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Acta Crystallogr Sect E Struct Rep Online. 2009 February 1; 65(Pt 2): o440.
Published online 2009 January 31. doi:  10.1107/S1600536809003456
PMCID: PMC2968210

1,3-Dimethyl­benzo[b]dibenzothio­phene

Abstract

The molecule of the title compound, C18H14S, is approximately planar (r.m.s. deviation = 0.029 Å). The crystal packing is stabilized by weak inter­molecular C—H(...)π inter­actions.

Related literature

For the pharmacological activities of thio­phen derivatives, see: Dzhurayev et al. (1992 [triangle]); El-Maghraby et al. (1984 [triangle]); Gewald et al. (1996 [triangle]). For related structures, see: Harrison et al. (2006 [triangle]); Palani et al. (2006 [triangle]). For bond-length data, see: Allen et al. (1987 [triangle]).

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Object name is e-65-0o440-scheme1.jpg

Experimental

Crystal data

  • C18H14S
  • M r = 262.35
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-0o440-efi1.jpg
  • a = 10.0219 (3) Å
  • b = 5.8692 (5) Å
  • c = 22.8554 (5) Å
  • β = 99.787 (1)°
  • V = 1324.80 (12) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.23 mm−1
  • T = 295 (2) K
  • 0.26 × 0.20 × 0.18 mm

Data collection

  • Bruker Kappa APEXII diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.944, T max = 0.961
  • 27929 measured reflections
  • 3030 independent reflections
  • 2574 reflections with I > 2σ(I)
  • R int = 0.029

Refinement

  • R[F 2 > 2σ(F 2)] = 0.046
  • wR(F 2) = 0.137
  • S = 1.08
  • 3030 reflections
  • 174 parameters
  • H-atom parameters constrained
  • Δρmax = 0.26 e Å−3
  • Δρmin = −0.29 e Å−3

Data collection: APEX2 (Bruker, 2004 [triangle]); cell refinement: SAINT (Bruker, 2004 [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: PLATON (Spek, 2003 [triangle]); software used to prepare material for publication: SHELXL97.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809003456/bt2861sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809003456/bt2861Isup2.hkl

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

supplementary crystallographic information

Comment

Thiophen derivatives possess pharmacological activities such as anti-bacterial, anti-cancer, anti-inflammatory (El-Maghraby et al., 1984; Dzhurayev et al., 1992) and anti-toxic properties (Gewald et al., 1996).

The geometric parameters of the title molecule (Fig. 1) agree well with related structures (Harrison et al., 2006; Palani et al., 2006) and literature values (Allen et al., 1987). All non-H atoms lie in a common plane (r.m.s. deviation 0.029Å) .

The crystal packing is stabilized by weak intermolecular C - H···π [C17—H17C···Cg1 (1 - x, -y, 1 - z), H17C···Cg1 = 2.68 Å, C18—H18A··· Cg2 (1 + x, y, z), H18A···Cg1 = 2.75 Å; Cg1 and Cg2 are the centroid of rings defined by atoms C7/C8/C9/C14/C15/C16 and C1—C6, respectively) interactions. No significant intra- and intermolecular hydrogen bonds are observed.

Experimental

To a solution of diethyl 2-((2-(bromomethyl)banzo[b]thiophen-3-yl) methylene)malonate (0.35 g, 0.88 mmol) in dry 1,2-DCE (15 ml), ZnBr2 (0.39 g, 1.73 mmol) and m-xylene (0.13 ml, 1.03 mmol), were added. The reaction mixture was then refluxed for 2 h under N2 atmosphere. It was then poured over ice-water (50 ml) containing 2 ml of conc.HCl, extracted with chloroform (3 X 10 ml) and dried (Na2SO4). The removal of solvent followed by flash column chromatographic purification (silica gel, 230–420 mesh, n-hexane/ethyl acetate 99:1) afforded 1,3-dimethylbenzo[2,3-b] dibenzothiophene as a colourless crystal.

Refinement

H atoms were positioned geometrically and refined using a riding model with C—H = 0.93 Å and Uiso(H) = 1.2Ueq(C) for aromatic H atoms and C—H = 0.96 Å and Uiso(H) = 1.5Ueq(C) for methyl H atoms.

