Supplementary Material for Organic & Biomolecular Chemistry This journal is © The Royal Society of Chemistry 2003 Supplementary data data_global _journal_coden_Cambridge 177 loop_ _publ_author_name 'Steven Ley' 'Ian R. Baxendale' 'Jason Siu' _publ_contact_author_name 'Prof Steven Ley' _publ_contact_author_address ; Department of Chemistry The University of Cambridge Lensfield Road, Cambridge CB2 1EW UNITED KINGDOM ; _publ_contact_author_email SVL1000@CAM.AC.UK _publ_requested_journal 'Organic & Biomolecular Chemistry' _publ_section_title ; Microwave assisted Leimgruber-Batcho reaction for the preparation of indoles, azaindoles and pyrroylquinolines. ; data_sl0312 _database_code_depnum_ccdc_archive 'CCDC 217042' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C11 H11 N3 O2' _chemical_formula_sum 'C11 H11 N3 O2' _chemical_formula_weight 217.23 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 Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.2055(6) _cell_length_b 7.8564(7) _cell_length_c 9.9993(8) _cell_angle_alpha 101.554(6) _cell_angle_beta 92.508(6) _cell_angle_gamma 103.229(3) _cell_volume 537.48(8) _cell_formula_units_Z 2 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 6384 _cell_measurement_theta_min 1.02 _cell_measurement_theta_max 25.03 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.342 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 228 _exptl_absorpt_coefficient_mu 0.096 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.907 _exptl_absorpt_correction_T_max 0.994 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 180(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_measurement_method 'Thin slice \w and \f scans' _diffrn_reflns_number 5051 _diffrn_reflns_av_R_equivalents 0.0728 _diffrn_reflns_av_sigmaI/netI 0.0751 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 4.18 _diffrn_reflns_theta_max 25.02 _reflns_number_total 1867 _reflns_number_gt 1241 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V. 1998)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction ; HKL Denzo and Scalepack (Otwinowski & Minor 1997) ; _computing_structure_solution 'SIR-92 (Altomare et al. 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick 1997)' _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^)+(0.1529P)^2^+0.0735P] 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 1867 _refine_ls_number_parameters 147 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1164 _refine_ls_R_factor_gt 0.0787 _refine_ls_wR_factor_ref 0.2499 _refine_ls_wR_factor_gt 0.2195 _refine_ls_goodness_of_fit_ref 1.066 _refine_ls_restrained_S_all 1.066 _refine_ls_shift/su_max 0.380 _refine_ls_shift/su_mean 0.014 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 0.2754(4) 0.7115(3) 0.8951(3) 0.0587(9) Uani 1 1 d . . . O2 O 0.1962(4) 0.6083(3) 1.0725(2) 0.0509(8) Uani 1 1 d . . . N1 N 0.5797(5) 0.2837(4) 0.4672(3) 0.0528(9) Uani 1 1 d . . . N2 N 0.2535(4) 0.5897(4) 0.9580(3) 0.0360(8) Uani 1 1 d . . . N3 N 0.1262(4) 0.1055(4) 1.2664(3) 0.0400(8) Uani 1 1 d . . . C1 C 0.4245(5) 0.2768(4) 0.6960(3) 0.0339(8) Uani 1 1 d . . . C2 C 0.3983(5) 0.1222(5) 0.7510(3) 0.0368(9) Uani 1 1 d . . . H2 H 0.4319 0.0184 0.7023 0.044 Uiso 1 1 calc R . . C3 C 0.3249(5) 0.1216(4) 0.8738(3) 0.0349(8) Uani 1 1 d . . . H3 H 0.3079 0.0151 0.9080 0.042 Uiso 1 1 calc R . . C4 C 0.2718(4) 0.2716(4) 0.9546(3) 0.0308(8) Uani 1 1 d . . . C5 C 0.2970(4) 0.4230(4) 0.8926(3) 0.0320(8) Uani 1 1 d . . . C6 C 0.3732(4) 0.4257(4) 0.7669(3) 0.0341(8) Uani 1 1 d . . . H6 H 0.3897 0.5302 0.7303 0.041 Uiso 1 1 calc R . . C7 C 0.5106(5) 0.2818(4) 0.5695(3) 0.0388(9) Uani 1 1 d . . . C8 C 0.2020(5) 0.2613(4) 1.0854(3) 0.0355(8) Uani 1 1 d . . . H8 H 0.1630 0.3617 1.1348 0.043 Uiso 1 1 calc R . . C9 C 0.1879(4) 0.1159(5) 1.1438(3) 0.0353(8) Uani 1 1 d . . . H9 H 0.2248 0.0150 1.0932 0.042 Uiso 1 1 calc R . . C10 C 0.0666(6) 0.2540(5) 1.3516(4) 0.0494(10) Uani 1 1 d . . . H10A H -0.0362 0.2842 1.3006 0.074 Uiso 1 1 calc R . . H10B H 0.1759 0.3584 1.3762 0.074 Uiso 1 1 calc R . . H10C H 0.0202 0.2190 1.4352 0.074 Uiso 1 1 calc R . . C11 C 0.1208(5) -0.0520(5) 1.3221(4) 0.0434(9) Uani 1 1 d . . . H11A H 0.1634 -0.1416 1.2556 0.065 Uiso 1 1 calc R . . H11B H -0.0104 -0.1021 1.3412 0.065 Uiso 1 1 calc R . . H11C H 0.2058 -0.0189 1.4073 0.065 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 O1 0.090(2) 0.0419(16) 0.0615(18) 0.0299(13) 0.0240(14) 0.0301(14) O2 0.0770(19) 0.0420(15) 0.0386(15) 0.0102(11) 0.0150(13) 0.0216(13) N1 0.075(2) 0.0453(19) 0.0439(19) 0.0163(14) 0.0216(16) 0.0184(16) N2 0.0451(18) 0.0321(16) 0.0340(16) 0.0118(12) 0.0040(12) 0.0117(12) N3 0.0485(18) 0.0390(17) 0.0343(16) 0.0134(12) 0.0099(12) 0.0087(13) C1 0.0412(19) 0.0307(18) 0.0304(17) 0.0103(13) 0.0040(13) 0.0063(14) C2 0.043(2) 0.0298(18) 0.0366(19) 0.0051(14) 0.0056(14) 0.0089(15) C3 0.044(2) 0.0264(17) 0.0368(19) 0.0129(14) 0.0057(14) 0.0081(14) C4 0.0323(17) 0.0282(18) 0.0306(18) 0.0067(13) 0.0001(13) 0.0048(13) C5 0.0371(18) 0.0282(17) 0.0317(17) 0.0074(13) 0.0023(13) 0.0093(13) C6 0.0394(19) 0.0305(18) 0.0337(18) 0.0137(14) 0.0011(14) 0.0057(14) C7 0.053(2) 0.0296(19) 0.035(2) 0.0102(14) 0.0057(15) 0.0103(15) C8 0.039(2) 0.0327(19) 0.0352(19) 0.0082(14) 0.0061(14) 0.0093(15) C9 0.0369(19) 0.0379(19) 0.0318(18) 0.0126(14) 0.0061(14) 0.0058(15) C10 0.069(3) 0.048(2) 0.038(2) 0.0148(16) 0.0163(17) 0.0210(19) C11 0.055(2) 0.042(2) 0.039(2) 0.0196(16) 0.0105(16) 0.0111(17) _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 N2 1.231(4) . ? O2 N2 1.227(3) . ? N1 C7 1.158(4) . ? N2 C5 1.450(4) . ? N3 C9 1.334(4) . ? N3 C11 1.449(4) . ? N3 C10 1.461(5) . ? C1 C6 1.377(4) . ? C1 C2 1.410(5) . ? C1 C7 1.436(5) . ? C2 C3 1.358(5) . ? C2 H2 0.9500 . ? C3 C4 1.429(4) . ? C3 H3 0.9500 . ? C4 C5 1.427(4) . ? C4 C8 1.433(4) . ? C5 C6 1.396(4) . ? C6 H6 0.9500 . ? C8 C9 1.369(5) . ? C8 H8 0.9500 . ? C9 H9 0.9500 . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? 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 O2 N2 O1 121.1(3) . . ? O2 N2 C5 120.8(3) . . ? O1 N2 C5 118.1(3) . . ? C9 N3 C11 121.2(3) . . ? C9 N3 C10 121.5(3) . . ? C11 N3 C10 117.3(3) . . ? C6 C1 C2 119.5(3) . . ? C6 C1 C7 120.1(3) . . ? C2 C1 C7 120.4(3) . . ? C3 C2 C1 120.0(3) . . ? C3 C2 H2 120.0 . . ? C1 C2 H2 120.0 . . ? C2 C3 C4 123.8(3) . . ? C2 C3 H3 118.1 . . ? C4 C3 H3 118.1 . . ? C5 C4 C3 113.9(3) . . ? C5 C4 C8 126.1(3) . . ? C3 C4 C8 120.1(3) . . ? C6 C5 C4 122.8(3) . . ? C6 C5 N2 114.3(3) . . ? C4 C5 N2 122.8(3) . . ? C1 C6 C5 120.0(3) . . ? C1 C6 H6 120.0 . . ? C5 C6 H6 120.0 . . ? N1 C7 C1 179.2(3) . . ? C9 C8 C4 124.1(3) . . ? C9 C8 H8 117.9 . . ? C4 C8 H8 117.9 . . ? N3 C9 C8 124.8(3) . . ? N3 C9 H9 117.6 . . ? C8 C9 H9 117.6 . . ? N3 C10 H10A 109.5 . . ? N3 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? N3 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? N3 C11 H11A 109.5 . . ? N3 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? N3 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? 