# Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2005 data_14cis _database_code_depnum_ccdc_archive 'CCDC 260556' _audit_creation_method SHELXL-97 _chemical_name_systematic (6aS*,11aS*)-6a,11a-dihydro-2,8-dimethoxy-6H-benzofuro[3,2-c]chromene _chemical_name_common cis-2,8-dihydroxypterocarpan _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C17 H16 O4' _chemical_formula_weight 284.30 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 triclinic _symmetry_space_group_name_H-M 'P 1' _symmetry_int_tables_number 1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' _cell_length_a 4.7090(7) _cell_length_b 8.2955(12) _cell_length_c 9.1628(13) _cell_angle_alpha 92.006(2) _cell_angle_beta 94.865(2) _cell_angle_gamma 104.989(3) _cell_volume 343.90(9) _cell_formula_units_Z 1 _cell_measurement_temperature 273(2) _cell_measurement_reflns_used 1220 _cell_measurement_theta_min 5.093 _cell_measurement_theta_max 46.474 _exptl_crystal_description prismatic _exptl_crystal_colour colorless _exptl_crystal_size_max 0.410 _exptl_crystal_size_mid 0.110 _exptl_crystal_size_min 0.055 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.373 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 150 _exptl_absorpt_coefficient_mu 0.098 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 273(2) _diffrn_radiation_probe ? _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_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 1581 _diffrn_reflns_av_R_equivalents 0.0195 _diffrn_reflns_av_sigmaI/netI 0.0267 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 5 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 2.23 _diffrn_reflns_theta_max 23.27 _reflns_number_total 1206 _reflns_number_gt 1132 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX' _computing_cell_refinement 'Bruker APEX' _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^)+(0.0415P)^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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.9(12) _refine_ls_number_reflns 1206 _refine_ls_number_parameters 192 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0321 _refine_ls_R_factor_gt 0.0300 _refine_ls_wR_factor_ref 0.0697 _refine_ls_wR_factor_gt 0.0686 _refine_ls_goodness_of_fit_ref 1.007 _refine_ls_restrained_S_all 1.006 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.2457(5) 0.9774(3) 1.0244(2) 0.0736(7) Uani 1 1 d . . . C21 C 0.6010(6) 0.9258(3) 0.3825(3) 0.0484(7) Uani 1 1 d . . . H21A H 0.7966 0.9922 0.4201 0.058 Uiso 1 1 calc R . . H21B H 0.5881 0.9254 0.2763 0.058 Uiso 1 1 calc R . . O3 O 0.3283(4) 