# Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is (c) The Royal Society of Chemistry 2009 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_theod24 _database_code_depnum_ccdc_archive 'CCDC 614936' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common FRB961 _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C24 H28 O5' _chemical_formula_weight 396.46 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 10.5010(10) _cell_length_b 14.3480(14) _cell_length_c 14.6990(14) _cell_angle_alpha 112.0840(10) _cell_angle_beta 90.4770(10) _cell_angle_gamma 104.1960(10) _cell_volume 1977.0(3) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 5848 _cell_measurement_theta_min 2.37 _cell_measurement_theta_max 28.11 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_diffrn 1.332 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 848 _exptl_absorpt_coefficient_mu 0.092 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9818 _exptl_absorpt_correction_T_max 0.9908 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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_reflns_number 20632 _diffrn_reflns_av_R_equivalents 0.0209 _diffrn_reflns_av_sigmaI/netI 0.0296 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.21 _diffrn_reflns_theta_max 28.22 _reflns_number_total 8823 _reflns_number_gt 7550 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution SIR-2004 _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ORTEP-32 _computing_publication_material WinGX _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^ > 2\s(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^)+(0.0702P)^2^+1.0377P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_number_reflns 8823 _refine_ls_number_parameters 533 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0583 _refine_ls_R_factor_gt 0.0502 _refine_ls_wR_factor_ref 0.1345 _refine_ls_wR_factor_gt 0.1287 _refine_ls_goodness_of_fit_ref 1.021 _refine_ls_restrained_S_all 1.021 _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 C1 C 0.74038(17) 1.06895(12) 0.99206(12) 0.0227(3) Uani 1 1 d . . . H1 H 0.6573 1.0721 1.0163 0.027 Uiso 1 1 calc R . . C2 C 0.84879(18) 1.15349(13) 1.03358(12) 0.0257(3) Uani 1 1 d . . . H2 H 0.8408 1.2143 1.0867 0.031 Uiso 1 1 calc R . . C3 C 0.97045(17) 1.14944(13) 0.99733(12) 0.0261(3) Uani 1 1 d . . . H3 H 1.0451 1.2080 1.0258 0.031 Uiso 1 1 calc R . . C4 C 0.98388(16) 1.06186(13) 0.92091(12) 0.0239(3) Uani 1 1 d . . . H4 H 1.0670 1.0600 0.8963 0.029 Uiso 1 1 calc R . . C5 C 0.87460(16) 0.97584(12) 0.87988(11) 0.0202(3) Uani 1 1 d . . . C6 C 0.75115(16) 0.97830(12) 0.91443(11) 0.0202(3) Uani 1 1 d . . . C7 C 0.63746(16) 0.88566(12) 0.87303(12) 0.0219(3) Uani 1 1 d . . . C8 C 0.67306(15) 0.78727(12) 0.80647(11) 0.0197(3) Uani 1 1 d . . . H8 H 0.7138 0.7611 0.8505 0.024 Uiso 1 1 calc R . . C9 C 0.77934(15) 0.81614(12) 0.74379(11) 0.0188(3) Uani 1 1 d . . . C10 C 0.73333(15) 0.85289(12) 0.66633(11) 0.0202(3) Uani 1 1 d . . . H10 H 0.7355 0.9285 0.6973 0.024 Uiso 1 1 calc R . . C11 C 0.59165(16) 0.78523(12) 0.62446(12) 0.0237(3) Uani 1 1 d . . . H11A H 0.5757 0.7745 0.5543 0.028 Uiso 1 1 calc R . . H11B H 0.5277 0.8213 0.6615 0.028 Uiso 1 1 calc R . . C12 C 0.57120(16) 0.67837(12) 0.63291(12) 0.0228(3) Uani 1 1 d . . . H12 H 0.4920 0.6257 0.5886 0.027 Uiso 1 1 calc R . . C13 C 0.55583(16) 0.69814(12) 0.74224(12) 0.0218(3) Uani 1 1 d . . . H13 H 0.4717 0.7181 0.7594 0.026 Uiso 1 1 calc R . . C14 C 0.43442(18) 0.53036(14) 0.72900(14) 0.0302(4) Uani 1 1 d . . . H14A H 0.4214 0.5025 0.6567 0.045 Uiso 1 1 calc R . . H14B H 0.3616 0.5602 0.7557 0.045 Uiso 1 1 calc R . . H14C H 0.4362 0.4739 0.7508 0.045 Uiso 1 1 calc R . . C15 C 0.69477(17) 0.64091(12) 0.61135(12) 0.0223(3) Uani 1 1 d . . . C16 C 0.82269(16) 0.72198(12) 0.67460(12) 0.0211(3) Uani 1 1 d . . . C17 C 0.83968(17) 0.83565(12) 0.59221(12) 0.0233(3) Uani 1 1 d . . . C18 C 0.7866(2) 0.78918(14) 0.48366(13) 0.0313(4) Uani 1 1 d . . . H18A H 0.7242 0.7206 0.4677 0.047 Uiso 1 1 calc R . . H18B H 0.8600 0.7815 0.4432 0.047 Uiso 1 1 calc R . . H18C H 0.7413 0.8355 0.4700 0.047 Uiso 1 1 calc R . . C19 C 0.94864(18) 0.93561(13) 0.61392(14) 0.0292(4) Uani 1 1 d . . . H19A H 1.0217 0.9195 0.5752 0.044 Uiso 1 1 calc R . . H19B H 0.9808 0.9672 0.6845 0.044 Uiso 1 1 calc R . . H19C H 0.9137 0.9846 0.5960 0.044 Uiso 1 1 calc R . . C20 C 0.90333(17) 0.67854(14) 0.72710(13) 0.0262(3) Uani 1 1 d . . . H20A H 0.9681 0.7380 0.7782 0.031 Uiso 1 1 calc R . . H20B H 0.8430 0.6417 0.7616 0.031 Uiso 1 1 calc R . . C35 C 0.60115(15) 1.17691(12) 0.86778(12) 0.0207(3) Uani 1 1 d . . . H35A H 0.6378 1.2074 0.9381 0.025 Uiso 1 1 calc R . . H35B H 0.6551 1.1311 0.8295 0.025 Uiso 1 1 calc R . . C21 C 0.97614(17) 0.60590(14) 0.66418(13) 0.0274(4) Uani 1 1 d . . . H21 H 0.9987 0.6120 0.6038 0.033 Uiso 1 1 calc R . . C22 C 1.01260(18) 0.53279(14) 0.68513(14) 0.0314(4) Uani 1 1 d . . . C23 C 0.9823(3) 0.5134(2) 0.77642(19) 0.0576(7) Uani 1 1 d . . . H23A H 0.9161 0.4462 0.7589 0.086 Uiso 1 1 calc R . . H23B H 0.9476 0.5693 0.8214 0.086 Uiso 1 1 calc R . . H23C H 1.0631 0.5120 0.8090 0.086 Uiso 1 1 calc R . . C24 C 1.08205(19) 0.46027(15) 0.61651(15) 0.0354(4) Uani 1 1 d . . . H24A H 1.1037 0.4809 0.5609 0.053 Uiso 1 1 calc R . . H24B H 1.0245 0.3888 0.5918 0.053 Uiso 1 1 calc R . . H24C H 1.1636 0.4635 0.6519 0.053 Uiso 1 1 calc R . . C25 C 0.72074(16) 1.16284(13) 0.52237(12) 0.0233(3) Uani 1 1 d . . . H25 H 0.7466 1.0997 0.4977 0.028 Uiso 1 1 calc R . . C26 C 0.77512(17) 1.24150(13) 0.49071(12) 0.0265(3) Uani 1 1 d . . . H26 H 0.8384 1.2327 0.4445 0.032 Uiso 1 1 calc R . . C27 C 0.73677(17) 1.33396(13) 0.52679(13) 0.0262(3) Uani 1 1 d . . . H27 H 0.7739 1.3878 0.5045 0.031 Uiso 1 1 calc R . . C28 C 0.64551(16) 1.34866(12) 0.59457(12) 0.0223(3) Uani 1 1 d . . . H28 H 0.6204 1.4122 0.6191 0.027 Uiso 1 1 calc R . . C29 C 0.59087(15) 1.26893(12) 0.62640(11) 0.0182(3) Uani 1 1 d . . . C30 C 0.62764(15) 1.17523(12) 0.59064(11) 0.0192(3) Uani 1 1 d . . . C31 C 0.56696(15) 1.09036(11) 0.62299(11) 0.0186(3) Uani 1 1 d . . . C32 C 0.45479(15) 1.11085(11) 0.68620(11) 0.0174(3) Uani 1 1 d . . . H32 H 0.3748 1.0954 0.6402 0.021 Uiso 1 1 calc R . . C33 C 0.48733(14) 1.22673(11) 0.75316(11) 0.0164(3) Uani 1 1 d . . . C34 C 0.60822(14) 1.26505(11) 0.83066(11) 0.0177(3) Uani 1 1 d . . . H34 H 0.6920 1.2789 0.8003 0.021 Uiso 1 1 calc R . . C36 C 0.45646(15) 1.11174(12) 0.85633(11) 0.0200(3) Uani 1 1 d . . . H36 H 0.4462 1.0690 0.8974 0.024 Uiso 1 1 calc R . . C37 C 0.41796(15) 1.04227(11) 0.74579(11) 0.0192(3) Uani 1 1 d . . . H37 H 0.4668 0.9872 0.7257 0.023 Uiso 1 1 calc R . . C38 C 0.23398(18) 0.91819(13) 0.76248(13) 0.0286(4) Uani 1 1 d . . . H38A H 0.2405 0.9525 0.8346 0.043 Uiso 1 1 calc R . . H38B H 0.2883 0.8687 0.7445 0.043 Uiso 1 1 calc R . . H38C H 0.1417 0.8807 0.7362 0.043 Uiso 1 1 calc R . . C39 C 0.36732(15) 1.18428(12) 0.88325(11) 0.0185(3) Uani 1 1 d . . . C40 C 0.38374(14) 1.25599(11) 0.82416(11) 0.0169(3) Uani 1 1 d . . . C41 C 0.58851(15) 1.36899(12) 0.90793(11) 0.0193(3) Uani 1 1 d . . . C42 C 0.66312(16) 1.46376(12) 0.88828(12) 0.0226(3) Uani 1 1 d . . . H42A H 0.6319 1.5244 0.9274 0.034 Uiso 1 1 calc R . . H42B H 0.6474 1.4494 0.8179 0.034 Uiso 1 1 calc R . . H42C H 0.7579 1.4784 0.9069 0.034 Uiso 1 1 calc R . . C43 C 0.61997(16) 1.38800(13) 1.01580(12) 0.0243(3) Uani 1 1 d . . . H43A H 0.5606 1.3328 1.0311 0.036 Uiso 1 1 calc R . . H43B H 0.6078 1.4559 1.0582 0.036 Uiso 1 1 calc R . . H43C H 0.7118 1.3875 1.0274 0.036 Uiso 1 1 calc R . . C44 C 0.25274(15) 1.25415(12) 0.77750(11) 0.0192(3) Uani 1 1 d . . . H44A H 0.2706 1.2901 0.7313 0.023 Uiso 1 1 calc R . . H44B H 0.2033 1.1807 0.7386 0.023 Uiso 1 1 calc R . . C45 C 0.16815(15) 1.30545(12) 0.85212(12) 0.0210(3) Uani 1 1 d . . . H45 H 0.2122 1.3539 0.9149 0.025 Uiso 1 1 calc R . . C46 C 0.03834(16) 1.28991(12) 0.83915(12) 0.0213(3) Uani 1 1 d . . . C47 C -0.04737(18) 1.21558(16) 0.74584(14) 0.0356(4) Uani 1 1 d . . . H47A H 0.0074 1.1821 0.6970 0.053 Uiso 1 1 calc R . . H47B H -0.0929 1.2538 0.7197 0.053 Uiso 1 1 calc R . . H47C H -0.1128 1.1622 0.7596 0.053 Uiso 1 1 calc R . . C48 C -0.03288(17) 1.34829(13) 0.91990(13) 0.0256(3) Uani 1 1 d . . . H48A H 0.0297 1.3916 0.9792 0.038 Uiso 1 1 calc R . . H48B H -0.1027 1.2985 0.9349 0.038 Uiso 1 1 calc R . . H48C H -0.0723 1.3929 0.8984 0.038 Uiso 1 1 calc R . . O1 O 0.52539(12) 0.88665(10) 0.89202(9) 0.0316(3) Uani 1 1 d . . . O2 O 0.89534(10) 0.89038(8) 0.80585(8) 0.0213(2) Uani 1 1 d . . . O3 O 0.55617(11) 0.60925(9) 0.76370(9) 0.0253(3) Uani 1 1 d . . . O4 O 0.69704(13) 0.55719(9) 0.54982(9) 0.0299(3) Uani 1 1 d . . . O5 O 0.89991(11) 0.76166(9) 0.61093(8) 0.0232(2) Uani 1 1 d . . . O6 O 0.60096(12) 1.01017(9) 0.59919(9) 0.0267(3) Uani 1 1 d . . . O7 O 0.50085(10) 1.28766(8) 0.69357(8) 0.0179(2) Uani 1 1 d . . . O8 O 0.27973(11) 0.99475(8) 0.72201(8) 0.0215(2) Uani 1 1 d . . . O9 O 0.29397(11) 1.19072(9) 0.94687(8) 0.0248(3) Uani 1 1 d . . . O10 O 0.44753(10) 1.35986(8) 0.89112(8) 0.0188(2) Uani 1 1 d . . . 