#------------------------------------------------------------------------------ #$Date: 2014-07-11 17:35:18 +0300 (Fri, 11 Jul 2014) $ #$Revision: 120071 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/50/65/1506583.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/ # # All data on this site have been placed in the public domain by the # contributors. # data_1506583 loop_ _publ_author_name 'Grecian, Scott' 'Wrobleski, Aaron D.' 'Aub\'e, Jeffrey' _publ_section_title ; Regioselective single and double conjugate additions to substituted cyclohexa-2,5-dienone monoacetals. ; _journal_issue 15 _journal_name_full 'Organic letters' _journal_page_first 3167 _journal_page_last 3170 _journal_volume 7 _journal_year 2005 _chemical_formula_moiety 'C23 H29 N O7' _chemical_formula_sum 'C23 H29 N O7' _chemical_formula_weight 431.47 _chemical_name_systematic ; Ethyl 9,9-diethoxy-3,7-dioxo-5- (phenylcarbamoyl)bicyclo[3.3.1]nonane-2-carboxylate ; _space_group_IT_number 14 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2yn' _symmetry_space_group_name_H-M 'P 1 21/n 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-97 _cell_angle_alpha 90.00 _cell_angle_beta 108.088(3) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 10.5188(12) _cell_length_b 14.2466(16) _cell_length_c 14.9179(16) _cell_measurement_reflns_used 8679 _cell_measurement_temperature 100(2) _cell_measurement_theta_max 26.00 _cell_measurement_theta_min 2.49 _cell_volume 2125.1(4) _computing_cell_refinement 'Bruker SMART' _computing_data_collection 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_molecular_graphics 'SHELXTL (Sheldrick, 2000)' _computing_publication_material 'SHELXTL (Sheldrick, 2000)' _computing_structure_refinement 'SHELXTL (Sheldrick, 2000)' _computing_structure_solution 'SHELXTL (Sheldrick, 2000)' _diffrn_ambient_temperature 100(2) _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method '\w scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0202 _diffrn_reflns_av_sigmaI/netI 0.0219 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_number 13141 _diffrn_reflns_theta_full 26.00 _diffrn_reflns_theta_max 26.00 _diffrn_reflns_theta_min 2.10 _diffrn_standards_decay_% -0.50 _diffrn_standards_number 314 _exptl_absorpt_coefficient_mu 0.100 _exptl_absorpt_correction_T_max 0.971 _exptl_absorpt_correction_T_min 0.946 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS (Sheldrick, 2002)' _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.349 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 920 _exptl_crystal_size_max 0.54 _exptl_crystal_size_mid 0.45 _exptl_crystal_size_min 0.30 _refine_diff_density_max 0.382 _refine_diff_density_min -0.220 _refine_diff_density_rms 0.042 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.040 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 280 _refine_ls_number_reflns 