# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2011 data_global _journal_coden_Cambridge 182 _journal_volume ? _journal_page_first ? _journal_year ? loop_ _publ_author_name 'Tian, Wei-Sheng' _publ_contact_author_name 'Prof. Wei-Sheng Tian' _publ_contact_author_email wstian@mail.sioc.ac.cn _publ_section_title ; Total syntheses of (Sp)-(+)- and (Rp)-(-)-spiniferin-1, a pair of unusual natural products with planar chirality ; # Attachment '- 5.cif' data_cd24234 _database_code_depnum_ccdc_archive 'CCDC 838548' #TrackingRef '- 5.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C21 H27 N O3' _chemical_formula_weight 341.44 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' N N 0.0061 0.0033 '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 P2(1)2(1)2(1) 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 11.4805(10) _cell_length_b 11.8426(10) _cell_length_c 14.1986(12) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1930.4(3) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 1066 _cell_measurement_theta_min 4.479 _cell_measurement_theta_max 37.914 _exptl_crystal_description ? _exptl_crystal_colour colorless _exptl_crystal_size_max 0.250 _exptl_crystal_size_mid 0.232 _exptl_crystal_size_min 0.196 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.171 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 732 _exptl_absorpt_coefficient_mu 0.078 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.75955 _exptl_absorpt_correction_T_max 1.00000 _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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11865 _diffrn_reflns_av_R_equivalents 0.0775 _diffrn_reflns_av_sigmaI/netI 0.1396 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.24 _diffrn_reflns_theta_max 28.26 _reflns_number_total 4489 _reflns_number_gt 1911 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0226P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0046(6) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 1.1(15) _refine_ls_number_reflns 4489 _refine_ls_number_parameters 266 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.1130 _refine_ls_R_factor_gt 0.0454 _refine_ls_wR_factor_ref 0.0856 _refine_ls_wR_factor_gt 0.0734 _refine_ls_goodness_of_fit_ref 0.701 _refine_ls_restrained_S_all 0.702 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N1 N 0.20681(17) 1.06757(16) 0.19403(13) 0.0465(5) Uani 1 1 d . . . H27 H 0.2105 1.0392 0.2497 0.056 Uiso 1 1 calc R . . O1 O 0.1448(2) 0.64550(19) 0.08309(15) 0.1050(8) Uani 1 1 d . . . O2 O 0.21790(17) 0.94311(16) 0.35583(12) 0.0571(5) Uani 1 1 d D . . O3 O 0.27321(14) 1.06526(14) 0.04709(11) 0.0567(5) Uani 1 1 d . . . C1 C 0.2355(3) 0.7564(2) 0.1993(2) 0.0568(8) Uani 1 1 d . . . C2 C 0.2066(3) 0.7275(3) 0.1014(2) 0.0680(9) Uani 1 1 d . . . C3 C 0.2527(3) 0.8042(3) 0.0279(2) 0.0683(10) Uani 1 1 d . . . C4 C 0.3670(2) 0.8558(2) 0.05872(17) 0.0555(7) Uani 1 1 d . . . H4 H 0.3957 0.9054 0.0095 0.067 Uiso 1 1 calc R . . H5 H 0.4239 0.7963 0.0679 0.067 Uiso 1 1 calc R . . C5 C 0.3536(2) 0.9232(2) 0.15060(15) 0.0405(6) Uani 1 1 d . . . C6 C 0.4759(2) 0.9697(2) 0.18584(19) 0.0511(7) Uani 1 1 d . . . C7 C 0.4650(2) 1.0094(2) 0.28832(19) 0.0610(8) Uani 1 1 d . . . H7 H 0.5396 1.0392 0.3087 0.073 Uiso 