# Copyright The Royal Society of Chemistry, 1999 # CCDC Number: 188/165 data_brch3 _audit_creation_method SHELXL _chemical_name_systematic ; ? ; _chemical_name_common 'compound 3a' _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C7 H10 Cl N3 O2' _chemical_formula_weight 203.63 _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' 'Cl' 'Cl' 0.1484 0.1585 '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 7.352(3) _cell_length_b 7.357(2) _cell_length_c 8.938(2) _cell_angle_alpha 87.39(2) _cell_angle_beta 100.03(3) _cell_angle_gamma 72.66(3) _cell_volume 452.0(2) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.56 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.496 _exptl_crystal_density_method ? _exptl_crystal_F_000 212 _exptl_absorpt_coefficient_mu 0.393 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoKa _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device ? _diffrn_measurement_method ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 2095 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0915 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.33 _diffrn_reflns_theta_max 27.49 _reflns_number_total 2095 _reflns_number_observed 1278 _reflns_observed_criterion >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement on F^2^ for ALL reflections except for 0 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R- factors wR and all goodnesses of fit S are based on F^2^, conventional R- factors R are based on F, with F set to zero for negative F^2^. The observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme 'calc w=1/[s^2^(Fo^2^)+( 0.0641P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment ? _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2095 _refine_ls_number_parameters 140 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0989 _refine_ls_R_factor_obs 0.0566 _refine_ls_wR_factor_all 0.1311 _refine_ls_wR_factor_obs 0.1204 _refine_ls_goodness_of_fit_all 0.945 _refine_ls_goodness_of_fit_obs 1.134 _refine_ls_restrained_S_all 0.945 _refine_ls_restrained_S_obs 1.134 _refine_ls_shift/esd_max -0.001 _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 N1 N 0.0860(4) -0.3363(4) -0.6524(3) 0.0331(6) Uani 1 d . . C2 C 0.2475(4) -0.3451(4) -0.7064(3) 0.0308(7) Uani 1 d . . C3 C 0.3771(4) -0.2863(4) -0.5991(3) 0.0282(6) Uani 1 d . . N4 N 0.2899(3) -0.2406(3) -0.4802(3) 0.0288(6) Uani 1 d . . C5 C 0.3461(5) -0.1715(5) -0.3435(3) 0.0357(7) Uani 1 d . . C6 C 0.2242(5) -0.1365(5) -0.2472(4) 0.0413(8) Uani 1 d . . N7 N 0.0479(4) -0.1681(4) -0.2805(3) 0.0379(7) Uani 1 d . . C8 C -0.0097(5) -0.2348(5) -0.4110(4) 0.0363(7) Uani 1 d . . C9 C 0.1104(4) -0.2736(4) -0.5139(4) 0.0308(7) Uani 1 d . . O10 O 0.5519(3) -0.2722(4) -0.5945(3) 0.0413(6) Uani 1 d . . C11 C 0.2725(5) -0.4053(5) -0.8602(4) 0.0414(8) Uani 1 d . . H11A H 0.1604(5) -0.4377(5) -0.9079(4) 0.090(5) Uiso 1 calc R . H11B H 