4-[(Dieth­oxy­phosphino­yl)meth­yl]benzoic acid

Karthikeyan, S.; Sethusankar, K.; Rajeshwaran, G.G.; Mohanakrishnan, A.K.

doi:10.1107/S1600536811008282

Volume 67
Part 4
Page o831
April 2011

Received 1 March 2011
Accepted 4 March 2011
Online 9 March 2011

Key indicators
Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.002 Å
R = 0.035
wR = 0.106
Data-to-parameter ratio = 17.9
Details

4-[(Diethoxyphosphinoyl)methyl]benzoic acid

S. Karthikeyan,^a K. Sethusankar,^a ^* Ganesan Gobi Rajeshwaran ^b and Arasambattu K. Mohanakrishnan ^b

^aDepartment of Physics, RKM Vivekananda College (Autonomous), Chennai 600 004, India, and ^bDepartment of Organic Chemistry, University of Madras, Maraimalai Campus, Chennai 600 025, India
Correspondence e-mail: ksethusankar@yahoo.co.in

In the title compound, C₁₂H₁₇N₂O₅P, the phosphonate group is almost orthogonal to both the ethyl groups, with a dihedral angle of 83.75 (11)°. In the crystal, molecules are linked into centrosymmetric dimers via pairs of O-HO hydrogen bonds with an R₂²(20) graph-set motif. The crystal structure is further consolidated by weak C-H [pi] interactions.

Related literature

For applications of phosphonate derivatives, see: Hirschmann et al. (1994). For related structures, see: An et al. (2008); Chen et al. (2008). For graph-set motifs, see: Bernstein et al. (1995).

Experimental

Crystal data

C₁₂H₁₇O₅P
M_r = 272.23
Monoclinic, P 2₁ /n
a = 9.6505 (5) Å
b = 12.1706 (6) Å
c = 11.8156 (6) Å
= 108.926 (2)°
V = 1312.74 (12) Å³
Z = 4
Mo K radiation
= 0.22 mm^-1
T = 293 K
0.23 × 0.20 × 0.20 mm

Data collection

Bruker SMART APEXII area-detector diffractometer
13181 measured reflections
2960 independent reflections
2441 reflections with I > 2(I)
R_int = 0.025

Refinement

R[F² > 2(F²)] = 0.035
wR(F²) = 0.106
S = 1.04
2960 reflections
165 parameters
H-atom parameters constrained
_max = 0.31 e Å^-3
_min = -0.22 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C2-C7 benzene ring.

D-HA	D-H	HA	DA	D-HA
O4-H4AO1ⁱ	0.82	1.87	2.644 (2)	158
C12-H12CCg1ⁱⁱ	0.96	2.97	3.853 (2)	153
Symmetry codes: (i) -x+1, -y, -z+2; (ii) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT; 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: SHELXL97, PARST (Nardelli, 1983) and PLATON (Spek, 2009).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: PV2396 ).

Acknowledgements

SK and KS thank Dr Babu Varghese, SAIF, IIT, Chennai, India, for the data collection.

References

An, L.-T., Gong, G.-X., Liu, X., Xia, M. & Zhou, J.-F. (2008). Acta Cryst. E64, o1320.
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.
Bruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Chen, C., Jin, W. & Li, X. (2008). Acta Cryst. E64, o144.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
Hirschmann, R., Smith, A. B., Taylor, C. M., Benkovic, P. A., Taylor, S., Yager, K. M., Sprengler, P. A. & Benkovic, S. J. (1994). Science, 265, 234-237.
Nardelli, M. (1983). Acta Cryst. C39, 1141-1142.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.

organic compounds