# Supplementary Material (ESI) for ChemComm # This journal is © The Royal Society of Chemistry 2000 # CCDC Number: 182/1692 data_s92 _audit_creation_method SHELXL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C22 H20 N2 O3' _chemical_formula_weight 360.40 _chemical_melting_point ? _chemical_compound_source ? 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 ? _symmetry_space_group_name_H-M ? 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 9.372(8) _cell_length_b 11.198(7) _cell_length_c 17.679(7) _cell_angle_alpha 90.00 _cell_angle_beta 101.07(4) _cell_angle_gamma 90.00 _cell_volume 1820.8(21) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.315 _exptl_crystal_density_method ? _exptl_crystal_F_000 760 _exptl_absorpt_coefficient_mu 0.088 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device ? _diffrn_measurement_method ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6955 _diffrn_reflns_av_R_equivalents 0.1123 _diffrn_reflns_av_sigmaI/netI 0.2330 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.16 _diffrn_reflns_theta_max 24.90 _reflns_number_total 2655 _reflns_number_observed 945 _reflns_observed_criterion >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-92 (Sheldrick, 1993)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement on F^2^ for ALL reflections except for 0 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R- factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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 w=1/[\s^2^(Fo^2^)+(0.0218P)^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 ? _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2655 _refine_ls_number_parameters 248 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1370 _refine_ls_R_factor_obs 0.0380 _refine_ls_wR_factor_all 0.0830 _refine_ls_wR_factor_obs 0.0676 _refine_ls_goodness_of_fit_all 0.542 _refine_ls_goodness_of_fit_obs 0.816 _refine_ls_restrained_S_all 0.542 _refine_ls_restrained_S_obs 0.816 _refine_ls_shift/esd_max 0.000 _refine_ls_shift/esd_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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group O1 O 0.1375(2) -0.2495(2) 0.73687(13) 0.0499(7) Uani 1 d . . O2 O 0.4260(2) 0.2198(2) 0.58110(13) 0.0525(7) Uani 1 d . . O3 O 0.6473(2) 0.1355(2) 0.59827(15) 0.0684(8) Uani 1 d . . N1 N 0.1868(3) 0.4764(3) 0.5257(2) 0.0806(12) Uani 1 d . . N2 N -0.0886(3) 0.2810(3) 0.5630(2) 0.0617(9) Uani 1 d . . H2A H -0.1707(3) 0.2517(3) 0.5687(2) 0.071(3) Uiso 1 calc R . H2B H -0.0838(3) 0.3535(3) 0.5476(2) 0.071(3) Uiso 1 calc R . C1 C 0.1962(3) -0.1395(3) 0.7246(2) 0.0430(10) Uani 1 d . . C2 C 0.3133(3) -0.0951(3) 0.7871(2) 0.0561(11) Uani 1 d . . H2C H 0.3933(10) -0.1502(10) 0.7945(9) 0.113(6) Uiso 1 calc R . H2D H 0.2767(7) -0.0881(19) 0.8340(4) 