(E)-3-(4-Fluoro-phen-yl)-1-[4-(methyl-sulfan-yl)phen-yl]prop-2-en-1-one.

In the title mol-ecule, C(16)H(13)FOS, the dihedral angle between the two benzene rings is 8.68 (6)°. The H atoms of the central enone group are trans and one H atom is involved in a close intra-molecular C-H⋯O contact. The crystal structure is stabilized by weak C-H⋯π inter-actions.

Related literature

For related crystal structures, see: Moorthi et al. (2005 ▶); Sathiya Moorthi, et al. (2005 ▶); Thiruvalluvar, Subramanyam, Butcher, Adhikari & Wagle (2007 ▶); Thiruvalluvar, Subramanyam, Butcher, Adhikari & Karabasanagouda (2007 ▶); Thiruvalluvar, Subramanyam, Butcher, Karegoudar & Holla (2008 ▶); Thiruvalluvar, Subramanyam, Butcher, Karabasanagouda & Adhikari (2008 ▶). For biological activities of chalcones, see: Anto et al. (1995 ▶); Vaya et al. (1997 ▶); Mukherjee et al. (2001 ▶); Indyah et al. (2000 ▶); Chen et al. (1997 ▶); Nielsen et al. (1998 ▶); Hsin et al. (1998 ▶); Kumar et al. (2003 ▶); Prasad et al. (2005 ▶).

Experimental

Crystal data

C16H13FOS

M = 272.33

Monoclinic,

a = 29.7846 (9) Å

b = 5.7070 (3) Å

c = 7.7071 (4) Å

β = 90.781 (3)°

V = 1309.94 (10) Å3

Z = 4

Mo Kα radiation

μ = 0.25 mm−1

T = 200 (2) K

0.44 × 0.41 × 0.31 mm

Data collection

Oxford Diffraction R Gemini diffractometer

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2008 ▶) T min = 0.945, T max = 1.000 (expected range = 0.876–0.926)

11708 measured reflections

4318 independent reflections

2944 reflections with I > 2σ(I)

R int = 0.024

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.118

S = 1.05

4318 reflections

172 parameters

H-atom parameters constrained

Δρmax = 0.31 e Å−3

Δρmin = −0.26 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2008 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2008 ▶); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: PLATON (Spek, 2003 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808032807/lh2707sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808032807/lh2707Isup2.hkl

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

C16H13FOS	F(000) = 568
Mr = 272.33	Dx = 1.381 Mg m−3
Monoclinic, P21/c	Melting point: 398(1) K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 29.7846 (9) Å	Cell parameters from 5213 reflections
b = 5.7070 (3) Å	θ = 4.7–32.4°
c = 7.7071 (4) Å	µ = 0.25 mm−1
β = 90.781 (3)°	T = 200 K
V = 1309.94 (10) Å3	Chunk, colourless
Z = 4	0.44 × 0.41 × 0.31 mm

Oxford Diffraction R Gemini diffractometer	4318 independent reflections
Radiation source: fine-focus sealed tube	2944 reflections with I > 2σ(I)
graphite	Rint = 0.024
Detector resolution: 10.5081 pixels mm-1	θmax = 32.5°, θmin = 4.7°
φ and ω scans	h = −44→43
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2008)	k = −8→8
Tmin = 0.945, Tmax = 1.000	l = −11→11
11708 measured reflections

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.118	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0594P)2 + 0.198P] where P = (Fo2 + 2Fc2)/3
4318 reflections	(Δ/σ)max = 0.001
172 parameters	Δρmax = 0.31 e Å−3
0 restraints	Δρmin = −0.26 e Å−3

