# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2008 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _publ_contact_author_name 'Zhenfeng Xi' _publ_contact_author_address ; Department of Chemistry Peking University Beijing 100871 CHINA ; _publ_contact_author_email ZFXI@PKU.EDU.CN _publ_section_title ; CuCl-Mediated tandem CO insertion and annulation of 1,4-dilithio-1,3-dienes: formation of multiply substituted cyclopentadienones and/or their head-to-head dimers ; loop_ _publ_author_name 'Zhenfeng Xi' 'Qian Luo' 'Chao Wang' 'Wenxiong Zhang' data_3a _database_code_depnum_ccdc_archive 'CCDC 668730' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C34 H56 O2' _chemical_formula_weight 496.79 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M Aba2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z' 'x+1/2, -y+1/2, z' '-x+1/2, y+1/2, z' 'x, y+1/2, z+1/2' '-x, -y+1/2, z+1/2' 'x+1/2, -y+1, z+1/2' '-x+1/2, y+1, z+1/2' _cell_length_a 19.655(4) _cell_length_b 20.326(4) _cell_length_c 16.036(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 6407(2) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 11916 _cell_measurement_theta_min 1.92 _cell_measurement_theta_max 25.02 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.030 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2208 _exptl_absorpt_coefficient_mu 0.061 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.973 _exptl_absorpt_correction_T_max 0.989 _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 11916 _diffrn_reflns_av_R_equivalents 0.0506 _diffrn_reflns_av_sigmaI/netI 0.1090 _diffrn_reflns_limit_h_min -23 _diffrn_reflns_limit_h_max 23 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.92 _diffrn_reflns_theta_max 25.02 _reflns_number_total 2929 _reflns_number_gt 1209 _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^)+(0.0400P)^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 SHELXL _refine_ls_extinction_coef 0.0044(2) _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(3) _refine_ls_number_reflns 2929 _refine_ls_number_parameters 334 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.1280 _refine_ls_R_factor_gt 0.0527 _refine_ls_wR_factor_ref 0.1210 _refine_ls_wR_factor_gt 0.1108 _refine_ls_goodness_of_fit_ref 0.985 _refine_ls_restrained_S_all 0.984 _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 O1 O 0.2532(3) 0.41123(19) 0.1063(3) 0.0841(13) Uani 1 1 d . . . O2 O 0.1021(2) 0.2501(2) 0.1883(2) 0.0839(14) Uani 1 1 d . . . C1 C 0.2426(3) 0.4179(3) 0.1816(4) 0.0567(16) Uani 1 1 d . . . C2 C 0.2874(3) 0.4505(2) 0.2402(4) 0.0477(14) Uani 1 1 d . . . C3 C 0.2596(3) 0.4480(2) 0.3175(3) 0.0450(13) Uani 1 1 d . . . C4 C 0.1895(2) 0.4163(2) 0.3174(3) 0.0460(14) Uani 1 1 d . . . C5 C 0.1793(3) 0.3921(3) 0.2264(3) 0.0492(15) Uani 1 1 d . . . C6 C 0.1886(3) 0.3172(3) 0.2545(3) 0.0462(14) Uani 1 1 d . . . C7 C 0.1227(3) 0.2791(3) 0.2503(4) 0.0586(17) Uani 1 1 d . . . C8 C 0.0873(3) 0.2830(3) 0.3299(3) 0.0546(15) Uani 1 1 d . . . C9 C 0.1238(3) 0.3183(3) 0.3834(3) 0.0493(15) Uani 1 1 d . . . C10 C 0.1914(2) 0.3406(2) 0.3481(3) 0.0419(13) Uani 1 1 d . . . C11 C 0.3540(3) 0.4768(3) 0.2113(4) 0.0614(17) Uani 1 1 d . . . H11A H 0.3756 0.4443 0.1759 0.074 Uiso 1 1 calc R . . H11B H 0.3831 0.4835 0.2594 0.074 Uiso 1 1 calc R . . C12 C 0.3484(3) 0.5416(3) 0.1632(4) 0.081(2) Uani 1 1 d . . . H12A H 0.3166 0.5359 0.1175 0.097 Uiso 1 1 calc R . . H12B H 0.3303 0.5751 0.1999 0.097 Uiso 1 1 calc R . . C13 C 0.4165(4) 0.5650(4) 0.1283(5) 0.132(3) Uani 1 1 d . . . H13A H 0.4473 0.5736 0.1734 0.198 Uiso 1 1 calc R . . H13B H 0.4097 0.6046 0.0967 0.198 Uiso 1 1 calc R . . H13C H 0.4352 0.5317 0.0927 0.198 Uiso 1 1 calc R . . C14 C 0.2932(2) 0.4732(2) 0.3956(3) 0.0523(15) Uani 1 1 d . . . H14A H 