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Volume 68 
Part 12 
Page o3494  
December 2012  

Received 30 October 2012
Accepted 20 November 2012
Online 30 November 2012

Key indicators
Single-crystal X-ray study
T = 110 K
Mean [sigma](C-C) = 0.002 Å
R = 0.030
wR = 0.083
Data-to-parameter ratio = 12.2
Details
Open access

3-Hydroxy-2-methoxybenzamide

aFachrichtung Chemie, Universität des Saarlandes, Postfach 151150, D-66041 Saarbrücken, Germany
Correspondence e-mail: hegetschweiler@mx.uni-saarland.de

The crystal structure of the title compound, C8H9NO3, features centrosymmetric dimers with two amide groups interconnected by a pair of almost linear N-H...O hydrogen bonds. Through intermolecular O-H...O interactions between phenolic hydroxy groups and carbonyl O atoms, these dimers are assembled into undulating hydrogen-bonded layers parallel to the [101] plane. Additionally, the anti-H(-N) atom of the primary amide group forms an intramolecular hydrogen bond to the O atom of the methoxy group. The amide group froms a dihedral angle of 12.6 (1)° with the phenyl ring.

Related literature

Hydrogen-bonding packing patterns of primary amides are discussed by Eccles et al. (2011[Eccles, K. S., Elcoate, C. J., Maguire, A. R. & Lawrence, S. E. (2011). Cryst. Growth Des. 11, 4433-4439.]) and McMahon et al. (2005[McMahon, J. A., Bis, J. A., Vishweshwar, P., Shattock, T. R., McLaughlin, O. L. & Zaworotko, M. J. (2005). Z. Kristallogr. 220, 340-350.]). A description of the Cambridge Crystallographic Database is given by Allen (2002[Allen, F. H. (2002). Acta Cryst. B58, 380-388.]). The question of the occurrence of very bent, intramolecular C-H...O hydrogen bonds has been discussed by Desiraju (1996[Desiraju, G. R. (1996). Acc. Chem. Res. 29, 441-449.]).

[Scheme 1]

Experimental

Crystal data
  • C8H9NO3

  • Mr = 167.16

  • Monoclinic, P 21 /n

  • a = 5.6293 (2) Å

  • b = 10.1826 (4) Å

  • c = 13.2402 (5) Å

  • [beta] = 92.750 (1)°

  • V = 758.07 (5) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.11 mm-1

  • T = 110 K

  • 0.49 × 0.18 × 0.14 mm

Data collection
  • Bruker APEXII KappaCCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2010[Bruker (2010). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.947, Tmax = 0.984

  • 7200 measured reflections

  • 1484 independent reflections

  • 1325 reflections with I > 2[sigma](I)

  • Rint = 0.022

Refinement
  • R[F2 > 2[sigma](F2)] = 0.030

  • wR(F2) = 0.083

  • S = 1.06

  • 1484 reflections

  • 122 parameters

  • H atoms treated by a mixture of independent and constrained refinement

  • [Delta][rho]max = 0.27 e Å-3

  • [Delta][rho]min = -0.19 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H1A...O3i 0.901 (17) 2.056 (17) 2.9547 (13) 175.3 (14)
N1-H1B...O1 0.887 (17) 1.977 (17) 2.6789 (13) 135.0 (14)
O2-H2...O3ii 0.88 (2) 1.83 (2) 2.6895 (12) 165.5 (17)
Symmetry codes: (i) -x+1, -y+2, -z+1; (ii) [x-{\script{1\over 2}}, -y+{\script{3\over 2}}, z+{\script{1\over 2}}].

Data collection: APEX2 (Bruker, 2010[Bruker (2010). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2010[Bruker (2010). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; 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: DIAMOND (Brandenburg, 2012[Brandenburg, K. (2012). DIAMOND. Crystal Impact GbR, Bonn, Germany.]); software used to prepare material for publication: SHELXL97.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: LD2083 ).


Acknowledgements

We thank Dr Volker Huch (Universität des Saarlandes) for the data collection.

References

Allen, F. H. (2002). Acta Cryst. B58, 380-388.  [ISI] [CrossRef] [details]
Brandenburg, K. (2012). DIAMOND. Crystal Impact GbR, Bonn, Germany.
Bruker (2010). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Desiraju, G. R. (1996). Acc. Chem. Res. 29, 441-449.  [CrossRef] [ChemPort] [ISI]
Eccles, K. S., Elcoate, C. J., Maguire, A. R. & Lawrence, S. E. (2011). Cryst. Growth Des. 11, 4433-4439.  [CrossRef] [ChemPort]
McMahon, J. A., Bis, J. A., Vishweshwar, P., Shattock, T. R., McLaughlin, O. L. & Zaworotko, M. J. (2005). Z. Kristallogr. 220, 340-350.  [CrossRef] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]


Acta Cryst (2012). E68, o3494  [ doi:10.1107/S1600536812047769 ]

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