##############################################################################
###                                                                        ###
###        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 2.1.    #
#                                                                            #
# 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/  #
# cif/home.html                                                              #
#                                                                            #
#            Copyright International Union of Crystallography                #
#                                                                            #
##############################################################################
                                             
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
;
_chemical_name_common     ?
_chemical_formula_moiety     'C8 H8 O3, C3 H7 N O2'
_chemical_formula_sum     'C11 H15 N O5'
_chemical_formula_iupac     'C8 H8 O3, C3 H7 N O2'
_chemical_formula_weight     241.24
_chemical_melting_point     ?
_symmetry_cell_setting     Monoclinic
_symmetry_space_group_name_H-M     'C 2'
_symmetry_space_group_name_Hall     'C 2y'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, y, -z'
    'x+1/2, y+1/2, z'
    '-x+1/2, y+1/2, -z'
_cell_length_a     17.795(4)
_cell_length_b     5.394(2)
_cell_length_c     12.431(2)
_cell_angle_alpha     90.00
_cell_angle_beta     100.650(10)
_cell_angle_gamma     90.00
_cell_volume     1172.7(5)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     20
_cell_measurement_theta_min     5.5
_cell_measurement_theta_max     9.8
_cell_measurement_temperature     295(2)
_exptl_crystal_description     prism
_exptl_crystal_colour     colorless
_exptl_crystal_size_max     0.4
_exptl_crystal_size_mid     0.4
_exptl_crystal_size_min     0.2
_exptl_crystal_density_diffrn     1.366
_exptl_crystal_density_meas     'not measured'
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     512
_exptl_absorpt_coefficient_mu     0.108
_exptl_absorpt_correction_type     none
_exptl_absorpt_process_details     none
_exptl_special_details
;
;
_diffrn_ambient_temperature     295(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Rigaku AFC-7S'
_diffrn_measurement_method     ω/2θ
_diffrn_reflns_number     1928
_diffrn_reflns_av_R_equivalents     0.017
_diffrn_reflns_av_sigmaI/netI     0.027
_diffrn_reflns_theta_min     1.7
_diffrn_reflns_theta_max     27.5
_diffrn_reflns_theta_full     27.5
_diffrn_measured_fraction_theta_max     1.00
_diffrn_measured_fraction_theta_full     1.00
_diffrn_reflns_limit_h_min     -1
_diffrn_reflns_limit_h_max     22
_diffrn_reflns_limit_k_min     -7
_diffrn_reflns_limit_k_max     1
_diffrn_reflns_limit_l_min     -16
_diffrn_reflns_limit_l_max     15
_diffrn_standards_number     3
_diffrn_standards_interval_count     150
_diffrn_standards_decay_%     0.6
_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     1484
