# Electronic Supplementary Material for CrystEngComm
# This journal is (c) The Royal Society of Chemistry 2008

data_global

_journal_coden_Cambridge         1350

loop_
_publ_author_name
'C Aakeroy'

_publ_contact_author_name        'C Aakeroy'
_publ_contact_author_email       AAKEROY@KSU.EDU

_publ_section_title              
;
Ten years of co-crystal synthesis; The Good, the Bad,
and the Ugly
;

# Attachment 'Xray.cif'

data_A1
_database_code_depnum_ccdc_archive 'CCDC 694671'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
bis[N-(3-pyridyl)acetamide], 1,4-diiodotetrafluorobenzene
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         
;
(C7 H8 N2 O)2 (C6 F4 I2)
;
_chemical_formula_sum            'C20 H16 F4 I2 N4 O2'
_chemical_formula_weight         674.17

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)/n

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

_cell_length_a                   4.2616(9)
_cell_length_b                   29.232(6)
_cell_length_c                   17.734(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.860(4)
_cell_angle_gamma                90.00
_cell_volume                     2209.0(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    4784
_cell_measurement_theta_min      2.35
_cell_measurement_theta_max      28.00

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.03
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.027
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1288
_exptl_absorpt_coefficient_mu    2.906
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.603
_exptl_absorpt_correction_T_max  1.000
_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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            12189
_diffrn_reflns_av_R_equivalents  0.0319
_diffrn_reflns_av_sigmaI/netI    0.0436
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -37
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         1.15
_diffrn_reflns_theta_max         28.22
_reflns_number_total             4939
_reflns_number_gt                4460
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker XSCANS'
_computing_cell_refinement       'Bruker XSCANS'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_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+20.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4939
_refine_ls_number_parameters     298
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0651
_refine_ls_R_factor_gt           0.0578
_refine_ls_wR_factor_ref         0.1303
_refine_ls_wR_factor_gt          0.1255
_refine_ls_goodness_of_fit_ref   1.150
_refine_ls_restrained_S_all      1.150
_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 0.69214(11) 0.604682(16) 0.54169(2) 0.01893(13) Uani 1 1 d . . .
I2 I 0.03794(11) 0.472112(15) 0.83032(2) 0.01676(13) Uani 1 1 d . . .
N11 N 0.9186(15) 0.6524(2) 0.4163(3) 0.0220(13) Uani 1 1 d . . .
C12 C 0.7555(18) 0.6883(3) 0.3896(4) 0.0218(15) Uani 1 1 d . . .
H12 H 0.6387 0.7062 0.4241 0.026 Uiso 1 1 calc R . .
C13 C 0.7493(17) 0.7007(2) 0.3138(4) 0.0167(14) Uani 1 1 d . . .
N13 N 0.5659(15) 0.7360(2) 0.2835(3) 0.0188(12) Uani 1 1 d . . .
H13 H 0.52(2) 0.737(3) 0.238(5) 0.023 Uiso 1 1 d . . .
C14 C 0.9254(18) 0.6744(3) 0.2639(4) 0.0229(16) Uani 1 1 d . . .
H14 H 0.9277 0.6815 0.2117 0.027 Uiso 1 1 calc R . .
C15 C 1.0963(18) 0.6376(2) 0.2919(4) 0.0230(16) Uani 1 1 d . . .
H15 H 1.2192 0.6195 0.2592 0.028 Uiso 1 1 calc R . .
C16 C 1.0860(18) 0.6276(2) 0.3677(4) 0.0206(15) Uani 1 1 d . . .
H16 H 1.2023 0.6022 0.3863 0.025 Uiso 1 1 calc R . .
C17 C 0.4310(17) 0.7716(2) 0.3211(4) 0.0192(14) Uani 1 1 d . . .
O17 O 0.4659(14) 0.77714(19) 0.3899(3) 0.0279(13) Uani 1 1 d . . .
C18 C 0.2371(19) 0.8038(3) 0.2736(4) 0.0230(16) Uani 1 1 d . . .
H18A H 0.0372 0.8097 0.2984 0.035 Uiso 1 1 calc R . .
H18B H 0.1967 0.7900 0.2240 0.035 Uiso 1 1 calc R . .
H18C H 0.3509 0.8326 0.2673 0.035 Uiso 1 1 calc R . .
N21 N -0.2339(15) 0.4188(2) 0.9434(3) 0.0192(13) Uani 1 1 d . . .
C22 C -0.3228(18) 0.3750(2) 0.9360(4) 0.0210(15) Uani 1 1 d . . .
H22 H -0.2548 0.3584 0.8932 0.025 Uiso 1 1 calc R . .
C23 C -0.5091(18) 0.3527(2) 0.9879(4) 0.0185(14) Uani 1 1 d . . .
N23 N -0.6074(15) 0.3072(2) 0.9831(3) 0.0201(13) Uani 1 1 d . . .
H23 H -0.71(2) 0.298(3) 1.019(5) 0.024 Uiso 1 1 d . . .
C24 C -0.6072(18) 0.3781(2) 1.0506(4) 0.0199(15) Uani 1 1 d . . .
H24 H -0.7355 0.3643 1.0876 0.024 Uiso 1 1 calc R . .
C25 C -0.5169(18) 0.4228(2) 1.0582(4) 0.0207(15) Uani 1 1 d . . .
H25 H -0.5816 0.4403 1.1003 0.025 Uiso 1 1 calc R . .
C26 C -0.3293(19) 0.4421(3) 1.0034(4) 0.0226(15) Uani 1 1 d . . .
H26 H -0.2664 0.4731 1.0088 0.027 Uiso 1 1 calc R . .
C27 C -0.5595(18) 0.2771(2) 0.9275(4) 0.0193(14) Uani 1 1 d . . .
O27 O -0.4112(13) 0.28588(17) 0.8699(3) 0.0234(11) Uani 1 1 d . . .
C28 C -0.708(2) 0.2304(3) 0.9380(4) 0.0258(17) Uani 1 1 d . . .
H28A H -0.6059 0.2082 0.9051 0.039 Uiso 1 1 calc R . .
H28B H -0.9321 0.2321 0.9251 0.039 Uiso 1 1 calc R . .
H28C H -0.6819 0.2208 0.9907 0.039 Uiso 1 1 calc R . .
C31 C 0.4987(17) 0.5655(3) 0.6283(4) 0.0183(14) Uani 1 1 d . . .
C32 C 0.3276(18) 0.5854(2) 0.6859(4) 0.0187(14) Uani 1 1 d . . .
F32 F 0.2888(11) 0.63145(14) 0.6878(2) 0.0230(9) Uani 1 1 d . . .
C33 C 0.1944(16) 0.5595(2) 0.7419(4) 0.0162(14) Uani 1 1 d . . .
F33 F 0.0302(11) 0.58132(15) 0.7957(2) 0.0253(10) Uani 1 1 d . . .
C34 C 0.2267(17) 0.5125(2) 0.7438(4) 0.0161(13) Uani 1 1 d . . .
C35 C 0.3908(17) 0.4924(2) 0.6873(4) 0.0177(14) Uani 1 1 d . . .
F35 F 0.4304(11) 0.44675(14) 0.6841(2) 0.0237(9) Uani 1 1 d . . .
C36 C 0.5273(17) 0.5184(2) 0.6299(4) 0.0179(14) Uani 1 1 d . . .
F36 F 0.6936(11) 0.49652(15) 0.5769(2) 0.0251(10) 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 2.095(7) . ?
I2 C34 2.106(6) . ?
N11 C16 1.340(9) . ?
N11 C12 1.341(10) . ?
C12 C13 1.393(9) . ?
C12 H12 0.9500 . ?
C13 N13 1.397(9) . ?
C13 C14 1.399(10) . ?
N13 C17 1.365(9) . ?
N13 H13 0.83(9) . ?
C14 C15 1.386(11) . ?
C14 H14 0.9500 . ?
C15 C16 1.376(10) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 O17 1.239(9) . ?
C17 C18 1.502(10) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
N21 C26 1.332(9) . ?
N21 C22 1.341(9) . ?
C22 C23 1.386(10) . ?
C22 H22 0.9500 . ?
C23 N23 1.395(9) . ?
C23 C24 1.407(9) . ?
N23 C27 1.341(9) . ?
N23 H23 0.83(9) . ?
C24 C25 1.368(10) . ?
C24 H24 0.9500 . ?
C25 C26 1.388(10) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?
C27 O27 1.237(8) . ?
C27 C28 1.516(10) . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?
C31 C36 1.384(10) . ?
C31 C32 1.391(10) . ?
C32 F32 1.356(8) . ?
C32 C33 1.377(9) . ?
C33 F33 1.351(7) . ?
C33 C34 1.381(10) . ?
C34 C35 1.364(9) . ?
C35 F35 1.348(8) . ?
C35 C36 1.402(9) . ?
C36 F36 1.346(7) . ?

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 118.4(6) . . ?
N11 C12 C13 123.1(7) . . ?
N11 C12 H12 118.5 . . ?
C13 C12 H12 118.5 . . ?
C12 C13 N13 124.4(6) . . ?
C12 C13 C14 117.6(7) . . ?
N13 C13 C14 117.8(6) . . ?
C17 N13 C13 127.8(6) . . ?
C17 N13 H13 110(6) . . ?
C13 N13 H13 122(6) . . ?
C15 C14 C13 119.0(7) . . ?
C15 C14 H14 120.5 . . ?
C13 C14 H14 120.5 . . ?
C16 C15 C14 119.3(7) . . ?
C16 C15 H15 120.3 . . ?
C14 C15 H15 120.3 . . ?
N11 C16 C15 122.6(7) . . ?
N11 C16 H16 118.7 . . ?
C15 C16 H16 118.7 . . ?
O17 C17 N13 122.4(7) . . ?
O17 C17 C18 121.8(7) . . ?
N13 C17 C18 115.8(6) . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C26 N21 C22 118.4(6) . . ?
N21 C22 C23 123.3(6) . . ?
N21 C22 H22 118.4 . . ?
C23 C22 H22 118.4 . . ?
C22 C23 N23 125.6(6) . . ?
C22 C23 C24 117.2(6) . . ?
N23 C23 C24 117.2(6) . . ?
C27 N23 C23 128.4(6) . . ?
C27 N23 H23 116(6) . . ?
C23 N23 H23 116(6) . . ?
C25 C24 C23 119.7(6) . . ?
C25 C24 H24 120.2 . . ?
C23 C24 H24 120.2 . . ?
C24 C25 C26 118.9(6) . . ?
C24 C25 H25 120.5 . . ?
C26 C25 H25 120.5 . . ?
N21 C26 C25 122.6(7) . . ?
N21 C26 H26 118.7 . . ?
C25 C26 H26 118.7 . . ?
O27 C27 N23 123.8(7) . . ?
O27 C27 C28 120.6(6) . . ?
N23 C27 C28 115.7(6) . . ?
C27 C28 H28A 109.5 . . ?
C27 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
C27 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C36 C31 C32 116.7(6) . . ?
C36 C31 I1 121.6(5) . . ?
C32 C31 I1 121.7(5) . . ?
F32 C32 C33 118.4(6) . . ?
F32 C32 C31 119.9(6) . . ?
C33 C32 C31 121.7(7) . . ?
F33 C33 C32 118.3(6) . . ?
F33 C33 C34 120.2(6) . . ?
C32 C33 C34 121.5(6) . . ?
C35 C34 C33 117.5(6) . . ?
C35 C34 I2 120.0(5) . . ?
C33 C34 I2 122.5(5) . . ?
F35 C35 C34 121.5(6) . . ?
F35 C35 C36 116.9(6) . . ?
C34 C35 C36 121.6(6) . . ?
F36 C36 C31 120.4(6) . . ?
F36 C36 C35 118.6(6) . . ?
C31 C36 C35 121.0(6) . . ?

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 0.8(12) . . . . ?
N11 C12 C13 N13 175.6(7) . . . . ?
N11 C12 C13 C14 -0.7(12) . . . . ?
C12 C13 N13 C17 18.9(12) . . . . ?
C14 C13 N13 C17 -164.9(7) . . . . ?
C12 C13 C14 C15 -0.1(11) . . . . ?
N13 C13 C14 C15 -176.6(7) . . . . ?
C13 C14 C15 C16 0.7(12) . . . . ?
C12 N11 C16 C15 -0.1(12) . . . . ?
C14 C15 C16 N11 -0.6(12) . . . . ?
C13 N13 C17 O17 2.0(12) . . . . ?
C13 N13 C17 C18 -178.2(7) . . . . ?
C26 N21 C22 C23 0.0(11) . . . . ?
N21 C22 C23 N23 -179.8(7) . . . . ?
N21 C22 C23 C24 0.2(12) . . . . ?
C22 C23 N23 C27 -3.9(13) . . . . ?
C24 C23 N23 C27 176.2(8) . . . . ?
C22 C23 C24 C25 -0.1(11) . . . . ?
N23 C23 C24 C25 179.8(7) . . . . ?
C23 C24 C25 C26 0.0(11) . . . . ?
C22 N21 C26 C25 -0.2(11) . . . . ?
C24 C25 C26 N21 0.2(12) . . . . ?
C23 N23 C27 O27 0.5(13) . . . . ?
C23 N23 C27 C28 -177.8(7) . . . . ?
C36 C31 C32 F32 -179.8(6) . . . . ?
I1 C31 C32 F32 -1.5(10) . . . . ?
C36 C31 C32 C33 0.3(11) . . . . ?
I1 C31 C32 C33 178.5(6) . . . . ?
F32 C32 C33 F33 0.4(10) . . . . ?
C31 C32 C33 F33 -179.7(7) . . . . ?
F32 C32 C33 C34 -179.4(7) . . . . ?
C31 C32 C33 C34 0.6(11) . . . . ?
F33 C33 C34 C35 179.0(7) . . . . ?
C32 C33 C34 C35 -1.3(11) . . . . ?
F33 C33 C34 I2 -1.6(10) . . . . ?
C32 C33 C34 I2 178.1(6) . . . . ?
C33 C34 C35 F35 -179.1(7) . . . . ?
I2 C34 C35 F35 1.5(10) . . . . ?
C33 C34 C35 C36 1.2(11) . . . . ?
I2 C34 C35 C36 -178.2(6) . . . . ?
C32 C31 C36 F36 -178.9(6) . . . . ?
I1 C31 C36 F36 2.9(10) . . . . ?
C32 C31 C36 C35 -0.4(11) . . . . ?
I1 C31 C36 C35 -178.6(5) . . . . ?
F35 C35 C36 F36 -1.6(10) . . . . ?
C34 C35 C36 F36 178.2(7) . . . . ?
F35 C35 C36 C31 179.9(7) . . . . ?
C34 C35 C36 C31 -0.4(11) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N13 H13 O27 0.83(9) 2.07(9) 2.862(8) 159(8) 3_566
N23 H23 O17 0.83(9) 2.05(9) 2.877(8) 178(8) 2_446

