Supplementary Material (ESI) for Chemical Communications This journal is (c) The Royal Society of Chemistry 2003 data_global _journal_coden_Cambridge 182 loop_ _publ_author_name 'Andrew V. Stachulski' 'Jamie F. Bickley' 'Jennifer A. Cottrell' 'R. Field' 'John R. Harding' 'David L. Hughes' 'K. P. Ravindranathan Kartha' 'Fedor Scheinmann' _publ_contact_author_name 'Dr Andrew V Stachulski' _publ_contact_author_address ; Department of Chemistry University of Liverpool The Robert Robinson Laboratories Liverpool L69 7ZD UNITED KINGDOM ; _publ_contact_author_email STACHULS@LIV.AC.UK _publ_requested_journal 'Chemical Communications' _publ_section_title ; Preparation, X-ray structure and reactivity of a stable glycosyl iodide ; data_jc1m _database_code_CSD 205813 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H35 I O9' _chemical_formula_weight 570.40 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' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 9.6982(16) _cell_length_b 11.4712(19) _cell_length_c 22.658(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2520.7(7) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _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 ? _exptl_crystal_density_diffrn 1.503 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1168 _exptl_absorpt_coefficient_mu 1.317 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.6934 _exptl_absorpt_correction_T_max 0.8796 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 Apex CCD area detector' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4595 _diffrn_reflns_av_R_equivalents 0.0413 _diffrn_reflns_av_sigmaI/netI 0.0328 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 7 _diffrn_reflns_theta_min 1.80 _diffrn_reflns_theta_max 25.03 _reflns_number_total 3911 _reflns_number_gt 3718 _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^)+(0.0312P)^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 0.006(16) _refine_ls_number_reflns 3911 _refine_ls_number_parameters 299 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0226 _refine_ls_R_factor_gt 0.0212 _refine_ls_wR_factor_ref 0.0525 _refine_ls_wR_factor_gt 0.0520 _refine_ls_goodness_of_fit_ref 0.993 _refine_ls_restrained_S_all 0.993 _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 C1 C 0.1464(3) 0.3295(3) 0.83487(13) 0.0164(6) Uani 1 1 d . . . H1 H 0.1220 0.4048 0.8152 0.020 Uiso 1 1 calc R . . C2 C 0.0125(3) 0.2664(2) 0.84726(13) 0.0159(6) Uani 1 1 d . . . H2 H -0.0460 0.2692 0.8110 0.019 Uiso 1 1 calc R . . C3 C -0.1313(3) 