Supplementary Material for Organic & Biomolecular Chemistry This journal is (c) The Royal Society of Chemistry 2007 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_cambridge 0177 _publ_section_title ;Synthesis of alkylated sugar amino acids: conformationally restricted L-Xaa-L-Ser/Thr mimicks ; _publ_contact_author_name 'Mark Overhand' _publ_contact_author_email OVERHAND@CHEM.LEIDENUNIV.NL loop_ _publ_author_name 'Mark Overhand' 'Jaroslaw Mazurek' 'Herman S Overkleeft' 'Martijn D.P. Risseeuw' ; G.A.van der Marel ; 'A.van Langenvelde' data_leiden_sugar _database_code_depnum_ccdc_archive 'CCDC 644038' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C39 H46 O6' _chemical_formula_weight 610.76 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting ? _symmetry_space_group_name_H-M ? loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' _cell_length_a 6.05200(10) _cell_length_b 23.7560(5) _cell_length_c 23.9440(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3442.46(12) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.178 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1312 _exptl_absorpt_coefficient_mu 0.078 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 17437 _diffrn_reflns_av_R_equivalents 0.0411 _diffrn_reflns_av_sigmaI/netI 0.0567 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -30 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_limit_l_max 31 _diffrn_reflns_theta_min 3.07 _diffrn_reflns_theta_max 27.50 _reflns_number_total 7673 _reflns_number_gt 5455 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0351P)^2^+0.1224P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.4(7) _refine_ls_number_reflns 7673 _refine_ls_number_parameters 566 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0747 _refine_ls_R_factor_gt 0.0465 _refine_ls_wR_factor_ref 0.0965 _refine_ls_wR_factor_gt 0.0858 _refine_ls_goodness_of_fit_ref 1.025 _refine_ls_restrained_S_all 1.025 _refine_ls_shift/su_max 0.004 _refine_ls_shift/su_mean 0.001 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 0.3348(3) 0.17670(7) 0.35042(6) 0.0423(4) Uani 1 1 d . . . H1 H 0.232(3) 0.1444(7) 0.3460(6) 0.046(4) Uiso 1 1 d . . . C2 C 0.4694(3) 0.16660(7) 0.40344(7) 0.0488(4) Uani 1 1 d . . . H2 H 0.353(3) 0.1605(7) 0.4343(7) 0.048(4) Uiso 1 1 d . . . O3 O 0.5980(2) 0.21512(5) 0.41694(5) 0.0565(3) Uani 1 1 d . . . H3 H 0.729(5) 0.2103(11) 0.3980(11) 0.114(9) Uiso 1 1 d . . . C4 C 0.6149(4) 0.11468(8) 0.40006(9) 0.0624(5) Uani 1 1 d . . . H4A H 0.690(3) 0.1113(7) 0.4369(8) 0.059(5) Uiso 