# Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_Cambridge 0177 _publ_contact_author_name 'Youhong Hu' _publ_contact_author_email YHHU@MAIL.SHCNC.AC.CN _publ_section_title ; A Base-Promoted Desalicyloylative Dimerization of 3-(1-Alkynyl)chromones: An Unusual Approach to 2-Alkynyl Xanthones ; loop_ _publ_author_name 'Youhong Hu.' 'Shijun Lin.' 'Xuan Pan.' 'Fuchun Xie.' # Attachment '3g1_cd29342.cif' data_cd29342 _database_code_depnum_ccdc_archive 'CCDC 747501' #TrackingRef '3g1_cd29342.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C21 H14 O4' _chemical_formula_weight 330.32 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 12.377(2) _cell_length_b 15.318(2) _cell_length_c 8.3322(14) _cell_angle_alpha 90.00 _cell_angle_beta 94.579(3) _cell_angle_gamma 90.00 _cell_volume 1574.6(4) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 1919 _cell_measurement_theta_min 5.319 _cell_measurement_theta_max 49.148 _exptl_crystal_description prismatic _exptl_crystal_colour colorless _exptl_crystal_size_max 0.403 _exptl_crystal_size_mid 0.347 _exptl_crystal_size_min 0.112 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.393 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 688 _exptl_absorpt_coefficient_mu 0.097 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.75675 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details sadabs _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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8210 _diffrn_reflns_av_R_equivalents 0.1184 _diffrn_reflns_av_sigmaI/netI 0.0840 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 2.12 _diffrn_reflns_theta_max 25.50 _reflns_number_total 2932 _reflns_number_gt 1814 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0517P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2932 _refine_ls_number_parameters 231 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0730 _refine_ls_R_factor_gt 0.0470 _refine_ls_wR_factor_ref 0.1152 _refine_ls_wR_factor_gt 0.1045 _refine_ls_goodness_of_fit_ref 0.877 _refine_ls_restrained_S_all 0.877 _refine_ls_shift/su_max 0.011 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.11523(10) 0.08830(12) 0.17278(16) 0.0885(5) Uani 1 1 d . . . O2 O -0.03009(11) 0.10741(13) 0.3780(2) 0.0950(6) Uani 1 1 d D . . O3 O 0.47072(12) 0.25136(11) -0.0370(2) 0.0973(5) Uani 1 1 d . . . O4 O 0.62249(9) 0.03559(8) 0.16481(13) 0.0568(3) Uani 1 1 d . . . C1 C 0.18672(14) 0.09363(13) 0.2833(2) 0.0572(5) Uani 1 1 d . . . C2 C 0.16244(13) 0.11806(11) 0.44630(19) 0.0494(4) Uani 1 1 d . . . C3 C 0.24426(14) 0.13755(12) 0.5652(2) 0.0543(5) Uani 1 1 d . . . H3 H 0.3161 0.1356 0.5403 0.065 Uiso 1 1 calc R . . C4 C 0.22130(16) 0.15953(13) 0.7183(2) 0.0660(5) Uani 1 1 d . . . H4 H 0.2770 0.1719 0.7966 0.079 Uiso 1 1 calc R . . C5 C 0.11498(17) 0.16311(14) 0.7548(2) 0.0733(6) Uani 1 1 d . . . H5 H 0.0989 0.1781 0.8584 0.088 Uiso 1 1 calc R . . C6 C 0.03264(16) 0.14497(14) 0.6406(2) 0.0751(6) Uani 1 1 d . . . H6 H -0.0388 0.1472 0.6673 0.090 Uiso 1 1 calc R . . C7 C 0.05475(14) 0.12349(13) 0.4863(2) 0.0617(5) Uani 1 1 d . . . C8 C 0.30260(13) 0.07664(12) 0.24948(18) 0.0501(4) Uani 1 1 d . . . C9 C 0.35256(14) 0.13369(12) 0.15270(19) 0.0542(5) Uani 1 1 d . . . H9 H 0.3131 0.1804 0.1072 0.065 Uiso 1 1 calc R . . C10 C 0.46075(13) 0.12402(11) 0.12008(19) 0.0497(4) Uani 1 1 d . . . C11 C 0.51556(13) 0.05168(11) 0.18617(18) 0.0470(4) Uani 1 1 d . . . C12 C 0.46544(13) -0.00803(12) 0.27965(19) 0.0522(4) Uani 1 1 d . . . H12 H 0.5038 -0.0565 0.3200 0.063 Uiso 1 1 calc R . . C13 C 0.35918(13) 0.00327(12) 0.31403(18) 0.0499(4) Uani 1 1 d . . . C14 C 0.51626(15) 0.18703(14) 0.0242(2) 0.0611(5) Uani 1 1 d . . . C15 C 0.63119(14) 0.16847(12) 0.00924(19) 0.0534(5) Uani 1 1 d . . . C16 C 0.69575(16) 0.22410(14) -0.0751(2) 0.0666(5) Uani 1 1 d . . . H16 H 0.6650 0.2734 -0.1255 0.080 Uiso 1 1 calc R . . C17 C 0.80385(17) 0.20710(16) -0.0848(2) 0.0767(6) Uani 1 1 d . . . H17 H 0.8465 0.2453 -0.1391 0.092 Uiso 1 1 calc R . . C18 C 0.84882(16) 0.13268(17) -0.0129(2) 0.0764(6) Uani 1 1 d . . . H18 H 0.9220 0.1209 -0.0202 0.092 Uiso 1 1 calc R . . C19 C 0.78738(14) 0.07611(15) 0.0687(2) 0.0659(6) Uani 1 1 d . . . H19 H 0.8180 0.0259 0.1159 0.079 Uiso 1 1 calc R . . C20 C 0.67915(13) 0.09497(13) 0.07947(18) 0.0513(4) Uani 1 1 d . . . C21 C 0.30684(15) -0.06332(13) 0.4149(2) 0.0669(5) Uani 1 1 d . . . H21A H 0.3505 -0.1152 0.4226 0.100 Uiso 1 1 calc R . . H21B H 0.2361 -0.0773 0.3660 0.100 Uiso 1 1 calc R . . H21C H 0.3004 -0.0401 0.5208 0.100 Uiso 1 1 calc R . . H2 H -0.0036(19) 0.0974(17) 0.287(2) 0.116(10) Uiso 1 1 d D . