N-Phenyl­succinamic acid

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

doi:10.1107/S160053681005364X

Volume 67
Part 2
Page o249
February 2011

Received 20 December 2010
Accepted 21 December 2010
Online 8 January 2011

Key indicators
Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.004 Å
R = 0.053
wR = 0.135
Data-to-parameter ratio = 13.5
Details

N-Phenylsuccinamic acid

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

^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 crystal structure of the title compound, C₁₀H₁₁NO₃, the conformations of N-H and C=O bonds in the amide segment are anti to each other. Further, the conformations of the amide O atom and the carbonyl O atom of the acid segment are anti to each other and to the adjacent -CH₂ groups. The C=O and O-H bonds of the acid group are in syn positions with respect to each other. In the crystal, the molecules are packed into infinite chains along the a axis through intermolecular N-HO and O-HO hydrogen bonds.

Related literature

For our studies of the effect of substituents on the structures of anilides, see: Gowda et al. (2009, 2010a,b). For modes of interlinking carboxylic acids by hydrogen bonds, see: Leiserowitz (1976). For the packing of molecules involving dimeric hydrogen-bonded association of each carboxyl group with a centrosymmetrically related neighbor, see: Jagannathan et al. (1994).

Experimental

Crystal data

C₁₀H₁₁NO₃
M_r = 193.20
Monoclinic, P 2₁ /c
a = 4.986 (1) Å
b = 25.108 (4) Å
c = 7.895 (2) Å
= 103.18 (2)°
V = 962.3 (3) Å³
Z = 4
Mo K radiation
= 0.10 mm^-1
T = 293 K
0.44 × 0.14 × 0.14 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 = 0.958, T_max = 0.986
3269 measured reflections
1791 independent reflections
1033 reflections with I > 2(I)
R_int = 0.022

Refinement

R[F² > 2(F²)] = 0.053
wR(F²) = 0.135
S = 0.99
1791 reflections
133 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
_max = 0.15 e Å^-3
_min = -0.13 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1-H1NO1ⁱ	0.85 (2)	2.22 (2)	3.041 (3)	161 (2)
O3-H3OO2ⁱⁱ	0.88 (2)	1.80 (2)	2.671 (2)	177 (3)
Symmetry codes: (i) x+1, y, z; (ii) -x+1, -y, -z+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: BQ2265 ).

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, o842.
Gowda, B. T., Foro, S., Saraswathi, B. S. & Fuess, H. (2010b). Acta Cryst. E66, o908.
Gowda, B. T., Foro, S., Saraswathi, B. S., Terao, H. & Fuess, H. (2009). Acta Cryst. E65, o399.
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