Methyl 2-[4-(tri-fluoro-meth-yl)phenyl-sulfan-yl]benzoate.

In the title compound, C15H13F3O2S, the dihedral angle between the benzene rings is 79.5 (1)°. The ester group is twisted by 7.6 (1)° from the mean plane of the adjacent benzene ring. Disorder was modeled over two sites for one F atom of the tri-fluoro-methyl group with an occupancy ratio of 0.54 (6):0.46 (6). In the crystal, mol-ecules are linked via weak C-H⋯O hydrogen bonds, forming two-dimensional networks lying parallel to (101). The networks are linked via C-H⋯π inter-actions, leading to the formation of a three-dimensional supra-molecular structure.

Related literature

For general background and pharmacological properties of the neuroleptic agent flupentixol [systematic name: (EZ)-2-[4-[3-[2-(tri­fluoro­meth­yl)thioxanthen-9-yl­idene]prop­yl]pip­era­zin-1-yl]ethanol] and related compounds, see: Ovhed (1976 ▶); Robertson & Trimble (1981 ▶); Valle-Jones & Swarbrick (1981 ▶); Young et al. (1976 ▶). For related structures, see: Post et al. (1975a ▶,b ▶); Siddegowda et al. (2011a ▶,b ▶). For standard bond lengths, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C15H11F3O2S

M = 312.30

Monoclinic,

a = 11.0675 (5) Å

b = 8.0429 (3) Å

c = 15.6614 (7) Å

β = 96.654 (5)°

V = 1384.70 (11) Å3

Z = 4

Cu Kα radiation

μ = 2.44 mm−1

T = 173 K

0.28 × 0.22 × 0.12 mm

Data collection

Agilent Gemini EOS diffractometer

Absorption correction: multi-scan (CrysAlis PRO and CrysAlis RED; Agilent, 2012 ▶) T min = 0.715, T max = 1.000

8110 measured reflections

2705 independent reflections

2224 reflections with I > 2σ(I)

R int = 0.039

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.123

S = 1.03

2705 reflections

201 parameters

H-atom parameters constrained

Δρmax = 0.36 e Å−3

Δρmin = −0.27 e Å−3

Data collection: CrysAlis PRO (Agilent, 2012 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis RED (Agilent, 2012 ▶); 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/S1600536813028146/su2658sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813028146/su2658Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813028146/su2658Isup3.cml

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

C15H11F3O2S	F(000) = 640
Mr = 312.30	Dx = 1.498 Mg m−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.54184 Å
a = 11.0675 (5) Å	Cell parameters from 2806 reflections
b = 8.0429 (3) Å	θ = 4.0–72.2°
c = 15.6614 (7) Å	µ = 2.44 mm−1
β = 96.654 (5)°	T = 173 K
V = 1384.70 (11) Å3	Block, colourless
Z = 4	0.28 × 0.22 × 0.12 mm

Agilent Gemini EOS diffractometer	2705 independent reflections
Radiation source: Enhance (Cu) X-ray Source	2224 reflections with I > 2σ(I)
Detector resolution: 16.0416 pixels mm-1	Rint = 0.039
ω scans	θmax = 72.4°, θmin = 4.0°
Absorption correction: multi-scan (CrysAlis PRO and CrysAlis RED; Agilent, 2012)	h = −13→10
Tmin = 0.715, Tmax = 1.000	k = −9→7
8110 measured reflections	l = −18→19

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.043	H-atom parameters constrained
wR(F2) = 0.123	w = 1/[σ2(Fo2) + (0.0689P)2 + 0.2842P] where P = (Fo2 + 2Fc2)/3
S = 1.03	(Δ/σ)max < 0.001
2705 reflections	Δρmax = 0.36 e Å−3
201 parameters	Δρmin = −0.27 e Å−3
0 restraints

