# Supplementary Material (ESI) for New Journal of Chemistry # This journal is © The Royal Society of Chemistry and # The Centre National de la Recherche Scientifique, 2000 # CCDC Number: 440/194 data_re12 _audit_creation_method SHELXL-97 _chemical_name_systematic ; 1,7,10,16-Tetraoxa-4,13-diazacyclo-octadecane 1,8-diiodoperfluorooctane ; _chemical_formula_moiety '(C12 H26 N2 O4).(C8 F16 I2)' _chemical_formula_sum 'C20 H26 F16 I2 N2 O4' _chemical_formula_weight 916.23 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 I2/a loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y, -z' 'x+1/2, y+1/2, z+1/2' '-x+1, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y, z' '-x+1/2, -y+1/2, -z+1/2' 'x, -y+1/2, z+1/2' _cell_length_a 31.1690(13) _cell_length_b 5.4620(2) _cell_length_c 19.6270(8) _cell_angle_alpha 90.00 _cell_angle_beta 102.81 _cell_angle_gamma 90.00 _cell_volume 3258.2(2) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _exptl_crystal_description Hemisfere _exptl_crystal_colour colourless _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.20 _exptl_crystal_density_diffrn 1.868 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1768 _exptl_absorpt_coefficient_mu 2.050 _exptl_absorpt_correction_type 'multi-scan (SADABS, Sheldrick, 1996)' _exptl_absorpt_correction_T_min 1.000000 _exptl_absorpt_correction_T_max 0.589393 _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Siemens SMART CCD diffractometer' _diffrn_measurement_method '\w scans' _diffrn_reflns_number 14323 _diffrn_standards_decay_% 0.00 _diffrn_reflns_av_R_equivalents 0.0253 _diffrn_reflns_av_sigmaI/netI 0.0175 _diffrn_reflns_limit_h_min -39 _diffrn_reflns_limit_h_max 40 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 2.13 _diffrn_reflns_theta_max 28.27 _reflns_number_total 3687 _reflns_number_gt 2613 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Siemens, 1995)' _computing_cell_refinement 'SMART (Siemens, 1995)' _computing_data_reduction 'SAINT (Siemens, 1995)' _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)' _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. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme 'calc w=1/[\s^2^(Fo^2^)+(0.0664P)^2^+2.7203P] 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 mixed _refine_ls_extinction_method none _refine_ls_number_reflns 3687 _refine_ls_number_parameters 210 _refine_ls_number_restraints 46 _refine_ls_R_factor_all 0.0572 _refine_ls_R_factor_gt 0.0413 _refine_ls_wR_factor_ref 0.1242 _refine_ls_wR_factor_gt 0.1153 _refine_ls_goodness_of_fit_ref 1.060 _refine_ls_restrained_S_all 1.072 _refine_ls_shift/su_max 0.007 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group I I 0.373461(10) 0.09232(6) 0.303473(15) 0.08763(17) Uani 1 d . . . C7 C 0.3150(2) -0.0629(9) 0.2345(3) 0.0930(14) Uani 1 d . . . F1 F 0.27834(11) 0.0193(9) 0.25173(17) 0.1219(11) Uani 1 d . . . F2 F 