# Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2005 data_global _journal_coden_Cambridge 182 loop_ _publ_author_name 'G. Mehta' 'Kotapalli Pallavi' 'Jayant D. Umarye' _publ_contact_author_name 'G. Mehta' _publ_contact_author_address ; Department of Organic Chemistry Indian Institute of Science Bangalore 560 012 INDIA ; _publ_contact_author_email GM@ORGCHEM.IISC.ERNET.IN _publ_requested_journal 'Chemical Communications' _publ_section_title ; A total synthesis of Guanacastepene C ; _publ_section_references ; Allen, F.H. & Kennard, O. (1993). Chem. Des. Autom. News., 8, 31-37. Altomare, A., Burla, M.C., Camalli, M., Cascarano, G.L., Giacovazzo, C. Guagliardi, A., Moliterni, A.G.G., Polidori, G. & Spagna, R. (1999) J. Appl. Cryst. 32, 115-119. Beurskens, P.T., Admiraal, G., Beurskens, G., Bosman, W.P., Garc\'ia-Granda, S., Gould, R.O., Smits, J.M.M. & Smykalla, C. (1999) The DIRDIF99 program system, Technical Report of the Crystallography Laboratory, University of Nijmegen, The Netherlands. Boer, J.L. de & Duisenberg, A.J.M. (1984). Acta Cryst. A40, C-410. Boeyens, J.C.A. (1978). J.Cryst.Mol.Struct. 8, 317-320. Cremer, D. & Pople, J.A. (1975). J. Am. Chem. Soc. 97, 1354-1358. Enraf-Nonius (1989). CAD-4 Software. Version 5. Enraf-Nonius, Delft, The Netherlands. Flack, H.D. (1983). Acta Cryst. A39, 876-881. LePage, Y. (1987). J. Appl. Cryst. 20, 264-269. Mackay, A.L. (1984). Acta Cryst. A40, 165-166. Meulenaer, J. de & Tompa, H. (1965). Acta Cryst. 19, 1014-1018. Nonius (1998). Collect Software, Nonius, Delft, The Netherlands. North, A.C.T., Phillips, D.C. & Mathews, F.S. (1968). Acta Cryst. A24, 351-359. Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, 276, 307-326. Sheldrick, G.M. SHELXL93. Program for crystal structure refinement. University of Gottingen, Germany, 1993. Sheldrick, G.M. SHELXL97. Program for crystal structure refinement. University of Gottingen, Germany, 1997. Sheldrick, G.M. SHELXS86. Program for Crystal Structure solution. University of Gottingen, Germany, 1986. Sheldrick, G.M. SHELXS97. Program for Crystal Structure solution. University of Gottingen, Germany, 1997. Spek, A.L. (1987). Acta Cryst. C43, 1233-1235. Spek, A.L. (1988). J. Appl. Cryst. 21, 578-579. Spek, A.L. (1990). Acta Cryst. A46, C-34. Spek, A.L. (1997). HELENA, Program for Datareduction, Utrecht University, The Netherlands. Spek, A.L. (1994). Am. Crystallogr. Assoc.