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Volume 69 
Part 4 
Pages o586-o587  
April 2013  

Received 5 March 2013
Accepted 19 March 2013
Online 23 March 2013

Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.002 Å
R = 0.037
wR = 0.109
Data-to-parameter ratio = 11.0
Details
Open access

(2E)-2-(3-Ethoxy-2-hydroxybenzylidene)hydrazinecarboxamide

aDepartment of Applied Chemistry, Cochin University of Science and Technology, Kochi 682 022, India, and bDepartment of Chemistry, Faculty of Science, Eastern University, Sri Lanka, Chenkalady, Sri Lanka
Correspondence e-mail: eesans@yahoo.com

The title compound, C10H13N3O3, adopts an E conformation with respect to the azomethine bond and crystallizes in the amide form. A classical intramolecular O-H...N hydrogen bond is present. The two N atoms of the hydrazinecarboxamide unit are also involved in intermolecular N-H...O hydrogen bonds, with the O atom of the hydrazinecarboxamide group acting as the acceptor. Pairs of N-H...O hydrogen bond link the molecules into centrosymmetric dimers, which are linked by further N-H...O hydrogen bonds into chains along the b axis. The chains are linked by C-H...[pi] interactions.

Related literature

For biological applications of hydrazinecarboxamide and its derivatives, see: Afrasiabi et al. (2005[Afrasiabi, Z., Sinn, E., Lin, W., Ma, Y., Campana, C. & Padhye, S. (2005). J. Inorg. Biochem. 99, 1526-1531.]); Siji et al. (2010[Siji, V. L., Sudarsanakumar, M. R., Suma, S. & Kurup, M. R. P. (2010). Spectrochim. Acta Part A, 76, 22-28.]); Beraldo & Gambino (2004[Beraldo, H. & Gambino, D. (2004). Mini Rev. Med. Chem. 4, 31-39.]). For related structures and background references, see: Sithambaresan & Kurup (2011[Sithambaresan, M. & Kurup, M. R. P. (2011). Acta Cryst. E67, o2972.]); Noblía et al. (2004,[Noblía, P., Baran, E. J., Otero, L., Draper, P., Cerecetto, H., González, M., Piro, O. E., Castellano, E. E., Inohara, T., Adachi, Y., Sakurai, H. & Gambino, D. (2004). Eur. J. Inorg. Chem. pp. 322-328.] 2005[Noblía, P., Vieites, M., Parajón-Costa, P., Baran, E. J., Cerecetto, H., Draper, P., González, M., Piro, O. E., Castellano, E. E., Azqueta, A., López, A., Monge-Vega, A. & Gambino, D. (2005). J. Inorg. Biochem. 99, 443-451.]); Benítez et al. (2009[Benítez, J., Guggeri, L., Tomaz, I., Arrambide, G., Navarro, M., Costa Pessoa, J., Garat, B. & Gambino, D. (2009). J. Inorg. Biochem. 103, 609-616.], 2011[Benítez, J., Becco, L., Correia, I., Leal, S. M., Guiset, H., Costa Pessoa, J., Lorenzo, J., Aviles, F., Escobar, P., Moreno, V., Garat, B. & Gambino, D. (2011). J. Inorg. Biochem. 105, 303-312.]); Rivadeneira et al. (2009[Rivadeneira, J., Barrio, D., Arrambide, G., Gambino, D., Bruzzone, L. & Etcheverry, S. (2009). J. Inorg. Biochem. 103, 633-642.]); Gambino et al. (2011[Gambino, D., Fernándeza, M., Santosa, D., Etcheverría, G. A., Piro, O. E., Pavan, F. R., Leite, C. Q. F., Tomaz, I. & Marques, F. (2011). Polyhedron, 30, 1360-1366.]). For standard bond-length data, see: Allen et al. (1987[Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.]); Kala et al. (2007[Kala, U. L., Suma, S., Kurup, M. R. P., Suja, K. & John, R. P. (2007). Polyhedron, 26, 1427-1435.]). For the synthesis, see: Sreekanth et al. (2004[Sreekanth, A., Kala, U. L., Nayar, C. R. & Kurup, M. R. P. (2004). Polyhedron, 23, 41-47.]).