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 C6 C1 C2 C3 -0.7(5) . . . . ? C7 C1 C2 C3 177.0(3) . . . . ? C1 C2 C3 C4 -0.5(5) . . . . ? C2 C3 C4 C5 1.9(5) . . . . ? C2 C3 C4 C8 -177.7(3) . . . . ? C3 C4 C5 C6 -2.2(4) . . . . ? C8 C4 C5 C6 177.3(3) . . . . ? C3 C4 C5 N2 -179.4(3) . . . . ? C8 C4 C5 N2 0.1(5) . . . . ? O2 N2 C5 C6 -175.8(3) . . . . ? O1 N2 C5 C6 4.4(4) . . . . ? O2 N2 C5 C4 1.7(5) . . . . ? O1 N2 C5 C4 -178.2(3) . . . . ? C2 C1 C6 C5 0.4(5) . . . . ? C7 C1 C6 C5 -177.3(3) . . . . ? C4 C5 C6 C1 1.2(5) . . . . ? N2 C5 C6 C1 178.6(3) . . . . ? C6 C1 C7 N1 -169(28) . . . . ? C2 C1 C7 N1 13(28) . . . . ? C5 C4 C8 C9 -177.0(3) . . . . ? C3 C4 C8 C9 2.5(5) . . . . ? C11 N3 C9 C8 -178.2(3) . . . . ? C10 N3 C9 C8 -0.1(5) . . . . ? C4 C8 C9 N3 178.8(3) . . . . ? _diffrn_measured_fraction_theta_max 0.981 _diffrn_reflns_theta_full 25.02 _diffrn_measured_fraction_theta_full 0.981 _refine_diff_density_max 0.381 _refine_diff_density_min -0.347 _refine_diff_density_rms 0.091 data_sl0327 _database_code_depnum_ccdc_archive 'CCDC 217043' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C13 H13 N3 O2' _chemical_formula_sum 'C13 H13 N3 O2' _chemical_formula_weight 243.26 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 Monoclinic _symmetry_space_group_name_H-M P2(1)/c 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 7.3056(4) _cell_length_b 13.9174(9) _cell_length_c 12.4289(8) _cell_angle_alpha 90.00 _cell_angle_beta 106.530(3) _cell_angle_gamma 90.00 _cell_volume 1211.48(13) _cell_formula_units_Z 4 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 6583 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 27.48 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.334 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 512 _exptl_absorpt_coefficient_mu 0.093 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.439 _exptl_absorpt_correction_T_max 1.160 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _exptl_special_details ; Xtals poor (mostly split): this is the best of two datasets. High R(merge) reflected in high final R values (JED). ; _diffrn_ambient_temperature 180(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_measurement_method 'Thin slice \w and \f scans' _diffrn_reflns_number 6595 _diffrn_reflns_av_R_equivalents 0.1078 _diffrn_reflns_av_sigmaI/netI 0.1055 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 3.72 _diffrn_reflns_theta_max 27.46 _reflns_number_total 2688 _reflns_number_gt 1485 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V. 1998)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction ; HKL Denzo and Scalepack (Otwinowski & Minor 1997) ; _computing_structure_solution 'SIR-92 (Altomare et al. 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick 1997)' _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^)+(0.0675P)^2^+1.3416P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.014(5) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2688 _refine_ls_number_parameters 166 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1502 _refine_ls_R_factor_gt 0.0874 _refine_ls_wR_factor_ref 0.2397 _refine_ls_wR_factor_gt 0.2058 _refine_ls_goodness_of_fit_ref 1.073 _refine_ls_restrained_S_all 1.073 _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 N1 N 0.8076(5) 0.0339(2) 0.2382(2) 0.0434(8) Uani 1 1 d . . . O1 O 0.6664(5) 0.0369(3) 0.2711(2) 0.0755(11) Uani 1 1 d . . . O2 O 0.9676(5) 0.0203(2) 0.3013(2) 0.0679(10) Uani 1 1 d . . . N2 N 0.8595(5) 0.2128(2) 0.1645(2) 0.0438(8) Uani 1 1 d . . . N3 N 0.6410(5) -0.2936(2) 0.0435(3) 0.0597(10) Uani 1 1 d . . . C1 C 0.7867(5) 0.0472(2) 0.1177(3) 0.0376(8) Uani 1 1 d . . . C2 C 0.8200(5) 0.1413(2) 0.0860(3) 0.0369(8) Uani 1 1 d . . . C3 C 0.8901(6) 0.2996(3) 0.1295(3) 0.0483(10) Uani 1 1 d . . . H3 H 0.9178 0.3498 0.1834 0.058 Uiso 1 1 calc R . . C4 C 0.8846(6) 0.3227(3) 0.0201(3) 0.0489(10) Uani 1 1 d . . . H4 H 0.9078 0.3866 0.0007 0.059 Uiso 1 1 calc R . . C5 C 0.8449(6) 0.2514(3) -0.0598(3) 0.0479(10) Uani 1 1 d . . . H5 H 0.8414 0.2653 -0.1352 0.057 Uiso 1 1 calc R . . C6 C 0.8097(5) 0.1581(3) -0.0288(3) 0.0387(8) Uani 1 1 d . . . C7 C 0.7667(6) 0.0785(3) -0.1035(3) 0.0484(10) Uani 1 1 d . . . H7 H 0.7592 0.0881 -0.1804 0.058 Uiso 1 1 calc R . . C8 C 0.7362(6) -0.0102(3) -0.0684(3) 0.0461(9) Uani 1 1 d . . . H8 H 0.7081 -0.0611 -0.1216 0.055 Uiso 1 1 calc R . . C9 C 0.7445(5) -0.0311(2) 0.0466(3) 0.0385(8) Uani 1 1 d . . . C10 C 0.7125(5) -0.1264(3) 0.0834(3) 0.0429(9) Uani 1 1 d . . . H10 H 0.7193 -0.1351 0.1603 0.051 Uiso 1 1 calc R . . C11 C 0.6736(6) -0.2041(3) 0.0153(3) 0.0483(10) Uani 1 1 d . . . H11 H 0.6689 -0.1938 -0.0609 0.058 Uiso 1 1 calc R . . C12 C 0.6520(7) -0.3187(3) 0.1583(4) 0.0694(13) Uani 1 1 d . . . H12A H 0.5659 -0.2772 0.1852 0.104 Uiso 1 1 calc R . . H12B H 0.7832 -0.3098 0.2058 0.104 Uiso 1 1 calc R . . H12C H 0.6145 -0.3860 0.1616 0.104 Uiso 1 1 calc R . . C13 C 0.6155(8) -0.3726(3) -0.0367(4) 0.0763(15) Uani 1 1 d . . . H13A H 0.6011 -0.3468 -0.1120 0.114 Uiso 1 1 calc R . . H13B H 0.5010 -0.4092 -0.0365 0.114 Uiso 1 1 calc R . . H13C H 0.7273 -0.4149 -0.0154 0.114 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 N1 0.060(2) 0.0342(17) 0.0326(15) -0.0010(13) 0.0077(16) -0.0018(15) O1 0.074(2) 0.113(3) 0.0422(16) -0.0080(17) 0.0206(16) -0.017(2) O2 0.081(2) 0.066(2) 0.0403(15) 0.0054(14) -0.0091(15) 0.0148(16) N2 0.0557(19) 0.0343(16) 0.0357(16) -0.0040(13) 0.0035(14) -0.0008(14) N3 0.074(2) 0.0336(19) 0.067(2) -0.0102(17) 0.0126(19) -0.0079(17) C1 0.044(2) 0.0361(19) 0.0279(16) -0.0011(14) 0.0025(15) 0.0050(16) C2 0.0388(19) 0.0326(19) 0.0341(18) -0.0035(14) 0.0021(14) 0.0011(15) C3 0.057(2) 0.036(2) 0.044(2) -0.0039(17) 0.0016(18) -0.0018(17) C4 0.059(2) 0.034(2) 0.051(2) 0.0071(17) 0.0105(19) 0.0029(18) C5 0.054(2) 0.049(2) 0.039(2) 0.0073(17) 0.0114(17) 0.0009(19) C6 0.0400(19) 0.037(2) 0.0358(19) -0.0006(15) 0.0058(15) -0.0004(15) C7 0.060(2) 0.053(2) 0.0282(18) -0.0036(17) 0.0067(17) 0.0009(19) C8 0.056(2) 0.041(2) 0.0385(19) -0.0104(17) 0.0078(17) -0.0004(18) C9 0.042(2) 0.0322(19) 0.0367(18) -0.0048(15) 0.0028(15) 0.0020(15) C10 0.048(2) 0.036(2) 0.041(2) -0.0032(16) 0.0072(16) 0.0029(16) C11 0.053(2) 0.038(2) 0.052(2) -0.0073(18) 0.0117(19) -0.0035(17) C12 0.071(3) 0.047(3) 0.077(3) 0.010(2) 0.000(2) -0.008(2) C13 0.091(4) 0.036(2) 0.099(4) -0.025(2) 0.023(3) -0.005(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 N1 O1 1.213(4) . ? N1 O2 1.222(4) . ? N1 C1 1.474(4) . ? N2 C3 1.324(5) . ? N2 C2 1.365(4) . ? N3 C11 1.333(5) . ? N3 C12 1.449(6) . ? N3 C13 1.460(5) . ? C1 C9 1.381(5) . ? C1 C2 1.408(5) . ? C2 C6 1.427(5) . ? C3 C4 1.386(5) . ? C3 H3 0.9500 . ? C4 C5 1.376(5) . ? C4 H4 0.9500 . ? C5 C6 1.399(5) . ? C5 H5 0.9500 . ? C6 C7 1.422(5) . ? C7 C8 1.349(5) . ? C7 H7 0.9500 . ? C8 C9 1.444(5) . ? C8 H8 0.9500 . ? C9 C10 1.444(5) . ? C10 C11 1.352(5) . ? C10 H10 0.9500 . ? C11 H11 0.9500 . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? 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 O1 N1 O2 122.6(3) . . ? O1 N1 C1 119.0(3) . . ? O2 N1 C1 118.3(3) . . ? C3 N2 C2 116.8(3) . . ? C11 N3 C12 121.3(3) . . ? C11 N3 C13 121.5(4) . . ? C12 N3 C13 116.8(4) . . ? C9 C1 C2 125.4(3) . . ? C9 C1 N1 119.4(3) . . ? C2 C1 N1 115.2(3) . . ? N2 C2 C1 119.8(3) . . ? N2 C2 C6 122.4(3) . . ? C1 C2 C6 117.9(3) . . ? N2 C3 C4 125.0(3) . . ? N2 C3 H3 117.5 . . ? C4 C3 H3 117.5 . . ? C5 C4 C3 118.8(4) . . ? C5 C4 H4 120.6 . . ? C3 C4 H4 120.6 . . ? C4 C5 C6 119.2(3) . . ? C4 C5 H5 120.4 . . ? C6 C5 H5 120.4 . . ? C5 C6 C7 124.5(3) . . ? C5 C6 C2 117.7(3) . . ? C7 C6 C2 117.7(3) . . ? C8 C7 C6 121.8(3) . . ? C8 C7 H7 119.1 . . ? C6 C7 H7 119.1 . . ? C7 C8 C9 122.7(3) . . ? C7 C8 H8 118.7 . . ? C9 C8 H8 118.7 . . ? C1 C9 C8 114.5(3) . . ? C1 C9 C10 123.3(3) . . ? C8 C9 C10 122.2(3) . . ? C11 C10 C9 124.1(3) . . ? C11 C10 H10 117.9 . . ? C9 C10 H10 117.9 . . ? N3 C11 C10 127.2(4) . . ? N3 C11 H11 116.4 . . ? C10 C11 H11 116.4 . . ? N3 C12 H12A 109.5 . . ? N3 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? N3 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? N3 C13 H13A 109.5 . . ? N3 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? N3 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? 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 O1 N1 C1 C9 -86.1(4) . . . . ? O2 N1 C1 C9 94.1(4) . . . . ? O1 N1 C1 C2 96.2(4) . . . . ? O2 N1 C1 C2 -83.6(4) . . . . ? C3 N2 C2 C1 179.8(3) . . . . ? C3 N2 C2 C6 -0.6(5) . . . . ? C9 C1 C2 N2 179.6(3) . . . . ? N1 C1 C2 N2 -2.9(5) . . . . ? C9 C1 C2 C6 0.0(5) . . . . ? N1 C1 C2 C6 177.5(3) . . . . ? C2 N2 C3 C4 0.1(6) . . . . ? N2 C3 C4 C5 -0.1(6) . . . . ? C3 C4 C5 C6 0.5(6) . . . . ? C4 C5 C6 C7 179.8(4) . . . . ? C4 C5 C6 C2 -1.0(5) . . . . ? N2 C2 C6 C5 1.1(5) . . . . ? C1 C2 C6 C5 -179.3(3) . . . . ? N2 C2 C6 C7 -179.7(3) . . . . ? C1 C2 C6 C7 -0.1(5) . . . . ? C5 C6 C7 C8 179.2(4) . . . . ? C2 C6 C7 C8 0.0(6) . . . . ? C6 C7 C8 C9 0.1(6) . . . . ? C2 C1 C9 C8 0.1(5) . . . . ? N1 C1 C9 C8 -177.3(3) . . . . ? C2 C1 C9 C10 179.6(3) . . . . ? N1 C1 C9 C10 2.2(5) . . . . ? C7 C8 C9 C1 -0.2(5) . . . . ? C7 C8 C9 C10 -179.7(4) . . . . ? C1 C9 C10 C11 -179.1(4) . . . . ? C8 C9 C10 C11 0.4(6) . . . . ? C12 N3 C11 C10 -2.5(7) . . . . ? C13 N3 C11 C10 -175.1(4) . . . . ? C9 C10 C11 N3 -179.3(4) . . . . ? _diffrn_measured_fraction_theta_max 0.968 _diffrn_reflns_theta_full 27.46 _diffrn_measured_fraction_theta_full 0.968 _refine_diff_density_max 0.245 _refine_diff_density_min -0.241 _refine_diff_density_rms 0.067 data_sl0324 _database_code_depnum_ccdc_archive 'CCDC 217044' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C13 H18 N4 O2' _chemical_formula_sum 'C13 H18 N4 O2' _chemical_formula_weight 262.31 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 Monoclinic _symmetry_space_group_name_H-M P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 11.8517(4) _cell_length_b 7.4800(2) _cell_length_c 15.7266(6) _cell_angle_alpha 90.00 _cell_angle_beta 96.8390(10) _cell_angle_gamma 90.00 _cell_volume 1384.25(8) _cell_formula_units_Z 4 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 5931 _cell_measurement_theta_min 1.0 _cell_measurement_theta_max 27.48 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.46 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.23 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.259 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 560 _exptl_absorpt_coefficient_mu 0.088 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.877 _exptl_absorpt_correction_T_max 0.986 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 180(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_measurement_method 'Thin slice \w and \f scans' _diffrn_reflns_number 8014 _diffrn_reflns_av_R_equivalents 0.0377 _diffrn_reflns_av_sigmaI/netI 0.0381 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 3.56 _diffrn_reflns_theta_max 27.60 _reflns_number_total 3117 _reflns_number_gt 2473 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V. 1998)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction ; HKL Denzo and Scalepack (Otwinowski & Minor 1997) ; _computing_structure_solution 'SIR-92 (Altomare et al. 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick 1997)' _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^)+(0.0638P)^2^+0.5996P] 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 3117 _refine_ls_number_parameters 176 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0765 _refine_ls_R_factor_gt 0.0606 _refine_ls_wR_factor_ref 0.1589 _refine_ls_wR_factor_gt 0.1483 _refine_ls_goodness_of_fit_ref 1.064 _refine_ls_restrained_S_all 1.064 _refine_ls_shift/su_max 0.003 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.40278(14) 0.1574(4) 0.28932(12) 0.1183(10) Uani 1 1 d . . . O2 O 0.43968(13) 0.0528(3) 0.17032(11) 0.0782(6) Uani 1 1 d . . . N1 N 0.47088(13) 0.0957(3) 0.24496(10) 0.0539(4) Uani 1 1 d . . . N2 N 1.09814(13) 0.1729(2) 0.44828(10) 0.0475(4) Uani 1 1 d . . . N3 N 0.57709(13) 0.3013(2) 0.57260(10) 0.0496(4) Uani 1 1 d . . . N4 N 0.75033(12) 0.12577(19) 0.38094(9) 0.0375(3) Uani 1 1 d . . . C1 C 0.58872(15) 0.0793(2) 0.27699(11) 0.0398(4) Uani 1 1 d . . . C2 C 0.65997(15) 0.0098(2) 0.22029(11) 0.0416(4) Uani 1 1 d . . . H2 H 0.6285 -0.0324 0.1656 0.050 Uiso 1 1 calc R . . C3 C 0.77368(15) 0.0026(2) 0.24316(12) 0.0428(4) Uani 1 1 d . . . H3 H 0.8223 -0.0453 0.2051 0.051 Uiso 1 1 calc R . . C4 C 0.81892(15) 