# Supplementary Material (ESI) for Perkin Transactions # This journal is © The Royal Society of Chemistry 2002 data_global _journal_coden_Cambridge 207 loop_ _publ_author_name 'Maskill, H.' 'Carey, Kieran A.' 'Clegg, William' 'Elsegood, Mark R. J.' 'Golding, Bernard T.' 'Hill, M. N. Stuart' _publ_contact_author_name 'Dr H Maskill' _publ_contact_author_address ; Department of Chemistry University of Newcastle Bedson Building NEWCASTLE-UPON-TYNE NE1 7RU UK ; _publ_contact_author_email 'H.MASKILL@NCL.AC.UK' _publ_requested_journal 'Perkin Transactions 1' _publ_section_title ; Synthesis of highly hindered oxepins and an azepine from bis-trityl carbenium ions: structural characterisation by NMR and X-ray crystallography ; data_hm13 _database_code_CSD 190257 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C45 H36 O' _chemical_formula_weight 592.74 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0181 0.0091 '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' 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P2(1)/n 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' _cell_length_a 13.6161(18) _cell_length_b 14.295(2) _cell_length_c 16.520(2) _cell_angle_alpha 90.00 _cell_angle_beta 95.178(18) _cell_angle_gamma 90.00 _cell_volume 3202.2(8) _cell_formula_units_Z 4 _cell_measurement_temperature 160(2) _cell_measurement_reflns_used 43 _cell_measurement_theta_min 20.05 _cell_measurement_theta_max 24.59 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.38 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.229 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1256 _exptl_absorpt_coefficient_mu 0.546 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.690 _exptl_absorpt_correction_T_max 0.974 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 160(2) _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Stoe-Siemens diffractometer' _diffrn_measurement_method '\w/\q scans with on-line profile fitting' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 5 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 60 _diffrn_standards_decay_% 5.0 _diffrn_reflns_number 8465 _diffrn_reflns_av_R_equivalents 0.0470 _diffrn_reflns_av_sigmaI/netI 0.0527 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 4.03 _diffrn_reflns_theta_max 67.53 _reflns_number_total 5563 _reflns_number_gt 4328 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Stoe DIF4' _computing_cell_refinement 'Stoe DIF4' _computing_data_reduction 'local programs' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Siemens SHELXTL' _computing_publication_material 'SHELXTL and local programs' _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^)+(0.0674P)^2^+1.4782P] 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 SHELXL _refine_ls_extinction_coef 0.00082(15) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 5563 _refine_ls_number_parameters 417 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0720 _refine_ls_R_factor_gt 0.0533 _refine_ls_wR_factor_ref 0.1500 _refine_ls_wR_factor_gt 0.1320 _refine_ls_goodness_of_fit_ref 1.054 _refine_ls_restrained_S_all 1.054 _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 0.65691(10) 0.20860(10) 0.03394(8) 0.0240(3) Uani 1 1 d . . . C1 C 0.69378(15) 0.22210(14) -0.04516(12) 0.0241(4) Uani 1 1 d . . . C2 C 0.80270(16) 0.19355(15) -0.04191(12) 0.0265(5) Uani 1 1 d . . . C3 C 0.83212(17) 0.11296(15) -0.07984(13) 0.0307(5) Uani 1 1 d . . . H3 H 0.7842 0.0762 -0.1107 0.037 Uiso 1 1 calc R . . C4 C 0.93038(17) 0.08474(16) -0.07359(14) 0.0347(5) Uani 1 1 d . . . H4 H 0.9489 0.0285 -0.0988 0.042 Uiso 1 1 calc R . . C5 C 1.00098(17) 0.13931(17) -0.03041(14) 0.0352(5) Uani 1 1 d . . . H5 H 1.0683 0.1209 -0.0263 0.042 Uiso 1 1 calc R . . C6 C 0.97342(16) 0.22050(16) 0.00660(14) 0.0326(5) Uani 1 1 d . . . H6 H 1.0224 0.2583 0.0352 0.039 Uiso 1 1 calc R . . C7 C 0.87446(16) 0.24803(15) 0.00274(13) 0.0268(5) Uani 1 1 d . . . C8 C 0.84771(16) 0.33155(14) 0.05016(12) 0.0263(5) Uani 1 1 d . . . C9 C 0.90191(17) 0.41378(16) 0.04689(14) 0.0339(5) Uani 1 1 d . . . H9 H 0.9550 0.4165 0.0133 0.041 Uiso 1 1 calc R . . C10 C 0.87994(19) 0.49189(16) 0.09170(15) 0.0386(6) Uani 1 1 d . . . H10 H 0.9182 0.5472 0.0894 0.046 Uiso 1 1 calc R . . C11 C 0.80182(18) 0.48863(16) 0.13976(14) 0.0349(5) Uani 1 1 d . . . H11 H 0.7859 0.5419 0.1704 0.042 Uiso 1 1 calc R . . C12 C 0.74721(16) 0.40771(14) 0.14298(13) 0.0282(5) Uani 1 1 d . . . H12 H 0.6932 0.4064 0.1756 0.034 Uiso 1 1 calc R . . C13 C 0.76898(15) 0.32793(14) 0.09971(12) 0.0239(4) Uani 1 1 d . . . C14 C 0.71397(15) 0.23559(14) 0.10853(12) 0.0225(4) Uani 1 1 d . . . C15 C 0.62834(16) 0.15675(14) -0.10119(13) 0.0271(5) Uani 1 1 d . . . C16 C 0.6125(2) 0.17309(18) -0.18436(14) 0.0454(7) Uani 1 1 d . . . H16 H 0.6389 0.2279 -0.2067 0.055 Uiso 1 1 calc R . . C17 C 0.5589(2) 0.11103(19) -0.23518(15) 0.0544(8) Uani 1 1 d . . . H17 H 0.5488 0.1239 -0.2917 0.065 Uiso 1 1 calc R . . C18 C 0.5202(2) 0.03087(18) -0.20464(16) 0.0457(7) Uani 1 1 d . . . H18 H 0.4844 -0.0121 -0.2399 0.055 Uiso 1 1 calc R . . C19 C 0.53406(19) 0.01378(18) -0.12238(15) 0.0411(6) Uani 1 1 d . . . H19 H 0.5074 -0.0411 -0.1005 0.049 Uiso 1 1 calc R . . C20 C 0.58712(17) 0.07694(17) -0.07131(14) 0.0349(5) Uani 1 1 d . . . H20 H 0.5952 0.0649 -0.0145 0.042 Uiso 1 1 calc R . . C21 C 0.67589(16) 0.32356(15) -0.07532(12) 0.0260(5) Uani 1 1 d . . . C22 C 0.73621(17) 0.36457(16) -0.12927(14) 0.0340(5) Uani 1 1 d . . . H22 H 0.7933 0.3325 -0.1434 0.041 Uiso 1 1 calc R . . C23 C 0.71346(19) 0.45207(16) -0.16260(15) 0.0391(6) Uani 1 1 d . . . H23 H 0.7554 0.4796 -0.1989 0.047 Uiso 1 1 calc R . . C24 C 0.63027(19) 0.49907(16) -0.14330(15) 0.0388(6) Uani 1 1 d . . . H24 H 0.6144 0.5586 -0.1666 0.047 Uiso 1 1 calc R . . C25 C 0.57001(19) 0.45886(16) -0.08972(14) 0.0375(6) Uani 1 1 d . . . H25 H 0.5128 0.4911 -0.0760 0.045 Uiso 1 1 calc R . . C26 C 0.59268(16) 0.37188(15) -0.05608(13) 0.0304(5) Uani 1 1 d . . . H26 H 0.5508 0.3450 -0.0194 0.037 Uiso 1 1 calc R . . C27 C 0.78672(15) 0.15712(14) 0.13909(11) 0.0229(4) Uani 1 1 d . . . C28 C 0.87391(15) 0.17762(16) 0.18669(13) 0.0290(5) Uani 1 1 d . . . H28 H 0.8927 0.2410 0.1958 0.035 Uiso 1 1 calc R . . C29 C 0.93367(16) 0.10655(17) 0.22094(13) 0.0331(5) Uani 1 1 d . . . H29 H 0.9929 0.1216 0.2531 0.040 Uiso 1 1 calc R . . C30 C 0.90724(18) 0.01427(17) 0.20833(14) 0.0348(5) Uani 1 1 d . . . H30 H 0.9481 -0.0344 0.2316 0.042 Uiso 1 1 calc R . . C31 C 0.82073(18) -0.00698(16) 0.16158(14) 0.0354(5) Uani 1 1 d . . . H31 H 0.8022 -0.0705 0.1526 0.042 Uiso 1 1 calc R . . C32 C 0.76102(16) 0.06397(15) 0.12779(13) 0.0288(5) Uani 1 1 d . . . H32 H 0.7014 0.0485 0.0963 0.035 Uiso 1 1 calc R . . C33 C 0.63617(15) 0.24077(13) 0.17082(12) 0.0225(4) Uani 1 1 d . . . C34 C 0.66663(16) 0.24037(14) 0.25389(13) 0.0266(5) Uani 1 1 d . . . H34 H 0.7351 0.2389 0.2712 0.032 Uiso 1 1 calc R . . C35 C 0.59872(16) 0.24214(15) 0.31126(13) 0.0286(5) Uani 1 1 d . . . H35 H 0.6208 0.2421 0.3675 0.034 Uiso 1 1 calc R . . C36 C 0.49829(16) 0.24399(15) 0.28706(14) 0.0313(5) Uani 1 1 d . . . H36 H 0.4515 0.2447 0.3263 0.038 Uiso 1 1 calc R . . C37 C 0.46762(17) 0.24482(16) 0.20517(14) 0.0334(5) Uani 1 1 d . . . H37 H 0.3991 0.2464 0.1880 0.040 Uiso 1 1 calc R . . C38 C 0.53600(15) 0.24330(15) 0.14735(13) 0.0276(5) Uani 1 1 d . . . H38 H 0.5137 0.2440 0.0912 0.033 Uiso 1 1 calc R . . C39 C 0.2513(2) 0.2037(2) 0.06181(16) 0.0456(6) Uani 1 1 d . . . C40 C 0.2950(2) 0.1496(2) 0.00772(19) 0.0596(8) Uani 1 1 d . . . H40 H 0.2937 0.0835 0.0133 0.071 Uiso 1 1 calc R . . C41 C 0.3409(2) 0.1885(3) -0.0549(2) 0.0777(12) Uani 1 1 d . . . H41 H 0.3715 0.1496 -0.0919 0.093 Uiso 1 1 calc R . . C42 C 0.3426(3) 0.2845(4) -0.0639(2) 0.0843(14) Uani 1 1 d . . . H42 H 0.3741 0.3126 -0.1068 0.101 Uiso 1 1 calc R . . C43 C 0.2972(3) 