4,5-Di-amino-3-[(E,E)-4-(4,5-di-amino-4H-1,2,4-triazol-3-yl)buta-1,3-dien-yl]-4H-1,2,4-triazol-1-ium chloride.

The title compound, C8H13N10 (+)·Cl(-), is the monochlorhydrate salt of an aromatic bis-(di-amino-triazole). The cation is centrosymmetric, lying about an inversion centre (Ci symmetry) because the acidic H atom is disordered over two centrosymmetrically related ring N atoms, with equal multiplicity. It is noteworthy that protonation occurs at an N atom of the ring, instead of at the C-NH2 or N-NH2 amino groups. The chloride anions are also in special positions, as they lie on binary axes, and so the crystallographically independent unit contains half of a formula unit. The N atom of the C-NH2 group is sp (2)-hybridized and the amino group is coplanar with the triazole ring [dihedral angle = 5 (3)°], while the N atom of the N-NH2 amino group is pyramidal. The C=C bonds are in E conformations and the cation is flat because the conformation of the carbon chain is fully extended. The chloride anions are hexa-coordinated, in a distorted trigonal-prismatic geometry, and they are involved, as acceptors, in six hydrogen bonds. Chains of hydrogen-bonded cations, running along c and a + c, are generated by c-glide and C 2 rotation, respectively. This combination of N-H⋯Cl and N-H⋯N hydrogen bonds leads to the formation of a three-dimensional network.

Related literature

For semiconductor, optoelectronic and piezoelectric materials containing heterocycles, see: Wen & Liu (2010 ▶); Centore, Ricciotti et al. (2012 ▶); Centore, Concilio et al. (2012 ▶). For the structural analysis of conjugation in organic mol­ecules containing N-rich heterocycles, see: Carella, Centore, Fort et al. (2004 ▶); Centore, Fusco, Capobianco et al. (2013 ▶). For the synthesis of related compounds, see: Centore et al. (2011 ▶). For the local packing modes of heterocycles containing nitro­gen, see: Centore et al. (2013a ▶,b ▶). For H bonding in crystal structures, see: Centore, Fusco, Jazbinsek et al. (2013 ▶). For the crystal structure of the <span class="Chemical">dichlorhydrate saltn>, see: Centore, Fusco, Carella & Causà (2013 ▶).

Experimental

Crystal data

<span class="Chemical">C8H13N10 +·Cl−

M = 284.73

Monoclinic,

a = 10.360 (3) Å

b = 10.823 (4) Å

c = 11.123 (4) Å

β = 98.27 (2)°

V = 1234.2 (7) Å3

Z = 4

Mo Kα radiation

μ = 0.32 mm−1

T = 293 K

0.40 × 0.10 × 0.08 mm

Data collection

Bruker–Nonius KappaCCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T min = 0.884, T max = 0.977

4820 measured reflections

1405 independent reflections

999 reflections with I > 2σ(I)

R int = 0.048

Refinement

R[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.128

S = 1.05

1405 reflections

102 parameters

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

Δρmax = 0.28 e Å−3

Δρmin = −0.37 e Å−3

Data collection: COLLECT (Nonius, 1999 ▶); cell refinement: DIRAX/LSQ (Duisenberg et al., 2000 ▶); data reduction: EVALCCD (Duisenberg et al., 2003 ▶); program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶) and Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: WinGX (Farrugia, 2012 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813016589/bx2445sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813016589/bx2445Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813016589/bx2445Isup3.cml

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

C8H13N10+·Cl−	F(000) = 592
Mr = 284.73	Dx = 1.532 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 150 reflections
a = 10.360 (3) Å	θ = 3.7–19.8°
b = 10.823 (4) Å	µ = 0.32 mm−1
c = 11.123 (4) Å	T = 293 K
β = 98.27 (2)°	Prism, pale brown
V = 1234.2 (7) Å3	0.40 × 0.10 × 0.08 mm
Z = 4

Bruker–Nonius KappaCCD diffractometer	1405 independent reflections
Radiation source: normal-focus sealed tube	999 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.048
Detector resolution: 9 pixels mm-1	θmax = 27.5°, θmin = 3.1°
CCD rotation images, thick slices scans	h = −12→13
Absorption correction: multi-scan (SADABS; Bruker, 2001)	k = −14→12
Tmin = 0.884, Tmax = 0.977	l = −14→14
4820 measured reflections

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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.128	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ2(Fo2) + (0.057P)2 + 1.1655P] where P = (Fo2 + 2Fc2)/3
1405 reflections	(Δ/σ)max < 0.001
102 parameters	Δρmax = 0.28 e Å−3
0 restraints	Δρmin = −0.37 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	Occ. (<1)
C1	0.41283 (19)	0.7142 (2)	0.5276 (2)	0.0278 (5)
C2	0.3433 (2)	0.5222 (2)	0.51757 (19)	0.0276 (5)
C3	0.2841 (2)	0.4103 (2)	0.4657 (2)	0.0323 (5)
H3	0.2454	0.4122	0.3850	0.039*
C4	0.2814 (2)	0.3050 (2)	0.5256 (2)	0.0307 (5)
H4	0.3225	0.3021	0.6056	0.037*
N1	0.38783 (18)	0.54308 (17)	0.63082 (16)	0.0313 (5)
N2	0.43126 (19)	0.66519 (17)	0.63755 (18)	0.0317 (5)
H2	0.473 (5)	0.691 (5)	0.699 (4)	0.038*	0.50
N3	0.35804 (16)	0.62667 (16)	0.45004 (16)	0.0267 (4)
N4	0.3270 (2)	0.6457 (2)	0.32470 (18)	0.0372 (5)
H4A	0.248 (3)	0.630 (3)	0.304 (3)	0.045*
H4B	0.370 (3)	0.585 (3)	0.292 (3)	0.045*
N5	0.4393 (2)	0.82900 (19)	0.4965 (2)	0.0365 (5)
H5A	0.428 (3)	0.849 (3)	0.420 (3)	0.044*
H5B	0.477 (3)	0.884 (3)	0.558 (3)	0.044*
Cl1	0.5000	0.98424 (10)	0.7500	0.0552 (3)