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0560(8) 0.1525(15) 0.0549(8) -0.0226(9) -0.0081(7) 0.0159(8) O2 0.0463(8) 0.1560(17) 0.0819(11) -0.0287(11) -0.0002(8) 0.0054(8) O3 0.0910(10) 0.0975(12) 0.1081(12) 0.0505(10) 0.0363(9) 0.0340(9) O4 0.0461(7) 0.0673(9) 0.0572(7) 0.0032(6) 0.0046(6) 0.0076(6) C1 0.0515(11) 0.0729(13) 0.0465(10) -0.0042(9) -0.0007(9) 0.0032(9) C2 0.0448(10) 0.0580(11) 0.0458(9) -0.0014(8) 0.0072(8) -0.0011(8) C3 0.0508(10) 0.0647(13) 0.0478(10) -0.0035(8) 0.0067(8) -0.0036(8) C4 0.0707(13) 0.0807(15) 0.0465(10) -0.0067(9) 0.0036(10) -0.0073(10) C5 0.0840(15) 0.0867(17) 0.0525(11) -0.0082(10) 0.0253(11) -0.0031(11) C6 0.0573(12) 0.1031(18) 0.0675(13) -0.0065(12) 0.0220(11) -0.0001(11) C7 0.0499(11) 0.0758(14) 0.0598(11) -0.0061(10) 0.0070(9) 0.0017(9) C8 0.0465(10) 0.0669(13) 0.0366(8) -0.0076(8) 0.0022(7) 0.0039(8) C9 0.0546(11) 0.0683(13) 0.0395(9) 0.0009(9) 0.0040(8) 0.0143(9) C10 0.0522(10) 0.0588(12) 0.0385(9) -0.0020(8) 0.0052(8) 0.0079(8) C11 0.0448(10) 0.0587(11) 0.0373(8) -0.0068(8) 0.0012(7) 0.0039(8) C12 0.0532(11) 0.0535(11) 0.0490(9) -0.0024(8) -0.0009(8) 0.0042(8) C13 0.0519(11) 0.0578(11) 0.0395(9) -0.0061(8) 0.0010(8) -0.0032(8) C14 0.0667(12) 0.0690(13) 0.0492(10) 0.0061(10) 0.0138(9) 0.0128(10) C15 0.0577(11) 0.0652(13) 0.0382(9) -0.0065(8) 0.0094(8) 0.0003(9) C16 0.0800(14) 0.0711(14) 0.0513(11) -0.0044(9) 0.0217(10) -0.0011(10) C17 0.0774(15) 0.0942(19) 0.0612(13) -0.0116(12) 0.0230(11) -0.0188(13) C18 0.0546(12) 0.112(2) 0.0630(12) -0.0054(13) 0.0110(10) -0.0078(12) C19 0.0507(12) 0.0899(16) 0.0569(11) -0.0027(10) 0.0026(9) 0.0025(10) C20 0.0488(10) 0.0655(13) 0.0400(9) -0.0078(8) 0.0054(8) -0.0039(9) C21 0.0644(12) 0.0691(14) 0.0674(12) 0.0010(10) 0.0065(10) -0.0077(10) _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 C1 1.2277(18) . ? O2 C7 1.351(2) . ? O2 H2 0.859(16) . ? O3 C14 1.226(2) . ? O4 C11 1.3717(19) . ? O4 C20 1.380(2) . ? C1 C2 1.463(2) . ? C1 C8 1.506(2) . ? C2 C3 1.392(2) . ? C2 C7 1.402(2) . ? C3 C4 1.371(2) . ? C3 H3 0.9300 . ? C4 C5 1.375(3) . ? C4 H4 0.9300 . ? C5 C6 1.366(3) . ? C5 H5 0.9300 . ? C6 C7 1.376(3) . ? C6 H6 0.9300 . ? C8 C9 1.370(2) . ? C8 C13 1.408(2) . ? C9 C10 1.395(2) . ? C9 H9 0.9300 . ? C10 C11 1.390(2) . ? C10 C14 1.459(3) . ? C11 C12 1.380(2) . ? C12 C13 1.379(2) . ? C12 H12 0.9300 . ? C13 C21 1.501(2) . ? C14 C15 1.466(2) . ? C15 C20 1.381(3) . ? C15 C16 1.396(3) . ? C16 C17 1.372(3) . ? C16 H16 0.9300 . ? C17 C18 1.384(3) . ? C17 H17 0.9300 . ? C18 C19 1.369(3) . ? C18 H18 0.9300 . ? C19 C20 1.380(2) . ? C19 H19 0.9300 . ? C21 H21A 0.9600 . ? C21 H21B 0.9600 . ? C21 H21C 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 C7 O2 H2 106.8(16) . . ? C11 O4 C20 118.93(14) . . ? O1 C1 C2 121.60(16) . . ? O1 C1 C8 119.24(15) . . ? C2 C1 C8 119.14(14) . . ? C3 C2 C7 118.02(16) . . ? C3 C2 C1 121.61(15) . . ? C7 C2 C1 120.36(15) . . ? C4 C3 C2 121.48(16) . . ? C4 C3 H3 119.3 . . ? C2 C3 H3 119.3 . . ? C3 C4 C5 119.24(18) . . ? C3 C4 H4 120.4 . . ? C5 C4 H4 120.4 . . ? C6 C5 C4 120.79(18) . . ? C6 C5 H5 119.6 . . ? C4 C5 H5 119.6 . . ? C5 C6 C7 120.43(18) . . ? C5 C6 H6 119.8 . . ? C7 C6 H6 119.8 . . ? O2 C7 C6 117.75(17) . . ? O2 C7 C2 122.24(17) . . ? C6 C7 C2 120.00(17) . . ? C9 C8 C13 120.00(16) . . ? C9 C8 C1 118.77(16) . . ? C13 C8 C1 121.23(16) . . ? C8 C9 C10 122.16(16) . . ? C8 C9 H9 118.9 . . ? C10 C9 H9 118.9 . . ? C11 C10 C9 116.94(16) . . ? C11 C10 C14 120.53(16) . . ? C9 C10 C14 122.52(16) . . ? O4 C11 C12 115.84(15) . . ? O4 C11 C10 122.50(16) . . ? C12 C11 C10 121.65(16) . . ? C13 C12 C11 120.87(16) . . ? C13 C12 H12 119.6 . . ? C11 C12 H12 119.6 . . ? C12 C13 C8 118.31(16) . . ? C12 C13 C21 119.50(16) . . ? C8 C13 C21 122.17(16) . . ? O3 C14 C10 122.56(17) . . ? O3 C14 C15 122.54(18) . . ? C10 C14 C15 114.89(16) . . ? C20 C15 C16 117.85(17) . . ? C20 C15 C14 120.62(17) . . ? C16 C15 C14 121.53(18) . . ? C17 C16 C15 120.9(2) . . ? C17 C16 H16 119.5 . . ? C15 C16 H16 119.5 . . ? C16 C17 C18 119.4(2) . . ? C16 C17 H17 120.3 . . ? C18 C17 H17 120.3 . . ? C19 C18 C17 121.1(2) . . ? C19 C18 H18 119.5 . . ? C17 C18 H18 119.5 . . ? C18 C19 C20 118.7(2) . . ? C18 C19 H19 120.6 . . ? C20 C19 H19 120.6 . . ? O4 C20 C19 115.56(17) . . ? O4 C20 C15 122.47(15) . . ? C19 C20 C15 121.97(17) . . ? C13 C21 H21A 109.5 . . ? C13 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C13 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 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 O1 C1 C2 C3 -169.68(18) . . . . ? C8 C1 C2 C3 8.9(3) . . . . ? O1 C1 C2 C7 9.5(3) . . . . ? C8 C1 C2 C7 -171.91(17) . . . . ? C7 C2 C3 C4 1.5(3) . . . . ? C1 C2 C3 C4 -179.30(19) . . . . ? C2 C3 C4 C5 -0.6(3) . . . . ? C3 C4 C5 C6 0.1(3) . . . . ? C4 C5 C6 