1 1 d . . . H4B H 0.731(3) 0.1251(8) 0.3695(8) 0.064(5) Uiso 1 1 d . . . C5 C 0.5026(4) 0.05950(9) 0.38520(10) 0.0810(7) Uani 1 1 d . . . H5 H 0.423(3) 0.0658(8) 0.3472(8) 0.070(5) Uiso 1 1 d . . . C6 C 0.3260(6) 0.04333(13) 0.42693(14) 0.1336(12) Uani 1 1 d . . . H6A H 0.2593 0.0084 0.4158 0.200 Uiso 1 1 calc R . . H6B H 0.2153 0.0722 0.4282 0.200 Uiso 1 1 calc R . . H6C H 0.3914 0.0391 0.4632 0.200 Uiso 1 1 calc R . . C7 C 0.6758(6) 0.01294(12) 0.38021(16) 0.1420(13) Uani 1 1 d . . . H7A H 0.7856 0.0238 0.3534 0.213 Uiso 1 1 calc R . . H7B H 0.6057 -0.0213 0.3683 0.213 Uiso 1 1 calc R . . H7C H 0.7447 0.0071 0.4158 0.213 Uiso 1 1 calc R . . C8 C 0.2121(3) 0.23265(7) 0.34825(6) 0.0405(4) Uani 1 1 d . . . H8 H 0.315(2) 0.2627(6) 0.3539(5) 0.031(4) Uiso 1 1 d . . . O9 O 0.04621(17) 0.23512(5) 0.39048(4) 0.0482(3) Uani 1 1 d . . . C10 C 0.1046(4) 0.26474(8) 0.44085(7) 0.0552(5) Uani 1 1 d . . . H10A H 0.251(3) 0.2507(8) 0.4567(8) 0.066(6) Uiso 1 1 d . . . H10B H -0.018(3) 0.2544(8) 0.4667(8) 0.072(6) Uiso 1 1 d . . . C11 C 0.1161(3) 0.32731(8) 0.43349(7) 0.0539(5) Uani 1 1 d . . . C12 C 0.3084(4) 0.35547(11) 0.44669(10) 0.0786(6) Uani 1 1 d . . . H12 H 0.441(4) 0.3343(8) 0.4600(8) 0.075(6) Uiso 1 1 d . . . C13 C 0.3197(7) 0.41320(15) 0.44207(14) 0.1057(9) Uani 1 1 d . . . H13 H 0.481(6) 0.4310(13) 0.4535(12) 0.142(11) Uiso 1 1 d . . . C14 C 0.1424(8) 0.44275(13) 0.42295(12) 0.1064(10) Uani 1 1 d . . . H14 H 0.142(5) 0.4848(14) 0.4171(12) 0.146(11) Uiso 1 1 d . . . C15 C -0.0469(7) 0.41538(12) 0.40879(13) 0.1012(9) Uani 1 1 d . . . H15 H -0.175(5) 0.4318(12) 0.3994(11) 0.101(9) Uiso 1 1 d . . . C16 C -0.0618(5) 0.35739(10) 0.41477(11) 0.0800(6) Uani 1 1 d . . . H16 H -0.195(4) 0.3378(9) 0.4101(9) 0.086(7) Uiso 1 1 d . . . C17 C 0.0962(3) 0.23964(7) 0.29221(6) 0.0425(4) Uani 1 1 d . . . H17 H -0.030(3) 0.2149(6) 0.2922(6) 0.041(4) Uiso 1 1 d . . . O18 O 0.02351(17) 0.29658(4) 0.28642(5) 0.0492(3) Uani 1 1 d . . . C19 C -0.2079(3) 0.30445(9) 0.28263(11) 0.0599(5) Uani 1 1 d . . . H19A H -0.289(3) 0.2878(7) 0.3142(8) 0.059(5) Uiso 1 1 d . . . H19B H -0.264(4) 0.2824(9) 0.2508(9) 0.085(7) Uiso 1 1 d . . . C20 C -0.2602(3) 0.36522(7) 0.27493(7) 0.0522(4) Uani 1 1 d . . . C21 C -0.4649(3) 0.38563(9) 0.29019(9) 0.0673(5) Uani 1 1 d . . . H21 H -0.571(4) 0.3596(9) 0.3063(9) 0.090(7) Uiso 1 1 d . . . C22 C -0.5202(4) 0.44103(10) 0.28245(11) 0.0802(7) Uani 1 1 d . . . H22 H -0.668(4) 0.4565(9) 0.2927(9) 0.093(7) Uiso 1 1 d . . . C23 C -0.3717(5) 0.47738(11) 0.25868(10) 0.0848(7) Uani 1 1 d . . . H23 H -0.401(4) 0.5149(10) 0.2539(9) 0.091(7) Uiso 1 1 d . . . C24 C -0.1688(5) 0.45804(10) 0.24254(11) 0.0881(7) Uani 1 1 d . . . H24 H -0.045(4) 0.4838(10) 0.2249(10) 0.102(8) Uiso 1 1 d . . . C25 C -0.1123(4) 0.40216(9) 0.25088(10) 0.0721(6) Uani 1 1 d . . . H25 H 0.034(4) 0.3881(9) 0.2416(9) 0.089(7) Uiso 1 1 d . . . C26 C 0.2446(3) 0.22557(8) 0.24269(6) 0.0439(4) Uani 1 1 d . . . H26 H 0.346(2) 0.2573(6) 0.2372(5) 0.033(4) Uiso 1 1 d . . . O27 O 0.1135(2) 0.21734(5) 0.19368(4) 0.0598(3) Uani 1 1 d . . . C28 C 0.0864(4) 0.26534(13) 0.15867(10) 0.0785(7) Uani 1 1 d . . . H28A H 0.028(4) 0.2967(9) 0.1801(9) 0.086(7) Uiso 1 1 d . . . H28B H -0.028(4) 0.2575(10) 0.1326(11) 0.104(8) Uiso 1 1 d . . . C29 C 0.2908(4) 0.28062(9) 0.12640(7) 0.0645(5) Uani 1 1 d . . . C30 C 0.4059(5) 0.32909(11) 0.13783(10) 0.0813(7) Uani 1 1 d . . . H30 H 0.356(4) 0.3525(10) 0.1674(10) 0.105(9) Uiso 1 1 d . . . C31 C 0.5954(6) 0.34283(13) 0.10756(13) 0.0924(8) Uani 1 1 d . . . H31 H 0.667(5) 0.3747(12) 0.1147(11) 0.120(11) Uiso 1 1 d . . . C32 C 0.6669(5) 0.30856(13) 0.06539(12) 0.0873(7) Uani 1 1 d . . . H32 H 0.817(5) 0.3186(10) 0.0439(10) 0.106(8) Uiso 1 1 d . . . C33 C 0.5553(5) 0.26044(12) 0.05435(10) 0.0823(7) Uani 1 1 d . . . H33 H 0.606(4) 0.2381(10) 0.0240(9) 0.096(8) Uiso 1 1 d . . . C34 C 0.3693(4) 0.24656(10) 0.08412(8) 0.0703(6) Uani 1 1 d . . . H34 H 0.292(4) 0.2134(10) 0.0778(9) 0.089(8) Uiso 1 1 d . . . C35 C 0.3730(3) 0.17137(7) 0.25205(6) 0.0441(4) Uani 1 1 d . . . H35 H 0.271(3) 0.1396(7) 0.2533(7) 0.051(5) Uiso 1 1 d . . . C36 C 0.5428(4) 0.16145(7) 0.20755(8) 0.0526(4) Uani 1 1 d . . . H36A H 0.477(3) 0.1670(6) 0.1713(7) 0.048(5) Uiso 1 1 d . . . H36B H 0.663(3) 0.1881(8) 0.2101(8) 0.064(6) Uiso 1 1 d . . . O37 O 0.6230(2) 0.10548(5) 0.21232(5) 0.0649(4) Uani 1 1 d . . . C38 C 0.7835(4) 0.09306(11) 0.17070(10) 0.0739(6) Uani 1 1 d . . . H38A H 0.846(4) 0.0578(10) 0.1834(9) 0.088(7) Uiso 1 1 d . . . H38B H 0.908(4) 0.1227(9) 0.1720(9) 0.087(7) Uiso 1 1 d . . . C39 C 0.6920(3) 0.09065(7) 0.11281(8) 0.0584(5) Uani 1 1 d . . . C40 C 0.8084(5) 0.11069(11) 0.06712(13) 0.0874(8) Uani 1 1 d . . . H40 H 0.931(5) 0.1234(11) 0.0806(11) 0.105(10) Uiso 1 1 d . . . C41 C 0.7236(8) 0.10483(14) 0.01330(13) 0.1118(13) Uani 1 1 d . . . H41 H 0.786(5) 0.1197(13) -0.0120(14) 0.126(12) Uiso 1 1 d . . . C42 C 0.5270(8) 0.08022(14) 0.00500(14) 0.1067(10) Uani 1 1 d . . . H42 H 0.490(5) 0.0806(12) -0.0361(13) 0.134(11) Uiso 1 1 d . . . C43 C 0.4095(6) 0.06074(12) 0.04828(12) 0.0920(8) Uani 1 1 d . . . H43 H 0.264(5) 