I1 C1 2.105(4) . ?
I2 C19 2.110(4) . ?
C1 C6 1.381(5) . ?
C1 C2 1.382(5) . ?
C2 F4 1.347(4) . ?
C2 C3 1.384(5) . ?
C4 C5 1.384(5) . ?
C4 C3 1.405(5) . ?
C4 N1 1.419(5) . ?
C5 F2 1.348(4) . ?
C5 C6 1.382(5) . ?
C3 F3 1.343(4) . ?
C6 F1 1.359(4) . ?
N4 C11 1.335(5) . ?
N4 C9 1.344(5) . ?
C8 C9 1.383(5) . ?
C8 C7 1.391(5) . ?
C7 C12 1.400(5) . ?
C7 C25 1.475(5) . ?
C11 C12 1.381(5) . ?
N3 C13 1.340(5) . ?
N3 C15 1.343(5) . ?
C18 C13 1.391(5) . ?
C18 C17 1.397(5) . ?
C16 C15 1.381(5) . ?
C16 C17 1.396(5) . ?
C17 C26 1.475(5) . ?
C22 C23 1.393(5) . ?
C22 C21 1.406(5) . ?
C22 N2 1.412(5) . ?
C19 C24 1.385(5) . ?
C19 C20 1.387(5) . ?
C24 F5 1.346(4) . ?
C24 C23 1.381(5) . ?
C23 F6 1.342(4) . ?
C21 F7 1.341(4) . ?
C21 C20 1.374(5) . ?
C20 F8 1.359(4) . ?
N1 N1 1.266(6) 2_566 ?
N2 N2 1.242(6) 2_567 ?
C25 C25 1.329(8) 2_755 ?
C26 C26 1.321(8) 2_756 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 C1 C2 116.4(4) . . ?
C6 C1 I1 121.5(3) . . ?
C2 C1 I1 122.0(3) . . ?
F4 C2 C1 119.9(3) . . ?
F4 C2 C3 117.5(3) . . ?
C1 C2 C3 122.6(4) . . ?
C5 C4 C3 116.4(4) . . ?
C5 C4 N1 115.5(3) . . ?
C3 C4 N1 128.1(4) . . ?
F2 C5 C6 118.5(3) . . ?
F2 C5 C4 119.5(3) . . ?
C6 C5 C4 122.0(4) . . ?
F3 C3 C2 117.4(3) . . ?
F3 C3 C4 121.9(3) . . ?
C2 C3 C4 120.6(4) . . ?
F1 C6 C1 120.6(3) . . ?
F1 C6 C5 117.5(3) . . ?
C1 C6 C5 121.8(4) . . ?
C11 N4 C9 116.3(4) . . ?
C9 C8 C7 118.7(4) . . ?
C8 C7 C12 117.8(4) . . ?
C8 C7 C25 119.4(4) . . ?
C12 C7 C25 122.9(3) . . ?
N4 C11 C12 124.3(4) . . ?
C11 C12 C7 118.8(4) . . ?
N4 C9 C8 124.2(4) . . ?
C13 N3 C15 116.6(4) . . ?
C13 C18 C17 118.9(4) . . ?
C15 C16 C17 119.2(4) . . ?
C16 C17 C18 117.5(4) . . ?
C16 C17 C26 123.0(4) . . ?
C18 C17 C26 119.5(4) . . ?
N3 C15 C16 123.9(4) . . ?
N3 C13 C18 123.8(4) . . ?
C23 C22 C21 116.3(4) . . ?
C23 C22 N2 116.0(3) . . ?
C21 C22 N2 127.7(4) . . ?
C24 C19 C20 116.5(4) . . ?
C24 C19 I2 121.4(3) . . ?
C20 C19 I2 122.1(3) . . ?
F5 C24 C23 118.4(3) . . ?
F5 C24 C19 120.2(3) . . ?
C23 C24 C19 121.4(3) . . ?
F6 C23 C24 118.7(3) . . ?
F6 C23 C22 119.1(3) . . ?
C24 C23 C22 122.2(4) . . ?
F7 C21 C20 117.6(3) . . ?
F7 C21 C22 121.8(3) . . ?
C20 C21 C22 120.6(3) . . ?
F8 C20 C21 117.7(3) . . ?
F8 C20 C19 119.4(3) . . ?
C21 C20 C19 122.9(4) . . ?
N1 N1 C4 114.6(4) 2_566 . ?
N2 N2 C22 115.5(4) 2_567 . ?
C25 C25 C7 125.4(5) 2_755 . ?
C26 C26 C17 125.8(5) 2_756 . ?

