2,2'-(Carbono-thio-yldisulfanedi-yl)bis-(2-methyl-propanoic acid).

The mol-ecular structure of the title compound, C9H14O4S3, exhibits intra-molecular C-H⋯S hydrogen bonds. In the crystal, pairs of O-H⋯O hydrogen bonds lead to the formation of centrosymmetric dimers, which are in turn connected by weak C-H⋯O inter-actions. The combination of these inter-actions generates edge-fused R 2 (2)(8) and R 2 (2)(20) rings running along [211].

Related literature

For pharmaceutical properties of tri­thio­carbonates, see: Dehmel et al. (2007 ▶). For tri­thio­carbonates as inter­mediates in organic synthesis, see: Metzner (1996 ▶). For the control of polymerization reactions of tri­thio­carbonates, see: Harrisson & Wooley (2005 ▶); Bilalis et al. (2006 ▶); Millard et al. (2006 ▶). For radical polymerization with RAFT reactions, see: Moad et al. (2005 ▶). For related structures, see: El-khateeb & Roller (2007 ▶). For hydrogen bonding, see: Nardelli (1995 ▶). For graph-set motifs, see: Etter (1990 ▶). For the synthesis, see: Lai et al. (2002 ▶).

Experimental

Crystal data

C9H14O4S3

M = 282.41

Monoclinic,

a = 10.4044 (2) Å

b = 10.4947 (2) Å

c = 13.7744 (3) Å

β = 117.363 (1)°

V = 1335.76 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.55 mm−1

T = 295 K

0.34 × 0.29 × 0.23 mm

Data collection

Nonius KappaCCD diffractometer

5423 measured reflections

2825 independent reflections

2273 reflections with I > 2σ(I)

R int = 0.022

Refinement

R[F 2 > 2σ(F 2)] = 0.031

wR(F 2) = 0.084

S = 1.05

2825 reflections

151 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.24 e Å−3

Δρmin = −0.24 e Å−3

Data collection: COLLECT (Nonius, 2000 ▶); cell refinement: SCALEPACK (Otwinowski & Minor, 1997 ▶); data reduction: DENZO (Otwinowski & Minor, 1997 ▶) and SCALEPACK; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶) and Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: WinGX (Farrugia, 2012 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813010179/zq2200sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813010179/zq2200Isup2.hkl

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

C9H14O4S3	F(000) = 592
Mr = 282.41	Dx = 1.404 Mg m−3
Monoclinic, P21/c	Melting point < 447(1) K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 10.4044 (2) Å	Cell parameters from 4448 reflections
b = 10.4947 (2) Å	θ = 2.9–26.4°
c = 13.7744 (3) Å	µ = 0.55 mm−1
β = 117.363 (1)°	T = 295 K
V = 1335.76 (5) Å3	Block, colourless
Z = 4	0.34 × 0.29 × 0.23 mm

Nonius KappaCCD diffractometer	2273 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.022
Graphite monochromator	θmax = 26.7°, θmin = 2.9°
CCD rotation images, thick slices scans	h = −13→13
5423 measured reflections	k = −12→13
2825 independent reflections	l = −17→17

