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

In the title mol-ecule, C(16)H(14)N(2)OS(2), the benzene ring and the benzo[d]thia-zole 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, mol-ecules 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 = 314.41

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.100

S = 1.06

3421 reflections

195 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.33 e Å−3

Δρmin = −0.27 e Å−3

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.

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812042109/cv5340sup1.cif

Click here for additional data file.

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

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536812042109/cv5340Isup3.cml

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

C16H14N2OS2	F(000) = 656
Mr = 314.41	Dx = 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

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

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(Fo2) + (0.0351P)2 + 0.5795P] where P = (Fo2 + 2Fc2)/3
3421 reflections	(Δ/σ)max = 0.001
195 parameters	Δρmax = 0.33 e Å−3
0 restraints	Δρmin = −0.27 e Å−3

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.

	x	y	z	Uiso*/Ueq
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)*

	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)

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)

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)

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) .