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Volume 69 
Part 10 
Page o1528  
October 2013  

Received 2 September 2013
Accepted 4 September 2013
Online 12 September 2013

Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.005 Å
R = 0.084
wR = 0.242
Data-to-parameter ratio = 11.6
Details
Open access

1-{3-(4-Methylphenyl)-5-[5-(2-nitrophenyl)furan-2-yl]-4,5-dihydro-1H-pyrazol-1-yl}ethanone

aDepartment of Studies in Physics, University of Mysore, Manasagangotri, Mysore 570 006, India, and bDepartment of Studies in Chemistry, Mangalore University, Mangalagangotri, Mangalore 574 199, India
Correspondence e-mail: dr@physics.uni-mysore.ac.in

In the title compound, C22H19N3O4, the dihedral angle between the furan and pyrazole rings is 82.73 (19)° while the dihedral angles between the furan and pyrazole rings and their attached benzene rings are 31.93 (18) and 1.88 (18)°, respectively. In the crystal, inversion dimers linked by pairs of C-H...O hydrogen bonds generate R22(16) loops. In addition, weak C-H...[pi] and aromatic [pi]-[pi] stacking [minimum centroid-centroid distance = 3.5374 (17) Å] interactions are observed.

Related literature

For background to the biological properties of pyrazole derivatives, see: Amir et al. (2008[Amir, M., Kumar, H. & Khan, S. A. (2008). Bioorg. Med. Chem. Lett. 18, 918-922.]); Husain et al. (2008[Husain, K., Abid, M. & Azam, A. (2008). Eur. J. Med. Chem. 43, 393-403.]).

[Scheme 1]

Experimental

Crystal data
  • C22H19N3O4

  • Mr = 389.40

  • Triclinic, [P \overline 1]

  • a = 7.6235 (3) Å

  • b = 10.5652 (4) Å

  • c = 13.1177 (4) Å

  • [alpha] = 103.344 (2)°

  • [beta] = 95.025 (2)°

  • [gamma] = 108.221 (2)°

  • V = 961.78 (6) Å3

  • Z = 2

  • Cu K[alpha] radiation

  • [mu] = 0.78 mm-1

  • T = 296 K

  • 0.23 × 0.22 × 0.21 mm

Data collection
  • Bruker X8 Proteum CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2013[Bruker (2013). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.842, Tmax = 0.854

  • 10640 measured reflections

  • 3083 independent reflections

  • 2186 reflections with I > 2[sigma](I)

  • Rint = 0.138

Refinement
  • R[F2 > 2[sigma](F2)] = 0.084

  • wR(F2) = 0.242

  • S = 1.06

  • 3083 reflections

  • 265 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.40 e Å-3

  • [Delta][rho]min = -0.38 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg4 is the centroid of the C23-C28 ring.

D-H...A D-H H...A D...A D-H...A
C14-H14...O19i 0.93 2.56 3.462 (4) 162
C18-H18C...Cg4ii 0.96 2.69 3.595 (4) 158
Symmetry codes: (i) -x, -y, -z+2; (ii) -x, -y, -z+1.

Data collection: APEX2 (Bruker, 2013[Bruker (2013). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2013[Bruker (2013). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; 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: Mercury (Macrae et al., 2008[Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.]); software used to prepare material for publication: SHELXL97.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB7133 ).


Acknowledgements

The authors thank the IOE, University of Mysore, for providing the single-crystal X-ray diffraction facility. VN is grateful to the UGC, New Delhi, for the award of an RFSMS Fellowship. RD acknowledges the UGC, New Delhi, for financial support under the Major Research Project Scheme [UGC MRP No. F.41-882/2012 (SR) dated 01/07/2012].

References

Amir, M., Kumar, H. & Khan, S. A. (2008). Bioorg. Med. Chem. Lett. 18, 918-922.  [CrossRef] [PubMed] [ChemPort]
Bruker (2013). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Husain, K., Abid, M. & Azam, A. (2008). Eur. J. Med. Chem. 43, 393-403.  [Web of Science] [CrossRef] [PubMed] [ChemPort]
Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]


Acta Cryst (2013). E69, o1528  [ doi:10.1107/S1600536813024690 ]

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