data_18a _audit_creation_method SHELXTL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H19 N3 O' _chemical_formula_weight 269.34 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 6.6165(5) _cell_length_b 18.9916(11) _cell_length_c 11.2416(7) _cell_angle_alpha 90.00 _cell_angle_beta 93.587(4) _cell_angle_gamma 90.00 _cell_volume 1409.83(16) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 4288 _cell_measurement_theta_min 4.58 _cell_measurement_theta_max 69.66 _exptl_crystal_description Needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.03 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.269 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 576 _exptl_absorpt_coefficient_mu 0.645 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.779 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'Bruker MicroStar microfocus rotating anode' _diffrn_radiation_monochromator 'Helios multilayer optics' _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0.00 _diffrn_reflns_number 13195 _diffrn_reflns_av_R_equivalents 0.0537 _diffrn_reflns_av_sigmaI/netI 0.0400 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 4.58 _diffrn_reflns_theta_max 69.83 _reflns_number_total 2509 _reflns_number_gt 2131 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0731P)^2^+0.2266P] 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 SHELXL _refine_ls_extinction_coef 0.0053(8) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 2509 _refine_ls_number_parameters 258 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0522 _refine_ls_R_factor_gt 0.0439 _refine_ls_wR_factor_ref 0.1172 _refine_ls_wR_factor_gt 0.1123 _refine_ls_goodness_of_fit_ref 1.051 _refine_ls_restrained_S_all 1.051 _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 0.33540(17) 0.04908(5) 0.35994(9) 0.0282(3) Uani 1 1 d . . . N1 N 0.01622(19) 0.12811(6) 0.27741(11) 0.0246(3) Uani 1 1 d . . . N2 N -0.1425(2) 0.16266(6) 0.22242(11) 0.0262(3) Uani 1 1 d . . . N3 N -0.08678(19) 0.18010(6) 0.11597(11) 0.0258(3) Uani 1 1 d . . . C1 C -0.2406(3) 0.12593(10) 0.54603(16) 0.0376(4) Uani 1 1 d . . . H1A H -0.299(4) 0.1579(14) 0.601(2) 0.056(6) Uiso 1 1 d . . . H1B H -0.289(3) 0.0761(13) 0.5478(19) 0.050(6) Uiso 1 1 d . . . C2 C -0.0985(3) 0.14827(8) 0.47830(14) 0.0288(4) Uani 1 1 d . . . H2 H -0.057(3) 0.1965(12) 0.4808(18) 0.040(5) Uiso 1 1 d . . . C3 C 0.0126(2) 0.10054(8) 0.39954(13) 0.0257(3) Uani 1 1 d . . . H3 H -0.050(3) 0.0533(11) 0.3950(16) 0.030(5) Uiso 1 1 d . . . C4 C 0.2360(3) 0.09208(8) 0.44138(14) 0.0282(4) Uani 1 1 d . . . H4A H 0.247(3) 0.0678(10) 0.5192(18) 0.033(5) Uiso 1 1 d . . . H4B H 0.303(3) 0.1383(10) 0.4487(16) 0.031(5) Uiso 1 1 d . . . C5 C 0.3628(2) 0.08357(7) 0.24815(13) 0.0240(3) Uani 1 1 d . . . H5 H 0.477(3) 0.1185(9) 0.2611(15) 0.021(4) Uiso 1 1 d . . . C6 C 0.4170(2) 0.02679(7) 0.15821(13) 0.0253(3) Uani 1 1 d . . . H6 H 0.445(3) 0.0520(9) 0.0821(16) 0.025(4) Uiso 1 1 d . . . C7 C 0.2454(3) -0.02621(8) 0.13462(16) 0.0317(4) Uani 1 1 d . . . H7A H 0.216(3) -0.0521(11) 0.2110(19) 0.042(5) Uiso 1 1 d . . . H7B H 0.284(3) -0.0611(11) 0.0727(17) 0.034(5) Uiso 1 1 d . . . H7C H 0.127(3) -0.0015(11) 0.1017(19) 0.037(5) Uiso 1 1 d . . . C8 C 0.6137(3) -0.01016(8) 0.19993(16) 0.0323(4) Uani 1 1 d . . . H8A H 0.595(3) -0.0359(11) 0.279(2) 0.042(5) Uiso 1 1 d . . . H8B H 0.725(3) 0.0250(12) 0.2111(19) 0.044(6) Uiso 1 1 d . . . H8C H 0.656(3) -0.0459(12) 0.1393(19) 0.042(5) Uiso 1 1 d . . . C9 C 0.1733(2) 0.12306(7) 0.20717(13) 0.0234(3) Uani 1 1 d . . . C10 C 0.1069(2) 0.15726(7) 0.10300(13) 0.0236(3) Uani 1 1 d . . . C11 C 0.2103(2) 0.17369(7) -0.00555(13) 0.0232(3) Uani 1 1 d . . . C12 C 0.0998(2) 0.17669(7) -0.11578(13) 0.0261(3) Uani 1 1 d . . . H12 H -0.043(3) 0.1637(11) -0.1204(17) 0.038(5) Uiso 1 1 d . . . C13 C 0.1932(3) 0.19583(8) -0.21785(14) 0.0305(4) Uani 1 1 d . . . H13 H 0.116(3) 0.1970(12) -0.294(2) 0.048(6) Uiso 1 1 d . . . C14 C 0.3977(3) 0.21263(8) -0.21171(15) 0.0326(4) Uani 1 1 d . . . H14 H 0.464(3) 0.2283(11) -0.2875(19) 0.044(5) Uiso 1 1 d . . . C15 C 0.5091(3) 0.20924(8) -0.10305(15) 0.0295(4) Uani 1 1 d . . . H15 H 0.649(3) 0.2224(11) -0.0984(18) 0.041(5) Uiso 1 1 d . . . C16 C 0.4173(2) 0.18944(7) -0.00068(14) 0.0256(3) Uani 1 1 d . . . H16 H 0.496(3) 0.1877(9) 0.0731(17) 0.026(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 0.0358(7) 0.0252(6) 0.0237(6) 0.0027(4) 0.0022(4) 0.0051(4) N1 0.0286(7) 0.0208(6) 0.0244(7) 0.0013(5) 0.0016(5) -0.0008(4) N2 0.0261(7) 0.0242(6) 0.0282(7) 0.0027(5) 0.0019(5) -0.0001(5) N3 0.0273(7) 0.0227(6) 0.0275(7) 0.0015(5) 0.0030(5) -0.0004(5) C1 0.0422(11) 0.0349(9) 0.0369(9) 0.0030(7) 0.0110(7) 0.0052(7) C2 0.0359(9) 0.0235(8) 0.0273(8) 0.0007(6) 0.0033(6) 0.0007(6) C3 0.0324(9) 0.0220(7) 0.0226(8) 0.0029(5) 0.0025(6) -0.0029(6) C4 0.0325(9) 0.0269(8) 0.0251(8) -0.0008(6) 0.0013(6) 0.0017(6) C5 0.0279(8) 0.0207(7) 0.0235(8) 0.0023(5) 0.0014(6) 0.0010(5) C6 0.0299(9) 0.0197(7) 0.0264(8) 0.0006(6) 0.0019(6) 0.0018(5) C7 0.0345(10) 0.0246(8) 0.0361(9) -0.0044(6) 0.0014(7) -0.0018(6) C8 0.0347(10) 0.0247(8) 0.0370(9) -0.0028(6) -0.0028(7) 0.0060(6) C9 0.0262(8) 0.0180(7) 0.0259(7) -0.0014(5) 0.0021(6) -0.0021(5) C10 0.0255(8) 0.0182(7) 0.0268(8) -0.0013(5) -0.0006(6) 0.0007(5) C11 0.0285(8) 0.0149(6) 0.0262(8) 0.0005(5) 0.0019(6) 0.0015(5) C12 0.0303(9) 0.0189(7) 0.0290(8) -0.0002(5) 0.0003(6) 0.0027(5) C13 0.0413(10) 0.0245(8) 0.0255(8) 0.0009(6) 0.0007(7) 0.0070(6) C14 0.0448(11) 0.0224(8) 0.0317(9) 0.0042(6) 0.0111(7) 0.0054(6) C15 0.0319(10) 0.0211(7) 0.0363(9) 0.0010(6) 0.0089(6) 0.0001(6) C16 0.0294(8) 0.0195(7) 0.0278(8) -0.0015(5) 0.0015(6) 0.0004(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 C4 1.4190(19) . ? O1 C5 1.4387(18) . ? N1 C9 1.348(2) . ? N1 N2 1.3544(18) . ? N1 C3 1.4710(19) . ? N2 N3 1.3164(18) . ? N3 C10 1.369(2) . ? C1 C2 1.316(2) . ? C1 H1A 0.97(3) . ? C1 H1B 1.00(2) . ? C2 C3 1.492(2) . ? C2 H2 0.96(2) . ? C3 C4 1.532(2) . ? C3 H3 0.99(2) . ? C4 H4A 0.99(2) . ? C4 H4B 0.99(2) . ? C5 C9 1.508(2) . ? C5 C6 1.536(2) . ? C5 H5 1.012(18) . ? C6 C8 1.527(2) . ? C6 C7 1.528(2) . ? C6 H6 1.008(18) . ? C7 H7A 1.02(2) . ? C7 H7B 1.01(2) . ? C7 H7C 0.96(2) . ? C8 H8A 1.02(2) . ? C8 H8B 1.00(2) . ? C8 H8C 1.01(2) . ? C9 C10 1.386(2) . ? C10 C11 1.469(2) . ? C11 C16 1.400(2) . ? C11 C12 1.400(2) . ? C12 C13 1.386(2) . ? C12 H12 0.98(2) . ? C13 C14 1.387(3) . ? C13 H13 0.97(2) . ? C14 C15 1.388(2) . ? C14 H14 1.03(2) . ? C15 C16 1.386(2) . ? C15 H15 0.96(2) . ? C16 H16 0.951(19) . ? 