# Supplementary Material (ESI) for Perkin Transactions # This journal is © The Royal Society of Chemistry 2002 data_seco2 _database_code_CSD 181809 _journal_coden_Cambridge 207 loop_ _publ_author_name 'Eklund, Patrik Christoffer' 'Sillanpaa, Reijo' 'Sjoholm, Rainer' _publ_contact_author_name 'Mr Patrik Christoffer Eklund' _publ_contact_author_address ; Department of Organic chemistry Abo Akademi Biskopsgatan 8 2500 Abo TURKU 20500 Turku FINLAND ; _publ_contact_author_email 'PAEKLUND@ABO.FI' _publ_requested_journal 'Perkin Transactions 1' _publ_section_title ; Synthetic transformation of Hydroxymatairesinol from Norway spruce (Picea abies) to 7-hydroxy-secoisolariciresinol, (+)-lariciresinol and (+)-cyclolariciresinol. ; _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C20 H26 O7, C1 H4 O1' ? _chemical_formula_sum 'C21 H30 O8' _chemical_formula_weight 410.45 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 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+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' _cell_length_a 8.9956(2) _cell_length_b 12.2107(2) _cell_length_c 18.5397(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2036.45(8) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 6675 _cell_measurement_theta_max 25.028 _cell_measurement_theta_min 1.018 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.339 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 880 _exptl_absorpt_coefficient_mu 0.102 _exptl_absorpt_correction_type no _exptl_absorpt_correction_T_min 0.9759 _exptl_absorpt_correction_T_max 0.9858 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator 'horizonally mounted graphite crystal' _diffrn_radiation_probe x-ray _diffrn_radiation_wavelength 0.71073 _diffrn_source 'Enraf Nonius FR590' _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 9 _diffrn_measurement_device '95mm CCD camera on \k-goniostat' _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method 'CCD rotation images, thick slices' _diffrn_standards_decay_% 0 _diffrn_reflns_number 12147 _diffrn_reflns_av_R_equivalents 0.0413 _diffrn_reflns_av_sigmaI/netI 0.0377 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 2.00 _diffrn_reflns_theta_max 25.03 _reflns_number_total 3585 _reflns_number_gt 3192 _reflns_threshold_expression >2\s(I) _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack (Otwinowski & Minor 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _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^)+(0.0504P)^2^+0.6598P] 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 0.6(10) _refine_ls_number_reflns 3585 _refine_ls_number_parameters 287 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0492 _refine_ls_R_factor_gt 0.0400 _refine_ls_wR_factor_ref 0.0998 _refine_ls_wR_factor_gt 0.0949 _refine_ls_goodness_of_fit_ref 1.091 _refine_ls_restrained_S_all 1.094 _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 O3' O 0.88798(18) 0.54497(12) -0.05201(9) 0.0211(4) Uani 1 1 d . . . O4' O 0.74300(19) 0.70149(14) -0.11779(9) 0.0201(4) Uani 1 1 d . . . H4' H 0.707(3) 0.761(3) -0.1291(16) 0.034(9) Uiso 1 1 d . . . O9' O 0.72371(18) 0.47674(14) 0.29346(9) 0.0216(4) Uani 1 1 d . . . H9' H 0.734(3) 0.430(2) 0.3269(15) 0.022(7) Uiso 1 1 d . . . O3 O 0.49457(19) 0.50423(13) -0.12527(9) 0.0258(4) Uani 1 1 d . . . O4 O 0.7027(2) 0.34582(14) -0.12235(11) 0.0256(4) Uani 1 1 d . . . H4 H 0.708(4) 0.396(3) -0.153(2) 0.053(11) Uiso 1 1 d . . . O7 O 0.3571(2) 0.34305(16) 0.18078(11) 0.0403(5) Uani 1 1 d D . . H7 H 0.319(4) 0.282(2) 0.1610(17) 0.048 Uiso 1 1 d D . . O9 O 0.1584(2) 0.61249(14) 0.18072(10) 0.0261(4) Uani 1 1 d . . . H9 H 0.092(4) 0.561(3) 0.1881(18) 0.045(9) Uiso 1 1 d . . . O10 O -0.0426(2) 0.44787(14) 0.19935(11) 0.0298(4) Uani 1 1 d . . . H10 H -0.114(4) 0.459(2) 0.2292(17) 0.036(8) Uiso 1 1 d . . . C1' C 0.6780(2) 0.65971(17) 0.10344(13) 0.0161(5) Uani 1 1 d . . . C2' C 0.7746(2) 0.59130(18) 0.06429(12) 0.0166(5) Uani 1 1 d . . . H2' H 0.8257 0.5338 0.0884 0.020 Uiso 1 1 calc R . . C3' C 0.7958(2) 0.60685(17) -0.00877(13) 0.0161(5) Uani 1 1 d . . . C4' C 0.7206(3) 0.69183(18) -0.04495(12) 0.0161(5) Uani 1 1 d . . . C5' C 0.6275(3) 0.75974(18) -0.00644(13) 0.0178(5) Uani 1 1 d . . . H5' H 0.5775 0.8179 -0.0303 0.021 Uiso 1 1 calc R . . C6' C 0.6061(3) 0.74367(17) 0.06750(13) 0.0176(5) Uani 1 1 d . . . H6' H 0.5414 0.7910 0.0934 0.021 Uiso 1 1 calc R . . C7' C 0.6495(3) 0.63748(18) 0.18252(13) 0.0186(5) Uani 1 1 d . . . H7'1 H 0.5901 0.6982 0.2030 0.022 Uiso 1 1 calc R . . H7'2 H 0.7456 0.6349 0.2085 0.022 Uiso 1 1 calc R . . C8' C 0.5654(2) 0.52766(18) 0.19434(12) 0.0162(5) Uani 1 1 d . . . H8' H 0.6195 0.4703 0.1661 0.019 Uiso 1 1 calc R . . C9' C 0.5702(3) 0.4930(2) 0.27311(13) 0.0206(5) Uani 1 1 d . . . H9'1 H 0.5247 0.5503 0.3037 0.025 Uiso 1 1 calc R . . H9'2 H 0.5136 0.4242 0.2798 0.025 Uiso 1 1 calc R . . C1 C 0.4434(3) 0.40050(18) 0.06113(13) 0.0186(5) Uani 1 1 d . . . C2 C 0.4220(3) 0.46399(19) -0.00103(13) 0.0196(5) Uani 1 1 d . . . H2 H 0.3486 0.5199 -0.0011 0.024 Uiso 1 1 calc R . . C3 C 0.5062(3) 0.44607(18) -0.06186(13) 0.0184(5) Uani 1 1 d . . . C4 C 0.6156(3) 0.36388(18) -0.06217(13) 0.0207(5) Uani 1 1 d . . . C5 C 0.6347(3) 0.29919(18) -0.00168(15) 0.0243(6) Uani 1 1 d . . . H5 H 0.7064 0.2421 -0.0021 0.029 Uiso 1 1 calc R . . C6 C 0.5495(3) 0.31727(18) 0.05961(14) 0.0224(5) Uani 1 1 d . . . H6 H 0.5637 0.2725 0.1009 0.027 Uiso 1 1 calc R . . C7 C 0.3544(3) 0.42703(18) 0.12823(13) 0.0193(5) Uani 1 1 d . . . H70 H 0.2485 0.4372 0.1131 0.023 Uiso 1 1 calc R . . C8 C 0.4060(3) 0.53481(18) 0.16295(12) 0.0167(5) Uani 1 1 d . . . H8 H 0.4103 0.5899 0.1231 0.020 Uiso 1 1 calc R . . C9 C 0.2912(3) 0.5778(2) 0.21708(13) 0.0208(5) Uani 1 1 d . . . H91 H 0.2665 0.5194 0.2521 