(E)-Ethyl N′-(3-hy­droxy­benzyl­idene)hydrazinecarboxyl­ate dihydrate

Hu, X.-C.; Zhang, J.; Yang, D.-Y.; Lv, L.-P.

doi:10.1107/S1600536811025104

Volume 67
Part 8
Page o1884
August 2011

Received 23 June 2011
Accepted 26 June 2011
Online 2 July 2011

Key indicators
Single-crystal X-ray study
T = 223 K
Mean (C-C) = 0.003 Å
R = 0.043
wR = 0.126
Data-to-parameter ratio = 14.1
Details

(E)-Ethyl N'-(3-hydroxybenzylidene)hydrazinecarboxylate dihydrate

Xian-Chao Hu,^a,^b ^* Jie Zhang,^a Da-Yong Yang ^c and Lu-Ping Lv ^d

^aCollege of Chemical Engineering and Materials Science, Zhejiang University of Technology, Hangzhou 310014, People's Republic of China,^bResearch Center of Analysis and Measurement, Zhejiang University of Technology, Hangzhou 310014, People's Republic of China,^cHangzhou Fist Chemical Co. Ltd, Xiaoshan, Hangzhou 310007, People's Republic of China, and ^dLinjiang College, Hangzhou Vocational and Technical College, Hangzhou 310018, People's Republic of China
Correspondence e-mail: zgdhxc@126.com

The asymmetric unit of the title compound, C₁₀H₁₂N₂O₃·2H₂O, contains two organic molecules with similar conformations and four water molecules. Each organic molecule is close to planar (r.m.s. deviations = 0.035 and 0.108 Å) and adopts a trans conformation with respect to its C=N bond. In the crystal, the components are linked into a three-dimensional network by N-HO, O-HO, O-HN and C-HO hydrogen bonds, some of which are bifurcated. An R₂²(8) loop occurs between adjacent organic molecules.

Related literature

For general background to benzaldehydehydrazone derivatives, see: Parashar et al. (1988); Hadjoudis et al. (1987); Borg et al. (1999). For a related structure, see: Shang et al. (2007).

Experimental

Crystal data

C₁₀H₁₂N₂O₃·2H₂O
M_r = 244.25
Monoclinic, P 2₁ /c
a = 12.8074 (10) Å
b = 21.9101 (18) Å
c = 8.9048 (7) Å
= 96.490 (3)°
V = 2482.8 (3) Å³
Z = 8
Mo K radiation
= 0.11 mm^-1
T = 223 K
0.20 × 0.19 × 0.18 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2002) T_min = 0.977, T_max = 0.989
22432 measured reflections
4819 independent reflections
3377 reflections with I > 2(I)
R_int = 0.036

Refinement

R[F² > 2(F²)] = 0.043
wR(F²) = 0.126
S = 0.95
4819 reflections
341 parameters
H atoms treated by a mixture of independent and constrained refinement
_max = 0.16 e Å^-3
_min = -0.14 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N2-H2O6ⁱ	0.86	2.29	3.0968 (18)	157
N4-H4NO3	0.86	2.24	3.0849 (18)	167
O6-H6O4W	0.82	1.90	2.675 (2)	157
C3-H3O5	0.93	2.51	3.422 (2)	168
O1W-H1AO2Wⁱⁱ	0.84 (3)	2.04 (3)	2.874 (3)	178 (3)
O1W-H1BO2Wⁱⁱⁱ	0.91 (3)	1.99 (3)	2.906 (2)	177 (3)
O2W-H2AO4	0.91 (3)	2.02 (3)	2.899 (2)	163 (2)
O2W-H2BO1^iv	0.85 (3)	2.25 (3)	2.9268 (19)	136 (2)
O2W-H2BN1^iv	0.85 (3)	2.41 (3)	3.165 (2)	148 (2)
O3W-H3AO4ⁱⁱⁱ	0.89 (3)	2.27 (3)	2.9417 (19)	132 (2)
O3W-H3AN3ⁱⁱⁱ	0.89 (3)	2.38 (3)	3.200 (2)	153 (3)
O3W-H3BO1	0.90 (3)	2.10 (3)	2.991 (2)	171 (3)
O4W-H4BO3W^v	0.98 (6)	1.84 (6)	2.819 (3)	173 (5)
O4W-H4AO3W^iv	0.81 (3)	2.15 (3)	2.955 (2)	169 (3)
Symmetry codes: (i) x-1, y, z+1; (ii) -x+1, -y+1, -z+1; (iii) $[-x+1, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (iv) $[-x+1, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (v) $[x+1, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

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: HB5929 ).

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.
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