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Volume 69 
Part 4 
Pages o594-o595  
April 2013  

Received 15 March 2013
Accepted 20 March 2013
Online 28 March 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.002 Å
R = 0.040
wR = 0.107
Data-to-parameter ratio = 13.1
Details
Open access

(E)-3-(4-Methoxyphenyl)-3-[3-(4-methoxyphenyl)-1H-pyrazol-1-yl]prop-2-enal

aDepartment of Lighthouses & Lightships, Ministry of Shipping, Nagapattinam Lighthouse & DGPS Station, Nagapattinam 611 001, India,bDepartment of Physics, University College of Engineering, Nagercoil, Anna University, Tirunelveli Region, Nagercoil 629 004, India,cDepartment of Physics, Kalasalingam University, Anand Nagar, Krishnan Koil 626 190, India,dInstitute of Organic Chemistry and Technology, Faculty of Chemical Technology, University of Pardubice, Pardubice 53210, Czech Republic, and eDepartment of Organic Chemistry, Madurai Kamaraj University, Madurai 625 021, India
Correspondence e-mail: athi81s@yahoo.co.in

In the title molecule, C20H18N2O3, the pyrazole ring forms a dihedral angle of 2.2 (1)° with its methoxyphenyl substituent and a dihedral angle of 67.2 (1)° with the benzene substituent on the propenal unit. In the crystal, molecules are connected by weak C-H...O hydrogen bonds, forming R22(26) and R22(28) cyclic dimers that lie about crystallographic inversion centres. These dimers are further linked through C-H...O and C-H...N hydrogen bonds, forming C(8), C(9), C(10) and C(16) chain motifs. These primary motifs are further linked to form secondary C22(15) chains and R22(18) rings.

Related literature

For the pharmacological and medicinal properties of pyrazole compounds, see: Baraldi et al. (1998[Baraldi, P. G., Manfredini, S., Romagnoli, R., Stevanato, L., Zaid, A. N. & Manservigi, R. (1998). Nucleosides Nucleotides, 17, 2165-2171.]); Bruno et al. (1990[Bruno, O., Bondavalli, F., Ranise, A., Schenone, P., Losasso, C., Cilenti, L., Matera, C. & Marmo, E. (1990). Il Farmaco, 45, 147-66.]); Chen & Li (1998[Chen, H. S. & Li, Z. M. (1998). Chem. J. Chin. Univ. 19, 572-576.]); Cottineau et al. (2002[Cottineau, B., Toto, P., Marot, C., Pipaud, A. & Chenault, J. (2002). Bioorg. Med. Chem. 12, 2105-2108.]); Londershausen (1996[Londershausen, M. (1996). Pestic. Sci. 48, 269-274.]); Mishra et al. (1998[Mishra, P. D., Wahidullah, S. & Kamat, S. Y. (1998). Indian J. Chem. Sect. B, 37, 199-200.]); Smith et al. (2001[Smith, S. R., Denhardt, G. & Terminelli, C. (2001). Eur. J. Pharmacol. 432, 107-119.]). For related structures, see: Susindran et al. (2010a[Susindran, V., Athimoolam, S., Bahadur, S. A., Manikannan, R. & Muthusubramanian, S. (2010a). Acta Cryst. E66, o2594-o2595.],b[Susindran, V., Athimoolam, S., Bahadur, S. A., Sridhar, B., Manikannan, R. & Muthusubramanian, S. (2010b). Acta Cryst. E66, o577.], 2012[Susindran, V., Athimoolam, S., Bahadur, S. A., Manikannan, R. & Muthusubramanian, S. (2012). Acta Cryst. E68, o2845.]). For hydrogen-bond motifs, see: Etter et al. (1990[Etter, M. C., MacDonald, J. C. & Bernstein, J. (1990). Acta Cryst. B46, 256-262.]).

