# Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is (c) The Royal Society of Chemistry 2009 data_global _journal_coden_Cambridge 177 loop_ _publ_author_name 'G Pattenden' 'Yi Li.' 'Christopher C. Nawrat' 'Johan M. Winne' _publ_contact_author_name 'G Pattenden' _publ_contact_author_email GP@NOTTINGHAM.AC.UK _publ_section_title ; A Concise Total Synthesis of (+-)-Anthecularin ; # Attachment 'hpbnoo.cif' data_hpbnoo _database_code_depnum_ccdc_archive 'CCDC 707835' _refine_special_details ; All CH3 groups were refined as rigid rotors. ; _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C15 H16 O4' _chemical_formula_sum 'C15 H16 O4' _chemical_formula_weight 260.28 _chemical_absolute_configuration unk 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 0.0000 '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 0.0000 '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_space_group_name_Hall 'P 2ac 2ab' 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 6.5457(9) _cell_length_b 12.2932(15) _cell_length_c 30.973(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2492.4(6) _cell_formula_units_Z 8 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 1284 _cell_measurement_theta_min 2.63 _cell_measurement_theta_max 24.91 _exptl_crystal_description BLOCK _exptl_crystal_colour COLOURLESS _exptl_crystal_size_max 0.17 _exptl_crystal_size_mid 0.06 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.387 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1104 _exptl_absorpt_coefficient_mu 0.100 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8488 _exptl_absorpt_correction_T_max 0.9898 _exptl_absorpt_process_details 'SADABS 2007/2' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 APEX CCD area detector' _diffrn_measurement_method omega _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 9754 _diffrn_reflns_av_R_equivalents 0.0619 _diffrn_reflns_av_sigmaI/netI 0.0597 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 36 _diffrn_reflns_theta_min 2.12 _diffrn_reflns_theta_max 25.05 _reflns_number_total 2559 _reflns_number_gt 2348 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART version 5.625 (Bruker, 2001)' _computing_cell_refinement 'Bruker SAINT version 6.36A (Bruker, 2002)' _computing_data_reduction 'Bruker SAINT; SHELXTL (Sheldrick, 