# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2009 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _publ_contact_author_name 'Junliang Zhang' _publ_contact_author_email JLZHANG@CHEM.ECNU.EDU.CN _publ_section_title ; Furans versus 4H-Pyrans: Catalyst-Controlled Regiodivergent Tandem Michael Addition/ Cyclization Reaction of 2-(1-Alkynyl)-2-alken-1-ones with 1,3-Dicarbonyl Compounds ; loop_ _publ_author_name 'Junliang Zhang' 'Yuanjing Xiao' # Attachment '4ca.cif' data_z _database_code_depnum_ccdc_archive 'CCDC 717871' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C24 H24 O4' _chemical_formula_weight 376.43 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 0.0016 '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)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 21.7484(4) _cell_length_b 8.3844(2) _cell_length_c 11.0805(2) _cell_angle_alpha 90.00 _cell_angle_beta 101.2150(10) _cell_angle_gamma 90.00 _cell_volume 1981.92(7) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.452 _exptl_crystal_size_mid 0.266 _exptl_crystal_size_min 0.242 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.262 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 800 _exptl_absorpt_coefficient_mu 0.085 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.820104 _exptl_absorpt_correction_T_max 1 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 17045 _diffrn_reflns_av_R_equivalents 0.0230 _diffrn_reflns_av_sigmaI/netI 0.0201 _diffrn_reflns_limit_h_min -25 _diffrn_reflns_limit_h_max 25 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 1.91 _diffrn_reflns_theta_max 25.01 _reflns_number_total 3476 _reflns_number_gt 3025 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0419P)^2^+0.7672P] 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 SHELXL _refine_ls_extinction_coef 0.0030(9) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3476 _refine_ls_number_parameters 254 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0426 _refine_ls_R_factor_gt 0.0366 _refine_ls_wR_factor_ref 0.0985 _refine_ls_wR_factor_gt 0.0935 _refine_ls_goodness_of_fit_ref 1.039 _refine_ls_restrained_S_all 1.039 _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 O1 O 0.25002(5) 0.79870(14) 0.64727(10) 0.0489(3) Uani 1 1 d . . . O2 O 0.10031(5) 0.81600(13) 0.51262(11) 0.0477(3) Uani 1 1 d . . . O3 O 0.57638(5) 0.29713(14) 0.35366(11) 0.0504(3) Uani 1 1 d . . . O4 O 0.32019(5) 0.29542(11) 0.54762(9) 0.0376(3) Uani 1 1 d . . . C1 C 0.12657(6) 0.48648(15) 0.40231(12) 0.0297(3) Uani 1 1 d . . . C2 C 0.12053(7) 0.47997(18) 