2-(1,3-Benzothiazol-2-ylsulfanyl)-N-(2-methylphenyl)acetamide

Sun, Y.; Wang, X.-J.; Zheng, P.-W.

doi:10.1107/S1600536812042109

organic compounds

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ISSN: 2056-9890

Volume 68| Part 11| November 2012| Page o3138

doi:10.1107/S1600536812042109

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2-(1,3-Benzothiazol-2-ylsulfanyl)-N-(2-methylphenyl)acetamide

Yue Sun,^a Xiao-Jun Wang ^b and Peng-Wu Zheng ^a ^*

^aSchool of Pharmacy, Jiangxi Science and Technology Normal University, Nanchang 330013, People's Republic of China, and ^bPolytechnic Institute of Jiangxi Science and Technology Normal University, Nanchang 330013, People's Republic of China
^*Correspondence e-mail: zhengpw@126.com

(Received 9 September 2012; accepted 8 October 2012; online 20 October 2012)

In the title molecule, C₁₆H₁₄N₂OS₂, the benzene ring and the benzo[d]thiazole mean plane form a dihedral angle of 75.5 (1)°. The acetamide group is twisted by 47.7 (1)° from the attached benzene ring. In the crystal, molecules related by translation along the a axis are linked into chains through N—H⋯O hydrogen bonds.

Related literature

For the crystal structures of similar compounds, see: Gao et al. (2007 ); Zhao et al. (2009 ). For the medical activity of heterocyclic derivatives containing the acetamide group, see: Fallah-Tafti et al. (2011 ); Shams et al. (2011 )

Experimental

Crystal data

C₁₆H₁₄N₂OS₂
M_r = 314.41
Monoclinic, P 2₁ /n
a = 4.7957 (8) Å
b = 27.496 (4) Å
c = 10.9906 (13) Å
β = 97.048 (4)°
V = 1438.3 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.37 mm⁻¹
T = 113 K
0.22 × 0.06 × 0.06 mm

Data collection

Rigaku Saturn CCD area-detector diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005 ) T_min = 0.923, T_max = 0.978
14718 measured reflections
3421 independent reflections
2923 reflections with I > 2σ(I)
R_int = 0.055

Refinement

R[F² > 2σ(F²)] = 0.048
wR(F²) = 0.100
S = 1.06
3421 reflections
195 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.33 e Å⁻³
Δρ_min = −0.27 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1ⁱ	0.81 (2)	2.10 (2)	2.906 (2)	168 (2)
Symmetry code: (i) x+1, y, z.

Data collection: CrystalClear (Rigaku/MSC, 2005); 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: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812042109/cv5340sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812042109/cv5340Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812042109/cv5340Isup3.cml

checkCIF report

Comment top

Acylamide compounds have gained widely attention due to their the important medical activity. Recently, the synthesis and medical activities of some heterocyclic derivatives containing the acylamide moiety have been reported (Fallah-Tafti et al., 2011; Shams et al., 2011). Now the title compound, 2-(benzo[d]thiazol-2-ylthio)-N-o-tolylacetamide, was synthesized and its crystal structure was reported.

The molecular structure of title compound and the atom-mumbering scheme are shown in Fig. 1. The molecule contain a benzene ring and benzo[d]thiazole ring. The dihedral angle between the benzene ring and benzo[d]thiazole ring is 75.5°. The acetamide group is twisted at 47.7 (1)° from the attached benzene ring. C1 atom attached to the benzene ring is coplanar to the benzene ring with an r.m.s deviation of 0.0046 Å. As a result of π–π conjugation, the C_sp²—S bond [S1—C10 = 1.745 (2) Å] is significantly shorter than the C_sp³—S bond [S1—C9 = 1.812 (2) Å]. These values compare with the values of 1.772 (3) and 1.801 (2) Å reported in the literature (Gao et al., 2007; Zhao et al., 2009).

The crystal structure is stablized by the intermolecular N—H···O hydrogen bond (Table 1) interaction.

