(E)-Ethyl N′-(3,4,5-trimethoxy­benzyl­idene)hydrazinecarboxyl­ate

Lv, L.-P.; Ding, X.-M.; Yu, W.-B.; Li, W.-W.; Hu, X.-C.

doi:10.1107/S1600536808033461

Volume 64
Part 11
Page o2127
November 2008

Received 13 October 2008
Accepted 15 October 2008
Online 18 October 2008

Key indicators
Single-crystal X-ray study
T = 273 K
Mean (C-C) = 0.002 Å
R = 0.035
wR = 0.094
Data-to-parameter ratio = 13.5
Details

(E)-Ethyl N'-(3,4,5-trimethoxybenzylidene)hydrazinecarboxylate

Lu-Ping Lv,^a Xiao-Ming Ding,^a Wen-Bo Yu,^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 molecule of the title compound, C₁₃H₁₈N₂O₅, adopts a trans configuration with respect to the C=N bond. The dihedral angle between the benzene ring and the hydrazinecarboxylic acid plane is 49.75 (5)° and an intramolecular C-HO interaction occurs. In the crystal structure, the molecules are linked into a chain along [010] by N-HO hydrogen bonds, and a C-H [pi] contact further stabilizes the structure.

Related literature

For general background, see: Parashar et al. (1988); Hadjoudis et al. (1987). For a related structure, see: Shang et al. (2007).

Experimental

Crystal data

C₁₃H₁₈N₂O₅
M_r = 282.29
Monoclinic, P 2₁ /c
a = 22.037 (2) Å
b = 4.8782 (5) Å
c = 14.0212 (15) Å
= 108.239 (4)°
V = 1431.5 (3) Å³
Z = 4
Mo K radiation
= 0.10 mm^-1
T = 273 (2) K
0.26 × 0.24 × 0.22 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2002) T_min = 0.965, T_max = 0.968
14449 measured reflections
2520 independent reflections
2108 reflections with I > 2(I)
R_int = 0.029

Refinement

R[F² > 2(F²)] = 0.035
wR(F²) = 0.094
S = 1.03
2520 reflections
186 parameters
H-atom parameters constrained
_max = 0.17 e Å^-3
_min = -0.13 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C4-C9 ring.

D-HA	D-H	HA	DA	D-HA
N2-H2O4ⁱ	0.86	1.98	2.8167 (17)	165
C2-H2AO1	0.96	2.53	3.062 (2)	115
C1-H1CCg1ⁱ	0.96	2.92	3.755 (2)	146
Symmetry code: (i) x, y+1, z.

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: HB2820 ).

Acknowledgements

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

References

Bruker (2002). SADABS, SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Hadjoudis, E., Vittorakis, M. & Moustakali-Mavridis, J. (1987). Tetrahedron, 43, 1345-1360.
Parashar, R. K., Sharma, R. C., Kumar, A. & Mohanm, G. (1988). Inorg. Chim. Acta, 151, 201-208.
Shang, Z.-H., Zhang, H.-L. & Ding, Y. (2007). Acta Cryst. E63, o3394.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.

organic compounds