data_rac-VAPOL _publ_requested_journal J.Org.Chem. _publ_contact_author_name 'Adam J. Matzger' _publ_contact_author_address ;Department of Chemistry and the Macromolecular Science and Engineering Program, University of Michigan, Ann Arbor, Michigan 48109-1055, USA ; _publ_contact_author_email matzger@umich.edu _publ_contact_author_phone (734)-615-6627 _publ_contact_author_fax (734)-615-8553 loop_ _publ_author_name _publ_author_address 'Matzger, Adam J.' ;Department of Chemistry and the Macromolecular Science and Engineering Program, University of Michigan, Ann Arbor, Michigan 48109-1055, USA ; 'Price, Christopher P.' ;Department of Chemistry, University of Michigan, Ann Arbor, Michigan 48109-1055, USA ; _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common VAPOL _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C40 H26 O2' _chemical_formula_weight 538.61 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.7591(9) _cell_length_b 11.4941(10) _cell_length_c 13.7768(12) _cell_angle_alpha 78.3890(10) _cell_angle_beta 83.621(2) _cell_angle_gamma 65.8440(10) _cell_volume 1380.5(2) _cell_formula_units_Z 2 _cell_measurement_temperature 153(2) _cell_measurement_reflns_used 4341 _cell_measurement_theta_min 2.29 _cell_measurement_theta_max 27.50 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.075 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.296 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 564 _exptl_absorpt_coefficient_mu 0.078 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 153(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11947 _diffrn_reflns_av_R_equivalents 0.0317 _diffrn_reflns_av_sigmaI/netI 0.0739 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.51 _diffrn_reflns_theta_max 27.53 _reflns_number_total 6139 _reflns_number_gt 3755 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0314P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6139 _refine_ls_number_parameters 381 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0800 _refine_ls_R_factor_gt 0.0440 _refine_ls_wR_factor_ref 0.0858 _refine_ls_wR_factor_gt 0.0774 _refine_ls_goodness_of_fit_ref 0.847 _refine_ls_restrained_S_all 0.847 _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 0.90692(11) 0.38574(10) 0.24047(8) 0.0281(3) Uani 1 1 d . . . H1A H 0.9159 0.3126 0.2722 0.042 Uiso 1 1 calc R . . O2 O 0.83238(12) 0.33946(9) 0.47366(8) 0.0270(3) Uani 1 1 d . . . H2A H 0.7861 0.4140 0.4420 0.041 Uiso 1 1 calc R . . C33 C 0.87718(16) 0.09881(14) 0.60770(11) 0.0207(3) Uani 1 1 d . . . C23 C 0.71145(16) 0.28975(14) 0.35635(10) 0.0192(3) Uani 