# 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_A8D2

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
DW-10-7 (3-pyridyl)-CONH-(CH2)8-NHCO-(3-pyridyl), I-(CF2)2-I
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         
;
(C20 H26 N4 O2) (C2 F4 I2)
;
_chemical_formula_sum            'C22 H26 F4 I2 N4 O2'
_chemical_formula_weight         708.27

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

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

_cell_length_a                   5.0587(4)
_cell_length_b                   5.0974(4)
_cell_length_c                   24.1635(19)
_cell_angle_alpha                84.859(2)
_cell_angle_beta                 84.330(2)
_cell_angle_gamma                88.194(2)
_cell_volume                     617.38(8)
_cell_formula_units_Z            1
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    9952
_cell_measurement_theta_min      3.40
_cell_measurement_theta_max      32.54

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.905
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             344
_exptl_absorpt_coefficient_mu    2.604
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4541
_exptl_absorpt_correction_T_max  0.8187
_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            15075
_diffrn_reflns_av_R_equivalents  0.0289
_diffrn_reflns_av_sigmaI/netI    0.0237
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_theta_min         1.70
_diffrn_reflns_theta_max         32.56
_reflns_number_total             4054
_reflns_number_gt                3877
_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+1.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4054
_refine_ls_number_parameters     157
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0235
_refine_ls_R_factor_gt           0.0219
_refine_ls_wR_factor_ref         0.0599
_refine_ls_wR_factor_gt          0.0563
_refine_ls_goodness_of_fit_ref   0.989
_refine_ls_restrained_S_all      0.989
_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 0.0145(4) 0.3904(4) 0.18699(7) 0.0314(4) Uani 1 1 d . . .
C12 C 0.1399(4) 0.4235(4) 0.23199(8) 0.0258(4) Uani 1 1 d . . .
H12 H 0.2795 0.3028 0.2409 0.031 Uiso 1 1 calc R . .
C13 C 0.0766(4) 0.6256(3) 0.26655(7) 0.0206(3) Uani 1 1 d . . .
C14 C -0.1296(4) 0.8003(4) 0.25360(8) 0.0252(3) Uani 1 1 d . . .
H14 H -0.1784 0.9415 0.2760 0.030 Uiso 1 1 calc R . .
C15 C -0.2626(4) 0.7645(5) 0.20749(9) 0.0313(4) Uani 1 1 d . . .
H15 H -0.4057 0.8796 0.1980 0.038 Uiso 1 1 calc R . .
C16 C -0.1845(5) 0.5599(5) 0.17557(9) 0.0314(4) Uani 1 1 d . . .
H16 H -0.2762 0.5379 0.1439 0.038 Uiso 1 1 calc R . .
C17 C 0.2314(4) 0.6701(3) 0.31420(7) 0.0203(3) Uani 1 1 d . . .
N17 N 0.3509(3) 0.4596(3) 0.33913(7) 0.0224(3) Uani 1 1 d . . .
H17 H 0.317(6) 0.320(6) 0.3304(12) 0.027 Uiso 1 1 d . . .
O17 O 0.2485(3) 0.8938(3) 0.32929(6) 0.0284(3) Uani 1 1 d . . .
C21 C 0.5152(4) 0.4883(4) 0.38429(8) 0.0223(3) Uani 1 1 d . . .
H21A H 0.4044 0.5577 0.4161 0.027 Uiso 1 1 calc R . .
H21B H 0.6556 0.6169 0.3714 0.027 Uiso 1 1 calc R . .
C22 C 0.6430(4) 0.2277(3) 0.40360(8) 0.0223(3) Uani 1 1 d . . .
H22A H 0.7603 0.1627 0.3722 0.027 Uiso 1 1 calc R . .
H22B H 0.5027 0.0968 0.4146 0.027 Uiso 1 1 calc R . .
C23 C 0.8047(4) 0.2517(3) 0.45270(8) 0.0217(3) Uani 1 1 d . . .
H23A H 0.9518 0.3741 0.4408 0.026 Uiso 1 1 calc R . .
H23B H 0.6899 0.3284 0.4830 0.026 Uiso 1 1 calc R . .
C24 C 0.9199(4) -0.0115(3) 0.47517(8) 0.0219(3) Uani 1 1 d . . .
H24A H 1.0361 -0.0872 0.4449 0.026 Uiso 1 1 calc R . .
H24B H 0.7729 -0.1344 0.4867 0.026 Uiso 1 1 calc R . .
C31 C 0.4452(5) -0.0949(4) 0.02462(8) 0.0288(4) Uani 1 1 d . . .
I1 I 0.26011(3) 0.10736(3) 0.093687(5) 0.02965(5) Uani 1 1 d . . .
F31A F 0.6460(3) -0.2500(3) 0.04175(6) 0.0413(3) Uani 1 1 d . . .
F31B F 0.2654(3) -0.2473(3) 0.00657(6) 0.0406(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 1.337(3) . ?
N11 C16 1.339(3) . ?
N11 I1 2.9366(19) . ?
C12 C13 1.394(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.391(3) . ?
C13 C17 1.492(2) . ?
C14 C15 1.385(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.377(3) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 O17 1.236(2) . ?
C17 N17 1.340(2) . ?
N17 C21 1.456(2) . ?
N17 H17 0.79(3) . ?
C21 C22 1.515(2) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 C23 1.522(2) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 C24 1.522(2) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C24 C24 1.527(3) 2_756 ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C31 F31A 1.342(3) . ?
C31 F31B 1.343(3) . ?
C31 C31 1.535(4) 2_655 ?
C31 I1 2.160(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
C12 N11 C16 117.45(18) . . ?
C12 N11 I1 122.53(15) . . ?
C16 N11 I1 116.33(13) . . ?
N11 C12 C13 123.50(19) . . ?
N11 C12 H12 118.3 . . ?
C13 C12 H12 118.3 . . ?
C14 C13 C12 117.97(17) . . ?
C14 C13 C17 119.37(16) . . ?
C12 C13 C17 122.55(17) . . ?
C15 C14 C13 118.74(19) . . ?
C15 C14 H14 120.6 . . ?
C13 C14 H14 120.6 . . ?
C16 C15 C14 119.1(2) . . ?
C16 C15 H15 120.5 . . ?
C14 C15 H15 120.5 . . ?
N11 C16 C15 123.23(19) . . ?
N11 C16 H16 118.4 . . ?
C15 C16 H16 118.4 . . ?
O17 C17 N17 122.07(17) . . ?
O17 C17 C13 120.58(16) . . ?
N17 C17 C13 117.35(15) . . ?
C17 N17 C21 120.68(15) . . ?
C17 N17 H17 117(2) . . ?
C21 N17 H17 122(2) . . ?
N17 C21 C22 111.38(14) . . ?
N17 C21 H21A 109.4 . . ?
C22 C21 H21A 109.4 . . ?
N17 C21 H21B 109.4 . . ?
C22 C21 H21B 109.4 . . ?
H21A C21 H21B 108.0 . . ?
C21 C22 C23 112.04(14) . . ?
C21 C22 H22A 109.2 . . ?
C23 C22 H22A 109.2 . . ?
C21 C22 H22B 109.2 . . ?
C23 C22 H22B 109.2 . . ?
H22A C22 H22B 107.9 . . ?
C24 C23 C22 112.86(14) . . ?
C24 C23 H23A 109.0 . . ?
C22 C23 H23A 109.0 . . ?
C24 C23 H23B 109.0 . . ?
C22 C23 H23B 109.0 . . ?
H23A C23 H23B 107.8 . . ?
C23 C24 C24 113.02(18) . 2_756 ?
C23 C24 H24A 109.0 . . ?
C24 C24 H24A 109.0 2_756 . ?
C23 C24 H24B 109.0 . . ?
C24 C24 H24B 109.0 2_756 . ?
H24A C24 H24B 107.8 . . ?
F31A C31 F31B 108.45(17) . . ?
F31A C31 C31 108.5(2) . 2_655 ?
F31B C31 C31 108.4(2) . 2_655 ?
F31A C31 I1 109.55(13) . . ?
F31B C31 I1 109.11(15) . . ?
C31 C31 I1 112.75(18) 2_655 . ?
C31 I1 N11 178.98(7) . . ?

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 -1.0(3) . . . . ?
I1 N11 C12 C13 156.55(15) . . . . ?
N11 C12 C13 C14 0.6(3) . . . . ?
N11 C12 C13 C17 -175.60(19) . . . . ?
C12 C13 C14 C15 0.4(3) . . . . ?
C17 C13 C14 C15 176.67(18) . . . . ?
C13 C14 C15 C16 -0.9(3) . . . . ?
C12 N11 C16 C15 0.5(3) . . . . ?
I1 N11 C16 C15 -158.45(18) . . . . ?
C14 C15 C16 N11 0.4(3) . . . . ?
C14 C13 C17 O17 -25.8(3) . . . . ?
C12 C13 C17 O17 150.3(2) . . . . ?
C14 C13 C17 N17 154.79(18) . . . . ?
C12 C13 C17 N17 -29.1(3) . . . . ?
O17 C17 N17 C21 -2.2(3) . . . . ?
C13 C17 N17 C21 177.27(16) . . . . ?
C17 N17 C21 C22 -176.53(17) . . . . ?
N17 C21 C22 C23 -177.23(16) . . . . ?
C21 C22 C23 C24 176.26(16) . . . . ?
C22 C23 C24 C24 -179.4(2) . . . 2_756 ?

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
N17 H17 O17 0.79(3) 2.21(3) 2.980(2) 164(3) 1_545

_diffrn_measured_fraction_theta_max 0.903
_diffrn_reflns_theta_full        30.00
_diffrn_measured_fraction_theta_full 0.969
_refine_diff_density_max         0.745
_refine_diff_density_min         -0.833
_refine_diff_density_rms         0.096
_database_code_depnum_ccdc_archive 'CCDC 1011547'
#######################################################################
#
#                 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_A8D4

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
DW-10-8 (3-pyridyl)-CONH-(CH2)8-NHCO-(3-pyridyl), I-(CF2)4-I
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         
;
(C20 H26 N4 O2) (C4 F8 I2)
;
_chemical_formula_sum            'C24 H26 F8 I2 N4 O2'
_chemical_formula_weight         808.29

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

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

_cell_length_a                   5.0194(3)
_cell_length_b                   5.0906(3)
_cell_length_c                   26.5502(14)
_cell_angle_alpha                85.503(2)
_cell_angle_beta                 85.901(2)
_cell_angle_gamma                88.2190(10)
_cell_volume                     674.36(7)
_cell_formula_units_Z            1
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    9945
_cell_measurement_theta_min      2.31
_cell_measurement_theta_max      33.22

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.990
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             392
_exptl_absorpt_coefficient_mu    2.418
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5721
_exptl_absorpt_correction_T_max  0.7601
_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            15718
_diffrn_reflns_av_R_equivalents  0.0164
_diffrn_reflns_av_sigmaI/netI    0.0159
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_limit_l_max       40
_diffrn_reflns_theta_min         1.54
_diffrn_reflns_theta_max         33.14
_reflns_number_total             4765
_reflns_number_gt                4641
_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+0.4000P] 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         4765
_refine_ls_number_parameters     184
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0168
_refine_ls_R_factor_gt           0.0161
_refine_ls_wR_factor_ref         0.0414
_refine_ls_wR_factor_gt          0.0410
_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 0.5369(2) 0.1229(2) 0.28278(4) 0.0208(2) Uani 1 1 d . . .
C12 C 0.4031(3) 0.0869(2) 0.24223(5) 0.0177(2) Uani 1 1 d . . .
H12 H 0.2610 0.2072 0.2343 0.021 Uiso 1 1 calc R . .
C13 C 0.4608(2) -0.1172(2) 0.21103(4) 0.01420(19) Uani 1 1 d . . .
C14 C 0.6693(2) -0.2924(2) 0.22275(5) 0.0171(2) Uani 1 1 d . . .
H14 H 0.7139 -0.4354 0.2025 0.021 Uiso 1 1 calc R . .
C15 C 0.8110(3) -0.2551(3) 0.26440(5) 0.0203(2) Uani 1 1 d . . .
H15 H 0.9562 -0.3704 0.2729 0.024 Uiso 1 1 calc R . .
C16 C 0.7373(3) -0.0469(3) 0.29337(5) 0.0214(2) Uani 1 1 d . . .
H16 H 0.8337 -0.0234 0.3221 0.026 Uiso 1 1 calc R . .
C17 C 0.2980(2) -0.1644(2) 0.16788(4) 0.01419(19) Uani 1 1 d . . .
N17 N 0.1745(2) 0.0451(2) 0.14545(4) 0.01538(18) Uani 1 1 d . . .
H17 H 0.204(4) 0.193(4) 0.1525(7) 0.018 Uiso 1 1 d . . .
O17 O 0.2773(2) -0.38882(18) 0.15431(4) 0.01947(17) Uani 1 1 d . . .
C21 C 0.0020(2) 0.0141(2) 0.10463(5) 0.0154(2) Uani 1 1 d . . .
H21A H -0.1382 -0.1134 0.1165 0.018 Uiso 1 1 calc R . .
H21B H 0.1086 -0.0574 0.0757 0.018 Uiso 1 1 calc R . .
C22 C -0.1282(2) 0.2749(2) 0.08724(5) 0.0154(2) Uani 1 1 d . . .
H22A H 0.0122 0.4049 0.0772 0.019 Uiso 1 1 calc R . .
H22B H -0.2417 0.3417 0.1158 0.019 Uiso 1 1 calc R . .
C23 C -0.2983(2) 0.2491(2) 0.04274(5) 0.0153(2) Uani 1 1 d . . .
H23A H -0.1873 0.1701 0.0152 0.018 Uiso 1 1 calc R . .
H23B H -0.4458 0.1281 0.0536 0.018 Uiso 1 1 calc R . .
C24 C -0.4154(2) 0.5123(2) 0.02241(5) 0.0155(2) Uani 1 1 d . . .
H24A H -0.2678 0.6335 0.0118 0.019 Uiso 1 1 calc R . .
H24B H -0.5272 0.5906 0.0499 0.019 Uiso 1 1 calc R . .
C31 C 0.1330(3) 0.6212(2) 0.42932(5) 0.0171(2) Uani 1 1 d . . .
I1 I 0.306560(16) 0.412200(15) 0.366922(3) 0.01758(3) Uani 1 1 d . . .
F31A F -0.08659(18) 0.75549(18) 0.41502(3) 0.02551(17) Uani 1 1 d . . .
F31B F 0.30802(18) 0.79568(16) 0.44129(3) 0.02378(16) Uani 1 1 d . . .
C32 C 0.0591(2) 0.4327(2) 0.47623(5) 0.0152(2) Uani 1 1 d . . .
F32A F -0.12063(17) 0.26510(16) 0.46312(3) 0.02179(15) Uani 1 1 d . . .
F32B F 0.28069(16) 0.29577(16) 0.48856(3) 0.02075(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
N11 C12 1.3359(16) . ?
N11 C16 1.3365(19) . ?
N11 I1 2.9220(12) . ?
C12 C13 1.3894(17) . ?
C12 H12 0.9500 . ?
C13 C14 1.3902(17) . ?
C13 C17 1.4925(16) . ?
C14 C15 1.3852(18) . ?
C14 H14 0.9500 . ?
C15 C16 1.384(2) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 O17 1.2339(14) . ?
C17 N17 1.3374(15) . ?
N17 C21 1.4555(15) . ?
N17 H17 0.81(2) . ?
C21 C22 1.5152(17) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 C23 1.5226(16) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 C24 1.5214(17) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C24 C24 1.526(2) 2_465 ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C31 F31B 1.3393(15) . ?
C31 F31A 1.3413(15) . ?
C31 C32 1.5423(18) . ?
C31 I1 2.1559(12) . ?
C32 F32B 1.3409(14) . ?
C32 F32A 1.3425(14) . ?
C32 C32 1.555(2) 2_566 ?

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 C16 117.69(12) . . ?
C12 N11 I1 122.51(9) . . ?
C16 N11 I1 115.99(8) . . ?
N11 C12 C13 123.51(12) . . ?
N11 C12 H12 118.2 . . ?
C13 C12 H12 118.2 . . ?
C12 C13 C14 118.01(11) . . ?
C12 C13 C17 122.70(11) . . ?
C14 C13 C17 119.18(11) . . ?
C15 C14 C13 118.92(12) . . ?
C15 C14 H14 120.5 . . ?
C13 C14 H14 120.5 . . ?
C16 C15 C14 118.79(12) . . ?
C16 C15 H15 120.6 . . ?
C14 C15 H15 120.6 . . ?
N11 C16 C15 123.08(12) . . ?
N11 C16 H16 118.5 . . ?
C15 C16 H16 118.5 . . ?
O17 C17 N17 122.10(11) . . ?
O17 C17 C13 120.74(11) . . ?
N17 C17 C13 117.15(10) . . ?
C17 N17 C21 120.57(10) . . ?
C17 N17 H17 120.9(13) . . ?
C21 N17 H17 118.3(14) . . ?
N17 C21 C22 111.17(10) . . ?
N17 C21 H21A 109.4 . . ?
C22 C21 H21A 109.4 . . ?
N17 C21 H21B 109.4 . . ?
C22 C21 H21B 109.4 . . ?
H21A C21 H21B 108.0 . . ?
C21 C22 C23 111.92(10) . . ?
C21 C22 H22A 109.2 . . ?
C23 C22 H22A 109.2 . . ?
C21 C22 H22B 109.2 . . ?
C23 C22 H22B 109.2 . . ?
H22A C22 H22B 107.9 . . ?
C24 C23 C22 112.71(10) . . ?
C24 C23 H23A 109.1 . . ?
C22 C23 H23A 109.1 . . ?
C24 C23 H23B 109.1 . . ?
C22 C23 H23B 109.1 . . ?
H23A C23 H23B 107.8 . . ?
C23 C24 C24 112.93(12) . 2_465 ?
C23 C24 H24A 109.0 . . ?
C24 C24 H24A 109.0 2_465 . ?
C23 C24 H24B 109.0 . . ?
C24 C24 H24B 109.0 2_465 . ?
H24A C24 H24B 107.8 . . ?
F31B C31 F31A 107.89(10) . . ?
F31B C31 C32 109.41(10) . . ?
F31A C31 C32 109.41(10) . . ?
F31B C31 I1 108.95(8) . . ?
F31A C31 I1 109.26(8) . . ?
C32 C31 I1 111.84(8) . . ?
C31 I1 N11 179.21(4) . . ?
F32B C32 F32A 108.94(10) . . ?
F32B C32 C31 107.92(10) . . ?
F32A C32 C31 107.67(10) . . ?
F32B C32 C32 108.25(12) . 2_566 ?
F32A C32 C32 108.49(12) . 2_566 ?
C31 C32 C32 115.43(12) . 2_566 ?