0.3370 0.4517 0.4009 0.063 Uiso 1 1 calc R . . H14B H 0.2658 0.4595 0.4428 0.063 Uiso 1 1 calc R . . C15 C 0.3047(3) 0.5466(3) 0.4029(4) 0.094(2) Uani 1 1 d . . . H15A H 0.3330 0.5609 0.3567 0.112 Uiso 1 1 calc R . . H15B H 0.2612 0.5688 0.3978 0.112 Uiso 1 1 calc R . . C16 C 0.3375(4) 0.5674(3) 0.4826(4) 0.106(3) Uani 1 1 d . . . H16A H 0.3094 0.5543 0.5287 0.159 Uiso 1 1 calc R . . H16B H 0.3428 0.6143 0.4831 0.159 Uiso 1 1 calc R . . H16C H 0.3813 0.5469 0.4874 0.159 Uiso 1 1 calc R . . C17 C 0.1367(2) 0.4612(2) 0.3582(3) 0.0526(15) Uani 1 1 d . . . H17A H 0.1472 0.4646 0.4171 0.063 Uiso 1 1 calc R . . H17B H 0.0924 0.4403 0.3534 0.063 Uiso 1 1 calc R . . C18 C 0.1315(3) 0.5308(3) 0.3223(5) 0.088(2) Uani 1 1 d . . . H18A H 0.1754 0.5521 0.3273 0.105 Uiso 1 1 calc R . . H18B H 0.1206 0.5278 0.2634 0.105 Uiso 1 1 calc R . . C19 C 0.0794(4) 0.5723(3) 0.3641(6) 0.132(3) Uani 1 1 d . . . H19A H 0.0352 0.5532 0.3561 0.198 Uiso 1 1 calc R . . H19B H 0.0802 0.6157 0.3405 0.198 Uiso 1 1 calc R . . H19C H 0.0892 0.5748 0.4226 0.198 Uiso 1 1 calc R . . C20 C 0.1111(5) 0.4100(3) 0.1820(4) 0.117(3) Uani 1 1 d . . . H20A H 0.0753 0.3976 0.2208 0.140 Uiso 1 1 calc R . . H20B H 0.1102 0.4576 0.1790 0.140 Uiso 1 1 calc R . . C21 C 0.0892(4) 0.3877(5) 0.1035(8) 0.222(6) Uani 1 1 d D . . H21A H 0.1008 0.3416 0.0977 0.266 Uiso 1 1 calc R . . H21B H 0.1135 0.4118 0.0605 0.266 Uiso 1 1 calc R . . C22 C 0.0123(4) 0.3962(6) 0.0896(7) 0.196(6) Uani 1 1 d D . . H22A H -0.0097 0.3542 0.0943 0.294 Uiso 1 1 calc R . . H22B H 0.0044 0.4140 0.0350 0.294 Uiso 1 1 calc R . . H22C H -0.0057 0.4256 0.1309 0.294 Uiso 1 1 calc R . . C23 C 0.2476(3) 0.2803(3) 0.2130(3) 0.0596(16) Uani 1 1 d . . . H23A H 0.2462 0.2897 0.1537 0.071 Uiso 1 1 calc R . . H23B H 0.2898 0.2984 0.2344 0.071 Uiso 1 1 calc R . . C24 C 0.2502(5) 0.2068(3) 0.2237(5) 0.114(3) Uani 1 1 d . . . H24A H 0.2514 0.1971 0.2829 0.137 Uiso 1 1 calc R . . H24B H 0.2084 0.1883 0.2015 0.137 Uiso 1 1 calc R . . C25 C 0.3078(4) 0.1737(3) 0.1837(5) 0.114(3) Uani 1 1 d . . . H25A H 0.3496 0.1909 0.2057 0.171 Uiso 1 1 calc R . . H25B H 0.3061 0.1812 0.1246 0.171 Uiso 1 1 calc R . . H25C H 0.3053 0.1273 0.1946 0.171 Uiso 1 1 calc R . . C26 C 0.0194(3) 0.2486(3) 0.3381(4) 0.0686(18) Uani 1 1 d . . . H26A H -0.0079 0.2582 0.2893 0.082 Uiso 1 1 calc R . . H26B H -0.0043 0.2660 0.3864 0.082 Uiso 1 1 calc R . . C27 C 0.0261(3) 0.1745(3) 0.3473(4) 0.092(2) Uani 1 1 d . . . H27A H 0.0528 0.1577 0.3011 0.111 Uiso 1 1 calc R . . H27B H 0.0507 0.1649 0.3983 0.111 Uiso 1 1 calc R . . C28 C -0.0416(3) 0.1386(4) 0.3493(5) 0.134(3) Uani 1 1 d . . . H28A H -0.0672 0.1526 0.3971 0.200 Uiso 1 1 calc R . . H28B H -0.0337 0.0920 0.3526 0.200 Uiso 1 1 calc R . . H28C H -0.0667 0.1484 0.2995 0.200 Uiso 1 1 calc R . . C29 C 0.1014(3) 0.3367(3) 0.4716(4) 0.0725(19) Uani 1 1 d . . . H29A H 0.1384 0.3605 0.4980 0.087 Uiso 1 1 calc R . . H29B H 0.0633 0.3668 0.4671 0.087 Uiso 1 1 calc R . . C30 C 0.0815(5) 0.2832(4) 0.5268(4) 0.131(3) Uani 1 1 d . . . H30A H 0.1201 0.2541 0.5346 0.157 Uiso 1 1 calc R . . H30B H 0.0455 0.2580 0.5003 0.157 Uiso 1 1 calc R . . C31 C 0.0569(3) 0.3063(4) 0.6111(4) 0.116(3) Uani 1 1 d . . . H31A H 0.0935 0.3277 0.6399 0.173 Uiso 1 1 calc R . . H31B H 0.0418 0.2691 0.6430 0.173 Uiso 1 1 calc R . . H31C H 0.0200 0.3366 0.6039 0.173 Uiso 1 1 calc R . . C32 C 0.2516(3) 0.3213(2) 0.4041(3) 0.0552(15) Uani 1 1 d . . . H32A H 0.2517 0.3500 0.4525 0.066 Uiso 1 1 calc R . . H32B H 0.2934 0.3293 0.3737 0.066 Uiso 1 1 calc R . . C33 C 0.2520(4) 0.2492(3) 0.4349(5) 0.094(2) Uani 1 1 d . . . H33A H 0.2163 0.2437 0.4761 0.112 Uiso 1 1 calc R . . H33B H 0.2415 0.2205 0.3882 0.112 Uiso 1 1 calc R . . C34 C 0.3175(4) 0.2281(3) 0.4719(5) 0.094(2) Uani 1 1 d . . . H34A H 0.3527 