# Supplementary Material (ESI) for Journal of Materials Chemistry # This journal is © The Royal Society of Chemistry 2000 # CCDC Number: 1145/263 data_a _audit_creation_method SHELXL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C15 H19 N3 O2' _chemical_formula_weight 273.33 _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 orthorhombic _symmetry_space_group_name_H-M Pna2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' 'x+1/2, -y+1/2, z' '-x+1/2, y+1/2, z+1/2' _cell_length_a 7.991(2) _cell_length_b 26.326(5) _cell_length_c 6.5880(13) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1385.9(5) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 24 _cell_measurement_theta_min 10 _cell_measurement_theta_max 11 _exptl_crystal_description plate _exptl_crystal_colour 'light yellow ' _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.2 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.310 _exptl_crystal_density_method ? _exptl_crystal_F_000 584 _exptl_absorpt_coefficient_mu 0.089 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(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 'Enraf Nonius CAD4' _diffrn_measurement_method \q/2\q _diffrn_standards_number 2 _diffrn_standards_interval_count 98 _diffrn_standards_interval_time ? _diffrn_standards_decay_% 4 _diffrn_reflns_number 2051 _diffrn_reflns_av_R_equivalents 0.1229 _diffrn_reflns_av_sigmaI/netI 0.3648 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 31 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 7 _diffrn_reflns_theta_min 2.66 _diffrn_reflns_theta_max 24.96 _reflns_number_total 1322 _reflns_number_observed 329 _reflns_observed_criterion >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXTL PLUS 5' _computing_structure_refinement 'SHELXTL PLUS 5' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement on F^2^ for ALL reflections except for 37 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^)+(0.0143P)^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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 4.63(539) _refine_ls_number_reflns 1285 _refine_ls_number_parameters 181 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.3264 _refine_ls_R_factor_obs 0.0659 _refine_ls_wR_factor_all 0.2310 _refine_ls_wR_factor_obs 0.0701 _refine_ls_goodness_of_fit_all 0.863 _refine_ls_goodness_of_fit_obs 1.360 _refine_ls_restrained_S_all 1.796 _refine_ls_restrained_S_obs 1.355 _refine_ls_shift/esd_max 0.042 _refine_ls_shift/esd_mean 0.011 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 -0.4215(14) 0.7376(4) -0.0728(16) 0.091(5) Uani 1 d . . O2 O -0.3768(15) 0.8118(5) -0.2028(14) 0.101(5) Uani 1 d . . N1 N -0.0959(14) 0.8592(4) 0.2755(20) 0.065(4) Uani 1 d . . N2 N 0.0382(13) 0.8365(4) 0.5712(16) 0.049(3) Uani 1 d . . H2N H 0.0503(13) 0.8142(4) 0.6656(16) 0.059 Uiso 1 calc R . N3 N -0.3548(15) 0.7785(7) -0.0813(23) 0.068(5) Uani 1 d . . C1 C -0.0650(18) 0.8231(5) 0.4283(23) 0.047(4) Uani 1 d . . C2 C -0.1272(17) 0.7734(5) 0.4129(25) 0.059(4) Uani 1 d . . H2A H -0.0947(17) 0.7490(5) 0.5072(25) 0.071 Uiso 1 calc R . C3 C -0.2325(17) 0.7609(6) 0.2643(24) 0.071(5) Uani 1 d . . H3A H -0.2864(17) 0.7295(6) 0.2623(24) 0.085 Uiso 1 calc R . C4 C -0.2590(22) 0.7974(6) 0.1093(25) 0.051(4) Uani 1 d . . C5 C -0.1952(17) 0.8441(6) 0.1183(28) 0.073(6) Uani 1 d . . H5A H -0.2191(17) 0.8671(6) 0.0148(28) 0.088 Uiso 1 calc R . C6 C 0.1369(17) 0.8823(6) 0.6000(20) 0.041(4) Uani 1 d . . C7 C 0.2580(16) 0.8905(5) 0.4264(21) 0.060(4) Uani 1 d . . H7A H 0.1954(16) 0.8946(5) 0.3014(21) 0.072 Uiso 1 calc R . H7B H 0.3282(16) 0.8607(5) 0.4122(21) 0.072 Uiso 1 calc R . C8 C 0.3693(17) 0.9371(6) 0.4585(25) 0.054(4) Uani 1 d . . H8A H 0.4440(17) 0.9420(6) 0.3422(25) 0.065 Uiso 1 calc R . C9 C 0.2606(19) 0.9824(6) 0.4872(17) 0.066(5) Uani 1 d . . H9A H 0.1969(19) 0.9884(6) 0.3642(17) 0.080 Uiso 1 calc R . H9B H 0.3300(19) 1.0120(6) 0.5119(17) 0.080 Uiso 1 calc R . C10 C 0.1412(19) 0.9753(6) 0.6636(23) 0.061(4) Uani 1 d . . H10A H 0.0706(19) 1.0055(6) 0.6798(23) 0.073 Uiso 1 calc R . C11 C 0.2488(17) 0.9667(6) 0.8574(18) 0.063(5) Uani 1 d . . H11A H 0.3209(17) 0.9958(6) 0.8803(18) 0.075 Uiso 1 calc R . H11B H 0.1765(17) 0.9628(6) 0.9747(18) 0.075 Uiso 1 calc R . C12 C 0.3508(17) 0.9207(6) 0.8298(18) 0.052(4) Uani 1 d . . H12A H 0.4147(17) 0.9150(6) 0.9547(18) 0.063 Uiso 1 calc R . C13 C 0.2434(18) 0.8742(5) 0.7913(17) 0.055(4) Uani 1 d . . H13A H 0.1710(18) 0.8683(5) 0.9070(17) 0.066 Uiso 1 calc R . H13B H 0.3143(18) 0.8447(5) 0.7737(17) 0.066 Uiso 1 calc R . C14 C 0.4733(14) 0.9281(6) 0.6579(23) 0.062(4) Uani 1 d . . H14A H 0.5433(14) 0.8982(6) 0.6432(23) 0.075 Uiso 1 calc R . H14B H 0.5447(14) 0.9571(6) 0.6849(23) 0.075 Uiso 1 calc R . C15 C 0.0316(14) 0.9278(5) 0.6328(25) 0.059(4) Uani 1 d . . H15A