# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2009 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Fushun Liang' _publ_contact_author_email LIANGFS112@NENU.EDU.CN _publ_section_title ; Efficient three-component one-pot synthesis of fully substituted pyridin-2(1H)-ones via tandem Knoevenagel condensation/ring-opening of cyclopropane/intramolecular cyclization ; loop_ _publ_author_name 'Fushun Liang.' 'Xin Cheng.' 'Jing Liu.' 'Qun Liu.' # Attachment '4b.cif' data_4b _database_code_depnum_ccdc_archive 'CCDC 714333' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H19 N3 O2' _chemical_formula_weight 309.36 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting ? _symmetry_space_group_name_H-M ? loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y, -z-1/2' '-x-1/2, y-1/2, z' 'x, -y-1/2, z-1/2' _cell_length_a 9.790(2) _cell_length_b 13.973(3) _cell_length_c 23.768(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3251.4(13) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.264 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1312 _exptl_absorpt_coefficient_mu 0.084 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 17041 _diffrn_reflns_av_R_equivalents 0.0323 _diffrn_reflns_av_sigmaI/netI 0.0238 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 2.68 _diffrn_reflns_theta_max 26.05 _reflns_number_total 3196 _reflns_number_gt 2202 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _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^)+(0.0953P)^2^+1.0777P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3196 _refine_ls_number_parameters 211 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0853 _refine_ls_R_factor_gt 0.0596 _refine_ls_wR_factor_ref 0.1858 _refine_ls_wR_factor_gt 0.1645 _refine_ls_goodness_of_fit_ref 1.040 _refine_ls_restrained_S_all 1.040 _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 0.1324(2) 0.39575(18) 0.63121(11) 0.0578(6) Uani 1 1 d . . . C2 C 0.2338(2) 0.46880(17) 0.60865(10) 0.0558(6) Uani 1 1 d . . . C3 C 0.1693(3) 0.55229(17) 0.57881(10) 0.0554(6) Uani 1 1 d . . . C4 C 0.0350(2) 0.55325(15) 0.56818(9) 0.0504(6) Uani 1 1 d . . . C5 C -0.0591(2) 0.47674(15) 0.58450(9) 0.0469(5) Uani 1 1 d . . . C6 C 0.3334(3) 0.4143(2) 0.56801(13) 0.0703(7) Uani 1 1 d . . . H6A H 0.3037 0.3486 0.5629 0.084 Uiso 1 1 calc R . . H6B H 0.3360 0.4453 0.5315 0.084 Uiso 1 1 calc R . . C7 C 0.4698(4) 0.4171(5) 0.5948(3) 0.167(2) Uani 1 1 d . . . H7A H 0.5102 0.3537 0.5942 0.200 Uiso 1 1 calc R . . H7B H 0.5291 0.4600 0.5740 0.200 Uiso 1 1 calc R . . C8 C 0.4577(4) 0.4490(3) 0.6511(2) 0.1224(16) Uani 1 1 d . . . H8A H 0.5335 0.4909 0.6603 0.147 Uiso 1 1 calc R . . H8B H 0.4605 0.3946 0.6765 0.147 