#Supplementary Material (ESI) for Organic & Biomolecular Chemistry #This journal is (c) The Royal Society of Chemistry 2006 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_cambridge 0177 _publ_contact_author_name P.O'Neill _publ_contact_author_address ; The University of Liverpool Department of Chemistry Robert Robinson Laboratories LIVERPOOL L69 3BX UNITED KINGDOM ; _publ_section_title ; Design and Synthesis of Orally Active Dispiro 1, 2, 4, 5-Tetraoxanes; Synthetic Antimalarials with Superior Activity to Artemisinin ; _publ_contact_author_email P.M.ONEILL01@LIVERPOOL.AC.UK loop_ _publ_author_name P.O'Neill R.Amewu N.G.Barry P.G.Bray J.Davies G.Labat A.Stachulski S.A.Ward data_rka152 _database_code_depnum_ccdc_archive 'CCDC 616879' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety (C18H29NO6) _chemical_formula_sum 'C18 H29 N O6' _chemical_formula_weight 355.42 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 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 5.9604(12) _cell_length_b 8.5899(17) _cell_length_c 17.360(3) _cell_angle_alpha 92.596(4) _cell_angle_beta 95.039(4) _cell_angle_gamma 99.803(4) _cell_volume 870.8(3) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 5294 _cell_measurement_theta_min 0.80 _cell_measurement_theta_max 28.13 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.5 _exptl_crystal_size_mid 0.4 _exptl_crystal_size_min 0.1 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.356 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 384 _exptl_absorpt_coefficient_mu 0.101 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 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_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4499 _diffrn_reflns_av_R_equivalents 0.1735 _diffrn_reflns_av_sigmaI/netI 0.1252 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 1.18 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3017 _reflns_number_gt 2270 _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^)+(0.0967P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3017 _refine_ls_number_parameters 190 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0948 _refine_ls_R_factor_gt 0.0761 _refine_ls_wR_factor_ref 0.1924 _refine_ls_wR_factor_gt 0.1793 _refine_ls_goodness_of_fit_ref 1.014 _refine_ls_restrained_S_all 1.014 _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 -0.0192(5) 0.3152(3) -0.31786(16) 0.0180(7) Uani 1 1 d . . . H1A H -0.1507 0.3221 -0.3558 0.022 Uiso 1 1 calc R . . H1B H 0.0712 0.4231 -0.3070 0.022 Uiso 1 1 calc R . . C2 C -0.1062(4) 0.2548(3) -0.24416(15) 0.0142(6) Uani 1 1 d . . . H2A H -0.1950 0.3299 -0.2215 0.017 Uiso 1 1 calc R . . H2B H -0.2087 0.1513 -0.2554 0.017 Uiso 1 1 calc R . . C3 C 0.2450(4) 0.1446(3) -0.22139(15) 0.0138(6) Uani 1 1 d . . . H3A H 0.1702 0.0324 -0.2304 0.017 Uiso 1 1 calc R . . H3B H 0.3824 0.1498 -0.1843 0.017 Uiso 1 1 calc R . . C4 C 0.3148(4) 0.2098(3) -0.29727(15) 0.0139(6) Uani 1 1 d . . . H4A H 0.4046 0.3180 -0.2870 0.017 Uiso 1 1 calc R . . H4B H 0.4136 0.1426 -0.3206 0.017 Uiso 1 1 calc R . . C5 C 0.0776(4) 0.2744(3) -0.11211(15) 0.0104(6) Uani 1 1 d . . . C6 C 0.2728(4) 0.2415(3) -0.05608(15) 0.0134(6) Uani 1 1 d . . . H6A H 0.4202 0.2925 -0.0733 0.016 Uiso 1 1 calc R . . H6B H 0.2712 0.1260 -0.0570 0.016 Uiso 1 1 calc R . . C7 C 0.2555(4) 0.3032(3) 0.02691(15) 0.0125(6) Uani 1 1 d . . . H7 H 0.2172 0.4119 0.0249 0.015 Uiso 1 1 calc R . . C8 C 0.0693(4) 0.2006(3) 0.06633(15) 0.0142(6) Uani 1 1 d . . . H8A H 0.1057 0.0929 0.0703 0.017 Uiso 1 1 calc R . . H8B H -0.0792 0.1918 0.0347 