data_shelxl _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H27 I O4' _chemical_formula_weight 434.30 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 orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21 ' _symmetry_Int_Tables_number 19 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x+1/2, -y, z+1/2' _cell_length_a 6.094(6) _cell_length_b 15.229(14) _cell_length_c 20.355(18) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1889(3) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.527 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 880 _exptl_absorpt_coefficient_mu 1.712 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7569 _diffrn_reflns_av_R_equivalents 0.0178 _diffrn_reflns_av_sigmaI/netI 0.0580 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 2.67 _diffrn_reflns_theta_max 25.03 _reflns_number_total 3329 _reflns_number_gt 2901 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0000P)^2^+0.0000P] 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_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.027(14) _refine_ls_number_reflns 3329 _refine_ls_number_parameters 215 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0243 _refine_ls_R_factor_gt 0.0196 _refine_ls_wR_factor_ref 0.0299 _refine_ls_wR_factor_gt 0.0288 _refine_ls_goodness_of_fit_ref 0.744 _refine_ls_restrained_S_all 0.744 _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_symetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group I1 I -0.04008(3) 0.572897(12) 0.213940(10) 0.03173(5) Uani 1 1 d . . . O1 O 0.3432(3) 0.69439(11) 0.32749(9) 0.0204(5) Uani 1 1 d . . . O2 O 0.0185(3) 0.71244(10) 0.37904(8) 0.0258(4) Uani 1 1 d . . . O3 O 0.1506(3) 0.61465(11) 0.48216(9) 0.0200(4) Uani 1 1 d . . . O4 O 0.1355(3) 0.51835(13) 0.56479(11) 0.0375(6) Uani 1 1 d . . . C2 C 0.2608(4) 0.62545(17) 0.17904(14) 0.0208(7) Uani 1 1 d . . . H2 H 0.3634 0.5809 0.1628 0.028 Uiso 1 1 calc R . . C3 C 0.3707(4) 0.70188(14) 0.21283(15) 0.0193(6) Uani 1 1 d . . . H3 H 0.5311 0.6977 0.2141 0.026 Uiso 1 1 calc R . . C1 C 0.2771(5) 0.71222(17) 0.14387(15) 0.0233(7) Uani 1 1 d . . . C4 C 0.0762(5) 0.76866(16) 0.13204(14) 0.0338(8) Uani 1 1 d . . . H4A H 0.0027 0.7492 0.0929 0.051 Uiso 1 1 calc R . . H4B H 0.1201 0.8288 0.1268 0.051 Uiso 1 1 calc R . . H4C H -0.0216 0.7637 0.1688 0.051 Uiso 1 1 calc R . . C5 C 0.4397(5) 0.71360(17) 0.08816(13) 0.0309(8) Uani 1 1 d . . . H5A H 0.5580 0.6740 0.0977 0.046 Uiso 1 1 calc R . . H5B H 0.4966 0.7720 0.0830 0.046 Uiso 1 1 calc R . . H5C H 0.3681 0.6958 0.0483 0.046 Uiso 1 1 calc R . . C6 C 0.2733(4) 0.74688(16) 0.27139(14) 0.0223(7) Uani 1 1 d . . . H6 H 0.1128 0.7463 0.2682 0.030 