_diffrn_measured_fraction_theta_max 0.898
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         1.465
_refine_diff_density_min         -0.961
_refine_diff_density_rms         0.142
_database_code_depnum_ccdc_archive 'CCDC 984298'
#######################################################################
#
#                 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_(trans-2)(trans-ape)

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            trans-diiodooctafluoroazobenzene:azopyridine
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 N2 I2 F8, C10 H8 N4'
_chemical_formula_sum            'C22 H8 F8 I2 N6'
_chemical_formula_weight         762.14

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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

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

_cell_length_a                   5.8475(18)
_cell_length_b                   8.445(3)
_cell_length_c                   23.132(7)
_cell_angle_alpha                94.990(3)
_cell_angle_beta                 95.779(3)
_cell_angle_gamma                96.339(3)
_cell_volume                     1124.0(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    4116
_cell_measurement_theta_min      2.44
_cell_measurement_theta_max      28.00

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.244
_exptl_crystal_size_mid          0.172
_exptl_crystal_size_min          0.097
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.252
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             720
_exptl_absorpt_coefficient_mu    2.891
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6215
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   SADABS

_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  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11989
_diffrn_reflns_av_R_equivalents  0.0312
_diffrn_reflns_av_sigmaI/netI    0.0408
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         0.89
_diffrn_reflns_theta_max         26.35
_reflns_number_total             4570
_reflns_number_gt                3677
_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)+(0.0244P)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    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4570
_refine_ls_number_parameters     343
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0371
_refine_ls_R_factor_gt           0.0261
_refine_ls_wR_factor_ref         0.0575
_refine_ls_wR_factor_gt          0.0534
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_restrained_S_all      1.002
_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
I1 I 0.95635(4) 0.25805(3) 0.758405(9) 0.01357(7) Uani 1 1 d . . .
I2 I 0.00986(4) 0.74147(3) 0.736071(10) 0.01447(7) Uani 1 1 d . . .