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 > 2σ(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	0.05893 (1)	0.50390 (7)	−0.09311 (5)	0.0340 (1)
F1	0.46877 (3)	−0.30207 (18)	0.05308 (14)	0.0517 (3)
O1	0.26356 (3)	0.6477 (2)	0.26067 (15)	0.0456 (4)
C1	0.25225 (4)	0.4852 (2)	0.16574 (17)	0.0276 (3)
C2	0.28346 (4)	0.2940 (3)	0.12373 (18)	0.0301 (4)
C3	0.32640 (4)	0.3052 (3)	0.17803 (17)	0.0280 (4)
C4	0.04253 (5)	0.2032 (3)	−0.1219 (2)	0.0406 (5)
C11	0.36238 (4)	0.1383 (2)	0.14776 (16)	0.0261 (3)
C12	0.40612 (4)	0.1995 (3)	0.19971 (18)	0.0311 (4)
C13	0.44234 (4)	0.0527 (3)	0.16800 (19)	0.0348 (4)
C14	0.43389 (4)	−0.1553 (3)	0.08458 (18)	0.0340 (4)
C15	0.39128 (4)	−0.2253 (3)	0.03214 (18)	0.0320 (4)
C16	0.35546 (4)	−0.0773 (3)	0.06567 (17)	0.0284 (3)
C21	0.20523 (4)	0.4821 (2)	0.09295 (15)	0.0236 (3)
C22	0.17716 (4)	0.6710 (2)	0.12904 (17)	0.0273 (4)
C23	0.13282 (4)	0.6734 (2)	0.07161 (17)	0.0283 (4)
C24	0.11552 (4)	0.4850 (2)	−0.02440 (15)	0.0242 (3)
C25	0.14336 (4)	0.2957 (3)	−0.06185 (17)	0.0284 (4)
C26	0.18779 (4)	0.2943 (2)	−0.00286 (17)	0.0277 (3)
H2	0.27322	0.16294	0.05831	0.0361*
H3	0.33432	0.43933	0.24477	0.0336*
H4A	0.01108	0.19622	−0.16057	0.0609*
H4B	0.04601	0.11943	−0.01154	0.0609*
H4C	0.06157	0.12997	−0.20931	0.0609*
H12	0.41112	0.34423	0.25774	0.0373*
H13	0.47196	0.09498	0.20296	0.0418*
H15	0.38671	−0.37078	−0.02529	0.0384*
H16	0.32590	−0.12312	0.03247	0.0341*
H22	0.18857	0.79998	0.19391	0.0327*
H23	0.11413	0.80338	0.09752	0.0339*
H25	0.13202	0.16744	−0.12769	0.0340*
H26	0.20647	0.16408	−0.02808	0.0332*

	U11	U22	U33	U12	U13	U23
S1	0.0219 (2)	0.0389 (2)	0.0411 (2)	0.0032 (1)	−0.0038 (1)	0.0049 (2)
F1	0.0332 (4)	0.0550 (6)	0.0669 (6)	0.0198 (4)	−0.0025 (4)	−0.0060 (5)
O1	0.0307 (5)	0.0469 (7)	0.0590 (7)	0.0045 (5)	−0.0097 (5)	−0.0244 (6)
C1	0.0230 (5)	0.0306 (7)	0.0292 (6)	0.0010 (5)	0.0002 (4)	−0.0019 (6)
C2	0.0246 (6)	0.0310 (7)	0.0345 (7)	0.0028 (5)	−0.0026 (5)	−0.0051 (6)
C3	0.0265 (6)	0.0297 (7)	0.0278 (6)	0.0008 (5)	−0.0022 (5)	−0.0016 (5)
C4	0.0280 (7)	0.0479 (10)	0.0459 (8)	−0.0041 (6)	−0.0028 (6)	−0.0090 (7)
C11	0.0224 (5)	0.0306 (7)	0.0251 (6)	0.0008 (5)	−0.0025 (4)	0.0031 (5)
C12	0.0275 (6)	0.0317 (7)	0.0340 (7)	−0.0016 (5)	−0.0065 (5)	0.0002 (6)
C13	0.0235 (6)	0.0412 (9)	0.0396 (7)	0.0003 (5)	−0.0061 (5)	0.0039 (7)
C14	0.0258 (6)	0.0382 (8)	0.0378 (7)	0.0091 (5)	−0.0013 (5)	0.0040 (6)
C15	0.0306 (6)	0.0294 (7)	0.0360 (7)	0.0026 (5)	−0.0032 (5)	−0.0003 (6)
C16	0.0241 (5)	0.0302 (7)	0.0309 (6)	−0.0008 (5)	−0.0037 (5)	0.0028 (6)
C21	0.0216 (5)	0.0252 (7)	0.0239 (5)	0.0007 (5)	0.0023 (4)	0.0011 (5)
C22	0.0260 (6)	0.0239 (7)	0.0319 (6)	0.0007 (5)	0.0008 (5)	−0.0023 (5)
C23	0.0276 (6)	0.0239 (7)	0.0333 (7)	0.0062 (5)	0.0021 (5)	0.0000 (5)
C24	0.0211 (5)	0.0285 (7)	0.0230 (5)	0.0018 (5)	0.0012 (4)	0.0038 (5)
C25	0.0261 (6)	0.0286 (7)	0.0303 (6)	0.0005 (5)	−0.0016 (5)	−0.0060 (5)
C26	0.0235 (5)	0.0276 (7)	0.0319 (6)	0.0046 (5)	0.0011 (5)	−0.0045 (5)

