1-{5-[2-Chloro-5-(trifluoro-meth-yl)phen-yl]thio-phen-2-yl}ethanone.

In the title molecule, C(13)H(8)ClF(3)OS, the dihedral angle between the mean planes of 2-chloro-5-(trifluoro-meth-yl)phenyl and tiophene rings is 54.37 (5)°. The acethyl group is twisted by 8.1 (2)° with respect to the thio-phene ring. The CF(3) group is disordered over two sets of sites with occupations of 0.49 (3) and 0.51 (3). The crystal packing features C-H⋯F and C-H⋯O hydrogen bonds, forming dimers which are connected into chains along the c axis by C-H⋯O hydrogen bonds and C-Cl⋯π [Cl⋯π = 3.415 (1) Å and C-Cl⋯π = 151.56 (5)°] inter-actions. The chains are further connected into layers perpendicular to the a axis by C-H⋯O inter-actions.

Related literature

For the general synthetic procedure, see: Matiychuk et al. (2010 ▶). For the biologial activity of aryl­thio­phenes, see: Reddy et al. (2005 ▶); Anderson et al. (1963 ▶); Bohlmann et al. (1984 ▶); Michaelides et al. (1997 ▶); Tanaka et al. (1998 ▶) and for their applications, see Masui et al. (2004 ▶); Roncali (1992 ▶, 1997 ▶). For methods of obtaining aryl­thio­phenes via cross-coupling reactions, see: Stanforth (1998 ▶).

Experimental

Crystal data

C13H8ClF3OS

M = 304.70

Monoclinic,

a = 15.330 (6) Å

b = 10.809 (4) Å

c = 7.676 (3) Å

β = 93.72 (3)°

V = 1269.3 (8) Å3

Z = 4

Mo Kα radiation

μ = 0.49 mm−1

T = 100 K

0.20 × 0.15 × 0.08 mm

Data collection

Kuma KM-4-CCD diffractometer

Absorption correction: analytical (CrysAlis RED; Oxford Diffraction, 2006 ▶) T min = 0.86, T max = 0.93

16021 measured reflections

4377 independent reflections

3093 reflections with I > 2σ(I)

R int = 0.034

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.097

S = 1.00

4377 reflections

201 parameters

H-atom parameters constrained

Δρmax = 0.49 e Å−3

Δρmin = −0.25 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2006 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2006 ▶); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: DIAMOND (Brandenburg, 2006) ▶; software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811003965/ds2088sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811003965/ds2088Isup2.hkl

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

C13H8ClF3OS	F(000) = 616
Mr = 304.70	Dx = 1.594 Mg m−3
Monoclinic, P21/c	Melting point: 347 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 15.330 (6) Å	Cell parameters from 11592 reflections
b = 10.809 (4) Å	θ = 2.3–33.9°
c = 7.676 (3) Å	µ = 0.49 mm−1
β = 93.72 (3)°	T = 100 K
V = 1269.3 (8) Å3	Block, colourless
Z = 4	0.20 × 0.15 × 0.08 mm

Kuma KM-4-CCD diffractometer	4377 independent reflections
Radiation source: fine-focus sealed tube	3093 reflections with I > 2σ(I)
graphite	Rint = 0.034
ω scans	θmax = 33.8°, θmin = 3.3°
Absorption correction: analytical (CrysAlis RED; Oxford Diffraction, 2006)	h = −19→23
Tmin = 0.86, Tmax = 0.93	k = −12→16
16021 measured reflections	l = −11→9

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.097	H-atom parameters constrained
S = 1.00	w = 1/[σ2(Fo2) + (0.054P)2] where P = (Fo2 + 2Fc2)/3
4377 reflections	(Δ/σ)max = 0.001
201 parameters	Δρmax = 0.49 e Å−3
0 restraints	Δρmin = −0.25 e Å−3

