3-Hy­droxy-2-meth­oxy­benzamide

Wilbrand, S.; Neis, C.; Hegetschweiler, K.

doi:10.1107/S1600536812047769

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 (C-C) = 0.002 Å
R = 0.030
wR = 0.083
Data-to-parameter ratio = 12.2
Details

3-Hydroxy-2-methoxybenzamide

Sabine Wilbrand,^a Christian Neis ^a and Kaspar Hegetschweiler ^a ^*

^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-HO hydrogen bonds. Through intermolecular O-HO 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) and McMahon et al. (2005). A description of the Cambridge Crystallographic Database is given by Allen (2002). The question of the occurrence of very bent, intramolecular C-HO hydrogen bonds has been discussed by Desiraju (1996).

Experimental

Crystal data

C₈H₉NO₃
M_r = 167.16
Monoclinic, P 2₁ /n
a = 5.6293 (2) Å
b = 10.1826 (4) Å
c = 13.2402 (5) Å
= 92.750 (1)°
V = 758.07 (5) Å³
Z = 4
Mo K radiation
= 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) T_min = 0.947, T_max = 0.984
7200 measured reflections
1484 independent reflections
1325 reflections with I > 2(I)
R_int = 0.022

Refinement

R[F² > 2(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
_max = 0.27 e Å^-3
_min = -0.19 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1-H1AO3ⁱ	0.901 (17)	2.056 (17)	2.9547 (13)	175.3 (14)
N1-H1BO1	0.887 (17)	1.977 (17)	2.6789 (13)	135.0 (14)
O2-H2O3ⁱⁱ	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); cell refinement: SAINT (Bruker, 2010); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 2012); 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.
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.
Eccles, K. S., Elcoate, C. J., Maguire, A. R. & Lawrence, S. E. (2011). Cryst. Growth Des. 11, 4433-4439.
McMahon, J. A., Bis, J. A., Vishweshwar, P., Shattock, T. R., McLaughlin, O. L. & Zaworotko, M. J. (2005). Z. Kristallogr. 220, 340-350.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.

organic compounds