Related literature top

For the crystal structures of similar compounds, see: Gao et al. (2007); Zhao et al. (2009). For the medical activity of heterocyclic derivatives containing the acetamide group, see: Fallah-Tafti et al. (2011); Shams et al. (2011)

Experimental top

The title compound was synthesized by the reaction of the benzo[d]thiazol-2-thiol with 2-methylphenyl 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–ethanol (1:1).

Computing details top

Data collection: CrystalClear (Rigaku/MSC, 2005); cell refinement: CrystalClear (Rigaku/MSC, 2005); data reduction: CrystalClear (Rigaku/MSC, 2005); 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: SHELXL97 (Sheldrick, 2008).

Figures top

Fig. 1. View of the molecule of (I) showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 60% probability level.

2-(1,3-Benzothiazol-2-ylsulfanyl)-N-(2-methylphenyl)acetamide top

Crystal data top

C₁₆H₁₄N₂OS₂	F(000) = 656
M_r = 314.41	D_x = 1.452 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 4445 reflections
a = 4.7957 (8) Å	θ = 1.5–27.9°
b = 27.496 (4) Å	µ = 0.37 mm⁻¹
c = 10.9906 (13) Å	T = 113 K
β = 97.048 (4)°	Prism, colourless
V = 1438.3 (4) Å³	0.22 × 0.06 × 0.06 mm
Z = 4

Data collection top

Rigaku Saturn CCD area-detector diffractometer	3421 independent reflections
Radiation source: rotating anode	2923 reflections with I > 2σ(I)
Multilayer monochromator	R_int = 0.055
Detector resolution: 14.22 pixels mm^-1	θ_max = 27.9°, θ_min = 1.5°
ϕ and ω scans	h = −6→6
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005)	k = −36→36
T_min = 0.923, T_max = 0.978	l = −14→14
14718 measured reflections

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.100	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ²(F_o²) + (0.0351P)² + 0.5795P] where P = (F_o² + 2F_c²)/3
3421 reflections	(Δ/σ)_max = 0.001
195 parameters	Δρ_max = 0.33 e Å⁻³
0 restraints	Δρ_min = −0.27 e Å⁻³

Crystal data top

C₁₆H₁₄N₂OS₂	V = 1438.3 (4) Å³
M_r = 314.41	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 4.7957 (8) Å	µ = 0.37 mm⁻¹
b = 27.496 (4) Å	T = 113 K
c = 10.9906 (13) Å	0.22 × 0.06 × 0.06 mm
β = 97.048 (4)°

Data collection top

Rigaku Saturn CCD area-detector diffractometer	3421 independent reflections
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005)	2923 reflections with I > 2σ(I)
T_min = 0.923, T_max = 0.978	R_int = 0.055
14718 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.048	0 restraints
wR(F²) = 0.100	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	Δρ_max = 0.33 e Å⁻³
3421 reflections	Δρ_min = −0.27 e Å⁻³
195 parameters