H -0.0384(14) 0.9227(5) 0.7513(25) 0.071 Uiso 1 calc R . H15B H -0.0410(14) 0.9327(5) 0.5164(25) 0.071 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 0.141(12) 0.098(10) 0.035(7) -0.019(8) -0.009(8) -0.062(8) O2 0.158(13) 0.091(9) 0.055(8) -0.004(9) -0.054(9) 0.014(8) N1 0.069(10) 0.060(9) 0.067(8) 0.005(10) -0.011(9) 0.007(7) N2 0.056(9) 0.056(9) 0.036(7) 0.027(7) -0.013(7) -0.006(7) N3 0.041(8) 0.112(14) 0.050(10) -0.017(12) -0.012(9) 0.007(9) C1 0.059(10) 0.029(9) 0.052(10) 0.001(9) 0.015(10) -0.021(9) C2 0.063(10) 0.033(9) 0.080(12) 0.026(10) 0.011(12) -0.005(8) C3 0.038(10) 0.057(11) 0.117(15) -0.041(13) 0.000(12) -0.022(9) C4 0.086(12) 0.038(9) 0.027(8) -0.006(8) -0.008(10) 0.010(9) C5 0.083(14) 0.065(12) 0.071(13) 0.018(13) -0.049(12) -0.032(10) C6 0.053(10) 0.056(10) 0.014(7) -0.006(8) -0.002(9) -0.003(9) C7 0.053(10) 0.090(12) 0.037(8) -0.004(10) -0.026(10) -0.011(10) C8 0.043(10) 0.077(11) 0.044(10) -0.001(11) -0.001(9) -0.003(10) C9 0.077(14) 0.093(14) 0.029(10) -0.010(9) -0.001(10) -0.021(12) C10 0.086(12) 0.048(10) 0.048(9) -0.013(10) -0.023(10) 0.023(10) C11 0.076(13) 0.077(12) 0.035(9) 0.000(9) 0.003(10) 0.005(12) C12 0.071(12) 0.077(12) 0.009(8) 0.008(8) -0.001(9) -0.016(11) C13 0.106(13) 0.045(9) 0.014(7) 0.011(8) -0.004(10) -0.031(10) C14 0.050(9) 0.072(11) 0.064(11) -0.014(9) -0.023(11) -0.006(10) C15 0.068(11) 0.060(10) 0.049(10) -0.003(9) -0.005(11) -0.026(10) _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 N3 1.20(2) . ? O2 N3 1.20(2) . ? N1 C5 1.36(2) . ? N1 C1 1.41(2) . ? N2 C1 1.30(2) . ? N2 C6 1.454(15) . ? N3 C4 1.55(2) . ? C1 C2 1.40(2) . ? C2 C3 1.33(2) . ? C3 C4 1.42(2) . ? C4 C5 1.33(2) . ? C6 C15 1.478(15) . ? C6 C7 1.51(2) . ? C6 C13 1.54(2) . ? C7 C8 1.53(2) . ? C8 C9 1.49(2) . ? C8 C14 1.57(2) . ? C9 C10 1.51(2) . ? C10 C15 1.54(2) . ? C10 C11 1.56(2) . ? C11 C12 1.47(2) . ? C12 C14 1.51(2) . ? C12 C13 1.52(2) . ? 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 N1 C1 116.7(12) . . ? C1 N2 C6 131.5(12) . . ? O1 N3 O2 128.3(17) . . ? O1 N3 C4 117.9(16) . . ? O2 N3 C4 112.2(14) . . ? N2 C1 C2 122.0(16) . . ? N2 C1 N1 116.5(11) . . ? C2 C1 N1 121.1(16) . . ? C3 C2 C1 120.5(16) . . ? C2 C3 C4 117.1(14) . . ? C5 C4 C3 122.5(16) . . ? C5 C4 N3 121.4(16) . . ? C3 C4 N3 116.0(13) . . ? C4 C5 N1 121.6(16) . . ? N2 C6 C15 112.5(12) . . ? N2 C6 C7 111.5(11) . . ? C15 C6 C7 111.0(13) . . ? N2 C6 C13 107.0(12) . . ? C15 C6 C13 107.9(12) . . ? C7 C6 C13 106.6(11) . . ? C6 C7 C8 112.4(13) . . ? C9 C8 C7 108.7(13) . . ? C9 C8 C14 108.9(13) . . ? C7 C8 C14 107.5(13) . . ? C8 C9 C10 111.5(13) . . ? C9 C10 C15 110.9(14) . . ? C9 C10 C11 107.4(12) . . ? C15 C10 C11 107.6(13) . . ? C12 C11 C10 109.0(11) . . ? C11 C12 C14 110.3(12) . . ? C11 C12 C13 111.8(12) . . ? C14 C12 C13 110.2(12) . . ? C12 C13 C6 109.9(12) . . ? C12 C14 C8 107.7(9) . . ? C6 C15 C10 110.7(11) . . ? _refine_diff_density_max 0.178 _refine_diff_density_min -0.148 _refine_diff_density_rms 0.041 data_admn-3 _audit_creation_method SHELXL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C15 H19 N3 O2' _chemical_formula_weight 273.33 _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 Orthorhombic _symmetry_space_group_name_H-M Pca2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' 'x+1/2, -y, z' '-x+1/2, y, z+1/2' _cell_length_a 28.310(10) _cell_length_b 6.612(2) _cell_length_c 7.474(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1398.9(7) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 24 _cell_measurement_theta_min 10 _cell_measurement_theta_max 11 _exptl_crystal_description prism _exptl_crystal_colour yellow _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.298 _exptl_crystal_density_method ? _exptl_crystal_F_000 584 _exptl_absorpt_coefficient_mu 0.088 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(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 'Siemens P3/PC' _diffrn_measurement_method '\w scans' _diffrn_standards_number 2 _diffrn_standards_interval_count 98 _diffrn_standards_interval_time ? _diffrn_standards_decay_% 5 _diffrn_reflns_number 1685 _diffrn_reflns_av_R_equivalents 0.0082 _diffrn_reflns_av_sigmaI/netI 0.2217 _diffrn_reflns_limit_h_min -3 _diffrn_reflns_limit_h_max 36 _diffrn_reflns_limit_k_min -1 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 1.44 _diffrn_reflns_theta_max 27.05 _reflns_number_total 1645 _reflns_number_observed 565 _reflns_observed_criterion >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXTL PLUS 5' _computing_structure_refinement 'SHELXTL PLUS 5' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement on F^2^ for ALL reflections except for 63 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^)+(0.0600P)^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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 