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

In the cation of the title compound, C(7)H(8)N(5) (+)·Cl(-)·H(2)O, the mean planes of the pyridine and 1,2,4-triazole rings form a dihedral angle of 2.3 (1)°. The N atom of the amino group adopts a trigonal-pyramidal configuration. The N atom of the pyridine ring is protonated, forming a chloride salt. In the crystal, inter-molecular N-H⋯O, N-H⋯N, N-H⋯Cl and O-H⋯Cl hydrogen bonds link the cations, anions and water mol-ecules into layers parallel to the (1, 0, ) plane.

Related literature

For the use of <span class="Chemical">3-pyridyl-substituted 5-amino-1,2,4-triazolesn> in the synthesis of biologically active compounds, see: Lipinski (1983 ▶); Ram (1988 ▶); Akahoshi et al. (1998 ▶); Young et al. (2001 ▶); Ouyang et al. (2005 ▶); <span class="Chemical">Dolzhenko et al. (2007 ▶). For <span class="Chemical">metal complexes of 3-pyridyl-substituted 5-amino-1,2,4-tri­azoles, see: Mishra et al. (1989 ▶); Ferrer et al. (2004 ▶); Castineiras & Garcia-Santos (2008 ▶). For a theoretical investigation of the protonation of C-amino-1,2,4-triazoles, see: Anders et al. (1997 ▶). For the crystal structures of protonated C-amino-1,2,4-triazoles, see: Lynch et al. (1999 ▶); Baouab et al. (2000 ▶); Bichay et al. (2006 ▶); Guerfel et al. (2007 ▶); Matulková et al. (2007 ▶). For the ionization constants (pK α) of 3-substituted 5-amino-1H-1,2,4-triazoles, see: Voronkov et al. (1976 ▶). For the 1H and 13C NMR spectra of 3-pyridyl-substituted 5-amino-1,2,4-triazoles, see: Dolzhenko et al. (2009a ▶). For typical NMR chemical shifts of 3-substituted 5-amino-1,2,4-triazoles and their salts, see: Chernyshev et al. (2010 ▶). For the crystal structures of 3-substituted 5-amino-1H-1,2,4-triazoles, see: Rusinov et al. (1991 ▶); Daro et al. (2000 ▶); Boechat et al. (2004 ▶); Dolzhenko et al. (2009b ▶,c ▶). For the crystal structures of 3(5)-pyridyl-substituted 1,2,4-triazoles protonated at the pyridine ring, see: Ren & Jian (2008 ▶); Xie et al. (2009 ▶); Du et al. (2009 ▶). For values of bond lengths in organic compounds, see: Allen et al. (1987 ▶). For the correlation of bond lengths with bond orders between sp 2-hybridized C and N atoms, see: Burke-Laing & Laing (1976 ▶).

Experimental

Crystal data

C7<span class="Species">H8n class="Chemical">N5 +·Cl−·<spn>an class="Chemical">H2O

M = 215.65

Monoclinic,

a = 5.3411 (5) Å

b = 24.656 (3) Å

c = 7.3488 (7) Å

β = 97.62 (2)°

V = 959.22 (18) Å3

Z = 4

Ag Kα radiation

λ = 0.56085 Å

μ = 0.20 mm−1

T = 295 K

0.20 × 0.20 × 0.20 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

Absorption correction: refined from ΔF (Walker & Stuart, 1983 ▶) T min = 0.314, T max = 0.961

2389 measured reflections

2389 independent reflections

1518 reflections with I > 2σ(I)

R int = 0.000

1 standard reflections every 60 min intensity decay: 2%

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.109

S = 0.93

2389 reflections

151 parameters

<span class="Disease">H atomsn> treated by a mixture of independent and constrained refinement

Δρmax = 0.26 e Å−3

Δρmin = −0.24 e Å−3

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994 ▶); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811002406/aa2001sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811002406/aa2001Isup2.hkl

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

C7H8N5+·Cl−·H2O	F(000) = 448
Mr = 215.65	Dx = 1.493 Mg m−3
Monoclinic, P21/c	Melting point = 579–581 K
Hall symbol: -P 2ybc	Ag Kα radiation, λ = 0.56085 Å
a = 5.3411 (5) Å	Cell parameters from 25 reflections
b = 24.656 (3) Å	θ = 12.1–14.0°
c = 7.3488 (7) Å	µ = 0.20 mm−1
β = 97.62 (2)°	T = 295 K
V = 959.22 (18) Å3	Prism, yellow
Z = 4	0.20 × 0.20 × 0.20 mm

