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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 [sigma](C-C) = 0.002 Å
R = 0.033
wR = 0.092
Data-to-parameter ratio = 17.9
Details
Open access

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

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-H...N hydrogen bonds. C-H...O contacts and N-H...[pi](arene) interactions also occur.

Related literature

For general information about rhenium-supported radio-pharmaceuticals, see: Gerber et al. (2011[Gerber, T. I. A., Betz, R., Booysen, I. N., Potgieter, K. C. & Mayer, P. (2011). Polyhedron, 30, 1739-1745.]). For the crystal structure of 4-(1,3-benzothiazol-2-yl)-N-(2-pyridylmethyl)aniline monohydrate, see: Su et al. (2009[Su, Z.-H., Wang, Q.-Z., Teng, L. & Zhang, Y. (2009). Acta Cryst. E65, o86.]). For graph-set analysis of hydrogen bonds, see: Etter et al. (1990[Etter, M. C., MacDonald, J. C. & Bernstein, J. (1990). Acta Cryst. B46, 256-262.]); Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]).

[Scheme 1]

Experimental

Crystal data
  • C20H16N2OS

  • Mr = 332.41

  • Monoclinic, P 21 /c

  • a = 13.3260 (4) Å

  • b = 5.7940 (1) Å

  • c = 24.2246 (6) Å

  • [beta] = 121.546 (1)°

  • V = 1593.99 (7) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 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[Bruker (2008). SADABS. Bruker Inc., Madison, Wisconsin, USA.]) Tmin = 0.929, Tmax = 1.000

  • 15126 measured reflections

  • 3953 independent reflections

  • 3272 reflections with I > 2[sigma](I)

  • Rint = 0.018

Refinement
  • R[F2 > 2[sigma](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

  • [Delta][rho]max = 0.30 e Å-3

  • [Delta][rho]min = -0.23 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C31-C36 ring.

D-H...A D-H H...A D...A D-H...A
O1-H1...N1i 0.82 1.95 2.7459 (14) 164
C26-H26...O1i 0.95 2.48 3.3645 (16) 156
N2-H72...Cgii 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[Bruker (2010). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2010[Bruker (2010). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SIR97 (Altomare et al., 1999[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.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]) and Mercury (Macrae et al., 2008[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.]); software used to prepare material for publication: SHELXL97 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: 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.  [ISI] [CrossRef] [ChemPort] [details]
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.  [CrossRef] [ChemPort] [ISI]
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.  [CrossRef] [ISI] [details]
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  [CrossRef] [details]
Gerber, T. I. A., Betz, R., Booysen, I. N., Potgieter, K. C. & Mayer, P. (2011). Polyhedron, 30, 1739-1745.  [ISI] [CSD] [CrossRef] [ChemPort]
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.  [ISI] [CrossRef] [ChemPort] [details]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]
Su, Z.-H., Wang, Q.-Z., Teng, L. & Zhang, Y. (2009). Acta Cryst. E65, o86.  [CSD] [CrossRef] [details]


Acta Cryst (2012). E68, o27  [ doi:10.1107/S1600536811051580 ]

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