# Supplementary Material (ESI) for New Journal of Chemistry # This journal is (c) The Royal Society of Chemistry and # The Centre National de la Recherche Scientifique, 2007 data_global _journal_coden_Cambridge 440 loop_ _publ_author_name P.Simunek V.Bertolasi A.Lycka V.Machacek L.Pretto M.Svobodova _publ_contact_author_name 'Petr Simunek' _publ_contact_author_address ; Organic Chemistry University of Pardubice Nam. Cs. Legii 565 Pardubice CZ 532 10 CZECH REPUBLIC ; _publ_contact_author_email PETR.SIMUNEK@UPCE.CZ _publ_requested_journal 'New Journal of Chemistry' _publ_section_title ; Structure and Tautomerism of Azo Coupling Products from N-Alkylenaminones Derived from Acetylacetone and Benzoylacetone in Solid Phase and in Solution ; data_(1) _database_code_depnum_ccdc_archive 'CCDC 633157' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C13 H17 N3 O' _chemical_formula_sum 'C13 H17 N3 O' _chemical_formula_weight 231.30 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 'P 21/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 6.6026(1) _cell_length_b 12.9320(2) _cell_length_c 15.1197(3) _cell_angle_alpha 90.00 _cell_angle_beta 102.1089(9) _cell_angle_gamma 90.00 _cell_volume 1262.27(4) _cell_formula_units_Z 4 _cell_measurement_temperature 150 _cell_measurement_reflns_used 3779 _cell_measurement_theta_min 3.5 _cell_measurement_theta_max 28.0 _exptl_crystal_description prismatic _exptl_crystal_colour yellow _exptl_crystal_size_max 0.39 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.217 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 496 _exptl_absorpt_coefficient_mu 0.080 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 150 _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_measurement_method '\f scans and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 24933 _diffrn_reflns_av_R_equivalents 0.033 _diffrn_reflns_av_sigmaI/netI 0.0227 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 3.5 _diffrn_reflns_theta_max 28.0 _reflns_number_total 3027 _reflns_number_gt 2594 _reflns_threshold_expression I>2sigma(I) _computing_data_collection 'COLLECT (Nonius, 1997)' _computing_cell_refinement 'Denzo SMN (Otwinowski & Minor, 1997)' _computing_data_reduction 'Denzo SMN (Otwinowski & Minor, 1997)' _computing_structure_solution 'SIR97 (Altomare et al., 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEPIII (Burnett & Johnson, 1996)' _computing_publication_material ; SHELXL-97 (Sheldrick, 1997), PARST (Nardelli, 1995) ; _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^)+(0.0672P)^2^+0.2378P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3027 _refine_ls_number_parameters 225 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0491 _refine_ls_R_factor_gt 0.0421 _refine_ls_wR_factor_ref 0.1211 _refine_ls_wR_factor_gt 0.1146 _refine_ls_goodness_of_fit_ref 1.070 _refine_ls_restrained_S_all 1.070 _refine_ls_shift/su_max 0.000 _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 -0.05409(17) 0.18906(9) 1.01241(6) 0.0560(3) Uani 1 1 d . . . N1 N 0.20772(14) 0.17567(7) 0.75078(6) 0.0262(2) Uani 1 1 d . . . H1 H 0.102(16) 0.199(8) 0.707(7) 0.031 Uiso 0.13(2) 1 d P . . N2 N 0.20436(13) 0.15458(7) 0.83348(6) 0.0257(2) Uani 1 1 d . . . N3 N -0.11482(14) 0.28912(7) 0.74122(6) 0.0282(2) Uani 1 1 d . . . H3 H -0.014(3) 0.2591(13) 0.7169(11) 0.034 Uiso 0.87(2) 1 d P . . C1 C 0.05046(16) 0.19627(8) 0.87137(7) 0.0264(2) Uani 1 1 d . . . C2 C -0.10885(16) 0.26447(8) 0.82618(7) 0.0264(2) Uani 1 1 d . . . C3 C 0.06633(18) 0.16230(9) 0.96500(7) 0.0332(3) Uani 1 1 d . . . C4 C -0.26879(19) 0.31066(10) 0.87175(9) 0.0346(3) Uani 1 1 d . . . C5 C 0.2419(2) 0.09071(12) 1.00580(9) 0.0447(3) Uani 1 1 d . . . C6 C 0.37464(15) 0.12956(8) 0.71913(7) 0.0244(2) Uani 1 1 d . . . C7 C 0.37206(17) 0.14286(9) 0.62754(7) 0.0295(2) Uani 1 1 d . . . C8 C 0.52897(17) 0.10153(9) 0.58998(7) 0.0306(2) Uani 1 1 d . . . C9 C 0.69094(16) 0.04579(8) 0.64245(7) 0.0283(2) Uani 1 1 d . . . C10 C 0.69135(16) 0.03258(8) 0.73410(7) 0.0282(2) Uani 1 1 d . . . C11 C 0.53657(15) 0.07418(8) 0.77284(7) 0.0257(2) Uani 1 1 d . . . C12 C -0.26492(19) 0.35728(10) 0.68509(9) 0.0358(3) Uani 1 1 d . . . C13 C 0.86133(19) 0.00108(12) 0.60179(9) 0.0408(3) Uani 1 1 d . . . H41 H -0.201(3) 0.3334(15) 0.9323(14) 0.069(5) Uiso 1 1 d . . . H42 H -0.361(4) 0.2618(18) 0.8857(14) 0.088(7) Uiso 1 1 d . . . H43 H -0.332(4) 0.371(2) 0.8428(16) 0.092(7) Uiso 1 1 d . . . H51 H 0.237(3) 0.0831(14) 1.0673(12) 0.057(5) Uiso 1 1 d . . . H52 H 0.377(3) 0.1208(14) 1.0002(12) 0.059(5) Uiso 1 1 d . . . H53 H 0.220(3) 0.0228(15) 0.9737(13) 0.066(5) Uiso 1 1 d . . . H7 H 0.260(2) 0.1807(12) 0.5910(10) 0.044(4) Uiso 1 1 d . . . H8 H 0.526(2) 0.1115(12) 0.5253(11) 0.045(4) Uiso 1 1 d . . . H10 H 0.806(2) -0.0075(12) 0.7737(10) 0.041(4) Uiso 1 1 d . . . H11 H 0.542(2) 0.0664(11) 0.8379(10) 0.035(3) Uiso 1 1 d . . . H121 H -0.404(2) 0.3404(13) 0.6890(10) 0.048(4) Uiso 1 1 d . . . H122 H -0.245(3) 0.4301(15) 0.7052(11) 0.059(5) Uiso 1 1 d . . . H123 H -0.243(3) 0.3509(14) 0.6231(12) 0.056(5) Uiso 1 1 d . . . H131 H 0.844(4) -0.080(2) 0.5940(16) 0.100(7) Uiso 1 1 d . . . H132 H 0.988(3) 0.0003(17) 0.6431(14) 0.075(6) Uiso 1 1 d . . . H133 H 0.863(4) 0.0230(19) 0.5443(17) 0.094(7) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0627(6) 0.0771(8) 0.0365(5) 0.0084(5) 0.0293(5) 0.0151(5) N1 0.0284(4) 0.0268(4) 0.0258(4) -0.0005(3) 0.0108(3) 0.0024(3) N2 0.0280(4) 0.0257(4) 0.0247(4) -0.0024(3) 0.0088(3) -0.0030(3) N3 0.0302(4) 0.0268(4) 0.0299(5) -0.0012(3) 0.0116(4) 0.0044(4) C1 0.0286(5) 0.0271(5) 0.0255(5) -0.0047(4) 0.0103(4) -0.0031(4) C2 0.0286(5) 0.0236(5) 0.0292(5) -0.0066(4) 0.0114(4) -0.0043(4) C3 0.0396(6) 0.0361(6) 0.0262(5) -0.0038(4) 0.0123(4) -0.0054(5) C4 0.0352(6) 0.0361(6) 0.0370(6) -0.0067(5) 0.0179(5) 0.0017(5) C5 0.0554(8) 0.0518(8) 0.0267(6) 0.0052(5) 0.0079(5) 0.0066(6) C6 0.0256(5) 0.0221(5) 0.0274(5) -0.0006(4) 0.0100(4) -0.0005(4) C7 0.0305(5) 0.0312(5) 0.0284(5) 0.0050(4) 0.0101(4) 0.0057(4) C8 0.0331(5) 0.0341(6) 0.0275(5) 0.0030(4) 0.0130(4) 0.0031(4) C9 0.0258(5) 0.0280(5) 0.0338(5) -0.0023(4) 0.0127(4) -0.0002(4) C10 0.0252(5) 0.0276(5) 0.0321(5) 0.0006(4) 0.0067(4) 0.0012(4) C11 0.0270(5) 0.0247(5) 0.0262(5) -0.0001(4) 0.0076(4) -0.0018(4) C12 0.0381(6) 0.0338(6) 0.0373(6) 0.0021(5) 0.0118(5) 0.0098(5) C13 0.0324(6) 0.0530(8) 0.0404(7) -0.0016(6) 0.0153(5) 0.0115(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C3 1.2267(14) . ? N1 N2 1.2845(12) . ? N1 C6 1.4214(13) . ? N1 H1 0.91(11) . ? N2 C1 1.3769(13) . ? N3 C2 1.3162(14) . ? N3 C12 1.4583(14) . ? N3 H3 0.914(18) . ? C1 C2 1.4316(15) . ? C1 C3 1.4649(15) . ? C2 C4 1.5006(14) . ? C3 C5 1.5105(18) . ? C4 H41 0.98(2) . ? C4 H42 0.93(2) . ? C4 H43 0.95(3) . ? C5 H51 0.943(18) . ? C5 H52 0.993(18) . ? C5 H53 1.00(2) . ? C6 C7 1.3920(14) . ? C6 C11 1.3969(14) . ? C7 C8 1.3887(15) . ? C7 H7 0.960(16) . ? C8 C9 1.3917(15) . ? C8 H8 0.982(16) . ? C9 C10 1.3957(15) . ? C9 C13 1.5061(14) . ? C10 C11 1.3885(14) . ? C10 H10 1.005(15) . ? C11 H11 0.983(14) . ? C12 H121 0.958(16) . ? C12 H122 0.990(19) . ? C12 H123 0.982(18) . ? C13 H131 1.06(3) . ? C13 H132 0.93(2) . ? C13 H133 0.92(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N2 N1 C6 114.30(9) . . ? N2 N1 H1 128(6) . . ? C6 N1 H1 116(6) . . ? N1 N2 C1 119.13(9) . . ? C2 N3 C12 126.30(9) . . ? C2 N3 H3 114.5(10) . . ? C12 N3 H3 119.2(10) . . ? N2 C1 C2 125.11(9) . . ? N2 C1 C3 112.04(9) . . ? C2 C1 C3 122.85(9) . . ? N3 C2 C1 118.92(9) . . ? N3 C2 C4 118.15(10) . . ? C1 C2 C4 122.92(9) . . ? O1 C3 C1 123.80(11) . . ? O1 C3 C5 118.05(11) . . ? C1 C3 C5 118.14(10) . . ? C2 C4 H41 108.7(11) . . ? C2 C4 H42 113.0(14) . . ? H41 C4 H42 100.8(17) . . ? C2 C4 H43 113.6(14) . . ? H41 C4 H43 104.8(18) . . ? H42 C4 H43 114.6(19) . . ? C3 C5 H51 106.4(11) . . ? C3 C5 H52 110.6(10) . . ? H51 C5 H52 110.2(14) . . ? C3 C5 H53 108.8(11) . . ? H51 C5 H53 110.8(15) . . ? H52 C5 H53 110.0(14) . . ? C7 C6 C11 119.33(9) . . ? C7 C6 N1 115.75(9) . . ? C11 C6 N1 124.91(9) . . ? C8 C7 C6 120.32(10) . . ? C8 C7 H7 120.8(9) . . ? C6 C7 H7 118.8(9) . . ? C7 C8 C9 121.08(10) . . ? C7 C8 H8 119.7(9) . . ? C9 C8 H8 119.2(9) . . ? C8 C9 C10 118.08(9) . . ? C8 C9 C13 121.10(10) . . ? C10 C9 C13 120.82(10) . . ? C11 C10 C9 121.54(10) . . ? C11 C10 H10 118.5(9) . . ? C9 C10 H10 120.0(9) . . ? C10 C11 C6 119.65(9) . . ? C10 C11 H11 120.5(8) . . ? C6 C11 H11 119.8(8) . . ? N3 C12 H121 111.7(10) . . ? N3 C12 H122 111.4(10) . . ? H121 C12 H122 105.4(14) . . ? N3 C12 H123 106.6(10) . . ? H121 C12 H123 112.1(13) . . ? H122 C12 H123 109.7(14) . . ? C9 C13 H131 110.5(13) . . ? C9 C13 H132 111.9(12) . . ? H131 C13 H132 97.2(18) . . ? C9 C13 H133 115.3(15) . . ? H131 C13 H133 103.0(19) . . ? H132 C13 H133 116.7(19) . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.99 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.225 _refine_diff_density_min -0.219 _refine_diff_density_rms 0.039 ###END=== data_(2) _database_code_depnum_ccdc_archive 'CCDC 633158' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C12 H14 N4 O3' _chemical_formula_sum 'C12 H14 N4 O3' _chemical_formula_weight 262.27 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 'P 21/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 10.2904(2) _cell_length_b 8.7167(2) _cell_length_c 14.0155(3) _cell_angle_alpha 90.00 _cell_angle_beta 100.9315(9) _cell_angle_gamma 90.00 _cell_volume 1234.35(5) _cell_formula_units_Z 4 _cell_measurement_temperature 150 _cell_measurement_reflns_used 3759 _cell_measurement_theta_min 2.0 _cell_measurement_theta_max 28.0 _exptl_crystal_description irregular _exptl_crystal_colour red _exptl_crystal_size_max 0.48 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.19 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.411 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 552 _exptl_absorpt_coefficient_mu 0.105 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 150 _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_measurement_method '\f scans and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 24180 _diffrn_reflns_av_R_equivalents 0.0310 _diffrn_reflns_av_sigmaI/netI 0.0236 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.0 _diffrn_reflns_theta_max 28.0 _reflns_number_total 2976 _reflns_number_gt 2556 _reflns_threshold_expression I>2sigma(I) _computing_data_collection 'COLLECT (Nonius, 1997)' _computing_cell_refinement 'Denzo SMN (Otwinowski & Minor, 1997)' _computing_data_reduction 'Denzo SMN (Otwinowski & Minor, 1997)' _computing_structure_solution 'SIR97 (Altomare et al., 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEPIII (Burnett & Johnson, 1997)' _computing_publication_material ; SHELXL-97 (Sheldrick, 1997), PARST (Nardelli, 1995) ; _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^)+(0.0656P)^2^+0.2684P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2976 _refine_ls_number_parameters 231 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0466 _refine_ls_R_factor_gt 0.0396 _refine_ls_wR_factor_ref 0.1169 _refine_ls_wR_factor_gt 0.1107 _refine_ls_goodness_of_fit_ref 1.078 _refine_ls_restrained_S_all 1.078 _refine_ls_shift/su_max 0.000 _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 0.41470(9) 0.33492(11) 0.26151(6) 0.0388(2) Uani 1 1 d . . . O2 O -0.14270(10) -0.43311(11) 0.53272(8) 0.0438(3) Uani 1 1 d . . . O3 O -0.06157(11) -0.40646(13) 0.68569(8) 0.0511(3) Uani 1 1 d . . . N1 N 0.29796(10) 0.06688(11) 0.51741(7) 0.0239(2) Uani 1 1 d . . . H1 H 0.342(11) 0.086(13) 0.562(9) 0.029 Uiso 0.14(2) 1 d P . . N2 N 0.29432(9) 0.09777(11) 0.42666(6) 0.0239(2) Uani 1 1 d . . . N3 N 0.50769(10) 0.23486(11) 0.56212(7) 0.0255(2) Uani 1 1 d . . . H3 H 0.4460(18) 0.179(2) 0.5813(12) 0.031 Uiso 0.86(2) 1 d P . . N4 N -0.06574(10) -0.37281(12) 0.60004(8) 0.0336(2) Uani 1 1 d . . . C1 C 0.38448(11) 0.19739(12) 0.40221(8) 0.0242(2) Uani 1 1 d . . . C2 C 0.49389(11) 0.26356(12) 0.46839(8) 0.0243(2) Uani 1 1 d . . . C3 C 0.35953(11) 0.23044(14) 0.29735(8) 0.0278(3) Uani 1 1 d . . . C4 C 0.59620(13) 0.36125(16) 0.43491(10) 0.0325(3) Uani 1 1 d . . . C5 C 0.25984(15) 0.13214(18) 0.23114(9) 0.0392(3) Uani 1 1 d . . . C6 C 0.20115(11) -0.04071(12) 0.53247(7) 0.0228(2) Uani 1 1 d . . . C7 C 0.19491(11) -0.07137(13) 0.62960(8) 0.0259(2) Uani 1 1 d . . . C8 C 0.10695(12) -0.17911(14) 0.65246(8) 0.0277(2) Uani 1 1 d . . . C9 C 0.02562(11) -0.25592(12) 0.57719(8) 0.0267(2) Uani 1 1 d . . . C10 C 0.02764(11) -0.22500(13) 0.48011(8) 0.0274(2) Uani 1 1 d . . . C11 C 0.11496(11) -0.11675(13) 0.45776(8) 0.0254(2) Uani 1 1 d . . . C12 C 0.61647(12) 0.28738(17) 0.63732(9) 0.0327(3) Uani 1 1 d . . . H41 H 0.615(2) 0.322(3) 0.3734(16) 0.073(6) Uiso 1 1 d . . . H42 H 0.564(2) 0.462(3) 0.4207(16) 0.076(6) Uiso 1 1 d . . . H43 H 0.684(2) 0.349(3) 0.4781(17) 0.079(7) Uiso 1 1 d . . . H51 H 0.2569(16) 0.162(2) 0.1642(13) 0.045(4) Uiso 1 1 d . . . H52 H 0.171(2) 0.147(2) 0.2459(14) 0.064(6) Uiso 1 1 d . . . H53 H 0.281(2) 0.026(3) 0.2400(15) 0.072(6) Uiso 1 1 d . . . H7 H 0.2519(15) -0.0150(17) 0.6790(11) 0.032(4) Uiso 1 1 d . . . H8 H 0.0996(16) -0.1990(18) 0.7175(12) 0.041(4) Uiso 1 1 d . . . H10 H -0.0304(17) -0.2789(19) 0.4293(12) 0.042(4) Uiso 1 1 d . . . H11 H 0.1158(14) -0.0943(17) 0.3905(10) 0.030(3) Uiso 1 1 d . . . H121 H 0.698(2) 0.246(3) 0.6292(16) 0.082(7) Uiso 1 1 d . . . H122 H 0.604(2) 0.250(3) 0.6991(19) 0.088(7) Uiso 1 1 d . . . H123 H 0.619(3) 0.394(3) 0.6435(18) 0.094(8) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0404(5) 0.0458(5) 0.0301(4) 0.0122(4) 0.0067(4) -0.0009(4) O2 0.0380(5) 0.0350(5) 0.0568(6) -0.0052(4) 0.0049(4) -0.0109(4) O3 0.0558(7) 0.0496(6) 0.0491(6) 0.0146(5) 0.0131(5) -0.0139(5) N1 0.0268(5) 0.0238(5) 0.0204(4) -0.0002(3) 0.0029(4) 0.0011(4) N2 0.0267(5) 0.0236(4) 0.0211(4) 0.0007(3) 0.0035(3) 0.0041(3) N3 0.0250(5) 0.0276(5) 0.0230(4) -0.0021(4) 0.0026(4) 0.0010(4) N4 0.0316(5) 0.0252(5) 0.0446(6) 0.0038(4) 0.0086(4) 0.0005(4) C1 0.0253(5) 0.0248(5) 0.0224(5) 0.0009(4) 0.0040(4) 0.0040(4) C2 0.0246(5) 0.0224(5) 0.0257(5) -0.0001(4) 0.0047(4) 0.0058(4) C3 0.0280(6) 0.0317(6) 0.0239(5) 0.0029(4) 0.0057(4) 0.0077(4) C4 0.0297(6) 0.0352(6) 0.0327(6) 0.0044(5) 0.0063(5) -0.0022(5) C5 0.0472(8) 0.0466(8) 0.0217(6) -0.0004(5) 0.0017(5) -0.0018(6) C6 0.0244(5) 0.0205(5) 0.0227(5) -0.0005(4) 0.0025(4) 0.0038(4) C7 0.0294(6) 0.0244(5) 0.0225(5) -0.0005(4) 0.0010(4) 0.0008(4) C8 0.0314(6) 0.0272(5) 0.0243(5) 0.0026(4) 0.0048(4) 0.0029(4) C9 0.0251(5) 0.0210(5) 0.0337(6) 0.0018(4) 0.0048(4) 0.0014(4) C10 0.0273(5) 0.0244(5) 0.0286(6) -0.0041(4) 0.0003(4) 0.0015(4) C11 0.0284(5) 0.0251(5) 0.0218(5) -0.0021(4) 0.0026(4) 0.0029(4) C12 0.0276(6) 0.0409(7) 0.0275(6) -0.0044(5) -0.0003(5) 0.0007(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C3 1.2297(15) . ? O2 N4 1.2290(15) . ? O3 N4 1.2285(15) . ? N1 N2 1.2937(13) . ? N1 C6 1.4129(14) . ? N1 H1 0.72(12) . ? N2 C1 1.3612(14) . ? N3 C2 1.3182(14) . ? N3 C12 1.4581(15) . ? N3 H3 0.880(19) . ? N4 C9 1.4624(15) . ? C1 C2 1.4369(15) . ? C1 C3 1.4716(15) . ? C2 C4 1.4970(16) . ? C3 C5 1.5121(18) . ? C4 H41 0.98(2) . ? C4 H42 0.95(2) . ? C4 H43 0.99(2) . ? C5 H51 0.969(17) . ? C5 H52 0.98(2) . ? C5 H53 0.95(2) . ? C6 C7 1.4007(15) . ? C6 C11 1.4036(15) . ? C7 C8 1.3834(16) . ? C7 H7 0.954(15) . ? C8 C9 1.3881(16) . ? C8 H8 0.945(16) . ? C9 C10 1.3911(16) . ? C10 C11 1.3794(16) . ? C10 H10 0.961(17) . ? C11 H11 0.964(14) . ? C12 H121 0.94(3) . ? C12 H122 0.96(3) . ? C12 H123 0.93(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N2 N1 C6 113.28(9) . . ? N2 N1 H1 135(9) . . ? C6 N1 H1 112(9) . . ? N1 N2 C1 119.10(9) . . ? C2 N3 C12 125.70(11) . . ? C2 N3 H3 117.5(11) . . ? C12 N3 H3 116.8(11) . . ? O3 N4 O2 123.10(11) . . ? O3 N4 C9 118.39(11) . . ? O2 N4 C9 118.51(11) . . ? N2 C1 C2 125.56(10) . . ? N2 C1 C3 112.22(9) . . ? C2 C1 C3 122.21(10) . . ? N3 C2 C1 119.36(10) . . ? N3 C2 C4 118.11(10) . . ? C1 C2 C4 122.51(10) . . ? O1 C3 C1 123.11(11) . . ? O1 C3 C5 118.75(11) . . ? C1 C3 C5 118.13(11) . . ? C2 C4 H41 110.0(13) . . ? C2 C4 H42 111.1(14) . . ? H41 C4 H42 105.0(17) . . ? C2 C4 H43 111.3(13) . . ? H41 C4 H43 101.0(17) . . ? H42 C4 H43 117.7(19) . . ? C3 C5 H51 109.5(10) . . ? C3 C5 H52 110.1(12) . . ? H51 C5 H52 107.9(15) . . ? C3 C5 H53 110.8(13) . . ? H51 C5 H53 110.7(15) . . ? H52 C5 H53 107.8(17) . . ? C7 C6 C11 119.74(10) . . ? C7 C6 N1 115.81(10) . . ? C11 C6 N1 124.45(10) . . ? C8 C7 C6 120.48(10) . . ? C8 C7 H7 121.3(9) . . ? C6 C7 H7 118.2(9) . . ? C7 C8 C9 118.56(10) . . ? C7 C8 H8 121.6(10) . . ? C9 C8 H8 119.8(10) . . ? C8 C9 C10 122.09(11) . . ? C8 C9 N4 119.32(10) . . ? C10 C9 N4 118.59(10) . . ? C11 C10 C9 119.07(10) . . ? C11 C10 H10 120.4(10) . . ? C9 C10 H10 120.5(10) . . ? C10 C11 C6 120.02(10) . . ? C10 C11 H11 119.2(9) . . ? C6 C11 H11 120.8(9) . . ? N3 C12 H121 111.8(14) . . ? N3 C12 H122 109.5(15) . . ? H121 C12 H122 104.3(19) . . ? N3 C12 H123 112.5(16) . . ? H121 C12 H123 113(2) . . ? H122 C12 H123 105(2) . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 28.00 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.244 _refine_diff_density_min -0.251 _refine_diff_density_rms 0.042 ###END=== data_(3) _database_code_depnum_ccdc_archive 'CCDC 633159' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C13 H17 N3 O2' _chemical_formula_sum 'C13 H17 N3 O2' _chemical_formula_weight 247.30 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 'P 21/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 6.9786(2) _cell_length_b 14.2655(5) _cell_length_c 13.2947(6) _cell_angle_alpha 90.00 _cell_angle_beta 101.364(1) _cell_angle_gamma 90.00 _cell_volume 1297.58(8) _cell_formula_units_Z 4 _cell_measurement_temperature 150 _cell_measurement_reflns_used 2800 _cell_measurement_theta_min 3.3 _cell_measurement_theta_max 28.0 _exptl_crystal_description prismatic _exptl_crystal_colour yellow _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.29 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.266 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 528 _exptl_absorpt_coefficient_mu 0.088 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 150 _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_measurement_method '\f scans and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10831 _diffrn_reflns_av_R_equivalents 0.0290 _diffrn_reflns_av_sigmaI/netI 0.0370 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 3.3 _diffrn_reflns_theta_max 28.0 _reflns_number_total 3058 _reflns_number_gt 2368 _reflns_threshold_expression I>2sigma(I) _computing_data_collection 'COLLECT (Nonius, 1997)' _computing_cell_refinement 'Denzo SMN (Otwinowski & Minor, 1997)' _computing_data_reduction 'Denzo SMN (Otwinowski & Minor, 1997)' _computing_structure_solution 'SIR97 (Altomare et al., 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEPIII (Burnett & Johnson, 1996)' _computing_publication_material ; SHELXL-97 (Sheldrick, 1997), PARST (Nardelli, 1995) ; _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^)+(0.0606P)^2^+0.3502P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3058 _refine_ls_number_parameters 234 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0625 _refine_ls_R_factor_gt 0.0454 _refine_ls_wR_factor_ref 0.1256 _refine_ls_wR_factor_gt 0.1151 _refine_ls_goodness_of_fit_ref 1.028 _refine_ls_restrained_S_all 1.028 _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 O1 O 0.2329(2) -0.21318(9) 0.08075(10) 0.0710(5) Uani 1 1 d . . . O2 O 0.18221(15) 0.45774(7) 0.13551(8) 0.0386(3) Uani 1 1 d . . . N1 N 0.26522(15) 0.07888(8) 0.23776(9) 0.0278(3) Uani 1 1 d . . . H1 H 0.329(18) 0.063(9) 0.303(10) 0.033 Uiso 0.13(2) 1 d P . . N2 N 0.25136(15) 0.02179(8) 0.16155(9) 0.0287(3) Uani 1 1 d . . . N3 N 0.30040(16) -0.06325(9) 0.35953(9) 0.0310(3) Uani 1 1 d . . . H3 H 0.301(3) -0.0018(16) 0.3489(14) 0.037 Uiso 0.87(2) 1 d P . . C1 C 0.25865(18) -0.07308(9) 0.17892(11) 0.0302(3) Uani 1 1 d . . . C2 C 0.27818(17) -0.11667(9) 0.27722(11) 0.0296(3) Uani 1 1 d . . . C3 C 0.2449(2) -0.12765(11) 0.08417(12) 0.0407(4) Uani 1 1 d . . . C4 C 0.2757(2) -0.22059(10) 0.29231(14) 0.0378(4) Uani 1 1 d . . . C5 C 0.2461(3) -0.07483(15) -0.01477(13) 0.0492(4) Uani 1 1 d . . . C6 C 0.24513(17) 0.17477(9) 0.20857(10) 0.0260(3) Uani 1 1 d . . . C7 C 0.26705(18) 0.24028(10) 0.28736(10) 0.0284(3) Uani 1 1 d . . . C8 C 0.24841(19) 0.33579(10) 0.26716(11) 0.0297(3) Uani 1 1 d . . . C9 C 0.20556(18) 0.36617(9) 0.16585(10) 0.0291(3) Uani 1 1 d . . . C10 C 0.1822(2) 0.30092(10) 0.08621(11) 0.0318(3) Uani 1 1 d . . . C11 C 0.20205(19) 0.20635(10) 0.10681(11) 0.0298(3) Uani 1 1 d . . . C12 C 0.3243(3) -0.09581(12) 0.46505(12) 0.0398(4) Uani 1 1 d . . . C13 C 0.2051(2) 0.52782(11) 0.21361(13) 0.0392(4) Uani 1 1 d . . . H41 H 0.357(3) -0.2531(17) 0.2572(18) 0.082(7) Uiso 1 1 d . . . H42 H 0.157(3) -0.2445(16) 0.2750(16) 0.075(7) Uiso 1 1 d . . . H43 H 0.319(4) -0.236(2) 0.359(3) 0.130(11) Uiso 1 1 d . . . H51 H 0.346(4) -0.033(2) -0.014(2) 0.108(9) Uiso 1 1 d . . . H52 H 0.224(4) -0.117(2) -0.072(2) 0.124(10) Uiso 1 1 d . . . H53 H 0.125(5) -0.035(2) -0.035(2) 0.129(11) Uiso 1 1 d . . . H7 H 0.298(2) 0.2198(12) 0.3567(13) 0.035(4) Uiso 1 1 d . . . H8 H 0.263(2) 0.3806(12) 0.3228(12) 0.037(4) Uiso 1 1 d . . . H10 H 0.147(2) 0.3231(11) 0.0147(13) 0.041(4) Uiso 1 1 d . . . H11 H 0.185(2) 0.1614(11) 0.0526(12) 0.034(4) Uiso 1 1 d . . . H121 H 0.222(3) -0.1424(15) 0.4728(16) 0.066(6) Uiso 1 1 d . . . H122 