# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2009 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'D. Boyd' _publ_contact_author_email DR.BOYD@QUB.AC.UK _publ_section_title ; New families of enantiopure cyclohexenone cis-diol, o-quinol dimer and hydrate metabolites from dioxygenase-catalysed dihydroxylation of phenols ; loop_ _publ_author_name 'D. Boyd' 'Christopher C. R. Allen' 'J. Malone' 'Narain D. Sharma' # Attachment '6fs.cif' data_6fs _database_code_depnum_ccdc_archive 'CCDC 721024' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point 100 _chemical_formula_moiety 'C6 H7 I O3' _chemical_formula_sum 'C6 H7 I O3' _chemical_formula_weight 254.02 _chemical_absolute_configuration ad 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 monoclinic _symmetry_space_group_name_H-M P2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 6.368(5) _cell_length_b 7.456(6) _cell_length_c 8.308(6) _cell_angle_alpha 90.00 _cell_angle_beta 100.830(11) _cell_angle_gamma 90.00 _cell_volume 387.4(5) _cell_formula_units_Z 2 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 3461 _cell_measurement_theta_min 3.70 _cell_measurement_theta_max 27.99 _exptl_crystal_description blocks _exptl_crystal_colour colourless _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.178 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 240 _exptl_absorpt_coefficient_mu 4.079 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.162 _exptl_absorpt_correction_T_max 0.291 _exptl_absorpt_process_details 'Bruker SADABS' _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(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 SMART CCD area detector' _diffrn_measurement_method 'phi and omega scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3863 _diffrn_reflns_av_R_equivalents 0.0208 _diffrn_reflns_av_sigmaI/netI 0.0239 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 2.50 _diffrn_reflns_theta_max 27.99 _reflns_number_total 1572 _reflns_number_gt 1545 _reflns_threshold_expression >2sigma(I) _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 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0687P)^2^+0.1909P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _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 0.01(5) _refine_ls_number_reflns 1572 _refine_ls_number_parameters 93 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0323 _refine_ls_R_factor_gt 0.0319 _refine_ls_wR_factor_ref 0.0907 _refine_ls_wR_factor_gt 0.0901 _refine_ls_goodness_of_fit_ref 1.104 _refine_ls_restrained_S_all 1.104 _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 C1 C 0.1193(7) 0.244(2) 0.8050(6) 0.0332(9) Uani 1 1 d . . . O1 O -0.0041(7) 0.2890(6) 0.8961(5) 0.0424(14) Uani 1 1 d . . . C2 C 0.0566(8) 0.2608(15) 0.6262(6) 0.0360(11) Uani 1 1 d . . . H2 H -0.0779 0.3060 0.5819 0.043 Uiso 1 1 calc R . . C3 C 0.1883(8) 0.2128(6) 0.5250(6) 0.0284(12) Uani 1 1 d . . . I3 I 0.09334(4) 0.24920(12) 0.27105(3) 0.03585(15) Uani 1 1 d . . . C4 C 0.4020(8) 0.1183(8) 0.5840(7) 0.0321(11) Uani 1 1 d . . . H4 H 0.3769 -0.0112 0.5868 0.039 Uiso 1 1 calc R . . O4 O 0.5559(6) 0.1524(6) 0.4829(5) 0.0410(10) Uani 1 1 d . . . H4A H 0.5591 0.0674 0.4208 0.061 Uiso 1 1 calc R . . C5 C 0.4979(9) 0.1831(9) 0.7593(8) 0.0310(12) Uani 1 1 d . . . H5 H 0.6257 0.1118 0.8014 0.037 Uiso 1 1 calc R . . O5 O 0.5569(8) 0.3666(8) 0.7592(7) 0.0374(11) Uani 1 1 d . . . H5A H 0.6867 0.3758 0.7889 0.056 Uiso 1 1 calc R . . C6 C 0.3342(9) 0.1557(9) 0.8725(7) 0.0365(13) Uani 1 1 d . . . H6A H 0.3126 0.0283 0.8861 0.044 Uiso 1 1 calc R . . H6B H 0.3915 0.2057 0.9796 0.044 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 C1 0.0266(18) 0.042(3) 0.0306(18) 0.003(7) 0.0029(14) 0.002(5) O1 0.0353(19) 0.059(4) 0.0331(18) 0.0021(18) 0.0061(15) 0.0032(18) C2 0.0269(19) 0.048(3) 0.031(2) 0.008(4) -0.0013(15) 0.001(3) C3 0.027(2) 0.028(4) 0.028(2) 