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 0.0278(8) 0.0259(8) 0.0193(7) 0.0118(6) 0.0041(6) 0.0107(7) C2 0.0362(9) 0.0219(8) 0.0196(8) 0.0079(6) 0.0005(7) 0.0094(7) C3 0.0303(9) 0.0233(8) 0.0233(8) 0.0113(7) -0.0038(7) 0.0017(7) C4 0.0217(8) 0.0278(8) 0.0244(8) 0.0140(7) 0.0008(6) 0.0044(6) C5 0.0236(8) 0.0219(7) 0.0178(7) 0.0096(6) 0.0017(6) 0.0077(6) C6 0.0225(8) 0.0228(7) 0.0184(7) 0.0103(6) 0.0019(6) 0.0078(6) C7 0.0225(8) 0.0258(8) 0.0189(7) 0.0093(6) 0.0033(6) 0.0083(6) C8 0.0184(7) 0.0226(7) 0.0183(7) 0.0083(6) 0.0030(6) 0.0056(6) C9 0.0173(7) 0.0202(7) 0.0191(7) 0.0079(6) 0.0022(6) 0.0052(6) C10 0.0227(8) 0.0200(7) 0.0192(7) 0.0080(6) 0.0015(6) 0.0072(6) C11 0.0242(8) 0.0226(8) 0.0249(8) 0.0097(7) -0.0020(6) 0.0072(6) C12 0.0241(8) 0.0199(7) 0.0226(8) 0.0075(6) 0.0000(6) 0.0039(6) C13 0.0195(8) 0.0211(7) 0.0244(8) 0.0084(6) 0.0025(6) 0.0055(6) C14 0.0284(9) 0.0260(8) 0.0308(9) 0.0096(7) 0.0053(7) -0.0001(7) C15 0.0302(9) 0.0201(7) 0.0203(8) 0.0112(6) 0.0063(6) 0.0079(6) C16 0.0238(8) 0.0234(8) 0.0205(8) 0.0114(6) 0.0074(6) 0.0094(6) C17 0.0290(9) 0.0240(8) 0.0224(8) 0.0128(7) 0.0059(6) 0.0107(7) C18 0.0424(11) 0.0323(9) 0.0230(9) 0.0134(7) 0.0044(7) 0.0127(8) C19 0.0327(9) 0.0277(8) 0.0323(9) 0.0170(7) 0.0092(7) 0.0082(7) C20 0.0286(9) 0.0307(9) 0.0274(9) 0.0157(7) 0.0076(7) 0.0150(7) C35 0.0185(7) 0.0228(7) 0.0224(8) 0.0096(6) 0.0002(6) 0.0072(6) C21 0.0272(9) 0.0326(9) 0.0271(9) 0.0147(7) 0.0075(7) 0.0111(7) C22 0.0295(9) 0.0323(9) 0.0350(10) 0.0131(8) 0.0071(7) 0.0128(7) C23 0.0818(18) 0.0751(17) 0.0554(14) 0.0462(14) 0.0326(13) 0.0562(15) C24 0.0304(10) 0.0345(10) 0.0411(11) 0.0110(8) 0.0030(8) 0.0144(8) C25 0.0228(8) 0.0223(8) 0.0220(8) 0.0055(6) 0.0054(6) 0.0058(6) C26 0.0251(8) 0.0288(8) 0.0228(8) 0.0085(7) 0.0100(6) 0.0048(7) C27 0.0270(9) 0.0248(8) 0.0264(8) 0.0129(7) 0.0075(7) 0.0015(7) C28 0.0238(8) 0.0200(7) 0.0234(8) 0.0089(6) 0.0049(6) 0.0056(6) C29 0.0163(7) 0.0202(7) 0.0164(7) 0.0064(6) 0.0015(5) 0.0031(6) C30 0.0178(7) 0.0191(7) 0.0184(7) 0.0060(6) 0.0015(6) 0.0027(6) C31 0.0187(7) 0.0179(7) 0.0175(7) 0.0052(6) 0.0012(6) 0.0046(6) C32 0.0174(7) 0.0165(7) 0.0183(7) 0.0069(6) 0.0015(5) 0.0042(6) C33 0.0150(7) 0.0170(7) 0.0182(7) 0.0081(6) 0.0021(5) 0.0043(5) C34 0.0140(7) 0.0197(7) 0.0190(7) 0.0065(6) 0.0011(5) 0.0051(6) C36 0.0206(8) 0.0206(7) 0.0209(8) 0.0104(6) 0.0012(6) 0.0053(6) C37 0.0194(7) 0.0177(7) 0.0215(8) 0.0088(6) 0.0033(6) 0.0051(6) C38 0.0288(9) 0.0271(8) 0.0303(9) 0.0161(7) 0.0046(7) 0.0003(7) C39 0.0163(7) 0.0196(7) 0.0163(7) 0.0056(6) -0.0010(5) 0.0015(6) C40 0.0157(7) 0.0172(7) 0.0166(7) 0.0053(6) 0.0015(5) 0.0044(5) C41 0.0138(7) 0.0211(7) 0.0210(7) 0.0060(6) 0.0015(6) 0.0051(6) C42 0.0179(7) 0.0196(7) 0.0269(8) 0.0060(6) 0.0016(6) 0.0043(6) C43 0.0209(8) 0.0278(8) 0.0209(8) 0.0056(7) 0.0006(6) 0.0069(6) C44 0.0163(7) 0.0223(7) 0.0186(7) 0.0068(6) 0.0015(6) 0.0060(6) C45 0.0194(7) 0.0210(7) 0.0203(7) 0.0054(6) 0.0012(6) 0.0060(6) C46 0.0201(8) 0.0204(7) 0.0249(8) 0.0094(6) 0.0030(6) 0.0070(6) C47 0.0199(8) 0.0410(10) 0.0343(10) 0.0008(8) -0.0007(7) 0.0104(8) C48 0.0217(8) 0.0295(8) 0.0283(9) 0.0117(7) 0.0054(6) 0.0109(7) O1 0.0203(6) 0.0332(7) 0.0337(7) 0.0042(6) 0.0073(5) 0.0079(5) O2 0.0169(5) 0.0244(6) 0.0210(6) 0.0072(5) 0.0025(4) 0.0055(4) O3 0.0236(6) 0.0233(6) 0.0298(6) 0.0139(5) 0.0036(5) 0.0022(5) O4 0.0382(7) 0.0211(6) 0.0294(6) 0.0081(5) 0.0072(5) 0.0089(5) O5 0.0270(6) 0.0250(6) 0.0238(6) 0.0135(5) 0.0099(5) 0.0112(5) O6 0.0308(6) 0.0223(6) 0.0305(6) 0.0108(5) 0.0101(5) 0.0123(5) O7 0.0185(5) 0.0187(5) 0.0197(5) 0.0097(4) 0.0051(4) 0.0067(4) O8 0.0197(5) 0.0200(5) 0.0242(6) 0.0105(5) 0.0028(4) 0.0010(4) O9 0.0228(6) 0.0310(6) 0.0226(6) 0.0128(5) 0.0067(5) 0.0068(5) O10 0.0138(5) 0.0184(5) 0.0214(5) 0.0045(4) 0.0014(4) 0.0049(4) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 C2 1.376(2) . ? C1 C6 1.402(2) . ? C1 H1 0.9500 . ? C2 C3 1.394(2) . ? C2 H2 0.9500 . ? C3 C4 1.374(2) . ? C3 H3 0.9500 . ? C4 C5 1.392(2) . ? C4 H4 0.9500 . ? C5 O2 1.3663(19) . ? C5 C6 1.400(2) . ? C6 C7 1.471(2) . ? C7 O1 1.214(2) . ? C7 C8 1.522(2) . ? C8 C13 1.531(2) . ? C8 C9 1.531(2) . ? C8 H8 1.0000 . ? C9 O2 1.4370(19) . ? C9 C16 1.531(2) . ? C9 C10 1.541(2) . ? C10 C11 1.537(2) . ? C10 C17 1.565(2) . ? C10 H10 1.0000 . ? C11 C12 1.547(2) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 C15 1.515(2) . ? C12 C13 1.540(2) . ? C12 H12 1.0000 . ? C13 O3 1.4251(18) . ? C13 H13 1.0000 . ? C14 O3 1.422(2) . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? C15 O4 1.208(2) . ? C15 C16 1.556(2) . ? C16 O5 1.4298(18) . ? C16 C20 1.520(2) . ? C17 O5 1.4659(18) . ? C17 C18 1.518(2) . ? C17 C19 1.521(2) . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? C20 C21 1.485(2) . ? C20 H20A 0.9900 . ? C20 H20B 0.9900 . ? C35 C34 1.541(2) . ? C35 C36 1.547(2) . ? C35 H35A 0.9900 . ? C35 H35B 0.9900 . ? C21 C22 1.334(2) . ? C21 H21 0.9500 . ? C22 C23 1.491(3) . ? C22 C24 1.492(2) . ? C23 H23A 0.9800 . ? C23 H23B 0.9800 . ? C23 H23C 0.9800 . ? C24 H24A 0.9800 . ? C24 H24B 0.9800 . ? C24 H24C 0.9800 . ? C25 C26 1.378(2) . ? C25 C30 1.401(2) . ? C25 H25 0.9500 . ? C26 C27 1.393(2) . ? C26 H26 0.9500 . ? C27 C28 1.383(2) . ? C27 H27 0.9500 . ? C28 C29 1.393(2) . ? C28 H28 0.9500 . ? C29 O7 1.3716(18) . ? C29 C30 1.400(2) . ? C30 C31 1.475(2) . ? C31 O6 1.2143(18) . ? C31 C32 1.523(2) . ? C32 C33 1.528(2) . ? C32 C37 1.5335(19) . ? C32 H32 1.0000 . ? C33 O7 1.4382(17) . ? C33 C40 1.537(2) . ? C33 C34 1.541(2) . ? C34 C41 1.562(2) . ? C34 H34 1.0000 . ? C36 C39 1.513(2) . ? C36 C37 1.540(2) . ? C36 H36 1.0000 . ? C37 O8 1.4216(19) . ? C37 H37 1.0000 . ? C38 O8 1.4244(18) . ? C38 H38A 0.9800 . ? C38 H38B 0.9800 . ? C38 H38C 0.9800 . ? C39 O9 1.2077(18) . ? C39 C40 1.559(2) . ? C40 O10 1.4265(18) . ? C40 C44 1.522(2) . ? C41 O10 1.4644(18) . ? C41 C43 1.523(2) . ? C41 C42 1.524(2) . ? C42 H42A 0.9800 . ? C42 H42B 0.9800 . ? C42 H42C 0.9800 . ? C43 H43A 0.9800 . ? C43 H43B 0.9800 . ? C43 H43C 0.9800 . ? C44 C45 1.505(2) . ? C44 H44A 0.9900 . ? C44 H44B 0.9900 . ? C45 C46 1.326(2) . ? C45 H45 0.9500 . ? C46 C47 1.496(2) . ? C46 C48 1.498(2) . ? C47 H47A 0.9800 . ? C47 H47B 0.9800 . ? C47 H47C 0.9800 . ? C48 H48A 0.9800 . ? C48 H48B 0.9800 . ? C48 H48C 0.9800 . ? 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 C2 C1 C6 120.77(15) . . ? C2 C1 H1 119.6 . . ? C6 C1 H1 119.6 . . ? C1 C2 C3 119.66(15) . . ? C1 C2 H2 120.2 . . ? C3 C2 H2 120.2 . . ? C4 C3 C2 120.89(16) . . ? C4 C3 H3 119.6 . . ? C2 C3 H3 119.6 . . ? C3 C4 C5 119.41(16) . . ? C3 C4 H4 120.3 . . ? C5 C4 H4 120.3 . . ? O2 C5 C4 116.49(14) . . ? O2 C5 C6 122.72(14) . . ? C4 C5 C6 120.79(15) . . ? C5 C6 C1 118.48(15) . . ? C5 C6 C7 120.33(14) . . ? C1 C6 C7 121.12(14) . . ? O1 C7 C6 123.15(15) . . ? O1 C7 C8 122.72(15) . . ? C6 C7 C8 114.11(13) . . ? C7 C8 C13 114.92(13) . . ? C7 C8 C9 108.97(12) . . ? C13 C8 C9 111.41(13) . . ? C7 C8 H8 107.1 . . ? C13 C8 H8 107.1 . . ? C9 C8 H8 107.1 . . ? O2 C9 C16 107.20(12) . . ? O2 C9 C8 110.56(12) . . ? C16 C9 C8 112.91(12) . . ? O2 C9 C10 111.36(12) . . ? C16 C9 C10 99.02(12) . . ? C8 C9 C10 115.08(12) . . ? C11 C10 C9 106.56(12) . . ? C11 C10 C17 115.57(13) . . ? C9 C10 C17 102.28(12) . . ? C11 C10 H10 110.7 . . ? C9 C10 H10 110.7 . . ? C17 C10 H10 110.7 . . ? C10 C11 C12 109.96(13) . . ? C10 C11 H11A 109.7 . . ? C12 C11 H11A 109.7 . . ? C10 C11 H11B 109.7 . . ? C12 C11 H11B 109.7 . . ? H11A C11 H11B 108.2 . . ? C15 C12 C13 105.97(13) . . ? C15 C12 C11 110.11(13) . . ? C13 C12 C11 106.32(13) . . ? C15 C12 H12 111.4 . . ? C13 C12 H12 111.4 . . ? C11 C12 H12 111.4 . . ? O3 C13 C8 107.26(12) . . ? O3 C13 C12 112.24(13) . . ? C8 C13 C12 108.75(12) . . ? O3 C13 H13 109.5 . . ? C8 C13 H13 109.5 . . ? C12 C13 H13 109.5 . . ? O3 C14 H14A 109.5 . . ? O3 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? O3 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? O4 C15 C12 124.36(16) . . ? O4 C15 C16 121.85(15) . . ? C12 C15 C16 113.77(13) . . ? O5 C16 C20 110.69(13) . . ? O5 C16 C9 103.46(12) . . ? C20 C16 C9 114.12(13) . . ? O5 C16 C15 107.72(12) . . ? C20 C16 C15 113.91(13) . . ? C9 C16 C15 106.23(12) . . ? O5 C17 C18 107.89(13) . . ? O5 C17 C19 107.25(13) . . ? C18 C17 C19 109.30(14) . . ? O5 C17 C10 104.96(11) . . ? C18 C17 C10 115.37(14) . . ? C19 C17 C10 111.62(13) . . ? C17 C18 H18A 109.5 . . ? C17 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C17 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C17 C19 H19A 109.5 . . ? C17 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C17 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C21 C20 C16 116.41(14) . . ? C21 C20 H20A 108.2 . . ? C16 C20 H20A 108.2 . . ? C21 C20 H20B 108.2 . . ? C16 C20 H20B 108.2 . . ? H20A C20 H20B 107.3 . . ? C34 C35 C36 110.48(12) . . ? C34 C35 H35A 109.6 . . ? C36 C35 H35A 109.6 . . ? C34 C35 H35B 109.6 . . ? C36 C35 H35B 109.6 . . ? H35A C35 H35B 108.1 . . ? C22 C21 C20 125.59(16) . . ? C22 C21 H21 117.2 . . ? C20 C21 H21 117.2 . . ? C21 C22 C23 123.05(17) . . ? C21 C22 C24 122.49(17) . . ? C23 C22 C24 114.40(16) . . ? C22 C23 H23A 109.5 . . ? C22 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C22 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? C22 C24 H24A 109.5 . . ? C22 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C22 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? C26 C25 C30 120.58(15) . . ? C26 C25 H25 119.7 . . ? C30 C25 H25 119.7 . . ? C25 C26 C27 119.63(15) . . ? C25 C26 H26 120.2 . . ? C27 C26 H26 120.2 . . ? C28 C27 C26 121.11(15) . . ? C28 C27 H27 119.4 . . ? C26 C27 H27 119.4 . . ? C27 C28 C29 119.05(15) . . ? C27 C28 H28 120.5 . . ? C29 C28 H28 120.5 . . ? O7 C29 C28 116.59(13) . . ? O7 C29 C30 122.71(13) . . ? C28 C29 C30 120.70(14) . . ? C29 C30 C25 118.93(14) . . ? C29 C30 C31 120.31(13) . . ? C25 C30 C31 120.75(14) . . ? O6 C31 C30 123.04(14) . . ? O6 C31 C32 123.00(13) . . ? C30 C31 C32 113.93(12) . . ? C31 C32 C33 109.42(12) . . ? C31 C32 C37 114.87(12) . . ? C33 C32 C37 111.23(12) . . ? C31 C32 H32 107.0 . . ? C33 C32 H32 107.0 . . ? C37 C32 H32 107.0 . . ? O7 C33 C32 109.51(12) . . ? O7 C33 C40 108.38(11) . . ? C32 C33 C40 114.13(12) . . ? O7 C33 C34 111.54(11) . . ? C32 C33 C34 114.49(12) . . ? C40 C33 C34 98.29(11) . . ? C33 C34 C35 106.12(12) . . ? C33 C34 C41 102.75(11) . . ? C35 C34 C41 115.92(12) . . ? C33 C34 H34 110.5 . . ? C35 C34 H34 110.5 . . ? C41 C34 H34 110.5 . . ? C39 C36 C37 106.32(12) . . ? C39 C36 C35 109.06(12) . . ? C37 C36 C35 107.10(12) . . ? C39 C36 H36 111.4 . . ? C37 C36 H36 111.4 . . ? C35 C36 H36 111.4 . . ? O8 C37 C32 106.41(12) . . ? O8 C37 C36 112.67(12) . . ? C32 C37 C36 108.61(12) . . ? O8 C37 H37 109.7 . . ? C32 C37 H37 109.7 . . ? C36 C37 H37 109.7 . . ? O8 C38 H38A 109.5 . . ? O8 C38 H38B 109.5 . . ? H38A C38 H38B 109.5 . . ? O8 C38 H38C 109.5 . . ? H38A C38 H38C 109.5 . . ? H38B C38 H38C 109.5 . . ? O9 C39 C36 124.50(14) . . ? O9 C39 C40 122.01(14) . . ? C36 C39 C40 113.42(12) . . ? O10 C40 C44 109.36(12) . . ? O10 C40 C33 103.61(11) . . ? C44 C40 C33 116.08(12) . . ? O10 C40 C39 107.58(11) . . ? C44 C40 C39 113.01(12) . . ? C33 C40 C39 106.52(11) . . ? O10 C41 C43 107.84(12) . . ? O10 C41 C42 106.60(12) . . ? C43 C41 C42 109.67(13) . . ? O10 C41 C34 104.52(11) . . ? C43 C41 C34 115.57(13) . . ? C42 C41 C34 112.06(12) . . ? C41 C42 H42A 109.5 . . ? C41 C42 H42B 109.5 . . ? H42A C42 H42B 109.5 . . ? C41 C42 H42C 109.5 . . ? H42A C42 H42C 109.5 . . ? H42B C42 H42C 109.5 . . ? C41 C43 H43A 109.5 . . ? C41 C43 H43B 109.5 . . ? H43A C43 H43B 109.5 . . ? C41 C43 H43C 109.5 . . ? H43A C43 H43C 109.5 . . ? H43B C43 H43C 109.5 . . ? C45 C44 C40 113.17(13) . . ? C45 C44 H44A 108.9 . . ? C40 C44 H44A 108.9 . . ? C45 C44 H44B 108.9 . . ? C40 C44 H44B 108.9 . . ? H44A C44 H44B 107.8 . . ? C46 C45 C44 126.64(15) . . ? C46 C45 H45 116.7 . . ? C44 C45 H45 116.7 . . ? C45 C46 C47 124.10(15) . . ? C45 C46 C48 120.80(15) . . ? C47 