S1—C4	1.7972 (17)	C23—C24	1.3995 (17)
S1—C24	1.7631 (12)	C24—C25	1.3945 (19)
F1—C14	1.3589 (17)	C25—C26	1.3934 (17)
O1—C1	1.2256 (17)	C2—H2	0.9500
C1—C2	1.4724 (19)	C3—H3	0.9500
C1—C21	1.5016 (17)	C4—H4A	0.9800
C2—C3	1.3418 (17)	C4—H4B	0.9800
C3—C11	1.4550 (19)	C4—H4C	0.9800
C11—C12	1.4019 (17)	C12—H12	0.9500
C11—C16	1.398 (2)	C13—H13	0.9500
C12—C13	1.390 (2)	C15—H15	0.9500
C13—C14	1.372 (2)	C16—H16	0.9500
C14—C15	1.3855 (18)	C22—H22	0.9500
C15—C16	1.388 (2)	C23—H23	0.9500
C21—C22	1.3946 (16)	C25—H25	0.9500
C21—C26	1.3976 (17)	C26—H26	0.9500
C22—C23	1.3872 (17)
S1···H4Ai	3.0100	H2···C16	2.8100
S1···H4Cii	3.0600	H2···C26	2.6900
S1···H23iii	3.1200	H2···H16	2.2700
F1···F1iv	3.0456 (14)	H2···H26	2.0900
F1···H13v	2.6300	H2···O1viii	2.9100
O1···H3	2.4200	H3···O1	2.4200
O1···H16vi	2.8900	H3···C15vi	3.0500
O1···H22	2.4400	H3···H12	2.3500
O1···H2ii	2.9100	H3···C16ii	2.6600
O1···H16ii	2.7800	H3···H16ii	2.4700
C1···C26ii	3.5900 (18)	H4A···S1x	3.0100
C3···C15vi	3.498 (2)	H4B···C25	3.1000
C3···C16ii	3.466 (2)	H4C···C25	2.8400
C12···C15vi	3.553 (2)	H4C···H25	2.1900
C15···C12vii	3.553 (2)	H4C···S1viii	3.0600
C15···C3vii	3.498 (2)	H4C···C24viii	3.0000
C16···C3viii	3.466 (2)	H12···C15vi	3.0600
C21···C26ii	3.5364 (17)	H12···H3	2.3500
C26···C21viii	3.5364 (17)	H12···C15ii	3.1000
C26···C1viii	3.5900 (18)	H13···F1xi	2.6300
C1···H26ii	2.8700	H15···C3vii	3.0300
C2···H26	2.6700	H15···C12vii	3.0500
C2···H16	2.7900	H15···C11xii	3.0300
C3···H15vi	3.0300	H15···C12xii	2.8900
C4···H25	2.6700	H15···C13xii	3.0900
C11···H15ix	3.0300	H16···O1vii	2.8900
C12···H15ix	2.8900	H16···C2	2.7900
C12···H15vi	3.0500	H16···H2	2.2700
C13···H15ix	3.0900	H16···O1viii	2.7800
C15···H12viii	3.1000	H16···H3viii	2.4700
C15···H3vii	3.0500	H22···O1	2.4400
C15···H12vii	3.0600	H23···S1xiii	3.1200
C16···H2	2.8100	H25···C4	2.6700
C16···H3viii	2.6600	H25···H4C	2.1900
C21···H26ii	3.0400	H25···C22viii	3.0200
C22···H25ii	3.0200	H25···C23viii	3.0300
C23···H25ii	3.0300	H26···C2	2.6700
C24···H4Cii	3.0000	H26···H2	2.0900
C25···H4B	3.1000	H26···C1viii	2.8700
C25···H4C	2.8400	H26···C21viii	3.0400
C26···H2	2.6900
C4—S1—C24	103.64 (6)	C1—C2—H2	120.00
O1—C1—C2	121.52 (11)	C3—C2—H2	120.00
O1—C1—C21	118.64 (11)	C2—C3—H3	116.00
C2—C1—C21	119.84 (11)	C11—C3—H3	116.00
