# Electronic Supplementary Material (ESI) for New Journal of Chemistry # This journal is © The Royal Society of Chemistry and The Centre National de la Recherche Scientifique 2014 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_tll01-32 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C45 H50 O10, C2 H3 N' _chemical_formula_sum 'C47 H53 N O10' _chemical_formula_weight 791.90 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 tetragonal _symmetry_space_group_name_H-M 'I 4(1)/a' _symmetry_space_group_name_HALL '-I 4ad' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-y+3/4, x+1/4, z+1/4' 'y+3/4, -x+3/4, z+3/4' 'x+1/2, y+1/2, z+1/2' '-x+1, -y+1/2, z+1' '-y+5/4, x+3/4, z+3/4' 'y+5/4, -x+5/4, z+5/4' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'y-3/4, -x-1/4, -z-1/4' '-y-3/4, x-3/4, -z-3/4' '-x+1/2, -y+1/2, -z+1/2' 'x, y+1/2, -z' 'y-1/4, -x+1/4, -z+1/4' '-y-1/4, x-1/4, -z-1/4' _cell_length_a 14.976(2) _cell_length_b 14.976(2) _cell_length_c 39.297(8) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 8814(2) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 18560 _cell_measurement_theta_min 3.09 _cell_measurement_theta_max 27.59 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.53 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.194 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 3376 _exptl_absorpt_coefficient_mu 0.083 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9570 _exptl_absorpt_correction_T_max 0.9895 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 39700 _diffrn_reflns_av_R_equivalents 0.1267 _diffrn_reflns_av_sigmaI/netI 0.0856 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -50 _diffrn_reflns_limit_l_max 50 _diffrn_reflns_theta_min 3.09 _diffrn_reflns_theta_max 27.48 _reflns_number_total 5042 _reflns_number_gt 2096 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0713P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5042 _refine_ls_number_parameters 282 _refine_ls_number_restraints 25 _refine_ls_R_factor_all 0.1983 _refine_ls_R_factor_gt 0.0840 _refine_ls_wR_factor_ref 0.1862 _refine_ls_wR_factor_gt 0.1502 _refine_ls_goodness_of_fit_ref 1.044 _refine_ls_restrained_S_all 1.044 _refine_ls_shift/su_max 0.091 _refine_ls_shift/su_mean 0.004 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.5000 0.2500 0.24408(4) 0.0708(6) Uani 1 2 d S . . H1A H 0.5351 0.2889 0.2586 0.085 Uiso 0.50 1 calc PR . . H1B H 0.4649 0.2111 0.2586 0.085 Uiso 0.50 1 calc PR . . C2 C 0.43798(8) 0.30605(8) 0.22249(3) 0.0632(4) Uani 1 1 d . . . C3 C 0.46282(8) 0.39067(8) 0.21160(3) 0.0673(4) Uani 1 1 d . . . H3 H 0.5171 0.4142 0.2188 0.081 Uiso 1 1 calc R . . C4 C 0.40909(8) 0.44055(7) 0.19047(3) 0.0646(4) Uani 1 1 d . . . C5 C 0.32681(7) 0.40903(7) 0.18009(3) 0.0606(4) Uani 1 1 d . . . C6 C 0.30078(8) 0.32491(8) 0.19160(3) 0.0700(4) Uani 1 1 d . . . H6 H 0.2452 0.3027 0.1853 0.084 Uiso 1 1 calc R . . C7 C 0.35563(8) 0.27362(8) 0.21211(3) 0.0660(4) Uani 1 1 d . . . C8 C 0.26849(8) 0.46185(8) 0.15613(3) 0.0703(4) Uani 1 1 d . . . H8A H 0.2066 0.4457 0.1599 0.084 Uiso 1 1 calc R . . H8B H 0.2749 0.5249 0.1611 0.084 Uiso 1 1 calc R . . C9 C 0.29158(7) 0.44593(7) 0.11935(3) 0.0583(4) Uani 1 1 d . . . C10 C 0.35633(7) 0.49618(7) 0.10305(3) 0.0608(4) Uani 1 1 d . . . H10 H 0.3839 0.5425 0.1148 0.073 Uiso 1 1 calc R . . C11 C 0.38095(7) 0.47920(7) 0.06983(3) 0.0573(4) Uani 1 1 d . . . C12 C 0.33873(7) 0.41302(7) 0.05108(3) 0.05829(19) Uani 1 1 d U . . C13 C 0.27328(7) 0.36361(7) 0.06744(3) 0.0600(2) Uani 1 1 d U . . H13 H 0.2434 0.3193 0.0554 0.072 Uiso 1 1 calc R . . C14 C 0.25119(7) 0.37811(7) 0.10083(3) 0.0645(4) Uani 1 1 d . . . C15 C 0.36550(8) 0.39098(7) 0.01511(3) 0.0623(4) Uani 1 1 d . . . H15A H 0.3896 0.4439 0.0042 0.075 Uiso 1 1 calc R . . H15B H 0.3133 0.3722 0.0024 0.075 Uiso 1 1 calc R . . C16 C 0.43473(7) 0.31747(7) 0.01447(3) 0.0515(3) Uani 1 1 d . . . C17 C 0.52458(7) 0.33801(7) 0.01448(3) 0.0548(3) Uani 1 1 d . . . H17 H 0.5419 0.3976 0.0142 0.066 Uiso 1 1 calc R . . C18 C 0.41055(7) 0.22766(7) 0.01492(3) 0.0510(3) Uani 1 1 d . . . C19 C 0.25555(9) 0.14835(9) 0.21017(4) 0.1089(6) Uani 1 1 d . . . H19A H 0.2041 0.1842 0.2152 0.163 Uiso 1 1 calc R . . H19B H 0.2484 0.0903 0.2202 0.163 Uiso 1 1 calc R . . H19C H 0.2619 0.1425 0.1860 0.163 Uiso 1 1 calc R . . C20 C 0.52326(9) 0.54785(10) 0.17797(4) 0.1056(6) Uani 1 1 d . . . H20A H 0.5440 0.5585 0.2007 0.158 Uiso 1 1 calc R . . H20B H 0.5311 0.6009 0.1646 0.158 Uiso 1 1 calc R . . H20C H 0.5568 0.4998 0.1681 0.158 Uiso 1 1 calc R . . C21 C 0.15999(12) 0.24822(10) 0.10314(5) 0.1703(8) Uani 1 1 d . . . H21A H 0.1271 0.2605 0.0827 0.255 Uiso 1 1 calc R . . H21B H 0.1226 0.2164 0.1188 0.255 Uiso 1 1 calc R . . H21C H 0.2113 0.2125 0.0978 0.255 Uiso 1 1 calc R . . C22 C 0.51049(8) 0.57229(9) 0.07218(4) 0.0814(5) Uani 1 1 d . . . H22A H 0.4826 0.6208 0.0841 0.122 Uiso 1 1 calc R . . H22B H 0.5560 0.5953 0.0574 0.122 Uiso 1 1 calc R . . H22C H 0.5369 0.5320 0.0883 0.122 Uiso 1 1 calc R . . C23 C 0.29227(9) 0.12000(8) 0.01876(4) 0.0835(5) Uani 1 1 d . . . H23A H 0.3104 0.0867 -0.0009 0.125 Uiso 1 1 calc R . . H23B H 0.2285 0.1177 0.0209 0.125 Uiso 1 1 calc R . . H23C H 0.3192 0.0946 0.0387 0.125 Uiso 1 1 calc R . . O1 O 0.33288(6) 0.18983(6) 0.22382(3) 0.0905(3) Uani 1 1 d . . . O2 O 0.43205(6) 0.52480(5) 0.17877(3) 0.0874(3) Uani 1 1 d . . . O3 O 0.18765(6) 0.32868(6) 0.11789(3) 0.0974(4) Uani 1 1 d . . . O4 O 0.44643(6) 0.52687(6) 0.05293(2) 0.0837(3) Uani 1 1 d . . . O5 O 0.31992(5) 0.20996(5) 0.01526(2) 0.0669(3) Uani 1 1 d . . . C24 C 0.498(2) 0.2463(16) 0.11863(9) 0.1670(3) Uani 0.50 1 d PU A -1 H24A H 0.5314 0.2376 0.1392 0.251 Uiso 0.50 1 calc PR A -1 H24B H 0.4700 0.3039 0.1191 0.251 Uiso 0.50 1 calc PR A -1 H24C H 0.5377 0.2429 0.0995 0.251 Uiso 0.50 1 calc PR A -1 C25 C 0.4363(2) 0.1834(3) 0.11600(10) 0.1286(3) Uani 0.50 1 d PU A -1 N1 N 0.3871(3) 0.1326(2) 0.11546(10) 0.1768(3) Uani 0.50 1 d PU A -1 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0707(10) 0.0860(11) 0.0559(11) 0.000 0.000 -0.0187(10) C2 0.0628(7) 0.0683(7) 0.0586(7) -0.0074(6) 0.0086(6) -0.0171(6) C3 0.0659(7) 0.0705(7) 0.0655(8) -0.0137(6) 0.0046(6) -0.0200(6) C4 0.0741(7) 0.0553(6) 0.0644(8) -0.0090(6) 0.0167(6) -0.0114(6) C5 0.0584(6) 0.0611(7) 0.0625(7) -0.0067(6) 0.0188(6) -0.0021(6) C6 0.0553(7) 0.0735(8) 0.0813(9) -0.0007(7) 0.0087(6) -0.0117(6) C7 0.0614(7) 0.0639(7) 0.0728(9) 0.0024(6) 0.0113(6) -0.0124(6) C8 0.0634(7) 0.0621(7) 0.0854(9) -0.0065(7) 0.0194(7) 0.0089(6) C9 0.0515(6) 0.0507(6) 0.0726(8) 0.0010(6) 0.0087(6) 0.0126(5) C10 0.0659(7) 0.0479(6) 0.0687(8) 0.0037(6) -0.0032(6) -0.0002(6) C11 0.0603(6) 0.0512(6) 0.0603(7) 0.0126(6) -0.0007(6) 0.0016(5) C12 0.0523(3) 0.0429(3) 0.0797(4) -0.0016(3) -0.0032(3) 0.0096(3) C13 0.0532(3) 0.0448(3) 0.0819(4) -0.0044(3) -0.0020(3) 0.0077(3) C14 0.0521(6) 0.0487(6) 0.0926(10) -0.0027(6) 0.0187(6) 0.0064(5) C15 0.0714(7) 0.0504(6) 0.0650(8) 0.0058(6) -0.0079(6) 0.0088(6) C16 0.0682(7) 0.0447(6) 0.0416(6) 0.0025(5) -0.0046(6) 0.0085(5) C17 0.0715(7) 0.0432(5) 0.0496(7) 0.0048(5) -0.0011(6) 0.0045(5) C18 0.0597(6) 0.0478(6) 0.0456(6) -0.0025(5) -0.0029(5) 0.0038(5) C19 0.0942(9) 0.0844(9) 0.1480(15) 0.0206(10) -0.0259(10) -0.0425(8) C20 0.1124(10) 0.1124(10) 0.0921(11) 0.0099(9) -0.0067(9) -0.0577(8) C21 0.1876(14) 0.0878(9) 0.2355(19) -0.0629(11) 0.1192(13) -0.0728(10) C22 0.0718(8) 0.0973(9) 0.0750(10) 0.0020(8) -0.0002(7) -0.0156(7) C23 0.0756(8) 0.0627(7) 0.1122(12) 0.0151(8) 