# Supplementary Material (ESI) for Perkin Transactions # This journal is © The Royal Society of Chemistry 2002 data_19b _database_code_CSD 183665 _journal_coden_Cambridge 207 _publ_requested_journal 'Perkin Transactions 1' loop_ _publ_author_name 'Fujii, Nobutaka' 'Ajito, Keiichi' 'Hamanaka, Nobuyuki' 'Kamano, Takae' 'Miwa, Yoshihisa' 'Niida, Ayumu' 'Odagaki, Yoshihiko' 'Oishi, Shinya' 'Otaka, Akira' 'Taga, Tooru' 'Tamamura, Hirokazu' 'Yamamoto, Mikio' _publ_contact_author_name 'Prof Nobutaka Fujii' _publ_contact_author_address ; Graduate School of Pharmaceutical Sciences Kyoto University Sakyo-ku Kyoto 606-8501 JAPAN ; _publ_contact_author_email 'NFUJII@PHARM.KYOTO-U.AC.JP' _publ_section_title ; Regio- and stereoselective ring-opening of chiral 1,3-oxazolidin-2-one derivatives by organocopper reagents provides novel access to di-, tri- and tetra-substituted alkene dipeptide isosteres ; _chemical_name_common 19b _chemical_formula_sum 'C26 H41 O4 N1' _chemical_formula_weight 431.62 _chemical_compound_source synthetic _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21' loop_ _symmetry_equiv_pos_as_xyz '+X,+Y,+Z' '-X,1/2+Y,-Z' _cell_length_a 10.483(3) _cell_length_b 10.019(2) _cell_length_c 13.104(4) _cell_angle_alpha 90 _cell_angle_beta 90.12(2) _cell_angle_gamma 90 _cell_volume 1376.3 _cell_formula_units_Z 2 _cell_measurement_temperature 295.0 _cell_measurement_reflns_used 25 _cell_measurement_theta_min 22.6 _cell_measurement_theta_max 28.9 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.30 _exptl_crystal_density_diffrn 1.041 _exptl_crystal_F_000 466 _exptl_absorpt_coefficient_mu 0.55 _exptl_absorpt_correction_type none _diffrn_special_details ; \q scan width (1.84 + 0.30tan\q)\%, \q scan rate 8.0\% per min.Background counts for 5 s on each side every scan. ; _diffrn_ambient_temperature 295.0 _diffrn_radiation_wavelength 1.54051 _diffrn_radiation_type CU _diffrn_radiation_source rotarix _diffrn_radiation_monochromator graphaite _diffrn_measurement_device diffractometer _diffrn_measurement_method \q/2\q _diffrn_standards_number 3 _diffrn_standards_interval_count 56 _diffrn_standards_decay_% 2 _diffrn_reflns_number 2229 _diffrn_reflns_av_R_equivalents 0.035 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1 _diffrn_reflns_theta_max 60 _diffrn_reflns_reduction_process NSC/AFC _reflns_number_total 2105 _reflns_observed_criterion F>3\s(F) _computing_data_collection Rigaku/AFC5 _computing_cell_refinement NSC/AFC _computing_data_reduction NSC/AFC _computing_structure_solution 'MULTAN88' _computing_structure_refinement 'Full Matrix Least Squares' _computing_molecular_graphics KPPXRAY _computing_publication_material EDCIF-J _refine_ls_structure_factor_coef F _refine_ls_matrix_type full _refine_ls_weighting_scheme 'calc w=1/(\s^2^(F)+0.023)' _refine_ls_hydrogen_treatment 'refxyz from D-map' _refine_ls_extinction_method none _refine_ls_number_reflns 1897 _refine_ls_number_parameters 403 _refine_ls_R_factor_obs 0.061 _refine_ls_wR_factor_obs 0.077 _refine_ls_goodness_of_fit_obs 