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Volume 68 
Part 11 
Pages o3140-o3141  
November 2012  

Received 24 September 2012
Accepted 5 October 2012
Online 20 October 2012

Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.003 Å
R = 0.046
wR = 0.122
Data-to-parameter ratio = 16.8
Details
Open access

2-(1H-Indol-3-yl)acetohydrazide

aMaterials Chemistry Laboratory, Department of Chemistry, GC University, Lahore 54000, Pakistan,bInterdisciplinary Research Center in Biomedical Materials, COMSATS Institute of Information Technology, Lahore 54000, Pakistan, and cDepartment of Chemistry, University of Otago, PO Box 56, Dunedin, New Zealand
Correspondence e-mail: iuklodhi@yahoo.com

In the title compound C10H11N3O, the mean plane of the indole ring system (r.m.s. deviation 0.0131 Å) subtends a dihedral angle of 87.27 (5)° to the almost planar acetohydrazide substituent (r.m.s. deviation 0.0291 Å). In the crystal, bifurcated N-H...(O,N) and N-H...N hydrogen bonds involving the pyrrole N-H grouping combine to form zigzag chains along a. Additional N-H...O contacts from the hydrazide N-H group augmented by C-H...[pi] interactions link the molecules into chains along the a axis. The overall effect of these contacts is a three-dimensional network structure with molecules stacked along the b-axis direction.

Related literature

For the use of hydrazides in the synthesis of heterocyclic compounds, see: Narayana et al. (2005a[Narayana, B., Ashalatha, B. V., Vijayaraj, K. K., Fernandes, J. & Sarojini, B. K. (2005a). Bioorg. Med. Chem. 13, 4638-4644.],b[Narayana, B., Vijayaraj, K. K., Ashalatha, B. V. & Suchetha Kumari, N. (2005b). Pharmazie, 338, 373-377.]) and in the production of pharmaceuticals, see: Liu et al. (2006[Liu, F., Stephen, A. G., Adainson, C. S., Gousset, K., Aman, M. J., Freed, E. O., Fisher, R. J. & Burke, T. R. Jr (2006). Org. Lett. 8, 5165-5168.]). For related structures, see: Butcher et al. (2007[Butcher, R. J., Jasinski, J. P., Narayana, B., Sunil, K. & Yathirajan, H. S. (2007). Acta Cryst. E63, o3652.]); Hou (2009[Hou, J.-L. (2009). Acta Cryst. E65, o851.]); Li & Ban (2009[Li, C.-M. & Ban, H.-Y. (2009). Acta Cryst. E65, o883.]); Sarojini et al. (2007a[Sarojini, B. K., Yathirajan, H. S., Sunil, K., Narayana, B. & Bolte, M. (2007a). Acta Cryst. E63, o3487.],b[Sarojini, B. K., Narayana, B., Sunil, K., Yathirajan, H. S. & Bolte, M. (2007b). Acta Cryst. E63, o3551.],c[Sarojini, B. K., Narayana, B., Sunil, K., Yathirajan, H. S. & Bolte, M. (2007c). Acta Cryst. E63, o3862-o3863.],d[Sarojini, B. K., Mustafa, K., Narayana, B., Yathirajan, H. S. & Bolte, M. (2007d). Acta Cryst. E63, o4419.]).

[Scheme 1]

Experimental

Crystal data
  • C10H11N3O

  • Mr = 189.22

  • Orthorhombic, P b c a

  • a = 12.1599 (7) Å

  • b = 9.6153 (4) Å

  • c = 16.2345 (8) Å

  • V = 1898.16 (16) Å3

  • Z = 8

  • Mo K[alpha] radiation

  • [mu] = 0.09 mm-1

  • T = 296 K

  • 0.17 × 0.14 × 0.11 mm

Data collection
  • Bruker APEXII CCD area detector diffractometer

  • 8600 measured reflections

  • 2329 independent reflections

  • 1294 reflections with I > 2[sigma](I)

  • Rint = 0.039

Refinement
  • R[F2 > 2[sigma](F2)] = 0.046

  • wR(F2) = 0.122

  • S = 1.00

  • 2329 reflections

  • 139 parameters

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

  • [Delta][rho]max = 0.16 e Å-3

  • [Delta][rho]min = -0.16 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg2 is the centroid of the C1-C6 benzene ring.

