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

K N Venugopala; Susanta K Nayak; Thavendran Govender; Hendrik G Kruger; Glenn E M Maguire

doi:10.1107/S1600536812041888

. 2012 Oct 13;68(Pt 11):o3125. doi: 10.1107/S1600536812041888

(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, Glenn E M Maguire ^c

PMCID: PMC3515230 PMID: 23284450

Abstract

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—H⋯N bonds, further linked by C—H⋯O bonds and C—H⋯π and π–π 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,
a = 7.4598 (3) Å
b = 19.3131 (8) Å
c = 24.4002 (9) Å
V = 3515.4 (2) Å³
Z = 8
Mo Kα radiation
μ = 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 > 2σ(I)
R _int = 0.063

Refinement

R[F ² > 2σ(F ²)] = 0.059
wR(F ²) = 0.200
S = 1.30
3206 reflections
235 parameters
H-atom parameters constrained
Δρ_max = 0.66 e Å⁻³
Δρ_min = −0.33 e Å⁻³

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 Material

Click here for additional data file.^{(19.9KB, cif)}

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812041888/bg2479sup1.cif

e-68-o3125-sup1.cif^{(19.9KB, cif)}

Click here for additional data file.^{(157.4KB, hkl)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812041888/bg2479Isup2.hkl

e-68-o3125-Isup2.hkl^{(157.4KB, hkl)}

Click here for additional data file.^{(6.6KB, cml)}

Supplementary material file. DOI: 10.1107/S1600536812041888/bg2479Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

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

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C17—H17⋯N1ⁱ	0.95	2.56	3.432 (5)	153
C5—H5⋯O2ⁱⁱ	0.95	2.59	3.478 (5)	155
C18—H18⋯Cg1ⁱⁱⁱ	0.95	2.62	3.433 (5)	144

Open in a new tab

Symmetry codes: (i) Inline graphic ; (ii) ; (iii) .

Acknowledgments

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.

supplementary crystallographic information

Comment

Our interest in the molecular design of the benzothiazole moiety is due to its diverse chemical and biological activities. Benzothiazole derivatives exhibit biological activities as antitumor, antiinflammatory, analgesic, antimicrobial, and potential anti HIV agents etc. Still the variety of biological features of new benzothiazole derivatives are of great scientific interest Rana et al. (2007); Telvekar et al. (2012); Saeed et al. (2010). Here, we report the single-crystal structure of the title compound, C₂₁H₁₄ClNO₂S.

The molecule adopts a conformation with a 68.6 (2)° dihedral angle between the planes of the benzothiazole and diphenyl methanone groups (Fig. 1). The weak C—H···N hydrogen bonds (Table 1, 1st entry) form dimeric units (Fig. 2a), in turn linked by the C—H···O ones (Table 1, 2nd entry) into planar arrays parallel to (001). This 2D structure is reinforced by a C-H···π bond involving the five-membered ring S1/C1/C6/N1/C7 (centroid Cg1) (Table 1, third entry) and a π···π bond between the C10—C14 six-membered ring (centroid Cg2) and the C16—C21 six-membered ring (centroid Cg3), viz., Cg2···Cg3ⁱ, (i): 1/2 + x, 1/2 - y, -z, with an intercentroid distance of 3.856 (2) Å, all these interactions leading to the criss-cross assembly depicted in Fig 2b.

Experimental

To a solution of 2-(chloromethyl)-benzo-thiazole (0.5 g, 0.0027 mol) and (5-chloro-2-hydroxyphenyl)(phenyl)methanone (0.0027 mol) in dry THF, dry potassium carbonate (0.38 g, 0.0027 mol) was added and stirred at room temperature. The reaction mixture was concentrated to remove the solvent, diluted with ethyl acetate, washed with water, brine solution and dried over anhydrous sodium sulfate. The organic layer was concentrated to yield a residue which was purified by column chromatography using ethyl acetate and n-hexane as eluent (7:3, Rf = 0.68) to afford as a white solid product (Yield 70.8%; m. p. 403 (2) K).Suitable crystals for single-crystal X-ray study were obtained by slow evaporation crystallization from ethanol solvent at room temperature.