0.3388(2) -0.0088(2) 0.0705(11) Uani 1 1 d . . . H43 H 0.2972 0.4050 -0.0139 0.085 Uiso 1 1 calc R . . C44 C 0.2526(2) 0.2983(2) 0.05247(18) 0.0525(7) Uani 1 1 d . . . H44 H 0.2216 0.3367 0.0896 0.063 Uiso 1 1 calc R . . C45 C 0.2042(3) 0.1597(3) 0.1316(2) 0.0833(12) Uani 1 1 d . . . H45A H 0.1499 0.1190 0.1104 0.125 Uiso 1 1 calc R . . H45B H 0.1787 0.2088 0.1654 0.125 Uiso 1 1 calc R . . H45C H 0.2534 0.1225 0.1644 0.125 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 0.0256(7) 0.0305(8) 0.0164(7) -0.0017(6) 0.0043(5) -0.0012(6) C1 0.0280(11) 0.0292(11) 0.0163(10) -0.0003(8) 0.0074(8) 0.0028(9) C2 0.0323(11) 0.0283(11) 0.0202(10) 0.0046(8) 0.0092(8) 0.0035(9) C3 0.0376(12) 0.0283(11) 0.0278(11) 0.0018(9) 0.0109(9) 0.0015(10) C4 0.0402(13) 0.0325(12) 0.0341(13) 0.0045(10) 0.0182(10) 0.0077(10) C5 0.0299(12) 0.0444(14) 0.0336(12) 0.0107(11) 0.0145(9) 0.0067(10) C6 0.0299(12) 0.0414(13) 0.0278(11) 0.0055(10) 0.0094(9) 0.0005(10) C7 0.0291(11) 0.0313(11) 0.0212(10) 0.0057(8) 0.0089(8) 0.0015(9) C8 0.0300(11) 0.0289(11) 0.0202(10) 0.0014(8) 0.0034(8) -0.0004(9) C9 0.0365(12) 0.0369(12) 0.0293(12) 0.0027(10) 0.0088(9) -0.0067(10) C10 0.0500(15) 0.0302(12) 0.0361(13) 0.0009(10) 0.0069(11) -0.0111(11) C11 0.0486(14) 0.0271(11) 0.0294(12) -0.0018(9) 0.0063(10) -0.0022(10) C12 0.0336(11) 0.0267(11) 0.0248(11) 0.0005(9) 0.0056(9) 0.0010(9) C13 0.0261(10) 0.0242(10) 0.0211(10) 0.0032(8) 0.0003(8) 0.0009(8) C14 0.0243(10) 0.0257(10) 0.0174(10) -0.0020(8) 0.0021(8) -0.0002(8) C15 0.0310(11) 0.0269(11) 0.0237(10) -0.0017(9) 0.0037(8) 0.0063(9) C16 0.0720(19) 0.0367(13) 0.0263(12) 0.0011(10) -0.0034(12) -0.0054(13) C17 0.089(2) 0.0467(15) 0.0244(13) -0.0052(11) -0.0121(14) -0.0001(15) C18 0.0541(16) 0.0403(14) 0.0400(14) -0.0127(11) -0.0102(12) 0.0005(12) C19 0.0470(15) 0.0387(13) 0.0373(14) -0.0050(11) 0.0033(11) -0.0095(11) C20 0.0406(13) 0.0403(13) 0.0240(12) -0.0013(10) 0.0038(10) -0.0040(11) C21 0.0308(11) 0.0278(11) 0.0191(10) -0.0022(8) 0.0007(8) 0.0008(9) C22 0.0379(13) 0.0340(12) 0.0311(12) 0.0049(10) 0.0093(10) 0.0016(10) C23 0.0490(15) 0.0336(13) 0.0344(13) 0.0077(10) 0.0028(11) -0.0072(11) C24 0.0529(15) 0.0274(12) 0.0340(13) 0.0028(10) -0.0078(11) 0.0018(11) C25 0.0455(14) 0.0335(12) 0.0331(12) -0.0050(10) 0.0002(10) 0.0092(11) C26 0.0351(12) 0.0333(12) 0.0230(11) -0.0011(9) 0.0034(9) 0.0033(10) C27 0.0257(10) 0.0282(11) 0.0161(10) 0.0021(8) 0.0087(8) 0.0019(8) C28 0.0285(11) 0.0320(11) 0.0273(11) 0.0051(9) 0.0066(9) -0.0003(9) C29 0.0278(11) 0.0448(13) 0.0271(11) 0.0073(10) 0.0045(9) 0.0044(10) C30 0.0385(13) 0.0383(13) 0.0290(12) 0.0081(10) 0.0107(10) 0.0127(10) C31 0.0461(14) 0.0273(11) 0.0334(13) 0.0019(10) 0.0071(10) 0.0046(10) C32 0.0332(12) 0.0273(11) 0.0261(11) 0.0003(9) 0.0036(9) 0.0005(9) C33 0.0259(10) 0.0191(9) 0.0230(10) -0.0002(8) 0.0059(8) 0.0006(8) C34 0.0256(11) 0.0307(11) 0.0239(11) -0.0017(9) 0.0049(8) 0.0017(9) C35 0.0354(12) 0.0306(11) 0.0208(10) -0.0015(9) 0.0075(9) 0.0014(9) C36 0.0316(12) 0.0340(12) 0.0305(12) -0.0035(9) 0.0142(9) -0.0045(9) C37 0.0258(11) 0.0408(13) 0.0343(13) -0.0058(10) 0.0061(9) -0.0026(10) C38 0.0267(11) 0.0314(11) 0.0249(11) -0.0013(9) 0.0035(9) 0.0003(9) C39 0.0449(15) 0.0532(16) 0.0364(14) 0.0008(12) -0.0084(11) -0.0076(13) C40 0.068(2) 0.0468(16) 0.0596(19) -0.0099(14) -0.0154(17) 0.0139(15) C41 0.0439(18) 0.125(3) 0.063(2) -0.038(2) -0.0008(16) 0.016(2) C42 0.056(2) 0.158(4) 0.0358(17) 0.017(2) -0.0154(15) -0.053(3) C43 0.086(2) 0.0565(19) 0.061(2) 0.0161(16) -0.0378(19) -0.0250(18) C44 0.0538(17) 0.0477(16) 0.0531(17) -0.0132(14) -0.0116(14) 0.0040(13) C45 0.088(3) 0.109(3) 0.051(2) 0.009(2) -0.0059(18) -0.040(2) _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 C14 1.448(2) . ? O1 C1 1.454(2) . ? C1 C2 1.535(3) . ? C1 C15 1.541(3) . ? C1 C21 1.546(3) . ? C2 C3 1.388(3) . ? C2 C7 1.405(3) . ? C3 C4 1.392(3) . ? C4 C5 1.385(3) . ? C5 C6 1.379(3) . ? C6 C7 1.400(3) . ? C7 C8 1.491(3) . ? C8 C9 1.392(3) . ? C8 C13 1.407(3) . ? C9 C10 1.387(3) . ? C10 C11 1.384(3) . ? C11 C12 1.379(3) . ? C12 C13 1.392(3) . ? C13 C14 1.531(3) . ? C14 C33 1.544(3) . ? C14 C27 1.551(3) . ? C15 C20 1.382(3) . ? C15 C16 1.391(3) . ? C16 C17 1.383(3) . ? C17 C18 1.376(4) . ? C18 C19 1.377(4) . ? C19 C20 1.392(3) . ? C21 C26 1.388(3) . ? C21 C22 1.395(3) . ? C22 C23 1.390(3) . ? C23 C24 1.379(4) . ? C24 C25 1.385(4) . ? C25 C26 1.385(3) . ? C27 C32 1.385(3) . ? C27 C28 1.395(3) . ? C28 C29 1.390(3) . ? C29 C30 1.378(3) . ? C30 C31 1.383(3) . ? C31 C32 1.385(3) . ? C33 C38 1.384(3) . ? C33 C34 1.397(3) . ? C34 C35 1.383(3) . ? C35 C36 1.390(3) . ? C36 C37 1.379(3) . ? C37 C38 1.393(3) . ? C39 C40 1.359(4) . ? C39 C44 1.361(4) . ? C39 C45 1.506(4) . ? C40 C41 1.375(5) . ? C41 C42 1.380(6) . ? C42 C43 1.384(6) . ? C43 C44 1.356(5) . ? 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 C14 O1 C1 121.80(15) . . ? O1 C1 C2 110.13(16) . . ? O1 C1 C15 103.38(16) . . ? C2 C1 C15 111.37(17) . . ? O1 C1 C21 110.92(16) . . ? C2 C1 C21 112.61(17) . . ? C15 C1 C21 108.03(16) . . ? C3 C2 C7 118.8(2) . . ? C3 C2 C1 121.5(2) . . ? C7 C2 C1 119.67(19) . . ? C2 C3 C4 121.4(2) . . ? C5 C4 C3 119.5(2) . . ? C6 C5 C4 119.9(2) . . ? C5 C6 C7 121.0(2) . . ? C6 C7 C2 119.3(2) . . ? C6 C7 C8 118.7(2) . . ? C2 C7 C8 121.89(19) . . ? C9 C8 C13 119.22(19) . . ? C9 C8 C7 120.03(19) . . ? C13 C8 C7 120.74(18) . . ? C10 C9 C8 121.2(2) . . ? C11 C10 C9 119.5(2) . . ? C12 C11 C10 119.7(2) . . ? C11 C12 C13 121.8(2) . . ? C12 C13 C8 118.51(19) . . ? C12 C13 C14 121.92(19) . . ? C8 C13 C14 119.47(18) . . ? O1 C14 C13 112.22(16) . . ? O1 C14 C33 103.43(15) . . ? C13 C14 C33 113.15(16) . . ? O1 C14 C27 111.23(15) . . ? C13 C14 C27 110.55(16) . . ? C33 C14 C27 105.92(15) . . ? C20 C15 C16 117.4(2) . . ? C20 C15 C1 121.16(19) . . ? C16 C15 C1 121.4(2) . . ? C17 C16 C15 121.2(2) . . ? C18 C17 C16 120.7(2) . . ? C17 C18 C19 119.1(2) . . ? C18 C19 C20 120.0(2) . . ? C15 C20 C19 121.6(2) . . ? C26 C21 C22 118.5(2) . . ? C26 C21 C1 120.08(19) . . ? C22 C21 C1 121.05(19) . . ? C23 C22 C21 120.5(2) . . ? C24 C23 C22 120.3(2) . . ? C23 C24 C25 119.5(2) . . ? C24 C25 C26 120.4(2) . . ? C25 C26 C21 120.8(2) . . ? C32 C27 C28 118.02(19) . . ? C32 C27 C14 120.36(18) . . ? C28 C27 C14 121.19(18) . . ? C29 C28 C27 120.9(2) . . ? C30 C29 C28 120.2(2) . . ? C29 C30 C31 119.5(2) . . ? C30 C31 C32 120.2(2) . . ? C27 C32 C31 121.2(2) . . ? C38 C33 C34 118.21(19) . . ? C38 C33 C14 122.18(18) . . ? C34 C33 C14 119.59(18) . . ? C35 C34 C33 121.03(19) . . ? C34 C35 C36 120.3(2) . . ? C37 C36 C35 119.0(2) . . ? C36 C37 C38 120.7(2) . . ? C33 C38 C37 120.7(2) . . ? C40 C39 C44 118.7(3) . . ? C40 C39 C45 120.4(3) . . ? C44 C39 C45 120.9(3) . . ? C39 C40 C41 121.4(3) . . ? C40 C41 C42 119.7(3) . . ? C41 C42 C43 118.4(3) . . ? C44 C43 C42 120.5(3) . . ? C43 C44 C39 121.4(3) . . ? _diffrn_measured_fraction_theta_max 0.963 _diffrn_reflns_theta_full 67.53 _diffrn_measured_fraction_theta_full 0.963 _refine_diff_density_max 0.327 _refine_diff_density_min -0.283 _refine_diff_density_rms 0.047 data_hm7 _database_code_CSD 190258 _audit_creation_method SHELXL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C42 H36 O5' _chemical_formula_weight 620.71 _chemical_melting_point ? _chemical_compound_source ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0181 0.0091 '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' 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M I2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z' 'x+1/2, y+1/2, z+1/2' '-x+1/2, y+1/2, -z+1/2' _cell_length_a 9.656(3) _cell_length_b 9.089(3) _cell_length_c 18.142(6) _cell_angle_alpha 90.00 _cell_angle_beta 91.24(2) _cell_angle_gamma 90.00 _cell_volume 1591.8(9) _cell_formula_units_Z 2 _cell_measurement_temperature 160(2) _cell_measurement_reflns_used 34 _cell_measurement_theta_min 21.18 _cell_measurement_theta_max 24.95 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.33 _exptl_crystal_size_min 0.23 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.295 _exptl_crystal_density_method ? _exptl_crystal_F_000 656 _exptl_absorpt_coefficient_mu 0.668 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 160(2) _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'Stoe-Siemens diffractometer' _diffrn_measurement_method '\w/\q scans with on-line profile fitting' _diffrn_standards_number 5 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 60 _diffrn_standards_decay_% 0 _diffrn_reflns_number 5382 _diffrn_reflns_av_R_equivalents 0.0250 _diffrn_reflns_av_sigmaI/netI 0.0339 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 4.88 _diffrn_reflns_theta_max 65.01 _reflns_number_total 2680 _reflns_number_observed 2646 _reflns_observed_criterion >2sigma(I) _computing_data_collection 'Stoe DIF4' _computing_cell_refinement 'Stoe DIF4' _computing_data_reduction 'local programs' _computing_structure_solution 'Siemens SHELXTL' _computing_structure_refinement 'Siemens SHELXTL' _computing_molecular_graphics 'Siemens SHELXTL' _computing_publication_material 'SHELXTL and local programs' _refine_special_details ; Refinement of F^2^ against ALL reflections. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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 w=1/[\s^2^(Fo^2^)+(0.0270P)^2^+0.4877P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary 'all non-H atoms found by direct methods' _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment ? _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0046(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 0.06(15) _refine_ls_number_reflns 2680 _refine_ls_number_parameters 216 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0249 _refine_ls_R_factor_obs 0.0245 _refine_ls_wR_factor_all 0.0646 _refine_ls_wR_factor_obs 0.0642 _refine_ls_goodness_of_fit_all 1.027 _refine_ls_goodness_of_fit_obs 1.027 _refine_ls_restrained_S_all 1.027 _refine_ls_restrained_S_obs 1.027 _refine_ls_shift/esd_max 0.000 _refine_ls_shift/esd_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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group C1 C -0.12618(12) 0.17963(13) 0.01663(7) 0.0211(3) Uani 1 d . . O1 O 0.0000 0.10050(13) 0.0000 0.0208(3) Uani 1 d S . C2 C -0.09421(12) 0.31031(14) 0.06781(7) 0.0243(3) Uani 1 d . . C3 C -0.12784(14) 0.30975(17) 0.14230(8) 0.0318(3) Uani 1 d . . H3 H -0.1751 0.2277 0.1622 0.038 Uiso 1 calc R . C4 C -0.09284(16) 0.4280(2) 0.18755(9) 0.0443(4) Uani 1 d . . H4 H -0.1149 0.4256 0.2383 0.053 Uiso 1 calc R . C5 C -0.02618(16) 0.54873(19) 0.15899(10) 0.0471(5) Uani 1 d . . H5 H -0.0040 0.6303 0.1898 0.057 Uiso 1 calc R . C6 C 0.00846(14) 0.55098(16) 0.08513(10) 0.0393(4) Uani 1 d . . H6 H 0.0542 0.6345 0.0657 0.047 Uiso 1 calc R . C7 C -0.02313(13) 0.43205(15) 0.03897(8) 0.0283(3) Uani 1 d . . C8 C -0.20297(12) 0.23001(13) -0.05478(7) 0.0204(3) Uani 1 d . . C9 C -0.18810(12) 0.15282(14) -0.12076(7) 0.0223(3) Uani 1 d . . H9 H -0.1261 0.0718 -0.1225 0.027 Uiso 1 calc R . C10 C -0.26265(13) 0.19295(15) -0.18361(7) 0.0250(3) Uani 1 d . . H10 H -0.2509 0.1400 -0.2282 0.030 Uiso 1 calc R . C11 C -0.35498(12) 0.31081(14) -0.18180(7) 0.0233(3) Uani 1 d . . C12 C -0.37407(12) 0.38575(14) -0.11627(7) 0.0232(3) Uani 1 d . . H12 H -0.4389 0.4642 -0.1141 0.028 Uiso 1 calc R . C13 C -0.29743(12) 0.34501(14) -0.05369(7) 0.0224(3) Uani 1 d . . H13 H -0.3101 0.3974 -0.0090 0.027 Uiso 1 calc R . O2 O -0.42174(10) 0.34448(11) -0.24744(5) 0.0321(2) Uani 1 d . . C14 C -0.53486(16) 0.44456(18) -0.24444(8) 0.0366(3) Uani 1 d . . H14A H -0.5992 0.4122 -0.2067 0.055 Uiso 1 calc R . H14B H -0.5831 0.4474 -0.2925 0.055 Uiso 1 calc R . H14C H -0.5001 0.5430 -0.2321 0.055 Uiso 1 calc R . C15 C -0.22144(12) 0.06360(14) 0.05097(6) 0.0208(3) Uani 1 d . . C16 C -0.35449(14) 0.10297(15) 0.07113(8) 0.0273(3) Uani 1 d . . H16 H -0.3808 0.2036 0.0684 0.033 Uiso 1 calc R . C17 C -0.45019(13) 0.00106(15) 0.09508(7) 0.0278(3) Uani 1 d . . H17 H -0.5400 0.0318 0.1090 0.033 Uiso 1 calc R . C18 C -0.41354(13) -0.14640(15) 0.09856(7) 0.0254(3) Uani 1 d . . C19 C -0.28018(13) -0.18806(15) 0.08085(8) 0.0278(3) Uani 1 d . . H19 H -0.2537 -0.2885 0.0847 0.033 Uiso 1 calc R . C20 C -0.18491(13) -0.08432(14) 0.05751(7) 0.0244(3) Uani 1 d . . H20 H -0.0938 -0.1146 0.0459 0.029 Uiso 1 calc R . O3 O -0.50258(10) -0.25643(11) 0.11877(6) 0.0348(3) Uani 1 d . . C21 C -0.64296(14) -0.21422(17) 0.13131(9) 0.0353(3) Uani 1 d . . H21A H -0.6458 -0.1476 0.1737 0.053 Uiso 1 calc R . H21B H -0.6983 -0.3021 0.1413 0.053 Uiso 1 calc R . H21C H -0.6808 -0.1641 0.0875 0.053 Uiso 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 C1 0.0173(6) 0.0205(6) 0.0256(7) -0.0024(5) 0.0005(5) 0.0021(5) O1 0.0150(5) 0.0178(6) 0.0296(7) 0.000 0.0016(5) 0.000 C2 0.0195(6) 0.0224(7) 0.0305(7) -0.0041(5) -0.0073(5) 0.0063(5) C3 0.0257(6) 0.0376(8) 0.0319(8) -0.0095(6) -0.0060(5) 0.0111(6) C4 0.0332(8) 0.0569(11) 0.0422(8) -0.0248(9) -0.0120(7) 0.0157(8) C5 0.0316(8) 0.0401(9) 0.0688(12) -0.0321(9) -0.0171(8) 0.0106(7) C6 0.0246(6) 0.0231(7) 0.0695(11) -0.0158(7) -0.0121(7) 0.0059(6) C7 0.0190(6) 0.0198(6) 0.0457(8) -0.0042(6) -0.0102(5) 0.0064(5) C8 0.0171(6) 0.0195(6) 0.0247(7) 0.0010(5) 0.0007(5) -0.0046(5) C9 0.0187(6) 0.0204(6) 0.0278(7) -0.0014(5) 0.0024(5) -0.0018(5) C10 0.0250(6) 0.0257(6) 0.0244(7) -0.0037(5) 0.0022(5) -0.0044(5) C11 0.0203(6) 0.0254(7) 0.0242(7) 0.0025(5) -0.0024(5) -0.0056(5) C12 0.0193(6) 0.0201(6) 0.0300(7) 0.0017(5) -0.0018(5) -0.0013(5) C13 0.0203(6) 0.0218(7) 0.0251(6) -0.0033(5) 0.0009(5) -0.0012(5) O2 0.0342(5) 0.0348(5) 0.0268(5) 0.0008(4) -0.0079(4) 0.0035(4) C14 0.0313(7) 0.0446(9) 0.0335(8) 0.0040(7) -0.0084(6) 0.0047(6) C15 0.0212(6) 0.0228(6) 0.0185(6) 0.0000(5) -0.0004(5) 0.0017(5) C16 0.0262(6) 0.0224(6) 0.0336(7) 0.0014(5) 0.0051(5) 0.0051(5) C17 0.0221(6) 0.0300(7) 0.0315(7) 0.0044(6) 0.0069(5) 0.0038(6) C18 0.0252(6) 0.0257(7) 0.0254(7) 0.0056(5) 0.0016(5) -0.0011(5) C19 0.0263(6) 0.0216(6) 0.0356(8) 0.0061(6) 0.0037(6) 0.0040(5) C20 0.0201(6) 0.0245(7) 0.0285(7) 0.0001(6) 0.0020(5) 0.0035(5) O3 0.0261(5) 0.0281(5) 0.0505(6) 0.0100(5) 0.0104(4) -0.0004(4) C21 0.0245(7) 0.0346(8) 0.0470(9) 0.0093(7) 0.0082(6) -0.0002(6) _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 C1 O1 1.4521(13) . ? C1 C2 1.5349(17) . ? C1 C15 1.5399(18) . ? C1 C8 1.5480(17) . ? O1 C1 1.4521(13) 2 ? C2 C3 1.397(2) . ? C2 C7 1.4088(19) . ? C3 C4 1.390(2) . ? C4 C5 1.379(3) . ? C5 C6 1.388(3) . ? C6 C7 1.397(2) . ? C7 C7 1.492(3) 2 ? C8 C13 1.3877(18) . ? C8 C9 1.3975(18) . ? C9 C10 1.3842(19) . ? C10 C11 1.3945(19) . ? C11 O2 1.3763(16) . ? C11 C12 1.3859(19) . ? C12 C13 1.3919(18) . ? O2 C14 1.4233(18) . ? C15 C16 1.3902(18) . ? C15 C20 1.3943(19) . ? C16 C17 1.3849(19) . ? C17 C18 1.387(2) . ? C18 O3 1.3738(16) . ? C18 C19 1.3866(19) . ? C19 C20 1.3897(18) . ? O3 C21 1.4317(17) . ? 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 110.51(9) . . ? O1 C1 C15 104.84(10) . . ? C2 C1 C15 113.54(10) . . ? O1 C1 C8 111.19(9) . . ? C2 C1 C8 111.33(10) . . ? C15 C1 C8 105.17(9) . . ? C1 O1 C1 120.62(13) 2 . ? C3 C2 C7 119.18(12) . . ? C3 C2 C1 122.32(12) . . ? C7 C2 C1 118.44(12) . . ? C4 C3 C2 120.67(15) . . ? C5 C4 C3 120.19(15) . . ? C4 C5 C6 119.91(14) . . ? C5 C6 C7 120.87(16) . . ? C6 C7 C2 119.13(14) . . ? C6 C7 C7 120.14(12) . 2 ? C2 C7 C7 120.68(9) . 