(E)-Methyl N′-[1-(4-methyl­phen­yl)ethyl­idene]hydrazinecarboxyl­ate

Lv, L.-P.; Yu, W.-B.; Wang, F.; Li, W.-W.; Hu, X.-C.

doi:10.1107/S160053680803184X

Volume 64
Part 11
Page o2071
November 2008

Received 1 October 2008
Accepted 2 October 2008
Online 4 October 2008

Key indicators
Single-crystal X-ray study
T = 273 K
Mean (C-C) = 0.004 Å
R = 0.057
wR = 0.172
Data-to-parameter ratio = 14.1
Details

(E)-Methyl N'-[1-(4-methylphenyl)ethylidene]hydrazinecarboxylate

Lu-Ping Lv,^a Wen-Bo Yu,^a Feng Wang,^a Wei-Wei Li ^a and Xian-Chao Hu ^b ^*

^aDepartment of Chemical Engineering, Hangzhou Vocational and Technical College, Hangzhou 310018, People's Republic of China, and ^bResearch Center of Analysis and Measurement, Zhejiang University of Technology, Hangzhou 310014, People's Republic of China
Correspondence e-mail: zgdhxc@126.com

The title molecule, C₁₁H₁₄N₂O₂, adopts a trans configuration with respect to the C=N bond. The dihedral angle between the benzene ring and the hydrazinecarboxylate plane is 7.61 (16)°. In the crystal structure, molecules are linked into centrosymmetric dimers by N-HO hydrogen bonds and the dimers are linked together by C-H [pi] interactions.

Related literature

For general background, see: Parashar et al. (1988); Hadjoudis et al. (1987); Borg et al. (1999). For a related structure, see Lv et al. (2008).

Experimental

Crystal data

C₁₁H₁₄N₂O₂
M_r = 206.24
Monoclinic, P 2₁ /c
a = 11.5197 (3) Å
b = 5.5734 (6) Å
c = 17.3281 (2) Å
= 94.193 (14)°
V = 1109.55 (12) Å³
Z = 4
Mo K radiation
= 0.09 mm^-1
T = 273 (2) K
0.24 × 0.22 × 0.20 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2002) T_min = 0.978, T_max = 0.980
5502 measured reflections
1951 independent reflections
1209 reflections with I > 2(I)
R_int = 0.032

Refinement

R[F² > 2(F²)] = 0.057
wR(F²) = 0.172
S = 1.03
1951 reflections
138 parameters
3 restraints
H-atom parameters constrained
_max = 0.28 e Å^-3
_min = -0.26 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N2-H2AO1ⁱ	0.86	2.12	2.944 (3)	162
C2-H2Cg1ⁱⁱ	0.93	2.83	3.538 (3)	134
Symmetry codes: (i) -x, -y, -z+1; (ii) $[-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ . Cg1 is the centroid of the C2-C7 benzene ring.

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); 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: CV2459 ).

Acknowledgements

The authors thank Hangzhou Vocational and Technical College, China, for financial support.

References

Borg, S., Vollinga, R. C., Labarre, M., Payza, K., Terenius, L. & Luthman, K. (1999). J. Med. Chem. 42, 4331-4342.
Bruker (2002). SADABS, SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Hadjoudis, E., Vittorakis, M. & Moustakali-Mavridis, J. (1987). Tetrahedron, 43, 1345-1360.
Lv, L.-P., Yu, W.-P., Yu, W.-B., Zhou, X.-F. & Hu, X.-C. (2008). Acta Cryst. E64, o1676.
Parashar, R. K., Sharma, R. C., Kumar, A. & Mohanm, G. (1988). Inorg. Chim. Acta, 151, 201-208.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.

organic compounds