(2E)-3-(4-Chloro­phen­yl)-1-[4-(methyl­sulfan­yl)phen­yl]prop-2-en-1-one

In the title mol­ecule, C₁₆H₁₃ClOS, the dihedral angle between the two benzene rings is 51.0 (1)°.

Key indicators

• Single-crystal X-ray study
• T = 200 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.035
• wR factor = 0.077
• Data-to-parameter ratio = 26.0

checkCIF/PLATON results

No syntax errors found



Alert level C
ABSTM02_ALERT_3_C  The ratio of expected to reported Tmax/Tmin(RR') is < 0.90
            Tmin and Tmax reported:      0.829     1.000
            Tmin(prime) and Tmax expected:      0.819     0.884
            RR(prime) =      0.895
            Please check that your absorption correction is appropriate.
PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large .............       0.89
PLAT062_ALERT_4_C Rescale T(min) & T(max) by .....................       0.88

Alert level G
ABSTM02_ALERT_3_G  When printed, the submitted absorption T values will be
            replaced by the scaled T values. Since the ratio of scaled T's
            is identical to the ratio of reported T values, the scaling
            does not imply a change to the absorption corrections used in
            the study.
            Ratio of Tmax expected/reported      0.884
            Tmax scaled      0.884 Tmin scaled      0.733

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   3 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   3 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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S1. Comment

Many patents have appeared in literature describing the usefulness of Chalcones and their derivatives. Their diverse applications such as artificial sweeteners, stabilizers against heat and visible light, color photography, scintillators, polymerization catalysts, fluorescent lightning agents and as brightening agents are well studied and documented (Dhar, 1981). The title material is used as an intermediate to prepare the corresponding pyrazole derivatives which have shown better antiinflamatory and analgesic activities. In the title molecule, C₁₆H₁₃ClOS, Fig.1, the dihedral angle between the two phenyl rings is 51.0 (1)°. The presence of a methylsulfanylphenyl group in the title molecule causes the 4-chlorophenyl group to twist away from each other. There are no classical hydrogen bonds found in the structure. In similar structures like 4,4'-Dimethylchalcone (Rabinovich & Shakked, 1974), 2',6'-Dihydroxy-4,4'-dimethoxychalcone (Schmalle et al., 1990) and 1-(4-Chlorophenyl)-3-(4-hydroxyphenyl) prop-2-en-1-one(Ravishankar et al., 2005), the dihedral angle between the two phenyl rings are 48.6°, 13.1 (4)° and 26.1 (1)° respectively.

Related literature

For the uses of chalcones, see: Dhar (1981). For related crystal structures, see: Rabinovich & Shakked (1974); Ravishankar et al. (2005); Schmalle et al. (1990).

S2. Experimental

4-Chlororobenzaldehyde (2.5 g, 0.02 mol) in ethanol is mixed with 4-methylthio acetophenone (2.80 g, 0.02 mol) in 50 ml e thanol and the mixture was treated with 10 ml of 10% NaOH solution at 283 K and stirred for 8 h. The precipitate obtained was filtered, washed with ethanol and dried. Pale yellow rods of the title compound were grown from toluene by slow evaporation. The yield of the isolated product was 3.5 g (60%)

S3. Refinement

H atoms were positioned geometrically and allowed to ride on their parent atoms, with C—H = 0.95–0.98 Å and U_iso=1.2 to 1.5 times U_eq(C).

Computing details

Data collection: CrysAlis CCD (Oxford Diffraction, 2007); cell refinement: CrysAlis CCD (Oxford Diffraction, 2007); data reduction: CrysAlis RED (Oxford Diffraction, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: PLATON (Spek, 2003).

Figures

Fig. 1. The molecular structure of the title compound with the atomic numbering and 50% probability displacement ellipsoids. H atoms are shown shown as small spheres of arbitrary radius.

