# Supplementary Material (ESI) for CrystEngComm # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Chuan-Feng Chen' _publ_contact_author_email CCHEN@ICCAS.AC.CN _publ_section_title ; Synthesis and analysis of hydroxyl substituted triptycene adducts: the competitive recognition between the hydroxyl substituted triptycenes with 4, 4'-bipyridine and solvent molecules ; loop_ _publ_author_name 'Chuan-Feng Chen.' 'Chun Zhang.' # Attachment '1a.cif' data_shelxl _database_code_depnum_ccdc_archive 'CCDC 760760' #TrackingRef '1a.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C43 H34 O5' _chemical_formula_sum 'C43 H34 O5' _chemical_formula_weight 630.70 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 'P 1 21/c 1' 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 10.2936(6) _cell_length_b 13.0927(8) _cell_length_c 24.4245(15) _cell_angle_alpha 90.00 _cell_angle_beta 96.836(3) _cell_angle_gamma 90.00 _cell_volume 3268.3(3) _cell_formula_units_Z 4 _cell_measurement_temperature 113(2) _cell_measurement_reflns_used 3879 _cell_measurement_theta_min 2.5 _cell_measurement_theta_max 25.0 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.282 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1328 _exptl_absorpt_coefficient_mu 0.083 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9852 _exptl_absorpt_correction_T_max 0.9917 _exptl_absorpt_process_details 'Jacobson, R. (1998) Private communication' _exptl_special_details ; ? ; _diffrn_ambient_temperature 113(2) _diffrn_radiation_wavelength 0.71070 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating anode' _diffrn_radiation_monochromator confocal _diffrn_measurement_device_type 'Rigaku Saturn' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 7.31 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 24247 _diffrn_reflns_av_R_equivalents 0.0729 _diffrn_reflns_av_sigmaI/netI 0.0573 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_theta_min 1.68 _diffrn_reflns_theta_max 25.00 _reflns_number_total 5752 _reflns_number_gt 4582 _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 ? _computing_publication_material 'CrystalStructure 3.7.0' _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^)+(0.0699P)^2^+1.5572P] 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 none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5752 _refine_ls_number_parameters 448 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1008 _refine_ls_R_factor_gt 0.0777 _refine_ls_wR_factor_ref 0.1806 _refine_ls_wR_factor_gt 0.1686 _refine_ls_goodness_of_fit_ref 1.172 _refine_ls_restrained_S_all 1.172 _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 O1 O 0.0847(2) 0.94562(16) 0.14182(9) 0.0294(5) Uani 1 1 d . . . H1 H 0.129(3) 1.006(3) 0.1441(14) 0.044 Uiso 1 1 d . . . O2 O 0.1790(2) 0.42961(17) 0.37621(8) 0.0304(5) Uani 1 1 d . . . H2 H 0.096(4) 0.431(3) 0.3706(14) 0.046 Uiso 1 1 d . . . O3 O 0.2379(2) 1.10834(19) 0.32811(10) 0.0439(6) Uani 1 1 d . . . H3 H 0.263(4) 1.157(3) 0.3586(17) 0.066 Uiso 1 1 d . . . O4 O 0.6841(2) 0.74246(18) 0.59596(9) 0.0364(6) Uani 1 1 d . . . H4 H 0.740(4) 0.679(3) 0.6006(15) 0.055 Uiso 1 1 d . . . O5 O 0.2380(2) 0.10909(19) 0.16994(12) 0.0533(7) Uani 1 1 d . . . C1 C 0.1356(3) 0.5760(2) 0.18539(11) 0.0234(7) Uani 1 1 d . . . H1A H 0.0383 0.5712 0.1840 0.028 Uiso 1 1 calc R . . C2 C 0.1839(3) 0.6837(2) 0.17487(11) 0.0224(6) Uani 1 1 d . . . C3 C 0.1059(3) 0.7697(2) 0.16439(11) 0.0244(7) Uani 1 1 d . . . H3A H 0.0139 0.7657 0.1648 0.029 Uiso 1 1 calc R . . C4 C 0.1648(3) 0.8617(2) 0.15328(12) 0.0247(7) Uani 1 1 d . . . C5 C 0.2988(3) 0.8680(2) 0.15259(12) 0.0260(7) Uani 1 1 d . . . H5 H 0.3375 0.9309 0.1438 0.031 Uiso 1 1 calc R . . C6 C 0.3770(3) 0.7822(2) 0.16474(11) 0.0247(7) Uani 1 1 d . . . H6 H 0.4692 0.7871 0.1654 0.030 Uiso 1 1 calc R . . C7 C 0.3199(3) 0.6896(2) 0.17592(11) 0.0216(6) Uani 1 1 d . . . C8 C 0.3890(3) 0.5883(2) 0.18904(12) 0.0236(7) Uani 1 1 d . . . H8 H 0.4863 0.5934 0.1906 0.028 Uiso 1 1 calc R . . C9 C 0.3443(3) 0.5505(2) 0.24308(11) 0.0227(7) Uani 1 1 d . . . C10 C 0.4227(3) 0.5203(2) 0.29039(12) 0.0249(7) Uani 1 1 d . . . H10 H 0.5151 0.5266 0.2926 0.030 Uiso 1 1 calc R . . C11 C 0.3657(3) 0.4806(2) 0.33477(12) 0.0259(7) Uani 1 1 d . . . H11 H 0.4191 0.4599 0.3673 0.031 Uiso 1 1 calc R . . C12 C 0.2312(3) 0.4714(2) 0.33129(11) 0.0234(7) Uani 1 1 d . . . C13 C 0.1500(3) 0.5026(2) 0.28425(11) 0.0236(7) Uani 1 1 d . . . H13 H 0.0576 0.4965 0.2822 0.028 Uiso 1 1 calc R . . C14 C 0.2084(3) 0.5426(2) 0.24061(11) 0.0225(6) Uani 1 1 d . . . C15 C 0.1921(3) 0.5065(2) 0.14351(12) 0.0248(7) Uani 1 1 d . . . C16 C 0.1222(3) 0.4376(2) 0.10848(12) 0.0301(7) Uani 1 1 d . . . H16 H 0.0297 0.4337 0.1068 0.036 Uiso 1 1 calc R . . C17 C 0.1890(3) 0.3741(3) 0.07572(14) 0.0379(8) Uani 1 1 d . . . H17 H 0.1417 0.3266 0.0516 0.046 Uiso 1 1 calc R . . C18 C 0.3242(3) 0.3797(2) 0.07791(13) 0.0361(8) Uani 1 1 d . . . H18 H 0.3690 0.3361 0.0554 0.043 Uiso 1 1 calc R . . C19 C 0.3943(3) 0.4493(2) 0.11322(12) 0.0297(7) Uani 1 1 d . . . H19 H 0.4869 0.4533 0.1147 0.036 Uiso 1 1 calc R . . C20 C 0.3288(3) 0.5124(2) 0.14594(11) 0.0230(7) Uani 1 1 d . . . C21 C 0.2728(3) 0.8651(2) 0.48830(12) 0.0265(7) Uani 1 1 d . . . H21 H 0.2738 0.9245 0.5141 0.032 Uiso 1 1 calc R . . C22 C 0.2635(3) 0.8967(2) 0.42774(12) 0.0261(7) Uani 1 1 d . . . C23 C 0.2543(3) 0.9958(2) 0.40779(12) 0.0286(7) Uani 1 1 d . . . H23 H 0.2541 1.0520 0.4324 0.034 Uiso 1 1 calc R . . C24 C 0.2455(3) 1.0117(3) 0.35089(13) 0.0319(8) Uani 1 1 d . . . C25 C 0.2444(3) 0.9298(3) 0.31456(13) 0.0359(8) Uani 1 1 d . . . H25 H 0.2380 0.9416 0.2759 0.043 Uiso 1 1 calc R . . C26 C 0.2529(3) 0.8306(3) 0.33512(13) 0.0362(8) Uani 1 1 d . . . H26 H 0.2523 0.7745 0.3104 0.043 Uiso 1 1 calc R . . C27 C 0.2623(3) 0.8133(2) 0.39124(13) 0.0305(7) Uani 1 1 d . . . C28 C 0.2703(3) 0.7109(2) 0.42106(13) 0.0319(7) Uani 1 1 d . . . H28 H 0.2695 0.6516 0.3953 0.038 Uiso 1 1 calc R . . C29 C 0.3921(3) 0.7131(2) 0.46355(12) 0.0275(7) Uani 1 1 d . . . C30 C 0.4910(3) 0.6412(2) 0.47076(14) 0.0349(8) Uani 1 1 d . . . H30 H 0.4915 0.5856 0.4458 0.042 Uiso 1 1 calc R . . C31 C 0.5903(3) 0.6502(2) 0.51472(14) 0.0336(8) Uani 1 1 d . . . H31 H 0.6580 0.6006 0.5200 0.040 Uiso 1 1 calc R . . C32 C 0.5893(3) 0.7320(2) 0.55067(12) 0.0292(7) Uani 1 1 d . . . C33 C 0.4916(3) 0.8063(2) 0.54328(12) 0.0270(7) Uani 1 1 d . . . H33 H 0.4926 0.8627 0.5678 0.032 Uiso 1 1 calc R . . C34 C 0.3932(3) 0.7966(2) 0.49979(12) 0.0258(7) Uani 1 1 d . . . C35 C 0.1581(3) 0.7920(2) 0.49257(12) 0.0284(7) Uani 1 1 d . . . C36 C 0.0667(3) 0.7993(3) 0.52924(13) 0.0313(7) Uani 1 1 d . . . H36 H 0.0681 0.8554 0.5539 0.038 Uiso 1 1 calc R . . C37 C -0.0285(3) 0.7228(3) 0.52971(14) 0.0377(8) Uani 1 1 d . . . H37 H -0.0920 0.7272 0.5548 0.045 Uiso 1 1 calc R . . C38 C -0.0307(3) 0.6409(3) 0.49387(15) 0.0413(9) Uani 1 1 d . . . H38 H -0.0956 0.5895 0.4945 0.050 Uiso 1 1 calc R . . C39 C 0.0619(3) 0.6335(3) 0.45689(15) 0.0386(9) Uani 1 1 d . . . H39 H 0.0604 0.5771 0.4323 0.046 Uiso 1 1 calc R . . C40 C 0.1563(3) 0.7086(2) 0.45605(13) 0.0313(7) Uani 1 1 d . . . C41 C 0.3264(4) 0.2554(3) 0.21711(15) 0.0452(9) Uani 1 1 d . . . H41A H 0.4100 0.2237 0.2114 0.068 Uiso 1 1 calc R . . H41B H 0.3227 0.2652 0.2567 0.068 Uiso 1 1 calc R . . H41C H 0.3187 0.3218 0.1984 0.068 Uiso 1 1 calc R . . C42 C 0.2175(3) 0.1885(3) 0.19420(14) 0.0373(8) Uani 1 1 d . . . C43 C 0.0816(3) 0.2207(3) 0.20130(16) 0.0456(9) Uani 1 1 d . . . H43A H 0.0191 0.1803 0.1768 0.068 Uiso 1 1 calc R . . H43B H 0.0705 0.2933 0.1922 0.068 Uiso 1 1 calc R . . H43C H 0.0659 0.2096 0.2396 0.068 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 0.0244(11) 0.0201(12) 0.0431(13) -0.0004(10) 0.0020(10) 0.0022(9) O2 0.0257(11) 0.0376(14) 0.0288(12) 0.0071(10) 0.0065(10) 0.0024(11) O3 0.0496(15) 0.0422(16) 0.0383(14) 0.0108(11) -0.0018(12) -0.0046(12) O4 0.0325(13) 0.0379(14) 0.0374(13) 0.0067(11) -0.0016(10) 0.0048(11) O5 0.0382(14) 0.0329(15) 0.088(2) -0.0137(14) 0.0026(14) -0.0004(12) C1 0.0176(14) 0.0242(17) 0.0282(16) 0.0001(13) 0.0014(12) -0.0024(13) C2 0.0239(15) 0.0254(17) 0.0183(14) -0.0006(12) 0.0031(12) 0.0011(13) C3 0.0210(15) 0.0298(18) 0.0218(15) -0.0017(13) -0.0001(12) 0.0003(13) C4 0.0257(16) 0.0219(17) 0.0257(15) -0.0028(13) -0.0003(12) 0.0008(13) C5 0.0272(16) 0.0212(17) 0.0296(16) -0.0011(13) 0.0032(13) -0.0027(13) C6 0.0189(14) 0.0294(18) 0.0262(15) 0.0009(13) 0.0041(12) -0.0017(13) C7 0.0200(15) 0.0234(16) 0.0216(14) -0.0022(12) 0.0032(12) -0.0014(13) C8 0.0175(14) 0.0247(17) 0.0285(16) 0.0019(13) 0.0024(12) -0.0011(13) C9 0.0229(15) 0.0197(16) 0.0255(15) -0.0015(12) 0.0024(12) -0.0023(13) C10 0.0209(15) 0.0246(17) 0.0288(16) -0.0032(13) 0.0011(12) -0.0006(13) C11 0.0252(16) 0.0269(18) 0.0247(15) 0.0004(13) -0.0003(13) 0.0037(13) C12 0.0258(16) 0.0194(16) 0.0257(15) -0.0005(12) 0.0066(13) 0.0015(13) C13 0.0213(15) 0.0219(17) 0.0274(16) -0.0041(12) 0.0022(12) 0.0003(12) C14 0.0242(15) 0.0179(16) 0.0254(15) -0.0007(12) 0.0032(12) 0.0015(13) C15 0.0239(16) 0.0227(17) 0.0270(16) 0.0035(13) 0.0002(12) 0.0008(13) C16 0.0278(17) 0.0303(19) 0.0307(17) -0.0008(14) -0.0027(13) -0.0012(14) C17 0.043(2) 0.033(2) 0.0353(18) -0.0074(15) -0.0046(16) -0.0012(16) C18 0.046(2) 0.030(2) 0.0322(18) -0.0058(14) 0.0055(16) 0.0068(16) C19 0.0276(16) 0.0302(19) 0.0319(17) 0.0026(14) 0.0055(13) 0.0009(14) C20 0.0234(15) 0.0235(17) 0.0221(15) 0.0027(12) 0.0023(12) 0.0004(13) C21 0.0249(16) 0.0234(17) 0.0311(16) -0.0033(13) 0.0027(13) -0.0008(13) C22 0.0200(15) 0.0283(18) 0.0294(16) -0.0016(13) -0.0002(12) -0.0031(13) C23 0.0239(16) 0.0296(19) 0.0314(17) -0.0020(14) -0.0010(13) -0.0018(14) C24 0.0251(17) 0.035(2) 0.0345(18) 0.0100(15) -0.0015(14) -0.0023(14) C25 0.0342(18) 0.047(2) 0.0264(17) 0.0014(16) 0.0018(14) -0.0075(16) C26 0.0329(18) 0.045(2) 0.0303(18) -0.0088(16) 0.0005(14) -0.0035(16) C27 0.0255(16) 0.0325(19) 0.0331(17) -0.0035(14) 0.0019(13) -0.0023(14) C28 0.0321(17) 0.0270(18) 0.0354(18) -0.0080(14) -0.0005(14) -0.0031(14) C29 0.0275(16) 0.0241(17) 0.0314(16) -0.0014(13) 0.0060(13) -0.0004(14) C30 0.042(2) 0.0256(18) 0.0383(19) -0.0047(14) 0.0092(16) -0.0011(16) C31 0.0282(17) 0.0292(19) 0.0438(19) 0.0035(15) 0.0064(15) 0.0045(15) C32 0.0248(16) 0.0319(19) 0.0312(17) 0.0086(14) 0.0044(13) 0.0005(14) C33 0.0282(16) 0.0256(17) 0.0276(16) 0.0011(13) 0.0049(13) -0.0018(14) C34 0.0252(16) 0.0242(17) 0.0286(16) 0.0018(13) 0.0052(13) -0.0012(13) C35 0.0243(16) 0.0296(18) 0.0302(16) 0.0063(14) -0.0012(13) 0.0010(14) C36 0.0282(17) 0.036(2) 0.0292(17) 0.0072(14) 0.0007(13) 0.0001(15) C37 0.0314(18) 0.046(2) 0.0344(18) 0.0125(16) -0.0002(15) -0.0009(16) C38 0.0315(19) 0.037(2) 0.054(2) 0.0181(18) -0.0012(16) -0.0061(16) C39 0.0363(19) 0.0263(19) 0.051(2) 0.0032(16) -0.0056(16) -0.0057(16) C40 0.0318(17) 0.0257(18) 0.0350(18) 0.0002(14) -0.0020(14) -0.0028(14) C41 0.047(2) 0.030(2) 0.056(2) 0.0023(17) -0.0059(18) -0.0083(17) C42 0.045(2) 0.0233(19) 0.042(2) 0.0048(15) -0.0005(16) -0.0014(16) C43 0.042(2) 0.040(2) 0.056(2) -0.0019(18) 0.0114(18) -0.0009(17) _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 C4 1.382(3) . ? O1 H1 0.91(4) . ? O2 C12 1.390(3) . ? O2 H2 0.85(4) . ? O3 C24 1.380(4) . ? O3 H3 0.99(4) . ? O4 C32 1.392(4) . ? O4 H4 1.00(4) . ? O5 C42 1.227(4) . ? C1 C2 1.526(4) . ? C1 C14 1.527(4) . ? C1 C15 1.534(4) . ? C1 H1A 1.0000 . ? C2 C3 1.389(4) . ? C2 C7 1.399(4) . ? C3 C4 1.390(4) . ? C3 H3A 0.9500 . ? C4 C5 1.384(4) . ? C5 C6 1.393(4) . ? C5 H5 0.9500 . ? C6 C7 1.388(4) . ? C6 H6 0.9500 . ? C7 C8 1.521(4) . ? C8 C20 1.525(4) . ? C8 C9 1.531(4) . ? C8 H8 1.0000 . ? C9 C10 1.386(4) . ? C9 C14 1.397(4) . ? C10 C11 1.393(4) . ? C10 H10 0.9500 . ? C11 C12 1.382(4) . ? C11 H11 0.9500 . ? C12 C13 1.399(4) . ? C13 C14 1.387(4) . ? C13 H13 0.9500 . ? C15 C16 1.385(4) . ? C15 C20 1.403(4) . ? C16 C17 1.391(4) . ? C16 H16 0.9500 . ? C17 C18 1.388(5) . ? C17 H17 0.9500 . ? C18 C19 1.396(4) . ? C18 H18 0.9500 . ? C19 C20 1.379(4) . ? C19 H19 0.9500 . ? C21 C22 1.528(4) . ? C21 C34 1.528(4) . ? C21 C35 1.532(4) . ? C21 H21 1.0000 . ? C22 C23 1.386(4) . ? C22 C27 1.408(4) . ? C23 C24 1.398(4) . ? C23 H23 0.9500 . ? C24 C25 1.391(5) . ? C25 C26 1.392(5) . ? C25 H25 0.9500 . ? C26 C27 1.381(4) . ? C26 H26 0.9500 . ? C27 C28 1.523(4) . ? C28 C29 1.530(4) . ? C28 C40 1.532(4) . ? C28 H28 1.0000 . ? C29 C30 1.383(4) . ? C29 C34 1.406(4) . ? C30 C31 1.396(4) . ? C30 H30 0.9500 . ? C31 C32 1.386(4) . ? C31 H31 0.9500 . ? C32 C33 1.395(4) . ? C33 C34 1.383(4) . ? C33 H33 0.9500 . ? C35 C36 1.377(4) . ? C35 C40 1.409(4) . ? C36 C37 1.402(4) . ? C36 H36 0.9500 . ? C37 C38 1.382(5) . ? C37 H37 0.9500 . ? C38 C39 1.393(5) . ? C38 H38 0.9500 . ? C39 C40 1.385(4) . ? C39 H39 0.9500 . ? C41 C42 1.479(5) . ? C41 H41A 0.9800 . ? C41 H41B 0.9800 . ? C41 H41C 0.9800 . ? C42 C43 1.491(5) . ? C43 H43A 0.9800 . ? C43 H43B 0.9800 . ? C43 H43C 0.9800 . ? 