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Acta Crystallogr Sect E Struct Rep Online. 2010 June 1; 66(Pt 6): o1449.
Published online 2010 May 26. doi:  10.1107/S1600536810018866
PMCID: PMC2979385

3-(4-Methoxy­benz­yl)-1-benzothio­phene

Abstract

In the title compound, C16H14OS, the dihedral angle between the benzothio­phene ring system and the benzene ring is 72.41 (12)°. A weak inter­molecular C—H(...)π inter­action from the benzene ring to the benzothio­phene ring system is observed in the crystal structure.

Related literature

For the biological activity of thio­phene derivatives, see: Bonini et al. (2005 [triangle]); Brault et al. (2005 [triangle]); Isloora et al. (2010 [triangle]). For related structures, see: Gunasekaran et al. (2009 [triangle]); Umadevi et al. (2009 [triangle]). For bond-length data, see: Allen et al. (1987 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-o1449-scheme1.jpg

Experimental

Crystal data

  • C16H14OS
  • M r = 254.33
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-o1449-efi1.jpg
  • a = 8.0158 (6) Å
  • b = 10.8230 (9) Å
  • c = 8.1219 (6) Å
  • β = 112.563 (4)°
  • V = 650.68 (9) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 0.23 mm−1
  • T = 295 K
  • 0.25 × 0.20 × 0.20 mm

Data collection

  • Bruker SMART APEXII CCD diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.946, T max = 0.954
  • 6033 measured reflections
  • 2946 independent reflections
  • 2721 reflections with I > 2σ(I)
  • R int = 0.171

Refinement

  • R[F 2 > 2σ(F 2)] = 0.066
  • wR(F 2) = 0.176
  • S = 1.06
  • 2946 reflections
  • 164 parameters
  • 2 restraints
  • H-atom parameters constrained
  • Δρmax = 0.35 e Å−3
  • Δρmin = −0.48 e Å−3
  • Absolute structure: Flack (1983 [triangle]), 1337 Friedel pairs
  • Flack parameter: −0.04 (11)

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, 2009 [triangle]); software used to prepare material for publication: SHELXL97.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810018866/is2551sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810018866/is2551Isup2.hkl

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

Acknowledgments

BG thanks AMET University management, India, for their kind support.

supplementary crystallographic information

Comment

Thiophene derivatives exhibit anti-HIV PR inhibitors (Bonini et al., 2005) and anti-breast cancer (Brault et al., 2005) activities. In addition, some of the benzo[b]thiophene derivatives shows significant antimicrobial and anti-inflammatory activities (Isloora et al., 2010).

The geometric parameters of the title molecule (Fig. 1) agree well with reported similar structures (Gunasekaran et al., 2009; Umadevi et al., 2009). The dihedral angle between the two benzene rings is 71.93 (8)°. The C1—S1 and C8—S1 bond distances are 1.738 (3) and 1.734 (3) Å respectively, which are comparable to the literature value of 1.712 (2) Å (Allen et al., 1987).

The crystal packing is stabilized by a weak C—H···π interaction [C14—H14···Cg (-1+x, y, -1+z), Table 1; Cg is the centroid of the ring defined by the atoms C1—C6] .

Experimental

To a solution of 1-(bromomethyl)-4-methoxybenzene (0.7 g, 3.48 mmol) in dry 1,2-dichloroethane (20 ml) ZnBr2 (0.23 g, 1.02 mmol) and benzo[b]thiophene (0.7 g, 5.22 mmol) were added. It was then stirred at room temperature for 6 h under N2 atmosphere. The solvent was removed and the residue was quenched with ice-water (50 ml) containing 1 ml of conc. HCl, extracted with chloroform (2 × 10 ml) and dried (Na2SO4). Removal of solvent followed by column chromatographic purification (n-hexane/ethyl acetate 94:6) afforded the product as a colourless crystal.

Refinement

H atoms were positioned geometrically and refined using riding model with C—H = 0.93 Å and Uiso(H) = 1.2Ueq(C) for aromatic C—H, C—H = 0.97 Å and Uiso(H) = 1.2Ueq(C) for CH2, C—H = 0.96 Å and Uiso(H) = 1.5Ueq(C) for CH3.

Figures

Fig. 1.
The molecular structure of (I), with atom labels and 30% probability displacement ellipsoids for non-H atoms.