0.0018(17) -0.0006(16) -0.0024(18) I3 0.0417(2) 0.0375(2) 0.02644(19) 0.0004(2) 0.00176(12) 0.00522(19) C4 0.029(2) 0.031(2) 0.036(3) -0.001(2) 0.004(2) 0.002(2) O4 0.0327(19) 0.053(3) 0.039(2) -0.0131(19) 0.0110(18) 0.0010(18) C5 0.027(3) 0.034(3) 0.030(3) 0.004(2) -0.002(2) 0.003(2) O5 0.030(2) 0.036(3) 0.044(3) -0.0037(19) 0.0028(18) -0.0060(19) C6 0.033(3) 0.045(3) 0.029(3) 0.012(2) 0.000(2) 0.000(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 C1 O1 1.235(8) . ? C1 C2 1.469(7) . ? C1 C6 1.527(9) . ? C2 C3 1.343(8) . ? C3 C4 1.529(7) . ? C3 I3 2.100(5) . ? C4 O4 1.428(7) . ? C4 C5 1.547(8) . ? C5 O5 1.419(9) . ? C5 C6 1.543(8) . ? 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 120.9(6) . . ? O1 C1 C6 121.4(5) . . ? C2 C1 C6 117.5(6) . . ? C3 C2 C1 121.8(6) . . ? C2 C3 C4 123.0(5) . . ? C2 C3 I3 119.9(4) . . ? C4 C3 I3 116.9(4) . . ? O4 C4 C3 113.4(5) . . ? O4 C4 C5 107.7(4) . . ? C3 C4 C5 109.1(4) . . ? O5 C5 C6 109.7(5) . . ? O5 C5 C4 111.0(5) . . ? C6 C5 C4 109.9(5) . . ? C1 C6 C5 112.4(5) . . ? 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 C3 180.0(10) . . . . ? C6 C1 C2 C3 -4.7(16) . . . . ? C1 C2 C3 C4 6.9(13) . . . . ? C1 C2 C3 I3 -177.7(8) . . . . ? C2 C3 C4 O4 -152.5(6) . . . . ? I3 C3 C4 O4 32.1(6) . . . . ? C2 C3 C4 C5 -32.4(8) . . . . ? I3 C3 C4 C5 152.2(4) . . . . ? O4 C4 C5 O5 56.4(6) . . . . ? C3 C4 C5 O5 -67.2(6) . . . . ? O4 C4 C5 C6 177.9(5) . . . . ? C3 C4 C5 C6 54.3(6) . . . . ? O1 C1 C6 C5 -155.7(10) . . . . ? C2 C1 C6 C5 28.9(13) . . . . ? O5 C5 C6 C1 68.1(9) . . . . ? C4 C5 C6 C1 -54.2(9) . . . . ? _diffrn_measured_fraction_theta_max 0.914 _diffrn_reflns_theta_full 27.99 _diffrn_measured_fraction_theta_full 0.914 _refine_diff_density_max 0.710 _refine_diff_density_min -0.630 _refine_diff_density_rms 0.117 # Attachment '7d.cif' data_7d _database_code_depnum_ccdc_archive 'CCDC 721025' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point 158 _chemical_formula_moiety 'C18 H24 O6' _chemical_formula_sum 'C18 H24 O6' _chemical_formula_weight 336.37 _chemical_absolute_configuration rm 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' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' _cell_length_a 6.581(8) _cell_length_b 7.123(8) _cell_length_c 11.041(13) _cell_angle_alpha 102.325(16) _cell_angle_beta 96.496(17) _cell_angle_gamma 110.764(16) _cell_volume 462.6(9) _cell_formula_units_Z 1 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 1911 _cell_measurement_theta_min 3.18 _cell_measurement_theta_max 26.69 _exptl_crystal_description plates _exptl_crystal_colour colourless _exptl_crystal_size_max 1.0 _exptl_crystal_size_mid 0.75 _exptl_crystal_size_min 0.40 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.207 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 180 _exptl_absorpt_coefficient_mu 0.090 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.890 _exptl_absorpt_correction_T_max 0.969 _exptl_absorpt_process_details 'Bruker SADABS' _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(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 SMART CCD area detector' _diffrn_measurement_method 'phi and omega scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3590 _diffrn_reflns_av_R_equivalents 0.0121 _diffrn_reflns_av_sigmaI/netI 0.0403 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.93 _diffrn_reflns_theta_max 28.23 _reflns_number_total 3246 _reflns_number_gt 2834 _reflns_threshold_expression >2sigma(I) _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 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0631P)^2^+0.1126P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _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 1.8(14) _refine_ls_number_reflns 3246 _refine_ls_number_parameters 223 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0568 _refine_ls_R_factor_gt 0.0494 _refine_ls_wR_factor_ref 0.1329 _refine_ls_wR_factor_gt 