Supplementary Material (ESI) for Organic & Biomolecular Chemistry This journal is (c) The Royal Society of Chemistry 2006 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_Cambridge 0177 _publ_contact_author_name 'Peter Wipf' _publ_contact_author_address ; Department of Chemistry University of Pittsburgh Parkman Av. & University Dr. Pittsburgh PA 15260 UNITED STATES OF AMERICA ; _publ_contact_author_email PWIPF@PITT.EDU _publ_section_title ; Spiroketals via Oxidative Rearrangement of Enol Ethers ; loop_ _publ_author_name 'Peter Wipf' 'Corey R.J Stephenson' 'David Waller' data_compound9 _database_code_depnum_ccdc_archive 'CCDC 624751' _chemical_name_systematic ; (1R*,3S*,6R*)-methyl-2,2-dimethyl-5-oxo-4,7-dioxabicyclo[4.1.0] heptane-3-carboxylate ; _chemical_name_common ; (1R*,3S*,6R*)-methyl-2,2-dimethyl-5-oxo-4,7- dioxabicyclo(4.1.0) heptane-3-carboxylate ; _chemical_formula_sum C9H12O5 _chemical_formula_weight 200.19 _exptl_crystal_colour white _chemical_melting_point nd _exptl_crystal_description needle _exptl_crystal_preparation ethylacetate/hexanes _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.419 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 848 _exptl_absorpt_coefficient_mu 0.117 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9680 _exptl_absorpt_correction_T_max 0.9861 _exptl_absorpt_process_details 'Bruker AXS Sadabs program' _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 2/c' _symmetry_Int_Tables_number 15 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 x,y,z 2 -x,y,1/2-z 3 1/2+x,1/2+y,z 4 1/2-x,1/2+y,1/2-z 5 -x,-y,-z 6 x,-y,1/2+z 7 1/2-x,1/2-y,-z 8 1/2+x,1/2-y,1/2+z _cell_length_a 25.345(17) _cell_length_b 6.038(4) _cell_length_c 12.627(10) _cell_angle_alpha 90.00 _cell_angle_beta 104.129(18) _cell_angle_gamma 90.00 _cell_volume 1874(2) _cell_formula_units_Z 8 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 295(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 AXS Smart CCD' _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 4776 _diffrn_reflns_av_R_equivalents 0.2741 _diffrn_reflns_av_sigmaI/netI 0.2339 _diffrn_reflns_limit_h_min -30 _diffrn_reflns_limit_h_max 25 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.66 _diffrn_reflns_theta_max 25.00 _reflns_number_total 1647 _reflns_number_gt 934 _reflns_threshold_expression >2sigma(I) _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^)+(0.1045P)^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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1647 _refine_ls_number_parameters 130 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1859 _refine_ls_R_factor_gt 0.1225 _refine_ls_wR_factor_ref 0.3053 _refine_ls_wR_factor_gt 0.2742 _refine_ls_goodness_of_fit_ref 1.132 _refine_ls_restrained_S_all 1.132 _refine_ls_shift/su_max 0.000 _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 O1 O 0.1875(2) -0.1574(8) 0.5239(4) 0.0437(14) Uani 1 1 d . . . C1 C 0.1822(3) 0.0000(12) 0.4631(5) 0.0367(17) Uani 1 1 d . . . O2 O 0.23788(17) 0.2448(8) 0.3728(4) 0.0388(13) Uani 1 1 d . . . C2 C 0.2157(3) 0.0322(12) 0.3833(5) 0.0344(17) Uani 1 1 d . . . H2 H 0.2382 -0.0942 0.3732 0.041 Uiso 1 1 calc R . . O3 O 0.14306(18) 0.1441(8) 0.4633(3) 0.0358(13) Uani 1 1 d . . . C3 C 0.1942(3) 0.1664(12) 0.2866(5) 0.0343(17) Uani 1 1 d . . . H3 H 0.2034 0.1202 0.2189 0.041 Uiso 1 1 calc R . . C4 C 0.1397(2) 0.2796(10) 0.2755(5) 0.0250(15) Uani 1 1 d . . . O4 O 0.0437(2) 0.3109(9) 0.4097(6) 0.070(2) Uani 1 1 d . . . O5 O 0.07786(18) 0.6390(7) 0.3879(4) 0.0390(13) Uani 1 1 d . . . C5 C 0.1350(2) 0.3394(10) 0.3924(5) 0.0271(15) Uani 1 1 d . . . H5 H 0.1623 0.4515 0.4236 0.033 Uiso 1 1 calc R . . C6 C 0.1405(3) 0.4928(12) 0.2108(6) 0.046(2) Uani 1 1 d . . . H6A H 0.1687 0.5885 0.2505 0.070 Uiso 1 1 calc R . . H6B H 0.1060 0.5660 0.2001 0.070 Uiso 1 1 calc R . . H6C H 0.1473 0.4578 0.1411 0.070 Uiso 1 1 calc R . . C7 C 0.0958(3) 0.1207(12) 0.2174(6) 0.0391(18) Uani 1 1 d . . . H7A H 0.1048 0.0651 0.1527 0.059 Uiso 1 1 calc R . . H7B H 0.0615 0.1969 0.1975 0.059 Uiso 1 1 calc R . . H7C H 0.0932 -0.0006 0.2650 0.059 Uiso 1 1 calc R . . C8 C 0.0798(3) 0.4208(11) 0.3980(5) 0.0295(15) Uani 1 1 d . . . C9 C 0.0281(3) 0.7423(14) 0.4022(7) 0.051(2) Uani 1 1 d . . . H9A H -0.0017 0.7021 0.3424 0.077 Uiso 1 1 calc R . . H9B H 0.0324 0.9003 0.4041 0.077 Uiso 1 1 calc R . . H9C H 0.0209 0.6926 0.4695 0.077 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 O1 0.042(3) 0.041(3) 0.047(3) 0.016(2) 0.009(2) 0.009(2) C1 0.038(4) 0.043(4) 0.027(4) -0.003(3) 0.003(3) 0.004(4) O2 0.022(2) 0.053(3) 0.043(3) 0.004(2) 0.010(2) -0.006(2) C2 0.031(3) 0.041(4) 0.031(4) 0.002(3) 0.007(3) 0.007(3) O3 0.039(3) 0.038(3) 0.033(3) 0.005(2) 0.012(2) 0.001(2) C3 0.025(3) 0.057(5) 0.023(3) 0.003(3) 0.010(3) 0.005(3) C4 0.024(3) 0.030(4) 0.022(3) -0.003(3) 0.008(3) -0.004(3) O4 0.037(3) 0.050(4) 0.138(6) -0.009(3) 0.046(4) -0.010(3) O5 0.027(3) 0.032(3) 0.065(3) 0.001(2) 0.022(2) 0.003(2) C5 0.023(3) 0.026(3) 0.033(4) 0.003(3) 0.008(3) 0.000(3) C6 0.045(4) 0.048(5) 0.052(5) 0.015(4) 0.024(4) 0.018(4) C7 0.041(4) 0.040(4) 0.035(4) -0.007(3) 0.005(3) 0.000(4) C8 0.031(4) 0.027(4) 0.034(4) -0.006(3) 0.016(3) -0.005(3) C9 0.046(5) 0.046(4) 0.069(6) 0.000(4) 0.026(4) 0.020(4) _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 O1 C1 1.208(8) . ? C1 O3 1.320(8) . ? C1 C2 1.480(10) . ? O2 C2 1.421(8) . ? O2 C3 1.432(8) . ? C2 C3 1.456(9) . ? C2 H2 0.9800 . ? O3 C5 1.465(8) . ? C3 C4 1.515(9) . ? C3 H3 0.9800 . ? C4 C7 1.517(9) . ? C4 C6 1.527(9) . ? C4 C5 1.553(8) . ? O4 C8 1.169(8) . ? O5 C8 1.323(8) . ? O5 C9 1.456(8) . ? C5 C8 1.499(9) . ? C5 H5 0.9800 . ? C6 H6A 0.9600 . ? C6 H6B 0.9600 . ? C6 H6C 0.9600 . ? C7 H7A 0.9600 . ? C7 H7B 0.9600 . ? C7 H7C 0.9600 . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? 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 O3 118.9(6) . . ? O1 C1 C2 122.9(7) . . ? O3 C1 C2 118.1(6) . . ? C2 O2 C3 61.4(4) . . ? O2 C2 C3 59.7(4) . . ? O2 C2 C1 119.2(6) . . ? C3 C2 C1 119.0(6) . . ? O2 C2 H2 115.8 . . ? C3 C2 H2 115.8 . . ? C1 C2 H2 115.8 . . ? C1 O3 C5 121.5(5) . . ? O2 C3 C2 58.9(4) . . ? O2 C3 C4 116.0(5) . . ? C2 C3 C4 118.3(5) . . ? O2 C3 H3 116.9 . . ? C2 C3 H3 116.9 . . ? C4 C3 H3 116.9 . . ? C3 C4 C7 107.7(5) . . ? C3 C4 C6 107.4(5) . . ? C7 C4 C6 112.2(5) . . ? C3 C4 C5 107.3(5) . . ? C7 C4 C5 112.9(5) . . ? C6 C4 C5 109.1(5) . . ? C8 O5 C9 115.3(5) . . ? O3 C5 C8 103.2(5) . . ? O3 C5 C4 111.2(5) . . ? C8 C5 C4 114.3(5) . . ? O3 C5 H5 109.3 . . ? C8 C5 H5 109.3 . . ? C4 C5 H5 109.3 . . ? C4 C6 H6A 109.5 . . ? C4 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C4 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? C4 C7 H7A 109.5 . . ? C4 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C4 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? O4 C8 O5 124.4(6) . . ? O4 C8 C5 126.0(6) . . ? O5 C8 C5 109.6(5) . . ? O5 C9 H9A 109.5 . . ? O5 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? O5 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.406 _refine_diff_density_min -0.398 _refine_diff_density_rms 0.107 # Attachment 'compound_15_rev3.cif' data_compound15 _database_code_depnum_ccdc_archive 'CCDC 624752' _chemical_name_systematic ; (1R*,3S*,5S*,6R*)-methyl-5-hydroxy-2,2,5-trimethyl-4,7- dioxabicyclo[4.1.0]heptane-3-carboxylate ; _chemical_name_common ; (1R*,3S*,5S*,6R*)-methyl-5-hydroxy-2,2,5-trimethyl-4,7- dioxabicyclo(4.1.0)heptane-3-carboxylate ; _chemical_formula_sum C10H16O5 _chemical_formula_weight 216.23 _exptl_crystal_colour white _chemical_melting_point 114.5-116.3 _exptl_crystal_description needle _exptl_crystal_size_max 0.34 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.22 _exptl_crystal_preparation ethylacetate/hexanes _exptl_crystal_density_diffrn 1.318 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 464 _exptl_absorpt_coefficient_mu 0.106 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _computing_data_collection 'Siemens P3/PC' _computing_cell_refinement 'Siemens P3/PC' _computing_data_reduction 'Siemens P3/PC' _computing_molecular_graphics 'Siemens XP' _computing_publication_material 'Siemens XP' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 x,y,z 2 -x,1/2+y,1/2-z 3 -x,-y,-z 4 x,1/2-y,1/2+z _cell_length_a 8.849(2) _cell_length_b 15.512(3) _cell_length_c 8.0902(17) _cell_angle_alpha 90.00 _cell_angle_beta 101.154(19) _cell_angle_gamma 90.00 _cell_volume 1089.5(4) _cell_formula_units_Z 4 _cell_measurement_temperature 208(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 208(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 'Siemens P3' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count 200 _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 2284 _diffrn_reflns_av_R_equivalents 0.0245 _diffrn_reflns_av_sigmaI/netI 0.0512 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -3 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 2.35 _diffrn_reflns_theta_max 26.00 _reflns_number_total 2132 _reflns_number_gt 1408 _reflns_threshold_expression >2sigma(I) _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^)+(0.0554P)^2^+0.8218P] 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 refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2132 _refine_ls_number_parameters 200 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0959 _refine_ls_R_factor_gt 0.0567 _refine_ls_wR_factor_ref 0.1445 _refine_ls_wR_factor_gt 0.1245 _refine_ls_goodness_of_fit_ref 1.032 _refine_ls_restrained_S_all 1.032 _refine_ls_shift/su_max 0.003 _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 O1 O 0.2256(2) 0.79114(12) 0.1214(2) 0.0345(5) Uani 1 1 d . . . C1 C 0.2584(3) 0.97140(18) 0.1849(4) 0.0272(6) Uani 1 1 d . . . H1 H 0.201(3) 0.9564(17) 0.078(4) 0.025(7) Uiso 1 1 d . . . O2 O 0.4175(2) 0.96400(11) 0.1784(2) 0.0283(5) Uani 1 1 d . . . C2 C 0.2162(3) 0.91172(18) 0.3232(3) 0.0283(6) Uani 1 1 d . . . O3 O 0.3308(3) 1.11782(14) 0.2665(3) 0.0517(7) Uani 1 1 d . . . C3 C 0.2732(3) 0.82226(18) 0.2906(4) 0.0302(6) Uani 1 1 d . . . H3 H 0.270(3) 0.7838(16) 0.378(3) 0.012(6) Uiso 1 1 d . . . C4 C 0.3866(3) 0.80822(18) 0.1848(4) 0.0316(7) Uani 1 1 d . . . H4 H 0.453(3) 0.758(2) 0.202(3) 0.034(8) Uiso 1 1 d . . . O4 O 0.0822(2) 1.08403(14) 0.1849(3) 0.0468(6) Uani 1 1 d . . . O5 O 0.4059(2) 0.88161(14) -0.0649(3) 0.0346(5) Uani 1 1 d . . . H5O H 0.462(4) 0.914(2) -0.111(4) 0.045(10) Uiso 1 1 d . . . C5 C 0.4581(3) 0.88404(17) 0.1100(3) 0.0281(6) Uani 1 1 d . . . C6 C 0.2323(3) 1.06554(18) 0.2173(3) 0.0305(6) Uani 1 1 d . . . C7 C 0.2951(4) 0.9402(2) 0.4992(4) 0.0398(8) Uani 1 1 d . . . H7A H 0.273(4) 0.901(2) 0.588(4) 0.054(10) Uiso 1 1 d . . . H7B H 0.411(4) 0.942(2) 0.514(4) 0.049(9) Uiso 1 1 d . . . H7C H 0.257(4) 1.001(2) 0.529(4) 0.059(10) Uiso 1 1 d . . . C8 C 0.0419(4) 0.9064(2) 0.3095(5) 0.0412(8) Uani 1 1 d . . . H8A H 0.017(4) 0.863(2) 0.388(4) 0.047(9) Uiso 1 1 d . . . H8B H -0.004(3) 0.959(2) 0.339(4) 0.035(8) Uiso 1 1 d . . . H8C H -0.008(4) 0.889(2) 0.193(4) 0.044(9) Uiso 1 