1 1 calc R . . H6 H 0.4089 1.0706 0.2910 0.073 Uiso 1 1 calc R . . C8 C 0.4277(2) 0.9181(2) 0.35609(17) 0.0619(8) Uani 1 1 d . . . H9 H 0.4857 0.8585 0.3566 0.074 Uiso 1 1 calc R . . H8 H 0.4229 0.9493 0.4191 0.074 Uiso 1 1 calc R . . C9 C 0.3118(2) 0.8693(2) 0.32935(17) 0.0485(7) Uani 1 1 d D . . C10 C 0.2978(2) 0.8462(2) 0.22462(17) 0.0413(6) Uani 1 1 d . . . C11 C 0.5182(2) 1.0681(2) 0.12518(19) 0.0738(9) Uani 1 1 d . . . H13 H 0.5962 1.0881 0.1432 0.111 Uiso 1 1 calc R . . H12 H 0.4678 1.1319 0.1341 0.111 Uiso 1 1 calc R . . H11 H 0.5173 1.0463 0.0601 0.111 Uiso 1 1 calc R . . C12 C 0.5679(2) 0.8765(2) 0.1811(2) 0.0779(10) Uani 1 1 d . . . H14 H 0.5872 0.8616 0.1165 0.117 Uiso 1 1 calc R . . H15 H 0.5378 0.8090 0.2096 0.117 Uiso 1 1 calc R . . H16 H 0.6365 0.9003 0.2143 0.117 Uiso 1 1 calc R . . C13 C 0.2737(2) 1.0251(2) 0.12652(17) 0.0419(6) Uani 1 1 d . . . C14 C 0.1271(2) 1.1613(2) 0.17616(18) 0.0478(7) Uani 1 1 d . . . C15 C 0.0974(3) 1.2160(2) 0.2703(2) 0.0811(10) Uani 1 1 d . . . H20 H 0.0595 1.1617 0.3101 0.122 Uiso 1 1 calc R . . H18 H 0.0464 1.2790 0.2600 0.122 Uiso 1 1 calc R . . H19 H 0.1676 1.2417 0.3001 0.122 Uiso 1 1 calc R . . C16 C 0.0214(2) 1.1257(2) 0.12292(18) 0.0430(6) Uani 1 1 d . . . C17 C -0.0408(3) 1.2034(3) 0.0711(2) 0.0549(8) Uani 1 1 d . . . C18 C -0.1390(3) 1.1738(3) 0.0224(2) 0.0659(9) Uani 1 1 d . . . C19 C -0.1781(3) 1.0675(4) 0.0231(2) 0.0776(10) Uani 1 1 d . . . C20 C -0.1180(3) 0.9876(3) 0.0742(3) 0.0936(12) Uani 1 1 d . . . H24 H -0.1444 0.9133 0.0754 0.112 Uiso 1 1 calc R . . C21 C -0.0188(3) 1.0169(2) 0.1237(2) 0.0732(9) Uani 1 1 d . . . H25 H 0.0210 0.9622 0.1578 0.088 Uiso 1 1 calc R . . H1 H 0.1992(18) 0.7117(17) 0.2486(15) 0.048(7) Uiso 1 1 d . . . H2 H 0.259(2) 0.765(2) -0.0310(19) 0.080(10) Uiso 1 1 d . . . H3 H 0.193(2) 0.864(2) 0.0188(18) 0.077(10) Uiso 1 1 d . . . H10 H 0.2968(19) 0.7977(14) 0.3639(13) 0.053(7) Uiso 1 1 d D . . H17 H 0.1704(18) 1.2134(17) 0.1389(15) 0.045(7) Uiso 1 1 d . . . H21 H -0.0159(17) 1.2793(16) 0.0681(15) 0.039(7) Uiso 1 1 d . . . H22 H -0.183(2) 1.228(2) -0.010(2) 0.092(11) Uiso 1 1 d . . . H23 H -0.245(2) 1.0442(19) -0.0124(16) 0.065(9) Uiso 1 1 d . . . H26 H 0.209(2) 0.948(2) 0.4148(12) 0.096(11) Uiso 1 1 d 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 N1 0.0519(14) 0.0604(13) 0.0271(11) 0.0045(11) 0.0037(10) 0.0152(12) O1 0.1106(18) 0.1049(18) 0.0995(19) -0.0405(16) 0.0106(16) -0.0404(16) O2 0.0696(13) 0.0722(13) 0.0293(11) 0.0032(10) 0.0075(10) 0.0184(11) O3 0.0720(12) 0.0703(12) 0.0280(9) 0.0082(10) 0.0031(10) 0.0095(11) C1 0.069(2) 0.0499(17) 0.0517(19) -0.0004(16) 0.0130(17) -0.0022(16) C2 0.065(2) 0.066(2) 0.073(2) -0.0227(19) 0.0018(18) -0.0099(18) C3 0.084(3) 0.075(2) 0.046(2) -0.0196(19) 0.0002(19) -0.004(2) C4 0.0669(19) 0.0584(17) 0.0412(16) -0.0050(15) 0.0175(15) 0.0076(16) C5 0.0435(15) 0.0454(15) 0.0326(14) -0.0050(13) 0.0039(12) 0.0058(13) C6 0.0440(16) 0.0555(17) 0.0539(18) 0.0024(15) 0.0027(14) 0.0050(14) C7 0.0527(18) 0.074(2) 0.057(2) -0.0054(17) -0.0121(15) -0.0011(15) C8 0.071(2) 0.075(2) 0.0391(17) -0.0005(17) -0.0140(15) 0.0101(17) C9 0.0589(19) 0.0534(18) 0.0334(16) 0.0082(14) 0.0031(13) 0.0064(16) C10 0.0448(15) 0.0437(15) 0.0355(14) 0.0018(13) 0.0012(13) 0.0041(14) C11 