0.017 Uiso 1 1 calc R . . C9 C 0.0509(4) 0.2726(3) 0.14746(15) 0.0123(6) Uani 1 1 d . . . H9A H 0.0015 0.3764 0.1430 0.015 Uiso 1 1 calc R . . H9B H -0.0665 0.2024 0.1728 0.015 Uiso 1 1 calc R . . C10 C 0.2795(4) 0.2943(3) 0.19745(15) 0.0121(5) Uani 1 1 d . . . C11 C 0.4723(4) 0.3873(3) 0.15800(16) 0.0133(6) Uani 1 1 d . . . H11A H 0.6193 0.3888 0.1896 0.016 Uiso 1 1 calc R . . H11B H 0.4479 0.4981 0.1546 0.016 Uiso 1 1 calc R . . C12 C 0.4855(4) 0.3152(3) 0.07637(15) 0.0138(6) Uani 1 1 d . . . H12A H 0.5257 0.2084 0.0800 0.017 Uiso 1 1 calc R . . H12B H 0.6070 0.3819 0.0512 0.017 Uiso 1 1 calc R . . C13 C 0.4888(4) 0.2308(3) 0.33624(15) 0.0121(5) Uani 1 1 d . . . C14 C 0.2972(4) 0.1402(3) 0.37678(16) 0.0139(6) Uani 1 1 d . . . H14A H 0.3252 0.0312 0.3840 0.017 Uiso 1 1 calc R . . H14B H 0.1502 0.1333 0.3444 0.017 Uiso 1 1 calc R . . C15 C 0.2825(5) 0.2232(3) 0.45572(16) 0.0163(6) Uani 1 1 d . . . H15A H 0.1659 0.1577 0.4834 0.020 Uiso 1 1 calc R . . H15B H 0.2332 0.3262 0.4478 0.020 Uiso 1 1 calc R . . C16 C 0.5126(4) 0.2510(3) 0.50561(16) 0.0175(7) Uani 1 1 d . . . H16A H 0.4994 0.3129 0.5540 0.021 Uiso 1 1 calc R . . H16B H 0.5509 0.1477 0.5199 0.021 Uiso 1 1 calc R . . C17 C 0.7044(4) 0.3389(3) 0.46350(15) 0.0158(6) Uani 1 1 d . . . H17A H 0.8518 0.3463 0.4958 0.019 Uiso 1 1 calc R . . H17B H 0.6773 0.4479 0.4556 0.019 Uiso 1 1 calc R . . C18 C 0.7189(4) 0.2544(3) 0.38479(15) 0.0133(6) Uani 1 1 d . . . H18A H 0.8368 0.3181 0.3569 0.016 Uiso 1 1 calc R . . H18B H 0.7645 0.1503 0.3929 0.016 Uiso 1 1 calc R . . N1 N 0.0867(4) 0.2373(3) -0.18891(13) 0.0127(5) Uani 1 1 d . . . O1 O 0.1202(3) 0.2146(2) -0.35063(10) 0.0145(3) Uani 1 1 d . . . O2 O -0.0809(3) 0.3333(2) -0.09002(10) 0.0145(3) Uani 1 1 d . . . O3 O 0.2399(3) 0.3711(2) 0.26831(10) 0.0145(3) Uani 1 1 d . . . O4 O 0.4541(3) 0.3871(2) 0.32011(10) 0.0145(3) Uani 1 1 d . . . O5 O 0.3127(3) 0.1371(2) 0.21283(10) 0.0145(3) Uani 1 1 d . . . O6 O 0.5262(3) 0.1519(2) 0.26518(10) 0.0145(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 0.0185(15) 0.0203(16) 0.0126(15) 0.0020(12) -0.0070(12) 0.0002(12) C2 0.0131(14) 0.0132(15) 0.0125(15) -0.0029(11) -0.0063(11) -0.0032(11) C3 0.0164(14) 0.0123(14) 0.0105(14) -0.0008(11) -0.0042(11) -0.0009(11) C4 0.0145(14) 0.0156(14) 0.0080(14) -0.0036(11) -0.0059(11) -0.0032(11) C5 0.0103(13) 0.0070(13) 0.0116(14) -0.0001(10) -0.0042(11) -0.0026(10) C6 0.0130(14) 0.0112(14) 0.0124(15) -0.0053(11) -0.0068(11) -0.0028(11) C7 0.0130(14) 0.0119(14) 0.0099(14) -0.0033(10) -0.0051(11) -0.0015(11) C8 0.0144(14) 0.0129(14) 0.0120(15) -0.0025(11) -0.0081(11) -0.0014(11) C9 0.0106(13) 0.0135(14) 0.0099(14) -0.0017(11) -0.0053(11) -0.0026(11) C10 0.0162(10) 0.0100(10) 0.0074(10) -0.0049(7) -0.0072(8) 0.0001(8) C11 0.0117(13) 0.0123(14) 0.0120(14) -0.0032(10) -0.0066(11) -0.0037(11) C12 0.0128(14) 0.0148(14) 0.0100(14) -0.0023(11) -0.0048(11) -0.0047(11) C13 0.0162(10) 0.0100(10) 0.0074(10) -0.0049(7) -0.0072(8) 0.0001(8) C14 0.0132(14) 0.0110(14) 0.0139(15) -0.0051(11) -0.0082(11) -0.0014(11) C15 0.0155(14) 0.0181(15) 0.0115(15) -0.0041(11) -0.0057(11) -0.0033(12) C16 0.0176(15) 0.0235(16) 0.0084(14) -0.0038(11) -0.0069(11) 0.0004(12) C17 0.0156(14) 0.0183(15) 0.0100(14) -0.0066(11) -0.0093(11) 0.0001(12) C18 0.0122(14) 0.0143(14) 0.0105(14) -0.0031(11) -0.0054(11) -0.0013(11) N1 0.0128(12) 0.0138(12) 0.0094(12) -0.0024(9) -0.0063(9) 0.0010(9) O1 0.0154(5) 0.0166(5) 0.0086(5) -0.0044(3) -0.0087(3) 0.0010(3) O2 0.0154(5) 0.0166(5) 0.0086(5) -0.0044(3) -0.0087(3) 0.0010(3) O3 0.0154(5) 0.0166(5) 0.0086(5) -0.0044(3) -0.0087(3) 