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 0.4(2) . . . . ?
I1 N11 C12 C13 -156.74(10) . . . . ?
N11 C12 C13 C14 -0.13(19) . . . . ?
N11 C12 C13 C17 175.92(12) . . . . ?
C12 C13 C14 C15 -0.55(18) . . . . ?
C17 C13 C14 C15 -176.75(11) . . . . ?
C13 C14 C15 C16 0.98(19) . . . . ?
C12 N11 C16 C15 0.1(2) . . . . ?
I1 N11 C16 C15 158.68(11) . . . . ?
C14 C15 C16 N11 -0.8(2) . . . . ?
C12 C13 C17 O17 -150.25(12) . . . . ?
C14 C13 C17 O17 25.76(17) . . . . ?
C12 C13 C17 N17 28.87(17) . . . . ?
C14 C13 C17 N17 -155.12(11) . . . . ?
O17 C17 N17 C21 1.95(18) . . . . ?
C13 C17 N17 C21 -177.15(10) . . . . ?
C17 N17 C21 C22 176.67(11) . . . . ?
N17 C21 C22 C23 177.08(10) . . . . ?
C21 C22 C23 C24 -176.08(10) . . . . ?
C22 C23 C24 C24 179.63(12) . . . 2_465 ?
F31B C31 I1 N11 156(3) . . . . ?
F31A C31 I1 N11 -86(3) . . . . ?
C32 C31 I1 N11 35(3) . . . . ?
C12 N11 I1 C31 72(3) . . . . ?
C16 N11 I1 C31 -86(3) . . . . ?
F31B C31 C32 F32B -63.93(12) . . . . ?
F31A C31 C32 F32B 178.07(9) . . . . ?
I1 C31 C32 F32B 56.87(11) . . . . ?
F31B C31 C32 F32A 178.62(10) . . . . ?
F31A C31 C32 F32A 60.62(12) . . . . ?
I1 C31 C32 F32A -60.58(11) . . . . ?
F31B C31 C32 C32 57.28(16) . . . 2_566 ?
F31A C31 C32 C32 -60.71(16) . . . 2_566 ?
I1 C31 C32 C32 178.09(11) . . . 2_566 ?

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
N17 H17 O17 0.81(2) 2.18(2) 2.9736(14) 167.9(18) 1_565

_diffrn_measured_fraction_theta_max 0.926
_diffrn_reflns_theta_full        30.00
_diffrn_measured_fraction_theta_full 0.992
_refine_diff_density_max         0.561
_refine_diff_density_min         -0.309
_refine_diff_density_rms         0.067
_database_code_depnum_ccdc_archive 'CCDC 1011548'
#######################################################################
#
#                 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_A8D6

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
DW-10-9 (3-pyridyl)-CONH-(CH2)8-NHCO-(3-pyridyl),  I-(CF2)6-I
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         
;
(C20 H26 N4 O2) (C6 F12 I2)
;
_chemical_formula_sum            'C26 H26 F12 I2 N4 O2'
_chemical_formula_weight         908.31

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

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

_cell_length_a                   5.0345(12)
_cell_length_b                   5.1049(12)
_cell_length_c                   29.113(7)
_cell_angle_alpha                85.793(6)
_cell_angle_beta                 87.469(7)
_cell_angle_gamma                88.033(5)
_cell_volume                     745.1(3)
_cell_formula_units_Z            1
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    9901
_cell_measurement_theta_min      2.81
_cell_measurement_theta_max      34.97

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.024
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             440
_exptl_absorpt_coefficient_mu    2.219
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4418
_exptl_absorpt_correction_T_max  0.6908
_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            14798
_diffrn_reflns_av_R_equivalents  0.0476
_diffrn_reflns_av_sigmaI/netI    0.0417
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -45
_diffrn_reflns_limit_l_max       42
_diffrn_reflns_theta_min         2.81
_diffrn_reflns_theta_max         34.97
_reflns_number_total             5389
_reflns_number_gt                5266
_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+0.6000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5389
_refine_ls_number_parameters     211
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0287
_refine_ls_R_factor_gt           0.0281
_refine_ls_wR_factor_ref         0.0725
_refine_ls_wR_factor_gt          0.0720
_refine_ls_goodness_of_fit_ref   1.131
_refine_ls_restrained_S_all      1.131
_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 -0.0761(4) 0.3707(3) 0.24204(6) 0.0230(3) Uani 1 1 d . . .
C12 C 0.0637(4) 0.4074(3) 0.27900(6) 0.0195(3) Uani 1 1 d . . .
H12 H 0.2069 0.2875 0.2862 0.023 Uiso 1 1 calc R . .
C13 C 0.0098(3) 0.6130(3) 0.30742(6) 0.0151(3) Uani 1 1 d . . .
C14 C -0.2002(4) 0.7876(4) 0.29662(6) 0.0187(3) Uani 1 1 d . . .
H14 H -0.2419 0.9310 0.3150 0.022 Uiso 1 1 calc R . .
C15 C -0.3476(4) 0.7496(4) 0.25878(7) 0.0230(3) Uani 1 1 d . . .
H15 H -0.4934 0.8649 0.2510 0.028 Uiso 1 1 calc R . .
C16 C -0.2786(4) 0.5403(4) 0.23251(7) 0.0242(4) Uani 1 1 d . . .
H16 H -0.3798 0.5159 0.2065 0.029 Uiso 1 1 calc R . .
C17 C 0.1787(3) 0.6604(3) 0.34677(6) 0.0154(3) Uani 1 1 d . . .
N17 N 0.3049(3) 0.4511(3) 0.36729(5) 0.0173(3) Uani 1 1 d . . .
H17 H 0.272(6) 0.292(6) 0.3596(10) 0.021 Uiso 1 1 d . . .
O17 O 0.2011(3) 0.8848(3) 0.35918(5) 0.0217(3) Uani 1 1 d . . .
C21 C 0.4834(4) 0.4829(3) 0.40454(6) 0.0173(3) Uani 1 1 d . . .
H21A H 0.3813 0.5553 0.4308 0.021 Uiso 1 1 calc R . .
H21B H 0.6214 0.6094 0.3937 0.021 Uiso 1 1 calc R . .
C22 C 0.6158(4) 0.2231(3) 0.42037(6) 0.0180(3) Uani 1 1 d . . .
H22A H 0.7253 0.1556 0.3945 0.022 Uiso 1 1 calc R . .
H22B H 0.4773 0.0939 0.4295 0.022 Uiso 1 1 calc R . .
C23 C 0.7915(4) 0.2497(3) 0.46102(6) 0.0173(3) Uani 1 1 d . . .
H23A H 0.9366 0.3703 0.4512 0.021 Uiso 1 1 calc R . .
H23B H 0.6843 0.3289 0.4861 0.021 Uiso 1 1 calc R . .
C24 C 0.9125(4) -0.0129(3) 0.47955(6) 0.0177(3) Uani 1 1 d . . .
H24A H 1.0204 -0.0915 0.4545 0.021 Uiso 1 1 calc R . .
H24B H 0.7674 -0.1337 0.4891 0.021 Uiso 1 1 calc R . .
C31 C 0.3000(4) -0.1373(3) 0.10846(6) 0.0184(3) Uani 1 1 d . . .
I1 I 0.14003(2) 0.07685(2) 0.165224(3) 0.01946(4) Uani 1 1 d . . .
F31A F 0.1227(3) -0.3114(2) 0.09826(4) 0.0272(3) Uani 1 1 d . . .
F31B F 0.5225(3) -0.2702(3) 0.12095(5) 0.0296(3) Uani 1 1 d . . .
C32 C 0.3610(3) 0.0482(3) 0.06491(6) 0.0166(3) Uani 1 1 d . . .
F32A F 0.1364(2) 0.1817(2) 0.05405(4) 0.0228(2) Uani 1 1 d . . .
F32B F 0.5422(3) 0.2173(2) 0.07603(4) 0.0251(2) Uani 1 1 d . . .
C33 C 0.4709(3) -0.0935(3) 0.02193(6) 0.0164(3) Uani 1 1 d . . .
F33A F 0.2929(3) -0.2666(2) 0.01166(4) 0.0241(2) Uani 1 1 d . . .
F33B F 0.6979(3) -0.2237(2) 0.03313(4) 0.0247(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 1.339(2) . ?
N11 C16 1.340(3) . ?
N11 I1 2.9327(18) . ?
C12 C13 1.396(2) . ?
C12 H12 0.9500 . ?
C13 C14 1.391(2) . ?
C13 C17 1.495(2) . ?
C14 C15 1.384(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.385(3) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 O17 1.236(2) . ?
C17 N17 1.340(2) . ?
N17 C21 1.460(2) . ?
N17 H17 0.88(3) . ?
C21 C22 1.514(2) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 C23 1.525(2) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 C24 1.525(2) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C24 C24 1.528(3) 2_756 ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C31 F31A 1.338(2) . ?
C31 F31B 1.339(2) . ?
C31 C32 1.552(3) . ?
C31 I1 2.1593(18) . ?
C32 F32A 1.338(2) . ?
C32 F32B 1.343(2) . ?
C32 C33 1.562(2) . ?
C33 F33A 1.3379(19) . ?
C33 F33B 1.342(2) . ?
C33 C33 1.561(4) 2_655 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C12 N11 C16 117.62(16) . . ?
C12 N11 I1 122.62(13) . . ?
C16 N11 I1 116.08(12) . . ?
N11 C12 C13 123.31(17) . . ?
N11 C12 H12 118.3 . . ?
C13 C12 H12 118.3 . . ?
C14 C13 C12 117.99(15) . . ?
C14 C13 C17 119.44(15) . . ?
C12 C13 C17 122.46(15) . . ?
C15 C14 C13 119.10(17) . . ?
C15 C14 H14 120.4 . . ?
C13 C14 H14 120.4 . . ?
C14 C15 C16 118.76(18) . . ?
C14 C15 H15 120.6 . . ?
C16 C15 H15 120.6 . . ?
N11 C16 C15 123.21(17) . . ?
N11 C16 H16 118.4 . . ?
C15 C16 H16 118.4 . . ?
O17 C17 N17 122.12(15) . . ?
O17 C17 C13 120.69(15) . . ?
N17 C17 C13 117.18(14) . . ?
C17 N17 C21 120.46(14) . . ?
C17 N17 H17 120.0(19) . . ?
C21 N17 H17 119.4(19) . . ?
N17 C21 C22 111.11(13) . . ?
N17 C21 H21A 109.4 . . ?
C22 C21 H21A 109.4 . . ?
N17 C21 H21B 109.4 . . ?
C22 C21 H21B 109.4 . . ?
H21A C21 H21B 108.0 . . ?
C21 C22 C23 111.85(13) . . ?
C21 C22 H22A 109.2 . . ?
C23 C22 H22A 109.2 . . ?
C21 C22 H22B 109.2 . . ?
C23 C22 H22B 109.2 . . ?
H22A C22 H22B 107.9 . . ?
C24 C23 C22 112.72(13) . . ?
C24 C23 H23A 109.0 . . ?
C22 C23 H23A 109.0 . . ?
C24 C23 H23B 109.0 . . ?
C22 C23 H23B 109.0 . . ?
H23A C23 H23B 107.8 . . ?
C23 C24 C24 112.88(17) . 2_756 ?
C23 C24 H24A 109.0 . . ?
C24 C24 H24A 109.0 2_756 . ?
C23 C24 H24B 109.0 . . ?
C24 C24 H24B 109.0 2_756 . ?
H24A C24 H24B 107.8 . . ?
F31A C31 F31B 108.08(15) . . ?
F31A C31 C32 108.82(14) . . ?
F31B C31 C32 109.67(15) . . ?
F31A C31 I1 108.95(12) . . ?
F31B C31 I1 109.50(12) . . ?
C32 C31 I1 111.74(11) . . ?
C31 I1 N11 179.66(6) . . ?
F32A C32 F32B 109.20(14) . . ?
F32A C32 C31 108.04(14) . . ?
F32B C32 C31 107.36(14) . . ?
F32A C32 C33 108.79(13) . . ?
F32B C32 C33 108.62(14) . . ?
C31 C32 C33 114.72(14) . . ?
F33A C33 F33B 108.95(14) . . ?
F33A C33 C33 108.24(17) . 2_655 ?
F33B C33 C33 108.38(18) . 2_655 ?
F33A C33 C32 108.47(14) . . ?
F33B C33 C32 108.14(14) . . ?
C33 C33 C32 114.55(17) 2_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
C16 N11 C12 C13 -0.5(3) . . . . ?
I1 N11 C12 C13 157.01(14) . . . . ?
N11 C12 C13 C14 0.0(3) . . . . ?
N11 C12 C13 C17 -176.09(18) . . . . ?
C12 C13 C14 C15 0.6(3) . . . . ?
C17 C13 C14 C15 176.88(17) . . . . ?
C13 C14 C15 C16 -0.8(3) . . . . ?
C12 N11 C16 C15 0.3(3) . . . . ?
I1 N11 C16 C15 -158.69(16) . . . . ?
C14 C15 C16 N11 0.4(3) . . . . ?
C14 C13 C17 O17 -25.7(3) . . . . ?
C12 C13 C17 O17 150.37(18) . . . . ?
C14 C13 C17 N17 154.96(17) . . . . ?
C12 C13 C17 N17 -29.0(3) . . . . ?
O17 C17 N17 C21 -2.2(3) . . . . ?
C13 C17 N17 C21 177.10(16) . . . . ?
C17 N17 C21 C22 -176.54(17) . . . . ?
N17 C21 C22 C23 -176.91(15) . . . . ?
C21 C22 C23 C24 176.25(16) . . . . ?
C22 C23 C24 C24 -179.68(19) . . . 2_756 ?
F31A C31 C32 F32A 63.33(17) . . . . ?
F31B C31 C32 F32A -178.63(14) . . . . ?
I1 C31 C32 F32A -57.02(15) . . . . ?
F31A C31 C32 F32B -179.01(14) . . . . ?
F31B C31 C32 F32B -60.97(18) . . . . ?
I1 C31 C32 F32B 60.65(16) . . . . ?
F31A C31 C32 C33 -58.20(19) . . . . ?
F31B C31 C32 C33 59.84(18) . . . . ?
I1 C31 C32 C33 -178.55(11) . . . . ?
F32A C32 C33 F33A -62.77(18) . . . . ?
F32B C32 C33 F33A 178.46(14) . . . . ?
C31 C32 C33 F33A 58.35(19) . . . . ?
F32A C32 C33 F33B 179.21(14) . . . . ?
F32B C32 C33 F33B 60.44(18) . . . . ?
C31 C32 C33 F33B -59.67(18) . . . . ?
F32A C32 C33 C33 58.2(2) . . . 2_655 ?
F32B C32 C33 C33 -60.5(2) . . . 2_655 ?
C31 C32 C33 C33 179.37(17) . . . 2_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
N17 H17 O17 0.88(3) 2.12(3) 2.983(2) 166(3) 1_545

_diffrn_measured_fraction_theta_max 0.823
_diffrn_reflns_theta_full        30.00
_diffrn_measured_fraction_theta_full 0.965
_refine_diff_density_max         0.689
_refine_diff_density_min         -1.257
_refine_diff_density_rms         0.159
_database_code_depnum_ccdc_archive 'CCDC 1011549'
#######################################################################
#
#                 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_A6D2

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
DW-8-7 (3-pyridyl)-CONH-(CH2)6-NHCO-(3-pyridyl), I-(CF2)2-I
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         
;
(C18 H22 N4 O2) (C2 F4 I2)
;
_chemical_formula_sum            'C20 H22 F4 I2 N4 O2'
_chemical_formula_weight         680.22

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

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

_cell_length_a                   5.0593(7)
_cell_length_b                   5.0774(7)
_cell_length_c                   22.229(3)
_cell_angle_alpha                94.513(5)
_cell_angle_beta                 91.986(4)
_cell_angle_gamma                91.522(4)
_cell_volume                     568.65(14)
_cell_formula_units_Z            1
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    9932
_cell_measurement_theta_min      2.76
_cell_measurement_theta_max      33.13

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.14
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.986
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             328
_exptl_absorpt_coefficient_mu    2.823
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4653
_exptl_absorpt_correction_T_max  0.6933
_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            12442
_diffrn_reflns_av_R_equivalents  0.0247
_diffrn_reflns_av_sigmaI/netI    0.0214
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_theta_min         1.84
_diffrn_reflns_theta_max         32.57
_reflns_number_total             3612
_reflns_number_gt                3479
_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+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     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3612
_refine_ls_number_parameters     145
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0259
_refine_ls_R_factor_gt           0.0244
_refine_ls_wR_factor_ref         0.0752
_refine_ls_wR_factor_gt          0.0688
_refine_ls_goodness_of_fit_ref   1.183
_refine_ls_restrained_S_all      1.183
_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 0.0651(5) 0.4629(5) 0.29838(11) 0.0263(4) Uani 1 1 d . . .
C12 C 0.2041(5) 0.3931(5) 0.25005(11) 0.0201(4) Uani 1 1 d . . .
H12 H 0.3471 0.5058 0.2406 0.024 Uiso 1 1 calc R . .
C13 C 0.1500(4) 0.1634(4) 0.21271(10) 0.0164(4) Uani 1 1 d . . .
C14 C -0.0588(5) -0.0015(5) 0.22667(12) 0.0217(4) Uani 1 1 d . . .
H14 H -0.0996 -0.1614 0.2026 0.026 Uiso 1 1 calc R . .
C15 C -0.2062(5) 0.0712(6) 0.27618(12) 0.0251(5) Uani 1 1 d . . .
H15 H -0.3525 -0.0356 0.2863 0.030 Uiso 1 1 calc R . .
C16 C -0.1364(6) 0.3018(6) 0.31045(12) 0.0263(5) Uani 1 1 d . . .
H16 H -0.2372 0.3493 0.3447 0.032 Uiso 1 1 calc R . .
C17 C 0.3190(4) 0.0778(4) 0.16091(10) 0.0165(4) Uani 1 1 d . . .
N17 N 0.4455(4) 0.2701(4) 0.13409(9) 0.0185(4) Uani 1 1 d . . .
H17 H 0.4213 0.4369 0.1459 0.022 Uiso 1 1 calc R . .
O17 O 0.3409(4) -0.1580(3) 0.14469(9) 0.0235(4) Uani 1 1 d . . .
C21 C 0.6227(5) 0.2020(4) 0.08537(11) 0.0185(4) Uani 1 1 d . . .
H21A H 0.5204 0.1089 0.0509 0.022 Uiso 1 1 calc R . .
H21B H 0.7575 0.0806 0.0995 0.022 Uiso 1 1 calc R . .
C22 C 0.7594(5) 0.4463(4) 0.06463(11) 0.0185(4) Uani 1 1 d . . .
H22A H 0.8687 0.5343 0.0986 0.022 Uiso 1 1 calc R . .
H22B H 0.6244 0.5716 0.0526 0.022 Uiso 1 1 calc R . .
C23 C 0.9343(5) 0.3786(4) 0.01166(11) 0.0181(4) Uani 1 1 d . . .
H23A H 1.0730 0.2584 0.0243 0.022 Uiso 1 1 calc R . .
H23B H 0.8259 0.2837 -0.0215 0.022 Uiso 1 1 calc R . .
C31 C 0.4520(6) 1.0743(5) 0.47341(12) 0.0237(5) Uani 1 1 d . . .
I1 I 0.28525(3) 0.81898(3) 0.398907(7) 0.02466(6) Uani 1 1 d . . .
F31B F 0.6564(4) 1.2167(4) 0.45467(8) 0.0353(4) Uani 1 1 d . . .
F31A F 0.2676(4) 1.2435(4) 0.49308(9) 0.0345(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
N11 C12 1.334(3) . ?
N11 C16 1.338(4) . ?
N11 I1 2.930(3) . ?
C12 C13 1.393(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.389(3) . ?
C13 C17 1.501(3) . ?
C14 C15 1.383(4) . ?
C14 H14 0.9500 . ?
C15 C16 1.377(4) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 O17 1.232(3) . ?
C17 N17 1.343(3) . ?
N17 C21 1.457(3) . ?
N17 H17 0.8800 . ?
C21 C22 1.515(3) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 C23 1.521(3) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 C23 1.520(4) 2_765 ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C31 F31B 1.343(3) . ?
C31 F31A 1.346(3) . ?
C31 C31 1.524(5) 2_676 ?
C31 I1 2.155(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 N11 C16 117.2(2) . . ?
C12 N11 I1 122.14(18) . . ?
C16 N11 I1 116.79(18) . . ?
N11 C12 C13 123.3(2) . . ?
N11 C12 H12 118.3 . . ?
C13 C12 H12 118.3 . . ?
C14 C13 C12 118.2(2) . . ?
C14 C13 C17 118.9(2) . . ?
C12 C13 C17 122.8(2) . . ?
C15 C14 C13 118.8(2) . . ?
C15 C14 H14 120.6 . . ?
C13 C14 H14 120.6 . . ?
C16 C15 C14 118.5(2) . . ?
C16 C15 H15 120.7 . . ?
C14 C15 H15 120.7 . . ?
N11 C16 C15 123.9(2) . . ?
N11 C16 H16 118.1 . . ?
C15 C16 H16 118.1 . . ?
O17 C17 N17 122.3(2) . . ?
O17 C17 C13 121.0(2) . . ?
N17 C17 C13 116.7(2) . . ?
C17 N17 C21 119.9(2) . . ?
C17 N17 H17 120.1 . . ?
C21 N17 H17 120.1 . . ?
N17 C21 C22 111.27(19) . . ?
N17 C21 H21A 109.4 . . ?
C22 C21 H21A 109.4 . . ?
N17 C21 H21B 109.4 . . ?
C22 C21 H21B 109.4 . . ?
H21A C21 H21B 108.0 . . ?
C21 C22 C23 111.67(19) . . ?
C21 C22 H22A 109.3 . . ?
C23 C22 H22A 109.3 . . ?
C21 C22 H22B 109.3 . . ?
C23 C22 H22B 109.3 . . ?
H22A C22 H22B 107.9 . . ?
C23 C23 C22 112.8(2) 2_765 . ?
C23 C23 H23A 109.0 2_765 . ?
C22 C23 H23A 109.0 . . ?
C23 C23 H23B 109.0 2_765 . ?
C22 C23 H23B 109.0 . . ?
H23A C23 H23B 107.8 . . ?
F31B C31 F31A 108.0(2) . . ?
F31B C31 C31 108.6(3) . 2_676 ?
F31A C31 C31 108.1(3) . 2_676 ?
F31B C31 I1 109.56(17) . . ?
F31A C31 I1 109.08(18) . . ?
C31 C31 I1 113.4(2) 2_676 . ?
C31 I1 N11 178.83(9) . . ?