Crystal data

C16H14OSF(000) = 268
Mr = 254.33Dx = 1.298 Mg m3
Monoclinic, PcMo Kα radiation, λ = 0.71073 Å
Hall symbol: P -2ycCell parameters from 4241 reflections
a = 8.0158 (6) Åθ = 2.7–28.3°
b = 10.8230 (9) ŵ = 0.23 mm1
c = 8.1219 (6) ÅT = 295 K
β = 112.563 (4)°Block, colourless
V = 650.68 (9) Å30.25 × 0.20 × 0.20 mm
Z = 2

Data collection

Bruker SMART APEXII CCD diffractometer2946 independent reflections
Radiation source: fine-focus sealed tube2721 reflections with I > 2σ(I)
graphiteRint = 0.171
Detector resolution: 0 pixels mm-1θmax = 28.3°, θmin = 1.9°
ω and [var phi] scansh = −10→9
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)k = −12→14
Tmin = 0.946, Tmax = 0.954l = −10→10
6033 measured reflections

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.066H-atom parameters constrained
wR(F2) = 0.176w = 1/[σ2(Fo2) + (0.1211P)2 + 0.025P] where P = (Fo2 + 2Fc2)/3
S = 1.06(Δ/σ)max < 0.001
2946 reflectionsΔρmax = 0.35 e Å3
164 parametersΔρmin = −0.48 e Å3
2 restraintsAbsolute structure: Flack (1983), 1337 Friedel pairs
Primary atom site location: structure-invariant direct methodsFlack parameter: −0.04 (11)

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

xyzUiso*/Ueq
C10.9043 (4)0.0721 (3)0.6766 (3)0.0493 (6)
C21.0778 (5)0.0242 (3)0.7621 (4)0.0607 (7)
H21.0969−0.05100.82190.073*
C31.2203 (5)0.0925 (4)0.7547 (5)0.0671 (9)
H31.33740.06270.81110.081*
C41.1926 (5)0.2048 (4)0.6648 (5)0.0616 (7)
H41.29120.24940.66340.074*
C51.0204 (4)0.2504 (3)0.5777 (4)0.0513 (6)
H51.00250.32500.51650.062*
C60.8728 (3)0.1837 (2)0.5821 (3)0.0423 (5)
C70.6844 (3)0.2155 (2)0.5029 (3)0.0433 (5)
C80.5818 (4)0.1302 (3)0.5405 (4)0.0488 (5)
H80.45680.13620.50040.059*
C90.6202 (4)0.3311 (3)0.3944 (4)0.0557 (6)
H9A0.66620.33150.30000.067*
H9B0.67160.40180.47030.067*
C100.4183 (4)0.3466 (3)0.3119 (3)0.0497 (6)
C110.3305 (4)0.4346 (3)0.3745 (4)0.0532 (6)
H110.39750.48440.47040.064*
C120.1454 (4)0.4492 (3)0.2967 (4)0.0542 (6)
H120.08990.51010.33870.065*
C130.0417 (4)0.3743 (3)0.1570 (3)0.0470 (6)
C140.1274 (4)0.2862 (3)0.0923 (3)0.0517 (6)
H140.06050.2357−0.00280.062*
C150.3130 (4)0.2744 (3)0.1708 (4)0.0563 (7)
H150.36900.21530.12650.068*
C16−0.2496 (5)0.3249 (5)−0.0572 (6)0.0793 (11)
H16A−0.22530.3485−0.15970.119*
H16B−0.37460.3397−0.07990.119*
H16C−0.22330.2386−0.03320.119*
O1−0.1408 (3)0.3948 (3)0.0910 (3)0.0653 (6)
S10.70297 (12)0.00836 (7)0.67020 (11)0.0601 (2)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
C10.0614 (14)0.0440 (15)0.0452 (11)−0.0010 (11)0.0235 (10)−0.0009 (10)
C20.0703 (18)0.0529 (17)0.0552 (15)0.0134 (14)0.0201 (12)0.0062 (12)
C30.0586 (16)0.074 (2)0.0644 (16)0.0158 (15)0.0191 (13)−0.0042 (15)
C40.0546 (14)0.0643 (18)0.0702 (15)−0.0037 (14)0.0286 (12)−0.0104 (16)
C50.0569 (14)0.0447 (14)0.0579 (13)−0.0035 (11)0.0283 (11)−0.0016 (10)
C60.0517 (12)0.0365 (12)0.0417 (9)−0.0009 (9)0.0213 (9)−0.0032 (8)
C70.0511 (11)0.0377 (12)0.0430 (10)−0.0007 (10)0.0203 (8)−0.0007 (9)
C80.0549 (13)0.0414 (13)0.0537 (11)−0.0035 (11)0.0250 (10)−0.0008 (10)
C90.0563 (14)0.0430 (15)0.0645 (14)0.0016 (12)0.0196 (11)0.0102 (12)
C100.0580 (14)0.0403 (13)0.0511 (12)0.0057 (11)0.0211 (10)0.0068 (10)
C110.0699 (16)0.0396 (14)0.0490 (11)−0.0006 (12)0.0218 (11)−0.0037 (10)
C120.0717 (17)0.0425 (14)0.0544 (12)0.0106 (12)0.0309 (12)−0.0033 (11)
C130.0583 (14)0.0412 (13)0.0447 (10)0.0112 (10)0.0233 (10)0.0049 (9)
C140.0597 (14)0.0473 (15)0.0442 (10)0.0103 (12)0.0155 (10)−0.0068 (10)
C150.0633 (16)0.0526 (17)0.0528 (12)0.0161 (12)0.0221 (11)−0.0033 (11)
C160.0594 (19)0.078 (3)0.090 (2)0.0062 (16)0.0179 (17)−0.014 (2)
O10.0607 (12)0.0675 (16)0.0672 (12)0.0173 (11)0.0238 (9)−0.0048 (11)
S10.0723 (4)0.0462 (4)0.0659 (4)−0.0059 (3)0.0312 (3)0.0108 (3)

