2-(3-Methyl-5-thioxo-4,5-dihydro-1H-1,2,4-triazol-4-yl)acetic acid

All inter­atomic distances in the title compound, C₅H₇N₃O₂S, are normal. The 1,2,4-triazoline ring is planar and it is inclined at 78.61 (7)° to the planar acetic acid group. The mol­ecules of the title compound are connected via O—H...N hydrogen bonds into zigzag chains along the [101] direction and by N—H...S hydrogen bonds into a three-dimensional net. In addition, a weak C—H...O hydrogen bond can also be found in the structure.

Key indicators

• Single-crystal X-ray study
• T = 291 K
• Mean [sigma](C-C)= 0.003 Å
• R factor = 0.034
• wR factor = 0.087
• Data-to-parameter ratio = 13.3

checkCIF/PLATON results

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S1. Comment

The title compound, (I), is a member of 1,2,4-triazoline-3-thione derivatives family, known to posses antibacterial, anitimycotical and antivirostatical activity (Veverka and Marchalin, 1987; Bohn and Karow, 1981; Potts, 1961; Santus, 1980).

All interatomic distances in (I) are normal. The 1,2,4-triazoline ring of (I) can be considered as planar in the range of experimental error. The most deviating N1 atom derives 0.0046 (13) Å from weighted least squares plane of the ring. The C3, C5, S1 atoms deviate respectively 0.082 (3), -0.004 (4), -0.049 (3) Å from this plane. The acetic acid moiety is planar (Table 1) and the most deviating atom is C4 [0.0005 (17) Å] from the weighted O1/O2/C3/C4 least-squares plane. The N3 atom deviates 0.106 (4) Å from this plane. The above mentioned weighted least-squares planes are inclined at 78.61 (7)°.

The molecules of (I) are connected via O1—H1O···N2 hydrogen bonds (Table 1, C₁¹(7) motif (Bernstein et al., 1995)) to zigzag chains extended along the [101] axis. The N1—H1N···S1 hydrogen bonds (Table 1, R₂²(8) motif) expands the chains to a folded three dimensional sheet in the (-101) plane. In (I) can be found also one C—H···O short contact (Table 1), which, according to Desiraju and Steiner (1999), can be classified as weak hydrogen bond (C₁¹(4) motif).

Related literature

For potential applications, see: Bohn & Karow (1981); Potts (1961); Santus (1980). For general synthesis procedures, see: Bany & Dobosz (1972); Veverka & Marchalin (1987).

For related literature, see: Bernstein et al. (1995); Desiraju & Steiner (1999).

S2. Experimental

The title compound was synthesized according to method of Veverka and Marchalin (1987). Crystals were obtained by crystallization from mixture of water, methanol, ethanol and 2-butanone (3:1:5:1).

S3. Refinement

The hydrogen atoms were placed in calculated positions after four cycles of anisotrophic refinement and were refined as riding on the parent atom with U_iso(H) = 1.2U_eq(C-non-methyl or N) and U_iso(H) = 1.5U_eq(C-methyl or O). The methyl and hydroxyl group was allowed to rotate about its local threefold axis (AFIX 137 and 147 respectively).

Computing details

Data collection: KM-4 Software (Kuma, 1993); cell refinement: KM-4 Software (Kuma, 1993); data reduction: DATAPROC (Gałdecki et al., 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP in SHELXTL/PC (Sheldrick, 1990b) and ORTEP-3 for Windows (Version 1.062; Farrugia, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997) and PLATON (Spek, 2003).

Figures

	Fig. 1. Molecular structure of the title compound (I). Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. A part of the molecular packing of the title compound. Hydrogen bonds are indicated by dashed lines.

2-(3-Methyl-5-thioxo-4,5-dihydro-1H-1,2,4-triazol-4-yl)acetic acid

Crystal data

C5H7N3O2S	F(000) = 360
Mr = 173.20	Dx = 1.517 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 99 reflections
a = 5.1706 (3) Å	θ = 2–20°
b = 9.4818 (6) Å	µ = 0.38 mm^−1
c = 15.6763 (9) Å	T = 291 K
β = 99.250 (5)°	Needle, colourless
V = 758.56 (8) Å^3	0.22 × 0.07 × 0.07 mm
Z = 4

Data collection

Kuma KM-4 diffractometer	1108 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.000
Graphite monochromator	θmax = 25.1°, θmin = 3.4°
ω–2θ scans	h = −6→6
Absorption correction: numerical (X-RED; Stoe & Cie, 1999)	k = 0→11
Tmin = 0.918, Tmax = 0.983	l = 0→18
1354 measured reflections	3 standard reflections every 100 reflections
1354 independent reflections	intensity decay: 2.1%

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: structure-invariant direct methods
R[F^2 > 2σ(F^2)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.087	H-atom parameters constrained
S = 1.09	w = 1/[σ^2(Fo^2) + (0.0468P)^2] where P = (Fo^2 + 2Fc^2)/3
1354 reflections	(Δ/σ)max < 0.001
102 parameters	Δρmax = 0.16 e Å^−3
0 restraints	Δρmin = −0.24 e Å^−3

Special details

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.

