# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _publ_contact_author_name 'Ilya Lyapkalo' _publ_contact_author_email ILYA.LYAPKALO@UOCHB.CAS.CZ _publ_section_title ; N-Trimethylsilyloxy-enamines as New Aldehyde Enolate Synthons: General, Efficient and Diastereoselective Aldol Reaction with Ketals and Acetals Induced by Trimethylsilyl Trifluoromethanesulfonate ; loop_ _publ_author_name 'Ilya Lyapkalo' 'Ivana Cisaoovab' 'Manoj R. Sonawane' # Attachment 'X-ray_structures.cif' data_2m _database_code_depnum_ccdc_archive 'CCDC 755320' #TrackingRef 'X-ray_structures.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C16 H25 N O3' _chemical_formula_sum 'C16 H25 N O3' _chemical_formula_weight 279.37 _chemical_compound_source 'synthesized by the authors' 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' _symmetry_space_group_name_Hall '-P 2ybc' 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 5.81100(10) _cell_length_b 13.6360(3) _cell_length_c 21.0230(5) _cell_angle_alpha 90.00 _cell_angle_beta 100.9640(13) _cell_angle_gamma 90.00 _cell_volume 1635.43(6) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 3912 _cell_measurement_theta_min 1 _cell_measurement_theta_max 27.5 _exptl_crystal_description bar _exptl_crystal_colour colourless _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.1 _exptl_crystal_size_min 0.1 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.135 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 608 _exptl_absorpt_coefficient_mu 0.077 _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(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD area detector' _diffrn_measurement_method '\f and \w scans to fill the Ewald sphere' _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 25986 _diffrn_reflns_av_R_equivalents 0.037 _diffrn_reflns_av_sigmaI/netI 0.0251 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 1.79 _diffrn_reflns_theta_max 27.49 _reflns_number_total 3772 _reflns_number_gt 2980 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'COLLECT (Hooft, 1998) and DENZO (Otwinowski & Minor, 1997)' _computing_cell_refinement 'COLLECT and DENZO' _computing_data_reduction 'COLLECT and DENZO' _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0485P)^2^+0.2392P] 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 none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3772 _refine_ls_number_parameters 191 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0511 _refine_ls_R_factor_gt 0.0378 _refine_ls_wR_factor_ref 0.1019 _refine_ls_wR_factor_gt 0.0948 _refine_ls_goodness_of_fit_ref 1.053 _refine_ls_restrained_S_all 1.053 _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 C1 C -0.04730(18) 0.81032(8) 0.35394(5) 0.0268(2) Uani 1 1 d . . . N2 N -0.22814(14) 0.86534(6) 0.35510(4) 0.02529(19) Uani 1 1 d . . . C3 C -0.21154(18) 0.97454(8) 0.36851(5) 0.0297(2) Uani 1 1 d . . . O4 O -0.43987(12) 0.82997(6) 0.34734(4) 0.03265(19) Uani 1 1 d . . . C5 C -0.2985(2) 0.98878(10) 0.43194(6) 0.0425(3) Uani 1 1 d . . . H5A H -0.1953 0.9535 0.4668 0.064 Uiso 1 1 calc R . . H5B H -0.4584 0.9632 0.4273 0.064 Uiso 1 1 calc R . . H5C H -0.2976 1.0588 0.4425 0.064 Uiso 1 1 calc R . . C6 C 0.0382(2) 1.01206(9) 0.37555(7) 0.0403(3) Uani 1 1 d . . . H6A H 0.0970 0.9982 0.3358 0.060 Uiso 1 1 calc R . . H6B H 0.1379 0.9792 0.4122 0.060 Uiso 1 1 calc R . . H6C H 0.0409 1.0830 0.3832 0.060 Uiso 1 1 calc R . . C7 C -0.3686(2) 1.02538(9) 0.31197(6) 0.0419(3) Uani 1 1 d . . . H7A H -0.5265 0.9973 0.3058 0.063 Uiso 1 1 calc R . . H7B H -0.3045 1.0160 0.2725 0.063 Uiso 1 1 calc R . . H7C H -0.3760 1.0956 0.3212 