# Electronic Supplementary Material (ESI) for CrystEngComm.
# 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_A1D8

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
TW-1-107 [2-(4-pyridyl)-imidazole]2, 1,4-diiodotetrafluorobenzene
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         
;
(C8 H7 N3)2 (C6 F4 I2)
;
_chemical_formula_sum            'C22 H14 F4 I2 N6'
_chemical_formula_weight         692.19

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   P2(1)/n

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

_cell_length_a                   12.9720(11)
_cell_length_b                   5.0426(4)
_cell_length_c                   17.0878(15)
_cell_angle_alpha                90.00
_cell_angle_beta                 92.470(4)
_cell_angle_gamma                90.00
_cell_volume                     1116.72(16)
_cell_formula_units_Z            2
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    9992
_cell_measurement_theta_min      3.14
_cell_measurement_theta_max      32.70

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.06
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.059
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             660
_exptl_absorpt_coefficient_mu    2.874
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.3782
_exptl_absorpt_correction_T_max  0.8465
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      120(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            17748
_diffrn_reflns_av_R_equivalents  0.0271
_diffrn_reflns_av_sigmaI/netI    0.0259
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         1.93
_diffrn_reflns_theta_max         32.56
_reflns_number_total             3962
_reflns_number_gt                3386
_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)+(0.0300P)²+0.8000P] 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         3962
_refine_ls_number_parameters     155
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0329
_refine_ls_R_factor_gt           0.0256
_refine_ls_wR_factor_ref         0.0622
_refine_ls_wR_factor_gt          0.0589
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_restrained_S_all      1.058
_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
N11A N 0.36473(14) 0.8137(3) 0.59714(10) 0.0183(3) Uani 0.20(4) 1 d P A 1
H11 H 0.3747 0.9746 0.5791 0.022 Uiso 0.20(4) 1 calc PR A 1
N11B N 0.36473(14) 0.8137(3) 0.59714(10) 0.0183(3) Uani 0.80(4) 1 d P A 2
C12 C 0.35176(15) 0.5917(4) 0.55588(11) 0.0156(3) Uani 1 1 d . . .
N13A N 0.33756(14) 0.3804(3) 0.60345(10) 0.0180(3) Uani 0.20(4) 1 d P A 1
N13B N 0.33756(14) 0.3804(3) 0.60345(10) 0.0180(3) Uani 0.80(4) 1 d P A 2
H13 H 0.3268 0.2153 0.5885 0.022 Uiso 0.80(4) 1 calc PR A 2
C14 C 0.34314(17) 0.4721(4) 0.67897(12) 0.0210(4) Uani 1 1 d . . .
H14 H 0.3371 0.3705 0.7254 0.025 Uiso 1 1 calc R A 1
C15 C 0.35915(16) 0.7378(4) 0.67402(12) 0.0201(4) Uani 1 1 d . A .
H15 H 0.3656 0.8546 0.7176 0.024 Uiso 1 1 calc R B 1
N21 N 0.35680(14) 0.5442(4) 0.30754(10) 0.0207(3) Uani 1 1 d . . .
C22 C 0.30450(17) 0.3680(4) 0.34869(12) 0.0205(4) Uani 1 1 d . A .
H22 H 0.2684 0.2309 0.3209 0.025 Uiso 1 1 calc R . .
C23 C 0.29987(16) 0.3735(4) 0.42938(12) 0.0186(4) Uani 1 1 d . . .
H23 H 0.2619 0.2431 0.4561 0.022 Uiso 1 1 calc R A .
C24 C 0.35218(15) 0.5747(4) 0.47089(11) 0.0158(3) Uani 1 1 d . A .
C25 C 0.40579(16) 0.7602(4) 0.42803(12) 0.0185(4) Uani 1 1 d . . .
H25 H 0.4418 0.9013 0.4539 0.022 Uiso 1 1 calc R A .
C26 C 0.40610(17) 0.7372(4) 0.34754(12) 0.0205(4) Uani 1 1 d . A .
H26 H 0.4432 0.8650 0.3192 0.025 Uiso 1 1 calc R . .
C31 C 0.47059(15) 0.1446(4) 0.06597(12) 0.0176(4) Uani 1 1 d . . .
I1 I 0.421719(10) 0.34197(3) 0.165311(7) 0.01899(5) Uani 1 1 d . . .
C32 C 0.54516(15) -0.0516(4) 0.07214(11) 0.0181(4) Uani 1 1 d . . .
F32 F 0.59176(10) -0.1067(3) 0.14199(7) 0.0239(3) Uani 1 1 d . . .
C36 C 0.42647(15) 0.1935(4) -0.00762(12) 0.0180(4) Uani 1 1 d . . .
F36 F 0.35527(10) 0.3855(3) -0.01777(8) 0.0243(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
N11A C12 1.330(3) . ?
N11A C15 1.373(3) . ?
N11A H11 0.8800 . ?
C12 N13A 1.358(3) . ?
C12 C24 1.455(3) . ?
N13A C14 1.370(3) . ?
C14 C15 1.359(3) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
N21 C22 1.336(3) . ?
N21 C26 1.336(3) . ?
N21 I1 2.7985(17) . ?
C22 C23 1.383(3) . ?
C22 H22 0.9500 . ?
C23 C24 1.397(3) . ?
C23 H23 0.9500 . ?
C24 C25 1.393(3) . ?
C25 C26 1.380(3) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?
C31 C36 1.381(3) . ?
C31 C32 1.384(3) . ?
C31 I1 2.090(2) . ?
C32 F32 1.343(2) . ?
C32 C36 1.378(3) 3_655 ?
C36 F36 1.344(2) . ?
C36 C32 1.378(3) 3_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
C12 N11A C15 105.20(17) . . ?
C12 N11A H11 127.4 . . ?
C15 N11A H11 127.4 . . ?
N11A C12 N13A 111.14(17) . . ?
N11A C12 C24 124.97(18) . . ?
N13A C12 C24 123.89(18) . . ?
C12 N13A C14 107.22(17) . . ?
C15 C14 N13A 106.03(18) . . ?
C15 C14 H14 127.0 . . ?
N13A C14 H14 127.0 . . ?
C14 C15 N11A 110.40(18) . . ?
C14 C15 H15 124.8 . . ?
N11A C15 H15 124.8 . . ?
C22 N21 C26 117.25(18) . . ?
C22 N21 I1 113.16(13) . . ?
C26 N21 I1 123.66(14) . . ?
N21 C22 C23 123.78(19) . . ?
N21 C22 H22 118.1 . . ?
C23 C22 H22 118.1 . . ?
C22 C23 C24 118.68(19) . . ?
C22 C23 H23 120.7 . . ?
C24 C23 H23 120.7 . . ?
C25 C24 C23 117.62(18) . . ?
C25 C24 C12 120.57(18) . . ?
C23 C24 C12 121.81(18) . . ?
C26 C25 C24 119.38(19) . . ?
C26 C25 H25 120.3 . . ?
C24 C25 H25 120.3 . . ?
N21 C26 C25 123.3(2) . . ?
N21 C26 H26 118.4 . . ?
C25 C26 H26 118.4 . . ?
C36 C31 C32 117.24(18) . . ?
C36 C31 I1 121.74(15) . . ?
C32 C31 I1 120.93(14) . . ?
C31 I1 N21 172.82(7) . . ?
F32 C32 C36 118.57(18) . 3_655 ?
F32 C32 C31 120.10(18) . . ?
C36 C32 C31 121.33(18) 3_655 . ?
F36 C36 C32 118.46(18) . 3_655 ?
F36 C36 C31 120.11(18) . . ?
C32 C36 C31 121.42(19) 3_655 . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C15 N11A C12 N13A 0.4(2) . . . . ?
C15 N11A C12 C24 -179.77(19) . . . . ?
N11A C12 N13A C14 -0.8(2) . . . . ?
C24 C12 N13A C14 179.38(19) . . . . ?
C12 N13A C14 C15 0.9(2) . . . . ?
N13A C14 C15 N11A -0.6(2) . . . . ?
C12 N11A C15 C14 0.1(2) . . . . ?
C26 N21 C22 C23 -0.7(3) . . . . ?
I1 N21 C22 C23 153.20(17) . . . . ?
N21 C22 C23 C24 0.3(3) . . . . ?
C22 C23 C24 C25 0.4(3) . . . . ?
C22 C23 C24 C12 -179.33(19) . . . . ?
N11A C12 C24 C25 26.2(3) . . . . ?
N13A C12 C24 C25 -154.0(2) . . . . ?
N11A C12 C24 C23 -154.0(2) . . . . ?
N13A C12 C24 C23 25.7(3) . . . . ?
C23 C24 C25 C26 -0.6(3) . . . . ?
C12 C24 C25 C26 179.10(19) . . . . ?
C22 N21 C26 C25 0.5(3) . . . . ?
I1 N21 C26 C25 -150.50(16) . . . . ?
C24 C25 C26 N21 0.2(3) . . . . ?
C36 C31 C32 F32 179.30(18) . . . . ?
I1 C31 C32 F32 -4.0(3) . . . . ?
C36 C31 C32 C36 -0.5(3) . . . 3_655 ?
I1 C31 C32 C36 176.16(15) . . . 3_655 ?
C32 C31 C36 F36 -178.52(18) . . . . ?
I1 C31 C36 F36 4.8(3) . . . . ?
C32 C31 C36 C32 0.5(3) . . . 3_655 ?
I1 C31 C36 C32 -176.13(15) . . . 3_655 ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N11A H11 N13A 0.88 2.15 2.882(2) 140.6 1_565
N13B H13 N11B 0.88 2.09 2.882(2) 149.7 1_545

_diffrn_measured_fraction_theta_max 0.975
_diffrn_reflns_theta_full        30.00
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         1.046
_refine_diff_density_min         -0.910
_refine_diff_density_rms         0.119
_database_code_depnum_ccdc_archive 'CCDC 994313'
#######################################################################
#
#                 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_A2D1

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C8 H7 N3), C2 F4 I2'
_chemical_formula_sum            'C18 H14 F4 I2 N6'
_chemical_formula_weight         644.15

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'
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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c
_symmetry_space_group_name_Hall  '-P 2ybc'

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

_cell_length_a                   12.3214(7)
_cell_length_b                   8.9036(5)
_cell_length_c                   9.8742(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 100.4930(10)
_cell_angle_gamma                90.00
_cell_volume                     1065.13(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9902
_cell_measurement_theta_min      2.84
_cell_measurement_theta_max      27.49

_exptl_crystal_description       rod
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.14
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_diffrn    2.008
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             612
_exptl_absorpt_coefficient_mu    3.004
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.3515
_exptl_absorpt_correction_T_max  0.6784
_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 CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_reflns_number            15508
_diffrn_reflns_av_R_equivalents  0.0315
_diffrn_reflns_av_sigmaI/netI    0.0172
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         1.68
_diffrn_reflns_theta_max         27.49
_reflns_number_total             2435
_reflns_number_gt                2327
_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)+(0.0328P)²+1.1200P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       'not measured'
_refine_ls_number_reflns         2435
_refine_ls_number_parameters     144
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0224
_refine_ls_R_factor_gt           0.0215
_refine_ls_wR_factor_ref         0.0570
_refine_ls_wR_factor_gt          0.0564
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_restrained_S_all      1.037
_refine_ls_shift/su_max          0.004
_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 -0.39973(6) -0.06697(8) -0.19783(6) 0.02377(12) Uani 0.953(4) 1 d P A 1
I1B I -0.4231(9) -0.0346(12) -0.2225(10) 0.02377(12) Uani 0.047(4) 1 d P A 2
F1 F -0.39086(16) -0.0977(2) 0.09716(17) 0.0519(5) Uani 1 1 d . A 1
F2 F -0.54533(19) -0.1836(2) -0.0240(2) 0.0640(6) Uani 1 1 d . A 1
N1 N -0.28619(17) -0.0662(2) -0.4249(2) 0.0267(4) Uani 1 1 d . . .
N2 N 0.01976(15) -0.3020(2) -0.35640(18) 0.0212(4) Uani 1 1 d . . .
N3 N 0.03668(15) -0.2786(2) -0.57511(18) 0.0201(4) Uani 1 1 d . . .
H3 H 0.023(3) -0.258(3) -0.659(3) 0.033(8) Uiso 1 1 d . . .
C1 C -0.4713(2) -0.0721(3) -0.0140(3) 0.0294(5) Uani 1 1 d . . .
C2 C -0.30891(19) 0.0241(3) -0.5348(2) 0.0282(5) Uani 1 1 d . A .
H2 H -0.3739 0.0837 -0.5462 0.034 Uiso 1 1 calc R . .
C3 C -0.2418(2) 0.0344(3) -0.6325(2) 0.0265(5) Uani 1 1 d . . .
H3A H -0.2609 0.0994 -0.7095 0.032 Uiso 1 1 calc R A .
C4 C -0.1463(2) -0.0513(2) -0.6170(2) 0.0223(4) Uani 1 1 d . A .
H4 H -0.0986 -0.0454 -0.6824 0.027 Uiso 1 1 calc R . .
C5 C -0.12171(17) -0.1465(2) -0.5031(2) 0.0186(4) Uani 1 1 d . . .
C6 C -0.19492(18) -0.1500(3) -0.4109(2) 0.0229(4) Uani 1 1 d . A .
H6 H -0.1790 -0.2155 -0.3340 0.028 Uiso 1 1 calc R . .
C7 C -0.02293(17) -0.2407(2) -0.4776(2) 0.0183(4) Uani 1 1 d . A .
C8 C 0.11022(19) -0.3819(3) -0.3791(2) 0.0241(4) Uani 1 1 d . . .
H8 H 0.1579 -0.4380 -0.3111 0.029 Uiso 1 1 calc R . .
C9 C 0.12157(18) -0.3688(3) -0.5134(2) 0.0238(4) Uani 1 1 d . . .
H9 H 0.1771 -0.4132 -0.5557 0.029 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 2.159(3) . ?
I1 N1 2.851(2) . ?
I1B C1 2.270(7) . ?
F1 C1 1.357(3) . ?
F2 C1 1.340(3) . ?
N1 C6 1.335(3) . ?
N1 C2 1.339(3) . ?
N2 C7 1.333(3) . ?
N2 C8 1.375(3) . ?
N3 C7 1.356(3) . ?
N3 C9 1.371(3) . ?
N3 H3 0.84(3) . ?
C1 C1 1.515(5) 3_455 ?
C2 C3 1.384(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.387(3) . ?
C3 H3A 0.9500 . ?
C4 C5 1.397(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.393(3) . ?
C5 C7 1.462(3) . ?
C6 H6 0.9500 . ?
C8 C9 1.364(3) . ?
C8 H8 0.9500 . ?
C9 H9 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
C1 I1 N1 174.73(10) . . ?
C6 N1 C2 117.8(2) . . ?
C6 N1 I1 116.26(15) . . ?
C2 N1 I1 125.37(15) . . ?
C7 N2 C8 105.34(17) . . ?
C7 N3 C9 107.34(17) . . ?
C7 N3 H3 128(2) . . ?
C9 N3 H3 125(2) . . ?
F2 C1 F1 108.8(2) . . ?
F2 C1 C1 107.9(3) . 3_455 ?
F1 C1 C1 107.0(3) . 3_455 ?
F2 C1 I1 109.30(17) . . ?
F1 C1 I1 109.46(17) . . ?
C1 C1 I1 114.2(2) 3_455 . ?
F2 C1 I1B 109.2(2) . . ?
F1 C1 I1B 119.0(4) . . ?
C1 C1 I1B 104.4(4) 3_455 . ?
I1 C1 I1B 11.2(4) . . ?
N1 C2 C3 122.8(2) . . ?
N1 C2 H2 118.6 . . ?
C3 C2 H2 118.6 . . ?
C2 C3 C4 119.3(2) . . ?
C2 C3 H3A 120.3 . . ?
C4 C3 H3A 120.3 . . ?
C3 C4 C5 118.5(2) . . ?
C3 C4 H4 120.7 . . ?
C5 C4 H4 120.7 . . ?
C6 C5 C4 117.9(2) . . ?
C6 C5 C7 119.46(19) . . ?
C4 C5 C7 122.59(19) . . ?
N1 C6 C5 123.6(2) . . ?
N1 C6 H6 118.2 . . ?
C5 C6 H6 118.2 . . ?
N2 C7 N3 111.09(19) . . ?
N2 C7 C5 124.74(18) . . ?
N3 C7 C5 124.16(18) . . ?
C9 C8 N2 110.14(19) . . ?
C9 C8 H8 124.9 . . ?
N2 C8 H8 124.9 . . ?
C8 C9 N3 106.10(19) . . ?
C8 C9 H9 127.0 . . ?
N3 C9 H9 127.0 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N3 H3 N2 0.84(3) 2.01(3) 2.839(2) 169(3) 4

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.913
_refine_diff_density_min         -0.609
_refine_diff_density_rms         0.087
_database_code_depnum_ccdc_archive 'CCDC 994314'
#######################################################################
#
#                 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_A2D2

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
TW-2-07 [2-(3-pyridyl)-imidazole]2, I-(CF2)4-I
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         
;
(C8 H7 N3)2 (C4 F8 I2)
;
_chemical_formula_sum            'C20 H14 F8 I2 N6'
_chemical_formula_weight         744.17

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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   P2(1)/c

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

_cell_length_a                   14.3500(9)
_cell_length_b                   8.7642(5)
_cell_length_c                   9.9637(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 106.551(2)
_cell_angle_gamma                90.00
_cell_volume                     1201.18(12)
_cell_formula_units_Z            2
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    9903
_cell_measurement_theta_min      2.92
_cell_measurement_theta_max      33.81

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.16
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.058
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             708
_exptl_absorpt_coefficient_mu    2.702
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4978
_exptl_absorpt_correction_T_max  0.6717
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      120(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            21724
_diffrn_reflns_av_R_equivalents  0.0245
_diffrn_reflns_av_sigmaI/netI    0.0198
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.48
_diffrn_reflns_theta_max         33.14
_reflns_number_total             4223
_reflns_number_gt                3853
_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)+(0.0250P)²+1.5000P] 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         4223
_refine_ls_number_parameters     164
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0321
_refine_ls_R_factor_gt           0.0284
_refine_ls_wR_factor_ref         0.0639
_refine_ls_wR_factor_gt          0.0626
_refine_ls_goodness_of_fit_ref   1.110
_refine_ls_restrained_S_all      1.110
_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
N11 N 0.25062(14) 0.5281(2) 0.53667(19) 0.0245(4) Uani 1 1 d . . .
C12 C 0.32738(15) 0.6210(2) 0.56137(19) 0.0200(4) Uani 1 1 d . . .
H12 H 0.3417 0.6830 0.6429 0.024 Uiso 1 1 calc R . .
C13 C 0.38775(14) 0.6319(2) 0.47405(18) 0.0162(3) Uani 1 1 d . . .
C14 C 0.36405(16) 0.5432(2) 0.3528(2) 0.0202(4) Uani 1 1 d . . .
H14 H 0.4027 0.5474 0.2897 0.024 Uiso 1 1 calc R . .
C15 C 0.28382(17) 0.4492(3) 0.3259(2) 0.0251(4) Uani 1 1 d . . .
H15 H 0.2659 0.3890 0.2432 0.030 Uiso 1 1 calc R . .
C16 C 0.22945(17) 0.4435(3) 0.4209(2) 0.0253(4) Uani 1 1 d . . .
H16 H 0.1751 0.3767 0.4026 0.030 Uiso 1 1 calc R . .
N21 N 0.52399(12) 0.7745(2) 0.42463(16) 0.0174(3) Uani 1 1 d . . .
H21 H 0.5125 0.7471 0.3364 0.021 Uiso 0.81(4) 1 calc PR . .
C22 C 0.47211(14) 0.7321(2) 0.51282(18) 0.0159(3) Uani 1 1 d . . .
N23 N 0.50926(13) 0.7933(2) 0.63926(16) 0.0185(3) Uani 1 1 d . . .
H23 H 0.4880 0.7819 0.7133 0.022 Uiso 0.19(4) 1 calc PR . .
C24 C 0.58755(16) 0.8776(3) 0.6297(2) 0.0215(4) Uani 1 1 d . . .
H24 H 0.6289 0.9348 0.7041 0.026 Uiso 1 1 calc R . .
C25 C 0.59745(15) 0.8676(2) 0.4976(2) 0.0203(4) Uani 1 1 d . . .
H25 H 0.6455 0.9156 0.4634 0.024 Uiso 1 1 calc R . .
I1 I 0.151865(10) 0.554190(17) 0.744972(13) 0.02315(5) Uani 1 1 d . . .
C31 C 0.09691(17) 0.6034(3) 0.9200(2) 0.0240(4) Uani 1 1 d . . .
F31A F 0.05614(13) 0.74157(18) 0.90483(18) 0.0418(4) Uani 1 1 d . . .
F31B F 0.17208(12) 0.6072(2) 1.03805(15) 0.0412(4) Uani 1 1 d . . .
C32 C 0.02295(15) 0.4842(2) 0.9398(2) 0.0190(4) Uani 1 1 d . . .
F32A F -0.04863(11) 0.4753(2) 0.82025(14) 0.0365(4) Uani 1 1 d . . .
F32B F 0.06900(12) 0.34962(17) 0.96376(17) 0.0354(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
N11 C16 1.332(3) . ?
N11 C12 1.335(3) . ?
N11 I1 2.8362(18) . ?
C12 C13 1.395(2) . ?
C12 H12 0.9500 . ?
C13 C14 1.395(3) . ?
C13 C22 1.455(3) . ?
C14 C15 1.378(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.388(3) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
N21 C22 1.356(2) . ?
N21 C25 1.367(3) . ?
N21 H21 0.8800 . ?
C22 N23 1.333(2) . ?
N23 C24 1.371(3) . ?
N23 H23 0.8800 . ?
C24 C25 1.366(3) . ?
C24 H24 0.9500 . ?
C25 H25 0.9500 . ?
I1 C31 2.152(2) . ?
C31 F31A 1.335(3) . ?
C31 F31B 1.351(3) . ?
C31 C32 1.541(3) . ?
C32 F32A 1.336(2) . ?
C32 F32B 1.340(2) . ?
C32 C32 1.548(4) 3_567 ?

