data_shelxl _audit_creation_method SHELXL-97 _publ_section_references ; CrystalClear, Rigaku Corp., (1999) Altomare, A., M. Burla, M. Camalli, G. Cascarano, C. Giacovazzo A. Guagliardi, A. Moliterni, G. Polidori & R. Spagna. (1999) J. Appl. Cryst. 32, 115-119. Sheldrick, G.M. SHELXL97. Program for crystal structure refinement. University of Gottingen, Germany, 1997. ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H29 I O4' _chemical_formula_weight 460.33 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 6.8584(3) _cell_length_b 13.6465(8) _cell_length_c 21.3782(14) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2000.9(2) _cell_formula_units_Z 4 _cell_measurement_temperature 143(1) _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.14 _exptl_crystal_density_diffrn 1.528 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 936 _exptl_absorpt_coefficient_mu 1.621 _exptl_absorpt_correction_type 'multi-scan' _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_correction_T_min 0.7826 _diffrn_ambient_temperature 143(1) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'CCD Area Detector' _diffrn_measurement_device_type 'Rigaku Mercury' _diffrn_measurement_method 'phi and omega rotations' _diffrn_reflns_number 29143 _diffrn_reflns_av_R_equivalents 0.0343 _diffrn_reflns_av_sigmaI/netI 0.0242 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 2.99 _diffrn_reflns_theta_max 27.48 _reflns_number_total 4552 _reflns_number_gt 4291 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku, 1999)' _computing_data_reduction 'CrystalClear (Rigaku, 1999)' _computing_structure_solution 'SIR97 (Altomare, 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0330P)^2^+0.4638P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _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 0.023(15) _refine_ls_number_reflns 4552 _refine_ls_number_parameters 231 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0278 _refine_ls_R_factor_gt 0.0260 _refine_ls_wR_factor_ref 0.0625 _refine_ls_wR_factor_gt 0.0614 _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_symetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group I1 I 0.18165(3) 0.812913(14) 0.825640(10) 0.04360(7) Uani 1 1 d . . . C1 C 0.4148(4) 0.7293(2) 0.86149(12) 0.0296(6) Uani 1 1 d . . . H1 H 0.5379 0.7656 0.8633 0.039 Uiso 1 1 calc R . . C2 C 0.3884(4) 0.65993(19) 0.91490(11) 0.0287(6) Uani 1 1 d . . . H2 H 0.2523 0.6487 0.9269 0.038 Uiso 1 1 calc R . . C3 C 0.5320(4) 0.6558(2) 0.96884(13) 0.0367(7) Uani 1 1 d . . . H3A H 0.4988 0.6012 0.9958 0.049 Uiso 1 1 calc R . . H3B H 0.5210 0.7155 0.9933 0.049 Uiso 1 1 calc R . . C4 C 0.7420(4) 0.6443(2) 0.94654(14) 0.0401(7) Uani 1 1 d . . . H4A H 0.7856 0.7049 0.9274 0.053 Uiso 1 1 calc R . . H4B H 0.8258 0.6307 0.9821 0.053 Uiso 1 1 calc R . . C5 C 0.7572(4) 0.5618(2) 0.89980(13) 0.0375(7) Uani 1 1 d . . . H5A H 0.6995 0.5030 0.9173 0.050 Uiso 1 1 calc R . . H5B H 0.8935 0.5483 0.8912 0.050 Uiso 1 1 calc R . . C6 C 0.6538(4) 0.5878(2) 0.83916(12) 0.0305(6) Uani 1 1 d . . . H6A H 0.6536 0.5312 