1 1 d . . . C25 C 0.93600(16) 0.17251(14) 0.64756(11) 0.0242(4) Uani 1 1 d . . . H25 H 0.9388 0.2495 0.6080 0.029 Uiso 1 1 calc R . . C3 C 0.65979(16) 0.42822(14) 0.30654(10) 0.0195(3) Uani 1 1 d . . . C12 C 0.72188(17) 0.60427(14) 0.20423(11) 0.0216(4) Uani 1 1 d . . . C13 C 0.82364(17) 0.65615(15) 0.14286(11) 0.0230(4) Uani 1 1 d . . . C31 C 0.75927(16) 0.05125(14) 0.47815(11) 0.0225(4) Uani 1 1 d . . . C24 C 0.78716(16) 0.25378(14) 0.44463(11) 0.0201(3) Uani 1 1 d . . . C32 C 0.81243(16) 0.13465(14) 0.50983(11) 0.0202(3) Uani 1 1 d . . . C4 C 0.76142(16) 0.47328(14) 0.25110(11) 0.0210(4) Uani 1 1 d . . . C22 C 0.66563(16) 0.20101(14) 0.32511(11) 0.0219(4) Uani 1 1 d . . . C15 C 0.39262(16) 0.46800(14) 0.37014(11) 0.0223(4) Uani 1 1 d . . . C14 C 0.76654(18) 0.79102(15) 0.10360(11) 0.0253(4) Uani 1 1 d . . . C11 C 0.56952(17) 0.68901(15) 0.21845(11) 0.0243(4) Uani 1 1 d . . . C1 C 0.46617(17) 0.64157(15) 0.27210(11) 0.0250(4) Uani 1 1 d . . . H1 H 0.3644 0.6998 0.2783 0.030 Uiso 1 1 calc R . . C2 C 0.50730(17) 0.51375(14) 0.31591(11) 0.0215(4) Uani 1 1 d . . . C29 C 0.82749(17) -0.09966(14) 0.63260(12) 0.0266(4) Uani 1 1 d . . . H29 H 0.8323 -0.1783 0.6735 0.032 Uiso 1 1 calc R . . C34 C 0.87972(16) -0.01754(14) 0.66901(11) 0.0232(4) Uani 1 1 d . . . C5 C 0.97396(18) 0.58089(16) 0.11731(11) 0.0292(4) Uani 1 1 d . . . H5 H 1.0149 0.4904 0.1417 0.035 Uiso 1 1 calc R . . C35 C 0.58707(17) 0.23503(14) 0.23040(11) 0.0234(4) Uani 1 1 d . . . C21 C 0.69155(16) 0.08427(14) 0.38602(11) 0.0239(4) Uani 1 1 d . . . H21 H 0.6628 0.0237 0.3653 0.029 Uiso 1 1 calc R . . C28 C 0.93397(18) -0.05178(15) 0.76593(12) 0.0297(4) Uani 1 1 d . . . H28 H 0.9335 -0.1288 0.8068 0.036 Uiso 1 1 calc R . . C8 C 0.85985(19) 0.84366(16) 0.04218(11) 0.0310(4) Uani 1 1 d . . . H8 H 0.8209 0.9335 0.0156 0.037 Uiso 1 1 calc R . . C30 C 0.77170(17) -0.06759(14) 0.54154(12) 0.0273(4) Uani 1 1 d . . . H30 H 0.7399 -0.1250 0.5188 0.033 Uiso 1 1 calc R . . C20 C 0.25977(17) 0.49743(15) 0.32389(12) 0.0275(4) Uani 1 1 d . . . H20 H 0.2439 0.5452 0.2584 0.033 Uiso 1 1 calc R . . C9 C 0.61463(19) 0.87298(16) 0.12495(12) 0.0326(4) Uani 1 1 d . . . H9 H 0.5795 0.9634 0.1007 0.039 Uiso 1 1 calc R . . C17 C 0.30362(18) 0.35718(15) 0.51490(12) 0.0303(4) Uani 1 1 d . . . H17 H 0.3190 0.3089 0.5803 0.036 Uiso 1 1 calc R . . C10 C 0.52081(19) 0.82421(15) 0.17869(12) 0.0316(4) Uani 1 1 d . . . H10 H 0.4198 0.8807 0.1906 0.038 Uiso 1 1 calc R . . C16 C 0.41305(17) 0.39736(14) 0.46629(11) 0.0250(4) Uani 1 1 d . . . H16 H 0.5031 0.3765 0.4989 0.030 Uiso 1 1 calc R . . C26 C 0.98901(18) 0.13571(15) 