0.0675(2) 0.32455(11) 0.0373(4) Uani 1 1 d . . . C5 C 0.63630(14) 0.1337(2) 0.36074(10) 0.0359(4) Uani 1 1 d . . . C6 C 0.57237(15) 0.1949(2) 0.42766(11) 0.0397(4) Uani 1 1 d . . . H6 H 0.4917 0.1970 0.4180 0.048 Uiso 1 1 calc R . . C7 C 0.62603(15) 0.2494(2) 0.50429(11) 0.0421(4) Uani 1 1 d . . . H7 H 0.7067 0.2510 0.5100 0.050 Uiso 1 1 calc R . . C8 C 0.45483(17) 0.2967(3) 0.57155(13) 0.0532(5) Uani 1 1 d . . . H8A H 0.4265 0.1778 0.5537 0.080 Uiso 1 1 calc R . . H8B H 0.4201 0.3864 0.5312 0.080 Uiso 1 1 calc R . . H8C H 0.4351 0.3227 0.6290 0.080 Uiso 1 1 calc R . . C9 C 0.6439(2) 0.3545(4) 0.65179(14) 0.0692(7) Uani 1 1 d . . . H9A H 0.7245 0.3576 0.6435 0.104 Uiso 1 1 calc R . . H9B H 0.6324 0.2684 0.6969 0.104 Uiso 1 1 calc R . . H9C H 0.6198 0.4736 0.6685 0.104 Uiso 1 1 calc R . . C10 C 0.93974(15) 0.0741(2) 0.34716(11) 0.0418(4) Uani 1 1 d . . . H10 H 0.9877 0.0207 0.3100 0.050 Uiso 1 1 calc R . . C11 C 0.98746(15) 0.1545(2) 0.42014(11) 0.0411(4) Uani 1 1 d . . . H11 H 0.9360 0.2040 0.4557 0.049 Uiso 1 1 calc R . . C12 C 1.18480(17) 0.1090(4) 0.39857(15) 0.0694(7) Uani 1 1 d . . . H12A H 1.1604 -0.0044 0.3711 0.104 Uiso 1 1 calc R . . H12B H 1.2558 0.0907 0.4363 0.104 Uiso 1 1 calc R . . H12C H 1.1970 0.1974 0.3546 0.104 Uiso 1 1 calc R . . C13 C 1.13413(17) 0.2912(3) 0.51903(13) 0.0554(5) Uani 1 1 d . . . H13A H 1.0693 0.3179 0.5502 0.083 Uiso 1 1 calc R . . H13B H 1.1633 0.4025 0.4971 0.083 Uiso 1 1 calc R . . H13C H 1.1942 0.2334 0.5577 0.083 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 O1 0.0435(9) 0.246(3) 0.0637(11) -0.0543(15) -0.0018(8) 0.0187(13) O2 0.0545(9) 0.1155(15) 0.0603(10) -0.0306(10) -0.0106(7) 0.0025(9) N1 0.0414(9) 0.0724(12) 0.0467(9) -0.0112(8) 0.0004(7) -0.0064(8) N2 0.0382(8) 0.0648(11) 0.0389(8) 0.0058(7) 0.0023(6) 0.0061(7) N3 0.0474(9) 0.0607(10) 0.0407(8) -0.0063(7) 0.0054(7) 0.0057(7) N4 0.0390(7) 0.0372(8) 0.0360(7) 0.0045(6) 0.0035(6) 0.0036(6) C1 0.0401(9) 0.0370(9) 0.0417(9) 0.0013(7) 0.0026(7) -0.0056(7) C2 0.0510(10) 0.0346(9) 0.0383(9) -0.0038(7) 0.0013(7) -0.0040(7) C3 0.0493(10) 0.0351(9) 0.0446(9) -0.0048(7) 0.0088(8) 0.0037(7) C4 0.0436(9) 0.0309(8) 0.0374(8) 0.0041(7) 0.0044(7) 0.0039(7) C5 0.0396(9) 0.0313(8) 0.0365(8) 0.0037(7) 0.0038(7) -0.0022(6) C6 0.0393(9) 0.0388(9) 0.0414(9) 0.0032(7) 0.0064(7) 0.0004(7) C7 0.0421(9) 0.0433(10) 0.0410(9) 0.0019(8) 0.0055(7) 0.0047(8) C8 0.0545(12) 0.0535(12) 0.0547(11) -0.0004(9) 0.0190(9) 0.0035(9) C9 0.0691(14) 0.0926(18) 0.0449(11) -0.0164(12) 0.0023(10) 0.0036(13) C10 0.0406(9) 0.0443(10) 0.0411(9) 0.0040(8) 0.0069(7) 0.0104(7) C11 0.0392(9) 0.0447(10) 0.0398(9) 0.0082(7) 0.0060(7) 0.0062(7) C12 0.0400(11) 0.110(2) 0.0581(13) -0.0002(13) 0.0038(9) 0.0211(12) C13 0.0475(11) 0.0676(14) 0.0495(11) 0.0018(10) -0.0004(9) -0.0053(9) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 N1 1.219(2) . ? O2 N1 1.231(2) . ? N1 C1 1.432(2) . ? N2 C11 1.341(2) . ? N2 C12 1.444(3) . ? N2 C13 1.446(3) . ? N3 C7 1.338(2) . ? N3 C8 1.447(2) . ? N3 C9 1.450(3) . ? N4 C4 1.345(2) . ? N4 C5 1.352(2) . ? C1 C2 1.399(2) . ? C1 C5 1.429(2) . ? C2 C3 1.354(3) . ? C2 H2 0.9500 . ? C3 C4 1.413(2) . ? C3 H3 0.9500 . ? C4 C10 1.435(2) . ? C5 C6 1.443(2) . ? C6 C7 1.357(2) . ? C6 H6 0.9500 . ? C7 H7 0.9500 . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? C10 C11 1.358(3) . ? C10 H10 0.9500 . ? C11 H11 0.9500 . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? 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 O1 N1 O2 120.04(17) . . ? O1 N1 C1 121.05(16) . . ? O2 N1 C1 118.85(16) . . ? C11 N2 C12 121.23(17) . . ? C11 N2 C13 120.27(16) . . ? C12 N2 C13 117.09(17) . . ? C7 N3 C8 120.87(16) . . ? C7 N3 C9 121.67(17) . . ? C8 N3 C9 117.37(16) . . ? C4 N4 C5 121.66(15) . . ? C2 C1 C5 119.43(16) . . ? C2 C1 N1 116.43(16) . . ? C5 C1 N1 124.12(16) . . ? C3 C2 C1 120.18(17) . . ? C3 C2 H2 119.9 . . ? C1 C2 H2 119.9 . . ? C2 C3 C4 119.03(16) . . ? C2 C3 H3 120.5 . . ? C4 C3 H3 120.5 . . ? N4 C4 C3 120.96(16) . . ? N4 C4 C10 119.29(15) . . ? C3 C4 C10 119.75(15) . . ? N4 C5 C1 118.54(15) . . ? N4 C5 C6 116.07(15) . . ? C1 C5 C6 125.38(15) . . ? C7 C6 C5 120.80(16) . . ? C7 C6 H6 119.6 . . ? C5 C6 H6 119.6 . . ? N3 C7 C6 126.75(17) . . ? N3 C7 H7 116.6 . . ? C6 C7 H7 116.6 . . ? N3 C8 H8A 109.5 . . ? N3 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? N3 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? N3 C9 H9A 109.5 . . ? N3 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? N3 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C11 C10 C4 121.85(16) . . ? C11 C10 H10 119.1 . . ? C4 C10 H10 119.1 . . ? N2 C11 C10 128.10(17) . . ? N2 C11 H11 116.0 . . ? C10 C11 H11 116.0 . . ? N2 C12 H12A 109.5 . . ? N2 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? N2 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? N2 C13 H13A 109.5 . . ? N2 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? N2 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? 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 O1 N1 C1 C2 -178.9(2) . . . . ? O2 N1 C1 C2 -1.6(3) . . . . ? O1 N1 C1 C5 -0.8(3) . . . . ? O2 N1 C1 C5 176.47(19) . . . . ? C5 C1 C2 C3 -3.3(3) . . . . ? N1 C1 C2 C3 174.92(17) . . . . ? C1 C2 C3 C4 -0.5(3) . . . . ? C5 N4 C4 C3 -3.5(2) . . . . ? C5 N4 C4 C10 175.51(15) . . . . ? C2 C3 C4 N4 4.0(3) . . . . ? C2 C3 C4 C10 -175.04(16) . . . . ? C4 N4 C5 C1 -0.4(2) . . . . ? C4 N4 C5 C6 178.66(15) . . . . ? C2 C1 C5 N4 3.8(2) . . . . ? N1 C1 C5 N4 -174.28(16) . . . . ? C2 C1 C5 C6 -175.17(16) . . . . ? N1 C1 C5 C6 6.8(3) . . . . ? N4 C5 C6 C7 3.3(2) . . . . ? C1 C5 C6 C7 -177.73(17) . . . . ? C8 N3 C7 C6 2.6(3) . . . . ? C9 N3 C7 C6 179.1(2) . . . . ? C5 C6 C7 N3 -176.79(17) . . . . ? N4 C4 C10 C11 -7.0(3) . . . . ? C3 C4 C10 C11 172.04(17) . . . . ? C12 N2 C11 C10 2.2(3) . . . . ? C13 N2 C11 C10 168.30(19) . . . . ? C4 C10 C11 N2 -178.86(17) . . . . ? _diffrn_measured_fraction_theta_max 0.968 _diffrn_reflns_theta_full 27.60 _diffrn_measured_fraction_theta_full 0.968 _refine_diff_density_max 0.303 _refine_diff_density_min -0.339 _refine_diff_density_rms 0.043 data_sl0347 _database_code_depnum_ccdc_archive 'CCDC 218709' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C13 H13 N3 O2' _chemical_formula_sum 'C13 H13 N3 O2' _chemical_formula_weight 243.26 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 Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.7972(7) _cell_length_b 11.4319(8) _cell_length_c 11.7065(8) _cell_angle_alpha 