0.3861(5) -0.5149(5) -0.8499(4) 0.090(5) Uiso 1 calc R . H11C H 0.2870(5) -0.3022(5) -0.9219(4) 0.090(5) Uiso 1 calc R . Cl12 Cl 0.27195(12) 0.08662(13) 0.10127(9) 0.0418(3) Uani 1 d . . O13 O 0.7249(4) -0.3446(4) -0.8112(3) 0.0436(6) Uani 1 d . . H5 H 0.4690(69) -0.1491(67) -0.3198(52) 0.090(5) Uiso 1 d . . H6 H 0.2539(64) -0.0850(65) -0.1487(53) 0.090(5) Uiso 1 d . . H7 H -0.0382(69) -0.1423(66) -0.2147(53) 0.090(5) Uiso 1 d . . H8 H -0.1346(71) -0.2531(64) -0.4318(51) 0.090(5) Uiso 1 d . . H10 H 0.5947(67) -0.2934(68) -0.6851(56) 0.090(5) Uiso 1 d . . H13A H 0.7000(66) -0.2659(69) -0.8946(57) 0.090(5) Uiso 1 d . . H13B H 0.8383(71) -0.3576(70) -0.7724(56) 0.090(5) 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 N1 0.0325(14) 0.039(2) 0.0312(14) -0.0059(12) 0.0032(11) -0.0168(12) C2 0.031(2) 0.032(2) 0.030(2) -0.0049(13) 0.0029(12) -0.0134(13) C3 0.0262(15) 0.034(2) 0.0248(14) -0.0013(12) 0.0023(12) -0.0121(13) N4 0.0253(12) 0.0347(14) 0.0265(13) -0.0024(11) 0.0006(10) -0.0124(11) C5 0.039(2) 0.042(2) 0.026(2) -0.0034(14) -0.0009(13) -0.017(2) C6 0.049(2) 0.042(2) 0.033(2) -0.008(2) 0.005(2) -0.016(2) N7 0.041(2) 0.042(2) 0.0330(15) -0.0049(12) 0.0118(12) -0.0138(13) C8 0.033(2) 0.036(2) 0.040(2) 0.0021(14) 0.0077(14) -0.0125(14) C9 0.0263(15) 0.031(2) 0.036(2) -0.0006(13) 0.0029(12) -0.0119(13) O10 0.0295(12) 0.063(2) 0.0368(13) -0.0073(11) 0.0058(10) -0.0227(11) C11 0.045(2) 0.048(2) 0.032(2) -0.013(2) 0.0058(15) -0.016(2) Cl12 0.0446(5) 0.0515(5) 0.0358(5) -0.0112(4) 0.0114(4) -0.0216(4) O13 0.0366(13) 0.063(2) 0.0370(13) -0.0053(12) 0.0079(11) -0.0234(13) _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 C2 1.342(4) . ? N1 C9 1.342(4) . ? C2 C3 1.407(4) . ? C2 C11 1.488(4) . ? C3 O10 1.313(4) . ? C3 N4 1.340(4) . ? N4 C5 1.388(4) . ? N4 C9 1.397(4) . ? C5 C6 1.328(5) . ? C5 H5 0.96(5) . ? C6 N7 1.369(4) . ? C6 H6 0.99(5) . ? N7 C8 1.336(4) . ? N7 H7 0.92(5) . ? C8 C9 1.365(5) . ? C8 H8 0.96(5) . ? O10 H10 0.92(5) . ? C11 H11A 0.96 . ? C11 H11B 0.96 . ? C11 H11C 0.96 . ? O13 H13A 0.88(5) . ? O13 H13B 0.82(5) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 N1 C9 106.5(2) . . ? N1 C2 C3 110.0(3) . . ? N1 C2 C11 122.2(3) . . ? C3 C2 C11 127.9(3) . . ? O10 C3 N4 119.4(2) . . ? O10 C3 C2 134.2(3) . . ? N4 C3 C2 106.4(2) . . ? C3 N4 C5 132.3(3) . . ? C3 N4 C9 107.2(2) . . ? C5 N4 C9 120.5(3) . . ? C6 C5 N4 118.2(3) . . ? C6 C5 H5 120.9(28) . . ? N4 C5 H5 120.8(28) . . ? C5 C6 N7 121.2(3) . . ? C5 C6 H6 122.5(27) . . ? N7 C6 H6 116.3(27) . . ? C8 N7 C6 121.8(3) . . ? C8 N7 H7 116.6(29) . . ? C6 N7 H7 121.6(29) . . ? N7 C8 C9 119.3(3) . . ? N7 C8 H8 119.8(27) . . ? C9 C8 H8 120.9(27) . . ? N1 C9 C8 131.1(3) . . ? N1 C9 N4 110.0(3) . . ? C8 C9 N4 118.9(3) . . ? C3 O10 H10 113.3(28) . . ? C2 C11 H11A 109.5(2) . . ? C2 C11 H11B 109.5(2) . . ? H11A C11 H11B 109.5 . . ? C2 C11 H11C 109.5(2) . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? H13A O13 H13B 104.9(43) . . ? 