0.4171(2) 0.88779(14) 0.0184(7) Uani 1 1 d . . . C4 C -0.2239(3) 0.4446(2) 0.93992(13) 0.0187(7) Uani 1 1 d . . . C5 C -0.2899(4) 0.5641(3) 0.93056(15) 0.0304(8) Uani 1 1 d . . . H5A H -0.3493 0.5827 0.9642 0.046 Uiso 1 1 calc R . . H5B H -0.3451 0.5630 0.8943 0.046 Uiso 1 1 calc R . . H5C H -0.2175 0.6234 0.9271 0.046 Uiso 1 1 calc R . . C6 C -0.1378(4) 0.4450(3) 0.99680(15) 0.0296(8) Uani 1 1 d . . . H6A H -0.0941 0.3687 1.0020 0.044 Uiso 1 1 calc R . . H6B H -0.1979 0.4612 1.0306 0.044 Uiso 1 1 calc R . . H6C H -0.0666 0.5054 0.9941 0.044 Uiso 1 1 calc R . . C7 C -0.3346(3) 0.3498(3) 0.94459(15) 0.0230(8) Uani 1 1 d . . . H7A H -0.2910 0.2751 0.9540 0.034 Uiso 1 1 calc R . . H7B H -0.3837 0.3434 0.9069 0.034 Uiso 1 1 calc R . . H7C H -0.4001 0.3704 0.9758 0.034 Uiso 1 1 calc R . . C8 C 0.0364(3) 0.1397(2) 0.86374(12) 0.0143(6) Uani 1 1 d . . . H8 H 0.0725 0.1349 0.9050 0.017 Uiso 1 1 calc R . . C9 C -0.1398(3) 0.0225(3) 0.90829(13) 0.0170(6) Uani 1 1 d . . . C10 C -0.2730(3) -0.0419(2) 0.89482(12) 0.0177(6) Uani 1 1 d . . . C11 C -0.3858(3) 0.0487(3) 0.88172(15) 0.0213(7) Uani 1 1 d . . . H11A H -0.3965 0.1005 0.9158 0.032 Uiso 1 1 calc R . . H11B H -0.4732 0.0087 0.8740 0.032 Uiso 1 1 calc R . . H11C H -0.3594 0.0947 0.8471 0.032 Uiso 1 1 calc R . . C12 C -0.3124(3) -0.1140(3) 0.94881(14) 0.0216(7) Uani 1 1 d . . . H12A H -0.2361 -0.1662 0.9592 0.032 Uiso 1 1 calc R . . H12B H -0.3947 -0.1604 0.9399 0.032 Uiso 1 1 calc R . . H12C H -0.3318 -0.0619 0.9821 0.032 Uiso 1 1 calc R . . C13 C -0.2533(3) -0.1198(3) 0.84059(12) 0.0239(6) Uani 1 1 d . . . H13A H -0.2322 -0.0713 0.8062 0.036 Uiso 1 1 calc R . . H13B H -0.3381 -0.1640 0.8332 0.036 Uiso 1 1 calc R . . H13C H -0.1770 -0.1740 0.8477 0.036 Uiso 1 1 calc R . . C14 C 0.1359(3) 0.0796(2) 0.82196(13) 0.0152(6) Uani 1 1 d . . . H14 H 0.0906 0.0648 0.7830 0.018 Uiso 1 1 calc R . . C15 C 0.1373(3) -0.1296(3) 0.82190(12) 0.0158(6) Uani 1 1 d . . . C16 C 0.1937(3) -0.2374(3) 0.85274(14) 0.0187(7) Uani 1 1 d . . . C17 C 0.3366(4) -0.2171(3) 0.87847(16) 0.0285(8) Uani 1 1 d . . . H17A H 0.3993 -0.1916 0.8471 0.043 Uiso 1 1 calc R . . H17B H 0.3709 -0.2898 0.8958 0.043 Uiso 1 1 calc R . . H17C H 0.3315 -0.1569 0.9091 0.043 Uiso 1 1 calc R . . C18 C 0.2004(4) -0.3370(3) 0.80771(16) 0.0315(9) Uani 1 1 d . . . H18A H 0.1071 -0.3555 0.7940 0.047 Uiso 1 1 calc R . . H18B H 0.2413 -0.4060 0.8263 0.047 Uiso 1 1 calc R . . H18C H 0.2571 -0.3130 0.7740 0.047 Uiso 1 1 calc R . . C19 C 0.0919(4) -0.2681(3) 0.90192(15) 0.0345(9) Uani 1 1 d . . . H19A H 