##############################################################################
###                                                                        ###
###        Electronic paper (Acta Crystallographica Section E)             ###
###                                                                        ###
##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in Acta     #
# Crystallographica Section E. It conforms to the requirements of Notes      #
# for Authors for Section E, and has been peer reviewed under the auspices   #
# of the IUCr Commission on Journals.                                        #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic. The current version number is 2.4.    #
#                                                                            #
# Software is freely available for graphical display of the structure(s) in  #
# this CIF.  For information consult the CIF home page http://www.iucr.org/  #
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data_I
_audit_creation_method     SHELXL97
_chemical_name_systematic
;
(4S)-Benzyl 4-isopropyl-5-oxo-1,3-oxazolidine-3-carboxylate
;
_chemical_name_common     ?
_chemical_formula_moiety     'C14 H17 N O4'
_chemical_formula_sum     'C14 H17 N O4'
_chemical_formula_iupac     'C14 H17 N O4'
_chemical_formula_weight     263.29
_chemical_melting_point     ?
_symmetry_cell_setting     orthorhombic
_symmetry_space_group_name_H-M     'P 21 21 21'
_symmetry_space_group_name_Hall     'P 2ac 2ab'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x+1/2, -y, z+1/2'
    '-x, y+1/2, -z+1/2'
    'x+1/2, -y+1/2, -z'
_cell_length_a     6.0528(2)
_cell_length_b     13.1581(5)
_cell_length_c     16.6778(6)
_cell_angle_alpha     90.00
_cell_angle_beta     90.00
_cell_angle_gamma     90.00
_cell_volume     1328.28(8)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     2839
_cell_measurement_theta_min     2.8843
_cell_measurement_theta_max     32.5952
_cell_measurement_temperature     153(2)
_exptl_crystal_description     needle
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.50
_exptl_crystal_size_mid     0.17
_exptl_crystal_size_min     0.09
_exptl_crystal_density_diffrn     1.317
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     560
_exptl_absorpt_coefficient_mu     0.097
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Bruker, 2001)'
_exptl_absorpt_correction_T_min     0.953
_exptl_absorpt_correction_T_max     0.991
_exptl_special_details
;
;
_diffrn_ambient_temperature     153(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Bruker APEX CCD'
_diffrn_measurement_method     'φ and ω'
_diffrn_detector_area_resol_mean     16.1903
_diffrn_reflns_number     5718
_diffrn_reflns_av_R_equivalents     0.0276
_diffrn_reflns_av_sigmaI/netI     0.0279
_diffrn_reflns_theta_min     2.89
_diffrn_reflns_theta_max     25.00
_diffrn_reflns_theta_full     25.00
_diffrn_measured_fraction_theta_max     0.992
_diffrn_measured_fraction_theta_full     0.992
_diffrn_reflns_limit_h_min     -7
_diffrn_reflns_limit_h_max     7
_diffrn_reflns_limit_k_min     -14
_diffrn_reflns_limit_k_max     15
_diffrn_reflns_limit_l_min     -19
_diffrn_reflns_limit_l_max     19
_diffrn_standards_number     0
_diffrn_standards_interval_count     0
_diffrn_standards_interval_time     0
_diffrn_standards_decay_%     0
_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.
;
_reflns_number_total     1368
_reflns_number_gt     1100
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0367
_refine_ls_R_factor_gt     0.0278
_refine_ls_wR_factor_gt     0.0596
_refine_ls_wR_factor_ref     0.0620
_refine_ls_goodness_of_fit_ref     0.988
_refine_ls_restrained_S_all     0.988
_refine_ls_number_reflns     1368
_refine_ls_number_parameters     172
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
               'calc w = 1/[σ²(Fo²)+(0.0398P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.124
_refine_diff_density_min     -0.131
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
_refine_ls_abs_structure_details     ?
_refine_ls_abs_structure_Flack     ?
