Supplementary Material (ESI) for Chemical Communications This journal is (c) The Royal Society of Chemistry 2004 data_global _journal_coden_Cambridge 182 loop_ _publ_author_name 'Philip Coppens' 'Bao-Qing Ma' _publ_contact_author_name 'Prof Philip Coppens' _publ_contact_author_address ; Chemistry 732 NSC, SUNY at Buffalo Buffalo New York 14260 UNITED STATES OF AMERICA ; _publ_contact_author_email COPPENS@ACSU.BUFFALO.EDU _publ_requested_journal 'Chemical Communications' _publ_section_title ; Symmetry induced supramolecular assembly of a resorcinarene trimeric molecular box ; data_p63m_a _database_code_depnum_ccdc_archive 'CCDC 230024' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C168 H172 N12 O26' _chemical_formula_weight 2775.18 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 Hexagonal _symmetry_space_group_name_H-M P6(3)/m loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z' '-x+y, -x, z' '-x, -y, z+1/2' 'y, -x+y, z+1/2' 'x-y, x, z+1/2' '-x, -y, -z' 'y, -x+y, -z' 'x-y, x, -z' 'x, y, -z-1/2' '-y, x-y, -z-1/2' '-x+y, -x, -z-1/2' _cell_length_a 22.9483(11) _cell_length_b 22.9483(11) _cell_length_c 16.1980(12) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 7387.4(7) _cell_formula_units_Z 2 _cell_measurement_temperature 90(1) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prismatic _exptl_crystal_colour yellow _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.248 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2944 _exptl_absorpt_coefficient_mu 0.084 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 90(1) _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 'SMART CCD 1000' _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 54639 _diffrn_reflns_av_R_equivalents 0.1198 _diffrn_reflns_av_sigmaI/netI 0.0568 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 1.02 _diffrn_reflns_theta_max 31.04 _reflns_number_total 4195 _reflns_number_gt 2620 _reflns_threshold_expression >2sigma(I) _computing_data_collection SMART _computing_cell_refinement SMART _computing_data_reduction SAINT _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics XP _computing_publication_material XCIF _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^)+(0.1204P)^2^+0.8922P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0146(4) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 4195 _refine_ls_number_parameters 447 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1096 _refine_ls_R_factor_gt 0.0656 _refine_ls_wR_factor_ref 0.1962 _refine_ls_wR_factor_gt 0.1676 _refine_ls_goodness_of_fit_ref 1.070 _refine_ls_restrained_S_all 1.070 _refine_ls_shift/su_max 0.181 _refine_ls_shift/su_mean 0.001 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N1 N 0.30093(4) 0.40958(4) 0.37413(6) 0.0265(3) Uani 1 1 d . . . N2 N 0.38830(4) 0.65857(4) 0.35975(5) 0.0198(3) Uani 1 1 d . . . O1 O 0.28717(4) 0.28761(3) 0.39830(5) 0.0297(3) Uani 1 1 d . . . O2 O 0.41035(4) 0.29561(3) 0.43204(5) 0.0291(3) Uani 1 1 d . . . O3 O 0.55433(3) 0.20498(4) 0.43568(5) 0.0297(3) Uani 1 1 d . . . O4 O 0.57919(4) 0.08816(5) 0.39897(5) 0.0592(4) Uani 1 1 d . . . O5 O 0.3333 0.6667 0.54133(8) 0.0340(4) Uani 1 3 d S . . C1 C 0.28306(7) 0.28667(7) 0.2500 0.0238(5) Uani 1 2 d S . . C2 C 0.28393(5) 0.25689(5) 0.32414(7) 0.0236(4) Uani 1 1 d . . . C3 C 0.28463(5) 0.19658(5) 0.32570(7) 0.0235(4) Uani 1 1 d . . . C4 C 0.28520(7) 0.16805(7) 0.2500 0.0248(5) Uani 1 2 d S . . C5 C 0.28947(5) 0.16537(5) 0.40695(7) 0.0269(4) Uani 1 1 d . . . C6 C 0.23228(6) 0.09343(6) 0.41733(8) 0.0379(4) Uani 1 1 d . . . C7 C 0.16385(7) 0.08954(7) 0.42120(11) 0.0592(6) Uani 1 1 d . . . C8 C 0.35962(5) 0.17476(5) 0.41551(6) 0.0219(3) Uani 1 1 d . . . C9 C 0.41553(5) 0.23827(5) 0.42642(6) 0.0223(3) Uani 1 1 d . . . C10 C 0.47961(5) 0.24777(5) 0.43239(6) 0.0237(4) Uani 1 1 d . . . C11 C 0.49012(5) 0.19371(5) 0.42710(6) 0.0228(4) Uani 1 1 d . . . C12 C 0.43601(5) 0.12869(5) 0.41484(6) 0.0212(3) Uani 1 1 d . . . C13 C 0.37242(5) 0.12151(5) 0.40993(6) 0.0213(4) Uani 1 1 d . . . C14 C 0.44879(5) 0.07019(5) 0.40597(6) 0.0217(3) Uani 1 1 d . . . C15 C 0.38609(5) 0.00140(5) 0.41264(7) 0.0259(4) Uani 1 1 d . . . C16 C 0.40063(6) -0.05602(6) 0.40522(7) 0.0312(4) Uani 1 1 d . . . C17 C 0.48637(5) 0.07652(5) 0.32514(6) 0.0200(3) Uani 1 1 d . . . C18 C 0.45644(7) 0.07428(7) 0.2500 0.0184(5) Uani 1 2 d S . . C19 C 0.54972(5) 0.08362(6) 0.32359(7) 0.0272(4) Uani 1 1 d . . . C20 C 0.58215(7) 0.08723(8) 0.2500 0.0276(6) Uani 1 2 d S . . C21 C 0.36168(5) 0.46462(6) 0.37236(7) 0.0308(4) Uani 1 1 d . . . C22 C 0.37159(5) 0.52887(5) 0.36650(7) 0.0263(4) Uani 1 1 d . . . C23 C 0.31627(5) 0.53789(5) 0.36255(6) 0.0201(3) Uani 1 1 d . . . C24 C 0.25291(5) 0.48085(5) 0.36316(7) 0.0258(4) Uani 1 1 d . . . C25 C 0.24812(6) 0.41859(5) 0.36936(7) 0.0303(4) Uani 1 1 d . . . C26 C 0.32551(5) 0.60646(5) 0.36021(6) 0.0171(3) Uani 1 1 d . . . C27 C 0.09397(11) -0.11136(12) 0.2500 0.0721(10) Uani 1 2 d S . . C28 C 0.12648(8) -0.09944(8) 0.32433(11) 0.0654(6) Uani 1 1 d . . . C29 C 0.19651(8) -0.07334(7) 0.32387(11) 0.0598(6) Uani 1 1 d . . . C30 C 0.22987(10) -0.06119(11) 0.2500 0.0591(9) Uani 1 2 d S . . C31 C 0.38621(8) 0.73244(8) 0.7500 0.0315(6) Uani 1 2 d S . . C32 C 0.39843(8) 0.67919(9) 0.7500 0.0320(6) Uani 1 2 d S . . H18A H 0.4106(5) 0.0680(5) 0.2500 0.000(3) Uiso 1 2 d S . . H4A H 0.2868(7) 0.1259(7) 0.2500 0.025(4) Uiso 1 2 d S . . H5A H 0.2741(4) 0.1838(4) 0.4597(6) 0.016(3) Uiso 1 1 d . . . H15B H 0.3545(5) -0.0044(5) 0.3703(6) 0.026(3) Uiso 1 1 d . . . H15A H 0.3634(5) -0.0020(5) 0.4647(7) 0.031(3) Uiso 1 1 d . . . H1A H 0.2861(6) 0.3295(6) 0.2500 0.015(4) Uiso 1 2 d S . . H14A H 0.4780(5) 0.0706(5) 0.4489(6) 0.026(3) Uiso 1 1 d . . . H7C H 0.1513(7) 0.1085(8) 0.3561(10) 0.096(6) Uiso 1 1 d . . . H6A H 0.2399(6) 0.0724(6) 0.4777(8) 0.055(4) Uiso 1 1 d . . . H16C H 0.4351(5) -0.0479(5) 0.4478(7) 0.041(4) Uiso 1 1 d . . . H16B H 0.4185(5) -0.0551(5) 0.3491(7) 0.031(3) Uiso 1 1 d . . . H13A H 0.3351(5) 0.0763(5) 0.4030(6) 0.029(3) Uiso 1 1 d . . . H7B H 0.1147(10) 0.0298(9) 0.4159(13) 0.126(8) Uiso 1 1 d . . . H20A H 0.6284(7) 0.0964(7) 0.2500 0.027(4) Uiso 1 2 d S . . H21A H 0.3987(5) 0.4539(5) 0.3756(7) 0.033(3) Uiso 1 1 d . . . H16A H 0.3578(5) -0.1003(5) 0.4131(7) 0.025(3) Uiso 1 1 d . . . H7A H 0.1716(6) 0.1223(6) 0.4743(8) 0.059(4) Uiso 1 1 d . . . H10A H 0.5160(4) 0.2891(4) 0.4396(5) 0.009(2) Uiso 1 1 d . . . H22A H 0.4165(5) 0.5686(5) 0.3647(7) 0.040(3) Uiso 1 1 d . . . H25A H 0.2022(5) 0.3764(5) 0.3721(7) 0.035(3) Uiso 1 1 d . . . H6B H 0.2384(6) 0.0619(6) 0.3681(8) 0.057(4) Uiso 1 1 d . . . H24A H 0.2126(5) 0.4881(6) 0.3590(8) 0.044(4) Uiso 1 1 d . . . H30A H 0.2814(9) -0.0402(9) 0.2500 0.064(6) Uiso 1 2 d S . . H29A H 0.2220(6) -0.0649(6) 0.3818(8) 0.050(4) Uiso 1 1 d . . . H28A H 0.1010(7) -0.1138(7) 0.3852(9) 0.080(5) Uiso 1 1 d . . . H27A H 0.0425(12) -0.1261(12) 0.2500 0.112(9) Uiso 1 2 d S . . H32A H 0.4420(8) 0.6851(8) 0.7500 0.036(5) Uiso 1 2 d S . . H2 H 0.3737(6) 0.2871(5) 0.4274(7) 0.038(4) Uiso 1 1 d . . . H1 H 0.2890(7) 0.3356(7) 0.3900(9) 0.075(5) Uiso 1 1 d . . . H4 H 0.6347(7) 0.1031(8) 0.4005(11) 0.092(6) Uiso 1 1 d . . . H31A H 0.4198(8) 0.7789(8) 0.7500 0.046(5) Uiso 1 2 d S . . H5 H 0.2955(9) 0.6685(11) 0.5636(14) 0.078(8) Uiso 0.67 1 d P . . H3 H 0.5601(9) 0.1808(9) 0.4246(12) 0.113(7) Uiso 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 N1 0.0292(4) 0.0249(4) 0.0323(5) -0.0027(4) 0.0035(4) 0.0186(3) N2 0.0177(4) 0.0193(4) 0.0208(4) 0.0011(3) 0.0020(3) 0.0081(3) O1 0.0390(4) 0.0212(3) 0.0327(4) -0.0007(3) 0.0037(3) 0.0179(3) O2 0.0279(4) 0.0178(3) 0.0413(4) -0.0007(3) 0.0019(3) 0.0112(3) O3 0.0194(4) 0.0333(4) 0.0329(4) 0.0051(3) -0.0008(3) 0.0106(3) O4 0.0309(4) 0.1179(7) 0.0320(4) 0.0190(4) 0.0010(3) 0.0395(4) O5 0.0374(5) 0.0374(5) 0.0271(6) 0.000 0.000 0.0187(3) C1 0.0260(7) 0.0124(7) 0.0375(8) 0.000 0.000 0.0130(5) C2 0.0234(5) 0.0156(5) 0.0320(5) -0.0021(4) 0.0006(4) 0.0099(4) C3 0.0190(5) 0.0145(5) 0.0352(6) 0.0037(4) 0.0029(4) 0.0071(4) C4 0.0180(7) 0.0145(7) 0.0400(8) 0.000 0.000 0.0066(5) C5 0.0248(5) 0.0209(5) 0.0359(6) 0.0080(4) 0.0066(4) 0.0122(4) C6 0.0265(6) 0.0345(6) 0.0544(7) 0.0109(5) 0.0071(5) 0.0164(4) C7 0.0383(7) 0.0557(8) 0.0880(11) 0.0258(7) 0.0152(7) 0.0268(5) C8 0.0231(5) 0.0183(5) 0.0249(5) 0.0044(4) 0.0037(4) 0.0108(4) C9 0.0271(5) 0.0171(5) 0.0244(5) 0.0025(4) 0.0020(4) 0.0124(4) C10 0.0240(6) 0.0151(5) 0.0249(5) 0.0013(4) 0.0010(4) 0.0045(4) C11 0.0220(5) 0.0253(5) 0.0207(5) 0.0008(4) -0.0011(4) 0.0116(4) C12 0.0214(5) 0.0214(5) 0.0176(4) 0.0053(4) 0.0030(4) 0.0083(4) C13 0.0226(5) 0.0194(5) 0.0198(4) 0.0014(4) 0.0003(4) 0.0089(4) C14 0.0241(5) 0.0209(5) 0.0232(5) 0.0021(4) -0.0002(4) 0.0137(4) C15 0.0252(5) 0.0210(5) 0.0308(5) 0.0052(4) 0.0053(4) 0.0110(4) C16 0.0332(6) 0.0205(6) 0.0374(6) 0.0061(5) 0.0055(5) 0.0116(4) C17 0.0172(5) 0.0134(5) 0.0290(5) 0.0027(4) 0.0020(4) 0.0074(4) C18 0.0154(6) 0.0163(7) 0.0265(7) 0.000 0.000 0.0103(5) C19 0.0232(5) 0.0290(5) 0.0284(5) 0.0025(4) -0.0030(4) 0.0122(4) C20 0.0107(7) 0.0286(8) 0.0413(9) 0.000 0.000 0.0081(6) C21 0.0276(5) 0.0301(6) 0.0395(6) -0.0031(5) 0.0004(5) 0.0179(4) C22 0.0226(5) 0.0172(5) 0.0402(6) -0.0011(4) 0.0034(5) 0.0108(4) C23 0.0221(5) 0.0213(5) 0.0186(4) -0.0028(4) 0.0000(4) 0.0120(4) C24 0.0208(5) 0.0187(5) 0.0335(5) -0.0035(4) 0.0008(5) 0.0066(4) C25 0.0315(6) 0.0148(5) 0.0383(6) -0.0039(4) 0.0020(5) 0.0068(4) C26 0.0164(5) 0.0197(5) 0.0177(4) -0.0009(4) 0.0008(4) 0.0109(3) C27 0.0582(13) 0.0616(13) 0.0928(18) 0.000 0.000 0.0270(10) C28 0.0596(9) 0.0495(8) 0.0843(11) 0.0075(8) 0.0202(8) 0.0250(6) C29 0.0554(8) 0.0426(8) 0.0745(11) 0.0030(7) 0.0049(8) 0.0194(6) C30 0.0367(11) 0.0512(12) 0.0745(15) 0.000 0.000 0.0108(9) C31 0.0344(8) 0.0286(9) 0.0212(7) 0.000 0.000 0.0080(7) C32 0.0308(8) 0.0423(9) 0.0230(7) 0.000 0.000 0.0184(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 N1 C25 1.3298(18) . ? N1 C21 1.3336(12) . ? N2 C26 1.3317(15) 2_665 ? N2 C26 1.3354(11) . ? O1 C2 1.3761(13) . ? O2 C9 1.3822(16) . ? O3 C11 1.3699(15) . ? O4 C19 1.3742(14) . ? C1 C2 1.3868(14) 10_556 ? C1 C2 1.3868(14) . ? C2 C3 1.3922(19) . ? C3 C4 1.3932(14) . ? C3 C5 1.5286(17) . ? C4 C3 1.3932(14) 10_556 ? C5 C6 1.5198(14) . ? C5 C8 1.5198(18) . ? C6 C7 1.529(2) . ? C8 C9 1.3898(12) . ? C8 C13 1.3952(19) . ? C9 C10 1.3780(18) . ? C10 C11 1.3797(19) . ? C11 C12 1.3982(13) . ? C12 C13 1.3867(17) . ? C12 C14 1.5176(19) . ? C14 C15 1.5175(13) . ? C14 C17 1.5341(15) . ? C15 C16 1.517(2) . ? C17 C19 1.3798(18) . ? C17 C18 1.3859(13) . ? C18 C17 1.3859(13) 10_556 ? C19 C20 1.3856(14) . ? C20 C19 1.3856(14) 10_556 ? C21 C22 1.3783(18) . ? C22 C23 1.3861(18) . ? C23 C24 1.3873(12) . ? C23 C26 1.4795(16) . ? C24 C25 1.3808(18) . ? C26 N2 1.3317(15) 3_565 ? C27 C28 1.370(2) 10_556 ? C27 C28 1.370(2) . ? C28 C29 1.407(2) . ? C29 C30 1.372(2) . ? C30 C29 1.372(2) 10_556 ? C31 C32 1.375(2) 2_665 ? C31 C32 1.384(3) . ? C32 C31 1.375(2) 3_565 ? 