_diffrn_measured_fraction_theta_max 0.905
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.992
_refine_diff_density_max         2.264
_refine_diff_density_min         -1.944
_refine_diff_density_rms         0.199

#END

data_A2
_database_code_depnum_ccdc_archive 'CCDC 694672'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
bis{N-[(3-pyridyl)methyl]acetamide}, 1,4-diiodotetrafluorobenzene
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         
;
(C8 H10 N2 O)2 (C6 F4 I2)
;
_chemical_formula_sum            'C22 H20 F4 I2 N4 O2'
_chemical_formula_weight         702.22

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                   4.845(2)
_cell_length_b                   9.716(4)
_cell_length_c                   13.075(6)
_cell_angle_alpha                104.096(6)
_cell_angle_beta                 98.360(6)
_cell_angle_gamma                91.246(6)
_cell_volume                     589.6(4)
_cell_formula_units_Z            1
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2387
_cell_measurement_theta_min      3.00
_cell_measurement_theta_max      27.15

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.02
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.978
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             338
_exptl_absorpt_coefficient_mu    2.726
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.515
_exptl_absorpt_correction_T_max  1.000
_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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5352
_diffrn_reflns_av_R_equivalents  0.0424
_diffrn_reflns_av_sigmaI/netI    0.0666
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.36
_diffrn_reflns_theta_max         27.21
_reflns_number_total             2580
_reflns_number_gt                2232
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker XSCANS'
_computing_cell_refinement       'Bruker XSCANS'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_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+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         2580
_refine_ls_number_parameters     155
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0649
_refine_ls_R_factor_gt           0.0535
_refine_ls_wR_factor_ref         0.1301
_refine_ls_wR_factor_gt          0.1245
_refine_ls_goodness_of_fit_ref   1.111
_refine_ls_restrained_S_all      1.111
_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
I2 I -0.06014(9) 0.22087(5) 0.40768(4) 0.01878(17) Uani 1 1 d . . .
N11 N 0.2831(13) 0.3728(7) 0.3122(5) 0.0252(14) Uani 1 1 d . . .
C12 C 0.4052(15) 0.5025(8) 0.3498(6) 0.0238(16) Uani 1 1 d . . .
H12 H 0.3688 0.5568 0.4169 0.029 Uiso 1 1 calc R . .
C13 C 0.5822(15) 0.5630(8) 0.2969(6) 0.0227(15) Uani 1 1 d . . .
H13 H 0.6661 0.6560 0.3275 0.027 Uiso 1 1 calc R . .
C14 C 0.6360(14) 0.4854(8) 0.1978(6) 0.0219(15) Uani 1 1 d . . .
C15 C 0.5138(15) 0.3478(8) 0.1581(6) 0.0241(16) Uani 1 1 d . . .
H15 H 0.5495 0.2898 0.0921 0.029 Uiso 1 1 calc R . .
C16 C 0.3373(16) 0.2976(9) 0.2184(6) 0.0271(17) Uani 1 1 d . . .
H16 H 0.2512 0.2046 0.1908 0.033 Uiso 1 1 calc R . .
C17 C 0.8247(15) 0.5452(8) 0.1340(6) 0.0255(16) Uani 1 1 d . . .
H17A H 1.0202 0.5550 0.1710 0.031 Uiso 1 1 calc R . .
H17B H 0.8171 0.4791 0.0627 0.031 Uiso 1 1 calc R . .
N17 N 0.7353(12) 0.6843(7) 0.1221(5) 0.0222(13) Uani 1 1 d . . .
H17 H 0.5638 0.7072 0.1304 0.027 Uiso 1 1 calc R . .
C18 C 0.9078(15) 0.7765(8) 0.0990(6) 0.0216(15) Uani 1 1 d . . .
O18 O 1.1508(10) 0.7515(6) 0.0851(4) 0.0257(12) Uani 1 1 d . . .
C19 C 0.7898(16) 0.9168(8) 0.0902(6) 0.0261(16) Uani 1 1 d . . .
H19A H 0.8242 0.9367 0.0230 0.039 Uiso 1 1 calc R . .
H19B H 0.8807 0.9929 0.1503 0.039 Uiso 1 1 calc R . .
H19C H 0.5882 0.9117 0.0915 0.039 Uiso 1 1 calc R . .
C21 C -0.3204(14) 0.0885(8) 0.4645(6) 0.0197(14) Uani 1 1 d . . .
C22 C -0.3161(14) 0.0963(8) 0.5714(6) 0.0199(14) Uani 1 1 d . . .
F22 F -0.1275(9) 0.1892(5) 0.6446(3) 0.0260(10) Uani 1 1 d . . .
C26 C -0.5107(14) -0.0110(8) 0.3933(6) 0.0198(14) Uani 1 1 d . . .
F26 F -0.5300(9) -0.0255(5) 0.2877(3) 0.0278(10) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I2 C21 2.113(6) . ?
N11 C12 1.327(10) . ?
N11 C16 1.332(11) . ?
C12 C13 1.382(10) . ?
C12 H12 0.9500 . ?
C13 C14 1.395(11) . ?
C13 H13 0.9500 . ?
C14 C15 1.395(11) . ?
C14 C17 1.518(9) . ?
C15 C16 1.397(10) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 N17 1.465(10) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
N17 C18 1.328(8) . ?
N17 H17 0.8800 . ?
C18 O18 1.238(9) . ?
C18 C19 1.513(11) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C21 C22 1.379(10) . ?
C21 C26 1.387(10) . ?
C22 F22 1.362(8) . ?
C22 C26 1.369(9) 2_456 ?
C26 F26 1.342(8) . ?
C26 C22 1.369(9) 2_456 ?

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 117.5(6) . . ?
N11 C12 C13 123.7(7) . . ?
N11 C12 H12 118.2 . . ?
C13 C12 H12 118.2 . . ?
C12 C13 C14 119.0(7) . . ?
C12 C13 H13 120.5 . . ?
C14 C13 H13 120.5 . . ?
C13 C14 C15 118.0(6) . . ?
C13 C14 C17 122.1(7) . . ?
C15 C14 C17 119.8(7) . . ?
C14 C15 C16 118.0(7) . . ?
C14 C15 H15 121.0 . . ?
C16 C15 H15 121.0 . . ?
N11 C16 C15 123.7(7) . . ?
N11 C16 H16 118.1 . . ?
C15 C16 H16 118.1 . . ?
N17 C17 C14 110.0(6) . . ?
N17 C17 H17A 109.7 . . ?
C14 C17 H17A 109.7 . . ?
N17 C17 H17B 109.7 . . ?
C14 C17 H17B 109.7 . . ?
H17A C17 H17B 108.2 . . ?
C18 N17 C17 121.3(6) . . ?
C18 N17 H17 119.3 . . ?
C17 N17 H17 119.3 . . ?
O18 C18 N17 123.2(7) . . ?
O18 C18 C19 120.9(6) . . ?
N17 C18 C19 115.9(6) . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C22 C21 C26 116.6(6) . . ?
C22 C21 I2 123.2(5) . . ?
C26 C21 I2 120.2(5) . . ?
F22 C22 C26 118.7(6) . 2_456 ?
F22 C22 C21 119.0(6) . . ?
C26 C22 C21 122.3(7) 2_456 . ?
F26 C26 C22 118.3(6) . 2_456 ?
F26 C26 C21 120.6(6) . . ?
C22 C26 C21 121.1(7) 2_456 . ?

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(11) . . . . ?
N11 C12 C13 C14 0.6(12) . . . . ?
C12 C13 C14 C15 -1.9(11) . . . . ?
C12 C13 C14 C17 179.1(7) . . . . ?
C13 C14 C15 C16 2.1(11) . . . . ?
C17 C14 C15 C16 -178.9(7) . . . . ?
C12 N11 C16 C15 -0.1(11) . . . . ?
C14 C15 C16 N11 -1.2(12) . . . . ?
C13 C14 C17 N17 -52.3(9) . . . . ?
C15 C14 C17 N17 128.8(7) . . . . ?
C14 C17 N17 C18 159.5(6) . . . . ?
C17 N17 C18 O18 0.8(11) . . . . ?
C17 N17 C18 C19 -179.4(6) . . . . ?
C26 C21 C22 F22 178.1(6) . . . . ?
I2 C21 C22 F22 -3.0(10) . . . . ?
C26 C21 C22 C26 0.1(12) . . . 2_456 ?
I2 C21 C22 C26 179.0(6) . . . 2_456 ?
C22 C21 C26 F26 179.8(7) . . . . ?
I2 C21 C26 F26 0.8(9) . . . . ?
C22 C21 C26 C22 -0.1(12) . . . 2_456 ?
I2 C21 C26 C22 -179.1(6) . . . 2_456 ?

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 O18 0.88 2.09 2.918(8) 157.1 1_455

_diffrn_measured_fraction_theta_max 0.977
_diffrn_reflns_theta_full        27.21
_diffrn_measured_fraction_theta_full 0.977
_refine_diff_density_max         2.064
_refine_diff_density_min         -2.006
_refine_diff_density_rms         0.238

#END

data_A3
_database_code_depnum_ccdc_archive 'CCDC 694673'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
4-(pyrazol-3-yl)pyridine, 1,4-diiodotetrafluorobenzene
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         
;
(C8 H7 N3) (C6 F4 I2)
;
_chemical_formula_sum            'C14 H7 F4 I2 N3'
_chemical_formula_weight         547.03

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

_symmetry_cell_setting           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                   7.1917(5)
_cell_length_b                   24.644(2)
_cell_length_c                   8.7269(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 100.535(5)
_cell_angle_gamma                90.00
_cell_volume                     1520.6(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    3135
_cell_measurement_theta_min      2.50
_cell_measurement_theta_max      28.20

