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Volume 69 
Part 7 
Pages o1160-o1161  
July 2013  

Received 5 June 2013
Accepted 20 June 2013
Online 26 June 2013

Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.003 Å
R = 0.053
wR = 0.176
Data-to-parameter ratio = 15.4
Details
Open access

N'-[(E)-4-Benzyloxy-2-hydroxybenzylidene]-4-nitrobenzohydrazide dimethylformamide monosolvate

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, C21H17N3O5·C3H7NO, exists in an E conformation with respect to the azomethine double bond of the hydrazide molecule. This molecule contains an intramolecular O-H...N hydrogen bond, while an intermolecular N-H...O hydrogen bond links the hydrazide to the formamide molecule of solvation. Nonclassical C-H...O intermolecular hydrogen bonds build up a supramolecular architecture, together with two C-H...[pi] interactions and a weak [pi]-[pi] interaction, with a centroid-centroid distance of 3.650 (13) Å.

Related literature

For the biological and analytical applications of carbohydrazides, see: Vicini et al. (2002[Vicini, P., Zani, F., Cozzini, P. & Doytchinova, I. (2002). Eur. J. Med. Chem. 37, 553-564.]); Savini et al. (2002[Savini, L., Chiasserini, L., Gaeta, A. & Pellerano, C. (2002). Bioorg. Med. Chem. 10, 2193-2198.]); Grande et al. (2007[Grande, F., Aiello, F., Grazia, O. D., Brizzi, A., Garofalo, A. & Neamati, N. (2007). Bioorg. Med. Chem. 15, 288-294.]). For the synthesis of related compounds, see: Mathew & Kurup (2011[Mathew, N. & Kurup, M. R. P. (2011). Spectrochim. Acta Part A, 78, 1424-1428.]); Despaigne et al. (2009[Despaigne, A. A. R., Silva, J. G. D., Carmo, A. C. M. D. & Piro, O. E. (2009). Inorg. Chim. Acta, 362, 2117-2122.]). For related structures, see: Joseph et al. (2012[Joseph, B., Sithambaresan, M. & Kurup, M. R. P. (2012). Acta Cryst. E68, o1421-o1422.]).

[Scheme 1]

Experimental

Crystal data
  • C21H17N3O5·C3H7NO

  • Mr = 464.47

  • Monoclinic, P 21 /c

  • a = 10.0160 (8) Å

  • b = 22.661 (2) Å

  • c = 10.2611 (11) Å

  • [beta] = 101.392 (5)°

  • V = 2283.1 (4) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.10 mm-1

  • T = 296 K

  • 0.40 × 0.20 × 0.20 mm

Data collection
  • Bruker Kappa APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2004[Bruker (2004). APEX2, SAINT and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.977, Tmax = 0.981

  • 16107 measured reflections

  • 4910 independent reflections

  • 2901 reflections with I > 2[sigma](I)

  • Rint = 0.031

Refinement
  • R[F2 > 2[sigma](F2)] = 0.053

  • wR(F2) = 0.176

  • S = 1.04

  • 4910 reflections

  • 318 parameters

  • 2 restraints

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

  • [Delta][rho]max = 0.40 e Å-3

  • [Delta][rho]min = -0.22 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C1-C6 ring.

D-H...A D-H H...A D...A D-H...A
N2-H2'...O6 0.88 (1) 1.95 (1) 2.810 (3) 166 (2)
O2-H2O...N1 0.85 (1) 1.82 (2) 2.583 (2) 149 (3)
C7-H7B...O3i 0.97 2.49 3.167 (3) 127
C13-H13...O1ii 0.93 2.58 3.448 (3) 156
C21-H21...O6 0.93 2.42 3.206 (3) 143
C12-H12...Cg1ii 0.93 2.91 3.673 (2) 140
C17-H17...Cg1i 0.93 2.85 3.630 (3) 142
Symmetry codes: (i) -x+1, -y, -z+1; (ii) -x, -y, -z.

Data collection: APEX2 (Bruker, 2004[Bruker (2004). APEX2, SAINT and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: APEX2 and SAINT (Bruker, 2004[Bruker (2004). APEX2, SAINT and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT and XPREP (Bruker, 2004[Bruker (2004). APEX2, SAINT and XPREP. 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: FJ2634 ).


Acknowledgements

BJ is grateful to the Council for Scientific and Industrial Research, New Delhi, India, for the award of a Senior Research Fellowship. MRPK is grateful to UGC, New Delhi, for a UGC-BSR one-time grant to Faculty. The authors are grateful to Dr Matthias Zeller, Department of Chemistry, Youngstown State University, for the support with data refinement. The authors are grateful to the Sophisticated Analytical Instruments Facility, Cochin University of Science and Technology, Kochi-22, India for the single-crystal X-ray diffraction measurements.

References

Brandenburg, K. (2010). DIAMOND. Crystal Impact GbR, Bonn, Germany.
Bruker (2004). APEX2, SAINT and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA.
Despaigne, A. A. R., Silva, J. G. D., Carmo, A. C. M. D. & Piro, O. E. (2009). Inorg. Chim. Acta, 362, 2117-2122.  [Web of Science] [CSD] [CrossRef] [ChemPort]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Grande, F., Aiello, F., Grazia, O. D., Brizzi, A., Garofalo, A. & Neamati, N. (2007). Bioorg. Med. Chem. 15, 288-294.  [CrossRef] [PubMed] [ChemPort]
Joseph, B., Sithambaresan, M. & Kurup, M. R. P. (2012). Acta Cryst. E68, o1421-o1422.  [CSD] [CrossRef] [ChemPort] [IUCr Journals]
Mathew, N. & Kurup, M. R. P. (2011). Spectrochim. Acta Part A, 78, 1424-1428.
Savini, L., Chiasserini, L., Gaeta, A. & Pellerano, C. (2002). Bioorg. Med. Chem. 10, 2193-2198.  [CrossRef] [PubMed] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Vicini, P., Zani, F., Cozzini, P. & Doytchinova, I. (2002). Eur. J. Med. Chem. 37, 553-564.  [Web of Science] [CrossRef] [PubMed] [ChemPort]
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]


Acta Cryst (2013). E69, o1160-o1161   [ doi:10.1107/S1600536813017091 ]

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