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Acta Crystallogr Sect E Struct Rep Online. 2010 December 1; 66(Pt 12): o3317.
Published online 2010 November 27. doi:  10.1107/S1600536810048051
PMCID: PMC3011397

4-(2-Sulfanyl­idene-1,3-benzothia­zol-3-yl)butan-2-one

Abstract

In the title compound, C11H11NOS2, the benzine ring is coplanar with the thia­zole ring, making a dihedral angle of 0.81 (1)°. In the crystal, adjacent mol­ecules are connected into a helical chain along the b axis by S(...)S contacts [3.4345 (18) Å]. These helical chains are further assembled into a three-dimensional supermolecular network by inter­molecular C—H(...)O hydrogen bond between aromatic ring H atoms and carbonyl groups.

Related literature

For a description of the Cambridge Structural Database, see: Allen (2002 [triangle]). For a related structure, see: Zhu et al. (2009 [triangle]). For S(...)S contacts, see: Dai et al. (1997 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-o3317-scheme1.jpg

Experimental

Crystal data

  • C11H11NOS2
  • M r = 237.33
  • Orthorhombic, An external file that holds a picture, illustration, etc.
Object name is e-66-o3317-efi1.jpg
  • a = 4.9457 (19) Å
  • b = 11.586 (4) Å
  • c = 19.830 (7) Å
  • V = 1136.3 (7) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.44 mm−1
  • T = 296 K
  • 0.23 × 0.19 × 0.15 mm

Data collection

  • Bruker APEXII CCD diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2006 [triangle]) T min = 0.905, T max = 0.936
  • 12565 measured reflections
  • 1476 independent reflections
  • 1176 reflections with I > 2σ(I)
  • R int = 0.036

Refinement

  • R[F 2 > 2σ(F 2)] = 0.043
  • wR(F 2) = 0.117
  • S = 1.07
  • 1476 reflections
  • 120 parameters
  • 2 restraints
  • H-atom parameters constrained
  • Δρmax = 0.27 e Å−3
  • Δρmin = −0.31 e Å−3

Data collection: APEX2 (Bruker, 2006 [triangle]); cell refinement: SAINT (Bruker, 2006 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXTL.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810048051/ds2068sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810048051/ds2068Isup2.hkl

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

supplementary crystallographic information

Experimental

A solution of benzothiazole-2-thiol (167.2 mg, 1.00 mmol) and in acetone (15 ml) was slowly added to a solution of CH2Cl2 (170.0 mg, 2.00 mmol) in acetone (15 ml). The resultant solution was stirred and refluxed for 16 h and then filtered. Colorless crystals suitable for X-ray diffraction were obtained in about two weeks by slow diffusion of diethyl ether into a dilute solution of the title compound in methanol. yield: ca 35.8% (based on benzothiazole-2-thiol).

Refinement

The structure was solved using direct methods followed by Fourier synthesis. Non-H atoms were refined anisotropically. All of H atoms were placed in idealized positions (C—H = 0.93, 0.96 or 0.97 Å), forced to ride on the atom to which they are bonded, and were included in the refinement in the riding-model approximation. Uiso values were set equal to 1.5Ueq(parent atom) for methylic H atom and to 1.2Ueq(parent atom)for all other H atoms. Friedel opposites were merged as the data could not resolve the absolute structure and consequently, the Flack paarameter was not reported.

Figures

Fig. 1.
The structure of the title compound with 50% probability displacement ellipsoids.
Fig. 2.
View of right-handle helical chain connected by S···S contacts along b axis.
Fig. 3.
View of three-dimensional supermolecular network connected by S···S contacts and C—H···O hydrogen bonds along the c direction.

