2,2'-(p-Phenyl-enedithio)diacetic acid.

The complete molecule of the title compound, C(10)H(10)O(4)S(2), is generated by a crystallographic inversion centre. In the crystal, mol-ecules are linked into a one-dimensional chain by inter-molecular O-H⋯O hydrogen bonds.

Related literature

For rigid aromatic carboxylic acids, see: Hu et al. (2006 ▶). The title compound, a new flexible aromatic multicarboxyl­ate acid, was designed and synthesized on the basis of the 1,4-benzene­bisoxyacetate (Li et al., 2006 ▶) and phenyl­thio­acetate (Sandhu et al., 1991 ▶) analogues.

Experimental

Crystal data

C10H10O4S2

M = 258.30

Triclinic,

a = 5.5633 (4) Å

b = 6.9311 (5) Å

c = 7.6173 (6) Å

α = 79.809 (5)°

β = 70.738 (4)°

γ = 76.112 (4)°

V = 267.64 (3) Å3

Z = 1

Mo Kα radiation

μ = 0.49 mm−1

T = 296 K

0.47 × 0.30 × 0.20 mm

Data collection

Bruker APEXII diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.839, T max = 0.908

3837 measured reflections

1209 independent reflections

1136 reflections with I > 2σ(I)

R int = 0.016

Refinement

R[F 2 > 2σ(F 2)] = 0.027

wR(F 2) = 0.073

S = 1.09

1209 reflections

77 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.19 e Å−3

Δρmin = −0.26 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); 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/S1600536809015967/at2772sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809015967/at2772Isup2.hkl

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

C10H10O4S2	Z = 1
Mr = 258.30	F(000) = 134
Triclinic, P1	Dx = 1.603 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 5.5633 (4) Å	Cell parameters from 2874 reflections
b = 6.9311 (5) Å	θ = 2.9–27.6°
c = 7.6173 (6) Å	µ = 0.49 mm−1
α = 79.809 (5)°	T = 296 K
β = 70.738 (4)°	Block, colourless
γ = 76.112 (4)°	0.47 × 0.30 × 0.20 mm
V = 267.64 (3) Å3

Bruker APEXII diffractometer	1209 independent reflections
Radiation source: fine-focus sealed tube	1136 reflections with I > 2σ(I)
graphite	Rint = 0.016
ω scans	θmax = 27.6°, θmin = 2.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −7→7
Tmin = 0.839, Tmax = 0.908	k = −8→9
3837 measured reflections	l = −9→9

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)] = 0.027	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.073	H atoms treated by a mixture of independent and constrained refinement
S = 1.09	w = 1/[σ2(Fo2) + (0.0362P)2 + 0.0845P] where P = (Fo2 + 2Fc2)/3
1209 reflections	(Δ/σ)max < 0.001
77 parameters	Δρmax = 0.19 e Å−3
0 restraints	Δρmin = −0.26 e Å−3

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	0.66238 (6)	0.55947 (5)	0.67832 (5)	0.03597 (14)
O2	0.6441 (2)	0.17946 (15)	0.87948 (16)	0.0469 (3)
O1	0.2166 (2)	0.19194 (15)	0.97977 (16)	0.0425 (3)
H1	0.263 (4)	0.075 (4)	1.019 (3)	0.069 (7)*
C1	0.5592 (3)	0.80504 (18)	0.58268 (18)	0.0294 (3)
C2	0.3044 (3)	0.9090 (2)	0.6244 (2)	0.0396 (3)
H2A	0.1718	0.8488	0.7077	0.048*
C3	0.2472 (3)	1.1024 (2)	0.5422 (2)	0.0390 (3)
H3A	0.0759	1.1712	0.5713	0.047*
C4	0.3615 (3)	0.47918 (19)	0.80700 (19)	0.0327 (3)
H4A	0.2621	0.5652	0.9046	0.039*
H4B	0.2589	0.4866	0.7240	0.039*
C5	0.4234 (3)	0.26763 (19)	0.89175 (19)	0.0327 (3)

	U11	U22	U33	U12	U13	U23
S1	0.0319 (2)	0.02282 (19)	0.0434 (2)	−0.00331 (13)	−0.00692 (15)	0.01037 (13)
O2	0.0351 (6)	0.0282 (5)	0.0625 (7)	−0.0045 (4)	−0.0070 (5)	0.0159 (5)
O1	0.0346 (5)	0.0263 (5)	0.0558 (7)	−0.0073 (4)	−0.0062 (5)	0.0111 (5)
C1	0.0329 (6)	0.0197 (6)	0.0314 (6)	−0.0045 (5)	−0.0078 (5)	0.0035 (5)
C2	0.0305 (7)	0.0276 (7)	0.0469 (8)	−0.0061 (5)	−0.0006 (6)	0.0106 (6)
C3	0.0278 (6)	0.0274 (7)	0.0494 (8)	−0.0018 (5)	−0.0038 (6)	0.0075 (6)
C4	0.0327 (7)	0.0227 (6)	0.0361 (7)	−0.0042 (5)	−0.0071 (5)	0.0060 (5)
C5	0.0351 (7)	0.0241 (6)	0.0337 (7)	−0.0061 (5)	−0.0065 (5)	0.0031 (5)

S1—C1	1.7679 (12)	C2—C3	1.3860 (19)
S1—C4	1.8010 (14)	C2—H2A	0.9300
O2—C5	1.2139 (18)	C3—C1i	1.3843 (19)
O1—C5	1.3058 (17)	C3—H3A	0.9300
O1—H1	0.82 (2)	C4—C5	1.5015 (17)
C1—C3i	1.3843 (19)	C4—H4A	0.9700
C1—C2	1.3866 (19)	C4—H4B	0.9700
C1—S1—C4	103.14 (6)	C2—C3—H3A	119.4
C5—O1—H1	108.3 (16)	C5—C4—S1	108.38 (9)
C3i—C1—C2	118.87 (12)	C5—C4—H4A	110.0
C3i—C1—S1	115.93 (10)	S1—C4—H4A	110.0
C2—C1—S1	125.20 (10)	C5—C4—H4B	110.0
C3—C2—C1	120.01 (13)	S1—C4—H4B	110.0
C3—C2—H2A	120.0	H4A—C4—H4B	108.4
C1—C2—H2A	120.0	O2—C5—O1	124.48 (12)
C1i—C3—C2	121.12 (13)	O2—C5—C4	122.57 (12)
C1i—C3—H3A	119.4	O1—C5—C4	112.95 (12)
C4—S1—C1—C3i	−173.10 (11)	C1—C2—C3—C1i	0.2 (3)
C4—S1—C1—C2	7.47 (15)	C1—S1—C4—C5	178.43 (9)
C3i—C1—C2—C3	−0.2 (3)	S1—C4—C5—O2	4.17 (19)
S1—C1—C2—C3	179.18 (12)	S1—C4—C5—O1	−176.44 (10)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2ii	0.82 (2)	1.82 (2)	2.6440 (14)	177 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O2i	0.82 (2)	1.82 (2)	2.6440 (14)	177 (2)

Symmetry code: (i) .