data_antr _publ_contact_author_name 'Ba\/lczewski Piotr' _publ_contact_author_address ;Center of Molecular and Macromolecular Studies, Polish Academy of Sciences, Department of Heteroorganic Chemistry, ul. Sienkiewicza 112, Poland 90-363 Lodz Poland ; _publ_contact_author_email pbalczew@bilbo.cbmm.lodz.pl _publ_contact_author_phone '+48 42 6803202............' _publ_contact_author_fax '+48 42 6847126............' loop_ _publ_author_name _publ_author_address 'Ba\/lczewski, Piotr' ;Center of Molecular and Macromolecular Studies, Polish Academy of Sciences, Department of Heteroorganic Chemistry, ul. Sienkiewicza 112, Poland 90-363 Lodz Poland ; 'Koprowski, Maciej' ;Center of Molecular and Macromolecular Studies, Polish Academy of Sciences, Department of Heteroorganic Chemistry, ul. Sienkiewicza 112, Poland 90-363 Lodz Poland ; 'Bodzioch, Agnieszka' ;Center of Molecular and Macromolecular Studies, Polish Academy of Sciences, Department of Heteroorganic Chemistry, ul. Sienkiewicza 112, Poland 90-363 Lodz Poland ; 'Marciniak, Bernard' ;Institute of Chemistry and Environmental Protection Jan Dlugosz University ul. Armii Krajowej 13/15 42-200 Czestochowa Poland ; 'R\/o\/zycka-Soko\/lowska, Ewa' ;Institute of Chemistry and Environmental Protection Jan Dlugosz University ul. Armii Krajowej 13/15 42-200 Czestochowa Poland ; #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _audit_creation_method SHELXL-97 _chemical_name_systematic ; 10-benzyloxy-1,2,3-trimethoxy-6,7-(methylene-1,3-dioxy) anthracene ; _chemical_formula_sum 'C25 H22 O6' _chemical_formula_moiety 'C25 H22 O6' _chemical_formula_weight 418.43 #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.985(2) _cell_length_b 11.404(2) _cell_length_c 12.996(3) _cell_angle_alpha 113.74(3) _cell_angle_beta 92.24(3) _cell_angle_gamma 104.11(3) _cell_volume 1038.0(5) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 30 _cell_measurement_theta_min 7 _cell_measurement_theta_max 25 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description prismatic _exptl_crystal_colour 'clear pale yellow' _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.28 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.339 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 440 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.787 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 1.54180 _diffrn_radiation_type CuK\a _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'Kuma KM-4 diffractometer' _diffrn_measurement_method 'w-2theta scan' _diffrn_standards_number 3 _diffrn_standards_interval_count 100 _diffrn_standards_decay_% 1.04 _diffrn_reflns_av_R_equivalents 