Crystal data

C11H11NOS2F(000) = 496
Mr = 237.33Dx = 1.387 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 2911 reflections
a = 4.9457 (19) Åθ = 2.7–22.7°
b = 11.586 (4) ŵ = 0.44 mm1
c = 19.830 (7) ÅT = 296 K
V = 1136.3 (7) Å3Block, colorless
Z = 40.23 × 0.19 × 0.15 mm

Data collection

Bruker APEXII CCD diffractometer1476 independent reflections
Radiation source: fine-focus sealed tube1176 reflections with I > 2σ(I)
graphiteRint = 0.036
[var phi] and ω scansθmax = 27.0°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2006)h = −6→6
Tmin = 0.905, Tmax = 0.936k = −14→14
12565 measured reflectionsl = −25→25

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.043Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.117H-atom parameters constrained
S = 1.07w = 1/[σ2(Fo2) + (0.0535P)2 + 0.413P] where P = (Fo2 + 2Fc2)/3
1476 reflections(Δ/σ)max < 0.001
120 parametersΔρmax = 0.27 e Å3
2 restraintsΔρmin = −0.31 e Å3

Special details

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)

xyzUiso*/Ueq
C20.4190 (4)−0.16020 (16)0.16706 (8)0.0559 (8)
C30.5987 (5)−0.25022 (15)0.15525 (10)0.0688 (10)
H30.6161−0.30940.18660.083*
C40.7524 (5)−0.25173 (19)0.09657 (12)0.0762 (11)
H40.8726−0.31200.08870.091*
C50.7264 (5)−0.1632 (2)0.04970 (10)0.0727 (10)
H50.8293−0.16420.01040.087*
C60.5468 (5)−0.07320 (17)0.06150 (9)0.0635 (9)
H60.5294−0.01400.03010.076*
C70.3931 (4)−0.07169 (15)0.12018 (10)0.0517 (8)
S10.2105 (2)−0.13581 (7)0.23522 (4)0.0652 (2)
S2−0.1380 (2)0.07257 (8)0.23950 (6)0.0796 (3)
O10.0395 (7)0.3256 (2)0.04435 (16)0.0938 (9)
N10.2077 (6)0.0109 (2)0.13995 (13)0.0527 (6)
C10.0920 (7)−0.0080 (3)0.20141 (17)0.0563 (8)
C80.1402 (8)0.1127 (2)0.09994 (17)0.0595 (9)
H8A−0.04930.13120.10640.071*
H8B0.16700.09530.05260.071*
C90.3097 (8)0.2163 (3)0.11870 (18)0.0604 (9)
H9A0.29410.22950.16680.072*
H9B0.49780.19950.10890.072*
C100.2300 (5)0.3236 (2)0.08225 (17)0.0677 (7)
C110.3976 (7)0.4283 (2)0.09581 (18)0.0677 (7)
H11A0.32970.49190.06990.102*
H11B0.58180.41320.08330.102*
H11C0.38920.44690.14290.102*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
C20.0587 (19)0.0440 (15)0.0651 (18)−0.0037 (15)−0.0112 (17)−0.0018 (14)
C30.071 (2)0.0540 (17)0.081 (2)0.0062 (19)−0.015 (2)0.0014 (18)
C40.066 (2)0.0627 (19)0.100 (3)0.010 (2)−0.004 (2)−0.011 (2)
C50.068 (2)0.069 (2)0.081 (2)−0.005 (2)0.008 (2)−0.0089 (19)
C60.064 (2)0.0609 (18)0.066 (2)−0.0031 (19)−0.0016 (18)0.0002 (17)
C70.0539 (19)0.0446 (14)0.0566 (16)−0.0047 (15)−0.0070 (16)−0.0022 (13)
S10.0826 (6)0.0508 (4)0.0623 (4)−0.0036 (5)−0.0010 (5)0.0044 (4)
S20.0827 (7)0.0613 (5)0.0950 (6)−0.0010 (5)0.0162 (6)−0.0161 (5)
O10.0917 (17)0.0742 (15)0.115 (2)0.0104 (17)−0.0352 (14)0.0259 (16)
N10.0536 (15)0.0448 (12)0.0598 (14)−0.0007 (13)−0.0075 (14)0.0015 (11)
C10.0573 (19)0.0456 (15)0.0659 (18)−0.0085 (16)−0.0055 (18)−0.0084 (14)
C80.058 (2)0.0501 (15)0.0710 (19)0.0005 (16)−0.0130 (17)0.0067 (15)
C90.055 (2)0.0501 (16)0.076 (2)0.0044 (17)−0.0083 (19)0.0091 (15)
C100.0791 (17)0.0570 (12)0.0671 (14)0.0039 (15)−0.0077 (12)0.0097 (12)
C110.0791 (17)0.0570 (12)0.0671 (14)0.0039 (15)−0.0077 (12)0.0097 (12)