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	Occ. (<1)
Cl1	0.09807 (2)	0.28619 (3)	1.05277 (5)	0.02440 (10)
S1	0.37102 (2)	0.42596 (3)	1.04508 (5)	0.01971 (9)
O1	0.54239 (7)	0.39388 (9)	1.24469 (14)	0.0261 (2)
C2	0.42729 (9)	0.29067 (12)	1.08963 (19)	0.0181 (3)
C21	0.51398 (9)	0.29623 (12)	1.18365 (19)	0.0208 (3)
C22	0.56531 (10)	0.17781 (14)	1.1983 (2)	0.0276 (3)
H22A	0.5812	0.1521	1.0821	0.041*
H22B	0.5297	0.1133	1.2485	0.041*
H22C	0.6185	0.1909	1.2738	0.041*
C3	0.37969 (9)	0.18899 (12)	1.02942 (19)	0.0194 (3)
H3	0.4000	0.1062	1.0413	0.023*
C4	0.29753 (9)	0.22147 (12)	0.94833 (19)	0.0192 (3)
H4	0.2562	0.1630	0.9010	0.023*
C5	0.28396 (9)	0.34750 (11)	0.94559 (18)	0.0160 (3)
C51	0.20972 (9)	0.41760 (11)	0.86157 (18)	0.0164 (3)
C52	0.12277 (9)	0.39514 (12)	0.89694 (18)	0.0179 (3)
C53	0.05343 (9)	0.45875 (12)	0.81028 (19)	0.0192 (3)
H53	−0.0051	0.4413	0.8357	0.023*
C54	0.07070 (9)	0.54733 (12)	0.68726 (19)	0.0198 (3)
H54	0.0241	0.5907	0.6270	0.024*
C55	0.15699 (9)	0.57247 (12)	0.65236 (18)	0.0192 (3)
C1	0.17567 (10)	0.66394 (15)	0.5124 (2)	0.0289 (4)
F1	0.2540 (6)	0.7124 (13)	0.528 (2)	0.049 (3)	0.49 (3)
F2	0.1209 (7)	0.7645 (7)	0.5195 (13)	0.0485 (17)	0.49 (3)
F3	0.1634 (9)	0.6244 (10)	0.3552 (8)	0.059 (2)	0.49 (3)
F1A	0.2471 (7)	0.7292 (12)	0.549 (2)	0.052 (2)	0.51 (3)
F2A	0.1125 (5)	0.7352 (16)	0.465 (2)	0.070 (3)	0.51 (3)
F3A	0.1942 (11)	0.5975 (8)	0.3643 (11)	0.079 (2)	0.51 (3)
C56	0.22588 (9)	0.50955 (12)	0.73913 (18)	0.0189 (3)
H56	0.2843	0.5290	0.7153	0.023*

	U11	U22	U33	U12	U13	U23
Cl1	0.01931 (18)	0.02759 (17)	0.0267 (2)	−0.00030 (13)	0.00436 (14)	0.00743 (14)
S1	0.01739 (17)	0.01659 (14)	0.0246 (2)	−0.00050 (12)	−0.00288 (13)	0.00172 (13)
O1	0.0217 (5)	0.0253 (5)	0.0307 (6)	−0.0040 (4)	−0.0041 (5)	0.0034 (4)
C2	0.0151 (6)	0.0200 (6)	0.0193 (7)	0.0012 (5)	0.0017 (5)	0.0023 (5)
C21	0.0178 (7)	0.0234 (6)	0.0214 (8)	−0.0002 (5)	0.0024 (6)	0.0072 (5)
C22	0.0194 (7)	0.0266 (7)	0.0362 (10)	0.0026 (6)	−0.0034 (7)	0.0065 (6)
C3	0.0184 (7)	0.0194 (6)	0.0208 (7)	0.0027 (5)	0.0033 (6)	0.0005 (5)
C4	0.0201 (7)	0.0185 (6)	0.0189 (7)	−0.0012 (5)	0.0009 (6)	−0.0014 (5)
C5	0.0154 (6)	0.0177 (5)	0.0149 (7)	−0.0002 (5)	0.0009 (5)	−0.0005 (5)
C51	0.0164 (6)	0.0170 (5)	0.0158 (7)	0.0011 (5)	0.0002 (5)	−0.0031 (5)
C52	0.0185 (7)	0.0190 (5)	0.0163 (7)	0.0000 (5)	0.0009 (5)	−0.0009 (5)
C53	0.0138 (6)	0.0234 (6)	0.0203 (7)	0.0012 (5)	0.0007 (5)	−0.0041 (5)
C54	0.0182 (7)	0.0217 (6)	0.0190 (7)	0.0028 (5)	−0.0027 (6)	−0.0021 (5)
C55	0.0200 (7)	0.0200 (6)	0.0174 (7)	0.0005 (5)	0.0005 (5)	0.0003 (5)
C1	0.0219 (8)	0.0343 (8)	0.0300 (9)	0.0007 (6)	−0.0013 (7)	0.0102 (7)
F1	0.015 (2)	0.068 (5)	0.062 (5)	0.000 (3)	−0.003 (2)	0.043 (4)
F2	0.050 (3)	0.038 (2)	0.059 (4)	0.0255 (18)	0.020 (2)	0.0291 (19)
F3	0.115 (6)	0.043 (3)	0.0173 (15)	−0.024 (3)	−0.005 (2)	0.0037 (17)
F1A	0.053 (5)	0.049 (3)	0.053 (3)	−0.029 (3)	−0.008 (3)	0.022 (2)
F2A	0.0206 (16)	0.093 (6)	0.099 (7)	0.016 (3)	0.010 (3)	0.074 (5)
F3A	0.160 (6)	0.051 (2)	0.029 (2)	0.010 (4)	0.037 (3)	0.0148 (18)
C56	0.0169 (7)	0.0211 (6)	0.0189 (7)	−0.0004 (5)	0.0018 (5)	−0.0017 (5)

