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Acta Crystallogr Sect E Struct Rep Online. 2010 July 1; 66(Pt 7): o1717.
Published online 2010 June 18. doi:  10.1107/S1600536810022725
PMCID: PMC3006779

(2E)-1-(2,5-Dichloro-3-thien­yl)-3-(6-meth­oxy-2-naphth­yl)prop-2-en-1-one

Abstract

In the title compound, C18H12Cl2O2S, the dihedral angle between the thio­phene ring and the naphthalene ring system is 2.13 (4)°. In the crystal, pairs of weak inter­molecular C—H(...)O hydrogen bonds form centrosymmetric dimers.

Related literature

For the biological activity of thio­phene-containing compounds, see: Ferreira et al. (2006 [triangle]); Bonini et al. (2005 [triangle]); Kulikova et al. (1980 [triangle]). For the anti­radiation activity of thio­phenes, see: Hassan et al. (1998 [triangle]). For the synthesis and anti­microbial evaluation of new chalcones, see: Tomar et al. (2007 [triangle]). For the biological activity of chalcone derivatives, see: Nowakowska et al. (2007 [triangle]). For related structures, see: Butcher et al. (2007 [triangle]); Harrison et al. (2007a [triangle],b [triangle]); Li et al. (2009 [triangle]); Yathirajan et al. (2006 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-o1717-scheme1.jpg

Experimental

Crystal data

  • C18H12Cl2O2S
  • M r = 363.24
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-o1717-efi1.jpg
  • a = 7.3237 (5) Å
  • b = 9.4919 (6) Å
  • c = 22.4037 (15) Å
  • β = 96.183 (1)°
  • V = 1548.35 (18) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.56 mm−1
  • T = 100 K
  • 0.55 × 0.40 × 0.39 mm

Data collection

  • Bruker APEXII CCD diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2008 [triangle]) T min = 0.748, T max = 0.811
  • 17429 measured reflections
  • 4780 independent reflections
  • 4373 reflections with I > 2σ(I)
  • R int = 0.021

Refinement

  • R[F 2 > 2σ(F 2)] = 0.030
  • wR(F 2) = 0.077
  • S = 0.97
  • 4780 reflections
  • 209 parameters
  • H-atom parameters constrained
  • Δρmax = 0.51 e Å−3
  • Δρmin = −0.26 e Å−3

Data collection: APEX2 (Bruker, 2008 [triangle]); cell refinement: SAINT (Bruker, 2008 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810022725/ci5100sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810022725/ci5100Isup2.hkl

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

Acknowledgments

JPJ thanks Dr Matthias Zeller and the Department of Chemistry, Youngstown State University (YSU), for their assistance with the data collection. The diffractometer was funded by NSF grant No. 0087210, by Ohio Board of Regents grant CAP-491 and by YSU. CSC thanks the University of Mysore for research facilities and HSY thanks the University of Mysore for sabbatical leave.

supplementary crystallographic information

Comment

Thiophenes are important heterocyclic compounds that are widely used as building blocks in many agrochemicals and pharmaceuticals. Thiophene containing compounds are well known to exhibit various biological activities such as antioxidant activity (Ferreira et al., 2006), anti-inflammatory agents and anti-HIV PR inhibitors (Bonini et al., 2005). Thiophene derivatives not only being biologically active (Kulikova et al., 1980), but also show antiradiation activity (Hassan et al., 1998).

The synthesis and antimicrobial evaluation of new chalcones containing 2,5-dichlorothiophene moiety is reported (Tomar et al., 2007). Chalcones have been reported to possess many useful properties, including anti-inflammatory, antimicrobial, antifungal, antioxidant, cytotoxic, antitumor and anticancer activities (Nowakowska et al., 2007). In view of the importance of thiophenes, we report here the crystal structure of the title compound.

