4-(2-Hy-droxy-phen-yl)-3,5-di-thia-hepta-ne-dioic acid.

In the crystal of the title compound, C11H12O5S2, mol-ecules are linked by O-H⋯O hydrogen bonds and C-H⋯O inter-actions, forming a three-dimensional network.

Related literature

For related structures, see: Guo et al. (2010 ▶); Yu et al. (2010 ▶); Rollas & Kucukguzel (2007 ▶). For bond-length data, see: Allen et al. (1987 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C11H12O5S2

M = 288.33

Triclinic,

a = 7.2465 (1) Å

b = 7.6533 (1) Å

c = 12.0141 (2) Å

α = 101.094 (2)°

β = 99.129 (1)°

γ = 102.390 (2)°

V = 624.57 (2) Å3

Z = 2

Mo Kα radiation

μ = 0.44 mm−1

T = 293 K

0.20 × 0.18 × 0.17 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T min = 0.916, T max = 0.929

2746 measured reflections

2180 independent reflections

1918 reflections with I > 2σ(I)

R int = 0.008

Refinement

R[F 2 > 2σ(F 2)] = 0.026

wR(F 2) = 0.073

S = 1.06

2180 reflections

175 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.24 e Å−3

Δρmin = −0.21 e Å−3

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT (Bruker, 2008 ▶); data reduction: SAINT; 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 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813012737/bt6906sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813012737/bt6906Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813012737/bt6906Isup3.cml

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

C11H12O5S2	Z = 2
Mr = 288.33	F(000) = 300
Triclinic, P1	Dx = 1.533 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.2465 (1) Å	Cell parameters from 1918 reflections
b = 7.6533 (1) Å	θ = 2.8–25.0°
c = 12.0141 (2) Å	µ = 0.44 mm−1
α = 101.094 (2)°	T = 293 K
β = 99.129 (1)°	Block, white
γ = 102.390 (2)°	0.20 × 0.18 × 0.17 mm
V = 624.57 (2) Å3

Bruker SMART APEXII CCD diffractometer	2180 independent reflections
Radiation source: fine-focus sealed tube	1918 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.008
ω and φ scans	θmax = 25.0°, θmin = 2.8°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −1→8
Tmin = 0.916, Tmax = 0.929	k = −9→9
2746 measured reflections	l = −14→14

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)] = 0.026	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.073	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ2(Fo2) + (0.0361P)2 + 0.2534P] where P = (Fo2 + 2Fc2)/3
2180 reflections	(Δ/σ)max < 0.001
175 parameters	Δρmax = 0.24 e Å−3
0 restraints	Δρmin = −0.21 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	1.00303 (6)	0.36671 (6)	0.31104 (4)	0.03515 (13)
S2	0.67356 (6)	0.52625 (6)	0.35266 (4)	0.03286 (13)
O1	0.9831 (2)	0.7027 (2)	0.09620 (11)	0.0426 (3)
H1	1.038 (4)	0.747 (3)	0.057 (2)	0.056 (7)*
O2	0.3103 (2)	0.5269 (2)	0.07080 (14)	0.0557 (4)
H2A	0.241 (4)	0.450 (3)	0.016 (2)	0.059 (7)*
O3	0.4267 (2)	0.29754 (18)	0.11941 (11)	0.0462 (3)
O4	0.8498 (3)	0.1453 (2)	0.06126 (12)	0.0639 (5)
O5	0.6463 (2)	−0.08304 (19)	0.10180 (13)	0.0520 (4)
H5A	0.628 (4)	−0.128 (3)	0.035 (2)	0.066 (8)*
C1	1.0698 (2)	0.7921 (2)	0.20917 (14)	0.0303 (4)
C2	1.2097 (3)	0.9569 (2)	0.23501 (17)	0.0395 (4)
H2	1.2477	1.0076	0.1753	0.047*
C3	1.2930 (3)	1.0461 (3)	0.34859 (18)	0.0443 (5)
H3	1.3869	1.1569	0.3655	0.053*
C4	1.2370 (3)	0.9711 (3)	0.43746 (17)	0.0476 (5)
H4	1.2925	1.0313	0.5143	0.057*
C5	1.0979 (3)	0.8059 (3)	0.41159 (16)	0.0411 (4)
H5	1.0612	0.7557	0.4717	0.049*
C6	1.0119 (2)	0.7133 (2)	0.29760 (14)	0.0281 (3)
C7	0.8675 (2)	0.5283 (2)	0.27182 (14)	0.0278 (3)
H7	0.8109	0.4901	0.1885	0.033*
C8	0.5047 (2)	0.5942 (2)	0.25420 (16)	0.0373 (4)
H8A	0.4038	0.6229	0.2932	0.045*
H8B	0.5710	0.7063	0.2362	0.045*
C9	0.4115 (2)	0.4540 (2)	0.14220 (16)	0.0354 (4)
C10	0.8202 (3)	0.1531 (2)	0.25863 (14)	0.0335 (4)
H10A	0.8600	0.0627	0.2971	0.040*
H10B	0.7017	0.1714	0.2811	0.040*
C11	0.7775 (3)	0.0751 (2)	0.12984 (15)	0.0357 (4)

