# 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 F² against ALL reflections.  The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement.  R-factors based
on F² 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/[σ²(Fo²)+(0.0535P)²+0.0000P] where P=(Fo²+2Fc²)/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


