Supplementary Material (ESI) for Chemical Communications This journal is © The Royal Society of Chemistry 2001 ---------- X-Sun-Charset: us-ascii X-Sun-Content-Lines: 344 data_global _journal_coden_Cambridge 182 loop_ _publ_author_name 'Che, Chi-ming' 'Lai, W-Y' 'Lee, S-T' 'Lin, Wei-Zhu' 'Wan, Chun-Wai' 'Yu, Wing-Yiu' 'Zhou, Zhong-Yuan' _publ_contact_author ; Dr Chi-ming Che Department of Chemistry University of Hong Kong Pokfulam Road HONG KONG ; data_w15 _database_code_CSD 156695 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C32 H32 N2 O8' _chemical_formula_weight 572.60 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Ibam loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z' '-x+1/2, y+1/2, -z' 'x+1/2, -y+1/2, -z' 'x+1/2, y+1/2, z+1/2' '-x+1/2, -y+1/2, z+1/2' '-x+1, y+1, -z+1/2' 'x+1, -y+1, -z+1/2' '-x, -y, -z' 'x, y, -z' 'x-1/2, -y-1/2, z' '-x-1/2, y-1/2, z' '-x+1/2, -y+1/2, -z+1/2' 'x+1/2, y+1/2, -z+1/2' 'x, -y, z+1/2' '-x, y, z+1/2' _cell_length_a 14.3634(19) _cell_length_b 27.535(4) _cell_length_c 7.2722(10) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2876.2(7) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used CCD _cell_measurement_theta_min 1 _cell_measurement_theta_max 27.5 _exptl_crystal_description NEEDLE _exptl_crystal_colour COLORLESS _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.322 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1208 _exptl_absorpt_coefficient_mu 0.096 _exptl_absorpt_correction_type SADABS _exptl_absorpt_correction_T_min 0.637 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type BRUKER CCD AREA DETECTOR DDIFRACTOMETER _diffrn_measurement_method PHI and OMEGA SCAN _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9113 _diffrn_reflns_av_R_equivalents 0.0561 _diffrn_reflns_av_sigmaI/netI 0.0354 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -34 _diffrn_reflns_limit_k_max 35 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 2.63 _diffrn_reflns_theta_max 27.56 _reflns_number_total 1742 _reflns_number_gt 1001 _reflns_threshold_expression >2sigma(I) _computing_data_collection BRUKER SMART _computing_cell_refinement BRUKER SMART _computing_data_reduction SHELXTL _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics SHELXTL _computing_publication_material 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^)+(0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0013(2) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 1742 _refine_ls_number_parameters 131 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0901 _refine_ls_R_factor_gt 0.0536 _refine_ls_wR_factor_ref 0.1674 _refine_ls_wR_factor_gt 0.1484 _refine_ls_goodness_of_fit_ref 0.963 _refine_ls_restrained_S_all 0.963 _refine_ls_shift/su_max 0.007 _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 -0.09185(5) 0.39891(3) 0.5000 0.0600(3) Uani 1 2 d S . . O2 O 0.03205(5) 0.35191(3) 0.5000 0.0627(3) Uani 1 2 d S . . O3 O 0.35806(5) 0.45883(3) 0.5000 0.0861(4) Uani 1 2 d S . . O4 O 0.30841(5) 0.53528(3) 0.5000 0.0735(3) Uani 1 2 d S . . N1 N 0.12671(5) 0.50743(3) 0.5000 0.0416(2) Uani 1 2 d S . . H1A H 0.1356 0.5403 0.5000 0.050 Uiso 1 2 d S . . C1 C 0.06012(7) 0.43471(3) 0.5000 0.0382(3) Uani 1 2 d S . . C2 C 0.15816(7) 0.42830(3) 0.5000 0.0411(3) Uani 1 2 d S . . C3 C 0.19712(7) 0.47384(4) 0.5000 0.0438(3) Uani 1 2 d S . . C4 C 0.04255(6) 0.48544(3) 0.5000 0.0353(3) Uani 1 2 d S . . C5 C -0.00772(7) 0.39537(3) 0.5000 0.0405(3) Uani 1 2 d S . . C6 C -0.02833(8) 0.30974(4) 0.5000 0.0619(4) Uani 1 2 d S . . H6A H -0.0680 0.3098 0.3926 0.074 Uiso 0.50 1 d P . . C7 C 0.03639(10) 0.26635(5) 0.5000 