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The geometric parameters of the title compound, C13H7Cl3OS, are in the usual ranges. The mol­ecule is almost planar (r.m.s. deviation of all non-H atoms 0.193 Å). The dihedral angle between the two aromatic rings is 14.41 (7)°. The C=C double bond is trans configured. The bond between the carbonyl bond and the thienyl ring is in an eclipsed conformation. The crystal packing is stabilized by a weak C—H...O hydrogen bond.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807051768/at2441sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807051768/at2441Isup2.hkl
Contains datablock I

CCDC reference: 667430

Key indicators

  • Single-crystal X-ray study
  • T = 173 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.032
  • wR factor = 0.088
  • Data-to-parameter ratio = 23.0

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT230_ALERT_2_B Hirshfeld Test Diff for C5 - C6 .. 7.80 su
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 0 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Comment top

Chalcones, 1,3-diphenyl-1-propan-3-one derivatives, have a wide range of biological properties, including anticancer (Achanta et al., 2006; Kim, Choi et al., 2006), antiproliferative (Hsu et al., 2006), anti malarial (Wirasathien et al., 2006), anti inflammatory (Anuradha et al., 2006), anti-allergic (Daikonya et al., 2004) and antagonist (Kim, Kim et al., 2006). Chalcones exhibit inhibitory activity against nitric oxide production (Han et al., 2006), dengue 2 virus NS3 protease (Kiat et al., 2006) and tyrosinase (Khatib et al., 2005). Some chalcone derivatives exhibit nonlinear optical properties (Gao & Ng, 2006). Thiophene analogues of antiviral chalcones have been studied (Binder et al., 1985). The crystal structures of (2E)-1-(3-bromo-2-thienyl)-3-(4-chlorophenyl)prop-2-en-1-one (Yathirajan, Ashalatha et al., 2006), (2E)-1-(3-bromo-2-thienyl)-3-(4-methoxy-2,3,6-trimethylphenyl)prop-2-en-1-one (Yathirajan, Narayana et al., 2006), (2E)-1-(3-methyl-2-thienyl)-3-(3-nitrophenyl)prop-2-en-1-one (Sarojini et al., 2007) and (2E)-1-(3-methyl-2-thienyl)-3-(3-nitrophenyl)prop-2-en-1-one(Yathirajan et al., 2007), have been reported. The structure determination of the title compound was undertaken as a part of our study on chalcones and related derivatives.

Geometric parameters of the title compound are in the usual ranges. The molecule is almost planar (r.m.s. deviation of all non-H atoms 0.193 Å). The C–C double bond is trans configured. The bond between the carbonyl bond and the thienyl ring is in an eclipsed conformation. The crystal packing is stabilized by a weak C—H···O hydrogen bond.

Related literature top

For related literature, see: Achanta et al. (2006); Anuradha et al. (2006); Binder et al. (1985); Daikonya et al. (2004); Gao & Ng (2006); Han et al. (2006); Hsu et al. (2006); Khatib et al. (2005); Kiat et al. (2006); Kim, Choi et al. (2006); Kim, Kim et al. (2006); Sarojini et al. (2007); Wirasathien et al. (2006); Yathirajan et al. (2007); Yathirajan, Ashalatha et al. (2006); Yathirajan, Narayana et al. (2006).

Experimental top

The title compound was prepared by the Claisen-Schmidt condensation of equimolar quantities of 1-(2-thienyl)ethanone (1.26 g, 0.01 mol) and 2,3,5-trichlorobenzaldehyde (2.09 g, 0.01 mol) in ethanol (25 ml), in the presence of sodium hydroxide (8 ml, 10%) (see reaction scheme). The product was recrystallized from ethyl acetate by slow evaporation [m.p.: 378 K]. Analysis for C13H7Cl3OS: Found (Calculated) C 49.10 (49.16), H 2.19 (2.22), S 10.02% (10.10%).

Refinement top

All H atoms were found in a difference map, but geometrically positioned and refined with fixed individual displacement parameters [U(H) = 1.2 Ueq(C)] using a riding model with C—H = 0.95 Å.

