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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                                                              #
#                                                                            #
#            Copyright International Union of Crystallography                #
#                                                                            #
##############################################################################
                                             
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
(R)-1,3-Thiazolidin-3-ium-4-carboxylate
;
_chemical_name_common     'R-thioproline'
_chemical_formula_moiety     'C4 H7 N O2 S'
_chemical_formula_sum     'C4 H7 N O2 S'
_chemical_formula_iupac     'C4 H7 N O2 S'
_chemical_formula_weight     133.18
_chemical_melting_point     ?
_symmetry_cell_setting     orthorhombic
_symmetry_space_group_name_H-M     'P 21 21 21'
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     5.6733(3)
_cell_length_b     9.9375(6)
_cell_length_c     9.9407(6)
_cell_angle_alpha     90.00
_cell_angle_beta     90.00
_cell_angle_gamma     90.00
_cell_volume     560.44(6)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     2816
_cell_measurement_theta_min     2.90
_cell_measurement_theta_max     29.99
_cell_measurement_temperature     293(2)
_exptl_crystal_description     'block'
_exptl_crystal_colour     'colourless'
_exptl_crystal_size_max      .52
_exptl_crystal_size_mid      .20
_exptl_crystal_size_min      .20
_exptl_crystal_density_diffrn     1.578
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     280
_exptl_absorpt_coefficient_mu      .476
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS, Bruker, 1999)'
_exptl_absorpt_correction_T_min      .875
_exptl_absorpt_correction_T_max      .920
_exptl_special_details
;
 ?
;
_diffrn_ambient_temperature     293(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength      .71073
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Bruker SMART1000 CCD'
_diffrn_measurement_method     ω
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     4858
_diffrn_reflns_av_R_equivalents      .0266
_diffrn_reflns_av_sigmaI/netI      .0248
_diffrn_reflns_theta_min     2.90
_diffrn_reflns_theta_max     29.98
_diffrn_reflns_theta_full     29.98
_diffrn_measured_fraction_theta_max     1.000
_diffrn_measured_fraction_theta_full     1.000
_diffrn_reflns_limit_h_min     -7
_diffrn_reflns_limit_h_max     5
_diffrn_reflns_limit_k_min     -12
_diffrn_reflns_limit_k_max     13
_diffrn_reflns_limit_l_min     -13
_diffrn_reflns_limit_l_max     13
_diffrn_standards_number     ?
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     ?
_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     1611
_reflns_number_gt     1483
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all      .032
_refine_ls_R_factor_gt      .029
_refine_ls_wR_factor_ref      .079
_refine_ls_goodness_of_fit_ref     1.028
_refine_ls_restrained_S_all     1.028
_refine_ls_number_reflns     1611
_refine_ls_number_parameters     73
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
               'calc w=1/[σ²(Fo²)+(0.053P)²P] where P = (Fo²+2Fc²)/3'
_refine_ls_shift/su_max     <0.001
_refine_ls_shift/su_mean      .000
_refine_diff_density_max      .283
_refine_diff_density_min      -.228
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
_refine_ls_abs_structure_details     '(Flack, 1983)'
_refine_ls_abs_structure_Flack      .07(8)
loop_
    _atom_type_symbol
    _atom_type_description
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
    'C' 'C'  .0033  .0016
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'H' 'H'  .0000  .0000
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'N' 'N'  .0061  .0033
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'O' 'O'  .0106  .0060
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'S' 'S'  .1246  .1234
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'SMART (Bruker, 1999)'
_computing_cell_refinement     'SMART'
_computing_data_reduction     'SMART'
_computing_structure_solution     'SHELXS97 (Sheldrick, 1997)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 1997)'
_computing_molecular_graphics     'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material     'SHELXL97'
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
    S1  .10887(7)  .17235(4)  .38298(4)  .03733(12) Uani d . 1 . . S
    O1  -.27669(19)  -.00443(12)  .11609(14)  .0360(2) Uani d . 1 . . O
    N1  .3165(2)  .12326(12)  .15031(11)  .0250(2) Uani d . 1 . . N
    H1A  .4381  .0932  .1251  .030 Uiso d R 1 . . H
    H1B  .2707  .1723  .0909  .030 Uiso d R 1 . . H
    O2  -.0738(2)  .15571(15)  .00960(14)  .0487(3) Uani d . 1 . . O
    C1  -.0948(2)  .06210(14)  .09099(13)  .0258(3) Uani d . 1 . . C
    C2  .1292(2)  .01851(13)  .16804(12)  .0225(2) Uani d . 1 . . C
    H2  .1858  -.0671  .1311  .027 Uiso calc R 1 . . H
    C3  .0883(3)  .00246(16)  .31848(14)  .0319(3) Uani d . 1 . . C
    H3A  .2077  -.0549  .3585  .038 Uiso calc R 1 . . H
    H3B  -.0659  -.0357  .3363  .038 Uiso calc R 1 . . H
    C4  .3628(3)  .19746(15)  .27834(15)  .0337(3) Uani d . 1 . . C
    H4A  .3858  .2925  .2605  .040 Uiso calc R 1 . . H
    H4B  .5030  .1626  .3220  .040 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
    S1  .0374(2)  .0440(2)  .03060(16)  .00468(17)  .00258(16)  -.00600(16)
    O1  .0193(5)  .0357(5)  .0532(6)  -.0010(4)  -.0035(5)  .0079(6)
    N1  .0179(5)  .0280(5)  .0292(5)  .0000(4)  -.0001(4)  .0043(5)
    O2  .0316(6)  .0568(8)  .0575(7)  -.0026(6)  -.0126(5)  .0315(7)
    C1  .0198(6)  .0278(6)  .0299(6)  .0032(5)  -.0016(5)  .0006(5)
    C2  .0173(5)  .0221(5)  .0279(5)  .0015(5)  .0000(5)  .0014(5)
    C3  .0329(8)  .0331(7)  .0296(6)  -.0033(6)  -.0022(6)  .0100(5)
    C4  .0305(7)  .0321(7)  .0386(7)  -.0048(6)  -.0020(6)  -.0056(6)
_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
    S1 C4 . 1.7945(16) yes
    S1 C3 . 1.8097(17) yes
    O1 C1 . 1.2509(18) yes
    N1 C4 . 1.4942(18) yes
    N1 C2 . 1.4978(17) yes
    N1 H1A .  .7924 ?