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 0.0000
                         '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 0.0000
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'O' 'O' 0.0106 0.0000
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'SMART (Bruker, 2001)'
_computing_cell_refinement     'SAINT (Bruker, 2001)'
_computing_data_reduction     'SAINT (Bruker, 2001)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics     'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material     'SHELXL97 (Sheldrick, 2008)'
loop_
    _atom_site_type_symbol
    _atom_site_label
    _atom_site_fract_x
    _atom_site_fract_y
    _atom_site_fract_z
    _atom_site_U_iso_or_equiv
    _atom_site_adp_type
    _atom_site_calc_flag
    _atom_site_refinement_flags
    _atom_site_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    O O1 -0.4445(2) -0.27913(11) 0.18553(8) 0.0312(3) Uani d . 1 . .
    C C2 -0.6151(3) -0.24832(15) 0.13165(12) 0.0315(5) Uani d . 1 . .
    H H2A -0.7493 -0.2318 0.1607 0.038 Uiso calc R 1 . .
    H H2B -0.6473 -0.3017 0.0932 0.038 Uiso calc R 1 . .
    N N3 -0.5269(3) -0.15900(11) 0.09160(9) 0.0250(4) Uani d . 1 . .
    C C4 -0.3046(3) -0.13532(13) 0.11905(11) 0.0242(4) Uani d . 1 . .
    H H4A -0.2008 -0.1412 0.0742 0.029 Uiso calc R 1 . .
    O O5 -0.1002(2) -0.23774(11) 0.21593(8) 0.0361(4) Uani d . 1 . .
    C C5 -0.2637(3) -0.22044(15) 0.17824(11) 0.0261(4) Uani d . 1 . .
    O O6 -0.7800(2) -0.17466(10) -0.00699(9) 0.0348(4) Uani d . 1 . .
    C C6 -0.6135(3) -0.13483(15) 0.01957(12) 0.0268(5) Uani d . 1 . .
    O O7 -0.4976(2) -0.06146(10) -0.01706(7) 0.0308(3) Uani d . 1 . .
    C C8 -0.5807(4) -0.02766(16) -0.09484(11) 0.0325(5) Uani d . 1 . .
    H H8A -0.6570 -0.0837 -0.1206 0.039 Uiso calc R 1 . .
    H H8B -0.4566 -0.0089 -0.1286 0.039 Uiso calc R 1 . .
    C C9 -0.7346(4) 0.06079(15) -0.08858(11) 0.0287(5) Uani d . 1 . .
    C C10 -0.9408(4) 0.05173(17) -0.05121(12) 0.0361(5) Uani d . 1 . .
    H H10A -0.9819 -0.0099 -0.0283 0.043 Uiso calc R 1 . .
    C C11 -1.0833(4) 0.13326(18) -0.04812(13) 0.0435(6) Uani d . 1 . .
    H H11A -1.2181 0.1269 -0.0218 0.052 Uiso calc R 1 . .
    C C12 -1.0276(4) 0.22421(19) -0.08374(14) 0.0482(6) Uani d . 1 . .
    H H12A -1.1247 0.2790 -0.0821 0.058 Uiso calc R 1 . .
    C C13 -0.8260(4) 0.23316(17) -0.12188(15) 0.0467(6) Uani d . 1 . .
    H H13A -0.7882 0.2941 -0.1466 0.056 Uiso calc R 1 . .
    C C14 -0.6801(4) 0.15252(15) -0.12363(12) 0.0365(5) Uani d . 1 . .
    H H14A -0.5438 0.1600 -0.1487 0.044 Uiso calc R 1 . .
    C C15 -0.2829(3) -0.02961(14) 0.15749(11) 0.0266(5) Uani d . 1 . .
    H H15A -0.3376 0.0202 0.1186 0.032 Uiso calc R 1 . .
    C C16 -0.4247(4) -0.02032(17) 0.23247(13) 0.0378(5) Uani d . 1 . .
    H H16A -0.4075 0.0464 0.2550 0.057 Uiso calc R 1 . .
    H H16B -0.3791 -0.0703 0.2710 0.057 Uiso calc R 1 . .
    H H16C -0.5769 -0.0312 0.2187 0.057 Uiso calc R 1 . .
    C C17 -0.0424(3) -0.00377(16) 0.17484(13) 0.0375(5) Uani d . 1 . .
    H H17A -0.0338 0.0625 0.1988 0.056 Uiso calc R 1 . .
    H H17B 0.0401 -0.0043 0.1257 0.056 Uiso calc R 1 . .
