# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2009 data_global _journal_name_full Chem.Commun. _journal_coden_cambridge 0182 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_name 'Shengming Ma' _publ_contact_author_email masm@mail.sioc.ac.cn loop_ _publ_author_name 'Shengming Ma' 'Xin Cheng' data_z _database_code_depnum_ccdc_archive 'CCDC 716723' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C33 H33 N3 O6' _chemical_formula_weight 567.62 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 P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 14.1841(4) _cell_length_b 25.4026(7) _cell_length_c 8.5968(2) _cell_angle_alpha 90.00 _cell_angle_beta 107.6040(10) _cell_angle_gamma 90.00 _cell_volume 2952.48(14) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.368 _exptl_crystal_size_mid 0.246 _exptl_crystal_size_min 0.124 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.277 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1200 _exptl_absorpt_coefficient_mu 0.089 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.746088 _exptl_absorpt_correction_T_max 1 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 34090 _diffrn_reflns_av_R_equivalents 0.0295 _diffrn_reflns_av_sigmaI/netI 0.0192 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -30 _diffrn_reflns_limit_k_max 30 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 1.51 _diffrn_reflns_theta_max 25.01 _reflns_number_total 5209 _reflns_number_gt 4031 _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^)+(0.0573P)^2^+0.9374P] 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 5209 _refine_ls_number_parameters 379 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0566 _refine_ls_R_factor_gt 0.0412 _refine_ls_wR_factor_ref 0.1199 _refine_ls_wR_factor_gt 0.1059 _refine_ls_goodness_of_fit_ref 1.020 _refine_ls_restrained_S_all 1.020 _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 -0.18229(13) 0.31652(7) 1.0562(2) 0.0482(4) Uani 1 1 d . . . C2 C -0.20384(16) 0.30310(9) 1.1965(2) 0.0653(6) Uani 1 1 d . . . H2A H -0.1538 0.2971 1.2936 0.078 Uiso 1 1 calc R . . C3 C -0.30242(18) 0.29886(9) 1.1886(3) 0.0716(6) Uani 1 1 d . . . H3A H -0.3190 0.2905 1.2823 0.086 Uiso 1 1 calc R . . C4 C -0.37653(16) 0.30684(9) 1.0440(3) 0.0679(6) Uani 1 1 d . . . H4A H -0.4422 0.3031 1.0412 0.082 Uiso 1 1 calc R . . C5 C -0.35470(15) 0.32017(9) 0.9044(3) 0.0649(6) Uani 1 1 d . . . H5A H -0.4046 0.3257 0.8068 0.078 Uiso 1 1 calc R . . C6 C -0.25649(14) 0.32511(7) 0.9129(2) 0.0512(4) Uani 1 1 d . . . C7 C -0.21090(14) 0.33951(9) 