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In the title compound, C4H6N2O2S.·3H2O, the 2-amino-2-thia­zoline-4-carboxyl­ic acid mol­ecule is in a zwitterionic form and shows amino–imino tautomerism. There are intermolecular O—H...O, O—H...N, N—H...O and C—H...O interactions, forming a three-dimensional network.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803022360/ob6301sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536803022360/ob6301Isup2.hkl
Contains datablock I

CCDC reference: 226976

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.023
  • wR factor = 0.082
  • Data-to-parameter ratio = 13.5

checkCIF/PLATON results

No syntax errors found



Alert level C STRVA01_ALERT_4_C Flack test results are ambiguous. From the CIF: _refine_ls_abs_structure_Flack 0.490 From the CIF: _refine_ls_abs_structure_Flack_su 0.090 PLAT033_ALERT_2_C Flack Parameter Value Deviates from Zero ....... 0.49 PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT128_ALERT_4_C Non-standard setting of Space group Pca21 .... P21ab PLAT250_ALERT_2_C Large U3/U1 ratio for average U(i,j) tensor .... 2.10 PLAT731_ALERT_1_C Bond Calc 0.83(4), Rep 0.825(19) ...... 2.11 su-Rat O5 -H5A 1.555 1.555 PLAT731_ALERT_1_C Bond Calc 0.86(4), Rep 0.854(19) ...... 2.11 su-Rat O5 -H5B 1.555 1.555 PLAT735_ALERT_1_C D-H Calc 0.83(4), Rep 0.825(19) ...... 2.11 su-Rat O5 -H5A 1.555 1.555 PLAT735_ALERT_1_C D-H Calc 0.86(4), Rep 0.854(19) ...... 2.11 su-Rat O5 -H5B 1.555 1.555 PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 2 H2 O PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 3 H2 O
Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 27.42 From the CIF: _reflns_number_total 1968 Count of symmetry unique reflns 1116 Completeness (_total/calc) 176.34% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 852 Fraction of Friedel pairs measured 0.763 Are heavy atom types Z>Si present yes
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 11 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 5 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 2 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 5 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC & Rigaku, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

