Mefenacet [2-(1,3-benzothia­zol-2-yl­oxy)-N-methyl-N-phenyl­acetamide]

Sanghun Cheon; Tae Ho Kim; Suk-Hee Moon; Jineun Kim

doi:10.1107/S1600536810044284

. 2010 Nov 13;66(Pt 12):o3153. doi: 10.1107/S1600536810044284

Mefenacet [2-(1,3-benzothiazol-2-yloxy)-N-methyl-N-phenylacetamide]

Sanghun Cheon ^a, Tae Ho Kim ^a,^*, Suk-Hee Moon ^b, Jineun Kim ^a,^*

PMCID: PMC3011531 PMID: 21589451

Abstract

The title compound, C₁₆H₁₄N₂O₂S, crystallizes with two independent molecules in the asymmetric unit. The dihedral angles between the plane of the benzothiazole ring system and the phenyl ring plane are 51.63 (7) and 60.46 (5)°. In the crystal structure, weak intermolecular C—H⋯O hydrogen bonds and C—H⋯π interactions contribute to the stabilization of the packing.

Related literature

For information on the toxicity and herbicidal properties of the title compound, see: Lu et al. (2001 ▶). For related structures, see: Murru et al. (2009 ▶).

Experimental

Crystal data

C₁₆H₁₄N₂O₂S
M _r = 298.35
Monoclinic,
a = 11.2708 (6) Å
b = 15.7112 (9) Å
c = 19.9579 (8) Å
β = 122.997 (2)°
V = 2964.0 (3) Å³
Z = 8
Mo Kα radiation
μ = 0.22 mm⁻¹
T = 173 K
0.19 × 0.17 × 0.09 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.959, T _max = 0.980
30345 measured reflections
7338 independent reflections
5174 reflections with I > 2σ(I)
R _int = 0.045

Refinement

R[F ² > 2σ(F ²)] = 0.042
wR(F ²) = 0.107
S = 1.02
7338 reflections
381 parameters
H-atom parameters constrained
Δρ_max = 0.27 e Å⁻³
Δρ_min = −0.28 e Å⁻³

Data collection: APEX2 (Bruker, 2006 ▶); cell refinement: SAINT (Bruker, 2006 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL and DIAMOND (Brandenburg, 1998 ▶); software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810044284/wn2417sup1.cif

e-66-o3153-sup1.cif^{(26.7KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810044284/wn2417Isup2.hkl

e-66-o3153-Isup2.hkl^{(359.1KB, hkl)}

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

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

Cg,1 Cg2 and Cg3 are the centroids of the C27–C32, C17–C22 and S1/C1/C6/N1/C7 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯O4ⁱ	0.95	2.44	3.273 (2)	147
C8—H8B⋯O3ⁱⁱ	0.99	2.43	3.235 (2)	138
C24—H24B⋯O2	0.99	2.35	3.256 (2)	153
C15—H15⋯Cg1ⁱⁱ	0.95	2.97	3.84	154
C26—H26B⋯Cg2ⁱⁱⁱ	0.98	3.00	3.74	134
C29—H29⋯Cg3^iv	0.95	2.95	3.74	141
C30—H30⋯Cg2ⁱ	0.95	2.80	3.42	124

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

Acknowledgments

This research was supported by the Basic Science Research Program through the National Research Foundation of Korea (NRF) funded by the Ministry of Education, Science and Technology (grant No. 2010-0016386).

supplementary crystallographic information

Comment

Mefenacet (systematic name: 2-(1,3-benzothiazol-2-yloxy)-N- methylacetanilide), is a type of herbicide with low toxicity and high activity (Lu et al. 2001). However its crystal structure has not hitherto been reported.

In the asymmetric unit (Fig. 1), the dihedral angles between the plane of the benzothiazole ring system and the phenyl ring plane are 51.63 (7)° and 60.46 (5)°. All bond lengths and bond angles are normal and comparable to those observed in similar crystal structures (Murru et al., 2009).

In the crystal structure, as shown in Fig. 2, weak intermolecular C—H···O hydrogen bonds and C—H···π interactions are observed (Table 1). These intermolecular interactions may contribute to the stabilization of the packing.

Experimental

The title compound was purchased from the Dr. Ehrenstorfer GmbH Company. Slow evaporation of a solution in CH₂Cl₂ gave single crystals suitable for X-ray analysis.