0.0814 -0.2011 0.9284 0.052 Uiso 1 1 calc R . . H19B H 0.1269 -0.3350 0.9243 0.052 Uiso 1 1 calc R . . H19C H 0.0023 -0.2877 0.8846 0.052 Uiso 1 1 calc R . . C20 C 0.2650(3) 0.1519(2) 0.81377(12) 0.0170(6) Uani 1 1 d . . . H20 H 0.3147 0.1562 0.8524 0.020 Uiso 1 1 calc R . . C21 C 0.3663(3) 0.1092(3) 0.76658(13) 0.0191(7) Uani 1 1 d . . . C22 C 0.4690(4) -0.0550(3) 0.72343(15) 0.0296(8) Uani 1 1 d . . . H22A H 0.4434 -0.0325 0.6832 0.044 Uiso 1 1 calc R . . H22B H 0.4683 -0.1402 0.7268 0.044 Uiso 1 1 calc R . . H22C H 0.5616 -0.0256 0.7323 0.044 Uiso 1 1 calc R . . I1 I 0.258224(19) 0.373596(15) 0.916714(7) 0.01969(6) Uani 1 1 d . . . O1 O 0.2298(2) 0.26782(15) 0.79577(8) 0.0171(4) Uani 1 1 d . . . O2 O -0.0658(2) 0.31278(16) 0.89595(9) 0.0171(5) Uani 1 1 d . . . O3 O -0.1148(2) 0.47528(18) 0.84462(10) 0.0278(5) Uani 1 1 d . . . O4 O -0.0930(2) 0.07940(16) 0.85986(9) 0.0159(5) Uani 1 1 d . . . O5 O -0.0817(2) 0.0248(2) 0.95504(9) 0.0290(5) Uani 1 1 d . . . O6 O 0.1743(2) -0.02929(17) 0.84958(9) 0.0149(4) Uani 1 1 d . . . O7 O 0.0640(2) -0.13116(19) 0.77906(9) 0.0228(4) Uani 1 1 d . . . O8 O 0.4367(3) 0.17171(18) 0.73774(12) 0.0401(7) Uani 1 1 d . . . O9 O 0.3711(2) -0.00571(17) 0.76483(9) 0.0244(5) 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 C1 0.0179(16) 0.0141(14) 0.0171(16) -0.0025(12) -0.0012(12) 0.0012(13) C2 0.0225(16) 0.0137(14) 0.0114(15) -0.0017(12) 0.0027(12) 0.0027(13) C3 0.0168(16) 0.0164(14) 0.0220(17) -0.0010(13) -0.0025(13) -0.0022(14) C4 0.0182(17) 0.0184(14) 0.0196(14) -0.0038(11) 0.0009(12) 0.0030(14) C5 0.034(2) 0.0202(16) 0.037(2) -0.0021(14) 0.0124(15) 0.0080(15) C6 0.0231(17) 0.039(2) 0.0263(19) -0.0119(16) -0.0002(14) -0.0059(17) C7 0.0235(17) 0.0250(19) 0.0204(17) -0.0030(13) 0.0023(13) 0.0015(15) C8 0.0152(13) 0.0122(14) 0.0155(14) 0.0019(12) -0.0009(11) -0.0040(14) C9 0.0183(15) 0.0158(15) 0.0167(17) 0.0026(13) 0.0033(13) -0.0002(13) C10 0.0188(17) 0.0164(13) 0.0178(14) -0.0012(11) 0.0015(12) -0.0008(15) C11 0.0176(16) 0.0192(16) 0.0271(19) 0.0030(14) 0.0014(13) -0.0008(14) C12 0.0225(16) 0.0183(15) 0.0241(17) 0.0003(14) 0.0011(12) -0.0019(15) C13 0.0198(14) 0.0270(14) 0.0248(15) -0.0074(12) 0.0015(14) -0.005(2) C14 0.0190(16) 0.0130(13) 0.0135(15) 0.0023(11) -0.0012(12) 0.0020(13) C15 0.0168(14) 0.0155(14) 0.0151(14) -0.0006(14) 0.0030(11) -0.0030(15) C16 0.0209(16) 0.0138(14) 0.0214(18) 0.0011(13) 0.0013(13) 0.0011(13) C17 0.0283(19) 0.0144(15) 0.043(2) 0.0040(16) -0.0080(16) -0.0006(16) C18 0.045(2) 0.0160(15) 0.034(2) -0.0016(14) -0.0081(16) 