# Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2002 data_taj259 _database_code_CSD 183955 _journal_coden_Cambridge 182 loop_ _publ_author_name _publ_author_address 'Mark Ladlow' ; GlaxoSmithKline Cambridge Chemistry Unit Lensfield Road, Cambridge CB2 1EW UK ; 'Tajassus Aftab' ; School of Chemistry University of Leeds Leeds LS2 9JT UK ; 'Ronald Grigg' ; School of Chemistry University of Leeds Leeds LS2 9JT UK ; 'Visuvanathar Sridharan' ; School of Chemistry University of Leeds Leeds LS2 9JT UK ; 'Mark Thornton-Pett' ; School of Chemistry University of Leeds Leeds LS2 9JT UK ; # 1. SUBMISSION DETAILS _publ_contact_author_name 'Visuvanathar Sridharan' _publ_contact_author_address ; School of Chemistry University of Leeds Leeds LS2 9JT UK ; _publ_contact_author_phone '+44 (0)113 3436520' _publ_contact_author_fax '+44 (0)113 3436501' _publ_contact_author_email v.sridharan@chem.leeds.ac.uk _publ_requested_journal 'J. Chem Soc., Chem. Commun.' _publ_contact_letter ; The following set of data is supplementary data for compound 2e in the paper, details of which are given below ; #======================================================================= # 2. TITLE AND AUTHOR LIST _publ_section_title ; Novel synthesis of fused isoxazolidines via a palladium catalysed allene insertion-intramolecular 1,3-dipolar cycloaddition cascade reaction ; _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H19 N O3' _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 monoclinic _symmetry_space_group_name_H-M P21/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 12.6825(3) _cell_length_b 11.2067(2) _cell_length_c 11.1528(2) _cell_angle_alpha 90.00 _cell_angle_beta 106.9260(10) _cell_angle_gamma 90.00 _cell_volume 1516.47(5) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prism _exptl_crystal_colour 'pale yellow' _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.56 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.302 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 632 _exptl_absorpt_coefficient_mu 0.089 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9488 _exptl_absorpt_correction_T_max 0.9739 _exptl_absorpt_process_details ; Using multiple and symmetry-related data measurements via the program SORTAV See R.H. Blessing, Acta Cryst (1995), A51, 33-38 ; _exptl_special_details ; PLEASE NOTE cell_measurement_ fields are not relevant to area detector data, the entire data set is used to refine the cell, which is indexed from all observed reflections in a 15 degree phi range. ; _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 diffractometer' _diffrn_measurement_method ; Detector set at 30mm from sample with different 2theta offsets 1 degree phi exposures for chi=0 degree settings 1 degree