0.0039(8) -0.0103(7) O1 0.0809(5) 0.0778(5) 0.1127(8) 0.0243(5) -0.0129(5) -0.0322(5) O2 0.0953(6) 0.0619(5) 0.1050(7) 0.0041(5) 0.0005(6) -0.0241(5) O3 0.0828(5) 0.0725(5) 0.1370(8) -0.0226(6) 0.0477(5) -0.0204(5) O4 0.1005(6) 0.0911(6) 0.0594(6) 0.0096(5) -0.0020(5) -0.0400(5) O5 0.0656(5) 0.0522(4) 0.0830(6) -0.0017(4) -0.0060(4) 0.0005(4) C24 0.1670(5) 0.1668(5) 0.1673(5) 0.0000(4) 0.0000(4) -0.0008(4) C25 0.1285(5) 0.1286(5) 0.1285(5) 0.0001(4) -0.0002(4) 0.0002(4) N1 0.1768(5) 0.1766(5) 0.1771(5) 0.0000(4) -0.0004(4) -0.0008(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 C1 C2 1.5123(16) 6_554 ? C1 C2 1.5123(15) . ? C1 H1A 0.9700 . ? C1 H1B 0.9700 . ? C2 C7 1.3867(16) . ? C2 C3 1.3883(16) . ? C3 C4 1.3765(17) . ? C3 H3 0.9300 . ? C4 C5 1.3811(16) . ? C4 O2 1.3862(14) . ? C5 C6 1.3941(16) . ? C5 C8 1.5084(17) . ? C6 C7 1.3836(17) . ? C6 H6 0.9300 . ? C7 O1 1.3792(14) . ? C8 C9 1.5052(17) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 C10 1.3845(15) . ? C9 C14 1.3881(16) . ? C10 C11 1.3802(17) . ? C10 H10 0.9300 . ? C11 O4 1.3828(14) . ? C11 C12 1.3873(15) . ? C12 C13 1.3863(15) . ? C12 C15 1.5061(17) . ? C13 C14 1.3705(18) . ? C13 H13 0.9300 . ? C14 O3 1.3795(14) . ? C15 C16 1.5125(15) . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C16 C17 1.3803(15) . ? C16 C18 1.3930(14) . ? C17 C18 1.3826(15) 6_554 ? C17 H17 0.9300 . ? C18 C17 1.3826(15) 6_554 ? C18 O5 1.3829(13) . ? C19 O1 1.4193(16) . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 0.9600 . ? C20 O2 1.4092(16) . ? C20 H20A 0.9600 . ? C20 H20B 0.9600 . ? C20 H20C 0.9600 . ? C21 O3 1.3999(18) . ? C21 H21A 0.9600 . ? C21 H21B 0.9600 . ? C21 H21C 0.9600 . ? C22 O4 1.3984(15) . ? C22 H22A 0.9600 . ? C22 H22B 0.9600 . ? C22 H22C 0.9600 . ? C23 O5 1.4161(14) . ? C23 H23A 0.9600 . ? C23 H23B 0.9600 . ? C23 H23C 0.9600 . ? C24 C25 1.32(3) . ? C24 H24A 0.9600 . ? C24 H24B 0.9600 . ? C24 H24C 0.9600 . ? C25 N1 1.059(5) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 C2 111.75(14) 6_554 . ? C2 C1 H1A 109.3 6_554 . ? C2 C1 H1A 109.3 . . ? C2 C1 H1B 109.3 6_554 . ? C2 C1 H1B 109.3 . . ? H1A C1 H1B 107.9 . . ? C7 C2 C3 117.87(11) . . ? C7 C2 C1 121.12(10) . . ? C3 C2 C1 120.99(9) . . ? C4 C3 C2 121.64(11) . . ? C4 C3 H3 119.2 . . ? C2 C3 H3 119.2 . . ? C3 C4 C5 120.95(11) . . ? C3 C4 O2 123.31(11) . . ? C5 C4 O2 115.74(10) . . ? C4 C5 C6 117.55(11) . . ? C4 C5 C8 121.45(10) . . ? C6 C5 C8 120.96(10) . . ? C7 C6 C5 121.64(11) . . ? C7 C6 H6 119.2 . . ? C5 C6 H6 119.2 . . ? O1 C7 C6 123.55(11) . . ? O1 C7 C2 116.12(11) . . ? C6 C7 C2 120.32(11) . . ? C9 C8 C5 112.54(9) . . ? C9 C8 H8A 109.1 . . ? C5 C8 H8A 109.1 . . ? C9 C8 H8B 109.1 . . ? C5 C8 H8B 109.1 . . ? H8A C8 H8B 107.8 . . ? C10 C9 C14 117.41(11) . . ? C10 C9 C8 121.27(10) . . ? C14 C9 C8 121.28(10) . . ? C11 C10 C9 121.64(10) . . ? C11 C10 H10 119.2 . . ? C9 C10 H10 119.2 . . ? C10 C11 O4 123.27(10) . . ? C10 C11 C12 120.80(10) . . ? O4 C11 C12 115.92(10) . . ? C13 C12 C11 117.22(11) . . ? C13 C12 C15 120.43(10) . . ? C11 C12 C15 122.25(10) . . ? C14 C13 C12 122.01(11) . . ? C14 C13 H13 119.0 . . ? C12 C13 H13 119.0 . . ? C13 C14 O3 123.14(10) . . ? C13 C14 C9 120.84(10) . . ? O3 C14 C9 116.00(11) . . ? C12 C15 C16 110.96(9) . . ? C12 C15 H15A 109.4 . . ? C16 C15 H15A 109.4 . . ? C12 C15 H15B 109.4 . . ? C16 C15 H15B 109.4 . . ? H15A C15 H15B 108.0 . . ? C17 C16 C18 117.95(10) . . ? C17 C16 C15 120.40(9) . . ? C18 C16 C15 121.62(10) . . ? C16 C17 C18 121.76(10) . 6_554 ? C16 C17 H17 119.1 . . ? C18 C17 H17 119.1 6_554 . ? C17 C18 O5 123.60(9) 6_554 . ? C17 C18 C16 120.26(10) 6_554 . ? O5 C18 C16 116.13(9) . . ? O1 C19 H19A 109.5 . . ? O1 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? O1 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? O2 C20 H20A 109.5 . . ? O2 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? O2 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? O3 C21 H21A 109.5 . . ? O3 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? O3 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? O4 C22 H22A 109.5 . . ? O4 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? O4 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? O5 C23 H23A 109.5 . . ? O5 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? O5 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? C7 O1 C19 118.28(10) . . ? C4 O2 C20 118.08(10) . . ? C14 O3 C21 117.70(12) . . ? C11 O4 C22 118.55(10) . . ? C18 O5 C23 118.05(8) . . ? N1 C25 C24 176.6(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 C2 C1 C2 C7 89.66(11) 6_554 . . . ? C2 C1 C2 C3 -88.45(11) 6_554 . . . ? C7 C2 C3 C4 -1.65(18) . . . . ? C1 C2 C3 C4 176.52(12) . . . . ? C2 C3 C4 C5 1.94(19) . . . . ? C2 C3 C4 O2 -179.24(11) . . . . ? C3 C4 C5 C6 -0.45(18) . . . . ? O2 C4 C5 C6 -179.35(11) . . . . ? C3 C4 C5 C8 -178.19(11) . . . . ? O2 C4 C5 C8 2.91(17) . . . . ? C4 C5 C6 C7 -1.28(18) . . . . ? C8 C5 C6 C7 176.47(11) . . . . ? C5 C6 C7 O1 -179.43(11) . . . . ? C5 C6 C7 C2 1.55(19) . . . . ? C3 C2 C7 O1 -179.17(11) . . . . ? C1 C2 C7 O1 2.66(17) . . . . ? C3 C2 C7 C6 -0.08(18) . . . . ? C1 C2 C7 C6 -178.25(12) . . . . ? C4 C5 C8 C9 85.11(14) . . . . ? C6 C5 C8 C9 -92.55(13) . . . . ? C5 C8 C9 C10 -87.77(13) . . . . ? C5 C8 C9 C14 89.77(13) . . . . ? C14 C9 C10 C11 -0.81(16) . . . . ? C8 C9 C10 C11 176.83(10) . . . . ? C9 C10 C11 O4 -178.78(10) . . . . ? C9 C10 C11 C12 2.65(17) . . . . ? C10 C11 C12 C13 -1.86(16) . . . . ? O4 C11 C12 C13 179.48(9) . . . . ? C10 C11 C12 C15 -178.30(10) . . . . ? O4 C11 C12 C15 3.03(15) . . . . ? C11 C12 C13 C14 -0.70(16) . . . . ? C15 C12 C13 C14 175.82(10) . . . . ? C12 C13 C14 O3 -178.63(10) . . . . ? C12 C13 C14 C9 2.54(17) . . . . ? C10 C9 C14 C13 -1.74(16) . . . . ? C8 C9 C14 C13 -179.38(10) . . . . ? C10 C9 C14 O3 179.35(10) . . . . ? C8 C9 C14 O3 1.71(15) . . . . ? C13 C12 C15 C16 -84.49(13) . . . . ? C11 C12 C15 C16 91.85(12) . . . . ? C12 C15 C16 C17 -92.09(12) . . . . ? C12 C15 C16 C18 85.88(12) . . . . ? C18 C16 C17 C18 0.00(14) . . . 6_554 ? C15 C16 C17 C18 178.05(10) . . . 6_554 ? C17 C16 C18 C17 -1.67(14) . . . 6_554 ? C15 C16 C18 C17 -179.69(10) . . . 6_554 ? C17 C16 C18 O5 179.34(10) . . . . ? C15 C16 C18 O5 1.32(15) . . . . ? C6 C7 O1 C19 9.74(18) . . . . ? C2 C7 O1 C19 -171.21(12) . . . . ? C3 C4 O2 C20 23.01(18) . . . . ? C5 C4 O2 C20 -158.11(12) . . . . ? C13 C14 O3 C21 15.16(17) . . . . ? C9 C14 O3 C21 -165.96(12) . . . . ? C10 C11 O4 C22 22.17(16) . . . . ? C12 C11 O4 C22 -159.20(10) . . . . ? C17 C18 O5 C23 6.54(16) 6_554 . . . ? C16 C18 O5 C23 -174.51(11) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.163 _refine_diff_density_min -0.138 _refine_diff_density_rms 0.032 _database_code_depnum_ccdc_archive 'CCDC 968773' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_tll18-3 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C45 H50 O10, C H2 Cl2' _chemical_formula_sum 'C46 H52 Cl2 O10' _chemical_formula_weight 835.78 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' Cl Cl 0.1484 0.1585 '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 tetragonal _symmetry_space_group_name_H-M 'I 4(1)/a' _symmetry_space_group_name_HALL '-I 4ad' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-y+3/4, x+1/4, z+1/4' 'y+3/4, -x+3/4, z+3/4' 'x+1/2, y+1/2, z+1/2' '-x+1, -y+1/2, z+1' '-y+5/4, x+3/4, z+3/4' 'y+5/4, -x+5/4, z+5/4' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'y-3/4, -x-1/4, -z-1/4' '-y-3/4, x-3/4, -z-3/4' '-x+1/2, -y+1/2, -z+1/2' 