[4-(Methyl-sulfon-yl)phen-yl]acetic acid.

In the crystal structure of the title compound, C(9)H(10)O(4)S, centrosymmetrically related mol-ecules are linked into dimers by inter-molecular O-H⋯O hydrogen bonds. Unconventional C-H⋯O hydrogen-bond inter-actions are also present, connecting dimers into a three-dimensional network.

Related literature

For general background on the properties of the title compound and its derivatives, see: Parimalan et al. (2008 ▶); Giridhar et al. (2006 ▶). For the crystal structures of related compounds, see: Guo & Yuan (2006 ▶); Hartung et al. (2004 ▶); Hodgson & Asplund (1991 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C9H10O4S

M = 214.23

Monoclinic,

a = 19.086 (7) Å

b = 4.9711 (18) Å

c = 10.724 (4) Å

β = 106.102 (6)°

V = 977.5 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.32 mm−1

T = 298 (2) K

0.52 × 0.30 × 0.24 mm

Data collection

Bruker SMART APEX area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2004 ▶) T min = 0.853, T max = 0.928

4462 measured reflections

1638 independent reflections

1502 reflections with I > 2σ(I)

R int = 0.019

Refinement

R[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.140

S = 1.11

1638 reflections

129 parameters

H-atom parameters constrained

Δρmax = 0.24 e Å−3

Δρmin = −0.43 e Å−3

Data collection: SMART (Bruker, 2002 ▶); cell refinement: SAINT (Bruker, 2002 ▶); data reduction: SAINT; 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.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053680803660X/rz2263sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680803660X/rz2263Isup2.hkl

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

C9H10O4S	F000 = 448
Mr = 214.23	Dx = 1.456 Mg m−3
Monoclinic, P21/c	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2824 reflections
a = 19.086 (7) Å	θ = 2.2–27.7º
b = 4.9711 (18) Å	µ = 0.32 mm−1
c = 10.724 (4) Å	T = 298 (2) K
β = 106.102 (6)º	Block, colourless
V = 977.5 (6) Å3	0.52 × 0.30 × 0.24 mm
Z = 4

Bruker APEX area-detector diffractometer	1638 independent reflections
Radiation source: fine-focus sealed tube	1502 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.020
T = 298(2) K	θmax = 25.0º
φ and ω scans	θmin = 1.1º
Absorption correction: Multi-scan(SADABS; Sheldrick, 2004)	h = −22→22
Tmin = 0.853, Tmax = 0.928	k = −5→5
4462 measured reflections	l = −11→12

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.048	H-atom parameters constrained
wR(F2) = 0.140	w = 1/[σ2(Fo2) + (0.0848P)2 + 0.3788P] where P = (Fo2 + 2Fc2)/3
S = 1.11	(Δ/σ)max = 0.001
1638 reflections	Δρmax = 0.24 e Å−3
129 parameters	Δρmin = −0.43 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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
S1	0.38734 (3)	0.64558 (12)	1.01463 (5)	0.0408 (3)
O1	0.41630 (11)	0.5716 (4)	0.90951 (18)	0.0609 (6)
O2	0.36962 (11)	0.4358 (4)	1.09321 (19)	0.0575 (5)
O3	0.07977 (10)	0.9489 (5)	0.6087 (2)	0.0694 (7)
O4	0.00360 (10)	1.2830 (5)	0.6090 (2)	0.0677 (6)
H4	−0.0197	1.2097	0.5418	0.102*
C1	0.44823 (14)	0.8670 (5)	1.1176 (3)	0.0487 (6)
H1A	0.4947	0.7807	1.1501	0.073*
H1B	0.4296	0.9159	1.1889	0.073*
H1C	0.4537	1.0256	1.0701	0.073*
C2	0.30708 (12)	0.8358 (4)	0.9483 (2)	0.0361 (5)
C3	0.30404 (13)	1.0060 (5)	0.8448 (2)	0.0425 (6)
H3	0.3440	1.0226	0.8117	0.051*
C4	0.24133 (14)	1.1507 (5)	0.7913 (2)	0.0481 (6)
H4A	0.2393	1.2662	0.7221	0.058*
C5	0.18090 (13)	1.1260 (5)	0.8396 (2)	0.0434 (6)
C6	0.18554 (13)	0.9570 (6)	0.9437 (3)	0.0491 (6)
H6	0.1458	0.9413	0.9775	0.059*
C7	0.24791 (13)	0.8111 (5)	0.9986 (2)	0.0457 (6)
H7	0.2502	0.6975	1.0685	0.055*
C8	0.11162 (14)	1.2792 (6)	0.7781 (3)	0.0571 (7)
H8A	0.0838	1.2955	0.8410	0.069*
H8B	0.1244	1.4594	0.7574	0.069*
C9	0.06426 (13)	1.1525 (5)	0.6574 (3)	0.0451 (6)