F4 F 0.1236(3) 0.6655(3) 0.50797(8) 0.0207(5) Uani 1 1 d . . .
F8 F 1.1586(3) 0.5359(2) 0.86108(8) 0.0160(4) Uani 1 1 d . . .
F6 F 0.3313(3) 0.2573(2) 0.91389(8) 0.0166(5) Uani 1 1 d . . .
F2 F 0.4378(3) 0.5337(2) 0.72578(8) 0.0182(5) Uani 1 1 d . . .
F7 F 0.9962(3) 0.6450(2) 0.95795(8) 0.0170(5) Uani 1 1 d . . .
F1 F 0.6508(3) 0.4326(2) 0.63537(8) 0.0189(5) Uani 1 1 d . . .
F3 F -0.0843(3) 0.7644(2) 0.59738(9) 0.0205(5) Uani 1 1 d . . .
C1 C 0.4737(6) 0.1596(4) 0.09691(15) 0.0142(8) Uani 1 1 d . . .
H1 H 0.6203 0.2043 0.0877 0.017 Uiso 1 1 calc R . .
N1 N 0.4032(5) -0.0302(4) 0.00576(13) 0.0168(7) Uani 1 1 d . . .
N3 N 0.5367(5) -0.0124(4) 0.52529(12) 0.0184(7) Uani 1 1 d . . .
N4 N 0.1602(5) 0.1528(4) 0.65954(13) 0.0183(7) Uani 1 1 d . . .
C2 C 0.3883(6) 0.2122(4) 0.14795(15) 0.0159(8) Uani 1 1 d . . .
H2 H 0.4805 0.2938 0.1737 0.019 Uiso 1 1 calc R . .
C3 C 0.0538(6) 0.0392(4) 0.12652(15) 0.0151(8) Uani 1 1 d . . .
H3 H -0.0926 -0.0027 0.1367 0.018 Uiso 1 1 calc R . .
C11 C 0.4000(6) 0.5459(4) 0.56858(15) 0.0140(8) Uani 1 1 d . . .
C5 C 0.3385(6) 0.0391(4) 0.05946(14) 0.0129(8) Uani 1 1 d . . .
C15 C 0.0988(6) 0.6814(4) 0.60817(15) 0.0136(7) Uani 1 1 d . . .
C12 C 0.4696(6) 0.5157(4) 0.62536(15) 0.0145(8) Uani 1 1 d . . .
C10 C 0.2053(6) 0.1233(4) 0.55719(16) 0.0165(8) Uani 1 1 d . . .
H10 H 0.1506 0.1398 0.5183 0.020 Uiso 1 1 calc R . .
C20 C 0.6572(6) 0.4575(4) 0.94033(14) 0.0117(7) Uani 1 1 d . . .
C14 C 0.1699(6) 0.6537(4) 0.66446(15) 0.0144(8) Uani 1 1 d . . .
C7 C 0.4759(6) 0.0252(4) 0.62608(15) 0.0174(8) Uani 1 1 d . . .
H7 H 0.6094 -0.0267 0.6349 0.021 Uiso 1 1 calc R . .
C4 C 0.1240(6) -0.0221(4) 0.07435(15) 0.0144(8) Uani 1 1 d . . .
H4 H 0.0279 -0.1038 0.0495 0.017 Uiso 1 1 calc R . .
C16 C 0.2072(6) 0.6314(4) 0.56108(15) 0.0148(8) Uani 1 1 d . . .
C8 C 0.3519(6) 0.0797(4) 0.66994(16) 0.0171(8) Uani 1 1 d . . .
H8 H 0.4038 0.0651 0.7091 0.021 Uiso 1 1 calc R . .
C9 C 0.0924(6) 0.1737(4) 0.60405(16) 0.0188(8) Uani 1 1 d . . .
H9 H -0.0414 0.2262 0.5963 0.023 Uiso 1 1 calc R . .
F5 F 0.4948(3) 0.1528(2) 0.81778(8) 0.0169(5) Uani 1 1 d . . .
N2 N 0.1811(5) 0.1536(4) 0.16288(13) 0.0159(7) Uani 1 1 d . . .
N6 N 0.5974(5) 0.5273(4) 0.99365(13) 0.0163(7) Uani 1 1 d . . .
N5 N 0.5303(5) 0.4849(4) 0.52555(12) 0.0177(7) Uani 1 1 d . . .
C19 C 0.5348(5) 0.3314(4) 0.90197(14) 0.0113(7) Uani 1 1 d . . .
C22 C 0.9503(5) 0.4669(4) 0.87315(14) 0.0110(7) Uani 1 1 d . . .
C17 C 0.8279(6) 0.3443(4) 0.83521(14) 0.0113(7) Uani 1 1 d . . .
C13 C 0.3595(6) 0.5682(4) 0.67207(15) 0.0130(7) Uani 1 1 d . . .
C21 C 0.8687(6) 0.5229(4) 0.92395(15) 0.0120(7) Uani 1 1 d . . .
C18 C 0.6189(6) 0.2783(4) 0.85135(15) 0.0125(7) Uani 1 1 d . . .
C6 C 0.4015(6) 0.0478(4) 0.56920(15) 0.0138(8) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I1 C17 2.101(3) . ?