0.0010(3) O4 0.0154(5) 0.0166(5) 0.0086(5) -0.0044(3) -0.0087(3) 0.0010(3) O5 0.0154(5) 0.0166(5) 0.0086(5) -0.0044(3) -0.0087(3) 0.0010(3) O6 0.0154(5) 0.0166(5) 0.0086(5) -0.0044(3) -0.0087(3) 0.0010(3) _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 1.430(3) . ? C1 C2 1.503(4) . ? C1 H1A 0.9900 . ? C1 H1B 0.9900 . ? C2 N1 1.464(3) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 N1 1.466(3) . ? C3 C4 1.518(4) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 O1 1.427(3) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 O2 1.226(3) . ? C5 N1 1.365(3) . ? C5 C6 1.523(4) . ? C6 C7 1.530(4) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 C8 1.527(4) . ? C7 C12 1.538(3) . ? C7 H7 1.0000 . ? C8 C9 1.533(4) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 C10 1.529(3) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 O3 1.427(3) . ? C10 O5 1.431(3) . ? C10 C11 1.518(4) . ? C11 C12 1.535(4) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 O4 1.429(3) . ? C13 O6 1.433(3) . ? C13 C14 1.514(4) . ? C13 C18 1.523(3) . ? C14 C15 1.532(4) . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C15 C16 1.533(3) . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C16 C17 1.521(4) . ? C16 H16A 0.9900 . ? C16 H16B 0.9900 . ? C17 C18 1.534(3) . ? C17 H17A 0.9900 . ? C17 H17B 0.9900 . ? C18 H18A 0.9900 . ? C18 H18B 0.9900 . ? O3 O4 1.478(2) . ? O5 O6 1.481(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 O1 C1 C2 111.7(2) . . ? O1 C1 H1A 109.3 . . ? C2 C1 H1A 109.3 . . ? O1 C1 H1B 109.3 . . ? C2 C1 H1B 109.3 . . ? H1A C1 H1B 107.9 . . ? N1 C2 C1 109.7(2) . . ? N1 C2 H2A 109.7 . . ? C1 C2 H2A 109.7 . . ? N1 C2 H2B 109.7 . . ? C1 C2 H2B 109.7 . . ? H2A C2 H2B 108.2 . . ? N1 C3 C4 109.8(2) . . ? N1 C3 H3A 109.7 . . ? C4 C3 H3A 109.7 . . ? N1 C3 H3B 109.7 . . ? C4 C3 H3B 109.7 . . ? H3A C3 H3B 108.2 . . ? O1 C4 C3 111.5(2) . . ? O1 C4 H4A 109.3 . . ? C3 C4 H4A 109.3 . . ? O1 C4 H4B 109.3 . . ? C3 C4 H4B 109.3 . . ? H4A C4 H4B 108.0 . . ? O2 C5 N1 120.8(2) . . ? O2 C5 C6 122.0(2) . . ? N1 C5 C6 117.2(2) . . ? C5 C6 C7 112.1(2) . . ? C5 C6 H6A 109.2 . . ? C7 C6 H6A 109.2 . . ? C5 C6 H6B 109.2 . . ? C7 C6 H6B 109.2 . . ? H6A C6 H6B 107.9 . . ? C8 C7 C6 112.8(2) . . ? C8 C7 C12 109.1(2) . . ? C6 C7 C12 110.8(2) . . ? C8 C7 H7 108.0 . . ? C6 C7 H7 108.0 . . ? C12 C7 H7 108.0 . . ? C7 C8 C9 110.6(2) . . ? C7 C8 H8A 109.5 . . ? C9 C8 H8A 109.5 . . ? C7 C8 H8B 109.5 . . ? C9 C8 H8B 109.5 . . ? H8A C8 H8B 108.1 . . ? C10 C9 C8 111.3(2) . . ? C10 C9 H9A 109.4 . . ? C8 C9 H9A 109.4 . . ? C10 C9 H9B 109.4 . . ? C8 C9 H9B 109.4 . . ? H9A C9 H9B 108.0 . . ? O3 C10 O5 108.1(2) . . ? O3 C10 C11 113.0(2) . . ? O5 C10 C11 113.5(2) . . ? O3 C10 C9 104.8(2) . . ? O5 C10 C9 104.8(2) . . ? C11 C10 C9 112.0(2) . . ? C10 C11 C12 111.6(2) . . ? C10 C11 H11A 109.3 . . ? C12 C11 H11A 109.3 . . ? C10 C11 H11B 109.3 . . ? C12 C11 H11B 109.3 . . ? H11A C11 H11B 108.0 . . ? C11 C12 C7 110.7(2) . . ? C11 C12 H12A 109.5 . . ? C7 C12 H12A 109.5 . . ? C11 C12 H12B 109.5 . . ? C7 C12 H12B 109.5 . . ? H12A C12 H12B 108.1 . . ? O4 C13 O6 108.1(2) . . ? O4 C13 C14 112.8(2) . . ? O6 C13 C14 113.3(2) . . ? O4 C13 C18 104.7(2) . . ? O6 C13 C18 104.6(2) . . ? C14 C13 C18 112.6(2) . . ? C13 C14 C15 110.3(2) . . ? C13 C14 H14A 109.6 . . ? C15 C14 H14A 109.6 . . ? C13 C14 H14B 109.6 . . ? C15 C14 H14B 109.6 . . ? H14A C14 H14B 108.1 . . ? C14 C15 C16 111.8(2) . . ? C14 C15 H15A 109.3 . . ? C16 C15 H15A 109.3 . . ? C14 C15 H15B 109.3 . . ? C16 C15 H15B 109.3 . . ? H15A C15 H15B 107.9 . . ? C17 C16 C15 111.9(2) . . ? C17 