0.7856(2) 0.0586(5) Uani 1 1 d . . . C8 C -0.08591(14) 0.32509(7) 1.0268(2) 0.0497(4) Uani 1 1 d . . . C9 C -0.03691(12) 0.35285(7) 0.7813(2) 0.0455(4) Uani 1 1 d . . . C10 C -0.04270(14) 0.33158(8) 0.6316(2) 0.0528(5) Uani 1 1 d . . . H10A H -0.0901 0.3061 0.5859 0.063 Uiso 1 1 calc R . . C11 C 0.02178(13) 0.34804(7) 0.5491(2) 0.0491(4) Uani 1 1 d . . . H11A H 0.0170 0.3336 0.4475 0.059 Uiso 1 1 calc R . . C12 C 0.09325(12) 0.38550(6) 0.6147(2) 0.0402(4) Uani 1 1 d . . . C13 C 0.10058(13) 0.40506(7) 0.7683(2) 0.0484(4) Uani 1 1 d . . . H13A H 0.1497 0.4294 0.8162 0.058 Uiso 1 1 calc R . . C14 C 0.03621(13) 0.38905(8) 0.8513(2) 0.0507(4) Uani 1 1 d . . . H14A H 0.0421 0.4026 0.9543 0.061 Uiso 1 1 calc R . . C15 C 0.23329(15) 0.54946(7) 0.7786(2) 0.0538(5) Uani 1 1 d . . . C16 C 0.13108(17) 0.55255(9) 0.7299(3) 0.0717(6) Uani 1 1 d . . . H16A H 0.0974 0.5608 0.6220 0.086 Uiso 1 1 calc R . . C17 C 0.07829(18) 0.54368(10) 0.8379(3) 0.0796(7) Uani 1 1 d . . . H17A H 0.0097 0.5465 0.8029 0.096 Uiso 1 1 calc R . . C18 C 0.12615(18) 0.53080(10) 0.9961(3) 0.0742(6) Uani 1 1 d . . . H18A H 0.0904 0.5245 1.0687 0.089 Uiso 1 1 calc R . . C19 C 0.22691(17) 0.52723(10) 1.0472(3) 0.0722(6) Uani 1 1 d . . . H19A H 0.2599 0.5185 1.1550 0.087 Uiso 1 1 calc R . . C20 C 0.27989(16) 0.53659(9) 0.9396(2) 0.0622(5) Uani 1 1 d . . . H20A H 0.3485 0.5342 0.9761 0.075 Uiso 1 1 calc R . . C21 C 0.29173(17) 0.55863(7) 0.6620(3) 0.0613(5) Uani 1 1 d . . . H21A H 0.3604 0.5647 0.7236 0.074 Uiso 1 1 calc R . . H21B H 0.2672 0.5901 0.5986 0.074 Uiso 1 1 calc R . . C22 C 0.28594(15) 0.51205(7) 0.5450(2) 0.0535(5) Uani 1 1 d . . . H22A H 0.2186 0.5091 0.4734 0.064 Uiso 1 1 calc R . . H22B H 0.3282 0.5194 0.4775 0.064 Uiso 1 1 calc R . . C23 C 0.31606(12) 0.46054(7) 0.62938(19) 0.0417(4) Uani 1 1 d . . . C24 C 0.26288(12) 0.41682(6) 0.61618(19) 0.0389(4) Uani 1 1 d . . . C25 C 0.41778(13) 0.45215(7) 0.7494(2) 0.0440(4) Uani 1 1 d . . . H25A H 0.4339 0.4813 0.8277 0.053 Uiso 1 1 calc R . . C26 C 0.33728(12) 0.32673(7) 0.6838(2) 0.0414(4) Uani 1 1 d . . . C27 C 0.17427(18) 0.24199(9) 0.3893(3) 0.0811(7) Uani 1 1 d . . . H27A H 0.1768 0.2062 0.3550 0.122 Uiso 1 1 calc R . . H27B H 0.1599 0.2648 0.2960 0.122 Uiso 1 1 calc R . . H27C H 0.1234 0.2455 0.4412 0.122 Uiso 1 1 calc R . . C28 C 0.27008(16) 0.25656(8) 0.5050(3) 0.0619(5) Uani 1 1 d . . . H28A H 0.2856 0.2334 0.5991 0.074 Uiso 1 1 calc R . . H28B H 0.3219 0.2532 0.4535 0.074 Uiso 1 1 calc R . . C29 C 0.41014(13) 0.40645(7) 0.9955(2) 0.0469(4) Uani 1 1 d . . . C30 C 0.3635(2) 0.36960(10) 