    H H17C 0.0182 -0.0532 0.2110 0.056 Uiso calc R 1 . .
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
    O1 0.0307(8) 0.0288(7) 0.0341(7) -0.0021(7) 0.0004(6) 0.0064(6)
    C2 0.0256(11) 0.0325(12) 0.0363(11) -0.0034(10) 0.0005(9) 0.0050(10)
    N3 0.0244(9) 0.0243(8) 0.0261(9) -0.0028(7) -0.0006(7) 0.0013(7)
    C4 0.0224(10) 0.0257(10) 0.0244(10) -0.0005(9) 0.0020(8) 0.0008(9)
    O5 0.0331(8) 0.0374(8) 0.0378(8) 0.0059(7) -0.0048(7) 0.0036(7)
    C5 0.0274(11) 0.0248(10) 0.0261(10) 0.0032(9) 0.0033(10) -0.0028(9)
    O6 0.0328(8) 0.0344(8) 0.0372(8) -0.0060(7) -0.0088(7) -0.0012(7)
    C6 0.0267(11) 0.0232(11) 0.0304(11) 0.0002(10) 0.0014(9) -0.0039(9)
    O7 0.0325(8) 0.0313(7) 0.0286(7) -0.0057(7) -0.0029(6) 0.0055(6)
    C8 0.0396(12) 0.0346(11) 0.0232(10) -0.0033(10) -0.0023(9) 0.0027(9)
    C9 0.0375(12) 0.0298(11) 0.0187(9) -0.0039(10) -0.0045(9) 0.0003(9)
    C10 0.0414(13) 0.0358(12) 0.0310(11) -0.0023(11) 0.0010(10) 0.0037(10)
    C11 0.0388(13) 0.0509(15) 0.0408(13) 0.0027(13) -0.0022(11) -0.0038(12)
    C12 0.0554(17) 0.0377(14) 0.0514(14) 0.0107(13) -0.0094(13) -0.0075(12)
    C13 0.0624(16) 0.0283(12) 0.0493(13) -0.0039(12) -0.0102(13) 0.0045(12)
    C14 0.0430(13) 0.0360(12) 0.0305(11) -0.0070(11) -0.0022(10) 0.0017(11)
    C15 0.0299(11) 0.0212(10) 0.0288(10) 0.0002(9) -0.0049(9) 0.0012(8)
    C16 0.0353(12) 0.0364(12) 0.0419(12) 0.0045(10) 0.0002(10) -0.0116(10)
    C17 0.0365(13) 0.0365(13) 0.0395(12) -0.0090(11) -0.0019(10) -0.0004(10)
_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_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    O1 C5 . 1.345(2) ?
    O1 C2 . 1.428(2) ?
    C2 N3 . 1.454(2) ?
    C2 H2A . 0.970 ?
    C2 H2B . 0.970 ?
    N3 C6 . 1.349(2) ?
    N3 C4 . 1.455(2) ?
    C4 C5 . 1.513(3) ?
    C4 C15 . 1.537(2) ?
    C4 H4A . 0.980 ?
    O5 C5 . 1.194(2) ?
    O6 C6 . 1.219(2) ?
    C6 O7 . 1.340(2) ?
    O7 C8 . 1.461(2) ?
    C8 C9 . 1.495(3) ?
    C8 H8A . 0.970 ?
    C8 H8B . 0.970 ?
    C9 C14 . 1.381(3) ?
    C9 C10 . 1.400(3) ?
    C10 C11 . 1.378(3) ?
    C10 H10A . 0.930 ?
    C11 C12 . 1.378(4) ?
    C11 H11A . 0.930 ?
    C12 C13 . 1.381(4) ?
    C12 H12A . 0.930 ?
    C13 C14 . 1.381(3) ?
    C13 H13A . 0.930 ?
    C14 H14A . 0.930 ?
    C15 C16 . 1.522(3) ?
    C15 C17 . 1.523(3) ?
    C15 H15A . 0.980 ?
    C16 H16A . 0.960 ?
    C16 H16B . 0.960 ?
    C16 H16C . 0.960 ?
    C17 H17A . 0.960 ?
    C17 H17B . 0.960 ?