0.5744(2) 0.61066(19) 0.0555(5) Uani 1 1 d . . . O4 O -0.2764(5) 0.4268(3) 0.0635(2) 0.0779(7) Uani 1 1 d . . . C1 C 0.2817(6) 0.9921(4) 0.8779(3) 0.0515(7) Uani 1 1 d . . . C2 C 0.2136(6) 1.1158(4) 0.7954(3) 0.0572(8) Uani 1 1 d . . . H2 H 0.1373 1.1968 0.8382 0.069 Uiso 1 1 calc R . . C3 C 0.2602(6) 1.1176(3) 0.6486(3) 0.0509(7) Uani 1 1 d . . . H3 H 0.2193 1.2021 0.5933 0.061 Uiso 1 1 calc R . . C4 C 0.3661(5) 0.9967(3) 0.5832(3) 0.0411(7) Uani 1 1 d . . . C5 C 0.4369(5) 0.8719(3) 0.6635(3) 0.0423(7) Uani 1 1 d . . . C6 C 0.3953(5) 0.8733(4) 0.8119(3) 0.0497(7) Uani 1 1 d . . . H6 H 0.4453 0.7919 0.8684 0.060 Uiso 1 1 calc R . . C7 C 0.2783(5) 0.6267(3) 0.3665(3) 0.0438(7) Uani 1 1 d . . . C8 C 0.1407(6) 0.5974(3) 0.2246(3) 0.0508(7) Uani 1 1 d . . . H8 H 0.2191 0.6613 0.1490 0.061 Uiso 1 1 calc R . . C9 C -0.1187(6) 0.4693(4) 0.1989(3) 0.0536(8) Uani 1 1 d . . . C10 C -0.2353(6) 0.3759(4) 0.3124(3) 0.0583(8) Uani 1 1 d . . . H10 H -0.4094 0.2913 0.2935 0.070 Uiso 1 1 calc R . . C11 C -0.0972(6) 0.4065(3) 0.4527(3) 0.0532(8) Uani 1 1 d . . . H11 H -0.1756 0.3439 0.5290 0.064 Uiso 1 1 calc R . . C12 C 0.1598(6) 0.5322(3) 0.4770(3) 0.0456(7) Uani 1 1 d . . . C20 C 0.0959(7) 1.0841(5) 1.0904(3) 0.0782(10) Uani 1 1 d . . . H20A H 0.2018 1.1984 1.0821 0.117 Uiso 1 1 calc R . . H20B H 0.0841 1.0619 1.1921 0.117 Uiso 1 1 calc R . . H20C H -0.0997 1.0642 1.0417 0.117 Uiso 1 1 calc R . . O2 O 0.3859(4) 1.0024(2) 0.43407(17) 0.0501(5) Uani 1 1 d . . . C22 C 0.5617(5) 0.7495(3) 0.4281(3) 0.0476(7) Uani 1 1 d . . . H22 H 0.7286 0.7091 0.4000 0.057 Uiso 1 1 calc R . . C23 C -0.1612(9) 0.5114(5) -0.0583(4) 0.0893(11) Uani 1 1 d . . . H23A H -0.1349 0.6294 -0.0406 0.134 Uiso 1 1 calc R . . H23B H -0.2961 0.4723 -0.1444 0.134 Uiso 1 1 calc R . . H23C H 0.0257 0.4902 -0.0727 0.134 Uiso 1 1 calc R . . C24 C 0.5429(6) 0.7347(3) 0.5943(3) 0.0462(6) Uani 1 1 d . . . H24 H 0.7363 0.7340 0.6426 0.055 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 0.0920(16) 0.0883(17) 0.0467(12) 0.0122(12) 0.0193(11) 0.0294(13) C21 0.0399(15) 0.0506(17) 0.0527(16) 0.0064(14) 0.0073(13) 0.0071(13) O3 0.0625(12) 0.0448(12) 0.0590(12) 0.0120(10) 0.0010(9) 0.0139(10) O4 0.0778(15) 0.0710(16) 0.0660(14) 0.0027(12) -0.0059(12) -0.0101(13) C1 0.0483(16) 0.0580(19) 0.0456(16) 0.0033(15) 0.0039(12) 0.0094(15) C2 0.0611(18) 0.0527(19) 0.0589(19) -0.0036(16) 0.0077(15) 0.0171(15) C3 0.0554(17) 0.0433(17) 0.0551(17) 0.0085(14) 0.0009(13) 0.0157(14) C4 0.0387(14) 0.0400(16) 0.0417(15) 0.0058(13) 0.0053(12) 0.0042(13) C5 0.0353(14) 0.0440(16) 0.0461(15) 0.0081(13) 