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 -0.4(4) . . . . ?
I1 N11 C12 C13 156.69(18) . . . . ?
N11 C12 C13 C14 -0.2(4) . . . . ?
N11 C12 C13 C17 -175.8(2) . . . . ?
C12 C13 C14 C15 1.1(4) . . . . ?
C17 C13 C14 C15 176.8(2) . . . . ?
C13 C14 C15 C16 -1.4(4) . . . . ?
C12 N11 C16 C15 0.1(4) . . . . ?
I1 N11 C16 C15 -158.2(2) . . . . ?
C14 C15 C16 N11 0.8(4) . . . . ?
C14 C13 C17 O17 -25.6(3) . . . . ?
C12 C13 C17 O17 150.0(2) . . . . ?
C14 C13 C17 N17 155.1(2) . . . . ?
C12 C13 C17 N17 -29.3(3) . . . . ?
O17 C17 N17 C21 -2.1(4) . . . . ?
C13 C17 N17 C21 177.1(2) . . . . ?
C17 N17 C21 C22 -175.9(2) . . . . ?
N17 C21 C22 C23 -177.13(19) . . . . ?
C21 C22 C23 C23 177.8(2) . . . 2_765 ?

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
N17 H17 O17 0.88 2.11 2.958(3) 161.8 1_565

_diffrn_measured_fraction_theta_max 0.873
_diffrn_reflns_theta_full        27.50
_diffrn_measured_fraction_theta_full 0.968
_refine_diff_density_max         1.062
_refine_diff_density_min         -0.634
_refine_diff_density_rms         0.132
_database_code_depnum_ccdc_archive 'CCDC 1011550'
#######################################################################
#
#                 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_A6D6

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
DW-8-9 (3-pyridyl)-CONH-(CH2)6-NHCO-(3-pyridyl), I-(CF2)6-I
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         
;
(C18 H22 N4 O2) (C6 F12 I2)
;
_chemical_formula_sum            'C24 H22 F12 I2 N4 O2'
_chemical_formula_weight         880.26

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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   Pca2(1)

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

_cell_length_a                   64.445(6)
_cell_length_b                   4.9349(4)
_cell_length_c                   9.1473(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2909.1(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    9890
_cell_measurement_theta_min      2.31
_cell_measurement_theta_max      31.18

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.06
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.010
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1696
_exptl_absorpt_coefficient_mu    2.270
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6598
_exptl_absorpt_correction_T_max  0.7463
_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            24753
_diffrn_reflns_av_R_equivalents  0.0362
_diffrn_reflns_av_sigmaI/netI    0.0450
_diffrn_reflns_limit_h_min       -86
_diffrn_reflns_limit_h_max       85
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         1.90
_diffrn_reflns_theta_max         32.03
_reflns_number_total             8238
_reflns_number_gt                6834
_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)+(0.0700P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         8238
_refine_ls_number_parameters     398
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0496
_refine_ls_R_factor_gt           0.0367
_refine_ls_wR_factor_ref         0.1164
_refine_ls_wR_factor_gt          0.1060
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.047
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N11 N 0.26067(7) 0.6603(11) 0.5358(6) 0.0395(12) Uani 1 1 d . . .
C12 C 0.24302(9) 0.7313(13) 0.5976(7) 0.0359(13) Uani 1 1 d . . .
H12 H 0.2432 0.8824 0.6619 0.043 Uiso 1 1 calc R . .
C13 C 0.22431(7) 0.6022(10) 0.5756(5) 0.0220(9) Uani 1 1 d . . .
C14 C 0.22387(8) 0.3948(12) 0.4777(6) 0.0345(12) Uani 1 1 d . . .
H14 H 0.2113 0.3025 0.4569 0.041 Uiso 1 1 calc R . .
C15 C 0.24223(11) 0.3207(14) 0.4088(8) 0.0457(17) Uani 1 1 d . . .
H15 H 0.2423 0.1788 0.3386 0.055 Uiso 1 1 calc R . .
C16 C 0.26022(9) 0.4528(14) 0.4423(6) 0.0377(14) Uani 1 1 d . . .
H16 H 0.2728 0.3953 0.3977 0.045 Uiso 1 1 calc R . .
C17 C 0.20547(7) 0.6978(10) 0.6579(7) 0.0246(9) Uani 1 1 d . . .
N17 N 0.19227(6) 0.5054(8) 0.6972(5) 0.0258(9) Uani 1 1 d . . .
H17 H 0.1954 0.3362 0.6762 0.031 Uiso 1 1 calc R . .
O17 O 0.20349(6) 0.9401(9) 0.6872(5) 0.0378(11) Uani 1 1 d . . .
N21 N -0.00901(7) 0.1496(9) 0.9551(5) 0.0266(9) Uani 1 1 d . . .
C22 C 0.00857(7) 0.0997(10) 0.8832(5) 0.0214(9) Uani 1 1 d . . .
H22 H 0.0087 -0.0486 0.8170 0.026 Uiso 1 1 calc R . .
C23 C 0.02663(7) 0.2497(10) 0.8986(5) 0.0200(9) Uani 1 1 d . . .
C24 C 0.02656(8) 0.4615(10) 0.9972(6) 0.0253(10) Uani 1 1 d . . .
H24 H 0.0386 0.5700 1.0111 0.030 Uiso 1 1 calc R . .
C25 C 0.00856(9) 0.5123(11) 1.0755(6) 0.0286(12) Uani 1 1 d . . .
H25 H 0.0082 0.6532 1.1462 0.034 Uiso 1 1 calc R . .
C26 C -0.00878(8) 0.3571(11) 1.0500(6) 0.0302(11) Uani 1 1 d . . .
H26 H -0.0212 0.3986 1.1018 0.036 Uiso 1 1 calc R . .
C27 C 0.04510(7) 0.1745(9) 0.8100(6) 0.0200(8) Uani 1 1 d . . .
N27 N 0.05737(6) 0.3781(8) 0.7691(4) 0.0213(8) Uani 1 1 d . . .
H27 H 0.0537 0.5436 0.7937 0.026 Uiso 1 1 calc R . .
O27 O 0.04785(5) -0.0635(7) 0.7716(4) 0.0261(8) Uani 1 1 d . . .
C31 C 0.17285(8) 0.5585(12) 0.7735(6) 0.0311(11) Uani 1 1 d . . .
H31A H 0.1713 0.7564 0.7876 0.037 Uiso 1 1 calc R . .
H31B H 0.1733 0.4728 0.8713 0.037 Uiso 1 1 calc R . .
C32 C 0.15441(7) 0.4518(11) 0.6910(5) 0.0257(10) Uani 1 1 d . . .
H32A H 0.1560 0.2538 0.6775 0.031 Uiso 1 1 calc R . .
H32B H 0.1540 0.5366 0.5930 0.031 Uiso 1 1 calc R . .
C33 C 0.13401(8) 0.5086(12) 0.7701(6) 0.0314(12) Uani 1 1 d . . .
H33A H 0.1345 0.4233 0.8680 0.038 Uiso 1 1 calc R . .
H33B H 0.1326 0.7066 0.7842 0.038 Uiso 1 1 calc R . .
C34 C 0.11522(7) 0.4045(12) 0.6889(5) 0.0293(11) Uani 1 1 d . . .
H34A H 0.1170 0.2079 0.6711 0.035 Uiso 1 1 calc R . .
H34B H 0.1145 0.4955 0.5927 0.035 Uiso 1 1 calc R . .
C35 C 0.09490(8) 0.4497(12) 0.7696(6) 0.0292(11) Uani 1 1 d . . .
H35A H 0.0956 0.3580 0.8658 0.035 Uiso 1 1 calc R . .
H35B H 0.0931 0.6461 0.7875 0.035 Uiso 1 1 calc R . .
C36 C 0.07648(7) 0.3448(10) 0.6864(5) 0.0238(10) Uani 1 1 d . . .
H36A H 0.0753 0.4434 0.5925 0.029 Uiso 1 1 calc R . .
H36B H 0.0786 0.1504 0.6643 0.029 Uiso 1 1 calc R . .
C41 C 0.32484(8) 0.9874(10) 0.7695(6) 0.0267(11) Uani 1 1 d . . .
I1 I 0.297784(4) 0.85611(7) 0.65099(4) 0.03197(9) Uani 1 1 d . . .
F41A F 0.32331(5) 1.2498(6) 0.8021(4) 0.0404(8) Uani 1 1 d . . .
F41B F 0.32583(5) 0.8530(8) 0.8968(4) 0.0377(8) Uani 1 1 d . . .
C42 C 0.34517(7) 0.9359(9) 0.6866(5) 0.0209(9) Uani 1 1 d . . .
F42A F 0.34527(5) 1.0955(6) 0.5672(3) 0.0295(6) Uani 1 1 d . . .
F42B F 0.34566(4) 0.6787(5) 0.6424(4) 0.0282(6) Uani 1 1 d . . .
C43 C 0.36532(8) 0.9952(9) 0.7751(5) 0.0196(9) Uani 1 1 d . . .
F43A F 0.36322(5) 1.2306(6) 0.8457(3) 0.0324(7) Uani 1 1 d . . .
F43B F 0.36733(5) 0.7968(7) 0.8748(3) 0.0304(7) Uani 1 1 d . . .
C44 C 0.38536(7) 1.0069(9) 0.6815(5) 0.0207(9) Uani 1 1 d . . .
F44A F 0.38537(5) 1.2476(6) 0.6127(3) 0.0321(7) Uani 1 1 d . . .
F44B F 0.38491(5) 0.8121(7) 0.5809(3) 0.0328(7) Uani 1 1 d . . .
C45 C 0.40561(8) 0.9806(9) 0.7713(5) 0.0213(9) Uani 1 1 d . . .
F45A F 0.40415(5) 1.1490(7) 0.8859(3) 0.0282(7) Uani 1 1 d . . .
F45B F 0.40693(4) 0.7267(5) 0.8201(4) 0.0284(6) Uani 1 1 d . . .
C46 C 0.42577(8) 1.0486(10) 0.6901(5) 0.0231(9) Uani 1 1 d . . .
I2 I 0.452944(4) 0.97912(6) 0.82126(4) 0.02616(9) Uani 1 1 d . . .
F46A F 0.42538(4) 1.3074(6) 0.6451(4) 0.0332(6) Uani 1 1 d . . .
F46B F 0.42663(5) 0.8954(7) 0.5675(3) 0.0315(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 1.317(7) . ?
N11 C16 1.335(8) . ?
N11 I1 2.786(5) . ?
C12 C13 1.379(7) . ?
C12 H12 0.9500 . ?
C13 C14 1.360(7) . ?
C13 C17 1.505(7) . ?
C14 C15 1.390(8) . ?
C14 H14 0.9500 . ?
C15 C16 1.365(9) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 O17 1.232(6) . ?
C17 N17 1.324(6) . ?
N17 C31 1.457(6) . ?
N17 H17 0.8800 . ?
N21 C22 1.333(6) . ?
N21 C26 1.343(7) . ?
C22 C23 1.386(7) . ?
C22 H22 0.9500 . ?
C23 C24 1.381(7) . ?
C23 C27 1.487(6) . ?
C24 C25 1.386(7) . ?
C24 H24 0.9500 . ?
C25 C26 1.375(8) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?
C27 O27 1.239(5) . ?
C27 N27 1.333(6) . ?
N27 C36 1.454(6) . ?
N27 H27 0.8800 . ?
C31 C32 1.503(7) . ?
C31 H31A 0.9900 . ?
C31 H31B 0.9900 . ?
C32 C33 1.527(7) . ?
C32 H32A 0.9900 . ?
C32 H32B 0.9900 . ?
C33 C34 1.511(7) . ?
C33 H33A 0.9900 . ?
C33 H33B 0.9900 . ?
C34 C35 1.519(7) . ?
C34 H34A 0.9900 . ?
C34 H34B 0.9900 . ?
C35 C36 1.502(7) . ?
C35 H35A 0.9900 . ?
C35 H35B 0.9900 . ?
C36 H36A 0.9900 . ?
C36 H36B 0.9900 . ?
C41 F41A 1.332(6) . ?
C41 F41B 1.342(6) . ?
C41 C42 1.535(7) . ?
C41 I1 2.153(5) . ?
C42 F42B 1.333(5) . ?
C42 F42A 1.347(5) . ?
C42 C43 1.557(7) . ?
C43 F43A 1.336(5) . ?
C43 F43B 1.344(5) . ?
C43 C44 1.551(6) . ?
C44 F44B 1.331(5) . ?
C44 F44A 1.344(5) . ?
C44 C45 1.547(7) . ?
C45 F45B 1.333(5) . ?
C45 F45A 1.341(5) . ?
C45 C46 1.534(7) . ?
C46 F46A 1.342(6) . ?
C46 F46B 1.354(5) . ?
C46 I2 2.150(5) . ?
I2 N21 2.813(4) 3_565 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C12 N11 C16 117.4(5) . . ?
C12 N11 I1 119.1(4) . . ?
C16 N11 I1 121.8(4) . . ?
N11 C12 C13 124.7(5) . . ?
N11 C12 H12 117.6 . . ?
C13 C12 H12 117.6 . . ?
C14 C13 C12 117.5(5) . . ?
C14 C13 C17 123.2(5) . . ?
C12 C13 C17 119.2(4) . . ?
C13 C14 C15 118.6(5) . . ?
C13 C14 H14 120.7 . . ?
C15 C14 H14 120.7 . . ?
C16 C15 C14 119.7(6) . . ?
C16 C15 H15 120.1 . . ?
C14 C15 H15 120.1 . . ?
N11 C16 C15 121.9(6) . . ?
N11 C16 H16 119.0 . . ?
C15 C16 H16 119.0 . . ?
O17 C17 N17 124.8(5) . . ?
O17 C17 C13 119.7(5) . . ?
N17 C17 C13 115.4(4) . . ?
C17 N17 C31 123.5(4) . . ?
C17 N17 H17 118.2 . . ?
C31 N17 H17 118.2 . . ?
C22 N21 C26 116.8(4) . . ?
N21 C22 C23 124.4(5) . . ?
N21 C22 H22 117.8 . . ?
C23 C22 H22 117.8 . . ?
C24 C23 C22 117.9(4) . . ?
C24 C23 C27 123.2(4) . . ?
C22 C23 C27 118.9(4) . . ?
C23 C24 C25 118.5(5) . . ?
C23 C24 H24 120.8 . . ?
C25 C24 H24 120.8 . . ?
C26 C25 C24 119.5(5) . . ?
C26 C25 H25 120.3 . . ?
C24 C25 H25 120.3 . . ?
N21 C26 C25 122.9(5) . . ?
N21 C26 H26 118.5 . . ?
C25 C26 H26 118.5 . . ?
O27 C27 N27 123.4(5) . . ?
O27 C27 C23 120.4(4) . . ?
N27 C27 C23 116.1(4) . . ?
C27 N27 C36 124.3(4) . . ?
C27 N27 H27 117.9 . . ?
C36 N27 H27 117.9 . . ?
N17 C31 C32 112.0(4) . . ?
N17 C31 H31A 109.2 . . ?
C32 C31 H31A 109.2 . . ?
N17 C31 H31B 109.2 . . ?
C32 C31 H31B 109.2 . . ?
H31A C31 H31B 107.9 . . ?
C31 C32 C33 112.2(4) . . ?
C31 C32 H32A 109.2 . . ?
C33 C32 H32A 109.2 . . ?
C31 C32 H32B 109.2 . . ?
C33 C32 H32B 109.2 . . ?
H32A C32 H32B 107.9 . . ?
C34 C33 C32 113.3(4) . . ?
C34 C33 H33A 108.9 . . ?
C32 C33 H33A 108.9 . . ?
C34 C33 H33B 108.9 . . ?
C32 C33 H33B 108.9 . . ?
H33A C33 H33B 107.7 . . ?
C33 C34 C35 113.7(4) . . ?
C33 C34 H34A 108.8 . . ?
C35 C34 H34A 108.8 . . ?
C33 C34 H34B 108.8 . . ?
C35 C34 H34B 108.8 . . ?
H34A C34 H34B 107.7 . . ?
C36 C35 C34 112.6(4) . . ?
C36 C35 H35A 109.1 . . ?
C34 C35 H35A 109.1 . . ?
C36 C35 H35B 109.1 . . ?
C34 C35 H35B 109.1 . . ?
H35A C35 H35B 107.8 . . ?
N27 C36 C35 111.5(4) . . ?
N27 C36 H36A 109.3 . . ?
C35 C36 H36A 109.3 . . ?
N27 C36 H36B 109.3 . . ?
C35 C36 H36B 109.3 . . ?
H36A C36 H36B 108.0 . . ?
F41A C41 F41B 106.9(4) . . ?
F41A C41 C42 109.6(4) . . ?
F41B C41 C42 107.8(4) . . ?
F41A C41 I1 110.2(3) . . ?
F41B C41 I1 109.1(3) . . ?
C42 C41 I1 113.1(3) . . ?
C41 I1 N11 171.84(18) . . ?
F42B C42 F42A 108.1(4) . . ?
F42B C42 C41 109.2(4) . . ?
F42A C42 C41 107.9(4) . . ?
F42B C42 C43 108.5(4) . . ?
F42A C42 C43 107.9(4) . . ?
C41 C42 C43 115.1(4) . . ?
F43A C43 F43B 108.3(4) . . ?
F43A C43 C44 108.6(4) . . ?
F43B C43 C44 108.7(4) . . ?
F43A C43 C42 109.3(4) . . ?
F43B C43 C42 107.2(4) . . ?
C44 C43 C42 114.5(4) . . ?
F44B C44 F44A 108.3(4) . . ?
F44B C44 C45 109.0(4) . . ?
F44A C44 C45 108.8(4) . . ?
F44B C44 C43 109.6(4) . . ?
F44A C44 C43 107.0(4) . . ?
C45 C44 C43 114.0(4) . . ?
F45B C45 F45A 109.0(4) . . ?
F45B C45 C46 108.3(4) . . ?
F45A C45 C46 107.6(4) . . ?
F45B C45 C44 108.1(4) . . ?
F45A C45 C44 107.7(4) . . ?
C46 C45 C44 116.0(4) . . ?
F46A C46 F46B 106.1(4) . . ?
F46A C46 C45 109.9(4) . . ?
F46B C46 C45 108.3(4) . . ?
F46A C46 I2 109.8(3) . . ?
F46B C46 I2 109.9(3) . . ?
C45 C46 I2 112.6(3) . . ?
C46 I2 N21 171.36(16) . 3_565 ?

