# Supplementary Material (ESI) for Perkin Transactions # This journal is © The Royal Society of Chemistry 2000 # CCDC Number: 207/382 data_10m _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C23 H20 N4 O2' _chemical_formula_weight 384.43 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0181 0.0091 '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' 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0492 0.0322 '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' _cell_length_a 5.1195(10) _cell_length_b 9.1710(18) _cell_length_c 21.063(4) _cell_angle_alpha 90.00 _cell_angle_beta 92.94(3) _cell_angle_gamma 90.00 _cell_volume 987.6(3) _cell_formula_units_Z 2 _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 1.293 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 404 _exptl_absorpt_coefficient_mu 0.685 _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 293(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Siemens P3' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count 97 _diffrn_standards_interval_time ? _diffrn_standards_decay_% 2% _diffrn_reflns_number 1940 _diffrn_reflns_av_R_equivalents 0.0398 _diffrn_reflns_av_sigmaI/netI 0.0434 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 0 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 2 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 2.10 _diffrn_reflns_theta_max 55.02 _reflns_number_total 1720 _reflns_number_gt 1432 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0605P)^2^+0.0799P] 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 -0.6(6) _refine_ls_number_reflns 1720 _refine_ls_number_parameters 262 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0609 _refine_ls_R_factor_gt 0.0483 _refine_ls_wR_factor_ref 0.1196 _refine_ls_wR_factor_gt 0.1119 _refine_ls_goodness_of_fit_ref 1.083 _refine_ls_restrained_S_all 1.083 _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 C1 C 0.5447(9) 0.6036(7) 0.8304(2) 0.0560(16) Uani 1 1 d . . . H1 H 0.6483 0.5842 0.7964 0.067 Uiso 1 1 calc R . . N2 N 0.5995(8) 0.7180(6) 0.86538(19) 0.0606(13) Uani 1 1 d . . . C3 C 0.4374(9) 0.7428(6) 0.9141(2) 0.0495(13) Uani 1 1 d . . . C4 C 0.4715(10) 0.8655(7) 0.9535(2) 0.0671(17) Uani 1 1 d . . . H4 H 0.6031 0.9326 0.9465 0.081 Uiso 1 1 calc R . . C5 C 0.3117(11) 0.8846(8) 1.0015(3) 0.0729(19) Uani 1 1 d . . . H5A H 0.3288 0.9656 1.0279 0.087 Uiso 1 1 calc R . . C6 C 0.1205(11) 0.7803(8) 1.0106(3) 0.075(2) Uani 1 1 d . . . H6 H 0.0133 0.7941 1.0444 0.090 Uiso 1 1 calc R . . N7 N 0.0792(8) 0.6654(6) 0.97566(19) 0.0669(14) Uani 1 1 d . . . C8 C 0.2358(9) 0.6460(6) 0.9257(2) 0.0482(13) Uani 1 1 d . . . N9 N 0.1863(7) 0.5265(5) 0.88890(17) 0.0466(10) Uani 1 1 d . . . C10 C 0.3376(8) 0.5083(6) 0.8415(2) 0.0424(13) Uani 1 1 d . . . C11 C 0.2826(8) 0.3758(6) 0.80021(19) 0.0427(13) Uani 1 1 d . . . H11 H 0.0994 0.3490 0.8050 0.051 Uiso 1 1 calc R . . C12 C 0.4484(9) 0.2454(6) 0.8221(2) 0.0472(13) Uani 1 1 d . . . H12A H 0.6296 0.2642 0.8135 0.057 Uiso 1 1 calc R . . H12B H 0.4382 0.2340 0.8677 0.057 Uiso 1 1 calc R . . C13 C 0.3635(9) 0.1066(6) 0.7901(2) 0.0484(14) Uani 1 1 d . . . C14 C 0.1603(11) 0.0256(7) 0.8123(3) 0.0698(17) Uani 1 1 d . . . H14 H 0.0800 0.0552 0.8487 0.084 Uiso 1 1 calc R . . C15 C 0.0743(12) -0.0999(8) 0.7805(4) 0.088(2) Uani 1 1 d . . . H15 H -0.0636 -0.1534 0.7957 0.106 Uiso 1 1 calc R . . C16 C 0.1921(14) -0.1452(8) 0.7268(4) 0.093(2) Uani 1 1 d . . . H16 H 0.1362 -0.2294 0.7055 0.111 Uiso 1 1 calc R . . C17 C 0.3899(15) -0.0653(9) 0.7056(3) 0.090(2) Uani 1 1 d . . . H17 H 0.4699 -0.0948 0.6691 0.108 Uiso 1 1 calc R . . C18 C 0.4768(11) 0.0586(7) 0.7364(2) 0.0636(16) Uani 1 1 d . . . H18 H 0.6149 0.1109 0.7206 0.076 Uiso 1 1 calc R . . N19 N 0.3110(6) 0.4069(5) 0.73344(14) 0.0417(11) Uani 1 1 d . . . H19 H 0.4647 0.4020 0.7189 0.050 Uiso 1 1 calc R . . O20 O -0.1164(5) 0.4470(5) 0.70710(14) 0.0652(12) Uani 1 1 d . . . C20 C 0.1132(8) 0.4422(6) 0.6939(2) 0.0438(12) Uani 1 1 d . . . O21 O 0.1940(5) 0.4778(4) 0.63590(13) 0.0547(11) Uani 1 1 d . . . C21 C 0.1349(8) 0.5831(6) 0.5339(2) 0.0458(13) Uani 1 1 d . . . C22 C -0.0003(9) 0.5294(8) 0.5903(2) 0.0687(19) Uani 1 1 d . . . H22A H -0.0998 0.6077 0.6084 0.082 Uiso 1 1 calc R . . H22B H -0.1198 0.4512 0.5780 0.082 Uiso 1 1 calc R . . C24 C 0.0515(10) 0.5429(8) 0.4731(2) 0.0639(17) Uani 1 1 d . . . H24A H -0.0882 0.4785 0.4676 0.077 Uiso 1 1 calc R . . C25 C 0.1685(13) 0.5950(9) 0.4204(2) 0.081(2) Uani 1 1 d . . . H25 H 0.1067 0.5676 0.3799 0.097 Uiso 1 1 calc R . . C26 C 0.3787(14) 0.6883(9) 0.4283(3) 0.083(2) Uani 1 1 d . . . H26 H 0.4602 0.7244 0.3931 0.100 Uiso 1 1 calc R . . C27 C 0.4651(12) 0.7268(7) 0.4873(3) 0.0751(18) Uani 1 1 d . . . H27 H 0.6084 0.7888 0.4926 0.090 Uiso 1 1 calc R . . C28 C 0.3450(10) 0.6761(7) 0.5402(3) 0.0621(15) Uani 1 1 d . . . H28 H 0.4071 0.7051 0.5805 0.075 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 C1 0.040(3) 0.076(5) 0.054(3) -0.006(3) 0.015(2) -0.009(3) N2 0.051(2) 0.070(4) 0.061(3) -0.010(3) 0.011(2) -0.014(3) C3 0.045(3) 0.052(3) 0.051(3) -0.008(3) 0.001(2) -0.002(3) C4 0.056(3) 0.061(4) 0.082(4) -0.016(4) -0.011(3) -0.005(3) C5 0.066(4) 0.075(5) 0.076(4) -0.030(4) -0.008(3) 0.018(4) C6 0.063(4) 0.095(6) 0.066(4) -0.025(4) 0.012(3) 0.009(4) N7 0.066(3) 0.078(4) 0.058(3) -0.022(3) 0.020(2) 0.004(3) C8 0.043(3) 0.056(4) 0.047(3) 0.002(3) 0.010(2) 0.007(3) N9 0.046(2) 0.050(3) 0.045(2) -0.002(2) 0.0151(17) 0.001(2) C10 0.036(2) 0.053(4) 0.039(2) 0.000(3) 0.008(2) 0.000(3) C11 0.031(2) 0.062(4) 0.035(2) 0.002(3) 0.0071(19) -0.004(3) C12 0.039(3) 0.054(4) 0.049(3) 0.003(3) 0.003(2) 0.004(3) C13 0.044(3) 0.048(4) 0.053(3) 0.006(3) 0.000(2) 0.005(3) C14 0.063(4) 0.058(4) 0.089(4) 0.016(4) 0.016(3) 0.000(4) C15 0.065(4) 0.058(5) 0.142(6) 0.023(5) -0.002(4) -0.020(4) C16 