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

Kant, R.; Gupta, V.K.; Kapoor, K.; Nayak, P.S.; Sarojini, B.K.; Narayana, B.

doi:10.1107/S1600536812050891

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 (C-C) = 0.003 Å
Disorder in main residue
R = 0.055
wR = 0.154
Data-to-parameter ratio = 14.3
Details

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

Rajni Kant,^a ^* Vivek K. Gupta,^a Kamini Kapoor,^a Prakash S. Nayak,^b B. K. Sarojini ^c and B. Narayana ^b

^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). Acta Cryst. E68, o1324].

Related literature

For potential applications of Schiff bases, see: Patole et al. (2006); Shi et al.(2007); Satyanarayana et al. (2008). For related structures, see: Liu et al.(2008); Hu, (2006). For the other monoclinic polymorph, see Dutkiewicz et al., (2012).

Experimental

Crystal data

C₂₅H₂₃N₃O₂
M_r = 397.46
Monoclinic, P 2₁ /n
a = 13.0079 (5) Å
b = 9.9079 (4) Å
c = 17.0469 (9) Å
= 103.674 (4)°
V = 2134.75 (16) Å³
Z = 4
Mo K radiation
= 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 $[Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]$ ) T_min = 0.920, T_max = 1.000
19519 measured reflections
4162 independent reflections
2399 reflections with I > 2(I)
R_int = 0.047

Refinement

R[F² > 2(F²)] = 0.055
wR(F²) = 0.154
S = 1.03
4162 reflections
292 parameters
12 restraints
H-atom parameters constrained
_max = 0.21 e Å^-3
_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); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 2012); software used to prepare material for publication: PLATON (Spek, 2009).

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.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.
Hu, T.-P. (2006). Acta Cryst. E62, o2270-o2271.
Liu, S.-X., Tian, X., Zhen, X.-L., Li, Z.-C. & Han, J.-R. (2008). Acta Cryst. E64, o2245.
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.
Satyanarayana, V. S. V., Sreevani, P., Sivakumar, A. & Vijayakumar, V. (2008). Arkivoc, 17, 221-233.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Shi, L., Ge, H., Tan, S., Li, H., Song, Y., Zhu, H. & Tan, R. (2007). Eur. J. Med. Chem. 42, 558-564.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.