-Abstracts, 22, 66. Wilson, A.J.C. (1992) Ed. International Tables for Crystallography, Volume C, Kluwer Academic Publishers, Dordrecht, The Netherlands. ; _publ_section_acknowledgements ; ? ; _publ_section_figure_captions ; View of the title compound with the atom numbering scheme. Displacement ellipsoids for non-H atoms are drawn at the 50% probability level. ; #=============================================================================== data_jdu1_m _database_code_depnum_ccdc_archive 'CCDC 272916' _audit_creation_date 'May 16 13:43:39 2005' _audit_creation_method 'PLATON option' _audit_update_record ; ? ; #=============================================================================== # 5. CHEMICAL DATA _chemical_name_systematic ; (1R*,2S*,3R*,6R*,8aR*,10aR*)-2,3,6-trihydroxy-1-isopropyl-8a,10a-dimethyl- 1,2,3,6,7,8,8a,9,10,10a-decahydrobenzo[f]azulen-5-yl acetate ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C22 H34 O5' _chemical_formula_structural 'C22 H34 O5' _chemical_formula_sum 'C22 H34 O5' _chemical_formula_weight 378.49 _chemical_compound_source ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source O O 0.0106 0.0060 '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' C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' #=============================================================================== # 6. CRYSTAL DATA _symmetry_cell_setting Triclinic _symmetry_space_group_name_Hall '-P 1' _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z _cell_length_a 9.1602(16) _cell_length_b 10.6414(19) _cell_length_c 12.088(2) _cell_angle_alpha 81.181(3) _cell_angle_beta 80.027(3) _cell_angle_gamma 66.679(3) _cell_volume 1061.0(3) _cell_formula_units_Z 2 _cell_measurement_temperature 292(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _cell_special_details ; ? ; _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.49 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.10 _exptl_crystal_size_rad ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.185 _exptl_crystal_density_method 'Not Measured' _exptl_crystal_F_000 412 _exptl_absorpt_coefficient_mu 0.082 _exptl_crystal_density_meas_temp ? # Permitted for _exptl_absorpt_correction_type : # analytical 'analytical from crystal shape' # cylinder 'cylindrical' # empirical 'empirical from intensities' # gaussian 'Gaussian from crystal shape' # integration 'integration from crystal shape' # multi-scan 'symmetry-related measurements' # none 'no absorption corr. applied' # numerical 'numerical from crystal shape' # psi-scan 'psi-scan corrections' # refdelf 'refined from delta-F' # sphere 'spherical' _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SADABS; Sheldrick, 1996)' _exptl_absorpt_correction_T_min 0.9518 _exptl_absorpt_correction_T_max 0.9918 #=============================================================================== # 7. EXPERIMENTAL DATA _exptl_special_details ; ? ; _diffrn_ambient_temperature 292(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l ? ? ? _diffrn_reflns_number 10617 _diffrn_reflns_av_R_equivalents 0.0202 _diffrn_reflns_av_sigmaI/netI 0.0267 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.72 _diffrn_reflns_theta_max 25.40 _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 25.40 _diffrn_measured_fraction_theta_full 0.996 _diffrn_reflns_reduction_process ; ? ; _reflns_number_total 3891 _reflns_number_gt 3172 _reflns_threshold_expression I>2sigma(I) _computing_data_collection 'SMART (Bruker, 1998)' _computing_cell_refinement 'SAINT (Bruker, 1998)' _computing_data_reduction SAINT _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'PLATON (Spek, 2003)' #=============================================================================== # 8. REFINEMENT DATA _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^)+(0.0622P)^2^+0.2425P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3891 _refine_ls_number_parameters 252 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0703 _refine_ls_R_factor_gt 0.0550 _refine_ls_wR_factor_ref 0.1328 _refine_ls_wR_factor_gt 0.1264 _refine_ls_goodness_of_fit_ref 1.102 _refine_ls_restrained_S_all 1.102 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.268 _refine_diff_density_min -0.134 _refine_diff_density_rms 0.037 #=============================================================================== # 9. ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS 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 0.42532(17) 0.14576(13) 0.10165(11) 0.0447(4) Uani 1 1 d . . . H1 H 0.4574 0.1546 0.0344 0.067 Uiso 1 1 calc R . . O3 O 0.47304(19) 0.85908(13) 0.12726(11) 0.0492(4) Uani 1 1 d . . . H3 H 0.4371 0.9410 0.1368 0.074 Uiso 1 1 calc R . . O2 O 0.15739(19) 0.10130(14) 0.21174(12) 0.0484(4) Uani 1 1 d . . . H2 H 0.1267 0.1086 0.1504 0.073 Uiso 1 1 calc R . . O4 O 0.08428(17) 0.81146(15) 0.15354(12) 0.0505(4) Uani 1 1 d . . . C1 C 0.3323(2) 0.36179(17) 0.18599(14) 0.0291(4) Uani 1 1 d . . . C2 C 0.4364(2) 0.54864(18) 0.18061(14) 0.0307(4) Uani 1 1 d . . . C3 C 0.3023(2) 0.33676(17) 0.31414(14) 0.0311(4) Uani 1 1 d . . . C4 C 0.3639(2) 0.68528(18) 0.16072(14) 0.0344(4) Uani 1 1 d . . . C5 C 0.5715(2) 0.48073(19) 0.25503(15) 0.0349(4) Uani 1 1 d . . . C6 C 0.2880(2) 0.26572(18) 0.13059(15) 0.0338(4) Uani 1 1 d . . . H6 H 0.2320 0.3129 0.0649 0.041 Uiso 1 1 calc R . . C7 C 0.2578(2) 0.20714(18) 0.32989(15) 0.0342(4) Uani 1 1 d . . . H7 H 0.3596 0.1283 0.3206 0.041 Uiso 1 1 calc R . . C8 C 0.3870(2) 0.45446(17) 0.12928(14) 0.0316(4) Uani 1 1 d . . . H8 H 0.3954 0.4615 0.0510 0.038 Uiso 1 1 calc R . . C9 C 0.4534(2) 0.30340(19) 0.36960(15) 0.0377(4) Uani 1 1 d . . . H9A H 0.4342 0.2684 0.4474 0.045 Uiso 