N′-[(Z)-4-Methyl­benzyl­idene]-4-nitro­benzohydrazide monohydrate

Fun, H.-K.; Jebas, S.R.; Sujith, K.V.; Kalluraya, B.

doi:10.1107/S1600536808037008

Volume 64
Part 12
Page o2338
December 2008

Received 4 November 2008
Accepted 10 November 2008
Online 13 November 2008

Key indicators
Single-crystal X-ray study
T = 100 K
Mean (C-C) = 0.001 Å
R = 0.037
wR = 0.119
Data-to-parameter ratio = 35.0
Details

N'-[(Z)-4-Methylbenzylidene]-4-nitrobenzohydrazide monohydrate

Hoong-Kun Fun,^a ^* Samuel Robinson Jebas,^a ⁺ K. V. Sujith ^b and B. Kalluraya ^b

^aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and ^bDepartment of Studies in Chemistry, Mangalore University, Mangalagangotri, Mangalore 574 199, India
Correspondence e-mail: hkfun@usm.my

In the title compound, C₁₅H₁₃N₃O₃·H₂O, the two benzene rings form a dihedral angle of 2.03 (2)°. In the crystal structure, adjacent hydrazide molecules are linked into dimers by water molecules; these dimers are then stacked along the b axis. Intermolecular O-HO, O-HN and C-HO hydrogen bonds and a [pi] - [pi] stacking interaction between the nitrobenzene and tolyl rings with a centroid-centroid distance of 3.8208 (3) Å are observed. There is also a short ON contact [2.6824 (7) Å].

Related literature

For related literature on hydrazones, see: Sridhar & Perumal (2003). For the biological applications of hydrazides/hydrazones, see: Bedia et al. (2006). For a related structure, see: Fun et al. (2008). For bond-length data, see: Allen et al. (1987).

Experimental

Crystal data

C₁₅H₁₃N₃O₃·H₂O
M_r = 301.30
Triclinic, $[P \overline 1]$
a = 6.5387 (1) Å
b = 6.9730 (1) Å
c = 15.9064 (3) Å
= 80.524 (1)°
= 82.628 (1)°
= 85.036 (1)°
V = 707.85 (2) Å³
Z = 2
Mo K radiation
= 0.10 mm^-1
T = 100.0 (1) K
0.68 × 0.44 × 0.23 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005) T_min = 0.932, T_max = 0.976
31311 measured reflections
7380 independent reflections
6571 reflections with I > 2(I)
R_int = 0.020

Refinement

R[F² > 2(F²)] = 0.037
wR(F²) = 0.118
S = 1.05
7380 reflections
211 parameters
4 restraints
H atoms treated by a mixture of independent and constrained refinement
_max = 0.48 e Å^-3
_min = -0.59 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N2-H1N2O1W	0.864 (8)	1.978 (9)	2.8191 (7)	164.4 (11)
O1W-H2W1O1ⁱ	0.837 (9)	2.013 (9)	2.8327 (7)	166.1 (11)
O1W-H1W1O1ⁱⁱ	0.851 (9)	2.258 (11)	2.9430 (6)	137.7 (10)
O1W-H1W1N1ⁱⁱ	0.851 (9)	2.357 (9)	3.1287 (7)	151.0 (11)
C1-H1AO1Wⁱⁱⁱ	0.93	2.50	3.4090 (7)	165
C4-H4AO2^iv	0.93	2.58	3.4565 (8)	157
C7-H7AO1W	0.93	2.55	3.2393 (7)	132
Symmetry codes: (i) -x+2, -y+1, -z; (ii) x-1, y, z; (iii) x+1, y, z; (iv) x, y-1, z+1.

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2003).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: IS2358 ).

Acknowledgements

FHK and SRJ thank the Malaysian Government and Universiti Sains Malaysia for the Science Fund grant No. 305/PFIZIK/613312. SRJ thanks Universiti Sains Malaysia for a post-doctoral research fellowship.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.
Bedia, K.-K., Elçin, O., Seda, U., Fatma, K., Nathaly, S., Sevim, R. & Dimoglo, A. (2006). Eur. J. Med. Chem. 41, 1253-1261.
Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Fun, H.-K., Patil, P. S., Jebas, S. R., Sujith, K. V. & Kalluraya, B. (2008). Acta Cryst. E64, o1594-o1595.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2003). J. Appl. Cryst. 36, 7-13.
Sridhar, R. & Perumal, P. T. (2003). Synth. Commun. 33, 1483-1488.

organic compounds