2,2,2-Trifluoro-ethyl 4-methyl-benzene-sulfonate.

In the crystal structure of the title compound, C(9)H(9)F(3)O(3)S, inter-molecular C-H⋯O hydrogen bonds link the mol-ecules along the c-axis direction. Also present are slipped π-π stacking inter-actions between phenyl-ene rings, with perpendicular inter-planar distances of 3.55 (2) Å and centroid-centroid distances of 3.851 (2) Å.

Related literature

The title compound is a reactive electrophile and a useful inter­mediate in organic synthesis. For general background and the synthesis, see: Gøgsig et al. (2008 ▶). For a similar structure, see: Asano et al. (2009 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C9H9F3O3S

M = 254.22

Monoclinic,

a = 8.3760 (17) Å

b = 11.827 (2) Å

c = 11.145 (2) Å

β = 94.54 (3)°

V = 1100.6 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.33 mm−1

T = 293 K

0.30 × 0.10 × 0.10 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

Absorption correction: ψ scan (North et al., 1968 ▶) T min = 0.909, T max = 0.968

2149 measured reflections

2005 independent reflections

1355 reflections with I > 2σ(I)

R int = 0.012

3 standard reflections every 200 reflections intensity decay: 1%

Refinement

R[F 2 > 2σ(F 2)] = 0.057

wR(F 2) = 0.172

S = 1.00

2005 reflections

146 parameters

H-atom parameters constrained

Δρmax = 0.21 e Å−3

Δρmin = −0.29 e Å−3

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1989 ▶); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810038894/zl2306sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810038894/zl2306Isup2.hkl

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

C9H9F3O3S	F(000) = 520
Mr = 254.22	Dx = 1.534 Mg m−3
Monoclinic, P21/c	Melting point: 312 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 8.3760 (17) Å	Cell parameters from 25 reflections
b = 11.827 (2) Å	θ = 9–13°
c = 11.145 (2) Å	µ = 0.33 mm−1
β = 94.54 (3)°	T = 293 K
V = 1100.6 (4) Å3	Needle, colourless
Z = 4	0.30 × 0.10 × 0.10 mm

Enraf–Nonius CAD-4 diffractometer	1355 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.012
graphite	θmax = 25.3°, θmin = 2.4°
ω/2θ scans	h = 0→10
Absorption correction: ψ scan (North et al., 1968)	k = 0→14
Tmin = 0.909, Tmax = 0.968	l = −13→13
2149 measured reflections	3 standard reflections every 200 reflections
2005 independent reflections	intensity decay: 1%

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)] = 0.057	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.172	H-atom parameters constrained
S = 1.00	w = 1/[σ2(Fo2) + (0.1P)2 + 0.350P] where P = (Fo2 + 2Fc2)/3
2005 reflections	(Δ/σ)max < 0.001
146 parameters	Δρmax = 0.21 e Å−3
0 restraints	Δρmin = −0.29 e Å−3

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.

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 > 2sigma(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
S	0.22668 (10)	0.81228 (8)	0.14051 (7)	0.0524 (3)
O1	0.2130 (3)	0.8490 (2)	0.2610 (2)	0.0726 (8)
O2	0.2305 (3)	0.6787 (2)	0.15228 (18)	0.0564 (7)
O3	0.3590 (3)	0.8450 (2)	0.0778 (2)	0.0685 (8)
C1	−0.3915 (5)	0.8728 (4)	−0.1679 (4)	0.0878 (14)
H1B	−0.3695	0.8862	−0.2499	0.132*
H1C	−0.4531	0.9345	−0.1399	0.132*
H1D	−0.4509	0.8038	−0.1630	0.132*
C2	−0.2361 (5)	0.8634 (3)	−0.0908 (3)	0.0590 (10)
C3	−0.0892 (5)	0.8731 (3)	−0.1392 (3)	0.0569 (9)
H3B	−0.0870	0.8893	−0.2207	0.068*
C4	0.0537 (4)	0.8594 (3)	−0.0705 (3)	0.0511 (8)
H4A	0.1509	0.8650	−0.1051	0.061*
C5	0.0493 (4)	0.8369 (3)	0.0522 (3)	0.0442 (8)
C6	−0.0958 (4)	0.8308 (3)	0.1034 (3)	0.0517 (9)
H6A	−0.0981	0.8178	0.1856	0.062*
C7	−0.2343 (5)	0.8439 (3)	0.0336 (3)	0.0623 (10)
H7A	−0.3310	0.8399	0.0690	0.075*
C8	0.2628 (5)	0.6142 (3)	0.0482 (3)	0.0662 (11)
H8A	0.3679	0.6333	0.0234	0.079*
H8B	0.1840	0.6316	−0.0178	0.079*
C9	0.2565 (6)	0.4960 (4)	0.0770 (4)	0.0717 (11)
F3	0.1153 (4)	0.4632 (3)	0.1101 (3)	0.1040 (9)
F2	0.3549 (4)	0.4617 (2)	0.1673 (3)	0.1064 (10)
F1	0.2812 (4)	0.4335 (3)	−0.0197 (3)	0.1119 (10)