(2E)-3-(4-Chlorophenyl)-1-[4-(methylsulfanyl)phenyl]prop-2-en-1-one

Crystal data

C16H13ClOS	F(000) = 600
Mr = 288.78	Dx = 1.418 Mg m^−3
Monoclinic, P21/c	Melting point: 444(1) K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 16.515 (1) Å	Cell parameters from 4494 reflections
b = 14.3026 (9) Å	θ = 4.5–32.6°
c = 5.7280 (3) Å	µ = 0.42 mm^−1
β = 91.284 (5)°	T = 200 K
V = 1352.66 (14) Å^3	Prism, colourless
Z = 4	0.46 × 0.37 × 0.29 mm

Data collection

Oxford Diffraction Gemini diffractometer	4494 independent reflections
Radiation source: fine-focus sealed tube	2386 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.038
Detector resolution: 10.5081 pixels mm^-1	θmax = 32.6°, θmin = 4.5°
ϕ and ω scans	h = −24→22
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007)	k = −21→21
Tmin = 0.829, Tmax = 1.000	l = −8→7
12209 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.077	H-atom parameters constrained
S = 0.86	w = 1/[σ^2(Fo^2) + (0.0355P)^2] where P = (Fo^2 + 2Fc^2)/3
4494 reflections	(Δ/σ)max < 0.001
173 parameters	Δρmax = 0.28 e Å^−3
0 restraints	Δρmin = −0.23 e Å^−3

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 (Ų)

