Ethyl 2-[(Z)-2-benzyl­hydrazin-1-yl­idene]-2-bromo­acetate

Yang, Q.-J.; Liu, D.; Zuo, J.; Hu, G.-D.; Zhao, L.-X.

doi:10.1107/S1600536810032071

Volume 66
Part 9
Page o2334
September 2010

Received 28 July 2010
Accepted 10 August 2010
Online 18 August 2010

Key indicators
Single-crystal X-ray study
T = 294 K
Mean (C-C) = 0.005 Å
R = 0.038
wR = 0.111
Data-to-parameter ratio = 15.0
Details

Ethyl 2-[(Z)-2-benzylhydrazin-1-ylidene]-2-bromoacetate

Qian-Jiao Yang,^a Dan Liu,^a Jian Zuo,^b Guo-Dong Hu ^a and Lin-Xiang Zhao ^a ^*

^aKey Laboratory of Original New Drug Design and Discovery of the Ministry of Education, College of Pharmaceutical Engineering, Shenyang Pharmaceutical University, Shenyang, Liaoning 110016, People's Republic of China, and ^bKey Laboratory of Marine Chemistry Theory and Technology, Ministry of Education, College of Chemistry and Chemical Engineering, Ocean University of China, Qingdao, Shandong 266100, People's Republic of China
Correspondence e-mail: zhaolinxiang@syphu.edu.cn

In the title compound, C₁₁H₁₃BrN₂O₂, the dihedral angle between the phenyl ring and the almost planar (r.m.s. deviation = 0.011 Å) C-C(Br)=N-N(H)- fragment is 74.94 (16)°. In the crystal, molecules are linked by N-HO hydrogen bonds, which generate C(6) chains propagating in [010]. Weak aromatic [pi] - [pi] stacking [centroid-centroid separation = 3.784 (3) Å] may also help to consolidate the packing.

Related literature

For the use of the title compound in the preparation of heterocyclic compounds via the diploar cycloaddition of thiadiazole, see Feddouli et al. (2004); Abouricha et al. (2005); Hafez et al. (2008). For the synthesis of the title compound, see Bach et al. (1994).

Experimental

Crystal data

C₁₁H₁₃BrN₂O₂
M_r = 285.14
Monoclinic, P 2₁ /c
a = 9.046 (1) Å
b = 11.235 (1) Å
c = 12.326 (2) Å
= 92.935 (4)°
V = 1251.1 (3) Å³
Z = 4
Mo K radiation
= 3.27 mm^-1
T = 294 K
0.25 × 0.14 × 0.07 mm

Data collection

Siemens APEX CCD diffractometer
Absorption correction: multi-scan (SADABS; Siemens, 1996) T_min = 0.495, T_max = 0.803
4952 measured reflections
2188 independent reflections
1475 reflections with I > 2(I)
R_int = 0.019

Refinement

R[F² > 2(F²)] = 0.038
wR(F²) = 0.111
S = 1.02
2188 reflections
146 parameters
H-atom parameters constrained
_max = 0.26 e Å^-3
_min = -0.61 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1-H1O1ⁱ	0.86	2.24	2.965 (4)	141
Symmetry code: (i) $[-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB5585 ).

Acknowledgements

This work was supported by the China International Science and Technology Cooperation Plan (2009DEA31200).

References

Abouricha, S., Rakib, E., Benchat, N., Alaoui, M., Allouchi, H. & EI-Bali, B. (2005). Synth. Commun. 35, 2213-2221.
Bach, K. K., El-Seedi, H. R., Jensen, H. M., Nielsen, H. B., Thomsen, I. & Torssell, K. B. G. (1994). Tetrahedron, 50, 7543-7556.
Feddouli, A., Itto, M. Y. A., Hasnaoui, A., Villemin, D., Jaffrs, P. A., Santos, J. S. D. O., Riahi, A., Huet, F. & Daran, J. C. (2004). J. Heterocycl. Chem. 41, 731-735.
Hafez, H. N., Hegab, M. I., Ahmed-Farag, I. S. & EI-Gazzar, A. B. A. (2008). Bioorg. Med. Chem. Lett. 18, 4538-4543.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Siemens (1996). SMART, SAINT and SADABS. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.

organic compounds