# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_cambridge 0177 _journal_year ? _journal_volume ? _journal_page_first ? _publ_author_name 'Jie Wu' _publ_contact_author_name 'Jie Wu' _publ_contact_author_email jie_wu@fudan.edu.cn data_a20911a _database_code_depnum_ccdc_archive 'CCDC 901570' #TrackingRef 'a20911a.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C23 H20 N2 O5' _chemical_formula_weight 404.41 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 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 8.013(12) _cell_length_b 9.542(14) _cell_length_c 14.04(2) _cell_angle_alpha 93.728(18) _cell_angle_beta 104.831(19) _cell_angle_gamma 97.695(19) _cell_volume 1023(3) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 894 _cell_measurement_theta_min 2.764 _cell_measurement_theta_max 26.954 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.42 _exptl_crystal_size_mid 0.36 _exptl_crystal_size_min 0.28 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.313 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 424 _exptl_absorpt_coefficient_mu 0.094 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9618 _exptl_absorpt_correction_T_max 0.9743 _exptl_absorpt_process_details sadabs _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 '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_% 5.07 _diffrn_reflns_number 4247 _diffrn_reflns_av_R_equivalents 0.0435 _diffrn_reflns_av_sigmaI/netI 0.0374 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.51 _diffrn_reflns_theta_max 25.01 _reflns_number_total 3517 _reflns_number_gt 2762 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _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^)+(0.1347P)^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 SHELXL _refine_ls_extinction_coef 0.40(2) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3517 _refine_ls_number_parameters 275 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0742 _refine_ls_R_factor_gt 0.0644 _refine_ls_wR_factor_ref 0.1798 _refine_ls_wR_factor_gt 0.1692 _refine_ls_goodness_of_fit_ref 1.025 _refine_ls_restrained_S_all 1.025 _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 N1 N 0.50355(19) 0.13356(15) 0.20650(10) 0.0348(4) Uani 1 1 d . . . N2 N 0.5483(2) 0.01156(16) 0.24450(11) 0.0422(4) Uani 1 1 d . . . O1 O 1.0800(2) 0.1838(3) 0.53679(12) 0.0873(7) Uani 1 1 d . . . O2 O 1.0819(2) 0.18286(18) 0.37981(11) 0.0631(5) Uani 1 1 d . . . O3 O 0.8464(3) 0.4428(2) 0.56165(17) 0.1076(9) Uani 1 1 d . . . O4 O 0.6955(2) 0.22943(18) 0.53702(12) 0.0712(6) Uani 1 1 d . . . O5 O -0.00822(19) -0.38203(15) -0.09044(11) 0.0549(4) Uani 1 1 d . . . C1 C 0.6769(2) 0.0574(2) 0.32487(14) 0.0426(5) Uani 1 1 d . . . H1 H 0.7335 -0.0031 0.3669 0.051 Uiso 1 1 calc R . . C2 C 0.7199(2) 0.20507(19) 0.34084(12) 0.0365(5) Uani 1 1 d . . . C3 C 0.6060(2) 0.25399(18) 0.26304(12) 0.0341(4) Uani 1 1 d . . . C4 C 0.5792(2) 0.39132(19) 0.22875(13) 0.0365(4) Uani 1 1 d . . . C5 C 0.6707(3) 0.5209(2) 0.28072(15) 0.0475(5) Uani 1 1 d . . . H5 H 0.7505 0.5214 0.3419 0.057 Uiso 1 1 calc R . . C6 C 0.6435(3) 0.6477(2) 0.24188(17) 0.0538(6) Uani 1 1 d . . . H6 H 0.7080 0.7327 0.2760 0.065 Uiso 1 1 calc R . . C7 C 0.5210(3) 0.6494(2) 0.15241(17) 0.0538(6) Uani 1 1 d . . . H7 H 0.5021 0.7354 0.1272 0.065 Uiso 1 1 calc R . . C8 C 0.4274(3) 0.5242(2) 0.10092(16) 0.0492(5) Uani 1 1 d . . . H8 H 0.3444 0.5261 0.0413 0.059 Uiso 1 1 calc R . . C9 C 0.4556(2) 0.39285(19) 0.13729(14) 0.0394(5) Uani 1 1 d . . . C10 C 0.3596(2) 0.2616(2) 0.08393(14) 0.0409(5) Uani 1 1 d . . . H10 H 0.2793 0.2648 0.0235 0.049 Uiso 1 1 calc R . . C11 C 0.3793(2) 0.13380(19) 0.11656(13) 0.0355(4) Uani 1 1 d . . . C12 C 0.2799(2) -0.00272(19) 0.06321(13) 0.0367(5) Uani 1 1 d . . . C13 C 0.2544(3) -0.0264(2) -0.03882(14) 0.0438(5) Uani 1 1 d . . . H13 H 0.3035 0.0432 -0.0713 0.053 Uiso 1 1 calc R . . C14 C 0.1585(3) -0.1496(2) -0.09286(14) 0.0460(5) Uani 1 1 d . . . H14 H 0.1423 -0.1623 -0.1610 0.055 Uiso 1 1 calc R . . C15 C 0.0865(2) -0.2543(2) -0.04542(14) 0.0409(5) Uani 1 1 d . . . C16 C 0.1072(3) -0.2319(2) 0.05573(15) 0.0468(5) Uani 1 1 d . . . H16 H 0.0563 -0.3011 0.0878 0.056 Uiso 1 1 calc R . . C17 C 0.2023(3) -0.1081(2) 0.10900(14) 0.0443(5) Uani 1 1 d . . . H17 H 0.2149 -0.0946 0.1768 0.053 Uiso 1 1 calc R . . C18 C 0.8622(2) 0.28863(19) 0.42464(12) 0.0389(5) Uani 1 1 d . . . H18 H 0.9031 0.3769 0.3998 0.047 Uiso 1 1 calc R . . C19 C 1.0188(3) 0.2119(2) 0.45565(14) 0.0460(5) Uani 1 1 d . . . C20 C 1.2345(4) 0.1131(4) 0.3970(3) 0.0960(10) Uani 1 1 d . . . H20A H 1.3311 0.1734 0.4427 0.144 Uiso 1 1 calc R . . H20B H 1.2631 0.0943 0.3355 0.144 Uiso 1 1 calc R . . H20C H 1.2109 0.0251 0.4241 0.144 Uiso 1 1 calc R . . C21 C 0.8014(3) 0.3311(2) 0.51497(14) 0.0485(5) Uani 1 1 d . . . C22 C 0.6355(5) 0.2625(4) 0.6237(2) 0.1061(12) Uani 1 1 d . . . H22A H 0.7340 0.2846 0.6808 0.159 Uiso 1 1 calc R . . H22B H 0.5580 0.1820 0.6332 0.159 Uiso 1 1 calc R . . H22C H 0.5747 0.3428 0.6143 0.159 Uiso 1 1 calc R . . C23 C -0.0509(4) -0.4047(3) -0.19477(17) 0.0696(8) Uani 1 1 d . . . H23A H -0.1059 -0.3279 -0.2227 0.104 Uiso 1 1 calc R . . H23B H -0.1295 -0.4926 -0.2171 0.104 Uiso 1 1 calc R . . H23C H 0.0537 -0.4091 -0.2155 0.104 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 