1 d . . . C9 C 0.6326(4) 0.8799(2) 0.1607(5) 0.0382(7) Uani 1 1 d . . . H9A H 0.665(3) 0.8684(17) 0.282(4) 0.026(7) Uiso 1 1 d . . . H9B H 0.666(4) 0.831(2) 0.110(4) 0.042(9) Uiso 1 1 d . . . H9C H 0.677(4) 0.933(2) 0.127(4) 0.053(10) Uiso 1 1 d . . . C10 C 0.0405(6) 1.1718(3) 0.2188(7) 0.0605(11) Uani 1 1 d . . . H10A H 0.074(5) 1.189(3) 0.332(6) 0.080(14) Uiso 1 1 d . . . H10B H -0.061(7) 1.175(3) 0.193(6) 0.111(19) Uiso 1 1 d . . . H10C H 0.074(5) 1.207(3) 0.140(6) 0.092(17) Uiso 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 O1 0.0359(11) 0.0307(11) 0.0385(12) -0.0066(9) 0.0109(9) -0.0080(9) C1 0.0223(14) 0.0308(15) 0.0290(15) -0.0022(12) 0.0059(11) -0.0013(11) O2 0.0258(10) 0.0242(10) 0.0373(11) -0.0019(8) 0.0120(8) -0.0014(8) C2 0.0289(15) 0.0273(14) 0.0297(15) -0.0003(12) 0.0084(11) -0.0030(11) O3 0.0413(13) 0.0279(11) 0.0873(19) -0.0100(12) 0.0159(12) -0.0019(10) C3 0.0354(16) 0.0264(15) 0.0292(15) 0.0023(13) 0.0072(12) -0.0060(12) C4 0.0308(16) 0.0233(15) 0.0406(17) 0.0014(12) 0.0067(13) 0.0023(12) O4 0.0355(12) 0.0370(12) 0.0656(16) -0.0050(11) 0.0044(11) 0.0127(10) O5 0.0370(12) 0.0371(12) 0.0316(12) -0.0009(9) 0.0116(9) -0.0063(9) C5 0.0278(15) 0.0260(14) 0.0321(16) -0.0026(12) 0.0094(12) 0.0014(11) C6 0.0311(16) 0.0315(15) 0.0305(16) 0.0031(12) 0.0098(12) 0.0015(13) C7 0.046(2) 0.043(2) 0.0319(17) -0.0023(15) 0.0097(14) -0.0078(15) C8 0.0344(17) 0.042(2) 0.052(2) -0.0033(17) 0.0181(16) -0.0060(15) C9 0.0305(17) 0.0374(18) 0.047(2) -0.0019(16) 0.0077(15) 0.0042(14) C10 0.058(3) 0.048(2) 0.074(3) -0.007(2) 0.010(2) 0.025(2) _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 O1 C3 1.435(3) . ? O1 C4 1.442(3) . ? C1 O2 1.423(3) . ? C1 C6 1.510(4) . ? C1 C2 1.553(4) . ? O2 C5 1.432(3) . ? C2 C3 1.517(4) . ? C2 C7 1.525(4) . ? C2 C8 1.527(4) . ? O3 C6 1.201(3) . ? C3 C4 1.456(4) . ? C4 C5 1.516(4) . ? O4 C6 1.334(3) . ? O4 C10 1.451(4) . ? O5 C5 1.401(3) . ? C5 C9 1.521(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 C3 O1 C4 60.81(18) . . ? O2 C1 C6 105.7(2) . . ? O2 C1 C2 110.9(2) . . ? C6 C1 C2 112.6(2) . . ? C1 O2 C5 114.1(2) . . ? C3 C2 C7 108.7(2) . . ? C3 C2 C8 107.6(2) . . ? C7 C2 C8 110.9(3) . . ? C3 C2 C1 106.6(2) . . ? C7 C2 C1 111.7(2) . . ? C8 C2 C1 111.1(2) . . ? O1 C3 C4 59.82(18) . . ? O1 C3 C2 115.3(2) . . ? C4 C3 C2 121.9(2) . . ? O1 C4 C3 59.37(18) . . ? O1 C4 C5 117.4(2) . . ? C3 C4 C5 120.5(2) . . ? C6 O4 C10 116.4(3) . . ? O5 C5 O2 110.8(2) . . ? O5 C5 C4 107.5(2) . . ? O2 C5 C4 111.3(2) . . ? O5 C5 C9 113.0(2) . . ? O2 C5 C9 104.5(2) . . ? C4 C5 C9 109.9(2) . . ? O3 C6 O4 123.4(3) . . ? O3 C6 C1 125.8(3) . . ? O4 C6 C1 110.7(2) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.249 _refine_diff_density_min -0.211 _refine_diff_density_rms 0.053