2008)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ' ?' _computing_publication_material 'enCIFer(Allen et al.,2004);PLATON(Spek,2003)' _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^)+(0.0197P)^2^+4.4116P] 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 2559 _refine_ls_number_parameters 347 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0910 _refine_ls_R_factor_gt 0.0809 _refine_ls_wR_factor_ref 0.1433 _refine_ls_wR_factor_gt 0.1401 _refine_ls_goodness_of_fit_ref 1.293 _refine_ls_restrained_S_all 1.293 _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 0.6274(10) 0.4037(5) 0.7488(2) 0.0200(15) Uani 1 1 d . . . O1 O 0.4455(7) 0.4192(4) 0.75003(14) 0.0233(11) Uani 1 1 d . . . O2 O 0.7412(7) 0.4461(3) 0.71713(14) 0.0250(11) Uani 1 1 d . . . C2 C 0.7541(9) 0.3382(5) 0.77977(18) 0.0136(13) Uani 1 1 d . . . C3 C 0.9738(10) 0.3487(5) 0.76269(19) 0.0183(14) Uani 1 1 d . . . H3A H 1.0608 0.3884 0.7840 0.022 Uiso 1 1 calc R . . C4 C 1.0458(10) 0.2283(5) 0.75856(19) 0.0165(14) Uani 1 1 d . . . H4A H 1.1904 0.2210 0.7685 0.020 Uiso 1 1 calc R . . O3 O 0.9114(6) 0.1693(3) 0.78667(13) 0.0172(9) Uani 1 1 d . . . C5 C 1.0218(10) 0.1807(4) 0.71392(19) 0.0160(13) Uani 1 1 d . . . O4 O 1.1661(7) 0.1606(4) 0.69065(14) 0.0240(11) Uani 1 1 d . . . C6 C 0.8060(10) 0.1644(5) 0.70010(19) 0.0158(13) Uani 1 1 d . . . C7 C 0.6627(10) 0.1821(5) 0.72985(19) 0.0178(14) Uani 1 1 d . . . H7A H 0.5233 0.1753 0.7217 0.021 Uiso 1 1 calc R . . C8 C 0.7123(9) 0.2128(5) 0.77606(19) 0.0132(13) Uani 1 1 d . . . C9 C 0.5577(9) 0.1700(5) 0.80700(19) 0.0181(14) Uani 1 1 d . . . H9A H 0.5221 0.0953 0.8047 0.022 Uiso 1 1 calc R . . C10 C 0.4662(10) 0.2274(5) 0.83732(18) 0.0169(13) Uani 1 1 d . . . C11 C 0.5236(10) 0.3444(5) 0.84523(19) 0.0242(15) Uani 1 1 d . . . H11A H 0.5246 0.3579 0.8767 0.029 Uiso 1 1 calc R . . H11B H 0.4178 0.3919 0.8323 0.029 Uiso 1 1 calc R . . C12 C 0.7290(10) 0.3752(5) 0.82688(19) 0.0178(14) Uani 1 1 d . . . H12A H 0.8380 0.3419 0.8447 0.021 Uiso 1 1 calc R . . H12B H 0.7454 0.4552 0.8284 0.021 Uiso 1 1 calc R . . C13 C 0.9563(10) 0.4140(5) 0.7209(2) 0.0215(14) Uani 1 1 d . . . H13A H 1.0452 0.4791 0.7221 0.026 Uiso 1 1 calc R . . H13B H 0.9977 0.3691 0.6959 0.026 Uiso 1 1 calc R . . C14 C 0.7646(10) 0.1318(5) 0.65467(19) 0.0249(16) Uani 1 1 d . . . H14A H 0.6175 0.1207 0.6508 0.037 Uiso 1 1 calc R . . H14B H 0.8372 0.0640 0.6482 0.037 Uiso 1 