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	0.74068 (5)	0.20434 (6)	0.53524 (4)	0.03547 (18)
F1	1.15258 (18)	0.4950 (3)	0.29524 (12)	0.0867 (7)
F2	1.02027 (17)	0.4280 (3)	0.19408 (10)	0.0764 (6)
F3	1.1534 (11)	0.257 (2)	0.2621 (9)	0.078 (3)	0.54 (6)
F3A	1.121 (4)	0.234 (3)	0.240 (3)	0.127 (7)	0.46 (6)
O1	0.50339 (13)	−0.10252 (18)	0.67852 (9)	0.0370 (4)
O2	0.61424 (16)	0.1251 (2)	0.66627 (11)	0.0504 (5)
C1	0.58173 (17)	−0.0107 (3)	0.64017 (13)	0.0289 (4)
C2	0.62526 (16)	−0.0927 (2)	0.56503 (12)	0.0268 (4)
C3	0.59456 (18)	−0.2586 (3)	0.54673 (13)	0.0314 (4)
H3	0.5458	−0.3151	0.5816	0.038*
C4	0.63512 (19)	−0.3401 (3)	0.47797 (14)	0.0354 (5)
H4	0.6149	−0.4509	0.4670	0.042*
C5	0.70653 (19)	−0.2546 (3)	0.42526 (13)	0.0343 (5)
H5	0.7332	−0.3082	0.3783	0.041*
C6	0.73828 (18)	−0.0906 (3)	0.44206 (13)	0.0313 (4)
H6	0.7866	−0.0355	0.4063	0.038*
C7	0.69912 (16)	−0.0063 (2)	0.51164 (13)	0.0271 (4)
C8	0.83570 (18)	0.2519 (2)	0.45386 (13)	0.0310 (4)
C9	0.78756 (19)	0.2956 (3)	0.37134 (15)	0.0352 (5)
H9	0.7037	0.2965	0.3566	0.042*
C10	0.8636 (2)	0.3378 (3)	0.31074 (14)	0.0368 (5)
H10	0.8312	0.3660	0.2552	0.044*
C11	0.98830 (19)	0.3377 (3)	0.33316 (14)	0.0345 (5)
C12	1.0368 (2)	0.2971 (3)	0.41589 (15)	0.0435 (6)
H12	1.1205	0.2989	0.4310	0.052*
C13	0.9604 (2)	0.2538 (3)	0.47609 (15)	0.0419 (5)
H13	0.9929	0.2258	0.5317	0.050*
C14	1.0745 (2)	0.3760 (3)	0.26912 (17)	0.0493 (6)
C15	0.4586 (2)	−0.0262 (3)	0.75237 (14)	0.0406 (5)
H15A	0.4236	0.0801	0.7363	0.061*
H15B	0.5247	−0.0117	0.7972	0.061*
H15C	0.3979	−0.0964	0.7727	0.061*