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 C25 N1 C21 117.00(11) . . ? C26 N2 C26 115.34(11) 2_665 . ? C2 C1 C2 119.97(17) 10_556 . ? O1 C2 C1 120.92(12) . . ? O1 C2 C3 117.97(10) . . ? C1 C2 C3 121.05(11) . . ? C2 C3 C4 117.30(11) . . ? C2 C3 C5 121.40(10) . . ? C4 C3 C5 121.17(12) . . ? C3 C4 C3 123.31(17) . 10_556 ? C6 C5 C8 114.96(11) . . ? C6 C5 C3 112.25(9) . . ? C8 C5 C3 109.39(9) . . ? C5 C6 C7 111.82(12) . . ? C9 C8 C13 116.00(11) . . ? C9 C8 C5 121.15(12) . . ? C13 C8 C5 122.81(8) . . ? C10 C9 O2 115.96(8) . . ? C10 C9 C8 121.83(12) . . ? O2 C9 C8 122.20(11) . . ? C9 C10 C11 120.39(9) . . ? O3 C11 C10 118.63(8) . . ? O3 C11 C12 120.88(12) . . ? C10 C11 C12 120.48(11) . . ? C13 C12 C11 117.08(12) . . ? C13 C12 C14 123.16(8) . . ? C11 C12 C14 119.75(11) . . ? C12 C13 C8 124.21(9) . . ? C15 C14 C12 114.29(10) . . ? C15 C14 C17 110.80(9) . . ? C12 C14 C17 110.19(9) . . ? C16 C15 C14 113.07(10) . . ? C19 C17 C18 117.50(11) . . ? C19 C17 C14 122.40(10) . . ? C18 C17 C14 120.09(11) . . ? C17 C18 C17 122.87(15) 10_556 . ? O4 C19 C17 116.25(10) . . ? O4 C19 C20 122.04(12) . . ? C17 C19 C20 121.69(11) . . ? C19 C20 C19 118.70(16) . 10_556 ? N1 C21 C22 123.36(12) . . ? C21 C22 C23 119.30(9) . . ? C22 C23 C24 117.70(11) . . ? C22 C23 C26 120.34(8) . . ? C24 C23 C26 121.93(11) . . ? C25 C24 C23 118.72(12) . . ? N1 C25 C24 123.91(9) . . ? N2 C26 N2 124.65(11) 3_565 . ? N2 C26 C23 117.36(8) 3_565 . ? N2 C26 C23 117.99(10) . . ? C28 C27 C28 123.0(2) 10_556 . ? C27 C28 C29 118.19(17) . . ? C30 C29 C28 119.59(16) . . ? C29 C30 C29 121.4(2) . 10_556 ? C32 C31 C32 119.11(17) 2_665 . ? C31 C32 C31 120.89(17) 3_565 . ? _diffrn_measured_fraction_theta_max 0.515 _diffrn_reflns_theta_full 31.04 _diffrn_measured_fraction_theta_full 0.515 _refine_diff_density_max 0.800 _refine_diff_density_min -0.498 _refine_diff_density_rms 0.162 data_p63m_b _database_code_depnum_ccdc_archive 'CCDC 230025' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C176 H188 N12 O26' _chemical_formula_weight 2887.38 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 hexagonal _symmetry_space_group_name_H-M P63/m loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z' '-x+y, -x, z' '-x, -y, z+1/2' 'y, -x+y, z+1/2' 'x-y, x, z+1/2' '-x, -y, -z' 'y, -x+y, -z' 'x-y, x, -z' 'x, y, -z-1/2' '-y, x-y, -z-1/2' '-x+y, -x, -z-1/2' _cell_length_a 22.9898(10) _cell_length_b 22.9898(10) _cell_length_c 16.4458(10) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 7527.6(7) _cell_formula_units_Z 2 _cell_measurement_temperature 90(1) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prismatic _exptl_crystal_colour yellow _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.274 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 3072 _exptl_absorpt_coefficient_mu 0.086 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 90(1) _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 'SMART CCD 1000' _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 89657 _diffrn_reflns_av_R_equivalents 0.1729 _diffrn_reflns_av_sigmaI/netI 0.1552 _diffrn_reflns_limit_h_min -30 _diffrn_reflns_limit_h_max 30 _diffrn_reflns_limit_k_min -32 _diffrn_reflns_limit_k_max 32 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 1.02 _diffrn_reflns_theta_max 31.09 _reflns_number_total 7915 _reflns_number_gt 3146 _reflns_threshold_expression >2sigma(I) _computing_data_collection SMART _computing_cell_refinement SMART _computing_data_reduction SAINT _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics XP _computing_publication_material XCIF _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^)+(0.1661P)^2^+1.4605P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.031(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 7915 _refine_ls_number_parameters 477 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.2297 _refine_ls_R_factor_gt 0.0914 _refine_ls_wR_factor_ref 0.3206 _refine_ls_wR_factor_gt 0.2247 _refine_ls_goodness_of_fit_ref 1.022 _refine_ls_restrained_S_all 1.022 _refine_ls_shift/su_max 0.686 _refine_ls_shift/su_mean 0.015 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 0.69421(14) 0.10625(13) 0.37288(19) 0.0371(7) Uani 1 1 d . . . N2 N 0.61094(12) 0.27065(12) 0.35876(17) 0.0281(6) Uani 1 1 d . . . C1 C 0.7132(2) -0.2848(2) 0.7500 0.0334(11) Uani 1 2 d S . . C2 C 0.74238(15) -0.28582(16) 0.6770(2) 0.0332(8) Uani 1 1 d . . . C3 C 0.80341(14) -0.28614(15) 0.6755(2) 0.0315(7) Uani 1 1 d . . . C4 C 0.8314(2) -0.2867(2) 0.7500 0.0327(11) Uani 1 2 d S . . H4A H 0.877(3) -0.285(2) 0.7500 0.042(14) Uiso 1 2 d S . . C5 C 0.83474(16) -0.29076(16) 0.5957(2) 0.0353(8) Uani 1 1 d . . . H5A H 0.8244(13) -0.2680(13) 0.5349(16) 0.010(6) Uiso 1 1 d . . . C6 C 0.90790(19) -0.23432(19) 0.5866(3) 0.0505(11) Uani 1 1 d . . . H6A H 0.926(2) -0.241(2) 0.521(3) 0.067(13) Uiso 1 1 d . . . H6B H 0.944(3) -0.237(3) 0.639(3) 0.093(17) Uiso 1 1 d . . . C7 C 0.9134(2) -0.1649(2) 0.5867(4) 0.0637(13) Uani 1 1 d . . . H7A H 0.973(3) -0.129(3) 0.576(3) 0.083(15) Uiso 1 1 d . . . H7C H 0.900(4) -0.150(4) 0.658(5) 0.17(3) Uiso 1 1 d . . . H7B H 0.873(2) -0.1720(18) 0.539(2) 0.046(10) Uiso 1 1 d . . . C8 C 0.82453(15) -0.36121(16) 0.5855(2) 0.0305(7) Uani 1 1 d . . . C9 C 0.76115(16) -0.41581(17) 0.5713(2) 0.0348(8) Uani 1 1 d . . . C10 C 0.75146(18) -0.47993(18) 0.5631(2) 0.0391(8) Uani 1 1 d . . . H10A H 0.7115(19) -0.515(2) 0.553(2) 0.043(10) Uiso 1 1 d . . . C11 C 