Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807052312/at2443sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807052312/at2443Isup2.hkl |
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
checkCIF/PLATON results
No syntax errors found No errors found in this datablock
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).
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%).
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).
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).
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).
Fig. 1. Perspective view of the title compound with the atom numbering; displacement ellipsoids are at the 50% probability level. | |
Fig. 2. The formation of the title compound. |
C16H14O2S | Z = 2 |
Mr = 270.33 | F(000) = 284 |
Triclinic, P1 | Dx = 1.332 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 6.6516 (9) Å | Cell parameters from 5613 reflections |
b = 7.0223 (11) Å | θ = 3.7–26.1° |
c = 15.0248 (17) Å | µ = 0.23 mm−1 |
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 |
Stoe IPDSII two-circle diffractometer | 2807 independent reflections |
Radiation source: fine-focus sealed tube | 2451 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.077 |
ω scans | θmax = 26.6°, θmin = 3.6° |
Absorption correction: multi-scan (MULABS; Spek, 2003; Blessing, 1995) | h = −8→8 |
Tmin = 0.938, Tmax = 0.982 | k = −8→8 |
13663 measured reflections | l = −18→18 |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.057 | H 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 reflections | Δρmax = 0.59 e Å−3 |
179 parameters | Δρmin = −0.43 e Å−3 |
0 restraints | Extinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.056 (11) |
C16H14O2S | γ = 105.718 (12)° |
Mr = 270.33 | V = 673.98 (16) Å3 |
Triclinic, P1 | Z = 2 |
a = 6.6516 (9) Å | Mo Kα radiation |
b = 7.0223 (11) Å | µ = 0.23 mm−1 |
c = 15.0248 (17) Å | T = 173 K |
α = 90.789 (11)° | 0.37 × 0.31 × 0.12 mm |
β = 93.409 (11)° |
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 = 0.982 | Rint = 0.077 |
13663 measured reflections |
R[F2 > 2σ(F2)] = 0.057 | 0 restraints |
wR(F2) = 0.184 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.10 | Δρmax = 0.59 e Å−3 |
2807 reflections | Δρmin = −0.43 e Å−3 |
179 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
S1 | 0.96299 (11) | 0.85185 (11) | 0.24466 (4) | 0.0293 (3) | |
O1 | 0.0262 (3) | 0.6428 (3) | 0.64803 (13) | 0.0311 (5) | |
O2 | −0.1191 (3) | 0.6145 (3) | 0.80106 (15) | 0.0341 (5) | |
H2O | −0.117 (8) | 0.615 (8) | 0.746 (3) | 0.072 (15)* | |
C1 | 0.2112 (4) | 0.6915 (4) | 0.68040 (17) | 0.0219 (5) | |
C2 | 0.3848 (4) | 0.7324 (4) | 0.62090 (17) | 0.0238 (5) | |
H2 | 0.5252 | 0.7788 | 0.6452 | 0.029* | |
C3 | 0.3447 (4) | 0.7040 (4) | 0.53205 (17) | 0.0230 (5) | |
H3 | 0.2015 | 0.6561 | 0.5117 | 0.028* | |
C11 | 0.2534 (4) | 0.7082 (4) | 0.77907 (17) | 0.0224 (5) | |
C12 | 0.0818 (4) | 0.6681 (4) | 0.83462 (18) | 0.0256 (6) | |
C13 | 0.1188 (5) | 0.6841 (4) | 0.92739 (19) | 0.0334 (7) | |
H13 | 0.0040 | 0.6608 | 0.9643 | 0.040* | |
C14 | 0.3208 (6) | 0.7333 (5) | 0.96593 (19) | 0.0383 (7) | |
H14 | 0.3438 | 0.7419 | 1.0290 | 0.046* | |
C15 | 0.4904 (5) | 0.7705 (5) | 0.91268 (19) | 0.0377 (7) | |
H15 | 0.6291 | 0.8040 | 0.9393 | 0.045* | |
C16 | 0.4565 (4) | 0.7584 (4) | 0.82031 (18) | 0.0296 (6) | |