0.0386(8) 0.0277(8) 0.0366(8) 0.0045(6) 0.0075(6) 0.0042(6) N2 0.0476(9) 0.0292(9) 0.0446(9) 0.0060(7) 0.0033(7) 0.0047(7) O1 0.0816(13) 0.1338(19) 0.0484(10) 0.0204(10) 0.0054(9) 0.0420(12) O2 0.0615(10) 0.0786(12) 0.0583(9) 0.0156(8) 0.0237(8) 0.0235(9) O3 0.143(2) 0.0727(13) 0.1070(15) -0.0470(12) 0.0821(15) -0.0515(13) O4 0.0899(12) 0.0615(10) 0.0631(10) -0.0102(8) 0.0432(9) -0.0211(9) O5 0.0608(9) 0.0391(8) 0.0549(9) -0.0047(6) 0.0083(7) -0.0079(7) C1 0.0467(11) 0.0337(10) 0.0410(10) 0.0057(8) 0.0021(8) 0.0025(8) C2 0.0409(10) 0.0317(10) 0.0356(9) 0.0030(7) 0.0100(8) 0.0019(8) C3 0.0366(9) 0.0305(10) 0.0354(9) -0.0003(7) 0.0126(7) 0.0015(7) C4 0.0383(9) 0.0304(10) 0.0432(10) 0.0022(8) 0.0156(8) 0.0061(8) C5 0.0529(12) 0.0345(11) 0.0528(12) -0.0018(9) 0.0115(9) 0.0070(9) C6 0.0604(13) 0.0313(11) 0.0692(14) -0.0023(10) 0.0200(11) 0.0041(9) C7 0.0643(13) 0.0329(11) 0.0718(14) 0.0124(10) 0.0274(12) 0.0131(10) C8 0.0546(12) 0.0392(12) 0.0563(12) 0.0123(9) 0.0152(10) 0.0124(9) C9 0.0400(10) 0.0343(10) 0.0479(10) 0.0068(8) 0.0164(8) 0.0091(8) C10 0.0411(10) 0.0387(11) 0.0408(10) 0.0042(8) 0.0061(8) 0.0078(8) C11 0.0344(9) 0.0340(10) 0.0376(9) 0.0035(7) 0.0086(8) 0.0057(7) C12 0.0346(9) 0.0334(10) 0.0400(10) 0.0017(8) 0.0065(8) 0.0054(8) C13 0.0480(11) 0.0405(11) 0.0429(10) 0.0040(8) 0.0160(9) -0.0008(9) C14 0.0497(11) 0.0482(12) 0.0387(10) -0.0036(9) 0.0156(9) -0.0006(9) C15 0.0367(10) 0.0344(10) 0.0476(11) -0.0003(8) 0.0060(8) 0.0036(8) C16 0.0468(11) 0.0419(11) 0.0463(11) 0.0119(9) 0.0058(9) -0.0028(9) C17 0.0450(11) 0.0477(12) 0.0357(10) 0.0073(8) 0.0054(8) 0.0011(9) C18 0.0436(10) 0.0335(10) 0.0361(10) 0.0034(8) 0.0090(8) -0.0030(8) C19 0.0438(11) 0.0468(12) 0.0407(11) 0.0050(9) 0.0039(9) -0.0022(9) C20 0.0766(19) 0.122(3) 0.106(2) 0.0173(19) 0.0359(17) 0.0479(19) C21 0.0541(12) 0.0426(12) 0.0434(11) -0.0054(9) 0.0138(9) -0.0087(9) C22 0.140(3) 0.103(2) 0.0798(19) -0.0185(17) 0.073(2) -0.036(2) C23 0.0816(17) 0.0594(15) 0.0600(15) -0.0172(12) 0.0253(12) -0.0177(13) _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 N2 1.365(3) . ? N1 C3 1.385(3) . ? N1 C11 1.394(3) . ? N2 C1 1.322(3) . ? O1 C19 1.183(3) . ? O2 C19 1.320(3) . ? O2 C20 1.444(3) . ? O3 C21 1.175(3) . ? O4 C21 1.308(3) . ? O4 C22 1.450(3) . ? O5 C15 1.366(3) . ? O5 C23 1.412(3) . ? C1 C2 1.394(3) . ? C1 H1 0.9300 . ? C2 C3 1.384(3) . ? C2 C18 1.506(3) . ? C3 C4 1.449(3) . ? C4 C5 1.402(3) . ? C4 C9 1.409(3) . ? C5 C6 1.380(3) . ? C5 H5 0.9300 . ? C6 C7 1.385(3) . ? C6 H6 0.9300 . ? C7 C8 1.372(3) . ? C7 H7 0.9300 . ? C8 C9 1.408(3) . ? C8 H8 0.9300 . ? C9 C10 1.430(3) . ? C10 C11 1.345(3) . ? C10 H10 