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Acta Crystallogr Sect E Struct Rep Online. 2010 June 1; 66(Pt 6): o1385.
Published online 2010 May 19. doi:  10.1107/S1600536810017058
PMCID: PMC2979389

1-(2-Hydr­oxy-5-methyl­phen­yl)-3-(3-methylthiophen-2-yl)prop-2-en-1-one

Abstract

In the structure of the title compound, C15H14O2S, the benzene ring is nearly coplanar with the thio­phene ring. The hydroxy group substituted at C2 position is in an antiperi­planar conformation with respect to the phenyl ring. The crystal structure exhibits weak intramolecular O—H(...)O hydrogen bonding.

Related literature

For the bioactivity of related compounds, see: Ratty (1988 [triangle]); Sato et al. (1996 [triangle]); Tencate et al. (1973 [triangle]); Murakami et al. (1992 [triangle]); Gerdin & Srensso (1983 [triangle]); Shahidi et al.(1988 [triangle]); Jayashree et al. (2008 [triangle]); Nijveldt et al. (2001 [triangle]); Varma & Kinoshita (1976 [triangle]). For related structures, see: Jasinski et al. (2009 [triangle], 2010 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-o1385-scheme1.jpg

Experimental

Crystal data

  • C15H14O2S
  • M r = 258.33
  • Orthorhombic, An external file that holds a picture, illustration, etc.
Object name is e-66-o1385-efi1.jpg
  • a = 13.6680 (12) Å
  • b = 13.3750 (8) Å
  • c = 14.5410 (14) Å
  • V = 2658.2 (4) Å3
  • Z = 8
  • Mo Kα radiation
  • μ = 0.23 mm−1
  • T = 293 K
  • 0.27 × 0.25 × 0.23 mm

Data collection

  • MacScience DIPLabo 32001 diffractometer
  • 4360 measured reflections
  • 2335 independent reflections
  • 1742 reflections with I > 2σ(I)
  • R int = 0.016

Refinement

  • R[F 2 > 2σ(F 2)] = 0.058
  • wR(F 2) = 0.182
  • S = 1.07
  • 2335 reflections
  • 166 parameters
  • H-atom parameters constrained
  • Δρmax = 0.24 e Å−3
  • Δρmin = −0.35 e Å−3

Data collection: XPRESS (MacScience, 2002 [triangle]); cell refinement: SCALEPACK (Otwinowski & Minor, 1997 [triangle]); data reduction: DENZO (Otwinowski & Minor, 1997 [triangle]) and SCALEPACK; 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]) and ORTEPII (Johnson, 1976 [triangle]); software used to prepare material for publication: PLATON.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810017058/jh2143sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810017058/jh2143Isup2.hkl

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

Acknowledgments

The authors are grateful to the Department of Science and Technology and the Government of India (project SP/I2/FOO/93) and the University of Mysore for financial assistance. The authors duly acknowledge Manipal College of Pharmaceutical Sciences for providing facilities to carry out the synthetic work.

supplementary crystallographic information

Comment

Chalcone is the basic skeleton present in all flavonoids, which are important secondary plant metabolities reported to exhibit a wide range of biological activities such as anti-oxidant (Ratty, 1988), anti-bacterial (Sato et al., 1996), anti-fungal (Tencate et al., 1973), anti-cancer (Murakami et al., 1992), anti-HIV (Gerdin et al., 1983), anti-inflammatory (Shahidi et al., 1988) and inhibition of various enzymens such as aldose reductase, cycloxigenase, tyrosinkinase (Varma et al., 1976). The hydroxy group has exhibited a broad range of biological activities displaying anti-oxidant, anti-bacterials, anti-diabetic properties (Jayashree et al., 2008). The unsaturated ketone group present in chalcones is believed to be responsible for the biological activity (Nijveldt et al., 2001). In view of the importance of such compounds the title compound is synthesised and its crystal structure is reported.

The molecular structure of 1-(2-hydroxy-5-methylphenyl)-3-(3-methylthiophen-2-yl)prop-2-en-1-one, consists of a phenyl ring and a thiophen ring attached to a propanone chain at 1,3-position. The bond lengths C7–C9, C9–O10, C9–C11, C11–C12, C12–C13 and bond angles C7–C9–O10, O10–C9–C11 are in good agreement with those of the similar compounds reported earlier (Jasinski et al., 2009; Jasinski et al., 2010). The torsion angle for C12-C13-C17-C18 is -1.71° and adopts -syn-periplanar conformation. The structure exhibits weak intramolecular hydrogen bond of the type O–H···O.

Experimental

The title compound 1-(2-hydroxy-5-methylphenyl)-3-(3-methylthiophen-2-yl)prop-2-en-1-one was synthesized by dissolving 5 m mole of 5-methyl-2 hydroxyacetophenone in 15 ml of methanol taken in a conical flask, towhich 5 ml of aqueous solution of sodium hydroxide was added with stirring at room temperature. Later 5 m mole of 5-methyl-2-thiophene-carboxaldehyde was added slowly and the stirring continued for 48 hours. The mixture was then poured into ice cold water and acidified with dilute hydrochloric acid. The title compound separates as a precipitate which was collected by filtration, dried and recrystallised from methanol.