1.15 _refine_ls_shift/esd_max 0.08 _refine_diff_density_max 0.18 _refine_diff_density_min -0.24 loop_ _atom_type_symbol _atom_type_oxidation_number _atom_type_number_in_cell _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C 0 52 0.017 0.009 International_Tables_Vol_IV_Table_2.2B H 0 76 0.000 0.000 International_Tables_Vol_IV_Table_2.2B O 0 8 0.047 0.032 International_Tables_Vol_IV_Table_2.2B N 0 2 0.029 0.018 International_Tables_Vol_IV_Table_2.2B loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_thermal_displace_type C1 0.3077(7) 0.547(2) 0.5782(5) .066(3) Ueq C2 0.4412(6) 0.520(2) 0.6181(5) .058(2) Ueq C3 0.4375(6) 0.555(2) 0.7333(5) .053(2) Ueq C4 0.4380(6) 0.462(1) 0.8056(5) .054(2) Ueq C5 0.4280(6) 0.496(1) 0.9175(4) .051(2) Ueq C6 0.3004(7) 0.455(2) 0.9621(5) .063(3) Ueq C7 0.4247(9) 0.704(2) 0.7544(6) .084(3) Ueq C8 0.4419(8) 0.313(2) 0.7822(6) .075(3) Ueq C9 0.5442(7) 0.589(2) 0.5591(6) .078(3) Ueq C10 0.5489(9) 0.538(2) 0.4480(6) .110(5) Ueq C11 0.6747(9) 0.572(2) 0.6099(7) .111(4) Ueq C12 0.2782(6) 0.500(2) 1.0690(5) .054(2) Ueq C13 0.2543(7) 0.636(2) 1.0893(6) .068(3) Ueq C14 0.2372(8) 0.680(2) 1.1877(6) .079(3) Ueq C15 0.2405(8) 0.593(2) 1.2669(6) .085(3) Ueq C16 0.2597(9) 0.460(2) 1.2490(6) .092(4) Ueq C17 0.2789(7) 0.413(2) 1.1516(6) .075(3) Ueq C18 0.0904(8) 0.458(2) 0.5998(6) .085(3) Ueq C19 0.0455(8) 0.469(2) 0.4915(7) .119(5) Ueq C20 0.0478(9) 0.578(2) 0.6627(8) .117(4) Ueq C21 0.044(1) 0.335(2) 0.650(1) .166(6) Ueq C22 0.6362(6) 0.503(2) 0.9987(5) .056(2) Ueq C23 0.8495(8) 0.471(2) 1.0740(7) .087(3) Ueq C24 0.851(1) 0.589(2) 1.142(1) .152(5) Ueq C25 0.911(1) 0.354(2) 1.1237(9) .128(5) Ueq C26 0.921(1) 0.501(2) 0.979(1) .170(7) Ueq N1 0.5321(5) 0.437(1) 0.9764(4) .056(2) Ueq O1 0.2286(5) 0.447(1) 0.6034(4) .077(2) Ueq O2 0.2737(5) 0.648(1) 0.5340(4) .091(2) Ueq O3 0.7218(4) 0.426(1) 1.0484(3) .065(2) Ueq O4 0.6542(6) 0.619(1) 0.9788(5) .107(3) Ueq H1N 0.519(5) 0.350(5) 1.000(4) .05(1) Uiso H2 0.462(4) 0.427(5) 0.609(3) .05(1) Uiso H5 0.437(4) 0.596(5) 0.923(3) .05(1) Uiso H6A 0.229(5) 0.496(5) 0.918(3) .06(1) Uiso H6B 0.293(5) 0.361(6) 0.960(4) .06(1) Uiso H7A 0.427(5) 0.755(6) 0.688(4) .08(1) Uiso H7B 0.496(5) 0.737(6) 0.798(4) .08(1) Uiso H7C 0.342(6) 0.725(6) 0.790(4) .08(1) Uiso H8A 0.451(6) 0.299(6) 0.707(4) .09(3) Uiso H8B 0.362(6) 0.268(6) 0.807(4) .08(1) Uiso H8C 0.517(6) 0.275(6) 0.818(4) .09(1) Uiso H9 0.520(5) 0.689(6) 0.559(4) .09(1) Uiso H10A 0.616(6) 0.590(7) 0.410(5) .10(3) Uiso H10B 0.466(6) 0.557(7) 0.415(5) .10(3) Uiso H10C 0.567(6) 0.447(8) 0.447(4) .11(3) Uiso H11A 0.741(6) 0.621(8) 0.568(5) .11(3) Uiso H11B 0.697(6) 0.479(8) 0.612(5) .11(3) Uiso H11C 0.676(6) 0.609(8) 0.680(5) .11(3) Uiso H13 0.248(5) 0.701(6) 1.033(4) .08(1) Uiso H14 0.218(5) 0.775(6) 1.203(4) .09(3) Uiso H15 0.229(5) 0.625(6) 1.336(4) .09(3) Uiso H16 0.258(6) 0.398(7) 1.308(4) .10(3) Uiso H17 0.288(5) 0.321(6) 1.141(4) .08(1) Uiso H19A -0.047(7) 0.475(8) 0.491(5) .11(3) Uiso H19B 0.078(7) 0.391(8) 0.455(5) .11(3) Uiso H19C 0.082(6) 0.551(8) 