1.18(641) _refine_ls_number_reflns 1582 _refine_ls_number_parameters 185 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.2874 _refine_ls_R_factor_obs 0.0719 _refine_ls_wR_factor_all 0.4079 _refine_ls_wR_factor_obs 0.1218 _refine_ls_goodness_of_fit_all 1.008 _refine_ls_goodness_of_fit_obs 1.247 _refine_ls_restrained_S_all 2.281 _refine_ls_restrained_S_obs 1.245 _refine_ls_shift/esd_max -0.010 _refine_ls_shift/esd_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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group O1 O 0.2338(3) 0.0214(11) -0.1578(12) 0.085(3) Uani 1 d . . O2 O 0.3051(2) -0.0944(11) -0.1562(11) 0.077(2) Uani 1 d . . N1 N 0.3530(3) 0.3870(11) 0.1241(12) 0.054(2) Uani 1 d . . N2 N 0.3357(3) 0.6932(12) 0.2683(11) 0.050(2) Uani 1 d . . H2N H 0.3096(30) 0.8090(134) 0.2720(132) 0.085(35) Uiso 1 d . . N3 N 0.2760(3) 0.0380(13) -0.1205(11) 0.055(2) Uani 1 d . . C1 C 0.3225(3) 0.5357(14) 0.1667(11) 0.045(2) Uani 1 d . . C2 C 0.2747(3) 0.5324(14) 0.1038(14) 0.051(3) Uani 1 d . . H2B H 0.2547(3) 0.6411(14) 0.1263(14) 0.062 Uiso 1 calc R . C3 C 0.2588(3) 0.3703(13) 0.0116(12) 0.050(2) Uani 1 d . . H3A H 0.2275(3) 0.3621(13) -0.0250(12) 0.060 Uiso 1 calc R . C4 C 0.2908(3) 0.2156(14) -0.0272(13) 0.044(2) Uani 1 d . . C5 C 0.3371(3) 0.2373(15) 0.0289(11) 0.051(3) Uani 1 d . . H5A H 0.3585(3) 0.1371(15) -0.0041(11) 0.062 Uiso 1 calc R . C6 C 0.3802(3) 0.7154(12) 0.3703(12) 0.042(2) Uani 1 d . . C7 C 0.3761(3) 0.9213(12) 0.4679(13) 0.044(2) Uani 1 d . . H7A H 0.3731(3) 1.0297(12) 0.3811(13) 0.053 Uiso 1 calc R . H7B H 0.3483(3) 0.9222(12) 0.5437(13) 0.053 Uiso 1 calc R . C8 C 0.4207(3) 0.9532(14) 0.5821(12) 0.056(3) Uani 1 d . . H8A H 0.4180(3) 1.0820(14) 0.6461(12) 0.067 Uiso 1 calc R . C9 C 0.4640(3) 0.9598(13) 0.4626(15) 0.058(3) Uani 1 d . . H9A H 0.4610(3) 1.0682(13) 0.3759(15) 0.069 Uiso 1 calc R . H9B H 0.4921(3) 0.9843(13) 0.5339(15) 0.069 Uiso 1 calc R . C10 C 0.4681(3) 0.7586(13) 0.3676(14) 0.054(3) Uani 1 d . . H10A H 0.4960(3) 0.7618(13) 0.2905(14) 0.065 Uiso 1 calc R . C11 C 0.4239(3) 0.7238(15) 0.2490(13) 0.056(3) Uani 1 d . . H11A H 0.4207(3) 0.8333(15) 0.1634(13) 0.067 Uiso 1 calc R . H11B H 0.4270(3) 0.5980(15) 0.1834(13) 0.067 Uiso 1 calc R . C12 C 0.3857(3) 0.5459(12) 0.5067(14) 0.053(3) Uani 1 d . . H12A H 0.3880(3) 0.4172(12) 0.4451(14) 0.064 Uiso 1 calc R . H12B H 0.3582(3) 0.5419(12) 0.5836(14) 0.064 Uiso 1 calc R . C13 C 0.4303(3) 0.5787(14) 0.6213(14) 0.057(3) Uani 1 d . . H13A H 0.4338(3) 0.4684(14) 0.7079(14) 0.068 Uiso 1 calc R . C14 C 0.4254(3) 0.7815(17) 0.7189(12) 0.064(3) Uani 1 d . . H14A H 0.4529(3) 0.8043(17) 0.7936(12) 0.077 Uiso 1 calc R . H14B H 0.3977(3) 0.7787(17) 0.7954(12) 0.077 Uiso 1 calc R . C15 C 0.4734(3) 0.5881(14) 0.4983(14) 0.060(3) Uani 1 d . . H15A H 0.5017(3) 0.6081(14) 0.5692(14) 0.072 Uiso 1 calc R . H15B H 0.4765(3) 0.4614(14) 0.4341(14) 0.072 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 0.056(5) 0.082(6) 0.117(6) -0.003(5) -0.035(5) -0.024(4) O2 0.067(5) 0.080(5) 0.084(6) -0.026(5) 0.001(4) -0.011(4) N1 0.042(4) 0.051(4) 0.068(6) -0.013(5) -0.004(5) 0.009(4) N2 0.040(4) 0.052(5) 0.059(6) -0.002(5) -0.013(5) 0.014(4) N3 0.064(7) 0.054(6) 0.048(5) 0.001(5) -0.002(5) -0.011(5) C1 0.056(6) 0.045(5) 0.034(5) 0.000(5) -0.011(5) 0.005(5) C2 0.041(6) 0.059(6) 0.054(6) 0.003(7) -0.006(5) 0.014(5) C3 0.036(5) 0.065(6) 0.049(6) -0.002(6) -0.007(5) -0.003(5) C4 0.044(5) 0.046(5) 0.041(5) -0.003(5) -0.010(5) -0.017(5) C5 0.056(6) 0.058(6) 0.040(6) -0.017(5) -0.003(5) 0.001(6) C6 0.058(6) 0.039(5) 0.030(5) 0.009(5) -0.007(5) 0.004(4) C7 0.040(5) 0.043(5) 0.048(6) -0.009(5) -0.004(5) 0.006(4) C8 0.062(7) 0.047(6) 0.059(6) -0.013(6) -0.022(6) -0.007(5) C9 0.047(6) 0.054(6) 0.071(7) -0.011(6) 0.011(6) -0.011(5) C10 0.048(6) 0.068(7) 0.047(6) 0.003(6) -0.003(5) -0.012(5) C11 0.061(7) 0.055(7) 0.050(6) 0.001(6) -0.004(6) 0.013(5) C12 0.049(6) 0.035(5) 0.075(7) -0.003(6) -0.009(6) 0.003(4) C13 0.060(7) 0.056(6) 0.055(6) 0.013(7) -0.029(6) 0.002(5) C14 0.043(6) 0.106(9) 0.042(6) -0.016(7) -0.010(5) -0.007(6) C15 0.040(5) 0.066(7) 0.073(7) -0.002(7) -0.014(6) -0.006(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 N3 1.232(9) . ? O2 N3 1.232(9) . ? N1 C5 1.300(10) . ? N1 C1 1.346(10) . ? N2 C1 1.341(10) . ? N2 C6 1.481(11) . ? N2 H2N 1.06(9) . ? N3 C4 1.429(11) . ? C1 C2 1.434(12) . ? C2 C3 1.350(11) . ? C2 H2B 0.93 . ? C3 C4 1.396(11) . ? C3 H3A 0.93 . ? C4 C5 1.384(12) . ? C5 H5A 0.93 . ? C6 C12 1.523(11) . ? C6 C11 1.533(12) . ? C6 C7 1.549(10) . ? C7 C8 1.540(11) . ? C7 H7A 0.97 . ? C7 H7B 0.97 . ? C8 C9 1.516(12) . ? C8 C14 1.533(12) . ? C8 H8A 0.98 . ? C9 C10 1.512(11) . ? C9 H9A 0.97 . ? C9 H9B 0.97 . ? C10 C15 1.499(11) . ? C10 C11 1.551(13) . ? C10 H10A 0.98 . ? C11 H11A 0.97 . ? C11 H11B 0.97 . ? C12 C13 1.540(12) . ? C12 H12A 0.97 . ? C12 H12B 0.97 . ? C13 C15 1.528(12) . ? C13 C14 1.532(12) . ? C13 H13A 0.98 . ? C14 H14A 0.97 . ? C14 H14B 0.97 . ? C15 H15A 0.97 . ? C15 H15B 0.97 . ? 