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 1.9(9) . . . . ?
I1 N11 C12 C13 -163.7(4) . . . . ?
N11 C12 C13 C14 -3.3(9) . . . . ?
N11 C12 C13 C17 177.6(5) . . . . ?
C12 C13 C14 C15 1.6(9) . . . . ?
C17 C13 C14 C15 -179.3(6) . . . . ?
C13 C14 C15 C16 1.2(10) . . . . ?
C12 N11 C16 C15 1.2(9) . . . . ?
I1 N11 C16 C15 166.4(5) . . . . ?
C14 C15 C16 N11 -2.7(11) . . . . ?
C14 C13 C17 O17 -145.7(6) . . . . ?
C12 C13 C17 O17 33.4(8) . . . . ?
C14 C13 C17 N17 36.2(8) . . . . ?
C12 C13 C17 N17 -144.7(5) . . . . ?
O17 C17 N17 C31 4.0(9) . . . . ?
C13 C17 N17 C31 -178.0(4) . . . . ?
C26 N21 C22 C23 -1.1(7) . . . . ?
N21 C22 C23 C24 1.4(7) . . . . ?
N21 C22 C23 C27 -179.1(5) . . . . ?
C22 C23 C24 C25 0.2(7) . . . . ?
C27 C23 C24 C25 -179.2(5) . . . . ?
C23 C24 C25 C26 -1.9(8) . . . . ?
C22 N21 C26 C25 -0.8(7) . . . . ?
C24 C25 C26 N21 2.3(8) . . . . ?
C24 C23 C27 O27 150.2(5) . . . . ?
C22 C23 C27 O27 -29.2(7) . . . . ?
C24 C23 C27 N27 -33.5(7) . . . . ?
C22 C23 C27 N27 147.1(5) . . . . ?
O27 C27 N27 C36 -6.0(8) . . . . ?
C23 C27 N27 C36 177.9(4) . . . . ?
C17 N17 C31 C32 122.5(6) . . . . ?
N17 C31 C32 C33 -179.6(5) . . . . ?
C31 C32 C33 C34 179.7(5) . . . . ?
C32 C33 C34 C35 177.6(5) . . . . ?
C33 C34 C35 C36 179.9(5) . . . . ?
C27 N27 C36 C35 -119.6(5) . . . . ?
C34 C35 C36 N27 177.1(4) . . . . ?
F41A C41 C42 F42B -174.2(4) . . . . ?
F41B C41 C42 F42B 69.9(5) . . . . ?
I1 C41 C42 F42B -50.8(5) . . . . ?
F41A C41 C42 F42A -56.9(5) . . . . ?
F41B C41 C42 F42A -172.9(4) . . . . ?
I1 C41 C42 F42A 66.5(4) . . . . ?
F41A C41 C42 C43 63.6(6) . . . . ?
F41B C41 C42 C43 -52.3(5) . . . . ?
I1 C41 C42 C43 -173.0(3) . . . . ?
F42B C42 C43 F43A -167.1(4) . . . . ?
F42A C42 C43 F43A 76.0(5) . . . . ?
C41 C42 C43 F43A -44.5(5) . . . . ?
F42B C42 C43 F43B -49.9(5) . . . . ?
F42A C42 C43 F43B -166.7(4) . . . . ?
C41 C42 C43 F43B 72.7(5) . . . . ?
F42B C42 C43 C44 70.8(5) . . . . ?
F42A C42 C43 C44 -46.0(5) . . . . ?
C41 C42 C43 C44 -166.6(4) . . . . ?
F43A C43 C44 F44B -162.8(4) . . . . ?
F43B C43 C44 F44B 79.5(4) . . . . ?
C42 C43 C44 F44B -40.4(5) . . . . ?
F43A C43 C44 F44A -45.6(5) . . . . ?
F43B C43 C44 F44A -163.2(4) . . . . ?
C42 C43 C44 F44A 76.9(5) . . . . ?
F43A C43 C44 C45 74.7(5) . . . . ?
F43B C43 C44 C45 -43.0(5) . . . . ?
C42 C43 C44 C45 -162.9(4) . . . . ?
F44B C44 C45 F45B -52.5(5) . . . . ?
F44A C44 C45 F45B -170.4(4) . . . . ?
C43 C44 C45 F45B 70.3(5) . . . . ?
F44B C44 C45 F45A -170.1(4) . . . . ?
F44A C44 C45 F45A 71.9(5) . . . . ?
C43 C44 C45 F45A -47.3(5) . . . . ?
F44B C44 C45 C46 69.3(5) . . . . ?
F44A C44 C45 C46 -48.7(5) . . . . ?
C43 C44 C45 C46 -167.9(4) . . . . ?
F45B C45 C46 F46A -177.2(4) . . . . ?
F45A C45 C46 F46A -59.6(5) . . . . ?
C44 C45 C46 F46A 61.1(5) . . . . ?
F45B C45 C46 F46B 67.3(5) . . . . ?
F45A C45 C46 F46B -175.1(3) . . . . ?
C44 C45 C46 F46B -54.4(5) . . . . ?
F45B C45 C46 I2 -54.5(4) . . . . ?
F45A C45 C46 I2 63.2(4) . . . . ?
C44 C45 C46 I2 -176.1(3) . . . . ?

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
N17 H17 O17 0.88 2.03 2.883(6) 164.5 1_545
N27 H27 O27 0.88 1.98 2.823(5) 158.6 1_565

_diffrn_measured_fraction_theta_max 0.899
_diffrn_reflns_theta_full        30.00
_diffrn_measured_fraction_theta_full 0.962
_refine_diff_density_max         0.642
_refine_diff_density_min         -0.840
_refine_diff_density_rms         0.113
_database_code_depnum_ccdc_archive 'CCDC 1011551'
#######################################################################
#
#                 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_A6D8

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
DW-8-18 (3-pyridyl)-CONH-(CH2)6-NHCO-(3-pyridyl), I-(CF2)8-I
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         
;
(C18 H22 N4 O2) (C8 F16 I2)
;
_chemical_formula_sum            'C26 H22 F16 I2 N4 O2'
_chemical_formula_weight         980.28

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

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

_cell_length_a                   5.0528(4)
_cell_length_b                   5.1104(4)
_cell_length_c                   29.870(2)
_cell_angle_alpha                86.386(2)
_cell_angle_beta                 87.930(2)
_cell_angle_gamma                87.776(2)
_cell_volume                     768.75(10)
_cell_formula_units_Z            1
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    9035
_cell_measurement_theta_min      3.42
_cell_measurement_theta_max      31.34

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.06
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.117
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             472
_exptl_absorpt_coefficient_mu    2.178
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5425
_exptl_absorpt_correction_T_max  0.8804
_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            13832
_diffrn_reflns_av_R_equivalents  0.0323
_diffrn_reflns_av_sigmaI/netI    0.0351
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -43
_diffrn_reflns_limit_l_max       43
_diffrn_reflns_theta_min         2.05
_diffrn_reflns_theta_max         31.43
_reflns_number_total             4733
_reflns_number_gt                4368
_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)+(0.0500P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4733
_refine_ls_number_parameters     229
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0301
_refine_ls_R_factor_gt           0.0273
_refine_ls_wR_factor_ref         0.0729
_refine_ls_wR_factor_gt          0.0710
_refine_ls_goodness_of_fit_ref   0.975
_refine_ls_restrained_S_all      0.975
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N11 N -0.0316(4) 0.5733(4) 0.22186(7) 0.0233(4) Uani 1 1 d . . .
C12 C 0.1226(4) 0.6390(4) 0.18592(7) 0.0199(4) Uani 1 1 d . . .
H12 H 0.2687 0.5245 0.1789 0.024 Uiso 1 1 calc R . .
C13 C 0.0817(4) 0.8653(4) 0.15826(7) 0.0163(3) Uani 1 1 d . . .
C14 C -0.1340(4) 1.0316(4) 0.16868(7) 0.0196(4) Uani 1 1 d . . .
H14 H -0.1685 1.1886 0.1508 0.023 Uiso 1 1 calc R . .
C15 C -0.2973(4) 0.9645(5) 0.20559(8) 0.0236(4) Uani 1 1 d . . .
H15 H -0.4467 1.0734 0.2132 0.028 Uiso 1 1 calc R . .
C16 C -0.2382(4) 0.7356(4) 0.23114(8) 0.0235(4) Uani 1 1 d . . .
H16 H -0.3499 0.6914 0.2565 0.028 Uiso 1 1 calc R . .
C17 C 0.2670(4) 0.9421(4) 0.12005(7) 0.0161(3) Uani 1 1 d . . .
N17 N 0.4030(3) 0.7496(3) 0.09990(6) 0.0178(3) Uani 1 1 d . . .
H17 H 0.363(5) 0.602(6) 0.1052(10) 0.021 Uiso 1 1 d . . .
O17 O 0.2940(3) 1.1766(3) 0.10801(5) 0.0218(3) Uani 1 1 d . . .
C21 C 0.5959(4) 0.8103(4) 0.06371(7) 0.0174(4) Uani 1 1 d . . .
H21A H 0.7269 0.9300 0.0742 0.021 Uiso 1 1 calc R . .
H21B H 0.5046 0.9014 0.0381 0.021 Uiso 1 1 calc R . .
C22 C 0.7388(4) 0.5634(4) 0.04833(7) 0.0181(4) Uani 1 1 d . . .
H22A H 0.6068 0.4396 0.0396 0.022 Uiso 1 1 calc R . .
H22B H 0.8381 0.4777 0.0736 0.022 Uiso 1 1 calc R . .
C23 C 0.9308(4) 0.6230(4) 0.00864(7) 0.0172(4) Uani 1 1 d . . .
H23A H 0.8322 0.7155 -0.0160 0.021 Uiso 1 1 calc R . .
H23B H 1.0662 0.7418 0.0179 0.021 Uiso 1 1 calc R . .
C31 C 0.2840(4) -0.0387(4) 0.35203(7) 0.0194(4) Uani 1 1 d . . .
I1 I 0.14994(2) 0.21997(2) 0.296602(4) 0.01955(6) Uani 1 1 d . . .
F31A F 0.1018(3) -0.2205(3) 0.36145(5) 0.0265(3) Uani 1 1 d . . .
F31B F 0.5118(3) -0.1637(3) 0.33972(5) 0.0286(3) Uani 1 1 d . . .
C32 C 0.3275(4) 0.1113(4) 0.39448(7) 0.0171(4) Uani 1 1 d . . .
F32A F 0.0974(2) 0.2380(2) 0.40497(4) 0.0229(3) Uani 1 1 d . . .
F32B F 0.5119(3) 0.2905(2) 0.38388(5) 0.0246(3) Uani 1 1 d . . .
C33 C 0.4181(4) -0.0634(4) 0.43622(7) 0.0172(4) Uani 1 1 d . . .
F33A F 0.2371(3) -0.2461(2) 0.44548(4) 0.0235(3) Uani 1 1 d . . .
F33B F 0.6514(2) -0.1824(3) 0.42524(4) 0.0246(3) Uani 1 1 d . . .
C34 C 0.4534(4) 0.0879(4) 0.47931(7) 0.0171(4) Uani 1 1 d . . .
F34A F 0.2196(3) 0.2058(3) 0.49015(4) 0.0241(3) Uani 1 1 d . . .
F34B F 0.6324(3) 0.2733(2) 0.46989(4) 0.0242(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 1.337(3) . ?
N11 C16 1.340(3) . ?
N11 I1 2.9322(19) . ?
C12 C13 1.391(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.394(3) . ?
C13 C17 1.493(3) . ?
C14 C15 1.387(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.384(3) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 O17 1.241(2) . ?
C17 N17 1.340(2) . ?
N17 C21 1.456(3) . ?
N17 H17 0.79(3) . ?
C21 C22 1.517(3) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 C23 1.528(3) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 C23 1.524(4) 2_765 ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C31 F31A 1.343(2) . ?
C31 F31B 1.345(2) . ?
C31 C32 1.549(3) . ?
C31 I1 2.164(2) . ?
C32 F32A 1.346(2) . ?
C32 F32B 1.347(2) . ?
C32 C33 1.559(3) . ?
C33 F33A 1.341(2) . ?
C33 F33B 1.345(2) . ?
C33 C34 1.562(3) . ?
C34 F34A 1.344(2) . ?
C34 F34B 1.345(2) . ?
C34 C34 1.558(4) 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 C16 117.37(19) . . ?
C12 N11 I1 122.98(14) . . ?
C16 N11 I1 116.02(14) . . ?
N11 C12 C13 123.81(19) . . ?
N11 C12 H12 118.1 . . ?
C13 C12 H12 118.1 . . ?
C12 C13 C14 117.79(18) . . ?
C12 C13 C17 122.59(17) . . ?
C14 C13 C17 119.52(18) . . ?
C15 C14 C13 119.0(2) . . ?
C15 C14 H14 120.5 . . ?
C13 C14 H14 120.5 . . ?
C16 C15 C14 118.7(2) . . ?
C16 C15 H15 120.7 . . ?
C14 C15 H15 120.7 . . ?
N11 C16 C15 123.3(2) . . ?
N11 C16 H16 118.3 . . ?
C15 C16 H16 118.3 . . ?
O17 C17 N17 121.85(18) . . ?
O17 C17 C13 120.55(17) . . ?
N17 C17 C13 117.60(17) . . ?
C17 N17 C21 120.64(16) . . ?
C17 N17 H17 119(2) . . ?
C21 N17 H17 119(2) . . ?
N17 C21 C22 111.31(16) . . ?
N17 C21 H21A 109.4 . . ?
C22 C21 H21A 109.4 . . ?
N17 C21 H21B 109.4 . . ?
C22 C21 H21B 109.4 . . ?
H21A C21 H21B 108.0 . . ?
C21 C22 C23 111.79(16) . . ?
C21 C22 H22A 109.3 . . ?
C23 C22 H22A 109.3 . . ?
C21 C22 H22B 109.3 . . ?
C23 C22 H22B 109.3 . . ?
H22A C22 H22B 107.9 . . ?
C23 C23 C22 112.9(2) 2_765 . ?
C23 C23 H23A 109.0 2_765 . ?
C22 C23 H23A 109.0 . . ?
C23 C23 H23B 109.0 2_765 . ?
C22 C23 H23B 109.0 . . ?
H23A C23 H23B 107.8 . . ?
F31A C31 F31B 107.86(16) . . ?
F31A C31 C32 109.48(17) . . ?
F31B C31 C32 109.41(16) . . ?
F31A C31 I1 108.55(13) . . ?
F31B C31 I1 109.32(14) . . ?
C32 C31 I1 112.12(13) . . ?
C31 I1 N11 179.64(6) . . ?
F32A C32 F32B 108.59(15) . . ?
F32A C32 C31 107.45(16) . . ?
F32B C32 C31 107.84(16) . . ?
F32A C32 C33 108.98(16) . . ?
F32B C32 C33 108.75(16) . . ?
C31 C32 C33 115.07(16) . . ?
F33A C33 F33B 109.12(16) . . ?
F33A C33 C32 108.09(16) . . ?
F33B C33 C32 107.78(16) . . ?
F33A C33 C34 108.52(16) . . ?
F33B C33 C34 108.42(16) . . ?
C32 C33 C34 114.80(16) . . ?
F34A C34 F34B 108.72(15) . . ?
F34A C34 C34 108.5(2) . 2_656 ?
F34B C34 C34 108.4(2) . 2_656 ?
F34A C34 C33 108.12(16) . . ?
F34B C34 C33 108.56(16) . . ?
C34 C34 C33 114.41(19) 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
C16 N11 C12 C13 0.6(3) . . . . ?
I1 N11 C12 C13 -157.04(16) . . . . ?
N11 C12 C13 C14 -0.4(3) . . . . ?
N11 C12 C13 C17 176.0(2) . . . . ?
C12 C13 C14 C15 -0.3(3) . . . . ?
C17 C13 C14 C15 -176.84(19) . . . . ?
C13 C14 C15 C16 0.8(3) . . . . ?
C12 N11 C16 C15 -0.1(3) . . . . ?
I1 N11 C16 C15 159.07(18) . . . . ?
C14 C15 C16 N11 -0.5(3) . . . . ?
C12 C13 C17 O17 -150.4(2) . . . . ?
C14 C13 C17 O17 26.0(3) . . . . ?
C12 C13 C17 N17 29.0(3) . . . . ?
C14 C13 C17 N17 -154.7(2) . . . . ?
O17 C17 N17 C21 2.1(3) . . . . ?
C13 C17 N17 C21 -177.26(18) . . . . ?
C17 N17 C21 C22 175.97(19) . . . . ?
N17 C21 C22 C23 176.83(17) . . . . ?
C21 C22 C23 C23 -177.8(2) . . . 2_765 ?
F31A C31 I1 N11 120(11) . . . . ?
F31B C31 I1 N11 -122(11) . . . . ?
C32 C31 I1 N11 -1(11) . . . . ?
C12 N11 I1 C31 108(11) . . . . ?
C16 N11 I1 C31 -50(11) . . . . ?
F31A C31 C32 F32A -63.4(2) . . . . ?
F31B C31 C32 F32A 178.56(15) . . . . ?
I1 C31 C32 F32A 57.09(18) . . . . ?
F31A C31 C32 F32B 179.68(15) . . . . ?
F31B C31 C32 F32B 61.7(2) . . . . ?
I1 C31 C32 F32B -59.79(17) . . . . ?
F31A C31 C32 C33 58.1(2) . . . . ?
F31B C31 C32 C33 -59.9(2) . . . . ?
I1 C31 C32 C33 178.65(12) . . . . ?
F32A C32 C33 F33A 63.8(2) . . . . ?
F32B C32 C33 F33A -178.03(15) . . . . ?
C31 C32 C33 F33A -57.0(2) . . . . ?
F32A C32 C33 F33B -178.42(15) . . . . ?
F32B C32 C33 F33B -60.2(2) . . . . ?
C31 C32 C33 F33B 60.8(2) . . . . ?
F32A C32 C33 C34 -57.5(2) . . . . ?
F32B C32 C33 C34 60.7(2) . . . . ?
C31 C32 C33 C34 -178.24(16) . . . . ?
F33A C33 C34 F34A -61.47(19) . . . . ?
F33B C33 C34 F34A -179.87(15) . . . . ?
C32 C33 C34 F34A 59.6(2) . . . . ?
F33A C33 C34 F34B -179.25(15) . . . . ?
F33B C33 C34 F34B 62.34(19) . . . . ?
C32 C33 C34 F34B -58.2(2) . . . . ?
F33A C33 C34 C34 59.5(2) . . . 2_656 ?
F33B C33 C34 C34 -58.9(3) . . . 2_656 ?
C32 C33 C34 C34 -179.43(19) . . . 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
N17 H17 O17 0.79(3) 2.21(3) 2.994(2) 169(3) 1_545