0.80548(18) -0.49098(17) 0.5708(2) 0.0387(8) Uani 1 1 d . . . C12 C 0.86952(17) -0.43829(17) 0.5865(2) 0.0332(7) Uani 1 1 d . . . C13 C 0.87717(17) -0.37468(17) 0.5919(2) 0.0320(8) Uani 1 1 d . . . H13A H 0.915(3) -0.351(3) 0.600(3) 0.089(19) Uiso 1 1 d . . . C14 C 0.92745(17) -0.45213(18) 0.5959(2) 0.0363(8) Uani 1 1 d . . . H14A H 0.9247(17) -0.4775(18) 0.552(2) 0.037(10) Uiso 1 1 d . . . C15 C 0.99603(19) -0.3888(2) 0.5876(3) 0.0456(10) Uani 1 1 d . . . H15B H 0.999(2) -0.357(2) 0.634(3) 0.062(13) Uiso 1 1 d . . . H15A H 0.996(2) -0.373(2) 0.532(3) 0.051(11) Uiso 1 1 d . . . C16 C 1.0537(2) -0.4031(3) 0.5935(3) 0.0527(11) Uani 1 1 d . . . H16B H 1.057(2) -0.418(2) 0.645(3) 0.063(14) Uiso 1 1 d . . . H16A H 1.094(2) -0.360(2) 0.593(3) 0.058(13) Uiso 1 1 d . . . H16C H 1.045(2) -0.443(2) 0.550(3) 0.068(13) Uiso 1 1 d . . . C17 C 0.92262(15) -0.48765(15) 0.6760(2) 0.0315(7) Uani 1 1 d . . . C18 C 0.9240(2) -0.4585(2) 0.7500 0.0318(10) Uani 1 2 d S . . H18A H 0.928(2) -0.410(2) 0.7500 0.015(10) Uiso 1 2 d S . . C19 C 0.91898(17) -0.54983(16) 0.6775(2) 0.0364(8) Uani 1 1 d . . . C20 C 0.9172(3) -0.5808(2) 0.7500 0.0414(13) Uani 1 2 d S . . H20A H 0.919(3) -0.618(3) 0.7500 0.049(15) Uiso 1 2 d S . . C21 C 0.74754(18) 0.16723(17) 0.3684(3) 0.0423(9) Uani 1 1 d . . . H21A H 0.794(2) 0.1698(19) 0.369(2) 0.048(11) Uiso 1 1 d . . . C22 C 0.74363(16) 0.22539(16) 0.3622(2) 0.0371(8) Uani 1 1 d . . . H22A H 0.788(2) 0.275(2) 0.352(2) 0.061(12) Uiso 1 1 d . . . C23 C 0.68118(15) 0.22018(14) 0.3615(2) 0.0278(7) Uani 1 1 d . . . C24 C 0.62546(17) 0.15652(16) 0.3659(3) 0.0433(9) Uani 1 1 d . . . H24A H 0.576(2) 0.150(2) 0.361(3) 0.061(12) Uiso 1 1 d . . . C25 C 0.63438(18) 0.10141(17) 0.3712(3) 0.0443(10) Uani 1 1 d . . . H25A H 0.594(3) 0.048(3) 0.371(3) 0.101(18) Uiso 1 1 d . . . C26 C 0.67357(14) 0.28035(14) 0.35884(19) 0.0258(6) Uani 1 1 d . . . C27 C 0.3071(7) -0.4428(6) 0.2500 0.080(3) Uani 0.67 2 d SP . . C28 C 0.4304(9) -0.3184(9) 0.2500 0.099(5) Uani 0.67 2 d SP . . C29 C 0.3080(6) -0.3742(5) 0.2500 0.061(3) Uani 0.67 2 d SP . . C30 C 0.3760(5) -0.3732(6) 0.2500 0.059(2) Uani 0.67 2 d SP . . C31 C 0.8400(7) -0.2522(8) 0.2026(10) 0.075(4) Uani 0.50 1 d P . . C32 C 0.7784(6) -0.3083(7) 0.2052(9) 0.066(3) Uani 0.50 1 d P . . C33 C 0.7420(7) -0.3368(7) 0.2781(8) 0.079(4) Uani 0.50 1 d P . . C34 C 0.7713(5) -0.3072(6) 0.3535(7) 0.068(3) Uani 0.50 1 d P . . C35 C 0.8370(8) -0.2484(7) 0.3565(8) 0.074(3) Uani 0.50 1 d P . . C36 C 0.8702(6) -0.2204(6) 0.2792(7) 0.063(3) Uani 0.50 1 d P . . C37 C 0.8807(7) -0.2225(8) 0.1229(9) 0.103(5) Uani 0.50 1 d P . . C38 C 0.9370(6) -0.1574(6) 0.2838(7) 0.094(4) Uani 0.50 1 d P . . O1 O 0.71212(12) -0.28923(13) 0.60372(15) 0.0406(6) Uani 1 1 d . . . O2 O 0.70473(11) -0.40984(13) 0.56419(16) 0.0398(6) Uani 1 1 d . . . H2 H 0.719(3) -0.362(3) 0.569(3) 0.091(17) Uiso 1 1 d . . . O3 O 0.79414(13) -0.55531(12) 0.56091(18) 0.0488(7) Uani 1 1 d . . . H3 H 0.8281 -0.5564 0.5731 0.073 Uiso 1 1 calc R . . O4 O 0.91718(19) -0.57792(14) 0.60311(18) 0.0681(10) Uani 1 1 d . . . H4 H 0.895(3) -0.633(3) 0.614(4) 0.11(2) Uiso 1 1 d . . . O5 O 0.6667 -0.6667 0.5385(3) 0.0495(12) Uani 1 3 d S . . H1A H 0.670(3) -0.288(3) 0.7500 0.044(14) Uiso 1 2 d S . . H1 H 0.672(3) -0.285(3) 0.613(3) 0.086(16) Uiso 1 1 d . . . H5 H 0.639(10) -0.672(14) 0.592(6) 0.20(6) Uiso 0.67 1 d P . . 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 0.0405(16) 0.0273(14) 0.0489(18) -0.0072(13) -0.0028(14) 0.0210(12) N2 0.0236(12) 0.0237(12) 0.0373(15) -0.0031(11) -0.0034(11) 0.0121(10) C1 0.020(2) 0.036(2) 0.051(3) 0.000 0.000 0.0185(19) C2 0.0226(14) 0.0360(17) 0.044(2) 0.0009(15) -0.0024(14) 0.0168(13) C3 0.0210(14) 0.0276(15) 0.048(2) 0.0020(14) 0.0018(14) 0.0138(12) C4 0.019(2) 0.027(2) 0.054(3) 0.000 0.000 0.0126(18) C5 0.0252(15) 0.0311(16) 0.050(2) 0.0053(15) 0.0080(15) 0.0141(14) C6 0.0347(19) 0.040(2) 0.074(3) 0.011(2) 0.010(2) 0.0166(17) C7 0.051(3) 0.040(2) 0.094(4) 0.013(2) 0.016(3) 0.019(2) C8 0.0235(14) 0.0319(16) 0.0354(18) 0.0044(14) 0.0039(13) 0.0133(13) C9 0.0255(15) 0.0378(18) 0.0395(19) 0.0065(15) 0.0010(14) 0.0146(14) C10 0.0288(17) 0.0351(18) 0.048(2) 0.0029(16) -0.0055(16) 0.0117(15) C11 0.0400(19) 0.0313(17) 0.046(2) -0.0021(15) -0.0052(16) 0.0190(15) C12 0.0321(17) 0.0350(17) 0.0354(18) 0.0030(14) 0.0037(14) 0.0190(14) C13 0.0242(16) 0.0321(17) 0.0383(19) 0.0020(14) 0.0056(14) 0.0131(14) C14 0.0367(18) 0.0427(19) 0.038(2) 0.0020(16) 0.0054(15) 0.0264(16) C15 0.0360(19) 0.054(2) 0.056(3) 0.023(2) 0.0163(18) 0.0297(18) C16 0.040(2) 0.064(3) 0.066(3) 0.019(2) 0.014(2) 0.035(2) C17 0.0270(15) 0.0274(15) 0.0432(19) 0.0009(14) 0.0033(14) 0.0160(13) C18 0.032(2) 0.028(2) 0.042(3) 0.000 0.000 0.020(2) C19 0.0355(17) 0.0280(16) 0.046(2) -0.0038(15) 0.0042(16) 0.0163(14) C20 0.046(3) 0.021(2) 0.060(4) 0.000 0.000 0.019(2) C21 0.0336(18) 0.0324(18) 0.066(3) -0.0023(17) 0.0024(18) 0.0207(15) C22 0.0272(16) 0.0270(16) 0.059(2) -0.0039(16) 0.0002(16) 0.0148(14) C23 0.0268(15) 0.0222(14) 0.0358(17) -0.0034(13) -0.0001(13) 0.0133(12) C24 0.0292(17) 0.0232(16) 0.076(3) -0.0042(17) -0.0060(18) 0.0121(14) C25 0.0363(18) 0.0230(16) 0.072(3) -0.0067(17) -0.0029(18) 0.0138(15) C26 0.0236(14) 0.0237(14) 0.0314(16) -0.0006(13) -0.0004(13) 0.0128(12) C27 0.109(10) 0.088(8) 0.059(7) 0.000 0.000 0.061(8) C28 0.137(13) 0.163(16) 0.058(7) 0.000 0.000 0.122(13) C29 0.083(8) 0.065(6) 0.040(5) 0.000 0.000 0.040(6) C30 0.053(6) 0.069(7) 0.051(6) 0.000 0.000 