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.389
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1016
_exptl_absorpt_coefficient_mu    4.180
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.694
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      173(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10619
_diffrn_reflns_av_R_equivalents  0.1174
_diffrn_reflns_av_sigmaI/netI    0.0800
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -32
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         1.65
_diffrn_reflns_theta_max         28.27
_reflns_number_total             3501
_reflns_number_gt                3003
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker XSCANS'
_computing_cell_refinement       'Bruker XSCANS'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_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)+(0.0900P)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     SHELXL
_refine_ls_extinction_coef       0.0149(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3501
_refine_ls_number_parameters     209
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0623
_refine_ls_R_factor_gt           0.0558
_refine_ls_wR_factor_ref         0.1415
_refine_ls_wR_factor_gt          0.1353
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_restrained_S_all      1.070
_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 0.37754(5) 0.138143(13) 0.48148(4) 0.02150(18) Uani 1 1 d . . .
I2 I 0.77326(6) 0.025027(18) 0.12028(4) 0.03516(19) Uani 1 1 d . . .
N11 N 0.4149(7) 0.2807(2) 0.4144(5) 0.0260(10) Uani 1 1 d . . .
H11 H 0.5010 0.2665 0.3667 0.031 Uiso 1 1 calc R . .
N12 N 0.2931(7) 0.25160(18) 0.4790(5) 0.0240(9) Uani 1 1 d . . .
C13 C 0.1873(8) 0.2880(2) 0.5386(5) 0.0208(10) Uani 1 1 d . . .
C14 C 0.2430(9) 0.3407(2) 0.5092(7) 0.0304(12) Uani 1 1 d . . .
H14 H 0.1905 0.3738 0.5372 0.036 Uiso 1 1 calc R . .
C15 C 0.3907(9) 0.3341(2) 0.4306(7) 0.0302(12) Uani 1 1 d . . .
H15 H 0.4622 0.3622 0.3946 0.036 Uiso 1 1 calc R . .
N21 N -0.2812(7) 0.2461(2) 0.7555(5) 0.0285(10) Uani 1 1 d . . .
C22 C -0.1675(9) 0.2078(3) 0.7126(7) 0.0305(12) Uani 1 1 d . . .
H22 H -0.1947 0.1709 0.7306 0.037 Uiso 1 1 calc R . .
C23 C -0.0137(8) 0.2192(2) 0.6441(6) 0.0250(11) Uani 1 1 d . . .
H23 H 0.0627 0.1905 0.6173 0.030 Uiso 1 1 calc R . .
C24 C 0.0292(7) 0.2727(2) 0.6143(5) 0.0211(10) Uani 1 1 d . . .
C25 C -0.0877(9) 0.3118(2) 0.6598(7) 0.0335(13) Uani 1 1 d . . .
H25 H -0.0632 0.3491 0.6445 0.040 Uiso 1 1 calc R . .
C26 C -0.2389(9) 0.2971(3) 0.7268(7) 0.0338(13) Uani 1 1 d . . .
H26 H -0.3178 0.3251 0.7542 0.041 Uiso 1 1 calc R . .
C31 C 0.4510(7) 0.0560(2) 0.4920(6) 0.0193(9) Uani 1 1 d . . .
C32 C 0.3979(7) 0.0214(2) 0.3671(6) 0.0210(10) Uani 1 1 d . . .
F32 F 0.2978(5) 0.04052(14) 0.2333(3) 0.0287(7) Uani 1 1 d . . .
C36 C 0.5537(7) 0.0325(2) 0.6264(6) 0.0201(10) Uani 1 1 d . . .
F36 F 0.6122(5) 0.06345(14) 0.7530(4) 0.0311(7) Uani 1 1 d . . .
C41 C 0.9077(8) 0.0105(2) 0.3468(6) 0.0255(11) Uani 1 1 d . . .
C42 C 0.9269(7) 0.0500(2) 0.4592(6) 0.0228(10) Uani 1 1 d . . .
F42 F 0.8567(5) 0.09975(13) 0.4254(4) 0.0333(8) Uani 1 1 d . . .
C46 C 0.9824(8) -0.0400(2) 0.3898(6) 0.0249(11) Uani 1 1 d . . .
F46 F 0.9708(6) -0.07998(14) 0.2859(4) 0.0365(8) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I1 C31 2.089(5) . ?
I2 C41 2.067(5) . ?
N11 N12 1.335(6) . ?
N11 C15 1.337(8) . ?
N11 H11 0.8800 . ?
N12 C13 1.341(7) . ?
C13 C14 1.396(7) . ?
C13 C24 1.464(7) . ?
C14 C15 1.375(8) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
N21 C26 1.329(8) . ?
N21 C22 1.345(8) . ?
C22 C23 1.379(7) . ?
C22 H22 0.9500 . ?
C23 C24 1.390(8) . ?
C23 H23 0.9500 . ?
C24 C25 1.385(8) . ?
C25 C26 1.375(8) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?
C31 C32 1.383(7) . ?
C31 C36 1.394(7) . ?
C32 F32 1.341(6) . ?
C32 C36 1.369(7) 3_656 ?
C36 F36 1.345(6) . ?
C36 C32 1.369(7) 3_656 ?
C41 C42 1.370(8) . ?
C41 C46 1.381(8) . ?
C42 F42 1.339(6) . ?
C42 C46 1.382(8) 3_756 ?
C46 F46 1.330(6) . ?
C46 C42 1.382(8) 3_756 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N12 N11 C15 112.1(4) . . ?
N12 N11 H11 124.0 . . ?
C15 N11 H11 124.0 . . ?
N11 N12 C13 105.5(4) . . ?
N12 C13 C14 110.4(4) . . ?
N12 C13 C24 123.0(5) . . ?
C14 C13 C24 126.5(5) . . ?
C15 C14 C13 104.8(5) . . ?
C15 C14 H14 127.6 . . ?
C13 C14 H14 127.6 . . ?
N11 C15 C14 107.3(5) . . ?
N11 C15 H15 126.4 . . ?
C14 C15 H15 126.4 . . ?
C26 N21 C22 116.1(5) . . ?
N21 C22 C23 123.7(6) . . ?
N21 C22 H22 118.2 . . ?
C23 C22 H22 118.2 . . ?
C22 C23 C24 119.8(5) . . ?
C22 C23 H23 120.1 . . ?
C24 C23 H23 120.1 . . ?
C25 C24 C23 116.1(5) . . ?
C25 C24 C13 120.8(5) . . ?
C23 C24 C13 123.1(5) . . ?
C26 C25 C24 120.5(6) . . ?
C26 C25 H25 119.7 . . ?
C24 C25 H25 119.7 . . ?
N21 C26 C25 123.7(5) . . ?
N21 C26 H26 118.1 . . ?
C25 C26 H26 118.1 . . ?
C32 C31 C36 115.6(5) . . ?
C32 C31 I1 122.2(4) . . ?
C36 C31 I1 122.1(4) . . ?
F32 C32 C36 118.0(4) . 3_656 ?
F32 C32 C31 119.7(5) . . ?
C36 C32 C31 122.3(5) 3_656 . ?
F36 C36 C32 118.5(5) . 3_656 ?
F36 C36 C31 119.5(4) . . ?
C32 C36 C31 122.0(5) 3_656 . ?
C42 C41 C46 117.6(5) . . ?
C42 C41 I2 122.0(4) . . ?
C46 C41 I2 120.4(4) . . ?
F42 C42 C41 120.6(5) . . ?
F42 C42 C46 117.7(5) . 3_756 ?
C41 C42 C46 121.7(5) . 3_756 ?
F46 C46 C41 120.6(5) . . ?
F46 C46 C42 118.6(5) . 3_756 ?
C41 C46 C42 120.7(5) . 3_756 ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C15 N11 N12 C13 0.0(6) . . . . ?
N11 N12 C13 C14 0.6(6) . . . . ?
N11 N12 C13 C24 177.1(5) . . . . ?
N12 C13 C14 C15 -1.0(7) . . . . ?
C24 C13 C14 C15 -177.3(5) . . . . ?
N12 N11 C15 C14 -0.6(6) . . . . ?
C13 C14 C15 N11 1.0(6) . . . . ?
C26 N21 C22 C23 0.6(9) . . . . ?
N21 C22 C23 C24 -0.7(9) . . . . ?
C22 C23 C24 C25 1.1(8) . . . . ?
C22 C23 C24 C13 -178.6(5) . . . . ?
N12 C13 C24 C25 -173.4(5) . . . . ?
C14 C13 C24 C25 2.5(9) . . . . ?
N12 C13 C24 C23 6.3(8) . . . . ?
C14 C13 C24 C23 -177.8(5) . . . . ?
C23 C24 C25 C26 -1.5(9) . . . . ?
C13 C24 C25 C26 178.2(6) . . . . ?
C22 N21 C26 C25 -1.0(9) . . . . ?
C24 C25 C26 N21 1.5(10) . . . . ?
C36 C31 C32 F32 179.6(4) . . . . ?
I1 C31 C32 F32 0.8(6) . . . . ?
C36 C31 C32 C36 -1.3(8) . . . 3_656 ?
I1 C31 C32 C36 179.8(4) . . . 3_656 ?
C32 C31 C36 F36 179.5(4) . . . . ?
I1 C31 C36 F36 -1.7(7) . . . . ?
C32 C31 C36 C32 1.3(8) . . . 3_656 ?
I1 C31 C36 C32 -179.8(4) . . . 3_656 ?
C46 C41 C42 F42 -179.6(4) . . . . ?
I2 C41 C42 F42 0.5(7) . . . . ?
C46 C41 C42 C46 0.1(9) . . . 3_756 ?
I2 C41 C42 C46 -179.7(4) . . . 3_756 ?
C42 C41 C46 F46 -179.2(5) . . . . ?
I2 C41 C46 F46 0.7(7) . . . . ?
C42 C41 C46 C42 -0.1(8) . . . 3_756 ?
I2 C41 C46 C42 179.7(4) . . . 3_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
N11 H11 N21 0.88 2.01 2.872(6) 165.3 4_665

_diffrn_measured_fraction_theta_max 0.927
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         2.207
_refine_diff_density_min         -1.208
_refine_diff_density_rms         0.350

#END

data_A4
_database_code_depnum_ccdc_archive 'CCDC 694674'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
2-(4-pyridyl)benzimidazole, 1,4-diiodotetrafluorobenzene, methanol
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         
;
(C12 H9 N3) (C6 F4 I2) (C H4 O)
;
_chemical_formula_sum            'C19 H13 F4 I2 N3 O'
_chemical_formula_weight         629.12

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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                   9.0808(7)
_cell_length_b                   16.3144(12)
_cell_length_c                   13.6934(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 91.057(4)
_cell_angle_gamma                90.00
_cell_volume                     2028.3(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    3801
_cell_measurement_theta_min      2.25
_cell_measurement_theta_max      27.90

_exptl_crystal_description       rod
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.060
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1192
_exptl_absorpt_coefficient_mu    3.152
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.677
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      173(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            19648
_diffrn_reflns_av_R_equivalents  0.0557
_diffrn_reflns_av_sigmaI/netI    0.0510
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.94
_diffrn_reflns_theta_max         28.32
_reflns_number_total             4798
_reflns_number_gt                3540
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker XSCANS'
_computing_cell_refinement       'Bruker XSCANS'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_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+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         4798
_refine_ls_number_parameters     269
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0671
_refine_ls_R_factor_gt           0.0423
_refine_ls_wR_factor_ref         0.1290
_refine_ls_wR_factor_gt          0.1091
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_restrained_S_all      1.037
_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
C1S C 0.4272(6) 0.3995(4) 0.1210(5) 0.0401(13) Uani 1 1 d . . .
H1A H 0.3542 0.3610 0.0941 0.060 Uiso 1 1 calc R . .
H1B H 0.4457 0.4428 0.0732 0.060 Uiso 1 1 calc R . .
H1C H 0.3897 0.4240 0.1810 0.060 Uiso 1 1 calc R . .
O1S O 0.5600(5) 0.3572(3) 0.1424(3) 0.0361(9) Uani 1 1 d . . .
H1S H 0.580(7) 0.336(4) 0.097(5) 0.043 Uiso 1 1 d . . .
N11 N 0.6152(5) 0.2582(3) 0.3069(3) 0.0265(9) Uani 1 1 d . . .
H11 H 0.606(6) 0.290(4) 0.264(4) 0.032 Uiso 1 1 d . . .
C12 C 0.5654(5) 0.2634(3) 0.4003(3) 0.0270(10) Uani 1 1 d . . .
N13 N 0.6104(5) 0.2022(3) 0.4558(3) 0.0284(9) Uani 1 1 d . . .
C14 C 0.6976(5) 0.1551(3) 0.3965(4) 0.0268(10) Uani 1 1 d . . .
C15 C 0.7743(6) 0.0825(3) 0.4166(4) 0.0306(11) Uani 1 1 d . . .
H15 H 0.7729 0.0581 0.4796 0.037 Uiso 1 1 calc R . .
C16 C 0.8519(6) 0.0475(3) 0.3417(4) 0.0344(12) Uani 1 1 d . . .
H16 H 0.9048 -0.0018 0.3535 0.041 Uiso 1 1 calc R . .
C17 C 0.8546(6) 0.0831(3) 0.2484(4) 0.0365(12) Uani 1 1 d . . .
H17 H 0.9101 0.0576 0.1987 0.044 Uiso 1 1 calc R . .
C18 C 0.7788(6) 0.1540(3) 0.2274(4) 0.0336(11) Uani 1 1 d . . .
H18 H 0.7802 0.1780 0.1642 0.040 Uiso 1 1 calc R . .
C19 C 0.7004(5) 0.1889(3) 0.3024(4) 0.0267(10) Uani 1 1 d . . .
N21 N 0.2938(5) 0.4604(3) 0.4916(3) 0.0347(10) Uani 1 1 d . . .
C22 C 0.3004(7) 0.3901(4) 0.5402(4) 0.0385(13) Uani 1 1 d . . .
H22 H 0.2403 0.3841 0.5958 0.046 Uiso 1 1 calc R . .
C23 C 0.3898(6) 0.3248(3) 0.5149(4) 0.0344(12) Uani 1 1 d . . .
H23 H 0.3939 0.2766 0.5538 0.041 Uiso 1 1 calc R . .
C24 C 0.4727(5) 0.3316(3) 0.4316(4) 0.0265(10) Uani 1 1 d . . .
C25 C 0.4671(6) 0.4047(3) 0.3801(4) 0.0322(11) Uani 1 1 d . . .
H25 H 0.5244 0.4123 0.3235 0.039 Uiso 1 1 calc R . .
C26 C 0.3764(6) 0.4664(4) 0.4131(4) 0.0351(12) Uani 1 1 d . . .
H26 H 0.3729 0.5162 0.3772 0.042 Uiso 1 1 calc R . .
C31 C -0.0106(5) 0.6958(3) 0.5899(4) 0.0287(11) Uani 1 1 d . . .
I31 I 0.11791(4) 0.59406(2) 0.55373(3) 0.03129(13) Uani 1 1 d . . .
C32 C -0.0210(6) 0.7621(3) 0.5291(4) 0.0323(11) Uani 1 1 d . . .
F32 F 0.0511(4) 0.7633(2) 0.4445(2) 0.0448(8) Uani 1 1 d . . .
C33 C -0.1036(6) 0.8299(3) 0.5530(4) 0.0303(11) Uani 1 1 d . . .
F33 F -0.1061(4) 0.8941(2) 0.4907(3) 0.0430(8) Uani 1 1 d . . .
C34 C -0.1810(6) 0.8332(3) 0.6371(4) 0.0307(11) Uani 1 1 d . . .
I34 I -0.29722(5) 0.93785(3) 0.67294(3) 0.04743(15) Uani 1 1 d . . .
C35 C -0.1714(6) 0.7667(4) 0.6982(4) 0.0370(12) Uani 1 1 d . . .
F35 F -0.2459(4) 0.7657(2) 0.7822(3) 0.0529(9) Uani 1 1 d . . .
C36 C -0.0884(6) 0.6994(3) 0.6758(4) 0.0343(12) Uani 1 1 d . . .
F36 F -0.0842(4) 0.6361(2) 0.7382(3) 0.0500(9) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1S O1S 1.415(7) . ?
C1S H1A 0.9800 . ?
C1S H1B 0.9800 . ?
C1S H1C 0.9800 . ?
O1S H1S 0.73(7) . ?
N11 C12 1.367(6) . ?
N11 C19 1.372(6) . ?
N11 H11 0.79(6) . ?
C12 N13 1.314(6) . ?
C12 C24 1.464(7) . ?
N13 C14 1.379(6) . ?
C14 C15 1.399(7) . ?
C14 C19 1.402(7) . ?
C15 C16 1.379(7) . ?
C15 H15 0.9500 . ?
C16 C17 1.405(8) . ?
C16 H16 0.9500 . ?
C17 C18 1.374(8) . ?
C17 H17 0.9500 . ?
C18 C19 1.383(7) . ?
C18 H18 0.9500 . ?
N21 C26 1.326(7) . ?
N21 C22 1.327(7) . ?
C22 C23 1.386(8) . ?
C22 H22 0.9500 . ?
C23 C24 1.383(7) . ?
C23 H23 0.9500 . ?
C24 C25 1.386(7) . ?
C25 C26 1.381(8) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?
C31 C32 1.366(7) . ?
C31 C36 1.385(7) . ?
C31 I31 2.094(5) . ?
C32 F32 1.341(6) . ?
C32 C33 1.379(7) . ?
C33 F33 1.350(6) . ?
C33 C34 1.361(7) . ?
C34 C35 1.372(8) . ?
C34 I34 2.071(5) . ?
C35 F35 1.345(6) . ?
C35 C36 1.370(8) . ?
C36 F36 1.340(6) . ?

