# Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2003 data_global _publ_contact_author_email PAUL.CLARKE@NOTTINGHAM.AC.UK _publ_contact_author_name 'Dr Paul Clarke' _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _journal_year ? _journal_volume ? _journal_page_first ? loop_ _publ_author_name P.Clarke M.Ebden M.Grist C.Wilson data_ibutac _database_code_CSD 207876 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C15 H25 I O5' _chemical_formula_weight 412.25 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 6.5249(5) _cell_length_b 11.3828(9) _cell_length_c 13.3018(10) _cell_angle_alpha 65.415(1) _cell_angle_beta 77.402(1) _cell_angle_gamma 81.897(1) _cell_volume 875.35(12) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 4648 _cell_measurement_theta_min 3.1 _cell_measurement_theta_max 27.45 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.564 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 416 _exptl_absorpt_coefficient_mu 1.846 _exptl_absorpt_correction_type integration _exptl_absorpt_correction_T_min 0.530 _exptl_absorpt_correction_T_max 0.831 _exptl_absorpt_process_details 'Bruker Shelxtl v6.12' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'normal-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART1000 CCD area detector' _diffrn_measurement_method omega _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% none _diffrn_reflns_number 7666 _diffrn_reflns_av_R_equivalents 0.028 _diffrn_reflns_av_sigmaI/netI 0.0170 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.71 _diffrn_reflns_theta_max 27.48 _reflns_number_total 3876 _reflns_number_gt 3298 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART version 5.624 (Bruker, 2001)' _computing_cell_refinement 'Bruker SAINT version 6.36a (Bruker, 2002)' _computing_data_reduction 'Bruker SAINT; Bruker SHELXTL (Bruker, 2001)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material 'SHELXL-97; PLATON (Spek, 2001)' _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 _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0287P)^2^+1.4585P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens 'geometrically placed, OH from delta-F' _refine_ls_hydrogen_treatment 'riding model, OH rigid rotors' _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3876 _refine_ls_number_parameters 192 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0418 _refine_ls_R_factor_gt 0.0347 _refine_ls_wR_factor_ref 0.0814 _refine_ls_wR_factor_gt 0.0771 _refine_ls_goodness_of_fit_ref 1.059 _refine_ls_restrained_S_all 1.059 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group I1 I 0.85878(4) -0.15680(2) 0.96012(2) 0.05959(11) Uani 1 1 d . . . O1 O 0.7066(3) 0.37554(17) 0.57290(17) 0.0295(4) Uani 1 1 d . . . H1 H 0.5945 0.3521 0.5675 0.035 Uiso 1 1 calc R . . O2 O 0.8019(3) 0.16423(17) 0.63849(16) 0.0274(4) Uani 1 1 d . . . O3 O 1.3458(3) 0.35862(19) 0.5226(2) 0.0377(5) Uani 1 1 d . . . H3 H 1.3116 0.4378 0.4917 0.045 Uiso 1 1 calc R . . O4 O 0.7211(4) 0.3811(3) 0.8637(2) 0.0558(7) Uani 1 1 d . . . O5 O 0.4516(3) 0.4433(2) 0.7669(2) 0.0405(5) Uani 1 1 d . . . C1 C 0.7908(4) 0.2778(2) 0.6615(2) 0.0263(5) Uani 1 1 d . . . C2 C 1.0100(4) 0.3196(2) 0.6514(2) 0.0284(6) Uani 1 1 d . . . H2A H 1.0048 0.4141 0.6308 0.034 Uiso 1 1 calc R . . H2B H 1.0587 0.2749 