0.028(5) C31 0.061(9) 0.105(11) 0.086(10) -0.031(9) -0.024(8) 0.062(9) C32 0.052(7) 0.095(10) 0.064(8) -0.006(7) -0.006(6) 0.046(7) C33 0.074(8) 0.099(9) 0.082(11) -0.015(7) -0.010(7) 0.057(8) C34 0.065(7) 0.102(9) 0.052(6) 0.001(6) 0.004(5) 0.053(7) C35 0.102(11) 0.096(9) 0.049(7) -0.005(7) 0.007(7) 0.067(9) C36 0.059(7) 0.078(8) 0.060(8) -0.009(5) 0.003(5) 0.039(6) C37 0.057(7) 0.147(13) 0.104(11) 0.039(9) 0.041(7) 0.051(8) C38 0.069(7) 0.092(8) 0.104(10) -0.018(6) -0.001(6) 0.028(6) O1 0.0276(12) 0.0507(15) 0.0484(15) 0.0038(12) -0.0028(11) 0.0234(11) O2 0.0231(11) 0.0408(14) 0.0558(16) 0.0053(12) -0.0031(11) 0.0161(10) O3 0.0446(15) 0.0304(13) 0.0700(19) -0.0033(12) -0.0092(13) 0.0178(11) O4 0.115(3) 0.0338(15) 0.0532(18) -0.0027(13) 0.0211(17) 0.0352(17) O5 0.0469(17) 0.0469(17) 0.055(3) 0.000 0.000 0.0235(8) _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 C25 1.324(4) . ? N1 C21 1.325(4) . ? N2 C26 1.333(4) 3_665 ? N2 C26 1.342(4) . ? C1 C2 1.381(4) 10_557 ? C1 C2 1.381(4) . ? C2 O1 1.374(4) . ? C2 C3 1.407(4) . ? C3 C4 1.387(4) . ? C3 C5 1.527(5) . ? C4 C3 1.387(4) 10_557 ? C5 C8 1.525(4) . ? C5 C6 1.534(5) . ? C6 C7 1.537(6) . ? C8 C9 1.387(4) . ? C8 C13 1.395(4) . ? C9 O2 1.376(4) . ? C9 C10 1.383(5) . ? C10 C11 1.392(5) . ? C11 O3 1.377(4) . ? C11 C12 1.385(5) . ? C12 C13 1.386(5) . ? C12 C14 1.524(5) . ? C14 C17 1.524(5) . ? C14 C15 1.526(5) . ? C15 C16 1.520(5) . ? C17 C18 1.382(4) . ? C17 C19 1.390(4) . ? C18 C17 1.382(4) 10_557 ? C19 O4 1.374(4) . ? C19 C20 1.380(4) . ? C20 C19 1.380(4) 10_557 ? C21 C22 1.388(5) . ? C22 C23 1.380(4) . ? C23 C24 1.383(4) . ? C23 C26 1.479(4) . ? C24 C25 1.384(5) . ? C26 N2 1.333(4) 2_655 ? C27 C28 1.447(19) 3_655 ? C27 C29 1.567(15) . ? C27 C30 1.592(17) . ? C28 C30 1.255(19) . ? C28 C29 1.299(16) 2_545 ? C28 C27 1.447(19) 2_545 ? C29 C30 1.295(15) 3_655 ? C29 C28 1.299(16) 3_655 ? C29 C29 1.421(17) 2_545 ? C29 C29 1.421(17) 3_655 ? C29 C30 1.553(16) . ? C30 C29 1.295(15) 2_545 ? C31 C36 0.774(13) 10_556 ? C31 C35 0.982(15) 10_556 ? C31 C32 1.359(19) . ? C31 C36 1.447(16) . ? C31 C37 1.56(2) . ? C31 C31 1.56(3) 10_556 ? C31 C34 1.717(17) 10_556 ? C31 C32 2.04(2) 10_556 ? C32 C33 0.810(13) 10_556 ? C32 C34 0.982(14) 10_556 ? C32 C33 1.421(15) . ? C32 C32 1.47(3) 10_556 ? C32 C35 1.70(2) 10_556 ? C32 C31 2.04(2) 10_556 ? C33 C32 0.810(13) 10_556 ? C33 C33 0.93(3) 10_556 ? C33 C34 1.413(17) . ? C34 C32 0.982(14) 10_556 ? C34 C35 1.438(18) . ? C34 C31 1.717(17) 10_556 ? C35 C37 0.938(15) 10_556 ? C35 C31 0.982(15) 10_556 ? C35 C36 1.457(17) . ? C35 C32 1.70(2) 10_556 ? C36 C31 0.774(13) 10_556 ? C36 C36 0.96(2) 10_556 ? C36 C38 1.495(16) . ? C36 C37 1.633(18) 10_556 ? C36 C38 1.817(16) 10_556 ? C37 C35 0.938(15) 10_556 ? C37 C36 1.633(18) 10_556 ? C38 C38 1.11(2) 10_556 ? C38 C36 1.817(16) 10_556 ? 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 C25 N1 C21 117.4(3) . . ? C26 N2 C26 115.3(3) 3_665 . ? C2 C1 C2 120.8(4) 10_557 . ? O1 C2 C1 121.8(3) . . ? O1 C2 C3 117.5(3) . . ? C1 C2 C3 120.6(3) . . ? C4 C3 C2 117.0(3) . . ? C4 C3 C5 121.4(3) . . ? C2 C3 C5 121.4(3) . . ? C3 C4 C3 124.1(4) 10_557 . ? C8 C5 C3 109.9(3) . . ? C8 C5 C6 114.1(3) . . ? C3 C5 C6 112.4(3) . . ? C5 C6 C7 111.4(3) . . ? C9 C8 C13 116.6(3) . . ? C9 C8 C5 120.9(3) . . ? C13 C8 C5 122.5(3) . . ? O2 C9 C10 116.2(3) . . ? O2 C9 C8 122.7(3) . . ? C10 C9 C8 121.1(3) . . ? C9 C10 C11 120.2(3) . . ? O3 C11 C12 120.6(3) . . ? O3 C11 C10 118.6(3) . . ? C12 C11 C10 120.8(3) . . ? C11 C12 C13 116.9(3) . . ? C11 C12 C14 119.6(3) . . ? C13 C12 C14 123.4(3) . . ? C12 C13 C8 124.3(3) . . ? C17 C14 C12 111.2(3) . . ? C17 C14 C15 110.6(3) . . ? C12 C14 C15 112.7(3) . . ? C16 C15 C14 112.6(3) . . ? C18 C17 C19 117.3(3) . . ? C18 C17 C14 121.5(3) . . ? C19 C17 C14 121.1(3) . . ? C17 C18 C17 123.4(4) 10_557 . ? O4 C19 C20 122.7(3) . . ? O4 C19 C17 116.1(3) . . ? C20 C19 C17 121.2(3) . . ? C19 C20 C19 119.6(4) . 10_557 ? N1 C21 C22 123.5(3) . . ? C23 C22 C21 118.9(3) . . ? C22 C23 C24 117.7(3) . . ? C22 C23 C26 121.6(3) . . ? C24 C23 C26 120.7(3) . . ? C23 C24 C25 119.3(3) . . ? N1 C25 C24 123.2(3) . . ? N2 C26 N2 124.7(3) 2_655 . ? N2 C26 C23 117.7(2) 2_655 . ? N2 C26 C23 117.6(3) . . ? C28 C27 C29 50.9(8) 3_655 . ? C28 C27 C30 109.8(10) 3_655 . ? C29 C27 C30 58.9(7) . . ? C30 C28 C29 60.9(10) . 2_545 ? C30 C28 C27 130.2(13) . 2_545 ? C29 C28 C27 69.3(9) 2_545 2_545 ? C30 C29 C28 57.9(10) 3_655 3_655 ? C30 C29 C29 129.6(11) 3_655 2_545 ? C28 C29 C29 172.5(15) 3_655 2_545 ? C30 C29 C29 69.6(11) 3_655 3_655 ? C28 C29 C29 127.5(15) 3_655 3_655 ? C29 C29 C29 60.000(1) 2_545 3_655 ? C30 C29 C30 179.1(9) 3_655 . ? C28 C29 C30 121.2(11) 3_655 . ? C29 C29 C30 51.4(9) 2_545 . ? C29 C29 C30 111.4(9) 3_655 . ? C30 C29 C27 117.7(10) 3_655 . ? C28 C29 C27 59.8(10) 3_655 . ? C29 C29 C27 112.8(13) 2_545 . ? C29 C29 C27 172.8(13) 3_655 . ? C30 C29 C27 61.4(8) . . ? C28 C30 C29 61.3(8) . 2_545 ? C28 C30 C29 120.3(11) . . ? C29 C30 C29 59.1(9) 2_545 . ? C28 C30 C27 180.0(12) . . ? C29 C30 C27 118.8(10) 2_545 . ? C29 C30 C27 59.7(7) . . ? C36 C31 C35 112(3) 10_556 10_556 ? C36 C31 C32 154(3) 10_556 . ? C35 C31 C32 91.7(15) 10_556 . ? C36 C31 C36 37.7(15) 10_556 . ? C35 C31 C36 148.6(19) 10_556 . ? C32 C31 C36 117.5(15) . . ? C36 C31 C37 82(2) 10_556 . ? C35 C31 C37 34.9(13) 10_556 . ? C32 C31 C37 123.7(14) . . ? C36 C31 C37 118.7(10) . . ? C36 C31 C31 67.2(19) 10_556 10_556 ? C35 C31 C31 172.0(10) 10_556 10_556 ? C32 C31 C31 88.2(10) . 