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Acta Crystallogr Sect E Struct Rep Online. 2010 September 1; 66(Pt 9): o2358.
Published online 2010 August 21. doi:  10.1107/S1600536810032769
PMCID: PMC3008090

(2E)-1-(2,5-Dimethyl-3-thien­yl)-3-(2-meth­oxy­phen­yl)prop-2-en-1-one

Abstract

In the title compound, C16H16O2S, the central propenone group is almost planar (r.m.s. deviation = 0.009 Å) and subtends dihedral angles of 8.55 (8) and 16.22 (8)° to the 2-meth­oxy­phenyl and 2,5-dimethyl­thio­phene residues, respectively. The dihedral angle between the ring systems is 23.47 (5)°. In the crystal, mol­ecules are linked by weak C—H(...)π inter­actions and aromatic π–π stacking [phenyl ring centroid–centroid separation = 3.6418 (11) Å; thio­phene–thio­phene ring separation = 3.8727 (9) Å].

Related literature

For background to chalcone derivatives and related crystal structures, see: Asiri et al. (2010a [triangle],b [triangle],c [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-o2358-scheme1.jpg

Experimental

Crystal data

  • C16H16O2S
  • M r = 272.35
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-o2358-efi1.jpg
  • a = 26.2978 (6) Å
  • b = 7.5018 (2) Å
  • c = 14.7242 (3) Å
  • β = 105.771 (1)°
  • V = 2795.45 (11) Å3
  • Z = 8
  • Mo Kα radiation
  • μ = 0.23 mm−1
  • T = 296 K
  • 0.32 × 0.24 × 0.22 mm

Data collection

  • Bruker Kappa APEXII CCD diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2005 [triangle]) T min = 0.937, T max = 0.942
  • 10569 measured reflections
  • 2516 independent reflections
  • 2150 reflections with I > 2σ(I)
  • R int = 0.023

Refinement

  • R[F 2 > 2σ(F 2)] = 0.036
  • wR(F 2) = 0.102
  • S = 1.04
  • 2516 reflections
  • 175 parameters
  • H-atom parameters constrained
  • Δρmax = 0.22 e Å−3
  • Δρmin = −0.21 e Å−3

Data collection: APEX2 (Bruker, 2009 [triangle]); cell refinement: SAINT (Bruker, 2009 [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: ORTEP-3 (Farrugia, 1997 [triangle]) and PLATON (Spek, 2009 [triangle]); software used to prepare material for publication: WinGX (Farrugia, 1999 [triangle]) and PLATON.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810032769/hb5609sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810032769/hb5609Isup2.hkl

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

Acknowledgments

The authors would like to thank the Chemistry Department, King Abdul Aziz University, Jeddah, Saudi Arabia, for providing the research facilities and for the financial support of this work via grant No. (3–045/430).

supplementary crystallographic information

Comment

In continuation of our syntheses of various chalcone derivatives containing the 2,5-dimethylthiophen-3-yl fragment (Asiri et al., 2010a,b,c), the title compound (I, Fig. 1) is now reported.

Recently we have reported the crystal structures of (II) i.e., (E)-1-(2,5-dimethyl-3-thienyl)-3-(2,4,5-trimethoxyphenyl)prop-2-en-1-one (Asiri et al., 2010a), (III) i.e., (2E)-3-(3,4-dimethoxyphenyl)-1-(2,5-dimethylthiophen-3-yl)prop- 2-en-1-one (Asiri et al., 2010b) and (IV) i.e., (E)-1-(2,5-dimethyl-3-thienyl)-3-(2-hydroxyphenyl)prop-2-en-1-one (Asiri et al., 2010c) which contain the common moiety 2,5-dimethylthiophen-3-yl as in (I).

In (I), the group A (C1—C6/O1/C7) of 2-methoxyphenyl, the central propenone B (C8—C10/O2) and group C (C11—C16/S1) of 2,5-dimethylthiophen-3-yl are planar with r. m. s. deviation of 0.0320, 0.0096 and 0.0103 Å, respectively. The dihedral angle between A/B, A/C and B/C is 8.55 (8), 23.47 (5) and 16.22 (8)°, respectively.

In the crystal, the molecules are linked by C—H···π interaction (Table 1), π···π interactions between the centroids of phenyl rings at a distance of 3.6418 (11) Å [symmetry code: - x, - y, 1 - z] and between the centroids of thiophen rings at a distance of 3.8727 (9) Å [symmetry code: 1/2 - x, 1/2 - y, 1 - z].