Figures

Fig. 1.
The molecular structure of (I), with atom labels and 50% probability displacement ellipsoids for non-H atoms.

Crystal data

C18H14SF(000) = 552
Mr = 262.35Dx = 1.315 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 6370 reflections
a = 10.0219 (3) Åθ = 2.1–27.4°
b = 5.8692 (5) ŵ = 0.23 mm1
c = 22.8554 (5) ÅT = 295 K
β = 99.787 (1)°Block, colourless
V = 1324.80 (12) Å30.26 × 0.20 × 0.18 mm
Z = 4

Data collection

Bruker Kappa APEXII diffractometer3030 independent reflections
Radiation source: fine-focus sealed tube2574 reflections with I > 2σ(I)
graphiteRint = 0.029
ω and [var phi] scansθmax = 27.5°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −13→13
Tmin = 0.944, Tmax = 0.961k = −7→7
27929 measured reflectionsl = −29→29

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)] = 0.046Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.137H-atom parameters constrained
S = 1.08w = 1/[σ2(Fo2) + (0.0636P)2 + 0.5697P] where P = (Fo2 + 2Fc2)/3
3030 reflections(Δ/σ)max < 0.001
174 parametersΔρmax = 0.26 e Å3
0 restraintsΔρmin = −0.29 e Å3

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

xyzUiso*/Ueq
C10.07838 (18)−0.0783 (3)0.33166 (8)0.0456 (4)
C2−0.0587 (2)−0.0829 (4)0.30694 (10)0.0567 (5)
H2−0.1153−0.19530.31770.068*
C3−0.1081 (2)0.0813 (4)0.26653 (9)0.0603 (6)
H3−0.19930.08010.24960.072*
C4−0.0245 (2)0.2490 (4)0.25047 (9)0.0579 (5)
H4−0.05990.35890.22280.069*
C50.1110 (2)0.2546 (3)0.27511 (8)0.0494 (5)
H50.16670.36780.26410.059*
C60.16390 (17)0.0909 (3)0.31632 (7)0.0403 (4)
C70.30153 (17)0.0662 (3)0.34821 (7)0.0378 (4)
C80.41378 (18)0.1971 (3)0.34603 (7)0.0408 (4)
H80.40710.32280.32090.049*
C90.53930 (17)0.1436 (3)0.38139 (7)0.0390 (4)
C100.65545 (19)0.2770 (3)0.37964 (8)0.0472 (4)
H100.64900.40270.35450.057*
C110.77693 (19)0.2268 (3)0.41376 (9)0.0480 (4)
C120.78456 (18)0.0376 (3)0.45225 (8)0.0477 (4)
H120.86740.00370.47570.057*
C130.67622 (18)−0.0979 (3)0.45659 (8)0.0419 (4)
C140.54908 (17)−0.0488 (3)0.41992 (7)0.0381 (4)
C150.43329 (18)−0.1822 (3)0.42159 (8)0.0437 (4)
H150.4381−0.30860.44640.052*
C160.31376 (18)−0.1253 (3)0.38656 (8)0.0418 (4)
C170.6892 (2)−0.2914 (4)0.49988 (9)0.0523 (5)
H17A0.7795−0.29440.52220.078*
H17B0.6709−0.43240.47870.078*
H17C0.6256−0.27140.52650.078*
C180.9007 (2)0.3703 (4)0.41279 (11)0.0648 (6)
H18A0.95980.29410.39020.097*
H18B0.94710.39350.45270.097*
H18C0.87420.51490.39490.097*
S10.16072 (5)−0.26890 (9)0.38419 (3)0.0592 (2)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
C10.0419 (9)0.0449 (10)0.0474 (9)−0.0078 (8)0.0001 (7)−0.0003 (8)
C20.0429 (10)0.0597 (12)0.0632 (12)−0.0153 (9)−0.0030 (9)0.0030 (10)
C30.0429 (10)0.0772 (15)0.0557 (11)−0.0015 (10)−0.0060 (8)−0.0008 (10)
C40.0542 (11)0.0668 (14)0.0491 (11)0.0049 (10)−0.0018 (9)0.0105 (9)
C50.0511 (10)0.0519 (11)0.0442 (9)−0.0012 (8)0.0053 (8)0.0069 (8)
C60.0406 (9)0.0429 (9)0.0367 (8)−0.0034 (7)0.0042 (7)−0.0033 (7)
C70.0391 (8)0.0378 (8)0.0361 (8)−0.0034 (7)0.0054 (6)−0.0014 (6)
C80.0425 (9)0.0404 (9)0.0393 (8)−0.0059 (7)0.0068 (7)0.0049 (7)
C90.0388 (8)0.0408 (9)0.0383 (8)−0.0050 (7)0.0089 (6)−0.0013 (7)
C100.0447 (10)0.0488 (10)0.0494 (10)−0.0102 (8)0.0120 (8)0.0035 (8)
C110.0391 (9)0.0550 (11)0.0513 (10)−0.0108 (8)0.0116 (8)−0.0053 (8)
C120.0352 (8)0.0562 (11)0.0507 (10)0.0011 (8)0.0042 (7)−0.0036 (8)
C130.0401 (9)0.0432 (9)0.0422 (9)0.0020 (7)0.0066 (7)−0.0026 (7)
C140.0387 (8)0.0371 (9)0.0386 (8)−0.0022 (7)0.0068 (6)−0.0023 (7)
C150.0445 (9)0.0353 (9)0.0497 (10)−0.0051 (7)0.0036 (7)0.0050 (7)
C160.0417 (9)0.0364 (9)0.0461 (9)−0.0101 (7)0.0036 (7)0.0007 (7)
C170.0486 (11)0.0520 (11)0.0544 (11)0.0057 (9)0.0033 (8)0.0060 (9)
C180.0422 (10)0.0745 (15)0.0786 (15)−0.0188 (10)0.0127 (10)−0.0002 (12)
S10.0460 (3)0.0503 (3)0.0749 (4)−0.0193 (2)−0.0080 (2)0.0180 (2)

