#------------------------------------------------------------------------------
#$Date: 2016-03-26 15:08:31 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180289 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/03/7150371.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7150371
loop_
_publ_author_name
'Griesbeck, Axel G.'
'Bondock, Samir'
'Lex, Johann'
_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.
;
_journal_issue                   8
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              1113
_journal_page_last               1115
_journal_paper_doi               10.1039/b401990c
_journal_volume                  2
_journal_year                    2004
_chemical_formula_sum            'C11 H19 N O6'
_chemical_formula_weight         261.27
_chemical_name_systematic
;
?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 108.02(1)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.319(1)
_cell_length_b                   21.573(1)
_cell_length_c                   8.799(1)
_cell_measurement_reflns_used    2722
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.54
_cell_measurement_theta_min      1.89
_cell_volume                     1321.2(3)
_computing_cell_refinement       'Nonius DENZO'
_computing_data_collection       'Nonius COLLECT'
_computing_data_reduction        'Nonius DENZO'
_computing_molecular_graphics    SCHAKAL
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.891
_diffrn_measured_fraction_theta_max 0.891
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       Phi/Omega-scans
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0923
_diffrn_reflns_av_sigmaI/netI    0.1314
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            5302
_diffrn_reflns_theta_full        27.54
_diffrn_reflns_theta_max         27.54
_diffrn_reflns_theta_min         1.89
_exptl_absorpt_coefficient_mu    0.107
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.314
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             560
_exptl_crystal_size_max          .20
_exptl_crystal_size_mid          .08
_exptl_crystal_size_min          .08
_refine_diff_density_max         0.153
_refine_diff_density_min         -0.232
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.956
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         2722
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.956
_refine_ls_R_factor_all          0.1965
_refine_ls_R_factor_gt           0.0562
_refine_ls_shift/su_max          0.009
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0535P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1017
_refine_ls_wR_factor_ref         0.1390
_reflns_number_gt                1023
_reflns_number_total             2722
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b401990c.txt
_cod_data_source_block           4b
_cod_original_cell_volume        1321.2(2)
_cod_original_sg_symbol_H-M      P21/c
_cod_database_code               7150371
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'
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_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'
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) . . ?
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) . ?