0.1259 _refine_ls_goodness_of_fit_ref 1.045 _refine_ls_restrained_S_all 1.045 _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 C1 C 0.0060(5) 1.0185(4) -0.1099(3) 0.0510(6) Uani 1 1 d . . . O1 O 0.0619(4) 1.2086(3) -0.0872(3) 0.0846(7) Uani 1 1 d . . . C2 C -0.2248(5) 0.8732(4) -0.1658(3) 0.0509(6) Uani 1 1 d . . . H2 H -0.3295 0.9276 -0.1857 0.061 Uiso 1 1 calc R . . C3 C -0.2909(5) 0.6662(4) -0.1893(2) 0.0497(6) Uani 1 1 d . . . C3' C -0.5277(6) 0.5169(6) -0.2518(4) 0.0830(11) Uani 1 1 d . . . H3'1 H -0.5970 0.4504 -0.1918 0.124 Uiso 1 1 calc R . . H3'2 H -0.5265 0.4130 -0.3229 0.124 Uiso 1 1 calc R . . H3'3 H -0.6093 0.5930 -0.2803 0.124 Uiso 1 1 calc R . . C4 C -0.1282(5) 0.5680(4) -0.1583(3) 0.0489(6) Uani 1 1 d . . . H4 H -0.0744 0.5298 -0.2353 0.059 Uiso 1 1 calc R . . O4 O -0.2433(4) 0.3810(3) -0.1260(3) 0.0793(7) Uani 1 1 d . . . H4A H -0.1581 0.3236 -0.1128 0.119 Uiso 1 1 calc R . . C5 C 0.0728(4) 0.7182(4) -0.0556(2) 0.0441(6) Uani 1 1 d . . . H5 H 0.1827 0.6558 -0.0466 0.053 Uiso 1 1 calc R . . O5 O -0.0044(3) 0.7560(3) 0.06392(16) 0.0485(4) Uani 1 1 d . . . C6 C 0.1790(4) 0.9282(4) -0.0859(2) 0.0471(6) Uani 1 1 d . . . H6 H 0.2267 0.8975 -0.1662 0.057 Uiso 1 1 calc R . . C6' C 0.3879(5) 1.0835(6) 0.0118(3) 0.0698(9) Uani 1 1 d . . . H6'1 H 0.4593 1.2009 -0.0195 0.105 Uiso 1 1 calc R . . H6'2 H 0.4881 1.0163 0.0262 0.105 Uiso 1 1 calc R . . H6'3 H 0.3470 1.1303 0.0900 0.105 Uiso 1 1 calc R . . C7 C 0.0908(4) 0.7171(4) 0.1638(2) 0.0470(6) Uani 1 1 d . . . O7 O 0.2440(5) 0.6621(5) 0.1660(2) 0.0907(9) Uani 1 1 d . . . C8 C -0.0190(4) 0.7565(4) 0.2752(2) 0.0467(6) Uani 1 1 d . . . O8 O 0.0962(4) 0.7123(4) 0.3823(2) 0.0715(7) Uani 1 1 d . . . C9 C -0.2632(5) 0.6207(5) 0.2598(3) 0.0642(8) Uani 1 1 d . . . H9A H -0.2847 0.4777 0.2568 0.077 Uiso 1 1 calc R . . H9B H -0.3516 0.6224 0.1838 0.077 Uiso 1 1 calc R . . C10 C -0.3219(5) 0.7278(6) 0.3816(3) 0.0719(9) Uani 1 1 d . . . H10A H -0.3668 0.6339 0.4344 0.086 Uiso 1 1 calc R . . H10B H -0.4402 0.7739 0.3604 0.086 Uiso 1 1 calc R . . C11 C -0.0997(5) 0.9178(5) 0.4493(3) 0.0626(8) Uani 1 1 d . . . C12 C 0.0489(6) 0.8122(7) 0.4898(3) 0.0782(11) Uani 1 1 d . . . O12 O 0.1171(6) 0.7995(7) 0.5929(3) 0.1279(14) Uani 1 1 d . . . C13 C -0.1183(7) 1.0872(8) 0.5547(3) 0.0950(13) Uani 1 1 d . . . H13A H -0.2045 1.0229 0.6102 0.143 Uiso 1 1 calc R . . H13B H -0.1895 1.1641 0.5176 0.143 Uiso 1 1 calc R . . H13C H 0.0275 1.1803 0.6020 0.143 Uiso 1 1 calc R . . C14 C -0.0004(5) 0.9828(4) 0.3349(3) 0.0532(6) Uani 1 1 d . . . C15 C -0.1440(8) 1.0591(6) 0.2533(3) 0.0794(10) Uani 1 1 d . . . H15A H -0.1503 1.1841 0.3033 0.119 Uiso 1 1 calc R . . H15B H -0.2915 0.9531 0.2237 0.119 Uiso 1 1 calc R . . H15C H -0.0796 1.0874 0.1820 0.119 Uiso 1 1 calc R . . C16 C 0.2395(7) 1.1428(7) 0.3761(4) 0.0939(13) Uani 1 1 d . . . H16A H 0.3020 1.1583 0.3025 0.141 Uiso 1 1 calc R . . H16B H 0.3250 1.0959 0.4297 0.141 Uiso 1 1 calc R . . H16C H 0.2421 1.2747 0.4217 0.141 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 C1 0.0635(18) 0.0474(16) 0.0470(14) 0.0191(12) 0.0154(12) 0.0225(13) O1 0.0903(17) 0.0441(12) 0.118(2) 0.0246(12) 0.0148(14) 0.0247(11) C2 0.0571(16) 0.0551(16) 0.0503(15) 0.0212(12) 0.0127(12) 0.0289(13) C3 0.0510(15) 0.0574(16) 0.0379(13) 0.0118(11) 0.0098(10) 0.0186(12) C3' 0.056(2) 0.080(2) 0.091(3) 0.009(2) -0.0037(18) 0.0140(18) C4 0.0584(17) 0.0384(13) 0.0497(15) 0.0090(11) 0.0160(12) 0.0188(12) O4 0.0756(15) 0.0478(12) 0.121(2) 0.0351(13) 0.0275(14) 0.0217(11) C5 0.0505(14) 0.0521(14) 0.0426(13) 0.0182(11) 0.0168(11) 0.0298(12) O5 0.0598(11) 0.0653(11) 0.0381(9) 0.0251(8) 0.0165(7) 0.0368(9) C6 0.0486(14) 0.0505(14) 0.0407(13) 0.0156(11) 0.0125(11) 0.0149(12) C6' 0.0557(18) 0.074(2) 0.0606(18) 0.0209(16) 0.0055(14) 0.0033(15) C7 0.0451(14) 0.0551(15) 0.0404(13) 0.0149(11) 0.0024(10) 0.0200(12) O7 0.0937(19) 0.159(3) 0.0538(12) 0.0297(15) 