# Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2008 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _publ_contact_author_name 'Zhen Yang' _publ_contact_author_email ZYANG@PKU.EDU.CN _publ_section_title ; A Model Study for the Concise Construction of the Cortistatins Oxapentacyclic Core through Intramolecular Diels-Alder Reaction and Oxidative Dearomatization Cyclization ; loop_ _publ_author_name 'Zhen Yang' 'Chao Che' 'Yingxiang Gao' 'Chuang-Chuang Li' 'Lianzhu Liu' 'David Zhigang Wang' 'Na Wu' # Attachment 'cif-11' data_gjx-c _database_code_depnum_ccdc_archive 'CCDC 699943' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C23 H30 O6' _chemical_formula_weight 402.47 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 P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.306(2) _cell_length_b 11.417(2) _cell_length_c 11.436(2) _cell_angle_alpha 105.05(3) _cell_angle_beta 111.60(3) _cell_angle_gamma 110.32(3) _cell_volume 1051.0(4) _cell_formula_units_Z 2 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 18609 _cell_measurement_theta_min 2.14 _cell_measurement_theta_max 27.48 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.50 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.272 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 432 _exptl_absorpt_coefficient_mu 0.091 _exptl_absorpt_correction_type Empirical _exptl_absorpt_correction_T_min 0.9559 _exptl_absorpt_correction_T_max 0.9732 _exptl_absorpt_process_details ; HIGASHI, T. (1995). Abscor-Empirical Absorption Correction based on Fourier Series Approximation. Rigaku Corporation,Tokyo,Japan. ; _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 'Rigaku RAXIS RAPID IP' _diffrn_measurement_method \W _diffrn_detector_area_resol_mean 10.00 _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 18609 _diffrn_reflns_av_R_equivalents 0.03887667 _diffrn_reflns_av_sigmaI/netI 0.0681 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.14 _diffrn_reflns_theta_max 27.48 _reflns_number_total 4681 _reflns_number_gt 2569 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Rapid-AUTO (Rigaku,2000)' _computing_cell_refinement Rapid-AUTO _computing_data_reduction 'CrystalStructure (Rigaku/MSC,2000)' _computing_structure_solution SHELXS-97,(Sheldrick,1997) _computing_structure_refinement SHELXL-97,(Sheldrick,1997) _computing_molecular_graphics 'Siemens SHELXTL V4.2,(Sheldrick,1990)' _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^)+(0.0550P)^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 0.069(4) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 4681 _refine_ls_number_parameters 281 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0978 _refine_ls_R_factor_gt 0.0502 _refine_ls_wR_factor_ref 0.1174 _refine_ls_wR_factor_gt 0.1068 _refine_ls_goodness_of_fit_ref 0.993 _refine_ls_restrained_S_all 0.993 _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 0.86653(19) 0.64247(18) 0.59854(16) 0.0332(4) Uani 1 1 d . . . C2 C 1.03158(18) 0.76563(17) 0.67683(17) 0.0343(4) Uani 1 1 d . . . C3 C 1.13678(19) 0.85269(18) 0.81151(17) 0.0382(4) Uani 