Uiso 1 1 calc R . . C9 C 0.3271(3) 0.5010(2) 0.65819(14) 0.0792(9) Uani 1 1 d . . . H9A H 0.3422 0.5696 0.6569 0.095 Uiso 1 1 calc R . . H9B H 0.2854 0.4850 0.6940 0.095 Uiso 1 1 calc R . . C10 C -0.0970(2) 0.33315(16) 0.64056(9) 0.0478(5) Uani 1 1 d . . . C11 C -0.1759(3) 0.35289(17) 0.68688(10) 0.0583(6) Uani 1 1 d . . . H11 H -0.1666 0.4112 0.7054 0.070 Uiso 1 1 calc R . . C12 C -0.2697(3) 0.28593(18) 0.70608(11) 0.0609(7) Uani 1 1 d . . . H12 H -0.3238 0.2994 0.7373 0.073 Uiso 1 1 calc R . . C13 C -0.2822(2) 0.19965(17) 0.67874(11) 0.0567(6) Uani 1 1 d . . . C14 C -0.2015(3) 0.18020(17) 0.63219(11) 0.0612(7) Uani 1 1 d . . . H14 H -0.2098 0.1218 0.6138 0.073 Uiso 1 1 calc R . . C15 C -0.1096(2) 0.24689(17) 0.61323(11) 0.0562(6) Uani 1 1 d . . . H15 H -0.0558 0.2338 0.5819 0.067 Uiso 1 1 calc R . . C16 C -0.4819(3) 0.1544(3) 0.72935(15) 0.0957(11) Uani 1 1 d . . . H16A H -0.5361 0.0987 0.7370 0.144 Uiso 1 1 calc R . . H16B H -0.5373 0.2017 0.7110 0.144 Uiso 1 1 calc R . . H16C H -0.4475 0.1800 0.7641 0.144 Uiso 1 1 calc R . . C17 C 0.2608(3) 0.6317(2) 0.55907(13) 0.0795(9) Uani 1 1 d . . . H17A H 0.3531 0.6186 0.5704 0.119 Uiso 1 1 calc R . . H17B H 0.2315 0.6911 0.5754 0.119 Uiso 1 1 calc R . . H17C H 0.2564 0.6362 0.5188 0.119 Uiso 1 1 calc R . . C18 C -0.0254(3) 0.63131(18) 0.53723(11) 0.0595(6) Uani 1 1 d . . . N1 N -0.00412(18) 0.40543(13) 0.61948(8) 0.0491(5) Uani 1 1 d . . . N2 N -0.1815(2) 0.47865(15) 0.56688(9) 0.0584(6) Uani 1 1 d . . . N3 N -0.0695(3) 0.69388(18) 0.51261(11) 0.0829(8) Uani 1 1 d . . . O1 O 0.1716(2) 0.32824(16) 0.65929(9) 0.0880(7) Uani 1 1 d . . . O2 O -0.3716(2) 0.12934(14) 0.69416(9) 0.0810(6) Uani 1 1 d . . . H2N H -0.229(3) 0.424(2) 0.5807(13) 0.097 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 0.0483(14) 0.0633(15) 0.0618(15) 0.0127(12) -0.0097(11) -0.0016(11) C2 0.0437(13) 0.0577(14) 0.0659(15) 0.0052(11) -0.0059(11) -0.0052(10) C3 0.0533(14) 0.0484(12) 0.0644(15) -0.0014(11) -0.0007(11) -0.0065(11) C4 0.0536(14) 0.0437(11) 0.0539(13) -0.0013(10) 0.0003(10) 0.0008(10) C5 0.0448(13) 0.0434(11) 0.0527(13) -0.0030(10) -0.0009(10) 0.0028(9) C6 0.0597(16) 0.0581(15) 0.093(2) 0.0027(14) 0.0064(14) -0.0039(13) C7 0.061(2) 0.243(7) 0.197(5) -0.072(5) -0.017(3) 0.046(3) C8 0.072(2) 0.112(3) 0.184(5) -0.024(3) -0.055(3) 0.014(2) C9 0.0638(18) 0.0836(19) 0.090(2) -0.0024(16) -0.0252(15) -0.0069(15) C10 0.0433(12) 0.0468(12) 0.0533(13) 0.0045(10) -0.0015(10) -0.0003(9) C11 0.0624(15) 0.0541(13) 0.0585(15) -0.0056(11) 0.0044(12) -0.0028(12) C12 0.0600(15) 0.0659(15) 0.0567(14) -0.0004(12) 0.0118(12) -0.0034(13) C13 0.0495(13) 0.0545(13) 0.0660(15) 0.0086(11) 0.0024(11) -0.0058(11) C14 0.0609(15) 0.0479(13) 