Enraf–Nonius CAD-4 diffractometer	1518 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.000
graphite	θmax = 22.0°, θmin = 1.3°
Non–profiled ω scans	h = −7→7
Absorption correction: part of the refinement model (ΔF) (Walker & Stuart, 1983)	k = 0→32
Tmin = 0.314, Tmax = 0.961	l = 0→9
2389 measured reflections	1 standard reflections every 60 min
2389 independent reflections	intensity decay: 2%

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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.109	H atoms treated by a mixture of independent and constrained refinement
S = 0.93	w = 1/[σ2(Fo2) + (0.0642P)2] where P = (Fo2 + 2Fc2)/3
2389 reflections	(Δ/σ)max = 0.001
151 parameters	Δρmax = 0.26 e Å−3
0 restraints	Δρmin = −0.24 e Å−3

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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	0.03502 (9)	0.29662 (2)	0.52890 (9)	0.0585 (2)
N1	0.4858 (3)	−0.06015 (6)	0.7559 (2)	0.0421 (4)
H1	0.458 (3)	−0.0952 (8)	0.751 (3)	0.038 (5)*
N2	0.3363 (3)	−0.01915 (6)	0.6821 (2)	0.0438 (4)
C3	0.4713 (3)	0.02346 (7)	0.7339 (3)	0.0380 (4)
N4	0.7008 (3)	0.01345 (6)	0.8344 (2)	0.0401 (4)
C5	0.7035 (3)	−0.03999 (7)	0.8458 (3)	0.0391 (4)
C13	0.3868 (3)	0.07839 (7)	0.6860 (3)	0.0376 (4)
C14	0.1558 (3)	0.08732 (8)	0.5770 (3)	0.0477 (5)
H14	0.0536	0.0583	0.5337	0.057*
C15	0.0833 (4)	0.13903 (8)	0.5355 (3)	0.0512 (5)
H15	−0.0694	0.1455	0.4620	0.061*
N16	0.2275 (3)	0.18070 (7)	0.5984 (3)	0.0514 (5)
H16	0.197 (4)	0.2140 (9)	0.580 (3)	0.053 (6)*
C17	0.4501 (4)	0.17327 (8)	0.7024 (3)	0.0535 (6)
H17	0.5484	0.2031	0.7435	0.064*
C18	0.5325 (3)	0.12272 (8)	0.7479 (3)	0.0468 (5)
H18	0.6869	0.1177	0.8207	0.056*
N51	0.8895 (3)	−0.07055 (7)	0.9294 (3)	0.0514 (5)
H51A	0.869 (4)	−0.1036 (9)	0.934 (3)	0.048 (6)*
H51B	0.994 (4)	−0.0532 (9)	0.998 (3)	0.063 (7)*
O1	0.4229 (4)	0.67460 (7)	0.2570 (3)	0.0635 (5)
H1A	0.309 (6)	0.6799 (12)	0.333 (4)	0.092 (11)*
H1B	0.562 (6)	0.6872 (11)	0.319 (4)	0.092 (10)*

	U11	U22	U33	U12	U13	U23
Cl1	0.0424 (3)	0.0401 (3)	0.0893 (5)	0.0049 (2)	−0.0051 (3)	0.0026 (3)
N1	0.0292 (7)	0.0325 (8)	0.0603 (11)	−0.0045 (6)	−0.0100 (7)	0.0005 (8)
N2	0.0291 (7)	0.0428 (8)	0.0560 (10)	−0.0051 (6)	−0.0078 (7)	−0.0022 (8)
C3	0.0237 (8)	0.0429 (10)	0.0452 (11)	−0.0004 (7)	−0.0041 (7)	−0.0041 (8)
N4	0.0289 (7)	0.0330 (7)	0.0545 (10)	−0.0017 (6)	−0.0082 (7)	−0.0009 (7)
C5	0.0283 (8)	0.0359 (8)	0.0501 (11)	−0.0031 (7)	−0.0063 (7)	−0.0005 (8)
C13	0.0273 (8)	0.0392 (9)	0.0450 (10)	0.0019 (7)	−0.0002 (7)	−0.0004 (8)
C14	0.0320 (9)	0.0486 (11)	0.0584 (13)	−0.0007 (8)	−0.0092 (9)	−0.0014 (9)
C15	0.0312 (9)	0.0532 (12)	0.0650 (14)	0.0094 (8)	−0.0090 (9)	0.0057 (10)
N16	0.0413 (9)	0.0419 (9)	0.0686 (13)	0.0117 (7)	−0.0012 (8)	0.0048 (9)
C17	0.0393 (10)	0.0464 (11)	0.0706 (16)	0.0013 (9)	−0.0078 (10)	−0.0023 (10)
C18	0.0285 (9)	0.0426 (10)	0.0657 (13)	0.0029 (8)	−0.0076 (9)	0.0008 (10)
N51	0.0361 (8)	0.0326 (9)	0.0784 (14)	−0.0011 (7)	−0.0187 (8)	0.0002 (9)
O1	0.0426 (9)	0.0564 (10)	0.0867 (13)	0.0052 (7)	−0.0094 (10)	−0.0090 (9)