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 C4 O1 C5 112.97(11) . . ? C9 N1 N2 111.81(12) . . ? C9 N1 C3 125.45(12) . . ? N2 N1 C3 122.74(13) . . ? N3 N2 N1 106.47(12) . . ? N2 N3 C10 109.52(12) . . ? C2 C1 H1A 119.9(15) . . ? C2 C1 H1B 124.0(13) . . ? H1A C1 H1B 116.1(19) . . ? C1 C2 C3 122.91(15) . . ? C1 C2 H2 120.5(13) . . ? C3 C2 H2 116.5(13) . . ? N1 C3 C2 112.02(12) . . ? N1 C3 C4 104.60(13) . . ? C2 C3 C4 112.53(13) . . ? N1 C3 H3 107.9(11) . . ? C2 C3 H3 111.2(11) . . ? C4 C3 H3 108.3(11) . . ? O1 C4 C3 109.86(12) . . ? O1 C4 H4A 107.1(11) . . ? C3 C4 H4A 109.5(11) . . ? O1 C4 H4B 110.0(11) . . ? C3 C4 H4B 110.7(11) . . ? H4A C4 H4B 109.6(15) . . ? O1 C5 C9 110.22(12) . . ? O1 C5 C6 107.61(11) . . ? C9 C5 C6 111.84(12) . . ? O1 C5 H5 107.9(10) . . ? C9 C5 H5 108.6(10) . . ? C6 C5 H5 110.5(10) . . ? C8 C6 C7 111.14(13) . . ? C8 C6 C5 110.51(12) . . ? C7 C6 C5 112.03(13) . . ? C8 C6 H6 106.2(10) . . ? C7 C6 H6 109.9(10) . . ? C5 C6 H6 106.8(10) . . ? C6 C7 H7A 110.6(12) . . ? C6 C7 H7B 109.6(11) . . ? H7A C7 H7B 109.7(16) . . ? C6 C7 H7C 108.7(12) . . ? H7A C7 H7C 111.3(17) . . ? H7B C7 H7C 106.8(16) . . ? C6 C8 H8A 109.8(12) . . ? C6 C8 H8B 109.9(13) . . ? H8A C8 H8B 109.7(17) . . ? C6 C8 H8C 111.5(12) . . ? H8A C8 H8C 108.3(17) . . ? H8B C8 H8C 107.5(17) . . ? N1 C9 C10 104.25(13) . . ? N1 C9 C5 120.89(13) . . ? C10 C9 C5 134.81(14) . . ? N3 C10 C9 107.94(14) . . ? N3 C10 C11 120.57(13) . . ? C9 C10 C11 131.41(14) . . ? C16 C11 C12 118.78(14) . . ? C16 C11 C10 121.22(13) . . ? C12 C11 C10 119.95(14) . . ? C13 C12 C11 120.54(15) . . ? C13 C12 H12 120.2(11) . . ? C11 C12 H12 119.2(12) . . ? C12 C13 C14 120.23(15) . . ? C12 C13 H13 120.0(14) . . ? C14 C13 H13 119.7(14) . . ? C13 C14 C15 119.71(16) . . ? C13 C14 H14 119.4(12) . . ? C15 C14 H14 120.9(12) . . ? C16 C15 C14 120.45(16) . . ? C16 C15 H15 119.9(13) . . ? C14 C15 H15 119.7(12) . . ? C15 C16 C11 120.27(14) . . ? C15 C16 H16 119.4(11) . . ? C11 C16 H16 120.3(11) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C9 N1 N2 N3 -0.12(15) . . . . ? C3 N1 N2 N3 179.51(12) . . . . ? N1 N2 N3 C10 -0.35(15) . . . . ? C9 N1 C3 C2 142.59(14) . . . . ? N2 N1 C3 C2 -36.99(18) . . . . ? C9 N1 C3 C4 20.43(18) . . . . ? N2 N1 C3 C4 -159.16(12) . . . . ? C1 C2 C3 N1 130.44(16) . . . . ? C1 C2 C3 C4 -112.03(18) . . . . ? C5 O1 C4 C3 71.36(16) . . . . ? N1 C3 C4 O1 -55.29(15) . . . . ? C2 C3 C4 O1 -177.13(12) . . . . ? C4 O1 C5 C9 -42.78(16) . . . . ? C4 O1 C5 C6 -164.98(12) . . . . ? O1 C5 C6 C8 -61.05(16) . . . . ? C9 C5 C6 C8 177.75(13) . . . . ? O1 C5 C6 C7 63.47(15) . . . . ? C9 C5 C6 C7 -57.73(16) . . . . ? N2 N1 C9 C10 0.53(15) . . . . ? C3 N1 C9 C10 -179.09(12) . . . . ? N2 N1 C9 C5 -177.07(12) . . . . ? C3 N1 C9 C5 3.3(2) . . . . ? O1 C5 C9 N1 6.05(18) . . . . ? C6 C5 C9 N1 125.73(14) . . . . ? O1 C5 C9 C10 -170.66(15) . . . . ? C6 C5 C9 C10 -51.0(2) . . . . ? N2 N3 C10 C9 0.69(16) . . . . ? N2 N3 C10 C11 -176.35(12) . . . . ? N1 C9 C10 N3 -0.72(15) . . . . ? C5 C9 C10 N3 176.37(14) . . . . ? N1 C9 C10 C11 175.88(14) . . . . ? C5 C9 C10 C11 -7.0(3) . . . . ? N3 C10 C11 C16 142.55(14) . . . . ? C9 C10 C11 C16 -33.7(2) . . . . ? N3 C10 C11 C12 -34.77(19) . . . . ? C9 C10 C11 C12 148.99(15) . . . . ? C16 C11 C12 C13 -0.9(2) . . . . ? C10 C11 C12 C13 176.51(13) . . . . ? C11 C12 C13 C14 -0.3(2) . . . . ? C12 C13 C14 C15 0.9(2) . . . . ? C13 C14 C15 C16 -0.2(2) . . . . ? C14 C15 C16 C11 -1.0(2) . . . . ? C12 C11 C16 C15 1.5(2) . . . . ? C10 C11 C16 C15 -175.82(13) . . . . ? _diffrn_measured_fraction_theta_max 0.942 _diffrn_reflns_theta_full 66.00 _diffrn_measured_fraction_theta_full 0.961 _refine_diff_density_max 0.222 _refine_diff_density_min -0.240 _refine_diff_density_rms 0.052 #===END data_18b _audit_creation_method SHELXTL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H19 N3 O' _chemical_formula_weight 269.34 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 6.6140(3) _cell_length_b 18.9847(6) _cell_length_c 11.2005(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.675(2) _cell_angle_gamma 90.00 _cell_volume 1406.29(9) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 7853 _cell_measurement_theta_min 4.58 _cell_measurement_theta_max 69.27 _exptl_crystal_description 'Rectangular parallelepiped' _exptl_crystal_colour colourless _exptl_crystal_size_max 0.21 _exptl_crystal_size_mid 0.07 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.272 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 576 _exptl_absorpt_coefficient_mu 0.647 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.850 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'Bruker MicroStar microfocus rotating anode' _diffrn_radiation_monochromator 'Helios multilayer optics' _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0.00 _diffrn_reflns_number 12452 _diffrn_reflns_av_R_equivalents 0.0268 _diffrn_reflns_av_sigmaI/netI 0.0220 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 4.58 _diffrn_reflns_theta_max 69.60 _reflns_number_total 2448 _reflns_number_gt 2286 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0402P)^2^+0.4031P] 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 SHELXL _refine_ls_extinction_coef 0.0013(3) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 2448 _refine_ls_number_parameters 258 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0322 _refine_ls_R_factor_gt 0.0300 _refine_ls_wR_factor_ref 0.0783 _refine_ls_wR_factor_gt 0.0769 _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 0.32603(11) 0.07080(4) 0.35293(6) 0.01904(19) Uani 1 1 d . . . N1 N 0.02945(14) 0.15429(4) 0.27188(8) 0.0185(2) Uani 1 1 d . . . N2 N -0.12621(14) 0.18776(5) 0.21683(8) 0.0211(2) Uani 1 1 d . . . N3 N -0.07491(14) 0.19553(4) 0.10437(8) 0.0199(2) Uani 1 1 d . . . C1 C -0.2490(2) 0.09528(8) 0.51935(11) 0.0327(3) Uani 1 1 d . . . H1A H -0.337(2) 0.0563(9) 0.5466(13) 0.040(4) Uiso 1 1 d . . . H1B H -0.267(2) 0.1399(9) 0.5552(14) 0.041(4) Uiso 1 1 d . . . C2 C -0.10932(18) 0.08542(6) 0.43894(10) 0.0234(3) Uani 1 1 d . . . H2 H -0.090(2) 0.0390(8) 0.4009(12) 0.032(4) Uiso 1 1 d . . . C3 C 0.03482(17) 0.14221(5) 0.40203(9) 0.0202(2) Uani 1 1 d . . . H3 H 0.0005(19) 0.1870(7) 0.4403(11) 0.019(3) Uiso 1 1 d . . . C4 C 0.25462(17) 0.12374(6) 0.43204(9) 0.0209(2) Uani 1 1 d . . . H4A H 0.2595(18) 0.1043(6) 0.5124(11) 0.017(3) Uiso 1 1 d . . . H4B H 0.3422(19) 0.1662(7) 0.4264(11) 0.021(3) Uiso 1 1 d . . . C5 C 0.36388(16) 0.09928(5) 0.23661(9) 0.0173(2) Uani 1 1 d . . . H5 H 0.4824(18) 0.1337(6) 0.2398(10) 0.011(3) Uiso 1 1 d . . . C6 C 0.41391(16) 0.03776(5) 0.15304(9) 0.0186(2) Uani 1 1 d . . . H6 H 0.4383(18) 0.0584(6) 0.0734(11) 0.017(3) Uiso 1 1 d . . . C7 C 0.24120(19) -0.01542(6) 0.14348(10) 0.0244(3) Uani 1 1 d . . . H7A H 0.212(2) -0.0386(7) 0.2210(13) 0.030(3) Uiso 1 1 d . . . H7B H 0.273(2) -0.0528(7) 0.0851(12) 0.030(3) Uiso 1 1 d . . . H7C H 0.119(2) 0.0069(8) 0.1151(13) 0.036(4) Uiso 1 1 d . . . C8 C 0.61167(18) 0.00297(6) 0.19248(10) 0.0243(3) Uani 1 1 d . . . H8A H 0.649(2) -0.0355(8) 0.1378(12) 0.031(3) Uiso 1 1 d . . . H8B H 0.600(2) -0.0167(7) 0.2739(13) 0.029(3) Uiso 1 1 d . . . H8C H 0.726(2) 0.0381(8) 0.1949(12) 0.032(4) Uiso 1 1 d . . . C9 C 0.18032(16) 0.14009(5) 0.19536(9) 0.0170(2) Uani 1 1 d . . . C10 C 0.11336(16) 0.16765(5) 0.08767(9) 0.0172(2) Uani 1 1 d . . . C11 C 0.21591(17) 0.17399(5) -0.02780(9) 0.0182(2) Uani 1 1 d . . . C12 C 0.10455(19) 0.16857(5) -0.13453(10) 0.0223(3) Uani 1 1 d . . . H12 H -0.037(2) 0.1573(7) -0.1286(12) 0.026(3) Uiso 1 1 d . . . C13 C 0.1969(2) 0.17893(6) -0.24340(10) 0.0288(3) Uani 1 1 d . . . H13 H 0.117(2) 0.1751(8) -0.3166(13) 0.039(4) Uiso 1 1 d . . . C14 C 0.4003(2) 0.19516(6) -0.24806(11) 0.0310(3) Uani 1 1 d . . . H14 H 0.466(2) 0.2037(8) -0.3250(14) 0.038(4) Uiso 1 1 d . . . C15 C 0.5134(2) 0.20003(6) -0.14285(11) 0.0267(3) Uani 1 1 d . . . H15 H 0.652(2) 0.2128(7) -0.1447(12) 0.031(4) Uiso 1 1 d . . . C16 C 0.42215(17) 0.18910(5) -0.03347(10) 0.0203(2) Uani 1 1 d . . . H16 H 0.502(2) 0.1932(7) 0.0400(11) 