0.0438(12) 0.0418(12) 0.127(11) Uiso 1 1 d . . . C44 C 0.4906(4) 0.06628(9) 0.10183(10) 0.0723(6) Uani 1 1 d . . . H44 H 0.410(4) 0.0518(8) 0.1335(9) 0.077(6) Uiso 1 1 d . . . O45 O 0.48451(17) 0.17413(4) 0.30424(4) 0.0454(3) 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 0.0417(9) 0.0466(10) 0.0386(9) 0.0002(7) 0.0023(7) -0.0038(8) C2 0.0464(9) 0.0558(10) 0.0442(9) 0.0028(8) -0.0007(8) -0.0059(9) O3 0.0474(7) 0.0678(8) 0.0543(7) -0.0091(6) -0.0047(6) -0.0087(6) C4 0.0668(12) 0.0646(12) 0.0559(12) 0.0052(10) -0.0115(12) 0.0087(11) C5 0.1013(18) 0.0620(13) 0.0796(15) 0.0046(11) -0.0253(14) 0.0063(13) C6 0.158(3) 0.109(2) 0.134(3) 0.0326(19) -0.014(2) -0.054(2) C7 0.161(3) 0.0783(18) 0.187(3) -0.0150(19) -0.060(3) 0.036(2) C8 0.0364(8) 0.0454(10) 0.0396(8) -0.0020(7) 0.0019(7) -0.0071(8) O9 0.0407(6) 0.0596(7) 0.0444(6) -0.0064(5) 0.0079(5) -0.0079(5) C10 0.0584(11) 0.0653(12) 0.0420(9) -0.0087(9) 0.0050(10) -0.0044(10) C11 0.0567(11) 0.0626(12) 0.0425(9) -0.0102(9) 0.0113(9) -0.0093(10) C12 0.0746(15) 0.0819(18) 0.0794(15) -0.0061(13) 0.0085(13) -0.0183(14) C13 0.114(2) 0.091(2) 0.113(2) -0.0102(18) 0.022(2) -0.038(2) C14 0.158(3) 0.0671(19) 0.0938(19) -0.0076(15) 0.030(2) -0.024(2) C15 0.127(3) 0.078(2) 0.099(2) -0.0162(15) 0.002(2) 0.028(2) C16 0.0776(16) 0.0663(15) 0.0960(17) -0.0190(12) -0.0077(14) 0.0090(14) C17 0.0388(8) 0.0429(9) 0.0458(9) 0.0004(8) -0.0022(8) -0.0056(8) O18 0.0397(6) 0.0448(6) 0.0631(7) 0.0022(6) -0.0027(5) 0.0000(5) C19 0.0390(9) 0.0585(12) 0.0823(14) 0.0017(12) 0.0031(10) 0.0027(9) C20 0.0501(10) 0.0531(11) 0.0533(10) -0.0002(8) -0.0013(8) 0.0043(9) C21 0.0555(11) 0.0617(12) 0.0846(14) -0.0004(11) 0.0058(11) 0.0107(11) C22 0.0704(14) 0.0723(15) 0.0980(17) -0.0039(13) 0.0028(13) 0.0228(13) C23 0.111(2) 0.0590(14) 0.0844(15) 0.0082(12) 0.0010(16) 0.0282(15) C24 0.1028(19) 0.0633(15) 0.0982(17) 0.0171(13) 0.0242(16) 0.0051(15) C25 0.0654(13) 0.0610(13) 0.0900(16) 0.0066(11) 0.0157(13) 0.0074(12) C26 0.0406(9) 0.0524(10) 0.0387(8) 0.0008(8) -0.0048(7) -0.0052(8) O27 0.0571(7) 0.0807(9) 0.0415(6) 0.0023(6) -0.0128(6) -0.0040(7) C28 0.0718(15) 0.113(2) 0.0504(12) 0.0208(14) -0.0060(12) 0.0243(15) C29 0.0817(14) 0.0708(14) 0.0408(10) 0.0116(10) -0.0094(10) 0.0184(12) C30 0.109(2) 0.0785(16) 0.0569(13) 0.0055(13) -0.0085(14) 0.0191(17) C31 0.108(2) 0.0766(17) 0.0926(19) 0.0186(16) -0.0197(19) -0.0102(17) C32 0.0857(18) 0.096(2) 0.0801(17) 0.0241(16) -0.0038(15) 0.0051(16) C33 0.1015(19) 0.0890(18) 0.0564(13) 0.0108(13) 0.0105(14) 0.0160(16) C34 0.0866(16) 0.0732(15) 