4-(4-Oxopent-2-en-2-yl-amino)-1,2,4-triazol-1-ium-5-thiol-ate.

In the title compound, C(8)H(12)N(4)OS, an intra-molecular N-H⋯O hydrogen bond links the imine N atom to the oxo O atom. In the crystal, mol-ecules are linked by inter-molecular N-H⋯O and N-H⋯S hydrogen bonds, forming a two-dimensional framework.

Related literature

For Schiff base metal complexes, see: Lacroix (2001 ▶); Sabater et al. (2001 ▶). For the use of 1,2,4-triazole and its derivatives as ligands to bridge metal ions, see: Yi et al. (2004 ▶).

Experimental

Crystal data

C8H12N4OS

M = 212.28

Monoclinic,

a = 10.620 (6) Å

b = 9.520 (5) Å

c = 10.764 (5) Å

β = 99.560 (14)°

V = 1073.2 (10) Å3

Z = 4

Mo Kα radiation

μ = 0.28 mm−1

T = 293 K

0.26 × 0.23 × 0.18 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.932, T max = 0.952

9199 measured reflections

2071 independent reflections

1688 reflections with I > 2σ(I)

R int = 0.030

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.105

S = 1.06

2071 reflections

130 parameters

H-atom parameters constrained

Δρmax = 0.24 e Å−3

Δρmin = −0.22 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809019850/at2792sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809019850/at2792Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C8H12N4OS	F(000) = 448
Mr = 212.28	Dx = 1.314 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 9199 reflections
a = 10.620 (6) Å	θ = 2.5–26.0°
b = 9.520 (5) Å	µ = 0.28 mm−1
c = 10.764 (5) Å	T = 293 K
β = 99.560 (14)°	Prism, yellow
V = 1073.2 (10) Å3	0.26 × 0.23 × 0.18 mm
Z = 4

Bruker SMART APEXII CCD area-detector diffractometer	2071 independent reflections
Radiation source: fine-focus sealed tube	1688 reflections with I > 2σ(I)
graphite	Rint = 0.030
φ and ω scans	θmax = 26.0°, θmin = 2.5°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −12→13
Tmin = 0.932, Tmax = 0.952	k = −11→11
9199 measured reflections	l = −13→13

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.105	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.0494P)2 + 0.3337P] where P = (Fo2 + 2Fc2)/3
2071 reflections	(Δ/σ)max < 0.001
130 parameters	Δρmax = 0.24 e Å−3
0 restraints	Δρmin = −0.22 e Å−3

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.

	x	y	z	Uiso*/Ueq
C1	0.6978 (2)	0.4476 (2)	0.6177 (2)	0.0581 (6)
H1A	0.6385	0.4804	0.6695	0.087*
H1B	0.7230	0.5246	0.5697	0.087*
H1C	0.7717	0.4092	0.6702	0.087*
C2	0.63580 (17)	0.3365 (2)	0.53014 (16)	0.0413 (4)
C3	0.51805 (18)	0.2824 (2)	0.53712 (17)	0.0474 (5)
H3	0.4781	0.3133	0.6027	0.057*
C4	0.45166 (17)	0.1828 (2)	0.45229 (17)	0.0437 (4)
C5	0.31956 (19)	0.1390 (3)	0.4704 (2)	0.0598 (6)
H5A	0.2574	0.1966	0.4191	0.090*
H5B	0.3113	0.1500	0.5573	0.090*
H5C	0.3058	0.0423	0.4464	0.090*
C6	0.9660 (2)	0.1873 (2)	0.5572 (2)	0.0579 (5)
H6A	1.0551	0.1644	0.5677	0.087*
H6B	0.9162	0.1048	0.5318	0.087*
H6C	0.9457	0.2212	0.6355	0.087*
C7	0.93642 (17)	0.29676 (19)	0.45994 (16)	0.0420 (4)
C8	0.81958 (17)	0.45095 (18)	0.33090 (15)	0.0377 (4)
N1	0.70361 (13)	0.28695 (16)	0.44362 (13)	0.0430 (4)
H1	0.6761	0.2136	0.4010	0.052*
N2	0.81498 (13)	0.34888 (15)	0.42069 (13)	0.0381 (3)
N3	0.94393 (14)	0.45391 (16)	0.32250 (14)	0.0445 (4)
H3A	0.9753	0.5092	0.2723	0.053*
N4	1.01765 (14)	0.35996 (17)	0.40183 (15)	0.0483 (4)
O1	0.49708 (12)	0.13376 (15)	0.36199 (13)	0.0536 (4)
S1	0.69902 (5)	0.54628 (5)	0.25545 (4)	0.04948 (19)