0.2308 0.4306 0.140 Uiso 1 1 calc R . . H34B H 0.3136 0.1836 0.4912 0.140 Uiso 1 1 calc R . . H34C H 0.3286 0.2564 0.5179 0.140 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 0.127(4) 0.076(3) 0.050(3) -0.001(2) 0.008(3) -0.022(3) O2 0.098(3) 0.091(3) 0.063(3) -0.018(3) -0.007(3) -0.039(3) C1 0.078(5) 0.046(4) 0.046(4) 0.004(3) 0.004(4) -0.004(4) C2 0.052(4) 0.035(3) 0.057(4) 0.004(3) 0.005(3) 0.000(3) C3 0.050(3) 0.034(3) 0.051(3) -0.003(3) 0.001(3) -0.002(3) C4 0.050(3) 0.040(3) 0.048(3) -0.003(3) 0.003(3) -0.002(3) C5 0.060(4) 0.050(4) 0.037(3) 0.000(3) -0.014(3) -0.002(3) C6 0.050(4) 0.047(3) 0.042(3) -0.003(3) 0.003(3) -0.009(3) C7 0.070(5) 0.047(4) 0.059(4) -0.007(3) 0.000(4) -0.007(3) C8 0.056(3) 0.048(4) 0.060(4) 0.003(3) 0.005(4) -0.007(3) C9 0.049(4) 0.054(4) 0.045(3) -0.004(3) 0.000(3) -0.011(3) C10 0.050(3) 0.037(3) 0.039(3) -0.002(3) -0.002(3) -0.004(3) C11 0.059(4) 0.052(4) 0.073(4) 0.007(3) 0.011(3) 0.000(3) C12 0.073(5) 0.062(5) 0.107(5) 0.023(4) 0.016(4) -0.012(4) C13 0.125(7) 0.133(8) 0.138(8) 0.029(6) 0.030(6) -0.032(6) C14 0.054(4) 0.050(4) 0.052(4) -0.004(3) 0.002(3) -0.007(3) C15 0.138(6) 0.047(4) 0.096(5) 0.004(4) -0.031(5) -0.025(4) C16 0.153(7) 0.081(5) 0.084(5) -0.016(4) -0.025(5) -0.050(5) C17 0.046(3) 0.050(4) 0.062(4) -0.007(3) 0.008(3) 0.001(3) C18 0.086(5) 0.049(4) 0.128(6) 0.006(4) 0.008(5) 0.013(4) C19 0.102(5) 0.084(5) 0.210(9) 0.000(6) 0.048(6) 0.036(5) C20 0.220(9) 0.052(5) 0.079(6) -0.003(4) -0.080(6) 0.003(5) C21 0.41(2) 0.104(9) 0.147(11) 0.031(8) -0.023(13) -0.004(11) C22 0.104(7) 0.251(13) 0.234(12) -0.023(10) -0.129(8) 0.024(8) C23 0.081(4) 0.049(4) 0.049(3) -0.006(3) 0.005(3) 0.000(4) C24 0.166(7) 0.057(5) 0.120(6) 0.008(5) 0.065(6) 0.022(6) C25 0.163(7) 0.071(5) 0.108(6) 0.001(5) 0.028(6) 0.043(5) C26 0.056(4) 0.080(5) 0.070(5) 0.000(4) 0.003(3) -0.011(4) C27 0.087(5) 0.087(5) 0.104(6) -0.015(5) 0.014(4) -0.028(4) C28 0.119(6) 0.133(7) 0.149(8) -0.003(6) 0.004(6) -0.097(5) C29 0.081(5) 0.069(5) 0.067(4) 0.000(4) 0.006(4) -0.023(4) C30 0.209(10) 0.123(7) 0.063(5) -0.008(5) 0.006(6) -0.048(7) C31 0.123(6) 0.157(8) 0.067(5) -0.014(5) 0.039(5) -0.030(6) C32 0.065(4) 0.048(3) 0.053(3) -0.001(3) 0.011(3) 0.002(3) C33 0.125(6) 0.056(4) 0.100(5) 0.016(4) -0.035(5) -0.002(5) C34 0.109(6) 0.064(4) 0.107(5) 0.018(4) -0.032(5) 0.019(4) _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 C1 1.233(6) . ? O2 C7 1.226(6) . ? C1 C2 1.449(7) . ? C1 C5 1.529(7) . ? C2 C3 1.354(7) . ? C2 C11 1.488(7) . ? C3 C14 1.506(7) . ? C3 C4 1.522(7) . ? C4 C17 1.529(6) . ? C4 C5 1.552(7) . ? C4 C10 1.616(7) . ? C5 C20 1.561(8) . ? C5 C6 1.598(7) . ? C6 C7 1.510(7) . ? C6 C23 1.533(7) . ? C6 C10 1.575(7) . ? C7 C8 1.456(7) . ? C8 C9 1.328(6) . ? C8 C26 1.512(7) . ? C9 C10 1.514(6) . ? C9 C29 1.528(7) . ? C10 C32 1.536(7) . ? C11 C12 1.530(7) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 C13 1.527(8) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C13 H13A 0.9600 . ? C13 H13B 0.9600 . ? C13 H13C 0.9600 . ? C14 C15 1.513(7) . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C15 C16 1.493(8) . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C16 H16A 0.9600 . ? C16 H16B 0.9600 . ? C16 H16C 0.9600 . ? C17 C18 1.530(7) . ? C17 H17A 0.9700 . ? C17 H17B 0.9700 . ? C18 C19 1.486(8) . ? C18 H18A 0.9700 . ? C18 H18B 0.9700 . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 0.9600 . ? C20 C21 1.406(13) . ? C20 H20A 0.9700 . ? C20 H20B 0.9700 . ? C21 C22 1.538(2) . ? C21 H21A 0.9700 . ? C21 H21B 0.9700 . ? C22 H22A 0.9600 . ? C22 H22B 0.9600 . ? C22 H22C 0.9600 . ? C23 C24 1.505(7) . ? C23 H23A 0.9700 . ? C23 H23B 0.9700 . ? C24 C25 1.465(8) . ? C24 H24A 0.9700 . ? C24 H24B 0.9700 . ? C25 H25A 0.9600 . ? C25 H25B 0.9600 . ? C25 H25C 0.9600 . ? C26 C27 1.520(8) . ? C26 H26A 0.9700 . ? C26 H26B 0.9700 . ? C27 C28 1.517(7) . ? C27 H27A 0.9700 . ? C27 H27B 0.9700 . ? C28 H28A 0.9600 . ? C28 H28B 0.9600 . ? C28 H28C 0.9600 . ? C29 C30 1.456(8) . ? C29 H29A 0.9700 . ? C29 H29B 0.9700 . ? C30 C31 1.509(9) . ? C30 H30A 0.9700 . ? C30 H30B 0.9700 . ? C31 H31A 0.9600 . ? C31 H31B 0.9600 . ? C31 H31C 0.9600 . ? C32 C33 1.546(7) . ? C32 H32A 0.9700 . ? C32 H32B 0.9700 . ? C33 C34 1.481(9) . ? C33 H33A 0.9700 . ? C33 H33B 0.9700 . ? C34 H34A 0.9600 . ? C34 H34B 0.9600 . ? C34 H34C 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 125.7(6) . . ? O1 C1 C5 124.1(5) . . ? C2 C1 C5 110.3(5) . . ? C3 C2 C1 109.4(5) . . ? C3 C2 C11 130.7(5) . . ? C1 C2 C11 119.8(5) . . ? C2 C3 C14 124.9(5) . . ? C2 C3 C4 112.3(5) . . ? C14 C3 C4 122.8(5) . . ? C3 C4 C17 111.2(4) . . ? C3 C4 C5 104.6(4) . . ? C17 C4 C5 120.2(4) . . ? C3 C4 C10 112.4(4) . . ? C17 C4 C10 117.0(4) . . ? C5 C4 C10 89.3(4) . . ? C1 C5 C4 103.2(4) . . ? C1 C5 C20 113.9(5) . . ? C4 C5 C20 117.8(5) . . ? C1 C5 C6 111.4(4) . . ? C4 C5 C6 91.2(4) . . ? C20 C5 C6 116.6(4) . . ? C7 C6 C23 112.2(5) . . ? C7 C6 C10 103.1(4) . . ? C23 C6 C10 122.2(4) . . ? C7 C6 C5 112.2(4) . . ? C23 C6 C5 115.5(4) . . ? C10 C6 C5 89.2(4) . . ? O2 C7 C8 125.4(6) . . ? O2 C7 C6 124.5(5) . . ? C8 C7 C6 110.0(5) . . ? C9 C8 C7 109.7(5) . . ? C9 C8 C26 132.1(5) . . ? C7 C8 C26 118.2(5) . . ? C8 C9 C10 113.2(5) . . ? C8 C9 C29 125.0(5) . . ? C10 C9 C29 121.8(5) . . ? C9 C10 C32 112.3(4) . . ? C9 C10 C6 103.6(4) . . ? C32 C10 C6 120.6(4) . . ? C9 C10 C4 112.2(4) . . ? C32 C10 C4 116.1(4) . . ? C6 C10 C4 89.8(3) . . ? C2 C11 C12 113.8(5) . . ? C2 C11 H11A 108.8 . . ? C12 C11 H11A 108.8 . . ? C2 C11 H11B 108.8 . . ? C12 C11 H11B 108.8 . . ? H11A C11 H11B 107.7 . . ? C13 C12 C11 113.0(5) . . ? C13 C12 H12A 109.0 . . ? C11 C12 H12A 109.0 . . ? C13 C12 H12B 109.0 . . ? C11 C12 H12B 109.0 . . ? H12A C12 H12B 107.8 . . ? C12 C13 H13A 109.5 . . ? C12 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C12 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C3 C14 C15 117.7(5) . . ? C3 C14 H14A 107.9 . . ? C15 C14 H14A 107.9 . . ? C3 C14 H14B 107.9 . . ? C15 C14 H14B 107.9 . . ? H14A C14 H14B 107.2 . . ? C16 C15 C14 114.1(5) . . ? C16 C15 H15A 108.7 . . ? C14 C15 H15A 108.7 . . ? C16 C15 H15B 108.7 . . ? C14 C15 H15B 108.7 . . ? H15A C15 H15B 107.6 . . ? C15 C16 H16A 109.5 . . ? C15 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C15 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C4 C17 C18 115.9(5) . . ? C4 C17 H17A 108.3 . . ? C18 C17 H17A 108.3 . . ? C4 C17 H17B 108.3 . . ? C18 C17 H17B 108.3 . . ? H17A C17 H17B 107.4 . . ? C19 C18 C17 113.7(6) . . ? C19 C18 H18A 108.8 . . ? C17 C18 H18A 108.8 . . ? C19 C18 H18B 108.8 . . ? C17 C18 H18B 108.8 . . ? H18A C18 H18B 107.7 . . ? C18 C19 H19A 109.5 . . ? C18 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C18 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C21 C20 C5 126.6(7) . . ? C21 C20 H20A 105.7 . . ? C5 C20 H20A 105.7 . . ? C21 C20 H20B 105.7 . . ? C5 C20 H20B 105.7 . . ? H20A C20 H20B 106.1 . . ? C20 C21 C22 113.2(10) . . ? C20 C21 H21A 108.9 . . ? C22 C21 H21A 108.9 . . ? C20 C21 H21B 108.9 . . ? C22 C21 H21B 108.9 . . ? H21A C21 H21B 107.8 . . ? C21 C22 H22A 109.5 . . ? C21 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C21 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C24 C23 C6 117.5(6) . . ? C24 C23 H23A 107.9 . . ? C6 C23 H23A 107.9 . . ? C24 C23 H23B 107.9 . . ? C6 C23 H23B 107.9 . . ? H23A C23 H23B 107.2 . . ? C25 C24 C23 115.7(6) . . ? C25 C24 H24A 108.4 . . ? C23 C24 H24A 108.4 . . ? C25 C24 H24B 108.4 . . ? C23 C24 H24B 108.4 . . ? H24A C24 H24B 107.4 . . ? C24 C25 H25A 109.5 . . ? C24 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? C24 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? C8 C26 C27 113.0(5) . . ? C8 C26 H26A 109.0 . . ? C27 C26 H26A 109.0 . . ? C8 C26 H26B 109.0 . . ? C27 C26 H26B 109.0 . . ? H26A C26 H26B 107.8 . . ? C28 C27 C26 113.8(6) . . ? C28 C27 H27A 108.8 . . ? C26 C27 H27A 108.8 . . ? C28 C27 H27B 108.8 . . ? C26 C27 H27B 108.8 . . ? H27A C27 H27B 107.7 . . ? 