4,5-Di­amino-3-[(E,E)-4-(4,5-di­amino-4H-1,2,4-triazol-3-yl)buta-1,3-dien­yl]-4H-1,2,4-triazol-1-ium chloride

Centore, R.; Piccialli, V.

doi:10.1107/S1600536813016589

organic compounds

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ISSN: 2056-9890

Volume 69| Part 7| July 2013| Pages o1131-o1132

https://doi.org/10.1107/S1600536813016589

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4,5-Diamino-3-[(E,E)-4-(4,5-diamino-4H-1,2,4-triazol-3-yl)buta-1,3-dienyl]-4H-1,2,4-triazol-1-ium chloride

Roberto Centore ^a ^* and Vincenzo Piccialli ^a

^aDipartimento di Scienze Chimiche, Università degli Studi di Napoli 'Federico II', Complesso di Monte S. Angelo, Via Cinthia, 80126 Napoli, Italy
^*Correspondence e-mail: roberto.centore@unina.it

(Received 13 June 2013; accepted 14 June 2013; online 22 June 2013)

The title compound, C₈H₁₃N₁₀⁺·Cl⁻, is the monochlorhydrate salt of an aromatic bis(diaminotriazole). The cation is centrosymmetric, lying about an inversion centre (C_i 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 sp²-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 hexacoordinated, 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 C₂ 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 dichlorhydrate salt, see: Centore, Fusco, Carella & Causà (2013 ).

Experimental

Crystal data

C₈H₁₃N₁₀⁺·Cl⁻
M_r = 284.73
Monoclinic, C 2/c
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[F² > 2σ(F²)] = 0.047
wR(F²) = 0.128
S = 1.05
1405 reflections
102 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.28 e Å⁻³
Δρ_min = −0.37 e Å⁻³

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⋯Cl1^iv	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) $[-x+1, y, -z+{\script{3\over 2}}]$ ; (ii) $[x, -y+1, z-{\script{1\over 2}}]$ ; (iii) $[-x+{\script{1\over 2}}, -y+{\script{3\over 2}}, -z+1]$ ; (iv) -x+1, -y+2, -z+1.

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).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536813016589/bx2445sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536813016589/bx2445Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536813016589/bx2445Isup3.cml

checkCIF report

Comment top

Nitrogen rich, aromatic heterocycles have interest in the field of organic electronics for several reasons. One reason is that the Bondi van der Waals radius of nitrogen is 1.55 Å, as compared with 1.70 Å of carbon, so while the limiting interlayer distance for an all-carbon-containing planar structure is that of graphite (3.4 Å), in planar structures containing sp² hybridized nitrogen atoms, interplanar distances of 3.1 Å can be reached in principle. Another feature of sp² nitrogen atoms in heteroaromatic compounds is their capability of acting as H bonding acceptors, a feature that, if properly exploited, can lead to tighter packings. Following our interest in the synthesis of aromatic heterocycles for advanced applications in electronics, optoelectronics and photonics (Carella, Centore, Fort et al., 2004; Centore, Ricciotti et al., 2012; Centore, Concilio et al., 2012), we have recently developed the synthesis on N-rich heterocycles containing the 3,4-diamino-1,2,4-triazole unit (Centore et al., 2011; Centore, Fusco, Capobianco et al., 2013). In the present paper we report the structural investigation of the title compound, shown in the Scheme, which is the monochlorhydrate salt of a bis(3,4-diamino-1,2,4- triazole).

The molecular structure is shown in Fig. 1. The cation is formed by protonation at N2 atom of the ring, instead of C–NH₂ or N—NH₂ amino groups. The acidic H atom is found bonded both to N2 and to N2ⁱ (i= -x + 1/2, -y + 1/2, -z + 1) with equal multiplicity which is 0.5 since the cation lies in special position on crystallographic inversion centres and has (statistically) C_i symmetry. The chloride anion also lies in special position on C₂ axes and has fixed occupancy factor 0.5 too. The geometry around N5 atom is substantially planar indicating sp² hybridization (the sum of valence angles at N5 is 360 (3)°) and the plane of the amino group is coplanar with the triazole ring. This suggests partial delocalization of the lone pair of N5 towards the triazole ring, as confirmed by the short length of the bond C1–N5 (1.329 (3) Å). The geometry around N4, on the other hand, is pyramidal (the sum of valence angles at N4 is 318 (4)°). With exception for the two H atoms bonded to N4, the molecule is substantially flat, as the result of the torsion angles of the hydrocarbon chain joining the two rings. The double bonds in the hydrocarbon chain are in E configuration.

The molecules of the title compound have several H bonding donor and acceptor groups, and the crystal packing is dominated by the formation of H bonds, Table 1. Several H bonding motifs are recognized in the crystal packing and some of them are shown in Figs. 2. The chloride anion is hexacoordinated, according to a distorted trigonal prismatic geometry; it is involved, as acceptor, in six H bonds: four are formed with C–NH₂ donors and two with N–NH₂ donors. Ring patterns R²₃(10) and R²₄(8) are observed.

Cations are involved in the formation of different H bonded chains. Chains running along c are generated by the c-glide reflection through H bonding between a N–NH₂ donor and N1 acceptor of another glide-related molecule. The graph-set symbol of the H bonding pattern is C(5). Chains running along a + c are formed by H bonding between N2–H donor and N2 acceptor of a C₂ related molecule. The graph-set symbol of the H bonding pattern is C(11). It is a remarkable finding that the crystal structure of the dichlorhydrate salt is completely different, showing the formation of π-stacked infinite planar layers (Centore, Fusco, Carella & Causà, 2013).