omega exposures for chi=90 degree settings ; _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 24778 _diffrn_reflns_av_R_equivalents 0.0758 _diffrn_reflns_av_sigmaI/netI 0.0315 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 3.64 _diffrn_reflns_theta_max 25.99 _reflns_number_total 2950 _reflns_number_gt 2666 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement 'DENZO-SMN (Otwinowski & Minor, 1996)' _computing_data_reduction 'DENZO-SMN (Otwinowski & Minor, 1996)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ; ORTEP3 for Windows (Farrugia, 1997) XSeed (Barbour, 2001) ; _computing_publication_material 'WC (Thornton-Pett, 2000)' _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^)+(0.0543P)^2^+0.4031P] 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 SHELXL _refine_ls_extinction_coef 0.026(7) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 2950 _refine_ls_number_parameters 202 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0433 _refine_ls_R_factor_gt 0.0391 _refine_ls_wR_factor_ref 0.1080 _refine_ls_wR_factor_gt 0.1040 _refine_ls_goodness_of_fit_ref 1.029 _refine_ls_restrained_S_all 1.029 _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 O1 O 0.99776(7) 0.30639(9) 0.04558(8) 0.0408(3) Uani 1 1 d . . . N1 N 0.96867(9) 0.33224(10) 0.16165(10) 0.0345(3) Uani 1 1 d . . . C1 C 1.07049(11) 0.37516(14) 0.24952(13) 0.0422(3) Uani 1 1 d . . . H1A H 1.1259 0.3116 0.2661 0.063 Uiso 1 1 calc R . . H1B H 1.0564 0.3986 0.3281 0.063 Uiso 1 1 calc R . . H1C H 1.0977 0.4442 0.2134 0.063 Uiso 1 1 calc R . . C2 C 0.88533(10) 0.42708(11) 0.11520(11) 0.0294(3) Uani 1 1 d . . . H2 H 0.9204 0.4986 0.0890 0.035 Uiso 1 1 calc R . . C3 C 0.82744(10) 0.46235(10) 0.21035(11) 0.0294(3) Uani 1 1 d . . . C4 C 0.87341(10) 0.54484(11) 0.30513(11) 0.0336(3) Uani 1 1 d . . . H4 H 0.9433 0.5787 0.3106 0.040 Uiso 1 1 calc R . . C5 C 0.81926(12) 0.57829(12) 0.39121(12) 0.0382(3) Uani 1 1 d . . . H5 H 0.8525 0.6336 0.4557 0.046 Uiso 1 1 calc R . . C6 C 0.71615(12) 0.53069(12) 0.38282(12) 0.0385(3) Uani 1 1 d . . . H6 H 0.6793 0.5525 0.4425 0.046 Uiso 1 1 calc R . . C7 C 0.66726(11) 0.45167(11) 0.28765(12) 0.0351(3) Uani 1 1 d . . . H7 H 0.5961 0.4205 0.2807 0.042 Uiso 1 1 calc R . . C8 C 0.72258(10) 0.41789(10) 0.20213(11) 0.0291(3) Uani 1 1 d . . . O8 O 0.66704(7) 0.34163(7) 0.10856(8) 0.0320(2) Uani 1 1 d . . . C9 C 0.73508(10) 0.27992(11) 0.04633(11) 0.0320(3) Uani 1 1 d . . . H9A H 0.6875 0.2349 -0.0256 0.038 Uiso 1 1 calc R . . H9B H 0.7819 0.2217 0.1050 0.038 Uiso 1 1 calc R . . C10 C 0.80868(10) 0.36485(11) -0.00060(11) 0.0297(3) Uani 1 1 d . . . C11 C 0.89283(11) 0.28885(12) -0.04523(12) 0.0363(3) Uani 1 1 d . . . H11A H 0.8720 0.2035 -0.0501 0.044 Uiso 1 1 calc R . . H11B H 0.8952 0.3154 -0.1291 