(I) top
Crystal data top
C4H6N2O2S·3H2OF(000) = 424
Mr = 200.22Dx = 1.466 Mg m3
Orthorhombic, P21abMo Kα radiation, λ = 0.71073 Å
Hall symbol: P -2b 2aCell parameters from 11305 reflections
a = 8.0835 (4) Åθ = 2.5–27.4°
b = 8.1546 (3) ŵ = 0.35 mm1
c = 13.7591 (7) ÅT = 293 K
V = 906.97 (7) Å3Prism, colorless
Z = 40.3 × 0.29 × 0.25 mm
Data collection top
Rigaku R-AXIS RAPID
diffractometer
1620 reflections with I > 2σ(I)
Detector resolution: 10.00 pixels mm-1Rint = 0.019
ω scansθmax = 27.4°, θmin = 1.5°
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)
h = 1010
Tmin = 0.849, Tmax = 0.917k = 1010
8161 measured reflectionsl = 1717
1968 independent reflections
Refinement top
Refinement on F2 w = 1/[σ2(Fo2) + (0.0444P)2]
where P = (Fo2 + 2Fc2)/3
Least-squares matrix: full(Δ/σ)max = 0.004
R[F2 > 2σ(F2)] = 0.023Δρmax = 0.23 e Å3
wR(F2) = 0.082Δρmin = 0.15 e Å3
S = 1.07Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
1968 reflectionsExtinction coefficient: 0.010 (2)
146 parametersAbsolute structure: Flack (1983), 852 Friedel pairs
10 restraintsAbsolute structure parameter: 0.49 (9)
H atoms treated by a mixture of independent and constrained refinement
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S0.34336 (8)0.21566 (6)0.19887 (4)0.03618 (16)
O10.3635 (3)0.21679 (19)0.40829 (12)0.0473 (5)
O20.4055 (2)0.3504 (2)0.27003 (13)0.0470 (5)
O30.1931 (2)0.4669 (2)0.49423 (13)0.0380 (4)
O40.4469 (3)0.3793 (3)0.07247 (15)0.0505 (5)
O50.1440 (3)0.1299 (3)0.0036 (2)0.0716 (7)
N10.4909 (3)0.0671 (2)0.33846 (14)0.0306 (4)
N20.4767 (3)0.3507 (2)0.35625 (15)0.0389 (5)
C10.3293 (4)0.0063 (2)0.20038 (17)0.0392 (6)
C20.4635 (3)0.0667 (2)0.27056 (15)0.0296 (4)
C30.4474 (3)0.2142 (3)0.30938 (15)0.0289 (4)
C40.4062 (3)0.2241 (3)0.32158 (17)0.0315 (5)
H10.558 (3)0.042 (4)0.3836 (17)0.043 (8)*
H1A0.22080.04080.22250.047*
H1B0.34780.05030.13580.047*
H20.56560.08860.23440.036*
H2A0.443 (4)0.439 (3)0.327 (2)0.055 (9)*
H2B0.540 (3)0.350 (4)0.4061 (16)0.044 (8)*
H3A0.259 (4)0.532 (4)0.522 (2)0.064 (10)*
H3B0.255 (4)0.400 (3)0.468 (2)0.055 (10)*
H4A0.348 (3)0.388 (4)0.051 (2)0.067 (10)*
H4B0.430 (5)0.378 (4)0.1326 (14)0.073 (12)*
H5A0.082 (5)0.055 (4)0.021 (3)0.087 (15)*
H5B0.077 (5)0.202 (4)0.019 (3)0.090 (15)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S0.0455 (3)0.0275 (2)0.0356 (3)0.0026 (3)0.0055 (3)0.0069 (2)
O10.0738 (14)0.0288 (7)0.0391 (8)0.0096 (10)0.0119 (10)0.0007 (7)
O20.0803 (15)0.0219 (7)0.0387 (9)0.0001 (8)0.0030 (9)0.0025 (7)
O30.0413 (10)0.0346 (9)0.0380 (9)0.0022 (8)0.0034 (8)0.0038 (8)
O40.0499 (13)0.0585 (12)0.0432 (11)0.0009 (11)0.0019 (10)0.0039 (9)
O50.0502 (13)0.0704 (17)0.0941 (19)0.0039 (13)0.0108 (12)0.0261 (15)
N10.0382 (11)0.0220 (8)0.0317 (9)0.0008 (9)0.0060 (9)0.0030 (7)
N20.0545 (14)0.0239 (9)0.0383 (12)0.0005 (10)0.0063 (10)0.0022 (9)
C10.0561 (16)0.0252 (9)0.0362 (11)0.0003 (14)0.0084 (13)0.0016 (9)
C20.0364 (11)0.0217 (9)0.0307 (10)0.0009 (9)0.0025 (10)0.0010 (8)
C30.0309 (11)0.0255 (10)0.0303 (11)0.0000 (9)0.0034 (9)0.0017 (9)
C40.0379 (12)0.0225 (9)0.0341 (12)0.0012 (9)0.0026 (9)0.0024 (9)
Geometric parameters (Å, º) top
S—C31.738 (2)N1—H10.848 (17)
S—C11.814 (2)N2—H2A0.867 (18)
O1—C41.243 (3)N2—H2B0.856 (17)
O3—H3A0.846 (18)C1—C21.533 (4)
O3—H3B0.821 (18)C1—H1A0.97
O4—H4A0.855 (19)C1—H1B0.97
O4—H4B0.839 (18)C2—H20.98
O5—H5A0.825 (19)C3—N21.308 (3)
O5—H5B0.854 (19)C4—O21.250 (3)
N1—C31.313 (3)C4—C21.534 (3)
N1—C21.454 (3)
S—C1—H1A110.4C2—C1—S106.47 (17)
S—C1—H1B110.4C2—C1—H1A110.4
O1—C4—O2125.6 (2)C2—C1—H1B110.4
O1—C4—C2118.88 (19)C3—S—C190.77 (11)
O2—C4—C2115.5 (2)C3—N1—C2116.70 (19)
N1—C2—C1105.76 (17)C3—N1—H1128 (2)
N1—C2—C4112.33 (18)C3—N2—H2A115 (2)
N1—C3—S113.74 (16)C3—N2—H2B120 (2)
N1—C2—H2109.5C4—C2—H2109.5
N2—C3—N1125.4 (2)H1A—C1—H1B108.6
N2—C3—S120.88 (17)H2A—N2—H2B124 (3)
C1—C2—C4110.1 (2)H3A—O3—H3B103 (3)
C1—C2—H2109.5H5A—O5—H5B103 (4)
C2—N1—H1113 (2)H4A—O4—H4B101 (4)
S—C1—C2—N126.2 (2)C1—S—C3—N18.9 (2)
S—C1—C2—C4147.72 (17)C2—N1—C3—N2173.2 (2)
O1—C4—C2—N111.6 (3)C2—N1—C3—S6.7 (3)
O1—C4—C2—C1106.0 (3)C3—S—C1—C220.29 (19)
O2—C4—C2—N1169.1 (2)C3—N1—C2—C122.0 (3)
O2—C4—C2—C173.3 (3)C3—N1—C2—C4142.1 (2)
C1—S—C3—N2171.2 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O5—H5A···O4i0.83 (2)1.94 (2)2.759 (3)175 (4)
O5—H5B···O4ii0.85 (2)1.94 (2)2.787 (3)174 (4)
O4—H4B···O20.84 (2)1.92 (2)2.749 (3)173 (4)
O3—H3A···O1iii0.85 (2)1.97 (2)2.802 (3)166 (4)
O3—H3B···O10.82 (2)1.92 (2)2.731 (3)169 (3)
O3—H3A···N1iii0.85 (2)2.80 (3)3.343 (3)123 (3)
N1—H1···O3iv0.85 (2)1.97 (2)2.816 (3)173 (3)
N2—H2A···O2v0.87 (2)1.91 (2)2.772 (3)170 (3)
N2—H2B···O1vi0.86 (2)2.98 (3)3.411 (3)114 (2)
N2—H2B···O3vii0.86 (2)2.08 (2)2.862 (3)152 (3)
C1—H1B···O50.972.863.288 (4)108
C1—H1B···O40.972.933.640 (3)131
C1—H1A···O2i0.972.783.744 (4)175
C2—H2···O2iv0.982.843.637 (3)140
Symmetry codes: (i) x1/2, y1/2, z; (ii) x1/2, y, z; (iii) x, y1/2, z+1; (iv) x+1/2, y1/2, z; (v) x, y+1, z; (vi) x, y+1/2, z+1; (vii) x+1/2, y, z+1.
 

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