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
O1S C1S H1A 109.5 . . ?
O1S C1S H1B 109.5 . . ?
H1A C1S H1B 109.5 . . ?
O1S C1S H1C 109.5 . . ?
H1A C1S H1C 109.5 . . ?
H1B C1S H1C 109.5 . . ?
C1S O1S H1S 106(5) . . ?
C12 N11 C19 106.8(4) . . ?
C12 N11 H11 128(4) . . ?
C19 N11 H11 125(4) . . ?
N13 C12 N11 112.9(4) . . ?
N13 C12 C24 125.6(4) . . ?
N11 C12 C24 121.5(4) . . ?
C12 N13 C14 104.9(4) . . ?
N13 C14 C15 130.1(5) . . ?
N13 C14 C19 110.0(4) . . ?
C15 C14 C19 119.8(5) . . ?
C16 C15 C14 117.6(5) . . ?
C16 C15 H15 121.2 . . ?
C14 C15 H15 121.2 . . ?
C15 C16 C17 121.6(5) . . ?
C15 C16 H16 119.2 . . ?
C17 C16 H16 119.2 . . ?
C18 C17 C16 121.4(5) . . ?
C18 C17 H17 119.3 . . ?
C16 C17 H17 119.3 . . ?
C17 C18 C19 117.0(5) . . ?
C17 C18 H18 121.5 . . ?
C19 C18 H18 121.5 . . ?
N11 C19 C18 132.2(5) . . ?
N11 C19 C14 105.3(4) . . ?
C18 C19 C14 122.6(5) . . ?
C26 N21 C22 116.7(5) . . ?
N21 C22 C23 124.0(5) . . ?
N21 C22 H22 118.0 . . ?
C23 C22 H22 118.0 . . ?
C24 C23 C22 118.4(5) . . ?
C24 C23 H23 120.8 . . ?
C22 C23 H23 120.8 . . ?
C23 C24 C25 118.2(5) . . ?
C23 C24 C12 120.3(5) . . ?
C25 C24 C12 121.5(5) . . ?
C26 C25 C24 118.5(5) . . ?
C26 C25 H25 120.8 . . ?
C24 C25 H25 120.8 . . ?
N21 C26 C25 124.2(5) . . ?
N21 C26 H26 117.9 . . ?
C25 C26 H26 117.9 . . ?
C32 C31 C36 117.0(5) . . ?
C32 C31 I31 121.1(4) . . ?
C36 C31 I31 122.0(4) . . ?
F32 C32 C31 120.5(5) . . ?
F32 C32 C33 118.0(5) . . ?
C31 C32 C33 121.4(5) . . ?
F33 C33 C34 120.1(5) . . ?
F33 C33 C32 118.3(5) . . ?
C34 C33 C32 121.6(5) . . ?
C33 C34 C35 117.2(5) . . ?
C33 C34 I34 120.4(4) . . ?
C35 C34 I34 122.3(4) . . ?
F35 C35 C36 118.0(5) . . ?
F35 C35 C34 120.3(5) . . ?
C36 C35 C34 121.8(5) . . ?
F36 C36 C35 118.9(5) . . ?
F36 C36 C31 120.0(5) . . ?
C35 C36 C31 121.0(5) . . ?

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
C19 N11 C12 N13 -0.8(6) . . . . ?
C19 N11 C12 C24 178.8(4) . . . . ?
N11 C12 N13 C14 1.5(5) . . . . ?
C24 C12 N13 C14 -178.1(5) . . . . ?
C12 N13 C14 C15 -179.9(5) . . . . ?
C12 N13 C14 C19 -1.5(5) . . . . ?
N13 C14 C15 C16 179.0(5) . . . . ?
C19 C14 C15 C16 0.8(7) . . . . ?
C14 C15 C16 C17 0.0(8) . . . . ?
C15 C16 C17 C18 -0.6(8) . . . . ?
C16 C17 C18 C19 0.3(8) . . . . ?
C12 N11 C19 C18 -179.4(5) . . . . ?
C12 N11 C19 C14 -0.2(5) . . . . ?
C17 C18 C19 N11 179.6(5) . . . . ?
C17 C18 C19 C14 0.5(8) . . . . ?
N13 C14 C19 N11 1.1(5) . . . . ?
C15 C14 C19 N11 179.6(4) . . . . ?
N13 C14 C19 C18 -179.6(5) . . . . ?
C15 C14 C19 C18 -1.1(8) . . . . ?
C26 N21 C22 C23 1.5(9) . . . . ?
N21 C22 C23 C24 -2.9(9) . . . . ?
C22 C23 C24 C25 2.8(8) . . . . ?
C22 C23 C24 C12 -178.2(5) . . . . ?
N13 C12 C24 C23 -19.1(8) . . . . ?
N11 C12 C24 C23 161.4(5) . . . . ?
N13 C12 C24 C25 159.9(5) . . . . ?
N11 C12 C24 C25 -19.6(7) . . . . ?
C23 C24 C25 C26 -1.6(8) . . . . ?
C12 C24 C25 C26 179.4(5) . . . . ?
C22 N21 C26 C25 -0.2(8) . . . . ?
C24 C25 C26 N21 0.3(8) . . . . ?
C36 C31 C32 F32 -179.9(5) . . . . ?
I31 C31 C32 F32 0.1(7) . . . . ?
C36 C31 C32 C33 0.9(8) . . . . ?
I31 C31 C32 C33 -179.0(4) . . . . ?
F32 C32 C33 F33 -0.8(7) . . . . ?
C31 C32 C33 F33 178.4(5) . . . . ?
F32 C32 C33 C34 179.4(5) . . . . ?
C31 C32 C33 C34 -1.5(8) . . . . ?
F33 C33 C34 C35 -178.7(5) . . . . ?
C32 C33 C34 C35 1.1(8) . . . . ?
F33 C33 C34 I34 -2.2(7) . . . . ?
C32 C33 C34 I34 177.6(4) . . . . ?
C33 C34 C35 F35 -179.6(5) . . . . ?
I34 C34 C35 F35 4.0(8) . . . . ?
C33 C34 C35 C36 -0.4(8) . . . . ?
I34 C34 C35 C36 -176.8(4) . . . . ?
F35 C35 C36 F36 -0.4(8) . . . . ?
C34 C35 C36 F36 -179.6(5) . . . . ?
F35 C35 C36 C31 179.1(5) . . . . ?
C34 C35 C36 C31 -0.1(9) . . . . ?
C32 C31 C36 F36 179.3(5) . . . . ?
I31 C31 C36 F36 -0.8(7) . . . . ?
C32 C31 C36 C35 -0.1(8) . . . . ?
I31 C31 C36 C35 179.8(4) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N11 H11 O1S 0.79(6) 2.03(6) 2.810(6) 170(6) .
O1S H1S N13 0.73(7) 2.06(7) 2.778(6) 167(7) 4_565

_diffrn_measured_fraction_theta_max 0.950
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.869
_refine_diff_density_min         -1.183
_refine_diff_density_rms         0.191

#END

data_A5
_database_code_depnum_ccdc_archive 'CCDC 694675'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
[(5-OMe-3-pyridyl)(3-pyridyl)ethyne]4, [1,4-I2-F4-benzene]4
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         
;
(C13 H10 N2 O)4 (C6 F4 I2)3
;
_chemical_formula_sum            'C70 H40 F12 I6 N8 O4'
_chemical_formula_weight         2046.50

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

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

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

_cell_length_a                   7.6881(4)
_cell_length_b                   14.8996(8)
_cell_length_c                   15.3296(8)
_cell_angle_alpha                72.1600(10)
_cell_angle_beta                 88.3640(10)
_cell_angle_gamma                88.5080(10)
_cell_volume                     1670.61(15)
_cell_formula_units_Z            1
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    8531
_cell_measurement_theta_min      2.30
_cell_measurement_theta_max      30.00