_diffrn_measured_fraction_theta_max 0.925
_diffrn_reflns_theta_full        30.00
_diffrn_measured_fraction_theta_full 0.983
_refine_diff_density_max         1.241
_refine_diff_density_min         -1.121
_refine_diff_density_rms         0.114
_database_code_depnum_ccdc_archive 'CCDC 1011552'
#######################################################################
#
#                 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        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H18 N4 O2, C2 F4 I2'
_chemical_formula_sum            'C18 H18 F4 I2 N4 O2'
_chemical_formula_weight         652.16

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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
_SYMMETRY_SPACE_GROUP_NAME_Hall  '-C 2yc '

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

_cell_length_a                   40.059(5)
_cell_length_b                   5.6695(5)
_cell_length_c                   9.7828(12)
_cell_angle_alpha                90.00
_cell_angle_beta                 102.959(3)
_cell_angle_gamma                90.00
_cell_volume                     2165.2(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    90(2)
_cell_measurement_reflns_used    675
_cell_measurement_theta_min      4.18
_cell_measurement_theta_max      26.39

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            COLORLESS
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.001
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1248
_exptl_absorpt_coefficient_mu    2.961
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.5889
_exptl_absorpt_correction_T_max  0.7561
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      90(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            11345
_diffrn_reflns_av_R_equivalents  0.0188
_diffrn_reflns_av_sigmaI/netI    0.0133
_diffrn_reflns_limit_h_min       -50
_diffrn_reflns_limit_h_max       50
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       3
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         3.13
_diffrn_reflns_theta_max         26.43
_reflns_number_total             2229
_reflns_number_gt                1941
_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)+(0.0157P)²+2.6794P] 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         2229
_refine_ls_number_parameters     139
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0179
_refine_ls_R_factor_gt           0.0142
_refine_ls_wR_factor_ref         0.0361
_refine_ls_wR_factor_gt          0.0342
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_restrained_S_all      1.052
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.001

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I 0.803342(3) 0.502546(18) 0.095782(11) 0.01800(5) Uani 1 1 d . . .
F1 F 0.74811(3) 0.5772(2) -0.14886(12) 0.0362(3) Uani 1 1 d . . .
F2 F 0.77760(3) 0.8959(2) -0.08602(13) 0.0359(3) Uani 1 1 d . . .
O1 O 0.94253(3) 0.4305(2) 0.70317(13) 0.0221(3) Uani 1 1 d . . .
N1 N 0.85751(4) 0.2467(3) 0.29288(16) 0.0196(3) Uani 1 1 d . . .
N2 N 0.94835(4) 0.5918(3) 0.49929(15) 0.0162(3) Uani 1 1 d D . .
H2N H 0.9440(5) 0.582(4) 0.4124(16) 0.019 Uiso 1 1 d D . .
C1 C 0.88416(5) 0.3711(3) 0.36465(18) 0.0175(4) Uani 1 1 d . . .
H1A H 0.8900 0.5138 0.3247 0.021 Uiso 1 1 calc R . .
C2 C 0.84972(5) 0.0460(3) 0.3506(2) 0.0215(4) Uani 1 1 d . . .
H2A H 0.8310 -0.0448 0.3004 0.026 Uiso 1 1 calc R . .
C3 C 0.86750(5) -0.0362(3) 0.4798(2) 0.0227(4) Uani 1 1 d . . .
H3A H 0.8611 -0.1798 0.5170 0.027 Uiso 1 1 calc R . .
C4 C 0.89475(5) 0.0953(3) 0.55350(19) 0.0199(4) Uani 1 1 d . . .
H4A H 0.9071 0.0446 0.6432 0.024 Uiso 1 1 calc R . .
C5 C 0.90381(4) 0.3022(3) 0.49485(18) 0.0153(3) Uani 1 1 d . . .
C6 C 0.93311(5) 0.4461(3) 0.57395(18) 0.0160(3) Uani 1 1 d . . .
C7 C 0.97620(5) 0.7456(3) 0.56848(18) 0.0173(4) Uani 1 1 d . . .
H7A H 0.9964 0.6489 0.6117 0.021 Uiso 1 1 calc R . .
H7B H 0.9691 0.8351 0.6440 0.021 Uiso 1 1 calc R . .
C8 C 0.98581(5) 0.9167(3) 0.46391(18) 0.0177(4) Uani 1 1 d . . .
H8A H 0.9654 1.0096 0.4186 0.021 Uiso 1 1 calc R . .
H8B H 0.9936 0.8270 0.3900 0.021 Uiso 1 1 calc R . .
C9 C 0.76354(5) 0.7076(3) -0.03770(18) 0.0199(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
I1 C9 2.1597(18) . ?
F1 C9 1.345(2) . ?
F2 C9 1.342(2) . ?
O1 C6 1.239(2) . ?
N1 C2 1.338(2) . ?
N1 C1 1.339(2) . ?
N2 C6 1.337(2) . ?
N2 C7 1.457(2) . ?
N2 H2N 0.830(15) . ?
C1 C5 1.395(2) . ?
C1 H1A 0.9500 . ?
C2 C3 1.385(3) . ?
C2 H2A 0.9500 . ?
C3 C4 1.383(3) . ?
C3 H3A 0.9500 . ?
C4 C5 1.389(2) . ?
C4 H4A 0.9500 . ?
C5 C6 1.495(2) . ?
C7 C8 1.521(2) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C8 1.524(3) 5_776 ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C9 1.520(4) 7_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
C2 N1 C1 117.42(16) . . ?
C6 N2 C7 120.76(15) . . ?
C6 N2 H2N 120.0(15) . . ?
C7 N2 H2N 118.6(15) . . ?
N1 C1 C5 123.47(16) . . ?
N1 C1 H1A 118.3 . . ?
C5 C1 H1A 118.3 . . ?
N1 C2 C3 123.39(17) . . ?
N1 C2 H2A 118.3 . . ?
C3 C2 H2A 118.3 . . ?
C4 C3 C2 118.60(17) . . ?
C4 C3 H3A 120.7 . . ?
C2 C3 H3A 120.7 . . ?
C3 C4 C5 119.22(17) . . ?
C3 C4 H4A 120.4 . . ?
C5 C4 H4A 120.4 . . ?
C4 C5 C1 117.88(16) . . ?
C4 C5 C6 119.64(16) . . ?
C1 C5 C6 122.45(15) . . ?
O1 C6 N2 121.97(16) . . ?
O1 C6 C5 120.89(16) . . ?
N2 C6 C5 117.14(15) . . ?
N2 C7 C8 110.62(14) . . ?
N2 C7 H7A 109.5 . . ?
C8 C7 H7A 109.5 . . ?
N2 C7 H7B 109.5 . . ?
C8 C7 H7B 109.5 . . ?
H7A C7 H7B 108.1 . . ?
C7 C8 C8 111.03(18) . 5_776 ?
C7 C8 H8A 109.4 . . ?
C8 C8 H8A 109.4 5_776 . ?
C7 C8 H8B 109.4 . . ?
C8 C8 H8B 109.4 5_776 . ?
H8A C8 H8B 108.0 . . ?
F2 C9 F1 107.79(15) . . ?
F2 C9 C9 108.70(18) . 7_665 ?
F1 C9 C9 108.50(18) . 7_665 ?
F2 C9 I1 109.28(12) . . ?
F1 C9 I1 109.65(12) . . ?
C9 C9 I1 112.79(16) 7_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
C2 N1 C1 C5 -0.1(3) . . . . ?
C1 N1 C2 C3 0.6(3) . . . . ?
N1 C2 C3 C4 0.0(3) . . . . ?
C2 C3 C4 C5 -1.2(3) . . . . ?
C3 C4 C5 C1 1.7(3) . . . . ?
C3 C4 C5 C6 179.71(16) . . . . ?
N1 C1 C5 C4 -1.1(3) . . . . ?
N1 C1 C5 C6 -179.02(16) . . . . ?
C7 N2 C6 O1 -2.1(3) . . . . ?
C7 N2 C6 C5 177.48(15) . . . . ?
C4 C5 C6 O1 -22.8(3) . . . . ?
C1 C5 C6 O1 155.13(17) . . . . ?
C4 C5 C6 N2 157.58(17) . . . . ?
C1 C5 C6 N2 -24.5(2) . . . . ?
C6 N2 C7 C8 -172.19(16) . . . . ?
N2 C7 C8 C8 178.27(18) . . . 5_776 ?

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
N2 H2N O1 0.830(15) 2.036(15) 2.8565(19) 170(2) 6_565

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.388
_refine_diff_density_min         -0.287
_refine_diff_density_rms         0.058
_database_code_depnum_ccdc_archive 'CCDC 1011553'
#######################################################################
#
#                 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_A4D4

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H18 N4 O2, C4 F8 I2 '
_chemical_formula_sum            'C20 H18 F8 I2 N4 O2'
_chemical_formula_weight         752.18

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1
_symmetry_space_group_name_Hall  '-P 1'

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

_cell_length_a                   4.9772(12)
_cell_length_b                   10.655(3)
_cell_length_c                   12.169(3)
_cell_angle_alpha                71.067(2)
_cell_angle_beta                 88.865(3)
_cell_angle_gamma                86.924(2)
_cell_volume                     609.6(3)
_cell_formula_units_Z            1
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    5012
_cell_measurement_theta_min      2.21
_cell_measurement_theta_max      26.30

_exptl_crystal_description       PLATE
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.049
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             360
_exptl_absorpt_coefficient_mu    2.667
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5017
_exptl_absorpt_correction_T_max  0.7763
_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            9444
_diffrn_reflns_av_R_equivalents  0.0332
_diffrn_reflns_av_sigmaI/netI    0.0311
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_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         1.77
_diffrn_reflns_theta_max         26.47
_reflns_number_total             2518
_reflns_number_gt                2295
_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)+(0.0225P)²+0.4808P] 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         2518
_refine_ls_number_parameters     166
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0269
_refine_ls_R_factor_gt           0.0225
_refine_ls_wR_factor_ref         0.0525
_refine_ls_wR_factor_gt          0.0498
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_restrained_S_all      1.021
_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
I1 I 0.42092(4) 0.784616(18) 0.806575(16) 0.02345(7) Uani 1 1 d . . .
F1 F 0.7685(4) 0.9918(2) 0.81967(16) 0.0381(5) Uani 1 1 d . . .
F2 F 0.3512(4) 1.06271(16) 0.78828(15) 0.0335(4) Uani 1 1 d . . .
F3 F 0.6417(3) 0.83699(16) 1.03965(14) 0.0262(4) Uani 1 1 d . . .
F4 F 0.2195(3) 0.90447(16) 1.00883(14) 0.0234(4) Uani 1 1 d . . .
O1 O 0.4650(4) 0.3170(2) 0.56792(17) 0.0227(4) Uani 1 1 d . . .
N1 N 0.2200(5) 0.5616(2) 0.7626(2) 0.0246(5) Uani 1 1 d . . .
N2 N 0.0337(5) 0.2644(2) 0.5557(2) 0.0193(5) Uani 1 1 d D . .
H2N H -0.130(4) 0.276(3) 0.572(3) 0.023 Uiso 1 1 d D . .
C1 C 0.2768(6) 0.4978(3) 0.6864(2) 0.0217(6) Uani 1 1 d . . .
H1A H 0.4199 0.5273 0.6330 0.026 Uiso 1 1 calc R . .
C2 C 0.0179(6) 0.5186(3) 0.8374(3) 0.0236(6) Uani 1 1 d . . .
H2A H -0.0248 0.5637 0.8917 0.028 Uiso 1 1 calc R . .
C3 C -0.1317(6) 0.4126(3) 0.8399(3) 0.0249(6) Uani 1 1 d . . .
H3A H -0.2725 0.3849 0.8950 0.030 Uiso 1 1 calc R . .
C4 C -0.0716(6) 0.3472(3) 0.7601(2) 0.0216(6) Uani 1 1 d . . .
H4A H -0.1717 0.2740 0.7593 0.026 Uiso 1 1 calc R . .
C5 C 0.1365(5) 0.3900(3) 0.6813(2) 0.0173(5) Uani 1 1 d . . .
C6 C 0.2256(5) 0.3210(3) 0.5960(2) 0.0175(5) Uani 1 1 d . . .
C7 C 0.0918(6) 0.1798(3) 0.4847(3) 0.0223(6) Uani 1 1 d . . .
H7A H 0.2891 0.1651 0.4794 0.027 Uiso 1 1 calc R . .
H7B H 0.0225 0.2249 0.4052 0.027 Uiso 1 1 calc R . .
C8 C -0.0353(6) 0.0466(3) 0.5350(2) 0.0199(6) Uani 1 1 d . . .
H8A H -0.2333 0.0614 0.5366 0.024 Uiso 1 1 calc R . .
H8B H 0.0265 0.0040 0.6161 0.024 Uiso 1 1 calc R . .
C9 C 0.5144(6) 0.9593(3) 0.8496(2) 0.0213(6) Uani 1 1 d . . .
C10 C 0.4742(5) 0.9394(3) 0.9797(2) 0.0186(6) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I1 C9 2.166(3) . ?
F1 C9 1.341(3) . ?
F2 C9 1.351(3) . ?
F3 C10 1.352(3) . ?
F4 C10 1.349(3) . ?
O1 C6 1.236(3) . ?
N1 C1 1.334(4) . ?
N1 C2 1.339(4) . ?
N2 C6 1.337(3) . ?
N2 C7 1.453(3) . ?
N2 H2N 0.844(17) . ?
C1 C5 1.395(4) . ?
C1 H1A 0.9500 . ?
C2 C3 1.377(4) . ?
C2 H2A 0.9500 . ?
C3 C4 1.388(4) . ?
C3 H3A 0.9500 . ?
C4 C5 1.389(4) . ?
C4 H4A 0.9500 . ?
C5 C6 1.502(4) . ?
C7 C8 1.518(4) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C8 1.529(5) 2_556 ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.538(4) . ?
C10 C10 1.561(5) 2_677 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C2 117.5(2) . . ?
C6 N2 C7 122.9(2) . . ?
C6 N2 H2N 121(2) . . ?
C7 N2 H2N 117(2) . . ?
N1 C1 C5 123.3(3) . . ?
N1 C1 H1A 118.3 . . ?
C5 C1 H1A 118.3 . . ?
N1 C2 C3 123.7(3) . . ?
N1 C2 H2A 118.2 . . ?
C3 C2 H2A 118.2 . . ?
C2 C3 C4 118.4(3) . . ?
C2 C3 H3A 120.8 . . ?
C4 C3 H3A 120.8 . . ?
C3 C4 C5 119.2(3) . . ?
C3 C4 H4A 120.4 . . ?
C5 C4 H4A 120.4 . . ?
C4 C5 C1 118.0(2) . . ?
C4 C5 C6 122.9(2) . . ?
C1 C5 C6 119.0(2) . . ?
O1 C6 N2 123.5(2) . . ?
O1 C6 C5 120.2(2) . . ?
N2 C6 C5 116.2(2) . . ?
N2 C7 C8 111.5(2) . . ?
N2 C7 H7A 109.3 . . ?
C8 C7 H7A 109.3 . . ?
N2 C7 H7B 109.3 . . ?
C8 C7 H7B 109.3 . . ?
H7A C7 H7B 108.0 . . ?
C7 C8 C8 112.3(3) . 2_556 ?
C7 C8 H8A 109.1 . . ?
C8 C8 H8A 109.1 2_556 . ?
C7 C8 H8B 109.1 . . ?
C8 C8 H8B 109.1 2_556 . ?
H8A C8 H8B 107.9 . . ?
F1 C9 F2 107.4(2) . . ?
F1 C9 C10 109.2(2) . . ?
F2 C9 C10 108.6(2) . . ?
F1 C9 I1 110.67(18) . . ?
F2 C9 I1 108.93(17) . . ?
C10 C9 I1 111.98(18) . . ?
F4 C10 F3 107.9(2) . . ?
F4 C10 C9 108.4(2) . . ?
F3 C10 C9 107.8(2) . . ?
F4 C10 C10 107.8(3) . 2_677 ?
F3 C10 C10 107.9(3) . 2_677 ?
C9 C10 C10 116.6(3) . 2_677 ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C2 N1 C1 C5 0.1(4) . . . . ?
C1 N1 C2 C3 0.3(4) . . . . ?
N1 C2 C3 C4 -0.6(5) . . . . ?
C2 C3 C4 C5 0.3(4) . . . . ?
C3 C4 C5 C1 0.0(4) . . . . ?
C3 C4 C5 C6 176.6(3) . . . . ?
N1 C1 C5 C4 -0.3(4) . . . . ?
N1 C1 C5 C6 -177.0(3) . . . . ?
C7 N2 C6 O1 7.0(4) . . . . ?
C7 N2 C6 C5 -171.9(2) . . . . ?
C4 C5 C6 O1 -146.1(3) . . . . ?
C1 C5 C6 O1 30.4(4) . . . . ?
C4 C5 C6 N2 32.8(4) . . . . ?
C1 C5 C6 N2 -150.6(3) . . . . ?
C6 N2 C7 C8 126.8(3) . . . . ?
N2 C7 C8 C8 -177.1(3) . . . 2_556 ?
F1 C9 C10 F4 -178.9(2) . . . . ?
F2 C9 C10 F4 64.3(3) . . . . ?
I1 C9 C10 F4 -56.0(2) . . . . ?
F1 C9 C10 F3 -62.3(3) . . . . ?
F2 C9 C10 F3 -179.1(2) . . . . ?
I1 C9 C10 F3 60.6(2) . . . . ?
F1 C9 C10 C10 59.2(4) . . . 2_677 ?
F2 C9 C10 C10 -57.6(4) . . . 2_677 ?
I1 C9 C10 C10 -177.9(2) . . . 2_677 ?

