# Supplementary Material (ESI) for Chemical Communications
# This journal is © The Royal Society of Chemistry 2006

data_global
_journal_name_full               Chem.Commun.

_journal_coden_Cambridge         0182

_publ_contact_author_name        'Giuseppe Resnati'
_publ_contact_author_address     
;
Dipartimento di Chimica
Politecnico di Milano
7, via Mancinelli
Milano
I-20131
ITALY
;

_publ_contact_author_email       GIUSEPPE.RESNATI@POLIMI.IT

_publ_section_title              
;
Metric engineering of supramolecular borromean rings
;
loop_
_publ_author_name
'Giuseppe Resnati'
'Rosalba Liantonio'
'Pierangelo Metrangolo'
'Franck Meyer'
'Tullio Pilati'

# Attachment 'Complex 4a.CIF'

data_re168
_database_code_depnum_ccdc_archive 'CCDC 290598'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C18 H36 K N2 O6) +1, 3(C2 F4 I2), 2I -1'
_chemical_formula_sum            'C42 H72 F12 I8 K2 N4 O12'
_chemical_formula_weight         2146.44

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'
K K 0.2009 0.2494 '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           trigonal
_symmetry_space_group_name_H-M   R-3c
_symmetry_space_group_name_Hall  '-R 3 2"c'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'y, x, -z+1/2'
'x-y, -y, -z+1/2'
'-x, -x+y, -z+1/2'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'y+2/3, x+1/3, -z+5/6'
'x-y+2/3, -y+1/3, -z+5/6'
'-x+2/3, -x+y+1/3, -z+5/6'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'y+1/3, x+2/3, -z+7/6'
'x-y+1/3, -y+2/3, -z+7/6'
'-x+1/3, -x+y+2/3, -z+7/6'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'-y, -x, z-1/2'
'-x+y, y, z-1/2'
'x, x-y, z-1/2'
'-x+2/3, -y+1/3, -z+1/3'
'y+2/3, -x+y+1/3, -z+1/3'
'x-y+2/3, x+1/3, -z+1/3'
'-y+2/3, -x+1/3, z-1/6'
'-x+y+2/3, y+1/3, z-1/6'
'x+2/3, x-y+1/3, z-1/6'
'-x+1/3, -y+2/3, -z+2/3'
'y+1/3, -x+y+2/3, -z+2/3'
'x-y+1/3, x+2/3, -z+2/3'
'-y+1/3, -x+2/3, z+1/6'
'-x+y+1/3, y+2/3, z+1/6'
'x+1/3, x-y+2/3, z+1/6'

_cell_length_a                   11.7478(15)
_cell_length_b                   11.7478(15)
_cell_length_c                   85.034(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                120.00
_cell_volume                     10163(2)
_cell_formula_units_Z            6
_cell_measurement_temperature    90(2)
_cell_measurement_reflns_used    29749
_cell_measurement_theta_min      2.219
_cell_measurement_theta_max      35.960

_exptl_crystal_description       'elongated prism'
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.104
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             6108
_exptl_absorpt_coefficient_mu    3.870
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS,(Bruker, 1997)'
_exptl_absorpt_correction_T_min  0.626845
_exptl_absorpt_correction_T_max  1.000000

_exptl_special_details           
;
Low temperature Bruker KRIOFLEX device.
;

_diffrn_ambient_temperature      90(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker SMART APEX'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_standards_decay_%        0.0
_diffrn_reflns_number            91069
_diffrn_reflns_av_R_equivalents  0.0278
_diffrn_reflns_av_sigmaI/netI    0.0253
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -142
_diffrn_reflns_limit_l_max       142
_diffrn_reflns_theta_min         2.22
_diffrn_reflns_theta_max         36.76
_reflns_number_total             5274
_reflns_number_gt                4536
_reflns_threshold_expression     >2\s(I)

_computing_data_collection       'SMART (Bruker, 1999)'
_computing_cell_refinement       'SAINT (Bruker, 1999)'
_computing_data_reduction        'SAINT (Bruker, 1999)'
_computing_structure_solution    'SIR-92 (Altomare et al., 1994)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    
'ORTEP-III (Burnett and Johnson, 1996), Mercury 1.4, CCDC'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.

