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###                                                                        ###
###        Electronic paper (Acta Crystallographica Section E)             ###
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#                                                                            #
# 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                                                              #
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data_global
_audit_creation_method     'manual editing of form.cif'
_journal_data_validation_number     ?
_journal_date_recd_electronic     2007-11-16
_journal_date_accepted     2007-12-27
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2008
_journal_volume     64
_journal_issue      2
_journal_page_first     o446
_journal_page_last     o446
_journal_paper_category     QO
_journal_coeditor_code     SI2055
_publ_contact_author_name     'Zu-Guang Li'
_publ_contact_author_address
;
   College of Chemical Engineering and Materials Science
   Zhejiang University of Technology
   Hangzhou 310014
   People's Republic of China
;
_publ_contact_author_email     zgdlzg@sina.com
_publ_contact_author_fax     '++86-571-88320418'
_publ_contact_author_phone     '?'
_publ_section_title
;
L-Glutamic acid hydrochloride at 153 K
;
loop_
    _publ_author_name
    _publ_author_address
    'Yi Jian Zhang'
;
   College of Materials Chemistry and Chemical Engineering
   Hangzhou Normal University
   Hangzhou 310036
   People's Republic of China
;
    'Zhan Shu'
;
   College of Pharmaceutical Sciences
   Zhejiang University of Technology
   Hangzhou 310014
   People's Republic of China
;
    'Wei Xu'
;
   College of Pharmaceutical Sciences
   Zhejiang University of Technology
   Hangzhou 310014
   People's Republic of China
;
    'Gang Chen'
;
   College of Pharmaceutical Sciences
   Zhejiang University of Technology
   Hangzhou 310014
   People's Republic of China
;
    'Zu-Guang Li'
;
   College of Chemical Engineering and Materials Science
   Zhejiang University of Technology
   Hangzhou 310014
   People's Republic of China
;
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
(S)-1,3-dicarboxypropanaminium chloride
;
_chemical_name_common     'L-Glutamic acid Hydrochloride'
_chemical_formula_moiety     'C5 H10 N O4 +, Cl -'
_chemical_formula_sum     'C5 H10 Cl1 N1 O4'
_chemical_formula_iupac     'C5 H10 N O4 +, Cl -'
_chemical_formula_weight     183.59
_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     5.10160(10)
_cell_length_b     11.6386(4)
_cell_length_c     13.2500(3)
_cell_angle_alpha     90.00
_cell_angle_beta     90.00
_cell_angle_gamma     90.00
_cell_volume     786.73(4)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     7746
_cell_measurement_theta_min     3.08
_cell_measurement_theta_max     27.50
_cell_measurement_temperature     153(2)
_exptl_crystal_description     Block
_exptl_crystal_colour     Colorless
_exptl_crystal_size_max     0.49
_exptl_crystal_size_mid     0.48
_exptl_crystal_size_min     0.35
_exptl_crystal_density_diffrn     1.550
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     384
_exptl_absorpt_coefficient_mu     0.453
_exptl_absorpt_correction_type     psi-scan
_exptl_absorpt_process_details     '(SHELXTL; Bruker, 1998)'
_exptl_absorpt_correction_T_min     0.8085
_exptl_absorpt_correction_T_max     0.8575
_exptl_special_details
;
 ?