C7 -0.6(3) . . . . ? C5 C6 C7 O2 -179.10(19) . . . . ? C5 C6 C7 C2 1.5(3) . . . . ? C3 C2 C7 O2 178.71(18) . . . . ? C1 C2 C7 O2 -0.5(3) . . . . ? C3 C2 C7 C6 -1.9(3) . . . . ? C1 C2 C7 C6 178.83(19) . . . . ? O1 C1 C8 C9 66.8(2) . . . . ? C2 C1 C8 C9 -111.85(19) . . . . ? O1 C1 C8 C13 -112.6(2) . . . . ? C2 C1 C8 C13 68.8(2) . . . . ? C13 C8 C9 C10 -2.8(2) . . . . ? C1 C8 C9 C10 177.85(15) . . . . ? C8 C9 C10 C11 2.1(2) . . . . ? C8 C9 C10 C14 -176.64(16) . . . . ? C20 O4 C11 C12 -176.77(13) . . . . ? C20 O4 C11 C10 2.4(2) . . . . ? C9 C10 C11 O4 -179.05(14) . . . . ? C14 C10 C11 O4 -0.3(2) . . . . ? C9 C10 C11 C12 0.1(2) . . . . ? C14 C10 C11 C12 178.84(15) . . . . ? O4 C11 C12 C13 177.64(14) . . . . ? C10 C11 C12 C13 -1.6(2) . . . . ? C11 C12 C13 C8 0.9(2) . . . . ? C11 C12 C13 C21 179.49(15) . . . . ? C9 C8 C13 C12 1.2(2) . . . . ? C1 C8 C13 C12 -179.41(15) . . . . ? C9 C8 C13 C21 -177.33(15) . . . . ? C1 C8 C13 C21 2.0(2) . . . . ? C11 C10 C14 O3 179.55(18) . . . . ? C9 C10 C14 O3 -1.8(3) . . . . ? C11 C10 C14 C15 -1.6(2) . . . . ? C9 C10 C14 C15 177.08(15) . . . . ? O3 C14 C15 C20 -179.69(19) . . . . ? C10 C14 C15 C20 1.5(2) . . . . ? O3 C14 C15 C16 0.6(3) . . . . ? C10 C14 C15 C16 -178.24(16) . . . . ? C20 C15 C16 C17 -1.4(3) . . . . ? C14 C15 C16 C17 178.36(17) . . . . ? C15 C16 C17 C18 1.5(3) . . . . ? C16 C17 C18 C19 -0.5(3) . . . . ? C17 C18 C19 C20 -0.5(3) . . . . ? C11 O4 C20 C19 177.46(14) . . . . ? C11 O4 C20 C15 -2.6(2) . . . . ? C18 C19 C20 O4 -179.36(15) . . . . ? C18 C19 C20 C15 0.7(3) . . . . ? C16 C15 C20 O4 -179.70(14) . . . . ? C14 C15 C20 O4 0.6(2) . . . . ? C16 C15 C20 C19 0.3(3) . . . . ? C14 C15 C20 C19 -179.45(16) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.184 _refine_diff_density_min -0.188 _refine_diff_density_rms 0.045 # Attachment '2b_cd29355.cif' data_cd29355 _database_code_depnum_ccdc_archive 'CCDC 747502' #TrackingRef '2b_cd29355.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C29 H20 O4' _chemical_formula_weight 432.45 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 6.3113(6) _cell_length_b 8.5733(9) _cell_length_c 39.914(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2159.7(4) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 2069 _cell_measurement_theta_min 4.860 _cell_measurement_theta_max 42.579 _exptl_crystal_description prismatic _exptl_crystal_colour green _exptl_crystal_size_max 0.307 _exptl_crystal_size_mid 0.215 _exptl_crystal_size_min 0.076 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.330 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 904 _exptl_absorpt_coefficient_mu 0.088 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.8109 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details sadabs _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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11925 _diffrn_reflns_av_R_equivalents 0.0593 _diffrn_reflns_av_sigmaI/netI 0.0540 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -44 _diffrn_reflns_limit_l_max 49 _diffrn_reflns_theta_min 2.04 _diffrn_reflns_theta_max 26.00 _reflns_number_total 2469 _reflns_number_gt 1640 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0251P)^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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 10(10) _chemical_absolute_configuration unknown _refine_ls_number_reflns 2469 _refine_ls_number_parameters 300 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0547 _refine_ls_R_factor_gt 0.0334 _refine_ls_wR_factor_ref 0.0623 _refine_ls_wR_factor_gt 0.0587 _refine_ls_goodness_of_fit_ref 0.832 _refine_ls_restrained_S_all 0.832 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O -0.0679(3) 1.2999(2) 0.17202(4) 0.0745(6) Uani 1 1 d . . . O2 O -0.2232(2) 1.03306(16) 0.09064(4) 0.0459(4) Uani 1 1 d . . . O3 O -0.1735(3) 0.44989(19) -0.00314(4) 0.0662(5) Uani 1 1 d . . . O4 O 1.4148(3) 0.66696(19) 0.24127(4) 0.0654(5) Uani 1 1 d . . . C1 C -0.1131(4) 1.2224(3) 0.14733(6) 0.0495(6) Uani 1 1 d . . . C2 C -0.3025(4) 1.2523(3) 0.12713(5) 0.0437(6) Uani 1 1 d . . . C3 C -0.4428(4) 1.3730(3) 0.13466(6) 0.0544(7) Uani 1 1 d . . . H3 H -0.4160 1.4373 0.1530 0.065 Uiso 1 1 calc R . . C4 C -0.6199(4) 1.3983(3) 0.11541(7) 0.0583(7) Uani 1 1 d . . . H4 H -0.7129 1.4786 0.1208 0.070 Uiso 1 1 calc R . . C5 C -0.6598(4) 1.3038(3) 0.08789(6) 0.0566(7) Uani 1 1 d . . . H5 H -0.7791 1.3218 0.0748 0.068 Uiso 1 1 calc R . . C6 C -0.5244(4) 1.1836(3) 0.07987(5) 0.0494(6) Uani 1 1 d . . . H6 H -0.5511 1.1204 0.0614 0.059 Uiso 1 1 calc R . . C7 C -0.3478(4) 1.1582(2) 0.09974(5) 0.0410(6) Uani 1 1 d . . . C8 C -0.0445(3) 0.9998(3) 0.10900(5) 0.0398(6) Uani 1 1 d . . . C9 C 0.0180(4) 1.0908(2) 0.13604(6) 0.0412(6) Uani 1 1 d . . . C10 C 0.2047(4) 1.0531(3) 0.15294(6) 0.0479(6) Uani 1 1 d . . . H10 H 0.2464 1.1130 0.1712 0.057 Uiso 1 1 calc R . . C11 C 0.3285(4) 0.9291(3) 0.14308(6) 0.0465(6) Uani 1 1 d . . . C12 C 0.2590(4) 0.8403(3) 0.11577(6) 0.0474(6) Uani 1 1 d . . . H12 H 0.3422 0.7568 0.1088 0.057 Uiso 1 1 calc R . . C13 C 0.0739(3) 0.8700(3) 0.09872(5) 0.0422(6) Uani 1 1 d . . . C14 C 0.0024(4) 0.7633(2) 0.07149(5) 0.0428(6) Uani 1 1 d . . . C15 C 0.1322(4) 0.7288(3) 0.04457(6) 0.0536(7) Uani 1 1 d . . . H15 H 0.2645 0.7758 0.0429 0.064 Uiso 1 1 calc R . . C16 C 0.0675(4) 0.6251(3) 0.02007(6) 0.0579(7) Uani 1 1 d . . . H16 H 0.1550 0.6058 0.0018 0.069 Uiso 1 1 calc R . . C17 C -0.1240(4) 0.5506(3) 0.02242(6) 0.0500(6) Uani 1 1 d . . . C18 C -0.2545(4) 0.5823(3) 0.04916(6) 0.0634(8) Uani 1 1 d . . . H18 H -0.3849 0.5326 0.0511 0.076 Uiso 1 1 calc R . . C19 C -0.1903(4) 0.6889(3) 0.07320(6) 0.0610(7) Uani 1 1 d . . . H19 H -0.2802 0.7108 0.0910 0.073 Uiso 1 1 calc R . . C20 C 0.5199(4) 0.8886(3) 0.16063(6) 0.0514(7) Uani 1 1 d . . . C21 C 0.6767(4) 0.8527(3) 0.17538(6) 0.0525(6) Uani 1 1 d . . . C22 C 0.8650(4) 0.8087(3) 0.19298(5) 0.0466(6) Uani 1 1 d . . . C23 C 0.9507(4) 0.8999(3) 0.21805(6) 0.0564(7) Uani 1 1 d . . . H23 H 0.8840 0.9930 0.2237 0.068 Uiso 1 1 calc R . . C24 C 1.1316(4) 0.8577(3) 0.23498(6) 0.0548(7) Uani 1 1 d . . . H24 H 1.1849 0.9209 0.2519 0.066 Uiso 1 1 calc R . . C25 C 1.2331(4) 0.7208(3) 0.22660(6) 0.0480(6) Uani 1 1 d . . . C26 C 1.1500(4) 0.6275(3) 0.20171(6) 0.0560(7) Uani 1 1 d . . . H26 H 1.2177 0.5348 0.1961 0.067 Uiso 1 1 calc R . . C27 C 0.9684(4) 0.6700(3) 0.18519(6) 0.0536(7) Uani 1 1 d . . . H27 H 0.9138 0.6054 0.1686 0.064 Uiso 1 1 calc R . . C28 C -0.3748(5) 0.3788(3) -0.00287(7) 0.0977(11) Uani 1 1 d . . . H28A H -0.3861 0.3115 0.0163 0.147 Uiso 1 1 calc R . . H28B H -0.3929 0.3188 -0.0230 0.147 Uiso 1 1 calc R . . H28C H -0.4824 0.4578 -0.0017 0.147 Uiso 1 1 calc R . . C29 C 1.5089(5) 0.7591(3) 0.26684(6) 0.0778(9) Uani 1 1 d . . . H29A H 1.5305 0.8632 0.2587 0.117 Uiso 1 1 calc R . . H29B H 1.6427 0.7145 0.2731 0.117 Uiso 1 1 calc R . . H29C H 1.4170 0.7617 0.2860 0.117 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 0.0753(14) 0.0686(12) 0.0797(13) -0.0327(10) -0.0200(11) 0.0067(11) O2 0.0420(10) 0.0446(9) 0.0511(10) -0.0042(8) -0.0060(8) 0.0045(8) O3 0.0729(13) 0.0617(11) 0.0639(11) -0.0226(9) 0.0093(10) -0.0071(11) O4 0.0604(13) 0.0597(11) 0.0762(12) 0.0082(9) -0.0236(10) 0.0028(10) C1 0.0522(17) 0.0416(15) 0.0548(15) -0.0050(12) -0.0025(14) -0.0048(13) C2 0.0444(15) 0.0353(13) 0.0514(15) -0.0003(11) 0.0017(12) -0.0027(12) C3 0.0545(17) 0.0388(14) 0.0699(17) -0.0050(13) 0.0062(15) -0.0050(14) C4 0.0535(18) 0.0414(15) 0.0801(19) 0.0096(14) 0.0099(16) 0.0029(14) C5 0.0486(17) 0.0541(16) 0.0671(17) 0.0122(14) -0.0033(15) 0.0010(15) C6 0.0502(16) 0.0482(15) 0.0497(15) 0.0051(12) -0.0029(13) 0.0020(14) C7 0.0388(14) 0.0355(13) 0.0487(14) 0.0057(11) 0.0034(12) 0.0021(13) C8 0.0345(14) 0.0423(14) 0.0427(14) 0.0068(11) -0.0021(11) -0.0024(12) C9 0.0403(15) 0.0380(14) 0.0452(14) 0.0023(11) -0.0018(12) -0.0059(12) C10 0.0441(16) 0.0507(15) 0.0488(15) 0.0029(12) -0.0033(13) -0.0103(14) C11 0.0376(15) 0.0457(15) 0.0562(15) 0.0082(13) -0.0012(13) -0.0026(13) C12 0.0396(15) 0.0393(14) 0.0632(16) 0.0043(13) 0.0046(13) 0.0005(13) C13 0.0397(14) 0.0385(13) 0.0484(14) 0.0023(11) 0.0017(12) -0.0034(12) C14 0.0411(15) 0.0376(13) 0.0496(14) -0.0005(11) 0.0049(12) 0.0001(12) C15 0.0429(16) 0.0598(16) 0.0581(16) -0.0055(13) 0.0091(13) -0.0056(14) C16 0.0546(18) 0.0642(17) 0.0549(16) -0.0088(14) 0.0161(13) 0.0012(16) C17 0.0583(18) 0.0416(14) 0.0502(15) -0.0089(13) 0.0069(14) -0.0028(14) C18 0.0607(19) 0.0597(17) 0.0698(18) -0.0193(15) 0.0199(15) -0.0171(14) C19 0.0567(19) 0.0632(17) 0.0630(17) -0.0203(14) 0.0211(14) -0.0127(15) C20 0.0392(17) 0.0548(17) 0.0603(16) 0.0114(13) 0.0018(14) -0.0038(14) C21 0.0427(16) 0.0559(16) 0.0591(16) 0.0103(13) 0.0020(14) -0.0048(15) C22 0.0417(15) 0.0497(16) 0.0483(14) 0.0103(12) -0.0004(12) -0.0016(14) C23 0.0554(18) 0.0568(17) 0.0570(16) -0.0042(14) 0.0001(14) 0.0126(14) C24 0.0585(18) 0.0545(16) 0.0515(15) -0.0053(13) -0.0080(14) 0.0000(16) C25 0.0444(16) 0.0471(15) 0.0525(15) 0.0107(13) -0.0048(13) -0.0013(14) C26 0.0581(18) 0.0413(14) 0.0687(17) -0.0015(13) -0.0078(15) 0.0024(14) C27 0.0537(18) 0.0464(16) 0.0608(16) 0.0017(13) -0.0145(14) -0.0064(14) C28 0.099(3) 0.104(2) 0.090(2) -0.0419(19) 0.021(2) -0.049(2) C29 0.069(2) 0.095(2) 0.0694(19) 0.0071(17) -0.0285(16) -0.0107(18) _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 C1 1.222(2) . ? O2 C8 1.375(2) . ? O2 