Disordered C2F4 group and H atoms were refined with soft restraints.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[\s^2^(Fo^2^)+(0.0422P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5274
_refine_ls_number_parameters     178
_refine_ls_number_restraints     107
_refine_ls_R_factor_all          0.0354
_refine_ls_R_factor_gt           0.0285
_refine_ls_wR_factor_ref         0.0690
_refine_ls_wR_factor_gt          0.0672
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.046
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
I2 I 0.0000 0.0000 0.026662(2) 0.01369(4) Uani 1 3 d S . .
I1 I 0.052308(12) -0.169575(11) 0.056409(1) 0.01986(4) Uani 1 1 d D . .
C7 C 0.0949(5) -0.2638(5) 0.07566(4) 0.0246(11) Uani 0.50 1 d PDU . .
F1 F 0.2123(8) -0.2505(10) 0.07298(5) 0.079(2) Uani 0.50 1 d PDU . .
F2 F 0.0115(7) -0.3913(4) 0.07633(6) 0.091(2) Uani 0.50 1 d PDU . .
C8 C 0.0985(6) -0.2023(5) 0.09145(4) 0.0246(11) Uani 0.50 1 d PD . .
F3 F -0.0214(7) -0.2270(9) 0.09431(5) 0.080(3) Uani 0.50 1 d PD . .
F4 F 0.1749(7) -0.0748(3) 0.09029(6) 0.078(2) Uani 0.50 1 d PD . .
K K 0.6667 0.3333 0.013744(7) 0.01292(9) Uani 1 3 d S . .
N1 N 0.6667 0.3333 -0.02084(3) 0.0129(4) Uani 1 3 d S . .
C1 C 0.74634(16) 0.46987(15) -0.026281(18) 0.0149(3) Uani 1 1 d D . .
H1A H 0.736(2) 0.476(3) -0.03769(17) 0.018 Uiso 1 1 d D . .
H1B H 0.8387(15) 0.496(2) -0.0247(3) 0.018 Uiso 1 1 d D . .
C2 C 0.72008(16) 0.56657(16) -0.01744(2) 0.0159(3) Uani 1 1 d D . .
H2A H 0.7833(18) 0.6587(16) -0.0202(3) 0.019 Uiso 1 1 d D . .
H2B H 0.6319(15) 0.552(2) -0.0197(3) 0.019 Uiso 1 1 d D . .
O1 O 0.74287(12) 0.55997(11) -0.001111(14) 0.0143(2) Uani 1 1 d . . .
C3 C 0.73467(17) 0.65950(15) 0.007558(19) 0.0163(3) Uani 1 1 d D . .
H3A H 0.6552(15) 0.661(2) 0.0041(3) 0.020 Uiso 1 1 d D . .
H3B H 0.8072(17) 0.7467(17) 0.0043(3) 0.020 Uiso 1 1 d D . .
C4 C 0.73679(16) 0.63322(16) 0.024912(19) 0.0173(3) Uani 1 1 d D . .
H4A H 0.8158(19) 0.628(2) 0.0276(3) 0.021 Uiso 1 1 d D . .
H4B H 0.745(2) 0.710(2) 0.0305(3) 0.021 Uiso 1 1 d D . .
O2 O 0.61858(12) 0.51480(12) 0.028736(15) 0.0159(2) Uani 1 1 d . . .
C5 C 0.59067(18) 0.49676(17) 0.04520(2) 0.0181(3) Uani 1 1 d D . .
H5A H 0.4975(15) 0.4307(18) 0.0462(3) 0.022 Uiso 1 1 d D . .
H5B H 0.603(2) 0.5788(16) 0.0496(3) 0.022 Uiso 1 1 d D . .
C6 C 0.67672(17) 0.45678(17) 0.05435(2) 0.0181(3) Uani 1 1 d D . .
H6A H 0.7678(16) 0.527(2) 0.0531(3) 0.022 Uiso 1 1 d D . .
H6B H 0.656(2) 0.450(2) 0.06568(17) 0.022 Uiso 1 1 d D . .
N2 N 0.6667 0.3333 0.04885(3) 0.0154(4) Uani 1 3 d S . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
I2 0.01403(5) 0.01403(5) 0.01301(7) 0.000 0.000 0.00701(3)
I1 0.02701(6) 0.02324(6) 0.01508(6) 0.00111(3) -0.00089(4) 0.01689(5)
C7 0.039(3) 0.025(2) 0.0186(8) -0.0028(9) -0.0054(10) 0.023(3)
F1 0.106(5) 0.190(7) 0.0230(18) 0.032(4) 0.024(3) 0.135(5)
F2 0.169(6) 0.0158(13) 0.061(3) -0.0077(16) -0.076(3) 0.026(3)
C8 0.039(3) 0.025(2) 0.0186(8) -0.0028(9) -0.0054(10) 0.023(3)
F3 0.088(5) 0.189(8) 0.032(2) 0.033(4) 0.024(3) 0.121(6)
F4 0.148(5) 0.0168(14) 0.059(3) -0.0131(15) -0.068(3) 0.033(2)
K 0.01185(13) 0.01185(13) 0.0151(2) 0.000 0.000 0.00593(7)
N1 0.0113(6) 0.0113(6) 0.0162(10) 0.000 0.000 0.0057(3)
C1 0.0159(6) 0.0114(6) 0.0162(6) 0.0012(5) 0.0017(5) 0.0060(5)
C2 0.0177(7) 0.0135(6) 0.0167(7) 0.0002(5) -0.0014(5) 0.0080(5)
O1 0.0167(5) 0.0123(5) 0.0155(5) 0.0002(4) 0.0000(4) 0.0086(4)
C3 0.0196(7) 0.0120(6) 0.0187(6) -0.0006(5) 0.0009(5) 0.0088(6)
C4 0.0164(7) 0.0141(6) 0.0193(7) -0.0021(5) 0.0004(5) 0.0061(6)
O2 0.0159(5) 0.0139(5) 0.0167(5) -0.0001(4) 0.0011(4) 0.0065(4)
C5 0.0196(7) 0.0193(7) 0.0178(7) -0.0004(5) 0.0032(5) 0.0116(6)
C6 0.0202(7) 0.0171(7) 0.0172(7) -0.0020(5) -0.0012(5) 0.0094(6)
N2 0.0147(6) 0.0147(6) 0.0169(10) 0.000 0.000 0.0074(3)

