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Volume 67 
Part 10 
Page o2550  
October 2011  

Received 26 August 2011
Accepted 27 August 2011
Online 3 September 2011

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Key indicators
Single-crystal X-ray study
T = 100 K
Mean [sigma](C-C) = 0.005 Å
R = 0.060
wR = 0.140
Data-to-parameter ratio = 16.9
Details
Open access

(E)-1-(Naphthalen-1-yl)-3-(1-phenyl-1H-pyrazol-4-yl)prop-2-en-1-one

Abdullah M. Asiri,a,b Abdulrahman O. Al-Youbi,a Hassan M. Faidallah,a Khalid A. Alamrya and Seik Weng Ngc,a*

aChemistry Department, Faculty of Science, King Abdulaziz University, PO Box 80203 Jeddah, Saudi Arabia,bCenter of Excellence for Advanced Materials Research, King Abdulaziz University, PO Box 80203 Jeddah, Saudi Arabia, and cDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
Correspondence e-mail: seikweng@um.edu.my

In the title molecule, C22H16N2O, the phenyl ring is twisted slightly with respect to the plane of the central pyrazole ring [dihedral angle = 14.8 (2)°]; the central ring is connected to the naphthyl ring through a -CH=CH-C(=O)- fragment, whose C=C double bond has an E configuration. The pyrazole ring and naphthalene ring system are twisted by 46.3 (1)°. Weak intermolecular C-H...O hydrogen bonds link the molecules, forming supramolecular chains running along the a axis. The crystal studied was a non-merohedral twin with a component ratio of 0.544 (2):0.456 (2).

Related literature

For related structures; see: Diánez & López-Castro (1990[Diánez, M. J. & López-Castro, A. (1990). Acta Cryst. C46, 1718-1720.]); Jones et al. (1984[Jones, R. A., Gonzalez, B. A., Arques, J. S., Pardo, J. Q. & King, T. J. (1984). J. Chem. Soc. Perkin Trans. 1, pp. 1423-1425.]). For the synthesis, see: Finar (1961[Finar, I. L. (1961). J. Chem. Soc. pp. 674-679.]); Finar & Lord (1959[Finar, I. L. & Lord, G. H. (1959). J. Chem. Soc. pp. 1819-1823.]); Jones et al. (1984[Jones, R. A., Gonzalez, B. A., Arques, J. S., Pardo, J. Q. & King, T. J. (1984). J. Chem. Soc. Perkin Trans. 1, pp. 1423-1425.]).

[Scheme 1]

Experimental

Crystal data

  • C22H16N2O

  • Mr = 324.37

  • Monoclinic, P 21 /n

  • a = 5.8457 (6) Å

  • b = 10.322 (2) Å

  • c = 26.626 (2) Å

  • [beta] = 92.322 (9)°

  • V = 1605.3 (4) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.08 mm-1

  • T = 100 K

  • 0.25 × 0.10 × 0.10 mm
Data collection

  • Agilent SuperNova Dual diffractometer with an Atlas detector

  • Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010[Agilent (2010). CrysAlis PRO. Agilent Technologies, Yarnton, England.]) Tmin = 0.980, Tmax = 0.992

  • 3824 measured reflections

  • 3825 independent reflections

  • 2494 reflections with I > 2[sigma](I)

  • Rint = 0.105
Refinement

  • R[F2 > 2[sigma](F2)] = 0.060

  • wR(F2) = 0.140

  • S = 0.96

  • 3825 reflections

  • 227 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.31 e Å-3

  • [Delta][rho]min = -0.34 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C9-H9...O1i 0.95 2.46 3.397 (4) 167
Symmetry code: (i) x-1, y, z.

Data collection: CrysAlis PRO (Agilent, 2010[Agilent (2010). CrysAlis PRO. Agilent Technologies, 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: X-SEED (Barbour, 2001[Barbour, L. J. (2001). J. Supramol. Chem. 1, 189-191.]); software used to prepare material for publication: publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: XU5313 ).

Acknowledgements

We thank King Abdulaziz University and the University of Malaya for supporting this study.

References

Agilent (2010). CrysAlis PRO. Agilent Technologies, Yarnton, England.
Barbour, L. J. (2001). J. Supramol. Chem. 1, 189-191.  [CrossRef] [ChemPort]
Diánez, M. J. & López-Castro, A. (1990). Acta Cryst. C46, 1718-1720.  [CrossRef] [details]
Finar, I. L. (1961). J. Chem. Soc. pp. 674-679.  [CrossRef]
Finar, I. L. & Lord, G. H. (1959). J. Chem. Soc. pp. 1819-1823.  [CrossRef]
Jones, R. A., Gonzalez, B. A., Arques, J. S., Pardo, J. Q. & King, T. J. (1984). J. Chem. Soc. Perkin Trans. 1, pp. 1423-1425.  [CrossRef]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [ISI] [CrossRef] [ChemPort] [details]

Acta Cryst (2011). E67, o2550  [ doi:10.1107/S1600536811035124 ]

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