0.0563(18) 0.083(2) 0.082(2) 0.012(2) 0.0036(17) -0.0155(17) C12 0.0523(19) 0.100(2) 0.082(2) -0.003(2) -0.0004(16) 0.0229(17) C13 0.0446(15) 0.0530(17) 0.0279(13) 0.0009(13) -0.0029(13) -0.0052(13) C14 0.0520(18) 0.0463(17) 0.0451(18) 0.0022(14) 0.0021(15) 0.0087(15) C15 0.082(2) 0.089(2) 0.072(2) -0.032(2) -0.0084(18) 0.031(2) C16 0.0447(16) 0.0459(15) 0.0385(15) 0.0047(14) 0.0092(13) 0.0068(14) C17 0.064(2) 0.0514(18) 0.0495(19) -0.0014(16) -0.0035(16) 0.0194(18) C18 0.064(2) 0.083(3) 0.050(2) 0.0024(19) 0.0003(18) 0.026(2) C19 0.046(2) 0.114(3) 0.072(3) -0.008(3) -0.0051(17) -0.002(2) C20 0.074(3) 0.083(2) 0.123(3) 0.017(2) -0.013(2) -0.024(2) C21 0.064(2) 0.068(2) 0.088(3) 0.023(2) -0.0146(19) -0.0052(18) _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 N1 C13 1.327(3) . ? N1 C14 1.461(3) . ? N1 H27 0.8600 . ? O1 C2 1.230(3) . ? O2 C9 1.437(3) . ? O2 H26 0.845(17) . ? O3 C13 1.224(2) . ? C1 C10 1.331(3) . ? C1 C2 1.470(4) . ? C1 H1 0.97(2) . ? C2 C3 1.482(4) . ? C3 C4 1.512(4) . ? C3 H2 0.96(3) . ? C3 H3 0.99(3) . ? C4 C5 1.537(3) . ? C4 H4 0.9700 . ? C4 H5 0.9700 . ? C5 C10 1.531(3) . ? C5 C13 1.554(3) . ? C5 C6 1.590(3) . ? C6 C11 1.529(3) . ? C6 C12 1.529(3) . ? C6 C7 1.534(3) . ? C7 C8 1.510(3) . ? C7 H7 0.9700 . ? C7 H6 0.9700 . ? C8 C9 1.499(3) . ? C8 H9 0.9700 . ? C8 H8 0.9700 . ? C9 C10 1.520(3) . ? C9 H10 0.995(15) . ? C11 H13 0.9600 . ? C11 H12 0.9600 . ? C11 H11 0.9600 . ? C12 H14 0.9600 . ? C12 H15 0.9600 . ? C12 H16 0.9600 . ? C14 C16 1.490(3) . ? C14 C15 1.524(3) . ? C14 H17 0.95(2) . ? C15 H20 0.9600 . ? C15 H18 0.9600 . ? C15 H19 0.9600 . ? C16 C21 1.369(3) . ? C16 C17 1.377(3) . ? C17 C18 1.368(4) . ? C17 H21 0.944(18) . ? C18 C19 1.337(5) . ? C18 H22 0.94(3) . ? C19 C20 1.377(4) . ? C19 H23 0.96(2) . ? C20 C21 1.383(4) . ? C20 H24 0.9300 . ? C21 H25 0.9300 . ? 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 C13 N1 C14 121.7(2) . . ? C13 N1 H27 119.2 . . ? C14 N1 H27 119.2 . . ? C9 O2 H26 113(2) . . ? C10 C1 C2 124.2(3) . . ? C10 C1 H1 118.1(13) . . ? C2 C1 H1 117.3(13) . . ? O1 C2 C1 120.9(3) . . ? O1 C2 C3 122.8(3) . . ? C1 C2 C3 116.3(3) . . ? C2 C3 C4 110.7(3) . . ? C2 C3 H2 110.0(15) . . ? C4 C3 H2 112.6(16) . . ? C2 C3 H3 106.4(15) . . ? C4 C3 H3 110.4(15) . . ? H2 C3 H3 106(2) . . ? C3 C4 C5 111.6(2) . . ? C3 C4 H4 109.3 . . ? C5 C4 H4 109.3 . . ? C3 C4 H5 109.3 . . ? C5 C4 H5 109.3 . . ? H4 C4 H5 108.0 . . ? C10 C5 C4 108.36(19) . . ? C10 C5 C13 111.51(19) . . ? C4 C5 C13 106.01(18) . . ? C10 C5 C6 111.1(2) . . ? C4 C5 C6 111.00(19) . . ? C13 C5 C6 108.78(19) . . ? C11 C6 C12 107.8(2) . . ? C11 C6 C7 109.1(2) . . ? C12 C6 C7 108.6(2) . . ? C11 C6 C5 111.6(2) . . ? C12 C6 C5 110.3(2) . . ? C7 C6 C5 109.4(2) . . ? C8 C7 C6 114.1(2) . . ? C8 C7 H7 108.7 . . ? C6 C7 H7 108.7 . . ? C8 C7 H6 108.7 . . ? C6 C7 H6 108.7 . . ? H7 C7 H6 107.6 . . ? C9 C8 C7 111.5(2) . . ? C9 C8 H9 109.3 . . ? C7 C8 H9 109.3 . . ? C9 C8 H8 109.3 . . ? C7 C8 H8 109.3 . . ? H9 C8 H8 108.0 . . ? O2 C9 C8 111.4(2) . . ? O2 C9 C10 106.6(2) . . ? C8 C9 C10 114.2(2) . . ? O2 C9 H10 105.0(13) . . ? C8 C9 H10 110.9(13) . . ? C10 C9 H10 108.1(12) . . ? C1 C10 C9 117.7(2) . . ? C1 C10 C5 121.0(2) . . ? C9 C10 C5 121.3(2) . . ? C6 C11 H13 109.5 . . ? C6 C11 H12 109.5 . . ? H13 