	U11	U22	U33	U12	U13	U23
S1	0.0389 (3)	0.0280 (3)	0.0428 (3)	−0.0061 (2)	0.0183 (2)	−0.0040 (2)
F1	0.0817 (12)	0.1103 (16)	0.0725 (12)	−0.0512 (12)	0.0279 (10)	0.0079 (11)
F2	0.0827 (12)	0.1077 (16)	0.0416 (9)	−0.0139 (11)	0.0196 (8)	0.0172 (9)
F3	0.078 (6)	0.083 (8)	0.083 (5)	0.030 (4)	0.054 (5)	0.025 (4)
F3A	0.196 (15)	0.049 (4)	0.166 (15)	0.017 (9)	0.151 (12)	0.011 (8)
O1	0.0469 (9)	0.0324 (8)	0.0350 (8)	−0.0067 (6)	0.0189 (7)	−0.0022 (6)
O2	0.0583 (10)	0.0422 (9)	0.0564 (11)	−0.0182 (8)	0.0304 (8)	−0.0184 (8)
C1	0.0261 (9)	0.0314 (10)	0.0295 (10)	−0.0011 (8)	0.0042 (7)	0.0000 (8)
C2	0.0229 (9)	0.0297 (10)	0.0277 (9)	−0.0004 (7)	0.0020 (7)	0.0010 (7)
C3	0.0304 (10)	0.0308 (10)	0.0335 (10)	−0.0052 (8)	0.0061 (8)	0.0007 (8)
C4	0.0392 (11)	0.0281 (10)	0.0391 (12)	−0.0053 (9)	0.0057 (9)	−0.0051 (8)
C5	0.0378 (11)	0.0345 (11)	0.0316 (10)	0.0019 (9)	0.0082 (9)	−0.0058 (8)
C6	0.0310 (10)	0.0327 (11)	0.0317 (10)	0.0014 (8)	0.0099 (8)	0.0034 (8)
C7	0.0249 (9)	0.0246 (9)	0.0320 (10)	0.0007 (7)	0.0036 (7)	0.0013 (7)
C8	0.0329 (10)	0.0251 (9)	0.0368 (11)	−0.0028 (8)	0.0117 (8)	0.0011 (8)
C9	0.0293 (10)	0.0331 (11)	0.0429 (12)	0.0018 (8)	0.0027 (9)	0.0012 (9)
C10	0.0433 (12)	0.0341 (11)	0.0325 (11)	0.0014 (9)	0.0031 (9)	0.0049 (9)
C11	0.0394 (11)	0.0300 (11)	0.0353 (11)	−0.0036 (9)	0.0098 (9)	0.0018 (8)
C12	0.0289 (11)	0.0611 (16)	0.0407 (13)	−0.0067 (10)	0.0046 (9)	0.0080 (11)
C13	0.0361 (12)	0.0558 (14)	0.0337 (11)	−0.0031 (10)	0.0039 (9)	0.0097 (10)
C14	0.0543 (15)	0.0508 (15)	0.0458 (14)	−0.0043 (12)	0.0186 (11)	0.0103 (11)
C15	0.0508 (13)	0.0427 (13)	0.0315 (11)	−0.0040 (10)	0.0179 (9)	−0.0010 (9)

