2-[4-(Tri-fluoro-meth-yl)phenyl-sulfan-yl]benzoic acid.

In the title compound, C14H9F3O2S, the dihedral angle between the mean planes of the benzene rings is 88.7 (2)°. The carb-oxy-lic acid group is twisted by 13.6 (7)° from the mean plane of its attached aromatic ring. One of the F atoms of the tri-fluoro-methyl group is disordered over two sites in a 0.61 (7):0.39 (7) ratio. In the crystal, inversion dimers linked by pairs of O-H⋯O hydrogen bonds generate R 2 (2)(8) loops. Weak C-H⋯F inter-actions are also observed.

Related literature

For background to the neuroleptic agent flupentixol (systematic name: (EZ)-2-[4-[3-[2-(tri­fluoro­meth­yl)thio­xan­then-9-yl­idene]prop­yl]piperazin-1-yl]ethanol), see: Young et al. (1976 ▶). For related structures, see: Post et al. (1975a ▶,b ▶); Siddegowda et al. (2011a ▶,b ▶).

Experimental

Crystal data

C14H9F3O2S

M = 298.28

Triclinic,

a = 7.3071 (5) Å

b = 8.0790 (7) Å

c = 11.3878 (11) Å

α = 82.678 (8)°

β = 83.642 (7)°

γ = 72.309 (7)°

V = 633.41 (10) Å3

Z = 2

Cu Kα radiation

μ = 2.63 mm−1

T = 173 K

0.24 × 0.22 × 0.12 mm

Data collection

Agilent Gemini EOS diffractometer

Absorption correction: multi-scan (CrysAlis PRO and CrysAlis RED; Agilent, 2012 ▶) T min = 0.848, T max = 1.000

3701 measured reflections

2419 independent reflections

2049 reflections with I > 2σ(I)

R int = 0.038

Refinement

R[F 2 > 2σ(F 2)] = 0.054

wR(F 2) = 0.155

S = 1.04

2419 reflections

193 parameters

H-atom parameters constrained

Δρmax = 0.71 e Å−3

Δρmin = −0.38 e Å−3

Data collection: CrysAlis PRO (Agilent, 2012 ▶); cell refinement: CrysAlis PRO (Agilent, 2012 ▶); data reduction: CrysAlis RED; program(s) used to solve structure: SUPERFLIP (Palatinus & Chapuis, 2007 ▶); program(s) used to refine structure: SHELXL2012 (Sheldrick, 2008 ▶); molecular graphics: OLEX2 (Dolomanov et al., 2009 ▶); software used to prepare material for publication: OLEX2.

Crystal structure: contains datablock(s) I. DOI: 10.1107/S1600536813028778/hb7150sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813028778/hb7150Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813028778/hb7150Isup3.cml

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

C14H9F3O2S	Z = 2
Mr = 298.28	F(000) = 304
Triclinic, P1	Dx = 1.564 Mg m−3
a = 7.3071 (5) Å	Cu Kα radiation, λ = 1.54184 Å
b = 8.0790 (7) Å	Cell parameters from 1645 reflections
c = 11.3878 (11) Å	θ = 5.8–72.1°
α = 82.678 (8)°	µ = 2.63 mm−1
β = 83.642 (7)°	T = 173 K
γ = 72.309 (7)°	Irregular, colourless
V = 633.41 (10) Å3	0.24 × 0.22 × 0.12 mm

Agilent Gemini EOS diffractometer	2419 independent reflections
Radiation source: Enhance (Cu) X-ray Source	2049 reflections with I > 2σ(I)
Detector resolution: 16.0416 pixels mm-1	Rint = 0.038
ω scans	θmax = 72.2°, θmin = 5.8°
Absorption correction: multi-scan (CrysAlis PRO and CrysAlis RED; Agilent, 2012)	h = −8→6
Tmin = 0.848, Tmax = 1.000	k = −9→6
3701 measured reflections	l = −13→14