    C17 H17C . 0.960 ?
loop_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    C5 O1 C2 . . 111.63(15) ?
    O1 C2 N3 . . 104.66(15) ?
    O1 C2 H2A . . 110.8 ?
    N3 C2 H2A . . 110.8 ?
    O1 C2 H2B . . 110.8 ?
    N3 C2 H2B . . 110.8 ?
    H2A C2 H2B . . 108.9 ?
    C6 N3 C2 . . 117.21(16) ?
    C6 N3 C4 . . 126.09(16) ?
    C2 N3 C4 . . 111.61(15) ?
    N3 C4 C5 . . 101.42(15) ?
    N3 C4 C15 . . 113.81(15) ?
    C5 C4 C15 . . 112.56(15) ?
    N3 C4 H4A . . 109.6 ?
    C5 C4 H4A . . 109.6 ?
    C15 C4 H4A . . 109.6 ?
    O5 C5 O1 . . 121.14(18) ?
    O5 C5 C4 . . 128.30(19) ?
    O1 C5 C4 . . 110.55(16) ?
    O6 C6 O7 . . 125.19(18) ?
    O6 C6 N3 . . 122.92(18) ?
    O7 C6 N3 . . 111.88(17) ?
    C6 O7 C8 . . 116.37(15) ?
    O7 C8 C9 . . 112.93(16) ?
    O7 C8 H8A . . 109.0 ?
    C9 C8 H8A . . 109.0 ?
    O7 C8 H8B . . 109.0 ?
    C9 C8 H8B . . 109.0 ?
    H8A C8 H8B . . 107.8 ?
    C14 C9 C10 . . 118.4(2) ?
    C14 C9 C8 . . 120.14(19) ?
    C10 C9 C8 . . 121.37(18) ?
    C11 C10 C9 . . 120.6(2) ?
    C11 C10 H10A . . 119.7 ?
    C9 C10 H10A . . 119.7 ?
    C10 C11 C12 . . 120.5(2) ?
    C10 C11 H11A . . 119.8 ?
    C12 C11 H11A . . 119.8 ?
    C11 C12 C13 . . 119.3(2) ?
    C11 C12 H12A . . 120.4 ?
    C13 C12 H12A . . 120.4 ?
    C14 C13 C12 . . 120.6(2) ?
    C14 C13 H13A . . 119.7 ?
    C12 C13 H13A . . 119.7 ?
    C13 C14 C9 . . 120.7(2) ?
    C13 C14 H14A . . 119.7 ?
    C9 C14 H14A . . 119.7 ?
    C16 C15 C17 . . 111.42(17) ?
    C16 C15 C4 . . 111.55(16) ?
    C17 C15 C4 . . 111.28(16) ?
    C16 C15 H15A . . 107.4 ?
    C17 C15 H15A . . 107.4 ?
    C4 C15 H15A . . 107.4 ?
    C15 C16 H16A . . 109.5 ?
    C15 C16 H16B . . 109.5 ?
    H16A C16 H16B . . 109.5 ?
    C15 C16 H16C . . 109.5 ?
    H16A C16 H16C . . 109.5 ?
    H16B C16 H16C . . 109.5 ?
    C15 C17 H17A . . 109.5 ?
    C15 C17 H17B . . 109.5 ?
    H17A C17 H17B . . 109.5 ?
    C15 C17 H17C . . 109.5 ?
    H17A C17 H17C . . 109.5 ?
    H17B C17 H17C . . 109.5 ?
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_site_symmetry_1
    _geom_torsion_site_symmetry_2
    _geom_torsion_site_symmetry_3
    _geom_torsion_site_symmetry_4
    _geom_torsion
    _geom_torsion_publ_flag
    C5 O1 C2 N3 . . . . -3.0(2) ?
    O1 C2 N3 C6 . . . . 157.15(15) ?
    O1 C2 N3 C4 . . . . 0.8(2) ?
    C6 N3 C4 C5 . . . . -152.48(17) ?
    C2 N3 C4 C5 . . . . 1.34(19) ?
    C6 N3 C4 C15 . . . . 86.4(2) ?
    C2 N3 C4 C15 . . . . -119.80(17) ?