0.063 Uiso 1 1 calc R . . C8 C -0.07174(18) 0.70225(8) 0.34462(5) 0.0284(2) Uani 1 1 d . . . H8 H -0.1984 0.6788 0.3671 0.034 Uiso 1 1 calc R . . C9 C 0.15928(18) 0.65414(7) 0.37701(5) 0.0280(2) Uani 1 1 d . . . H9 H 0.2899 0.6826 0.3581 0.034 Uiso 1 1 calc R . . C10 C 0.21068(17) 0.67051(7) 0.44955(5) 0.0278(2) Uani 1 1 d . . . C11 C 0.06792(19) 0.62917(8) 0.48816(5) 0.0338(3) Uani 1 1 d . . . H11 H -0.0645 0.5918 0.4684 0.041 Uiso 1 1 calc R . . C12 C 0.1136(2) 0.64094(9) 0.55501(6) 0.0366(3) Uani 1 1 d . . . H12 H 0.0141 0.6116 0.5806 0.044 Uiso 1 1 calc R . . C13 C 0.3052(2) 0.69576(8) 0.58393(5) 0.0336(3) Uani 1 1 d . . . C14 C 0.4493(2) 0.73856(8) 0.54605(6) 0.0370(3) Uani 1 1 d . . . H14 H 0.5800 0.7769 0.5658 0.044 Uiso 1 1 calc R . . C15 C 0.40289(18) 0.72549(8) 0.47956(6) 0.0327(2) Uani 1 1 d . . . H15 H 0.5034 0.7544 0.4541 0.039 Uiso 1 1 calc R . . O16 O 0.13825(13) 0.55201(5) 0.36136(4) 0.03306(19) Uani 1 1 d . . . C17 C 0.3545(2) 0.50152(9) 0.37946(6) 0.0432(3) Uani 1 1 d . . . H17A H 0.3995 0.5001 0.4268 0.065 Uiso 1 1 calc R . . H17B H 0.4759 0.5353 0.3612 0.065 Uiso 1 1 calc R . . H17C H 0.3372 0.4342 0.3629 0.065 Uiso 1 1 calc R . . C18 C -0.1405(2) 0.67567(9) 0.27264(6) 0.0405(3) Uani 1 1 d . . . H18A H -0.0092 0.6898 0.2509 0.061 Uiso 1 1 calc R . . H18B H -0.2772 0.7145 0.2527 0.061 Uiso 1 1 calc R . . H18C H -0.1790 0.6057 0.2683 0.061 Uiso 1 1 calc R . . O19 O 0.36888(16) 0.71034(6) 0.64957(4) 0.0436(2) Uani 1 1 d . . . C20 C 0.2382(3) 0.65900(11) 0.69001(6) 0.0493(3) Uani 1 1 d . . . H20A H 0.2407 0.5886 0.6808 0.074 Uiso 1 1 calc R . . H20B H 0.0758 0.6824 0.6814 0.074 Uiso 1 1 calc R . . H20C H 0.3083 0.6707 0.7356 0.074 Uiso 1 1 calc R . . H1 H 0.100(2) 0.8411(9) 0.3591(5) 0.029(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 C1 0.0241(5) 0.0267(5) 0.0287(5) 0.0030(4) 0.0026(4) -0.0008(4) N2 0.0215(4) 0.0274(4) 0.0258(4) 0.0031(3) 0.0016(3) -0.0015(3) C3 0.0254(5) 0.0257(5) 0.0365(6) -0.0011(4) 0.0023(4) 0.0016(4) O4 0.0207(4) 0.0370(4) 0.0389(4) 0.0032(3) 0.0023(3) -0.0054(3) C5 0.0363(6) 0.0471(7) 0.0435(7) -0.0111(6) 0.0062(5) 0.0034(5) C6 0.0306(6) 0.0290(6) 0.0601(8) -0.0025(5) 0.0060(5) -0.0037(5) C7 0.0391(7) 0.0324(6) 0.0502(7) 0.0071(5) -0.0014(5) 0.0046(5) C8 0.0275(5) 0.0249(5) 0.0322(6) 0.0025(4) 0.0041(4) -0.0017(4) C9 0.0289(5) 0.0233(5) 0.0323(6) 0.0018(4) 0.0068(4) 0.0000(4) C10 0.0278(5) 0.0230(5) 0.0320(6) 0.0031(4) 0.0043(4) 0.0033(4) C11 0.0329(6) 0.0347(6) 0.0331(6) 0.0000(5) 0.0045(4) -0.0050(5) C12 0.0387(6) 0.0384(6) 0.0337(6) 0.0028(5) 0.0091(5) -0.0007(5) C13 0.0406(6) 0.0267(5) 0.0311(6) -0.0012(4) 0.0009(5) 0.0075(5) C14 0.0364(6) 0.0289(6) 0.0419(7) -0.0015(5) -0.0019(5) -0.0029(5) C15 0.0311(5) 0.0279(6) 0.0385(6) 0.0042(5) 0.0049(5) -0.0011(4) O16 0.0369(4) 0.0234(4) 0.0389(4) -0.0004(3) 0.0073(3) 0.0033(3) C17 0.0450(7) 0.0345(6) 0.0510(7) 0.0004(5) 0.0110(6) 0.0130(5) C18 0.0485(7) 0.0337(6) 0.0349(6) -0.0011(5) -0.0035(5) -0.0005(5) O19 0.0577(5) 0.0393(5) 0.0308(4) -0.0046(3) 0.0002(4) 0.0033(4) C20 0.0592(8) 0.0580(9) 0.0312(6) -0.0029(6) 0.0097(6) 0.0112(7) _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 C1 N2 1.2951(13) . ? C1 C8 1.4899(14) . ? C1 H1 0.942(12) . ? N2 O4 1.3026(10) . ? N2 C3 1.5153(13) . ? C3 C6 1.5194(15) . ? C3 C7 1.5209(16) . ? C3 C5 1.5258(17) . ? C5 H5A 0.9800 . ? C5 H5B 0.9800 . ? C5 H5C 0.9800 . ? C6 H6A 0.9800 . ? C6 H6B 0.9800 . ? C6 H6C 0.9800 . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? C8 C9 1.5325(14) . ? C8 C18 1.5332(16) . ? C8 H8 1.0000 . ? C9 O16 1.4308(12) . ? C9 C10 1.5138(15) . ? C9 H9 1.0000 . ? C10 C11 1.3859(15) . ? C10 C15 1.3927(15) . ? C11 C12 1.3890(16) . ? C11 H11 0.9500 . ? C12 C13 1.3820(16) . ? C12 H12 0.9500 . ? C13 O19 1.3736(14) . ? C13 C14 1.3892(18) . ? C14 C15 1.3838(17) . ? C14 H14 0.9500 . ? C15 H15 0.9500 . ? O16 C17 1.4197(14) . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? O19 C20 1.4266(17) . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C20 H20C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N2 C1 C8 121.20(9) . . ? N2 C1 H1 117.6(7) . . ? C8 C1 H1 121.2(7) . . ? C1 N2 O4 122.25(9) . . ? C1 N2 C3 123.34(8) . . ? O4 N2 C3 114.35(8) . . ? N2 C3 C6 112.01(8) . . ? N2 C3 C7 107.16(9) . . ? C6 C3 C7 110.05(10) . . ? N2 C3 C5 105.52(9) . . ? C6 C3 C5 109.94(10) . . ? C7 C3 C5 112.07(10) . . ? C3 C5 H5A 109.5 . . ? C3 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? C3 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? C3 C6 H6A 109.5 . . ? C3 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C3 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? C3 C7 H7A 109.5 . . ? C3 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C3 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C1 C8 C9 108.15(8) . . ? C1 C8 C18 111.34(9) . . ? C9 C8 C18 112.28(9) . . ? C1 C8 H8 108.3 . . ? C9 C8 H8 108.3 . . ? C18 C8 H8 108.3 . . ? O16 C9 C10 111.53(8) . . ? O16 C9 C8 106.57(8) . . ? C10 C9 C8 111.89(8) . . ? O16 C9 H9 108.9 . . ? C10 C9 H9 108.9 . . ? C8 C9 H9 108.9 . . ? C11 C10 C15 118.13(10) . . ? C11 C10 C9 120.30(9) . . ? C15 C10 C9 121.55(9) . . ? C10 C11 C12 121.67(10) . . ? C10 C11 H11 119.2 . . ? C12 C11 H11 119.2 . . ? C13 C12 C11 119.38(11) . . ? C13 C12 H12 120.3 . . ? C11 C12 H12 120.3 . . ? O19 C13 C12 124.13(11) . . ? O19 C13 C14 115.99(10) . . ? C12 C13 C14 119.87(11) . . ? C15 C14 C13 120.13(10) . . ? C15 C14 H14 119.9 . . ? C13 C14 H14 119.9 . . ? C14 C15 C10 120.82(11) . . ? C14 C15 H15 119.6 . . ? C10 C15 H15 119.6 . . ? C17 O16 C9 112.20(9) . . ? O16 C17 H17A 109.5 . . ? O16 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? O16 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C8 C18 H18A 109.5 . . ? C8 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C8 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C13 O19 C20 117.08(10) . . ? O19 C20 H20A 109.5 . . ? O19 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? O19 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.159 _refine_diff_density_min -0.170 _refine_diff_density_rms 0.036 #===END data_2p _database_code_depnum_ccdc_archive 'CCDC 755321' #TrackingRef 'X-ray_structures.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C21 H27 N O3' _chemical_formula_sum 'C21 H27 N O3' _chemical_formula_weight 341.44 _chemical_compound_source 'synthesized by the authors' 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' _symmetry_space_group_name_Hall "-P 2ybc'" 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 16.1659(5) _cell_length_b 5.6972(2) _cell_length_c 20.6824(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.5706(18) _cell_angle_gamma 90.00 _cell_volume 1904.76(10) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 4645 _cell_measurement_theta_min 1 _cell_measurement_theta_max 27.5 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.4 _exptl_crystal_size_min 0.35 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.191 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 736 _exptl_absorpt_coefficient_mu 0.079 _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(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD area detector' _diffrn_measurement_method '\f and \w scans to fill the Ewald