4169 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.040 _refine_ls_R_factor_all 0.0383 _refine_ls_R_factor_gt 0.0353 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0500P)^2^+0.8400P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0943 _refine_ls_wR_factor_ref 0.0968 _reflns_number_gt 3808 _reflns_number_total 4169 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file ol050715csi20050404_121828.cif _[local]_cod_data_source_block compound_17_ _[local]_cod_cif_authors_sg_H-M 'P 21/n' _cod_database_code 1506583 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' 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 C1 C 0.36309(11) 0.16572(8) 0.06978(8) 0.0156(2) Uani 1 1 d . C2 C 0.36990(12) 0.27193(8) 0.09246(8) 0.0175(2) Uani 1 1 d . H2A H 0.4368 0.2820 0.1550 0.021 Uiso 1 1 calc R H2B H 0.4016 0.3054 0.0453 0.021 Uiso 1 1 calc R C3 C 0.24020(12) 0.31430(8) 0.09304(8) 0.0171(2) Uani 1 1 d . C4 C 0.13125(12) 0.26328(8) 0.09316(8) 0.0160(2) Uani 1 1 d . C5 C 0.13041(11) 0.15750(8) 0.08319(8) 0.0153(2) Uani 1 1 d . H5 H 0.0746 0.1303 0.1202 0.018 Uiso 1 1 calc R C6 C 0.06805(12) 0.12921(8) -0.02118(8) 0.0173(2) Uani 1 1 d . H6A H 0.0636 0.0600 -0.0268 0.021 Uiso 1 1 calc R H6B H -0.0240 0.1543 -0.0458 0.021 Uiso 1 1 calc R C7 C 0.15253(12) 0.16800(8) -0.07761(8) 0.0178(2) Uani 1 1 d . C8 C 0.30135(12) 0.14895(9) -0.03756(8) 0.0184(3) Uani 1 1 d . H8A H 0.3486 0.1893 -0.0710 0.022 Uiso 1 1 calc R H8B H 0.3180 0.0829 -0.0513 0.022 Uiso 1 1 calc R C9 C 0.27312(11) 0.11785(8) 0.12255(8) 0.0152(2) Uani 1 1 d . C10 C 0.50941(11) 0.12975(8) 0.09738(8) 0.0160(2) Uani 1 1 d . O11 O 0.55936(9) 0.10674(7) 0.03719(6) 0.0224(2) Uani 1 1 d . N12 N 0.57692(10) 0.13059(7) 0.19138(7) 0.0177(2) Uani 1 1 d . H12 H 0.5289 0.1500 0.2312 0.021 Uiso 1 1 d R C13 C 0.70456(12) 0.09242(8) 0.23726(8) 0.0177(2) Uani 1 1 d . C14 C 0.73943(13) 0.08251(9) 0.33508(9) 0.0217(3) Uani 1 1 d . H14 H 0.6779 0.1005 0.3670 0.026 Uiso 1 1 calc R C15 C 0.86317(14) 0.04657(10) 0.38575(9) 0.0257(3) Uani 1 1 d . H15 H 0.8862 0.0403 0.4523 0.031 Uiso 1 1 calc R C16 C 0.95401(13) 0.01962(9) 0.33982(10) 0.0260(3) Uani 1 1 d . H16 H 1.0392 -0.0045 0.3746 0.031 Uiso 1 1 calc R C17 C 0.91841(12) 0.02852(9) 0.24270(9) 0.0230(3) Uani 1 1 d . H17 H 0.9796 0.0092 0.2110 0.028 Uiso 1 1 calc R C18 C 0.79495(12) 0.06507(9) 0.19055(9) 0.0196(3) Uani 1 1 d . H18 H 0.7724 0.0714 0.1240 0.024 Uiso 1 1 calc R O19 O 0.24529(9) 0.40819(6) 0.09707(6) 0.0219(2) Uani 1 1 d . H19 H 0.1729 0.4291 0.1017 0.026 Uiso 1 1 calc R C20 C 0.01404(12) 0.31344(9) 0.10084(7) 0.0163(2) Uani 1 1 d . O21 O 0.00833(8) 0.39944(6) 0.10769(6) 0.0200(2) Uani 1 1 d . O22 O -0.08766(8) 0.25705(6) 0.09995(6) 0.01874(19) Uani 1 1 d . C23 C -0.20665(12) 0.30196(9) 0.11177(9) 0.0206(3) Uani 1 1 d . H23A H -0.2847 0.2600 0.0869 0.025 Uiso 1 1 calc R H23B H -0.2250 0.3610 0.0749 