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Geometric parameters of the title compound, C16H14O2S, a chalcone derivative, are in the usual ranges. The C=C double bond has a trans configuration. The essentially planar mol­ecules (r.m.s. deviation for all non-H atoms = 0.034 Å) crystallize in planes parallel to the (\overline{1}40) plane. The mol­ecular conformation is stabilized by an O—H...O hydrogen bond. The investigated crystal was a non-merohedral twin with a ratio of the twin components of 0.254 (1):0.746 (1).

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807052312/at2443sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807052312/at2443Isup2.hkl
Contains datablock I

CCDC reference: 667452

Key indicators

  • Single-crystal X-ray study
  • T = 173 K
  • R factor = 0.057
  • wR factor = 0.184
  • Data-to-parameter ratio = 15.7

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Comment top

Chalcones are a class of naturally occurring compounds with various biological activities. They are known as the precursors of all flavonoid type natural products in biosynthesis. Chalcones can be easily obtained from the aldol condensation of aromatic aldehydes and aromatic ketones. This class of compounds presents interesting biological properties such as cytotoxicity (Pandey et al., 2005) and antiherpes activity and antitumour activity (Conti, 2006) and may be useful for the chemotherapy of leishmaniasis among others (Lawrence et al., 2001). Chalcone derivatives are also used as antibiotics (Nielsen et al., 2005) and as anti malerials (Domínguez et al., 2005). Chalcone derivatives are recognized for NLO properties and have good crystallization ability (Goto et al. 1991; Indira et al. 2002; Sarojini et al., 2006). Structures of few related chalcones viz. (2E)-1-(2,4-dichlorophenyl)-3-(2-hydroxy-3-methoxyphenyl)prop-2-en-1-one (Yathirajan, Mayekar, Narayana, et al., 2007), (2E)-1-(2,4-dichlorophenyl)-3-(2-hydroxyphenyl)prop-2-en-1-one (Yathirajan, Mayekar, Sarojini, et al. 2007), 3-[4-(methylsulfanyl)phenyl]-1-(4-nitrophenyl)prop-2-en-1-one (Harrison, Yathirajan, Mithun et al., 2006), 2E)-1-(3-hydroxyphenyl)-3-(4-methylphenyl)prop-2-en-1-one (Butcher et al. 2007). In continuation of our studies on chalcones, a new chalcone, C16H14O2S, has been synthesized and its crystal structure is reported.

Geometric parameters of the title compound are in the usual ranges. The C—C double bond is trans configured. The essentially planar molecules [r.m.s. deviation for all non-H atoms 0.034 Å] crystallize in planes parallel to the (-1 4 0) plane. The molecular conformation is stabilized by a O—H···O hydrogen bond. The investigated crystal was a non-merohedral twin with a ratio of the twin components of 0.254 (1)/0.746 (1).

Related literature top

For related literature, see: Butcher et al. (2007); Conti (2006); Domínguez et al. (2005); Goto et al. (1991); Harrison et al. (2006); Indira et al. (2002); Lawrence et al. (2001); Nielsen et al. (2005); Pandey et al. (2005); Sarojini et al. (2006); Yathirajan, Mayekar, Narayana et al. (2007); Yathirajan, Mayekar, Sarojini, et al. (2007).

Experimental top

To a solution of 2-hydroxyacetophenone (1.36 g, 0.01 mol) and 4-methylthiobenzaldehyde (1.52 g, 0.01 mol) in 20 ml of ethanol, 50% KOH (2.5 ml) was added at 273 K. The mixture was stirred overnight at room temperature and then poured on to ice water. The pH of this mixture was adjusted to 3–4 with 2 M HCl aqueous solution. A yellow precipitate was collected by filtration and purified by recrystallization in ethanol. The single crystals were grown from acetone by slow evaporation method. [m.p.: 338–343 K]. Analysis for C16H14O2S: Found (Calculated): C 71.18 (71.08), H 5.25 (5.22), S 11.89% (11.86%).

Refinement top

All H atoms were found in a difference map, but those bonded to C were geometrically positioned and refined with fixed individual displacement parameters [U(H) = 1.2 Ueq(C) or U(H) = 1.5 Ueq(Cmethyl)] using a riding model with C—H = 0.95 Å or 0.98 Å for Caromatic—H and Cmethyl—H, respectively. The hydroxyl H atom was freely refined. The investigated crystal was a non-merohedral twin with a ratio of the twin components of 0.254 (1)/0.746 (1).