Experimental

A solution of 3-acetyl-2,5-dimethythiophene (0.38 g, 2.5 mmol) and 2-methoxybenzaldehyde (0.31 g, 2.5 mmol) in ethanolic solution of NaOH (3.0 g in 10 ml of methanol) was stirred for 16 h at room temperature. The solution was poured into ice cold water of pH = 2 (pH adjusted by HCl). The solid was separated and dissolved in CH2Cl2, washed with saturated solution of NaHCO3 and evaporated to dryness. The residual was recrystallized from methanol/chloroform to affoard light yellow prisms of (I).

Yield: 76%; m.p. 364–365 K.

IR (KBr) \vmax cm-1: 2923 (C—H), 1653 (Cδb=O), 1596 (CδbC),

Refinement

The H-atoms were positioned geometrically (C–H = 0.93–0.96 Å) and refined as riding with Uiso(H) = xUeq(C), where x = 1.5 for methyl and x = 1.2 for aryl H-atoms.

Figures

Fig. 1.
View of (I) with displacement ellipsoids drawn at the 50% probability level. H-atoms are shown as small spheres of arbitrary radius.

Crystal data

C16H16O2SF(000) = 1152
Mr = 272.35Dx = 1.294 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 2150 reflections
a = 26.2978 (6) Åθ = 2.8–25.3°
b = 7.5018 (2) ŵ = 0.23 mm1
c = 14.7242 (3) ÅT = 296 K
β = 105.771 (1)°Prism, yellow
V = 2795.45 (11) Å30.32 × 0.24 × 0.22 mm
Z = 8

Data collection

Bruker Kappa APEXII CCD diffractometer2516 independent reflections
Radiation source: fine-focus sealed tube2150 reflections with I > 2σ(I)
graphiteRint = 0.023
Detector resolution: 8.10 pixels mm-1θmax = 25.3°, θmin = 2.8°
ω scansh = −31→31
Absorption correction: multi-scan (SADABS; Bruker, 2005)k = −7→9
Tmin = 0.937, Tmax = 0.942l = −17→17
10569 measured reflections

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)] = 0.036Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.102H-atom parameters constrained
S = 1.04w = 1/[σ2(Fo2) + (0.0538P)2 + 1.6392P] where P = (Fo2 + 2Fc2)/3
2516 reflections(Δ/σ)max < 0.001
175 parametersΔρmax = 0.22 e Å3
0 restraintsΔρmin = −0.21 e Å3

