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Volume 68 
Part 11 
Page o3163  
November 2012  

Received 24 September 2012
Accepted 9 October 2012
Online 20 October 2012

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.004 Å
Disorder in main residue
R = 0.059
wR = 0.154
Data-to-parameter ratio = 12.7
Details
Open access

3-Methoxy-2-[2-({[6-(trifluoromethyl)pyridin-2-yl]oxy}methyl)phenyl]prop-2-enoic acid

aX-ray Crystallography Laboratory, Post-Graduate Department of Physics & Electronics, University of Jammu, Jammu Tawi 180 006, India,bNational Research Centre for Grapes, Pune 412307, India, and cDepartment of Chemistry, Shivaji University, Kolhapur, 416 004, India
Correspondence e-mail: rkvk.paper11@gmail.com

The title molecule, C17H14F3NO4, consists of two nearly planar fragments, viz. the 2-benzyloxypyridine (r.m.s. deviation 0.016 Å) and (E)-3-methoxyprop2-enoic (r.m.s. deviation 0.004 Å) units, which form a dihedral angle of 84.19 (7)°. In the crystal, pairs of O-H...O hydrogen bonds link molecules into dimers that are further connected by C-H...O and C-H...F interactions into (001) layers. In addition, [pi]-[pi] stacking interactions are observed within a layer between the pyridine and benzene rings [centroid-centroid distance = 3.768 (2) Å]. The F atoms of the trifluoromethyl group are disordered over two sets of sites in a 0.53 (4):0.47 (4) ratio.

Related literature

The title compound is the acid metabolite of picoxystrobin [systematic name: methyl (E)-3-methoxy-2-{2-[6-(trifluoromethyl)-2-pyridyloxymethyl]phenyl}acrylate], a systemic fungicide with broad-spectrum bio-efficacy against various diseases of agricultural crops, see: Balba (2007[Balba, H. (2007). J. Environ. Sci. Health Part B, 42, 441-451.]); Ammermann et al. (2000[Ammermann, E., Lorenz, G., Schelberger, K., Mueller, B., Kirstgen, R. & Sauter, H. (2000). Proceedings of the BCPC Conference -Pest and Diseases, 2, 541-548.]). For a related structure, see: Kant et al. (2012[Kant, R., Gupta, V. K., Kapoor, K., Shripanavar, C. S. & Banerjee, K. (2012). Acta Cryst. E68, o2425.]).

[Scheme 1]

Experimental

Crystal data
  • C17H14F3NO4

  • Mr = 353.29

  • Triclinic, [P \overline 1]

  • a = 7.4701 (4) Å

  • b = 10.1619 (5) Å

  • c = 11.8219 (5) Å

  • [alpha] = 94.721 (4)°

  • [beta] = 100.079 (4)°

  • [gamma] = 110.685 (5)°

  • V = 816.42 (7) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.13 mm-1

  • T = 293 K

  • 0.3 × 0.2 × 0.2 mm

Data collection
  • Oxford Diffraction Xcalibur Sapphire3 diffractometer

  • Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010[Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]) Tmin = 0.821, Tmax = 1.000

  • 19533 measured reflections

  • 3214 independent reflections

  • 1988 reflections with I > 2[sigma](I)

  • Rint = 0.057

Refinement
  • R[F2 > 2[sigma](F2)] = 0.059

  • wR(F2) = 0.154

  • S = 1.04

  • 3214 reflections

  • 253 parameters

  • 6 restraints

  • H atoms treated by a mixture of independent and constrained refinement

  • [Delta][rho]max = 0.24 e Å-3

  • [Delta][rho]min = -0.40 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O4-H41...O3i 0.85 (4) 1.78 (4) 2.626 (3) 174 (4)
C15-H15...O3ii 0.93 2.58 3.392 (3) 146
C17-H17A...F11Aiii 0.96 2.41 3.135 (14) 132
Symmetry codes: (i) -x, -y+2, -z; (ii) -x, -y+1, -z; (iii) -x+1, -y+2, -z.

Data collection: CrysAlis PRO (Oxford Diffraction, 2010[Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, 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: ORTEP-3 (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]); software used to prepare material for publication: 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: GK2523 ).


Acknowledgements

RK acknowledges the Department of Science & Technology for access to the single-crystal X-ray diffractometer sanctioned as a National Facility under project No. SR/S2/CMP-47/2003.

References

Ammermann, E., Lorenz, G., Schelberger, K., Mueller, B., Kirstgen, R. & Sauter, H. (2000). Proceedings of the BCPC Conference -Pest and Diseases, 2, 541-548.
Balba, H. (2007). J. Environ. Sci. Health Part B, 42, 441-451.  [CrossRef] [ChemPort]
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  [CrossRef] [details]
Kant, R., Gupta, V. K., Kapoor, K., Shripanavar, C. S. & Banerjee, K. (2012). Acta Cryst. E68, o2425.  [CSD] [CrossRef] [details]
Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]


Acta Cryst (2012). E68, o3163  [ doi:10.1107/S1600536812042316 ]

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