In the title molecule, the 2,5-dichloro-3-thienyl and 6-methoxy-2-naphthyl rings are bonded at the opposite ends of the propenone group, the biologically active region (Fig.1). The dihedral angle between mean planes of the dichlorothienyl and naphtyl rings is 2.13 (4)°. The angles between the mean plane of the prop-2-en-1-one group and the mean planes of the thienyl and naphtyl rings are 3.08 (4)°, and 2.88 (4)° repectively. In the crystal, pairs of weak intermolecular C2—H18···O2 hydrogen bonds form dimers and contribute to crystal stability.

Experimental

1-(2,5-Dichlorothiophen-3-yl)ethanone (1.95 g, 0.01 mol) was mixed with 6-methoxy-2-naphthaldehyde (1.86 g, 0.01 mol) and dissolved in ethanol (30 ml). To this, 3 ml of KOH (50%) was added (Fig. 3). The reaction mixture was stirred for 6 h. The resulting crude solid was filtered, washed successively with distilled water and finally recrystallized from ethanol (95%) to give the pure chalcone. Single crystals suitable for X-ray diffraction studies were grown by the slow evaporation of the acetone-toluene (1:1) solution (m.p. 401–403 K).

Refinement

H atoms were placed in their calculated positions and then refined using the riding model with C–H = 0.93 or 0.96 Å, and with Uiso(H) = 1.18–1.50Ueq(C).

Figures

Fig. 1.
Molecular structure of the title compound, showing the atom labeling scheme and 50% probability displacement ellipsoids.
Fig. 2.
Packing diagram of the title compound, viewed down the a axis. Dashed lines indicate weak C—H···O intermolecular interactions which form dimers.
Fig. 3.
Reaction scheme for the title compound.

Crystal data

C18H12Cl2O2SF(000) = 744
Mr = 363.24Dx = 1.558 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 9959 reflections
a = 7.3237 (5) Åθ = 2.3–31.3°
b = 9.4919 (6) ŵ = 0.56 mm1
c = 22.4037 (15) ÅT = 100 K
β = 96.183 (1)°Block, yellow
V = 1548.35 (18) Å30.55 × 0.40 × 0.39 mm
Z = 4

Data collection

Bruker APEXII CCD diffractometer4780 independent reflections
Radiation source: fine-focus sealed tube4373 reflections with I > 2σ(I)
graphiteRint = 0.021
ω scansθmax = 31.4°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2008)h = −10→10
Tmin = 0.748, Tmax = 0.811k = −13→13
17429 measured reflectionsl = −31→31

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)] = 0.030Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.077H-atom parameters constrained
S = 0.97w = 1/[σ2(Fo2) + (0.0374P)2 + 1.0425P] where P = (Fo2 + 2Fc2)/3
4780 reflections(Δ/σ)max = 0.001
209 parametersΔρmax = 0.51 e Å3
0 restraintsΔρmin = −0.26 e Å3