Geometric parameters (Å, °)

C1—C21.394 (3)C10—C111.362 (3)
C1—C61.395 (3)C10—H100.9300
C1—S11.7425 (19)C11—C121.411 (3)
C2—C31.368 (3)C11—C181.502 (3)
C2—H20.9300C12—C131.363 (3)
C3—C41.382 (3)C12—H120.9300
C3—H30.9300C13—C141.430 (2)
C4—C51.379 (3)C13—C171.497 (3)
C4—H40.9300C14—C151.406 (2)
C5—C61.386 (3)C15—C161.364 (2)
C5—H50.9300C15—H150.9300
C6—C71.454 (2)C16—S11.7428 (17)
C7—C81.370 (2)C17—H17A0.9600
C7—C161.418 (2)C17—H17B0.9600
C8—C91.410 (2)C17—H17C0.9600
C8—H80.9300C18—H18A0.9600
C9—C101.409 (2)C18—H18B0.9600
C9—C141.425 (2)C18—H18C0.9600
C2—C1—C6121.14 (18)C10—C11—C18122.00 (19)
C2—C1—S1125.84 (16)C12—C11—C18119.55 (19)
C6—C1—S1113.01 (13)C13—C12—C11123.04 (17)
C3—C2—C1118.62 (19)C13—C12—H12118.5
C3—C2—H2120.7C11—C12—H12118.5
C1—C2—H2120.7C12—C13—C14118.76 (16)
C2—C3—C4120.96 (19)C12—C13—C17120.64 (17)
C2—C3—H3119.5C14—C13—C17120.59 (16)
C4—C3—H3119.5C15—C14—C9119.19 (16)
C5—C4—C3120.53 (19)C15—C14—C13121.95 (16)
C5—C4—H4119.7C9—C14—C13118.85 (15)
C3—C4—H4119.7C16—C15—C14119.62 (16)
C4—C5—C6119.81 (19)C16—C15—H15120.2
C4—C5—H5120.1C14—C15—H15120.2
C6—C5—H5120.1C15—C16—C7122.13 (16)
C5—C6—C1118.93 (16)C15—C16—S1125.46 (14)
C5—C6—C7129.09 (17)C7—C16—S1112.39 (13)
C1—C6—C7111.98 (15)C13—C17—H17A109.5
C8—C7—C16118.80 (15)C13—C17—H17B109.5
C8—C7—C6129.86 (16)H17A—C17—H17B109.5
C16—C7—C6111.34 (15)C13—C17—H17C109.5
C7—C8—C9120.82 (16)H17A—C17—H17C109.5
C7—C8—H8119.6H17B—C17—H17C109.5
C9—C8—H8119.6C11—C18—H18A109.5
C10—C9—C8121.39 (16)C11—C18—H18B109.5
C10—C9—C14119.18 (16)H18A—C18—H18B109.5
C8—C9—C14119.43 (15)C11—C18—H18C109.5
C11—C10—C9121.72 (18)H18A—C18—H18C109.5
C11—C10—H10119.1H18B—C18—H18C109.5
C9—C10—H10119.1C1—S1—C1691.28 (9)
C10—C11—C12118.42 (17)
C6—C1—C2—C30.7 (3)C18—C11—C12—C13178.60 (19)
S1—C1—C2—C3179.28 (17)C11—C12—C13—C140.9 (3)
C1—C2—C3—C4−0.1 (3)C11—C12—C13—C17−177.74 (17)
C2—C3—C4—C5−0.2 (4)C10—C9—C14—C15−179.87 (16)
C3—C4—C5—C60.0 (3)C8—C9—C14—C150.4 (3)