	U11	U22	U33	U12	U13	U23
S1	0.0481 (4)	0.0392 (4)	0.0331 (4)	0.0129 (2)	0.0079 (3)	−0.0027 (2)
O1	0.0635 (11)	0.0752 (13)	0.0449 (11)	0.0256 (10)	0.0164 (9)	−0.0110 (10)
O2	0.0767 (13)	0.0387 (10)	0.0564 (12)	0.0120 (9)	0.0176 (10)	0.0082 (8)
O3	0.0530 (11)	0.0703 (14)	0.0648 (13)	0.0194 (10)	−0.0170 (9)	−0.0235 (11)
O4	0.0509 (11)	0.0665 (13)	0.0667 (14)	0.0203 (10)	−0.0155 (9)	−0.0117 (11)
C1	0.0470 (13)	0.0516 (15)	0.0415 (14)	0.0117 (11)	0.0024 (11)	−0.0031 (11)
C2	0.0381 (11)	0.0374 (12)	0.0294 (11)	0.0036 (9)	0.0038 (9)	−0.0038 (9)
C3	0.0420 (12)	0.0509 (14)	0.0338 (13)	0.0017 (10)	0.0090 (10)	0.0022 (10)
C4	0.0541 (14)	0.0492 (15)	0.0349 (13)	0.0037 (11)	0.0022 (11)	0.0066 (10)
C5	0.0387 (12)	0.0450 (14)	0.0378 (13)	0.0031 (10)	−0.0038 (10)	−0.0110 (10)
C6	0.0386 (12)	0.0585 (15)	0.0499 (15)	0.0000 (11)	0.0116 (11)	−0.0038 (13)
C7	0.0486 (13)	0.0489 (14)	0.0401 (14)	0.0013 (11)	0.0132 (11)	0.0062 (11)
C8	0.0487 (14)	0.0545 (16)	0.0557 (17)	0.0130 (13)	−0.0061 (12)	−0.0132 (13)
C9	0.0364 (12)	0.0471 (15)	0.0449 (14)	0.0044 (10)	−0.0001 (10)	0.0002 (11)

S1—O1	1.4342 (19)	C3—C4	1.378 (4)
S1—O2	1.439 (2)	C3—H3	0.9300
S1—C1	1.752 (3)	C4—C5	1.394 (4)
S1—C2	1.773 (2)	C4—H4A	0.9300
O3—C9	1.212 (3)	C5—C6	1.380 (4)
O4—C9	1.303 (3)	C5—C8	1.510 (3)
O4—H4	0.8200	C6—C7	1.379 (4)
C1—H1A	0.9600	C6—H6	0.9300
C1—H1B	0.9600	C7—H7	0.9300
C1—H1C	0.9600	C8—C9	1.497 (4)
C2—C3	1.384 (3)	C8—H8A	0.9700
C2—C7	1.386 (3)	C8—H8B	0.9700
O1—S1—O2	118.61 (12)	C3—C4—H4A	119.6
O1—S1—C1	108.87 (13)	C5—C4—H4A	119.6
O2—S1—C1	107.99 (13)	C6—C5—C4	118.7 (2)
O1—S1—C2	107.44 (11)	C6—C5—C8	120.8 (2)
O2—S1—C2	107.72 (12)	C4—C5—C8	120.5 (2)
C1—S1—C2	105.44 (11)	C7—C6—C5	121.3 (2)
C9—O4—H4	109.5	C7—C6—H6	119.3
S1—C1—H1A	109.5	C5—C6—H6	119.3
S1—C1—H1B	109.5	C6—C7—C2	119.2 (2)
H1A—C1—H1B	109.5	C6—C7—H7	120.4
S1—C1—H1C	109.5	C2—C7—H7	120.4
H1A—C1—H1C	109.5	C9—C8—C5	114.3 (2)
H1B—C1—H1C	109.5	C9—C8—H8A	108.7
C3—C2—C7	120.6 (2)	C5—C8—H8A	108.7
C3—C2—S1	119.18 (17)	C9—C8—H8B	108.7
C7—C2—S1	120.22 (18)	C5—C8—H8B	108.7
C4—C3—C2	119.5 (2)	H8A—C8—H8B	107.6
C4—C3—H3	120.3	O3—C9—O4	122.7 (2)
C2—C3—H3	120.3	O3—C9—C8	124.2 (2)
C3—C4—C5	120.8 (2)	O4—C9—C8	113.0 (2)
O1—S1—C2—C3	−35.3 (2)	C3—C4—C5—C8	−178.3 (2)
O2—S1—C2—C3	−164.15 (19)	C4—C5—C6—C7	−1.0 (4)
C1—S1—C2—C3	80.7 (2)	C8—C5—C6—C7	178.4 (2)
O1—S1—C2—C7	143.9 (2)	C5—C6—C7—C2	0.2 (4)
O2—S1—C2—C7	15.0 (2)	C3—C2—C7—C6	0.5 (4)
C1—S1—C2—C7	−100.1 (2)	S1—C2—C7—C6	−178.71 (19)
C7—C2—C3—C4	−0.3 (4)	C6—C5—C8—C9	−98.9 (3)
S1—C2—C3—C4	178.84 (19)	C4—C5—C8—C9	80.5 (3)
C2—C3—C4—C5	−0.4 (4)	C5—C8—C9—O3	−2.1 (4)
C3—C4—C5—C6	1.1 (4)	C5—C8—C9—O4	177.6 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4···O3i	0.82	1.87	2.693 (3)	175
C3—H3···O2ii	0.93	2.53	3.287 (3)	139
C1—H1B···O1iii	0.96	2.45	3.365 (4)	160

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O4—H4⋯O3i	0.82	1.87	2.693 (3)	175
C3—H3⋯O2ii	0.93	2.53	3.287 (3)	139
C1—H1B⋯O1iii	0.96	2.45	3.365 (4)	160

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