# Supplementary Material (ESI) for ChemComm # This journal is © The Royal Society of Chemistry 1999 # CCDC Number: 182/1375 data_99dai007 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H15 N5 O3' _chemical_formula_weight 349.35 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 P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 4.684(4) _cell_length_b 13.470(5) _cell_length_c 13.786(6) _cell_angle_alpha 73.144(10) _cell_angle_beta 78.90(2) _cell_angle_gamma 88.302(10) _cell_volume 816.6(8) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 15 _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.421 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 364 _exptl_absorpt_coefficient_mu 0.101 _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 150(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 'Nonius CAD4' _diffrn_measurement_method 'bisect mode' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 2307 _diffrn_reflns_av_R_equivalents 0.0696 _diffrn_reflns_av_sigmaI/netI 0.3223 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.53 _diffrn_reflns_theta_max 22.76 _reflns_number_total 2201 _reflns_number_gt 714 _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^)+(0.0327P)^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 2201 _refine_ls_number_parameters 247 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.2872 _refine_ls_R_factor_gt 0.0595 _refine_ls_wR_factor_ref 0.1412 _refine_ls_wR_factor_gt 0.0888 _refine_ls_goodness_of_fit_ref 0.914 _refine_ls_restrained_S_all 0.914 _refine_ls_shift/su_max 0.003 _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 0.1185(13) 0.3506(5) 0.3914(5) 0.0614(19) Uani 1 1 d . . . O2 O 0.6108(11) 0.4318(4) -0.1038(4) 0.0491(17) Uani 1 1 d . . . O3 O 0.1769(11) 0.0542(4) 0.0618(4) 0.0465(16) Uani 1 1 d . . . N1 N 0.4247(12) 0.2358(5) 0.1480(5) 0.0289(17) Uani 1 1 d . . . N2 N 0.1307(13) 0.3461(5) 0.2275(5) 0.0333(18) Uani 1 1 d . . . N3 N -0.0820(16) 0.4247(5) 0.2144(6) 0.0435(19) Uani 1 1 d D . . N4 N 0.2347(14) 0.3153(5) -0.0344(5) 0.0321(17) Uani 1 1 d . . . N5 N 0.4845(15) 0.1280(5) -0.0884(5) 0.0389(18) Uani 1 1 d D . . C1 C 0.5123(16) 0.1926(6) 0.2407(6) 0.033(2) Uani 1 1 d . . . C2 C 0.7002(17) 0.1088(6) 0.2490(7) 0.047(2) Uani 1 1 d . . . H2 H 0.7626 0.0827 0.1931 0.056 Uiso 1 1 calc R . . C3 C 0.7910(18) 0.0656(7) 0.3414(8) 0.058(3) Uani 1 1 d . . . H3 H 