0.026(7) Uiso 1 1 calc R . . H92 H 0.3339 0.6402 0.2441 0.013(6) Uiso 1 1 calc R . . C11 C 0.9708(3) 0.4605(2) -0.01759(14) 0.0242(6) Uani 1 1 d . . . H11A H 0.9022 0.4075 0.0041 0.036 Uiso 1 1 calc R . . H11B H 1.0336 0.4924 0.0201 0.036 Uiso 1 1 calc R . . H11C H 1.0334 0.4234 -0.0533 0.036 Uiso 1 1 calc R . . C10 C 0.3875(3) 0.5904(2) -0.12676(14) 0.0263(6) Uani 1 1 d . . . H10A H 0.4097 0.6431 -0.0884 0.039 Uiso 1 1 calc R . . H10B H 0.2880 0.5598 -0.1193 0.039 Uiso 1 1 calc R . . H10C H 0.3913 0.6273 -0.1736 0.039 Uiso 1 1 calc R . . C12 C -0.0563(4) 0.3365(2) 0.17741(19) 0.0429(8) Uani 1 1 d . . . H12A H 0.0250 0.3180 0.1444 0.064 Uiso 1 1 calc R . . H12B H -0.1517 0.3260 0.1529 0.064 Uiso 1 1 calc R . . H12C H -0.0516 0.2889 0.2199 0.064 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 O3' 0.0231(9) 0.0184(8) 0.0216(9) 0.0001(7) 0.0050(7) 0.0072(7) O4' 0.0270(9) 0.0182(8) 0.0150(9) 0.0027(7) 0.0014(7) 0.0051(7) O9' 0.0211(9) 0.0238(9) 0.0198(9) 0.0060(8) -0.0041(7) 0.0008(7) O3 0.0271(9) 0.0298(10) 0.0204(10) 0.0044(7) 0.0063(8) 0.0075(7) O4 0.0296(10) 0.0196(8) 0.0276(10) -0.0008(8) 0.0106(8) 0.0028(7) O7 0.0548(13) 0.0319(10) 0.0343(12) 0.0041(9) 0.0002(10) -0.0134(10) O9 0.0191(9) 0.0258(9) 0.0334(11) 0.0098(8) -0.0014(8) -0.0003(8) O10 0.0252(10) 0.0291(10) 0.0351(12) 0.0003(8) 0.0070(9) -0.0011(8) C1' 0.0150(11) 0.0166(11) 0.0168(13) -0.0012(9) -0.0006(9) -0.0059(9) C2' 0.0169(11) 0.0143(10) 0.0185(13) 0.0030(9) -0.0016(10) -0.0002(9) C3' 0.0125(11) 0.0131(10) 0.0227(13) 0.0006(9) 0.0026(10) -0.0009(9) C4' 0.0175(11) 0.0172(10) 0.0135(12) 0.0016(9) 0.0002(9) -0.0021(9) C5' 0.0181(12) 0.0154(11) 0.0198(13) 0.0036(9) -0.0009(10) 0.0027(9) C6' 0.0181(12) 0.0122(10) 0.0226(14) -0.0011(9) 0.0008(10) -0.0005(9) C7' 0.0209(12) 0.0191(11) 0.0158(12) -0.0022(9) -0.0005(10) -0.0023(9) C8' 0.0164(11) 0.0166(10) 0.0157(12) 0.0006(9) 0.0014(9) -0.0006(9) C9' 0.0169(12) 0.0265(12) 0.0183(13) 0.0039(10) -0.0023(10) -0.0012(10) C1 0.0182(11) 0.0181(11) 0.0196(13) -0.0047(10) -0.0028(10) -0.0081(9) C2 0.0166(11) 0.0217(11) 0.0205(13) -0.0039(10) -0.0023(10) -0.0005(9) C3 0.0185(12) 0.0195(11) 0.0173(12) -0.0020(10) -0.0025(10) -0.0033(9) C4 0.0208(12) 0.0193(11) 0.0221(14) -0.0064(10) 0.0019(11) -0.0036(9) C5 0.0258(13) 0.0154(11) 0.0317(15) -0.0002(10) -0.0002(11) 0.0006(10) C6 0.0283(13) 0.0157(11) 0.0230(14) 0.0017(10) -0.0015(12) -0.0033(10) C7 0.0188(12) 0.0234(12) 0.0158(12) 0.0022(9) 0.0021(10) -0.0068(9) C8 0.0181(12) 0.0187(11) 0.0132(12) 0.0025(10) 0.0003(9) -0.0028(9) C9 0.0178(12) 0.0242(12) 0.0203(13) 0.0060(10) -0.0015(10) 0.0006(10) C11 0.0231(13) 0.0192(12) 0.0303(14) 0.0021(11) 0.0002(11) 0.0085(10) C10 0.0254(13) 0.0306(13) 0.0228(14) 0.0037(11) 0.0014(11) 0.0090(11) C12 0.0448(18) 0.0376(16) 0.047(2) -0.0054(14) 0.0042(15) 0.0045(14) _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 O3' C3' 