0.7243 0.034 Uiso 1 1 calc R . . C3 C 1.1613(4) 0.2855(3) 0.5618(2) 0.0293(6) Uani 1 1 d . . . H3A H 1.0887 0.3070 0.4969 0.035 Uiso 1 1 calc R . . C4 C 1.2394(4) 0.1418(3) 0.6023(3) 0.0342(6) Uani 1 1 d . . . H4A H 1.2310 0.1104 0.5443 0.041 Uiso 1 1 calc R . . H4B H 1.3895 0.1356 0.6083 0.041 Uiso 1 1 calc R . . C5 C 1.1205(4) 0.0516(3) 0.7146(3) 0.0324(6) Uani 1 1 d . . . H5A H 1.1312 0.0814 0.7733 0.039 Uiso 1 1 calc R . . H5B H 1.1896 -0.0364 0.7345 0.039 Uiso 1 1 calc R . . C6 C 0.8864(4) 0.0437(2) 0.7156(2) 0.0306(6) Uani 1 1 d . . . C7 C 0.7458(5) 0.0167(3) 0.8308(3) 0.0385(7) Uani 1 1 d . . . H7A H 0.6026 0.0009 0.8252 0.046 Uiso 1 1 calc R . . C8 C 0.7220(5) 0.1289(3) 0.8665(3) 0.0414(7) Uani 1 1 d . . . H8A H 0.8593 0.1435 0.8783 0.050 Uiso 1 1 calc R . . H8B H 0.6212 0.1087 0.9381 0.050 Uiso 1 1 calc R . . C9 C 0.6419(5) 0.2510(3) 0.7748(2) 0.0328(6) Uani 1 1 d . . . H9A H 0.5011 0.2342 0.7669 0.039 Uiso 1 1 calc R . . C10 C 0.6133(5) 0.3656(3) 0.8083(3) 0.0383(7) Uani 1 1 d . . . C11 C 0.3779(5) 0.5607(3) 0.7900(3) 0.0450(8) Uani 1 1 d . . . C12 C 0.2128(7) 0.6216(4) 0.7153(5) 0.0771(14) Uani 1 1 d . . . H12A H 0.0997 0.5624 0.7392 0.116 Uiso 1 1 calc R . . H12B H 0.2776 0.6386 0.6371 0.116 Uiso 1 1 calc R . . H12C H 0.1548 0.7032 0.7213 0.116 Uiso 1 1 calc R . . C13 C 0.2830(7) 0.5185(4) 0.9126(4) 0.0698(13) Uani 1 1 d . . . H13A H 0.3940 0.4798 0.9578 0.105 Uiso 1 1 calc R . . H13B H 0.1789 0.4545 0.9328 0.105 Uiso 1 1 calc R . . H13C H 0.2144 0.5936 0.9270 0.105 Uiso 1 1 calc R . . C14 C 0.5541(6) 0.6502(3) 0.7545(4) 0.0587(10) Uani 1 1 d . . . H14A H 0.6590 0.6097 0.8035 0.088 Uiso 1 1 calc R . . H14B H 0.4975 0.7320 0.7605 0.088 Uiso 1 1 calc R . . H14C H 0.6203 0.6672 0.6766 0.088 Uiso 1 1 calc R . . C15 C 0.8582(5) -0.0534(3) 0.6692(3) 0.0417(7) Uani 1 1 d . . . H15A H 0.7083 -0.0568 0.6706 0.063 Uiso 1 1 calc R . . H15B H 0.9137 -0.1392 0.7154 0.063 Uiso 1 1 calc R . . H15C H 0.9343 -0.0269 0.5917 0.063 Uiso 1 1 calc R . . 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 0.06691(18) 0.02853(12) 0.05216(16) 0.00510(9) -0.00043(11) 0.01116(10) O1 0.0205(9) 0.0216(9) 0.0408(11) -0.0036(8) -0.0126(8) -0.0011(7) O2 0.0237(9) 0.0197(8) 0.0378(10) -0.0092(8) -0.0087(8) 0.0002(7) O3 0.0196(9) 0.0247(9) 0.0579(14) -0.0020(9) -0.0136(9) -0.0029(7) O4 0.0616(16) 0.0529(15) 0.0666(17) -0.0364(14) -0.0257(14) 0.0172(12) O5 0.0352(11) 0.0279(10) 0.0572(14) -0.0201(10) -0.0065(10) 0.0091(9) C1 0.0219(12) 0.0176(11) 0.0363(14) -0.0069(10) -0.0086(10) 0.0016(9) C2 0.0247(13) 0.0205(12) 0.0405(15) -0.0097(11) -0.0133(11) 0.0013(10) C3 0.0194(12) 0.0242(12) 0.0405(15) -0.0066(11) -0.0094(11) -0.0030(10) C4 0.0221(13) 0.0260(13) 0.0510(18) -0.0131(13) -0.0048(12) -0.0001(10) C5 0.0258(13) 0.0212(12) 0.0453(17) -0.0091(12) -0.0089(12) 0.0046(10) C6 0.0262(13) 0.0178(12) 0.0412(15) -0.0065(11) -0.0053(11) 0.0013(10) C7 0.0353(15) 0.0208(13) 0.0430(17) -0.0010(12) -0.0018(13) 0.0041(11) C8 0.0454(18) 0.0289(14) 0.0363(16) -0.0060(12) -0.0006(13) 0.0073(13) C9 0.0299(14) 0.0233(13) 0.0386(15) -0.0088(11) -0.0035(12) 0.0034(11) C10 0.0367(16) 0.0286(14) 0.0433(17) -0.0134(13) -0.0008(13) 0.0050(12) C11 0.0428(18) 0.0260(14) 0.062(2) -0.0210(15) 0.0010(15) 0.0059(13) C12 0.064(3) 0.051(2) 0.125(4) -0.047(3) -0.033(3) 0.033(2) C13 