Geometric parameters (Å, °)

C2—C31.3900O1—C101.206 (4)
C2—C71.3900N1—C11.364 (4)
C2—S11.724 (2)N1—C81.460 (4)
C3—C41.3900C8—C91.511 (4)
C3—H30.9300C8—H8A0.9700
C4—C51.3900C8—H8B0.9700
C4—H40.9300C9—C101.491 (4)
C5—C61.3900C9—H9A0.9700
C5—H50.9300C9—H9B0.9700
C6—C71.3900C10—C111.494 (4)
C6—H60.9300C11—H11A0.9600
C7—N11.382 (3)C11—H11B0.9600
S1—C11.728 (3)C11—H11C0.9600
S2—C11.654 (4)
C3—C2—C7120.0N1—C1—S1110.0 (2)
C3—C2—S1129.62 (11)S2—C1—S1122.7 (2)
C7—C2—S1110.38 (11)N1—C8—C9112.4 (3)
C4—C3—C2120.0N1—C8—H8A109.1
C4—C3—H3120.0C9—C8—H8A109.1
C2—C3—H3120.0N1—C8—H8B109.1
C3—C4—C5120.0C9—C8—H8B109.1
C3—C4—H4120.0H8A—C8—H8B107.9
C5—C4—H4120.0C10—C9—C8113.4 (3)
C4—C5—C6120.0C10—C9—H9A108.9
C4—C5—H5120.0C8—C9—H9A108.9
C6—C5—H5120.0C10—C9—H9B108.9
C7—C6—C5120.0C8—C9—H9B108.9
C7—C6—H6120.0H9A—C9—H9B107.7
C5—C6—H6120.0O1—C10—C9121.6 (2)
N1—C7—C6127.51 (16)O1—C10—C11122.1 (3)
N1—C7—C2112.49 (16)C9—C10—C11116.3 (3)
C6—C7—C2120.0C10—C11—H11A109.5
C2—S1—C192.25 (14)C10—C11—H11B109.5
C1—N1—C7114.8 (2)H11A—C11—H11B109.5
C1—N1—C8121.3 (3)C10—C11—H11C109.5
C7—N1—C8123.8 (3)H11A—C11—H11C109.5
N1—C1—S2127.3 (3)H11B—C11—H11C109.5
C7—C2—C3—C40.0C2—C7—N1—C11.5 (3)
S1—C2—C3—C4−178.85 (17)C6—C7—N1—C80.9 (4)
C2—C3—C4—C50.0C2—C7—N1—C8−179.6 (2)
C3—C4—C5—C60.0C7—N1—C1—S2−179.4 (2)
C4—C5—C6—C70.0C8—N1—C1—S21.7 (5)
C5—C6—C7—N1179.5 (2)C7—N1—C1—S1−1.8 (3)
C5—C6—C7—C20.0C8—N1—C1—S1179.3 (2)
C3—C2—C7—N1−179.6 (2)C2—S1—C1—N11.2 (2)
S1—C2—C7—N1−0.53 (18)C2—S1—C1—S2178.9 (2)
C3—C2—C7—C60.0C1—N1—C8—C985.9 (4)
S1—C2—C7—C6179.05 (14)C7—N1—C8—C9−93.0 (3)
C3—C2—S1—C1178.56 (17)N1—C8—C9—C10−175.5 (3)
C7—C2—S1—C1−0.38 (15)C8—C9—C10—O13.4 (5)
C6—C7—N1—C1−178.0 (2)C8—C9—C10—C11−177.1 (3)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C11—H11B···O1i0.962.603.541 (5)167

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: DS2068).

References

  • Allen, F. H. (2002). Acta Cryst. B58, 380–388. [PubMed]
  • Bruker (2006). APEX2, SAINT and SADABS Bruker AXS Inc., Madison, Wisconsin, USA.
  • Dai, J., Munakata, M., Wu, L.-P., Kuroda-Sowa, T. & Suenaga, Y. (1997). Inorg. Chim. Acta, 258, 65–69.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Zhu, J.-Q., Fang, H.-C., Chen, B.-Y., Feng, M.-S. & Li, J.-N. (2009). Acta Cryst. E65, o1640. [PMC free article] [PubMed]

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