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Volume 69 
Part 10 
Pages o1522-o1523  
October 2013  

Received 6 August 2013
Accepted 29 August 2013
Online 7 September 2013

Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.003 Å
R = 0.041
wR = 0.117
Data-to-parameter ratio = 12.6
Details
Open access

2-{(E)-[(2Z)-2-(1,2-Dihydrophthalazin-1-ylidene)hydrazinylidene]methyl}phenol

aDepartment of Chemistry and Research Centre, PRNSS College, Mattanur 670 702, Kannur, Kerala, India,bDepartment of Chemistry, Faculty of Science, Eastern University, Sri Lanka, Chenkalady, Sri Lanka, and cDepartment of Applied Chemistry, Cochin University of Science and Technology, Kochi 682 022, India
Correspondence e-mail: eesans@yahoo.com

The title compound, C15H12N4O, adopts an E conformation with respect to the azomethine bond and crystallizes in its hydrazinylidene tautomeric form. The dihedral angle between the ring systems is 15.98 (7)°. The phenol O-H group forms an intramolecular O-H...N hydrogen bond. In the crystal, pairs of N-H...N and C-H...O hydrogen bonds link neighbouring molecules into centrosymmetric dimers. These dimers are interconnected by means of three types of [pi]-[pi] stacking interactions. One, with a centroid-centroid distance of 3.577 (1) Å [interplanar separation = 3.4673 (6) Å], connects adjacent molecules into centrosymmetric dimers. The other two interactions, on the outward facing sides of the dimers, are between phenol rings of neighboring molecules [centroid-centroid separation = 3.7907 (13) Å and interplanar separation = 3.5071 (8) Å], and between phthalazin units [centroid-centroid separation = 3.6001 (12) Å and interplanar separation = 3.4891 (7) Å]. In combination, the [pi]-[pi] interactions lead to the formation of infinite layers with molecules stacked along [0-11]. These layers are, in turn, connected with neighbouring layers through the N-H...N and C-H...O hydrogen bonds, yielding a three-dimensional supramolecular architecture.

Related literature

For biological properties of phthalazine and its derivatives, see: Awadallah et al. (2012[Awadallah, F. M., El-Eraky, W. I. & Saleh, D. O. (2012). Eur. J. Med. Chem. 52, 14-21.]); Minami et al. (1985[Minami, M., Togashi, H., Sano, M., Saito, I., Morii, K., Nomura, A., Yoshioka, M. & Saito, H. (1985). Hokkaido Igaku Zasshi, 60, 856-864.]); Zhang et al. (2010[Zhang, S., Zhao, Y., Liu, Y., Chen, D., Lan, W., Zhao, Q., Dong, C., Xia, L. & Gong, P. (2010). Eur. J. Med. Chem. 45, 3504-3510.]); Bian et al. (2013[Bian, M., Deng, X.-Q., Gong, G.-H., Wei, C.-X. & Quan, Z.-S. (2013). J. Enzyme Inhib. Med. Chem. 28, 792-800.]). For applications of 1-phthalazinyl hydrazones in optoelectronics, see: Caruso et al. (2005[Caruso, U., Centore, R., Panunzi, B., Roviello, A. & Tuzi, A. (2005). Eur. J. Inorg. Chem. 25, 2747-2753.]). For the synthesis of related compounds, see: El-Sherif et al. (2012[El-Sherif, A. A., Shoukry, M. M. & Abd-Elgawad, M. M. A. (2012). Spectrochim. Acta Part A, 98, 307-321.]). For related structures and background references, see: Shafiq et al. (2013[Shafiq, M., Tahir, M. N., Harrison, W. T. A., Bukhari, I. H. & Khan, I. U. (2013). Acta Cryst. E69, o164.]).