S1—C7	1.783 (2)	C5—C6	1.382 (3)
S1—C8	1.785 (2)	C6—H6	0.9300
F1—C14	1.322 (3)	C6—C7	1.394 (3)
F2—C14	1.324 (3)	C8—C9	1.385 (3)
F3—C14	1.311 (13)	C8—C13	1.384 (3)
F3A—C14	1.354 (19)	C9—H9	0.9300
O1—C1	1.334 (2)	C9—C10	1.382 (3)
O1—C15	1.446 (2)	C10—H10	0.9300
O2—C1	1.206 (3)	C10—C11	1.384 (3)
C1—C2	1.478 (3)	C11—C12	1.383 (3)
C2—C3	1.398 (3)	C11—C14	1.494 (3)
C2—C7	1.417 (3)	C12—H12	0.9300
C3—H3	0.9300	C12—C13	1.382 (3)
C3—C4	1.380 (3)	C13—H13	0.9300
C4—H4	0.9300	C15—H15A	0.9600
C4—C5	1.389 (3)	C15—H15B	0.9600
C5—H5	0.9300	C15—H15C	0.9600
C7—S1—C8	102.41 (9)	C10—C9—H9	119.9
C1—O1—C15	115.20 (17)	C9—C10—H10	120.2
O1—C1—C2	113.60 (17)	C9—C10—C11	119.6 (2)
O2—C1—O1	122.19 (19)	C11—C10—H10	120.2
O2—C1—C2	124.20 (18)	C10—C11—C14	121.7 (2)
C3—C2—C1	119.69 (18)	C12—C11—C10	120.3 (2)
C3—C2—C7	119.33 (18)	C12—C11—C14	118.0 (2)
C7—C2—C1	120.97 (18)	C11—C12—H12	120.1
C2—C3—H3	119.3	C13—C12—C11	119.8 (2)
C4—C3—C2	121.35 (19)	C13—C12—H12	120.1
C4—C3—H3	119.3	C8—C13—H13	119.9
C3—C4—H4	120.4	C12—C13—C8	120.1 (2)
C3—C4—C5	119.17 (19)	C12—C13—H13	119.9
C5—C4—H4	120.4	F1—C14—F2	105.0 (2)
C4—C5—H5	119.7	F1—C14—F3A	117 (2)
C6—C5—C4	120.58 (19)	F1—C14—C11	112.7 (2)
C6—C5—H5	119.7	F2—C14—F3A	97 (2)
C5—C6—H6	119.4	F2—C14—C11	113.7 (2)
C5—C6—C7	121.16 (19)	F3—C14—F1	98.0 (8)
C7—C6—H6	119.4	F3—C14—F2	113.3 (7)
C2—C7—S1	119.74 (15)	F3—C14—C11	112.8 (7)
C6—C7—S1	121.86 (15)	F3A—C14—C11	110.7 (8)
C6—C7—C2	118.40 (18)	O1—C15—H15A	109.5
C9—C8—S1	121.72 (16)	O1—C15—H15B	109.5
C13—C8—S1	118.39 (16)	O1—C15—H15C	109.5
C13—C8—C9	119.78 (19)	H15A—C15—H15B	109.5
C8—C9—H9	119.9	H15A—C15—H15C	109.5
C10—C9—C8	120.3 (2)	H15B—C15—H15C	109.5
S1—C8—C9—C10	177.55 (16)	C8—S1—C7—C6	−1.42 (18)
S1—C8—C13—C12	−177.2 (2)	C8—C9—C10—C11	−0.6 (3)
O1—C1—C2—C3	−7.3 (3)	C9—C8—C13—C12	−0.8 (4)
O1—C1—C2—C7	173.53 (17)	C9—C10—C11—C12	−0.5 (3)
O2—C1—C2—C3	171.6 (2)	C9—C10—C11—C14	177.6 (2)
O2—C1—C2—C7	−7.6 (3)	C10—C11—C12—C13	1.0 (4)
C1—C2—C3—C4	−178.95 (19)	C10—C11—C14—F1	127.0 (3)
C1—C2—C7—S1	0.1 (2)	C10—C11—C14—F2	7.6 (4)
C1—C2—C7—C6	179.48 (17)	C10—C11—C14—F3	−123.1 (8)
C2—C3—C4—C5	−0.9 (3)	C10—C11—C14—F3A	−100 (2)
C3—C2—C7—S1	−179.11 (15)	C11—C12—C13—C8	−0.4 (4)
C3—C2—C7—C6	0.3 (3)	C12—C11—C14—F1	−54.9 (3)
C3—C4—C5—C6	1.0 (3)	C12—C11—C14—F2	−174.2 (2)
C4—C5—C6—C7	−0.4 (3)	C12—C11—C14—F3	55.0 (9)
C5—C6—C7—S1	179.17 (16)	C12—C11—C14—F3A	78 (2)
C5—C6—C7—C2	−0.2 (3)	C13—C8—C9—C10	1.3 (3)
C7—S1—C8—C9	81.16 (19)	C14—C11—C12—C13	−177.2 (2)
C7—S1—C8—C13	−102.49 (19)	C15—O1—C1—O2	1.2 (3)
C7—C2—C3—C4	0.3 (3)	C15—O1—C1—C2	−179.96 (17)
C8—S1—C7—C2	177.93 (15)

D—H···A	D—H	H···A	D···A	D—H···A
C15—H15C···O2i	0.96	2.45	3.221 (3)	138
C12—H12···Cgii	0.93	2.70	3.558 (2)	154

Table 1

Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C2–C7 benzene ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C15—H15C⋯O2i	0.96	2.45	3.221 (3)	138
C12—H12⋯Cg ii	0.93	2.70	3.558 (2)	154

Symmetry codes: (i) ; (ii) .