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Volume 69 
Part 7 
Pages o1131-o1132  
July 2013  

Received 13 June 2013
Accepted 14 June 2013
Online 22 June 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.003 Å
R = 0.047
wR = 0.128
Data-to-parameter ratio = 13.8
Details
Open access

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

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

The title compound, C8H13N10+·Cl-, is the monochlorhydrate salt of an aromatic bis(diaminotriazole). 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 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[Wen, Y. & Liu, Y. (2010). Adv. Mater. 22, 1331-1345.]); Centore, Ricciotti et al. (2012[Centore, R., Ricciotti, L., Carella, A., Roviello, A., Causà, M., Barra, M., Ciccullo, F. & Cassinese, A. (2012). Org. Electron. 13, 2083-2093.]); Centore, Concilio et al. (2012[Centore, R., Concilio, A., Borbone, F., Fusco, S., Carella, A., Roviello, A., Stracci, G. & Gianvito, A. (2012). J. Polym. Sci. Part B Polym. Phys. 50, 650-655.]). For the structural analysis of conjugation in organic molecules containing N-rich heterocycles, see: Carella, Centore, Fort et al. (2004[Carella, A., Centore, R., Fort, A., Peluso, A., Sirigu, A. & Tuzi, A. (2004). Eur. J. Org. Chem. pp. 2620-2626.]); Centore, Fusco, Capobianco et al. (2013[Centore, R., Fusco, S., Capobianco, A., Piccialli, V., Zaccaria, S. & Peluso, A. (2013). Eur. J. Org. Chem. pp. 3721-3728.]). For the synthesis of related compounds, see: Centore et al. (2011[Centore, R., Carella, A. & Fusco, S. (2011). Struct. Chem. 22, 1095-1103.]). For the local packing modes of heterocycles containing nitrogen, see: Centore et al. (2013a[Centore, R., Piccialli, V. & Tuzi, A. (2013a). Acta Cryst. E69, o667-o668.],b[Centore, R., Piccialli, V. & Tuzi, A. (2013b). Acta Cryst. E69, o802-o803.]). For H bonding in crystal structures, see: Centore, Fusco, Jazbinsek et al. (2013[Centore, R., Fusco, S., Jazbinsek, M., Capobianco, A. & Peluso, A. (2013). CrystEngComm, 15, 3318-3325.]). For the crystal structure of the dichlorhydrate salt, see: Centore, Fusco, Carella & Causà (2013[Centore, R., Fusco, S., Carella, A. & Causà, M. (2013). Cryst. Growth Des. doi:10.1021/cg400750d.]).

[Scheme 1]

Experimental

Crystal data
  • C8H13N10+·Cl-

  • Mr = 284.73

  • Monoclinic, C 2/c

  • a = 10.360 (3) Å

  • b = 10.823 (4) Å

  • c = 11.123 (4) Å

  • [beta] = 98.27 (2)°

  • V = 1234.2 (7) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 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[Bruker (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.884, Tmax = 0.977

  • 4820 measured reflections

  • 1405 independent reflections

  • 999 reflections with I > 2[sigma](I)

  • Rint = 0.048

Refinement
  • R[F2 > 2[sigma](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

  • [Delta][rho]max = 0.28 e Å-3

  • [Delta][rho]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...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) [-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[Nonius (1999). COLLECT. Nonius BV, Delft, The Netherlands.]); cell refinement: DIRAX/LSQ (Duisenberg et al., 2000[Duisenberg, A. J. M., Hooft, R. W. W., Schreurs, A. M. M. & Kroon, J. (2000). J. Appl. Cryst. 33, 893-898.]); data reduction: EVALCCD (Duisenberg et al., 2003[Duisenberg, A. J. M., Kroon-Batenburg, L. M. J. & Schreurs, A. M. M. (2003). J. Appl. Cryst. 36, 220-229.]); program(s) used to solve structure: SIR97 (Altomare et al., 1999[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.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) and Mercury (Macrae et al., 2006[Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457.]); software used to prepare material for publication: WinGX (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BX2445 ).


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] [ChemPort] [IUCr Journals]
Bruker (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Carella, A., Centore, R., Fort, A., Peluso, A., Sirigu, A. & Tuzi, A. (2004). Eur. J. Org. Chem. pp. 2620-2626.  [CSD] [CrossRef]
Centore, R., Carella, A. & Fusco, S. (2011). Struct. Chem. 22, 1095-1103.  [Web of Science] [CSD] [CrossRef]
Centore, R., Concilio, A., Borbone, F., Fusco, S., Carella, A., Roviello, A., Stracci, G. & Gianvito, A. (2012). J. Polym. Sci. Part B Polym. Phys. 50, 650-655.  [Web of Science] [CrossRef] [ChemPort]
Centore, R., Fusco, S., Capobianco, A., Piccialli, V., Zaccaria, S. & Peluso, A. (2013). Eur. J. Org. Chem. pp. 3721-3728.  [CSD] [CrossRef]
Centore, R., Fusco, S., Carella, A. & Causà, M. (2013). Cryst. Growth Des. doi:10.1021/cg400750d.
Centore, R., Fusco, S., Jazbinsek, M., Capobianco, A. & Peluso, A. (2013). CrystEngComm, 15, 3318-3325.  [Web of Science] [CSD] [CrossRef] [ChemPort]
Centore, R., Piccialli, V. & Tuzi, A. (2013a). Acta Cryst. E69, o667-o668.  [CSD] [CrossRef] [ChemPort] [IUCr Journals]
Centore, R., Piccialli, V. & Tuzi, A. (2013b). Acta Cryst. E69, o802-o803.  [CSD] [CrossRef] [ChemPort] [IUCr Journals]
Centore, R., Ricciotti, L., Carella, A., Roviello, A., Causà, M., Barra, M., Ciccullo, F. & Cassinese, A. (2012). Org. Electron. 13, 2083-2093.  [Web of Science] [CrossRef] [ChemPort]
Duisenberg, A. J. M., Hooft, R. W. W., Schreurs, A. M. M. & Kroon, J. (2000). J. Appl. Cryst. 33, 893-898.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Duisenberg, A. J. M., Kroon-Batenburg, L. M. J. & Schreurs, A. M. M. (2003). J. Appl. Cryst. 36, 220-229.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Nonius (1999). COLLECT. Nonius BV, Delft, The Netherlands.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Wen, Y. & Liu, Y. (2010). Adv. Mater. 22, 1331-1345.  [Web of Science] [CrossRef] [ChemPort] [PubMed]


Acta Cryst (2013). E69, o1131-o1132   [ doi:10.1107/S1600536813016589 ]

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