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Volume 68 
Part 12 
Page o3420  
December 2012  

Received 4 November 2012
Accepted 10 November 2012
Online 24 November 2012

Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.002 Å
R = 0.040
wR = 0.113
Data-to-parameter ratio = 16.2
Details
Open access

(Z)-Ethyl 2-chloro-2-[2-(4-methylphenyl)hydrazinylidene]acetate

aChemistry Department, Faculty of Science, King Abdulaziz University, PO Box 80203, Jeddah 21589, Saudi Arabia,bCenter of Excellence for Advanced Materials Research (CEAMR), Faculty of Science, King Abdulaziz University, PO Box 80203, Jeddah 21589, Saudi Arabia, and cDepartment of Chemistry, Government College University, Faisalabad 38000, Pakistan
Correspondence e-mail: aasiri2@kau.edu.sa, sthbukhari@yahoo.co.uk

The molecule of the title compound, C11H13ClN2O2, is approximately planar (r.m.s. deviation = 0.099 Å for non-H atoms) and adopts a Z conformation about the C=N double bond. In the crystal, molecules are linked by N-H...O and C-H...O hydrogen bonds to the same O-atom acceptor, forming zigzag chains propagating along [010]. These interactions give rise to R21(6) loops.

Related literature

For related structures, see: Asiri et al. (2011[Asiri, A. M., Al-Youbi, A. O., Zayed, M. E. M. & Ng, S. W. (2011). Acta Cryst. E67, o1964.], 2012[Asiri, A. M., Arshad, M. N., Zayed, M. E. M., Alamry, K. A. & Shafiq, M. (2012). Acta Cryst. E68, o3274.]).

[Scheme 1]

Experimental

Crystal data
  • C11H13ClN2O2

  • Mr = 240.68

  • Monoclinic, P 21 /c

  • a = 4.6152 (1) Å

  • b = 9.9444 (1) Å

  • c = 26.3152 (3) Å

  • [beta] = 90.692 (1)°

  • V = 1207.66 (3) Å3

  • Z = 4

  • Cu K[alpha] radiation

  • [mu] = 2.71 mm-1

  • T = 296 K

  • 0.41 × 0.14 × 0.13 mm

Data collection
  • Agilent SuperNova (Dual, Cu at zero, Atlas) CCD diffractometer

  • Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012[Agilent (2012). CrysAlis PRO. Agilent Technologies, Yarnton, England.]) Tmin = 0.692, Tmax = 1.000

  • 9526 measured reflections

  • 2436 independent reflections

  • 2224 reflections with I > 2[sigma](I)

  • Rint = 0.019

Refinement
  • R[F2 > 2[sigma](F2)] = 0.040

  • wR(F2) = 0.113

  • S = 1.06

  • 2436 reflections

  • 150 parameters

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

  • [Delta][rho]max = 0.28 e Å-3

  • [Delta][rho]min = -0.23 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C6-H6...O1i 0.93 2.52 3.331 (2) 145
N1-H1...O1i 0.85 (2) 2.30 (2) 3.1120 (18) 161 (2)
Symmetry code: (i) [-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}].

Data collection: CrysAlis PRO (Agilent, 2012[Agilent (2012). CrysAlis PRO. Agilent Technologies, Yarnton, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; 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: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: WinGX (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB6984 ).


Acknowledgements

The authors thank the Deanship of Scientific Research at King Abdulaziz University for the support of this research via a Research Group Track Grant (No. 3-102/428).

References

Agilent (2012). CrysAlis PRO. Agilent Technologies, Yarnton, England.
Asiri, A. M., Al-Youbi, A. O., Zayed, M. E. M. & Ng, S. W. (2011). Acta Cryst. E67, o1964.  [CSD] [CrossRef] [details]
Asiri, A. M., Arshad, M. N., Zayed, M. E. M., Alamry, K. A. & Shafiq, M. (2012). Acta Cryst. E68, o3274.  [CrossRef] [details]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]


Acta Cryst (2012). E68, o3420  [ doi:10.1107/S1600536812046521 ]

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