4-(4-Amino-5-thioxo-4,5-dihydro-1H-1,2,4-triazol-3-yl)pyridinium chloride.

The crystal structure of the title compound, C(7)H(8)N(5)S(+)·Cl(-), is stabilized by inter-molecular N-H⋯Cl and N-H⋯S hydrogen-bond inter-actions.

Related literature

For related literature, see: Jian et al. (2006 ▶); Shi et al. (1995 ▶); Xu et al. (2002 ▶).

Experimental

Crystal data

C7H8N5S+·Cl−

M = 229.69

Monoclinic,

a = 7.6740 (15) Å

b = 13.374 (3) Å

c = 9.965 (2) Å

β = 104.70 (3)°

V = 989.3 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.56 mm−1

T = 293 (2) K

0.20 × 0.15 × 0.11 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

Absorption correction: none

2238 measured reflections

2091 independent reflections

1712 reflections with I > 2σ(I)

R int = 0.050

3 standard reflections every 100 reflections intensity decay: none

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.111

S = 0.96

2091 reflections

135 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.35 e Å−3

Δρmin = −0.29 e Å−3

Data collection: CAD-4 Software (Enraf–Nonius, 1989 ▶); cell refinement: CAD-4 Software; data reduction: NRCVAX (Gabe et al., 1989 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL/PC (Sheldrick, 2008 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808026123/at2609sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808026123/at2609Isup2.hkl

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

C7H8N5S+·Cl–	F000 = 472
Mr = 229.69	Dx = 1.542 Mg m−3
Monoclinic, P21/c	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 25 reflections
a = 7.6740 (15) Å	θ = 4–14º
b = 13.374 (3) Å	µ = 0.56 mm−1
c = 9.965 (2) Å	T = 293 (2) K
β = 104.70 (3)º	Bar, yellow
V = 989.3 (4) Å3	0.20 × 0.15 × 0.11 mm
Z = 4

Enraf–Nonius CAD-4 diffractometer	Rint = 0.050
Radiation source: fine-focus sealed tube	θmax = 27.0º
Monochromator: graphite	θmin = 2.6º
T = 293(2) K	h = 0→9
ω scans	k = 0→15
Absorption correction: none	l = −11→11
2238 measured reflections	3 standard reflections
2091 independent reflections	every 100 reflections
1712 reflections with I > 2σ(I)	intensity decay: none

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.038	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.111	w = 1/[σ2(Fo2) + (0.0626P)2 + 0.6426P] where P = (Fo2 + 2Fc2)/3
S = 0.96	(Δ/σ)max < 0.001
2091 reflections	Δρmax = 0.35 e Å−3
135 parameters	Δρmin = −0.29 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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
Cl1	0.80625 (8)	0.86963 (4)	0.12228 (5)	0.04585 (18)
S1	0.75196 (9)	0.94026 (5)	0.52007 (7)	0.0565 (2)
N1	0.0222 (2)	0.78167 (16)	−0.16338 (19)	0.0469 (5)
H1A	−0.0577	0.7735	−0.2405	0.056*
N2	0.4905 (2)	0.89786 (14)	0.28259 (18)	0.0376 (4)
N3	0.5917 (2)	0.76955 (15)	0.40203 (19)	0.0452 (5)
H3A	0.6505	0.7315	0.4676	0.054*
N4	0.4694 (3)	0.73433 (15)	0.28792 (19)	0.0439 (4)
N5	0.4688 (4)	0.99550 (16)	0.2289 (3)	0.0540 (6)
C1	0.0851 (3)	0.7017 (2)	−0.0868 (2)	0.0494 (6)
H1B	0.0430	0.6383	−0.1173	0.059*
C2	0.2114 (3)	0.71260 (18)	0.0365 (2)	0.0459 (5)
H2A	0.2551	0.6568	0.0903	0.055*
C3	0.2744 (3)	0.80777 (17)	0.0811 (2)	0.0362 (5)
C4	0.2062 (3)	0.88900 (18)	−0.0017 (2)	0.0441 (5)
H4B	0.2462	0.9533	0.0254	0.053*
C5	0.0786 (3)	0.87364 (19)	−0.1248 (2)	0.0491 (6)
H5C	0.0318	0.9278	−0.1810	0.059*
C6	0.4102 (3)	0.81438 (16)	0.2152 (2)	0.0367 (5)
C7	0.6114 (3)	0.86845 (18)	0.4025 (2)	0.0402 (5)
H5A	0.575 (5)	1.011 (3)	0.211 (4)	0.092 (12)*
H5B	0.443 (4)	1.032 (2)	0.290 (3)	0.065 (9)*