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 . . ? C30 C29 C9 117.2(6) . . ? C30 C29 H29A 108.0 . . ? C9 C29 H29A 108.0 . . ? C30 C29 H29B 108.0 . . ? C9 C29 H29B 108.0 . . ? H29A C29 H29B 107.2 . . ? C29 C30 C31 113.5(7) . . ? C29 C30 H30A 108.9 . . ? C31 C30 H30A 108.9 . . ? C29 C30 H30B 108.9 . . ? C31 C30 H30B 108.9 . . ? H30A C30 H30B 107.7 . . ? 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 . . ? C10 C32 C33 115.6(5) . . ? C10 C32 H32A 108.4 . . ? C33 C32 H32A 108.4 . . ? C10 C32 H32B 108.4 . . ? C33 C32 H32B 108.4 . . ? H32A C32 H32B 107.4 . . ? C34 C33 C32 113.9(6) . . ? C34 C33 H33A 108.8 . . ? C32 C33 H33A 108.8 . . ? C34 C33 H33B 108.8 . . ? C32 C33 H33B 108.8 . . ? H33A C33 H33B 107.7 . . ? C33 C34 H34A 109.5 . . ? C33 C34 H34B 109.5 . . ? H34A C34 H34B 109.5 . . ? C33 C34 H34C 109.5 . . ? H34A C34 H34C 109.5 . . ? H34B C34 H34C 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 O1 C1 C2 C3 -179.6(5) . . . . ? C5 C1 C2 C3 0.3(6) . . . . ? O1 C1 C2 C11 -2.7(9) . . . . ? C5 C1 C2 C11 177.2(4) . . . . ? C1 C2 C3 C14 176.3(5) . . . . ? C11 C2 C3 C14 -0.1(9) . . . . ? C1 C2 C3 C4 -3.6(6) . . . . ? C11 C2 C3 C4 180.0(5) . . . . ? C2 C3 C4 C17 -125.8(5) . . . . ? C14 C3 C4 C17 54.2(6) . . . . ? C2 C3 C4 C5 5.3(6) . . . . ? C14 C3 C4 C5 -174.6(5) . . . . ? C2 C3 C4 C10 100.8(5) . . . . ? C14 C3 C4 C10 -79.2(6) . . . . ? O1 C1 C5 C4 -177.2(5) . . . . ? C2 C1 C5 C4 2.9(6) . . . . ? O1 C1 C5 C20 -48.4(8) . . . . ? C2 C1 C5 C20 131.8(5) . . . . ? O1 C1 C5 C6 86.1(7) . . . . ? C2 C1 C5 C6 -93.7(5) . . . . ? C3 C4 C5 C1 -4.6(5) . . . . ? C17 C4 C5 C1 121.1(5) . . . . ? C10 C4 C5 C1 -117.7(4) . . . . ? C3 C4 C5 C20 -131.1(5) . . . . ? C17 C4 C5 C20 -5.4(7) . . . . ? C10 C4 C5 C20 115.8(5) . . . . ? C3 C4 C5 C6 107.7(4) . . . . ? C17 C4 C5 C6 -126.6(4) . . . . ? C10 C4 C5 C6 -5.3(4) . . . . ? C1 C5 C6 C7 -146.0(5) . . . . ? C4 C5 C6 C7 109.3(5) . . . . ? C20 C5 C6 C7 -12.8(7) . . . . ? C1 C5 C6 C23 -15.6(6) . . . . ? C4 C5 C6 C23 -120.3(5) . . . . ? C20 C5 C6 C23 117.6(6) . . . . ? C1 C5 C6 C10 110.1(4) . . . . ? C4 C5 C6 C10 5.4(4) . . . . ? C20 C5 C6 C10 -116.7(5) . . . . ? C23 C6 C7 O2 -43.7(8) . . . . ? C10 C6 C7 O2 -177.1(5) . . . . ? C5 C6 C7 O2 88.3(7) . . . . ? C23 C6 C7 C8 137.3(5) . . . . ? C10 C6 C7 C8 3.9(6) . . . . ? C5 C6 C7 C8 -90.7(5) . . . . ? O2 C7 C8 C9 -179.9(6) . . . . ? C6 C7 C8 C9 -0.9(6) . . . . ? O2 C7 C8 C26 0.2(9) . . . . ? C6 C7 C8 C26 179.2(5) . . . . ? C7 C8 C9 C10 -2.8(6) . . . . ? C26 C8 C9 C10 177.1(5) . . . . ? C7 C8 C9 C29 176.1(5) . . . . ? C26 C8 C9 C29 -3.9(10) . . . . ? C8 C9 C10 C32 -126.6(5) . . . . ? C29 C9 C10 C32 54.5(6) . . . . ? C8 C9 C10 C6 5.1(6) . . . . ? C29 C9 C10 C6 -173.9(5) . . . . ? C8 C9 C10 C4 100.5(5) . . . . ? C29 C9 C10 C4 -78.5(6) . . . . ? C7 C6 C10 C9 -5.1(5) . . . . ? C23 C6 C10 C9 -132.4(5) . . . . ? C5 C6 C10 C9 107.6(4) . . . . ? C7 C6 C10 C32 121.6(5) . . . . ? C23 C6 C10 C32 -5.8(7) . . . . ? C5 C6 C10 C32 -125.8(4) . . . . ? C7 C6 C10 C4 -117.9(4) . . . . ? C23 C6 C10 C4 114.8(5) . . . . ? C5 C6 C10 C4 -5.2(4) . . . . ? C3 C4 C10 C9 155.2(5) . . . . ? C17 C4 C10 C9 24.7(6) . . . . ? C5 C4 C10 C9 -99.2(4) . . . . ? C3 C4 C10 C32 24.2(6) . . . . ? C17 C4 C10 C32 -106.3(5) . . . . ? C5 C4 C10 C32 129.7(4) . . . . ? C3 C4 C10 C6 -100.1(4) . . . . ? C17 C4 C10 C6 129.3(4) . . . . ? C5 C4 C10 C6 5.4(4) . . . . ? C3 C2 