sphere' _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 25374 _diffrn_reflns_av_R_equivalents 0.047 _diffrn_reflns_av_sigmaI/netI 0.0446 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 1.97 _diffrn_reflns_theta_max 27.48 _reflns_number_total 4372 _reflns_number_gt 2807 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'COLLECT (Hooft, 1998) and DENZO (Otwinowski & Minor, 1997)' _computing_cell_refinement 'COLLECT and DENZO' _computing_data_reduction 'COLLECT and DENZO' _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0682P)^2^+0.0000P] 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 0.0090(13) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 4372 _refine_ls_number_parameters 236 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0771 _refine_ls_R_factor_gt 0.0417 _refine_ls_wR_factor_ref 0.1173 _refine_ls_wR_factor_gt 0.1038 _refine_ls_goodness_of_fit_ref 0.976 _refine_ls_restrained_S_all 0.976 _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 C1 C 0.29115(8) 0.9697(2) 0.64188(6) 0.0275(3) Uani 1 1 d . . . N2 N 0.34101(6) 0.79374(17) 0.63641(5) 0.0263(3) Uani 1 1 d . . . C3 C 0.43315(7) 0.8251(2) 0.62435(6) 0.0303(3) Uani 1 1 d . . . O4 O 0.31620(5) 0.57578(14) 0.63644(4) 0.0348(2) Uani 1 1 d . . . C5 C 0.44776(9) 0.7220(3) 0.55735(6) 0.0416(4) Uani 1 1 d . . . H5A H 0.5065 0.7348 0.5468 0.062 Uiso 1 1 calc R . . H5B H 0.4148 0.8085 0.5253 0.062 Uiso 1 1 calc R . . H5C H 0.4313 0.5564 0.5570 0.062 Uiso 1 1 calc R . . C6 C 0.45798(9) 1.0817(2) 0.62574(8) 0.0443(4) Uani 1 1 d . . . H6A H 0.5176 1.0952 0.6184 0.066 Uiso 1 1 calc R . . H6B H 0.4446 1.1490 0.6680 0.066 Uiso 1 1 calc R . . H6C H 0.4278 1.1667 0.5917 0.066 Uiso 1 1 calc R . . C7 C 0.47981(8) 0.6935(2) 0.67731(7) 0.0374(3) Uani 1 1 d . . . H7A H 0.4699 0.7692 0.7191 0.056 Uiso 1 1 calc R . . H7B H 0.5392 0.6958 0.6681 0.056 Uiso 1 1 calc R . . H7C H 0.4604 0.5306 0.6788 0.056 Uiso 1 1 calc R . . C8 C 0.19912(7) 0.9419(2) 0.64137(6) 0.0289(3) Uani 1 1 d . . . H8 H 0.1857 0.7781 0.6274 0.035 Uiso 1 1 calc R . . C9 C 0.16525(7) 1.1125(2) 0.58978(6) 0.0305(3) Uani 1 1 d . . . H9 H 0.1746 1.2771 0.6050 0.037 Uiso 1 1 calc R . . C10 C 0.20797(7) 1.0796(2) 0.52556(6) 0.0284(3) Uani 1 1 d . . . C11 C 0.26167(8) 1.2485(2) 0.50185(6) 0.0318(3) Uani 1 1 d . . . H11 H 0.2714 1.3879 0.5259 0.038 Uiso 1 1 calc R . . C12 C 0.30126(8) 1.2158(2) 0.44340(6) 0.0347(3) Uani 1 1 d . . . H12 H 0.3379 1.3326 0.4278 0.042 Uiso 1 1 calc R . . C13 C 0.28764(8) 1.0140(2) 0.40781(6) 0.0321(3) Uani 1 1 d . . . C14 C 0.23544(8) 0.8413(2) 0.43085(6) 0.0332(3) Uani 1 1 d . . . H14 H 0.2265 0.7012 0.4069 0.040 Uiso 1 1 calc R . . C15 C 0.19634(8) 0.8764(2) 0.48971(6) 0.0317(3) Uani 1 1 d . . . H15 H 0.1607 0.7579 0.5058 0.038 Uiso 1 1 calc R . . O16 O 0.07844(5) 1.07081(18) 0.58540(4) 0.0406(3) Uani 1 1 d . . . C17 C 0.03709(9) 1.2451(3) 0.54796(7) 0.0556(5) Uani 1 1 d . . . H17A H 0.0564 1.2382 0.5032 0.083 Uiso 1 1 calc R . . H17B H 0.0491 1.4006 0.5661 0.083 Uiso 1 1 calc R . . H17C H -0.0227 1.2167 0.5488 0.083 Uiso 1 1 calc R . . C18 C 0.16008(7) 0.9836(2) 0.70699(6) 0.0287(3) Uani 1 1 d . . . C19 C 0.17840(8) 1.1845(2) 0.74254(6) 0.0336(3) Uani 1 1 d . . . H19 H 0.2165 1.2962 0.7262 0.040 Uiso 1 1 calc R . . C20 C 0.14126(8) 1.2225(3) 0.80192(6) 0.0384(3) Uani 1 1 d . . . H20 H 0.1539 1.3602 0.8260 0.046 Uiso 1 1 calc R . . C21 C 0.08605(8) 1.0609(3) 0.82606(6) 0.0405(4) Uani 1 1 d . . . H21 H 0.0610 1.0872 0.8668 0.049 Uiso 1 1 calc R . . C22 C 0.06708(8) 0.8613(3) 0.79125(7) 0.0405(4) Uani 1 1 d . . . H22 H 0.0290 0.7500 0.8078 0.049 Uiso 1 1 calc R . . C23 C 0.10416(8) 0.8239(2) 