C11 H12 109.5 . . ? C6 C11 H11 109.5 . . ? H13 C11 H11 109.5 . . ? H12 C11 H11 109.5 . . ? C6 C12 H14 109.5 . . ? C6 C12 H15 109.5 . . ? H14 C12 H15 109.5 . . ? C6 C12 H16 109.5 . . ? H14 C12 H16 109.5 . . ? H15 C12 H16 109.5 . . ? O3 C13 N1 121.1(2) . . ? O3 C13 C5 120.5(2) . . ? N1 C13 C5 118.5(2) . . ? N1 C14 C16 112.5(2) . . ? N1 C14 C15 108.1(2) . . ? C16 C14 C15 112.5(2) . . ? N1 C14 H17 105.2(13) . . ? C16 C14 H17 109.1(13) . . ? C15 C14 H17 109.2(13) . . ? C14 C15 H20 109.5 . . ? C14 C15 H18 109.5 . . ? H20 C15 H18 109.5 . . ? C14 C15 H19 109.5 . . ? H20 C15 H19 109.5 . . ? H18 C15 H19 109.5 . . ? C21 C16 C17 117.2(3) . . ? C21 C16 C14 122.5(3) . . ? C17 C16 C14 120.3(2) . . ? C18 C17 C16 121.8(3) . . ? C18 C17 H21 118.0(13) . . ? C16 C17 H21 120.2(13) . . ? C19 C18 C17 120.9(3) . . ? C19 C18 H22 118.0(17) . . ? C17 C18 H22 121.0(18) . . ? C18 C19 C20 118.9(4) . . ? C18 C19 H23 122.4(15) . . ? C20 C19 H23 118.7(16) . . ? C19 C20 C21 120.5(3) . . ? C19 C20 H24 119.8 . . ? C21 C20 H24 119.8 . . ? C16 C21 C20 120.7(3) . . ? C16 C21 H25 119.6 . . ? C20 C21 H25 119.6 . . ? 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 C10 C1 C2 O1 -177.2(3) . . . . ? C10 C1 C2 C3 0.9(4) . . . . ? O1 C2 C3 C4 -151.1(3) . . . . ? C1 C2 C3 C4 30.8(4) . . . . ? C2 C3 C4 C5 -59.2(3) . . . . ? C3 C4 C5 C10 53.9(3) . . . . ? C3 C4 C5 C13 -65.9(3) . . . . ? C3 C4 C5 C6 176.1(2) . . . . ? C10 C5 C6 C11 -165.8(2) . . . . ? C4 C5 C6 C11 73.6(2) . . . . ? C13 C5 C6 C11 -42.7(3) . . . . ? C10 C5 C6 C12 74.4(3) . . . . ? C4 C5 C6 C12 -46.2(3) . . . . ? C13 C5 C6 C12 -162.5(2) . . . . ? C10 C5 C6 C7 -45.0(3) . . . . ? C4 C5 C6 C7 -165.7(2) . . . . ? C13 C5 C6 C7 78.1(3) . . . . ? C11 C6 C7 C8 -178.0(2) . . . . ? C12 C6 C7 C8 -60.7(3) . . . . ? C5 C6 C7 C8 59.7(3) . . . . ? C6 C7 C8 C9 -59.2(3) . . . . ? C7 C8 C9 O2 -77.4(3) . . . . ? C7 C8 C9 C10 43.6(3) . . . . ? C2 C1 C10 C9 175.2(3) . . . . ? C2 C1 C10 C5 -4.9(4) . . . . ? O2 C9 C10 C1 -91.4(3) . . . . ? C8 C9 C10 C1 145.1(2) . . . . ? O2 C9 C10 C5 88.7(3) . . . . ? C8 C9 C10 C5 -34.8(3) . . . . ? C4 C5 C10 C1 -22.4(3) . . . . ? C13 C5 C10 C1 94.0(3) . . . . ? C6 C5 C10 C1 -144.5(2) . . . . ? C4 C5 C10 C9 157.5(2) . . . . ? C13 C5 C10 C9 -86.2(3) . . . . ? C6 C5 C10 C9 35.3(3) . . . . ? C14 N1 C13 O3 2.0(4) . . . . ? C14 N1 C13 C5 -178.3(2) . . . . ? C10 C5 C13 O3 -147.5(2) . . . . ? C4 C5 C13 O3 -29.7(3) . . . . ? C6 C5 C13 O3 89.7(3) . . . . ? C10 C5 C13 N1 32.9(3) . . . . ? C4 C5 C13 N1 150.6(2) . . . . ? C6 C5 C13 N1 -89.9(2) . . . . ? C13 N1 C14 C16 75.0(3) . . . . ? C13 N1 C14 C15 -160.2(2) . . . . ? N1 C14 C16 C21 24.1(4) . . . . ? C15 C14 C16 C21 -98.3(3) . . . . ? N1 C14 C16 C17 -156.6(2) . . . . ? C15 C14 C16 C17 81.0(3) . . . . ? C21 C16 C17 C18 0.2(4) . . . . ? C14 C16 C17 C18 -179.2(3) . . . . ? C16 C17 C18 C19 -0.3(5) . . . . ? C17 C18 C19 C20 0.3(5) . . . . ? C18 C19 C20 C21 -0.2(5) . . . . ? C17 C16 C21 C20 -0.1(4) . . . . ? C14 C16 C21 C20 179.2(3) . . . . ? C19 C20 C21 C16 0.1(5) . . . . ? _diffrn_measured_fraction_theta_max 0.960 _diffrn_reflns_theta_full 28.26 _diffrn_measured_fraction_theta_full 0.960 _refine_diff_density_max 0.209 _refine_diff_density_min -0.103 _refine_diff_density_rms 0.028 # Attachment '- 9.cif' data_cd26181 _database_code_depnum_ccdc_archive 'CCDC 838549' #TrackingRef '- 9.