4-(1,3-Thia-zolidin-2-yl)phenol.

In the title compound, C(9)H(11)NOS, the thia-zolidinyl ring is almost perpendicular to the phenyl ring with N-C-C-C torsion angles of 71.7 (2) and 107.1 (2)°. In the crystal, mol-ecules are connected via N-H⋯O and O-H⋯N hydrogen bonds, forming layers.

Related literature

For the cyclization of 2-amino-ethanthiol Schiff bases, see: Al-Sayyab et al. (1968 ▶); Stacy & Strong (1967 ▶); Thompson & Busch (1964 ▶).

Experimental

Crystal data

C9H11NOS

M = 181.25

Orthorhombic,

a = 12.3638 (6) Å

b = 8.9683 (5) Å

c = 15.8249 (8) Å

V = 1754.7 (2) Å3

Z = 8

Mo Kα radiation

μ = 0.32 mm−1

T = 173 K

0.47 × 0.45 × 0.16 mm

Data collection

Bruker SMART 1000 CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2004 ▶) T min = 0.865, T max = 0.951

9635 measured reflections

1919 independent reflections

1615 reflections with I > 2σ(I)

R int = 0.022

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.105

S = 1.07

1919 reflections

115 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.37 e Å−3

Δρmin = −0.17 e Å−3

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT-Plus (Bruker, 2003 ▶); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809042135/im2144sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809042135/im2144Isup2.hkl

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

C9H11NOS	F(000) = 768
Mr = 181.25	Dx = 1.372 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 4931 reflections
a = 12.3638 (6) Å	θ = 2.6–27.0°
b = 8.9683 (5) Å	µ = 0.32 mm−1
c = 15.8249 (8) Å	T = 173 K
V = 1754.7 (2) Å3	Block, colorless
Z = 8	0.47 × 0.45 × 0.16 mm

Bruker SMART 1000 CCD diffractometer	1919 independent reflections
Radiation source: fine-focus sealed tube	1615 reflections with I > 2σ(I)
graphite	Rint = 0.022
ω scans	θmax = 27.0°, θmin = 2.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	h = −15→15
Tmin = 0.865, Tmax = 0.951	k = −11→8
9635 measured reflections	l = −20→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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.105	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	w = 1/[σ2(Fo2) + (0.0611P)2 + 0.7197P] where P = (Fo2 + 2Fc2)/3
1919 reflections	(Δ/σ)max < 0.001
115 parameters	Δρmax = 0.37 e Å−3
0 restraints	Δρmin = −0.17 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	0.47979 (3)	0.18010 (5)	0.70817 (2)	0.02679 (16)
C1	0.27121 (14)	0.1895 (2)	0.74816 (11)	0.0355 (4)
H1B	0.2501	0.2924	0.7327	0.043*
H1C	0.2046	0.1288	0.7530	0.043*
C2	0.34426 (15)	0.1245 (3)	0.67981 (12)	0.0417 (5)
H2A	0.3245	0.1646	0.6236	0.050*
H2B	0.3381	0.0145	0.6783	0.050*
C3	0.43704 (12)	0.24880 (18)	0.81446 (9)	0.0217 (3)
H3	0.4323	0.3600	0.8119	0.026*
C4	0.51646 (12)	0.20804 (17)	0.88292 (9)	0.0209 (3)
C5	0.55139 (13)	0.31669 (17)	0.93977 (10)	0.0235 (3)
H5	0.5255	0.4159	0.9342	0.028*
C6	0.62307 (13)	0.28297 (18)	1.00422 (10)	0.0248 (4)
H6	0.6461	0.3587	1.0421	0.030*
C7	0.66115 (13)	0.13804 (18)	1.01328 (9)	0.0227 (3)
C8	0.62657 (13)	0.02820 (18)	0.95705 (10)	0.0239 (3)
H8	0.6521	−0.0712	0.9630	0.029*
C9	0.55519 (12)	0.06344 (18)	0.89265 (10)	0.0229 (3)
H9	0.5323	−0.0122	0.8546	0.027*
N1	0.32818 (11)	0.19058 (16)	0.82922 (9)	0.0249 (3)
H1	0.3303 (16)	0.103 (3)	0.8493 (12)	0.030*
O1	0.73103 (10)	0.09658 (14)	1.07553 (7)	0.0302 (3)
H1A	0.7567 (19)	0.172 (3)	1.0971 (13)	0.036*