	U11	U22	U33	U12	U13	U23
C1	0.0537 (13)	0.0681 (14)	0.0536 (11)	−0.0014 (10)	0.0118 (10)	−0.0165 (10)
C2	0.0402 (10)	0.0460 (10)	0.0389 (9)	0.0044 (8)	0.0103 (8)	0.0013 (7)
C3	0.0418 (11)	0.0602 (12)	0.0439 (10)	0.0030 (9)	0.0180 (8)	−0.0033 (9)
C4	0.0370 (10)	0.0495 (11)	0.0474 (10)	0.0029 (8)	0.0151 (8)	0.0062 (8)
C5	0.0426 (12)	0.0754 (15)	0.0653 (13)	−0.0085 (10)	0.0198 (10)	0.0014 (11)
C6	0.0566 (13)	0.0560 (12)	0.0597 (12)	0.0071 (10)	0.0055 (10)	0.0110 (10)
C7	0.0369 (10)	0.0440 (10)	0.0447 (9)	0.0003 (8)	0.0055 (8)	−0.0035 (8)
C8	0.0379 (10)	0.0402 (9)	0.0360 (8)	−0.0018 (7)	0.0089 (7)	−0.0040 (7)
N1	0.0388 (9)	0.0446 (9)	0.0490 (8)	−0.0086 (7)	0.0175 (7)	−0.0082 (7)
N2	0.0316 (8)	0.0411 (8)	0.0427 (8)	−0.0030 (6)	0.0092 (6)	−0.0012 (6)
N3	0.0359 (9)	0.0500 (9)	0.0493 (9)	−0.0028 (7)	0.0116 (7)	0.0062 (7)
N4	0.0339 (8)	0.0570 (10)	0.0536 (9)	0.0008 (7)	0.0059 (7)	0.0037 (7)
O1	0.0461 (8)	0.0604 (9)	0.0591 (8)	−0.0084 (6)	0.0223 (7)	−0.0143 (7)
S1	0.0430 (3)	0.0588 (3)	0.0476 (3)	0.0104 (2)	0.0103 (2)	0.0053 (2)

C1—C2	1.495 (3)	C6—C7	1.474 (3)
C1—H1A	0.9600	C6—H6A	0.9600
C1—H1B	0.9600	C6—H6B	0.9600
C1—H1C	0.9600	C6—H6C	0.9600
C2—N1	1.353 (2)	C7—N4	1.295 (2)
C2—C3	1.366 (3)	C7—N2	1.381 (2)
C3—C4	1.420 (3)	C8—N3	1.339 (2)
C3—H3	0.9300	C8—N2	1.377 (2)
C4—O1	1.245 (2)	C8—S1	1.6664 (19)
C4—C5	1.507 (3)	N1—N2	1.380 (2)
C5—H5A	0.9600	N1—H1	0.8600
C5—H5B	0.9600	N3—N4	1.386 (2)
C5—H5C	0.9600	N3—H3A	0.8600
C2—C1—H1A	109.5	C7—C6—H6B	109.5
C2—C1—H1B	109.5	H6A—C6—H6B	109.5
H1A—C1—H1B	109.5	C7—C6—H6C	109.5
C2—C1—H1C	109.5	H6A—C6—H6C	109.5
H1A—C1—H1C	109.5	H6B—C6—H6C	109.5
H1B—C1—H1C	109.5	N4—C7—N2	110.40 (16)
N1—C2—C3	120.20 (17)	N4—C7—C6	126.26 (17)
N1—C2—C1	116.86 (17)	N2—C7—C6	123.32 (16)
C3—C2—C1	122.92 (17)	N3—C8—N2	102.27 (15)
C2—C3—C4	125.30 (16)	N3—C8—S1	129.95 (14)
C2—C3—H3	117.4	N2—C8—S1	127.77 (14)
C4—C3—H3	117.4	C2—N1—N2	122.95 (15)
O1—C4—C3	122.48 (17)	C2—N1—H1	118.5
O1—C4—C5	119.12 (18)	N2—N1—H1	118.5
C3—C4—C5	118.38 (17)	C8—N2—N1	123.94 (14)
C4—C5—H5A	109.5	C8—N2—C7	109.16 (14)
C4—C5—H5B	109.5	N1—N2—C7	125.19 (15)
H5A—C5—H5B	109.5	C8—N3—N4	114.05 (15)
C4—C5—H5C	109.5	C8—N3—H3A	123.0
H5A—C5—H5C	109.5	N4—N3—H3A	123.0
H5B—C5—H5C	109.5	C7—N4—N3	104.12 (15)
C7—C6—H6A	109.5
N1—C2—C3—C4	−5.7 (3)	C2—N1—N2—C7	105.0 (2)
C1—C2—C3—C4	176.25 (19)	N4—C7—N2—C8	0.6 (2)
C2—C3—C4—O1	0.7 (3)	C6—C7—N2—C8	179.02 (17)
C2—C3—C4—C5	−177.3 (2)	N4—C7—N2—N1	166.12 (16)
C3—C2—N1—N2	171.33 (16)	C6—C7—N2—N1	−15.5 (3)
C1—C2—N1—N2	−10.5 (3)	N2—C8—N3—N4	−0.11 (19)
N3—C8—N2—N1	−166.02 (14)	S1—C8—N3—N4	179.01 (13)
S1—C8—N2—N1	14.8 (2)	N2—C7—N4—N3	−0.62 (19)
N3—C8—N2—C7	−0.27 (18)	C6—C7—N4—N3	−178.99 (18)
S1—C8—N2—C7	−179.42 (13)	C8—N3—N4—C7	0.5 (2)
C2—N1—N2—C8	−91.5 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1	0.86	2.03	2.659 (2)	130
N1—H1···S1i	0.86	2.81	3.4127 (19)	129
N3—H3A···O1ii	0.86	1.93	2.772 (2)	166

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1	0.86	2.03	2.659 (2)	130
N1—H1⋯S1i	0.86	2.81	3.4127 (19)	129
N3—H3A⋯O1ii	0.86	1.93	2.772 (2)	166

Symmetry codes: (i) ; (ii) .