_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 C7 2.170(2) . ?
I1 C8 2.171(2) 16_544 ?
C7 F2 1.318(6) . ?
C7 F1 1.328(6) . ?
C7 C8 1.516(5) . ?
C8 F4 1.309(7) . ?
C8 F3 1.311(7) . ?
C8 I1 2.170(2) 16_544 ?
K O1 2.6650(12) 3_665 ?
K O1 2.6650(12) 2_655 ?
K O1 2.6650(12) . ?
K O2 2.7737(13) 3_665 ?
K O2 2.7737(13) 2_655 ?
K O2 2.7737(13) . ?
K N1 2.941(2) . ?
K N2 2.985(3) . ?
K C4 3.3301(17) 3_665 ?
K C4 3.3301(17) 2_655 ?
K C4 3.3301(17) . ?
N1 C1 1.4701(17) 3_665 ?
N1 C1 1.4701(17) . ?
N1 C1 1.4701(17) 2_655 ?
C1 C2 1.517(2) . ?
C1 H1A 0.986(13) . ?
C1 H1B 0.977(14) . ?
C2 O1 1.424(2) . ?
C2 H2A 0.987(14) . ?
C2 H2B 0.981(14) . ?
O1 C3 1.4257(19) . ?
C3 C4 1.510(2) . ?
C3 H3A 0.987(14) . ?
C3 H3B 0.990(14) . ?
C4 O2 1.427(2) . ?
C4 H4A 0.988(14) . ?
C4 H4B 0.978(14) . ?
O2 C5 1.429(2) . ?
C5 C6 1.524(3) . ?
C5 H5A 0.979(14) . ?
C5 H5B 0.973(14) . ?
C6 N2 1.4712(19) . ?
C6 H6A 0.976(14) . ?
C6 H6B 0.986(13) . ?
N2 C6 1.4712(19) 3_665 ?
N2 C6 1.4712(19) 2_655 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
F2 C7 F1 106.3(6) . . ?
F2 C7 C8 109.3(5) . . ?
F1 C7 C8 108.4(6) . . ?
F2 C7 I1 112.5(3) . . ?
F1 C7 I1 107.5(3) . . ?
C8 C7 I1 112.5(3) . . ?
F4 C8 F3 108.2(5) . . ?
F4 C8 C7 108.6(6) . . ?
F3 C8 C7 106.8(5) . . ?
F4 C8 I1 110.9(3) . 16_544 ?
F3 C8 I1 109.8(3) . 16_544 ?
C7 C8 I1 112.4(2) . 16_544 ?
O1 K O1 99.38(4) 3_665 2_655 ?
O1 K O1 99.38(4) 3_665 . ?
O1 K O1 99.38(4) 2_655 . ?
O1 K O2 62.98(4) 3_665 3_665 ?
O1 K O2 154.18(4) 2_655 3_665 ?
O1 K O2 101.98(4) . 3_665 ?
O1 K O2 101.98(4) 3_665 2_655 ?
O1 K O2 62.98(4) 2_655 2_655 ?
O1 K O2 154.18(4) . 2_655 ?
O2 K O2 100.55(4) 3_665 2_655 ?
O1 K O2 154.18(4) 3_665 . ?
O1 K O2 101.98(4) 2_655 . ?
O1 K O2 62.98(4) . . ?
O2 K O2 100.55(4) 3_665 . ?
O2 K O2 100.55(4) 2_655 . ?
O1 K N1 61.71(3) 3_665 . ?
O1 K N1 61.71(3) 2_655 . ?
O1 K N1 61.71(3) . . ?
O2 K N1 117.36(3) 3_665 . ?
O2 K N1 117.36(3) 2_655 . ?
O2 K N1 117.36(3) . . ?
O1 K N2 118.29(3) 3_665 . ?
O1 K N2 118.29(3) 2_655 . ?
O1 K N2 118.29(3) . . ?
O2 K N2 62.64(3) 3_665 . ?
O2 K N2 62.64(3) 2_655 . ?
O2 K N2 62.64(3) . . ?
N1 K N2 180.0 . . ?
O1 K C4 45.28(4) 3_665 3_665 ?
O1 K C4 129.47(4) 2_655 3_665 ?
O1 K C4 118.25(4) . 3_665 ?
O2 K C4 24.98(4) 3_665 3_665 ?
O2 K C4 87.27(4) 2_655 3_665 ?
O2 K C4 124.11(4) . 3_665 ?
N1 K C4 106.57(3) . 3_665 ?
N2 K C4 73.43(3) . 3_665 ?
O1 K C4 118.25(4) 3_665 2_655 ?
O1 K C4 45.28(4) 2_655 2_655 ?
O1 K C4 129.47(4) . 2_655 ?
O2 K C4 124.11(4) 3_665 2_655 ?
O2 K C4 24.98(4) 2_655 2_655 ?
O2 K C4 87.27(4) . 2_655 ?
N1 K C4 106.57(3) . 2_655 ?
N2 K C4 73.43(3) . 2_655 ?