0.0511(11) 0.0044(11) -0.0008(12) 0.0036(13) C35 0.0505(9) 0.0434(9) 0.0382(9) -0.0026(8) -0.0020(8) -0.0063(9) C36 0.0649(12) 0.0469(10) 0.0459(10) -0.0036(9) 0.0028(10) 0.0046(10) O37 0.0855(9) 0.0532(7) 0.0559(7) -0.0037(6) 0.0049(7) 0.0182(7) C38 0.0692(14) 0.0725(16) 0.0799(15) -0.0193(13) -0.0016(12) 0.0183(14) C39 0.0635(12) 0.0474(11) 0.0644(12) -0.0116(9) 0.0109(10) 0.0079(9) C40 0.0925(19) 0.0732(17) 0.097(2) -0.0099(14) 0.0283(17) -0.0091(15) C41 0.175(4) 0.092(2) 0.069(2) 0.0084(16) 0.049(2) 0.004(2) C42 0.152(3) 0.089(2) 0.079(2) -0.0011(16) -0.003(2) 0.023(2) C43 0.099(2) 0.0855(18) 0.091(2) -0.0221(15) -0.0093(18) 0.0090(16) C44 0.0757(15) 0.0740(14) 0.0674(15) -0.0085(12) 0.0078(13) 0.0019(12) O45 0.0443(6) 0.0546(6) 0.0373(6) -0.0022(5) -0.0013(5) 0.0018(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 C1 O45 1.4309(18) . ? C1 C8 1.523(2) . ? C1 C2 1.527(2) . ? C1 H1 0.995(16) . ? C2 O3 1.428(2) . ? C2 C4 1.518(3) . ? C2 H2 1.033(17) . ? O3 H3 0.92(3) . ? C4 C5 1.519(3) . ? C4 H4A 0.995(19) . ? C4 H4B 1.04(2) . ? C5 C6 1.513(4) . ? C5 C7 1.528(4) . ? C5 H5 1.042(19) . ? C6 H6A 0.9600 . ? C6 H6B 0.9600 . ? C6 H6C 0.9600 . ? C7 H7A 0.9600 . ? C7 H7B 0.9600 . ? C7 H7C 0.9600 . ? C8 O9 1.4261(18) . ? C8 C17 1.523(2) . ? C8 H8 0.957(15) . ? O9 C10 1.440(2) . ? C10 C11 1.498(3) . ? C10 H10A 1.02(2) . ? C10 H10B 1.00(2) . ? C11 C16 1.367(3) . ? C11 C12 1.379(3) . ? C12 C13 1.378(4) . ? C12 H12 1.00(2) . ? C13 C14 1.361(5) . ? C13 H13 1.10(3) . ? C14 C15 1.360(5) . ? C14 H14 1.01(3) . ? C15 C16 1.388(4) . ? C15 H15 0.89(3) . ? C16 H16 0.94(2) . ? C17 O18 1.4292(18) . ? C17 C26 1.525(2) . ? C17 H17 0.965(15) . ? O18 C19 1.416(2) . ? C19 C20 1.489(3) . ? C19 H19A 0.982(19) . ? C19 H19B 0.98(2) . ? C20 C21 1.380(3) . ? C20 C25 1.380(3) . ? C21 C22 1.371(3) . ? C21 H21 0.97(2) . ? C22 C23 1.370(4) . ? C22 H22 1.00(2) . ? C23 C24 1.367(4) . ? C23 H23 0.92(2) . ? C24 C25 1.385(3) . ? C24 H24 1.05(3) . ? C25 H25 0.97(2) . ? C26 O27 1.4301(18) . ? C26 C35 1.520(2) . ? C26 H26 0.981(15) . ? O27 C28 1.425(3) . ? C28 C29 1.503(3) . ? C28 H28A 0.97(2) . ? C28 H28B 0.95(3) . ? C29 C30 1.374(3) . ? C29 C34 1.380(3) . ? C30 C31 1.395(4) . ? C30 H30 0.95(2) . ? C31 C32 1.367(4) . ? C31 H31 0.89(3) . ? C32 C33 1.354(4) . ? C32 H32 1.07(3) . ? C33 C34 1.373(3) . ? C33 H33 0.95(2) . ? C34 H34 0.93(2) . ? C35 O45 1.4219(18) . ? C35 C36 1.499(2) . ? C35 H35 0.977(17) . ? C36 O37 1.420(2) . ? C36 H36A 0.964(17) . ? C36 H36B 0.96(2) . ? O37 C38 1.422(3) . ? C38 C39 1.494(3) . ? C38 H38A 0.97(2) . ? C38 