Structure description top

Chalcones, 1,3-diphenyl-1-propan-3-one derivatives, have a wide range of biological properties, including anticancer (Achanta et al., 2006; Kim, Choi et al., 2006), antiproliferative (Hsu et al., 2006), anti malarial (Wirasathien et al., 2006), anti inflammatory (Anuradha et al., 2006), anti-allergic (Daikonya et al., 2004) and antagonist (Kim, Kim et al., 2006). Chalcones exhibit inhibitory activity against nitric oxide production (Han et al., 2006), dengue 2 virus NS3 protease (Kiat et al., 2006) and tyrosinase (Khatib et al., 2005). Some chalcone derivatives exhibit nonlinear optical properties (Gao & Ng, 2006). Thiophene analogues of antiviral chalcones have been studied (Binder et al., 1985). The crystal structures of (2E)-1-(3-bromo-2-thienyl)-3-(4-chlorophenyl)prop-2-en-1-one (Yathirajan, Ashalatha et al., 2006), (2E)-1-(3-bromo-2-thienyl)-3-(4-methoxy-2,3,6-trimethylphenyl)prop-2-en-1-one (Yathirajan, Narayana et al., 2006), (2E)-1-(3-methyl-2-thienyl)-3-(3-nitrophenyl)prop-2-en-1-one (Sarojini et al., 2007) and (2E)-1-(3-methyl-2-thienyl)-3-(3-nitrophenyl)prop-2-en-1-one(Yathirajan et al., 2007), have been reported. The structure determination of the title compound was undertaken as a part of our study on chalcones and related derivatives.

Geometric parameters of the title compound are in the usual ranges. The molecule is almost planar (r.m.s. deviation of all non-H atoms 0.193 Å). The C–C double bond is trans configured. The bond between the carbonyl bond and the thienyl ring is in an eclipsed conformation. The crystal packing is stabilized by a weak C—H···O hydrogen bond.

For related literature, see: Achanta et al. (2006); Anuradha et al. (2006); Binder et al. (1985); Daikonya et al. (2004); Gao & Ng (2006); Han et al. (2006); Hsu et al. (2006); Khatib et al. (2005); Kiat et al. (2006); Kim, Choi et al. (2006); Kim, Kim et al. (2006); Sarojini et al. (2007); Wirasathien et al. (2006); Yathirajan et al. (2007); Yathirajan, Ashalatha et al. (2006); Yathirajan, Narayana et al. (2006).

Computing details top

Data collection: X-AREA (Stoe & Cie, 2001); cell refinement: X-AREA (Stoe & Cie, 2001); data reduction: X-AREA (Stoe & Cie, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP in SHELXTL-Plus (Sheldrick, 1991); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).

Figures top
[Figure 1] Fig. 1. Perspective view of the title compound with the atom numbering; displacement ellipsoids are at the 50% probability level.
[Figure 2] Fig. 2. The formation of the title compound.
(2E)-1-(2-Thienyl)-3-(2,3,5-trichlorophenyl)prop-2-en-1-one top
Crystal data top
C13H7Cl3OSF(000) = 640
Mr = 317.60Dx = 1.594 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 21250 reflections
a = 16.7102 (11) Åθ = 3.8–29.8°
b = 7.5130 (4) ŵ = 0.83 mm1
c = 10.8805 (8) ÅT = 173 K
β = 104.395 (5)°Block, colourless
V = 1323.09 (15) Å30.31 × 0.25 × 0.19 mm
Z = 4
Data collection top
Stoe IPDSII two-circle
diffractometer
3764 independent reflections
Radiation source: fine-focus sealed tube3276 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.037
ω scansθmax = 29.8°, θmin = 3.7°
Absorption correction: multi-scan
(MULABS; Spek, 2003; Blessing, 1995)
h = 2323
Tmin = 0.783, Tmax = 0.858k = 1010
20538 measured reflectionsl = 1515
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.032H-atom parameters constrained
wR(F2) = 0.088 w = 1/[σ2(Fo2) + (0.0505P)2 + 0.3998P]
where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max = 0.001
3764 reflectionsΔρmax = 0.37 e Å3
164 parametersΔρmin = 0.40 e Å3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0137 (17)
Crystal data top
C13H7Cl3OSV = 1323.09 (15) Å3
Mr = 317.60Z = 4
Monoclinic, P21/cMo Kα radiation
a = 16.7102 (11) ŵ = 0.83 mm1
b = 7.5130 (4) ÅT = 173 K
c = 10.8805 (8) Å0.31 × 0.25 × 0.19 mm
β = 104.395 (5)°
Data collection top
Stoe IPDSII two-circle
diffractometer
3764 independent reflections
Absorption correction: multi-scan
(MULABS; Spek, 2003; Blessing, 1995)
3276 reflections with I > 2σ(I)
Tmin = 0.783, Tmax = 0.858Rint = 0.037
20538 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0320 restraints
wR(F2) = 0.088H-atom parameters constrained
S = 1.04Δρmax = 0.37 e Å3
3764 reflectionsΔρmin = 0.40 e Å3
164 parameters
Special details top