105.934(2) _cell_angle_beta 112.814(3) _cell_angle_gamma 101.936(3) _cell_volume 1198.09(14) _cell_formula_units_Z 4 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 23037 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 25.03 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.46 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.349 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 512 _exptl_absorpt_coefficient_mu 0.094 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.892 _exptl_absorpt_correction_T_max 0.998 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _exptl_special_details ; Poor (split) crystals: some spots overlapped. This is the best of three separate datasets. ; _diffrn_ambient_temperature 180(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_measurement_method 'Thin slice \w and \f scans' _diffrn_reflns_number 9991 _diffrn_reflns_av_R_equivalents 0.0685 _diffrn_reflns_av_sigmaI/netI 0.0853 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 3.63 _diffrn_reflns_theta_max 24.94 _reflns_number_total 4120 _reflns_number_gt 2688 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V. 1998)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction ; HKL Denzo and Scalepack (Otwinowski & Minor 1997) ; _computing_structure_solution 'SIR-92 (Altomare et al. 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick 1997)' _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^)+(0.0919P)^2^+3.2548P] 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 4120 _refine_ls_number_parameters 329 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1476 _refine_ls_R_factor_gt 0.1003 _refine_ls_wR_factor_ref 0.2837 _refine_ls_wR_factor_gt 0.2571 _refine_ls_goodness_of_fit_ref 1.153 _refine_ls_restrained_S_all 1.153 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1_1 O 0.2786(5) 0.4288(4) -0.2733(4) 0.0594(12) Uani 1 1 d . . . O2_1 O 0.2811(5) 0.2587(5) -0.4064(4) 0.0598(12) Uani 1 1 d . . . N1_1 N 0.2303(5) 0.3422(4) -0.3838(4) 0.0359(11) Uani 1 1 d . . . N2_1 N -0.2868(5) 0.1437(4) -0.6966(4) 0.0424(12) Uani 1 1 d . . . N3_1 N 0.4085(5) 0.6929(5) -0.5309(5) 0.0469(12) Uani 1 1 d . . . C1_1 C 0.1011(5) 0.3372(5) -0.4969(4) 0.0303(11) Uani 1 1 d . . . C2_1 C -0.0295(6) 0.2419(5) -0.5361(5) 0.0336(12) Uani 1 1 d . . . C3_1 C -0.0483(6) 0.1534(5) -0.4758(6) 0.0416(14) Uani 1 1 d . . . H3_1 H 0.0312 0.1562 -0.4003 0.050 Uiso 1 1 calc R . . C4_1 C -0.1802(6) 0.0643(6) -0.5258(6) 0.0464(14) Uani 1 1 d . . . H4_1 H -0.1938 0.0041 -0.4858 0.056 Uiso 1 1 calc R . . C5_1 C -0.2967(6) 0.0615(6) -0.6371(6) 0.0450(14) Uani 1 1 d . . . H5_1 H -0.3878 -0.0031 -0.6718 0.054 Uiso 1 1 calc R . . C6_1 C -0.1531(5) 0.2348(5) -0.6474(5) 0.0344(12) Uani 1 1 d . . . C7_1 C -0.1380(6) 0.3214(5) -0.7092(5) 0.0394(13) Uani 1 1 d . . . H7_1 H -0.2202 0.3169 -0.7833 0.047 Uiso 1 1 calc R . . C8_1 C -0.0082(6) 0.4123(5) -0.6659(5) 0.0371(13) Uani 1 1 d . . . H8_1 H -0.0032 0.4700 -0.7102 0.044 Uiso 1 1 calc R . . C9_1 C 0.1199(5) 0.4241(5) -0.5570(5) 0.0332(12) Uani 1 1 d . . . C10_1 C 0.2592(6) 0.5197(5) -0.5109(5) 0.0385(13) Uani 1 1 d . . . H10_1 H 0.3393 0.5231 -0.4356 0.046 Uiso 1 1 calc R . . C11_1 C 0.2821(6) 0.6040(5) -0.5684(5) 0.0396(13) Uani 1 1 d . . . H11_1 H 0.2006 0.6000 -0.6427 0.048 Uiso 1 1 calc R . . C12_1 C 0.4132(8) 0.7895(6) -0.5902(7) 0.0565(17) Uani 1 1 d . . . H12A_1 H 0.3211 0.7629 -0.6706 0.085 Uiso 1 1 calc R . . H12B_1 H 0.4903 0.7963 -0.6153 0.085 Uiso 1 1 calc R . . H12C_1 H 0.4315 0.8740 -0.5245 0.085 Uiso 1 1 calc R . . C13_1 C 0.5349(6) 0.7128(6) -0.4123(6) 0.0501(15) Uani 1 1 d . . . H13A_1 H 0.5523 0.6307 -0.4215 0.075 Uiso 1 1 calc R . . H13B_1 H 0.5207 0.7430 -0.3330 0.075 Uiso 1 1 calc R . . H13C_1 H 0.6177 0.7782 -0.4017 0.075 Uiso 1 1 calc R . . O1_2 O 0.3142(5) -0.2019(4) -0.9110(4) 0.0618(13) Uani 1 1 d . . . O2_2 O 0.3235(5) -0.0293(4) -0.7699(4) 0.0573(12) Uani 1 1 d . . . N1_2 N 0.2806(5) -0.1073(4) -0.8845(4) 0.0344(10) Uani 1 1 d . . . N2_2 N 0.1892(5) 0.1358(4) -1.1760(4) 0.0409(11) Uani 1 1 d . . . N3_2 N -0.2086(5) -0.4460(5) -1.0616(5) 0.0492(13) Uani 1 1 d . . . C1_2 C 0.1808(5) -0.0836(5) -0.9973(5) 0.0320(12) Uani 1 1 d . . . C2_2 C 0.2401(5) 0.0187(5) -1.0264(5) 0.0314(11) Uani 1 1 d . . . C3_2 C 0.3876(6) 0.0979(5) -0.9596(5) 0.0382(13) Uani 1 1 d . . . H3_2 H 0.4557 0.0856 -0.8873 0.046 Uiso 1 1 calc R . . C4_2 C 0.4292(6) 0.1914(5) -1.0014(5) 0.0412(13) Uani 1 1 d . . . H4_2 H 0.5269 0.2468 -0.9567 0.049 Uiso 1 1 calc R . . C5_2 C 0.3279(6) 0.2065(5) -1.1103(5) 0.0437(14) Uani 1 1 d . . . H5_2 H 0.3608 0.2714 -1.1386 0.052 Uiso 1 1 calc R . . C6_2 C 0.1442(5) 0.0416(5) -1.1353(5) 0.0328(12) Uani 1 1 d . . . C7_2 C -0.0027(6) -0.0372(5) -1.2048(5) 0.0381(13) Uani 1 1 d . . . H7_2 H -0.0673 -0.0231 -1.2778 0.046 Uiso 1 1 calc R . . C8_2 C -0.0532(6) -0.1327(5) -1.1690(5) 0.0389(13) Uani 1 1 d . . . H8_2 H -0.1530 -0.1827 -1.2176 0.047 Uiso 1 1 calc R . . C9_2 C 0.0367(5) -0.1614(5) -1.0621(5) 0.0331(12) Uani 1 1 d . . . C10_2 C -0.0185(6) -0.2617(5) -1.0231(5) 0.0390(13) Uani 1 1 d . . . H10_2 H 0.0446 -0.2656 -0.9419 0.047 Uiso 1 1 calc R . . C11_2 C -0.1536(6) -0.3503(5) -1.0941(5) 0.0413(13) Uani 1 1 d . . . H11_2 H -0.2159 -0.3447 -1.1746 0.050 Uiso 1 1 calc R . . C12_2 C -0.3636(7) -0.5126(6) -1.1303(7) 0.0584(17) Uani 1 1 d . . . H12A_2 H -0.4057 -0.5048 -1.2173 0.088 Uiso 1 1 calc R . . H12B_2 H -0.4042 -0.4732 -1.0748 0.088 Uiso 1 1 calc R . . H12C_2 H -0.3851 -0.6047 -1.1450 0.088 Uiso 1 1 calc R . . C13_2 C -0.1296(7) -0.4504(6) -0.9321(6) 0.0527(16) Uani 1 1 d . . . H13A_2 H -0.0363 -0.4554 -0.9209 0.079 Uiso 1 1 calc R . . H13B_2 H -0.1841 -0.5271 -0.9271 0.079 Uiso 1 1 calc R . . H13C_2 H -0.1147 -0.3717 -0.8604 0.079 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 O1_1 0.063(3) 0.060(3) 0.027(2) 0.009(2) 0.0002(19) 0.019(2) O2_1 0.056(3) 0.075(3) 0.062(3) 0.033(2) 0.025(2) 0.046(3) N1_1 0.035(2) 0.043(3) 0.033(2) 0.019(2) 0.015(2) 0.016(2) N2_1 0.034(3) 0.043(3) 0.036(2) 0.007(2) 0.011(2) 0.012(2) N3_1 0.048(3) 0.050(3) 0.048(3) 0.028(2) 0.023(2) 0.014(2) C1_1 0.032(3) 0.037(3) 0.021(2) 0.010(2) 0.011(2) 0.017(2) C2_1 0.037(3) 0.038(3) 0.028(3) 0.013(2) 0.014(2) 0.019(2) C3_1 0.033(3) 0.047(3) 0.042(3) 0.021(3) 0.013(3) 0.014(3) C4_1 0.043(3) 0.049(3) 0.047(3) 0.024(3) 0.018(3) 0.016(3) C5_1 0.036(3) 0.048(3) 0.049(3) 0.019(3) 0.018(3) 0.013(3) C6_1 0.032(3) 0.038(3) 0.029(3) 0.009(2) 0.013(2) 0.013(2) C7_1 0.040(3) 0.047(3) 0.029(3) 0.015(3) 0.010(2) 0.023(3) C8_1 0.042(3) 