H38B 1.03(2) . ? C39 C44 1.375(3) . ? C39 C40 1.386(3) . ? C40 C41 1.394(5) . ? C40 H40 0.86(3) . ? C41 C42 1.341(5) . ? C41 H41 0.80(3) . ? C42 C43 1.339(4) . ? C42 H42 1.01(3) . ? C43 C44 1.379(3) . ? C43 H43 0.98(3) . ? C44 H44 0.97(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 O45 C1 C8 108.64(12) . . ? O45 C1 C2 107.33(12) . . ? C8 C1 C2 115.17(13) . . ? O45 C1 H1 106.4(9) . . ? C8 C1 H1 111.3(9) . . ? C2 C1 H1 107.5(9) . . ? O3 C2 C4 110.58(15) . . ? O3 C2 C1 110.61(14) . . ? C4 C2 C1 113.14(15) . . ? O3 C2 H2 108.8(9) . . ? C4 C2 H2 108.8(9) . . ? C1 C2 H2 104.6(8) . . ? C2 O3 H3 104.9(16) . . ? C2 C4 C5 116.99(17) . . ? C2 C4 H4A 106.5(10) . . ? C5 C4 H4A 110.0(11) . . ? C2 C4 H4B 103.6(10) . . ? C5 C4 H4B 109.9(10) . . ? H4A C4 H4B 109.5(15) . . ? C6 C5 C4 112.4(2) . . ? C6 C5 C7 110.6(2) . . ? C4 C5 C7 109.6(2) . . ? C6 C5 H5 106.6(11) . . ? C4 C5 H5 106.8(10) . . ? C7 C5 H5 110.7(11) . . ? C5 C6 H6A 109.5 . . ? C5 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C5 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? C5 C7 H7A 109.5 . . ? C5 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C5 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? O9 C8 C1 110.78(13) . . ? O9 C8 C17 107.20(12) . . ? C1 C8 C17 110.46(13) . . ? O9 C8 H8 109.0(8) . . ? C1 C8 H8 109.2(8) . . ? C17 C8 H8 110.1(8) . . ? C8 O9 C10 116.16(13) . . ? O9 C10 C11 113.43(15) . . ? O9 C10 H10A 111.4(11) . . ? C11 C10 H10A 109.2(11) . . ? O9 C10 H10B 102.4(11) . . ? C11 C10 H10B 110.6(11) . . ? H10A C10 H10B 109.7(14) . . ? C16 C11 C12 119.1(2) . . ? C16 C11 C10 121.35(19) . . ? C12 C11 C10 119.6(2) . . ? C13 C12 C11 120.4(3) . . ? C13 C12 H12 119.3(12) . . ? C11 C12 H12 120.3(12) . . ? C14 C13 C12 120.1(3) . . ? C14 C13 H13 125.9(16) . . ? C12 C13 H13 114.0(17) . . ? C15 C14 C13 120.1(3) . . ? C15 C14 H14 115.9(19) . . ? C13 C14 H14 124.0(19) . . ? C14 C15 C16 120.2(3) . . ? C14 C15 H15 125.5(18) . . ? C16 C15 H15 113.8(18) . . ? C11 C16 C15 120.1(3) . . ? C11 C16 H16 117.2(14) . . ? C15 C16 H16 122.4(14) . . ? O18 C17 C8 109.29(12) . . ? O18 C17 C26 108.26(13) . . ? C8 C17 C26 112.93(13) . . ? O18 C17 H17 109.4(9) . . ? C8 C17 H17 107.4(9) . . ? C26 C17 H17 109.5(9) . . ? C19 O18 C17 115.82(13) . . ? O18 C19 C20 110.26(16) . . ? O18 C19 H19A 113.0(10) . . ? C20 C19 H19A 112.3(10) . . ? O18 C19 H19B 108.6(13) . . ? C20 C19 H19B 110.2(13) . . ? H19A C19 H19B 102.2(16) . . ? C21 C20 C25 118.02(18) . . ? C21 C20 C19 119.91(18) . . ? C25 C20 C19 122.02(17) . . ? C22 C21 C20 121.4(2) . . ? C22 