C7 1.379(2) . ? O3 C17 1.373(3) . ? O3 C28 1.409(3) . ? O4 C25 1.368(3) . ? O4 C29 1.420(3) . ? C1 C2 1.465(3) . ? C1 C9 1.470(3) . ? C2 C7 1.389(3) . ? C2 C3 1.394(3) . ? C3 C4 1.374(3) . ? C3 H3 0.9300 . ? C4 C5 1.388(3) . ? C4 H4 0.9300 . ? C5 C6 1.377(3) . ? C5 H5 0.9300 . ? C6 C7 1.385(3) . ? C6 H6 0.9300 . ? C8 C9 1.389(3) . ? C8 C13 1.402(3) . ? C9 C10 1.396(3) . ? C10 C11 1.377(3) . ? C10 H10 0.9300 . ? C11 C12 1.400(3) . ? C11 C20 1.439(3) . ? C12 C13 1.376(3) . ? C12 H12 0.9300 . ? C13 C14 1.491(3) . ? C14 C19 1.374(3) . ? C14 C15 1.383(3) . ? C15 C16 1.383(3) . ? C15 H15 0.9300 . ? C16 C17 1.370(3) . ? C16 H16 0.9300 . ? C17 C18 1.375(3) . ? C18 C19 1.385(3) . ? C18 H18 0.9300 . ? C19 H19 0.9300 . ? C20 C21 1.192(3) . ? C21 C22 1.431(3) . ? C22 C23 1.380(3) . ? C22 C27 1.391(3) . ? C23 C24 1.375(3) . ? C23 H23 0.9300 . ? C24 C25 1.378(3) . ? C24 H24 0.9300 . ? C25 C26 1.379(3) . ? C26 C27 1.371(3) . ? C26 H26 0.9300 . ? C27 H27 0.9300 . ? C28 H28A 0.9600 . ? C28 H28B 0.9600 . ? C28 H28C 0.9600 . ? C29 H29A 0.9600 . ? C29 H29B 0.9600 . ? C29 H29C 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 C8 O2 C7 119.27(17) . . ? C17 O3 C28 118.2(2) . . ? C25 O4 C29 118.0(2) . . ? O1 C1 C2 122.6(2) . . ? O1 C1 C9 122.2(2) . . ? C2 C1 C9 115.2(2) . . ? C7 C2 C3 118.1(2) . . ? C7 C2 C1 119.9(2) . . ? C3 C2 C1 122.0(2) . . ? C4 C3 C2 120.9(2) . . ? C4 C3 H3 119.6 . . ? C2 C3 H3 119.6 . . ? C3 C4 C5 119.9(2) . . ? C3 C4 H4 120.1 . . ? C5 C4 H4 120.1 . . ? C6 C5 C4 120.6(2) . . ? C6 C5 H5 119.7 . . ? C4 C5 H5 119.7 . . ? C5 C6 C7 118.9(2) . . ? C5 C6 H6 120.5 . . ? C7 C6 H6 120.5 . . ? O2 C7 C6 115.5(2) . . ? O2 C7 C2 122.8(2) . . ? C6 C7 C2 121.7(2) . . ? O2 C8 C9 122.0(2) . . ? O2 C8 C13 116.50(19) . . ? C9 C8 C13 121.5(2) . . ? C8 C9 C10 119.0(2) . . ? C8 C9 C1 120.6(2) . . ? C10 C9 C1 120.3(2) . . ? C11 C10 C9 121.3(2) . . ? C11 C10 H10 119.4 . . ? C9 C10 H10 119.4 . . ? C10 C11 C12 117.7(2) . . ? C10 C11 C20 121.6(2) . . ? C12 C11 C20 120.7(2) . . ? C13 C12 C11 123.4(2) . . ? C13 C12 H12 118.3 . . ? C11 C12 H12 118.3 . . ? C12 C13 C8 117.1(2) . . ? C12 C13 C14 120.3(2) . . ? C8 C13 C14 122.6(2) . . ? C19 C14 C15 117.6(2) . . ? C19 C14 C13 121.1(2) . . ? C15 C14 C13 121.2(2) . . ? C16 C15 C14 120.8(2) . . ? C16 C15 H15 119.6 . . ? C14 C15 H15 119.6 . . ? C17 C16 C15 120.7(2) . . ? C17 C16 H16 119.6 . . ? C15 C16 H16 119.6 . . ? C16 C17 O3 116.3(2) . . ? C16 C17 C18 119.3(2) . . ? O3 C17 C18 124.4(2) . . ? C17 C18 C19 119.5(2) . . ? C17 C18 H18 120.2 . . ? C19 C18 H18 120.2 . . ? C14 C19 C18 122.0(2) . . ? C14 C19 H19 119.0 . . ? C18 C19 H19 119.0 . . ? C21 C20 C11 178.8(3) . . ? C20 C21 C22 179.6(3) . . ? C23 C22 C27 117.5(2) . . ? C23 C22 C21 122.1(2) . . ? C27 C22 C21 120.3(2) . . ? C24 C23 C22 122.2(2) . . ? C24 C23 H23 118.9 . . ? C22 C23 H23 118.9 . . ? C23 C24 C25 119.4(2) . . ? C23 C24 H24 120.3 . . ? C25 C24 H24 120.3 . . ? O4 C25 C24 125.0(2) . . ? O4 C25 C26 115.6(2) . . ? C24 C25 C26 119.5(2) . . ? C27 C26 C25 120.7(2) . . ? C27 C26 H26 119.7 . . ? C25 C26 H26 119.7 . . ? C26 C27 C22 120.8(2) . . ? C26 C27 H27 119.6 . . ? C22 C27 H27 119.6 . . ? O3 C28 H28A 109.5 . . ? O3 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? O3 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? O4 C29 H29A 109.5 . . ? O4 C29 H29B 109.5 . . ? H29A C29 H29B 109.5 . . ? O4 C29 H29C 109.5 . . ? H29A C29 H29C 109.5 . . ? H29B C29 H29C 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 O1 C1 C2 C7 -178.7(2) . . . . ? C9 C1 C2 C7 0.6(3) . . . . ? O1 C1 C2 C3 0.7(4) . . . . ? C9 C1 C2 C3 179.98(19) . . . . ? C7 C2 C3 C4 -0.3(3) . . . . ? C1 C2 C3 C4 -179.7(2) . . . . ? C2 C3 C4 C5 -0.6(3) . . . . ? C3 C4 C5 C6 0.7(3) . . . . ? C4 C5 C6 C7 0.1(3) . . . . ? C8 O2 C7 C6 179.89(17) . . . . ? C8 O2 C7 C2 -0.9(3) . . . . ? C5 C6 C7 O2 178.24(19) . . . . ? C5 C6 C7 C2 -1.0(3) . . . . ? C3 C2 C7 O2 -178.11(19) . . . . ? C1 C2 C7 O2 1.3(3) . . . . ? C3 C2 C7 C6 1.1(3) . . . . ? C1 C2 C7 C6 -179.5(2) . . . . ? C7 O2 C8 C9 -1.6(3) . . . . ? C7 O2 C8 C13 179.28(18) . . . . ? O2 C8 C9 C10 -178.05(18) . . . . ? C13 C8 C9 C10 1.0(3) . . . . ? O2 C8 C9 C1 3.6(3) . . . . ? C13 C8 C9 C1 -177.4(2) . . . . ? O1 C1 C9 C8 176.4(2) . . . . ? C2 C1 C9 C8 -2.9(3) . . . . ? O1 C1 C9 C10 -2.0(3) . . . . ? C2 C1 C9 C10 178.72(19) . . . . ? C8 C9 C10 C11 0.7(3) . . . . ? C1 C9 C10 C11 179.10(19) . . . . ? C9 C10 C11 C12 -0.9(3) . . . . ? C9 C10 C11 C20 -179.3(2) . . . . ? C10 C11 C12 C13 -0.6(3) . . . . ? C20 C11 C12 C13 177.8(2) . . . . ? C11 C12 C13 C8 2.2(3) . . . . ? C11 C12 C13 C14 -175.5(2) . . . . ? O2 C8 C13 C12 176.69(17) . . . . ? C9 C8 C13 C12 -2.4(3) . . . . ? O2 C8 C13 C14 -5.7(3) . . . . ? C9 C8 C13 C14 175.2(2) . . . . ? C12 C13 C14 C19 120.9(2) . . . . ? C8 C13 C14 C19 -56.7(3) . . . . ? C12 C13 C14 C15 -55.4(3) . . . . ? C8 C13 C14 C15 127.0(2) . . . . ? C19 C14 C15 C16 1.1(3) . . . . ? C13 C14 C15 C16 177.6(2) . . . . ? C14 C15 C16 C17 -2.0(4) . . . . ? C15 C16 C17 O3 -179.9(2) . . . . ? C15 C16 C17 C18 1.4(4) . . . . ? C28 O3 C17 C16 -175.8(2) . . . . ? C28 O3 C17 C18 2.8(4) . . . . ? C16 C17 C18 C19 0.0(4) . . . . ? O3 C17 C18 C19 -178.6(2) . . . . ? C15 C14 C19 C18 0.3(4) . . . . ? C13 C14 C19 C18 -176.2(2) . . . . ? C17 C18 C19 C14 -0.9(4) . . . . ? C10 C11 C20 C21 109(15) . . . . ? C12 C11 C20 C21 -69(15) . . . . ? C11 C20 C21 C22 60(51) . . . . ? C20 C21 C22 C23 -177(100) . . . . ? C20 C21 C22 C27 3(45) . . . . ? C27 C22 C23 C24 0.1(4) . . . . ? C21 C22 C23 C24 180.0(2) . . . . ? C22 C23 C24 C25 0.7(4) . . . . ? C29 O4 C25 C24 -0.8(3) . . . . ? C29 O4 C25 C26 179.4(2) . . . . ? C23 C24 C25 O4 179.3(2) . . . . ? C23 C24 C25 C26 -0.9(3) . . . . ? O4 C25 C26 C27 -179.8(2) . . . . ? C24 C25 C26 C27 0.3(4) . . . . ? C25 C26 C27 C22 0.5(4) . . . . ? C23 C22 C27 C26 -0.7(3) . . . . ? C21 C22 C27 C26 179.4(2) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A C29 H29A O4 0.96 2.63 3.545(3) 160.2 3_855 C6 H6 O3 0.93 2.52 3.402(3) 157.6 4_465 _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 0.130 _refine_diff_density_min -0.125 _refine_diff_density_rms 0.027 # Attachment '3a_cd29412.cif' data_cd29412 _database_code_depnum_ccdc_archive 'CCDC 747503' #TrackingRef '3a_cd29412.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C26 H16 O4' _chemical_formula_weight 392.39 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 Orthorhombic _symmetry_space_group_name_H-M Pbca loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 14.460(2) _cell_length_b 7.7990(12) _cell_length_c 33.363(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3762.6(10) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 2740 _cell_measurement_theta_min 4.884 _cell_measurement_theta_max 47.810 _exptl_crystal_description prismatic _exptl_crystal_colour green _exptl_crystal_size_max 0.309 _exptl_crystal_size_mid 0.147 _exptl_crystal_size_min 0.112 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.385 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1632 _exptl_absorpt_coefficient_mu 0.093 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.7851 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details sadabs _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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 18529 _diffrn_reflns_av_R_equivalents 0.1148 _diffrn_reflns_av_sigmaI/netI 0.0807 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -40 _diffrn_reflns_limit_l_max 38 _diffrn_reflns_theta_min 1.86 _diffrn_reflns_theta_max 25.50 _reflns_number_total 3506 _reflns_number_gt 2087 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0726P)^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 SHELXL _refine_ls_extinction_coef 0.0039(7) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3506 _refine_ls_number_parameters 273 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0880 _refine_ls_R_factor_gt 0.0581 _refine_ls_wR_factor_ref 0.1509 _refine_ls_wR_factor_gt 0.1375 _refine_ls_goodness_of_fit_ref 0.891 _refine_ls_restrained_S_all 0.891 _refine_ls_shift/su_max 0.008 _refine_ls_shift/su_mean 0.001 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.70123(11) 0.4184(3) 0.53950(5) 0.0780(6) Uani 1 1 d . . . O2 O 0.96349(10) 0.2371(2) 0.55656(4) 0.0545(5) Uani 1 1 d . . . O3 O 0.79026(11) 0.3920(2) 0.72214(5) 0.0684(5) Uani 1 1 d . . . O4 O 0.64246(12) 0.4868(3) 0.75659(6) 0.0754(6) Uani 1 1 d . . . H4 H 0.6979 0.4893 0.7515 0.113 Uiso 1 1 calc R . . C1 C 0.78099(16) 0.3682(3) 0.54450(7) 0.0552(6) Uani 1 1 d . . . C2 C 0.84776(16) 0.3530(3) 0.51177(7) 0.0566(6) Uani 1 1 d . . . C3 C 0.82730(19) 0.4063(4) 0.47292(8) 0.0761(9) Uani 1 1 d . . . H3 H 0.7692 0.4513 0.4672 0.091 Uiso 1 1 calc R . . C4 C 0.8915(2) 0.3931(5) 0.44321(8) 0.0857(10) Uani 1 1 d . . . H4A H 0.8775 0.4307 0.4175 0.103 Uiso 1 1 calc R . . C5 C 0.9777(2) 0.3236(4) 0.45141(8) 0.0769(9) Uani 1 1 d . . . H5 H 1.0209 0.3143 0.4309 0.092 Uiso 1 1 calc R . . C6 C 1.00019(18) 0.2687(4) 0.48889(7) 0.0640(7) Uani 1 1 d . . . H6 H 1.0577 0.2201 0.4941 0.077 Uiso 1 1 calc R . . C7 C 0.93529(15) 0.2872(3) 0.51917(7) 0.0521(6) Uani 1 1 d . . . C8 C 0.90654(14) 0.2588(3) 0.58869(7) 0.0460(6) Uani 1 1 d . . . C9 C 0.81681(14) 0.3212(3) 0.58416(7) 0.0465(6) Uani 1 1 d . . . C10 C 0.76181(14) 0.3414(3) 0.61812(6) 0.0475(6) Uani 1 1 d . . . H10 H 0.7016 0.3817 0.6155 0.057 Uiso 1 1 calc R . . C11 