1 1 calc R . . H9B H 0.5397 0.2295 0.3322 0.045 Uiso 1 1 calc R . . C10 C 0.3972(2) 0.78819(19) 0.21484(15) 0.0394(5) Uani 1 1 d . . . H10 H 0.2949 0.8552 0.2460 0.047 Uiso 1 1 calc R . . C11 C 0.1779(2) 0.22319(18) 0.22513(15) 0.0356(4) Uani 1 1 d . . . H11 H 0.0727 0.2986 0.2321 0.043 Uiso 1 1 calc R . . C12 C 0.1637(2) 0.46321(19) 0.36091(17) 0.0426(5) Uani 1 1 d . . . H12A H 0.1465 0.4484 0.4417 0.064 Uiso 1 1 calc R . . H12B H 0.0680 0.4770 0.3303 0.064 Uiso 1 1 calc R . . H12C H 0.1904 0.5430 0.3399 0.064 Uiso 1 1 calc R . . C13 C 0.6337(3) 0.5888(2) 0.27597(18) 0.0451(5) Uani 1 1 d . . . H13A H 0.7023 0.5512 0.3355 0.054 Uiso 1 1 calc R . . H13B H 0.6981 0.6080 0.2080 0.054 Uiso 1 1 calc R . . C14 C 0.5005(3) 0.7218(2) 0.30891(17) 0.0460(5) Uani 1 1 d . . . H14A H 0.4352 0.7036 0.3767 0.055 Uiso 1 1 calc R . . H14B H 0.5462 0.7842 0.3251 0.055 Uiso 1 1 calc R . . C15 C 0.2360(2) 0.7488(2) 0.08466(16) 0.0440(5) Uani 1 1 d . . . H15A H 0.2590 0.8178 0.0304 0.053 Uiso 1 1 calc R . . H15B H 0.2313 0.6792 0.0437 0.053 Uiso 1 1 calc R . . C16 C 0.5120(2) 0.4194(2) 0.36945(15) 0.0390(5) Uani 1 1 d . . . H16A H 0.5986 0.3858 0.4159 0.047 Uiso 1 1 calc R . . H16B H 0.4252 0.4937 0.4061 0.047 Uiso 1 1 calc R . . C17 C 0.1711(3) 0.1764(2) 0.44577(16) 0.0447(5) Uani 1 1 d . . . H17 H 0.1984 0.2194 0.5010 0.054 Uiso 1 1 calc R . . C18 C 0.7112(2) 0.3671(2) 0.19489(18) 0.0473(5) Uani 1 1 d . . . H18A H 0.6737 0.3014 0.1764 0.071 Uiso 1 1 calc R . . H18B H 0.7931 0.3219 0.2436 0.071 Uiso 1 1 calc R . . H18C H 0.7545 0.4067 0.1270 0.071 Uiso 1 1 calc R . . O5 O -0.0387(2) 0.8594(2) 0.00091(17) 0.0846(6) Uani 1 1 d . . . C19 C -0.0445(3) 0.8643(2) 0.1002(2) 0.0589(6) Uani 1 1 d . . . C20 C -0.0110(3) 0.2329(3) 0.4541(2) 0.0629(7) Uani 1 1 d . . . H20A H -0.0426 0.1898 0.4035 0.094 Uiso 1 1 calc R . . H20B H -0.0503 0.3304 0.4340 0.094 Uiso 1 1 calc R . . H20C H -0.0548 0.2143 0.5300 0.094 Uiso 1 1 calc R . . C21 C -0.1924(3) 0.9315(4) 0.1778(3) 0.1082(12) Uani 1 1 d . . . H21A H -0.2835 0.9669 0.1368 0.162 Uiso 1 1 calc R . . H21B H -0.1829 1.0055 0.2085 0.162 Uiso 1 1 calc R . . H21C H -0.2060 0.8653 0.2380 0.162 Uiso 1 1 calc R . . C22 C 0.2340(3) 0.0218(2) 0.4808(2) 0.0688(7) Uani 1 1 d . . . H22A H 0.2108 -0.0242 0.4278 0.103 Uiso 1 1 calc R . . H22B H 0.1831 0.0047 0.5546 0.103 Uiso 1 1 calc R . . H22C H 0.3478 -0.0120 0.4819 0.103 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 0.0578(9) 0.0342(7) 0.0359(7) -0.0098(6) 0.0016(6) -0.0118(7) O3 0.0728(10) 0.0313(7) 0.0430(8) -0.0066(6) 0.0061(7) -0.0233(7) O2 0.0705(10) 0.0418(8) 0.0467(8) -0.0021(6) -0.0161(7) -0.0329(8) O4 0.0450(8) 0.0573(9) 0.0444(8) -0.0033(7) -0.0128(7) -0.0120(7) C1 