	U11	U22	U33	U12	U13	U23
Cl1	0.0495 (3)	0.0475 (3)	0.0356 (3)	0.0015 (2)	0.0015 (2)	0.0021 (2)
S1	0.0499 (4)	0.0593 (4)	0.0497 (4)	−0.0019 (3)	−0.0071 (3)	−0.0162 (3)
N1	0.0392 (10)	0.0627 (13)	0.0340 (10)	−0.0050 (9)	0.0007 (7)	−0.0061 (9)
N2	0.0357 (9)	0.0395 (9)	0.0353 (9)	−0.0011 (7)	0.0044 (7)	−0.0037 (7)
N3	0.0436 (10)	0.0493 (11)	0.0356 (9)	−0.0030 (9)	−0.0030 (8)	0.0022 (8)
N4	0.0440 (10)	0.0465 (11)	0.0354 (9)	−0.0058 (8)	−0.0004 (8)	−0.0004 (8)
N5	0.0633 (15)	0.0395 (12)	0.0503 (13)	0.0003 (10)	−0.0024 (11)	−0.0020 (10)
C1	0.0500 (13)	0.0506 (14)	0.0445 (12)	−0.0123 (11)	0.0063 (10)	−0.0096 (11)
C2	0.0486 (12)	0.0445 (13)	0.0402 (12)	−0.0047 (10)	0.0035 (9)	0.0002 (10)
C3	0.0324 (10)	0.0451 (12)	0.0317 (10)	−0.0027 (9)	0.0090 (8)	−0.0032 (9)
C4	0.0464 (12)	0.0421 (12)	0.0397 (11)	−0.0016 (10)	0.0034 (9)	−0.0017 (9)
C5	0.0498 (13)	0.0509 (14)	0.0403 (12)	0.0037 (11)	0.0000 (10)	0.0018 (10)
C6	0.0340 (10)	0.0409 (11)	0.0350 (10)	−0.0026 (8)	0.0081 (8)	−0.0009 (8)
C7	0.0348 (10)	0.0491 (13)	0.0347 (11)	−0.0002 (9)	0.0055 (8)	−0.0043 (9)

S1—C7	1.679 (2)	N5—H5A	0.90 (4)
N1—C5	1.328 (3)	N5—H5B	0.84 (3)
N1—C1	1.331 (3)	C1—C2	1.366 (3)
N1—H1A	0.8600	C1—H1B	0.9300
N2—C6	1.366 (3)	C2—C3	1.394 (3)
N2—C7	1.371 (3)	C2—H2A	0.9300
N2—N5	1.405 (3)	C3—C4	1.385 (3)
N3—C7	1.331 (3)	C3—C6	1.474 (3)
N3—N4	1.362 (3)	C4—C5	1.376 (3)
N3—H3A	0.8600	C4—H4B	0.9300
N4—C6	1.308 (3)	C5—H5C	0.9300
C5—N1—C1	122.28 (19)	C1—C2—H2A	120.2
C5—N1—H1A	118.9	C3—C2—H2A	120.2
C1—N1—H1A	118.9	C4—C3—C2	118.6 (2)
C6—N2—C7	108.35 (18)	C4—C3—C6	124.5 (2)
C6—N2—N5	125.26 (18)	C2—C3—C6	116.9 (2)
C7—N2—N5	125.94 (19)	C5—C4—C3	119.3 (2)
C7—N3—N4	113.60 (18)	C5—C4—H4B	120.3
C7—N3—H3A	123.2	C3—C4—H4B	120.3
N4—N3—H3A	123.2	N1—C5—C4	120.1 (2)
C6—N4—N3	104.37 (18)	N1—C5—H5C	119.9
N2—N5—H5A	105 (2)	C4—C5—H5C	119.9
N2—N5—H5B	107 (2)	N4—C6—N2	110.29 (18)
H5A—N5—H5B	114 (3)	N4—C6—C3	121.29 (19)
N1—C1—C2	120.1 (2)	N2—C6—C3	128.43 (19)
N1—C1—H1B	120.0	N3—C7—N2	103.35 (18)
C2—C1—H1B	120.0	N3—C7—S1	128.55 (17)
C1—C2—C3	119.6 (2)	N2—C7—S1	128.10 (18)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···Cl1i	0.86	2.43	3.099 (2)	135
N3—H3A···Cl1ii	0.86	2.17	3.027 (2)	176
N5—H5B···S1iii	0.84 (3)	2.72 (3)	3.466 (3)	148 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯Cl1i	0.86	2.43	3.099 (2)	135
N3—H3A⋯Cl1ii	0.86	2.17	3.027 (2)	176
N5—H5B⋯S1iii	0.84 (3)	2.72 (3)	3.466 (3)	148 (3)

Symmetry codes: (i) ; (ii) ; (iii) .