C11 C12 -106.9(7) . . . . ? C1 C2 C11 C12 77.0(6) . . . . ? C2 C11 C12 C13 -175.5(6) . . . . ? C2 C3 C14 C15 66.2(7) . . . . ? C4 C3 C14 C15 -113.8(6) . . . . ? C3 C14 C15 C16 179.4(6) . . . . ? C3 C4 C17 C18 54.4(6) . . . . ? C5 C4 C17 C18 -68.2(7) . . . . ? C10 C4 C17 C18 -174.5(5) . . . . ? C4 C17 C18 C19 180.0(6) . . . . ? C1 C5 C20 C21 65.5(10) . . . . ? C4 C5 C20 C21 -173.4(8) . . . . ? C6 C5 C20 C21 -66.6(10) . . . . ? C5 C20 C21 C22 162.0(8) . . . . ? C7 C6 C23 C24 -37.6(8) . . . . ? C10 C6 C23 C24 85.6(8) . . . . ? C5 C6 C23 C24 -168.0(6) . . . . ? C6 C23 C24 C25 -179.4(6) . . . . ? C9 C8 C26 C27 -103.9(8) . . . . ? C7 C8 C26 C27 76.0(7) . . . . ? C8 C26 C27 C28 -175.8(6) . . . . ? C8 C9 C29 C30 55.0(9) . . . . ? C10 C9 C29 C30 -126.2(7) . . . . ? C9 C29 C30 C31 -177.2(6) . . . . ? C9 C10 C32 C33 47.6(6) . . . . ? C6 C10 C32 C33 -75.0(6) . . . . ? C4 C10 C32 C33 178.6(5) . . . . ? C10 C32 C33 C34 166.7(6) . . . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 25.02 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.398 _refine_diff_density_min -0.167 _refine_diff_density_rms 0.034 data_a _database_code_depnum_ccdc_archive 'CCDC 668731' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C34 H52 O2' _chemical_formula_weight 492.76 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 C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 22.715(5) _cell_length_b 8.6051(17) _cell_length_c 16.731(3) _cell_angle_alpha 90.00 _cell_angle_beta 109.25(3) _cell_angle_gamma 90.00 _cell_volume 3087.4(11) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.060 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1088 _exptl_absorpt_coefficient_mu 0.063 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_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 ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 2700 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0927 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 26 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.55 _diffrn_reflns_theta_max 25.03 _reflns_number_total 2700 _reflns_number_gt 923 _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^)+(0.0600P)^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 SHELXL _refine_ls_extinction_coef 0.0024(6) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2700 _refine_ls_number_parameters 174 _refine_ls_number_restraints 7 _refine_ls_R_factor_all 0.1758 _refine_ls_R_factor_gt 0.0685 _refine_ls_wR_factor_ref 0.1757 _refine_ls_wR_factor_gt 0.1558 _refine_ls_goodness_of_fit_ref 1.037 _refine_ls_restrained_S_all 1.037 _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 O1 O 0.44054(13) 0.5791(3) 0.33617(17) 0.0939(10) Uani 1 1 d . . . C1 C 0.45601(18) 0.7134(5) 0.3292(2) 0.0662(11) Uani 1 1 d . . . C2 C 0.42575(16) 0.8532(5) 0.3469(2) 0.0668(10) Uani 1 1 d . . . C3 C 0.45506(16) 0.9793(4) 0.3325(2) 0.0623(10) Uani 1 1 d . . . C4 C 0.44449(19) 1.1440(5) 0.3515(2) 0.0816(12) Uani 1 1 d . . . H4A H 0.4137 1.1483 0.3802 0.098 Uiso 1 1 calc R . . H4B H 0.4284 1.2019 0.2990 0.098 Uiso 1 1 calc R . . C5 C 0.5063(2) 1.2193(4) 0.4083(2) 0.0852(13) Uani 1 1 d . . . H5A H 0.4998 1.3292 0.4153 0.102 Uiso 1 1 calc R . . H5B H 0.5193 1.1711 0.4638 0.102 Uiso 1 1 calc R . . C6 C 0.5566(2) 1.1983(4) 0.3683(3) 0.0858(13) Uani 1 1 d . . . H6A H 0.5950 1.2441 0.4049 0.103 Uiso 1 1 calc R . . H6B H 0.5445 1.2535 0.3147 0.103 Uiso 1 1 calc R . . C7 C 0.56832(16) 1.0295(4) 0.3528(2) 0.0634(10) Uani 1 1 d . . . H7A H 0.5863 0.9781 0.4071 0.076 Uiso 1 1 calc R . . H7B H 0.5987 1.0247 0.3236 0.076 Uiso 1 1 calc R . . C8 C 0.51049(15) 0.9413(4) 0.30139(18) 0.0532(9) Uani 1 1 d . . . C9 C 0.51008(16) 0.7598(4) 0.30043(19) 0.0571(10) Uani 1 1 d . . . C10 C 0.37028(16) 0.8453(5) 