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Volume 69 
Part 6 
Page o930  
June 2013  

Received 25 April 2013
Accepted 15 May 2013
Online 22 May 2013

Key indicators
Single-crystal X-ray study
T = 120 K
Mean [sigma](C-C) = 0.002 Å
R = 0.044
wR = 0.111
Data-to-parameter ratio = 12.5
Details
Open access

N-(2-Methoxyphenyl)phthalamic acid

aCavendish Laboratory, University of Cambridge, J. J. Thomson Avenue, Cambridge CB3 0HE, England
Correspondence e-mail: jmc61@cam.ac.uk

The title compound, C14H13NO3, adopts a twisted conformation in the crystal, with an interplanar angle between the two benzene rings of 87.30 (5)°. Molecules within the structure are linked via O-H...O interactions, forming a hydrogen-bonded chain motif with graph set C(7) along the glide plane in the [001] direction.

Related literature

For related phthalamic acid structures, see: Smith et al. (1983[Smith, G., Kennard, C. H. L. & Katekar, G. F. (1983). Aust. J. Chem. 36, 2455-2463.]) and Bocelli et al. (1989[Bocelli, G., Rizzoli, C. & Ori, O. (1989). Z. Kristallogr. 189, 301-316.]). For the structure of a diaryl amide containing the 2-methoxyphenyl moeity, see: Parra et al. (2001[Parra, R. D., Zeng, H., Zhu, J., Zheng, C., Zeng, X. C. & Gong, B. (2001). Chem. Eur. J. 7, 4352-4357.]). A description of hydrogen bonding in terms of graph sets is given by Etter (1990[Etter, M. C. (1990). Acc. Chem. Res. 23, 121-126.]) and Bernstein et al. (1995)[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]. For standard bond lengths as calculated using crystal structure data, see Allen et al. (2006[Allen, F. H., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (2006). International Tables for Crystallography, Vol. C, ch. 9.5, pp. 790-811. International Union of Crystallography.]).

[Scheme 1]

Experimental

Crystal data
  • C15H13NO4

  • Mr = 271.26

  • Monoclinic, P 21 /c

  • a = 9.038 (4) Å

  • b = 14.237 (5) Å

  • c = 10.405 (4) Å

  • [beta] = 107.456 (5)°

  • V = 1277.2 (9) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.10 mm-1

  • T = 120 K

  • 0.53 × 0.18 × 0.09 mm

Data collection
  • Rigaku Saturn724+ diffractometer

  • Absorption correction: multi-scan (ABSCOR; Higashi, 1995[Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan.]) Tmin = 0.978, Tmax = 0.991

  • 9056 measured reflections

  • 2904 independent reflections

  • 2687 reflections with I > 2[sigma](I)

  • Rint = 0.034

Refinement
  • R[F2 > 2[sigma](F2)] = 0.044

  • wR(F2) = 0.111

  • S = 1.09

  • 2904 reflections

  • 233 parameters

  • All H-atom parameters refined

  • [Delta][rho]max = 0.30 e Å-3

  • [Delta][rho]min = -0.20 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O1-H1O...O3i 0.97 (3) 1.72 (3) 2.6837 (16) 175 (2)
Symmetry code: (i) [x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}].

Data collection: CrystalClear-SM Expert (Rigaku, 2009[Rigaku (2009). CrystalClear-SM Expert. Rigaku Corporation, The Woodlands, Texas, USA.]); cell refinement: CrystalClear-SM Expert; data reduction: CrystalClear-SM Expert; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: WinGX (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: GW2134 ).


Acknowledgements

JMC thanks the Royal Society for a University Research Fellowship, the University of New Brunswick for the UNB Vice-Chancellor's Research Chair, and NSERC for the Discovery Grant 355708 (for PGW).

References

Allen, F. H., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (2006). International Tables for Crystallography, Vol. C, ch. 9.5, pp. 790-811. International Union of Crystallography.
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.  [CrossRef] [ChemPort] [ISI]
Bocelli, G., Rizzoli, C. & Ori, O. (1989). Z. Kristallogr. 189, 301-316.  [CrossRef] [ChemPort]
Etter, M. C. (1990). Acc. Chem. Res. 23, 121-126.  [CrossRef] [ISI]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan.
Parra, R. D., Zeng, H., Zhu, J., Zheng, C., Zeng, X. C. & Gong, B. (2001). Chem. Eur. J. 7, 4352-4357.  [CrossRef] [PubMed] [ChemPort]
Rigaku (2009). CrystalClear-SM Expert. Rigaku Corporation, The Woodlands, Texas, USA.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]
Smith, G., Kennard, C. H. L. & Katekar, G. F. (1983). Aust. J. Chem. 36, 2455-2463.  [CrossRef] [ChemPort]


Acta Cryst (2013). E69, o930  [ doi:10.1107/S1600536813013408 ]

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