C46 C48 115.10(14) . . ? C46 C47 H47A 109.5 . . ? C46 C47 H47B 109.5 . . ? H47A C47 H47B 109.5 . . ? C46 C47 H47C 109.5 . . ? H47A C47 H47C 109.5 . . ? H47B C47 H47C 109.5 . . ? C46 C48 H48A 109.5 . . ? C46 C48 H48B 109.5 . . ? H48A C48 H48B 109.5 . . ? C46 C48 H48C 109.5 . . ? H48A C48 H48C 109.5 . . ? H48B C48 H48C 109.5 . . ? C5 O2 C9 115.93(12) . . ? C14 O3 C13 112.41(13) . . ? C16 O5 C17 108.23(11) . . ? C29 O7 C33 114.40(11) . . ? C37 O8 C38 112.69(12) . . ? C40 O10 C41 108.62(11) . . ? _diffrn_measured_fraction_theta_max 0.905 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.749 _refine_diff_density_min -0.301 _refine_diff_density_rms 0.055 data_theod37 _database_code_depnum_ccdc_archive 'CCDC 737621' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C23 H24 O4' _chemical_formula_weight 364.42 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)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 10.2829(5) _cell_length_b 13.7839(7) _cell_length_c 13.8591(8) _cell_angle_alpha 90.00 _cell_angle_beta 109.118(2) _cell_angle_gamma 90.00 _cell_volume 1856.02(17) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 7362 _cell_measurement_theta_min 3.38 _cell_measurement_theta_max 68.31 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.33 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.304 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 776 _exptl_absorpt_coefficient_mu 0.711 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.789 _exptl_absorpt_correction_T_max 0.914 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_reflns_number 10317 _diffrn_reflns_av_R_equivalents 0.0251 _diffrn_reflns_av_sigmaI/netI 0.0266 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 4.55 _diffrn_reflns_theta_max 68.30 _reflns_number_total 3330 _reflns_number_gt 3052 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _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^)+(0.0580P)^2^+0.6853P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0019(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3330 _refine_ls_number_parameters 249 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0414 _refine_ls_R_factor_gt 0.0380 _refine_ls_wR_factor_ref 0.1092 _refine_ls_wR_factor_gt 0.1066 _refine_ls_goodness_of_fit_ref 1.087 _refine_ls_restrained_S_all 1.087 _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 0.88338(9) 0.92628(6) 0.79884(8) 0.0204(2) Uani 1 1 d . . . O2 O 1.15445(9) 0.92992(7) 0.78656(7) 0.0180(2) Uani 1 1 d . . . O3 O 1.20451(10) 0.74400(7) 0.68648(8) 0.0248(2) Uani 1 1 d . . . O4 O 0.67890(11) 0.66638(8) 0.71106(10) 0.0352(3) Uani 1 1 d . . . C1 C 0.45924(14) 0.92099(12) 0.73075(11) 0.0259(3) Uani 1 1 d . . . H1 H 0.3621 0.9221 0.7148 0.031 Uiso 1 1 calc R . . C2 C 0.52496(14) 0.83636(11) 0.72267(11) 0.0239(3) Uani 1 1 d . . . H2 H 0.4726 0.7789 0.7005 0.029 Uiso 1 1 calc R . . C3 C 0.66892(14) 0.83345(10) 0.74681(11) 0.0200(3) Uani 1 1 d . . . C4 C 0.73940(15) 0.74236(10) 0.74226(12) 0.0232(3) Uani 1 1 d . . . C5 C 0.89161(14) 0.74725(10) 0.77966(11) 0.0203(3) Uani 1 1 d . . . C6 C 0.96771(13) 0.84202(9) 0.80568(10) 0.0172(3) Uani 1 1 d . . . C7 C 1.05732(13) 0.85674(9) 0.73690(10) 0.0160(3) Uani 1 1 d . . . C8 C 0.98547(13) 0.89009(10) 0.62749(10) 0.0186(3) Uani 1 1 d . . . H8A H 0.9493 0.9565 0.6290 0.022 Uiso 1 1 calc R . . H8B H 1.0542 0.8934 0.5916 0.022 Uiso 1 1 calc R . . C9 C 0.86935(14) 0.82583(10) 0.56788(10) 0.0202(3) Uani 1 1 d . . . H9 H 0.8911 0.7597 0.5612 0.024 Uiso 1 1 calc R . . C10 C 0.73842(15) 0.85214(11) 0.52330(11) 0.0233(3) Uani 1 1 d . . . C11 C 0.68423(16) 0.95333(12) 0.52230(12) 0.0316(4) Uani 1 1 d . . . H11A H 0.7603 0.9971 0.5571 0.047 Uiso 1 1 calc R . . H11B H 0.6158 0.9543 0.5576 0.047 Uiso 1 1 calc R . . H11C H 0.6413 0.9747 0.4515 0.047 Uiso 1 1 calc R . . C12 C 0.53626(15) 1.00558(11) 0.76266(11) 0.0242(3) Uani 1 1 d . . . H12 H 0.4909 1.0642 0.7688 0.029 Uiso 1 1 calc R . . C13 C 0.67767(14) 1.00508(10) 0.78544(10) 0.0204(3) Uani 1 1 d . . . H13 H 0.7291 1.0630 0.8064 0.024 Uiso 1 1 calc R . . C14 C 0.74397(13) 0.91881(10) 0.77733(10) 0.0179(3) Uani 1 1 d . . . C15 C 0.97060(15) 0.66908(10) 0.78668(11) 0.0220(3) Uani 1 1 d . . . H15 H 0.9338 0.6057 0.7703 0.026 Uiso 1 1 calc R . . C16 C 1.12234(14) 0.68938(10) 0.82260(11) 0.0219(3) Uani 1 1 d . . . H16 H 1.1784 0.6292 0.8273 0.026 Uiso 1 1 calc R . . C17 C 1.15336(15) 0.74105(10) 0.92718(11) 0.0237(3) Uani 1 1 d . . . H17A H 1.1163 0.7022 0.9723 0.028 Uiso 1 1 calc R . . H17B H 1.2541 0.7472 0.9605 0.028 Uiso 1 1 calc R . . C18 C 1.08660(14) 0.84256(10) 0.91096(10) 0.0192(3) Uani 1 1 d . . . H18 H 1.0499 0.8587 0.9675 0.023 Uiso 1 1 calc R . . C19 C 1.18247(14) 0.92497(10) 0.89703(10) 0.0195(3) Uani 1 1 d . . . C20 C 0.62954(16) 0.77952(13) 0.47002(13) 0.0345(4) Uani 1 1 d . . . H20A H 0.6724 0.7161 0.4696 0.052 Uiso 1 1 calc R . . H20B H 0.5830 0.8007 0.3996 0.052 Uiso 1 1 calc R . . H20C H 0.5623 0.7744 0.5061 0.052 Uiso 1 1 calc R . . C21 C 1.13804(13) 0.76020(10) 0.74253(10) 0.0183(3) Uani 1 1 d . . . C22 C 1.33689(15) 0.90787(12) 0.94579(12) 0.0276(3) Uani 1 1 d . . . H22A H 1.3872 0.9649 0.9348 0.041 Uiso 1 1 calc R . . H22B H 1.3640 0.8509 0.9146 0.041 Uiso 1 1 calc R . . H22C H 1.3585 0.8969 1.0192 0.041 Uiso 1 1 calc R . . C23 C 1.14623(15) 1.02300(10) 0.93247(11) 0.0239(3) Uani 1 1 d . . . H23A H 1.0471 1.0345 0.9019 0.036 Uiso 1 1 calc R . . H23B H 1.1970 1.0744 0.9113 0.036 Uiso 1 1 calc R . . H23C H 1.1713 1.0231 1.0071 0.036 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 0.0150(5) 0.0134(5) 0.0343(6) -0.0017(4) 0.0102(4) 0.0009(3) O2 0.0170(5) 0.0188(5) 0.0179(5) -0.0012(4) 0.0052(4) -0.0040(3) O3 0.0249(5) 0.0250(5) 0.0285(5) 0.0005(4) 0.0143(4) 0.0054(4) O4 0.0294(6) 0.0205(5) 0.0601(8) -0.0090(5) 0.0206(5) -0.0104(4) C1 0.0167(7) 0.0366(8) 0.0258(7) 0.0071(6) 0.0089(6) 0.0034(6) C2 0.0191(7) 0.0287(8) 0.0245(7) 0.0025(6) 0.0080(6) -0.0034(6) C3 0.0204(7) 0.0202(7) 0.0215(7) 0.0012(5) 0.0097(5) -0.0014(5) C4 0.0241(7) 0.0194(7) 0.0304(8) -0.0007(6) 0.0146(6) -0.0042(6) C5 0.0236(7) 0.0155(7) 0.0255(7) -0.0001(5) 0.0130(6) -0.0028(5) C6 0.0171(6) 0.0125(6) 0.0236(7) 0.0002(5) 0.0087(5) 0.0018(5) C7 0.0146(6) 0.0143(6) 0.0193(7) -0.0004(5) 0.0057(5) -0.0007(5) C8 0.0188(6) 0.0175(6) 0.0190(7) 0.0017(5) 0.0055(5) 0.0011(5) C9 0.0238(7) 0.0179(6) 0.0188(7) -0.0017(5) 0.0069(5) 0.0005(5) C10 0.0231(7) 0.0280(7) 0.0171(7) -0.0023(6) 0.0044(5) -0.0004(6) C11 0.0270(8) 0.0362(9) 0.0250(8) -0.0011(6) -0.0003(6) 0.0111(7) C12 0.0239(7) 0.0270(7) 0.0239(7) 0.0060(6) 0.0108(6) 0.0091(6) C13 0.0218(7) 0.0204(7) 0.0200(7) 0.0016(5) 0.0082(5) 0.0027(5) C14 0.0159(6) 0.0205(7) 0.0192(7) 0.0018(5) 0.0082(5) 0.0006(5) C15 0.0281(7) 0.0156(6) 0.0253(7) 0.0010(5) 0.0128(6) -0.0004(5) C16 0.0251(7) 0.0169(7) 0.0251(7) 0.0035(6) 0.0100(6) 0.0059(5) C17 0.0281(7) 0.0205(7) 0.0230(7) 0.0051(6) 0.0091(6) 0.0049(6) C18 0.0225(7) 0.0184(7) 0.0185(7) 0.0014(5) 0.0092(5) 0.0020(5) C19 0.0200(7) 0.0216(7) 0.0164(7) -0.0006(5) 0.0055(5) 0.0003(5) C20 0.0263(8) 0.0442(10) 0.0277(8) -0.0071(7) 0.0017(6) -0.0062(7) C21 0.0155(6) 0.0177(7) 0.0207(7) -0.0015(5) 0.0046(5) 0.0011(5) C22 0.0207(7) 0.0336(8) 0.0253(8) -0.0017(6) 0.0031(6) 0.0010(6) C23 0.0258(7) 0.0211(7) 0.0245(7) -0.0043(6) 0.0076(6) -0.0019(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 O1 C14 1.3691(16) . ? O1 C6 1.4339(15) . ? O2 C7 1.4278(15) . ? O2 C19 1.4638(16) . ? O3 C21 1.2118(17) . ? O4 C4 1.2225(18) . ? C1 C2 1.371(2) . ? C1 C12 1.397(2) . ? C2 C3 1.4073(19) . ? C3 C14 1.3947(19) . ? C3 C4 1.4615(19) . ? C4 C5 1.480(2) . ? C5 C15 1.334(2) . ? C5 C6 1.5046(18) . ? C6 C7 1.5408(18) . ? C6 C18 1.5669(19) . ? C7 C8 1.5240(18) . ? C7 C21 1.5567(17) . ? C8 C9 1.4990(18) . ? C9 C10 1.335(2) . ? C10 C11 1.500(2) . ? C10 C20 1.503(2) . ? C12 C13 1.383(2) . ? C13 C14 1.3934(19) . ? C15 C16 1.501(2) . ? C16 C21 1.5257(19) . ? C16 C17 1.551(2) . ? C17 C18 1.5423(18) . ? C18 C19 1.5570(19) . ? C19 C23 1.5250(19) . ? C19 C22 1.5266(19) . ? 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 C6 121.40(10) . . ? C7 O2 C19 109.77(9) . . ? C2 C1 C12 119.50(13) . . ? C1 C2 C3 120.87(13) . . ? C14 C3 C2 118.85(12) . . ? C14 C3 C4 120.33(12) . . ? C2 C3 C4 120.81(12) . . ? O4 C4 C3 123.31(13) . . ? O4 C4 C5 121.34(13) . . ? C3 C4 C5 115.35(12) . . ? C15 C5 C4 122.51(13) . . ? C15 C5 C6 115.31(12) . . ? C4 C5 C6 122.06(12) . . ? O1 C6 C5 115.56(11) . . ? O1 C6 C7 108.89(10) . . ? C5 C6 C7 109.60(11) . . ? O1 C6 C18 109.16(10) . . ? C5 C6 C18 114.41(11) . . ? C7 C6 C18 97.65(10) . . ? O2 C7 C8 107.52(10) . . ? O2 C7 C6 105.10(10) . . ? C8 C7 C6 117.52(11) . . ? O2 C7 C21 107.60(10) . . ? C8 C7 C21 112.62(11) . . ? C6 C7 C21 105.87(10) . . ? C9 C8 C7 114.15(11) . . ? C10 C9 C8 126.53(13) . . ? C9 C10 C11 124.91(13) . . ? C9 C10 C20 121.50(14) . . ? C11 C10 C20 113.58(13) . . ? C13 C12 C1 120.83(13) . . ? C12 C13 C14 119.43(13) . . ? O1 C14 C13 115.05(12) . . ? O1 C14 C3 124.43(12) . . ? C13 C14 C3 120.50(12) . . ? C5 C15 C16 114.57(12) . . ? C15 C16 C21 102.96(11) . . ? C15 C16 C17 105.59(11) . . ? C21 C16 C17 110.33(11) . . ? C18 C17 C16 109.56(11) . . ? C17 C18 C19 114.23(11) . . ? C17 C18 C6 107.80(11) . . ? C19 C18 C6 102.74(10) . . ? O2 C19 C23 108.08(11) . . ? O2 C19 C22 106.87(11) . . ? C23 C19 C22 108.82(11) . . ? O2 C19 C18 104.36(10) . . ? C23 C19 C18 112.03(11) . . ? C22 C19 C18 116.19(12) . . ? O3 C21 C16 124.37(12) . . ? O3 C21 C7 121.93(12) . . ? C16 C21 C7 113.68(11) . . ? _diffrn_measured_fraction_theta_max 0.977 _diffrn_reflns_theta_full 65.00 _diffrn_measured_fraction_theta_full 0.984 _refine_diff_density_max 0.314 _refine_diff_density_min -0.219 _refine_diff_density_rms 0.050 data_theod32 _database_code_depnum_ccdc_archive 'CCDC 737622' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H26 O5' _chemical_formula_weight 346.41 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 10.9193(4) _cell_length_b 12.8300(5) _cell_length_c 13.3814(5) _cell_angle_alpha 90.00 _cell_angle_beta 105.650(2) _cell_angle_gamma 90.00 _cell_volume 1805.16(12) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 6333 _cell_measurement_theta_min 4.66 _cell_measurement_theta_max 68.23 _exptl_crystal_description rod _exptl_crystal_colour colorless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.275 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 744 _exptl_absorpt_coefficient_mu 0.739 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8087 _exptl_absorpt_correction_T_max 0.9432 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_reflns_number 11208 _diffrn_reflns_av_R_equivalents 0.0345 _diffrn_reflns_av_sigmaI/netI 0.0315 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 4.66 _diffrn_reflns_theta_max 68.40 _reflns_number_total 3199 _reflns_number_gt 2718 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _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^)+(0.0462P)^2^+0.5678P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.00144(19) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3199 _refine_ls_number_parameters 233 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0422 _refine_ls_R_factor_gt 0.0343 _refine_ls_wR_factor_ref 0.0916 _refine_ls_wR_factor_gt 0.0864 _refine_ls_goodness_of_fit_ref 1.003 _refine_ls_restrained_S_all 1.003 _refine_ls_shift/su_max 0.002 _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 0.82804(9) 0.39196(7) 0.79992(7) 0.0225(2) Uani 1 1 d . . . O2 O 0.96880(8) 0.25013(7) 0.83496(7) 0.0180(2) Uani 1 1 d . . . O3 O 1.12041(8) 0.10678(7) 0.74979(7) 0.0189(2) Uani 1 1 d . . . O4 O 1.09519(9) 0.15903(8) 0.53030(7) 0.0254(2) Uani 1 1 d . . . O5 O 0.76575(10) 0.45611(8) 0.64111(8) 0.0273(2) Uani 1 1 d . . . C1 C 0.86785(13) 0.29893(11) 0.86433(10) 0.0210(3) Uani 1 1 d . . . C2 C 0.93728(12) 0.21085(10) 0.73148(10) 0.0160(3) Uani 1 1 d . . . C3 C 1.06100(12) 0.19783(10) 0.69757(10) 0.0165(3) Uani 1 1 d . . . C4 C 1.15764(12) 0.28558(10) 0.72196(10) 0.0186(3) Uani 1 1 d . . . H4A H 1.1774 0.3011 0.7971 0.022 Uiso 1 1 calc R . . H4B H 1.2371 0.2609 0.7075 0.022 Uiso 1 1 calc R . . C5 C 1.11765(12) 0.38490(11) 0.66310(10) 0.0193(3) Uani 1 1 d . . . H5 H 1.1015 0.3807 0.5898 0.023 Uiso 1 1 calc R . . C6 C 1.10207(12) 0.47824(11) 0.70145(11) 0.0207(3) Uani 1 1 d . . . C7 C 1.11788(14) 0.50154(12) 0.81396(11) 0.0264(3) Uani 1 1 d . . . H7A H 1.1305 0.4363 0.8535 0.040 Uiso 1 1 calc R . . H7B H 1.0415 0.5368 0.8221 0.040 Uiso 1 1 calc R . . H7C H 1.1920 0.5468 0.8398 0.040 Uiso 1 1 calc R . . C8 C 0.92350(15) 0.33902(12) 0.97288(11) 0.0290(3) Uani 1 1 d . . . H8A H 0.9964 0.3841 0.9742 0.043 Uiso 1 1 calc R . . H8B H 0.9515 0.2801 1.0201 0.043 Uiso 1 1 calc R . . H8C H 0.8589 0.3789 0.9950 0.043 Uiso 1 1 calc R . . C9 C 0.81026(12) 0.38366(11) 0.69645(11) 0.0199(3) Uani 1 1 d . . . C10 C 0.84964(12) 0.28437(10) 0.65835(10) 0.0175(3) Uani 1 1 d . . . C11 C 0.81936(12) 0.25831(11) 0.55836(10) 0.0193(3) Uani 1 1 d . . . H11 H 0.7671 0.3003 0.5052 0.023 Uiso 1 1 calc R . . C12 C 0.87534(12) 0.15674(11) 0.53731(10) 0.0202(3) Uani 1 1 d . . . H12 H 0.8501 0.1382 0.4619 0.024 Uiso 1 1 calc R . . C13 C 1.01879(13) 0.17102(10) 0.57996(10) 0.0185(3) Uani 1 1 d . . . C14 C 1.06717(15) 0.57164(11) 0.63161(12) 0.0291(3) Uani 1 1 d . . . H14A H 0.9803 0.5936 0.6288 0.044 Uiso 1 1 calc R . . H14B H 1.0721 0.5534 0.5617 0.044 Uiso 1 1 calc R . . H14C H 1.1263 0.6288 0.6589 0.044 Uiso 1 1 calc R . . C15 C 0.89568(12) 0.09430(10) 0.72145(10) 0.0167(3) Uani 1 1 d . . . H15 H 0.8344 0.0801 0.7635 0.020 Uiso 1 1 calc R . . C16 C 1.02335(12) 0.03662(10) 0.76838(10) 0.0182(3) Uani 1 1 d . . . C17 C 1.05043(13) 0.02229(12) 0.88506(11) 0.0241(3) Uani 1 1 d . . . H17A H 1.0410 0.0893 0.9174 0.036 Uiso 1 1 calc R . . H17B H 1.1374 -0.0035 0.9131 0.036 Uiso 1 1 calc R . . H17C H 0.9903 -0.0281 0.8999 0.036 Uiso 1 1 calc R . . C18 C 1.03773(14) -0.06750(11) 0.71874(12) 0.0267(3) Uani 1 1 d . . . H18A H 1.1204 -0.0981 0.7538 0.040 Uiso 1 1 calc R . . H18B H 1.0323 -0.0570 0.6451 0.040 Uiso 1 1 calc R . . H18C H 0.9697 -0.1146 0.7253 0.040 Uiso 1 1 calc R . . C19 C 0.83255(12) 0.07304(11) 0.60526(10) 0.0197(3) Uani 1 1 d . . . H19A H 0.7389 0.0749 0.5919 0.024 Uiso 1 1 calc R . . H19B H 0.8570 0.0029 0.5866 0.024 Uiso 1 1 calc R . . C20 C 0.75214(14) 0.23087(11) 0.85612(11) 0.0244(3) Uani 1 1 d . . . H20A H 0.7781 0.1661 0.8949 0.037 Uiso 1 1 calc R . . H20B H 0.7123 0.2145 0.7830 0.037 Uiso 1 1 calc R . . H20C H 0.6912 0.2680 0.8851 0.037 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 0.0277(5) 0.0193(5) 0.0221(5) -0.0019(4) 0.0097(4) 0.0036(4) O2 0.0187(5) 0.0213(5) 0.0144(5) -0.0041(4) 0.0051(3) 0.0018(4) O3 0.0158(5) 0.0183(5) 0.0232(5) 0.0037(4) 0.0062(4) 0.0014(4) O4 0.0244(5) 0.0325(6) 0.0229(5) -0.0042(4) 0.0124(4) -0.0015(4) O5 0.0287(5) 0.0233(5) 0.0308(6) 0.0050(4) 0.0095(4) 0.0084(4) C1 0.0252(7) 0.0207(7) 0.0188(7) -0.0004(5) 0.0089(5) 0.0056(6) C2 0.0162(6) 0.0191(7) 0.0130(6) -0.0025(5) 0.0045(5) -0.0001(5) C3 0.0159(6) 0.0170(7) 0.0169(7) 0.0005(5) 0.0047(5) 0.0023(5) C4 0.0157(6) 0.0200(7) 0.0191(7) 0.0002(5) 0.0032(5) -0.0016(5) C5 0.0170(6) 0.0225(7) 0.0170(6) 0.0009(5) 0.0022(5) -0.0028(5) C6 0.0160(6) 0.0219(7) 0.0226(7) 0.0006(6) 0.0022(5) -0.0025(6) C7 0.0278(8) 0.0264(8) 0.0255(8) -0.0053(6) 0.0081(6) -0.0043(6) C8 0.0361(8) 0.0305(8) 0.0219(8) -0.0061(6) 0.0106(6) 0.0034(7) C9 0.0166(6) 0.0211(7) 0.0226(7) 0.0007(6) 0.0066(5) 0.0013(5) C10 0.0141(6) 0.0188(7) 0.0203(7) 0.0011(5) 0.0061(5) -0.0004(5) C11 0.0156(6) 0.0241(7) 0.0178(7) 0.0027(5) 0.0039(5) 0.0000(5) C12 0.0190(7) 0.0256(8) 0.0150(6) -0.0029(5) 0.0031(5) -0.0001(6) C13 0.0207(7) 0.0167(7) 0.0189(7) 0.0001(5) 0.0068(5) 0.0010(5) C14 0.0290(8) 0.0217(8) 0.0316(8) 0.0009(6) -0.0003(6) -0.0018(6) C15 0.0166(6) 0.0174(7) 0.0169(6) -0.0019(5) 0.0060(5) -0.0004(5) C16 0.0164(6) 0.0177(7) 0.0213(7) -0.0004(5) 0.0063(5) -0.0021(5) C17 0.0234(7) 0.0266(8) 0.0223(7) 0.0035(6) 0.0058(5) -0.0009(6) C18 0.0225(7) 0.0214(8) 0.0338(8) -0.0058(6) 0.0035(6) 0.0033(6) C19 0.0175(7) 0.0207(7) 0.0198(7) -0.0037(5) 0.0031(5) -0.0009(5) C20 0.0258(7) 0.0258(8) 0.0259(8) -0.0008(6) 0.0143(6) 0.0030(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 O1 C9 1.3495(17) . ? O1 C1 1.4678(16) . ? O2 C1 1.4126(15) . ? O2 C2 1.4257(15) . ? O3 C3 1.4245(15) . ? O3 C16 1.4621(15) . ? O4 C13 1.2085(15) . ? O5 C9 1.2061(17) . ? C1 C8 1.5059(19) . ? C1 C20 1.515(2) . ? C2 C10 1.5027(18) . ? C2 C3 1.5458(17) . ? C2 C15 1.5580(18) . ? C3 C4 1.5170(18) . ? C3 C13 1.5543(17) . ? C4 C5 1.4998(18) . ? C5 C6 1.332(2) . ? C6 C7 1.4985(19) . ? C6 C14 1.5041(19) . ? C9 C10 1.4784(18) . ? C10 C11 1.3315(19) . ? C11 C12 1.4980(19) . ? C12 C13 1.5266(18) . ? C12 C19 1.5580(18) . ? C15 C19 1.5454(17) . ? C15 C16 1.5535(18) . ? C16 C18 1.5187(18) . ? C16 C17 1.5198(19) . ? 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 C9 O1 C1 118.43(10) . . ? C1 O2 C2 115.15(10) . . ? C3 O3 C16 109.47(9) . . ? O2 C1 O1 109.07(10) . . ? O2 C1 C8 106.12(11) . . ? O1 C1 C8 105.50(11) . . ? O2 C1 C20 114.99(11) . . ? O1 C1 C20 108.48(11) . . ? C8 C1 C20 112.24(12) . . ? O2 C2 C10 110.79(10) . . ? O2 C2 C3 108.80(10) . . ? C10 C2 C3 109.28(10) . . ? O2 C2 C15 114.29(10) . . ? C10 C2 C15 115.26(11) . . ? C3 C2 C15 97.39(10) . . ? O3 C3 C4 107.74(10) . . ? O3 C3 C2 105.24(10) . . ? C4 C3 C2 117.97(11) . . ? O3 C3 C13 106.65(10) . . ? C4 C3 C13 112.41(10) . . ? C2 C3 C13 106.09(10) . . ? C5 C4 C3 115.49(11) . . ? C6 C5 C4 127.67(13) . . ? C5 C6 C7 125.06(13) . . ? C5 C6 C14 120.94(13) . . ? C7 C6 C14 113.99(12) . . ? O5 C9 O1 119.46(13) . . ? O5 C9 C10 123.98(13) . . ? O1 C9 C10 116.56(12) . . ? C11 C10 C9 123.13(13) . . ? C11 C10 C2 116.01(12) . . ? C9 C10 C2 120.65(12) . . ? C10 C11 C12 113.84(12) . . ? C11 C12 C13 104.77(11) . . ? C11 C12 C19 106.74(11) . . ? C13 C12 C19 107.67(10) . . ? O4 C13 C12 124.75(12) . . ? O4 C13 C3 121.66(12) . . ? C12 C13 C3 113.53(10) . . ? C19 C15 C16 115.52(10) . . ? C19 C15 C2 107.25(10) . . ? C16 C15 C2 102.32(10) . . ? O3 C16 C18 107.57(11) . . ? O3 C16 C17 107.48(10) . . ? C18 C16 C17 109.18(12) . . ? O3 C16 C15 104.51(10) . . ? C18 C16 C15 115.44(11) . . ? C17 C16 C15 112.19(11) . . ? C15 C19 C12 110.05(11) . . ? _diffrn_measured_fraction_theta_max 0.966 _diffrn_reflns_theta_full 60.00 _diffrn_measured_fraction_theta_full 0.982 _refine_diff_density_max 0.267 _refine_diff_density_min -0.173 _refine_diff_density_rms 0.037 data_theod35 _database_code_depnum_ccdc_archive 'CCDC 737623' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H26 O5' _chemical_formula_weight 346.41 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 8.0045(2) _cell_length_b 13.2751(4) _cell_length_c 16.4708(5) _cell_angle_alpha 90.00 _cell_angle_beta 92.4170(10) _cell_angle_gamma 90.00 _cell_volume 1748.64(9) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 9946 _cell_measurement_theta_min 3.33 _cell_measurement_theta_max 68.16 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.33 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.27 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.316 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 744 _exptl_absorpt_coefficient_mu 0.763 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.791 _exptl_absorpt_correction_T_max 0.919 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_reflns_number 13879 _diffrn_reflns_av_R_equivalents 0.0209 _diffrn_reflns_av_sigmaI/netI 0.0144 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 4.28 _diffrn_reflns_theta_max 68.15 _reflns_number_total 3087 _reflns_number_gt 3004 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _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^)+(0.0282P)^2^+0.9146P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0044(2) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3087 _refine_ls_number_parameters 233 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0322 _refine_ls_R_factor_gt 0.0315 _refine_ls_wR_factor_ref 0.0744 _refine_ls_wR_factor_gt 0.0739 _refine_ls_goodness_of_fit_ref 1.043 _refine_ls_restrained_S_all 1.043 _refine_ls_shift/su_max 0.002 _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 1.27011(11) 0.42467(6) -0.03099(5) 0.0211(2) Uani 1 1 d . . . O2 O 1.15203(10) 0.57579(6) -0.03231(5) 0.01713(19) Uani 1 1 d . . . O3 O 1.10517(9) 0.67070(6) 0.08594(5) 0.01532(19) Uani 1 1 d . . . O4 O 1.35035(10) 0.59241(6) 0.33077(5) 0.01598(19) Uani 1 1 d . . . O5 O 1.37053(10) 0.72997(6) 0.19299(5) 0.0195(2) Uani 1 1 d . . . C1 C 1.22977(14) 0.49788(9) 0.00679(7) 0.0157(2) Uani 1 1 d . . . C2 C 1.25054(13) 0.50884(8) 0.09584(7) 0.0146(2) Uani 1 1 d . . . C3 C 1.18357(14) 0.59978(8) 0.13873(7) 0.0139(2) Uani 1 1 d . . . C4 C 1.32828(14) 0.64272(8) 0.19250(7) 0.0140(2) Uani 1 1 d . . . C5 C 1.40336(14) 0.56321(8) 0.25230(7) 0.0142(2) Uani 1 1 d . . . C6 C 1.59408(14) 0.56093(9) 0.25406(7) 0.0168(2) Uani 1 1 d . . . H6A H 1.6321 0.5379 