0.9124 0.0091 0.3475 0.070 Uiso 1 1 calc R . . C4 C 0.7058(19) 0.1042(7) 0.4260(7) 0.056(3) Uani 1 1 d . . . H4 H 0.7764 0.0756 0.4865 0.067 Uiso 1 1 calc R . . C5 C 0.5198(17) 0.1836(7) 0.4193(7) 0.046(2) Uani 1 1 d . . . H5 H 0.4609 0.2090 0.4757 0.055 Uiso 1 1 calc R . . C6 C 0.4153(16) 0.2277(6) 0.3283(6) 0.033(2) Uani 1 1 d . . . C7 C 0.2155(18) 0.3121(6) 0.3229(7) 0.039(2) Uani 1 1 d . . . C8 C 0.2381(16) 0.3096(6) 0.1438(6) 0.030(2) Uani 1 1 d . . . C9 C 0.1344(17) 0.3625(6) 0.0472(6) 0.036(2) Uani 1 1 d . . . H9A H -0.0767 0.3613 0.0614 0.044 Uiso 1 1 calc R . . H9B H 0.2012 0.4345 0.0239 0.044 Uiso 1 1 calc R . . C10 C 0.4713(19) 0.3566(6) -0.1072(6) 0.037(2) Uani 1 1 d . . . C11 C 0.5582(16) 0.3095(6) -0.1950(6) 0.032(2) Uani 1 1 d . . . C12 C 0.6623(18) 0.3796(7) -0.2917(6) 0.052(3) Uani 1 1 d . . . H12 H 0.6523 0.4506 -0.3003 0.062 Uiso 1 1 calc R . . C13 C 0.7810(19) 0.3430(8) -0.3752(7) 0.063(3) Uani 1 1 d . . . H13 H 0.8442 0.3895 -0.4401 0.076 Uiso 1 1 calc R . . C14 C 0.804(2) 0.2379(8) -0.3612(7) 0.068(3) Uani 1 1 d . . . H14 H 0.8943 0.2137 -0.4159 0.081 Uiso 1 1 calc R . . C15 C 0.6956(18) 0.1684(7) -0.2668(7) 0.055(3) Uani 1 1 d . . . H15 H 0.7061 0.0974 -0.2585 0.066 Uiso 1 1 calc R . . C16 C 0.5686(15) 0.2049(6) -0.1829(6) 0.034(2) Uani 1 1 d . . . C17 C 0.2483(18) 0.1271(7) -0.0150(7) 0.037(2) Uani 1 1 d . . . C18 C 0.0723(16) 0.2259(6) -0.0368(6) 0.040(2) Uani 1 1 d . . . H18A H 0.0204 0.2391 -0.1041 0.048 Uiso 1 1 calc R . . H18B H -0.1064 0.2159 0.0144 0.048 Uiso 1 1 calc R . . H01 H -0.171(18) 0.422(7) 0.286(2) 0.11(4) Uiso 1 1 d D . . H02 H 0.028(12) 0.491(3) 0.184(4) 0.03(2) Uiso 1 1 d D . . H03 H 0.570(16) 0.060(3) -0.080(6) 0.08(3) 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 0.076(5) 0.066(4) 0.047(4) -0.032(4) -0.003(4) 0.018(4) O2 0.032(4) 0.054(4) 0.067(5) -0.033(4) 0.001(3) -0.004(3) O3 0.051(4) 0.029(3) 0.048(4) -0.004(3) 0.008(3) -0.005(3) N1 0.019(4) 0.030(4) 0.035(5) -0.009(3) 0.001(3) -0.001(3) N2 0.030(4) 0.033(4) 0.037(5) -0.014(4) -0.003(4) 0.010(4) N3 0.051(5) 0.029(5) 0.050(6) -0.016(4) 0.000(4) 0.000(4) N4 0.032(5) 0.025(4) 0.041(5) -0.011(4) -0.010(4) 0.000(3) N5 0.042(5) 0.027(4) 0.045(5) -0.009(4) -0.002(4) -0.001(4) C1 0.038(6) 0.029(5) 0.026(6) 0.000(5) 0.002(5) -0.002(4) C2 0.045(6) 0.043(6) 0.049(7) -0.011(5) -0.004(5) 0.015(5) C3 0.050(7) 0.051(6) 0.064(7) -0.004(6) -0.008(6) 