C16 H16A 109.2 . . ? C15 C16 H16A 109.2 . . ? C17 C16 H16B 109.2 . . ? C15 C16 H16B 109.2 . . ? H16A C16 H16B 107.9 . . ? C16 C17 C18 111.2(2) . . ? C16 C17 H17A 109.4 . . ? C18 C17 H17A 109.4 . . ? C16 C17 H17B 109.4 . . ? C18 C17 H17B 109.4 . . ? H17A C17 H17B 108.0 . . ? C13 C18 C17 110.4(2) . . ? C13 C18 H18A 109.6 . . ? C17 C18 H18A 109.6 . . ? C13 C18 H18B 109.6 . . ? C17 C18 H18B 109.6 . . ? H18A C18 H18B 108.1 . . ? C5 N1 C2 119.0(2) . . ? C5 N1 C3 125.9(2) . . ? C2 N1 C3 113.4(2) . . ? C4 O1 C1 109.31(19) . . ? C10 O3 O4 106.65(17) . . ? C13 O4 O3 107.16(16) . . ? C10 O5 O6 107.01(16) . . ? C13 O6 O5 107.15(17) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 C1 C2 N1 56.4(3) . . . . ? N1 C3 C4 O1 -55.4(3) . . . . ? O2 C5 C6 C7 -4.9(3) . . . . ? N1 C5 C6 C7 174.3(2) . . . . ? C5 C6 C7 C8 74.7(3) . . . . ? C5 C6 C7 C12 -162.7(2) . . . . ? C6 C7 C8 C9 -176.9(2) . . . . ? C12 C7 C8 C9 59.5(3) . . . . ? C7 C8 C9 C10 -57.0(3) . . . . ? C8 C9 C10 O3 176.2(2) . . . . ? C8 C9 C10 O5 -70.1(3) . . . . ? C8 C9 C10 C11 53.4(3) . . . . ? O3 C10 C11 C12 -171.0(2) . . . . ? O5 C10 C11 C12 65.5(3) . . . . ? C9 C10 C11 C12 -52.9(3) . . . . ? C10 C11 C12 C7 56.0(3) . . . . ? C8 C7 C12 C11 -59.0(3) . . . . ? C6 C7 C12 C11 176.2(2) . . . . ? O4 C13 C14 C15 -62.3(3) . . . . ? O6 C13 C14 C15 174.5(2) . . . . ? C18 C13 C14 C15 56.0(3) . . . . ? C13 C14 C15 C16 -54.0(3) . . . . ? C14 C15 C16 C17 54.0(3) . . . . ? C15 C16 C17 C18 -54.2(3) . . . . ? O4 C13 C18 C17 66.3(3) . . . . ? O6 C13 C18 C17 179.9(2) . . . . ? C14 C13 C18 C17 -56.7(3) . . . . ? C16 C17 C18 C13 54.9(3) . . . . ? O2 C5 N1 C2 -5.6(4) . . . . ? C6 C5 N1 C2 175.1(2) . . . . ? O2 C5 N1 C3 -169.7(2) . . . . ? C6 C5 N1 C3 11.0(4) . . . . ? C1 C2 N1 C5 142.3(2) . . . . ? C1 C2 N1 C3 -51.7(3) . . . . ? C4 C3 N1 C5 -143.9(3) . . . . ? C4 C3 N1 C2 51.2(3) . . . . ? C3 C4 O1 C1 60.6(3) . . . . ? C2 C1 O1 C4 -61.3(3) . . . . ? O5 C10 O3 O4 65.7(2) . . . . ? C11 C10 O3 O4 -60.7(3) . . . . ? C9 C10 O3 O4 177.14(18) . . . . ? O6 C13 O4 O3 65.0(2) . . . . ? C14 C13 O4 O3 -61.1(2) . . . . ? C18 C13 O4 O3 176.12(17) . . . . ? C10 O3 O4 C13 -64.9(2) . . . . ? O3 C10 O5 O6 -65.3(2) . . . . ? C11 C10 O5 O6 60.8(2) . . . . ? C9 C10 O5 O6 -176.70(17) . . . . ? O4 C13 O6 O5 -64.3(2) . . . . ? C14 C13 O6 O5 61.5(3) . . . . ? C18 C13 O6 O5 -175.51(18) . . . . ? C10 O5 O6 C13 63.7(2) . . . . ? _diffrn_measured_fraction_theta_max 0.984 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.984 _refine_diff_density_max 0.495 _refine_diff_density_min -0.448 _refine_diff_density_rms 0.083 data_rka216 _database_code_depnum_ccdc_archive 'CCDC 616880' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety (C22H33NO6) _chemical_formula_sum 'C22 H33 N O6' _chemical_formula_weight 407.49 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 Monoclinic _symmetry_space_group_name_H-M P21/n _symmetry_space_group_name_Hall -P2yn 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 6.2610(6) _cell_length_b 37.479(3) _cell_length_c 8.6291(8) _cell_angle_alpha 90.00 _cell_angle_beta 90.841(2) _cell_angle_gamma 90.00 _cell_volume 2024.7(3) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 12387 _cell_measurement_theta_min 0.90 _cell_measurement_theta_max 28.12 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.2 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.337 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 880 _exptl_absorpt_coefficient_mu 0.096 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 