1.2147(3) 0.0817(8) Uani 1 1 d . . . H30A H 0.3038 0.3542 1.2280 0.098 Uiso 1 1 calc R . . H30B H 0.3681 0.4056 1.2540 0.098 Uiso 1 1 calc R . . C31 C 0.4503(3) 0.33956(12) 1.3120(3) 0.1006(10) Uani 1 1 d . . . H31A H 0.4527 0.3402 1.4248 0.151 Uiso 1 1 calc R . . H31B H 0.5094 0.3551 1.3004 0.151 Uiso 1 1 calc R . . H31C H 0.4452 0.3038 1.2743 0.151 Uiso 1 1 calc R . . C32 C 0.49856(15) 0.44622(10) 0.6690(3) 0.0658(6) Uani 1 1 d . . . H32A H 0.5610 0.4413 0.7513 0.099 Uiso 1 1 calc R . . H32B H 0.5013 0.4773 0.6072 0.099 Uiso 1 1 calc R . . H32C H 0.4846 0.4163 0.5976 0.099 Uiso 1 1 calc R . . C33 C 0.15801(12) 0.40596(7) 0.5172(2) 0.0444(4) Uani 1 1 d . . . H33A H 0.1582 0.3804 0.4334 0.053 Uiso 1 1 calc R . . H33B H 0.1292 0.4382 0.4627 0.053 Uiso 1 1 calc R . . N1 N -0.10788(10) 0.33817(6) 0.86141(17) 0.0490(4) Uani 1 1 d . . . N2 N 0.31882(9) 0.37717(5) 0.72715(16) 0.0391(3) Uani 1 1 d . . . N3 N 0.40255(10) 0.40343(5) 0.83252(16) 0.0415(3) Uani 1 1 d . . . O1 O -0.25024(11) 0.35058(9) 0.64528(19) 0.0958(6) Uani 1 1 d . . . O2 O -0.00380(10) 0.32190(7) 1.12128(17) 0.0716(4) Uani 1 1 d . . . O3 O 0.35720(11) 0.36954(5) 1.04147(15) 0.0649(4) Uani 1 1 d . . . O4 O 0.46290(11) 0.43791(5) 1.08600(15) 0.0614(4) Uani 1 1 d . . . O5 O 0.26413(9) 0.31057(5) 0.55575(15) 0.0517(3) Uani 1 1 d . . . O6 O 0.40688(10) 0.30062(5) 0.75699(17) 0.0608(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 0.0476(10) 0.0470(10) 0.0489(10) 0.0014(8) 0.0129(8) -0.0003(8) C2 0.0626(13) 0.0816(15) 0.0502(11) 0.0060(10) 0.0150(10) -0.0064(11) C3 0.0732(15) 0.0793(16) 0.0718(14) 0.0026(12) 0.0363(12) -0.0118(12) C4 0.0533(12) 0.0726(15) 0.0836(16) 0.0028(12) 0.0293(12) -0.0053(10) C5 0.0451(11) 0.0758(15) 0.0711(13) 0.0136(11) 0.0134(10) -0.0001(10) C6 0.0457(10) 0.0515(11) 0.0546(11) 0.0065(8) 0.0128(8) 0.0002(8) C7 0.0427(10) 0.0753(14) 0.0529(11) 0.0149(10) 0.0072(9) -0.0012(9) C8 0.0460(10) 0.0538(11) 0.0457(10) 0.0025(8) 0.0084(8) 0.0015(8) C9 0.0397(9) 0.0501(10) 0.0446(9) 0.0038(8) 0.0095(7) 0.0009(8) C10 0.0483(10) 0.0579(12) 0.0482(10) -0.0050(9) 0.0084(8) -0.0166(9) C11 0.0484(10) 0.0561(11) 0.0398(9) -0.0053(8) 0.0087(8) -0.0077(8) C12 0.0342(8) 0.0392(9) 0.0435(9) 0.0018(7) 0.0062(7) 0.0032(7) C13 0.0398(9) 0.0488(10) 0.0546(11) -0.0113(8) 0.0115(8) -0.0049(8) C14 0.0470(10) 0.0559(11) 0.0495(10) -0.0113(9) 0.0153(8) -0.0005(8) C15 0.0624(12) 0.0342(9) 0.0602(12) -0.0021(8) 0.0119(10) 0.0037(8) C16 0.0713(15) 0.0628(14) 0.0695(14) 0.0054(11) 0.0042(12) 0.0198(11) C17 0.0587(14) 0.0850(17) 0.0930(18) -0.0067(14) 