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 N1 C1 117.6(8) . . ? C1 N2 C6 127.2(8) . . ? C1 N2 H2N 112.5(49) . . ? C6 N2 H2N 120.3(50) . . ? O2 N3 O1 122.5(9) . . ? O2 N3 C4 119.6(8) . . ? O1 N3 C4 117.9(9) . . ? N2 C1 N1 121.6(8) . . ? N2 C1 C2 117.3(8) . . ? N1 C1 C2 121.1(9) . . ? C3 C2 C1 119.5(8) . . ? C3 C2 H2B 120.2(5) . . ? C1 C2 H2B 120.2(6) . . ? C2 C3 C4 118.2(8) . . ? C2 C3 H3A 120.9(5) . . ? C4 C3 H3A 120.9(5) . . ? C5 C4 C3 118.3(8) . . ? C5 C4 N3 120.7(9) . . ? C3 C4 N3 121.0(8) . . ? N1 C5 C4 125.0(9) . . ? N1 C5 H5A 117.5(5) . . ? C4 C5 H5A 117.5(6) . . ? N2 C6 C12 111.0(8) . . ? N2 C6 C11 112.7(7) . . ? C12 C6 C11 109.9(8) . . ? N2 C6 C7 105.4(7) . . ? C12 C6 C7 109.8(7) . . ? C11 C6 C7 107.9(7) . . ? C8 C7 C6 108.6(7) . . ? C8 C7 H7A 110.0(5) . . ? C6 C7 H7A 110.0(4) . . ? C8 C7 H7B 110.0(5) . . ? C6 C7 H7B 110.0(5) . . ? H7A C7 H7B 108.3 . . ? C9 C8 C14 110.1(9) . . ? C9 C8 C7 109.9(8) . . ? C14 C8 C7 109.8(8) . . ? C9 C8 H8A 109.0(5) . . ? C14 C8 H8A 109.0(5) . . ? C7 C8 H8A 109.0(5) . . ? C10 C9 C8 108.2(8) . . ? C10 C9 H9A 110.1(6) . . ? C8 C9 H9A 110.1(6) . . ? C10 C9 H9B 110.1(5) . . ? C8 C9 H9B 110.1(6) . . ? H9A C9 H9B 108.4 . . ? C15 C10 C9 111.3(8) . . ? C15 C10 C11 110.0(8) . . ? C9 C10 C11 109.7(8) . . ? C15 C10 H10A 108.6(5) . . ? C9 C10 H10A 108.6(5) . . ? C11 C10 H10A 108.6(6) . . ? C6 C11 C10 108.5(8) . . ? C6 C11 H11A 110.0(5) . . ? C10 C11 H11A 110.0(5) . . ? C6 C11 H11B 110.0(5) . . ? C10 C11 H11B 110.0(5) . . ? H11A C11 H11B 108.4 . . ? C6 C12 C13 110.7(8) . . ? C6 C12 H12A 109.5(5) . . ? C13 C12 H12A 109.5(5) . . ? C6 C12 H12B 109.5(5) . . ? C13 C12 H12B 109.5(6) . . ? H12A C12 H12B 108.1 . . ? C15 C13 C14 108.8(8) . . ? C15 C13 C12 109.0(9) . . ? C14 C13 C12 108.3(8) . . ? C15 C13 H13A 110.2(5) . . ? C14 C13 H13A 110.2(5) . . ? C12 C13 H13A 110.2(5) . . ? C13 C14 C8 109.8(7) . . ? C13 C14 H14A 109.7(5) . . ? C8 C14 H14A 109.7(5) . . ? C13 C14 H14B 109.7(5) . . ? C8 C14 H14B 109.7(5) . . ? H14A C14 H14B 108.2 . . ? C10 C15 C13 110.0(8) . . ? C10 C15 H15A 109.7(5) . . ? C13 C15 H15A 109.7(5) . . ? C10 C15 H15B 109.7(5) . . ? C13 C15 H15B 109.7(5) . . ? H15A C15 H15B 108.2 . . ? _refine_diff_density_max 0.182 _refine_diff_density_min -0.223 _refine_diff_density_rms 0.048 data_conp-lt _audit_creation_method SHELXL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C13 H19 N3 O2' _chemical_formula_weight 249.31 _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 orthorhombic _symmetry_space_group_name_H-M Pca2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' 'x+1/2, -y, z' '-x+1/2, y, z+1/2' _cell_length_a 26.099(5) _cell_length_b 6.637(2) _cell_length_c 7.555(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1308.7(6) _cell_formula_units_Z 4 _cell_measurement_temperature 167(2) _cell_measurement_reflns_used 24 _cell_measurement_theta_min 11 _cell_measurement_theta_max 12 _exptl_crystal_description prism _exptl_crystal_colour yellow _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.4 _exptl_crystal_size_min 0.2 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.265 _exptl_crystal_density_method ? _exptl_crystal_F_000 536 _exptl_absorpt_coefficient_mu 0.087 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 167(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 'Siemens PC/P3' _diffrn_measurement_method \q/2\q _diffrn_standards_number 2 _diffrn_standards_interval_count 98 _diffrn_standards_interval_time ? _diffrn_standards_decay_% 3 _diffrn_reflns_number 1622 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0861 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_h_max 33 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -7 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 1.56 _diffrn_reflns_theta_max 27.55 _reflns_number_total 1622 _reflns_number_observed 909 _reflns_observed_criterion >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXTL PLUS 5' _computing_structure_refinement 'SHELXTL PLUS 5' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement on F^2^ for ALL reflections except for 52 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^)+(0.0642P)^2^+0.0840P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.99(283) _refine_ls_number_reflns 1570 _refine_ls_number_parameters 163 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.1519 _refine_ls_R_factor_obs 0.0592 _refine_ls_wR_factor_all 0.1637 _refine_ls_wR_factor_obs 0.1082 _refine_ls_goodness_of_fit_all 1.021 _refine_ls_goodness_of_fit_obs 1.205 _refine_ls_restrained_S_all 1.322 _refine_ls_restrained_S_obs 