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H26 O6' _chemical_formula_weight 386.43 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 Monoclinic _symmetry_space_group_name_H-M Pn loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x+1/2, -y, z+1/2' _cell_length_a 10.5615(12) _cell_length_b 8.3727(9) _cell_length_c 11.8537(12) _cell_angle_alpha 90.00 _cell_angle_beta 108.972(2) _cell_angle_gamma 90.00 _cell_volume 991.26(18) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 858 _cell_measurement_theta_min 4.865 _cell_measurement_theta_max 39.967 _exptl_crystal_description prismatic _exptl_crystal_colour colorless _exptl_crystal_size_max 0.309 _exptl_crystal_size_mid 0.112 _exptl_crystal_size_min 0.060 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.295 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 412 _exptl_absorpt_coefficient_mu 0.094 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.76531 _exptl_absorpt_correction_T_max 1.00000 _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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5692 _diffrn_reflns_av_R_equivalents 0.0680 _diffrn_reflns_av_sigmaI/netI 0.0923 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.25 _diffrn_reflns_theta_max 27.00 _reflns_number_total 2159 _reflns_number_gt 1210 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0106P)^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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 10(10) _chemical_absolute_configuration ad _refine_ls_number_reflns 2159 _refine_ls_number_parameters 257 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0790 _refine_ls_R_factor_gt 0.0399 _refine_ls_wR_factor_ref 0.0581 _refine_ls_wR_factor_gt 0.0516 _refine_ls_goodness_of_fit_ref 0.764 _refine_ls_restrained_S_all 0.763 _refine_ls_shift/su_max 0.010 _refine_ls_shift/su_mean 0.002 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 0.0409(3) -0.0771(3) 0.3293(3) 0.1050(11) Uani 1 1 d . . . O2 O 0.4760(2) 0.2080(3) 0.2744(2) 0.0683(8) Uani 1 1 d . . . O3 O 0.3337(2) 0.2848(3) 0.09635(19) 0.0537(6) Uani 1 1 d . . . O4 O 0.6703(3) 0.1437(3) 0.1728(2) 0.0738(8) Uani 1 1 d . . . H4 H 0.6538 0.0901 0.2243 0.111 Uiso 1 1 calc R . . O5 O 0.1577(2) 0.0882(2) -0.14337(19) 0.0537(7) Uani 1 1 d . . . O6 O 0.2286(2) -0.0498(2) 0.02638(19) 0.0524(6) Uani 1 1 d . . . C1 C 0.1344(3) 0.1133(4) 0.2376(3) 0.0493(9) Uani 1 1 d . . . H1 H 0.1845 0.1570 0.3106 0.059 Uiso 1 1 calc R . . C2 C 0.0554(4) -0.0273(4) 0.2378(4) 0.0640(11) Uani 1 1 d . . . C3 C 0.0026(4) -0.1133(5) 0.1227(4) 0.0732(12) Uani 1 1 d . . . H3A H -0.0717 -0.1804 0.1242 0.088 Uiso 1 1 calc R . . H3B H 0.0720 -0.1821 0.1127 0.088 Uiso 1 1 calc R . . C4 C -0.0439(3) -0.0011(4) 0.0183(3) 0.0555(10) Uani 1 1 d . . . H4A H -0.1266 0.0484 0.0192 0.067 Uiso 1 1 calc R . . H4B H -0.0644 -0.0636 -0.0544 0.067 Uiso 1 1 calc R . . C5 C 0.0559(3) 0.1338(3) 0.0129(3) 0.0372(8) Uani 1 1 d . . . C6 C 0.1392(3) 0.1838(3) 0.1379(3) 0.0367(8) Uani 1 1 d . . . C7 C 0.2295(3) 0.3262(4) 0.1478(3) 0.0469(9) Uani 1 1 d . . . H7 H 0.2701 0.3569 0.2316 0.056 Uiso 1 1 calc R . . C8 C 0.1573(4) 0.4662(4) 0.0760(3) 0.0690(12) Uani 1 1 d . . . H8A