0.8118 0.041 Uiso 1 1 calc R . . H6B H 0.7248 0.6399 0.8183 0.041 Uiso 1 1 calc R . . C7 C 0.4424(4) 0.62115(18) 0.85047(11) 0.0214(5) Uani 1 1 d . . . C8 C 0.2861(3) 0.56180(18) 0.81884(10) 0.0230(5) Uani 1 1 d . . . H8 H 0.1586 0.5916 0.8270 0.031 Uiso 1 1 calc R . . C9 C 0.1761(4) 0.57835(17) 0.71230(10) 0.0235(5) Uani 1 1 d . . . C10 C 0.2486(3) 0.56680(19) 0.64632(10) 0.0206(5) Uani 1 1 d . . . C11 C 0.3396(4) 0.46707(19) 0.63088(11) 0.0291(5) Uani 1 1 d . . . H11A H 0.2415 0.4160 0.6286 0.039 Uiso 1 1 calc R . . H11B H 0.4378 0.4488 0.6614 0.039 Uiso 1 1 calc R . . C12 C 0.4312(4) 0.4872(2) 0.56613(12) 0.0295(6) Uani 1 1 d . . . H12A H 0.3749 0.4450 0.5344 0.039 Uiso 1 1 calc R . . H12B H 0.5712 0.4772 0.5671 0.039 Uiso 1 1 calc R . . C13 C 0.3811(4) 0.59627(19) 0.55328(11) 0.0240(5) Uani 1 1 d . . . C14 C 0.1628(4) 0.59383(17) 0.54593(11) 0.0255(5) Uani 1 1 d . . . C15 C 0.3958(4) 0.64243(18) 0.61990(10) 0.0223(5) Uani 1 1 d . . . C16 C 0.4897(5) 0.6436(2) 0.49996(12) 0.0376(7) Uani 1 1 d . . . H16A H 0.4568 0.6112 0.4615 0.056 Uiso 1 1 calc R . . H16B H 0.6275 0.6383 0.5071 0.056 Uiso 1 1 calc R . . H16C H 0.4540 0.7115 0.4972 0.056 Uiso 1 1 calc R . . C17 C 0.6003(4) 0.6379(2) 0.64803(12) 0.0336(6) Uani 1 1 d . . . H17A H 0.6881 0.6759 0.6228 0.050 Uiso 1 1 calc R . . H17B H 0.6437 0.5711 0.6492 0.050 Uiso 1 1 calc R . . H17C H 0.5977 0.6640 0.6897 0.050 Uiso 1 1 calc R . . C18 C 0.3193(5) 0.74737(18) 0.62308(12) 0.0317(6) Uani 1 1 d . . . H18A H 0.3242 0.7701 0.6655 0.048 Uiso 1 1 calc R . . H18B H 0.1870 0.7491 0.6084 0.048 Uiso 1 1 calc R . . H18C H 0.3986 0.7889 0.5972 0.048 Uiso 1 1 calc R . . C19 C 0.2818(4) 0.4530(2) 0.83890(11) 0.0360(7) Uani 1 1 d . . . H19A H 0.4091 0.4248 0.8306 0.048 Uiso 1 1 calc R . . H19B H 0.2607 0.4503 0.8837 0.048 Uiso 1 1 calc R . . C20 C 0.1403(6) 0.3940(2) 0.80974(15) 0.0496(9) Uani 1 1 d . . . H20A H 0.0135 0.4221 0.8162 0.074 Uiso 1 1 calc R . . H20B H 0.1440 0.3294 0.8274 0.074 Uiso 1 1 calc R . . H20C H 0.1668 0.3904 0.7657 0.074 Uiso 1 1 calc R . . O1 O 0.3262(3) 0.56407(13) 0.75161(7) 0.0234(3) Uani 1 1 d . . . O2 O 0.0118(3) 0.59686(18) 0.72703(8) 0.0398(5) Uani 1 1 d . . . O3 O 0.0841(2) 0.57618(13) 0.60373(7) 0.0244(4) Uani 1 1 d . . . O4 O 0.0625(3) 0.60235(15) 0.50042(8) 0.0340(4) Uani 1 1 d . . . 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 0.03980(11) 0.03385(10) 0.05715(12) 0.00327(9) -0.01542(10) 0.01127(9) C1 0.0284(14) 0.0254(12) 0.0349(13) 0.0035(11) -0.0110(11) 0.0011(11) C2 0.0287(13) 0.0317(14) 0.0256(12) -0.0006(10) -0.0029(10) 0.0036(11) C3 0.0415(16) 0.0415(16) 0.0270(13) -0.0030(11) -0.0128(12) 0.0013(13) C4 0.0375(16) 0.0417(16) 0.0410(15) 0.0121(13) -0.0217(13) -0.0047(13) C5 0.0247(13) 0.0466(17) 0.0411(15) 0.0121(13) -0.0025(11) 0.0064(12) C6 0.0201(13) 0.0361(14) 0.0352(13) 0.0068(10) 0.0027(11) 0.0023(11) C7 0.0192(12) 0.0225(12) 0.0225(11) 0.0035(9) -0.0015(9) -0.0008(10) C8 0.0243(12) 0.0267(11) 0.0181(10) 0.0030(9) 0.0017(10) 0.0002(10) C9 0.0192(11) 0.0281(12) 0.0232(10) 0.0017(9) -0.0017(10) -0.0016(11) C10 