I2 C14 2.102(3) . ?
F4 C16 1.343(4) . ?
F8 C22 1.357(4) . ?
F6 C19 1.347(4) . ?
F2 C13 1.347(4) . ?
F7 C21 1.345(4) . ?
F1 C12 1.346(4) . ?
F3 C15 1.358(4) . ?
C1 C2 1.385(5) . ?
C1 C5 1.394(5) . ?
N1 N1 1.253(5) 2_655 ?
N1 C5 1.430(4) . ?
N3 N3 1.248(6) 2_656 ?
N3 C6 1.441(4) . ?
N4 C9 1.337(5) . ?
N4 C8 1.349(4) . ?
C2 N2 1.346(4) . ?
C3 N2 1.330(4) . ?
C3 C4 1.390(5) . ?
C11 C12 1.389(5) . ?
C11 C16 1.409(5) . ?
C11 N5 1.410(4) . ?
C5 C4 1.391(5) . ?
C15 C16 1.373(5) . ?
C15 C14 1.374(5) . ?
C12 C13 1.378(5) . ?
C10 C9 1.385(5) . ?
C10 C6 1.389(5) . ?
C20 C21 1.399(5) . ?
C20 C19 1.405(5) . ?
C20 N6 1.413(4) . ?
C14 C13 1.394(5) . ?
C7 C6 1.380(5) . ?
C7 C8 1.381(5) . ?
F5 C18 1.352(4) . ?
N6 N6 1.253(6) 2_667 ?
N5 N5 1.255(6) 2_666 ?
C19 C18 1.374(5) . ?
C22 C21 1.378(5) . ?
C22 C17 1.381(5) . ?
C17 C18 1.386(5) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C5 118.1(3) . . ?
N1 N1 C5 113.2(4) 2_655 . ?
N3 N3 C6 113.5(4) 2_656 . ?
C9 N4 C8 117.4(3) . . ?
N2 C2 C1 123.3(3) . . ?
N2 C3 C4 123.4(3) . . ?
C12 C11 C16 116.2(3) . . ?
C12 C11 N5 115.5(3) . . ?
C16 C11 N5 128.2(3) . . ?
C4 C5 C1 119.1(3) . . ?
C4 C5 N1 115.9(3) . . ?
C1 C5 N1 125.0(3) . . ?
F3 C15 C16 117.0(3) . . ?
F3 C15 C14 119.8(3) . . ?
C16 C15 C14 123.2(3) . . ?
F1 C12 C13 118.6(3) . . ?
F1 C12 C11 119.2(3) . . ?
C13 C12 C11 122.2(3) . . ?
C9 C10 C6 117.4(3) . . ?
C21 C20 C19 115.9(3) . . ?
C21 C20 N6 115.2(3) . . ?
C19 C20 N6 129.0(3) . . ?
C15 C14 C13 116.5(3) . . ?
C15 C14 I2 122.2(3) . . ?
C13 C14 I2 121.3(3) . . ?
C6 C7 C8 118.5(3) . . ?
C3 C4 C5 118.3(3) . . ?
F4 C16 C15 118.2(3) . . ?
F4 C16 C11 121.2(3) . . ?
C15 C16 C11 120.6(3) . . ?
N4 C8 C7 122.9(3) . . ?
N4 C9 C10 124.0(3) . . ?
C3 N2 C2 117.8(3) . . ?
N6 N6 C20 114.4(4) 2_667 . ?
N5 N5 C11 115.3(4) 2_666 . ?
F6 C19 C18 117.7(3) . . ?
F6 C19 C20 121.0(3) . . ?
C18 C19 C20 121.3(3) . . ?
F8 C22 C21 117.8(3) . . ?
F8 C22 C17 120.0(3) . . ?
C21 C22 C17 122.1(3) . . ?
C22 C17 C18 116.4(3) . . ?
C22 C17 I1 121.7(2) . . ?
C18 C17 I1 121.9(2) . . ?
F2 C13 C12 118.5(3) . . ?
F2 C13 C14 120.2(3) . . ?
C12 C13 C14 121.3(3) . . ?
F7 C21 C22 118.5(3) . . ?
F7 C21 C20 119.7(3) . . ?
C22 C21 C20 121.8(3) . . ?
F5 C18 C19 117.7(3) . . ?
F5 C18 C17 119.7(3) . . ?
C19 C18 C17 122.5(3) . . ?
C7 C6 C10 119.9(3) . . ?
C7 C6 N3 116.0(3) . . ?
C10 C6 N3 124.1(3) . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        26.35
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.725
_refine_diff_density_min         -0.672
_refine_diff_density_rms         0.118
_database_code_depnum_ccdc_archive 'CCDC 984299'
#######################################################################
#
#                 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_(trans-2)(cis-bpe)

