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Volume 69 
Part 10 
Page o1520  
October 2013  

Received 19 July 2013
Accepted 2 September 2013
Online 7 September 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.005 Å
R = 0.057
wR = 0.167
Data-to-parameter ratio = 13.5
Details
Open access

2-(Benzylcarbamoyl)nicotinic acid

aCollege of Pharmacy, Nanjing University of Chinese Medicine, Nanjing 210023, People's Republic of China,bDepartment of Applied Chemistry, Nanjing College of Chemical Technology, Nanjing 210048, People's Republic of China,cMolecular Biology Laboratory of SATCM, First Medicine College, Nanjing University of Chinese Medicine, Nanjing 210023, People's Republic of China, and dScience and Technology Department, Nanjing University of Chinese Medicine, Nanjing 210023, People's Republic of China
Correspondence e-mail: wuhaomrs@163.com

In the title compound, C14H12N2O3, the pyridine ring is twisted with respect to the phenyl ring and the carboxylic acid group at angles of 37.1 (5) and 8.1 (3)°, respectively; the phenyl ring forms a dihedral angle of 41.4 (1)° with the mean plane of the C-NH-C=O fragment. An intramolecular O-H...O hydrogen bond occurs between the carboxylic acid and carbonyl groups. In the crystal, N-H...O hydrogen bonds link molecules into a supramolecular chain running along the a-axis direction.

Related literature

For background to the title compound, see: Konshin et al. (2010[Konshin, M. E., Syropyatov, B. Y., Vakhrin, M. I., Neifel'd, P. G., Feshin, V. P., Shurov, S. N. & Odegova1, T. F. (2010). Pharm. Chem. J. 44, 476-479.]). For a related structure, see: Koch et al. (2008[Koch, C., Görls, H. & Westerhausen, M. (2008). Acta Cryst. E64, o2358.]).

[Scheme 1]

Experimental

Crystal data
  • C14H12N2O3

  • Mr = 256.26

  • Orthorhombic, P b c a

  • a = 13.024 (3) Å

  • b = 8.4110 (17) Å

  • c = 23.143 (5) Å

  • V = 2535.2 (9) Å3

  • Z = 8

  • Mo K[alpha] radiation

  • [mu] = 0.10 mm-1

  • T = 293 K

  • 0.30 × 0.20 × 0.10 mm

Data collection
  • Enraf-Nonius CAD-4 diffractometer

  • 4586 measured reflections

  • 2326 independent reflections

  • 1242 reflections with I > 2[sigma](I)

  • Rint = 0.096

  • 3 standard reflections every 200 reflections intensity decay: 1%

Refinement
  • R[F2 > 2[sigma](F2)] = 0.057

  • wR(F2) = 0.167

  • S = 1.00

  • 2326 reflections

  • 172 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.22 e Å-3

  • [Delta][rho]min = -0.14 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H1A...O3i 0.86 2.24 3.033 (3) 154
O3-H3B...O1 0.82 1.62 2.435 (3) 179
Symmetry code: (i) [x+{\script{1\over 2}}, -y+{\script{1\over 2}}, -z+1].

Data collection: CAD-4 EXPRESS (Enraf-Nonius, 1994[Enraf-Nonius (1994). CAD-4 EXPRESS. Enraf-Nonius, Delft, The Netherlands.]); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo,1995[Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany.]); program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: XU5724 ).


Acknowledgements

The authors thank the Center of Testing and Analysis, Nanjing University, for the data collection.

References

Enraf-Nonius (1994). CAD-4 EXPRESS. Enraf-Nonius, Delft, The Netherlands.
Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany.
Koch, C., Görls, H. & Westerhausen, M. (2008). Acta Cryst. E64, o2358.  [CSD] [CrossRef] [IUCr Journals]
Konshin, M. E., Syropyatov, B. Y., Vakhrin, M. I., Neifel'd, P. G., Feshin, V. P., Shurov, S. N. & Odegova1, T. F. (2010). Pharm. Chem. J. 44, 476-479.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]


Acta Cryst (2013). E69, o1520  [ doi:10.1107/S1600536813024483 ]

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