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
C16 N11 C12 118.16(18) . . ?
C16 N11 I1 129.84(15) . . ?
C12 N11 I1 111.96(13) . . ?
N11 C12 C13 123.60(18) . . ?
N11 C12 H12 118.2 . . ?
C13 C12 H12 118.2 . . ?
C14 C13 C12 117.39(18) . . ?
C14 C13 C22 123.05(16) . . ?
C12 C13 C22 119.56(17) . . ?
C15 C14 C13 119.07(18) . . ?
C15 C14 H14 120.5 . . ?
C13 C14 H14 120.5 . . ?
C14 C15 C16 119.3(2) . . ?
C14 C15 H15 120.3 . . ?
C16 C15 H15 120.3 . . ?
N11 C16 C15 122.4(2) . . ?
N11 C16 H16 118.8 . . ?
C15 C16 H16 118.8 . . ?
C22 N21 C25 107.58(15) . . ?
C22 N21 H21 126.2 . . ?
C25 N21 H21 126.2 . . ?
N23 C22 N21 110.89(17) . . ?
N23 C22 C13 124.90(16) . . ?
N21 C22 C13 124.21(16) . . ?
C22 N23 C24 105.44(15) . . ?
C22 N23 H23 127.3 . . ?
C24 N23 H23 127.3 . . ?
C25 C24 N23 110.17(18) . . ?
C25 C24 H24 124.9 . . ?
N23 C24 H24 124.9 . . ?
C24 C25 N21 105.92(17) . . ?
C24 C25 H25 127.0 . . ?
N21 C25 H25 127.0 . . ?
C31 I1 N11 169.70(8) . . ?
F31A C31 F31B 107.0(2) . . ?
F31A C31 C32 109.50(18) . . ?
F31B C31 C32 108.25(17) . . ?
F31A C31 I1 109.87(13) . . ?
F31B C31 I1 108.93(14) . . ?
C32 C31 I1 113.13(14) . . ?
F32A C32 F32B 108.80(18) . . ?
F32A C32 C31 107.92(17) . . ?
F32B C32 C31 107.26(17) . . ?
F32A C32 C32 108.2(2) . 3_567 ?
F32B C32 C32 108.5(2) . 3_567 ?
C31 C32 C32 116.0(2) . 3_567 ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C16 N11 C12 C13 -1.4(3) . . . . ?
I1 N11 C12 C13 -179.17(15) . . . . ?
N11 C12 C13 C14 1.8(3) . . . . ?
N11 C12 C13 C22 -177.49(19) . . . . ?
C12 C13 C14 C15 -0.5(3) . . . . ?
C22 C13 C14 C15 178.69(19) . . . . ?
C13 C14 C15 C16 -0.9(3) . . . . ?
C12 N11 C16 C15 -0.3(3) . . . . ?
I1 N11 C16 C15 177.09(16) . . . . ?
C14 C15 C16 N11 1.4(4) . . . . ?
C25 N21 C22 N23 -0.3(2) . . . . ?
C25 N21 C22 C13 -179.76(18) . . . . ?
C14 C13 C22 N23 -165.02(19) . . . . ?
C12 C13 C22 N23 14.2(3) . . . . ?
C14 C13 C22 N21 14.4(3) . . . . ?
C12 C13 C22 N21 -166.39(19) . . . . ?
N21 C22 N23 C24 0.1(2) . . . . ?
C13 C22 N23 C24 179.56(19) . . . . ?
C22 N23 C24 C25 0.1(2) . . . . ?
N23 C24 C25 N21 -0.3(2) . . . . ?
C22 N21 C25 C24 0.4(2) . . . . ?
C16 N11 I1 C31 -178.6(4) . . . . ?
C12 N11 I1 C31 -1.2(5) . . . . ?
N11 I1 C31 F31A 72.8(5) . . . . ?
N11 I1 C31 F31B -44.1(5) . . . . ?
N11 I1 C31 C32 -164.5(3) . . . . ?
F31A C31 C32 F32A 66.9(2) . . . . ?
F31B C31 C32 F32A -176.81(18) . . . . ?
I1 C31 C32 F32A -56.0(2) . . . . ?
F31A C31 C32 F32B -176.01(17) . . . . ?
F31B C31 C32 F32B -59.7(2) . . . . ?
I1 C31 C32 F32B 61.08(19) . . . . ?
F31A C31 C32 C32 -54.6(3) . . . 3_567 ?
F31B C31 C32 C32 61.6(3) . . . 3_567 ?
I1 C31 C32 C32 -177.55(18) . . . 3_567 ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N21 H21 N23 0.88 1.98 2.853(2) 169.2 4_575
N23 H23 N21 0.88 2.08 2.853(2) 146.1 4_576

_diffrn_measured_fraction_theta_max 0.923
_diffrn_reflns_theta_full        27.50
_diffrn_measured_fraction_theta_full 0.986
_refine_diff_density_max         1.394
_refine_diff_density_min         -0.763
_refine_diff_density_rms         0.105
_database_code_depnum_ccdc_archive 'CCDC 994315'
#######################################################################
#
#                 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_A2D7

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 F4 I2, 2(C8 H7 N3) '
_chemical_formula_sum            'C22 H14 F4 I2 N6'
_chemical_formula_weight         692.19

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   Cm
_symmetry_space_group_name_Hall  'C -2y '

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

_cell_length_a                   10.0009(13)
_cell_length_b                   28.964(4)
_cell_length_c                   4.1036(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 100.997(2)
_cell_angle_gamma                90.00
_cell_volume                     1166.8(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    6018
_cell_measurement_theta_min      2.81
_cell_measurement_theta_max      26.40

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.970
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             660
_exptl_absorpt_coefficient_mu    2.750
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4925
_exptl_absorpt_correction_T_max  0.7705
_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            8684
_diffrn_reflns_av_R_equivalents  0.0344
_diffrn_reflns_av_sigmaI/netI    0.0335
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -36
_diffrn_reflns_limit_k_max       35
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_limit_l_max       5
_diffrn_reflns_theta_min         1.41
_diffrn_reflns_theta_max         26.48
_reflns_number_total             2217
_reflns_number_gt                2118
_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)+(0.0258P)²+0.0060P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.01(2)
_refine_ls_number_reflns         2217
_refine_ls_number_parameters     157
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0221
_refine_ls_R_factor_gt           0.0203
_refine_ls_wR_factor_ref         0.0470
_refine_ls_wR_factor_gt          0.0462
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_restrained_S_all      1.023
_refine_ls_shift/su_max          0.020
_refine_ls_shift/su_mean         0.002

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I 0.74317(4) 0.435255(6) 0.51296(5) 0.01813(7) Uani 1 1 d . . .
F1 F 1.2271(2) 0.45321(8) 0.1393(6) 0.0304(5) Uani 1 1 d . . .
F2 F 1.0175(3) 0.40621(8) 0.3031(7) 0.0301(6) Uani 1 1 d . . .
C2 C 1.0132(4) 0.45269(13) 0.3082(9) 0.0192(7) Uani 1 1 d . . .
C3 C 1.1213(4) 0.47626(13) 0.2238(9) 0.0201(7) Uani 1 1 d . . .
C1 C 0.9037(3) 0.47563(11) 0.3953(8) 0.0157(7) Uani 1 1 d . . .
N3 N 0.5275(3) 0.37671(11) 0.6338(8) 0.0226(7) Uani 1 1 d . . .
C11 C 0.2954(4) 0.32179(13) 0.5894(9) 0.0183(7) Uani 1 1 d . . .
H11A H 0.2159 0.3034 0.5753 0.022 Uiso 1 1 calc R . .
N2 N 0.5170(3) 0.24116(11) 0.2107(8) 0.0205(7) Uani 1 1 d . . .
N1 N 0.2953(3) 0.23453(11) 0.1993(8) 0.0184(6) Uani 1 1 d D . .
H1N H 0.214(3) 0.2442(13) 0.218(11) 0.022 Uiso 1 1 d D . .
C7 C 0.4072(3) 0.30554(12) 0.4599(8) 0.0160(7) Uani 1 1 d . . .
C5 C 0.4710(4) 0.20008(13) 0.0610(10) 0.0214(8) Uani 1 1 d . . .
H5A H 0.5263 0.1783 -0.0244 0.026 Uiso 1 1 calc R . .
C4 C 0.3355(4) 0.19520(13) 0.0529(10) 0.0222(8) Uani 1 1 d . . .
H4A H 0.2796 0.1699 -0.0354 0.027 Uiso 1 1 calc R . .
C6 C 0.4087(3) 0.26080(12) 0.2945(9) 0.0167(7) Uani 1 1 d . . .
C8 C 0.5194(4) 0.33527(12) 0.4892(10) 0.0203(8) Uani 1 1 d . . .
H8A H 0.5953 0.3252 0.3996 0.024 Uiso 1 1 calc R . .
C10 C 0.3028(4) 0.36485(13) 0.7375(9) 0.0195(8) Uani 1 1 d . . .
H10A H 0.2285 0.3763 0.8271 0.023 Uiso 1 1 calc R . .
C9 C 0.4196(4) 0.39099(14) 0.7538(10) 0.0222(9) Uani 1 1 d . . .
H9A H 0.4232 0.4206 0.8553 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 2.115(3) . ?
F1 C3 1.352(4) . ?
F2 C2 1.347(5) . ?
C2 C3 1.377(5) . ?
C2 C1 1.385(5) . ?
C3 C3 1.375(7) 2_565 ?
C1 C1 1.412(7) 2_565 ?
N3 C8 1.334(5) . ?
N3 C9 1.335(5) . ?
C11 C10 1.383(5) . ?
C11 C7 1.407(5) . ?
C11 H11A 0.9500 . ?
N2 C6 1.326(4) . ?
N2 C5 1.377(5) . ?
N1 C6 1.360(4) . ?
N1 C4 1.383(5) . ?
N1 H1N 0.879(18) . ?
C7 C8 1.401(5) . ?
C7 C6 1.464(5) . ?
C5 C4 1.357(5) . ?
C5 H5A 0.9500 . ?
C4 H4A 0.9500 . ?
C8 H8A 0.9500 . ?
C10 C9 1.382(6) . ?
C10 H10A 0.9500 . ?
C9 H9A 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
F2 C2 C3 117.6(3) . . ?
F2 C2 C1 120.8(3) . . ?
C3 C2 C1 121.6(3) . . ?
F1 C3 C3 119.60(18) . 2_565 ?
F1 C3 C2 120.7(3) . . ?
C3 C3 C2 119.7(2) 2_565 . ?
C2 C1 C1 118.7(2) . 2_565 ?
C2 C1 I1 117.8(2) . . ?
C1 C1 I1 123.57(9) 2_565 . ?
C8 N3 C9 117.3(3) . . ?
C10 C11 C7 119.2(3) . . ?
C10 C11 H11A 120.4 . . ?
C7 C11 H11A 120.4 . . ?
C6 N2 C5 105.4(3) . . ?
C6 N1 C4 106.9(3) . . ?
C6 N1 H1N 122(3) . . ?
C4 N1 H1N 131(3) . . ?
C11 C7 C8 116.3(3) . . ?
C11 C7 C6 123.4(3) . . ?
C8 C7 C6 120.3(3) . . ?
C4 C5 N2 110.4(3) . . ?
C4 C5 H5A 124.8 . . ?
N2 C5 H5A 124.8 . . ?
C5 C4 N1 106.0(3) . . ?
C5 C4 H4A 127.0 . . ?
N1 C4 H4A 127.0 . . ?
N2 C6 N1 111.3(3) . . ?
N2 C6 C7 125.5(3) . . ?
N1 C6 C7 123.2(3) . . ?
N3 C8 C7 124.8(3) . . ?
N3 C8 H8A 117.6 . . ?
C7 C8 H8A 117.6 . . ?
C9 C10 C11 119.3(3) . . ?
C9 C10 H10A 120.4 . . ?
C11 C10 H10A 120.4 . . ?
N3 C9 C10 123.2(4) . . ?
N3 C9 H9A 118.4 . . ?
C10 C9 H9A 118.4 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
F2 C2 C3 F1 0.0(5) . . . . ?
C1 C2 C3 F1 -179.9(3) . . . . ?
F2 C2 C3 C3 179.7(2) . . . 2_565 ?
C1 C2 C3 C3 -0.3(4) . . . 2_565 ?
F2 C2 C1 C1 -179.7(2) . . . 2_565 ?
C3 C2 C1 C1 0.3(4) . . . 2_565 ?
F2 C2 C1 I1 -0.8(5) . . . . ?
C3 C2 C1 I1 179.2(3) . . . . ?
C10 C11 C7 C8 -0.6(5) . . . . ?
C10 C11 C7 C6 -179.1(3) . . . . ?
C6 N2 C5 C4 0.4(4) . . . . ?
N2 C5 C4 N1 0.5(4) . . . . ?
C6 N1 C4 C5 -1.2(4) . . . . ?
C5 N2 C6 N1 -1.2(4) . . . . ?
C5 N2 C6 C7 -179.6(4) . . . . ?
C4 N1 C6 N2 1.5(4) . . . . ?
C4 N1 C6 C7 179.9(3) . . . . ?
C11 C7 C6 N2 -169.9(3) . . . . ?
C8 C7 C6 N2 11.7(5) . . . . ?
C11 C7 C6 N1 11.9(5) . . . . ?
C8 C7 C6 N1 -166.5(3) . . . . ?
C9 N3 C8 C7 -1.2(6) . . . . ?
C11 C7 C8 N3 1.2(5) . . . . ?
C6 C7 C8 N3 179.7(3) . . . . ?
C7 C11 C10 C9 0.3(5) . . . . ?
C8 N3 C9 C10 0.7(6) . . . . ?
C11 C10 C9 N3 -0.3(6) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1N N2 0.879(18) 2.01(2) 2.879(4) 171(4) 4_455
C11 H11A N2 0.95 2.59 3.441(5) 148.8 4_455

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.408
_refine_diff_density_min         -0.452
_refine_diff_density_rms         0.074
_database_code_depnum_ccdc_archive 'CCDC 994316'
#######################################################################
#
#                 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_A2D8

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
TW-2-27 [2-(3-pyridyl)-imidazole]2, 1,4-diiodotetrafluorobenzene
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         
;
(C8 H7 N3)2 (C6 F4 I2)
;
_chemical_formula_sum            'C22 H14 F4 I2 N6'
_chemical_formula_weight         692.19

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   P2(1)/c

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

_cell_length_a                   4.1462(3)
_cell_length_b                   27.9646(17)
_cell_length_c                   9.9124(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 100.094(2)
_cell_angle_gamma                90.00
_cell_volume                     1131.52(13)
_cell_formula_units_Z            2
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    8525
_cell_measurement_theta_min      2.55
_cell_measurement_theta_max      32.55

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.06
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.032
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             660
_exptl_absorpt_coefficient_mu    2.836
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5259
_exptl_absorpt_correction_T_max  0.8483
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      120(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            13291
_diffrn_reflns_av_R_equivalents  0.0211
_diffrn_reflns_av_sigmaI/netI    0.0263
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -42
_diffrn_reflns_limit_k_max       39
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         1.46
_diffrn_reflns_theta_max         32.58
_reflns_number_total             3850
_reflns_number_gt                3433
_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)+(0.0300P)²+0.7000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3850
_refine_ls_number_parameters     157
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0301
_refine_ls_R_factor_gt           0.0254
_refine_ls_wR_factor_ref         0.0607
_refine_ls_wR_factor_gt          0.0586
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_restrained_S_all      1.022
_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
N11 N 0.7683(4) 0.23506(6) 0.75966(16) 0.0168(3) Uani 1 1 d . . .
H11 H 0.741(6) 0.2437(9) 0.842(3) 0.020 Uiso 1 1 d . . .
C12 C 0.6742(5) 0.26223(7) 0.64663(18) 0.0155(3) Uani 1 1 d . . .
N13 N 0.7578(5) 0.24164(6) 0.53706(16) 0.0189(3) Uani 1 1 d . . .
C14 C 0.9100(6) 0.19972(7) 0.5834(2) 0.0213(4) Uani 1 1 d . . .
H14 H 0.9972 0.1771 0.5279 0.026 Uiso 1 1 calc R . .
C15 C 0.9178(5) 0.19520(7) 0.7204(2) 0.0201(4) Uani 1 1 d . . .
H15 H 1.0089 0.1695 0.7774 0.024 Uiso 1 1 calc R . .
N21 N 0.3358(5) 0.38059(7) 0.52470(18) 0.0227(4) Uani 1 1 d . . .
C22 C 0.4798(5) 0.33769(8) 0.5335(2) 0.0198(4) Uani 1 1 d . . .
H22 H 0.5694 0.3269 0.4571 0.024 Uiso 1 1 calc R . .
C23 C 0.5070(5) 0.30788(7) 0.64700(18) 0.0157(3) Uani 1 1 d . . .
C24 C 0.3745(5) 0.32447(7) 0.7583(2) 0.0178(4) Uani 1 1 d . . .
H24 H 0.3862 0.3055 0.8384 0.021 Uiso 1 1 calc R . .
C25 C 0.2262(5) 0.36883(8) 0.7505(2) 0.0212(4) Uani 1 1 d . . .
H25 H 0.1360 0.3808 0.8255 0.025 Uiso 1 1 calc R . .
C26 C 0.2105(5) 0.39554(8) 0.6323(2) 0.0219(4) Uani 1 1 d . . .
H26 H 0.1060 0.4259 0.6275 0.026 Uiso 1 1 calc R . .
C31 C 0.4644(5) 0.47357(7) 0.1183(2) 0.0169(4) Uani 1 1 d . . .
I1 I 0.40774(3) 0.435455(5) 0.294513(12) 0.01839(5) Uani 1 1 d . . .
C32 C 0.3544(5) 0.52009(7) 0.09883(19) 0.0167(4) Uani 1 1 d . . .
F32 F 0.2036(3) 0.54129(5) 0.19235(12) 0.0244(3) Uani 1 1 d . . .
C36 C 0.6108(5) 0.45407(7) 0.0167(2) 0.0173(4) Uani 1 1 d . . .
F36 F 0.7240(3) 0.40901(4) 0.02723(13) 0.0245(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
N11 C12 1.353(2) . ?
N11 C15 1.365(3) . ?
N11 H11 0.88(3) . ?
C12 N13 1.328(2) . ?
C12 C23 1.453(3) . ?
N13 C14 1.372(3) . ?
C14 C15 1.359(3) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
N21 C26 1.333(3) . ?
N21 C22 1.336(3) . ?
N21 I1 2.8085(18) . ?
C22 C23 1.389(3) . ?
C22 H22 0.9500 . ?
C23 C24 1.395(3) . ?
C24 C25 1.381(3) . ?
C24 H24 0.9500 . ?
C25 C26 1.382(3) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?
C31 C36 1.377(3) . ?
C31 C32 1.381(3) . ?
C31 I1 2.0945(19) . ?
C32 F32 1.344(2) . ?
C32 C36 1.383(3) 3_665 ?
C36 F36 1.342(2) . ?
C36 C32 1.383(3) 3_665 ?

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
C12 N11 C15 107.57(16) . . ?
C12 N11 H11 123.4(17) . . ?
C15 N11 H11 129.0(17) . . ?
N13 C12 N11 110.81(18) . . ?
N13 C12 C23 125.16(17) . . ?
N11 C12 C23 124.02(17) . . ?
C12 N13 C14 105.48(16) . . ?
C15 C14 N13 110.09(18) . . ?
C15 C14 H14 125.0 . . ?
N13 C14 H14 125.0 . . ?
C14 C15 N11 106.04(18) . . ?
C14 C15 H15 127.0 . . ?
N11 C15 H15 127.0 . . ?
C26 N21 C22 117.51(18) . . ?
C26 N21 I1 126.20(14) . . ?
C22 N21 I1 115.70(13) . . ?
N21 C22 C23 124.31(19) . . ?
N21 C22 H22 117.8 . . ?
C23 C22 H22 117.8 . . ?
C22 C23 C24 116.96(19) . . ?
C22 C23 C12 119.77(18) . . ?
C24 C23 C12 123.26(17) . . ?
C25 C24 C23 119.23(18) . . ?
C25 C24 H24 120.4 . . ?
C23 C24 H24 120.4 . . ?
C24 C25 C26 119.1(2) . . ?
C24 C25 H25 120.4 . . ?
C26 C25 H25 120.4 . . ?
N21 C26 C25 122.8(2) . . ?
N21 C26 H26 118.6 . . ?
C25 C26 H26 118.6 . . ?
C36 C31 C32 116.64(17) . . ?
C36 C31 I1 122.47(15) . . ?
C32 C31 I1 120.90(14) . . ?
C31 I1 N21 177.47(7) . . ?
F32 C32 C31 120.10(17) . . ?
F32 C32 C36 118.00(17) . 3_665 ?
C31 C32 C36 121.89(18) . 3_665 ?
F36 C36 C31 120.53(17) . . ?
F36 C36 C32 118.00(18) . 3_665 ?
C31 C36 C32 121.47(18) . 3_665 ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C15 N11 C12 N13 -0.2(2) . . . . ?
C15 N11 C12 C23 -179.74(19) . . . . ?
N11 C12 N13 C14 0.1(2) . . . . ?
C23 C12 N13 C14 179.67(19) . . . . ?
C12 N13 C14 C15 0.0(2) . . . . ?
N13 C14 C15 N11 -0.1(3) . . . . ?
C12 N11 C15 C14 0.2(2) . . . . ?
C26 N21 C22 C23 0.0(3) . . . . ?
I1 N21 C22 C23 171.68(16) . . . . ?
N21 C22 C23 C24 -0.1(3) . . . . ?
N21 C22 C23 C12 -178.9(2) . . . . ?
N13 C12 C23 C22 -12.6(3) . . . . ?
N11 C12 C23 C22 166.8(2) . . . . ?
N13 C12 C23 C24 168.7(2) . . . . ?
N11 C12 C23 C24 -11.8(3) . . . . ?
C22 C23 C24 C25 -0.1(3) . . . . ?
C12 C23 C24 C25 178.56(19) . . . . ?
C23 C24 C25 C26 0.5(3) . . . . ?
C22 N21 C26 C25 0.4(3) . . . . ?
I1 N21 C26 C25 -170.30(16) . . . . ?
C24 C25 C26 N21 -0.7(3) . . . . ?
C36 C31 C32 F32 178.81(18) . . . . ?
I1 C31 C32 F32 -1.2(3) . . . . ?
C36 C31 C32 C36 0.0(3) . . . 3_665 ?
I1 C31 C32 C36 -179.99(15) . . . 3_665 ?
C32 C31 C36 F36 -179.84(18) . . . . ?
I1 C31 C36 F36 0.2(3) . . . . ?
C32 C31 C36 C32 0.0(3) . . . 3_665 ?
I1 C31 C36 C32 179.99(15) . . . 3_665 ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N11 H11 N13 0.88(3) 1.96(3) 2.834(2) 170(2) 4_566

_diffrn_measured_fraction_theta_max 0.934
_diffrn_reflns_theta_full        30.00
_diffrn_measured_fraction_theta_full 0.983
_refine_diff_density_max         0.734
_refine_diff_density_min         -0.545
_refine_diff_density_rms         0.107
_database_code_depnum_ccdc_archive 'CCDC 994317'
#######################################################################
#
#                 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_A2D9

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
TW-1-57 [2-(3-pyridyl)-imidazole]2,  1,3,5-F3-2,4,6-I3-benzene
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         
;
(C8 H7 N3)2 (C6 F3 I3)
;
_chemical_formula_sum            'C22 H14 F3 I3 N6'
_chemical_formula_weight         800.09

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           Orthorhombic
_symmetry_space_group_name_H-M   Pbcn

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

_cell_length_a                   32.4147(16)
_cell_length_b                   9.9354(5)
_cell_length_c                   7.4776(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2408.2(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    9957
_cell_measurement_theta_min      2.51
_cell_measurement_theta_max      32.56

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.06
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.207
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1496
_exptl_absorpt_coefficient_mu    3.941
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4050
_exptl_absorpt_correction_T_max  0.7979
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      120(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            18651
_diffrn_reflns_av_R_equivalents  0.0300
_diffrn_reflns_av_sigmaI/netI    0.0260
_diffrn_reflns_limit_h_min       -46
_diffrn_reflns_limit_h_max       42
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.14
_diffrn_reflns_theta_max         32.58
_reflns_number_total             3961
_reflns_number_gt                3361
_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)+(0.0200P)²+10.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3961
_refine_ls_number_parameters     159
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0420
_refine_ls_R_factor_gt           0.0343
_refine_ls_wR_factor_ref         0.0805
_refine_ls_wR_factor_gt          0.0781
_refine_ls_goodness_of_fit_ref   1.157
_refine_ls_restrained_S_all      1.157
_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
N11 N 0.76291(8) 0.6067(3) 0.2748(4) 0.0162(5) Uani 1 1 d . . .
H11 H 0.7545(13) 0.689(4) 0.263(6) 0.019 Uiso 1 1 d . . .
C12 C 0.74088(9) 0.4963(3) 0.2268(4) 0.0146(5) Uani 1 1 d . . .
N13 N 0.76115(8) 0.3842(3) 0.2663(4) 0.0172(5) Uani 1 1 d . . .
C14 C 0.79780(10) 0.4255(3) 0.3399(5) 0.0176(6) Uani 1 1 d . . .
H14 H 0.8190 0.3670 0.3807 0.021 Uiso 1 1 calc R . .
C15 C 0.79944(10) 0.5624(3) 0.3462(5) 0.0181(6) Uani 1 1 d . . .
H15 H 0.8214 0.6161 0.3909 0.022 Uiso 1 1 calc R . .
C21 C 0.68286(10) 0.6272(3) 0.0975(5) 0.0184(6) Uani 1 1 d . . .
H21 H 0.6985 0.7064 0.1198 0.022 Uiso 1 1 calc R . .
N21 N 0.64546(9) 0.6411(3) 0.0254(4) 0.0221(6) Uani 1 1 d . . .
C23 C 0.70046(9) 0.5037(3) 0.1420(4) 0.0148(5) Uani 1 1 d . . .
C24 C 0.67770(10) 0.3890(3) 0.1037(5) 0.0198(6) Uani 1 1 d . . .
H24 H 0.6886 0.3024 0.1299 0.024 Uiso 1 1 calc R . .
C25 C 0.63899(10) 0.4017(4) 0.0268(5) 0.0224(7) Uani 1 1 d . . .
H25 H 0.6231 0.3242 -0.0015 0.027 Uiso 1 1 calc R . .
C26 C 0.62396(10) 0.5289(4) -0.0079(5) 0.0223(7) Uani 1 1 d . . .
H26 H 0.5971 0.5372 -0.0577 0.027 Uiso 1 1 calc R . .
C31 C 0.5000 1.1754(5) 0.2500 0.0211(9) Uani 1 2 d S . .
I1 I 0.5000 1.38457(4) 0.2500 0.03351(10) Uani 1 2 d S . .
C32 C 0.53401(10) 1.1032(4) 0.1928(5) 0.0199(6) Uani 1 1 d . . .
F32 F 0.56718(7) 1.1709(2) 0.1344(3) 0.0280(5) Uani 1 1 d . . .
C33 C 0.53517(9) 0.9648(4) 0.1931(4) 0.0186(6) Uani 1 1 d . . .
I2 I 0.586874(6) 0.85293(3) 0.11544(3) 0.02317(7) Uani 1 1 d . . .
C34 C 0.5000 0.8991(4) 0.2500 0.0162(8) Uani 1 2 d S . .
F34 F 0.5000 0.7632(3) 0.2500 0.0283(7) Uani 1 2 d S . .