0.0195(13) 0.0189(12) C18 0.0719(15) 0.0755(16) 0.0820(16) -0.0121(12) 0.0335(13) 0.0068(12) C19 0.0710(15) 0.0887(17) 0.0554(12) -0.0082(11) 0.0167(11) 0.0087(12) C20 0.0555(12) 0.0724(14) 0.0546(12) -0.0084(10) 0.0103(10) 0.0044(10) C21 0.0785(14) 0.0382(10) 0.0634(12) 0.0081(9) 0.0157(11) -0.0055(9) C22 0.0636(12) 0.0488(11) 0.0481(10) 0.0095(8) 0.0170(9) -0.0068(9) C23 0.0469(10) 0.0415(9) 0.0376(9) -0.0002(7) 0.0142(7) -0.0050(8) C24 0.0415(9) 0.0394(9) 0.0356(8) 0.0004(7) 0.0112(7) -0.0003(7) C25 0.0486(10) 0.0413(9) 0.0418(9) -0.0018(7) 0.0133(8) -0.0128(8) C26 0.0384(9) 0.0391(9) 0.0440(9) -0.0009(7) 0.0086(7) -0.0052(7) C27 0.0746(15) 0.0635(14) 0.0914(17) -0.0326(13) 0.0045(13) -0.0097(12) C28 0.0664(13) 0.0420(11) 0.0692(13) -0.0169(9) 0.0085(10) -0.0018(9) C29 0.0510(10) 0.0409(10) 0.0436(9) 0.0016(8) 0.0065(8) -0.0118(8) C30 0.123(2) 0.0714(15) 0.0494(12) -0.0003(11) 0.0235(13) -0.0402(15) C31 0.140(3) 0.096(2) 0.0648(15) 0.0016(14) 0.0291(17) -0.0300(19) C32 0.0528(12) 0.0874(16) 0.0595(12) 0.0034(11) 0.0206(10) -0.0116(11) C33 0.0415(9) 0.0458(10) 0.0413(9) 0.0036(7) 0.0058(7) 0.0012(8) N1 0.0399(8) 0.0605(10) 0.0444(8) 0.0052(7) 0.0093(6) -0.0019(7) N2 0.0359(7) 0.0365(7) 0.0399(7) -0.0035(6) 0.0039(6) -0.0061(6) N3 0.0399(7) 0.0398(8) 0.0401(7) -0.0023(6) 0.0048(6) -0.0116(6) O1 0.0493(9) 0.1654(18) 0.0635(10) 0.0479(11) 0.0033(7) -0.0064(10) O2 0.0467(8) 0.1077(12) 0.0532(8) 0.0137(8) 0.0043(7) 0.0044(8) O3 0.0870(10) 0.0609(9) 0.0446(7) -0.0020(6) 0.0164(7) -0.0347(8) O4 0.0760(9) 0.0544(8) 0.0447(7) -0.0041(6) 0.0045(6) -0.0274(7) O5 0.0508(7) 0.0398(7) 0.0536(7) -0.0111(5) -0.0007(6) 0.0002(5) O6 0.0497(8) 0.0474(8) 0.0713(9) -0.0048(7) -0.0029(7) 0.0068(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 C2 1.374(3) . ? C1 C6 1.374(3) . ? C1 C8 1.480(3) . ? C2 C3 1.383(3) . ? C2 H2A 0.9300 . ? C3 C4 1.379(3) . ? C3 H3A 0.9300 . ? C4 C5 1.370(3) . ? C4 H4A 0.9300 . ? C5 C6 1.378(3) . ? C5 H5A 0.9300 . ? C6 C7 1.476(3) . ? C7 O1 1.199(2) . ? C7 N1 1.409(2) . ? C8 O2 1.204(2) . ? C8 N1 1.401(2) . ? C9 C10 1.376(3) . ? C9 C14 1.380(3) . ? C9 N1 1.430(2) . ? C10 C11 1.381(3) . ? C10 H10A 0.9300 . ? C11 C12 1.380(2) . ? C11 H11A 0.9300 . ? C12 C13 1.385(2) . ? C12 C33 1.511(2) . ? C13 C14 1.379(3) . ? C13 H13A 0.9300 . ? C14 H14A 0.9300 . ? C15 C20 1.380(3) . ? C15 C16 1.384(3) . ? C15 C21 1.500(3) . ? C16 C17 1.377(3) . ? C16 H16A 0.9300 . ? C17 C18 1.363(3) . ? C17 H17A 0.9300 . ? C18 C19 1.365(3) . ? C18 H18A 0.9300 . ? C19 C20 1.378(3) . ? C19 H19A 0.9300 . ? C20 H20A 0.9300 . ? C21 C22 