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
S1	0.48672 (11)	0.112141 (18)	0.29125 (5)	0.02069 (14)
S2	0.16105 (11)	0.158557 (18)	0.47479 (5)	0.01966 (14)
O1	0.1342 (3)	0.09883 (5)	0.03414 (14)	0.0233 (3)
N1	0.5406 (4)	0.08369 (6)	−0.04653 (15)	0.0162 (4)
N2	0.1583 (3)	0.19259 (6)	0.25292 (15)	0.0168 (3)
C1	0.6969 (4)	0.10401 (7)	−0.2868 (2)	0.0224 (5)
H1A	0.7119	0.1064	−0.3747	0.034*
H1B	0.8819	0.0965	−0.2424	0.034*
H1C	0.6295	0.1350	−0.2573	0.034*
C2	0.4933 (4)	0.06418 (7)	−0.26509 (18)	0.0170 (4)
C3	0.3715 (4)	0.03516 (7)	−0.36122 (19)	0.0212 (4)
H3	0.4183	0.0407	−0.4416	0.025*
C4	0.1835 (4)	−0.00162 (7)	−0.3421 (2)	0.0230 (5)
H4	0.1010	−0.0206	−0.4092	0.028*
C5	0.1159 (4)	−0.01059 (7)	−0.2249 (2)	0.0216 (4)
H5	−0.0119	−0.0359	−0.2115	0.026*
C6	0.2356 (4)	0.01747 (7)	−0.12783 (19)	0.0181 (4)
H6	0.1916	0.0112	−0.0473	0.022*
C7	0.4210 (4)	0.05501 (7)	−0.14794 (18)	0.0157 (4)
C8	0.3912 (4)	0.10278 (7)	0.03867 (18)	0.0174 (4)
C9	0.5622 (4)	0.13057 (7)	0.14044 (18)	0.0203 (4)
H9A	0.5228	0.1658	0.1296	0.024*
H9B	0.7645	0.1254	0.1346	0.024*
C10	0.2600 (4)	0.15837 (7)	0.32579 (18)	0.0171 (4)
C11	−0.0382 (4)	0.21033 (7)	0.43540 (18)	0.0172 (4)
C12	−0.2001 (4)	0.23768 (8)	0.50696 (19)	0.0221 (4)
H12	−0.2147	0.2290	0.5896	0.026*
C13	−0.3391 (4)	0.27784 (8)	0.4536 (2)	0.0243 (5)
H13	−0.4518	0.2970	0.5004	0.029*
C14	−0.3167 (4)	0.29069 (8)	0.3323 (2)	0.0243 (5)
H14	−0.4140	0.3185	0.2980	0.029*
C15	−0.1551 (4)	0.26352 (7)	0.26125 (19)	0.0217 (4)
H15	−0.1412	0.2724	0.1786	0.026*
C16	−0.0131 (4)	0.22287 (7)	0.31355 (18)	0.0157 (4)
H1	0.710 (5)	0.0869 (8)	−0.034 (2)	0.019 (6)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0214 (3)	0.0197 (3)	0.0205 (3)	0.0055 (2)	0.0010 (2)	−0.0037 (2)
S2	0.0230 (3)	0.0202 (3)	0.0161 (3)	0.0031 (2)	0.0038 (2)	0.00153 (19)
O1	0.0109 (7)	0.0304 (8)	0.0289 (9)	−0.0010 (6)	0.0032 (6)	−0.0092 (7)
N1	0.0101 (8)	0.0202 (9)	0.0186 (9)	−0.0016 (7)	0.0025 (7)	−0.0035 (7)
N2	0.0168 (8)	0.0176 (8)	0.0163 (8)	0.0011 (6)	0.0029 (7)	−0.0007 (7)
C1	0.0207 (11)	0.0236 (11)	0.0238 (11)	−0.0007 (8)	0.0068 (9)	0.0036 (9)
C2	0.0151 (10)	0.0168 (9)	0.0193 (10)	0.0035 (7)	0.0032 (8)	0.0004 (8)
C3	0.0252 (11)	0.0211 (10)	0.0175 (10)	0.0063 (8)	0.0026 (9)	0.0001 (8)
C4	0.0268 (11)	0.0177 (10)	0.0223 (11)	0.0021 (8)	−0.0059 (9)	−0.0055 (8)
C5	0.0179 (10)	0.0170 (10)	0.0292 (12)	−0.0022 (8)	0.0003 (9)	−0.0004 (9)
C6	0.0156 (10)	0.0184 (10)	0.0205 (10)	0.0009 (8)	0.0032 (8)	0.0015 (8)
C7	0.0129 (9)	0.0148 (9)	0.0191 (10)	0.0031 (7)	0.0003 (8)	−0.0021 (8)
C8	0.0156 (10)	0.0167 (9)	0.0199 (10)	0.0000 (8)	0.0027 (8)	−0.0022 (8)
C9	0.0139 (10)	0.0233 (10)	0.0243 (11)	−0.0013 (8)	0.0051 (9)	−0.0074 (8)
C10	0.0151 (9)	0.0182 (9)	0.0178 (10)	−0.0023 (8)	0.0019 (8)	−0.0027 (8)
C11	0.0158 (10)	0.0177 (9)	0.0179 (10)	0.0000 (8)	0.0017 (8)	−0.0015 (8)
C12	0.0214 (11)	0.0269 (11)	0.0189 (10)	0.0001 (9)	0.0070 (9)	−0.0041 (9)
C13	0.0196 (11)	0.0253 (11)	0.0284 (12)	0.0023 (9)	0.0050 (9)	−0.0088 (9)
C14	0.0229 (11)	0.0201 (10)	0.0294 (12)	0.0062 (8)	0.0010 (9)	−0.0004 (9)
C15	0.0226 (11)	0.0217 (10)	0.0215 (11)	0.0025 (8)	0.0056 (9)	0.0026 (8)
C16	0.0137 (9)	0.0159 (9)	0.0179 (10)	−0.0013 (7)	0.0027 (8)	−0.0021 (7)