_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
N11 C12 1.357(4) . ?
N11 C15 1.371(4) . ?
N11 H11 0.87(4) . ?
C12 N13 1.326(4) . ?
C12 C23 1.457(4) . ?
N13 C14 1.372(4) . ?
C14 C15 1.362(4) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
C21 N21 1.334(4) . ?
C21 C23 1.394(4) . ?
C21 H21 0.9500 . ?
N21 C26 1.338(5) . ?
N21 I2 2.914(3) . ?
C23 C24 1.387(4) . ?
C24 C25 1.386(5) . ?
C24 H24 0.9500 . ?
C25 C26 1.379(5) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?
C31 C32 1.383(4) 3_655 ?
C31 C32 1.383(4) . ?
C31 I1 2.078(5) . ?
C32 F32 1.341(4) . ?
C32 C33 1.376(5) . ?
C33 C34 1.381(4) . ?
C33 I2 2.093(3) . ?
C34 F34 1.351(5) . ?
C34 C33 1.381(4) 3_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
C12 N11 C15 107.3(3) . . ?
C12 N11 H11 125(3) . . ?
C15 N11 H11 128(3) . . ?
N13 C12 N11 111.0(3) . . ?
N13 C12 C23 125.8(3) . . ?
N11 C12 C23 123.2(3) . . ?
C12 N13 C14 105.5(3) . . ?
C15 C14 N13 110.3(3) . . ?
C15 C14 H14 124.9 . . ?
N13 C14 H14 124.9 . . ?
C14 C15 N11 105.8(3) . . ?
C14 C15 H15 127.1 . . ?
N11 C15 H15 127.1 . . ?
N21 C21 C23 124.0(3) . . ?
N21 C21 H21 118.0 . . ?
C23 C21 H21 118.0 . . ?
C21 N21 C26 117.5(3) . . ?
C21 N21 I2 125.0(2) . . ?
C26 N21 I2 107.8(2) . . ?
C24 C23 C21 117.1(3) . . ?
C24 C23 C12 121.8(3) . . ?
C21 C23 C12 121.1(3) . . ?
C25 C24 C23 119.5(3) . . ?
C25 C24 H24 120.3 . . ?
C23 C24 H24 120.3 . . ?
C26 C25 C24 118.8(3) . . ?
C26 C25 H25 120.6 . . ?
C24 C25 H25 120.6 . . ?
N21 C26 C25 123.0(3) . . ?
N21 C26 H26 118.5 . . ?
C25 C26 H26 118.5 . . ?
C32 C31 C32 117.6(5) 3_655 . ?
C32 C31 I1 121.2(2) 3_655 . ?
C32 C31 I1 121.2(2) . . ?
F32 C32 C33 118.7(3) . . ?
F32 C32 C31 118.7(3) . . ?
C33 C32 C31 122.6(3) . . ?
C32 C33 C34 116.8(3) . . ?
C32 C33 I2 123.5(2) . . ?
C34 C33 I2 119.7(3) . . ?
C33 I2 N21 165.82(11) . . ?
F34 C34 C33 118.2(2) . . ?
F34 C34 C33 118.2(2) . 3_655 ?
C33 C34 C33 123.6(4) . 3_655 ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C15 N11 C12 N13 0.9(4) . . . . ?
C15 N11 C12 C23 -178.6(3) . . . . ?
N11 C12 N13 C14 -0.9(4) . . . . ?
C23 C12 N13 C14 178.7(3) . . . . ?
C12 N13 C14 C15 0.5(4) . . . . ?
N13 C14 C15 N11 0.0(4) . . . . ?
C12 N11 C15 C14 -0.6(4) . . . . ?
C23 C21 N21 C26 -0.9(5) . . . . ?
C23 C21 N21 I2 140.9(3) . . . . ?
N21 C21 C23 C24 1.8(5) . . . . ?
N21 C21 C23 C12 -177.6(3) . . . . ?
N13 C12 C23 C24 4.2(5) . . . . ?
N11 C12 C23 C24 -176.3(3) . . . . ?
N13 C12 C23 C21 -176.4(3) . . . . ?
N11 C12 C23 C21 3.1(5) . . . . ?
C21 C23 C24 C25 -1.0(5) . . . . ?
C12 C23 C24 C25 178.5(3) . . . . ?
C23 C24 C25 C26 -0.6(5) . . . . ?
C21 N21 C26 C25 -0.9(5) . . . . ?
I2 N21 C26 C25 -148.7(3) . . . . ?
C24 C25 C26 N21 1.6(6) . . . . ?
C32 C31 C32 F32 179.1(4) 3_655 . . . ?
I1 C31 C32 F32 -0.9(4) . . . . ?
C32 C31 C32 C33 -0.8(2) 3_655 . . . ?
I1 C31 C32 C33 179.2(2) . . . . ?
F32 C32 C33 C34 -178.4(3) . . . . ?
C31 C32 C33 C34 1.5(5) . . . . ?
F32 C32 C33 I2 2.2(5) . . . . ?
C31 C32 C33 I2 -177.9(2) . . . . ?
C32 C33 C34 F34 179.3(2) . . . . ?
I2 C33 C34 F34 -1.3(3) . . . . ?
C32 C33 C34 C33 -0.7(2) . . . 3_655 ?
I2 C33 C34 C33 178.7(3) . . . 3_655 ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N11 H11 N13 0.87(4) 2.00(4) 2.866(4) 173(4) 8_765

_diffrn_measured_fraction_theta_max 0.902
_diffrn_reflns_theta_full        30.00
_diffrn_measured_fraction_theta_full 0.988
_refine_diff_density_max         1.906
_refine_diff_density_min         -0.858
_refine_diff_density_rms         0.139
_database_code_depnum_ccdc_archive 'CCDC 994318'
#######################################################################
#
#                 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_A2D10

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
TW-1-67 [2-(3-pyridyl)-imidazole], 4,4'-diiodo-F8-biphenyl
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         
;
(C8 H7 N3)2 (C12 F8 I2)
;
_chemical_formula_sum            'C28 H14 F8 I2 N6'
_chemical_formula_weight         840.25

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   Pc

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

_cell_length_a                   4.2333(3)
_cell_length_b                   32.768(2)
_cell_length_c                   9.9627(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 93.7600(10)
_cell_angle_gamma                90.00
_cell_volume                     1379.00(18)
_cell_formula_units_Z            2
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    9940
_cell_measurement_theta_min      5.40
_cell_measurement_theta_max      30.91

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.024
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             804
_exptl_absorpt_coefficient_mu    2.367
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5570
_exptl_absorpt_correction_T_max  0.7643
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      120(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            15349
_diffrn_reflns_av_R_equivalents  0.0178
_diffrn_reflns_av_sigmaI/netI    0.0266
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -42
_diffrn_reflns_limit_k_max       46
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         5.40
_diffrn_reflns_theta_max         30.97
_reflns_number_total             7025
_reflns_number_gt                6767
_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)+(0.0200P)²+0.7000P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.129(11)
_refine_ls_number_reflns         7025
_refine_ls_number_parameters     400
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0216
_refine_ls_R_factor_gt           0.0205
_refine_ls_wR_factor_ref         0.0480
_refine_ls_wR_factor_gt          0.0475
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_restrained_S_all      1.027
_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
N11A N 0.3340(6) -0.01011(7) -0.4380(3) 0.0204(5) Uani 0.64(6) 1 d P A 1
H11 H 0.3687 -0.0028 -0.5208 0.024 Uiso 0.64(6) 1 calc PR A 1
N11B N 0.3340(6) -0.01011(7) -0.4380(3) 0.0204(5) Uani 0.36(6) 1 d P A 2
C12 C 0.4260(7) 0.01012(8) -0.3245(3) 0.0169(5) Uani 1 1 d . . .
N13A N 0.3297(7) -0.00955(7) -0.2157(3) 0.0226(5) Uani 0.64(6) 1 d P A 1
N13B N 0.3297(7) -0.00955(7) -0.2157(3) 0.0226(5) Uani 0.36(6) 1 d P A 2
H13 H 0.3608 -0.0019 -0.1312 0.027 Uiso 0.36(6) 1 calc PR A 2
C14 C 0.1729(8) -0.04405(9) -0.2629(3) 0.0252(7) Uani 1 1 d . . .
H14 H 0.0793 -0.0641 -0.2094 0.030 Uiso 1 1 calc R A 1
C15 C 0.1754(8) -0.04436(9) -0.3995(3) 0.0238(6) Uani 1 1 d . A .
H15 H 0.0836 -0.0647 -0.4579 0.029 Uiso 1 1 calc R B 1
N21 N 0.8286(7) 0.10391(8) -0.1859(3) 0.0238(5) Uani 1 1 d . A .
C22 C 0.6642(8) 0.06885(9) -0.1983(3) 0.0215(6) Uani 1 1 d . . .
H22 H 0.5838 0.0575 -0.1197 0.026 Uiso 1 1 calc R A .
C23 C 0.6046(7) 0.04811(8) -0.3197(3) 0.0160(5) Uani 1 1 d . A .
C24 C 0.7208(8) 0.06562(8) -0.4336(3) 0.0210(5) Uani 1 1 d . . .
H24 H 0.6831 0.0530 -0.5190 0.025 Uiso 1 1 calc R A .
C25 C 0.8917(8) 0.10160(9) -0.4217(3) 0.0230(5) Uani 1 1 d . A .
H25 H 0.9750 0.1137 -0.4984 0.028 Uiso 1 1 calc R . .
C26 C 0.9397(7) 0.11966(8) -0.2964(3) 0.0216(5) Uani 1 1 d . . .
H26 H 1.0570 0.1444 -0.2891 0.026 Uiso 1 1 calc R A .
N31A N 0.5432(6) 0.51196(7) 1.4074(2) 0.0189(5) Uani 0.33(6) 1 d P C 1
H31 H 0.5042 0.5048 1.4899 0.023 Uiso 0.33(6) 1 calc PR C 1
N31B N 0.5432(6) 0.51196(7) 1.4074(2) 0.0189(5) Uani 0.67(6) 1 d P C 2
C32 C 0.4484(7) 0.49228(8) 1.2939(3) 0.0180(5) Uani 1 1 d . . .
N33A N 0.5508(7) 0.51158(7) 1.1854(3) 0.0207(5) Uani 0.33(6) 1 d P C 1
N33B N 0.5508(7) 0.51158(7) 1.1854(3) 0.0207(5) Uani 0.67(6) 1 d P C 2
H33 H 0.5181 0.5043 1.1006 0.025 Uiso 0.67(6) 1 calc PR C 2
C34 C 0.7171(8) 0.54511(9) 1.2345(3) 0.0253(7) Uani 1 1 d . . .
H34 H 0.8181 0.5648 1.1818 0.030 Uiso 1 1 calc R C 1
C35 C 0.7132(8) 0.54549(9) 1.3703(3) 0.0223(6) Uani 1 1 d . C .
H35 H 0.8102 0.5653 1.4293 0.027 Uiso 1 1 calc R D 1
N41 N 0.0647(7) 0.39684(8) 1.1613(3) 0.0237(5) Uani 1 1 d . C .
C42 C 0.2283(8) 0.43156(9) 1.1727(3) 0.0222(6) Uani 1 1 d . . .
H42 H 0.3293 0.4409 1.0961 0.027 Uiso 1 1 calc R C .
C43 C 0.2611(6) 0.45497(8) 1.2889(3) 0.0158(5) Uani 1 1 d . C .
C44 C 0.1112(7) 0.44053(8) 1.4003(3) 0.0192(5) Uani 1 1 d . . .
H44 H 0.1282 0.4552 1.4827 0.023 Uiso 1 1 calc R C .
C45 C -0.0617(7) 0.40481(9) 1.3901(3) 0.0220(5) Uani 1 1 d . C .
H45 H -0.1668 0.3948 1.4647 0.026 Uiso 1 1 calc R . .
C46 C -0.0791(7) 0.38384(8) 1.2684(3) 0.0208(5) Uani 1 1 d . . .
H46 H -0.1982 0.3593 1.2614 0.025 Uiso 1 1 calc R C .
C51 C 0.6957(7) 0.18848(8) 0.2169(3) 0.0158(5) Uani 1 1 d . A .
I1 I 0.75740(2) 0.152213(5) 0.047627(14) 0.01763(5) Uani 1 1 d . . .
C52 C 0.8359(6) 0.22644(8) 0.2316(3) 0.0166(5) Uani 1 1 d . . .
F52 F 1.0232(4) 0.24053(5) 0.13864(16) 0.0224(3) Uani 1 1 d . A .
C53 C 0.7957(6) 0.25066(8) 0.3431(3) 0.0178(5) Uani 1 1 d . A .
F53 F 0.9516(4) 0.28609(5) 0.35231(17) 0.0224(3) Uani 1 1 d . . .
C54 C 0.6087(7) 0.23878(8) 0.4453(3) 0.0166(5) Uani 1 1 d . . .
C55 C 0.4628(7) 0.20058(9) 0.4288(3) 0.0181(6) Uani 1 1 d . A .
F55 F 0.2637(4) 0.18735(5) 0.51925(15) 0.0226(3) Uani 1 1 d . . .
C56 C 0.5107(7) 0.17608(8) 0.3191(3) 0.0162(5) Uani 1 1 d . . .
F56 F 0.3671(4) 0.13931(5) 0.31354(16) 0.0228(3) Uani 1 1 d . A .
C61 C 0.3947(8) 0.31152(9) 0.7900(3) 0.0194(6) Uani 1 1 d . A .
I2 I 0.24235(3) 0.345785(5) 0.952028(16) 0.02037(5) Uani 1 1 d . . .
C62 C 0.4862(7) 0.27117(8) 0.8035(3) 0.0224(5) Uani 1 1 d . . .
F62 F 0.4972(5) 0.25307(5) 0.92493(16) 0.0327(4) Uani 1 1 d . C .
C63 C 0.5690(7) 0.24860(8) 0.6946(3) 0.0218(5) Uani 1 1 d . A .
F63 F 0.6676(5) 0.21003(5) 0.71522(17) 0.0311(4) Uani 1 1 d . . .
C64 C 0.5528(7) 0.26474(8) 0.5641(3) 0.0168(5) Uani 1 1 d . A .
C65 C 0.4741(7) 0.30577(9) 0.5534(3) 0.0171(5) Uani 1 1 d . . .
F65 F 0.4607(4) 0.32457(4) 0.43309(15) 0.0197(3) Uani 1 1 d . A .
C66 C 0.3956(7) 0.32830(8) 0.6635(3) 0.0185(6) Uani 1 1 d . A .
F66 F 0.3138(5) 0.36774(4) 0.64288(18) 0.0259(4) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N11A C12 1.346(3) . ?
N11A C15 1.375(4) . ?
N11A H11 0.8800 . ?
C12 N13A 1.347(4) . ?
C12 C23 1.456(4) . ?
N13A C14 1.378(4) . ?
C14 C15 1.362(5) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
N21 C26 1.329(4) . ?
N21 C22 1.345(4) . ?
N21 I1 2.846(3) . ?
C22 C23 1.395(4) . ?
C22 H22 0.9500 . ?
C23 C24 1.390(3) . ?
C24 C25 1.384(4) . ?
C24 H24 0.9500 . ?
C25 C26 1.384(4) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?
N31A C32 1.341(4) . ?
N31A C35 1.377(4) . ?
N31A H31 0.8800 . ?
C32 N33A 1.349(4) . ?
C32 C43 1.456(4) . ?
N33A C34 1.378(4) . ?
C34 C35 1.354(5) . ?
C34 H34 0.9500 . ?
C35 H35 0.9500 . ?
N41 C42 1.333(4) . ?
N41 C46 1.333(4) . ?
N41 I2 2.813(3) . ?
C42 C43 1.389(4) . ?
C42 H42 0.9500 . ?
C43 C44 1.397(4) . ?
C44 C45 1.381(4) . ?
C44 H44 0.9500 . ?
C45 C46 1.391(4) . ?
C45 H45 0.9500 . ?
C46 H46 0.9500 . ?
C51 C52 1.382(4) . ?
C51 C56 1.385(4) . ?
C51 I1 2.093(3) . ?
C52 F52 1.340(3) . ?
C52 C53 1.385(3) . ?
C53 F53 1.336(3) . ?
C53 C54 1.386(4) . ?
C54 C55 1.400(4) . ?
C54 C64 1.489(3) . ?
C55 F55 1.346(3) . ?
C55 C56 1.382(4) . ?
C56 F56 1.349(3) . ?
C61 C66 1.375(4) . ?
C61 C62 1.382(4) . ?
C61 I2 2.102(3) . ?
C62 F62 1.346(3) . ?
C62 C63 1.377(4) . ?
C63 F63 1.342(3) . ?
C63 C64 1.402(4) . ?
C64 C65 1.387(4) . ?
C65 F65 1.345(3) . ?
C65 C66 1.381(4) . ?
C66 F66 1.350(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
C12 N11A C15 106.7(2) . . ?
C12 N11A H11 126.7 . . ?
C15 N11A H11 126.7 . . ?
N11A C12 N13A 110.7(2) . . ?
N11A C12 C23 124.7(2) . . ?
N13A C12 C23 124.5(2) . . ?
C12 N13A C14 106.4(2) . . ?
C15 C14 N13A 108.2(3) . . ?
C15 C14 H14 125.9 . . ?
N13A C14 H14 125.9 . . ?
C14 C15 N11A 108.0(3) . . ?
C14 C15 H15 126.0 . . ?
N11A C15 H15 126.0 . . ?
C26 N21 C22 117.7(3) . . ?
C26 N21 I1 121.56(18) . . ?
C22 N21 I1 117.94(19) . . ?
N21 C22 C23 124.0(3) . . ?
N21 C22 H22 118.0 . . ?
C23 C22 H22 118.0 . . ?
C24 C23 C22 116.9(2) . . ?
C24 C23 C12 122.5(2) . . ?
C22 C23 C12 120.6(2) . . ?
C25 C24 C23 119.5(2) . . ?
C25 C24 H24 120.2 . . ?
C23 C24 H24 120.2 . . ?
C26 C25 C24 119.1(3) . . ?
C26 C25 H25 120.5 . . ?
C24 C25 H25 120.5 . . ?
N21 C26 C25 122.8(3) . . ?
N21 C26 H26 118.6 . . ?
C25 C26 H26 118.6 . . ?
C32 N31A C35 106.9(2) . . ?
C32 N31A H31 126.6 . . ?
C35 N31A H31 126.6 . . ?
N31A C32 N33A 110.9(2) . . ?
N31A C32 C43 124.4(2) . . ?
N33A C32 C43 124.7(2) . . ?
C32 N33A C34 105.8(2) . . ?
C35 C34 N33A 108.8(3) . . ?
C35 C34 H34 125.6 . . ?
N33A C34 H34 125.6 . . ?
C34 C35 N31A 107.6(3) . . ?
C34 C35 H35 126.2 . . ?
N31A C35 H35 126.2 . . ?
C42 N41 C46 117.8(3) . . ?
C42 N41 I2 114.1(2) . . ?
C46 N41 I2 124.17(19) . . ?
N41 C42 C43 124.4(3) . . ?
N41 C42 H42 117.8 . . ?
C43 C42 H42 117.8 . . ?
C42 C43 C44 116.7(2) . . ?
C42 C43 C32 121.1(3) . . ?
C44 C43 C32 122.2(2) . . ?
C45 C44 C43 119.6(2) . . ?
C45 C44 H44 120.2 . . ?
C43 C44 H44 120.2 . . ?
C44 C45 C46 118.7(3) . . ?
C44 C45 H45 120.6 . . ?
C46 C45 H45 120.6 . . ?
N41 C46 C45 122.6(3) . . ?
N41 C46 H46 118.7 . . ?
C45 C46 H46 118.7 . . ?
C52 C51 C56 116.5(3) . . ?
C52 C51 I1 121.4(2) . . ?
C56 C51 I1 122.1(2) . . ?
C51 I1 N21 178.60(10) . . ?
F52 C52 C51 120.5(2) . . ?
F52 C52 C53 117.8(2) . . ?
C51 C52 C53 121.7(2) . . ?
F53 C53 C52 117.8(2) . . ?
F53 C53 C54 119.8(2) . . ?
C52 C53 C54 122.3(2) . . ?
C53 C54 C55 115.7(2) . . ?
C53 C54 C64 123.5(2) . . ?
C55 C54 C64 120.8(3) . . ?
F55 C55 C56 118.2(3) . . ?
F55 C55 C54 120.0(2) . . ?
C56 C55 C54 121.7(3) . . ?
F56 C56 C55 117.5(3) . . ?
F56 C56 C51 120.4(2) . . ?
C55 C56 C51 122.0(3) . . ?
C66 C61 C62 117.0(3) . . ?
C66 C61 I2 120.6(2) . . ?
C62 C61 I2 122.3(2) . . ?
C61 I2 N41 175.53(11) . . ?
F62 C62 C63 118.4(2) . . ?
F62 C62 C61 120.1(2) . . ?
C63 C62 C61 121.4(3) . . ?
F63 C63 C62 118.6(2) . . ?
F63 C63 C64 119.5(2) . . ?
C62 C63 C64 121.9(2) . . ?
C65 C64 C63 115.7(2) . . ?
C65 C64 C54 122.9(2) . . ?
C63 C64 C54 121.4(2) . . ?
F65 C65 C66 117.7(2) . . ?
F65 C65 C64 120.5(2) . . ?
C66 C65 C64 121.7(3) . . ?
F66 C66 C61 120.4(2) . . ?
F66 C66 C65 117.6(3) . . ?
C61 C66 C65 122.0(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C15 N11A C12 N13A -0.7(3) . . . . ?
C15 N11A C12 C23 179.4(3) . . . . ?
N11A C12 N13A C14 0.7(3) . . . . ?
C23 C12 N13A C14 -179.4(3) . . . . ?
C12 N13A C14 C15 -0.5(4) . . . . ?
N13A C14 C15 N11A 0.1(4) . . . . ?
C12 N11A C15 C14 0.3(3) . . . . ?
C26 N21 C22 C23 0.2(5) . . . . ?
I1 N21 C22 C23 161.4(2) . . . . ?
N21 C22 C23 C24 -0.9(5) . . . . ?
N21 C22 C23 C12 179.6(3) . . . . ?
N11A C12 C23 C24 -5.4(5) . . . . ?
N13A C12 C23 C24 174.7(3) . . . . ?
N11A C12 C23 C22 174.0(3) . . . . ?
N13A C12 C23 C22 -5.8(4) . . . . ?
C22 C23 C24 C25 1.2(4) . . . . ?
C12 C23 C24 C25 -179.3(3) . . . . ?
C23 C24 C25 C26 -0.8(5) . . . . ?
C22 N21 C26 C25 0.2(5) . . . . ?
I1 N21 C26 C25 -160.3(2) . . . . ?
C24 C25 C26 N21 0.1(5) . . . . ?
C35 N31A C32 N33A 0.2(3) . . . . ?
C35 N31A C32 C43 180.0(3) . . . . ?
N31A C32 N33A C34 -0.2(3) . . . . ?
C43 C32 N33A C34 -180.0(3) . . . . ?
C32 N33A C34 C35 0.1(4) . . . . ?
N33A C34 C35 N31A 0.0(4) . . . . ?
C32 N31A C35 C34 -0.1(3) . . . . ?
C46 N41 C42 C43 0.5(5) . . . . ?
I2 N41 C42 C43 -158.2(2) . . . . ?
N41 C42 C43 C44 0.2(5) . . . . ?
N41 C42 C43 C32 179.0(3) . . . . ?
N31A C32 C43 C42 -166.1(3) . . . . ?
N33A C32 C43 C42 13.6(4) . . . . ?
N31A C32 C43 C44 12.7(4) . . . . ?
N33A C32 C43 C44 -167.6(3) . . . . ?
C42 C43 C44 C45 -0.8(4) . . . . ?
C32 C43 C44 C45 -179.6(3) . . . . ?
C43 C44 C45 C46 0.7(4) . . . . ?
C42 N41 C46 C45 -0.6(5) . . . . ?
I2 N41 C46 C45 155.7(2) . . . . ?
C44 C45 C46 N41 0.0(5) . . . . ?
C56 C51 C52 F52 178.8(2) . . . . ?
I1 C51 C52 F52 -1.8(4) . . . . ?
C56 C51 C52 C53 0.5(4) . . . . ?
I1 C51 C52 C53 179.9(2) . . . . ?
F52 C52 C53 F53 -1.4(4) . . . . ?
C51 C52 C53 F53 176.9(3) . . . . ?
F52 C52 C53 C54 -179.6(2) . . . . ?
C51 C52 C53 C54 -1.2(4) . . . . ?
F53 C53 C54 C55 -178.0(3) . . . . ?
C52 C53 C54 C55 0.1(4) . . . . ?
F53 C53 C54 C64 4.0(4) . . . . ?
C52 C53 C54 C64 -177.9(3) . . . . ?
C53 C54 C55 F55 -176.5(3) . . . . ?
C64 C54 C55 F55 1.6(4) . . . . ?
C53 C54 C55 C56 1.7(4) . . . . ?
C64 C54 C55 C56 179.8(3) . . . . ?
F55 C55 C56 F56 -3.5(4) . . . . ?
C54 C55 C56 F56 178.2(3) . . . . ?
F55 C55 C56 C51 175.8(3) . . . . ?
C54 C55 C56 C51 -2.4(5) . . . . ?
C52 C51 C56 F56 -179.4(2) . . . . ?
I1 C51 C56 F56 1.3(4) . . . . ?
C52 C51 C56 C55 1.2(4) . . . . ?
I1 C51 C56 C55 -178.1(2) . . . . ?
C66 C61 C62 F62 178.6(3) . . . . ?
I2 C61 C62 F62 -3.8(4) . . . . ?
C66 C61 C62 C63 -1.2(5) . . . . ?
I2 C61 C62 C63 176.5(2) . . . . ?
F62 C62 C63 F63 -2.3(5) . . . . ?
C61 C62 C63 F63 177.5(3) . . . . ?
F62 C62 C63 C64 177.6(3) . . . . ?
C61 C62 C63 C64 -2.6(5) . . . . ?
F63 C63 C64 C65 -174.8(3) . . . . ?
C62 C63 C64 C65 5.2(4) . . . . ?
F63 C63 C64 C54 6.7(5) . . . . ?
C62 C63 C64 C54 -173.2(3) . . . . ?
C53 C54 C64 C65 46.5(5) . . . . ?
C55 C54 C64 C65 -131.4(3) . . . . ?
C53 C54 C64 C63 -135.2(3) . . . . ?
C55 C54 C64 C63 46.9(4) . . . . ?
C63 C64 C65 F65 178.1(3) . . . . ?
C54 C64 C65 F65 -3.4(4) . . . . ?
C63 C64 C65 C66 -4.3(4) . . . . ?
C54 C64 C65 C66 174.1(3) . . . . ?
C62 C61 C66 F66 -179.0(3) . . . . ?
I2 C61 C66 F66 3.4(4) . . . . ?
C62 C61 C66 C65 2.1(5) . . . . ?
I2 C61 C66 C65 -175.6(2) . . . . ?
F65 C65 C66 F66 -0.6(4) . . . . ?
C64 C65 C66 F66 -178.2(3) . . . . ?
F65 C65 C66 C61 178.4(3) . . . . ?
C64 C65 C66 C61 0.8(5) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N11A H11 N13A 0.88 1.98 2.839(4) 165.1 2_554
N13B H13 N11B 0.88 1.97 2.839(4) 167.0 2
N31A H31 N33A 0.88 2.02 2.872(3) 163.6 2_565
N33B H33 N31B 0.88 2.01 2.872(3) 167.9 2_564