0.460(5) .11(3) Uiso H20A -0.045(7) 0.586(7) 0.661(5) .13(3) Uiso H20B 0.089(7) 0.664(7) 0.631(5) .13(3) Uiso H20C 0.076(7) 0.573(7) 0.736(5) .13(3) Uiso H21A -0.046(8) 0.340(9) 0.649(7) .15(4) Uiso H21B 0.074(8) 0.328(9) 0.721(6) .15(4) Uiso H21C 0.074(9) 0.263(9) 0.613(7) .16(4) Uiso H24A 0.815(8) 0.669(9) 1.107(6) .15(3) Uiso H24B 0.943(8) 0.611(9) 1.164(6) .14(3) Uiso H24C 0.802(7) 0.567(9) 1.206(6) .14(3) Uiso H25A 0.911(7) 0.279(7) 1.075(5) .11(3) Uiso H25B 0.865(7) 0.333(7) 1.183(5) .11(3) Uiso H25C 1.000(7) 0.378(8) 1.143(5) .11(3) Uiso H26A 0.918(8) 0.42(1) 0.937(6) .16(4) Uiso H26B 1.012(9) 0.525(9) 0.991(6) .15(3) Uiso H26C 0.878(8) 0.57(1) 0.940(6) .16(4) Uiso loop_ _atom_site_aniso_label _atom_site_aniso_u_11 _atom_site_aniso_u_22 _atom_site_aniso_u_33 _atom_site_aniso_u_12 _atom_site_aniso_u_13 _atom_site_aniso_u_23 C1 .065(4) .082(5) .050(3) -.012(4) .001(3) -.001(3) C2 .059(4) .061(4) .055(3) -.002(3) -.002(3) .001(3) C3 .057(3) .057(4) .043(3) -.002(3) -.001(3) -.002(3) C4 .057(3) .045(4) .061(3) .002(3) -.008(3) -.009(3) C5 .053(3) .047(4) .054(3) .002(3) .000(3) -.001(3) C6 .067(4) .058(5) .063(4) -.001(4) -.007(3) .006(4) C7 .134(8) .054(4) .064(4) .009(4) .001(4) .001(3) C8 .099(5) .055(4) .070(4) .001(4) -.018(3) -.006(3) C9 .070(5) .087(6) .077(4) -.008(4) .008(3) .005(4) C10 .105(7) .15(1) .070(6) .001(6) .026(5) .012(6) C11 .079(6) .153(9) .101(6) -.024(6) .003(5) .011(7) C12 .052(4) .063(4) .048(3) -.006(3) -.007(3) .003(3) C13 .074(5) .055(4) .075(4) -.002(4) .001(3) .011(3) C14 .094(6) .070(5) .074(5) .011(4) .011(4) -.011(4) C15 .089(6) .113(7) .053(4) .015(5) .001(3) -.011(5) C16 .119(7) .099(7) .057(4) .008(5) .001(4) .029(5) C17 .087(5) .057(5) .080(4) .012(4) -.001(3) .014(4) C18 .070(4) .111(7) .074(5) -.021(5) -.003(3) .013(5) C19 .094(7) .17(1) .091(5) -.022(6) -.033(6) -.001(7) C20 .081(6) .16(1) .108(7) .007(6) .001(5) -.019(7) C21 .102(8) .21(1) .19(1) -.060(7) -.017(7) .08(1) C22 .050(4) .055(5) .064(4) -.002(3) -.010(3) -.009(3) C23 .067(5) .064(5) .130(7) .003(4) -.037(5) -.005(5) C24 .149(9) .116(8) .19(1) .047(7) -.107(8) -.077(8) C25 .085(6) .080(6) .22(1) .012(5) -.062(6) .004(7) C26 .074(7) .24(2) .20(1) -.038(9) -.020(7) .05(1) N1 .055(3) .046(3) .067(3) -.007(3) -.016(2) .010(3) O1 .066(3) .084(4) .083(3) -.019(3) -.016(2) .019(3) O2 .094(4) .091(4) .089(3) -.014(3) -.022(3) .035(3) O3 .060(3) .052(3) .084(3) .002(2) -.022(2) -.001(2) O4 .110(5) .047(3) .164(6) -.027(3) -.056(4) .023(3) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.52(1) . . yes C1 O1 1.34(2) . . yes C1 O2 1.22(2) . . yes C2 C3 1.55(1) . . yes C2 C9 1.50(2) . . yes C3 C4 1.33(2) . . yes C3 C7 1.52(3) . . yes C4 C5 1.509(9) . . yes C4 C8 1.52(2) . . yes C5 C6 1.52(1) . . yes C5 N1 1.460(9) . . yes C6 C12 1.49(1) . . yes C9 C10 1.54(1) . . yes C9 C11 1.53(1) . . yes C12 C13 1.41(3) . . yes C12 C17 1.39(2) . . yes C13 C14 1.37(1) . . yes C14 C15 1.36(2) . . yes C15 C16 1.37(3) . . yes C16 C17 1.38(1) . . yes C18 C19 1.50(1) . . yes C18 C20 1.53(2) . . yes C18 