0.0300(9) 0.0270(9) 0.0276(9) -0.0036(7) -0.0073(7) -0.0059(7) C2 0.0367(10) 0.0348(10) 0.0226(8) -0.0034(7) -0.0013(7) -0.0162(8) C3 0.0392(10) 0.0292(9) 0.0259(9) -0.0030(7) -0.0034(7) -0.0140(8) C4 0.0425(11) 0.0337(10) 0.0262(9) -0.0033(7) -0.0024(8) -0.0143(8) C5 0.0381(10) 0.0360(10) 0.0329(10) -0.0047(8) -0.0075(8) -0.0147(8) C6 0.0423(11) 0.0286(9) 0.0304(9) -0.0038(7) -0.0112(8) -0.0103(8) C7 0.0402(11) 0.0302(9) 0.0327(10) -0.0029(7) -0.0051(8) -0.0135(8) C8 0.0380(10) 0.0330(9) 0.0237(9) -0.0025(7) -0.0068(7) -0.0121(8) C9 0.0509(12) 0.0390(10) 0.0269(9) 0.0034(8) -0.0121(8) -0.0204(9) C10 0.0526(12) 0.0339(10) 0.0321(10) -0.0061(8) 0.0004(9) -0.0180(9) C11 0.0420(11) 0.0299(9) 0.0392(10) -0.0048(8) -0.0091(8) -0.0158(8) C12 0.0508(12) 0.0373(11) 0.0385(11) -0.0093(8) 0.0021(9) -0.0164(9) C13 0.0497(12) 0.0508(12) 0.0440(12) -0.0008(9) -0.0148(9) -0.0264(10) C14 0.0685(14) 0.0431(11) 0.0386(11) -0.0072(9) -0.0101(10) -0.0312(11) C15 0.0564(13) 0.0364(11) 0.0332(10) -0.0042(8) -0.0077(9) -0.0100(9) C16 0.0489(12) 0.0424(11) 0.0311(10) -0.0012(8) -0.0139(9) -0.0202(9) C17 0.0623(14) 0.0469(12) 0.0328(10) -0.0023(9) -0.0008(9) -0.0317(11) C18 0.0400(11) 0.0507(12) 0.0480(12) -0.0089(10) -0.0084(9) -0.0111(10) O5 0.0885(14) 0.0941(14) 0.0784(14) -0.0039(11) -0.0497(11) -0.0277(11) C19 0.0572(15) 0.0596(15) 0.0672(16) 0.0071(12) -0.0301(13) -0.0254(12) C20 0.0629(16) 0.0700(16) 0.0573(14) -0.0066(12) 0.0140(12) -0.0353(13) C21 0.0485(17) 0.142(3) 0.112(3) 0.005(2) -0.0154(18) -0.0156(18) C22 0.095(2) 0.0562(15) 0.0525(14) 0.0145(11) -0.0041(14) -0.0353(14) #=============================================================================== # 10. MOLECULAR GEOMETRY _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 C6 1.431(2) . ? O1 H1 0.8200 . ? O3 C10 1.445(2) . ? O3 H3 0.8200 . ? O2 C11 1.418(2) . ? O2 H2 0.8200 . ? O4 C19 1.323(3) . ? O4 C15 1.451(2) . ? C1 C8 1.326(2) . ? C1 C6 1.514(2) . ? C1 C3 1.526(2) . ? C2 C4 1.340(2) . ? C2 C8 1.497(2) . ? C2 C5 1.530(2) . ? C3 C9 1.533(2) . ? C3 C12 1.541(2) . ? C3 C7 1.563(2) . ? C4 C15 1.493(3) . ? C4 C10 1.508(3) . ? C5 C18 1.534(3) . ? C5 C13 1.539(3) . ? C5 C16 1.542(3) . ? C6 C11 1.527(3) . ? C6 H6 0.9800 . ? C7 C11 1.524(2) . ? C7 C17 1.543(3) . ? C7 H7 0.9800 . ? C8 H8 0.9300 . ? C9 C16 1.529(3) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 C14 1.512(3) . ? C10 H10 0.9800 . ? C11 H11 0.9800 . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? C13 C14 1.513(3) . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? C17 C20 1.523(3) . ? C17 C22 1.529(3) . ? C17 H17 0.9800 . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? O5 C19 1.201(3) . ? C19 C21 1.491(4) . ? C20 H20A 0.9600 . ? C20 H20B 0.9600 . ? C20 H20C 0.9600 . ? C21 H21A 0.9600 . ? C21 H21B 0.9600 . ? C21 H21C 0.9600 . ? C22 H22A 0.9600 . ? C22 H22B 0.9600 . ? C22 H22C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C6 O1 H1 109.5 . . ? C10 O3 H3 109.5 . . ? C11 O2 H2 109.5 . . ? C19 O4 C15 116.21(18) . . ? C8 C1 C6 123.83(16) . . ? C8 C1 C3 126.11(15) . . ? C6 C1 C3 110.06(14) . . ? C4 C2 C8 120.41(16) . . ? C4 C2 C5 122.91(16) . . ? C8 C2 C5 116.67(15) . . ? C1 C3 C9 111.93(15) . . ? C1 C3 C12 109.43(14) . . ? C9 C3 C12 110.94(15) . . ? C1 C3 C7 102.42(13) . . ? C9 C3 C7 109.50(14) . . ? C12 C3 C7 112.36(15) . . ? C2 C4 C15 121.79(17) . . ? C2 C4 C10 124.25(17) . . ? C15 C4 C10 113.92(16) . . ? C2 C5 C18 110.01(15) . . ? C2 C5 C13 109.24(15) . . ? C18 C5 C13 107.91(16) . . ? C2 C5 C16 111.01(15) . . ? C18 C5 C16 109.57(16) . . ? C13 C5 C16 109.04(15) . . ? O1 C6 C1 111.36(15) . . ? O1 C6 C11 108.58(14) . . ? C1 C6 C11 102.28(14) . . ? O1 C6 H6 111.4 . . ? C1 C6 H6 111.4 . . ? C11 C6 H6 111.4 . . ? C11 C7 C17 118.19(16) . . ? C11 C7 C3 102.91(14) . . ? C17 C7 C3 117.08(14) . . ? C11 C7 H7 105.9 . . ? C17 C7 H7 105.9 . . ? C3 C7 H7 105.9 . . ? C1 C8 C2 125.53(16) . . ? C1 C8 H8 117.2 . . ? C2 C8 H8 117.2 . . ? C16 C9 C3 117.81(15) . . ? C16 C9 H9A 107.9 . . ? C3 C9 H9A 107.9 . . ? C16 C9 H9B 107.9 . . ? C3 C9 H9B 107.9 . . ? H9A C9 H9B 107.2 . . ? O3 C10 C4 107.60(14) . . ? O3 C10 C14 110.93(17) . . ? C4 C10 C14 112.50(15) . . ? O3 C10 H10 108.6 . . ? C4 C10 H10 108.6 . . ? C14 C10 H10 108.6 . . ? O2 C11 C7 111.52(14) . . ? O2 C11 C6 115.07(15) . . ? C7 C11 C6 103.15(14) . . ? O2 C11 H11 109.0 . . ? C7 C11 H11 109.0 . . ? C6 C11 H11 109.0 . . ? C3 C12 H12A 109.5 . . ? C3 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C3 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C14 C13 C5 112.97(17) . . ? C14 C13 H13A 109.0 . . ? C5 C13 H13A 109.0 . . ? C14 C13 H13B 109.0 . . ? C5 C13 H13B 109.0 . . ? H13A C13 H13B 107.8 . . ? C10 C14 C13 110.51(16) . . ? C10 C14 H14A 109.5 . . ? C13 C14 H14A 109.5 . . ? C10 C14 H14B 109.5 . . ? C13 C14 H14B 109.5 . . ? H14A C14 H14B 108.1 . . ? O4 C15 C4 108.19(15) . . ? O4 C15 H15A 110.1 . . ? C4 C15 H15A 110.1 . . ? O4 C15 H15B 110.1 . . ? C4 C15 H15B 110.1 . . ? H15A C15 H15B 108.4 . . ? C9 C16 C5 118.21(15) . . ? C9 C16 H16A 107.8 . . ? C5 C16 H16A 107.8 . . ? C9 C16 H16B 107.8 . . ? C5 C16 H16B 107.8 . . ? H16A C16 H16B 107.1 . . ? C20 C17 C22 109.68(19) . . ? C20 C17 C7 115.21(17) . . ? C22 C17 C7 110.42(17) . . ? C20 C17 H17 107.0 . . ? C22 C17 H17 107.0 . . ? C7 C17 H17 107.0 . . ? C5 C18 H18A 109.5 . . ? C5 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C5 