0.0882 _diffrn_reflns_av_sigmaI/netI 0.0866 _diffrn_reflns_number 7121 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 5.78 _diffrn_reflns_theta_max 67.90 _diffrn_reflns_theta_full 67.90 _diffrn_measured_fraction_theta_full 0.975 _diffrn_measured_fraction_theta_max 0.975 _reflns_number_total 3694 _reflns_number_gt 3161 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Kuma KM4B8 Software (Galdecki et al., 1996)' _computing_cell_refinement 'Kuma KM4B8 Software (Galdecki et al., 1996)' _computing_data_reduction 'Kuma KM4B8 Software (Galdecki et al., 1996)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-3 (Farrugia,1997), PLATON(Spek,2000)' _computing_publication_material SHELXL97 #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^)+(0.0711P)^2^+0.1844P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0032(9) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 3694 _refine_ls_number_parameters 287 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0609 _refine_ls_R_factor_gt 0.0549 _refine_ls_wR_factor_ref 0.1548 _refine_ls_wR_factor_gt 0.1484 _refine_ls_goodness_of_fit_ref 1.056 _refine_ls_restrained_S_all 1.056 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.344 _refine_diff_density_min -0.139 _refine_diff_density_rms 0.037 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0181 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' 0.0492 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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_symetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.8241(2) 0.70038(13) 1.00087(12) 0.0879(5) Uani 1 1 d . . . O2 O 0.8143(2) 0.53292(15) 1.05831(12) 0.0903(5) Uani 1 1 d . . . O3 O 0.46446(15) 0.08622(11) 0.73180(10) 0.0601(3) Uani 1 1 d . . . O4 O 0.10488(18) -0.13237(13) 0.33579(11) 0.0752(4) Uani 1 1 d . . . O5 O 0.10550(16) 0.06291(15) 0.27425(11) 0.0754(4) Uani 1 1 d . . . O6 O 0.29617(16) 0.32549(13) 0.41338(11) 0.0707(4) Uani 1 1 d . . . C1 C 0.8802(3) 0.6692(2) 1.08978(19) 0.0866(7) Uani 1 1 d . . . H1A H 1.0068 0.6948 1.1044 0.098(4) Uiso 1 1 calc R . . H1B H 0.8390 0.7187 1.1590 0.098(4) Uiso 1 1 calc R . . C2 C 0.7287(3) 0.57983(18) 0.91477(16) 0.0688(5) Uani 1 1 d . . . C3 C 0.6510(3) 0.55791(18) 0.81271(17) 0.0671(5) Uani 1 1 d . . . H3 H 0.6571 0.6275 0.7915 0.104(3) Uiso 1 1 calc R . . C4 C 0.5576(2) 0.42203(17) 0.73733(15) 0.0596(4) Uani 1 1 d . . . C5 C 0.4735(2) 0.38940(17) 0.62951(16) 0.0610(4) Uani 1 1 d . . . H5 H 0.4798 0.4567 0.6054 0.104(3) Uiso 1 1 calc R . . C6 C 0.3804(2) 0.25908(17) 0.55690(15) 0.0573(4) Uani 1 1 d . . . C7 C 0.2881(2) 0.22465(18) 0.44717(15) 0.0593(4) Uani 1 1 d . . . C8 C 0.2003(2) 0.09533(19) 0.37741(15) 0.0618(4) Uani 1 1 d . . . C9 C 0.1976(2) -0.00765(18) 0.41345(15) 0.0615(5) Uani 1 1 d . . . C10 C 0.2819(2) 0.02061(17) 0.51715(15) 0.0601(4) Uani 1 1 d . . . H10 H 0.2789 -0.0477 0.5395 0.104(3) Uiso 1 1 calc R . . C11 C 0.3746(2) 0.15461(17) 0.59151(14) 0.0555(4) Uani 1 1 d . . . C12 C 0.4617(2) 0.18742(16) 0.69967(15) 0.0562(4) Uani 1 1 d . . . C13 C 0.5517(2) 0.31853(17) 0.77417(14) 0.0565(4) Uani 1 1 d . . . C14 C 0.6388(2) 0.34990(19) 0.88470(16) 0.0656(5) Uani 1 1 d . . . H14 H 0.6369 0.2838 0.9097 0.104(3) Uiso 1 1 calc R . . C15 C 0.7226(3) 0.47807(19) 0.95015(16) 0.0683(5) Uani 1 1 d . . . C16 C 0.3164(3) 0.05064(18) 0.78372(17) 0.0679(5) Uani 1 1 d . . . H16A H 0.2105 0.0463 0.7415 0.098(4) Uiso 1 1 calc R . . H16B H 0.3297 0.1179 0.8610 0.098(4) Uiso 1 1 calc R . . C17 C 0.3032(2) -0.08291(19) 0.78446(17) 0.0665(5) Uani 1 1 d . . . C18 C 0.2397(4) -0.1120(3) 0.8685(3) 0.1059(8) Uani 1 1 d . . . H18 H 0.2122 -0.0460 0.9302 0.104(3) Uiso 1 1 calc R . . C19 C 0.2144(5) -0.2389(4) 0.8649(4) 0.1331(12) Uani 1 1 d . . . H19 H 0.1665 -0.2582 0.9223 0.104(3) Uiso 1 1 calc R . . C20 C 0.2607(4) -0.3356(3) 0.7760(4) 0.1206(11) Uani 1 1 d . . . H20 H 0.2505 -0.4191 0.7747 0.104(3) Uiso 1 1 calc R . . C21 C 0.3206(3) -0.3075(2) 0.6912(3) 0.0978(8) Uani 1 1 d . . . H21 H 0.3489 -0.3730 0.6296 0.104(3) Uiso 1 1 calc R . . C22 C 0.3404(3) -0.18409(19) 0.6944(2) 0.0752(5) Uani 1 1 d . . . H22 H 0.3804 -0.1676 0.6340 0.104(3) Uiso 1 1 calc R . . C23 C 0.0869(3) -0.2368(2) 0.37074(19) 0.0836(6) Uani 1 1 d . . . H23A H 0.2001 -0.2465 0.3862 0.126(3) Uiso 1 1 calc R . . H23B H 0.0150 -0.3188 0.3114 0.126(3) Uiso 1 1 calc R . . H23C H 0.0333 -0.2161 0.4383 0.126(3) Uiso 1 1 calc R . . C24 C 0.1952(3) 0.0327(3) 0.18076(18) 0.0956(7) Uani 1 1 d . . . H24A H 0.2860 0.1107 0.1905 0.126(3) Uiso 1 1 calc R . . H24B H 0.1152 0.0040 0.1125 0.126(3) Uiso 1 1 calc R . . H24C H 0.2458 -0.0375 0.1751 0.126(3) Uiso 1 1 calc R . . C25 C 0.1381(3) 0.3606(2) 0.4084(2) 0.0855(6) Uani 1 1 d . . . H25A H 0.0499 0.2854 0.3527 0.126(3) Uiso 1 1 calc R . . H25B H 0.1573 0.4341 0.3876 0.126(3) Uiso 1 1 calc R . . H25C H 0.1004 0.3861 0.4816 0.126(3) 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 0.1042(11) 0.0594(8) 0.0653(9) 0.0018(6) -0.0154(8) 0.0106(7) O2 0.1085(11) 0.0762(9) 0.0561(8) 0.0106(7) -0.0242(7) 0.0107(8) O3 0.0626(7) 0.0584(6) 0.0590(7) 0.0243(5) 0.0030(5) 0.0187(5) O4 0.0811(8) 0.0638(7) 0.0538(8) 0.0102(6) -0.0081(6) 0.0030(6) O5 0.0643(7) 0.0986(10) 0.0518(7) 0.0263(7) -0.0077(6) 0.0155(6) O6 0.0658(7) 0.0809(8) 0.0707(8) 0.0407(7) -0.0001(6) 0.0168(6) C1 