2 ? C13 C8 C9 118.04(11) . . ? C13 C8 C1 120.93(11) . . ? C9 C8 C1 120.80(11) . . ? C10 C9 C8 120.80(12) . . ? C9 C10 C11 120.29(12) . . ? O2 C11 C12 124.36(11) . . ? O2 C11 C10 115.99(11) . . ? C12 C11 C10 119.65(11) . . ? C11 C12 C13 119.39(12) . . ? C8 C13 C12 121.79(12) . . ? C11 O2 C14 117.03(11) . . ? C16 C15 C20 117.34(12) . . ? C16 C15 C1 119.58(11) . . ? C20 C15 C1 122.86(11) . . ? C17 C16 C15 122.49(13) . . ? C16 C17 C18 119.28(12) . . ? O3 C18 C19 116.92(12) . . ? O3 C18 C17 123.70(12) . . ? C19 C18 C17 119.37(12) . . ? C18 C19 C20 120.63(12) . . ? C19 C20 C15 120.81(12) . . ? C18 O3 C21 116.59(11) . . ? _refine_diff_density_max 0.130 _refine_diff_density_min -0.119 _refine_diff_density_rms 0.025 data_hm15 _database_code_CSD 190259 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C42 H37 N O4' _chemical_formula_weight 619.73 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0181 0.0091 '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' 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M I2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z' 'x+1/2, y+1/2, z+1/2' '-x+1/2, y+1/2, -z+1/2' _cell_length_a 9.8515(11) _cell_length_b 8.9880(10) _cell_length_c 17.9926(19) _cell_angle_alpha 90.00 _cell_angle_beta 91.406(4) _cell_angle_gamma 90.00 _cell_volume 1592.7(3) _cell_formula_units_Z 2 _cell_measurement_temperature 160(2) _cell_measurement_reflns_used 3769 _cell_measurement_theta_min 2.0 _cell_measurement_theta_max 27.5 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.56 _exptl_crystal_size_mid 0.50 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.292 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 656 _exptl_absorpt_coefficient_mu 0.652 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.534 _exptl_absorpt_correction_T_max 0.918 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 160(2) _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Stoe-Siemens diffractometer' _diffrn_measurement_method '\w/\q scans with on-line profile fitting' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 5 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 60 _diffrn_standards_decay_% 2 _diffrn_reflns_number 3900 _diffrn_reflns_av_R_equivalents 0.0228 _diffrn_reflns_av_sigmaI/netI 0.0190 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 4.92 _diffrn_reflns_theta_max 67.61 _reflns_number_total 2785 _reflns_number_gt 2769 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Stoe DIF4' _computing_cell_refinement 'local programs' _computing_data_reduction 'local programs' _computing_structure_solution 'Siemens SHELXTL' _computing_structure_refinement 'Siemens SHELXTL' _computing_molecular_graphics 'Siemens SHELXTL' _computing_publication_material 'SHELXTL and local programs' _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^)+(0.0736P)^2^+0.5813P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary 'all non-H atoms found by direct methods' _atom_sites_solution_hydrogens 'geom except H1 coords freely refined' _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0037(4) _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 0.2(2) _refine_ls_number_reflns 2785 _refine_ls_number_parameters 220 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0390 _refine_ls_R_factor_gt 0.0388 _refine_ls_wR_factor_ref 0.1051 _refine_ls_wR_factor_gt 0.1050 _refine_ls_goodness_of_fit_ref 1.067 _refine_ls_restrained_S_all 1.067 _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 N1 N 0.5000 0.7875(2) 0.5000 0.0202(4) Uani 1 2 d S . . H1 H 0.514(4) 0.863(5) 0.536(2) 0.024 Uiso 0.50 1 d P . . C1 C 0.37307(15) 0.70682(19) 0.51591(9) 0.0212(4) Uani 1 1 d . . . C2 C 0.40478(16) 0.57431(19) 0.56745(9) 0.0230(4) Uani 1 1 d . . . C3 C 0.47651(17) 0.4528(2) 0.53904(10) 0.0275(4) Uani 1 1 d . . . C4 C 0.50768(19) 0.3327(2) 0.58521(13) 0.0380(5) Uani 1 1 d . . . H4 H 0.5542 0.2494 0.5656 0.046 Uiso 1 1 calc R . . C5 C 0.4719(2) 0.3326(3) 0.65938(13) 0.0454(6) Uani 1 1 d . . . H5 H 0.4937 0.2498 0.6903 0.055 Uiso 1 1 calc R . . C6 C 0.4045(2) 0.4538(3) 0.68786(12) 0.0419(5) Uani 1 1 d . . . H6 H 0.3813 0.4553 0.7388 0.050 Uiso 1 1 calc R . . C7 C 0.37041(18) 0.5733(2) 0.64238(10) 0.0315(4) Uani 1 1 d . . . H7 H 0.3231 0.6556 0.6624 0.038 Uiso 1 1 calc R . . C8 C 0.27479(16) 0.82135(19) 0.55007(8) 0.0205(4) Uani 1 1 d . . . C9 C 0.30467(17) 0.9720(2) 0.55666(10) 0.0270(4) Uani 1 1 d . . . H9 H 0.3926 1.0063 0.5445 0.032 Uiso 1 1 calc R . . C10 C 0.20911(19) 1.0734(2) 0.58057(11) 0.0317(4) Uani 1 1 d . . . H10 H 0.2325 1.1757 0.5846 0.038 Uiso 1 1 calc R . . C11 C 0.07965(17) 1.0271(2) 0.59870(9) 0.0259(4) Uani 1 1 d . . . C12 C 0.04937(18) 0.8762(2) 0.59504(10) 0.0282(4) Uani 1 1 d . . . H12 H -0.0373 0.8414 0.6092 0.034 Uiso 1 1 calc R . . C13 C 0.14559(18) 0.7770(2) 0.57068(11) 0.0297(4) Uani 1 1 d . . . H13 H 0.1228 0.6744 0.5679 0.036 Uiso 1 1 calc R . . O1 O -0.01002(13) 1.13481(16) 0.61883(8) 0.0352(3) Uani 1 1 d . . . C14 C -0.14557(18) 1.0877(2) 0.63236(12) 0.0352(5) Uani 1 1 d . . . H14A H -0.1812 1.0326 0.5891 0.053 Uiso 1 1 calc R . . H14B H -0.2028 1.1749 0.6410 0.053 Uiso 1 1 calc R . . H14C H -0.1458 1.0232 0.6763 0.053 Uiso 1 1 calc R . . C15 C 0.29696(16) 0.65196(19) 0.44412(9) 0.0204(4) Uani 1 1 d . . . C16 C 0.30937(16) 0.7275(2) 0.37691(9) 0.0232(4) Uani 1 1 d . . . H16 H 0.3701 0.8093 0.3741 0.028 Uiso 1 1 calc R . . C17 C 0.23481(18) 0.6852(2) 0.31432(9) 0.0261(4) Uani 1 1 d . . . H17 H 0.2453 0.7375 0.2690 0.031 Uiso 1 1 calc R . . C18 C 0.14451(16) 0.5664(2) 0.31731(9) 0.0252(4) Uani 1 1 d . . . C19 C 0.12857(17) 0.49155(19) 0.38403(9) 0.0237(4) Uani 1 1 d . . . H19 H 0.0660 0.4115 0.3872 0.028 Uiso 1 1 calc R . . C20 C 0.20538(16) 0.5354(2) 0.44620(9) 0.0221(4) Uani 1 1 d . . . H20 H 0.1946 0.4834 0.4916 0.027 Uiso 1 1 calc R . . O2 O 0.07717(13) 0.53017(16) 0.25209(7) 0.0329(3) Uani 1 1 d . . . C21 C -0.0359(2) 0.4324(3) 0.25697(11) 0.0397(5) Uani 1 1 d . . . H21A H -0.0039 0.3324 0.2702 0.060 Uiso 1 1 calc R . . H21B H -0.0848 0.4290 0.2089 0.060 Uiso 1 1 calc R . . H21C H -0.0969 0.4686 0.2952 0.060 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 N1 0.0144(9) 0.0199(10) 0.0260(9) 0.000 -0.0033(7) 0.000 C1 0.0156(7) 0.0223(8) 0.0256(8) 0.0005(7) -0.0037(6) -0.0014(7) C2 0.0162(7) 0.0237(9) 0.0287(8) 0.0031(7) -0.0100(6) -0.0068(6) C3 0.0171(8) 0.0224(9) 0.0424(10) 0.0044(8) -0.0124(7) -0.0067(6) C4 0.0216(9) 0.0254(10) 0.0662(13) 0.0149(10) -0.0132(9) -0.0055(7) C5 0.0292(10) 0.0433(12) 0.0629(14) 0.0297(11) -0.0160(9) -0.0100(9) C6 0.0300(10) 0.0555(14) 0.0397(10) 0.0199(10) -0.0126(8) -0.0157(10) C7 0.0233(8) 0.0396(11) 0.0312(9) 0.0066(8) -0.0089(7) -0.0100(8) C8 0.0162(7) 0.0256(9) 0.0196(7) 0.0003(6) -0.0030(6) -0.0009(7) C9 0.0201(8) 0.0259(10) 0.0352(9) -0.0032(7) 0.0037(7) -0.0040(7) C10 0.0256(9) 0.0236(9) 0.0462(10) -0.0082(8) 0.0057(8) -0.0047(7) C11 0.0238(8) 0.0284(9) 0.0254(8) -0.0057(7) 0.0004(6) 0.0016(7) C12 0.0213(8) 0.0296(10) 0.0340(9) -0.0039(7) 0.0058(7) -0.0035(7) C13 0.0242(9) 0.0232(9) 0.0418(10) -0.0013(8) 0.0048(7) -0.0043(7) O1 0.0238(7) 0.0318(7) 0.0505(8) -0.0106(6) 0.0087(6) -0.0003(5) C14 0.0224(9) 0.0359(11) 0.0475(11) -0.0098(9) 0.0068(8) -0.0003(8) C15 0.0153(7) 0.0218(8) 0.0240(8) 0.0008(6) -0.0025(6) 0.0055(6) C16 0.0170(7) 0.0242(9) 0.0284(8) 0.0029(7) 0.0015(6) 0.0022(7) C17 0.0239(8) 0.0306(9) 0.0239(8) 0.0050(7) 0.0007(6) 0.0067(7) C18 0.0206(8) 0.0302(10) 0.0247(8) -0.0025(7) -0.0037(6) 0.0076(7) C19 0.0184(8) 0.0249(9) 0.0275(8) -0.0004(7) -0.0039(6) 0.0011(6) C20 0.0186(7) 0.0240(9) 0.0237(8) 0.0040(7) -0.0023(6) 0.0024(7) O2 0.0319(7) 0.0404(8) 0.0260(6) -0.0002(6) -0.0104(5) -0.0014(6) C21 0.0340(10) 0.0514(14) 0.0332(10) -0.0022(9) -0.0125(8) -0.0030(9) _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 N1 C1 1.4797(18) . ? N1 C1 1.4797(18) 2_656 ? C1 C2 1.537(2) . ? C1 C8 1.551(2) . ? C1 C15 1.558(2) . ? C2 C7 1.398(2) . ? C2 C3 1.404(2) . ? C3 C4 1.392(3) . ? C3 C3 1.490(4) 2_656 ? C4 C5 1.389(3) . ? C5 C6 1.381(4) . ? C6 C7 1.387(3) . ? C8 C9 1.390(3) . ? C8 C13 1.393(2) . ? C9 C10 1.386(3) . ? C10 C11 1.388(2) . ? C11 O1 1.366(2) . ? C11 C12 1.390(3) . ? C12 C13 1.380(3) . ? O1 C14 1.428(2) . ? C15 C20 1.384(2) . ? C15 C16 1.395(2) . ? C16 C17 1.383(3) . ? C17 C18 1.392(3) . ? C18 O2 1.373(2) . ? C18 C19 1.388(2) . ? C19 C20 1.392(2) . ? O2 C21 1.423(3) . ? 