    N1 H1B .  .8087 ?
    O2 C1 . 1.2386(18) yes
    C1 C2 . 1.5457(18) yes
    C2 C3 . 1.5217(19) yes
    C2 H2 .  .9800 ?
    C3 H3A .  .9700 ?
    C3 H3B .  .9700 ?
    C4 H4A .  .9700 ?
    C4 H4B .  .9700 ?
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
    C4 S1 C3 . . 88.62(7) yes
    C4 N1 C2 . . 111.56(10) yes
    C4 N1 H1A . . 107.6 ?
    C2 N1 H1A . . 113.1 ?
    C4 N1 H1B . . 112.4 ?
    C2 N1 H1B . . 106.1 ?
    H1A N1 H1B . . 106.0 ?
    O2 C1 O1 . . 127.34(13) yes
    O2 C1 C2 . . 117.08(12) yes
    O1 C1 C2 . . 115.56(12) yes
    N1 C2 C3 . . 107.25(11) yes
    N1 C2 C1 . . 109.28(10) yes
    C3 C2 C1 . . 113.02(12) yes
    N1 C2 H2 . . 109.1 ?
    C3 C2 H2 . . 109.1 ?
    C1 C2 H2 . . 109.1 ?
    C2 C3 S1 . . 103.92(9) yes
    C2 C3 H3A . . 111.0 ?
    S1 C3 H3A . . 111.0 ?
    C2 C3 H3B . . 111.0 ?
    S1 C3 H3B . . 111.0 ?
    H3A C3 H3B . . 109.0 ?
    N1 C4 S1 . . 106.49(9) yes
    N1 C4 H4A . . 110.4 ?
    S1 C4 H4A . . 110.4 ?
    N1 C4 H4B . . 110.4 ?
    S1 C4 H4B . . 110.4 ?
    H4A C4 H4B . . 108.6 ?
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 . . . . 13.51(18) no
    O2 C1 C2 C3 . . . . 132.85(15) no
    O1 C1 C2 N1 . . . . -168.24(12) no
    O1 C1 C2 N1 . . . . -168.24(12) no
    C2 N1 C4 S1 . . . . -19.86(13) no
    N1 C4 S1 C3 . . . . 36.89(10) no
    C4 S1 C3 C2 . . . . -43.76(11) no
    S1 C3 C2 N1 . . . . 38.68(13) no
    C3 C2 N1 C4 . . . . -12.38(15) no
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 O1 1_655  .79 1.89 2.6556(16) 162.6 yes
    N1 H1B O2 .  .81 2.12 2.6389(16) 121.8 yes
    N1 H1B O2 4  .81 2.17 2.7819(16) 132.9 yes
data_neil
_journal_date_recd_electronic     2001-05-10
_journal_date_accepted     2001-06-29
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2001
_journal_volume     57
_journal_issue      8
_journal_page_first     o697
_journal_page_last     o699
_journal_paper_category     EO
_publ_contact_author
;
William T. A. Harrison
Department of Chemistry
University of Aberdeen
Aberdeen
AB24 3UE
;
_publ_contact_author_email     w.harrison@abdn.ac.uk
_publ_contact_author_fax     ' 44 1224 272921 '
_publ_contact_author_phone     ' 44 1224 272897 '
_publ_section_title
;
(R)-1,3-Thiazolidin-3-ium-4-carboxylate
;
loop_
    _publ_author_name
    _publ_author_address
    'Grant, Neil'
;
Department of Chemistry,
University of Aberdeen,
Aberdeen AB24 3UE
Scotland
;
    'Ward, Mark F.'
;
Department of Chemistry,
University of Aberdeen,
Aberdeen AB24 3UE
Scotland
;
    'Jaspars, Marcel'
;
Department of Chemistry,
University of Aberdeen,
Aberdeen AB24 3UE
Scotland
;
    'Harrison, William T. A.'
;
Department of Chemistry,
University of Aberdeen,
Aberdeen AB24 3UE
Scotland
;