C21 H21 120.3(13) . . ? C20 C21 H21 118.4(13) . . ? C23 C22 C21 120.1(2) . . ? C23 C22 H22 117.3(13) . . ? C21 C22 H22 122.6(13) . . ? C24 C23 C22 119.7(2) . . ? C24 C23 H23 117.9(16) . . ? C22 C23 H23 122.4(16) . . ? C23 C24 C25 120.2(3) . . ? C23 C24 H24 123.7(13) . . ? C25 C24 H24 116.1(13) . . ? C20 C25 C24 120.6(2) . . ? C20 C25 H25 118.0(13) . . ? C24 C25 H25 121.3(13) . . ? O27 C26 C35 106.78(13) . . ? O27 C26 C17 109.94(13) . . ? C35 C26 C17 111.84(13) . . ? O27 C26 H26 110.0(8) . . ? C35 C26 H26 110.6(8) . . ? C17 C26 H26 107.7(8) . . ? C28 O27 C26 115.94(17) . . ? O27 C28 C29 113.63(18) . . ? O27 C28 H28A 110.2(13) . . ? C29 C28 H28A 112.8(13) . . ? O27 C28 H28B 108.2(15) . . ? C29 C28 H28B 108.1(15) . . ? H28A C28 H28B 103.3(19) . . ? C30 C29 C34 117.6(2) . . ? C30 C29 C28 121.2(2) . . ? C34 C29 C28 121.2(2) . . ? C29 C30 C31 120.6(3) . . ? C29 C30 H30 118.6(16) . . ? C31 C30 H30 120.7(16) . . ? C32 C31 C30 120.3(3) . . ? C32 C31 H31 119.6(19) . . ? C30 C31 H31 120.1(19) . . ? C33 C32 C31 119.3(3) . . ? C33 C32 H32 121.1(14) . . ? C31 C32 H32 119.4(14) . . ? C32 C33 C34 120.7(3) . . ? C32 C33 H33 117.4(15) . . ? C34 C33 H33 121.8(15) . . ? C33 C34 C29 121.5(3) . . ? C33 C34 H34 122.1(14) . . ? C29 C34 H34 116.4(14) . . ? O45 C35 C36 107.85(14) . . ? O45 C35 C26 109.46(12) . . ? C36 C35 C26 112.24(13) . . ? O45 C35 H35 108.0(10) . . ? C36 C35 H35 109.5(9) . . ? C26 C35 H35 109.7(9) . . ? O37 C36 C35 108.94(15) . . ? O37 C36 H36A 110.0(9) . . ? C35 C36 H36A 109.7(10) . . ? O37 C36 H36B 110.7(11) . . ? C35 C36 H36B 111.6(11) . . ? H36A C36 H36B 106.0(15) . . ? C36 O37 C38 111.81(16) . . ? O37 C38 C39 113.89(18) . . ? O37 C38 H38A 103.2(13) . . ? C39 C38 H38A 113.8(13) . . ? O37 C38 H38B 109.7(12) . . ? C39 C38 H38B 108.9(12) . . ? H38A C38 H38B 107.1(18) . . ? C44 C39 C40 116.4(2) . . ? C44 C39 C38 121.5(2) . . ? C40 C39 C38 122.1(2) . . ? C39 C40 C41 120.6(3) . . ? C39 C40 H40 105.1(19) . . ? C41 C40 H40 134.3(19) . . ? C42 C41 C40 120.5(3) . . ? C42 C41 H41 120(2) . . ? C40 C41 H41 119(2) . . ? C43 C42 C41 120.5(3) . . ? C43 C42 H42 129.8(19) . . ? C41 C42 H42 109.7(19) . . ? C42 C43 C44 119.8(3) . . ? C42 C43 H43 119.8(18) . . ? C44 C43 H43 120.4(18) . . ? C39 C44 C43 122.2(3) . . ? C39 C44 H44 116.5(13) . . ? C43 C44 H44 121.2(13) . . ? C35 O45 C1 112.36(11) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O3 H3 O9 0.92(3) 2.02(3) 2.8259(17) 146(2) 1_655 _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.126 _refine_diff_density_min -0.116 _refine_diff_density_rms 0.022