# Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2004 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_Cambridge 0177 _publ_contact_author_name 'ProfD Axel G Griesbeck' _publ_contact_author_address ; Organic Chemistry University of Cologne Greinstr. 4 Koln D-50939 ; _publ_contact_author_email GRIESBECK@UNI-KOELN.DE _publ_section_title ; Stereoselective generation of vicinal stereogenic quaternary centers by photocycloaddition of 5-methoxy oxazoles to alpha-keto esters: synthesis of erythro beta-hydroxy dimethyl aspartates ; loop_ _publ_author_name 'Axel G. Griesbeck' 'Samir Bondock' 'Johann Lex' data_4b _database_code_depnum_ccdc_archive 'CCDC 231106' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C11 H19 N O6' _chemical_formula_weight 261.27 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 7.319(1) _cell_length_b 21.573(1) _cell_length_c 8.799(1) _cell_angle_alpha 90.00 _cell_angle_beta 108.02(1) _cell_angle_gamma 90.00 _cell_volume 1321.2(2) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 2722 _cell_measurement_theta_min 1.89 _cell_measurement_theta_max 27.54 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max .20 _exptl_crystal_size_mid .08 _exptl_crystal_size_min .08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.314 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 560 _exptl_absorpt_coefficient_mu 0.107 _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 293(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' _diffrn_measurement_method Phi/Omega-scans _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5302 _diffrn_reflns_av_R_equivalents 0.0923 _diffrn_reflns_av_sigmaI/netI 0.1314 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -27 _diffrn_reflns_limit_k_max 27 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 1.89 _diffrn_reflns_theta_max 27.54 _reflns_number_total 2722 _reflns_number_gt 1023 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Nonius COLLECT' _computing_cell_refinement 'Nonius DENZO' _computing_data_reduction 'Nonius DENZO' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics SCHAKAL _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0535P)^2^+0.0000P] 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 2722 _refine_ls_number_parameters 218 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1965 _refine_ls_R_factor_gt 0.0562 _refine_ls_wR_factor_ref 0.1390 _refine_ls_wR_factor_gt 0.1017 _refine_ls_goodness_of_fit_ref 0.956 _refine_ls_restrained_S_all 0.956 _refine_ls_shift/su_max 0.009 _refine_ls_shift/su_mean 0.001 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 0.9642(8) 0.2536(3) 0.7936(8) 0.0864(15) Uani 1 1 d . . . C2 C 0.8478(4) 0.35248(18) 0.8263(5) 0.0516(10) Uani 1 1 d . . . C3 C 0.7235(3) 0.40867(15) 0.7470(4) 0.0411(8) Uani 1 1 d . . . C4 C 0.5090(4) 0.39574(15) 0.7421(4) 0.0423(9) Uani 1 1 d . . . C5 C 0.4413(4) 0.33272(18) 0.6630(5) 0.0509(10) Uani 1 1 d . . . C6 C 0.4399(6) 0.22475(19) 0.7011(5) 0.0889(14) Uani 1 1 d . . . H6A H 0.3044 0.2206 0.6485 0.147(8) Uiso 1 1 calc R . . H6B H 0.4804 0.1944 0.7846 0.147(8) Uiso 1 1 calc R . . H6C H 0.5080 0.2185 0.6250 0.147(8) Uiso 1 1 calc R . . C7 C 0.8098(5) 0.46663(17) 0.8445(5) 0.0497(9) Uani 1 1 d . . . C8 C 0.7206(5) 0.5284(2) 0.7820(5) 0.0574(11) Uani 1 1 d . . . C9 C 0.8784(4) 0.41625(14) 0.5350(4) 0.0482(9) Uani 1 1 d . . . C10 C 0.8490(4) 0.42164(16) 0.3593(4) 0.0627(11) Uani 1 1 d . . . H10A H 0.8909 0.4618 0.3364 0.147(8) Uiso 1 1 calc R . . H10B H 0.7152 0.4165 0.3017 0.147(8) Uiso 1 1 calc R . . H10C H 0.9221 0.3901 0.3272 0.147(8) Uiso 1 1 calc R . . C11 C 0.4829(6) 0.3996(2) 0.9072(5) 0.0568(11) Uani 1 1 d . . . N1 N 0.7196(4) 0.41410(12) 