(E)-4-{[2-(2-Furylcarbon­yl)hydrazinyl­idene]meth­yl}-2-meth­oxy­phenyl acetate

Xu, J.; Yue, X.

doi:10.1107/S1600536811008932

Volume 67
Part 4
Page o880
April 2011

Received 4 March 2011
Accepted 9 March 2011
Online 15 March 2011

Key indicators
Single-crystal X-ray study
T = 296 K
Mean (C-C) = 0.002 Å
R = 0.037
wR = 0.105
Data-to-parameter ratio = 18.1
Details

(E)-4-{[2-(2-Furylcarbonyl)hydrazinylidene]methyl}-2-methoxyphenyl acetate

Jun Xu ^a ^* and Xiao-yu Yue ^a

^aDepartment of Quality Detection and Management, Zhengzhou College of Animal Husbandry Engineering, Zhengzhou 450011, People's Republic of China
Correspondence e-mail: xujun20101996@yahoo.com.cn

The molecule of the title Schiff base compound, C₁₅H₁₄N₂O₅, was obtained from a condensation reaction of 4-acetoxy-3-methoxybenzaldehyde and 2-furylcarbonylhydrazide. In the molecule, the furyl ring makes a dihedral angle of 14.63 (10)° with the benzene ring. In the crystal, intermolecular N-HO hydrogen bonds link the molecules into chains along the b axis. Futhermore, weak C-HO interactions connect the chains, forming corrugated layers parallel to (001). The dihedral angle between the rings is 14.63 (10)°.

Related literature

Several phenylhydrazone derivatives have been shown to be potentially DNA-damaging and are mutagenic agents, see: Okabe et al. (1993). For bond lengths and angles in other hydrazone derivatives, see: Bakir & Gyles (2003); Baughman et al. (2004); Ohba (1996); Yao & Jing (2007).

Experimental

Crystal data

C₁₅H₁₄N₂O₅
M_r = 302.28
Orthorhombic, P 2₁ 2₁ 2₁
a = 4.9987 (2) Å
b = 13.4200 (5) Å
c = 21.5876 (8) Å
V = 1448.15 (10) Å³
Z = 4
Mo K radiation
= 0.11 mm^-1
T = 296 K
0.21 × 0.19 × 0.18 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 1998) T_min = 0.973, T_max = 0.977
39211 measured reflections
3626 independent reflections
2988 reflections with I > 2(I)
R_int = 0.037

Refinement

R[F² > 2(F²)] = 0.037
wR(F²) = 0.105
S = 1.04
3626 reflections
200 parameters
H-atom parameters constrained
_max = 0.17 e Å^-3
_min = -0.12 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1-H1AO2ⁱ	0.86	2.25	2.9414 (18)	137
C1-H1BO2ⁱⁱ	0.93	2.38	3.217 (2)	149
Symmetry codes: (i) x-1, y, z; (ii) $[-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL; molecular graphics: XP in SHELXTL, ORTEPIII (Burnett & Johnson, 1996) and PLATON (Spek, 2009); software used to prepare material for publication: SHELXTL.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: DN2664 ).

References

Bakir, M. & Gyles, C. (2003). J. Mol. Struct. 649, 133-135.
Baughman, R. G., Martin, K. L., Singh, R. K. & Stoffer, J. O. (2004). Acta Cryst. C60, o103-o106.
Bruker (1998). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Burnett, M. N. & Johnson, C. K. (1996). ORTEPIII. Report ORNL-6895. Oak Ridge National Laboratory, Tennessee, USA.
Ohba, S. (1996). Acta Cryst. C52, 2118-2119.
Okabe, N., Nakamura, T. & Fukuda, H. (1993). Acta Cryst. C49, 1678-1680.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.
Yao, X.-L. & Jing, Z.-L. (2007). Acta Cryst. E63, o3900.

organic compounds