0.012(5) C4 0.057(7) 0.067(8) 0.046(7) -0.013(6) -0.020(6) 0.001(6) C5 0.034(6) 0.052(6) 0.059(7) -0.027(5) -0.008(5) -0.003(5) C6 0.035(6) 0.032(5) 0.028(6) -0.005(4) -0.001(5) -0.002(4) C7 0.041(6) 0.031(5) 0.045(7) -0.008(5) -0.009(5) -0.002(5) C8 0.027(5) 0.041(6) 0.023(5) -0.015(5) 0.002(4) 0.003(4) C9 0.050(6) 0.036(5) 0.026(5) -0.014(4) -0.007(4) 0.007(4) C10 0.039(6) 0.037(6) 0.039(6) -0.015(5) -0.015(5) 0.014(5) C11 0.029(5) 0.038(6) 0.024(5) -0.005(4) -0.004(4) 0.003(4) C12 0.060(7) 0.045(6) 0.040(6) -0.001(5) -0.004(5) -0.002(5) C13 0.074(8) 0.079(9) 0.024(6) -0.006(6) 0.005(5) -0.003(6) C14 0.084(8) 0.068(8) 0.051(8) -0.027(6) 0.003(6) 0.002(7) C15 0.067(7) 0.048(6) 0.056(7) -0.025(6) -0.007(6) -0.006(5) C16 0.026(5) 0.051(6) 0.027(6) -0.015(5) -0.002(4) -0.006(4) C17 0.041(6) 0.037(6) 0.040(6) -0.023(5) -0.011(5) -0.004(4) C18 0.037(6) 0.036(5) 0.049(6) -0.011(4) -0.014(5) 0.011(5) _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 C7 1.213(9) . ? O2 C10 1.239(8) . ? O3 C17 1.216(9) . ? N1 C8 1.300(8) . ? N1 C1 1.377(8) . ? N2 C8 1.384(8) . ? N2 C7 1.393(9) . ? N2 N3 1.430(8) . ? N4 C10 1.352(9) . ? N4 C9 1.443(8) . ? N4 C18 1.454(8) . ? N5 C17 1.345(9) . ? N5 C16 1.404(9) . ? C1 C2 1.403(10) . ? C1 C6 1.412(9) . ? C2 C3 1.381(10) . ? C3 C4 1.397(11) . ? C4 C5 1.352(10) . ? C5 C6 1.397(10) . ? C6 C7 1.446(10) . ? C8 C9 1.482(9) . ? C10 C11 1.507(9) . ? C11 C16 1.371(9) . ? C11 C12 1.397(10) . ? C12 C13 1.395(10) . ? C13 C14 1.376(11) . ? C14 C15 1.378(11) . ? C15 C16 1.407(10) . ? C17 C18 1.530(9) . ? 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 N1 C1 117.5(7) . . ? C8 N2 C7 124.9(7) . . ? C8 N2 N3 117.4(7) . . ? C7 N2 N3 117.8(7) . . ? C10 N4 C9 119.3(7) . . ? C10 N4 C18 122.1(7) . . ? C9 N4 C18 118.6(7) . . ? C17 N5 C16 127.0(7) . . ? N1 C1 C2 118.5(8) . . ? N1 C1 C6 122.7(7) . . ? C2 C1 C6 118.8(8) . . ? C3 C2 C1 118.9(9) . . ? C2 C3 C4 121.9(9) . . ? C5 C4 C3 119.5(9) . . ? C4 C5 C6 120.6(9) . . ? C5 C6 C1 120.2(8) . . ? C5 C6 C7 119.7(8) . . ? C1 C6 C7 120.0(8) . . ? O1 C7 N2 120.9(8) . . ? O1 C7 C6 126.8(9) . . ? N2 C7 C6 112.2(8) . . ? N1 C8 N2 122.6(7) . . ? N1 C8 C9 121.7(7) . . ? N2 C8 C9 115.7(7) . . ? N4 C9 C8 112.9(6) . . ? O2 C10 N4 121.7(7) . . ? O2 C10 C11 120.4(8) . . ? N4 C10 C11 117.8(8) . . ? C16 C11 C12 119.8(7) . . ? C16 C11 C10 124.2(7) . . ? C12 C11 C10 115.7(8) . . ? C13 C12 C11 120.0(8) . . ? C14 C13 C12 119.8(10) . . ? C13 C14 C15 120.4(10) . . ? C14 C15 C16 119.9(9) . . ? C11 C16 N5 124.5(7) . . ? C11 C16 C15 119.9(8) . . ? N5 C16 C15 115.4(8) . . ? O3 C17 N5 123.5(8) . . ? O3 C17 C18 122.3(8) . . ? N5 C17 C18 114.2(8) . . ? N4 C18 C17 111.8(6) . . ? 