0.74164(12) 0.0303(4) Uani 1 1 d . . . H26 H 1.0277 0.1875 0.7661 0.036 Uiso 1 1 calc R . . C7 C 1.00550(19) 0.76766(16) 0.02014(12) 0.0339(4) Uani 1 1 d . . . H7 H 1.0675 0.8047 -0.0207 0.041 Uiso 1 1 calc R . . C40 C 0.45822(18) 0.21224(16) 0.22822(12) 0.0314(4) Uani 1 1 d . . . H40 H 0.4217 0.1737 0.2872 0.038 Uiso 1 1 calc R . . C19 C 0.15007(18) 0.45719(16) 0.37310(13) 0.0331(4) Uani 1 1 d . . . H19 H 0.0597 0.4780 0.3410 0.040 Uiso 1 1 calc R . . C18 C 0.17159(18) 0.38748(15) 0.46803(13) 0.0328(4) Uani 1 1 d . . . H18 H 0.0963 0.3603 0.5013 0.039 Uiso 1 1 calc R . . C6 C 1.06235(19) 0.63564(16) 0.05792(12) 0.0337(4) Uani 1 1 d . . . H6 H 1.1634 0.5828 0.0425 0.040 Uiso 1 1 calc R . . C36 C 0.63861(18) 0.29010(15) 0.14236(12) 0.0306(4) Uani 1 1 d . . . H36 H 0.7270 0.3057 0.1421 0.037 Uiso 1 1 calc R . . C27 C 0.98704(19) 0.02358(16) 0.80198(12) 0.0335(4) Uani 1 1 d . . . H27 H 1.0223 -0.0002 0.8676 0.040 Uiso 1 1 calc R . . C37 C 0.5628(2) 0.32243(17) 0.05515(12) 0.0376(5) Uani 1 1 d . . . H37 H 0.5997 0.3595 -0.0043 0.045 Uiso 1 1 calc R . . C39 C 0.38224(19) 0.24514(17) 0.14088(13) 0.0373(5) Uani 1 1 d . . . H39 H 0.2942 0.2292 0.1405 0.045 Uiso 1 1 calc R . . C38 C 0.4338(2) 0.30079(17) 0.05465(13) 0.0392(5) Uani 1 1 d . . . H38 H 0.3809 0.3241 -0.0048 0.047 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 0.0215(6) 0.0216(6) 0.0359(7) 0.0017(5) 0.0017(5) -0.0071(5) O2 0.0353(7) 0.0190(6) 0.0293(7) 0.0012(5) -0.0106(5) -0.0135(5) C33 0.0164(8) 0.0192(8) 0.0234(9) -0.0030(7) 0.0018(7) -0.0049(7) C23 0.0167(8) 0.0204(8) 0.0194(8) -0.0017(7) 0.0014(6) -0.0076(7) C25 0.0264(9) 0.0205(8) 0.0252(9) -0.0009(7) -0.0013(7) -0.0100(7) C3 0.0213(8) 0.0214(8) 0.0175(8) -0.0015(7) -0.0037(7) -0.0103(7) C12 0.0244(9) 0.0233(9) 0.0186(8) -0.0022(7) -0.0021(7) -0.0113(7) C13 0.0287(9) 0.0263(9) 0.0171(8) -0.0004(7) -0.0043(7) -0.0145(8) C31 0.0210(9) 0.0203(8) 0.0257(9) -0.0041(7) 0.0017(7) -0.0083(7) C24 0.0184(8) 0.0197(8) 0.0245(9) -0.0064(7) 0.0029(7) -0.0094(7) C32 0.0168(8) 0.0203(8) 0.0222(8) -0.0047(7) 0.0028(7) -0.0065(7) C4 0.0196(9) 0.0209(8) 0.0225(9) -0.0045(7) -0.0034(7) -0.0070(7) C22 0.0183(8) 0.0247(9) 0.0234(9) -0.0058(7) 0.0019(7) -0.0090(7) C15 0.0202(9) 0.0210(9) 0.0265(9) -0.0084(7) 0.0020(7) -0.0076(7) C14 0.0333(10) 0.0260(9) 0.0197(9) 0.0008(7) -0.0062(7) -0.0157(8) C11 0.0267(9) 0.0218(9) 0.0232(9) -0.0006(7) -0.0047(7) -0.0090(7) C1 0.0199(9) 0.0254(9) 0.0262(9) -0.0030(7) -0.0015(7) -0.0061(7) C2 0.0234(9) 0.0258(9) 0.0178(8) -0.0042(7) -0.0020(7) -0.0118(7) C29 0.0262(9) 0.0192(9) 0.0319(10) 0.0025(7) -0.0010(8) -0.0097(7) C34 