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_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10349 _diffrn_reflns_av_R_equivalents 0.1699 _diffrn_reflns_av_sigmaI/netI 0.1027 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -42 _diffrn_reflns_limit_k_max 44 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 7 _diffrn_reflns_theta_min 1.09 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3562 _reflns_number_gt 3011 _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^)+(0.1172P)^2^+0.4706P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3562 _refine_ls_number_parameters 184 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0779 _refine_ls_R_factor_gt 0.0707 _refine_ls_wR_factor_ref 0.1943 _refine_ls_wR_factor_gt 0.1875 _refine_ls_goodness_of_fit_ref 1.056 _refine_ls_restrained_S_all 1.056 _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 0.9308(3) -0.04547(6) 0.3066(2) 0.0168(5) Uani 1 1 d . . . C2 C 0.7424(3) -0.01969(6) 0.3102(2) 0.0174(5) Uani 1 1 d . . . H2A H 0.7276 -0.0105 0.4171 0.021 Uiso 1 1 calc R . . H2B H 0.6101 -0.0329 0.2832 0.021 Uiso 1 1 calc R . . C3 C 0.7643(3) 0.01186(5) 0.1996(2) 0.0138(3) Uani 1 1 d . . . H3 H 0.8109 0.0025 0.0970 0.017 Uiso 1 1 calc R . . C4 C 0.9292(3) 0.03944(6) 0.2553(2) 0.0164(3) Uani 1 1 d . . . H4A H 0.8871 0.0488 0.3578 0.020 Uiso 1 1 calc R . . H4B H 1.0703 0.0278 0.2676 0.020 Uiso 1 1 calc R . . C5 C 0.9464(3) 0.07026(6) 0.1409(2) 0.0164(3) Uani 1 1 d . . . H5A H 1.0480 0.0882 0.1826 0.020 Uiso 1 1 calc R . . H5B H 1.0032 0.0613 0.0418 0.020 Uiso 1 1 calc R . . C6 C 0.7303(3) 0.08787(5) 0.1111(2) 0.0138(3) Uani 1 1 d . . . C7 C 0.5603(3) 0.06118(6) 0.0614(2) 0.0164(3) Uani 1 1 d . . . H7A H 0.5941 0.0518 -0.0426 0.020 Uiso 1 1 calc R . . H7B H 0.4200 0.0733 0.0543 0.020 Uiso 1 1 calc R . . C8 C 0.5472(3) 0.03029(6) 0.1761(2) 0.0164(3) Uani 1 1 d . . . H8A H 0.4416 0.0126 0.1374 0.020 Uiso 1 1 calc R . . H8B H 0.4972 0.0394 0.2770 0.020 Uiso 1 1 calc R . . C9 C 1.0766(3) -0.10434(6) 0.3723(3) 0.0182(5) Uani 1 1 d . . . H9A H 1.1375 -0.1068 0.4783 0.022 Uiso 1 1 calc R . . H9B H 1.1915 -0.0963 0.3028 0.022 Uiso 1 1 calc R . . C10 C 0.9896(3) -0.14002(6) 0.3175(3) 0.0218(5) Uani 1 1 d . . . H10A H 0.9427 -0.1380 0.2078 0.026 Uiso 1 1 calc R . . H10B H 1.1048 -0.1581 0.3233 0.026 Uiso 1 1 calc R . . C11 C 0.6448(3) -0.12614(6) 0.3992(3) 0.0212(5) Uani 1 1 d . . . H11A H 0.5231 -0.1346 0.4613 0.025 Uiso 1 1 calc R . . H11B H 0.5952 -0.1238 0.2902 0.025 Uiso 1 1 calc R . . C12 C 0.7176(3) -0.09004(6) 0.4587(2) 0.0183(5) Uani 1 1 d . . . H12A H 0.6002 -0.0725 0.4467 0.022 Uiso 1 1 calc R . . H12B H 0.7555 -0.0918 0.5702 0.022 Uiso 1 1 calc R . . C13 C 0.5298(3) 0.15279(5) 0.1112(2) 0.0138(3) Uani 1 1 d . . . C14 C 0.3192(3) 0.17289(6) 0.0857(2) 0.0166(3) Uani 1 1 d . . . H14 H 0.2029 0.1557 0.0574 0.020 Uiso 1 1 calc R . . C15 C 0.2630(3) 0.19253(6) 0.2361(2) 0.0166(3) Uani 1 1 d . . . H15A H 0.2447 0.1750 0.3208 0.020 Uiso 1 1 calc R . . H15B H 0.1266 0.2056 0.2215 0.020 Uiso 1 1 calc R . . C16 C 0.4422(3) 0.21902(6) 0.2800(2) 0.0166(3) Uani 1 1 d . . . H16 H 0.4042 0.2318 0.3775 0.020 Uiso 1 1 calc R . . C17 C 0.6511(3) 0.19811(6) 0.3059(2) 0.0166(3) Uani 1 1 d . . . H17A H 0.7673 0.2148 0.3361 0.020 Uiso 1 1 calc R . . H17B H 0.6330 0.1807 0.3909 0.020 Uiso 1 1 calc R . . C18 C 0.7105(3) 0.17849(6) 0.1570(3) 0.0166(3) Uani 1 1 d . . . H18 H 0.8466 0.1650 0.1734 0.020 Uiso 1 1 calc R . . C19 C 0.7364(3) 0.20558(6) 0.0253(2) 0.0166(3) Uani 1 1 d . . . H19A H 0.7749 0.1929 -0.0711 0.020 Uiso 1 1 calc R . . H19B H 0.8531 0.2224 0.0519 0.020 Uiso 1 1 calc R . . C20 C 0.5270(3) 