# Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is (c) The Royal Society of Chemistry 2009 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_Cambridge 0177 loop_ _publ_author_name _publ_author_address 'Rodolfo Marquez' ? 'James J. Crawford' '' 'Jennifer E. Mathieson' '' 'Marc Schmidtmann' '' _publ_contact_author_name 'Rodolfo Marquez' _publ_contact_author_email R.MARQUEZ@CHEM.GLA.AC.UK _publ_section_title ; Fast and Efficient One Step Synthesis of Dienamides ; _publ_contact_author_address ; Department of Chemistry University of Glasgow Glasgow G12 8QQ UK ; _publ_contact_author_fax 44(141)3308775 _publ_contact_author_phone 44(141)3308522 # Attachment 'jennifer_publ.cif' data_jennifer _database_code_depnum_ccdc_archive 'CCDC 702660' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C15 H23 N O5' _chemical_formula_weight 297.34 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' _cell_length_a 6.1541(12) _cell_length_b 7.9492(16) _cell_length_c 8.6988(17) _cell_angle_alpha 71.93(3) _cell_angle_beta 70.89(3) _cell_angle_gamma 83.00(3) _cell_volume 382.17(13) _cell_formula_units_Z 1 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.292 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 160 _exptl_absorpt_coefficient_mu 0.097 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9716 _exptl_absorpt_correction_T_max 0.9904 _exptl_absorpt_process_details 'fsprocess (Higashi, 2001)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(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 'Rigaku R-Axis Rapid IP area detector' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 14382 _diffrn_reflns_av_R_equivalents 0.0133 _diffrn_reflns_av_sigmaI/netI 0.0190 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 3.15 _diffrn_reflns_theta_max 36.32 _reflns_number_total 6694 _reflns_number_gt 6368 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku/MSC Inc., 2006)' _computing_cell_refinement fsprocess _computing_data_reduction fsprocess _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _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^)+(0.0600P)^2^+0.0200P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.0(4) _chemical_absolute_configuration syn _refine_ls_number_reflns 6694 _refine_ls_number_parameters 199 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0362 _refine_ls_R_factor_gt 0.0345 _refine_ls_wR_factor_ref 0.0950 _refine_ls_wR_factor_gt 0.0933 _refine_ls_goodness_of_fit_ref 1.098 _refine_ls_restrained_S_all 1.098 _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 0.10150(9) 0.82954(8) 0.49920(7) 0.01635(10) Uani 1 1 d . . . O2 O 0.15870(10) 1.13219(8) 0.43558(7) 0.01885(11) Uani 1 1 d . . . O3 O 0.29669(11) 0.61271(9) 0.17952(9) 0.02475(13) Uani 1 1 d . . . O4 O -0.84656(11) 0.50943(11) 0.88778(9) 0.02627(14) Uani 1 1 d . . . O5 O -1.11916(10) 0.43710(9) 0.79914(8) 0.02116(12) Uani 1 1 d . . . N1 N -0.04766(11) 0.61250(9) 0.38566(9) 0.01710(11) Uani 1 1 d . . . C1 C 0.15500(13) 0.96517(10) 0.55763(9) 0.01683(13) Uani 1 1 d . . . C2 C 0.30984(13) 1.13787(11) 0.26959(10) 0.01869(13) Uani 1 1 d . . . H2A H 0.4699 1.1159 0.2739 0.022 Uiso 1 1 calc R . . H2B H 0.3011 1.2575 0.1915 0.022 Uiso 1 1 calc R . . C3 C 0.24987(13) 1.00060(10) 0.19998(9) 0.01647(12) Uani 1 1 d . . . C4 C 0.25046(12) 0.82048(10) 0.33657(9) 0.01495(12) Uani 1 1 d . . . H4A H 0.4104 0.7925 0.3436 0.018 Uiso 1 1 calc R . . C5 C -0.04617(16) 0.97440(13) 0.71234(11) 0.02483(16) Uani 1 1 d . . . H5A H -0.1887 0.9978 0.6814 0.037 Uiso 1 1 calc R . . H5B H -0.0229 1.0698 0.7542 0.037 Uiso 1 1 calc R . . H5C H -0.0571 0.8615 0.8015 0.037 Uiso 1 1 calc R . . C6 C 0.38101(15) 0.92250(12) 0.60169(11) 0.02200(14) Uani 1 1 d . . . H6A H 0.5059 0.9088 0.5016 0.033 Uiso 1 1 calc R . . H6B H 0.3661 0.8122 0.6945 0.033 Uiso 1 1 calc R . . H6C H 0.4156 1.0192 0.6372 0.033 Uiso 1 1 calc R . . C7 C 0.43506(16) 1.00370(13) 0.03160(11) 0.02511(16) Uani 1 1 d . . . H7A H 0.4405 1.1225 -0.0481 0.038 Uiso 1 1 calc R . . H7B H 0.3986 0.9180 -0.0162 0.038 Uiso 1 1 calc R . . H7C H 0.5848 0.9725 0.0511 0.038 Uiso 1 1 calc R . . C8 C 0.01208(15) 1.04418(13) 0.17440(12) 0.02440(16) Uani 1 1 d . . . H8A H 0.0140 1.1609 0.0919 0.037 Uiso 1 1 calc R . . H8B H -0.1034 1.0449 0.2830 0.037 Uiso 1 1 calc R . . H8C H -0.0263 0.9546 0.1320 0.037 Uiso 1 1 calc R . . C9 C 0.17216(13) 0.67064(10) 0.29383(10) 0.01690(12) Uani 1 1 d . . . C10 C -0.14637(14) 0.49197(11) 0.34363(11) 0.01869(13) Uani 1 1 d . . . H10A H -0.0581 0.4557 0.2466 0.022 Uiso 1 1 calc R . . C11 C -0.35597(13) 0.42165(11) 0.42775(11) 0.01917(13) Uani 1 1 d . . . H11A H -0.4034 0.3425 0.3831 0.023 Uiso 1 1 calc R . . C12 C -0.51566(13) 0.45564(10) 0.58001(10) 0.01717(13) Uani 1 1 d . . . H12A H -0.4615 0.5135 0.6405 0.021 Uiso 1 1 calc R . . C13 C -0.73763(13) 0.40868(10) 0.63951(10) 0.01701(13) Uani 1 1 d . . . H13A H -0.7913 0.3431 0.5850 0.020 Uiso 1 1 calc R . . C14 C -0.89847(13) 0.45719(10) 0.78749(10) 0.01747(13) Uani 1 1 d . . . C15 C -1.29237(15) 0.48626(13) 0.93770(11) 0.02356(16) Uani 1 1 d . . . H15A H -1.4455 0.4747 0.9310 0.035 Uiso 1 1 calc R . . H15B H -1.2711 0.6092 0.9299 0.035 Uiso 1 1 calc R . . H15C H -1.2779 0.4083 1.0461 0.035 Uiso 1 1 calc R . . H1 H -0.122(3) 0.646(2) 0.480(2) 0.031(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 0.0171(2) 0.0165(2) 0.0152(2) -0.00602(18) -0.00194(18) -0.00418(18) O2 0.0198(2) 0.0149(2) 0.0195(2) -0.00583(19) -0.0018(2) -0.00129(19) O3 0.0194(3) 0.0307(3) 0.0263(3) -0.0172(3) -0.0008(2) -0.0024(2) O4 0.0204(3) 0.0398(4) 0.0226(3) -0.0135(3) -0.0057(2) -0.0053(2) O5 0.0143(2) 0.0300(3) 0.0193(2) -0.0086(2) -0.00228(19) -0.0048(2) N1 0.0155(2) 0.0190(3) 0.0181(3) -0.0087(2) -0.0032(2) -0.0023(2) C1 0.0177(3) 0.0161(3) 0.0164(3) -0.0058(2) -0.0025(2) -0.0040(2) C2 0.0170(3) 0.0169(3) 0.0187(3) -0.0035(2) -0.0014(2) -0.0033(2) C3 0.0142(3) 0.0182(3) 0.0153(3) -0.0036(2) -0.0031(2) -0.0015(2) C4 0.0133(3) 0.0165(3) 0.0150(3) -0.0054(2) -0.0033(2) -0.0009(2) C5 0.0252(4) 0.0264(4) 0.0199(3) -0.0107(3) 0.0029(3) -0.0068(3) C6 0.0230(3) 0.0233(4) 0.0231(3) -0.0077(3) -0.0095(3) -0.0031(3) C7 0.0239(4) 0.0310(4) 0.0164(3) -0.0064(3) 0.0000(3) -0.0046(3) C8 0.0202(3) 0.0255(4) 0.0260(4) -0.0016(3) -0.0109(3) 0.0002(3) C9 0.0146(3) 0.0186(3) 0.0185(3) -0.0069(2) -0.0048(2) -0.0009(2) C10 