[Scheme 1]

Experimental

Crystal data
  • C15H12N4O

  • Mr = 264.29

  • Triclinic, [P \overline 1]

  • a = 6.8028 (12) Å

  • b = 8.4263 (13) Å

  • c = 11.868 (2) Å

  • [alpha] = 89.774 (9)°

  • [beta] = 83.113 (9)°

  • [gamma] = 70.356 (8)°

  • V = 635.62 (19) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.09 mm-1

  • T = 296 K

  • 0.25 × 0.20 × 0.20 mm

Data collection
  • Bruker Kappa APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2004[Bruker (2004). SADABS, APEX2, XPREP and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.978, Tmax = 0.982

  • 3781 measured reflections

  • 2204 independent reflections

  • 1623 reflections with I > 2[sigma](I)

  • Rint = 0.020

Refinement
  • R[F2 > 2[sigma](F2)] = 0.041

  • wR(F2) = 0.117

  • S = 1.03

  • 2204 reflections

  • 175 parameters

  • 2 restraints

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

  • [Delta][rho]max = 0.16 e Å-3

  • [Delta][rho]min = -0.17 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N3-H3'...N4i 0.89 (1) 2.31 (1) 3.0181 (14) 137 (2)
O1-H1A...N1 0.85 1.89 2.6362 (15) 147
C15-H15...O1i 0.93 2.59 3.224 (3) 125
Symmetry code: (i) -x+2, -y+1, -z+2.

Data collection: APEX2 (Bruker, 2004[Bruker (2004). SADABS, APEX2, XPREP and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: APEX2 and SAINT (Bruker, 2004[Bruker (2004). SADABS, APEX2, XPREP and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT and XPREP (Bruker, 2004[Bruker (2004). SADABS, APEX2, XPREP and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); 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 DIAMOND (Brandenburg, 2010[Brandenburg, K. (2010). DIAMOND. Crystal Impact GbR, Bonn, Germany.]); software used to prepare material for publication: SHELXL97 and publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: ZL2563 ).


Acknowledgements

MKP is thankful to the University Grants Commission, Bangalore, India, for the award of a Teacher Fellowship. MRPK is thankful to the UGC, New Delhi, for a UGC-BSR one-time grant to Faculty. The authors are grateful to the Sophisticated Analytical Instruments Facility, Cochin University of Science and Technology, Kochi-22, India, for the diffraction measurements.

References

Awadallah, F. M., El-Eraky, W. I. & Saleh, D. O. (2012). Eur. J. Med. Chem. 52, 14-21.  [Web of Science] [CrossRef] [ChemPort] [PubMed]
Bian, M., Deng, X.-Q., Gong, G.-H., Wei, C.-X. & Quan, Z.-S. (2013). J. Enzyme Inhib. Med. Chem. 28, 792-800.  [Web of Science] [CrossRef] [ChemPort] [PubMed]
Brandenburg, K. (2010). DIAMOND. Crystal Impact GbR, Bonn, Germany.
Bruker (2004). SADABS, APEX2, XPREP and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Caruso, U., Centore, R., Panunzi, B., Roviello, A. & Tuzi, A. (2005). Eur. J. Inorg. Chem. 25, 2747-2753.  [Web of Science] [CSD] [CrossRef]
El-Sherif, A. A., Shoukry, M. M. & Abd-Elgawad, M. M. A. (2012). Spectrochim. Acta Part A, 98, 307-321.  [ChemPort]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Minami, M., Togashi, H., Sano, M., Saito, I., Morii, K., Nomura, A., Yoshioka, M. & Saito, H. (1985). Hokkaido Igaku Zasshi, 60, 856-864.  [ChemPort] [PubMed]
Shafiq, M., Tahir, M. N., Harrison, W. T. A., Bukhari, I. H. & Khan, I. U. (2013). Acta Cryst. E69, o164.  [CSD] [CrossRef] [IUCr Journals]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Zhang, S., Zhao, Y., Liu, Y., Chen, D., Lan, W., Zhao, Q., Dong, C., Xia, L. & Gong, P. (2010). Eur. J. Med. Chem. 45, 3504-3510.  [Web of Science] [CrossRef] [ChemPort] [PubMed]


Acta Cryst (2013). E69, o1522-o1523   [ doi:10.1107/S1600536813024203 ]

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