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.054	w = 1/[σ2(Fo2) + (0.0889P)2 + 0.2312P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.155	(Δ/σ)max < 0.001
S = 1.04	Δρmax = 0.71 e Å−3
2419 reflections	Δρmin = −0.38 e Å−3
193 parameters	Extinction correction: SHELXL2012 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
0 restraints	Extinction coefficient: 0.0044 (14)
Primary atom site location: structure-invariant direct methods

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

	x	y	z	Uiso*/Ueq	Occ. (<1)
S1	0.51402 (10)	0.35821 (8)	0.70404 (6)	0.0398 (3)
F1	1.2832 (3)	0.1041 (3)	1.0280 (2)	0.0764 (7)
F2	1.0648 (3)	0.1392 (4)	1.16595 (19)	0.0849 (8)
F3	1.1664 (14)	0.3549 (10)	1.0613 (12)	0.054 (2)	0.61 (7)
F3A	1.094 (10)	0.3613 (16)	1.106 (6)	0.100 (14)	0.39 (7)
O1	0.2047 (3)	0.4458 (2)	0.56512 (17)	0.0405 (5)
O2	−0.0035 (3)	0.7122 (2)	0.54064 (19)	0.0427 (5)
H2	−0.0646	0.6592	0.5121	0.064*
C1	0.1620 (4)	0.6021 (3)	0.5733 (2)	0.0332 (5)
C2	0.2907 (4)	0.6861 (3)	0.6177 (2)	0.0316 (5)
C3	0.2487 (4)	0.8678 (3)	0.5973 (2)	0.0376 (6)
H3	0.1387	0.9315	0.5595	0.045*
C4	0.3668 (4)	0.9550 (3)	0.6319 (2)	0.0396 (6)
H4	0.3375	1.0757	0.6172	0.048*
C5	0.5291 (4)	0.8595 (4)	0.6888 (2)	0.0400 (6)
H5	0.6098	0.9166	0.7125	0.048*
C6	0.5730 (4)	0.6794 (3)	0.7109 (2)	0.0362 (6)
H6	0.6825	0.6174	0.7497	0.043*
C7	0.4555 (3)	0.5897 (3)	0.6759 (2)	0.0303 (5)
C8	0.6908 (4)	0.3131 (3)	0.8091 (2)	0.0328 (5)
C9	0.6355 (4)	0.3133 (3)	0.9291 (2)	0.0378 (6)
H9	0.5055	0.3396	0.9548	0.045*
C10	0.7722 (4)	0.2748 (4)	1.0114 (2)	0.0405 (6)
H10	0.7343	0.2740	1.0921	0.049*
C11	0.9646 (4)	0.2375 (3)	0.9731 (2)	0.0335 (6)
C12	1.0216 (4)	0.2340 (4)	0.8540 (3)	0.0447 (7)
H12	1.1518	0.2070	0.8288	0.054*
C13	0.8857 (4)	0.2704 (4)	0.7719 (3)	0.0461 (7)
H13	0.9246	0.2663	0.6915	0.055*
C14	1.1122 (4)	0.2104 (4)	1.0605 (3)	0.0450 (7)