0.113(6) Uiso 1 calc R . H2E H 0.3458(17) -0.0184(9) 0.7730(6) 0.113(6) Uiso 1 calc R . C3 C 0.0317(3) -0.2731(3) 0.6729(2) 0.0471(10) Uani 1 d . . C4 C -0.0437(3) -0.3915(3) 0.6738(2) 0.0700(12) Uani 1 d . . H4A H -0.0661(20) -0.4049(9) 0.7238(4) 0.113(6) Uiso 1 calc R . H4B H 0.0189(10) -0.4540(4) 0.6622(12) 0.113(6) Uiso 1 calc R . H4C H -0.1319(13) -0.3912(8) 0.6358(9) 0.113(6) Uiso 1 calc R . C5 C 0.0208(3) -0.1826(3) 0.6241(2) 0.0457(10) Uani 1 d . . H5 H -0.0442(3) -0.1766(3) 0.5773(2) 0.071(3) Uiso 1 calc R . C6 C 0.1262(3) -0.0962(3) 0.6558(2) 0.0391(9) Uani 1 d . . C7 C 0.1483(3) 0.0205(3) 0.6214(2) 0.0415(9) Uani 1 d . . C8 C 0.0283(3) 0.0944(3) 0.6035(2) 0.0448(10) Uani 1 d . . H8 H -0.0617(3) 0.0638(3) 0.6085(2) 0.071(3) Uiso 1 calc R . C10 C 0.0343(3) 0.2124(3) 0.5784(2) 0.0428(10) Uani 1 d . . C12 C 0.1707(3) 0.2584(3) 0.5702(2) 0.0410(9) Uani 1 d . . C13 C 0.1840(3) 0.3792(4) 0.5464(2) 0.0522(11) Uani 1 d . . C14 C 0.2872(3) 0.1819(3) 0.5857(2) 0.0400(9) Uani 1 d . . C15 C 0.5210(4) 0.1223(3) 0.6018(2) 0.0496(10) Uani 1 d . . C16 C 0.2835(3) 0.0644(3) 0.6076(2) 0.0393(9) Uani 1 d . . C17 C 0.4334(3) 0.0181(3) 0.6173(2) 0.0401(9) Uani 1 d . . C18 C 0.4907(3) -0.0948(3) 0.6235(2) 0.0420(9) Uani 1 d . . C19 C 0.6487(3) -0.1148(3) 0.6511(2) 0.0501(10) Uani 1 d . . H19 H 0.7007(3) -0.1440(3) 0.6117(2) 0.071(3) Uiso 1 calc R . C20 C 0.7380(3) -0.0430(4) 0.7131(2) 0.0670(12) Uani 1 d . . H20A H 0.8378(3) -0.0266(4) 0.7089(2) 0.071(3) Uiso 1 calc R . H20B H 0.6902(3) 0.0214(4) 0.7352(2) 0.071(3) Uiso 1 calc R . C21 C 0.7013(3) -0.1666(4) 0.7315(2) 0.0705(13) Uani 1 d . . H21A H 0.6303(3) -0.1778(4) 0.7641(2) 0.071(3) Uiso 1 calc R . H21B H 0.7782(3) -0.2259(4) 0.7378(2) 0.071(3) Uiso 1 calc R . C22 C 0.4004(3) -0.2003(3) 0.6009(2) 0.0495(10) Uani 1 d . . H22 H 0.3029(3) -0.1820(3) 0.5718(2) 0.071(3) Uiso 1 calc R . C23 C 0.4654(4) -0.3133(3) 0.5750(2) 0.0631(12) Uani 1 d . . H23A H 0.4104(4) -0.3549(3) 0.5307(2) 0.071(3) Uiso 1 calc R . H23B H 0.5701(4) -0.3160(3) 0.5792(2) 0.071(3) Uiso 1 calc R . C24 C 0.4089(4) -0.3156(3) 0.6463(2) 0.0654(12) Uani 1 d . . H24A H 0.4786(4) -0.3198(3) 0.6945(2) 0.071(3) Uiso 1 calc R . H24B H 0.3189(4) -0.3587(3) 0.6460(2) 0.071(3) Uiso 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 0.0502(14) 0.049(2) 0.051(2) 0.0064(14) 0.0119(12) -0.0033(12) O2 0.0401(15) 0.046(2) 0.071(2) 0.0107(14) 0.0096(12) -0.0014(12) O3 0.0363(13) 0.072(2) 0.098(2) 0.013(2) 0.0164(13) -0.0076(13) N1 0.064(2) 0.054(3) 0.123(3) 0.019(3) 0.014(2) -0.004(2) N2 0.046(2) 0.054(2) 0.087(3) 0.017(2) 0.019(2) 0.004(2) C1 0.042(2) 0.038(3) 0.054(3) 0.008(2) 0.022(2) -0.005(2) C2 0.046(2) 0.064(3) 0.055(3) 0.005(2) 0.001(2) -0.004(2) C3 0.044(2) 0.045(3) 0.052(3) 0.000(2) 0.009(2) -0.008(2) C4 0.072(2) 0.052(3) 0.084(3) 