'x, y+1/2, -z' 'y-1/4, -x+1/4, -z+1/4' '-y-1/4, x-1/4, -z-1/4' _cell_length_a 14.928(4) _cell_length_b 14.928(4) _cell_length_c 39.286(10) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 8754(4) _cell_formula_units_Z 8 _cell_measurement_temperature 153(2) _cell_measurement_reflns_used 26715 _cell_measurement_theta_min 3.10 _cell_measurement_theta_max 27.45 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.36 _exptl_crystal_size_min 0.28 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.268 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 3536 _exptl_absorpt_coefficient_mu 0.205 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9256 _exptl_absorpt_correction_T_max 0.9447 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 153(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 41658 _diffrn_reflns_av_R_equivalents 0.0480 _diffrn_reflns_av_sigmaI/netI 0.0274 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -50 _diffrn_reflns_limit_l_max 50 _diffrn_reflns_theta_min 3.10 _diffrn_reflns_theta_max 27.45 _reflns_number_total 4991 _reflns_number_gt 3413 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0591P)^2^+3.9339P] 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 4991 _refine_ls_number_parameters 299 _refine_ls_number_restraints 20 _refine_ls_R_factor_all 0.0784 _refine_ls_R_factor_gt 0.0519 _refine_ls_wR_factor_ref 0.1398 _refine_ls_wR_factor_gt 0.1271 _refine_ls_goodness_of_fit_ref 1.065 _refine_ls_restrained_S_all 1.088 _refine_ls_shift/su_max 0.039 _refine_ls_shift/su_mean 0.002 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.0000 0.7500 0.24457(3) 0.0535(3) Uani 1 2 d S . . H1A H 0.0361 0.7104 0.2594 0.064 Uiso 0.50 1 calc PR . . H1B H -0.0361 0.7896 0.2594 0.064 Uiso 0.50 1 calc PR . . C2 C 0.06215(5) 0.80672(5) 0.222969(18) 0.04697(19) Uani 1 1 d . . . C3 C 0.03661(5) 0.89149(5) 0.211865(18) 0.0510(2) Uani 1 1 d . . . H3 H -0.0193 0.9153 0.2191 0.061 Uiso 1 1 calc R . . C4 C 0.09055(5) 0.94199(5) 0.190638(18) 0.0486(2) Uani 1 1 d . . . C5 C 0.17377(5) 0.91045(5) 0.180406(18) 0.04699(19) Uani 1 1 d . . . C6 C 0.20064(5) 0.82603(5) 0.19195(2) 0.0512(2) Uani 1 1 d . . . H6 H 0.2578 0.8036 0.1856 0.061 Uiso 1 1 calc R . . C7 C 0.14545(5) 0.77423(5) 0.212528(19) 0.0498(2) Uani 1 1 d . . . C8 C 0.23246(5) 0.96411(5) 0.15631(2) 0.0531(2) Uani 1 1 d . . . H8A H 0.2255 1.0287 0.1614 0.064 Uiso 1 1 calc R . . H8B H 0.2960 0.9479 0.1602 0.064 Uiso 1 1 calc R . . C9 C 0.20909(5) 0.94759(4) 0.119353(19) 0.04532(19) Uani 1 1 d U . . C10 C 0.14364(5) 0.99830(5) 0.103128(18) 0.0458(2) Uani 1 1 d . . . H10 H 0.1153 1.0456 0.1152 0.055 Uiso 1 1 calc R . . C11 C 0.11873(5) 0.98133(4) 0.069672(18) 0.04378(19) Uani 1 1 d . . . C12 C 0.16134(4) 0.91471(4) 0.050907(18) 0.04185(18) Uani 1 1 d . . . C13 C 0.22754(5) 0.86508(5) 0.06691(2) 0.0480(2) Uani 1 1 d . . . H13 H 0.2583 0.8201 0.0544 0.058 Uiso 1 1 calc R . . C14 C 0.24998(5) 0.87969(5) 0.10077(2) 0.0497(2) Uani 1 1 d U . . C15 C 0.13445(5) 0.89219(5) 0.014736(18) 0.04634(19) Uani 1 1 d . . . H15A H 0.1881 0.8733 0.0017 0.056 Uiso 1 1 calc R . . H15B H 0.1094 0.9462 0.0036 0.056 Uiso 1 1 calc R . . C16 C 0.06535(5) 0.81775(4) 0.014044(16) 0.03980(17) Uani 1 1 d . . . C17 C 0.09013(5) 0.72804(4) 0.014455(16) 0.04044(17) Uani 1 1 d . . . C18 C -0.02525(5) 0.83874(4) 0.014018(16) 0.04140(18) Uani 1 1 d . . . H18 H -0.0432 0.8998 0.0137 0.050 Uiso 1 1 calc R . . C19 C -0.02452(6) 1.04825(6) 0.17765(2) 0.0768(3) Uani 1 1 d . . . H19A H -0.0581 0.9986 0.1675 0.115 Uiso 1 1 calc R . . H19B H -0.0329 1.1023 0.1639 0.115 Uiso 1 1 calc R . . H19C H -0.0463 1.0592 0.2008 0.115 Uiso 1 1 calc R . . C20 C 0.24569(6) 0.64916(6) 0.21046(3) 0.0765(3) Uani 1 1 d . . . H20A H 0.2387 0.6427 0.1858 0.115 Uiso 1 1 calc R . . H20B H 0.2539 0.5900 0.2208 0.115 Uiso 1 1 calc R . . H20C H 0.2982 0.6865 0.2153 0.115 Uiso 1 1 calc R . . C21 C -0.01196(5) 1.07364(6) 0.07244(2) 0.0603(2) Uani 1 1 d U . . H21A H -0.0384 1.0323 0.0890 0.090 Uiso 1 1 calc R . . H21B H -0.0590 1.0968 0.0574 0.090 Uiso 1 1 calc R . . H21C H 0.0166 1.1235 0.0845 0.090 Uiso 1 1 calc R . . C22 C 0.34193(8) 0.74951(7) 0.10237(4) 0.1359(4) Uani 1 1 d . . . H22A H 0.2899 0.7120 0.0971 0.204 Uiso 1 1 calc R . . H22B H 0.3818 0.7172 0.1179 0.204 Uiso 1 1 calc R . . H22C H 0.3742 0.7637 0.0813 0.204 Uiso 1 1 calc R . . C23 C 0.20911(6) 0.62032(5) 0.01826(2) 0.0610(3) Uani 1 1 d . . . H23A H 0.1829 0.5944 0.0389 0.091 Uiso 1 1 calc R . . H23B H 0.2746 0.6179 0.0198 0.091 Uiso 1 1 calc R . . H23C H 0.1891 0.5862 -0.0016 0.091 Uiso 1 1 calc R . . C25 C 0.03580(12) 0.74608(15) 0.13424(6) 0.0639(8) Uani 0.25 1 d PDU . 1 H25A H 0.0543 0.7478 0.1584 0.077 Uiso 0.25 1 calc PR . 1 H25B H 0.0601 0.8012 0.1237 0.077 Uiso 0.25 1 calc PR . 1 Cl1 Cl 0.09237(6) 0.66083(5) 0.11672(2) 0.1407(4) Uani 0.25 1 d PD A 1 Cl3 Cl -0.05645(9) 0.76963(15) 0.11072(6) 0.2118(11) Uani 0.25 1 d PD . 2 C26 C 0.00256(15) 0.71499(12) 0.10155(6) 0.0669(8) Uani 0.25 1 d PDU . 3 H26A H -0.0552 0.6890 0.0941 0.080 Uiso 0.25 1 calc PR . 3 H26B H 0.0491 0.6966 0.0850 0.080 Uiso 0.25 1 calc PR . 3 Cl2 Cl -0.01793(16) 0.80911(9) 0.12421(6) 0.2225(12) Uani 0.25 1 d PD . 3 Cl4 Cl 0.09237(6) 0.66083(5) 0.11672(2) 0.1407(4) Uani 0.25 1 d P B 4 O1 O 0.06737(4) 1.02618(4) 0.178737(15) 0.06553(18) Uani 1 1 d . . . O2 O 0.16816(4) 0.69012(4) 0.224242(16) 0.06651(18) Uani 1 1 d . . . O3 O 0.05223(4) 1.02836(4) 0.053015(13) 0.06489(17) Uani 1 1 d U . . O4 O 0.31302(4) 0.82921(4) 0.117857(17) 0.07502(19) Uani 1 1 d . . . O5 O 0.18124(3) 0.71056(3) 0.014995(14) 0.04987(14) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0549(6) 0.0626(6) 0.0431(5) 0.000 0.000 0.0152(5) C2 0.0479(4) 0.0511(4) 0.0419(3) -0.0073(3) -0.0073(3) 0.0106(3) C3 0.0521(4) 0.0542(4) 0.0466(4) -0.0109(3) -0.0055(3) 0.0168(3) C4 0.0568(4) 0.0405(3) 0.0484(4) -0.0094(3) -0.0127(3) 0.0105(3) C5 0.0456(3) 0.0441(4) 0.0513(4) -0.0093(3) -0.0164(3) 0.0013(3) C6 0.0401(3) 0.0530(4) 0.0604(4) -0.0043(4) -0.0103(3) 0.0096(3) C7 0.0500(4) 0.0479(4) 0.0515(4) -0.0016(3) -0.0091(3) 0.0121(3) C8 0.0472(4) 0.0437(4) 0.0686(4) -0.0052(4) -0.0178(3) -0.0061(3) C9 0.0390(3) 0.0358(3) 0.0611(4) 0.0005(3) -0.0053(3) -0.0099(3) C10 0.0474(4) 0.0383(3) 0.0518(4) 0.0023(3) 0.0028(3) -0.0007(3) C11 0.0452(3) 0.0385(3) 0.0476(4) 0.0090(3) 0.0043(3) 0.0010(3) C12 0.0400(3) 0.0322(3) 0.0533(4) 0.0048(3) 0.0056(3) -0.0099(3) C13 0.0394(3) 0.0354(3) 0.0692(4) -0.0067(3) -0.0004(3) -0.0066(3) C14 0.0362(3) 0.0364(3) 0.0766(5) -0.0002(3) -0.0134(3) -0.0051(3) C15 0.0549(4) 0.0365(3) 0.0477(4) 0.0058(3) 0.0104(3) -0.0063(3) C16 0.0533(4) 0.0333(3) 0.0328(3) 0.0032(3) 0.0044(3) -0.0048(3) C17 0.0479(3) 0.0381(3) 0.0352(3) -0.0012(3) 0.0023(3) -0.0014(3) C18 0.0561(4) 0.0313(3) 0.0369(3) 0.0034(3) 0.0011(3) -0.0010(3) C19 0.0837(5) 0.0806(5) 0.0659(5) 0.0113(4) 0.0033(5) 0.0420(4) C20 0.0698(5) 0.0632(5) 0.0964(6) 0.0144(5) 0.0161(5) 0.0321(4) C21 0.0480(4) 0.0739(5) 0.0589(4) 0.0012(4) -0.0031(4) 0.0125(4) C22 0.1479(8) 0.0665(5) 0.1933(10) -0.0540(6) -0.1025(7) 0.0574(5) C23 0.0563(4) 0.0467(4) 0.0799(5) 0.0103(4) -0.0025(4) 0.0046(4) C25 0.0745(16) 0.0720(15) 0.0452(12) -0.0088(13) -0.0195(11) -0.0200(15) Cl1 0.1628(7) 0.1215(6) 0.1379(6) -0.0095(5) 0.0083(6) -0.0122(5) Cl3 0.1244(10) 0.259(3) 0.252(2) 0.001(2) -0.0934(11) -0.0345(14) C26 0.0830(16) 0.0781(16) 0.0396(12) -0.0187(11) -0.0067(13) -0.0325(15) Cl2 0.273(3) 0.1309(11) 0.263(2) -0.0932(12) -0.017(2) -0.0508(15) Cl4 0.1628(7) 0.1215(6) 0.1379(6) -0.0095(5) 0.0083(6) -0.0122(5) O1 0.0710(3) 0.0482(3) 0.0774(4) 0.0017(3) -0.0037(3) 0.0196(3) O2 0.0581(3) 0.0582(3) 0.0832(4) 0.0159(3) 0.0095(3) 0.0243(3) O3 0.0790(3) 0.0696(3) 0.0461(3) 0.0084(3) 0.0010(3) 0.0338(3) O4 0.0641(3) 0.0535(3) 0.1075(4) -0.0170(3) -0.0403(3) 0.0163(3) O5 0.0488(3) 0.0388(2) 0.0620(3) -0.0027(2) 0.0051(2) -0.0005(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 C1 C2 1.5158(10) 6_464 ? C1 C2 1.5158(10) . ? C1 H1A 0.9900 . ? C1 H1B 0.9900 . ? C2 C3 1.3918(11) . ? C2 C7 1.3963(11) . ? C3 C4 1.3828(11) . ? C3 H3 0.9500 . ? C4 O1 1.3848(10) . ? C4 C5 1.3881(11) . ? C5 C6 1.3980(11) . ? C5 C8 1.5183(11) . ? C6 C7 1.3895(11) . ? C6 H6 0.9500 . ? C7 O2 1.3796(10) . ? C8 C9 1.5134(11) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 C14 1.3903(10) . ? C9 C10 1.3906(10) . ? C10 C11 1.3892(11) . ? C10 H10 0.9500 . ? C11 O3 1.3808(9) . ? C11 C12 1.3918(10) . ? C12 C13 1.3860(10) . ? C12 C15 1.5144(10) . ? C13 C14 1.3888(12) . ? C13 H13 0.9500 . ? C14 O4 1.3799(10) . ? C15 C16 1.5164(10) . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C16 C18 1.3882(11) . ? C16 C17 1.3894(10) . ? C17 O5 1.3851(9) . ? C17 C18 1.3900(10) 6_464 ? C18 C17 1.3900(10) 6_464 ? C18 H18 0.9500 . ? C19 O1 1.4115(12) . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? C20 O2 1.4164(11) . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C20 H20C 0.9800 . ? C21 O3 1.3990(10) . ? C21 H21A 0.9800 . ? C21 H21B 0.9800 . ? C21 H21C 0.9800 . ? C22 O4 1.4042(13) . ? C22 H22A 0.9800 . ? C22 H22B 0.9800 . ? C22 H22C 0.9800 . ? C23 O5 1.4157(10) . ? C23 H23A 0.9800 . ? C23 H23B 0.9800 . ? C23 H23C 0.9800 . ? C25 C25 1.075(4) 6_464 ? C25 Cl1 1.675(2) . ? C25 H25A 0.9900 . ? C25 H25B 0.9900 . ? Cl3 Cl3 1.784(3) 6_464 ? C26 Cl2 0.987(3) 6_464 ? C26 C26 1.048(4) 6_464 ? C26 Cl2 1.691(2) . ? C26 H26A 0.9900 . ? C26 H26B 0.9900 . ? Cl2 C26 0.987(3) 6_464 ? Cl2 Cl2 1.844(3) 6_464 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 C2 111.92(9) 6_464 . ? C2 C1 H1A 109.2 6_464 . ? C2 C1 H1A 109.2 . . ? C2 C1 H1B 109.2 6_464 . ? C2 C1 H1B 109.2 . . ? H1A C1 H1B 107.9 . . ? C3 C2 C7 117.89(7) . . ? C3 C2 C1 121.04(6) . . ? C7 C2 C1 121.03(6) . . ? C4 C3 C2 121.68(7) . . ? C4 C3 H3 119.2 . . ? C2 C3 H3 119.2 . . ? C3 C4 O1 123.57(7) . . ? C3 C4 C5 120.72(7) . . ? O1 C4 C5 115.70(7) . . ? C4 C5 C6 117.94(7) . . ? C4 C5 C8 121.20(6) . . ? C6 C5 C8 120.81(6) . . ? C7 C6 C5 121.35(7) . . ? C7 C6 H6 119.3 . . ? C5 C6 H6 119.3 . . ? O2 C7 C6 123.71(7) . . ? O2 C7 C2 115.91(7) . . ? C6 C7 C2 120.38(7) . . ? C9 C8 C5 112.29(6) . . ? C9 C8 H8A 109.1 . . ? C5 C8 H8A 109.1 . . ? C9 C8 H8B 109.1 . . ? C5 C8 H8B 109.1 . . ? H8A C8 H8B 107.9 . . ? C14 C9 C10 117.69(7) . . ? C14 C9 C8 121.43(7) . . ? C10 C9 C8 120.86(6) . . ? C11 C10 C9 121.49(7) . . ? C11 C10 H10 119.3 . . ? C9 C10 H10 119.3 . . ? O3 C11 C10 123.24(6) . . ? O3 C11 C12 116.16(6) . . ? C10 C11 C12 120.60(6) . . ? C13 C12 C11 117.87(7) . . ? C13 C12 C15 119.74(6) . . ? C11 C12 C15 122.31(6) . . ? C12 C13 C14 121.50(7) . . ? C12 C13 H13 119.2 . . ? C14 C13 H13 119.2 . . ? O4 C14 C13 123.00(7) . . ? O4 C14 C9 116.24(7) . . ? C13 C14 C9 120.76(7) . . ? C12 C15 C16 111.09(6) . . ? C12 C15 H15A 109.4 . . ? C16 C15 H15A 109.4 . . ? C12 C15 H15B 109.4 . . ? C16 C15 H15B 109.4 . . ? H15A C15 H15B 108.0 . . ? C18 C16 C17 118.48(6) . . ? C18 C16 C15 119.82(6) . . ? C17 C16 C15 121.67(6) . . ? O5 C17 C16 116.30(6) . . ? O5 C17 C18 123.32(6) . 6_464 ? C16 C17 C18 120.37(6) . 6_464 ? C16 C18 C17 121.13(6) . 6_464 ? C16 C18 H18 119.4 . . ? C17 C18 H18 119.4 6_464 . ? O1 C19 H19A 109.5 . . ? O1 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? O1 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? O2 C20 H20A 109.5 . . ? O2 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? O2 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? O3 C21 H21A 109.5 . . ? O3 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? O3 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? O4 C22 H22A 109.5 . . ? O4 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? O4 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? O5 C23 H23A 109.5 . . ? O5 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? O5 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? C25 C25 Cl1 125.7(3) 6_464 . ? C25 C25 H25A 105.9 6_464 . ? Cl1 C25 H25A 105.9 . . ? C25 C25 H25B 105.9 6_464 . ? Cl1 C25 H25B 105.9 . . ? H25A C25 H25B 106.2 . . ? Cl2 C26 C26 112.36(16) 6_464 6_464 ? Cl2 C26 Cl2 82.5(2) 6_464 . ? C26 C26 Cl2 32.67(11) 6_464 . ? Cl2 C26 H26A 109.1 6_464 . ? C26 C26 H26A 109.1 6_464 . ? Cl2 C26 H26A 109.0 . . ? Cl2 C26 H26B 109.1 6_464 . ? C26 C26 H26B 109.1 6_464 . ? Cl2 C26 H26B 134.6 . . ? H26A C26 H26B 107.9 . . ? C26 Cl2 C26 34.97(15) 6_464 . ? C26 Cl2 Cl2 65.40(15) 6_464 6_464 ? C26 Cl2 Cl2 32.05(10) . 6_464 ? C4 O1 C19 117.70(7) . . ? C7 O2 C20 117.78(7) . . ? C11 O3 C21 118.66(6) . . ? C14 O4 C22 117.49(8) . . ? C17 O5 C23 117.98(6) . . ? 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 C2 C1 C2 C3 88.00(7) 6_464 . . . ? C2 C1 C2 C7 -89.58(7) 6_464 . . . ? C7 C2 C3 C4 1.22(11) . . . . ? C1 C2 C3 C4 -176.44(7) . . . . ? C2 C3 C4 O1 179.36(7) . . . . ? C2 C3 C4 C5 -1.83(11) . . . . ? C3 C4 C5 C6 0.62(11) . . . . ? O1 C4 C5 C6 179.53(6) . . . . ? C3 C4 C5 C8 178.25(7) . . . . ? O1 C4 C5 C8 -2.85(10) . . . . ? C4 C5 C6 C7 1.14(11) . . . . ? C8 C5 C6 C7 -176.50(7) . . . . ? C5 C6 C7 O2 179.13(7) . . . . ? C5 C6 C7 C2 -1.74(11) . . . . ? C3 C2 C7 O2 179.75(7) . . . . ? C1 C2 C7 O2 -2.60(10) . . . . ? C3 C2 C7 C6 0.55(11) . . . . ? C1 C2 C7 C6 178.20(7) . . . . ? C4 C5 C8 C9 -84.95(8) . . . . ? C6 C5 C8 C9 92.60(8) . . . . ? C5 C8 C9 C14 -89.88(8) . . . . ? C5 C8 C9 C10 88.06(8) . . . . ? C14 C9 C10 C11 0.86(10) . . . . ? C8 C9 C10 C11 -177.15(7) . . . . ? C9 C10 C11 O3 177.99(7) . . . . ? C9 C10 C11 C12 -2.44(11) . . . . ? O3 C11 C12 C13 -179.02(6) . . . . ? C10 C11 C12 C13 1.37(10) . . . . ? O3 C11 C12 C15 -2.24(10) . . . . ? C10 C11 C12 C15 178.16(6) . . . . ? C11 C12 C13 C14 1.20(10) . . . . ? C15 C12 C13 C14 -175.67(6) . . . . ? C12 C13 C14 O4 177.38(6) . . . . ? C12 C13 C14 C9 -2.79(11) . . . . ? C10 C9 C14 O4 -178.46(6) . . . . ? C8 C9 C14 O4 -0.45(10) . . . . ? C10 C9 C14 C13 1.71(10) . . . . ? C8 C9 C14 C13 179.71(7) . . . . ? C13 C12 C15 C16 84.54(8) . . . . ? C11 C12 C15 C16 -92.18(8) . . . . ? C12 C15 C16 C18 92.11(7) . . . . ? C12 C15 C16 C17 -85.93(8) . . . . ? C18 C16 C17 O5 -179.04(6) . . . . ? C15 C16 C17 O5 -0.97(9) . . . . ? C18 C16 C17 C18 1.52(8) . . . 6_464 ? C15 C16 C17 C18 179.59(6) . . . 6_464 ? C17 C16 C18 C17 0.12(9) . . . 6_464 ? C15 C16 C18 C17 -177.99(6) . . . 6_464 ? Cl2 C26 Cl2 C26 156.2(5) 6_464 . . 6_464 ? C26 C26 Cl2 Cl2 -156.2(5) 6_464 . . 6_464 ? C3 C4 O1 C19 -23.32(11) . . . . ? C5 C4 O1 C19 157.81(7) . . . . ? C6 C7 O2 C20 -9.75(11) . . . . ? C2 C7 O2 C20 171.08(7) . . . . ? C10 C11 O3 C21 -21.33(10) . . . . ? C12 C11 O3 C21 159.08(7) . . . . ? C13 C14 O4 C22 -12.92(11) . . . . ? C9 C14 O4 C22 167.25(8) . . . . ? C16 C17 O5 C23 174.89(6) . . . . ? C18 C17 O5 C23 -5.69(10) 6_464 . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.45 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.373 _refine_diff_density_min -0.338 _refine_diff_density_rms 0.034 _database_code_depnum_ccdc_archive 'CCDC 968774' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_tll-d _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C45 H50 O10, C4 H8 O2' _chemical_formula_sum 'C49 H58 O12' _chemical_formula_weight 838.95 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 tetragonal _symmetry_space_group_name_H-M I4(1)/a _symmetry_space_group_name_HALL '-I 4ad' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-y+3/4, x+1/4, z+1/4' 'y+3/4, -x+3/4, z+3/4' 'x+1/2, y+1/2, z+1/2' '-x+1, -y+1/2, z+1' '-y+5/4, x+3/4, z+3/4' 'y+5/4, -x+5/4, z+5/4' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'y-3/4, -x-1/4, -z-1/4' '-y-3/4, x-3/4, -z-3/4' '-x+1/2, -y+1/2, -z+1/2' 'x, y+1/2, -z' 'y-1/4, -x+1/4, -z+1/4' '-y-1/4, x-1/4, -z-1/4' _cell_length_a 15.030(2) _cell_length_b 15.030(2) _cell_length_c 40.076(8) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 9053(3) _cell_formula_units_Z 8 _cell_measurement_temperature 291(2) _cell_measurement_reflns_used 21944 _cell_measurement_theta_min 3.05 _cell_measurement_theta_max 27.46 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.54 _exptl_crystal_size_mid 0.51 _exptl_crystal_size_min 0.38 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.231 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 3584 _exptl_absorpt_coefficient_mu 0.087 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9541 _exptl_absorpt_correction_T_max 0.9672 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 291(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 'Rigaku RAXIS-RAPID' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 42013 _diffrn_reflns_av_R_equivalents 0.0483 _diffrn_reflns_av_sigmaI/netI 0.0312 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -51 _diffrn_reflns_limit_l_max 51 _diffrn_reflns_theta_min 3.07 _diffrn_reflns_theta_max 27.47 _reflns_number_total 5178 _reflns_number_gt 2798 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'RAPID-AUTO (Rigaku Corporation, 1998)' _computing_cell_refinement RAPID-AUTO _computing_data_reduction 'CrystalStructure (Rigaku/MSC and Rigaku Corporation, 2002)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 2008)' _computing_publication_material SHELXL-97 _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^)+(0.0929P)^2^+3.2084P] 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 5178 _refine_ls_number_parameters 290 _refine_ls_number_restraints 13 _refine_ls_R_factor_all 0.1173 _refine_ls_R_factor_gt 0.0666 _refine_ls_wR_factor_ref 0.2071 _refine_ls_wR_factor_gt 0.1788 _refine_ls_goodness_of_fit_ref 1.064 _refine_ls_restrained_S_all 1.066 _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 C1 C 1.08954(17) 0.72768(15) 0.01429(5) 0.0592(6) Uani 1 1 d . . . C2 C 1.02486(17) 0.66193(15) 0.01366(5) 0.0609(6) Uani 1 1 d . . . H2 H 1.0421 0.6025 0.0131 0.073 Uiso 1 1 calc R . . C3 C 0.93495(17) 0.68287(14) 0.01386(5) 0.0582(6) Uani 1 1 d . . . C4 C 0.86596(18) 0.60946(16) 0.01466(6) 0.0665(6) Uani 1 1 d . . . H4A H 0.8902 0.5565 0.0042 0.080 Uiso 1 1 calc R . . H4B H 0.8141 0.6278 0.0020 0.080 Uiso 1 1 calc R . . C5 C 0.83834(16) 0.58778(14) 0.05009(6) 0.0591(6) Uani 1 1 d . . . C6 C 0.88118(16) 0.52311(16) 0.06902(6) 0.0637(6) Uani 1 1 d . . . C7 C 0.85611(16) 0.50745(16) 0.10200(6) 0.0655(6) Uani 1 1 d . . . H7 H 0.8842 0.4625 0.1140 0.079 Uiso 1 1 calc R . . C8 C 0.79023(16) 0.55738(16) 0.11736(6) 0.0633(6) Uani 1 1 d . . . C9 C 0.74804(17) 0.62248(16) 0.09850(7) 0.0693(7) Uani 1 1 d . . . C10 C 0.77123(16) 0.63593(16) 0.06534(7) 0.0673(7) Uani 1 1 d . . . H10 H 0.7407 0.6786 0.0530 0.081 Uiso 1 1 calc R . . C11 C 0.76689(18) 0.54175(19) 0.15370(7) 0.0762(7) Uani 1 1 d . . . H11A H 0.7053 0.5585 0.1573 0.091 Uiso 1 1 calc R . . H11B H 0.7724 0.4788 0.1586 0.091 Uiso 1 1 calc R . . C12 C 0.82539(17) 0.59355(17) 0.17759(6) 0.0675(6) Uani 1 1 d . . . C13 C 0.90700(18) 0.56064(17) 0.18793(6) 0.0690(7) Uani 1 1 d . . . C14 C 0.96131(18) 0.60998(19) 0.20858(6) 0.0715(7) Uani 1 1 d . . . H14 H 1.0155 0.5862 0.2153 0.086 Uiso 1 1 calc R . . C15 C 0.93717(17) 0.69473(18) 0.21969(6) 0.0672(6) Uani 1 1 d . . . C16 C 0.85439(18) 0.72720(18) 0.20990(7) 0.0735(7) Uani 1 1 d . . . C17 C 0.79974(18) 0.67691(19) 0.18940(7) 0.0745(7) Uani 1 1 d . . . H17 H 0.7444 0.6994 0.1833 0.089 Uiso 1 1 calc R . . C18 C 1.0000 0.7500 0.24059(9) 0.0743(10) Uani 1 2 d S . . H18A H 1.0344 0.7108 0.2548 0.089 Uiso 0.50 1 calc PR . . H18B H 0.9656 0.7892 0.2548 0.089 Uiso 0.50 1 calc PR . . C19 C 1.2075(2) 0.62041(18) 0.01637(8) 0.0854(8) Uani 1 1 d U . . H19A H 1.1826 0.5928 0.0358 0.128 Uiso 1 1 calc R . . H19B H 1.2712 0.6179 0.0175 0.128 Uiso 1 1 calc R . . H19C H 1.1874 0.5895 -0.0032 0.128 Uiso 1 1 calc R . . C20 C 1.0083(2) 0.4271(2) 0.07176(7) 0.0859(8) Uani 1 1 d . . . H20A H 1.0365 0.4652 0.0878 0.129 Uiso 1 1 calc R . . H20B H 1.0525 0.4021 0.0572 0.129 Uiso 1 1 calc R . . H20C H 0.9776 0.3800 0.0832 0.129 Uiso 1 1 calc R . . C21 C 0.6453(3) 0.7429(3) 0.09646(12) 0.150(2) Uani 1 1 d . . . H21A H 0.6917 0.7804 0.0879 0.225 Uiso 1 1 calc R . . H21B H 0.6075 0.7768 0.1110 0.225 Uiso 1 1 calc R . . H21C H 0.6108 0.7199 0.0782 0.225 Uiso 1 1 calc R . . C22 C 1.0159(3) 0.4462(2) 0.17957(9) 0.1128(12) Uani 1 1 d . . . H22A H 1.0565 0.4919 0.1727 0.169 Uiso 1 1 calc R . . H22B H 1.0243 0.3944 0.1659 0.169 Uiso 1 1 calc R . . H22C H 1.0268 0.4311 0.2025 0.169 Uiso 1 1 calc R . . C23 C 0.7484(3) 0.8465(3) 0.21323(11) 0.1323(16) Uani 1 1 d . . . H23A H 0.7477 0.8598 0.1898 0.198 Uiso 1 1 calc R . . H23B H 0.7383 0.9000 0.2257 0.198 Uiso 1 1 calc R . . H23C H 0.7026 0.8041 0.2182 0.198 Uiso 1 1 calc R . . C24 C 0.8540(9) 0.8614(9) 0.1403(3) 0.198(5) Uani 0.50 1 d P A 1 H24A H 0.8463 0.9245 0.1379 0.297 Uiso 0.50 1 calc PR A 1 H24B H 0.8752 0.8486 0.1624 0.297 Uiso 0.50 1 calc PR A 1 H24C H 0.7981 0.8320 0.1368 0.297 Uiso 0.50 1 calc PR A 1 C25 C 0.9157(4) 0.8313(3) 0.11696(11) 0.1217(14) Uani 0.50 1 d P A 1 O6 O 0.9127(10) 0.8649(9) 0.0939(3) 0.314(9) Uani 0.50 1 d P A 1 O7 O 0.9666(3) 0.7644(4) 0.11752(16) 0.209(2) Uani 0.50 1 d P . 1 C25' C 0.9157(4) 0.8313(3) 0.11696(11) 0.1217(14) Uani 0.50 1 d P B 2 H25A H 0.9425 0.8792 0.1292 0.183 Uiso 0.50 1 calc PR B 2 H25B H 0.8597 0.8161 0.1270 0.183 Uiso 0.50 1 calc PR B 2 H25C H 0.9061 0.8494 0.0943 0.183 Uiso 0.50 1 calc PR B 2 C26 C 0.9666(3) 0.7644(4) 0.11752(16) 0.209(2) Uani 0.50 1 d P . 2 H26A H 0.9428 0.7348 0.1371 0.251 Uiso 0.50 1 calc PR . 2 H26B H 0.9414 0.7314 0.0990 0.251 Uiso 0.50 1 calc PR . 2 O1 O 1.17987(12) 0.71003(11) 0.01483(4) 0.0740(5) Uani 1 1 d U . . O2 O 0.94753(15) 0.47638(14) 0.05297(4) 0.0912(6) Uani 1 1 d U . . O3 O 0.68324(14) 0.67182(14) 0.11436(6) 0.1001(7) Uani 1 1 d . . . O4 O 0.92840(15) 0.47677(13) 0.17608(5) 0.0949(6) Uani 1 1 d . . . O5 O 0.83239(14) 0.81031(14) 0.22199(6) 0.0990(7) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0677(15) 0.0525(13) 0.0575(12) -0.0026(10) 0.0035(10) -0.0022(11) C2 0.0768(17) 0.0463(12) 0.0596(13) -0.0066(10) -0.0004(11) -0.0032(11) C3 0.0745(16) 0.0484(13) 0.0519(12) -0.0049(9) -0.0027(10) -0.0054(11) C4 0.0793(17) 0.0533(14) 0.0670(14) -0.0087(11) -0.0081(12) -0.0099(12) C5 0.0585(14) 0.0448(12) 0.0740(14) -0.0069(10) -0.0045(11) -0.0108(10) C6 0.0633(15) 0.0539(14) 0.0738(15) -0.0125(11) -0.0025(11) -0.0011(11) C7 0.0659(16) 0.0548(14) 0.0758(15) -0.0014(11) -0.0020(12) -0.0022(11) C8 0.0554(14) 0.0532(13) 0.0814(16) 0.0008(11) 0.0060(11) -0.0127(11) C9 0.0559(14) 0.0539(14) 0.0981(19) -0.0008(12) 0.0167(12) -0.0054(11) C10 0.0593(15) 0.0497(13) 0.0930(18) 0.0058(11) -0.0001(12) -0.0082(11) C11 0.0666(16) 0.0675(16) 0.0945(19) 0.0079(13) 0.0176(13) -0.0108(13) C12 0.0617(15) 