1 1 d . . . C4 C 1.2824(2) 0.9562(2) 0.8127(2) 0.0505(5) Uani 1 1 d . . . C5 C 1.3603(2) 0.8760(2) 0.7678(2) 0.0561(6) Uani 1 1 d . . . H5 H 1.4605 0.8871 0.8225 0.067 Uiso 1 1 calc R . . C6 C 1.2555(2) 0.7874(2) 0.6349(2) 0.0490(5) Uani 1 1 d . . . H6 H 1.2651 0.7212 0.5766 0.059 Uiso 1 1 calc R . . C7 C 1.11434(19) 0.81610(18) 0.59611(17) 0.0381(4) Uani 1 1 d . . . C8 C 1.0073(2) 0.7744(2) 0.44519(18) 0.0444(5) Uani 1 1 d . . . H8A H 0.9697 0.6766 0.3915 0.053 Uiso 1 1 calc R . . H8B H 1.0706 0.8272 0.4131 0.053 Uiso 1 1 calc R . . C9 C 0.86111(19) 0.7954(2) 0.41190(19) 0.0428(5) Uani 1 1 d . . . H9A H 0.8308 0.8067 0.3263 0.051 Uiso 1 1 calc R . . H9B H 0.8944 0.8824 0.4866 0.051 Uiso 1 1 calc R . . C10 C 0.70960(19) 0.68105(17) 0.39343(16) 0.0350(4) Uani 1 1 d . . . C11 C 0.56972(19) 0.71060(19) 0.33342(18) 0.0407(4) Uani 1 1 d . . . C12 C 0.3990(2) 0.5892(2) 0.2647(2) 0.0516(5) Uani 1 1 d . . . H12A H 0.3935 0.5382 0.3202 0.062 Uiso 1 1 calc R . . H12B H 0.3645 0.5255 0.1709 0.062 Uiso 1 1 calc R . . C13 C 0.2950(2) 0.6591(2) 0.2597(2) 0.0588(6) Uani 1 1 d . . . H13A H 0.2306 0.6427 0.1643 0.071 Uiso 1 1 calc R . . H13B H 0.2237 0.6215 0.2930 0.071 Uiso 1 1 calc R . . C14 C 0.4088(2) 0.8146(2) 0.3541(2) 0.0588(6) Uani 1 1 d . . . H14A H 0.3742 0.8505 0.4165 0.071 Uiso 1 1 calc R . . H14B H 0.4133 0.8656 0.2985 0.071 Uiso 1 1 calc R . . C15 C 0.5735(2) 0.8282(2) 0.4383(2) 0.0452(5) Uani 1 1 d . . . C16 C 0.5951(2) 0.8094(2) 0.57010(19) 0.0515(5) Uani 1 1 d . . . H16A H 0.6076 0.8899 0.6383 0.062 Uiso 1 1 calc R . . H16B H 0.5002 0.7278 0.5467 0.062 Uiso 1 1 calc R . . C17 C 0.7415(2) 0.7921(2) 0.63409(17) 0.0457(5) Uani 1 1 d . . . H17A H 0.7514 0.7786 0.7166 0.055 Uiso 1 1 calc R . . H17B H 0.8372 0.8764 0.6634 0.055 Uiso 1 1 calc R . . C18 C 0.72928(19) 0.66809(18) 0.52979(16) 0.0342(4) Uani 1 1 d . . . C19 C 1.1335(2) 0.8555(2) 0.93914(18) 0.0451(5) Uani 1 1 d . . . C20 C 0.9787(3) 0.7537(2) 1.0337(2) 0.0627(6) Uani 1 1 d . . . H20A H 1.0836 0.8018 1.1176 0.075 Uiso 1 1 calc R . . H20B H 0.9245 0.6577 1.0176 0.075 Uiso 1 1 calc R . . C21 C 0.8843(3) 0.8214(3) 1.0533(3) 0.0911(8) Uani 1 1 d . . . H21A H 0.9429 0.9184 1.0775 0.137 Uiso 1 1 calc R . . H21B H 0.8652 0.8122 1.1274 0.137 Uiso 1 1 calc R . . H21C H 0.7836 0.7775 0.9678 0.137 Uiso 1 1 calc R . . C22 C 0.6249(3) 0.5115(3) 0.16085(19) 0.0624(6) Uani 1 1 d . . . H22A H 0.5396 0.4153 0.1030 0.075 Uiso 1 1 calc R . . H22B H 0.5818 0.5698 0.1344 0.075 Uiso 1 1 calc R . . C23 C 0.7946(3) 0.4262(3) 0.1373(2) 0.0806(7) Uani 1 1 d . . . H23A H 0.8313 0.4305 0.2294 0.121 Uiso 1 1 calc R . . H23B H 0.8798 0.4433 0.1166 0.121 Uiso 1 1 calc R . . H23C H 0.7047 0.3353 0.0694 0.121 Uiso 1 1 calc R . . O1 O 0.84807(14) 0.52923(13) 0.58909(13) 0.0510(4) Uani 1 1 d . . . O2 O 1.24408(17) 0.93832(18) 1.05468(14) 0.0918(6) Uani 1 1 d . . . O3 O 0.99643(14) 0.75795(14) 0.91388(12) 0.0554(4) Uani 1 1 d . . . O4 O 0.67081(13) 0.54412(12) 0.30240(11) 0.0432(3) Uani 1 1 d . . . O5 O 0.74730(17) 0.52915(15) 0.13219(13) 0.0619(4) Uani 1 1 d . . . O48 O 1.19884(14) 0.96510(13) 