Structure description top

Chalcones are a class of naturally occurring compounds with various biological activities. They are known as the precursors of all flavonoid type natural products in biosynthesis. Chalcones can be easily obtained from the aldol condensation of aromatic aldehydes and aromatic ketones. This class of compounds presents interesting biological properties such as cytotoxicity (Pandey et al., 2005) and antiherpes activity and antitumour activity (Conti, 2006) and may be useful for the chemotherapy of leishmaniasis among others (Lawrence et al., 2001). Chalcone derivatives are also used as antibiotics (Nielsen et al., 2005) and as anti malerials (Domínguez et al., 2005). Chalcone derivatives are recognized for NLO properties and have good crystallization ability (Goto et al. 1991; Indira et al. 2002; Sarojini et al., 2006). Structures of few related chalcones viz. (2E)-1-(2,4-dichlorophenyl)-3-(2-hydroxy-3-methoxyphenyl)prop-2-en-1-one (Yathirajan, Mayekar, Narayana, et al., 2007), (2E)-1-(2,4-dichlorophenyl)-3-(2-hydroxyphenyl)prop-2-en-1-one (Yathirajan, Mayekar, Sarojini, et al. 2007), 3-[4-(methylsulfanyl)phenyl]-1-(4-nitrophenyl)prop-2-en-1-one (Harrison, Yathirajan, Mithun et al., 2006), 2E)-1-(3-hydroxyphenyl)-3-(4-methylphenyl)prop-2-en-1-one (Butcher et al. 2007). In continuation of our studies on chalcones, a new chalcone, C16H14O2S, has been synthesized and its crystal structure is reported.

Geometric parameters of the title compound are in the usual ranges. The C—C double bond is trans configured. The essentially planar molecules [r.m.s. deviation for all non-H atoms 0.034 Å] crystallize in planes parallel to the (-1 4 0) plane. The molecular conformation is stabilized by a O—H···O hydrogen bond. The investigated crystal was a non-merohedral twin with a ratio of the twin components of 0.254 (1)/0.746 (1).

For related literature, see: Butcher et al. (2007); Conti (2006); Domínguez et al. (2005); Goto et al. (1991); Harrison et al. (2006); Indira et al. (2002); Lawrence et al. (2001); Nielsen et al. (2005); Pandey et al. (2005); Sarojini et al. (2006); Yathirajan, Mayekar, Narayana et al. (2007); Yathirajan, Mayekar, Sarojini, et al. (2007).