0.0012(12) 0.0080(12) C6 0.0479(16) 0.0504(18) 0.0502(17) 0.0145(14) 0.0032(13) 0.0109(14) C7 0.0409(15) 0.0379(17) 0.0570(17) 0.0055(13) 0.0093(13) 0.0163(12) C8 0.0535(17) 0.0453(17) 0.0553(18) 0.0065(14) 0.0106(14) 0.0139(15) C9 0.0560(18) 0.0404(17) 0.0601(18) -0.0008(16) -0.0017(15) 0.0078(14) C10 0.0544(18) 0.0402(17) 0.076(2) 0.0038(16) 0.0042(16) 0.0045(14) C11 0.0552(17) 0.0368(17) 0.069(2) 0.0141(15) 0.0118(15) 0.0107(14) C12 0.0474(16) 0.0357(16) 0.0560(17) 0.0093(14) 0.0053(14) 0.0139(13) C20 0.0628(19) 0.116(3) 0.0534(17) -0.0082(19) 0.0110(15) 0.020(2) O2 0.0566(11) 0.0499(11) 0.0467(11) 0.0095(9) 0.0054(8) 0.0183(9) C22 0.0345(13) 0.0497(17) 0.0597(16) 0.0031(13) 0.0066(12) 0.0125(12) C23 0.104(3) 0.087(3) 0.063(2) 0.0090(19) -0.0071(19) 0.004(2) C24 0.0414(14) 0.0410(15) 0.0573(16) 0.0072(13) 0.0029(12) 0.0129(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 1.373(3) . ? O1 C20 1.416(4) . ? C21 O2 1.430(3) . ? C21 C22 1.505(4) . ? C21 H21A 0.9700 . ? C21 H21B 0.9700 . ? O3 C12 1.383(3) . ? O3 C24 1.469(3) . ? O4 C9 1.375(3) . ? O4 C23 1.412(4) . ? C1 C6 1.381(4) . ? C1 C2 1.382(4) . ? C2 C3 1.381(4) . ? C2 H2 0.9300 . ? C3 C4 1.371(3) . ? C3 H3 0.9300 . ? C4 O2 1.379(3) . ? C4 C5 1.383(3) . ? C5 C6 1.391(3) . ? C5 C24 1.498(4) . ? C6 H6 0.9300 . ? C7 C12 1.370(3) . ? C7 C8 1.387(3) . ? C7 C22 1.505(3) . ? C8 C9 1.393(4) . ? C8 H8 0.9300 . ? C9 C10 1.385(4) . ? C10 C11 1.375(3) . ? C10 H10 0.9300 . ? C11 C12 1.373(3) . ? C11 H11 0.9300 . ? C20 H20A 0.9600 . ? C20 H20B 0.9600 . ? C20 H20C 0.9600 . ? C22 C24 1.540(4) . ? C22 H22 0.9800 . ? C23 H23A 0.9600 . ? C23 H23B 0.9600 . ? C23 H23C 0.9600 . ? C24 H24 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 O1 C20 117.2(3) . . ? O2 C21 C22 113.0(2) . . ? O2 C21 H21A 109.0 . . ? C22 C21 H21A 109.0 . . ? O2 C21 H21B 109.0 . . ? C22 C21 H21B 109.0 . . ? H21A C21 H21B 107.8 . . ? C12 O3 C24 106.26(19) . . ? C9 O4 C23 118.3(2) . . ? O1 C1 C6 116.1(3) . . ? O1 C1 C2 124.6(3) . . ? C6 C1 C2 119.4(2) . . ? C3 C2 C1 119.2(3) . . ? C3 C2 H2 120.4 . . ? C1 C2 H2 120.4 . . ? C4 C3 C2 121.1(3) . . ? C4 C3 H3 119.5 . . ? C2 C3 H3 119.5 . . ? C3 C4 O2 116.8(2) . . ? C3 C4 C5 120.8(2) . . ? O2 C4 C5 122.3(2) . . ? C4 C5 C6 117.7(3) . . ? C4 C5 C24 122.2(2) . . ? C6 C5 C24 120.1(2) . . ? C1 C6 C5 121.9(3) . . ? C1 C6 H6 119.1 . . ? C5 C6 H6 119.1 . . ? C12 C7 C8 120.5(2) . . ? C12 C7 C22 108.8(2) . . ? C8 C7 C22 130.7(2) . . ? C7 C8 C9 117.9(3) . . ? C7 C8 H8 121.0 . . ? C9 C8 H8 121.0 . . ? O4 C9 C10 115.6(2) . . ? O4 C9 C8 123.8(3) . . ? C10 C9 C8 120.6(3) . . ? C11 C10 