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Acta Crystallogr Sect E Struct Rep Online. 2008 July 1; 64(Pt 7): o1263.
Published online 2008 June 13. doi:  10.1107/S1600536808017200
PMCID: PMC2961704

(E)-1-[4-(Methyl­sulfan­yl)phen­yl]-3-phenyl­prop-2-en-1-one

Abstract

In the title mol­ecule, C16H14OS, the dihedral angle between the phenyl and benzene rings is 3.81 (15)°. The H atoms of the central enone group are trans. The propenone unit makes dihedral angles of 11.73 (18) and 11.62 (17)° with the benzene and phenyl rings, respectively. The crystal structure is stabilized by weak C—H(...)O and C—H(...)π inter­actions.

Related literature

For related crystal structures, see Sathiya Moorthi et al. (2005 [triangle]); Moorthi et al. (2005 [triangle]); Thiruvalluvar et al. (2007a [triangle],b [triangle]).

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Object name is e-64-o1263-scheme1.jpg

Experimental

Crystal data

  • C16H14OS
  • M r = 254.34
  • Orthorhombic, An external file that holds a picture, illustration, etc.
Object name is e-64-o1263-efi1.jpg
  • a = 5.6106 (4) Å
  • b = 7.6239 (7) Å
  • c = 30.477 (2) Å
  • V = 1303.64 (17) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.23 mm−1
  • T = 200 (2) K
  • 0.49 × 0.18 × 0.15 mm

Data collection

  • Oxford Diffraction Gemini R diffractometer
  • Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007 [triangle]) T min = 0.849, T max = 1.000 (expected range = 0.820–0.966)
  • 8924 measured reflections
  • 4060 independent reflections
  • 3180 reflections with I > 2σ(I)
  • R int = 0.069

Refinement

  • R[F 2 > 2σ(F 2)] = 0.077
  • wR(F 2) = 0.181
  • S = 1.11
  • 4060 reflections
  • 163 parameters
  • H-atom parameters constrained
  • Δρmax = 0.69 e Å−3
  • Δρmin = −0.38 e Å−3
  • Absolute structure: Flack (1983 [triangle]), 1314 Friedel pairs
  • Flack parameter: 0.11 (16)

Data collection: CrysAlis CCD (Oxford Diffraction, 2007 [triangle]); cell refinement: CrysAlis CCD; data reduction: CrysAlis RED (Oxford Diffraction, 2007 [triangle]); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: ORTEP-3 (Farrugia, 1997 [triangle]); software used to prepare material for publication: PLATON (Spek, 2003 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808017200/wn2267sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808017200/wn2267Isup2.hkl

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

Acknowledgments

RJB acknowledges the NSF–MRI program for funding to purchase the X-ray CCD diffractometer. AT thanks the UGC, India, for the award of a Minor Research Project [File No. MRP-2355/06(UGC-SERO), Link No. 2355, 10/01/2007].

supplementary crystallographic information

Comment

The title compound (Fig. 1) has been analysed as part of our crystallographic studies on chalcones (Thiruvalluvar et al. 2007a,b). The dihedral angle between the phenyl and benzene rings is 3.81 (15)°; the two rings are essentially coplanar. The H atoms of the central enone group are trans. The propenone unit makes dihedral angles of 11.73 (18)° and 11.62 (17)° with the benzene and phenyl rings, respectively.

The crystal structure is stabilized by a weak C3—H3···O1 intramolecular interaction. Furthermore, C12—H12···π, C15—H15···π and C25—H25···π interactions are also found. In similar structures, such as 1-(4-aminophenyl)-3-(3-bromophenyl)-prop-2-en-1-one (Sathiya Moorthi, et al. 2005) and 1-(4-bromophenyl)-3-(3-hydroxy phenyl)prop-2-en-1-one (Moorthi, et al. 2005), the dihedral angles between the two rings are 9.6 (1)° and 10.2 (2)°, respectively.

Experimental

Benzaldehyde (2.12 g, 0.02 mol) in ethanol (22 ml) was mixed with 4'-(methylthio)acetophenone (3.32 g, 0.02 mol) in 40 ml ethanol and the mixture was treated with 10 ml of 10% sodium hydroxide solution at 283 K and stirred at 303–305 K for 8 h. The precipitate obtained was filtered, washed with chilled ethanol and dried. Pale yellow rods of the title compound were grown from toluene by slow evaporation. The yield of the isolated product was 3.4 g (70%).

Refinement

H atoms were positioned geometrically and allowed to ride on their parent atoms, with C—H = 0.95 and 0.98 Å for Csp2 and methyl C, respectively; Uiso(H) = xUeq(C), where x = 1.5 for methyl H and 1.2 for all other H. There was some minor non-merohedral twinning, resulting in Fo2 being consistently larger than Fc2. The 37 most affected reflections were omitted.

