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Volume 69 
Part 5 
Page o738  
May 2013  

Received 7 April 2013
Accepted 9 April 2013
Online 17 April 2013

Key indicators
Single-crystal X-ray study
T = 100 K
Mean [sigma](C-C) = 0.006 Å
R = 0.059
wR = 0.192
Data-to-parameter ratio = 9.2
Details
Open access

4-Hydroxy-N-methylbenzamide

aDepartment of Chemistry, Keene State College, 229 Main Street, Keene, NH 03435-2001, USA,bDepartment of Chemistry, Howard University, 525 College Street NW, Washington, DC 20059, USA,cDepartment of Studies in Chemistry, Mangalore University, Mangalagangotri 574 199, India,dDepartment of Studies in Chemistry, University of Mysore, Manasagangotri, Mysore 570 006, India, and eDepartment of Chemistry, P.A. College of Engineering, Nadupadavu, Mangalore 574 153, India
Correspondence e-mail: jjasinski@keene.edu

Three independent molecules comprise the asymmetric unit of the title compound, C8H9NO2, in which the dihedral angles between the amide group and the benzene ring are 3.0 (2), 4.0 (3) and 3.3 (9)°. In the crystal, O-H...O hydrogen bonds and weak C-H...N interactions are observed, forming infinite chains along [101].

Related literature

For background to the biological activity of aromatic amides, see: Saeed et al. (2008[Saeed, A., Khera, R. A., Abbas, N., Simpson, J. & Stanley, R. G. (2008). Acta Cryst. E64, o2322-o2323.]); Brunsveld et al. (2001[Brunsveld, L., Folmer, B. J. B., Meijer, E. W. & Sijbesma, R. P. (2001). Chem. Rev. 101, 4071-4097.]); Prins et al. (2001[Prins, L. J., Peinhoudt, D. N. & Timmerman, P. (2001). Angew. Chem. Int. Ed. 40, 2383-2426.]). For the anti-emetic activity of N-substituted benzamides, see: Vega-Noverola et al. (1989[Vega-Noverola, A. P., Soto, J. M., Noguera, F. P., Mauri, J. M. & Spickett, G. W. R. (1989). US Patent No. 4877780.]). For related structures, see: Escalada et al. (2004[Escalada, J., Freedman, D. & Werner, E. J. (2004). Acta Cryst. E60, o1296-o1298.]); Pertlik (1992[Pertlik, F. (1992). Z. Kristallogr. 202, 17-23.]). For standard bond lengths, see: Allen et al. (1987[Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.]).

[Scheme 1]

Experimental

Crystal data
  • C8H9NO2

  • Mr = 151.16

  • Monoclinic, C c

  • a = 13.576 (3) Å

  • b = 16.964 (3) Å

  • c = 11.025 (2) Å

  • [beta] = 120.11 (3)°

  • V = 2196.5 (10) Å3

  • Z = 12

  • Mo K[alpha] radiation

  • [mu] = 0.10 mm-1

  • T = 100 K

  • 0.42 × 0.28 × 0.22 mm

Data collection
  • Agilent Xcalibur diffractometer with a Ruby (Gemini Cu) detector

  • Absorption correction: multi-scan (CrysAlis PRO and CrysAlis RED; Agilent, 2012[Agilent (2012). CrysAlis PRO and CrysAlis RED. Agilent Technologies, Yarnton, England.]) Tmin = 0.634, Tmax = 1.000

  • 4810 measured reflections

  • 2802 independent reflections

  • 2545 reflections with I > 2[sigma](I)

  • Rint = 0.015

Refinement
  • R[F2 > 2[sigma](F2)] = 0.059

  • wR(F2) = 0.192

  • S = 1.10

  • 2802 reflections

  • 305 parameters

  • 2 restraints

  • H-atom parameters constrained

  • [Delta][rho]max = 0.58 e Å-3

  • [Delta][rho]min = -0.56 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O1A-H1A...O2Ci 0.82 1.94 2.749 (5) 170
C2A-H2A...N1Aii 0.93 2.66 3.267 (5) 124
C4A-H4A...N1Bi 0.93 2.60 3.371 (5) 141
O1B-H1B...O2Biii 0.82 1.98 2.784 (5) 166
C2B-H2B...N1Ciii 0.93 2.63 3.404 (5) 142
O1C-H1C...O2A 0.82 1.96 2.750 (5) 163
Symmetry codes: (i) x-1, y, z-1; (ii) [x, -y+1, z+{\script{1\over 2}}]; (iii) [x+{\script{1\over 2}}, -y+{\script{3\over 2}}, z+{\script{1\over 2}}].

Data collection: CrysAlis PRO (Agilent, 2012[Agilent (2012). CrysAlis PRO and CrysAlis RED. Agilent Technologies, Yarnton, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL2012 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: OLEX2 (Dolomanov et al., 2009[Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339-341.]); software used to prepare material for publication: OLEX2.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HG5306 ).


Acknowledgements

BN thanks Mangalore University and the UGC SAP for financial assistance for the purchase of chemicals. HSY thanks the UOM for sabbatical leave. RJB acknowledges the NSF MRI program (grant No. CHE-0619278) for funds to purchase the X-ray diffractometer.

References

Agilent (2012). CrysAlis PRO and CrysAlis RED. Agilent Technologies, Yarnton, England.
Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.
Brunsveld, L., Folmer, B. J. B., Meijer, E. W. & Sijbesma, R. P. (2001). Chem. Rev. 101, 4071-4097.  [ISI] [CrossRef] [PubMed] [ChemPort]
Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339-341.  [ISI] [CrossRef] [ChemPort] [details]
Escalada, J., Freedman, D. & Werner, E. J. (2004). Acta Cryst. E60, o1296-o1298.  [CSD] [CrossRef] [ChemPort] [details]
Pertlik, F. (1992). Z. Kristallogr. 202, 17-23.  [CrossRef] [ChemPort]
Prins, L. J., Peinhoudt, D. N. & Timmerman, P. (2001). Angew. Chem. Int. Ed. 40, 2383-2426.
Saeed, A., Khera, R. A., Abbas, N., Simpson, J. & Stanley, R. G. (2008). Acta Cryst. E64, o2322-o2323.  [CSD] [CrossRef] [ChemPort] [details]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]
Vega-Noverola, A. P., Soto, J. M., Noguera, F. P., Mauri, J. M. & Spickett, G. W. R. (1989). US Patent No. 4877780.


Acta Cryst (2013). E69, o738  [ doi:10.1107/S1600536813009781 ]

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