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
N2 H2N O1 0.844(17) 2.040(19) 2.866(3) 166(3) 1_455

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.789
_refine_diff_density_min         -0.491
_refine_diff_density_rms         0.091
_database_code_depnum_ccdc_archive 'CCDC 1011554'
#######################################################################
#
#                 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_A4D6

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
DW-6-9 (3-pyridyl)-COHN-(CH2)4-NHCO-(3-pyridyl), I-(CF2)6-I
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         
;
(C16 H18 N4 O2) (C6 F12 I2)
;
_chemical_formula_sum            'C22 H18 F12 I2 N4 O2'
_chemical_formula_weight         852.20

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           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                   49.953(3)
_cell_length_b                   5.5707(3)
_cell_length_c                   9.7257(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 95.234(2)
_cell_angle_gamma                90.00
_cell_volume                     2695.1(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    9861
_cell_measurement_theta_min      2.19
_cell_measurement_theta_max      33.63

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.100
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1632
_exptl_absorpt_coefficient_mu    2.447
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4901
_exptl_absorpt_correction_T_max  0.6671
_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            21607
_diffrn_reflns_av_R_equivalents  0.0206
_diffrn_reflns_av_sigmaI/netI    0.0168
_diffrn_reflns_limit_h_min       -76
_diffrn_reflns_limit_h_max       70
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.46
_diffrn_reflns_theta_max         33.12
_reflns_number_total             4804
_reflns_number_gt                4604
_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+4.0000P] 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         4804
_refine_ls_number_parameters     190
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0233
_refine_ls_R_factor_gt           0.0220
_refine_ls_wR_factor_ref         0.0574
_refine_ls_wR_factor_gt          0.0567
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_restrained_S_all      1.033
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I 0.156213(2) 0.527718(19) 0.291382(10) 0.02308(4) Uani 1 1 d . . .
N11 N 0.11302(3) 0.2535(3) 0.12841(14) 0.0244(3) Uani 1 1 d . . .
C12 C 0.09183(3) 0.3755(3) 0.07231(15) 0.0201(2) Uani 1 1 d . . .
H12 H 0.0870 0.5196 0.1160 0.024 Uiso 1 1 calc R . .
C13 C 0.07642(3) 0.3029(3) -0.04704(14) 0.0177(2) Uani 1 1 d . . .
C14 C 0.08394(3) 0.0942(3) -0.11180(17) 0.0233(3) Uani 1 1 d . . .
H14 H 0.0742 0.0405 -0.1945 0.028 Uiso 1 1 calc R . .
C15 C 0.10582(4) -0.0339(3) -0.0539(2) 0.0277(3) Uani 1 1 d . . .
H15 H 0.1113 -0.1781 -0.0954 0.033 Uiso 1 1 calc R . .
C16 C 0.11965(3) 0.0520(3) 0.06588(19) 0.0267(3) Uani 1 1 d . . .
H16 H 0.1346 -0.0372 0.1055 0.032 Uiso 1 1 calc R . .
C17 C 0.05321(3) 0.4444(3) -0.11015(15) 0.0178(2) Uani 1 1 d . . .
N17 N 0.04104(3) 0.5913(2) -0.02703(12) 0.0192(2) Uani 1 1 d . . .
H17 H 0.0464 0.5953 0.0617 0.023 Uiso 1 1 calc R . .
O17 O 0.04566(2) 0.4258(3) -0.23414(11) 0.0263(2) Uani 1 1 d . . .
C21 C 0.01908(3) 0.7446(3) -0.08161(14) 0.0196(2) Uani 1 1 d . . .
H21A H 0.0034 0.6445 -0.1140 0.023 Uiso 1 1 calc R . .
H21B H 0.0246 0.8364 -0.1615 0.023 Uiso 1 1 calc R . .
C22 C 0.01128(3) 0.9172(3) 0.02848(15) 0.0199(2) Uani 1 1 d . . .
H22A H 0.0271 1.0143 0.0625 0.024 Uiso 1 1 calc R . .
H22B H 0.0054 0.8252 0.1074 0.024 Uiso 1 1 calc R . .
C31 C 0.18641(3) 0.7716(3) 0.38021(18) 0.0251(3) Uani 1 1 d . . .
F31A F 0.17824(2) 0.8752(3) 0.49190(15) 0.0500(4) Uani 1 1 d . . .
F31B F 0.18964(3) 0.9444(2) 0.28749(18) 0.0514(4) Uani 1 1 d . . .
C32 C 0.21360(3) 0.6462(3) 0.41778(15) 0.0208(3) Uani 1 1 d . . .
F32A F 0.20940(3) 0.4664(2) 0.50449(15) 0.0394(3) Uani 1 1 d . . .
F32B F 0.22161(2) 0.5537(3) 0.30226(13) 0.0423(3) Uani 1 1 d . . .
C33 C 0.23606(3) 0.8111(3) 0.48644(15) 0.0202(3) Uani 1 1 d . . .
F33A F 0.22827(2) 0.8848(3) 0.60744(11) 0.0358(3) Uani 1 1 d . . .
F33B F 0.23864(2) 1.0023(2) 0.40623(15) 0.0364(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
I1 C31 2.1519(16) . ?
I1 N11 2.9793(14) . ?
N11 C12 1.3324(19) . ?
N11 C16 1.333(2) . ?
C12 C13 1.393(2) . ?
C12 H12 0.9500 . ?
C13 C14 1.391(2) . ?
C13 C17 1.487(2) . ?
C14 C15 1.381(2) . ?
C14 H14 0.9500 . ?
C15 C16 1.384(3) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 O17 1.2346(18) . ?
C17 N17 1.3353(18) . ?
N17 C21 1.4518(18) . ?
N17 H17 0.8800 . ?
C21 C22 1.516(2) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 C22 1.521(3) 5_575 ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C31 F31A 1.327(2) . ?
C31 F31B 1.339(2) . ?
C31 C32 1.541(2) . ?
C32 F32B 1.3304(18) . ?
C32 F32A 1.3378(19) . ?
C32 C33 1.553(2) . ?
C33 F33B 1.3335(18) . ?
C33 F33A 1.3372(17) . ?
C33 C33 1.552(3) 7_566 ?

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
C31 I1 N11 169.88(5) . . ?
C12 N11 C16 117.65(14) . . ?
C12 N11 I1 117.78(10) . . ?
C16 N11 I1 118.46(10) . . ?
N11 C12 C13 123.45(14) . . ?
N11 C12 H12 118.3 . . ?
C13 C12 H12 118.3 . . ?
C14 C13 C12 117.95(13) . . ?
C14 C13 C17 119.26(13) . . ?
C12 C13 C17 122.73(13) . . ?
C15 C14 C13 118.92(15) . . ?
C15 C14 H14 120.5 . . ?
C13 C14 H14 120.5 . . ?
C14 C15 C16 118.70(15) . . ?
C14 C15 H15 120.7 . . ?
C16 C15 H15 120.7 . . ?
N11 C16 C15 123.32(15) . . ?
N11 C16 H16 118.3 . . ?
C15 C16 H16 118.3 . . ?
O17 C17 N17 121.81(14) . . ?
O17 C17 C13 121.07(13) . . ?
N17 C17 C13 117.12(12) . . ?
C17 N17 C21 120.65(12) . . ?
C17 N17 H17 119.7 . . ?
C21 N17 H17 119.7 . . ?
N17 C21 C22 110.44(11) . . ?
N17 C21 H21A 109.6 . . ?
C22 C21 H21A 109.6 . . ?
N17 C21 H21B 109.6 . . ?
C22 C21 H21B 109.6 . . ?
H21A C21 H21B 108.1 . . ?
C21 C22 C22 110.92(15) . 5_575 ?
C21 C22 H22A 109.5 . . ?
C22 C22 H22A 109.5 5_575 . ?
C21 C22 H22B 109.5 . . ?
C22 C22 H22B 109.5 5_575 . ?
H22A C22 H22B 108.0 . . ?
F31A C31 F31B 107.68(16) . . ?
F31A C31 C32 109.47(14) . . ?
F31B C31 C32 109.16(13) . . ?
F31A C31 I1 110.28(11) . . ?
F31B C31 I1 107.85(11) . . ?
C32 C31 I1 112.28(11) . . ?
F32B C32 F32A 108.60(14) . . ?
F32B C32 C31 107.57(13) . . ?
F32A C32 C31 107.67(13) . . ?
F32B C32 C33 109.33(13) . . ?
F32A C32 C33 108.69(12) . . ?
C31 C32 C33 114.83(13) . . ?
F33B C33 F33A 108.74(14) . . ?
F33B C33 C33 108.47(15) . 7_566 ?
F33A C33 C33 108.29(15) . 7_566 ?
F33B C33 C32 109.01(12) . . ?
F33A C33 C32 107.64(12) . . ?
C33 C33 C32 114.55(15) 7_566 . ?

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
C31 I1 N11 C12 -42.4(3) . . . . ?
C31 I1 N11 C16 109.5(3) . . . . ?
C16 N11 C12 C13 0.1(2) . . . . ?
I1 N11 C12 C13 152.29(11) . . . . ?
N11 C12 C13 C14 -1.1(2) . . . . ?
N11 C12 C13 C17 -178.49(14) . . . . ?
C12 C13 C14 C15 1.4(2) . . . . ?
C17 C13 C14 C15 178.83(14) . . . . ?
C13 C14 C15 C16 -0.7(2) . . . . ?
C12 N11 C16 C15 0.6(2) . . . . ?
I1 N11 C16 C15 -151.36(13) . . . . ?
C14 C15 C16 N11 -0.3(3) . . . . ?
C14 C13 C17 O17 -21.8(2) . . . . ?
C12 C13 C17 O17 155.49(15) . . . . ?
C14 C13 C17 N17 158.18(14) . . . . ?
C12 C13 C17 N17 -24.5(2) . . . . ?
O17 C17 N17 C21 -3.1(2) . . . . ?
C13 C17 N17 C21 176.93(13) . . . . ?
C17 N17 C21 C22 -172.29(13) . . . . ?
N17 C21 C22 C22 178.67(15) . . . 5_575 ?
N11 I1 C31 F31A 109.7(3) . . . . ?
N11 I1 C31 F31B -7.7(4) . . . . ?
N11 I1 C31 C32 -128.0(3) . . . . ?
F31A C31 C32 F32B -177.39(15) . . . . ?
F31B C31 C32 F32B -59.76(18) . . . . ?
I1 C31 C32 F32B 59.78(15) . . . . ?
F31A C31 C32 F32A 65.74(17) . . . . ?
F31B C31 C32 F32A -176.63(15) . . . . ?
I1 C31 C32 F32A -57.09(15) . . . . ?
F31A C31 C32 C33 -55.46(18) . . . . ?
F31B C31 C32 C33 62.18(18) . . . . ?
I1 C31 C32 C33 -178.28(10) . . . . ?
F32B C32 C33 F33B 67.24(16) . . . . ?
F32A C32 C33 F33B -174.37(13) . . . . ?
C31 C32 C33 F33B -53.73(17) . . . . ?
F32B C32 C33 F33A -174.97(13) . . . . ?
F32A C32 C33 F33A -56.58(17) . . . . ?
C31 C32 C33 F33A 64.05(17) . . . . ?
F32B C32 C33 C33 -54.5(2) . . . 7_566 ?
F32A C32 C33 C33 63.91(19) . . . 7_566 ?
C31 C32 C33 C33 -175.46(15) . . . 7_566 ?

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
N17 H17 O17 0.88 1.99 2.8384(16) 160.8 6_566

_diffrn_measured_fraction_theta_max 0.934
_diffrn_reflns_theta_full        30.00
_diffrn_measured_fraction_theta_full 0.989
_refine_diff_density_max         0.692
_refine_diff_density_min         -0.798
_refine_diff_density_rms         0.096
_database_code_depnum_ccdc_archive 'CCDC 1011555'
#######################################################################
#
#                 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        
;
DW-6-18  (3-pyridyl)-COHN-(CH2)4-NHCO-(3-pyridyl), I-(CF2)8-I
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         
;
(C16 H18 N4 O2) (C8 F16 I2)
;
_chemical_formula_sum            'C24 H18 F16 I2 N4 O2'
_chemical_formula_weight         952.22

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           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                   54.569(3)
_cell_length_b                   5.6337(3)
_cell_length_c                   9.7038(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 92.370(2)
_cell_angle_gamma                90.00
_cell_volume                     2980.6(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    9957
_cell_measurement_theta_min      2.99
_cell_measurement_theta_max      32.59

_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    2.122
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1824
_exptl_absorpt_coefficient_mu    2.243
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5932
_exptl_absorpt_correction_T_max  0.8772
_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            16963
_diffrn_reflns_av_R_equivalents  0.0242
_diffrn_reflns_av_sigmaI/netI    0.0249
_diffrn_reflns_limit_h_min       -77
_diffrn_reflns_limit_h_max       82
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         1.49
_diffrn_reflns_theta_max         32.56
_reflns_number_total             4886
_reflns_number_gt                4249
_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+3.0000P] 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         4886
_refine_ls_number_parameters     220
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0326
_refine_ls_R_factor_gt           0.0266
_refine_ls_wR_factor_ref         0.0641
_refine_ls_wR_factor_gt          0.0618
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_restrained_S_all      1.070
_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 0.10261(3) -0.7477(3) 0.60843(17) 0.0280(3) Uani 1 1 d . . .
C12 C 0.08335(3) -0.6258(3) 0.55566(19) 0.0239(3) Uani 1 1 d . . .
H12 H 0.0790 -0.4821 0.5995 0.029 Uiso 1 1 calc R . .
C13 C 0.06941(3) -0.6985(3) 0.43997(18) 0.0218(3) Uani 1 1 d . . .
C14 C 0.07621(4) -0.9070(4) 0.3743(2) 0.0272(4) Uani 1 1 d . . .
H14 H 0.0674 -0.9605 0.2938 0.033 Uiso 1 1 calc R . .
C15 C 0.09599(4) -1.0344(4) 0.4285(2) 0.0315(4) Uani 1 1 d . . .
H15 H 0.1009 -1.1782 0.3865 0.038 Uiso 1 1 calc R . .
C16 C 0.10861(4) -0.9492(4) 0.5451(2) 0.0302(4) Uani 1 1 d . . .
H16 H 0.1222 -1.0380 0.5818 0.036 Uiso 1 1 calc R . .
C17 C 0.04826(3) -0.5573(3) 0.38083(19) 0.0218(3) Uani 1 1 d . . .
N17 N 0.03733(3) -0.4085(3) 0.46543(16) 0.0232(3) Uani 1 1 d . . .
H17 H 0.0404(5) -0.417(5) 0.551(3) 0.028 Uiso 1 1 d . . .
O17 O 0.04139(3) -0.5789(3) 0.25854(14) 0.0299(3) Uani 1 1 d . . .
C21 C 0.01739(3) -0.2554(3) 0.41508(18) 0.0238(3) Uani 1 1 d . . .
H21A H 0.0030 -0.3537 0.3863 0.029 Uiso 1 1 calc R . .
H21B H 0.0226 -0.1658 0.3336 0.029 Uiso 1 1 calc R . .
C22 C 0.01017(3) -0.0828(4) 0.52638(19) 0.0241(3) Uani 1 1 d . . .
H22A H 0.0247 0.0121 0.5570 0.029 Uiso 1 1 calc R . .
H22B H 0.0045 -0.1726 0.6068 0.029 Uiso 1 1 calc R . .
C31 C 0.16986(3) -0.2342(3) 0.8373(2) 0.0260(4) Uani 1 1 d . . .
F31A F 0.16212(2) -0.1170(3) 0.94749(15) 0.0395(3) Uani 1 1 d . . .
F31B F 0.17373(3) -0.0739(3) 0.73865(16) 0.0417(3) Uani 1 1 d . . .
I1 I 0.141970(2) -0.47715(2) 0.759701(13) 0.02588(5) Uani 1 1 d . . .
C32 C 0.19408(3) -0.3623(3) 0.87777(19) 0.0232(3) Uani 1 1 d . . .
F32A F 0.18909(2) -0.5340(2) 0.96783(15) 0.0345(3) Uani 1 1 d . . .
F32B F 0.20263(2) -0.4620(3) 0.76388(14) 0.0366(3) Uani 1 1 d . . .
C33 C 0.21449(3) -0.1996(3) 0.94480(18) 0.0227(3) Uani 1 1 d . . .
F33A F 0.21589(3) 0.0002(2) 0.87055(16) 0.0368(3) Uani 1 1 d . . .
F33B F 0.20764(2) -0.1425(3) 1.07130(12) 0.0345(3) Uani 1 1 d . . .
C34 C 0.24031(3) -0.3160(3) 0.95385(19) 0.0243(3) Uani 1 1 d . . .
F34A F 0.23829(3) -0.5367(2) 1.00108(19) 0.0442(4) Uani 1 1 d . . .
F34B F 0.24835(2) -0.3239(3) 0.82540(13) 0.0476(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
N11 C16 1.338(3) . ?
N11 C12 1.339(2) . ?
N11 I1 2.9716(17) . ?
C12 C13 1.391(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.393(3) . ?
C13 C17 1.497(3) . ?
C14 C15 1.382(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.385(3) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 O17 1.235(2) . ?
C17 N17 1.331(2) . ?
N17 C21 1.457(2) . ?
N17 H17 0.84(3) . ?
C21 C22 1.517(3) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 C22 1.523(4) 5_556 ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C31 F31B 1.339(2) . ?
C31 F31A 1.340(2) . ?
C31 C32 1.542(3) . ?
C31 I1 2.1592(19) . ?
C32 F32A 1.339(2) . ?
C32 F32B 1.341(2) . ?
C32 C33 1.563(3) . ?
C33 F33B 1.337(2) . ?
C33 F33A 1.341(2) . ?
C33 C34 1.553(3) . ?
C34 F34A 1.331(2) . ?
C34 F34B 1.339(2) . ?
C34 C34 1.548(4) 7_547 ?