_reflns_number_gt     1276
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.063
_refine_ls_R_factor_gt     0.054
_refine_ls_wR_factor_gt     0.146
_refine_ls_wR_factor_ref     0.154
_refine_ls_goodness_of_fit_ref     1.062
_refine_ls_restrained_S_all     1.062
_refine_ls_number_reflns     1484
_refine_ls_number_parameters     136
_refine_ls_number_restraints     1
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
       'calc w = 1/[σ²(Fo²)+(0.0812P)²+1.03P] 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     0.001
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.35
_refine_diff_density_min     -0.33
_refine_ls_extinction_method     none
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'
_computing_data_collection
;
MSC/AFC Diffractometer Control Software
(Molecular Structure Corporation, 1992)
;
_computing_cell_refinement     'MSC/AFC Diffractometer Control Software'
_computing_data_reduction     'TEXSAN (Molecular Structure Corporation, 1985)'
_computing_structure_solution     'SIR-2 (Altomare et al., 1993)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 1997)'
_computing_molecular_graphics     'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material     'WinGX (Farrugia, 1999)'
loop_
    _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
    _atom_site_type_symbol
    O1 0.71606(13) 0.2376(5) 0.1896(2) 0.0459(6) Uani d . 1 B . O
    H1A 0.7121 0.0861 0.1878 0.055 Uiso calc R 1 . . H
    O2 0.57574(13) 0.7041(5) 0.1353(2) 0.0470(6) Uani d . 1 . . O
    H2A 0.5431 0.5991 0.1395 0.056 Uiso calc R 1 . . H
    O3 0.70046(13) 0.7252(5) 0.1586(2) 0.0424(6) Uani d . 1 . . O
    C1 0.64173(18) 0.6087(6) 0.1633(3) 0.0323(7) Uani d . 1 B . C
    C2 0.64601(18) 0.3442(6) 0.2061(3) 0.0336(7) Uani d . 1 . . C
    H2 0.6029 0.2479 0.1665 0.040 Uiso calc R 1 A 1 H
    C3A 0.6438(4) 0.3447(14) 0.3296(4) 0.0396(10) Uiso d PG 0.52 B 1 C
    C4A 0.6829(4) 0.5255(12) 0.3975(5) 0.0489(17) Uiso d PG 0.52 B 1 C
    H4A 0.7097 0.6488 0.3684 0.059 Uiso calc PR 0.52 B 1 H
    C5A 0.6820(4) 0.5220(13) 0.5091(4) 0.062(2) Uiso d PG 0.52 B 1 C
    H5A 0.7082 0.6430 0.5545 0.074 Uiso calc PR 0.52 B 1 H
    C6A 0.6420(5) 0.3377(16) 0.5527(4) 0.067(4) Uiso d PG 0.52 B 1 C
    H6A 0.6414 0.3353 0.6273 0.081 Uiso calc PR 0.52 B 1 H
    C7A 0.6029(4) 0.1569(14) 0.4847(6) 0.064(3) Uiso d PG 0.52 B 1 C
    H7A 0.5761 0.0335 0.5139 0.077 Uiso calc PR 0.52 B 1 H
    C8A 0.6038(4) 0.1604(13) 0.3731(6) 0.054(3) Uiso d PG 0.52 B 1 C
    H8A 0.5777 0.0394 0.3277 0.064 Uiso calc PR 0.52 B 1 H
    C3B 0.6455(9) 0.350(4) 0.3302(10) 0.0396(10) Uiso d PG 0.22 B 2 C
    C4B 0.7146(7) 0.378(5) 0.4023(14) 0.093(8) Uiso d PG 0.22 B 2 C
    H4B 0.7601 0.3858 0.3756 0.112 Uiso calc PR 0.22 B 2 H
    C5B 0.7158(9) 0.396(6) 0.5141(13) 0.119(12) Uiso d PG 0.22 B 2 C
    H5B 0.7621 0.4153 0.5623 0.143 Uiso calc PR 0.22 B 2 H
    C6B 0.6479(11) 0.385(6) 0.5540(10) 0.080(12) Uiso d PG 0.22 B 2 C