0.5813(3) 0.0434(7) Uani 1 1 d . . . O1 O 0.8477(3) 0.30753(12) 0.7229(3) 0.0571(7) Uani 1 1 d . . . O2 O 0.9313(3) 0.35010(12) 0.9669(3) 0.0743(8) Uani 1 1 d . . . O3 O 0.3991(3) 0.44229(11) 0.6401(3) 0.0517(7) Uani 1 1 d . . . O4 O 0.3633(3) 0.32602(12) 0.5230(3) 0.0731(8) Uani 1 1 d . . . O5 O 0.4805(3) 0.28632(12) 0.7691(3) 0.0616(7) Uani 1 1 d . . . O6 O 1.0386(3) 0.41378(11) 0.6349(3) 0.0659(8) Uani 1 1 d . . . H1A H 1.106(8) 0.273(3) 0.838(7) 0.18(2) Uiso 1 1 d . . . H1B H 0.939(5) 0.226(2) 0.702(5) 0.101(16) Uiso 1 1 d . . . H1C H 0.913(6) 0.235(2) 0.880(6) 0.13(2) Uiso 1 1 d . . . H7A H 0.950(4) 0.4660(13) 0.851(3) 0.058(9) Uiso 1 1 d . . . H7B H 0.808(4) 0.4576(13) 0.955(4) 0.050(10) Uiso 1 1 d . . . H8A H 0.793(4) 0.5634(17) 0.834(4) 0.079(12) Uiso 1 1 d . . . H8B H 0.712(4) 0.5351(16) 0.658(5) 0.083(12) Uiso 1 1 d . . . H8C H 0.578(5) 0.5313(14) 0.786(3) 0.074(10) Uiso 1 1 d . . . H11A H 0.497(5) 0.4439(18) 0.944(4) 0.099(14) Uiso 1 1 d . . . H11B H 0.580(5) 0.3714(17) 0.983(4) 0.077(12) Uiso 1 1 d . . . H11C H 0.355(4) 0.3869(13) 0.900(3) 0.060(10) Uiso 1 1 d . . . H1N H 0.612(4) 0.4188(14) 0.511(3) 0.045(9) Uiso 1 1 d . . . H3O H 0.284(5) 0.4341(18) 0.625(4) 0.089(14) 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 0.103(4) 0.060(4) 0.093(5) 0.008(3) 0.025(3) 0.032(3) C2 0.0388(19) 0.054(3) 0.058(3) -0.003(2) 0.0093(18) -0.0014(17) C3 0.0309(15) 0.055(2) 0.036(2) -0.0026(18) 0.0082(13) -0.0004(15) C4 0.0354(17) 0.051(2) 0.041(2) 0.0022(18) 0.0124(15) -0.0006(15) C5 0.042(2) 0.067(3) 0.049(3) -0.005(2) 0.0213(18) -0.0058(18) C6 0.128(3) 0.049(3) 0.109(4) -0.021(3) 0.066(3) -0.020(2) C7 0.042(2) 0.057(3) 0.048(3) -0.001(2) 0.0099(17) -0.0017(17) C8 0.051(2) 0.059(3) 0.060(3) -0.007(2) 0.0134(19) -0.006(2) C9 0.037(2) 0.045(2) 0.066(3) -0.0001(19) 0.0221(18) -0.0016(15) C10 0.064(2) 0.073(3) 0.066(3) 0.000(2) 0.0406(19) -0.0041(18) C11 0.056(2) 0.066(3) 0.055(3) -0.008(2) 0.027(2) -0.008(2) N1 0.0242(14) 0.062(2) 0.0441(19) -0.0008(15) 0.0103(13) -0.0004(13) O1 0.0539(13) 0.0528(18) 0.0648(19) -0.0015(15) 0.0187(12) 0.0082(12) O2 0.0742(16) 0.074(2) 0.0564(19) 0.0035(16) -0.0070(14) 0.0137(13) O3 0.0303(12) 0.0643(18) 0.0611(17) 0.0103(13) 0.0151(11) 0.0027(11) O4 0.0748(16) 0.086(2) 0.0523(18) -0.0168(16) 0.0114(13) -0.0137(14) O5 0.0807(16) 0.0492(18) 0.0624(19) -0.0033(15) 0.0333(14) -0.0103(13) O6 0.0299(12) 0.090(2) 0.0785(18) 0.0064(15) 0.0181(11) 0.0000(11) _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 1.463(5) . ? C2 O2 1.199(4) . ? C2 O1 1.330(4) . ? C2 C3 1.546(5) . ? C3 N1 1.454(4) . ? C3 C7 1.537(4) . ? C3 C4 1.582(4) . ? C4 O3 1.420(3) . ? C4 C11 1.525(4) . ? C4 C5 1.538(5) . ? C5 O4 1.196(4) . ? C5 O5 1.338(4) . ? C6 O5 1.449(4) . ? C7 C8 1.510(5) . ? C9 O6 1.230(3) . ? C9 N1 1.346(4) . ? C9 C10 1.498(4) . ? 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 O2 C2 O1 124.5(3) . . ? O2 C2 C3 122.7(4) . . ? O1 C2 C3 112.8(3) . . ? N1 C3 C2 110.0(3) . . ? N1 C3 C7 111.8(3) . . ? C2 C3 C7 107.7(3) . . ? N1 C3 C4 106.0(2) . . ? C2 C3 C4 108.3(3) . . ? C7 C3 C4 113.0(3) . . ? O3 C4 C11 110.5(3) . . ? O3 C4 C5 107.4(3) . . ? C11 C4 C5 111.2(3) . . ? O3 C4 C3 104.8(2) . . ? C11 C4 C3 112.3(3) . . ? C5 C4 C3 110.3(2) . . ? O4 C5 O5 124.0(4) . . ? O4 C5 C4 123.9(4) . . ? O5 C5 C4 112.1(3) . . ? C8 C7 C3 117.3(3) . . ? O6 C9 N1 120.3(3) . . ? O6 C9 C10 122.8(3) . . ? N1 C9 C10 116.9(3) . . ? C9 N1 C3 123.7(3) . . ? C2 O1 C1 114.4(3) . . ? C5 O5 C6 115.2(3) . . ? _diffrn_measured_fraction_theta_max 0.891 _diffrn_reflns_theta_full 27.54 _diffrn_measured_fraction_theta_full 0.891 _refine_diff_density_max 0.153 _refine_diff_density_min -0.232 _refine_diff_density_rms 0.044