0.31587(16) -0.3059(6) 0.23972(19) 0.1465(16) Uani 1 d . . . C8 C 0.31236(13) 0.0070(8) 0.1576(2) 0.0695(9) Uani 1 d . . . F3 F 0.31650(10) 0.2495(4) 0.15430(14) 0.0944(8) Uani 1 d . . . F4 F 0.34681(9) -0.0973(6) 0.13782(15) 0.1036(10) Uani 1 d . . . C9 C 0.26947(14) -0.0679(7) 0.1040(2) 0.0704(10) Uani 1 d . . . F5 F 0.25997(11) -0.3024(6) 0.11528(15) 0.1065(9) Uani 1 d . . . F6 F 0.23638(9) 0.0708(6) 0.11549(16) 0.1040(10) Uani 1 d . . . C10 C 0.27215(12) -0.0407(7) 0.0271(2) 0.0648(9) Uani 1 d . . . F7 F 0.29697(9) -0.2224(6) 0.01043(14) 0.1025(9) Uani 1 d . . . F8 F 0.29257(9) 0.1720(6) 0.01964(14) 0.0947(8) Uani 1 d . . . O1 O 0.42994(10) 0.2080(8) 0.53592(17) 0.0956(9) Uani 1 d . . . C1 C 0.39985(18) 0.3472(12) 0.4897(3) 0.1027(16) Uani 1 d . . . H1A H 0.3849 0.4589 0.5152 0.123 Uiso 1 calc R . . H1B H 0.3780 0.2419 0.4612 0.123 Uiso 1 calc R . . C2 C 0.4238(2) 0.4888(11) 0.4442(3) 0.1041(16) Uani 1 d . . . H2A H 0.4035 0.5994 0.4146 0.125 Uiso 1 calc R . . H2B H 0.4467 0.5866 0.4733 0.125 Uiso 1 calc R . . N N 0.44365(12) 0.3267(8) 0.4002(2) 0.0822(10) Uani 1 d . . . H1N H 0.462(2) 0.222(14) 0.444(3) 0.15(2) Uiso 1 d . . . C3 C 0.47041(19) 0.4605(12) 0.3616(3) 0.1062(17) Uani 1 d DU . . H3A H 0.4896 0.5710 0.3930 0.127 Uiso 1 calc R . . H3B H 0.4515 0.5585 0.3259 0.127 Uiso 1 calc R . . C4 C 0.4970(2) 0.2991(15) 0.3285(3) 0.129(2) Uani 1 d DU . . H4A H 0.5108 0.3901 0.2967 0.155 Uiso 0.745(10) calc PR A 1 H4B H 0.4791 0.1700 0.3027 0.155 Uiso 0.745(10) calc PR A 1 H4C H 0.4799 0.2789 0.2811 0.155 Uiso 0.255(10) calc PR A 2 H4D H 0.5222 0.3976 0.3246 0.155 Uiso 0.255(10) calc PR A 2 O2 O 0.53058(16) 0.1960(10) 0.3872(2) 0.0890(17) Uani 0.745(10) d PDU A 1 C5 C 0.5577(2) 0.0514(16) 0.3650(3) 0.123(2) Uani 1 d DU . . H5A H 0.5732 0.1453 0.3361 0.148 Uiso 0.745(10) calc PR A 1 H5B H 0.5408 -0.0739 0.3357 0.148 Uiso 0.745(10) calc PR A 1 H5C H 0.5662 0.2223 0.3693 0.148 Uiso 0.255(10) calc PR A 2 H5D H 0.5655 -0.0050 0.3225 0.148 Uiso 0.255(10) calc PR A 2 C6 C 0.58963(16) -0.0668(9) 0.4198(3) 0.1016(17) Uani 1 d DU . . H6A H 0.6084 -0.1710 0.3988 0.122 Uiso 1 calc R . . H6B H 0.6081 0.0572 0.4472 0.122 Uiso 1 calc R . . O2' O 0.51487(16) 0.0603(9) 0.3481(3) 0.071(4) Uani 0.255(10) d PRDU A 2 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 I 0.0979(3) 0.0768(2) 0.0733(2) 0.00246(13) -0.01277(16) 0.00886(14) C7 0.109(4) 0.075(3) 0.083(3) -0.002(2) -0.004(3) 0.011(3) F1 0.097(2) 0.183(3) 0.089(2) -0.014(2) 0.0266(17) -0.006(2) F2 0.224(4) 0.0734(19) 0.108(2) 0.0240(17) -0.037(2) -0.031(2) C8 0.073(2) 0.0568(19) 0.071(2) 0.0000(18) 0.0002(18) 0.0040(18) F3 0.1173(19) 0.0639(14) 0.0851(16) 0.0059(12) -0.0142(14) -0.0119(14) F4 0.0695(14) 0.147(3) 0.0870(17) -0.0177(16) 0.0028(13) 0.0330(15) C9 0.068(2) 0.063(2) 0.076(2) 0.0027(18) 0.0056(18) 0.0007(18) F5 0.128(2) 0.0826(17) 0.0924(18) 0.0162(15) -0.0104(16) -0.0372(17) F6 