0.022(3) 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 0.0238(4) 0.0179(4) 0.0154(4) 0.0000(3) 0.0006(3) 0.0019(3) N1 0.0200(5) 0.0159(4) 0.0197(5) 0.0006(3) 0.0012(3) 0.0004(3) N2 0.0190(5) 0.0198(5) 0.0246(5) 0.0012(3) 0.0008(4) 0.0018(3) N3 0.0194(5) 0.0184(4) 0.0220(5) 0.0005(3) 0.0011(4) 0.0004(3) C1 0.0270(7) 0.0409(7) 0.0302(7) 0.0088(5) 0.0036(5) -0.0008(5) C2 0.0241(7) 0.0247(6) 0.0214(5) 0.0033(4) -0.0020(4) -0.0021(4) C3 0.0250(6) 0.0181(5) 0.0175(5) -0.0015(4) 0.0033(4) 0.0006(4) C4 0.0243(6) 0.0211(5) 0.0174(5) -0.0034(4) 0.0009(4) -0.0011(4) C5 0.0188(6) 0.0162(5) 0.0169(5) 0.0009(4) 0.0004(4) -0.0002(4) C6 0.0214(6) 0.0170(5) 0.0173(5) 0.0000(4) 0.0005(4) 0.0026(4) C7 0.0280(7) 0.0187(5) 0.0265(6) -0.0042(4) -0.0010(5) -0.0007(4) C8 0.0263(7) 0.0216(5) 0.0248(6) -0.0027(4) -0.0021(5) 0.0063(5) C9 0.0188(6) 0.0134(5) 0.0188(5) -0.0018(4) 0.0018(4) -0.0024(4) C10 0.0175(6) 0.0131(5) 0.0209(5) -0.0008(4) -0.0008(4) -0.0007(4) C11 0.0229(6) 0.0112(5) 0.0204(5) 0.0007(4) 0.0000(4) 0.0027(4) C12 0.0253(7) 0.0180(5) 0.0236(6) -0.0006(4) -0.0023(4) 0.0060(4) C13 0.0422(8) 0.0246(6) 0.0195(6) 0.0001(4) -0.0015(5) 0.0146(5) C14 0.0462(8) 0.0223(6) 0.0248(6) 0.0075(4) 0.0129(6) 0.0142(5) C15 0.0262(7) 0.0169(5) 0.0371(7) 0.0051(4) 0.0108(5) 0.0053(4) C16 0.0216(6) 0.0143(5) 0.0251(6) 0.0011(4) 0.0012(4) 0.0021(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 C4 1.4242(12) . ? O1 C5 1.4353(12) . ? N1 C9 1.3502(14) . ? N1 N2 1.3524(13) . ? N1 C3 1.4756(13) . ? N2 N3 1.3165(13) . ? N3 C10 1.3679(14) . ? C1 C2 1.3112(18) . ? C1 H1A 0.993(16) . ? C1 H1B 0.946(17) . ? C2 C3 1.5005(15) . ? C2 H2 0.987(15) . ? C3 C4 1.5290(16) . ? C3 H3 0.980(13) . ? C4 H4A 0.973(12) . ? C4 H4B 0.995(13) . ? C5 C9 1.5081(14) . ? C5 C6 1.5352(14) . ? C5 H5 1.021(12) . ? C6 C8 1.5260(15) . ? C6 C7 1.5274(15) . ? C6 H6 0.990(12) . ? C7 H7A 0.994(14) . ? C7 H7B 0.990(14) . ? C7 H7C 0.961(16) . ? C8 H8A 0.987(14) . ? C8 H8B 0.989(14) . ? C8 H8C 1.011(15) . ? C9 C10 1.3828(15) . ? C10 C11 1.4724(15) . ? C11 C16 1.3961(17) . ? C11 C12 1.4006(15) . ? C12 C13 1.3841(17) . ? C12 H12 0.963(15) . ? C13 C14 1.382(2) . ? C13 H13 0.974(16) . ? C14 C15 1.3912(18) . ? C14 H14 0.984(15) . ? C15 C16 1.3876(16) . ? C15 H15 0.950(15) . ? C16 H16 0.975(13) . ? 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 C4 O1 C5 111.19(8) . . ? C9 N1 N2 111.64(8) . . ? C9 N1 C3 125.92(9) . . ? N2 N1 C3 122.19(9) . . ? N3 N2 N1 106.59(8) . . ? N2 N3 C10 109.44(8) . . ? C2 C1 H1A 121.7(9) . . ? C2 C1 H1B 121.0(9) . . ? H1A C1 H1B 117.3(12) . . ? C1 C2 C3 122.80(11) . . ? C1 C2 H2 121.4(8) . . ? C3 C2 H2 115.7(8) . . ? N1 C3 C2 112.07(9) . . ? N1 C3 C4 105.34(8) . . ? C2 C3 C4 112.35(9) . . ? N1 C3 H3 107.1(7) . . ? C2 C3 H3 110.6(7) . . ? C4 C3 H3 109.1(7) . . ? O1 C4 C3 110.27(8) . . ? O1 C4 H4A 107.4(7) . . ? C3 C4 H4A 108.1(7) . . ? O1 C4 H4B 109.6(7) . . ? C3 C4 H4B 110.7(7) . . ? H4A C4 H4B 110.7(10) . . ? O1 C5 C9 108.86(8) . . ? O1 C5 C6 107.94(8) . . ? C9 C5 C6 112.49(8) . . ? O1 C5 H5 110.6(6) . . ? C9 C5 H5 107.3(6) . . ? C6 C5 H5 109.7(6) . . ? C8 C6 C7 111.84(9) . . ? C8 C6 C5 110.05(8) . . ? C7 C6 C5 112.29(9) . . ? C8 C6 H6 106.5(7) . . ? C7 C6 H6 109.2(7) . . ? C5 C6 H6 106.7(7) . . ? C6 C7 H7A 112.5(8) . . ? C6 C7 H7B 110.9(8) . . ? H7A C7 H7B 107.7(11) . . ? C6 C7 H7C 110.8(9) . . ? H7A C7 H7C 108.3(12) . . ? H7B C7 H7C 106.3(12) . . ? C6 C8 H8A 111.3(8) . . ? C6 C8 H8B 110.6(8) . . ? H8A C8 H8B 108.5(11) . . ? C6 C8 H8C 111.3(8) . . ? H8A C8 H8C 108.0(11) . . ? H8B C8 H8C 107.0(11) . . ? N1 C9 C10 104.28(9) . . ? N1 C9 C5 120.42(9) . . ? C10 C9 C5 135.23(9) . . ? N3 C10 C9 108.05(9) . . ? N3 C10 C11 121.20(9) . . ? C9 C10 C11 130.62(10) . . ? C16 C11 C12 118.72(10) . . ? C16 C11 C10 121.15(10) . . ? C12 C11 C10 120.05(10) . . ? C13 C12 C11 120.57(12) . . ? C13 C12 H12 122.1(8) . . ? C11 C12 H12 117.3(8) . . ? C14 C13 C12 120.32(11) . . ? C14 C13 H13 120.3(9) . . ? C12 C13 H13 119.4(9) . . ? C13 C14 C15 119.78(11) . . ? C13 C14 H14 120.7(9) . . ? C15 C14 H14 119.5(9) . . ? C16 C15 C14 120.19(12) . . ? C16 C15 H15 119.2(8) . . ? C14 C15 H15 120.6(8) . . ? C15 C16 C11 120.42(11) . . ? C15 C16 H16 119.8(8) . . ? C11 C16 H16 119.7(8) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C9 N1 N2 N3 -0.35(11) . . . . ? C3 N1 N2 N3 174.19(9) . . . . ? N1 N2 N3 C10 -0.46(11) . . . . ? C9 N1 C3 C2 -112.54(11) . . . . ? N2 N1 C3 C2 73.73(12) . . . . ? C9 N1 C3 C4 9.92(13) . . . . ? N2 N1 C3 C4 -163.81(9) . . . . ? C1 C2 C3 N1 -124.74(12) . . . . ? C1 C2 C3 C4 116.88(12) . . . . ? C5 O1 C4 C3 74.37(10) . . . . ? N1 C3 C4 O1 -49.10(10) . . . . ? C2 C3 C4 O1 73.18(11) . . . . ? C4 O1 C5 C9 -50.56(10) . . . . ? C4 O1 C5 C6 -172.94(8) . . . . ? O1 C5 C6 C8 -65.30(11) . . . . ? C9 C5 C6 C8 174.58(9) . . . . ? O1 C5 C6 C7 59.97(11) . . . . ? C9 C5 C6 C7 -60.14(11) . . . . ? N2 N1 C9 C10 0.98(11) . . . . ? C3 N1 C9 C10 -173.32(9) . . . . ? N2 N1 C9 C5 -176.56(8) . . . . ? C3 N1 C9 C5 9.15(15) . . . . ? O1 C5 C9 N1 10.35(12) . . . . ? C6 C5 C9 N1 129.93(10) . . . . ? O1 C5 C9 C10 -166.26(11) . . . . ? C6 C5 C9 C10 -46.67(16) . . . . ? N2 N3 C10 C9 1.08(11) . . . . ? N2 N3 C10 C11 -175.12(9) . . . . ? N1 C9 C10 N3 -1.22(11) . . . . ? C5 C9 C10 N3 175.76(10) . . . . ? N1 C9 C10 C11 174.49(10) . . . . ? C5 C9 C10 C11 -8.53(19) . . . . ? N3 C10 C11 C16 138.74(10) . . . . ? C9 C10 C11 C16 -36.49(16) . . . . ? N3 C10 C11 C12 -37.84(14) . . . . ? C9 C10 C11 C12 146.92(11) . . . . ? C16 C11 C12 C13 -0.83(15) . . . . ? C10 C11 C12 C13 175.83(9) . . . . ? C11 C12 C13 C14 -0.36(16) . . . . ? C12 C13 C14 C15 1.00(17) . . . . ? C13 C14 C15 C16 -0.43(16) . . . . ? C14 C15 C16 C11 -0.78(16) . . . . ? C12 C11 C16 C15 1.40(15) . . . . ? C10 C11 C16 C15 -175.23(9) . . . . ? _diffrn_measured_fraction_theta_max 0.929 _diffrn_reflns_theta_full 66.00 _diffrn_measured_fraction_theta_full 0.951 _refine_diff_density_max 0.216 _refine_diff_density_min -0.164 _refine_diff_density_rms 0.033 #===END data_27a _audit_creation_method SHELXTL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H21 N3 O' _chemical_formula_weight 295.38 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pbca loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 15.5492(8) _cell_length_b 10.0774(5) _cell_length_c 19.0625(10) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2987.0(3) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 9764 _cell_measurement_theta_min 2.84 _cell_measurement_theta_max 69.80 _exptl_crystal_description Plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.37 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.314 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1264 _exptl_absorpt_coefficient_mu 0.658 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.922 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'Bruker MicroStar microfocus rotating anode' _diffrn_radiation_monochromator 'Helios multilayer optics' _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0.00 _diffrn_reflns_number 27018 _diffrn_reflns_av_R_equivalents 0.0188 _diffrn_reflns_av_sigmaI/netI 0.0104 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 5.44 _diffrn_reflns_theta_max 69.69 _reflns_number_total 2712 _reflns_number_gt 2706 