0.2007 0.020 Uiso 1 1 calc R . . H6B H 1.6382 0.6297 0.2640 0.020 Uiso 1 1 calc R . . C7 C 1.66119(14) 0.49132(9) 0.31967(7) 0.0175(3) Uani 1 1 d . . . H7 H 1.6645 0.5171 0.3735 0.021 Uiso 1 1 calc R . . C8 C 1.71640(14) 0.39760(9) 0.31060(7) 0.0170(2) Uani 1 1 d . . . C9 C 1.76710(16) 0.33284(10) 0.38238(8) 0.0237(3) Uani 1 1 d . . . H9A H 1.7585 0.3719 0.4325 0.036 Uiso 1 1 calc R . . H9B H 1.8828 0.3102 0.3774 0.036 Uiso 1 1 calc R . . H9C H 1.6931 0.2741 0.3841 0.036 Uiso 1 1 calc R . . C10 C 1.16477(15) 0.67537(9) 0.00654(7) 0.0164(2) Uani 1 1 d . . . C11 C 1.04332(16) 0.74199(9) -0.04100(8) 0.0209(3) Uani 1 1 d . . . H11A H 1.0475 0.8102 -0.0183 0.031 Uiso 1 1 calc R . . H11B H 0.9299 0.7150 -0.0375 0.031 Uiso 1 1 calc R . . H11C H 1.0736 0.7440 -0.0980 0.031 Uiso 1 1 calc R . . C12 C 1.05231(14) 0.56026(9) 0.19772(7) 0.0147(2) Uani 1 1 d . . . H12A H 0.9968 0.6179 0.2236 0.018 Uiso 1 1 calc R . . H12B H 0.9658 0.5208 0.1670 0.018 Uiso 1 1 calc R . . C13 C 1.13827(14) 0.49322(8) 0.26378(7) 0.0147(2) Uani 1 1 d . . . H13 H 1.0690 0.4322 0.2740 0.018 Uiso 1 1 calc R . . C14 C 1.31395(14) 0.46224(8) 0.23417(7) 0.0143(2) Uani 1 1 d . . . H14 H 1.3639 0.4064 0.2679 0.017 Uiso 1 1 calc R . . C15 C 1.31339(14) 0.43777(8) 0.14565(7) 0.0149(2) Uani 1 1 d . . . H15 H 1.3550 0.3757 0.1261 0.018 Uiso 1 1 calc R . . C16 C 1.18870(14) 0.54656(9) 0.34482(7) 0.0157(2) Uani 1 1 d . . . C17 C 1.21365(16) 0.46999(9) 0.41327(8) 0.0221(3) Uani 1 1 d . . . H17A H 1.2763 0.5012 0.4590 0.033 Uiso 1 1 calc R . . H17B H 1.2762 0.4120 0.3937 0.033 Uiso 1 1 calc R . . H17C H 1.1045 0.4475 0.4310 0.033 Uiso 1 1 calc R . . C18 C 1.07399(15) 0.63043(9) 0.37141(7) 0.0203(3) Uani 1 1 d . . . H18A H 1.0741 0.6852 0.3315 0.030 Uiso 1 1 calc R . . H18B H 1.1138 0.6559 0.4246 0.030 Uiso 1 1 calc R . . H18C H 0.9601 0.6042 0.3752 0.030 Uiso 1 1 calc R . . C19 C 1.73116(15) 0.34616(9) 0.23004(7) 0.0206(3) Uani 1 1 d . . . H19A H 1.7045 0.3941 0.1862 0.031 Uiso 1 1 calc R . . H19B H 1.6530 0.2894 0.2262 0.031 Uiso 1 1 calc R . . H19C H 1.8456 0.3214 0.2252 0.031 Uiso 1 1 calc R . . C20 C 1.34527(15) 0.70899(9) 0.00280(7) 0.0191(3) Uani 1 1 d . . . H20A H 1.4181 0.6599 0.0313 0.029 Uiso 1 1 calc R . . H20B H 1.3588 0.7751 0.0288 0.029 Uiso 1 1 calc R . . H20C H 1.3757 0.7137 -0.0541 0.029 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 0.0243(4) 0.0207(4) 0.0183(5) -0.0054(3) 0.0000(3) 0.0026(3) O2 0.0213(4) 0.0161(4) 0.0138(4) -0.0010(3) -0.0021(3) -0.0003(3) O3 0.0169(4) 0.0170(4) 0.0120(4) 0.0020(3) 0.0003(3) 0.0033(3) O4 0.0158(4) 0.0183(4) 0.0138(4) -0.0033(3) 0.0000(3) -0.0014(3) O5 0.0228(4) 0.0142(4) 0.0213(5) -0.0001(3) -0.0023(3) -0.0025(3) C1 0.0140(5) 0.0165(6) 0.0165(6) -0.0006(4) 0.0000(4) -0.0019(4) C2 0.0125(5) 0.0150(6) 0.0163(6) -0.0024(4) 0.0005(4) -0.0020(4) C3 0.0151(5) 0.0134(5) 0.0130(6) 0.0009(4) -0.0008(4) 0.0014(4) C4 0.0144(5) 0.0148(6) 0.0129(6) -0.0018(4) 0.0024(4) 0.0007(4) C5 0.0152(6) 0.0139(5) 0.0134(6) -0.0017(4) -0.0007(4) 0.0001(4) C6 0.0141(6) 0.0165(6) 0.0197(6) -0.0012(4) -0.0008(4) -0.0006(4) C7 0.0135(5) 0.0236(6) 0.0152(6) -0.0033(5) -0.0025(4) 0.0002(5) C8 0.0125(5) 0.0214(6) 0.0168(6) 0.0002(5) -0.0013(4) -0.0010(4) C9 0.0225(6) 0.0279(7) 0.0204(7) 0.0025(5) -0.0013(5) 0.0063(5) C10 0.0209(6) 0.0153(6) 0.0131(6) -0.0009(4) 0.0014(4) -0.0003(4) C11 0.0261(6) 0.0214(6) 0.0151(6) 0.0021(5) -0.0008(5) 0.0031(5) C12 0.0131(5) 0.0169(6) 0.0142(6) 0.0000(4) -0.0004(4) -0.0002(4) C13 0.0151(5) 0.0145(5) 0.0146(6) 0.0003(4) 0.0005(4) -0.0010(4) C14 0.0146(5) 0.0131(5) 0.0151(6) 0.0001(4) -0.0014(4) -0.0005(4) C15 0.0139(5) 0.0134(5) 0.0174(6) -0.0032(4) 0.0003(4) -0.0010(4) C16 0.0157(5) 0.0164(6) 0.0151(6) 0.0001(4) 0.0001(4) -0.0012(4) C17 0.0295(7) 0.0202(6) 0.0164(6) 0.0017(5) 0.0001(5) 0.0001(5) C18 0.0206(6) 0.0229(6) 0.0174(6) -0.0034(5) 0.0004(5) 0.0030(5) C19 0.0233(6) 0.0184(6) 0.0198(7) -0.0019(5) -0.0017(5) 0.0009(5) C20 0.0221(6) 0.0177(6) 0.0178(6) -0.0004(5) 0.0032(5) -0.0024(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 1.2054(14) . ? O2 C1 1.3557(14) . ? O2 C10 1.4704(13) . ? O3 C3 1.4106(13) . ? O3 C10 1.4122(14) . ? O4 C5 1.4307(14) . ? O4 C16 1.4572(13) . ? O5 C4 1.2066(14) . ? C1 C2 1.4763(16) . ? C2 C15 1.3347(16) . ? C2 C3 1.5086(15) . ? C3 C4 1.5377(15) . ? C3 C12 1.5522(15) . ? C4 C5 1.5477(15) . ? C5 C6 1.5260(15) . ? C5 C14 1.5427(15) . ? C6 C7 1.5037(16) . ? C7 C8 1.3308(17) . ? C8 C19 1.5014(17) . ? C8 C9 1.5037(17) . ? C10 C11 1.5087(16) . ? C10 C20 1.5159(16) . ? C12 C13 1.5448(15) . ? C13 C16 1.5495(16) . ? C13 C14 1.5627(15) . ? C14 C15 1.4936(16) . ? C16 C18 1.5193(16) . ? C16 C17 1.5249(16) . ? 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 O2 C10 117.21(9) . . ? C3 O3 C10 116.18(8) . . ? C5 O4 C16 109.24(8) . . ? O1 C1 O2 119.83(11) . . ? O1 C1 C2 124.82(11) . . ? O2 C1 C2 115.28(10) . . ? C15 C2 C1 124.39(10) . . ? C15 C2 C3 114.21(10) . . ? C1 C2 C3 121.11(10) . . ? O3 C3 C2 113.77(9) . . ? O3 C3 C4 114.35(9) . . ? C2 C3 C4 107.00(9) . . ? O3 C3 C12 108.43(9) . . ? C2 C3 C12 106.61(9) . . ? C4 C3 C12 106.14(9) . . ? O5 C4 C3 124.32(10) . . ? O5 C4 C5 123.31(10) . . ? C3 C4 C5 112.13(9) . . ? O4 C5 C6 108.84(9) . . ? O4 C5 C14 104.91(9) . . ? C6 C5 C14 116.23(9) . . ? O4 C5 C4 105.55(9) . . ? C6 C5 C4 112.76(9) . . ? C14 C5 C4 107.74(9) . . ? C7 C6 C5 110.64(9) . . ? C8 C7 C6 127.17(11) . . ? C7 C8 C19 124.28(11) . . ? C7 C8 C9 121.75(11) . . ? C19 C8 C9 113.97(10) . . ? O3 C10 O2 110.09(9) . . ? O3 C10 C11 105.72(9) . . ? O2 C10 C11 105.65(9) . . ? O3 C10 C20 114.23(9) . . ? O2 C10 C20 107.20(9) . . ? C11 C10 C20 113.62(10) . . ? C13 C12 C3 110.03(9) . . ? C12 C13 C16 115.82(9) . . ? C12 C13 C14 108.16(9) . . ? C16 C13 C14 100.60(9) . . ? C15 C14 C5 111.11(9) . . ? C15 C14 C13 113.34(9) . . ? C5 C14 C13 97.31(9) . . ? C2 C15 C14 115.58(10) . . ? O4 C16 C18 106.93(9) . . ? O4 C16 C17 107.84(9) . . ? C18 C16 C17 109.72(10) . . ? O4 C16 C13 104.76(9) . . ? C18 C16 C13 116.39(9) . . ? C17 C16 C13 110.70(9) . . ? _diffrn_measured_fraction_theta_max 0.966 _diffrn_reflns_theta_full 60.00 _diffrn_measured_fraction_theta_full 0.973 _refine_diff_density_max 0.293 _refine_diff_density_min -0.185 _refine_diff_density_rms 0.035 data_theod31 _database_code_depnum_ccdc_archive 'CCDC 737624' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C19 H24 O4' _chemical_formula_weight 316.38 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 Orthorhombic _symmetry_space_group_name_H-M Pbca loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x+1/2, -y, z+1/2' '-x, -y, -z' '-x-1/2, y-1/2, z' 'x, -y-1/2, z-1/2' 'x-1/2, y, -z-1/2' _cell_length_a 7.6777(4) _cell_length_b 12.8146(8) _cell_length_c 33.0175(18) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3248.5(3) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 5283 _cell_measurement_theta_min 6.36 _cell_measurement_theta_max 68.24 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.42 _exptl_crystal_size_mid 0.38 _exptl_crystal_size_min 0.08 _exptl_crystal_density_diffrn 1.294 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1360 _exptl_absorpt_coefficient_mu 0.724 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7508 _exptl_absorpt_correction_T_max 0.9444 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_reflns_number 14719 _diffrn_reflns_av_R_equivalents 0.0579 _diffrn_reflns_av_sigmaI/netI 0.0347 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -39 _diffrn_reflns_limit_l_max 39 _diffrn_reflns_theta_min 6.36 _diffrn_reflns_theta_max 68.23 _reflns_number_total 2918 _reflns_number_gt 2268 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _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^)+(0.0510P)^2^+1.3421P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.00068(13) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2918 _refine_ls_number_parameters 213 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0593 _refine_ls_R_factor_gt 0.0396 _refine_ls_wR_factor_ref 0.1051 _refine_ls_wR_factor_gt 0.0951 _refine_ls_goodness_of_fit_ref 1.014 _refine_ls_restrained_S_all 1.014 _refine_ls_shift/su_max 0.002 _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 1.06461(18) 1.30401(10) 0.58265(4) 0.0309(3) Uani 1 1 d . . . O2 O 1.08724(15) 0.99537(9) 0.60796(3) 0.0198(3) Uani 1 1 d . . . O3 O 0.84876(16) 0.91765(9) 0.66802(4) 0.0231(3) Uani 1 1 d . . . O4 O 0.59175(16) 1.08505(11) 0.68788(4) 0.0308(3) Uani 1 1 d . . . C1 C 1.0860(2) 1.21364(14) 0.59275(5) 0.0210(4) Uani 1 1 d . . . C2 C 1.0097(2) 1.17091(13) 0.63053(5) 0.0187(4) Uani 1 1 d . . . C3 C 1.0132(2) 1.05506(13) 0.63982(5) 0.0172(4) Uani 1 1 d . . . C4 C 0.8278(2) 1.01564(14) 0.64747(5) 0.0194(4) Uani 1 1 d . . . C5 C 0.7137(2) 0.99891(14) 0.61049(5) 0.0218(4) Uani 1 1 d . . . H5A H 0.7723 0.9495 0.5919 0.026 Uiso 1 1 calc R . . H5B H 0.6023 0.9669 0.6191 0.026 Uiso 1 1 calc R . . C6 C 0.6759(2) 1.09865(14) 0.58809(5) 0.0212(4) Uani 1 1 d . . . H6 H 0.6315 1.1545 0.6039 0.025 Uiso 1 1 calc R . . C7 C 0.6972(2) 1.11813(15) 0.54884(6) 0.0258(4) Uani 1 1 d . . . C8 C 0.6537(3) 1.22388(17) 0.53160(6) 0.0346(5) Uani 1 1 d . . . H8A H 0.6000 1.2671 0.5527 0.052 Uiso 1 1 calc R . . H8B H 0.5723 1.2157 0.5090 0.052 Uiso 1 1 calc R . . H8C H 0.7605 1.2576 0.5220 0.052 Uiso 1 1 calc R . . C9 C 1.1940(2) 1.13866(14) 0.56825(5) 0.0243(4) Uani 1 1 d . . . H9A H 1.3012 1.1743 0.5589 0.029 Uiso 1 1 calc R . . H9B H 1.1275 1.1168 0.5440 0.029 Uiso 1 1 calc R . . C10 C 1.2434(2) 1.04287(14) 0.59279(5) 0.0224(4) Uani 1 1 d . . . H10A H 1.3075 0.9927 0.5755 0.027 Uiso 1 1 calc R . . H10B H 1.3198 1.0632 0.6156 0.027 Uiso 1 1 calc R . . C11 C 0.9326(2) 1.23021(14) 0.65851(5) 0.0228(4) Uani 1 1 d . . . H11 H 0.9179 1.3034 0.6555 0.027 Uiso 1 1 calc R . . C12 C 0.8707(2) 1.17161(14) 0.69522(5) 0.0238(4) Uani 1 1 d . . . H12 H 0.8156 1.2184 0.7158 0.029 Uiso 1 1 calc R . . C13 C 1.0342(2) 1.11416(14) 0.71199(5) 0.0233(4) Uani 1 1 d . . . H13A H 1.1303 1.1647 0.7158 0.028 Uiso 1 1 calc R . . H13B H 1.0067 1.0829 0.7387 0.028 Uiso 1 1 calc R . . C14 C 1.0915(2) 1.02807(13) 0.68236(5) 0.0191(4) Uani 1 1 d . . . H14 H 1.2215 1.0241 0.6809 0.023 Uiso 1 1 calc R . . C15 C 1.0126(2) 0.91868(14) 0.69082(5) 0.0210(4) Uani 1 1 d . . . C16 C 0.7438(2) 1.09125(14) 0.67837(5) 0.0222(4) Uani 1 1 d . . . C17 C 0.7621(3) 1.04031(19) 0.51844(6) 0.0401(5) Uani 1 1 d . . . H17A H 0.6643 1.0150 0.5021 0.060 Uiso 1 1 calc R . . H17B H 0.8162 0.9814 0.5326 0.060 Uiso 1 1 calc