0.025 Uiso 1 1 calc R C24 C -0.18863(13) 0.32344(10) 0.21402(9) 0.0240(3) Uani 1 1 d . H24A H -0.2745 0.3428 0.2210 0.036 Uiso 1 1 d R H24B H -0.1234 0.3743 0.2353 0.036 Uiso 1 1 d R H24C H -0.1563 0.2672 0.2522 0.036 Uiso 1 1 d R O25 O 0.10468(9) 0.20942(7) -0.15139(6) 0.0235(2) Uani 1 1 d . O26 O 0.33223(8) 0.14069(6) 0.21877(5) 0.01607(19) Uani 1 1 d . C27 C 0.25974(12) 0.11324(9) 0.28196(8) 0.0190(3) Uani 1 1 d . H27A H 0.2292 0.0474 0.2700 0.023 Uiso 1 1 calc R H27B H 0.1805 0.1539 0.2730 0.023 Uiso 1 1 calc R C28 C 0.35455(13) 0.12362(9) 0.38077(8) 0.0225(3) Uani 1 1 d . H28A H 0.3076 0.1085 0.4263 0.034 Uiso 1 1 d R H28B H 0.3873 0.1884 0.3906 0.034 Uiso 1 1 d R H28C H 0.4303 0.0807 0.3896 0.034 Uiso 1 1 d R O29 O 0.25635(8) 0.02033(6) 0.10769(5) 0.01653(19) Uani 1 1 d . C30 C 0.36949(12) -0.04050(8) 0.14765(8) 0.0180(2) Uani 1 1 d . H30A H 0.4155 -0.0233 0.2141 0.022 Uiso 1 1 calc R H30B H 0.4341 -0.0353 0.1118 0.022 Uiso 1 1 calc R C31 C 0.31507(13) -0.13902(9) 0.14160(10) 0.0240(3) Uani 1 1 d . H31A H 0.3889 -0.1831 0.1675 0.036 Uiso 1 1 d R H31B H 0.2690 -0.1548 0.0755 0.036 Uiso 1 1 d R H31C H 0.2519 -0.1432 0.1779 0.036 Uiso 1 1 d R loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0150(6) 0.0170(6) 0.0154(5) 0.0002(4) 0.0057(4) -0.0003(4) C2 0.0163(6) 0.0168(6) 0.0208(6) 0.0007(4) 0.0076(5) -0.0013(5) C3 0.0191(6) 0.0161(6) 0.0160(5) -0.0002(4) 0.0054(4) 0.0001(5) C4 0.0166(6) 0.0173(6) 0.0143(5) 0.0003(4) 0.0050(4) 0.0006(5) C5 0.0152(6) 0.0157(6) 0.0159(5) 0.0011(4) 0.0061(4) -0.0005(4) C6 0.0159(6) 0.0170(6) 0.0177(5) -0.0004(4) 0.0033(4) -0.0011(5) C7 0.0207(6) 0.0161(6) 0.0162(5) -0.0030(4) 0.0051(5) -0.0007(5) C8 0.0175(6) 0.0239(6) 0.0152(5) 0.0004(5) 0.0068(5) -0.0009(5) C9 0.0164(6) 0.0154(6) 0.0144(5) 0.0000(4) 0.0055(4) -0.0004(4) C10 0.0161(6) 0.0141(6) 0.0186(6) -0.0006(4) 0.0064(5) -0.0023(4) O11 0.0188(4) 0.0310(5) 0.0194(4) -0.0032(4) 0.0088(3) 0.0014(4) N12 0.0150(5) 0.0210(5) 0.0177(5) -0.0020(4) 0.0059(4) 0.0021(4) C13 0.0159(6) 0.0140(6) 0.0219(6) -0.0017(4) 0.0042(5) -0.0013(4) C14 0.0216(6) 0.0215(6) 0.0220(6) -0.0027(5) 0.0069(5) 0.0020(5) C15 0.0265(7) 0.0249(7) 0.0220(6) -0.0005(5) 0.0022(5) 0.0042(5) C16 0.0186(6) 0.0235(7) 0.0315(7) 0.0004(5) 0.0016(5) 0.0045(5) C17 0.0178(6) 0.0201(6) 0.0323(7) -0.0020(5) 0.0096(5) 0.0006(5) C18 0.0182(6) 0.0173(6) 0.0235(6) -0.0010(5) 0.0066(5) -0.0020(5) O19 0.0186(4) 0.0154(4) 0.0335(5) -0.0023(4) 0.0106(4) -0.0007(3) C20 0.0173(6) 0.0194(6) 0.0122(5) 0.0000(4) 0.0046(4) -0.0009(5) O21 0.0202(4) 0.0172(4) 0.0235(4) -0.0013(3) 0.0082(3) 0.0008(3) O22 0.0157(4) 0.0188(4) 0.0238(4) -0.0005(3) 0.0092(3) 0.0000(3) C23 0.0155(6) 0.0233(6) 0.0256(6) 0.0003(5) 0.0099(5) 0.0018(5) C24 0.0249(7) 0.0241(7) 0.0267(6) -0.0018(5) 0.0136(5) -0.0012(5) O25 0.0244(5) 0.0278(5) 0.0177(4) 0.0037(4) 0.0057(4) 0.0027(4) O26 0.0164(4) 0.0189(4) 