C4—C5—C6—C10.6 (3)C10—C9—C14—C131.3 (2)
C4—C5—C6—C7−179.00 (19)C8—C9—C14—C13−178.50 (16)
C2—C1—C6—C5−0.9 (3)C12—C13—C14—C15179.42 (17)
S1—C1—C6—C5−179.67 (14)C17—C13—C14—C15−1.9 (3)
C2—C1—C6—C7178.73 (18)C12—C13—C14—C9−1.7 (3)
S1—C1—C6—C70.0 (2)C17—C13—C14—C9176.94 (16)
C5—C6—C7—C80.2 (3)C9—C14—C15—C16−0.2 (3)
C1—C6—C7—C8−179.43 (18)C13—C14—C15—C16178.66 (17)
C5—C6—C7—C16−179.98 (18)C14—C15—C16—C7−0.3 (3)
C1—C6—C7—C160.4 (2)C14—C15—C16—S1−178.84 (14)
C16—C7—C8—C9−0.3 (3)C8—C7—C16—C150.5 (3)
C6—C7—C8—C9179.59 (17)C6—C7—C16—C15−179.40 (17)
C7—C8—C9—C10−179.90 (16)C8—C7—C16—S1179.24 (13)
C7—C8—C9—C14−0.1 (3)C6—C7—C16—S1−0.65 (19)
C8—C9—C10—C11179.83 (18)C2—C1—S1—C16−179.0 (2)
C14—C9—C10—C110.1 (3)C6—C1—S1—C16−0.29 (15)
C9—C10—C11—C12−0.9 (3)C15—C16—S1—C1179.24 (18)
C9—C10—C11—C18−179.07 (19)C7—C16—S1—C10.54 (14)
C10—C11—C12—C130.4 (3)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C17—H17C···Cg1i0.962.683.486 (2)142
C18—H18A···Cg2ii0.962.753.649 (3)155

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BT2861).

References

  • Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19.
  • Bruker (2004). APEX2 and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Dzhurayev, A. D., Karimkulov, K. M., Makhsumov, A. G. & Amanov, N. (1992). Khim. Farm. Zh.26, 73–75.
  • El-Maghraby, A. A., Haroun, B. & &Mohammed, N. A. (1984). Egypt. J. Pharm. Sci.23, 327–336.
  • Gewald, K., Schinke, E. & Botcher, H. (1996). Chem. Ber.99, 99–100.
  • Harrison, W. T. A., Yathirajan, H. S., Ashalatha, B. V., Vijaya Raj, K. K. & Narayana, B. (2006). Acta Cryst. E62, o3732–o3734.
  • Palani, K., Amaladass, P., Mohanakrishnan, A. K. & Ponnuswamy, M. N. (2006). Acta Cryst. E62, o49–o51.
  • Sheldrick, G. M. (1996). SADABS University of Göttingen, Germany.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Spek, A. L. (2003). J. Appl. Cryst.36, 7–13.

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