R . . H17C H 0.8483 1.0736 0.5008 0.060 Uiso 1 1 calc R . . C18 C 1.1277(2) 0.83197(15) 0.67446(6) 0.0281(4) Uani 1 1 d . . . H18A H 1.1531 0.8451 0.6458 0.042 Uiso 1 1 calc R . . H18B H 1.0674 0.7649 0.6772 0.042 Uiso 1 1 calc R . . H18C H 1.2369 0.8300 0.6898 0.042 Uiso 1 1 calc R . . C19 C 0.9671(2) 0.89630(15) 0.73489(5) 0.0265(4) Uani 1 1 d . . . H19A H 0.9246 0.8245 0.7374 0.040 Uiso 1 1 calc R . . H19B H 0.8764 0.9448 0.7439 0.040 Uiso 1 1 calc R . . H19C H 1.0712 0.9052 0.7517 0.040 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 0.0404(8) 0.0193(7) 0.0329(7) 0.0071(6) 0.0040(6) -0.0010(6) O2 0.0184(6) 0.0182(6) 0.0228(6) -0.0011(5) 0.0023(5) 0.0011(5) O3 0.0185(6) 0.0203(6) 0.0304(6) 0.0095(5) -0.0066(5) -0.0039(5) O4 0.0206(7) 0.0435(8) 0.0282(7) 0.0083(6) 0.0062(5) 0.0044(6) C1 0.0187(9) 0.0205(9) 0.0240(8) 0.0027(7) -0.0032(7) -0.0039(8) C2 0.0158(8) 0.0179(9) 0.0226(8) 0.0009(7) -0.0030(7) -0.0012(7) C3 0.0165(8) 0.0168(8) 0.0183(8) 0.0002(6) -0.0003(6) 0.0013(7) C4 0.0188(9) 0.0175(9) 0.0218(8) 0.0048(7) -0.0009(7) 0.0004(7) C5 0.0171(8) 0.0221(9) 0.0261(9) 0.0028(7) -0.0035(7) -0.0022(8) C6 0.0155(8) 0.0215(9) 0.0265(9) 0.0027(7) -0.0023(7) -0.0009(7) C7 0.0166(8) 0.0337(11) 0.0271(9) 0.0039(8) -0.0029(7) -0.0027(8) C8 0.0271(10) 0.0434(12) 0.0333(10) 0.0175(9) -0.0037(8) -0.0057(10) C9 0.0204(9) 0.0273(10) 0.0252(9) 0.0056(7) 0.0045(7) 0.0005(8) C10 0.0164(8) 0.0261(10) 0.0247(8) 0.0024(7) 0.0036(7) 0.0023(7) C11 0.0250(10) 0.0184(9) 0.0250(9) 0.0005(7) -0.0018(7) -0.0003(8) C12 0.0268(10) 0.0228(10) 0.0219(8) -0.0023(7) 0.0030(7) 0.0034(8) C13 0.0259(10) 0.0243(9) 0.0197(8) 0.0002(7) -0.0008(7) -0.0015(8) C14 0.0169(9) 0.0194(9) 0.0211(8) 0.0037(7) -0.0009(7) -0.0010(7) C15 0.0158(8) 0.0212(9) 0.0259(8) 0.0060(7) -0.0044(7) -0.0017(7) C16 0.0209(9) 0.0265(10) 0.0191(8) 0.0080(7) 0.0011(7) 0.0044(8) C17 0.0372(12) 0.0568(15) 0.0262(10) -0.0034(9) -0.0008(9) 0.0021(11) C18 0.0258(10) 0.0213(10) 0.0373(10) 0.0056(8) -0.0042(8) 0.0017(8) C19 0.0209(9) 0.0286(10) 0.0300(9) 0.0100(8) -0.0036(8) -0.0050(8) _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 1.216(2) . ? O2 C3 1.4194(19) . ? O2 C10 1.435(2) . ? O3 C4 1.436(2) . ? O3 C15 1.466(2) . ? O4 C16 1.212(2) . ? C1 C2 1.483(2) . ? C1 C9 1.505(2) . ? C2 C11 1.335(2) . ? C2 C3 1.516(2) . ? C3 C4 1.531(2) . ? C3 C14 1.566(2) . ? C4 C5 1.518(2) . ? C4 C16 1.548(2) . ? C5 C6 1.505(2) . ? C6 C7 1.330(2) . ? C7 C17 1.500(3) . ? C7 C8 1.507(3) . ? C9 C10 1.519(2) . ? C11 C12 1.503(2) . ? C12 C16 1.523(3) . ? C12 C13 1.557(2) . ? C13 C14 1.539(2) . ? C14 C15 1.553(2) . ? C15 C18 1.519(3) . ? C15 C19 1.524(2) . ? 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 C3 O2 C10 111.39(13) . . ? C4 O3 C15 109.31(13) . . ? O1 C1 C2 121.93(16) . . ? O1 C1 C9 122.34(16) . . ? C2 C1 C9 115.72(15) . . ? C11 C2 C1 123.18(16) . . ? C11 C2 C3 115.16(15) . . ? C1 C2 C3 121.66(15) . . ? O2 C3 C2 112.62(13) . . ? O2 C3 C4 108.46(13) . . ? C2 C3 C4 109.88(14) . . ? O2 C3 C14 113.07(13) . . ? C2 C3 C14 113.85(13) . . ? C4 C3 C14 97.82(13) . . ? O3 C4 C5 108.73(14) . . ? O3 C4 C3 105.22(13) . . ? C5 C4 C3 116.78(14) . . ? O3 C4 C16 106.42(13) . . ? C5 C4 C16 112.18(14) . . ? C3 C4 C16 106.84(14) . . ? C6 C5 C4 112.74(15) . . ? C7 C6 C5 127.95(17) . . ? C6 C7 C17 124.61(18) . . ? C6 C7 C8 120.64(18) . . ? C17 C7 C8 114.75(17) . . ? C1 C9 C10 111.51(14) . . ? O2 C10 C9 108.70(14) . . ? C2 C11 C12 114.44(16) . . ? C11 C12 C16 104.21(14) . . ? C11 C12 C13 105.59(15) . . ? C16 C12 C13 109.03(14) . . ? C14 C13 C12 110.09(14) . . ? C13 C14 C15 114.90(14) . . ? C13 C14 C3 107.57(13) . . ? C15 C14 C3 102.16(13) . . ? O3 C15 C18 108.08(14) . . ? O3 C15 C19 107.00(14) . . ? C18 C15 C19 109.57(15) . . ? O3 C15 C14 104.53(13) . . ? C18 C15 C14 111.66(14) . . ? C19 C15 C14 115.54(15) . . ? O4 C16 C12 124.49(17) . . ? O4 C16 C4 122.11(17) . . ? C12 C16 C4 113.40(14) . . ? _diffrn_measured_fraction_theta_max 0.982 _diffrn_reflns_theta_full 55.00 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 0.303 _refine_diff_density_min -0.164 _refine_diff_density_rms 0.041 data_theod36 _database_code_depnum_ccdc_archive 'CCDC 737625' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C23 H22 O6' _chemical_formula_weight 394.41 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 Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.8298(5) _cell_length_b 9.8418(4) _cell_length_c 20.5815(9) _cell_angle_alpha 89.130(3) _cell_angle_beta 89.002(4) _cell_angle_gamma 67.618(3) _cell_volume 1840.76(14) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 5725 _cell_measurement_theta_min 4.30 _cell_measurement_theta_max 64.19 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.12 _exptl_crystal_density_diffrn 1.423 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 832 _exptl_absorpt_coefficient_mu 0.849 _exptl_absorpt_correction_type multi-scans _exptl_absorpt_correction_T_min 0.8158 _exptl_absorpt_correction_T_max 0.9050 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_reflns_number 13913 _diffrn_reflns_av_R_equivalents 0.0559 _diffrn_reflns_av_sigmaI/netI 0.0563 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 4.30 _diffrn_reflns_theta_max 65.15 _reflns_number_total 4995 _reflns_number_gt 4135 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.1085P)^2^+0.0139P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_number_reflns 4995 _refine_ls_number_parameters 530 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0783 _refine_ls_R_factor_gt 0.0640 _refine_ls_wR_factor_ref 0.1654 _refine_ls_wR_factor_gt 0.1547 _refine_ls_goodness_of_fit_ref 1.083 _refine_ls_restrained_S_all 1.083 _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 C1 C 0.3534(5) 0.8679(5) -0.0073(2) 0.0187(10) Uani 1 1 d . . . C2 C 0.2923(5) 0.9443(5) -0.0641(2) 0.0242(12) Uani 1 1 d . . . H2 H 0.1888 0.9861 -0.0697 0.029 Uiso 1 1 calc R . . C3 C 0.3872(6) 0.9574(5) -0.1119(2) 0.0255(12) Uani 1 1 d . . . H3 H 0.3473 1.0090 -0.1509 0.031 Uiso 1 1 calc R . . C4 C 0.5390(6) 0.8975(5) -0.1049(2) 0.0276(12) Uani 1 1 d . . . H4 H 0.6018 0.9087 -0.1383 0.033 Uiso 1 1 calc R . . C5 C 0.5967(5) 0.8220(5) -0.0488(2) 0.0228(11) Uani 1 1 d . . . H5 H 0.7004 0.7801 -0.0436 0.027 Uiso 1 1 calc R . . C6 C 0.5053(5) 0.8058(5) 0.0007(2) 0.0208(11) Uani 1 1 d . . . C7 C 0.5660(5) 0.7397(5) 0.0627(2) 0.0231(11) Uani 1 1 d . . . C8 C 0.4547(5) 0.7413(5) 0.1149(2) 0.0176(10) Uani 1 1 d . . . C9 C 0.4986(5) 0.6494(5) 0.1723(2) 0.0204(11) Uani 1 1 d . . . H9 H 0.6042 0.5816 0.1755 0.024 Uiso 1 1 calc R . . C10 C 0.3835(5) 0.5907(5) 0.1934(2) 0.0241(11) Uani 1 1 d . . . H10 H 0.4158 0.5244 0.2322 0.029 Uiso 1 1 calc R . . C11 C 0.3675(5) 0.5067(5) 0.1335(2) 0.0209(11) Uani 1 1 d . . . H11C H 0.3120 0.4445 0.1457 0.025 Uiso 1 1 calc R . . H11D H 0.4661 0.4419 0.1175 0.025 Uiso 1 1 calc R . . C12 C 0.2853(5) 0.6168(5) 0.0792(2) 0.0203(11) Uani 1 1 d . . . H12 H 0.3263 0.5789 0.0353 0.024 Uiso 1 1 calc R . . C13 C 0.3000(5) 0.7649(5) 0.0927(2) 0.0184(10) Uani 1 1 d . . . C14 C 0.1820(5) 0.8223(5) 0.1471(2) 0.0180(10) Uani 1 1 d . . . C15 C 0.2426(5) 0.7227(5) 0.2077(3) 0.0225(12) Uani 1 1 d . . . C16 C 0.1144(5) 0.6613(5) 0.0818(2) 0.0219(11) Uani 1 1 d . . . C17 C 0.0605(6) 0.5508(6) 0.1134(2) 0.0275(12) Uani 1 1 d . . . H17D H 0.0893 0.5373 0.1591 0.041 Uiso 1 1 calc R . . H17E H 0.1044 0.4566 0.0909 0.041 Uiso 1 1 calc R . . H17F H -0.0469 0.5868 0.1107 0.041 Uiso 1 1 calc R . . C18 C 0.0459(6) 0.7042(6) 0.0154(2) 0.0285(12) Uani 1 1 d . . . H18D H -0.0616 0.7452 0.0200 0.043 Uiso 1 1 calc R . . H18E H 0.0764 0.6172 -0.0123 0.043 Uiso 1 1 calc R . . H18F H 0.0784 0.7780 -0.0045 0.043 Uiso 1 1 calc R . . C19 C 0.1275(5) 0.9851(5) 0.1631(2) 0.0206(11) Uani 1 1 d . . . H19C H 0.2013 1.0030 0.1901 0.025 Uiso 1 1 calc R . . H19D H 0.1168 1.0426 0.1223 0.025 Uiso 1 1 calc R . . C20 C -0.0179(5) 1.0368(5) 0.1990(2) 0.0226(11) Uani 1 1 d . . . H20 H -0.0382 0.9655 0.2247 0.027 Uiso 1 1 calc R . . C21 C -0.1207(5) 1.1720(5) 0.1985(2) 0.0200(11) Uani 1 1 d . . . C22 C -0.2561(6) 1.1970(5) 0.2366(2) 0.0247(12) Uani 1 1 d . . . H22 H -0.2557 1.1215 0.2660 0.030 Uiso 1 1 calc R . . C23 C -0.1094(7) 1.3011(6) 0.1619(3) 0.0379(14) Uani 1 1 d . . . H23D H -0.0060 1.2806 0.1511 0.057 Uiso 1 1 calc R . . H23E H -0.1487 1.3888 0.1891 0.057 Uiso 1 1 calc R . . H23F H -0.1661 1.3177 0.1219 0.057 Uiso 1 1 calc R . . C1' C 0.6268(5) 0.6449(5) 0.5065(2) 0.0183(10) Uani 1 1 d . . . C2' C 0.5618(5) 0.7015(6) 0.5667(2) 0.0253(12) Uani 1 1 d . . . H2' H 0.5206 0.8045 0.5740 0.030 Uiso 1 1 calc R . . C3' C 0.5594(5) 0.6040(6) 0.6148(2) 0.0252(12) Uani 1 1 d . . . H3' H 0.5140 0.6412 0.6554 0.030 Uiso 1 1 calc R . . C4' C 0.6206(6) 0.4539(6) 0.6062(2) 0.0281(12) Uani 1 1 d . . . H4' H 0.6179 0.3888 0.6403 0.034 Uiso 1 1 calc R . . C5' C 0.6860(5) 0.4000(5) 0.5470(2) 0.0234(11) Uani 1 1 d . . . H5' H 0.7296 0.2968 0.5408 0.028 Uiso 1 1 calc R . . C6' C 0.6893(5) 0.4948(5) 0.4960(2) 0.0206(11) Uani 1 1 d . . . C7' C 0.7450(5) 0.4366(5) 0.4309(2) 0.0235(11) Uani 1 1 d . . . C8' C 0.7456(5) 0.5486(5) 0.3820(2) 0.0184(10) Uani 1 1 d . . . C9' C 0.8436(5) 0.5063(5) 0.3246(2) 0.0225(11) Uani 1 1 d . . . H9' H 0.9101 0.4006 0.3204 0.027 Uiso 1 1 calc R . . C10' C 0.9043(5) 0.6196(5) 0.3061(2) 0.0234(11) Uani 1 1 d . . . H10' H 0.9731 0.5887 0.2679 0.028 Uiso 1 1 calc R . . C11' C 0.9842(5) 0.6331(5) 0.3687(2) 0.0237(11) Uani 1 1 d . . . H11A H 1.0460 0.5338 0.3849 0.028 Uiso 1 1 calc R . . H11B H 1.0492 0.6867 0.3586 0.028 Uiso 1 1 calc R . . C12' C 0.8717(5) 0.7154(5) 0.4215(2) 0.0189(10) Uani 1 1 d . . . H12' H 0.9064 0.6731 0.4655 0.023 Uiso 1 1 calc R . . C13' C 0.7231(5) 0.7016(5) 0.4056(2) 0.0171(10) Uani 1 1 d . . . C14' C 0.6704(5) 0.8214(5) 0.3531(2) 0.0202(11) Uani 1 1 d . . . C15' C 0.7773(5) 0.7633(5) 0.2936(2) 0.0199(11) Uani 1 1 d . . . C16' C 0.8286(5) 0.8858(5) 0.4210(2) 0.0214(11) Uani 1 1 d . . . C17' C 0.9408(5) 0.9380(6) 0.3907(2) 0.0259(12) Uani 1 1 d . . . H17A H 0.9560 0.9091 0.3449 0.039 Uiso 1 1 calc R . . H17B H 1.0340 0.8936 0.4138 0.039 Uiso 1 1 calc R . . H17C H 0.9055 1.0452 0.3936 0.039 Uiso 1 1 calc R . . C18' C 0.7848(6) 0.9512(6) 0.4882(2) 0.0287(12) Uani 1 1 d . . . H18A H 0.7464 1.0586 0.4849 0.043 Uiso 1 1 calc R . . H18B H 0.8711 0.9170 0.5162 0.043 Uiso 1 1 calc R . . H18C H 0.7088 0.9200 0.5067 0.043 Uiso 1 1 calc R . . C19' C 0.5087(5) 0.8749(5) 0.3360(2) 0.0223(11) Uani 1 1 d . . . H19A H 0.4927 0.8006 0.3087 0.027 Uiso 1 1 calc R . . H19B H 0.4499 0.8846 0.3765 0.027 Uiso 1 1 calc R . . C20' C 0.4556(5) 1.0192(5) 0.3006(2) 0.0214(11) Uani 1 1 d . . . H20' H 0.5264 1.0419 0.2756 0.026 Uiso 1 1 calc R . . C21' C 0.3183(5) 1.1187(5) 0.3009(2) 0.0235(11) Uani 1 1 d . . . C22' C 0.2932(5) 1.2527(6) 0.2635(3) 0.0279(13) Uani 1 1 d . . . H22' H 0.3764 1.2629 0.2433 0.034 Uiso 1 1 calc R . . C23' C 0.1892(6) 1.1066(7) 0.3357(3) 0.0402(15) Uani 1 1 d . . . H23A H 0.1143 1.1104 0.3041 0.060 Uiso 1 1 calc R . . H23B H 0.1479 1.1882 0.3661 0.060 Uiso 1 1 calc R . . H23C H 0.2204 1.0132 0.3597 0.060 Uiso 1 1 calc R . . O1 O 0.2526(3) 0.8645(3) 0.03952(15) 0.0192(7) Uani 1 1 d . . . O2 O 0.6972(3) 0.6857(4) 0.07404(16) 0.0330(9) Uani 1 1 d . . . O3 O 0.4653(4) 0.8034(3) 0.17655(15) 0.0227(8) Uani 1 1 d . . . O4 O 0.1823(4) 0.7502(4) 0.25961(17) 0.0313(9) Uani 1 1 d . . . O5 O 0.0609(3) 0.7933(3) 0.12226(15) 0.0211(8) Uani 1 1 d . . . O6 O -0.3676(4) 1.3056(4) 0.23340(19) 0.0393(10) Uani 1 1 d . . . O1' O 0.6194(3) 0.7465(3) 0.45947(15) 0.0191(7) Uani 1 1 d . . . O2' O 0.7902(4) 0.3071(4) 0.41661(17) 0.0344(9) Uani 1 1 d . . . O3' O 0.6867(3) 0.5436(4) 0.31855(15) 0.0248(8) Uani 1 1 d . . . O4' O 0.7617(4) 0.8352(4) 0.24471(17) 0.0297(9) Uani 1 1 d . . . O5' O 0.6966(3) 0.9418(3) 0.38074(15) 0.0199(7) Uani 1 1 d . . . O6' O 0.1758(4) 1.3515(4) 0.25613(19) 0.0422(10) Uani 1 1 d . . . 