10_556 ? C36 C31 C31 29.5(7) . 10_556 ? C37 C31 C31 147.4(8) . 10_556 ? C36 C31 C34 165(2) 10_556 10_556 ? C35 C31 C34 56.9(12) 10_556 10_556 ? C32 C31 C34 34.8(7) . 10_556 ? C36 C31 C34 150.7(13) . 10_556 ? C37 C31 C34 90.0(11) . 10_556 ? C31 C31 C34 122.5(7) 10_556 10_556 ? C36 C31 C32 109(2) 10_556 10_556 ? C35 C31 C32 137.4(16) 10_556 10_556 ? C32 C31 C32 46.4(11) . 10_556 ? C36 C31 C32 71.2(10) . 10_556 ? C37 C31 C32 168.8(12) . 10_556 ? C31 C31 C32 41.9(5) 10_556 10_556 ? C34 C31 C32 80.8(9) 10_556 10_556 ? C33 C32 C34 104(2) 10_556 10_556 ? C33 C32 C31 161(2) 10_556 . ? C34 C32 C31 93.0(15) 10_556 . ? C33 C32 C33 37.8(15) 10_556 . ? C34 C32 C33 140.8(13) 10_556 . ? C31 C32 C33 123.9(14) . . ? C33 C32 C32 70.2(17) 10_556 10_556 ? C34 C32 C32 169.6(9) 10_556 10_556 ? C31 C32 C32 91.8(10) . 10_556 ? C33 C32 C32 32.4(6) . 10_556 ? C33 C32 C35 160(2) 10_556 10_556 ? C34 C32 C35 57.7(11) 10_556 10_556 ? C31 C32 C35 35.3(7) . 10_556 ? C33 C32 C35 157.4(12) . 10_556 ? C32 C32 C35 126.7(7) 10_556 10_556 ? C33 C32 C31 111.8(19) 10_556 10_556 ? C34 C32 C31 142.0(15) 10_556 10_556 ? C31 C32 C31 49.9(11) . 10_556 ? C33 C32 C31 74.1(9) . 10_556 ? C32 C32 C31 41.9(5) 10_556 10_556 ? C35 C32 C31 84.9(9) 10_556 10_556 ? C32 C33 C33 109.8(17) 10_556 10_556 ? C32 C33 C34 42.5(14) 10_556 . ? C33 C33 C34 151.3(8) 10_556 . ? C32 C33 C32 77(2) 10_556 . ? C33 C33 C32 32.4(6) 10_556 . ? C34 C33 C32 119.3(12) . . ? C32 C34 C33 33.9(9) 10_556 . ? C32 C34 C35 87.1(13) 10_556 . ? C33 C34 C35 120.4(12) . . ? C32 C34 C31 52.2(12) 10_556 10_556 ? C33 C34 C31 85.7(11) . 10_556 ? C35 C34 C31 34.8(7) . 10_556 ? C37 C35 C31 108(2) 10_556 10_556 ? C37 C35 C34 153.6(18) 10_556 . ? C31 C35 C34 88.3(15) 10_556 . ? C37 C35 C36 83.0(15) 10_556 . ? C31 C35 C36 29.6(12) 10_556 . ? C34 C35 C36 117.2(12) . . ? C37 C35 C32 153.3(15) 10_556 10_556 ? C31 C35 C32 53.1(12) 10_556 10_556 ? C34 C35 C32 35.2(6) . 10_556 ? C36 C35 C32 82.3(10) . 10_556 ? C31 C36 C36 112.8(19) 10_556 10_556 ? C31 C36 C31 83(2) 10_556 . ? C36 C36 C31 29.5(8) 10_556 . ? C31 C36 C35 38.8(18) 10_556 . ? C36 C36 C35 150.8(8) 10_556 . ? C31 C36 C35 121.5(12) . . ? C31 C36 C38 154(2) 10_556 . ? C36 C36 C38 92.9(6) 10_556 . ? C31 C36 C38 122.3(10) . . ? C35 C36 C38 116.2(10) . . ? C31 C36 C37 70.5(18) 10_556 10_556 ? C36 C36 C37 170.5(6) 10_556 10_556 ? C31 C36 C37 152.1(13) . 10_556 ? C35 C36 C37 34.8(7) . 10_556 ? C38 C36 C37 83.3(9) . 10_556 ? C31 C36 C38 167(2) 10_556 10_556 ? C36 C36 C38 55.3(5) 10_556 10_556 ? C31 C36 C38 84.7(8) . 10_556 ? C35 C36 C38 153.7(11) . 10_556 ? C38 C36 C38 37.6(9) . 10_556 ? C37 C36 C38 120.5(10) 10_556 10_556 ? C35 C37 C31 36.8(10) 10_556 . ? C35 C37 C36 62.3(12) 10_556 10_556 ? C31 C37 C36 27.9(5) . 10_556 ? C38 C38 C36 87.1(6) 10_556 . ? C38 C38 C36 55.3(5) 10_556 10_556 ? C36 C38 C36 31.8(8) . 10_556 ? 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 O1 H1 N1 0.97(6) 1.77(6) 2.712(3) 162(5) 9_546 O2 H2 O1 0.98(6) 1.85(6) 2.769(4) 155(5) . O3 H3 O4 0.82 2.39 3.197(5) 171.0 . O4 H4 O2 1.11(6) 1.75(6) 2.705(4) 140(5) 3_755 O5 H5 O3 1.06(12) 2.27(13) 2.789(3) 108(8) 2_535 _diffrn_measured_fraction_theta_max 0.951 _diffrn_reflns_theta_full 31.09 _diffrn_measured_fraction_theta_full 0.951 _refine_diff_density_max 0.797 _refine_diff_density_min -0.663 _refine_diff_density_rms 0.166 data_p63m_c _database_code_depnum_ccdc_archive 'CCDC 230026' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C168 H196 N12 O26' _chemical_formula_weight 2799.37 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 hexagonal _symmetry_space_group_name_H-M P6(3)/m loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z' '-x+y, -x, z' '-x, -y, z+1/2' 'y, -x+y, z+1/2' 'x-y, x, z+1/2' '-x, -y, -z' 'y, -x+y, -z' 'x-y, x, -z' 'x, y, -z-1/2' '-y, x-y, -z-1/2' '-x+y, -x, -z-1/2' _cell_length_a 23.0604(11) _cell_length_b 23.0604(11) _cell_length_c 16.2247(13) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 7472.1(8) _cell_formula_units_Z 2 _cell_measurement_temperature 90(1) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prismatic _exptl_crystal_colour yellow _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.244 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2992 _exptl_absorpt_coefficient_mu 0.084 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 90(1) _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 'SMART CCD 1000' _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 86480 _diffrn_reflns_av_R_equivalents 0.1088 _diffrn_reflns_av_sigmaI/netI 0.0379 _diffrn_reflns_limit_h_min -29 _diffrn_reflns_limit_h_max 29 _diffrn_reflns_limit_k_min -29 _diffrn_reflns_limit_k_max 29 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 1.77 _diffrn_reflns_theta_max 27.00 _reflns_number_total 5634 _reflns_number_gt 3830 _reflns_threshold_expression >2sigma(I) _computing_data_collection SMART _computing_cell_refinement SMART _computing_data_reduction SAINT _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics XP _computing_publication_material XCIF _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^)+(0.0870P)^2^+4.7409P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0031(4) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 5634 _refine_ls_number_parameters 461 _refine_ls_number_restraints 8 _refine_ls_R_factor_all 0.0876 _refine_ls_R_factor_gt 0.0547 _refine_ls_wR_factor_ref 0.1714 _refine_ls_wR_factor_gt 0.1400 _refine_ls_goodness_of_fit_ref 1.029 _refine_ls_restrained_S_all 1.036 _refine_ls_shift/su_max 0.002 _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 0.28953(8) -0.00112(7) 0.60191(9) 0.0284(4) Uani 1 1 d . . . O2 O 0.41145(8) 0.11362(7) 0.56887(10) 0.0295(4) Uani 1 1 d . . . O3 O 0.55384(8) 0.34748(8) 0.56642(12) 0.0381(4) Uani 1 1 d D . . O4 O 0.5785(4) 0.4827(10) 0.6000(3) 0.033(3) Uani 0.68(6) 1 d P . . O4' O 0.5720(7) 0.5039(15) 0.6046(10) 0.029(4) Uani 0.32(6) 1 d P . . O5 O 0.6667 0.3333 0.5401(3) 0.0627(10) Uani 1 3 d SD . . C1 C 0.28471(14) -0.00498(14) 0.7500 0.0244(6) Uani 1 2 d S . . C2 C 0.28570(10) 0.02534(9) 0.67613(13) 0.0234(4) Uani 1 1 d . . . C3 C 0.28632(9) 0.08652(9) 0.67473(13) 0.0213(4) Uani 1 1 d . . . C4 C 0.28680(13) 0.11523(13) 0.7500 0.0216(6) Uani 1 2 d S . . C5 C 0.29065(10) 0.12149(10) 0.59315(13) 0.0237(4) Uani 1 1 d . . . C6 C 0.23276(10) 0.13525(10) 0.58246(15) 0.0286(5) Uani 1 1 d . . . C7 C 0.16510(12) 0.07045(12) 0.5809(2) 0.0400(6) Uani 1 1 d . . . C8 C 0.36030(10) 0.18325(9) 0.58463(12) 0.0213(4) Uani 1 1 d . . . C9 C 0.41611(10) 0.17544(10) 0.57446(13) 0.0239(4) Uani 1 1 d . . . C10 C 0.48022(10) 0.23031(11) 0.56860(14) 0.0280(5) Uani 1 1 d . . . C11 C 0.48982(10) 0.29451(10) 0.57428(14) 0.0265(5) Uani 1 1 d . . . C12 C 0.43568(10) 0.30509(10) 0.58563(12) 0.0216(4) Uani 1 1 d . . . C13 C 0.37211(10) 0.24848(10) 0.58985(12) 0.0207(4) Uani 1 1 d . . . C14 C 0.44808(10) 0.37604(10) 0.59473(13) 0.0222(4) Uani 1 1 d . . . C15 C 0.38404(11) 0.38057(10) 0.58892(14) 0.0264(5) Uani 1 1 d . . . C16 C 0.39797(13) 0.45237(11) 0.59592(16) 0.0332(5) Uani 1 1 d . . . C17 C 0.45560(14) 0.37973(13) 0.7500 0.0220(6) Uani 1 2 d S . . C18 C 0.48490(9) 0.40706(9) 0.67505(12) 0.0215(4) Uani 1 1 d . . . C19 C 0.54826(10) 0.46408(11) 0.67637(13) 0.0294(5) Uani 1 1 d . . . C20 C 0.57977(15) 0.49261(16) 0.7500 0.0330(7) Uani 1 2 d S . . C21 C 0.36875(12) -0.10087(11) 0.63060(17) 0.0352(5) Uani 1 1 d . . . C22 C 0.37683(11) -0.15620(10) 0.63695(17) 0.0344(6) Uani 1 1 d . . . C23 C 0.32066(10) -0.21944(9) 0.63690(14) 0.0253(4) Uani 1 1 d . . . C24 C 0.25823(10) -0.22466(10) 0.63069(14) 0.0266(5) Uani 1 1 d . . . C25 C 0.25490(11) -0.16657(11) 0.62343(14) 0.0289(5) Uani 1 1 d . . . C26 C 0.32734(10) -0.28009(9) 0.63976(14) 0.0263(5) Uani 1 1 d . . . C29 C 0.1141(3) 0.1864(3) 0.7500 0.0755(16) Uani 1 2 d S . . C30 C 0.13276(17) 0.22920(19) 0.6721(2) 0.0626(9) Uani 1 1 d . . . C31 C 0.20626(16) 0.28293(16) 0.6730(2) 0.0585(9) Uani 1 1 d . . . C32 C 0.2248(2) 0.3256(2) 0.7500 0.0557(11) Uani 1 2 d S . . N1 N 0.30882(9) -0.10560(8) 0.62361(12) 0.0289(4) Uani 1 1 d . . . N2 N 0.27102(8) -0.33949(8) 0.64023(12) 0.0277(4) Uani 1 1 d . . . H6B H 0.2348(12) 0.1652(12) 0.6252(16) 0.034(6) Uiso 1 1 d . . . H5A H 0.2832(11) 0.0914(11) 0.5430(14) 0.024(6) Uiso 1 1 d . . . H16B H 0.4150(12) 0.4699(12) 0.6531(16) 0.035(7) Uiso 1 1 d . . . H13A H 0.3356(12) 0.2556(11) 0.5970(14) 0.024(6) Uiso 1 1 d . . . H15B H 0.3609(12) 0.3613(11) 0.5359(15) 0.031(6) Uiso 1 1 d . . . H15A H 0.3516(13) 0.3529(13) 0.6317(16) 0.038(7) Uiso 1 1 d . . . H4A H 0.2906(15) 0.1587(16) 0.7500 0.021(8) Uiso 1 2 d S . . H17A H 0.4093(14) 0.3404(14) 0.7500 0.012(7) Uiso 1 2 d S . . H7C H 0.1553(14) 0.0446(15) 0.6345(19) 0.054(8) Uiso 1 1 d . . . H6A H 0.2406(12) 0.1611(12) 0.5284(15) 0.033(6) Uiso 1 1 d . . . H7B H 0.1275(14) 0.0813(13) 0.5738(16) 0.044(7) Uiso 1 1 d . . . H7A H 0.1683(13) 0.0431(14) 0.5372(18) 0.044(7) Uiso 1 1 d . . . H25A H 0.2107(13) -0.1692(12) 0.6181(15) 0.032(6) Uiso 1 1 d . . . H16A H 0.4313(13) 0.4810(13) 0.5514(16) 0.039(7) Uiso 1 1 d . . . H1A H 0.2852(16) -0.0485(16) 0.7500 0.026(8) Uiso 1 2 d S . . H21A H 0.4063(14) -0.0560(14) 0.6315(16) 0.044(7) Uiso 1 1 d . . . H14A H 0.4747(12) 0.4028(12) 0.5479(15) 0.031(6) Uiso 1 1 d . . . H10A H 0.5206(12) 0.2244(12) 0.5615(14) 0.032(6) Uiso 1 1 d . . . H22A H 0.4198(15) -0.1521(14) 0.6392(17) 0.050(8) Uiso 1 1 d . . . H24A H 0.2181(13) -0.2685(13) 0.6325(15) 0.036(7) Uiso 1 1 d . . . H16C H 0.3573(14) 0.4539(13) 0.5887(16) 0.039(7) Uiso 1 1 d . . . H30B H 0.1201(18) 0.1984(19) 0.623(2) 0.082(11) Uiso 1 1 d . . . H2 H 0.370(2) 0.082(2) 0.572(2) 0.092(6) Uiso 1 1 d . . . H1 H 0.295(2) -0.037(2) 0.612(2) 0.092(6) Uiso 1 1 d . . . H29B H 0.069(3) 0.158(3) 0.7500 0.080(16) Uiso 1 2 d S . . H32A H 0.2335(16) 0.2582(16) 0.675(2) 0.068(10) Uiso 1 1 d . . . H4 H 0.621(2) 0.523(2) 0.603(2) 0.092(6) Uiso 1 1 d . . . H31A H 0.2158(19) 0.3125(19) 0.619(3) 0.086(12) Uiso 1 1 d . . . H20A H 0.626(2) 0.530(2) 0.7500 0.056(12) Uiso 1 2 d S . . H30A H 0.1046(18) 0.2518(18) 0.666(2) 0.079(11) Uiso 1 1 d . . . H29A H 0.140(3) 0.160(3) 0.7500 0.081(16) Uiso 1 2 d S . . H32B H 0.197(2) 0.344(2) 0.7500 0.067(13) Uiso 1 2 d S . . H32A' H 0.281(4) 0.363(4) 0.7500 0.14(3) Uiso 1 2 d S . . C28 C 0.6547(8) 0.2620(7) 0.7500 0.173(5) Uani 1 2 d SU . . C27 C 0.6006(10) 0.2725(9) 0.7500 0.309(10) Uani 1 2 d SU . . H3 H 0.564(2) 0.385(2) 0.576(3) 0.092(6) Uiso 1 1 d . . . H5 H 0.632(2) 0.337(3) 0.571(2) 0.092(6) Uiso 0.67 1 d PD . . 