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 C2 C3 -0.1(4) . . . . ? C9 N1 C2 C11 -178.7(3) . . . . ? N1 C2 C3 O10 178.5(3) . . . . ? C11 C2 C3 O10 -2.9(6) . . . . ? N1 C2 C3 N4 -0.5(4) . . . . ? C11 C2 C3 N4 178.1(3) . . . . ? O10 C3 N4 C5 2.0(5) . . . . ? C2 C3 N4 C5 -178.8(3) . . . . ? O10 C3 N4 C9 -178.4(3) . . . . ? C2 C3 N4 C9 0.8(3) . . . . ? C3 N4 C5 C6 179.0(3) . . . . ? C9 N4 C5 C6 -0.6(5) . . . . ? N4 C5 C6 N7 0.3(5) . . . . ? C5 C6 N7 C8 -0.2(5) . . . . ? C6 N7 C8 C9 0.3(5) . . . . ? C2 N1 C9 C8 178.3(3) . . . . ? C2 N1 C9 N4 0.5(3) . . . . ? N7 C8 C9 N1 -178.2(3) . . . . ? N7 C8 C9 N4 -0.6(5) . . . . ? C3 N4 C9 N1 -0.8(3) . . . . ? C5 N4 C9 N1 178.8(3) . . . . ? C3 N4 C9 C8 -178.9(3) . . . . ? C5 N4 C9 C8 0.7(4) . . . . ? _refine_diff_density_max 0.289 _refine_diff_density_min -0.274 _refine_diff_density_rms 0.068 data_br4-04 _audit_creation_method SHELXL _chemical_name_systematic ; ? ; _chemical_name_common 'compound 3b' _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C12 H13 N3 O3' _chemical_formula_weight 247.25 _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' 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting 'Triclinic' _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 6.832(2) _cell_length_b 9.076(6) _cell_length_c 9.679(3) _cell_angle_alpha 87.86(4) _cell_angle_beta 101.21(3) _cell_angle_gamma 88.92(4) _cell_volume 588.1(5) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.396 _exptl_crystal_density_method ? _exptl_crystal_F_000 260 _exptl_absorpt_coefficient_mu 0.856 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuKa _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device ? _diffrn_measurement_method ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 2126 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0440 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 4.66 _diffrn_reflns_theta_max 67.47 _reflns_number_total 2126 _reflns_number_observed 1529 _reflns_observed_criterion >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement on F^2^ for ALL reflections except for 0 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R- factors wR and all goodnesses of fit S are based on F^2^, conventional R- factors R are based on F, with F set to zero for negative F^2^. The observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme 'calc w=1/[s^2^(Fo^2^)+( 0.1022P)^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 SHELXL _refine_ls_extinction_coef 0.0134(25) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^l^3^/sin(2q)]^-1/4^' _refine_ls_number_reflns 2126 _refine_ls_number_parameters 204 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0754 _refine_ls_R_factor_obs 0.0561 _refine_ls_wR_factor_all 0.1533 _refine_ls_wR_factor_obs 0.1447 _refine_ls_goodness_of_fit_all 1.002 _refine_ls_goodness_of_fit_obs 1.137 _refine_ls_restrained_S_all 