1.539(3) . ? C21 H21A 0.9700 . ? C21 H21B 0.9700 . ? C22 C23 1.494(2) . ? C22 H22A 0.9700 . ? C22 H22B 0.9700 . ? C23 C24 1.328(2) . ? C23 C25 1.514(2) . ? C24 N2 1.448(2) . ? C24 C33 1.499(2) . ? C25 N3 1.477(2) . ? C25 C32 1.514(3) . ? C25 H25A 0.9800 . ? C26 O6 1.198(2) . ? C26 O5 1.329(2) . ? C26 N2 1.381(2) . ? C27 C28 1.468(3) . ? C27 H27A 0.9600 . ? C27 H27B 0.9600 . ? C27 H27C 0.9600 . ? C28 O5 1.450(2) . ? C28 H28A 0.9700 . ? C28 H28B 0.9700 . ? C29 O4 1.205(2) . ? C29 O3 1.334(2) . ? C29 N3 1.375(2) . ? C30 O3 1.465(2) . ? C30 C31 1.475(4) . ? C30 H30A 0.9700 . ? C30 H30B 0.9700 . ? C31 H31A 0.9600 . ? C31 H31B 0.9600 . ? C31 H31C 0.9600 . ? C32 H32A 0.9600 . ? C32 H32B 0.9600 . ? C32 H32C 0.9600 . ? C33 H33A 0.9700 . ? C33 H33B 0.9700 . ? N2 N3 1.4231(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 C2 C1 C6 120.86(18) . . ? C2 C1 C8 130.45(17) . . ? C6 C1 C8 108.68(16) . . ? C1 C2 C3 117.8(2) . . ? C1 C2 H2A 121.1 . . ? C3 C2 H2A 121.1 . . ? C4 C3 C2 121.1(2) . . ? C4 C3 H3A 119.4 . . ? C2 C3 H3A 119.4 . . ? C5 C4 C3 120.9(2) . . ? C5 C4 H4A 119.5 . . ? C3 C4 H4A 119.5 . . ? C4 C5 C6 117.9(2) . . ? C4 C5 H5A 121.0 . . ? C6 C5 H5A 121.0 . . ? C1 C6 C5 121.39(19) . . ? C1 C6 C7 108.41(16) . . ? C5 C6 C7 130.20(18) . . ? O1 C7 N1 124.97(19) . . ? O1 C7 C6 128.99(18) . . ? N1 C7 C6 106.05(15) . . ? O2 C8 N1 124.98(17) . . ? O2 C8 C1 129.06(17) . . ? N1 C8 C1 105.96(15) . . ? C10 C9 C14 119.59(17) . . ? C10 C9 N1 119.78(16) . . ? C14 C9 N1 120.62(16) . . ? C9 C10 C11 120.03(17) . . ? C9 C10 H10A 120.0 . . ? C11 C10 H10A 120.0 . . ? C12 C11 C10 121.16(17) . . ? C12 C11 H11A 119.4 . . ? C10 C11 H11A 119.4 . . ? C11 C12 C13 118.10(16) . . ? C11 C12 C33 120.33(15) . . ? C13 C12 C33 121.51(15) . . ? C14 C13 C12 121.13(16) . . ? C14 C13 H13A 119.4 . . ? C12 C13 H13A 119.4 . . ? C13 C14 C9 119.90(17) . . ? C13 C14 H14A 120.0 . . ? C9 C14 H14A 120.0 . . ? C20 C15 C16 117.2(2) . . ? C20 C15 C21 120.86(19) . . ? C16 C15 C21 121.94(19) . . ? C17 C16 C15 121.4(2) . . ? C17 C16 H16A 119.3 . . ? C15 C16 H16A 119.3 . . ? C18 C17 C16 120.3(2) . . ? C18 C17 H17A 119.9 . . ? C16 C17 H17A 119.9 . . ? C17 C18 C19 119.6(2) . . ? C17 C18 H18A 120.2 . . ? C19 C18 H18A 120.2 . . ? C18 C19 C20 120.2(2) . . ? C18 C19 H19A 119.9 . . ? C20 C19 H19A 119.9 . . ? C19 C20 C15 121.4(2) . . ? C19 C20 H20A 119.3 . . ? C15 C20 H20A 119.3 . . ? C15 C21 C22 112.73(16) . . ? C15 C21 H21A 109.0 . . ? C22 C21 H21A 109.0 . . ? C15 C21 H21B 109.0 . . ? C22 C21 H21B 109.0 . . ? H21A C21 H21B 107.8 . . ? C23 C22 C21 113.88(15) . . ? C23 