N4—C5	1.320 (2)	C15—N16	1.330 (3)
N4—C3	1.367 (2)	C15—H15	0.9300
C5—N51	1.330 (2)	N16—C17	1.338 (3)
C5—N1	1.353 (2)	N16—H16	0.85 (2)
N1—N2	1.356 (2)	C17—C18	1.349 (3)
N1—H1	0.876 (19)	C17—H17	0.9300
N2—C3	1.302 (2)	C18—H18	0.9300
C3—C13	1.456 (2)	N51—H51A	0.82 (2)
C13—C18	1.383 (2)	N51—H51B	0.82 (2)
C13—C14	1.396 (2)	O1—H1A	0.89 (3)
C14—C15	1.355 (3)	O1—H1B	0.88 (3)
C14—H14	0.9300
C5—N4—C3	102.47 (14)	N16—C15—C14	120.89 (17)
N4—C5—N51	126.56 (17)	N16—C15—H15	119.6
N4—C5—N1	109.53 (15)	C14—C15—H15	119.6
N51—C5—N1	123.90 (18)	C15—N16—C17	121.52 (18)
C5—N1—N2	110.08 (15)	C15—N16—H16	127.1 (16)
C5—N1—H1	120.6 (12)	C17—N16—H16	111.3 (16)
N2—N1—H1	129.3 (12)	N16—C17—C18	120.25 (18)
C3—N2—N1	102.18 (14)	N16—C17—H17	119.9
N2—C3—N4	115.73 (16)	C18—C17—H17	119.9
N2—C3—C13	122.53 (15)	C17—C18—C13	119.87 (17)
N4—C3—C13	121.73 (15)	C17—C18—H18	120.1
C18—C13—C14	118.66 (17)	C13—C18—H18	120.1
C18—C13—C3	120.84 (15)	C5—N51—H51A	118.8 (15)
C14—C13—C3	120.50 (16)	C5—N51—H51B	113.2 (17)
C15—C14—C13	118.80 (17)	H51A—N51—H51B	125 (2)
C15—C14—H14	120.6	H1A—O1—H1B	103 (3)
C13—C14—H14	120.6
C3—N4—C5—N51	179.2 (2)	N2—C3—C13—C14	−1.6 (3)
C3—N4—C5—N1	0.1 (2)	N4—C3—C13—C14	177.42 (19)
N4—C5—N1—N2	0.4 (2)	C18—C13—C14—C15	0.2 (3)
N51—C5—N1—N2	−178.75 (19)	C3—C13—C14—C15	179.92 (19)
C5—N1—N2—C3	−0.8 (2)	C13—C14—C15—N16	−0.6 (3)
N1—N2—C3—N4	0.9 (2)	C14—C15—N16—C17	0.9 (3)
N1—N2—C3—C13	179.91 (17)	C15—N16—C17—C18	−0.7 (3)
C5—N4—C3—N2	−0.6 (2)	N16—C17—C18—C13	0.3 (3)
C5—N4—C3—C13	−179.68 (18)	C14—C13—C18—C17	0.0 (3)
N2—C3—C13—C18	178.20 (19)	C3—C13—C18—C17	−179.8 (2)
N4—C3—C13—C18	−2.8 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1i	0.876 (19)	1.97 (2)	2.842 (2)	175.0 (18)
N16—H16···Cl1	0.85 (2)	2.22 (2)	3.0574 (18)	169 (2)
N51—H51A···Cl1ii	0.82 (2)	2.52 (2)	3.3092 (18)	160.5 (19)
N51—H51B···N4iii	0.82 (2)	2.15 (2)	2.963 (2)	174 (2)
O1—H1A···Cl1iv	0.89 (3)	2.29 (3)	3.159 (2)	167 (3)
O1—H1B···Cl1v	0.88 (3)	2.32 (3)	3.187 (2)	168 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1i	0.876 (19)	1.97 (2)	2.842 (2)	175.0 (18)
N16—H16⋯Cl1	0.85 (2)	2.22 (2)	3.0574 (18)	169 (2)
N51—H51A⋯Cl1ii	0.82 (2)	2.52 (2)	3.3092 (18)	160.5 (19)
N51—H51B⋯N4iii	0.82 (2)	2.15 (2)	2.963 (2)	174 (2)
O1—H1A⋯Cl1iv	0.89 (3)	2.29 (3)	3.159 (2)	167 (3)
O1—H1B⋯Cl1v	0.88 (3)	2.32 (3)	3.187 (2)	168 (2)

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