5-(4-Hy-droxy-3-meth-oxy-benz-yl)-1,3-thia-zolidine-2,4-dione monohydrate.

In the title compound, C(11)H(11)NO(4)S·H(2)O, the five-membered thia-zolidine ring is nearly planar, with a maximum deviation of 0.010 (2) Å. The dihedral angle between the thia-zolidine and benzene rings is 49.16 (9)°. Inter-molecular O-H⋯O and N-H⋯O hydrogen bonding is present in the crystal structure.

Related literature

For the therapeutic and pharmacological properties of thia­zolidinediones, see: Day (1999 ▶); Spiegelman (1998 ▶). For the synthesis of the title compound, see: Madhavan et al. (2002 ▶); Shoda et al. (1983 ▶). For related structures, see: Divjaković et al. (1991 ▶); Yathirajan et al. (2005 ▶).

Experimental

Crystal data

C11H11NO4S·H2O

M = 271.28

Monoclinic,

a = 10.684 (4) Å

b = 8.151 (3) Å

c = 14.747 (5) Å

β = 99.657 (4)°

V = 1266.0 (8) Å3

Z = 4

Mo Kα radiation

μ = 0.27 mm−1

T = 293 K

0.15 × 0.12 × 0.10 mm

Data collection

Bruker SMART 1000 CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.960, T max = 0.974

4985 measured reflections

2226 independent reflections

1902 reflections with I > 2σ(I)

R int = 0.047

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.119

S = 1.05

2226 reflections

171 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.22 e Å−3

Δρmin = −0.31 e Å−3

Data collection: SMART (Bruker, 2003 ▶); cell refinement: SAINT (Bruker, 2003 ▶); data reduction: SAINT; 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 I, global. DOI: 10.1107/S1600536810049895/xu5102sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810049895/xu5102Isup2.hkl

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

C11H11NO4S·H2O	F(000) = 568
Mr = 271.28	Dx = 1.423 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 889 reflections
a = 10.684 (4) Å	θ = 2.8–27.5°
b = 8.151 (3) Å	µ = 0.27 mm−1
c = 14.747 (5) Å	T = 293 K
β = 99.657 (4)°	Block, yellow
V = 1266.0 (8) Å3	0.15 × 0.12 × 0.10 mm
Z = 4

Bruker SMART 1000 CCD area-detector diffractometer	2226 independent reflections
Radiation source: fine-focus sealed tube	1902 reflections with I > 2σ(I)
graphite	Rint = 0.047
Detector resolution: 10.0 pixels mm-1	θmax = 25.0°, θmin = 2.2°
φ and ω scans	h = −12→12
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −9→6
Tmin = 0.960, Tmax = 0.974	l = −16→17
4985 measured reflections

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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.119	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ2(Fo2) + (0.0681P)2 + 0.2943P] where P = (Fo2 + 2Fc2)/3
2226 reflections	(Δ/σ)max = 0.001
171 parameters	Δρmax = 0.22 e Å−3
0 restraints	Δρmin = −0.31 e Å−3

Experimental. 1H NMR (300 MHz, CDCl3): δ 8.72(bar, 1H, N—H), 6.87–6.71 (m, 3H, 8-H, 11-H, 12-H), 5.46 (bar, 1H, 10-OH), 4.47–4.51 (m, 1H, 5-H), 3.83 (s, 3H, 9-OCH3), 3.46 (dd, 1H, j=14.4, 4.2, 3-H), 3.06 (dd, 1H, j=14.1, 9.6, 3-H). 13C NMR (300 MHz, CDCl3): δ 174.5, 167.5, 147.8, 145.7, 132.7, 123.1, 116.7, 114.9, 57.2, 56.1, 36.2. MS(ESI) m/z calc. for C11H11NO4S 253.27, found [M–1]+ 252.15. m.p. 109-110°C