[Scheme 1]

Experimental

Crystal data
  • C20H18N2O3

  • Mr = 334.36

  • Triclinic, [P \overline 1]

  • a = 8.8081 (6) Å

  • b = 9.8474 (5) Å

  • c = 10.3292 (8) Å

  • [alpha] = 94.997 (12)°

  • [beta] = 93.811 (14)°

  • [gamma] = 106.719 (13)°

  • V = 850.85 (10) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.09 mm-1

  • T = 293 K

  • 0.22 × 0.19 × 0.15 mm

Data collection
  • Bruker SMART APEX CCD diffractometer

  • 8253 measured reflections

  • 2993 independent reflections

  • 2677 reflections with I > 2[sigma](I)

  • Rint = 0.020

Refinement
  • R[F2 > 2[sigma](F2)] = 0.040

  • wR(F2) = 0.107

  • S = 1.04

  • 2993 reflections

  • 228 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.14 e Å-3

  • [Delta][rho]min = -0.25 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C5-H5...O3i 0.93 2.73 3.366 (2) 126
C18-H18C...N2i 0.96 2.74 3.627 (2) 155
C14-H14...O2ii 0.93 2.49 3.301 (2) 145
C33-H33...O1iii 0.93 2.82 3.642 (2) 148
C37-H37B...O2iv 0.96 2.75 3.688 (2) 166
C37-H37C...O1v 0.96 2.76 3.650 (2) 155
Symmetry codes: (i) x, y-1, z; (ii) x+1, y, z; (iii) -x+2, -y+1, -z+1; (iv) -x+1, -y+2, -z+1; (v) x, y+1, z-1.

Data collection: SMART (Bruker, 2001[Bruker (2001). SAINT and SMART. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2001[Bruker (2001). SAINT and SMART. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL; molecular graphics: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: SHELXTL.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SJ5307 ).


Acknowledgements

VS and SAB sincerely thank the Vice Chancellor and Management of Kalasalingam University, Anand Nagar, Krishnan Koil, for their support and encouragement.

References

Baraldi, P. G., Manfredini, S., Romagnoli, R., Stevanato, L., Zaid, A. N. & Manservigi, R. (1998). Nucleosides Nucleotides, 17, 2165-2171.  [CrossRef] [ChemPort]
Bruker (2001). SAINT and SMART. Bruker AXS Inc., Madison, Wisconsin, USA.
Bruno, O., Bondavalli, F., Ranise, A., Schenone, P., Losasso, C., Cilenti, L., Matera, C. & Marmo, E. (1990). Il Farmaco, 45, 147-66.  [ChemPort] [PubMed]
Chen, H. S. & Li, Z. M. (1998). Chem. J. Chin. Univ. 19, 572-576.  [ChemPort]
Cottineau, B., Toto, P., Marot, C., Pipaud, A. & Chenault, J. (2002). Bioorg. Med. Chem. 12, 2105-2108.  [ChemPort]
Etter, M. C., MacDonald, J. C. & Bernstein, J. (1990). Acta Cryst. B46, 256-262.  [CrossRef] [ISI] [details]
Londershausen, M. (1996). Pestic. Sci. 48, 269-274.  [CrossRef] [ChemPort]
Mishra, P. D., Wahidullah, S. & Kamat, S. Y. (1998). Indian J. Chem. Sect. B, 37, 199-200.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Smith, S. R., Denhardt, G. & Terminelli, C. (2001). Eur. J. Pharmacol. 432, 107-119.  [ISI] [CrossRef] [PubMed] [ChemPort]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]
Susindran, V., Athimoolam, S., Bahadur, S. A., Manikannan, R. & Muthusubramanian, S. (2010a). Acta Cryst. E66, o2594-o2595.  [CrossRef] [ChemPort] [details]
Susindran, V., Athimoolam, S., Bahadur, S. A., Sridhar, B., Manikannan, R. & Muthusubramanian, S. (2010b). Acta Cryst. E66, o577.  [CrossRef] [details]
Susindran, V., Athimoolam, S., Bahadur, S. A., Manikannan, R. & Muthusubramanian, S. (2012). Acta Cryst. E68, o2845.  [CrossRef] [details]


Acta Cryst (2013). E69, o594-o595   [ doi:10.1107/S1600536813007678 ]

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