0.73169(6) 0.0350(3) Uani 1 1 d . . . H23 H 0.0909 0.6866 0.7076 0.042 Uiso 1 1 calc R . . O24 O 0.32772(6) 1.00244(18) 0.34962(4) 0.0420(3) Uani 1 1 d . . . C25 C 0.31005(10) 0.8050(3) 0.30893(7) 0.0502(4) Uani 1 1 d . . . H25A H 0.2500 0.7854 0.3047 0.075 Uiso 1 1 calc R . . H25B H 0.3343 0.6632 0.3281 0.075 Uiso 1 1 calc R . . H25C H 0.3338 0.8314 0.2661 0.075 Uiso 1 1 calc R . . H1 H 0.3150(8) 1.124(2) 0.6428(6) 0.033(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 C1 0.0284(7) 0.0259(7) 0.0283(7) -0.0015(6) -0.0003(5) 0.0011(6) N2 0.0286(6) 0.0232(6) 0.0272(5) -0.0001(5) -0.0002(4) -0.0014(5) C3 0.0244(7) 0.0275(7) 0.0390(7) 0.0019(6) 0.0023(5) 0.0011(5) O4 0.0365(5) 0.0219(5) 0.0459(5) -0.0007(4) 0.0022(4) -0.0036(4) C5 0.0374(8) 0.0494(9) 0.0383(8) -0.0007(7) 0.0086(6) 0.0018(7) C6 0.0287(8) 0.0318(8) 0.0723(10) 0.0050(7) -0.0004(7) -0.0022(6) C7 0.0326(8) 0.0350(8) 0.0446(8) 0.0021(7) -0.0041(6) 0.0024(6) C8 0.0273(7) 0.0275(7) 0.0318(7) -0.0022(6) -0.0008(5) -0.0008(5) C9 0.0261(7) 0.0348(7) 0.0305(7) -0.0024(6) -0.0003(5) 0.0032(6) C10 0.0247(7) 0.0314(7) 0.0291(6) -0.0001(6) -0.0020(5) 0.0050(5) C11 0.0313(7) 0.0316(7) 0.0324(7) -0.0031(6) -0.0019(6) 0.0013(6) C12 0.0311(7) 0.0374(8) 0.0357(7) 0.0014(6) 0.0009(6) -0.0034(6) C13 0.0258(7) 0.0439(8) 0.0267(6) -0.0004(6) -0.0009(5) 0.0050(6) C14 0.0314(7) 0.0356(8) 0.0325(7) -0.0064(6) -0.0034(6) 0.0025(6) C15 0.0284(7) 0.0345(8) 0.0323(7) 0.0005(6) -0.0006(5) -0.0005(6) O16 0.0250(5) 0.0610(7) 0.0359(5) 0.0008(5) -0.0013(4) 0.0064(4) C17 0.0399(9) 0.0829(13) 0.0438(9) 0.0027(8) -0.0038(7) 0.0263(8) C18 0.0242(7) 0.0318(7) 0.0301(7) 0.0024(6) -0.0022(5) 0.0024(6) C19 0.0328(7) 0.0353(8) 0.0326(7) -0.0002(6) 0.0002(6) -0.0035(6) C20 0.0384(8) 0.0439(9) 0.0328(7) -0.0043(7) -0.0004(6) 0.0003(7) C21 0.0383(8) 0.0524(9) 0.0308(7) 0.0038(7) 0.0041(6) 0.0037(7) C22 0.0326(8) 0.0456(9) 0.0433(8) 0.0086(7) 0.0049(6) -0.0027(7) C23 0.0302(7) 0.0349(8) 0.0399(7) 0.0006(6) -0.0009(6) -0.0016(6) O24 0.0356(5) 0.0591(7) 0.0315(5) -0.0074(5) 0.0054(4) -0.0014(5) C25 0.0475(9) 0.0656(11) 0.0375(8) -0.0161(8) 0.0046(7) 0.0063(8) _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 C1 N2 1.2919(15) . ? C1 C8 1.4962(17) . ? C1 H1 0.962(13) . ? N2 O4 1.3049(12) . ? N2 C3 1.5232(15) . ? C3 C6 1.5162(19) . ? C3 C7 1.5215(17) . ? C3 C5 1.5256(18) . ? C5 H5A 0.9800 . ? C5 H5B 0.9800 . ? C5 H5C 0.9800 . ? C6 H6A 0.9800 . ? C6 H6B 0.9800 . ? C6 H6C 0.9800 . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? C8 C18 1.5210(16) . ? C8 C9 1.5400(18) . ? C8 H8 1.0000 . ? C9 O16 1.4253(15) . ? C9 C10 1.5149(16) . ? C9 H9 1.0000 . ? C10 C15 1.3862(18) . ? C10 C11 1.3888(18) . ? C11 C12 1.3860(17) . ? C11 H11 0.9500 . ? C12 C13 1.3816(18) . ? C12 H12 0.9500 . ? C13 O24 1.3741(14) . ? C13 C14 1.3837(18) . ? C14 C15 1.3916(17) . ? C14 H14 0.9500 . ? C15 H15 0.9500 . ? O16 C17 1.4219(17) . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C18 C23 1.3842(18) . ? C18 C19 1.3906(18) . ? C19 C20 1.3893(17) . ? C19 H19 0.9500 . ? C20 C21 1.379(2) . ? C20 H20 0.9500 . ? C21 C22 1.379(2) . ? C21 H21 0.9500 . ? C22 C23 1.3917(18) . ? C22 H22 0.9500 . ? C23 H23 0.9500 . ? O24 C25 1.4318(17) . ? C25 H25A 0.9800 . ? C25 H25B 0.9800 . ? C25 H25C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N2 C1 C8 122.58(12) . . ? N2 C1 H1 117.6(8) . . ? C8 C1 H1 119.7(8) . . ? C1 N2 O4 123.11(11) . . ? C1 N2 C3 122.37(10) . . ? O4 N2 C3 114.38(9) . . ? C6 C3 C7 109.41(11) . . ? C6 C3 N2 111.66(10) . . ? C7 C3 N2 107.63(10) . . ? C6 C3 C5 110.19(11) . . ? C7 C3 C5 112.59(11) . . ? N2 C3 C5 105.32(10) . . ? C3 C5 H5A 109.5 . . ? C3 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? C3 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? C3 C6 H6A 109.5 . . ? C3 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C3 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? C3 C7 H7A 109.5 . . ? C3 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C3 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C1 C8 C18 113.49(10) . . ? C1 C8 C9 106.54(10) . . ? C18 C8 C9 111.81(10) . . ? C1 C8 H8 108.3 . . ? C18 C8 H8 108.3 . . ? C9 C8 H8 108.3 . . ? O16 C9 C10 112.39(10) . . ? O16 C9 C8 106.38(10) . . ? C10 C9 C8 111.55(10) . . ? O16 C9 H9 108.8 . . ? C10 C9 H9 108.8 . . ? C8 C9 H9 108.8 . . ? C15 C10 C11 118.14(11) . . ? C15 C10 C9 120.79(11) . . ? C11 C10 C9 121.05(11) . . ? C12 C11 C10 120.69(12) . . ? C12 C11 H11 119.7 . . ? C10 C11 H11 119.7 . . ? C13 C12 C11 120.27(12) . . ? C13 C12 H12 119.9 . . ? C11 C12 H12 119.9 . . ? O24 C13 C12 115.62(12) . . ? O24 C13 C14 124.20(12) . . ? C12 C13 C14 120.17(11) . . ? C13 C14 C15 118.87(12) . . ? C13 C14 H14 120.6 . . ? C15 C14 H14 120.6 . . ? C10 C15 C14 121.84(12) . . ? C10 C15 H15 119.1 . . ? C14 C15 H15 119.1 . . ? C17 O16 C9 112.06(11) . . ? O16 C17 H17A 109.5 . . ? O16 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? O16 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C23 C18 C19 118.84(11) . . ? C23 C18 C8 120.31(11) . . ? C19 C18 C8 120.83(11) . . ? C20 C19 C18 120.27(12) . . ? C20 C19 H19 119.9 . . ? C18 C19 H19 119.9 . . ? C21 C20 C19 120.18(13) . . ? C21 C20 H20 119.9 . . ? C19 C20 H20 119.9 . . ? C22 C21 C20 120.20(12) . . ? C22 C21 H21 119.9 . . ? C20 C21 H21 119.9 . . ? C21 C22 C23 119.53(13) . . ? C21 C22 H22 120.2 . . ? C23 C22 H22 120.2 . . ? C18 C23 C22 120.97(13) . . ? C18 C23 H23 119.5 . . ? C22 C23 H23 119.5 . . ? C13 O24 C25 117.35(11) . . ? O24 C25 H25A 109.5 . . ? O24 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? O24 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.198 _refine_diff_density_min -0.176 _refine_diff_density_rms 0.039 #===END data_2s _database_code_depnum_ccdc_archive 'CCDC 755322' #TrackingRef 'X-ray_structures.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C16 H25 N O2' _chemical_formula_sum 'C16 H25 N O2' _chemical_formula_weight 263.37 _chemical_compound_source 'synthesized by the authors' 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' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 5.9484(2) _cell_length_b 8.4271(3) _cell_length_c 15.9289(5) _cell_angle_alpha 93.4557(15) _cell_angle_beta 95.3665(18) _cell_angle_gamma 106.3773(17) _cell_volume 759.58(4) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 3400 _cell_measurement_theta_min 1 _cell_measurement_theta_max 27.5 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.4 _exptl_crystal_size_min 0.3 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.152 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 288 _exptl_absorpt_coefficient_mu 0.075 _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(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD area detector' _diffrn_measurement_method '\f and \w scans to fill the Ewald sphere' _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 15912 _diffrn_reflns_av_R_equivalents 0.024 _diffrn_reflns_av_sigmaI/netI 0.0207 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 1.29 _diffrn_reflns_theta_max 27.48 _reflns_number_total 3462 _reflns_number_gt 3032 _reflns_threshold_expression I>\2s(I) _computing_data_collection 'COLLECT (Hooft, 1998) and DENZO (Otwinowski & Minor, 1997)' _computing_cell_refinement 'COLLECT and