C22 H22A 108.8 . . ? C21 C22 H22A 108.8 . . ? C23 C22 H22B 108.8 . . ? C21 C22 H22B 108.8 . . ? H22A C22 H22B 107.7 . . ? C24 C23 C22 128.25(16) . . ? C24 C23 C25 109.89(14) . . ? C22 C23 C25 121.86(15) . . ? C23 C24 N2 109.98(14) . . ? C23 C24 C33 130.01(15) . . ? N2 C24 C33 119.86(14) . . ? N3 C25 C23 101.48(13) . . ? N3 C25 C32 112.28(16) . . ? C23 C25 C32 113.59(15) . . ? N3 C25 H25A 109.7 . . ? C23 C25 H25A 109.7 . . ? C32 C25 H25A 109.7 . . ? O6 C26 O5 125.25(16) . . ? O6 C26 N2 124.41(15) . . ? O5 C26 N2 110.23(14) . . ? C28 C27 H27A 109.5 . . ? C28 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? C28 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? O5 C28 C27 108.43(17) . . ? O5 C28 H28A 110.0 . . ? C27 C28 H28A 110.0 . . ? O5 C28 H28B 110.0 . . ? C27 C28 H28B 110.0 . . ? H28A C28 H28B 108.4 . . ? O4 C29 O3 124.79(16) . . ? O4 C29 N3 122.47(16) . . ? O3 C29 N3 112.65(14) . . ? O3 C30 C31 111.1(2) . . ? O3 C30 H30A 109.4 . . ? C31 C30 H30A 109.4 . . ? O3 C30 H30B 109.4 . . ? C31 C30 H30B 109.4 . . ? H30A C30 H30B 108.0 . . ? C30 C31 H31A 109.5 . . ? C30 C31 H31B 109.5 . . ? H31A C31 H31B 109.5 . . ? C30 C31 H31C 109.5 . . ? H31A C31 H31C 109.5 . . ? H31B C31 H31C 109.5 . . ? C25 C32 H32A 109.5 . . ? C25 C32 H32B 109.5 . . ? H32A C32 H32B 109.5 . . ? C25 C32 H32C 109.5 . . ? H32A C32 H32C 109.5 . . ? H32B C32 H32C 109.5 . . ? C24 C33 C12 114.43(14) . . ? C24 C33 H33A 108.7 . . ? C12 C33 H33A 108.7 . . ? C24 C33 H33B 108.7 . . ? C12 C33 H33B 108.7 . . ? H33A C33 H33B 107.6 . . ? C8 N1 C7 110.90(15) . . ? C8 N1 C9 125.30(14) . . ? C7 N1 C9 123.59(15) . . ? C26 N2 N3 114.63(13) . . ? C26 N2 C24 125.33(13) . . ? N3 N2 C24 106.18(12) . . ? C29 N3 N2 117.90(13) . . ? C29 N3 C25 117.95(13) . . ? N2 N3 C25 107.50(12) . . ? C29 O3 C30 115.72(15) . . ? C26 O5 C28 116.07(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 C6 C1 C2 C3 -0.3(3) . . . . ? C8 C1 C2 C3 178.6(2) . . . . ? C1 C2 C3 C4 1.2(4) . . . . ? C2 C3 C4 C5 -1.2(4) . . . . ? C3 C4 C5 C6 0.3(3) . . . . ? C2 C1 C6 C5 -0.6(3) . . . . ? C8 C1 C6 C5 -179.68(19) . . . . ? C2 C1 C6 C7 179.15(19) . . . . ? C8 C1 C6 C7 0.0(2) . . . . ? C4 C5 C6 C1 0.6(3) . . . . ? C4 C5 C6 C7 -179.1(2) . . . . ? C1 C6 C7 O1 -179.0(2) . . . . ? C5 C6 C7 O1 0.6(4) . . . . ? C1 C6 C7 N1 0.7(2) . . . . ? C5 C6 C7 N1 -179.6(2) . . . . ? C2 C1 C8 O2 0.3(4) . . . . ? C6 C1 C8 O2 179.3(2) . . . . ? C2 C1 C8 N1 -179.8(2) . . . . ? C6 C1 C8 N1 -0.7(2) . . . . ? C14 C9 C10 C11 -2.7(3) . . . . ? N1 C9 C10 C11 175.99(17) . . . . ? C9 C10 C11 C12 0.5(3) . . . . ? C10 C11 