0.0195(8) 0.0204(8) 0.0259(9) -0.0017(7) 0.0016(7) -0.0057(7) C5 0.0309(10) 0.0288(9) 0.0277(10) 0.0013(8) -0.0018(8) -0.0143(8) C35 0.0254(9) 0.0217(9) 0.0240(9) -0.0066(7) -0.0007(7) -0.0092(7) C21 0.0247(9) 0.0219(9) 0.0289(9) -0.0070(7) -0.0008(7) -0.0120(7) C28 0.0346(10) 0.0237(9) 0.0261(10) 0.0034(7) -0.0025(8) -0.0099(8) C8 0.0417(11) 0.0294(10) 0.0259(10) 0.0031(8) -0.0069(8) -0.0201(9) C30 0.0275(9) 0.0209(9) 0.0352(10) -0.0046(8) -0.0014(8) -0.0115(7) C20 0.0255(9) 0.0275(9) 0.0290(9) -0.0069(7) -0.0005(8) -0.0089(8) C9 0.0414(11) 0.0211(9) 0.0325(10) 0.0027(8) -0.0049(8) -0.0120(8) C17 0.0328(10) 0.0227(9) 0.0332(10) -0.0043(8) 0.0078(8) -0.0113(8) C10 0.0297(10) 0.0242(9) 0.0349(10) -0.0008(8) -0.0021(8) -0.0066(8) C16 0.0225(9) 0.0234(9) 0.0281(9) -0.0068(7) 0.0020(7) -0.0077(7) C26 0.0372(10) 0.0281(10) 0.0280(10) -0.0025(8) -0.0073(8) -0.0150(8) C7 0.0402(11) 0.0417(11) 0.0257(10) 0.0034(8) 0.0009(8) -0.0270(9) C40 0.0351(10) 0.0385(10) 0.0272(10) -0.0041(8) -0.0006(8) -0.0219(9) C19 0.0229(9) 0.0350(10) 0.0464(12) -0.0163(9) -0.0001(8) -0.0125(8) C18 0.0262(10) 0.0269(10) 0.0497(12) -0.0140(9) 0.0123(9) -0.0150(8) C6 0.0320(10) 0.0376(11) 0.0311(10) -0.0004(8) 0.0042(8) -0.0173(9) C36 0.0319(10) 0.0373(10) 0.0284(10) -0.0070(8) -0.0005(8) -0.0191(8) C27 0.0429(11) 0.0309(10) 0.0245(9) 0.0019(8) -0.0097(8) -0.0134(9) C37 0.0467(12) 0.0480(12) 0.0242(10) -0.0026(9) -0.0025(9) -0.0264(10) C39 0.0333(10) 0.0503(12) 0.0374(11) -0.0095(9) -0.0073(9) -0.0232(9) C38 0.0457(12) 0.0461(12) 0.0292(10) -0.0051(9) -0.0146(9) -0.0190(10) _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 C4 1.3761(16) . ? O1 H1A 0.8400 . ? O2 C24 1.3704(16) . ? O2 H2A 0.8400 . ? C33 C25 1.416(2) . ? C33 C34 1.4231(19) . ? C33 C32 1.463(2) . ? C23 C24 1.3940(19) . ? C23 C22 1.4207(19) . ? C23 C3 1.4962(19) . ? C25 C26 1.370(2) . ? C25 H25 0.9500 . ? C3 C4 1.3886(19) . ? C3 C2 1.4173(19) . ? C12 C4 1.4218(19) . ? C12 C11 1.423(2) . ? C12 C13 1.467(2) . ? C13 C5 1.412(2) . ? C13 C14 1.424(2) . ? C31 C21 1.407(2) . ? C31 C32 1.416(2) . ? C31 C30 1.432(2) . ? C24 C32 1.4214(19) . ? C22 C21 1.3729(19) . ? C22 C35 1.488(2) . ? C15 C20 1.393(2) . ? C15 C16 1.395(2) . ? C15 C2 1.492(2) . ? C14 C8 1.409(2) . ? C14 C9 1.430(2) . ? C11 C1 1.408(2) . ? C11 C10 1.432(2) . ? C1 C2 1.3777(19) . ? C1 H1 0.9500 . ? C29 C30 1.344(2) . ? C29 C34 1.430(2) . ? C29 H29 0.9500 . ? C34 C28 1.412(2) . ? C5 C6 1.375(2) . ? C5 H5 0.9500 . ? C35 C40 1.390(2) . ? C35 C36 1.393(2) . ? C21 H21 0.9500 . ? C28 C27 1.365(2) . ? C28 H28 0.9500 . ? C8 C7 1.368(2) . ? C8 H8 0.9500 . ? C30 H30 0.9500 . ? C20 C19 1.392(2) . ? C20 H20 0.9500 . ? C9 C10 1.343(2) . ? C9 H9 0.9500 . ? C17 C16 1.387(2) . ? C17 C18 1.388(2) . ? C17 H17 0.9500 . ? C10 H10 0.9500 . ? C16 H16 0.9500 . ? C26 C27 1.392(2) . ? C26 H26 0.9500 . ? C7 C6 1.392(2) . ? C7 H7 0.9500 . ? C40 C39 1.388(2) . ? C40 H40 0.9500 . ? C19 C18 1.378(2) . ? C19 H19 0.9500 . ? C18 H18 0.9500 . ? C6 H6 0.9500 . ? C36 C37 1.386(2) . ? C36 H36 0.9500 . ? C27 H27 0.9500 . ? C37 C38 1.380(2) . ? C37 H37 0.9500 . ? C39 C38 1.378(2) . ? C39 H39 0.9500 . ? C38 H38 0.9500 . ? 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 C4 O1 H1A 109.5 . . ? C24 O2 H2A 109.5 . . ? C25 C33 C34 116.81(14) . . ? C25 C33 C32 124.91(13) . . ? C34 C33 C32 118.26(14) . . ? C24 C23 C22 119.48(13) . . ? C24 C23 C3 117.91(13) . . ? C22 C23 C3 121.87(13) . . ? C26 C25 C33 121.70(14) . . ? C26 C25 H25 119.2 . . ? C33 C25 H25 119.2 . . ? C4 C3 C2 119.83(13) . . ? C4 C3 C23 119.99(13) . . ? C2 C3 C23 120.18(13) . . ? C4 C12 C11 115.62(13) . . ? C4 C12 C13 125.45(14) . . ? C11 C12 C13 118.92(13) . . ? C5 C13 C14 117.30(14) . . ? C5 C13 C12 124.51(14) . . ? C14 C13 C12 118.17(14) . . ? C21 C31 C32 121.09(14) . . ? C21 C31 C30 119.25(14) . . ? C32 C31 C30 119.65(14) . . ? O2 C24 C23 119.09(13) . . ? O2 C24 C32 117.70(13) . . ? C23 C24 C32 123.11(14) . . ? C31 C32 C24 115.61(13) . . ? C31 C32 C33 119.32(13) . . ? C24 C32 C33 124.90(14) . . ? O1 C4 C3 117.91(13) . . ? O1 C4 C12 118.84(13) . . ? C3 C4 C12 123.24(14) . . ? C21 C22 C23 118.30(14) . . ? C21 C22 C35 120.66(14) . . ? C23 C22 C35 121.02(13) . . ? C20 C15 C16 118.57(14) . . ? C20 C15 C2 119.13(14) . . ? C16 C15 C2 122.29(13) . . ? C8 C14 C13 119.75(15) . . ? C8 C14 C9 119.78(15) . . ? C13 C14 C9 120.46(14) . . ? C1 C11 C12 120.68(14) . . ? C1 C11 C10 119.54(15) . . ? C12 C11 C10 119.77(14) . . ? C2 C1 C11 122.40(14) . . ? C2 C1 H1 118.8 . . ? C11 C1 H1 118.8 . . ? C1 C2 C3 118.12(14) . . ? C1 C2 C15 120.22(14) . . ? C3 C2 C15 121.65(13) . . ? C30 C29 C34 121.17(14) . . ? C30 C29 H29 119.4 . . ? C34 C29 H29 119.4 . . ? C28 C34 C33 119.87(14) . . ? C28 C34 C29 120.02(14) . . ? C33 C34 C29 120.11(14) . . ? C6 C5 C13 121.43(15) . . ? C6 C5 H5 119.3 . . ? C13 C5 H5 119.3 . . ? C40 C35 C36 118.15(14) . . ? C40 C35 C22 119.96(14) . . ? C36 C35 C22 121.88(14) . . ? C22 C21 C31 122.22(14) . . ? C22 C21 H21 118.9 . . ? C31 C21 H21 118.9 . . ? C27 C28 C34 121.27(15) . . ? C27 C28 H28 119.4 . . ? C34 C28 H28 119.4 . . ? C7 C8 C14 121.15(15) . . ? C7 C8 H8 119.4 . . ? C14 C8 H8 119.4 . . ? C29 C30 C31 121.38(15) . . ? C29 C30 H30 119.3 . . ? C31 C30 H30 119.3 . . ? C19 C20 C15 120.38(15) . . ? C19 C20 H20 119.8 . . ? C15 C20 H20 119.8 . . ? C10 C9 C14 121.03(15) . . ? C10 C9 H9 119.5 . . ? C14 C9 H9 119.5 . . ? C16 C17 C18 119.99(16) . . ? C16 C17 H17 120.0 . . ? C18 C17 H17 120.0 . . ? C9 C10 C11 121.49(16) . . ? C9 C10 H10 119.3 . . ? C11 C10 H10 119.3 . . ? C17 C16 C15 120.83(15) . . ? C17 C16 H16 119.6 . . ? C15 C16 H16 119.6 . . ? C25 C26 C27 120.98(15) . . ? C25 C26 H26 119.5 . . ? C27 C26 H26 119.5 . . ? C8 C7 C6 119.58(15) . . ? C8 C7 H7 120.2 . . ? C6 C7 H7 120.2 . . ? C39 C40 C35 120.74(15) . . ? C39 C40 H40 119.6 . . ? C35 C40 H40 119.6 . . ? C18 C19 C20 120.49(15) . . ? C18 C19 H19 119.8 . . ? C20 C19 H19 119.8 . . ? C19 C18 C17 119.73(15) . . ? C19 C18 H18 120.1 . . ? C17 C18 H18 120.1 . . ? C5 C6 C7 120.79(16) . . ? C5 C6 H6 119.6 . . ? C7 C6 H6 119.6 . . ? C37 C36 C35 120.98(15) . . ? C37 C36 H36 119.5 . . ? C35 C36 H36 119.5 . . ? C28 C27 C26 119.33(15) . . ? C28 C27 H27 120.3 . . ? C26 C27 H27 120.3 . . ? C38 C37 C36 120.09(16) . . ? C38 C37 H37 120.0 . . ? C36 C37 H37 120.0 . . ? C38 C39 C40 120.38(16) . . ? C38 C39 H39 119.8 . . ? C40 C39 H39 119.8 . . ? C39 C38 C37 119.65(16) . . ? C39 C38 H38 120.2 . . ? C37 C38 H38 120.2 . . ? 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 C34 C33 C25 C26 -1.8(2) . . . . ? C32 C33 C25 C26 177.11(15) . . . . ? C24 C23 C3 C4 78.59(18) . . . . ? C22 C23 C3 C4 -111.37(17) . . . . ? C24 C23 C3 C2 -101.30(17) . . . . ? C22 C23 C3 C2 68.75(19) . . . . ? C4 C12 C13 C5 3.7(2) . . . . ? C11 C12 C13 C5 -175.36(15) . . . . ? C4 C12 C13 C14 -178.27(15) . . . . ? C11 C12 C13 C14 2.7(2) . . . . ? C22 C23 C24 O2 179.30(13) . . . . ? C3 C23 C24 O2 -10.4(2) . . . . ? C22 C23 C24 C32 -4.6(2) . . . . ? C3 C23 C24 C32 165.70(13) . . . . ? C21 C31 C32 C24 2.4(2) . . . . ? C30 C31 C32 C24 -176.36(13) . . . . ? C21 C31 C32 C33 177.79(13) . . . . ? C30 C31 C32 C33 -1.0(2) . . . . ? O2 C24 C32 C31 177.96(13) . . . . ? C23 C24 C32 C31 1.8(2) . . . . ? O2 C24 C32 C33 2.8(2) . . . . ? C23 C24 C32 C33 -173.32(14) . . . . ? C25 C33 C32 C31 179.11(14) . . . . ? C34 C33 C32 C31 -2.0(2) . . . . ? C25 C33 C32 C24 -5.9(2) . . . . ? C34 C33 C32 C24 172.94(14) . . . . ? C2 C3 C4 O1 -177.30(13) . . . . ? C23 C3 C4 O1 2.8(2) . . . . ? C2 C3 C4 C12 1.9(2) . . . . ? C23 C3 C4 C12 -177.98(14) . . . . ? C11 C12 C4 O1 179.93(13) . . . . ? C13 C12 C4 O1 0.8(2) . . . . ? C11 C12 C4 C3 0.7(2) . . . . ? C13 C12 C4 C3 -178.35(14) . . . . ? C24 C23 C22 C21 3.1(2) . . . . ? C3 C23 C22 C21 -166.80(14) . . . . ? C24 C23 C22 C35 -178.87(14) . . . . ? C3 C23 C22 C35 11.2(2) . . . . ? C5 C13 