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Volume 68 
Part 11 
Pages o3079-o3080  
November 2012  

Received 13 September 2012
Accepted 2 October 2012
Online 6 October 2012

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.004 Å
R = 0.052
wR = 0.139
Data-to-parameter ratio = 12.6
Details
Open access

2-Cyano-5-({4-[N-methyl-N-(2-hydroxyethyl)amino] phenyl}diazenyl)pyridine

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

In the title compound, C15H15N5O, the benzene and pyridine rings make a dihedral angle of 30.86 (7)°. In the crystal, chains of molecules are wrapped around the screw axes into compressed helices, through hydrogen bonding between the hydroxy and cyano groups. The chains are linked by weak C-H...N and C-H...O interactions. The [pi] conjugated unit of the molecule is almost perpendicular to the helix axis, and the formation of the helix is allowed by a gauche-type torsion angle in the hydroxyethyl tail. In this way, consecutive chromophore units along the chain are placed in a strict antiparallel arrangement, and this is energetically favoured because of the high dipole moment of the molecule.

Related literature

For general information on non-linear optical compounds, see: Singer et al. (1989[Singer, K. D., Sohn, J. E., King, L. A., Gordon, H. M., Katz, H. E. & Dirk, C. W. (1989). J. Opt. Soc. Am. B, 6, 1339-1350.]); Dalton (2002[Dalton, L. (2002). Adv. Polym. Sci. 158, 1-86.]). For structural and theoretical analysis of conjugation in push-pull molecules, see: Gainsford et al. (2008[Gainsford, G. J., Bhuiyan, M. D. H. & Kay, A. J. (2008). Acta Cryst. C64, o616-o619.]); Centore et al. (2009[Centore, R., Fusco, S., Peluso, A., Capobianco, A., Stolte, M., Archetti, G. & Kuball, H.-G. (2009). Eur. J. Org. Chem. pp. 3535-3543.]); 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.]). For the local packing modes of non-linear optical chromophores, see: Coe et al. (2000[Coe, B. J., Harris, J. A., Gelbrich, T. & Hursthouse, M. B. (2000). Acta Cryst. C56, 1487-1489.]); 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 et al. (2006[Centore, R., Carella, A., Pugliese, A., Sirigu, A. & Tuzi, A. (2006). Acta Cryst. C62, o531-o533.]). For theoretical computations on similar compounds, see: Willets et al. (1992[Willets, A., Rice, J. E. & Burland, D. M. (1992). J. Chem. Phys. 97, 7590-7599.]); Castaldo et al. (2002[Castaldo, A., Centore, R., Peluso, A., Sirigu, A. & Tuzi, A. (2002). Struct. Chem. 13, 27-36.]); Locatelli et al. (2005[Locatelli, D., Quici, S., Roberto, D. & De Angelis, F. (2005). Chem. Commun. pp. 5405-5407.]). For the CSD see: Allen (2002[Allen, F. H. (2002). Acta Cryst. B58, 380-388.]). For the synthesis of related compounds, see: Bruno et al. (2002[Bruno, V., Castaldo, A., Centore, R., Sirigu, A., Sarcinelli, F., Casalboni, M. & Pizzoferrato, R. (2002). J. Polym. Sci. Part A Polym. Chem. 40, 1468-1475.]); 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.]); Centore 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.]).

[Scheme 1]

Experimental

Crystal data
  • C15H15N5O

  • Mr = 281.32

  • Monoclinic, P 21 /c

  • a = 17.755 (8) Å

  • b = 7.240 (4) Å

  • c = 11.045 (8) Å

  • [beta] = 101.07 (5)°

  • V = 1393.4 (14) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.09 mm-1

  • T = 293 K

  • 0.40 × 0.10 × 0.05 mm

Data collection
  • Bruker-Nonius KappaCCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2001[Bruker (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.965, Tmax = 0.996

  • 8528 measured reflections

  • 2403 independent reflections

  • 1336 reflections with I > 2[sigma](I)

  • Rint = 0.069

Refinement
  • R[F2 > 2[sigma](F2)] = 0.052

  • wR(F2) = 0.139

  • S = 1.02

  • 2403 reflections

  • 191 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.14 e Å-3

  • [Delta][rho]min = -0.21 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O1-H1O...N5i 1.03 1.92 2.925 (4) 165
C6-H6...N4ii 0.93 2.74 3.637 (4) 162
C2-H2B...O1iii 0.97 2.68 3.369 (4) 129
Symmetry codes: (i) [-x, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]; (ii) -x, -y+1, -z+1; (iii) -x+1, -y+1, -z.

Data collection: COLLECT (Nonius, 1999[Nonius (1999). COLLECT. Nonius BV, Delft, The Netherlands.]); cell refinement: CELLFITW (Centore, 2004[Centore, R. (2004). CELLFITW. Università degli Studi di Napoli "Federico II", Naples, Italy.]); 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: FJ2599 ).


Acknowledgements

The authors thank the Centro Interdipartimentale di Metodologie Chimico-Fisiche, Università degli Studi di Napoli "Federico II". Thanks are also due to Professor H.-G. Kuball for the spectroscopic measurements.

References

Allen, F. H. (2002). Acta Cryst. B58, 380-388.  [ISI] [CrossRef] [details]
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]
Bruker (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Bruno, V., Castaldo, A., Centore, R., Sirigu, A., Sarcinelli, F., Casalboni, M. & Pizzoferrato, R. (2002). J. Polym. Sci. Part A Polym. Chem. 40, 1468-1475.  [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]
Castaldo, A., Centore, R., Peluso, A., Sirigu, A. & Tuzi, A. (2002). Struct. Chem. 13, 27-36.  [ISI] [CSD] [CrossRef] [ChemPort]
Centore, R. (2004). CELLFITW. Università degli Studi di Napoli "Federico II", Naples, Italy.
Centore, R., Carella, A., Pugliese, A., Sirigu, A. & Tuzi, A. (2006). Acta Cryst. C62, o531-o533.  [CSD] [CrossRef] [details]
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.  [ISI] [CrossRef] [ChemPort]
Centore, R., Fusco, S., Peluso, A., Capobianco, A., Stolte, M., Archetti, G. & Kuball, H.-G. (2009). Eur. J. Org. Chem. pp. 3535-3543.  [CrossRef]
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]
Coe, B. J., Harris, J. A., Gelbrich, T. & Hursthouse, M. B. (2000). Acta Cryst. C56, 1487-1489.  [CSD] [CrossRef] [details]
Dalton, L. (2002). Adv. Polym. Sci. 158, 1-86.  [CrossRef] [ChemPort]
Duisenberg, A. J. M., Kroon-Batenburg, L. M. J. & Schreurs, A. M. M. (2003). J. Appl. Cryst. 36, 220-229.  [ISI] [CrossRef] [ChemPort] [details]
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] [details]
Locatelli, D., Quici, S., Roberto, D. & De Angelis, F. (2005). Chem. Commun. pp. 5405-5407.  [CrossRef]
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 (1999). COLLECT. Nonius BV, Delft, The Netherlands.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Singer, K. D., Sohn, J. E., King, L. A., Gordon, H. M., Katz, H. E. & Dirk, C. W. (1989). J. Opt. Soc. Am. B, 6, 1339-1350.  [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]
Willets, A., Rice, J. E. & Burland, D. M. (1992). J. Chem. Phys. 97, 7590-7599.


Acta Cryst (2012). E68, o3079-o3080   [ doi:10.1107/S1600536812041396 ]

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