DENZO' _computing_data_reduction 'COLLECT and DENZO' _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0487P)^2^+0.1937P] 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 none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3462 _refine_ls_number_parameters 182 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0429 _refine_ls_R_factor_gt 0.0373 _refine_ls_wR_factor_ref 0.1016 _refine_ls_wR_factor_gt 0.0979 _refine_ls_goodness_of_fit_ref 1.036 _refine_ls_restrained_S_all 1.036 _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 C1 C 0.82949(17) 0.99728(12) 0.33000(6) 0.0215(2) Uani 1 1 d . . . N2 N 0.64491(14) 0.90888(10) 0.36077(5) 0.02015(18) Uani 1 1 d . . . C3 C 0.64723(17) 0.75867(12) 0.40826(6) 0.0230(2) Uani 1 1 d . . . O4 O 0.43837(12) 0.93224(9) 0.34703(5) 0.02816(18) Uani 1 1 d . . . C5 C 0.4986(2) 0.61055(13) 0.34812(8) 0.0350(3) Uani 1 1 d . . . H5A H 0.3397 0.6215 0.3350 0.052 Uiso 1 1 calc R . . H5B H 0.4887 0.5076 0.3751 0.052 Uiso 1 1 calc R . . H5C H 0.5720 0.6075 0.2957 0.052 Uiso 1 1 calc R . . C6 C 0.89519(19) 0.74508(14) 0.42932(7) 0.0310(2) Uani 1 1 d . . . H6A H 0.9653 0.7339 0.3768 0.047 Uiso 1 1 calc R . . H6B H 0.8885 0.6474 0.4605 0.047 Uiso 1 1 calc R . . H6C H 0.9917 0.8452 0.4642 0.047 Uiso 1 1 calc R . . C7 C 0.5351(2) 0.77461(15) 0.48931(7) 0.0327(3) Uani 1 1 d . . . H7A H 0.6318 0.8732 0.5252 0.049 Uiso 1 1 calc R . . H7B H 0.5249 0.6756 0.5197 0.049 Uiso 1 1 calc R . . H7C H 0.3764 0.7853 0.4751 0.049 Uiso 1 1 calc R . . C8 C 0.80825(17) 1.12523(12) 0.27127(6) 0.0229(2) Uani 1 1 d . . . H8 H 0.6380 1.0969 0.2483 0.028 Uiso 1 1 calc R . . C9 C 0.94747(18) 1.11284(12) 0.19458(6) 0.0236(2) Uani 1 1 d . . . C10 C 0.87828(18) 0.92903(13) 0.16104(6) 0.0241(2) Uani 1 1 d . . . C11 C 0.6532(2) 0.85441(15) 0.11840(7) 0.0320(2) Uani 1 1 d . . . H11 H 0.5520 0.9208 0.1047 0.038 Uiso 1 1 calc R . . C12 C 0.5758(2) 0.68450(16) 0.09579(8) 0.0382(3) Uani 1 1 d . . . H12 H 0.4222 0.6357 0.0668 0.046 Uiso 1 1 calc R . . C13 C 0.7206(2) 0.58533(15) 0.11510(7) 0.0360(3) Uani 1 1 d . . . H13 H 0.6662 0.4688 0.1004 0.043 Uiso 1 1 calc R . . C14 C 0.9450(2) 0.65790(14) 0.15603(7) 0.0317(2) Uani 1 1 d . . . H14 H 1.0463 0.5911 0.1687 0.038 Uiso 1 1 calc R . . C15 C 1.02377(19) 0.82842(13) 0.17885(6) 0.0263(2) Uani 1 1 d . . . H15 H 1.1785 0.8767 0.2069 0.032 Uiso 1 1 calc R . . O16 O 0.85607(14) 1.20752(10) 0.13503(5) 0.03069(19) Uani 1 1 d . . . C17 C 0.9595(3) 1.22246(18) 0.05805(8) 0.0474(4) Uani 1 1 d . . . H17A H 1.1267 1.2853 0.0698 0.071 Uiso 1 1 calc R . . H17B H 0.8784 1.2808 0.0198 0.071 Uiso 1 1 calc R . . H17C H 0.9450 1.1116 0.0314 0.071 Uiso 1 1 calc R . . C18 C 0.8725(2) 1.29850(13) 0.31868(8) 0.0343(3) Uani 1 1 d . . . H18A H 0.7607 1.3002 0.3599 0.051 Uiso 1 1 calc R . . H18B H 0.8654 1.3805 0.2782 0.051 Uiso 1 1 calc R . . H18C H 1.0325 1.3256 0.3482 0.051 Uiso 1 1 calc R . . C19 C 1.21243(19) 1.18852(13) 0.21727(7) 0.0300(2) Uani 1 1 d . . . H19A H 1.2947 1.1627 0.1701 0.045 Uiso 1 1 calc R . . H19B H 1.2646 1.1423 0.2680 0.045 Uiso 1 1 calc R . . H19C H 1.2485 1.3093 0.2283 0.045 Uiso 1 1 calc R . . H1 H 0.976(2) 0.9725(15) 0.3448(8) 0.027(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 C1 0.0213(5) 0.0209(5) 0.0226(5) 0.0033(4) 0.0032(3) 0.0062(4) N2 0.0198(4) 0.0203(4) 0.0212(4) 0.0032(3) 0.0026(3) 0.0068(3) C3 0.0229(5) 0.0207(5) 0.0262(5) 0.0075(4) 0.0040(4) 0.0062(4) O4 0.0198(4) 0.0340(4) 0.0350(4) 0.0123(3) 0.0061(3) 0.0119(3) C5 0.0398(6) 0.0209(5) 0.0398(6) 0.0048(4) -0.0009(5) 0.0029(4) C6 0.0278(5) 0.0316(6) 0.0383(6) 0.0138(5) 0.0054(4) 0.0134(4) C7 0.0347(6) 0.0400(6) 