C4 K C4 112.21(3) 3_665 2_655 ?
O1 K C4 129.47(4) 3_665 . ?
O1 K C4 118.25(4) 2_655 . ?
O1 K C4 45.28(4) . . ?
O2 K C4 87.27(4) 3_665 . ?
O2 K C4 124.11(4) 2_655 . ?
O2 K C4 24.98(4) . . ?
N1 K C4 106.57(3) . . ?
N2 K C4 73.43(3) . . ?
C4 K C4 112.21(3) 3_665 . ?
C4 K C4 112.21(3) 2_655 . ?
C1 N1 C1 110.59(10) 3_665 . ?
C1 N1 C1 110.59(10) 3_665 2_655 ?
C1 N1 C1 110.59(10) . 2_655 ?
C1 N1 K 108.33(11) 3_665 . ?
C1 N1 K 108.33(11) . . ?
C1 N1 K 108.33(11) 2_655 . ?
N1 C1 C2 113.85(13) . . ?
N1 C1 H1A 110.9(15) . . ?
C2 C1 H1A 110.4(15) . . ?
N1 C1 H1B 107.7(15) . . ?
C2 C1 H1B 107.6(15) . . ?
H1A C1 H1B 106.0(16) . . ?
O1 C2 C1 109.16(13) . . ?
O1 C2 H2A 103.4(13) . . ?
C1 C2 H2A 112.3(14) . . ?
O1 C2 H2B 113.3(14) . . ?
C1 C2 H2B 111.3(15) . . ?
H2A C2 H2B 107.1(16) . . ?
C2 O1 C3 111.59(12) . . ?
C2 O1 K 122.57(9) . . ?
C3 O1 K 116.59(9) . . ?
O1 C3 C4 108.83(13) . . ?
O1 C3 H3A 107.9(14) . . ?
C4 C3 H3A 114.2(14) . . ?
O1 C3 H3B 109.2(15) . . ?
C4 C3 H3B 113.0(14) . . ?
H3A C3 H3B 103.5(15) . . ?
O2 C4 C3 108.32(13) . . ?
O2 C4 K 55.14(8) . . ?
C3 C4 K 85.24(9) . . ?
O2 C4 H4A 111.8(14) . . ?
C3 C4 H4A 110.3(13) . . ?
K C4 H4A 74.8(13) . . ?
O2 C4 H4B 112.6(15) . . ?
C3 C4 H4B 106.7(14) . . ?
K C4 H4B 165.8(15) . . ?
H4A C4 H4B 106.9(16) . . ?
C4 O2 C5 114.01(13) . . ?
C4 O2 K 99.88(9) . . ?
C5 O2 K 117.13(9) . . ?
O2 C5 C6 114.04(14) . . ?
O2 C5 H5A 106.6(15) . . ?
C6 C5 H5A 111.2(15) . . ?
O2 C5 H5B 108.5(15) . . ?
C6 C5 H5B 108.3(15) . . ?
H5A C5 H5B 108.0(16) . . ?
N2 C6 C5 113.76(14) . . ?
N2 C6 H6A 108.1(16) . . ?
C5 C6 H6A 107.5(16) . . ?
N2 C6 H6B 109.3(16) . . ?
C5 C6 H6B 110.8(15) . . ?
H6A C6 H6B 107.0(16) . . ?
C6 N2 C6 110.39(11) 3_665 2_655 ?
C6 N2 C6 110.39(11) 3_665 . ?
C6 N2 C6 110.39(11) 2_655 . ?
C6 N2 K 108.53(11) 3_665 . ?
C6 N2 K 108.53(11) 2_655 . ?
C6 N2 K 108.53(11) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
F2 C7 C8 F4 -175.8(5) . . . . ?
F1 C7 C8 F4 68.8(6) . . . . ?
I1 C7 C8 F4 -50.1(6) . . . . ?
F2 C7 C8 F3 -59.3(7) . . . . ?
F1 C7 C8 F3 -174.8(6) . . . . ?
I1 C7 C8 F3 66.4(6) . . . . ?
F2 C7 C8 I1 61.1(6) . . . 16_544 ?
F1 C7 C8 I1 -54.3(7) . . . 16_544 ?
N1 C1 C2 O1 57.49(18) . . . . ?
C1 C2 O1 C3 173.16(13) . . . . ?
C1 C2 O1 K -41.35(16) . . . . ?
C2 O1 C3 C4 170.55(13) . . . . ?
K O1 C3 C4 22.82(16) . . . . ?
O1 C3 C4 O2 -67.00(17) . . . . ?
O1 C3 C4 K -16.17(11) . . . . ?
C3 C4 O2 C5 -163.96(13) . . . . ?
C3 C4 O2 K 70.29(13) . . . . ?
C4 O2 C5 C6 -74.63(17) . . . . ?
O2 C5 C6 N2 -59.05(19) . . . . ?
C5 C6 N2 C6 161.46(15) . . . 3_665 ?
C5 C6 N2 C6 -76.2(2) . . . 2_655 ?
C5 C6 N2 K 42.63(14) . . . . ?

