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Volume 69 
Part 1 
Page o115  
January 2013  

Received 5 December 2012
Accepted 14 December 2012
Online 19 December 2012

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.003 Å
Disorder in main residue
R = 0.055
wR = 0.154
Data-to-parameter ratio = 14.3
Details
Open access

A second monoclinic polymorph of 4-[(E)-(4-benzyloxybenzylidene)amino]-1,5-dimethyl-2-phenyl-1H-pyrazol-3(2H)-one

aX-ray Crystallography Laboratory, Post-Graduate Department of Physics & Electronics, University of Jammu, Jammu Tawi 180 006, India,bDepartment of Studies in Chemistry, Mangalore University, Mangalagangotri 574 199, India, and cDepartment of Chemistry, P.A. College of Engineering, Nadupadavu, Mangalore 574 153, India
Correspondence e-mail: rkvk.paper11@gmail.com

In the title compound, C25H23N3O2, the central benzene ring makes dihedral angles of 77.14 (8) and 87.7 (2)° with the terminal benzene rings and an angle of 1.9 (1)° with the pyrazolone ring. The benzene ring and the N atom of the pyrazole ring bearing the phenyl substituent are disordered over two sets of sites with an occupancy ratio of 0.71 (2):0.29 (2). The N atoms of the pyrazole ring have a pyramidal environment, the sums of the valence angles around them being 354.6 (3) and 352.0 (6)/349.5 (15)°. In the crystal, molecules are packed into layers parallel to the ac plane. The other monoclinic polymorphic form was reported recently [Dutkiewicz et al. (2012[Dutkiewicz, G., Shetty, D. N., Narayana, B., Yathirajan, H. S. & Kubicki, M. (2012). Acta Cryst. E68, o1324.]). Acta Cryst. E68, o1324].

Related literature

For potential applications of Schiff bases, see: Patole et al. (2006[Patole, J., Shingnapurkar, D., Padhyea, S. & Ratledge, C. (2006). Bioorg. Med. Chem. Lett. 16, 1514-1517.]); Shi et al.(2007[Shi, L., Ge, H., Tan, S., Li, H., Song, Y., Zhu, H. & Tan, R. (2007). Eur. J. Med. Chem. 42, 558-564.]); Satyanarayana et al. (2008[Satyanarayana, V. S. V., Sreevani, P., Sivakumar, A. & Vijayakumar, V. (2008). Arkivoc, 17, 221-233.]). For related structures, see: Liu et al.(2008[Liu, S.-X., Tian, X., Zhen, X.-L., Li, Z.-C. & Han, J.-R. (2008). Acta Cryst. E64, o2245.]); Hu, (2006[Hu, T.-P. (2006). Acta Cryst. E62, o2270-o2271.]). For the other monoclinic polymorph, see Dutkiewicz et al., (2012[Dutkiewicz, G., Shetty, D. N., Narayana, B., Yathirajan, H. S. & Kubicki, M. (2012). Acta Cryst. E68, o1324.]).

[Scheme 1]

Experimental

Crystal data
  • C25H23N3O2

  • Mr = 397.46

  • Monoclinic, P 21 /n

  • a = 13.0079 (5) Å

  • b = 9.9079 (4) Å

  • c = 17.0469 (9) Å

  • [beta] = 103.674 (4)°

  • V = 2134.75 (16) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.08 mm-1

  • T = 293 K

  • 0.3 × 0.2 × 0.2 mm

Data collection
  • Oxford Diffraction Xcalibur Sapphire3 diffractometer

  • Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010[Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]) Tmin = 0.920, Tmax = 1.000

  • 19519 measured reflections

  • 4162 independent reflections

  • 2399 reflections with I > 2[sigma](I)

  • Rint = 0.047

Refinement
  • R[F2 > 2[sigma](F2)] = 0.055

  • wR(F2) = 0.154

  • S = 1.03

  • 4162 reflections

  • 292 parameters

  • 12 restraints

  • H-atom parameters constrained

  • [Delta][rho]max = 0.21 e Å-3

  • [Delta][rho]min = -0.15 e Å-3

Data collection: CrysAlis PRO (Oxford Diffraction, 2010[Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 (Farrugia, 2012)[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]; software used to prepare material for publication: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: GK2544 ).


Acknowledgements

RK acknowledges the Department of Science & Technology for access to the single-crystal X-ray diffractometer sanctioned as a National Facility under project No. SR/S2/CMP-47/2003. BN thanks the UGC for financial assistance through the BSR one-time grant for the purchase of chemicals. PSN thanks Mangalore University for research facilities and the DST-PURSE for financial assistance.

References

Dutkiewicz, G., Shetty, D. N., Narayana, B., Yathirajan, H. S. & Kubicki, M. (2012). Acta Cryst. E68, o1324.  [CSD] [CrossRef] [details]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Hu, T.-P. (2006). Acta Cryst. E62, o2270-o2271.  [CSD] [CrossRef] [details]
Liu, S.-X., Tian, X., Zhen, X.-L., Li, Z.-C. & Han, J.-R. (2008). Acta Cryst. E64, o2245.  [CrossRef] [details]
Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.
Patole, J., Shingnapurkar, D., Padhyea, S. & Ratledge, C. (2006). Bioorg. Med. Chem. Lett. 16, 1514-1517.  [CrossRef] [PubMed] [ChemPort]
Satyanarayana, V. S. V., Sreevani, P., Sivakumar, A. & Vijayakumar, V. (2008). Arkivoc, 17, 221-233.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Shi, L., Ge, H., Tan, S., Li, H., Song, Y., Zhu, H. & Tan, R. (2007). Eur. J. Med. Chem. 42, 558-564.  [ISI] [CrossRef] [PubMed] [ChemPort]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]


Acta Cryst (2013). E69, o115  [ doi:10.1107/S1600536812050891 ]

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