1.002 _refine_ls_restrained_S_obs 1.137 _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 N1 N 0.2185(3) 1.0766(2) 0.4520(2) 0.0392(5) Uani 1 d . . C2 C 0.2666(3) 1.0402(3) 0.5906(2) 0.0367(5) Uani 1 d . . C3 C 0.2995(3) 0.8832(3) 0.6159(2) 0.0362(5) Uani 1 d . . N4 N 0.2710(3) 0.8316(2) 0.4828(2) 0.0362(5) Uani 1 d . . C5 C 0.2836(4) 0.6891(3) 0.4365(3) 0.0442(6) Uani 1 d . . C6 C 0.2452(4) 0.6687(3) 0.2983(3) 0.0463(6) Uani 1 d . . N7 N 0.1904(3) 0.7850(2) 0.2026(2) 0.0440(5) Uani 1 d . . C8 C 0.1796(4) 0.9239(3) 0.2451(3) 0.0415(6) Uani 1 d . . C9 C 0.2193(3) 0.9499(3) 0.3842(2) 0.0369(5) Uani 1 d . . O10 O 0.3462(3) 0.8017(2) 0.7260(2) 0.0486(5) Uani 1 d . . C11 C 0.2809(3) 1.1515(3) 0.6974(2) 0.0387(6) Uani 1 d . . C12 C 0.3389(4) 1.1136(3) 0.8403(3) 0.0490(7) Uani 1 d . . C13 C 0.3515(5) 1.2197(4) 0.9398(3) 0.0593(8) Uani 1 d . . C14 C 0.3061(5) 1.3662(4) 0.8988(3) 0.0590(8) Uani 1 d . . C15 C 0.2494(5) 1.4053(4) 0.7584(3) 0.0585(8) Uani 1 d . . C16 C 0.2365(4) 1.2991(3) 0.6573(3) 0.0483(6) Uani 1 d . . O17 O 0.2650(3) 1.3179(2) 0.2675(2) 0.0545(5) Uani 1 d . . O18 O 0.0959(4) 0.7532(3) 0.9186(2) 0.0658(7) Uani 1 d . . H5 H 0.3271(47) 0.6094(38) 0.5139(35) 0.075(3) Uiso 1 d . . H6 H 0.2515(49) 0.5720(40) 0.2688(35) 0.075(3) Uiso 1 d . . H7 H 0.1715(48) 0.7745(38) 0.1027(37) 0.075(3) Uiso 1 d . . H8 H 0.1470(50) 1.0035(39) 0.1745(36) 0.075(3) Uiso 1 d . . H12 H 0.3694(51) 1.0131(40) 0.8703(35) 0.075(3) Uiso 1 d . . H13 H 0.3809(49) 1.1887(36) 1.0408(36) 0.075(3) Uiso 1 d . . H14 H 0.3112(51) 1.4374(38) 0.9734(35) 0.075(3) Uiso 1 d . . H15 H 0.2123(49) 1.5114(39) 0.7214(34) 0.075(3) Uiso 1 d . . H16 H 0.2017(49) 1.3277(39) 0.5528(37) 0.075(3) Uiso 1 d . . H17A H 0.2405(51) 1.2614(40) 0.3447(39) 0.075(3) Uiso 1 d . . H17B H 0.3808(56) 1.2943(40) 0.2508(36) 0.075(3) Uiso 1 d . . H18A H -0.0228(53) 0.7175(38) 0.8650(37) 0.075(3) Uiso 1 d . . H18B H 0.1729(52) 0.7651(39) 0.8554(38) 0.075(3) 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 N1 0.0437(11) 0.0399(11) 0.0345(10) -0.0062(8) 0.0082(8) 0.0021(8) C2 0.0352(12) 0.0447(13) 0.0312(11) -0.0062(10) 0.0085(9) 0.0022(9) C3 0.0358(12) 0.0435(13) 0.0302(11) -0.0029(9) 0.0086(9) 0.0046(9) N4 0.0384(10) 0.0382(11) 0.0330(10) -0.0033(8) 0.0095(8) 0.0050(8) C5 0.0509(15) 0.0371(14) 0.0458(14) -0.0063(11) 0.0122(11) 0.0065(10) C6 0.0499(15) 0.0429(15) 0.049(2) -0.0132(12) 0.0150(11) 0.0047(11) N7 0.0475(12) 0.0512(13) 0.0348(11) -0.0099(9) 0.0105(9) 0.0013(9) C8 0.0432(13) 0.0454(14) 0.0364(13) -0.0037(10) 0.0091(10) 0.0017(10) C9 0.0351(12) 0.0412(13) 0.0353(12) -0.0019(10) 0.0093(9) 0.0037(9) O10 0.0575(11) 0.0524(11) 0.0355(9) 0.0043(8) 0.0107(8) 0.0119(8) C11 0.0336(12) 0.0464(14) 0.0386(13) -0.0105(10) 0.0118(9) -0.0024(9) C12 0.051(2) 0.058(2) 0.0373(13) -0.0105(12) 0.0057(11) 0.0083(12) C13 0.060(2) 0.078(2) 0.0395(15) -0.0178(14) 0.0053(12) 0.0089(15) C14 0.062(2) 0.065(2) 