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 C4 O1 H1 113(2) . . ? C12 O2 H2 110(2) . . ? C24 O3 H3 107(2) . . ? C32 O4 H4 110(2) . . ? C2 C1 C14 106.1(2) . . ? C2 C1 C15 106.2(2) . . ? C14 C1 C15 103.6(2) . . ? C2 C1 H1A 113.4 . . ? C14 C1 H1A 113.4 . . ? C15 C1 H1A 113.4 . . ? C3 C2 C7 120.9(3) . . ? C3 C2 C1 125.9(3) . . ? C7 C2 C1 113.2(2) . . ? C2 C3 C4 118.9(3) . . ? C2 C3 H3A 120.6 . . ? C4 C3 H3A 120.6 . . ? O1 C4 C5 121.4(3) . . ? O1 C4 C3 117.7(3) . . ? C5 C4 C3 120.8(3) . . ? C4 C5 C6 120.0(3) . . ? C4 C5 H5 120.0 . . ? C6 C5 H5 120.0 . . ? C7 C6 C5 119.9(3) . . ? C7 C6 H6 120.0 . . ? C5 C6 H6 120.0 . . ? C6 C7 C2 119.4(3) . . ? C6 C7 C8 127.2(2) . . ? C2 C7 C8 113.4(2) . . ? C7 C8 C20 106.4(2) . . ? C7 C8 C9 106.5(2) . . ? C20 C8 C9 104.2(2) . . ? C7 C8 H8 113.0 . . ? C20 C8 H8 113.0 . . ? C9 C8 H8 113.0 . . ? C10 C9 C14 119.7(3) . . ? C10 C9 C8 127.4(3) . . ? C14 C9 C8 112.9(2) . . ? C9 C10 C11 119.9(3) . . ? C9 C10 H10 120.1 . . ? C11 C10 H10 120.1 . . ? C12 C11 C10 119.7(3) . . ? C12 C11 H11 120.1 . . ? C10 C11 H11 120.1 . . ? C11 C12 O2 117.7(3) . . ? C11 C12 C13 121.4(3) . . ? O2 C12 C13 120.9(3) . . ? C14 C13 C12 118.0(3) . . ? C14 C13 H13 121.0 . . ? C12 C13 H13 121.0 . . ? C13 C14 C9 121.2(3) . . ? C13 C14 C1 125.1(3) . . ? C9 C14 C1 113.6(2) . . ? C16 C15 C20 120.4(3) . . ? C16 C15 C1 126.0(3) . . ? C20 C15 C1 113.4(2) . . ? C15 C16 C17 119.3(3) . . ? C15 C16 H16 120.4 . . ? C17 C16 H16 120.4 . . ? C18 C17 C16 120.6(3) . . ? C18 C17 H17 119.7 . . ? C16 C17 H17 119.7 . . ? C17 C18 C19 120.0(3) . . ? C17 C18 H18 120.0 . . ? C19 C18 H18 120.0 . . ? C20 C19 C18 119.7(3) . . ? C20 C19 H19 120.1 . . ? C18 C19 H19 120.1 . . ? C19 C20 C15 120.0(3) . . ? C19 C20 C8 127.1(3) . . ? C15 C20 C8 112.8(2) . . ? C22 C21 C34 107.0(2) . . ? C22 C21 C35 106.0(2) . . ? C34 C21 C35 103.7(2) . . ? C22 C21 H21 113.2 . . ? C34 C21 H21 113.2 . . ? C35 C21 H21 113.2 . . ? C23 C22 C27 120.6(3) . . ? C23 C22 C21 126.0(3) . . ? C27 C22 C21 113.4(3) . . ? C22 C23 C24 118.9(3) . . ? C22 C23 H23 120.6 . . ? C24 C23 H23 120.6 . . ? O3 C24 C25 117.0(3) . . ? O3 C24 C23 122.1(3) . . ? C25 C24 C23 120.9(3) . . ? C24 C25 C26 119.6(3) . . ? C24 C25 H25 120.2 . . ? C26 C25 H25 120.2 . . ? C27 C26 C25 120.3(3) . . ? C27 C26 H26 119.8 . . ? C25 C26 H26 119.8 . . ? C26 C27 C22 119.7(3) . . ? C26 C27 C28 127.8(3) . . ? C22 C27 C28 112.5(3) . . ? C27 C28 C29 107.5(2) . . ? C27 C28 C40 106.4(3) . . ? C29 C28 C40 104.0(2) . . ? C27 C28 H28 112.7 . . ? C29 C28 H28 112.7 . . ? C40 C28 H28 112.7 . . ? C30 C29 C34 119.9(3) . . ? C30 C29 C28 127.3(3) . . ? C34 C29 C28 112.7(3) . . ? C29 C30 C31 120.1(3) . . ? C29 C30 H30 120.0 . . ? C31 C30 H30 120.0 . . ? C32 C31 C30 119.5(3) . . ? C32 C31 H31 120.3 . . ? C30 C31 H31 120.3 . . ? C31 C32 O4 121.4(3) . . ? C31 C32 C33 121.1(3) . . ? O4 C32 C33 117.5(3) . . ? C34 C33 C32 119.1(3) . . ? C34 C33 H33 120.5 . . ? C32 C33 H33 120.5 . . ? C33 C34 C29 120.3(3) . . ? C33 C34 C21 126.2(3) . . ? C29 C34 C21 113.2(3) . . ? C36 C35 C40 120.4(3) . . ? C36 C35 C21 126.4(3) . . ? C40 C35 C21 113.1(3) . . ? C35 C36 C37 119.2(3) . . ? C35 C36 H36 120.4 . . ? C37 C36 H36 120.4 . . ? C38 C37 C36 120.5(3) . . ? C38 C37 H37 119.8 . . ? C36 C37 H37 119.8 . . ? C37 C38 C39 120.3(3) . . ? C37 C38 H38 119.9 . . ? C39 C38 H38 119.9 . . ? C40 C39 C38 119.7(3) . . ? C40 C39 H39 120.1 . . ? C38 C39 H39 120.1 . . ? C39 C40 C35 119.8(3) . . ? C39 C40 C28 127.4(3) . . ? C35 C40 C28 112.6(3) . . ? C42 C41 H41A 109.5 . . ? C42 C41 H41B 109.5 . . ? H41A C41 H41B 109.5 . . ? C42 C41 H41C 109.5 . . ? H41A C41 H41C 109.5 . . ? H41B C41 H41C 109.5 . . ? O5 C42 C41 121.3(3) . . ? O5 C42 C43 120.9(3) . . ? C41 C42 C43 117.9(3) . . ? C42 C43 H43A 109.5 . . ? C42 C43 H43B 109.5 . . ? H43A C43 H43B 109.5 . . ? C42 C43 H43C 109.5 . . ? H43A C43 H43C 109.5 . . ? H43B C43 H43C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C14 C1 C2 C3 -124.8(3) . . . . ? C15 C1 C2 C3 125.5(3) . . . . ? C14 C1 C2 C7 56.0(3) . . . . ? C15 C1 C2 C7 -53.7(3) . . . . ? C7 C2 C3 C4 1.9(4) . . . . ? C1 C2 C3 C4 -177.3(3) . . . . ? C2 C3 C4 O1 178.6(2) . . . . ? C2 C3 C4 C5 0.0(4) . . . . ? O1 C4 C5 C6 179.5(3) . . . . ? C3 C4 C5 C6 -1.9(4) . . . . ? C4 C5 C6 C7 1.9(4) . . . . ? C5 C6 C7 C2 -0.1(4) . . . . ? C5 C6 C7 C8 179.0(3) . . . . ? C3 C2 C7 C6 -1.9(4) . . . . ? C1 C2 C7 C6 177.4(2) . . . . ? C3 C2 C7 C8 179.0(2) . . . . ? C1 C2 C7 C8 -1.8(3) . . . . ? C6 C7 C8 C20 -122.4(3) . . . . ? C2 C7 C8 C20 56.7(3) . . . . ? C6 C7 C8 C9 126.9(3) . . . . ? C2 C7 C8 C9 -54.0(3) . . . . ? C7 C8 C9 C10 -127.5(3) . . . . ? C20 C8 C9 C10 120.3(3) . . . . ? C7 C8 C9 C14 55.9(3) . . . . ? C20 C8 C9 C14 -56.3(3) . . . . ? C14 C9 C10 C11 1.2(4) . . . . ? C8 C9 C10 C11 -175.3(3) . . . . ? C9 C10 C11 C12 0.1(4) . . . . ? C10 C11 C12 O2 178.8(3) . . . . ? C10 C11 C12 C13 -0.9(4) . . . . ? C11 C12 C13 C14 0.4(4) . . . . ? O2 C12 C13 C14 -179.3(3) . . . . ? C12 C13 C14 C9 0.9(4) . . . . ? C12 C13 C14 C1 177.2(3) . . . . ? C10 C9 C14 C13 -1.7(4) . . . . ? C8 C9 C14 C13 175.2(3) . . . . ? C10 C9 C14 C1 -178.4(3) . . . . ? C8 C9 C14 C1 -1.5(3) . . . . ? C2 C1 C14 C13 129.4(3) . . . . ? C15 C1 C14 C13 -119.1(3) . . . . ? C2 C1 C14 C9 -54.1(3) . . . . ? C15 C1 C14 C9 57.5(3) . . . . ? C2 C1 C15 C16 -129.1(3) . . . . ? C14 C1 C15 C16 119.4(3) . . . . ? C2 C1 C15 C20 55.5(3) . . . . ? C14 C1 C15 C20 -56.0(3) . . . . ? C20 C15 C16 C17 0.0(4) . . . . ? C1 C15 C16 C17 -175.1(3) . . . . ? C15 C16 C17 C18 -0.1(5) . . . . ? C16 C17 C18 C19 0.0(5) . . . . ? C17 C18 C19 C20 0.1(5) . . . . ? C18 C19 C20 C15 -0.2(4) . . . . ? C18 C19 C20 C8 176.3(3) . . . . ? C16 C15 C20 C19 0.1(4) . . . . ? C1 C15 C20 C19 175.8(3) . . . . ? C16 C15 C20 C8 -176.8(3) . . . . ? C1 C15 C20 C8 -1.2(3) . . . . ? C7 C8 C20 C19 128.7(3) . . . . ? C9 C8 C20 C19 -119.1(3) . . . . ? C7 C8 C20 C15 -54.6(3) . . . . ? C9 C8 C20 C15 57.6(3) . . . . ? C34 C21 C22 C23 -126.6(3) . . . . ? C35 C21 C22 C23 123.2(3) . . . . ? C34 C21 C22 C27 54.5(3) . . . . ? C35 C21 C22 C27 -55.6(3) . . . . ? C27 C22 C23 C24 -0.7(4) . . . . ? C21 C22 C23 C24 -179.5(3) . . . . ? C22 C23 C24 O3 -179.1(3) . . . . ? C22 C23 C24 C25 0.6(5) . . . . ? O3 C24 C25 C26 179.5(3) . . . . ? C23 C24 C25 C26 -0.3(5) . . . . ? C24 C25 C26 C27 0.0(5) . . . . ? C25 C26 C27 C22 -0.1(5) . . . . ? C25 C26 C27 C28 179.0(3) . . . . ? C23 C22 C27 C26 0.5(5) . . . . ? C21 C22 C27 C26 179.4(3) . . . . ? C23 C22 C27 C28 -178.8(3) . . . . ? C21 C22 C27 C28 0.1(4) . . . . ? C26 C27 C28 C29 125.8(3) . . . . ? C22 C27 C28 C29 -55.1(3) . . . . ? C26 C27 C28 C40 -123.3(3) . . . . ? C22 C27 C28 C40 55.9(3) . . . . ? C27 C28 C29 C30 -128.7(3) . . . . ? C40 C28 C29 C30 118.7(3) . . . . ? C27 C28 C29 C34 55.1(3) . . . . ? C40 C28 C29 C34 -57.6(3) . . . . ? C34 C29 C30 C31 1.5(5) . . . . ? C28 C29 C30 C31 -174.5(3) . . . . ? C29 C30 C31 C32 -0.5(5) . . . . ? C30 C31 C32 O4 178.1(3) . . . . ? C30 C31 C32 C33 -0.8(5) . . . . ? C31 C32 C33 C34 1.1(4) . . . . ? O4 C32 C33 C34 -177.9(3) . . . . ? C32 C33 C34 C29 -0.1(4) . . . . ? C32 C33 C34 C21 174.5(3) . . . . ? C30 C29 C34 C33 -1.2(4) . . . . ? C28 C29 C34 C33 175.4(3) . . . . ? C30 C29 C34 C21 -176.4(3) . . . . ? C28 C29 C34 C21 0.1(4) . . . . ? C22 C21 C34 C33 130.5(3) . . . . ? C35 C21 C34 C33 -117.7(3) . . . . ? C22 C21 C34 C29 -54.6(3) . . . . ? C35 C21 C34 C29 57.2(3) . . . . ? C22 C21 C35 C36 -128.2(3) . . . . ? C34 C21 C35 C36 119.3(3) . . . . ? C22 C21 C35 C40 55.1(3) . . . . ? C34 C21 C35 C40 -57.4(3) . . . . ? C40 C35 C36 C37 -0.2(4) . . . . ? C21 C35 C36 C37 -176.6(3) . . . . ? C35 C36 C37 C38 0.1(5) . . . . ? C36 C37 C38 C39 0.1(5) . . . . ? C37 C38 C39 C40 -0.1(5) . . . . ? C38 C39 C40 C35 0.0(5) . . . . ? C38 C39 C40 C28 176.2(3) . . . . ? C36 C35 C40 C39 0.2(5) . . . . ? C21 C35 C40 C39 177.0(3) . . . . ? C36 C35 C40 C28 -176.6(3) . . . . ? C21 C35 C40 C28 0.3(4) . . . . ? C27 C28 C40 C39 127.4(3) . . . . ? C29 C28 C40 C39 -119.2(3) . . . . ? C27 C28 C40 C35 -56.2(3) . . . . ? C29 C28 C40 C35 57.2(3) . . . . ? 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 O4 H4 O2 1.00(4) 1.72(4) 2.701(3) 166(3) 3_666 O3 H3 O4 0.99(4) 1.77(4) 2.747(3) 170(4) 3_676 O2 H2 O1 0.85(4) 1.86(4) 2.705(3) 175(4) 2_545 O1 H1 O5 0.91(4) 1.82(4) 2.699(3) 162(3) 1_565 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.904 _refine_diff_density_min -0.221 _refine_diff_density_rms 0.056 # Attachment '1b.cif' data_61225d _database_code_depnum_ccdc_archive 'CCDC 760761' #TrackingRef '1b.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C58 H46 N3 O5' _chemical_formula_weight 864.98 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 22.069(7) _cell_length_b 8.189(3) _cell_length_c 28.795(9) _cell_angle_alpha 90.00 _cell_angle_beta 109.128(5) _cell_angle_gamma 90.00 _cell_volume 4917(3) _cell_formula_units_Z 4 _cell_measurement_temperature 294(2) _cell_measurement_reflns_used 6453 _cell_measurement_theta_min 2.60 _cell_measurement_theta_max 24.48 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas NONE _exptl_crystal_density_diffrn 1.169 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1820 _exptl_absorpt_coefficient_mu 0.075 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9823 _exptl_absorpt_correction_T_max 0.9852 _exptl_absorpt_process_details sadabs _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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number . _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% . _diffrn_reflns_number 24130 _diffrn_reflns_av_R_equivalents 0.0435 _diffrn_reflns_av_sigmaI/netI 0.0511 _diffrn_reflns_limit_h_min -25 _diffrn_reflns_limit_h_max 26 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -34 _diffrn_reflns_limit_l_max 33 _diffrn_reflns_theta_min 2.60 _diffrn_reflns_theta_max 25.02 _reflns_number_total 8563 _reflns_number_gt 5052 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1128P)^2^+1.5277P] 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 8563 _refine_ls_number_parameters 655 _refine_ls_number_restraints 90 _refine_ls_R_factor_all 0.1178 _refine_ls_R_factor_gt 0.0672 _refine_ls_wR_factor_ref 0.2138 _refine_ls_wR_factor_gt 0.1726 _refine_ls_goodness_of_fit_ref 1.038 _refine_ls_restrained_S_all 1.052 _refine_ls_shift/su_max 0.003 _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 0.23518(13) -0.2351(3) 0.47667(9) 0.0654(7) Uani 1 1 d . . . H1 H 0.2503 -0.3255 0.4750 0.098 Uiso 1 1 calc R . . O2 O -0.07801(14) 0.3906(4) 0.37270(12) 0.0866(9) Uani 1 1 d . . . H2 H -0.0552 0.4579 0.3916 0.130 Uiso 1 1 calc R . . O3 O 0.67910(14) 0.9048(3) 0.37837(8) 0.0696(7) Uani 1 1 d . . . H3 H 0.6983 0.9791 0.3702 0.104 Uiso 1 1 calc R . . O4 O 0.45190(11) 1.0244(3) 0.06308(8) 0.0566(6) Uani 1 1 d . . . H4 H 0.4812 1.0864 0.0634 0.085 Uiso 1 1 calc R . . N1 N 0.46577(14) -0.2462(3) 0.44902(10) 0.0543(7) Uani 1 1 d . . . N2 N 0.28503(14) 0.4435(4) 0.47766(11) 0.0601(8) Uani 1 1 d . . . C1 C 0.19004(15) -0.0189(4) 0.42133(12) 0.0481(8) Uani 1 1 d . . . H1A H 0.2110 0.0554 0.4457 0.058 Uiso 1 1 calc R . . C2 C 0.19730(16) -0.1864(4) 0.43030(12) 0.0507(8) Uani 1 1 d . . . C3 C 0.16611(17) -0.2961(4) 0.39393(14) 0.0569(9) Uani 1 1 d . . . H3A H 0.1706 -0.4076 0.4003 0.068 Uiso 1 1 calc R . . C4 C 0.12812(17) -0.2419(4) 0.34803(14) 0.0574(9) Uani 1 1 d . . . H4A H 0.1079 -0.3169 0.3236 0.069 Uiso 1 1 calc R . . C5 C 0.12026(15) -0.0761(4) 0.33857(12) 0.0491(8) Uani 1 1 d . . . C6 C 0.15114(15) 0.0359(4) 0.37557(11) 0.0449(7) Uani 1 1 d . . . C7 C 0.13341(15) 0.2135(4) 0.36074(11) 0.0462(8) Uani 1 1 d . . . H7 H 0.1548 0.2912 0.3869 0.055 Uiso 1 1 calc R . . C8 C 0.06023(15) 0.2200(4) 0.34616(12) 