N′-(4-Chloro­benzyl­idene)furan-2-carbohydrazide monohydrate

Jiang, J.-H.

doi:10.1107/S1600536810005532

Volume 66
Part 3
Page o627
March 2010

Received 21 January 2010
Accepted 10 February 2010
Online 13 February 2010

Key indicators
Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.005 Å
R = 0.045
wR = 0.145
Data-to-parameter ratio = 16.4
Details

N'-(4-Chlorobenzylidene)furan-2-carbohydrazide monohydrate

Jin-He Jiang ^a ^*

^aMicroscale Science Institute, Department of Chemistry and Chemical Engineering, Weifang University, Weifang 261061, People's Republic of China
Correspondence e-mail: weifangjjh@126.com

In the title compound, C₁₂H₉ClN₂O₂·H₂O, the dihedral angle between the aromatic rings is 13.9 (2)° and an intramolecular N-HO hydrogen bond occurs. In the crystal structure, the components are linked by N-HO, O-HO and C-HO hydrogen bonds.

Related literature

For background to Schiff bases, see: Cimerman et al. (1997). For a related structure, see: Girgis (2006).

Experimental

Crystal data

C₁₂H₉ClN₂O₂·H₂O
M_r = 266.68
Monoclinic, P 2₁
a = 4.5480 (9) Å
b = 12.423 (3) Å
c = 10.971 (2) Å
= 91.90 (3)°
V = 619.5 (2) Å³
Z = 2
Mo K radiation
= 0.31 mm^-1
T = 293 K
0.25 × 0.20 × 0.18 mm

Data collection

Bruker SMART CCD diffractometer
5979 measured reflections
2799 independent reflections
1708 reflections with I > 2(I)
R_int = 0.042

Refinement

R[F² > 2(F²)] = 0.045
wR(F²) = 0.145
S = 1.04
2799 reflections
171 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
_max = 0.23 e Å^-3
_min = -0.34 e Å^-3
Absolute structure: Flack (1983), 1319 Friedel pairs
Flack parameter: 0.01 (11)

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O1W-H1WO1ⁱ	0.97 (5)	1.90 (5)	2.865 (4)	174 (5)
O1W-H2WO1ⁱⁱ	0.92 (6)	1.97 (6)	2.873 (4)	168 (5)
N1-H1AO2	0.86	2.36	2.715 (4)	106
N1-H1AO1W	0.86	2.05	2.886 (4)	165
C8-H8AO1W	0.93	2.49	3.290 (5)	144
Symmetry codes: (i) $[-x, y-{\script{1\over 2}}, -z+2]$ ; (ii) $[-x-1, y-{\script{1\over 2}}, -z+2]$ .

Data collection: SMART (Bruker 1997); cell refinement: SAINT (Bruker 1997); 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: HB5316 ).

References

Bruker (1997). SMART, SAINT and SADABS. Bruker AXS, Inc., Madison, Wisconsin, USA.
Cimerman, Z., Galic, N. & Bosner, B. (1997). Anal. Chim. Acta, 343, 145-153.
Flack, H. D. (1983). Acta Cryst. A39, 876-881.
Girgis, A. S. (2006). J. Chem. Res. pp. 81-85.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.

organic compounds