0.056(2) -0.0292(15) 0.0198(14) -0.0062(14) C15 0.071(2) 0.051(2) 0.061(2) -0.0159(14) 0.0289(15) -0.0040(14) C16 0.057(2) 0.048(2) 0.0437(14) -0.0106(12) 0.0193(12) -0.0007(12) O17 0.0647(13) 0.0489(11) 0.0511(12) 0.0032(9) 0.0164(10) 0.0114(9) O18 0.0647(13) 0.099(2) 0.0375(10) -0.0133(11) 0.0159(9) -0.0107(12) _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 C2 1.345(3) . ? N1 C9 1.345(3) . ? C2 C3 1.443(4) . ? C2 C11 1.463(3) . ? C3 O10 1.259(3) . ? C3 N4 1.366(3) . ? N4 C5 1.391(3) . ? N4 C9 1.402(3) . ? C5 C6 1.333(4) . ? C5 H5 1.02(3) . ? C6 N7 1.375(3) . ? C6 H6 0.94(4) . ? N7 C8 1.345(3) . ? N7 H7 0.96(3) . ? C8 C9 1.352(3) . ? C8 H8 0.97(3) . ? C11 C12 1.390(4) . ? C11 C16 1.392(4) . ? C12 C13 1.379(4) . ? C12 H12 0.95(4) . ? C13 C14 1.386(5) . ? C13 H13 0.99(3) . ? C14 C15 1.370(4) . ? C14 H14 0.98(3) . ? C15 C16 1.391(4) . ? C15 H15 1.02(3) . ? C16 H16 1.02(3) . ? O17 H17A 0.93(4) . ? O17 H17B 0.86(4) . ? O18 H18A 0.94(4) . ? O18 H18B 0.89(4) . ? 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 C2 N1 C9 106.6(2) . . ? N1 C2 C3 111.6(2) . . ? N1 C2 C11 121.9(2) . . ? C3 C2 C11 126.6(2) . . ? O10 C3 N4 123.6(2) . . ? O10 C3 C2 133.4(2) . . ? N4 C3 C2 102.9(2) . . ? C3 N4 C5 130.9(2) . . ? C3 N4 C9 109.4(2) . . ? C5 N4 C9 119.7(2) . . ? C6 C5 N4 118.7(2) . . ? C6 C5 H5 126.0(19) . . ? N4 C5 H5 115.3(19) . . ? C5 C6 N7 121.1(2) . . ? C5 C6 H6 117.7(21) . . ? N7 C6 H6 121.2(21) . . ? C8 N7 C6 121.2(2) . . ? C8 N7 H7 115.8(21) . . ? C6 N7 H7 122.7(21) . . ? N7 C8 C9 119.7(2) . . ? N7 C8 H8 118.8(21) . . ? C9 C8 H8 121.4(21) . . ? N1 C9 C8 130.9(2) . . ? N1 C9 N4 109.6(2) . . ? C8 C9 N4 119.5(2) . . ? C12 C11 C16 118.4(2) . . ? C12 C11 C2 121.4(2) . . ? C16 C11 C2 120.2(2) . . ? C13 C12 C11 120.8(3) . . ? C13 C12 H12 119.3(20) . . ? C11 C12 H12 119.9(20) . . ? C12 C13 C14 120.4(3) . . ? C12 C13 H13 119.1(20) . . ? C14 C13 H13 120.3(20) . . ? C15 C14 C13 119.5(3) . . ? C15 C14 H14 122.8(20) . . ? C13 C14 H14 117.6(20) . . ? C14 C15 C16 120.5(3) . . ? C14 C15 H15 123.3(19) . . ? C16 C15 H15 116.2(19) . . ? C15 C16 C11 120.4(3) . . ? C15 C16 H16 121.1(20) . . ? C11 C16 H16 118.4(20) . . ? H17A O17 H17B 109.8(31) . . ? H18A O18 H18B 102.9(30) . . ? 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 C2 C3 -0.4(3) . . . . ? C9 N1 C2 C11 179.8(2) . . . . ? N1 C2 C3 O10 180.0(2) . . . . ? C11 C2 C3 O10 -0.1(4) . . . . ? N1 C2 C3 N4 1.1(3) . . . . ? C11 C2 C3 N4 -179.0(2) . . . . ? O10 C3 N4 C5 0.3(4) . . . . ? C2 C3 N4 C5 179.3(2) . . . . ? O10 C3 N4 C9 179.6(2) . . . . ? C2 C3 N4 C9 -1.4(2) . . . . ? C3 N4 C5 C6 179.0(2) . . . . ? C9 N4 C5 C6 -0.2(3) . . . . ? N4 C5 C6 N7 -1.2(4) . . . . ? C5 C6 N7 C8 2.0(4) . . . . ? C6 N7 C8 C9 -1.3(4) . . . . ? C2 N1 C9 C8 179.2(3) . . . . ? C2 N1 C9 N4 -0.6(2) . . . . ? N7 C8 C9 N1 -179.9(2) . . . . ? N7 C8 C9 N4 -0.1(3) . . . . ? C3 N4 C9 N1 1.3(3) . . . . ? C5 N4 C9 N1 -179.3(2) . . . . ? C3 