0.22639(6) -0.0011(2) 0.0166(3) Uani 1 1 d . . . H20 H 0.5462 0.2441 -0.0864 0.020 Uiso 1 1 calc R . . C21 C 0.3486(3) 0.20013(6) -0.0462(2) 0.0166(3) Uani 1 1 d . . . H21A H 0.3862 0.1875 -0.1429 0.020 Uiso 1 1 calc R . . H21B H 0.2135 0.2133 -0.0649 0.020 Uiso 1 1 calc R . . C22 C 0.4696(3) 0.24604(6) 0.1490(2) 0.0166(3) Uani 1 1 d . . . H22A H 0.5843 0.2632 0.1769 0.020 Uiso 1 1 calc R . . H22B H 0.3354 0.2596 0.1331 0.020 Uiso 1 1 calc R . . N1 N 0.9032(3) -0.07809(5) 0.3718(2) 0.0173(4) Uani 1 1 d . . . O1 O 1.0994(2) -0.03738(4) 0.24406(18) 0.0237(4) Uani 1 1 d . . . O2 O 0.8141(2) -0.15162(4) 0.40838(18) 0.0248(4) Uani 1 1 d . . . O3 O 0.7706(2) 0.11412(4) -0.00479(16) 0.0157(4) Uani 1 1 d . . . O4 O 0.5698(2) 0.13428(4) -0.02970(16) 0.0158(4) Uani 1 1 d . . . O5 O 0.48514(19) 0.12655(4) 0.22652(16) 0.0138(4) Uani 1 1 d . . . O6 O 0.6835(2) 0.10595(4) 0.25284(16) 0.0142(4) 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 0.0089(10) 0.0156(11) 0.0259(11) -0.0011(8) -0.0003(8) 0.0000(8) C2 0.0067(9) 0.0154(11) 0.0300(11) 0.0012(9) 0.0001(8) -0.0004(8) C3 0.0050(6) 0.0124(6) 0.0240(6) -0.0005(5) 0.0012(5) 0.0000(5) C4 0.0047(5) 0.0143(6) 0.0302(6) -0.0023(4) -0.0015(4) -0.0002(4) C5 0.0047(5) 0.0143(6) 0.0302(6) -0.0023(4) -0.0015(4) -0.0002(4) C6 0.0050(6) 0.0124(6) 0.0240(6) -0.0005(5) 0.0012(5) 0.0000(5) C7 0.0047(5) 0.0143(6) 0.0302(6) -0.0023(4) -0.0015(4) -0.0002(4) C8 0.0047(5) 0.0143(6) 0.0302(6) -0.0023(4) -0.0015(4) -0.0002(4) C9 0.0108(10) 0.0147(11) 0.0290(11) 0.0000(9) -0.0017(8) 0.0035(8) C10 0.0187(11) 0.0155(11) 0.0312(12) -0.0009(9) 0.0052(9) 0.0012(9) C11 0.0140(10) 0.0203(12) 0.0294(12) 0.0012(9) 0.0011(9) -0.0053(9) C12 0.0115(10) 0.0157(11) 0.0280(11) 0.0018(9) 0.0030(9) -0.0005(8) C13 0.0050(6) 0.0124(6) 0.0240(6) -0.0005(5) 0.0012(5) 0.0000(5) C14 0.0033(4) 0.0150(5) 0.0315(5) 0.0005(3) -0.0013(3) -0.0001(3) C15 0.0033(4) 0.0150(5) 0.0315(5) 0.0005(3) -0.0013(3) -0.0001(3) C16 0.0033(4) 0.0150(5) 0.0315(5) 0.0005(3) -0.0013(3) -0.0001(3) C17 0.0033(4) 0.0150(5) 0.0315(5) 0.0005(3) -0.0013(3) -0.0001(3) C18 0.0033(4) 0.0150(5) 0.0315(5) 0.0005(3) -0.0013(3) -0.0001(3) C19 0.0033(4) 0.0150(5) 0.0315(5) 0.0005(3) -0.0013(3) -0.0001(3) C20 0.0033(4) 0.0150(5) 0.0315(5) 0.0005(3) -0.0013(3) -0.0001(3) C21 0.0033(4) 0.0150(5) 0.0315(5) 0.0005(3) -0.0013(3) -0.0001(3) C22 0.0033(4) 0.0150(5) 0.0315(5) 0.0005(3) -0.0013(3) -0.0001(3) N1 0.0084(8) 0.0133(9) 0.0302(10) 0.0020(7) 0.0011(7) 0.0007(7) O1 0.0110(7) 0.0138(8) 0.0464(10) 0.0042(7) 0.0095(7) 0.0004(6) O2 0.0230(8) 0.0158(8) 0.0359(9) 0.0023(7) 0.0062(7) -0.0017(6) O3 0.0037(6) 0.0149(8) 0.0286(8) 0.0028(6) 0.0028(6) 0.0050(6) O4 0.0049(7) 0.0171(8) 0.0253(8) -0.0003(6) -0.0013(6) 0.0049(5) O5 0.0013(6) 0.0118(7) 0.0284(8) 0.0023(6) 0.0007(6) 0.0028(5) O6 0.0030(6) 0.0134(8) 0.0262(8) -0.0010(6) -0.0024(6) 0.0044(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 O1 1.231(3) . ? C1 N1 1.358(3) . ? C1 C2 1.525(3) . ? C2 C3 1.527(3) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C4 1.533(3) . ? C3 C8 1.535(3) . ? C3 H3 1.0000 . ? C4 C5 1.524(3) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 C6 1.524(3) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 O3 1.428(2) . ? C6 O6 1.432(2) . ? C6 C7 1.518(3) . ? C7 C8 1.526(3) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 N1 1.465(3) . ? C9 C10 1.517(3) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 O2 1.427(3) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 O2 1.429(3) . ? C11 C12 1.515(3) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 N1 1.463(3) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 O4 1.425(2) . ? C13 O5 1.430(2) . ? C13 C14 1.532(3) . ? C13 C18 1.533(3) . ? C14 C15 1.537(3) . ? C14 C21 1.542(3) . ? C14 H14 1.0000 . ? C15 C16 1.541(3) . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C16 C22 1.529(3) . ? C16 C17 1.539(3) . ? C16 H16 1.0000 . ? C17 C18 1.531(3) . ? C17 H17A 0.9900 . ? C17 H17B 0.9900 . ? C18 C19 1.534(3) . ? C18 H18 1.0000 . ? C19 C20 1.540(3) . ? C19 H19A 0.9900 . ? C19 H19B 0.9900 . ? C20 C21 1.535(3) . ? C20 C22 1.537(3) . ? C20 H20 1.0000 . ? C21 H21A 0.9900 . ? C21 H21B 0.9900 . ? C22 H22A 0.9900 . ? C22 H22B 0.9900 . ? O3 O4 1.4796(18) . ? O5 O6 1.4771(17) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 C1 N1 121.25(19) . . ? O1 C1 C2 121.42(19) . . ? N1 C1 C2 117.31(18) . . ? C1 C2 C3 113.67(17) . . ? C1 C2 H2A 108.8 . . ? C3 C2 H2A 108.8 . . ? C1 C2 H2B 108.8 . . ? C3 C2 H2B 108.8 . . ? H2A C2 H2B 107.7 . . ? C2 C3 C4 113.07(16) . . ? C2 C3 C8 110.10(17) . . ? C4 C3 C8 109.20(16) . . ? C2 C3 H3 108.1 . . ? C4 C3 H3 108.1 . . ? C8 C3 H3 108.1 . . ? C5 C4 C3 111.18(16) . . ? C5 C4 H4A 109.4 . . ? C3 C4 H4A 109.4 . . ? C5 C4 H4B 109.4 . . ? C3 C4 H4B 109.4 . . ? H4A C4 H4B 108.0 . . ? C6 C5 C4 111.48(17) . . ? C6 C5 H5A 109.3 . . ? C4 C5 H5A 109.3 . . ? C6 C5 H5B 109.3 . . ? C4 C5 H5B 109.3 . . ? H5A C5 H5B 108.0 . . ? O3 C6 O6 108.23(15) . . ? O3 C6 C7 112.71(15) . . ? O6 C6 C7 113.69(16) . . ? O3 C6 C5 104.54(15) . . ? O6 C6 C5 104.67(15) . . ? C7 C6 C5 112.30(17) . . ? C6 C7 C8 111.12(16) . . ? C6 C7 H7A 109.4 . . ? C8 C7 H7A 109.4 . . ? C6 C7 H7B 109.4 . . ? C8 C7 H7B 109.4 . . ? H7A C7 H7B 108.0 . . ? C7 C8 C3 111.79(16) . . ? C7 C8 H8A 109.3 . . ? C3 C8 H8A 109.3 . . ? C7 C8 H8B 109.3 . . ? C3 C8 H8B 109.3 . . ? H8A C8 H8B 107.9 . . ? N1 C9 C10 109.17(16) . . ? N1 C9 H9A 109.8 . . ? C10 C9 H9A 109.8 . . ? N1 C9 H9B 109.8 . . ? C10 C9 H9B 109.8 . . ? H9A C9 H9B 108.3 . . ? O2 C10 C9 111.90(18) . . ? O2 C10 H10A 109.2 . . ? C9 C10 H10A 109.2 . . ? O2 C10 H10B 109.2 . . ? C9 C10 H10B 109.2 . . ? H10A C10 H10B 107.9 . . ? O2 C11 C12 111.04(17) . . ? O2 C11 H11A 109.4 . . ? C12 C11 H11A 109.4 . . ? O2 C11 H11B 109.4 . . ? C12 C11 H11B 109.4 . . ? H11A C11 H11B 108.0 . . ? N1 C12 C11 109.70(18) . . ? N1 C12 H12A 109.7 . . ? C11 C12 H12A 109.7 . . ? N1 C12 H12B 109.7 . . ? C11 C12 H12B 109.7 . . ? H12A C12 H12B 108.2 . . ? O4 C13 O5 107.31(16) . . ? O4 C13 C14 106.18(15) . . ? O5 C13 C14 105.16(15) . . ? O4 C13 C18 112.79(16) . . ? O5 C13 C18 113.82(16) . . ? C14 C13 C18 111.01(17) . . ? C13 C14 C15 108.76(15) . . ? C13 C14 C21 108.64(16) . . ? C15 C14 C21 109.73(17) . . ? C13 C14 H14 109.9 . . ? C15 C14 H14 109.9 . . ? C21 C14 H14 109.9 . . ? C14 C15 C16 109.95(16) . . ? C14 C15 H15A 109.7 . . ? C16 C15 H15A 109.7 . . ? C14 C15 H15B 109.7 . . ? C16 C15 H15B 109.7 . . ? H15A C15 H15B 108.2 . . ? C22 C16 C17 109.89(16) . . ? C22 C16 C15 109.52(16) . . ? C17 C16 C15 108.78(17) . . ? C22 C16 H16 109.5 . . ? C17 C16 H16 109.5 . . ? C15 C16 H16 109.5 . . ? C18 C17 C16 109.82(16) . . ? C18 C17 H17A 109.7 . . ? C16 C17 H17A 109.7 . . ? C18 C17 H17B 109.7 . . ? C16 C17 H17B 109.7 . . ? H17A C17 H17B 108.2 . . ? C17 C18 C13 109.30(16) . . ? C17 C18 C19 109.47(17) . . ? C13 C18 C19 108.09(16) . . ? C17 C18 H18 110.0 . . ? C13 C18 H18 110.0 . . ? C19 C18 H18 110.0 . . ? C18 C19 C20 110.25(16) . . ? C18 C19 H19A 109.6 . . ? C20 C19 H19A 109.6 . . ? C18 C19 H19B 109.6 . . ? C20 C19 H19B 109.6 . . ? H19A C19 H19B 108.1 . . ? C21 C20 C22 110.06(17) . . ? C21 C20 C19 109.11(17) . . ? C22 