(2-(Benzo[d]thia­zol-2yl-meth­oxy)-5-chloro­phen­yl)(phen­yl)methanone

Venugopala, K.N.; Nayak, S.K.; Govender, T.; Kruger, H.G.; Maguire, G.E.M.

doi:10.1107/S1600536812041888

Volume 68
Part 11
Page o3125
November 2012

Received 21 August 2012
Accepted 6 October 2012
Online 13 October 2012

Key indicators
Single-crystal X-ray study
T = 173 K
Mean (C-C) = 0.006 Å
R = 0.059
wR = 0.200
Data-to-parameter ratio = 13.6
Details

(2-(Benzo[d]thiazol-2yl-methoxy)-5-chlorophenyl)(phenyl)methanone

K. N. Venugopala,^a ^* Susanta K. Nayak,^b ^* Thavendran Govender,^a Hendrik G. Kruger ^c and Glenn E. M. Maguire ^c

^aSchool of Pharmacy and Pharmacology, University of KwaZulu-Natal, Durban 4000, South Africa,^bCenter for Nano Science and Technology@Polimi, Istituto Italiano di Tecnologia, Via Pascoli 70/3-20133 Milan, Italy, and ^cSchool of Chemistry and Physics, University of KwaZulu-Natal, Durban 4000, South Africa
Correspondence e-mail: venugopala@ukzn.ac.za, nksusa@gmail.com

In the title compound, C₂₁H₁₄ClNO₂S, the dihedral angle between the benzothiazole and diphenyl methanone groups is 68.6 (2)°. The crystal structure consists of dimeric units generated by C-HN bonds, further linked by C-HO bonds and C-H [pi] and [pi] - [pi] interactions [centroid-centroiddistance = 3.856 (2) Å], which lead to a criss-cross assembly parallel to (001).

Related literature

For background to the applications of benzothiazole derivatives, see: Rana et al. (2007); Telvekar et al. (2012); Saeed et al. (2010).

Experimental

Crystal data

C₂₁H₁₄ClNO₂S
M_r = 379.84
Orthorhombic, P b c a
a = 7.4598 (3) Å
b = 19.3131 (8) Å
c = 24.4002 (9) Å
V = 3515.4 (2) Å³
Z = 8
Mo K radiation
= 0.35 mm^-1
T = 173 K
0.22 × 0.16 × 0.03 mm

Data collection

Nonius KappaCCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2008) T_min = 0.927, T_max = 0.990
52834 measured reflections
3206 independent reflections
2576 reflections with I > 2(I)
R_int = 0.063

Refinement

R[F² > 2(F²)] = 0.059
wR(F²) = 0.200
S = 1.30
3206 reflections
235 parameters
H-atom parameters constrained
_max = 0.66 e Å^-3
_min = -0.33 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the S1/C1/C6/N1/C7 ring.

D-HA	D-H	HA	DA	D-HA
C17-H17N1ⁱ	0.95	2.56	3.432 (5)	153
C5-H5O2ⁱⁱ	0.95	2.59	3.478 (5)	155
C18-H18Cg1ⁱⁱⁱ	0.95	2.62	3.433 (5)	144
Symmetry codes: (i) -x+1, -y, -z+1; (ii) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, z]$ ; (iii) x+1, y, z.

Data collection: COLLECT (Nonius, 1998); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997); data reduction: DENZO-SMN; 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 Mercury (Macrae et al., 2008); software used to prepare material for publication: PLATON (Spek, 2009) and PARST (Nardelli, 1995).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BG2479 ).

Acknowledgements

The authors wish to thank the University of KwaZulu-Natal, South Africa, for facilities and Dr Hong Su, Department of Chemistry, University of Cape Town, for the data collection.

References

Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
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.
Nardelli, M. (1995). J. Appl. Cryst. 28, 659.
Nonius (1998). COLLECT. Nonius BV, Delft, The Netherlands.
Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.
Rana, A., Siddiqui, N. & Khan, S. A. (2007). J. Pharm. Sci. 69, 10-17.
Saeed, S., Rashid, N., Jones, P. G., Ali, M. & Hussain, R. (2010). Eur. J. Med. Chem. 45, 1323-1331.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.
Telvekar, V. N., Bairwa, V. K., Satardekar, K. & Bellubi, A. (2012). Bioorg. Med. Chem. Lett. 22, 148-155.

organic compounds