4-[2-(4-Chloro­phen­yl)hydrazinyl­idene]-3-methyl-1H-pyrazol-5(4H)-one

Fun, H.-K.; Quah, C.K.; Nithinchandra; Kalluraya, B.

doi:10.1107/S1600536811037020

Volume 67
Part 10
Page o2670
October 2011

Received 12 September 2011
Accepted 12 September 2011
Online 17 September 2011

Key indicators
Single-crystal X-ray study
T = 100 K
Mean (C-C) = 0.004 Å
R = 0.063
wR = 0.135
Data-to-parameter ratio = 19.8
Details

4-[2-(4-Chlorophenyl)hydrazinylidene]-3-methyl-1H-pyrazol-5(4H)-one

Hoong-Kun Fun,^a ^*⁺ Ching Kheng Quah,^a ⁺⁺ Nithinchandra ^b and Balakrishna 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, C₁₀H₉ClN₄O, the pyrazole ring [maximum deviation = 0.014 (2) Å] forms a dihedral angle of 7.06 (14)° with the chlorobenzene ring. The molecular conformation is stabilized by an intramolecular N-HO hydrogen bond, which generates an S(6) ring motif. In the crystal, inversion dimers linked by pairs of C-HO hydrogen bonds generate R₂²(16) ring motifs. The dimers are further connected by N-HN hydrogen bonds, thereby forming layers lying parallel to the bc plane.

Related literature

For general background to and applications of pyrazole derivatives, see: Rai & Kalluraya (2006); Rai et al. (2008); Sridhar & Perumal (2003). For standard bond-length data, see: Allen et al. (1987). For graph-set notation, see: Bernstein et al. (1995). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986).

Experimental

Crystal data

C₁₀H₉ClN₄O
M_r = 236.66
Monoclinic, P 2₁ /c
a = 15.8496 (5) Å
b = 3.8184 (1) Å
c = 20.3794 (6) Å
= 123.575 (2)°
V = 1027.59 (5) Å³
Z = 4
Mo K radiation
= 0.35 mm^-1
T = 100 K
0.55 × 0.06 × 0.05 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009) T_min = 0.829, T_max = 0.984
11013 measured reflections
3048 independent reflections
2213 reflections with I > 2(I)
R_int = 0.050

Refinement

R[F² > 2(F²)] = 0.063
wR(F²) = 0.135
S = 1.08
3048 reflections
154 parameters
H atoms treated by a mixture of independent and constrained refinement
_max = 0.47 e Å^-3
_min = -0.49 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1-H1N1O1	0.93 (3)	2.15 (3)	2.841 (3)	131 (3)
N3-H1N3N4ⁱ	0.87 (3)	2.16 (3)	2.983 (3)	158 (3)
C5-H5AO1ⁱⁱ	0.95	2.47	3.334 (3)	151
Symmetry codes: (i) $[-x+2, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (ii) -x+2, -y+1, -z+1.

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); 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, 2009).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB6405 ).

Acknowledgements

HKF and CKQ thank Universiti Sains Malaysia for the Research University Grant (No. 1001/PFIZIK/811160).

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.
Bernstein, J., Davis, R. E., Shimoni, L. & Chamg, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.
Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105-107.
Rai, N. S. & Kalluraya, B. (2006). Indian J. Chem. Sect. B, 46, 375-378.
Rai, N. S., Kalluraya, B., Lingappa, B., Shenoy, S. & Puranic, V. G. (2008). Eur. J. Med. Chem. 43, 1715-1720.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.
Sridhar, R. & Perumal, P. T. (2003). Synth. Commun. 33, 1483-1488.

organic compounds