    H6B 0.6487 0.3971 0.6288 0.096 Uiso calc PR 0.22 B 2 H
    C7B 0.5787(9) 0.357(5) 0.4819(13) 0.085(7) Uiso d PG 0.22 B 2 C
    H7B 0.5333 0.3492 0.5086 0.102 Uiso calc PR 0.22 B 2 H
    C8B 0.5775(7) 0.339(4) 0.3701(12) 0.083(7) Uiso d PG 0.22 B 2 C
    H8B 0.5313 0.3197 0.3219 0.100 Uiso calc PR 0.22 B 2 H
    C3C 0.6308(9) 0.350(3) 0.3168(8) 0.0396(10) Uiso d PG 0.26 B 3 C
    C4C 0.6507(8) 0.551(3) 0.3865(10) 0.074(5) Uiso d PG 0.26 B 3 C
    H4C 0.6707 0.6933 0.3607 0.089 Uiso calc PR 0.26 B 3 H
    C5C 0.6407(8) 0.538(3) 0.4946(10) 0.084(6) Uiso d PG 0.26 B 3 C
    H5C 0.6540 0.6718 0.5412 0.100 Uiso calc PR 0.26 B 3 H
    C6C 0.6108(9) 0.324(3) 0.5331(9) 0.056(4) Uiso d PG 0.26 B 3 C
    H6C 0.6041 0.3155 0.6054 0.067 Uiso calc PR 0.26 B 3 H
    C7C 0.5908(10) 0.124(3) 0.4634(12) 0.084(8) Uiso d PG 0.26 B 3 C
    H7C 0.5708 -0.0191 0.4891 0.101 Uiso calc PR 0.26 B 3 H
    C8C 0.6008(10) 0.137(3) 0.3553(11) 0.069(7) Uiso d PG 0.26 B 3 C
    H8C 0.5875 0.0024 0.3086 0.083 Uiso calc PR 0.26 B 3 H
    O4 0.33578(14) 0.4495(5) 0.0742(2) 0.0455(7) Uani d . 1 . . O
    O5 0.46148(14) 0.4403(5) 0.1211(3) 0.0507(7) Uani d . 1 . . O
    N 0.32475(14) 0.9385(5) 0.0681(2) 0.0341(6) Uani d . 1 . . N
    H3A 0.3271 1.1031 0.0727 0.051 Uiso calc R 1 . . H
    H3B 0.2882 0.8832 0.1022 0.051 Uiso calc R 1 . . H
    H3C 0.3142 0.8935 -0.0020 0.051 Uiso calc R 1 . . H
    C9 0.39752(18) 0.5525(6) 0.1028(3) 0.0327(7) Uani d . 1 . . C
    C10 0.39911(17) 0.8317(6) 0.1203(3) 0.0317(7) Uani d . 1 . . C
    H10 0.4398 0.9042 0.0870 0.038 Uiso calc R 1 . . H
    C11 0.4137(2) 0.8915(9) 0.2413(3) 0.0542(10) Uani d . 1 . . C
    H11A 0.4260 1.0641 0.2517 0.081 Uiso calc R 1 . . H
    H11B 0.4556 0.7932 0.2783 0.081 Uiso calc R 1 . . H
    H11C 0.3687 0.8550 0.2708 0.081 Uiso calc R 1 . . H
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 0.0432(13) 0.0249(12) 0.0753(16) 0.0072(11) 0.0258(11) 0.0048(13)
    O2 0.0320(11) 0.0319(12) 0.0777(16) 0.0038(11) 0.0122(10) 0.0099(14)
    O3 0.0356(12) 0.0256(12) 0.0698(15) -0.0005(11) 0.0195(10) 0.0030(12)
    C1 0.0334(16) 0.0247(15) 0.0413(16) 0.0000(13) 0.0135(12) -0.0025(13)
    C2 0.0313(15) 0.0231(14) 0.0483(17) -0.0013(13) 0.0121(12) 0.0002(14)
    O4 0.0329(12) 0.0208(11) 0.0810(18) -0.0039(10) 0.0061(11) -0.0020(12)
    O5 0.0341(12) 0.0279(12) 0.0899(19) 0.0075(11) 0.0110(11) 0.0061(13)
    N 0.0307(13) 0.0221(12) 0.0499(15) 0.0014(12) 0.0083(11) -0.0003(12)
    C9 0.0292(15) 0.0227(15) 0.0471(17) 0.0012(12) 0.0096(13) 0.0006(13)
    C10 0.0259(14) 0.0221(14) 0.0477(17) -0.0010(12) 0.0088(12) -0.0035(14)
    C11 0.057(2) 0.049(2) 0.053(2) 0.0018(19) 0.0009(17) -0.0112(19)
_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 C2 . 1.422(4) y
    O1 H1A . 0.8200 ?
    O2 C1 . 1.270(4) y
    O2 H2A . 0.8200 ?
    O3 C1 . 1.230(4) y
    C1 C2 . 1.519(5) ?
    C2 C3C . 1.451(10) ?
    C2 C3A . 1.543(6) ?
    C2 C3B . 1.546(13) ?
    C2 H2 . 0.9800 ?
    C3A C4A . 1.3900 ?
    C3A C8A . 1.3900 ?