    C2 O1 C5 O5 . . . . -176.54(18) ?
    C2 O1 C5 C4 . . . . 4.0(2) ?
    N3 C4 C5 O5 . . . . 177.38(19) ?
    C15 C4 C5 O5 . . . . -60.6(3) ?
    N3 C4 C5 O1 . . . . -3.20(19) ?
    C15 C4 C5 O1 . . . . 118.80(17) ?
    C2 N3 C6 O6 . . . . 11.0(3) ?
    C4 N3 C6 O6 . . . . 163.56(17) ?
    C2 N3 C6 O7 . . . . -170.34(15) ?
    C4 N3 C6 O7 . . . . -17.8(2) ?
    O6 C6 O7 C8 . . . . 0.1(3) ?
    N3 C6 O7 C8 . . . . -178.52(15) ?
    C6 O7 C8 C9 . . . . 92.1(2) ?
    O7 C8 C9 C14 . . . . 117.2(2) ?
    O7 C8 C9 C10 . . . . -66.2(2) ?
    C14 C9 C10 C11 . . . . -1.4(3) ?
    C8 C9 C10 C11 . . . . -178.02(19) ?
    C9 C10 C11 C12 . . . . 1.8(3) ?
    C10 C11 C12 C13 . . . . -0.7(4) ?
    C11 C12 C13 C14 . . . . -0.8(4) ?
    C12 C13 C14 C9 . . . . 1.2(3) ?
    C10 C9 C14 C13 . . . . -0.1(3) ?
    C8 C9 C14 C13 . . . . 176.57(19) ?
    N3 C4 C15 C16 . . . . 62.4(2) ?
    C5 C4 C15 C16 . . . . -52.3(2) ?
    N3 C4 C15 C17 . . . . -172.49(16) ?
    C5 C4 C15 C17 . . . . 72.8(2) ?
loop_
    _geom_hbond_atom_site_label_D
    _geom_hbond_atom_site_label_H
    _geom_hbond_atom_site_label_A
    _geom_hbond_site_symmetry_A
    _geom_hbond_distance_DH
    _geom_hbond_distance_HA
    _geom_hbond_distance_DA
    _geom_hbond_angle_DHA
    _geom_hbond_publ_flag
    C2 H2A O5 1_455 0.97 2.32 3.258(2) 163.4 y
    C12 H12A Cg 4_455 0.93 3.37 3.963(3) 123.6 y
data_global
_journal_date_recd_electronic     2008-01-25
_journal_date_accepted     2008-02-14
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2008
_journal_volume     64
_journal_issue      4
_journal_page_first     o685
_journal_page_last     o685
_journal_paper_category     QO
_journal_coeditor_code     CF2183
_publ_contact_author_name     'Tang Guo'
_publ_contact_author_address
;
Key Laboratory for Chemical Biology of Fujian Province
Department of Chemistry
Xiamen University
Xiamen 361005
People's Republic of China
;
_publ_contact_author_email     t12g21@xmu.edu.cn
_publ_contact_author_fax     '86-592-2185780'
_publ_contact_author_phone     '86-592-2185780'
_publ_section_title
;
(4S)-Benzyl 4-isopropyl-5-oxo-1,3-oxazolidine-3-carboxylate
;
loop_
    _publ_author_name
    _publ_author_address
    'Wu, Jian-Bin'
;
Key Laboratory for Chemical Biology of Fujian Province
Department of Chemistry
Xiamen University
Xiamen 361005
People's Republic of China
;
    'Lin, Kan'
;
Key Laboratory for Chemical Biology of Fujian Province
Department of Chemistry
Xiamen University
Xiamen 361005
People's Republic of China
;
    'Guo, Jian-Nan'
;
Key Laboratory for Chemical Biology of Fujian Province
Department of Chemistry
Xiamen University
Xiamen 361005
People's Republic of China
;
    'Tang, Guo'
;
Key Laboratory for Chemical Biology of Fujian Province
Department of Chemistry
Xiamen University
Xiamen 361005
People's Republic of China
;
    'Zhao, Yu-Fen'
;
Key Laboratory for Chemical Biology of Fujian Province
Department of Chemistry
Xiamen University
Xiamen 361005
People's Republic of China
;