_exptl_crystal_description       plate
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.02
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.034
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             974
_exptl_absorpt_coefficient_mu    2.880
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.495
_exptl_absorpt_correction_T_max  1.000
_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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            19870
_diffrn_reflns_av_R_equivalents  0.0272
_diffrn_reflns_av_sigmaI/netI    0.0402
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.65
_diffrn_reflns_theta_max         30.03
_reflns_number_total             9596
_reflns_number_gt                8511
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker XSCANS'
_computing_cell_refinement       'Bruker XSCANS'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_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)+(0.0400P)²+0.7000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         9596
_refine_ls_number_parameters     453
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0373
_refine_ls_R_factor_gt           0.0315
_refine_ls_wR_factor_ref         0.0763
_refine_ls_wR_factor_gt          0.0733
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_restrained_S_all      1.006
_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 0.52207(2) 0.703825(12) 0.729767(11) 0.01567(5) Uani 1 1 d . . .
I2 I 0.81198(2) 0.509974(12) 0.385667(11) 0.01602(5) Uani 1 1 d . . .
I3 I 0.87092(2) 0.225879(13) 0.501047(13) 0.02351(5) Uani 1 1 d . . .
N11 N 0.4506(3) 0.78019(17) 0.87137(16) 0.0185(5) Uani 1 1 d . . .
C12 C 0.3558(4) 0.8585(2) 0.86509(19) 0.0192(5) Uani 1 1 d . . .
H12 H 0.3020 0.8905 0.8087 0.023 Uiso 1 1 calc R . .
C13 C 0.3333(3) 0.89468(19) 0.93883(18) 0.0174(5) Uani 1 1 d . . .
C14 C 0.4084(3) 0.84654(19) 1.02258(19) 0.0174(5) Uani 1 1 d . . .
H14 H 0.3953 0.8695 1.0738 0.021 Uiso 1 1 calc R . .
C15 C 0.5026(4) 0.76436(19) 1.02889(19) 0.0180(5) Uani 1 1 d . . .
C16 C 0.5238(4) 0.7348(2) 0.95080(19) 0.0188(5) Uani 1 1 d . . .
H16 H 0.5933 0.6801 0.9547 0.023 Uiso 1 1 calc R . .
C17 C 0.2345(4) 0.9803(2) 0.92628(19) 0.0193(5) Uani 1 1 d . . .
C18 C 0.5573(4) 0.7347(2) 1.18734(19) 0.0214(6) Uani 1 1 d . . .
H18A H 0.6224 0.6905 1.2369 0.032 Uiso 1 1 calc R . .
H18B H 0.4336 0.7336 1.2048 0.032 Uiso 1 1 calc R . .
H18C H 0.6011 0.7986 1.1763 0.032 Uiso 1 1 calc R . .
N21 N -0.0381(3) 1.28377(17) 0.91280(17) 0.0212(5) Uani 1 1 d . . .
C22 C 0.0365(4) 1.1979(2) 0.93933(19) 0.0197(5) Uani 1 1 d . . .
H22 H 0.0735 1.1734 1.0009 0.024 Uiso 1 1 calc R . .
C23 C 0.0630(3) 1.14218(19) 0.88092(19) 0.0181(5) Uani 1 1 d . . .
C24 C 0.0085(4) 1.1786(2) 0.79094(19) 0.0203(5) Uani 1 1 d . . .
H24 H 0.0231 1.1427 0.7495 0.024 Uiso 1 1 calc R . .
C25 C -0.0670(4) 1.2672(2) 0.7627(2) 0.0224(6) Uani 1 1 d . . .
H25 H -0.1045 1.2938 0.7015 0.027 Uiso 1 1 calc R . .
O25 O 0.5789(3) 0.70781(15) 1.10525(14) 0.0226(4) Uani 1 1 d . . .
C26 C -0.0871(4) 1.3170(2) 0.8255(2) 0.0227(6) Uani 1 1 d . . .
H26 H -0.1386 1.3783 0.8053 0.027 Uiso 1 1 calc R . .
C27 C 0.1532(4) 1.0530(2) 0.91026(19) 0.0196(5) Uani 1 1 d . . .
N31 N 0.8942(3) 0.44780(17) 0.23574(16) 0.0189(5) Uani 1 1 d . . .
C32 C 0.9700(4) 0.3647(2) 0.24220(19) 0.0185(5) Uani 1 1 d . . .
H32 H 1.0282 0.3323 0.2971 0.022 Uiso 1 1 calc R . .
C33 C 0.9680(3) 0.32314(19) 0.17258(19) 0.0174(5) Uani 1 1 d . . .
C34 C 0.8862(3) 0.37133(19) 0.09038(19) 0.0174(5) Uani 1 1 d . . .
H34 H 0.8852 0.3458 0.0407 0.021 Uiso 1 1 calc R . .
C35 C 0.8065(3) 0.45781(19) 0.08422(19) 0.0170(5) Uani 1 1 d . . .
O35 O 0.7193(3) 0.51269(14) 0.01109(13) 0.0217(4) Uani 1 1 d . . .
C36 C 0.8128(4) 0.49363(19) 0.15840(19) 0.0177(5) Uani 1 1 d . . .
H36 H 0.7573 0.5526 0.1537 0.021 Uiso 1 1 calc R . .
C37 C 1.0503(4) 0.2326(2) 0.18709(19) 0.0189(5) Uani 1 1 d . . .
C38 C 0.7157(4) 0.4814(2) -0.06841(19) 0.0215(6) Uani 1 1 d . . .
H38A H 0.6512 0.5277 -0.1168 0.032 Uiso 1 1 calc R . .
H38B H 0.6584 0.4204 -0.0527 0.032 Uiso 1 1 calc R . .
H38C H 0.8350 0.4748 -0.0901 0.032 Uiso 1 1 calc R . .
N41 N 1.3659(3) -0.06122(18) 0.20448(18) 0.0240(5) Uani 1 1 d . . .
C42 C 1.2613(4) 0.0150(2) 0.1811(2) 0.0206(5) Uani 1 1 d . . .
H42 H 1.2049 0.0306 0.1239 0.025 Uiso 1 1 calc R . .
C43 C 1.2309(3) 0.07303(19) 0.23705(19) 0.0178(5) Uani 1 1 d . . .
C44 C 1.3121(4) 0.0490(2) 0.32129(19) 0.0199(5) Uani 1 1 d . . .
H44 H 1.2941 0.0864 0.3612 0.024 Uiso 1 1 calc R . .
C45 C 1.4197(4) -0.0303(2) 0.3459(2) 0.0224(6) Uani 1 1 d . . .
H45 H 1.4761 -0.0488 0.4032 0.027 Uiso 1 1 calc R . .
C46 C 1.4432(4) -0.0820(2) 0.2854(2) 0.0248(6) Uani 1 1 d . . .
H46 H 1.5190 -0.1357 0.3023 0.030 Uiso 1 1 calc R . .
C47 C 1.1261(4) 0.1579(2) 0.20735(19) 0.0190(5) Uani 1 1 d . . .
C51 C 0.6054(3) 0.64490(19) 0.62781(18) 0.0162(5) Uani 1 1 d . . .
C52 C 0.6304(3) 0.54864(19) 0.64501(17) 0.0157(5) Uani 1 1 d . . .
F52 F 0.5975(2) 0.48946(12) 0.72976(11) 0.0210(3) Uani 1 1 d . . .
C53 C 0.6857(3) 0.51037(19) 0.57746(19) 0.0167(5) Uani 1 1 d . . .
F53 F 0.7026(2) 0.41557(11) 0.59899(11) 0.0221(3) Uani 1 1 d . . .
C54 C 0.7228(3) 0.56636(19) 0.48911(18) 0.0165(5) Uani 1 1 d . . .
C55 C 0.6971(3) 0.66240(19) 0.47163(18) 0.0168(5) Uani 1 1 d . . .
F55 F 0.7303(2) 0.72169(12) 0.38647(11) 0.0231(4) Uani 1 1 d . . .
C56 C 0.6413(3) 0.70061(19) 0.53883(18) 0.0166(5) Uani 1 1 d . . .
F56 F 0.6242(2) 0.79543(12) 0.51686(11) 0.0230(3) Uani 1 1 d . . .
C61 C 0.9479(4) 0.0913(2) 0.50040(19) 0.0194(5) Uani 1 1 d . . .
C62 C 1.0662(4) 0.0376(2) 0.56324(19) 0.0207(5) Uani 1 1 d . . .
F62 F 1.1328(2) 0.07112(13) 0.62654(12) 0.0274(4) Uani 1 1 d . . .
C66 C 0.8826(4) 0.0519(2) 0.43781(19) 0.0210(5) Uani 1 1 d . . .
F66 F 0.7682(2) 0.10026(13) 0.37568(12) 0.0291(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 C51 2.092(3) . ?
I2 C54 2.101(3) . ?
I3 C61 2.079(3) . ?
N11 C16 1.331(4) . ?
N11 C12 1.339(4) . ?
C12 C13 1.398(4) . ?
C12 H12 0.9500 . ?
C13 C14 1.397(4) . ?
C13 C17 1.432(4) . ?
C14 C15 1.385(4) . ?
C14 H14 0.9500 . ?
C15 O25 1.354(3) . ?
C15 C16 1.401(4) . ?
C16 H16 0.9500 . ?
C17 C27 1.198(4) . ?
C18 O25 1.438(3) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
N21 C22 1.337(4) . ?
N21 C26 1.339(4) . ?
C22 C23 1.403(4) . ?
C22 H22 0.9500 . ?
C23 C24 1.391(4) . ?
C23 C27 1.432(4) . ?
C24 C25 1.376(4) . ?
C24 H24 0.9500 . ?
C25 C26 1.387(4) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?
N31 C32 1.331(4) . ?
N31 C36 1.337(4) . ?
C32 C33 1.389(4) . ?
C32 H32 0.9500 . ?
C33 C34 1.402(4) . ?
C33 C37 1.432(4) . ?
C34 C35 1.390(4) . ?
C34 H34 0.9500 . ?
C35 O35 1.352(3) . ?
C35 C36 1.399(4) . ?
O35 C38 1.433(3) . ?
C36 H36 0.9500 . ?
C37 C47 1.199(4) . ?
C38 H38A 0.9800 . ?
C38 H38B 0.9800 . ?
C38 H38C 0.9800 . ?
N41 C42 1.335(4) . ?
N41 C46 1.336(4) . ?
C42 C43 1.404(4) . ?
C42 H42 0.9500 . ?
C43 C44 1.392(4) . ?
C43 C47 1.439(4) . ?
C44 C45 1.385(4) . ?
C44 H44 0.9500 . ?
C45 C46 1.382(4) . ?
C45 H45 0.9500 . ?
C46 H46 0.9500 . ?
C51 C52 1.386(4) . ?
C51 C56 1.386(4) . ?
C52 F52 1.349(3) . ?
C52 C53 1.379(4) . ?
C53 F53 1.352(3) . ?
C53 C54 1.382(4) . ?
C54 C55 1.383(4) . ?
C55 F55 1.355(3) . ?
C55 C56 1.375(4) . ?
C56 F56 1.352(3) . ?
C61 C66 1.380(4) . ?
C61 C62 1.391(4) . ?
C62 F62 1.338(3) . ?
C62 C66 1.386(4) 2_756 ?
C66 F66 1.339(3) . ?
C66 C62 1.386(4) 2_756 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C16 N11 C12 118.8(2) . . ?
N11 C12 C13 122.1(3) . . ?
N11 C12 H12 118.9 . . ?
C13 C12 H12 118.9 . . ?
C14 C13 C12 119.2(2) . . ?
C14 C13 C17 121.8(2) . . ?
C12 C13 C17 119.0(2) . . ?
C15 C14 C13 118.2(3) . . ?
C15 C14 H14 120.9 . . ?
C13 C14 H14 120.9 . . ?
O25 C15 C14 125.8(2) . . ?
O25 C15 C16 115.2(2) . . ?
C14 C15 C16 119.0(3) . . ?
N11 C16 C15 122.7(3) . . ?
N11 C16 H16 118.7 . . ?
C15 C16 H16 118.7 . . ?
C27 C17 C13 176.1(3) . . ?
O25 C18 H18A 109.5 . . ?
O25 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
O25 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C22 N21 C26 117.1(3) . . ?
N21 C22 C23 123.3(3) . . ?
N21 C22 H22 118.3 . . ?
C23 C22 H22 118.3 . . ?
C24 C23 C22 118.0(3) . . ?
C24 C23 C27 120.3(3) . . ?
C22 C23 C27 121.6(2) . . ?
C25 C24 C23 119.2(3) . . ?
C25 C24 H24 120.4 . . ?
C23 C24 H24 120.4 . . ?
C24 C25 C26 118.6(3) . . ?
C24 C25 H25 120.7 . . ?
C26 C25 H25 120.7 . . ?
C15 O25 C18 116.9(2) . . ?
N21 C26 C25 123.9(3) . . ?
N21 C26 H26 118.1 . . ?
C25 C26 H26 118.1 . . ?
C17 C27 C23 173.7(3) . . ?
C32 N31 C36 118.4(2) . . ?
N31 C32 C33 123.2(3) . . ?
N31 C32 H32 118.4 . . ?
C33 C32 H32 118.4 . . ?
C32 C33 C34 119.0(3) . . ?
C32 C33 C37 118.8(3) . . ?
C34 C33 C37 122.2(3) . . ?
C35 C34 C33 117.6(3) . . ?
C35 C34 H34 121.2 . . ?
C33 C34 H34 121.2 . . ?
O35 C35 C34 125.4(2) . . ?
O35 C35 C36 115.1(2) . . ?
C34 C35 C36 119.5(2) . . ?
C35 O35 C38 117.4(2) . . ?
N31 C36 C35 122.3(2) . . ?
N31 C36 H36 118.8 . . ?
C35 C36 H36 118.8 . . ?
C47 C37 C33 173.2(3) . . ?
O35 C38 H38A 109.5 . . ?
O35 C38 H38B 109.5 . . ?
H38A C38 H38B 109.5 . . ?
O35 C38 H38C 109.5 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 109.5 . . ?
C42 N41 C46 117.4(3) . . ?
N41 C42 C43 123.1(3) . . ?
N41 C42 H42 118.4 . . ?
C43 C42 H42 118.4 . . ?
C44 C43 C42 118.2(3) . . ?
C44 C43 C47 120.0(3) . . ?
C42 C43 C47 121.7(3) . . ?
C45 C44 C43 118.8(3) . . ?
C45 C44 H44 120.6 . . ?
C43 C44 H44 120.6 . . ?
C46 C45 C44 118.6(3) . . ?
C46 C45 H45 120.7 . . ?
C44 C45 H45 120.7 . . ?
N41 C46 C45 124.0(3) . . ?
N41 C46 H46 118.0 . . ?
C45 C46 H46 118.0 . . ?
C37 C47 C43 173.4(3) . . ?
C52 C51 C56 116.0(2) . . ?
C52 C51 I1 122.40(19) . . ?
C56 C51 I1 121.6(2) . . ?
F52 C52 C53 118.2(2) . . ?
F52 C52 C51 119.7(2) . . ?
C53 C52 C51 122.0(2) . . ?
F53 C53 C52 118.6(2) . . ?
F53 C53 C54 119.8(2) . . ?
C52 C53 C54 121.7(2) . . ?
C53 C54 C55 116.4(2) . . ?
C53 C54 I2 122.4(2) . . ?
C55 C54 I2 121.2(2) . . ?
F55 C55 C56 118.3(2) . . ?
F55 C55 C54 119.7(2) . . ?
C56 C55 C54 122.0(2) . . ?
F56 C56 C55 118.4(2) . . ?
F56 C56 C51 119.7(2) . . ?
C55 C56 C51 121.9(3) . . ?
C66 C61 C62 117.7(3) . . ?
C66 C61 I3 121.0(2) . . ?
C62 C61 I3 121.2(2) . . ?
F62 C62 C66 118.4(3) . 2_756 ?
F62 C62 C61 120.7(3) . . ?
C66 C62 C61 120.9(3) 2_756 . ?
F66 C66 C61 120.4(3) . . ?
F66 C66 C62 118.2(3) . 2_756 ?
C61 C66 C62 121.4(3) . 2_756 ?

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 0.9(4) . . . . ?
N11 C12 C13 C14 -1.6(4) . . . . ?
N11 C12 C13 C17 178.1(3) . . . . ?
C12 C13 C14 C15 0.0(4) . . . . ?
C17 C13 C14 C15 -179.8(3) . . . . ?
C13 C14 C15 O25 -177.8(3) . . . . ?
C13 C14 C15 C16 2.2(4) . . . . ?
C12 N11 C16 C15 1.5(4) . . . . ?
O25 C15 C16 N11 177.0(2) . . . . ?
C14 C15 C16 N11 -3.1(4) . . . . ?
C26 N21 C22 C23 -0.7(4) . . . . ?
N21 C22 C23 C24 0.0(4) . . . . ?
N21 C22 C23 C27 176.0(3) . . . . ?
C22 C23 C24 C25 0.7(4) . . . . ?
C27 C23 C24 C25 -175.5(3) . . . . ?
C23 C24 C25 C26 -0.5(4) . . . . ?
C14 C15 O25 C18 1.2(4) . . . . ?
C16 C15 O25 C18 -178.8(2) . . . . ?
C22 N21 C26 C25 1.0(4) . . . . ?
C24 C25 C26 N21 -0.4(5) . . . . ?
C36 N31 C32 C33 -0.3(4) . . . . ?
N31 C32 C33 C34 1.6(4) . . . . ?
N31 C32 C33 C37 -178.7(3) . . . . ?
C32 C33 C34 C35 -1.8(4) . . . . ?
C37 C33 C34 C35 178.5(3) . . . . ?
C33 C34 C35 O35 -178.7(2) . . . . ?
C33 C34 C35 C36 0.9(4) . . . . ?
C34 C35 O35 C38 -3.2(4) . . . . ?
C36 C35 O35 C38 177.2(2) . . . . ?
C32 N31 C36 C35 -0.7(4) . . . . ?
O35 C35 C36 N31 -180.0(2) . . . . ?
C34 C35 C36 N31 0.4(4) . . . . ?
C46 N41 C42 C43 0.3(4) . . . . ?
N41 C42 C43 C44 -0.8(4) . . . . ?
N41 C42 C43 C47 176.0(3) . . . . ?
C42 C43 C44 C45 0.4(4) . . . . ?
C47 C43 C44 C45 -176.6(3) . . . . ?
C43 C44 C45 C46 0.6(4) . . . . ?
C42 N41 C46 C45 0.8(4) . . . . ?
C44 C45 C46 N41 -1.2(5) . . . . ?
C56 C51 C52 F52 -179.7(2) . . . . ?
I1 C51 C52 F52 1.2(3) . . . . ?
C56 C51 C52 C53 -0.7(4) . . . . ?
I1 C51 C52 C53 -179.9(2) . . . . ?
F52 C52 C53 F53 0.7(4) . . . . ?
C51 C52 C53 F53 -178.3(2) . . . . ?
F52 C52 C53 C54 -179.6(2) . . . . ?
C51 C52 C53 C54 1.4(4) . . . . ?
F53 C53 C54 C55 178.0(2) . . . . ?
C52 C53 C54 C55 -1.7(4) . . . . ?
F53 C53 C54 I2 -1.6(4) . . . . ?
C52 C53 C54 I2 178.8(2) . . . . ?
C53 C54 C55 F55 -179.8(2) . . . . ?
I2 C54 C55 F55 -0.3(3) . . . . ?
C53 C54 C55 C56 1.4(4) . . . . ?
I2 C54 C55 C56 -179.0(2) . . . . ?
F55 C55 C56 F56 -0.7(4) . . . . ?
C54 C55 C56 F56 178.0(2) . . . . ?
F55 C55 C56 C51 -179.6(2) . . . . ?
C54 C55 C56 C51 -0.9(4) . . . . ?
C52 C51 C56 F56 -178.4(2) . . . . ?
I1 C51 C56 F56 0.7(4) . . . . ?
C52 C51 C56 C55 0.5(4) . . . . ?
I1 C51 C56 C55 179.6(2) . . . . ?
C66 C61 C62 F62 -179.1(2) . . . . ?
I3 C61 C62 F62 0.5(4) . . . . ?
C66 C61 C62 C66 0.5(5) . . . 2_756 ?
I3 C61 C62 C66 -179.8(2) . . . 2_756 ?
C62 C61 C66 F66 180.0(2) . . . . ?
I3 C61 C66 F66 0.3(4) . . . . ?
C62 C61 C66 C62 -0.5(5) . . . 2_756 ?
I3 C61 C66 C62 179.8(2) . . . 2_756 ?