N4 C9 C8 -178.5(2) . . . . ? C5 N4 C9 C8 0.9(3) . . . . ? N1 C2 C11 C12 -177.3(2) . . . . ? C3 C2 C11 C12 2.9(4) . . . . ? N1 C2 C11 C16 2.6(3) . . . . ? C3 C2 C11 C16 -177.2(2) . . . . ? C16 C11 C12 C13 0.2(4) . . . . ? C2 C11 C12 C13 -180.0(3) . . . . ? C11 C12 C13 C14 0.2(5) . . . . ? C12 C13 C14 C15 -0.4(5) . . . . ? C13 C14 C15 C16 0.2(5) . . . . ? C14 C15 C16 C11 0.1(4) . . . . ? C12 C11 C16 C15 -0.3(4) . . . . ? C2 C11 C16 C15 179.8(2) . . . . ? _refine_diff_density_max 0.249 _refine_diff_density_min -0.259 _refine_diff_density_rms 0.054 data_jm1 _audit_creation_method SHELXL _chemical_name_systematic ; ? ; _chemical_name_common 'compoud 5b' _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C13 H13 N3 O2' _chemical_formula_weight 243.26 _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 monoclinic _symmetry_space_group_name_H-M P21/a loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z' '-x, -y, -z' 'x-1/2, -y-1/2, z' _cell_length_a 12.022(4) _cell_length_b 8.616(2) _cell_length_c 13.244(4) _cell_angle_alpha 90.00 _cell_angle_beta 114.22(3) _cell_angle_gamma 90.00 _cell_volume 1251.1(6) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.292 _exptl_crystal_density_method ? _exptl_crystal_F_000 512 _exptl_absorpt_coefficient_mu 0.090 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoKa _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device ? _diffrn_measurement_method ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 1928 _diffrn_reflns_av_R_equivalents 0.0470 _diffrn_reflns_av_sigmaI/netI 0.1656 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.90 _diffrn_reflns_theta_max 23.50 _reflns_number_total 1858 _reflns_number_observed 749 _reflns_observed_criterion >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement on F^2^ for ALL reflections except for 0 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R- factors wR and all goodnesses of fit S are based on F^2^, conventional R- factors R are based on F, with F set to zero for negative F^2^. The observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme 'calc w=1/[s^2^(Fo^2^)+( 0.0420P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment ? _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1858 _refine_ls_number_parameters 170 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1642 _refine_ls_R_factor_obs 0.0679 _refine_ls_wR_factor_all 0.1249 _refine_ls_wR_factor_obs 0.1054 _refine_ls_goodness_of_fit_all 0.849 _refine_ls_goodness_of_fit_obs 1.217 _refine_ls_restrained_S_all 0.849 _refine_ls_restrained_S_obs 1.217 _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 N1 N 0.4092(3) 0.3933(5) 0.6458(3) 0.0564(11) Uani 1 d . . C2 C 0.4963(4) 0.4849(6) 0.7327(4) 0.0505(13) Uani 1 d . . C3 C 0.4326(4) 0.5908(6) 0.7835(4) 0.0558(13) Uani 1 d . . O4 O 0.3254(3) 0.6199(4) 0.7322(2) 0.0829(12) Uani 1 d . . C5 C 0.5013(5) 0.6549(6) 0.8956(4) 