0.27560(13) 0.0381(3) Uani 1 1 d . . . H2A H 0.1512 0.5298 0.2377 0.046 Uiso 1 1 calc R . . C3 C 0.07039(8) 0.4017(2) 0.20342(15) 0.0460(4) Uani 1 1 d . . . H3A H 0.0667 0.3990 0.1166 0.055 Uiso 1 1 calc R . . C4 C 0.02590(7) 0.32802(19) 0.25696(16) 0.0456(4) Uani 1 1 d . . . H4A H -0.0077 0.2713 0.2076 0.055 Uiso 1 1 calc R . . C5 C 0.03028(7) 0.33685(19) 0.38251(16) 0.0457(4) Uani 1 1 d . . . H5A H -0.0009 0.2886 0.4197 0.055 Uiso 1 1 calc R . . C6 C 0.08013(7) 0.41601(18) 0.45445(14) 0.0381(3) Uani 1 1 d . . . H6A H 0.0826 0.4223 0.5409 0.046 Uiso 1 1 calc R . . C7 C 0.39631(6) 0.35737(16) 0.42218(12) 0.0318(3) Uani 1 1 d . . . C8 C 0.41727(7) 0.45511(18) 0.33781(14) 0.0393(4) Uani 1 1 d . . . H8A H 0.3902 0.5356 0.2971 0.047 Uiso 1 1 calc R . . C9 C 0.47659(7) 0.43885(18) 0.31109(14) 0.0409(4) Uani 1 1 d . . . H9A H 0.4899 0.5075 0.2529 0.049 Uiso 1 1 calc R . . C10 C 0.51625(7) 0.32195(18) 0.36982(14) 0.0376(3) Uani 1 1 d . . . C11 C 0.49548(7) 0.22073(19) 0.45167(15) 0.0436(4) Uani 1 1 d . . . H11A H 0.5222 0.1381 0.4900 0.052 Uiso 1 1 calc R . . C12 C 0.43653(7) 0.23783(18) 0.47859(14) 0.0400(4) Uani 1 1 d . . . H12A H 0.4232 0.1678 0.5359 0.048 Uiso 1 1 calc R . . C13 C 0.26308(7) 0.34970(17) 0.56732(14) 0.0363(3) Uani 1 1 d . . . C14 C 0.24228(6) 0.46964(16) 0.48887(12) 0.0295(3) Uani 1 1 d . . . C15 C 0.28880(6) 0.49135(16) 0.41509(12) 0.0306(3) Uani 1 1 d . . . H15A H 0.2873 0.5663 0.3503 0.037 Uiso 1 1 calc R . . C16 C 0.33533(6) 0.38565(16) 0.45441(12) 0.0308(3) Uani 1 1 d . . . C17 C 0.23800(9) 0.2694(2) 0.66646(18) 0.0588(5) Uani 1 1 d . . . H17A H 0.1975 0.3167 0.6726 0.088 Uiso 1 1 calc R . . H17B H 0.2675 0.2828 0.7448 0.088 Uiso 1 1 calc R . . H17C H 0.2324 0.1555 0.6476 0.088 Uiso 1 1 calc R . . C18 C 0.18267(6) 0.56458(15) 0.48427(12) 0.0291(3) Uani 1 1 d . . . H18A H 0.1740 0.5680 0.5696 0.035 Uiso 1 1 calc R . . C19 C 0.19355(6) 0.73706(16) 0.44604(12) 0.0308(3) Uani 1 1 d . . . H19A H 0.2042 0.7368 0.3622 0.037 Uiso 1 1 calc R . . C20 C 0.13599(7) 0.84235(17) 0.44472(14) 0.0354(3) Uani 1 1 d . . . C21 C 0.12764(9) 0.9790(2) 0.3570(2) 0.0659(6) Uani 1 1 d . . . H21A H 0.0897 1.0383 0.3643 0.099 Uiso 1 1 calc R . . H21B H 0.1237 0.9388 0.2728 0.099 Uiso 1 1 calc R . . H21C H 0.1641 1.0499 0.3762 0.099 Uiso 1 1 calc R . . C22 C 0.24774(7) 0.81257(16) 0.53786(14) 0.0363(3) Uani 1 1 d . . . C23 C 0.29657(8) 0.9025(2) 0.48767(18) 0.0554(5) Uani 1 1 d . . . H23A H 0.3280 0.9445 0.5558 0.083 Uiso 1 1 calc R . . H23B H 0.2768 0.9912 0.4367 0.083 Uiso 1 1 calc R . . H23C H 0.3169 0.8309 0.4375 0.083 