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Volume 69 
Part 5 
Pages o802-o803  
May 2013  

Received 19 April 2013
Accepted 24 April 2013
Online 27 April 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.008 Å
R = 0.075
wR = 0.216
Data-to-parameter ratio = 15.6
Details
Open access

3,3'-({4-[(4,5-Dicyano-1H-imidazol-2-yl)diazenyl]phenyl}imino)dipropionic acid

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, C17H15N7O4, is a push-pull non-linear optical chromophore containing a dialkylamino donor group and the dicyanoimidazolyl acceptor separated by a [pi]-conjugated path. The benzene and imidazole rings are not coplanar, making a dihedral angle of 10.0 (2)°. In the crystal, molecules are linked by an extended set of hydrogen bonds and several motifs are recognized. Pairs of molecules are held together by hydrogen bonding between carboxy O-H donor groups and diazenyl N-atom acceptors, forming R22(24) ring patterns across inversion centres. Four-molecule R44(28) ring motifs are formed, again across inversion centres, through hydrogen bonding involving carboxy O-H donor groups and diazenyl and imidazole N-atom acceptors. Four-molecule R44(42) patterns are formed among molecules related by translation and involve carboxy O-H and imidazole N-H donor groups with carbonyl O-atom and imidazole N-atom acceptors.

Related literature

For a general survey of advanced materials based on heterocycles, see: Dalton (2002[Dalton, L. (2002). Adv. Polym. Sci. 158, 1-86.]); Heeger (2010[Heeger, A. J. (2010). Chem. Soc. Rev. 39, 2354-2371.]). For semiconductor, optoelectronic and piezoelectric materials containing heterocycles, see: 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 structural analysis of conjugation in heterocycle-based organic molecules, 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.]); Gainsford et al. (2008[Gainsford, G. J., Bhuiyan, M. D. H. & Kay, A. J. (2008). Acta Cryst. C64, o616-o619.]). For structural and theoretical analysis of conjugation in metallorganic compounds containing heterocycles, see: Takjoo et al. (2011[Takjoo, R., Centore, R., Hakimi, M., Beyramabadi, A. S. & Morsali, A. (2011). Inorg. Chim. Acta, 371, 36-41.]); Takjoo & Centore (2013[Takjoo, R. & Centore, R. (2013). J. Mol. Struct. 1031, 180-185.]). For theoretical computations on [pi]-conjugated compounds, see: Capobianco et al. (2012[Capobianco, A., Esposito, A., Caruso, T., Borbone, F., Carella, A., Centore, R. & Peluso, A. (2012). Eur. J. Org. Chem. pp. 2980-2989.], 2013[Capobianco, A., Centore, R., Noce, C. & Peluso, A. (2013). Chem. Phys. 411, 11-16.]). For the synthesis of related heterocyclic compounds, see: Carella, Centore, Sirigu et al. (2004[Carella, A., Centore, R., Sirigu, A., Tuzi, A., Quatela, A., Schutzmann, S. & Casalboni, M. (2004). Macromol. Chem. Phys. 205, 1948-1954.]); Piccialli et al. (2013[Piccialli, V., D'Errico, S., Borbone, N., Oliviero, G., Centore, R. & Zaccaria, S. (2013). Eur. J. Org. Chem. pp. 1781-1789.]); Centore, Fusco, Capobianco et al. (2013[Centore, R., Fusco, S., Capobianco, A., Piccialli, V., Zaccaria, S. & Peluso, A. (2013). Eur. J. Org. Chem. doi:10.1002/ejoc.201201653.]). For the local packing modes of non-linear optical chromophores see: Thallapally et al. (2002[Thallapally, P. K., Desiraju, G. R., Bagieu-Beucher, M., Masse, R., Bourgogne, C. & Nicoud, J.-F. (2002). Chem. Commun. pp. 1052-1053.]); Centore & Piccialli (2012[Centore, R. & Piccialli, V. (2012). Acta Cryst. E68, o3079-o3080.]); Centore, Piccialli & Tuzi (2013[Centore, R., Piccialli, V. & Tuzi, A. (2013). Acta Cryst. E69, o667-o668.]). For hydrogen bonding in crystal structures, see: Allen et al. (1999[Allen, F. H., Motherwell, W. D. S., Raithby, P. R., Shields, G. P. & Taylor, R. (1999). New J. Chem. pp. 25-34.]); Steiner (2002[Steiner, T. (2002). Angew. Chem. Int. Ed. 41, 48-76.]); Centore, Jazbinsek et al. (2012[Centore, R., Jazbinsek, M., Tuzi, A., Roviello, A., Capobianco, A. & Peluso, A. (2012). CrystEngComm, 14, 2645-2653.]); Centore, Fusco, Jazbinsek et al. (2013[Centore, R., Fusco, S., Jazbinsek, M., Capobianco, A. & Peluso, A. (2013). CrystEngComm, 15, 3318-3325.]). For the synthesis of similar diazo-chromophores, see: Centore et al. (2007[Centore, R., Riccio, P., Fusco, S., Carella, A., Quatela, A., Schutzmann, S., Stella, F. & De Matteis, F. (2007). J. Polym. Sci. Part A Polym. Chem. 45, 2719-2725.]).

