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Volume 68 
Part 1 
Page o174  
January 2012  

Received 11 November 2011
Accepted 13 December 2011
Online 21 December 2011

Key indicators
Single-crystal X-ray study
T = 173 K
Mean [sigma](C-C) = 0.003 Å
R = 0.030
wR = 0.075
Data-to-parameter ratio = 8.7
Details
Open access

(2-Aminophenyl)methanol

aMolecular Sciences Institute, School of Chemistry, University of the Witwatersrand, PO Wits 2050, Johannesburg, South Africa
Correspondence e-mail: manuel.fernandes@wits.ac.za

The crystal strucure of the title compound, C7H9NO, displays N-H...O hydrogen bonds which link molecules related by translation along the b axis, and O-H...N and further N-H...O hydrogen bonds which link molecules related by the 21 screw axis along the c axis. The resulting combination is a hydrogen-bonded layer of molecules parallel to (011).

Related literature

For the use of amines in the pharmaceutical industry, see: Morissette et al. (2004[Morissette, S. L., Almarsson, O., Peterson, M. L., Remenar, J. F., Read, M. J., Lemmo, A. V., Ellis, S., Cima, M. J. & Gardner, C. R. (2004). Adv. Drug Deliv. Rev. 56, 275-300.]). For the use of amines in crystal engineering, see: Bernstein et al. (1999[Bernstein, J., Davey, R. J. & Henck, J.-O. (1999). Angew. Chem. Int. Ed. Engl. 38, 3440-3461.]). For hydrogen-bond motifs, see: Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N. L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]); Etter et al. (1990[Etter, M. C., MacDonald, J. C. & Bernstein, J. (1990). Acta Cryst. B46, 256-262.]).

[Scheme 1]

Experimental

Crystal data
  • C7H9NO

  • Mr = 123.15

  • Orthorhombic, P n a 21

  • a = 22.6222 (9) Å

  • b = 6.0675 (2) Å

  • c = 4.7005 (2) Å

  • V = 645.19 (4) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.09 mm-1

  • T = 173 K

  • 0.46 × 0.20 × 0.07 mm

Data collection
  • Bruker APEXII CCD diffractometer

  • 4682 measured reflections

  • 715 independent reflections

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

  • Rint = 0.078

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

  • wR(F2) = 0.075

  • S = 1.09

  • 715 reflections

  • 82 parameters

  • 1 restraint

  • H-atom parameters constrained

  • [Delta][rho]max = 0.12 e Å-3

  • [Delta][rho]min = -0.13 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O1-H1...N1i 0.85 1.94 2.791 (2) 172
N1-H1B...O1i 0.91 2.28 3.135 (2) 156
N1-H1A...O1ii 0.87 2.19 3.0585 (17) 175
Symmetry codes: (i) [-x+1, -y+1, z-{\script{1\over 2}}]; (ii) x, y-1, z.

Data collection: APEX2 (Bruker, 2005[Bruker (2005). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2005[Bruker (2005). APEX2 and SAINT. 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: ORTEP-3 for Windows (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]) and SCHAKAL99 (Keller, 1999[Keller, E. (1999). SCHAKAL99. University of Freiberg, Germany.]); software used to prepare material for publication: WinGX (Farrugia, 1999[Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.]) and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: FJ2480 ).


Acknowledgements

This work was supported by the National Research Foundation, Pretoria (NRF, GUN 2053652 & 77122), the South African Research Chairs Initiative and the University of the Witwatersrand.

References

Bernstein, J., Davey, R. J. & Henck, J.-O. (1999). Angew. Chem. Int. Ed. Engl. 38, 3440-3461.  [CrossRef] [PubMed]
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N. L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.  [CrossRef] [ChemPort] [ISI]
Bruker (2005). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Etter, M. C., MacDonald, J. C. & Bernstein, J. (1990). Acta Cryst. B46, 256-262.  [CrossRef] [ISI] [details]
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  [CrossRef] [details]
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.  [CrossRef] [ChemPort] [details]
Keller, E. (1999). SCHAKAL99. University of Freiberg, Germany.
Morissette, S. L., Almarsson, O., Peterson, M. L., Remenar, J. F., Read, M. J., Lemmo, A. V., Ellis, S., Cima, M. J. & Gardner, C. R. (2004). Adv. Drug Deliv. Rev. 56, 275-300.  [CrossRef] [PubMed] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]


Acta Cryst (2012). E68, o174  [ doi:10.1107/S1600536811053657 ]

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