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) top
xyzUiso*/Ueq
Cl10.87602 (2)0.58544 (6)0.89280 (3)0.03789 (11)
Cl21.01174 (2)0.38496 (6)0.79526 (4)0.04403 (12)
Cl30.81790 (3)0.39170 (6)0.31918 (4)0.04020 (12)
S10.42317 (2)0.91675 (6)0.66226 (4)0.03423 (11)
O10.60078 (7)0.86595 (15)0.78673 (9)0.0314 (2)
C10.71879 (8)0.67660 (18)0.69127 (12)0.0242 (2)
H10.73240.71700.77670.029*
C20.64235 (8)0.71009 (19)0.62167 (12)0.0251 (2)
H20.62670.67430.53530.030*
C30.58164 (8)0.80322 (17)0.67877 (12)0.0231 (2)
C40.49649 (8)0.81260 (17)0.60132 (12)0.0223 (2)
C50.46220 (8)0.74799 (18)0.47791 (12)0.0242 (2)
H50.49230.68560.42800.029*
C60.37602 (9)0.7891 (2)0.43787 (15)0.0338 (3)
H60.34210.75770.35700.041*
C70.34764 (10)0.8780 (2)0.52797 (16)0.0359 (3)
H70.29180.91430.51690.043*
C110.78359 (8)0.58274 (17)0.64720 (12)0.0226 (2)
C120.85862 (8)0.53493 (18)0.73275 (12)0.0253 (2)
C130.91959 (8)0.44393 (19)0.69000 (14)0.0283 (3)
C140.90810 (9)0.39832 (19)0.56313 (14)0.0294 (3)
H140.94960.33640.53440.035*
C150.83386 (8)0.44621 (19)0.47927 (13)0.0264 (3)
C160.77229 (8)0.53606 (18)0.51859 (12)0.0243 (2)
H160.72230.56630.45880.029*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.03548 (19)0.0486 (2)0.02455 (17)0.00456 (15)0.00205 (13)0.00448 (14)
Cl20.02560 (18)0.0533 (3)0.0459 (2)0.01070 (15)0.00474 (15)0.00116 (18)
Cl30.0422 (2)0.0515 (2)0.02833 (18)0.01138 (16)0.01151 (14)0.00645 (15)
S10.03290 (19)0.0422 (2)0.03047 (18)0.01007 (14)0.01326 (14)0.00051 (14)
O10.0322 (5)0.0395 (6)0.0224 (4)0.0022 (4)0.0068 (4)0.0056 (4)
C10.0251 (6)0.0262 (6)0.0214 (5)0.0010 (4)0.0064 (4)0.0001 (4)
C20.0248 (6)0.0302 (6)0.0209 (5)0.0021 (5)0.0067 (4)0.0010 (5)
C30.0252 (6)0.0243 (6)0.0207 (5)0.0012 (4)0.0075 (4)0.0020 (4)
C40.0243 (6)0.0223 (6)0.0223 (5)0.0029 (4)0.0093 (4)0.0019 (4)
C50.0206 (5)0.0308 (6)0.0208 (5)0.0025 (4)0.0045 (4)0.0005 (5)
C60.0271 (6)0.0386 (8)0.0326 (7)0.0003 (6)0.0018 (5)0.0004 (6)
C70.0255 (6)0.0404 (8)0.0427 (8)0.0060 (6)0.0102 (6)0.0078 (6)
C110.0212 (5)0.0231 (6)0.0231 (5)0.0008 (4)0.0049 (4)0.0018 (4)
C120.0233 (6)0.0264 (6)0.0242 (6)0.0013 (4)0.0024 (5)0.0007 (5)
C130.0205 (6)0.0282 (6)0.0337 (7)0.0011 (5)0.0018 (5)0.0018 (5)
C140.0237 (6)0.0292 (6)0.0358 (7)0.0026 (5)0.0085 (5)0.0009 (5)
C150.0265 (6)0.0277 (6)0.0258 (6)0.0008 (5)0.0079 (5)0.0011 (5)
C160.0226 (5)0.0268 (6)0.0232 (5)0.0017 (4)0.0054 (4)0.0015 (5)
Geometric parameters (Å, º) top
Cl1—C121.7348 (14)C5—C61.4308 (19)
Cl2—C131.7327 (14)C5—H50.9500
Cl3—C151.7441 (14)C6—C71.365 (2)
S1—C71.7016 (18)C6—H60.9500
S1—C41.7196 (13)C7—H70.9500
O1—C31.2318 (16)C11—C161.4090 (18)
C1—C21.3370 (18)C11—C121.4096 (17)
C1—C111.4691 (18)C12—C131.3990 (19)
C1—H10.9500C13—C141.389 (2)
C2—C31.4893 (18)C14—C151.3921 (19)
C2—H20.9500C14—H140.9500