0.0301(5) 0.0150(5) 0.0116(4) 0.0169(5) C8 0.0237(5) 0.0217(5) 0.0261(5) 0.0066(4) 0.0068(4) 0.0086(4) C9 0.0261(5) 0.0234(5) 0.0255(5) 0.0079(4) 0.0068(4) 0.0111(4) C10 0.0270(5) 0.0261(5) 0.0219(5) 0.0050(4) 0.0063(4) 0.0103(4) C11 0.0308(6) 0.0373(6) 0.0299(5) 0.0013(4) 0.0000(4) 0.0148(5) C12 0.0342(6) 0.0409(7) 0.0342(6) -0.0058(5) -0.0011(5) 0.0060(5) C13 0.0457(7) 0.0279(6) 0.0328(6) -0.0028(4) 0.0094(5) 0.0076(5) C14 0.0403(6) 0.0293(6) 0.0313(5) 0.0056(4) 0.0104(5) 0.0167(5) C15 0.0280(5) 0.0275(5) 0.0266(5) 0.0053(4) 0.0056(4) 0.0117(4) O16 0.0399(4) 0.0337(4) 0.0282(4) 0.0137(3) 0.0118(3) 0.0216(3) C17 0.0715(9) 0.0557(8) 0.0333(6) 0.0224(6) 0.0238(6) 0.0387(7) C18 0.0475(7) 0.0230(5) 0.0355(6) 0.0054(4) 0.0170(5) 0.0110(5) C19 0.0277(5) 0.0259(5) 0.0387(6) 0.0082(4) 0.0112(4) 0.0080(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 C1 N2 1.2977(13) . ? C1 C8 1.4934(13) . ? C1 H1 0.963(13) . ? N2 O4 1.2990(10) . ? N2 C3 1.5160(12) . ? C3 C6 1.5194(14) . ? C3 C7 1.5234(14) . ? C3 C5 1.5272(15) . ? C5 H5A 0.9800 . ? C5 H5B 0.9800 . ? C5 H5C 0.9800 . ? C6 H6A 0.9800 . ? C6 H6B 0.9800 . ? C6 H6C 0.9800 . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? C8 C18 1.5320(14) . ? C8 C9 1.5529(13) . ? C8 H8 1.0000 . ? C9 O16 1.4393(11) . ? C9 C19 1.5232(15) . ? C9 C10 1.5343(14) . ? C10 C15 1.3947(14) . ? C10 C11 1.3973(15) . ? C11 C12 1.3882(17) . ? C11 H11 0.9500 . ? C12 C13 1.3867(18) . ? C12 H12 0.9500 . ? C13 C14 1.3819(17) . ? C13 H13 0.9500 . ? C14 C15 1.3936(15) . ? C14 H14 0.9500 . ? C15 H15 0.9500 . ? O16 C17 1.4192(13) . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N2 C1 C8 120.37(9) . . ? N2 C1 H1 116.9(7) . . ? C8 C1 H1 122.6(7) . . ? C1 N2 O4 122.92(8) . . ? C1 N2 C3 122.53(8) . . ? O4 N2 C3 114.27(7) . . ? N2 C3 C6 112.25(8) . . ? N2 C3 C7 107.56(8) . . ? C6 C3 C7 110.08(9) . . ? N2 C3 C5 104.51(8) . . ? C6 C3 C5 110.52(9) . . ? C7 C3 C5 111.80(9) . . ? C3 C5 H5A 109.5 . . ? C3 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? C3 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? C3 C6 H6A 109.5 . . ? C3 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C3 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? C3 C7 H7A 109.5 . . ? C3 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C3 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C1 C8 C18 111.30(8) . . ? C1 C8 C9 110.22(8) . . ? C18 C8 C9 114.62(8) . . ? C1 C8 H8 106.7 . . ? C18 C8 H8 106.7 . . ? C9 C8 H8 106.7 . . ? O16 C9 C19 110.57(8) . . ? O16 C9 C10 110.59(8) . . ? C19 C9 C10 113.19(8) . . ? O16 C9 C8 102.59(7) . . ? C19 C9 C8 112.26(9) . . ? C10 C9 C8 107.09(8) . . ? C15 C10 C11 118.11(10) . . ? C15 C10 C9 122.14(9) . . ? C11 C10 C9 119.43(9) . . ? C12 C11 C10 120.79(10) . . ? C12 C11 H11 119.6 . . ? C10 C11 H11 119.6 . . ? C13 C12 C11 120.57(11) . . ? C13 C12 H12 119.7 . . ? C11 C12 H12 119.7 . . ? C14 C13 C12 119.24(11) . . ? C14 C13 H13 120.4 . . ? C12 C13 H13 120.4 . . ? C13 C14 C15 120.44(10) . . ? C13 C14 H14 119.8 . . ? C15 C14 H14 119.8 . . ? C14 C15 C10 120.84(10) . . ? C14 C15 H15 119.6 . . ? C10 C15 H15 119.6 . . ? C17 O16 C9 115.16(8) . . ? O16 C17 H17A 109.5 . . ? O16 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? O16 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C8 C18 H18A 109.5 . . ? C8 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C8 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C9 C19 H19A 109.5 . . ? C9 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C9 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.273 _refine_diff_density_min -0.187 _refine_diff_density_rms 0.035 #===END