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 C1 N1 C1 121.28(19) . 2_656 ? N1 C1 C2 109.66(13) . . ? N1 C1 C8 106.87(14) . . ? C2 C1 C8 113.26(13) . . ? N1 C1 C15 112.75(11) . . ? C2 C1 C15 109.98(14) . . ? C8 C1 C15 104.26(12) . . ? C7 C2 C3 118.81(16) . . ? C7 C2 C1 122.44(16) . . ? C3 C2 C1 118.67(15) . . ? C4 C3 C2 119.46(18) . . ? C4 C3 C3 119.58(15) . 2_656 ? C2 C3 C3 120.93(12) . 2_656 ? C5 C4 C3 121.1(2) . . ? C6 C5 C4 119.44(19) . . ? C5 C6 C7 120.3(2) . . ? C6 C7 C2 120.9(2) . . ? C9 C8 C13 116.69(16) . . ? C9 C8 C1 123.19(14) . . ? C13 C8 C1 119.95(15) . . ? C10 C9 C8 121.52(16) . . ? C9 C10 C11 120.69(18) . . ? O1 C11 C10 116.97(17) . . ? O1 C11 C12 124.41(15) . . ? C10 C11 C12 118.63(16) . . ? C13 C12 C11 119.80(16) . . ? C12 C13 C8 122.61(17) . . ? C11 O1 C14 116.66(15) . . ? C20 C15 C16 117.58(15) . . ? C20 C15 C1 121.22(14) . . ? C16 C15 C1 120.95(15) . . ? C17 C16 C15 121.08(16) . . ? C16 C17 C18 120.46(15) . . ? O2 C18 C19 124.18(16) . . ? O2 C18 C17 116.41(15) . . ? C19 C18 C17 119.41(15) . . ? C18 C19 C20 119.15(15) . . ? C15 C20 C19 122.31(15) . . ? C18 O2 C21 117.13(15) . . ? _diffrn_measured_fraction_theta_max 0.986 _diffrn_reflns_theta_full 67.61 _diffrn_measured_fraction_theta_full 0.986 _refine_diff_density_max 0.207 _refine_diff_density_min -0.168 _refine_diff_density_rms 0.039 data_hm5 _database_code_CSD 190260 _audit_creation_method SHELXL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C42 H38 O6' _chemical_formula_weight 638.72 _chemical_melting_point ? _chemical_compound_source ? 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 10.162(4) _cell_length_b 12.856(5) _cell_length_c 13.729(5) _cell_angle_alpha 74.83(3) _cell_angle_beta 71.95(2) _cell_angle_gamma 85.00(2) _cell_volume 1645.9(11) _cell_formula_units_Z 2 _cell_measurement_temperature 160(2) _cell_measurement_reflns_used 49 _cell_measurement_theta_min 10.11 _cell_measurement_theta_max 12.48 _exptl_crystal_description 'thick plate' _exptl_crystal_colour colourless _exptl_crystal_size_max 0.65 _exptl_crystal_size_mid 0.33 _exptl_crystal_size_min 0.17 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.289 _exptl_crystal_density_method ? _exptl_crystal_F_000 676 _exptl_absorpt_coefficient_mu 0.085 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 160(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 'Stoe-Siemens diffractometer' _diffrn_measurement_method '\w/\q scans with on-line profile fitting' _diffrn_standards_number 5 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 60 _diffrn_standards_decay_% -1 _diffrn_reflns_number 7044 _diffrn_reflns_av_R_equivalents 0.0348 _diffrn_reflns_av_sigmaI/netI 0.0499 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.52 _diffrn_reflns_theta_max 25.04 _reflns_number_total 5799 _reflns_number_observed 4597 _reflns_observed_criterion >2sigma(I) _computing_data_collection 'Stoe DIF4' _computing_cell_refinement 'Stoe DIF4' _computing_data_reduction 'local programs' _computing_structure_solution 'Siemens SHELXTL' _computing_structure_refinement 'Siemens SHELXTL' _computing_molecular_graphics 'Siemens SHELXTL' _computing_publication_material 'SHELXTL and local programs' _refine_special_details ; Refinement of F^2^ against ALL reflections. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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 w=1/[\s^2^(Fo^2^)+(0.0319P)^2^+1.0784P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary 'all non-H atoms found by direct methods' _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment ? _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0046(11) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 5799 _refine_ls_number_parameters 440 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0614 _refine_ls_R_factor_obs 0.0455 _refine_ls_wR_factor_all 0.1184 _refine_ls_wR_factor_obs 0.1057 _refine_ls_goodness_of_fit_all 1.016 _refine_ls_goodness_of_fit_obs 1.029 _refine_ls_restrained_S_all 1.016 _refine_ls_restrained_S_obs 1.029 _refine_ls_shift/esd_max 0.000 _refine_ls_shift/esd_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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group C1 C 0.1893(2) 0.28570(15) 0.20215(15) 0.0261(4) Uani 1 d . . O1 O 0.21950(15) 0.25705(11) 0.30086(10) 0.0303(3) Uani 1 d . . H1 H 0.1859 0.3038 0.3347 0.045 Uiso 1 calc R . C2 C 0.17549(19) 0.40943(15) 0.16579(14) 0.0255(4) Uani 1 d . . C3 C 0.0680(2) 0.45569(16) 0.12571(15) 0.0299(4) Uani 1 d . . H3 H 0.0027 0.4101 0.1210 0.036 Uiso 1 calc R . C4 C 0.0534(2) 0.56671(17) 0.09234(15) 0.0334(5) Uani 1 d . . H4 H -0.0203 0.5960 0.0645 0.040 Uiso 1 calc R . C5 C 0.1460(2) 0.63406(17) 0.09974(16) 0.0341(5) Uani 1 d . . H5 H 0.1363 0.7100 0.0776 0.041 Uiso 1 calc R . C6 C 0.2537(2) 0.58998(16) 0.13978(15) 0.0306(4) Uani 1 d . . H6 H 0.3175 0.6367 0.1447 0.037 Uiso 1 calc R . C7 C 0.27086(19) 0.47891(15) 0.17306(14) 0.0263(4) Uani 1 d . . C8 C 0.39201(19) 0.44091(15) 0.21472(15) 0.0253(4) Uani 1 d . . C9 C 0.5143(2) 0.41541(16) 0.14370(16) 0.0310(5) Uani 1 d . . H9 H 0.5163 0.4196 0.0732 0.037 Uiso 1 calc R . C10 C 0.6329(2) 0.38417(17) 0.17360(17) 0.0348(5) Uani 1 d . . H10 H 0.7152 0.3676 0.1239 0.042 Uiso 1 calc R . C11 C 0.6309(2) 0.37729(16) 0.27610(17) 0.0336(5) Uani 1 d . . H11 H 0.7118 0.3561 0.2973 0.040 Uiso 1 calc R . C12 C 0.5098(2) 0.40162(15) 0.34807(16) 0.0290(4) Uani 1 d . . H12 H 0.5087 0.3958 0.4187 0.035 Uiso 1 calc R . C13 C 0.38956(19) 0.43438(14) 0.31929(15) 0.0253(4) Uani 1 d . . C14 C 0.26236(18) 0.46776(15) 0.40134(15) 0.0254(4) Uani 1 d . . O2 O 0.13537(13) 0.43706(11) 0.38893(10) 0.0277(3) Uani 1 d . . H2 H 0.1177 0.4815 0.3376 0.041 Uiso 1 calc R . C15 C 0.3105(2) 0.24638(16) 0.12057(16) 0.0297(4) Uani 1 d . . C16 C 0.3314(2) 0.28729(18) 0.01200(16) 0.0347(5) Uani 1 d . . H16 H 0.2709 0.3419 -0.0113 0.042 Uiso 1 calc R . C17 C 0.4373(2) 0.25058(19) -0.06218(18) 0.0387(5) Uani 1 d . . H17 H 0.4482 0.2788 -0.1354 0.046 Uiso 1 calc R . C18 C 0.5268(2) 0.17294(18) -0.02949(17) 0.0380(5) Uani 1 d . . C19 C 0.5113(2) 0.13135(18) 0.07616(19) 0.0412(5) Uani 1 d . . H19 H 0.5741 0.0783 0.0983 0.049 Uiso 1 calc R . C20 C 0.4012(2) 0.16791(17) 0.15178(18) 0.0377(5) Uani 1 d . . H20 H 0.3895 0.1382 0.2250 0.045 Uiso 1 calc R . O3 O 0.63135(17) 0.14368(14) -0.11056(13) 0.0521(4) Uani 1 d . . C21 C 0.7278(3) 0.0663(2) -0.0819(2) 0.0554(7) Uani 1 d . . H21A H 0.7714 0.0911 -0.0376 0.083 Uiso 1 calc R . H21B H 0.7988 0.0558 -0.1458 0.083 Uiso 1 calc R . H21C H 0.6805 -0.0021 -0.0423 0.083 Uiso 1 calc R . C22 C 0.05447(19) 0.22735(15) 0.21873(15) 0.0263(4) Uani 1 d . . C23 C 0.0260(2) 0.19216(16) 0.13983(16) 0.0325(5) Uani 1 d . . H23 H 0.0919 0.2040 0.0717 0.039 Uiso 1 calc R . C24 C -0.0964(2) 0.14023(17) 0.15860(17) 0.0367(5) Uani 1 d . . H24 H -0.1143 0.1184 0.1029 0.044 Uiso 1 calc R . C25 C -0.1932(2) 0.11971(16) 0.25810(17) 0.0337(5) Uani 1 d . . C26 C -0.1672(2) 0.15365(17) 0.33769(16) 0.0344(5) Uani 1 d . . H26 H -0.2325 0.1401 0.4062 0.041 Uiso 1 calc R . C27 C -0.0453(2) 0.20783(16) 0.31727(16) 0.0315(5) Uani 1 d . . H27 H -0.0296 0.2323 0.3723 0.038 Uiso 1 calc R . O4 O -0.31020(16) 0.06644(13) 0.26848(13) 0.0473(4) Uani 1 d . . C28 C -0.4166(2) 0.0520(2) 0.3666(2) 0.0565(7) Uani 1 d . . H28A H -0.3801 0.0109 0.4236 0.085 Uiso 1 calc R . H28B H -0.4935 0.0127 0.3643 0.085 Uiso 1 calc R . H28C H -0.4496 0.1226 0.3794 0.085 Uiso 1 calc R . C29 C 0.25253(18) 0.40472(15) 0.51516(15) 0.0256(4) Uani 1 d . . C30 C 0.2459(2) 0.29287(16) 0.54224(16) 0.0308(4) Uani 1 d . . H30 H 0.2578 0.2564 0.4881 0.037 Uiso 1 calc R . C31 C 0.2223(2) 0.23271(16) 0.64613(16) 0.0326(5) Uani 1 d . . H31 H 0.2173 