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 0.0405(9) 0.0216(7) 0.0302(8) -0.0034(6) -0.0015(7) 0.0208(7) O2 0.0284(8) 0.0223(7) 0.0446(9) -0.0034(7) -0.0015(7) 0.0179(6) O3 0.0203(7) 0.0289(8) 0.0593(11) -0.0003(8) 0.0033(7) 0.0080(7) O4 0.0243(16) 0.028(5) 0.0303(15) 0.0063(17) 0.0034(11) 0.001(2) O4' 0.024(3) 0.015(6) 0.040(4) 0.012(3) 0.003(2) 0.004(3) O5 0.0465(12) 0.0465(12) 0.095(3) 0.000 0.000 0.0232(6) C1 0.0270(15) 0.0157(13) 0.0343(16) 0.000 0.000 0.0135(11) C2 0.0240(10) 0.0168(9) 0.0317(11) -0.0036(8) -0.0014(8) 0.0120(8) C3 0.0190(9) 0.0165(9) 0.0306(11) 0.0006(8) -0.0012(8) 0.0104(7) C4 0.0192(13) 0.0119(12) 0.0347(16) 0.000 0.000 0.0086(10) C5 0.0229(10) 0.0188(9) 0.0312(11) -0.0012(8) -0.0037(8) 0.0117(8) C6 0.0236(10) 0.0217(10) 0.0402(13) 0.0004(10) -0.0055(9) 0.0111(9) C7 0.0252(11) 0.0298(12) 0.0605(17) 0.0022(12) -0.0094(11) 0.0104(10) C8 0.0222(9) 0.0195(9) 0.0236(10) 0.0005(8) -0.0019(8) 0.0116(8) C9 0.0278(10) 0.0218(9) 0.0276(11) -0.0019(8) -0.0023(8) 0.0165(8) C10 0.0221(10) 0.0283(11) 0.0372(12) -0.0018(9) 0.0010(9) 0.0152(9) C11 0.0200(9) 0.0236(10) 0.0338(12) -0.0010(9) 0.0020(8) 0.0092(8) C12 0.0242(10) 0.0220(9) 0.0203(10) 0.0009(8) -0.0002(8) 0.0128(8) C13 0.0216(9) 0.0218(9) 0.0218(10) -0.0002(8) -0.0014(8) 0.0131(8) C14 0.0248(10) 0.0179(9) 0.0232(10) 0.0034(8) 0.0011(8) 0.0100(8) C15 0.0297(11) 0.0207(10) 0.0317(12) -0.0019(9) -0.0080(9) 0.0148(9) C16 0.0400(13) 0.0241(11) 0.0409(14) -0.0018(10) -0.0085(11) 0.0201(10) C17 0.0206(13) 0.0149(12) 0.0288(15) 0.000 0.000 0.0076(11) C18 0.0208(9) 0.0168(9) 0.0268(10) 0.0003(8) -0.0011(8) 0.0094(8) C19 0.0214(10) 0.0295(11) 0.0304(12) 0.0056(9) 0.0037(9) 0.0074(9) C20 0.0177(14) 0.0281(16) 0.0375(18) 0.000 0.000 -0.0002(12) C21 0.0324(12) 0.0191(10) 0.0540(15) -0.0027(10) 0.0013(11) 0.0126(9) C22 0.0219(10) 0.0210(10) 0.0604(16) -0.0046(10) -0.0004(10) 0.0107(9) C23 0.0228(10) 0.0195(9) 0.0352(11) -0.0012(8) 0.0017(9) 0.0117(8) C24 0.0231(10) 0.0211(10) 0.0370(12) -0.0014(9) 0.0030(9) 0.0121(9) C25 0.0304(11) 0.0282(11) 0.0349(12) -0.0011(9) 0.0030(9) 0.0198(9) C26 0.0196(9) 0.0182(9) 0.0412(12) -0.0009(9) 0.0006(9) 0.0096(8) C29 0.042(3) 0.058(3) 0.111(5) 0.000 0.000 0.015(2) C30 0.0568(19) 0.072(2) 0.065(2) -0.0132(18) -0.0030(16) 0.0371(18) C31 0.0538(18) 0.0484(16) 0.085(2) -0.0064(16) 0.0124(17) 0.0341(15) C32 0.062(3) 0.043(2) 0.079(3) 0.000 0.000 0.038(2) N1 0.0359(10) 0.0217(8) 0.0344(10) -0.0040(7) 0.0012(8) 0.0183(8) N2 0.0184(8) 0.0171(8) 0.0470(11) 0.0002(8) 0.0028(8) 0.0084(7) C28 0.238(14) 0.223(12) 0.145(9) 0.000 0.000 0.180(12) C27 0.31(2) 0.227(14) 0.48(3) 0.000 0.000 0.199(15) _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 C2 1.373(2) . ? O2 C9 1.378(2) . ? O3 C11 1.373(2) . ? O4 O4' 0.585(17) . ? O4 C19 1.382(5) . ? O4' C19 1.414(10) . ? C1 C2 1.382(2) 10_557 ? C1 C2 1.382(2) . ? C2 C3 1.404(3) . ? C3 C4 1.387(2) . ? C3 C5 1.527(3) . ? C4 C3 1.387(2) 10_557 ? C5 C6 1.528(3) . ? C5 C8 1.530(3) . ? C6 C7 1.529(3) . ? C8 C13 1.391(3) . ? C8 C9 1.396(3) . ? C9 C10 1.388(3) . ? C10 C11 1.386(3) . ? C11 C12 1.399(3) . ? C12 C13 1.394(3) . ? C12 C14 1.521(3) . ? C14 C18 1.524(3) . ? C14 C15 1.534(3) . ? C15 C16 1.525(3) . ? C17 C18 1.381(2) 10_557 ? C17 C18 1.381(2) . ? C18 C19 1.394(3) . ? C19 C20 1.382(3) . ? C20 C19 1.382(3) 10_557 ? C21 N1 1.336(3) . ? C21 C22 1.382(3) . ? C22 C23 1.384(3) . ? C23 C24 1.387(3) . ? C23 C26 1.482(3) . ? C24 C25 1.384(3) . ? C25 N1 1.332(3) . ? C26 N2 1.336(2) . ? C26 N2 1.341(2) 3_655 ? C29 C30 1.526(5) 10_557 ? C29 C30 1.526(5) . ? C30 C31 1.519(5) . ? C31 C32 1.513(4) . ? C32 C31 1.513(4) 10_557 ? N2 C26 1.341(2) 2_545 ? C28 C27 1.383(17) . ? C28 C27 1.608(17) 2_655 ? C27 C28 1.608(17) 3_665 ? 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 O4' O4 C19 81.1(13) . . ? O4 O4' C19 74.8(14) . . ? C2 C1 C2 120.3(2) 10_557 . ? O1 C2 C1 121.63(17) . . ? O1 C2 C3 117.51(18) . . ? C1 C2 C3 120.78(19) . . ? C4 C3 C2 117.34(19) . . ? C4 C3 C5 121.90(17) . . ? C2 C3 C5 120.66(18) . . ? C3 C4 C3 123.5(2) . 10_557 ? C3 C5 C6 112.00(17) . . ? C3 C5 C8 109.33(16) . . ? C6 C5 C8 114.58(16) . . ? C5 C6 C7 111.69(18) . . ? C13 C8 C9 116.89(18) . . ? C13 C8 C5 123.24(17) . . ? C9 C8 C5 119.82(17) . . ? O2 C9 C10 115.80(17) . . ? O2 C9 C8 122.78(18) . . ? C10 C9 C8 121.42(18) . . ? C11 C10 C9 119.85(18) . . ? O3 C11 C10 118.08(18) . . ? O3 C11 C12 120.90(18) . . ? C10 C11 C12 121.01(18) . . ? C13 C12 C11 117.09(18) . . ? C13 C12 C14 123.14(17) . . ? C11 C12 C14 119.76(17) . . ? C8 C13 C12 123.73(18) . . ? C12 C14 C18 110.42(16) . . ? C12 C14 C15 113.42(16) . . ? C18 C14 C15 110.48(17) . . ? C16 C15 C14 112.45(18) . . ? C18 C17 C18 123.4(3) 10_557 . ? C17 C18 C19 117.38(19) . . ? C17 C18 C14 120.53(18) . . ? C19 C18 C14 122.08(18) . . ? O4 C19 C20 124.3(3) . . ? O4 C19 C18 114.1(4) . . ? C20 C19 C18 121.1(2) . . ? O4 C19 O4' 24.1(7) . . ? C20 C19 O4' 117.5(9) . . ? C18 C19 O4' 118.9(5) . . ? C19 C20 C19 119.6(3) . 10_557 ? N1 C21 C22 122.8(2) . . ? C21 C22 C23 119.1(2) . . ? C22 C23 C24 118.38(18) . . ? C22 C23 C26 120.68(18) . . ? C24 C23 C26 120.89(17) . . ? C25 C24 C23 118.65(19) . . ? N1 C25 C24 123.2(2) . . ? N2 C26 N2 125.12(18) . 3_655 ? N2 C26 C23 117.46(17) . . ? N2 C26 C23 117.40(17) 3_655 . ? C30 C29 C30 111.7(4) 10_557 . ? C31 C30 C29 111.0(3) . . ? C32 C31 C30 112.0(3) . . ? C31 C32 C31 111.3(4) . 10_557 ? C25 N1 C21 117.91(17) . . ? C26 N2 C26 114.87(18) . 2_545 ? C27 C28 C27 116.1(17) . 2_655 ? C28 C27 C28 123.9(17) . 3_665 ? 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 O1 H1 N1 0.90(4) 1.78(4) 2.683(2) 175(4) . O2 H2 O1 0.86(4) 1.95(4) 2.785(2) 162(4) . O3 H3 O4 0.80(4) 2.13(5) 2.93(3) 172(4) . O4' H4 O2 0.99(5) 1.81(4) 2.700(11) 149(4) 3_665 O5 H5 O3 0.983(18) 1.935(18) 2.8122(17) 147(3) . _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.900 _refine_diff_density_min -0.510 _refine_diff_density_rms 0.071