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0351P)^2^+1.4564P] 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 SHELXL _refine_ls_extinction_coef 0.00103(15) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 2712 _refine_ls_number_parameters 284 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0326 _refine_ls_R_factor_gt 0.0326 _refine_ls_wR_factor_ref 0.0792 _refine_ls_wR_factor_gt 0.0792 _refine_ls_goodness_of_fit_ref 1.069 _refine_ls_restrained_S_all 1.069 _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 0.15921(5) 0.17681(8) 0.20745(4) 0.0192(2) Uani 1 1 d . . . H1O H 0.1080(11) 0.1537(16) 0.2242(8) 0.034(4) Uiso 1 1 d . . . N1 N 0.10468(5) 0.44259(9) 0.30587(5) 0.0137(2) Uani 1 1 d . . . N2 N 0.03811(6) 0.52298(9) 0.31919(5) 0.0161(2) Uani 1 1 d . . . N3 N -0.00803(6) 0.52879(9) 0.26144(5) 0.0155(2) Uani 1 1 d . . . C1 C 0.15048(8) 0.43585(13) 0.49053(6) 0.0264(3) Uani 1 1 d . . . H1A H 0.1991(11) 0.4981(17) 0.4936(8) 0.038(4) Uiso 1 1 d . . . H1B H 0.1212(10) 0.4110(15) 0.5347(8) 0.032(4) Uiso 1 1 d . . . C2 C 0.12625(7) 0.38833(11) 0.42926(6) 0.0185(2) Uani 1 1 d . . . H2 H 0.0780(9) 0.3259(15) 0.4259(7) 0.027(4) Uiso 1 1 d . . . C3 C 0.17024(7) 0.42046(11) 0.36097(6) 0.0158(2) Uani 1 1 d . . . H3 H 0.2016(8) 0.5041(13) 0.3656(6) 0.015(3) Uiso 1 1 d . . . C4 C 0.23175(7) 0.31237(11) 0.33482(6) 0.0170(2) Uani 1 1 d . . . H4A H 0.2047(8) 0.2218(14) 0.3394(6) 0.017(3) Uiso 1 1 d . . . H4B H 0.2828(9) 0.3127(14) 0.3659(7) 0.026(4) Uiso 1 1 d . . . C5 C 0.25664(7) 0.33796(11) 0.25841(5) 0.0147(2) Uani 1 1 d . . . H5 H 0.2730(8) 0.4330(13) 0.2541(6) 0.014(3) Uiso 1 1 d . . . C6 C 0.33221(7) 0.25372(12) 0.23293(6) 0.0182(3) Uani 1 1 d . . . H6A H 0.3155(8) 0.1571(14) 0.2360(7) 0.017(3) Uiso 1 1 d . . . H6B H 0.3817(9) 0.2697(14) 0.2642(7) 0.023(3) Uiso 1 1 d . . . C7 C 0.35606(7) 0.28932(12) 0.15721(6) 0.0195(3) Uani 1 1 d . . . H7A H 0.3781(9) 0.3815(15) 0.1559(7) 0.023(3) Uiso 1 1 d . . . H7B H 0.4037(9) 0.2288(14) 0.1400(7) 0.024(3) Uiso 1 1 d . . . C8 C 0.27817(7) 0.27818(11) 0.10867(6) 0.0167(2) Uani 1 1 d . . . H8A H 0.2594(8) 0.1838(13) 0.1057(6) 0.016(3) Uiso 1 1 d . . . H8B H 0.2932(8) 0.3075(13) 0.0593(7) 0.018(3) Uiso 1 1 d . . . C9 C 0.20233(7) 0.36062(11) 0.13567(6) 0.0158(2) Uani 1 1 d . . . H9A H 0.1526(9) 0.3517(13) 0.1034(7) 0.021(3) Uiso 1 1 d . . . H9B H 0.2186(8) 0.4574(14) 0.1375(7) 0.020(3) Uiso 1 1 d . . . C10 C 0.17777(6) 0.31590(10) 0.21009(5) 0.0126(2) Uani 1 1 d . . . C11 C 0.10328(6) 0.39586(10) 0.23870(5) 0.0129(2) Uani 1 1 d . . . C12 C 0.02878(6) 0.45090(10) 0.21089(5) 0.0138(2) Uani 1 1 d . . . C13 C -0.01446(6) 0.43624(11) 0.14238(5) 0.0143(2) Uani 1 1 d . . . C14 C -0.01383(7) 0.31629(11) 0.10555(6) 0.0162(2) Uani 1 1 d . . . H14 H 0.0151(8) 0.2400(14) 0.1248(7) 0.018(3) Uiso 1 1 d . . . C15 C -0.05779(7) 0.30479(12) 0.04230(6) 0.0187(2) Uani 1 1 d . . . H15 H -0.0576(9) 0.2201(14) 0.0180(7) 0.024(3) Uiso 1 1 d . . . C16 C -0.10294(7) 0.41216(12) 0.01522(6) 0.0194(3) Uani 1 1 d . . . H16 H -0.1333(9) 0.4045(13) -0.0299(7) 0.022(3) Uiso 1 1 d . . . C17 C -0.10510(7) 0.53098(12) 0.05210(6) 0.0190(2) Uani 1 1 d . . . H17 H -0.1369(9) 0.6082(14) 0.0335(7) 0.023(3) Uiso 1 1 d . . . C18 C -0.06105(7) 0.54290(11) 0.11523(6) 0.0168(2) Uani 1 1 d . . . H18 H -0.0610(8) 0.6274(14) 0.1411(7) 0.019(3) 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 0.0140(4) 0.0107(4) 0.0329(5) -0.0025(3) 0.0058(3) -0.0019(3) N1 0.0136(4) 0.0122(5) 0.0154(4) -0.0005(3) 0.0003(3) 0.0009(3) N2 0.0154(4) 0.0146(5) 0.0185(5) -0.0007(3) 0.0016(4) 0.0022(3) N3 0.0139(4) 0.0148(5) 0.0178(5) 0.0002(3) 0.0013(3) 0.0014(3) C1 0.0294(7) 0.0304(7) 0.0193(6) -0.0025(5) -0.0009(5) 0.0018(5) C2 0.0206(5) 0.0160(6) 0.0190(6) 0.0004(4) 0.0000(4) 0.0019(4) C3 0.0160(5) 0.0152(6) 0.0161(5) -0.0006(4) -0.0032(4) -0.0007(4) C4 0.0156(5) 0.0175(6) 0.0180(5) 0.0003(4) -0.0029(4) 0.0021(4) C5 0.0130(5) 0.0130(6) 0.0180(5) -0.0002(4) -0.0014(4) -0.0006(4) C6 0.0122(5) 0.0199(6) 0.0226(6) -0.0016(4) -0.0026(4) 0.0021(4) C7 0.0124(5) 0.0212(6) 0.0248(6) -0.0023(5) 0.0029(4) 0.0001(4) C8 0.0156(5) 0.0165(6) 0.0179(5) -0.0003(4) 0.0033(4) 0.0013(4) C9 0.0152(5) 0.0155(6) 0.0167(5) 0.0011(4) 0.0010(4) 0.0023(4) C10 0.0116(5) 0.0095(5) 0.0168(5) -0.0002(4) 0.0005(4) 0.0001(4) C11 0.0137(5) 0.0101(5) 0.0149(5) 0.0004(4) 0.0009(4) -0.0016(4) C12 0.0125(5) 0.0115(5) 0.0174(5) 0.0009(4) 0.0023(4) -0.0004(4) C13 0.0094(5) 0.0163(6) 0.0172(5) 0.0016(4) 0.0015(4) -0.0012(4) C14 0.0135(5) 0.0154(6) 0.0197(5) 0.0020(4) 0.0019(4) 0.0003(4) C15 0.0169(5) 0.0182(6) 0.0210(6) -0.0026(4) 0.0019(4) -0.0030(4) C16 0.0156(5) 0.0238(6) 0.0188(6) 0.0003(4) -0.0027(4) -0.0032(4) C17 0.0153(5) 0.0189(6) 0.0229(6) 0.0030(4) -0.0028(4) 0.0009(4) C18 0.0140(5) 0.0157(6) 0.0208(5) -0.0003(4) -0.0005(4) 0.0005(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 C10 1.4319(13) . ? O1 H1O 0.889(17) . ? N1 N2 1.3388(12) . ? N1 C11 1.3643(14) . ? N1 C3 1.4807(13) . ? N2 N3 1.3154(13) . ? N3 C12 1.3682(14) . ? C1 C2 1.3173(17) . ? C1 H1A 0.984(17) . ? C1 H1B 0.989(16) . ? C2 C3 1.5058(15) . ? C2 H2 0.982(15) . ? C3 C4 1.5328(15) . ? C3 H3 0.978(14) . ? C4 C5 1.5291(14) . ? C4 H4A 1.009(14) . ? C4 H4B 0.990(15) . ? C5 C6 1.5287(15) . ? C5 C10 1.5499(14) . ? C5 H5 0.994(13) . ? C6 C7 1.5329(16) . ? C6 H6A 1.009(14) . ? C6 H6B 0.987(14) . ? C7 C8 1.5283(15) . ? C7 H7A 0.990(15) . ? C7 H7B 1.015(14) . ? C8 C9 1.5316(14) . ? C8 H8A 0.997(13) . ? C8 H8B 1.014(13) . ? C9 C10 1.5368(14) . ? C9 H9A 0.992(14) . ? C9 H9B 1.008(14) . ? C10 C11 1.5127(14) . ? C11 C12 1.3895(15) . ? C12 C13 1.4764(14) . ? C13 C18 1.3957(15) . ? C13 C14 1.3980(15) . ? C14 C15 1.3908(16) . ? C14 H14 0.964(14) . ? C15 C16 1.3892(16) . ? C15 H15 0.971(14) . ? C16 C17 1.3889(17) . ? C16 H16 0.984(14) . ? C17 C18 1.3899(16) . ? C17 H17 0.988(14) . ? C18 H18 0.984(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 C10 O1 H1O 115.1(10) . . ? N2 N1 C11 112.00(8) . . ? N2 N1 C3 119.27(8) . . ? C11 N1 C3 128.66(9) . . ? N3 N2 N1 106.85(8) . . ? N2 N3 C12 109.61(8) . . ? C2 C1 H1A 120.2(9) . . ? C2 C1 H1B 122.1(9) . . ? H1A C1 H1B 117.7(13) . . ? C1 C2 C3 123.94(11) . . ? C1 C2 H2 120.7(8) . . ? C3 C2 H2 115.4(8) . . ? N1 C3 C2 109.45(9) . . ? N1 C3 C4 107.82(8) . . ? C2 C3 C4 114.32(9) . . ? N1 C3 H3 106.1(7) . . ? C2 C3 H3 109.5(7) . . ? C4 C3 H3 109.3(8) . . ? C5 C4 C3 110.36(9) . . ? C5 C4 H4A 110.0(7) . . ? C3 C4 H4A 110.7(7) . . ? C5 C4 H4B 111.5(8) . . ? C3 C4 H4B 107.7(8) . . ? H4A C4 H4B 106.5(11) . . ? C6 C5 C4 113.80(9) . . ? C6 C5 C10 109.86(8) . . ? C4 C5 C10 109.98(8) . . ? C6 C5 H5 108.2(7) . . ? C4 C5 H5 107.8(7) . . ? C10 C5 H5 107.0(7) . . ? C5 C6 C7 110.80(9) . . ? C5 C6 H6A 108.6(7) . . ? C7 C6 H6A 110.1(7) . . ? C5 C6 H6B 108.5(8) . . ? C7 C6 H6B 110.0(8) . . ? H6A C6 H6B 108.8(11) . . ? C8 C7 C6 111.18(9) . . ? C8 C7 H7A 109.1(8) . . ? C6 C7 H7A 109.1(8) . . ? C8 C7 H7B 109.8(8) . . ? C6 C7 H7B 110.0(8) . . ? H7A C7 H7B 107.6(11) . . ? C7 C8 C9 111.52(9) . . ? C7 C8 H8A 109.7(7) . . ? C9 C8 H8A 108.2(7) . . ? C7 C8 H8B 111.0(7) . . ? C9 C8 H8B 109.3(7) . . ? H8A C8 H8B 107.0(10) . . ? C8 C9 C10 110.03(9) . . ? C8 C9 H9A 110.1(8) . . ? C10 C9 H9A 110.6(8) . . ? C8 C9 H9B 110.1(8) . . ? C10 C9 H9B 108.3(7) . . ? H9A C9 H9B 107.7(11) . . ? O1 C10 C11 