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-Hydroxyphenyl)-3-[4-(methylsulfanyl)phenyl]prop-2-en-1-one top
Crystal data top
C16H14O2SZ = 2
Mr = 270.33F(000) = 284
Triclinic, P1Dx = 1.332 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 6.6516 (9) ÅCell parameters from 5613 reflections
b = 7.0223 (11) Åθ = 3.7–26.1°
c = 15.0248 (17) ŵ = 0.23 mm1
α = 90.789 (11)°T = 173 K
β = 93.409 (11)°Plate, yellow
γ = 105.718 (12)°0.37 × 0.31 × 0.12 mm
V = 673.98 (16) Å3
Data collection top
Stoe IPDSII two-circle
diffractometer
2807 independent reflections
Radiation source: fine-focus sealed tube2451 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.077
ω scansθmax = 26.6°, θmin = 3.6°
Absorption correction: multi-scan
(MULABS; Spek, 2003; Blessing, 1995)
h = 88
Tmin = 0.938, Tmax = 0.982k = 88
13663 measured reflectionsl = 1818
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)] = 0.057H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.184 w = 1/[σ2(Fo2) + (0.103P)2 + 0.6276P]
where P = (Fo2 + 2Fc2)/3
S = 1.10(Δ/σ)max < 0.001
2807 reflectionsΔρmax = 0.59 e Å3
179 parametersΔρmin = 0.43 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: 0.056 (11)
Crystal data top
C16H14O2Sγ = 105.718 (12)°
Mr = 270.33V = 673.98 (16) Å3
Triclinic, P1Z = 2
a = 6.6516 (9) ÅMo Kα radiation
b = 7.0223 (11) ŵ = 0.23 mm1
c = 15.0248 (17) ÅT = 173 K
α = 90.789 (11)°0.37 × 0.31 × 0.12 mm
β = 93.409 (11)°
Data collection top
Stoe IPDSII two-circle
diffractometer
2807 independent reflections
Absorption correction: multi-scan
(MULABS; Spek, 2003; Blessing, 1995)
2451 reflections with I > 2σ(I)
Tmin = 0.938, Tmax = 0.982Rint = 0.077
13663 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0570 restraints
wR(F2) = 0.184H atoms treated by a mixture of independent and constrained refinement
S = 1.10Δρmax = 0.59 e Å3
2807 reflectionsΔρmin = 0.43 e Å3
179 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
S10.96299 (11)0.85185 (11)0.24466 (4)0.0293 (3)
O10.0262 (3)0.6428 (3)0.64803 (13)0.0311 (5)
O20.1191 (3)0.6145 (3)0.80106 (15)0.0341 (5)
H2O0.117 (8)0.615 (8)0.746 (3)0.072 (15)*
C10.2112 (4)0.6915 (4)0.68040 (17)0.0219 (5)
C20.3848 (4)0.7324 (4)0.62090 (17)0.0238 (5)
H20.52520.77880.64520.029*
C30.3447 (4)0.7040 (4)0.53205 (17)0.0230 (5)
H30.20150.65610.51170.028*
C110.2534 (4)0.7082 (4)0.77907 (17)0.0224 (5)
C120.0818 (4)0.6681 (4)0.83462 (18)0.0256 (6)
C130.1188 (5)0.6841 (4)0.92739 (19)0.0334 (7)
H130.00400.66080.96430.040*
C140.3208 (6)0.7333 (5)0.96593 (19)0.0383 (7)
H140.34380.74191.02900.046*
C150.4904 (5)0.7705 (5)0.91268 (19)0.0377 (7)
H150.62910.80400.93930.045*
C160.4565 (4)0.7584 (4)0.82031 (18)0.0296 (6)
H160.57310.78470.78440.036*
C210.4959 (4)0.7383 (4)0.46331 (16)0.0216 (5)
C220.4208 (4)0.7199 (4)0.37357 (17)0.0247 (5)
H220.27390.68410.35940.030*
C230.5558 (4)0.7527 (4)0.30451 (16)0.0249 (5)
H230.50110.73970.24420.030*
C240.7725 (4)0.8047 (4)0.32437 (16)0.0218 (5)
C250.8500 (4)0.8217 (4)0.41452 (17)0.0231 (5)
H250.99670.85640.42870.028*
C260.7137 (4)0.7881 (4)0.48237 (16)0.0230 (5)
H260.76810.79900.54270.028*
C270.8098 (5)0.8098 (5)0.13936 (18)0.0341 (7)
H27A0.72780.67080.13360.051*
H27B0.90340.84060.09040.051*
H27C0.71500.89510.13690.051*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0311 (4)0.0328 (4)0.0258 (4)0.0106 (3)0.0068 (3)0.0035 (3)
O10.0208 (9)0.0398 (12)0.0308 (10)0.0057 (9)0.0011 (7)0.0014 (9)
O20.0240 (10)0.0397 (12)0.0398 (12)0.0089 (9)0.0092 (8)0.0023 (10)
C10.0224 (12)0.0179 (12)0.0263 (12)0.0073 (10)0.0011 (9)0.0008 (10)
C20.0224 (12)0.0213 (12)0.0269 (12)0.0049 (10)0.0007 (10)0.0013 (10)
C30.0236 (12)0.0192 (12)0.0263 (12)0.0059 (10)0.0013 (9)0.0020 (10)
C110.0250 (12)0.0190 (12)0.0253 (12)0.0089 (10)0.0034 (10)0.0000 (9)
C120.0286 (13)0.0189 (12)0.0313 (13)0.0087 (10)0.0077 (10)0.0005 (10)
C130.0447 (17)0.0290 (14)0.0308 (14)0.0150 (13)0.0143 (12)0.0051 (11)