1.379(3) . ? O3' C11 1.423(3) . ? O4' C4' 1.371(3) . ? O4' H4' 0.82(3) . ? O9' C9' 1.445(3) . ? O9' H9' 0.85(3) . ? O3 C3 1.378(3) . ? O3 C10 1.426(3) . ? O4 C4 1.381(3) . ? O4 H4 0.84(4) . ? O7 C7 1.415(3) . ? O7 H7 0.894(18) . ? O9 C9 1.436(3) . ? O9 H9 0.88(4) . ? O10 C12 1.425(3) . ? O10 H10 0.86(3) . ? C1' C6' 1.383(3) . ? C1' C2' 1.407(3) . ? C1' C7' 1.513(3) . ? C2' C3' 1.381(3) . ? C2' H2' 0.9500 . ? C3' C4' 1.409(3) . ? C4' C5' 1.378(3) . ? C5' C6' 1.398(3) . ? C5' H5' 0.9500 . ? C6' H6' 0.9500 . ? C7' C8' 1.555(3) . ? C7' H7'1 0.9900 . ? C7' H7'2 0.9900 . ? C8' C9' 1.521(3) . ? C8' C8 1.550(3) . ? C8' H8' 1.0000 . ? C9' H9'1 0.9900 . ? C9' H9'2 0.9900 . ? C1 C6 1.394(3) . ? C1 C2 1.402(3) . ? C1 C7 1.515(3) . ? C2 C3 1.376(3) . ? C2 H2 0.9500 . ? C3 C4 1.406(3) . ? C4 C5 1.382(4) . ? C5 C6 1.388(4) . ? C5 H5 0.9500 . ? C6 H6 0.9500 . ? C7 C8 1.537(3) . ? C7 H70 1.0000 . ? C8 C9 1.533(3) . ? C8 H8 1.0000 . ? C9 H91 0.9900 . ? C9 H92 0.9900 . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 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 C3' O3' C11 116.81(18) . . ? C4' O4' H4' 106(2) . . ? C9' O9' H9' 112.7(18) . . ? C3 O3 C10 116.61(18) . . ? C4 O4 H4 118(2) . . ? C7 O7 H7 108(2) . . ? C9 O9 H9 106(2) . . ? C12 O10 H10 105(2) . . ? C6' C1' C2' 118.7(2) . . ? C6' C1' C7' 121.4(2) . . ? C2' C1' C7' 119.9(2) . . ? C3' C2' C1' 120.6(2) . . ? C3' C2' H2' 119.7 . . ? C1' C2' H2' 119.7 . . ? O3' C3' C2' 125.31(19) . . ? O3' C3' C4' 114.6(2) . . ? C2' C3' C4' 120.1(2) . . ? O4' C4' C5' 123.2(2) . . ? O4' C4' C3' 117.5(2) . . ? C5' C4' C3' 119.2(2) . . ? C4' C5' C6' 120.5(2) . . ? C4' C5' H5' 119.8 . . ? C6' C5' H5' 119.8 . . ? C1' C6' C5' 120.8(2) . . ? C1' C6' H6' 119.6 . . ? C5' C6' H6' 119.6 . . ? C1' C7' C8' 111.93(18) . . ? C1' C7' H7'1 109.2 . . ? C8' C7' H7'1 109.2 . . ? C1' C7' H7'2 109.2 . . ? C8' C7' H7'2 109.2 . . ? H7'1 C7' H7'2 107.9 . . ? C9' C8' C8 113.73(19) . . ? C9' C8' C7' 111.20(18) . . ? C8 C8' C7' 110.40(18) . . ? C9' C8' H8' 107.0 . . ? C8 C8' H8' 107.0 . . ? C7' C8' H8' 107.0 . . ? O9' C9' C8' 108.42(19) . . ? O9' C9' H9'1 110.0 . . ? C8' C9' H9'1 110.0 . . ? O9' C9' H9'2 110.0 . . ? C8' C9' H9'2 110.0 . . ? H9'1 C9' H9'2 108.4 . . ? C6 C1 C2 118.7(2) . . ? C6 C1 C7 122.3(2) . . ? C2 C1 C7 118.9(2) . . ? C3 C2 C1 120.7(2) . . ? C3 C2 H2 119.7 . . ? C1 C2 H2 119.7 . . ? C2 C3 O3 125.2(2) . . ? C2 C3 C4 120.2(2) . . ? O3 C3 C4 114.7(2) . . ? O4 C4 C5 119.6(2) . . ? O4 C4 C3 121.0(2) . . ? C5 C4 C3 119.4(2) . . ? C4 C5 C6 120.3(2) . . ? C4 C5 H5 119.8 . . ? C6 C5 H5 119.8 . . ? C5 C6 C1 120.7(2) . . ? C5 C6 H6 119.7 . . ? C1 C6 H6 119.7 . . ? O7 C7 C1 113.7(2) . . ? O7 C7 C8 109.09(19) . . ? C1 C7 C8 111.54(18) . . ? O7 C7 H70 107.4 . . ? C1 C7 H70 107.4 . . ? C8 C7 H70 107.4 . . ? C9 C8 C7 111.34(19) . . ? C9 C8 C8' 113.38(19) . . ? C7 C8 C8' 112.88(19) . . ? C9 C8 H8 106.2 . . ? C7 