0.079(3) 0.0397(19) 0.073(3) -0.0264(19) 0.027(2) -0.0008(19) C14 0.063(2) 0.0342(17) 0.070(3) -0.0221(18) 0.011(2) -0.0086(16) C15 0.0357(16) 0.0265(14) 0.063(2) -0.0190(14) -0.0074(15) -0.0023(12) _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 2.172(3) . ? O1 C1 1.395(3) . ? O2 C1 1.437(3) . ? O2 C6 1.449(3) . ? O3 C3 1.436(3) . ? O4 C10 1.199(4) . ? O5 C10 1.335(4) . ? O5 C11 1.486(3) . ? C1 C2 1.531(4) . ? C1 C9 1.540(4) . ? C2 C3 1.520(4) . ? C3 C4 1.542(4) . ? C4 C5 1.527(4) . ? C5 C6 1.540(4) . ? C6 C15 1.520(4) . ? C6 C7 1.536(4) . ? C7 C8 1.515(4) . ? C8 C9 1.534(4) . ? C9 C10 1.521(4) . ? C11 C13 1.505(5) . ? C11 C14 1.509(5) . ? C11 C12 1.520(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 C1 O2 C6 118.3(2) . . ? C10 O5 C11 122.1(3) . . ? O1 C1 O2 104.3(2) . . ? O1 C1 C2 105.1(2) . . ? O2 C1 C2 111.7(2) . . ? O1 C1 C9 111.7(2) . . ? O2 C1 C9 107.0(2) . . ? C2 C1 C9 116.5(2) . . ? C3 C2 C1 109.1(2) . . ? O3 C3 C2 111.0(2) . . ? O3 C3 C4 106.3(2) . . ? C2 C3 C4 113.9(2) . . ? C5 C4 C3 115.7(2) . . ? C4 C5 C6 114.3(2) . . ? O2 C6 C15 103.1(2) . . ? O2 C6 C7 106.0(2) . . ? C15 C6 C7 111.4(2) . . ? O2 C6 C5 111.1(2) . . ? C15 C6 C5 110.9(2) . . ? C7 C6 C5 113.8(3) . . ? C8 C7 C6 113.5(2) . . ? C8 C7 I1 109.6(2) . . ? C6 C7 I1 111.31(18) . . ? C7 C8 C9 109.2(3) . . ? C10 C9 C8 110.8(3) . . ? C10 C9 C1 112.3(2) . . ? C8 C9 C1 110.0(2) . . ? O4 C10 O5 126.6(3) . . ? O4 C10 C9 124.1(3) . . ? O5 C10 C9 109.3(3) . . ? O5 C11 C13 108.4(3) . . ? O5 C11 C14 111.1(3) . . ? C13 C11 C14 112.7(4) . . ? O5 C11 C12 101.7(3) . . ? C13 C11 C12 111.9(4) . . ? C14 C11 C12 110.5(3) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 O2 C1 O1 179.3(2) . . . . ? C6 O2 C1 C2 66.3(3) . . . . ? C6 O2 C1 C9 -62.2(3) . . . . ? O1 C1 C2 C3 -80.4(2) . . . . ? O2 C1 C2 C3 32.1(3) . . . . ? C9 C1 C2 C3 155.4(2) . . . . ? C1 C2 C3 O3 160.7(2) . . . . ? C1 C2 C3 C4 -79.3(3) . . . . ? O3 C3 C4 C5 135.2(3) . . . . ? C2 C3 C4 C5 12.7(4) . . . . ? C3 C4 C5 C6 62.2(3) . . . . ? C1 O2 C6 C15 176.0(2) . . . . ? C1 O2 C6 C7 58.9(3) . . . . ? C1 O2 C6 C5 -65.1(3) . . . . ? C4 C5 C6 O2 -30.2(3) . . . . ? C4 C5 C6 C15 83.8(3) . . . . ? C4 C5 C6 C7 -149.8(2) . . . . ? O2 C6 C7 C8 -53.0(3) . . . . ? C15 C6 C7 C8 -164.3(3) . . . . ? C5 C6 C7 C8 69.4(3) . . . . ? O2 C6 C7 I1 -177.10(17) . . . . ? C15 C6 C7 I1 71.5(3) . . . . ? C5 C6 C7 I1 -54.7(3) . . . . ? C6 C7 C8 C9 55.0(3) . . . . ? I1 C7 C8 C9 -179.9(2) . . . . ? C7 C8 C9 C10 179.3(3) . . . . ? C7 C8 C9 C1 -55.9(3) . . . . ? O1 C1 C9 C10 -65.5(3) . . . . ? O2 C1 C9 C10 -179.0(2) . . . . ? C2 C1 C9 C10 55.3(3) . . . . ? O1 C1 C9 C8 170.6(2) . . . . ? O2 C1 C9 C8 57.0(3) . . . . ? C2 C1 C9 C8 -68.6(3) . . . . ? C11 O5 C10 O4 -2.7(5) . . . . ? C11 O5 C10 C9 177.0(2) . . . . ? C8 C9 C10 O4 32.8(4) . . . . ? C1 C9 C10 O4 -90.7(4) . . . . ? C8 C9 C10 O5 -146.9(3) . . . . ? C1 C9 C10 O5 89.6(3) . . . . ? C10 O5 C11 C13 -68.1(4) . . . . ? C10 O5 C11 C14 56.3(4) . . . . ? C10 O5 C11 C12 173.8(3) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1 H1 O3 0.84 1.83 2.636(3) 160.5 1_455 O3 H3 O1 0.84 1.93 2.754(3) 167.1 2_766 _diffrn_measured_fraction_theta_max 0.963 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.963 _refine_diff_density_max 1.477 _refine_diff_density_min -1.170 _refine_diff_density_rms 0.076