0.0133(12) 0.089(2) C8 0.0451(14) 0.0599(16) 0.0364(12) 0.0222(11) 0.0025(10) 0.0186(12) O8 0.0759(15) 0.1127(18) 0.0481(11) 0.0426(12) 0.0125(10) 0.0508(14) C9 0.0564(18) 0.0659(18) 0.0585(18) 0.0180(14) 0.0070(14) 0.0110(14) C10 0.0522(17) 0.096(2) 0.0598(18) 0.0256(17) 0.0179(14) 0.0162(16) C11 0.0525(17) 0.092(2) 0.0384(14) 0.0192(14) 0.0103(12) 0.0217(16) C12 0.070(2) 0.131(3) 0.0404(16) 0.0353(17) 0.0126(14) 0.040(2) O12 0.137(3) 0.242(4) 0.0503(15) 0.067(2) 0.0249(16) 0.111(3) C13 0.097(3) 0.133(4) 0.0482(18) 0.007(2) 0.0222(18) 0.045(3) C14 0.0542(16) 0.0579(16) 0.0401(13) 0.0099(11) 0.0107(11) 0.0148(13) C15 0.123(3) 0.084(2) 0.0599(19) 0.0296(17) 0.0315(19) 0.065(2) C16 0.082(3) 0.087(3) 0.065(2) -0.0048(19) 0.0240(18) -0.011(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 C1 O1 1.230(4) . ? C1 C2 1.470(4) . ? C1 C6 1.517(4) . ? C2 C3 1.337(4) . ? C3 C4 1.517(4) . ? C3 C3' 1.518(5) . ? C4 O4 1.422(4) . ? C4 C5 1.523(4) . ? C5 O5 1.472(3) . ? C5 C6 1.538(4) . ? O5 C7 1.335(3) . ? C6 C6' 1.535(4) . ? C7 O7 1.204(4) . ? C7 C8 1.520(4) . ? C8 O8 1.482(3) . ? C8 C9 1.521(4) . ? C8 C14 1.561(4) . ? O8 C12 1.376(5) . ? C9 C10 1.559(5) . ? C10 C11 1.564(5) . ? C11 C12 1.513(5) . ? C11 C13 1.537(5) . ? C11 C14 1.568(4) . ? C12 O12 1.209(4) . ? C14 C16 1.529(5) . ? C14 C15 1.543(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 O1 C1 C2 121.6(3) . . ? O1 C1 C6 120.0(3) . . ? C2 C1 C6 118.3(2) . . ? C3 C2 C1 122.9(3) . . ? C2 C3 C4 121.1(3) . . ? C2 C3 C3' 122.5(3) . . ? C4 C3 C3' 116.4(3) . . ? O4 C4 C3 108.8(2) . . ? O4 C4 C5 112.4(2) . . ? C3 C4 C5 112.4(2) . . ? O5 C5 C4 107.7(2) . . ? O5 C5 C6 108.4(2) . . ? C4 C5 C6 111.4(2) . . ? C7 O5 C5 118.5(2) . . ? C1 C6 C6' 113.1(3) . . ? C1 C6 C5 110.3(2) . . ? C6' C6 C5 113.8(2) . . ? O7 C7 O5 124.9(3) . . ? O7 C7 C8 124.9(2) . . ? O5 C7 C8 110.3(2) . . ? O8 C8 C7 107.2(2) . . ? O8 C8 C9 104.7(2) . . ? C7 C8 C9 117.5(2) . . ? O8 C8 C14 102.2(2) . . ? C7 C8 C14 119.0(2) . . ? C9 C8 C14 104.4(2) . . ? C12 O8 C8 105.9(2) . . ? C8 C9 C10 102.1(2) . . ? C9 C10 C11 103.4(3) . . ? C12 C11 C13 115.7(3) . . ? C12 C11 C10 102.2(3) . . ? C13 C11 C10 115.8(3) . . ? C12 C11 C14 99.7(3) . . ? C13 C11 C14 118.3(3) . . ? C10 C11 C14 102.5(2) . . ? O12 C12 O8 120.9(4) . . ? O12 C12 C11 131.4(4) . . ? O8 C12 C11 107.7(2) . . ? C16 C14 C15 110.5(3) . . ? C16 C14 C8 113.1(3) . . ? C15 C14 C8 114.5(2) . . ? C16 C14 C11 112.5(3) . . ? C15 C14 C11 113.6(3) . . ? C8 C14 C11 91.4(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 C3 -178.8(3) . . . . ? C6 C1 C2 C3 4.1(4) . . . . ? C1 C2 C3 C4 0.3(4) . . . . ? C1 C2 C3 C3' -177.5(3) . . . . ? C2 C3 C4 O4 148.6(3) . . . . ? C3' C3 C4 O4 -33.3(4) . . . . ? C2 C3 C4 C5 23.4(4) . . . . ? C3' C3 C4 C5 -158.6(3) . . . . ? O4 C4 C5 O5 -55.0(3) . . . . ? C3 C4 C5 O5 68.2(3) . . . . ? O4 C4 C5 C6 -173.7(2) . . . . ? C3 C4 C5 C6 -50.5(3) . . . . ? C4 C5 O5 C7 123.9(2) . . . . ? C6 C5 O5 C7 -115.5(2) . . . . ? O1 C1 C6 C6' 23.0(4) . . . . ? C2 C1 C6 C6' -159.8(2) . . . . ? O1 C1 C6 C5 151.6(3) . . . . ? C2 C1 C6 C5 -31.2(3) . . . . ? O5 C5 C6 C1 -64.4(3) . . . . ? C4 C5 C6 C1 53.9(3) . . . . ? O5 C5 C6 C6' 63.9(3) . . . . ? C4 C5 C6 C6' -177.8(2) . . . . ? C5 O5 C7 O7 3.8(4) . . . . ? C5 O5 C7 C8 -177.4(2) . . . . ? O7 C7 C8 O8 -0.6(4) . . . . ? O5 C7 C8 O8 -179.4(2) . . . . ? O7 C7 C8 C9 -118.0(4) . . . . ? O5 C7 C8 C9 63.2(3) . . . . ? O7 C7 C8 C14 114.5(3) . . . . ? O5 C7 C8 C14 -64.3(3) . . . . ? C7 C8 O8 C12 160.5(3) . . . . ? C9 C8 O8 C12 -74.1(3) . . . . ? C14 C8 O8 C12 34.6(3) . . . . ? O8 C8 C9 C10 69.5(3) . . . . ? C7 C8 C9 C10 -171.8(2) . . . . ? C14 C8 C9 C10 -37.6(3) . . . . ? C8 C9 C10 C11 1.5(3) . . . . ? C9 C10 C11 C12 -68.5(3) . . . . ? C9 C10 C11 C13 164.7(3) . . . . ? C9 C10 C11 C14 34.5(3) . . . . ? C8 O8 C12 O12 178.2(4) . . . . ? C8 O8 C12 C11 0.7(4) . . . . ? C13 C11 C12 O12 19.6(7) . . . . ? C10 C11 C12 O12 -107.2(5) . . . . ? C14 C11 C12 O12 147.6(5) . . . . ? C13 C11 C12 O8 -163.3(3) . . . . ? C10 C11 C12 O8 69.9(3) . . . . ? C14 C11 C12 O8 -35.2(4) . . . . ? O8 C8 C14 C16 63.0(3) . . . . ? C7 C8 C14 C16 -54.8(3) . . . . ? C9 C8 C14 C16 171.9(3) . . . . ? O8 C8 C14 C15 -169.2(3) . . . . ? C7 C8 C14 C15 73.1(3) . . . . ? C9 C8 C14 C15 -60.3(3) . . . . ? O8 C8 C14 C11 -52.3(2) . . . . ? C7 C8 C14 C11 -170.0(2) . . . . ? C9 C8 C14 C11 56.6(2) . . . . ? C12 C11 C14 C16 -64.7(4) . . . . ? C13 C11 C14 C16 61.6(4) . . . . ? C10 C11 C14 C16 -169.7(3) . . . . ? C12 C11 C14 C15 168.7(3) . . . . ? C13 C11 C14 C15 -65.0(4) . . . . ? C10 C11 C14 C15 63.7(4) . . . . ? C12 C11 C14 C8 51.1(3) . . . . ? C13 C11 C14 C8 177.4(3) . . . . ? C10 C11 C14 C8 -53.9(3) . . . . ? _diffrn_measured_fraction_theta_max 0.832 _diffrn_reflns_theta_full 28.23 _diffrn_measured_fraction_theta_full 0.832 _refine_diff_density_max 0.180 _refine_diff_density_min -0.157 _refine_diff_density_rms 0.031 # Attachment '12d.cif' data_12d _database_code_depnum_ccdc_archive 'CCDC 721026' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point 128 _chemical_formula_moiety 'C26 H32 O7' _chemical_formula_sum 'C26 H32 O7' _chemical_formula_weight 456.52 _chemical_absolute_configuration rm 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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 6.4039(14) _cell_length_b 13.997(3) _cell_length_c 13.665(2) _cell_angle_alpha 90.00 _cell_angle_beta 101.776(13) _cell_angle_gamma 90.00 _cell_volume 1199.1(4) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 43 _cell_measurement_theta_min 5.24 _cell_measurement_theta_max 12.52 _exptl_crystal_description 'elongated plates' _exptl_crystal_colour colourless _exptl_crystal_size_max 0.70 _exptl_crystal_size_mid 0.60 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.264 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 488 _exptl_absorpt_coefficient_mu 0.091 _exptl_absorpt_correction_type none _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 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker P4 diffractometer' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count 97 _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 3875 _diffrn_reflns_av_R_equivalents 0.0193 _diffrn_reflns_av_sigmaI/netI 0.0378 _diffrn_reflns_limit_h_min -1 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 1 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.11 _diffrn_reflns_theta_max 27.50 _reflns_number_total 3076 _reflns_number_gt 2369 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker XSCANS' _computing_cell_refinement 'Bruker XSCANS' _computing_data_reduction 'Bruker XSCANS' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0531P)^2^+0.1112P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _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 -1.0(13) _refine_ls_number_reflns 3076 _refine_ls_number_parameters 306 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0630 _refine_ls_R_factor_gt 0.0441 _refine_ls_wR_factor_ref 0.1119 _refine_ls_wR_factor_gt 0.1018 _refine_ls_goodness_of_fit_ref 1.045 _refine_ls_restrained_S_all 1.044 _refine_ls_shift/su_max 0.008 _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 0.4183(4) 0.7617(2) 0.87151(18) 0.0360(6) Uani 1 1 d . . . H1 H 0.2655 0.7489 0.8493 0.043 Uiso 1 1 calc R . . C2 C 0.5280(4) 0.7522(2) 0.77994(18) 0.0348(5) Uani 1 1 d . . . H2 H 0.4134 0.7541 0.7202 0.042 Uiso 1 1 calc R . . C3 C 0.6394(5) 0.6557(2) 0.7779(2) 0.0494(8) Uani 1 1 d . . . O3 O 0.7681(5) 0.6581(2) 0.7034(2) 0.0733(8) Uani 1 1 d . . . H3 H 0.8932 0.6485 0.7299 0.110 Uiso 1 1 calc R . . C3' C 0.4761(6) 0.5748(3) 0.7515(3) 0.0628(9) Uani 1 1 d . . . H3'A H 0.4066 0.5800 0.6825 0.094 Uiso 1 1 calc R . . H3'B H 0.3718 0.5796 0.7927 0.094 Uiso 1 1 calc R . . H3'C H 0.5475 0.5143 0.7627 0.094 Uiso 1 1 calc R . . C4 C 0.7816(6) 