C1—C2—C3	119.87 (14)	S1—C4—H4A	109.00
C2—C3—C11	128.30 (14)	S1—C4—H4B	109.00
C3—C11—C12	118.34 (12)	S1—C4—H4C	109.00
C3—C11—C16	122.99 (11)	H4A—C4—H4B	109.00
C12—C11—C16	118.65 (12)	H4A—C4—H4C	109.00
C11—C12—C13	121.33 (14)	H4B—C4—H4C	109.00
C12—C13—C14	117.78 (12)	C11—C12—H12	119.00
F1—C14—C13	118.77 (11)	C13—C12—H12	119.00
F1—C14—C15	118.01 (14)	C12—C13—H13	121.00
C13—C14—C15	123.21 (13)	C14—C13—H13	121.00
C14—C15—C16	118.27 (15)	C14—C15—H15	121.00
C11—C16—C15	120.74 (12)	C16—C15—H15	121.00
C1—C21—C22	118.36 (10)	C11—C16—H16	120.00
C1—C21—C26	122.99 (10)	C15—C16—H16	120.00
C22—C21—C26	118.60 (11)	C21—C22—H22	120.00
C21—C22—C23	120.98 (11)	C23—C22—H22	119.00
C22—C23—C24	120.21 (11)	C22—C23—H23	120.00
S1—C24—C23	117.09 (9)	C24—C23—H23	120.00
S1—C24—C25	123.64 (9)	C24—C25—H25	120.00
C23—C24—C25	119.27 (11)	C26—C25—H25	120.00
C24—C25—C26	120.11 (13)	C21—C26—H26	120.00
C21—C26—C25	120.83 (12)	C25—C26—H26	120.00
C4—S1—C24—C23	−155.77 (10)	C12—C13—C14—F1	−179.65 (13)
C4—S1—C24—C25	24.79 (13)	C12—C13—C14—C15	−0.4 (2)
O1—C1—C2—C3	−5.5 (2)	F1—C14—C15—C16	179.30 (13)
C21—C1—C2—C3	175.08 (12)	C13—C14—C15—C16	0.1 (2)
O1—C1—C21—C22	3.39 (18)	C14—C15—C16—C11	1.0 (2)
O1—C1—C21—C26	−173.80 (12)	C1—C21—C22—C23	−177.24 (11)
C2—C1—C21—C22	−177.22 (12)	C26—C21—C22—C23	0.08 (18)
C2—C1—C21—C26	5.60 (18)	C1—C21—C26—C25	177.44 (12)
C1—C2—C3—C11	−178.78 (13)	C22—C21—C26—C25	0.26 (19)
C2—C3—C11—C12	172.54 (15)	C21—C22—C23—C24	−0.13 (19)
C2—C3—C11—C16	−5.9 (2)	C22—C23—C24—S1	−179.63 (10)
C3—C11—C12—C13	−177.20 (13)	C22—C23—C24—C25	−0.16 (18)
C16—C11—C12—C13	1.3 (2)	S1—C24—C25—C26	179.91 (10)
C3—C11—C16—C15	176.76 (13)	C23—C24—C25—C26	0.48 (19)
C12—C11—C16—C15	−1.7 (2)	C24—C25—C26—C21	−0.5 (2)
C11—C12—C13—C14	−0.3 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O1	0.95	2.42	2.7860 (18)	102
C12—H12···Cg1ii	0.95	2.95	3.6803 (16)	134
C15—H15···Cg1xii	0.95	2.87	3.5494 (16)	129
C25—H25···Cg2viii	0.95	2.88	3.5407 (15)	127

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯O1	0.95	2.42	2.7860 (18)	102
C12—H12⋯Cg1i	0.95	2.95	3.6803 (16)	134
C15—H15⋯Cg1ii	0.95	2.87	3.5494 (16)	129
C25—H25⋯Cg2iii	0.95	2.88	3.5407 (15)	127

Symmetry codes: (i) ; (ii) ; (iii) . Cg1 and Cg2 are the centroids of the C11–C16 and C21–C26 rings.