0.3764(2) 0.0940(13) Uani 1 1 d D . . H10A H 0.3732 0.7509 0.4091 0.113 Uiso 1 1 calc R . . H10B H 0.3723 0.9323 0.4140 0.113 Uiso 1 1 calc R . . C11 C 0.30801(17) 0.8478(7) 0.3080(3) 0.1321(19) Uani 1 1 d D . . H11A H 0.3034 0.9420 0.2746 0.159 Uiso 1 1 calc R . . H11B H 0.3038 0.7591 0.2707 0.159 Uiso 1 1 calc R . . C12 C 0.2603(3) 0.8418(9) 0.3501(5) 0.210(3) Uani 1 1 d D . . H12A H 0.2674 0.9270 0.3902 0.251 Uiso 1 1 calc R . . H12B H 0.2652 0.7456 0.3819 0.251 Uiso 1 1 calc R . . C13 C 0.1953(4) 0.8514(9) 0.2912(5) 0.234(4) Uani 1 1 d D . . H13A H 0.1669 0.8475 0.3228 0.350 Uiso 1 1 calc R . . H13B H 0.1872 0.7656 0.2524 0.350 Uiso 1 1 calc R . . H13C H 0.1897 0.9472 0.2602 0.350 Uiso 1 1 calc R . . C14 C 0.56947(16) 0.6717(4) 0.34794(18) 0.0717(11) Uani 1 1 d D . . H14A H 0.6040 0.7203 0.3354 0.086 Uiso 1 1 calc R . . H14B H 0.5656 0.5665 0.3260 0.086 Uiso 1 1 calc R . . C15 C 0.58617(17) 0.6630(4) 0.44555(18) 0.0933(13) Uani 1 1 d D . . H15A H 0.5549 0.6022 0.4594 0.112 Uiso 1 1 calc R . . H15B H 0.5862 0.7668 0.4681 0.112 Uiso 1 1 calc R . . C16 C 0.6514(2) 0.5875(8) 0.4868(3) 0.155(2) Uani 1 1 d D . . C17A C 0.6809(3) 0.6169(10) 0.5833(3) 0.163(4) Uani 0.796(12) 1 d PD . . C17B C 0.6997(7) 0.7172(16) 0.5073(14) 0.102(12) Uani 0.204(12) 1 d PD . . 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 0.104(2) 0.0693(19) 0.117(2) 0.0203(17) 0.0494(17) -0.0099(18) C1 0.070(3) 0.066(3) 0.065(3) 0.010(2) 0.024(2) -0.003(3) C2 0.068(3) 0.076(3) 0.068(2) 0.010(2) 0.037(2) 0.008(3) C3 0.066(3) 0.062(3) 0.064(2) 0.004(2) 0.028(2) 0.015(2) C4 0.102(3) 0.079(3) 0.080(3) 0.005(3) 0.053(2) 0.023(3) C5 0.120(4) 0.064(3) 0.076(3) -0.012(2) 0.038(3) 0.003(3) C6 0.122(4) 0.062(3) 0.079(3) -0.010(2) 0.040(3) -0.014(2) C7 0.068(3) 0.056(2) 0.067(2) -0.005(2) 0.024(2) -0.004(2) C8 0.052(2) 0.050(2) 0.064(2) -0.0012(17) 0.0258(19) -0.0002(19) C9 0.064(3) 0.047(2) 0.064(2) 0.0049(17) 0.026(2) 0.009(2) C10 0.079(3) 0.122(3) 0.102(3) 0.024(3) 0.058(3) 0.011(3) C11 0.057(3) 0.191(5) 0.170(4) 0.007(4) 0.066(3) 0.002(4) C12 0.174(7) 0.231(8) 0.238(9) -0.028(7) 0.087(7) -0.011(7) C13 0.190(8) 0.251(9) 0.264(9) 0.016(7) 0.079(7) -0.007(8) C14 0.066(3) 0.064(3) 0.080(3) -0.001(2) 0.018(2) 0.018(2) C15 0.120(4) 0.074(3) 0.074(3) 0.002(2) 0.017(2) 0.011(3) C16 0.136(5) 0.171(6) 0.102(4) -0.002(4) -0.036(3) 0.074(5) C17A 0.126(6) 0.204(8) 0.137(7) -0.008(6) 0.013(5) 0.027(6) C17B 0.089(18) 0.105(19) 0.09(2) 0.002(14) 0.004(14) 0.012(14) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C1 1.225(4) . ? C1 C2 1.464(5) . ? C1 C9 1.513(4) . ? C2 C3 1.336(4) . ? C2 C10 1.498(4) . ? C3 C4 1.490(4) . ? C3 C8 1.548(4) . ? C4 C5 1.554(5) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C5 C6 1.513(5) . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C6 C7 1.515(4) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 C8 1.515(4) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 C9 1.562(4) . ? C8 C8 1.626(6) 2_655 ? C9 C14 1.523(4) . ? C9 C9 1.596(6) 2_655 ? C10 C11 1.498(2) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 C12 1.477(2) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 C13 1.482(2) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C13 H13A 0.9600 . ? C13 H13B 0.9600 . ? C13 H13C 0.9600 . ? C14 C15 1.5517(19) . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C15 C16 1.555(2) . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C16 C17B 1.523(2) . ? C16 C17A 1.552(2) . ? C17A C17B 1.705(18) . ? 