0.68561(13) 0.0491(3) Uani 1 1 d . . . H4 H 1.346(2) 1.051(2) 0.8934(19) 0.053(5) Uiso 1 1 d . . . H18 H 0.6285(19) 0.5832(18) 0.4985(16) 0.044(5) Uiso 1 1 d . . . H15 H 0.665(2) 0.919(2) 0.4639(18) 0.055(5) Uiso 1 1 d . . . H11 H 0.5775(18) 0.7392(17) 0.2599(17) 0.041(5) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0366(9) 0.0369(10) 0.0300(8) 0.0185(8) 0.0199(7) 0.0159(8) C2 0.0328(9) 0.0380(10) 0.0400(9) 0.0216(8) 0.0207(8) 0.0196(8) C3 0.0329(9) 0.0411(11) 0.0379(9) 0.0166(8) 0.0176(8) 0.0167(8) C4 0.0372(11) 0.0483(13) 0.0438(11) 0.0158(10) 0.0138(9) 0.0099(9) C5 0.0337(10) 0.0731(15) 0.0605(13) 0.0332(12) 0.0247(10) 0.0219(10) C6 0.0406(11) 0.0617(14) 0.0585(12) 0.0314(11) 0.0322(10) 0.0278(10) C7 0.0349(9) 0.0394(11) 0.0429(9) 0.0201(9) 0.0237(8) 0.0155(8) C8 0.0407(10) 0.0573(12) 0.0444(10) 0.0280(9) 0.0281(9) 0.0225(9) C9 0.0427(10) 0.0526(12) 0.0454(10) 0.0320(9) 0.0270(9) 0.0230(9) C10 0.0382(9) 0.0378(10) 0.0328(8) 0.0181(8) 0.0197(8) 0.0188(8) C11 0.0369(10) 0.0530(12) 0.0427(10) 0.0301(9) 0.0218(9) 0.0243(9) C12 0.0399(11) 0.0562(13) 0.0495(11) 0.0232(10) 0.0161(9) 0.0220(10) C13 0.0445(12) 0.0751(16) 0.0634(13) 0.0398(12) 0.0249(11) 0.0321(11) C14 0.0569(13) 0.0727(16) 0.0729(14) 0.0452(13) 0.0372(12) 0.0436(12) C15 0.0415(11) 0.0449(12) 0.0568(11) 0.0260(10) 0.0265(10) 0.0248(9) C16 0.0520(12) 0.0631(14) 0.0511(11) 0.0232(10) 0.0310(10) 0.0361(10) C17 0.0459(11) 0.0580(13) 0.0393(10) 0.0211(9) 0.0244(9) 0.0289(10) C18 0.0308(9) 0.0367(10) 0.0345(9) 0.0182(8) 0.0181(8) 0.0128(8) C19 0.0390(11) 0.0496(12) 0.0375(10) 0.0171(9) 0.0146(9) 0.0195(9) C20 0.0657(14) 0.0784(16) 0.0493(11) 0.0359(11) 0.0341(11) 0.0298(12) C21 0.130(2) 0.102(2) 0.0889(18) 0.0510(16) 0.0823(18) 0.0699(19) C22 0.0692(14) 0.0875(17) 0.0359(10) 0.0230(11) 0.0230(10) 0.0509(13) C23 0.1047(19) 0.095(2) 0.0770(16) 0.0399(15) 0.0535(15) 0.0736(17) O1 0.0512(8) 0.0399(8) 0.0571(8) 0.0267(7) 0.0218(7) 0.0201(6) O2 0.0570(10) 0.1061(14) 0.0385(8) 0.0206(9) 0.0075(8) -0.0057(9) O3 0.0451(8) 0.0703(10) 0.0393(7) 0.0221(7) 0.0231(6) 0.0169(7) O4 0.0491(7) 0.0474(8) 0.0324(6) 0.0163(6) 0.0196(6) 0.0252(6) O5 0.0882(10) 0.0795(11) 0.0523(8) 0.0397(8) 0.0470(8) 0.0552(9) O48 0.0467(7) 0.0403(8) 0.0537(8) 0.0241(6) 0.0247(6) 0.0133(6) _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 1.2087(19) . ? C1 C2 1.495(2) . ? C1 C18 1.514(2) . ? C2 C3 1.328(2) . ? C2 C7 1.558(2) . ? C3 C19 1.465(2) . ? C3 C4 1.548(3) . ? C4 O48 1.442(2) . ? C4 C5 1.522(3) . ? C4 H4 0.998(19) . ? C5 C6 1.316(3) . ? C5 H5 0.9300 . ? C6 C7 1.533(2) . ? C6 H6 0.9300 . ? C7 O48 1.453(2) . ? C7 C8 1.493(2) . ? C8 C9 1.533(2) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 C10 1.544(2) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 O4 1.450(2) . ? C10 C11 1.547(2) . ? C10 C18 1.550(2) . ? C11 C15 1.529(3) . ? C11 C12 1.535(3) . ? C11 H11 0.997(17) . ? C12 C13 1.536(3) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C13 C14 1.523(3) . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C14 C15 1.539(3) . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C15 C16 1.524(3) . ? C15 H15 1.006(19) . ? C16 C17 1.523(2) . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? C17 C18 1.527(3) . ? C17 H17A 0.9700 . ? C17 H17B 0.9700 . ? C18 H18 0.997(16) . ? C19 O2 1.197(2) . ? C19 O3 1.327(2) . ? C20 O3 1.459(2) . ? C20 C21 1.479(3) . ? C20 H20A 0.9700 . ? C20 H20B 0.9700 . ? C21 H21A 0.9600 . ? C21 H21B 0.9600 . ? C21 H21C 0.9600 . ? C22 O5 1.379(2) . ? C22 O4 1.409(2) . ? C22 H22A 0.9700 . ? C22 H22B 0.9700 . ? C23 O5 1.427(3) . ? C23 H23A 0.9600 . ? C23 H23B 0.9600 . ? C23 H23C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 C1 C2 120.28(15) . . ? O1 C1 C18 123.38(15) . . ? C2 C1 C18 116.30(14) . . ? C3 C2 C1 134.40(15) . . ? C3 C2 C7 105.22(14) . . ? C1 C2 C7 120.38(14) . . ? C2 C3 C19 131.55(16) . . ? C2 C3 C4 104.86(15) . . ? C19 C3 C4 123.49(16) . . ? O48 C4 C5 100.69(16) . . ? O48 C4 C3 99.31(14) . . ? C5 C4 C3 107.40(16) . . ? O48 C4 H4 109.0(11) . . ? C5 C4 H4 122.3(11) . . ? C3 C4 H4 114.7(11) . . ? C6 C5 C4 105.19(17) . . ? C6 C5 H5 127.4 . . ? C4 C5 H5 127.4 . . ? C5 C6 C7 105.81(18) . . ? C5 C6 H6 127.1 . . ? C7 C6 H6 127.1 . . ? O48 C7 C8 114.05(15) . . ? O48 C7 C6 100.22(14) . . ? C8 C7 C6 118.33(15) . . ? O48 C7 C2 98.37(13) . . ? C8 C7 C2 116.88(14) . . ? C6 C7 C2 106.01(13) . . ? C7 C8 C9 115.78(15) . . ? C7 C8 H8A 108.3 . . ? C9 C8 H8A 108.3 . . ? C7 C8 H8B 108.3 . . ? C9 C8 H8B 108.3 . . ? H8A C8 H8B 107.4 . . ? C8 C9 C10 118.12(15) . . ? C8 C9 H9A 107.8 . . ? C10 C9 H9A 107.8 . . ? C8 C9 H9B 107.8 . . ? C10 C9 H9B 107.8 . . ? H9A C9 H9B 107.1 . . ? O4 C10 C9 110.60(14) . . ? O4 C10 C11 111.26(13) . . ? C9 C10 C11 108.66(14) . . ? O4 C10 C18 102.42(13) . . ? C9 C10 C18 114.47(14) . . ? C11 C10 C18 109.35(14) . . ? C15 C11 C12 103.30(15) . . ? C15 C11 C10 115.60(14) . . ? C12 C11 C10 117.08(15) . . ? C15 C11 H11 106.8(10) . . ? C12 C11 H11 107.2(9) . . ? C10 C11 H11 106.3(9) . . ? C11 C12 C13 104.53(16) . . ? C11 C12 H12A 110.8 . . ? C13 C12 H12A 110.8 . . ? C11 C12 H12B 110.8 . . ? C13 C12 H12B 110.8 . . ? H12A C12 H12B 108.9 . . ? C14 C13 C12 107.10(16) . . ? C14 C13 H13A 110.3 . . ? C12 C13 H13A 110.3 . . ? C14 C13 H13B 110.3 . . ? C12 C13 H13B 110.3 . . ? H13A C13 H13B 108.6 . . ? C13 C14 C15 105.26(17) . . ? C13 C14 H14A 110.7 . . ? C15 C14 H14A 110.7 . . ? C13 C14 H14B 110.7 . . ? C15 C14 H14B 110.7 . . ? H14A C14 H14B 108.8 . . ? C16 C15 C11 111.36(16) . . ? C16 C15 C14 112.12(16) . . ? C11 C15 C14 102.55(16) . . ? C16 C15 H15 109.9(10) . . ? C11 C15 H15 108.5(11) . . ? C14 C15 H15 112.2(11) . . ? C17 C16 C15 110.97(15) . . ? C17 C16 H16A 109.4 . . ? C15 C16 H16A 109.4 . . ? C17 C16 H16B 109.4 . . ? C15 C16 H16B 109.4 . . ? H16A C16 H16B 108.0 . . ? C16 C17 C18 111.54(15) . . ? C16 C17 H17A 109.3 . . ? C18 C17 H17A 109.3 . . ? C16 C17 H17B 109.3 . . ? C18 C17 H17B 109.3 . . ? H17A C17 H17B 108.0 . . ? C1 C18 C17 111.22(14) . . ? C1 C18 C10 113.28(14) . . ? C17 C18 C10 112.20(14) . . ? C1 C18 H18 106.9(10) . . ? C17 C18 H18 108.1(10) . . ? C10 C18 H18 104.7(9) . . ? O2 C19 O3 123.59(17) . . ? O2 C19 C3 122.96(18) . . ? O3 C19 C3 113.45(15) . . ? O3 