0.010(3) 0.010(2) -0.013(2) C5 0.038(2) 0.050(3) 0.049(3) 0.010(2) 0.009(2) -0.007(2) C6 0.031(2) 0.038(3) 0.052(3) 0.009(2) 0.017(2) -0.001(2) C7 0.039(2) 0.044(3) 0.041(2) 0.002(2) 0.006(2) 0.002(2) C8 0.036(2) 0.047(3) 0.053(3) 0.011(2) 0.013(2) 0.003(2) C10 0.036(2) 0.048(3) 0.046(3) 0.009(2) 0.012(2) 0.007(2) C12 0.035(2) 0.040(3) 0.047(3) 0.002(2) 0.007(2) -0.002(2) C13 0.041(2) 0.053(3) 0.062(3) 0.005(3) 0.008(2) -0.002(2) C14 0.030(2) 0.044(3) 0.048(3) 0.006(2) 0.011(2) -0.010(2) C15 0.044(2) 0.055(3) 0.050(3) 0.005(2) 0.010(2) -0.004(2) C16 0.033(2) 0.041(3) 0.045(2) 0.008(2) 0.013(2) -0.003(2) C17 0.034(2) 0.040(3) 0.049(3) 0.001(2) 0.012(2) -0.004(2) C18 0.036(2) 0.052(3) 0.039(2) 0.004(2) 0.011(2) -0.002(2) C19 0.033(2) 0.067(3) 0.050(3) -0.003(2) 0.009(2) 0.005(2) C20 0.040(2) 0.090(4) 0.072(3) 0.005(3) 0.013(2) 0.000(2) C21 0.049(2) 0.094(4) 0.070(3) 0.024(3) 0.014(2) 0.009(2) C22 0.042(2) 0.049(3) 0.059(3) -0.004(2) 0.013(2) 0.002(2) C23 0.060(2) 0.058(3) 0.078(3) -0.010(3) 0.029(2) 0.000(2) C24 0.070(3) 0.050(3) 0.077(3) 0.008(3) 0.018(2) -0.006(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C3 1.379(4) . ? O1 C1 1.383(3) . ? O2 C14 1.386(3) . ? O2 C15 1.412(4) . ? O3 C15 1.206(3) . ? N1 C13 1.151(4) . ? N2 C10 1.367(3) . ? C1 C6 1.357(4) . ? C1 C2 1.485(4) . ? C3 C5 1.323(4) . ? C3 C4 1.504(4) . ? C5 C6 1.419(4) . ? C6 C7 1.473(4) . ? C7 C8 1.383(4) . ? C7 C16 1.422(4) . ? C8 C10 1.398(4) . ? C10 C12 1.412(4) . ? C12 C14 1.374(4) . ? C12 C13 1.429(5) . ? C14 C16 1.374(4) . ? C15 C17 1.483(4) . ? C16 C17 1.477(4) . ? C17 C18 1.369(4) . ? C18 C22 1.464(4) . ? C18 C19 1.484(4) . ? C19 C20 1.483(4) . ? C19 C21 1.527(5) . ? C20 C21 1.478(5) . ? C22 C23 1.512(4) . ? C22 C24 1.514(4) . ? C23 C24 1.458(5) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C3 O1 C1 106.7(3) . . ? C14 O2 C15 107.4(3) . . ? C6 C1 O1 108.7(3) . . ? C6 C1 C2 135.1(3) . . ? O1 C1 C2 116.2(3) . . ? C5 C3 O1 109.9(3) . . ? C5 C3 C4 134.8(3) . . ? O1 C3 C4 115.2(3) . . ? C3 C5 C6 107.7(3) . . ? C1 C6 C5 106.9(3) . . ? C1 C6 C7 127.3(3) . . ? C5 C6 C7 125.8(3) . . ? C8 C7 C16 117.8(3) . . ? C8 C7 C6 116.9(3) . . ? C16 C7 C6 125.3(3) . . ? C7 C8 C10 123.9(3) . . ? N2 C10 C8 120.7(3) . . ? N2 C10 C12 121.3(3) . . ? C8 C10 C12 118.0(3) . . ? C14 C12 C10 116.9(3) . . ? C14 C12 C13 122.5(3) . . ? C10 C12 C13 120.5(3) . . ? N1 C13 C12 176.3(4) . . ? C12 C14 C16 126.2(3) . . ? C12 C14 O2 121.1(3) . . ? C16 C14 O2 112.7(3) . . ? O3 C15 O2 117.9(3) . . ? O3 C15 C17 133.6(3) . . ? O2 C15 C17 108.3(3) . . ? C14 C16 C7 116.8(3) . . ? C14 C16 C17 107.1(3) . . ? C7 C16 C17 135.9(3) . . ? C18 C17 C16 133.1(3) . . ? C18 C17 C15 121.3(3) . . ? C16 C17 C15 104.5(3) . . ? C17 C18 C22 121.8(3) . . ? C17 C18 C19 121.1(3) . . ? C22 C18 C19 117.1(3) . . ? C20 C19 