C12 C13 1.9(3) . . . . ? C10 C11 C12 C33 -175.38(17) . . . . ? C11 C12 C13 C14 -2.2(3) . . . . ? C33 C12 C13 C14 175.04(16) . . . . ? C12 C13 C14 C9 0.1(3) . . . . ? C10 C9 C14 C13 2.4(3) . . . . ? N1 C9 C14 C13 -176.28(16) . . . . ? C20 C15 C16 C17 0.6(3) . . . . ? C21 C15 C16 C17 179.5(2) . . . . ? C15 C16 C17 C18 -1.0(4) . . . . ? C16 C17 C18 C19 0.6(4) . . . . ? C17 C18 C19 C20 0.0(4) . . . . ? C18 C19 C20 C15 -0.3(4) . . . . ? C16 C15 C20 C19 0.0(3) . . . . ? C21 C15 C20 C19 -178.93(19) . . . . ? C20 C15 C21 C22 103.9(2) . . . . ? C16 C15 C21 C22 -75.0(2) . . . . ? C15 C21 C22 C23 -55.1(2) . . . . ? C21 C22 C23 C24 120.5(2) . . . . ? C21 C22 C23 C25 -58.8(2) . . . . ? C22 C23 C24 N2 -176.53(16) . . . . ? C25 C23 C24 N2 2.87(19) . . . . ? C22 C23 C24 C33 -1.2(3) . . . . ? C25 C23 C24 C33 178.25(16) . . . . ? C24 C23 C25 N3 -15.21(18) . . . . ? C22 C23 C25 N3 164.24(15) . . . . ? C24 C23 C25 C32 105.51(18) . . . . ? C22 C23 C25 C32 -75.0(2) . . . . ? C23 C24 C33 C12 -124.93(19) . . . . ? N2 C24 C33 C12 50.1(2) . . . . ? C11 C12 C33 C24 -143.28(17) . . . . ? C13 C12 C33 C24 39.5(2) . . . . ? O2 C8 N1 C7 -178.9(2) . . . . ? C1 C8 N1 C7 1.2(2) . . . . ? O2 C8 N1 C9 -4.0(3) . . . . ? C1 C8 N1 C9 176.06(16) . . . . ? O1 C7 N1 C8 178.6(2) . . . . ? C6 C7 N1 C8 -1.2(2) . . . . ? O1 C7 N1 C9 3.6(3) . . . . ? C6 C7 N1 C9 -176.14(17) . . . . ? C10 C9 N1 C8 135.12(19) . . . . ? C14 C9 N1 C8 -46.2(3) . . . . ? C10 C9 N1 C7 -50.6(3) . . . . ? C14 C9 N1 C7 128.0(2) . . . . ? O6 C26 N2 N3 19.5(2) . . . . ? O5 C26 N2 N3 -164.06(13) . . . . ? O6 C26 N2 C24 153.98(17) . . . . ? O5 C26 N2 C24 -29.6(2) . . . . ? C23 C24 N2 C26 -126.12(17) . . . . ? C33 C24 N2 C26 58.0(2) . . . . ? C23 C24 N2 N3 11.40(18) . . . . ? C33 C24 N2 N3 -164.51(14) . . . . ? O4 C29 N3 N2 -161.35(17) . . . . ? O3 C29 N3 N2 21.7(2) . . . . ? O4 C29 N3 C25 -29.6(3) . . . . ? O3 C29 N3 C25 153.50(16) . . . . ? C26 N2 N3 C29 -102.15(18) . . . . ? C24 N2 N3 C29 115.16(16) . . . . ? C26 N2 N3 C25 121.55(15) . . . . ? C24 N2 N3 C25 -21.15(16) . . . . ? C23 C25 N3 C29 -114.44(16) . . . . ? C32 C25 N3 C29 123.93(17) . . . . ? C23 C25 N3 N2 21.84(16) . . . . ? C32 C25 N3 N2 -99.79(16) . . . . ? O4 C29 O3 C30 1.9(3) . . . . ? N3 C29 O3 C30 178.70(19) . . . . ? C31 C30 O3 C29 -85.0(2) . . . . ? O6 C26 O5 C28 1.1(3) . . . . ? N2 C26 O5 C28 -175.27(15) . . . . ? C27 C28 O5 C26 167.20(18) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.01 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.439 _refine_diff_density_min -0.326 _refine_diff_density_rms 0.033