C20 C21 109.30(18) . . ? O3 C20 H20A 109.8 . . ? C21 C20 H20A 109.8 . . ? O3 C20 H20B 109.8 . . ? C21 C20 H20B 109.8 . . ? H20A C20 H20B 108.3 . . ? C20 C21 H21A 109.5 . . ? C20 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C20 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? O5 C22 O4 114.41(16) . . ? O5 C22 H22A 108.7 . . ? O4 C22 H22A 108.7 . . ? O5 C22 H22B 108.7 . . ? O4 C22 H22B 108.7 . . ? H22A C22 H22B 107.6 . . ? O5 C23 H23A 109.5 . . ? O5 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? O5 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? C19 O3 C20 118.01(15) . . ? C22 O4 C10 118.37(15) . . ? C22 O5 C23 113.00(18) . . ? C4 O48 C7 94.95(14) . . ? _diffrn_measured_fraction_theta_max 0.972 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.972 _refine_diff_density_max 0.291 _refine_diff_density_min -0.331 _refine_diff_density_rms 0.077 # Attachment '18a.cif.txt' data_lcc2a _database_code_depnum_ccdc_archive 'CCDC 700771' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C21 H26 O5' _chemical_formula_weight 358.42 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)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 9.2758(19) _cell_length_b 9.802(2) _cell_length_c 20.869(4) _cell_angle_alpha 90.00 _cell_angle_beta 102.05(3) _cell_angle_gamma 90.00 _cell_volume 1855.7(7) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 16217 _cell_measurement_theta_min 2.26 _cell_measurement_theta_max 27.48 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.50 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.283 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 768 _exptl_absorpt_coefficient_mu 0.091 _exptl_absorpt_correction_type Empirical _exptl_absorpt_correction_T_min 0.9477 _exptl_absorpt_correction_T_max 0.9733 _exptl_absorpt_process_details ; HIGASHI, T. (1995). Abscor-Empirical Absorption Correction based on Fourier Series Approximation. Rigaku Corporation,Tokyo,Japan. ; _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 'Rigaku RAXIS RAPID IP' _diffrn_measurement_method \W _diffrn_detector_area_resol_mean 10.00 _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 16217 _diffrn_reflns_av_R_equivalents 0.05105433 _diffrn_reflns_av_sigmaI/netI 0.1012 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 2.26 _diffrn_reflns_theta_max 27.48 _reflns_number_total 4238 _reflns_number_gt 1808 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Rapid-AUTO (Rigaku,2000)' _computing_cell_refinement Rapid-AUTO _computing_data_reduction 'CrystalStructure (Rigaku/MSC,2000)' _computing_structure_solution SHELXS-97,(Sheldrick,1997) _computing_structure_refinement SHELXL-97,(Sheldrick,1997) _computing_molecular_graphics 'Siemens SHELXTL V4.2,(Sheldrick,1990)' _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^)+(0.0200P)^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 0.0344(12) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 4238 _refine_ls_number_parameters 251 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1200 _refine_ls_R_factor_gt 0.0456 _refine_ls_wR_factor_ref 