Uiso 1 1 calc R . . C7 C 0.3534(5) 0.84050(17) 0.28134(19) 0.0371(8) Uani 1 1 d . . . H7A H 0.2991 0.8763 0.2454 0.049 Uiso 1 1 calc R . . H7B H 0.2894 0.8631 0.3216 0.049 Uiso 1 1 calc R . . C8 C 0.6002(5) 0.85127(18) 0.2852(2) 0.0529(10) Uani 1 1 d . . . H8A H 0.6585 0.8110 0.3170 0.079 Uiso 1 1 calc R . . H8B H 0.6348 0.9103 0.2981 0.079 Uiso 1 1 calc R . . H8C H 0.6637 0.8393 0.2430 0.079 Uiso 1 1 calc R . . C9 C 0.2018(5) 0.68424(16) 0.37778(14) 0.0185(7) Uani 1 1 d . . . C10 C 0.3145(4) 0.63373(17) 0.43112(13) 0.0176(7) Uani 1 1 d . . . C11 C 0.5008(4) 0.68215(14) 0.46665(13) 0.0217(7) Uani 1 1 d . . . H11A H 0.4451 0.7303 0.4930 0.029 Uiso 1 1 calc R . . H11B H 0.6088 0.7044 0.4359 0.029 Uiso 1 1 calc R . . C12 C 0.5971(4) 0.60874(16) 0.51005(14) 0.0265(7) Uani 1 1 d . . . H12A H 0.5814 0.6229 0.5563 0.035 Uiso 1 1 calc R . . H12B H 0.7513 0.5995 0.5004 0.035 Uiso 1 1 calc R . . C13 C 0.4603(5) 0.52701(14) 0.49190(12) 0.0182(6) Uani 1 1 d . . . C14 C 0.2355(5) 0.54822(18) 0.51949(15) 0.0234(7) Uani 1 1 d . . . C15 C 0.4106(4) 0.54150(15) 0.41737(13) 0.0169(7) Uani 1 1 d . . . C16 C 0.6144(4) 0.54000(17) 0.37395(14) 0.0284(8) Uani 1 1 d . . . H16A H 0.5746 0.5555 0.3298 0.043 Uiso 1 1 calc R . . H16B H 0.6771 0.4822 0.3743 0.043 Uiso 1 1 calc R . . H16C H 0.7197 0.5814 0.3904 0.043 Uiso 1 1 calc R . . C17 C 0.2424(5) 0.47685(16) 0.38965(16) 0.0285(8) Uani 1 1 d . . . H17A H 0.2031 0.4941 0.3458 0.043 Uiso 1 1 calc R . . H17B H 0.1138 0.4769 0.4169 0.043 Uiso 1 1 calc R . . H17C H 0.3046 0.4189 0.3888 0.043 Uiso 1 1 calc R . . C18 C 0.5526(5) 0.43988(16) 0.51397(13) 0.0306(7) Uani 1 1 d . . . H18A H 0.5674 0.4397 0.5609 0.046 Uiso 1 1 calc R . . H18B H 0.6938 0.4310 0.4942 0.046 Uiso 1 1 calc R . . H18C H 0.4553 0.3935 0.5008 0.046 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 0.02889(9) 0.03659(10) 0.02972(10) 0.00584(10) 0.00123(10) -0.00965(10) O1 0.0189(11) 0.0220(11) 0.0202(12) 0.0049(9) 0.0048(9) 0.0039(9) O2 0.0199(12) 0.0326(10) 0.0248(11) 0.0030(8) 0.0029(10) 0.0086(10) O3 0.0157(10) 0.0236(10) 0.0207(11) 0.0026(9) 0.0067(9) 0.0020(9) O4 0.0337(13) 0.0467(13) 0.0322(14) 0.0171(11) 0.0109(11) 0.0052(11) C2 0.0156(16) 0.0242(16) 0.0227(18) 0.0046(13) 0.0048(14) -0.0027(13) C3 0.0205(13) 0.0151(13) 0.0223(15) 0.0011(14) 0.0037(16) 0.0011(11) C1 0.0263(17) 0.0216(16) 0.0220(18) 0.0016(14) 0.0005(14) -0.0025(14) C4 0.0364(19) 0.0320(16) 0.0329(19) 0.0113(14) -0.0073(16) 0.0016(16) C5 0.0359(19) 0.0328(17) 0.0241(17) 0.0012(13) 0.0052(17) -0.0074(18) C6 0.0242(16) 0.0223(16) 0.0204(19) 0.0045(13) 0.0000(13) 0.0045(13) C7 0.068(2) 0.0189(16) 0.0240(19) -0.0015(17) 0.008(2) 0.0041(15) C8 0.075(3) 