	U11	U22	U33	U12	U13	U23
S1	0.0441 (4)	0.0305 (4)	0.0495 (4)	−0.0120 (3)	−0.0242 (3)	−0.0013 (3)
F1	0.0508 (12)	0.0796 (15)	0.0942 (17)	0.0002 (10)	−0.0385 (11)	−0.0105 (12)
F2	0.0770 (15)	0.134 (2)	0.0508 (12)	−0.0459 (15)	−0.0335 (10)	0.0265 (12)
F3	0.057 (5)	0.0356 (19)	0.078 (4)	−0.0181 (19)	−0.034 (4)	−0.002 (2)
F3A	0.15 (3)	0.034 (3)	0.14 (2)	−0.024 (7)	−0.11 (2)	−0.002 (6)
O1	0.0417 (10)	0.0349 (10)	0.0504 (11)	−0.0126 (8)	−0.0228 (8)	−0.0039 (8)
O2	0.0356 (10)	0.0404 (10)	0.0559 (12)	−0.0100 (8)	−0.0219 (8)	−0.0055 (9)
C1	0.0336 (13)	0.0385 (14)	0.0295 (12)	−0.0123 (10)	−0.0104 (10)	0.0000 (10)
C2	0.0343 (13)	0.0335 (12)	0.0293 (12)	−0.0112 (10)	−0.0075 (9)	−0.0039 (9)
C3	0.0381 (13)	0.0339 (13)	0.0410 (14)	−0.0075 (11)	−0.0138 (11)	−0.0026 (10)
C4	0.0456 (15)	0.0300 (13)	0.0460 (15)	−0.0124 (11)	−0.0143 (12)	−0.0016 (11)
C5	0.0415 (15)	0.0410 (15)	0.0452 (15)	−0.0190 (12)	−0.0141 (12)	−0.0055 (11)
C6	0.0331 (13)	0.0373 (14)	0.0412 (14)	−0.0117 (11)	−0.0143 (11)	−0.0019 (11)
C7	0.0308 (12)	0.0316 (12)	0.0302 (12)	−0.0101 (10)	−0.0078 (9)	−0.0023 (9)
C8	0.0339 (12)	0.0267 (12)	0.0393 (13)	−0.0082 (9)	−0.0143 (10)	−0.0009 (10)
C9	0.0317 (13)	0.0391 (14)	0.0441 (15)	−0.0103 (11)	−0.0066 (11)	−0.0067 (11)
C10	0.0466 (15)	0.0464 (16)	0.0333 (13)	−0.0192 (12)	−0.0066 (11)	−0.0041 (11)
C11	0.0387 (13)	0.0219 (11)	0.0424 (14)	−0.0100 (9)	−0.0145 (11)	−0.0005 (9)
C12	0.0320 (13)	0.0542 (17)	0.0466 (16)	−0.0077 (12)	−0.0078 (11)	−0.0086 (13)
C13	0.0395 (15)	0.0595 (18)	0.0365 (14)	−0.0091 (13)	−0.0037 (11)	−0.0071 (13)
C14	0.0550 (18)	0.0317 (13)	0.0538 (17)	−0.0154 (12)	−0.0258 (14)	0.0006 (12)