H 0.2218 0.5481 0.0746 0.083 Uiso 1 1 calc R . . H8B H 0.0964 0.5110 0.1136 0.083 Uiso 1 1 calc R . . C9 C 0.0788(4) 0.4174(4) -0.0517(3) 0.0608(11) Uani 1 1 d . . . H9A H 0.1407 0.3823 -0.0916 0.073 Uiso 1 1 calc R . . H9B H 0.0306 0.5094 -0.0944 0.073 Uiso 1 1 calc R . . C10 C -0.0210(3) 0.2827(4) -0.0552(3) 0.0504(9) Uani 1 1 d . . . C11 C 0.4522(4) 0.2341(4) 0.1709(3) 0.0477(9) Uani 1 1 d . . . C12 C 0.5537(3) 0.2235(4) 0.1040(3) 0.0513(9) Uani 1 1 d . . . H12 H 0.5136 0.1653 0.0291 0.062 Uiso 1 1 calc R . . C13 C 0.5856(3) 0.3907(4) 0.0766(3) 0.0434(8) Uani 1 1 d . . . C14 C 0.6661(3) 0.4868(4) 0.1653(3) 0.0537(10) Uani 1 1 d . . . H14 H 0.7058 0.4462 0.2417 0.064 Uiso 1 1 calc R . . C15 C 0.6876(4) 0.6433(4) 0.1407(4) 0.0644(11) Uani 1 1 d . . . H15 H 0.7406 0.7081 0.2015 0.077 Uiso 1 1 calc R . . C16 C 0.6333(4) 0.7046(4) 0.0295(4) 0.0675(12) Uani 1 1 d . . . H16 H 0.6499 0.8100 0.0138 0.081 Uiso 1 1 calc R . . C17 C 0.5531(4) 0.6090(5) -0.0600(4) 0.0652(11) Uani 1 1 d . . . H17 H 0.5154 0.6493 -0.1368 0.078 Uiso 1 1 calc R . . C18 C 0.5291(3) 0.4538(4) -0.0353(3) 0.0566(10) Uani 1 1 d . . . H18 H 0.4736 0.3903 -0.0956 0.068 Uiso 1 1 calc R . . C19 C 0.1515(3) 0.0596(4) -0.0470(3) 0.0382(8) Uani 1 1 d . . . C20 C 0.3200(4) -0.1363(4) -0.0205(3) 0.0634(11) Uani 1 1 d . . . H20A H 0.2701 -0.2080 -0.0821 0.095 Uiso 1 1 calc R . . H20B H 0.3822 -0.1961 0.0426 0.095 Uiso 1 1 calc R . . H20C H 0.3682 -0.0619 -0.0529 0.095 Uiso 1 1 calc R . . C21 C -0.0997(4) 0.2456(5) -0.1872(3) 0.0834(13) Uani 1 1 d . . . H21A H -0.1594 0.3324 -0.2210 0.125 Uiso 1 1 calc R . . H21B H -0.1504 0.1493 -0.1919 0.125 Uiso 1 1 calc R . . H21C H -0.0381 0.2321 -0.2308 0.125 Uiso 1 1 calc R . . C22 C -0.1229(4) 0.3412(5) 0.0039(4) 0.0798(13) Uani 1 1 d . . . H22A H -0.0811 0.3442 0.0889 0.120 Uiso 1 1 calc R . . H22B H -0.1979 0.2695 -0.0157 0.120 Uiso 1 1 calc R . . H22C H -0.1533 0.4464 -0.0246 0.120 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 0.137(3) 0.105(2) 0.091(2) 0.0381(18) 0.061(2) -0.012(2) O2 0.073(2) 0.0842(19) 0.0538(18) 0.0230(14) 0.0286(16) 0.0129(15) O3 0.0470(17) 0.0679(16) 0.0482(15) -0.0047(13) 0.0182(14) -0.0153(13) O4 0.077(2) 0.0642(18) 0.093(2) 0.0333(16) 0.0457(17) 0.0232(15) O5 0.0750(18) 0.0520(15) 0.0435(15) 0.0024(12) 0.0322(13) 0.0065(13) O6 0.0596(17) 0.0531(15) 0.0518(15) 0.0076(12) 0.0283(14) 0.0210(13) C1 0.048(2) 0.058(3) 0.047(2) 0.0018(18) 0.0225(19) 0.0098(19) C2 0.067(3) 0.065(3) 0.075(3) 0.023(2) 0.043(3) 0.011(2) C3 0.079(3) 0.058(3) 0.097(3) 0.002(3) 0.047(3) -0.019(2) C4 0.047(2) 0.057(2) 0.066(3) -0.009(2) 0.023(2) -0.0097(18) C5 0.035(2) 0.0387(19) 0.040(2) -0.0011(15) 0.0154(17) 0.0000(15) C6 0.034(2) 0.0399(19) 0.042(2) 0.0020(16) 0.0200(17) 0.0061(15) C7 0.047(2) 0.048(2) 0.048(2) -0.0113(17) 0.0192(19) -0.0045(18) C8 0.084(3) 0.048(2) 0.082(3) 0.006(2) 0.036(3) -0.005(2) C9 0.070(3) 0.049(2) 0.064(3) 0.019(2) 0.022(2) 0.021(2) C10 0.046(2) 0.059(2) 0.047(2) 0.0078(18) 0.0162(19) 0.013(2) C11 0.057(3) 0.038(2) 0.050(2) 0.0008(17) 0.020(2) -0.0114(17) C12 0.061(3) 0.041(2) 0.059(2) 0.0004(18) 0.029(2) -0.0032(18) C13 0.046(2) 0.049(2) 0.044(2) 0.0027(18) 0.0261(18) 0.0015(18) C14 0.062(3) 0.058(2) 0.047(2) -0.001(2) 0.026(2) -0.009(2) C15 0.077(3) 