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)] = 0.031	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.084	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.040P)2 + 0.2778P] where P = (Fo2 + 2Fc2)/3
2825 reflections	(Δ/σ)max < 0.001
151 parameters	Δρmax = 0.24 e Å−3
1 restraint	Δρmin = −0.24 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	0.10424 (5)	0.69853 (5)	0.04522 (4)	0.05515 (16)
S2	0.12916 (4)	0.78396 (4)	0.26245 (3)	0.04274 (14)
S3	0.37515 (4)	0.67719 (5)	0.26019 (3)	0.04675 (14)
O1	0.33615 (14)	0.42986 (12)	0.13674 (9)	0.0503 (3)
H1	0.3078	0.3696	0.0941	0.075*
O2	0.34295 (12)	0.52637 (11)	−0.00505 (9)	0.0455 (3)
O3	−0.14354 (12)	0.62947 (11)	0.14151 (9)	0.0445 (3)
H3	−0.2066	0.5824	0.0979	0.067*
O4	−0.23775 (13)	0.76463 (12)	0.00151 (9)	0.0483 (3)
C1	0.19482 (17)	0.71974 (15)	0.17693 (13)	0.0381 (4)
C2	0.45203 (17)	0.63284 (17)	0.16830 (13)	0.0419 (4)
C3	−0.05423 (17)	0.84249 (15)	0.17297 (12)	0.0366 (3)
C4	0.36796 (16)	0.52512 (16)	0.09110 (13)	0.0383 (4)
C5	0.4659 (2)	0.74751 (19)	0.10631 (17)	0.0558 (5)
H5A	0.3714	0.7811	0.0598	0.084*
H5B	0.5115	0.7220	0.0627	0.084*
H5C	0.5234	0.8118	0.1574	0.084*
C6	0.60223 (18)	0.5785 (2)	0.24740 (15)	0.0561 (5)
H6A	0.6495	0.5481	0.2063	0.084*
H6B	0.5906	0.5095	0.2884	0.084*
H6C	0.6598	0.6443	0.2966	0.084*
C7	−0.15123 (16)	0.74014 (15)	0.09617 (13)	0.0361 (3)
C8	−0.0491 (2)	0.96101 (17)	0.11115 (16)	0.0554 (5)
H8A	−0.1453	0.9939	0.0695	0.083*
H8B	−0.0093	0.9394	0.0627	0.083*
H8C	0.0105	1.0244	0.1622	0.083*
C9	−0.11435 (18)	0.87531 (18)	0.25362 (14)	0.0477 (4)
H9A	−0.1148	0.8001	0.2931	0.072*
H9B	−0.2113	0.9072	0.2138	0.072*
H9C	−0.0544	0.9390	0.3041	0.072*

	U11	U22	U33	U12	U13	U23
S1	0.0460 (3)	0.0823 (4)	0.0357 (2)	0.0060 (2)	0.0175 (2)	−0.0126 (2)
S2	0.0379 (2)	0.0577 (3)	0.0339 (2)	−0.00402 (18)	0.01772 (18)	−0.01094 (18)
S3	0.0382 (2)	0.0629 (3)	0.0380 (2)	−0.00095 (19)	0.01655 (19)	−0.0126 (2)
O1	0.0637 (8)	0.0455 (7)	0.0407 (6)	−0.0137 (6)	0.0231 (6)	−0.0044 (5)
O2	0.0509 (7)	0.0515 (7)	0.0396 (6)	−0.0110 (6)	0.0254 (5)	−0.0085 (5)
O3	0.0501 (7)	0.0375 (7)	0.0386 (6)	−0.0082 (5)	0.0140 (5)	0.0010 (5)
O4	0.0501 (7)	0.0431 (7)	0.0375 (7)	0.0021 (5)	0.0079 (6)	0.0026 (5)
C1	0.0384 (8)	0.0397 (9)	0.0386 (7)	−0.0071 (7)	0.0197 (7)	−0.0083 (7)
C2	0.0368 (8)	0.0488 (10)	0.0438 (9)	−0.0072 (7)	0.0217 (7)	−0.0121 (8)
C3	0.0413 (8)	0.0358 (9)	0.0351 (8)	−0.0033 (7)	0.0195 (7)	−0.0046 (6)
C4	0.0327 (8)	0.0432 (9)	0.0411 (9)	−0.0018 (7)	0.0186 (7)	−0.0047 (7)
C5	0.0592 (12)	0.0519 (11)	0.0653 (12)	−0.0185 (9)	0.0363 (10)	−0.0126 (9)
C6	0.0375 (9)	0.0708 (13)	0.0572 (11)	−0.0017 (9)	0.0192 (8)	−0.0141 (10)
C7	0.0369 (8)	0.0361 (9)	0.0369 (9)	0.0004 (7)	0.0183 (7)	−0.0014 (7)
C8	0.0770 (13)	0.0376 (10)	0.0559 (11)	−0.0077 (9)	0.0342 (10)	−0.0017 (8)
C9	0.0470 (10)	0.0541 (11)	0.0478 (10)	−0.0012 (8)	0.0268 (8)	−0.0115 (8)