_diffrn_measured_fraction_theta_max 0.930
_diffrn_reflns_theta_full        36.76
_diffrn_measured_fraction_theta_full 0.930
_refine_diff_density_max         2.394
_refine_diff_density_min         -0.805
_refine_diff_density_rms         0.157

# Attachment 'Complex 4c.CIF'

data_re144lt
_database_code_depnum_ccdc_archive 'CCDC 290599'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
2(4,7,13,16,21,24-hexaoxa-1,10-diazabicyclo[8.8.8]hexacosane.potassium iodide)
3(1,1,2,2,3,3,4,4,5,5,6,6-dodecafluoro-1,6-diiodohexane)
;
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C18 H36 K N2 O6) +1, 3(C6 F12 I2), 2I -1'
_chemical_formula_sum            'C54 H72 F36 I8 K2 N4 O12'
_chemical_formula_weight         2746.56

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'
K K 0.2009 0.2494 '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           trigonal
_symmetry_space_group_name_H-M   P-3
_symmetry_space_group_name_Hall  '-P 3'

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

_cell_length_a                   11.861(2)
_cell_length_b                   11.861(2)
_cell_length_c                   17.319(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                120.00
_cell_volume                     2110.1(6)
_cell_formula_units_Z            1
_cell_measurement_temperature    90(2)
_cell_measurement_reflns_used    7285
_cell_measurement_theta_min      2.305
_cell_measurement_theta_max      30.86

_exptl_crystal_description       tablet
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.03
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.161
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1306
_exptl_absorpt_coefficient_mu    3.172
_exptl_absorpt_correction_type   none

_exptl_special_details           
;
Low temperature Bruker KRIOFLEX device.
;

_diffrn_ambient_temperature      90(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'SMART-APEX CCD diffractometer'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_standards_decay_%        0.00
_diffrn_reflns_number            38631
_diffrn_reflns_av_R_equivalents  0.0356
_diffrn_reflns_av_sigmaI/netI    0.0301
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         1.18
_diffrn_reflns_theta_max         31.00
_reflns_number_total             4493
_reflns_number_gt                4459
_reflns_threshold_expression     >2\s(I)