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 0.019(2) 0.020(2) 0.020(3) 0.000(2) -0.001(2) -0.010(2) C2 0.026(3) 0.025(3) 0.026(3) 0.003(2) -0.008(2) -0.014(2) C3 0.040(3) 0.022(3) 0.020(3) -0.001(2) -0.003(2) -0.017(2) C4 0.042(3) 0.027(3) 0.019(3) -0.008(2) 0.005(2) -0.019(2) C5 0.023(3) 0.023(3) 0.025(3) -0.010(2) -0.001(2) -0.012(2) C6 0.020(3) 0.023(3) 0.021(3) 0.000(2) 0.001(2) -0.009(2) C7 0.019(3) 0.020(2) 0.031(3) -0.001(2) -0.003(2) -0.007(2) C8 0.014(2) 0.017(2) 0.020(3) -0.0038(19) -0.0020(19) -0.0046(19) C9 0.021(2) 0.021(3) 0.017(3) -0.001(2) -0.006(2) -0.005(2) C10 0.021(3) 0.028(3) 0.024(3) 0.004(2) -0.005(2) -0.009(2) C11 0.018(2) 0.020(2) 0.023(3) 0.001(2) -0.003(2) -0.006(2) C12 0.023(3) 0.022(2) 0.018(3) 0.001(2) -0.002(2) -0.011(2) C13 0.018(2) 0.025(3) 0.013(3) 0.0033(19) -0.0054(19) -0.008(2) C14 0.016(2) 0.017(2) 0.021(3) -0.0016(19) -0.0035(19) -0.0062(19) C15 0.023(3) 0.017(2) 0.030(3) 0.001(2) -0.002(2) -0.010(2) C16 0.019(2) 0.025(3) 0.021(3) -0.006(2) -0.004(2) -0.007(2) C17 0.026(3) 0.027(3) 0.033(3) -0.001(2) -0.004(2) -0.015(2) C18 0.028(3) 0.036(3) 0.025(3) -0.006(2) -0.002(2) -0.016(2) C19 0.015(2) 0.016(2) 0.029(3) 0.004(2) -0.001(2) -0.0039(19) C20 0.019(3) 0.021(3) 0.027(3) 0.000(2) 0.003(2) -0.007(2) C21 0.015(2) 0.024(3) 0.019(3) 0.000(2) 0.0004(19) -0.007(2) C22 0.026(3) 0.021(3) 0.025(3) 0.002(2) -0.005(2) -0.006(2) C23 0.048(4) 0.024(3) 0.034(4) 0.002(2) 0.018(3) -0.006(3) C1' 0.017(2) 0.026(3) 0.015(3) 0.004(2) -0.0037(19) -0.012(2) C2' 0.028(3) 0.032(3) 0.019(3) 0.003(2) -0.001(2) -0.015(2) C3' 0.017(2) 0.038(3) 0.021(3) 0.000(2) -0.004(2) -0.011(2) C4' 0.035(3) 0.032(3) 0.027(3) 0.011(2) -0.012(2) -0.024(2) C5' 0.024(3) 0.014(2) 0.031(3) 0.006(2) -0.010(2) -0.006(2) C6' 0.016(2) 0.027(3) 0.024(3) 0.002(2) -0.005(2) -0.013(2) C7' 0.022(2) 0.020(3) 0.030(3) -0.003(2) -0.001(2) -0.009(2) C8' 0.020(2) 0.017(2) 0.019(3) 0.0012(19) -0.0054(19) -0.0069(19) C9' 0.023(3) 0.023(3) 0.021(3) -0.005(2) -0.002(2) -0.007(2) C10' 0.020(3) 0.026(3) 0.023(3) -0.001(2) 0.003(2) -0.006(2) C11' 0.018(2) 0.026(3) 0.026(3) 0.005(2) -0.002(2) -0.008(2) C12' 0.020(2) 0.020(2) 0.016(3) 0.0028(19) -0.0061(19) -0.0065(19) C13' 0.018(2) 0.011(2) 0.019(3) -0.0015(19) 0.0029(19) -0.0031(19) C14' 0.023(2) 0.019(3) 0.019(3) -0.001(2) -0.002(2) -0.009(2) C15' 0.019(2) 0.017(3) 0.027(3) 0.003(2) -0.005(2) -0.011(2) C16' 0.024(2) 0.020(2) 0.022(3) -0.002(2) -0.007(2) -0.010(2) C17' 0.021(3) 0.028(3) 0.029(3) 0.005(2) -0.004(2) -0.010(2) C18' 0.032(3) 0.022(3) 0.032(3) -0.008(2) -0.004(2) -0.008(2) C19' 0.027(3) 0.029(3) 0.015(3) -0.001(2) -0.0003(19) -0.016(2) C20' 0.021(3) 0.028(3) 0.020(3) 0.001(2) -0.005(2) -0.014(2) C21' 0.033(3) 0.018(3) 0.021(3) -0.002(2) 0.000(2) -0.010(2) C22' 0.017(3) 0.022(3) 0.039(4) -0.003(2) -0.008(2) -0.002(2) C23' 0.023(3) 0.052(4) 0.040(4) 0.022(3) -0.002(2) -0.008(3) O1 0.0146(16) 0.0224(17) 0.021(2) 0.0046(13) -0.0030(13) -0.0076(13) O2 0.0130(18) 0.045(2) 0.037(2) 0.0047(17) -0.0029(15) -0.0069(16) O3 0.0258(18) 0.0217(18) 0.0201(19) -0.0038(14) -0.0035(14) -0.0082(14) O4 0.035(2) 0.035(2) 0.021(2) 0.0024(16) 0.0044(17) -0.0112(17) O5 0.0155(16) 0.0229(17) 0.027(2) -0.0033(14) -0.0033(14) -0.0093(14) O6 0.026(2) 0.036(2) 0.048(3) -0.0026(18) 0.0064(17) -0.0031(18) O1' 0.0215(16) 0.0189(17) 0.0165(19) 0.0009(13) 0.0024(13) -0.0073(14) O2' 0.040(2) 0.020(2) 0.041(2) -0.0020(16) 0.0041(17) -0.0092(17) O3' 0.0251(18) 0.0246(19) 0.025(2) -0.0071(15) -0.0001(15) -0.0101(15) O4' 0.034(2) 0.029(2) 0.028(2) 0.0069(16) -0.0059(16) -0.0127(17) O5' 0.0212(16) 0.0162(16) 0.0235(19) -0.0010(13) -0.0053(14) -0.0082(13) O6' 0.035(2) 0.037(2) 0.046(3) 0.0064(18) -0.0011(18) -0.004(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 C1 O1 1.379(5) . ? C1 C6 1.394(7) . ? C1 C2 1.395(7) . ? C2 C3 1.382(7) . ? C3 C4 1.389(7) . ? C4 C5 1.372(7) . ? C5 C6 1.393(7) . ? C6 C7 1.454(7) . ? C7 O2 1.218(6) . ? C7 C8 1.516(7) . ? C8 O3 1.439(5) . ? C8 C9 1.445(6) . ? C8 C13 1.525(6) . ? C9 O3 1.427(5) . ? C9 C10 1.509(7) . ? C10 C15 1.523(7) . ? C10 C11 1.538(6) . ? C11 C12 1.552(6) . ? C12 C13 1.548(6) . ? C12 C16 1.567(6) . ? C13 O1 1.419(5) . ? C13 C14 1.546(6) . ? C14 O5 1.430(5) . ? C14 C19 1.523(6) . ? C14 C15 1.555(7) . ? C15 O4 1.196(6) . ? C16 O5 1.468(6) . ? C16 C17 1.514(7) . ? C16 C18 1.515(7) . ? C19 C20 1.506(7) . ? C20 C21 1.330(7) . ? C21 C22 1.472(7) . ? C21 C23 1.505(7) . ? C22 O6 1.207(6) . ? C1' O1' 1.364(5) . ? C1' C6' 1.385(7) . ? C1' C2' 1.406(7) . ? C2' C3' 1.374(7) . ? C3' C4' 1.379(7) . ? C4' C5' 1.383(7) . ? C5' C6' 1.401(7) . ? C6' C7' 1.477(7) . ? C7' O2' 1.218(6) . ? C7' C8' 1.484(7) . ? C8' O3' 1.446(5) . ? C8' C9' 1.470(7) . ? C8' C13' 1.523(6) . ? C9' O3' 1.450(5) . ? C9' C10' 1.494(7) . ? C10' C15' 1.510(7) . ? C10' C11' 1.555(6) . ? C11' C12' 1.537(6) . ? C12' C13' 1.558(6) . ? C12' C16' 1.566(6) . ? C13' O1' 1.448(5) . ? C13' C14' 1.531(6) . ? C14' O5' 1.434(5) . ? C14' C19' 1.517(6) . ? C14' C15' 1.565(7) . ? C15' O4' 1.199(6) . ? C16' O5' 1.467(5) . ? C16' C17' 1.506(7) . ? C16' C18' 1.519(6) . ? C19' C20' 1.496(7) . ? C20' C21' 1.332(7) . ? C21' C22' 1.456(7) . ? C21' C23' 1.489(7) . ? C22' O6' 1.203(6) . ? 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 C6 124.0(4) . . ? O1 C1 C2 114.9(4) . . ? C6 C1 C2 121.0(4) . . ? C3 C2 C1 117.9(5) . . ? C2 C3 C4 122.2(5) . . ? C5 C4 C3 118.9(5) . . ? C4 C5 C6 120.9(5) . . ? C5 C6 C1 119.1(4) . . ? C5 C6 C7 120.6(4) . . ? C1 C6 C7 120.0(4) . . ? O2 C7 C6 124.0(5) . . ? O2 C7 C8 120.2(4) . . ? C6 C7 C8 115.8(4) . . ? O3 C8 C9 59.3(3) . . ? O3 C8 C7 117.0(3) . . ? C9 C8 C7 121.1(4) . . ? O3 C8 C13 116.4(4) . . ? C9 C8 C13 113.3(4) . . ? C7 C8 C13 117.1(4) . . ? O3 C9 C8 60.1(3) . . ? O3 C9 C10 119.0(4) . . ? C8 C9 C10 111.6(4) . . ? C9 C10 C15 107.2(4) . . ? C9 C10 C11 103.4(4) . . ? C15 C10 C11 111.5(4) . . ? C10 C11 C12 110.0(4) . . ? C13 C12 C11 107.8(3) . . ? C13 C12 C16 102.0(4) . . ? C11 C12 C16 113.5(4) . . ? O1 C13 C8 113.2(4) . . ? O1 C13 C14 107.0(4) . . ? C8 C13 C14 113.3(3) . . ? O1 C13 C12 112.1(3) . . ? C8 C13 C12 111.3(4) . . ? C14 C13 C12 99.1(4) . . ? O5 C14 C19 108.0(3) . . ? O5 C14 C13 103.0(3) . . ? C19 C14 C13 117.5(4) . . ? O5 C14 C15 108.8(4) . . ? C19 C14 C15 112.3(4) . . ? C13 C14 C15 106.8(4) . . ? O4 C15 C10 125.0(5) . . ? O4 C15 C14 122.0(4) . . ? C10 C15 C14 113.0(4) . . ? O5 C16 C17 107.0(4) . . ? O5 C16 C18 107.6(4) . . ? C17 C16 C18 109.6(4) . . ? O5 C16 C12 104.1(3) . . ? C17 C16 C12 116.0(4) . . ? C18 C16 C12 112.0(4) . . ? C20 C19 C14 111.9(4) . . ? C21 C20 C19 126.6(5) . . ? C20 C21 C22 117.3(5) . . ? C20 C21 C23 125.1(5) . . ? C22 C21 C23 117.6(4) . . ? O6 C22 C21 125.2(5) . . ? O1' C1' C6' 123.0(4) . . ? O1' C1' C2' 115.8(4) . . ? C6' C1' C2' 121.2(4) . . ? C3' C2' C1' 118.2(5) . . ? C2' C3' C4' 122.3(5) . . ? C3' C4' C5' 118.7(5) . . ? C4' C5' C6' 121.2(4) . . ? C1' C6' C5' 118.3(4) . . ? C1' C6' C7' 120.7(4) . . ? C5' C6' C7' 120.6(4) . . ? O2' C7' C6' 124.6(5) . . ? O2' C7' C8' 120.4(4) . . ? C6' C7' C8' 115.0(4) . . ? O3' C8' C9' 59.6(3) . . ? O3' C8' C7' 117.9(4) . . ? C9' C8' C7' 120.5(4) . . ? O3' C8' C13' 115.3(4) . . ? C9' C8' C13' 112.2(4) . . ? C7' C8' C13' 118.2(4) . . ? O3' C9' C8' 59.4(3) . . ? O3' C9' C10' 118.4(4) . . ? C8' C9' C10' 112.4(4) . . ? C9' C10' C15' 108.5(4) . . ? C9' C10' C11' 102.9(4) . . ? C15' C10' C11' 109.1(4) . . ? C12' C11' C10' 110.4(4) . . ? C11' C12' C13' 107.7(3) . . ? C11' C12' C16' 114.5(4) . . ? C13' C12' C16' 102.4(3) . . ? O1' C13' C8' 112.0(3) . . ? O1' C13' C14' 107.6(3) . . ? C8' C13' C14' 114.1(4) . . ? O1' C13' C12' 112.0(3) . . ? C8' C13' C12' 112.0(3) . . ? C14' C13' C12' 98.4(3) . . ? O5' C14' C19' 108.0(4) . . ? O5' C14' C13' 103.5(3) . . ? C19' C14' C13' 116.2(4) . . ? O5' C14' C15' 108.4(4) . . ? C19' C14' C15' 114.0(4) . . ? C13' C14' C15' 106.2(4) . . ? O4' C15' C10' 124.7(5) . . ? O4' C15' C14' 120.9(4) . . ? C10' C15' C14' 114.2(4) . . ? O5' C16' C17' 107.6(4) . . ? O5' C16' C18' 107.3(4) . . ? C17' C16' C18' 110.1(4) . . ? O5' C16' C12' 103.9(3) . . ? C17' C16' C12' 115.4(4) . . ? C18' C16' C12' 112.0(4) . . ? C20' C19' C14' 112.8(4) . . ? C21' C20' C19' 126.1(5) . . ? C20' C21' C22' 116.3(5) . . ? C20' C21' C23' 126.5(5) . . ? C22' C21' C23' 117.2(5) . . ? O6' C22' C21' 125.4(5) . . ? C1 O1 C13 119.5(3) . . ? C9 O3 C8 60.6(3) . . ? C14 O5 C16 110.3(3) . . ? C1' O1' C13' 118.2(3) . . ? C8' O3' C9' 61.0(3) . . ? C14' O5' C16' 109.8(3) . . ? _diffrn_measured_fraction_theta_max 0.792 _diffrn_reflns_theta_full 60.00 _diffrn_measured_fraction_theta_full 0.959 _refine_diff_density_max 0.619 _refine_diff_density_min -0.309 _refine_diff_density_rms 0.080 data_theod24 _database_code_depnum_ccdc_archive 'CCDC 737626' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C28 H35 N O4' _chemical_formula_weight 449.57 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _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 9.8106(7) _cell_length_b 10.1395(8) _cell_length_c 12.1918(9) _cell_angle_alpha 106.4770(10) _cell_angle_beta 93.9620(10) _cell_angle_gamma 