_diffrn_measured_fraction_theta_max 0.929
_diffrn_reflns_theta_full        27.50
_diffrn_measured_fraction_theta_full 0.978
_refine_diff_density_max         0.625
_refine_diff_density_min         -0.414
_refine_diff_density_rms         0.077
_database_code_depnum_ccdc_archive 'CCDC 994319'
#######################################################################
#
#                 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_A2D14

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
TW-1-47 [2-(3-pyridyl)-imidazole]2, 1-bromo-4-iodotetrafluorobenzene
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         
;
(C8 H7 N3)2 (C6 Br F4 I)
;
_chemical_formula_sum            'C22 H14 Br F4 I N6'
_chemical_formula_weight         645.20

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'
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   P2(1)/c

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

_cell_length_a                   4.0019(11)
_cell_length_b                   28.546(8)
_cell_length_c                   9.972(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 98.464(8)
_cell_angle_gamma                90.00
_cell_volume                     1126.7(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    8237
_cell_measurement_theta_min      2.51
_cell_measurement_theta_max      29.51

_exptl_crystal_description       rod
_exptl_crystal_colour            colourless
_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    1.902
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             624
_exptl_absorpt_coefficient_mu    3.251
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4853
_exptl_absorpt_correction_T_max  0.8288
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      120(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            14624
_diffrn_reflns_av_R_equivalents  0.2400
_diffrn_reflns_av_sigmaI/netI    0.1152
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -37
_diffrn_reflns_limit_k_max       39
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.18
_diffrn_reflns_theta_max         29.61
_reflns_number_total             3088
_reflns_number_gt                2657
_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)+(0.0300P)²+20.0000P] 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         3088
_refine_ls_number_parameters     155
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1276
_refine_ls_R_factor_gt           0.1103
_refine_ls_wR_factor_ref         0.2432
_refine_ls_wR_factor_gt          0.2375
_refine_ls_goodness_of_fit_ref   1.348
_refine_ls_restrained_S_all      1.348
_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
N11A N 0.284(2) 0.2407(3) -0.0120(9) 0.0268(17) Uani 0.2(2) 1 d P A 1
H11 H 0.3211 0.2510 0.0720 0.032 Uiso 0.2(2) 1 calc PR A 1
N11B N 0.284(2) 0.2407(3) -0.0120(9) 0.0268(17) Uani 0.8(2) 1 d P A 2
C12 C 0.361(2) 0.2618(3) -0.1214(10) 0.0237(18) Uani 1 1 d . . .
N13A N 0.269(2) 0.2359(3) -0.2341(8) 0.0228(15) Uani 0.2(2) 1 d P A 1
N13B N 0.269(2) 0.2359(3) -0.2341(8) 0.0228(15) Uani 0.8(2) 1 d P A 2
H13 H 0.2977 0.2433 -0.3173 0.027 Uiso 0.8(2) 1 calc PR A 2
C14 C 0.121(3) 0.1955(3) -0.1938(10) 0.0273(19) Uani 1 1 d . . .
H14 H 0.0299 0.1703 -0.2499 0.033 Uiso 1 1 calc R A 1
C15 C 0.132(3) 0.1992(4) -0.0571(10) 0.0263(18) Uani 1 1 d . A .
H15 H 0.0472 0.1765 -0.0011 0.032 Uiso 1 1 calc R B 1
N21 N 0.710(2) 0.3771(3) 0.0022(9) 0.0309(18) Uani 1 1 d . . .
C22 C 0.568(3) 0.3354(4) -0.0065(11) 0.029(2) Uani 1 1 d . A .
H22 H 0.4858 0.3235 0.0714 0.035 Uiso 1 1 calc R . .
C23 C 0.529(2) 0.3072(3) -0.1242(9) 0.0217(17) Uani 1 1 d . A .
C24 C 0.652(2) 0.3247(3) -0.2372(10) 0.0244(18) Uani 1 1 d . . .
H24 H 0.6316 0.3072 -0.3189 0.029 Uiso 1 1 calc R A .
C25 C 0.805(2) 0.3688(4) -0.2281(10) 0.0266(19) Uani 1 1 d . A .
H25 H 0.8938 0.3813 -0.3035 0.032 Uiso 1 1 calc R . .
C26 C 0.826(2) 0.3940(4) -0.1086(11) 0.028(2) Uani 1 1 d . A .
H26 H 0.9254 0.4243 -0.1045 0.034 Uiso 1 1 calc R . .
I1 I 0.6188(2) 0.43337(3) 0.22506(8) 0.0277(2) Uani 0.50 1 d P C 1
Br1 Br 0.6188(2) 0.43337(3) 0.22506(8) 0.0277(2) Uani 0.50 1 d P C 2
C51 C 0.544(2) 0.4726(4) 0.3866(9) 0.0240(18) Uani 1 1 d . . .
C52 C 0.413(2) 0.4538(3) 0.4948(11) 0.0255(18) Uani 1 1 d . . .
C56 C 0.633(2) 0.5190(4) 0.3953(10) 0.0252(18) Uani 1 1 d . . .
F52 F 0.3167(17) 0.4085(2) 0.4940(7) 0.0354(14) Uani 1 1 d . . .
F56 F 0.7752(18) 0.5392(2) 0.2939(7) 0.0363(15) 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
N11A C12 1.322(12) . ?
N11A C15 1.374(13) . ?
N11A H11 0.8800 . ?
C12 N13A 1.351(12) . ?
C12 C23 1.464(13) . ?
N13A C14 1.383(13) . ?
C14 C15 1.361(13) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
N21 C22 1.317(14) . ?
N21 C26 1.349(14) . ?
N21 I1 2.808(9) . ?
C22 C23 1.413(13) . ?
C22 H22 0.9500 . ?
C23 C24 1.385(12) . ?
C24 C25 1.395(14) . ?
C24 H24 0.9500 . ?
C25 C26 1.384(14) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?
I1 C51 2.020(9) . ?
C51 C56 1.370(14) . ?
C51 C52 1.377(13) . ?
C52 F52 1.348(11) . ?
C52 C56 1.378(14) 3_666 ?
C56 F56 1.359(11) . ?
C56 C52 1.378(14) 3_666 ?

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
C12 N11A C15 105.6(8) . . ?
C12 N11A H11 127.2 . . ?
C15 N11A H11 127.2 . . ?
N11A C12 N13A 111.6(8) . . ?
N11A C12 C23 125.8(9) . . ?
N13A C12 C23 122.6(8) . . ?
C12 N13A C14 106.9(8) . . ?
C15 C14 N13A 105.9(9) . . ?
C15 C14 H14 127.0 . . ?
N13A C14 H14 127.0 . . ?
C14 C15 N11A 110.0(9) . . ?
C14 C15 H15 125.0 . . ?
N11A C15 H15 125.0 . . ?
C22 N21 C26 117.8(9) . . ?
C22 N21 I1 117.7(7) . . ?
C26 N21 I1 123.0(7) . . ?
N21 C22 C23 124.3(9) . . ?
N21 C22 H22 117.9 . . ?
C23 C22 H22 117.9 . . ?
C24 C23 C22 117.5(9) . . ?
C24 C23 C12 123.6(9) . . ?
C22 C23 C12 118.9(8) . . ?
C23 C24 C25 118.4(9) . . ?
C23 C24 H24 120.8 . . ?
C25 C24 H24 120.8 . . ?
C26 C25 C24 119.7(9) . . ?
C26 C25 H25 120.1 . . ?
C24 C25 H25 120.1 . . ?
N21 C26 C25 122.3(9) . . ?
N21 C26 H26 118.8 . . ?
C25 C26 H26 118.8 . . ?
C51 I1 N21 178.5(3) . . ?
C56 C51 C52 117.0(9) . . ?
C56 C51 I1 121.2(7) . . ?
C52 C51 I1 121.8(8) . . ?
F52 C52 C51 120.7(9) . . ?
F52 C52 C56 118.3(9) . 3_666 ?
C51 C52 C56 120.9(9) . 3_666 ?
F56 C56 C51 119.8(9) . . ?
F56 C56 C52 118.1(9) . 3_666 ?
C51 C56 C52 122.1(9) . 3_666 ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C15 N11A C12 N13A -0.4(11) . . . . ?
C15 N11A C12 C23 -179.7(9) . . . . ?
N11A C12 N13A C14 0.2(11) . . . . ?
C23 C12 N13A C14 179.7(9) . . . . ?
C12 N13A C14 C15 0.0(11) . . . . ?
N13A C14 C15 N11A -0.2(12) . . . . ?
C12 N11A C15 C14 0.3(12) . . . . ?
C26 N21 C22 C23 0.1(16) . . . . ?
I1 N21 C22 C23 166.2(8) . . . . ?
N21 C22 C23 C24 0.4(16) . . . . ?
N21 C22 C23 C12 -178.9(10) . . . . ?
N11A C12 C23 C24 169.8(10) . . . . ?
N13A C12 C23 C24 -9.5(15) . . . . ?
N11A C12 C23 C22 -10.9(15) . . . . ?
N13A C12 C23 C22 169.8(9) . . . . ?
C22 C23 C24 C25 0.1(14) . . . . ?
C12 C23 C24 C25 179.4(9) . . . . ?
C23 C24 C25 C26 -1.0(14) . . . . ?
C22 N21 C26 C25 -1.1(16) . . . . ?
I1 N21 C26 C25 -166.4(7) . . . . ?
C24 C25 C26 N21 1.6(15) . . . . ?
C56 C51 C52 F52 179.6(8) . . . . ?
I1 C51 C52 F52 -2.7(13) . . . . ?
C56 C51 C52 C56 1.6(16) . . . 3_666 ?
I1 C51 C52 C56 179.4(7) . . . 3_666 ?
C52 C51 C56 F56 177.7(9) . . . . ?
I1 C51 C56 F56 -0.1(13) . . . . ?
C52 C51 C56 C52 -1.7(16) . . . 3_666 ?
I1 C51 C56 C52 -179.4(7) . . . 3_666 ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N11A H11 N13A 0.88 2.01 2.860(11) 162.0 4_566
N13B H13 N11B 0.88 1.99 2.860(11) 171.0 4_565

_diffrn_measured_fraction_theta_max 0.970
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.991
_refine_diff_density_max         1.180
_refine_diff_density_min         -1.820
_refine_diff_density_rms         0.211
_database_code_depnum_ccdc_archive 'CCDC 994320'
#######################################################################
#
#                 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_A3D3

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
TW-2-13 [2-(2-pyridyl)-imidazole]3, I-(CF2)6-I
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         
;
(C8 H7 N3)3 (C6 F12 I2)
;
_chemical_formula_sum            'C30 H21 F12 I2 N9'
_chemical_formula_weight         989.36

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.3257 6.8362 '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                   5.1393(6)
_cell_length_b                   11.0259(12)
_cell_length_c                   15.2795(17)
_cell_angle_alpha                92.084(3)
_cell_angle_beta                 91.221(3)
_cell_angle_gamma                100.093(3)
_cell_volume                     851.52(17)
_cell_formula_units_Z            1
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    9751
_cell_measurement_theta_min      2.90
_cell_measurement_theta_max      68.98

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.929
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             478
_exptl_absorpt_coefficient_mu    15.460
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.1321
_exptl_absorpt_correction_T_max  0.3710
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\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            13661
_diffrn_reflns_av_R_equivalents  0.0462
_diffrn_reflns_av_sigmaI/netI    0.0343
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.90
_diffrn_reflns_theta_max         69.25
_reflns_number_total             2928
_reflns_number_gt                2797
_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)+(0.0800P)²+1.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0033(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2928
_refine_ls_number_parameters     252
_refine_ls_number_restraints     99
_refine_ls_R_factor_all          0.0391
_refine_ls_R_factor_gt           0.0368
_refine_ls_wR_factor_ref         0.1302
_refine_ls_wR_factor_gt          0.1201
_refine_ls_goodness_of_fit_ref   1.257
_refine_ls_restrained_S_all      1.241
_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
N11 N 0.6498(10) 0.6715(4) 0.0829(3) 0.0259(10) Uani 1 1 d D . .
H11 H 0.6586 0.7428 0.0580 0.031 Uiso 1 1 calc R . .
C12 C 0.5016(10) 0.6328(5) 0.1524(3) 0.0244(11) Uani 1 1 d D . .
N13 N 0.5324(12) 0.5213(4) 0.1729(3) 0.0360(12) Uani 1 1 d D . .
C14 C 0.7090(17) 0.4875(6) 0.1148(4) 0.0476(18) Uani 1 1 d D . .
H14 H 0.7708 0.4111 0.1138 0.057 Uiso 1 1 calc R . .
C15 C 0.7822(16) 0.5794(6) 0.0592(4) 0.0431(16) Uani 1 1 d D . .
H15 H 0.9022 0.5796 0.0127 0.052 Uiso 1 1 calc R . .
C21 C 0.3348(10) 0.7099(5) 0.1955(3) 0.0251(11) Uani 1 1 d D . .
N22 N 0.3619(9) 0.8275(4) 0.1698(3) 0.0253(9) Uani 1 1 d D . .
C23 C 0.2065(11) 0.8991(5) 0.2079(3) 0.0309(12) Uani 1 1 d D . .
H23 H 0.2223 0.9819 0.1905 0.037 Uiso 1 1 calc R . .
C24 C 0.0257(12) 0.8597(6) 0.2709(4) 0.0355(13) Uani 1 1 d D . .
H24 H -0.0803 0.9138 0.2957 0.043 Uiso 1 1 calc R . .
C25 C 0.0027(11) 0.7399(6) 0.2967(4) 0.0348(13) Uani 1 1 d D . .
H25 H -0.1188 0.7103 0.3403 0.042 Uiso 1 1 calc R . .
C26 C 0.1557(11) 0.6642(5) 0.2592(4) 0.0302(12) Uani 1 1 d D . .
H26 H 0.1410 0.5813 0.2762 0.036 Uiso 1 1 calc R . .
N31 N 1.197(2) 0.9693(11) -0.0976(7) 0.0213(8) Uani 0.50 1 d PDU A -1
H31 H 1.3248 1.0330 -0.1026 0.026 Uiso 0.50 1 calc PR A -1
C32 C 1.013(2) 0.9532(9) -0.0351(7) 0.0198(6) Uani 0.50 1 d PDU A -1
N33 N 0.8461(17) 0.8523(9) -0.0489(6) 0.0200(7) Uani 0.50 1 d PDU A -1
C34 C 0.9270(19) 0.7959(9) -0.1222(6) 0.0216(8) Uani 0.50 1 d PDU A -1
H34 H 0.8424 0.7190 -0.1480 0.026 Uiso 0.50 1 calc PR A -1
C35 C 1.1419(11) 0.8654(6) -0.1515(4) 0.0220(8) Uani 0.50 1 d PDU A -1
H35 H 1.2396 0.8466 -0.2007 0.026 Uiso 0.50 1 calc PR A -1
C41 C 1.0024(11) 1.0456(6) 0.0360(4) 0.0198(6) Uani 0.50 1 d PRDU A -1
N42 N 1.2149(11) 1.1421(6) 0.0436(4) 0.0200(7) Uani 0.50 1 d PRDU A -1
C43 C 1.1998(11) 1.2230(6) 0.1122(4) 0.0216(8) Uani 0.50 1 d PRDU A -1
H43 H 1.3399 1.2915 0.1201 0.026 Uiso 0.50 1 d PR A -1
C44 C 0.9975(18) 1.2148(9) 0.1703(6) 0.0223(10) Uani 0.50 1 d PDU A -1
H44 H 1.0092 1.2704 0.2198 0.027 Uiso 0.50 1 calc PR A -1
C45 C 0.7768(19) 1.1244(9) 0.1555(7) 0.0220(8) Uani 0.50 1 d PDU A -1
H45 H 0.6287 1.1204 0.1921 0.026 Uiso 0.50 1 calc PR A -1
C46 C 0.776(3) 1.0406(13) 0.0869(8) 0.0213(8) Uani 0.50 1 d PDU A -1
H46 H 0.6236 0.9797 0.0739 0.026 Uiso 0.50 1 calc PR A -1
C51 C 0.5823(12) 0.2926(5) 0.4481(3) 0.0298(12) Uani 1 1 d . . .
I1 I 0.54784(6) 0.39392(3) 0.331779(18) 0.0287(2) Uani 1 1 d . . .
F51A F 0.8306(9) 0.3200(4) 0.4820(3) 0.0600(13) Uani 1 1 d . . .
F51B F 0.4205(11) 0.3243(3) 0.5090(2) 0.0559(12) Uani 1 1 d . . .
C52 C 0.5136(10) 0.1514(5) 0.4294(3) 0.0204(10) Uani 1 1 d . . .
F52A F 0.6653(8) 0.1225(3) 0.3647(2) 0.0383(8) Uani 1 1 d . . .
F52B F 0.2610(6) 0.1259(3) 0.4007(2) 0.0370(8) Uani 1 1 d . . .
C53 C 0.5525(10) 0.0712(5) 0.5082(3) 0.0224(10) Uani 1 1 d . . .
F53A F 0.8140(6) 0.0860(3) 0.5268(2) 0.0292(7) Uani 1 1 d . . .
F53B F 0.4316(7) 0.1090(3) 0.5781(2) 0.0291(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
N11 C12 1.358(7) . ?
N11 C15 1.360(8) . ?
N11 H11 0.8800 . ?
C12 N13 1.314(7) . ?
C12 C21 1.460(7) . ?
N13 C14 1.371(9) . ?
N13 I1 2.856(5) . ?
C14 C15 1.355(9) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
C21 N22 1.353(7) . ?
C21 C26 1.401(7) . ?
N22 C23 1.344(7) . ?
C23 C24 1.380(8) . ?
C23 H23 0.9500 . ?
C24 C25 1.379(8) . ?
C24 H24 0.9500 . ?
C25 C26 1.362(9) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?
N31 C32 1.351(13) . ?
N31 C35 1.371(12) . ?
N31 H31 0.8800 . ?
C32 N33 1.289(11) . ?
C32 C41 1.471(8) . ?
N33 C34 1.369(12) . ?
C34 C35 1.325(12) . ?
C34 H34 0.9500 . ?
C35 H35 0.9500 . ?
C41 N42 1.3839 . ?
C41 C46 1.409(13) . ?
N42 C43 1.3649 . ?
C43 C44 1.374(10) . ?
C43 H43 0.9500 . ?
C44 C45 1.381(12) . ?
C44 H44 0.9500 . ?
C45 C46 1.371(14) . ?
C45 H45 0.9500 . ?
C46 H46 0.9500 . ?
C51 F51B 1.337(8) . ?
C51 F51A 1.347(7) . ?
C51 C52 1.550(7) . ?
C51 I1 2.154(5) . ?
C52 F52A 1.336(6) . ?
C52 F52B 1.340(6) . ?
C52 C53 1.549(7) . ?
C53 F53B 1.337(6) . ?
C53 F53A 1.348(6) . ?
C53 C53 1.577(10) 2_656 ?

