# Electronic Supplementary Material (ESI) for Chemical Science # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full 'Chemical Science' _journal_coden_cambridge 1475 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_email thegrimreaperlfc@gmail.com _publ_contact_author_name 'Wei Meng' loop_ _publ_author_name 'Wei Meng' 'Jun-an Ma' data_110622c _database_code_depnum_ccdc_archive 'CCDC 839553' #TrackingRef '110622C.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C28 H26 O4' _chemical_formula_weight 426.49 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' 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 P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 13.830(3) _cell_length_b 8.0116(14) _cell_length_c 21.166(4) _cell_angle_alpha 90.00 _cell_angle_beta 104.203(8) _cell_angle_gamma 90.00 _cell_volume 2273.5(8) _cell_formula_units_Z 4 _cell_measurement_temperature 294(2) _cell_measurement_reflns_used 4961 _cell_measurement_theta_min 3.0 _cell_measurement_theta_max 27.5 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.246 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 904 _exptl_absorpt_coefficient_mu 0.082 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9717 _exptl_absorpt_correction_T_max 0.9894 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 294(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 RigakuMERCURY375R _diffrn_measurement_method 'profile data from \w-scans' _diffrn_detector_area_resol_mean 13.6612 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 22903 _diffrn_reflns_av_R_equivalents 0.0513 _diffrn_reflns_av_sigmaI/netI 0.0312 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 3.00 _diffrn_reflns_theta_max 27.46 _reflns_number_total 5175 _reflns_number_gt 3969 _reflns_threshold_expression >2sigma(I) _computing_data_collection CRYSTALCLEAR _computing_cell_refinement CRYSTALCLEAR _computing_data_reduction CRYSTALCLEAR _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^)+(0.1039P)^2^+0.3483P] 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 5175 _refine_ls_number_parameters 292 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0768 _refine_ls_R_factor_gt 0.0616 _refine_ls_wR_factor_ref 0.1851 _refine_ls_wR_factor_gt 0.1690 _refine_ls_goodness_of_fit_ref 1.051 _refine_ls_restrained_S_all 1.051 _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 C1 C 0.12322(12) 0.6109(2) 0.90833(8) 0.0444(4) Uani 1 1 d . . . C2 C 0.05335(13) 0.6726(2) 0.94258(9) 0.0516(4) Uani 1 1 d . . . H2 H 0.0727 0.6822 0.9877 0.062 Uiso 1 1 calc R . . C3 C -0.04081(14) 0.7177(3) 0.91055(11) 0.0608(5) Uani 1 1 d . . . H3 H -0.0843 0.7584 0.9341 0.073 Uiso 1 1 calc R . . C4 C -0.07324(15) 0.7037(3) 0.84285(11) 0.0644(5) Uani 1 1 d . . . H4 H -0.1376 0.7360 0.8217 0.077 Uiso 1 1 calc R . . C5 C -0.01095(15) 0.6434(3) 0.80826(10) 0.0624(5) Uani 1 1 d . . . H5 H -0.0338 0.6328 0.7633 0.075 Uiso 1 1 calc R . . C6 C 0.08906(14) 0.5953(2) 0.83881(9) 0.0509(4) Uani 1 1 d . . . C7 C 0.15407(16) 0.5310(3) 0.80413(9) 0.0598(5) Uani 1 1 d . . . H7 H 0.1321 0.5213 0.7591 0.072 Uiso 1 1 calc R . . C8 C 0.25032(15) 0.4811(2) 0.83421(9) 0.0545(4) Uani 1 1 d . . . C9 C 0.31611(19) 0.4153(3) 0.79771(11) 0.0731(6) Uani 1 1 d . . . H9 H 0.2933 0.4023 0.7529 0.088 Uiso 1 1 calc R . . C10 C 0.4111(2) 0.3718(3) 0.82736(13) 0.0771(7) Uani 1 1 d . . . H10 H 0.4529 0.3308 0.8027 0.093 Uiso 1 1 calc R . . C11 C 0.44664(16) 0.3883(3) 0.89496(11) 0.0636(5) Uani 1 1 d . . . H11 H 0.5120 0.3583 0.9148 0.076 Uiso 1 1 calc R . . C12 C 0.38610(13) 0.4479(2) 