(2-Amino­phen­yl)methanol

Zipp, C.F.; Fernandes, M.A.; Marques, H.M.; Michael, J.P.

doi:10.1107/S1600536811053657

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 (C-C) = 0.003 Å
R = 0.030
wR = 0.075
Data-to-parameter ratio = 8.7
Details

(2-Aminophenyl)methanol

Caitlin F. Zipp,^a Manuel A. Fernandes,^a ^* Helder M. Marques ^a and Joseph P. Michael ^a

^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-HO hydrogen bonds which link molecules related by translation along the b axis, and O-HN and further N-HO 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). For the use of amines in crystal engineering, see: Bernstein et al. (1999). For hydrogen-bond motifs, see: Bernstein et al. (1995); Etter et al. (1990).

Experimental

Crystal data

C₇H₉NO
M_r = 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 radiation
= 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(I)
R_int = 0.078

Refinement

R[F² > 2(F²)] = 0.030
wR(F²) = 0.075
S = 1.09
715 reflections
82 parameters
1 restraint
H-atom parameters constrained
_max = 0.12 e Å^-3
_min = -0.13 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O1-H1N1ⁱ	0.85	1.94	2.791 (2)	172
N1-H1BO1ⁱ	0.91	2.28	3.135 (2)	156
N1-H1AO1ⁱⁱ	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); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and SCHAKAL99 (Keller, 1999); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

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.
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N. L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.
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.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.
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.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.

organic compounds