0.0909(14) 0.0722(12) 0.0674(13) 0.0025(10) -0.0167(10) 0.0245(10) C2 0.0702(10) 0.0552(9) 0.0577(11) 0.0046(8) -0.0022(8) 0.0135(8) C3 0.0757(11) 0.0525(9) 0.0621(11) 0.0162(8) 0.0008(9) 0.0151(8) C4 0.0606(9) 0.0560(9) 0.0528(10) 0.0155(8) 0.0013(7) 0.0152(7) C5 0.0662(10) 0.0572(9) 0.0579(10) 0.0238(8) 0.0017(8) 0.0165(8) C6 0.0551(8) 0.0624(9) 0.0507(9) 0.0214(8) 0.0026(7) 0.0159(7) C7 0.0565(9) 0.0676(10) 0.0525(10) 0.0265(8) 0.0025(7) 0.0148(7) C8 0.0550(9) 0.0769(11) 0.0464(9) 0.0216(8) 0.0005(7) 0.0157(8) C9 0.0565(9) 0.0618(10) 0.0500(9) 0.0123(8) -0.0006(7) 0.0105(7) C10 0.0620(9) 0.0573(9) 0.0524(10) 0.0167(8) 0.0012(7) 0.0147(7) C11 0.0545(8) 0.0564(9) 0.0489(9) 0.0166(7) 0.0019(7) 0.0153(7) C12 0.0583(9) 0.0547(9) 0.0511(9) 0.0185(7) 0.0017(7) 0.0166(7) C13 0.0576(9) 0.0572(9) 0.0493(9) 0.0176(8) 0.0012(7) 0.0168(7) C14 0.0706(10) 0.0624(10) 0.0550(10) 0.0190(8) -0.0047(8) 0.0165(8) C15 0.0724(11) 0.0666(11) 0.0512(10) 0.0119(8) -0.0031(8) 0.0196(8) C16 0.0746(11) 0.0634(10) 0.0657(11) 0.0236(9) 0.0149(9) 0.0256(8) C17 0.0683(10) 0.0673(10) 0.0692(11) 0.0323(9) 0.0104(9) 0.0225(8) C18 0.143(2) 0.115(2) 0.0933(18) 0.0611(16) 0.0386(17) 0.0616(18) C19 0.148(3) 0.167(3) 0.155(3) 0.126(3) 0.055(3) 0.061(3) C20 0.1053(19) 0.100(2) 0.195(4) 0.094(2) 0.026(2) 0.0404(16) C21 0.0811(14) 0.0669(13) 0.142(2) 0.0389(14) 0.0082(14) 0.0265(10) C22 0.0744(11) 0.0646(11) 0.0852(14) 0.0286(10) 0.0062(10) 0.0241(9) C23 0.0933(14) 0.0636(11) 0.0679(13) 0.0148(10) 0.0015(11) 0.0026(10) C24 0.0922(15) 0.125(2) 0.0504(11) 0.0229(12) -0.0003(10) 0.0253(14) C25 0.0788(13) 0.0881(14) 0.1019(17) 0.0476(13) 0.0123(12) 0.0327(11) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 1.381(2) . ? O1 C1 1.425(3) . ? O2 C15 1.375(2) . ? O2 C1 1.390(3) . ? O3 C12 1.381(2) . ? O3 C16 1.437(2) . ? O4 C9 1.365(2) . ? O4 C23 1.416(3) . ? O5 C8 1.376(2) . ? O5 C24 1.400(3) . ? O6 C7 1.376(2) . ? O6 C25 1.421(2) . ? C1 H1A 0.9700 . ? C1 H1B 0.9700 . ? C2 C3 1.342(3) . ? C2 C15 1.402(3) . ? C3 C4 1.440(3) . ? C3 H3 0.9300 . ? C4 C5 1.392(3) . ? C4 C13 1.433(3) . ? C5 C6 1.389(3) . ? C5 H5 0.9300 . ? C6 C11 1.425(3) . ? C6 C7 1.434(2) . ? C7 C8 1.363(3) . ? C8 C9 1.425(3) . ? C9 C10 1.359(3) . ? C10 C11 1.421(2) . ? C10 H10 0.9300 . ? C11 C12 1.405(2) . ? C12 C13 1.395(2) . ? C13 C14 1.436(3) . ? C14 C15 1.336(3) . ? C14 H14 0.9300 . ? C16 C17 1.505(3) . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? C17 C18 1.347(3) . ? C17 C22 1.377(3) . ? C18 C19 1.393(4) . ? C18 H18 0.9300 . ? C19 C20 1.376(5) . ? C19 H19 0.9300 . ? C20 C21 1.340(4) . ? C20 H20 0.9300 . ? C21 C22 1.360(3) . ? C21 H21 0.9300 . ? C22 H22 0.9300 . ? C23 H23A 0.9600 . ? C23 H23B 0.9600 . ? C23 H23C 0.9600 . ? C24 H24A 0.9600 . ? C24 H24B 0.9600 . ? C24 H24C 0.9600 . ? C25 H25A 0.9600 . ? C25 H25B 0.9600 . ? C25 H25C 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 C1 105.55(16) . . ? C15 O2 C1 106.76(17) . . ? C12 O3 C16 113.60(13) . . ? C9 O4 C23 116.48(15) . . ? C8 O5 C24 116.20(15) . . ? C7 O6 C25 115.26(15) . . ? O2 C1 O1 109.60(16) . . ? O2 C1 H1A 109.8 . . ? O1 C1 H1A 109.8 . . ? O2 C1 H1B 109.8 . . ? O1 C1 H1B 109.8 . . ? H1A C1 H1B 108.2 . . ? C3 C2 O1 127.70(19) . . ? C3 C2 C15 123.32(17) . . ? O1 C2 C15 108.97(17) . . ? C2 C3 C4 117.13(18) . . ? C2 C3 H3 121.4 . . ? C4 C3 H3 121.4 . . ? C5 C4 C13 119.48(16) . . ? C5 C4 C3 121.29(17) . . ? C13 C4 C3 119.24(17) . . ? C6 C5 C4 121.79(17) . . ? C6 C5 H5 119.1 . . ? C4 C5 H5 119.1 . . ? C5 C6 C11 119.55(16) . . ? C5 C6 C7 122.41(17) . . ? C11 C6 C7 118.04(16) . . ? C8 C7 O6 121.30(16) . . ? C8 C7 C6 120.81(17) . . ? O6 C7 C6 117.85(16) . . ? C7 C8 O5 120.85(18) . . ? C7 C8 C9 120.15(16) . . ? O5 C8 C9 118.91(16) . . ? C10 C9 O4 124.76(18) . . ? C10 C9 C8 121.02(16) . . ? O4 C9 C8 114.22(16) . . ? C9 C10 C11 119.98(17) . . ? C9 C10 H10 120.0 . . ? C11 C10 H10 120.0 . . ? C12 C11 C10 121.43(17) . . ? C12 C11 C6 118.58(16) . . ? C10 C11 C6 119.99(16) . . ? O3 C12 C13 118.72(15) . . ? O3 C12 C11 119.05(15) . . ? C13 C12 C11 122.18(16) . . ? C12 C13 C4 118.40(16) . . ? C12 C13 C14 121.23(17) . . ? C4 C13 C14 120.36(16) . . ? C15 C14 C13 117.15(18) . . ? C15 C14 H14 121.4 . . ? C13 C14 H14 121.4 . . ? C14 C15 O2 128.12(19) . . ? C14 C15 C2 122.80(18) . . ? O2 C15 C2 109.08(16) . . ? O3 C16 C17 109.42(14) . . ? O3 C16 H16A 109.8 . . ? C17 C16 H16A 109.8 . . ? O3 C16 H16B 109.8 . . ? C17 C16 H16B 109.8 . . ? H16A C16 H16B 108.2 . . ? C18 C17 C22 117.3(2) . . ? C18 C17 C16 121.15(19) . . ? C22 C17 C16 121.33(18) . . ? C17 C18 C19 121.3(3) . . ? C17 C18 H18 119.4 . . ? C19 C18 H18 119.4 . . ? C20 C19 C18 119.7(3) . . ? C20 C19 H19 120.2 . . ? C18 C19 H19 120.2 . . ? C21 C20 C19 119.0(3) . . ? C21 C20 H20 120.5 . . ? C19 C20 H20 120.5 . . ? C20 C21 C22 120.6(3) . . ? C20 C21 H21 119.7 . . ? C22 C21 H21 119.7 . . ? C21 C22 C17 122.0(2) . . ? C21 C22 H22 119.0 . . ? C17 C22 H22 119.0 . . ? O4 C23 H23A 109.5 . . ? O4 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? O4 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? O5 C24 H24A 109.5 . . ? O5 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? O5 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? O6 C25 H25A 109.5 . . ? O6 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? O6 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 