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

Asiri, A.M.; Arshad, M.N.; Zayed, M.E.M.; Alamry, K.A.; Bokhari, T.H.

doi:10.1107/S1600536812046521

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 (C-C) = 0.002 Å
R = 0.040
wR = 0.113
Data-to-parameter ratio = 16.2
Details

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

Abdullah M. Asiri,^a,^b ^* Muhammad Nadeem Arshad,^b Mohie E. M. Zayed,^a Khalid A. Alamry ^a,^b and Tanveer Hussain Bokhari ^c ^*

^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-HO and C-HO 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, 2012).

Experimental

Crystal data

C₁₁H₁₃ClN₂O₂
M_r = 240.68
Monoclinic, P 2₁ /c
a = 4.6152 (1) Å
b = 9.9444 (1) Å
c = 26.3152 (3) Å
= 90.692 (1)°
V = 1207.66 (3) Å³
Z = 4
Cu K radiation
= 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) T_min = 0.692, T_max = 1.000
9526 measured reflections
2436 independent reflections
2224 reflections with I > 2(I)
R_int = 0.019

Refinement

R[F² > 2(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
_max = 0.28 e Å^-3
_min = -0.23 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C6-H6O1ⁱ	0.93	2.52	3.331 (2)	145
N1-H1O1ⁱ	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); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: WinGX (Farrugia, 2012).

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.
Asiri, A. M., Arshad, M. N., Zayed, M. E. M., Alamry, K. A. & Shafiq, M. (2012). Acta Cryst. E68, o3274.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.

organic compounds