C 0.79571(13) 0.3025(3) 0.65548(6) 0.0449(6) Uani 1 1 d . . . C12 C 0.88691(13) 0.2439(3) 0.65885(7) 0.0453(6) Uani 1 1 d . . . H12 H 0.9099 0.2199 0.6843 0.054 Uiso 1 1 calc R . . C13 C 0.94428(14) 0.2202(3) 0.62627(6) 0.0436(5) Uani 1 1 d . . . C14 C 1.04168(14) 0.1628(3) 0.63261(7) 0.0462(6) Uani 1 1 d . . . C15 C 1.08973(15) 0.2239(3) 0.66548(7) 0.0535(6) Uani 1 1 d . . . H15 H 1.0619 0.3040 0.6823 0.064 Uiso 1 1 calc R . . C16 C 1.17822(16) 0.1683(3) 0.67380(9) 0.0654(8) Uani 1 1 d . . . H16 H 1.2091 0.2092 0.6963 0.078 Uiso 1 1 calc R . . C17 C 1.22017(17) 0.0541(4) 0.64923(10) 0.0704(8) Uani 1 1 d . . . H17 H 1.2801 0.0178 0.6548 0.084 Uiso 1 1 calc R . . C18 C 1.17492(18) -0.0086(4) 0.61611(9) 0.0690(8) Uani 1 1 d . . . H18 H 1.2040 -0.0874 0.5994 0.083 Uiso 1 1 calc R . . C19 C 1.08512(16) 0.0466(3) 0.60764(8) 0.0585(7) Uani 1 1 d . . . H19 H 1.0545 0.0050 0.5851 0.070 Uiso 1 1 calc R . . C20 C 0.74486(15) 0.3385(3) 0.69324(7) 0.0480(6) Uani 1 1 d . . . C21 C 0.64461(14) 0.3178(3) 0.69623(6) 0.0449(6) Uani 1 1 d . . . C22 C 0.59303(15) 0.2224(3) 0.66890(7) 0.0535(6) Uani 1 1 d . . . H22 H 0.6230 0.1656 0.6481 0.064 Uiso 1 1 calc R . . C23 C 0.49882(17) 0.2110(4) 0.67222(8) 0.0652(7) Uani 1 1 d . . . H23 H 0.4651 0.1450 0.6542 0.078 Uiso 1 1 calc R . . C24 C 0.45446(17) 0.2982(4) 0.70259(9) 0.0696(8) Uani 1 1 d . . . H24 H 0.3903 0.2941 0.7041 0.083 Uiso 1 1 calc R . . C25 C 0.50236(17) 0.3903(4) 0.73041(8) 0.0661(7) Uani 1 1 d . . . H25 H 0.4712 0.4470 0.7509 0.079 Uiso 1 1 calc R . . C26 C 0.59789(16) 0.3986(3) 0.72790(7) 0.0533(6) 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 O1 0.0467(11) 0.1288(17) 0.0585(11) 0.0068(11) -0.0097(8) 0.0146(10) O2 0.0418(9) 0.0751(12) 0.0465(10) -0.0004(8) 0.0055(7) 0.0036(7) O3 0.0451(10) 0.1083(15) 0.0517(10) -0.0152(10) -0.0021(8) -0.0007(9) O4 0.0665(12) 0.0933(14) 0.0665(12) -0.0160(11) 0.0152(10) 0.0029(11) C1 0.0431(13) 0.0730(17) 0.0497(14) -0.0019(13) -0.0041(11) -0.0005(12) C2 0.0493(14) 0.0769(18) 0.0436(14) -0.0039(13) -0.0015(11) -0.0072(12) C3 0.0659(17) 0.116(3) 0.0467(16) 0.0017(16) -0.0077(13) -0.0054(16) C4 0.082(2) 0.135(3) 0.0410(15) 0.0045(17) -0.0044(15) -0.0086(19) C5 0.076(2) 0.109(2) 0.0458(16) -0.0105(16) 0.0128(14) -0.0171(17) C6 0.0555(15) 0.085(2) 0.0519(16) -0.0088(14) 0.0097(13) -0.0050(13) C7 0.0482(14) 0.0668(17) 0.0413(13) -0.0045(12) 0.0020(11) -0.0062(11) C8 0.0382(12) 0.0539(15) 0.0460(13) -0.0008(11) 0.0062(10) -0.0025(10) C9 0.0349(11) 0.0573(15) 0.0474(14) -0.0010(11) -0.0006(10) 0.0003(10) C10 0.0306(11) 0.0605(15) 0.0515(14) -0.0015(11) 0.0007(10) 0.0008(10) C11 0.0339(11) 0.0536(14) 0.0472(13) 0.0001(11) 0.0009(10) -0.0007(10) C12 0.0363(12) 0.0538(15) 0.0457(13) 0.0043(11) -0.0006(10) -0.0001(10) C13 0.0345(11) 0.0469(13) 0.0493(13) 0.0016(11) 0.0009(10) -0.0015(9) C14 0.0354(12) 0.0475(13) 0.0558(14) 0.0094(12) 0.0070(10) 0.0024(10) C15 0.0373(12) 0.0561(15) 0.0671(16) 0.0066(13) -0.0013(11) 0.0005(11) C16 0.0399(13) 0.0656(17) 0.091(2) 0.0151(16) -0.0075(13) 0.0004(12) C17 0.0395(14) 0.0699(19) 0.102(2) 0.0269(17) 0.0062(16) 0.0055(13) C18 0.0593(16) 0.0655(18) 0.082(2) 0.0152(16) 0.0237(15) 0.0191(13) C19 0.0486(14) 0.0628(16) 0.0642(15) 0.0043(13) 0.0091(12) 0.0083(12) C20 0.0402(12) 0.0579(15) 0.0459(13) 0.0026(12) -0.0007(10) 0.0038(10) C21 0.0374(12) 0.0505(14) 0.0468(13) 0.0068(11) 0.0047(10) 0.0040(10) C22 0.0412(13) 0.0617(15) 0.0577(15) 0.0092(13) 0.0017(11) -0.0012(11) C23 0.0463(14) 0.0764(18) 0.0728(18) 0.0218(15) -0.0073(13) -0.0092(13) C24 0.0384(14) 0.083(2) 0.087(2) 0.0313(17) 0.0125(14) 0.0051(13) C25 0.0484(15) 0.0813(19) 0.0687(18) 0.0156(16) 0.0170(13) 0.0132(14) C26 0.0494(14) 0.0593(15) 0.0512(14) 0.0115(12) 0.0059(12) 0.0064(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 O1 C1 1.229(3) . ? O2 C8 1.362(2) . ? O2 C7 1.369(3) . ? O3 C20 1.239(3) . ? O4 C26 1.343(3) . ? O4 H4 0.8200 . ? C1 C2 1.463(3) . ? C1 C9 1.468(3) . ? C2 C7 1.388(3) . ? C2 C3 1.393(3) . ? C3 C4 1.362(4) . ? C3 H3 0.9300 . ? C4 C5 1.386(4) . ? C4 H4A 0.9300 . ? C5 C6 1.361(4) . ? C5 H5 0.9300 . ? C6 C7 1.386(3) . ? C6 H6 0.9300 . ? C8 C9 1.394(3) . ? C8 C13 1.400(3) . ? C9 C10 1.393(3) . ? C10 C11 1.373(3) . ? C10 H10 0.9300 . ? C11 C12 1.400(3) . ? C11 C20 1.485(3) . ? C12 C13 1.380(3) . ? C12 H12 0.9300 . ? C13 C14 1.493(3) . ? C14 C19 1.382(3) . ? C14 C15 1.383(3) . ? C15 C16 1.380(3) . ? C15 H15 0.9300 . ? C16 C17 1.354(4) . ? C16 H16 0.9300 . ? C17 C18 1.374(4) . ? C17 H17 0.9300 . ? C18 C19 1.397(3) . ? C18 H18 0.9300 . ? C19 H19 0.9300 . ? C20 C21 1.462(3) . ? C21 C22 1.393(3) . ? C21 C26 1.403(3) . ? C22 C23 1.370(3) . ? C22 H22 0.9300 . ? C23 C24 1.379(4) . ? C23 H23 