Geometric parameters (Å, º) top

S1—C10	1.745 (2)	C4—H4	0.9500
S1—C9	1.812 (2)	C5—C6	1.383 (3)
S2—C11	1.739 (2)	C5—H5	0.9500
S2—C10	1.760 (2)	C6—C7	1.398 (3)
O1—C8	1.232 (2)	C6—H6	0.9500
N1—C8	1.353 (2)	C8—C9	1.511 (3)
N1—C7	1.427 (2)	C9—H9A	0.9900
N1—H1	0.81 (2)	C9—H9B	0.9900
N2—C10	1.292 (2)	C11—C12	1.392 (3)
N2—C16	1.395 (2)	C11—C16	1.402 (3)
C1—C2	1.505 (3)	C12—C13	1.382 (3)
C1—H1A	0.9800	C12—H12	0.9500
C1—H1B	0.9800	C13—C14	1.396 (3)
C1—H1C	0.9800	C13—H13	0.9500
C2—C3	1.394 (3)	C14—C15	1.385 (3)
C2—C7	1.397 (3)	C14—H14	0.9500
C3—C4	1.388 (3)	C15—C16	1.395 (3)
C3—H3	0.9500	C15—H15	0.9500
C4—C5	1.388 (3)

C10—S1—C9	101.26 (9)	O1—C8—N1	123.37 (18)
C11—S2—C10	88.47 (9)	O1—C8—C9	121.60 (17)
C8—N1—C7	123.97 (16)	N1—C8—C9	115.02 (16)
C8—N1—H1	116.7 (16)	C8—C9—S1	112.61 (14)
C7—N1—H1	119.1 (16)	C8—C9—H9A	109.1
C10—N2—C16	109.77 (16)	S1—C9—H9A	109.1
C2—C1—H1A	109.5	C8—C9—H9B	109.1
C2—C1—H1B	109.5	S1—C9—H9B	109.1
H1A—C1—H1B	109.5	H9A—C9—H9B	107.8
C2—C1—H1C	109.5	N2—C10—S1	126.43 (15)
H1A—C1—H1C	109.5	N2—C10—S2	116.76 (14)
H1B—C1—H1C	109.5	S1—C10—S2	116.81 (11)
C3—C2—C7	117.84 (18)	C12—C11—C16	121.74 (18)
C3—C2—C1	121.07 (18)	C12—C11—S2	128.98 (16)
C7—C2—C1	121.10 (18)	C16—C11—S2	109.27 (14)
C4—C3—C2	121.46 (19)	C13—C12—C11	117.73 (19)
C4—C3—H3	119.3	C13—C12—H12	121.1
C2—C3—H3	119.3	C11—C12—H12	121.1
C3—C4—C5	119.99 (19)	C12—C13—C14	121.17 (19)
C3—C4—H4	120.0	C12—C13—H13	119.4
C5—C4—H4	120.0	C14—C13—H13	119.4
C6—C5—C4	119.65 (19)	C15—C14—C13	121.1 (2)
C6—C5—H5	120.2	C15—C14—H14	119.5
C4—C5—H5	120.2	C13—C14—H14	119.5
C5—C6—C7	120.11 (19)	C14—C15—C16	118.57 (19)
C5—C6—H6	119.9	C14—C15—H15	120.7
C7—C6—H6	119.9	C16—C15—H15	120.7
C2—C7—C6	120.93 (18)	N2—C16—C15	124.56 (18)
C2—C7—N1	119.92 (17)	N2—C16—C11	115.72 (17)
C6—C7—N1	119.15 (17)	C15—C16—C11	119.72 (17)