112.32(8) . . ? O1 C10 C9 107.74(9) . . ? C11 C10 C9 111.53(9) . . ? O1 C10 C5 108.71(8) . . ? C11 C10 C5 108.37(8) . . ? C9 C10 C5 108.05(8) . . ? N1 C11 C12 103.50(9) . . ? N1 C11 C10 120.67(9) . . ? C12 C11 C10 135.51(9) . . ? N3 C12 C11 108.01(9) . . ? N3 C12 C13 119.33(9) . . ? C11 C12 C13 132.63(10) . . ? C18 C13 C14 118.91(10) . . ? C18 C13 C12 119.16(10) . . ? C14 C13 C12 121.85(10) . . ? C15 C14 C13 120.26(10) . . ? C15 C14 H14 119.6(8) . . ? C13 C14 H14 120.1(8) . . ? C16 C15 C14 120.37(10) . . ? C16 C15 H15 120.6(8) . . ? C14 C15 H15 119.1(8) . . ? C17 C16 C15 119.71(10) . . ? C17 C16 H16 119.9(8) . . ? C15 C16 H16 120.4(8) . . ? C16 C17 C18 120.05(10) . . ? C16 C17 H17 120.6(8) . . ? C18 C17 H17 119.3(8) . . ? C17 C18 C13 120.68(10) . . ? C17 C18 H18 120.6(8) . . ? C13 C18 H18 118.7(8) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C11 N1 N2 N3 0.66(11) . . . . ? C3 N1 N2 N3 177.82(9) . . . . ? N1 N2 N3 C12 0.45(11) . . . . ? N2 N1 C3 C2 48.23(12) . . . . ? C11 N1 C3 C2 -135.13(11) . . . . ? N2 N1 C3 C4 173.13(9) . . . . ? C11 N1 C3 C4 -10.23(14) . . . . ? C1 C2 C3 N1 -138.43(12) . . . . ? C1 C2 C3 C4 100.53(14) . . . . ? N1 C3 C4 C5 44.80(11) . . . . ? C2 C3 C4 C5 166.74(9) . . . . ? C3 C4 C5 C6 167.38(9) . . . . ? C3 C4 C5 C10 -68.88(11) . . . . ? C4 C5 C6 C7 -177.38(9) . . . . ? C10 C5 C6 C7 58.81(12) . . . . ? C5 C6 C7 C8 -54.66(12) . . . . ? C6 C7 C8 C9 54.14(13) . . . . ? C7 C8 C9 C10 -57.78(12) . . . . ? C8 C9 C10 O1 -56.65(11) . . . . ? C8 C9 C10 C11 179.65(9) . . . . ? C8 C9 C10 C5 60.65(11) . . . . ? C6 C5 C10 O1 55.17(11) . . . . ? C4 C5 C10 O1 -70.84(11) . . . . ? C6 C5 C10 C11 177.51(8) . . . . ? C4 C5 C10 C11 51.51(11) . . . . ? C6 C5 C10 C9 -61.50(11) . . . . ? C4 C5 C10 C9 172.50(9) . . . . ? N2 N1 C11 C12 -1.43(11) . . . . ? C3 N1 C11 C12 -178.27(10) . . . . ? N2 N1 C11 C10 173.07(9) . . . . ? C3 N1 C11 C10 -3.76(16) . . . . ? O1 C10 C11 N1 103.10(11) . . . . ? C9 C10 C11 N1 -135.83(10) . . . . ? C5 C10 C11 N1 -17.02(13) . . . . ? O1 C10 C11 C12 -84.54(15) . . . . ? C9 C10 C11 C12 36.52(16) . . . . ? C5 C10 C11 C12 155.34(12) . . . . ? N2 N3 C12 C11 -1.35(12) . . . . ? N2 N3 C12 C13 176.78(9) . . . . ? N1 C11 C12 N3 1.64(11) . . . . ? C10 C11 C12 N3 -171.61(11) . . . . ? N1 C11 C12 C13 -176.15(11) . . . . ? C10 C11 C12 C13 10.6(2) . . . . ? N3 C12 C13 C18 33.25(14) . . . . ? C11 C12 C13 C18 -149.16(12) . . . . ? N3 C12 C13 C14 -143.36(10) . . . . ? C11 C12 C13 C14 34.23(17) . . . . ? C18 C13 C14 C15 1.12(15) . . . . ? C12 C13 C14 C15 177.74(9) . . . . ? C13 C14 C15 C16 -0.19(16) . . . . ? C14 C15 C16 C17 -0.91(16) . . . . ? C15 C16 C17 C18 1.07(16) . . . . ? C16 C17 C18 C13 -0.13(16) . . . . ? C14 C13 C18 C17 -0.97(16) . . . . ? C12 C13 C18 C17 -177.68(10) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1 H1O N3 0.889(17) 2.019(17) 2.8464(12) 154.3(14) 3_545 _diffrn_measured_fraction_theta_max 0.964 _diffrn_reflns_theta_full 66.00 _diffrn_measured_fraction_theta_full 0.980 _refine_diff_density_max 0.278 _refine_diff_density_min -0.192 _refine_diff_density_rms 0.036 #===END data_28a _audit_creation_method SHELXTL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H21 N3 O' _chemical_formula_weight 295.38 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 6.7407(4) _cell_length_b 16.6911(10) _cell_length_c 13.8906(8) _cell_angle_alpha 90.00 _cell_angle_beta 98.6652(16) _cell_angle_gamma 90.00 _cell_volume 1544.99(16) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 9944 _cell_measurement_theta_min 4.17 _cell_measurement_theta_max 69.65 _exptl_crystal_description 'Rectangular parallelepiped' _exptl_crystal_colour colourless _exptl_crystal_size_max 0.36 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.270 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 632 _exptl_absorpt_coefficient_mu 0.636 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.894 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'Bruker MicroStar microfocus rotating anode' _diffrn_radiation_monochromator 'Helios multilayer optics' _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0.00 _diffrn_reflns_number 13824 _diffrn_reflns_av_R_equivalents 0.0210 _diffrn_reflns_av_sigmaI/netI 0.0188 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 4.17 _diffrn_reflns_theta_max 69.64 _reflns_number_total 2766 _reflns_number_gt 2757 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0303P)^2^+0.7933P] 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 SHELXL _refine_ls_extinction_coef 0.0047(5) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 2766 _refine_ls_number_parameters 284 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0341 _refine_ls_R_factor_gt 0.0340 _refine_ls_wR_factor_ref 0.0802 _refine_ls_wR_factor_gt 0.0801 _refine_ls_goodness_of_fit_ref 1.059 _refine_ls_restrained_S_all 1.059 _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 0.11154(11) 0.21263(5) -0.04579(6) 0.0152(2) Uani 1 1 d . . . H1O H 0.059(3) 0.2207(10) -0.1078(14) 0.035(4) Uiso 1 1 d . . . N1 N 0.52645(13) 0.20346(5) 0.10224(7) 0.0130(2) Uani 1 1 d . . . N2 N 0.59030(14) 0.20343(6) 0.19836(7) 0.0160(2) Uani 1 1 d . . . N3 N 0.47666(14) 0.25482(6) 0.23761(7) 0.0144(2) Uani 1 1 d . . . C1 C 0.8639(2) 0.04331(8) 0.08099(10) 0.0270(3) Uani 1 1 d . . . H1A H 0.981(3) 0.0756(11) 0.0720(13) 0.041(5) Uiso 1 1 d . . . H1B H 0.886(3) -0.0142(11) 0.1006(12) 0.038(4) Uiso 1 1 d . . . C2 C 0.68292(19) 0.07516(7) 0.07042(8) 0.0192(3) Uani 1 1 d . . . H2 H 0.560(2) 0.0438(9) 0.0803(10) 0.021(3) Uiso 1 1 d . . . C3 C 0.64154(17) 0.15954(7) 0.03575(8) 0.0156(3) Uani 1 1 d . . . H3 H 0.776(2) 0.1878(8) 0.0373(10) 0.016(3) Uiso 1 1 d . . . C4 C 0.52160(17) 0.16269(7) -0.06644(8) 0.0160(3) Uani 1 1 d . . . H4A H 0.613(2) 0.1457(8) -0.1128(11) 0.020(3) Uiso 1 1 d . . . H4B H 0.414(2) 0.1254(8) -0.0702(10) 0.017(3) Uiso 1 1 d . . . C5 C 0.43754(16) 0.24631(6) -0.09299(8) 0.0133(2) Uani 1 1 d . . . H5 H 0.3652(19) 0.2449(8) -0.1604(10) 0.012(3) Uiso 1 1 d . . . C6 C 0.60366(17) 0.31002(7) -0.08786(9) 0.0171(3) Uani 1 1 d . . . H6A H 0.694(2) 0.2946(8) -0.1341(11) 0.023(4) Uiso 1 1 d . . . H6B H 0.687(2) 0.3098(8) -0.0219(11) 0.020(3) Uiso 1 1 d . . . C7 C 0.51922(18) 0.39418(7) -0.10918(9) 0.0191(3) Uani 1 1 d . . . H7A H 0.449(2) 0.3971(8) -0.1791(11) 0.021(3) Uiso 1 1 d . . . H7B H 0.630(2) 0.4338(9) -0.1024(10) 0.023(4) Uiso 1 1 d . . . C8 C 0.37140(17) 0.41484(7) -0.03962(9) 0.0166(3) Uani 1 1 d . . . H8A H 0.444(2) 0.4157(8) 0.0295(11) 0.020(3) Uiso 1 1 d . . . H8B H 0.315(2) 0.4688(9) -0.0530(11) 0.022(3) Uiso 1 1 d . . . C9 C 0.20202(16) 0.35338(7) -0.04825(8) 0.0135(2) Uani 1 1 d . . . H9A H 0.102(2) 0.3679(8) -0.0050(10) 0.017(3) Uiso 1 1 d . . . H9B H 0.129(2) 0.3548(8) -0.1175(11) 0.015(3) Uiso 1 1 d . . . C10 C 0.27836(16) 0.26759(6) -0.02748(8) 0.0121(2) Uani 1 1 d . . . C11 C 0.37028(15) 0.25513(6) 0.07735(8) 0.0118(2) Uani 1 1 d . . . C12 C 0.34039(16) 0.28771(6) 0.16575(8) 0.0123(2) Uani 1 1 d . . . C13 C 0.19795(16) 0.34999(6) 0.18800(8) 0.0127(2) Uani 1 1 d . . . C14 C -0.00881(17) 0.33631(7) 0.16989(8) 0.0170(3) Uani 1 1 d . . . H14 H -0.058(2) 0.2841(9) 0.1441(10) 0.021(3) Uiso 1 1 d . . . C15 C -0.14138(18) 0.39624(8) 0.18753(9) 0.0214(3) Uani 1 1 d . . . H15 H -0.288(2) 0.3841(9) 0.1746(11) 