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
S10.32353 (2)−0.13828 (7)0.41788 (3)0.0540 (2)
O10.00471 (4)0.29215 (18)0.37470 (8)0.0503 (4)
O20.15841 (5)0.0916 (2)0.30351 (8)0.0647 (5)
C10.06920 (6)0.1719 (2)0.50255 (10)0.0365 (5)
C20.08539 (6)0.1235 (2)0.59749 (11)0.0440 (5)
C30.05254 (7)0.1426 (3)0.65564 (12)0.0496 (6)
C40.00255 (7)0.2114 (3)0.61901 (12)0.0525 (6)
C5−0.01489 (6)0.2624 (3)0.52590 (12)0.0480 (6)
C60.01817 (6)0.2439 (2)0.46717 (10)0.0380 (5)
C7−0.04837 (7)0.3475 (3)0.33193 (13)0.0534 (6)
C80.10209 (6)0.1431 (2)0.43825 (11)0.0396 (5)
C90.15220 (6)0.0947 (2)0.45997 (11)0.0423 (5)
C100.18032 (6)0.0649 (2)0.38731 (11)0.0401 (5)
C110.23532 (6)−0.0001 (2)0.41814 (10)0.0361 (5)
C120.26768 (6)0.0008 (2)0.51346 (11)0.0405 (5)
C130.31632 (6)−0.0681 (2)0.52502 (12)0.0448 (5)
C140.36036 (7)−0.0865 (3)0.61379 (14)0.0630 (7)
C150.26100 (6)−0.0727 (2)0.35754 (11)0.0420 (5)
C160.24191 (8)−0.1065 (3)0.25341 (12)0.0626 (7)
H20.119140.077260.622190.0528*
H30.063980.109530.718800.0595*
H4−0.019810.223470.657900.0630*
H5−0.048680.309160.502380.0576*
H7A−0.056350.450240.364450.0800*
H7B−0.072180.252510.335650.0800*
H7C−0.052270.377030.266960.0800*
H80.085760.160890.374470.0476*
H90.170340.078870.523110.0507*
H120.256110.045340.563330.0486*
H14A0.35089−0.026900.664540.0945*
H14B0.39191−0.033900.604740.0945*
H14C0.36651−0.210510.628950.0945*
H16A0.233320.004810.220700.0938*
H16B0.21104−0.180810.240320.0938*
H16C0.26916−0.165270.232550.0938*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
S10.0394 (3)0.0688 (3)0.0580 (3)0.0163 (2)0.0204 (2)0.0052 (2)
O10.0342 (6)0.0757 (9)0.0398 (6)0.0147 (6)0.0081 (5)0.0100 (6)
O20.0438 (7)0.1110 (12)0.0373 (7)0.0210 (7)0.0076 (5)0.0071 (7)
C10.0298 (8)0.0410 (9)0.0385 (8)0.0003 (6)0.0091 (6)−0.0011 (6)
C20.0351 (8)0.0551 (10)0.0394 (9)0.0053 (7)0.0061 (7)0.0009 (7)
C30.0500 (10)0.0637 (12)0.0351 (8)0.0017 (9)0.0117 (7)0.0008 (8)
C40.0452 (10)0.0720 (13)0.0459 (10)0.0016 (9)0.0221 (8)−0.0019 (9)
C50.0322 (8)0.0642 (12)0.0488 (10)0.0059 (8)0.0130 (7)−0.0019 (8)
C60.0321 (8)0.0445 (9)0.0367 (8)0.0014 (7)0.0081 (6)0.0000 (7)
C70.0359 (9)0.0684 (12)0.0490 (10)0.0113 (8)−0.0001 (7)0.0044 (8)
C80.0335 (8)0.0471 (9)0.0378 (8)0.0028 (7)0.0088 (6)0.0026 (7)
C90.0323 (8)0.0566 (10)0.0375 (8)0.0064 (7)0.0089 (6)0.0032 (7)
C100.0336 (8)0.0495 (10)0.0364 (8)0.0030 (7)0.0081 (7)0.0018 (7)
C110.0325 (8)0.0409 (9)0.0363 (8)0.0016 (6)0.0116 (6)0.0026 (6)
C120.0330 (8)0.0507 (10)0.0382 (8)0.0014 (7)0.0102 (6)−0.0011 (7)
C130.0352 (9)0.0502 (10)0.0477 (9)0.0018 (7)0.0091 (7)0.0038 (8)
C140.0393 (10)0.0759 (14)0.0635 (12)0.0070 (9)−0.0038 (9)0.0046 (10)
C150.0401 (9)0.0480 (10)0.0405 (8)0.0059 (7)0.0156 (7)0.0056 (7)
C160.0727 (13)0.0774 (14)0.0416 (10)0.0210 (11)0.0224 (9)−0.0023 (9)

Geometric parameters (Å, °)