1 calc R . . H14C H 0.8118 0.1891 0.6351 0.037 Uiso 1 1 calc R . . C15 C 0.2937(10) 0.1829(6) 0.8641(2) 0.0262(16) Uani 1 1 d . . . H15A H 0.2646 0.1080 0.8552 0.039 Uiso 1 1 calc R . . H15B H 0.1716 0.2278 0.8599 0.039 Uiso 1 1 calc R . . H15C H 0.3325 0.1839 0.8947 0.039 Uiso 1 1 calc R . . C1' C 0.5753(10) 1.1401(5) 0.97293(19) 0.0184(14) Uani 1 1 d . . . O1' O 0.4015(7) 1.1703(4) 0.97824(14) 0.0256(11) Uani 1 1 d . . . O2' O 0.6944(7) 1.1829(3) 0.94229(13) 0.0241(11) Uani 1 1 d . . . C2' C 0.6860(10) 1.0529(5) 0.99806(18) 0.0152(13) Uani 1 1 d . . . C3' C 0.9034(10) 1.0521(5) 0.9794(2) 0.0192(14) Uani 1 1 d . . . H3'A H 1.0043 1.0744 1.0020 0.023 Uiso 1 1 calc R . . C4' C 0.9380(10) 0.9308(5) 0.9663(2) 0.0223(15) Uani 1 1 d . . . H4'A H 1.0805 0.9078 0.9735 0.027 Uiso 1 1 calc R . . O3' O 0.7940(7) 0.8727(3) 0.99244(14) 0.0207(10) Uani 1 1 d . . . C5' C 0.8913(10) 0.9061(5) 0.9193(2) 0.0212(15) Uani 1 1 d . . . O4' O 1.0277(7) 0.8954(4) 0.89280(15) 0.0311(12) Uani 1 1 d . . . C6' C 0.6707(10) 0.9072(5) 0.9083(2) 0.0165(14) Uani 1 1 d . . . C7' C 0.5401(10) 0.9270(4) 0.94060(18) 0.0144(13) Uani 1 1 d . . . H7'A H 0.3993 0.9360 0.9340 0.017 Uiso 1 1 calc R . . C8' C 0.6082(10) 0.9354(5) 0.98750(19) 0.0154(13) Uani 1 1 d . . . C9' C 0.4487(10) 0.8922(5) 1.0178(2) 0.0188(14) Uani 1 1 d . . . H9'A H 0.3942 0.8219 1.0122 0.023 Uiso 1 1 calc R . . C10' C 0.3793(9) 0.9452(5) 1.05176(18) 0.0136(13) Uani 1 1 d . . . C11' C 0.4672(10) 1.0510(5) 1.06544(19) 0.0183(14) Uani 1 1 d . . . H11C H 0.4747 1.0529 1.0974 0.022 Uiso 1 1 calc R . . H11D H 0.3749 1.1103 1.0561 0.022 Uiso 1 1 calc R . . C12' C 0.6792(10) 1.0715(5) 1.04702(18) 0.0160(13) Uani 1 1 d . . . H12C H 0.7782 1.0222 1.0612 0.019 Uiso 1 1 calc R . . H12D H 0.7204 1.1472 1.0534 0.019 Uiso 1 1 calc R . . C13' C 0.8979(11) 1.1369(5) 0.9425(2) 0.0281(17) Uani 1 1 d . . . H13C H 1.0009 1.1945 0.9475 0.034 Uiso 1 1 calc R . . H13D H 0.9276 1.1016 0.9144 0.034 Uiso 1 1 calc R . . C14' C 0.6110(10) 0.8907(5) 0.86225(19) 0.0235(15) Uani 1 1 d . . . H14D H 0.4618 0.8886 0.8600 0.035 Uiso 1 1 calc R . . H14E H 0.6680 0.8218 0.8518 0.035 Uiso 1 1 calc R . . H14F H 0.6642 0.9507 0.8447 0.035 Uiso 1 1 calc R . . C15' C 0.2110(11) 0.8996(5) 1.0793(2) 0.0240(15) Uani 1 1 d . . . H15D H 0.1464 0.8384 1.0643 0.036 Uiso 1 1 calc R . . H15E H 0.1090 0.9562 1.0848 0.036 Uiso 1 