0.0594(14) Uani 1 d . . C6 C 0.4416(5) 0.7462(7) 0.9406(4) 0.089(2) Uani 1 d . . H6 H 0.3599(5) 0.7704(7) 0.9000(4) 0.117(6) Uiso 1 calc R . C7 C 0.5014(8) 0.8025(9) 1.0452(6) 0.132(3) Uani 1 d . . H7 H 0.4596(8) 0.8634(9) 1.0762(6) 0.117(6) Uiso 1 calc R . C8 C 0.6208(9) 0.7709(11) 1.1044(6) 0.138(4) Uani 1 d . . H8 H 0.6602(9) 0.8104(11) 1.1757(6) 0.117(6) Uiso 1 calc R . C9 C 0.6832(7) 0.6832(9) 1.0618(5) 0.119(3) Uani 1 d . . H9 H 0.7655(7) 0.6627(9) 1.1029(5) 0.117(6) Uiso 1 calc R . C10 C 0.6233(5) 0.6232(6) 0.9550(4) 0.084(2) Uani 1 d . . H10 H 0.6654(5) 0.5624(6) 0.9243(4) 0.117(6) Uiso 1 calc R . O11 O 0.5562(3) 0.5944(4) 0.6927(2) 0.0745(10) Uani 1 d . . C12 C 0.6403(4) 0.5308(6) 0.6545(4) 0.089(2) Uani 1 d . . H12A H 0.6765(4) 0.6129(6) 0.6292(4) 0.117(6) Uiso 1 calc R . H12B H 0.5986(4) 0.4604(6) 0.5947(4) 0.117(6) Uiso 1 calc R . H12C H 0.7029(4) 0.4760(6) 0.7139(4) 0.117(6) Uiso 1 calc R . C13 C 0.4237(4) 0.2393(6) 0.6304(3) 0.0457(12) Uani 1 d . . N14 N 0.5292(3) 0.1711(5) 0.6923(3) 0.0600(12) Uani 1 d . . C15 C 0.5364(4) 0.0192(6) 0.6724(4) 0.0628(15) Uani 1 d . . H15 H 0.6085(4) -0.0332(6) 0.7137(4) 0.117(6) Uiso 1 calc R . C16 C 0.4429(5) -0.0615(6) 0.5945(4) 0.0638(15) Uani 1 d . . H16 H 0.4526(5) -0.1668(6) 0.5849(4) 0.117(6) Uiso 1 calc R . N17 N 0.3378(3) 0.0072(5) 0.5319(3) 0.0563(11) Uani 1 d . . C18 C 0.3293(4) 0.1557(5) 0.5507(4) 0.0515(13) Uani 1 d . . H18 H 0.2569(4) 0.2072(5) 0.5088(4) 0.117(6) Uiso 1 calc R . H1 H 0.3358(44) 0.4406(59) 0.6137(41) 0.117(6) Uiso 1 d . . H2 H 0.5628(40) 0.4086(59) 0.7849(37) 0.117(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 N1 0.054(3) 0.050(3) 0.049(3) -0.002(2) 0.005(2) 0.014(2) C2 0.046(3) 0.050(3) 0.051(3) -0.012(3) 0.016(3) -0.004(3) C3 0.052(3) 0.054(3) 0.056(3) -0.005(3) 0.016(3) -0.009(3) O4 0.057(2) 0.102(3) 0.075(2) -0.027(2) 0.012(2) 0.015(2) C5 0.064(3) 0.062(4) 0.054(3) -0.013(3) 0.026(3) -0.012(3) C6 0.112(5) 0.091(4) 0.068(4) -0.033(4) 0.041(4) -0.013(4) C7 0.179(8) 0.134(7) 0.117(7) -0.073(6) 0.095(6) -0.071(7) C8 0.185(10) 0.167(9) 0.069(6) -0.049(6) 0.060(6) -0.114(9) C9 0.105(6) 0.164(8) 0.062(5) -0.015(4) 0.007(4) -0.072(5) C10 0.070(4) 0.108(5) 0.061(4) -0.009(4) 0.015(3) -0.014(4) O11 0.084(2) 0.062(2) 0.095(3) 0.005(2) 0.055(2) -0.001(2) C12 0.082(4) 0.108(5) 0.093(4) 0.018(4) 0.052(3) 0.003(4) C13 0.043(3) 0.049(3) 0.037(3) 0.002(3) 0.008(2) 0.005(3) N14 0.051(3) 0.061(3) 0.051(3) -0.004(2) 0.004(2) 0.016(2) C15 0.058(4) 0.054(4) 0.067(4) 0.000(3) 0.016(3) 0.022(3) C16 0.057(3) 0.054(4) 0.070(4) 0.001(3) 0.016(3) 0.004(3) N17 0.051(3) 0.049(3) 0.058(3) -0.005(2) 0.012(2) -0.003(2) C18 0.051(3) 0.045(3) 0.053(3) -0.002(3) 0.015(3) -0.004(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 N1 C13 1.364(5) . ? N1 C2 1.434(5) . ? N1 H1 0.90(5) . ? C2 O11 1.415(5) . ? C2 C3 1.514(6) . ? C2 H2 1.05(5) . ? C3 O4 1.212(4) . ? C3 C5 1.478(6) . ? C5 C6 1.356(6) . ? C5 C10 1.378(5) . ? C6 C7 1.362(7) . ? C6 H6 0.93 . ? C7 C8 1.351(9) . ? C7 H7 0.93 . ? C8 C9 1.342(9) . ? C8 H8 0.93 . ? C9 C10 1.396(7) . ? C9 H9 0.93 . ? C10 H10 0.93 . ? O11 C12 1.414(5) . ? C12 H12A 0.96 . ? C12 H12B 0.96 . ? C12 H12C 0.96 . ? C13 N14 1.332(5) . ? C13 C18 1.392(5) . ? N14 C15 1.345(5) . ? C15 C16 1.364(5) . ? C15 H15 0.93 . ? C16 N17 1.332(5) . ? C16 H16 0.93 . ? N17 C18 1.316(5) . ? C18 H18 0.93 . ? 