	x	y	z	Uiso*/Ueq
Cl4	0.97354 (2)	0.13561 (3)	−0.14833 (6)	0.0456 (1)
S4	0.18062 (2)	0.10519 (3)	0.17298 (6)	0.0317 (1)
O1	0.54563 (6)	0.14122 (7)	0.71632 (15)	0.0382 (3)
C1	0.52954 (8)	0.13336 (9)	0.5078 (2)	0.0266 (4)
C2	0.59470 (8)	0.13108 (9)	0.3341 (2)	0.0276 (4)
C3	0.66980 (8)	0.10839 (9)	0.3972 (2)	0.0245 (4)
C4	0.12122 (9)	0.15828 (11)	0.3950 (3)	0.0417 (5)
C11	0.74201 (8)	0.11142 (8)	0.2543 (2)	0.0225 (4)
C12	0.81511 (8)	0.07634 (9)	0.3441 (2)	0.0264 (4)
C13	0.88615 (8)	0.08273 (9)	0.2223 (2)	0.0293 (4)
C14	0.88454 (8)	0.12614 (9)	0.0085 (2)	0.0269 (4)
C15	0.81354 (8)	0.16220 (9)	−0.0877 (2)	0.0263 (4)
C16	0.74260 (8)	0.15401 (8)	0.0342 (2)	0.0246 (4)
C21	0.44370 (8)	0.12768 (8)	0.4239 (2)	0.0232 (4)
C22	0.38269 (8)	0.15922 (8)	0.5672 (2)	0.0255 (4)
C23	0.30208 (8)	0.15462 (8)	0.4988 (2)	0.0264 (4)
C24	0.28069 (8)	0.11603 (8)	0.2817 (2)	0.0230 (4)
C25	0.34163 (8)	0.08362 (9)	0.1382 (2)	0.0264 (4)
C26	0.42171 (8)	0.09072 (9)	0.2052 (2)	0.0274 (4)
H2	0.58245	0.14608	0.17562	0.0331*
H3	0.67768	0.08772	0.55367	0.0294*
H4A	0.06385	0.15646	0.34764	0.0626*
H4B	0.12909	0.12401	0.54194	0.0626*
H4C	0.13824	0.22339	0.41688	0.0626*
H12	0.81606	0.04723	0.49317	0.0317*
H13	0.93518	0.05757	0.28528	0.0351*
H15	0.81356	0.19222	−0.23563	0.0315*
H16	0.69352	0.17762	−0.03236	0.0296*
H22	0.39678	0.18459	0.71588	0.0306*
H23	0.26141	0.17753	0.59856	0.0317*
H25	0.32756	0.05620	−0.00824	0.0316*
H26	0.46250	0.07040	0.10248	0.0328*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl4	0.0292 (2)	0.0657 (3)	0.0423 (2)	−0.0028 (2)	0.0115 (2)	0.0008 (2)
S4	0.0282 (2)	0.0334 (2)	0.0331 (2)	−0.0029 (2)	−0.0041 (1)	−0.0008 (2)
O1	0.0310 (6)	0.0587 (7)	0.0249 (5)	0.0038 (5)	−0.0013 (4)	−0.0022 (4)
C1	0.0282 (8)	0.0263 (7)	0.0253 (7)	0.0026 (6)	0.0019 (5)	0.0014 (6)
C2	0.0268 (7)	0.0326 (7)	0.0235 (7)	−0.0006 (6)	0.0012 (5)	0.0019 (6)
C3	0.0275 (7)	0.0243 (7)	0.0218 (6)	−0.0005 (6)	0.0023 (5)	0.0002 (5)
C4	0.0252 (8)	0.0474 (9)	0.0526 (9)	0.0041 (7)	0.0014 (6)	−0.0073 (7)
C11	0.0247 (7)	0.0201 (6)	0.0225 (6)	−0.0015 (5)	−0.0011 (5)	−0.0026 (5)
C12	0.0296 (7)	0.0263 (7)	0.0232 (6)	0.0014 (6)	−0.0024 (5)	0.0017 (5)
C13	0.0242 (7)	0.0339 (8)	0.0295 (7)	0.0033 (6)	−0.0031 (5)	−0.0013 (6)
C14	0.0244 (7)	0.0282 (7)	0.0282 (7)	−0.0042 (6)	0.0041 (5)	−0.0060 (6)
C15	0.0316 (8)	0.0267 (7)	0.0205 (6)	−0.0014 (6)	0.0008 (5)	0.0002 (5)
C16	0.0242 (7)	0.0262 (7)	0.0234 (7)	0.0018 (6)	−0.0023 (5)	−0.0020 (5)
C21	0.0243 (7)	0.0220 (7)	0.0235 (6)	0.0003 (5)	0.0043 (5)	0.0020 (5)
C22	0.0287 (7)	0.0274 (7)	0.0204 (6)	−0.0009 (6)	0.0011 (5)	−0.0008 (5)
C23	0.0260 (7)	0.0275 (7)	0.0260 (7)	0.0011 (6)	0.0060 (5)	−0.0016 (5)
C24	0.0267 (7)	0.0188 (6)	0.0236 (6)	−0.0023 (5)	−0.0002 (5)	0.0035 (5)
C25	0.0316 (8)	0.0271 (7)	0.0204 (6)	−0.0031 (6)	0.0016 (5)	−0.0015 (5)
C26	0.0300 (8)	0.0279 (7)	0.0245 (7)	0.0011 (6)	0.0085 (5)	−0.0009 (6)

Geometric parameters (Å, º)