[Scheme 1]

Experimental

Crystal data
  • C10H13N3O3

  • Mr = 223.23

  • Triclinic, [P \overline 1]

  • a = 5.0676 (4) Å

  • b = 7.0426 (7) Å

  • c = 15.8394 (15) Å

  • [alpha] = 97.509 (4)°

  • [beta] = 98.819 (3)°

  • [gamma] = 105.790 (4)°

  • V = 528.62 (8) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.11 mm-1

  • T = 296 K

  • 0.30 × 0.25 × 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 = 0.969, Tmax = 0.979

  • 2559 measured reflections

  • 1794 independent reflections

  • 1496 reflections with I > 2[sigma](I)

  • Rint = 0.011

Refinement
  • R[F2 > 2[sigma](F2)] = 0.037

  • wR(F2) = 0.109

  • S = 1.05

  • 1794 reflections

  • 163 parameters

  • 5 restraints

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

  • [Delta][rho]max = 0.15 e Å-3

  • [Delta][rho]min = -0.18 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C1-C6 ring

D-H...A D-H H...A D...A D-H...A
N3-H3A...O3i 0.85 (1) 2.06 (1) 2.9034 (19) 173 (2)
O2-H2'...N1 0.84 (1) 1.89 (1) 2.6736 (15) 155 (2)
N2-H2...O3ii 0.87 (1) 2.06 (1) 2.8965 (17) 161 (2)
C9-H9A...Cgiii 0.97 2.75 3.5896 (19) 145
Symmetry codes: (i) -x+3, -y+3, -z+1; (ii) -x+3, -y+2, -z+1; (iii) x-1, y, z.

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: FJ2621 ).


Acknowledgements

AAA thanks the Council of Scientific and Industrial Research, New Delhi, India, for financial support in the form of a Junior Research Fellowship. The authors are grateful to the Sophisticated Analytical Instruments Facility, Cochin University of Science and Technology, Kochi-22, India, for the data collection. MRPK thanks the University Grants Commission, New Delhi, for a UGC-BSR one-time grant to faculty.

References

Afrasiabi, Z., Sinn, E., Lin, W., Ma, Y., Campana, C. & Padhye, S. (2005). J. Inorg. Biochem. 99, 1526-1531.  [ISI] [CSD] [CrossRef] [PubMed] [ChemPort]
Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.
Benítez, J., Becco, L., Correia, I., Leal, S. M., Guiset, H., Costa Pessoa, J., Lorenzo, J., Aviles, F., Escobar, P., Moreno, V., Garat, B. & Gambino, D. (2011). J. Inorg. Biochem. 105, 303-312.  [ISI] [PubMed]
Benítez, J., Guggeri, L., Tomaz, I., Arrambide, G., Navarro, M., Costa Pessoa, J., Garat, B. & Gambino, D. (2009). J. Inorg. Biochem. 103, 609-616.  [ISI] [PubMed]
Beraldo, H. & Gambino, D. (2004). Mini Rev. Med. Chem. 4, 31-39.  [CrossRef] [PubMed] [ChemPort]
Brandenburg, K. (2010). DIAMOND. Crystal Impact GbR, Bonn, Germany.
Bruker (2004). SADABS, APEX2, XPREP and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Gambino, D., Fernándeza, M., Santosa, D., Etcheverría, G. A., Piro, O. E., Pavan, F. R., Leite, C. Q. F., Tomaz, I. & Marques, F. (2011). Polyhedron, 30, 1360-1366.  [ISI] [CSD] [CrossRef] [ChemPort]
Kala, U. L., Suma, S., Kurup, M. R. P., Suja, K. & John, R. P. (2007). Polyhedron, 26, 1427-1435.  [ISI] [CSD] [CrossRef] [ChemPort]
Noblía, P., Vieites, M., Parajón-Costa, P., Baran, E. J., Cerecetto, H., Draper, P., González, M., Piro, O. E., Castellano, E. E., Azqueta, A., López, A., Monge-Vega, A. & Gambino, D. (2005). J. Inorg. Biochem. 99, 443-451.  [ISI] [PubMed]
Noblía, P., Baran, E. J., Otero, L., Draper, P., Cerecetto, H., González, M., Piro, O. E., Castellano, E. E., Inohara, T., Adachi, Y., Sakurai, H. & Gambino, D. (2004). Eur. J. Inorg. Chem. pp. 322-328.
Rivadeneira, J., Barrio, D., Arrambide, G., Gambino, D., Bruzzone, L. & Etcheverry, S. (2009). J. Inorg. Biochem. 103, 633-642.  [ISI] [CrossRef] [PubMed] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Siji, V. L., Sudarsanakumar, M. R., Suma, S. & Kurup, M. R. P. (2010). Spectrochim. Acta Part A, 76, 22-28.  [ChemPort]
Sithambaresan, M. & Kurup, M. R. P. (2011). Acta Cryst. E67, o2972.  [CSD] [CrossRef] [details]
Sreekanth, A., Kala, U. L., Nayar, C. R. & Kurup, M. R. P. (2004). Polyhedron, 23, 41-47.  [ISI] [CSD] [CrossRef] [ChemPort]
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [ISI] [CrossRef] [ChemPort] [details]


Acta Cryst (2013). E69, o586-o587   [ doi:10.1107/S1600536813007617 ]

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