1.204 _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 0.21452(11) 0.3980(4) 0.3630(4) 0.0514(8) Uani 1 d . . O2 O 0.29037(12) 0.2811(5) 0.3174(5) 0.0646(10) Uani 1 d . . N1 N 0.35612(10) 0.7405(5) 0.5898(4) 0.0336(7) Uani 1 d . . N2 N 0.34621(10) 1.0442(4) 0.7356(4) 0.0321(8) Uani 1 d . . H2A H 0.32667(10) 1.1489(4) 0.7589(4) 0.039 Uiso 1 calc R . N3 N 0.26187(13) 0.4114(5) 0.3754(4) 0.0381(8) Uani 1 d . . C1 C 0.32538(13) 0.8939(5) 0.6425(4) 0.0282(8) Uani 1 d . . C2 C 0.27190(12) 0.8945(5) 0.6073(5) 0.0308(8) Uani 1 d . . H2B H 0.25123(12) 1.0037(5) 0.6462(5) 0.037 Uiso 1 calc R . C3 C 0.2506(2) 0.7391(5) 0.5184(5) 0.0321(8) Uani 1 d . . H3A H 0.2150(2) 0.7368(5) 0.4929(5) 0.038 Uiso 1 calc R . C4 C 0.28262(14) 0.5819(5) 0.4653(5) 0.0303(8) Uani 1 d . . C5 C 0.33446(14) 0.5917(5) 0.5008(5) 0.0319(9) Uani 1 d . . H5A H 0.35572(14) 0.4858(5) 0.4589(5) 0.038 Uiso 1 calc R . C6 C 0.39916(14) 1.0488(5) 0.8022(5) 0.0309(9) Uani 1 d . . H6A H 0.42225(14) 0.9984(5) 0.7062(5) 0.037 Uiso 1 calc R . C7 C 0.41202(14) 1.2693(6) 0.8362(6) 0.0439(10) Uani 1 d . . H7A H 0.40564(14) 1.3450(6) 0.7255(6) 0.053 Uiso 1 calc R . H7B H 0.38776(14) 1.3210(6) 0.9261(6) 0.053 Uiso 1 calc R . C8 C 0.4660(2) 1.3182(7) 0.8982(6) 0.0499(11) Uani 1 d . . H8A H 0.4702(2) 1.4663(7) 0.8938(6) 0.060 Uiso 1 calc R . H8B H 0.4903(2) 1.2599(7) 0.8113(6) 0.060 Uiso 1 calc R . C9 C 0.48228(14) 1.2475(8) 1.0818(6) 0.0574(13) Uani 1 d . . H9A H 0.49297(14) 1.1047(8) 1.0730(6) 0.069 Uiso 1 calc R . H9B H 0.51273(14) 1.3263(8) 1.1180(6) 0.069 Uiso 1 calc R . C10 C 0.4426(2) 1.2642(8) 1.2264(7) 0.0615(14) Uani 1 d . . H10A H 0.4599(2) 1.3116(8) 1.3352(7) 0.074 Uiso 1 calc R . H10B H 0.4177(2) 1.3695(8) 1.1915(7) 0.074 Uiso 1 calc R . C11 C 0.4132(2) 1.0764(7) 1.2713(6) 0.0568(12) Uani 1 d . . H11A H 0.3919(2) 1.1062(7) 1.3767(6) 0.068 Uiso 1 calc R . H11B H 0.4383(2) 0.9722(7) 1.3067(6) 0.068 Uiso 1 calc R . C12 C 0.37795(15) 0.9832(7) 1.1306(6) 0.0443(10) Uani 1 d . . H12A H 0.35194(15) 1.0849(7) 1.0971(6) 0.053 Uiso 1 calc R . H12B H 0.35956(15) 0.8684(7) 1.1850(6) 0.053 Uiso 1 calc R . C13 C 0.40425(14) 0.9080(6) 0.9605(5) 0.0379(10) Uani 1 d . . H13A H 0.44111(14) 0.8874(6) 0.9855(5) 0.045 Uiso 1 calc R . H13B H 0.38950(14) 0.7755(6) 0.9284(5) 0.045 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 0.047(2) 0.050(2) 0.057(2) -0.007(2) -0.011(2) -0.0146(15) O2 0.067(2) 0.050(2) 0.078(2) -0.034(2) -0.004(2) 0.003(2) N1 0.035(2) 0.037(2) 0.029(2) -0.003(2) 0.003(2) 0.0014(15) N2 0.028(2) 0.032(2) 0.037(2) -0.008(2) -0.0041(15) 0.0040(12) N3 0.050(2) 0.034(2) 0.031(2) 0.001(2) -0.007(2) -0.003(2) C1 0.033(2) 0.034(2) 0.018(2) -0.001(2) -0.001(2) 0.000(2) C2 0.032(2) 0.031(2) 0.029(2) -0.003(2) -0.002(2) 0.005(2) C3 0.028(2) 0.040(2) 0.028(2) 0.003(2) -0.002(2) -0.004(2) C4 0.038(2) 0.030(2) 0.023(2) -0.002(2) -0.003(2) -0.002(2) C5 0.043(2) 0.028(2) 0.024(2) -0.007(2) 0.000(2) 0.004(2) C6 0.032(2) 0.032(2) 0.029(2) -0.004(2) -0.004(2) 0.0010(15) C7 0.045(2) 0.047(2) 0.040(2) 0.010(2) -0.008(2) -0.004(2) C8 0.041(2) 0.058(3) 0.051(3) 0.004(2) -0.003(2) -0.011(2) C9 0.032(2) 0.091(4) 0.050(3) -0.013(3) -0.006(2) -0.015(2) C10 0.053(3) 0.089(4) 0.042(3) -0.016(3) -0.003(2) -0.026(3) C11 0.053(3) 0.081(3) 0.036(2) -0.009(3) -0.006(2) -0.004(2) C12 0.045(2) 0.051(2) 0.037(2) 0.005(2) -0.004(2) -0.016(2) C13 0.036(2) 0.040(2) 0.037(2) -0.001(2) -0.011(2) 0.000(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 N3 1.242(4) . ? O2 N3 1.222(4) . ? N1 C5 1.322(4) . ? N1 C1 1.356(4) . ? N2 C1 1.336(4) . ? N2 C6 1.471(4) . ? N3 C4 1.427(5) . ? C1 C2 1.421(5) . ? C2 C3 1.351(5) . ? C3 C4 1.396(5) . ? C4 C5 1.381(5) . ? C6 C7 1.523(5) . ? C6 C13 1.524(5) . ? C7 C8 1.520(5) . ? C8 C9 1.525(6) . ? C9 C10 1.510(6) . ? C10 C11 1.503(6) . ? C11 C12 1.535(6) . ? C12 C13 1.540(6) . ? 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 N1 C1 117.2(3) . . ? C1 N2 C6 125.3(3) . . ? O2 N3 O1 121.9(3) . . ? O2 N3 C4 120.1(3) . . ? O1 N3 C4 118.0(3) . . ? N2 C1 N1 118.3(3) . . ? N2 C1 C2 119.7(3) . . ? N1 C1 C2 121.9(3) . . ? C3 C2 C1 119.7(3) . . ? C2 C3 C4 117.8(4) . . ? C5 C4 C3 119.7(3) . . ? C5 C4 N3 120.1(3) . . ? C3 C4 N3 120.2(3) . . ? N1 C5 C4 123.6(3) . . ? N2 C6 C7 106.5(3) . . ? N2 C6 C13 109.7(3) . . ? C7 C6 C13 115.9(3) . . ? C8 C7 C6 117.5(3) . . ? C7 C8 C9 118.2(4) . . ? C10 C9 C8 116.4(4) . . ? C11 C10 C9 117.0(4) . . ? C10 C11 C12 118.9(4) . . ? C11 C12 C13 116.2(3) . . ? C6 C13 C12 114.7(3) . . ? _refine_diff_density_max 0.172 _refine_diff_density_min -0.182 _refine_diff_density_rms 0.045 data_conp-0 _audit_creation_method SHELXL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C13 H19 N3 O2' _chemical_formula_weight 249.31 _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 orthorhombic _symmetry_space_group_name_H-M Pca2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' 'x+1/2, -y, z' '-x+1/2, y, z+1/2' _cell_length_a 26.285(5) _cell_length_b 6.6470(10) _cell_length_c 7.631(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1333.3(5) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 24 _cell_measurement_theta_min 11 _cell_measurement_theta_max 12 _exptl_crystal_description prism _exptl_crystal_colour yellow _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.4 _exptl_crystal_size_min 0.2 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.242 _exptl_crystal_density_method ? _exptl_crystal_F_000 536 _exptl_absorpt_coefficient_mu 0.086 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _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 'Siemens PC/P3' _diffrn_measurement_method \q/2\q _diffrn_standards_number 2 _diffrn_standards_interval_count 98 _diffrn_standards_interval_time ? _diffrn_standards_decay_% 3 _diffrn_reflns_number 1657 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0560 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 34 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 3.06 _diffrn_reflns_theta_max 27.57 _reflns_number_total 1657 _reflns_number_observed 857 _reflns_observed_criterion >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXTL PLUS 5' _computing_structure_refinement 'SHELXTL PLUS 5' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement on F^2^ for ALL reflections except for 50 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^)+(0.1017P)^2^+0.2890P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -1.28(470) _refine_ls_number_reflns 1607 _refine_ls_number_parameters 163 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.1729 _refine_ls_R_factor_obs 0.0736 _refine_ls_wR_factor_all 0.2592 _refine_ls_wR_factor_obs 0.1673 _refine_ls_goodness_of_fit_all 1.068 _refine_ls_goodness_of_fit_obs 1.238 _refine_ls_restrained_S_all 1.347 _refine_ls_restrained_S_obs 1.237 _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 0.2151(2) 0.4011(6) 0.3679(7) 0.0948(15) Uani 1 d . . O2 O 0.2899(2) 0.2865(7) 0.3206(9) 0.113(2) Uani 1 d . . N1 N 0.35537(15) 0.7420(6) 0.5890(6) 0.0624(12) Uani 1 d . . N2 N 0.3467(2) 1.0441(6) 0.7352(6) 0.0630(12) Uani 1 d . . H2A H 0.3281(2) 1.1480(6) 0.7559(6) 0.076 Uiso 1 calc R . N3 N 0.2612(2) 0.4142(7) 0.3797(7) 0.0725(13) Uani 1 d . . C1 C 0.3252(2) 0.8925(8) 0.6437(6) 0.0559(12) Uani 1 d . . C2 C 0.2724(2) 0.8953(8) 0.6112(7) 0.0586(13) Uani 1 d . . H2B H 0.2525(2) 1.0020(8) 0.6505(7) 0.070 Uiso 1 calc R . C3 C 0.2507(2) 0.7403(7) 0.5217(7) 0.0587(12) Uani 1 d . . H3A H 0.2161(2) 0.7392(7) 0.4969(7) 0.070 Uiso 1 calc R . C4 C 0.2822(2) 0.5843(8) 0.4690(7) 0.0566(12) Uani 1 d . . C5 C 0.3337(2) 0.5940(7) 0.5022(7) 0.0640(14) Uani 1 d . . H5A H 0.3542(2) 0.4902(7) 0.4611(7) 0.077 Uiso 1 calc R . C6 C 0.3984(2) 1.0467(8) 0.8018(9) 0.0657(14) Uani 1 d . . H6A H 0.4204(2) 0.9935(8) 0.7090(9) 0.079 Uiso 1 calc R . C7 C 0.4130(2) 1.2649(9) 0.8291(11) 0.090(2) Uani 1 d . . H7A H 0.4085(2) 1.3348(9) 0.7186(11) 0.108 Uiso 1 calc R . H7B H 0.3893(2) 1.3232(9) 0.9120(11) 0.108 Uiso 1 calc R . C8 C 0.4660(3) 1.3074(13) 0.8933(12) 0.105(2) Uani 1 d . . H8A H 0.4891(3) 1.2304(13) 0.8205(12) 0.126 Uiso 1 calc R . H8B H 0.4729(3) 1.4483(13) 0.8704(12) 0.126 Uiso 1 calc R . C9 C 0.4797(3) 1.2691(24) 1.0739(16) 0.179(5) Uani 1 d . . H9A H 0.5049(3) 1.3697(24) 1.1052(16) 0.214 Uiso 1 calc R . H9B H 0.4971(3) 1.1404(24) 1.0754(16) 0.214 Uiso 1 calc R . C10 C 0.4423(3) 1.2640(19) 1.2186(12) 0.142(4) Uani 1 d . . H10A H 0.4606(3) 1.3001(19) 1.3244(12) 0.170 Uiso 1 calc R . H10B H 0.4183(3) 1.3718(19) 1.1965(12) 0.170 Uiso 1 calc R . C11 C 0.4128(3) 1.0877(13) 1.2597(11) 0.113(3) Uani 1 d . . H11A H 0.3911(3) 1.1228(13) 1.3580(11) 0.135 Uiso 1 calc R . H11B H 0.4364(3) 0.9866(13) 1.3017(11) 0.135 Uiso 1 calc R . C12 C 0.3789(2) 0.9856(11) 1.1242(10) 0.089(2) Uani 1 d . . H12A H 0.3625(2) 0.8719(11) 1.1804(10) 0.106 Uiso 1 calc R . H12B H 0.3524(2) 1.0797(11) 1.0914(10) 0.106 Uiso 1 calc R . C13 C 0.4040(2) 0.9103(8) 0.9571(9) 0.077(2) Uani 1 d . . H13B H 0.4400(2) 0.8907(8) 0.9797(9) 0.093 Uiso 1 calc R . H13C H 0.3896(2) 0.7802(8) 0.9278(9) 0.093 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 0.087(3) 0.082(3) 0.115(4) -0.015(3) -0.011(3) -0.027(2) O2 0.112(4) 0.084(3) 0.143(5) -0.055(4) -0.010(4) 0.000(3) N1 0.055(2) 0.060(2) 0.072(3) -0.011(2) -0.004(2) 0.005(2) N2 0.060(2) 0.056(2) 0.074(3) -0.012(2) -0.010(2) 0.004(2) N3 0.085(4) 0.061(3) 0.072(3) -0.002(3) -0.009(3) -0.008(3) C1 0.056(3) 0.060(3) 0.052(3) 0.002(3) 0.000(2) 0.009(3) C2 0.058(3) 0.061(3) 0.057(3) -0.004(3) -0.005(2) 0.001(2) C3 0.054(2) 0.066(3) 0.057(3) 0.004(3) -0.008(2) 0.002(3) C4 0.066(3) 0.052(2) 0.052(3) 