Uiso 1 1 calc R . . C24 C 0.60108(8) 0.4056(2) 0.27686(16) 0.0533(4) Uani 1 1 d . . . H24A H 0.6441 0.3747 0.2729 0.080 Uiso 1 1 calc R . . H24B H 0.6010 0.5135 0.3107 0.080 Uiso 1 1 calc R . . H24C H 0.5752 0.4033 0.1940 0.080 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 0.0493(7) 0.0522(7) 0.0425(7) -0.0139(5) 0.0024(5) -0.0018(5) O2 0.0422(6) 0.0472(6) 0.0571(7) -0.0054(5) 0.0182(5) 0.0066(5) O3 0.0332(6) 0.0595(7) 0.0592(7) 0.0000(6) 0.0102(5) 0.0071(5) O4 0.0369(6) 0.0327(5) 0.0432(6) 0.0081(4) 0.0075(4) 0.0061(4) C1 0.0292(7) 0.0251(6) 0.0350(7) -0.0001(6) 0.0063(6) 0.0046(5) C2 0.0385(8) 0.0405(8) 0.0361(8) -0.0030(6) 0.0092(6) -0.0037(6) C3 0.0484(9) 0.0484(9) 0.0375(8) -0.0055(7) -0.0005(7) -0.0012(8) C4 0.0356(8) 0.0388(8) 0.0563(10) -0.0039(7) -0.0060(7) -0.0002(7) C5 0.0320(8) 0.0421(9) 0.0636(11) 0.0045(8) 0.0109(7) -0.0035(7) C6 0.0374(8) 0.0390(8) 0.0394(8) 0.0019(6) 0.0114(6) 0.0000(6) C7 0.0319(7) 0.0282(7) 0.0331(7) -0.0056(6) 0.0007(6) 0.0012(6) C8 0.0367(8) 0.0355(8) 0.0451(8) 0.0056(7) 0.0066(7) 0.0077(6) C9 0.0402(8) 0.0397(8) 0.0436(9) 0.0025(7) 0.0102(7) 0.0014(7) C10 0.0302(7) 0.0401(8) 0.0405(8) -0.0094(6) 0.0024(6) 0.0019(6) C11 0.0365(8) 0.0422(8) 0.0497(9) 0.0054(7) 0.0027(7) 0.0116(7) C12 0.0392(8) 0.0361(8) 0.0436(8) 0.0055(7) 0.0050(7) 0.0054(6) C13 0.0356(8) 0.0325(7) 0.0409(8) 0.0039(6) 0.0081(6) 0.0027(6) C14 0.0319(7) 0.0269(7) 0.0284(7) -0.0033(5) 0.0024(5) -0.0014(5) C15 0.0341(7) 0.0272(7) 0.0295(7) 0.0004(5) 0.0037(6) 0.0019(6) C16 0.0343(7) 0.0267(7) 0.0299(7) -0.0020(5) 0.0029(6) -0.0010(6) C17 0.0593(11) 0.0563(11) 0.0664(12) 0.0285(9) 0.0260(9) 0.0155(9) C18 0.0317(7) 0.0288(7) 0.0275(7) -0.0002(5) 0.0074(5) 0.0009(5) C19 0.0335(7) 0.0284(7) 0.0313(7) -0.0007(6) 0.0083(6) 0.0011(6) C20 0.0313(7) 0.0317(7) 0.0416(8) -0.0043(6) 0.0031(6) 0.0006(6) C21 0.0525(11) 0.0541(11) 0.0914(15) 0.0296(10) 0.0147(10) 0.0169(9) C22 0.0343(8) 0.0277(7) 0.0466(9) -0.0064(6) 0.0068(6) 0.0044(6) C23 0.0440(10) 0.0449(9) 0.0768(13) -0.0018(9) 0.0108(9) -0.0088(8) C24 0.0368(9) 0.0738(12) 0.0501(10) -0.0044(9) 0.0107(7) -0.0015(8) _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 C22 1.2093(18) . ? O2 C20 1.2016(18) . ? O3 C10 1.3699(18) . ? O3 C24 1.420(2) . ? O4 C16 1.3710(17) . ? O4 C13 1.3795(17) . ? C1 C2 1.386(2) . ? C1 C6 1.3891(19) . ? C1 C18 1.5204(19) . ? C2 C3 1.386(2) . ? C2 H2A 0.9500 . ? C3 C4 1.376(2) . ? C3 H3A 0.9500 . ? C4 C5 1.378(2) . ? C4 H4A 0.9500 . ? C5 C6 1.384(2) . ? C5 H5A 0.9500 . ? C6 H6A 0.9500 . ? C7 C8 1.385(2) . ? C7 C12 1.396(2) . ? C7 C16 1.4585(19) . ? C8 C9 1.385(2) . ? C8 H8A 0.9500 . ? C9 C10 1.382(2) . ? C9 H9A 0.9500 . ? C10 C11 1.381(2) . ? C11 C12 1.379(2) . ? C11 H11A 0.9500 . ? C12 H12A 0.9500 . ? C13 C14 1.349(2) . ? C13 C17 1.480(2) . ? C14 C15 1.4305(19) . ? C14 C18 1.5137(18) . ? C15 C16 1.3519(19) . ? C15 H15A 0.9500 . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C18 C19 1.5381(19) . ? C18 H18A 1.0000 . ? C19 C20 1.5295(19) . ? C19 C22 1.536(2) . ? C19 H19A 1.0000 . ? C20 C21 1.491(2) . ? C21 H21A 0.9800 . ? C21 H21B 0.9800 . ? C21 H21C 0.9800 . ? C22 C23 1.495(2) . ? C23 H23A 0.9800 . ? C23 H23B 0.9800 . ? C23 H23C 0.9800 . ? C24 H24A 0.9800 . ? C24 H24B 0.9800 . ? C24 H24C 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 C10 O3 C24 117.58(13) . . ? C16 O4 C13 107.02(10) . . ? C2 C1 C6 118.12(13) . . ? C2 C1 C18 121.94(12) . . ? C6 C1 C18 119.92(12) . . ? C1 C2 C3 120.82(14) . . ? C1 C2 H2A 119.6 . . ? C3 C2 H2A 119.6 . . ? C4 C3 C2 120.29(15) . . ? C4 C3 H3A 119.9 . . ? C2 C3 H3A 119.9 . . ? C3 C4 C5 119.66(14) . . ? C3 C4 H4A 120.2 . . ? C5 C4 H4A 120.2 . . ? C4 C5 C6 119.99(15) . . ? C4 C5 H5A 120.0 . . ? C6 C5 H5A 120.0 . . ? C5 C6 C1 121.06(14) . . ? C5 C6 H6A 119.5 . . ? C1 C6 H6A 119.5 . . ? C8 C7 C12 117.85(13) . . ? C8 C7 C16 120.22(12) . . ? C12 C7 C16 121.85(13) . . ? C7 C8 C9 121.90(14) . . ? C7 C8 H8A 119.1 . . ? C9 C8 H8A 119.1 . . ? C10 C9 C8 119.41(14) . . ? C10 C9 H9A 120.3 . . ? C8 C9 H9A 120.3 . . ? O3 C10 C11 115.79(13) . . ? O3 C10 C9 124.78(14) . . ? C11 C10 C9 119.43(14) . . ? C12 C11 C10 120.99(14) . . ? C12 C11 H11A 119.5 . . ? C10 C11 H11A 119.5 . . ? C11 C12 C7 120.39(14) . . ? C11 C12 H12A 119.8 . . ? C7 C12 H12A 119.8 . . ? C14 C13 O4 110.08(12) . . ? C14 C13 C17 133.78(14) . . ? O4 C13 C17 116.14(13) . . ? C13 C14 C15 106.11(12) . . ? C13 C14 C18 126.26(12) . . ? C15 C14 C18 127.59(12) . . ? C16 C15 C14 107.49(12) . . ? C16 C15 H15A 126.3 . . ? C14 C15 H15A 126.3 . . ? C15 C16 O4 109.28(12) . . ? C15 C16 C7 133.39(13) . . ? O4 C16 C7 117.25(11) . . ? C13 C17 H17A 109.5 . . ? C13 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C13 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C14 C18 C1 112.10(11) . . ? C14 C18 C19 109.09(11) . . ? C1 C18 C19 112.90(11) . . ? C14 C18 H18A 107.5 . . ? C1 C18 H18A 107.5 . . ? C19 C18 H18A 107.5 . . ? C20 C19 C22 106.84(11) . . ? C20 C19 C18 112.08(11) . . ? C22 C19 C18 110.15(11) . . ? C20 C19 H19A 109.2 . . ? C22 C19 H19A 109.2 . . ? C18 C19 H19A 109.2 . . ? O2 C20 C21 122.55(14) . . ? O2 C20 C19 120.99(13) . . ? C21 C20 C19 116.46(13) . . ? 