	U11	U22	U33	U12	U13	U23
S1	0.0314 (2)	0.0288 (2)	0.0430 (3)	0.00619 (17)	0.00384 (18)	0.00810 (18)
S2	0.0303 (2)	0.0346 (2)	0.0324 (2)	0.00405 (17)	0.00923 (17)	0.00719 (17)
O1	0.0395 (7)	0.0544 (8)	0.0304 (7)	0.0001 (6)	0.0077 (6)	0.0144 (6)
O2	0.0534 (9)	0.0514 (9)	0.0531 (9)	0.0128 (7)	−0.0113 (7)	0.0093 (7)
O3	0.0524 (8)	0.0349 (7)	0.0429 (7)	0.0075 (6)	0.0017 (6)	0.0002 (6)
O4	0.0885 (12)	0.0598 (9)	0.0378 (8)	−0.0036 (8)	0.0236 (8)	0.0149 (7)
O5	0.0655 (10)	0.0373 (8)	0.0396 (8)	−0.0047 (7)	0.0083 (7)	−0.0009 (6)
C1	0.0290 (8)	0.0311 (8)	0.0333 (9)	0.0102 (7)	0.0081 (7)	0.0091 (7)
C2	0.0379 (10)	0.0351 (9)	0.0494 (11)	0.0060 (8)	0.0153 (8)	0.0174 (8)
C3	0.0370 (10)	0.0299 (9)	0.0593 (12)	−0.0030 (8)	0.0113 (9)	0.0062 (8)
C4	0.0450 (11)	0.0421 (11)	0.0408 (10)	−0.0055 (9)	0.0040 (9)	−0.0027 (8)
C5	0.0449 (10)	0.0406 (10)	0.0315 (9)	−0.0016 (8)	0.0081 (8)	0.0070 (8)
C6	0.0253 (8)	0.0258 (8)	0.0324 (8)	0.0047 (6)	0.0067 (6)	0.0065 (6)
C7	0.0283 (8)	0.0261 (8)	0.0276 (8)	0.0039 (7)	0.0059 (6)	0.0063 (6)
C8	0.0313 (9)	0.0318 (9)	0.0459 (10)	0.0087 (7)	0.0050 (8)	0.0038 (8)
C9	0.0272 (8)	0.0358 (10)	0.0405 (9)	0.0028 (7)	0.0070 (7)	0.0086 (8)
C10	0.0400 (10)	0.0255 (8)	0.0346 (9)	0.0043 (7)	0.0115 (7)	0.0079 (7)
C11	0.0422 (10)	0.0296 (9)	0.0369 (9)	0.0107 (8)	0.0103 (8)	0.0085 (7)