0.9300 . ? C11 C12 1.477(3) . ? C12 C17 1.391(3) . ? C12 C13 1.393(3) . ? C13 C14 1.376(3) . ? C13 H13 0.9300 . ? C14 C15 1.380(3) . ? C14 H14 0.9300 . ? C15 C16 1.386(3) . ? C16 C17 1.373(3) . ? C16 H16 0.9300 . ? C17 H17 0.9300 . ? C18 C19 1.519(3) . ? C18 C21 1.521(3) . ? C18 H18 0.9800 . ? C20 H20A 0.9600 . ? C20 H20B 0.9600 . ? C20 H20C 0.9600 . ? C22 H22A 0.9600 . ? C22 H22B 0.9600 . ? C22 H22C 0.9600 . ? C23 H23A 0.9600 . ? C23 H23B 0.9600 . ? C23 H23C 0.9600 . ? 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 N2 N1 C3 112.11(16) . . ? N2 N1 C11 122.86(15) . . ? C3 N1 C11 124.80(16) . . ? C1 N2 N1 103.70(16) . . ? C19 O2 C20 118.1(2) . . ? C21 O4 C22 115.79(19) . . ? C15 O5 C23 118.04(17) . . ? N2 C1 C2 113.75(17) . . ? N2 C1 H1 123.1 . . ? C2 C1 H1 123.1 . . ? C3 C2 C1 104.74(16) . . ? C3 C2 C18 129.07(18) . . ? C1 C2 C18 126.18(17) . . ? C2 C3 N1 105.69(17) . . ? C2 C3 C4 136.01(16) . . ? N1 C3 C4 118.22(18) . . ? C5 C4 C9 118.89(19) . . ? C5 C4 C3 123.64(19) . . ? C9 C4 C3 117.46(16) . . ? C6 C5 C4 120.6(2) . . ? C6 C5 H5 119.7 . . ? C4 C5 H5 119.7 . . ? C5 C6 C7 120.5(2) . . ? C5 C6 H6 119.7 . . ? C7 C6 H6 119.7 . . ? C8 C7 C6 120.0(2) . . ? C8 C7 H7 120.0 . . ? C6 C7 H7 120.0 . . ? C7 C8 C9 120.8(2) . . ? C7 C8 H8 119.6 . . ? C9 C8 H8 119.6 . . ? C8 C9 C4 119.13(18) . . ? C8 C9 C10 121.3(2) . . ? C4 C9 C10 119.56(18) . . ? C11 C10 C9 123.49(19) . . ? C11 C10 H10 118.3 . . ? C9 C10 H10 118.3 . . ? C10 C11 N1 116.40(17) . . ? C10 C11 C12 124.32(19) . . ? N1 C11 C12 119.29(16) . . ? C17 C12 C13 117.41(18) . . ? C17 C12 C11 123.23(19) . . ? C13 C12 C11 119.29(17) . . ? C14 C13 C12 121.88(18) . . ? C14 C13 H13 119.1 . . ? C12 C13 H13 119.1 . . ? C13 C14 C15 119.67(19) . . ? C13 C14 H14 120.2 . . ? C15 C14 H14 120.2 . . ? O5 C15 C14 125.18(19) . . ? O5 C15 C16 115.39(18) . . ? C14 C15 C16 119.43(19) . . ? C17 C16 C15 120.48(19) . . ? C17 C16 H16 119.8 . . ? C15 C16 H16 119.8 . . ? C16 C17 C12 121.1(2) . . ? C16 C17 H17 119.5 . . ? C12 C17 H17 119.5 . . ? C2 C18 C19 112.23(17) . . ? C2 C18 C21 113.97(18) . . ? C19 C18 C21 109.62(17) . . ? C2 C18 H18 106.9 . . ? C19 C18 H18 106.9 . . ? C21 C18 H18 106.9 . . ? O1 C19 O2 123.7(2) . . ? O1 C19 C18 125.44(19) . . ? O2 C19 C18 110.81(17) . . ? O2 C20 H20A 109.5 . . ? O2 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? O2 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? O3 C21 O4 122.9(2) . . ? O3 C21 C18 124.0(2) . . ? O4 C21 C18 113.13(17) . . ? O4 C22 H22A 109.5 . . ? O4 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? O4 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? O5 C23 H23A 109.5 . . ? O5 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? O5 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? 