##############################################################################
###                                                                        ###
###        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/  #
# cif/home.html                                                              #
#                                                                            #
# This file may be used for bona fide research purposes within the           #
# scientific community so long as proper attribution is given to the journal # 
# article from which it was obtained.                                        #
#                                                                            #
##############################################################################
                                             
data_global
_audit_creation_method     'from SHELXL97 CIF and IUCr SHELXL97-template'
_journal_date_recd_electronic     2008-04-17
_journal_date_accepted     2008-06-12
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2008
_journal_volume     64
_journal_issue      7
_journal_page_first     o1292
_journal_page_last     o1292
_journal_paper_category     QO
_journal_coeditor_code     BH2173
_publ_contact_author_name     'Guo, Cheng'
_publ_contact_author_address
;
Department of Applied Chemistry
College of Science
Nanjing University of Technolgy
Xinmofan Road No. 5
Nanjing 210009
People's Republic of China
;
_publ_contact_author_email     guocheng@njut.edu.cn
_publ_contact_author_fax     '86 25  83369345'
_publ_contact_author_phone     '86 25 83587448'
_publ_section_title
;\
(2S,3R)-2-[(4-Ethyl-2,3-dioxopiperazin-1-yl)carbonylamino]-3-\
hydroxybutyric acid monohydrate
;
loop_
    _publ_author_name
    _publ_author_address
    "Ji, Chun-xiang"
;
Department of Applied Chemistry
College of Science
Nanjing University of Technolgy
Xinmofan Road No. 5
Nanjing 210009
People's Republic of China
;
    "Cui, Yong-tao"
;
Department of Applied Chemistry
College of Science
Nanjing University of Technolgy
Xinmofan Road No. 5
Nanjing 210009
People's Republic of China
;
    "Yang, Dong-ling"
;
Nanjing FroChem Tech Co. Ltd.
Xinmofan Road No. 36 Nanjing
Nanjing 210009
People's Republic of China
;
    "Guo, Cheng"
;
Department of Applied Chemistry
College of Science
Nanjing University of Technolgy
Xinmofan Road No. 5
Nanjing 210009
People's Republic of China
;
data_I
_audit_creation_method     SHELXL97
_chemical_name_systematic
;
(2S,3R)-2-[(4-Ethyl-2,3-dioxopiperazin-1-yl)carbonylamino]-\
3-hydroxybutyric acid monohydrate
;
_chemical_name_common     ?
_chemical_formula_moiety     'C11 H17 N3 O6, H2 O'
_chemical_formula_sum     'C11 H19 N3 O7'
_chemical_formula_iupac     'C11 H17 N3 O6, H2 O'
_chemical_formula_weight     305.29
_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     9.4640(19)
_cell_length_b     11.389(2)
_cell_length_c     13.611(3)
_cell_angle_alpha     90.00
_cell_angle_beta     90.00
_cell_angle_gamma     90.00
_cell_volume     1467.1(5)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     25
_cell_measurement_theta_min     10
_cell_measurement_theta_max     13
_cell_measurement_temperature     293(2)
_exptl_crystal_description     block
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.40
_exptl_crystal_size_mid     0.30
_exptl_crystal_size_min     0.20
_exptl_crystal_density_diffrn     1.382
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     648
_exptl_absorpt_coefficient_mu     0.116
_exptl_absorpt_correction_type     psi-scan
_exptl_absorpt_process_details     '(North et al.,  1968)'
_exptl_absorpt_correction_T_min     0.9551
_exptl_absorpt_correction_T_max     0.9772
_exptl_special_details     ?
_diffrn_ambient_temperature     293(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     'Enraf--Nonius CAD-4'
_diffrn_measurement_method     ω/2θ
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     1519
_diffrn_reflns_av_R_equivalents     0.0000
_diffrn_reflns_av_sigmaI/netI     0.0264
_diffrn_reflns_theta_min     2.33
_diffrn_reflns_theta_max     25.14
_diffrn_reflns_theta_full     25.14
_diffrn_measured_fraction_theta_max     0.999
_diffrn_measured_fraction_theta_full     0.999
_diffrn_reflns_limit_h_min     0
_diffrn_reflns_limit_h_max     11
_diffrn_reflns_limit_k_min     0
_diffrn_reflns_limit_k_max     13
_diffrn_reflns_limit_l_min     0
_diffrn_reflns_limit_l_max     16
_diffrn_standards_number     3
_diffrn_standards_interval_count     200
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%     <1
_refine_special_details     ?