C21 1.48(2) . . yes C18 O1 1.45(1) . . yes C22 N1 1.31(1) . . yes C22 O3 1.35(1) . . yes C22 O4 1.21(2) . . yes C23 C24 1.48(2) . . yes C23 C25 1.49(2) . . yes C23 C26 1.49(2) . . yes C23 O3 1.45(1) . . yes 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 O1 111(1) . . . yes C2 C1 O2 125(1) . . . yes O1 C1 O2 123.8(7) . . . yes C1 C2 C3 105.7(7) . . . yes C1 C2 C9 114(1) . . . yes C3 C2 C9 115(1) . . . yes C2 C3 C4 122(2) . . . yes C2 C3 C7 114(1) . . . yes C4 C3 C7 123.9(8) . . . yes C3 C4 C5 122(1) . . . yes C3 C4 C8 122.9(9) . . . yes C5 C4 C8 114.7(7) . . . yes C4 C5 C6 112.1(6) . . . yes C4 C5 N1 111.6(6) . . . yes C6 C5 N1 110.2(7) . . . yes C5 C6 C12 114.8(9) . . . yes C2 C9 C10 111(1) . . . yes C2 C9 C11 111(1) . . . yes C10 C9 C11 110.1(9) . . . yes C6 C12 C13 120(1) . . . yes C6 C12 C17 123(2) . . . yes C13 C12 C17 117(1) . . . yes C12 C13 C14 121(1) . . . yes C13 C14 C15 121(2) . . . yes C14 C15 C16 120(1) . . . yes C15 C16 C17 121(1) . . . yes C12 C17 C16 120(2) . . . yes C19 C18 C20 111(1) . . . yes C19 C18 C21 112(1) . . . yes C19 C18 O1 110.3(6) . . . yes C20 C18 C21 108.6(9) . . . yes C20 C18 O1 110(1) . . . yes C21 C18 O1 105(1) . . . yes N1 C22 O3 112(1) . . . yes N1 C22 O4 125(1) . . . yes O3 C22 O4 123.4(9) . . . yes C24 C23 C25 111(1) . . . yes C24 C23 C26 110(1) . . . yes C24 C23 O3 113.3(9) . . . yes C25 C23 C26 108(1) . . . yes C25 C23 O3 105(1) . . . yes C26 C23 O3 109.6(8) . . . yes C5 N1 C22 122(1) . . . yes C1 O1 C18 123(1) . . . yes C22 O3 C23 123(1) . . . yes 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 C1 C2 C3 C4 106(1) . . . . no C1 C2 C3 C7 -70(1) . . . . no C1 C2 C9 C10 -64(2) . . . . no C1 C2 C9 C11 173(1) . . . . no C2 C1 O1 C18 163.6(8) . . . . no C2 C3 C4 C5 -177.0(6) . . . . no C2 C3 C4 C8 -0.2(8) . . . . no C3 C2 C9 C10 174(1) . . . . no C3 C2 C9 C11 51(2) . . . . no C3 C4 C5 C6 109(1) . . . . no C3 C4 C5 N1 -126.3(8) . . . . no C4 C5 C6 C12 -173(1) . . . . no C4 C5 N1 C22 95(1) . . . . no C5 C6 C12 C13 72(1) . . . . no C5 C6 C12 C17 -108(1) . . . . no C6 C5 N1 C22 -139(1) . . . . no C6 C12 C13 C14 -178.1(7) . . . . no C6 C12 C17 C16 179.1(8) . . . . no C7 C3 C4 C5 -1(1) . . . . no C7 C3 C4 C8 175.7(7) . . . . no C8 C4 C5 C6 -68(1) . . . . no C8 C4 C5 N1 56.6(9) . . . . no C9 C2 C3 C4 -127(1) . . . . no C9 C2 C3 C7 56(1) . . . . no C12 C13 C14 C15 -1(1) . . . . no C13 C12 C17 C16 -1(1) . . . . no C13 C14 C15 C16 -1(1) . . . . no C14 C15 C16 C17 2(1) . . . . no C15 C16 C17 C12 -0(1) . . . . no C17 C12 C13 C14 2(1) . . . . no C19 C18 O1 C1 69(2) . . . . no C20 C18 O1 C1 -54(1) . . . . no C21 C18 O1 C1 -170.6(9) . . . . no C24 C23 O3 C22 61(1) . . . . no C25 C23 O3 C22 -177.8(8) . . . . no C26 C23 O3 C22 -62(2) . . . . no N1 C5 C6 C12 62(2) . . . . no N1 C22 O3 C23 174.4(7) . . . . no O1 C1 C2 C3 -78(2) . . . . no O1 C1 C2 C9 155(1) . . . . no O2 C1 C2 C3 98(1) . . . . no O2 C1 C2 C9 -29(2) . . . . no O2 C1 O1 C18 -13(1) . . . . no O3 C22 N1 C5 -176.4(6) . . . . no O4 C22 N1 C5 4(1) . . . . no O4 C22 O3 C23 -6(1) . . . . no