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? O5 C19 O4 122.7(2) . . ? O5 C19 C21 125.5(2) . . ? O4 C19 C21 111.7(2) . . ? C17 C20 H20A 109.5 . . ? C17 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C17 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C19 C21 H21A 109.5 . . ? C19 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C19 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C17 C22 H22A 109.5 . . ? C17 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C17 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C8 C1 C3 C9 -56.8(2) . . . . ? C6 C1 C3 C9 123.98(16) . . . . ? C8 C1 C3 C12 66.6(2) . . . . ? C6 C1 C3 C12 -112.61(16) . . . . ? C8 C1 C3 C7 -174.04(17) . . . . ? C6 C1 C3 C7 6.78(18) . . . . ? C8 C2 C4 C15 -1.9(3) . . . . ? C5 C2 C4 C15 177.94(16) . . . . ? C8 C2 C4 C10 175.58(16) . . . . ? C5 C2 C4 C10 -4.5(3) . . . . ? C4 C2 C5 C18 -131.96(19) . . . . ? C8 C2 C5 C18 47.9(2) . . . . ? C4 C2 C5 C13 -13.7(2) . . . . ? C8 C2 C5 C13 166.20(15) . . . . ? C4 C2 C5 C16 106.59(19) . . . . ? C8 C2 C5 C16 -73.53(19) . . . . ? C8 C1 C6 O1 84.7(2) . . . . ? C3 C1 C6 O1 -96.10(17) . . . . ? C8 C1 C6 C11 -159.51(17) . . . . ? C3 C1 C6 C11 19.70(18) . . . . ? C1 C3 C7 C11 -30.76(17) . . . . ? C9 C3 C7 C11 -149.68(15) . . . . ? C12 C3 C7 C11 86.55(17) . . . . ? C1 C3 C7 C17 -162.17(16) . . . . ? C9 C3 C7 C17 78.9(2) . . . . ? C12 C3 C7 C17 -44.9(2) . . . . ? C6 C1 C8 C2 -178.23(17) . . . . ? C3 C1 C8 C2 2.7(3) . . . . ? C4 C2 C8 C1 -120.9(2) . . . . ? C5 C2 C8 C1 59.2(2) . . . . ? C1 C3 C9 C16 70.5(2) . . . . ? C12 C3 C9 C16 -52.0(2) . . . . ? C7 C3 C9 C16 -176.63(16) . . . . ? C2 C4 C10 O3 112.8(2) . . . . ? C15 C4 C10 O3 -69.5(2) . . . . ? C2 C4 C10 C14 -9.7(3) . . . . ? C15 C4 C10 C14 167.99(17) . . . . ? C17 C7 C11 O2 -61.2(2) . . . . ? C3 C7 C11 O2 168.05(15) . . . . ? C17 C7 C11 C6 174.75(15) . . . . ? C3 C7 C11 C6 44.01(17) . . . . ? O1 C6 C11 O2 -42.9(2) . . . . ? C1 C6 C11 O2 -160.71(15) . . . . ? O1 C6 C11 C7 78.78(16) . . . . ? C1 C6 C11 C7 -39.02(17) . . . . ? C2 C5 C13 C14 46.6(2) . . . . ? C18 C5 C13 C14 166.16(16) . . . . ? C16 C5 C13 C14 -74.9(2) . . . . ? O3 C10 C14 C13 -79.09(19) . . . . ? C4 C10 C14 C13 41.5(2) . . . . ? C5 C13 C14 C10 -62.3(2) . . . . ? C19 O4 C15 C4 -175.28(17) . . . . ? C2 C4 C15 O4 109.3(2) . . . . ? C10 C4 C15 O4 -68.4(2) . . . . ? C3 C9 C16 C5 -65.3(2) . . . . ? C2 C5 C16 C9 63.1(2) . . . . ? C18 C5 C16 C9 -58.7(2) . . . . ? C13 C5 C16 C9 -176.55(16) . . . . ? C11 C7 C17 C20 -29.3(2) . . . . ? C3 C7 C17 C20 94.7(2) . . . . ? C11 C7 C17 C22 95.6(2) . . . . ? C3 C7 C17 C22 -140.41(19) . . . . ? C15 O4 C19 O5 1.3(3) . . . . ? C15 O4 C19 C21 -177.4(2) . . . . ? # End of Crystallographic Information File