    C4A C5A . 1.3900 ?
    C4A H4A . 0.9300 ?
    C5A C6A . 1.3900 ?
    C5A H5A . 0.9300 ?
    C6A C7A . 1.3900 ?
    C6A H6A . 0.9300 ?
    C7A C8A . 1.3900 ?
    C7A H7A . 0.9300 ?
    C8A H8A . 0.9300 ?
    C3B C4B . 1.3900 ?
    C3B C8B . 1.3900 ?
    C4B C5B . 1.3900 ?
    C4B H4B . 0.9300 ?
    C5B C6B . 1.3900 ?
    C5B H5B . 0.9300 ?
    C6B C7B . 1.3900 ?
    C6B H6B . 0.9300 ?
    C7B C8B . 1.3900 ?
    C7B H7B . 0.9300 ?
    C8B H8B . 0.9300 ?
    C3C C4C . 1.3900 ?
    C3C C8C . 1.3900 ?
    C4C C5C . 1.3900 ?
    C4C H4C . 0.9300 ?
    C5C C6C . 1.3900 ?
    C5C H5C . 0.9300 ?
    C6C C7C . 1.3900 ?
    C6C H6C . 0.9300 ?
    C7C C8C . 1.3900 ?
    C7C H7C . 0.9300 ?
    C8C H8C . 0.9300 ?
    O4 C9 . 1.224(4) y
    O5 C9 . 1.272(4) y
    N C10 . 1.479(4) y
    N H3A . 0.8900 ?
    N H3B . 0.8900 ?
    N H3C . 0.8900 ?
    C9 C10 . 1.521(4) y
    C10 C11 . 1.514(5) y
    C10 H10 . 0.9800 ?
    C11 H11A . 0.9600 ?
    C11 H11B . 0.9600 ?
    C11 H11C . 0.9600 ?
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
    C2 O1 H1A . . 109.5 ?
    C1 O2 H2A . . 109.5 ?
    O3 C1 O2 . . 122.0(3) ?
    O3 C1 C2 . . 120.5(3) ?
    O2 C1 C2 . . 117.4(3) ?
    O1 C2 C3C . . 117.9(7) ?
    O1 C2 C1 . . 108.6(3) ?
    C3C C2 C1 . . 107.8(7) ?
    O1 C2 C3A . . 109.1(4) ?
    C3C C2 C3A . . 9.2(8) ?
    C1 C2 C3A . . 109.7(4) ?
    O1 C2 C3B . . 108.6(7) ?
    C3C C2 C3B . . 10.2(9) ?
    C1 C2 C3B . . 108.8(8) ?
    C3A C2 C3B . . 1.5(8) ?
    O1 C2 H2 . . 109.8 ?
    C3C C2 H2 . . 102.8 ?
    C1 C2 H2 . . 109.8 ?
    C3A C2 H2 . . 109.8 ?
    C3B C2 H2 . . 111.3 ?
    C4A C3A C8A . . 120.0 ?
    C4A C3A C2 . . 120.3(4) ?
    C8A C3A C2 . . 119.7(4) ?
    C3A C4A C5A . . 120.0 ?
    C3A C4A H4A . . 120.0 ?
    C5A C4A H4A . . 120.0 ?
    C6A C5A C4A . . 120.0 ?
    C6A C5A H5A . . 120.0 ?
    C4A C5A H5A . . 120.0 ?
    C5A C6A C7A . . 120.0 ?
    C5A C6A H6A . . 120.0 ?
    C7A C6A H6A . . 120.0 ?
    C6A C7A C8A . . 120.0 ?
    C6A C7A H7A . . 120.0 ?
    C8A C7A H7A . . 120.0 ?
    C7A C8A C3A . . 120.0 ?
    C7A C8A H8A . . 120.0 ?
    C3A C8A H8A . . 120.0 ?
    C4B C3B C8B . . 120.0 ?
    C4B C3B C2 . . 118.5(10) ?
    C8B C3B C2 . . 121.4(10) ?
    C3B C4B C5B . . 120.0 ?