0.0140(4) -0.0006(3) 0.0062(3) -0.0014(3) C27 0.0203(6) 0.0214(6) 0.0178(6) 0.0004(5) 0.0096(5) -0.0011(5) C28 0.0282(7) 0.0227(6) 0.0171(6) -0.0007(5) 0.0079(5) -0.0028(5) O29 0.0160(4) 0.0145(4) 0.0183(4) 0.0005(3) 0.0042(3) 0.0008(3) C30 0.0172(6) 0.0173(6) 0.0192(5) 0.0011(4) 0.0055(4) 0.0024(5) C31 0.0210(6) 0.0183(6) 0.0315(7) 0.0027(5) 0.0064(5) 0.0012(5) 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' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle C2 C1 C8 110.68(9) C2 C1 C10 106.87(9) C8 C1 C10 106.65(9) C2 C1 C9 108.10(9) C8 C1 C9 109.17(9) C10 C1 C9 115.35(9) C3 C2 C1 114.58(10) C3 C2 H2A 108.6 C1 C2 H2A 108.6 C3 C2 H2B 108.6 C1 C2 H2B 108.6 H2A C2 H2B 107.6 O19 C3 C4 123.83(11) O19 C3 C2 112.32(10) C4 C3 C2 123.81(11) C3 C4 C20 118.15(11) C3 C4 C5 120.80(11) C20 C4 C5 121.03(10) C4 C5 C9 110.64(9) C4 C5 C6 110.28(9) C9 C5 C6 110.34(9) C4 C5 H5 108.5 C9 C5 H5 108.5 C6 C5 H5 108.5 C7 C6 C5 109.16(9) C7 C6 H6A 109.8 C5 C6 H6A 109.8 C7 C6 H6B 109.8 C5 C6 H6B 109.8 H6A C6 H6B 108.3 O25 C7 C6 122.38(11) O25 C7 C8 122.11(11) C6 C7 C8 115.48(10) C7 C8 C1 115.46(9) C7 C8 H8A 108.4 C1 C8 H8A 108.4 C7 C8 H8B 108.4 C1 C8 H8B 108.4 H8A C8 H8B 107.5 O29 C9 O26 112.38(9) O29 C9 C5 104.01(9) O26 C9 C5 111.85(9) O29 C9 C1 114.63(9) O26 C9 C1 105.47(9) C5 C9 C1 108.60(9) O11 C10 N12 123.74(11) O11 C10 C1 120.85(10) N12 C10 C1 115.33(10) C10 N12 C13 127.52(10) C10 N12 H12 116.5 C13 N12 H12 115.2 C14 C13 C18 119.61(11) C14 C13 N12 116.54(10) C18 C13 N12 123.85(11) C15 C14 C13 120.34(12) C15 C14 H14 119.8 C13 C14 H14 119.8 C14 C15 C16 120.40(12) C14 C15 H15 119.8 C16 C15 H15 119.8 C17 C16 C15 119.07(12) C17 C16 H16 120.5 C15 C16 H16 120.5 C16 C17 C18 121.43(12) C16 C17 H17 119.3 C18 C17 H17 119.3 C17 C18 C13 119.14(12) C17 C18 H18 120.4 C13 C18 H18 120.4 C3 O19 H19 109.5 O21 C20 O22 122.66(11) O21 C20 C4 123.86(11) O22 C20 C4 113.48(10) C20 O22 C23 116.63(9) O22 C23 C24 111.50(10) O22 C23 H23A 109.3 C24 C23 H23A 109.3 O22 C23 H23B 109.3 C24 C23 H23B 109.3 H23A C23 H23B 108.0 C23 C24 H24A 109.5 C23 C24 H24B 109.5 H24A C24 H24B 109.5 C23 C24 H24C 109.5 H24A C24 H24C 109.5 H24B C24 H24C 109.5 C9 O26 C27 116.57(9) O26 C27 C28 106.83(10) O26 C27 H27A 110.4 C28 C27 H27A 110.4 O26 C27 H27B 110.4 C28 C27 H27B 110.4 H27A C27 H27B 108.6 C27 C28 H28A 109.5 C27 C28 H28B 109.5 H28A C28 H28B 109.5 C27 C28 H28C 109.5 H28A C28 H28C 109.5 H28B C28 H28C 109.5 C9 O29 C30 118.70(9) O29 C30 C31 106.57(10) O29 C30 H30A 110.4 C31 C30 H30A 110.4 O29 C30 H30B 110.4 C31 C30 H30B 110.4 H30A C30 H30B 108.6 C30 C31 H31A 109.5 C30 C31 H31B 109.5 H31A C31 H31B 109.5 C30 C31 H31C 109.5 H31A C31 H31C 109.5 H31B C31 H31C 109.5 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance C1 C2 1.5474(16) C1 C8 1.5483(15) C1 C10 1.5515(16) C1 C9 1.5630(15) C2 C3 1.4943(16) C2 H2A 0.9900 C2 H2B 0.9900 C3 O19 1.3394(15) C3 C4 1.3575(17) C4 