D-H...A D-H H...A D...A D-H...A
N1-H1N...O10i 0.80 (2) 2.21 (2) 2.927 (2) 149.4 (19)
N1-H1N...N3i 0.80 (2) 2.50 (2) 3.126 (2) 136.6 (19)
N2-H2N...O10ii 0.89 (2) 2.20 (2) 3.0799 (19) 166.3 (17)
C9-H9A...Cg2iii 0.97 2.73 3.644 (2) 157
Symmetry codes: (i) [x+{\script{1\over 2}}, -y+{\script{1\over 2}}, -z+1]; (ii) [-x+{\script{1\over 2}}, y-{\script{1\over 2}}, z]; (iii) [x, -y-{\script{3\over 2}}, z-{\script{1\over 2}}].

Data collection: APEX2 (Bruker 2005[Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: APEX2 and SAINT (Bruker 2005[Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; 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, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]) and Mercury (Macrae et al., 2008[Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.]); software used to prepare material for publication: SHELXL97, enCIFer (Allen et al., 2004[Allen, F. H., Johnson, O., Shields, G. P., Smith, B. R. & Towler, M. (2004). J. Appl. Cryst. 37, 335-338.]), PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]), 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: HG5253 ).


Acknowledgements

The authors acknowledge the Higher Education Commission of Pakistan for the purchase of the diffractometer.

References

Allen, F. H., Johnson, O., Shields, G. P., Smith, B. R. & Towler, M. (2004). J. Appl. Cryst. 37, 335-338.  [ISI] [CrossRef] [ChemPort] [details]
Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Butcher, R. J., Jasinski, J. P., Narayana, B., Sunil, K. & Yathirajan, H. S. (2007). Acta Cryst. E63, o3652.  [CSD] [CrossRef] [details]
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  [CrossRef] [details]
Hou, J.-L. (2009). Acta Cryst. E65, o851.  [CSD] [CrossRef] [details]
Li, C.-M. & Ban, H.-Y. (2009). Acta Cryst. E65, o883.  [CSD] [CrossRef] [details]
Liu, F., Stephen, A. G., Adainson, C. S., Gousset, K., Aman, M. J., Freed, E. O., Fisher, R. J. & Burke, T. R. Jr (2006). Org. Lett. 8, 5165-5168.  [ISI] [CrossRef] [PubMed] [ChemPort]
Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.  [ISI] [CrossRef] [ChemPort] [details]
Narayana, B., Ashalatha, B. V., Vijayaraj, K. K., Fernandes, J. & Sarojini, B. K. (2005a). Bioorg. Med. Chem. 13, 4638-4644.  [CrossRef] [PubMed] [ChemPort]
Narayana, B., Vijayaraj, K. K., Ashalatha, B. V. & Suchetha Kumari, N. (2005b). Pharmazie, 338, 373-377.  [CrossRef] [ChemPort]
Sarojini, B. K., Mustafa, K., Narayana, B., Yathirajan, H. S. & Bolte, M. (2007d). Acta Cryst. E63, o4419.  [CSD] [CrossRef] [details]
Sarojini, B. K., Narayana, B., Sunil, K., Yathirajan, H. S. & Bolte, M. (2007b). Acta Cryst. E63, o3551.  [CSD] [CrossRef] [details]
Sarojini, B. K., Narayana, B., Sunil, K., Yathirajan, H. S. & Bolte, M. (2007c). Acta Cryst. E63, o3862-o3863.  [CSD] [CrossRef] [details]
Sarojini, B. K., Yathirajan, H. S., Sunil, K., Narayana, B. & Bolte, M. (2007a). Acta Cryst. E63, o3487.  [CSD] [CrossRef] [details]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [ISI] [CrossRef] [ChemPort] [details]


Acta Cryst (2012). E68, o3140-o3141   [ doi:10.1107/S1600536812041694 ]

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