_diffrn_measured_fraction_theta_max 0.983
_diffrn_reflns_theta_full        30.03
_diffrn_measured_fraction_theta_full 0.983
_refine_diff_density_max         1.588
_refine_diff_density_min         -0.696
_refine_diff_density_rms         0.144

#END

data_A6
_database_code_depnum_ccdc_archive 'CCDC 694676'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
(5-methoxy-3,3'-bipyridyl)2, (1,4-diiodotetrafluorobenzene)3
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         
;
(C11 H10 N2 O)2 (C6 F4 I2)3
;
_chemical_formula_sum            'C40 H20 F12 I6 N4 O2'
_chemical_formula_weight         1578.00

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                   7.2012(7)
_cell_length_b                   17.6878(15)
_cell_length_c                   17.7138(16)
_cell_angle_alpha                89.927(4)
_cell_angle_beta                 82.869(7)
_cell_angle_gamma                88.275(6)
_cell_volume                     2237.8(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    2864
_cell_measurement_theta_min      2.30
_cell_measurement_theta_max      26.65

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.342
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1460
_exptl_absorpt_coefficient_mu    4.255
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.513
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      173(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            27838
_diffrn_reflns_av_R_equivalents  0.1017
_diffrn_reflns_av_sigmaI/netI    0.1405
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         1.63
_diffrn_reflns_theta_max         27.86
_reflns_number_total             10109
_reflns_number_gt                5894
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker XSCANS'
_computing_cell_refinement       'Bruker XSCANS'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_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)+(0.1000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         10109
_refine_ls_number_parameters     579
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1346
_refine_ls_R_factor_gt           0.0650
_refine_ls_wR_factor_ref         0.1989
_refine_ls_wR_factor_gt          0.1588
_refine_ls_goodness_of_fit_ref   1.008
_refine_ls_restrained_S_all      1.008
_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 0.5175(15) 0.5049(5) 0.3092(6) 0.031(2) Uani 1 1 d . . .
C12 C 0.4959(18) 0.4546(6) 0.2548(7) 0.030(3) Uani 1 1 d . . .
H12 H 0.5163 0.4708 0.2033 0.036 Uiso 1 1 calc R . .
C13 C 0.4463(15) 0.3814(6) 0.2686(6) 0.021(2) Uani 1 1 d . . .
C14 C 0.4154(16) 0.3590(6) 0.3447(6) 0.023(2) Uani 1 1 d . . .
H14 H 0.3792 0.3089 0.3576 0.027 Uiso 1 1 calc R . .
C15 C 0.4382(17) 0.4105(6) 0.4007(6) 0.026(3) Uani 1 1 d . . .
O15 O 0.4177(13) 0.3954(5) 0.4764(4) 0.034(2) Uani 1 1 d . . .
C17 C 0.3995(18) 0.3178(7) 0.4994(7) 0.035(3) Uani 1 1 d . . .
H17A H 0.4124 0.3135 0.5537 0.053 Uiso 1 1 calc R . .
H17B H 0.4975 0.2866 0.4699 0.053 Uiso 1 1 calc R . .
H17C H 0.2763 0.3004 0.4904 0.053 Uiso 1 1 calc R . .
C16 C 0.4882(19) 0.4827(7) 0.3804(7) 0.035(3) Uani 1 1 d . . .
H16 H 0.5021 0.5181 0.4194 0.042 Uiso 1 1 calc R . .
N21 N 0.4406(15) 0.2027(5) 0.1560(6) 0.031(2) Uani 1 1 d . . .
C22 C 0.4529(19) 0.2533(6) 0.2111(6) 0.031(3) Uani 1 1 d . . .
H22 H 0.4857 0.2347 0.2582 0.037 Uiso 1 1 calc R . .
C23 C 0.4216(16) 0.3302(7) 0.2050(6) 0.026(3) Uani 1 1 d . . .
C24 C 0.3773(19) 0.3564(7) 0.1362(7) 0.033(3) Uani 1 1 d . . .
H24 H 0.3513 0.4088 0.1297 0.040 Uiso 1 1 calc R . .
C25 C 0.3704(18) 0.3071(7) 0.0766(6) 0.031(3) Uani 1 1 d . . .
H25 H 0.3407 0.3247 0.0287 0.037 Uiso 1 1 calc R . .
C26 C 0.4072(17) 0.2324(7) 0.0883(6) 0.030(3) Uani 1 1 d . . .
H26 H 0.4097 0.1989 0.0463 0.036 Uiso 1 1 calc R . .
N31 N -0.1098(14) 0.3124(6) 0.4974(5) 0.033(2) Uani 1 1 d . . .
C32 C -0.0967(18) 0.2563(6) 0.5481(6) 0.029(3) Uani 1 1 d . . .
H32 H -0.1227 0.2065 0.5332 0.035 Uiso 1 1 calc R . .
C33 C -0.0480(18) 0.2666(7) 0.6201(6) 0.029(3) Uani 1 1 d . . .
C34 C -0.0195(18) 0.3413(6) 0.6442(7) 0.029(3) Uani 1 1 d . . .
H34 H 0.0140 0.3516 0.6933 0.034 Uiso 1 1 calc R . .
C35 C -0.0438(17) 0.3995(6) 0.5913(6) 0.027(3) Uani 1 1 d . . .
O35 O -0.0254(13) 0.4741(4) 0.6063(4) 0.034(2) Uani 1 1 d . . .
C37 C -0.002(2) 0.4956(7) 0.6825(7) 0.038(3) Uani 1 1 d . . .
H37A H 0.0012 0.5508 0.6860 0.056 Uiso 1 1 calc R . .
H37B H 0.1163 0.4733 0.6958 0.056 Uiso 1 1 calc R . .
H37C H -0.1061 0.4772 0.7178 0.056 Uiso 1 1 calc R . .
C36 C -0.0902(19) 0.3815(7) 0.5199(7) 0.036(3) Uani 1 1 d . . .
H36 H -0.1085 0.4216 0.4857 0.043 Uiso 1 1 calc R . .
N41 N -0.0418(16) 0.1507(6) 0.7970(5) 0.035(3) Uani 1 1 d . . .
C42 C -0.0584(18) 0.2077(7) 0.7496(6) 0.032(3) Uani 1 1 d . . .
H42 H -0.0977 0.2555 0.7712 0.039 Uiso 1 1 calc R . .
C43 C -0.0229(17) 0.2031(7) 0.6705(6) 0.028(3) Uani 1 1 d . . .
C44 C 0.0362(19) 0.1322(6) 0.6420(6) 0.032(3) Uani 1 1 d . . .
H44 H 0.0669 0.1256 0.5887 0.038 Uiso 1 1 calc R . .
C45 C 0.0515(18) 0.0711(7) 0.6894(7) 0.033(3) Uani 1 1 d . . .
H45 H 0.0887 0.0224 0.6696 0.039 Uiso 1 1 calc R . .
C46 C 0.0110(18) 0.0832(7) 0.7663(7) 0.032(3) Uani 1 1 d . . .
H46 H 0.0210 0.0414 0.7995 0.039 Uiso 1 1 calc R . .
C51 C 0.5414(16) 0.7763(6) 0.2356(6) 0.024(2) Uani 1 1 d . . .
I51 I 0.54677(11) 0.66107(4) 0.26451(4) 0.0273(2) Uani 1 1 d . . .
C52 C 0.5189(18) 0.8295(7) 0.2907(7) 0.033(3) Uani 1 1 d . . .
F52 F 0.5101(12) 0.8116(4) 0.3638(4) 0.044(2) Uani 1 1 d . . .
C53 C 0.5005(18) 0.9061(7) 0.2729(7) 0.033(3) Uani 1 1 d . . .
F53 F 0.4828(12) 0.9564(4) 0.3288(4) 0.047(2) Uani 1 1 d . . .
C54 C 0.5103(19) 0.9288(7) 0.1988(7) 0.033(3) Uani 1 1 d . . .
I54 I 0.48090(12) 1.04496(4) 0.17439(5) 0.0329(2) Uani 1 1 d . . .
C55 C 0.5320(17) 0.8747(7) 0.1422(6) 0.027(3) Uani 1 1 d . . .
F55 F 0.5446(11) 0.8945(4) 0.0687(4) 0.0381(18) Uani 1 1 d . . .
C56 C 0.5475(17) 0.7999(6) 0.1605(6) 0.024(3) Uani 1 1 d . . .
F56 F 0.5721(11) 0.7479(4) 0.1038(4) 0.0414(19) Uani 1 1 d . . .
C61 C -0.0767(17) 0.2375(6) 0.2245(6) 0.024(3) Uani 1 1 d . . .
I61 I -0.09359(11) 0.26849(4) 0.34047(4) 0.0266(2) Uani 1 1 d . . .
C62 C -0.0861(17) 0.2926(7) 0.1710(7) 0.029(3) Uani 1 1 d . . .
F62 F -0.1008(11) 0.3657(4) 0.1894(4) 0.0428(19) Uani 1 1 d . . .
C63 C -0.0806(18) 0.2724(7) 0.0948(6) 0.032(3) Uani 1 1 d . . .
F63 F -0.0941(13) 0.3271(4) 0.0447(4) 0.051(2) Uani 1 1 d . . .
C64 C -0.0656(17) 0.1974(7) 0.0719(6) 0.028(3) Uani 1 1 d . . .
I64 I -0.06107(12) 0.17252(5) -0.04400(4) 0.0322(2) Uani 1 1 d . . .
C65 C -0.0517(17) 0.1455(6) 0.1248(7) 0.028(3) Uani 1 1 d . . .
F65 F -0.0309(11) 0.0701(4) 0.1067(4) 0.0374(18) Uani 1 1 d . . .
C66 C -0.0599(16) 0.1628(6) 0.2025(6) 0.023(2) Uani 1 1 d . . .
F66 F -0.0479(12) 0.1083(4) 0.2528(4) 0.0405(19) Uani 1 1 d . . .
C71 C 0.1058(18) 0.5369(6) 0.0483(6) 0.025(3) Uani 1 1 d . . .
I71 I 0.26497(12) 0.59534(4) 0.11783(4) 0.0328(2) Uani 1 1 d . . .
F72 F -0.1583(11) 0.5389(5) 0.1418(4) 0.046(2) Uani 1 1 d . . .
C72 C -0.074(2) 0.5205(7) 0.0716(6) 0.033(3) Uani 1 1 d . . .
F76 F 0.3560(11) 0.5329(5) -0.0503(4) 0.0439(19) Uani 1 1 d . . .
C76 C 0.1818(17) 0.5158(6) -0.0233(6) 0.025(3) Uani 1 1 d . . .
C81 C 0.3883(17) 0.0510(6) 0.4626(6) 0.025(3) Uani 1 1 d . . .
I81 I 0.22495(12) 0.12318(5) 0.40515(4) 0.0330(2) Uani 1 1 d . . .
F82 F 0.6302(11) 0.1373(4) 0.4580(5) 0.047(2) Uani 1 1 d . . .
C82 C 0.5635(19) 0.0696(6) 0.4790(6) 0.031(3) Uani 1 1 d . . .
F86 F 0.1595(10) -0.0435(4) 0.4690(5) 0.045(2) Uani 1 1 d . . .
C86 C 0.3268(16) -0.0194(7) 0.4852(7) 0.028(3) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N11 C16 1.314(16) . ?
N11 C12 1.339(14) . ?
C12 C13 1.367(15) . ?
C12 H12 0.9500 . ?
C13 C14 1.399(15) . ?
C13 C23 1.477(14) . ?
C14 C15 1.376(15) . ?
C14 H14 0.9500 . ?
C15 O15 1.358(13) . ?
C15 C16 1.373(17) . ?
O15 C17 1.436(14) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C16 H16 0.9500 . ?
N21 C22 1.338(13) . ?
N21 C26 1.353(15) . ?
C22 C23 1.378(15) . ?
C22 H22 0.9500 . ?
C23 C24 1.376(16) . ?
C24 C25 1.376(15) . ?
C24 H24 0.9500 . ?
C25 C26 1.361(16) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?
N31 C36 1.303(15) . ?
N31 C32 1.347(14) . ?
C32 C33 1.378(15) . ?
C32 H32 0.9500 . ?
C33 C34 1.417(16) . ?
C33 C43 1.456(16) . ?
C34 C35 1.414(15) . ?
C34 H34 0.9500 . ?
C35 O35 1.360(13) . ?
C35 C36 1.386(15) . ?
O35 C37 1.435(13) . ?
C37 H37A 0.9800 . ?
C37 H37B 0.9800 . ?
C37 H37C 0.9800 . ?
C36 H36 0.9500 . ?
N41 C42 1.323(14) . ?
N41 C46 1.337(15) . ?
C42 C43 1.395(15) . ?
C42 H42 0.9500 . ?
C43 C44 1.387(16) . ?
C44 C45 1.378(16) . ?