0.0845 _refine_ls_wR_factor_gt 0.0769 _refine_ls_goodness_of_fit_ref 0.989 _refine_ls_restrained_S_all 0.989 _refine_ls_shift/su_max 0.002 _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 0.05157(16) 0.95659(12) 0.06527(7) 0.0664(4) Uani 1 1 d . . . H3 H 0.1299 0.9955 0.0796 0.100 Uiso 1 1 calc R . . O5 O 0.25371(14) 0.74388(12) 0.30098(5) 0.0482(3) Uani 1 1 d . . . C1 C 0.0865(2) 0.83455(19) 0.19378(8) 0.0427(5) Uani 1 1 d . . . O1 O 0.10148(15) 0.95064(13) 0.21467(6) 0.0617(4) Uani 1 1 d . . . C10 C 0.0727(2) 0.81138(17) 0.07175(8) 0.0443(5) Uani 1 1 d . . . C17 C 0.2083(2) 0.63207(17) 0.14932(8) 0.0456(5) Uani 1 1 d . . . H17A H 0.2678 0.6174 0.1928 0.055 Uiso 1 1 calc R . . H17B H 0.1205 0.5762 0.1449 0.055 Uiso 1 1 calc R . . C18 C 0.1638(2) 0.78259(18) 0.14143(8) 0.0391(5) Uani 1 1 d . . . C2 C -0.0206(2) 0.73899(19) 0.21572(9) 0.0450(5) Uani 1 1 d . . . C11 C 0.1549(2) 0.7590(2) 0.01994(9) 0.0486(5) Uani 1 1 d . . . C19 C 0.1482(2) 0.68610(19) 0.32543(10) 0.0524(5) Uani 1 1 d . . . C3 C 0.0071(2) 0.67393(19) 0.27755(10) 0.0477(5) Uani 1 1 d . . . C9 C -0.08185(19) 0.7483(2) 0.05911(9) 0.0579(6) Uani 1 1 d . . . H9A H -0.0712 0.6499 0.0611 0.070 Uiso 1 1 calc R . . H9B H -0.1315 0.7714 0.0148 0.070 Uiso 1 1 calc R . . C15 C 0.2093(2) 0.6116(2) 0.02891(9) 0.0482(5) Uani 1 1 d . . . C20 C 0.3988(2) 0.7548(2) 0.34361(9) 0.0549(6) Uani 1 1 d . . . H20A H 0.4322 0.6662 0.3615 0.066 Uiso 1 1 calc R . . H20B H 0.3961 0.8167 0.3796 0.066 Uiso 1 1 calc R . . C16 C 0.29515(19) 0.5886(2) 0.09846(9) 0.0536(5) Uani 1 1 d . . . H16A H 0.3865 0.6398 0.1052 0.064 Uiso 1 1 calc R . . H16B H 0.3199 0.4926 0.1044 0.064 Uiso 1 1 calc R . . O4 O 0.16789(17) 0.64455(17) 0.38150(7) 0.0828(5) Uani 1 1 d . . . C8 C -0.1823(2) 0.7908(2) 0.10582(10) 0.0695(7) Uani 1 1 d . . . H8A H -0.1723 0.8883 0.1132 0.083 Uiso 1 1 calc R . . H8B H -0.2838 0.7732 0.0843 0.083 Uiso 1 1 calc R . . C4 C -0.1024(3) 0.5903(2) 0.29410(12) 0.0649(6) Uani 1 1 d . . . C7 C -0.1524(2) 0.7204(2) 0.17120(10) 0.0568(6) Uani 1 1 d . . . C21 C 0.4990(2) 0.8082(2) 0.30197(10) 0.0728(7) Uani 1 1 d . . . H21A H 0.5020 0.7449 0.2672 0.109 Uiso 1 1 calc R . . H21B H 0.5963 0.8195 0.3282 0.109 Uiso 1 1 calc R . . H21C H 0.4629 0.8947 0.2837 0.109 Uiso 1 1 calc R . . C12 C 0.2914(3) 0.8373(2) 0.01075(10) 0.0755(7) Uani 1 1 d . . . H12A H 0.3521 0.8630 0.0527 0.091 Uiso 1 1 calc R . . H12B H 0.2640 0.9190 -0.0152 0.091 Uiso 1 1 calc R . . C6 C -0.2583(2) 0.6350(3) 0.18977(14) 0.0787(8) Uani 1 1 d . . . H6 H -0.3476 0.6211 0.1606 0.094 Uiso 1 1 calc R . . C14 C 0.3042(2) 0.5973(2) -0.02211(10) 0.0719(7) Uani 1 1 d . . . H14A H 0.3795 0.5282 -0.0090 0.086 Uiso 1 1 calc R . . H14B H 0.2444 0.5722 -0.0643 0.086 Uiso 1 1 calc R . . C5 C -0.2341(3) 0.5720(3) 0.24923(15) 0.0827(8) Uani 1 1 d . . . H5 H -0.3067 0.5161 0.2599 0.099 Uiso 1 1 calc R . . C13 C 0.3735(3) 0.7357(3) -0.02556(12) 0.0937(8) Uani 1 1 d . . . H13A H 0.3643 0.7633 -0.0709 0.112 Uiso 1 1 calc R . . H13B H 0.4773 0.7328 -0.0049 0.112 Uiso 1 1 calc R . . O2 O -0.08375(18) 0.52265(18) 0.35213(8) 0.0922(5) Uani 