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 117.53(18) . . ?
C16 N11 I1 118.45(13) . . ?
C12 N11 I1 117.76(13) . . ?
N11 C12 C13 123.50(18) . . ?
N11 C12 H12 118.3 . . ?
C13 C12 H12 118.3 . . ?
C12 C13 C14 118.02(17) . . ?
C12 C13 C17 122.70(16) . . ?
C14 C13 C17 119.23(17) . . ?
C15 C14 C13 118.84(19) . . ?
C15 C14 H14 120.6 . . ?
C13 C14 H14 120.6 . . ?
C14 C15 C16 118.97(19) . . ?
C14 C15 H15 120.5 . . ?
C16 C15 H15 120.5 . . ?
N11 C16 C15 123.13(19) . . ?
N11 C16 H16 118.4 . . ?
C15 C16 H16 118.4 . . ?
O17 C17 N17 121.90(17) . . ?
O17 C17 C13 120.96(17) . . ?
N17 C17 C13 117.14(16) . . ?
C17 N17 C21 120.88(16) . . ?
C17 N17 H17 119.9(18) . . ?
C21 N17 H17 118.6(18) . . ?
N17 C21 C22 110.67(15) . . ?
N17 C21 H21A 109.5 . . ?
C22 C21 H21A 109.5 . . ?
N17 C21 H21B 109.5 . . ?
C22 C21 H21B 109.5 . . ?
H21A C21 H21B 108.1 . . ?
C21 C22 C22 111.13(19) . 5_556 ?
C21 C22 H22A 109.4 . . ?
C22 C22 H22A 109.4 5_556 . ?
C21 C22 H22B 109.4 . . ?
C22 C22 H22B 109.4 5_556 . ?
H22A C22 H22B 108.0 . . ?
F31B C31 F31A 107.59(17) . . ?
F31B C31 C32 109.83(16) . . ?
F31A C31 C32 108.80(15) . . ?
F31B C31 I1 107.94(13) . . ?
F31A C31 I1 110.45(12) . . ?
C32 C31 I1 112.12(13) . . ?
C31 I1 N11 169.13(6) . . ?
F32A C32 F32B 108.81(16) . . ?
F32A C32 C31 108.01(15) . . ?
F32B C32 C31 108.03(15) . . ?
F32A C32 C33 108.21(15) . . ?
F32B C32 C33 108.82(15) . . ?
C31 C32 C33 114.83(15) . . ?
F33B C33 F33A 108.42(16) . . ?
F33B C33 C34 109.69(14) . . ?
F33A C33 C34 108.25(15) . . ?
F33B C33 C32 107.56(15) . . ?
F33A C33 C32 108.93(15) . . ?
C34 C33 C32 113.88(15) . . ?
F34A C34 F34B 108.92(17) . . ?
F34A C34 C34 108.3(2) . 7_547 ?
F34B C34 C34 108.19(19) . 7_547 ?
F34A C34 C33 109.04(16) . . ?
F34B C34 C33 107.03(15) . . ?
C34 C34 C33 115.24(19) 7_547 . ?

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 0.3(3) . . . . ?
I1 N11 C12 C13 152.13(15) . . . . ?
N11 C12 C13 C14 -1.3(3) . . . . ?
N11 C12 C13 C17 -178.72(17) . . . . ?
C12 C13 C14 C15 1.5(3) . . . . ?
C17 C13 C14 C15 179.05(18) . . . . ?
C13 C14 C15 C16 -0.9(3) . . . . ?
C12 N11 C16 C15 0.4(3) . . . . ?
I1 N11 C16 C15 -151.21(17) . . . . ?
C14 C15 C16 N11 -0.1(3) . . . . ?
C12 C13 C17 O17 156.12(19) . . . . ?
C14 C13 C17 O17 -21.3(3) . . . . ?
C12 C13 C17 N17 -23.8(3) . . . . ?
C14 C13 C17 N17 158.81(18) . . . . ?
O17 C17 N17 C21 -3.0(3) . . . . ?
C13 C17 N17 C21 176.90(16) . . . . ?
C17 N17 C21 C22 -173.15(17) . . . . ?
N17 C21 C22 C22 178.4(2) . . . 5_556 ?
F31B C31 I1 N11 -8.1(4) . . . . ?
F31A C31 I1 N11 109.3(3) . . . . ?
C32 C31 I1 N11 -129.2(3) . . . . ?
C16 N11 I1 C31 106.7(3) . . . . ?
C12 N11 I1 C31 -44.9(4) . . . . ?
F31B C31 C32 F32A -174.93(16) . . . . ?
F31A C31 C32 F32A 67.5(2) . . . . ?
I1 C31 C32 F32A -54.93(17) . . . . ?
F31B C31 C32 F32B -57.4(2) . . . . ?
F31A C31 C32 F32B -174.93(15) . . . . ?
I1 C31 C32 F32B 62.61(17) . . . . ?
F31B C31 C32 C33 64.2(2) . . . . ?
F31A C31 C32 C33 -53.3(2) . . . . ?
I1 C31 C32 C33 -175.76(12) . . . . ?
F32A C32 C33 F33B -49.19(19) . . . . ?
F32B C32 C33 F33B -167.28(15) . . . . ?
C31 C32 C33 F33B 71.5(2) . . . . ?
F32A C32 C33 F33A -166.50(15) . . . . ?
F32B C32 C33 F33A 75.41(19) . . . . ?
C31 C32 C33 F33A -45.8(2) . . . . ?
F32A C32 C33 C34 72.58(19) . . . . ?
F32B C32 C33 C34 -45.5(2) . . . . ?
C31 C32 C33 C34 -166.70(15) . . . . ?
F33B C33 C34 F34A 74.91(19) . . . . ?
F33A C33 C34 F34A -166.96(16) . . . . ?
C32 C33 C34 F34A -45.7(2) . . . . ?
F33B C33 C34 F34B -167.41(16) . . . . ?
F33A C33 C34 F34B -49.3(2) . . . . ?
C32 C33 C34 F34B 72.0(2) . . . . ?
F33B C33 C34 C34 -47.1(3) . . . 7_547 ?
F33A C33 C34 C34 71.1(2) . . . 7_547 ?
C32 C33 C34 C34 -167.7(2) . . . 7_547 ?

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
N17 H17 O17 0.84(3) 2.01(3) 2.845(2) 170(2) 6_546

_diffrn_measured_fraction_theta_max 0.899
_diffrn_reflns_theta_full        30.00
_diffrn_measured_fraction_theta_full 0.980
_refine_diff_density_max         0.620
_refine_diff_density_min         -0.843
_refine_diff_density_rms         0.090
_database_code_depnum_ccdc_archive 'CCDC 1011556'
#######################################################################
#
#                 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_A2D4

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
DW-3-8 (3-pyridyl)-CONH-(CH2)4-NHCO-(3-pyridyl), I-(CF2)4-I
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         
;
(C14 H14 N4 O2) (C4 F8 I2)
;
_chemical_formula_sum            'C18 H14 F8 I2 N4 O2'
_chemical_formula_weight         724.13

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

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

_cell_length_a                   12.7557(6)
_cell_length_b                   9.5667(5)
_cell_length_c                   9.7394(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 110.9880(10)
_cell_angle_gamma                90.00
_cell_volume                     1109.65(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    8281
_cell_measurement_theta_min      2.73
_cell_measurement_theta_max      32.26

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.14
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.167
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             688
_exptl_absorpt_coefficient_mu    2.925
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4545
_exptl_absorpt_correction_T_max  0.6848
_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            11790
_diffrn_reflns_av_R_equivalents  0.0295
_diffrn_reflns_av_sigmaI/netI    0.0288
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.73
_diffrn_reflns_theta_max         31.51
_reflns_number_total             3403
_reflns_number_gt                3095
_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    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3403
_refine_ls_number_parameters     157
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0285
_refine_ls_R_factor_gt           0.0252
_refine_ls_wR_factor_ref         0.0631
_refine_ls_wR_factor_gt          0.0607
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_restrained_S_all      1.069
_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
I1 I 0.356046(12) 0.477673(17) 0.782787(17) 0.01865(6) Uani 1 1 d . . .
N11 N 0.24878(19) 0.5271(2) 0.9959(3) 0.0232(4) Uani 1 1 d . . .
C12 C 0.18940(19) 0.4119(2) 0.9977(3) 0.0180(4) Uani 1 1 d . . .
H12 H 0.1895 0.3372 0.9335 0.022 Uiso 1 1 calc R . .
C13 C 0.12754(17) 0.3966(2) 1.0892(2) 0.0136(4) Uani 1 1 d . . .
C14 C 0.1296(2) 0.5051(2) 1.1844(3) 0.0170(4) Uani 1 1 d . . .
H14 H 0.0896 0.4977 1.2498 0.020 Uiso 1 1 calc R . .
C15 C 0.1905(2) 0.6242(3) 1.1830(3) 0.0199(4) Uani 1 1 d . . .
H15 H 0.1926 0.7003 1.2466 0.024 Uiso 1 1 calc R . .
C16 C 0.2483(2) 0.6304(3) 1.0872(3) 0.0227(5) Uani 1 1 d . . .
H16 H 0.2898 0.7126 1.0865 0.027 Uiso 1 1 calc R . .
C17 C 0.06139(17) 0.2680(2) 1.0893(2) 0.0137(4) Uani 1 1 d . . .
N17 N 0.03537(16) 0.1847(2) 0.9716(2) 0.0143(3) Uani 1 1 d . . .
H17 H 0.052(2) 0.209(3) 0.900(3) 0.017 Uiso 1 1 d . . .
O17 O 0.03070(15) 0.24151(18) 1.19343(18) 0.0201(3) Uani 1 1 d . . .
C21 C -0.03423(19) 0.0624(2) 0.9588(2) 0.0148(4) Uani 1 1 d . . .
H21A H -0.0712 0.0379 0.8536 0.018 Uiso 1 1 calc R . .
H21B H -0.0936 0.0839 0.9988 0.018 Uiso 1 1 calc R . .
C31 C 0.4091(2) 0.4115(3) 0.6072(3) 0.0255(5) Uani 1 1 d . . .
F31A F 0.4697(2) 0.29477(19) 0.6456(3) 0.0622(8) Uani 1 1 d . . .
F31B F 0.31751(19) 0.3822(3) 0.4879(2) 0.0581(7) Uani 1 1 d . . .
C32 C 0.47834(19) 0.5220(2) 0.5619(3) 0.0159(4) Uani 1 1 d . . .
F32A F 0.56648(13) 0.5571(2) 0.68085(17) 0.0291(3) Uani 1 1 d . . .
F32B F 0.41335(14) 0.63559(16) 0.51594(18) 0.0282(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
I1 C31 2.148(2) . ?
I1 N11 2.905(2) . ?
N11 C16 1.331(3) . ?
N11 C12 1.341(3) . ?
C12 C13 1.394(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.386(3) . ?
C13 C17 1.492(3) . ?
C14 C15 1.382(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.382(3) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 O17 1.237(2) . ?
C17 N17 1.337(3) . ?
N17 C21 1.447(3) . ?
N17 H17 0.83(3) . ?
C21 C21 1.526(4) 3_557 ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C31 F31A 1.333(3) . ?
C31 F31B 1.350(4) . ?
C31 C32 1.540(3) . ?
C32 F32A 1.336(3) . ?
C32 F32B 1.343(3) . ?
C32 C32 1.554(4) 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
C31 I1 N11 168.63(9) . . ?
C16 N11 C12 117.6(2) . . ?
C16 N11 I1 135.61(16) . . ?
C12 N11 I1 106.74(15) . . ?
N11 C12 C13 123.1(2) . . ?
N11 C12 H12 118.4 . . ?
C13 C12 H12 118.4 . . ?
C14 C13 C12 118.0(2) . . ?
C14 C13 C17 119.45(19) . . ?
C12 C13 C17 122.5(2) . . ?
C15 C14 C13 119.1(2) . . ?
C15 C14 H14 120.5 . . ?
C13 C14 H14 120.5 . . ?
C16 C15 C14 118.7(2) . . ?
C16 C15 H15 120.7 . . ?
C14 C15 H15 120.7 . . ?
N11 C16 C15 123.4(2) . . ?
N11 C16 H16 118.3 . . ?
C15 C16 H16 118.3 . . ?
O17 C17 N17 121.8(2) . . ?
O17 C17 C13 121.0(2) . . ?
N17 C17 C13 117.20(18) . . ?
C17 N17 C21 120.78(18) . . ?
C17 N17 H17 120(2) . . ?
C21 N17 H17 119(2) . . ?
N17 C21 C21 111.7(2) . 3_557 ?
N17 C21 H21A 109.3 . . ?
C21 C21 H21A 109.3 3_557 . ?
N17 C21 H21B 109.3 . . ?
C21 C21 H21B 109.3 3_557 . ?
H21A C21 H21B 107.9 . . ?
F31A C31 F31B 107.7(3) . . ?
F31A C31 C32 108.7(2) . . ?
F31B C31 C32 107.7(2) . . ?
F31A C31 I1 109.92(18) . . ?
F31B C31 I1 108.91(17) . . ?
C32 C31 I1 113.72(16) . . ?
F32A C32 F32B 108.25(19) . . ?
F32A C32 C31 108.3(2) . . ?
F32B C32 C31 107.61(19) . . ?
F32A C32 C32 108.5(2) . 3_666 ?
F32B C32 C32 108.0(2) . 3_666 ?
C31 C32 C32 115.9(2) . 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
C31 I1 N11 C16 -159.0(4) . . . . ?
C31 I1 N11 C12 22.8(5) . . . . ?
C16 N11 C12 C13 0.4(4) . . . . ?
I1 N11 C12 C13 179.03(19) . . . . ?
N11 C12 C13 C14 -1.2(4) . . . . ?
N11 C12 C13 C17 179.7(2) . . . . ?
C12 C13 C14 C15 1.2(3) . . . . ?
C17 C13 C14 C15 -179.6(2) . . . . ?
C13 C14 C15 C16 -0.6(4) . . . . ?
C12 N11 C16 C15 0.3(4) . . . . ?
I1 N11 C16 C15 -177.80(19) . . . . ?
C14 C15 C16 N11 -0.2(4) . . . . ?
C14 C13 C17 O17 -17.2(3) . . . . ?
C12 C13 C17 O17 161.9(2) . . . . ?
C14 C13 C17 N17 161.6(2) . . . . ?
C12 C13 C17 N17 -19.3(3) . . . . ?
O17 C17 N17 C21 2.6(3) . . . . ?
C13 C17 N17 C21 -176.27(19) . . . . ?
C17 N17 C21 C21 -83.3(3) . . . 3_557 ?
N11 I1 C31 F31A -82.7(5) . . . . ?
N11 I1 C31 F31B 35.1(6) . . . . ?
N11 I1 C31 C32 155.1(4) . . . . ?
F31A C31 C32 F32A -66.6(3) . . . . ?
F31B C31 C32 F32A 177.0(2) . . . . ?
I1 C31 C32 F32A 56.2(2) . . . . ?
F31A C31 C32 F32B 176.6(2) . . . . ?
F31B C31 C32 F32B 60.2(3) . . . . ?
I1 C31 C32 F32B -60.6(2) . . . . ?
F31A C31 C32 C32 55.6(3) . . . 3_666 ?
F31B C31 C32 C32 -60.8(3) . . . 3_666 ?
I1 C31 C32 C32 178.4(2) . . . 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
N17 H17 O17 0.83(3) 1.99(3) 2.779(2) 159(3) 4_565

_diffrn_measured_fraction_theta_max 0.922
_diffrn_reflns_theta_full        27.50
_diffrn_measured_fraction_theta_full 0.984
_refine_diff_density_max         0.721
_refine_diff_density_min         -0.805
_refine_diff_density_rms         0.118
_database_code_depnum_ccdc_archive 'CCDC 1011557'
#######################################################################
#
#                 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_A2D6

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
DW-3-9 (3-pyridyl)-CONH-(CH2)2-NHCO-(3-pyridyl), I-(CF2)6-I
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         
;
(C14 H14 N4 O2) (C6 F12 I2)
;
_chemical_formula_sum            'C20 H14 F12 I2 N4 O2'
_chemical_formula_weight         824.15

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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

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

_cell_length_a                   13.7352(8)
_cell_length_b                   9.3958(5)
_cell_length_c                   9.8519(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 103.888(2)
_cell_angle_gamma                90.00
_cell_volume                     1234.25(12)
_cell_formula_units_Z            2
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    9895
_cell_measurement_theta_min      2.65
_cell_measurement_theta_max      34.33

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.218
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             784
_exptl_absorpt_coefficient_mu    2.667
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4641
_exptl_absorpt_correction_T_max  0.7402
_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            20293
_diffrn_reflns_av_R_equivalents  0.0266
_diffrn_reflns_av_sigmaI/netI    0.0228
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.53
_diffrn_reflns_theta_max         34.39
_reflns_number_total             4958
_reflns_number_gt                4517
_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    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4958
_refine_ls_number_parameters     184
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0242
_refine_ls_R_factor_gt           0.0211
_refine_ls_wR_factor_ref         0.0484
_refine_ls_wR_factor_gt          0.0472
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_restrained_S_all      1.034
_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 0.22871(10) 0.47113(13) 0.19249(14) 0.0207(2) Uani 1 1 d . . .
C12 C 0.17257(10) 0.58535(14) 0.14533(14) 0.0166(2) Uani 1 1 d . . .
H12 H 0.1711 0.6611 0.2087 0.020 Uiso 1 1 calc R . .
C13 C 0.11619(9) 0.59886(14) 0.00829(13) 0.0131(2) Uani 1 1 d . . .
C14 C 0.11895(11) 0.48796(14) -0.08397(15) 0.0163(2) Uani 1 1 d . . .
H14 H 0.0817 0.4934 -0.1785 0.020 Uiso 1 1 calc R . .
C15 C 0.17671(11) 0.36965(15) -0.03613(16) 0.0193(3) Uani 1 1 d . . .
H15 H 0.1795 0.2922 -0.0970 0.023 Uiso 1 1 calc R . .
C16 C 0.23043(11) 0.36585(15) 0.10198(16) 0.0212(3) Uani 1 1 d . . .
H16 H 0.2704 0.2845 0.1339 0.025 Uiso 1 1 calc R . .
C17 C 0.05499(9) 0.72806(13) -0.04281(13) 0.0129(2) Uani 1 1 d . . .
N17 N 0.03089(8) 0.81155(12) 0.05374(12) 0.01317(19) Uani 1 1 d . . .
H17 H 0.0415(13) 0.785(2) 0.1343(19) 0.016 Uiso 1 1 d . . .
O17 O 0.02814(8) 0.75549(11) -0.16906(10) 0.0193(2) Uani 1 1 d . . .
C21 C -0.03107(10) 0.93669(14) 0.01424(14) 0.0142(2) Uani 1 1 d . . .
H21A H -0.0639 0.9614 0.0903 0.017 Uiso 1 1 calc R . .
H21B H -0.0843 0.9156 -0.0707 0.017 Uiso 1 1 calc R . .
C31 C 0.35070(11) 0.58641(16) 0.69834(15) 0.0191(3) Uani 1 1 d . . .
I1 I 0.318053(6) 0.521723(10) 0.483167(9) 0.01679(3) Uani 1 1 d . . .
F31A F 0.26630(7) 0.57239(16) 0.74422(11) 0.0368(3) Uani 1 1 d . . .
F31B F 0.37593(9) 0.72378(10) 0.71080(10) 0.0325(2) Uani 1 1 d . . .
C32 C 0.43439(11) 0.49847(15) 0.79439(16) 0.0168(2) Uani 1 1 d . . .
F32A F 0.40235(9) 0.36419(10) 0.79288(10) 0.0353(3) Uani 1 1 d . . .
F32B F 0.51506(8) 0.50239(14) 0.74165(12) 0.0343(3) Uani 1 1 d . . .
C33 C 0.46646(10) 0.55215(15) 0.94805(15) 0.0163(2) Uani 1 1 d . . .
F33A F 0.38457(7) 0.57949(12) 0.99461(10) 0.0266(2) Uani 1 1 d . . .
F33B F 0.51699(8) 0.67418(10) 0.94724(10) 0.0296(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 C16 1.336(2) . ?
N11 C12 1.3380(18) . ?
N11 I1 2.8716(13) . ?
C12 C13 1.3916(18) . ?
C12 H12 0.9500 . ?
C13 C14 1.3892(18) . ?
C13 C17 1.4934(18) . ?
C14 C15 1.3811(19) . ?
C14 H14 0.9500 . ?
C15 C16 1.384(2) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 O17 1.2366(16) . ?
C17 N17 1.3346(17) . ?
N17 C21 1.4488(17) . ?
N17 H17 0.811(18) . ?
C21 C21 1.529(3) 3_575 ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C31 F31B 1.3344(18) . ?
C31 F31A 1.3480(18) . ?
C31 C32 1.542(2) . ?
C31 I1 2.1466(15) . ?
C32 F32B 1.3325(18) . ?
C32 F32A 1.3351(16) . ?
C32 C33 1.556(2) . ?
C33 F33A 1.3376(17) . ?
C33 F33B 1.3412(16) . ?
C33 C33 1.551(3) 3_667 ?