;
_diffrn_ambient_temperature     153(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     'Siemens P4'
_diffrn_measurement_method     ω
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     7742
_diffrn_reflns_av_R_equivalents     0.0160
_diffrn_reflns_av_sigmaI/netI     0.0129
_diffrn_reflns_theta_min     3.07
_diffrn_reflns_theta_max     27.47
_diffrn_reflns_theta_full     27.47
_diffrn_measured_fraction_theta_max     0.994
_diffrn_measured_fraction_theta_full     0.994
_diffrn_reflns_limit_h_min     -6
_diffrn_reflns_limit_h_max     6
_diffrn_reflns_limit_k_min     -15
_diffrn_reflns_limit_k_max     15
_diffrn_reflns_limit_l_min     -15
_diffrn_reflns_limit_l_max     16
_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     1798
_reflns_number_gt     1775
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0196
_refine_ls_R_factor_gt     0.0194
_refine_ls_wR_factor_gt     0.0550
_refine_ls_wR_factor_ref     0.0551
_refine_ls_goodness_of_fit_ref     1.152
_refine_ls_restrained_S_all     1.152
_refine_ls_number_reflns     1798
_refine_ls_number_parameters     101
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
              'w=1/[σ²(Fo²)+(0.0313P)²+0.1681P] 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     0.287
_refine_diff_density_min     -0.250
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 1997)'
_refine_ls_extinction_coef     0.058(4)
_refine_ls_extinction_expression
                                  'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
_refine_ls_abs_structure_details     'Flack (1983), 725 Friedel pairs'
_refine_ls_abs_structure_Flack     0.02(4)
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'
    'Cl' 'Cl' 0.1484 0.1585
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'PROCESS-AUTO (Rigaku, 1998)'
_computing_cell_refinement     'PROCESS-AUTO (Rigaku, 1998)'
_computing_data_reduction     'CrystalStructure (Rigaku/MSC, 2004)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 1997)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 1997)'
_computing_molecular_graphics     'SHELXTL (Bruker, 1998)'
_computing_publication_material     'SHELXTL (Bruker, 1998)'
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
    Cl Cl1 1.05471(5) 0.93130(2) 0.26203(2) 0.01395(9) Uani d . 1 . .
    O O1 0.4387(2) 0.53632(7) 0.07337(7) 0.0205(2) Uani d . 1 . .
    H H1 0.3341 0.5102 0.0301 0.031 Uiso calc R 1 . .
    O O2 0.20701(18) 0.69846(7) 0.05162(7) 0.0161(2) Uani d . 1 . .
    O O3 0.4214(2) 0.55251(8) 0.45585(6) 0.0204(2) Uani d . 1 . .
    O O4 0.70041(18) 0.67059(8) 0.53439(6) 0.0167(2) Uani d . 1 . .
    H H4 0.6454 0.6361 0.5859 0.025 Uiso calc R 1 . .
    N N1 0.5606(2) 0.82410(8) 0.15658(7) 0.0120(2) Uani d . 1 . .
    H H1A 0.6701 0.8569 0.2025 0.018 Uiso calc R 1 . .
    H H1B 0.3939 0.8490 0.1676 0.018 Uiso calc R 1 . .
    H H1C 0.6117 0.8442 0.0932 0.018 Uiso calc R 1 . .
    C C1 0.3864(2) 0.64491(10) 0.08985(9) 0.0116(2) Uani d . 1 . .
    C C2 0.5705(2) 0.69659(9) 0.16728(8) 0.0102(2) Uani d . 1 . .
    H H2 0.7532 0.6689 0.1547 0.012 Uiso calc R 1 . .
    C C3 0.4798(2) 0.65720(10) 0.27187(8) 0.0115(2) Uani d . 1 . .
    H H3A 0.3074 0.6926 0.2863 0.014 Uiso calc R 1 . .
    H H3B 0.4550 0.5728 0.2705 0.014 Uiso calc R 1 . .
    C C4 0.6668(2) 0.68690(10) 0.35714(8) 0.0124(2) Uani d . 1 . .
    H H4A 0.8458 0.6610 0.3395 0.015 Uiso calc R 1 . .
    H H4B 0.6712 0.7713 0.3666 0.015 Uiso calc R 1 . .
    C C5 0.5815(3) 0.63012(9) 0.45392(8) 0.0119(2) Uani d . 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
    Cl1 0.01329(14) 0.01559(13) 0.01296(14) -0.00183(11) -0.00097(10)
                                                                     0.00137(10)
    O1 0.0232(4) 0.0145(4) 0.0238(4) 0.0019(4) -0.0111(4) -0.0082(3)
    O2 0.0166(4) 0.0164(4) 0.0153(4) 0.0004(3) -0.0052(3) 0.0000(3)
    O3 0.0284(5) 0.0194(5) 0.0134(4) -0.0119(4) 0.0021(4) 0.0018(3)
    O4 0.0214(5) 0.0196(4) 0.0089(4) -0.0053(4) -0.0014(4) 0.0029(3)
    N1 0.0134(4) 0.0119(4) 0.0105(4) -0.0028(4) -0.0012(4) 0.0014(3)
    C1 0.0119(6) 0.0148(5) 0.0081(5) -0.0022(4) 0.0004(4) 0.0006(4)
    C2 0.0107(5) 0.0100(5) 0.0101(5) -0.0009(5) -0.0006(5) -0.0006(4)
    C3 0.0121(5) 0.0128(5) 0.0096(5) -0.0025(4) 0.0006(4) 0.0016(4)
    C4 0.0138(5) 0.0146(5) 0.0089(5) -0.0039(5) 0.0011(4) 0.0014(4)
    C5 0.0139(6) 0.0114(5) 0.0105(5) 0.0002(4) 0.0007(5) 0.0005(4)
_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 C1 . 1.3101(15) yes
    O1 H1 . 0.8400 ?