0.0162(3) 0.0200(3) 0.0227(3) -0.0104(3) -0.0054(2) -0.0010(2) C11 0.0163(3) 0.0197(3) 0.0239(3) -0.0102(3) -0.0054(3) -0.0009(2) C12 0.0160(3) 0.0163(3) 0.0190(3) -0.0037(2) -0.0062(2) -0.0013(2) C13 0.0151(3) 0.0170(3) 0.0186(3) -0.0049(2) -0.0045(2) -0.0017(2) C14 0.0157(3) 0.0183(3) 0.0170(3) -0.0026(2) -0.0042(2) -0.0038(2) C15 0.0171(3) 0.0306(4) 0.0203(3) -0.0074(3) -0.0007(3) -0.0044(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C4 1.4300(10) . ? O1 C1 1.4370(9) . ? O2 C1 1.4170(11) . ? O2 C2 1.4291(11) . ? O3 C9 1.2194(10) . ? O4 C14 1.2144(10) . ? O5 C14 1.3539(10) . ? O5 C15 1.4460(12) . ? N1 C9 1.3776(11) . ? N1 C10 1.3875(10) . ? N1 H1 0.899(16) . ? C1 C5 1.5157(12) . ? C1 C6 1.5330(12) . ? C2 C3 1.5323(11) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C7 1.5284(13) . ? C3 C8 1.5338(12) . ? C3 C4 1.5519(12) . ? C4 C9 1.5235(11) . ? C4 H4A 1.0000 . ? 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 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C10 C11 1.3475(12) . ? C10 H10A 0.9500 . ? C11 C12 1.4485(12) . ? C11 H11A 0.9500 . ? C12 C13 1.3471(11) . ? C12 H12A 0.9500 . ? C13 C14 1.4717(12) . ? C13 H13A 0.9500 . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 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 C4 O1 C1 114.79(6) . . ? C1 O2 C2 113.93(7) . . ? C14 O5 C15 115.56(7) . . ? C9 N1 C10 120.94(7) . . ? C9 N1 H1 119.1(10) . . ? C10 N1 H1 119.7(10) . . ? O2 C1 O1 110.08(6) . . ? O2 C1 C5 105.93(8) . . ? O1 C1 C5 105.89(7) . . ? O2 C1 C6 111.97(7) . . ? O1 C1 C6 111.40(7) . . ? C5 C1 C6 111.27(7) . . ? O2 C2 C3 112.17(7) . . ? O2 C2 H2A 109.2 . . ? C3 C2 H2A 109.2 . . ? O2 C2 H2B 109.2 . . ? C3 C2 H2B 109.2 . . ? H2A C2 H2B 107.9 . . ? C7 C3 C2 108.13(7) . . ? C7 C3 C8 110.74(7) . . ? C2 C3 C8 109.98(7) . . ? C7 C3 C4 111.50(7) . . ? C2 C3 C4 105.31(6) . . ? C8 C3 C4 111.01(7) . . ? O1 C4 C9 108.29(6) . . ? O1 C4 C3 110.52(6) . . ? C9 C4 C3 111.95(6) . . ? O1 C4 H4A 108.7 . . ? C9 C4 H4A 108.7 . . ? C3 C4 H4A 108.7 . . ? C1 C5 H5A 109.5 . . ? C1 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? C1 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? C1 C6 H6A 109.5 . . ? C1 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C1 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 . . ? C3 C8 H8A 109.5 . . ? C3 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C3 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? O3 C9 N1 123.05(7) . . ? O3 C9 C4 120.71(7) . . ? N1 C9 C4 116.17(7) . . ? C11 C10 N1 125.98(7) . . ? C11 C10 H10A 117.0 . . ? N1 C10 H10A 117.0 . . ? C10 C11 C12 126.00(7) . . ? C10 C11 H11A 117.0 . . ? C12 C11 H11A 117.0 . . ? C13 C12 C11 122.83(7) . . ? C13 C12 H12A 118.6 . . ? C11 C12 H12A 118.6 . . ? C12 C13 C14 121.12(7) . . ? C12 C13 H13A 119.4 . . ? C14 C13 H13A 119.4 . . ? O4 C14 O5 122.94(8) . . ? O4 C14 C13 126.13(7) . . ? O5 C14 C13 110.93(7) . . ? O5 C15 H15A 109.5 . . ? O5 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? O5 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 36.32 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.444 _refine_diff_density_min -0.187 _refine_diff_density_rms 0.048