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 C3 N1 N2 C1 0.6(2) . . . . ? C11 N1 N2 C1 175.41(15) . . . . ? N1 N2 C1 C2 -0.6(2) . . . . ? N2 C1 C2 C3 0.3(2) . . . . ? N2 C1 C2 C18 -178.82(16) . . . . ? C1 C2 C3 N1 0.07(19) . . . . ? C18 C2 C3 N1 179.19(16) . . . . ? C1 C2 C3 C4 -176.55(19) . . . . ? C18 C2 C3 C4 2.6(3) . . . . ? N2 N1 C3 C2 -0.44(19) . . . . ? C11 N1 C3 C2 -175.10(15) . . . . ? N2 N1 C3 C4 176.90(14) . . . . ? C11 N1 C3 C4 2.2(2) . . . . ? C2 C3 C4 C5 -5.6(3) . . . . ? N1 C3 C4 C5 178.05(16) . . . . ? C2 C3 C4 C9 173.44(19) . . . . ? N1 C3 C4 C9 -2.9(2) . . . . ? C9 C4 C5 C6 -1.6(3) . . . . ? C3 C4 C5 C6 177.47(18) . . . . ? C4 C5 C6 C7 2.2(3) . . . . ? C5 C6 C7 C8 -1.0(3) . . . . ? C6 C7 C8 C9 -0.7(3) . . . . ? C7 C8 C9 C4 1.3(3) . . . . ? C7 C8 C9 C10 -179.59(18) . . . . ? C5 C4 C9 C8 -0.1(3) . . . . ? C3 C4 C9 C8 -179.23(15) . . . . ? C5 C4 C9 C10 -179.26(16) . . . . ? C3 C4 C9 C10 1.6(3) . . . . ? C8 C9 C10 C11 -178.62(18) . . . . ? C4 C9 C10 C11 0.5(3) . . . . ? C9 C10 C11 N1 -1.3(3) . . . . ? C9 C10 C11 C12 179.19(16) . . . . ? N2 N1 C11 C10 -174.24(16) . . . . ? C3 N1 C11 C10 -0.1(3) . . . . ? N2 N1 C11 C12 5.3(2) . . . . ? C3 N1 C11 C12 179.41(15) . . . . ? C10 C11 C12 C17 -133.7(2) . . . . ? N1 C11 C12 C17 46.8(2) . . . . ? C10 C11 C12 C13 43.2(3) . . . . ? N1 C11 C12 C13 -136.31(19) . . . . ? C17 C12 C13 C14 -1.0(3) . . . . ? C11 C12 C13 C14 -178.02(17) . . . . ? C12 C13 C14 C15 -0.7(3) . . . . ? C23 O5 C15 C14 -6.4(3) . . . . ? C23 O5 C15 C16 172.9(2) . . . . ? C13 C14 C15 O5 -178.75(17) . . . . ? C13 C14 C15 C16 2.0(3) . . . . ? O5 C15 C16 C17 179.02(17) . . . . ? C14 C15 C16 C17 -1.7(3) . . . . ? C15 C16 C17 C12 0.0(3) . . . . ? C13 C12 C17 C16 1.3(3) . . . . ? C11 C12 C17 C16 178.26(17) . . . . ? C3 C2 C18 C19 -145.30(19) . . . . ? C1 C2 C18 C19 33.6(3) . . . . ? C3 C2 C18 C21 89.3(2) . . . . ? C1 C2 C18 C21 -91.7(2) . . . . ? C20 O2 C19 O1 -0.1(4) . . . . ? C20 O2 C19 C18 178.4(2) . . . . ? C2 C18 C19 O1 -124.7(2) . . . . ? C21 C18 C19 O1 3.0(3) . . . . ? C2 C18 C19 O2 56.8(2) . . . . ? C21 C18 C19 O2 -175.48(16) . . . . ? C22 O4 C21 O3 0.0(4) . . . . ? C22 O4 C21 C18 178.9(3) . . . . ? C2 C18 C21 O3 -139.1(3) . . . . ? C19 C18 C21 O3 94.2(3) . . . . ? C2 C18 C21 O4 42.1(3) . . . . ? C19 C18 C21 O4 -84.7(2) . . . . ? _diffrn_measured_fraction_theta_max 0.975 _diffrn_reflns_theta_full 25.01 _diffrn_measured_fraction_theta_full 0.975 _refine_diff_density_max 0.343 _refine_diff_density_min -0.385 _refine_diff_density_rms 0.105