    C3B C4B H4B . . 120.0 ?
    C5B C4B H4B . . 120.0 ?
    C6B C5B C4B . . 120.0 ?
    C6B C5B H5B . . 120.0 ?
    C4B C5B H5B . . 120.0 ?
    C5B C6B C7B . . 120.0 ?
    C5B C6B H6B . . 120.0 ?
    C7B C6B H6B . . 120.0 ?
    C6B C7B C8B . . 120.0 ?
    C6B C7B H7B . . 120.0 ?
    C8B C7B H7B . . 120.0 ?
    C7B C8B C3B . . 120.0 ?
    C7B C8B H8B . . 120.0 ?
    C3B C8B H8B . . 120.0 ?
    C4C C3C C8C . . 120.0 ?
    C4C C3C C2 . . 122.5(10) ?
    C8C C3C C2 . . 117.3(10) ?
    C5C C4C C3C . . 120.0 ?
    C5C C4C H4C . . 120.0 ?
    C3C C4C H4C . . 120.0 ?
    C6C C5C C4C . . 120.0 ?
    C6C C5C H5C . . 120.0 ?
    C4C C5C H5C . . 120.0 ?
    C5C C6C C7C . . 120.0 ?
    C5C C6C H6C . . 120.0 ?
    C7C C6C H6C . . 120.0 ?
    C6C C7C C8C . . 120.0 ?
    C6C C7C H7C . . 120.0 ?
    C8C C7C H7C . . 120.0 ?
    C7C C8C C3C . . 120.0 ?
    C7C C8C H8C . . 120.0 ?
    C3C C8C H8C . . 120.0 ?
    C10 N H3A . . 109.5 ?
    C10 N H3B . . 109.5 ?
    H3A N H3B . . 109.5 ?
    C10 N H3C . . 109.5 ?
    H3A N H3C . . 109.5 ?
    H3B N H3C . . 109.5 ?
    O4 C9 O5 . . 124.2(3) ?
    O4 C9 C10 . . 118.9(3) ?
    O5 C9 C10 . . 116.9(3) ?
    N C10 C11 . . 109.2(3) ?
    N C10 C9 . . 109.4(3) ?
    C11 C10 C9 . . 110.4(3) ?
    N C10 H10 . . 109.3 ?
    C11 C10 H10 . . 109.3 ?
    C9 C10 H10 . . 109.3 ?
    C10 C11 H11A . . 109.5 ?
    C10 C11 H11B . . 109.5 ?
    H11A C11 H11B . . 109.5 ?
    C10 C11 H11C . . 109.5 ?
    H11A C11 H11C . . 109.5 ?
    H11B C11 H11C . . 109.5 ?
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
    O1 H1A O3 1_545 0.82 1.98 2.797(4) 171 y
    O2 H2A O5 . 0.82 1.67 2.461(4) 163 y
    N H3A O4 1_565 0.89 1.87 2.763(4) 176 y
    N H3B O1 3_455 0.89 1.99 2.877(4) 173 y
    N H3C O3 2_655 0.89 2.12 3.000(4) 169 y
data_global
_journal_date_recd_electronic     2003-12-22
_journal_date_accepted     2004-01-20
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2004
_journal_volume     60
_journal_issue      2
_journal_page_first     o269
_journal_page_last     o271
_journal_paper_category     EO
_publ_contact_author_name     'Dr. Duanjun Xu'
_publ_contact_author_address
;
Department of Chemistry
Zhejiang University
Hangzhou, 310027
P. R. China
;
_publ_contact_author_email     xudj@mail.hz.zj.cn
_publ_section_title
;
(S)-Alanine--(S)-mandelic acid (1/1)
;
loop_
    _publ_author_name
    _publ_author_address
    'Zi-Qiang Hu'
;
Department of Chemistry
Zhejiang University
People's Republic of China
;
    'Duan-Jun Xu'
;
Department of Chemistry
Zhejiang University
People's Republic of China
;
    'Yuan-Zhi Xu'
;
Department of Chemistry
Zhejiang University
People's Republic of China
;