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	0.49420 (5)	1.06186 (7)	0.70922 (3)	0.0523 (2)
N3	0.51317 (16)	1.07172 (19)	0.88568 (11)	0.0430 (4)
H3	0.5303	1.1072	0.9413	0.052*
C2	0.5427 (2)	1.1623 (3)	0.81421 (15)	0.0529 (5)
C4	0.45618 (17)	0.9243 (2)	0.86643 (12)	0.0383 (4)
C5	0.43481 (18)	0.8857 (2)	0.76418 (12)	0.0403 (4)
H5	0.4868	0.7902	0.7545	0.048*
C6	0.29661 (18)	0.8453 (3)	0.72695 (13)	0.0448 (5)
H6A	0.2706	0.7526	0.7606	0.054*
H6B	0.2440	0.9383	0.7370	0.054*
C7	0.27553 (18)	0.8048 (2)	0.62553 (13)	0.0407 (4)
C8	0.31489 (17)	0.6537 (2)	0.59516 (12)	0.0386 (4)
H8	0.3523	0.5768	0.6378	0.046*
C9	0.29866 (16)	0.6178 (2)	0.50237 (12)	0.0360 (4)
C10	0.24649 (18)	0.7353 (2)	0.43822 (12)	0.0408 (4)
C11	0.2075 (2)	0.8830 (2)	0.46857 (14)	0.0512 (5)
H11	0.1718	0.9613	0.4261	0.061*
C12	0.2206 (2)	0.9167 (2)	0.56175 (14)	0.0504 (5)
H12	0.1918	1.0163	0.5812	0.061*
C13	0.3765 (2)	0.3430 (3)	0.52648 (16)	0.0541 (5)
H13A	0.3955	0.2494	0.4917	0.081*
H13B	0.3128	0.3141	0.5625	0.081*
H13C	0.4520	0.3781	0.5665	0.081*
O1	0.5944 (2)	1.2929 (2)	0.82373 (12)	0.0877 (7)
O2	0.42480 (14)	0.83322 (17)	0.92352 (9)	0.0483 (4)
O3	0.33054 (14)	0.47280 (16)	0.46520 (9)	0.0485 (4)
O4	0.23570 (15)	0.69314 (17)	0.34819 (9)	0.0537 (4)
H4A	0.2034	0.7691	0.3160	0.080*
O5	0.36833 (18)	0.4211 (2)	0.27286 (12)	0.0558 (4)
H5A	0.336 (4)	0.444 (5)	0.318 (3)	0.134 (16)*
H5B	0.376 (3)	0.518 (4)	0.253 (2)	0.085 (10)*

	U11	U22	U33	U12	U13	U23
S1	0.0699 (4)	0.0527 (4)	0.0342 (3)	−0.0171 (2)	0.0079 (2)	0.0023 (2)
N3	0.0578 (10)	0.0384 (9)	0.0326 (8)	−0.0079 (7)	0.0065 (7)	−0.0046 (6)
C2	0.0715 (14)	0.0423 (11)	0.0453 (11)	−0.0124 (10)	0.0112 (10)	−0.0012 (9)
C4	0.0432 (9)	0.0353 (10)	0.0352 (9)	−0.0008 (7)	0.0033 (7)	−0.0011 (7)
C5	0.0510 (10)	0.0365 (10)	0.0332 (9)	−0.0018 (8)	0.0060 (8)	−0.0021 (8)
C6	0.0518 (11)	0.0454 (11)	0.0374 (10)	−0.0063 (9)	0.0079 (8)	−0.0067 (8)
C7	0.0465 (10)	0.0381 (10)	0.0369 (10)	−0.0074 (8)	0.0050 (8)	−0.0055 (8)
C8	0.0441 (9)	0.0368 (10)	0.0337 (9)	−0.0031 (8)	0.0029 (7)	0.0046 (7)
C9	0.0409 (9)	0.0300 (9)	0.0367 (9)	−0.0029 (7)	0.0051 (7)	−0.0018 (7)
C10	0.0509 (10)	0.0363 (10)	0.0328 (9)	−0.0020 (8)	0.0006 (8)	−0.0018 (7)
C11	0.0727 (14)	0.0357 (10)	0.0405 (10)	0.0059 (10)	−0.0042 (9)	0.0021 (8)
C12	0.0679 (13)	0.0344 (10)	0.0466 (11)	0.0016 (9)	0.0028 (10)	−0.0078 (8)
C13	0.0650 (13)	0.0390 (11)	0.0599 (13)	0.0097 (10)	0.0149 (10)	0.0102 (10)
O1	0.1467 (19)	0.0578 (11)	0.0617 (11)	−0.0545 (12)	0.0262 (11)	−0.0083 (8)
O2	0.0667 (9)	0.0429 (7)	0.0340 (7)	−0.0108 (7)	0.0047 (6)	0.0033 (6)
O3	0.0718 (9)	0.0344 (7)	0.0391 (7)	0.0089 (7)	0.0084 (6)	0.0019 (6)
O4	0.0836 (10)	0.0421 (8)	0.0312 (7)	0.0092 (7)	−0.0022 (7)	−0.0009 (6)
O5	0.0797 (11)	0.0438 (9)	0.0440 (8)	0.0040 (8)	0.0106 (8)	−0.0066 (7)