0.6353(2) 0.8790(3) 0.0607(9) Uani 1 1 d . . . O4 O 0.9660(5) 0.6095(2) 0.8829(3) 0.0972(11) Uani 1 1 d . . . C5 C 0.6787(6) 0.6440(3) 0.9636(3) 0.0635(10) Uani 1 1 d . . . H5 H 0.7353 0.6113 1.0222 0.076 Uiso 1 1 calc R . . C6 C 0.5053(6) 0.6976(2) 0.9598(2) 0.0516(8) Uani 1 1 d . . . C6' C 0.3879(8) 0.7009(3) 1.0454(3) 0.0834(14) Uani 1 1 d . . . H6'A H 0.4570 0.6592 1.0979 0.125 Uiso 1 1 calc R . . H6'B H 0.2432 0.6805 1.0221 0.125 Uiso 1 1 calc R . . H6'C H 0.3891 0.7650 1.0703 0.125 Uiso 1 1 calc R . . C7 C 0.6714(4) 0.8411(2) 0.7738(2) 0.0359(6) Uani 1 1 d . . . H7 H 0.7654 0.8304 0.7266 0.043 Uiso 1 1 calc R . . C8 C 0.4485(4) 0.8689(2) 0.90827(18) 0.0397(6) Uani 1 1 d . . . H8 H 0.3685 0.8821 0.9607 0.048 Uiso 1 1 calc R . . C9 C 0.3771(4) 0.9338(2) 0.81839(19) 0.0378(6) Uani 1 1 d . . . O9 O 0.2253(4) 0.98603(19) 0.80787(17) 0.0602(6) Uani 1 1 d . . . C10 C 0.5228(4) 0.92718(19) 0.74197(19) 0.0350(6) Uani 1 1 d . . . C10' C 0.6370(5) 1.0222(2) 0.7389(2) 0.0484(7) Uani 1 1 d . . . H10A H 0.7360 1.0170 0.6951 0.073 Uiso 1 1 calc R . . H10B H 0.7126 1.0384 0.8050 0.073 Uiso 1 1 calc R . . H10C H 0.5342 1.0711 0.7148 0.073 Uiso 1 1 calc R . . O10 O 0.3735(3) 0.91003(14) 0.64633(12) 0.0373(4) Uani 1 1 d . . . C11 C 0.7983(5) 0.8654(2) 0.8766(2) 0.0465(7) Uani 1 1 d . . . H11 H 0.9466 0.8679 0.8902 0.056 Uiso 1 1 calc R . . C12 C 0.6862(5) 0.8831(2) 0.9463(2) 0.0448(7) Uani 1 1 d . . . C12' C 0.7696(7) 0.9116(3) 1.0526(2) 0.0735(11) Uani 1 1 d . . . H12A H 0.9221 0.9056 1.0678 0.110 Uiso 1 1 calc R . . H12B H 0.7094 0.8708 1.0960 0.110 Uiso 1 1 calc R . . H12C H 0.7307 0.9767 1.0620 0.110 Uiso 1 1 calc R . . C13 C 0.4499(4) 0.9040(2) 0.56162(19) 0.0392(6) Uani 1 1 d . . . O13 O 0.6332(3) 0.9129(2) 0.55687(15) 0.0583(6) Uani 1 1 d . . . C14 C 0.2716(4) 0.8829(2) 0.47341(18) 0.0387(6) Uani 1 1 d . . . O14 O 0.3664(3) 0.88834(18) 0.38469(13) 0.0498(5) Uani 1 1 d . . . C15 C 0.0791(5) 0.9496(2) 0.4528(2) 0.0503(7) Uani 1 1 d . . . H15A H 0.1165 1.0119 0.4304 0.060 Uiso 1 1 calc R . . H15B H 0.0170 0.9572 0.5114 0.060 Uiso 1 1 calc R . . C16 C -0.0737(5) 0.8950(3) 0.3681(2) 0.0576(8) Uani 1 1 d . . . H16A H -0.1021 0.9320 0.3068 0.069 Uiso 1 1 calc R . . H16B H -0.2079 0.8806 0.3874 0.069 Uiso 1 1 calc R . . C17 C 0.0506(5) 0.8016(3) 0.3550(2) 0.0488(7) Uani 1 1 d . . . C18 C 0.2334(5) 0.8388(3) 0.3111(2) 0.0535(8) Uani 1 1 d . . . O18 O 0.2689(4) 0.8316(3) 0.22841(17) 0.0817(9) Uani 1 1 d . . . C19 C -0.0802(7) 0.7229(3) 0.2954(3) 0.0752(11) Uani 1 1 d . . . H19A H -0.1344 0.7448 0.2284 0.113 Uiso 1 1 calc R . . H19B H -0.1971 0.7064 0.3263 0.113 Uiso 1 1 calc R . . H19C H 0.0082 0.6678 0.2936 0.113 Uiso 1 1 calc R . . C20 C 0.1727(4) 0.7805(2) 0.4636(2) 0.0405(6) Uani 1 1 d . . . C21 C 0.0263(5) 0.7581(3) 0.5367(2) 0.0554(8) Uani 1 1 d . . . H21A H -0.0409 0.6972 0.5203 0.083 Uiso 1 1 calc R . . H21B H -0.0809 0.8068 0.5319 0.083 Uiso 1 1 calc R . . H21C H 0.1092 0.7563 0.6037 0.083 Uiso 1 1 calc R . . C22 C 0.3417(6) 0.7021(3) 0.4698(3) 0.0562(8) Uani 1 1 d . . . H22A H 0.4334 0.7030 0.5348 0.084 Uiso 1 1 calc R . . H22B H 0.4248 0.7132 0.4198 0.084 Uiso 1 1 calc R . . H22C H 0.2729 0.6410 0.4585 0.084 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 C1 0.0372(13) 0.0396(14) 0.0331(12) -0.0011(11) 0.0116(10) -0.0069(12) C2 0.0398(13) 0.0341(13) 0.0314(12) 0.0001(11) 0.0091(10) -0.0019(12) C3 0.0631(19) 0.0346(15) 0.0563(19) 0.0006(14) 0.0254(16) 0.0035(15) O3 0.0918(18) 0.0515(14) 0.0937(19) 0.0012(14) 0.0588(16) 0.0137(15) C3' 0.091(3) 0.0374(17) 0.062(2) -0.0084(15) 0.0207(19) -0.0102(18) C4 0.064(2) 0.0368(18) 0.078(2) 0.0047(16) 0.0071(18) 0.0084(16) O4 0.0683(18) 0.076(2) 0.142(3) 0.015(2) 0.0092(18) 0.0291(17) C5 0.082(3) 0.0478(19) 0.054(2) 0.0147(16) -0.0021(18) -0.004(2) C6 0.078(2) 0.0410(16) 0.0348(14) 0.0026(13) 0.0093(15) -0.0151(17) C6' 0.135(4) 0.076(3) 0.0473(19) 0.0086(19) 