0.0468(8) Uani 1 1 d . . . C9 C 0.02509(17) 0.3173(4) 0.36666(13) 0.0537(9) Uani 1 1 d . . . H9 H 0.0454 0.3950 0.3902 0.064 Uiso 1 1 calc R . . C10 C -0.04123(18) 0.2987(4) 0.35199(14) 0.0596(9) Uani 1 1 d . . . C11 C -0.07160(18) 0.1865(5) 0.31620(15) 0.0663(10) Uani 1 1 d . . . H11 H -0.1159 0.1748 0.3066 0.080 Uiso 1 1 calc R . . C12 C -0.03633(18) 0.0908(4) 0.29449(14) 0.0617(10) Uani 1 1 d . . . H12 H -0.0571 0.0162 0.2701 0.074 Uiso 1 1 calc R . . C13 C 0.03007(16) 0.1068(4) 0.30929(13) 0.0519(8) Uani 1 1 d . . . C14 C 0.07694(17) 0.0071(4) 0.29195(12) 0.0548(9) Uani 1 1 d . . . H14 H 0.0555 -0.0705 0.2658 0.066 Uiso 1 1 calc R . . C15 C 0.11893(17) 0.1312(4) 0.27645(12) 0.0539(9) Uani 1 1 d . . . C16 C 0.1280(2) 0.1439(5) 0.23156(14) 0.0704(11) Uani 1 1 d . . . H16 H 0.1087 0.0696 0.2067 0.084 Uiso 1 1 calc R . . C17 C 0.1664(2) 0.2692(6) 0.22356(17) 0.0779(12) Uani 1 1 d . . . H17 H 0.1729 0.2768 0.1933 0.093 Uiso 1 1 calc R . . C18 C 0.19463(19) 0.3807(5) 0.25944(16) 0.0678(10) Uani 1 1 d . . . H18 H 0.2194 0.4646 0.2534 0.081 Uiso 1 1 calc R . . C19 C 0.18605(16) 0.3679(4) 0.30488(14) 0.0563(9) Uani 1 1 d . . . H19 H 0.2056 0.4428 0.3295 0.068 Uiso 1 1 calc R . . C20 C 0.14852(16) 0.2438(4) 0.31373(12) 0.0496(8) Uani 1 1 d . . . C21 C 0.65364(15) 0.8416(4) 0.29196(11) 0.0440(7) Uani 1 1 d . . . H21 H 0.6827 0.9189 0.2884 0.053 Uiso 1 1 calc R . . C22 C 0.64491(16) 0.8175(4) 0.33771(11) 0.0459(8) Uani 1 1 d . . . C23 C 0.60143(17) 0.7028(4) 0.34279(12) 0.0529(9) Uani 1 1 d . . . H23 H 0.5959 0.6882 0.3732 0.064 Uiso 1 1 calc R . . C24 C 0.56589(16) 0.6091(4) 0.30272(12) 0.0503(8) Uani 1 1 d . . . H24 H 0.5368 0.5319 0.3063 0.060 Uiso 1 1 calc R . . C25 C 0.57408(15) 0.6315(4) 0.25737(11) 0.0422(7) Uani 1 1 d . . . C26 C 0.61819(14) 0.7481(3) 0.25249(11) 0.0402(7) Uani 1 1 d . . . C27 C 0.62416(14) 0.7512(3) 0.20109(10) 0.0383(7) Uani 1 1 d . . . H27 H 0.6553 0.8320 0.1978 0.046 Uiso 1 1 calc R . . C28 C 0.55602(14) 0.7805(3) 0.16519(10) 0.0380(7) Uani 1 1 d . . . C29 C 0.53760(14) 0.9023(3) 0.13006(10) 0.0382(7) Uani 1 1 d . . . H29 H 0.5673 0.9794 0.1274 0.046 Uiso 1 1 calc R . . C30 C 0.47410(15) 0.9090(4) 0.09851(11) 0.0413(7) Uani 1 1 d . . . C31 C 0.43077(16) 0.7922(4) 0.10349(12) 0.0509(8) Uani 1 1 d . . . H31 H 0.3885 0.7958 0.0827 0.061 Uiso 1 1 calc R . . C32 C 0.44949(15) 0.6707(4) 0.13895(12) 0.0476(8) Uani 1 1 d . . . H32 H 0.4198 0.5940 0.1418 0.057 Uiso 1 1 calc R . . C33 C 0.51257(15) 0.6636(4) 0.17023(11) 0.0422(7) Uani 1 1 d . . . C34 C 0.54197(15) 0.5372(4) 0.20977(11) 0.0447(8) Uani 1 1 d . . . H34 H 0.5107 0.4568 0.2130 0.054 Uiso 1 1 calc R . . C35 C 0.59727(15) 0.4596(4) 0.19659(11) 0.0429(7) Uani 1 1 d . . . C36 C 0.60751(18) 0.2958(4) 0.19021(12) 0.0554(9) Uani 1 1 d . . . H36 H 0.5791 0.2177 0.1944 0.066 Uiso 1 1 calc R . . C37 C 0.66037(18) 0.2488(4) 0.17758(14) 0.0625(10) Uani 1 1 d . . . H37 H 0.6669 0.1386 0.1730 0.075 Uiso 1 1 calc R . . C38 C 0.70317(18) 0.3614(4) 0.17173(14) 0.0603(9) Uani 1 1 d . . . H38 H 0.7381 0.3276 0.1629 0.072 Uiso 1 1 calc R . . C39 C 0.69429(15) 0.5271(4) 0.17905(11) 0.0477(8) Uani 1 1 d . . . H39 H 0.7236 0.6039 0.1757 0.057 Uiso 1 1 calc R . . C40 C 0.64132(14) 0.5759(3) 0.19139(10) 0.0396(7) Uani 1 1 d . . . C41 C 0.47502(17) -0.0977(4) 0.43336(12) 0.0530(8) Uani 1 1 d . . . H41 H 0.5059 -0.0859 0.4180 0.064 Uiso 1 1 calc R . . C42 C 0.44154(16) 0.0386(4) 0.43856(11) 0.0486(8) Uani 1 1 d . . . H42 H 0.4500 0.1390 0.4269 0.058 Uiso 1 1 calc R . . C43 C 0.39500(15) 0.0264(4) 0.46133(10) 0.0415(7) Uani 1 1 d . . . C44 C 0.38504(17) -0.1286(4) 0.47807(12) 0.0525(8) Uani 1 1 d . . . H44 H 0.3543 -0.1438 0.4933 0.063 Uiso 1 1 calc R . . C45 C 0.42139(18) -0.2587(4) 0.47166(13) 0.0560(9) Uani 1 1 d . . . H45 H 0.4148 -0.3604 0.4836 0.067 Uiso 1 1 calc R . . C46 C 0.35723(15) 0.1701(4) 0.46750(11) 0.0430(7) Uani 1 1 d . . . C47 C 0.33601(16) 0.1885(4) 0.50770(12) 0.0507(8) Uani 1 1 d . . . H47 H 0.3455 0.1093 0.5322 0.061 Uiso 1 1 calc R . . C48 C 0.30079(17) 0.3250(5) 0.51110(13) 0.0587(9) Uani 1 1 d . . . H48 H 0.2873 0.3345 0.5384 0.070 Uiso 1 1 calc R . . C49 C 0.30561(18) 0.4267(4) 0.43917(14) 0.0611(9) Uani 1 1 d . . . H49 H 0.2954 0.5081 0.4153 0.073 Uiso 1 1 calc R . . C50 C 0.34115(17) 0.2956(4) 0.43285(12) 0.0535(9) Uani 1 1 d . . . H50 H 0.3545 0.2907 0.4054 0.064 Uiso 1 1 calc R . . N3 N 1.0057(3) 0.1438(7) 0.0743(3) 0.0574(16) Uani 0.50 1 d PU . . N4 N 0.8289(4) 0.7907(13) -0.0702(4) 0.099(3) Uani 0.50 1 d PU . . C51 C 0.9732(6) 0.1230(10) 0.0376(5) 0.089(3) Uani 0.50 1 d PU . . H51 H 0.9701 0.0151 0.0270 0.107 Uiso 0.50 1 calc PR . . C52 C 0.9315(4) 0.2446(11) 0.0003(3) 0.083(3) Uani 0.50 1 d PU . . H52 H 0.9068 0.2148 -0.0314 0.100 Uiso 0.50 1 calc PR . . C53 C 0.9338(3) 0.4003(8) 0.0176(2) 0.0419(15) Uani 0.50 1 d PU . . C54 C 0.9718(3) 0.4210(8) 0.0664(2) 0.0463(15) Uani 0.50 1 d PU . . H54 H 0.9741 0.5237 0.0807 0.056 Uiso 0.50 1 calc PR . . C55 C 1.0049(3) 0.2979(8) 0.0935(3) 0.0521(16) Uani 0.50 1 d PU . . H55 H 1.0283 0.3167 0.1264 0.063 Uiso 0.50 1 calc PR . . C56 C 0.8973(3) 0.5377(9) -0.0123(2) 0.0487(16) Uani 0.50 1 d PU . . C57 C 0.8663(4) 0.5165(13) -0.0623(3) 0.088(3) Uani 0.50 1 d PU . . H57 H 0.8668 0.4171 -0.0777 0.106 Uiso 0.50 1 calc PR . . C58 C 0.8338(5) 0.6550(18) -0.0885(4) 0.101(3) Uani 0.50 1 d PU . . H58 H 0.8145 0.6438 -0.1222 0.121 Uiso 0.50 1 calc PR . . C59 C 0.8550(5) 0.8128(13) -0.0220(4) 0.099(3) Uani 0.50 1 d PU . . H59 H 0.8500 0.9114 -0.0077 0.119 Uiso 0.50 1 calc PR . . C60 C 0.8906(4) 0.6842(11) 0.0070(3) 0.079(2) Uani 0.50 1 d PU . . H60 H 0.9101 0.7010 0.0405 0.095 Uiso 0.50 1 calc PR . . O5 O 0.2518(2) 0.6435(4) 0.15721(13) 0.1192(13) Uani 1 1 d . . . C61 C 0.2487(3) 0.9101(7) 0.1867(2) 0.1206(19) Uani 1 1 d U . . H61A H 0.2440 0.8538 0.2145 0.181 Uiso 1 1 calc R . . H61B H 0.2119 0.9780 0.1722 0.181 Uiso 1 1 calc R . . H61C H 0.2866 0.9767 0.1971 0.181 Uiso 1 1 calc R . . C62 C 0.2543(2) 0.7902(5) 0.15018(16) 0.0745(12) Uani 1 1 d U . . C63 C 0.2606(4) 0.8563(9) 0.1052(2) 0.148(2) Uani 1 1 d U . . H63A H 0.3015 0.9093 0.1124 0.222 Uiso 1 1 calc R . . H63B H 0.2270 0.9339 0.0912 0.222 Uiso 1 1 calc R . . H63C H 0.2576 0.7692 0.0822 0.222 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 0.0727(18) 0.0590(16) 0.0586(15) 0.0045(12) 0.0134(13) 0.0132(13) O2 0.0724(19) 0.092(2) 0.103(2) 0.0069(17) 0.0388(18) 0.0206(16) O3 0.083(2) 0.0754(18) 0.0484(15) -0.0086(13) 0.0183(14) -0.0028(14) O4 0.0584(15) 0.0491(14) 0.0562(14) 0.0057(12) 0.0105(12) 0.0015(11) N1 0.0664(19) 0.0458(17) 0.0455(16) -0.0026(13) 0.0110(15) 0.0031(13) N2 0.0596(19) 0.0575(18) 0.0588(19) 0.0011(16) 0.0134(16) 0.0075(14) C1 0.0447(19) 0.0420(18) 0.053(2) -0.0074(15) 0.0102(16) 0.0017(14) C2 0.0485(19) 0.049(2) 0.052(2) 0.0002(17) 0.0138(16) 0.0076(15) C3 0.064(2) 0.0381(18) 0.067(2) -0.0016(17) 0.0185(19) 0.0071(16) C4 0.058(2) 0.0408(19) 0.066(2) -0.0154(17) 0.0107(19) 0.0006(16) C5 0.0489(19) 0.0415(18) 0.051(2) -0.0100(15) 0.0086(16) 0.0014(14) C6 0.0436(18) 0.0382(17) 0.0493(19) -0.0047(15) 0.0104(15) -0.0007(13) C7 0.0484(19) 0.0389(17) 0.0463(18) -0.0084(14) 0.0086(15) -0.0009(14) C8 0.0490(19) 0.0375(17) 0.0500(19) 0.0007(15) 0.0110(16) 0.0034(14) C9 0.057(2) 0.0420(18) 0.060(2) 0.0007(16) 0.0169(18) 0.0046(15) C10 0.054(2) 0.057(2) 0.072(2) 0.015(2) 0.027(2) 0.0155(18) C11 0.044(2) 0.061(2) 0.085(3) 0.016(2) 0.009(2) 0.0045(18) C12 0.055(2) 0.052(2) 0.066(2) 0.0057(18) 0.0027(19) -0.0049(17) C13 0.047(2) 0.0448(19) 0.057(2) -0.0007(16) 0.0069(17) 0.0017(15) C14 0.059(2) 0.0427(18) 0.053(2) -0.0116(16) 0.0042(17) 0.0012(16) C15 0.057(2) 0.050(2) 0.051(2) -0.0042(17) 0.0130(17) 0.0139(16) C16 0.081(3) 0.072(3) 0.055(2) -0.004(2) 0.018(2) 0.019(2) C17 0.082(3) 0.092(3) 0.068(3) 0.019(3) 0.036(2) 0.025(3) C18 0.061(2) 0.069(3) 0.077(3) 0.015(2) 0.028(2) 0.0160(19) C19 0.046(2) 0.050(2) 0.070(2) 0.0021(17) 0.0146(18) 0.0118(15) C20 0.0477(19) 0.0413(18) 0.058(2) -0.0006(16) 0.0151(17) 0.0082(15) C21 0.053(2) 0.0364(16) 0.0427(18) -0.0008(14) 0.0162(15) 0.0013(14) C22 0.053(2) 0.0451(18) 0.0389(18) -0.0031(15) 0.0142(15) 0.0059(15) C23 0.066(2) 0.053(2) 0.0452(19) 0.0069(16) 0.0253(18) 0.0078(17) C24 0.056(2) 0.0464(19) 0.054(2) 0.0076(16) 0.0256(17) -0.0011(15) C25 0.0476(18) 0.0399(17) 0.0428(17) 0.0043(14) 0.0197(15) -0.0018(13) C26 0.0469(18) 0.0352(16) 0.0403(17) 0.0014(14) 0.0168(15) -0.0014(13) C27 0.0459(18) 0.0319(15) 0.0391(16) -0.0024(13) 0.0169(14) -0.0101(13) C28 0.0431(17) 0.0350(16) 0.0392(16) -0.0073(13) 0.0182(14) -0.0075(13) C29 0.0476(18) 0.0294(15) 0.0414(17) -0.0063(13) 0.0199(15) -0.0071(12) C30 0.0464(19) 0.0373(17) 0.0391(17) -0.0064(14) 0.0124(15) 0.0025(13) C31 0.0410(19) 0.053(2) 0.057(2) -0.0078(17) 0.0128(16) -0.0048(15) C32 0.0455(19) 0.0439(18) 0.056(2) -0.0049(16) 0.0202(16) -0.0120(14) C33 0.0464(19) 0.0371(16) 0.0458(18) -0.0050(14) 0.0188(15) -0.0085(13) C34 0.0495(19) 0.0380(16) 0.0497(19) 0.0018(14) 0.0206(16) -0.0120(14) C35 0.0494(19) 0.0362(16) 0.0405(17) -0.0006(14) 0.0111(15) -0.0062(14) C36 0.066(2) 0.0366(18) 0.062(2) -0.0045(16) 0.0175(19) -0.0111(16) C37 0.061(2) 0.0406(19) 0.081(3) -0.0109(18) 0.016(2) 0.0030(17) C38 0.057(2) 0.054(2) 0.071(2) -0.0114(18) 0.0218(19) 0.0055(17) C39 0.0480(19) 0.0465(19) 0.0482(19) -0.0032(15) 0.0150(16) -0.0056(14) C40 0.0452(18) 0.0366(16) 0.0352(16) -0.0013(13) 0.0109(14) -0.0039(13) C41 0.062(2) 0.051(2) 0.0486(19) 0.0006(16) 0.0209(17) 0.0015(17) C42 0.058(2) 0.0419(18) 0.0446(18) 0.0087(15) 0.0152(16) -0.0002(15) C43 0.0470(18) 0.0414(17) 0.0323(16) 0.0019(13) 0.0079(14) -0.0024(14) C44 0.058(2) 0.047(2) 0.053(2) 0.0045(16) 0.0185(17) -0.0067(16) C45 0.066(2) 0.0407(19) 0.056(2) 0.0049(16) 0.0133(19) -0.0077(16) C46 0.0452(18) 0.0420(17) 0.0359(16) 0.0013(14) 0.0052(14) -0.0026(14) C47 0.055(2) 0.054(2) 0.0405(18) 0.0019(15) 0.0124(16) -0.0001(16) C48 0.060(2) 0.066(2) 0.049(2) -0.0052(19) 0.0155(18) 0.0065(18) C49 0.065(2) 0.054(2) 0.059(2) 0.0098(18) 0.0120(19) 0.0070(18) C50 0.060(2) 0.052(2) 0.048(2) 0.0078(16) 0.0162(17) 0.0059(16) N3 0.053(4) 0.055(4) 0.070(4) 0.016(3) 0.027(3) -0.011(3) N4 0.060(4) 0.122(6) 0.106(6) 0.060(5) 0.015(4) -0.009(4) C51 0.120(7) 0.036(4) 0.122(7) -0.011(5) 0.054(6) -0.006(4) C52 0.087(5) 0.092(6) 0.056(4) -0.032(4) 0.003(4) -0.020(4) C53 0.032(3) 0.058(4) 0.044(3) -0.003(3) 0.023(3) -0.010(3) C54 0.049(4) 0.042(3) 0.050(4) -0.017(3) 0.019(3) -0.005(3) C55 0.049(4) 0.048(4) 0.059(4) 0.015(3) 0.018(3) 0.001(3) C56 0.038(3) 0.076(4) 0.034(3) 0.000(3) 0.016(3) -0.025(3) C57 0.079(5) 0.101(6) 0.080(5) 0.011(5) 0.019(4) -0.025(5) C58 0.069(5) 0.152(8) 0.077(6) 0.020(6) 0.016(4) -0.015(6) C59 0.081(6) 0.094(6) 0.118(7) 0.027(5) 0.025(5) -0.006(5) C60 0.079(5) 0.080(5) 0.063(5) 0.030(4) 0.004(4) -0.003(4) O5 0.163(4) 0.077(2) 0.102(3) 0.006(2) 0.022(2) 0.037(2) C61 0.134(5) 0.108(4) 0.115(4) -0.039(3) 0.033(4) -0.001(3) C62 0.067(3) 0.067(3) 0.080(3) 0.002(2) 0.010(2) 0.020(2) C63 0.169(6) 0.157(5) 0.138(5) 0.014(4) 0.077(4) -0.011(4) _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 1.382(4) . ? O1 H1 0.8200 . ? O2 C10 1.378(4) . ? O2 H2 0.8200 . ? O3 C22 1.368(4) . ? O3 H3 0.8200 . ? O4 C30 1.359(4) . ? O4 H4 0.8200 . ? N1 C41 1.336(4) . ? N1 C45 1.347(5) . ? N2 C48 1.331(4) . ? N2 C49 1.336(5) . ? C1 C6 1.390(4) . ? C1 C2 1.395(4) . ? C1 H1A 0.9300 . ? C2 C3 1.380(5) . ? C3 C4 1.386(5) . ? C3 H3A 0.9300 . ? C4 C5 1.384(4) . ? C4 H4A 0.9300 . ? C5 C6 1.402(4) . ? C5 C14 1.529(5) . ? C6 C7 1.530(4) . ? C7 C20 1.517(5) . ? C7 C8 1.531(4) . ? C7 H7 0.9800 . ? C8 C9 1.373(4) . ? C8 C13 1.402(4) . ? C9 C10 1.392(5) . ? C9 H9 0.9300 . ? C10 C11 1.379(5) . ? C11 C12 1.389(5) . ? C11 H11 0.9300 . ? C12 C13 1.392(5) . ? C12 H12 0.9300 . ? C13 C14 1.525(5) . ? C14 C15 1.537(5) . ? C14 H14 0.9800 . ? C15 C16 1.375(5) . ? C15 C20 1.403(5) . ? C16 C17 1.397(6) . ? C16 H16 0.9300 . ? C17 C18 1.366(6) . ? C17 H17 0.9300 . ? C18 C19 1.386(5) . ? C18 H18 0.9300 . ? C19 C20 1.386(5) . ? C19 H19 0.9300 . ? C21 C26 1.381(4) . ? C21 C22 1.406(4) . ? C21 H21 0.9300 . ? C22 C23 1.384(5) . ? C23 C24 1.394(5) . ? C23 H23 0.9300 . ? C24 C25 1.388(4) . ? C24 H24 0.9300 . ? C25 C26 1.404(4) . ? C25 C34 1.530(4) . ? C26 C27 1.528(4) . ? C27 C40 1.534(4) . ? C27 C28 1.539(4) . ? C27 