Cl4—C14	1.7450 (13)	C23—C24	1.3986 (16)
S4—C4	1.7922 (17)	C24—C25	1.3930 (18)
S4—C24	1.7598 (13)	C25—C26	1.3726 (19)
O1—C1	1.2230 (14)	C2—H2	0.9500
C1—C2	1.4822 (18)	C3—H3	0.9500
C1—C21	1.4889 (18)	C4—H4A	0.9800
C2—C3	1.3244 (19)	C4—H4B	0.9800
C3—C11	1.4621 (18)	C4—H4C	0.9800
C11—C12	1.3950 (18)	C12—H12	0.9500
C11—C16	1.4004 (16)	C13—H13	0.9500
C12—C13	1.3814 (18)	C15—H15	0.9500
C13—C14	1.3728 (17)	C16—H16	0.9500
C14—C15	1.3841 (18)	C22—H22	0.9500
C15—C16	1.3822 (18)	C23—H23	0.9500
C21—C22	1.3891 (18)	C25—H25	0.9500
C21—C26	1.4001 (17)	C26—H26	0.9500
C22—C23	1.3809 (19)
C4—S4—C24	103.66 (7)	C1—C2—H2	120.00
O1—C1—C2	120.83 (12)	C3—C2—H2	120.00
O1—C1—C21	120.31 (11)	C2—C3—H3	116.00
C2—C1—C21	118.85 (10)	C11—C3—H3	116.00
C1—C2—C3	120.78 (11)	S4—C4—H4A	109.00
C2—C3—C11	127.63 (11)	S4—C4—H4B	109.00
C3—C11—C12	119.53 (11)	S4—C4—H4C	109.00
C3—C11—C16	122.62 (11)	H4A—C4—H4B	109.00
C12—C11—C16	117.71 (12)	H4A—C4—H4C	109.00
C11—C12—C13	121.86 (11)	H4B—C4—H4C	109.00
C12—C13—C14	118.74 (12)	C11—C12—H12	119.00
Cl4—C14—C13	119.65 (10)	C13—C12—H12	119.00
Cl4—C14—C15	118.82 (9)	C12—C13—H13	121.00
C13—C14—C15	121.53 (12)	C14—C13—H13	121.00
C14—C15—C16	119.17 (11)	C14—C15—H15	120.00
C11—C16—C15	120.98 (12)	C16—C15—H15	120.00
C1—C21—C22	119.31 (10)	C11—C16—H16	120.00
C1—C21—C26	122.37 (11)	C15—C16—H16	119.00
C22—C21—C26	118.31 (12)	C21—C22—H22	119.00
C21—C22—C23	121.62 (11)	C23—C22—H22	119.00
C22—C23—C24	119.59 (11)	C22—C23—H23	120.00
S4—C24—C23	124.46 (10)	C24—C23—H23	120.00
S4—C24—C25	116.56 (9)	C24—C25—H25	120.00
C23—C24—C25	118.98 (12)	C26—C25—H25	120.00
C24—C25—C26	120.98 (11)	C21—C26—H26	120.00
C21—C26—C25	120.47 (12)	C25—C26—H26	120.00
C4—S4—C24—C23	2.51 (12)	C12—C13—C14—C15	−0.84 (19)
C4—S4—C24—C25	−177.35 (10)	C12—C13—C14—Cl4	179.71 (10)
O1—C1—C2—C3	21.2 (2)	Cl4—C14—C15—C16	179.25 (10)
O1—C1—C21—C26	−159.89 (12)	C13—C14—C15—C16	−0.20 (19)
C21—C1—C2—C3	−159.94 (12)	C14—C15—C16—C11	1.15 (18)
O1—C1—C21—C22	19.52 (18)	C1—C21—C26—C25	177.59 (12)
C2—C1—C21—C26	21.23 (18)	C22—C21—C26—C25	−1.83 (18)
C2—C1—C21—C22	−159.36 (11)	C1—C21—C22—C23	−179.31 (11)
C1—C2—C3—C11	−173.63 (12)	C26—C21—C22—C23	0.13 (18)
C2—C3—C11—C12	−173.92 (13)	C21—C22—C23—C24	1.01 (17)
C2—C3—C11—C16	10.4 (2)	C22—C23—C24—C25	−0.47 (17)
C16—C11—C12—C13	−0.07 (18)	C22—C23—C24—S4	179.67 (9)
C3—C11—C12—C13	−175.92 (12)	S4—C24—C25—C26	178.65 (10)
C12—C11—C16—C15	−1.01 (17)	C23—C24—C25—C26	−1.23 (18)
C3—C11—C16—C15	174.71 (12)	C24—C25—C26—C21	2.40 (19)
C11—C12—C13—C14	0.98 (19)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C15—H15···Cg^i	0.95	2.81	3.527 (1)	133
C22—H22···Cg^ii	0.95	2.94	3.550 (1)	124

Symmetry codes: (i) x, −y+1/2, z−1/2; (ii) x, −y+1/2, z+1/2.