C20 1.4601(16) C4 C5 1.5140(16) C5 C9 1.5395(16) C5 C6 1.5436(15) C5 H5 1.0000 C6 C7 1.5061(16) C6 H6A 0.9900 C6 H6B 0.9900 C7 O25 1.2121(15) C7 C8 1.5167(17) C8 H8A 0.9900 C8 H8B 0.9900 C9 O29 1.4093(14) C9 O26 1.4138(13) C10 O11 1.2177(14) C10 N12 1.3610(15) N12 C13 1.4129(15) N12 H12 0.9330 C13 C14 1.3971(17) C13 C18 1.3974(17) C14 C15 1.3845(18) C14 H14 0.9500 C15 C16 1.3916(19) C15 H15 0.9500 C16 C17 1.3851(19) C16 H16 0.9500 C17 C18 1.3913(18) C17 H17 0.9500 C18 H18 0.9500 O19 H19 0.8400 C20 O21 1.2325(15) C20 O22 1.3346(15) O22 C23 1.4642(14) C23 C24 1.5089(17) C23 H23A 0.9900 C23 H23B 0.9900 C24 H24A 0.9800 C24 H24B 0.9800 C24 H24C 0.9800 O26 C27 1.4386(14) C27 C28 1.5087(16) C27 H27A 0.9900 C27 H27B 0.9900 C28 H28A 0.9800 C28 H28B 0.9800 C28 H28C 0.9800 O29 C30 1.4431(14) C30 C31 1.5079(17) C30 H30A 0.9900 C30 H30B 0.9900 C31 H31A 0.9800 C31 H31B 0.9800 C31 H31C 0.9800 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 N12 H12 O26 0.93 2.02 2.7323(13) 131.5 . N12 H12 O25 0.93 2.62 3.2181(13) 122.7 4_666 O19 H19 O21 0.84 1.81 2.5492(12) 145.7 . 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 C8 C1 C2 C3 78.54(12) C10 C1 C2 C3 -165.71(9) C9 C1 C2 C3 -40.98(13) C1 C2 C3 O19 -169.45(9) C1 C2 C3 C4 12.94(16) O19 C3 C4 C20 -1.82(17) C2 C3 C4 C20 175.51(10) O19 C3 C4 C5 176.71(10) C2 C3 C4 C5 -5.95(17) C3 C4 C5 C9 28.40(14) C20 C4 C5 C9 -153.10(10) C3 C4 C5 C6 -93.95(13) C20 C4 C5 C6 84.54(12) C4 C5 C6 C7 62.39(12) C9 C5 C6 C7 -60.14(12) C5 C6 C7 O25 -132.57(12) C5 C6 C7 C8 49.38(13) O25 C7 C8 C1 136.87(12) C6 C7 C8 C1 -45.07(14) C2 C1 C8 C7 -71.46(13) C10 C1 C8 C7 172.66(10) C9 C1 C8 C7 47.41(13) C4 C5 C9 O29 -179.48(9) C6 C5 C9 O29 -57.15(11) C4 C5 C9 O26 59.00(12) C6 C5 C9 O26 -178.67(9) C4 C5 C9 C1 -56.99(12) C6 C5 C9 C1 65.34(12) C2 C1 C9 O29 179.37(9) C8 C1 C9 O29 58.91(12) C10 C1 C9 O29 -61.12(13) C2 C1 C9 O26 -56.48(11) C8 C1 C9 O26 -176.94(9) C10 C1 C9 O26 63.03(12) C2 C1 C9 C5 63.56(11) C8 C1 C9 C5 -56.90(12) C10 C1 C9 C5 -176.93(9) C2 C1 C10 O11 -109.52(12) C8 C1 C10 O11 8.89(15) C9 C1 C10 O11 130.29(12) C2 C1 C10 N12 67.43(12) C8 C1 C10 N12 -174.16(10) C9 C1 C10 N12 -52.76(14) O11 C10 N12 C13 -10.95(19) C1 C10 N12 C13 172.20(11) C10 N12 C13 C14 -165.52(12) C10 N12 C13 C18 14.60(19) C18 C13 C14 C15 0.54(19) N12 C13 C14 C15 -179.35(12) C13 C14 C15 C16 -0.2(2) C14 C15 C16 C17 -0.5(2) C15 C16 C17 C18 1.0(2) C16 C17 C18 C13 -0.68(19) C14 C13 C18 C17 -0.10(18) N12 C13 C18 C17 179.79(11) C3 C4 C20 O21 -0.36(17) C5 C4 C20 O21 -178.89(10) C3 C4 C20 O22 179.76(10) C5 C4 C20 O22 1.22(15) O21 C20 O22 C23 -2.62(15) C4 C20 O22 C23 177.27(9) C20 O22 C23 C24 -79.94(13) O29 C9 O26 C27 -60.99(12) C5 C9 O26 C27 55.58(13) C1 C9 O26 C27 173.46(9) C9 O26 C27 C28 166.94(10) O26 C9 O29 C30 -51.01(13) C5 C9 O29 C30 -172.18(9) C1 C9 O29 C30 69.39(12) C9 O29 C30 C31 166.27(9) _journal_paper_doi 10.1021/ol050715c