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
C12 N11 C15 107.1(5) . . ?
C12 N11 H11 126.5 . . ?
C15 N11 H11 126.5 . . ?
N13 C12 N11 111.0(5) . . ?
N13 C12 C21 127.2(5) . . ?
N11 C12 C21 121.8(5) . . ?
C12 N13 C14 105.9(5) . . ?
C12 N13 I1 135.4(4) . . ?
C14 N13 I1 110.7(4) . . ?
C15 C14 N13 109.7(6) . . ?
C15 C14 H14 125.2 . . ?
N13 C14 H14 125.2 . . ?
C14 C15 N11 106.5(5) . . ?
C14 C15 H15 126.8 . . ?
N11 C15 H15 126.8 . . ?
N22 C21 C26 122.1(5) . . ?
N22 C21 C12 116.2(5) . . ?
C26 C21 C12 121.7(5) . . ?
C23 N22 C21 116.8(5) . . ?
N22 C23 C24 124.0(5) . . ?
N22 C23 H23 118.0 . . ?
C24 C23 H23 118.0 . . ?
C25 C24 C23 118.3(5) . . ?
C25 C24 H24 120.9 . . ?
C23 C24 H24 120.9 . . ?
C26 C25 C24 119.5(5) . . ?
C26 C25 H25 120.3 . . ?
C24 C25 H25 120.3 . . ?
C25 C26 C21 119.3(5) . . ?
C25 C26 H26 120.3 . . ?
C21 C26 H26 120.3 . . ?
C32 N31 C35 105.3(9) . . ?
C32 N31 H31 127.4 . . ?
C35 N31 H31 127.4 . . ?
N33 C32 N31 111.9(8) . . ?
N33 C32 C41 125.5(7) . . ?
N31 C32 C41 122.6(8) . . ?
C32 N33 C34 106.1(8) . . ?
C35 C34 N33 109.3(8) . . ?
C35 C34 H34 125.3 . . ?
N33 C34 H34 125.3 . . ?
C34 C35 N31 107.4(7) . . ?
C34 C35 H35 126.3 . . ?
N31 C35 H35 126.3 . . ?
N42 C41 C46 122.9(6) . . ?
N42 C41 C32 116.0(3) . . ?
C46 C41 C32 120.9(7) . . ?
C43 N42 C41 113.8 . . ?
N42 C43 C44 125.6(4) . . ?
N42 C43 H43 117.2 . . ?
C44 C43 H43 117.2 . . ?
C43 C44 C45 118.9(8) . . ?
C43 C44 H44 120.5 . . ?
C45 C44 H44 120.5 . . ?
C46 C45 C44 118.7(10) . . ?
C46 C45 H45 120.7 . . ?
C44 C45 H45 120.7 . . ?
C45 C46 C41 119.4(10) . . ?
C45 C46 H46 120.3 . . ?
C41 C46 H46 120.3 . . ?
F51B C51 F51A 107.5(5) . . ?
F51B C51 C52 108.6(4) . . ?
F51A C51 C52 108.4(5) . . ?
F51B C51 I1 110.0(4) . . ?
F51A C51 I1 110.2(4) . . ?
C52 C51 I1 112.0(3) . . ?
C51 I1 N13 176.0(2) . . ?
F52A C52 F52B 108.1(4) . . ?
F52A C52 C53 108.5(4) . . ?
F52B C52 C53 109.7(4) . . ?
F52A C52 C51 107.8(4) . . ?
F52B C52 C51 107.1(4) . . ?
C53 C52 C51 115.5(4) . . ?
F53B C53 F53A 108.9(4) . . ?
F53B C53 C52 110.0(4) . . ?
F53A C53 C52 107.7(4) . . ?
F53B C53 C53 107.8(5) . 2_656 ?
F53A C53 C53 107.5(5) . 2_656 ?
C52 C53 C53 114.8(5) . 2_656 ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C15 N11 C12 N13 -0.5(7) . . . . ?
C15 N11 C12 C21 179.4(5) . . . . ?
N11 C12 N13 C14 0.5(7) . . . . ?
C21 C12 N13 C14 -179.4(6) . . . . ?
N11 C12 N13 I1 144.8(4) . . . . ?
C21 C12 N13 I1 -35.1(9) . . . . ?
C12 N13 C14 C15 -0.4(8) . . . . ?
I1 N13 C14 C15 -154.4(5) . . . . ?
N13 C14 C15 N11 0.1(9) . . . . ?
C12 N11 C15 C14 0.2(8) . . . . ?
N13 C12 C21 N22 171.7(5) . . . . ?
N11 C12 C21 N22 -8.2(7) . . . . ?
N13 C12 C21 C26 -8.8(8) . . . . ?
N11 C12 C21 C26 171.3(5) . . . . ?
C26 C21 N22 C23 -0.5(7) . . . . ?
C12 C21 N22 C23 179.0(4) . . . . ?
C21 N22 C23 C24 0.3(8) . . . . ?
N22 C23 C24 C25 0.3(8) . . . . ?
C23 C24 C25 C26 -0.6(8) . . . . ?
C24 C25 C26 C21 0.4(8) . . . . ?
N22 C21 C26 C25 0.2(8) . . . . ?
C12 C21 C26 C25 -179.3(5) . . . . ?
C35 N31 C32 N33 -3.2(13) . . . . ?
C35 N31 C32 C41 -179.5(7) . . . . ?
N31 C32 N33 C34 2.3(12) . . . . ?
C41 C32 N33 C34 178.6(8) . . . . ?
C32 N33 C34 C35 -0.6(11) . . . . ?
N33 C34 C35 N31 -1.4(12) . . . . ?
C32 N31 C35 C34 2.7(12) . . . . ?
N33 C32 C41 N42 174.5(8) . . . . ?
N31 C32 C41 N42 -9.7(11) . . . . ?
N33 C32 C41 C46 -11.3(13) . . . . ?
N31 C32 C41 C46 164.6(14) . . . . ?
C46 C41 N42 C43 8.1(7) . . . . ?
C32 C41 N42 C43 -177.8(4) . . . . ?
C41 N42 C43 C44 -0.3(6) . . . . ?
N42 C43 C44 C45 -6.0(12) . . . . ?
C43 C44 C45 C46 4.6(16) . . . . ?
C44 C45 C46 C41 2.6(18) . . . . ?
N42 C41 C46 C45 -9.5(15) . . . . ?
C32 C41 C46 C45 176.7(9) . . . . ?
F51B C51 C52 F52A 176.1(4) . . . . ?
F51A C51 C52 F52A -67.4(5) . . . . ?
I1 C51 C52 F52A 54.4(5) . . . . ?
F51B C51 C52 F52B 60.0(5) . . . . ?
F51A C51 C52 F52B 176.4(4) . . . . ?
I1 C51 C52 F52B -61.8(5) . . . . ?
F51B C51 C52 C53 -62.5(6) . . . . ?
F51A C51 C52 C53 54.0(6) . . . . ?
I1 C51 C52 C53 175.8(3) . . . . ?
F52A C52 C53 F53B 171.8(4) . . . . ?
F52B C52 C53 F53B -70.4(5) . . . . ?
C51 C52 C53 F53B 50.7(6) . . . . ?
F52A C52 C53 F53A 53.3(5) . . . . ?
F52B C52 C53 F53A 171.1(4) . . . . ?
C51 C52 C53 F53A -67.8(6) . . . . ?
F52A C52 C53 C53 -66.5(7) . . . 2_656 ?
F52B C52 C53 C53 51.4(7) . . . 2_656 ?
C51 C52 C53 C53 172.4(5) . . . 2_656 ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N11 H11 N33 0.88 2.20 2.953(11) 142.9 .
N11 H11 N42 0.88 2.08 2.879(8) 150.0 2_775
N31 H31 N22 0.88 2.31 3.143(12) 158.4 2_775

_diffrn_measured_fraction_theta_max 0.916
_diffrn_reflns_theta_full        67.50
_diffrn_measured_fraction_theta_full 0.942
_refine_diff_density_max         0.769
_refine_diff_density_min         -0.997
_refine_diff_density_rms         0.161
_database_code_depnum_ccdc_archive 'CCDC 994321'
#######################################################################
#
#                 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_A3D8

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
TW-1-R38 2-(2-pyridyl)-imidazole, 1,4-diiodotetrafluorobenzene
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         
;
(C8 H7 N3) (C6 F4 I2)
;
_chemical_formula_sum            'C14 H7 F4 I2 N3'
_chemical_formula_weight         547.03

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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                   9.3920(5)
_cell_length_b                   10.5244(6)
_cell_length_c                   17.4011(10)
_cell_angle_alpha                106.841(2)
_cell_angle_beta                 92.190(2)
_cell_angle_gamma                106.005(2)
_cell_volume                     1569.34(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    9888
_cell_measurement_theta_min      2.44
_cell_measurement_theta_max      30.99

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.315
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1016
_exptl_absorpt_coefficient_mu    4.050
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4190
_exptl_absorpt_correction_T_max  0.7376
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      120(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            23253
_diffrn_reflns_av_R_equivalents  0.0245
_diffrn_reflns_av_sigmaI/netI    0.0303
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.09
_diffrn_reflns_theta_max         31.00
_reflns_number_total             9317
_reflns_number_gt                8146
_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)+(0.0300P)²+2.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         9317
_refine_ls_number_parameters     421
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0321
_refine_ls_R_factor_gt           0.0270
_refine_ls_wR_factor_ref         0.0688
_refine_ls_wR_factor_gt          0.0654
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_restrained_S_all      1.056
_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
N11 N 0.2055(3) 0.2586(3) 0.73188(14) 0.0173(4) Uani 1 1 d . . .
H11 H 0.174(4) 0.277(4) 0.774(2) 0.021 Uiso 1 1 d . . .
C12 C 0.2086(3) 0.3160(3) 0.67148(15) 0.0153(5) Uani 1 1 d . . .
N13 N 0.2949(3) 0.2722(2) 0.61776(13) 0.0174(4) Uani 1 1 d . . .
C14 C 0.3484(3) 0.1820(3) 0.64539(17) 0.0196(5) Uani 1 1 d . . .
H14A H 0.4131 0.1330 0.6191 0.024 Uiso 1 1 calc R . .
C15 C 0.2948(3) 0.1731(3) 0.71623(17) 0.0194(5) Uani 1 1 d . . .
H15A H 0.3153 0.1190 0.7480 0.023 Uiso 1 1 calc R . .
N21 N 0.0289(3) 0.4322(3) 0.72182(14) 0.0199(5) Uani 1 1 d . . .
C22 C 0.1271(3) 0.4147(3) 0.66800(15) 0.0150(5) Uani 1 1 d . . .
C23 C 0.1516(3) 0.4858(3) 0.61134(17) 0.0211(5) Uani 1 1 d . . .
H23A H 0.2216 0.4711 0.5743 0.025 Uiso 1 1 calc R . .
C24 C 0.0721(4) 0.5783(3) 0.60979(19) 0.0252(6) Uani 1 1 d . . .
H24A H 0.0861 0.6274 0.5713 0.030 Uiso 1 1 calc R . .
C25 C -0.0282(4) 0.5980(3) 0.6653(2) 0.0274(6) Uani 1 1 d . . .
H25A H -0.0836 0.6614 0.6660 0.033 Uiso 1 1 calc R . .
C26 C -0.0452(3) 0.5232(3) 0.71924(18) 0.0247(6) Uani 1 1 d . . .
H26A H -0.1140 0.5371 0.7571 0.030 Uiso 1 1 calc R . .
N31 N 0.8521(3) 0.3031(3) -0.16954(14) 0.0193(5) Uani 1 1 d . . .
H31 H 0.911(4) 0.330(4) -0.202(2) 0.023 Uiso 1 1 d . . .
C32 C 0.8843(3) 0.3010(3) -0.09325(15) 0.0157(5) Uani 1 1 d . . .
N33 N 0.7601(3) 0.2603(3) -0.06106(14) 0.0199(5) Uani 1 1 d . . .
C34 C 0.6456(3) 0.2351(3) -0.11997(18) 0.0245(6) Uani 1 1 d . . .
H34A H 0.5425 0.2040 -0.1146 0.029 Uiso 1 1 calc R . .
C35 C 0.6998(3) 0.2610(3) -0.18718(17) 0.0233(6) Uani 1 1 d . . .
H35A H 0.6437 0.2517 -0.2361 0.028 Uiso 1 1 calc R . .
N41 N 1.1447(3) 0.3399(3) -0.10275(14) 0.0182(4) Uani 1 1 d . . .
C42 C 1.0363(3) 0.3343(3) -0.05431(15) 0.0150(5) Uani 1 1 d . . .
C43 C 1.0650(3) 0.3568(3) 0.02833(16) 0.0189(5) Uani 1 1 d . . .
H43A H 0.9866 0.3545 0.0613 0.023 Uiso 1 1 calc R . .
C44 C 1.2106(3) 0.3824(3) 0.06155(16) 0.0200(5) Uani 1 1 d . . .
H44A H 1.2332 0.3962 0.1176 0.024 Uiso 1 1 calc R . .
C45 C 1.3222(3) 0.3877(3) 0.01227(18) 0.0219(5) Uani 1 1 d . . .
H45A H 1.4227 0.4047 0.0335 0.026 Uiso 1 1 calc R . .
C46 C 1.2839(3) 0.3677(3) -0.06906(17) 0.0210(5) Uani 1 1 d . . .
H46A H 1.3614 0.3742 -0.1026 0.025 Uiso 1 1 calc R . .
C51 C 0.4601(3) 0.2799(3) 0.35232(15) 0.0173(5) Uani 1 1 d . . .
I1 I 0.382969(18) 0.284633(18) 0.464671(10) 0.01703(4) Uani 1 1 d . . .
C52 C 0.5233(3) 0.1781(3) 0.31380(17) 0.0209(5) Uani 1 1 d . . .
F52 F 0.5290(2) 0.0770(2) 0.34585(11) 0.0299(4) Uani 1 1 d . . .
C53 C 0.5799(3) 0.1757(3) 0.24161(17) 0.0220(6) Uani 1 1 d . . .
F53 F 0.6415(2) 0.0749(2) 0.20863(11) 0.0327(4) Uani 1 1 d . . .
C54 C 0.5753(3) 0.2736(3) 0.20388(15) 0.0179(5) Uani 1 1 d . . .
I2 I 0.662501(19) 0.267682(19) 0.094363(10) 0.01841(5) Uani 1 1 d . . .
C55 C 0.5090(3) 0.3734(3) 0.24163(16) 0.0177(5) Uani 1 1 d . . .
F55 F 0.4975(2) 0.47130(18) 0.20796(10) 0.0226(3) Uani 1 1 d . . .
C56 C 0.4534(3) 0.3773(3) 0.31462(16) 0.0169(5) Uani 1 1 d . . .
F56 F 0.38964(19) 0.47664(18) 0.34742(10) 0.0225(3) Uani 1 1 d . . .
C61 C 0.9010(3) 0.0809(3) 0.51567(16) 0.0192(5) Uani 1 1 d . . .
I3 I 0.74557(2) 0.18989(2) 0.536688(12) 0.02488(5) Uani 1 1 d . . .
C62 C 0.9373(3) 0.0188(3) 0.57050(16) 0.0183(5) Uani 1 1 d . . .
F62 F 0.87769(19) 0.03515(18) 0.64040(10) 0.0228(3) Uani 1 1 d . . .
C66 C 0.9663(3) 0.0613(3) 0.44495(16) 0.0183(5) Uani 1 1 d . . .
F66 F 0.9384(2) 0.12094(19) 0.38990(10) 0.0246(4) Uani 1 1 d . . .
C71 C 0.9574(3) -0.0214(3) 0.91819(16) 0.0217(5) Uani 1 1 d . . .
I4 I 0.89703(4) -0.04981(2) 0.797548(12) 0.04370(7) Uani 1 1 d . . .
C72 C 0.8523(3) -0.0390(3) 0.97001(18) 0.0210(5) Uani 1 1 d . . .
F72 F 0.7068(2) -0.0799(2) 0.94199(14) 0.0394(5) Uani 1 1 d . . .
C76 C 1.1065(3) 0.0198(3) 0.94979(17) 0.0210(5) Uani 1 1 d . . .
F76 F 1.2141(2) 0.0428(2) 0.90254(13) 0.0376(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
N11 C12 1.353(3) . ?
N11 C15 1.371(4) . ?
N11 H11 0.79(4) . ?
C12 N13 1.325(3) . ?
C12 C22 1.463(4) . ?
N13 C14 1.376(4) . ?
N13 I1 2.848(2) . ?
C14 C15 1.367(4) . ?
C14 H14A 0.9500 . ?
C15 H15A 0.9500 . ?
N21 C26 1.339(4) . ?
N21 C22 1.349(3) . ?
C22 C23 1.391(4) . ?
C23 C24 1.386(4) . ?
C23 H23A 0.9500 . ?
C24 C25 1.387(4) . ?
C24 H24A 0.9500 . ?
C25 C26 1.378(4) . ?
C25 H25A 0.9500 . ?
C26 H26A 0.9500 . ?
N31 C32 1.358(3) . ?
N31 C35 1.369(4) . ?
N31 H31 0.86(4) . ?
C32 N33 1.331(3) . ?
C32 C42 1.461(4) . ?
N33 C34 1.371(4) . ?
N33 I2 2.875(2) . ?
C34 C35 1.362(4) . ?
C34 H34A 0.9500 . ?
C35 H35A 0.9500 . ?
N41 C46 1.330(4) . ?
N41 C42 1.346(3) . ?
C42 C43 1.391(4) . ?
C43 C44 1.386(4) . ?
C43 H43A 0.9500 . ?
C44 C45 1.379(4) . ?
C44 H44A 0.9500 . ?
C45 C46 1.387(4) . ?
C45 H45A 0.9500 . ?
C46 H46A 0.9500 . ?
C51 C56 1.381(4) . ?
C51 C52 1.384(4) . ?
C51 I1 2.103(3) . ?
C52 F52 1.349(3) . ?
C52 C53 1.379(4) . ?
C53 F53 1.342(3) . ?
C53 C54 1.381(4) . ?
C54 C55 1.384(4) . ?
C54 I2 2.094(3) . ?
C55 F55 1.350(3) . ?
C55 C56 1.386(4) . ?
C56 F56 1.342(3) . ?
C61 C62 1.382(4) . ?
C61 C66 1.383(4) . ?
C61 I3 2.075(3) . ?
I3 F66 3.2146(18) . ?
C62 F62 1.344(3) . ?
C62 C66 1.383(4) 2_756 ?
F62 I4 3.1271(17) . ?
C66 F66 1.342(3) . ?
C66 C62 1.383(4) 2_756 ?
C71 C72 1.373(4) . ?
C71 C76 1.386(4) . ?
C71 I4 2.066(3) . ?
C72 F72 1.340(3) . ?
C72 C76 1.375(4) 2_757 ?
C76 F76 1.342(3) . ?
C76 C72 1.375(4) 2_757 ?

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
C12 N11 C15 107.5(2) . . ?
C12 N11 H11 130(3) . . ?
C15 N11 H11 121(3) . . ?
N13 C12 N11 111.4(2) . . ?
N13 C12 C22 125.4(2) . . ?
N11 C12 C22 123.2(2) . . ?
C12 N13 C14 105.3(2) . . ?
C12 N13 I1 141.85(18) . . ?
C14 N13 I1 112.60(16) . . ?
C15 C14 N13 110.1(2) . . ?
C15 C14 H14A 124.9 . . ?
N13 C14 H14A 124.9 . . ?
C14 C15 N11 105.7(2) . . ?
C14 C15 H15A 127.1 . . ?
N11 C15 H15A 127.1 . . ?
C26 N21 C22 117.0(2) . . ?
N21 C22 C23 122.6(2) . . ?
N21 C22 C12 116.8(2) . . ?
C23 C22 C12 120.5(2) . . ?
C24 C23 C22 118.9(3) . . ?
C24 C23 H23A 120.5 . . ?
C22 C23 H23A 120.5 . . ?
C23 C24 C25 118.9(3) . . ?
C23 C24 H24A 120.5 . . ?
C25 C24 H24A 120.5 . . ?
C26 C25 C24 118.2(3) . . ?
C26 C25 H25A 120.9 . . ?
C24 C25 H25A 120.9 . . ?
N21 C26 C25 124.3(3) . . ?
N21 C26 H26A 117.9 . . ?
C25 C26 H26A 117.9 . . ?
C32 N31 C35 107.4(2) . . ?
C32 N31 H31 130(2) . . ?
C35 N31 H31 123(2) . . ?
N33 C32 N31 111.1(2) . . ?
N33 C32 C42 125.5(2) . . ?
N31 C32 C42 123.4(2) . . ?
C32 N33 C34 105.1(2) . . ?
C32 N33 I2 139.99(18) . . ?
C34 N33 I2 113.08(17) . . ?
C35 C34 N33 110.7(2) . . ?
C35 C34 H34A 124.7 . . ?
N33 C34 H34A 124.7 . . ?
C34 C35 N31 105.7(2) . . ?
C34 C35 H35A 127.1 . . ?
N31 C35 H35A 127.1 . . ?
C46 N41 C42 117.7(2) . . ?
N41 C42 C43 122.6(2) . . ?
N41 C42 C32 116.4(2) . . ?
C43 C42 C32 121.0(2) . . ?
C44 C43 C42 118.5(2) . . ?
C44 C43 H43A 120.7 . . ?
C42 C43 H43A 120.7 . . ?
C45 C44 C43 119.2(2) . . ?
C45 C44 H44A 120.4 . . ?
C43 C44 H44A 120.4 . . ?
C44 C45 C46 118.3(3) . . ?
C44 C45 H45A 120.8 . . ?
C46 C45 H45A 120.8 . . ?
N41 C46 C45 123.6(3) . . ?
N41 C46 H46A 118.2 . . ?
C45 C46 H46A 118.2 . . ?
C56 C51 C52 117.2(2) . . ?
C56 C51 I1 122.63(19) . . ?
C52 C51 I1 120.2(2) . . ?
C51 I1 N13 174.26(9) . . ?
F52 C52 C53 118.2(2) . . ?
F52 C52 C51 120.4(2) . . ?
C53 C52 C51 121.4(3) . . ?
F53 C53 C52 117.8(3) . . ?
F53 C53 C54 120.3(2) . . ?
C52 C53 C54 121.9(3) . . ?
C53 C54 C55 116.6(2) . . ?
C53 C54 I2 121.07(19) . . ?
C55 C54 I2 122.3(2) . . ?
C54 I2 N33 175.50(9) . . ?
F55 C55 C54 120.3(2) . . ?
F55 C55 C56 117.9(2) . . ?
C54 C55 C56 121.8(3) . . ?
F56 C56 C51 120.4(2) . . ?
F56 C56 C55 118.5(2) . . ?
C51 C56 C55 121.1(2) . . ?
C62 C61 C66 117.5(3) . . ?
C62 C61 I3 120.8(2) . . ?
C66 C61 I3 121.6(2) . . ?
C61 I3 F66 47.36(8) . . ?
F62 C62 C61 120.0(2) . . ?
F62 C62 C66 118.6(2) . 2_756 ?
C61 C62 C66 121.4(2) . 2_756 ?
C62 F62 I4 138.62(16) . . ?
F66 C66 C62 118.4(2) . 2_756 ?
F66 C66 C61 120.6(3) . . ?
C62 C66 C61 121.0(3) 2_756 . ?
C66 F66 I3 70.29(14) . . ?
C72 C71 C76 117.8(2) . . ?
C72 C71 I4 121.5(2) . . ?
C76 C71 I4 120.6(2) . . ?
C71 I4 F62 156.70(9) . . ?
F72 C72 C71 119.9(3) . . ?
F72 C72 C76 118.9(3) . 2_757 ?
C71 C72 C76 121.1(3) . 2_757 ?
F76 C76 C72 118.5(3) . 2_757 ?
F76 C76 C71 120.4(3) . . ?
C72 C76 C71 121.0(2) 2_757 . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C15 N11 C12 N13 0.1(3) . . . . ?
C15 N11 C12 C22 -179.4(2) . . . . ?
N11 C12 N13 C14 0.3(3) . . . . ?
C22 C12 N13 C14 179.7(3) . . . . ?
N11 C12 N13 I1 173.5(2) . . . . ?
C22 C12 N13 I1 -7.1(5) . . . . ?
C12 N13 C14 C15 -0.6(3) . . . . ?
I1 N13 C14 C15 -176.02(18) . . . . ?
N13 C14 C15 N11 0.6(3) . . . . ?
C12 N11 C15 C14 -0.4(3) . . . . ?
C26 N21 C22 C23 -0.5(4) . . . . ?
C26 N21 C22 C12 179.5(3) . . . . ?
N13 C12 C22 N21 171.1(3) . . . . ?
N11 C12 C22 N21 -9.5(4) . . . . ?
N13 C12 C22 C23 -8.9(4) . . . . ?
N11 C12 C22 C23 170.5(3) . . . . ?
N21 C22 C23 C24 -0.1(4) . . . . ?
C12 C22 C23 C24 179.9(3) . . . . ?
C22 C23 C24 C25 0.6(5) . . . . ?
C23 C24 C25 C26 -0.6(5) . . . . ?
C22 N21 C26 C25 0.5(5) . . . . ?
C24 C25 C26 N21 0.0(5) . . . . ?
C35 N31 C32 N33 -0.3(3) . . . . ?
C35 N31 C32 C42 177.5(3) . . . . ?
N31 C32 N33 C34 0.3(3) . . . . ?
C42 C32 N33 C34 -177.4(3) . . . . ?
N31 C32 N33 I2 -161.9(2) . . . . ?
C42 C32 N33 I2 20.4(5) . . . . ?
C32 N33 C34 C35 -0.3(4) . . . . ?
I2 N33 C34 C35 167.4(2) . . . . ?
N33 C34 C35 N31 0.1(4) . . . . ?
C32 N31 C35 C34 0.1(3) . . . . ?
C46 N41 C42 C43 0.2(4) . . . . ?
C46 N41 C42 C32 -178.9(2) . . . . ?
N33 C32 C42 N41 164.1(3) . . . . ?
N31 C32 C42 N41 -13.4(4) . . . . ?
N33 C32 C42 C43 -15.0(4) . . . . ?
N31 C32 C42 C43 167.6(3) . . . . ?
N41 C42 C43 C44 -1.6(4) . . . . ?
C32 C42 C43 C44 177.4(3) . . . . ?
C42 C43 C44 C45 1.3(4) . . . . ?
C43 C44 C45 C46 0.3(4) . . . . ?
C42 N41 C46 C45 1.6(4) . . . . ?
C44 C45 C46 N41 -1.9(5) . . . . ?
C56 C51 I1 N13 -164.3(8) . . . . ?
C52 C51 I1 N13 14.4(10) . . . . ?
C12 N13 I1 C51 -175.4(8) . . . . ?
C14 N13 I1 C51 -2.5(10) . . . . ?
C56 C51 C52 F52 -177.8(3) . . . . ?
I1 C51 C52 F52 3.4(4) . . . . ?
C56 C51 C52 C53 1.3(4) . . . . ?
I1 C51 C52 C53 -177.5(2) . . . . ?
F52 C52 C53 F53 -1.9(4) . . . . ?
C51 C52 C53 F53 179.0(3) . . . . ?
F52 C52 C53 C54 178.5(3) . . . . ?
C51 C52 C53 C54 -0.6(5) . . . . ?
F53 C53 C54 C55 179.6(3) . . . . ?
C52 C53 C54 C55 -0.9(4) . . . . ?
F53 C53 C54 I2 0.3(4) . . . . ?
C52 C53 C54 I2 179.9(2) . . . . ?
C53 C54 I2 N33 127.4(11) . . . . ?
C55 C54 I2 N33 -51.8(13) . . . . ?
C32 N33 I2 C54 149.1(11) . . . . ?
C34 N33 I2 C54 -12.2(13) . . . . ?
C53 C54 C55 F55 -178.8(2) . . . . ?
I2 C54 C55 F55 0.5(4) . . . . ?
C53 C54 C55 C56 1.6(4) . . . . ?
I2 C54 C55 C56 -179.1(2) . . . . ?
C52 C51 C56 F56 178.1(2) . . . . ?
I1 C51 C56 F56 -3.2(4) . . . . ?
C52 C51 C56 C55 -0.5(4) . . . . ?
I1 C51 C56 C55 178.2(2) . . . . ?
F55 C55 C56 F56 0.8(4) . . . . ?
C54 C55 C56 F56 -179.6(2) . . . . ?
F55 C55 C56 C51 179.5(2) . . . . ?
C54 C55 C56 C51 -0.9(4) . . . . ?
C62 C61 I3 F66 -178.9(3) . . . . ?
C66 C61 I3 F66 -2.29(18) . . . . ?
C66 C61 C62 F62 179.6(2) . . . . ?
I3 C61 C62 F62 -3.6(4) . . . . ?
C66 C61 C62 C66 -0.8(4) . . . 2_756 ?
I3 C61 C62 C66 176.0(2) . . . 2_756 ?
C61 C62 F62 I4 -177.40(17) . . . . ?
C66 C62 F62 I4 3.0(4) 2_756 . . . ?
C62 C61 C66 F66 -178.6(2) . . . . ?
I3 C61 C66 F66 4.7(4) . . . . ?
C62 C61 C66 C62 0.8(4) . . . 2_756 ?
I3 C61 C66 C62 -176.0(2) . . . 2_756 ?
C62 C66 F66 I3 177.9(3) 2_756 . . . ?
C61 C66 F66 I3 -2.7(2) . . . . ?
C61 I3 F66 C66 2.13(17) . . . . ?
C72 C71 I4 F62 116.0(3) . . . . ?
C76 C71 I4 F62 -62.3(4) . . . . ?
C62 F62 I4 C71 106.1(3) . . . . ?
C76 C71 C72 F72 -179.5(3) . . . . ?
I4 C71 C72 F72 2.2(4) . . . . ?
C76 C71 C72 C76 -1.6(5) . . . 2_757 ?
I4 C71 C72 C76 -179.9(2) . . . 2_757 ?
C72 C71 C76 F76 -178.0(3) . . . . ?
I4 C71 C76 F76 0.4(4) . . . . ?
C72 C71 C76 C72 1.6(5) . . . 2_757 ?
I4 C71 C76 C72 179.9(2) . . . 2_757 ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N11 H11 N41 0.79(4) 2.11(4) 2.882(3) 166(4) 1_456
N31 H31 N21 0.86(4) 2.10(4) 2.943(3) 166(3) 1_654