_reflns_number_total     1519
_reflns_number_gt     1287
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0505
_refine_ls_R_factor_gt     0.0411
_refine_ls_wR_factor_gt     0.0995
_refine_ls_wR_factor_ref     0.1054
_refine_ls_goodness_of_fit_ref     1.041
_refine_ls_restrained_S_all     1.041
_refine_ls_number_reflns     1519
_refine_ls_number_parameters     205
_refine_ls_number_restraints     2
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0652P)²+0.1558P] 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     0.159
_refine_diff_density_min     -0.157
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_extinction_coef     0.037(4)
_refine_ls_extinction_expression
                                  'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
_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 0.0016
                         '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     'CAD--4 Software (Enraf--Nonius, 1989)'
_computing_cell_refinement     'CAD--4 Software (Enraf--Nonius, 1989)'
_computing_data_reduction     'XCAD4 (Harms & Wocadlo, 1995)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics     'SHELXTL (Sheldrick, 2008)'
_computing_publication_material     'PLATON (Spek, 2003)'
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
    C C1 0.2982(5) 0.8688(4) 0.3149(3) 0.0802(14) Uani d . 1 . .
    H H1A 0.2231 0.9061 0.2793 0.120 Uiso calc R 1 . .
    H H1B 0.3779 0.9207 0.3183 0.120 Uiso calc R 1 . .
    H H1C 0.2666 0.8505 0.3802 0.120 Uiso calc R 1 . .
    C C2 0.3399(4) 0.7585(3) 0.2637(3) 0.0517(9) Uani d . 1 . .
    H H2A 0.2588 0.7066 0.2601 0.062 Uiso calc R 1 . .
    H H2B 0.3683 0.7771 0.1970 0.062 Uiso calc R 1 . .
    C C3 0.5900(3) 0.7122(3) 0.2851(2) 0.0401(7) Uani d . 1 . .
    C C4 0.7064(3) 0.6501(3) 0.3450(2) 0.0385(7) Uani d . 1 . .
    C C5 0.5156(3) 0.5303(3) 0.4161(3) 0.0549(10) Uani d . 1 . .
    H H5A 0.4893 0.4738 0.3659 0.066 Uiso calc R 1 . .
    H H5B 0.4997 0.4945 0.4798 0.066 Uiso calc R 1 . .
    C C6 0.4272(3) 0.6364(3) 0.4065(3) 0.0544(9) Uani d . 1 . .
    H H6B 0.3282 0.6145 0.4091 0.065 Uiso calc R 1 . .
    H H6C 0.4461 0.6891 0.4609 0.065 Uiso calc R 1 . .
    C C7 0.7632(3) 0.4841(3) 0.4570(2) 0.0403(7) Uani d . 1 . .
    C C8 1.0033(3) 0.4380(3) 0.5054(2) 0.0373(7) Uani d . 1 . .
    H H8A 0.9525 0.4006 0.5598 0.045 Uiso calc R 1 . .
    C C9 1.1128(3) 0.5210(3) 0.5489(2) 0.0390(7) Uani d . 1 . .
    C C10 1.0768(3) 0.3423(3) 0.4465(2) 0.0425(7) Uani d . 1 . .
    H H10A 1.1384 0.2984 0.4913 0.051 Uiso calc R 1 . .
    C C11 0.9774(4) 0.2570(3) 0.3990(3) 0.0570(9) Uani d . 1 . .
    H H11A 1.0306 0.1992 0.3633 0.085 Uiso calc R 1 . .
    H H11B 0.9161 0.2982 0.3547 0.085 Uiso calc R 1 . .
    H H11C 0.9219 0.2188 0.4487 0.085 Uiso calc R 1 . .
    N N1 0.4564(2) 0.6970(2) 0.31326(19) 0.0416(7) Uani d . 1 . .
    N N2 0.6683(3) 0.5610(2) 0.4054(2) 0.0397(6) Uani d . 1 . .
    N N3 0.9022(2) 0.5055(2) 0.44847(19) 0.0383(6) Uani d . 1 . .
    H H3A 0.9314 0.5594 0.4091 0.046 Uiso calc R 1 . .
    O O1 0.6257(2) 0.7700(3) 0.21398(19) 0.0635(8) Uani d . 1 . .
    O O2 0.8292(2) 0.6821(2) 0.33274(19) 0.0534(7) Uani d . 1 . .