0.0698(16) 0.0709(14) 0.0100(12) 0.0143(11) 0.0028(12) C13 0.0737(17) 0.0624(15) 0.0710(15) 0.0109(12) 0.0145(12) 0.0117(13) C14 0.0679(16) 0.0777(18) 0.0689(15) 0.0109(13) 0.0059(12) 0.0200(13) C15 0.0652(15) 0.0749(16) 0.0616(14) 0.0068(11) 0.0084(11) 0.0138(12) C16 0.0670(17) 0.0716(17) 0.0818(17) -0.0032(13) 0.0030(13) 0.0183(13) C17 0.0597(15) 0.0779(18) 0.0859(18) 0.0020(14) 0.0056(13) 0.0125(13) C18 0.070(2) 0.087(3) 0.067(2) 0.000 0.000 0.018(2) C19 0.081(2) 0.0615(17) 0.114(2) 0.0029(15) 0.0001(16) 0.0073(14) C20 0.0769(19) 0.087(2) 0.0937(19) -0.0028(15) 0.0036(15) 0.0180(15) C21 0.151(4) 0.098(3) 0.202(5) 0.051(3) 0.082(3) 0.066(3) C22 0.120(3) 0.102(3) 0.116(3) -0.011(2) -0.010(2) 0.053(2) C23 0.110(3) 0.118(3) 0.169(4) -0.049(3) -0.048(3) 0.065(2) C24 0.231(13) 0.201(12) 0.163(10) 0.022(9) 0.037(9) 0.076(10) C25 0.149(4) 0.113(3) 0.103(3) 0.018(2) 0.018(3) -0.004(3) O6 0.412(19) 0.308(14) 0.224(10) 0.118(10) 0.128(11) 0.185(14) O7 0.130(4) 0.145(4) 0.353(7) 0.052(5) -0.009(4) 0.031(4) C25' 0.149(4) 0.113(3) 0.103(3) 0.018(2) 0.018(3) -0.004(3) C26 0.130(4) 0.145(4) 0.353(7) 0.052(5) -0.009(4) 0.031(4) O1 0.0725(12) 0.0553(10) 0.0942(12) -0.0061(8) 0.0040(9) -0.0005(8) O2 0.1048(15) 0.0944(14) 0.0744(11) -0.0076(10) 0.0028(10) 0.0406(12) O3 0.0870(14) 0.0849(14) 0.1283(17) 0.0187(12) 0.0425(12) 0.0223(11) O4 0.1009(16) 0.0701(13) 0.1136(15) -0.0027(11) -0.0041(12) 0.0257(11) O5 0.0832(14) 0.0899(15) 0.1239(17) -0.0265(12) -0.0202(12) 0.0355(12) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 O1 1.384(3) . ? C1 C2 1.386(3) . ? C1 C3 1.394(3) 6_664 ? C2 C3 1.388(3) . ? C2 H2 0.9300 . ? C3 C1 1.394(3) 6_664 ? C3 C4 1.515(3) . ? C4 C5 1.515(3) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C5 C10 1.384(3) . ? C5 C6 1.391(3) . ? C6 O2 1.379(3) . ? C6 C7 1.395(3) . ? C7 C8 1.387(3) . ? C7 H7 0.9300 . ? C8 C9 1.389(4) . ? C8 C11 1.517(3) . ? C9 O3 1.379(3) . ? C9 C10 1.388(3) . ? C10 H10 0.9300 . ? C11 C12 1.515(4) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 C13 1.386(4) . ? C12 C17 1.394(4) . ? C13 C14 1.379(4) . ? C13 O4 1.385(3) . ? C14 C15 1.397(3) . ? C14 H14 0.9300 . ? C15 C16 1.393(4) . ? C15 C18 1.511(3) . ? C16 O5 1.380(3) . ? C16 C17 1.386(4) . ? C17 H17 0.9300 . ? C18 C15 1.511(3) 6_664 ? C18 H18A 0.9700 . ? C18 H18B 0.9700 . ? C19 O1 1.411(3) . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 0.9600 . ? C20 O2 1.397(3) . ? C20 H20A 0.9600 . ? C20 H20B 0.9600 . ? C20 H20C 0.9600 . ? C21 O3 1.408(4) . ? C21 H21A 0.9600 . ? C21 H21B 0.9600 . ? C21 H21C 0.9600 . ? C22 O4 1.400(4) . ? C22 H22A 0.9600 . ? C22 H22B 0.9600 . ? C22 H22C 0.9600 . ? C23 O5 1.418(4) . ? C23 H23A 0.9600 . ? C23 H23B 0.9600 . ? C23 H23C 0.9600 . ? C24 C25 1.393(11) . ? C24 H24A 0.9600 . ? C24 H24B 0.9600 . ? C24 H24C 0.9600 . ? C25 O6 1.056(9) . ? C25 O7 1.264(6) . ? O7 O7 1.094(8) 6_664 ? 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 O1 C1 C2 123.5(2) . . ? O1 C1 C3 116.4(2) . 6_664 ? C2 C1 C3 120.1(2) . 6_664 ? C1 C2 C3 121.4(2) . . ? C1 C2 H2 119.3 . . ? C3 C2 H2 119.3 . . ? C2 C3 C1 118.4(2) . 6_664 ? C2 C3 C4 120.1(2) . . ? C1 C3 C4 121.4(2) 6_664 . ? C3 C4 C5 111.36(18) . . ? C3 C4 H4A 109.4 . . ? C5 C4 H4A 109.4 . . ? C3 C4 H4B 109.4 . . ? C5 C4 H4B 109.4 . . ? H4A C4 H4B 108.0 . . ? C10 C5 C6 117.5(2) . . ? C10 C5 C4 120.1(2) . . ? C6 C5 C4 122.3(2) . . ? O2 C6 C5 115.9(2) . . ? O2 C6 C7 123.5(2) . . ? C5 C6 C7 120.6(2) . . ? C8 C7 C6 121.5(2) . . ? C8 C7 H7 119.3 . . ? C6 C7 H7 119.3 . . ? C7 C8 C9 117.8(2) . . ? C7 C8 C11 120.5(2) . . ? C9 C8 C11 121.7(2) . . ? O3 C9 C10 122.7(2) . . ? O3 C9 C8 116.8(2) . . ? C10 C9 C8 120.6(2) . . ? C5 C10 C9 122.0(2) . . ? C5 C10 H10 119.0 . . ? C9 C10 H10 119.0 . . ? C12 C11 C8 113.1(2) . . ? C12 C11 H11A 109.0 . . ? C8 C11 H11A 109.0 . . ? C12 C11 H11B 109.0 . . ? C8 C11 H11B 109.0 . . ? H11A C11 H11B 107.8 . . ? C13 C12 C17 117.7(3) . . ? C13 C12 C11 121.3(2) . . ? C17 C12 C11 121.1(2) . . ? C14 C13 O4 123.9(2) . . ? C14 C13 C12 120.8(2) . . ? O4 C13 C12 115.3(3) . . ? C13 C14 C15 121.9(2) . . ? C13 C14 H14 119.1 . . ? C15 C14 H14 119.1 . . ? C16 C15 C14 117.5(3) . . ? C16 C15 C18 121.4(2) . . ? C14 C15 C18 121.0(2) . . ? O5 C16 C17 124.0(2) . . ? O5 C16 C15 115.6(2) . . ? C17 C16 C15 120.3(2) . . ? C16 C17 C12 121.8(2) . . ? C16 C17 H17 119.1 . . ? C12 C17 H17 119.1 . . ? C15 C18 C15 112.7(3) . 6_664 ? C15 C18 H18A 109.1 . . ? C15 C18 H18A 109.1 6_664 . ? C15 C18 H18B 109.1 . . ? C15 C18 H18B 109.1 6_664 . ? H18A C18 H18B 107.8 . . ? O1 C19 H19A 109.5 . . ? O1 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? O1 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? O2 C20 H20A 109.5 . . ? O2 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? O2 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? O3 C21 H21A 109.5 . . ? O3 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? O3 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? O4 C22 H22A 109.5 . . ? O4 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? O4 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? O5 C23 H23A 109.5 . . ? O5 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? O5 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? 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 . . ? O6 C25 O7 114.9(8) . . ? O6 C25 C24 114.0(9) . . ? O7 C25 C24 130.5(7) . . ? O7 O7 C25 150.5(9) 6_664 . ? C1 O1 C19 118.2(2) . . ? C6 O2 C20 119.5(2) . . ? C9 O3 C21 117.3(2) . . ? C13 O4 C22 118.9(3) . . ? C16 O5 C23 118.2(2) . . ? 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 O1 C1 C2 C3 178.6(2) . . . . ? C3 C1 C2 C3 -2.5(3) 6_664 . . . ? C1 C2 C3 C1 0.8(3) . . . 6_664 ? C1 C2 C3 C4 -177.4(2) . . . . ? C2 C3 C4 C5 92.9(3) . . . . ? C1 C3 C4 C5 -85.2(3) 6_664 . . . ? C3 C4 C5 C10 86.1(3) . . . . ? C3 C4 C5 C6 -90.7(3) . . . . ? C10 C5 C6 O2 179.9(2) . . . . ? C4 C5 C6 O2 -3.3(3) . . . . ? C10 C5 C6 C7 0.7(3) . . . . ? C4 C5 C6 C7 177.5(2) . . . . ? O2 C6 C7 C8 178.6(2) . . . . ? C5 C6 C7 C8 -2.2(4) . . . . ? C6 C7 C8 C9 1.6(3) . . . . ? C6 C7 C8 C11 -177.4(2) . . . . ? C7 C8 C9 O3 -179.5(2) . . . . ? C11 C8 C9 O3 -0.5(4) . . . . ? C7 C8 C9 C10 0.5(4) . . . . ? C11 C8 C9 C10 179.4(2) . . . . ? C6 C5 C10 C9 1.5(3) . . . . ? C4 C5 C10 C9 -175.4(2) . . . . ? O3 C9 C10 C5 177.9(2) . . . . ? C8 C9 C10 C5 -2.1(4) . . . . ? C7 C8 C11 C12 86.0(3) . . . . ? C9 C8 C11 C12 -92.9(3) . . . . ? C8 C11 C12 C13 -85.2(3) . . . . ? C8 C11 C12 C17 93.5(3) . . . . ? C17 C12 C13 C14 -1.4(4) . . . . ? C11 C12 C13 C14 177.3(2) . . . . ? C17 C12 C13 O4 178.6(2) . . . . ? C11 C12 C13 O4 -2.7(3) . . . . ? O4 C13 C14 C15 179.5(2) . . . . ? C12 C13 C14 C15 -0.5(4) . . . . ? C13 C14 C15 C16 1.8(4) . . . . ? C13 C14 C15 C18 -176.3(2) . . . . ? C14 C15 C16 O5 178.7(2) . . . . ? C18 C15 C16 O5 -3.3(4) . . . . ? C14 C15 C16 C17 -1.2(4) . . . . ? C18 C15 C16 C17 176.9(3) . . . . ? O5 C16 C17 C12 179.4(3) . . . . ? C15 C16 C17 C12 -0.8(4) . . . . ? C13 C12 C17 C16 2.0(4) . . . . ? C11 C12 C17 C16 -176.7(2) . . . . ? C16 C15 C18 C15 -90.6(2) . . . 6_664 ? C14 C15 C18 C15 87.3(2) . . . 6_664 ? O6 C25 O7 O7 71.8(15) . . . 6_664 ? C24 C25 O7 O7 -117.7(10) . . . 6_664 ? C2 C1 O1 C19 -3.0(3) . . . . ? C3 C1 O1 C19 178.0(2) 6_664 . . . ? C5 C6 O2 C20 164.0(2) . . . . ? C7 C6 O2 C20 -16.8(4) . . . . ? C10 C9 O3 C21 -5.2(4) . . . . ? C8 C9 O3 C21 174.7(3) . . . . ? C14 C13 O4 C22 -12.8(4) . . . . ? C12 C13 O4 C22 167.2(3) . . . . ? C17 C16 O5 C23 0.6(5) . . . . ? C15 C16 O5 C23 -179.2(3) . . . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 27.47 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.256 _refine_diff_density_min -0.340 _refine_diff_density_rms 0.035 _database_code_depnum_ccdc_archive 'CCDC 968775' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_tll0432 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C45 H50 O10, C3 H6 O' _chemical_formula_sum 'C48 H56 O11' _chemical_formula_weight 808.93 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 tetragonal _symmetry_space_group_name_H-M 'I 4(1)/a' _symmetry_space_group_name_HALL '-I 4ad' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-y+3/4, x+1/4, z+1/4' 'y+3/4, -x+3/4, z+3/4' 'x+1/2, y+1/2, z+1/2' '-x+1, -y+1/2, z+1' '-y+5/4, x+3/4, z+3/4' 'y+5/4, -x+5/4, z+5/4' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'y-3/4, -x-1/4, -z-1/4' '-y-3/4, x-3/4, -z-3/4' '-x+1/2, -y+1/2, -z+1/2' 'x, y+1/2, -z' 'y-1/4, -x+1/4, -z+1/4' '-y-1/4, x-1/4, -z-1/4' _cell_length_a 14.9380(5) _cell_length_b 14.9380(5) _cell_length_c 39.779(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 8876.5(8) _cell_formula_units_Z 8 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.32 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.211 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 3456 _exptl_absorpt_coefficient_mu 0.085 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9708 _exptl_absorpt_correction_T_max 0.9749 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 32684 _diffrn_reflns_av_R_equivalents 0.0547 _diffrn_reflns_av_sigmaI/netI 0.0433 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -52 _diffrn_reflns_limit_l_max 53 _diffrn_reflns_theta_min 1.46 _diffrn_reflns_theta_max 28.32 _reflns_number_total 5521 _reflns_number_gt 2316 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0988P)^2^+1.1719P] 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 5521 _refine_ls_number_parameters 289 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.1518 _refine_ls_R_factor_gt 0.0622 _refine_ls_wR_factor_ref 0.2206 _refine_ls_wR_factor_gt 0.1717 _refine_ls_goodness_of_fit_ref 1.048 _refine_ls_restrained_S_all 1.053 _refine_ls_shift/su_max 0.016 _refine_ls_shift/su_mean 0.003 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.5000 0.2500 0.24203(10) 0.0842(12) Uani 1 2 d S . . H1A H 0.5350 0.2890 0.2564 0.101 Uiso 0.50 1 calc PR . . H1B H 0.4650 0.2110 0.2564 0.101 Uiso 0.50 1 calc PR . . C2 C 0.56259(18) 0.19386(19) 0.22116(7) 0.0752(7) Uani 1 1 d . . . C3 C 0.5386(2) 0.1090(2) 0.21012(7) 0.0789(8) Uani 1 1 d . . . H3 H 0.4842 0.0850 0.2171 0.095 Uiso 1 1 calc R . . C4 C 0.5923(2) 0.05946(18) 0.18936(7) 0.0769(8) Uani 1 1 d . . . C5 C 0.67459(18) 0.09173(18) 0.17890(7) 0.0744(7) Uani 1 1 d . . . C6 C 0.70065(19) 0.1752(2) 0.19089(8) 0.0842(9) Uani 1 1 d . . . H6 H 0.7567 0.1975 0.1851 0.101 Uiso 1 1 calc R . . C7 C 0.6451(2) 0.2257(2) 0.21121(8) 0.0840(8) Uani 1 1 d . . . C8 C 0.73294(18) 0.03923(19) 0.15490(7) 0.0820(8) Uani 1 1 d . . . H8A H 0.7950 0.0555 0.1586 0.098 Uiso 1 1 calc R . . H8B H 0.7268 -0.0241 0.1598 0.098 Uiso 1 1 calc R . . C9 C 0.70969(16) 0.05547(16) 0.11847(7) 0.0677(7) Uani 1 1 d . . . C10 C 0.64491(17) 0.00430(16) 0.10257(7) 0.0695(7) Uani 1 1 d . . . H10 H 0.6176 -0.0422 0.1143 0.083 Uiso 1 1 calc R . . C11 C 0.61991(17) 0.02094(16) 0.06951(7) 0.0669(7) Uani 1 1 d . . . C12 C 0.66216(16) 0.08698(15) 0.05110(6) 0.0627(6) Uani 1 1 d . . . C13 C 0.72726(17) 0.13660(17) 0.06675(7) 0.0733(8) Uani 1 1 d . . . H13 H 0.7567 0.1811 0.0547 0.088 Uiso 1 1 calc R . . C14 C 0.75014(17) 0.12217(16) 0.09994(8) 0.0760(8) Uani 1 1 d . . . C15 C 0.63470(18) 0.10917(16) 0.01531(6) 0.0703(7) Uani 1 1 d . . . H15A H 0.6870 0.1277 0.0027 0.084 Uiso 1 1 calc R . . H15B H 0.6104 0.0560 0.0047 0.084 Uiso 1 1 calc R . . C16 C 0.56566(17) 0.18285(15) 0.01446(6) 0.0611(6) Uani 1 1 d . . . C17 C 0.58975(17) 0.27221(15) 0.01464(6) 0.0610(6) Uani 1 1 d . . . C18 C 0.52442(18) 0.33822(15) 0.01430(6) 0.0636(6) Uani 1 1 d . . . H18 H 0.5417 0.3980 0.0139 0.076 Uiso 1 1 calc R . . C19 C 0.4795(3) -0.0517(3) 0.17852(10) 0.1258(14) Uani 1 1 d . . . H19A H 0.4610 -0.0585 0.2015 0.189 Uiso 1 1 calc R . . H19B H 0.4728 -0.1077 0.1670 0.189 Uiso 1 1 calc R . . H19C H 0.4431 -0.0071 0.1678 0.189 Uiso 1 1 calc R . . C20 C 0.7482(3) 0.3494(3) 0.21138(11) 0.1370(16) Uani 1 1 d . . . H20A H 0.7977 0.3115 0.2172 0.206 Uiso 1 1 calc R . . H20B H 0.7558 0.4069 0.2217 0.206 Uiso 1 1 calc R . . H20C H 0.7457 0.3563 0.1874 0.206 Uiso 1 1 calc R . . C21 C 0.4908(2) -0.0727(2) 0.07172(8) 0.0983(10) Uani 1 1 d . . . H21A H 0.5183 -0.1228 0.0828 0.147 Uiso 1 1 d R . . H21B H 0.4443 -0.0938 0.0571 0.147 Uiso 1 1 d R . . H21C H 0.4657 -0.0331 0.0882 0.147 Uiso 1 1 d R . . C22 C 0.8453(4) 0.2494(3) 0.10095(14) 0.193(3) Uani 1 1 d . . . H22A H 0.8669 0.2347 0.0789 0.290 Uiso 1 1 calc R . . H22B H 0.8932 0.2745 0.1140 0.290 Uiso 1 1 calc R . . H22C H 0.7976 0.2922 0.0991 0.290 Uiso 1 1 calc R . . C23 C 0.7084(2) 0.38000(18) 0.01769(8) 0.0910(9) Uani 1 1 d . . . H23A H 0.6906 0.4123 -0.0021 0.136 Uiso 1 1 calc R . . H23B H 0.7724 0.3821 0.0199 0.136 Uiso 1 1 calc R . . H23C H 0.6813 0.4067 0.0371 0.136 Uiso 1 1 calc R . . C24 C 0.5531(7) 0.3117(6) 0.1140(2) 0.132(3) Uani 0.50 1 d PD A -1 C25 C 0.5963(11) 0.3670(11) 0.0900(3) 0.288(10) Uani 0.50 1 d PD A -1 H25A H 0.5792 0.4277 0.0947 0.432 Uiso 0.50 1 d PR A -1 H25B H 0.5753 0.3505 0.0681 0.432 Uiso 0.50 1 d PR A -1 H25C H 0.6603 0.3619 0.0908 0.432 Uiso 0.50 1 d PR A -1 C26 C 0.5048(13) 0.2296(6) 0.1083(3) 0.182(6) Uani 0.50 1 d PD A -1 H26A H 0.5118 0.1933 0.1281 0.273 Uiso 0.50 1 d PR A -1 H26B H 0.5277 0.1980 0.0891 0.273 Uiso 0.50 1 d PR A -1 H26C H 0.4425 0.2424 0.1049 0.273 Uiso 0.50 1 d PR A -1 O6 O 0.6079(12) 0.3380(14) 0.1351(3) 0.435(12) Uani 0.50 1 d PD A -1 O1 O 0.56991(15) -0.02503(14) 0.17751(6) 0.1030(7) Uani 1 1 d . . . O2 O 0.66759(14) 0.31010(15) 0.22291(6) 0.1151(8) Uani 1 1 d . . . O3 O 0.55449(15) -0.02745(14) 0.05299(5) 0.0985(7) Uani 1 1 d . . . O4 O 0.81379(15) 0.17251(14) 0.11657(6) 0.1134(8) Uani 1 1 d . . . O5 O 0.68043(12) 0.29016(11) 0.01494(5) 0.0781(5) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.079(3) 0.092(3) 0.082(3) 0.000 0.000 -0.023(2) C2 0.0719(17) 0.0817(19) 0.0718(18) 0.0088(14) -0.0075(14) -0.0170(15) C3 0.0760(18) 0.086(2) 0.0752(18) 0.0111(15) -0.0054(14) -0.0250(16) C4 0.084(2) 0.0698(17) 0.0773(19) 0.0091(14) -0.0134(15) -0.0166(15) C5 0.0685(17) 0.0739(18) 0.0807(18) 0.0108(14) -0.0198(14) -0.0050(15) C6 0.0627(16) 0.0811(19) 0.109(2) -0.0009(17) -0.0078(16) -0.0151(15) C7 0.0756(19) 0.0815(19) 0.095(2) -0.0050(16) -0.0043(16) -0.0209(16) C8 0.0728(17) 0.0700(17) 0.103(2) 0.0104(16) -0.0227(16) 0.0074(14) C9 0.0617(15) 0.0538(14) 0.0875(19) -0.0002(13) -0.0122(13) 0.0111(12) C10 0.0710(17) 0.0549(14) 0.0826(19) -0.0018(13) 0.0043(14) 0.0008(13) C11 0.0687(16) 0.0575(14) 0.0743(18) -0.0103(13) 0.0032(13) -0.0003(13) C12 0.0615(15) 0.0459(13) 0.0805(17) -0.0054(12) 0.0049(13) 0.0105(11) C13 0.0614(15) 0.0531(14) 0.105(2) 0.0116(14) -0.0070(15) 0.0073(12) C14 0.0612(16) 0.0536(15) 0.113(2) 0.0067(15) -0.0234(15) 0.0039(12) C15 0.0810(17) 0.0513(14) 0.0786(18) -0.0069(12) 0.0099(14) 0.0099(12) C16 0.0771(17) 0.0508(14) 0.0553(14) -0.0037(10) 0.0023(12) 0.0051(12) C17 0.0697(16) 0.0523(14) 0.0611(15) 0.0007(11) 0.0025(12) 0.0019(13) C18 0.0829(18) 0.0458(13) 0.0621(15) 0.0082(11) -0.0027(13) 0.0018(13) C19 0.124(3) 0.129(3) 0.124(3) -0.028(2) 0.015(2) -0.069(3) C20 