_diffrn_measured_fraction_theta_max 0.929
_diffrn_reflns_theta_full        30.00
_diffrn_measured_fraction_theta_full 0.953
_refine_diff_density_max         2.605
_refine_diff_density_min         -2.554
_refine_diff_density_rms         0.131
_database_code_depnum_ccdc_archive 'CCDC 994322'
#######################################################################
#
#                 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_A3D10

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
TW-1-68 [2-(2-pyridyl)-imidazole]2, 4,4'-diiodo-F8-biphenyl
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         
;
(C8 H7 N3)2 (C12 F8 I2)
;
_chemical_formula_sum            'C28 H14 F8 I2 N6'
_chemical_formula_weight         840.25

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                   24.4359(12)
_cell_length_b                   7.2667(4)
_cell_length_c                   16.3695(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 109.7130(10)
_cell_angle_gamma                90.00
_cell_volume                     2736.4(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    9901
_cell_measurement_theta_min      2.54
_cell_measurement_theta_max      33.09

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.040
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1608
_exptl_absorpt_coefficient_mu    2.386
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5157
_exptl_absorpt_correction_T_max  0.6734
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      120(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            14274
_diffrn_reflns_av_R_equivalents  0.0232
_diffrn_reflns_av_sigmaI/netI    0.0264
_diffrn_reflns_limit_h_min       -36
_diffrn_reflns_limit_h_max       37
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.64
_diffrn_reflns_theta_max         33.13
_reflns_number_total             4778
_reflns_number_gt                4451
_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)+(0.0300P)²+2.5000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4778
_refine_ls_number_parameters     202
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0251
_refine_ls_R_factor_gt           0.0231
_refine_ls_wR_factor_ref         0.0570
_refine_ls_wR_factor_gt          0.0559
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_restrained_S_all      1.029
_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
N11 N 0.45521(6) 0.2372(2) 0.33378(9) 0.0169(2) Uani 1 1 d . . .
H11 H 0.4856(11) 0.209(3) 0.3201(16) 0.020 Uiso 1 1 d . . .
C12 C 0.39892(7) 0.2208(2) 0.28117(10) 0.0156(3) Uani 1 1 d . . .
N13 N 0.36268(6) 0.2662(2) 0.32271(9) 0.0198(3) Uani 1 1 d . . .
C14 C 0.39749(7) 0.3135(2) 0.40504(11) 0.0212(3) Uani 1 1 d . . .
H14 H 0.3837 0.3532 0.4499 0.025 Uiso 1 1 calc R . .
C15 C 0.45469(7) 0.2956(2) 0.41323(11) 0.0200(3) Uani 1 1 d . . .
H15 H 0.4874 0.3189 0.4636 0.024 Uiso 1 1 calc R . .
N21 N 0.42487(6) 0.12922(19) 0.15818(8) 0.0176(2) Uani 1 1 d . . .
C22 C 0.38184(6) 0.1630(2) 0.19030(10) 0.0152(2) Uani 1 1 d . . .
C23 C 0.32333(7) 0.1448(2) 0.14105(10) 0.0191(3) Uani 1 1 d . . .
H23 H 0.2941 0.1728 0.1653 0.023 Uiso 1 1 calc R . .
C24 C 0.30842(7) 0.0849(2) 0.05589(11) 0.0212(3) Uani 1 1 d . . .
H24 H 0.2688 0.0695 0.0211 0.025 Uiso 1 1 calc R . .
C25 C 0.35225(7) 0.0480(2) 0.02242(10) 0.0203(3) Uani 1 1 d . . .
H25 H 0.3434 0.0062 -0.0356 0.024 Uiso 1 1 calc R . .
C26 C 0.40930(7) 0.0733(2) 0.07555(10) 0.0203(3) Uani 1 1 d . . .
H26 H 0.4392 0.0496 0.0520 0.024 Uiso 1 1 calc R . .
C31 C 0.15356(7) 0.1856(2) 0.29000(10) 0.0160(3) Uani 1 1 d . . .
I1 I 0.242147(4) 0.205435(13) 0.310276(6) 0.01785(4) Uani 1 1 d . . .
C32 C 0.11364(7) 0.2424(2) 0.21165(10) 0.0167(3) Uani 1 1 d . . .
F32 F 0.13176(5) 0.30702(15) 0.14851(7) 0.0247(2) Uani 1 1 d . . .
C33 C 0.05468(7) 0.2380(2) 0.19668(10) 0.0156(2) Uani 1 1 d . . .
F33 F 0.01930(5) 0.30698(13) 0.12116(7) 0.02093(19) Uani 1 1 d . . .
C34 C 0.03155(6) 0.1716(2) 0.25799(10) 0.0148(2) Uani 1 1 d . . .
C35 C 0.07209(6) 0.1101(2) 0.33568(9) 0.0146(2) Uani 1 1 d . . .
F35 F 0.05390(4) 0.03672(14) 0.39715(6) 0.01876(18) Uani 1 1 d . . .
C36 C 0.13122(6) 0.1209(2) 0.35178(9) 0.0154(2) Uani 1 1 d . . .
F36 F 0.16704(4) 0.06363(14) 0.42944(6) 0.02056(18) 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
N11 C12 1.3595(19) . ?
N11 C15 1.372(2) . ?
N11 H11 0.87(3) . ?
C12 N13 1.327(2) . ?
C12 C22 1.464(2) . ?
N13 C14 1.373(2) . ?
N13 I1 2.9167(14) . ?
C14 C15 1.365(2) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
N21 C26 1.339(2) . ?
N21 C22 1.3472(19) . ?
C22 C23 1.391(2) . ?
C23 C24 1.386(2) . ?
C23 H23 0.9500 . ?
C24 C25 1.384(2) . ?
C24 H24 0.9500 . ?
C25 C26 1.384(2) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?
C31 C36 1.383(2) . ?
C31 C32 1.387(2) . ?
C31 I1 2.0814(15) . ?
C32 F32 1.3391(17) . ?
C32 C33 1.378(2) . ?
C33 F33 1.3437(18) . ?
C33 C34 1.394(2) . ?
C34 C35 1.396(2) . ?
C34 C34 1.474(3) 2 ?
C35 F35 1.3400(16) . ?
C35 C36 1.381(2) . ?
C36 F36 1.3434(17) . ?

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
C12 N11 C15 107.26(13) . . ?
C12 N11 H11 125.8(16) . . ?
C15 N11 H11 126.8(16) . . ?
N13 C12 N11 111.16(14) . . ?
N13 C12 C22 125.51(14) . . ?
N11 C12 C22 123.32(14) . . ?
C12 N13 C14 105.41(14) . . ?
C12 N13 I1 139.40(11) . . ?
C14 N13 I1 112.52(10) . . ?
C15 C14 N13 110.33(15) . . ?
C15 C14 H14 124.8 . . ?
N13 C14 H14 124.8 . . ?
C14 C15 N11 105.84(15) . . ?
C14 C15 H15 127.1 . . ?
N11 C15 H15 127.1 . . ?
C26 N21 C22 117.15(13) . . ?
N21 C22 C23 122.78(14) . . ?
N21 C22 C12 117.14(13) . . ?
C23 C22 C12 120.09(14) . . ?
C24 C23 C22 118.87(14) . . ?
C24 C23 H23 120.6 . . ?
C22 C23 H23 120.6 . . ?
C25 C24 C23 118.88(14) . . ?
C25 C24 H24 120.6 . . ?
C23 C24 H24 120.6 . . ?
C24 C25 C26 118.37(15) . . ?
C24 C25 H25 120.8 . . ?
C26 C25 H25 120.8 . . ?
N21 C26 C25 123.92(14) . . ?
N21 C26 H26 118.0 . . ?
C25 C26 H26 118.0 . . ?
C36 C31 C32 116.70(14) . . ?
C36 C31 I1 123.55(11) . . ?
C32 C31 I1 119.74(11) . . ?
C31 I1 N13 173.26(5) . . ?
F32 C32 C33 117.97(14) . . ?
F32 C32 C31 120.38(14) . . ?
C33 C32 C31 121.64(14) . . ?
F33 C33 C32 117.67(13) . . ?
F33 C33 C34 120.03(13) . . ?
C32 C33 C34 122.25(14) . . ?
C33 C34 C35 115.56(13) . . ?
C33 C34 C34 121.73(16) . 2 ?
C35 C34 C34 122.68(16) . 2 ?
F35 C35 C36 118.03(13) . . ?
F35 C35 C34 119.89(13) . . ?
C36 C35 C34 122.08(13) . . ?
F36 C36 C35 117.96(13) . . ?
F36 C36 C31 120.34(13) . . ?
C35 C36 C31 121.69(14) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C15 N11 C12 N13 0.19(18) . . . . ?
C15 N11 C12 C22 179.34(14) . . . . ?
N11 C12 N13 C14 0.11(18) . . . . ?
C22 C12 N13 C14 -179.01(15) . . . . ?
N11 C12 N13 I1 -158.69(12) . . . . ?
C22 C12 N13 I1 22.2(3) . . . . ?
C12 N13 C14 C15 -0.37(19) . . . . ?
I1 N13 C14 C15 164.86(11) . . . . ?
N13 C14 C15 N11 0.49(19) . . . . ?
C12 N11 C15 C14 -0.41(18) . . . . ?
C26 N21 C22 C23 -1.0(2) . . . . ?
C26 N21 C22 C12 178.89(14) . . . . ?
N13 C12 C22 N21 177.43(15) . . . . ?
N11 C12 C22 N21 -1.6(2) . . . . ?
N13 C12 C22 C23 -2.6(2) . . . . ?
N11 C12 C22 C23 178.34(15) . . . . ?
N21 C22 C23 C24 1.7(2) . . . . ?
C12 C22 C23 C24 -178.24(15) . . . . ?
C22 C23 C24 C25 -0.9(2) . . . . ?
C23 C24 C25 C26 -0.3(2) . . . . ?
C22 N21 C26 C25 -0.3(2) . . . . ?
C24 C25 C26 N21 1.0(3) . . . . ?
C36 C31 C32 F32 179.94(14) . . . . ?
I1 C31 C32 F32 1.2(2) . . . . ?
C36 C31 C32 C33 1.2(2) . . . . ?
I1 C31 C32 C33 -177.58(12) . . . . ?
F32 C32 C33 F33 -3.1(2) . . . . ?
C31 C32 C33 F33 175.70(14) . . . . ?
F32 C32 C33 C34 179.33(14) . . . . ?
C31 C32 C33 C34 -1.9(2) . . . . ?
F33 C33 C34 C35 -177.41(13) . . . . ?
C32 C33 C34 C35 0.1(2) . . . . ?
F33 C33 C34 C34 1.01(19) . . . 2 ?
C32 C33 C34 C34 178.55(12) . . . 2 ?
C33 C34 C35 F35 -177.25(13) . . . . ?
C34 C34 C35 F35 4.35(18) 2 . . . ?
C33 C34 C35 C36 2.3(2) . . . . ?
C34 C34 C35 C36 -176.11(11) 2 . . . ?
F35 C35 C36 F36 -2.5(2) . . . . ?
C34 C35 C36 F36 177.96(13) . . . . ?
F35 C35 C36 C31 176.50(13) . . . . ?
C34 C35 C36 C31 -3.0(2) . . . . ?
C32 C31 C36 F36 -179.82(14) . . . . ?
I1 C31 C36 F36 -1.1(2) . . . . ?
C32 C31 C36 C35 1.2(2) . . . . ?
I1 C31 C36 C35 179.93(11) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N11 H11 N21 0.87(3) 2.17(3) 2.9934(19) 157(2) 2_655

_diffrn_measured_fraction_theta_max 0.915
_diffrn_reflns_theta_full        30.00
_diffrn_measured_fraction_theta_full 0.985
_refine_diff_density_max         1.073
_refine_diff_density_min         -0.856
_refine_diff_density_rms         0.107
_database_code_depnum_ccdc_archive 'CCDC 994323'
#######################################################################
#
#                 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_A4D2

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
TW-2-09 2-(2-pyrazinyl)-imidazole, I-(CF2)4-I
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         
;
(C7 H6 N4)2 (C4 F8 I2)
;
_chemical_formula_sum            'C18 H12 F8 I2 N8'
_chemical_formula_weight         746.16

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                   6.1488(7)
_cell_length_b                   6.3967(7)
_cell_length_c                   15.8942(19)
_cell_angle_alpha                81.861(4)
_cell_angle_beta                 85.950(4)
_cell_angle_gamma                72.388(3)
_cell_volume                     589.59(12)
_cell_formula_units_Z            1
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    2069
_cell_measurement_theta_min      2.59
_cell_measurement_theta_max      29.57

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.04
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.101
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             354
_exptl_absorpt_coefficient_mu    2.755
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5824
_exptl_absorpt_correction_T_max  0.8978
_exptl_absorpt_process_details   TWINABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      120(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            3658
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0347
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         1.29
_diffrn_reflns_theta_max         32.70
_reflns_number_total             3658
_reflns_number_gt                3313
_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)+(0.0750P)²+0.6000P] 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         3658
_refine_ls_number_parameters     265
_refine_ls_number_restraints     38
_refine_ls_R_factor_all          0.0490
_refine_ls_R_factor_gt           0.0314
_refine_ls_wR_factor_ref         0.1144
_refine_ls_wR_factor_gt          0.1023
_refine_ls_goodness_of_fit_ref   1.140
_refine_ls_restrained_S_all      1.135
_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
N11A N 0.5203(10) 0.8035(9) 0.3525(3) 0.0257(10) Uani 0.50 1 d PD A 1
C12A C 0.3769(9) 0.6942(9) 0.3875(4) 0.0188(9) Uani 0.50 1 d PD A 1
C13A C 0.3095(11) 0.5495(11) 0.3439(4) 0.0282(12) Uani 0.50 1 d PD A 1
H13A H 0.2051 0.4758 0.3706 0.034 Uiso 0.50 1 calc PR A 1
N14A N 0.3903(13) 0.5136(13) 0.2651(5) 0.0307(12) Uani 0.50 1 d PD A 1
C15A C 0.533(9) 0.623(8) 0.2292(9) 0.031(3) Uani 0.50 1 d PD A 1
H15A H 0.5917 0.6021 0.1731 0.037 Uiso 0.50 1 calc PR A 1
C16A C 0.5965(14) 0.7660(13) 0.2733(4) 0.0300(10) Uani 0.50 1 d PD A 1
H16A H 0.6988 0.8414 0.2460 0.036 Uiso 0.50 1 calc PR A 1
N21A N 0.3454(18) 0.8762(17) 0.5167(5) 0.0205(16) Uani 0.50 1 d PD A 1
H21A H 0.4425 0.9552 0.4989 0.025 Uiso 0.30(16) 1 d PR B 1
C22A C 0.2890(9) 0.7340(9) 0.4736(4) 0.0186(10) Uani 0.50 1 d PD A 1
N23A N 0.1393(11) 0.6453(11) 0.5166(5) 0.0217(12) Uani 0.50 1 d PD A 1
H23A H 0.0782 0.5471 0.5000 0.026 Uiso 0.20(16) 1 d PR B 1
C24A C 0.0969(10) 0.7342(10) 0.5922(4) 0.0231(11) Uani 0.50 1 d PD A 1
H24A H -0.0042 0.7019 0.6366 0.028 Uiso 0.50 1 calc PR A 1
C25A C 0.2244(11) 0.8775(10) 0.5932(4) 0.0239(11) Uani 0.50 1 d PD A 1
H25A H 0.2283 0.9609 0.6377 0.029 Uiso 0.50 1 calc PR A 1
N11B N 0.7568(9) 0.5705(9) 0.3557(3) 0.0242(10) Uani 0.50 1 d PD A 2
C12B C 0.6672(10) 0.4068(9) 0.3864(4) 0.0193(10) Uani 0.50 1 d PD A 2
C13B C 0.5245(11) 0.3417(11) 0.3377(4) 0.0270(12) Uani 0.50 1 d PD A 2
H13B H 0.4674 0.2227 0.3609 0.032 Uiso 0.50 1 calc PR A 2
N14B N 0.4669(13) 0.4405(13) 0.2605(5) 0.0307(12) Uani 0.50 1 d PD A 2
C15B C 0.550(9) 0.607(8) 0.2297(9) 0.031(3) Uani 0.50 1 d PD A 2
H15B H 0.5100 0.6834 0.1746 0.037 Uiso 0.50 1 calc PR A 2
C16B C 0.6955(13) 0.6695(13) 0.2774(4) 0.0300(10) Uani 0.50 1 d PD A 2
H16B H 0.7536 0.7873 0.2535 0.036 Uiso 0.50 1 calc PR A 2
N21B N 0.8786(11) 0.3459(12) 0.5189(5) 0.0216(12) Uani 0.50 1 d PD A 2
H21B H 0.9511 0.4491 0.5039 0.026 Uiso 0.22(16) 1 d PR C 2
C22B C 0.7287(9) 0.2970(9) 0.4719(4) 0.0178(9) Uani 0.50 1 d PD A 2
N23B N 0.6545(17) 0.1354(17) 0.5115(5) 0.0216(16) Uani 0.50 1 d PD A 2
H23B H 0.5556 0.0757 0.4922 0.026 Uiso 0.28(16) 1 d PR C 2
C24B C 0.7593(11) 0.0775(10) 0.5886(4) 0.0238(11) Uani 0.50 1 d PD A 2
H24B H 0.7387 -0.0348 0.6315 0.029 Uiso 0.50 1 calc PR A 2
C25B C 0.8979(11) 0.2067(10) 0.5938(4) 0.0240(11) Uani 0.50 1 d PD A 2
H25B H 0.9897 0.2011 0.6402 0.029 Uiso 0.50 1 calc PR A 2
I1 I 0.18662(3) 0.29213(3) 0.163206(12) 0.02828(9) Uani 1 1 d . . .
C31A C -0.0469(8) 0.1921(8) 0.0926(3) 0.0268(9) Uani 0.755(4) 1 d PD A 1
F31A F -0.1642(8) 0.0818(8) 0.1466(2) 0.0537(11) Uani 0.755(4) 1 d PD A 1
F31B F -0.2054(5) 0.3720(6) 0.0562(3) 0.0434(8) Uani 0.755(4) 1 d PD A 1
C32A C 0.0735(14) 0.0485(12) 0.0238(4) 0.0254(8) Uani 0.755(4) 1 d PD . 1
F32A F 0.2343(10) -0.1261(11) 0.0608(4) 0.0523(18) Uani 0.755(4) 1 d PD A 1
F32B F 0.1788(9) 0.1672(8) -0.0326(3) 0.0354(10) Uani 0.755(4) 1 d PD A 1
C31B C 0.014(2) 0.109(2) 0.1132(9) 0.0268(9) Uani 0.245(4) 1 d PD A 2
F31C F 0.005(2) -0.069(2) 0.1659(7) 0.0537(11) Uani 0.245(4) 1 d PD A 2
F31D F -0.2062(17) 0.2372(19) 0.1021(8) 0.0434(8) Uani 0.245(4) 1 d PD A 2
C32B C 0.098(5) 0.032(4) 0.0257(13) 0.0254(8) Uani 0.245(4) 1 d PD . 2
F32C F 0.297(4) -0.124(4) 0.0389(16) 0.0523(18) Uani 0.245(4) 1 d PD A 2
F32D F 0.126(4) 0.213(3) -0.0219(11) 0.0354(10) Uani 0.245(4) 1 d PD A 2