0.002(2) -0.009(2) -0.006(2) C5 0.069(4) 0.057(3) 0.067(4) -0.011(3) 0.003(3) 0.013(2) C6 0.056(3) 0.071(3) 0.071(3) -0.007(3) -0.005(3) -0.001(2) C7 0.094(5) 0.081(4) 0.095(5) 0.025(4) -0.028(4) -0.024(3) C8 0.083(5) 0.116(5) 0.115(6) 0.003(5) -0.002(4) -0.038(4) C9 0.079(5) 0.327(16) 0.129(9) -0.063(10) -0.009(6) -0.064(8) C10 0.106(6) 0.211(11) 0.108(6) -0.064(7) -0.010(5) -0.075(7) C11 0.105(6) 0.147(7) 0.087(5) -0.029(6) -0.010(4) -0.008(5) C12 0.091(5) 0.088(4) 0.086(4) 0.007(4) -0.004(4) -0.026(4) C13 0.076(4) 0.063(3) 0.092(5) -0.002(4) -0.021(3) -0.002(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 O1 N3 1.217(6) . ? O2 N3 1.222(7) . ? N1 C5 1.316(6) . ? N1 C1 1.343(6) . ? N2 C1 1.350(6) . ? N2 C6 1.451(7) . ? N3 C4 1.430(7) . ? C1 C2 1.411(7) . ? C2 C3 1.360(7) . ? C3 C4 1.385(7) . ? C4 C5 1.380(7) . ? C6 C13 1.500(8) . ? C6 C7 1.515(8) . ? C7 C8 1.502(9) . ? C8 C9 1.447(15) . ? C9 C10 1.479(13) . ? C10 C11 1.441(13) . ? C11 C12 1.523(10) . ? C12 C13 1.520(10) . ? 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 N1 C1 117.3(4) . . ? C1 N2 C6 125.5(4) . . ? O1 N3 O2 122.4(5) . . ? O1 N3 C4 118.3(5) . . ? O2 N3 C4 119.2(5) . . ? N1 C1 N2 118.1(4) . . ? N1 C1 C2 122.4(5) . . ? N2 C1 C2 119.5(5) . . ? C3 C2 C1 119.3(5) . . ? C2 C3 C4 117.6(5) . . ? C5 C4 C3 119.8(5) . . ? C5 C4 N3 120.2(5) . . ? C3 C4 N3 120.0(5) . . ? N1 C5 C4 123.5(5) . . ? N2 C6 C13 111.3(5) . . ? N2 C6 C7 107.3(4) . . ? C13 C6 C7 116.4(5) . . ? C8 C7 C6 117.4(6) . . ? C9 C8 C7 120.6(7) . . ? C8 C9 C10 123.3(9) . . ? C11 C10 C9 122.7(9) . . ? C10 C11 C12 122.0(8) . . ? C13 C12 C11 117.6(5) . . ? C6 C13 C12 114.9(5) . . ? _refine_diff_density_max 0.194 _refine_diff_density_min -0.189 _refine_diff_density_rms 0.045 data_AANP-LT _audit_creation_method SHELXL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C15 H19 N3 O2' _chemical_formula_weight 273.33 _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 orthorhombic _symmetry_space_group_name_H-M Pca2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' 'x+1/2, -y, z' '-x+1/2, y, z+1/2' _cell_length_a 28.158(6) _cell_length_b 6.584(2) _cell_length_c 7.3950(10) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1371.0(5) _cell_formula_units_Z 4 _cell_measurement_temperature 163(2) _cell_measurement_reflns_used 24 _cell_measurement_theta_min 13 _cell_measurement_theta_max 14 _exptl_crystal_description prism _exptl_crystal_colour yellow _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.2 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.324 _exptl_crystal_density_method ? _exptl_crystal_F_000 584 _exptl_absorpt_coefficient_mu 0.090 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 163(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 'Siemens P3/PC' _diffrn_measurement_method \q/2\q _diffrn_standards_number 2 _diffrn_standards_interval_count 98 _diffrn_standards_interval_time ? _diffrn_standards_decay_% 3 _diffrn_reflns_number 4242 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0521 _diffrn_reflns_limit_h_min -29 _diffrn_reflns_limit_h_max 48 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -6 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 1.45 _diffrn_reflns_theta_max 40.09 _reflns_number_total 4242 _reflns_number_observed 2919 _reflns_observed_criterion >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXTL PLUS 5' _computing_structure_refinement 'SHELXTL PLUS 5' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement on F^2^ for ALL reflections except for 56 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^)+(0.0757P)^2^+0.0167P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _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 0.95(131) _refine_ls_number_reflns 4186 _refine_ls_number_parameters 257 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.1084 _refine_ls_R_factor_obs 0.0513 _refine_ls_wR_factor_all 0.1535 _refine_ls_wR_factor_obs 0.1184 _refine_ls_goodness_of_fit_all 1.022 _refine_ls_goodness_of_fit_obs 1.073 _refine_ls_restrained_S_all 1.147 _refine_ls_restrained_S_obs 1.073 _refine_ls_shift/esd_max 0.008 _refine_ls_shift/esd_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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group O1 O 0.23362(5) -0.4794(2) -0.4287(3) 0.0445(4) Uani 1 d . . O2 O 0.30490(5) -0.6016(2) -0.4197(2) 0.0413(3) Uani 1 d . . N1 N 0.35370(5) -0.1137(2) -0.1393(2) 0.0300(3) Uani 1 d . . N2 N 0.33632(5) 0.1929(2) 0.0036(2) 0.0276(3) Uani 1 d . . N3 N 0.27628(5) -0.4671(2) -0.3862(2) 0.0305(3) Uani 1 d . . C1 C 0.32234(5) 0.0359(2) -0.1001(2) 0.0247(2) Uani 1 d . . C2 C 0.27428(5) 0.0313(2) -0.1606(2) 0.0272(3) Uani 1 d . . C3 C 0.25869(5) -0.1325(2) -0.2559(2) 0.0277(3) Uani 1 d . . C4 C 0.29140(5) -0.2864(2) -0.2947(2) 0.0259(3) Uani 1 d . . C5 