H16 | 0.5731 | 0.7847 | 0.7844 | 0.036* | |
C21 | 0.4959 (4) | 0.7383 (4) | 0.46331 (16) | 0.0216 (5) | |
C22 | 0.4208 (4) | 0.7199 (4) | 0.37357 (17) | 0.0247 (5) | |
H22 | 0.2739 | 0.6841 | 0.3594 | 0.030* | |
C23 | 0.5558 (4) | 0.7527 (4) | 0.30451 (16) | 0.0249 (5) | |
H23 | 0.5011 | 0.7397 | 0.2442 | 0.030* | |
C24 | 0.7725 (4) | 0.8047 (4) | 0.32437 (16) | 0.0218 (5) | |
C25 | 0.8500 (4) | 0.8217 (4) | 0.41452 (17) | 0.0231 (5) | |
H25 | 0.9967 | 0.8564 | 0.4287 | 0.028* | |
C26 | 0.7137 (4) | 0.7881 (4) | 0.48237 (16) | 0.0230 (5) | |
H26 | 0.7681 | 0.7990 | 0.5427 | 0.028* | |
C27 | 0.8098 (5) | 0.8098 (5) | 0.13936 (18) | 0.0341 (7) | |
H27A | 0.7278 | 0.6708 | 0.1336 | 0.051* | |
H27B | 0.9034 | 0.8406 | 0.0904 | 0.051* | |
H27C | 0.7150 | 0.8951 | 0.1369 | 0.051* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0311 (4) | 0.0328 (4) | 0.0258 (4) | 0.0106 (3) | 0.0068 (3) | 0.0035 (3) |
O1 | 0.0208 (9) | 0.0398 (12) | 0.0308 (10) | 0.0057 (9) | −0.0011 (7) | 0.0014 (9) |
O2 | 0.0240 (10) | 0.0397 (12) | 0.0398 (12) | 0.0089 (9) | 0.0092 (8) | 0.0023 (10) |
C1 | 0.0224 (12) | 0.0179 (12) | 0.0263 (12) | 0.0073 (10) | 0.0011 (9) | 0.0008 (10) |
C2 | 0.0224 (12) | 0.0213 (12) | 0.0269 (12) | 0.0049 (10) | 0.0007 (10) | −0.0013 (10) |
C3 | 0.0236 (12) | 0.0192 (12) | 0.0263 (12) | 0.0059 (10) | 0.0013 (9) | 0.0020 (10) |
C11 | 0.0250 (12) | 0.0190 (12) | 0.0253 (12) | 0.0089 (10) | 0.0034 (10) | 0.0000 (9) |
C12 | 0.0286 (13) | 0.0189 (12) | 0.0313 (13) | 0.0087 (10) | 0.0077 (10) | 0.0005 (10) |
C13 | 0.0447 (17) | 0.0290 (14) | 0.0308 (14) | 0.0150 (13) | 0.0143 (12) | 0.0051 (11) |
C14 | 0.0540 (19) | 0.0390 (17) | 0.0257 (13) | 0.0191 (15) | 0.0024 (13) | 0.0009 (12) |
C15 | 0.0376 (16) | 0.0471 (18) | 0.0293 (14) | 0.0152 (14) | −0.0056 (12) | −0.0035 (13) |
C16 | 0.0274 (13) | 0.0353 (15) | 0.0280 (13) | 0.0122 (12) | 0.0015 (10) | −0.0026 (11) |
C21 | 0.0246 (12) | 0.0169 (11) | 0.0230 (12) | 0.0055 (10) | −0.0008 (9) | 0.0000 (9) |
C22 | 0.0219 (12) | 0.0255 (13) | 0.0255 (12) | 0.0055 (10) | −0.0052 (9) | −0.0012 (10) |
C23 | 0.0286 (13) | 0.0258 (13) | 0.0199 (11) | 0.0076 (11) | −0.0037 (9) | −0.0019 (10) |
C24 | 0.0265 (12) | 0.0184 (12) | 0.0210 (11) | 0.0068 (10) | 0.0014 (9) | 0.0001 (9) |
C25 | 0.0207 (11) | 0.0217 (12) | 0.0252 (12) | 0.0036 (10) | −0.0034 (9) | −0.0013 (10) |
C26 | 0.0259 (13) | 0.0220 (12) | 0.0200 (11) | 0.0055 (10) | −0.0033 (9) | −0.0013 (9) |
C27 | 0.0504 (18) | 0.0318 (15) | 0.0235 (13) | 0.0164 (14) | 0.0050 (12) | 0.0014 (11) |
S1—C24 | 1.765 (3) | C14—H14 | 0.9500 |
S1—C27 | 1.806 (3) | C15—C16 | 1.391 (4) |
O1—C1 | 1.250 (3) | C15—H15 | 0.9500 |
O2—C12 | 1.351 (3) | C16—H16 | 0.9500 |
O2—H2O | 0.83 (5) | C21—C22 | 1.402 (3) |
C1—C2 | 1.472 (3) | C21—C26 | 1.406 (3) |
C1—C11 | 1.489 (3) | C22—C23 | 1.394 (4) |
C2—C3 | 1.347 (4) | C22—H22 | 0.9500 |
C2—H2 | 0.9500 | C23—C24 | 1.400 (4) |
C3—C21 | 1.461 (3) | C23—H23 | 0.9500 |
C3—H3 | 0.9500 | C24—C25 | 1.412 (3) |
C11—C16 | 1.403 (4) | C25—C26 | 1.385 (4) |
C11—C12 | 1.423 (4) | C25—H25 | 0.9500 |
C12—C13 | 1.399 (4) | C26—H26 | 0.9500 |
C13—C14 | 1.382 (5) | C27—H27A | 0.9800 |
C13—H13 | 0.9500 | C27—H27B | 0.9800 |
C14—C15 | 1.391 (5) | C27—H27C | 0.9800 |
C24—S1—C27 | 103.57 (13) | C15—C16—H16 | 119.3 |
C12—O2—H2O | 107 (4) | C11—C16—H16 | 119.3 |