H27 0.9800 . ? C28 C29 1.383(4) . ? C28 C33 1.396(4) . ? C29 C30 1.399(4) . ? C29 H29 0.9300 . ? C30 C31 1.392(4) . ? C31 C32 1.388(5) . ? C31 H31 0.9300 . ? C32 C33 1.390(4) . ? C32 H32 0.9300 . ? C33 C34 1.518(4) . ? C34 C35 1.530(4) . ? C34 H34 0.9800 . ? C35 C36 1.383(4) . ? C35 C40 1.403(4) . ? C36 C37 1.385(5) . ? C36 H36 0.9300 . ? C37 C38 1.369(5) . ? C37 H37 0.9300 . ? C38 C39 1.397(5) . ? C38 H38 0.9300 . ? C39 C40 1.387(4) . ? C39 H39 0.9300 . ? C41 C42 1.374(4) . ? C41 H41 0.9300 . ? C42 C43 1.392(4) . ? C42 H42 0.9300 . ? C43 C44 1.400(4) . ? C43 C46 1.486(4) . ? C44 C45 1.382(5) . ? C44 H44 0.9300 . ? C45 H45 0.9300 . ? C46 C47 1.392(4) . ? C46 C50 1.395(4) . ? C47 C48 1.383(5) . ? C47 H47 0.9300 . ? C48 H48 0.9300 . ? C49 C50 1.376(5) . ? C49 H49 0.9300 . ? C50 H50 0.9300 . ? N3 C51 1.080(11) . ? N3 C55 1.379(9) . ? N4 C58 1.249(13) . ? N4 C59 1.328(13) . ? C51 C52 1.530(14) . ? C51 H51 0.9300 . ? C52 C53 1.364(10) . ? C52 H52 0.9300 . ? C53 C54 1.392(9) . ? C53 C56 1.483(10) . ? C54 C55 1.336(9) . ? C54 H54 0.9300 . ? C55 H55 0.9300 . ? C56 C60 1.350(11) . ? C56 C57 1.387(11) . ? C57 C58 1.419(15) . ? C57 H57 0.9300 . ? C58 H58 0.9300 . ? C59 C60 1.412(13) . ? C59 H59 0.9300 . ? C60 H60 0.9300 . ? O5 C62 1.222(5) . ? C61 C62 1.472(6) . ? C61 H61A 0.9600 . ? C61 H61B 0.9600 . ? C61 H61C 0.9600 . ? C62 C63 1.453(7) . ? C63 H63A 0.9600 . ? C63 H63B 0.9600 . ? C63 H63C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 O1 H1 109.5 . . ? C10 O2 H2 109.5 . . ? C22 O3 H3 109.5 . . ? C30 O4 H4 109.5 . . ? C41 N1 C45 116.7(3) . . ? C48 N2 C49 116.5(3) . . ? C6 C1 C2 119.4(3) . . ? C6 C1 H1A 120.3 . . ? C2 C1 H1A 120.3 . . ? C3 C2 O1 122.6(3) . . ? C3 C2 C1 120.0(3) . . ? O1 C2 C1 117.3(3) . . ? C2 C3 C4 120.7(3) . . ? C2 C3 H3A 119.6 . . ? C4 C3 H3A 119.6 . . ? C5 C4 C3 120.0(3) . . ? C5 C4 H4A 120.0 . . ? C3 C4 H4A 120.0 . . ? C4 C5 C6 119.6(3) . . ? C4 C5 C14 127.7(3) . . ? C6 C5 C14 112.6(3) . . ? C1 C6 C5 120.3(3) . . ? C1 C6 C7 126.4(3) . . ? C5 C6 C7 113.2(3) . . ? C20 C7 C6 107.1(2) . . ? C20 C7 C8 105.7(3) . . ? C6 C7 C8 105.1(2) . . ? C20 C7 H7 112.8 . . ? C6 C7 H7 112.8 . . ? C8 C7 H7 112.8 . . ? C9 C8 C13 121.0(3) . . ? C9 C8 C7 126.6(3) . . ? C13 C8 C7 112.4(3) . . ? C8 C9 C10 119.5(3) . . ? C8 C9 H9 120.3 . . ? C10 C9 H9 120.3 . . ? O2 C10 C11 118.4(3) . . ? O2 C10 C9 121.3(4) . . ? C11 C10 C9 120.3(3) . . ? C10 C11 C12 120.3(3) . . ? C10 C11 H11 119.8 . . ? C12 C11 H11 119.8 . . ? C11 C12 C13 119.9(3) . . ? C11 C12 H12 120.1 . . ? C13 C12 H12 120.1 . . ? C12 C13 C8 119.0(3) . . ? C12 C13 C14 127.5(3) . . ? C8 C13 C14 113.4(3) . . ? C13 C14 C5 104.3(3) . . ? C13 C14 C15 106.2(3) . . ? C5 C14 C15 106.7(3) . . ? C13 C14 H14 113.0 . . ? C5 C14 H14 113.0 . . ? C15 C14 H14 113.0 . . ? C16 C15 C20 119.7(4) . . ? C16 C15 C14 127.6(3) . . ? C20 C15 C14 112.7(3) . . ? C15 C16 C17 119.6(4) . . ? C15 C16 H16 120.2 . . ? C17 C16 H16 120.2 . . ? C18 C17 C16 121.1(4) . . ? C18 C17 H17 119.5 . . ? C16 C17 H17 119.5 . . ? C17 C18 C19 119.6(4) . . ? C17 C18 H18 120.2 . . ? C19 C18 H18 120.2 . . ? C18 C19 C20 120.2(4) . . ? C18 C19 H19 119.9 . . ? C20 C19 H19 119.9 . . ? C19 C20 C15 119.8(3) . . ? C19 C20 C7 127.1(3) . . ? C15 C20 C7 113.1(3) . . ? C26 C21 C22 118.6(3) . . ? C26 C21 H21 120.7 . . ? C22 C21 H21 120.7 . . ? O3 C22 C23 118.1(3) . . ? O3 C22 C21 121.4(3) . . ? C23 C22 C21 120.5(3) . . ? C22 C23 C24 120.5(3) . . ? C22 C23 H23 119.8 . . ? C24 C23 H23 119.8 . . ? C25 C24 C23 119.7(3) . . ? C25 C24 H24 120.2 . . ? C23 C24 H24 120.2 . . ? C24 C25 C26 119.5(3) . . ? C24 C25 C34 127.7(3) . . ? C26 C25 C34 112.7(2) . . ? C21 C26 C25 121.3(3) . . ? C21 C26 C27 125.6(3) . . ? C25 C26 C27 113.0(3) . . ? C26 C27 C40 105.4(2) . . ? C26 C27 C28 106.1(2) . . ? C40 C27 C28 105.6(2) . . ? C26 C27 H27 113.0 . . ? C40 C27 H27 113.0 . . ? C28 C27 H27 113.0 . . ? C29 C28 C33 121.6(3) . . ? C29 C28 C27 126.3(2) . . ? C33 C28 C27 112.1(3) . . ? C28 C29 C30 119.6(3) . . ? C28 C29 H29 120.2 . . ? C30 C29 H29 120.2 . . ? O4 C30 C31 117.7(3) . . ? O4 C30 C29 123.5(3) . . ? C31 C30 C29 118.8(3) . . ? C32 C31 C30 121.3(3) . . ? C32 C31 H31 119.4 . . ? C30 C31 H31 119.4 . . ? C31 C32 C33 120.0(3) . . ? C31 C32 H32 120.0 . . ? C33 C32 H32 120.0 . . ? C32 C33 C28 118.7(3) . . ? C32 C33 C34 127.3(3) . . ? C28 C33 C34 114.0(3) . . ? C33 C34 C25 106.7(2) . . ? C33 C34 C35 106.1(2) . . ? C25 C34 C35 105.0(2) . . ? C33 C34 H34 112.8 . . ? C25 C34 H34 112.8 . . ? C35 C34 H34 112.8 . . ? C36 C35 C40 119.7(3) . . ? C36 C35 C34 127.9(3) . . ? C40 C35 C34 112.4(3) . . ? C35 C36 C37 119.5(3) . . ? C35 C36 H36 120.3 . . ? C37 C36 H36 120.3 . . ? C38 C37 C36 121.3(3) . . ? C38 C37 H37 119.3 . . ? C36 C37 H37 119.3 . . ? C37 C38 C39 119.9(3) . . ? C37 C38 H38 120.0 . . ? C39 C38 H38 120.0 . . ? C40 C39 C38 119.4(3) . . ? C40 C39 H39 120.3 . . ? C38 C39 H39 120.3 . . ? C39 C40 C35 120.2(3) . . ? C39 C40 C27 126.5(3) . . ? C35 C40 C27 113.2(3) . . ? N1 C41 C42 123.8(3) . . ? N1 C41 H41 118.1 . . ? C42 C41 H41 118.1 . . ? C41 C42 C43 119.9(3) . . ? C41 C42 H42 120.0 . . ? C43 C42 H42 120.0 . . ? C42 C43 C44 116.8(3) . . ? C42 C43 C46 121.9(3) . . ? C44 C43 C46 121.3(3) . . ? C45 C44 C43 119.3(3) . . ? C45 C44 H44 120.4 . . ? C43 C44 H44 120.4 . . ? N1 C45 C44 123.5(3) . . ? N1 C45 H45 118.2 . . ? C44 C45 H45 118.2 . . ? C47 C46 C50 116.0(3) . . ? C47 C46 C43 122.7(3) . . ? C50 C46 C43 121.3(3) . . ? C48 C47 C46 119.8(3) . . ? C48 C47 H47 120.1 . . ? C46 C47 H47 120.1 . . ? N2 C48 C47 123.9(3) . . ? N2 C48 H48 118.0 . . ? C47 C48 H48 118.0 . . ? N2 C49 C50 123.6(3) . . ? N2 C49 H49 118.2 . . ? C50 C49 H49 118.2 . . ? C49 C50 C46 120.2(3) . . ? C49 C50 H50 119.9 . . ? C46 C50 H50 119.9 . . ? C51 N3 C55 116.4(8) . . ? C58 N4 C59 119.6(10) . . ? N3 C51 C52 129.6(8) . . ? N3 C51 H51 115.2 . . ? C52 C51 H51 115.2 . . ? C53 C52 C51 114.3(7) . . ? C53 C52 H52 122.9 . . ? C51 C52 H52 122.9 . . ? C52 C53 C54 114.8(6) . . ? C52 C53 C56 123.4(6) . . ? C54 C53 C56 121.8(6) . . ? C55 C54 C53 122.1(6) . . ? C55 C54 H54 119.0 . . ? C53 C54 H54 119.0 . . ? C54 C55 N3 122.2(7) . . ? C54 C55 H55 118.9 . . ? N3 C55 H55 118.9 . . ? C60 C56 C57 117.0(8) . . ? C60 C56 C53 123.2(6) . . ? C57 C56 C53 119.8(7) . . ? C56 C57 C58 116.3(10) . . ? C56 C57 H57 121.9 . . ? C58 C57 H57 121.9 . . ? N4 C58 C57 125.8(10) . . ? N4 C58 H58 117.1 . . ? C57 C58 H58 117.1 . . ? N4 C59 C60 118.9(11) . . ? N4 C59 H59 120.6 . . ? C60 C59 H59 120.6 . . ? C56 C60 C59 122.3(9) . . ? C56 C60 H60 118.9 . . ? C59 C60 H60 118.9 . . ? C62 C61 H61A 109.5 . . ? C62 C61 H61B 109.5 . . ? H61A C61 H61B 109.5 . . ? C62 C61 H61C 109.5 . . ? H61A C61 H61C 109.5 . . ? H61B C61 H61C 109.5 . . ? O5 C62 C63 122.4(5) . . ? O5 C62 C61 121.2(5) . . ? C63 C62 C61 116.3(5) . . ? C62 C63 H63A 109.5 . . ? C62 C63 H63B 109.5 . . ? H63A C63 H63B 109.5 . . ? C62 C63 H63C 109.5 . . ? H63A C63 H63C 109.5 . . ? H63B C63 H63C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C1 C2 C3 0.1(5) . . . . ? C6 C1 C2 O1 -178.5(3) . . . . ? O1 C2 C3 C4 179.4(3) . . . . ? C1 C2 C3 C4 0.9(5) . . . . ? C2 C3 C4 C5 -1.1(5) . . . . ? C3 C4 C5 C6 0.3(5) . . . . ? C3 C4 C5 C14 -175.3(3) . . . . ? C2 C1 C6 C5 -0.9(5) . . . . ? C2 C1 C6 C7 174.7(3) . . . . ? C4 C5 C6 C1 0.8(5) . . . . ? C14 C5 C6 C1 177.0(3) . . . . ? C4 C5 C6 C7 -175.4(3) . . . . ? C14 C5 C6 C7 0.8(4) . . . . ? C1 C6 C7 C20 128.2(3) . . . . ? C5 C6 C7 C20 -55.9(3) . . . . ? C1 C6 C7 C8 -119.7(3) . . . . ? C5 C6 C7 C8 56.1(3) . . . . ? C20 C7 C8 C9 -125.4(3) . . . . ? C6 C7 C8 C9 121.5(3) . . . . ? C20 C7 C8 C13 57.2(3) . . . . ? C6 C7 C8 C13 -55.8(3) . . . . ? C13 C8 C9 C10 2.6(5) . . . . ? C7 C8 C9 C10 -174.6(3) . . . . ? C8 C9 C10 O2 178.1(3) . . . . ? C8 C9 C10 C11 -1.7(5) . . . . ? O2 C10 C11 C12 -179.7(3) . . . . ? C9 C10 C11 C12 0.1(5) . . . . ? C10 C11 C12 C13 0.7(5) . . . . ? C11 C12 C13 C8 0.1(5) . . . . ? C11 C12 C13 C14 176.4(3) . . . . ? C9 C8 C13 C12 -1.7(5) . . . . ? C7 C8 C13 C12 175.8(3) . . . . ? C9 C8 C13 C14 -178.6(3) . . . . ? C7 C8 C13 C14 -1.0(4) . . . . ? C12 C13 C14 C5 -118.7(4) . . . . ? C8 C13 C14 C5 57.8(3) . . . . ? C12 C13 C14 C15 128.8(4) . . . . ? C8 C13 C14 C15 -54.6(4) . . . . ? C4 C5 C14 C13 118.4(4) . . . . ? C6 C5 C14 C13 -57.5(3) . . . . ? C4 C5 C14 C15 -129.5(4) . . . . ? C6 C5 C14 C15 54.7(3) . . . . ? C13 C14 C15 C16 -123.5(4) . . . . ? C5 C14 C15 C16 125.6(4) . . . . ? C13 C14 C15 C20 54.5(4) . . . . ? C5 C14 C15 C20 -56.3(3) . . . . ? C20 C15 C16 C17 -0.2(5) . . . . ? C14 C15 C16 C17 177.7(3) . . . . ? C15 C16 C17 C18 -0.8(6) . . . . ? C16 C17 C18 C19 1.2(6) . . . . ? C17 C18 C19 C20 -0.7(5) . . . . ? C18 C19 C20 C15 -0.2(5) . . . . ? C18 C19 C20 C7 -179.1(3) . . . . ? C16 C15 C20 C19 0.7(5) . . . . ? C14 C15 C20 C19 -177.5(3) . . . . ? C16 C15 C20 C7 179.7(3) . . . . ? C14 C15 C20 C7 1.5(4) . . . . ? C6 C7 C20 C19 -126.9(3) . . . . ? C8 C7 C20 C19 121.5(3) . . . . ? C6 C7 C20 C15 54.3(3) . . . . ? C8 C7 C20 C15 -57.4(3) . . . . ? C26 C21 C22 O3 179.2(3) . . . . ? C26 C21 C22 C23 -0.3(5) . . . . ? O3 C22 C23 C24 -179.2(3) . . . . ? C21 C22 C23 C24 0.3(5) . . . . ? C22 C23 C24 C25 -0.2(5) . . . . ? C23 C24 C25 C26 0.1(5) . . . . ? C23 C24 C25 C34 177.4(3) . . . . ? C22 C21 C26 C25 0.2(4) . . . . ? C22 C21 C26 C27 -176.4(3) . . . . ? C24 C25 C26 C21 -0.1(5) . . . . ? C34 C25 C26 C21 -177.8(3) . . . . ? C24 C25 C26 C27 176.9(3) . . . . ? C34 C25 C26 C27 -0.8(4) . . . . ? C21 C26 C27 C40 121.3(3) . . . . ? C25 C26 C27 C40 -55.5(3) . . . . ? C21 C26 C27 C28 -127.0(3) . . . . ? C25 C26 C27 C28 56.2(3) . . . . ? C26 C27 C28 C29 126.2(3) . . . . ? C40 C27 C28 C29 -122.2(3) . . . . ? C26 C27 C28 C33 -56.0(3) . . . . ? C40 C27 C28 C33 55.5(3) . . . . ? C33 C28 C29 C30 -0.3(4) . . . . ? C27 C28 C29 C30 177.2(3) . . . . ? C28 C29 C30 O4 179.9(3) . . . . ? C28 C29 C30 C31 0.2(4) . . . . ? O4 C30 C31 C32 -179.6(3) . . . . ? C29 C30 C31 C32 0.0(4) . . . . ? C30 C31 C32 C33 -0.2(5) . . . . ? C31 C32 C33 C28 0.1(4) . . . . ? C31 C32 C33 C34 -177.9(3) . . . . ? C29 C28 C33 C32 0.2(4) . . . . ? C27 C28 C33 C32 -177.7(3) . . . . ? C29 C28 C33 C34 178.4(3) . . . . ? C27 C28 C33 C34 0.6(3) . . . . ? C32 C33 C34 C25 -126.9(3) . . . . ? C28 C33 C34 C25 55.1(3) . . . . ? C32 C33 C34 C35 121.5(3) . . . . ? C28 C33 C34 C35 -56.5(3) . . . . ? C24 C25 C34 C33 127.8(3) . . . . ? C26 C25 C34 C33 -54.7(3) . . . . ? C24 C25 C34 C35 -119.9(3) . . . . ? C26 C25 C34 C35 57.6(3) . . . . ? C33 C34 C35 C36 -125.5(3) . . . . ? C25 C34 C35 C36 121.8(3) . . . . ? C33 C34 C35 C40 55.2(3) . . . . ? C25 C34 C35 C40 -57.6(3) . . . . ? C40 C35 C36 C37 -1.5(5) . . . . ? C34 C35 C36 C37 179.1(3) . . . . ? C35 C36 C37 C38 0.6(6) . . . . ? C36 C37 C38 C39 0.7(6) . . . . ? C37 C38 C39 C40 -1.1(5) . . . . ? C38 C39 C40 C35 0.2(5) . . . . ? C38 C39 C40 C27 179.6(3) . . . . ? C36 C35 C40 C39 1.1(4) . . . . ? C34 C35 C40 C39 -179.4(3) . . . . ? C36 C35 C40 C27 -178.3(3) . . . . ? C34 C35 C40 C27 1.1(4) . . . . ? C26 C27 C40 C39 -123.9(3) . . . . ? C28 C27 C40 C39 124.0(3) . . . . ? C26 C27 C40 C35 55.5(3) . . . . ? C28 C27 C40 C35 -56.6(3) . . . . ? C45 N1 C41 C42 -0.9(5) . . . . ? N1 C41 C42 C43 0.1(5) . . . . ? C41 C42 C43 C44 0.1(4) . . . . ? C41 C42 C43 C46 -179.6(3) . . . . ? C42 C43 C44 C45 0.5(5) . . . . ? C46 C43 C44 C45 -179.8(3) . . . . ? C41 N1 C45 C44 1.6(5) . . . . ? C43 C44 C45 N1 -1.4(5) . . . . ? C42 C43 C46 C47 -147.1(3) . . . . ? C44 C43 C46 C47 33.2(5) . . . . ? C42 C43 C46 C50 32.7(4) . . . . ? C44 C43 C46 C50 -147.0(3) . . . . ? C50 C46 C47 C48 0.5(5) . . . . ? C43 C46 C47 C48 -179.7(3) . . . . ? C49 N2 C48 C47 -0.6(5) . . . . ? C46 C47 C48 N2 0.2(5) . . . . ? C48 N2 C49 C50 0.2(5) . . . . ? N2 C49 C50 C46 0.5(6) . . . . ? C47 C46 C50 C49 -0.8(5) . . . . ? C43 C46 C50 C49 179.4(3) . . . . ? C55 N3 C51 C52 8.5(15) . . . . ? N3 C51 C52 C53 -3.8(16) . . . . ? C51 C52 C53 C54 -2.0(10) . . . . ? C51 C52 C53 C56 179.8(6) . . . . ? C52 C53 C54 C55 2.1(9) . . . . ? C56 C53 C54 C55 -179.7(6) . . . . ? C53 C54 C55 N3 2.5(10) . . . . ? C51 N3 C55 C54 -7.8(11) . . . . ? C52 C53 C56 C60 168.1(7) . . . . ? C54 C53 C56 C60 -10.0(9) . . . . ? C52 C53 C56 C57 -9.7(9) . . . . ? C54 C53 C56 C57 172.3(6) . . . . ? C60 C56 C57 C58 3.6(11) . . . . ? C53 C56 C57 C58 -178.5(7) . . . . ? C59 N4 C58 C57 -0.7(16) . . . . ? C56 C57 C58 N4 -2.8(15) . . . . ? C58 N4 C59 C60 3.1(14) . . . . ? C57 C56 C60 C59 -1.4(12) . . . . ? C53 C56 C60 C59 -179.2(7) . . . . ? N4 C59 C60 C56 -2.1(13) . . . . ? _diffrn_measured_fraction_theta_max 0.987 _diffrn_reflns_theta_full 25.02 _diffrn_measured_fraction_theta_full 0.987 _refine_diff_density_max 0.471 _refine_diff_density_min -0.293 _refine_diff_density_rms 0.059 # Attachment '2a.cif' data_2a _database_code_depnum_ccdc_archive 'CCDC 760762' #TrackingRef '2a.