Figures

Fig. 1.
The molecular structure of the title compound, showing the atom-numbering scheme and displacement ellipsoids drawn at the 50% probability level. Hydrogen atoms are represented by spheres of arbitrary radius.

Crystal data

C16H14OSDx = 1.296 Mg m3
Mr = 254.34Melting point: 396(1) K
Orthorhombic, P212121Mo Kα radiation λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 3999 reflections
a = 5.6106 (4) Åθ = 4.7–32.4º
b = 7.6239 (7) ŵ = 0.23 mm1
c = 30.477 (2) ÅT = 200 (2) K
V = 1303.64 (17) Å3Needle, colourless
Z = 40.49 × 0.18 × 0.15 mm
F000 = 536

Data collection

Oxford Diffraction Gemini diffractometer4060 independent reflections
Radiation source: fine-focus sealed tube3180 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.069
Detector resolution: 10.5081 pixels mm-1θmax = 32.5º
T = 200(2) Kθmin = 4.7º
[var phi] and ω scansh = −6→8
Absorption correction: multi-scan(CrysAlis RED; Oxford Diffraction, 2007)k = −11→10
Tmin = 0.849, Tmax = 1.000l = −45→38
8924 measured reflections

Refinement

Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.077  w = 1/[σ2(Fo2) + (0.0605P)2 + 1.4543P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.182(Δ/σ)max < 0.001
S = 1.11Δρmax = 0.69 e Å3
4060 reflectionsΔρmin = −0.38 e Å3
163 parametersExtinction correction: none
Primary atom site location: structure-invariant direct methodsAbsolute structure: Flack (1983), 1314 Friedel pairs
Secondary atom site location: difference Fourier mapFlack parameter: 0.11 (16)

Special details

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles
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
S40.48075 (18)0.98501 (13)−0.09063 (3)0.0418 (3)
O10.8645 (4)1.0222 (4)0.11787 (7)0.0411 (8)
C10.6679 (5)0.9800 (4)0.10480 (9)0.0284 (8)
C20.4803 (6)0.9187 (4)0.13565 (9)0.0300 (8)
C30.5318 (6)0.8989 (4)0.17807 (9)0.0273 (8)
C40.7257 (8)1.0997 (6)−0.11513 (11)0.0481 (13)
C110.3725 (6)0.8391 (4)0.21292 (9)0.0269 (8)
C120.4425 (5)0.8603 (4)0.25687 (9)0.0284 (8)
C130.2984 (7)0.8019 (5)0.29078 (10)0.0349 (10)
C140.0835 (7)0.7219 (5)0.28169 (11)0.0374 (10)
C150.0098 (7)0.6998 (4)0.23848 (10)0.0335 (9)
C160.1525 (6)0.7588 (4)0.20435 (10)0.0306 (9)
C210.6093 (5)0.9893 (4)0.05707 (9)0.0239 (7)
C220.7753 (5)1.0701 (4)0.02917 (10)0.0285 (8)
C230.7412 (6)1.0748 (4)−0.01573 (10)0.0296 (8)
C240.5389 (6)0.9955 (4)−0.03416 (9)0.0281 (8)
C250.3704 (5)0.9185 (4)−0.00654 (10)0.0293 (8)
C260.4044 (6)0.9151 (4)0.03850 (10)0.0300 (8)
H20.324420.893740.125180.0360*
H30.690180.926870.186610.0328*
H4A0.707021.09997−0.147100.0720*
H4B0.875271.04105−0.107340.0720*
H4C0.728781.22076−0.104340.0720*
H120.590230.915230.263410.0340*
H130.347670.817040.320360.0419*
H14−0.014520.681750.305040.0449*
H15−0.138080.644310.232330.0402*
H160.100640.744590.174890.0367*
H220.913771.122620.041380.0341*
H230.854421.13149−0.034070.0356*
H250.230770.86768−0.018750.0351*
H260.288020.862250.056870.0360*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
S40.0460 (5)0.0497 (5)0.0297 (3)−0.0035 (5)−0.0048 (3)−0.0008 (3)
O10.0278 (12)0.0601 (17)0.0353 (11)−0.0141 (13)−0.0040 (9)0.0017 (11)
C10.0259 (14)0.0295 (15)0.0297 (12)−0.0040 (13)0.0011 (10)−0.0007 (11)
C20.0243 (14)0.0349 (15)0.0308 (12)−0.0088 (13)0.0007 (11)0.0004 (11)
C30.0215 (14)0.0254 (13)0.0350 (13)−0.0010 (12)0.0022 (11)−0.0006 (11)
C40.051 (2)0.059 (3)0.0342 (16)−0.005 (2)0.0029 (15)0.0084 (17)
C110.0248 (14)0.0252 (14)0.0307 (13)0.0026 (12)0.0026 (11)0.0010 (11)
C120.0218 (15)0.0295 (15)0.0338 (14)0.0040 (11)−0.0026 (11)−0.0009 (11)
C130.0377 (18)0.0378 (18)0.0293 (14)0.0044 (15)0.0003 (13)0.0019 (12)
C140.0379 (19)0.0348 (18)0.0396 (17)0.0129 (14)0.0114 (13)0.0081 (14)
C150.0303 (16)0.0246 (14)0.0456 (16)−0.0027 (14)0.0050 (14)0.0008 (11)
C160.0262 (15)0.0323 (16)0.0332 (14)0.0015 (13)−0.0002 (12)−0.0002 (12)
C210.0210 (12)0.0210 (12)0.0297 (12)0.0003 (11)0.0004 (9)0.0002 (11)
C220.0213 (13)0.0300 (15)0.0341 (14)−0.0069 (12)0.0002 (11)0.0004 (12)
C230.0255 (14)0.0295 (15)0.0339 (14)−0.0023 (12)0.0034 (11)0.0025 (12)
C240.0326 (15)0.0220 (12)0.0297 (12)0.0040 (13)−0.0023 (10)0.0004 (11)
C250.0202 (13)0.0319 (15)0.0357 (14)−0.0070 (12)−0.0032 (11)−0.0034 (12)
C260.0258 (15)0.0316 (15)0.0327 (14)−0.0035 (13)0.0022 (11)0.0001 (12)