H 0.451(3) -0.1246(14) 0.4882(15) 0.062(5) Uiso 1 1 d . . . H123 H 0.313(3) -0.0407(14) 0.5067(15) 0.056(5) Uiso 1 1 d . . . H131 H 0.179(2) 0.5856(13) 0.1748(13) 0.047(5) Uiso 1 1 d . . . H132 H 0.341(3) 0.5271(12) 0.2559(13) 0.043(4) Uiso 1 1 d . . . H133 H 0.110(2) 0.5192(12) 0.2579(13) 0.047(5) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.1144(12) 0.0348(7) 0.0515(8) -0.0170(6) -0.0137(7) 0.0145(7) O2 0.0522(6) 0.0236(5) 0.0416(6) 0.0025(4) 0.0129(5) -0.0014(4) N1 0.0273(5) 0.0234(6) 0.0321(6) -0.0020(5) 0.0045(4) -0.0012(4) N2 0.0241(5) 0.0275(6) 0.0339(6) -0.0044(5) 0.0040(4) 0.0001(4) N3 0.0356(6) 0.0221(6) 0.0352(6) -0.0002(5) 0.0066(5) 0.0004(5) C1 0.0250(6) 0.0254(7) 0.0382(7) -0.0058(5) 0.0010(5) 0.0020(5) C2 0.0215(6) 0.0239(7) 0.0424(8) -0.0032(6) 0.0039(5) 0.0012(5) C3 0.0378(7) 0.0361(8) 0.0428(8) -0.0121(7) -0.0051(6) 0.0066(6) C4 0.0370(8) 0.0233(7) 0.0532(10) -0.0047(7) 0.0095(7) -0.0006(6) C5 0.0549(10) 0.0536(11) 0.0388(9) -0.0154(8) 0.0082(7) -0.0073(9) C6 0.0226(6) 0.0247(6) 0.0313(7) -0.0008(5) 0.0064(5) -0.0020(5) C7 0.0294(6) 0.0277(7) 0.0286(7) -0.0006(5) 0.0069(5) -0.0024(5) C8 0.0303(6) 0.0282(7) 0.0316(7) -0.0048(6) 0.0084(5) -0.0031(5) C9 0.0281(6) 0.0238(6) 0.0371(7) 0.0016(5) 0.0106(5) -0.0026(5) C10 0.0355(7) 0.0310(7) 0.0297(7) 0.0022(6) 0.0085(5) -0.0015(5) C11 0.0313(6) 0.0287(7) 0.0297(7) -0.0046(6) 0.0068(5) -0.0032(5) C12 0.0511(9) 0.0314(8) 0.0378(8) 0.0036(7) 0.0109(7) -0.0004(7) C13 0.0413(8) 0.0267(8) 0.0509(9) -0.0043(7) 0.0119(7) 0.0005(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C3 1.223(2) . ? O2 C9 1.3674(16) . ? O2 C13 1.4275(18) . ? N1 N2 1.2886(16) . ? N1 C6 1.4213(17) . ? N1 H1 0.92(13) . ? N2 C1 1.3723(17) . ? N3 C2 1.3173(18) . ? N3 C12 1.4558(19) . ? N3 H3 0.89(2) . ? C1 C2 1.429(2) . ? C1 C3 1.4678(19) . ? C2 C4 1.4965(19) . ? C3 C5 1.517(2) . ? C4 H41 0.93(2) . ? C4 H42 0.89(2) . ? C4 H43 0.91(3) . ? C5 H51 0.92(3) . ? C5 H52 0.96(3) . ? C5 H53 1.01(3) . ? C6 C7 1.3896(18) . ? C6 C11 1.4011(19) . ? C7 C8 1.3898(19) . ? C7 H7 0.951(16) . ? C8 C9 1.390(2) . ? C8 H8 0.967(17) . ? C9 C10 1.3951(19) . ? C10 C11 1.378(2) . ? C10 H10 0.985(17) . ? C11 H11 0.955(16) . ? C12 H121 1.00(2) . ? C12 H122 0.97(2) . ? C12 H123 0.97(2) . ? C13 H131 0.970(19) . ? C13 H132 1.005(17) . ? C13 H133 0.978(18) . ? 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 C9 O2 C13 117.69(12) . . ? N2 N1 C6 113.92(11) . . ? N2 N1 H1 122(8) . . ? C6 N1 H1 120(8) . . ? N1 N2 C1 119.77(12) . . ? C2 N3 C12 126.03(13) . . ? C2 N3 H3 116.2(12) . . ? C12 N3 H3 117.7(12) . . ? N2 C1 C2 125.21(12) . . ? N2 C1 C3 112.62(13) . . ? C2 C1 C3 122.16(13) . . ? N3 C2 C1 118.83(12) . . ? N3 C2 C4 117.67(13) . . ? C1 C2 C4 123.50(13) . . ? O1 C3 C1 123.60(16) . . ? O1 C3 C5 118.36(15) . . ? C1 C3 C5 118.04(14) . . ? C2 C4 H41 113.9(14) . . ? C2 C4 H42 112.4(14) . . ? H41 C4 H42 108(2) . . ? C2 C4 H43 111(2) . . ? H41 C4 H43 105(2) . . ? H42 C4 H43 106(2) . . ? C3 C5 H51 116.4(17) . . ? C3 C5 H52 110.4(18) . . ? H51 C5 H52 115(2) . . ? C3 C5 H53 111.6(17) . . ? H51 C5 H53 103(2) . . ? H52 C5 H53 98(2) . . ? C7 C6 C11 118.84(12) . . ? C7 C6 N1 116.82(12) . . ? C11 C6 N1 124.33(12) . . ? C6 C7 C8 121.43(13) . . ? C6 C7 H7 119.6(10) . . ? C8 C7 H7 118.9(10) . . ? C7 C8 C9 119.14(13) . . ? C7 C8 H8 120.5(9) . . ? C9 C8 H8 120.3(9) . . ? O2 C9 C8 125.03(12) . . ? O2 C9 C10 115.10(12) . . ? C8 C9 C10 119.86(13) . . ? C11 C10 C9 120.68(13) . . ? C11 C10 H10 120.1(10) . . ? C9 C10 H10 119.2(10) . . ? C10 C11 C6 120.04(13) . . ? C10 C11 H11 121.0(9) . . ? C6 C11 H11 119.0(9) . . ? N3 C12 H121 111.3(12) . . ? N3 C12 H122 111.4(12) . . ? H121 C12 H122 108.3(16) . . ? N3 C12 H123 106.5(11) . . ? H121 C12 H123 109.8(15) . . ? H122 C12 H123 109.5(15) . . ? O2 C13 H131 103.1(10) . . ? O2 C13 H132 111.0(10) . . ? H131 C13 H132 111.3(14) . . ? O2 C13 H133 111.0(10) . . ? H131 C13 H133 110.5(14) . . ? H132 C13 H133 109.9(14) . . ? _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 27.87 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 0.291 _refine_diff_density_min -0.266 _refine_diff_density_rms 0.038 ###END=== data_(4) _database_code_depnum_ccdc_archive 'CCDC 633160' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C18 H19 N3 O' _chemical_formula_sum 'C18 H19 N3 O' _chemical_formula_weight 293.36 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 8.1028(2) _cell_length_b 10.4312(2) _cell_length_c 10.4731(2) _cell_angle_alpha 67.932(1) _cell_angle_beta 76.578(1) _cell_angle_gamma 71.720(1) _cell_volume 772.36(3) _cell_formula_units_Z 2 _cell_measurement_temperature 150 _cell_measurement_reflns_used 10832 _cell_measurement_theta_min 2.67 _cell_measurement_theta_max 30.00 _exptl_crystal_description irregular _exptl_crystal_colour yellow _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.32 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.261 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 312 _exptl_absorpt_coefficient_mu 0.080 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 150 _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_measurement_method '\f scans and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 15532 _diffrn_reflns_av_R_equivalents 0.0290 _diffrn_reflns_av_sigmaI/netI 0.0320 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.67 _diffrn_reflns_theta_max 30.00 _reflns_number_total 4472 _reflns_number_gt 3588 _reflns_threshold_expression I>2sigma(I) _computing_data_collection 'COLLECT (Nonius, 1997)' _computing_cell_refinement 'Denzo SMN (Otwinowski & Minor, 1997)' _computing_data_reduction 'Denzo SMN (Otwinowski & Minor, 1997)' _computing_structure_solution 'SIR97 (Altomare et al., 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEPIII (Burnett & Johnson, 1996)' _computing_publication_material ; SHELXL-97 (Sheldrick, 1997), PARST (Nardelli, 1995) ; _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^)+(0.0662P)^2^+0.1076P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4472 _refine_ls_number_parameters 278 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0555 _refine_ls_R_factor_gt 0.0432 _refine_ls_wR_factor_ref 0.1242 _refine_ls_wR_factor_gt 0.1144 _refine_ls_goodness_of_fit_ref 1.052 _refine_ls_restrained_S_all 1.052 _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 O1 O 0.69519(10) 0.26911(8) 0.58162(8) 0.03588(19) Uani 1 1 d . . . N1 N 0.35137(10) 0.45789(9) 0.92005(8) 0.02396(17) Uani 1 1 d . . . H1 H 0.361(9) 0.559(8) 0.889(8) 0.029 Uiso 0.173(19) 1 d P . . N2 N 0.43470(10) 0.35601(8) 0.87104(8) 0.02433(17) Uani 1 1 d . . . N3 N 0.49160(10) 0.63170(8) 0.70907(8) 0.02442(17) Uani 1 1 d . . . H3 H 0.415(2) 0.6076(16) 0.7915(17) 0.029 Uiso 0.827(19) 1 d P . . C1 C 0.54559(11) 0.38462(10) 0.74809(9) 0.02340(18) Uani 1 1 d . . . C2 C 0.57982(11) 0.52115(10) 0.66871(9) 0.02333(19) Uani 1 1 d . . . C3 C 0.61639(12) 0.26160(10) 0.69891(10) 0.0276(2) Uani 1 1 d . . . C4 C 0.71543(13) 0.54259(11) 0.54256(10) 0.0289(2) Uani 1 1 d . . . C5 C 0.5843(2) 0.11890(13) 0.79445(14) 0.0428(3) Uani 1 1 d . . . C6 C 0.23225(11) 0.41813(10) 1.04272(9) 0.02406(19) Uani 1 1 d . . . C7 C 0.14635(13) 0.52292(11) 1.10403(10) 0.0282(2) Uani 1 1 d . . . C8 C 0.02045(14) 0.49547(12) 1.21978(10) 0.0326(2) Uani 1 1 d . . . C9 C -0.02038(13) 0.36396(12) 1.27443(10) 0.0335(2) Uani 1 1 d . . . C10 C 0.06572(14) 0.25933(12) 1.21334(11) 0.0349(2) Uani 1 1 d . . . C11 C 0.19193(13) 0.28518(11) 1.09753(10) 0.0306(2) Uani 1 1 d . . . C12 C 0.51027(13) 0.77809(10) 0.63813(11) 0.0288(2) Uani 1 1 d . . . C13 C 0.35571(13) 0.88314(10) 0.68535(10) 0.0274(2) Uani 1 1 d . . . C14 C 0.32610(14) 0.88391(12) 0.82146(11) 0.0346(2) Uani 1 1 d . . . C15 C 0.18576(16) 0.98464(14) 0.86206(13) 0.0419(3) Uani 1 1 d . . . C16 C 0.07526(16) 1.08445(13) 0.76687(14) 0.0423(3) Uani 1 1 d . . . C17 C 0.10258(16) 1.08282(12) 0.63234(13) 0.0418(3) Uani 1 1 d . . . C18 C 0.24206(14) 0.98193(12) 0.59206(11) 0.0343(2) Uani 1 1 d . . . H41 H 0.6701(19) 0.5572(15) 0.4580(15) 0.046(4) Uiso 1 1 d . . . H42 H 0.8148(18) 0.4570(15) 0.5527(14) 0.041(3) Uiso 1 1 d . . . H43 H 0.761(2) 0.6289(16) 0.5272(15) 0.050(4) Uiso 1 1 d . . . H51 H 0.463(3) 0.124(2) 0.793(2) 0.087(6) Uiso 1 1 d . . . H52 H 0.661(2) 0.044(2) 0.7575(18) 0.073(5) Uiso 1 1 d . . . H53 H 0.589(2) 0.0971(19) 0.8922(19) 0.069(5) Uiso 1 1 d . . . H7 H 0.1745(18) 0.6181(15) 1.0630(14) 0.041(3) Uiso 1 1 d . . . H8 H -0.0408(19) 0.5698(16) 1.2623(15) 0.045(4) Uiso 1 1 d . . . H9 H -0.1142(18) 0.3472(15) 1.3551(14) 0.040(3) Uiso 1 1 d . . . H10 H 0.0380(18) 0.1657(16) 1.2490(14) 0.045(4) Uiso 1 1 d . . . H11 H 0.2532(19) 0.2126(16) 1.0505(15) 0.049(4) Uiso 1 1 d . . . H121 H 0.6202(17) 0.7836(14) 0.6596(13) 0.036(3) Uiso 1 1 d . . . H122 H 0.5186(17) 0.8003(14) 0.5361(14) 0.035(3) Uiso 1 1 d . . . H14 H 0.4051(18) 0.8161(15) 0.8858(14) 0.040(3) Uiso 1 1 d . . . H15 H 0.168(2) 0.9838(17) 0.9579(16) 0.055(4) Uiso 1 1 d . . . H16 H -0.022(2) 1.1576(17) 0.7959(16) 0.052(4) Uiso 1 1 d . . . H17 H 0.021(2) 1.1493(18) 0.5688(17) 0.060(4) Uiso 1 1 d . . . H18 H 0.2584(18) 0.9801(15) 0.4964(15) 0.044(4) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0404(4) 0.0337(4) 0.0303(4) -0.0152(3) 0.0038(3) -0.0053(3) N1 0.0230(4) 0.0253(4) 0.0215(4) -0.0068(3) 0.0002(3) -0.0066(3) N2 0.0242(4) 0.0257(4) 0.0214(4) -0.0071(3) -0.0016(3) -0.0057(3) N3 0.0244(4) 0.0233(4) 0.0233(4) -0.0060(3) 0.0008(3) -0.0077(3) C1 0.0221(4) 0.0247(4) 0.0214(4) -0.0073(3) -0.0017(3) -0.0044(3) C2 0.0208(4) 0.0274(4) 0.0213(4) -0.0076(3) -0.0027(3) -0.0059(3) C3 0.0263(4) 0.0269(5) 0.0275(4) -0.0093(4) -0.0032(3) -0.0034(4) C4 0.0258(5) 0.0322(5) 0.0254(4) -0.0091(4) 0.0037(3) -0.0083(4) C5 0.0573(8) 0.0272(5) 0.0394(6) -0.0120(5) 0.0061(5) -0.0122(5) C6 0.0223(4) 0.0275(4) 0.0192(4) -0.0048(3) -0.0018(3) -0.0062(3) C7 0.0279(5) 0.0314(5) 0.0249(4) -0.0099(4) -0.0008(3) -0.0081(4) C8 0.0289(5) 0.0425(6) 0.0249(5) -0.0137(4) 0.0003(4) -0.0063(4) C9 0.0267(5) 0.0449(6) 0.0215(4) -0.0049(4) 0.0009(3) -0.0095(4) C10 0.0334(5) 0.0339(5) 0.0299(5) -0.0012(4) 0.0008(4) -0.0132(4) C11 0.0306(5) 0.0278(5) 0.0281(5) -0.0055(4) 0.0008(4) -0.0081(4) C12 0.0297(5) 0.0247(4) 0.0295(5) -0.0075(4) 0.0045(4) -0.0111(4) C13 0.0280(4) 0.0233(4) 0.0306(5) -0.0076(4) 0.0017(3) -0.0113(3) C14 0.0315(5) 0.0389(6) 0.0335(5) -0.0138(4) -0.0032(4) -0.0074(4) C15 0.0375(6) 0.0507(7) 0.0430(6) -0.0264(5) 0.0026(5) -0.0107(5) C16 0.0344(5) 0.0317(5) 0.0579(7) -0.0186(5) 0.0049(5) -0.0076(4) C17 0.0370(6) 0.0296(5) 0.0436(6) -0.0004(5) -0.0017(5) -0.0048(4) C18 0.0359(5) 0.0307(5) 0.0293(5) -0.0026(4) 0.0002(4) -0.0111(4) _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 C3 1.2319(12) . ? N1 N2 1.2835(11) . ? N1 C6 1.4245(11) . ? N1 H1 