S1—C1	1.6301 (16)	C3—C8	1.522 (2)
S2—C1	1.7460 (16)	C3—C9	1.544 (2)
S2—C3	1.8372 (16)	C5—H5A	0.9600
S3—C1	1.7484 (17)	C5—H5B	0.9600
S3—C2	1.8410 (16)	C5—H5C	0.9600
O1—C4	1.302 (2)	C6—H6A	0.9600
O1—H1	0.8200	C6—H6B	0.9600
O2—C4	1.2268 (18)	C6—H6C	0.9600
O3—C7	1.3037 (19)	C8—H8A	0.9600
O3—H3	0.8200	C8—H8B	0.9600
O4—C7	1.2238 (18)	C8—H8C	0.9600
C2—C5	1.520 (3)	C9—H9A	0.9600
C2—C4	1.523 (2)	C9—H9B	0.9600
C2—C6	1.546 (2)	C9—H9C	0.9600
C3—C7	1.520 (2)
C1—S2—C3	106.51 (7)	C2—C5—H5C	109.5
C1—S3—C2	106.73 (7)	H5A—C5—H5C	109.5
C4—O1—H1	109.5	H5B—C5—H5C	109.5
C7—O3—H3	109.5	C2—C6—H6A	109.5
S1—C1—S2	126.75 (10)	C2—C6—H6B	109.5
S1—C1—S3	126.32 (9)	H6A—C6—H6B	109.5
S2—C1—S3	106.90 (9)	C2—C6—H6C	109.5
C5—C2—C4	111.58 (14)	H6A—C6—H6C	109.5
C5—C2—C6	111.21 (15)	H6B—C6—H6C	109.5
C4—C2—C6	106.77 (14)	O4—C7—O3	123.42 (15)
C5—C2—S3	111.67 (12)	O4—C7—C3	121.41 (15)
C4—C2—S3	112.10 (11)	O3—C7—C3	114.91 (13)
C6—C2—S3	103.10 (11)	C3—C8—H8A	109.5
C7—C3—C8	111.77 (14)	C3—C8—H8B	109.5
C7—C3—C9	107.43 (13)	H8A—C8—H8B	109.5
C8—C3—C9	110.50 (14)	C3—C8—H8C	109.5
C7—C3—S2	112.54 (11)	H8A—C8—H8C	109.5
C8—C3—S2	110.85 (12)	H8B—C8—H8C	109.5
C9—C3—S2	103.37 (11)	C3—C9—H9A	109.5
O2—C4—O1	123.69 (15)	C3—C9—H9B	109.5
O2—C4—C2	120.97 (15)	H9A—C9—H9B	109.5
O1—C4—C2	115.13 (13)	C3—C9—H9C	109.5
C2—C5—H5A	109.5	H9A—C9—H9C	109.5
C2—C5—H5B	109.5	H9B—C9—H9C	109.5
H5A—C5—H5B	109.5
S1—S1—C1—S2	0.00 (2)	C1—S2—C3—C9	170.36 (11)
S1—S1—C1—S3	0.00 (5)	C5—C2—C4—O2	13.2 (2)
C3—S2—C1—S1	−7.38 (14)	C6—C2—C4—O2	−108.50 (17)
C3—S2—C1—S1	−7.38 (14)	S3—C2—C4—O2	139.30 (13)
C3—S2—C1—S3	174.63 (8)	C5—C2—C4—O1	−171.90 (14)
C2—S3—C1—S1	10.52 (14)	C6—C2—C4—O1	66.40 (17)
C2—S3—C1—S1	10.52 (14)	S3—C2—C4—O1	−45.80 (17)
C2—S3—C1—S2	−171.47 (8)	C8—C3—C7—O4	−15.6 (2)
C1—S3—C2—C5	68.46 (14)	C9—C3—C7—O4	105.74 (17)
C1—S3—C2—C4	−57.59 (14)	S2—C3—C7—O4	−141.14 (13)
C1—S3—C2—C6	−172.07 (12)	C8—C3—C7—O3	170.06 (14)
C1—S2—C3—C7	54.77 (13)	C9—C3—C7—O3	−68.56 (18)
C1—S2—C3—C8	−71.23 (13)	S2—C3—C7—O3	44.56 (16)

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8B···S1	0.96	2.85	3.506 (2)	127
C5—H5A···S1	0.96	2.83	3.4955 (19)	127
O1—H1···O4i	0.82	1.84	2.6549 (17)	178
O3—H3···O2i	0.82	1.81	2.6321 (15)	178
C6—H6C···O4ii	0.96	2.69	3.518 (2)	144

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C8—H8B⋯S1	0.96	2.85	3.506 (2)	127
C5—H5A⋯S1	0.96	2.83	3.4955 (19)	127
O1—H1⋯O4i	0.82	1.84	2.6549 (17)	178
O3—H3⋯O2i	0.82	1.81	2.6321 (15)	178
C6—H6C⋯O4ii	0.96	2.69	3.518 (2)	144

Symmetry codes: (i) ; (ii) .