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 117.60(13) . . ?
C16 N11 I1 135.77(10) . . ?
C12 N11 I1 106.63(9) . . ?
N11 C12 C13 123.38(13) . . ?
N11 C12 H12 118.3 . . ?
C13 C12 H12 118.3 . . ?
C14 C13 C12 118.04(12) . . ?
C14 C13 C17 119.39(12) . . ?
C12 C13 C17 122.57(12) . . ?
C15 C14 C13 118.95(13) . . ?
C15 C14 H14 120.5 . . ?
C13 C14 H14 120.5 . . ?
C14 C15 C16 118.90(13) . . ?
C14 C15 H15 120.5 . . ?
C16 C15 H15 120.5 . . ?
N11 C16 C15 123.13(13) . . ?
N11 C16 H16 118.4 . . ?
C15 C16 H16 118.4 . . ?
O17 C17 N17 121.95(12) . . ?
O17 C17 C13 121.08(12) . . ?
N17 C17 C13 116.96(11) . . ?
C17 N17 C21 121.06(11) . . ?
C17 N17 H17 120.0(13) . . ?
C21 N17 H17 118.0(13) . . ?
N17 C21 C21 111.28(13) . 3_575 ?
N17 C21 H21A 109.4 . . ?
C21 C21 H21A 109.4 3_575 . ?
N17 C21 H21B 109.4 . . ?
C21 C21 H21B 109.4 3_575 . ?
H21A C21 H21B 108.0 . . ?
F31B C31 F31A 106.79(13) . . ?
F31B C31 C32 108.84(12) . . ?
F31A C31 C32 108.44(12) . . ?
F31B C31 I1 110.66(10) . . ?
F31A C31 I1 108.11(10) . . ?
C32 C31 I1 113.74(10) . . ?
C31 I1 N11 165.86(5) . . ?
F32B C32 F32A 108.93(13) . . ?
F32B C32 C31 108.24(12) . . ?
F32A C32 C31 107.72(12) . . ?
F32B C32 C33 107.63(12) . . ?
F32A C32 C33 109.44(12) . . ?
C31 C32 C33 114.76(12) . . ?
F33A C33 F33B 108.47(12) . . ?
F33A C33 C33 108.08(15) . 3_667 ?
F33B C33 C33 108.53(14) . 3_667 ?
F33A C33 C32 109.33(11) . . ?
F33B C33 C32 107.30(12) . . ?
C33 C33 C32 114.96(15) 3_667 . ?

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 0.4(2) . . . . ?
I1 N11 C12 C13 -179.09(11) . . . . ?
N11 C12 C13 C14 -0.3(2) . . . . ?
N11 C12 C13 C17 -179.21(13) . . . . ?
C12 C13 C14 C15 0.2(2) . . . . ?
C17 C13 C14 C15 179.24(13) . . . . ?
C13 C14 C15 C16 -0.4(2) . . . . ?
C12 N11 C16 C15 -0.5(2) . . . . ?
I1 N11 C16 C15 178.76(11) . . . . ?
C14 C15 C16 N11 0.5(2) . . . . ?
C14 C13 C17 O17 -18.7(2) . . . . ?
C12 C13 C17 O17 160.19(14) . . . . ?
C14 C13 C17 N17 161.19(13) . . . . ?
C12 C13 C17 N17 -19.87(19) . . . . ?
O17 C17 N17 C21 2.0(2) . . . . ?
C13 C17 N17 C21 -177.92(11) . . . . ?
C17 N17 C21 C21 -82.40(18) . . . 3_575 ?
F31B C31 I1 N11 -77.1(2) . . . . ?
F31A C31 I1 N11 39.5(3) . . . . ?
C32 C31 I1 N11 159.97(15) . . . . ?
C16 N11 I1 C31 -145.9(2) . . . . ?
C12 N11 I1 C31 33.4(2) . . . . ?
F31B C31 C32 F32B -69.57(15) . . . . ?
F31A C31 C32 F32B 174.62(13) . . . . ?
I1 C31 C32 F32B 54.31(14) . . . . ?
F31B C31 C32 F32A 172.79(13) . . . . ?
F31A C31 C32 F32A 56.97(16) . . . . ?
I1 C31 C32 F32A -63.34(14) . . . . ?
F31B C31 C32 C33 50.64(17) . . . . ?
F31A C31 C32 C33 -65.18(16) . . . . ?
I1 C31 C32 C33 174.51(9) . . . . ?
F32B C32 C33 F33A 166.53(12) . . . . ?
F32A C32 C33 F33A -75.23(15) . . . . ?
C31 C32 C33 F33A 45.98(16) . . . . ?
F32B C32 C33 F33B 49.09(15) . . . . ?
F32A C32 C33 F33B 167.33(12) . . . . ?
C31 C32 C33 F33B -71.46(15) . . . . ?
F32B C32 C33 C33 -71.73(18) . . . 3_667 ?
F32A C32 C33 C33 46.5(2) . . . 3_667 ?
C31 C32 C33 C33 167.72(15) . . . 3_667 ?

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
N17 H17 O17 0.811(18) 2.026(19) 2.8117(15) 163.2(18) 4_576

_diffrn_measured_fraction_theta_max 0.956
_diffrn_reflns_theta_full        32.50
_diffrn_measured_fraction_theta_full 0.989
_refine_diff_density_max         0.555
_refine_diff_density_min         -0.469
_refine_diff_density_rms         0.096
_database_code_depnum_ccdc_archive 'CCDC 1011558'
#######################################################################
#
#                 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        
;
DW-3-18 (3-pyridyl)-CONH-(CH2)2-NHCO-(3-pyridyl), I-(CF2)8-I
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         
;
(C14 H14 N4 O2) (C8 F16 I2)
;
_chemical_formula_sum            'C22 H14 F16 I2 N4 O2'
_chemical_formula_weight         924.17

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           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                   15.1894(18)
_cell_length_b                   9.3947(11)
_cell_length_c                   9.8668(11)
_cell_angle_alpha                90.00
_cell_angle_beta                 95.169(4)
_cell_angle_gamma                90.00
_cell_volume                     1402.3(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    9963
_cell_measurement_theta_min      2.55
_cell_measurement_theta_max      33.12

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.189
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             880
_exptl_absorpt_coefficient_mu    2.380
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4983
_exptl_absorpt_correction_T_max  0.6739
_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            21943
_diffrn_reflns_av_R_equivalents  0.0450
_diffrn_reflns_av_sigmaI/netI    0.0279
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.35
_diffrn_reflns_theta_max         33.12
_reflns_number_total             4814
_reflns_number_gt                4426
_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)+(0.0450P)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         4814
_refine_ls_number_parameters     211
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0335
_refine_ls_R_factor_gt           0.0300
_refine_ls_wR_factor_ref         0.1023
_refine_ls_wR_factor_gt          0.0897
_refine_ls_goodness_of_fit_ref   1.213
_refine_ls_restrained_S_all      1.213
_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 0.29705(19) 0.4703(3) 0.8592(3) 0.0286(5) Uani 1 1 d . . .
C12 C 0.34679(18) 0.5850(3) 0.8925(3) 0.0219(5) Uani 1 1 d . . .
H12 H 0.3477 0.6603 0.8285 0.026 Uiso 1 1 calc R . .
C13 C 0.39712(16) 0.5985(3) 1.0169(2) 0.0172(4) Uani 1 1 d . . .
C14 C 0.3955(2) 0.4873(3) 1.1097(3) 0.0214(5) Uani 1 1 d . . .
H14 H 0.4291 0.4927 1.1956 0.026 Uiso 1 1 calc R . .
C15 C 0.3443(2) 0.3686(3) 1.0753(3) 0.0261(5) Uani 1 1 d . . .
H15 H 0.3422 0.2913 1.1370 0.031 Uiso 1 1 calc R . .
C16 C 0.2964(2) 0.3647(3) 0.9499(3) 0.0280(5) Uani 1 1 d . . .
H16 H 0.2612 0.2831 0.9268 0.034 Uiso 1 1 calc R . .
C17 C 0.45075(16) 0.7279(2) 1.0549(2) 0.0173(4) Uani 1 1 d . . .
N17 N 0.47216(14) 0.8111(2) 0.95335(19) 0.0179(4) Uani 1 1 d . . .
H17 H 0.461(2) 0.788(4) 0.872(4) 0.021 Uiso 1 1 d . . .
O17 O 0.47483(14) 0.7553(2) 1.17530(18) 0.0255(4) Uani 1 1 d . . .
C21 C 0.52711(17) 0.9364(3) 0.9794(2) 0.0184(4) Uani 1 1 d . . .
H21A H 0.5560 0.9607 0.8964 0.022 Uiso 1 1 calc R . .
H21B H 0.5740 0.9153 1.0529 0.022 Uiso 1 1 calc R . .
C31 C 0.19026(18) 0.5788(3) 0.3796(3) 0.0260(5) Uani 1 1 d . . .
I1 I 0.217210(12) 0.51564(2) 0.588276(16) 0.02371(7) Uani 1 1 d . . .
F31A F 0.26206(14) 0.5513(4) 0.3147(2) 0.0562(7) Uani 1 1 d . . .
F31B F 0.17699(17) 0.7196(2) 0.3721(2) 0.0468(6) Uani 1 1 d . . .
C32 C 0.1100(2) 0.5042(3) 0.3030(3) 0.0264(6) Uani 1 1 d . . .
F32A F 0.1285(2) 0.3657(2) 0.2977(2) 0.0599(8) Uani 1 1 d . . .
F32B F 0.04081(16) 0.5227(3) 0.3751(2) 0.0580(8) Uani 1 1 d . . .
C33 C 0.08432(18) 0.5602(3) 0.1571(3) 0.0232(5) Uani 1 1 d . . .
F33A F 0.15698(15) 0.5723(4) 0.0923(2) 0.0547(7) Uani 1 1 d . . .
F33B F 0.05054(18) 0.6904(2) 0.1671(2) 0.0540(7) Uani 1 1 d . . .
C34 C 0.0170(2) 0.4676(3) 0.0697(3) 0.0289(6) Uani 1 1 d . . .
F34A F 0.0571(2) 0.3451(3) 0.0469(3) 0.0803(11) Uani 1 1 d . . .
F34B F -0.05099(19) 0.4418(4) 0.1392(2) 0.0774(11) 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 1.336(4) . ?
N11 C12 1.340(3) . ?
N11 I1 2.866(3) . ?
C12 C13 1.392(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.392(3) . ?
C13 C17 1.492(3) . ?
C14 C15 1.384(4) . ?
C14 H14 0.9500 . ?
C15 C16 1.379(4) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 O17 1.238(3) . ?
C17 N17 1.334(3) . ?
N17 C21 1.452(3) . ?
N17 H17 0.84(4) . ?
C21 C21 1.527(5) 3_677 ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C31 F31A 1.338(4) . ?
C31 F31B 1.340(4) . ?
C31 C32 1.543(4) . ?
C31 I1 2.147(3) . ?
C32 F32B 1.333(4) . ?
C32 F32A 1.333(4) . ?
C32 C33 1.549(4) . ?
C33 F33A 1.330(3) . ?
C33 F33B 1.333(3) . ?
C33 C34 1.545(4) . ?
C34 F34B 1.313(4) . ?
C34 F34A 1.331(4) . ?
C34 C34 1.550(6) 3_565 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C16 N11 C12 118.1(3) . . ?
C16 N11 I1 134.98(19) . . ?
C12 N11 I1 106.95(18) . . ?
N11 C12 C13 122.9(2) . . ?
N11 C12 H12 118.6 . . ?
C13 C12 H12 118.6 . . ?
C14 C13 C12 118.1(2) . . ?
C14 C13 C17 119.2(2) . . ?
C12 C13 C17 122.7(2) . . ?
C15 C14 C13 119.1(3) . . ?
C15 C14 H14 120.4 . . ?
C13 C14 H14 120.4 . . ?
C16 C15 C14 118.8(3) . . ?
C16 C15 H15 120.6 . . ?
C14 C15 H15 120.6 . . ?
N11 C16 C15 123.1(3) . . ?
N11 C16 H16 118.4 . . ?
C15 C16 H16 118.4 . . ?
O17 C17 N17 121.9(2) . . ?
O17 C17 C13 121.2(2) . . ?
N17 C17 C13 116.9(2) . . ?
C17 N17 C21 121.15(19) . . ?
C17 N17 H17 122(2) . . ?
C21 N17 H17 116(2) . . ?
N17 C21 C21 111.5(3) . 3_677 ?
N17 C21 H21A 109.3 . . ?
C21 C21 H21A 109.3 3_677 . ?
N17 C21 H21B 109.3 . . ?
C21 C21 H21B 109.3 3_677 . ?
H21A C21 H21B 108.0 . . ?
F31A C31 F31B 106.8(3) . . ?
F31A C31 C32 108.7(2) . . ?
F31B C31 C32 108.2(2) . . ?
F31A C31 I1 108.21(19) . . ?
F31B C31 I1 109.89(18) . . ?
C32 C31 I1 114.7(2) . . ?
C31 I1 N11 164.56(9) . . ?
F32B C32 F32A 109.1(3) . . ?
F32B C32 C31 107.8(2) . . ?
F32A C32 C31 107.6(3) . . ?
F32B C32 C33 107.9(3) . . ?
F32A C32 C33 109.3(2) . . ?
C31 C32 C33 115.0(2) . . ?
F33A C33 F33B 107.4(3) . . ?
F33A C33 C34 108.4(2) . . ?
F33B C33 C34 108.5(2) . . ?
F33A C33 C32 109.0(2) . . ?
F33B C33 C32 108.0(2) . . ?
C34 C33 C32 115.2(2) . . ?
F34B C34 F34A 108.8(3) . . ?
F34B C34 C33 108.9(3) . . ?
F34A C34 C33 106.9(3) . . ?
F34B C34 C34 108.7(4) . 3_565 ?
F34A C34 C34 108.1(3) . 3_565 ?
C33 C34 C34 115.2(3) . 3_565 ?

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 -0.2(5) . . . . ?
I1 N11 C12 C13 -178.6(2) . . . . ?
N11 C12 C13 C14 0.2(4) . . . . ?
N11 C12 C13 C17 -178.5(3) . . . . ?
C12 C13 C14 C15 -0.1(4) . . . . ?
C17 C13 C14 C15 178.7(2) . . . . ?
C13 C14 C15 C16 -0.1(4) . . . . ?
C12 N11 C16 C15 0.0(5) . . . . ?
I1 N11 C16 C15 177.9(2) . . . . ?
C14 C15 C16 N11 0.1(5) . . . . ?
C14 C13 C17 O17 -18.7(4) . . . . ?
C12 C13 C17 O17 160.0(3) . . . . ?
C14 C13 C17 N17 160.5(2) . . . . ?
C12 C13 C17 N17 -20.7(4) . . . . ?
O17 C17 N17 C21 1.7(4) . . . . ?
C13 C17 N17 C21 -177.5(2) . . . . ?
C17 N17 C21 C21 -82.4(3) . . . 3_677 ?
F31A C31 I1 N11 45.1(5) . . . . ?
F31B C31 I1 N11 -71.1(4) . . . . ?
C32 C31 I1 N11 166.7(3) . . . . ?
C16 N11 I1 C31 -144.7(4) . . . . ?
C12 N11 I1 C31 33.3(5) . . . . ?
F31A C31 C32 F32B 174.9(3) . . . . ?
F31B C31 C32 F32B -69.5(3) . . . . ?
I1 C31 C32 F32B 53.6(3) . . . . ?
F31A C31 C32 F32A 57.4(3) . . . . ?
F31B C31 C32 F32A 173.0(3) . . . . ?
I1 C31 C32 F32A -63.9(3) . . . . ?
F31A C31 C32 C33 -64.7(4) . . . . ?
F31B C31 C32 C33 50.9(3) . . . . ?
I1 C31 C32 C33 174.0(2) . . . . ?
F32B C32 C33 F33A 166.4(3) . . . . ?
F32A C32 C33 F33A -75.1(3) . . . . ?
C31 C32 C33 F33A 46.1(4) . . . . ?
F32B C32 C33 F33B 50.1(3) . . . . ?
F32A C32 C33 F33B 168.5(3) . . . . ?
C31 C32 C33 F33B -70.3(3) . . . . ?
F32B C32 C33 C34 -71.5(3) . . . . ?
F32A C32 C33 C34 47.0(4) . . . . ?
C31 C32 C33 C34 168.2(3) . . . . ?
F33A C33 C34 F34B 173.1(3) . . . . ?
F33B C33 C34 F34B -70.6(3) . . . . ?
C32 C33 C34 F34B 50.7(4) . . . . ?
F33A C33 C34 F34A 55.7(3) . . . . ?
F33B C33 C34 F34A 172.0(3) . . . . ?
C32 C33 C34 F34A -66.7(4) . . . . ?
F33A C33 C34 C34 -64.5(4) . . . 3_565 ?
F33B C33 C34 C34 51.9(5) . . . 3_565 ?
C32 C33 C34 C34 173.1(3) . . . 3_565 ?

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
N17 H17 O17 0.84(4) 2.01(4) 2.817(3) 162(3) 4_575

_diffrn_measured_fraction_theta_max 0.901
_diffrn_reflns_theta_full        30.00
_diffrn_measured_fraction_theta_full 0.976
_refine_diff_density_max         0.841
_refine_diff_density_min         -0.899
_refine_diff_density_rms         0.155

#END

_database_code_depnum_ccdc_archive 'CCDC 1011559'