_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
N11A C12A 1.330(7) . ?
N11A C16A 1.341(8) . ?
C12A C13A 1.401(8) . ?
C12A C22A 1.463(8) . ?
C13A N14A 1.340(9) . ?
C13A H13A 0.9500 . ?
N14A C15A 1.329(15) . ?
N14A I1 2.865(7) . ?
C15A C16A 1.386(17) . ?
C15A H15A 0.9500 . ?
C16A H16A 0.9500 . ?
N21A C22A 1.348(9) . ?
N21A C25A 1.379(9) . ?
N21A H21A 0.9000 . ?
C22A N23A 1.324(8) . ?
N23A H23A 0.9001 . ?
N23A C24A 1.376(9) . ?
N23A H23A 0.9001 . ?
C24A C25A 1.377(7) . ?
C24A H24A 0.9500 . ?
C25A H25A 0.9500 . ?
N11B C16B 1.337(8) . ?
N11B C12B 1.344(7) . ?
C12B C13B 1.397(8) . ?
C12B C22B 1.457(7) . ?
C13B N14B 1.319(9) . ?
C13B H13B 0.9500 . ?
N14B C15B 1.336(15) . ?
N14B I1 2.836(7) . ?
C15B C16B 1.389(17) . ?
C15B H15B 0.9500 . ?
C16B H16B 0.9500 . ?
N21B C22B 1.358(8) . ?
N21B C25B 1.370(9) . ?
N21B H21B 0.9000 . ?
C22B N23B 1.317(10) . ?
N23B H23B 0.9000 . ?
N23B C24B 1.375(10) . ?
N23B H23B 0.9000 . ?
C24B C25B 1.368(8) . ?
C24B H24B 0.9500 . ?
C25B H25B 0.9500 . ?
I1 C31B 2.063(14) . ?
I1 C31A 2.172(5) . ?
C31A F31A 1.342(5) . ?
C31A F31B 1.350(6) . ?
C31A C32A 1.532(7) . ?
C32A F32A 1.341(6) . ?
C32A F32B 1.350(6) . ?
C32A C32A 1.53(2) 2 ?
C31B F31C 1.328(14) . ?
C31B F31D 1.363(14) . ?
C31B C32B 1.544(16) . ?
C32B F32C 1.331(17) . ?
C32B F32D 1.342(16) . ?
C32B C32B 1.67(7) 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
C12A N11A C16A 115.9(6) . . ?
N11A C12A C13A 121.9(6) . . ?
N11A C12A C22A 117.0(5) . . ?
C13A C12A C22A 121.1(5) . . ?
N14A C13A C12A 120.9(6) . . ?
N14A C13A H13A 119.5 . . ?
C12A C13A H13A 119.5 . . ?
C15A N14A C13A 117.8(12) . . ?
C15A N14A I1 119.9(7) . . ?
C13A N14A I1 120.8(5) . . ?
N14A C15A C16A 120(2) . . ?
N14A C15A H15A 119.8 . . ?
C16A C15A H15A 119.8 . . ?
N11A C16A C15A 123.1(11) . . ?
N11A C16A H16A 118.4 . . ?
C15A C16A H16A 118.4 . . ?
C22A N21A C25A 106.6(7) . . ?
C22A N21A H21A 126.7 . . ?
C25A N21A H21A 126.8 . . ?
N23A C22A N21A 112.2(6) . . ?
N23A C22A C12A 125.0(5) . . ?
N21A C22A C12A 122.8(6) . . ?
H23A N23A C22A 127.2 . . ?
H23A N23A C24A 127.1 . . ?
C22A N23A C24A 105.7(5) . . ?
C22A N23A H23A 127.2 . . ?
C24A N23A H23A 127.1 . . ?
N23A C24A C25A 109.2(5) . . ?
N23A C24A H24A 125.4 . . ?
C25A C24A H24A 125.4 . . ?
C24A C25A N21A 106.4(6) . . ?
C24A C25A H25A 126.8 . . ?
N21A C25A H25A 126.8 . . ?
C16B N11B C12B 115.9(5) . . ?
N11B C12B C13B 121.3(5) . . ?
N11B C12B C22B 117.3(5) . . ?
C13B C12B C22B 121.4(5) . . ?
N14B C13B C12B 121.9(6) . . ?
N14B C13B H13B 119.1 . . ?
C12B C13B H13B 119.1 . . ?
C13B N14B C15B 117.6(12) . . ?
C13B N14B I1 120.4(5) . . ?
C15B N14B I1 122.0(10) . . ?
N14B C15B C16B 121(2) . . ?
N14B C15B H15B 119.7 . . ?
C16B C15B H15B 119.7 . . ?
N11B C16B C15B 122.6(11) . . ?
N11B C16B H16B 118.7 . . ?
C15B C16B H16B 118.7 . . ?
C22B N21B C25B 106.4(6) . . ?
C22B N21B H21B 126.9 . . ?
C25B N21B H21B 126.7 . . ?
N23B C22B N21B 112.0(6) . . ?
N23B C22B C12B 125.0(6) . . ?
N21B C22B C12B 123.0(5) . . ?
H23B N23B C22B 127.2 . . ?
H23B N23B C24B 127.2 . . ?
C22B N23B C24B 105.6(7) . . ?
C22B N23B H23B 127.2 . . ?
C24B N23B H23B 127.2 . . ?
C25B C24B N23B 109.4(6) . . ?
C25B C24B H24B 125.3 . . ?
N23B C24B H24B 125.3 . . ?
C24B C25B N21B 106.6(6) . . ?
C24B C25B H25B 126.7 . . ?
N21B C25B H25B 126.7 . . ?
C31B I1 N14B 165.2(4) . . ?
C31A I1 N14B 176.3(2) . . ?
C31B I1 N14A 168.4(4) . . ?
C31A I1 N14A 165.2(2) . . ?
F31A C31A F31B 105.4(4) . . ?
F31A C31A C32A 109.4(5) . . ?
F31B C31A C32A 109.0(4) . . ?
F31A C31A I1 109.6(3) . . ?
F31B C31A I1 110.1(3) . . ?
C32A C31A I1 113.1(5) . . ?
F32A C32A F32B 107.9(7) . . ?
F32A C32A C31A 108.2(6) . . ?
F32B C32A C31A 108.5(6) . . ?
F32A C32A C32A 105.5(8) . 2 ?
F32B C32A C32A 109.4(7) . 2 ?
C31A C32A C32A 117.0(7) . 2 ?
F31C C31B F31D 106.1(12) . . ?
F31C C31B C32B 106.8(12) . . ?
F31D C31B C32B 105.1(14) . . ?
F31C C31B I1 112.3(10) . . ?
F31D C31B I1 107.9(9) . . ?
C32B C31B I1 117.7(14) . . ?
F32C C32B F32D 111(2) . . ?
F32C C32B C31B 105.9(18) . . ?
F32D C32B C31B 104.0(16) . . ?
F32C C32B C32B 117(2) . 2 ?
F32D C32B C32B 104(2) . 2 ?
C31B C32B C32B 114(2) . 2 ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C16A N11A C12A C13A -0.2(9) . . . . ?
C16A N11A C12A C22A -179.3(6) . . . . ?
N11A C12A C13A N14A 0.9(10) . . . . ?
C22A C12A C13A N14A 180.0(6) . . . . ?
C12A C13A N14A C15A -1(3) . . . . ?
C12A C13A N14A I1 -167.2(5) . . . . ?
C13A N14A C15A C16A 1(5) . . . . ?
I1 N14A C15A C16A 167(3) . . . . ?
C12A N11A C16A C15A 0(3) . . . . ?
N14A C15A C16A N11A 0(6) . . . . ?
C25A N21A C22A N23A 0.5(10) . . . . ?
C25A N21A C22A C12A 177.6(6) . . . . ?
N11A C12A C22A N23A 177.6(6) . . . . ?
C13A C12A C22A N23A -1.5(9) . . . . ?
N11A C12A C22A N21A 0.8(9) . . . . ?
C13A C12A C22A N21A -178.3(7) . . . . ?
N21A C22A N23A H23A 179.8 . . . . ?
C12A C22A N23A H23A 2.8 . . . . ?
N21A C22A N23A C24A -0.3(9) . . . . ?
C12A C22A N23A C24A -177.3(5) . . . . ?
H23A N23A C24A C25A 179.9 . . . . ?
C22A N23A C24A C25A 0.0(7) . . . . ?
N23A C24A C25A N21A 0.3(8) . . . . ?
C22A N21A C25A C24A -0.4(9) . . . . ?
C16B N11B C12B C13B 1.9(9) . . . . ?
C16B N11B C12B C22B -179.4(6) . . . . ?
N11B C12B C13B N14B -1.6(10) . . . . ?
C22B C12B C13B N14B 179.7(6) . . . . ?
C12B C13B N14B C15B 0(3) . . . . ?
C12B C13B N14B I1 178.3(5) . . . . ?
C13B N14B C15B C16B 1(5) . . . . ?
I1 N14B C15B C16B -177(3) . . . . ?
C12B N11B C16B C15B -1(3) . . . . ?
N14B C15B C16B N11B -1(6) . . . . ?
C25B N21B C22B N23B -0.7(9) . . . . ?
C25B N21B C22B C12B -178.4(6) . . . . ?
N11B C12B C22B N23B 179.4(7) . . . . ?
C13B C12B C22B N23B -1.9(10) . . . . ?
N11B C12B C22B N21B -3.2(9) . . . . ?
C13B C12B C22B N21B 175.5(6) . . . . ?
N21B C22B N23B H23B -179.5 . . . . ?
C12B C22B N23B H23B -1.9 . . . . ?
N21B C22B N23B C24B 0.6(10) . . . . ?
C12B C22B N23B C24B 178.3(6) . . . . ?
H23B N23B C24B C25B 179.8 . . . . ?
C22B N23B C24B C25B -0.3(10) . . . . ?
N23B C24B C25B N21B -0.1(9) . . . . ?
C22B N21B C25B C24B 0.4(8) . . . . ?
F31A C31A C32A F32A -66.9(8) . . . . ?
F31B C31A C32A F32A 178.3(6) . . . . ?
I1 C31A C32A F32A 55.5(7) . . . . ?
F31A C31A C32A F32B 176.3(6) . . . . ?
F31B C31A C32A F32B 61.5(7) . . . . ?
I1 C31A C32A F32B -61.3(6) . . . . ?
F31A C31A C32A C32A 52.0(9) . . . 2 ?
F31B C31A C32A C32A -62.8(8) . . . 2 ?
I1 C31A C32A C32A 174.4(6) . . . 2 ?
F31C C31B C32B F32C -57(2) . . . . ?
F31D C31B C32B F32C -169.0(19) . . . . ?
I1 C31B C32B F32C 71(2) . . . . ?
F31C C31B C32B F32D -173.9(18) . . . . ?
F31D C31B C32B F32D 74(2) . . . . ?
I1 C31B C32B F32D -46(2) . . . . ?
F31C C31B C32B C32B 74(2) . . . 2 ?
F31D C31B C32B C32B -39(2) . . . 2 ?
I1 C31B C32B C32B -158.9(17) . . . 2 ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N21A H21A N21A 0.90 1.91 2.802(18) 169.3 2_676
N23A H23A N23A 0.90 2.12 3.001(13) 164.5 2_566
N21B H21B N21B 0.90 1.90 2.793(14) 174.7 2_766
N23B H23B N23B 0.90 2.14 3.003(18) 159.9 2_656

_diffrn_measured_fraction_theta_max 0.842
_diffrn_reflns_theta_full        27.50
_diffrn_measured_fraction_theta_full 0.984
_refine_diff_density_max         2.122
_refine_diff_density_min         -0.925
_refine_diff_density_rms         0.191
_database_code_depnum_ccdc_archive 'CCDC 994324'
#######################################################################
#
#                 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_A4D8

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
TW-1-M1 2-(2-pyrazinyl)-imidazole, 1,4-diiodotetrafluorobenzene, I-(CF2)4-I
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         
;
(C7 H6 N4)2 (C6 F4 I2)
;
_chemical_formula_sum            'C20 H12 F4 I2 N8'
_chemical_formula_weight         694.18

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'
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   P2(1)/c

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

_cell_length_a                   11.0717(6)
_cell_length_b                   10.6250(6)
_cell_length_c                   10.1858(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 108.814(2)
_cell_angle_gamma                90.00
_cell_volume                     1134.20(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    7251
_cell_measurement_theta_min      2.85
_cell_measurement_theta_max      32.63

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.033
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             660
_exptl_absorpt_coefficient_mu    2.832
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4460
_exptl_absorpt_correction_T_max  0.7649
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      120(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            10920
_diffrn_reflns_av_R_equivalents  0.0248
_diffrn_reflns_av_sigmaI/netI    0.0283
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         1.94
_diffrn_reflns_theta_max         32.64
_reflns_number_total             3791
_reflns_number_gt                3467
_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)+(0.0300P)²+0.5000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3791
_refine_ls_number_parameters     157
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0249
_refine_ls_R_factor_gt           0.0219
_refine_ls_wR_factor_ref         0.0595
_refine_ls_wR_factor_gt          0.0580
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_restrained_S_all      1.077
_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
N11 N 0.23160(15) 0.24421(14) 0.04367(17) 0.0143(3) Uani 1 1 d . . .
H11 H 0.250(3) 0.259(2) -0.021(3) 0.017 Uiso 1 1 d . . .
C12 C 0.30215(17) 0.26306(16) 0.17827(17) 0.0128(3) Uani 1 1 d . . .
N13 N 0.23931(15) 0.22810(14) 0.26321(15) 0.0141(3) Uani 1 1 d . . .
C14 C 0.12359(17) 0.18580(17) 0.17802(19) 0.0156(3) Uani 1 1 d . . .
H14 H 0.0570 0.1547 0.2090 0.019 Uiso 1 1 calc R . .
C15 C 0.11773(17) 0.19479(17) 0.04242(18) 0.0157(3) Uani 1 1 d . . .
H15 H 0.0483 0.1713 -0.0367 0.019 Uiso 1 1 calc R . .
N21 N 0.46949(16) 0.36912(16) 0.12256(16) 0.0191(3) Uani 1 1 d . . .
C22 C 0.42842(17) 0.31957(16) 0.22133(18) 0.0136(3) Uani 1 1 d . . .
C23 C 0.50178(18) 0.32517(18) 0.36110(19) 0.0177(3) Uani 1 1 d . . .
H23 H 0.4700 0.2878 0.4281 0.021 Uiso 1 1 calc R . .
N24 N 0.61488(16) 0.38141(16) 0.40290(16) 0.0196(3) Uani 1 1 d . . .
C25 C 0.6562(2) 0.43195(18) 0.3048(2) 0.0217(4) Uani 1 1 d . . .
H25 H 0.7364 0.4735 0.3309 0.026 Uiso 1 1 calc R . .
C26 C 0.5838(2) 0.4246(2) 0.1656(2) 0.0239(4) Uani 1 1 d . . .
H26 H 0.6166 0.4604 0.0986 0.029 Uiso 1 1 calc R . .
C31 C 0.91005(17) 0.47200(16) 0.86900(17) 0.0150(3) Uani 1 1 d . . .
I1 I 0.778157(11) 0.426004(10) 0.675902(11) 0.01551(5) Uani 1 1 d . . .
C32 C 0.89181(19) 0.43341(16) 0.9913(2) 0.0158(3) Uani 1 1 d . . .
F32 F 0.78845(12) 0.36689(12) 0.98768(12) 0.0236(2) Uani 1 1 d . . .
C36 C 1.01990(18) 0.53964(17) 0.88116(18) 0.0157(3) Uani 1 1 d . . .
F36 F 1.04345(13) 0.58175(10) 0.76738(12) 0.0200(2) 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
N11 C12 1.356(2) . ?
N11 C15 1.362(2) . ?
N11 H11 0.76(3) . ?
C12 N13 1.326(2) . ?
C12 C22 1.453(2) . ?
N13 C14 1.371(2) . ?
C14 C15 1.365(2) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
N21 C26 1.335(3) . ?
N21 C22 1.338(2) . ?
C22 C23 1.394(2) . ?
C23 N24 1.328(2) . ?
C23 H23 0.9500 . ?
N24 C25 1.338(3) . ?
N24 I1 2.8254(16) . ?
C25 C26 1.388(3) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?
C31 C36 1.383(3) . ?
C31 C32 1.387(3) . ?
C31 I1 2.0945(17) . ?
C32 F32 1.335(2) . ?
C32 C36 1.381(3) 3_767 ?
C36 F36 1.344(2) . ?
C36 C32 1.381(3) 3_767 ?

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
C12 N11 C15 107.22(15) . . ?
C12 N11 H11 128(2) . . ?
C15 N11 H11 125(2) . . ?
N13 C12 N11 111.46(16) . . ?
N13 C12 C22 125.08(15) . . ?
N11 C12 C22 123.41(15) . . ?
C12 N13 C14 104.99(14) . . ?
C15 C14 N13 110.32(16) . . ?
C15 C14 H14 124.8 . . ?
N13 C14 H14 124.8 . . ?
N11 C15 C14 106.01(16) . . ?
N11 C15 H15 127.0 . . ?
C14 C15 H15 127.0 . . ?
C26 N21 C22 116.27(17) . . ?
N21 C22 C23 121.56(16) . . ?
N21 C22 C12 117.56(15) . . ?
C23 C22 C12 120.85(16) . . ?
N24 C23 C22 121.69(17) . . ?
N24 C23 H23 119.2 . . ?
C22 C23 H23 119.2 . . ?
C23 N24 C25 117.09(17) . . ?
C23 N24 I1 128.98(12) . . ?
C25 N24 I1 113.78(13) . . ?
N24 C25 C26 121.09(19) . . ?
N24 C25 H25 119.5 . . ?
C26 C25 H25 119.5 . . ?
N21 C26 C25 122.29(19) . . ?
N21 C26 H26 118.9 . . ?
C25 C26 H26 118.9 . . ?
C36 C31 C32 116.85(16) . . ?
C36 C31 I1 122.13(13) . . ?
C32 C31 I1 121.01(14) . . ?
C31 I1 N24 173.90(6) . . ?
F32 C32 C36 118.42(17) . 3_767 ?
F32 C32 C31 120.24(16) . . ?
C36 C32 C31 121.33(17) 3_767 . ?
F36 C36 C32 117.85(17) . 3_767 ?
F36 C36 C31 120.34(16) . . ?
C32 C36 C31 121.81(16) 3_767 . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C15 N11 C12 N13 0.1(2) . . . . ?
C15 N11 C12 C22 -177.51(16) . . . . ?
N11 C12 N13 C14 -0.3(2) . . . . ?
C22 C12 N13 C14 177.26(16) . . . . ?
C12 N13 C14 C15 0.4(2) . . . . ?
C12 N11 C15 C14 0.17(19) . . . . ?
N13 C14 C15 N11 -0.3(2) . . . . ?
C26 N21 C22 C23 -0.4(3) . . . . ?
C26 N21 C22 C12 177.53(17) . . . . ?
N13 C12 C22 N21 -168.77(17) . . . . ?
N11 C12 C22 N21 8.5(3) . . . . ?
N13 C12 C22 C23 9.2(3) . . . . ?
N11 C12 C22 C23 -173.53(17) . . . . ?
N21 C22 C23 N24 1.0(3) . . . . ?
C12 C22 C23 N24 -176.94(17) . . . . ?
C22 C23 N24 C25 -0.5(3) . . . . ?
C22 C23 N24 I1 174.80(13) . . . . ?
C23 N24 C25 C26 -0.5(3) . . . . ?
I1 N24 C25 C26 -176.45(16) . . . . ?
C22 N21 C26 C25 -0.5(3) . . . . ?
N24 C25 C26 N21 1.0(3) . . . . ?
C36 C31 C32 F32 -179.48(16) . . . . ?
I1 C31 C32 F32 -0.7(2) . . . . ?
C36 C31 C32 C36 -0.6(3) . . . 3_767 ?
I1 C31 C32 C36 178.17(14) . . . 3_767 ?
C32 C31 C36 F36 -179.11(16) . . . . ?
I1 C31 C36 F36 2.1(2) . . . . ?
C32 C31 C36 C32 0.6(3) . . . 3_767 ?
I1 C31 C36 C32 -178.15(14) . . . 3_767 ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N11 H11 N13 0.76(3) 2.17(3) 2.900(2) 161(3) 4_565

_diffrn_measured_fraction_theta_max 0.913
_diffrn_reflns_theta_full        30.00
_diffrn_measured_fraction_theta_full 0.983
_refine_diff_density_max         0.620
_refine_diff_density_min         -0.677
_refine_diff_density_rms         0.159
_database_code_depnum_ccdc_archive 'CCDC 994325'
#######################################################################
#
#                 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_A4D9

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
TW-1-59 [2-(2-pyrazinyl)-imidazole]2, 1,3,5-F3-2,4,6-I3-benzene
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         
;
(C7 H6 N4)2 (C6 F3 I3)
;
_chemical_formula_sum            'C20 H12 F3 I3 N8'
_chemical_formula_weight         802.08

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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           Orthorhombic
_symmetry_space_group_name_H-M   Pbcn

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

_cell_length_a                   33.0655(16)
_cell_length_b                   9.8284(5)
_cell_length_c                   7.3176(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2378.08(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    9054
_cell_measurement_theta_min      2.46
_cell_measurement_theta_max      32.44

_exptl_crystal_description       rod
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.04
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.240
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1496
_exptl_absorpt_coefficient_mu    3.993
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4010
_exptl_absorpt_correction_T_max  0.8566
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      120(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            36207
_diffrn_reflns_av_R_equivalents  0.0298
_diffrn_reflns_av_sigmaI/netI    0.0178
_diffrn_reflns_limit_h_min       -49
_diffrn_reflns_limit_h_max       46
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.16
_diffrn_reflns_theta_max         32.52
_reflns_number_total             4246
_reflns_number_gt                3689
_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)+(0.0200P)²+2.0000P] 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         4246
_refine_ls_number_parameters     157
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0269
_refine_ls_R_factor_gt           0.0212
_refine_ls_wR_factor_ref         0.0480
_refine_ls_wR_factor_gt          0.0460
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_restrained_S_all      1.046
_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
N11A N 0.75884(4) -0.11260(13) 0.2832(2) 0.0159(3) Uani 0.80(3) 1 d P A 1
H11 H 0.7502 -0.1970 0.2927 0.019 Uiso 0.80(3) 1 calc PR A 1
N11B N 0.75884(4) -0.11260(13) 0.2832(2) 0.0159(3) Uani 0.20(3) 1 d P A 2
C12 C 0.73849(5) 0.00044(15) 0.3322(2) 0.0142(3) Uani 1 1 d . . .
N13A N 0.76000(4) 0.11177(13) 0.2995(2) 0.0160(3) Uani 0.80(3) 1 d P A 1
N13B N 0.76000(4) 0.11177(13) 0.2995(2) 0.0160(3) Uani 0.20(3) 1 d P A 2
H13 H 0.7528 0.1966 0.3197 0.019 Uiso 0.20(3) 1 calc PR A 2
C14 C 0.79559(5) 0.06687(17) 0.2281(2) 0.0181(3) Uani 1 1 d . . .
H14 H 0.8174 0.1236 0.1918 0.022 Uiso 1 1 calc R A 1
C15 C 0.79532(5) -0.07188(17) 0.2163(2) 0.0183(3) Uani 1 1 d . A .
H15 H 0.8163 -0.1285 0.1706 0.022 Uiso 1 1 calc R B 1
N21 N 0.67968(5) -0.12185(15) 0.4304(2) 0.0196(3) Uani 1 1 d . . .
C22 C 0.69786(5) -0.00119(16) 0.4092(2) 0.0149(3) Uani 1 1 d . A .
C23 C 0.67856(5) 0.11993(17) 0.4570(2) 0.0184(3) Uani 1 1 d . . .
H23 H 0.6928 0.2033 0.4439 0.022 Uiso 1 1 calc R A .
N24 N 0.64105(5) 0.12230(16) 0.5200(2) 0.0222(3) Uani 1 1 d . A .
C25 C 0.62257(6) 0.0019(2) 0.5383(3) 0.0240(4) Uani 1 1 d . . .
H25 H 0.5955 -0.0010 0.5817 0.029 Uiso 1 1 calc R A .
C26 C 0.64209(6) -0.11860(19) 0.4953(3) 0.0225(3) Uani 1 1 d . A .
H26 H 0.6281 -0.2021 0.5129 0.027 Uiso 1 1 calc R . .
C31 C 0.5000 0.6707(2) 0.7500 0.0192(5) Uani 1 2 d S . .
I31 I 0.5000 0.881980(18) 0.7500 0.03018(5) Uani 1 2 d S . .
C32 C 0.53344(5) 0.59792(18) 0.6921(2) 0.0187(3) Uani 1 1 d . . .
F32 F 0.56590(4) 0.66608(11) 0.63251(15) 0.0251(2) Uani 1 1 d . . .
C33 C 0.53476(5) 0.45699(18) 0.6936(2) 0.0179(3) Uani 1 1 d . A .
I33 I 0.585169(3) 0.343306(12) 0.616810(16) 0.02156(4) Uani 1 1 d . . .
C34 C 0.5000 0.3906(2) 0.7500 0.0177(4) Uani 1 2 d S . .
F34 F 0.5000 0.25441(15) 0.7500 0.0253(3) Uani 0.50 1 d P A .


_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
N11A C12 1.348(2) . ?
N11A C15 1.362(2) . ?
N11A H11 0.8800 . ?
C12 N13A 1.327(2) . ?
C12 C22 1.457(2) . ?
N13A C14 1.361(2) . ?
C14 C15 1.366(2) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
N21 C26 1.331(2) . ?
N21 C22 1.338(2) . ?
C22 C23 1.395(2) . ?
C23 N24 1.323(2) . ?
C23 H23 0.9500 . ?
N24 C25 1.339(2) . ?
N24 I33 2.9383(15) . ?
C25 C26 1.385(3) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?
C31 C32 1.383(2) 3_656 ?
C31 C32 1.383(2) . ?
C31 I31 2.077(2) . ?
C32 F32 1.338(2) . ?
C32 C33 1.386(2) . ?
C33 C34 1.385(2) . ?
C33 I33 2.0837(17) . ?
C34 F34 1.338(3) . ?
C34 C33 1.385(2) 3_656 ?