1 1 d . . . H2 H -0.0101 0.5517 0.3772 0.138 Uiso 1 1 calc R . . H11 H 0.0854(17) 0.7646(16) -0.0197(7) 0.041(5) Uiso 1 1 d . . . H18 H 0.2446(16) 0.8386(15) 0.1449(7) 0.033(5) Uiso 1 1 d . . . H15 H 0.1254(18) 0.5491(16) 0.0206(7) 0.049(5) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O3 0.0995(11) 0.0331(8) 0.0502(9) -0.0042(7) -0.0219(8) 0.0128(8) O5 0.0501(8) 0.0493(8) 0.0409(7) 0.0086(7) 0.0000(6) -0.0024(7) C1 0.0505(12) 0.0316(11) 0.0366(11) 0.0002(10) -0.0127(9) 0.0039(10) O1 0.0887(10) 0.0337(8) 0.0519(8) -0.0059(7) -0.0099(7) 0.0032(8) C10 0.0560(13) 0.0277(11) 0.0386(11) -0.0036(9) -0.0146(9) 0.0068(10) C17 0.0418(11) 0.0408(12) 0.0502(12) 0.0081(10) 0.0003(9) 0.0050(10) C18 0.0419(12) 0.0302(11) 0.0394(11) 0.0027(9) -0.0052(9) -0.0080(10) C2 0.0428(12) 0.0362(11) 0.0548(13) -0.0125(11) 0.0078(10) 0.0084(10) C11 0.0536(13) 0.0488(13) 0.0354(12) -0.0016(11) -0.0086(10) 0.0026(12) C19 0.0676(16) 0.0401(13) 0.0501(13) 0.0038(11) 0.0139(12) 0.0000(11) C3 0.0497(13) 0.0389(11) 0.0577(13) -0.0056(11) 0.0185(11) 0.0019(10) C9 0.0463(12) 0.0627(14) 0.0540(12) -0.0197(11) -0.0139(10) 0.0177(12) C15 0.0409(12) 0.0487(13) 0.0542(13) -0.0066(11) 0.0081(11) 0.0020(11) C20 0.0614(14) 0.0455(13) 0.0474(12) -0.0029(11) -0.0126(11) 0.0030(11) C16 0.0467(12) 0.0503(13) 0.0627(14) 0.0094(11) 0.0090(11) 0.0082(10) O4 0.0977(12) 0.1020(13) 0.0495(9) 0.0259(9) 0.0172(8) -0.0090(10) C8 0.0449(13) 0.0873(18) 0.0657(15) -0.0269(14) -0.0130(11) 0.0274(12) C4 0.0683(16) 0.0574(15) 0.0777(17) -0.0088(13) 0.0352(15) -0.0016(14) C7 0.0410(13) 0.0617(15) 0.0659(15) -0.0198(12) 0.0068(11) 0.0118(12) C21 0.0524(14) 0.0880(18) 0.0755(15) -0.0080(14) 0.0077(12) -0.0012(13) C12 0.0968(19) 0.0699(16) 0.0536(14) 0.0139(13) 0.0014(13) -0.0237(15) C6 0.0371(14) 0.098(2) 0.100(2) -0.0372(18) 0.0124(14) 0.0050(15) C14 0.0594(14) 0.0834(19) 0.0725(16) -0.0002(14) 0.0127(12) 0.0089(14) C5 0.0534(17) 0.084(2) 0.120(2) -0.0271(18) 0.0385(17) -0.0104(15) C13 0.0828(18) 0.122(2) 0.0808(18) -0.0078(18) 0.0272(15) -0.0182(19) O2 0.1067(14) 0.0888(13) 0.0958(13) 0.0085(11) 0.0546(11) -0.0195(11) _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 C10 1.4393(19) . ? O3 H3 0.8200 . ? O5 C19 1.322(2) . ? O5 C20 1.454(2) . ? C1 O1 1.216(2) . ? C1 C2 1.505(3) . ? C1 C18 1.515(2) . ? C10 C9 1.532(2) . ? C10 C11 1.536(2) . ? C10 C18 1.548(2) . ? C17 C16 1.521(2) . ? C17 C18 1.532(2) . ? C17 H17A 0.9700 . ? C17 H17B 0.9700 . ? C18 H18 0.920(15) . ? C2 C7 1.385(3) . ? C2 C3 1.414(2) . ? C11 C12 1.527(3) . ? C11 C15 1.529(3) . ? C11 H11 0.938(15) . ? C19 O4 1.216(2) . ? C19 C3 1.476(3) . ? C3 C4 1.404(3) . ? C9 C8 1.540(2) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C15 C16 1.520(2) . ? C15 C14 1.524(2) . ? C15 H15 0.977(16) . ? C20 C21 1.494(2) . ? C20 H20A 0.9700 . ? C20 H20B 0.9700 . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? C8 C7 1.502(3) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C4 O2 1.360(2) . ? C4 C5 1.387(3) . ? C7 C6 1.405(3) . ? C21 H21A 0.9600 . ? C21 H21B 0.9600 . ? C21 H21C 0.9600 . ? C12 C13 1.545(3) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C6 C5 1.362(3) . ? C6 H6 0.9300 . ? C14 C13 1.509(3) . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C5 H5 0.9300 . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? O2 H2 0.8200 . ? 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 C10 O3 H3 109.5 . . ? C19 O5 C20 117.42(15) . . ? O1 C1 C2 120.44(18) . . ? O1 C1 C18 122.51(18) . . ? C2 C1 C18 116.89(16) . . ? O3 C10 C9 106.19(15) . . ? O3 C10 C11 110.00(16) . . ? C9 C10 C11 109.15(14) . . ? O3 C10 C18 107.79(14) . . ? C9 C10 C18 113.33(15) . . ? C11 C10 C18 110.27(15) . . ? C16 C17 C18 111.40(15) . . ? C16 C17 H17A 109.3 . . ? C18 C17 H17A 109.3 . . ? C16 C17 H17B 109.3 . . ? C18 C17 H17B 109.3 . . ? H17A C17 H17B 108.0 . . ? C1 C18 C17 113.83(15) . . ? C1 C18 C10 111.61(15) . . ? C17 C18 C10 111.03(14) . . ? C1 C18 H18 104.1(9) . . ? C17 C18 H18 111.7(10) . . ? C10 C18 H18 104.0(9) . . ? C7 C2 C3 121.33(19) . . ? C7 C2 C1 115.12(18) . . ? C3 C2 C1 123.54(17) . . ? C12 C11 C15 103.25(17) . . ? C12 C11 C10 117.86(17) . . ? C15 C11 C10 115.42(16) . . ? C12 C11 H11 107.2(9) . . ? C15 C11 H11 108.2(10) . . ? C10 C11 H11 104.5(9) . . ? O4 C19 O5 122.7(2) . . ? O4 C19 C3 123.9(2) . . ? O5 C19 C3 113.35(18) . . ? C4 C3 C2 119.00(19) . . ? C4 C3 C19 117.7(2) . . ? C2 C3 C19 123.25(18) . . ? C10 C9 C8 116.74(15) . . ? C10 C9 H9A 108.1 . . ? C8 C9 H9A 108.1 . . ? C10 C9 H9B 108.1 . . ? C8 C9 H9B 108.1 . . ? H9A C9 H9B 107.3 . . ? C16 C15 C14 112.93(17) . . ? C16 C15 C11 110.55(16) . . ? C14 C15 C11 103.04(17) . . ? C16 C15 H15 108.4(9) . . ? C14 C15 H15 111.9(9) . . ? C11 C15 H15 109.9(10) . . ? O5 C20 C21 106.17(15) . . ? O5 C20 H20A 110.5 . . ? C21 C20 H20A 110.5 . . ? O5 C20 H20B 110.5 . . ? C21 C20 H20B 110.5 . . ? H20A C20 H20B 108.7 . . ? C15 C16 C17 112.12(15) . . ? C15 C16 H16A 109.2 . . ? C17 C16 H16A 109.2 . . ? C15 C16 H16B 109.2 . . ? C17 C16 H16B 109.2 . . ? H16A C16 H16B 107.9 . . ? C7 C8 C9 115.42(16) . . ? C7 C8 H8A 108.4 . . ? C9 C8 H8A 108.4 . . ? C7 C8 H8B 108.4 . . ? C9 C8 H8B 108.4 . . ? H8A C8 H8B 107.5 . . ? O2 C4 C5 118.0(2) . . ? O2 C4 C3 122.7(2) . . ? C5 C4 C3 119.3(2) . . ? C2 C7 C6 117.6(2) . . ? C2 C7 C8 121.2(2) . . ? C6 C7 C8 121.1(2) . . ? C20 C21 H21A 109.5 . . ? C20 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C20 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C11 C12 C13 104.11(18) . . ? C11 C12 H12A 110.9 . . ? C13 C12 H12A 110.9 . . ? C11 C12 H12B 110.9 . . ? C13 C12 H12B 110.9 . . ? H12A C12 H12B 109.0 . . ? C5 C6 C7 122.0(2) . . ? C5 C6 H6 119.0 . . ? C7 C6 H6 119.0 . . ? C13 C14 C15 105.33(18) . . ? C13 C14 H14A 110.7 . . ? C15 C14 H14A 110.7 . . ? C13 C14 H14B 110.7 . . ? C15 C14 H14B 110.7 . . ? H14A C14 H14B 108.8 . . ? C6 C5 C4 120.7(2) . . ? C6 C5 H5 119.6 . . ? C4 C5 H5 119.6 . . ? C14 C13 C12 107.36(18) . . ? C14 C13 H13A 110.2 . . ? C12 C13 H13A 110.2 . . ? C14 C13 H13B 110.2 . . ? C12 C13 H13B 110.2 . . ? H13A C13 H13B 108.5 . . ? C4 O2 H2 109.5 . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.229 _refine_diff_density_min -0.249 _refine_diff_density_rms 0.064