0.028(4) Uiso 1 1 d . . . C16 C -0.07029(19) 0.47003(8) 0.22329(9) 0.0218(3) Uani 1 1 d . . . H16 H -0.162(2) 0.5118(10) 0.2354(11) 0.030(4) Uiso 1 1 d . . . C17 C 0.1351(2) 0.48358(7) 0.24313(9) 0.0215(3) Uani 1 1 d . . . H17 H 0.188(2) 0.5350(9) 0.2702(11) 0.029(4) Uiso 1 1 d . . . C18 C 0.26851(17) 0.42368(7) 0.22585(8) 0.0173(3) Uani 1 1 d . . . H18 H 0.413(2) 0.4334(9) 0.2390(10) 0.023(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 0.0148(4) 0.0179(4) 0.0117(4) -0.0001(3) -0.0018(3) -0.0044(3) N1 0.0150(4) 0.0154(5) 0.0080(5) 0.0002(3) -0.0003(4) 0.0022(4) N2 0.0181(5) 0.0205(5) 0.0087(5) -0.0009(4) -0.0002(4) 0.0038(4) N3 0.0147(4) 0.0176(5) 0.0104(5) -0.0006(3) 0.0011(4) 0.0027(4) C1 0.0325(7) 0.0263(7) 0.0227(7) 0.0041(5) 0.0052(6) 0.0131(6) C2 0.0261(6) 0.0188(6) 0.0128(6) -0.0002(4) 0.0035(5) 0.0031(5) C3 0.0168(5) 0.0178(6) 0.0126(6) -0.0012(4) 0.0034(4) 0.0032(4) C4 0.0194(6) 0.0171(6) 0.0113(6) -0.0020(4) 0.0020(4) 0.0026(5) C5 0.0150(5) 0.0161(6) 0.0084(6) -0.0005(4) 0.0005(4) 0.0018(4) C6 0.0146(5) 0.0223(6) 0.0148(6) 0.0015(4) 0.0035(5) -0.0006(4) C7 0.0205(6) 0.0198(6) 0.0173(6) 0.0035(4) 0.0036(5) -0.0040(5) C8 0.0210(6) 0.0136(6) 0.0142(6) 0.0006(4) -0.0003(5) 0.0001(4) C9 0.0144(5) 0.0154(6) 0.0102(6) 0.0007(4) 0.0003(4) 0.0018(4) C10 0.0120(5) 0.0139(5) 0.0099(6) -0.0006(4) 0.0004(4) -0.0017(4) C11 0.0113(5) 0.0120(5) 0.0118(6) 0.0004(4) 0.0009(4) -0.0005(4) C12 0.0117(5) 0.0148(5) 0.0105(6) 0.0003(4) 0.0013(4) -0.0021(4) C13 0.0152(5) 0.0168(5) 0.0062(5) 0.0017(4) 0.0024(4) 0.0015(4) C14 0.0158(5) 0.0232(6) 0.0115(6) -0.0011(4) 0.0009(4) 0.0000(4) C15 0.0154(6) 0.0355(7) 0.0132(6) 0.0009(5) 0.0012(4) 0.0062(5) C16 0.0270(6) 0.0261(6) 0.0135(6) 0.0043(5) 0.0068(5) 0.0133(5) C17 0.0314(7) 0.0167(6) 0.0181(6) -0.0003(4) 0.0092(5) 0.0016(5) C18 0.0175(6) 0.0192(6) 0.0160(6) -0.0011(4) 0.0056(4) -0.0020(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 C10 1.4438(13) . ? O1 H1O 0.892(19) . ? N1 N2 1.3397(13) . ? N1 C11 1.3645(14) . ? N1 C3 1.4860(14) . ? N2 N3 1.3212(13) . ? N3 C12 1.3657(14) . ? C1 C2 1.3183(18) . ? C1 H1A 0.978(18) . ? C1 H1B 1.002(18) . ? C2 C3 1.5009(16) . ? C2 H2 1.007(15) . ? C3 C4 1.5250(16) . ? C3 H3 1.018(14) . ? C4 C5 1.5303(15) . ? C4 H4A 0.998(15) . ? C4 H4B 0.953(14) . ? C5 C6 1.5381(15) . ? C5 C10 1.5491(14) . ? C5 H5 0.989(14) . ? C6 C7 1.5277(16) . ? C6 H6A 0.984(15) . ? C6 H6B 0.999(15) . ? C7 C8 1.5283(16) . ? C7 H7A 1.015(15) . ? C7 H7B 0.994(15) . ? C8 C9 1.5261(15) . ? C8 H8A 1.010(15) . ? C8 H8B 0.985(15) . ? C9 C10 1.5343(15) . ? C9 H9A 0.996(14) . ? C9 H9B 1.012(14) . ? C10 C11 1.5085(15) . ? C11 C12 1.3851(15) . ? C12 C13 1.4790(15) . ? C13 C18 1.3929(16) . ? C13 C14 1.3972(16) . ? C14 C15 1.3876(17) . ? C14 H14 0.980(15) . ? C15 C16 1.3861(19) . ? C15 H15 0.996(16) . ? C16 C17 1.3886(19) . ? C16 H16 0.962(16) . ? C17 C18 1.3899(17) . ? C17 H17 0.982(16) . ? C18 H18 0.980(15) . ? 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 C10 O1 H1O 105.2(11) . . ? N2 N1 C11 111.87(9) . . ? N2 N1 C3 119.99(9) . . ? C11 N1 C3 127.55(10) . . ? N3 N2 N1 106.97(9) . . ? N2 N3 C12 109.11(9) . . ? C2 C1 H1A 120.8(10) . . ? C2 C1 H1B 120.9(10) . . ? H1A C1 H1B 118.2(14) . . ? C1 C2 C3 122.57(12) . . ? C1 C2 H2 122.8(8) . . ? C3 C2 H2 114.5(8) . . ? N1 C3 C2 110.65(9) . . ? N1 C3 C4 107.95(9) . . ? C2 C3 C4 112.20(9) . . ? N1 C3 H3 107.7(8) . . ? C2 C3 H3 107.8(8) . . ? C4 C3 H3 110.4(8) . . ? C3 C4 C5 112.39(9) . . ? C3 C4 H4A 107.3(8) . . ? C5 C4 H4A 110.2(8) . . ? C3 C4 H4B 108.8(8) . . ? C5 C4 H4B 109.3(8) . . ? H4A C4 H4B 108.7(11) . . ? C4 C5 C6 112.26(9) . . ? C4 C5 C10 109.37(9) . . ? C6 C5 C10 112.22(9) . . ? C4 C5 H5 108.6(7) . . ? C6 C5 H5 108.2(7) . . ? C10 C5 H5 106.0(7) . . ? C7 C6 C5 112.29(9) . . ? C7 C6 H6A 111.3(8) . . ? C5 C6 H6A 107.9(8) . . ? C7 C6 H6B 108.8(8) . . ? C5 C6 H6B 110.0(8) . . ? H6A C6 H6B 106.3(11) . . ? C6 C7 C8 110.14(9) . . ? C6 C7 H7A 109.7(8) . . ? C8 C7 H7A 109.8(8) . . ? C6 C7 H7B 109.9(8) . . ? C8 C7 H7B 110.2(8) . . ? H7A C7 H7B 107.1(11) . . ? C9 C8 C7 110.48(9) . . ? C9 C8 H8A 109.5(8) . . ? C7 C8 H8A 109.6(8) . . ? C9 C8 H8B 109.6(8) . . ? C7 C8 H8B 111.0(8) . . ? H8A C8 H8B 106.5(11) . . ? C8 C9 C10 112.76(9) . . ? C8 C9 H9A 110.7(8) . . ? C10 C9 H9A 110.6(8) . . ? C8 C9 H9B 108.1(7) . . ? C10 C9 H9B 107.6(8) . . ? H9A C9 H9B 106.9(11) . . ? O1 C10 C11 106.16(8) . . ? O1 C10 C9 109.25(8) . . ? C11 C10 C9 112.80(9) . . ? O1 C10 C5 109.93(9) . . ? C11 C10 C5 108.38(9) . . ? C9 C10 C5 110.23(9) . . ? N1 C11 C12 103.49(9) . . ? N1 C11 C10 121.37(10) . . ? C12 C11 C10 135.09(10) . . ? N3 C12 C11 108.57(9) . . ? N3 C12 C13 121.07(9) . . ? C11 C12 C13 130.31(10) . . ? C18 C13 C14 119.13(10) . . ? C18 C13 C12 120.27(10) . . ? C14 C13 C12 120.59(10) . . ? C15 C14 C13 120.13(11) . . ? C15 C14 H14 121.1(8) . . ? C13 C14 H14 118.8(8) . . ? C16 C15 C14 120.45(11) . . ? C16 C15 H15 121.6(9) . . ? C14 C15 H15 117.9(9) . . ? C15 C16 C17 119.76(11) . . ? C15 C16 H16 120.8(9) . . ? C17 C16 H16 119.5(9) . . ? C16 C17 C18 120.02(12) . . ? C16 C17 H17 120.8(9) . . ? C18 C17 H17 119.2(9) . . ? C17 C18 C13 120.49(11) . . ? C17 C18 H18 120.2(9) . . ? C13 C18 H18 119.3(8) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C11 N1 N2 N3 0.16(12) . . . . ? C3 N1 N2 N3 171.98(9) . . . . ? N1 N2 N3 C12 -0.16(12) . . . . ? N2 N1 C3 C2 50.76(13) . . . . ? C11 N1 C3 C2 -138.83(11) . . . . ? N2 N1 C3 C4 173.90(9) . . . . ? C11 N1 C3 C4 -15.69(15) . . . . ? C1 C2 C3 N1 -129.42(12) . . . . ? C1 C2 C3 C4 109.94(14) . . . . ? N1 C3 C4 C5 44.57(12) . . . . ? C2 C3 C4 C5 166.76(9) . . . . ? C3 C4 C5 C6 58.76(12) . . . . ? C3 C4 C5 C10 -66.48(12) . . . . ? C4 C5 C6 C7 -177.02(9) . . . . ? C10 C5 C6 C7 -53.36(13) . . . . ? C5 C6 C7 C8 56.08(13) . . . . ? C6 C7 C8 C9 -57.63(13) . . . . ? C7 C8 C9 C10 57.88(13) . . . . ? C8 C9 C10 O1 -174.80(9) . . . . ? C8 C9 C10 C11 67.40(12) . . . . ? C8 C9 C10 C5 -53.90(12) . . . . ? C4 C5 C10 O1 -63.21(11) . . . . ? C6 C5 C10 O1 171.53(9) . . . . ? C4 C5 C10 C11 52.41(11) . . . . ? C6 C5 C10 C11 -72.85(11) . . . . ? C4 C5 C10 C9 176.30(9) . . . . ? C6 C5 C10 C9 51.04(12) . . . . ? N2 N1 C11 C12 -0.09(12) . . . . ? C3 N1 C11 C12 -171.15(10) . . . . ? N2 N1 C11 C10 177.73(9) . . . . ? C3 N1 C11 C10 6.67(16) . . . . ? O1 C10 C11 N1 93.42(11) . . . . ? C9 C10 C11 N1 -146.98(10) . . . . ? C5 C10 C11 N1 -24.63(13) . . . . ? O1 C10 C11 C12 -89.58(14) . . . . ? C9 C10 C11 C12 30.02(17) . . . . ? C5 C10 C11 C12 152.37(12) . . . . ? N2 N3 C12 C11 0.10(12) . . . . ? N2 N3 C12 C13 -177.57(9) . . . . ? N1 C11 C12 N3 0.00(11) . . . . ? C10 C11 C12 N3 -177.37(11) . . . . ? N1 C11 C12 C13 177.38(10) . . . . ? C10 C11 C12 C13 0.0(2) . . . . ? N3 C12 C13 C18 63.08(14) . . . . ? C11 C12 C13 C18 -114.03(13) . . . . ? N3 C12 C13 C14 -117.99(12) . . . . ? C11 C12 C13 C14 64.90(16) . . . . ? C18 C13 C14 C15 1.41(17) . . . . ? C12 C13 C14 C15 -177.53(10) . . . . ? C13 C14 C15 C16 -0.08(18) . . . . ? C14 C15 C16 C17 -1.09(18) . . . . ? C15 C16 C17 C18 0.90(18) . . . . ? C16 C17 C18 C13 0.45(17) . . . . ? C14 C13 C18 C17 -1.59(17) . . . . ? C12 C13 C18 C17 177.34(10) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1 H1O N3 0.892(19) 2.174(19) 3.0578(13) 171.0(15) 4_565 _diffrn_measured_fraction_theta_max 0.951 _diffrn_reflns_theta_full 66.00 _diffrn_measured_fraction_theta_full 0.969 _refine_diff_density_max 0.256 _refine_diff_density_min -0.188 _refine_diff_density_rms 0.038 #===END data_29a _audit_creation_method SHELXTL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H31 N3 O2' _chemical_formula_weight 369.50 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 9.2253(3) _cell_length_b 10.5676(3) _cell_length_c 21.0165(6) _cell_angle_alpha 90.00 _cell_angle_beta 97.5590(10) _cell_angle_gamma 90.00 _cell_volume 2031.08(11) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 9866 _cell_measurement_theta_min 4.69 _cell_measurement_theta_max 69.80 _exptl_crystal_description 'Rectangular parallelepiped' _exptl_crystal_colour colourless _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.208 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 800 _exptl_absorpt_coefficient_mu 0.615 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.928 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'Bruker MicroStar microfocus rotating anode' _diffrn_radiation_monochromator 'Helios multilayer optics' _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0.00 _diffrn_reflns_number 18553 _diffrn_reflns_av_R_equivalents 0.0140 _diffrn_reflns_av_sigmaI/netI 0.0102 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 4.24 _diffrn_reflns_theta_max 69.80 _reflns_number_total 3588 _reflns_number_gt 3490 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0371P)^2^+0.9116P] 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 SHELXL _refine_ls_extinction_coef 0.00104(16) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 3588 _refine_ls_number_parameters 369 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0336 _refine_ls_R_factor_gt 0.0330 _refine_ls_wR_factor_ref 0.0812 _refine_ls_wR_factor_gt 0.0809 _refine_ls_goodness_of_fit_ref 1.024 _refine_ls_restrained_S_all 1.024 _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 0.29920(8) 0.40042(7) 0.16650(4) 0.01913(19) Uani 1 1 d . . . H1O H 0.2434(19) 0.3569(16) 0.1363(8) 0.045(5) Uiso 1 1 d . . . N1 N -0.03471(10) 0.52313(9) 0.12549(4) 0.0176(2) Uani 1 1 d . . . N2 N -0.10659(10) 0.57537(9) 0.07243(4) 0.0199(2) Uani 1 1 d . . . N3 N -0.00837(10) 0.63568(9) 0.04383(4) 0.0182(2) Uani 1 1 d . . . C1 C -0.36409(13) 0.36301(13) 0.14201(6) 0.0266(3) Uani 1 1 d . . . H1A H -0.3974(17) 0.4177(15) 0.1734(8) 0.036(4) Uiso 1 1 d . . . H1B H -0.4342(16) 0.3060(14) 0.1183(7) 0.032(4) Uiso 1 1 d . . . C2 C -0.22759(13) 0.36607(11) 0.13063(5) 0.0221(3) Uani 1 1 d . . . H2 H -0.1910(16) 0.3109(14) 0.0977(7) 0.030(4) Uiso 1 1 d . . . C3 C -0.11384(12) 0.44658(11) 0.16870(5) 0.0194(2) Uani 1 1 d . . . H3 H -0.1638(14) 0.5060(13) 0.1960(6) 0.021(3) Uiso 1 1 d . . . C4 C -0.00006(13) 0.36942(11) 0.21197(5) 0.0200(2) Uani 1 1 d . . . H4A H 0.0353(13) 0.3039(12) 0.1874(6) 0.012(3) Uiso 1 1 d . . . H4B H -0.0514(15) 0.3293(13) 0.2450(7) 0.025(3) Uiso 1 1 d . . . C5 C 0.12376(12) 0.45531(10) 0.24163(5) 0.0176(2) Uani 1 1 d . . . H5 H 0.0768(14) 0.5343(13) 0.2558(6) 0.020(3) Uiso 1 1 d . . . C6 C 0.21807(13) 0.40264(11) 0.30272(5) 0.0201(2) Uani 1 1 d . . . C7 C 0.33256(14) 0.50400(12) 0.32667(5) 0.0233(3) Uani 1 1 d . . . H7A H 0.3984(15) 0.4689(13) 0.3639(7) 0.025(3) Uiso 1 1 d . . . H7B H 0.2807(15) 0.5780(13) 0.3428(6) 0.023(3) Uiso 1 1 d . . . C8 C 0.42070(13) 0.55238(12) 0.27516(5) 0.0236(3) Uani 1 1 d . . . H8A H 0.4824(15) 0.4845(13) 0.2620(6) 0.022(3) Uiso 1 1 d . . . H8B H 0.4866(16) 0.6220(14) 0.2931(7) 0.031(4) Uiso 1 1 d . . . C9 C 0.32173(13) 0.60285(11) 0.21678(5) 0.0199(2) Uani 1 1 d . . . H9A H 0.2646(15) 0.6766(13) 0.2301(6) 0.023(3) Uiso 1 1 d . . . H9B H 0.3803(14) 0.6323(12) 0.1848(6) 0.020(3) Uiso 1 1 d . . . C10 C 0.21428(12) 0.50071(10) 0.18865(5) 0.0164(2) Uani 1 1 d . . . C11 C 0.11035(11) 0.55035(10) 0.13233(5) 0.0164(2) Uani 1 1 d . . . C12 C 0.12678(12) 0.62196(10) 0.07857(5) 0.0163(2) Uani 1 1 d . . . C13 C 0.25688(12) 0.67755(10) 0.05528(5) 0.0175(2) Uani 1 1 d . . . C14 C 0.38844(12) 0.61073(11) 0.05912(5) 0.0202(2) Uani 1 1 d . . . H14 H 0.3946(14) 0.5267(14) 0.0768(6) 0.023(3) Uiso 1 1 d . . . C15 C 0.50973(13) 0.66427(12) 0.03672(5) 0.0239(3) Uani 1 1 d . . . H15 H 0.6004(16) 0.6167(14) 0.0399(7) 0.031(4) Uiso 1 1 d . . . C16 C 0.50000(14) 0.78431(12) 0.00968(6) 0.0267(3) Uani 1 1 d . . . H16 H 0.5847(16) 0.8209(14) -0.0067(7) 0.031(4) Uiso 1 1 d . . . C17 C 0.36926(14) 0.85064(12) 0.00472(6) 0.0261(3) Uani 1 1 d . . . H17 H 0.3601(16) 0.9342(15) -0.0150(7) 0.035(4) Uiso 1 1 d . . . C18 C 0.24832(13) 0.79774(11) 0.02756(5) 0.0210(2) Uani 1 1 d . . . H18 H 0.1588(15) 0.8436(13) 0.0242(6) 0.023(3) Uiso 1 1 d . . . C19 C 0.29230(15) 0.27580(12) 0.29216(6) 0.0253(3) Uani 1 1 d . . . H19A H 0.2176(17) 0.2126(15) 0.2729(7) 0.035(4) Uiso 1 1 d . . . H19B H 0.3686(17) 0.2837(14) 0.2628(7) 0.033(4) Uiso 1 1 d . . . H19C H 0.3377(16) 0.2425(14) 0.3333(7) 0.034(4) Uiso 1 1 d . . . C20 C 0.12016(15) 0.38317(13) 0.35563(6) 0.0286(3) Uani 1 1 d . . . H20A H 0.1819(17) 0.3621(15) 0.3975(8) 0.037(4) Uiso 1 1 d . . . H20B H 0.0488(16) 0.3124(15) 0.3455(7) 0.033(4) Uiso 1 1 d . . . H20C H 0.0659(16) 0.4619(14) 0.3624(7) 0.031(4) Uiso 1 1 d . . . O1S O 0.13779(12) 0.26432(9) 0.07107(4) 0.0411(3) Uani 1 1 d . . . H1OS H 0.0939(19) 0.2965(17) 0.0366(9) 0.048(5) Uiso 1 1 d . . . C1S C 0.12801(14) 0.13234(12) 0.06874(6) 0.0256(3) Uani 1 1 d . . . H1SB H 0.0301(19) 0.1059(16) 0.0709(8) 0.046(5) Uiso 1 1 d . . . H1SA H 0.1532(18) 0.1018(16) 0.0257(8) 0.044(4) Uiso 1 1 d . . . C2S C 0.23115(16) 0.07689(13) 0.12305(6) 0.0306(3) Uani 1 1 d . . . H2SA H 0.2252(19) -0.0143(18) 0.1240(8) 0.052(5) Uiso 1 1 d . . . H2SB H 0.2106(18) 0.1078(15) 0.1641(8) 0.042(4) Uiso 1 1 d . . . H2SC H 0.333(2) 0.1008(18) 0.1171(9) 0.058(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 0.0170(4) 0.0230(4) 0.0170(4) -0.0012(3) 0.0008(3) 0.0044(3) N1 0.0143(5) 0.0199(5) 0.0180(4) 0.0019(4) 0.0002(3) 0.0008(3) N2 0.0174(5) 0.0217(5) 0.0198(5) 0.0021(4) -0.0008(4) 0.0017(4) N3 0.0167(5) 0.0187(5) 0.0186(4) 0.0005(4) 0.0002(3) 0.0008(3) C1 0.0190(6) 0.0334(7) 0.0270(6) 0.0014(5) 0.0015(5) -0.0029(5) C2 0.0212(6) 0.0233(6) 0.0216(6) -0.0002(5) 0.0019(5) -0.0014(4) C3 0.0163(6) 0.0214(6) 0.0209(5) 0.0001(4) 0.0044(4) -0.0006(4) C4 0.0189(6) 0.0209(6) 0.0203(5) 0.0023(5) 0.0030(4) -0.0012(4) C5 0.0173(6) 0.0184(6) 0.0174(5) 0.0008(4) 0.0031(4) 0.0015(4) C6 0.0224(6) 0.0229(6) 0.0151(5) 0.0019(4) 0.0027(4) 0.0008(4) C7 0.0271(7) 0.0270(6) 0.0148(5) -0.0002(5) -0.0008(5) -0.0002(5) C8 0.0206(6) 0.0305(7) 0.0184(5) 0.0003(5) -0.0024(4) -0.0045(5) C9 0.0186(6) 0.0234(6) 0.0173(5) 0.0008(4) 0.0008(4) -0.0033(4) C10 0.0147(5) 0.0184(5) 0.0158(5) 0.0007(4) 0.0011(4) 0.0017(4) C11 0.0137(5) 0.0174(5) 0.0180(5) -0.0014(4) 0.0018(4) 0.0002(4) C12 0.0169(6) 0.0155(5) 0.0159(5) -0.0016(4) 0.0002(4) 0.0011(4) C13 0.0191(6) 0.0203(6) 0.0127(5) -0.0022(4) 0.0003(4) -0.0023(4) C14 0.0206(6) 0.0234(6) 0.0165(5) 0.0000(4) 0.0014(4) 0.0001(4) C15 0.0196(6) 0.0333(7) 0.0191(5) -0.0035(5) 0.0033(4) -0.0022(5) C16 0.0265(7) 0.0331(7) 0.0213(6) -0.0033(5) 0.0058(5) -0.0114(5) C17 0.0342(7) 0.0216(6) 0.0223(6) 0.0009(5) 0.0027(5) -0.0081(5) C18 0.0238(6) 0.0196(6) 0.0187(5) -0.0012(4) -0.0002(4) -0.0012(5) C19 