0.93179(10) 0.0520(4) Uani 1 1 d . . . H12 H 0.4110 0.4577 0.9766 0.062 Uiso 1 1 calc R . . C13 C 0.28548(13) 0.4957(2) 0.90332(8) 0.0460(4) Uani 1 1 d . . . C14 C 0.22142(12) 0.56168(19) 0.93994(8) 0.0420(4) Uani 1 1 d . . . C15 C 0.25594(11) 0.57965(18) 1.01231(8) 0.0398(3) Uani 1 1 d . . . C16 C 0.26499(11) 0.75008(19) 1.03991(7) 0.0399(3) Uani 1 1 d . . . C17 C 0.29837(13) 0.8861(2) 1.00169(8) 0.0469(4) Uani 1 1 d . . . C18 C 0.3914(2) 0.9522(3) 0.92528(12) 0.0756(6) Uani 1 1 d . . . H18A H 0.4238 1.0483 0.9494 0.091 Uiso 1 1 calc R . . H18B H 0.3320 0.9903 0.8939 0.091 Uiso 1 1 calc R . . C19 C 0.4591(2) 0.8710(4) 0.89144(15) 0.0982(9) Uani 1 1 d . . . H19A H 0.5144 0.8235 0.9229 0.147 Uiso 1 1 calc R . . H19B H 0.4833 0.9519 0.8656 0.147 Uiso 1 1 calc R . . H19C H 0.4241 0.7843 0.8637 0.147 Uiso 1 1 calc R . . C20 C 0.24469(11) 0.78875(19) 1.09775(8) 0.0412(3) Uani 1 1 d . . . C21 C 0.26658(16) 0.9531(2) 1.13248(10) 0.0584(5) Uani 1 1 d . . . H21A H 0.3167 1.0114 1.1168 0.088 Uiso 1 1 calc R . . H21B H 0.2902 0.9339 1.1785 0.088 Uiso 1 1 calc R . . H21C H 0.2068 1.0190 1.1244 0.088 Uiso 1 1 calc R . . C22 C 0.19966(12) 0.6523(2) 1.13093(8) 0.0422(4) Uani 1 1 d . . . H22 H 0.1510 0.5925 1.0970 0.051 Uiso 1 1 calc R . . C23 C 0.14513(13) 0.7167(2) 1.17967(8) 0.0459(4) Uani 1 1 d . . . C24 C -0.00435(15) 0.8512(3) 1.18791(10) 0.0617(5) Uani 1 1 d . . . H24A H 0.0272 0.9474 1.2123 0.074 Uiso 1 1 calc R . . H24B H -0.0157 0.7678 1.2185 0.074 Uiso 1 1 calc R . . C25 C -0.10049(16) 0.9002(3) 1.14262(14) 0.0796(7) Uani 1 1 d . . . H25A H -0.0883 0.9833 1.1128 0.119 Uiso 1 1 calc R . . H25B H -0.1444 0.9448 1.1672 0.119 Uiso 1 1 calc R . . H25C H -0.1307 0.8040 1.1186 0.119 Uiso 1 1 calc R . . C26 C 0.28249(13) 0.5334(2) 1.15893(9) 0.0497(4) Uani 1 1 d . . . H26 H 0.3099 0.5296 1.2037 0.060 Uiso 1 1 calc R . . C27 C 0.31631(13) 0.4336(2) 1.11935(9) 0.0511(4) Uani 1 1 d . . . H27 H 0.3648 0.3553 1.1375 0.061 Uiso 1 1 calc R . . C28 C 0.28139(12) 0.4405(2) 1.04923(9) 0.0461(4) Uani 1 1 d . . . H28 H 0.2758 0.3393 1.0271 0.055 Uiso 1 1 calc R . . O1 O 0.26944(14) 1.02771(17) 0.99884(8) 0.0760(5) Uani 1 1 d . . . O2 O 0.36438(10) 0.83252(16) 0.96978(7) 0.0574(3) Uani 1 1 d . . . O3 O 0.17413(11) 0.7092(2) 1.23779(6) 0.0647(4) Uani 1 1 d . . . O4 O 0.05847(10) 0.78385(18) 1.14850(6) 0.0567(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 0.0444(8) 0.0383(8) 0.0494(9) 0.0019(6) 0.0098(7) -0.0061(6) C2 0.0459(9) 0.0516(10) 0.0570(10) 0.0003(8) 0.0118(8) -0.0018(7) C3 0.0454(9) 0.0622(12) 0.0748(13) 0.0069(9) 0.0148(9) 0.0001(8) C4 0.0462(9) 0.0629(12) 0.0775(13) 0.0140(10) 0.0028(9) -0.0058(8) C5 0.0609(11) 0.0645(12) 0.0540(10) 0.0102(9) -0.0009(9) -0.0149(9) C6 0.0548(10) 0.0475(9) 0.0486(9) 0.0029(7) 0.0090(8) -0.0107(7) C7 0.0710(12) 0.0644(12) 0.0426(9) -0.0007(8) 0.0112(9) -0.0110(10) C8 0.0645(11) 0.0536(10) 0.0493(10) -0.0060(7) 0.0217(9) -0.0099(8) C9 0.0890(16) 0.0821(15) 0.0575(12) -0.0156(10) 0.0359(12) -0.0091(12) C10 0.0841(16) 0.0768(15) 0.0866(16) -0.0183(12) 0.0516(14) -0.0023(12) C11 0.0628(11) 0.0549(11) 0.0816(14) -0.0084(10) 0.0340(11) -0.0008(9) C12 0.0499(9) 0.0479(9) 0.0621(11) -0.0059(8) 0.0216(8) -0.0021(7) C13 0.0506(9) 0.0403(8) 0.0503(9) -0.0055(7) 0.0188(7) -0.0079(7) C14 0.0443(8) 0.0355(7) 0.0475(9) -0.0017(6) 0.0138(7) -0.0051(6) C15 0.0386(7) 0.0364(7) 0.0461(8) -0.0011(6) 0.0139(6) -0.0009(6) C16 0.0394(7) 0.0358(8) 0.0435(8) 0.0010(6) 0.0084(6) 0.0009(6) C17 0.0545(9) 0.0384(8) 0.0468(9) 0.0013(6) 0.0107(7) -0.0028(7) C18 0.0851(15) 