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C26 H26 O5' _chemical_formula_sum 'C26 H26 O5' _chemical_formula_weight 418.47 _chemical_absolute_configuration unk 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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 21 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 10.7093(7) _cell_length_b 8.1477(4) _cell_length_c 12.8858(8) _cell_angle_alpha 90.00 _cell_angle_beta 102.935(3) _cell_angle_gamma 90.00 _cell_volume 1095.83(11) _cell_formula_units_Z 2 _cell_measurement_temperature 113(2) _cell_measurement_reflns_used 3666 _cell_measurement_theta_min 1.6 _cell_measurement_theta_max 28.7 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.268 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 444 _exptl_absorpt_coefficient_mu 0.087 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9726 _exptl_absorpt_correction_T_max 0.9828 _exptl_absorpt_process_details 'Jacobson, R. (1998) Private communication' _exptl_special_details ; ? ; _diffrn_ambient_temperature 113(2) _diffrn_radiation_wavelength 0.71070 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating anode' _diffrn_radiation_monochromator confocal _diffrn_measurement_device_type 'Rigaku Saturn' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 7.31 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 14503 _diffrn_reflns_av_R_equivalents 0.0462 _diffrn_reflns_av_sigmaI/netI 0.0632 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.62 _diffrn_reflns_theta_max 28.67 _reflns_number_total 3010 _reflns_number_gt 2588 _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 ? _computing_publication_material 'CrystalStructure 3.7.0' _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^)+(0.0521P)^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 mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.041(5) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'None, Friedel Pairs merged' _refine_ls_abs_structure_Flack ? _refine_ls_number_reflns 3010 _refine_ls_number_parameters 294 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0450 _refine_ls_R_factor_gt 0.0380 _refine_ls_wR_factor_ref 0.0864 _refine_ls_wR_factor_gt 0.0830 _refine_ls_goodness_of_fit_ref 0.999 _refine_ls_restrained_S_all 0.998 _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 O1 O 0.90155(13) 0.4148(2) 0.49130(12) 0.0261(3) Uani 1 1 d . . . O2 O 0.62668(15) 1.0350(2) 0.02074(11) 0.0267(3) Uani 1 1 d . . . O3 O 0.08664(14) 0.2925(2) 0.18769(12) 0.0282(4) Uani 1 1 d . . . O4 O 0.92466(13) 1.20249(18) 0.32240(11) 0.0252(3) Uani 1 1 d . . . O5 O 0.72193(16) 0.3457(2) 0.07439(13) 0.0389(4) Uani 1 1 d . . . C1 C 0.50313(17) 0.5823(2) 0.23058(14) 0.0162(4) Uani 1 1 d . . . H1 H 0.5262 0.5045 0.1778 0.019 Uiso 1 1 calc R . . C2 C 0.59570(18) 0.5757(2) 0.33921(14) 0.0170(4) Uani 1 1 d . . . C3 C 0.70690(18) 0.4835(2) 0.36352(15) 0.0183(4) Uani 1 1 d . . . H3 H 0.7273 0.4092 0.3129 0.022 Uiso 1 1 calc R . . C4 C 0.78862(17) 0.5014(3) 0.46361(15) 0.0196(4) Uani 1 1 d . . . C5 C 0.75853(19) 0.6096(2) 0.53737(15) 0.0204(4) Uani 1 1 d . . . H5 H 0.8145 0.6204 0.6055 0.025 Uiso 1 1 calc R . . C6 C 0.64613(18) 0.7029(3) 0.51207(15) 0.0194(4) Uani 1 1 d . . . H6 H 0.6260 0.7777 0.5625 0.023 Uiso 1 1 calc R . . C7 C 0.56455(17) 0.6855(2) 0.41308(14) 0.0173(4) Uani 1 1 d . . . C8 C 0.44371(17) 0.7856(2) 0.36752(14) 0.0173(4) Uani 1 1 d . . . H8 H 0.4207 0.8635 0.4202 0.021 Uiso 1 1 calc R . . C9 C 0.33834(18) 0.6615(2) 0.32447(15) 0.0180(4) Uani 1 1 d . . . C10 C 0.22015(19) 0.6490(3) 0.35091(15) 0.0217(4) Uani 1 1 d . . . H10 H 0.1971 0.7243 0.3998 0.026 Uiso 1 1 calc R . . C11 C 0.13509(18) 0.5254(3) 0.30549(15) 0.0233(4) Uani 1 1 d . . . H11 H 0.0543 0.5161 0.3239 0.028 Uiso 1 1 calc R . . C12 C 0.16797(18) 0.4166(3) 0.23376(15) 0.0202(4) Uani 1 1 d . . . C13 C 0.28606(18) 0.4298(2) 0.20488(15) 0.0187(4) Uani 1 1 d . . . H13 H 0.3080 0.3560 0.1547 0.022 Uiso 1 1 calc R . . C14 C 0.37004(17) 0.5517(2) 0.25056(14) 0.0168(4) Uani 1 1 d . . . C15 C 0.50898(17) 0.7620(2) 0.19854(14) 0.0167(4) Uani 1 1 d . . . C16 C 0.55682(17) 0.8180(3) 0.11390(14) 0.0180(4) Uani 1 1 d . . . H16 H 0.5798 0.7427 0.0651 0.022 Uiso 1 1 calc R . . C17 C 0.57089(18) 0.9863(3) 0.10112(15) 0.0195(4) Uani 1 1 d . . . C18 C 0.53006(19) 1.0962(2) 0.16888(15) 0.0217(4) Uani 1 1 d . . . H18 H 0.5349 1.2110 0.1572 0.026 Uiso 1 1 calc R . . C19 C 0.48192(18) 1.0386(3) 0.25427(15) 0.0206(4) Uani 1 1 d . . . H19 H 0.4545 1.1139 0.3009 0.025 Uiso 1 1 calc R . . C20 C 0.47430(18) 0.8714(2) 0.27084(14) 0.0177(4) Uani 1 1 d . . . C21 C 0.8066(2) 0.9896(3) 0.38137(18) 0.0350(6) Uani 1 1 d . . . H21A H 0.7902 1.0739 0.4309 0.042 Uiso 1 1 calc R . . H21B H 0.8508 0.8964 0.4217 0.042 Uiso 1 1 calc R . . H21C H 0.7251 0.9524 0.3367 0.042 Uiso 1 1 calc R . . C22 C 0.88756(18) 1.0590(3) 0.31324(16) 0.0239(4) Uani 1 1 d . . . C23 C 0.9227(2) 0.9492(3) 0.2323(2) 0.0398(6) Uani 1 1 d . . . H23A H 0.9760 1.0096 0.1925 0.048 Uiso 1 1 calc R . . H23B H 0.8447 0.9108 0.1831 0.048 Uiso 1 1 calc R . . H23C H 0.9707 0.8547 0.2678 0.048 Uiso 1 1 calc R . . C24 C 0.8474(2) 0.5794(3) 0.0660(3) 0.0497(7) Uani 1 1 d . . . H24A H 0.8115 0.6153 0.1258 0.060 Uiso 1 1 calc R . . H24B H 0.8233 0.6576 0.0071 0.060 Uiso 1 1 calc R . . H24C H 0.9410 0.5742 0.0886 0.060 Uiso 1 1 calc R . . C25 C 0.7964(2) 0.4139(3) 0.03009(17) 0.0282(5) Uani 1 1 d . . . C26 C 0.8396(3) 0.3377(4) -0.0598(2) 0.0513(8) Uani 1 1 d . . . H26A H 0.7990 0.2300 -0.0753 0.062 Uiso 1 1 calc R . . H26B H 0.9329 0.3246 -0.0411 0.062 Uiso 1 1 calc R . . H26C H 0.8155 0.4081 -0.1228 0.062 Uiso 1 1 calc R . . H2 H 0.909(3) 0.347(4) 0.443(2) 0.048(9) Uiso 1 1 d . . . H4 H 0.027(3) 0.278(4) 0.232(2) 0.052(8) Uiso 1 1 d . . . H7 H 0.645(3) 1.143(4) 0.025(2) 0.050(9) 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 O1 0.0202(7) 0.0285(8) 0.0275(8) 0.0014(7) 0.0006(6) 0.0040(7) O2 0.0328(8) 0.0267(9) 0.0232(7) 0.0044(7) 0.0117(6) -0.0016(7) O3 0.0248(8) 0.0303(9) 0.0298(8) -0.0046(7) 0.0069(6) -0.0112(7) O4 0.0213(7) 0.0234(8) 0.0319(8) -0.0003(7) 0.0083(6) -0.0009(6) O5 0.0394(9) 0.0404(10) 0.0411(9) -0.0067(8) 0.0182(7) -0.0137(8) C1 0.0178(9) 0.0143(9) 0.0172(9) -0.0019(7) 0.0056(7) 0.0011(7) C2 0.0185(9) 0.0153(9) 0.0177(9) 0.0022(8) 0.0054(7) -0.0033(8) C3 0.0191(9) 0.0169(9) 0.0200(9) 0.0001(8) 0.0066(7) -0.0020(8) C4 0.0157(9) 0.0205(10) 0.0222(10) 0.0047(8) 0.0034(7) -0.0012(8) C5 0.0207(10) 0.0219(11) 0.0172(9) 0.0027(8) 0.0009(7) -0.0063(8) C6 0.0238(10) 0.0177(10) 0.0181(9) -0.0005(8) 0.0079(7) -0.0065(8) C7 0.0202(9) 0.0156(9) 0.0173(9) 0.0013(8) 0.0070(7) -0.0027(8) C8 0.0202(9) 0.0160(10) 0.0171(9) -0.0026(8) 0.0073(7) 0.0006(8) C9 0.0203(10) 0.0163(10) 0.0180(9) 0.0010(8) 0.0054(7) 0.0016(8) C10 0.0250(11) 0.0221(10) 0.0199(10) 0.0007(8) 0.0090(8) 0.0018(9) C11 0.0190(9) 0.0267(11) 0.0259(10) 0.0021(9) 0.0086(8) -0.0002(9) C12 0.0192(9) 0.0194(9) 0.0208(10) 0.0036(8) 0.0015(7) -0.0029(8) C13 0.0208(9) 0.0180(10) 0.0168(9) 0.0010(8) 0.0033(7) 0.0009(8) C14 0.0177(9) 0.0162(9) 0.0162(8) 0.0036(8) 0.0032(7) 0.0017(8) C15 0.0138(9) 0.0181(9) 0.0166(9) -0.0003(8) 0.0000(7) -0.0001(7) C16 0.0165(9) 0.0202(10) 0.0173(9) -0.0024(8) 0.0034(7) 0.0021(8) C17 0.0189(9) 0.0231(10) 0.0167(9) 0.0037(8) 0.0041(7) -0.0027(8) C18 0.0254(10) 0.0143(10) 0.0258(10) 0.0039(8) 0.0067(8) 0.0017(8) C19 0.0212(10) 0.0172(10) 0.0241(10) -0.0014(8) 0.0063(8) 0.0019(8) C20 0.0158(9) 0.0198(10) 0.0175(9) -0.0009(8) 0.0039(7) 0.0010(8) C21 0.0295(12) 0.0403(14) 0.0334(12) 0.0088(11) 0.0031(9) -0.0097(11) C22 0.0160(9) 0.0238(11) 0.0302(11) 0.0018(9) 0.0017(8) -0.0002(9) C23 0.0385(13) 0.0318(14) 0.0516(15) -0.0134(11) 0.0156(11) -0.0057(11) C24 0.0343(14) 0.0282(13) 0.081(2) 0.0006(14) -0.0001(13) -0.0029(12) C25 0.0232(11) 0.0269(11) 0.0320(11) 0.0042(10) 0.0010(9) -0.0009(10) C26 0.0401(15) 0.075(2) 0.0420(14) -0.0161(15) 0.0158(12) -0.0142(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 C4 1.377(2) . ? O1 H2 0.85(3) . ? O2 C17 1.365(2) . ? O2 H7 0.90(3) . ? O3 C12 1.379(2) . ? O3 H4 0.96(3) . ? O4 C22 1.232(3) . ? O5 C25 1.215(3) . ? C1 C2 1.524(2) . ? C1 C14 1.525(2) . ? C1 C15 1.526(3) . ? C1 H1 1.0000 . ? C2 C3 1.383(3) . ? C2 C7 1.400(3) . ? C3 C4 1.395(3) . ? C3 H3 0.9500 . ? C4 C5 1.386(3) . ? C5 C6 1.399(3) . ? C5 H5 0.9500 . ? C6 C7 1.383(3) . ? C6 H6 0.9500 . ? C7 C8 1.531(3) . ? C8 C9 1.524(3) . ? C8 C20 1.527(3) . ? C8 H8 1.0000 . ? C9 C10 1.386(3) . ? C9 C14 1.403(3) . ? C10 C11 1.395(3) . ? C10 H10 0.9500 . ? C11 C12 1.382(3) . ? C11 H11 0.9500 . ? C12 C13 1.400(3) . ? C13 C14 1.380(3) . ? C13 H13 0.9500 . ? C15 C16 1.382(3) . ? C15 C20 1.398(3) . ? C16 C17 1.394(3) . ? C16 H16 0.9500 . ? C17 C18 1.388(3) . ? C18 C19 1.397(3) . ? C18 H18 0.9500 . ? C19 C20 1.384(3) . ? C19 H19 0.9500 . ? C21 C22 1.477(3) . ? C21 H21A 0.9800 . ? C21 H21B 0.9800 . ? C21 H21C 0.9800 . ? C22 C23 1.486(3) . ? C23 H23A 0.9800 . ? C23 H23B 0.9800 . ? C23 H23C 0.9800 . ? C24 C25 1.489(4) . ? C24 H24A 0.9800 . ? C24 H24B 0.9800 . ? C24 H24C 0.9800 . ? C25 C26 1.477(3) . ? C26 H26A 0.9800 . ? C26 H26B 0.9800 . ? C26 H26C 0.9800 . ? 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 C4 O1 H2 111.2(19) . . ? C17 O2 H7 111.7(17) . . ? C12 O3 H4 105.8(18) . . ? C2 C1 C14 106.23(14) . . ? C2 C1 C15 102.99(15) . . ? C14 C1 C15 107.40(16) . . ? C2 C1 H1 113.2 . . ? C14 C1 H1 113.2 . . ? C15 C1 H1 113.2 . . ? C3 C2 C7 121.15(17) . . ? C3 C2 C1 125.24(17) . . ? C7 C2 C1 113.37(16) . . ? C2 C3 C4 118.85(18) . . ? C2 C3 H3 120.6 . . ? C4 C3 H3 120.6 . . ? O1 C4 C5 118.30(17) . . ? O1 C4 C3 121.25(18) . . ? C5 C4 C3 120.45(17) . . ? C4 C5 C6 120.39(17) . . ? C4 C5 H5 119.8 . . ? C6 C5 H5 119.8 . . ? C7 C6 C5 119.48(18) . . ? C7 C6 H6 120.3 . . ? C5 C6 H6 120.3 . . ? C6 C7 C2 119.69(18) . . ? C6 C7 C8 127.19(17) . . ? C2 C7 C8 112.91(15) . . ? C9 C8 C20 106.47(14) . . ? C9 C8 C7 106.25(16) . . ? C20 C8 C7 103.85(15) . . ? C9 C8 H8 113.2 . . ? C20 C8 H8 113.2 . . ? C7 C8 H8 113.2 . . ? C10 C9 C14 119.54(18) . . ? C10 C9 C8 126.99(17) . . ? C14 C9 C8 113.46(16) . . ? C9 C10 C11 119.75(18) . . ? C9 C10 H10 120.1 . . ? C11 C10 H10 120.1 . . ? C12 C11 C10 120.21(18) . . ? C12 C11 H11 119.9 . . ? C10 C11 H11 119.9 . . ? O3 C12 C11 121.83(18) . . ? O3 C12 C13 117.56(18) . . ? C11 C12 C13 120.61(18) . . ? C14 C13 C12 118.88(18) . . ? C14 C13 H13 120.6 . . ? C12 C13 H13 120.6 . . ? C13 C14 C9 120.99(17) . . ? C13 C14 C1 126.17(17) . . ? C9 C14 C1 112.82(16) . . ? C16 C15 C20 121.07(18) . . ? C16 C15 C1 125.09(17) . . ? C20 C15 C1 113.46(16) . . ? C15 C16 C17 119.14(18) . . ? C15 C16 H16 120.4 . . ? C17 C16 H16 120.4 . . ? O2 C17 C18 122.86(19) . . ? O2 C17 C16 116.93(18) . . ? C18 C17 C16 120.20(18) . . ? C17 C18 C19 120.15(18) . . ? C17 C18 H18 119.9 . . ? C19 C18 H18 119.9 . . ? C20 C19 C18 119.83(18) . . ? C20 C19 H19 120.1 . . ? C18 C19 H19 120.1 . . ? C19 C20 C15 119.40(17) . . ? C19 C20 C8 127.41(17) . . ? C15 C20 C8 112.90(17) . . ? C22 C21 H21A 109.5 . . ? C22 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C22 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? O4 C22 C21 121.7(2) . . ? O4 C22 C23 120.8(2) . . ? C21 C22 C23 117.5(2) . . ? C22 C23 H23A 109.5 . . ? C22 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C22 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? C25 C24 H24A 109.5 . . ? C25 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C25 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? O5 C25 C26 122.0(2) . . ? O5 C25 C24 120.1(2) . . ? C26 C25 C24 117.8(2) . . ? C25 C26 H26A 109.5 . . ? C25 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? C25 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C14 C1 C2 C3 129.78(19) . . . . ? C15 C1 C2 C3 -117.5(2) . . . . ? C14 C1 C2 C7 -55.8(2) . . . . ? C15 C1 C2 C7 56.93(19) . . . . ? C7 C2 C3 C4 0.0(3) . . . . ? C1 C2 C3 C4 173.98(18) . . . . ? C2 C3 C4 O1 -178.90(17) . . . . ? C2 C3 C4 C5 0.2(3) . . . . ? O1 C4 C5 C6 178.66(18) . . . . ? C3 C4 C5 C6 -0.4(3) . . . . ? C4 C5 C6 C7 0.5(3) . . . . ? C5 C6 C7 C2 -0.4(3) . . . . ? C5 C6 C7 C8 -174.71(18) . . . . ? C3 C2 C7 C6 0.1(3) . . . . ? C1 C2 C7 C6 -174.51(17) . . . . ? C3 C2 C7 C8 175.22(18) . . . . ? C1 C2 C7 C8 0.6(2) . . . . ? C6 C7 C8 C9 -130.6(2) . . . . ? C2 C7 C8 C9 54.7(2) . . . . ? C6 C7 C8 C20 117.3(2) . . . . ? C2 C7 C8 C20 -57.4(2) . . . . ? C20 C8 C9 C10 -124.9(2) . . . . ? C7 C8 C9 C10 124.9(2) . . . . ? C20 C8 C9 C14 55.1(2) . . . . ? C7 C8 C9 C14 -55.2(2) . . . . ? C14 C9 C10 C11 1.3(3) . . . . ? C8 C9 C10 C11 -178.71(18) . . . . ? C9 C10 C11 C12 -0.5(3) . . . . ? C10 C11 C12 O3 179.67(18) . . . . ? C10 C11 C12 C13 -0.7(3) . . . . ? O3 C12 C13 C14 -179.30(16) . . . . ? C11 C12 C13 C14 1.0(3) . . . . ? C12 C13 C14 C9 -0.2(3) . . . . ? C12 C13 C14 C1 178.68(17) . . . . ? C10 C9 C14 C13 -1.0(3) . . . . ? C8 C9 C14 C13 179.06(17) . . . . ? C10 C9 C14 C1 -179.98(16) . . . . ? C8 C9 C14 C1 0.0(2) . . . . ? C2 C1 C14 C13 -123.59(19) . . . . ? C15 C1 C14 C13 126.75(19) . . . . ? C2 C1 C14 C9 55.4(2) . . . . ? C15 C1 C14 C9 -54.29(19) . . . . ? C2 C1 C15 C16 114.24(19) . . . . ? C14 C1 C15 C16 -133.86(18) . . . . ? C2 C1 C15 C20 -58.76(19) . . . . ? C14 C1 C15 C20 53.14(19) . . . . ? C20 C15 C16 C17 0.2(3) . . . . ? C1 C15 C16 C17 -172.27(18) . . . . ? C15 C16 C17 O2 175.62(16) . . . . ? C15 C16 C17 C18 -3.9(3) . . . . ? O2 C17 C18 C19 -175.49(18) . . . . ? C16 C17 C18 C19 4.0(3) . . . . ? C17 C18 C19 C20 -0.4(3) . . . . ? C18 C19 C20 C15 -3.2(3) . . . . ? C18 C19 C20 C8 170.21(17) . . . . ? C16 C15 C20 C19 3.3(3) . . . . ? C1 C15 C20 C19 176.62(18) . . . . ? C16 C15 C20 C8 -171.02(16) . . . . ? C1 C15 C20 C8 2.3(2) . . . . ? C9 C8 C20 C19 129.9(2) . . . . ? C7 C8 C20 C19 -118.1(2) . . . . ? C9 C8 C20 C15 -56.3(2) . . . . ? C7 C8 C20 C15 55.6(2) . . . . ? 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 O2 H7 O5 0.90(3) 1.89(3) 2.758(2) 161(3) 1_565 O3 H4 O4 0.96(3) 1.87(3) 2.812(2) 167(3) 1_445 O1 H2 O4 0.85(3) 1.98(3) 2.834(2) 176(3) 1_545 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 28.67 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.205 _refine_diff_density_min -0.179 _refine_diff_density_rms 0.041 # Attachment '2b.cif' data_60518d _database_code_depnum_ccdc_archive 'CCDC 760763' #TrackingRef '2b.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C31.50 H25 N2 O3.50' _chemical_formula_weight 487.54 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 C2/c 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' '-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 21.878(11) _cell_length_b 8.005(4) _cell_length_c 29.006(14) _cell_angle_alpha 90.00 _cell_angle_beta 92.085(8) _cell_angle_gamma 90.00 _cell_volume 5076(4) _cell_formula_units_Z 8 _cell_measurement_temperature 294(2) _cell_measurement_reflns_used 3553 _cell_measurement_theta_min 2.37 _cell_measurement_theta_max 24.66 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 1.276 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2048 _exptl_absorpt_coefficient_mu 0.084 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.783296 _exptl_absorpt_correction_T_max 1.000000 _exptl_absorpt_process_details sadabs _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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number . _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% . _diffrn_reflns_number 12492 _diffrn_reflns_av_R_equivalents 0.0478 _diffrn_reflns_av_sigmaI/netI 0.0523 _diffrn_reflns_limit_h_min -26 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -34 _diffrn_reflns_limit_l_max 34 _diffrn_reflns_theta_min 1.40 _diffrn_reflns_theta_max 25.02 _reflns_number_total 4485 _reflns_number_gt 2703 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1021P)^2^+0.2777P] 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 4485 _refine_ls_number_parameters 339 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0953 _refine_ls_R_factor_gt 0.0510 _refine_ls_wR_factor_ref 0.1830 _refine_ls_wR_factor_gt 0.1453 _refine_ls_goodness_of_fit_ref 1.058 _refine_ls_restrained_S_all 1.058 _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 0.48382(13) 0.5526(3) 0.41604(10) 0.0870(8) Uani 1 1 d . . . H1 H 0.5042 0.6330 0.4250 0.131 Uiso 1 1 calc R . . O2 O 0.43223(11) 1.1750(3) 0.18131(7) 0.0658(6) Uani 1 1 d . . . H2 H 0.4539 1.2379 0.1972 0.099 Uiso 1 1 calc R . . O3 O 0.19266(11) 1.2727(2) 0.41993(8) 0.0632(6) Uani 1 1 d . . . H3 H 0.2187 1.3445 0.4253 0.095 Uiso 1 1 calc R . . C1 C 0.37852(13) 0.8236(3) 0.34989(9) 0.0411(7) Uani 1 1 d . . . C2 C 0.42698(14) 0.7754(3) 0.37858(10) 0.0485(7) Uani 1 1 d . . . H2A H 0.4529 0.8552 0.3920 0.058 Uiso 1 1 calc R . . C3 C 0.43676(15) 0.6063(3) 0.38729(11) 0.0569(8) Uani 1 1 d . . . C4 C 0.39894(16) 0.4895(4) 0.36647(12) 0.0645(9) Uani 1 1 d . . . H4 H 0.4061 0.3764 0.3716 0.077 Uiso 1 1 calc R . . C5 C 0.35027(15) 0.5392(3) 0.33792(11) 0.0563(8) Uani 1 1 d . . . H5 H 0.3248 0.4590 0.3242 0.068 Uiso 1 1 calc R . . C6 C 0.33905(13) 0.7055(3) 0.32966(9) 0.0440(7) Uani 1 1 d . . . C7 C 0.28822(13) 0.7862(3) 0.29971(9) 0.0452(7) Uani 1 1 d . . . H7 H 0.2597 0.7045 0.2859 0.054 Uiso 1 1 calc R . . C8 C 0.32142(13) 0.8884(3) 0.26382(9) 0.0441(7) Uani 1 1 d . . . C9 C 0.31745(14) 0.8729(3) 0.21645(10) 0.0502(7) Uani 1 1 d . . . H9 H 0.2902 0.7970 0.2028 0.060 Uiso 1 1 calc R . . C10 C 0.35435(14) 0.9710(4) 0.18908(10) 0.0528(8) Uani 1 1 d . . . H10 H 0.3514 0.9612 0.1571 0.063 Uiso 1 1 calc R . . C11 C 0.39538(14) 1.0832(3) 0.20943(10) 0.0487(7) Uani 1 1 d . . . C12 C 0.39899(14) 1.1022(3) 0.25724(10) 0.0461(7) Uani 1 1 d . . . H12 H 0.4257 1.1796 0.2708 0.055 Uiso 1 1 calc R . . C13 C 0.36245(12) 1.0047(3) 0.28402(9) 0.0408(6) Uani 1 1 d . . . C14 C 0.36301(12) 1.0025(3) 0.33650(9) 0.0413(6) Uani 1 1 d . . . H14 H 0.3915 1.0841 0.3505 0.050 Uiso 1 1 calc R . . C15 C 0.29722(13) 1.0291(3) 0.35034(9) 0.0398(6) Uani 1 1 d . . . C16 C 0.27721(13) 1.1503(3) 0.38014(9) 0.0408(6) Uani 1 1 d . . . H16 H 0.3046 1.2278 0.3930 0.049 Uiso 1 1 calc R . . C17 C 0.21531(14) 1.1554(3) 0.39074(9) 0.0470(7) Uani 1 1 d . . . C18 C 0.17542(14) 1.0392(3) 0.37157(10) 0.0525(8) Uani 1 1 d . . . H18 H 0.1343 1.0421 0.3787 0.063 Uiso 1 1 calc R . . C19 C 0.19619(14) 0.9181(3) 0.34177(10) 0.0508(7) Uani 1 1 d . . . H19 H 0.1689 0.8405 0.3290 0.061 Uiso 1 1 calc R . . C20 C 0.25705(13) 0.9120(3) 0.33098(9) 0.0438(7) Uani 1 1 d . . . N1 N 0.22485(14) -0.0028(3) 0.04514(9) 0.0629(7) Uani 1 1 d . . . N2 N 0.04700(13) 0.6702(4) -0.04625(10) 0.0665(8) Uani 1 1 d . . . C21 C 0.23019(16) 0.1522(4) 0.06144(10) 0.0587(8) Uani 1 1 d . . . H21 H 0.2589 0.1722 0.0852 0.070 Uiso 1 1 calc R . . C22 C 0.19582(15) 0.2839(4) 0.04516(10) 0.0549(8) Uani 1 1 d . . . H22 H 0.2021 0.3901 0.0575 0.066 Uiso 1 1 calc R . . C23 C 0.15137(15) 0.2589(3) 0.01000(10) 0.0527(8) Uani 1 1 d . . . C24 C 0.14543(17) 0.0973(4) -0.00655(11) 0.0658(9) Uani 1 1 d . . . H24 H 0.1165 0.0729 -0.0299 0.079 Uiso 1 1 calc R . . C25 C 0.18217(18) -0.0264(4) 0.01149(12) 0.0698(10) Uani 1 1 d . . . H25 H 0.1772 -0.1337 -0.0004 0.084 Uiso 1 1 calc R . . C26 C 0.11462(14) 0.3999(4) -0.00915(10) 0.0534(8) Uani 1 1 d . . . C27 C 0.09572(16) 0.4054(4) -0.05574(11) 0.0633(9) Uani 1 1 d . . . H27 H 0.1049 0.3178 -0.0754 0.076 Uiso 1 1 calc R . . C28 C 0.06369(16) 0.5409(5) -0.07216(12) 0.0720(10) Uani 1 1 d . . . H28 H 0.0528 0.5434 -0.1034 0.086 Uiso 1 1 calc R . . C29 C 0.06457(16) 0.6632(4) -0.00137(13) 0.0649(9) Uani 1 1 d . . . H29 H 0.0534 0.7506 0.0177 0.078 Uiso 1 1 calc R . . C30 C 0.09805(15) 0.5341(4) 0.01778(11) 0.0601(8) Uani 1 1 d . . . H30 H 0.1096 0.5367 0.0489 0.072 Uiso 1 1 calc R . . O4 O 0.5000 0.3964(4) 0.2500 0.0720(9) Uani 1 2 d S . . C31 C 0.5000 0.5472(5) 0.2500 0.0604(12) Uani 1 2 d S . . C32 C 0.4625(3) 0.6433(5) 0.21576(19) 0.1275(19) Uani 1 1 d . . . H32A H 0.4439 0.5680 0.1936 0.191 Uiso 1 1 calc R . . H32B H 0.4880 0.7210 0.2002 0.191 Uiso 1 1 calc R . . H32C H 0.4312 0.7032 0.2312 0.191 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 0.083(2) 0.0579(14) 0.118(2) 0.0040(14) -0.0294(16) 0.0174(13) O2 0.0665(17) 0.0674(15) 0.0647(14) 0.0131(11) 0.0185(12) 0.0000(11) O3 0.0657(16) 0.0560(13) 0.0691(14) -0.0049(10) 0.0173(12) 0.0109(10) C1 0.0457(18) 0.0348(13) 0.0429(15) -0.0046(11) 0.0050(13) -0.0042(12) C2 0.0502(19) 0.0403(15) 0.0550(18) -0.0066(12) 0.0007(15) -0.0008(12) C3 0.056(2) 0.0466(16) 0.068(2) 0.0019(15) -0.0052(16) 0.0064(15) C4 0.076(2) 0.0354(15) 0.081(2) 0.0018(15) 0.001(2) 0.0022(15) C5 0.068(2) 0.0354(15) 0.066(2) -0.0050(13) 0.0054(17) -0.0106(14) C6 0.0487(18) 0.0356(14) 0.0480(16) -0.0043(11) 0.0055(13) -0.0071(12) C7 0.0485(18) 0.0364(13) 0.0505(16) -0.0072(12) 0.0002(14) -0.0138(12) C8 0.0495(18) 0.0355(13) 0.0474(17) -0.0051(11) 0.0015(13) -0.0045(12) C9 0.057(2) 0.0421(15) 0.0509(18) -0.0095(13) -0.0007(15) 0.0006(13) C10 0.062(2) 0.0542(17) 0.0426(17) -0.0022(13) 0.0029(15) 0.0099(15) C11 0.0543(19) 0.0393(15) 0.0536(18) 0.0088(13) 0.0151(15) 0.0081(13) C12 0.0511(18) 0.0341(13) 0.0534(18) -0.0005(12) 0.0058(14) -0.0009(12) C13 0.0469(17) 0.0307(13) 0.0448(16) -0.0027(11) 0.0027(13) -0.0016(11) C14 0.0439(17) 0.0320(13) 0.0480(16) -0.0076(11) 0.0007(12) -0.0086(11) C15 0.0469(17) 0.0326(13) 0.0398(14) 0.0021(11) 0.0027(12) -0.0026(11) C16 0.0472(18) 0.0327(13) 0.0424(15) 0.0051(11) -0.0011(13) -0.0047(11) C17 0.055(2) 0.0416(15) 0.0449(16) 0.0110(12) 0.0061(14) 0.0063(13) C18 0.0451(18) 0.0528(17) 0.0600(19) 0.0110(14) 0.0079(15) -0.0011(14) C19 0.0450(19) 0.0462(16) 0.0608(19) 0.0040(13) -0.0035(15) -0.0116(13) C20 0.0493(18) 0.0381(14) 0.0439(16) 0.0013(11) -0.0005(13) -0.0082(12) N1 0.077(2) 0.0571(16) 0.0560(16) 0.0021(13) 0.0150(15) -0.0082(14) N2 0.0464(17) 0.086(2) 0.0675(19) 0.0114(15) 0.0028(14) -0.0047(14) C21 0.071(2) 0.0604(19) 0.0451(17) -0.0044(14) 0.0084(16) -0.0083(17) C22 0.065(2) 0.0519(17) 0.0486(18) -0.0092(14) 0.0065(16) -0.0080(15) C23 0.063(2) 0.0524(17) 0.0436(16) -0.0032(13) 0.0117(15) -0.0135(15) C24 0.080(3) 0.059(2) 0.058(2) -0.0092(16) 0.0057(18) -0.0201(18) C25 0.090(3) 0.0479(18) 0.073(2) -0.0083(16) 0.017(2) -0.0189(18) C26 0.054(2) 0.0588(18) 0.0482(18) 0.0012(14) 0.0081(15) -0.0133(14) C27 0.051(2) 0.088(2) 0.0513(19) -0.0029(16) 0.0059(16) -0.0005(17) C28 0.054(2) 0.105(3) 0.057(2) 0.005(2) 0.0036(17) 0.000(2) C29 0.058(2) 0.062(2) 0.075(2) -0.0022(17) 0.0070(18) -0.0112(16) C30 0.068(2) 0.0588(19) 0.0536(19) -0.0004(15) 0.0003(16) -0.0114(16) O4 0.061(2) 0.0448(17) 0.111(3) 0.000 0.0138(19) 0.000 C31 0.047(3) 0.044(2) 0.092(3) 0.000 0.016(2) 0.000 C32 0.138(5) 0.091(3) 0.151(5) 0.025(3) -0.023(4) 0.034(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C3 1.370(4) . ? O1 H1 0.8200 . ? O2 C11 1.379(3) . ? O2 H2 0.8200 . ? O3 C17 1.369(3) . ? O3 H3 0.8200 . ? C1 C2 1.379(4) . ? C1 C6 1.395(4) . ? C1 C14 1.519(3) . ? C2 C3 1.392(4) . ? C2 H2A 0.9300 . ? C3 C4 1.373(4) . ? C4 C5 1.383(4) . ? C4 H4 0.9300 . ? C5 C6 1.373(4) . ? C5 H5 0.9300 . ? C6 C7 1.529(4) . ? C7 C8 1.528(4) . ? C7 C20 1.532(4) . ? C7 H7 0.9800 . ? C8 C9 1.379(4) . ? C8 C13 1.406(4) . ? C9 C10 1.395(4) . ? C9 H9 0.9300 . ? C10 C11 1.386(4) . ? C10 H10 0.9300 . ? C11 C12 1.394(4) . ? C12 C13 1.377(4) . ? C12 H12 0.9300 . ? C13 C14 1.522(4) . ? C14 C15 1.523(4) . ? C14 H14 0.9800 . ? C15 C16 1.381(3) . ? C15 C20 1.390(4) . ? C16 C17 1.400(4) . ? C16 H16 0.9300 . ? C17 C18 1.378(4) . ? C18 C19 1.386(4) . ? C18 H18 0.9300 . ? C19 C20 1.380(4) . ? C19 H19 0.9300 . ? N1 C21 1.332(4) . ? N1 C25 1.339(4) . ? N2 C28 1.337(4) . ? N2 C29 1.345(4) . ? C21 C22 1.369(4) . ? C21 H21 0.9300 . ? C22 C23 1.398(4) . ? C22 H22 0.9300 . ? C23 C24 1.384(4) . ? C23 C26 1.482(4) . ? C24 C25 1.367(5) . ? C24 H24 0.9300 . ? C25 H25 0.9300 . ? C26 C30 1.384(4) . ? C26 C27 1.399(4) . ? C27 C28 1.367(5) . ? C27 H27 0.9300 . ? C28 H28 0.9300 . ? C29 C30 1.373(5) . ? C29 H29 0.9300 . ? C30 H30 0.9300 . ? O4 C31 1.208(5) . ? C31 C32 1.481(5) 2_655 ? C31 C32 1.481(5) . ? C32 H32A 0.9600 . ? C32 H32B 0.9600 . ? C32 H32C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C3 