0.0151(10) 0.0264(12) 0.0203(10) 0.0004(9) -0.0006(8) 0.0007(9) C11 0.0329(14) 0.0250(12) 0.0293(12) -0.0003(9) 0.0009(11) 0.0033(11) C12 0.0296(14) 0.0321(14) 0.0267(12) -0.0078(10) 0.0001(11) 0.0065(12) C13 0.0250(12) 0.0275(13) 0.0194(10) -0.0037(9) 0.0023(9) -0.0023(10) C14 0.0328(14) 0.0221(11) 0.0216(10) -0.0031(8) -0.0022(11) 0.0017(11) C15 0.0223(12) 0.0261(12) 0.0187(10) -0.0018(9) 0.0016(9) -0.0017(10) C16 0.0403(17) 0.0504(17) 0.0220(12) -0.0038(12) 0.0072(11) -0.0082(14) C17 0.0209(13) 0.0516(17) 0.0282(12) -0.0038(12) -0.0004(10) -0.0051(12) C18 0.0448(16) 0.0238(12) 0.0265(12) -0.0007(9) -0.0033(13) -0.0022(13) C19 0.0403(17) 0.0426(16) 0.0253(12) 0.0180(11) 0.0048(11) 0.0154(13) C20 0.069(2) 0.0241(14) 0.0557(18) 0.0179(13) 0.0184(16) 0.0055(15) O1 0.0190(8) 0.0333(9) 0.0181(7) 0.0022(7) 0.0011(7) 0.0026(8) O2 0.0174(10) 0.0768(16) 0.0251(9) -0.0037(9) 0.0017(7) 0.0055(10) O3 0.0169(8) 0.0344(10) 0.0218(8) 0.0004(7) -0.0032(7) 0.0000(7) O4 0.0360(11) 0.0418(11) 0.0243(9) -0.0017(8) -0.0109(8) 0.0029(9) _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 C1 2.109(3) . ? C1 C2 1.494(4) . ? C1 C7 1.506(4) . ? C2 C3 1.517(4) . ? C2 C7 1.521(3) . ? C3 C4 1.525(5) . ? C4 C5 1.509(5) . ? C5 C6 1.520(4) . ? C6 C7 1.539(3) . ? C7 C8 1.504(3) . ? C8 O1 1.464(3) . ? C8 C19 1.545(4) . ? C9 O2 1.197(3) . ? C9 O1 1.343(3) . ? C9 C10 1.504(3) . ? C10 O3 1.455(3) . ? C10 C11 1.533(4) . ? C10 C15 1.550(3) . ? C11 C12 1.545(4) . ? C12 C13 1.552(4) . ? C13 C14 1.506(4) . ? C13 C16 1.507(4) . ? C13 C15 1.560(3) . ? C14 O4 1.197(3) . ? C14 O3 1.370(3) . ? C15 C18 1.527(4) . ? C15 C17 1.527(4) . ? C19 C20 1.407(5) . ? 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 C2 C1 C7 60.94(16) . . ? C2 C1 I1 121.9(2) . . ? C7 C1 I1 124.64(19) . . ? C1 C2 C3 121.7(2) . . ? C1 C2 C7 59.92(16) . . ? C3 C2 C7 121.2(2) . . ? C2 C3 C4 112.3(2) . . ? C5 C4 C3 110.5(2) . . ? C4 C5 C6 111.0(2) . . ? C5 C6 C7 112.0(2) . . ? C8 C7 C1 120.6(2) . . ? C8 C7 C2 114.9(2) . . ? C1 C7 C2 59.14(16) . . ? C8 C7 C6 116.2(2) . . ? C1 C7 C6 115.6(2) . . ? C2 C7 C6 118.3(2) . . ? O1 C8 C7 107.23(19) . . ? O1 C8 C19 107.24(19) . . ? C7 C8 C19 114.0(2) . . ? O2 C9 O1 126.0(2) . . ? O2 C9 C10 125.5(2) . . ? O1 C9 C10 108.5(2) . . ? O3 C10 C9 108.72(18) . . ? O3 C10 C11 105.00(19) . . ? C9 C10 C11 115.4(2) . . ? O3 C10 C15 102.61(18) . . ? C9 C10 C15 119.2(2) . . ? C11 C10 C15 104.3(2) . . ? C10 C11 C12 101.6(2) . . ? C11 C12 C13 103.8(2) . . ? C14 C13 C16 114.9(2) . . ? C14 C13 C12 102.6(2) . . ? C16 C13 C12 115.8(2) . . ? C14 C13 C15 99.70(19) . . ? C16 C13 C15 119.0(2) . . ? C12 C13 C15 102.20(19) . . ? O4 C14 O3 121.6(3) . . ? O4 C14 C13 130.9(2) . . ? O3 C14 C13 107.54(19) . . ? C18 C15 C17 109.6(2) . . ? C18 C15 C10 112.6(2) . . ? C17 C15 C10 115.3(2) . . ? C18 C15 C13 113.4(2) . . ? C17 C15 C13 113.7(2) . . ? C10 C15 C13 91.25(18) . . ? C20 C19 C8 116.1(2) . . ? C9 O1 C8 118.27(18) . . ? C14 O3 C10 105.93(18) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.866 _refine_diff_density_min -0.496 _refine_diff_density_rms 0.061