2-(Benzo[d]thia­zol-2-ylsulfan­yl)-N-(6-methyl-2-pyrid­yl)acetamide

Bing Zhao; Hui Wang; Qiang Li; Yan Gao; Dong Liang

doi:10.1107/S1600536809011519

. 2009 Apr 2;65(Pt 5):o958. doi: 10.1107/S1600536809011519

2-(Benzo[d]thiazol-2-ylsulfanyl)-N-(6-methyl-2-pyridyl)acetamide

Bing Zhao ^a,^*, Hui Wang ^b, Qiang Li ^c, Yan Gao ^c, Dong Liang ^c

PMCID: PMC2977658 PMID: 21584001

Abstract

In the title compound, C₁₅H₁₃N₃OS₂, the pyridine ring and the benzo[d]thiazole unit subtend a dihedral angle of 57.7 (2)°. The length of the C_sp ²—S bond [1.7462 (17) Å] is significantly shorter than that of the C_sp ³—S bond [1.8133 (18) Å]. The crystal structure is stabilized by intramolecular N—H⋯N and intermolecular C—H⋯O and C—H⋯N hydrogen-bond interactions. Furthermore, C—H⋯π interactions stabilize the crystal packing.

Related literature

For biologically active compounds containing the acylamide system, see: Bennasar et al. (2006 ▶); Ladziata et al. (2006 ▶). For bond-length data, see: Gao et al. (2007 ▶).

Experimental

Crystal data

C₁₅H₁₃N₃OS₂
M _r = 315.40
Triclinic,
a = 8.1919 (16) Å
b = 9.0818 (18) Å
c = 11.107 (2) Å
α = 74.78 (3)°
β = 89.55 (3)°
γ = 69.34 (3)°
V = 742.8 (3) Å³
Z = 2
Mo Kα radiation
μ = 0.36 mm⁻¹
T = 113 K
0.16 × 0.14 × 0.10 mm

Data collection

Rigaku Saturn diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.945, T _max = 0.965
9391 measured reflections
3526 independent reflections
2615 reflections with I > 2σ(I)
R _int = 0.048

Refinement

R[F ² > 2σ(F ²)] = 0.037
wR(F ²) = 0.092
S = 0.99
3526 reflections
195 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.24 e Å⁻³
Δρ_min = −0.38 e Å⁻³

Data collection: CrystalClear (Molecular Structure Corporation & Rigaku, 1999 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809011519/at2753sup1.cif

e-65-0o958-sup1.cif^{(18.7KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809011519/at2753Isup2.hkl

e-65-0o958-Isup2.hkl^{(172.9KB, hkl)}

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

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

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯N3	0.867 (18)	2.142 (18)	2.949 (2)	154.6 (16)
C2—H2⋯O1	0.95	2.30	2.890 (2)	119
C8—H8A⋯O1ⁱ	0.99	2.31	3.239 (2)	156
C8—H8B⋯N3	0.99	2.47	2.905 (2)	106
C12—H12⋯N1ⁱⁱ	0.95	2.57	3.498 (2)	166
C8—H8B⋯Cg2ⁱⁱⁱ	0.99	2.68	3.494 (2)	140

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Symmetry codes: (i) Inline graphic ; (ii) ; (iii) . Cg2 is the centroid of the N1/C1–C5 ring.

Acknowledgments

The project was supported by the Initial Fund for Young Teachers of Qiqihar University (000203).

supplementary crystallographic information

Comment

The acylamide compound is an important class of medical intermediate. Recently, many biological compounds containing acylamide have been reported (Ladziata et al., 2006; Bennasar et al., 2006). Now, we have synthesized the title compound, (I), from the benzo[d]thiazole-2-thiol with 6-methylpyridine carbamic chloride. Here, we report its crystal structure.

The molecular structure of (I) and the atom-numbering scheme are shown in Fig. 1. The molecule contains a pyridine ring and a benzo[d]thiazole ring. The dihedral angle between the benzene ring and benzo[d]thiazole ring is 57.7 (2)°. The methyl carbon attached to the pyridine ring is coplanar to the pyridine ring with an r.m.s deviation of 0.0064 (3) Å. The C1—N1—C7—C8 torsion angle of 178.66 (15)° indicates that the acylamide group are nearly coplanar with the pyridine ring plane. As a result of π-π conjugation, the C_sp²—S bond [S1—C9 = 1.7462 (17) Å] is significantly shorter than the C_sp³—S bond [S1—C8 = 1.8133 (18) Å]. These values compare with the values of 1.772 (3) and 1.801 (2) Å reported in the literature (Gao et al., 2007). The crystal structure is stabilized by the intramolecular N—H···N and intermolecular C—H···O and C—H···N hydrogen bond interactions. Furthermore, C—H···π interactions stabilize the crystal packing (Table 1).

Experimental

The title compound was synthesized by the reaction of from the benzo[d]thiazole-2-thiol with 6-methylpyridine carbamic chloride in the refluxing ethanol. Crystals of (I) suitable for single-crystal X-ray analysis were grown by slow evaporation of a solution in chloroform/acetone.