1 calc R . . H15F H 0.2680 0.8743 1.1068 0.036 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 0.016(4) 0.019(3) 0.024(4) -0.002(3) -0.004(3) -0.001(3) O1 0.016(3) 0.025(2) 0.029(3) 0.005(2) 0.005(2) 0.005(2) O2 0.022(3) 0.024(2) 0.029(3) 0.011(2) 0.005(2) 0.003(2) C2 0.010(3) 0.012(3) 0.020(3) -0.001(3) 0.001(3) 0.002(3) C3 0.019(3) 0.017(3) 0.019(3) -0.005(3) 0.002(3) -0.007(3) C4 0.012(3) 0.019(3) 0.018(3) 0.006(3) -0.004(3) 0.000(3) O3 0.017(2) 0.012(2) 0.023(2) 0.0003(18) 0.0001(19) 0.0030(19) C5 0.021(3) 0.003(3) 0.024(3) 0.003(2) 0.004(3) 0.003(3) O4 0.018(2) 0.027(3) 0.027(3) -0.008(2) 0.008(2) 0.006(2) C6 0.019(3) 0.010(3) 0.019(3) -0.001(3) 0.004(3) 0.000(3) C7 0.018(3) 0.018(3) 0.018(3) -0.007(3) -0.005(3) -0.003(3) C8 0.015(3) 0.009(3) 0.016(3) 0.002(2) 0.000(3) 0.007(3) C9 0.018(3) 0.013(3) 0.023(3) 0.003(3) -0.003(3) -0.006(3) C10 0.016(3) 0.023(3) 0.011(3) 0.002(3) -0.002(3) 0.001(3) C11 0.032(4) 0.026(4) 0.015(3) 0.001(3) -0.001(3) 0.012(3) C12 0.024(4) 0.009(3) 0.021(3) -0.010(2) 0.001(3) 0.003(3) C13 0.019(3) 0.014(3) 0.031(4) -0.002(3) 0.007(3) 0.000(3) C14 0.023(4) 0.039(4) 0.014(3) -0.003(3) 0.001(3) -0.004(3) C15 0.022(4) 0.035(4) 0.021(3) 0.007(3) -0.004(3) -0.002(3) C1' 0.024(4) 0.018(3) 0.014(3) -0.002(2) 0.001(3) -0.008(3) O1' 0.028(3) 0.029(3) 0.020(2) 0.002(2) -0.001(2) 0.007(2) O2' 0.026(3) 0.027(2) 0.020(2) 0.004(2) 0.002(2) -0.001(2) C2' 0.015(3) 0.018(3) 0.013(3) -0.003(3) -0.002(3) 0.002(3) C3' 0.012(3) 0.023(3) 0.023(3) -0.001(3) -0.006(3) -0.005(3) C4' 0.009(3) 0.028(4) 0.030(4) -0.005(3) -0.001(3) 0.007(3) O3' 0.021(2) 0.018(2) 0.023(2) -0.0009(19) -0.003(2) 0.0091(19) C5' 0.026(4) 0.012(3) 0.025(4) -0.003(3) 0.007(3) 0.004(3) O4' 0.021(3) 0.043(3) 0.029(3) -0.006(2) 0.008(2) 0.003(2) C6' 0.020(3) 0.010(3) 0.020(3) -0.001(3) -0.004(3) 0.001(3) C7' 0.018(3) 0.010(3) 0.015(3) -0.007(2) 0.000(3) 0.000(3) C8' 0.015(3) 0.012(3) 0.019(3) 0.003(3) -0.001(3) 0.007(3) C9' 0.019(3) 0.009(3) 0.029(4) 0.003(3) -0.004(3) -0.004(3) C10' 0.014(3) 0.015(3) 0.012(3) 0.006(2) 0.000(3) 0.005(3) C11' 0.019(3) 0.023(3) 0.013(3) 0.000(3) 0.003(3) 0.006(3) C12' 0.025(4) 0.009(3) 0.014(3) 0.001(2) -0.004(3) -0.002(3) C13' 0.026(4) 0.023(4) 0.035(4) -0.003(3) 0.011(3) 0.000(3) C14' 0.023(4) 0.028(4) 0.019(3) -0.009(3) 0.005(3) 0.007(3) C15' 0.025(4) 0.030(4) 0.018(3) 0.009(3) 0.001(3) 