[Journal logo]

Volume 70 
Part 1 
Page o47  
January 2014  

Received 5 December 2013
Accepted 9 December 2013
Online 14 December 2013

Key indicators
Single-crystal X-ray study
T = 102 K
Mean [sigma](C-C) = 0.010 Å
R = 0.059
wR = 0.152
Data-to-parameter ratio = 8.3
Details
Open access

4-Chloro-N'-[(3Z)-2-oxo-2,3-di­hydro-1H-indol-3-yl­idene]benzohydrazide

aChemistry and Environmental Division, Manchester Metropolitan University, Manchester M1 5GD, England,bChemistry Department, Faculty of Science, Minia University, 61519 El-Minia, Egypt,cDepartment of Chemistry, Tulane University, New Orleans, LA 70118, USA,dDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey,eChemistry Department, Faculty of Science, Assiut University, Assiut, Egypt, and fKirkuk University, College of Science, Department of Chemistry, Kirkuk, Iraq
Correspondence e-mail: shaabankamel@yahoo.com

In the title compound, C15H10ClN3O2, the benzene ring is slightly twisted out of the plane of the 2,3-di­hydro-1H-indole ring system (r.m.s. deviation = 0.007 Å), forming a dihedral angle of 7.4 (3)°. An intra­molecular N-H...O hydrogen bond forms a six-membered ring. In the crystal, mol­ecules are linked via N-H...O and C-H...O hydrogen bonds, forming layers alternately perpendicular to [011] and [0-11].

Related literature

For the diverse bio-activities of acid hydrazides and their condensed products, see: Adekunle et al. (2012[Adekunle, F. A. O., Woods, J. A. O. & Odunola, O. A. (2012). Res. J. Pharm. Bio. Chem. Sci., 3, 1120-1127.]); Al-Assar et al. (2002[Al-Assar, F., Zelenin, K. N., Lesiovskaya, E. E., Bezant, I. P. & Chakchir, B. A. (2002). Pharm. Chem. J. 36, 598-603.]); Dharmaraj et al. (2001[Dharmaraj, N., Viswanalhamurthi, P. & Natarajan, K. (2001). Transition Met. Chem. 26, 105-118.]); Jain & Vederas (2004[Jain, R. P. & Vederas, J. C. (2004). Bioorg. Med. Chem. Lett. 14, 3655-3658.]); Jeeworth et al. (2000[Jeeworth, T., Wah, H. L. K., Bhowon, M. G., Ghoorhoo, D. & Babooram, K. (2000). Synth. React. Inorg. Met. Org. Chem. 30, 1023-1038.]); Scozzafava et al. (2001[Scozzafava, A., Menabuoni, L., Mincione, F., Mincione, G. & Supuran, C. T. (2001). Bioorg. Med. Chem. Lett. 11, 575-582.]); Siddappa et al. (2008[Siddappa, K., Reddy, T., Mallikarjun, M. & Reddy, C. V. (2008). Eur. J. Chem. 5, 155-162.]); Strappaghetti et al. (2006[Strappaghetti, G., Brodi, C., Giannaccini, G. & Betti, L. (2006). Bioorg. Med. Chem. Lett. 16, 2575-2579.]).

[Scheme 1]

Experimental

Crystal data
  • C15H10ClN3O2

  • Mr = 299.71

  • Orthorhombic, P c a 21

  • a = 31.0359 (12) Å

  • b = 5.2549 (3) Å

  • c = 7.8730 (4) Å

  • V = 1284.01 (11) Å3

  • Z = 4

  • Cu K[alpha] radiation

  • [mu] = 2.72 mm-1

  • T = 102 K

  • 0.22 × 0.17 × 0.01 mm

Data collection
  • Bruker D8 VENTURE PHOTON 100 CMOS diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2013[Bruker (2013). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.75, Tmax = 0.97

  • 4190 measured reflections

  • 1596 independent reflections

  • 1434 reflections with I > 2[sigma](I)

  • Rint = 0.109

Refinement
  • R[F2 > 2[sigma](F2)] = 0.059

  • wR(F2) = 0.152

  • S = 1.16

  • 1596 reflections

  • 193 parameters

  • 3 restraints

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

  • [Delta][rho]max = 0.30 e Å-3

  • [Delta][rho]min = -0.37 e Å-3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), 478 Friedal pairs (44% coverage)

  • Absolute structure parameter: -0.06 (5)

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H1...O2 0.90 (5) 1.87 (6) 2.685 (9) 151 (4)
N3-H3A...O1i 0.91 1.98 2.798 (8) 149
C11-H11...O1i 0.95 2.55 3.218 (10) 128
C14-H14...O2ii 0.95 2.29 3.233 (9) 172
Symmetry codes: (i) [-x+{\script{1\over 2}}, y-1, z-{\script{1\over 2}}]; (ii) [-x+{\script{1\over 2}}, y+1, z+{\script{1\over 2}}].

Data collection: APEX2 (Bruker, 2013[Bruker (2013). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2013[Bruker (2013). 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 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]); software used to prepare material for publication: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SU2672 ).


Acknowledgements

Manchester Metropolitan University, Tulane University and Erciyes University are gratefully acknowledged for supporting this study. The support of NSF-MRI grant No. 1228232 for the purchase of the diffractometer is also gratefully acknowledged.

References

Adekunle, F. A. O., Woods, J. A. O. & Odunola, O. A. (2012). Res. J. Pharm. Bio. Chem. Sci., 3, 1120-1127.  [ChemPort]
Al-Assar, F., Zelenin, K. N., Lesiovskaya, E. E., Bezant, I. P. & Chakchir, B. A. (2002). Pharm. Chem. J. 36, 598-603.  [ChemPort]
Bruker (2013). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Dharmaraj, N., Viswanalhamurthi, P. & Natarajan, K. (2001). Transition Met. Chem. 26, 105-118.  [Web of Science] [CrossRef] [ChemPort]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Flack, H. D. (1983). Acta Cryst. A39, 876-881.  [CrossRef] [IUCr Journals]
Jain, R. P. & Vederas, J. C. (2004). Bioorg. Med. Chem. Lett. 14, 3655-3658.  [CrossRef] [PubMed] [ChemPort]
Jeeworth, T., Wah, H. L. K., Bhowon, M. G., Ghoorhoo, D. & Babooram, K. (2000). Synth. React. Inorg. Met. Org. Chem. 30, 1023-1038.
Scozzafava, A., Menabuoni, L., Mincione, F., Mincione, G. & Supuran, C. T. (2001). Bioorg. Med. Chem. Lett. 11, 575-582.  [CrossRef] [PubMed] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Siddappa, K., Reddy, T., Mallikarjun, M. & Reddy, C. V. (2008). Eur. J. Chem. 5, 155-162.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Strappaghetti, G., Brodi, C., Giannaccini, G. & Betti, L. (2006). Bioorg. Med. Chem. Lett. 16, 2575-2579.  [CrossRef] [PubMed] [ChemPort]


Acta Cryst (2014). E70, o47  [ doi:10.1107/S1600536813033345 ]

This is an open-access article distributed under the terms of the Creative Commons Attribution Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.