S1—C2	1.751 (2)	C8—H8	0.9300
S1—C5	1.815 (2)	C9—O3	1.370 (2)
N3—C4	1.356 (2)	C9—C10	1.395 (3)
N3—C2	1.366 (3)	C10—O4	1.358 (2)
N3—H3	0.8600	C10—C11	1.373 (3)
C2—O1	1.197 (3)	C11—C12	1.385 (3)
C4—O2	1.211 (2)	C11—H11	0.9300
C4—C5	1.520 (2)	C12—H12	0.9300
C5—C6	1.523 (3)	C13—O3	1.424 (2)
C5—H5	0.9800	C13—H13A	0.9600
C6—C7	1.511 (3)	C13—H13B	0.9600
C6—H6A	0.9700	C13—H13C	0.9600
C6—H6B	0.9700	O4—H4A	0.8200
C7—C12	1.370 (3)	O5—H5A	0.82 (5)
C7—C8	1.399 (3)	O5—H5B	0.85 (3)
C8—C9	1.382 (3)
C2—S1—C5	92.79 (9)	C9—C8—C7	120.60 (17)
C4—N3—C2	118.11 (16)	C9—C8—H8	119.7
C4—N3—H3	120.9	C7—C8—H8	119.7
C2—N3—H3	120.9	O3—C9—C8	125.52 (16)
O1—C2—N3	123.5 (2)	O3—C9—C10	114.77 (15)
O1—C2—S1	125.58 (18)	C8—C9—C10	119.71 (17)
N3—C2—S1	110.93 (15)	O4—C10—C11	124.07 (17)
O2—C4—N3	124.38 (17)	O4—C10—C9	116.61 (16)
O2—C4—C5	123.37 (17)	C11—C10—C9	119.31 (17)
N3—C4—C5	112.25 (16)	C10—C11—C12	120.76 (18)
C4—C5—C6	112.19 (15)	C10—C11—H11	119.6
C4—C5—S1	105.90 (13)	C12—C11—H11	119.6
C6—C5—S1	113.61 (13)	C7—C12—C11	120.64 (19)
C4—C5—H5	108.3	C7—C12—H12	119.7
C6—C5—H5	108.3	C11—C12—H12	119.7
S1—C5—H5	108.3	O3—C13—H13A	109.5
C7—C6—C5	112.25 (15)	O3—C13—H13B	109.5
C7—C6—H6A	109.2	H13A—C13—H13B	109.5
C5—C6—H6A	109.2	O3—C13—H13C	109.5
C7—C6—H6B	109.2	H13A—C13—H13C	109.5
C5—C6—H6B	109.2	H13B—C13—H13C	109.5
H6A—C6—H6B	107.9	C9—O3—C13	118.00 (15)
C12—C7—C8	118.92 (18)	C10—O4—H4A	109.5
C12—C7—C6	120.66 (18)	H5A—O5—H5B	98 (3)
C8—C7—C6	120.40 (17)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3···O2i	0.86	2.03	2.886 (2)	174.
O4—H4A···O5ii	0.82	1.87	2.685 (2)	171.
O5—H5A···O3	0.82 (5)	2.19 (5)	2.962 (2)	156 (4)
O5—H5A···O4	0.82 (5)	2.37 (4)	2.947 (2)	127 (4)
O5—H5B···O1iii	0.85 (3)	1.97 (3)	2.795 (3)	163 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3⋯O2i	0.86	2.03	2.886 (2)	174
O4—H4A⋯O5ii	0.82	1.87	2.685 (2)	171
O5—H5A⋯O3	0.82 (5)	2.19 (5)	2.962 (2)	156 (4)
O5—H5A⋯O4	0.82 (5)	2.37 (4)	2.947 (2)	127 (4)
O5—H5B⋯O1iii	0.85 (3)	1.97 (3)	2.795 (3)	163 (3)

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