1.00(8) . ? N2 C1 1.3773(11) . ? N3 C2 1.3147(12) . ? N3 C12 1.4652(12) . ? N3 H3 0.936(17) . ? C1 C2 1.4309(13) . ? C1 C3 1.4624(13) . ? C2 C4 1.5037(13) . ? C3 C5 1.5123(15) . ? C4 H41 0.978(15) . ? C4 H42 0.987(14) . ? C4 H43 1.023(16) . ? C5 H51 0.97(2) . ? C5 H52 0.977(19) . ? C5 H53 0.970(18) . ? C6 C7 1.3908(13) . ? C6 C11 1.3994(14) . ? C7 C8 1.3930(13) . ? C7 H7 0.999(14) . ? C8 C9 1.3877(16) . ? C8 H8 0.981(14) . ? C9 C10 1.3881(16) . ? C9 H9 0.998(14) . ? C10 C11 1.3932(14) . ? C10 H10 0.984(15) . ? C11 H11 0.997(15) . ? C12 C13 1.5075(13) . ? C12 H121 0.991(13) . ? C12 H122 0.996(13) . ? C13 C18 1.3894(15) . ? C13 C14 1.3922(15) . ? C14 C15 1.3927(16) . ? C14 H14 0.961(14) . ? C15 C16 1.3890(19) . ? C15 H15 0.977(16) . ? C16 C17 1.3803(19) . ? C16 H16 0.989(16) . ? C17 C18 1.3889(16) . ? C17 H17 0.963(17) . ? C18 H18 0.986(14) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N2 N1 C6 114.32(8) . . ? N2 N1 H1 130(4) . . ? C6 N1 H1 115(4) . . ? N1 N2 C1 119.18(8) . . ? C2 N3 C12 125.18(8) . . ? C2 N3 H3 112.9(9) . . ? C12 N3 H3 121.9(9) . . ? N2 C1 C2 125.11(8) . . ? N2 C1 C3 112.54(8) . . ? C2 C1 C3 122.17(8) . . ? N3 C2 C1 118.75(8) . . ? N3 C2 C4 118.67(8) . . ? C1 C2 C4 122.56(8) . . ? O1 C3 C1 123.44(9) . . ? O1 C3 C5 118.09(9) . . ? C1 C3 C5 118.41(9) . . ? C2 C4 H41 112.5(8) . . ? C2 C4 H42 110.7(8) . . ? H41 C4 H42 105.4(11) . . ? C2 C4 H43 110.6(8) . . ? H41 C4 H43 108.3(12) . . ? H42 C4 H43 109.1(12) . . ? C3 C5 H51 106.3(12) . . ? C3 C5 H52 108.8(11) . . ? H51 C5 H52 109.4(16) . . ? C3 C5 H53 115.9(11) . . ? H51 C5 H53 102.9(15) . . ? H52 C5 H53 113.0(14) . . ? C7 C6 C11 119.87(9) . . ? C7 C6 N1 116.34(8) . . ? C11 C6 N1 123.68(9) . . ? C6 C7 C8 120.01(9) . . ? C6 C7 H7 119.2(8) . . ? C8 C7 H7 120.8(8) . . ? C9 C8 C7 120.39(10) . . ? C9 C8 H8 119.7(8) . . ? C7 C8 H8 119.9(9) . . ? C8 C9 C10 119.55(9) . . ? C8 C9 H9 119.5(8) . . ? C10 C9 H9 121.0(8) . . ? C9 C10 C11 120.73(10) . . ? C9 C10 H10 121.3(8) . . ? C11 C10 H10 118.0(8) . . ? C10 C11 C6 119.44(10) . . ? C10 C11 H11 122.1(9) . . ? C6 C11 H11 118.4(8) . . ? N3 C12 C13 110.67(7) . . ? N3 C12 H121 108.2(8) . . ? C13 C12 H121 110.3(7) . . ? N3 C12 H122 109.0(7) . . ? C13 C12 H122 109.7(7) . . ? H121 C12 H122 109.0(11) . . ? C18 C13 C14 119.24(10) . . ? C18 C13 C12 119.94(9) . . ? C14 C13 C12 120.81(9) . . ? C13 C14 C15 120.00(10) . . ? C13 C14 H14 119.3(8) . . ? C15 C14 H14 120.7(8) . . ? C16 C15 C14 120.07(11) . . ? C16 C15 H15 121.4(9) . . ? C14 C15 H15 118.6(9) . . ? C17 C16 C15 120.14(11) . . ? C17 C16 H16 120.4(9) . . ? C15 C16 H16 119.4(9) . . ? C16 C17 C18 119.77(11) . . ? C16 C17 H17 119.3(10) . . ? C18 C17 H17 120.9(10) . . ? C17 C18 C13 120.76(10) . . ? C17 C18 H18 119.0(8) . . ? C13 C18 H18 120.2(8) . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 29.99 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.241 _refine_diff_density_min -0.197 _refine_diff_density_rms 0.041 ###END=== # Attachment 'struct(5-9)2.cif' data_(5) _database_code_depnum_ccdc_archive 'CCDC 633161' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C18 H19 N3 O' _chemical_formula_sum 'C18 H19 N3 O' _chemical_formula_weight 293.36 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' _cell_length_a 7.7167(1) _cell_length_b 10.8913(1) _cell_length_c 18.8973(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1588.22(4) _cell_formula_units_Z 4 _cell_measurement_temperature 150 _cell_measurement_reflns_used 2567 _cell_measurement_theta_min 2.8 _cell_measurement_theta_max 30.0 _exptl_crystal_description irregular _exptl_crystal_colour orange _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.227 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 624 _exptl_absorpt_coefficient_mu 0.078 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 150 _diffrn_radiation_wavelength 0.71070 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_measurement_method '\f scans and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 27707 _diffrn_reflns_av_R_equivalents 0.0510 _diffrn_reflns_av_sigmaI/netI 0.0257 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 2.8 _diffrn_reflns_theta_max 30.0 _reflns_number_total 4544 _reflns_number_gt 4176 _reflns_threshold_expression I>2sigma(I) _computing_data_collection 'COLLECT (Nonius, 1997)' _computing_cell_refinement 'Denzo SMN (Otwinowski & Minor, 1997)' _computing_data_reduction 'Denzo SMN (Otwinowski & Minor, 1997)' _computing_structure_solution 'SIR97 (Altomare et al., 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEPIII (Burnett & Johnson, 1996)' _computing_publication_material ; SHELXL-97 (Sheldrick, 1997), PARST (Nardelli, 1995) ; _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^)+(0.0459P)^2^+0.2225P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 1.9(11) _refine_ls_number_reflns 4544 _refine_ls_number_parameters 278 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0421 _refine_ls_R_factor_gt 0.0368 _refine_ls_wR_factor_ref 0.0932 _refine_ls_wR_factor_gt 0.0894 _refine_ls_goodness_of_fit_ref 1.022 _refine_ls_restrained_S_all 1.022 _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 O1 O -0.11066(12) 1.07887(10) 1.02433(5) 0.0452(2) Uani 1 1 d . . . N1 N 0.19465(12) 1.00658(9) 0.82056(5) 0.0335(2) Uani 1 1 d . . . H1 H 0.208(11) 1.083(8) 0.799(4) 0.040 Uiso 0.18(3) 1 d P . . N2 N 0.13743(12) 0.98121(9) 0.88293(5) 0.03218(19) Uani 1 1 d . . . N3 N 0.14192(15) 1.23640(9) 0.84517(6) 0.0382(2) Uani 1 1 d . . . H3 H 0.180(3) 1.172(2) 0.8170(11) 0.046 Uiso 0.82(3) 1 d P . . C1 C 0.07851(14) 1.07577(11) 0.92491(6) 0.0333(2) Uani 1 1 d . . . C2 C 0.07523(14) 1.20207(11) 0.90650(6) 0.0353(2) Uani 1 1 d . . . C3 C 0.01425(15) 1.03180(11) 0.99419(6) 0.0345(2) Uani 1 1 d . . . C4 C 0.00317(18) 1.29970(12) 0.95354(8) 0.0431(3) Uani 1 1 d . . . C5 C 0.10712(15) 0.92786(10) 1.02983(6) 0.0325(2) Uani 1 1 d . . . C6 C 0.28342(15) 0.90551(11) 1.01944(6) 0.0350(2) Uani 1 1 d . . . C7 C 0.36621(17) 0.81289(13) 1.05691(7) 0.0407(3) Uani 1 1 d . . . C8 C 0.27365(19) 0.74096(13) 1.10452(7) 0.0451(3) Uani 1 1 d . . . C9 C 0.09897(19) 0.76319(13) 1.11565(8) 0.0450(3) Uani 1 1 d . . . C10 C 0.01672(17) 0.85711(12) 1.07922(7) 0.0388(3) Uani 1 1 d . . . C11 C 0.24117(14) 0.90137(10) 0.78028(6) 0.0315(2) Uani 1 1 d . . . C12 C 0.33469(16) 0.92216(11) 0.71853(6) 0.0368(2) Uani 1 1 d . . . C13 C 0.38109(17) 0.82479(12) 0.67509(6) 0.0390(3) Uani 1 1 d . . . C14 C 0.33352(16) 0.70444(11) 0.69140(6) 0.0360(2) Uani 1 1 d . . . C15 C 0.23952(18) 0.68528(11) 0.75345(6) 0.0395(3) Uani 1 1 d . . . C16 C 0.19381(17) 0.78149(11) 0.79777(6) 0.0361(2) Uani 1 1 d . . . C17 C 0.1530(2) 1.36327(12) 0.82019(8) 0.0452(3) Uani 1 1 d . . . C18 C 0.3789(2) 0.59908(14) 0.64315(8) 0.0460(3) Uani 1 1 d . . . H41 H -0.028(3) 1.264(2) 1.0038(12) 0.081(6) Uiso 1 1 d . . . H42 H 0.078(3) 1.369(2) 0.9550(12) 0.084(7) Uiso 1 1 d . . . H43 H -0.107(3) 1.335(2) 0.9367(13) 0.094(7) Uiso 1 1 d . . . H6 H 0.355(2) 0.9562(14) 0.9871(8) 0.041(4) Uiso 1 1 d . . . H7 H 0.492(2) 0.7977(15) 1.0470(9) 0.051(4) Uiso 1 1 d . . . H8 H 0.331(2) 0.6698(16) 1.1291(9) 0.051(4) Uiso 1 1 d . . . H9 H 0.033(2) 0.7137(16) 1.1500(9) 0.056(5) Uiso 1 1 d . . . H10 H -0.106(2) 0.8726(14) 1.0834(8) 0.041(4) Uiso 1 1 d . . . H12 H 0.366(2) 1.0082(15) 0.7054(9) 0.048(4) Uiso 1 1 d . . . H13 H 0.449(2) 0.8393(15) 0.6296(9) 0.047(4) Uiso 1 1 d . . . H15 H 0.204(2) 0.5989(16) 0.7664(8) 0.049(4) Uiso 1 1 d . . . H16 H 0.132(2) 0.7670(16) 0.8413(9) 0.050(4) Uiso 1 1 d . . . H171 H 0.036(2) 1.4041(17) 0.8179(9) 0.056(5) Uiso 1 1 d . . . H173 H 0.201(2) 1.3640(16) 0.7731(10) 0.054(5) Uiso 1 1 d . . . H172 H 0.229(2) 1.4153(16) 0.8518(9) 0.055(4) Uiso 1 1 d . . . H181 H 0.504(3) 0.613(2) 0.6219(12) 0.081(6) Uiso 1 1 d . . . H182 H 0.298(3) 0.595(2) 0.6026(11) 0.071(6) Uiso 1 1 d . . . H183 H 0.384(3) 0.520(2) 0.6659(13) 0.097(8) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0388(4) 0.0536(5) 0.0433(5) -0.0008(4) 0.0060(4) 0.0122(4) N1 0.0340(4) 0.0344(5) 0.0322(4) 0.0017(4) 0.0004(4) -0.0002(4) N2 0.0295(4) 0.0356(4) 0.0315(4) -0.0008(4) -0.0017(4) -0.0004(4) N3 0.0415(5) 0.0331(5) 0.0401(5) 0.0021(4) -0.0063(4) 0.0013(4) C1 0.0304(5) 0.0345(5) 0.0349(5) -0.0020(4) -0.0018(4) 0.0021(4) C2 0.0309(5) 0.0364(5) 0.0387(6) -0.0023(4) -0.0078(4) 0.0022(4) C3 0.0314(5) 0.0376(5) 0.0345(5) -0.0039(4) -0.0002(4) 0.0016(4) C4 0.0408(6) 0.0372(6) 0.0512(7) -0.0078(5) -0.0027(6) 0.0035(5) C5 0.0324(5) 0.0334(5) 0.0317(5) -0.0048(4) -0.0003(4) -0.0012(4) C6 0.0327(5) 0.0384(5) 0.0339(5) -0.0011(4) 0.0005(4) -0.0010(4) C7 0.0359(6) 0.0451(6) 0.0411(6) -0.0013(5) -0.0003(5) 0.0050(5) C8 0.0486(7) 0.0400(6) 0.0468(7) 0.0053(5) -0.0012(6) 0.0047(5) C9 0.0452(7) 0.0416(6) 0.0483(7) 0.0065(6) 0.0048(6) -0.0032(5) C10 0.0346(6) 0.0415(6) 0.0401(6) -0.0008(5) 0.0032(5) -0.0023(5) C11 0.0305(5) 0.0335(5) 0.0306(5) 0.0021(4) -0.0029(4) 0.0000(4) C12 0.0413(6) 0.0366(6) 0.0326(5) 0.0020(4) 0.0023(4) -0.0040(5) C13 0.0408(6) 0.0450(6) 0.0313(5) -0.0001(5) 0.0031(5) -0.0021(5) C14 0.0360(6) 0.0386(6) 0.0334(5) -0.0027(4) -0.0057(4) 0.0044(5) C15 0.0445(6) 0.0332(5) 0.0408(6) 0.0035(5) -0.0010(5) 0.0011(5) C16 0.0394(6) 0.0348(5) 0.0341(5) 0.0049(4) 0.0028(5) 0.0001(4) C17 0.0517(7) 0.0341(6) 0.0497(7) 0.0062(5) -0.0126(6) -0.0008(5) C18 0.0494(7) 0.0447(7) 0.0439(7) -0.0099(5) -0.0061(6) 0.0089(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C3 1.2314(14) . ? N1 N2 1.2885(14) . ? N1 C11 1.4218(15) . ? N1 H1 0.94(9) . ? N2 C1 1.3772(14) . ? N3 C2 1.3221(16) . ? N3 C17 1.4627(16) . ? N3 H3 0.93(2) . ? C1 C2 1.4191(16) . ? C1 C3 1.4797(16) . ? C2 C4 1.4934(17) . ? C3 C5 1.4996(16) . ? C4 H41 1.05(2) . ? C4 H42 0.95(2) . ? C4 H43 0.99(3) . ? C5 C6 1.3959(16) . ? C5 C10 1.3969(17) . ? C6 C7 1.3882(17) . ? C6 H6 0.990(16) . ? C7 C8 1.3905(19) . ? C7 H7 0.999(19) . ? C8 C9 1.386(2) . ? C8 H8 1.007(18) . ? C9 C10 1.3868(19) . ? C9 H9 0.986(18) . ? C10 H10 0.965(16) . ? C11 C12 1.3905(16) . ? C11 C16 1.3955(15) . ? C12 C13 1.3881(18) . ? C12 H12 0.998(16) . ? C13 C14 1.3957(18) . ? C13 H13 1.018(17) . ? C14 C15 1.3944(17) . ? C14 C18 1.5069(17) . ? C15 C16 1.3871(17) . ? C15 H15 1.011(17) . ? C16 H16 0.964(18) . ? C17 H171 1.010(19) . ? C17 H173 0.963(19) . ? C17 H172 1.009(18) . ? C18 H181 1.05(2) . ? C18 H182 0.99(2) . ? C18 H183 0.97(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N2 N1 C11 113.79(9) . . ? N2 N1 H1 129(5) . . ? C11 N1 H1 117(5) . . ? N1 N2 C1 118.66(10) . . ? C2 N3 C17 124.95(12) . . ? C2 N3 H3 114.2(12) . . ? C17 N3 H3 120.8(12) . . ? N2 C1 C2 126.13(11) . . ? N2 C1 C3 112.23(10) . . ? C2 C1 C3 121.64(10) . . ? N3 C2 C1 118.82(11) . . ? N3 C2 C4 117.74(11) . . ? C1 C2 C4 123.43(12) . . ? O1 C3 C1 122.47(11) . . ? O1 C3 C5 