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 . . ? O1 C22 C23 121.86(14) . . ? O1 C22 C19 120.07(13) . . ? C23 C22 C19 118.07(13) . . ? C22 C23 H23A 109.5 . . ? C22 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C22 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? O3 C24 H24A 109.5 . . ? O3 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? O3 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 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 -1.6(2) . . . . ? C18 C1 C2 C3 177.03(13) . . . . ? C1 C2 C3 C4 -0.5(2) . . . . ? C2 C3 C4 C5 2.2(2) . . . . ? C3 C4 C5 C6 -1.7(2) . . . . ? C4 C5 C6 C1 -0.5(2) . . . . ? C2 C1 C6 C5 2.1(2) . . . . ? C18 C1 C6 C5 -176.58(13) . . . . ? C12 C7 C8 C9 -1.4(2) . . . . ? C16 C7 C8 C9 175.54(14) . . . . ? C7 C8 C9 C10 0.1(2) . . . . ? C24 O3 C10 C11 -175.71(14) . . . . ? C24 O3 C10 C9 4.1(2) . . . . ? C8 C9 C10 O3 -178.13(14) . . . . ? C8 C9 C10 C11 1.7(2) . . . . ? O3 C10 C11 C12 177.75(14) . . . . ? C9 C10 C11 C12 -2.1(2) . . . . ? C10 C11 C12 C7 0.7(2) . . . . ? C8 C7 C12 C11 1.0(2) . . . . ? C16 C7 C12 C11 -175.88(14) . . . . ? C16 O4 C13 C14 0.41(16) . . . . ? C16 O4 C13 C17 -179.18(14) . . . . ? O4 C13 C14 C15 0.38(16) . . . . ? C17 C13 C14 C15 179.87(18) . . . . ? O4 C13 C14 C18 -177.70(12) . . . . ? C17 C13 C14 C18 1.8(3) . . . . ? C13 C14 C15 C16 -1.04(15) . . . . ? C18 C14 C15 C16 177.00(13) . . . . ? C14 C15 C16 O4 1.31(15) . . . . ? C14 C15 C16 C7 -175.13(14) . . . . ? C13 O4 C16 C15 -1.08(15) . . . . ? C13 O4 C16 C7 176.01(12) . . . . ? C8 C7 C16 C15 2.8(2) . . . . ? C12 C7 C16 C15 179.65(15) . . . . ? C8 C7 C16 O4 -173.38(12) . . . . ? C12 C7 C16 O4 3.43(19) . . . . ? C13 C14 C18 C1 -87.76(17) . . . . ? C15 C14 C18 C1 94.57(16) . . . . ? C13 C14 C18 C19 146.44(14) . . . . ? C15 C14 C18 C19 -31.23(18) . . . . ? C2 C1 C18 C14 -69.61(16) . . . . ? C6 C1 C18 C14 109.03(14) . . . . ? C2 C1 C18 C19 54.09(17) . . . . ? C6 C1 C18 C19 -127.28(13) . . . . ? C14 C18 C19 C20 -177.56(11) . . . . ? C1 C18 C19 C20 57.10(15) . . . . ? C14 C18 C19 C22 -58.76(14) . . . . ? C1 C18 C19 C22 175.90(11) . . . . ? C22 C19 C20 O2 -91.23(16) . . . . ? C18 C19 C20 O2 29.51(19) . . . . ? C22 C19 C20 C21 87.77(17) . . . . ? C18 C19 C20 C21 -151.49(15) . . . . ? C20 C19 C22 O1 75.59(16) . . . . ? C18 C19 C22 O1 -46.37(17) . . . . ? C20 C19 C22 C23 -104.27(15) . . . . ? C18 C19 C22 C23 133.77(13) . . . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 25.01 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.236 _refine_diff_density_min -0.161 _refine_diff_density_rms 0.032