C44 H44 0.9500 . ?
C45 C46 1.373(16) . ?
C45 H45 0.9500 . ?
C46 H46 0.9500 . ?
C51 C52 1.348(15) . ?
C51 C56 1.389(15) . ?
C51 I51 2.102(11) . ?
C52 F52 1.325(13) . ?
C52 C53 1.398(18) . ?
C53 F53 1.324(12) . ?
C53 C54 1.366(17) . ?
C54 C55 1.378(16) . ?
C54 I54 2.110(12) . ?
C55 F55 1.341(12) . ?
C55 C56 1.366(15) . ?
C56 F56 1.356(11) . ?
C61 C62 1.364(15) . ?
C61 C66 1.375(14) . ?
C61 I61 2.115(10) . ?
C62 F62 1.332(12) . ?
C62 C63 1.392(16) . ?
C63 F63 1.323(13) . ?
C63 C64 1.385(17) . ?
C64 C65 1.321(16) . ?
C64 I64 2.097(11) . ?
C65 F65 1.373(12) . ?
C65 C66 1.403(15) . ?
C66 F66 1.320(12) . ?
C71 C72 1.347(17) . ?
C71 C76 1.367(16) . ?
C71 I71 2.079(11) . ?
F72 C72 1.351(14) . ?
C72 C76 1.395(16) 2_565 ?
F76 C76 1.329(13) . ?
C76 C72 1.395(16) 2_565 ?
C81 C86 1.376(16) . ?
C81 C82 1.380(17) . ?
C81 I81 2.062(11) . ?
F82 C82 1.338(13) . ?
C82 C86 1.377(16) 2_656 ?
F86 C86 1.355(13) . ?
C86 C82 1.377(16) 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
C16 N11 C12 118.0(11) . . ?
N11 C12 C13 124.1(11) . . ?
N11 C12 H12 117.9 . . ?
C13 C12 H12 117.9 . . ?
C12 C13 C14 117.0(10) . . ?
C12 C13 C23 120.5(11) . . ?
C14 C13 C23 122.5(10) . . ?
C15 C14 C13 119.0(10) . . ?
C15 C14 H14 120.5 . . ?
C13 C14 H14 120.5 . . ?
O15 C15 C16 116.0(10) . . ?
O15 C15 C14 124.8(11) . . ?
C16 C15 C14 119.2(10) . . ?
C15 O15 C17 117.8(9) . . ?
O15 C17 H17A 109.5 . . ?
O15 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
O15 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
N11 C16 C15 122.8(10) . . ?
N11 C16 H16 118.6 . . ?
C15 C16 H16 118.6 . . ?
C22 N21 C26 115.3(10) . . ?
N21 C22 C23 125.1(11) . . ?
N21 C22 H22 117.4 . . ?
C23 C22 H22 117.4 . . ?
C24 C23 C22 116.8(10) . . ?
C24 C23 C13 122.3(11) . . ?
C22 C23 C13 120.7(10) . . ?
C23 C24 C25 120.3(11) . . ?
C23 C24 H24 119.8 . . ?
C25 C24 H24 119.8 . . ?
C26 C25 C24 118.1(11) . . ?
C26 C25 H25 121.0 . . ?
C24 C25 H25 121.0 . . ?
N21 C26 C25 124.2(10) . . ?
N21 C26 H26 117.9 . . ?
C25 C26 H26 117.9 . . ?
C36 N31 C32 117.9(10) . . ?
N31 C32 C33 124.0(11) . . ?
N31 C32 H32 118.0 . . ?
C33 C32 H32 118.0 . . ?
C32 C33 C34 118.4(10) . . ?
C32 C33 C43 121.6(10) . . ?
C34 C33 C43 120.0(10) . . ?
C35 C34 C33 116.3(10) . . ?
C35 C34 H34 121.8 . . ?
C33 C34 H34 121.8 . . ?
O35 C35 C36 116.8(10) . . ?
O35 C35 C34 123.5(10) . . ?
C36 C35 C34 119.7(11) . . ?
C35 O35 C37 118.1(9) . . ?
O35 C37 H37A 109.5 . . ?
O35 C37 H37B 109.5 . . ?
H37A C37 H37B 109.5 . . ?
O35 C37 H37C 109.5 . . ?
H37A C37 H37C 109.5 . . ?
H37B C37 H37C 109.5 . . ?
N31 C36 C35 123.5(12) . . ?
N31 C36 H36 118.2 . . ?
C35 C36 H36 118.2 . . ?
C42 N41 C46 117.2(10) . . ?
N41 C42 C43 125.2(11) . . ?
N41 C42 H42 117.4 . . ?
C43 C42 H42 117.4 . . ?
C44 C43 C42 115.1(11) . . ?
C44 C43 C33 121.3(11) . . ?
C42 C43 C33 123.6(11) . . ?
C45 C44 C43 121.4(11) . . ?
C45 C44 H44 119.3 . . ?
C43 C44 H44 119.3 . . ?
C46 C45 C44 117.6(11) . . ?
C46 C45 H45 121.2 . . ?
C44 C45 H45 121.2 . . ?
N41 C46 C45 123.5(11) . . ?
N41 C46 H46 118.3 . . ?
C45 C46 H46 118.3 . . ?
C52 C51 C56 118.2(11) . . ?
C52 C51 I51 120.0(9) . . ?
C56 C51 I51 121.7(7) . . ?
F52 C52 C51 121.9(12) . . ?
F52 C52 C53 117.2(10) . . ?
C51 C52 C53 120.9(11) . . ?
F53 C53 C54 120.7(11) . . ?
F53 C53 C52 118.8(11) . . ?
C54 C53 C52 120.4(11) . . ?
C53 C54 C55 119.0(11) . . ?
C53 C54 I54 119.2(9) . . ?
C55 C54 I54 121.8(9) . . ?
F55 C55 C56 119.2(10) . . ?
F55 C55 C54 120.9(11) . . ?
C56 C55 C54 120.0(10) . . ?
F56 C56 C55 118.9(10) . . ?
F56 C56 C51 119.5(10) . . ?
C55 C56 C51 121.6(10) . . ?
C62 C61 C66 119.7(10) . . ?
C62 C61 I61 119.2(8) . . ?
C66 C61 I61 121.1(8) . . ?
F62 C62 C61 122.0(10) . . ?
F62 C62 C63 118.5(10) . . ?
C61 C62 C63 119.5(11) . . ?
F63 C63 C64 120.6(11) . . ?
F63 C63 C62 117.9(11) . . ?
C64 C63 C62 121.4(10) . . ?
C65 C64 C63 117.6(10) . . ?
C65 C64 I64 123.8(9) . . ?
C63 C64 I64 118.7(8) . . ?
C64 C65 F65 121.4(10) . . ?
C64 C65 C66 123.2(10) . . ?
F65 C65 C66 115.4(10) . . ?
F66 C66 C61 121.1(10) . . ?
F66 C66 C65 120.3(9) . . ?
C61 C66 C65 118.6(10) . . ?
C72 C71 C76 118.6(10) . . ?
C72 C71 I71 121.5(8) . . ?
C76 C71 I71 119.9(9) . . ?
C71 C72 F72 122.1(10) . . ?
C71 C72 C76 121.1(11) . 2_565 ?
F72 C72 C76 116.9(12) . 2_565 ?
F76 C76 C71 121.2(10) . . ?
F76 C76 C72 118.4(10) . 2_565 ?
C71 C76 C72 120.3(11) . 2_565 ?
C86 C81 C82 116.8(10) . . ?
C86 C81 I81 120.7(9) . . ?
C82 C81 I81 122.4(8) . . ?
F82 C82 C86 119.3(11) . 2_656 ?
F82 C82 C81 119.3(10) . . ?
C86 C82 C81 121.4(11) 2_656 . ?
F86 C86 C81 120.9(10) . . ?
F86 C86 C82 117.3(11) . 2_656 ?
C81 C86 C82 121.7(11) . 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 -0.4(19) . . . . ?
N11 C12 C13 C14 0.5(18) . . . . ?
N11 C12 C13 C23 178.7(11) . . . . ?
C12 C13 C14 C15 -0.7(17) . . . . ?
C23 C13 C14 C15 -178.9(10) . . . . ?
C13 C14 C15 O15 -178.1(11) . . . . ?
C13 C14 C15 C16 0.9(18) . . . . ?
C16 C15 O15 C17 -168.8(11) . . . . ?
C14 C15 O15 C17 10.2(17) . . . . ?
C12 N11 C16 C15 0.5(19) . . . . ?
O15 C15 C16 N11 178.3(11) . . . . ?
C14 C15 C16 N11 -1(2) . . . . ?
C26 N21 C22 C23 4.7(19) . . . . ?
N21 C22 C23 C24 -1.1(19) . . . . ?
N21 C22 C23 C13 -177.6(12) . . . . ?
C12 C13 C23 C24 -24.9(18) . . . . ?
C14 C13 C23 C24 153.2(12) . . . . ?
C12 C13 C23 C22 151.4(12) . . . . ?
C14 C13 C23 C22 -30.5(17) . . . . ?
C22 C23 C24 C25 -1.6(19) . . . . ?
C13 C23 C24 C25 174.8(12) . . . . ?
C23 C24 C25 C26 0.4(19) . . . . ?
C22 N21 C26 C25 -6.0(18) . . . . ?
C24 C25 C26 N21 4(2) . . . . ?
C36 N31 C32 C33 -6(2) . . . . ?
N31 C32 C33 C34 4(2) . . . . ?
N31 C32 C33 C43 -175.5(12) . . . . ?
C32 C33 C34 C35 -0.1(18) . . . . ?
C43 C33 C34 C35 179.0(11) . . . . ?
C33 C34 C35 O35 178.6(11) . . . . ?
C33 C34 C35 C36 -1.0(18) . . . . ?
C36 C35 O35 C37 172.1(12) . . . . ?
C34 C35 O35 C37 -7.5(18) . . . . ?
C32 N31 C36 C35 5(2) . . . . ?
O35 C35 C36 N31 179.0(12) . . . . ?
C34 C35 C36 N31 -1(2) . . . . ?
C46 N41 C42 C43 -1(2) . . . . ?
N41 C42 C43 C44 -0.8(19) . . . . ?
N41 C42 C43 C33 178.1(12) . . . . ?
C32 C33 C43 C44 29.3(19) . . . . ?
C34 C33 C43 C44 -149.7(13) . . . . ?
C32 C33 C43 C42 -149.5(13) . . . . ?
C34 C33 C43 C42 31.4(19) . . . . ?
C42 C43 C44 C45 2.1(19) . . . . ?
C33 C43 C44 C45 -176.9(12) . . . . ?
C43 C44 C45 C46 -2(2) . . . . ?
C42 N41 C46 C45 1(2) . . . . ?
C44 C45 C46 N41 0(2) . . . . ?
C56 C51 C52 F52 179.4(11) . . . . ?
I51 C51 C52 F52 3.8(17) . . . . ?
C56 C51 C52 C53 0.6(19) . . . . ?
I51 C51 C52 C53 -175.0(10) . . . . ?
F52 C52 C53 F53 2.5(18) . . . . ?
C51 C52 C53 F53 -178.5(12) . . . . ?
F52 C52 C53 C54 179.2(12) . . . . ?
C51 C52 C53 C54 -2(2) . . . . ?
F53 C53 C54 C55 178.9(12) . . . . ?
C52 C53 C54 C55 2(2) . . . . ?
F53 C53 C54 I54 -3.6(18) . . . . ?
C52 C53 C54 I54 179.8(10) . . . . ?
C53 C54 C55 F55 -179.2(11) . . . . ?
I54 C54 C55 F55 3.4(17) . . . . ?
C53 C54 C55 C56 -1(2) . . . . ?
I54 C54 C55 C56 -178.9(9) . . . . ?
F55 C55 C56 F56 -1.1(17) . . . . ?
C54 C55 C56 F56 -178.8(11) . . . . ?
F55 C55 C56 C51 178.0(11) . . . . ?
C54 C55 C56 C51 0.2(19) . . . . ?
C52 C51 C56 F56 179.3(11) . . . . ?
I51 C51 C56 F56 -5.2(16) . . . . ?
C52 C51 C56 C55 0.2(19) . . . . ?
I51 C51 C56 C55 175.7(9) . . . . ?
C66 C61 C62 F62 -179.4(11) . . . . ?
I61 C61 C62 F62 1.8(17) . . . . ?
C66 C61 C62 C63 0.7(19) . . . . ?
I61 C61 C62 C63 -178.1(9) . . . . ?
F62 C62 C63 F63 -1.3(18) . . . . ?
C61 C62 C63 F63 178.6(11) . . . . ?
F62 C62 C63 C64 -180.0(11) . . . . ?
C61 C62 C63 C64 -0.1(19) . . . . ?
F63 C63 C64 C65 179.7(12) . . . . ?
C62 C63 C64 C65 -2(2) . . . . ?
F63 C63 C64 I64 0.8(17) . . . . ?
C62 C63 C64 I64 179.4(9) . . . . ?
C63 C64 C65 F65 -178.1(11) . . . . ?
I64 C64 C65 F65 0.7(18) . . . . ?
C63 C64 C65 C66 3(2) . . . . ?
I64 C64 C65 C66 -178.2(9) . . . . ?
C62 C61 C66 F66 179.1(11) . . . . ?
I61 C61 C66 F66 -2.2(16) . . . . ?
C62 C61 C66 C65 0.4(18) . . . . ?
I61 C61 C66 C65 179.2(9) . . . . ?
C64 C65 C66 F66 179.0(12) . . . . ?
F65 C65 C66 F66 0.0(16) . . . . ?
C64 C65 C66 C61 -2.4(19) . . . . ?
F65 C65 C66 C61 178.7(11) . . . . ?
C76 C71 C72 F72 179.4(11) . . . . ?
I71 C71 C72 F72 -2.1(16) . . . . ?
C76 C71 C72 C76 -1.3(19) . . . 2_565 ?
I71 C71 C72 C76 177.2(9) . . . 2_565 ?
C72 C71 C76 F76 177.5(10) . . . . ?
I71 C71 C76 F76 -1.0(15) . . . . ?
C72 C71 C76 C72 1.3(19) . . . 2_565 ?
I71 C71 C76 C72 -177.2(9) . . . 2_565 ?
C86 C81 C82 F82 179.8(10) . . . . ?
I81 C81 C82 F82 0.9(16) . . . . ?
C86 C81 C82 C86 1.5(19) . . . 2_656 ?
I81 C81 C82 C86 -177.4(9) . . . 2_656 ?
C82 C81 C86 F86 -177.5(10) . . . . ?
I81 C81 C86 F86 1.4(16) . . . . ?
C82 C81 C86 C82 -1.5(19) . . . 2_656 ?
I81 C81 C86 C82 177.4(9) . . . 2_656 ?