C9 120.9(3) . . ? C11 C10 H10 119.5 . . ? C9 C10 H10 119.5 . . ? C12 C11 C10 118.1(3) . . ? C12 C11 H11 120.9 . . ? C10 C11 H11 120.9 . . ? C7 C12 C11 122.0(3) . . ? C7 C12 O3 113.1(2) . . ? C11 C12 O3 124.9(2) . . ? O1 C20 H20A 109.5 . . ? O1 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? O1 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C4 O2 C21 114.1(2) . . ? C21 C22 C7 115.4(2) . . ? C21 C22 C24 112.8(2) . . ? C7 C22 C24 101.5(2) . . ? C21 C22 H22 108.9 . . ? C7 C22 H22 108.9 . . ? C24 C22 H22 108.9 . . ? 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 . . ? O3 C24 C5 108.7(2) . . ? O3 C24 C22 105.96(19) . . ? C5 C24 C22 112.7(2) . . ? O3 C24 H24 109.8 . . ? C5 C24 H24 109.8 . . ? C22 C24 H24 109.8 . . ? 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 C20 O1 C1 C6 -172.3(2) . . . . ? C20 O1 C1 C2 8.0(4) . . . . ? O1 C1 C2 C3 179.9(2) . . . . ? C6 C1 C2 C3 0.1(4) . . . . ? C1 C2 C3 C4 1.6(4) . . . . ? C2 C3 C4 O2 175.6(2) . . . . ? C2 C3 C4 C5 -1.8(4) . . . . ? C3 C4 C5 C6 0.4(3) . . . . ? O2 C4 C5 C6 -176.9(2) . . . . ? C3 C4 C5 C24 177.8(2) . . . . ? O2 C4 C5 C24 0.5(3) . . . . ? O1 C1 C6 C5 178.7(2) . . . . ? C2 C1 C6 C5 -1.5(4) . . . . ? C4 C5 C6 C1 1.3(4) . . . . ? C24 C5 C6 C1 -176.2(2) . . . . ? C12 C7 C8 C9 -0.3(4) . . . . ? C22 C7 C8 C9 177.6(3) . . . . ? C23 O4 C9 C10 -176.8(3) . . . . ? C23 O4 C9 C8 3.7(5) . . . . ? C7 C8 C9 O4 -179.8(3) . . . . ? C7 C8 C9 C10 0.6(4) . . . . ? O4 C9 C10 C11 179.9(3) . . . . ? C8 C9 C10 C11 -0.5(4) . . . . ? C9 C10 C11 C12 -0.1(4) . . . . ? C8 C7 C12 C11 -0.2(4) . . . . ? C22 C7 C12 C11 -178.5(2) . . . . ? C8 C7 C12 O3 178.3(2) . . . . ? C22 C7 C12 O3 0.0(3) . . . . ? C10 C11 C12 C7 0.4(4) . . . . ? C10 C11 C12 O3 -177.9(3) . . . . ? C24 O3 C12 C7 13.2(3) . . . . ? C24 O3 C12 C11 -168.3(2) . . . . ? C3 C4 O2 C21 155.1(2) . . . . ? C5 C4 O2 C21 -27.5(3) . . . . ? C22 C21 O2 C4 53.2(3) . . . . ? O2 C21 C22 C7 64.0(3) . . . . ? O2 C21 C22 C24 -52.1(3) . . . . ? C12 C7 C22 C21 -134.6(2) . . . . ? C8 C7 C22 C21 47.3(4) . . . . ? C12 C7 C22 C24 -12.3(3) . . . . ? C8 C7 C22 C24 169.6(3) . . . . ? C12 O3 C24 C5 100.9(2) . . . . ? C12 O3 C24 C22 -20.5(3) . . . . ? C4 C5 C24 O3 -117.3(2) . . . . ? C6 C5 C24 O3 60.1(3) . . . . ? C4 C5 C24 C22 -0.1(3) . . . . ? C6 C5 C24 C22 177.3(2) . . . . ? C21 C22 C24 O3 143.7(2) . . . . ? C7 C22 C24 O3 19.6(3) . . . . ? C21 C22 C24 C5 25.0(3) . . . . ? C7 C22 C24 C5 -99.1(2) . . . . ? _diffrn_measured_fraction_theta_max 0.987 _diffrn_reflns_theta_full 23.27 _diffrn_measured_fraction_theta_full 0.987 _refine_diff_density_max 