C14 C8 -0.1(2) . . . . ? C12 C13 C14 C8 -178.31(14) . . . . ? C5 C13 C14 C9 178.99(14) . . . . ? C12 C13 C14 C9 0.8(2) . . . . ? C4 C12 C11 C1 -2.8(2) . . . . ? C13 C12 C11 C1 176.36(14) . . . . ? C4 C12 C11 C10 176.61(14) . . . . ? C13 C12 C11 C10 -4.2(2) . . . . ? C12 C11 C1 C2 2.3(2) . . . . ? C10 C11 C1 C2 -177.09(15) . . . . ? C11 C1 C2 C3 0.4(2) . . . . ? C11 C1 C2 C15 -178.72(14) . . . . ? C4 C3 C2 C1 -2.5(2) . . . . ? C23 C3 C2 C1 177.42(13) . . . . ? C4 C3 C2 C15 176.66(14) . . . . ? C23 C3 C2 C15 -3.5(2) . . . . ? C20 C15 C2 C1 50.4(2) . . . . ? C16 C15 C2 C1 -129.04(16) . . . . ? C20 C15 C2 C3 -128.69(16) . . . . ? C16 C15 C2 C3 51.9(2) . . . . ? C25 C33 C34 C28 2.3(2) . . . . ? C32 C33 C34 C28 -176.64(14) . . . . ? C25 C33 C34 C29 -177.67(13) . . . . ? C32 C33 C34 C29 3.4(2) . . . . ? C30 C29 C34 C28 178.27(15) . . . . ? C30 C29 C34 C33 -1.7(2) . . . . ? C14 C13 C5 C6 0.8(2) . . . . ? C12 C13 C5 C6 178.82(15) . . . . ? C21 C22 C35 C40 45.1(2) . . . . ? C23 C22 C35 C40 -132.87(16) . . . . ? C21 C22 C35 C36 -135.03(16) . . . . ? C23 C22 C35 C36 47.0(2) . . . . ? C23 C22 C21 C31 1.0(2) . . . . ? C35 C22 C21 C31 -177.04(14) . . . . ? C32 C31 C21 C22 -3.9(2) . . . . ? C30 C31 C21 C22 174.89(15) . . . . ? C33 C34 C28 C27 -1.2(2) . . . . ? C29 C34 C28 C27 178.81(15) . . . . ? C13 C14 C8 C7 -0.7(2) . . . . ? C9 C14 C8 C7 -179.78(15) . . . . ? C34 C29 C30 C31 -1.4(2) . . . . ? C21 C31 C30 C29 -176.05(14) . . . . ? C32 C31 C30 C29 2.7(2) . . . . ? C16 C15 C20 C19 0.2(2) . . . . ? C2 C15 C20 C19 -179.31(14) . . . . ? C8 C14 C9 C10 176.26(15) . . . . ? C13 C14 C9 C10 -2.9(2) . . . . ? C14 C9 C10 C11 1.3(3) . . . . ? C1 C11 C10 C9 -178.28(15) . . . . ? C12 C11 C10 C9 2.3(2) . . . . ? C18 C17 C16 C15 -0.2(2) . . . . ? C20 C15 C16 C17 0.0(2) . . . . ? C2 C15 C16 C17 179.48(14) . . . . ? C33 C25 C26 C27 0.0(2) . . . . ? C14 C8 C7 C6 0.8(2) . . . . ? C36 C35 C40 C39 -0.8(2) . . . . ? C22 C35 C40 C39 179.03(15) . . . . ? C15 C20 C19 C18 -0.2(2) . . . . ? C20 C19 C18 C17 0.0(2) . . . . ? C16 C17 C18 C19 0.2(2) . . . . ? C13 C5 C6 C7 -0.6(2) . . . . ? C8 C7 C6 C5 -0.2(3) . . . . ? C40 C35 C36 C37 0.6(2) . . . . ? C22 C35 C36 C37 -179.27(15) . . . . ? C34 C28 C27 C26 -0.6(3) . . . . ? C25 C26 C27 C28 1.2(3) . . . . ? C35 C36 C37 C38 0.3(3) . . . . ? C35 C40 C39 C38 0.2(3) . . . . ? C40 C39 C38 C37 0.7(3) . . . . ? C36 C37 C38 C39 -1.0(3) . . . . ? _diffrn_measured_fraction_theta_max 0.964 _diffrn_reflns_theta_full 27.53 _diffrn_measured_fraction_theta_full 0.964 _refine_diff_density_max 0.250 _refine_diff_density_min -0.175 _refine_diff_density_rms 0.038