C20 C19 109.08(16) . . ? C21 C20 H20 109.5 . . ? C22 C20 H20 109.5 . . ? C19 C20 H20 109.5 . . ? C20 C21 C14 109.37(16) . . ? C20 C21 H21A 109.8 . . ? C14 C21 H21A 109.8 . . ? C20 C21 H21B 109.8 . . ? C14 C21 H21B 109.8 . . ? H21A C21 H21B 108.2 . . ? C16 C22 C20 109.62(17) . . ? C16 C22 H22A 109.7 . . ? C20 C22 H22A 109.7 . . ? C16 C22 H22B 109.7 . . ? C20 C22 H22B 109.7 . . ? H22A C22 H22B 108.2 . . ? C1 N1 C12 126.52(18) . . ? C1 N1 C9 120.47(18) . . ? C12 N1 C9 112.77(17) . . ? C10 O2 C11 110.04(17) . . ? C6 O3 O4 107.17(13) . . ? C13 O4 O3 106.51(13) . . ? C13 O5 O6 107.10(13) . . ? C6 O6 O5 107.35(12) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 C1 C2 C3 13.6(3) . . . . ? N1 C1 C2 C3 -164.71(18) . . . . ? C1 C2 C3 C4 -73.4(2) . . . . ? C1 C2 C3 C8 164.19(17) . . . . ? C2 C3 C4 C5 179.64(16) . . . . ? C8 C3 C4 C5 -57.4(2) . . . . ? C3 C4 C5 C6 56.0(2) . . . . ? C4 C5 C6 O3 -176.08(15) . . . . ? C4 C5 C6 O6 70.2(2) . . . . ? C4 C5 C6 C7 -53.6(2) . . . . ? O3 C6 C7 C8 170.81(16) . . . . ? O6 C6 C7 C8 -65.6(2) . . . . ? C5 C6 C7 C8 53.0(2) . . . . ? C6 C7 C8 C3 -55.5(2) . . . . ? C2 C3 C8 C7 -177.87(16) . . . . ? C4 C3 C8 C7 57.4(2) . . . . ? N1 C9 C10 O2 -55.8(2) . . . . ? O2 C11 C12 N1 56.7(2) . . . . ? O4 C13 C14 C15 178.15(15) . . . . ? O5 C13 C14 C15 64.61(19) . . . . ? C18 C13 C14 C15 -58.9(2) . . . . ? O4 C13 C14 C21 -62.5(2) . . . . ? O5 C13 C14 C21 -176.00(15) . . . . ? C18 C13 C14 C21 60.5(2) . . . . ? C13 C14 C15 C16 59.6(2) . . . . ? C21 C14 C15 C16 -59.09(19) . . . . ? C14 C15 C16 C22 59.4(2) . . . . ? C14 C15 C16 C17 -60.7(2) . . . . ? C22 C16 C17 C18 -59.5(2) . . . . ? C15 C16 C17 C18 60.4(2) . . . . ? C16 C17 C18 C13 -59.4(2) . . . . ? C16 C17 C18 C19 58.8(2) . . . . ? O4 C13 C18 C17 178.06(15) . . . . ? O5 C13 C18 C17 -59.4(2) . . . . ? C14 C13 C18 C17 59.0(2) . . . . ? O4 C13 C18 C19 59.0(2) . . . . ? O5 C13 C18 C19 -178.45(15) . . . . ? C14 C13 C18 C19 -60.0(2) . . . . ? C17 C18 C19 C20 -59.3(2) . . . . ? C13 C18 C19 C20 59.6(2) . . . . ? C18 C19 C20 C21 -60.7(2) . . . . ? C18 C19 C20 C22 59.6(2) . . . . ? C22 C20 C21 C14 -59.4(2) . . . . ? C19 C20 C21 C14 60.2(2) . . . . ? C13 C14 C21 C20 -59.9(2) . . . . ? C15 C14 C21 C20 58.9(2) . . . . ? C17 C16 C22 C20 59.9(2) . . . . ? C15 C16 C22 C20 -59.6(2) . . . . ? C21 C20 C22 C16 60.1(2) . . . . ? C19 C20 C22 C16 -59.6(2) . . . . ? O1 C1 N1 C12 175.35(19) . . . . ? C2 C1 N1 C12 -6.3(3) . . . . ? O1 C1 N1 C9 1.4(3) . . . . ? C2 C1 N1 C9 179.78(17) . . . . ? C11 C12 N1 C1 131.6(2) . . . . ? C11 C12 N1 C9 -54.0(2) . . . . ? C10 C9 N1 C1 -132.1(2) . . . . ? C10 C9 N1 C12 53.2(2) . . . . ? C9 C10 O2 C11 59.9(2) . . . . ? C12 C11 O2 C10 -59.9(2) . . . . ? O6 C6 O3 O4 -64.27(16) . . . . ? C7 C6 O3 O4 62.34(19) . . . . ? C5 C6 O3 O4 -175.42(13) . . . . ? O5 C13 O4 O3 -66.67(16) . . . . ? C14 C13 O4 O3 -178.73(13) . . . . ? C18 C13 O4 O3 59.48(19) . . . . ? C6 O3 O4 C13 65.41(17) . . . . ? O4 C13 O5 O6 66.16(16) . . . . ? C14 C13 O5 O6 178.92(13) . . . . ? C18 C13 O5 O6 -59.36(19) . . . . ? O3 C6 O6 O5 63.51(16) . . . . ? C7 C6 O6 O5 -62.53(19) . . . . ? C5 C6 O6 O5 174.57(14) . . . . ? C13 O5 O6 C6 -63.91(17) . . . . ? 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 C4 H4B O1 0.99 2.46 3.072(3) 119.8 . C7 H7B O5 0.99 2.52 2.877(3) 101.1 . C9 H9A O6 0.99 2.56 3.547(2) 173.3 3_756 C9 H9B O1 0.99 2.34 2.747(3) 103.8 . C11 H11B O4 0.99 2.49 3.455(3) 164.5 3_655 C15 H15A O2 0.99 2.53 3.470(3) 158.8 3_656 _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.529 _refine_diff_density_min -0.427 _refine_diff_density_rms 0.092