C140.0540 (19)0.0390 (17)0.0257 (13)0.0191 (15)0.0024 (13)0.0009 (12)
C150.0376 (16)0.0471 (18)0.0293 (14)0.0152 (14)0.0056 (12)0.0035 (13)
C160.0274 (13)0.0353 (15)0.0280 (13)0.0122 (12)0.0015 (10)0.0026 (11)
C210.0246 (12)0.0169 (11)0.0230 (12)0.0055 (10)0.0008 (9)0.0000 (9)
C220.0219 (12)0.0255 (13)0.0255 (12)0.0055 (10)0.0052 (9)0.0012 (10)
C230.0286 (13)0.0258 (13)0.0199 (11)0.0076 (11)0.0037 (9)0.0019 (10)
C240.0265 (12)0.0184 (12)0.0210 (11)0.0068 (10)0.0014 (9)0.0001 (9)
C250.0207 (11)0.0217 (12)0.0252 (12)0.0036 (10)0.0034 (9)0.0013 (10)
C260.0259 (13)0.0220 (12)0.0200 (11)0.0055 (10)0.0033 (9)0.0013 (9)
C270.0504 (18)0.0318 (15)0.0235 (13)0.0164 (14)0.0050 (12)0.0014 (11)
Geometric parameters (Å, º) top
S1—C241.765 (3)C14—H140.9500
S1—C271.806 (3)C15—C161.391 (4)
O1—C11.250 (3)C15—H150.9500
O2—C121.351 (3)C16—H160.9500
O2—H2O0.83 (5)C21—C221.402 (3)
C1—C21.472 (3)C21—C261.406 (3)
C1—C111.489 (3)C22—C231.394 (4)
C2—C31.347 (4)C22—H220.9500
C2—H20.9500C23—C241.400 (4)
C3—C211.461 (3)C23—H230.9500
C3—H30.9500C24—C251.412 (3)
C11—C161.403 (4)C25—C261.385 (4)
C11—C121.423 (4)C25—H250.9500
C12—C131.399 (4)C26—H260.9500
C13—C141.382 (5)C27—H27A0.9800
C13—H130.9500C27—H27B0.9800
C14—C151.391 (5)C27—H27C0.9800
C24—S1—C27103.57 (13)C15—C16—H16119.3
C12—O2—H2O107 (4)C11—C16—H16119.3
O1—C1—C2119.9 (2)C22—C21—C26118.0 (2)
O1—C1—C11119.5 (2)C22—C21—C3118.6 (2)
C2—C1—C11120.7 (2)C26—C21—C3123.4 (2)
C3—C2—C1120.0 (2)C23—C22—C21121.7 (2)
C3—C2—H2120.0C23—C22—H22119.1
C1—C2—H2120.0C21—C22—H22119.1
C2—C3—C21127.6 (2)C22—C23—C24119.7 (2)
C2—C3—H3116.2C22—C23—H23120.1
C21—C3—H3116.2C24—C23—H23120.1
C16—C11—C12118.0 (2)C23—C24—C25119.1 (2)
C16—C11—C1122.8 (2)C23—C24—S1125.08 (19)
C12—C11—C1119.2 (2)C25—C24—S1115.84 (19)
O2—C12—C13117.8 (2)C26—C25—C24120.5 (2)
O2—C12—C11122.3 (2)C26—C25—H25119.8
C13—C12—C11119.9 (3)C24—C25—H25119.8
C14—C13—C12120.7 (3)C25—C26—C21121.0 (2)
C14—C13—H13119.7C25—C26—H26119.5
C12—C13—H13119.7C21—C26—H26119.5
C13—C14—C15120.3 (3)S1—C27—H27A109.5
C13—C14—H14119.9S1—C27—H27B109.5
C15—C14—H14119.9H27A—C27—H27B109.5
C16—C15—C14119.8 (3)S1—C27—H27C109.5
C16—C15—H15120.1H27A—C27—H27C109.5
C14—C15—H15120.1H27B—C27—H27C109.5
C15—C16—C11121.4 (3)
O1—C1—C2—C34.6 (4)C12—C11—C16—C150.5 (4)
C11—C1—C2—C3175.6 (2)C1—C11—C16—C15179.2 (3)
C1—C2—C3—C21179.4 (2)C2—C3—C21—C22173.2 (3)
O1—C1—C11—C16178.8 (3)C2—C3—C21—C267.1 (4)
C2—C1—C11—C161.4 (4)C26—C21—C22—C231.0 (4)
O1—C1—C11—C120.1 (4)C3—C21—C22—C23179.2 (2)
C2—C1—C11—C12179.9 (2)C21—C22—C23—C240.2 (4)
C16—C11—C12—O2178.5 (2)C22—C23—C24—C250.5 (4)
C1—C11—C12—O20.2 (4)C22—C23—C24—S1179.7 (2)
C16—C11—C12—C131.5 (4)C27—S1—C24—C231.5 (3)
C1—C11—C12—C13179.7 (2)C27—S1—C24—C25178.3 (2)
O2—C12—C13—C14178.3 (3)C23—C24—C25—C260.3 (4)
C11—C12—C13—C141.8 (4)S1—C24—C25—C26179.9 (2)
C12—C13—C14—C150.9 (5)C24—C25—C26—C210.5 (4)
C13—C14—C15—C160.2 (5)C22—C21—C26—C251.2 (4)
C14—C15—C16—C110.3 (5)C3—C21—C26—C25179.1 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H2O···O10.83 (5)1.78 (5)2.536 (3)150 (5)

Experimental details

Crystal data
Chemical formulaC16H14O2S
Mr270.33
Crystal system, space groupTriclinic, P1
Temperature (K)173
a, b, c (Å)6.6516 (9), 7.0223 (11), 15.0248 (17)
α, β, γ (°)90.789 (11), 93.409 (11), 105.718 (12)
V3)673.98 (16)
Z2
Radiation typeMo Kα
µ (mm1)0.23
Crystal size (mm)0.37 × 0.31 × 0.12
Data collection
DiffractometerStoe IPDSII two-circle
Absorption correctionMulti-scan
(MULABS; Spek, 2003; Blessing, 1995)
Tmin, Tmax0.938, 0.982
No. of measured, independent and
observed [I > 2σ(I)] reflections
13663, 2807, 2451
Rint0.077
(sin θ/λ)max1)0.631
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.057, 0.184, 1.10
No. of reflections2807
No. of parameters179
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.59, 0.43

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
O2—H2O···O10.83 (5)1.78 (5)2.536 (3)150 (5)
 

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