0.0668(13) 0.0841(15) 0.0198(11) 0.0384(13) -0.0082(11) C19 0.112(2) 0.098(2) 0.105(2) 0.0214(16) 0.0676(18) -0.0008(17) C20 0.0409(8) 0.0382(8) 0.0428(8) -0.0011(6) 0.0067(6) 0.0021(6) C21 0.0703(12) 0.0472(10) 0.0597(11) -0.0129(8) 0.0198(9) -0.0071(8) C22 0.0438(8) 0.0416(8) 0.0415(8) 0.0002(6) 0.0108(7) 0.0013(6) C23 0.0485(9) 0.0451(8) 0.0445(9) -0.0014(7) 0.0120(7) -0.0008(7) C24 0.0575(10) 0.0652(12) 0.0688(12) -0.0101(9) 0.0281(10) 0.0029(9) C25 0.0555(12) 0.0826(16) 0.1045(19) -0.0003(13) 0.0267(12) 0.0112(11) C26 0.0525(9) 0.0492(9) 0.0466(9) 0.0098(7) 0.0109(7) 0.0067(7) C27 0.0521(9) 0.0436(9) 0.0594(10) 0.0132(7) 0.0174(8) 0.0112(7) C28 0.0502(9) 0.0365(8) 0.0553(9) 0.0001(6) 0.0200(8) 0.0026(6) O1 0.1080(12) 0.0404(7) 0.0892(11) 0.0142(7) 0.0423(10) 0.0112(7) O2 0.0631(8) 0.0482(7) 0.0684(8) 0.0062(6) 0.0304(7) -0.0061(6) O3 0.0709(9) 0.0799(10) 0.0416(7) -0.0059(6) 0.0107(6) 0.0104(7) O4 0.0520(7) 0.0699(8) 0.0509(7) 0.0006(6) 0.0178(6) 0.0125(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C14 1.415(2) . ? C1 C2 1.431(3) . ? C1 C6 1.436(2) . ? C2 C3 1.361(3) . ? C2 H2 0.9300 . ? C3 C4 1.397(3) . ? C3 H3 0.9300 . ? C4 C5 1.350(3) . ? C4 H4 0.9300 . ? C5 C6 1.428(3) . ? C5 H5 0.9300 . ? C6 C7 1.391(3) . ? C7 C8 1.386(3) . ? C7 H7 0.9300 . ? C8 C13 1.428(2) . ? C8 C9 1.431(3) . ? C9 C10 1.355(4) . ? C9 H9 0.9300 . ? C10 C11 1.401(3) . ? C10 H10 0.9300 . ? C11 C12 1.363(3) . ? C11 H11 0.9300 . ? C12 C13 1.426(3) . ? C12 H12 0.9300 . ? C13 C14 1.415(2) . ? C14 C15 1.495(2) . ? C15 C28 1.357(2) . ? C15 C16 1.478(2) . ? C16 C20 1.357(2) . ? C16 C17 1.496(2) . ? C17 O1 1.199(2) . ? C17 O2 1.333(2) . ? C18 O2 1.456(2) . ? C18 C19 1.464(4) . ? C18 H18A 0.9700 . ? C18 H18B 0.9700 . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 0.9600 . ? C20 C21 1.502(2) . ? C20 C22 1.513(2) . ? C21 H21A 0.9600 . ? C21 H21B 0.9600 . ? C21 H21C 0.9600 . ? C22 C26 1.496(2) . ? C22 C23 1.510(2) . ? C22 H22 0.9800 . ? C23 O3 1.198(2) . ? C23 O4 1.331(2) . ? C24 O4 1.448(2) . ? C24 C25 1.488(3) . ? C24 H24A 0.9700 . ? C24 H24B 0.9700 . ? C25 H25A 0.9600 . ? C25 H25B 0.9600 . ? C25 H25C 0.9600 . ? C26 C27 1.324(3) . ? C26 H26 0.9300 . ? C27 C28 1.445(3) . ? C27 H27 0.9300 . ? C28 H28 0.9300 . ? 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 C1 C2 123.09(15) . . ? C14 C1 C6 119.77(16) . . ? C2 C1 C6 117.12(16) . . ? C3 C2 C1 121.45(18) . . ? C3 C2 H2 119.3 . . ? C1 C2 H2 119.3 . . ? C2 C3 C4 121.1(2) . . ? C2 C3 H3 119.4 . . ? C4 C3 H3 119.4 . . ? C5 C4 C3 119.87(18) . . ? C5 C4 H4 120.1 . . ? C3 C4 H4 120.1 . . ? C4 C5 C6 121.80(18) . . ? C4 C5 H5 119.1 . . ? C6 C5 H5 119.1 . . ? C7 C6 C5 122.69(17) . . ? C7 C6 C1 118.68(17) . . ? C5 C6 C1 118.61(18) . . ? C8 C7 C6 122.45(17) . . ? C8 C7 H7 118.8 . . ? C6 C7 H7 118.8 . . ? C7 C8 C13 119.59(17) . . ? C7 C8 C9 121.63(18) . . ? C13 C8 C9 118.78(19) . . ? C10 C9 C8 121.1(2) . . ? C10 C9 H9 119.4 . . ? C8 C9 H9 119.4 . . ? C9 C10 C11 120.44(19) . . ? C9 C10 H10 119.8 . . ? C11 C10 H10 119.8 . . ? C12 C11 C10 120.4(2) . . ? C12 C11 H11 119.8 . . ? C10 C11 H11 119.8 . . ? C11 C12 C13 121.67(18) . . ? C11 C12 H12 119.2 . . ? C13 C12 H12 119.2 . . ? C14 C13 C12 123.08(16) . . ? C14 C13 C8 119.34(16) . . ? C12 C13 C8 117.54(16) . . ? C1 C14 C13 120.16(15) . . ? C1 C14 C15 119.06(14) . . ? C13 C14 C15 120.78(14) . . ? C28 C15 C16 123.11(15) . . ? C28 C15 C14 118.90(14) . . ? C16 C15 C14 117.94(13) . . ? C20 C16 C15 123.44(14) . . ? C20 C16 C17 118.74(14) . . ? C15 C16 C17 117.81(14) . . ? O1 C17 O2 122.74(16) . . ? O1 C17 C16 