0.040(2) -0.021(3) C7 0.0364(13) 0.0345(14) 0.0402(14) 0.0019(11) 0.0157(11) 0.0013(12) C8 0.0509(15) 0.0411(15) 0.0302(12) -0.0048(11) 0.0157(12) -0.0005(13) C9 0.0428(14) 0.0345(14) 0.0376(14) -0.0042(11) 0.0120(11) 0.0024(13) O9 0.0639(14) 0.0675(15) 0.0547(12) 0.0071(11) 0.0251(11) 0.0267(13) C10 0.0414(13) 0.0320(13) 0.0342(12) -0.0011(11) 0.0135(10) -0.0002(12) C10' 0.064(2) 0.0348(15) 0.0495(16) -0.0008(13) 0.0196(15) -0.0045(14) O10 0.0411(9) 0.0416(10) 0.0320(8) 0.0009(8) 0.0138(7) 0.0007(9) C11 0.0384(14) 0.0395(16) 0.0590(17) 0.0039(14) 0.0040(13) -0.0061(13) C12 0.0566(16) 0.0338(15) 0.0413(14) -0.0029(12) 0.0036(13) -0.0054(14) C12' 0.093(3) 0.067(2) 0.0501(18) -0.0105(18) -0.0082(18) -0.018(2) C13 0.0461(14) 0.0377(15) 0.0392(13) 0.0005(12) 0.0212(11) 0.0023(13) O13 0.0441(10) 0.0878(18) 0.0479(11) -0.0073(12) 0.0213(9) -0.0056(12) C14 0.0428(14) 0.0437(15) 0.0341(12) 0.0014(12) 0.0185(11) 0.0049(13) O14 0.0529(11) 0.0674(15) 0.0337(9) 0.0009(10) 0.0195(8) -0.0034(11) C15 0.0589(18) 0.0449(17) 0.0501(16) 0.0040(14) 0.0180(14) 0.0142(15) C16 0.0529(17) 0.069(2) 0.0497(16) 0.0035(17) 0.0087(14) 0.0162(18) C17 0.0488(16) 0.0564(19) 0.0398(14) -0.0034(14) 0.0059(13) 0.0040(16) C18 0.0572(18) 0.066(2) 0.0386(15) -0.0005(15) 0.0135(14) 0.0082(18) O18 0.0875(18) 0.123(3) 0.0399(12) -0.0127(14) 0.0254(12) -0.0018(19) C19 0.076(2) 0.078(3) 0.064(2) -0.013(2) -0.003(2) -0.008(2) C20 0.0416(14) 0.0414(16) 0.0390(13) -0.0010(12) 0.0094(12) 0.0022(13) C21 0.0531(17) 0.059(2) 0.0583(18) 0.0094(17) 0.0199(15) -0.0064(17) C22 0.062(2) 0.0444(17) 0.0599(19) -0.0043(15) 0.0074(16) 0.0150(16) _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 C6 1.516(4) . ? C1 C2 1.561(3) . ? C1 C8 1.582(4) . ? C2 C3 1.530(4) . ? C2 C7 1.559(4) . ? C3 O3 1.436(4) . ? C3 C4 1.518(5) . ? C3 C3' 1.533(5) . ? C4 O4 1.225(4) . ? C4 C5 1.448(5) . ? C5 C6 1.332(5) . ? C6 C6' 1.515(5) . ? C7 C11 1.510(4) . ? C7 C10 1.542(4) . ? C8 C12 1.518(4) . ? C8 C9 1.521(4) . ? C9 O9 1.201(3) . ? C9 C10 1.539(3) . ? C10 O10 1.473(3) . ? C10 C10' 1.522(4) . ? O10 C13 1.348(3) . ? C11 C12 1.329(4) . ? C12 C12' 1.495(4) . ? C13 O13 1.195(3) . ? C13 C14 1.511(4) . ? C14 O14 1.464(3) . ? C14 C15 1.526(4) . ? C14 C20 1.562(4) . ? O14 C18 1.366(4) . ? C15 C16 1.555(5) . ? C16 C17 1.560(5) . ? C17 C18 1.513(4) . ? C17 C19 1.516(5) . ? C17 C20 1.558(4) . ? C18 O18 1.202(3) . ? C20 C22 1.531(4) . ? C20 C21 1.535(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 C6 C1 C2 115.8(3) . . ? C6 C1 C8 107.9(2) . . ? C2 C1 C8 106.8(2) . . ? C3 C2 C7 114.9(2) . . ? C3 C2 C1 112.2(2) . . ? C7 C2 C1 109.9(2) . . ? O3 C3 C4 109.0(3) . . ? O3 C3 C2 109.2(2) . . ? C4 C3 C2 110.2(3) . . ? O3 C3 C3' 108.2(3) . . ? C4 C3 C3' 109.2(3) . . ? C2 C3 C3' 110.9(3) . . ? O4 C4 C5 125.5(4) . . ? O4 C4 C3 119.3(4) . . ? C5 C4 C3 115.1(3) . . ? C6 C5 C4 121.9(3) . . ? C5 C6 C6' 121.9(3) . . ? C5 C6 C1 122.2(3) . . ? C6' C6 C1 115.9(3) . . ? C11 C7 C10 105.7(2) . . ? C11 C7 C2 110.0(2) . . ? C10 C7 C2 107.6(2) . . ? C12 C8 C9 108.3(2) . . ? C12 C8 C1 106.4(2) . . ? C9 C8 C1 108.2(2) . . ? O9 C9 C8 124.2(2) . . ? O9 C9 C10 122.9(2) . . ? C8 C9 C10 112.8(2) . . ? O10 C10 C10' 110.3(2) . . ? O10 C10 C9 103.79(19) . . ? C10' C10 C9 109.1(2) . . ? O10 C10 C7 112.0(2) . . ? C10' C10 C7 114.7(2) . . ? C9 C10 C7 106.3(2) . . ? C13 O10 C10 119.24(19) . . ? C12 C11 C7 116.2(2) . . ? C11 C12 C12' 127.5(3) . . ? C11 C12 C8 112.4(2) . . ? C12' C12 C8 120.1(3) . . ? O13 C13 O10 124.9(3) . . ? O13 C13 C14 124.6(2) . . ? O10 C13 C14 110.5(2) . . ? O14 C14 C13 106.1(2) . . ? O14 C14 C15 105.7(2) . . ? C13 C14 C15 118.6(2) . . ? O14 C14 C20 101.9(2) . . ? C13 C14 C20 118.3(2) . . ? C15 C14 C20 104.3(2) . . ? C18 O14 C14 106.4(2) . . ? C14 C15 C16 101.5(3) . . ? C15 C16 C17 103.8(2) . . ? C18 C17 C19 115.1(3) . . ? C18 C17 C20 99.5(2) . . ? C19 C17 C20 119.3(3) . . ? C18 C17 C16 102.2(3) . . ? C19 C17 