0.100(5) 0.051(4) 0.125(6) -0.012(5) -0.020(5) -0.002(5) C17 0.116(5) 0.070(5) 0.085(4) -0.021(4) 0.008(4) -0.004(5) C18 0.071(3) 0.060(4) 0.060(3) -0.012(3) 0.008(3) -0.011(3) N19 0.0263(18) 0.062(3) 0.0374(19) -0.001(2) 0.0086(15) 0.001(2) O20 0.0284(15) 0.110(4) 0.0584(19) 0.007(2) 0.0097(14) 0.002(2) C20 0.041(3) 0.047(3) 0.044(3) -0.002(3) 0.005(2) 0.004(3) O21 0.0398(16) 0.089(3) 0.0364(16) 0.0102(19) 0.0071(13) 0.007(2) C21 0.036(2) 0.056(3) 0.045(3) 0.005(3) 0.005(2) 0.006(3) C22 0.047(3) 0.106(6) 0.053(3) 0.016(3) -0.001(2) -0.006(4) C24 0.062(3) 0.074(5) 0.056(3) 0.005(3) 0.001(2) -0.006(4) C25 0.086(4) 0.113(6) 0.043(3) 0.008(4) 0.007(3) 0.001(5) C26 0.087(4) 0.101(6) 0.063(4) 0.022(4) 0.014(3) 0.004(5) C27 0.064(4) 0.072(5) 0.090(4) 0.015(4) 0.013(3) -0.012(4) C28 0.062(3) 0.065(4) 0.059(3) 0.001(3) -0.001(3) 0.009(3) _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 C1 N2 1.304(7) . ? C1 C10 1.403(7) . ? N2 C3 1.372(6) . ? C3 C8 1.392(7) . ? C3 C4 1.404(7) . ? C4 C5 1.343(7) . ? C5 C6 1.389(8) . ? C6 N7 1.296(8) . ? N7 C8 1.367(5) . ? C8 N9 1.358(6) . ? N9 C10 1.305(5) . ? C10 C11 1.512(7) . ? C11 N19 1.449(5) . ? C11 C12 1.525(7) . ? C12 C13 1.494(7) . ? C13 C18 1.370(6) . ? C13 C14 1.379(7) . ? C14 C15 1.392(9) . ? C15 C16 1.374(8) . ? C16 C17 1.345(9) . ? C17 C18 1.371(9) . ? N19 C20 1.318(5) . ? O20 C20 1.222(5) . ? C20 O21 1.350(5) . ? O21 C22 1.427(6) . ? C21 C28 1.374(7) . ? C21 C24 1.380(6) . ? C21 C22 1.489(6) . ? C24 C25 1.373(7) . ? C25 C26 1.378(9) . ? C26 C27 1.344(8) . ? C27 C28 1.379(8) . ? 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 N2 C1 C10 123.3(4) . . ? C1 N2 C3 115.8(4) . . ? N2 C3 C8 120.5(5) . . ? N2 C3 C4 120.9(5) . . ? C8 C3 C4 118.6(5) . . ? C5 C4 C3 119.1(6) . . ? C4 C5 C6 118.3(6) . . ? N7 C6 C5 125.3(5) . . ? C6 N7 C8 117.2(5) . . ? N9 C8 N7 116.4(5) . . ? N9 C8 C3 122.2(4) . . ? N7 C8 C3 121.4(5) . . ? C10 N9 C8 116.0(4) . . ? N9 C10 C1 122.1(5) . . ? N9 C10 C11 116.2(4) . . ? C1 C10 C11 121.7(4) . . ? N19 C11 C10 112.0(4) . . ? N19 C11 C12 111.5(4) . . ? C10 C11 C12 111.9(3) . . ? C13 C12 C11 112.8(4) . . ? C18 C13 C14 117.7(6) . . ? C18 C13 C12 121.4(5) . . ? C14 C13 C12 120.9(5) . . ? C13 C14 C15 120.5(6) . . ? C16 C15 C14 120.3(6) . . ? C17 C16 C15 118.6(7) . . ? C16 C17 C18 121.7(7) . . ? C13 C18 C17 121.1(6) . . ? C20 N19 C11 123.3(3) . . ? O20 C20 N19 125.6(4) . . ? O20 C20 O21 122.7(4) . . ? N19 C20 O21 111.7(3) . . ? C20 O21 C22 117.0(3) . . ? C28 C21 C24 117.3(5) . . ? C28 C21 C22 121.5(4) . . ? C24 C21 C22 121.2(5) . . ? O21 C22 C21 108.1(3) . . ? C25 C24 C21 122.0(6) . . ? C24 C25 C26 119.2(6) . . ? C27 C26 C25 119.5(6) . . ? C26 C27 C28 121.2(6) . . ? C21 C28 C27 120.8(5) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 55.02 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.173 _refine_diff_density_min -0.201 _refine_diff_density_rms 0.046