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Volume 69 
Part 10 
Page o1549  
October 2013  

Received 25 August 2013
Accepted 9 September 2013
Online 18 September 2013

Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.003 Å
R = 0.049
wR = 0.140
Data-to-parameter ratio = 17.1
Details
Open access

4-{(E)-[2-(Pyridin-3-ylcarbonyl)hydrazinylidene]methyl}phenyl acetate

aDepartment of Chemistry, Christ University, Hosur Road, Bangalore 560 029, 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, C15H13N3O3, exists in the E conformation with respect to the azomethane C=N double bond. The pyridyl and phenyl rings form dihedral angles of 35.67 (8) and 36.65 (7)°, respectively with the central C(=O)N2C unit. In the crystal, N-H...O and C-H...O hydrogen bonds connect the molecules into chains along the b axis. Another C-H...O interaction connects molecules along the c-axis direction, forming layers.

Related literature

For biological applications of benzohydrazones and their derivatives, see: Sreeja et al. (2004[Sreeja, P. B., Kurup, M. R. P., Kishore, A. & Jasmin, C. (2004). Polyhedron, 23, 575-581.]); Rakha et al. (1996[Rakha, T. H., Ibrahim, K. M., Abdallah, A. M. & Hassanian, M. M. (1996). Synth. React. Inorg. Met.-Org. Chem. 26, 1113-1123.]); Takahama (1996[Takahama, U. (1996). Physiol. Plant. 98, 731-736.]). For the synthesis of related compounds, see: Emmanuel et al. (2011[Emmanuel, J., Sithambaresan, M. & Kurup, M. R. P. (2011). Acta Cryst. E67, o3267.]). For related structures, see: Reshma et al. (2012[Reshma, P. R., Sithambaresan, M. & Kurup, M. R. P. (2012). Acta Cryst. E68, o2821-o2822.]).

[Scheme 1]

Experimental

Crystal data
  • C15H13N3O3

  • Mr = 283.28

  • Monoclinic, P 21 /n

  • a = 16.347 (4) Å

  • b = 5.0859 (10) Å

  • c = 18.408 (5) Å

  • [beta] = 115.311 (9)°

  • V = 1383.6 (6) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.10 mm-1

  • T = 296 K

  • 0.50 × 0.30 × 0.25 mm

Data collection
  • Bruker Kappa APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2004[Bruker (2004). APEX2, SAINT, XPREP and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.953, Tmax = 0.976

  • 9585 measured reflections

  • 3325 independent reflections

  • 2288 reflections with I > 2[sigma](I)

  • Rint = 0.023

Refinement
  • R[F2 > 2[sigma](F2)] = 0.049

  • wR(F2) = 0.140

  • S = 1.04

  • 3325 reflections

  • 195 parameters

  • 1 restraint

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

  • [Delta][rho]max = 0.31 e Å-3

  • [Delta][rho]min = -0.25 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N2-H2'...O1i 0.87 (1) 2.08 (1) 2.9107 (18) 162 (2)
C7-H7...O1i 0.93 2.48 3.251 (2) 140
C15-H15C...O3ii 0.96 2.55 3.469 (4) 161
Symmetry codes: (i) x, y+1, z; (ii) -x+1, -y, -z+1.

Data collection: APEX2 (Bruker, 2004[Bruker (2004). APEX2, SAINT, XPREP and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: APEX2 and SAINT (Bruker, 2004[Bruker (2004). APEX2, SAINT, XPREP and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT and XPREP (Bruker, 2004[Bruker (2004). APEX2, SAINT, XPREP and SADABS. 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 (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: FJ2641 ).


Acknowledgements

The authors are grateful to the Sophisticated Analytical Instruments Facility, Cochin University of Science and Technology, Kochi-22, India, for the diffraction measurements. RV and RD thank Christ University, Bangalore, India, for financial support.

References

Brandenburg, K. (2010). DIAMOND. Crystal Impact GbR, Bonn, Germany.
Bruker (2004). APEX2, SAINT, XPREP and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Emmanuel, J., Sithambaresan, M. & Kurup, M. R. P. (2011). Acta Cryst. E67, o3267.  [CSD] [CrossRef] [IUCr Journals]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Rakha, T. H., Ibrahim, K. M., Abdallah, A. M. & Hassanian, M. M. (1996). Synth. React. Inorg. Met.-Org. Chem. 26, 1113-1123.  [CrossRef] [ChemPort] [Web of Science]
Reshma, P. R., Sithambaresan, M. & Kurup, M. R. P. (2012). Acta Cryst. E68, o2821-o2822.  [CSD] [CrossRef] [ChemPort] [IUCr Journals]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Sreeja, P. B., Kurup, M. R. P., Kishore, A. & Jasmin, C. (2004). Polyhedron, 23, 575-581.  [Web of Science] [CSD] [CrossRef] [ChemPort]
Takahama, U. (1996). Physiol. Plant. 98, 731-736.  [CrossRef] [ChemPort]
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]


Acta Cryst (2013). E69, o1549  [ doi:10.1107/S1600536813025075 ]

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