_computing_data_collection       'SMART (Bruker, 1999)'
_computing_cell_refinement       'SAINT (Bruker, 1999)'
_computing_data_reduction        'SAINT (Bruker, 1999)'
_computing_structure_solution    'SIR-92 (Altomare et al., 1994)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    
'ORTEP-III (Burnett and Johnson, 1996), Mercury 1.4, CCDC'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
H atoms were refined with some restraints (SADI and SIMU routines of
SHELX-97)
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[\s^2^(Fo^2^)+(0.0351P)^2^+6.6647P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_number_reflns         4493
_refine_ls_number_parameters     223
_refine_ls_number_restraints     177
_refine_ls_R_factor_all          0.0404
_refine_ls_R_factor_gt           0.0401
_refine_ls_wR_factor_ref         0.1069
_refine_ls_wR_factor_gt          0.1067
_refine_ls_goodness_of_fit_ref   1.356
_refine_ls_restrained_S_all      1.329
_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 1.0000 1.0000 0.85752(2) 0.01406(9) Uani 1 3 d S . .
I2 I 0.77824(2) 0.82787(2) 0.708932(12) 0.01631(8) Uani 1 1 d . . .
C7 C 0.6561(4) 0.7642(4) 0.6068(2) 0.0193(6) Uani 1 1 d . . .
F1 F 0.5535(3) 0.7808(3) 0.61892(17) 0.0326(6) Uani 1 1 d . . .
F2 F 0.7251(3) 0.8398(2) 0.54752(14) 0.0317(6) Uani 1 1 d . . .
C8 C 0.6057(3) 0.6209(3) 0.58643(19) 0.0144(6) Uani 1 1 d . . .
F3 F 0.7070(2) 0.6003(2) 0.58257(14) 0.0243(5) Uani 1 1 d . . .
F4 F 0.5274(2) 0.5480(2) 0.64421(13) 0.0241(5) Uani 1 1 d . . .
C9 C 0.5281(3) 0.5736(3) 0.50893(19) 0.0140(5) Uani 1 1 d . . .
F5 F 0.6079(2) 0.6437(2) 0.45077(12) 0.0193(4) Uani 1 1 d . . .
F6 F 0.4290(2) 0.5979(2) 0.51197(13) 0.0195(4) Uani 1 1 d . . .
K1 K 0.3333 0.6667 0.05713(7) 0.01136(19) Uani 1 3 d S . .
N1 N 0.3333 0.6667 -0.1113(3) 0.0144(9) Uani 1 3 d S . .
C1 C 0.2785(3) 0.5315(3) -0.1381(2) 0.0159(6) Uani 1 1 d DU . .
H1A H 0.341(4) 0.506(5) -0.131(2) 0.021(10) Uiso 1 1 d DU . .
H1B H 0.258(4) 0.525(5) -0.1898(13) 0.020(10) Uiso 1 1 d DU . .
C2 C 0.1563(3) 0.4353(3) -0.0955(2) 0.0158(6) Uani 1 1 d DU . .
H2A H 0.085(3) 0.447(4) -0.100(3) 0.024(11) Uiso 1 1 d DU . .
H2B H 0.137(4) 0.356(3) -0.116(3) 0.017(10) Uiso 1 1 d DU . .
O1 O 0.1850(2) 0.4381(2) -0.01572(14) 0.0133(4) Uani 1 1 d . . .
C3 C 0.0782(3) 0.3387(3) 0.0263(2) 0.0161(6) Uani 1 1 d DU . .
H3A H 0.068(4) 0.259(3) 0.012(2) 0.007(8) Uiso 1 1 d DU . .
H3B H 0.003(3) 0.340(4) 0.013(3) 0.013(9) Uiso 1 1 d DU . .
C4 C 0.1060(3) 0.3627(3) 0.1112(2) 0.0164(6) Uani 1 1 d DU . .
H4A H 0.182(2) 0.361(4) 0.122(2) 0.010(9) Uiso 1 1 d DU . .
H4B H 0.037(3) 0.292(3) 0.135(3) 0.021(10) Uiso 1 1 d DU . .
O2 O 0.1065(2) 0.4795(2) 0.13095(14) 0.0140(4) Uani 1 1 d . . .
C5 C 0.0983(3) 0.4963(3) 0.21192(19) 0.0150(6) Uani 1 1 d DU . .
H5A H 0.031(3) 0.417(2) 0.229(3) 0.017(10) Uiso 1 1 d DU . .
H5B H 0.071(4) 0.558(3) 0.217(3) 0.014(9) Uiso 1 1 d DU . .
C6 C 0.2263(3) 0.5410(3) 0.25438(19) 0.0143(5) Uani 1 1 d DU . .
H6A H 0.209(5) 0.541(5) 0.3062(13) 0.021(10) Uiso 1 1 d DU . .
H6B H 0.245(5) 0.475(4) 0.244(2) 0.019(10) Uiso 1 1 d DU . .
N2 N 0.3333 0.6667 0.2269(3) 0.0117(8) Uani 1 3 d S . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
I1 0.01410(11) 0.01410(11) 0.01397(16) 0.000 0.000 0.00705(6)
I2 0.01520(11) 0.01640(11) 0.01564(12) -0.00095(7) -0.00159(7) 0.00664(8)
C7 0.0200(16) 0.0168(15) 0.0234(16) -0.0017(12) -0.0059(13) 0.0110(13)
F1 0.0344(14) 0.0348(14) 0.0433(15) -0.0176(12) -0.0197(12) 0.0283(12)
F2 0.0435(15) 0.0178(11) 0.0209(11) 0.0039(9) -0.0057(10) 0.0055(11)
C8 0.0145(14) 0.0151(14) 0.0135(13) 0.0006(11) -0.0015(11) 0.0072(12)
F3 0.0231(11) 0.0294(12) 0.0283(12) -0.0093(9) -0.0115(9) 0.0191(10)
F4 0.0262(11) 0.0218(11) 0.0142(9) 0.0039(8) 0.0009(8) 0.0044(9)
C9 0.0119(13) 0.0163(14) 0.0146(13) 0.0016(11) -0.0004(10) 0.0077(12)
F5 0.0202(10) 0.0155(9) 0.0166(9) 0.0032(7) 0.0033(8) 0.0047(8)
F6 0.0169(10) 0.0201(10) 0.0260(11) -0.0030(8) -0.0042(8) 0.0126(8)
K1 0.0102(3) 0.0102(3) 0.0136(5) 0.000 0.000 0.00511(14)
N1 0.0126(13) 0.0126(13) 0.018(2) 0.000 0.000 0.0063(6)
C1 0.0179(15) 0.0149(14) 0.0151(14) -0.0019(11) 0.0010(11) 0.0083(12)
C2 0.0153(14) 0.0125(13) 0.0165(14) -0.0021(11) -0.0024(11) 0.0046(11)
O1 0.0100(10) 0.0117(10) 0.0152(10) -0.0012(8) -0.0003(8) 0.0033(8)
C3 0.0132(13) 0.0110(13) 0.0196(15) -0.0009(11) 0.0026(11) 0.0025(11)
C4 0.0155(14) 0.0112(13) 0.0206(15) 0.0005(11) 0.0024(12) 0.0052(12)
O2 0.0135(10) 0.0123(10) 0.0157(11) 0.0000(8) 0.0002(8) 0.0061(9)
C5 0.0124(13) 0.0166(14) 0.0146(14) 0.0015(11) 0.0017(11) 0.0061(12)
C6 0.0137(13) 0.0132(13) 0.0144(13) 0.0012(10) 0.0017(10) 0.0056(11)
N2 0.0107(12) 0.0107(12) 0.014(2) 0.000 0.000 0.0054(6)