0.0000(15) C19 0.033(2) 0.037(2) 0.033(2) 0.0190(16) 0.0056(16) 0.0051(18) C20 0.0189(15) 0.0134(13) 0.0186(14) 0.0038(10) -0.0004(13) -0.0019(14) C21 0.0188(15) 0.0170(15) 0.0215(16) 0.0039(13) -0.0005(12) 0.0033(14) C22 0.0332(19) 0.0270(17) 0.0285(19) -0.0044(15) 0.0107(15) 0.0081(16) I1 0.02042(10) 0.01768(9) 0.02097(10) -0.00087(7) -0.00237(9) -0.00150(10) O1 0.0204(12) 0.0124(9) 0.0186(10) 0.0032(7) 0.0042(9) 0.0018(10) O2 0.0203(11) 0.0137(10) 0.0172(11) 0.0005(8) 0.0042(8) 0.0035(9) O3 0.0381(15) 0.0207(11) 0.0246(13) 0.0042(10) 0.0048(10) 0.0076(11) O4 0.0151(10) 0.0176(10) 0.0152(11) 0.0020(8) 0.0004(8) -0.0033(9) O5 0.0286(13) 0.0433(14) 0.0153(12) 0.0063(10) -0.0036(10) -0.0162(12) O6 0.0182(11) 0.0109(9) 0.0156(11) 0.0021(8) -0.0004(9) -0.0012(9) O7 0.0300(11) 0.0192(10) 0.0192(11) -0.0015(10) -0.0058(9) -0.0012(11) O8 0.0470(16) 0.0223(11) 0.0512(17) 0.0115(11) 0.0313(14) 0.0052(12) O9 0.0287(13) 0.0171(10) 0.0274(13) -0.0039(9) 0.0105(10) 0.0008(10) _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 C1 O1 1.393(3) . ? C1 C2 1.513(4) . ? C1 I1 2.207(3) . ? C2 O2 1.441(3) . ? C2 C8 1.518(4) . ? C3 O3 1.195(4) . ? C3 O2 1.368(3) . ? C3 C4 1.517(4) . ? C4 C5 1.528(4) . ? C4 C7 1.532(5) . ? C4 C6 1.536(4) . ? C8 O4 1.436(3) . ? C8 C14 1.517(4) . ? C9 O5 1.200(4) . ? C9 O4 1.355(3) . ? C9 C10 1.519(4) . ? C10 C12 1.526(4) . ? C10 C13 1.531(4) . ? C10 C11 1.538(4) . ? C14 O6 1.446(3) . ? C14 C20 1.513(4) . ? C15 O7 1.204(3) . ? C15 O6 1.359(4) . ? C15 C16 1.521(4) . ? C16 C17 1.521(4) . ? C16 C19 1.530(4) . ? C16 C18 1.533(4) . ? C20 O1 1.432(3) . ? C20 C21 1.532(4) . ? C21 O8 1.186(4) . ? C21 O9 1.319(3) . ? C22 O9 1.450(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 O1 C1 C2 111.9(2) . . ? O1 C1 I1 111.43(19) . . ? C2 C1 I1 112.1(2) . . ? O2 C2 C1 114.7(2) . . ? O2 C2 C8 104.2(2) . . ? C1 C2 C8 111.9(2) . . ? O3 C3 O2 122.5(3) . . ? O3 C3 C4 126.9(3) . . ? O2 C3 C4 110.6(2) . . ? C3 C4 C5 109.0(3) . . ? C3 C4 C7 108.8(2) . . ? C5 C4 C7 110.7(3) . . ? C3 C4 C6 109.4(3) . . ? C5 C4 C6 110.0(3) . . ? C7 C4 C6 109.0(3) . . ? O4 C8 C14 107.4(2) . . ? O4 C8 C2 108.2(2) . . ? C14 C8 C2 112.3(2) . . ? O5 C9 O4 123.2(3) . . ? O5 C9 C10 126.0(3) . . ? O4 C9 C10 110.9(2) . . ? C9 C10 C12 108.4(2) . . ? C9 C10 C13 109.8(2) . . ? C12 C10 C13 111.0(2) . . ? C9 C10 C11 108.3(2) . . ? C12 C10 C11 110.1(2) . . ? C13 C10 C11 109.2(3) . . ? O6 C14 C20 108.2(2) . . ? O6 C14 C8 106.6(2) . . ? C20 C14 C8 110.7(2) . . ? O7 C15 O6 122.7(3) . . ? O7 C15 C16 124.8(3) . . ? O6 C15 C16 