    O O3 0.7145(3) 0.4047(2) 0.5047(2) 0.0648(8) Uani d . 1 . .
    O O4 1.1991(3) 0.4638(2) 0.6080(2) 0.0654(8) Uani d . 1 . .
    H H4 1.254(6) 0.501(4) 0.632(3) 0.072(15) Uiso d . 1 . .
    O O5 1.1208(2) 0.6236(2) 0.53094(18) 0.0506(6) Uani d . 1 . .
    O O6 1.1642(3) 0.4009(2) 0.3763(2) 0.0600(7) Uani d . 1 . .
    H H6 1.217(5) 0.354(4) 0.347(3) 0.064(12) Uiso d . 1 . .
    O O7 0.9118(3) 0.9195(3) 0.3221(2) 0.0663(8) Uani d D 1 . .
    H H7A 0.894(5) 0.847(2) 0.332(3) 0.080 Uiso d D 1 . .
    H H7B 0.909(5) 0.937(4) 0.2641(17) 0.080 Uiso d D 1 . .
_geom_special_details     ?
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
    C1 C2 . 1.491(5) ?
    C1 H1A . 0.9600 ?
    C1 H1B . 0.9600 ?
    C1 H1C . 0.9600 ?
    C2 N1 . 1.470(4) ?
    C2 H2A . 0.9700 ?
    C2 H2B . 0.9700 ?
    C3 O1 . 1.218(4) ?
    C3 N1 . 1.333(4) ?
    C3 C4 . 1.542(4) ?
    C4 O2 . 1.229(3) ?
    C4 N2 . 1.354(4) ?
    C5 C6 . 1.476(5) ?
    C5 N2 . 1.495(4) ?
    C5 H5A . 0.9700 ?
    C5 H5B . 0.9700 ?
    C6 N1 . 1.470(4) ?
    C6 H6B . 0.9700 ?
    C6 H6C . 0.9700 ?
    C7 O3 . 1.205(4) ?
    C7 N3 . 1.343(4) ?
    C7 N2 . 1.438(4) ?
    C8 N3 . 1.451(4) ?
    C8 C10 . 1.521(4) ?
    C8 C9 . 1.522(4) ?
    C8 H8A . 0.9800 ?
    C9 O5 . 1.196(4) ?
    C9 O4 . 1.319(4) ?
    C10 O6 . 1.430(4) ?
    C10 C11 . 1.499(5) ?
    C10 H10A . 0.9800 ?
    C11 H11A . 0.9600 ?
    C11 H11B . 0.9600 ?
    C11 H11C . 0.9600 ?
    N3 H3A . 0.8600 ?
    O4 H4 . 0.75(5) ?
    O6 H6 . 0.83(4) ?
    O7 H7A . 0.85(2) ?
    O7 H7B . 0.815(19) ?
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 C1 H1A . . 109.5 ?
    C2 C1 H1B . . 109.5 ?
    H1A C1 H1B . . 109.5 ?
    C2 C1 H1C . . 109.5 ?
    H1A C1 H1C . . 109.5 ?
    H1B C1 H1C . . 109.5 ?
    N1 C2 C1 . . 112.7(3) ?
    N1 C2 H2A . . 109.1 ?
    C1 C2 H2A . . 109.1 ?
    N1 C2 H2B . . 109.1 ?
    C1 C2 H2B . . 109.1 ?
    H2A C2 H2B . . 107.8 ?
    O1 C3 N1 . . 124.2(3) ?
    O1 C3 C4 . . 118.0(3) ?
    N1 C3 C4 . . 117.8(3) ?
    O2 C4 N2 . . 123.8(3) ?
    O2 C4 C3 . . 117.8(3) ?
    N2 C4 C3 . . 118.3(2) ?
    C6 C5 N2 . . 110.3(3) ?
    C6 C5 H5A . . 109.6 ?
    N2 C5 H5A . . 109.6 ?
    C6 C5 H5B . . 109.6 ?
    N2 C5 H5B . . 109.6 ?
    H5A C5 H5B . . 108.1 ?
    N1 C6 C5 . . 110.7(3) ?
    N1 C6 H6B . . 109.5 ?
    C5 C6 H6B . . 109.5 ?
    N1 C6 H6C . . 109.5 ?
    C5 C6 H6C . . 109.5 ?
    H6B C6 H6C . . 108.1 ?
    O3 C7 N3 . . 123.9(3) ?
