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Volume 69 
Part 5 
Page o726  
May 2013  

Received 13 March 2013
Accepted 1 April 2013
Online 13 April 2013

Key indicators
Single-crystal X-ray study
T = 100 K
Mean [sigma](C-C) = 0.002 Å
R = 0.062
wR = 0.136
Data-to-parameter ratio = 22.0
Details
Open access

1-[5-(2H-1,3-Benzodioxol-5-yl)-3-(4-methylphenyl)-2-pyrazolin-1-yl]ethanone

aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and bDepartment of PG studies in Chemistry, Government Science College, Hassan 573 201, India
Correspondence e-mail: arazaki@usm.my

In the title compound, C19H18N2O3, the pyrazoline ring is close to being planar (r.m.s. deviation = 0.035 Å) and subtends dihedral angles of 2.11 (8) and 82.63 (8)° with the p-tolyl and benzene rings, respectively. In the crystal, C-H...O and C-H...N hydrogen bonds link the molecules, forming a three-dimensional network. A weak C-H...[pi] interaction involving the benzene ring is also observed.

Related literature

For background to pyrazoline derivatives, see: Mamolo et al. (2003[Mamolo, M. G., Zampieri, D., Falagiani, V., Vio, L. & Banfi, E. (2003). Il Farmaco, 58, 315-322.]); Bansal et al. (2001[Bansal, E., Srivastava, V. K. & Kumar, A. (2001). Eur. J. Med. Chem. 36, 81-92.]); Manna et al. (2005[Manna, F., Chimenti, F., Fioravanti, R., Bolasco, A., Seecci, D., Chimenti, P., Ferlini, C. & Scambia, G. (2005). Bioorg. Med. Chem. Lett. 15, 4632-4635.]); Ahn et al. (2004[Ahn, J. H., Kim, H. M., Jung, S. H., Kang, S. K., Kim, K. R., Rhee, S. D., Yang, S. D., Cheon, H. G. & Kim, S. S. (2004). Bioorg. Med. Chem. Lett. 14, 4461-4465.]); Rajendra Prasad et al. (2005[Rajendra Prasad, Y. R., Lakshamana Rao, A., Prasoona, L., Murali, K. & Ravi Kumar, P. (2005). Bioorg. Med. Lett. 15, 5030-5034.]). For a related structure, see: Du (2009[Du, C.-L. (2009). Acta Cryst. E65, o29.]). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986[Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105-107.]).

[Scheme 1]

Experimental

Crystal data
  • C19H18N2O3

  • Mr = 322.35

  • Monoclinic, P 21 /c

  • a = 7.9564 (1) Å

  • b = 24.1170 (4) Å

  • c = 8.4660 (1) Å

  • [beta] = 105.380 (1)°

  • V = 1566.32 (4) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.09 mm-1

  • T = 100 K

  • 0.35 × 0.26 × 0.18 mm

Data collection
  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.968, Tmax = 0.984

  • 18850 measured reflections

  • 4828 independent reflections

  • 3778 reflections with I > 2[sigma](I)

  • Rint = 0.032

Refinement
  • R[F2 > 2[sigma](F2)] = 0.062

  • wR(F2) = 0.136

  • S = 1.09

  • 4828 reflections

  • 219 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.39 e Å-3

  • [Delta][rho]min = -0.29 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C1-C3/C5-C7 benzene ring.

D-H...A D-H H...A D...A D-H...A
C2-H2A...O3i 0.95 2.42 3.229 (2) 142
C4-H4A...O3ii 0.99 2.38 3.225 (2) 143
C9-H9B...O2iii 0.99 2.59 3.371 (2) 136
C18-H18B...N2iv 0.98 2.56 3.526 (2) 169
C19-H19A...O3v 0.98 2.57 3.377 (2) 139
C19-H19A...Cg1vi 0.98 2.93 3.6013 (18) 127
Symmetry codes: (i) -x+1, -y+1, -z; (ii) x, y, z+1; (iii) x+1, y, z; (iv) [x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]; (v) [x+1, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]; (vi) [x+1, -y+{\script{1\over 2}}, z-{\script{1\over 2}}].

Data collection: APEX2 (Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. 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: SHELXTL; software used to prepare material for publication: SHELXTL and 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: HB7056 ).


Acknowledgements

The authors thank Universiti Sains Malaysia (USM) for the Research University Grant (1001/PFIZIK/811160). WSL also thanks Malaysian Government and USM for the award of the post of Research Officer under the Research University Grant (1001/PFIZIK/811160).

References

Ahn, J. H., Kim, H. M., Jung, S. H., Kang, S. K., Kim, K. R., Rhee, S. D., Yang, S. D., Cheon, H. G. & Kim, S. S. (2004). Bioorg. Med. Chem. Lett. 14, 4461-4465.  [CrossRef] [PubMed] [ChemPort]
Bansal, E., Srivastava, V. K. & Kumar, A. (2001). Eur. J. Med. Chem. 36, 81-92.  [ISI] [CrossRef] [PubMed] [ChemPort]
Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105-107.  [CrossRef] [ChemPort] [ISI] [details]
Du, C.-L. (2009). Acta Cryst. E65, o29.  [CSD] [CrossRef] [details]
Mamolo, M. G., Zampieri, D., Falagiani, V., Vio, L. & Banfi, E. (2003). Il Farmaco, 58, 315-322.  [CrossRef] [PubMed] [ChemPort]
Manna, F., Chimenti, F., Fioravanti, R., Bolasco, A., Seecci, D., Chimenti, P., Ferlini, C. & Scambia, G. (2005). Bioorg. Med. Chem. Lett. 15, 4632-4635.  [CrossRef] [PubMed] [ChemPort]
Rajendra Prasad, Y. R., Lakshamana Rao, A., Prasoona, L., Murali, K. & Ravi Kumar, P. (2005). Bioorg. Med. Lett. 15, 5030-5034.  [CrossRef] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [ChemPort] [details]


Acta Cryst (2013). E69, o726  [ doi:10.1107/S1600536813008817 ]

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