	U11	U22	U33	U12	U13	U23
S1	0.0253 (2)	0.0357 (3)	0.0194 (2)	0.00118 (16)	0.00148 (14)	−0.00048 (16)
C1	0.0239 (9)	0.0512 (12)	0.0313 (9)	0.0019 (8)	−0.0045 (7)	−0.0055 (8)
C2	0.0308 (9)	0.0616 (14)	0.0326 (9)	−0.0052 (9)	−0.0028 (8)	−0.0139 (9)
C3	0.0218 (7)	0.0221 (8)	0.0213 (7)	0.0008 (6)	0.0012 (6)	−0.0004 (6)
C4	0.0213 (7)	0.0232 (8)	0.0182 (7)	−0.0019 (6)	0.0023 (6)	0.0005 (6)
C5	0.0265 (8)	0.0188 (7)	0.0252 (8)	−0.0003 (6)	0.0013 (6)	−0.0004 (6)
C6	0.0283 (8)	0.0229 (8)	0.0233 (7)	−0.0042 (6)	−0.0009 (6)	−0.0046 (6)
C7	0.0214 (7)	0.0271 (8)	0.0197 (7)	−0.0034 (6)	0.0012 (6)	0.0013 (6)
C8	0.0259 (8)	0.0204 (7)	0.0254 (8)	0.0011 (6)	0.0009 (6)	−0.0003 (6)
C9	0.0236 (7)	0.0233 (8)	0.0218 (7)	−0.0033 (6)	0.0008 (6)	−0.0027 (6)
N1	0.0219 (7)	0.0266 (7)	0.0262 (7)	0.0003 (5)	0.0013 (5)	0.0001 (6)
O1	0.0337 (7)	0.0275 (6)	0.0293 (6)	−0.0026 (5)	−0.0117 (5)	−0.0012 (5)

S1—C2	1.8049 (19)	C4—C5	1.395 (2)
S1—C3	1.8676 (15)	C5—C6	1.385 (2)
C1—N1	1.463 (2)	C5—H5	0.9500
C1—C2	1.525 (3)	C6—C7	1.390 (2)
C1—H1B	0.9900	C6—H6	0.9500
C1—H1C	0.9900	C7—O1	1.3620 (19)
C2—H2A	0.9900	C7—C8	1.395 (2)
C2—H2B	0.9900	C8—C9	1.385 (2)
C3—N1	1.462 (2)	C8—H8	0.9500
C3—C4	1.507 (2)	C9—H9	0.9500
C3—H3	1.0000	N1—H1	0.85 (2)
C4—C9	1.391 (2)	O1—H1A	0.82 (2)
C2—S1—C3	93.00 (8)	C5—C4—C3	119.73 (14)
N1—C1—C2	109.83 (14)	C6—C5—C4	121.38 (15)
N1—C1—H1B	109.7	C6—C5—H5	119.3
C2—C1—H1B	109.7	C4—C5—H5	119.3
N1—C1—H1C	109.7	C5—C6—C7	119.81 (14)
C2—C1—H1C	109.7	C5—C6—H6	120.1
H1B—C1—H1C	108.2	C7—C6—H6	120.1
C1—C2—S1	105.55 (12)	O1—C7—C6	123.01 (14)
C1—C2—H2A	110.6	O1—C7—C8	117.59 (14)
S1—C2—H2A	110.6	C6—C7—C8	119.40 (14)
C1—C2—H2B	110.6	C9—C8—C7	120.25 (15)
S1—C2—H2B	110.6	C9—C8—H8	119.9
H2A—C2—H2B	108.8	C7—C8—H8	119.9
N1—C3—C4	113.46 (13)	C8—C9—C4	120.91 (14)
N1—C3—S1	106.65 (10)	C8—C9—H9	119.5
C4—C3—S1	112.52 (11)	C4—C9—H9	119.5
N1—C3—H3	108.0	C3—N1—C1	107.78 (13)
C4—C3—H3	108.0	C3—N1—H1	111.2 (14)
S1—C3—H3	108.0	C1—N1—H1	109.8 (13)
C9—C4—C5	118.25 (14)	C7—O1—H1A	108.7 (15)
C9—C4—C3	122.01 (14)
N1—C1—C2—S1	−33.3 (2)	C5—C6—C7—O1	−179.46 (15)
C3—S1—C2—C1	10.32 (15)	C5—C6—C7—C8	0.1 (2)
C2—S1—C3—N1	14.01 (13)	O1—C7—C8—C9	179.74 (14)
C2—S1—C3—C4	139.03 (13)	C6—C7—C8—C9	0.2 (2)
N1—C3—C4—C9	71.65 (19)	C7—C8—C9—C4	−0.2 (2)
S1—C3—C4—C9	−49.55 (18)	C5—C4—C9—C8	0.0 (2)
N1—C3—C4—C5	−107.07 (17)	C3—C4—C9—C8	−178.77 (14)
S1—C3—C4—C5	131.73 (13)	C4—C3—N1—C1	−159.92 (14)
C9—C4—C5—C6	0.3 (2)	S1—C3—N1—C1	−35.47 (15)
C3—C4—C5—C6	179.05 (14)	C2—C1—N1—C3	45.7 (2)
C4—C5—C6—C7	−0.3 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1i	0.85 (2)	2.28 (2)	3.073 (2)	156 (2)
O1—H1A···N1ii	0.82 (2)	1.91 (2)	2.713 (2)	164 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1i	0.85 (2)	2.28 (2)	3.073 (2)	156 (2)
O1—H1A⋯N1ii	0.82 (2)	1.91 (2)	2.713 (2)	164 (2)

Symmetry codes: (i) ; (ii) .