    O3 C7 N2 . . 118.8(3) ?
    N3 C7 N2 . . 117.3(3) ?
    N3 C8 C10 . . 113.6(2) ?
    N3 C8 C9 . . 109.1(2) ?
    C10 C8 C9 . . 109.8(2) ?
    N3 C8 H8A . . 108.1 ?
    C10 C8 H8A . . 108.1 ?
    C9 C8 H8A . . 108.1 ?
    O5 C9 O4 . . 124.6(3) ?
    O5 C9 C8 . . 124.8(3) ?
    O4 C9 C8 . . 110.6(3) ?
    O6 C10 C11 . . 112.2(3) ?
    O6 C10 C8 . . 106.4(3) ?
    C11 C10 C8 . . 113.9(3) ?
    O6 C10 H10A . . 108.1 ?
    C11 C10 H10A . . 108.1 ?
    C8 C10 H10A . . 108.1 ?
    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 ?
    C3 N1 C2 . . 121.2(3) ?
    C3 N1 C6 . . 119.2(3) ?
    C2 N1 C6 . . 118.6(2) ?
    C4 N2 C7 . . 125.9(2) ?
    C4 N2 C5 . . 119.5(3) ?
    C7 N2 C5 . . 114.4(2) ?
    C7 N3 C8 . . 120.2(3) ?
    C7 N3 H3A . . 119.9 ?
    C8 N3 H3A . . 119.9 ?
    C9 O4 H4 . . 115(4) ?
    C10 O6 H6 . . 111(3) ?
    H7A O7 H7B . . 113(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
    O1 C3 C4 O2 . . . . 16.1(5) ?
    N1 C3 C4 O2 . . . . -165.3(3) ?
    O1 C3 C4 N2 . . . . -161.7(3) ?
    N1 C3 C4 N2 . . . . 16.9(4) ?
    N2 C5 C6 N1 . . . . 55.3(4) ?
    N3 C8 C9 O5 . . . . -6.4(4) ?
    C10 C8 C9 O5 . . . . 118.6(3) ?
    N3 C8 C9 O4 . . . . 174.5(3) ?
    C10 C8 C9 O4 . . . . -60.4(3) ?
    N3 C8 C10 O6 . . . . 67.5(3) ?
    C9 C8 C10 O6 . . . . -54.9(3) ?
    N3 C8 C10 C11 . . . . -56.5(4) ?
    C9 C8 C10 C11 . . . . -179.0(3) ?
    O1 C3 N1 C2 . . . . -5.0(5) ?
    C4 C3 N1 C2 . . . . 176.5(3) ?
    O1 C3 N1 C6 . . . . -173.2(3) ?
    C4 C3 N1 C6 . . . . 8.3(4) ?
    C1 C2 N1 C3 . . . . -95.7(4) ?
    C1 C2 N1 C6 . . . . 72.6(4) ?
    C5 C6 N1 C3 . . . . -44.8(4) ?
    C5 C6 N1 C2 . . . . 146.7(3) ?
    O2 C4 N2 C7 . . . . -6.0(5) ?
    C3 C4 N2 C7 . . . . 171.7(3) ?
    O2 C4 N2 C5 . . . . 179.1(3) ?
    C3 C4 N2 C5 . . . . -3.2(4) ?
    O3 C7 N2 C4 . . . . -176.4(3) ?
    N3 C7 N2 C4 . . . . 3.4(5) ?
    O3 C7 N2 C5 . . . . -1.3(5) ?
    N3 C7 N2 C5 . . . . 178.5(3) ?
    C6 C5 N2 C4 . . . . -32.7(5) ?
    C6 C5 N2 C7 . . . . 151.8(3) ?
    O3 C7 N3 C8 . . . . -5.7(5) ?
    N2 C7 N3 C8 . . . . 174.5(2) ?
    C10 C8 N3 C7 . . . . 101.8(3) ?
    C9 C8 N3 C7 . . . . -135.4(3) ?
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
    N3 H3A O2 . 0.86 1.99 2.647(3) 132.0 yes
    O7 H7A O2 . 0.85(2) 1.98(2) 2.817(4) 169(5) yes
    O4 H4 O7 4_566 0.75(5) 1.85(5) 2.593(4) 170(5) yes
    O6 H6 O1 3_745 0.83(4) 1.95(4) 2.772(3) 167(4) yes
    O7 H7B O6 3_755 0.815(19) 2.07(3) 2.803(4) 149(4) yes