S1—C7	1.782 (2)	C5—H5	0.9300
S1—C8	1.783 (2)	C5—C6	1.387 (4)
F1—C14	1.328 (4)	C6—H6	0.9300
F2—C14	1.322 (4)	C6—C7	1.396 (3)
F3—C14	1.343 (8)	C8—C9	1.381 (4)
F3A—C14	1.35 (2)	C8—C13	1.390 (4)
O1—C1	1.218 (3)	C9—H9	0.9300
O2—H2	0.8200	C9—C10	1.384 (4)
O2—C1	1.324 (3)	C10—H10	0.9300
C1—C2	1.477 (3)	C10—C11	1.378 (4)
C2—C3	1.400 (4)	C11—C12	1.375 (4)
C2—C7	1.404 (3)	C11—C14	1.496 (4)
C3—H3	0.9300	C12—H12	0.9300
C3—C4	1.383 (4)	C12—C13	1.380 (4)
C4—H4	0.9300	C13—H13	0.9300
C4—C5	1.381 (4)
C7—S1—C8	101.59 (11)	C13—C8—S1	120.6 (2)
C1—O2—H2	109.5	C8—C9—H9	119.7
O1—C1—O2	122.6 (2)	C8—C9—C10	120.5 (2)
O1—C1—C2	123.3 (2)	C10—C9—H9	119.7
O2—C1—C2	114.1 (2)	C9—C10—H10	120.2
C3—C2—C1	118.3 (2)	C11—C10—C9	119.7 (2)
C3—C2—C7	119.4 (2)	C11—C10—H10	120.2
C7—C2—C1	122.3 (2)	C10—C11—C14	120.1 (2)
C2—C3—H3	119.2	C12—C11—C10	120.3 (2)
C4—C3—C2	121.6 (2)	C12—C11—C14	119.5 (3)
C4—C3—H3	119.2	C11—C12—H12	120.0
C3—C4—H4	120.6	C11—C12—C13	120.0 (3)
C5—C4—C3	118.8 (2)	C13—C12—H12	120.0
C5—C4—H4	120.6	C8—C13—H13	119.9
C4—C5—H5	119.7	C12—C13—C8	120.2 (3)
C4—C5—C6	120.7 (2)	C12—C13—H13	119.9
C6—C5—H5	119.7	F1—C14—F3	97.8 (5)
C5—C6—H6	119.5	F1—C14—F3A	122 (3)
C5—C6—C7	121.1 (2)	F1—C14—C11	113.7 (2)
C7—C6—H6	119.5	F2—C14—F1	104.4 (2)
C2—C7—S1	120.83 (18)	F2—C14—F3	115.3 (6)
C6—C7—S1	120.71 (19)	F2—C14—F3A	91 (3)
C6—C7—C2	118.5 (2)	F2—C14—C11	113.2 (2)
C9—C8—S1	120.1 (2)	F3—C14—C11	111.3 (4)
C9—C8—C13	119.2 (2)	F3A—C14—C11	110.3 (8)
S1—C8—C9—C10	178.6 (2)	C8—S1—C7—C2	−165.8 (2)
S1—C8—C13—C12	−179.4 (2)	C8—S1—C7—C6	14.5 (2)
O1—C1—C2—C3	165.0 (3)	C8—C9—C10—C11	0.6 (4)
O1—C1—C2—C7	−13.0 (4)	C9—C8—C13—C12	−2.0 (4)
O2—C1—C2—C3	−13.7 (3)	C9—C10—C11—C12	−1.7 (4)
O2—C1—C2—C7	168.3 (2)	C9—C10—C11—C14	174.9 (2)
C1—C2—C3—C4	−177.4 (2)	C10—C11—C12—C13	1.0 (4)
C1—C2—C7—S1	−2.1 (3)	C10—C11—C14—F1	151.3 (3)
C1—C2—C7—C6	177.6 (2)	C10—C11—C14—F2	32.4 (4)
C2—C3—C4—C5	−0.5 (4)	C10—C11—C14—F3	−99.4 (7)
C3—C2—C7—S1	179.85 (19)	C10—C11—C14—F3A	−68 (4)
C3—C2—C7—C6	−0.4 (4)	C11—C12—C13—C8	0.9 (5)
C3—C4—C5—C6	0.0 (4)	C12—C11—C14—F1	−32.1 (4)
C4—C5—C6—C7	0.3 (4)	C12—C11—C14—F2	−151.0 (3)
C5—C6—C7—S1	179.6 (2)	C12—C11—C14—F3	77.2 (7)
C5—C6—C7—C2	−0.1 (4)	C12—C11—C14—F3A	109 (4)
C7—S1—C8—C9	89.1 (2)	C13—C8—C9—C10	1.2 (4)
C7—S1—C8—C13	−93.5 (2)	C14—C11—C12—C13	−175.6 (3)
C7—C2—C3—C4	0.7 (4)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O1i	0.82	1.86	2.677 (3)	175
C6—H6···F3ii	0.93	2.59	3.319 (10)	136
C6—H6···F3Aii	0.93	2.50	3.294 (16)	144

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯O1i	0.82	1.86	2.677 (3)	175
C6—H6⋯F3ii	0.93	2.59	3.319 (10)	136
C6—H6⋯F3A ii	0.93	2.50	3.294 (16)	144

Symmetry codes: (i) ; (ii) .