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.
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
Cl10.97320 (4)0.57727 (3)0.666046 (12)0.02001 (7)
Cl21.12452 (4)1.16879 (3)0.677155 (14)0.02261 (7)
S11.08482 (4)0.86262 (3)0.702059 (12)0.01784 (7)
O10.35474 (12)−0.11321 (9)0.30656 (4)0.01761 (16)
O20.81055 (13)0.85374 (9)0.49460 (4)0.02136 (18)
C10.93801 (15)0.81919 (11)0.59314 (5)0.01381 (19)
C20.97881 (15)0.96709 (12)0.59807 (5)0.01517 (19)
H180.95481.03070.56670.018*
C31.05603 (15)1.00339 (12)0.65347 (5)0.0166 (2)
C40.99005 (15)0.75105 (12)0.64645 (5)0.01516 (19)
C50.84960 (15)0.76639 (12)0.53422 (5)0.01448 (19)
C60.81083 (16)0.61554 (12)0.52385 (5)0.0159 (2)
H130.83910.55010.55440.019*
C70.73400 (15)0.57431 (12)0.46967 (5)0.0159 (2)
H120.71280.64480.44090.019*
C80.67971 (15)0.43260 (11)0.45033 (5)0.01457 (19)
C90.70770 (15)0.31296 (12)0.48855 (5)0.01504 (19)
H90.76500.32410.52740.018*
C100.65144 (15)0.18169 (12)0.46900 (5)0.01494 (19)
H80.67090.10500.49470.018*
C110.56360 (14)0.16097 (11)0.40986 (5)0.01316 (19)
C120.53666 (14)0.27935 (11)0.37112 (5)0.01365 (19)
C130.59605 (15)0.41327 (11)0.39266 (5)0.0152 (2)
H110.57830.49070.36730.018*
C140.50474 (15)0.02566 (11)0.38918 (5)0.01431 (19)
H20.5229−0.05220.41430.017*
C150.42044 (15)0.01046 (12)0.33156 (5)0.01419 (19)
C160.39546 (15)0.12772 (12)0.29236 (5)0.0157 (2)
H60.34020.11540.25330.019*
C170.45213 (15)0.25871 (12)0.31159 (5)0.0155 (2)
H50.43530.33500.28550.019*
C180.37100 (18)−0.23386 (13)0.34421 (6)0.0225 (2)
H1A0.4978−0.24870.35860.034*
H1B0.3246−0.31490.32180.034*
H1C0.3016−0.21960.37770.034*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Cl10.02618 (14)0.01646 (13)0.01724 (13)0.00090 (10)0.00169 (10)0.00379 (9)
Cl20.02353 (14)0.01989 (14)0.02423 (14)−0.00595 (10)0.00179 (10)−0.00808 (10)
S10.01786 (13)0.02130 (14)0.01387 (12)−0.00047 (10)−0.00050 (9)−0.00146 (10)
O10.0221 (4)0.0145 (4)0.0154 (4)−0.0021 (3)−0.0015 (3)−0.0017 (3)
O20.0305 (5)0.0157 (4)0.0167 (4)−0.0021 (3)−0.0032 (3)0.0020 (3)
C10.0133 (4)0.0139 (4)0.0142 (4)−0.0005 (3)0.0019 (3)−0.0009 (4)
C20.0150 (5)0.0142 (5)0.0163 (5)−0.0010 (4)0.0016 (4)−0.0012 (4)
C30.0154 (5)0.0164 (5)0.0181 (5)−0.0025 (4)0.0022 (4)−0.0029 (4)
C40.0150 (5)0.0154 (5)0.0151 (5)−0.0006 (4)0.0016 (4)−0.0007 (4)
C50.0143 (5)0.0147 (5)0.0145 (4)−0.0014 (4)0.0017 (3)−0.0010 (4)
C60.0189 (5)0.0129 (5)0.0156 (5)−0.0005 (4)0.0009 (4)0.0005 (4)
C70.0173 (5)0.0141 (5)0.0161 (5)−0.0003 (4)0.0015 (4)0.0000 (4)
C80.0145 (5)0.0139 (5)0.0154 (5)−0.0005 (4)0.0020 (4)−0.0006 (4)
C90.0163 (5)0.0156 (5)0.0128 (4)−0.0007 (4)−0.0004 (4)−0.0003 (4)
C100.0164 (5)0.0146 (5)0.0134 (4)0.0003 (4)−0.0004 (4)0.0016 (4)
C110.0122 (4)0.0142 (5)0.0131 (4)0.0002 (3)0.0013 (3)−0.0002 (3)
C120.0127 (4)0.0148 (5)0.0135 (4)0.0008 (4)0.0012 (3)0.0000 (4)
C130.0170 (5)0.0135 (5)0.0148 (5)0.0001 (4)0.0010 (4)0.0014 (4)
C140.0154 (5)0.0138 (5)0.0134 (4)0.0000 (4)0.0003 (3)0.0004 (4)
C150.0131 (4)0.0147 (5)0.0148 (5)−0.0003 (4)0.0018 (3)−0.0019 (4)
C160.0152 (5)0.0187 (5)0.0130 (4)0.0007 (4)0.0000 (4)−0.0006 (4)
C170.0166 (5)0.0170 (5)0.0126 (4)0.0007 (4)0.0004 (4)0.0016 (4)
C180.0285 (6)0.0152 (5)0.0223 (6)−0.0033 (4)−0.0042 (5)0.0007 (4)

