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Volume 69 
Part 6 
Page o840  
June 2013  

Received 24 February 2013
Accepted 30 April 2013
Online 4 May 2013

Key indicators
Single-crystal X-ray study
T = 273 K
Mean [sigma](C-C) = 0.005 Å
R = 0.070
wR = 0.246
Data-to-parameter ratio = 12.8
Details
Open access

1-[3-(2-Benzyloxy-6-hydroxy-4-methylphenyl)-5-[3,5-bis(trifluoromethyl)phenyl]-4,5-dihydro-1H-pyrazol-1-yl]propane-1-one

aDepartment of Physics, Sardar Patel University, Vallabh Vidyanagar, Gujarat 388 120, India, and bP. G. Center in Chemistry, Smt. S. M. Panchal Science College, Talod, Gujarat 383 215, India
Correspondence e-mail: u_h_patel@yahoo.com

In the title compound, C28H24F6N2O3, the mean plane of the central pyrazoline ring forms dihedral angles of 2.08 (9) and 69.02 (16)° with the 2-benzyloxy-6-hydroxy-4-methylphenyl and 3,5-bis(trifluoromethyl)phenyl rings, respectively. The dihedral angle between the mean planes of the pyrazoline and 3,5-bis(trifluoromethyl)phenyl rings is 68.97 (9)°. An intramolecular O-H...N hydrogen bond is observed, which forms an S(6) graph-set motif. In the crystal, pairs of weak C-H...F halogen interactions link the molecules into inversion dimers while molecular chains along [100] are formed by C-H...O contacts.

Related literature

For pharmacalogical and anticancer properties of pyrazoline derivatives, see: Smith et al. (2001[Smith, S. R., Denhardt, G. & Terminelli, C. (2001). Eur. J. Pharmacol. 432, 107-109.]). For graph-set motifs, see: Bernstein et al., (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]). For related structures, see: Patel et al. (2007[Patel, U. H., Patel, P. D. & Thakker, N. (2007). Acta Cryst. C63, o337-o339.], 2012[Patel, U. H., Gandhi, S. A., Barot, V. M. & Patel, M. C. (2012). Acta Cryst. E68, o2926-o2927.]).

[Scheme 1]

Experimental

Crystal data
  • C28H24F6N2O3

  • Mr = 550.49

  • Monoclinic, P 21 /n

  • a = 4.8822 (2) Å

  • b = 23.4752 (9) Å

  • c = 22.4311 (9) Å

  • [beta] = 91.494 (2)°

  • V = 2569.97 (18) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.12 mm-1

  • T = 273 K

  • 0.54 × 0.34 × 0.10 mm

Data collection
  • Bruker Kappa APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2008[Bruker (2008). SADABS, SAINT and APEX2. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.951, Tmax = 0.988

  • 19610 measured reflections

  • 4514 independent reflections

  • 2491 reflections with I > 2[sigma](I)

  • Rint = 0.075

Refinement
  • R[F2 > 2[sigma](F2)] = 0.070

  • wR(F2) = 0.246

  • S = 1.00

  • 4514 reflections

  • 352 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.56 e Å-3

  • [Delta][rho]min = -0.41 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O16-H16...N2 0.82 1.84 2.568 (3) 147
C31-H31...O9i 0.93 2.67 3.490 (4) 148
C21-H21...F37ii 0.93 2.72 3.488 (6) 140
C29-H29...F33iii 0.93 2.64 3.490 (5) 152
Symmetry codes: (i) x+1, y, z; (ii) [-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]; (iii) -x, -y+1, -z+2.

Data collection: APEX2 (Bruker, 2008[Bruker (2008). SADABS, SAINT and APEX2. Bruker AXS Inc., Madison, Wisconsin, USA.] ); cell refinement: SAINT (Bruker, 2008[Bruker (2008). SADABS, SAINT and APEX2. 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: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); 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: JJ2162 ).


Acknowledgements

We are thankful to the DST (New Delhi) FIST facility for providing the single-crystal diffractometer at the Department of Physics, Sardar Patel University, Vallabh Vidyanagar, Gujarat. SG is also thankful to UGC, New Delhi, for the financial support (RFSMS) to carry out this research.

References

Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.  [CrossRef] [ChemPort] [ISI]
Bruker (2008). SADABS, SAINT and APEX2. Bruker AXS Inc., Madison, Wisconsin, USA.
Patel, U. H., Gandhi, S. A., Barot, V. M. & Patel, M. C. (2012). Acta Cryst. E68, o2926-o2927.  [CSD] [CrossRef] [ChemPort] [details]
Patel, U. H., Patel, P. D. & Thakker, N. (2007). Acta Cryst. C63, o337-o339.  [CSD] [CrossRef] [ChemPort] [details]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]
Smith, S. R., Denhardt, G. & Terminelli, C. (2001). Eur. J. Pharmacol. 432, 107-109.  [ISI] [CrossRef] [PubMed] [ChemPort]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [ChemPort] [details]
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [ISI] [CrossRef] [ChemPort] [details]


Acta Cryst (2013). E69, o840  [ doi:10.1107/S160053681301180X ]

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