Figures

Fig. 1.
Crystal structure of the title compound with 50% probability displacement ellipsoids.

Crystal data

C15H14O2SF(000) = 1088
Mr = 258.33Dx = 1.291 Mg m3
Orthorhombic, PbcaMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2abCell parameters from 4360 reflections
a = 13.6680 (12) Åθ = 3.2–25.0°
b = 13.3750 (8) ŵ = 0.23 mm1
c = 14.5410 (14) ÅT = 293 K
V = 2658.2 (4) Å3Rectangular, orange
Z = 80.27 × 0.25 × 0.23 mm

Data collection

MacScience DIPLabo 32001 diffractometer1742 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.016
graphiteθmax = 25.0°, θmin = 3.2°
Detector resolution: 10.0 pixels mm-1h = −15→16
ω scansk = −15→15
4360 measured reflectionsl = −17→17
2335 independent 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)] = 0.058H-atom parameters constrained
wR(F2) = 0.182w = 1/[σ2(Fo2) + (0.1131P)2 + 0.2932P] where P = (Fo2 + 2Fc2)/3
S = 1.07(Δ/σ)max < 0.001
2335 reflectionsΔρmax = 0.24 e Å3
166 parametersΔρmin = −0.35 e Å3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.009975

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
S140.03308 (6)0.63213 (6)0.34076 (5)0.0917 (3)
O1−0.30633 (16)0.21283 (14)0.47357 (17)0.1086 (9)
O10−0.14602 (14)0.28250 (13)0.41732 (14)0.0902 (7)
C2−0.32536 (19)0.3053 (2)0.5061 (2)0.0824 (9)
C3−0.4133 (2)0.3227 (3)0.5511 (2)0.0998 (11)
C4−0.4358 (2)0.4136 (3)0.5850 (2)0.0968 (13)
C5−0.37207 (18)0.4947 (2)0.57621 (16)0.0817 (9)
C6−0.28521 (17)0.47858 (19)0.53026 (16)0.0714 (8)
C7−0.25907 (16)0.38552 (17)0.49421 (16)0.0681 (8)
C8−0.3971 (2)0.5955 (3)0.6154 (2)0.1067 (14)
C9−0.16789 (18)0.36901 (17)0.44277 (16)0.0692 (8)
C11−0.10438 (16)0.45228 (18)0.41721 (15)0.0685 (8)
C12−0.02561 (16)0.43481 (19)0.36459 (17)0.0702 (8)
C130.04379 (16)0.5047 (2)0.32810 (16)0.0724 (8)
C150.1358 (3)0.6508 (3)0.2772 (2)0.1040 (12)
C160.1769 (2)0.5658 (3)0.2486 (2)0.0996 (13)
C170.12548 (19)0.4798 (2)0.27636 (17)0.0830 (9)
C180.1554 (2)0.3751 (3)0.2526 (2)0.1080 (14)
H1−0.253100.212800.447500.1630*
H3−0.457600.270500.558000.1200*
H4−0.495200.422600.615000.1160*
H6−0.242200.531900.523000.0860*
H8A−0.356800.645600.587200.1600*
H8B−0.385900.595100.680600.1600*
H8C−0.464700.610100.603500.1600*
H11−0.118400.516800.437200.0820*
H12−0.014500.368100.349700.0840*
H150.160800.713800.263800.1250*
H160.233800.563600.213600.1200*
H18A0.149800.333400.306100.1620*
H18B0.222000.375000.231600.1620*
H18C0.113700.349800.204900.1620*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
S140.1046 (6)0.0844 (6)0.0861 (6)−0.0070 (3)0.0065 (4)0.0020 (3)
O10.0995 (14)0.0704 (12)0.156 (2)−0.0136 (9)−0.0070 (13)0.0142 (12)
O100.0902 (12)0.0694 (11)0.1110 (14)0.0007 (9)0.0016 (10)−0.0092 (9)
C20.0757 (14)0.0763 (16)0.0953 (18)−0.0082 (12)−0.0099 (13)0.0177 (14)
C30.0765 (17)0.104 (2)0.119 (2)−0.0175 (16)−0.0017 (16)0.0356 (19)
C40.0715 (16)0.125 (3)0.094 (2)−0.0003 (16)0.0098 (14)0.0259 (19)
C50.0724 (14)0.106 (2)0.0666 (14)0.0062 (13)0.0035 (11)0.0083 (13)
C60.0704 (13)0.0763 (15)0.0676 (13)−0.0012 (11)−0.0008 (10)0.0029 (11)
C70.0659 (13)0.0703 (14)0.0681 (13)−0.0029 (10)−0.0056 (10)0.0109 (11)
C80.103 (2)0.124 (3)0.093 (2)0.0186 (18)0.0217 (17)−0.0114 (19)
C90.0698 (13)0.0652 (14)0.0725 (14)0.0004 (10)−0.0066 (11)0.0009 (11)
C110.0684 (13)0.0682 (14)0.0688 (13)−0.0007 (10)0.0007 (10)−0.0006 (11)
C120.0714 (14)0.0743 (15)0.0650 (13)0.0034 (10)−0.0034 (11)0.0013 (11)
C130.0704 (13)0.0843 (17)0.0624 (13)0.0039 (11)−0.0001 (10)0.0043 (11)
C150.110 (2)0.112 (2)0.090 (2)−0.0278 (19)0.0034 (17)0.0192 (18)
C160.0887 (19)0.130 (3)0.0801 (17)−0.0134 (18)0.0133 (14)0.0117 (17)
C170.0744 (14)0.106 (2)0.0685 (14)0.0040 (13)0.0009 (11)0.0094 (14)
C180.093 (2)0.125 (3)0.106 (2)0.0234 (18)0.0195 (18)0.0011 (19)