C8 H8 106.2 . . ? C8' C8 H8 106.2 . . ? O9 C9 C8 110.75(19) . . ? O9 C9 H91 109.5 . . ? C8 C9 H91 109.5 . . ? O9 C9 H92 109.5 . . ? C8 C9 H92 109.5 . . ? H91 C9 H92 108.1 . . ? O3' C11 H11A 109.5 . . ? O3' C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? O3' C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? O3 C10 H10A 109.5 . . ? O3 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? O3 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? O10 C12 H12A 109.5 . . ? O10 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? O10 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 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 C6' C1' C2' C3' -0.8(3) . . . . ? C7' C1' C2' C3' 176.6(2) . . . . ? C11 O3' C3' C2' -2.0(3) . . . . ? C11 O3' C3' C4' 177.79(19) . . . . ? C1' C2' C3' O3' 179.8(2) . . . . ? C1' C2' C3' C4' 0.0(3) . . . . ? O3' C3' C4' O4' 1.9(3) . . . . ? C2' C3' C4' O4' -178.3(2) . . . . ? O3' C3' C4' C5' -178.9(2) . . . . ? C2' C3' C4' C5' 0.8(3) . . . . ? O4' C4' C5' C6' 178.2(2) . . . . ? C3' C4' C5' C6' -0.9(3) . . . . ? C2' C1' C6' C5' 0.7(3) . . . . ? C7' C1' C6' C5' -176.6(2) . . . . ? C4' C5' C6' C1' 0.1(3) . . . . ? C6' C1' C7' C8' 111.1(2) . . . . ? C2' C1' C7' C8' -66.2(3) . . . . ? C1' C7' C8' C9' 166.35(19) . . . . ? C1' C7' C8' C8 -66.4(2) . . . . ? C8 C8' C9' O9' 173.28(18) . . . . ? C7' C8' C9' O9' -61.3(2) . . . . ? C6 C1 C2 C3 -1.4(3) . . . . ? C7 C1 C2 C3 176.6(2) . . . . ? C1 C2 C3 O3 -179.5(2) . . . . ? C1 C2 C3 C4 -0.3(3) . . . . ? C10 O3 C3 C2 0.8(3) . . . . ? C10 O3 C3 C4 -178.4(2) . . . . ? C2 C3 C4 O4 -179.0(2) . . . . ? O3 C3 C4 O4 0.3(3) . . . . ? C2 C3 C4 C5 1.9(3) . . . . ? O3 C3 C4 C5 -178.8(2) . . . . ? O4 C4 C5 C6 179.1(2) . . . . ? C3 C4 C5 C6 -1.9(3) . . . . ? C4 C5 C6 C1 0.2(4) . . . . ? C2 C1 C6 C5 1.5(3) . . . . ? C7 C1 C6 C5 -176.5(2) . . . . ? C6 C1 C7 O7 -16.9(3) . . . . ? C2 C1 C7 O7 165.18(19) . . . . ? C6 C1 C7 C8 107.0(2) . . . . ? C2 C1 C7 C8 -71.0(3) . . . . ? O7 C7 C8 C9 -69.4(2) . . . . ? C1 C7 C8 C9 164.23(19) . . . . ? O7 C7 C8 C8' 59.5(3) . . . . ? C1 C7 C8 C8' -66.9(2) . . . . ? C9' C8' C8 C9 36.7(3) . . . . ? C7' C8' C8 C9 -89.1(2) . . . . ? C9' C8' C8 C7 -91.1(2) . . . . ? C7' C8' C8 C7 143.13(19) . . . . ? C7 C8 C9 O9 -68.1(2) . . . . ? C8' C8 C9 O9 163.30(18) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O4' H4' O9 0.82(3) 1.87(3) 2.665(2) 162(3) 3_565 O9' H9' O4' 0.85(3) 1.92(3) 2.745(2) 165(3) 2_665 O9' H9' O3' 0.85(3) 2.52(3) 3.048(2) 122(2) 2_665 O4 H4 O9' 0.84(4) 1.95(4) 2.751(2) 161(4) 2_664 O7 H7 O4 0.894(18) 2.016(19) 2.902(3) 171(3) 3_455 O9 H9 O10 0.88(4) 1.84(4) 2.725(3) 177(3) . O10 H10 O9' 0.86(3) 1.90(3) 2.755(3) 177(3) 1_455 _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.03 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.733 _refine_diff_density_min -0.256 _refine_diff_density_rms 0.049