C7—C2—C3—C4	0.2 (3)	C9—S1—C10—N2	6.5 (2)
C1—C2—C3—C4	−179.95 (18)	C9—S1—C10—S2	−173.28 (11)
C2—C3—C4—C5	−0.9 (3)	C11—S2—C10—N2	−0.15 (16)
C3—C4—C5—C6	0.4 (3)	C11—S2—C10—S1	179.60 (12)
C4—C5—C6—C7	0.7 (3)	C10—S2—C11—C12	−179.2 (2)
C3—C2—C7—C6	0.9 (3)	C10—S2—C11—C16	0.11 (15)
C1—C2—C7—C6	−178.92 (17)	C16—C11—C12—C13	0.5 (3)
C3—C2—C7—N1	179.88 (17)	S2—C11—C12—C13	179.73 (16)
C1—C2—C7—N1	0.1 (3)	C11—C12—C13—C14	−0.3 (3)
C5—C6—C7—C2	−1.4 (3)	C12—C13—C14—C15	0.2 (3)
C5—C6—C7—N1	179.61 (17)	C13—C14—C15—C16	−0.2 (3)
C8—N1—C7—C2	134.3 (2)	C10—N2—C16—C15	179.80 (19)
C8—N1—C7—C6	−46.7 (3)	C10—N2—C16—C11	−0.1 (2)
C7—N1—C8—O1	−3.0 (3)	C14—C15—C16—N2	−179.45 (18)
C7—N1—C8—C9	178.09 (17)	C14—C15—C16—C11	0.4 (3)
O1—C8—C9—S1	50.5 (2)	C12—C11—C16—N2	179.32 (17)
N1—C8—C9—S1	−130.60 (16)	S2—C11—C16—N2	−0.1 (2)
C10—S1—C9—C8	−100.06 (15)	C12—C11—C16—C15	−0.5 (3)
C16—N2—C10—S1	−179.59 (14)	S2—C11—C16—C15	−179.92 (15)
C16—N2—C10—S2	0.1 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1ⁱ	0.81 (2)	2.10 (2)	2.906 (2)	168 (2)

Symmetry code: (i) x+1, y, z.

Experimental details

Crystal data
Chemical formula	C₁₆H₁₄N₂OS₂
M_r	314.41
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	113
a, b, c (Å)	4.7957 (8), 27.496 (4), 10.9906 (13)
β (°)	97.048 (4)
V (Å³)	1438.3 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.37
Crystal size (mm)	0.22 × 0.06 × 0.06

Data collection
Diffractometer	Rigaku Saturn CCD area-detector diffractometer
Absorption correction	Multi-scan (CrystalClear; Rigaku/MSC, 2005)
T_min, T_max	0.923, 0.978
No. of measured, independent and observed [I > 2σ(I)] reflections	14718, 3421, 2923
R_int	0.055
(sin θ/λ)_max (Å⁻¹)	0.658

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.048, 0.100, 1.06
No. of reflections	3421
No. of parameters	195
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.33, −0.27

Computer programs: CrystalClear (Rigaku/MSC, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1ⁱ	0.81 (2)	2.10 (2)	2.906 (2)	168 (2)

Symmetry code: (i) x+1, y, z.

Acknowledgements

Support from the Science and Technology Project of Jiangxi Provincial Office of Eduction (grant No. GJJ11008) and the Science and Technology Project of Jiangxi Provincial Department of Science and Technology (grant No. 20111BBE50009) is gratefully acknowledged.

References

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