N-(3,5-Dimethyl­phen­yl)succinamic acid

Saraswathi, B.S.; Foro, S.; Gowda, B.T.

doi:10.1107/S1600536810053055

Volume 67
Part 1
Page o234
January 2011

Received 16 December 2010
Accepted 17 December 2010
Online 24 December 2010

Key indicators
Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.004 Å
R = 0.054
wR = 0.147
Data-to-parameter ratio = 15.8
Details

N-(3,5-Dimethylphenyl)succinamic acid

B. S. Saraswathi,^a Sabine Foro ^b and B. Thimme Gowda ^a ^*

^aDepartment of Chemistry, Mangalore University, Mangalagangotri 574 199, Mangalore, India, and ^bInstitute of Materials Science, Darmstadt University of Technology, Petersenstrasse 23, D-64287 Darmstadt, Germany
Correspondence e-mail: gowdabt@yahoo.com

In the title compound, C₁₂H₁₅NO₃, the N-H and C=O bonds are anti to each other. The C=O and O-H bonds of the acid group display an antiperiplanar orientation relative to each other. The crystal packing features a three-dimensional network of molecules held together by O-HO and N-HO hydrogen bonds.

Related literature

For our study of the effect of ring and side-chain substitutions on the crystal structures of anilides, see: Gowda et al. (2009 2010a,b). For modes of interlinking carboxylic acids by hydrogen bonds, see: Leiserowitz (1976). The packing of molecules involving dimeric hydrogen-bonded association of each carboxyl group with a centrosymmetrically related neighbor has also been observed, see: Jagannathan et al. (1994).

Experimental

Crystal data

C₁₂H₁₅NO₃
M_r = 221.25
Monoclinic, P 2₁ /n
a = 14.346 (2) Å
b = 5.0225 (9) Å
c = 17.860 (3) Å
= 112.00 (2)°
V = 1193.2 (3) Å³
Z = 4
Mo K radiation
= 0.09 mm^-1
T = 293 K
0.45 × 0.08 × 0.05 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ) T_min = 0.961, T_max = 0.996
4452 measured reflections
2419 independent reflections
1593 reflections with I > 2(I)
R_int = 0.019

Refinement

R[F² > 2(F²)] = 0.054
wR(F²) = 0.147
S = 1.03
2419 reflections
153 parameters
H atoms treated by a mixture of independent and constrained refinement
_max = 0.20 e Å^-3
_min = -0.18 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1-H1NO2ⁱ	0.88 (2)	2.01 (2)	2.881 (2)	171 (2)
O3-H3OO1ⁱⁱ	0.86 (3)	1.77 (3)	2.630 (2)	172 (3)
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: CrysAlis CCD (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ); cell refinement: CrysAlis RED (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BT5440 ).

Acknowledgements

BSS thanks the University Grants Commission, Government of India, New Delhi, for the award of a research fellowship under its faculty improvement program.

References

Gowda, B. T., Foro, S., Saraswathi, B. S. & Fuess, H. (2010a). Acta Cryst. E66, o394.
Gowda, B. T., Foro, S., Saraswathi, B. S. & Fuess, H. (2010b). Acta Cryst. E66, o436.
Gowda, B. T., Foro, S., Saraswathi, B. S., Terao, H. & Fuess, H. (2009). Acta Cryst. E65, o466.
Jagannathan, N. R., Rajan, S. S. & Subramanian, E. (1994). J. Chem. Crystallogr. 24, 75-78.
Leiserowitz, L. (1976). Acta Cryst. B32, 775-802.
Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. 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