0.001(3) _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 1.206(8) . ? C1 O2 1.337(8) . ? C1 C2 1.503(8) . ? O2 C13 1.467(8) . ? C2 C12 1.537(8) . ? C2 C3 1.538(8) . ? C2 C8 1.570(8) . ? C3 C13 1.527(8) . ? C3 C4 1.558(8) . ? C3 H3A 1.0000 . ? C4 O3 1.434(7) . ? C4 C5 1.510(8) . ? C4 H4A 1.0000 . ? O3 C8 1.446(7) . ? C5 O4 1.213(7) . ? C5 C6 1.489(9) . ? C6 C7 1.333(8) . ? C6 C14 1.488(8) . ? C7 C8 1.515(8) . ? C7 H7A 0.9500 . ? C8 C9 1.490(8) . ? C9 C10 1.319(8) . ? C9 H9A 0.9500 . ? C10 C15 1.504(9) . ? C10 C11 1.506(8) . ? C11 C12 1.509(9) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C1' O1' 1.208(8) . ? C1' O2' 1.337(7) . ? C1' C2' 1.510(9) . ? O2' C13' 1.447(8) . ? C2' C12' 1.534(8) . ? C2' C3' 1.536(9) . ? C2' C8' 1.566(8) . ? C3' C13' 1.549(9) . ? C3' C4' 1.563(9) . ? C3' H3'A 1.0000 . ? C4' O3' 1.433(8) . ? C4' C5' 1.517(9) . ? C4' H4'A 1.0000 . ? O3' C8' 1.448(7) . ? C5' O4' 1.220(8) . ? C5' C6' 1.484(9) . ? C6' C7' 1.339(8) . ? C6' C14' 1.492(8) . ? C7' C8' 1.523(8) . ? C7' H7'A 0.9500 . ? C8' C9' 1.502(9) . ? C9' C10' 1.317(8) . ? C9' H9'A 0.9500 . ? C10' C11' 1.484(8) . ? C10' C15' 1.503(8) . ? C11' C12' 1.521(9) . ? C11' H11C 0.9900 . ? C11' H11D 0.9900 . ? C12' H12C 0.9900 . ? C12' H12D 0.9900 . ? C13' H13C 0.9900 . ? C13' H13D 0.9900 . ? C14' H14D 0.9800 . ? C14' H14E 0.9800 . ? C14' H14F 0.9800 . ? C15' H15D 0.9800 . ? C15' H15E 0.9800 . ? C15' H15F 0.9800 . ? 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 O2 120.7(6) . . ? O1 C1 C2 127.5(6) . . ? O2 C1 C2 111.7(5) . . ? C1 O2 C13 111.8(5) . . ? C1 C2 C12 112.8(5) . . ? C1 C2 C3 104.5(5) . . ? C12 C2 C3 113.7(5) . . ? C1 C2 C8 112.6(5) . . ? C12 C2 C8 110.0(5) . . ? C3 C2 C8 102.7(5) . . ? C13 C3 C2 105.4(5) . . ? C13 C3 C4 116.9(5) . . ? C2 C3 C4 103.4(5) . . ? C13 C3 H3A 110.2 . . ? C2 C3 H3A 110.2 . . ? C4 C3 H3A 110.2 . . ? O3 C4 C5 107.2(5) . . ? O3 C4 C3 104.2(5) . . ? C5 C4 C3 114.3(5) . . ? O3 C4 H4A 110.3 . . ? C5 C4 H4A 110.3 . . ? C3 C4 H4A 110.3 . . ? C4 O3 C8 103.2(4) . . ? O4 C5 C6 122.7(5) . . ? O4 C5 C4 122.8(6) . . ? C6 C5 C4 114.4(5) . . ? C7 C6 C14 124.7(6) . . ? C7 C6 C5 116.5(5) . . ? C14 C6 C5 118.7(5) . . ? C6 C7 C8 122.9(6) . . ? C6 C7 H7A 118.6 . . ? C8 C7 H7A 118.6 . . ? O3 C8 C9 109.6(5) . . ? O3 C8 C7 108.4(5) . . ? C9 C8 C7 112.0(5) . . ? O3 C8 C2 100.9(5) . . ? C9 C8 C2 114.7(5) . . ? C7 C8 C2 