4-[3,4-Dimethyl-1-(4-methyl­phen­yl)-5-oxo-4,5-dihydro-1H-pyrazol-4-yl]-3,4-dimethyl-1-(4-methyl­phen­yl)-4,5-dihydro-1H-pyrazol-5-one

Wardell, S.M.S.V.; Howie, A.H.; Tiekink, E.R.T.; Wardell, J.L.

doi:10.1107/S1600536812009208

Volume 68
Part 4
Pages o992-o993
April 2012

Received 1 March 2012
Accepted 1 March 2012
Online 10 March 2012

Key indicators
Single-crystal X-ray study
T = 120 K
Mean (C-C) = 0.002 Å
R = 0.042
wR = 0.136
Data-to-parameter ratio = 17.2
Details

4-[3,4-Dimethyl-1-(4-methylphenyl)-5-oxo-4,5-dihydro-1H-pyrazol-4-yl]-3,4-dimethyl-1-(4-methylphenyl)-4,5-dihydro-1H-pyrazol-5-one

Solange M. S. V. Wardell,^a Alan H. Howie,^b Edward R. T. Tiekink ^c ^* and James L. Wardell ^d ⁺

^aCHEMSOL, 1 Harcourt Road, Aberdeen, AB15 5NY, Scotland,^bDepartment of Chemistry, University of Aberdeen, Meston Walk, Old Aberdeen, AB24 3UE, Scotland,^cDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia, and ^dCentro de Desenvolvimento Tecnológico em Saúde (CDTS), Fundação Oswaldo Cruz (FIOCRUZ), Casa Amarela, Campus de Manguinhos, Av. Brasil 4365, 21040-900, Rio de Janeiro, RJ, Brazil
Correspondence e-mail: Edward.Tiekink@gmail.com

In the title compound, C₂₄H₂₆N₄O₂, the complete molecule is generated by the application of twofold symmetry. The pyrazole ring is approximately planar [r.m.s. deviation = 0.026 Å] and the benzene ring is twisted out of this plane [dihedral angle = 21.94 (7)°]. A twist in the molecule about the central C-C bond [1.566 (3) Å] is also evident [C-C-C-C torsion angle = 44.30 (14)°]. Supramolecular layers in the bc plane are formed in the crystal packing via C-HO and C-H [pi] interactions.

Related literature

For the therapeutic importance of pyrazole compounds, see: Sil et al. (2005); Haddad et al. (2004). For the diverse pharmacological activities of pyrazole compounds, see: Bekhit et al. (2010, 2012); Higashi et al. (2006). For synthetic background, see: Nef (1891): Veibel & Westöö (1953); Katritzky et al. (1997); Wardell et al. (2007); de Lima et al. (2010). For the synthesis of the title compound, see: Bernstein et al. (1947); Gryazeva & Golomolzin (2003).

Experimental

Crystal data

C₂₄H₂₆N₄O₂
M_r = 402.50
Monoclinic, C 2/c
a = 23.0007 (8) Å
b = 6.6712 (2) Å
c = 13.5967 (5) Å
= 92.566 (2)°
V = 2084.22 (12) Å³
Z = 4
Mo K radiation
= 0.08 mm^-1
T = 120 K
0.48 × 0.36 × 0.18 mm

Data collection

Rigaku Saturn724+ diffractometer
Absorption correction: multi-scan (CrystalClear-SM Expert; Rigaku, 2011) T_min = 0.668, T_max = 0.746
11383 measured reflections
2384 independent reflections
1856 reflections with I > 2(I)
R_int = 0.042

Refinement

R[F² > 2(F²)] = 0.042
wR(F²) = 0.136
S = 0.83
2384 reflections
139 parameters
H-atom parameters constrained
_max = 0.26 e Å^-3
_min = -0.18 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C6-C11 ring.

D-HA	D-H	HA	DA	D-HA
C4-H4BO1ⁱ	0.98	2.60	3.5676 (16)	169
C4-H4ACg1ⁱⁱ	0.98	2.82	3.6644 (15)	145
Symmetry codes: (i) $[x, -y+1, z-{\script{1\over 2}}]$ ; (ii) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z-{\script{1\over 2}}]$ .

Data collection: CrystalClear-SM Expert (Rigaku, 2011); cell refinement: CrystalClear-SM Expert; data reduction: CrystalClear-SM Expert; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2006); software used to prepare material for publication: publCIF (Westrip, 2010).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HG5185 ).

Acknowledgements

The use of the EPSRC X-ray crystallographic service at the University of Southampton, England, and the valuable assistance of the staff there is gratefully acknowledged. JLW acknowledges support from CAPES (Brazil). Support from the Ministry of Higher Education, Malaysia, High-Impact Research scheme (UM.C/HIR/MOHE/SC/12) is gratefully acknowledged.

References

Bekhit, A. A., Hymete, A., Asfaw, H., Bekhit, A. & El-D, A. (2012). Arch. Pharm. 345, 147-154.
Bekhit, A. A., Hymete, A., Bekhit, A., El-D, A., Damtew, A. & Aboul-Enein, H. Y. (2010). Mini Rev. Med. Chem. 10, 1014-1033.
Bernstein, J., Stearns, B., Dexter, M. & Lott, W. A. (1947). J. Am. Chem. Soc. 69, 1147-1150.
Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
Gryazeva, O. V. & Golomolzin, B. V. (2003). Chem. Heterocycl. Compd, 39, 1478-1486.
Haddad, N., Salvango, A. & Busacca, C. (2004). Tetrahedron Lett. 45, 5935-5937.
Higashi, Y., Jitsuili, D., Chayama, K. & Yoshizumi, M. (2006). Rec. Pat. Cardiovasc. Drug Dis., 1, 85-93.
Katritzky, A. R., Barczynski, P. & Ostercamp, D. L. (1997). J. Chem. Soc. Perkin Trans II. pp. 969-975.
Lima, G. M. de, Wardell, J. L. & Wardell, S. M. S. V. (2010). J. Chem. Crystallogr. 40, 213-221.
Nef, J. U. (1891). Justus Liebigs Ann. Chem. 266, 62.
Rigaku (2011). CrystalClear-SM Expert. Rigaku Corporation, Tokyo, Japan.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Sil, D., Kumar, R., Sharon, A., Maulik, P. R. & Rama, V. J. (2005). Tetrahedron Lett. 46, 3807-3809.
Veibel, S. & Westöö, G. (1953). Acta Chem. Scand. 7, 119-127.
Wardell, J. L., Skakle, J. M. S., Low, J. N. & Glidewell, C. (2007). Acta Cryst. C63, o462-o467.
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.

organic compounds