organic compounds
2-(1,3-Benzothiazol-2-ylsulfanyl)-N-(2-methylphenyl)acetamide
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
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
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Refinement
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Data collection: CrystalClear (Rigaku/MSC, 2005); cell 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
10.1107/S1600536812042109/cv5340sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536812042109/cv5340Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536812042109/cv5340Isup3.cml
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).
Atom H1 attached to N atom was located on a difference map and refined isotropically. Other H atoms were positioned geometrically (C—H = 0.95–0.99 Å), and refined as riding, with Uiso(H) = 1.2–1.5Ueq(C).
Data collection: CrystalClear (Rigaku/MSC, 2005); cell
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).Fig. 1. View of the molecule of (I) showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 60% probability level. |
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 |
C16H14N2OS2 | V = 1438.3 (4) Å3 |
Mr = 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)° |
Rigaku Saturn CCD area-detector diffractometer | 3421 independent reflections |
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005) | 2923 reflections with I > 2σ(I) |
Tmin = 0.923, Tmax = 0.978 | Rint = 0.055 |
14718 measured reflections |
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 | Δρmax = 0.33 e Å−3 |
3421 reflections | Δρmin = −0.27 e Å−3 |
195 parameters |
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) |
Symmetry code: (i) x+1, y, z. |
Experimental details
Crystal data | |
Chemical formula | C16H14N2OS2 |
Mr | 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) |
Tmin, Tmax | 0.923, 0.978 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 14718, 3421, 2923 |
Rint | 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 |
Δρmax, Δρmin (e Å−3) | 0.33, −0.27 |
Computer programs: CrystalClear (Rigaku/MSC, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).
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
Fallah-Tafti, A., Foroumadi, A., Tiwari, R., Shirazi, A. N., Hangauer, D. G., Bu, Y., Akbarzadeh, T., Parang, K. & Shafiee, A. (2011). Eur. J. Med. Chem. 46, 4853–4858. Web of Science CAS PubMed Google Scholar
Gao, Y., Liang, D., Gao, L.-X., Fang, G.-J. & Wang, W. (2007). Acta Cryst. E63, o4854. Web of Science CSD CrossRef IUCr Journals Google Scholar
Rigaku/MSC (2005). CrystalClear. Molecular Structure Corporation, The Woodlands, Texas, USA, and Rigaku Corporation, Tokyo, Japan. Google Scholar
Shams, H. Z., Mohareb, R. M., Helal, M. H. & Mahmoud, A. (2011). Molecules, 16, 52–73. Web of Science CrossRef CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Zhao, B., Wang, H., Li, Q., Gao, Y. & Liang, D. (2009). Acta Cryst. E65, o958. Web of Science CSD CrossRef IUCr Journals Google Scholar
This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
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 Csp2—S bond [S1—C10 = 1.745 (2) Å] is significantly shorter than the Csp3—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.