0.090 _refine_diff_density_min -0.109 _refine_diff_density_rms 0.025 data_14trans _database_code_depnum_ccdc_archive 'CCDC 260557' _audit_creation_method SHELXL-97 _chemical_name_systematic (6aR*,11aS*)-6a,11a-dihydro-2,8-dimethoxy-6H-benzofuro[3,2-c]chromene _chemical_name_common trans-2,8-dimethoxypterocarpan _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C17 H16 O4' _chemical_formula_weight 284.30 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 triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_int_tables_number 2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.0941(8) _cell_length_b 8.7487(8) _cell_length_c 10.2094(10) _cell_angle_alpha 78.617(2) _cell_angle_beta 82.940(2) _cell_angle_gamma 77.161(2) _cell_volume 688.65(11) _cell_formula_units_Z 2 _cell_measurement_temperature 273(2) _cell_measurement_reflns_used 1243 _cell_measurement_theta_min 5.093 _cell_measurement_theta_max 47.619 _exptl_crystal_description prismatic _exptl_crystal_colour colorless _exptl_crystal_size_max 0.270 _exptl_crystal_size_mid 0.150 _exptl_crystal_size_min 0.080 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.371 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 300 _exptl_absorpt_coefficient_mu 0.097 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 273(2) _diffrn_radiation_probe ? _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_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 3775 _diffrn_reflns_av_R_equivalents 0.0247 _diffrn_reflns_av_sigmaI/netI 0.0419 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.04 _diffrn_reflns_theta_max 25.02 _reflns_number_total 2407 _reflns_number_gt 1723 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX' _computing_cell_refinement 'Bruker APEX' _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^)+(0.1122P)^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 2407 _refine_ls_number_parameters 192 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0810 _refine_ls_R_factor_gt 0.0579 _refine_ls_wR_factor_ref 0.1901 _refine_ls_wR_factor_gt 0.1687 _refine_ls_goodness_of_fit_ref 1.070 _refine_ls_restrained_S_all 1.070 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 1.5020(2) 0.5856(2) 0.67331(18) 0.0604(6) Uani 1 1 d . . . O2 O 0.8222(2) 0.8737(2) 0.65100(18) 0.0603(6) Uani 1 1 d . . . O3 O 1.0555(2) 0.6553(2) 0.32803(17) 0.0492(5) Uani 1 1 d . . . O4 O 0.4801(2) 0.7993(2) 0.05525(19) 0.0662(6) Uani 1 1 d . . . C1 C 1.0874(3) 0.7315(3) 0.5468(2) 0.0452(6) Uani 1 1 d . . . C2 C 1.2561(3) 0.6610(3) 0.5586(2) 0.0460(6) Uani 1 1 d . . . H2 H 1.3192 