0.1563 0.6628 0.039 Uiso 1 calc R . C32 C 0.2061(2) 0.28585(16) 0.72522(15) 0.0301(4) Uani 1 d . . C33 C 0.2171(2) 0.39651(17) 0.69937(16) 0.0332(5) Uani 1 d . . H33 H 0.2101 0.4326 0.7530 0.040 Uiso 1 calc R . C34 C 0.2385(2) 0.45553(16) 0.59572(15) 0.0296(4) Uani 1 d . . H34 H 0.2437 0.5319 0.5794 0.036 Uiso 1 calc R . O5 O 0.17935(17) 0.23585(12) 0.83070(11) 0.0423(4) Uani 1 d . . C35 C 0.1632(4) 0.1225(2) 0.8605(2) 0.0636(8) Uani 1 d . . H35A H 0.2507 0.0883 0.8295 0.095 Uiso 1 calc R . H35B H 0.0907 0.1035 0.8350 0.095 Uiso 1 calc R . H35C H 0.1369 0.0972 0.9377 0.095 Uiso 1 calc R . C36 C 0.26412(19) 0.59002(15) 0.38869(14) 0.0245(4) Uani 1 d . . C37 C 0.3868(2) 0.64197(16) 0.37350(16) 0.0292(4) Uani 1 d . . H37 H 0.4708 0.6018 0.3659 0.035 Uiso 1 calc R . C38 C 0.3884(2) 0.75017(16) 0.36927(17) 0.0327(5) Uani 1 d . . H38 H 0.4728 0.7836 0.3597 0.039 Uiso 1 calc R . C39 C 0.2668(2) 0.81057(15) 0.37899(15) 0.0299(4) Uani 1 d . . C40 C 0.1447(2) 0.76076(16) 0.39329(16) 0.0328(5) Uani 1 d . . H40 H 0.0612 0.8014 0.3991 0.039 Uiso 1 calc R . C41 C 0.1440(2) 0.65104(16) 0.39922(16) 0.0309(5) Uani 1 d . . H41 H 0.0590 0.6174 0.4108 0.037 Uiso 1 calc R . O6 O 0.27932(15) 0.91722(11) 0.37414(13) 0.0413(4) Uani 1 d . . C42 C 0.1567(2) 0.98158(18) 0.3835(2) 0.0456(6) Uani 1 d . . H42A H 0.0875 0.9512 0.4511 0.068 Uiso 1 calc R . H42B H 0.1198 0.9824 0.3253 0.068 Uiso 1 calc R . H42C H 0.1783 1.0553 0.3807 0.068 Uiso 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 C1 0.0302(10) 0.0257(10) 0.0247(10) -0.0063(8) -0.0113(8) -0.0008(8) O1 0.0407(8) 0.0259(7) 0.0288(7) -0.0057(6) -0.0173(6) -0.0012(6) C2 0.0287(10) 0.0259(10) 0.0209(9) -0.0068(8) -0.0053(8) -0.0003(8) C3 0.0321(11) 0.0322(11) 0.0269(10) -0.0083(8) -0.0101(8) -0.0006(8) C4 0.0367(11) 0.0350(12) 0.0278(11) -0.0046(9) -0.0129(9) 0.0058(9) C5 0.0415(12) 0.0254(10) 0.0313(11) -0.0026(8) -0.0093(9) 0.0018(9) C6 0.0340(11) 0.0261(10) 0.0281(10) -0.0044(8) -0.0051(8) -0.0038(8) C7 0.0278(10) 0.0281(10) 0.0212(9) -0.0058(8) -0.0043(8) -0.0020(8) C8 0.0251(10) 0.0214(9) 0.0284(10) -0.0059(8) -0.0060(8) -0.0032(7) C9 0.0318(11) 0.0294(11) 0.0299(11) -0.0097(8) -0.0036(8) -0.0042(8) C10 0.0240(10) 0.0361(12) 0.0426(12) -0.0178(10) -0.0011(9) 0.0003(8) C11 0.0246(10) 0.0337(11) 0.0460(13) -0.0159(9) -0.0116(9) 0.0038(8) C12 0.0273(10) 0.0291(10) 0.0332(11) -0.0112(8) -0.0105(8) 0.0010(8) C13 0.0244(10) 0.0209(9) 0.0302(10) -0.0077(8) -0.0057(8) -0.0029(7) C14 0.0197(9) 0.0299(10) 0.0277(10) -0.0098(8) -0.0058(7) -0.0021(7) O2 0.0233(7) 0.0330(8) 0.0279(7) -0.0075(6) -0.0085(5) -0.0034(6) C15 0.0288(10) 0.0263(10) 0.0367(11) -0.0107(8) -0.0101(8) -0.0043(8) C16 0.0297(11) 0.0407(12) 0.0343(11) -0.0106(9) -0.0083(9) -0.0048(9) C17 0.0334(11) 0.0477(13) 0.0359(12) -0.0141(10) -0.0068(9) -0.0059(10) C18 0.0347(12) 0.0427(13) 0.0367(12) -0.0151(10) -0.0042(9) -0.0094(10) C19 0.0365(12) 0.0313(12) 0.0572(15) -0.0119(10) -0.0167(11) 0.0056(9) C20 0.0378(12) 0.0322(11) 0.0418(12) -0.0069(9) -0.0118(10) -0.0008(9) O3 0.0467(10) 0.0600(11) 0.0452(10) -0.0162(8) -0.0074(8) 0.0086(8) C21 0.0422(14) 0.0573(16) 0.0693(18) -0.0283(14) -0.0117(12) 0.0065(12) C22 0.0283(10) 0.0215(9) 0.0289(10) -0.0040(8) -0.0099(8) 0.0003(8) C23 0.0367(11) 0.0338(11) 0.0265(10) -0.0085(8) -0.0058(9) -0.0086(9) C24 0.0414(12) 0.0379(12) 0.0359(12) -0.0133(9) -0.0130(10) -0.0081(10) C25 0.0303(11) 0.0283(11) 0.0425(12) -0.0083(9) -0.0108(9) -0.0023(8) C26 0.0289(11) 0.0374(12) 0.0311(11) -0.0070(9) -0.0020(9) -0.0004(9) C27 0.0311(11) 0.0363(11) 0.0296(11) -0.0120(9) -0.0103(8) 0.0028(9) O4 0.0352(9) 0.0517(10) 0.0532(10) -0.0148(8) -0.0047(7) -0.0165(7) C28 0.0342(13) 0.0656(17) 0.0613(17) -0.0127(14) -0.0008(12) -0.0162(12) C29 0.0196(9) 0.0293(10) 0.0283(10) -0.0082(8) -0.0065(8) -0.0014(7) C30 0.0344(11) 0.0305(11) 0.0316(11) -0.0122(9) -0.0126(9) 0.0025(8) C31 0.0350(11) 0.0263(10) 0.0366(11) -0.0065(9) -0.0127(9) 0.0020(8) C32 0.0285(10) 0.0345(11) 0.0261(10) -0.0058(8) -0.0083(8) 0.0018(8) C33 0.0393(12) 0.0343(11) 0.0277(10) -0.0120(9) -0.0084(9) -0.0016(9) C34 0.0310(11) 0.0267(10) 0.0316(11) -0.0101(8) -0.0069(8) -0.0017(8) O5 0.0612(10) 0.0336(8) 0.0288(8) -0.0038(6) -0.0131(7) 0.0029(7) C35 0.109(2) 0.0372(14) 0.0352(13) -0.0011(11) -0.0163(14) 0.0044(14) C36 0.0241(9) 0.0286(10) 0.0202(9) -0.0067(8) -0.0050(7) -0.0003(8) C37 0.0232(10) 0.0285(10) 0.0357(11) -0.0090(8) -0.0087(8) 0.0036(8) C38 0.0253(10) 0.0312(11) 0.0404(12) -0.0097(9) -0.0064(9) -0.0037(8) C39 0.0336(11) 0.0234(10) 0.0288(10) -0.0050(8) -0.0050(8) 0.0002(8) C40 0.0253(10) 0.0331(11) 0.0376(11) -0.0110(9) -0.0060(9) 0.0066(8) C41 0.0233(10) 0.0327(11) 0.0364(11) -0.0116(9) -0.0056(8) -0.0012(8) O6 0.0374(8) 0.0256(8) 0.0558(10) -0.0121(7) -0.0054(7) 0.0013(6) C42 0.0476(14) 0.0293(12) 0.0515(14) -0.0107(10) -0.0047(11) 0.0084(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 C1 O1 1.429(2) . ? C1 C15 1.536(3) . ? C1 C22 1.545(3) . ? C1 C2 1.545(3) . ? C2 C3 1.392(3) . ? C2 C7 1.416(3) . ? C3 C4 1.390(3) . ? C4 C5 1.376(3) . ? C5 C6 1.386(3) . ? C6 C7 1.394(3) . ? C7 C8 1.505(3) . ? C8 C9 1.396(3) . ? C8 C13 1.409(3) . ? C9 C10 1.385(3) . ? C10 C11 1.381(3) . ? C11 C12 1.389(3) . ? C12 C13 1.396(3) . ? C13 C14 1.542(3) . ? C14 O2 1.453(2) . ? C14 C36 1.537(3) . ? C14 C29 1.537(3) . ? C15 C20 1.381(3) . ? C15 C16 1.399(3) . ? C16 C17 1.379(3) . ? C17 C18 1.373(3) . ? C18 C19 1.372(3) . ? C18 O3 1.387(3) . ? C19 C20 1.412(3) . ? O3 C21 1.403(3) . ? C22 C23 1.391(3) . ? C22 C27 1.392(3) . ? C23 C24 1.383(3) . ? C24 C25 1.388(3) . ? C25 O4 1.375(3) . ? C25 C26 1.379(3) . ? C26 C27 1.390(3) . ? O4 C28 1.421(3) . ? C29 C30 1.390(3) . ? C29 C34 1.391(3) . ? C30 C31 1.390(3) . ? C31 C32 1.389(3) . ? C32 O5 1.372(2) . ? C32 C33 1.379(3) . ? C33 C34 1.386(3) . ? O5 C35 1.417(3) . ? C36 C41 1.382(3) . ? C36 C37 1.398(3) . ? C37 C38 1.378(3) . ? C38 C39 1.390(3) . ? C39 O6 1.370(2) . ? C39 C40 1.382(3) . ? C40 C41 1.392(3) . ? O6 C42 1.425(3) . ? 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 C15 107.70(15) . . ? O1 C1 C22 107.20(15) . . ? C15 C1 C22 110.50(15) . . ? O1 C1 C2 109.93(15) . . ? C15 C1 C2 109.24(15) . . ? C22 C1 C2 112.16(15) . . ? C3 C2 C7 118.13(18) . . ? C3 C2 C1 120.80(17) . . ? C7 C2 C1 121.07(17) . . ? C4 C3 C2 121.90(19) . . ? C5 C4 C3 119.85(19) . . ? C4 C5 C6 119.35(19) . . ? C5 C6 C7 121.80(19) . . ? C6 C7 C2 118.96(18) . . ? C6 C7 C8 116.81(17) . . ? C2 C7 C8 124.23(17) . . ? C9 C8 C13 118.99(18) . . ? C9 C8 C7 117.44(17) . . ? C13 C8 C7 123.51(17) . . ? C10 C9 C8 121.58(19) . . ? C11 C10 C9 119.64(18) . . ? C10 C11 C12 119.57(19) . . ? C11 C12 C13 121.71(19) . . ? C12 C13 C8 118.50(17) . . ? C12 C13 C14 118.68(17) . . ? C8 C13 C14 122.74(17) . . ? O2 C14 C36 110.32(15) . . ? O2 C14 C29 102.08(14) . . ? C36 C14 C29 111.58(15) . . ? O2 C14 C13 110.52(15) . . ? C36 C14 C13 109.70(15) . . ? C29 C14 C13 112.44(16) . . ? C20 C15 C16 117.60(19) . . ? C20 C15 C1 121.20(19) . . ? C16 C15 C1 121.19(18) . . ? C17 C16 C15 121.9(2) . . ? C18 C17 C16 119.6(2) . . ? C19 C18 C17 120.6(2) . . ? C19 C18 O3 124.6(2) . . ? C17 C18 O3 114.8(2) . . ? C18 C19 C20 119.6(2) . . ? C15 C20 C19 120.7(2) . . ? C18 O3 C21 117.4(2) . . ? C23 C22 C27 117.09(18) . . ? C23 C22 C1 123.53(17) . . ? C27 C22 C1 119.39(17) . . ? C24 C23 C22 121.36(19) . . ? C23 C24 C25 120.5(2) . . ? O4 C25 C26 125.02(19) . . ? O4 C25 C24 115.78(19) . . ? C26 C25 C24 119.19(19) . . ? C25 C26 C27 119.74(19) . . ? C26 C27 C22 122.05(19) . . ? C25 O4 C28 117.31(19) . . ? C30 C29 C34 117.63(18) . . ? C30 C29 C14 119.72(17) . . ? C34 C29 C14 122.43(17) . . ? C29 C30 C31 121.99(19) . . ? C32 C31 C30 119.06(19) . . ? O5 C32 C33 115.68(18) . . ? O5 C32 C31 124.57(19) . . ? C33 C32 C31 119.76(18) . . ? C32 C33 C34 120.50(19) . . ? C33 C34 C29 121.00(19) . . ? C32 O5 C35 117.20(18) . . ? C41 