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I2 C7 2.169(4) . ?
C7 F2 1.340(5) . ?
C7 F1 1.342(4) . ?
C7 C8 1.535(5) . ?
C8 F3 1.343(4) . ?
C8 F4 1.345(4) . ?
C8 C9 1.564(5) . ?
C9 F6 1.344(4) . ?
C9 F5 1.347(4) . ?
C9 C9 1.558(7) 4_666 ?
K1 O1 2.696(2) 3_565 ?
K1 O1 2.696(2) . ?
K1 O1 2.696(2) 2_665 ?
K1 O2 2.798(2) 3_565 ?
K1 O2 2.798(2) . ?
K1 O2 2.798(2) 2_665 ?
K1 N1 2.917(5) . ?
K1 N2 2.941(5) . ?
N1 C1 1.472(4) 3_565 ?
N1 C1 1.472(4) 2_665 ?
N1 C1 1.472(4) . ?
C1 C2 1.514(5) . ?
C1 H1A 0.930(19) . ?
C1 H1B 0.921(19) . ?
C2 O1 1.419(4) . ?
C2 H2A 0.925(19) . ?
C2 H2B 0.919(19) . ?
O1 C3 1.425(4) . ?
C3 C4 1.502(5) . ?
C3 H3A 0.924(19) . ?
C3 H3B 0.926(19) . ?
C4 O2 1.425(4) . ?
C4 H4A 0.928(19) . ?
C4 H4B 0.923(19) . ?
O2 C5 1.426(4) . ?
C5 C6 1.524(5) . ?
C5 H5A 0.927(19) . ?
C5 H5B 0.933(19) . ?
C6 N2 1.472(4) . ?
C6 H6A 0.921(19) . ?
C6 H6B 0.927(19) . ?
N2 C6 1.472(4) 3_565 ?
N2 C6 1.472(4) 2_665 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
F2 C7 F1 108.5(3) . . ?
F2 C7 C8 109.6(3) . . ?
F1 C7 C8 108.6(3) . . ?
F2 C7 I2 108.3(2) . . ?
F1 C7 I2 108.5(2) . . ?
C8 C7 I2 113.3(2) . . ?
F3 C8 F4 108.3(3) . . ?
F3 C8 C7 108.9(3) . . ?
F4 C8 C7 107.6(3) . . ?
F3 C8 C9 108.2(3) . . ?
F4 C8 C9 108.3(3) . . ?
C7 C8 C9 115.3(3) . . ?
F6 C9 F5 108.5(3) . . ?
F6 C9 C9 108.5(3) . 4_666 ?
F5 C9 C9 108.5(3) . 4_666 ?
F6 C9 C8 108.1(3) . . ?
F5 C9 C8 108.4(3) . . ?
C9 C9 C8 114.7(3) 4_666 . ?
O1 K1 O1 99.87(7) 3_565 . ?
O1 K1 O1 99.87(7) 3_565 2_665 ?
O1 K1 O1 99.87(7) . 2_665 ?
O1 K1 O2 62.02(7) 3_565 3_565 ?
O1 K1 O2 153.18(7) . 3_565 ?
O1 K1 O2 102.61(7) 2_665 3_565 ?
O1 K1 O2 102.61(7) 3_565 . ?
O1 K1 O2 62.02(7) . . ?
O1 K1 O2 153.18(7) 2_665 . ?
O2 K1 O2 100.77(7) 3_565 . ?
O1 K1 O2 153.18(7) 3_565 2_665 ?
O1 K1 O2 102.61(7) . 2_665 ?
O1 K1 O2 62.02(7) 2_665 2_665 ?
O2 K1 O2 100.77(7) 3_565 2_665 ?
O2 K1 O2 100.77(7) . 2_665 ?
O1 K1 N1 62.09(6) 3_565 . ?
O1 K1 N1 62.09(6) . . ?
O1 K1 N1 62.09(6) 2_665 . ?
O2 K1 N1 117.19(5) 3_565 . ?
O2 K1 N1 117.19(5) . . ?
O2 K1 N1 117.19(5) 2_665 . ?
O1 K1 N2 117.91(6) 3_565 . ?
O1 K1 N2 117.91(6) . . ?
O1 K1 N2 117.91(6) 2_665 . ?
O2 K1 N2 62.81(5) 3_565 . ?
O2 K1 N2 62.81(5) . . ?
O2 K1 N2 62.81(5) 2_665 . ?
N1 K1 N2 180.0 . . ?
C1 N1 C1 110.5(2) 3_565 2_665 ?
C1 N1 C1 110.5(2) 3_565 . ?
C1 N1 C1 110.5(2) 2_665 . ?
N1 C1 C2 113.7(3) . . ?