124.94(17) . . ? O2 C17 C16 112.31(14) . . ? O2 C18 C19 108.7(2) . . ? O2 C18 H18A 110.0 . . ? C19 C18 H18A 110.0 . . ? O2 C18 H18B 110.0 . . ? C19 C18 H18B 110.0 . . ? H18A C18 H18B 108.3 . . ? C18 C19 H19A 109.5 . . ? C18 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C18 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C16 C20 C21 125.45(15) . . ? C16 C20 C22 116.96(14) . . ? C21 C20 C22 117.55(14) . . ? C20 C21 H21A 109.5 . . ? C20 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C20 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C26 C22 C23 114.15(13) . . ? C26 C22 C20 106.36(13) . . ? C23 C22 C20 113.66(13) . . ? C26 C22 H22 107.4 . . ? C23 C22 H22 107.4 . . ? C20 C22 H22 107.4 . . ? O3 C23 O4 124.27(16) . . ? O3 C23 C22 125.91(16) . . ? O4 C23 C22 109.82(13) . . ? O4 C24 C25 107.13(17) . . ? O4 C24 H24A 110.3 . . ? C25 C24 H24A 110.3 . . ? O4 C24 H24B 110.3 . . ? C25 C24 H24B 110.3 . . ? H24A C24 H24B 108.5 . . ? C24 C25 H25A 109.5 . . ? C24 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? C24 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? C27 C26 C22 119.28(16) . . ? C27 C26 H26 120.4 . . ? C22 C26 H26 120.4 . . ? C26 C27 C28 123.09(15) . . ? C26 C27 H27 118.5 . . ? C28 C27 H27 118.5 . . ? C15 C28 C27 126.68(15) . . ? C15 C28 H28 116.7 . . ? C27 C28 H28 116.7 . . ? C17 O2 C18 115.59(16) . . ? C23 O4 C24 117.33(14) . . ? 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 C14 C1 C2 C3 -179.51(17) . . . . ? C6 C1 C2 C3 -1.2(3) . . . . ? C1 C2 C3 C4 0.6(3) . . . . ? C2 C3 C4 C5 0.6(3) . . . . ? C3 C4 C5 C6 -1.1(3) . . . . ? C4 C5 C6 C7 179.25(19) . . . . ? C4 C5 C6 C1 0.5(3) . . . . ? C14 C1 C6 C7 0.2(2) . . . . ? C2 C1 C6 C7 -178.13(16) . . . . ? C14 C1 C6 C5 179.01(16) . . . . ? C2 C1 C6 C5 0.7(2) . . . . ? C5 C6 C7 C8 -178.51(18) . . . . ? C1 C6 C7 C8 0.2(3) . . . . ? C6 C7 C8 C13 -0.2(3) . . . . ? C6 C7 C8 C9 -179.97(19) . . . . ? C7 C8 C9 C10 177.9(2) . . . . ? C13 C8 C9 C10 -1.9(3) . . . . ? C8 C9 C10 C11 0.9(4) . . . . ? C9 C10 C11 C12 0.2(3) . . . . ? C10 C11 C12 C13 -0.2(3) . . . . ? C11 C12 C13 C14 -178.46(17) . . . . ? C11 C12 C13 C8 -0.8(3) . . . . ? C7 C8 C13 C14 -0.2(3) . . . . ? C9 C8 C13 C14 179.51(17) . . . . ? C7 C8 C13 C12 -177.95(17) . . . . ? C9 C8 C13 C12 1.8(3) . . . . ? C2 C1 C14 C13 177.57(15) . . . . ? C6 C1 C14 C13 -0.7(2) . . . . ? C2 C1 C14 C15 -2.1(2) . . . . ? C6 C1 C14 C15 179.67(14) . . . . ? C12 C13 C14 C1 178.25(15) . . . . ? C8 C13 C14 C1 0.7(2) . . . . ? C12 C13 C14 C15 -2.1(2) . . . . ? C8 C13 C14 C15 -179.66(14) . . . . ? C1 C14 C15 C28 117.19(17) . . . . ? C13 C14 C15 C28 -62.5(2) . . . . ? C1 C14 C15 C16 -65.55(19) . . . . ? C13 C14 C15 C16 114.79(17) . . . . ? C28 C15 C16 C20 -38.0(2) . . . . ? C14 C15 C16 C20 144.89(15) . . . . ? C28 C15 C16 C17 142.01(16) . . . . ? C14 C15 C16 C17 -35.1(2) . . . . ? C20 C16 C17 O1 -35.3(3) . . . . ? C15 C16 C17 O1 144.68(19) . . . . ? C20 C16 C17 O2 145.31(15) . . . . ? C15 C16 C17 O2 -34.7(2) . . . . ? C15 C16 C20 C21 170.63(16) . . . . ? C17 C16 C20 C21 -9.3(2) . . . . ? C15 C16 C20 C22 -7.0(2) . . . . ? C17 C16 C20 C22 173.00(14) . . . . ? C16 C20 C22 C26 74.85(18) . . . . ? C21 C20 C22 C26 -103.00(17) . . . . ? C16 C20 C22 C23 -158.69(14) . . . . ? C21 C20 C22 C23 23.5(2) . . . . ? C26 C22 C23 O3 16.2(3) . . . . ? C20 C22 C23 O3 -106.1(2) . . . . ? C26 C22 C23 O4 -163.57(15) . . . . ? C20 C22 C23 O4 74.18(18) . . . . ? C23 C22 C26 C27 160.84(17) . . . . ? C20 C22 C26 C27 -73.0(2) . . . . ? C22 C26 C27 C28 4.0(3) . . . . ? C16 C15 C28 C27 2.8(3) . . . . ? C14 C15 C28 C27 179.88(15) . . . . ? C26 C27 C28 C15 36.6(3) . . . . ? O1 C17 O2 C18 -6.5(3) . . . . ? C16 C17 O2 C18 172.86(17) . . . . ? C19 C18 O2 C17 -176.5(2) . . . . ? O3 C23 O4 C24 -0.2(3) . . . . ? C22 C23 O4 C24 179.53(15) . . . . ? C25 C24 O4 C23 -173.61(18) . . . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 27.46 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.275 _refine_diff_density_min -0.210 _refine_diff_density_rms 0.044 data_r90402a _database_code_depnum_ccdc_archive 'CCDC 839605' #TrackingRef 'r90402a.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H25 N3 O7' _chemical_formula_weight 443.45 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 Cc loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x, -y, z+1/2' 'x+1/2, y+1/2, z' 'x+1/2, -y+1/2, z+1/2' _cell_length_a 15.778(3) _cell_length_b 16.681(3) _cell_length_c 8.3240(17) _cell_angle_alpha 90.00 _cell_angle_beta 95.55(3) _cell_angle_gamma 90.00 _cell_volume 2180.5(8) _cell_formula_units_Z 4 _cell_measurement_temperature 113(2) _cell_measurement_reflns_used 3442 _cell_measurement_theta_min 1.781 _cell_measurement_theta_max 27.065 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.351 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 936 _exptl_absorpt_coefficient_mu 0.102 _exptl_absorpt_correction_type MULTI-SCAN _exptl_absorpt_correction_T_min 0.9799 _exptl_absorpt_correction_T_max 0.9879 _exptl_absorpt_process_details crystalclear _exptl_special_details ; ? ; _diffrn_ambient_temperature 113(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating anode' _diffrn_radiation_monochromator confocal _diffrn_measurement_device_type 'rigaku saturn' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 7249 _diffrn_reflns_av_R_equivalents 0.0529 _diffrn_reflns_av_sigmaI/netI 0.1101 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 1.78 _diffrn_reflns_theta_max 25.02 _reflns_number_total 3236 _reflns_number_gt 2049 _reflns_threshold_expression >2sigma(I) _computing_data_collection crystalclear _computing_cell_refinement crystalclear _computing_data_reduction crystalclear _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^)+(0.0585P)^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 0.0263(15) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -1.9(14) _refine_ls_number_reflns 3236 _refine_ls_number_parameters 293 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0638 _refine_ls_R_factor_gt 0.0469 _refine_ls_wR_factor_ref 0.1147 _refine_ls_wR_factor_gt 0.1033 _refine_ls_goodness_of_fit_ref 0.849 _refine_ls_restrained_S_all 0.849 _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 0.47726(17) 0.02043(16) 0.1963(3) 0.0305(7) Uani 1 1 d . . . O2 O 0.79718(18) 0.33022(16) 0.4009(3) 0.0359(8) Uani 1 1 d . . . O3 O 0.8330(2) 0.25469(19) 0.1956(4) 0.0498(9) Uani 1 1 d . . . O4 O 0.80771(16) 0.05393(16) 0.7412(3) 0.0269(7) Uani 1 1 d . . . O5 O 0.69216(17) 0.06813(16) 0.8799(3) 0.0282(7) Uani 1 1 d . . . O6 O 0.5940(2) 0.48350(19) 0.9963(4) 0.0479(9) Uani 1 1 d . . . O7 O 0.5336(2) 0.4080(2) 1.1633(4) 0.0649(11) Uani 1 1 d . . . N1 N 0.56557(19) 0.11076(18) 0.3368(3) 0.0201(7) Uani 1 1 d . . . N2 N 0.5611(2) 0.17466(18) 0.4537(4) 0.0213(7) Uani 1 1 d . . . N3 N 0.5671(2) 0.4185(3) 1.0370(4) 0.0411(10) Uani 1 1 d . . . C1 C 0.4887(2) 0.0726(2) 0.2994(4) 0.0232(9) Uani 1 1 d . . . C2 C 0.4258(2) 0.1092(2) 0.4019(4) 0.0267(9) Uani 1 1 d . . . H2A H 0.4192 0.0769 0.4968 0.032 Uiso 1 1 calc R . . H2B H 0.3707 0.1166 0.3414 0.032 Uiso 1 1 calc R . . C3 C 0.4683(2) 0.1898(2) 