Refinement. 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 > σ(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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
S1	0.99527 (11)	1.04539 (6)	0.63708 (3)	0.0393 (2)
O1	0.7717 (3)	0.88549 (17)	0.88096 (9)	0.0437 (4)
H1O	0.8832	0.8517	0.9185	0.066*
C4	0.8051 (4)	0.8362 (2)	0.80424 (12)	0.0301 (5)
O2	0.9822 (3)	0.76167 (17)	0.79093 (9)	0.0420 (4)
N1	0.7338 (3)	0.8532 (2)	0.52587 (10)	0.0401 (5)
H1N	0.8106	0.8759	0.4831	0.048*
N3	0.6155 (3)	0.84909 (19)	0.64966 (10)	0.0313 (4)
C3	0.5851 (4)	0.8886 (2)	0.73708 (12)	0.0336 (5)
H3A	0.4208	0.8508	0.7495	0.040*
H3B	0.5763	0.9905	0.7407	0.040*
C2	0.7812 (4)	0.9166 (2)	0.60293 (12)	0.0335 (5)
N2	0.5497 (4)	0.7480 (2)	0.52213 (11)	0.0413 (5)
C1	0.4797 (4)	0.7476 (2)	0.59811 (12)	0.0347 (5)
C5	0.2828 (4)	0.6513 (3)	0.62525 (15)	0.0438 (6)
H5A	0.2063	0.5947	0.5769	0.066*
H5B	0.1484	0.7056	0.6456	0.066*
H5C	0.3661	0.5911	0.6708	0.066*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0452 (3)	0.0464 (4)	0.0274 (3)	−0.0021 (3)	0.0090 (2)	−0.0016 (2)
O1	0.0578 (10)	0.0515 (10)	0.0206 (8)	0.0089 (8)	0.0029 (7)	−0.0014 (7)
C4	0.0347 (11)	0.0345 (11)	0.0222 (10)	−0.0032 (9)	0.0082 (8)	0.0018 (9)
O2	0.0366 (8)	0.0546 (10)	0.0356 (8)	0.0104 (8)	0.0087 (7)	0.0068 (7)
N1	0.0495 (11)	0.0521 (12)	0.0202 (9)	−0.0065 (10)	0.0095 (8)	0.0007 (8)
N3	0.0322 (9)	0.0425 (10)	0.0198 (8)	0.0043 (8)	0.0065 (7)	0.0005 (8)
C3	0.0347 (11)	0.0459 (13)	0.0212 (10)	0.0065 (10)	0.0073 (8)	−0.0003 (9)
C2	0.0339 (11)	0.0451 (13)	0.0216 (10)	0.0079 (10)	0.0049 (8)	0.0022 (9)
N2	0.0481 (11)	0.0523 (12)	0.0231 (9)	−0.0059 (10)	0.0042 (8)	−0.0024 (8)
C1	0.0366 (11)	0.0445 (13)	0.0220 (10)	0.0046 (10)	0.0015 (8)	0.0012 (9)
C5	0.0442 (13)	0.0501 (14)	0.0375 (13)	−0.0011 (11)	0.0077 (10)	0.0021 (11)

Geometric parameters (Å, º)

S1—C2	1.677 (2)	N3—C1	1.374 (3)
O1—C4	1.327 (2)	N3—C3	1.453 (2)
O1—H1O	0.8200	C3—H3A	0.9700
C4—O2	1.201 (2)	C3—H3B	0.9700
C4—C3	1.505 (3)	N2—C1	1.299 (3)
N1—C2	1.336 (3)	C1—C5	1.480 (3)
N1—N2	1.374 (3)	C5—H5A	0.9600
N1—H1N	0.8600	C5—H5B	0.9600
N3—C2	1.372 (3)	C5—H5C	0.9600
C4—O1—H1O	109.5	H3A—C3—H3B	107.8
O2—C4—O1	125.34 (19)	N1—C2—N3	103.51 (18)
O2—C4—C3	125.76 (18)	N1—C2—S1	129.18 (17)
O1—C4—C3	108.89 (17)	N3—C2—S1	127.30 (15)
C2—N1—N2	112.98 (17)	C1—N2—N1	104.81 (17)
C2—N1—H1N	123.5	N2—C1—N3	110.26 (19)
N2—N1—H1N	123.5	N2—C1—C5	124.8 (2)
C2—N3—C1	108.44 (16)	N3—C1—C5	124.95 (18)
C2—N3—C3	123.71 (18)	C1—C5—H5A	109.5
C1—N3—C3	127.75 (17)	C1—C5—H5B	109.5
N3—C3—C4	112.98 (16)	H5A—C5—H5B	109.5
N3—C3—H3A	109.0	C1—C5—H5C	109.5
C4—C3—H3A	109.0	H5A—C5—H5C	109.5
N3—C3—H3B	109.0	H5B—C5—H5C	109.5
C4—C3—H3B	109.0
N3—C3—C4—O1	175.46 (17)	N3—C3—C4—O2	−4.6 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O···N2^i	0.82	1.96	2.746 (2)	162
N1—H1N···S1^ii	0.86	2.39	3.2499 (18)	176
C3—H3A···O2^iii	0.97	2.60	3.567 (2)	176

Symmetry codes: (i) x+1/2, −y+3/2, z+1/2; (ii) −x+2, −y+2, −z+1; (iii) x−1, y, z.