    O2 C1 . 1.2176(15) yes
    O3 C5 . 1.2183(15) yes
    O4 C5 . 1.3139(14) yes
    O4 H4 . 0.8400 ?
    N1 C2 . 1.4916(14) yes
    N1 H1A . 0.9100 ?
    N1 H1B . 0.9100 ?
    N1 H1C . 0.9100 ?
    C1 C2 . 1.5156(16) yes
    C2 C3 . 1.5312(15) yes
    C2 H2 . 1.0000 ?
    C3 C4 . 1.5184(16) yes
    C3 H3A . 0.9900 ?
    C3 H3B . 0.9900 ?
    C4 C5 . 1.5066(15) yes
    C4 H4A . 0.9900 ?
    C4 H4B . 0.9900 ?
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
    C1 O1 H1 . . 109.5 ?
    C5 O4 H4 . . 109.5 ?
    C2 N1 H1A . . 109.5 ?
    C2 N1 H1B . . 109.5 ?
    H1A N1 H1B . . 109.5 ?
    C2 N1 H1C . . 109.5 ?
    H1A N1 H1C . . 109.5 ?
    H1B N1 H1C . . 109.5 ?
    O2 C1 O1 . . 125.29(11) yes
    O2 C1 C2 . . 122.99(10) yes
    O1 C1 C2 . . 111.67(10) yes
    N1 C2 C1 . . 108.02(9) yes
    N1 C2 C3 . . 111.94(9) yes
    C1 C2 C3 . . 107.85(9) yes
    N1 C2 H2 . . 109.7 ?
    C1 C2 H2 . . 109.7 ?
    C3 C2 H2 . . 109.7 ?
    C4 C3 C2 . . 114.55(9) yes
    C4 C3 H3A . . 108.6 ?
    C2 C3 H3A . . 108.6 ?
    C4 C3 H3B . . 108.6 ?
    C2 C3 H3B . . 108.6 ?
    H3A C3 H3B . . 107.6 ?
    C5 C4 C3 . . 110.63(10) yes
    C5 C4 H4A . . 109.5 ?
    C3 C4 H4A . . 109.5 ?
    C5 C4 H4B . . 109.5 ?
    C3 C4 H4B . . 109.5 ?
    H4A C4 H4B . . 108.1 ?
    O3 C5 O4 . . 123.93(10) yes
    O3 C5 C4 . . 122.46(10) yes
    O4 C5 C4 . . 113.59(10) yes
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
    O2 C1 C2 N1 . . . . -21.37(15) y
    O1 C1 C2 N1 . . . . 161.21(10) y
    O2 C1 C2 C3 . . . . 99.80(13) ?
    O1 C1 C2 C3 . . . . -77.62(12) ?
    N1 C2 C3 C4 . . . . -69.92(13) ?
    C1 C2 C3 C4 . . . . 171.39(9) ?
    C2 C3 C4 C5 . . . . -171.71(9) ?
    C3 C4 C5 O3 . . . . 14.84(16) ?
    C3 C4 C5 O4 . . . . -166.61(10) ?
    H1C N1 C2 C1 . . . . -60.0 y
    H1B N1 C2 C1 . . . . 60.0 y
    H1A N1 C2 C1 . . . . -180.0 y
    H1 O1 C1 C2 . . . . 179.8 y
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
    N1 H1A Cl1 . 0.91 2.29 3.1406(10) 156.5 yes
    N1 H1B Cl1 1_455 0.91 2.34 3.1890(10) 155.0 yes
    N1 H1C O2 4_565 0.91 2.04 2.8700(13) 150.9 yes
    O1 H1 O3 2_564 0.84 1.79 2.6208(13) 170.3 yes
    O4 H4 Cl1 4_466 0.84 2.21 3.0389(9) 168.4 yes