92.8280(10) _cell_volume 1157.17(15) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 6169 _cell_measurement_theta_min 2.31 _cell_measurement_theta_max 27.50 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.30 _exptl_crystal_density_diffrn 1.290 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 484 _exptl_absorpt_coefficient_mu 0.085 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9667 _exptl_absorpt_correction_T_max 0.9749 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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_reflns_number 9915 _diffrn_reflns_av_R_equivalents 0.0157 _diffrn_reflns_av_sigmaI/netI 0.0256 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.75 _diffrn_reflns_theta_max 27.50 _reflns_number_total 5073 _reflns_number_gt 4408 _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^)+(0.0700P)^2^+0.4000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_number_reflns 5073 _refine_ls_number_parameters 298 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0530 _refine_ls_R_factor_gt 0.0468 _refine_ls_wR_factor_ref 0.1308 _refine_ls_wR_factor_gt 0.1261 _refine_ls_goodness_of_fit_ref 1.095 _refine_ls_restrained_S_all 1.095 _refine_ls_shift/su_max 0.011 _refine_ls_shift/su_mean 0.002 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 0.29333(11) 0.72573(11) 0.48866(9) 0.0160(2) Uani 1 1 d . . . O1 O 0.14476(9) 0.94212(9) 0.84656(8) 0.0159(2) Uani 1 1 d . . . O2 O 0.40537(11) 1.10511(10) 0.66352(9) 0.0239(2) Uani 1 1 d . . . O3 O 0.30252(11) 0.50478(10) 0.65457(9) 0.0233(2) Uani 1 1 d . . . O4 O 0.22651(10) 0.68891(10) 0.87440(8) 0.0180(2) Uani 1 1 d . . . C1 C 0.38040(15) 0.62232(14) 0.42279(12) 0.0201(3) Uani 1 1 d . . . H1A H 0.4089 0.5611 0.4693 0.024 Uiso 1 1 calc R . . H1B H 0.4640 0.6698 0.4067 0.024 Uiso 1 1 calc R . . C2 C 0.30512(16) 0.53606(15) 0.31015(12) 0.0236(3) Uani 1 1 d . . . H2A H 0.2248 0.4838 0.3263 0.028 Uiso 1 1 calc R . . H2B H 0.3666 0.4689 0.2677 0.028 Uiso 1 1 calc R . . C3 C 0.25756(17) 0.62633(16) 0.23633(12) 0.0257(3) Uani 1 1 d . . . H3A H 0.2027 0.5693 0.1662 0.031 Uiso 1 1 calc R . . H3B H 0.3377 0.6715 0.2129 0.031 Uiso 1 1 calc R . . C4 C 0.17102(16) 0.73481(15) 0.30632(12) 0.0238(3) Uani 1 1 d . . . H4A H 0.1442 0.7983 0.2614 0.029 Uiso 1 1 calc R . . H4B H 0.0864 0.6893 0.3229 0.029 Uiso 1 1 calc R . . C5 C 0.25086(15) 0.81636(14) 0.41860(12) 0.0197(3) Uani 1 1 d . . . H5A H 0.3331 0.8652 0.4017 0.024 Uiso 1 1 calc R . . H5B H 0.1931 0.8864 0.4627 0.024 Uiso 1 1 calc R . . C6 C 0.36761(13) 0.80950(13) 0.59730(11) 0.0155(3) Uani 1 1 d . . . H6A H 0.4429 0.8683 0.5795 0.019 Uiso 1 1 calc R . . C7 C 0.43002(13) 0.71997(14) 0.66848(11) 0.0166(3) Uani 1 1 d . . . H7A H 0.5011 0.6630 0.6269 0.020 Uiso 1 1 calc R . . C8 C 0.49344(14) 0.82100(14) 0.78284(11) 0.0173(3) Uani 1 1 d . . . H8A H 0.5605 0.7741 0.8202 0.021 Uiso 1 1 calc R . . H8B H 0.5426 0.9006 0.7673 0.021 Uiso 1 1 calc R . . C9 C 0.38149(13) 0.87229(13) 0.86361(11) 0.0159(3) Uani 1 1 d . . . H9A H 0.4059 0.9693 0.9119 0.019 Uiso 1 1 calc R . . C10 C 0.24861(13) 0.86373(13) 0.78501(11) 0.0143(3) Uani 1 1 d . . . C11 C 0.27103(13) 0.90428(13) 0.67472(11) 0.0144(3) Uani 1 1 d . . . H11A H 0.1798 0.8923 0.6298 0.017 Uiso 1 1 calc R . . C12 C 0.31659(14) 1.05714(13) 0.70867(11) 0.0162(3) Uani 1 1 d . . . C13 C 0.24008(13) 1.14360(13) 0.79979(11) 0.0156(3) Uani 1 1 d . . . C14 C 0.24497(14) 1.28709(14) 0.82083(12) 0.0181(3) Uani 1 1 d . . . H14A H 0.3014 1.3299 0.7786 0.022 Uiso 1 1 calc R . . C15 C 0.16876(15) 1.36695(14) 0.90225(12) 0.0212(3) Uani 1 1 d . . . H15A H 0.1718 1.4641 0.9155 0.025 Uiso 1 1 calc R . . C16 C 0.08710(15) 1.30349(15) 0.96493(12) 0.0222(3) Uani 1 1 d . . . H16A H 0.0345 1.3582 1.0210 0.027 Uiso 1 1 calc R . . C17 C 0.08167(14) 1.16222(14) 0.94663(12) 0.0195(3) Uani 1 1 d . . . H17A H 0.0270 1.1203 0.9906 0.023 Uiso 1 1 calc R . . C18 C 0.15723(13) 1.08182(13) 0.86303(11) 0.0155(3) Uani 1 1 d . . . C19 C 0.31220(14) 0.62899(14) 0.68825(11) 0.0167(3) Uani 1 1 d . . . C20 C 0.34282(14) 0.77852(14) 0.93973(11) 0.0177(3) Uani 1 1 d . . . C21 C 0.45318(15) 0.68647(15) 0.96272(13) 0.0229(3) Uani 1 1 d . . . H21A H 0.4185 0.6303 1.0096 0.034 Uiso 1 1 calc R . . H21B H 0.5345 0.7440 1.0037 0.034 Uiso 1 1 calc R . . H21C H 0.4774 0.6260 0.8896 0.034 Uiso 1 1 calc R . . C22 C 0.29375(15) 0.86125(15) 1.05311(12) 0.0215(3) Uani 1 1 d . . . H22A H 0.2684 0.7987 1.0978 0.032 Uiso 1 1 calc R . . H22B H 0.2139 0.9098 1.0379 0.032 Uiso 1 1 calc R . . H22C H 0.3674 0.9285 1.0965 0.032 Uiso 1 1 calc R . . C23 C 0.20487(13) 0.71085(13) 0.76316(11) 0.0156(3) Uani 1 1 d . . . C24 C 0.05628(14) 0.65912(14) 0.72052(12) 0.0183(3) Uani 1 1 d . . . H24A H 0.0469 0.5586 0.7101 0.022 Uiso 1 1 calc R . . H24B H -0.0028 0.7031 0.7812 0.022 Uiso 1 1 calc R . . C25 C 0.00292(14) 0.68492(14) 0.61057(12) 0.0175(3) Uani 1 1 d . . . H25A H 0.0403 0.6353 0.5423 0.021 Uiso 1 1 calc R . . C26 C -0.09219(14) 0.77116(14) 0.59995(12) 0.0189(3) Uani 1 1 d . . . C27 C -0.13793(16) 0.78813(16) 0.48498(13) 0.0254(3) Uani 1 1 d . . . H27A H -0.0884 0.7278 0.4256 0.038 Uiso 1 1 calc R . . H27B H -0.1187 0.8843 0.4860 0.038 Uiso 1 1 calc R . . H27C H -0.2365 0.7634 0.4682 0.038 Uiso 1 1 calc R . . C28 C -0.16048(18) 0.86072(19) 0.69811(14) 0.0328(4) Uani 1 1 d . . . H28A H -0.1249 0.8451 0.7701 0.049 Uiso 1 1 calc R . . H28B H -0.2596 0.8377 0.6861 0.049 Uiso 1 1 calc R . . H28C H -0.1415 0.9578 0.7021 0.049 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 0.0202(6) 0.0139(5) 0.0139(5) 0.0036(4) 0.0023(4) 0.0038(4) O1 0.0179(5) 0.0116(5) 0.0192(5) 0.0048(4) 0.0063(4) 0.0021(4) O2 0.0262(5) 0.0179(5) 0.0299(6) 0.0083(4) 0.0117(4) 0.0006(4) O3 0.0309(6) 0.0138(5) 0.0245(5) 0.0042(4) 0.0022(4) 0.0037(4) O4 0.0226(5) 0.0158(5) 0.0161(5) 0.0069(4) -0.0015(4) -0.0023(4) C1 0.0248(7) 0.0183(7) 0.0173(7) 0.0040(5) 0.0039(5) 0.0070(5) C2 0.0352(8) 0.0183(7) 0.0164(7) 0.0026(5) 0.0031(6) 0.0074(6) C3 0.0372(9) 0.0250(8) 0.0150(7) 0.0045(6) 0.0034(6) 0.0095(6) C4 0.0311(8) 0.0245(7) 0.0166(7) 0.0063(6) 0.0007(6) 0.0083(6) C5 0.0272(7) 0.0167(7) 0.0171(7) 0.0066(5) 0.0034(5) 0.0063(5) C6 0.0178(6) 0.0135(6) 0.0153(6) 0.0039(5) 0.0031(5) 0.0022(5) C7 0.0171(6) 0.0160(6) 0.0163(6) 0.0036(5) 0.0021(5) 0.0042(5) C8 0.0166(6) 0.0177(7) 0.0170(6) 0.0041(5) 0.0006(5) 0.0010(5) C9 0.0182(6) 0.0139(6) 0.0154(6) 0.0037(5) 0.0014(5) 0.0006(5) C10 0.0152(6) 0.0130(6) 0.0150(6) 0.0036(5) 0.0037(5) 0.0017(5) C11 0.0157(6) 0.0133(6) 0.0144(6) 0.0041(5) 0.0019(5) 0.0014(5) C12 0.0173(6) 0.0150(6) 0.0170(6) 0.0064(5) 0.0006(5) 0.0008(5) C13 0.0173(6) 0.0140(6) 0.0155(6) 0.0044(5) 0.0003(5) 0.0007(5) C14 0.0208(7) 0.0159(6) 0.0186(7) 0.0070(5) 0.0004(5) -0.0006(5) C15 0.0287(7) 0.0124(6) 0.0221(7) 0.0043(5) 0.0008(6) 0.0025(5) C16 0.0271(7) 0.0187(7) 0.0205(7) 0.0034(5) 0.0061(6) 0.0064(6) C17 0.0220(7) 0.0183(7) 0.0193(7) 0.0061(5) 0.0050(5) 0.0024(5) C18 0.0172(6) 0.0130(6) 0.0161(6) 0.0042(5) -0.0001(5) 0.0010(5) C19 0.0208(7) 0.0152(6) 0.0143(6) 0.0054(5) -0.0021(5) 0.0032(5) C20 0.0202(7) 0.0162(6) 0.0162(6) 0.0047(5) -0.0005(5) -0.0007(5) C21 0.0261(7) 0.0241(7) 0.0208(7) 0.0100(6) 0.0002(6) 0.0045(6) C22 0.0254(7) 0.0212(7) 0.0176(7) 0.0052(5) 0.0023(5) -0.0004(6) C23 0.0187(6) 0.0136(6) 0.0154(6) 0.0059(5) 0.0005(5) 0.0009(5) C24 0.0190(7) 0.0139(6) 0.0221(7) 0.0060(5) 0.0007(5) -0.0019(5) C25 0.0177(6) 0.0153(6) 0.0180(6) 0.0028(5) 0.0013(5) -0.0014(5) C26 0.0171(6) 0.0175(6) 0.0217(7) 0.0054(5) 0.0016(5) -0.0012(5) C27 0.0253(7) 0.0255(8) 0.0263(8) 0.0098(6) -0.0021(6) 0.0033(6) C28 0.0301(8) 0.0390(9) 0.0307(8) 0.0091(7) 0.0073(7) 0.0159(7) _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 C6 1.4745(17) . ? N1 C1 1.4762(17) . ? N1 C5 1.4770(17) . ? O1 C18 1.3711(15) . ? O1 C10 1.4423(15) . ? O2 C12 1.2143(16) . ? O3 C19 1.2055(17) . ? O4 C23 1.4387(16) . ? O4 C20 1.4572(16) . ? C1 C2 1.5202(19) . ? C2 C3 1.522(2) . ? C3 C4 1.523(2) . ? C4 C5 1.522(2) . ? C6 C7 1.5430(18) . ? C6 C11 1.5528(17) . ? C7 C19 1.5181(19) . ? C7 C8 1.5451(18) . ? C8 C9 1.5368(18) . ? C9 C10 1.5473(18) . ? C9 C20 1.5565(18) . ? C10 C23 1.5305(18) . ? C10 C11 1.5399(18) . ? C11 C12 1.5217(18) . ? C12 C13 1.4811(18) . ? C13 C14 1.4016(18) . ? C13 C18 1.3992(18) . ? C14 C15 1.3808(19) . ? C15 C16 1.397(2) . ? C16 C17 1.383(2) . ? C17 C18 1.3949(19) . ? C19 C23 1.5559(18) . ? C20 C22 1.5233(19) . ? C20 C21 1.5259(19) . ? C23 C24 1.5282(18) . ? C24 C25 1.5016(19) . ? C25 C26 1.334(2) . ? C26 C27 1.501(2) . ? C26 C28 1.503(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C6 N1 C1 111.01(10) . . ? C6 N1 C5 109.53(10) . . ? C1 N1 C5 109.04(10) . . ? C18 O1 C10 116.41(10) . . ? C23 O4 C20 109.66(10) . . ? N1 C1 C2 111.43(11) . . ? C1 C2 C3 111.19(12) . . ? C2 C3 C4 108.43(12) . . ? C5 C4 C3 110.50(12) . . ? N1 C5 C4 111.53(11) . . ? N1 C6 C7 112.31(10) . . ? N1 C6 C11 111.31(10) . . ? C7 C6 C11 106.53(10) . . ? C19 C7 C6 106.45(10) . . ? C19 C7 C8 111.13(11) . . ? C6 C7 C8 106.28(10) . . ? C9 C8 C7 110.55(11) . . ? C8 C9 C10 105.95(10) . . ? C8 C9 C20 115.22(11) . . ? C10 C9 C20 103.25(10) . . ? O1 C10 C23 107.47(10) . . ? O1 C10 C11 110.69(10) . . ? C23 C10 C11 113.61(11) . . ? O1 C10 C9 111.60(10) . . ? C23 C10 C9 98.93(10) . . ? C11 C10 C9 113.91(10) . . ? C12 C11 C10 108.18(10) . . ? C12 C11 C6 114.45(10) . . ? C10 C11 C6 112.62(10) . . ? O2 C12 C13 122.65(12) . . ? O2 C12 C11 123.32(12) . . ? C13 C12 C11 114.01(11) . . ? C14 C13 C18 119.09(12) . . ? C14 C13 C12 120.82(12) . . ? C18 C13 C12 120.04(12) . . ? C15 C14 C13 120.77(12) . . ? C14 C15 C16 119.33(13) . . ? C17 C16 C15 121.01(13) . . ? C16 C17 C18 119.42(13) . . ? O1 C18 C17 116.77(11) . . ? O1 C18 C13 122.85(12) . . ? C17 C18 C13 120.38(12) . . ? O3 C19 C7 124.78(13) . . ? O3 C19 C23 121.60(12) . . ? C7 C19 C23 113.55(11) . . ? O4 C20 C22 107.30(11) . . ? O4 C20 C21 107.58(11) . . ? C22 C20 C21 109.57(11) . . ? O4 C20 C9 104.39(10) . . ? C22 C20 C9 111.79(11) . . ? C21 C20 C9 115.68(11) . . ? O4 C23 C10 103.86(10) . . ? O4 C23 C24 105.71(10) . . ? C10 C23 C24 119.28(11) . . ? O4 C23 C19 106.45(10) . . ? C10 C23 C19 106.32(10) . . ? C24 C23 C19 114.07(11) . . ? C25 C24 C23 116.21(11) . . ? C26 C25 C24 125.96(13) . . ? C25 C26 C27 121.21(13) . . ? C25 C26 C28 124.73(13) . . ? C27 C26 C28 114.06(13) . . ? _diffrn_measured_fraction_theta_max 0.952 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.952 _refine_diff_density_max 0.422 _refine_diff_density_min -0.351 _refine_diff_density_rms 0.053