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 C8 N1 C1 C2 176.3(8) . . . . ? C8 N1 C1 C6 -2.2(10) . . . . ? N1 C1 C2 C3 179.5(8) . . . . ? C6 C1 C2 C3 -2.0(12) . . . . ? C1 C2 C3 C4 -1.3(13) . . . . ? C2 C3 C4 C5 2.7(14) . . . . ? C3 C4 C5 C6 -0.7(14) . . . . ? C4 C5 C6 C1 -2.6(12) . . . . ? C4 C5 C6 C7 179.7(8) . . . . ? N1 C1 C6 C5 -177.6(7) . . . . ? C2 C1 C6 C5 3.9(11) . . . . ? N1 C1 C6 C7 0.1(11) . . . . ? C2 C1 C6 C7 -178.4(7) . . . . ? C8 N2 C7 O1 177.4(8) . . . . ? N3 N2 C7 O1 -2.3(11) . . . . ? C8 N2 C7 C6 -4.4(10) . . . . ? N3 N2 C7 C6 175.9(7) . . . . ? C5 C6 C7 O1 -1.2(13) . . . . ? C1 C6 C7 O1 -179.0(9) . . . . ? C5 C6 C7 N2 -179.3(7) . . . . ? C1 C6 C7 N2 2.9(10) . . . . ? C1 N1 C8 N2 0.9(10) . . . . ? C1 N1 C8 C9 178.8(7) . . . . ? C7 N2 C8 N1 2.6(11) . . . . ? N3 N2 C8 N1 -177.6(7) . . . . ? C7 N2 C8 C9 -175.4(8) . . . . ? N3 N2 C8 C9 4.3(10) . . . . ? C10 N4 C9 C8 -97.7(8) . . . . ? C18 N4 C9 C8 83.8(8) . . . . ? N1 C8 C9 N4 6.9(11) . . . . ? N2 C8 C9 N4 -175.1(7) . . . . ? C9 N4 C10 O2 2.6(11) . . . . ? C18 N4 C10 O2 -178.9(7) . . . . ? C9 N4 C10 C11 -176.1(6) . . . . ? C18 N4 C10 C11 2.3(10) . . . . ? O2 C10 C11 C16 136.6(8) . . . . ? N4 C10 C11 C16 -44.7(11) . . . . ? O2 C10 C11 C12 -36.5(11) . . . . ? N4 C10 C11 C12 142.3(7) . . . . ? C16 C11 C12 C13 -1.1(12) . . . . ? C10 C11 C12 C13 172.2(8) . . . . ? C11 C12 C13 C14 -2.2(14) . . . . ? C12 C13 C14 C15 3.9(15) . . . . ? C13 C14 C15 C16 -2.2(14) . . . . ? C12 C11 C16 N5 176.5(8) . . . . ? C10 C11 C16 N5 3.7(12) . . . . ? C12 C11 C16 C15 2.8(11) . . . . ? C10 C11 C16 C15 -170.0(8) . . . . ? C17 N5 C16 C11 42.7(12) . . . . ? C17 N5 C16 C15 -143.3(8) . . . . ? C14 C15 C16 C11 -1.2(13) . . . . ? C14 C15 C16 N5 -175.4(8) . . . . ? C16 N5 C17 O3 174.3(8) . . . . ? C16 N5 C17 C18 -5.0(12) . . . . ? C10 N4 C18 C17 68.7(9) . . . . ? C9 N4 C18 C17 -112.8(8) . . . . ? O3 C17 C18 N4 114.3(9) . . . . ? N5 C17 C18 N4 -66.3(9) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 22.76 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.253 _refine_diff_density_min -0.249 _refine_diff_density_rms 0.064