C36 C37 117.66(18) . . ? C41 C36 C14 121.52(17) . . ? C37 C36 C14 120.67(16) . . ? C38 C37 C36 121.40(18) . . ? C37 C38 C39 120.19(19) . . ? O6 C39 C40 125.10(18) . . ? O6 C39 C38 115.67(18) . . ? C40 C39 C38 119.23(18) . . ? C39 C40 C41 120.05(18) . . ? C36 C41 C40 121.46(18) . . ? C39 O6 C42 117.13(17) . . ? _refine_diff_density_max 0.668 _refine_diff_density_min -0.258 _refine_diff_density_rms 0.041 data_hm14 _database_code_CSD 190261 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C40 H34 O4' _chemical_formula_weight 578.67 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0181 0.0091 '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' 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P2(1)/n 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' _cell_length_a 13.017(3) _cell_length_b 16.298(6) _cell_length_c 15.554(4) _cell_angle_alpha 90.00 _cell_angle_beta 110.699(18) _cell_angle_gamma 90.00 _cell_volume 3086.7(15) _cell_formula_units_Z 4 _cell_measurement_temperature 160(2) _cell_measurement_reflns_used 36 _cell_measurement_theta_min 30.91 _cell_measurement_theta_max 49.35 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.38 _exptl_crystal_size_min 0.23 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.245 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1224 _exptl_absorpt_coefficient_mu 0.626 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.613 _exptl_absorpt_correction_T_max 0.920 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 160(2) _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Stoe-Siemens diffractometer' _diffrn_measurement_method '\w/\q scans with on-line profile fitting' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 5 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 60 _diffrn_standards_decay_% 2 _diffrn_reflns_number 7745 _diffrn_reflns_av_R_equivalents 0.0861 _diffrn_reflns_av_sigmaI/netI 0.1068 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 3.82 _diffrn_reflns_theta_max 54.99 _reflns_number_total 3881 _reflns_number_gt 1597 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Stoe DIF4' _computing_cell_refinement 'Stoe DIF4' _computing_data_reduction 'local programs' _computing_structure_solution 'Siemens SHELXTL' _computing_structure_refinement 'Siemens SHELXTL' _computing_molecular_graphics 'Siemens SHELXTL' _computing_publication_material 'SHELXTL and local programs' _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^)+(0.1110P)^2^+0.7230P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens 'geom except H1&2 coords freely refined' _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0008(3) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 3881 _refine_ls_number_parameters 469 _refine_ls_number_restraints 265 _refine_ls_R_factor_all 0.1856 _refine_ls_R_factor_gt 0.0840 _refine_ls_wR_factor_ref 0.2787 _refine_ls_wR_factor_gt 0.2060 _refine_ls_goodness_of_fit_ref 1.023 _refine_ls_restrained_S_all 1.010 _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 0.5548(4) -0.1071(5) 0.2162(4) 0.127(3) Uani 1 1 d D . . H1 H 0.593(7) -0.136(6) 0.267(6) 0.153 Uiso 1 1 d D . . H2 H 0.657(8) -0.021(5) 0.236(7) 0.153 Uiso 1 1 d D . . C1 C 0.4512(5) -0.0901(7) 0.2284(6) 0.104(3) Uani 1 1 d . . . C2 C 0.4628(5) -0.0063(5) 0.2770(5) 0.077(2) Uani 1 1 d . . . C3 C 0.3805(5) 0.0504(6) 0.2459(5) 0.092(2) Uani 1 1 d . . . H3 H 0.3166 0.0366 0.1951 0.111 Uiso 1 1 calc R . . C4 C 0.3866(6) 0.1262(6) 0.2851(6) 0.101(3) Uani 1 1 d . . . H4 H 0.3276 0.1640 0.2617 0.121 Uiso 1 1 calc R . . C5 C 0.4781(6) 0.1473(5) 0.3582(5) 0.090(2) Uani 1 1 d . . . H5 H 0.4843 0.1999 0.3859 0.108 Uiso 1 1 calc R . . C6 C 0.5616(5) 0.0900(5) 0.3905(4) 0.077(2) Uani 1 1 d . . . H6 H 0.6249 0.1039 0.4418 0.092 Uiso 1 1 calc R . . C7 C 0.5565(4) 0.0144(5) 0.3518(4) 0.0668(18) Uani 1 1 d . . . C8 C 0.6494(5) -0.0431(4) 0.3993(5) 0.0722(19) Uani 1 1 d . . . C9 C 0.6332(5) -0.0932(5) 0.4633(6) 0.091(2) Uani 1 1 d . . . H9 H 0.5649 -0.0905 0.4724 0.109 Uiso 1 1 calc R . . C10 C 0.7123(6) -0.1487(5) 0.5164(6) 0.105(3) Uani 1 1 d . . . H10 H 0.6984 -0.1821 0.5611 0.126 Uiso 1 1 calc R . . C11 C 0.8114(6) -0.1539(5) 0.5022(7) 0.117(3) Uani 1 1 d . . . H11 H 0.8660 -0.1922 0.5352 0.140 Uiso 1 1 calc R . . C12 C 0.8283(5) -0.1017(5) 0.4388(6) 0.091(2) Uani 1 1 d . . . H12 H 0.8971 -0.1040 0.4305 0.109 Uiso 1 1 calc R . . C13 C 0.7509(5) -0.0462(4) 0.3866(5) 0.0744(19) Uani 1 1 d . . . C14 C 0.7794(5) 0.0146(6) 0.3240(5) 0.090(3) Uani 1 1 d . A . O2 O 0.6879(4) 0.0293(5) 0.2408(4) 0.118(2) Uani 1 1 d D . . C15 C 0.4263(6) -0.1570(7) 0.2845(6) 0.099(3) Uani 1 1 d . . . C16 C 0.3603(6) -0.1432(6) 0.3372(6) 0.108(3) Uani 1 1 d . . . H16 H 0.3316 -0.0900 0.3398 0.129 Uiso 1 1 calc R . . C17 C 0.3365(6) -0.2092(8) 0.3866(6) 0.114(3) Uani 1 1 d . . . H17 H 0.2916 -0.1986 0.4221 0.137 Uiso 1 1 calc R . . C19 C 0.4380(9) -0.3015(8) 0.3325(9) 0.133(4) Uani 1 1 d . . . H19 H 0.4653 -0.3551 0.3295 0.159 Uiso 1 1 calc R . . C20 C 0.4622(6) -0.2386(9) 0.2831(7) 0.121(4) Uani 1 1 d . . . H20 H 0.5050 -0.2509 0.2463 0.145 Uiso 1 1 calc R . . C18 C 0.3753(7) -0.2881(9) 0.3858(8) 0.130(3) Uani 1 1 d DU . . O3 O 0.3442(8) -0.3421(6) 0.4435(7) 0.227(6) Uani 1 1 d DU . . C21 C 0.3835(13) -0.4173(10) 0.4489(13) 0.263(8) Uani 1 1 d DU . . H21A H 0.3681 -0.4390 0.3869 0.394 Uiso 1 1 calc R . . H21B H 0.3485 -0.4523 0.4819 0.394 Uiso 1 1 calc R . . H21C H 0.4630 -0.4164 0.4821 0.394 Uiso 1 1 calc R . . C22 C 0.3644(6) -0.0896(6) 0.1308(6) 0.114(3) Uani 1 1 d . . . C23 C 0.3869(8) -0.0438(11) 0.0639(7) 0.221(8) Uani 1 1 d . . . H23 H 0.4524 -0.0124 0.0797 0.265 Uiso 1 1 calc R . . C24 C 0.3142(10) -0.0446(11) -0.0245(7) 0.229(9) Uani 1 1 d . . . H24 H 0.3303 -0.0133 -0.0697 0.275 Uiso 1 1 calc R . . C25 C 0.2197(10) -0.0885(10) -0.0496(9) 0.163(6) Uani 1 1 d . . . H25 H 0.1710 -0.0901 -0.1117 0.195 Uiso 1 1 calc R . . C26 C 0.1981(9) -0.1289(8) 0.0151(10) 0.158(5) Uani 1 1 d . . . H26 H 0.1297 -0.1567 -0.0007 0.190 Uiso 1 1 calc R . . C27 C 0.2701(6) -0.1330(6) 0.1055(7) 0.127(3) Uani 1 1 d . . . H27 H 0.2532 -0.1660 0.1491 0.153 Uiso 1 1 calc R . . C28 C 0.8129(5) 0.0950(6) 0.3698(7) 0.092(2) Uani 1 1 d DU . . C29 C 0.7845(18) 0.1550(11) 0.2975(11) 0.100(5) Uani 0.545(9) 1 d PDU A 1 H29 H 0.7456 0.1424 0.2347 0.119 Uiso 0.545(9) 1 calc PR A 1 C30 C 0.8219(13) 0.2375(11) 0.3309(12) 0.094(4) Uani 0.545(9) 1 d PDU A 1 H30 H 0.8120 0.2817 0.2889 0.113 Uiso 0.545(9) 1 calc PR A 1 C31 C 0.870(4) 0.2500(13) 0.4215(14) 0.086(5) Uani 0.545(9) 1 d PDU A 1 C32 C 0.8931(17) 0.1882(10) 0.4870(13) 0.085(4) Uani 0.545(9) 1 d PDU A 1 H32 H 0.9308 0.2010 0.5498 0.102 Uiso 0.545(9) 1 calc PR A 1 C33 C 0.861(4) 0.1074(13) 0.4615(9) 0.087(5) Uani 0.545(9) 1 d PDU A 1 H33 H 0.8721 0.0644 0.5051 0.104 Uiso 0.545(9) 1 calc PR A 1 O4 O 0.9079(8) 0.3295(7) 0.4453(7) 0.105(4) Uani 0.545(9) 1 d PDU A 1 C34 C 0.957(3) 0.3472(14) 0.5363(14) 0.132(9) Uani 0.545(9) 1 d PDU A 1 H34A H 0.9809 0.4047 0.5434 0.198 Uiso 0.545(9) 1 calc PR A 1 H34B H 1.0215 0.3116 0.5629 0.198 Uiso 0.545(9) 1 calc PR A 1 H34C H 0.9054 0.3380 0.5680 0.198 Uiso 0.545(9) 1 calc PR A 1 C29X C 0.817(2) 0.1771(11) 0.3359(15) 0.089(5) Uani 0.455(9) 1 d PDU A 2 H29X H 0.7847 0.1883 0.2720 0.106 Uiso 0.455(9) 1 calc PR A 2 C30X C 0.871(4) 0.2430(17) 0.3997(17) 0.092(7) Uani 0.455(9) 1 d PDU A 2 H30X H 0.8804 0.2943 0.3742 0.110 Uiso 0.455(9) 1 calc PR A 2 C31X C 0.9093(16) 0.2361(11) 0.4912(14) 0.085(5) Uani 0.455(9) 1 d PDU A 2 C32X C 0.8984(18) 0.1601(11) 0.5275(13) 0.083(4) Uani 0.455(9) 1 d PDU A 2 H32X H 0.9189 0.1531 0.5920 0.099 Uiso 0.455(9) 1 calc PR A 2 C33X C 0.856(5) 0.0931(12) 0.4671(10) 0.090(7) Uani 0.455(9) 1 d PDU A 2 H33X H 0.8573 0.0412 0.4951 0.108 Uiso 0.455(9) 1 calc PR A 2 O4X O 0.951(2) 0.3083(9) 0.5409(13) 0.110(5) Uani 0.455(9) 1 d PDU A 2 C34X