_diffrn_measured_fraction_theta_max 0.947
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         1.885
_refine_diff_density_min         -1.994
_refine_diff_density_rms         0.338

#END

data_A7
_database_code_depnum_ccdc_archive 'CCDC 694677'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
(pyridine-3,5-COOH) (2-AcNH-pyr)2, (1,4-I2-F4-benzene)2
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         
;
(C7 H5 N O4) (C7 H8 N2 O)2 (C6 F4 I2)2
;
_chemical_formula_sum            'C33 H21 F8 I4 N5 O6'
_chemical_formula_weight         1243.15

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           Orthorhombic
_symmetry_space_group_name_H-M   P2(1)2(1)2

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

_cell_length_a                   30.345(2)
_cell_length_b                   4.1878(3)
_cell_length_c                   16.6946(12)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2121.5(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    6219
_cell_measurement_theta_min      2.35
_cell_measurement_theta_max      24.40

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.946
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1172
_exptl_absorpt_coefficient_mu    3.018
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.605
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      173(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            27677
_diffrn_reflns_av_R_equivalents  0.1209
_diffrn_reflns_av_sigmaI/netI    0.0834
_diffrn_reflns_limit_h_min       -39
_diffrn_reflns_limit_h_max       39
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         1.81
_diffrn_reflns_theta_max         27.86
_reflns_number_total             5003
_reflns_number_gt                3336
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker XSCANS'
_computing_cell_refinement       'Bruker XSCANS'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_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)+(0.0600P)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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.07(5)
_refine_ls_number_reflns         5003
_refine_ls_number_parameters     254
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0845
_refine_ls_R_factor_gt           0.0427
_refine_ls_wR_factor_ref         0.1235
_refine_ls_wR_factor_gt          0.1067
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_restrained_S_all      1.013
_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
C11 C 0.3271(2) 1.234(2) 0.1467(4) 0.0307(16) Uani 1 1 d . . .
I11 I 0.278935(16) 1.00894(14) 0.21461(3) 0.03755(15) Uani 1 1 d . . .
C12 C 0.3191(3) 1.323(2) 0.0683(5) 0.040(2) Uani 1 1 d . . .
F12 F 0.28080(18) 1.253(2) 0.0353(3) 0.0749(19) Uani 1 1 d . . .
C13 C 0.3504(3) 1.477(3) 0.0238(5) 0.043(2) Uani 1 1 d . . .
F13 F 0.3412(2) 1.559(2) -0.0506(3) 0.076(2) Uani 1 1 d . . .
C14 C 0.3908(3) 1.5508(19) 0.0551(5) 0.037(2) Uani 1 1 d . . .
I14 I 0.439456(19) 1.76156(15) -0.01412(3) 0.04563(17) Uani 1 1 d . . .
C15 C 0.3987(3) 1.459(3) 0.1343(5) 0.048(2) Uani 1 1 d . . .
F15 F 0.43796(18) 1.524(2) 0.1674(3) 0.085(2) Uani 1 1 d . . .
C16 C 0.3675(3) 1.299(3) 0.1777(5) 0.043(2) Uani 1 1 d . . .
F16 F 0.37728(18) 1.225(2) 0.2538(3) 0.0733(19) Uani 1 1 d . . .
N21 N 0.0000 -0.5000 0.1529(5) 0.039(2) Uani 1 2 d S . .
C22 C 0.0297(3) -0.3430(19) 0.1937(5) 0.036(2) Uani 1 1 d . . .
H22 H 0.0519 -0.2308 0.1649 0.043 Uiso 1 1 calc R . .
C23 C 0.0308(3) -0.3312(18) 0.2774(5) 0.0327(19) Uani 1 1 d . . .
C27 C 0.0665(3) -0.138(2) 0.3165(5) 0.0361(19) Uani 1 1 d . . .
O21 O 0.0658(2) -0.1397(16) 0.3927(3) 0.0506(18) Uani 1 1 d . . .
H21 H 0.0895 -0.0626 0.4104 0.061 Uiso 1 1 calc R . .
O22 O 0.09280(17) 0.0131(18) 0.2749(3) 0.0424(13) Uani 1 1 d . . .
C24 C 0.0000 -0.5000 0.3190(6) 0.030(2) Uani 1 2 d S . .
H24 H 0.0000 -0.5000 0.3759 0.037 Uiso 1 2 calc SR . .
N31 N 0.1300(2) 0.1754(17) 0.4596(4) 0.0379(17) Uani 1 1 d . . .
C32 C 0.1613(3) 0.342(2) 0.4276(5) 0.038(2) Uani 1 1 d . . .
N32 N 0.1576(2) 0.3791(16) 0.3461(4) 0.0367(17) Uani 1 1 d . . .
H32 H 0.1356 0.2761 0.3234 0.044 Uiso 1 1 calc R . .
C33 C 0.1955(3) 0.474(3) 0.4733(5) 0.0418(19) Uani 1 1 d . . .
H33 H 0.2181 0.5980 0.4490 0.050 Uiso 1 1 calc R . .
C34 C 0.1951(3) 0.419(3) 0.5538(6) 0.054(3) Uani 1 1 d . . .
H34 H 0.2178 0.5053 0.5867 0.065 Uiso 1 1 calc R . .
C35 C 0.1620(3) 0.240(3) 0.5877(5) 0.052(2) Uani 1 1 d . . .
H35 H 0.1612 0.2013 0.6437 0.062 Uiso 1 1 calc R . .
C36 C 0.1308(3) 0.120(2) 0.5390(6) 0.049(2) Uani 1 1 d . . .
H36 H 0.1083 -0.0093 0.5617 0.058 Uiso 1 1 calc R . .
C37 C 0.1838(3) 0.558(2) 0.2946(5) 0.038(2) Uani 1 1 d . . .
O37 O 0.21443(19) 0.7227(18) 0.3184(3) 0.0477(15) Uani 1 1 d . . .
C38 C 0.1693(3) 0.535(3) 0.2076(5) 0.048(2) Uani 1 1 d . . .
H38A H 0.1888 0.6666 0.1743 0.072 Uiso 1 1 calc R . .
H38B H 0.1389 0.6129 0.2026 0.072 Uiso 1 1 calc R . .
H38C H 0.1708 0.3127 0.1898 0.072 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C11 C16 1.358(11) . ?
C11 C12 1.383(11) . ?
C11 I11 2.076(8) . ?
C12 F12 1.320(9) . ?
C12 C13 1.365(12) . ?
C13 F13 1.318(9) . ?
C13 C14 1.368(12) . ?
C14 C15 1.398(12) . ?
C14 I14 2.073(8) . ?
C15 F15 1.341(10) . ?
C15 C16 1.366(12) . ?
C16 F16 1.341(9) . ?
N21 C22 1.308(9) . ?
N21 C22 1.308(9) 2_545 ?
C22 C23 1.398(11) . ?
C22 H22 0.9500 . ?
C23 C24 1.362(10) . ?
C23 C27 1.502(12) . ?
C27 O22 1.232(10) . ?
C27 O21 1.273(9) . ?
O21 H21 0.8400 . ?
C24 C23 1.362(10) 2_545 ?
C24 H24 0.9500 . ?
N31 C32 1.293(11) . ?
N31 C36 1.345(11) . ?
C32 N32 1.375(11) . ?
C32 C33 1.402(12) . ?
N32 C37 1.390(10) . ?
N32 H32 0.8800 . ?
C33 C34 1.365(12) . ?
C33 H33 0.9500 . ?
C34 C35 1.376(13) . ?
C34 H34 0.9500 . ?
C35 C36 1.344(13) . ?
C35 H35 0.9500 . ?
C36 H36 0.9500 . ?
C37 O37 1.224(10) . ?
C37 C38 1.521(12) . ?
C38 H38A 0.9800 . ?
C38 H38B 0.9800 . ?
C38 H38C 0.9800 . ?

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 C11 C12 117.6(7) . . ?
C16 C11 I11 121.3(6) . . ?
C12 C11 I11 121.1(6) . . ?
F12 C12 C13 119.3(7) . . ?
F12 C12 C11 119.2(7) . . ?
C13 C12 C11 121.4(7) . . ?
F13 C13 C12 119.3(8) . . ?
F13 C13 C14 119.3(8) . . ?
C12 C13 C14 121.4(7) . . ?
C13 C14 C15 116.9(8) . . ?
C13 C14 I14 121.5(6) . . ?
C15 C14 I14 121.5(6) . . ?
F15 C15 C16 119.8(8) . . ?
F15 C15 C14 119.1(8) . . ?
C16 C15 C14 121.1(8) . . ?
F16 C16 C11 120.9(7) . . ?
F16 C16 C15 117.5(8) . . ?
C11 C16 C15 121.5(8) . . ?
C22 N21 C22 117.3(10) . 2_545 ?
N21 C22 C23 123.6(8) . . ?
N21 C22 H22 118.2 . . ?
C23 C22 H22 118.2 . . ?
C24 C23 C22 118.4(8) . . ?
C24 C23 C27 123.6(8) . . ?
C22 C23 C27 118.0(7) . . ?
O22 C27 O21 125.3(8) . . ?
O22 C27 C23 119.9(7) . . ?
O21 C27 C23 114.8(8) . . ?
C27 O21 H21 109.5 . . ?
C23 C24 C23 118.7(10) 2_545 . ?
C23 C24 H24 120.7 2_545 . ?
C23 C24 H24 120.7 . . ?
C32 N31 C36 119.1(8) . . ?
N31 C32 N32 114.2(7) . . ?
N31 C32 C33 122.1(8) . . ?
N32 C32 C33 123.6(8) . . ?
C32 N32 C37 128.8(7) . . ?
C32 N32 H32 115.6 . . ?
C37 N32 H32 115.6 . . ?
C34 C33 C32 117.6(9) . . ?
C34 C33 H33 121.2 . . ?
C32 C33 H33 121.2 . . ?
C33 C34 C35 120.2(9) . . ?
C33 C34 H34 119.9 . . ?
C35 C34 H34 119.9 . . ?
C36 C35 C34 118.0(8) . . ?
C36 C35 H35 121.0 . . ?
C34 C35 H35 121.0 . . ?
C35 C36 N31 123.0(9) . . ?
C35 C36 H36 118.5 . . ?
N31 C36 H36 118.5 . . ?
O37 C37 N32 122.6(8) . . ?
O37 C37 C38 124.3(8) . . ?
N32 C37 C38 113.0(8) . . ?
C37 C38 H38A 109.5 . . ?
C37 C38 H38B 109.5 . . ?
H38A C38 H38B 109.5 . . ?
C37 C38 H38C 109.5 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 109.5 . . ?

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 C11 C12 F12 177.5(9) . . . . ?
I11 C11 C12 F12 -2.6(13) . . . . ?
C16 C11 C12 C13 -1.1(15) . . . . ?
I11 C11 C12 C13 178.7(7) . . . . ?
F12 C12 C13 F13 1.5(15) . . . . ?
C11 C12 C13 F13 -179.8(10) . . . . ?
F12 C12 C13 C14 -179.1(9) . . . . ?
C11 C12 C13 C14 -0.4(15) . . . . ?
F13 C13 C14 C15 179.9(9) . . . . ?
C12 C13 C14 C15 0.5(15) . . . . ?
F13 C13 C14 I14 -4.0(14) . . . . ?
C12 C13 C14 I14 176.6(7) . . . . ?
C13 C14 C15 F15 179.5(9) . . . . ?
I14 C14 C15 F15 3.4(14) . . . . ?
C13 C14 C15 C16 1.0(15) . . . . ?
I14 C14 C15 C16 -175.1(8) . . . . ?
C12 C11 C16 F16 178.6(10) . . . . ?
I11 C11 C16 F16 -1.2(14) . . . . ?
C12 C11 C16 C15 2.6(15) . . . . ?
I11 C11 C16 C15 -177.2(8) . . . . ?
F15 C15 C16 F16 2.7(16) . . . . ?
C14 C15 C16 F16 -178.7(9) . . . . ?
F15 C15 C16 C11 178.9(10) . . . . ?
C14 C15 C16 C11 -2.6(16) . . . . ?
C22 N21 C22 C23 -1.1(6) 2_545 . . . ?
N21 C22 C23 C24 2.1(11) . . . . ?
N21 C22 C23 C27 -179.2(6) . . . . ?
C24 C23 C27 O22 -178.8(7) . . . . ?
C22 C23 C27 O22 2.5(11) . . . . ?
C24 C23 C27 O21 -0.7(11) . . . . ?
C22 C23 C27 O21 -179.4(7) . . . . ?
C22 C23 C24 C23 -0.9(5) . . . 2_545 ?
C27 C23 C24 C23 -179.6(8) . . . 2_545 ?
C36 N31 C32 N32 179.0(8) . . . . ?
C36 N31 C32 C33 -1.8(13) . . . . ?
N31 C32 N32 C37 175.9(8) . . . . ?
C33 C32 N32 C37 -3.3(14) . . . . ?
N31 C32 C33 C34 0.7(14) . . . . ?
N32 C32 C33 C34 179.8(9) . . . . ?
C32 C33 C34 C35 0.0(15) . . . . ?
C33 C34 C35 C36 0.6(16) . . . . ?
C34 C35 C36 N31 -1.8(17) . . . . ?
C32 N31 C36 C35 2.4(15) . . . . ?
C32 N32 C37 O37 -3.0(13) . . . . ?
C32 N32 C37 C38 179.4(8) . . . . ?

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
O21 H21 N31 0.84 1.78 2.604(9) 164.8 .
N32 H32 O22 0.88 1.89 2.761(9) 173.3 .

_diffrn_measured_fraction_theta_max 0.989
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         1.037
_refine_diff_density_min         -0.938
_refine_diff_density_rms         0.169