Cl1—C52	1.738 (2)	C51—C56	1.401 (2)
S1—C5	1.718 (2)	C52—C53	1.398 (2)
S1—C2	1.721 (2)	C53—C54	1.382 (2)
O1—C21	1.224 (2)	C53—H53	0.9500
C2—C3	1.382 (2)	C54—C55	1.393 (2)
C2—C21	1.472 (2)	C54—H54	0.9500
C21—C22	1.503 (2)	C55—C56	1.389 (2)
C22—H22A	0.9800	C55—C1	1.501 (2)
C22—H22B	0.9800	C1—F2A	1.272 (8)
C22—H22C	0.9800	C1—F3	1.282 (8)
C3—C4	1.413 (2)	C1—F1	1.309 (10)
C3—H3	0.9500	C1—F1A	1.317 (11)
C4—C5	1.378 (2)	C1—F2	1.377 (7)
C4—H4	0.9500	C1—F3A	1.389 (8)
C5—C51	1.480 (2)	C56—H56	0.9500
C51—C52	1.399 (2)
C5—S1—C2	91.94 (7)	C53—C52—Cl1	117.91 (11)
C3—C2—C21	129.54 (12)	C51—C52—Cl1	120.28 (11)
C3—C2—S1	111.25 (11)	C54—C53—C52	119.50 (13)
C21—C2—S1	119.20 (10)	C54—C53—H53	120.3
O1—C21—C2	120.70 (13)	C52—C53—H53	120.3
O1—C21—C22	122.31 (14)	C53—C54—C55	119.52 (13)
C2—C21—C22	116.98 (12)	C53—C54—H54	120.2
C21—C22—H22A	109.5	C55—C54—H54	120.2
C21—C22—H22B	109.5	C56—C55—C54	120.92 (13)
H22A—C22—H22B	109.5	C56—C55—C1	119.42 (13)
C21—C22—H22C	109.5	C54—C55—C1	119.58 (13)
H22A—C22—H22C	109.5	F3—C1—F1	107.4 (8)
H22B—C22—H22C	109.5	F2A—C1—F1A	110.1 (7)
C2—C3—C4	112.70 (12)	F3—C1—F2	104.4 (6)
C2—C3—H3	123.7	F1—C1—F2	103.8 (7)
C4—C3—H3	123.7	F2A—C1—F3A	105.6 (6)
C5—C4—C3	112.45 (12)	F1A—C1—F3A	103.8 (8)
C5—C4—H4	123.8	F2A—C1—C55	115.3 (4)
C3—C4—H4	123.8	F3—C1—C55	115.5 (4)
C4—C5—C51	128.60 (12)	F1—C1—C55	114.4 (6)
C4—C5—S1	111.66 (10)	F1A—C1—C55	113.4 (6)
C51—C5—S1	119.62 (10)	F2—C1—C55	110.3 (4)
C52—C51—C56	117.75 (12)	F3A—C1—C55	107.7 (4)
C52—C51—C5	122.83 (12)	C55—C56—C51	120.46 (13)
C56—C51—C5	119.41 (12)	C55—C56—H56	119.8
C53—C52—C51	121.81 (13)	C51—C56—H56	119.8

D—H···A	D—H	H···A	D···A	D—H···A
C22—H22C···F1Ai	0.98	2.55	3.520 (13)	168
C22—H22B···O1ii	0.98	2.62	3.526 (2)	154
C22—H22A···O1iii	0.98	2.67	3.562 (3)	152
C56—H56···O1i	0.95	2.78	3.697 (2)	162

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C22—H22C⋯F1Ai	0.98	2.55	3.520 (13)	168
C22—H22B⋯O1ii	0.98	2.62	3.526 (2)	154
C22—H22A⋯O1iii	0.98	2.67	3.562 (3)	152
C56—H56⋯O1i	0.95	2.78	3.697 (2)	162

Symmetry codes: (i) ; (ii) ; (iii) .