0.056(3) 0.072(3) -0.014(2) 0.039(3) -0.016(2) C16 0.069(3) 0.054(3) 0.100(4) 0.007(3) 0.055(3) -0.001(2) C17 0.060(3) 0.068(3) 0.071(3) 0.030(2) 0.026(2) 0.009(2) C18 0.053(3) 0.063(3) 0.055(3) 0.0054(19) 0.020(2) -0.0010(19) C19 0.042(2) 0.0382(19) 0.036(2) -0.0072(16) 0.0154(18) -0.0083(16) C20 0.060(3) 0.064(3) 0.073(3) -0.003(2) 0.030(2) 0.021(2) C21 0.062(3) 0.110(3) 0.065(3) 0.016(2) 0.003(2) 0.020(2) C22 0.067(3) 0.084(3) 0.096(3) 0.011(2) 0.037(3) 0.039(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 C2 1.216(4) . ? O2 C11 1.190(4) . ? O3 C11 1.345(4) . ? O3 C7 1.463(3) . ? O4 C12 1.406(4) . ? O4 H4 0.8200 . ? O5 C19 1.189(3) . ? O6 C19 1.342(3) . ? O6 C20 1.454(3) . ? C1 C6 1.337(4) . ? C1 C2 1.443(4) . ? C1 H1 0.9300 . ? C2 C3 1.483(5) . ? C3 C4 1.503(4) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 C5 1.560(4) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C5 C6 1.516(4) . ? C5 C19 1.542(4) . ? C5 C10 1.562(4) . ? C6 C7 1.507(4) . ? C7 C8 1.503(4) . ? C7 H7 0.9800 . ? C8 C9 1.526(5) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 C10 1.534(4) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 C22 1.543(4) . ? C10 C21 1.546(4) . ? C11 C12 1.529(4) . ? C12 C13 1.500(4) . ? C12 H12 0.9800 . ? C13 C18 1.371(4) . ? C13 C14 1.377(4) . ? C14 C15 1.377(5) . ? C14 H14 0.9300 . ? C15 C16 1.356(5) . ? C15 H15 0.9300 . ? C16 C17 1.379(5) . ? C16 H16 0.9300 . ? C17 C18 1.373(4) . ? C17 H17 0.9300 . ? C18 H18 0.9300 . ? C20 H20A 0.9600 . ? C20 H20B 0.9600 . ? C20 H20C 0.9600 . ? C21 H21A 0.9600 . ? C21 H21B 0.9600 . ? C21 H21C 0.9600 . ? C22 H22A 0.9600 . ? C22 H22B 0.9600 . ? C22 H22C 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 C11 O3 C7 117.8(3) . . ? C12 O4 H4 109.5 . . ? C19 O6 C20 115.5(2) . . ? C6 C1 C2 123.4(3) . . ? C6 C1 H1 118.3 . . ? C2 C1 H1 118.3 . . ? O1 C2 C1 121.4(4) . . ? O1 C2 C3 122.4(4) . . ? C1 C2 C3 116.0(3) . . ? C2 C3 C4 112.3(3) . . ? C2 C3 H3A 109.2 . . ? C4 C3 H3A 109.2 . . ? C2 C3 H3B 109.2 . . ? C4 C3 H3B 109.2 . . ? H3A C3 H3B 107.9 . . ? C3 C4 C5 116.2(3) . . ? C3 C4 H4A 108.2 . . ? C5 C4 H4A 108.2 . . ? C3 C4 H4B 108.2 . . ? C5 C4 H4B 108.2 . . ? H4A C4 H4B 107.4 . . ? C6 C5 C19 107.6(2) . . ? C6 C5 C4 110.2(2) . . ? C19 C5 C4 106.2(2) . . ? C6 C5 C10 108.9(2) . . ? C19 C5 C10 113.0(2) . . ? C4 C5 C10 110.8(2) . . ? C1 C6 C7 119.1(3) . . ? C1 C6 C5 124.4(3) . . ? C7 C6 C5 116.5(3) . . ? O3 C7 C8 105.1(3) . . ? O3 C7 C6 108.9(2) . . ? C8 C7 C6 112.4(3) . . ? O3 C7 H7 110.1 . . ? C8 C7 H7 110.1 . . ? C6 C7 H7 110.1 . . ? C7 C8 C9 111.4(3) . . ? C7 C8 H8A 109.3 . . ? C9 C8 H8A 109.3 . . ? C7 C8 H8B 109.3 . . ? C9 C8 H8B 109.3 . . ? H8A C8 H8B 108.0 . . ? C8 C9 C10 111.8(3) . . ? C8 C9 H9A 109.3 . . ? C10 C9 H9A 109.3 . . ? C8 C9 H9B 109.3 . . ? C10 C9 H9B 109.3 . . ? H9A C9 H9B 107.9 . . ? C9 C10 C22 109.2(3) . . ? C9 C10 C21 108.3(3) . . ? C22 C10 C21 107.4(3) . . ? C9 C10 C5 109.6(3) . . ? C22 C10 C5 109.9(3) . . ? C21 C10 C5 112.4(3) . . ? O2 C11 O3 125.1(3) . . ? O2 C11 C12 125.1(4) . . ? O3 C11 C12 109.7(3) . . ? O4 C12 C13 110.7(3) . . ? O4 C12 C11 110.9(3) . . ? C13 C12 C11 107.6(3) . . ? O4 C12 H12 109.2 . . ? C13 C12 H12 109.2 . . ? C11 C12 H12 109.2 . . ? C18 C13 C14 118.7(3) . . ? C18 C13 C12 120.8(3) . . ? C14 