C16 115.6(3) . . ? C20 C17 C16 102.6(2) . . ? O18 C18 O14 121.8(3) . . ? O18 C18 C17 130.8(3) . . ? O14 C18 C17 107.4(2) . . ? C22 C20 C21 109.7(3) . . ? C22 C20 C17 113.6(3) . . ? C21 C20 C17 113.8(2) . . ? C22 C20 C14 112.5(2) . . ? C21 C20 C14 115.0(2) . . ? C17 C20 C14 91.3(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 C6 C1 C2 C3 22.6(3) . . . . ? C8 C1 C2 C3 142.8(2) . . . . ? C6 C1 C2 C7 -106.6(3) . . . . ? C8 C1 C2 C7 13.6(3) . . . . ? C7 C2 C3 O3 -43.1(3) . . . . ? C1 C2 C3 O3 -169.7(2) . . . . ? C7 C2 C3 C4 76.6(3) . . . . ? C1 C2 C3 C4 -50.0(3) . . . . ? C7 C2 C3 C3' -162.3(2) . . . . ? C1 C2 C3 C3' 71.1(3) . . . . ? O3 C3 C4 O4 -11.4(4) . . . . ? C2 C3 C4 O4 -131.2(4) . . . . ? C3' C3 C4 O4 106.7(4) . . . . ? O3 C3 C4 C5 171.7(3) . . . . ? C2 C3 C4 C5 51.9(4) . . . . ? C3' C3 C4 C5 -70.2(4) . . . . ? O4 C4 C5 C6 159.9(4) . . . . ? C3 C4 C5 C6 -23.4(5) . . . . ? C4 C5 C6 C6' 175.3(4) . . . . ? C4 C5 C6 C1 -7.1(5) . . . . ? C2 C1 C6 C5 6.9(4) . . . . ? C8 C1 C6 C5 -112.7(3) . . . . ? C2 C1 C6 C6' -175.3(3) . . . . ? C8 C1 C6 C6' 65.1(3) . . . . ? C3 C2 C7 C11 -83.7(3) . . . . ? C1 C2 C7 C11 44.0(3) . . . . ? C3 C2 C7 C10 161.6(2) . . . . ? C1 C2 C7 C10 -70.7(3) . . . . ? C6 C1 C8 C12 59.6(3) . . . . ? C2 C1 C8 C12 -65.6(2) . . . . ? C6 C1 C8 C9 175.8(2) . . . . ? C2 C1 C8 C9 50.6(3) . . . . ? C12 C8 C9 O9 -131.1(3) . . . . ? C1 C8 C9 O9 114.0(3) . . . . ? C12 C8 C9 C10 47.9(3) . . . . ? C1 C8 C9 C10 -67.0(3) . . . . ? O9 C9 C10 O10 -52.2(3) . . . . ? C8 C9 C10 O10 128.8(2) . . . . ? O9 C9 C10 C10' 65.3(4) . . . . ? C8 C9 C10 C10' -113.7(3) . . . . ? O9 C9 C10 C7 -170.5(3) . . . . ? C8 C9 C10 C7 10.5(3) . . . . ? C11 C7 C10 O10 -174.7(2) . . . . ? C2 C7 C10 O10 -57.2(2) . . . . ? C11 C7 C10 C10' 58.6(3) . . . . ? C2 C7 C10 C10' 176.1(2) . . . . ? C11 C7 C10 C9 -62.0(3) . . . . ? C2 C7 C10 C9 55.5(3) . . . . ? C10' C10 O10 C13 60.9(3) . . . . ? C9 C10 O10 C13 177.6(2) . . . . ? C7 C10 O10 C13 -68.2(3) . . . . ? C10 C7 C11 C12 58.2(3) . . . . ? C2 C7 C11 C12 -57.7(3) . . . . ? C7 C11 C12 C12' -178.0(3) . . . . ? C7 C11 C12 C8 3.4(4) . . . . ? C9 C8 C12 C11 -57.6(3) . . . . ? C1 C8 C12 C11 58.6(3) . . . . ? C9 C8 C12 C12' 123.7(3) . . . . ? C1 C8 C12 C12' -120.1(3) . . . . ? C10 O10 C13 O13 -1.2(4) . . . . ? C10 O10 C13 C14 178.1(2) . . . . ? O13 C13 C14 O14 -6.9(4) . . . . ? O10 C13 C14 O14 173.9(2) . . . . ? O13 C13 C14 C15 -125.4(3) . . . . ? O10 C13 C14 C15 55.3(3) . . . . ? O13 C13 C14 C20 106.7(3) . . . . ? O10 C13 C14 C20 -72.6(3) . . . . ? C13 C14 O14 C18 159.6(2) . . . . ? C15 C14 O14 C18 -73.6(3) . . . . ? C20 C14 O14 C18 35.2(3) . . . . ? O14 C14 C15 C16 68.9(3) . . . . ? C13 C14 C15 C16 -172.3(2) . . . . ? C20 C14 C15 C16 -38.1(3) . . . . ? C14 C15 C16 C17 2.2(3) . . . . ? C15 C16 C17 C18 -68.6(3) . . . . ? C15 C16 C17 C19 165.6(3) . . . . ? C15 C16 C17 C20 34.1(3) . . . . ? C14 O14 C18 O18 179.3(3) . . . . ? C14 O14 C18 C17 0.1(3) . . . . ? C19 C17 C18 O18 17.1(6) . . . . ? C20 C17 C18 O18 145.8(4) . . . . ? C16 C17 C18 O18 -108.9(4) . . . . ? C19 C17 C18 O14 -163.8(3) . . . . ? C20 C17 C18 O14 -35.1(3) . . . . ? C16 C17 C18 O14 70.1(3) . . . . ? C18 C17 C20 C22 -64.3(3) . . . . ? C19 C17 C20 C22 61.7(4) . . . . ? C16 C17 C20 C22 -169.1(3) . . . . ? C18 C17 C20 C21 169.3(3) . . . . ? C19 C17 C20 C21 -64.8(4) . . . . ? C16 C17 C20 C21 64.4(3) . . . . ? C18 C17 C20 C14 51.1(3) . . . . ? C19 C17 C20 C14 177.0(3) . . . . ? C16 C17 C20 C14 -53.8(2) . . . . ? O14 C14 C20 C22 63.4(3) . . . . ? C13 C14 C20 C22 -52.4(3) . . . . ? C15 C14 C20 C22 173.3(3) . . . . ? O14 C14 C20 C21 -170.0(2) . . . . ? C13 C14 C20 C21 74.2(3) . . . . ? C15 C14 C20 C21 -60.2(3) . . . . ? O14 C14 C20 C17 -52.8(2) . . . . ? C13 C14 C20 C17 -168.6(2) . . . . ? C15 C14 C20 C17 57.0(2) . . . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.140 _refine_diff_density_min -0.181 _refine_diff_density_rms 0.037