C18 123.1(3) . . ? C20 C19 C21 58.8(2) . . ? C18 C19 C21 119.1(3) . . ? C21 C20 C19 62.1(2) . . ? C20 C21 C19 59.1(2) . . ? C18 C22 C23 120.8(3) . . ? C18 C22 C24 125.1(3) . . ? C23 C22 C24 57.6(2) . . ? C24 C23 C22 61.3(2) . . ? C23 C24 C22 61.1(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 C3 O1 C1 C6 1.1(3) . . . . ? C3 O1 C1 C2 179.8(3) . . . . ? C1 O1 C3 C5 -1.7(4) . . . . ? C1 O1 C3 C4 178.5(3) . . . . ? O1 C3 C5 C6 1.5(4) . . . . ? C4 C3 C5 C6 -178.6(4) . . . . ? O1 C1 C6 C5 -0.2(4) . . . . ? C2 C1 C6 C5 -178.5(3) . . . . ? O1 C1 C6 C7 176.8(3) . . . . ? C2 C1 C6 C7 -1.4(6) . . . . ? C3 C5 C6 C1 -0.8(4) . . . . ? C3 C5 C6 C7 -177.9(3) . . . . ? C1 C6 C7 C8 -122.0(3) . . . . ? C5 C6 C7 C8 54.5(5) . . . . ? C1 C6 C7 C16 55.7(5) . . . . ? C5 C6 C7 C16 -127.8(3) . . . . ? C16 C7 C8 C10 -5.1(5) . . . . ? C6 C7 C8 C10 172.8(3) . . . . ? C7 C8 C10 N2 -178.9(3) . . . . ? C7 C8 C10 C12 0.7(5) . . . . ? N2 C10 C12 C14 -178.9(3) . . . . ? C8 C10 C12 C14 1.6(5) . . . . ? N2 C10 C12 C13 1.0(5) . . . . ? C8 C10 C12 C13 -178.6(3) . . . . ? C14 C12 C13 N1 159.3(68) . . . . ? C10 C12 C13 N1 -20.5(71) . . . . ? C10 C12 C14 C16 0.8(5) . . . . ? C13 C12 C14 C16 -179.0(3) . . . . ? C10 C12 C14 O2 -178.3(3) . . . . ? C13 C12 C14 O2 1.9(5) . . . . ? C15 O2 C14 C12 178.8(3) . . . . ? C15 O2 C14 C16 -0.5(4) . . . . ? C14 O2 C15 O3 176.9(3) . . . . ? C14 O2 C15 C17 1.9(3) . . . . ? C12 C14 C16 C7 -5.3(5) . . . . ? O2 C14 C16 C7 174.0(3) . . . . ? C12 C14 C16 C17 179.6(3) . . . . ? O2 C14 C16 C17 -1.2(4) . . . . ? C8 C7 C16 C14 7.0(5) . . . . ? C6 C7 C16 C14 -170.7(3) . . . . ? C8 C7 C16 C17 -179.7(4) . . . . ? C6 C7 C16 C17 2.6(6) . . . . ? C14 C16 C17 C18 -165.2(4) . . . . ? C7 C16 C17 C18 21.1(7) . . . . ? C14 C16 C17 C15 2.2(4) . . . . ? C7 C16 C17 C15 -171.5(4) . . . . ? O3 C15 C17 C18 -7.1(6) . . . . ? O2 C15 C17 C18 166.7(3) . . . . ? O3 C15 C17 C16 -176.4(4) . . . . ? O2 C15 C17 C16 -2.5(4) . . . . ? C16 C17 C18 C22 16.6(6) . . . . ? C15 C17 C18 C22 -149.1(3) . . . . ? C16 C17 C18 C19 -165.5(3) . . . . ? C15 C17 C18 C19 28.8(5) . . . . ? C17 C18 C19 C20 37.7(5) . . . . ? C22 C18 C19 C20 -144.3(4) . . . . ? C17 C18 C19 C21 107.5(4) . . . . ? C22 C18 C19 C21 -74.5(4) . . . . ? C18 C19 C20 C21 106.5(4) . . . . ? C21 C19 C20 C21 0.0 . . . . ? C19 C20 C21 C19 0.0 . . . . ? C20 C19 C21 C20 0.0 . . . . ? C18 C19 C21 C20 -113.2(4) . . . . ? C17 C18 C22 C23 153.3(4) . . . . ? C19 C18 C22 C23 -24.6(5) . . . . ? C17 C18 C22 C24 -136.8(4) . . . . ? C19 C18 C22 C24 45.3(5) . . . . ? C18 C22 C23 C24 114.5(4) . . . . ? C24 C22 C23 C24 0.000(2) . . . . ? C22 C23 C24 C22 0.000(2) . . . . ? C18 C22 C24 C23 -107.2(4) . . . . ? C23 C22 C24 C23 0.000(1) . . . . ? _refine_diff_density_max 0.195 _refine_diff_density_min -0.198 _refine_diff_density_rms 0.061