[Scheme 1]

Experimental

Crystal data
  • C17H15N7O4

  • Mr = 381.36

  • Triclinic, [P \overline 1]

  • a = 6.895 (5) Å

  • b = 10.443 (3) Å

  • c = 13.373 (3) Å

  • [alpha] = 105.40 (2)°

  • [beta] = 103.96 (4)°

  • [gamma] = 104.84 (4)°

  • V = 846.5 (7) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.11 mm-1

  • T = 293 K

  • 0.26 × 0.13 × 0.07 mm

Data collection
  • Enraf-Nonius MACH3 diffractometer

  • 4256 measured reflections

  • 4082 independent reflections

  • 1220 reflections with I > 2[sigma](I)

  • Rint = 0.074

  • 1 standard reflections every 120 min intensity decay: none

Refinement
  • R[F2 > 2[sigma](F2)] = 0.075

  • wR(F2) = 0.216

  • S = 0.91

  • 4082 reflections

  • 262 parameters

  • H atoms treated by a mixture of independent and constrained refinement

  • [Delta][rho]max = 0.30 e Å-3

  • [Delta][rho]min = -0.33 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O2-H2...N5i 0.80 (6) 2.12 (6) 2.896 (6) 162 (6)
O3-H3...N3ii 0.88 (5) 1.89 (6) 2.750 (6) 165 (5)
N4-H4...O4iii 0.81 (5) 1.98 (5) 2.740 (6) 156 (5)
Symmetry codes: (i) x+1, y, z+1; (ii) -x-1, -y, -z; (iii) x+1, y+1, z.

Data collection: MACH3/PC Software (Nonius, 1996[Nonius (1996). MACH3/PC and CAD-4-PC. Nonius BV, Delft, The Nehterlands.]); cell refinement: CELLFITW (Centore, 2004[Centore, R. (2004). CELLFITW. Università degli Studi di Napoli "Federico II", Naples, Italy.]); data reduction: XCAD4 (Harms & Wocadlo, 1995[Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany.]); 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: BX2439 ).


Acknowledgements

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

References

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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.  [ISI] [CrossRef] [ChemPort] [details]
Capobianco, A., Centore, R., Noce, C. & Peluso, A. (2013). Chem. Phys. 411, 11-16.  [ISI] [CrossRef] [ChemPort]
Capobianco, A., Esposito, A., Caruso, T., Borbone, F., Carella, A., Centore, R. & Peluso, A. (2012). Eur. J. Org. Chem. pp. 2980-2989.  [CSD] [CrossRef]
Carella, A., Centore, R., Fort, A., Peluso, A., Sirigu, A. & Tuzi, A. (2004). Eur. J. Org. Chem. pp. 2620-2626.  [CSD] [CrossRef]
Carella, A., Centore, R., Sirigu, A., Tuzi, A., Quatela, A., Schutzmann, S. & Casalboni, M. (2004). Macromol. Chem. Phys. 205, 1948-1954.  [ISI] [CSD] [CrossRef] [ChemPort]
Centore, R. (2004). CELLFITW. Università degli Studi di Napoli "Federico II", Naples, Italy.
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Centore, R., Fusco, S., Capobianco, A., Piccialli, V., Zaccaria, S. & Peluso, A. (2013). Eur. J. Org. Chem. doi:10.1002/ejoc.201201653.
Centore, R., Fusco, S., Jazbinsek, M., Capobianco, A. & Peluso, A. (2013). CrystEngComm, 15, 3318-3325.  [CSD] [CrossRef] [ChemPort]
Centore, R., Jazbinsek, M., Tuzi, A., Roviello, A., Capobianco, A. & Peluso, A. (2012). CrystEngComm, 14, 2645-2653.  [ISI] [CSD] [CrossRef] [ChemPort]
Centore, R. & Piccialli, V. (2012). Acta Cryst. E68, o3079-o3080.  [CSD] [CrossRef] [ChemPort] [details]
Centore, R., Piccialli, V. & Tuzi, A. (2013). Acta Cryst. E69, o667-o668.  [CrossRef] [details]
Centore, R., Riccio, P., Fusco, S., Carella, A., Quatela, A., Schutzmann, S., Stella, F. & De Matteis, F. (2007). J. Polym. Sci. Part A Polym. Chem. 45, 2719-2725.  [CrossRef] [ChemPort]
Centore, R., Ricciotti, L., Carella, A., Roviello, A., Causà, M., Barra, M., Ciccullo, F. & Cassinese, A. (2012). Org. Electron. 13, 2083-2093.  [ISI] [CrossRef] [ChemPort]
Dalton, L. (2002). Adv. Polym. Sci. 158, 1-86.  [CrossRef] [ChemPort]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Gainsford, G. J., Bhuiyan, M. D. H. & Kay, A. J. (2008). Acta Cryst. C64, o616-o619.  [CSD] [CrossRef] [ChemPort] [details]
Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany.
Heeger, A. J. (2010). Chem. Soc. Rev. 39, 2354-2371.  [ISI] [CrossRef] [ChemPort] [PubMed]
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.  [ISI] [CrossRef] [ChemPort] [details]
Nonius (1996). MACH3/PC and CAD-4-PC. Nonius BV, Delft, The Nehterlands.
Piccialli, V., D'Errico, S., Borbone, N., Oliviero, G., Centore, R. & Zaccaria, S. (2013). Eur. J. Org. Chem. pp. 1781-1789.  [CSD] [CrossRef]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]
Steiner, T. (2002). Angew. Chem. Int. Ed. 41, 48-76.  [ISI] [CrossRef] [ChemPort]
Takjoo, R. & Centore, R. (2013). J. Mol. Struct. 1031, 180-185.  [ISI] [CSD] [CrossRef] [ChemPort]
Takjoo, R., Centore, R., Hakimi, M., Beyramabadi, A. S. & Morsali, A. (2011). Inorg. Chim. Acta, 371, 36-41.  [ISI] [CSD] [CrossRef] [ChemPort]
Thallapally, P. K., Desiraju, G. R., Bagieu-Beucher, M., Masse, R., Bourgogne, C. & Nicoud, J.-F. (2002). Chem. Commun. pp. 1052-1053.  [CSD] [CrossRef]


Acta Cryst (2013). E69, o802-o803   [ doi:10.1107/S1600536813011185 ]

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