2-Methyl­sulfonyl-4-(trifluoro­meth­yl)benzoic acid

Lin-Shan Yao; Bo We; Jin-Sheng Gao

doi:10.1107/S160053681202243X

. 2012 May 23;68(Pt 6):o1856. doi: 10.1107/S160053681202243X

2-Methylsulfonyl-4-(trifluoromethyl)benzoic acid

Lin-Shan Yao ^a, Bo We ^a, Jin-Sheng Gao ^a,^*

PMCID: PMC3379423 PMID: 22719621

Abstract

In the title molecule, C₉H₇F₃O₄S, the S and the methyl C atoms of the methylsulfonyl group deviate from the benzene ring plane by 0.185 (2) and −1.394 (3) Å, respectively. In the crystal, O—H⋯O hydrogen bonds link the molecules into chains along [201]. Weak C—H⋯O interactions further link these chains into layers parallel to the ac plane.

Related literature

For details of the synthesis, see: Cain et al. (1998 ▶). graphic file with name e-68-o1856-scheme1.jpg

Experimental

Crystal data

C₉H₇F₃O₄S
M _r = 268.21
Monoclinic,
a = 5.0804 (10) Å
b = 17.345 (4) Å
c = 11.576 (2) Å
β = 95.41 (3)°
V = 1015.6 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.36 mm⁻¹
T = 293 K
0.39 × 0.32 × 0.22 mm

Data collection

Rigaku R-AXIS RAPID diffractometer
Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ▶) T _min = 0.871, T _max = 0.926
9132 measured reflections
2250 independent reflections
1879 reflections with I > 2σ(I)
R _int = 0.029

Refinement

R[F ² > 2σ(F ²)] = 0.044
wR(F ²) = 0.123
S = 1.11
2250 reflections
158 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.39 e Å⁻³
Δρ_min = −0.38 e Å⁻³

Data collection: RAPID-AUTO (Rigaku, 1998 ▶); cell refinement: RAPID-AUTO; data reduction: CrystalClear (Rigaku/MSC, 2002 ▶); 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: SHELXL97.

Supplementary Material

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S160053681202243X/cv5300sup1.cif

e-68-o1856-sup1.cif^{(18.9KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681202243X/cv5300Isup2.hkl

e-68-o1856-Isup2.hkl^{(110.6KB, hkl)}

Supplementary material file. DOI: 10.1107/S160053681202243X/cv5300Isup3.cml

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

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯O4ⁱ	0.82 (1)	1.92 (1)	2.725 (3)	169 (4)
C9—H9B⋯O3ⁱⁱ	0.96	2.35	3.208 (3)	148

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Symmetry codes: (i) Inline graphic ; (ii) .

Acknowledgments

The authors thank the Project of Innovation Service Platform of Heilongjiang Province (grant No. PG09J001) and Heilongjiang University for support.

supplementary crystallographic information

Comment

The title compound, (I), is a intermediate in the synthesis of sulfonylurea herbicides developed and produced by E. I. du Pont de Nemours and Company. Herein, we report its crystal structure.

In (I) (Fig. 1), the S and the methyl C atoms of the methylsulfonyl group deviate from the benzene ring plane at 0.185 (2) and -1.394 (3) Å, respectively. Intermoleculear O—H···O hydrogen bonds (Table 1) link the molecules into chains along [201] (Fig. 2), and weak C—H···O interactions (Table 1) link further these chains into layers parallel to ac plane.

Experimental

The title compound was prepared by the reaction of 2-(methylsulphenyl)-4-trifluoromethylbenzoic acid and hydrogen peroxide in acetic acid at 10 ° (Cain et al., 1998). A colourless crystal suitable for single-crystal X-ray diffraction was obtained by the recrystallization from dichloromethane.