C3—C41.4641 (18)C15—C161.3844 (18)
C4—C51.4087 (17)C16—H160.9500
C7—S1—C492.21 (7)C6—C7—H7123.7
C2—C1—C11125.69 (12)S1—C7—H7123.7
C2—C1—H1117.2C16—C11—C12118.04 (12)
C11—C1—H1117.2C16—C11—C1121.06 (11)
C1—C2—C3120.40 (12)C12—C11—C1120.90 (12)
C1—C2—H2119.8C13—C12—C11120.44 (12)
C3—C2—H2119.8C13—C12—Cl1119.11 (10)
O1—C3—C4121.01 (12)C11—C12—Cl1120.44 (10)
O1—C3—C2122.36 (12)C14—C13—C12121.27 (12)
C4—C3—C2116.60 (11)C14—C13—Cl2118.33 (11)
C5—C4—C3129.70 (11)C12—C13—Cl2120.40 (11)
C5—C4—S1111.37 (9)C13—C14—C15117.92 (13)
C3—C4—S1118.92 (9)C13—C14—H14121.0
C4—C5—C6110.85 (12)C15—C14—H14121.0
C4—C5—H5124.6C16—C15—C14122.22 (13)
C6—C5—H5124.6C16—C15—Cl3118.83 (10)
C7—C6—C5112.95 (13)C14—C15—Cl3118.95 (11)
C7—C6—H6123.5C15—C16—C11120.12 (12)
C5—C6—H6123.5C15—C16—H16119.9
C6—C7—S1112.61 (11)C11—C16—H16119.9
C11—C1—C2—C3178.59 (12)C16—C11—C12—C130.05 (19)
C1—C2—C3—O16.4 (2)C1—C11—C12—C13179.34 (12)
C1—C2—C3—C4171.87 (12)C16—C11—C12—Cl1179.07 (10)
O1—C3—C4—C5179.18 (14)C1—C11—C12—Cl10.22 (18)
C2—C3—C4—C50.9 (2)C11—C12—C13—C140.0 (2)
O1—C3—C4—S11.18 (18)Cl1—C12—C13—C14179.10 (11)
C2—C3—C4—S1179.47 (9)C11—C12—C13—Cl2179.92 (10)
C7—S1—C4—C50.21 (11)Cl1—C12—C13—Cl20.79 (17)
C7—S1—C4—C3179.49 (11)C12—C13—C14—C150.1 (2)
C3—C4—C5—C6179.12 (13)Cl2—C13—C14—C15179.98 (11)
S1—C4—C5—C60.54 (15)C13—C14—C15—C160.2 (2)
C4—C5—C6—C70.70 (19)C13—C14—C15—Cl3179.67 (11)
C5—C6—C7—S10.55 (19)C14—C15—C16—C110.2 (2)
C4—S1—C7—C60.19 (13)Cl3—C15—C16—C11179.66 (10)
C2—C1—C11—C167.3 (2)C12—C11—C16—C150.13 (19)
C2—C1—C11—C12171.96 (13)C1—C11—C16—C15179.42 (12)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C16—H16···O1i0.952.453.3948 (17)174
Symmetry code: (i) x, y+3/2, z1/2.

Experimental details

Crystal data
Chemical formulaC13H7Cl3OS
Mr317.60
Crystal system, space groupMonoclinic, P21/c
Temperature (K)173
a, b, c (Å)16.7102 (11), 7.5130 (4), 10.8805 (8)
β (°) 104.395 (5)
V3)1323.09 (15)
Z4
Radiation typeMo Kα
µ (mm1)0.83
Crystal size (mm)0.31 × 0.25 × 0.19
Data collection
DiffractometerStoe IPDSII two-circle
Absorption correctionMulti-scan
(MULABS; Spek, 2003; Blessing, 1995)
Tmin, Tmax0.783, 0.858
No. of measured, independent and
observed [I > 2σ(I)] reflections
20538, 3764, 3276
Rint0.037
(sin θ/λ)max1)0.698
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.032, 0.088, 1.04
No. of reflections3764
No. of parameters164
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.37, 0.40

Computer programs: X-AREA (Stoe & Cie, 2001), SHELXS97 (Sheldrick, 1990), SHELXL97 (Sheldrick, 1997), XP in SHELXTL-Plus (Sheldrick, 1991).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C16—H16···O1i0.952.453.3948 (17)173.8
Symmetry code: (i) x, y+3/2, z1/2.
 

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