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

Kant, R.; Gupta, V.K.; Kapoor, K.; Shripanavar, C.S.; Deshmukh, M.B.; Banerjee, K.

doi:10.1107/S1600536812042316

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 (C-C) = 0.004 Å
Disorder in main residue
R = 0.059
wR = 0.154
Data-to-parameter ratio = 12.7
Details

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

Rajni Kant,^a ^* Vivek K. Gupta,^a Kamini Kapoor,^a Chetan S. Shripanavar,^b Madhukar B. Deshmukh ^c and Kaushik Banerjee ^b

^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-HO hydrogen bonds link molecules into dimers that are further connected by C-HO and C-HF 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); Ammermann et al. (2000). For a related structure, see: Kant et al. (2012).

Experimental

Crystal data

C₁₇H₁₄F₃NO₄
M_r = 353.29
Triclinic, $[P \overline 1]$
a = 7.4701 (4) Å
b = 10.1619 (5) Å
c = 11.8219 (5) Å
= 94.721 (4)°
= 100.079 (4)°
= 110.685 (5)°
V = 816.42 (7) Å³
Z = 2
Mo K radiation
= 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 $[Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]$ ) T_min = 0.821, T_max = 1.000
19533 measured reflections
3214 independent reflections
1988 reflections with I > 2(I)
R_int = 0.057

Refinement

R[F² > 2(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
_max = 0.24 e Å^-3
_min = -0.40 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O4-H41O3ⁱ	0.85 (4)	1.78 (4)	2.626 (3)	174 (4)
C15-H15O3ⁱⁱ	0.93	2.58	3.392 (3)	146
C17-H17AF11Aⁱⁱⁱ	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); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: PLATON (Spek, 2009).

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.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
Kant, R., Gupta, V. K., Kapoor, K., Shripanavar, C. S. & Banerjee, K. (2012). Acta Cryst. E68, o2425.
Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.

organic compounds