C 0.33803(6) -0.2701(3) -0.2359(2) 0.0294(3) Uani 1 d . . C6 C 0.38047(5) 0.2158(2) 0.1083(2) 0.0217(2) Uani 1 d . . C7 C 0.38543(6) 0.0448(2) 0.2489(2) 0.0278(3) Uani 1 d . . C8 C 0.42986(6) 0.0812(2) 0.3646(2) 0.0289(3) Uani 1 d . . C9 C 0.47379(6) 0.0865(3) 0.2424(3) 0.0317(3) Uani 1 d . . C10 C 0.46890(5) 0.2576(2) 0.1043(2) 0.0282(3) Uani 1 d . . C11 C 0.46432(6) 0.4612(3) 0.2038(3) 0.0314(3) Uani 1 d . . C12 C 0.42023(6) 0.4561(2) 0.3249(2) 0.0274(3) Uani 1 d . . C13 C 0.37605(5) 0.4202(2) 0.2077(2) 0.0258(3) Uani 1 d . . C14 C 0.42466(5) 0.2225(2) -0.0133(2) 0.0264(3) Uani 1 d . . C15 C 0.42498(6) 0.2846(3) 0.4644(2) 0.0307(3) Uani 1 d . . H2N H 0.3155(8) 0.2757(30) 0.0244(36) 0.030(5) Uiso 1 d . . H2 H 0.2523(10) 0.1406(33) -0.1260(43) 0.041(6) Uiso 1 d . . H3 H 0.2272(7) -0.1457(31) -0.2877(34) 0.024(5) Uiso 1 d . . H5 H 0.3588(7) -0.3732(34) -0.2665(32) 0.026(5) Uiso 1 d . . H7A H 0.3869(8) -0.0869(38) 0.1806(37) 0.032(6) Uiso 1 d . . H7B H 0.3561(12) 0.0317(48) 0.3147(59) 0.073(10) Uiso 1 d . . H8 H 0.4336(8) -0.0298(33) 0.4448(37) 0.030(5) Uiso 1 d . . H9A H 0.4754(8) -0.0471(42) 0.1847(48) 0.044(7) Uiso 1 d . . H9B H 0.5020(9) 0.1203(39) 0.3162(43) 0.037(6) Uiso 1 d . . H10A H 0.4989(9) 0.2626(35) 0.0286(41) 0.038(6) Uiso 1 d . . H11A H 0.4599(8) 0.5755(41) 0.1130(45) 0.042(7) Uiso 1 d . . H11B H 0.4938(10) 0.4867(46) 0.2780(42) 0.039(6) Uiso 1 d . . H12 H 0.4168(7) 0.5823(36) 0.3804(38) 0.032(5) Uiso 1 d . . H13A H 0.3730(9) 0.5233(38) 0.1201(42) 0.043(7) Uiso 1 d . . H13B H 0.3482(7) 0.4125(34) 0.2832(31) 0.024(5) Uiso 1 d . . H14A H 0.4282(8) 0.0944(39) -0.0864(40) 0.038(6) Uiso 1 d . . H14B H 0.4203(8) 0.3218(41) -0.1019(43) 0.043(7) Uiso 1 d . . H15A H 0.4535(8) 0.3139(36) 0.5388(38) 0.036(6) Uiso 1 d . . H15B H 0.3954(8) 0.2829(34) 0.5468(38) 0.038(6) Uiso 1 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 0.0377(6) 0.0379(7) 0.0578(10) -0.0009(7) -0.0158(7) -0.0143(5) O2 0.0442(7) 0.0360(6) 0.0436(8) -0.0142(6) 0.0060(6) -0.0067(5) N1 0.0249(5) 0.0304(6) 0.0347(7) -0.0109(6) -0.0070(5) 0.0036(4) N2 0.0241(5) 0.0282(6) 0.0305(6) -0.0088(5) -0.0074(5) 0.0067(4) N3 0.0357(6) 0.0307(6) 0.0250(6) -0.0004(5) -0.0005(5) -0.0114(5) C1 0.0229(5) 0.0269(6) 0.0243(6) -0.0029(5) -0.0046(5) 0.0009(5) C2 0.0227(5) 0.0306(6) 0.0281(7) -0.0005(6) -0.0040(5) 0.0030(5) C3 0.0234(6) 0.0336(7) 0.0260(6) 0.0012(6) -0.0050(5) -0.0021(5) C4 0.0273(6) 0.0281(6) 0.0223(6) -0.0014(5) -0.0015(5) -0.0050(5) C5 0.0256(6) 0.0313(7) 0.0313(7) -0.0088(6) -0.0027(5) 0.0012(5) C6 0.0225(5) 0.0208(5) 0.0219(5) -0.0025(5) -0.0031(5) 0.0028(4) C7 0.0272(6) 0.0245(6) 0.0315(7) 0.0032(6) -0.0051(6) -0.0036(5) C8 0.0291(7) 0.0282(6) 0.0295(7) 0.0044(6) -0.0070(6) -0.0008(5) C9 0.0253(6) 0.0313(7) 0.0383(8) -0.0016(7) -0.0067(6) 0.0039(5) C10 0.0231(6) 0.0316(7) 0.0301(7) -0.0033(6) 0.0032(6) -0.0014(5) C11 0.0317(7) 0.0272(7) 0.0351(8) -0.0032(7) -0.0003(6) -0.0069(5) C12 0.0295(6) 0.0252(6) 0.0274(7) -0.0067(6) -0.0022(5) -0.0014(5) C13 0.0284(6) 0.0231(5) 0.0258(6) -0.0049(5) -0.0022(5) 0.0049(5) C14 0.0259(6) 0.0293(6) 0.0238(6) -0.0038(5) 0.0008(5) 0.0019(5) C15 0.0305(7) 0.0389(8) 0.0226(6) -0.0013(6) -0.0048(5) -0.0032(6) _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 N3 1.244(2) . ? O2 N3 1.223(2) . ? N1 C5 1.328(2) . ? N1 C1 1.354(2) . ? N2 C1 1.346(2) . ? N2 C6 1.472(2) . ? N3 C4 1.433(2) . ? C1 C2 1.426(2) . ? C2 C3 1.362(2) . ? C3 C4 1.399(2) . ? C4 C5 1.387(2) . ? C6 C14 1.536(2) . ? C6 C13 1.538(2) . ? C6 C7 1.539(2) . ? C7 C8 1.534(2) . ? C8 C9 1.532(3) . ? C8 C15 1.535(2) . ? C9 C10 1.527(3) . ? C10 C11 1.535(2) . ? C10 C14 1.537(2) . ? C11 C12 1.532(2) . ? C12 C13 1.535(2) . ? C12 C15 1.535(2) . ? 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 N1 C1 117.54(13) . . ? C1 N2 C6 128.68(12) . . ? O2 N3 O1 122.5(2) . . ? O2 N3 C4 120.07(14) . . ? O1 N3 C4 117.4(2) . . ? N2 C1 N1 119.35(13) . . ? N2 C1 C2 118.20(13) . . ? N1 C1 C2 122.43(14) . . ? C3 C2 C1 119.04(14) . . ? C2 C3 C4 117.88(13) . . ? C5 C4 C3 120.19(14) . . ? C5 C4 N3 119.57(14) . . ? C3 C4 N3 120.15(13) . . ? N1 C5 C4 122.89(15) . . ? N2 C6 C14 112.29(12) . . ? N2 C6 C13 105.81(10) . . ? C14 C6 C13 108.70(12) . . ? N2 C6 C7 110.91(12) . . ? C14 C6 C7 110.06(12) . . ? C13 C6 C7 108.92(13) . . ? C8 C7 C6 109.67(12) . . ? C9 C8 C7 109.44(15) . . ? C9 C8 C15 109.63(14) . . ? C7 C8 C15 109.34(13) . . ? C10 C9 C8 109.78(13) . . ? C9 C10 C11 109.38(15) . . ? C9 C10 C14 109.90(13) . . ? C11 C10 C14 109.55(13) . . ? C12 C11 C10 109.22(12) . . ? C11 C12 C13 109.26(14) . . ? C11 C12 C15 109.81(14) . . ? C13 C12 C15 109.69(13) . . ? C12 C13 C6 109.83(11) . . ? C6 C14 C10 109.24(12) . . ? C12 C15 C8 109.04(13) . . ? _refine_diff_density_max 0.300 _refine_diff_density_min -0.243 _refine_diff_density_rms 0.048