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H10 F8 I2 N4'
_chemical_formula_weight         760.16

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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   C2/c

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

_cell_length_a                   11.0970(9)
_cell_length_b                   8.2444(7)
_cell_length_c                   26.821(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 91.4570(10)
_cell_angle_gamma                90.00
_cell_volume                     2453.1(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    3357
_cell_measurement_theta_min      3.04
_cell_measurement_theta_max      27.79

_exptl_crystal_description       block
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.07
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.058
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1440
_exptl_absorpt_coefficient_mu    2.647
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4942
_exptl_absorpt_correction_T_max  0.8447
_exptl_absorpt_process_details   SADABS

_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  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7658
_diffrn_reflns_av_R_equivalents  0.0253
_diffrn_reflns_av_sigmaI/netI    0.0313
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_theta_min         1.52
_diffrn_reflns_theta_max         28.32
_reflns_number_total             2804
_reflns_number_gt                2430
_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)+(0.0167P)²+1.0078P] 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         2804
_refine_ls_number_parameters     172
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0291
_refine_ls_R_factor_gt           0.0224
_refine_ls_wR_factor_ref         0.0446
_refine_ls_wR_factor_gt          0.0427
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_restrained_S_all      1.040
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I 0.276852(14) -0.14536(2) 0.616884(6) 0.01987(6) Uani 1 1 d . . .
F4 F 0.38053(13) 0.19017(17) 0.66293(5) 0.0239(3) Uani 1 1 d . . .
F3 F 0.46599(13) 0.45758(17) 0.62133(5) 0.0246(3) Uani 1 1 d . . .
F1 F 0.32569(16) -0.04502(19) 0.50298(5) 0.0399(4) Uani 1 1 d . . .
F2 F 0.41983(18) 0.2131(2) 0.46172(5) 0.0481(5) Uani 1 1 d . . .
N2 N 0.18663(19) 0.4120(3) 0.16184(7) 0.0216(5) Uani 1 1 d . . .
N1 N 0.5000(2) 0.4926(3) 0.52317(7) 0.0252(5) Uani 1 1 d . . .
C11 C 0.1505(2) 0.5403(3) 0.13526(9) 0.0216(6) Uani 1 1 d . . .
H11 H 0.1572 0.5355 0.1000 0.026 Uiso 1 1 calc R . .
C10 C 0.1040(2) 0.6799(3) 0.15579(9) 0.0197(6) Uani 1 1 d . . .