0.0748(16) -0.0073(12) 0.0055(13) -0.0062(11) C15 0.0509(13) 0.0567(14) 0.0609(15) -0.0049(11) 0.0066(11) 0.0007(11) C16 0.074(2) 0.097(2) 0.116(3) 0.019(2) 0.0306(19) -0.0144(18) C17 0.0686(18) 0.0620(16) 0.108(2) 0.0113(15) -0.0043(16) -0.0186(14) C18 0.0595(15) 0.0499(13) 0.0690(16) 0.0055(12) 0.0040(12) -0.0007(12) N1 0.0421(11) 0.0478(10) 0.0573(11) 0.0052(8) -0.0015(8) -0.0019(8) N2 0.0460(12) 0.0546(12) 0.0747(14) 0.0057(10) -0.0059(10) 0.0012(9) N3 0.0840(17) 0.0641(14) 0.1007(19) 0.0229(14) 0.0060(14) 0.0145(13) O1 0.0594(12) 0.0977(15) 0.1067(16) 0.0506(13) -0.0145(11) -0.0037(11) O2 0.0725(12) 0.0670(11) 0.1035(15) 0.0040(11) 0.0245(11) -0.0175(10) _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 O1 1.217(3) . ? C1 N1 1.372(3) . ? C1 C2 1.521(3) . ? C2 C3 1.504(3) . ? C2 C9 1.557(4) . ? C2 C6 1.570(4) . ? C3 C4 1.339(4) . ? C3 C17 1.502(3) . ? C4 C18 1.443(3) . ? C4 C5 1.464(3) . ? C5 N2 1.269(3) . ? C5 N1 1.405(3) . ? C6 C7 1.481(5) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 C8 1.415(6) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 C9 1.481(5) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 C11 1.373(3) . ? C10 C15 1.375(3) . ? C10 N1 1.448(3) . ? C11 C12 1.388(3) . ? C11 H11 0.9300 . ? C12 C13 1.375(4) . ? C12 H12 0.9300 . ? C13 O2 1.366(3) . ? C13 C14 1.386(4) . ? C14 C15 1.372(3) . ? C14 H14 0.9300 . ? C15 H15 0.9300 . ? C16 O2 1.410(4) . ? C16 H16A 0.9600 . ? C16 H16B 0.9600 . ? C16 H16C 0.9600 . ? C17 H17A 0.9600 . ? C17 H17B 0.9600 . ? C17 H17C 0.9600 . ? C18 N3 1.137(3) . ? N2 H2N 0.96(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 C1 N1 119.7(2) . . ? O1 C1 C2 120.5(2) . . ? N1 C1 C2 119.8(2) . . ? C3 C2 C1 114.4(2) . . ? C3 C2 C9 112.3(2) . . ? C1 C2 C9 108.1(2) . . ? C3 C2 C6 110.3(2) . . ? C1 C2 C6 107.2(2) . . ? C9 C2 C6 104.0(2) . . ? C4 C3 C17 121.3(2) . . ? C4 C3 C2 120.6(2) . . ? C17 C3 C2 118.0(2) . . ? C3 C4 C18 120.4(2) . . ? C3 C4 C5 124.1(2) . . ? C18 C4 C5 115.4(2) . . ? N2 C5 N1 124.9(2) . . ? N2 C5 C4 119.4(2) . . ? N1 C5 C4 115.69(19) . . ? C7 C6 C2 106.4(3) . . ? C7 C6 H6A 110.4 . . ? C2 C6 H6A 110.4 . . ? C7 C6 H6B 110.4 . . ? C2 C6 H6B 110.4 . . ? H6A C6 H6B 108.6 . . ? C8 C7 C6 109.9(3) . . ? C8 C7 H7A 109.7 . . ? C6 C7 H7A 109.7 . . ? C8 C7 H7B 109.7 . . ? C6 C7 H7B 109.7 . . ? H7A C7 H7B 108.2 . . ? C7 C8 C9 109.5(3) . . ? C7 C8 H8A 109.8 . . ? C9 C8 H8A 109.8 . . ? C7 C8 H8B 109.8 . . ? C9 C8 H8B 109.8 . . ? H8A C8 H8B 108.2 . . ? C8 C9 C2 106.2(3) . . ? C8 C9 H9A 110.5 . . ? C2 C9 H9A 110.5 . . ? C8 C9 H9B 110.5 . . ? C2 C9 H9B 110.5 . . ? H9A C9 H9B 108.7 . . ? C11 C10 C15 120.3(2) . . ? C11 C10 N1 119.4(2) . . ? C15 C10 N1 120.3(2) . . ? C10 C11 C12 120.0(2) . . ? C10 