118.73(11) . . ? C1 C3 C5 118.79(10) . . ? C2 C4 H41 111.1(13) . . ? C2 C4 H42 110.7(14) . . ? H41 C4 H42 113.7(19) . . ? C2 C4 H43 114.2(14) . . ? H41 C4 H43 103.9(19) . . ? H42 C4 H43 102.9(19) . . ? C6 C5 C10 118.98(11) . . ? C6 C5 C3 122.29(10) . . ? C10 C5 C3 118.54(10) . . ? C7 C6 C5 120.23(11) . . ? C7 C6 H6 117.6(9) . . ? C5 C6 H6 122.1(9) . . ? C6 C7 C8 120.20(12) . . ? C6 C7 H7 118.1(10) . . ? C8 C7 H7 121.7(9) . . ? C9 C8 C7 119.97(13) . . ? C9 C8 H8 119.6(10) . . ? C7 C8 H8 120.3(10) . . ? C8 C9 C10 119.92(13) . . ? C8 C9 H9 120.5(11) . . ? C10 C9 H9 119.6(11) . . ? C9 C10 C5 120.66(12) . . ? C9 C10 H10 122.5(9) . . ? C5 C10 H10 116.6(9) . . ? C12 C11 C16 119.15(11) . . ? C12 C11 N1 116.68(10) . . ? C16 C11 N1 124.13(10) . . ? C13 C12 C11 120.38(11) . . ? C13 C12 H12 120.5(10) . . ? C11 C12 H12 119.1(10) . . ? C12 C13 C14 121.27(11) . . ? C12 C13 H13 120.9(9) . . ? C14 C13 H13 117.8(9) . . ? C15 C14 C13 117.58(11) . . ? C15 C14 C18 121.05(12) . . ? C13 C14 C18 121.35(12) . . ? C16 C15 C14 121.80(11) . . ? C16 C15 H15 119.2(10) . . ? C14 C15 H15 119.0(9) . . ? C15 C16 C11 119.81(11) . . ? C15 C16 H16 121.2(10) . . ? C11 C16 H16 119.0(10) . . ? N3 C17 H171 112.1(11) . . ? N3 C17 H173 109.2(10) . . ? H171 C17 H173 107.4(14) . . ? N3 C17 H172 111.9(10) . . ? H171 C17 H172 107.3(14) . . ? H173 C17 H172 108.7(15) . . ? C14 C18 H181 109.7(12) . . ? C14 C18 H182 110.8(12) . . ? H181 C18 H182 106.6(16) . . ? C14 C18 H183 114.9(15) . . ? H181 C18 H183 105.1(19) . . ? H182 C18 H183 109(2) . . ? _diffrn_measured_fraction_theta_max 0.983 _diffrn_reflns_theta_full 30.03 _diffrn_measured_fraction_theta_full 0.983 _refine_diff_density_max 0.172 _refine_diff_density_min -0.124 _refine_diff_density_rms 0.028 ###END=== data_(6) _database_code_depnum_ccdc_archive 'CCDC 633162' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C17 H16 N4 O3' _chemical_formula_sum 'C17 H16 N4 O3' _chemical_formula_weight 324.34 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 'P 21/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 8.0995(1) _cell_length_b 9.5542(2) _cell_length_c 20.4491(4) _cell_angle_alpha 90.00 _cell_angle_beta 98.2804(8) _cell_angle_gamma 90.00 _cell_volume 1565.94(5) _cell_formula_units_Z 4 _cell_measurement_temperature 150 _cell_measurement_reflns_used 4286 _cell_measurement_theta_min 2.5 _cell_measurement_theta_max 30.0 _exptl_crystal_description prismatic _exptl_crystal_colour orange _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.376 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 680 _exptl_absorpt_coefficient_mu 0.097 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 150 _diffrn_radiation_wavelength 0.71070 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_measurement_method '\f scans and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 24759 _diffrn_reflns_av_R_equivalents 0.0580 _diffrn_reflns_av_sigmaI/netI 0.0389 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_theta_min 2.5 _diffrn_reflns_theta_max 30.0 _reflns_number_total 4463 _reflns_number_gt 3343 _reflns_threshold_expression I>2sigma(I) _computing_data_collection 'COLLECT (Nonius, 1997)' _computing_cell_refinement 'Denzo SMN (Otwinowski & Minor, 1997)' _computing_data_reduction 'Denzo SMN (Otwinowski & Minor, 1997)' _computing_structure_solution 'SIR97 (Altomare et al., 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEPIII (Burnett & Johnson, 1996)' _computing_publication_material ; SHELXL-97 (Sheldrick, 1997), PARST (Nardelli, 1995) ; _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^)+(0.0570P)^2^+0.4945P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4463 _refine_ls_number_parameters 284 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0747 _refine_ls_R_factor_gt 0.0493 _refine_ls_wR_factor_ref 0.1316 _refine_ls_wR_factor_gt 0.1141 _refine_ls_goodness_of_fit_ref 1.037 _refine_ls_restrained_S_all 1.037 _refine_ls_shift/su_max 0.000 _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 0.36632(15) 0.71377(11) 0.19497(5) 0.0432(3) Uani 1 1 d . . . O2 O -0.19224(15) 0.54000(13) -0.26514(6) 0.0521(3) Uani 1 1 d . . . O3 O -0.07688(14) 0.34179(15) -0.28298(5) 0.0547(3) Uani 1 1 d . . . N1 N 0.28400(14) 0.44918(12) 0.00557(5) 0.0291(2) Uani 1 1 d . . . H1 H 0.316(12) 0.363(11) 0.025(5) 0.035 Uiso 0.17(2) 1 d P . . N2 N 0.28589(13) 0.56569(11) 0.03821(5) 0.0281(2) Uani 1 1 d . . . N3 N 0.46014(15) 0.33578(13) 0.10664(6) 0.0327(3) Uani 1 1 d . . . H3 H 0.400(3) 0.331(2) 0.0662(11) 0.039 Uiso 0.83(2) 1 d P . . N4 N -0.09684(15) 0.44279(15) -0.24754(6) 0.0404(3) Uani 1 1 d . . . C1 C 0.37051(16) 0.57240(14) 0.10053(6) 0.0292(3) Uani 1 1 d . . . C2 C 0.46319(16) 0.45892(14) 0.13515(6) 0.0297(3) Uani 1 1 d . . . C3 C 0.34579(17) 0.70498(15) 0.13434(6) 0.0317(3) Uani 1 1 d . . . C4 C 0.56644(19) 0.47505(17) 0.20161(7) 0.0361(3) Uani 1 1 d . . . C5 C 0.28597(16) 0.83364(14) 0.09544(6) 0.0296(3) Uani 1 1 d . . . C6 C 0.32844(17) 0.86707(15) 0.03348(7) 0.0317(3) Uani 1 1 d . . . C7 C 0.27224(18) 0.99098(15) 0.00224(7) 0.0346(3) Uani 1 1 d . . . C8 C 0.17148(18) 1.08140(16) 0.03187(7) 0.0365(3) Uani 1 1 d . . . C9 C 0.12954(19) 1.04968(16) 0.09383(7) 0.0374(3) Uani 1 1 d . . . C10 C 0.18819(18) 0.92759(15) 0.12546(7) 0.0345(3) Uani 1 1 d . . . C11 C 0.18656(15) 0.45626(14) -0.05750(6) 0.0279(3) Uani 1 1 d . . . C12 C 0.19516(17) 0.33997(15) -0.09826(6) 0.0309(3) Uani 1 1 d . . . C13 C 0.10174(17) 0.33472(15) -0.16076(7) 0.0330(3) Uani 1 1 d . . . C14 C -0.00017(16) 0.44729(15) -0.18121(6) 0.0328(3) Uani 1 1 d . . . C15 C -0.01181(17) 0.56386(16) -0.14195(7) 0.0338(3) Uani 1 1 d . . . C16 C 0.08220(17) 0.56885(15) -0.07983(7) 0.0318(3) Uani 1 1 d . . . C17 C 0.5464(2) 0.21061(17) 0.13494(8) 0.0382(3) Uani 1 1 d . . . H41 H 0.599(2) 0.5732(19) 0.2099(8) 0.039(4) Uiso 1 1 d . . . H42 H 0.501(2) 0.4441(19) 0.2372(9) 0.051(5) Uiso 1 1 d . . . H43 H 0.667(2) 0.416(2) 0.2044(9) 0.049(5) Uiso 1 1 d . . . H6 H 0.397(2) 0.8037(18) 0.0124(8) 0.040(4) Uiso 1 1 d . . . H7 H 0.303(2) 1.0128(18) -0.0411(9) 0.046(5) Uiso 1 1 d . . . H8 H 0.129(2) 1.1662(18) 0.0091(8) 0.040(4) Uiso 1 1 d . . . H9 H 0.060(2) 1.113(2) 0.1152(8) 0.047(5) Uiso 1 1 d . . . H10 H 0.160(2) 0.9040(17) 0.1686(8) 0.037(4) Uiso 1 1 d . . . H12 H 0.109(2) 0.2525(19) -0.1891(8) 0.043(4) Uiso 1 1 d . . . H13 H 0.268(2) 0.2633(18) -0.0838(8) 0.037(4) Uiso 1 1 d . . . H15 H -0.086(2) 0.6393(19) -0.1575(8) 0.040(4) Uiso 1 1 d . . . H16 H 0.0780(19) 0.6492(18) -0.0511(8) 0.037(4) Uiso 1 1 d . . . H171 H 0.500(2) 0.1285(19) 0.1103(8) 0.042(4) Uiso 1 1 d . . . H172 H 0.530(2) 0.197(2) 0.1808(10) 0.062(6) Uiso 1 1 d . . . H173 H 0.665(3) 0.216(2) 0.1320(9) 0.055(5) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0677(7) 0.0361(6) 0.0248(5) -0.0016(4) 0.0033(4) 0.0015(5) O2 0.0515(7) 0.0536(7) 0.0451(6) 0.0129(5) -0.0135(5) -0.0091(6) O3 0.0473(6) 0.0824(10) 0.0327(5) -0.0182(6) -0.0001(5) -0.0031(6) N1 0.0334(6) 0.0277(6) 0.0257(5) 0.0001(4) 0.0021(4) -0.0008(4) N2 0.0315(5) 0.0273(6) 0.0255(5) -0.0007(4) 0.0042(4) -0.0030(4) N3 0.0360(6) 0.0314(6) 0.0290(5) 0.0018(5) -0.0007(4) 0.0028(5) N4 0.0356(6) 0.0537(9) 0.0305(6) 0.0030(6) 0.0000(5) -0.0120(6) C1 0.0337(6) 0.0283(6) 0.0254(6) 0.0003(5) 0.0033(5) -0.0034(5) C2 0.0294(6) 0.0331(7) 0.0267(6) 0.0018(5) 0.0047(5) -0.0030(5) C3 0.0374(7) 0.0305(7) 0.0271(6) -0.0004(5) 0.0043(5) -0.0045(5) C4 0.0382(7) 0.0384(8) 0.0299(7) 0.0025(6) -0.0008(5) -0.0022(6) C5 0.0339(6) 0.0266(6) 0.0279(6) -0.0017(5) 0.0026(5) -0.0043(5) C6 0.0344(7) 0.0298(7) 0.0314(6) -0.0013(5) 0.0064(5) -0.0025(5) C7 0.0389(7) 0.0322(7) 0.0330(7) 0.0033(6) 0.0067(5) -0.0023(6) C8 0.0393(7) 0.0305(7) 0.0390(7) 0.0024(6) 0.0030(6) 0.0007(6) C9 0.0397(7) 0.0329(8) 0.0404(8) -0.0054(6) 0.0079(6) 0.0004(6) C10 0.0400(7) 0.0338(7) 0.0304(6) -0.0041(5) 0.0074(5) -0.0056(6) C11 0.0304(6) 0.0276(6) 0.0255(6) 0.0008(5) 0.0036(5) -0.0031(5) C12 0.0355(7) 0.0276(7) 0.0294(6) 0.0001(5) 0.0040(5) -0.0015(5) C13 0.0378(7) 0.0321(7) 0.0298(6) -0.0044(5) 0.0067(5) -0.0073(6) C14 0.0313(6) 0.0404(8) 0.0258(6) 0.0005(5) 0.0007(5) -0.0088(6) C15 0.0323(6) 0.0337(7) 0.0343(7) 0.0042(6) 0.0005(5) -0.0006(6) C16 0.0338(7) 0.0294(7) 0.0317(6) -0.0022(5) 0.0024(5) -0.0008(5) C17 0.0437(8) 0.0345(8) 0.0342(7) 0.0011(6) -0.0016(6) 0.0063(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C3 1.2298(16) . ? O2 N4 1.2285(18) . ? O3 N4 1.2314(18) . ? N1 N2 1.2969(15) . ? N1 C11 1.4134(16) . ? N1 H1 0.93(11) . ? N2 C1 1.3587(16) . ? N3 C2 1.3117(18) . ? N3 C17 1.4619(18) . ? N3 H3 0.90(2) . ? N4 C14 1.4659(17) . ? C1 C2 1.4448(19) . ? C1 C3 1.4705(19) . ? C2 C4 1.4975(19) . ? C3 C5 1.5059(19) . ? C4 H41 0.983(18) . ? C4 H42 1.003(19) . ? C4 H43 0.982(19) . ? C5 C10 1.3964(19) . ? C5 C6 1.3968(18) . ? C6 C7 1.390(2) . ? C6 H6 0.967(17) . ? C7 C8 1.386(2) . ? C7 H7 0.976(17) . ? C8 C9 1.392(2) . ? C8 H8 0.973(17) . ? C9 C10 1.384(2) . ? C9 H9 0.977(18) . ? C10 H10 0.969(16) . ? C11 C12 1.3966(18) . ? C11 C16 1.4032(19) . ? C12 C13 1.3893(18) . ? C12 H13 0.962(17) . ? C13 C14 1.383(2) . ? C13 H12 0.983(18) . ? C14 C15 1.384(2) . ? C15 C16 1.3846(19) . ? C15 H15 0.961(18) . ? C16 H16 0.970(17) . ? C17 H171 0.978(18) . ? C17 H172 0.97(2) . ? C17 H173 0.97(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N2 N1 C11 113.10(11) . . ? N2 N1 H1 124(6) . . ? C11 N1 H1 121(6) . . ? N1 N2 C1 119.36(11) . . ? C2 N3 C17 125.48(12) . . ? C2 N3 H3 115.5(13) . . ? C17 N3 H3 119.0(13) . . ? O2 N4 O3 123.39(13) . . ? O2 N4 C14 118.59(13) . . ? O3 N4 C14 118.02(13) . . ? N2 C1 C2 125.49(12) . . ? N2 C1 C3 113.40(11) . . ? C2 C1 C3 120.82(11) . . ? N3 C2 C1 118.69(12) . . ? N3 C2 C4 117.91(12) . . ? C1 C2 C4 123.39(12) . . ? O1 C3 C1 121.67(12) . . ? O1 C3 C5 117.60(12) . . ? C1 C3 C5 120.66(11) . . ? C2 C4 H41 110.9(10) . . ? C2 C4 H42 110.1(10) . . ? H41 C4 H42 108.3(14) . . ? C2 C4 H43 110.0(10) . . ? H41 C4 H43 109.5(15) . . ? H42 C4 H43 108.0(15) . . ? C10 C5 C6 118.76(13) . . ? C10 C5 C3 116.88(12) . . ? C6 C5 C3 124.28(12) . . ? C7 C6 C5 120.29(13) . . ? C7 C6 H6 120.0(10) . . ? C5 C6 H6 119.7(10) . . ? C8 C7 C6 120.28(13) . . ? C8 C7 H7 120.3(10) . . ? C6 C7 H7 119.4(10) . . ? C7 C8 C9 119.90(14) . . ? C7 C8 H8 120.0(10) . . ? C9 C8 H8 120.1(10) . . ? C10 C9 C8 119.77(14) . . ? C10 C9 H9 119.9(10) . . ? C8 C9 H9 120.4(10) . . ? C9 C10 C5 120.96(13) . . ? C9 C10 H10 120.9(10) . . ? C5 C10 H10 118.2(10) . . ? C12 C11 C16 119.69(12) . . ? C12 C11 N1 115.92(12) . . ? C16 C11 N1 124.37(12) . . ? C13 C12 C11 120.68(13) . . ? C13 C12 H13 119.1(9) . . ? C11 C12 H13 120.2(9) . . ? C14 C13 C12 118.19(13) . . ? C14 C13 H12 121.8(10) . . ? C12 C13 H12 120.0(10) . . ? C13 C14 C15 122.53(12) . . ? C13 C14 N4 118.22(13) . . ? C15 C14 N4 119.24(13) . . ? C14 