0.0311(7) 0.0241(6) 0.0195(6) 0.0039(5) -0.0017(5) 0.0052(5) C20 0.0324(7) 0.0345(7) 0.0197(6) 0.0041(5) 0.0070(5) -0.0008(6) O1S 0.0697(7) 0.0230(5) 0.0236(5) -0.0002(4) -0.0191(5) 0.0036(4) C1S 0.0252(7) 0.0241(6) 0.0255(6) 0.0020(5) -0.0045(5) -0.0024(5) C2S 0.0360(8) 0.0274(7) 0.0255(6) -0.0018(5) -0.0075(5) 0.0072(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 C10 1.4316(13) . ? O1 H1O 0.890(18) . ? N1 N2 1.3393(13) . ? N1 C11 1.3578(14) . ? N1 C3 1.4787(14) . ? N2 N3 1.3160(13) . ? N3 C12 1.3672(14) . ? C1 C2 1.3127(18) . ? C1 H1A 0.958(16) . ? C1 H1B 0.972(15) . ? C2 C3 1.4981(15) . ? C2 H2 0.998(15) . ? C3 C4 1.5305(15) . ? C3 H3 1.003(14) . ? C4 C5 1.5264(15) . ? C4 H4A 0.948(13) . ? C4 H4B 0.985(15) . ? C5 C10 1.5530(15) . ? C5 C6 1.5561(14) . ? C5 H5 1.003(13) . ? C6 C19 1.5346(16) . ? C6 C20 1.5358(16) . ? C6 C7 1.5416(16) . ? C7 C8 1.5251(16) . ? C7 H7A 0.997(14) . ? C7 H7B 0.999(14) . ? C8 C9 1.5261(15) . ? C8 H8A 0.978(14) . ? C8 H8B 0.997(15) . ? C9 C10 1.5306(15) . ? C9 H9A 1.001(14) . ? C9 H9B 0.968(14) . ? C10 C11 1.5156(14) . ? C11 C12 1.3846(15) . ? C12 C13 1.4764(15) . ? C13 C18 1.3953(16) . ? C13 C14 1.3973(16) . ? C14 C15 1.3900(17) . ? C14 H14 0.962(14) . ? C15 C16 1.3881(18) . ? C15 H15 0.971(15) . ? C16 C17 1.3870(19) . ? C16 H16 0.974(15) . ? C17 C18 1.3887(17) . ? C17 H17 0.975(16) . ? C18 H18 0.952(14) . ? C19 H19A 1.006(16) . ? C19 H19B 0.998(16) . ? C19 H19C 0.976(16) . ? C20 H20A 1.009(16) . ? C20 H20B 1.001(16) . ? C20 H20C 0.991(15) . ? O1S C1S 1.3981(15) . ? O1S H1OS 0.853(19) . ? C1S C2S 1.5053(16) . ? C1S H1SB 0.952(18) . ? C1S H1SA 1.015(17) . ? C2S H2SA 0.966(19) . ? C2S H2SB 0.965(17) . ? C2S H2SC 1.00(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 C10 O1 H1O 108.9(11) . . ? N2 N1 C11 111.96(9) . . ? N2 N1 C3 120.43(9) . . ? C11 N1 C3 127.61(9) . . ? N3 N2 N1 106.54(8) . . ? N2 N3 C12 109.82(9) . . ? C2 C1 H1A 120.9(9) . . ? C2 C1 H1B 120.7(9) . . ? H1A C1 H1B 118.4(13) . . ? C1 C2 C3 122.55(11) . . ? C1 C2 H2 122.2(8) . . ? C3 C2 H2 115.2(8) . . ? N1 C3 C2 110.52(9) . . ? N1 C3 C4 107.52(9) . . ? C2 C3 C4 113.09(9) . . ? N1 C3 H3 108.1(8) . . ? C2 C3 H3 108.6(8) . . ? C4 C3 H3 108.9(7) . . ? C5 C4 C3 110.10(9) . . ? C5 C4 H4A 111.4(7) . . ? C3 C4 H4A 108.9(7) . . ? C5 C4 H4B 111.8(8) . . ? C3 C4 H4B 106.9(8) . . ? H4A C4 H4B 107.6(11) . . ? C4 C5 C10 109.58(9) . . ? C4 C5 C6 115.56(9) . . ? C10 C5 C6 114.02(9) . . ? C4 C5 H5 106.7(7) . . ? C10 C5 H5 104.4(7) . . ? C6 C5 H5 105.6(7) . . ? C19 C6 C20 107.69(10) . . ? C19 C6 C7 110.76(10) . . ? C20 C6 C7 107.44(9) . . ? C19 C6 C5 113.88(9) . . ? C20 C6 C5 109.09(9) . . ? C7 C6 C5 107.79(9) . . ? C8 C7 C6 114.05(9) . . ? C8 C7 H7A 110.8(8) . . ? C6 C7 H7A 108.6(8) . . ? C8 C7 H7B 107.6(8) . . ? C6 C7 H7B 108.5(8) . . ? H7A C7 H7B 107.2(11) . . ? C7 C8 C9 111.68(10) . . ? C7 C8 H8A 109.9(8) . . ? C9 C8 H8A 109.7(8) . . ? C7 C8 H8B 109.5(8) . . ? C9 C8 H8B 108.5(8) . . ? H8A C8 H8B 107.5(11) . . ? C8 C9 C10 110.64(9) . . ? C8 C9 H9A 109.2(8) . . ? C10 C9 H9A 108.6(8) . . ? C8 C9 H9B 110.0(8) . . ? C10 C9 H9B 110.5(8) . . ? H9A C9 H9B 107.8(11) . . ? O1 C10 C11 108.61(8) . . ? O1 C10 C9 107.06(9) . . ? C11 C10 C9 111.62(9) . . ? O1 C10 C5 111.92(8) . . ? C11 C10 C5 108.80(9) . . ? C9 C10 C5 108.85(9) . . ? N1 C11 C12 103.98(9) . . ? N1 C11 C10 121.52(9) . . ? C12 C11 C10 134.47(10) . . ? N3 C12 C11 107.68(10) . . ? N3 C12 C13 120.31(9) . . ? C11 C12 C13 131.99(10) . . ? C18 C13 C14 119.02(10) . . ? C18 C13 C12 119.79(10) . . ? C14 C13 C12 121.18(10) . . ? C15 C14 C13 120.44(11) . . ? C15 C14 H14 119.8(8) . . ? C13 C14 H14 119.7(8) . . ? C16 C15 C14 119.93(12) . . ? C16 C15 H15 120.6(9) . . ? C14 C15 H15 119.4(9) . . ? C17 C16 C15 120.09(11) . . ? C17 C16 H16 120.2(9) . . ? C15 C16 H16 119.7(9) . . ? C16 C17 C18 120.05(11) . . ? C16 C17 H17 121.0(9) . . ? C18 C17 H17 118.9(9) . . ? C17 C18 C13 120.46(11) . . ? C17 C18 H18 119.9(8) . . ? C13 C18 H18 119.7(8) . . ? C6 C19 H19A 110.1(9) . . ? C6 C19 H19B 112.3(9) . . ? H19A C19 H19B 108.0(12) . . ? C6 C19 H19C 109.5(9) . . ? H19A C19 H19C 108.0(12) . . ? H19B C19 H19C 108.8(12) . . ? C6 C20 H20A 110.1(9) . . ? C6 C20 H20B 112.3(9) . . ? H20A C20 H20B 107.5(12) . . ? C6 C20 H20C 110.4(8) . . ? H20A C20 H20C 107.3(12) . . ? H20B C20 H20C 109.1(12) . . ? C1S O1S H1OS 110.3(12) . . ? O1S C1S C2S 109.29(10) . . ? O1S C1S H1SB 110.4(10) . . ? C2S C1S H1SB 111.0(10) . . ? O1S C1S H1SA 109.1(9) . . ? C2S C1S H1SA 110.8(9) . . ? H1SB C1S H1SA 106.2(14) . . ? C1S C2S H2SA 111.9(11) . . ? C1S C2S H2SB 111.6(10) . . ? H2SA C2S H2SB 107.4(14) . . ? C1S C2S H2SC 108.6(11) . . ? H2SA C2S H2SC 108.2(15) . . ? H2SB C2S H2SC 109.0(14) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C11 N1 N2 N3 0.83(12) . . . . ? C3 N1 N2 N3 -179.34(9) . . . . ? N1 N2 N3 C12 0.08(11) . . . . ? N2 N1 C3 C2 39.46(13) . . . . ? C11 N1 C3 C2 -140.73(11) . . . . ? N2 N1 C3 C4 163.33(9) . . . . ? C11 N1 C3 C4 -16.86(15) . . . . ? C1 C2 C3 N1 -129.27(12) . . . . ? C1 C2 C3 C4 110.14(13) . . . . ? N1 C3 C4 C5 49.52(12) . . . . ? C2 C3 C4 C5 171.80(9) . . . . ? C3 C4 C5 C10 -69.19(11) . . . . ? C3 C4 C5 C6 160.35(9) . . . . ? C4 C5 C6 C19 58.67(13) . . . . ? C10 C5 C6 C19 -69.62(13) . . . . ? C4 C5 C6 C20 -61.65(13) . . . . ? C10 C5 C6 C20 170.06(9) . . . . ? C4 C5 C6 C7 -178.01(9) . . . . ? C10 C5 C6 C7 53.70(12) . . . . ? C19 C6 C7 C8 73.39(12) . . . . ? C20 C6 C7 C8 -169.24(10) . . . . ? C5 C6 C7 C8 -51.80(13) . . . . ? C6 C7 C8 C9 55.40(14) . . . . ? C7 C8 C9 C10 -57.20(13) . . . . ? C8 C9 C10 O1 -63.74(11) . . . . ? C8 C9 C10 C11 177.52(9) . . . . ? C8 C9 C10 C5 57.41(12) . . . . ? C4 C5 C10 O1 -70.90(11) . . . . ? C6 C5 C10 O1 60.38(12) . . . . ? C4 C5 C10 C11 49.13(11) . . . . ? C6 C5 C10 C11 -179.59(9) . . . . ? C4 C5 C10 C9 170.97(9) . . . . ? C6 C5 C10 C9 -57.75(12) . . . . ? N2 N1 C11 C12 -1.35(12) . . . . ? C3 N1 C11 C12 178.83(10) . . . . ? N2 N1 C11 C10 -179.58(9) . . . . ? C3 N1 C11 C10 0.60(16) . . . . ? O1 C10 C11 N1 105.48(11) . . . . ? C9 C10 C11 N1 -136.71(10) . . . . ? C5 C10 C11 N1 -16.58(14) . . . . ? O1 C10 C11 C12 -72.11(15) . . . . ? C9 C10 C11 C12 45.70(16) . . . . ? C5 C10 C11 C12 165.84(12) . . . . ? N2 N3 C12 C11 -0.92(12) . . . . ? N2 N3 C12 C13 177.94(9) . . . . ? N1 C11 C12 N3 1.34(12) . . . . ? C10 C11 C12 N3 179.22(11) . . . . ? N1 C11 C12 C13 -177.33(11) . . . . ? C10 C11 C12 C13 0.5(2) . . . . ? N3 C12 C13 C18 40.71(14) . . . . ? C11 C12 C13 C18 -140.76(12) . . . . ? N3 C12 C13 C14 -137.82(11) . . . . ? C11 C12 C13 C14 40.71(17) . . . . ? C18 C13 C14 C15 1.19(16) . . . . ? C12 C13 C14 C15 179.73(10) . . . . ? C13 C14 C15 C16 -0.73(16) . . . . ? C14 C15 C16 C17 -0.29(17) . . . . ? C15 C16 C17 C18 0.83(17) . . . . ? C16 C17 C18 C13 -0.36(17) . . . . ? C14 C13 C18 C17 -0.64(16) . . . . ? C12 C13 C18 C17 -179.21(10) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1 H1O O1S 0.890(18) 1.853(18) 2.7427(12) 176.4(16) . O1S H1OS N3 0.853(19) 1.908(19) 2.7595(13) 175.5(17) 3_565 O1S H1OS N2 0.853(19) 2.677(19) 3.4379(13) 149.3(15) 3_565 _diffrn_measured_fraction_theta_max 0.936 _diffrn_reflns_theta_full 66.00 _diffrn_measured_fraction_theta_full 0.966 _refine_diff_density_max 0.284 _refine_diff_density_min -0.181 _refine_diff_density_rms 0.032 #===END