0.044(3) 0.029(3) 0.019(2) 0.014(2) 0.021(3) C9_1 0.035(3) 0.037(3) 0.027(3) 0.014(2) 0.012(2) 0.017(2) C10_1 0.037(3) 0.044(3) 0.034(3) 0.017(3) 0.014(2) 0.016(3) C11_1 0.040(3) 0.046(3) 0.035(3) 0.019(3) 0.016(2) 0.017(3) C12_1 0.066(4) 0.056(4) 0.073(4) 0.043(4) 0.043(4) 0.026(3) C13_1 0.049(4) 0.046(3) 0.041(3) 0.014(3) 0.014(3) 0.007(3) O1_2 0.070(3) 0.068(3) 0.063(3) 0.036(2) 0.028(2) 0.047(3) O2_2 0.063(3) 0.053(2) 0.030(2) 0.013(2) 0.0020(19) 0.017(2) N1_2 0.032(2) 0.035(2) 0.029(2) 0.014(2) 0.0087(19) 0.008(2) N2_2 0.045(3) 0.044(3) 0.039(2) 0.022(2) 0.020(2) 0.020(2) N3_2 0.039(3) 0.044(3) 0.051(3) 0.020(2) 0.012(2) 0.007(2) C1_2 0.035(3) 0.032(3) 0.029(3) 0.013(2) 0.012(2) 0.017(2) C2_2 0.032(3) 0.035(3) 0.028(3) 0.012(2) 0.013(2) 0.017(2) C3_2 0.031(3) 0.045(3) 0.034(3) 0.017(3) 0.010(2) 0.014(2) C4_2 0.035(3) 0.044(3) 0.040(3) 0.021(3) 0.013(2) 0.011(3) C5_2 0.045(4) 0.042(3) 0.039(3) 0.018(3) 0.017(3) 0.009(3) C6_2 0.029(3) 0.038(3) 0.029(3) 0.012(2) 0.010(2) 0.015(2) C7_2 0.040(3) 0.044(3) 0.031(3) 0.017(2) 0.013(2) 0.018(3) C8_2 0.030(3) 0.045(3) 0.030(3) 0.009(2) 0.009(2) 0.013(2) C9_2 0.034(3) 0.033(3) 0.027(3) 0.008(2) 0.011(2) 0.013(2) C10_2 0.040(3) 0.044(3) 0.036(3) 0.019(3) 0.018(3) 0.016(3) C11_2 0.042(3) 0.040(3) 0.037(3) 0.017(3) 0.015(3) 0.013(3) C12_2 0.046(4) 0.048(4) 0.062(4) 0.015(3) 0.019(3) 0.005(3) C13_2 0.051(4) 0.059(4) 0.055(4) 0.037(3) 0.023(3) 0.017(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_1 N1_1 1.219(5) . ? O2_1 N1_1 1.213(6) . ? N1_1 C1_1 1.482(6) . ? N2_1 C5_1 1.324(7) . ? N2_1 C6_1 1.380(7) . ? N3_1 C11_1 1.343(7) . ? N3_1 C13_1 1.439(7) . ? N3_1 C12_1 1.458(7) . ? C1_1 C9_1 1.391(7) . ? C1_1 C2_1 1.406(7) . ? C2_1 C3_1 1.407(8) . ? C2_1 C6_1 1.426(7) . ? C3_1 C4_1 1.355(8) . ? C3_1 H3_1 0.9500 . ? C4_1 C5_1 1.404(8) . ? C4_1 H4_1 0.9500 . ? C5_1 H5_1 0.9500 . ? C6_1 C7_1 1.397(8) . ? C7_1 C8_1 1.363(8) . ? C7_1 H7_1 0.9500 . ? C8_1 C9_1 1.420(7) . ? C8_1 H8_1 0.9500 . ? C9_1 C10_1 1.454(7) . ? C10_1 C11_1 1.352(8) . ? C10_1 H10_1 0.9500 . ? C11_1 H11_1 0.9500 . ? C12_1 H12A_1 0.9800 . ? C12_1 H12B_1 0.9800 . ? C12_1 H12C_1 0.9800 . ? C13_1 H13A_1 0.9800 . ? C13_1 H13B_1 0.9800 . ? C13_1 H13C_1 0.9800 . ? O1_2 N1_2 1.210(6) . ? O2_2 N1_2 1.224(5) . ? N1_2 C1_2 1.480(6) . ? N2_2 C5_2 1.324(7) . ? N2_2 C6_2 1.367(7) . ? N3_2 C11_2 1.353(7) . ? N3_2 C13_2 1.444(7) . ? N3_2 C12_2 1.456(8) . ? C1_2 C9_2 1.388(7) . ? C1_2 C2_2 1.405(7) . ? C2_2 C3_2 1.420(7) . ? C2_2 C6_2 1.428(7) . ? C3_2 C4_2 1.358(8) . ? C3_2 H3_2 0.9500 . ? C4_2 C5_2 1.403(8) . ? C4_2 H4_2 0.9500 . ? C5_2 H5_2 0.9500 . ? C6_2 C7_2 1.412(7) . ? C7_2 C8_2 1.359(8) . ? C7_2 H7_2 0.9500 . ? C8_2 C9_2 1.426(7) . ? C8_2 H8_2 0.9500 . ? C9_2 C10_2 1.447(8) . ? C10_2 C11_2 1.354(8) . ? C10_2 H10_2 0.9500 . ? C11_2 H11_2 0.9500 . ? C12_2 H12A_2 0.9800 . ? C12_2 H12B_2 0.9800 . ? C12_2 H12C_2 0.9800 . ? C13_2 H13A_2 0.9800 . ? C13_2 H13B_2 0.9800 . ? C13_2 H13C_2 0.9800 . ? 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 O2_1 N1_1 O1_1 123.8(5) . . ? O2_1 N1_1 C1_1 117.9(4) . . ? O1_1 N1_1 C1_1 118.3(4) . . ? C5_1 N2_1 C6_1 117.5(5) . . ? C11_1 N3_1 C13_1 120.1(5) . . ? C11_1 N3_1 C12_1 120.2(5) . . ? C13_1 N3_1 C12_1 118.3(5) . . ? C9_1 C1_1 C2_1 125.8(4) . . ? C9_1 C1_1 N1_1 117.6(4) . . ? C2_1 C1_1 N1_1 116.5(4) . . ? C1_1 C2_1 C3_1 125.8(5) . . ? C1_1 C2_1 C6_1 116.5(5) . . ? C3_1 C2_1 C6_1 117.7(5) . . ? C4_1 C3_1 C2_1 119.7(5) . . ? C4_1 C3_1 H3_1 120.2 . . ? C2_1 C3_1 H3_1 120.2 . . ? C3_1 C4_1 C5_1 119.6(6) . . ? C3_1 C4_1 H4_1 120.2 . . ? C5_1 C4_1 H4_1 120.2 . . ? N2_1 C5_1 C4_1 123.7(5) . . ? N2_1 C5_1 H5_1 118.1 . . ? C4_1 C5_1 H5_1 118.1 . . ? N2_1 C6_1 C7_1 119.1(5) . . ? N2_1 C6_1 C2_1 121.8(5) . . ? C7_1 C6_1 C2_1 119.0(5) . . ? C8_1 C7_1 C6_1 121.6(5) . . ? C8_1 C7_1 H7_1 119.2 . . ? C6_1 C7_1 H7_1 119.2 . . ? C7_1 C8_1 C9_1 122.6(5) . . ? C7_1 C8_1 H8_1 118.7 . . ? C9_1 C8_1 H8_1 118.7 . . ? C1_1 C9_1 C8_1 114.4(5) . . ? C1_1 C9_1 C10_1 122.5(5) . . ? C8_1 C9_1 C10_1 123.0(5) . . ? C11_1 C10_1 C9_1 124.2(5) . . ? C11_1 C10_1 H10_1 117.9 . . ? C9_1 C10_1 H10_1 117.9 . . ? N3_1 C11_1 C10_1 126.7(5) . . ? N3_1 C11_1 H11_1 116.7 . . ? C10_1 C11_1 H11_1 116.7 . . ? N3_1 C12_1 H12A_1 109.5 . . ? N3_1 C12_1 H12B_1 109.5 . . ? H12A_1 C12_1 H12B_1 109.5 . . ? N3_1 C12_1 H12C_1 109.5 . . ? H12A_1 C12_1 H12C_1 109.5 . . ? H12B_1 C12_1 H12C_1 109.5 . . ? N3_1 C13_1 H13A_1 109.5 . . ? N3_1 C13_1 H13B_1 109.5 . . ? H13A_1 C13_1 H13B_1 109.5 . . ? N3_1 C13_1 H13C_1 109.5 . . ? H13A_1 C13_1 H13C_1 109.5 . . ? H13B_1 C13_1 H13C_1 109.5 . . ? O1_2 N1_2 O2_2 124.2(4) . . ? O1_2 N1_2 C1_2 118.3(4) . . ? O2_2 N1_2 C1_2 117.4(4) . . ? C5_2 N2_2 C6_2 117.2(5) . . ? C11_2 N3_2 C13_2 120.7(5) . . ? C11_2 N3_2 C12_2 118.8(5) . . ? C13_2 N3_2 C12_2 116.4(5) . . ? C9_2 C1_2 C2_2 125.8(5) . . ? C9_2 C1_2 N1_2 117.4(4) . . ? C2_2 C1_2 N1_2 116.8(4) . . ? C1_2 C2_2 C3_2 125.5(5) . . ? C1_2 C2_2 C6_2 116.9(5) . . ? C3_2 C2_2 C6_2 117.6(5) . . ? C4_2 C3_2 C2_2 118.6(5) . . ? C4_2 C3_2 H3_2 120.7 . . ? C2_2 C3_2 H3_2 120.7 . . ? C3_2 C4_2 C5_2 120.1(5) . . ? C3_2 C4_2 H4_2 120.0 . . ? C5_2 C4_2 H4_2 120.0 . . ? N2_2 C5_2 C4_2 123.9(5) . . ? N2_2 C5_2 H5_2 118.0 . . ? C4_2 C5_2 H5_2 118.0 . . ? N2_2 C6_2 C7_2 118.7(5) . . ? N2_2 C6_2 C2_2 122.6(5) . . ? C7_2 C6_2 C2_2 118.7(5) . . ? C8_2 C7_2 C6_2 121.2(5) . . ? C8_2 C7_2 H7_2 119.4 . . ? C6_2 C7_2 H7_2 119.4 . . ? C7_2 C8_2 C9_2 123.0(5) . . ? C7_2 C8_2 H8_2 118.5 . . ? C9_2 C8_2 H8_2 118.5 . . ? C1_2 C9_2 C8_2 114.4(5) . . ? C1_2 C9_2 C10_2 123.0(5) . . ? C8_2 C9_2 C10_2 122.6(5) . . ? C11_2 C10_2 C9_2 124.6(5) . . ? C11_2 C10_2 H10_2 117.7 . . ? C9_2 C10_2 H10_2 117.7 . . ? N3_2 C11_2 C10_2 126.3(5) . . ? N3_2 C11_2 H11_2 116.9 . . ? C10_2 C11_2 H11_2 116.9 . . ? N3_2 C12_2 H12A_2 109.5 . . ? N3_2 C12_2 H12B_2 109.5 . . ? H12A_2 C12_2 H12B_2 109.5 . . ? N3_2 C12_2 H12C_2 109.5 . . ? H12A_2 C12_2 H12C_2 109.5 . . ? H12B_2 C12_2 H12C_2 109.5 . . ? N3_2 C13_2 H13A_2 109.5 . . ? N3_2 C13_2 H13B_2 109.5 . . ? H13A_2 C13_2 H13B_2 109.5 . . ? N3_2 C13_2 H13C_2 109.5 . . ? H13A_2 C13_2 H13C_2 109.5 . . ? H13B_2 C13_2 H13C_2 109.5 . . ? 