Geometric parameters (Å, °)

S14—C131.721 (3)C15—C161.335 (5)
S14—C151.699 (4)C16—C171.407 (5)
O1—C21.350 (3)C17—C181.499 (5)
O10—C91.251 (3)C3—H30.9300
O1—H10.8200C4—H40.9300
C2—C71.415 (3)C6—H60.9300
C2—C31.388 (4)C8—H8A0.9600
C3—C41.348 (5)C8—H8B0.9600
C4—C51.397 (4)C8—H8C0.9600
C5—C61.379 (3)C11—H110.9300
C5—C81.503 (5)C12—H120.9300
C6—C71.397 (3)C15—H150.9300
C7—C91.470 (3)C16—H160.9300
C9—C111.460 (3)C18—H18A0.9600
C11—C121.341 (3)C18—H18B0.9600
C12—C131.434 (3)C18—H18C0.9600
C13—C171.387 (3)
C13—S14—C1590.98 (16)C2—C3—H3119.00
C2—O1—H1109.00C4—C3—H3119.00
O1—C2—C7121.9 (2)C3—C4—H4119.00
C3—C2—C7119.0 (3)C5—C4—H4119.00
O1—C2—C3119.1 (3)C5—C6—H6119.00
C2—C3—C4121.4 (3)C7—C6—H6119.00
C3—C4—C5121.7 (3)C5—C8—H8A109.00
C4—C5—C6117.4 (3)C5—C8—H8B109.00
C4—C5—C8121.3 (2)C5—C8—H8C109.00
C6—C5—C8121.3 (2)H8A—C8—H8B110.00
C5—C6—C7122.8 (2)H8A—C8—H8C109.00
C2—C7—C6117.8 (2)H8B—C8—H8C109.00
C6—C7—C9122.8 (2)C9—C11—H11120.00
C2—C7—C9119.4 (2)C12—C11—H11120.00
O10—C9—C11119.2 (2)C11—C12—H12116.00
C7—C9—C11121.3 (2)C13—C12—H12116.00
O10—C9—C7119.5 (2)S14—C15—H15123.00
C9—C11—C12119.3 (2)C16—C15—H15124.00
C11—C12—C13129.0 (2)C15—C16—H16123.00
S14—C13—C12123.37 (18)C17—C16—H16123.00
C12—C13—C17125.2 (2)C17—C18—H18A110.00
S14—C13—C17111.37 (19)C17—C18—H18B109.00
S14—C15—C16113.1 (3)C17—C18—H18C110.00
C15—C16—C17113.4 (3)H18A—C18—H18B109.00
C13—C17—C18124.7 (2)H18A—C18—H18C109.00
C16—C17—C18124.1 (2)H18B—C18—H18C109.00
C13—C17—C16111.2 (2)
C15—S14—C13—C12−177.8 (2)C2—C7—C9—C11170.9 (2)
C15—S14—C13—C170.4 (2)C6—C7—C9—C11−7.2 (4)
C13—S14—C15—C16−0.7 (3)C2—C7—C9—O10−6.3 (4)
O1—C2—C7—C6180.0 (2)C6—C7—C9—O10175.6 (2)
C3—C2—C7—C61.1 (4)O10—C9—C11—C122.1 (3)
C3—C2—C7—C9−177.1 (2)C7—C9—C11—C12−175.2 (2)
O1—C2—C7—C91.8 (4)C9—C11—C12—C13177.0 (2)
O1—C2—C3—C4179.9 (3)C11—C12—C13—S14−4.3 (4)
C7—C2—C3—C4−1.3 (4)C11—C12—C13—C17177.8 (2)
C2—C3—C4—C50.3 (5)S14—C13—C17—C160.0 (3)
C3—C4—C5—C8−179.1 (3)C12—C13—C17—C16178.1 (2)
C3—C4—C5—C60.8 (4)C12—C13—C17—C18−1.7 (4)
C8—C5—C6—C7179.0 (2)S14—C13—C17—C18−179.8 (2)
C4—C5—C6—C7−0.9 (4)S14—C15—C16—C170.8 (4)
C5—C6—C7—C2−0.1 (4)C15—C16—C17—C13−0.5 (4)
C5—C6—C7—C9178.1 (2)C15—C16—C17—C18179.4 (3)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O1—H1···O100.821.792.518 (3)147

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: JH2143).

References

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