Geometric parameters (Å, °)

Cl1—C41.7148 (12)C9—C101.3694 (15)
Cl2—C31.7148 (12)C9—H90.93
S1—C31.7220 (12)C10—C111.4230 (15)
S1—C41.7231 (11)C10—H80.93
O1—C151.3657 (13)C11—C141.4167 (15)
O1—C181.4198 (14)C11—C121.4206 (15)
O2—C51.2257 (14)C12—C131.4116 (15)
C1—C41.3756 (15)C12—C171.4220 (15)
C1—C21.4371 (15)C13—H110.93
C1—C51.4930 (15)C14—C151.3772 (15)
C2—C31.3519 (15)C14—H20.93
C2—H180.93C15—C161.4174 (15)
C5—C61.4732 (15)C16—C171.3658 (16)
C6—C71.3403 (15)C16—H60.93
C6—H130.93C17—H50.93
C7—C81.4553 (15)C18—H1A0.96
C7—H120.93C18—H1B0.96
C8—C131.3811 (15)C18—H1C0.96
C8—C91.4238 (15)
C3—S1—C490.43 (5)C9—C10—H8119.5
C15—O1—C18116.50 (9)C11—C10—H8119.5
C4—C1—C2110.89 (10)C14—C11—C12120.00 (10)
C4—C1—C5131.54 (10)C14—C11—C10121.40 (10)
C2—C1—C5117.57 (10)C12—C11—C10118.60 (10)
C3—C2—C1112.49 (10)C13—C12—C11119.07 (10)
C3—C2—H18123.8C13—C12—C17122.12 (10)
C1—C2—H18123.8C11—C12—C17118.80 (10)
C2—C3—Cl2126.65 (9)C8—C13—C12121.93 (10)
C2—C3—S1113.15 (9)C8—C13—H11119.0
Cl2—C3—S1120.20 (7)C12—C13—H11119.0
C1—C4—Cl1130.82 (9)C15—C14—C11119.43 (10)
C1—C4—S1113.03 (8)C15—C14—H2120.3
Cl1—C4—S1116.14 (6)C11—C14—H2120.3
O2—C5—C6121.16 (10)O1—C15—C14125.24 (10)
O2—C5—C1117.28 (10)O1—C15—C16113.86 (9)
C6—C5—C1121.57 (10)C14—C15—C16120.89 (10)
C7—C6—C5118.79 (10)C17—C16—C15120.32 (10)
C7—C6—H13120.6C17—C16—H6119.8
C5—C6—H13120.6C15—C16—H6119.8
C6—C7—C8127.89 (10)C16—C17—C12120.54 (10)
C6—C7—H12116.1C16—C17—H5119.7
C8—C7—H12116.1C12—C17—H5119.7
C13—C8—C9118.50 (10)O1—C18—H1A109.5
C13—C8—C7118.74 (10)O1—C18—H1B109.5
C9—C8—C7122.76 (10)H1A—C18—H1B109.5
C10—C9—C8120.97 (10)O1—C18—H1C109.5
C10—C9—H9119.5H1A—C18—H1C109.5
C8—C9—H9119.5H1B—C18—H1C109.5
C9—C10—C11120.92 (10)
C4—C1—C2—C3−0.59 (14)C8—C9—C10—C110.10 (17)
C5—C1—C2—C3179.12 (10)C9—C10—C11—C14−179.96 (10)
C1—C2—C3—Cl2179.91 (8)C9—C10—C11—C120.54 (16)
C1—C2—C3—S10.38 (13)C14—C11—C12—C13179.89 (10)
C4—S1—C3—C2−0.07 (9)C10—C11—C12—C13−0.61 (15)
C4—S1—C3—Cl2−179.63 (8)C14—C11—C12—C17−0.70 (16)
C2—C1—C4—Cl1179.61 (9)C10—C11—C12—C17178.80 (10)
C5—C1—C4—Cl1−0.04 (19)C9—C8—C13—C120.61 (17)
C2—C1—C4—S10.53 (12)C7—C8—C13—C12−178.84 (10)
C5—C1—C4—S1−179.12 (10)C11—C12—C13—C80.03 (16)
C3—S1—C4—C1−0.28 (9)C17—C12—C13—C8−179.36 (10)
C3—S1—C4—Cl1−179.50 (7)C12—C11—C14—C15−0.45 (16)
C4—C1—C5—O2176.66 (12)C10—C11—C14—C15−179.94 (10)
C2—C1—C5—O2−2.97 (15)C18—O1—C15—C141.95 (16)
C4—C1—C5—C6−3.43 (18)C18—O1—C15—C16−178.24 (10)
C2—C1—C5—C6176.94 (10)C11—C14—C15—O1−178.83 (10)
O2—C5—C6—C71.01 (17)C11—C14—C15—C161.37 (16)
C1—C5—C6—C7−178.90 (10)O1—C15—C16—C17179.05 (10)
C5—C6—C7—C8−178.11 (11)C14—C15—C16—C17−1.13 (17)
C6—C7—C8—C13177.68 (12)C15—C16—C17—C12−0.06 (17)
C6—C7—C8—C9−1.74 (19)C13—C12—C17—C16−179.65 (10)
C13—C8—C9—C10−0.68 (17)C11—C12—C17—C160.96 (16)
C7—C8—C9—C10178.74 (11)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C2—H18···O2i0.932.563.2051 (14)127