Geometric parameters (Å, °)

S4—C41.792 (4)C24—C251.395 (4)
S4—C241.754 (3)C25—C261.386 (4)
O1—C11.216 (4)C2—H20.9500
C1—C21.487 (4)C3—H30.9500
C1—C211.493 (4)C4—H4A0.9800
C2—C31.333 (4)C4—H4B0.9800
C3—C111.461 (4)C4—H4C0.9800
C11—C121.405 (4)C12—H120.9500
C11—C161.402 (5)C13—H130.9500
C12—C131.386 (4)C14—H140.9500
C13—C141.379 (5)C15—H150.9500
C14—C151.391 (5)C16—H160.9500
C15—C161.388 (5)C22—H220.9500
C21—C221.404 (4)C23—H230.9500
C21—C261.401 (4)C25—H250.9500
C22—C231.382 (4)C26—H260.9500
C23—C241.403 (5)
S4···H16i3.1800H2···C262.6800
O1···H2ii2.7700H2···H162.2700
O1···H32.4200H2···H262.1100
O1···H222.4700H3···O12.4200
O1···H4Ciii2.8600H3···C15ii2.9500
O1···H14iv2.7800H3···C16ii2.9400
C3···C13iv3.354 (5)H3···H122.4100
C3···C14iv3.497 (5)H3···C13iv2.9400
C3···C15ii3.590 (5)H3···C14iv2.7600
C12···C15ii3.456 (5)H4A···C14x3.0300
C13···C3v3.354 (5)H4A···H14x2.4600
C14···C3v3.497 (5)H4B···C232.9000
C15···C12vi3.456 (5)H4B···H232.3400
C15···C3vi3.590 (5)H4C···C232.9200
C2···H162.7800H4C···H232.3600
C2···H262.6700H4C···O1ix2.8600
C4···H232.5900H12···C15ii2.9700
C12···H15vii2.7800H12···H32.4100
C12···H15ii2.9700H14···H4Aviii2.4600
C13···H15vii2.8500H14···O1v2.7800
C13···H3v2.9400H15···C12vi2.9700
C14···H3v2.7600H15···C12xi2.7800
C14···H4Aviii3.0300H15···C13xi2.8500
C15···H3vi2.9500H16···C22.7800
C15···H12vi2.9700H16···H22.2700
C16···H22.7900H16···S4xii3.1800
C16···H3vi2.9400H22···O12.4700
C21···H25i3.0400H22···C23iii3.0500
C23···H4B2.9000H22···C24iii3.0000
C23···H4C2.9200H23···C42.5900
C23···H22ix3.0500H23···H4B2.3400
C24···H22ix3.0000H23···H4C2.3600
C25···H25i3.0700H25···C21xii3.0400
C26···H22.6800H25···C25xii3.0700
C26···H25i2.8900H25···C26xii2.8900
H2···O1vi2.7700H26···C22.6700
H2···C162.7900H26···H22.1100
C4—S4—C24104.13 (16)C2—C3—H3116.00
O1—C1—C2121.2 (3)C11—C3—H3116.00
O1—C1—C21120.4 (3)S4—C4—H4A109.00
C2—C1—C21118.4 (2)S4—C4—H4B109.00
C1—C2—C3119.7 (3)S4—C4—H4C109.00
C2—C3—C11127.4 (3)H4A—C4—H4B109.00
C3—C11—C12119.1 (3)H4A—C4—H4C109.00
C3—C11—C16122.6 (3)H4B—C4—H4C109.00
C12—C11—C16118.3 (3)C11—C12—H12120.00
C11—C12—C13120.7 (3)C13—C12—H12120.00
C12—C13—C14120.2 (3)C12—C13—H13120.00
C13—C14—C15120.3 (3)C14—C13—H13120.00
C14—C15—C16119.9 (3)C13—C14—H14120.00
C11—C16—C15120.7 (3)C15—C14—H14120.00
C1—C21—C22117.7 (3)C14—C15—H15120.00
C1—C21—C26123.7 (3)C16—C15—H15120.00
C22—C21—C26118.5 (3)C11—C16—H16120.00
C21—C22—C23121.3 (3)C15—C16—H16120.00
C22—C23—C24119.8 (3)C21—C22—H22119.00
S4—C24—C23124.3 (2)C23—C22—H22119.00
S4—C24—C25116.5 (2)C22—C23—H23120.00
C23—C24—C25119.2 (3)C24—C23—H23120.00
C24—C25—C26120.8 (3)C24—C25—H25120.00
C21—C26—C25120.4 (3)C26—C25—H25120.00
C1—C2—H2120.00C21—C26—H26120.00
C3—C2—H2120.00C25—C26—H26120.00
C4—S4—C24—C23−1.6 (3)C11—C12—C13—C140.0 (5)
C4—S4—C24—C25178.6 (3)C12—C13—C14—C15−0.2 (6)
O1—C1—C2—C3−4.2 (5)C13—C14—C15—C16−0.2 (5)
C21—C1—C2—C3176.0 (3)C14—C15—C16—C110.7 (5)
O1—C1—C21—C22−8.6 (4)C1—C21—C22—C23176.1 (3)
O1—C1—C21—C26168.4 (3)C26—C21—C22—C23−1.0 (5)
C2—C1—C21—C22171.3 (3)C1—C21—C26—C25−175.5 (3)
C2—C1—C21—C26−11.8 (4)C22—C21—C26—C251.4 (5)
C1—C2—C3—C11−179.5 (3)C21—C22—C23—C24−0.9 (5)
C2—C3—C11—C12−167.1 (3)C22—C23—C24—S4−177.5 (2)
C2—C3—C11—C1613.8 (5)C22—C23—C24—C252.4 (5)
C3—C11—C12—C13−178.7 (3)S4—C24—C25—C26177.9 (2)
C16—C11—C12—C130.5 (5)C23—C24—C25—C26−1.9 (5)
C3—C11—C16—C15178.3 (3)C24—C25—C26—C210.0 (5)
C12—C11—C16—C15−0.9 (5)