C13 C12 120.4(3) . . ? C13 C14 C15 119.9(3) . . ? C13 C14 H14 120.1 . . ? C15 C14 H14 120.1 . . ? C16 C15 C14 121.3(4) . . ? C16 C15 H15 119.3 . . ? C14 C15 H15 119.3 . . ? C15 C16 C17 119.2(4) . . ? C15 C16 H16 120.4 . . ? C17 C16 H16 120.4 . . ? C18 C17 C16 119.7(4) . . ? C18 C17 H17 120.2 . . ? C16 C17 H17 120.2 . . ? C17 C18 C13 121.3(4) . . ? C17 C18 H18 119.4 . . ? C13 C18 H18 119.4 . . ? O5 C19 O6 123.3(3) . . ? O5 C19 C5 127.6(3) . . ? O6 C19 C5 109.1(3) . . ? O6 C20 H20A 109.5 . . ? O6 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? O6 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C10 C21 H21A 109.5 . . ? C10 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C10 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C10 C22 H22A 109.5 . . ? C10 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C10 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 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 O1 -171.2(4) . . . . ? C6 C1 C2 C3 13.4(5) . . . . ? O1 C2 C3 C4 145.3(4) . . . . ? C1 C2 C3 C4 -39.3(5) . . . . ? C2 C3 C4 C5 49.6(4) . . . . ? C3 C4 C5 C6 -31.9(4) . . . . ? C3 C4 C5 C19 84.5(4) . . . . ? C3 C4 C5 C10 -152.4(3) . . . . ? C2 C1 C6 C7 -177.5(3) . . . . ? C2 C1 C6 C5 4.6(5) . . . . ? C19 C5 C6 C1 -110.7(3) . . . . ? C4 C5 C6 C1 4.8(4) . . . . ? C10 C5 C6 C1 126.5(3) . . . . ? C19 C5 C6 C7 71.3(3) . . . . ? C4 C5 C6 C7 -173.3(2) . . . . ? C10 C5 C6 C7 -51.5(3) . . . . ? C11 O3 C7 C8 143.8(3) . . . . ? C11 O3 C7 C6 -95.5(3) . . . . ? C1 C6 C7 O3 115.6(3) . . . . ? C5 C6 C7 O3 -66.3(3) . . . . ? C1 C6 C7 C8 -128.4(3) . . . . ? C5 C6 C7 C8 49.7(3) . . . . ? O3 C7 C8 C9 68.4(3) . . . . ? C6 C7 C8 C9 -49.9(4) . . . . ? C7 C8 C9 C10 56.6(4) . . . . ? C8 C9 C10 C22 61.2(4) . . . . ? C8 C9 C10 C21 177.8(3) . . . . ? C8 C9 C10 C5 -59.2(3) . . . . ? C6 C5 C10 C9 54.8(3) . . . . ? C19 C5 C10 C9 -64.8(3) . . . . ? C4 C5 C10 C9 176.1(3) . . . . ? C6 C5 C10 C22 -65.2(3) . . . . ? C19 C5 C10 C22 175.2(3) . . . . ? C4 C5 C10 C22 56.1(4) . . . . ? C6 C5 C10 C21 175.3(3) . . . . ? C19 C5 C10 C21 55.7(4) . . . . ? C4 C5 C10 C21 -63.4(3) . . . . ? C7 O3 C11 O2 6.3(5) . . . . ? C7 O3 C11 C12 -170.8(2) . . . . ? O2 C11 C12 O4 13.7(5) . . . . ? O3 C11 C12 O4 -169.2(3) . . . . ? O2 C11 C12 C13 -107.5(4) . . . . ? O3 C11 C12 C13 69.6(3) . . . . ? O4 C12 C13 C18 136.9(3) . . . . ? C11 C12 C13 C18 -101.7(3) . . . . ? O4 C12 C13 C14 -46.9(4) . . . . ? C11 C12 C13 C14 74.4(4) . . . . ? C18 C13 C14 C15 0.4(5) . . . . ? C12 C13 C14 C15 -175.9(3) . . . . ? C13 C14 C15 C16 -1.4(5) . . . . ? C14 C15 C16 C17 1.0(6) . . . . ? C15 C16 C17 C18 0.3(5) . . . . ? C16 C17 C18 C13 -1.2(5) . . . . ? C14 C13 C18 C17 0.9(5) . . . . ? C12 C13 C18 C17 177.2(3) . . . . ? C20 O6 C19 O5 -1.5(4) . . . . ? C20 O6 C19 C5 177.1(3) . . . . ? C6 C5 C19 O5 -131.8(3) . . . . ? C4 C5 C19 O5 110.2(4) . . . . ? C10 C5 C19 O5 -11.5(5) . . . . ? C6 C5 C19 O6 49.8(3) . . . . ? C4 C5 C19 O6 -68.2(3) . . . . ? C10 C5 C19 O6 170.1(2) . . . . ? 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 O5 0.82 2.16 2.954(3) 164.0 2 _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 27.00 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.116 _refine_diff_density_min -0.123 _refine_diff_density_rms 0.033