O1—C1—C2 | 119.9 (2) | C22—C21—C26 | 118.0 (2) |
O1—C1—C11 | 119.5 (2) | C22—C21—C3 | 118.6 (2) |
C2—C1—C11 | 120.7 (2) | C26—C21—C3 | 123.4 (2) |
C3—C2—C1 | 120.0 (2) | C23—C22—C21 | 121.7 (2) |
C3—C2—H2 | 120.0 | C23—C22—H22 | 119.1 |
C1—C2—H2 | 120.0 | C21—C22—H22 | 119.1 |
C2—C3—C21 | 127.6 (2) | C22—C23—C24 | 119.7 (2) |
C2—C3—H3 | 116.2 | C22—C23—H23 | 120.1 |
C21—C3—H3 | 116.2 | C24—C23—H23 | 120.1 |
C16—C11—C12 | 118.0 (2) | C23—C24—C25 | 119.1 (2) |
C16—C11—C1 | 122.8 (2) | C23—C24—S1 | 125.08 (19) |
C12—C11—C1 | 119.2 (2) | C25—C24—S1 | 115.84 (19) |
O2—C12—C13 | 117.8 (2) | C26—C25—C24 | 120.5 (2) |
O2—C12—C11 | 122.3 (2) | C26—C25—H25 | 119.8 |
C13—C12—C11 | 119.9 (3) | C24—C25—H25 | 119.8 |
C14—C13—C12 | 120.7 (3) | C25—C26—C21 | 121.0 (2) |
C14—C13—H13 | 119.7 | C25—C26—H26 | 119.5 |
C12—C13—H13 | 119.7 | C21—C26—H26 | 119.5 |
C13—C14—C15 | 120.3 (3) | S1—C27—H27A | 109.5 |
C13—C14—H14 | 119.9 | S1—C27—H27B | 109.5 |
C15—C14—H14 | 119.9 | H27A—C27—H27B | 109.5 |
C16—C15—C14 | 119.8 (3) | S1—C27—H27C | 109.5 |
C16—C15—H15 | 120.1 | H27A—C27—H27C | 109.5 |
C14—C15—H15 | 120.1 | H27B—C27—H27C | 109.5 |
C15—C16—C11 | 121.4 (3) | ||
O1—C1—C2—C3 | −4.6 (4) | C12—C11—C16—C15 | −0.5 (4) |
C11—C1—C2—C3 | 175.6 (2) | C1—C11—C16—C15 | −179.2 (3) |
C1—C2—C3—C21 | 179.4 (2) | C2—C3—C21—C22 | −173.2 (3) |
O1—C1—C11—C16 | 178.8 (3) | C2—C3—C21—C26 | 7.1 (4) |
C2—C1—C11—C16 | −1.4 (4) | C26—C21—C22—C23 | −1.0 (4) |
O1—C1—C11—C12 | 0.1 (4) | C3—C21—C22—C23 | 179.2 (2) |
C2—C1—C11—C12 | 179.9 (2) | C21—C22—C23—C24 | 0.2 (4) |
C16—C11—C12—O2 | −178.5 (2) | C22—C23—C24—C25 | 0.5 (4) |
C1—C11—C12—O2 | 0.2 (4) | C22—C23—C24—S1 | −179.7 (2) |
C16—C11—C12—C13 | 1.5 (4) | C27—S1—C24—C23 | −1.5 (3) |
C1—C11—C12—C13 | −179.7 (2) | C27—S1—C24—C25 | 178.3 (2) |
O2—C12—C13—C14 | 178.3 (3) | C23—C24—C25—C26 | −0.3 (4) |
C11—C12—C13—C14 | −1.8 (4) | S1—C24—C25—C26 | 179.9 (2) |
C12—C13—C14—C15 | 0.9 (5) | C24—C25—C26—C21 | −0.5 (4) |
C13—C14—C15—C16 | 0.2 (5) | C22—C21—C26—C25 | 1.2 (4) |
C14—C15—C16—C11 | −0.3 (5) | C3—C21—C26—C25 | −179.1 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H2O···O1 | 0.83 (5) | 1.78 (5) | 2.536 (3) | 150 (5) |
Experimental details
Crystal data | |
Chemical formula | C16H14O2S |
Mr | 270.33 |
Crystal system, space group | Triclinic, 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) |
V (Å3) | 673.98 (16) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.23 |
Crystal size (mm) | 0.37 × 0.31 × 0.12 |
Data collection | |
Diffractometer | Stoe IPDSII two-circle |
Absorption correction | Multi-scan (MULABS; Spek, 2003; Blessing, 1995) |
Tmin, Tmax | 0.938, 0.982 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 13663, 2807, 2451 |
Rint | 0.077 |
(sin θ/λ)max (Å−1) | 0.631 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.057, 0.184, 1.10 |
No. of reflections | 2807 |
No. of parameters | 179 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.59, −0.43 |
Computer programs: X-AREA (Stoe & Cie, 2001), SHELXS97 (Sheldrick, 1990), SHELXL97 (Sheldrick, 1997), XP in SHELXTL-Plus (Sheldrick, 1991).
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H2O···O1 | 0.83 (5) | 1.78 (5) | 2.536 (3) | 150 (5) |
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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).