Geometric parameters (Å, °)

C1—C21.394 (5)C9—H9A0.9700
C1—C61.401 (4)C9—H9B0.9700
C1—S11.738 (3)C10—C151.376 (4)
C2—C31.381 (6)C10—C111.392 (4)
C2—H20.9300C11—C121.380 (4)
C3—C41.391 (6)C11—H110.9300
C3—H30.9300C12—C131.383 (4)
C4—C51.379 (5)C12—H120.9300
C4—H40.9300C13—O11.369 (4)
C5—C61.398 (4)C13—C141.391 (4)
C5—H50.9300C14—C151.381 (4)
C6—C71.438 (4)C14—H140.9300
C7—C81.347 (4)C15—H150.9300
C7—C91.503 (4)C16—O11.406 (5)
C8—S11.734 (3)C16—H16A0.9600
C8—H80.9300C16—H16B0.9600
C9—C101.504 (4)C16—H16C0.9600
C2—C1—C6121.9 (3)C10—C9—H9B108.5
C2—C1—S1127.2 (3)H9A—C9—H9B107.5
C6—C1—S1110.9 (2)C15—C10—C11117.3 (3)
C3—C2—C1117.6 (3)C15—C10—C9121.3 (3)
C3—C2—H2121.2C11—C10—C9121.5 (3)
C1—C2—H2121.2C12—C11—C10121.1 (3)
C2—C3—C4121.5 (3)C12—C11—H11119.4
C2—C3—H3119.2C10—C11—H11119.4
C4—C3—H3119.2C11—C12—C13120.7 (2)
C5—C4—C3120.6 (3)C11—C12—H12119.6
C5—C4—H4119.7C13—C12—H12119.6
C3—C4—H4119.7O1—C13—C12116.2 (2)
C4—C5—C6119.5 (3)O1—C13—C14124.9 (3)
C4—C5—H5120.2C12—C13—C14118.9 (3)
C6—C5—H5120.2C15—C14—C13119.3 (3)
C5—C6—C1118.9 (3)C15—C14—H14120.3
C5—C6—C7128.2 (2)C13—C14—H14120.3
C1—C6—C7112.9 (2)C10—C15—C14122.7 (3)
C8—C7—C6111.2 (2)C10—C15—H15118.7
C8—C7—C9127.0 (3)C14—C15—H15118.7
C6—C7—C9121.8 (2)O1—C16—H16A109.5
C7—C8—S1114.3 (2)O1—C16—H16B109.5
C7—C8—H8122.9H16A—C16—H16B109.5
S1—C8—H8122.9O1—C16—H16C109.5
C7—C9—C10114.9 (2)H16A—C16—H16C109.5
C7—C9—H9A108.5H16B—C16—H16C109.5
C10—C9—H9A108.5C13—O1—C16117.8 (3)
C7—C9—H9B108.5C8—S1—C190.76 (14)
C6—C1—C2—C31.6 (4)C6—C7—C9—C10176.5 (2)
S1—C1—C2—C3−178.0 (2)C7—C9—C10—C15−71.9 (4)
C1—C2—C3—C4−0.3 (5)C7—C9—C10—C11108.3 (3)
C2—C3—C4—C5−0.9 (5)C15—C10—C11—C12−0.6 (4)
C3—C4—C5—C60.8 (5)C9—C10—C11—C12179.2 (3)
C4—C5—C6—C10.5 (4)C10—C11—C12—C131.7 (4)
C4—C5—C6—C7179.1 (3)C11—C12—C13—O1179.0 (3)
C2—C1—C6—C5−1.7 (4)C11—C12—C13—C14−1.9 (4)
S1—C1—C6—C5177.95 (19)O1—C13—C14—C15−179.9 (3)
C2—C1—C6—C7179.4 (3)C12—C13—C14—C151.1 (4)
S1—C1—C6—C7−0.9 (3)C11—C10—C15—C14−0.3 (5)
C5—C6—C7—C8−178.0 (3)C9—C10—C15—C14179.9 (3)
C1—C6—C7—C80.8 (3)C13—C14—C15—C100.0 (5)
C5—C6—C7—C91.7 (4)C12—C13—O1—C16176.7 (3)
C1—C6—C7—C9−179.6 (2)C14—C13—O1—C16−2.4 (5)
C6—C7—C8—S1−0.3 (3)C7—C8—S1—C1−0.2 (2)
C9—C7—C8—S1−179.9 (2)C2—C1—S1—C8−179.7 (3)
C8—C7—C9—C10−3.9 (4)C6—C1—S1—C80.6 (2)

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C1–C6 ring.
D—H···AD—HH···AD···AD—H···A
C14—H14···Cgi0.932.833.617 (2)143

Symmetry codes: (i) x−1, y, z−1.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: IS2551).

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.
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