0.114(3) 0.114(3) 0.183(4) -0.041(3) 0.047(3) -0.059(2) C21 0.080(2) 0.113(2) 0.102(2) 0.0003(19) -0.0077(17) -0.0254(18) C22 0.213(5) 0.108(3) 0.260(6) 0.076(4) -0.133(5) -0.088(3) C23 0.0823(19) 0.0658(18) 0.125(3) -0.0051(16) -0.0011(17) -0.0087(15) C24 0.160(9) 0.136(8) 0.100(6) -0.026(6) -0.032(6) 0.018(7) C25 0.33(2) 0.34(2) 0.194(13) 0.037(14) -0.104(13) -0.184(18) C26 0.233(13) 0.081(11) 0.233(11) -0.006(7) 0.093(13) -0.026(12) O6 0.55(3) 0.42(2) 0.340(19) 0.002(16) 0.022(18) -0.21(2) O1 0.1117(17) 0.0791(13) 0.1181(17) -0.0053(12) 0.0036(13) -0.0330(12) O2 0.0938(15) 0.0947(15) 0.157(2) -0.0370(14) 0.0270(14) -0.0389(13) O3 0.1130(16) 0.1070(16) 0.0755(13) -0.0121(11) 0.0010(11) -0.0508(13) O4 0.1038(16) 0.0821(14) 0.154(2) 0.0285(13) -0.0598(15) -0.0297(12) O5 0.0755(12) 0.0575(10) 0.1012(14) 0.0053(9) 0.0035(10) 0.0014(9) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.506(4) . ? C1 C2 1.506(4) 6_554 ? C1 H1A 0.9700 . ? C1 H1B 0.9700 . ? C2 C7 1.379(4) . ? C2 C3 1.388(4) . ? C3 C4 1.369(4) . ? C3 H3 0.9300 . ? C4 C5 1.384(4) . ? C4 O1 1.388(3) . ? C5 C6 1.391(4) . ? C5 C8 1.512(4) . ? C6 C7 1.383(4) . ? C6 H6 0.9300 . ? C7 O2 1.385(3) . ? C8 C9 1.510(4) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 C14 1.379(4) . ? C9 C10 1.386(3) . ? C10 C11 1.390(3) . ? C10 H10 0.9300 . ? C11 C12 1.381(3) . ? C11 O3 1.382(3) . ? C12 C13 1.372(3) . ? C12 C15 1.518(3) . ? C13 C14 1.381(4) . ? C13 H13 0.9300 . ? C14 O4 1.381(3) . ? C15 C16 1.509(3) . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C16 C18 1.382(3) 6_554 ? C16 C17 1.382(3) . ? C17 O5 1.381(3) . ? C17 C18 1.387(3) . ? C18 C16 1.382(3) 6_554 ? C18 H18 0.9300 . ? C19 O1 1.408(4) . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 0.9600 . ? C20 O2 1.416(4) . ? C20 H20A 0.9600 . ? C20 H20B 0.9600 . ? C20 H20C 0.9600 . ? C21 O3 1.385(3) . ? C21 H21A 0.9600 . ? C21 H21B 0.9600 . ? C21 H21C 0.9600 . ? C22 O4 1.389(4) . ? C22 H22A 0.9600 . ? C22 H22B 0.9600 . ? C22 H22C 0.9600 . ? C23 O5 1.410(3) . ? C23 H23A 0.9600 . ? C23 H23B 0.9600 . ? C23 H23C 0.9600 . ? C24 O6 1.237(5) . ? C24 C25 1.417(5) . ? C24 C26 1.441(5) . ? C25 O6 1.854(17) . ? C25 H25A 0.9600 . ? C25 H25B 0.9600 . ? C25 H25C 0.9600 . ? C26 H26A 0.9600 . ? C26 H26B 0.9600 . ? C26 H26C 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 C1 C2 113.1(3) . 6_554 ? C2 C1 H1A 109.0 . . ? C2 C1 H1A 109.0 6_554 . ? C2 C1 H1B 109.0 . . ? C2 C1 H1B 109.0 6_554 . ? H1A C1 H1B 107.8 . . ? C7 C2 C3 117.1(3) . . ? C7 C2 C1 121.4(2) . . ? C3 C2 C1 121.5(2) . . ? C4 C3 C2 122.2(3) . . ? C4 C3 H3 118.9 . . ? C2 C3 H3 118.9 . . ? C3 C4 C5 120.9(3) . . ? C3 C4 O1 123.7(3) . . ? C5 C4 O1 115.4(3) . . ? C4 C5 C6 117.2(3) . . ? C4 C5 C8 121.4(3) . . ? C6 C5 C8 121.3(3) . . ? C7 C6 C5 121.4(3) . . ? C7 C6 H6 119.3 . . ? C5 C6 H6 119.3 . . ? C2 C7 C6 121.1(3) . . ? C2 C7 O2 115.8(3) . . ? C6 C7 O2 123.2(3) . . ? C9 C8 C5 113.0(2) . . ? C9 C8 H8A 109.0 . . ? C5 C8 H8A 109.0 . . ? C9 C8 H8B 109.0 . . ? C5 C8 H8B 109.0 . . ? H8A C8 H8B 107.8 . . ? C14 C9 C10 117.4(2) . . ? C14 C9 C8 121.9(2) . . ? C10 C9 C8 120.7(2) . . ? C9 C10 C11 121.4(2) . . ? C9 C10 H10 119.3 . . ? C11 C10 H10 119.3 . . ? C12 C11 O3 116.4(2) . . ? C12 C11 C10 120.5(2) . . ? O3 C11 C10 123.1(2) . . ? C13 C12 C11 118.0(2) . . ? C13 C12 C15 119.9(2) . . ? C11 C12 C15 122.0(2) . . ? C12 C13 C14 121.7(2) . . ? C12 C13 H13 119.2 . . ? C14 C13 H13 119.2 . . ? C9 C14 C13 121.0(2) . . ? C9 C14 O4 116.0(3) . . ? C13 C14 O4 122.9(3) . . ? C16 C15 C12 111.40(19) . . ? C16 C15 H15A 109.3 . . ? C12 C15 H15A 109.3 . . ? C16 C15 H15B 109.3 . . ? C12 C15 H15B 109.3 . . ? H15A C15 H15B 108.0 . . ? C18 C16 C17 118.2(2) 6_554 . ? C18 C16 C15 120.0(2) 6_554 . ? C17 C16 C15 121.8(2) . . ? O5 C17 C16 116.3(2) . . ? O5 C17 C18 123.5(2) . . ? C16 C17 C18 120.2(2) . . ? C16 C18 C17 121.5(2) 6_554 . ? C16 C18 H18 119.2 6_554 . ? C17 C18 H18 119.2 . . ? O1 C19 H19A 109.5 . . ? O1 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? O1 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? O2 C20 H20A 109.5 . . ? O2 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? O2 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? O3 C21 H21A 109.5 . . ? O3 C21 H21B 109.3 . . ? H21A C21 H21B 109.5 . . ? O3 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? O4 C22 H22A 109.5 . . ? O4 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? O4 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? O5 C23 H23A 109.5 . . ? O5 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? O5 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? O6 C24 C25 88.3(10) . . ? O6 C24 C26 135.1(14) . . ? C25 C24 C26 128.2(10) . . ? C24 C25 O6 41.8(5) . . ? C24 C25 H25A 107.3 . . ? O6 C25 H25A 93.2 . . ? C24 C25 H25B 108.3 . . ? O6 C25 H25B 148.3 . . ? H25A C25 H25B 109.5 . . ? C24 C25 H25C 112.7 . . ? O6 C25 H25C 81.8 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? C24 C26 H26A 107.3 . . ? C24 C26 H26B 111.3 . . ? H26A C26 H26B 109.5 . . ? C24 C26 H26C 109.7 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? C24 O6 C25 49.8(6) . . ? C4 O1 C19 118.6(3) . . ? C7 O2 C20 118.4(3) . . ? C11 O3 C21 119.0(2) . . ? C14 O4 C22 118.0(3) . . ? C17 O5 C23 118.4(2) . . ? 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 C2 C1 C2 C7 90.0(3) 6_554 . . . ? C2 C1 C2 C3 -87.7(3) 6_554 . . . ? C7 C2 C3 C4 -2.1(4) . . . . ? C1 C2 C3 C4 175.7(3) . . . . ? C2 C3 C4 C5 1.2(4) . . . . ? C2 C3 C4 O1 -179.2(2) . . . . ? C3 C4 C5 C6 1.3(4) . . . . ? O1 C4 C5 C6 -178.4(2) . . . . ? C3 C4 C5 C8 -177.6(2) . . . . ? O1 C4 C5 C8 2.7(4) . . . . ? C4 C5 C6 C7 -2.8(4) . . . . ? C8 C5 C6 C7 176.0(3) . . . . ? C3 C2 C7 C6 0.5(4) . . . . ? C1 C2 C7 C6 -177.3(3) . . . . ? C3 C2 C7 O2 -179.3(3) . . . . ? C1 C2 C7 O2 2.8(4) . . . . ? C5 C6 C7 C2 2.0(5) . . . . ? C5 C6 C7 O2 -178.2(3) . . . . ? C4 C5 C8 C9 85.4(3) . . . . ? C6 C5 C8 C9 -93.4(3) . . . . ? C5 C8 C9 C14 90.7(3) . . . . ? C5 C8 C9 C10 -88.0(3) . . . . ? C14 C9 C10 C11 -1.6(4) . . . . ? C8 C9 C10 C11 177.1(2) . . . . ? C9 C10 C11 C12 2.8(4) . . . . ? C9 C10 C11 O3 -178.8(2) . . . . ? O3 C11 C12 C13 179.8(2) . . . . ? C10 C11 C12 C13 -1.7(4) . . . . ? O3 C11 C12 C15 3.5(3) . . . . ? C10 C11 C12 C15 -178.0(2) . . . . ? C11 C12 C13 C14 -0.5(4) . . . . ? C15 C12 C13 C14 175.9(2) . . . . ? C10 C9 C14 C13 -0.5(4) . . . . ? C8 C9 C14 C13 -179.3(2) . . . . ? C10 C9 C14 O4 179.4(2) . . . . ? C8 C9 C14 O4 0.7(4) . . . . ? C12 C13 C14 C9 1.6(4) . . . . ? C12 C13 C14 O4 -178.3(2) . . . . ? C13 C12 C15 C16 -84.2(3) . . . . ? C11 C12 C15 C16 92.0(3) . . . . ? C12 C15 C16 C18 -92.5(3) . . . 6_554 ? C12 C15 C16 C17 85.9(3) . . . . ? C18 C16 C17 O5 179.7(2) 6_554 . . . ? C15 C16 C17 O5 1.3(3) . . . . ? C18 C16 C17 C18 -0.7(3) 6_554 . . . ? C15 C16 C17 C18 -179.1(2) . . . . ? O5 C17 C18 C16 -179.1(2) . . . 6_554 ? C16 C17 C18 C16 1.3(3) . . . 6_554 ? C26 C24 C25 O6 -151(2) . . . . ? C26 C24 O6 C25 148(2) . . . . ? C3 C4 O1 C19 18.7(4) . . . . ? C5 C4 O1 C19 -161.7(3) . . . . ? C2 C7 O2 C20 -175.0(3) . . . . ? C6 C7 O2 C20 5.1(5) . . . . ? C12 C11 O3 C21 -159.2(2) . . . . ? C10 C11 O3 C21 22.3(4) . . . . ? C9 C14 O4 C22 -169.4(4) . . . . ? C13 C14 O4 C22 10.6(5) . . . . ? C16 C17 O5 C23 -175.3(2) . . . . ? C18 C17 O5 C23 5.2(4) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 28.32 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.239 _refine_diff_density_min -0.204 _refine_diff_density_rms 0.035 _database_code_depnum_ccdc_archive 'CCDC 968776'