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 C15 O2 C1 O1 1.7(2) . . . . ? C2 O1 C1 O2 -1.9(2) . . . . ? C1 O1 C2 C3 -179.1(2) . . . . ? C1 O1 C2 C15 1.3(2) . . . . ? O1 C2 C3 C4 -179.68(18) . . . . ? C15 C2 C3 C4 -0.1(3) . . . . ? C2 C3 C4 C5 -179.70(17) . . . . ? C2 C3 C4 C13 0.1(3) . . . . ? C13 C4 C5 C6 1.4(3) . . . . ? C3 C4 C5 C6 -178.80(16) . . . . ? C4 C5 C6 C11 -2.0(3) . . . . ? C4 C5 C6 C7 177.79(16) . . . . ? C25 O6 C7 C8 72.2(2) . . . . ? C25 O6 C7 C6 -110.0(2) . . . . ? C5 C6 C7 C8 178.97(16) . . . . ? C11 C6 C7 C8 -1.2(3) . . . . ? C5 C6 C7 O6 1.2(3) . . . . ? C11 C6 C7 O6 -179.03(14) . . . . ? O6 C7 C8 O5 -5.1(3) . . . . ? C6 C7 C8 O5 177.18(15) . . . . ? O6 C7 C8 C9 178.44(15) . . . . ? C6 C7 C8 C9 0.7(3) . . . . ? C24 O5 C8 C7 90.8(2) . . . . ? C24 O5 C8 C9 -92.7(2) . . . . ? C23 O4 C9 C10 4.6(3) . . . . ? C23 O4 C9 C8 -175.33(16) . . . . ? C7 C8 C9 C10 -0.1(3) . . . . ? O5 C8 C9 C10 -176.61(15) . . . . ? C7 C8 C9 O4 179.84(15) . . . . ? O5 C8 C9 O4 3.3(2) . . . . ? O4 C9 C10 C11 -179.93(16) . . . . ? C8 C9 C10 C11 0.0(3) . . . . ? C9 C10 C11 C12 179.38(16) . . . . ? C9 C10 C11 C6 -0.5(3) . . . . ? C5 C6 C11 C12 1.0(3) . . . . ? C7 C6 C11 C12 -178.79(15) . . . . ? C5 C6 C11 C10 -179.06(15) . . . . ? C7 C6 C11 C10 1.1(2) . . . . ? C16 O3 C12 C13 94.90(18) . . . . ? C16 O3 C12 C11 -87.64(19) . . . . ? C10 C11 C12 O3 3.3(3) . . . . ? C6 C11 C12 O3 -176.76(14) . . . . ? C10 C11 C12 C13 -179.29(15) . . . . ? C6 C11 C12 C13 0.6(3) . . . . ? O3 C12 C13 C4 176.11(14) . . . . ? C11 C12 C13 C4 -1.3(3) . . . . ? O3 C12 C13 C14 -3.1(3) . . . . ? C11 C12 C13 C14 179.54(16) . . . . ? C5 C4 C13 C12 0.3(3) . . . . ? C3 C4 C13 C12 -179.55(16) . . . . ? C5 C4 C13 C14 179.50(16) . . . . ? C3 C4 C13 C14 -0.3(3) . . . . ? C12 C13 C14 C15 179.64(17) . . . . ? C4 C13 C14 C15 0.5(3) . . . . ? C13 C14 C15 O2 179.79(18) . . . . ? C13 C14 C15 C2 -0.4(3) . . . . ? C1 O2 C15 C14 178.9(2) . . . . ? C1 O2 C15 C2 -0.9(2) . . . . ? C3 C2 C15 C14 0.2(3) . . . . ? O1 C2 C15 C14 179.88(18) . . . . ? C3 C2 C15 O2 -179.95(19) . . . . ? O1 C2 C15 O2 -0.3(2) . . . . ? C12 O3 C16 C17 163.71(14) . . . . ? O3 C16 C17 C18 148.0(2) . . . . ? O3 C16 C17 C22 -37.9(2) . . . . ? C22 C17 C18 C19 0.6(4) . . . . ? C16 C17 C18 C19 174.9(3) . . . . ? C17 C18 C19 C20 2.3(5) . . . . ? C18 C19 C20 C21 -3.6(5) . . . . ? C19 C20 C21 C22 1.9(5) . . . . ? C20 C21 C22 C17 1.1(4) . . . . ? C18 C17 C22 C21 -2.3(3) . . . . ? C16 C17 C22 C21 -176.61(19) . . . . ? 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 C16 H16A O5 0.97 2.49 3.238(3) 134.2 2_556 C5 H5 O6 0.93 2.50 2.822(2) 100.4 . C25 H25A O5 0.96 2.49 3.066(3) 118.8 .