0.0749(5) Uani 1 2 d S . . H7A H 0.0037(13) 0.2386(6) 0.5000 0.112 Uiso 1 2 d S . . H7B H 0.0811(19) 0.2655(8) 0.382(3) 0.112 Uiso 0.50 1 d P . . C8 C 0.21126(7) 0.38190(4) 0.5000 0.0455(3) Uani 1 2 d S . . C9 C 0.23473(6) 0.35961(3) 0.33665(15) 0.0624(3) Uani 1 1 d . . . H9A H 0.2207 0.3747 0.2256 0.075 Uiso 1 1 calc R . . C10 C 0.27903(7) 0.31499(3) 0.33662(19) 0.0812(3) Uani 1 1 d . . . H10A H 0.2943 0.3001 0.2259 0.097 Uiso 1 1 calc R . . C11 C 0.30038(10) 0.29271(5) 0.5000 0.0891(6) Uani 1 2 d S . . H11A H 0.3293 0.2625 0.5000 0.107 Uiso 1 2 calc SR . . C12 C 0.29631(7) 0.48747(4) 0.5000 0.0548(4) Uani 1 2 d S . . C13 C 0.40708(10) 0.55061(6) 0.5000 0.1095(8) Uani 1 2 d S . . H13A H 0.4382 0.5377 0.3933 0.131 Uiso 0.50 1 d P . . C14 C 0.41635(13) 0.59982(7) 0.5000 0.1603(14) Uani 1 2 d S . . H14A H 0.471(3) 0.6107(12) 0.5000 0.240 Uiso 1 2 d S . . H14B H 0.396(3) 0.6213(15) 0.5000 0.240 Uiso 1 2 d S . . 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 0.0333(4) 0.0380(4) 0.1088(6) 0.000 0.000 0.0022(3) O2 0.0370(4) 0.0314(4) 0.1197(7) 0.000 0.000 0.0026(3) O3 0.0319(4) 0.0537(5) 0.1728(10) 0.000 0.000 0.0086(4) O4 0.0320(4) 0.0436(4) 0.1449(8) 0.000 0.000 -0.0016(3) N1 0.0287(4) 0.0324(4) 0.0637(5) 0.000 0.000 0.0021(3) C1 0.0322(5) 0.0309(5) 0.0515(6) 0.000 0.000 0.0060(4) C2 0.0354(5) 0.0330(5) 0.0550(6) 0.000 0.000 0.0061(4) C3 0.0293(4) 0.0380(5) 0.0642(7) 0.000 0.000 0.0081(4) C4 0.0285(4) 0.0311(5) 0.0464(5) 0.000 0.000 0.0036(4) C5 0.0349(5) 0.0332(5) 0.0533(6) 0.000 0.000 0.0059(4) C6 0.0485(7) 0.0283(5) 0.1088(10) 0.000 0.000 -0.0027(5) C7 0.0654(8) 0.0355(6) 0.1239(12) 0.000 0.000 0.0035(5) C8 0.0289(5) 0.0355(5) 0.0722(7) 0.000 0.000 0.0050(4) C9 0.0524(4) 0.0531(5) 0.0817(6) -0.0074(5) 0.0064(5) 0.0127(4) C10 0.0674(5) 0.0582(5) 0.1182(8) -0.0232(5) 0.0104(6) 0.0217(4) C11 0.0613(8) 0.0462(7) 0.1599(15) 0.000 0.000 0.0235(6) C12 0.0317(5) 0.0421(6) 0.0905(9) 0.000 0.000 0.0038(4) C13 0.0349(6) 0.0663(9) 0.227(2) 0.000 0.000 -0.0180(6) C14 0.0530(10) 0.0889(13) 0.339(4) 0.000 0.000 -0.0209(9) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C5 1.2124(13) . ? O2 C5 1.3260(12) . ? O2 C6 1.4494(13) . ? O3 C12 1.1869(14) . ? O4 C12 1.3279(14) . ? O4 C13 1.4786(16) . ? N1 C4 1.3520(12) . ? N1 C3 1.3704(13) . ? C1 C2 1.4191(14) . ? C1 C4 1.4195(14) . ? C1 C5 1.4569(14) . ? C2 C3 1.3730(14) . ? C2 C8 1.4881(14) . ? C3 C12 1.4734(15) . ? C4 C4 1.4620(18) 9_566 ? C6 C7 1.5138(17) . ? C8 C9 1.3790(11) . ? C8 C9 1.3790(11) 10_556 ? C9 C10 1.3835(12) . ? C10 C11 1.3719(14) . ? C11 C10 1.3719(14) 10_556 ? C13 C14 1.362(3) . ? 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 C5 O2 C6 117.72(8) . . ? C12 O4 C13 114.10(9) . . ? C4 N1 C3 110.95(8) . . ? C2 C1 C4 107.37(8) . . ? C2 C1 C5 124.84(9) . . ? C4 C1 C5 127.79(9) . . ? C3 C2 C1 106.92(9) . . ? C3 C2 C8 125.12(9) . . ? C1 C2 C8 127.97(9) . . ? N1 C3 C2 108.40(9) . . ? N1 C3 C12 122.79(9) . . ? C2 C3 C12 128.82(9) . . ? N1 C4 C1 106.37(8) . . ? N1 C4 C4 120.13(11) . 9_566 ? C1 C4 C4 133.50(11) . 9_566 ? O1 C5 O2 120.14(9) . . ? O1 C5 C1 127.36(9) . . ? O2 C5 C1 112.51(9) . . ? O2 C6 C7 105.36(9) . . ? C9 C8 C9 118.96(10) . 10_556 ? C9 C8 C2 120.50(5) . . ? C9 C8 C2 120.50(5) 10_556 . ? C8 C9 C10 120.52(10) . . ? C11 C10 C9 119.98(11) . . ? C10 C11 C10 120.01(13) 10_556 . ? O3 C12 O4 124.12(10) . . ? O3 C12 C3 123.59(10) . . ? O4 C12 C3 112.29(9) . . ? C14 C13 O4 112.19(13) . . ? _diffrn_measured_fraction_theta_max 0.969 _diffrn_reflns_theta_full 27.56 _diffrn_measured_fraction_theta_full 0.969 _refine_diff_density_max 0.302 _refine_diff_density_min -0.187 _refine_diff_density_rms 0.046