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

Sidra, L.R.; Khan, I.U.; Yar, M.; Simpson, J.

doi:10.1107/S1600536812041694

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 (C-C) = 0.003 Å
R = 0.046
wR = 0.122
Data-to-parameter ratio = 16.8
Details

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

Lala Rukh Sidra,^a Islam Ullah Khan,^a ^* Muhammad Yar ^b and Jim Simpson ^c

^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-HN hydrogen bonds involving the pyrrole N-H grouping combine to form zigzag chains along a. Additional N-HO 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,b) and in the production of pharmaceuticals, see: Liu et al. (2006). For related structures, see: Butcher et al. (2007); Hou (2009); Li & Ban (2009); Sarojini et al. (2007a,b,c,d).

Experimental

Crystal data

C₁₀H₁₁N₃O
M_r = 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 radiation
= 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(I)
R_int = 0.039

Refinement

R[F² > 2(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
_max = 0.16 e Å^-3
_min = -0.16 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

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

D-HA	D-H	HA	DA	D-HA
N1-H1NO10ⁱ	0.80 (2)	2.21 (2)	2.927 (2)	149.4 (19)
N1-H1NN3ⁱ	0.80 (2)	2.50 (2)	3.126 (2)	136.6 (19)
N2-H2NO10ⁱⁱ	0.89 (2)	2.20 (2)	3.0799 (19)	166.3 (17)
C9-H9ACg2ⁱⁱⁱ	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); cell refinement: APEX2 and SAINT (Bruker 2005); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL97, enCIFer (Allen et al., 2004), PLATON (Spek, 2009), publCIF (Westrip 2010).

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.
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.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
Hou, J.-L. (2009). Acta Cryst. E65, o851.
Li, C.-M. & Ban, H.-Y. (2009). Acta Cryst. E65, o883.
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.
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.
Narayana, B., Ashalatha, B. V., Vijayaraj, K. K., Fernandes, J. & Sarojini, B. K. (2005a). Bioorg. Med. Chem. 13, 4638-4644.
Narayana, B., Vijayaraj, K. K., Ashalatha, B. V. & Suchetha Kumari, N. (2005b). Pharmazie, 338, 373-377.
Sarojini, B. K., Mustafa, K., Narayana, B., Yathirajan, H. S. & Bolte, M. (2007d). Acta Cryst. E63, o4419.
Sarojini, B. K., Narayana, B., Sunil, K., Yathirajan, H. S. & Bolte, M. (2007b). Acta Cryst. E63, o3551.
Sarojini, B. K., Narayana, B., Sunil, K., Yathirajan, H. S. & Bolte, M. (2007c). Acta Cryst. E63, o3862-o3863.
Sarojini, B. K., Yathirajan, H. S., Sunil, K., Narayana, B. & Bolte, M. (2007a). Acta Cryst. E63, o3487.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.

organic compounds

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

Related literature

Experimental

Crystal data

Data collection

Refinement

Acknowledgements

References