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 O2_1 N1_1 C1_1 C9_1 -103.1(6) . . . . ? O1_1 N1_1 C1_1 C9_1 77.7(6) . . . . ? O2_1 N1_1 C1_1 C2_1 75.3(6) . . . . ? O1_1 N1_1 C1_1 C2_1 -103.9(5) . . . . ? C9_1 C1_1 C2_1 C3_1 179.6(5) . . . . ? N1_1 C1_1 C2_1 C3_1 1.3(7) . . . . ? C9_1 C1_1 C2_1 C6_1 -0.1(7) . . . . ? N1_1 C1_1 C2_1 C6_1 -178.3(4) . . . . ? C1_1 C2_1 C3_1 C4_1 -178.5(5) . . . . ? C6_1 C2_1 C3_1 C4_1 1.2(8) . . . . ? C2_1 C3_1 C4_1 C5_1 -0.1(9) . . . . ? C6_1 N2_1 C5_1 C4_1 1.6(8) . . . . ? C3_1 C4_1 C5_1 N2_1 -1.4(9) . . . . ? C5_1 N2_1 C6_1 C7_1 178.7(5) . . . . ? C5_1 N2_1 C6_1 C2_1 -0.4(7) . . . . ? C1_1 C2_1 C6_1 N2_1 178.8(4) . . . . ? C3_1 C2_1 C6_1 N2_1 -0.9(7) . . . . ? C1_1 C2_1 C6_1 C7_1 -0.4(7) . . . . ? C3_1 C2_1 C6_1 C7_1 179.9(5) . . . . ? N2_1 C6_1 C7_1 C8_1 -179.2(5) . . . . ? C2_1 C6_1 C7_1 C8_1 0.0(8) . . . . ? C6_1 C7_1 C8_1 C9_1 0.9(8) . . . . ? C2_1 C1_1 C9_1 C8_1 0.9(7) . . . . ? N1_1 C1_1 C9_1 C8_1 179.1(4) . . . . ? C2_1 C1_1 C9_1 C10_1 -179.7(5) . . . . ? N1_1 C1_1 C9_1 C10_1 -1.4(7) . . . . ? C7_1 C8_1 C9_1 C1_1 -1.3(7) . . . . ? C7_1 C8_1 C9_1 C10_1 179.3(5) . . . . ? C1_1 C9_1 C10_1 C11_1 178.7(5) . . . . ? C8_1 C9_1 C10_1 C11_1 -1.9(8) . . . . ? C13_1 N3_1 C11_1 C10_1 -5.3(9) . . . . ? C12_1 N3_1 C11_1 C10_1 -171.3(6) . . . . ? C9_1 C10_1 C11_1 N3_1 -179.1(5) . . . . ? O1_2 N1_2 C1_2 C9_2 75.1(6) . . . . ? O2_2 N1_2 C1_2 C9_2 -104.7(5) . . . . ? O1_2 N1_2 C1_2 C2_2 -106.8(6) . . . . ? O2_2 N1_2 C1_2 C2_2 73.3(6) . . . . ? C9_2 C1_2 C2_2 C3_2 180.0(5) . . . . ? N1_2 C1_2 C2_2 C3_2 2.1(7) . . . . ? C9_2 C1_2 C2_2 C6_2 -2.2(7) . . . . ? N1_2 C1_2 C2_2 C6_2 179.9(4) . . . . ? C1_2 C2_2 C3_2 C4_2 178.5(5) . . . . ? C6_2 C2_2 C3_2 C4_2 0.8(7) . . . . ? C2_2 C3_2 C4_2 C5_2 -1.4(8) . . . . ? C6_2 N2_2 C5_2 C4_2 -1.0(8) . . . . ? C3_2 C4_2 C5_2 N2_2 1.6(9) . . . . ? C5_2 N2_2 C6_2 C7_2 -178.9(5) . . . . ? C5_2 N2_2 C6_2 C2_2 0.3(7) . . . . ? C1_2 C2_2 C6_2 N2_2 -178.1(5) . . . . ? C3_2 C2_2 C6_2 N2_2 -0.2(7) . . . . ? C1_2 C2_2 C6_2 C7_2 1.0(7) . . . . ? C3_2 C2_2 C6_2 C7_2 179.0(5) . . . . ? N2_2 C6_2 C7_2 C8_2 179.6(5) . . . . ? C2_2 C6_2 C7_2 C8_2 0.4(8) . . . . ? C6_2 C7_2 C8_2 C9_2 -0.9(8) . . . . ? C2_2 C1_2 C9_2 C8_2 1.8(7) . . . . ? N1_2 C1_2 C9_2 C8_2 179.7(4) . . . . ? C2_2 C1_2 C9_2 C10_2 -177.1(5) . . . . ? N1_2 C1_2 C9_2 C10_2 0.7(7) . . . . ? C7_2 C8_2 C9_2 C1_2 -0.1(7) . . . . ? C7_2 C8_2 C9_2 C10_2 178.8(5) . . . . ? C1_2 C9_2 C10_2 C11_2 -170.9(5) . . . . ? C8_2 C9_2 C10_2 C11_2 10.3(8) . . . . ? C13_2 N3_2 C11_2 C10_2 9.1(9) . . . . ? C12_2 N3_2 C11_2 C10_2 165.5(6) . . . . ? C9_2 C10_2 C11_2 N3_2 179.4(5) . . . . ? _diffrn_measured_fraction_theta_max 0.981 _diffrn_reflns_theta_full 24.94 _diffrn_measured_fraction_theta_full 0.981 _refine_diff_density_max 0.421 _refine_diff_density_min -0.340 _refine_diff_density_rms 0.079 data_sl0350 _database_code_depnum_ccdc_archive 'CCDC 220449' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C13 H14 N4 O2' _chemical_formula_sum 'C13 H14 N4 O2' _chemical_formula_weight 258.28 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 Monoclinic _symmetry_space_group_name_H-M C2/c 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' '-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 8.9586(5) _cell_length_b 16.1012(9) _cell_length_c 18.1413(10) _cell_angle_alpha 90.00 _cell_angle_beta 97.258(2) _cell_angle_gamma 90.00 _cell_volume 2595.8(3) _cell_formula_units_Z 8 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 49007 _cell_measurement_theta_min 1.02 _cell_measurement_theta_max 25.03 _exptl_crystal_description ? _exptl_crystal_colour colourless _exptl_crystal_size_max 0.39 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_min 0.23 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.322 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1088 _exptl_absorpt_coefficient_mu 0.093 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.884 _exptl_absorpt_correction_T_max 0.980 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _exptl_special_details ; The -OEt group is poorly resolved, disordered over at least two sites. Common, isotropic temperature factors plus bond length restraints were applied to this group for the refinement. ; _diffrn_ambient_temperature 180(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_measurement_method 'Thin slice \w and \f scans' _diffrn_reflns_number 9415 _diffrn_reflns_av_R_equivalents 0.0380 _diffrn_reflns_av_sigmaI/netI 0.0374 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 3.65 _diffrn_reflns_theta_max 25.01 _reflns_number_total 2282 _reflns_number_gt 1700 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V. 1998)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction ; HKL Denzo and Scalepack (Otwinowski & Minor 1997) ; _computing_structure_solution 'SIR-92 (Altomare et al. 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick 1997)' _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^)+(0.2000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.005(6) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2282 _refine_ls_number_parameters 173 _refine_ls_number_restraints 10 _refine_ls_R_factor_all 0.1272 _refine_ls_R_factor_gt 0.1086 _refine_ls_wR_factor_ref 0.3693 _refine_ls_wR_factor_gt 0.3476 _refine_ls_goodness_of_fit_ref 1.575 _refine_ls_restrained_S_all 1.636 _refine_ls_shift/su_max 0.432 _refine_ls_shift/su_mean 0.044 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 N1 N 0.1668(4) -0.03009(19) 0.29726(18) 0.0546(10) Uani 1 1 d . . . H1N H 0.2003 -0.0456 0.2558 0.066 Uiso 1 1 calc R . . O1 O 0.2828(5) 0.2002(2) 0.1936(2) 0.0989(14) Uani 1 1 d . A . C1 C 0.1188(4) -0.0817(2) 0.3490(2) 0.0564(11) Uani 1 1 d . . . H1 H 0.1161 -0.1405 0.3449 0.068 Uiso 1 1 calc R . . N2 N 0.0647(3) 0.11355(17) 0.43007(16) 0.0480(9) Uani 1 1 d . . . C2 C 0.0757(5) -0.0391(2) 0.4066(2) 0.0525(11) Uani 1 1 d . . . H2 H 0.0389 -0.0617 0.4492 0.063 Uiso 1 1 calc R . . N3 N 0.0610(4) 0.25772(16) 0.44264(18) 0.0538(10) Uani 1 1 d . . . C3 C 0.0962(4) 0.0462(2) 0.3909(2) 0.0457(10) Uani 1 1 d . . . C4 C 0.0897(4) 0.1877(2) 0.4017(2) 0.0443(10) Uani 1 1 d . . . N4 N 0.2267(5) 0.3456(2) 0.3013(2) 0.0808(14) Uani 1 1 d . . . C5 C 0.0389(5) 0.2426(2) 0.5207(2) 0.0644(13) Uani 1 1 d . . . H5A H 0.1162 0.2042 0.5433 0.097 Uiso 1 1 calc R . . H5B H -0.0609 0.2184 0.5226 0.097 Uiso 1 1 calc R . . H5C H 0.0466 0.2953 0.5480 0.097 Uiso 1 1 calc R . . C6 C -0.0461(6) 0.3189(3) 0.4102(3) 0.0833(16) Uani 1 1 d . . . H6A H -0.0500 0.3177 0.3559 0.125 Uiso 1 1 calc R . . H6B H -0.0150 0.3742 0.4287 0.125 Uiso 1 1 calc R . . H6C H -0.1460 0.3061 0.4239 0.125 Uiso 1 1 calc R . . C7 C 0.1532(4) 0.1972(2) 0.3338(2) 0.0491(10) Uani 1 1 d . . . C8 C 0.1846(4) 0.1268(2) 0.29163(19) 0.0513(11) Uani 1 1 d . A . C9 C 0.1537(4) 0.0503(2) 0.32096(19) 0.0470(10) Uani 1 