S1—C131.7217 (17)C13—C141.499 (3)
S1—C151.7150 (17)C15—C161.500 (2)
O1—C61.3595 (18)C2—H20.9300
O1—C71.428 (2)C3—H30.9300
O2—C101.2281 (19)C4—H40.9300
C1—C21.394 (2)C5—H50.9300
C1—C61.409 (2)C7—H7A0.9600
C1—C81.462 (2)C7—H7B0.9600
C2—C31.379 (2)C7—H7C0.9600
C3—C41.378 (3)C8—H80.9300
C4—C51.376 (2)C9—H90.9300
C5—C61.390 (2)C12—H120.9300
C8—C91.320 (2)C14—H14A0.9600
C9—C101.474 (2)C14—H14B0.9600
C10—C111.476 (2)C14—H14C0.9600
C11—C121.430 (2)C16—H16A0.9600
C11—C151.370 (2)C16—H16B0.9600
C12—C131.347 (2)C16—H16C0.9600
C13—S1—C1593.33 (8)C4—C3—H3120.00
C6—O1—C7118.44 (13)C3—C4—H4119.00
C2—C1—C6118.12 (14)C5—C4—H4119.00
C2—C1—C8122.53 (14)C4—C5—H5120.00
C6—C1—C8119.29 (13)C6—C5—H5120.00
C1—C2—C3121.56 (15)O1—C7—H7A109.00
C2—C3—C4119.19 (16)O1—C7—H7B109.00
C3—C4—C5121.20 (17)O1—C7—H7C109.00
C4—C5—C6119.77 (16)H7A—C7—H7B109.00
O1—C6—C1115.79 (13)H7A—C7—H7C109.00
O1—C6—C5124.05 (15)H7B—C7—H7C109.00
C1—C6—C5120.16 (14)C1—C8—H8116.00
C1—C8—C9127.69 (15)C9—C8—H8116.00
C8—C9—C10122.07 (15)C8—C9—H9119.00
O2—C10—C9120.91 (15)C10—C9—H9119.00
O2—C10—C11121.05 (15)C11—C12—H12123.00
C9—C10—C11118.03 (13)C13—C12—H12123.00
C10—C11—C12124.91 (14)C13—C14—H14A109.00
C10—C11—C15123.12 (14)C13—C14—H14B109.00
C12—C11—C15111.96 (14)C13—C14—H14C109.00
C11—C12—C13114.43 (15)H14A—C14—H14B109.00
S1—C13—C12109.81 (13)H14A—C14—H14C109.00
S1—C13—C14121.30 (13)H14B—C14—H14C109.00
C12—C13—C14128.89 (16)C15—C16—H16A109.00
S1—C15—C11110.47 (12)C15—C16—H16B109.00
S1—C15—C16119.25 (13)C15—C16—H16C109.00
C11—C15—C16130.24 (16)H16A—C16—H16B109.00
C1—C2—H2119.00H16A—C16—H16C109.00
C3—C2—H2119.00H16B—C16—H16C109.00
C2—C3—H3120.00
C15—S1—C13—C120.47 (13)C4—C5—C6—O1−179.28 (18)
C15—S1—C13—C14−179.28 (15)C4—C5—C6—C10.5 (3)
C13—S1—C15—C11−0.36 (13)C1—C8—C9—C10178.07 (15)
C13—S1—C15—C16−177.99 (14)C8—C9—C10—O23.1 (2)
C7—O1—C6—C1173.19 (15)C8—C9—C10—C11−176.16 (15)
C7—O1—C6—C5−7.0 (2)O2—C10—C11—C12166.02 (16)
C6—C1—C2—C30.9 (2)O2—C10—C11—C15−15.4 (2)
C8—C1—C2—C3−176.26 (16)C9—C10—C11—C12−14.7 (2)
C2—C1—C6—O1178.75 (14)C9—C10—C11—C15163.82 (15)
C2—C1—C6—C5−1.1 (2)C10—C11—C12—C13178.89 (14)
C8—C1—C6—O1−4.0 (2)C15—C11—C12—C130.2 (2)
C8—C1—C6—C5176.16 (16)C10—C11—C15—S1−178.56 (12)
C2—C1—C8—C9−10.4 (3)C10—C11—C15—C16−1.3 (3)
C6—C1—C8—C9172.51 (16)C12—C11—C15—S10.16 (17)
C1—C2—C3—C4−0.1 (3)C12—C11—C15—C16177.45 (17)
C2—C3—C4—C5−0.5 (3)C11—C12—C13—S1−0.46 (18)
C3—C4—C5—C60.3 (3)C11—C12—C13—C14179.26 (17)

Hydrogen-bond geometry (Å, °)

Cg2 is the centroid of C1–C6 ring.
D—H···AD—HH···AD···AD—H···A
C7—H7A···Cg2i0.962.893.768 (2)153

Symmetry codes: (i) −x, −y+1, −z+1.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB5609).

References

  • Asiri, A. M., Khan, S. A. & Tahir, M. N. (2010a). Acta Cryst. E66, o2099. [PMC free article] [PubMed]
  • Asiri, A. M., Khan, S. A. & Tahir, M. N. (2010b). Acta Cryst. E66, o2133. [PMC free article] [PubMed]
  • Asiri, A. M., Khan, S. A. & Tahir, M. N. (2010c). Acta Cryst. E66, o2259–o2260. [PMC free article] [PubMed]
  • Bruker (2005). SADABS Bruker AXS Inc., Madison, Wisconsin, USA.
  • Bruker (2009). APEX2 and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Farrugia, L. J. (1997). J. Appl. Cryst.30, 565.
  • Farrugia, L. J. (1999). J. Appl. Cryst.32, 837–838.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Spek, A. L. (2009). Acta Cryst. D65, 148–155. [PMC free article] [PubMed]

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