0.0323(19) 0.051(2) -0.008(2) 0.007(3) -0.0281(17) C9 0.0243(18) 0.0093(15) 0.0218(18) -0.0021(12) 0.0011(14) -0.0031(14) C10 0.0151(16) 0.0210(16) 0.0166(16) -0.0019(13) 0.0048(13) -0.0053(13) C11 0.0193(19) 0.0221(14) 0.0238(15) -0.0055(12) -0.0011(14) -0.0017(14) C12 0.0210(18) 0.0328(17) 0.0256(17) -0.0067(13) -0.0051(13) 0.0007(14) C13 0.0179(14) 0.0200(13) 0.0168(14) 0.0001(11) 0.0011(14) 0.0010(14) C14 0.0214(16) 0.0262(18) 0.0226(18) -0.0004(14) -0.0021(14) -0.0016(14) C15 0.0188(17) 0.0134(14) 0.0187(15) -0.0014(11) -0.0002(12) 0.0016(12) C16 0.0288(17) 0.0298(17) 0.0265(19) -0.0008(13) 0.0085(14) 0.0114(14) C17 0.0335(19) 0.0198(16) 0.032(2) 0.0009(15) -0.0079(16) 0.0008(15) C18 0.0310(15) 0.0351(16) 0.0257(16) 0.0030(13) 0.0026(15) 0.0067(17) _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 C2 2.123(3) . ? O1 C9 1.347(3) . ? O1 C6 1.458(3) . ? O2 C9 1.197(3) . ? O3 C14 1.367(3) . ? O3 C10 1.470(3) . ? O4 C14 1.195(3) . ? C2 C1 1.506(4) . ? C2 C3 1.509(4) . ? C3 C6 1.498(4) . ? C3 C1 1.523(4) . ? C1 C5 1.506(4) . ? C1 C4 1.515(4) . ? C6 C7 1.521(4) . ? C7 C8 1.515(4) . ? C9 C10 1.497(4) . ? C10 C11 1.535(3) . ? C10 C15 1.547(4) . ? C11 C12 1.541(3) . ? C12 C13 1.543(3) . ? C13 C18 1.510(3) . ? C13 C14 1.515(4) . ? C13 C15 1.563(4) . ? C15 C16 1.524(4) . ? C15 C17 1.529(4) . ? 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 C9 O1 C6 118.1(2) . . ? C14 O3 C10 106.4(2) . . ? C1 C2 C3 60.69(19) . . ? C1 C2 I1 123.16(19) . . ? C3 C2 I1 121.5(2) . . ? C6 C3 C2 122.7(2) . . ? C6 C3 C1 122.5(2) . . ? C2 C3 C1 59.57(18) . . ? C5 C1 C2 114.4(2) . . ? C5 C1 C4 113.8(2) . . ? C2 C1 C4 121.3(2) . . ? C5 C1 C3 116.7(2) . . ? C2 C1 C3 59.74(17) . . ? C4 C1 C3 120.5(2) . . ? O1 C6 C3 104.9(2) . . ? O1 C6 C7 108.4(2) . . ? C3 C6 C7 114.1(2) . . ? C8 C7 C6 115.3(3) . . ? O2 C9 O1 124.9(3) . . ? O2 C9 C10 126.6(3) . . ? O1 C9 C10 108.4(2) . . ? O3 C10 C9 107.6(2) . . ? O3 C10 C11 105.3(2) . . ? C9 C10 C11 115.7(2) . . ? O3 C10 C15 101.9(2) . . ? C9 C10 C15 120.6(2) . . ? C11 C10 C15 104.0(2) . . ? C10 C11 C12 101.7(2) . . ? C11 C12 C13 104.0(2) . . ? C18 C13 C14 114.5(2) . . ? C18 C13 C12 115.9(2) . . ? C14 C13 C12 103.2(2) . . ? C18 C13 C15 119.0(2) . . ? C14 C13 C15 98.9(2) . . ? C12 C13 C15 102.90(19) . . ? O4 C14 O3 121.2(3) . . ? O4 C14 C13 131.7(3) . . ? O3 C14 C13 107.1(2) . . ? C16 C15 C17 108.8(2) . . ? C16 C15 C10 115.3(2) . . ? C17 C15 C10 113.4(2) . . ? C16 C15 C13 113.8(2) . . ? C17 C15 C13 113.4(2) . . ? C10 C15 C13 91.48(19) . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.03 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.498 _refine_diff_density_min -0.463 _refine_diff_density_rms 0.051