0.4471(4) 0.0231(9) Uani 1 1 d . . . H3A H 0.4512 0.2301 0.3666 0.028 Uiso 1 1 calc R . . H3B H 0.4529 0.2080 0.5511 0.028 Uiso 1 1 calc R . . C4 C 0.5973(2) 0.1476(2) 0.6172(4) 0.0193(8) Uani 1 1 d . . . H4 H 0.5631 0.1033 0.6535 0.023 Uiso 1 1 calc R . . C5 C 0.6900(2) 0.1184(2) 0.6048(4) 0.0206(8) Uani 1 1 d . . . H5 H 0.6866 0.0769 0.5209 0.025 Uiso 1 1 calc R . . C6 C 0.7465(2) 0.1841(2) 0.5483(4) 0.0218(9) Uani 1 1 d . . . C7 C 0.7474(2) 0.1962(2) 0.3862(4) 0.0230(9) Uani 1 1 d . . . C8 C 0.7083(2) 0.1431(2) 0.2592(4) 0.0232(9) Uani 1 1 d . . . H8 H 0.7421 0.1340 0.1754 0.028 Uiso 1 1 calc R . . C9 C 0.6330(3) 0.1055(2) 0.2414(4) 0.0238(9) Uani 1 1 d . . . H9 H 0.6247 0.0711 0.1533 0.029 Uiso 1 1 calc R . . C10 C 0.7979(2) 0.2613(2) 0.3179(5) 0.0274(10) Uani 1 1 d . . . C11 C 0.8375(3) 0.3994(2) 0.3338(5) 0.0355(11) Uani 1 1 d . . . H11A H 0.8846 0.3819 0.2757 0.043 Uiso 1 1 calc R . . H11B H 0.8599 0.4347 0.4205 0.043 Uiso 1 1 calc R . . C12 C 0.7741(3) 0.4440(3) 0.2217(5) 0.0444(12) Uani 1 1 d . . . H12A H 0.7575 0.4113 0.1290 0.067 Uiso 1 1 calc R . . H12B H 0.7993 0.4928 0.1878 0.067 Uiso 1 1 calc R . . H12C H 0.7249 0.4564 0.2764 0.067 Uiso 1 1 calc R . . C13 C 0.7976(3) 0.2323(2) 0.6757(5) 0.0329(11) Uani 1 1 d . . . H13A H 0.8570 0.2203 0.6735 0.049 Uiso 1 1 calc R . . H13B H 0.7803 0.2191 0.7799 0.049 Uiso 1 1 calc R . . H13C H 0.7883 0.2884 0.6552 0.049 Uiso 1 1 calc R . . C14 C 0.7276(2) 0.0784(2) 0.7586(4) 0.0215(9) Uani 1 1 d . . . C15 C 0.8567(2) 0.0175(2) 0.8816(5) 0.0287(10) Uani 1 1 d . . . H15A H 0.8948 -0.0229 0.8455 0.034 Uiso 1 1 calc R . . H15B H 0.8182 -0.0085 0.9492 0.034 Uiso 1 1 calc R . . C16 C 0.9075(3) 0.0803(3) 0.9775(5) 0.0336(11) Uani 1 1 d . . . H16A H 0.9433 0.1079 0.9088 0.050 Uiso 1 1 calc R . . H16B H 0.9422 0.0552 1.0645 0.050 Uiso 1 1 calc R . . H16C H 0.8695 0.1178 1.0206 0.050 Uiso 1 1 calc R . . C17 C 0.5908(2) 0.2198(2) 0.7288(4) 0.0221(9) Uani 1 1 d . . . C18 C 0.5673(2) 0.2081(2) 0.8845(4) 0.0268(9) Uani 1 1 d . . . H18 H 0.5566 0.1565 0.9198 0.032 Uiso 1 1 calc R . . C19 C 0.5596(3) 0.2730(2) 0.9875(5) 0.0319(10) Uani 1 1 d . . . H19 H 0.5447 0.2656 1.0919 0.038 Uiso 1 1 calc R . . C20 C 0.5747(3) 0.3487(3) 0.9297(5) 0.0295(10) Uani 1 1 d . . . C21 C 0.5965(3) 0.3637(3) 0.7757(5) 0.0310(10) Uani 1 1 d . . . H21 H 0.6054 0.4156 0.7402 0.037 Uiso 1 1 calc R . . C22 C 0.6045(3) 0.2975(2) 0.6756(4) 0.0284(10) Uani 1 1 d . . . H22 H 0.6194 0.3054 0.5714 0.034 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 0.0355(16) 0.0260(16) 0.0293(16) -0.0077(12) 0.0002(12) -0.0043(13) O2 0.058(2) 0.0226(17) 0.0298(17) 0.0011(12) 0.0159(14) -0.0075(14) O3 0.069(2) 0.041(2) 0.045(2) -0.0109(16) 0.0344(17) -0.0170(18) O4 0.0262(15) 0.0355(17) 0.0186(14) 0.0032(12) -0.0002(11) 0.0070(13) O5 0.0391(17) 0.0263(16) 0.0204(15) 0.0000(11) 0.0087(13) 0.0043(13) O6 0.070(2) 0.030(2) 0.041(2) -0.0115(15) -0.0025(16) 0.0094(18) O7 0.098(3) 0.061(3) 0.040(2) -0.0203(17) 0.030(2) 0.010(2) N1 0.0226(17) 0.0218(19) 0.0156(16) -0.0044(13) 0.0000(13) -0.0020(14) N2 0.0294(17) 0.0200(18) 0.0148(16) -0.0032(12) 0.0032(13) 0.0002(14) N3 0.046(2) 0.042(3) 0.034(2) -0.0127(18) 0.0004(19) 0.014(2) C1 0.025(2) 0.024(2) 0.020(2) 0.0040(17) -0.0017(16) -0.0009(19) C2 0.025(2) 0.031(2) 0.024(2) 0.0026(16) -0.0011(17) -0.0027(18) C3 0.024(2) 0.027(2) 0.017(2) -0.0036(16) 0.0010(17) 0.0025(17) C4 0.0240(19) 0.021(2) 0.0131(19) -0.0006(14) 0.0015(15) -0.0034(17) C5 0.029(2) 0.019(2) 0.0139(19) -0.0007(14) 0.0046(16) 0.0014(17) C6 0.024(2) 0.022(2) 0.019(2) -0.0021(16) 