C15 C16 119.05(13) . . ? C14 C15 H15 120.2(10) . . ? C16 C15 H15 120.8(10) . . ? C15 C16 C11 119.86(13) . . ? C15 C16 H16 121.4(9) . . ? C11 C16 H16 118.7(9) . . ? N3 C17 H171 109.0(10) . . ? N3 C17 H172 111.4(12) . . ? H171 C17 H172 107.0(16) . . ? N3 C17 H173 110.6(11) . . ? H171 C17 H173 108.8(15) . . ? H172 C17 H173 109.9(16) . . ? _diffrn_measured_fraction_theta_max 0.970 _diffrn_reflns_theta_full 30.02 _diffrn_measured_fraction_theta_full 0.970 _refine_diff_density_max 0.241 _refine_diff_density_min -0.222 _refine_diff_density_rms 0.043 ###END=== data_(7) _database_code_depnum_ccdc_archive 'CCDC 633163' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C18 H19 N3 O2' _chemical_formula_sum 'C18 H19 N3 O2' _chemical_formula_weight 309.36 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P b c a' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y, -z-1/2' '-x-1/2, y-1/2, z' 'x, -y-1/2, z-1/2' _cell_length_a 13.6403(2) _cell_length_b 9.6489(2) _cell_length_c 24.3685(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3207.23(10) _cell_formula_units_Z 8 _cell_measurement_temperature 150 _cell_measurement_reflns_used 4934 _cell_measurement_theta_min 2.7 _cell_measurement_theta_max 28.0 _exptl_crystal_description prismatic _exptl_crystal_colour yellow _exptl_crystal_size_max 0.52 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.17 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.281 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1312 _exptl_absorpt_coefficient_mu 0.085 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 150 _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_measurement_method '\f scans and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 19780 _diffrn_reflns_av_R_equivalents 0.0330 _diffrn_reflns_av_sigmaI/netI 0.0332 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -32 _diffrn_reflns_limit_l_max 32 _diffrn_reflns_theta_min 2.7 _diffrn_reflns_theta_max 28.0 _reflns_number_total 3847 _reflns_number_gt 3084 _reflns_threshold_expression I>2sigma(I) _computing_data_collection 'COLLECT (Nonius, 1997)' _computing_cell_refinement 'Denzo SMN (Otwinowski & Minor, 1997)' _computing_data_reduction 'Denzo SMN (Otwinowski & Minor, 1997)' _computing_structure_solution 'SIR97 (Altomare et al., 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEPIII (Burnett & Johnson, 1996)' _computing_publication_material ; SHELXL-97 (Sheldrick, 1997), PARST (Nardelli, 1995) ; _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^)+(0.0472P)^2^+0.7372P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3847 _refine_ls_number_parameters 287 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0533 _refine_ls_R_factor_gt 0.0391 _refine_ls_wR_factor_ref 0.1026 _refine_ls_wR_factor_gt 0.0952 _refine_ls_goodness_of_fit_ref 1.038 _refine_ls_restrained_S_all 1.038 _refine_ls_shift/su_max 0.000 _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 0.86912(7) 0.13314(10) 0.22630(4) 0.0429(3) Uani 1 1 d . . . O2 O 0.81739(7) 0.58502(9) -0.12186(3) 0.0345(2) Uani 1 1 d . . . N1 N 0.84502(7) 0.49439(10) 0.10353(4) 0.0263(2) Uani 1 1 d . . . H1 H 0.837(7) 0.562(10) 0.126(4) 0.032 Uiso 0.15(2) 1 d P . . N2 N 0.86669(7) 0.37044(10) 0.11840(4) 0.0256(2) Uani 1 1 d . . . N3 N 0.85826(8) 0.57040(11) 0.20568(5) 0.0315(2) Uani 1 1 d . . . H3 H 0.8468(14) 0.5906(17) 0.1694(9) 0.041 Uiso 0.85(2) 1 d P . . C1 C 0.87619(8) 0.34043(12) 0.17349(5) 0.0268(2) Uani 1 1 d . . . C2 C 0.87459(8) 0.43844(13) 0.21708(5) 0.0289(3) Uani 1 1 d . . . C3 C 0.89029(9) 0.19123(12) 0.18289(5) 0.0289(3) Uani 1 1 d . . . C4 C 0.89583(13) 0.40075(17) 0.27556(6) 0.0400(3) Uani 1 1 d . . . C5 C 0.93365(9) 0.10404(11) 0.13805(5) 0.0275(3) Uani 1 1 d . . . C6 C 1.01513(10) 0.14640(12) 0.10821(5) 0.0314(3) Uani 1 1 d . . . C7 C 1.06077(12) 0.05634(14) 0.07199(6) 0.0412(3) Uani 1 1 d . . . C8 C 1.02351(13) -0.07577(14) 0.06440(6) 0.0465(4) Uani 1 1 d . . . C9 C 0.94222(12) -0.11842(14) 0.09338(7) 0.0464(4) Uani 1 1 d . . . C10 C 0.89760(10) -0.02996(13) 0.13045(6) 0.0364(3) Uani 1 1 d . . . C11 C 0.83996(8) 0.50979(11) 0.04548(5) 0.0237(2) Uani 1 1 d . . . C12 C 0.78578(9) 0.62109(11) 0.02489(5) 0.0280(3) Uani 1 1 d . . . C13 C 0.77966(10) 0.64266(12) -0.03103(5) 0.0303(3) Uani 1 1 d . . . C14 C 0.82811(9) 0.55457(11) -0.06732(5) 0.0256(2) Uani 1 1 d . . . C15 C 0.88366(9) 0.44497(11) -0.04713(5) 0.0266(2) Uani 1 1 d . . . C16 C 0.88893(9) 0.42307(11) 0.00906(5) 0.0257(2) Uani 1 1 d . . . C17 C 0.85872(12) 0.68382(15) 0.24530(6) 0.0385(3) Uani 1 1 d . . . C18 C 0.86194(12) 0.49261(15) -0.16007(6) 0.0406(3) Uani 1 1 d . . . H41 H 0.9180(14) 0.303(2) 0.2786(7) 0.064(5) Uiso 1 1 d . . . H42 H 0.9449(17) 0.457(2) 0.2897(8) 0.082(7) Uiso 1 1 d . . . H43 H 0.8391(17) 0.416(2) 0.2992(9) 0.086(7) Uiso 1 1 d . . . H6 H 1.0424(11) 0.2391(15) 0.1141(6) 0.039(4) Uiso 1 1 d . . . H7 H 1.1183(13) 0.0873(17) 0.0500(7) 0.052(5) Uiso 1 1 d . . . H8 H 1.0552(13) -0.1340(16) 0.0370(7) 0.051(4) Uiso 1 1 d . . . H9 H 0.9154(13) -0.2115(18) 0.0891(7) 0.058(5) Uiso 1 1 d . . . H10 H 0.8414(12) -0.0559(15) 0.1531(7) 0.047(4) Uiso 1 1 d . . . H12 H 0.7535(10) 0.6829(14) 0.0509(6) 0.035(4) Uiso 1 1 d . . . H13 H 0.7411(10) 0.7179(14) -0.0458(6) 0.035(4) Uiso 1 1 d . . . H15 H 0.9188(11) 0.3851(14) -0.0726(6) 0.037(4) Uiso 1 1 d . . . H16 H 0.9277(10) 0.3468(14) 0.0230(5) 0.032(4) Uiso 1 1 d . . . H171 H 0.9213(14) 0.6906(18) 0.2634(7) 0.062(5) Uiso 1 1 d . . . H172 H 0.8107(16) 0.6724(19) 0.2730(8) 0.071(6) Uiso 1 1 d . . . H173 H 0.8476(15) 0.766(2) 0.2245(8) 0.081(6) Uiso 1 1 d . . . H181 H 0.8353(12) 0.3976(16) -0.1554(6) 0.042(4) Uiso 1 1 d . . . H182 H 0.8458(12) 0.5280(16) -0.1963(7) 0.049(4) Uiso 1 1 d . . . H183 H 0.9360(13) 0.4884(16) -0.1553(6) 0.050(4) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0495(6) 0.0443(5) 0.0349(5) 0.0136(4) 0.0083(4) 0.0014(4) O2 0.0459(6) 0.0346(5) 0.0229(4) -0.0007(3) -0.0005(4) 0.0020(4) N1 0.0282(5) 0.0258(5) 0.0249(5) -0.0005(4) -0.0008(4) 0.0010(4) N2 0.0235(5) 0.0268(5) 0.0266(5) 0.0018(4) -0.0001(4) 0.0000(4) N3 0.0321(5) 0.0357(5) 0.0265(5) -0.0050(4) -0.0011(4) 0.0032(4) C1 0.0240(6) 0.0325(6) 0.0239(6) 0.0013(4) -0.0005(4) 0.0004(4) C2 0.0218(6) 0.0385(6) 0.0264(6) -0.0005(5) 0.0001(4) -0.0007(5) C3 0.0246(6) 0.0339(6) 0.0283(6) 0.0061(5) -0.0016(5) -0.0011(5) C4 0.0471(8) 0.0473(8) 0.0256(7) -0.0014(6) -0.0066(6) -0.0001(7) C5 0.0280(6) 0.0267(5) 0.0279(6) 0.0056(4) -0.0074(5) 0.0010(4) C6 0.0352(7) 0.0259(6) 0.0332(6) 0.0019(5) 0.0002(5) 0.0004(5) C7 0.0489(8) 0.0345(7) 0.0403(8) 0.0018(6) 0.0085(6) 0.0084(6) C8 0.0640(10) 0.0329(7) 0.0427(8) -0.0062(6) -0.0054(7) 0.0132(7) C9 0.0551(9) 0.0256(6) 0.0584(9) -0.0044(6) -0.0212(8) 0.0000(6) C10 0.0332(7) 0.0294(6) 0.0467(8) 0.0080(5) -0.0115(6) -0.0034(5) C11 0.0246(5) 0.0224(5) 0.0242(5) -0.0011(4) -0.0011(4) -0.0028(4) C12 0.0317(6) 0.0244(5) 0.0279(6) -0.0031(4) 0.0009(5) 0.0035(5) C13 0.0348(7) 0.0255(5) 0.0306(6) 0.0015(5) -0.0018(5) 0.0059(5) C14 0.0285(6) 0.0260(5) 0.0223(5) -0.0004(4) -0.0014(5) -0.0048(4) C15 0.0280(6) 0.0231(5) 0.0288(6) -0.0047(4) 0.0027(5) -0.0011(4) C16 0.0275(6) 0.0216(5) 0.0280(6) -0.0001(4) -0.0015(5) 0.0011(4) C17 0.0419(8) 0.0417(7) 0.0320(7) -0.0109(6) -0.0028(6) 0.0000(6) C18 0.0541(9) 0.0426(7) 0.0249(7) -0.0054(6) 0.0032(6) 0.0001(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C3 1.2316(14) . ? O2 C14 1.3690(14) . ? O2 C18 1.4253(16) . ? N1 N2 1.2842(13) . ? N1 C11 1.4239(15) . ? N1 H1 0.86(11) . ? N2 C1 1.3795(14) . ? N3 C2 1.3222(16) . ? N3 C17 1.4594(17) . ? N3 H3 0.92(2) . ? C1 C2 1.4223(16) . ? C1 C3 1.4703(16) . ? C2 C4 1.4989(17) . ? C3 C5 1.5005(17) . ? C4 H41 0.991(19) . ? C4 H42 0.93(2) . ? C4 H43 0.98(2) . ? C5 C6 1.3895(18) . ? C5 C10 1.3956(17) . ? C6 C7 1.3864(18) . ? C6 H6 0.980(15) . ? C7 C8 1.385(2) . ? C7 H7 0.996(17) . ? C8 C9 1.377(2) . ? C8 H8 0.975(17) . ? C9 C10 1.384(2) . ? C9 H9 0.975(17) . ? C10 H10 0.977(17) . ? C11 C16 1.3907(16) . ? C11 C12 1.3969(16) . ? C12 C13 1.3810(17) . ? C12 H12 0.975(14) . ? C13 C14 1.3934(16) . ? C13 H13 0.966(14) . ? C14 C15 1.3909(16) . ? C15 C16 1.3873(17) . ? C15 H15 0.974(14) . ? C16 H16 0.968(14) . ? C17 H171 0.964(19) . ? C17 H172 0.95(2) . ? C17 H173 0.95(2) . ? C18 H181 0.992(15) . ? C18 H182 0.972(17) . ? C18 H183 1.017(17) . ? 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 C14 O2 C18 117.03(10) . . ? N2 N1 C11 112.87(10) . . ? N2 N1 H1 123(7) . . ? C11 N1 H1 124(7) . . ? N1 N2 C1 119.46(10) . . ? C2 N3 C17 125.62(12) . . ? C2 N3 H3 115.8(11) . . ? C17 N3 H3 118.6(11) . . ? N2 C1 C2 125.86(11) . . ? N2 C1 C3 111.67(10) . . ? C2 C1 C3 122.46(11) . . ? N3 C2 C1 119.07(11) . . ? N3 C2 C4 117.78(11) . . ? C1 C2 C4 123.07(11) . . ? O1 C3 C1 123.28(11) . . ? O1 C3 C5 117.56(11) . . ? C1 C3 C5 119.15(10) . . ? C2 C4 H41 111.1(10) . . ? C2 C4 H42 110.5(13) . . ? H41 C4 H42 107.9(16) . . ? C2 C4 H43 111.8(13) . . ? H41 C4 H43 109.9(15) . . ? H42 C4 H43 105.4(18) . . ? C6 C5 C10 119.00(12) . . ? C6 C5 C3 122.10(10) . . ? C10 C5 C3 118.50(11) . . ? C7 C6 C5 120.53(12) . . ? C7 C6 H6 119.7(8) . . ? C5 C6 H6 119.7(8) . . ? C8 C7 C6 119.81(14) . . ? C8 C7 H7 119.6(10) . . ? C6 C7 H7 120.6(10) . . ? C9 C8 C7 120.14(14) . . ? C9 C8 H8 122.4(10) . . ? C7 C8 H8 117.4(10) . . ? C8 C9 C10 120.29(13) . . ? C8 C9 H9 121.5(10) . . ? C10 C9 H9 118.2(10) . . ? C9 C10 C5 120.21(14) . . ? C9 C10 H10 123.8(9) . . ? C5 C10 H10 116.0(9) . . ? C16 C11 C12 119.17(11) . . ? C16 C11 N1 123.22(10) . . ? C12 C11 N1 117.56(10) . . ? C13 C12 C11 120.15(11) . . ? C13 C12 H12 121.5(8) . . ? C11 C12 H12 118.4(8) . . ? C12 C13 C14 120.38(11) . . ? C12 C13 H13 120.9(8) . . ? C14 C13 H13 118.8(8) . . ? O2 C14 C15 124.40(10) . . ? O2 C14 C13 115.76(10) . . ? C15 C14 C13 119.84(11) . . ? C16 C15 C14 119.56(11) . . ? C16 C15 H15 120.9(8) . . ? C14 C15 H15 119.5(8) . . ? C15 C16 C11 120.88(11) . . ? C15 C16 H16 119.4(8) . . ? C11 C16 H16 119.7(8) . . ? N3 C17 H171 111.0(11) . . ? N3 C17 H172 112.4(11) . . ? H171 C17 H172 107.1(15) . . ? N3 C17 H173 105.6(12) . . ? H171 C17 H173 109.3(16) . . ? H172 C17 H173 111.5(17) . . ? O2 C18 H181 110.3(9) . . ? O2 C18 H182 106.1(10) . . ? H181 C18 H182 110.2(13) . . ? O2 C18 H183 111.9(9) . . ? H181 C18 H183 108.2(13) . . ? H182 C18 H183 110.1(13) . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.99 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.216 _refine_diff_density_min -0.175 _refine_diff_density_rms 0.034 ###END=== data_(8) _database_code_depnum_ccdc_archive 'CCDC 633164' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C21 H25 N3 O' _chemical_formula_sum 'C21 H25 N3 O' _chemical_formula_weight 335.44 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 'P 21/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 8.6915(2) _cell_length_b 17.1912(4) _cell_length_c 13.2188(3) _cell_angle_alpha 90.00 _cell_angle_beta 101.066(1) _cell_angle_gamma 90.00 _cell_volume 1938.39(8) _cell_formula_units_Z 4 _cell_measurement_temperature 295 _cell_measurement_reflns_used 17075 _cell_measurement_theta_min 4.40 _cell_measurement_theta_max 27.0 _exptl_crystal_description prismatic _exptl_crystal_colour yellow _exptl_crystal_size_max 0.42 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.38 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.149 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 720 _exptl_absorpt_coefficient_mu 0.072 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 295 _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_measurement_method '\f scans and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 21749 _diffrn_reflns_av_R_equivalents 0.0340 _diffrn_reflns_av_sigmaI/netI 0.0276 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 4.40 _diffrn_reflns_theta_max 27.00 _reflns_number_total 4180 _reflns_number_gt 3266 _reflns_threshold_expression I>2sigma(I) _computing_data_collection 'COLLECT (Nonius, 1997)' _computing_cell_refinement 'Denzo SMN (Otwinowski & Minor, 1997)' _computing_data_reduction 'Denzo SMN (Otwinowski & Minor, 1997)' _computing_structure_solution 'SIR97 (Altomare et al., 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEPIII (Burnett & Johnson, 1996)' _computing_publication_material ; SHELXL-97 (Sheldrick, 1997), PARST (Nardelli, 1995) ; _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^)+(0.0707P)^2^+0.4030P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4180 _refine_ls_number_parameters 329 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0674 _refine_ls_R_factor_gt 0.0519 _refine_ls_wR_factor_ref 0.1487 _refine_ls_wR_factor_gt 0.1335 _refine_ls_goodness_of_fit_ref 1.014 _refine_ls_restrained_S_all 1.014 _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 O1 O 0.34210(18) 0.12608(8) 0.34658(10) 0.0838(4) Uani 1 1 d . . . N1 N 0.64516(14) 0.19802(7) 0.11266(9) 0.0510(3) Uani 1 1 d . . . H1 H 0.59(3) 0.245(14) 0.084(15) 0.061 Uiso 0.09(3) 1 d P . . N2 N 0.59031(14) 0.14974(7) 0.17078(8) 0.0479(3) Uani 1 1 d . . . N3 N 0.42206(17) 0.29223(8) 0.12717(12) 0.0652(4) Uani 1 1 d . . . H3 H 0.515(3) 0.2788(15) 0.1043(17) 0.078 Uiso 0.91(3) 1 d P . . C1 C 0.45862(17) 0.16953(8) 0.20809(10) 0.0491(3) Uani 1 1 d . . . C2 C 0.36939(17) 0.23914(9) 0.18379(11) 0.0534(4) Uani 1 1 d . . . C3 C 0.42060(19) 0.11176(9) 0.28076(11) 0.0559(4) Uani 1 1 d . . . C4 C 0.2155(2) 0.25193(13) 0.21591(15) 0.0656(4) Uani 1 1 d . . . C5 C 0.48632(17) 0.03111(9) 0.27857(12) 0.0547(4) Uani 1 1 d . . . C6 C 0.4740(2) -0.01184(10) 0.18861(15) 0.0651(4) Uani 1 1 d . . . C7 C 0.5258(3) -0.08859(11) 0.1927(2) 0.0807(6) Uani 1 1 d . . . C8 C 0.5945(2) -0.12103(13) 0.2857(3) 0.0920(8) Uani 1 1 d . . . C9 C 0.6070(2) -0.07875(14) 0.3754(2) 0.0902(7) Uani 1 1 d . . . C10 C 0.5515(2) -0.00343(12) 0.37174(16) 0.0709(5) Uani 1 1 d . . . C11 C 0.78106(16) 0.17220(8) 0.07788(10) 0.0474(3) Uani 1 1 d . . . C12 C 0.83017(18) 0.21823(9) 0.00368(11) 0.0538(3) Uani 1 1 d . . . C13 C 0.96117(18) 0.19810(10) -0.03472(12) 0.0582(4) Uani 1 1 d . . . C14 C 1.04864(18) 0.13234(10) -0.00030(11) 0.0572(4) Uani 1 1 d . . . C15 C 0.9991(2) 0.08723(10) 0.07493(13) 0.0608(4) Uani 1 1 d . . . C16 C 0.86726(19) 0.10610(9) 0.11378(12) 0.0559(4) Uani 1 1 d . . . C17 C 1.1927(2) 0.11212(16) -0.04215(18) 0.0756(5) Uani 1 1 d . . . C18 C 0.3516(2) 0.36758(12) 0.0915(2) 0.0859(6) Uani 1 1 d . . . C19 C 0.3953(5) 0.42994(16) 0.1790(3) 0.1211(11) Uani 1 1 d . . . C20 C 0.4140(3) 0.39016(16) -0.0033(2) 0.1028(8) Uani 1 1 d . . . C21 C 0.3694(5) 0.3338(2) -0.0893(3) 0.1281(11) Uani 1 1 d . . . H41 H 0.141(3) 0.2758(16) 0.163(2) 0.115(8) Uiso 1 1 d . . . H42 H 0.221(3) 0.2876(15) 0.2730(19) 0.106(7) Uiso 1 1 d . . . H43 H 0.163(3) 0.2028(17) 0.2294(19) 0.121(9) Uiso 1 1 d . . . H6 H 0.429(2) 0.0123(11) 0.1257(15) 0.075(5) Uiso 1 1 d . . . H7 H 0.513(3) -0.1153(13) 0.1334(17) 0.090(7) Uiso 1 1 d . . . H8 H 0.632(3) -0.1721(16) 0.2814(19) 0.111(8) Uiso 1 1 d . . . H9 H 0.651(3) -0.1004(15) 0.450(2) 0.117(8) Uiso 1 1 d . . . H10 H 0.559(3) 0.0265(13) 0.4377(18) 0.097(7) Uiso 1 1 d . . . H12 H 0.768(2) 0.2641(11) -0.0222(13) 0.068(5) Uiso 1 1 d . . . H13 H 0.995(2) 0.2325(11) -0.0833(14) 0.075(5) Uiso 1 1 d . . . H15 H 1.057(2) 0.0419(12) 0.1028(15) 0.083(6) Uiso 1 1 d . . . H16 H 0.830(2) 0.0752(11) 0.1638(14) 0.071(5) Uiso 1 1 d . . . H171 H 1.213(4) 0.058(2) -0.038(2) 0.145(11) Uiso 1 1 d . . . H172 H 1.290(4) 0.1330(19) 0.000(3) 0.154(11) Uiso 1 1 d . . . H173 H 1.177(4) 0.1313(18) -0.110(3) 0.148(12) Uiso 1 1 d . . . H18 H 0.239(3) 0.3570(12) 0.0701(16) 0.086(6) Uiso 1 1 d . . . H191 H 0.355(4) 0.477(2) 0.153(2) 0.148(11) Uiso 1 1 d . . . H192 H 0.353(4) 0.411(2) 0.239(3) 0.159(14) Uiso 1 1 d . . . H193 H 0.514(3) 0.4383(15) 0.1828(19) 0.114(9) Uiso 1 1 d . . . H201 H 0.537(4) 0.3965(17) 0.022(2) 0.128(9) Uiso 1 1 d . . . H202 H 0.362(4) 0.4476(19) -0.020(2) 0.146(10) Uiso 1 1 d . . . H221 H 0.413(4) 0.277(2) -0.078(2) 0.148(11) Uiso 1 1 d . . . H222 H 0.246(5) 0.330(2) -0.094(3) 0.188(16) Uiso 1 1 d . . . H223 H 0.394(5) 0.354(3) -0.156(3) 0.196(16) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.1182(11) 0.0736(8) 0.0751(8) 0.0018(6) 0.0572(8) 0.0099(7) N1 0.0581(7) 0.0434(6) 0.0541(6) 0.0050(5) 0.0176(5) 0.0040(5) N2 0.0560(6) 0.0434(6) 0.0457(6) -0.0008(5) 0.0132(5) 0.0003(5) N3 0.0612(8) 0.0516(8) 0.0861(10) 0.0132(7) 0.0226(7) 0.0146(6) C1 0.0561(8) 0.0447(7) 0.0479(7) -0.0034(5) 0.0140(6) 0.0009(6) C2 0.0538(8) 0.0519(8) 0.0545(8) -0.0075(6) 0.0101(6) 0.0028(6) C3 0.0662(9) 0.0536(8) 0.0520(8) -0.0038(6) 0.0214(7) -0.0030(7) C4 0.0553(9) 0.0720(11) 0.0706(10) -0.0088(9) 0.0148(8) 0.0069(8) C5 0.0555(8) 0.0510(8) 0.0622(8) 0.0072(6) 0.0225(6) -0.0046(6) C6 0.0766(11) 0.0516(9) 0.0733(10) 0.0025(8) 0.0296(9) 0.0026(8) C7 0.0845(13) 0.0542(10) 0.1172(17) -0.0046(11) 0.0542(12) -0.0031(9) C8 0.0704(12) 0.0556(11) 0.161(2) 0.0353(14) 0.0507(14) 0.0106(9) C9 0.0705(12) 0.0812(14) 0.1198(18) 0.0441(14) 0.0200(12) 0.0022(10) C10 0.0649(10) 0.0738(11) 0.0751(11) 0.0204(9) 0.0163(8) -0.0083(8) C11 0.0544(7) 0.0419(7) 0.0468(7) -0.0016(5) 0.0122(6) 0.0014(6) C12 0.0601(8) 0.0495(8) 0.0529(8) 0.0064(6) 0.0134(6) 0.0022(7) C13 0.0615(9) 0.0647(10) 0.0510(8) 0.0032(7) 0.0174(7) -0.0041(7) C14 0.0567(8) 0.0641(9) 0.0520(8) -0.0110(7) 0.0138(6) -0.0020(7) C15 0.0675(9) 0.0526(9) 0.0642(9) -0.0010(7) 0.0176(7) 0.0124(7) C16 0.0702(9) 0.0452(8) 0.0560(8) 0.0053(6) 0.0217(7) 0.0076(7) C17 0.0640(11) 0.0921(15) 0.0756(12) -0.0138(11) 0.0254(9) 0.0047(10) C18 0.0650(11) 0.0647(12) 0.1294(18) 0.0267(11) 0.0223(11) 0.0224(9) C19 0.142(3) 0.0590(14) 0.167(3) -0.0076(16) 0.042(2) 0.0276(16) C20 0.0856(15) 0.0847(16) 0.134(2) 0.0485(16) 0.0112(14) 0.0102(12) C21 0.156(3) 0.124(3) 0.0903(19) 0.0307(18) -0.0099(19) 0.000(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C3 1.2292(18) . ? N1 N2 1.2834(16) . ? N1 C11 1.4185(18) . ? N1 H1 1.0(3) . ? N2 C1 1.3732(18) . ? N3 C2 1.317(2) . ? N3 C18 1.471(2) . ? N3 H3 0.94(3) . ? C1 C2 1.429(2) . ? C1 C3 1.463(2) . ? C2 C4 1.495(2) . ? C3 C5 1.502(2) . ? C4 H41 0.95(3) . ? C4 H42 0.97(3) . ? C4 H43 0.99(3) . ? C5 C6 1.386(2) . ? C5 C10 1.387(2) . ? C6 C7 1.392(3) . ? C6 H6 0.944(19) . ? C7 C8 1.378(4) . ? C7 H7 0.90(2) . ? C8 C9 1.377(4) . ? C8 H8 0.94(3) . ? C9 C10 1.379(3) . ? C9 H9 1.05(3) . ? C10 H10 1.00(2) . ? C11 C12 1.390(2) . ? C11 C16 1.393(2) . ? C12 C13 1.377(2) . ? C12 H12 0.981(19) . ? C13 C14 1.389(2) . ? C13 H13 0.961(19) . ? C14 C15 1.393(2) . ? C14 C17 1.503(2) . ? C15 C16 1.381(2) . ? C15 H15 0.96(2) . ? C16 H16 0.952(19) . ? C17 H171 0.94(3) . ? C17 H172 0.99(4) . ? C17 H173 0.95(3) . ? C18 C20 1.508(4) . ? C18 C19 1.569(4) . ? C18 H18 0.99(2) . ? C19 H191 0.92(4) . ? C19 H192 0.99(4) . ? C19 H193 1.03(3) . ? C20 C21 1.488(5) . ? C20 H201 1.06(3) . ? C20 H202 1.09(3) . ? C21 H221 1.04(4) . ? C21 H222 1.06(4) . ? C21 H223 1.00(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 N2 N1 C11 114.82(12) . . ? N2 N1 H1 123(10) . . ? C11 N1 H1 122(10) . . ? N1 N2 C1 119.06(12) . . ? C2 N3 C18 128.58(15) . . ? C2 N3 H3 115.1(14) . . ? C18 N3 H3 116.2(14) . . ? N2 C1 C2 125.50(13) . . ? N2 C1 C3 112.12(12) . . ? C2 C1 C3 122.34(13) . . ? N3 C2 C1 118.38(13) . . ? N3 C2 C4 119.15(15) . . ? C1 C2 C4 122.40(15) . . ? O1 C3 C1 123.70(14) . . ? O1 C3 C5 117.60(14) . . ? C1 C3 C5 118.64(12) . . ? C2 C4 H41 112.0(15) . . ? C2 C4 H42 113.5(14) . . ? H41 C4 H42 103(2) . . ? C2 C4 H43 113.2(15) . . ? H41 C4 H43 103(2) . . ? H42 C4 H43 111(2) . . ? C6 C5 C10 119.01(17) . . ? C6 C5 C3 122.76(14) . . ? C10 C5 C3 118.05(15) . . ? C5 C6 C7 120.05(19) . . ? C5 C6 H6 118.2(12) . . ? C7 C6 H6 121.7(12) . . ? C8 C7 C6 120.0(2) . . ? C8 C7 H7 122.2(15) . . ? C6 C7 H7 117.9(15) . . ? C9 C8 C7 120.3(2) . . ? C9 C8 H8 124.9(15) . . ? C7 C8 H8 114.8(15) . . ? C8 C9 C10 119.8(2) . . ? C8 C9 H9 125.0(14) . . ? C10 C9 H9 115.1(15) . . ? C9 C10 C5 120.9(2) . . ? C9 C10 H10 119.2(13) . . ? C5 C10 H10 119.9(14) . . ? C12 C11 C16 119.14(13) . . ? C12 C11 N1 115.99(12) . . ? C16 C11 N1 124.86(13) . . ? C13 C12 C11 120.32(14) . . ? C13 C12 H12 121.0(10) . . ? C11 C12 H12 118.6(10) . . ? C12 C13 C14 121.53(15) . . ? C12 C13 H13 118.4(11) . . ? C14 C13 H13 119.9(11) . . ? C13 C14 C15 117.52(14) . . ? C13 C14 C17 120.63(17) . . ? C15 C14 C17 121.84(17) . . ? C16 C15 C14 121.81(15) . . ? C16 C15 H15 117.4(12) . . ? C14 C15 H15 120.7(12) . . ? C15 C16 C11 119.68(14) . . ? C15 C16 H16 123.0(11) . . ? C11 C16 H16 117.3(11) . . ? C14 C17 H171 111.5(18) . . ? C14 C17 H172 113.3(19) . . ? H171 C17 H172 101(3) . . ? C14 C17 H173 107.2(19) . . ? H171 C17 H173 113(3) . . ? H172 C17 H173 111(3) . . ? N3 C18 C20 107.40(18) . . ? N3 C18 C19 109.8(2) . . ? C20 C18 C19 111.2(2) . . ? N3 C18 H18 105.1(12) . . ? C20 C18 H18 107.9(12) . . ? C19 C18 H18 115.1(12) . . ? C18 C19 H191 107(2) . . ? C18 C19 H192 106(2) . . ? H191 C19 H192 115(3) . . ? C18 C19 H193 103.3(15) . . ? H191 C19 H193 101(3) . . ? H192 C19 H193 122(3) . . ? C21 C20 C18 112.6(3) . . ? C21 C20 H201 113.6(15) . . ? C18 C20 H201 105.8(15) . . ? C21 C20 H202 113.4(16) . . ? C18 C20 H202 101.7(15) . . ? H201 C20 H202 109(2) . . ? C20 C21 H221 117.8(18) . . ? C20 C21 H222 101(2) . . ? H221 C21 H222 107(3) . . ? C20 C21 H223 112(2) . . ? H221 C21 H223 108(3) . . ? H222 C21 H223 110(3) . . ? _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 27.00 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.340 _refine_diff_density_min -0.161 _refine_diff_density_rms 0.028 ###END=== data_(9) _database_code_depnum_ccdc_archive 'CCDC 633165' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C21 H25 N3 O' _chemical_formula_sum 'C21 H25 N3 O' _chemical_formula_weight 335.44 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' _cell_length_a 8.5205(2) _cell_length_b 12.6244(3) _cell_length_c 18.1441(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1951.69(8) _cell_formula_units_Z 4 _cell_measurement_temperature 295 _cell_measurement_reflns_used 8647 _cell_measurement_theta_min 3.93 _cell_measurement_theta_max 27.00 _exptl_crystal_description prismatic _exptl_crystal_colour yellow _exptl_crystal_size_max 0.52 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.19 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.142 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 720 _exptl_absorpt_coefficient_mu 0.071 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 295 _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_measurement_method '\f scans and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 15185 _diffrn_reflns_av_R_equivalents 0.0360 _diffrn_reflns_av_sigmaI/netI 0.0374 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 3.93 _diffrn_reflns_theta_max 27.00 _reflns_number_total 4208 _reflns_number_gt 3301 _reflns_threshold_expression I>2sigma(I) _computing_data_collection 'COLLECT (Nonius, 1997)' _computing_cell_refinement 'Denzo SMN (Otwinowski & Minor, 1997)' _computing_data_reduction 'Denzo SMN (Otwinowski & Minor, 1997)' _computing_structure_solution 'SIR97 (Altomare et al., 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEPIII (Burnett & Johnson, 1996)' _computing_publication_material ; SHELXL-97 (Sheldrick, 1997), PARST (Nardelli, 1995) ; _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^)+(0.0740P)^2^+0.0839P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.095(7) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.4(17) _refine_ls_number_reflns 4208 _refine_ls_number_parameters 274 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0605 _refine_ls_R_factor_gt 0.0440 _refine_ls_wR_factor_ref 0.1213 _refine_ls_wR_factor_gt 0.1106 _refine_ls_goodness_of_fit_ref 1.019 _refine_ls_restrained_S_all 1.019 _refine_ls_shift/su_max 0.000 _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 0.2665(2) 0.47260(12) -0.03013(9) 0.0887(6) Uani 1 1 d . . . N1 N 0.60134(17) 0.34019(11) 0.14732(8) 0.0480(3) Uani 1 1 d D . . H1 H 0.563(14) 0.275(5) 0.162(6) 0.058 Uiso 0.17(3) 1 d PD . . N2 N 0.54204(16) 0.41118(10) 0.10484(7) 0.0450(3) Uani 1 1 d . . . N3 N 0.37003(17) 0.21759(10) 0.11368(8) 0.0478(3) Uani 1 1 d D . . H3 H 0.461(3) 0.2334(19) 0.1388(12) 0.057 Uiso 0.83(3) 1 d PD . . C1 C 0.4012(2) 0.39254(12) 0.07022(8) 0.0449(4) Uani 1 1 d . . . C2 C 0.31501(19) 0.29533(12) 0.07285(8) 0.0450(4) Uani 1 1 d . . . C3 C 0.3572(2) 0.48096(13) 0.02191(10) 0.0533(4) Uani 1 1 d . . . C4 C 0.1643(2) 0.28275(16) 0.03111(13) 0.0678(5) Uani 1 1 d . . . H4A H 0.1866 0.2754 -0.0205 0.102 Uiso 1 1 calc R . . H4B H 0.0996 0.3440 0.0388 0.102 Uiso 1 1 calc R . . H4C H 0.1102 0.2208 0.0483 0.102 Uiso 1 1 calc R . . C5 C 0.4300(2) 0.58760(12) 0.03605(10) 0.0518(4) Uani 1 1 d . . . C6 C 0.4416(3) 0.63188(14) 0.10531(12) 0.0634(5) Uani 1 1 d . . . C7 C 0.5027(3) 0.73298(16) 0.11486(16) 0.0780(6) Uani 1 1 d . . . C8 C 0.5572(3) 0.78834(18) 0.05470(17) 0.0825(7) Uani 1 1 d . . . C9 C 0.5464(3) 0.74571(19) -0.01396(17) 0.0854(8) Uani 1 1 d . . . C10 C 0.4803(3) 0.64589(17) -0.02453(13) 0.0692(5) Uani 1 1 d . . . C11 C 0.7525(2) 0.36644(13) 0.17472(9) 0.0467(4) Uani 1 1 d . . . C12 C 0.8155(2) 0.30006(16) 0.22781(11) 0.0591(5) Uani 1 1 d . . . C13 C 0.9642(2) 0.31944(18) 0.25650(11) 0.0648(5) Uani 1 1 d . . . C14 C 1.0537(2) 0.40347(18) 0.23209(10) 0.0615(5) Uani 1 1 d . . . C15 C 0.9898(2) 0.46932(19) 0.17865(11) 0.0650(5) Uani 1 1 d . . . C16 C 0.8415(2) 0.45277(16) 0.15027(10) 0.0553(4) Uani 1 1 d . . . C17 C 1.2150(3) 0.4235(3) 0.26401(13) 0.0911(8) Uani 1 1 d . . . H17A H 1.2135 0.4093 0.3160 0.137 Uiso 1 1 calc R . . H17B H 1.2439 0.4960 0.2558 0.137 Uiso 1 1 calc R . . H17C H 1.2899 0.3778 0.2405 0.137 Uiso 1 1 calc R . . C18 C 0.3162(2) 0.10639(13) 0.12523(9) 0.0525(4) Uani 1 1 d . . . C19 C 0.3173(3) 0.04523(15) 0.05269(11) 0.0673(5) Uani 1 1 d . . . H19A H 0.2378 0.0730 0.0206 0.101 Uiso 1 1 calc R . . H19B H 0.2967 -0.0283 0.0622 0.101 Uiso 1 1 calc R . . H19C H 0.4182 0.0524 0.0296 0.101 Uiso 1 1 calc R . . C20 C 0.4412(3) 0.05836(18) 0.17485(15) 0.0865(8) Uani 1 1 d . . . H20A H 0.5415 0.0628 0.1510 0.130 Uiso 1 1 calc R . . H20B H 0.4163 -0.0146 0.1843 0.130 Uiso 1 1 calc R . . H20C H 0.4446 0.0965 0.2206 0.130 Uiso 1 1 calc R . . C21 C 0.1560(3) 0.1008(2) 0.16122(16) 0.0942(8) Uani 1 1 d . . . H21A H 0.1569 0.1411 0.2061 0.141 Uiso 1 1 calc R . . H21B H 0.1309 0.0283 0.1720 0.141 Uiso 1 1 calc R . . H21C H 0.0786 0.1295 0.1283 0.141 Uiso 1 1 calc R . . H6 H 0.405(3) 0.5936(19) 0.1479(13) 0.079(7) Uiso 1 1 d . . . H7 H 0.501(3) 0.7674(19) 0.1633(13) 0.079(7) Uiso 1 1 d . . . H8 H 0.599(3) 0.854(2) 0.0588(14) 0.094(8) Uiso 1 1 d . . . H9 H 0.569(3) 0.785(2) -0.0624(15) 0.098(8) Uiso 1 1 d . . . H10 H 0.468(3) 0.6146(19) -0.0783(14) 0.078(6) Uiso 1 1 d . . . H12 H 0.741(3) 0.2460(19) 0.2431(11) 0.076(7) Uiso 1 1 d . . . H13 H 1.016(3) 0.2739(18) 0.2897(12) 0.079(7) Uiso 1 1 d . . . H15 H 1.042(3) 0.538(2) 0.1592(13) 0.088(7) Uiso 1 1 d . . . H16 H 0.803(3) 0.5007(18) 0.1135(12) 0.072(6) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.1083(13) 0.0624(9) 0.0953(10) 0.0188(8) -0.0546(10) -0.0121(8) N1 0.0470(7) 0.0439(7) 0.0531(7) 0.0006(6) -0.0088(6) -0.0004(6) N2 0.0455(7) 0.0412(7) 0.0484(7) -0.0020(6) -0.0041(6) 0.0021(6) N3 0.0494(8) 0.0411(7) 0.0529(7) 0.0035(6) -0.0069(7) -0.0042(6) C1 0.0457(8) 0.0394(8) 0.0497(8) -0.0004(6) -0.0071(7) 0.0007(7) C2 0.0446(8) 0.0401(8) 0.0502(8) -0.0017(6) -0.0053(7) 0.0025(7) C3 0.0582(10) 0.0427(8) 0.0588(9) 0.0029(7) -0.0147(9) 0.0017(8) C4 0.0590(11) 0.0532(10) 0.0912(13) 0.0071(10) -0.0290(11) -0.0030(9) C5 0.0494(9) 0.0399(8) 0.0661(10) 0.0075(7) -0.0041(8) 0.0036(7) C6 0.0725(12) 0.0467(10) 0.0709(12) -0.0013(9) -0.0013(10) -0.0070(9) C7 0.0882(16) 0.0470(11) 0.0989(16) -0.0122(11) -0.0054(14) -0.0073(10) C8 0.0770(15) 0.0434(10) 0.127(2) 0.0013(13) 0.0047(15) -0.0107(10) C9 0.0887(17) 0.0625(13) 0.1049(19) 0.0254(13) 0.0106(14) -0.0142(12) C10 0.0742(13) 0.0577(11) 0.0757(13) 0.0120(10) 0.0010(11) 0.0011(10) C11 0.0433(8) 0.0495(9) 0.0474(8) -0.0077(7) -0.0049(7) 0.0031(7) C12 0.0546(10) 0.0553(10) 0.0674(10) 0.0014(8) -0.0107(9) 0.0031(9) C13 0.0555(11) 0.0750(13) 0.0640(11) -0.0056(10) -0.0153(9) 0.0165(10) C14 0.0446(9) 0.0865(14) 0.0534(10) -0.0195(9) -0.0045(8) 0.0021(10) C15 0.0553(10) 0.0809(14) 0.0588(11) -0.0115(10) -0.0004(9) -0.0138(10) C16 0.0525(10) 0.0631(10) 0.0503(9) -0.0017(8) -0.0057(8) -0.0073(9) C17 0.0532(11) 0.140(2) 0.0803(14) -0.0146(15) -0.0160(11) -0.0034(14) C18 0.0558(9) 0.0429(8) 0.0588(9) 0.0066(7) 0.0010(8) -0.0067(8) C19 0.0761(13) 0.0485(10) 0.0773(12) -0.0050(9) 0.0023(11) -0.0049(10) C20 0.1049(18) 0.0550(11) 0.0994(16) 0.0244(11) -0.0353(15) -0.0069(12) C21 0.0916(17) 0.0690(13) 0.122(2) 0.0080(13) 0.0521(16) -0.0087(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 O1 C3 1.225(2) . ? N1 N2 1.2855(19) . ? N1 C11 1.420(2) . ? N1 H1 0.93(3) . ? N2 C1 1.375(2) . ? N3 C2 1.316(2) . ? N3 C18 1.492(2) . ? N3 H3 0.92(3) . ? C1 C2 1.431(2) . ? C1 C3 1.468(2) . ? C2 C4 1.499(2) . ? C3 C5 1.504(2) . ? C4 H4A 0.9600 . ? C4 H4B 0.9600 . ? C4 H4C 0.9600 . ? C5 C6 1.379(3) . ? C5 C10 1.390(3) . ? C6 C7 1.389(3) . ? C6 H6 0.96(2) . ? C7 C8 1.377(4) . ? C7 H7 0.98(2) . ? C8 C9 1.360(4) . ? C8 H8 0.90(3) . ? C9 C10 1.393(3) . ? C9 H9 1.03(3) . ? C10 H10 1.06(2) . ? C11 C12 1.385(2) . ? C11 C16 1.400(3) . ? C12 C13 1.392(3) . ? C12 H12 0.97(2) . ? C13 C14 1.380(3) . ? C13 H13 0.94(2) . ? C14 C15 1.388(3) . ? C14 C17 1.512(3) . ? C15 C16 1.381(3) . ? C15 H15 1.04(3) . ? C16 H16 0.96(2) . ? C17 H17A 0.9600 . ? C17 H17B 0.9600 . ? C17 H17C 0.9600 . ? C18 C21 1.515(3) . ? C18 C20 1.521(3) . ? C18 C19 1.526(3) . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 0.9600 . ? C20 H20A 0.9600 . ? C20 H20B 0.9600 . ? C20 H20C 0.9600 . ? C21 H21A 0.9600 . ? C21 H21B 0.9600 . ? C21 H21C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N2 N1 C11 113.82(14) . . ? N2 N1 H1 131(8) . . ? C11 N1 H1 115(8) . . ? N1 N2 C1 119.85(13) . . ? C2 N3 C18 132.17(14) . . ? C2 N3 H3 114.6(15) . . ? C18 N3 H3 113.2(15) . . ? N2 C1 C2 125.41(14) . . ? N2 C1 C3 111.44(14) . . ? C2 C1 C3 122.76(14) . . ? N3 C2 C1 118.40(14) . . ? N3 C2 C4 120.70(14) . . ? C1 C2 C4 120.89(14) . . ? O1 C3 C1 123.77(16) . . ? O1 C3 C5 117.95(15) . . ? C1 C3 C5 118.26(14) . . ? C2 C4 H4A 109.5 . . ? C2 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? C2 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? C6 C5 C10 118.93(18) . . ? C6 C5 C3 123.21(17) . . ? C10 C5 C3 117.77(17) . . ? C5 C6 C7 120.9(2) . . ? C5 C6 H6 120.3(14) . . ? C7 C6 H6 118.8(14) . . ? C8 C7 C6 119.6(2) . . ? C8 C7 H7 119.4(14) . . ? C6 C7 H7 120.8(14) . . ? C9 C8 C7 120.2(2) . . ? C9 C8 H8 117.6(17) . . ? C7 C8 H8 122.2(17) . . ? C8 C9 C10 120.8(2) . . ? C8 C9 H9 125.2(15) . . ? C10 C9 H9 113.4(15) . . ? C5 C10 C9 119.6(2) . . ? C5 C10 H10 120.1(13) . . ? C9 C10 H10 120.2(13) . . ? C12 C11 C16 118.78(16) . . ? C12 C11 N1 116.99(16) . . ? C16 C11 N1 124.21(15) . . ? C11 C12 C13 120.4(2) . . ? C11 C12 H12 111.9(13) . . ? C13 C12 H12 127.5(13) . . ? C14 C13 C12 121.23(19) . . ? C14 C13 H13 114.6(15) . . ? C12 C13 H13 123.9(15) . . ? C13 C14 C15 117.91(17) . . ? C13 C14 C17 120.5(2) . . ? C15 C14 C17 121.6(2) . . ? C16 C15 C14 121.9(2) . . ? C16 C15 H15 113.2(14) . . ? C14 C15 H15 124.7(14) . . ? C15 C16 C11 119.71(18) . . ? C15 C16 H16 118.6(14) . . ? C11 C16 H16 121.7(13) . . ? C14 C17 H17A 109.5 . . ? C14 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C14 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? N3 C18 C21 112.43(16) . . ? N3 C18 C20 104.06(15) . . ? C21 C18 C20 110.93(19) . . ? N3 C18 C19 110.68(14) . . ? C21 C18 C19 110.73(18) . . ? C20 C18 C19 107.73(18) . . ? C18 C19 H19A 109.5 . . ? C18 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C18 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C18 C20 H20A 109.5 . . ? C18 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C18 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C18 C21 H21A 109.5 . . ? C18 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C18 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 27.00 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.152 _refine_diff_density_min -0.157 _refine_diff_density_rms 0.034 ###END===