110.5(5) . . ? C10 C9 C8 125.3(6) . . ? C10 C9 H9A 117.3 . . ? C8 C9 H9A 117.3 . . ? C9 C10 C15 122.6(6) . . ? C9 C10 C11 120.9(6) . . ? C15 C10 C11 116.4(5) . . ? C10 C11 C12 113.6(5) . . ? C10 C11 H11A 108.8 . . ? C12 C11 H11A 108.8 . . ? C10 C11 H11B 108.8 . . ? C12 C11 H11B 108.8 . . ? H11A C11 H11B 107.7 . . ? C11 C12 C2 112.2(5) . . ? C11 C12 H12A 109.2 . . ? C2 C12 H12A 109.2 . . ? C11 C12 H12B 109.2 . . ? C2 C12 H12B 109.2 . . ? H12A C12 H12B 107.9 . . ? O2 C13 C3 106.3(5) . . ? O2 C13 H13A 110.5 . . ? C3 C13 H13A 110.5 . . ? O2 C13 H13B 110.5 . . ? C3 C13 H13B 110.5 . . ? H13A C13 H13B 108.7 . . ? C6 C14 H14A 109.5 . . ? C6 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C6 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C10 C15 H15A 109.5 . . ? C10 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C10 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? O1' C1' O2' 121.7(6) . . ? O1' C1' C2' 126.9(6) . . ? O2' C1' C2' 111.4(6) . . ? C1' O2' C13' 112.4(5) . . ? C1' C2' C12' 113.0(5) . . ? C1' C2' C3' 104.8(5) . . ? C12' C2' C3' 113.5(5) . . ? C1' C2' C8' 113.0(5) . . ? C12' C2' C8' 109.5(5) . . ? C3' C2' C8' 102.6(5) . . ? C2' C3' C13' 104.6(5) . . ? C2' C3' C4' 103.7(5) . . ? C13' C3' C4' 117.0(5) . . ? C2' C3' H3'A 110.4 . . ? C13' C3' H3'A 110.4 . . ? C4' C3' H3'A 110.4 . . ? O3' C4' C5' 108.1(5) . . ? O3' C4' C3' 103.5(5) . . ? C5' C4' C3' 114.3(5) . . ? O3' C4' H4'A 110.3 . . ? C5' C4' H4'A 110.3 . . ? C3' C4' H4'A 110.3 . . ? C4' O3' C8' 103.1(4) . . ? O4' C5' C6' 123.9(6) . . ? O4' C5' C4' 121.3(6) . . ? C6' C5' C4' 114.6(6) . . ? C7' C6' C5' 116.8(6) . . ? C7' C6' C14' 124.9(6) . . ? C5' C6' C14' 118.3(6) . . ? C6' C7' C8' 122.6(6) . . ? C6' C7' H7'A 118.7 . . ? C8' C7' H7'A 118.7 . . ? O3' C8' C9' 109.2(5) . . ? O3' C8' C7' 108.1(5) . . ? C9' C8' C7' 111.7(5) . . ? O3' C8' C2' 101.3(5) . . ? C9' C8' C2' 114.9(5) . . ? C7' C8' C2' 110.9(5) . . ? C10' C9' C8' 124.3(6) . . ? C10' C9' H9'A 117.8 . . ? C8' C9' H9'A 117.8 . . ? C9' C10' C11' 121.9(6) . . ? C9' C10' C15' 121.4(6) . . ? C11' C10' C15' 116.7(5) . . ? C10' C11' C12' 113.0(5) . . ? C10' C11' H11C 109.0 . . ? C12' C11' H11C 109.0 . . ? C10' C11' H11D 109.0 . . ? C12' C11' H11D 109.0 . . ? H11C C11' H11D 107.8 . . ? C11' C12' C2' 111.9(5) . . ? C11' C12' H12C 109.2 . . ? C2' C12' H12C 109.2 . . ? C11' C12' H12D 109.2 . . ? C2' C12' H12D 