0.0005(16) -0.0021(17) C7 0.027(2) 0.021(2) 0.021(2) 0.0012(16) 0.0067(16) -0.0026(18) C8 0.032(2) 0.024(2) 0.015(2) -0.0007(15) 0.0062(17) 0.0009(18) C9 0.035(2) 0.021(2) 0.0153(19) -0.0019(16) 0.0047(17) 0.0032(18) C10 0.034(2) 0.021(2) 0.028(2) -0.0013(17) 0.0053(19) -0.0084(18) C11 0.048(3) 0.023(3) 0.036(2) 0.0059(19) 0.006(2) -0.013(2) C12 0.053(3) 0.033(3) 0.047(3) 0.003(2) 0.008(2) -0.004(2) C13 0.042(3) 0.031(3) 0.025(2) -0.0014(18) 0.0027(19) -0.011(2) C14 0.026(2) 0.021(2) 0.017(2) 0.0005(15) -0.0033(17) -0.0022(17) C15 0.026(2) 0.032(3) 0.027(2) 0.0074(18) -0.0040(17) 0.0085(18) C16 0.030(2) 0.043(3) 0.027(2) 0.0013(18) -0.0031(19) 0.002(2) C17 0.021(2) 0.026(2) 0.019(2) -0.0007(15) 0.0032(16) -0.0011(17) C18 0.033(2) 0.028(2) 0.020(2) 0.0053(16) 0.0083(18) 0.0061(19) C19 0.042(2) 0.034(3) 0.020(2) -0.0023(18) 0.0058(18) 0.008(2) C20 0.036(2) 0.030(2) 0.023(2) -0.0093(17) 0.0049(18) 0.0059(19) C21 0.040(2) 0.028(2) 0.025(2) -0.0031(17) 0.0009(19) -0.002(2) C22 0.042(2) 0.020(2) 0.024(2) -0.0004(16) 0.0086(19) -0.0018(19) _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 1.223(4) . ? O2 C10 1.342(4) . ? O2 C11 1.456(4) . ? O3 C10 1.210(4) . ? O4 C14 1.350(4) . ? O4 C15 1.469(4) . ? O5 C14 1.213(4) . ? O6 N3 1.225(5) . ? O7 N3 1.234(5) . ? N1 C1 1.379(5) . ? N1 C9 1.391(5) . ? N1 N2 1.450(4) . ? N2 C3 1.480(5) . ? N2 C4 1.494(4) . ? N3 C20 1.478(5) . ? C1 C2 1.500(5) . ? C2 C3 1.533(5) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 C17 1.531(5) . ? C4 C5 1.554(5) . ? C4 H4 0.9800 . ? C5 C14 1.512(5) . ? C5 C6 1.517(5) . ? C5 H5 0.9800 . ? C6 C7 1.366(5) . ? C6 C13 1.503(5) . ? C7 C8 1.468(5) . ? C7 C10 1.492(5) . ? C8 C9 1.339(5) . ? C8 H8 0.9300 . ? C9 H9 0.9300 . ? C11 C12 1.497(6) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? C13 H13A 0.9600 . ? C13 H13B 0.9600 . ? C13 H13C 0.9600 . ? C15 C16 1.501(5) . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C16 H16A 0.9600 . ? C16 H16B 0.9600 . ? C16 H16C 0.9600 . ? C17 C22 1.393(5) . ? C17 C18 1.396(5) . ? C18 C19 1.394(5) . ? C18 H18 0.9300 . ? C19 C20 1.380(5) . ? C19 H19 0.9300 . ? C20 C21 1.382(5) . ? C21 C22 1.397(5) . ? C21 H21 0.9300 . ? C22 H22 0.9300 . ? 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 C10 O2 C11 117.1(3) . . ? C14 O4 C15 117.8(3) . . ? C1 N1 C9 123.1(3) . . ? C1 N1 N2 113.1(3) . . ? C9 N1 N2 121.3(3) . . ? N1 N2 C3 102.3(2) . . ? N1 N2 C4 110.5(3) . . ? C3 N2 C4 112.0(3) . . ? O6 N3 O7 123.3(4) . . ? O6 N3 C20 118.6(4) . . ? O7 N3 C20 118.0(4) . . ? O1 C1 N1 123.7(4) . . ? O1 C1 C2 128.9(4) . . ? N1 C1 C2 107.4(3) . . ? C1 C2 C3 101.5(3) . . ? C1 C2 H2A 111.5 . . ? C3 C2 H2A 111.5 . . ? C1 C2 H2B 111.5 . . ? C3 C2 H2B 111.5 . . ? H2A C2 H2B 109.3 . . ? N2 C3 C2 105.5(3) . . ? N2 C3 H3A 110.6 . . ? C2 C3 H3A 110.6 . . ? N2 C3 H3B 110.6 . . ? C2 C3 H3B 110.6 . . ? H3A C3 H3B 108.8 . . ? N2 C4 C17 105.8(3) . . ? N2 C4 C5 108.3(3) . . ? C17 C4 C5 114.0(3) . . ? N2 C4 H4 109.5 . . ? C17 C4 H4 109.5 . . ? C5 C4 H4 109.5 . . ? C14 C5 C6 112.8(3) . . ? C14 C5 C4 112.1(3) . . ? C6 C5 C4 112.2(3) . . ? C14 C5 H5 106.4 . . ? C6 C5 H5 106.4 . . ? C4 C5 H5 106.4 . . ? C7 C6 C13 124.2(3) . . ? C7 C6 C5 118.4(3) . . ? C13 C6 C5 117.4(3) . . ? C6 C7 C8 125.4(3) . . ? C6 C7 C10 122.7(3) . . ? C8 C7 C10 111.5(3) . . ? C9 C8 C7 132.0(4) . . ? C9 C8 H8 114.0 . . ? C7 C8 H8 114.0 . . ? C8 C9 N1 128.8(3) . . ? C8 C9 H9 115.6 . . ? N1 C9 H9 115.6 . . ? O3 C10 O2 122.6(4) . . ? O3 C10 C7 124.0(4) . . ? O2 C10 C7 113.3(4) . . ? O2 C11 C12 110.0(3) . . ? O2 C11 H11A 109.7 . . ? C12 C11 H11A 109.7 . . ? O2 C11 H11B 109.7 . . ? C12 C11 H11B 109.7 . . ? H11A C11 H11B 108.2 . . ? C11 C12 H12A 109.5 . . ? C11 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C11 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C6 C13 H13A 109.5 . . ? C6 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C6 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? O5 C14 O4 123.9(3) . . ? O5 C14 C5 126.4(4) . . ? O4 C14 C5 109.7(3) . . ? O4 C15 C16 110.3(3) . . ? O4 C15 H15A 109.6 . . ? C16 C15 H15A 109.6 . . ? O4 C15 H15B 109.6 . . ? C16 C15 H15B 109.6 . . ? H15A C15 H15B 108.1 . . ? C15 C16 H16A 109.5 . . ? C15 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C15 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C22 C17 C18 119.3(4) . . ? C22 C17 C4 121.1(3) . . ? C18 C17 C4 119.5(3) . . ? C19 C18 C17 120.6(4) . . ? C19 C18 H18 119.7 . . ? C17 C18 H18 119.7 . . ? C20 C19 C18 117.9(4) . . ? C20 C19 H19 121.0 . . ? C18 C19 H19 121.0 . . ? C19 C20 C21 123.8(4) . . ? C19 C20 N3 118.8(4) . . ? C21 C20 N3 117.4(4) . . ? C20 C21 C22 117.1(4) . . ? C20 C21 H21 121.5 . . ? C22 C21 H21 121.5 . . ? C17 C22 C21 121.4(4) . . ? C17 C22 H22 119.3 . . ? C21 C22 H22 119.3 . . ? 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 C1 N1 N2 C3 -17.4(4) . . . . ? C9 N1 N2 C3 145.4(3) . . . . ? C1 N1 N2 C4 102.0(3) . . . . ? C9 N1 N2 C4 -95.2(4) . . . . ? C9 N1 C1 O1 12.9(6) . . . . ? N2 N1 C1 O1 175.3(3) . . . . ? C9 N1 C1 C2 -165.0(3) . . . . ? N2 N1 C1 C2 -2.6(4) . . . . ? O1 C1 C2 C3 -157.1(4) . . . . ? N1 C1 C2 C3 20.7(4) . . . . ? N1 N2 C3 C2 29.7(3) . . . . ? C4 N2 C3 C2 -88.6(3) . . . . ? C1 C2 C3 N2 -31.2(4) . . . . ? N1 N2 C4 C17 178.9(3) . . . . ? C3 N2 C4 C17 -67.7(3) . . . . ? N1 N2 C4 C5 56.4(4) . . . . ? C3 N2 C4 C5 169.7(3) . . . . ? N2 C4 C5 C14 -171.6(3) . . . . ? C17 C4 C5 C14 70.9(4) . . . . ? N2 C4 C5 C6 60.3(4) . . . . ? C17 C4 C5 C6 -57.2(4) . . . . ? C14 C5 C6 C7 146.5(3) . . . . ? C4 C5 C6 C7 -85.8(4) . . . . ? C14 C5 C6 C13 -33.9(5) . . . . ? C4 C5 C6 C13 93.9(4) . . . . ? C13 C6 C7 C8 170.6(4) . . . . ? C5 C6 C7 C8 -9.8(6) . . . . ? C13 C6 C7 C10 -2.2(6) . . . . ? C5 C6 C7 C10 177.5(3) . . . . ? C6 C7 C8 C9 43.2(6) . . . . ? C10 C7 C8 C9 -143.3(4) . . . . ? C7 C8 C9 N1 5.2(7) . . . . ? C1 N1 C9 C8 175.6(4) . . . . ? N2 N1 C9 C8 14.6(6) . . . . ? C11 O2 C10 O3 2.8(6) . . . . ? C11 O2 C10 C7 -173.9(3) . . . . ? C6 C7 C10 O3 144.1(4) . . . . ? C8 C7 C10 O3 -29.5(5) . . . . ? C6 C7 C10 O2 -39.2(5) . . . . ? C8 C7 C10 O2 147.2(3) . . . . ? C10 O2 C11 C12 89.1(4) . . . . ? C15 O4 C14 O5 -4.3(5) . . . . ? C15 O4 C14 C5 176.7(3) . . . . ? C6 C5 C14 O5 128.6(4) . . . . ? C4 C5 C14 O5 0.8(5) . . . . ? C6 C5 C14 O4 -52.4(4) . . . . ? C4 C5 C14 O4 179.7(3) . . . . ? C14 O4 C15 C16 -91.9(4) . . . . ? N2 C4 C17 C22 -37.4(4) . . . . ? C5 C4 C17 C22 81.5(4) . . . . ? N2 C4 C17 C18 139.9(3) . . . . ? C5 C4 C17 C18 -101.2(4) . . . . ? C22 C17 C18 C19 -1.6(5) . . . . ? C4 C17 C18 C19 -179.0(3) . . . . ? C17 C18 C19 C20 0.9(6) . . . . ? C18 C19 C20 C21 0.4(6) . . . . ? C18 C19 C20 N3 -179.9(4) . . . . ? O6 N3 C20 C19 167.9(4) . . . . ? O7 N3 C20 C19 -12.1(6) . . . . ? O6 N3 C20 C21 -12.3(6) . . . . ? O7 N3 C20 C21 167.6(4) . . . . ? C19 C20 C21 C22 -1.0(6) . . . . ? N3 C20 C21 C22 179.3(4) . . . . ? C18 C17 C22 C21 1.0(6) . . . . ? C4 C17 C22 C21 178.3(3) . . . . ? C20 C21 C22 C17 0.3(6) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.02 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.234 _refine_diff_density_min -0.270 _refine_diff_density_rms 0.058