	U11	U22	U33	U12	U13	U23
C1	0.0261 (10)	0.0267 (12)	0.0304 (11)	0.0013 (8)	0.0038 (8)	−0.0021 (9)
C2	0.0283 (10)	0.0270 (12)	0.0273 (11)	0.0004 (8)	0.0031 (8)	0.0020 (9)
C3	0.0352 (11)	0.0319 (13)	0.0282 (11)	−0.0011 (9)	−0.0003 (9)	−0.0045 (10)
C4	0.0351 (11)	0.0286 (12)	0.0279 (11)	−0.0017 (9)	0.0027 (8)	−0.0044 (9)
N1	0.0376 (10)	0.0278 (10)	0.0274 (10)	−0.0046 (8)	0.0008 (8)	0.0008 (8)
N2	0.0393 (10)	0.0249 (10)	0.0291 (10)	−0.0053 (8)	−0.0009 (8)	−0.0011 (8)
N3	0.0312 (9)	0.0259 (10)	0.0225 (9)	0.0021 (7)	0.0019 (7)	0.0002 (7)
N4	0.0486 (12)	0.0399 (12)	0.0226 (10)	0.0037 (10)	0.0031 (8)	0.0003 (9)
N5	0.0492 (12)	0.0249 (11)	0.0350 (11)	−0.0049 (8)	0.0046 (9)	0.0020 (9)
Cl1	0.0648 (6)	0.0474 (6)	0.0497 (6)	0.000	−0.0042 (5)	0.000

C1—N2	1.321 (3)	C4—H4	0.9300
C1—N5	1.329 (3)	N1—N2	1.395 (3)
C1—N3	1.350 (3)	N2—H2	0.80 (5)
C2—N1	1.298 (3)	N3—N4	1.400 (3)
C2—N3	1.378 (3)	N4—H4A	0.84 (3)
C2—C3	1.440 (3)	N4—H4B	0.90 (3)
C3—C4	1.322 (3)	N5—H5A	0.87 (3)
C3—H3	0.9300	N5—H5B	0.95 (3)
C4—C4i	1.434 (4)
N2—C1—N5	127.5 (2)	C1—N2—N1	109.15 (18)
N2—C1—N3	107.5 (2)	C1—N2—H2	129 (4)
N5—C1—N3	124.9 (2)	N1—N2—H2	121 (4)
N1—C2—N3	109.54 (19)	C1—N3—C2	107.25 (18)
N1—C2—C3	127.4 (2)	C1—N3—N4	123.27 (19)
N3—C2—C3	123.1 (2)	C2—N3—N4	129.47 (19)
C4—C3—C2	124.2 (2)	N3—N4—H4A	109 (2)
C4—C3—H3	117.9	N3—N4—H4B	104.1 (18)
C2—C3—H3	117.9	H4A—N4—H4B	105 (3)
C3—C4—C4i	123.8 (3)	C1—N5—H5A	118.8 (19)
C3—C4—H4	118.1	C1—N5—H5B	118.1 (17)
C4i—C4—H4	118.1	H5A—N5—H5B	123 (3)
C2—N1—N2	106.51 (18)
N1—C2—C3—C4	−9.0 (4)	N2—C1—N3—C2	0.3 (2)
N3—C2—C3—C4	172.4 (2)	N5—C1—N3—C2	−178.3 (2)
C2—C3—C4—C4i	177.9 (3)	N2—C1—N3—N4	−178.77 (19)
N3—C2—N1—N2	0.8 (2)	N5—C1—N3—N4	2.7 (3)
C3—C2—N1—N2	−177.9 (2)	N1—C2—N3—C1	−0.7 (2)
N5—C1—N2—N1	178.7 (2)	C3—C2—N3—C1	178.1 (2)
N3—C1—N2—N1	0.2 (2)	N1—C2—N3—N4	178.3 (2)
C2—N1—N2—C1	−0.6 (2)	C3—C2—N3—N4	−3.0 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···N2ii	0.80 (5)	1.97 (5)	2.695 (4)	151 (5)
N4—H4B···N1iii	0.90 (3)	2.29 (3)	3.100 (3)	149 (2)
N4—H4A···Cl1iv	0.84 (3)	2.83 (3)	3.652 (3)	165 (3)
N5—H5A···Cl1v	0.87 (3)	2.79 (3)	3.534 (2)	144 (2)
N5—H5B···Cl1	0.95 (3)	2.37 (3)	3.265 (2)	156 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯N2i	0.80 (5)	1.97 (5)	2.695 (4)	151 (5)
N4—H4B⋯N1ii	0.90 (3)	2.29 (3)	3.100 (3)	149 (2)
N4—H4A⋯Cl1iii	0.84 (3)	2.83 (3)	3.652 (3)	165 (3)
N5—H5A⋯Cl1iv	0.87 (3)	2.79 (3)	3.534 (2)	144 (2)
N5—H5B⋯Cl1	0.95 (3)	2.37 (3)	3.265 (2)	156 (2)

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