0.044 Uiso 1 1 calc R . . C12 C 0.73996(10) 0.44776(11) -0.10098(11) 0.0292(3) Uani 1 1 d . . . C13 C 0.73034(10) 0.56947(11) -0.08445(11) 0.0316(3) Uani 1 1 d . . . H13 H 0.7664 0.6040 -0.0053 0.038 Uiso 1 1 calc R . . C14 C 0.66914(10) 0.64245(11) -0.18101(11) 0.0326(3) Uani 1 1 d . . . H14 H 0.6633 0.7255 -0.1673 0.039 Uiso 1 1 calc R . . C15 C 0.61697(9) 0.59310(11) -0.29708(11) 0.0312(3) Uani 1 1 d . . . C16 C 0.62199(10) 0.47027(11) -0.31476(11) 0.0336(3) Uani 1 1 d . . . H16 H 0.5843 0.4354 -0.3932 0.040 Uiso 1 1 calc R . . C17 C 0.68225(10) 0.39977(11) -0.21730(11) 0.0327(3) Uani 1 1 d . . . H17 H 0.6846 0.3160 -0.2297 0.039 Uiso 1 1 calc R . . O15 O 0.55835(7) 0.65763(8) -0.39963(8) 0.0384(3) Uani 1 1 d . . . C18 C 0.56516(12) 0.78470(12) -0.38861(13) 0.0419(3) Uani 1 1 d . . . H18A H 0.5288 0.8112 -0.3269 0.063 Uiso 1 1 calc R . . H18B H 0.5287 0.8210 -0.4701 0.063 Uiso 1 1 calc R . . H18C H 0.6427 0.8090 -0.3613 0.063 Uiso 1 1 calc R . . 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 0.0333(5) 0.0543(6) 0.0354(5) -0.0032(4) 0.0109(4) 0.0086(4) N1 0.0302(6) 0.0423(6) 0.0304(5) 0.0009(4) 0.0080(4) 0.0058(4) C1 0.0292(7) 0.0553(8) 0.0382(7) 0.0003(6) 0.0035(5) 0.0043(6) C2 0.0274(6) 0.0315(6) 0.0285(6) 0.0026(5) 0.0067(5) 0.0003(5) C3 0.0301(6) 0.0302(6) 0.0267(6) 0.0032(4) 0.0064(5) 0.0014(5) C4 0.0324(6) 0.0346(7) 0.0302(6) 0.0011(5) 0.0036(5) -0.0004(5) C5 0.0469(8) 0.0361(7) 0.0287(6) -0.0014(5) 0.0063(5) 0.0019(6) C6 0.0498(8) 0.0361(7) 0.0334(7) 0.0029(5) 0.0182(6) 0.0070(6) C7 0.0352(7) 0.0344(7) 0.0381(7) 0.0056(5) 0.0147(5) 0.0025(5) C8 0.0300(6) 0.0283(6) 0.0274(6) 0.0033(5) 0.0058(5) 0.0012(5) O8 0.0294(5) 0.0346(5) 0.0315(5) -0.0013(3) 0.0078(4) -0.0034(3) C9 0.0347(6) 0.0300(6) 0.0301(6) -0.0013(5) 0.0077(5) -0.0008(5) C10 0.0310(6) 0.0306(6) 0.0274(6) -0.0003(5) 0.0081(5) 0.0010(5) C11 0.0362(7) 0.0389(7) 0.0324(6) -0.0016(5) 0.0079(5) 0.0059(5) C12 0.0285(6) 0.0331(6) 0.0269(6) 0.0004(5) 0.0092(5) -0.0008(5) C13 0.0317(6) 0.0342(6) 0.0273(6) -0.0024(5) 0.0060(5) -0.0017(5) C14 0.0325(6) 0.0313(6) 0.0327(6) -0.0010(5) 0.0076(5) -0.0001(5) C15 0.0259(6) 0.0386(7) 0.0280(6) 0.0032(5) 0.0060(5) 0.0002(5) C16 0.0347(7) 0.0379(7) 0.0263(6) -0.0043(5) 0.0060(5) -0.0024(5) C17 0.0362(7) 0.0315(6) 0.0307(6) -0.0029(5) 0.0101(5) -0.0008(5) O15 0.0374(5) 0.0405(5) 0.0313(5) 0.0037(4) 0.0004(4) 0.0013(4) C18 0.0379(7) 0.0398(7) 0.0421(7) 0.0090(6) 0.0023(6) 0.0025(6) _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 C11 1.4319(16) . ? O1 N1 1.4743(14) . ? N1 C1 1.4569(17) . ? N1 C2 1.4820(16) . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? C2 C3 1.5083(16) . ? C2 C10 1.5389(16) . ? C2 H2 1.0000 . ? C3 C4 1.3975(17) . ? C3 C8 1.3980(17) . ? C4 C5 1.3847(18) . ? C4 H4 0.9500 . ? C5 C6 1.390(2) . ? C5 H5 0.9500 . ? C6 C7 1.3827(19) . ? C6 H6 0.9500 . ? C7 C8 1.3910(17) . ? C7 H7 0.9500 . ? C8 O8 1.3739(14) . ? O8 C9 1.4330(15) . ? C9 C10 1.5283(17) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 C12 1.5192(16) . ? C10 C11 1.5562(17) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 C13 1.3865(17) . ? C12 C17 1.3983(16) . ? C13 C14 1.3944(17) . ? C13 H13 0.9500 . ? C14 C15 1.3858(17) . ? C14 H14 0.9500 . ? C15 O15 1.3743(14) . ? C15 C16 1.3947(18) . ? C16 C17 1.3806(17) . ? C16 H16 0.9500 . ? C17 H17 0.9500 . ? O15 C18 1.4298(16) . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 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 C11 O1 N1 103.27(9) . . ? C1 N1 O1 104.84(9) . . ? C1 N1 C2 113.62(11) . . ? O1 N1 C2 99.75(9) . . ? N1 C1 H1A 109.5 . . ? N1 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? N1 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? N1 C2 C3 112.69(9) . . ? N1 C2 C10 100.39(9) . . ? C3 C2 C10 113.03(10) . . ? N1 C2 H2 110.1 . . ? C3 C2 H2 110.1 . . ? C10 C2 H2 110.1 . . ? C4 C3 C8 117.69(11) . . ? C4 C3 C2 121.62(11) . . ? C8 C3 C2 120.60(11) . . ? C5 C4 C3 121.44(12) . . ? C5 C4 H4 119.3 . . ? C3 C4 H4 119.3 . . ? C4 C5 C6 119.75(12) . . ? C4 C5 H5 120.1 . . ? C6 C5 H5 120.1 . . ? C7 C6 C5 120.02(12) . . ? C7 C6 H6 120.0 . . ? C5 C6 H6 120.0 . . ? C6 C7 C8 119.84(12) . . ? C6 C7 H7 120.1 . . ? C8 C7 H7 120.1 . . ? O8 C8 C7 116.15(10) . . ? O8 C8 C3 122.62(10) . . ? C7 C8 C3 121.21(11) . . ? C8 O8 C9 114.85(9) . . ? O8 C9 C10 112.29(10) . . ? O8 C9 H9A 109.1 . . ? C10 C9 H9A 109.1 . . ? O8 C9 H9B 109.1 . . ? C10 C9 H9B 109.1 . . ? H9A C9 H9B 107.9 . . ? C12 C10 C9 110.90(10) . . ? C12 C10 C2 115.34(10) . . ? C9 C10 C2 107.12(9) . . ? C12 C10 C11 113.50(10) . . ? C9 C10 C11 108.23(10) . . ? C2 C10 C11 101.07(9) . . ? O1 C11 C10 106.33(9) . . ? O1 C11 H11A 110.5 . . ? C10 C11 H11A 110.5 . . ? O1 C11 H11B 110.5 . . ? C10 C11 H11B 110.5 . . ? H11A C11 H11B 108.7 . . ? C13 C12 C17 117.34(11) . . ? C13 C12 C10 123.88(11) . . ? C17 C12 C10 118.78(10) . . ? C12 C13 C14 121.67(11) . . ? C12 C13 H13 119.2 . . ? C14 C13 H13 119.2 . . ? C15 C14 C13 119.63(11) . . ? C15 C14 H14 120.2 . . ? C13 C14 H14 120.2 . . ? O15 C15 C14 124.25(11) . . ? O15 C15 C16 115.95(10) . . ? C14 C15 C16 119.80(11) . . ? C17 C16 C15 119.42(11) . . ? C17 C16 H16 120.3 . . ? C15 C16 H16 120.3 . . ? C16 C17 C12 122.04(11) . . ? C16 C17 H17 119.0 . . ? C12 C17 H17 119.0 . . ? C15 O15 C18 116.62(10) . . ? O15 C18 H18A 109.5 . . ? O15 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? O15 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 25.99 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.245 _refine_diff_density_min -0.173 _refine_diff_density_rms 0.036