0.6149 0.4887 0.055 Uiso 1 1 calc R . . C3 C 1.3327(3) 0.6578(3) 0.6729(2) 0.0465(6) Uani 1 1 d . . . C4 C 1.2397(4) 0.7286(3) 0.7758(3) 0.0545(7) Uani 1 1 d . . . H4 H 1.2915 0.7295 0.8520 0.065 Uiso 1 1 calc R . . C5 C 1.0699(3) 0.7980(3) 0.7656(3) 0.0520(7) Uani 1 1 d . . . H5 H 1.0072 0.8436 0.8359 0.062 Uiso 1 1 calc R . . C6 C 0.9930(3) 0.8003(3) 0.6529(3) 0.0460(6) Uani 1 1 d . . . C7 C 0.7673(3) 0.7569(3) 0.3176(3) 0.0509(7) Uani 1 1 d . . . C8 C 0.9167(3) 0.6855(3) 0.2526(2) 0.0446(6) Uani 1 1 d . . . C9 C 0.9195(3) 0.6503(3) 0.1274(3) 0.0539(7) Uani 1 1 d . . . H9 H 1.0195 0.6005 0.0850 0.065 Uiso 1 1 calc R . . C10 C 0.7691(3) 0.6911(3) 0.0662(3) 0.0561(7) Uani 1 1 d . . . H10 H 0.7686 0.6688 -0.0191 0.067 Uiso 1 1 calc R . . C11 C 0.6195(3) 0.7641(3) 0.1282(3) 0.0527(7) Uani 1 1 d . . . C12 C 0.6164(3) 0.7952(3) 0.2566(3) 0.0578(8) Uani 1 1 d . . . H12 H 0.5153 0.8407 0.3007 0.069 Uiso 1 1 calc R . . C20 C 1.5851(4) 0.5836(4) 0.7893(3) 0.0673(9) Uani 1 1 d . . . H20A H 1.5737 0.6907 0.8040 0.101 Uiso 1 1 calc R . . H20B H 1.7035 0.5363 0.7760 0.101 Uiso 1 1 calc R . . H20C H 1.5341 0.5226 0.8659 0.101 Uiso 1 1 calc R . . C21 C 0.7319(3) 0.8882(3) 0.5339(3) 0.0549(7) Uani 1 1 d . . . H21A H 0.7305 0.9925 0.4791 0.066 Uiso 1 1 calc R . . H21B H 0.6152 0.8786 0.5618 0.066 Uiso 1 1 calc R . . C22 C 0.8133(3) 0.7641(4) 0.4540(3) 0.0616(8) Uani 1 1 d . . . H22 H 0.8020 0.6619 0.5106 0.074 Uiso 1 1 calc R . . C23 C 0.9958(4) 0.7586(4) 0.4244(3) 0.0627(8) Uani 1 1 d . . . H23 H 1.0060 0.8654 0.3771 0.075 Uiso 1 1 calc R . . C24 C 0.3245(4) 0.8832(4) 0.1119(3) 0.0706(9) Uani 1 1 d . . . H24A H 0.2885 0.8195 0.1937 0.106 Uiso 1 1 calc R . . H24B H 0.2389 0.9047 0.0497 0.106 Uiso 1 1 calc R . . H24C H 0.3415 0.9818 0.1303 0.106 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 0.0439(11) 0.0871(14) 0.0532(12) -0.0311(10) -0.0116(9) 0.0010(9) O2 0.0480(11) 0.0797(13) 0.0554(12) -0.0353(10) -0.0068(9) 0.0045(9) O3 0.0417(10) 0.0616(11) 0.0458(10) -0.0232(8) -0.0059(8) -0.0005(8) O4 0.0465(11) 0.0941(15) 0.0607(13) -0.0332(11) -0.0151(9) 0.0033(10) C1 0.0457(14) 0.0486(15) 0.0437(14) -0.0164(11) -0.0046(11) -0.0070(12) C2 0.0458(15) 0.0526(15) 0.0444(15) -0.0210(12) -0.0008(12) -0.0105(12) C3 0.0443(14) 0.0527(15) 0.0450(15) -0.0137(12) -0.0064(12) -0.0092(12) C4 0.0591(17) 0.0673(18) 0.0408(15) -0.0200(13) -0.0083(13) -0.0091(14) C5 0.0542(16) 0.0608(17) 0.0403(15) -0.0185(12) 0.0001(12) -0.0040(13) C6 0.0450(14) 0.0470(14) 0.0469(15) -0.0144(11) -0.0035(12) -0.0056(11) C7 0.0456(15) 0.0633(17) 