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 126.0(4) . . ? O1 C1 C9 124.6(4) . . ? C2 C1 C9 109.4(3) . . ? C3 C2 C1 109.6(3) . . ? C3 C2 C10 128.3(4) . . ? C1 C2 C10 122.1(4) . . ? C2 C3 C4 127.5(3) . . ? C2 C3 C8 113.5(3) . . ? C4 C3 C8 118.6(3) . . ? C3 C4 C5 110.5(3) . . ? C3 C4 H4A 109.6 . . ? C5 C4 H4A 109.6 . . ? C3 C4 H4B 109.5 . . ? C5 C4 H4B 109.6 . . ? H4A C4 H4B 108.1 . . ? C6 C5 C4 109.9(3) . . ? C6 C5 H5A 109.7 . . ? C4 C5 H5A 109.7 . . ? C6 C5 H5B 109.7 . . ? C4 C5 H5B 109.7 . . ? H5A C5 H5B 108.2 . . ? C5 C6 C7 113.0(3) . . ? C5 C6 H6A 109.0 . . ? C7 C6 H6A 109.0 . . ? C5 C6 H6B 109.0 . . ? C7 C6 H6B 109.0 . . ? H6A C6 H6B 107.8 . . ? C6 C7 C8 114.1(3) . . ? C6 C7 H7A 108.7 . . ? C8 C7 H7A 108.7 . . ? C6 C7 H7B 108.7 . . ? C8 C7 H7B 108.7 . . ? H7A C7 H7B 107.6 . . ? C7 C8 C3 110.6(3) . . ? C7 C8 C9 120.5(3) . . ? C3 C8 C9 102.2(3) . . ? C7 C8 C8 119.8(3) . 2_655 ? C3 C8 C8 111.6(3) . 2_655 ? C9 C8 C8 89.45(16) . 2_655 ? C1 C9 C14 112.0(3) . . ? C1 C9 C8 105.3(3) . . ? C14 C9 C8 119.4(3) . . ? C1 C9 C9 110.9(3) . 2_655 ? C14 C9 C9 116.6(3) . 2_655 ? C8 C9 C9 90.55(16) . 2_655 ? C11 C10 C2 115.6(3) . . ? C11 C10 H10A 108.4 . . ? C2 C10 H10A 108.4 . . ? C11 C10 H10B 108.4 . . ? C2 C10 H10B 108.4 . . ? H10A C10 H10B 107.4 . . ? C12 C11 C10 107.0(4) . . ? C12 C11 H11A 110.3 . . ? C10 C11 H11A 110.3 . . ? C12 C11 H11B 110.3 . . ? C10 C11 H11B 110.3 . . ? H11A C11 H11B 108.6 . . ? C11 C12 C13 114.0(5) . . ? C11 C12 H12A 108.7 . . ? C13 C12 H12A 108.7 . . ? C11 C12 H12B 108.7 . . ? C13 C12 H12B 108.7 . . ? H12A C12 H12B 107.6 . . ? C12 C13 H13A 109.5 . . ? C12 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C12 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C9 C14 C15 116.1(3) . . ? C9 C14 H14A 108.3 . . ? C15 C14 H14A 108.3 . . ? C9 C14 H14B 108.3 . . ? C15 C14 H14B 108.3 . . ? H14A C14 H14B 107.4 . . ? C14 C15 C16 110.7(3) . . ? C14 C15 H15A 109.5 . . ? C16 C15 H15A 109.5 . . ? C14 C15 H15B 109.5 . . ? C16 C15 H15B 109.5 . . ? H15A C15 H15B 108.1 . . ? C17B C16 C17A 67.3(8) . . ? C17B C16 C15 107.7(9) . . ? C17A C16 C15 114.5(4) . . ? C16 C17A C17B 55.5(4) . . ? C16 C17B C17A 57.1(4) . . ? 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 O1 C1 C2 C3 179.9(4) . . . . ? C9 C1 C2 C3 -0.1(4) . . . . ? O1 C1 C2 C10 -0.3(6) . . . . ? C9 C1 C2 C10 179.8(3) . . . . ? C1 C2 C3 C4 -172.5(3) . . . . ? C10 C2 C3 C4 7.6(6) . . . . ? C1 C2 C3 C8 0.5(4) . . . . ? C10 C2 C3 C8 -179.3(3) . . . . ? C2 C3 C4 C5 124.3(4) . . . . ? C8 C3 C4 C5 -48.5(4) . . . . ? C3 C4 C5 C6 53.4(4) . . . . ? C4 C5 C6 C7 -57.7(4) . . . . ? C5 C6 C7 C8 54.5(4) . . . . ? C6 C7 C8 C3 -44.2(4) . . . . ? C6 C7 C8 C9 -163.2(3) . . . . ? C6 C7 C8 C8 87.9(3) . . . 2_655 ? C2 C3 C8 C7 -130.2(3) . . . . ? C4 C3 C8 C7 43.5(4) . . . . ? C2 C3 C8 C9 -0.7(4) . . . . ? C4 C3 C8 C9 173.0(3) . . . . ? C2 C3 C8 C8 93.7(3) . . . 2_655 ? C4 C3 C8 C8 -92.6(3) . . . 2_655 ? O1 C1 C9 C14 -49.0(5) . . . . ? C2 C1 C9 C14 130.9(3) . . . . ? O1 C1 C9 C8 179.7(4) . . . . ? C2 C1 C9 C8 -0.3(4) . . . . ? O1 C1 C9 C9 83.1(4) . . . 2_655 ? C2 C1 C9 C9 -96.9(3) . . . 2_655 ? C7 C8 C9 C1 123.7(3) . . . . ? C3 C8 C9 C1 0.6(3) . . . . ? C8 C8 C9 C1 -111.5(3) 2_655 . . . ? C7 C8 C9 C14 -3.2(4) . . . . ? C3 C8 C9 C14 -126.3(3) . . . . ? C8 C8 C9 C14 121.6(3) 2_655 . . . ? C7 C8 C9 C9 -124.5(3) . . . 2_655 ? C3 C8 C9 C9 112.4(3) . . . 2_655 ? C8 C8 C9 C9 0.4(4) 2_655 . . 2_655 ? C3 C2 C10 C11 88.7(5) . . . . ? C1 C2 C10 C11 -91.1(5) . . . . ? C2 C10 C11 C12 -179.1(5) . . . . ? C10 C11 C12 C13 177.1(6) . . . . ? C1 C9 C14 C15 -46.8(4) . . . . ? C8 C9 C14 C15 76.9(4) . . . . ? C9 C9 C14 C15 -176.0(3) 2_655 . . . ? C9 C14 C15 C16 -173.3(4) . . . . ? C14 C15 C16 C17B 90.2(10) . . . . ? C14 C15 C16 C17A 162.7(6) . . . . ? C15 C16 C17A C17B -99.9(10) . . . . ? C15 C16 C17B C17A 109.7(5) . . . . ? _diffrn_measured_fraction_theta_max 0.987 _diffrn_reflns_theta_full 25.03 _diffrn_measured_fraction_theta_full 0.987 _refine_diff_density_max 0.296 _refine_diff_density_min -0.168 _refine_diff_density_rms 0.048