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 C13 N1 C2 124.0(4) . . ? C13 N1 H1 121.9(33) . . ? C2 N1 H1 112.3(33) . . ? O11 C2 N1 112.5(4) . . ? O11 C2 C3 101.1(4) . . ? N1 C2 C3 110.6(4) . . ? O11 C2 H2 107.3(26) . . ? N1 C2 H2 107.0(27) . . ? C3 C2 H2 118.3(25) . . ? O4 C3 C5 120.9(5) . . ? O4 C3 C2 119.4(4) . . ? C5 C3 C2 119.7(4) . . ? C6 C5 C10 119.7(5) . . ? C6 C5 C3 118.7(5) . . ? C10 C5 C3 121.6(5) . . ? C5 C6 C7 120.0(6) . . ? C5 C6 H6 120.0(3) . . ? C7 C6 H6 120.0(5) . . ? C8 C7 C6 120.7(8) . . ? C8 C7 H7 119.7(6) . . ? C6 C7 H7 119.7(5) . . ? C9 C8 C7 120.9(9) . . ? C9 C8 H8 119.6(5) . . ? C7 C8 H8 119.6(6) . . ? C8 C9 C10 119.3(8) . . ? C8 C9 H9 120.3(5) . . ? C10 C9 H9 120.3(4) . . ? C5 C10 C9 119.4(6) . . ? C5 C10 H10 120.3(3) . . ? C9 C10 H10 120.3(4) . . ? C12 O11 C2 115.1(4) . . ? O11 C12 H12A 109.5(2) . . ? O11 C12 H12B 109.5(2) . . ? H12A C12 H12B 109.5 . . ? O11 C12 H12C 109.5(2) . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? N14 C13 N1 119.0(4) . . ? N14 C13 C18 120.8(5) . . ? N1 C13 C18 120.1(5) . . ? C13 N14 C15 115.5(4) . . ? N14 C15 C16 123.0(5) . . ? N14 C15 H15 118.5(3) . . ? C16 C15 H15 118.5(3) . . ? N17 C16 C15 121.4(5) . . ? N17 C16 H16 119.3(3) . . ? C15 C16 H16 119.3(3) . . ? C18 N17 C16 116.2(4) . . ? N17 C18 C13 123.0(5) . . ? N17 C18 H18 118.5(3) . . ? C13 C18 H18 118.5(3) . . ? 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 C13 N1 C2 O11 110.1(5) . . . . ? C13 N1 C2 C3 -137.7(4) . . . . ? O11 C2 C3 O4 99.8(5) . . . . ? N1 C2 C3 O4 -19.6(7) . . . . ? O11 C2 C3 C5 -81.3(5) . . . . ? N1 C2 C3 C5 159.3(4) . . . . ? O4 C3 C5 C6 0.6(7) . . . . ? C2 C3 C5 C6 -178.3(5) . . . . ? O4 C3 C5 C10 -179.9(5) . . . . ? C2 C3 C5 C10 1.2(7) . . . . ? C10 C5 C6 C7 -1.8(8) . . . . ? C3 C5 C6 C7 177.7(5) . . . . ? C5 C6 C7 C8 1.3(10) . . . . ? C6 C7 C8 C9 -0.1(13) . . . . ? C7 C8 C9 C10 -0.5(12) . . . . ? C6 C5 C10 C9 1.3(8) . . . . ? C3 C5 C10 C9 -178.3(5) . . . . ? C8 C9 C10 C5 -0.1(9) . . . . ? N1 C2 O11 C12 -71.3(5) . . . . ? C3 C2 O11 C12 170.7(3) . . . . ? C2 N1 C13 N14 -6.6(7) . . . . ? C2 N1 C13 C18 173.7(4) . . . . ? N1 C13 N14 C15 179.9(4) . . . . ? C18 C13 N14 C15 -0.4(6) . . . . ? C13 N14 C15 C16 -0.1(7) . . . . ? N14 C15 C16 N17 0.8(8) . . . . ? C15 C16 N17 C18 -0.9(7) . . . . ? C16 N17 C18 C13 0.4(7) . . . . ? N14 C13 C18 N17 0.2(7) . . . . ? N1 C13 C18 N17 179.9(4) . . . . ? _refine_diff_density_max 0.140 _refine_diff_density_min -0.138 _refine_diff_density_rms 0.037