O1 H1 109.5 . . ? C11 O2 H2 109.5 . . ? C17 O3 H3 109.5 . . ? C2 C1 C6 121.0(2) . . ? C2 C1 C14 125.3(2) . . ? C6 C1 C14 113.7(2) . . ? C1 C2 C3 119.4(3) . . ? C1 C2 H2A 120.3 . . ? C3 C2 H2A 120.3 . . ? O1 C3 C4 118.8(3) . . ? O1 C3 C2 121.5(3) . . ? C4 C3 C2 119.7(3) . . ? C3 C4 C5 120.4(3) . . ? C3 C4 H4 119.8 . . ? C5 C4 H4 119.8 . . ? C6 C5 C4 120.8(3) . . ? C6 C5 H5 119.6 . . ? C4 C5 H5 119.6 . . ? C5 C6 C1 118.6(3) . . ? C5 C6 C7 129.1(2) . . ? C1 C6 C7 112.3(2) . . ? C8 C7 C6 105.0(2) . . ? C8 C7 C20 106.5(2) . . ? C6 C7 C20 105.7(2) . . ? C8 C7 H7 113.0 . . ? C6 C7 H7 113.0 . . ? C20 C7 H7 113.0 . . ? C9 C8 C13 119.4(2) . . ? C9 C8 C7 128.0(2) . . ? C13 C8 C7 112.5(2) . . ? C8 C9 C10 120.0(3) . . ? C8 C9 H9 120.0 . . ? C10 C9 H9 120.0 . . ? C11 C10 C9 120.1(3) . . ? C11 C10 H10 120.0 . . ? C9 C10 H10 120.0 . . ? O2 C11 C10 118.5(3) . . ? O2 C11 C12 121.1(3) . . ? C10 C11 C12 120.4(3) . . ? C13 C12 C11 119.1(3) . . ? C13 C12 H12 120.4 . . ? C11 C12 H12 120.4 . . ? C12 C13 C8 121.0(2) . . ? C12 C13 C14 126.0(2) . . ? C8 C13 C14 113.0(2) . . ? C1 C14 C13 105.09(19) . . ? C1 C14 C15 105.6(2) . . ? C13 C14 C15 106.8(2) . . ? C1 C14 H14 112.9 . . ? C13 C14 H14 112.9 . . ? C15 C14 H14 112.9 . . ? C16 C15 C20 121.1(3) . . ? C16 C15 C14 125.9(2) . . ? C20 C15 C14 112.9(2) . . ? C15 C16 C17 119.3(2) . . ? C15 C16 H16 120.4 . . ? C17 C16 H16 120.4 . . ? O3 C17 C18 118.3(3) . . ? O3 C17 C16 122.0(3) . . ? C18 C17 C16 119.7(3) . . ? C17 C18 C19 120.4(3) . . ? C17 C18 H18 119.8 . . ? C19 C18 H18 119.8 . . ? C20 C19 C18 120.5(3) . . ? C20 C19 H19 119.8 . . ? C18 C19 H19 119.8 . . ? C19 C20 C15 119.0(3) . . ? C19 C20 C7 127.7(2) . . ? C15 C20 C7 113.2(3) . . ? C21 N1 C25 116.1(3) . . ? C28 N2 C29 115.9(3) . . ? N1 C21 C22 123.7(3) . . ? N1 C21 H21 118.1 . . ? C22 C21 H21 118.1 . . ? C21 C22 C23 120.0(3) . . ? C21 C22 H22 120.0 . . ? C23 C22 H22 120.0 . . ? C24 C23 C22 116.2(3) . . ? C24 C23 C26 122.6(3) . . ? C22 C23 C26 121.2(3) . . ? C25 C24 C23 119.8(3) . . ? C25 C24 H24 120.1 . . ? C23 C24 H24 120.1 . . ? N1 C25 C24 124.2(3) . . ? N1 C25 H25 117.9 . . ? C24 C25 H25 117.9 . . ? C30 C26 C27 116.5(3) . . ? C30 C26 C23 121.9(3) . . ? C27 C26 C23 121.6(3) . . ? C28 C27 C26 119.4(3) . . ? C28 C27 H27 120.3 . . ? C26 C27 H27 120.3 . . ? N2 C28 C27 124.4(3) . . ? N2 C28 H28 117.8 . . ? C27 C28 H28 117.8 . . ? N2 C29 C30 123.5(3) . . ? N2 C29 H29 118.2 . . ? C30 C29 H29 118.2 . . ? C29 C30 C26 120.2(3) . . ? C29 C30 H30 119.9 . . ? C26 C30 H30 119.9 . . ? O4 C31 C32 121.3(2) . 2_655 ? O4 C31 C32 121.3(2) . . ? C32 C31 C32 117.4(5) 2_655 . ? C31 C32 H32A 109.5 . . ? C31 C32 H32B 109.5 . . ? H32A C32 H32B 109.5 . . ? C31 C32 H32C 109.5 . . ? H32A C32 H32C 109.5 . . ? H32B C32 H32C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C1 C2 C3 0.3(4) . . . . ? C14 C1 C2 C3 -178.7(3) . . . . ? C1 C2 C3 O1 -179.1(3) . . . . ? C1 C2 C3 C4 1.4(5) . . . . ? O1 C3 C4 C5 178.8(3) . . . . ? C2 C3 C4 C5 -1.7(5) . . . . ? C3 C4 C5 C6 0.4(5) . . . . ? C4 C5 C6 C1 1.3(5) . . . . ? C4 C5 C6 C7 -179.8(3) . . . . ? C2 C1 C6 C5 -1.7(4) . . . . ? C14 C1 C6 C5 177.4(2) . . . . ? C2 C1 C6 C7 179.3(3) . . . . ? C14 C1 C6 C7 -1.6(3) . . . . ? C5 C6 C7 C8 -121.2(3) . . . . ? C1 C6 C7 C8 57.8(3) . . . . ? C5 C6 C7 C20 126.4(3) . . . . ? C1 C6 C7 C20 -54.7(3) . . . . ? C6 C7 C8 C9 120.5(3) . . . . ? C20 C7 C8 C9 -127.6(3) . . . . ? C6 C7 C8 C13 -56.2(3) . . . . ? C20 C7 C8 C13 55.7(3) . . . . ? C13 C8 C9 C10 0.6(4) . . . . ? C7 C8 C9 C10 -176.0(3) . . . . ? C8 C9 C10 C11 0.6(4) . . . . ? C9 C10 C11 O2 178.3(3) . . . . ? C9 C10 C11 C12 -1.7(4) . . . . ? O2 C11 C12 C13 -178.3(2) . . . . ? C10 C11 C12 C13 1.8(4) . . . . ? C11 C12 C13 C8 -0.6(4) . . . . ? C11 C12 C13 C14 176.5(2) . . . . ? C9 C8 C13 C12 -0.5(4) . . . . ? C7 C8 C13 C12 176.5(2) . . . . ? C9 C8 C13 C14 -178.0(2) . . . . ? C7 C8 C13 C14 -1.0(3) . . . . ? C2 C1 C14 C13 123.5(3) . . . . ? C6 C1 C14 C13 -55.6(3) . . . . ? C2 C1 C14 C15 -123.8(3) . . . . ? C6 C1 C14 C15 57.1(3) . . . . ? C12 C13 C14 C1 -120.5(3) . . . . ? C8 C13 C14 C1 56.8(3) . . . . ? C12 C13 C14 C15 127.7(3) . . . . ? C8 C13 C14 C15 -55.0(3) . . . . ? C1 C14 C15 C16 122.4(3) . . . . ? C13 C14 C15 C16 -126.1(2) . . . . ? C1 C14 C15 C20 -55.3(3) . . . . ? C13 C14 C15 C20 56.2(3) . . . . ? C20 C15 C16 C17 -0.3(4) . . . . ? C14 C15 C16 C17 -177.8(2) . . . . ? C15 C16 C17 O3 -179.8(2) . . . . ? C15 C16 C17 C18 0.3(4) . . . . ? O3 C17 C18 C19 179.9(2) . . . . ? C16 C17 C18 C19 -0.2(4) . . . . ? C17 C18 C19 C20 0.1(4) . . . . ? C18 C19 C20 C15 -0.1(4) . . . . ? C18 C19 C20 C7 178.8(3) . . . . ? C16 C15 C20 C19 0.2(4) . . . . ? C14 C15 C20 C19 178.0(2) . . . . ? C16 C15 C20 C7 -178.8(2) . . . . ? C14 C15 C20 C7 -1.0(3) . . . . ? C8 C7 C20 C19 126.2(3) . . . . ? C6 C7 C20 C19 -122.4(3) . . . . ? C8 C7 C20 C15 -54.8(3) . . . . ? C6 C7 C20 C15 56.5(3) . . . . ? C25 N1 C21 C22 -1.2(4) . . . . ? N1 C21 C22 C23 1.2(5) . . . . ? C21 C22 C23 C24 -0.4(4) . . . . ? C21 C22 C23 C26 -178.4(3) . . . . ? C22 C23 C24 C25 -0.2(5) . . . . ? C26 C23 C24 C25 177.7(3) . . . . ? C21 N1 C25 C24 0.5(5) . . . . ? C23 C24 C25 N1 0.2(5) . . . . ? C24 C23 C26 C30 149.0(3) . . . . ? C22 C23 C26 C30 -33.2(4) . . . . ? C24 C23 C26 C27 -32.1(4) . . . . ? C22 C23 C26 C27 145.7(3) . . . . ? C30 C26 C27 C28 1.2(5) . . . . ? C23 C26 C27 C28 -177.7(3) . . . . ? C29 N2 C28 C27 1.1(5) . . . . ? C26 C27 C28 N2 -2.0(5) . . . . ? C28 N2 C29 C30 0.5(5) . . . . ? N2 C29 C30 C26 -1.2(5) . . . . ? C27 C26 C30 C29 0.3(4) . . . . ? C23 C26 C30 C29 179.2(3) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.02 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.183 _refine_diff_density_min -0.208 _refine_diff_density_rms 0.043 # Attachment '2c.cif' data_61224e _database_code_depnum_ccdc_archive 'CCDC 760764' #TrackingRef '2c.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C40 H30 N4 O3' _chemical_formula_weight 614.68 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)/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 12.7629(17) _cell_length_b 15.811(2) _cell_length_c 16.351(2) _cell_angle_alpha 90.00 _cell_angle_beta 97.546(2) _cell_angle_gamma 90.00 _cell_volume 3271.1(8) _cell_formula_units_Z 4 _cell_measurement_temperature 294(2) _cell_measurement_reflns_used 3752 _cell_measurement_theta_min 2.30 _cell_measurement_theta_max 22.17 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.248 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1288 _exptl_absorpt_coefficient_mu 0.080 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9810 _exptl_absorpt_correction_T_max 0.9857 _exptl_absorpt_process_details sadabs _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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 18543 _diffrn_reflns_av_R_equivalents 0.0381 _diffrn_reflns_av_sigmaI/netI 0.0492 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.80 _diffrn_reflns_theta_max 26.43 _reflns_number_total 6707 _reflns_number_gt 3005 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0581P)^2^+0.6880P] 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 none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6707 _refine_ls_number_parameters 433 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.1266 _refine_ls_R_factor_gt 0.0485 _refine_ls_wR_factor_ref 0.1554 _refine_ls_wR_factor_gt 0.1167 _refine_ls_goodness_of_fit_ref 0.981 _refine_ls_restrained_S_all 0.980 _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 N1 N 0.0678(2) 0.80016(16) 0.04408(14) 0.0875(7) Uani 1 1 d . . . N2 N 0.1952(2) 0.80269(16) 0.48059(14) 0.0870(7) Uani 1 1 d . . . N3 N 0.6966(4) 0.9809(3) -0.0138(2) 0.1704(17) Uani 1 1 d . . . N4 N 0.8350(2) 0.9283(2) 0.41708(15) 0.0937(8) Uani 1 1 d . . . O1 O 0.40303(15) 0.58317(15) 0.08345(12) 0.1005(7) Uani 1 1 d D . . H1A H 0.380(3) 0.582(2) 0.0327(15) 0.151 Uiso 1 1 d D . . O2 O -0.24305(18) 0.70837(14) 0.15015(12) 0.0993(7) Uani 1 1 d D . . H2 H -0.261(3) 0.699(2) 0.0990(15) 0.149 Uiso 1 1 d D . . O3 O -0.0504(2) 0.18641(13) 0.12861(12) 0.1024(7) Uani 1 1 d D . . H3A H -0.054(3) 0.193(2) 0.0770(15) 0.154 Uiso 1 1 d D . . C1 C 0.03895(17) 0.49366(14) 0.12553(12) 0.0569(6) Uani 1 1 d . . . H1 H 0.0194 0.4935 0.0655 0.068 Uiso 1 1 calc R . . C2 C 0.15422(18) 0.51747(14) 0.15118(13) 0.0579(6) Uani 1 1 d . . . C3 C 0.22670(19) 0.53792(15) 0.09885(14) 0.0643(6) Uani 1 1 d . . . H3 H 0.2072 0.5376 0.0420 0.077 Uiso 1 1 calc R . . C4 C 0.3294(2) 0.55906(17) 0.13213(16) 0.0742(7) Uani 1 1 d . . . C5 C 0.3578(2) 0.55747(17) 0.21698(17) 0.0787(8) Uani 1 1 d . . . H5 H 0.4267 0.5706 0.2392 0.094 Uiso 1 1 calc R . . C6 C 0.2846(2) 0.53656(16) 0.26889(15) 0.0721(7) Uani 1 1 d . . . H6 H 0.3046 0.5357 0.3257 0.086 Uiso 1 1 calc R . . C7 C 0.18195(19) 0.51700(15) 0.23690(13) 0.0613(6) Uani 1 1 d . . . C8 C 0.09102(19) 0.49330(15) 0.28336(13) 0.0627(6) Uani 1 1 d . . . H8 H 0.1108 0.4933 0.3433 0.075 Uiso 1 1 calc R . . C9 C 0.00185(19) 0.55529(15) 0.25494(13) 0.0601(6) Uani 1 1 d . . . C10 C -0.0512(2) 0.60739(16) 0.30266(15) 0.0728(7) Uani 1 1 d . . . H10 H -0.0324 0.6084 0.3596 0.087 Uiso 1 1 calc R . . C11 C -0.1323(2) 0.65832(17) 0.26657(16) 0.0799(8) Uani 1 1 d . . . H11 H -0.1681 0.6932 0.2993 0.096 Uiso 1 1 calc R . . C12 C -0.1605(2) 0.65763(17) 0.18169(16) 0.0726(7) Uani 1 1 d . . . C13 C -0.10722(19) 0.60625(15) 0.13261(14) 0.0623(6) Uani 1 1 d . . . H13 H -0.1256 0.6060 0.0757 0.075 Uiso 1 1 calc R . . C14 C -0.02665(18) 0.55541(14) 0.16905(13) 0.0565(6) Uani 1 1 d . . . C15 C 0.02524(17) 0.40747(15) 0.16419(13) 0.0560(6) Uani 1 1 d . . . C16 C -0.00907(18) 0.33505(15) 0.12268(14) 0.0625(6) Uani 1 1 d . . . H16 H -0.0266 0.3358 0.0657 0.075 Uiso 1 1 calc R . . C17 C -0.0173(2) 0.26043(17) 0.16677(16) 0.0713(7) Uani 1 1 d . . . C18 C 0.0077(2) 0.26009(17) 0.25172(16) 0.0774(8) Uani 1 1 d . . . H18 H 0.0003 0.2107 0.2813 0.093 Uiso 1 1 calc R . . C19 C 0.0439(2) 0.33367(17) 0.29289(14) 0.0689(7) Uani 1 1 d . . . H19 H 0.0622 0.3328 0.3498 0.083 Uiso 1 1 calc R . . C20 C 0.05274(18) 0.40765(15) 0.24997(13) 0.0593(6) Uani 1 1 d . . . C21 C 0.1469(3) 0.7571(2) 0.0826(2) 0.1056(11) Uani 1 1 d . . . H21 H 0.1890 0.7269 0.0506 0.127 Uiso 1 1 calc R . . C22 C 0.1724(2) 0.7533(2) 0.16740(18) 0.0964(10) Uani 1 1 d . . . H22 H 0.2288 0.7200 0.1905 0.116 Uiso 1 1 calc R . . C23 C 0.1149(2) 0.79817(15) 0.21711(15) 0.0651(7) Uani 1 1 d . . . C24 C 0.0307(2) 0.8421(2) 0.17671(18) 0.1012(10) Uani 1 1 d . . . H24 H -0.0133 0.8727 0.2068 0.121 Uiso 1 1 calc R . . C25 C 0.0112(3) 0.8410(2) 0.0920(2) 0.1076(11) Uani 1 1 d . . . H25 H -0.0466 0.8717 0.0670 0.129 Uiso 1 1 calc R . . C26 C 0.2585(3) 0.7744(3) 0.4315(2) 0.1170(12) Uani 1 1 d . . . H26 H 0.3241 0.7545 0.4552 0.140 Uiso 1 1 calc R . . C27 C 0.2364(2) 0.7713(2) 0.34649(19) 0.1128(12) Uani 1 1 d . . . H27 H 0.2866 0.7503 0.3154 0.135 Uiso 1 1 calc R . . C28 C 0.14195(19) 0.79885(16) 0.30816(15) 0.0647(6) Uani 1 1 d . . . C29 C 0.0740(3) 0.8288(2) 0.35970(18) 0.1027(11) Uani 1 1 d . . . H29 H 0.0080 0.8493 0.3376 0.123 Uiso 1 1 calc R . . C30 C 0.1024(3) 0.8290(2) 0.4440(2) 0.1075(11) Uani 1 1 d . . . H30 H 0.0536 0.8487 0.4770 0.129 Uiso 1 1 calc R . . C31 C 0.6526(4) 0.9238(3) 0.0282(2) 0.1432(16) Uani 1 1 d . . . H31 H 0.6008 0.8896 -0.0003 0.172 Uiso 1 1 calc R . . C32 C 0.6775(3) 0.9107(2) 0.11156(17) 0.1016(10) Uani 1 1 d . . . H32 H 0.6429 0.8690 0.1378 0.122 Uiso 1 1 calc R . . C33 C 0.7535(2) 0.95938(17) 0.15577(16) 0.0733(7) Uani 1 1 d . . . C34 C 0.8005(3) 1.0184(2) 0.1123(2) 0.1348(15) Uani 1 1 d . . . H34 H 0.8533 1.0531 0.1387 0.162 Uiso 1 1 calc R . . C35 C 0.7693(5) 1.0265(3) 0.0291(3) 0.190(2) Uani 1 1 d . . . H35 H 0.8027 1.0676 0.0011 0.228 Uiso 1 1 calc R . . C36 C 0.7791(2) 0.8714(2) 0.37059(18) 0.0940(9) Uani 1 1 d . . . H36 H 0.7571 0.8233 0.3963 0.113 Uiso 1 1 calc R . . C37 C 0.7514(2) 0.8789(2) 0.28674(16) 0.0834(8) Uani 1 1 d . . . H37 H 0.7121 0.8365 0.2577 0.100 Uiso 1 1 calc R . . C38 C 0.78150(19) 0.94868(17) 0.24577(15) 0.0654(6) Uani 1 1 d . . . C39 C 0.8399(2) 1.00889(19) 0.29362(19) 0.0876(8) Uani 1 1 d . . . H39 H 0.8629 1.0576 0.2695 0.105 Uiso 1 1 calc R . . C40 C 0.8636(3) 0.9957(3) 0.3775(2) 0.1023(11) Uani 1 1 d . . . H40 H 0.9024 1.0372 0.4084 0.123 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.112(2) 