S1—C10	1.7984 (17)	C2—H2	0.9300
S1—C7	1.8207 (16)	C3—C4	1.382 (3)
S2—C8	1.7940 (18)	C3—H3	0.9300
S2—C7	1.8296 (16)	C4—C5	1.383 (3)
O1—C1	1.376 (2)	C4—H4	0.9300
O1—H1	0.75 (2)	C5—C6	1.390 (2)
O2—C9	1.321 (2)	C5—H5	0.9300
O2—H2A	0.81 (3)	C6—C7	1.513 (2)
O3—C9	1.209 (2)	C7—H7	0.9800
O4—C11	1.195 (2)	C8—C9	1.504 (2)
O5—C11	1.315 (2)	C8—H8A	0.9700
O5—H5A	0.79 (3)	C8—H8B	0.9700
C1—C2	1.384 (2)	C10—C11	1.503 (2)
C1—C6	1.396 (2)	C10—H10A	0.9700
C2—C3	1.377 (3)	C10—H10B	0.9700
C10—S1—C7	100.79 (8)	C6—C7—S2	113.81 (11)
C8—S2—C7	99.46 (8)	S1—C7—S2	109.04 (8)
C1—O1—H1	108.6 (19)	C6—C7—H7	109.2
C9—O2—H2A	112.0 (18)	S1—C7—H7	109.2
C11—O5—H5A	110.7 (19)	S2—C7—H7	109.2
O1—C1—C2	121.08 (15)	C9—C8—S2	115.36 (12)
O1—C1—C6	118.31 (15)	C9—C8—H8A	108.4
C2—C1—C6	120.61 (16)	S2—C8—H8A	108.4
C3—C2—C1	120.38 (17)	C9—C8—H8B	108.4
C3—C2—H2	119.8	S2—C8—H8B	108.4
C1—C2—H2	119.8	H8A—C8—H8B	107.5
C2—C3—C4	119.95 (17)	O3—C9—O2	124.33 (17)
C2—C3—H3	120.0	O3—C9—C8	125.59 (17)
C4—C3—H3	120.0	O2—C9—C8	110.08 (16)
C3—C4—C5	119.65 (18)	C11—C10—S1	115.58 (12)
C3—C4—H4	120.2	C11—C10—H10A	108.4
C5—C4—H4	120.2	S1—C10—H10A	108.4
C4—C5—C6	121.41 (17)	C11—C10—H10B	108.4
C4—C5—H5	119.3	S1—C10—H10B	108.4
C6—C5—H5	119.3	H10A—C10—H10B	107.4
C5—C6—C1	117.99 (15)	O4—C11—O5	123.98 (18)
C5—C6—C7	120.20 (15)	O4—C11—C10	125.68 (17)
C1—C6—C7	121.74 (14)	O5—C11—C10	110.34 (15)
C6—C7—S1	106.43 (11)
O1—C1—C2—C3	178.98 (17)	C5—C6—C7—S2	51.35 (19)
C6—C1—C2—C3	−0.4 (3)	C1—C6—C7—S2	−131.74 (14)
C1—C2—C3—C4	0.0 (3)	C10—S1—C7—C6	−172.98 (11)
C2—C3—C4—C5	0.3 (3)	C10—S1—C7—S2	63.85 (9)
C3—C4—C5—C6	−0.3 (3)	C8—S2—C7—C6	88.30 (13)
C4—C5—C6—C1	−0.1 (3)	C8—S2—C7—S1	−153.06 (9)
C4—C5—C6—C7	176.96 (17)	C7—S2—C8—C9	69.48 (14)
O1—C1—C6—C5	−178.99 (16)	S2—C8—C9—O3	7.7 (2)
C2—C1—C6—C5	0.4 (2)	S2—C8—C9—O2	−171.86 (13)
O1—C1—C6—C7	4.0 (2)	C7—S1—C10—C11	77.55 (14)
C2—C1—C6—C7	−176.55 (15)	S1—C10—C11—O4	−2.3 (3)
C5—C6—C7—S1	−68.78 (18)	S1—C10—C11—O5	178.19 (13)
C1—C6—C7—S1	108.13 (15)

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7···O1	0.98	2.39	2.846 (2)	108
C2—H2···O3i	0.93	2.58	3.395 (2)	146
O1—H1···O4ii	0.75 (2)	1.97 (2)	2.7143 (19)	173 (3)
C8—H8B···O5iii	0.97	2.53	3.429 (2)	154
O2—H2A···O1iv	0.81 (3)	1.92 (3)	2.706 (2)	163 (2)
O5—H5A···O3v	0.79 (3)	1.97 (3)	2.7459 (19)	165 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯O3i	0.93	2.58	3.395 (2)	146
O1—H1⋯O4ii	0.75 (2)	1.97 (2)	2.7143 (19)	173 (3)
C8—H8B⋯O5iii	0.97	2.53	3.429 (2)	154
O2—H2A⋯O1iv	0.81 (3)	1.92 (3)	2.706 (2)	163 (2)
O5—H5A⋯O3v	0.79 (3)	1.97 (3)	2.7459 (19)	165 (3)

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