1 d . . . C10 C 0.1957(5) 0.2787(2) 0.3135(2) 0.0600(12) Uani 1 1 d . . . C11 C 0.2524(6) 0.1358(3) 0.2209(2) 0.0696(13) Uani 1 1 d D . . O2 O 0.3263(12) 0.0634(5) 0.2038(5) 0.0615(13) Uiso 0.327(6) 1 d PD A 1 C12 C 0.344(2) 0.0822(13) 0.1250(8) 0.094(2) Uiso 0.327(6) 1 d PD A 1 H12A H 0.2624 0.0572 0.0904 0.113 Uiso 0.327(6) 1 calc PR A 1 H12B H 0.3474 0.1428 0.1161 0.113 Uiso 0.327(6) 1 calc PR A 1 C13 C 0.478(2) 0.0462(17) 0.1187(13) 0.101(2) Uiso 0.327(6) 1 d PD A 1 H13A H 0.4748 0.0205 0.0695 0.152 Uiso 0.327(6) 1 calc PR A 1 H13B H 0.4992 0.0035 0.1571 0.152 Uiso 0.327(6) 1 calc PR A 1 H13C H 0.5577 0.0883 0.1248 0.152 Uiso 0.327(6) 1 calc PR A 1 O2' O 0.2455(6) 0.0637(3) 0.1845(2) 0.0615(13) Uiso 0.673(6) 1 d PD A 2 C12' C 0.2981(10) 0.0551(6) 0.1122(5) 0.094(2) Uiso 0.673(6) 1 d PD A 2 H12C H 0.2621 0.0033 0.0865 0.113 Uiso 0.673(6) 1 calc PR A 2 H12D H 0.2712 0.1036 0.0796 0.113 Uiso 0.673(6) 1 calc PR A 2 C13' C 0.4521(12) 0.0525(8) 0.1384(6) 0.101(2) Uiso 0.673(6) 1 d PD A 2 H13D H 0.5089 0.0381 0.0974 0.152 Uiso 0.673(6) 1 calc PR A 2 H13E H 0.4702 0.0105 0.1776 0.152 Uiso 0.673(6) 1 calc PR A 2 H13F H 0.4848 0.1069 0.1584 0.152 Uiso 0.673(6) 1 calc PR A 2 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 N1 0.068(2) 0.0480(19) 0.0499(18) -0.0034(13) 0.0151(14) 0.0034(14) O1 0.152(4) 0.077(2) 0.078(2) 0.0114(17) 0.056(2) -0.013(2) C1 0.070(3) 0.038(2) 0.064(2) 0.0031(16) 0.0146(19) 0.0048(16) N2 0.0545(19) 0.0418(18) 0.0502(18) 0.0001(12) 0.0172(13) 0.0018(12) C2 0.069(3) 0.0364(19) 0.055(2) 0.0050(15) 0.0194(18) 0.0010(15) N3 0.070(2) 0.0374(17) 0.0554(19) -0.0019(13) 0.0128(15) 0.0036(14) C3 0.053(2) 0.0381(19) 0.048(2) 0.0011(14) 0.0124(15) 0.0028(14) C4 0.049(2) 0.0377(19) 0.046(2) 0.0011(13) 0.0058(15) -0.0004(13) N4 0.123(4) 0.048(2) 0.074(3) 0.0093(18) 0.027(2) -0.019(2) C5 0.083(3) 0.053(2) 0.059(3) -0.0107(17) 0.018(2) 0.0052(19) C6 0.111(4) 0.065(3) 0.075(3) 0.003(2) 0.016(3) 0.032(3) C7 0.059(2) 0.042(2) 0.047(2) 0.0049(15) 0.0073(16) -0.0010(16) C8 0.065(3) 0.049(2) 0.041(2) 0.0015(14) 0.0125(16) -0.0008(16) C9 0.057(2) 0.039(2) 0.045(2) -0.0029(14) 0.0093(16) 0.0039(14) C10 0.082(3) 0.048(2) 0.051(2) 0.0019(18) 0.0132(19) -0.0091(19) C11 0.094(3) 0.065(3) 0.053(2) 0.010(2) 0.022(2) -0.008(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 N1 C1 1.363(5) . ? N1 C9 1.373(5) . ? N1 H1N 0.8800 . ? O1 C11 1.195(6) . ? C1 C2 1.346(5) . ? C1 H1 0.9500 . ? N2 C4 1.330(4) . ? N2 C3 1.345(4) . ? C2 C3 1.419(5) . ? C2 H2 0.9500 . ? N3 C4 1.392(4) . ? N3 C6 1.447(5) . ? N3 C5 1.474(5) . ? C3 C9 1.431(5) . ? C4 C7 1.428(5) . ? N4 C10 1.142(5) . ? C5 H5A 0.9800 . ? C5 H5B 0.9800 . ? C5 H5C 0.9800 . ? C6 H6A 0.9800 . ? C6 H6B 0.9800 . ? C6 H6C 0.9800 . ? C7 C8 1.415(5) . ? C7 C10 1.428(5) . ? C8 C9 1.384(5) . ? C8 C11 1.495(6) . ? C11 O2' 1.333(6) . ? C11 O2 1.394(9) . ? O2 C12 1.489(15) . ? C12 C13 1.350(18) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? O2' C12' 1.455(9) . ? C12' C13' 1.402(12) . ? C12' H12C 0.9900 . ? C12' H12D 0.9900 . ? C13' H13D 0.9800 . ? C13' H13E 0.9800 . ? C13' H13F 0.9800 . ? 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 C1 N1 C9 108.2(3) . . ? C1 N1 H1N 125.9 . . ? C9 N1 H1N 125.9 . . ? C2 C1 N1 111.7(3) . . ? C2 C1 H1 124.1 . . ? N1 C1 H1 124.1 . . ? C4 N2 C3 117.5(3) . . ? C1 C2 C3 106.3(3) . . ? C1 C2 H2 126.8 . . ? C3 C2 H2 126.9 . . ? C4 N3 C6 119.4(3) . . ? C4 N3 C5 115.8(3) . . ? C6 N3 C5 109.9(3) . . ? N2 C3 C2 129.3(3) . . ? N2 C3 C9 123.6(3) . . ? C2 C3 C9 107.0(3) . . ? N2 C4 N3 117.9(3) . . ? N2 C4 C7 122.3(3) . . ? N3 C4 C7 119.6(3) . . ? N3 C5 H5A 109.5 . . ? N3 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? N3 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? N3 C6 H6A 109.4 . . ? N3 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? N3 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? C8 C7 C10 121.2(3) . . ? C8 C7 C4 120.6(3) . . ? C10 C7 C4 118.0(3) . . ? C9 C8 C7 116.2(3) . . ? C9 C8 C11 122.6(3) . . ? C7 C8 C11 121.1(3) . . ? N1 C9 C8 133.6(4) . . ? N1 C9 C3 106.8(3) . . ? C8 C9 C3 119.6(3) . . ? N4 C10 C7 175.7(4) . . ? O1 C11 O2' 123.3(4) . . ? O1 C11 O2 119.6(5) . . ? O2' C11 O2 32.4(4) . . ? O1 C11 C8 125.3(4) . . ? O2' C11 C8 110.1(4) . . ? O2 C11 C8 111.5(5) . . ? C11 O2 C12 99.0(9) . . ? C13 C12 O2 101.5(14) . . ? C13 C12 H12A 111.2 . . ? O2 C12 H12A 111.1 . . ? C13 C12 H12B 111.8 . . ? O2 C12 H12B 111.7 . . ? H12A C12 H12B 109.3 . . ? C11 O2' C12' 122.0(5) . . ? C13' C12' O2' 96.6(7) . . ? C13' C12' H12C 112.3 . . ? O2' C12' H12C 112.4 . . ? C13' C12' H12D 112.5 . . ? O2' C12' H12D 112.5 . . ? H12C C12' H12D 110.0 . . ? C12' C13' H13D 109.6 . . ? C12' C13' H13E 109.5 . . ? H13D C13' H13E 109.5 . . ? C12' C13' H13F 109.3 . . ? H13D C13' H13F 109.5 . . ? H13E C13' H13F 109.5 . . ? 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 C9 N1 C1 C2 -0.6(5) . . . . ? N1 C1 C2 C3 0.4(4) . . . . ? C4 N2 C3 C2 -177.5(3) . . . . ? C4 N2 C3 C9 -0.3(5) . . . . ? C1 C2 C3 N2 177.5(4) . . . . ? C1 C2 C3 C9 0.0(4) . . . . ? C3 N2 C4 N3 -178.4(3) . . . . ? C3 N2 C4 C7 -2.6(5) . . . . ? C6 N3 C4 N2 -121.6(4) . . . . ? C5 N3 C4 N2 13.4(5) . . . . ? C6 N3 C4 C7 62.4(5) . . . . ? C5 N3 C4 C7 -162.5(3) . . . . ? N2 C4 C7 C8 3.7(5) . . . . ? N3 C4 C7 C8 179.5(3) . . . . ? N2 C4 C7 C10 -171.1(3) . . . . ? N3 C4 C7 C10 4.7(5) . . . . ? C10 C7 C8 C9 173.0(3) . . . . ? C4 C7 C8 C9 -1.6(5) . . . . ? C10 C7 C8 C11 -4.8(6) . . . . ? C4 C7 C8 C11 -179.4(4) . . . . ? C1 N1 C9 C8 -179.8(4) . . . . ? C1 N1 C9 C3 0.5(4) . . . . ? C7 C8 C9 N1 179.3(4) . . . . ? C11 C8 C9 N1 -2.9(7) . . . . ? C7 C8 C9 C3 -1.1(5) . . . . ? C11 C8 C9 C3 176.7(3) . . . . ? N2 C3 C9 N1 -178.1(3) . . . . ? C2 C3 C9 N1 -0.3(4) . . . . ? N2 C3 C9 C8 2.2(6) . . . . ? C2 C3 C9 C8 180.0(3) . . . . ? C8 C7 C10 N4 -175(6) . . . . ? C4 C7 C10 N4 0(6) . . . . ? C9 C8 C11 O1 -179.1(4) . . . . ? C7 C8 C11 O1 -1.4(8) . . . . ? C9 C8 C11 O2' 13.8(6) . . . . ? C7 C8 C11 O2' -168.5(4) . . . . ? C9 C8 C11 O2 -20.9(8) . . . . ? C7 C8 C11 O2 156.8(6) . . . . ? O1 C11 O2 C12 -34.5(11) . . . . ? O2' C11 O2 C12 72.0(11) . . . . ? C8 C11 O2 C12 165.9(9) . . . . ? C11 O2 C12 C13 145.7(17) . . . . ? O1 C11 O2' C12' 10.2(9) . . . . ? O2 C11 O2' C12' -83.7(9) . . . . ? C8 C11 O2' C12' 177.6(5) . . . . ? C11 O2' C12' C13' 77.4(9) . . . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 25.01 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 1.220 _refine_diff_density_min -0.727 _refine_diff_density_rms 0.083