Symmetry codes: (i) x+1/2, −y+3/2, −z; (ii) x+1, y, z; (iii) x+1/2, −y+5/2, −z; (iv) −x+1, y+1/2, −z+1/2; (v) −x+1, y−1/2, −z+1/2; (vi) x−1, y, z; (vii) −x, y+1/2, −z+1/2; (viii) −x+1/2, −y+2, z+1/2; (ix) x−1/2, −y+5/2, −z; (x) −x+1/2, −y+2, z−1/2; (xi) −x, y−1/2, −z+1/2; (xii) x−1/2, −y+3/2, −z.

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C3—H3···O10.952.422.781 (4)102
C12—H12···Cg1iv0.952.993.704 (3)133
C15—H15···Cg1xi0.952.893.488 (3)122
C25—H25···Cg2xii0.952.903.562 (3)127

Symmetry codes: (iv) −x+1, y+1/2, −z+1/2; (xi) −x, y−1/2, −z+1/2; (xii) x−1/2, −y+3/2, −z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: WN2267).

References

  • Farrugia, L. J. (1997). J. Appl. Cryst.30, 565.
  • Flack, H. D. (1983). Acta Cryst. A39, 876–881.
  • Moorthi, S. S., Chinnakali, K., Nanjundan, S., Unnithan, C. S., Fun, H.-K. & Yu, X.-L. (2005). Acta Cryst. E61, o483–o485.
  • Oxford Diffraction (2007). CrysAlis CCD and CrysAlis RED Oxford Diffraction Ltd, Abingdon, Oxfordshire, England.
  • Sathiya Moorthi, S., Chinnakali, K., Nanjundan, S., Santhi, R. & Fun, H.-K. (2005). Acta Cryst. E61, o3514–o3516.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Spek, A. L. (2003). J. Appl. Cryst.36, 7–13.
  • Thiruvalluvar, A., Subramanyam, M., Butcher, R. J., Adhikari, A. V. & Karabasanagouda, T. (2007b). Acta Cryst. E63, o4716.
  • Thiruvalluvar, A., Subramanyam, M., Butcher, R. J., Adhikari, A. V. & Wagle, S. (2007a). Acta Cryst. E63, o4536.

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