0.9300 . ? C24 C25 1.363(4) . ? C24 H24 0.9300 . ? C25 C26 1.385(3) . ? C25 H25 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C8 O2 C7 120.09(17) . . ? C26 O4 H4 109.5 . . ? O1 C1 C2 122.9(2) . . ? O1 C1 C9 122.2(2) . . ? C2 C1 C9 114.8(2) . . ? C7 C2 C3 118.0(2) . . ? C7 C2 C1 119.9(2) . . ? C3 C2 C1 122.0(2) . . ? C4 C3 C2 120.7(3) . . ? C4 C3 H3 119.7 . . ? C2 C3 H3 119.7 . . ? C3 C4 C5 119.9(3) . . ? C3 C4 H4A 120.0 . . ? C5 C4 H4A 120.0 . . ? C6 C5 C4 121.3(2) . . ? C6 C5 H5 119.4 . . ? C4 C5 H5 119.4 . . ? C5 C6 C7 118.3(3) . . ? C5 C6 H6 120.8 . . ? C7 C6 H6 120.8 . . ? O2 C7 C6 115.6(2) . . ? O2 C7 C2 122.6(2) . . ? C6 C7 C2 121.7(2) . . ? O2 C8 C9 121.4(2) . . ? O2 C8 C13 116.25(18) . . ? C9 C8 C13 122.3(2) . . ? C10 C9 C8 118.9(2) . . ? C10 C9 C1 120.21(19) . . ? C8 C9 C1 120.9(2) . . ? C11 C10 C9 120.61(19) . . ? C11 C10 H10 119.7 . . ? C9 C10 H10 119.7 . . ? C10 C11 C12 118.76(19) . . ? C10 C11 C20 123.45(19) . . ? C12 C11 C20 117.38(19) . . ? C13 C12 C11 123.1(2) . . ? C13 C12 H12 118.4 . . ? C11 C12 H12 118.4 . . ? C12 C13 C8 116.25(19) . . ? C12 C13 C14 119.72(19) . . ? C8 C13 C14 123.99(18) . . ? C19 C14 C15 118.4(2) . . ? C19 C14 C13 122.7(2) . . ? C15 C14 C13 118.9(2) . . ? C16 C15 C14 121.1(2) . . ? C16 C15 H15 119.4 . . ? C14 C15 H15 119.4 . . ? C17 C16 C15 120.1(3) . . ? C17 C16 H16 120.0 . . ? C15 C16 H16 120.0 . . ? C16 C17 C18 120.5(2) . . ? C16 C17 H17 119.8 . . ? C18 C17 H17 119.8 . . ? C17 C18 C19 119.7(3) . . ? C17 C18 H18 120.1 . . ? C19 C18 H18 120.1 . . ? C14 C19 C18 120.2(3) . . ? C14 C19 H19 119.9 . . ? C18 C19 H19 119.9 . . ? O3 C20 C21 120.6(2) . . ? O3 C20 C11 117.48(19) . . ? C21 C20 C11 121.86(19) . . ? C22 C21 C26 118.3(2) . . ? C22 C21 C20 123.0(2) . . ? C26 C21 C20 118.6(2) . . ? C23 C22 C21 120.9(2) . . ? C23 C22 H22 119.5 . . ? C21 C22 H22 119.5 . . ? C22 C23 C24 119.4(3) . . ? C22 C23 H23 120.3 . . ? C24 C23 H23 120.3 . . ? C25 C24 C23 121.6(2) . . ? C25 C24 H24 119.2 . . ? C23 C24 H24 119.2 . . ? C24 C25 C26 119.4(3) . . ? C24 C25 H25 120.3 . . ? C26 C25 H25 120.3 . . ? O4 C26 C25 117.3(2) . . ? O4 C26 C21 122.4(2) . . ? C25 C26 C21 120.3(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 C7 -176.7(2) . . . . ? C9 C1 C2 C7 4.1(4) . . . . ? O1 C1 C2 C3 4.7(4) . . . . ? C9 C1 C2 C3 -174.5(2) . . . . ? C7 C2 C3 C4 0.3(4) . . . . ? C1 C2 C3 C4 178.9(3) . . . . ? C2 C3 C4 C5 1.0(5) . . . . ? C3 C4 C5 C6 -0.5(5) . . . . ? C4 C5 C6 C7 -1.3(4) . . . . ? C8 O2 C7 C6 176.5(2) . . . . ? C8 O2 C7 C2 -3.3(3) . . . . ? C5 C6 C7 O2 -177.1(2) . . . . ? C5 C6 C7 C2 2.7(4) . . . . ? C3 C2 C7 O2 177.5(2) . . . . ? C1 C2 C7 O2 -1.0(4) . . . . ? C3 C2 C7 C6 -2.2(4) . . . . ? C1 C2 C7 C6 179.2(2) . . . . ? C7 O2 C8 C9 4.2(3) . . . . ? C7 O2 C8 C13 -173.8(2) . . . . ? O2 C8 C9 C10 -179.7(2) . . . . ? C13 C8 C9 C10 -1.8(3) . . . . ? O2 C8 C9 C1 -0.9(3) . . . . ? C13 C8 C9 C1 177.0(2) . . . . ? O1 C1 C9 C10 -3.6(4) . . . . ? C2 C1 C9 C10 175.6(2) . . . . ? O1 C1 C9 C8 177.7(2) . . . . ? C2 C1 C9 C8 -3.1(3) . . . . ? C8 C9 C10 C11 0.7(3) . . . . ? C1 C9 C10 C11 -178.1(2) . . . . ? C9 C10 C11 C12 0.7(3) . . . . ? C9 C10 C11 C20 173.2(2) . . . . ? C10 C11 C12 C13 -1.2(3) . . . . ? C20 C11 C12 C13 -174.1(2) . . . . ? C11 C12 C13 C8 0.2(3) . . . . ? C11 C12 C13 C14 178.0(2) . . . . ? O2 C8 C13 C12 179.32(18) . . . . ? C9 C8 C13 C12 1.3(3) . . . . ? O2 C8 C13 C14 1.6(3) . . . . ? C9 C8 C13 C14 -176.4(2) . . . . ? C12 C13 C14 C19 141.0(2) . . . . ? C8 C13 C14 C19 -41.4(3) . . . . ? C12 C13 C14 C15 -36.9(3) . . . . ? C8 C13 C14 C15 140.7(2) . . . . ? C19 C14 C15 C16 -1.3(3) . . . . ? C13 C14 C15 C16 176.7(2) . . . . ? C14 C15 C16 C17 1.2(4) . . . . ? C15 C16 C17 C18 -0.6(4) . . . . ? C16 C17 C18 C19 0.3(4) . . . . ? C15 C14 C19 C18 0.9(3) . . . . ? C13 C14 C19 C18 -177.0(2) . . . . ? C17 C18 C19 C14 -0.4(4) . . . . ? C10 C11 C20 O3 -139.9(2) . . . . ? C12 C11 C20 O3 32.6(3) . . . . ? C10 C11 C20 C21 38.0(3) . . . . ? C12 C11 C20 C21 -149.5(2) . . . . ? O3 C20 C21 C22 -164.5(2) . . . . ? C11 C20 C21 C22 17.7(3) . . . . ? O3 C20 C21 C26 15.9(3) . . . . ? C11 C20 C21 C26 -161.9(2) . . . . ? C26 C21 C22 C23 1.6(3) . . . . ? C20 C21 C22 C23 -178.0(2) . . . . ? C21 C22 C23 C24 1.3(4) . . . . ? C22 C23 C24 C25 -2.6(4) . . . . ? C23 C24 C25 C26 0.9(4) . . . . ? C24 C25 C26 O4 -178.2(2) . . . . ? C24 C25 C26 C21 2.2(4) . . . . ? C22 C21 C26 O4 177.0(2) . . . . ? C20 C21 C26 O4 -3.4(3) . . . . ? C22 C21 C26 C25 -3.4(3) . . . . ? C20 C21 C26 C25 176.2(2) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O4 H4 O3 0.82 1.82 2.537(2) 144.9 . _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.233 _refine_diff_density_min -0.229 _refine_diff_density_rms 0.056