2-({[4-(1,3-Benzothia­zol-2-yl)phen­yl]amino}methyl)­phenol

Potgieter, K.; Gerber, T.; Hosten, E.; Betz, R.

doi:10.1107/S1600536811051580

Volume 68
Part 1
Page o27
January 2012

Received 3 November 2011
Accepted 30 November 2011
Online 3 December 2011

Key indicators
Single-crystal X-ray study
T = 200 K
Mean (C-C) = 0.002 Å
R = 0.033
wR = 0.092
Data-to-parameter ratio = 17.9
Details

2-({[4-(1,3-Benzothiazol-2-yl)phenyl]amino}methyl)phenol

Kim Potgieter,^a Thomas Gerber,^a Eric Hosten ^a and Richard Betz ^a ^*

^aNelson Mandela Metropolitan University, Summerstrand Campus, Department of Chemistry, University Way, Summerstrand, PO Box 77000, Port Elizabeth 6031, South Africa
Correspondence e-mail: richard.betz@webmail.co.za

In the title compound, C₂₀H₁₆N₂OS, the aniline substituent essentially coplanar with the benzothiazole moiety (with an r.m.s. deviation of all fitted non-H atoms of 0.0612 Å). The phenol group is almost perpendicular to the benzothiazolylaniline group, with an interplanar angle of 88.36 (2)°. In the crystal, molecules aggregate as centrosymmetric dimers by pairs of O-HN hydrogen bonds. C-HO contacts and N-H [pi] (arene) interactions also occur.

Related literature

For general information about rhenium-supported radio-pharmaceuticals, see: Gerber et al. (2011). For the crystal structure of 4-(1,3-benzothiazol-2-yl)-N-(2-pyridylmethyl)aniline monohydrate, see: Su et al. (2009). For graph-set analysis of hydrogen bonds, see: Etter et al. (1990); Bernstein et al. (1995).

Experimental

Crystal data

C₂₀H₁₆N₂OS
M_r = 332.41
Monoclinic, P 2₁ /c
a = 13.3260 (4) Å
b = 5.7940 (1) Å
c = 24.2246 (6) Å
= 121.546 (1)°
V = 1593.99 (7) Å³
Z = 4
Mo K radiation
= 0.21 mm^-1
T = 200 K
0.44 × 0.17 × 0.11 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2008) T_min = 0.929, T_max = 1.000
15126 measured reflections
3953 independent reflections
3272 reflections with I > 2(I)
R_int = 0.018

Refinement

R[F² > 2(F²)] = 0.033
wR(F²) = 0.092
S = 1.03
3953 reflections
221 parameters
H atoms treated by a mixture of independent and constrained refinement
_max = 0.30 e Å^-3
_min = -0.23 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C31-C36 ring.

D-HA	D-H	HA	DA	D-HA
O1-H1N1ⁱ	0.82	1.95	2.7459 (14)	164
C26-H26O1ⁱ	0.95	2.48	3.3645 (16)	156
N2-H72Cgⁱⁱ	0.82 (2)	2.61 (2)	3.4024 (14)	163.0 (19)
Symmetry codes: (i) -x, -y, -z; (ii) x, y+1, z.

Data collection: APEX2 (Bruker, 2010); cell refinement: SAINT (Bruker, 2010); data reduction: SAINT; program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: GG2063 ).

Acknowledgements

The authors thank Mr Jason Kopp for helpful discussions.

References

Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst. 32, 115-119.
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.
Bruker (2008). SADABS. Bruker Inc., Madison, Wisconsin, USA.
Bruker (2010). 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.
Gerber, T. I. A., Betz, R., Booysen, I. N., Potgieter, K. C. & Mayer, P. (2011). Polyhedron, 30, 1739-1745.
Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.
Su, Z.-H., Wang, Q.-Z., Teng, L. & Zhang, Y. (2009). Acta Cryst. E65, o86.

organic compounds