0.0452(15) -0.0206(12) -0.0058(12) -0.0031(12) C8 0.0393(13) 0.0519(15) 0.0436(14) -0.0141(11) -0.0046(11) -0.0053(11) C9 0.0450(15) 0.0694(18) 0.0483(16) -0.0261(13) -0.0017(12) -0.0011(13) C10 0.0536(17) 0.0720(18) 0.0454(15) -0.0257(13) -0.0060(13) -0.0041(14) C11 0.0455(15) 0.0640(17) 0.0497(16) -0.0184(13) -0.0107(13) -0.0027(13) C12 0.0428(15) 0.0772(19) 0.0544(17) -0.0283(14) -0.0021(13) -0.0006(13) C20 0.0532(17) 0.094(2) 0.0576(18) -0.0258(16) -0.0187(14) -0.0016(16) C21 0.0478(16) 0.0665(18) 0.0521(16) -0.0240(13) -0.0082(13) -0.0007(13) C22 0.0510(16) 0.083(2) 0.0522(17) -0.0272(14) -0.0057(13) -0.0023(14) C23 0.0512(17) 0.084(2) 0.0561(17) -0.0378(15) -0.0079(14) 0.0040(14) C24 0.0436(16) 0.098(2) 0.068(2) -0.0255(17) -0.0117(14) 0.0033(15) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C3 1.376(3) . ? O1 C20 1.427(3) . ? O2 C6 1.390(3) . ? O2 C21 1.447(3) . ? O3 C8 1.388(3) . ? O3 C23 1.435(3) . ? O4 C11 1.373(3) . ? O4 C24 1.427(3) . ? C1 C2 1.378(3) . ? C1 C6 1.402(4) . ? C1 C23 1.483(4) . ? C2 C3 1.380(3) . ? C2 H2 0.9300 . ? C3 C4 1.382(4) . ? C4 C5 1.381(4) . ? C4 H4 0.9300 . ? C5 C6 1.369(4) . ? C5 H5 0.9300 . ? C7 C12 1.384(4) . ? C7 C8 1.387(4) . ? C7 C22 1.501(4) . ? C8 C9 1.369(4) . ? C9 C10 1.381(4) . ? C9 H9 0.9300 . ? C10 C11 1.379(4) . ? C10 H10 0.9300 . ? C11 C12 1.386(4) . ? C12 H12 0.9300 . ? C20 H20A 0.9600 . ? C20 H20B 0.9600 . ? C20 H20C 0.9600 . ? C21 C22 1.476(4) . ? C21 H21A 0.9700 . ? C21 H21B 0.9700 . ? C22 C23 1.463(4) . ? C22 H22 0.9800 . ? C23 H23 0.9800 . ? C24 H24A 0.9600 . ? C24 H24B 0.9600 . ? C24 H24C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C3 O1 C20 117.0(2) . . ? C6 O2 C21 120.62(19) . . ? C8 O3 C23 101.75(19) . . ? C11 O4 C24 117.6(2) . . ? C2 C1 C6 119.3(2) . . ? C2 C1 C23 125.9(2) . . ? C6 C1 C23 114.5(2) . . ? C1 C2 C3 120.8(2) . . ? C1 C2 H2 119.6 . . ? C3 C2 H2 119.6 . . ? O1 C3 C2 115.9(2) . . ? O1 C3 C4 124.5(2) . . ? C2 C3 C4 119.6(2) . . ? C5 C4 C3 120.1(2) . . ? C5 C4 H4 120.0 . . ? C3 C4 H4 120.0 . . ? C6 C5 C4 120.5(2) . . ? C6 C5 H5 119.7 . . ? C4 C5 H5 119.7 . . ? C5 C6 O2 116.6(2) . . ? C5 C6 C1 119.8(2) . . ? O2 C6 C1 123.7(2) . . ? C12 C7 C8 120.5(3) . . ? C12 C7 C22 134.0(3) . . ? C8 C7 C22 105.4(2) . . ? C9 C8 C7 121.3(2) . . ? C9 C8 O3 125.8(2) . . ? C7 C8 O3 112.9(2) . . ? C8 C9 C10 117.9(3) . . ? C8 C9 H9 121.1 . . ? C10 C9 H9 121.1 . . ? C11 C10 C9 121.7(3) . . ? C11 C10 H10 119.1 . . ? C9 C10 H10 119.1 . . ? O4 C11 C10 115.5(2) . . ? O4 C11 C12 124.4(3) . . ? C10 C11 C12 120.1(3) . . ? C7 C12 C11 118.4(3) . . ? C7 C12 H12 120.8 . . ? C11 C12 H12 120.8 . . ? O1 