H10 H 0.0806 0.7685 0.1351 0.024 Uiso 1 1 calc R . .
C9 C 0.0917(2) 0.6889(3) 0.20753(9) 0.0166(5) Uani 1 1 d . . .
C12 C 0.0378(2) 0.8325(3) 0.23094(9) 0.0193(5) Uani 1 1 d . . .
H12 H 0.0589 0.9352 0.2177 0.023 Uiso 1 1 calc R . .
C7 C 0.1780(2) 0.4230(3) 0.21156(9) 0.0218(6) Uani 1 1 d . . .
H7 H 0.2044 0.3336 0.2313 0.026 Uiso 1 1 calc R . .
C8 C 0.1331(2) 0.5564(3) 0.23541(9) 0.0192(5) Uani 1 1 d . . .
H8 H 0.1302 0.5584 0.2708 0.023 Uiso 1 1 calc R . .
C1 C 0.3491(2) 0.0646(3) 0.58445(9) 0.0198(5) Uani 1 1 d . . .
C2 C 0.3612(3) 0.0783(3) 0.53320(9) 0.0264(6) Uani 1 1 d . . .
C3 C 0.4086(3) 0.2142(3) 0.51163(9) 0.0279(6) Uani 1 1 d . . .
C4 C 0.4467(2) 0.3472(3) 0.54012(9) 0.0214(5) Uani 1 1 d . . .
C6 C 0.3875(2) 0.1950(3) 0.61259(8) 0.0192(6) Uani 1 1 d . . .
C5 C 0.4337(2) 0.3332(3) 0.59167(9) 0.0193(5) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I1 C1 2.105(2) . ?
F4 C6 1.355(2) . ?
F3 C5 1.341(3) . ?
F1 C2 1.352(3) . ?
F2 C3 1.347(3) . ?
N2 C11 1.331(3) . ?
N2 C7 1.343(3) . ?
N1 N1 1.249(4) 5_666 ?
N1 C4 1.417(3) . ?
C11 C10 1.382(3) . ?
C11 H11 0.9500 . ?
C10 C9 1.400(3) . ?
C10 H10 0.9500 . ?
C9 C8 1.395(3) . ?
C9 C12 1.474(3) . ?
C12 C12 1.339(5) 2 ?
C12 H12 0.9500 . ?
C7 C8 1.372(3) . ?
C7 H7 0.9500 . ?
C8 H8 0.9500 . ?
C1 C6 1.375(3) . ?
C1 C2 1.389(3) . ?
C2 C3 1.372(4) . ?
C3 C4 1.396(3) . ?
C4 C5 1.399(3) . ?
C6 C5 1.375(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C11 N2 C7 116.7(2) . . ?
N1 N1 C4 114.4(3) 5_666 . ?
N2 C11 C10 124.0(2) . . ?
N2 C11 H11 118.0 . . ?
C10 C11 H11 118.0 . . ?
C11 C10 C9 119.1(2) . . ?
C11 C10 H10 120.5 . . ?
C9 C10 H10 120.5 . . ?
C8 C9 C10 116.8(2) . . ?
C8 C9 C12 122.2(2) . . ?
C10 C9 C12 121.0(2) . . ?
C12 C12 C9 126.45(13) 2 . ?
C12 C12 H12 116.8 2 . ?
C9 C12 H12 116.8 . . ?
N2 C7 C8 123.6(2) . . ?
N2 C7 H7 118.2 . . ?
C8 C7 H7 118.2 . . ?
C7 C8 C9 119.8(2) . . ?
C7 C8 H8 120.1 . . ?
C9 C8 H8 120.1 . . ?
C6 C1 C2 116.3(2) . . ?
C6 C1 I1 122.15(17) . . ?
C2 C1 I1 121.53(19) . . ?
F1 C2 C3 118.0(2) . . ?
F1 C2 C1 119.9(2) . . ?
C3 C2 C1 122.1(2) . . ?
F2 C3 C2 117.4(2) . . ?
F2 C3 C4 121.0(2) . . ?
C2 C3 C4 121.6(2) . . ?
C3 C4 C5 116.0(2) . . ?
C3 C4 N1 127.7(2) . . ?
C5 C4 N1 116.2(2) . . ?
F4 C6 C5 117.5(2) . . ?
F4 C6 C1 120.0(2) . . ?
C5 C6 C1 122.5(2) . . ?
F3 C5 C6 119.2(2) . . ?
F3 C5 C4 119.4(2) . . ?
C6 C5 C4 121.4(2) . . ?

_diffrn_measured_fraction_theta_max 0.919
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.402
_refine_diff_density_min         -0.400
_refine_diff_density_rms         0.089
_database_code_depnum_ccdc_archive 'CCDC 984300'