0.0748(15) 0.150(3) 0.0855(17) -0.0097(16) 0.0130(13) 0.0297(17) C10 0.0562(19) 0.059(2) 0.074(2) -0.0004(17) 0.0047(17) 0.0016(16) F7 0.0868(16) 0.123(2) 0.0873(17) -0.0154(16) -0.0031(13) 0.0459(17) F8 0.0860(16) 0.1056(19) 0.0823(16) 0.0138(14) -0.0032(13) -0.0362(15) O1 0.0764(18) 0.123(3) 0.084(2) -0.001(2) 0.0117(16) -0.002(2) C1 0.092(3) 0.121(4) 0.095(4) -0.013(3) 0.021(3) 0.023(3) C2 0.122(4) 0.089(3) 0.095(3) -0.007(3) 0.011(3) 0.017(3) N 0.079(2) 0.090(2) 0.070(2) 0.0138(19) -0.0001(17) 0.004(2) C3 0.097(3) 0.115(4) 0.100(4) 0.037(3) 0.006(3) 0.003(3) C4 0.144(5) 0.152(6) 0.105(4) 0.056(4) 0.059(4) 0.014(5) O2 0.101(3) 0.109(4) 0.056(2) -0.006(2) 0.016(2) -0.008(3) C5 0.107(4) 0.189(7) 0.084(3) 0.008(4) 0.042(3) -0.030(5) C6 0.086(3) 0.116(4) 0.118(4) -0.009(3) 0.054(3) -0.007(3) O2' 0.077(7) 0.077(8) 0.064(7) 0.000(5) 0.024(5) -0.017(5) _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 I C7 2.185(5) . NO C7 F2 1.331(5) . NO C7 F1 1.340(7) . NO C7 C8 1.541(7) . NO C8 F3 1.334(5) . NO C8 F4 1.346(5) . NO C8 C9 1.561(6) . NO C9 F6 1.338(5) . NO C9 F5 1.344(5) . NO C9 C10 1.537(6) . NO C10 F7 1.342(5) . NO C10 F8 1.348(5) . NO C10 C10 1.545(7) 2 NO O1 C1 1.380(6) . NO O1 C6 1.399(6) 5_656 NO C1 C2 1.501(9) . NO C1 H1A 0.9700 . NO C1 H1B 0.9700 . NO C2 N 1.465(7) . NO C2 H2A 0.9700 . NO C2 H2B 0.9700 . NO N C3 1.444(7) . NO N H1N 1.09(7) . NO C3 C4 1.457(9) . NO C3 H3A 0.9700 . NO C3 H3B 0.9700 . NO C4 O2' 1.437(9) . NO C4 O2 1.485(8) . NO C4 H4A 0.9700 . NO C4 H4B 0.9700 . NO C4 H4C 0.9700 . NO C4 H4D 0.9700 . NO O2 C5 1.299(8) . NO C5 O2' 1.302(8) . NO C5 C6 1.446(9) . NO C5 H5A 0.9700 . NO C5 H5B 0.9700 . NO C5 H5C 0.9700 . NO C5 H5D 0.9700 . NO C6 O1 1.399(6) 5_656 NO C6 H6A 0.9700 . NO C6 H6B 0.9700 . NO 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(5) . . NO F2 C7 C8 108.6(4) . . NO F1 C7 C8 107.5(4) . . NO F2 C7 I 109.9(4) . . NO F1 C7 I 110.7(3) . . NO C8 C7 I 111.6(4) . . NO F3 C8 F4 108.3(4) . . NO F3 C8 C7 108.0(3) . . NO F4 C8 C7 107.7(4) . . NO F3 C8 C9 107.8(3) . . NO F4 C8 C9 108.3(3) . . NO C7 C8 C9 116.6(4) . . NO F6 C9 F5 107.8(4) . . NO F6 C9 C10 108.8(3) . . NO F5 C9 C10 108.4(3) . . NO F6 C9 C8 108.4(3) . . NO F5 C9 C8 109.0(3) . . NO C10 C9 C8 114.3(3) . . NO F7 C10 F8 107.4(3) . . NO F7 C10 C9 109.1(3) . . NO F8 C10 C9 108.6(3) . . NO F7 C10 C10 107.9(3) . 2 NO F8 C10 C10 107.3(3) . 2 NO C9 C10 C10 116.2(4) . 2 NO C1 O1 C6 112.7(4) . 5_656 NO O1 C1 C2 108.7(4) . . NO O1 C1 H1A 110.0 . . NO C2 C1 H1A 110.0 . . NO O1 C1 H1B 110.0 . . NO C2 C1 H1B 110.0 . . NO H1A C1 H1B 108.3 . . NO N C2 C1 111.7(5) . . NO N C2 H2A 109.3 . . NO C1 C2 H2A 109.3 . . NO N C2 H2B 109.3 . . NO C1 C2 H2B 109.3 . . NO H2A C2 H2B 107.9 . . NO C3 N C2 111.8(5) . . NO C3 N H1N 114(3) . . NO C2 N H1N 94(4) . . NO N C3 C4 112.3(5) . . NO N C3 H3A 109.1 . . NO C4 C3 H3A 109.1 . . NO N C3 H3B 109.1 . . NO C4 C3 H3B 109.1 . . NO H3A C3 H3B 107.9 . . NO O2' C4 C3 130.9(5) . . NO O2' C4 O2 44.2(3) . . NO C3 C4 O2 104.9(5) . . NO O2' C4 H4A 115.8 . . NO C3 C4 H4A 110.8 . . NO O2 C4 H4A 110.8 . . NO O2' C4 H4B 67.9 . . NO C3 C4 H4B 110.8 . . NO O2 C4 H4B 110.8 . . NO H4A C4 H4B 108.8 . . NO O2' C4 H4C 104.5 . . NO C3 C4 H4C 104.5 . . NO O2 C4 H4C 147.4 . . NO H4A C4 H4C 70.7 . . NO H4B C4 H4C 44.4 . . NO O2' C4 H4D 104.5 . . NO C3 C4 H4D 104.5 . . NO O2 C4 H4D 80.0 . . NO H4A C4 H4D 35.0 . . NO H4B C4 H4D 138.2 . . NO H4C C4 H4D 105.7 . . NO C5 O2 C4 111.7(5) . . NO O2 C5 O2' 50.0(4) . . NO O2 C5 C6 114.5(5) . . NO O2' C5 C6 134.8(6) . . NO O2 C5 H5A 108.6 . . NO O2' C5 H5A 116.6 . . NO C6 C5 H5A 108.6 . . NO O2 C5 H5B 108.6 . . NO O2' C5 H5B 59.0 . . NO C6 C5 H5B 108.6 . . NO H5A C5 H5B 107.6 . . NO O2 C5 H5C 64.7 . . NO O2' C5 H5C 103.5 . . NO C6 C5 H5C 103.5 . . NO H5A C5 H5C 51.6 . . NO H5B C5 H5C 146.5 . . NO O2 C5 H5D 142.0 . . NO O2' C5 H5D 103.5 . . NO C6 C5 H5D 103.5 . . NO H5A C5 H5D 53.9 . . NO H5B C5 H5D 58.3 . . NO H5C C5 H5D 105.3 . . NO O1 C6 C5 112.6(4) 5_656 . NO O1 C6 H6A 109.1 5_656 . NO C5 C6 H6A 109.1 . . NO O1 C6 H6B 109.1 5_656 . NO C5 C6 H6B 109.1 . . NO H6A C6 H6B 107.8 . . NO C5 O2' C4 114.7(6) . . NO 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 -173.2(4) . . . . NO F1 C7 C8 F3 69.6(5) . . . . NO I C7 C8 F3 -52.0(4) . . . . NO F2 C7 C8 F4 -56.4(6) . . . . NO F1 C7 C8 F4 -173.6(4) . . . . NO I C7 C8 F4 64.8(4) . . . . NO F2 C7 C8 C9 65.4(6) . . . . NO F1 C7 C8 C9 -51.8(5) . . . . NO I C7 C8 C9 -173.4(3) . . . . NO F3 C8 C9 F6 -51.4(4) . . . . NO F4 C8 C9 F6 -168.4(3) . . . . NO C7 C8 C9 F6 70.1(5) . . . . NO F3 C8 C9 F5 -168.5(4) . . . . NO F4 C8 C9 F5 74.6(4) . . . . NO C7 C8 C9 F5 -47.0(5) . . . . NO F3 C8 C9 C10 70.1(4) . . . . NO F4 C8 C9 C10 -46.9(4) . . . . NO C7 C8 C9 C10 -168.4(4) . . . . NO F6 C9 C10 F7 -164.3(3) . . . . NO F5 C9 C10 F7 -47.3(4) . . . . NO C8 C9 C10 F7 74.5(4) . . . . NO F6 C9 C10 F8 78.9(4) . . . . NO F5 C9 C10 F8 -164.1(3) . . . . NO C8 C9 C10 F8 -42.3(4) . . . . NO F6 C9 C10 C10 -42.0(3) . . . 2 NO F5 C9 C10 C10 74.9(3) . . . 2 NO C8 C9 C10 C10 -163.3(2) . . . 2 NO C6 O1 C1 C2 -179.3(4) 5_656 . . . NO O1 C1 C2 N 64.6(6) . . . . NO C1 C2 N C3 -174.2(4) . . . . NO C2 N C3 C4 168.8(5) . . . . NO N C3 C4 O2 -70.0(7) . . . . NO C3 C4 O2 C5 -178.4(6) . . . . NO C4 O2 C5 C6 -176.5(5) . . . . NO O2 C5 C6 O1 58.7(8) . . . 5_656 NO N C3 C4 O2' -28.7(11) . . . . NO O2' C4 O2 C5 47.3(5) . . . . NO C4 O2 C5 O2' -47.5(5) . . . . NO O2' C5 C6 O1 1.5(13) . . . 5_656 NO O2 C5 O2' C4 51.2(5) . . . . NO C6 C5 O2' C4 137.2(9) . . . . NO C3 C4 O2' C5 -114.8(9) . . . . NO O2 C4 O2' C5 -48.6(5) . . . . NO _diffrn_measured_fraction_theta_max 0.414 _diffrn_reflns_theta_full 28.27 _diffrn_measured_fraction_theta_full 0.414 _refine_diff_density_max 1.464 _refine_diff_density_min -0.433 _refine_diff_density_rms 0.069