C20 H20A 109.5 . . ? O1 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? O1 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? O2 C21 C22 111.0(2) . . ? O2 C21 H21A 109.4 . . ? C22 C21 H21A 109.4 . . ? O2 C21 H21B 109.4 . . ? C22 C21 H21B 109.4 . . ? H21A C21 H21B 108.0 . . ? C23 C22 C21 112.0(3) . . ? C23 C22 C7 99.6(2) . . ? C21 C22 C7 125.1(2) . . ? C23 C22 H22 106.3 . . ? C21 C22 H22 106.3 . . ? C7 C22 H22 106.3 . . ? O3 C23 C22 107.2(2) . . ? O3 C23 C1 118.8(2) . . ? C22 C23 C1 112.9(2) . . ? O3 C23 H23 105.7 . . ? C22 C23 H23 105.7 . . ? C1 C23 H23 105.7 . . ? O4 C24 H24A 109.5 . . ? O4 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? O4 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C1 C2 C3 -0.2(4) . . . . ? C23 C1 C2 C3 172.8(2) . . . . ? C20 O1 C3 C2 178.8(2) . . . . ? C20 O1 C3 C4 0.5(4) . . . . ? C1 C2 C3 O1 -179.4(2) . . . . ? C1 C2 C3 C4 -1.1(4) . . . . ? O1 C3 C4 C5 180.0(2) . . . . ? C2 C3 C4 C5 1.9(4) . . . . ? C3 C4 C5 C6 -1.3(4) . . . . ? C4 C5 C6 O2 -179.5(2) . . . . ? C4 C5 C6 C1 0.0(4) . . . . ? C21 O2 C6 C5 177.3(2) . . . . ? C21 O2 C6 C1 -2.2(4) . . . . ? C2 C1 C6 C5 0.7(4) . . . . ? C23 C1 C6 C5 -173.0(2) . . . . ? C2 C1 C6 O2 -179.8(2) . . . . ? C23 C1 C6 O2 6.5(4) . . . . ? C12 C7 C8 C9 -0.3(4) . . . . ? C22 C7 C8 C9 175.8(2) . . . . ? C12 C7 C8 O3 -179.9(2) . . . . ? C22 C7 C8 O3 -3.9(3) . . . . ? C23 O3 C8 C9 162.1(3) . . . . ? C23 O3 C8 C7 -18.3(3) . . . . ? C7 C8 C9 C10 1.3(4) . . . . ? O3 C8 C9 C10 -179.1(2) . . . . ? C8 C9 C10 C11 -0.4(4) . . . . ? C24 O4 C11 C10 -176.4(2) . . . . ? C24 O4 C11 C12 4.5(4) . . . . ? C9 C10 C11 O4 179.4(2) . . . . ? C9 C10 C11 C12 -1.5(4) . . . . ? C8 C7 C12 C11 -1.6(4) . . . . ? C22 C7 C12 C11 -176.3(3) . . . . ? O4 C11 C12 C7 -178.5(2) . . . . ? C10 C11 C12 C7 2.5(4) . . . . ? C6 O2 C21 C22 24.4(3) . . . . ? O2 C21 C22 C23 -51.3(3) . . . . ? O2 C21 C22 C7 -171.5(2) . . . . ? C12 C7 C22 C23 -161.0(3) . . . . ? C8 C7 C22 C23 23.7(3) . . . . ? C12 C7 C22 C21 -35.4(5) . . . . ? C8 C7 C22 C21 149.3(3) . . . . ? C8 O3 C23 C22 34.2(3) . . . . ? C8 O3 C23 C1 163.6(2) . . . . ? C21 C22 C23 O3 -170.0(2) . . . . ? C7 C22 C23 O3 -35.9(3) . . . . ? C21 C22 C23 C1 57.3(4) . . . . ? C7 C22 C23 C1 -168.6(2) . . . . ? C2 C1 C23 O3 26.4(4) . . . . ? C6 C1 C23 O3 -160.4(2) . . . . ? C2 C1 C23 C22 153.1(3) . . . . ? C6 C1 C23 C22 -33.7(4) . . . . ? _diffrn_measured_fraction_theta_max 0.986 _diffrn_reflns_theta_full 25.02 _diffrn_measured_fraction_theta_full 0.986 _refine_diff_density_max 0.364 _refine_diff_density_min -0.348 _refine_diff_density_rms 0.087