C11 H11 120.0 . . ? C12 C11 H11 120.0 . . ? C13 C12 C11 119.6(2) . . ? C13 C12 H12 120.2 . . ? C11 C12 H12 120.2 . . ? O2 C13 C12 124.1(2) . . ? O2 C13 C14 116.0(2) . . ? C12 C13 C14 119.9(2) . . ? C15 C14 C13 120.2(2) . . ? C15 C14 H14 119.9 . . ? C13 C14 H14 119.9 . . ? C14 C15 C10 119.9(2) . . ? C14 C15 H15 120.0 . . ? C10 C15 H15 120.0 . . ? O2 C16 H16A 109.5 . . ? O2 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? O2 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C3 C17 H17A 109.5 . . ? C3 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C3 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? N3 C18 C4 178.1(3) . . ? C1 N1 C5 124.30(19) . . ? C1 N1 C10 118.19(18) . . ? C5 N1 C10 117.31(18) . . ? C5 N2 H2N 109.1(19) . . ? C13 O2 C16 118.1(2) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 C1 C2 C3 -175.2(3) . . . . ? N1 C1 C2 C3 5.3(3) . . . . ? O1 C1 C2 C9 -49.4(3) . . . . ? N1 C1 C2 C9 131.1(2) . . . . ? O1 C1 C2 C6 62.1(3) . . . . ? N1 C1 C2 C6 -117.3(2) . . . . ? C1 C2 C3 C4 -7.5(3) . . . . ? C9 C2 C3 C4 -131.1(3) . . . . ? C6 C2 C3 C4 113.5(3) . . . . ? C1 C2 C3 C17 175.4(2) . . . . ? C9 C2 C3 C17 51.8(3) . . . . ? C6 C2 C3 C17 -63.7(3) . . . . ? C17 C3 C4 C18 0.0(4) . . . . ? C2 C3 C4 C18 -177.1(2) . . . . ? C17 C3 C4 C5 177.8(2) . . . . ? C2 C3 C4 C5 0.8(4) . . . . ? C3 C4 C5 N2 -171.8(2) . . . . ? C18 C4 C5 N2 6.2(3) . . . . ? C3 C4 C5 N1 8.3(3) . . . . ? C18 C4 C5 N1 -173.8(2) . . . . ? C3 C2 C6 C7 121.0(4) . . . . ? C1 C2 C6 C7 -113.9(4) . . . . ? C9 C2 C6 C7 0.4(4) . . . . ? C2 C6 C7 C8 12.0(6) . . . . ? C6 C7 C8 C9 -20.4(7) . . . . ? C7 C8 C9 C2 20.0(5) . . . . ? C3 C2 C9 C8 -131.1(3) . . . . ? C1 C2 C9 C8 101.8(3) . . . . ? C6 C2 C9 C8 -11.9(3) . . . . ? C15 C10 C11 C12 -0.5(4) . . . . ? N1 C10 C11 C12 177.2(2) . . . . ? C10 C11 C12 C13 0.5(4) . . . . ? C11 C12 C13 O2 -179.7(2) . . . . ? C11 C12 C13 C14 -0.1(4) . . . . ? O2 C13 C14 C15 179.4(2) . . . . ? C12 C13 C14 C15 -0.2(4) . . . . ? C13 C14 C15 C10 0.2(4) . . . . ? C11 C10 C15 C14 0.1(4) . . . . ? N1 C10 C15 C14 -177.5(2) . . . . ? C3 C4 C18 N3 4(9) . . . . ? C5 C4 C18 N3 -174(100) . . . . ? O1 C1 N1 C5 -175.6(2) . . . . ? C2 C1 N1 C5 3.9(4) . . . . ? O1 C1 N1 C10 -0.9(4) . . . . ? C2 C1 N1 C10 178.5(2) . . . . ? N2 C5 N1 C1 169.5(2) . . . . ? C4 C5 N1 C1 -10.6(3) . . . . ? N2 C5 N1 C10 -5.2(3) . . . . ? C4 C5 N1 C10 174.69(19) . . . . ? C11 C10 N1 C1 103.0(3) . . . . ? C15 C10 N1 C1 -79.3(3) . . . . ? C11 C10 N1 C5 -81.9(3) . . . . ? C15 C10 N1 C5 95.7(3) . . . . ? C12 C13 O2 C16 18.1(4) . . . . ? C14 C13 O2 C16 -161.5(3) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.319 _refine_diff_density_min -0.219 _refine_diff_density_rms 0.042