109.2 . . ? H12C C12' H12D 107.9 . . ? O2' C13' C3' 106.7(5) . . ? O2' C13' H13C 110.4 . . ? C3' C13' H13C 110.4 . . ? O2' C13' H13D 110.4 . . ? C3' C13' H13D 110.4 . . ? H13C C13' H13D 108.6 . . ? C6' C14' H14D 109.5 . . ? C6' C14' H14E 109.5 . . ? H14D C14' H14E 109.5 . . ? C6' C14' H14F 109.5 . . ? H14D C14' H14F 109.5 . . ? H14E C14' H14F 109.5 . . ? C10' C15' H15D 109.5 . . ? C10' C15' H15E 109.5 . . ? H15D C15' H15E 109.5 . . ? C10' C15' H15F 109.5 . . ? H15D C15' H15F 109.5 . . ? H15E C15' H15F 109.5 . . ? 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 O2 C13 -177.9(6) . . . . ? C2 C1 O2 C13 1.6(7) . . . . ? O1 C1 C2 C12 -55.1(9) . . . . ? O2 C1 C2 C12 125.4(6) . . . . ? O1 C1 C2 C3 -179.1(7) . . . . ? O2 C1 C2 C3 1.5(7) . . . . ? O1 C1 C2 C8 70.1(8) . . . . ? O2 C1 C2 C8 -109.3(6) . . . . ? C1 C2 C3 C13 -3.7(6) . . . . ? C12 C2 C3 C13 -127.1(5) . . . . ? C8 C2 C3 C13 114.0(5) . . . . ? C1 C2 C3 C4 -126.9(5) . . . . ? C12 C2 C3 C4 109.6(5) . . . . ? C8 C2 C3 C4 -9.2(6) . . . . ? C13 C3 C4 O3 -136.2(5) . . . . ? C2 C3 C4 O3 -20.9(6) . . . . ? C13 C3 C4 C5 -19.4(8) . . . . ? C2 C3 C4 C5 95.8(6) . . . . ? C5 C4 O3 C8 -75.9(5) . . . . ? C3 C4 O3 C8 45.6(5) . . . . ? O3 C4 C5 O4 -135.7(6) . . . . ? C3 C4 C5 O4 109.4(7) . . . . ? O3 C4 C5 C6 46.6(6) . . . . ? C3 C4 C5 C6 -68.3(7) . . . . ? O4 C5 C6 C7 175.2(6) . . . . ? C4 C5 C6 C7 -7.0(8) . . . . ? O4 C5 C6 C14 -5.7(9) . . . . ? C4 C5 C6 C14 172.0(5) . . . . ? C14 C6 C7 C8 178.5(6) . . . . ? C5 C6 C7 C8 -2.5(9) . . . . ? C4 O3 C8 C9 -172.3(5) . . . . ? C4 O3 C8 C7 65.1(5) . . . . ? C4 O3 C8 C2 -51.0(5) . . . . ? C6 C7 C8 O3 -27.1(8) . . . . ? C6 C7 C8 C9 -148.2(6) . . . . ? C6 C7 C8 C2 82.6(7) . . . . ? C1 C2 C8 O3 147.9(5) . . . . ? C12 C2 C8 O3 -85.4(6) . . . . ? C3 C2 C8 O3 36.0(5) . . . . ? C1 C2 C8 C9 -94.4(6) . . . . ? C12 C2 C8 C9 32.3(7) . . . . ? C3 C2 C8 C9 153.7(5) . . . . ? C1 C2 C8 C7 33.3(7) . . . . ? C12 C2 C8 C7 160.1(5) . . . . ? C3 C2 C8 C7 -78.6(6) . . . . ? O3 C8 C9 C10 109.0(7) . . . . ? C7 C8 C9 C10 -130.5(6) . . . . ? C2 C8 C9 C10 -3.6(9) . . . . ? C8 C9 C10 C15 172.6(6) . . . . ? C8 C9 C10 C11 -4.1(10) . . . . ? C9 C10 C11 C12 -18.7(8) . . . . ? C15 C10 C11 C12 164.4(5) . . . . ? C10 C11 C12 C2 48.4(7) . . . . ? C1 C2 C12 C11 72.0(6) . . . . ? C3 C2 C12 C11 -169.1(5) . . . . ? C8 C2 C12 C11 -54.6(6) . . . . ? C1 O2 C13 C3 -4.0(7) . . . . ? C2 C3 C13 O2 4.6(6) . . . . ? C4 C3 C13 O2 118.7(6) . . . . ? O1' C1' O2' C13' 178.3(6) . . . . ? C2' C1' O2' C13' -1.9(7) . . . . ? O1' C1' C2' C12' -53.1(9) . . . . ? O2' C1' C2' C12' 127.1(6) . . . . ? O1' C1' C2' C3' -177.2(6) . . . . ? O2' C1' C2' C3' 3.1(7) . . . . ? O1' C1' C2' C8' 71.9(8) . . . . ? O2' C1' C2' C8' -107.8(6) . . . . ? C1' C2' C3' C13' -2.9(6) . . . . ? C12' C2' C3' C13' -126.6(5) . . . . ? C8' C2' C3' C13' 115.3(5) . . . . ? C1' C2' C3' C4' -126.0(5) . . . . ? C12' C2' C3' C4' 110.3(6) . . . . ? C8' C2' C3' C4' -7.8(6) . . . . ? C2' C3' C4' O3' -22.3(6) . . . . ? C13' C3' C4' O3' -136.8(5) . . . . ? C2' C3' C4' C5' 95.0(6) . . . . ? C13' C3' C4' C5' -19.6(8) . . . . ? C5' C4' O3' C8' -75.3(5) . . . . ? C3' C4' O3' C8' 46.2(6) . . . . ? O3' C4' C5' O4' -142.8(6) . . . . ? C3' C4' C5' O4' 102.7(7) . . . . ? O3' C4' C5' C6' 42.9(7) . . . . ? C3' C4' C5' C6' -71.7(7) . . . . ? O4' C5' C6' C7' -175.7(6) . . . . ? C4' C5' C6' C7' -1.5(8) . . . . ? O4' C5' C6' C14' 2.1(10) . . . . ? C4' C5' C6' C14' 176.3(5) . . . . ? C5' C6' C7' C8' -6.7(8) . . . . ? C14' C6' C7' C8' 175.6(6) . . . . ? C4' O3' C8' C9' -172.8(5) . . . . ? C4' O3' C8' C7' 65.5(5) . . . . ? C4' O3' C8' C2' -51.1(5) . . . . ? C6' C7' C8' O3' -25.8(7) . . . . ? C6' C7' C8' C9' -146.0(6) . . . . ? C6' C7' C8' C2' 84.4(7) . . . . ? C1' C2' C8' O3' 147.2(5) . . . . ? C12' C2' C8' O3' -85.9(6) . . . . ? C3' C2' C8' O3' 35.0(5) . . . . ? C1' C2' C8' C9' -95.2(6) . . . . ? C12' C2' C8' C9' 31.7(7) . . . . ? C3' C2' C8' C9' 152.6(5) . . . . ? C1' C2' C8' C7' 32.7(7) . . . . ? C12' C2' C8' C7' 159.6(5) . . . . ? C3' C2' C8' C7' -79.6(6) . . . . ? O3' C8' C9' C10' 111.3(6) . . . . ? C7' C8' C9' C10' -129.2(6) . . . . ? C2' C8' C9' C10' -1.7(9) . . . . ? C8' C9' C10' C11' -5.4(10) . . . . ? C8' C9' C10' C15' 176.5(6) . . . . ? C9' C10' C11' C12' -19.1(8) . . . . ? C15' C10' C11' C12' 159.0(5) . . . . ? C10' C11' C12' C2' 50.1(7) . . . . ? C1' C2' C12' C11' 71.4(7) . . . . ? C3' C2' C12' C11' -169.5(5) . . . . ? C8' C2' C12' C11' -55.5(6) . . . . ? C1' O2' C13' C3' -0.1(7) . . . . ? C2' C3' C13' O2' 2.0(7) . . . . ? C4' C3' C13' O2' 116.0(6) . . . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 25.05 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.286 _refine_diff_density_min -0.260 _refine_diff_density_rms 0.066