	U11	U22	U33	U12	U13	U23
S	0.0482 (5)	0.0686 (6)	0.0399 (5)	0.0007 (4)	0.0000 (3)	−0.0052 (4)
O1	0.0794 (19)	0.095 (2)	0.0415 (14)	0.0052 (15)	−0.0036 (12)	−0.0168 (14)
O2	0.0625 (16)	0.0732 (17)	0.0339 (12)	0.0100 (12)	0.0057 (10)	0.0013 (11)
O3	0.0511 (15)	0.0831 (19)	0.0722 (17)	−0.0068 (13)	0.0115 (13)	0.0018 (15)
C1	0.075 (3)	0.096 (3)	0.087 (3)	0.005 (3)	−0.027 (2)	0.007 (3)
C2	0.063 (2)	0.056 (2)	0.055 (2)	0.0001 (18)	−0.0071 (18)	−0.0006 (18)
C3	0.070 (2)	0.070 (2)	0.0309 (17)	0.0066 (19)	0.0043 (16)	0.0094 (16)
C4	0.054 (2)	0.061 (2)	0.0397 (18)	0.0017 (16)	0.0090 (15)	0.0023 (16)
C5	0.0430 (18)	0.0482 (18)	0.0411 (17)	0.0026 (14)	0.0024 (13)	−0.0028 (14)
C6	0.051 (2)	0.063 (2)	0.0421 (18)	−0.0018 (16)	0.0120 (15)	0.0010 (16)
C7	0.052 (2)	0.069 (2)	0.066 (2)	−0.0010 (18)	0.0102 (18)	0.005 (2)
C8	0.079 (3)	0.070 (3)	0.052 (2)	0.007 (2)	0.0204 (19)	−0.0014 (19)
C9	0.079 (3)	0.068 (3)	0.067 (3)	−0.003 (2)	−0.005 (2)	−0.004 (2)
F3	0.096 (2)	0.110 (2)	0.106 (2)	−0.0209 (17)	0.0106 (16)	0.0062 (17)
F2	0.106 (2)	0.094 (2)	0.116 (2)	0.0091 (16)	−0.0117 (18)	0.0086 (17)
F1	0.132 (3)	0.096 (2)	0.109 (2)	0.0005 (18)	0.0163 (19)	−0.0149 (17)

S—O3	1.410 (3)	C4—C5	1.397 (4)
S—O1	1.425 (2)	C4—H4A	0.9300
S—O2	1.585 (3)	C5—C6	1.385 (4)
S—C5	1.740 (3)	C6—C7	1.354 (5)
O2—C8	1.432 (4)	C6—H6A	0.9300
C1—C2	1.506 (5)	C7—H7A	0.9300
C1—H1B	0.9600	C8—C9	1.437 (6)
C1—H1C	0.9600	C8—H8A	0.9700
C1—H1D	0.9600	C8—H8B	0.9700
C2—C3	1.387 (5)	C9—F2	1.314 (5)
C2—C7	1.404 (5)	C9—F3	1.325 (5)
C3—C4	1.379 (5)	C9—F1	1.336 (5)
C3—H3B	0.9300
O3—S—O1	120.54 (18)	C6—C5—C4	120.4 (3)
O3—S—O2	107.64 (15)	C6—C5—S	119.7 (2)
O1—S—O2	103.21 (15)	C4—C5—S	119.9 (3)
O3—S—C5	110.08 (16)	C7—C6—C5	119.8 (3)
O1—S—C5	110.68 (16)	C7—C6—H6A	120.1
O2—S—C5	102.95 (15)	C5—C6—H6A	120.1
C8—O2—S	117.9 (2)	C6—C7—C2	121.9 (3)
C2—C1—H1B	109.5	C6—C7—H7A	119.1
C2—C1—H1C	109.5	C2—C7—H7A	119.1
H1B—C1—H1C	109.5	O2—C8—C9	109.0 (3)
C2—C1—H1D	109.5	O2—C8—H8A	109.9
H1B—C1—H1D	109.5	C9—C8—H8A	109.9
H1C—C1—H1D	109.5	O2—C8—H8B	109.9
C3—C2—C7	117.2 (3)	C9—C8—H8B	109.9
C3—C2—C1	121.7 (4)	H8A—C8—H8B	108.3
C7—C2—C1	121.1 (4)	F2—C9—F3	102.5 (4)
C4—C3—C2	122.1 (3)	F2—C9—F1	108.7 (4)
C4—C3—H3B	118.9	F3—C9—F1	105.1 (4)
C2—C3—H3B	118.9	F2—C9—C8	116.1 (4)
C3—C4—C5	118.5 (3)	F3—C9—C8	113.4 (4)
C3—C4—H4A	120.7	F1—C9—C8	110.4 (4)
C5—C4—H4A	120.7
O3—S—O2—C8	−44.3 (3)	O1—S—C5—C4	149.6 (3)
O1—S—O2—C8	−172.8 (3)	O2—S—C5—C4	−100.7 (3)
C5—S—O2—C8	72.0 (3)	C4—C5—C6—C7	1.7 (5)
C7—C2—C3—C4	2.8 (6)	S—C5—C6—C7	−176.5 (3)
C1—C2—C3—C4	−176.9 (4)	C5—C6—C7—C2	0.2 (6)
C2—C3—C4—C5	−1.1 (6)	C3—C2—C7—C6	−2.4 (6)
C3—C4—C5—C6	−1.2 (5)	C1—C2—C7—C6	177.4 (4)
C3—C4—C5—S	176.9 (3)	S—O2—C8—C9	−178.5 (3)
O3—S—C5—C6	−168.1 (3)	O2—C8—C9—F2	−57.8 (5)
O1—S—C5—C6	−32.3 (3)	O2—C8—C9—F3	60.4 (5)
O2—S—C5—C6	77.4 (3)	O2—C8—C9—F1	178.0 (3)
O3—S—C5—C4	13.8 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4A···O3	0.93	2.59	2.938 (4)	103
C8—H8B···O1i	0.97	2.51	3.225 (4)	131

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C8—H8B⋯O1i	0.97	2.51	3.225 (4)	131

Symmetry code: (i) .