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
C12 N11A C15 107.20(13) . . ?
C12 N11A H11 126.4 . . ?
C15 N11A H11 126.4 . . ?
N13A C12 N11A 111.36(14) . . ?
N13A C12 C22 124.97(14) . . ?
N11A C12 C22 123.66(14) . . ?
C12 N13A C14 105.39(13) . . ?
N13A C14 C15 110.00(15) . . ?
N13A C14 H14 125.0 . . ?
C15 C14 H14 125.0 . . ?
N11A C15 C14 106.04(15) . . ?
N11A C15 H15 127.0 . . ?
C14 C15 H15 127.0 . . ?
C26 N21 C22 116.07(15) . . ?
N21 C22 C23 121.43(15) . . ?
N21 C22 C12 117.95(14) . . ?
C23 C22 C12 120.62(15) . . ?
N24 C23 C22 122.07(16) . . ?
N24 C23 H23 119.0 . . ?
C22 C23 H23 119.0 . . ?
C23 N24 C25 116.56(16) . . ?
C23 N24 I33 133.34(12) . . ?
C25 N24 I33 110.03(12) . . ?
N24 C25 C26 121.36(17) . . ?
N24 C25 H25 119.3 . . ?
C26 C25 H25 119.3 . . ?
N21 C26 C25 122.47(17) . . ?
N21 C26 H26 118.8 . . ?
C25 C26 H26 118.8 . . ?
C32 C31 C32 117.8(2) 3_656 . ?
C32 C31 I31 121.12(11) 3_656 . ?
C32 C31 I31 121.12(11) . . ?
F32 C32 C31 118.83(16) . . ?
F32 C32 C33 118.53(16) . . ?
C31 C32 C33 122.64(17) . . ?
C34 C33 C32 116.56(17) . . ?
C34 C33 I33 119.45(13) . . ?
C32 C33 I33 123.99(13) . . ?
C33 I33 N24 164.66(6) . . ?
F34 C34 C33 118.11(11) . . ?
F34 C34 C33 118.11(11) . 3_656 ?
C33 C34 C33 123.8(2) . 3_656 ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C15 N11A C12 N13A 0.23(19) . . . . ?
C15 N11A C12 C22 179.56(15) . . . . ?
N11A C12 N13A C14 -0.48(19) . . . . ?
C22 C12 N13A C14 -179.80(15) . . . . ?
C12 N13A C14 C15 0.6(2) . . . . ?
C12 N11A C15 C14 0.13(19) . . . . ?
N13A C14 C15 N11A -0.4(2) . . . . ?
C26 N21 C22 C23 1.5(3) . . . . ?
C26 N21 C22 C12 -177.82(15) . . . . ?
N13A C12 C22 N21 178.53(16) . . . . ?
N11A C12 C22 N21 -0.7(2) . . . . ?
N13A C12 C22 C23 -0.8(3) . . . . ?
N11A C12 C22 C23 179.98(16) . . . . ?
N21 C22 C23 N24 -2.2(3) . . . . ?
C12 C22 C23 N24 177.12(16) . . . . ?
C22 C23 N24 C25 0.9(3) . . . . ?
C22 C23 N24 I33 -175.41(12) . . . . ?
C23 N24 C25 C26 0.8(3) . . . . ?
I33 N24 C25 C26 177.95(15) . . . . ?
C22 N21 C26 C25 0.2(3) . . . . ?
N24 C25 C26 N21 -1.4(3) . . . . ?
C32 C31 C32 F32 178.85(18) 3_656 . . . ?
I31 C31 C32 F32 -1.15(18) . . . . ?
C32 C31 C32 C33 -1.26(12) 3_656 . . . ?
I31 C31 C32 C33 178.74(12) . . . . ?
F32 C32 C33 C34 -177.72(13) . . . . ?
C31 C32 C33 C34 2.4(2) . . . . ?
F32 C32 C33 I33 2.2(2) . . . . ?
C31 C32 C33 I33 -177.66(10) . . . . ?
C32 C33 C34 F34 178.85(11) . . . . ?
I33 C33 C34 F34 -1.09(13) . . . . ?
C32 C33 C34 C33 -1.15(11) . . . 3_656 ?
I33 C33 C34 C33 178.91(13) . . . 3_656 ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N11A H11 N13A 0.88 1.91 2.7823(18) 170.6 8_755
N13B H13 N11B 0.88 1.93 2.7823(18) 161.9 8_765

_diffrn_measured_fraction_theta_max 0.983
_diffrn_reflns_theta_full        32.52
_diffrn_measured_fraction_theta_full 0.983
_refine_diff_density_max         0.684
_refine_diff_density_min         -0.719
_refine_diff_density_rms         0.099
_database_code_depnum_ccdc_archive 'CCDC 994326'
#######################################################################
#
#                 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_A4D10

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
TW-1-69 [2-(2-pyrazinyl)-imidazole]2, 4,4'-diiodo-F8-biphenyl
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         
;
(C7 H6 N4)2 (C12 F8 I2)
;
_chemical_formula_sum            'C26 H12 F8 I2 N8'
_chemical_formula_weight         842.24

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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                   7.6527(4)
_cell_length_b                   12.7331(7)
_cell_length_c                   15.4446(9)
_cell_angle_alpha                67.3200(10)
_cell_angle_beta                 88.558(2)
_cell_angle_gamma                81.6160(10)
_cell_volume                     1372.95(13)
_cell_formula_units_Z            2
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    9485
_cell_measurement_theta_min      2.66
_cell_measurement_theta_max      33.35

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.22
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.037
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             804
_exptl_absorpt_coefficient_mu    2.380
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5164
_exptl_absorpt_correction_T_max  0.6226
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      120(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            40305
_diffrn_reflns_av_R_equivalents  0.0214
_diffrn_reflns_av_sigmaI/netI    0.0201
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         1.75
_diffrn_reflns_theta_max         33.45
_reflns_number_total             9826
_reflns_number_gt                9163
_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)+(0.0250P)²+0.7000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         9826
_refine_ls_number_parameters     403
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0234
_refine_ls_R_factor_gt           0.0210
_refine_ls_wR_factor_ref         0.0516
_refine_ls_wR_factor_gt          0.0505
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_restrained_S_all      1.041
_refine_ls_shift/su_max          0.004
_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
N11 N 0.24184(19) 1.17890(11) 0.00542(9) 0.0222(2) Uani 1 1 d . . .
H11 H 0.185(3) 1.2354(19) -0.0395(16) 0.027 Uiso 1 1 d . . .
C12 C 0.25510(19) 1.06869(12) 0.01225(10) 0.0188(2) Uani 1 1 d . . .
N13 N 0.33312(18) 0.99572(11) 0.09334(9) 0.0224(2) Uani 1 1 d . . .
C14 C 0.3703(2) 1.06354(14) 0.13962(11) 0.0258(3) Uani 1 1 d . . .
H14 H 0.4266 1.0355 0.2001 0.031 Uiso 1 1 calc R . .
C15 C 0.3148(2) 1.17681(13) 0.08628(11) 0.0259(3) Uani 1 1 d . . .
H15 H 0.3247 1.2409 0.1020 0.031 Uiso 1 1 calc R . .
N21 N 0.12747(18) 1.12081(11) -0.14245(9) 0.0223(2) Uani 1 1 d . . .
C22 C 0.19486(18) 1.03662(12) -0.06161(10) 0.0183(2) Uani 1 1 d . . .
C23 C 0.2065(2) 0.92131(13) -0.04926(11) 0.0267(3) Uani 1 1 d . . .
H23 H 0.2533 0.8638 0.0088 0.032 Uiso 1 1 calc R . .
N24 N 0.1551(2) 0.88841(12) -0.11523(10) 0.0280(3) Uani 1 1 d . . .
C25 C 0.0892(2) 0.97212(14) -0.19496(11) 0.0264(3) Uani 1 1 d . . .
H25 H 0.0515 0.9527 -0.2443 0.032 Uiso 1 1 calc R . .
C26 C 0.0743(2) 1.08691(14) -0.20781(11) 0.0266(3) Uani 1 1 d . . .
H26 H 0.0241 1.1437 -0.2654 0.032 Uiso 1 1 calc R . .
N31 N 1.08176(16) -0.63128(11) 0.73693(9) 0.0190(2) Uani 1 1 d . . .
H31 H 1.102(3) -0.6970(19) 0.7795(15) 0.023 Uiso 1 1 d . . .
C32 C 0.99131(17) -0.53396(11) 0.74208(9) 0.0165(2) Uani 1 1 d . . .
N33 N 0.98639(16) -0.44514(10) 0.66077(8) 0.0187(2) Uani 1 1 d . . .
C34 C 1.07857(19) -0.48785(13) 0.60083(10) 0.0208(3) Uani 1 1 d . . .
H34 H 1.0984 -0.4439 0.5369 0.025 Uiso 1 1 calc R . .
C35 C 1.13761(19) -0.60296(13) 0.64674(10) 0.0213(3) Uani 1 1 d . . .
H35 H 1.2037 -0.6529 0.6213 0.026 Uiso 1 1 calc R . .
N41 N 0.95767(18) -0.62467(11) 0.90795(9) 0.0224(2) Uani 1 1 d . . .
C42 C 0.91019(18) -0.53250(11) 0.82824(10) 0.0171(2) Uani 1 1 d . . .
C43 C 0.7845(2) -0.44110(13) 0.82766(11) 0.0227(3) Uani 1 1 d . . .
H43 H 0.7580 -0.3760 0.7705 0.027 Uiso 1 1 calc R . .
N44 N 0.7004(2) -0.44187(12) 0.90434(10) 0.0285(3) Uani 1 1 d . . .
C45 C 0.7445(2) -0.53515(14) 0.98290(11) 0.0281(3) Uani 1 1 d . . .
H45 H 0.6853 -0.5403 1.0389 0.034 Uiso 1 1 calc R . .
C46 C 0.8738(2) -0.62450(13) 0.98503(11) 0.0270(3) Uani 1 1 d . . .
H46 H 0.9038 -0.6876 1.0430 0.032 Uiso 1 1 calc R . .
C51 C 0.47984(18) 0.57690(11) 0.27189(10) 0.0169(2) Uani 1 1 d . . .
I1 I 0.411680(12) 0.754736(7) 0.200599(6) 0.01908(3) Uani 1 1 d . . .
C52 C 0.58784(18) 0.51310(12) 0.23067(9) 0.0172(2) Uani 1 1 d . . .
F52 F 0.64749(13) 0.56529(8) 0.14413(6) 0.02303(17) Uani 1 1 d . . .
C53 C 0.63785(18) 0.39571(12) 0.27648(9) 0.0169(2) Uani 1 1 d . . .
F53 F 0.74682(12) 0.33993(7) 0.23353(6) 0.02207(17) Uani 1 1 d . . .
C54 C 0.58111(17) 0.33558(11) 0.36612(9) 0.0157(2) Uani 1 1 d . . .
C55 C 0.47321(18) 0.40054(12) 0.40721(9) 0.0165(2) Uani 1 1 d . . .
F55 F 0.41374(12) 0.34901(8) 0.49354(6) 0.02107(16) Uani 1 1 d . . .
C56 C 0.42341(17) 0.51781(12) 0.36105(10) 0.0170(2) Uani 1 1 d . . .
F56 F 0.31823(12) 0.57406(8) 0.40481(7) 0.02307(17) Uani 1 1 d . . .
C61 C 0.75749(18) -0.02895(12) 0.50795(10) 0.0183(2) Uani 1 1 d . . .
I2 I 0.855056(11) -0.204345(7) 0.576606(6) 0.01970(3) Uani 1 1 d . . .
C62 C 0.77122(19) 0.04799(12) 0.54991(10) 0.0197(2) Uani 1 1 d . . .
F62 F 0.84668(15) 0.01076(9) 0.63605(7) 0.0317(2) Uani 1 1 d . . .
C63 C 0.71313(18) 0.16445(12) 0.50521(10) 0.0182(2) Uani 1 1 d . . .
F63 F 0.74041(13) 0.23361(8) 0.54862(6) 0.02429(18) Uani 1 1 d . . .
C64 C 0.63639(17) 0.21047(11) 0.41536(9) 0.0157(2) Uani 1 1 d . . .
C65 C 0.61944(17) 0.13279(11) 0.37375(9) 0.0165(2) Uani 1 1 d . . .
F65 F 0.53994(13) 0.17022(8) 0.28863(6) 0.02266(17) Uani 1 1 d . . .
C66 C 0.67884(18) 0.01623(12) 0.41888(10) 0.0179(2) Uani 1 1 d . . .
F66 F 0.65575(13) -0.05353(8) 0.37452(7) 0.02473(18) 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
N11 C12 1.3549(19) . ?
N11 C15 1.370(2) . ?
N11 H11 0.85(2) . ?
C12 N13 1.3293(18) . ?
C12 C22 1.456(2) . ?
N13 C14 1.377(2) . ?
N13 I1 2.8484(12) . ?
C14 C15 1.365(2) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
N21 C26 1.334(2) . ?
N21 C22 1.3465(18) . ?
C22 C23 1.395(2) . ?
C23 N24 1.329(2) . ?
C23 H23 0.9500 . ?
N24 C25 1.330(2) . ?
C25 C26 1.385(2) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?
N31 C32 1.3579(18) . ?
N31 C35 1.3714(19) . ?
N31 H31 0.84(2) . ?
C32 N33 1.3237(17) . ?
C32 C42 1.4597(19) . ?
N33 C34 1.3761(19) . ?
N33 I2 2.8625(12) . ?
C34 C35 1.370(2) . ?
C34 H34 0.9500 . ?
C35 H35 0.9500 . ?
N41 C46 1.339(2) . ?
N41 C42 1.3450(18) . ?
C42 C43 1.3948(19) . ?
C43 N44 1.331(2) . ?
C43 H43 0.9500 . ?
N44 C45 1.337(2) . ?
C45 C46 1.385(2) . ?
C45 H45 0.9500 . ?
C46 H46 0.9500 . ?
C51 C56 1.3836(19) . ?
C51 C52 1.3875(19) . ?
C51 I1 2.0914(13) . ?
C52 F52 1.3450(16) . ?
C52 C53 1.3829(19) . ?
C53 F53 1.3427(15) . ?
C53 C54 1.3931(18) . ?
C54 C55 1.3958(18) . ?
C54 C64 1.4766(19) . ?
C55 F55 1.3405(15) . ?
C55 C56 1.3820(19) . ?
C56 F56 1.3400(15) . ?
C61 C62 1.383(2) . ?
C61 C66 1.384(2) . ?
C61 I2 2.0969(13) . ?
C62 F62 1.3420(16) . ?
C62 C63 1.3809(19) . ?
C63 F63 1.3359(16) . ?
C63 C64 1.3884(19) . ?
C64 C65 1.3928(19) . ?
C65 F65 1.3410(15) . ?
C65 C66 1.3845(19) . ?
C66 F66 1.3455(16) . ?

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
C12 N11 C15 107.59(12) . . ?
C12 N11 H11 122.9(15) . . ?
C15 N11 H11 129.1(15) . . ?
N13 C12 N11 111.15(13) . . ?
N13 C12 C22 125.27(13) . . ?
N11 C12 C22 123.56(13) . . ?
C12 N13 C14 105.21(12) . . ?
C12 N13 I1 140.10(10) . . ?
C14 N13 I1 114.36(9) . . ?
C15 C14 N13 110.29(14) . . ?
C15 C14 H14 124.9 . . ?
N13 C14 H14 124.9 . . ?
C14 C15 N11 105.75(13) . . ?
C14 C15 H15 127.1 . . ?
N11 C15 H15 127.1 . . ?
C26 N21 C22 116.20(13) . . ?
N21 C22 C23 120.50(14) . . ?
N21 C22 C12 118.55(13) . . ?
C23 C22 C12 120.95(13) . . ?
N24 C23 C22 122.86(14) . . ?
N24 C23 H23 118.6 . . ?
C22 C23 H23 118.6 . . ?
C23 N24 C25 116.24(14) . . ?
N24 C25 C26 121.61(15) . . ?
N24 C25 H25 119.2 . . ?
C26 C25 H25 119.2 . . ?
N21 C26 C25 122.57(14) . . ?
N21 C26 H26 118.7 . . ?
C25 C26 H26 118.7 . . ?
C32 N31 C35 107.12(12) . . ?
C32 N31 H31 128.3(14) . . ?
C35 N31 H31 124.6(14) . . ?
N33 C32 N31 111.65(12) . . ?
N33 C32 C42 126.14(12) . . ?
N31 C32 C42 122.21(12) . . ?
C32 N33 C34 105.22(12) . . ?
C32 N33 I2 140.81(10) . . ?
C34 N33 I2 113.96(9) . . ?
C35 C34 N33 110.16(12) . . ?
C35 C34 H34 124.9 . . ?
N33 C34 H34 124.9 . . ?
C34 C35 N31 105.85(13) . . ?
C34 C35 H35 127.1 . . ?
N31 C35 H35 127.1 . . ?
C46 N41 C42 116.13(13) . . ?
N41 C42 C43 121.26(13) . . ?
N41 C42 C32 117.21(12) . . ?
C43 C42 C32 121.50(12) . . ?
N44 C43 C42 122.30(14) . . ?
N44 C43 H43 118.8 . . ?
C42 C43 H43 118.8 . . ?
C43 N44 C45 116.20(14) . . ?
N44 C45 C46 121.96(14) . . ?
N44 C45 H45 119.0 . . ?
C46 C45 H45 119.0 . . ?
N41 C46 C45 122.07(14) . . ?
N41 C46 H46 119.0 . . ?
C45 C46 H46 119.0 . . ?
C56 C51 C52 117.05(12) . . ?
C56 C51 I1 122.73(10) . . ?
C52 C51 I1 120.22(10) . . ?
C51 I1 N13 176.11(5) . . ?
F52 C52 C53 118.23(12) . . ?
F52 C52 C51 120.06(12) . . ?
C53 C52 C51 121.71(12) . . ?
F53 C53 C52 118.54(12) . . ?
F53 C53 C54 119.88(12) . . ?
C52 C53 C54 121.57(12) . . ?
C53 C54 C55 116.32(12) . . ?
C53 C54 C64 121.48(12) . . ?
C55 C54 C64 122.18(12) . . ?
F55 C55 C56 118.23(12) . . ?
F55 C55 C54 119.91(12) . . ?
C56 C55 C54 121.86(12) . . ?
F56 C56 C55 118.35(12) . . ?
F56 C56 C51 120.16(12) . . ?
C55 C56 C51 121.49(12) . . ?
C62 C61 C66 116.61(12) . . ?
C62 C61 I2 120.96(10) . . ?
C66 C61 I2 122.42(11) . . ?
C61 I2 N33 176.87(5) . . ?
F62 C62 C63 117.67(13) . . ?
F62 C62 C61 120.09(12) . . ?
C63 C62 C61 122.22(13) . . ?
F63 C63 C62 118.36(12) . . ?
F63 C63 C64 120.15(12) . . ?
C62 C63 C64 121.42(13) . . ?
C63 C64 C65 116.41(12) . . ?
C63 C64 C54 121.35(12) . . ?
C65 C64 C54 122.22(12) . . ?
F65 C65 C66 118.37(12) . . ?
F65 C65 C64 119.81(12) . . ?
C66 C65 C64 121.80(12) . . ?
F66 C66 C61 120.19(12) . . ?
F66 C66 C65 118.27(12) . . ?
C61 C66 C65 121.52(13) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C15 N11 C12 N13 -0.09(18) . . . . ?
C15 N11 C12 C22 -178.63(14) . . . . ?
N11 C12 N13 C14 0.09(18) . . . . ?
C22 C12 N13 C14 178.60(14) . . . . ?
N11 C12 N13 I1 172.64(11) . . . . ?
C22 C12 N13 I1 -8.8(3) . . . . ?
C12 N13 C14 C15 -0.05(19) . . . . ?
I1 N13 C14 C15 -174.82(11) . . . . ?
N13 C14 C15 N11 0.0(2) . . . . ?
C12 N11 C15 C14 0.06(18) . . . . ?
C26 N21 C22 C23 0.0(2) . . . . ?
C26 N21 C22 C12 179.99(14) . . . . ?
N13 C12 C22 N21 -176.09(14) . . . . ?
N11 C12 C22 N21 2.2(2) . . . . ?
N13 C12 C22 C23 3.9(2) . . . . ?
N11 C12 C22 C23 -177.79(15) . . . . ?
N21 C22 C23 N24 0.8(3) . . . . ?
C12 C22 C23 N24 -179.16(16) . . . . ?
C22 C23 N24 C25 -0.6(3) . . . . ?
C23 N24 C25 C26 -0.4(3) . . . . ?
C22 N21 C26 C25 -1.0(2) . . . . ?
N24 C25 C26 N21 1.3(3) . . . . ?
C35 N31 C32 N33 -0.17(17) . . . . ?
C35 N31 C32 C42 179.17(13) . . . . ?
N31 C32 N33 C34 -0.13(16) . . . . ?
C42 C32 N33 C34 -179.44(13) . . . . ?
N31 C32 N33 I2 -178.91(10) . . . . ?
C42 C32 N33 I2 1.8(2) . . . . ?
C32 N33 C34 C35 0.38(17) . . . . ?
I2 N33 C34 C35 179.54(10) . . . . ?
N33 C34 C35 N31 -0.49(17) . . . . ?
C32 N31 C35 C34 0.40(17) . . . . ?
C46 N41 C42 C43 1.9(2) . . . . ?
C46 N41 C42 C32 -176.12(14) . . . . ?
N33 C32 C42 N41 -167.43(14) . . . . ?
N31 C32 C42 N41 13.3(2) . . . . ?
N33 C32 C42 C43 14.5(2) . . . . ?
N31 C32 C42 C43 -164.70(14) . . . . ?
N41 C42 C43 N44 -2.6(2) . . . . ?
C32 C42 C43 N44 175.31(15) . . . . ?
C42 C43 N44 C45 0.7(3) . . . . ?
C43 N44 C45 C46 1.7(3) . . . . ?
C42 N41 C46 C45 0.5(2) . . . . ?
N44 C45 C46 N41 -2.5(3) . . . . ?
C56 C51 C52 F52 -179.92(12) . . . . ?
I1 C51 C52 F52 -0.77(18) . . . . ?
C56 C51 C52 C53 -0.3(2) . . . . ?
I1 C51 C52 C53 178.90(11) . . . . ?
F52 C52 C53 F53 1.6(2) . . . . ?
C51 C52 C53 F53 -178.07(13) . . . . ?
F52 C52 C53 C54 -179.85(13) . . . . ?
C51 C52 C53 C54 0.5(2) . . . . ?
F53 C53 C54 C55 177.78(12) . . . . ?
C52 C53 C54 C55 -0.7(2) . . . . ?
F53 C53 C54 C64 -0.7(2) . . . . ?
C52 C53 C54 C64 -179.26(13) . . . . ?
C53 C54 C55 F55 -179.73(12) . . . . ?
C64 C54 C55 F55 -1.2(2) . . . . ?
C53 C54 C55 C56 0.9(2) . . . . ?
C64 C54 C55 C56 179.35(13) . . . . ?
F55 C55 C56 F56 -0.03(19) . . . . ?
C54 C55 C56 F56 179.39(12) . . . . ?
F55 C55 C56 C51 179.89(12) . . . . ?
C54 C55 C56 C51 -0.7(2) . . . . ?
C52 C51 C56 F56 -179.73(12) . . . . ?
I1 C51 C56 F56 1.14(18) . . . . ?
C52 C51 C56 C55 0.4(2) . . . . ?
I1 C51 C56 C55 -178.78(10) . . . . ?
C66 C61 C62 F62 -179.67(13) . . . . ?
I2 C61 C62 F62 -0.47(19) . . . . ?
C66 C61 C62 C63 -1.3(2) . . . . ?
I2 C61 C62 C63 177.95(11) . . . . ?
F62 C62 C63 F63 2.2(2) . . . . ?
C61 C62 C63 F63 -176.28(13) . . . . ?
F62 C62 C63 C64 178.86(13) . . . . ?
C61 C62 C63 C64 0.4(2) . . . . ?
F63 C63 C64 C65 177.42(12) . . . . ?
C62 C63 C64 C65 0.8(2) . . . . ?
F63 C63 C64 C54 -0.8(2) . . . . ?
C62 C63 C64 C54 -177.42(13) . . . . ?
C53 C54 C64 C63 126.79(15) . . . . ?
C55 C54 C64 C63 -51.64(19) . . . . ?
C53 C54 C64 C65 -51.33(19) . . . . ?
C55 C54 C64 C65 130.24(15) . . . . ?
C63 C64 C65 F65 177.24(12) . . . . ?
C54 C64 C65 F65 -4.6(2) . . . . ?
C63 C64 C65 C66 -1.1(2) . . . . ?
C54 C64 C65 C66 177.07(13) . . . . ?
C62 C61 C66 F66 -177.98(13) . . . . ?
I2 C61 C66 F66 2.83(19) . . . . ?
C62 C61 C66 C65 0.9(2) . . . . ?
I2 C61 C66 C65 -178.28(10) . . . . ?
F65 C65 C66 F66 0.81(19) . . . . ?
C64 C65 C66 F66 179.20(12) . . . . ?
F65 C65 C66 C61 -178.11(13) . . . . ?
C64 C65 C66 C61 0.3(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N11 H11 N41 0.85(2) 2.22(2) 2.9877(18) 150(2) 1_474
N31 H31 N21 0.84(2) 2.14(2) 2.9552(18) 163(2) 1_636

_diffrn_measured_fraction_theta_max 0.915
_diffrn_reflns_theta_full        30.00
_diffrn_measured_fraction_theta_full 0.987
_refine_diff_density_max         0.646
_refine_diff_density_min         -0.545
_refine_diff_density_rms         0.089

#END
_database_code_depnum_ccdc_archive 'CCDC 994327'