0.0793(16) 0.0682(15) -0.0112(13) -0.0003(15) 0.0008(15) N2 0.0812(17) 0.1096(19) 0.0686(15) -0.0119(13) 0.0036(15) -0.0126(15) N3 0.267(5) 0.169(4) 0.069(2) 0.028(2) -0.002(3) -0.037(3) N4 0.0746(16) 0.140(3) 0.0657(16) -0.0280(17) 0.0074(13) 0.0138(17) O1 0.0726(13) 0.152(2) 0.0753(13) 0.0177(14) 0.0061(11) -0.0258(12) O2 0.1167(16) 0.1054(16) 0.0717(12) -0.0052(12) -0.0022(12) 0.0365(13) O3 0.1497(19) 0.0695(13) 0.0851(14) -0.0082(11) 0.0050(15) -0.0214(12) C1 0.0663(15) 0.0694(15) 0.0326(11) 0.0013(10) -0.0028(11) -0.0066(12) C2 0.0629(15) 0.0639(15) 0.0442(13) 0.0024(11) -0.0031(12) -0.0057(12) C3 0.0674(16) 0.0782(17) 0.0452(13) 0.0048(12) -0.0004(12) -0.0068(13) C4 0.0656(17) 0.091(2) 0.0643(17) 0.0090(14) 0.0032(14) -0.0113(15) C5 0.0675(17) 0.095(2) 0.0685(18) 0.0065(15) -0.0122(15) -0.0151(15) C6 0.0808(19) 0.0818(19) 0.0486(14) 0.0023(12) -0.0098(14) -0.0072(15) C7 0.0676(16) 0.0706(16) 0.0424(13) 0.0015(11) -0.0047(12) -0.0071(12) C8 0.0780(17) 0.0749(17) 0.0323(12) 0.0000(11) -0.0030(11) -0.0064(14) C9 0.0754(16) 0.0637(15) 0.0396(13) -0.0022(11) 0.0018(12) -0.0082(13) C10 0.097(2) 0.0735(18) 0.0458(14) -0.0043(13) 0.0011(14) -0.0048(16) C11 0.107(2) 0.0767(19) 0.0558(17) -0.0107(13) 0.0078(15) 0.0102(17) C12 0.0846(19) 0.0703(18) 0.0603(17) 0.0010(13) -0.0004(14) 0.0067(15) C13 0.0738(16) 0.0684(16) 0.0431(13) 0.0002(12) 0.0016(12) -0.0054(13) C14 0.0674(15) 0.0616(15) 0.0390(13) 0.0025(10) 0.0013(11) -0.0089(12) C15 0.0597(14) 0.0657(16) 0.0419(12) 0.0016(11) 0.0032(10) -0.0031(12) C16 0.0708(16) 0.0675(16) 0.0476(13) -0.0027(12) 0.0022(12) -0.0030(13) C17 0.0847(19) 0.0628(17) 0.0655(17) -0.0042(13) 0.0061(14) -0.0050(14) C18 0.096(2) 0.0684(18) 0.0683(18) 0.0124(14) 0.0127(15) 0.0014(15) C19 0.0836(18) 0.0775(18) 0.0445(14) 0.0086(13) 0.0039(12) 0.0063(15) C20 0.0671(15) 0.0702(16) 0.0393(12) 0.0042(11) 0.0022(11) -0.0017(13) C21 0.128(3) 0.114(3) 0.075(2) -0.0177(18) 0.015(2) 0.030(2) C22 0.106(2) 0.110(2) 0.071(2) -0.0099(17) -0.0013(18) 0.0360(19) C23 0.0644(16) 0.0644(16) 0.0650(17) -0.0129(13) 0.0029(14) -0.0072(13) C24 0.084(2) 0.142(3) 0.074(2) -0.0243(19) -0.0024(17) 0.032(2) C25 0.102(2) 0.135(3) 0.079(2) -0.017(2) -0.0137(19) 0.028(2) C26 0.073(2) 0.197(4) 0.078(2) 0.010(2) 0.0017(18) 0.027(2) C27 0.073(2) 0.196(4) 0.070(2) -0.003(2) 0.0113(17) 0.032(2) C28 0.0564(15) 0.0701(16) 0.0668(17) -0.0096(13) 0.0053(13) -0.0052(13) C29 0.094(2) 0.135(3) 0.076(2) -0.0343(18) -0.0044(18) 0.032(2) C30 0.103(3) 0.139(3) 0.078(2) -0.0365(19) 0.007(2) 0.021(2) C31 0.195(4) 0.154(4) 0.071(2) 0.011(2) -0.021(3) -0.036(3) C32 0.126(3) 0.115(3) 0.0592(18) 0.0038(17) -0.0065(17) -0.025(2) C33 0.0850(19) 0.0748(18) 0.0607(17) -0.0040(14) 0.0116(15) -0.0046(15) C34 0.183(4) 0.132(3) 0.088(3) 0.016(2) 0.016(3) -0.067(3) C35 0.296(7) 0.179(5) 0.093(4) 0.045(3) 0.023(4) -0.084(5) C36 0.088(2) 0.129(3) 0.065(2) 0.0017(18) 0.0119(16) -0.0080(19) C37 0.091(2) 0.101(2) 0.0579(17) -0.0018(15) 0.0051(15) -0.0196(17) C38 0.0578(15) 0.0768(18) 0.0626(16) -0.0111(14) 0.0112(12) -0.0004(13) C39 0.083(2) 0.091(2) 0.088(2) -0.0181(17) 0.0067(17) -0.0082(16) C40 0.087(2) 0.118(3) 0.097(3) -0.045(2) -0.008(2) 0.002(2) _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 1.305(4) . ? N1 C21 1.308(4) . ? N2 C26 1.291(4) . ? N2 C30 1.322(4) . ? N3 C35 1.304(6) . ? N3 C31 1.305(5) . ? N4 C40 1.324(4) . ? N4 C36 1.324(4) . ? O1 C4 1.363(3) . ? O1 H1A 0.84(2) . ? O2 C12 1.370(3) . ? O2 H2 0.85(2) . ? O3 C17 1.367(3) . ? O3 H3A 0.85(2) . ? C1 C15 1.522(3) . ? C1 C14 1.522(3) . ? C1 C2 1.523(3) . ? C1 H1 0.9800 . ? C2 C3 1.379(3) . ? C2 C7 1.400(3) . ? C3 C4 1.393(3) . ? C3 H3 0.9300 . ? C4 C5 1.387(3) . ? C5 C6 1.382(3) . ? C5 H5 0.9300 . ? C6 C7 1.380(3) . ? C6 H6 0.9300 . ? C7 C8 1.515(3) . ? C8 C20 1.517(3) . ? C8 C9 1.527(3) . ? C8 H8 0.9800 . ? C9 C10 1.373(3) . ? C9 C14 1.404(3) . ? C10 C11 1.381(3) . ? C10 H10 0.9300 . ? C11 C12 1.387(3) . ? C11 H11 0.9300 . ? C12 C13 1.382(3) . ? C13 C14 1.378(3) . ? C13 H13 0.9300 . ? C15 C16 1.373(3) . ? C15 C20 1.401(3) . ? C16 C17 1.394(3) . ? C16 H16 0.9300 . ? C17 C18 1.384(3) . ? C18 C19 1.392(3) . ? C18 H18 0.9300 . ? C19 C20 1.376(3) . ? C19 H19 0.9300 . ? C21 C22 1.384(4) . ? C21 H21 0.9300 . ? C22 C23 1.364(3) . ? C22 H22 0.9300 . ? C23 C24 1.373(3) . ? C23 C28 1.483(3) . ? C24 C25 1.375(4) . ? C24 H24 0.9300 . ? C25 H25 0.9300 . ? C26 C27 1.383(4) . ? C26 H26 0.9300 . ? C27 C28 1.355(3) . ? C27 H27 0.9300 . ? C28 C29 1.371(4) . ? C29 C30 1.378(4) . ? C29 H29 0.9300 . ? C30 H30 0.9300 . ? C31 C32 1.374(4) . ? C31 H31 0.9300 . ? C32 C33 1.368(4) . ? C32 H32 0.9300 . ? C33 C34 1.359(4) . ? C33 C38 1.478(3) . ? C34 C35 1.373(5) . ? C34 H34 0.9300 . ? C35 H35 0.9300 . ? C36 C37 1.375(3) . ? C36 H36 0.9300 . ? C37 C38 1.371(3) . ? C37 H37 0.9300 . ? C38 C39 1.386(3) . ? C39 C40 1.381(4) . ? C39 H39 0.9300 . ? C40 H40 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 C25 N1 C21 115.0(3) . . ? C26 N2 C30 115.1(3) . . ? C35 N3 C31 115.2(4) . . ? C40 N4 C36 115.4(3) . . ? C4 O1 H1A 113(3) . . ? C12 O2 H2 111(3) . . ? C17 O3 H3A 109(3) . . ? C15 C1 C14 106.25(18) . . ? C15 C1 C2 105.46(17) . . ? C14 C1 C2 106.46(18) . . ? C15 C1 H1 112.7 . . ? C14 C1 H1 112.7 . . ? C2 C1 H1 112.7 . . ? C3 C2 C7 121.4(2) . . ? C3 C2 C1 126.1(2) . . ? C7 C2 C1 112.5(2) . . ? C2 C3 C4 119.2(2) . . ? C2 C3 H3 120.4 . . ? C4 C3 H3 120.4 . . ? O1 C4 C5 118.7(2) . . ? O1 C4 C3 121.6(2) . . ? C5 C4 C3 119.7(2) . . ? C6 C5 C4 120.7(2) . . ? C6 C5 H5 119.7 . . ? C4 C5 H5 119.7 . . ? C7 C6 C5 120.3(2) . . ? C7 C6 H6 119.8 . . ? C5 C6 H6 119.8 . . ? C6 C7 C2 118.7(2) . . ? C6 C7 C8 128.1(2) . . ? C2 C7 C8 113.2(2) . . ? C7 C8 C20 105.79(19) . . ? C7 C8 C9 106.13(18) . . ? C20 C8 C9 105.75(18) . . ? C7 C8 H8 112.8 . . ? C20 C8 H8 112.8 . . ? C9 C8 H8 112.8 . . ? C10 C9 C14 119.1(2) . . ? C10 C9 C8 128.0(2) . . ? C14 C9 C8 113.0(2) . . ? C9 C10 C11 120.3(2) . . ? C9 C10 H10 119.8 . . ? C11 C10 H10 119.8 . . ? C10 C11 C12 120.3(3) . . ? C10 C11 H11 119.9 . . ? C12 C11 H11 119.9 . . ? O2 C12 C13 122.6(2) . . ? O2 C12 C11 117.2(2) . . ? C13 C12 C11 120.2(2) . . ? C14 C13 C12 119.2(2) . . ? C14 C13 H13 120.4 . . ? C12 C13 H13 120.4 . . ? C13 C14 C9 120.9(2) . . ? C13 C14 C1 126.67(19) . . ? C9 C14 C1 112.4(2) . . ? C16 C15 C20 121.2(2) . . ? C16 C15 C1 126.0(2) . . ? C20 C15 C1 112.8(2) . . ? C15 C16 C17 119.4(2) . . ? C15 C16 H16 120.3 . . ? C17 C16 H16 120.3 . . ? O3 C17 C18 118.1(2) . . ? O3 C17 C16 121.9(2) . . ? C18 C17 C16 120.0(2) . . ? C17 C18 C19 120.0(2) . . ? C17 C18 H18 120.0 . . ? C19 C18 H18 120.0 . . ? C20 C19 C18 120.5(2) . . ? C20 C19 H19 119.7 . . ? C18 C19 H19 119.7 . . ? C19 C20 C15 118.8(2) . . ? C19 C20 C8 128.3(2) . . ? C15 C20 C8 112.9(2) . . ? N1 C21 C22 124.8(3) . . ? N1 C21 H21 117.6 . . ? C22 C21 H21 117.6 . . ? C23 C22 C21 120.0(3) . . ? C23 C22 H22 120.0 . . ? C21 C22 H22 120.0 . . ? C22 C23 C24 115.1(2) . . ? C22 C23 C28 121.9(2) . . ? C24 C23 C28 122.9(2) . . ? C23 C24 C25 120.4(3) . . ? C23 C24 H24 119.8 . . ? C25 C24 H24 119.8 . . ? N1 C25 C24 124.7(3) . . ? N1 C25 H25 117.7 . . ? C24 C25 H25 117.7 . . ? N2 C26 C27 125.1(3) . . ? N2 C26 H26 117.5 . . ? C27 C26 H26 117.5 . . ? C28 C27 C26 120.4(3) . . ? C28 C27 H27 119.8 . . ? C26 C27 H27 119.8 . . ? C27 C28 C29 115.0(3) . . ? C27 C28 C23 122.5(2) . . ? C29 C28 C23 122.4(2) . . ? C28 C29 C30 120.7(3) . . ? C28 C29 H29 119.7 . . ? C30 C29 H29 119.7 . . ? N2 C30 C29 123.7(3) . . ? N2 C30 H30 118.2 . . ? C29 C30 H30 118.2 . . ? N3 C31 C32 124.5(4) . . ? N3 C31 H31 117.8 . . ? C32 C31 H31 117.8 . . ? C33 C32 C31 119.7(3) . . ? C33 C32 H32 120.1 . . ? C31 C32 H32 120.1 . . ? C34 C33 C32 116.1(3) . . ? C34 C33 C38 122.3(3) . . ? C32 C33 C38 121.6(3) . . ? C33 C34 C35 119.5(4) . . ? C33 C34 H34 120.3 . . ? C35 C34 H34 120.3 . . ? N3 C35 C34 125.0(4) . . ? N3 C35 H35 117.5 . . ? C34 C35 H35 117.5 . . ? N4 C36 C37 124.2(3) . . ? N4 C36 H36 117.9 . . ? C37 C36 H36 117.9 . . ? C38 C37 C36 120.3(3) . . ? C38 C37 H37 119.8 . . ? C36 C37 H37 119.8 . . ? C37 C38 C39 116.2(3) . . ? C37 C38 C33 122.1(2) . . ? C39 C38 C33 121.7(3) . . ? C40 C39 C38 119.2(3) . . ? C40 C39 H39 120.4 . . ? C38 C39 H39 120.4 . . ? N4 C40 C39 124.6(3) . . ? N4 C40 H40 117.7 . . ? C39 C40 H40 117.7 . . ? 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 C15 C1 C2 C3 123.9(2) . . . . ? C14 C1 C2 C3 -123.5(2) . . . . ? C15 C1 C2 C7 -56.2(2) . . . . ? C14 C1 C2 C7 56.4(2) . . . . ? C7 C2 C3 C4 -0.4(4) . . . . ? C1 C2 C3 C4 179.5(2) . . . . ? C2 C3 C4 O1 -177.2(2) . . . . ? C2 C3 C4 C5 1.4(4) . . . . ? O1 C4 C5 C6 177.5(3) . . . . ? C3 C4 C5 C6 -1.2(4) . . . . ? C4 C5 C6 C7 -0.1(4) . . . . ? C5 C6 C7 C2 1.0(4) . . . . ? C5 C6 C7 C8 -179.6(2) . . . . ? C3 C2 C7 C6 -0.8(4) . . . . ? C1 C2 C7 C6 179.3(2) . . . . ? C3 C2 C7 C8 179.7(2) . . . . ? C1 C2 C7 C8 -0.2(3) . . . . ? C6 C7 C8 C20 -123.1(3) . . . . ? C2 C7 C8 C20 56.4(2) . . . . ? C6 C7 C8 C9 124.9(3) . . . . ? C2 C7 C8 C9 -55.7(2) . . . . ? C7 C8 C9 C10 -124.9(3) . . . . ? C20 C8 C9 C10 123.1(3) . . . . ? C7 C8 C9 C14 55.9(2) . . . . ? C20 C8 C9 C14 -56.1(2) . . . . ? C14 C9 C10 C11 0.8(4) . . . . ? C8 C9 C10 C11 -178.3(2) . . . . ? C9 C10 C11 C12 -0.4(4) . . . . ? C10 C11 C12 O2 178.7(2) . . . . ? C10 C11 C12 C13 -0.3(4) . . . . ? O2 C12 C13 C14 -178.4(2) . . . . ? C11 C12 C13 C14 0.5(4) . . . . ? C12 C13 C14 C9 -0.1(3) . . . . ? C12 C13 C14 C1 178.6(2) . . . . ? C10 C9 C14 C13 -0.6(3) . . . . ? C8 C9 C14 C13 178.7(2) . . . . ? C10 C9 C14 C1 -179.5(2) . . . . ? C8 C9 C14 C1 -0.2(3) . . . . ? C15 C1 C14 C13 -122.6(2) . . . . ? C2 C1 C14 C13 125.3(2) . . . . ? C15 C1 C14 C9 56.2(2) . . . . ? C2 C1 C14 C9 -55.9(2) . . . . ? C14 C1 C15 C16 124.7(2) . . . . ? C2 C1 C15 C16 -122.5(2) . . . . ? C14 C1 C15 C20 -55.9(2) . . . . ? C2 C1 C15 C20 56.9(2) . . . . ? C20 C15 C16 C17 0.4(4) . . . . ? C1 C15 C16 C17 179.8(2) . . . . ? C15 C16 C17 O3 -179.6(2) . . . . ? C15 C16 C17 C18 0.8(4) . . . . ? O3 C17 C18 C19 178.6(2) . . . . ? C16 C17 C18 C19 -1.8(4) . . . . ? C17 C18 C19 C20 1.5(4) . . . . ? C18 C19 C20 C15 -0.3(4) . . . . ? C18 C19 C20 C8 -179.5(2) . . . . ? C16 C15 C20 C19 -0.7(4) . . . . ? C1 C15 C20 C19 179.9(2) . . . . ? C16 C15 C20 C8 178.6(2) . . . . ? C1 C15 C20 C8 -0.9(3) . . . . ? C7 C8 C20 C19 123.5(3) . . . . ? C9 C8 C20 C19 -124.2(3) . . . . ? C7 C8 C20 C15 -55.7(2) . . . . ? C9 C8 C20 C15 56.6(3) . . . . ? C25 N1 C21 C22 -0.2(5) . . . . ? N1 C21 C22 C23 -1.7(5) . . . . ? C21 C22 C23 C24 2.7(4) . . . . ? C21 C22 C23 C28 -177.4(3) . . . . ? C22 C23 C24 C25 -2.0(5) . . . . ? C28 C23 C24 C25 178.1(3) . . . . ? C21 N1 C25 C24 1.1(5) . . . . ? C23 C24 C25 N1 0.1(6) . . . . ? C30 N2 C26 C27 1.0(6) . . . . ? N2 C26 C27 C28 -0.4(6) . . . . ? C26 C27 C28 C29 0.2(5) . . . . ? C26 C27 C28 C23 179.1(3) . . . . ? C22 C23 C28 C27 14.8(4) . . . . ? C24 C23 C28 C27 -165.3(3) . . . . ? C22 C23 C28 C29 -166.4(3) . . . . ? C24 C23 C28 C29 13.5(4) . . . . ? C27 C28 C29 C30 -0.6(5) . . . . ? C23 C28 C29 C30 -179.5(3) . . . . ? C26 N2 C30 C29 -1.5(5) . . . . ? C28 C29 C30 N2 1.4(5) . . . . ? C35 N3 C31 C32 0.6(8) . . . . ? N3 C31 C32 C33 -0.2(7) . . . . ? C31 C32 C33 C34 -0.5(5) . . . . ? C31 C32 C33 C38 178.8(3) . . . . ? C32 C33 C34 C35 0.7(6) . . . . ? C38 C33 C34 C35 -178.6(4) . . . . ? C31 N3 C35 C34 -0.4(9) . . . . ? C33 C34 C35 N3 -0.3(9) . . . . ? C40 N4 C36 C37 0.5(4) . . . . ? N4 C36 C37 C38 -0.2(5) . . . . ? C36 C37 C38 C39 0.0(4) . . . . ? C36 C37 C38 C33 -180.0(3) . . . . ? C34 C33 C38 C37 -166.0(3) . . . . ? C32 C33 C38 C37 14.7(4) . . . . ? C34 C33 C38 C39 14.0(4) . . . . ? C32 C33 C38 C39 -165.3(3) . . . . ? C37 C38 C39 C40 -0.2(4) . . . . ? C33 C38 C39 C40 179.8(3) . . . . ? C36 N4 C40 C39 -0.6(5) . . . . ? C38 C39 C40 N4 0.5(5) . . . . ? 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 C40 H40 O1 0.93 2.57 3.270(4) 131.9 2_655 C34 H34 O3 0.93 2.46 3.258(4) 144.4 1_665 C8 H8 N3 0.98 2.48 3.437(4) 165.1 4_576 O3 H3A N1 0.85(2) 1.97(2) 2.811(3) 175(4) 3_565 O2 H2 N2 0.85(2) 1.94(2) 2.787(3) 170(4) 4_575 O1 H1A N4 0.84(2) 1.91(2) 2.751(3) 176(4) 4_575 _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 26.43 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.170 _refine_diff_density_min -0.154 _refine_diff_density_rms 0.029