Symmetry codes: (i) −x+2, −y+2, −z+1.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CI5100).

References

  • Bonini, C., Chiummiento, L., Bonis, M. D., Funicello, M., Lupattelli, P., Suanno, G., Brault, L., Migianu, E., Neguesque, A., Battagalia, E., Bagrel, D. & Kirsch, G. (2005). Eur. J. Med. Chem.40, 757–763. [PubMed]
  • Bruker (2008). APEX2, SAINT and SADABS Bruker AXS Inc., Madison, Wisconsin, USA
  • Butcher, R. J., Yathirajan, H. S., Ashalatha, B. V., Narayana, B. & Sarojini, B. K. (2007). Acta Cryst. E63, o1430–o1431.
  • Ferreira, I. C. F. R., Queiroz, M. R. P., Vilas-Boas, M., Estevinho, L. M., Begouin, A. & Kirsch, G. (2006). Bioorg. Med. Chem. Lett.16, 1384–1387. [PubMed]
  • Harrison, W. T. A., Ashalatha, B. V., Narayana, B., Sarojini, B. K. & Yathirajan, H. S. (2007a). Acta Cryst. E63, o4183.
  • Harrison, W. T. A., Ashalatha, B. V., Narayana, B., Sarojini, B. K. & Yathirajan, H. S. (2007b). Acta Cryst. E63, o3898.
  • Hassan, A. Y., Ghorab, M. M. & Nassar, O. M. (1998). Phosphorus Sulfur Silicon Relat. Elem.134, 77–86.
  • Kulikova, D. A., Churkin, Y. D. & Panfilova, L. V. (1980). Pharm. Chem. J.14, 227–229.
  • Li, H., Mayekar, A. N., Narayana, B., Yathirajan, H. S. & Harrison, W. T. A. (2009). Acta Cryst. E65, o1533. [PMC free article] [PubMed]
  • Nowakowska, Z. (2007). Eur. J. Med. Chem.42, 125–137. [PubMed]
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Spek, A. L. (2009). Acta Cryst. D65, 148–155. [PMC free article] [PubMed]
  • Tomar, V., Bhattacharjee, G., Kamaluddin & Kumar, A. (2007). Bioorg. Med. Chem. Lett.17, 5321–5324. [PubMed]
  • Yathirajan, H. S., Narayana, B., Ashalatha, B., Sarojini, B. K. & Bolte, M. (2006). Acta Cryst. E62, o4440–o4441.

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