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Volume 68 
Part 12 
Page o3274  
December 2012  

Received 18 October 2012
Accepted 25 October 2012
Online 3 November 2012

Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.004 Å
R = 0.038
wR = 0.109
Data-to-parameter ratio = 11.5
Details
Open access

Ethyl (Z)-2-chloro-2-[2-(4-methoxyphenyl)hydrazin-1-ylidene]acetate

aChemistry Department and the, Center of Excellence for Advanced Materials Research (CEAMR), 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,cChemistry Department, Faculty of Science, King Abdulaziz University, PO Box 80203, Jeddah 21589, Saudi Arabia, and dDepartment of Chemistry, Government College University, 38000, Faisalabad, Pakistan
Correspondence e-mail: aasiri2@kau.edu.sa, hafizshafique@hotmail.com

The molecule of the title compound, C11H13ClN2O3, is planar (r.m.s. deviation = 0.0587 Å for non-H atoms) and adopts a Z conformation about the C=N double bond. In the crystal, molecules are linked via an N-H...O hydrogen bond, forming zigzag chains propagating along [010]. These chains are consolidated by C-H...O hydrogen bonds.

Related literature

For closely related structures, see: Asiri et al. (2011a[Asiri, A. M., Al-Youbi, A. O., Zayed, M. E. M. & Ng, S. W. (2011a). Acta Cryst. E67, o1961.],b[Asiri, A. M., Al-Youbi, A. O., Zayed, M. E. M. & Ng, S. W. (2011b). Acta Cryst. E67, o1964.]). For graph-set notation, see: Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]).

[Scheme 1]

Experimental

Crystal data
  • C11H13ClN2O3

  • Mr = 256.68

  • Monoclinic, P 21

  • a = 4.7480 (2) Å

  • b = 9.9256 (4) Å

  • c = 13.3084 (4) Å

  • [beta] = 91.468 (3)°

  • V = 626.98 (4) Å3

  • Z = 2

  • Cu K[alpha] radiation

  • [mu] = 2.71 mm-1

  • T = 296 K

  • 0.23 × 0.11 × 0.06 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, Oxfordshire, England.]) Tmin = 0.860, Tmax = 1.000

  • 3153 measured reflections

  • 1824 independent reflections

  • 1685 reflections with I > 2[sigma](I)

  • Rint = 0.018

Refinement
  • R[F2 > 2[sigma](F2)] = 0.038

  • wR(F2) = 0.109

  • S = 1.07

  • 1824 reflections

  • 159 parameters

  • 1 restraint

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

  • [Delta][rho]max = 0.16 e Å-3

  • [Delta][rho]min = -0.20 e Å-3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), 466 Friedel pairs

  • Flack parameter: 0.01 (2)

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H1N...O2i 0.97 (4) 2.11 (4) 3.053 (3) 164 (3)
C6-H6...O2i 0.93 2.59 3.368 (3) 141
Symmetry code: (i) [-x+2, y-{\script{1\over 2}}, -z+1].

Data collection: CrysAlis PRO (Agilent, 2012[Agilent (2012). CrysAlis PRO. Agilent Technologies, Yarnton, Oxfordshire, 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: SU2515 ).


Acknowledgements

We would like to 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, Oxfordshire, England.
Asiri, A. M., Al-Youbi, A. O., Zayed, M. E. M. & Ng, S. W. (2011a). Acta Cryst. E67, o1961.  [CrossRef] [details]
Asiri, A. M., Al-Youbi, A. O., Zayed, M. E. M. & Ng, S. W. (2011b). Acta Cryst. E67, o1964.  [CSD] [CrossRef] [details]
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.  [CrossRef] [ChemPort] [ISI]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Flack, H. D. (1983). Acta Cryst. A39, 876-881.  [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]


Acta Cryst (2012). E68, o3274  [ doi:10.1107/S1600536812044285 ]

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