N1 C1 H1A 109(3) . . ?
C2 C1 H1A 108(3) . . ?
N1 C1 H1B 111(3) . . ?
C2 C1 H1B 107(3) . . ?
H1A C1 H1B 109(3) . . ?
O1 C2 C1 109.2(3) . . ?
O1 C2 H2A 108(3) . . ?
C1 C2 H2A 116(3) . . ?
O1 C2 H2B 109(3) . . ?
C1 C2 H2B 104(3) . . ?
H2A C2 H2B 110(3) . . ?
C2 O1 C3 112.0(3) . . ?
O1 C3 C4 108.8(3) . . ?
O1 C3 H3A 109(3) . . ?
C4 C3 H3A 111(3) . . ?
O1 C3 H3B 109(3) . . ?
C4 C3 H3B 111(3) . . ?
H3A C3 H3B 109(2) . . ?
O2 C4 C3 108.3(3) . . ?
O2 C4 H4A 116(3) . . ?
C3 C4 H4A 108(3) . . ?
O2 C4 H4B 110(3) . . ?
C3 C4 H4B 105(3) . . ?
H4A C4 H4B 109(3) . . ?
C4 O2 C5 113.9(3) . . ?
O2 C5 C6 113.4(3) . . ?
O2 C5 H5A 104(3) . . ?
C6 C5 H5A 114(3) . . ?
O2 C5 H5B 106(3) . . ?
C6 C5 H5B 111(3) . . ?
H5A C5 H5B 108(3) . . ?
N2 C6 C5 113.6(3) . . ?
N2 C6 H6A 113(3) . . ?
C5 C6 H6A 107(3) . . ?
N2 C6 H6B 110(3) . . ?
C5 C6 H6B 103(3) . . ?
H6A C6 H6B 109(3) . . ?
C6 N2 C6 110.1(2) 3_565 . ?
C6 N2 C6 110.1(2) 3_565 2_665 ?
C6 N2 C6 110.1(2) . 2_665 ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
F2 C7 C8 F3 68.4(4) . . . . ?
F1 C7 C8 F3 -173.3(3) . . . . ?
I2 C7 C8 F3 -52.6(3) . . . . ?
F2 C7 C8 F4 -174.4(3) . . . . ?
F1 C7 C8 F4 -56.1(4) . . . . ?
I2 C7 C8 F4 64.5(3) . . . . ?
F2 C7 C8 C9 -53.4(4) . . . . ?
F1 C7 C8 C9 64.9(4) . . . . ?
I2 C7 C8 C9 -174.4(2) . . . . ?
F3 C8 C9 F6 -178.2(3) . . . . ?
F4 C8 C9 F6 64.7(3) . . . . ?
C7 C8 C9 F6 -56.0(4) . . . . ?
F3 C8 C9 F5 -60.8(3) . . . . ?
F4 C8 C9 F5 -178.0(3) . . . . ?
C7 C8 C9 F5 61.4(4) . . . . ?
F3 C8 C9 C9 60.6(4) . . . 4_666 ?
F4 C8 C9 C9 -56.5(4) . . . 4_666 ?
C7 C8 C9 C9 -177.2(3) . . . 4_666 ?
C1 N1 C1 C2 -73.6(5) 3_565 . . . ?
C1 N1 C1 C2 163.6(3) 2_665 . . . ?
N1 C1 C2 O1 -59.8(4) . . . . ?
C1 C2 O1 C3 -172.9(3) . . . . ?
C2 O1 C3 C4 -169.7(3) . . . . ?
O1 C3 C4 O2 66.9(3) . . . . ?
C3 C4 O2 C5 164.7(3) . . . . ?
C4 O2 C5 C6 77.1(3) . . . . ?
O2 C5 C6 N2 60.0(4) . . . . ?
C5 C6 N2 C6 74.2(5) . . . 3_565 ?
C5 C6 N2 C6 -164.3(3) . . . 2_665 ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        31.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         2.638
_refine_diff_density_min         -0.799
_refine_diff_density_rms         0.171

_chemical_name_common            
;
2(4,7,13,16,21,24-hexaoxa-1,10-
diazabicyclo(8.8.8)hexacosane.potassium iodide)
3(1,1,2,2,3,3,4,4,5,5,6,6-dodecafluoro-1,6-diiodohexane)
;