112.4(2) . . ? C17 C16 C15 112.3(3) . . ? C17 C16 C19 110.1(3) . . ? C15 C16 C19 106.8(3) . . ? C17 C16 C18 109.3(3) . . ? C15 C16 C18 108.4(3) . . ? C19 C16 C18 109.9(3) . . ? O1 C20 C14 110.3(2) . . ? O1 C20 C21 104.5(2) . . ? C14 C20 C21 116.2(2) . . ? O8 C21 O9 124.6(3) . . ? O8 C21 C20 124.0(3) . . ? O9 C21 C20 111.3(2) . . ? C1 O1 C20 115.4(2) . . ? C3 O2 C2 117.7(2) . . ? C9 O4 C8 118.4(2) . . ? C15 O6 C14 117.6(2) . . ? C21 O9 C22 115.6(2) . . ? 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 O1 C1 C2 O2 168.0(2) . . . . ? I1 C1 C2 O2 42.0(3) . . . . ? O1 C1 C2 C8 49.6(3) . . . . ? I1 C1 C2 C8 -76.4(3) . . . . ? O3 C3 C4 C5 -2.9(4) . . . . ? O2 C3 C4 C5 177.3(2) . . . . ? O3 C3 C4 C7 117.8(3) . . . . ? O2 C3 C4 C7 -61.9(3) . . . . ? O3 C3 C4 C6 -123.2(3) . . . . ? O2 C3 C4 C6 57.0(3) . . . . ? O2 C2 C8 O4 70.2(3) . . . . ? C1 C2 C8 O4 -165.4(2) . . . . ? O2 C2 C8 C14 -171.5(2) . . . . ? C1 C2 C8 C14 -47.1(3) . . . . ? O5 C9 C10 C12 -6.1(4) . . . . ? O4 C9 C10 C12 174.2(2) . . . . ? O5 C9 C10 C13 -127.5(3) . . . . ? O4 C9 C10 C13 52.8(3) . . . . ? O5 C9 C10 C11 113.4(3) . . . . ? O4 C9 C10 C11 -66.3(3) . . . . ? O4 C8 C14 O6 -74.1(3) . . . . ? C2 C8 C14 O6 167.1(2) . . . . ? O4 C8 C14 C20 168.3(2) . . . . ? C2 C8 C14 C20 49.5(3) . . . . ? O7 C15 C16 C17 146.5(3) . . . . ? O6 C15 C16 C17 -36.1(3) . . . . ? O7 C15 C16 C19 -92.7(3) . . . . ? O6 C15 C16 C19 84.7(3) . . . . ? O7 C15 C16 C18 25.6(4) . . . . ? O6 C15 C16 C18 -156.9(3) . . . . ? O6 C14 C20 O1 -170.3(2) . . . . ? C8 C14 C20 O1 -53.8(3) . . . . ? O6 C14 C20 C21 71.0(3) . . . . ? C8 C14 C20 C21 -172.4(2) . . . . ? O1 C20 C21 O8 25.9(4) . . . . ? C14 C20 C21 O8 147.6(3) . . . . ? O1 C20 C21 O9 -158.0(2) . . . . ? C14 C20 C21 O9 -36.3(4) . . . . ? C2 C1 O1 C20 -57.3(3) . . . . ? I1 C1 O1 C20 69.1(3) . . . . ? C14 C20 O1 C1 59.6(3) . . . . ? C21 C20 O1 C1 -174.9(2) . . . . ? O3 C3 O2 C2 -7.5(4) . . . . ? C4 C3 O2 C2 172.2(2) . . . . ? C1 C2 O2 C3 72.7(3) . . . . ? C8 C2 O2 C3 -164.6(2) . . . . ? O5 C9 O4 C8 3.8(4) . . . . ? C10 C9 O4 C8 -176.5(2) . . . . ? C14 C8 O4 C9 115.2(3) . . . . ? C2 C8 O4 C9 -123.4(3) . . . . ? O7 C15 O6 C14 -7.1(4) . . . . ? C16 C15 O6 C14 175.4(2) . . . . ? C20 C14 O6 C15 -124.8(3) . . . . ? C8 C14 O6 C15 116.0(3) . . . . ? O8 C21 O9 C22 -1.1(5) . . . . ? C20 C21 O9 C22 -177.2(2) . . . . ? _diffrn_measured_fraction_theta_max 0.937 _diffrn_reflns_theta_full 25.03 _diffrn_measured_fraction_theta_full 0.937 _refine_diff_density_max 0.672 _refine_diff_density_min -0.414 _refine_diff_density_rms 0.058