Related literature top

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 dichlorhydrate salt, see: Centore, Fusco, Carella & Causà (2013).

Experimental top

The title compound was prepared by suspending E,E-1,4-bis(3,4-diamino-1,2,4-triazol-5-yl)-1,3-butadiene (Centore et al., 2011) in diluted hydrochloric acid (0.1 M). By heating the suspension at ebullition, a clear solution was obtained. By adding ethanol, single crystals of the chlorhydrate were obtained by slow cooling to room temperature.

Structure description top

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 dichlorhydrate salt, see: Centore, Fusco, Carella & Causà (2013).

Computing details top

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).

Figures top

	Fig. 1. ORTEP view of the molecular structure of the title compound. Thermal ellipsoids are drawn at 30% probability level. The acidic H atom is disordered over N2 and N2ⁱ (i= -x + 1/2, -y + 1/2, -z + 1) with occupancy factor 0.5. The chloride anion also has occupancy factor 1/2, as it lies on C₂ axes.
	Fig. 2. Partial crystal packing of the title compound, showing some H bonding patterns. H bonds are represented by dashed lines. Only one position of the disordered N⁺–H hydrogen atom is shown.

4,5-Diamino-3-[(E,E)-4-(4,5-diamino-4H-1,2,4-triazol-3-yl)buta-1,3-dienyl]-4H-1,2,4-triazol-1-ium chloride top

Crystal data top

C₈H₁₃N₁₀⁺·Cl⁻	F(000) = 592
M_r = 284.73	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.057P)² + 1.1655P] where P = (F_o² + 2F_c²)/3
1405 reflections	(Δ/σ)_max < 0.001
102 parameters	Δρ_max = 0.28 e Å⁻³
0 restraints	Δρ_min = −0.37 e Å⁻³

Crystal data top

C₈H₁₃N₁₀⁺·Cl⁻	V = 1234.2 (7) Å³
M_r = 284.73	Z = 4
Monoclinic, C2/c	Mo Kα radiation
a = 10.360 (3) Å	µ = 0.32 mm⁻¹
b = 10.823 (4) Å	T = 293 K
c = 11.123 (4) Å	0.40 × 0.10 × 0.08 mm
β = 98.27 (2)°

Data collection top

Bruker–Nonius KappaCCD diffractometer	1405 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2001)	999 reflections with I > 2σ(I)
T_min = 0.884, T_max = 0.977	R_int = 0.048
4820 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.047	0 restraints
wR(F²) = 0.128	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	Δρ_max = 0.28 e Å⁻³
1405 reflections	Δρ_min = −0.37 e Å⁻³
102 parameters

Special details top

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 (Å²) top

	x	y	z	U_iso*/U_eq	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)

Atomic displacement parameters (Å²) top

	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

Geometric parameters (Å, º) top

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)

Symmetry code: (i) −x+1/2, −y+1/2, −z+1.

Hydrogen-bond geometry (Å, º) top

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···Cl1^iv	0.84 (3)	2.83 (3)	3.652 (3)	165 (3)
N5—H5A···Cl1^v	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: (ii) −x+1, y, −z+3/2; (iii) x, −y+1, z−1/2; (iv) −x+1/2, −y+3/2, −z+1; (v) −x+1, −y+2, −z+1.

Experimental details

Crystal data
Chemical formula	C₈H₁₃N₁₀⁺·Cl⁻
M_r	284.73
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	293
a, b, c (Å)	10.360 (3), 10.823 (4), 11.123 (4)
β (°)	98.27 (2)
V (Å³)	1234.2 (7)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.32
Crystal size (mm)	0.40 × 0.10 × 0.08

Data collection
Diffractometer	Bruker–Nonius KappaCCD
Absorption correction	Multi-scan (SADABS; Bruker, 2001)
T_min, T_max	0.884, 0.977
No. of measured, independent and observed [I > 2σ(I)] reflections	4820, 1405, 999
R_int	0.048
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.047, 0.128, 1.05
No. of reflections	1405
No. of parameters	102
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.28, −0.37

Computer programs: COLLECT (Nonius, 1999), DIRAX/LSQ (Duisenberg et al., 2000), EVALCCD (Duisenberg et al., 2003), SIR97 (Altomare et al., 1999), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 2012) and Mercury (Macrae et al., 2006), WinGX (Farrugia, 2012).

Hydrogen-bond geometry (Å, º) top

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···Cl1^iv	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) −x+1, y, −z+3/2; (ii) x, −y+1, z−1/2; (iii) −x+1/2, −y+3/2, −z+1; (iv) −x+1, −y+2, −z+1.

Acknowledgements

The authors thank the Centro Interdipartimentale di Metodologie Chimico–Fisiche, Università degli Studi di Napoli "Federico II".

References

Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst. 32, 115–119. Web of Science CrossRef CAS IUCr Journals Google Scholar
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Volume 69| Part 7| July 2013| Pages o1131-o1132

https://doi.org/10.1107/S1600536813016589

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

4,5-Di­amino-3-[(E,E)-4-(4,5-di­amino-4H-1,2,4-triazol-3-yl)buta-1,3-dien­yl]-4H-1,2,4-triazol-1-ium chloride

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

4,5-Diamino-3-[(E,E)-4-(4,5-diamino-4H-1,2,4-triazol-3-yl)buta-1,3-dienyl]-4H-1,2,4-triazol-1-ium chloride