C 1.0154(14) 0.3005(13) 0.6308(12) 0.128(8) Uani 0.455(9) 1 d PDU A 2 H34D H 1.0393 0.3550 0.6570 0.192 Uiso 0.455(9) 1 calc PR A 2 H34E H 1.0798 0.2670 0.6358 0.192 Uiso 0.455(9) 1 calc PR A 2 H34F H 0.9734 0.2740 0.6644 0.192 Uiso 0.455(9) 1 calc PR A 2 C35 C 0.8730(5) -0.0188(6) 0.2930(5) 0.104(3) Uani 1 1 d . . . C36 C 0.8510(7) -0.0860(9) 0.2359(8) 0.177(5) Uani 1 1 d . A . H36 H 0.7804 -0.1106 0.2178 0.212 Uiso 1 1 calc R . . C37 C 0.9294(9) -0.1189(9) 0.2038(9) 0.211(7) Uani 1 1 d . . . H37 H 0.9110 -0.1634 0.1616 0.254 Uiso 1 1 calc R A . C38 C 1.0333(9) -0.0866(10) 0.2335(8) 0.182(6) Uani 1 1 d . A . H38 H 1.0884 -0.1097 0.2138 0.219 Uiso 1 1 calc R . . C39 C 1.0562(7) -0.0225(8) 0.2903(7) 0.130(4) Uani 1 1 d . . . H39 H 1.1280 0.0003 0.3108 0.156 Uiso 1 1 calc R A . C40 C 0.9755(5) 0.0122(6) 0.3205(5) 0.098(3) Uani 1 1 d . A . H40 H 0.9937 0.0581 0.3608 0.118 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 0.065(3) 0.189(7) 0.132(5) -0.078(5) 0.039(3) 0.000(3) C1 0.055(4) 0.162(9) 0.103(6) -0.039(7) 0.036(4) -0.012(5) C2 0.057(4) 0.097(6) 0.078(4) -0.016(5) 0.025(3) -0.006(4) C3 0.058(4) 0.133(8) 0.079(5) -0.008(5) 0.016(3) 0.012(5) C4 0.077(5) 0.117(8) 0.103(6) 0.014(6) 0.026(5) 0.018(5) C5 0.069(4) 0.093(6) 0.101(5) -0.007(5) 0.022(4) 0.000(4) C6 0.063(4) 0.102(6) 0.064(4) 0.001(5) 0.021(3) -0.002(4) C7 0.052(3) 0.084(6) 0.069(4) -0.015(4) 0.026(3) -0.001(3) C8 0.060(4) 0.080(5) 0.079(4) 0.005(4) 0.027(3) -0.009(4) C9 0.057(4) 0.093(6) 0.117(6) 0.003(5) 0.025(4) -0.001(4) C10 0.083(5) 0.085(6) 0.155(7) 0.038(6) 0.052(5) 0.000(4) C11 0.067(5) 0.094(7) 0.182(9) 0.034(7) 0.035(5) -0.006(4) C12 0.061(4) 0.073(5) 0.141(7) 0.003(5) 0.040(4) 0.001(4) C13 0.052(4) 0.073(5) 0.092(5) -0.010(4) 0.017(3) 0.002(4) C14 0.045(3) 0.143(8) 0.083(5) 0.001(5) 0.023(3) -0.004(4) O2 0.057(3) 0.210(7) 0.087(3) 0.029(4) 0.024(3) 0.010(3) C15 0.060(4) 0.123(9) 0.102(6) -0.044(6) 0.016(4) -0.003(5) C16 0.073(5) 0.106(8) 0.150(8) -0.029(7) 0.046(5) -0.021(5) C17 0.082(5) 0.133(9) 0.126(7) -0.050(7) 0.035(5) -0.021(6) C19 0.098(7) 0.113(10) 0.146(10) -0.034(8) -0.006(7) 0.007(7) C20 0.073(5) 0.142(11) 0.129(8) -0.037(8) 0.012(5) 0.010(6) C18 0.064(5) 0.146(11) 0.154(9) -0.062(7) 0.007(5) -0.010(6) O3 0.194(8) 0.130(7) 0.241(10) 0.051(7) -0.067(7) -0.072(7) C21 0.240(16) 0.200(12) 0.299(19) 0.019(15) 0.033(14) -0.044(13) C22 0.067(4) 0.171(9) 0.104(6) -0.064(7) 0.031(4) -0.022(5) C23 0.113(7) 0.48(3) 0.088(7) -0.035(10) 0.053(6) -0.100(11) C24 0.128(8) 0.49(3) 0.082(7) -0.058(11) 0.047(6) -0.086(12) C25 0.129(9) 0.240(17) 0.100(8) -0.066(10) 0.019(7) -0.005(10) C26 0.109(7) 0.172(13) 0.139(10) -0.033(9) -0.023(8) -0.011(7) C27 0.078(5) 0.152(9) 0.125(7) -0.018(7) 0.004(5) 0.003(6) C28 0.056(4) 0.096(6) 0.131(5) 0.012(5) 0.043(4) 0.004(4) C29 0.076(12) 0.108(10) 0.121(9) -0.003(7) 0.043(9) -0.012(9) C30 0.078(9) 0.110(9) 0.102(8) 0.001(7) 0.042(7) -0.012(9) C31 0.087(10) 0.095(8) 0.087(9) 0.010(7) 0.046(10) 0.004(9) C32 0.061(8) 0.075(9) 0.125(9) 0.018(7) 0.040(9) -0.007(10) C33 0.043(9) 0.085(9) 0.134(8) -0.009(9) 0.033(9) -0.023(11) O4 0.126(7) 0.097(7) 0.097(7) 0.011(6) 0.046(6) -0.018(6) C34 0.172(18) 0.10(2) 0.108(10) 0.010(12) 0.035(12) -0.03(2) C29X 0.068(13) 0.091(11) 0.127(10) -0.009(8) 0.060(10) -0.024(11) C30X 0.073(11) 0.103(9) 0.107(9) 0.010(9) 0.042(14) -0.014(10) C31X 0.059(9) 0.076(9) 0.108(9) 0.021(8) 0.016(8) -0.012(10) C32X 0.060(9) 0.061(9) 0.131(10) 0.014(7) 0.039(11) -0.001(9) C33X 0.057(16) 0.068(9) 0.137(8) -0.006(8) 0.023(12) 0.008(11) O4X 0.125(10) 0.068(10) 0.124(9) 0.019(8) 0.029(8) -0.008(10) C34X 0.096(12) 0.119(17) 0.135(12) -0.026(12) -0.002(10) -0.016(11) C35 0.055(4) 0.157(9) 0.094(6) -0.013(6) 0.021(4) -0.003(5) C36 0.075(6) 0.251(14) 0.194(10) -0.118(11) 0.035(6) -0.006(7) C37 0.097(7) 0.33(2) 0.201(11) -0.119(12) 0.044(7) 0.036(10) C38 0.109(8) 0.309(19) 0.136(9) -0.068(11) 0.052(7) 0.033(10) C39 0.076(5) 0.208(13) 0.120(7) -0.001(8) 0.053(5) 0.007(6) C40 0.063(4) 0.160(8) 0.083(5) 0.007(5) 0.038(4) 0.002(5) _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 1.454(8) . ? C1 C15 1.501(12) . ? C1 C22 1.539(11) . ? C1 C2 1.542(10) . ? C2 C3 1.367(9) . ? C2 C7 1.397(8) . ? C3 C4 1.367(10) . ? C4 C5 1.369(10) . ? C5 C6 1.386(9) . ? C6 C7 1.362(9) . ? C7 C8 1.501(9) . ? C8 C9 1.362(9) . ? C8 C13 1.404(8) . ? C9 C10 1.399(9) . ? C10 C11 1.386(10) . ? C11 C12 1.377(11) . ? C12 C13 1.384(9) . ? C13 C14 1.525(10) . ? C14 O2 1.435(8) . ? C14 C28 1.482(11) . ? C14 C35 1.558(10) . ? C15 C16 1.400(11) . ? C15 C20 1.412(12) . ? C16 C17 1.419(12) . ? C17 C18 1.384(14) . ? C19 C18 1.370(14) . ? C19 C20 1.384(13) . ? C18 O3 1.414(13) . ? O3 C21 1.318(14) . ? C22 C27 1.349(11) . ? C22 C23 1.392(14) . ? C23 C24 1.367(13) . ? C24 C25 1.356(15) . ? C25 C26 1.314(15) . ? C26 C27 1.389(13) . ? C28 C33 1.355(14) . ? C28 C33X 1.416(16) . ? C28 C29 1.437(15) . ? C28 C29X 1.447(16) . ? C29 C30 1.461(19) . ? C30 C31 1.34(3) . ? C31 C32 1.39(2) . ? C31 O4 1.388(17) . ? C32 C33 1.395(15) . ? O4 C34 1.362(18) . ? C29X C30X 1.46(2) . ? C30X C31X 1.34(3) . ? C31X C32X 1.39(2) . ? C31X O4X 1.407(17) . ? C32X C33X 1.417(16) . ? O4X C34X 1.358(19) . ? C35 C40 1.347(9) . ? C35 C36 1.375(12) . ? C36 C37 1.393(13) . ? C37 C38 1.371(15) . ? C38 C39 1.333(14) . ? C39 C40 1.411(11) . ? 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 C15 109.8(8) . . ? O1 C1 C22 105.3(6) . . ? C15 C1 C22 110.1(7) . . ? O1 C1 C2 107.4(6) . . ? C15 C1 C2 111.2(7) . . ? C22 C1 C2 112.9(8) . . ? C3 C2 C7 118.4(7) . . ? C3 C2 C1 119.8(7) . . ? C7 C2 C1 121.8(6) . . ? C2 C3 C4 122.6(7) . . ? C3 C4 C5 119.6(8) . . ? C4 C5 C6 118.2(8) . . ? C7 C6 C5 122.7(6) . . ? C6 C7 C2 118.5(6) . . ? C6 C7 C8 116.2(6) . . ? C2 C7 C8 125.0(7) . . ? C9 C8 C13 118.5(6) . . ? C9 C8 C7 115.4(6) . . ? C13 C8 C7 126.0(6) . . ? C8 C9 C10 123.2(7) . . ? C11 C10 C9 118.5(8) . . ? C12 C11 C10 118.0(7) . . ? C11 C12 C13 123.8(7) . . ? C12 C13 C8 117.9(7) . . ? C12 C13 C14 120.6(6) . . ? C8 C13 C14 121.3(6) . . ? O2 C14 C28 107.2(7) . . ? O2 C14 C13 111.8(5) . . ? C28 C14 C13 111.4(6) . . ? O2 C14 C35 105.7(6) . . ? C28 C14 C35 109.2(6) . . ? C13 C14 C35 111.3(7) . . ? C16 C15 C20 115.8(10) . . ? C16 C15 C1 121.8(9) . . ? C20 C15 C1 122.3(9) . . ? C15 C16 C17 119.5(9) . . ? C18 C17 C16 123.4(10) . . ? C18 C19 C20 121.3(12) . . ? C19 C20 C15 123.2(11) . . ? C19 C18 C17 116.8(13) . . ? C19 C18 O3 130.5(14) . . ? C17 C18 O3 112.7(12) . . ? C21 O3 C18 115.4(15) . . ? C27 C22 C23 118.3(9) . . ? C27 C22 C1 124.0(10) . . ? C23 C22 C1 117.7(8) . . ? C24 C23 C22 119.5(10) . . ? C25 C24 C23 122.0(13) . . ? C26 C25 C24 117.5(12) . . ? C25 C26 C27 123.3(12) . . ? C22 C27 C26 119.3(11) . . ? C33 C28 C33X 10.6(15) . . ? C33 C28 C29 128.2(13) . . ? C33X C28 C29 138.3(13) . . ? C33 C28 C29X 100.6(13) . . ? C33X C28 C29X 111.0(14) . . ? C29 C28 C29X 28.0(8) . . ? C33 C28 C14 125.9(11) . . ? C33X C28 C14 115.7(10) . . ? C29 C28 C14 105.9(10) . . ? C29X C28 C14 133.2(12) . . ? C28 C29 C30 112.7(14) . . ? C31 C30 C29 119.2(17) . . ? C30 C31 C32 124.0(18) . . ? C30 C31 O4 114.4(19) . . ? C32 C31 O4 121.2(18) . . ? C31 C32 C33 120.8(17) . . ? C28 C33 C32 114.8(15) . . ? C34 O4 C31 117.8(15) . . ? C28 C29X C30X 120.2(18) . . ? C31X C30X C29X 125(2) . . ? C30X C31X C32X 117.1(18) . . ? C30X C31X O4X 116(2) . . ? C32X C31X O4X 126.7(18) . . ? C31X C32X C33X 119.3(18) . . ? C28 C33X C32X 127.3(17) . . ? C34X O4X C31X 117.7(16) . . ? C40 C35 C36 117.5(8) . . ? C40 C35 C14 124.4(8) . . ? C36 C35 C14 118.1(7) . . ? C35 C36 C37 121.8(10) . . ? C38 C37 C36 119.5(12) . . ? C39 C38 C37 119.1(10) . . ? C38 C39 C40 121.2(9) . . ? C35 C40 C39 120.9(9) . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 54.99 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.162 _refine_diff_density_min -0.237 _refine_diff_density_rms 0.044