(5E)-5-(4-Hydr-oxy-3-methoxy-benzyl-idene)-2-thioxo-1,3-thia-zolidin-4-one methanol monosolvate.

In the title compound, C(11)H(9)NO(3)S(2)·CH(4)O, the dihedral angle between the aromatic rings is 3.57 (16)° and intra-molecular O-H⋯O and C-H⋯S inter-actions occur. In the crystal, the thia-zolidin-4-one mol-ecules are linked by N-H⋯O hydrogen bonds, forming chains. The hydrogen-bond motifs lead to S(5), S(6) and R(3) (3)(8) ring motifs. There exist C=O⋯π inter-actions between the heterocyclic rings and π-π inter-actions between the heterocyclic and benzene rings at distances of 3.455 (2) and 3.602 (2) Å, respectively. The methanol solvent mol-ecule is disordered over two sets of sites in a 0.542 (9):0.458 (9) ratio.

Related literature

For related structures, see: Barreiro et al. (2007 ▶); Shahwar et al. (2009 ▶). For graph-set notation, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C11H9NO3S2·CH4O

M = 299.35

Orthorhombic,

a = 17.731 (2) Å

b = 11.7528 (14) Å

c = 6.5715 (6) Å

V = 1369.4 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.40 mm−1

T = 296 K

0.26 × 0.13 × 0.12 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2007 ▶) T min = 0.942, T max = 0.955

7574 measured reflections

2472 independent reflections

1807 reflections with I > 2σ(I)

R int = 0.045

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.070

S = 1.02

2472 reflections

185 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.17 e Å−3

Δρmin = −0.21 e Å−3

Absolute structure: Flack (1983 ▶), 829 Friedal Pairs

Flack parameter: 0.01 (8)

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); 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 (Farrugia, 1997 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809039567/hb5118sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809039567/hb5118Isup2.hkl

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

C11H9NO3S2·CH4O	F(000) = 624
Mr = 299.35	Dx = 1.452 Mg m−3
Orthorhombic, Pna21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 2472 reflections
a = 17.731 (2) Å	θ = 2.9–27.1°
b = 11.7528 (14) Å	µ = 0.40 mm−1
c = 6.5715 (6) Å	T = 296 K
V = 1369.4 (3) Å3	Cut needle, dark brown
Z = 4	0.26 × 0.13 × 0.12 mm

Bruker Kappa APEXII CCD diffractometer	2472 independent reflections
Radiation source: fine-focus sealed tube	1807 reflections with I > 2σ(I)
graphite	Rint = 0.045
Detector resolution: 7.50 pixels mm-1	θmax = 27.1°, θmin = 2.9°
ω scans	h = −22→22
Absorption correction: multi-scan (SADABS; Bruker, 2007)	k = −13→15
Tmin = 0.942, Tmax = 0.955	l = −5→8
7574 measured reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.039	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.070	w = 1/[σ2(Fo2) + (0.0145P)2 + 0.2762P] where P = (Fo2 + 2Fc2)/3
S = 1.02	(Δ/σ)max < 0.001
2472 reflections	Δρmax = 0.17 e Å−3
185 parameters	Δρmin = −0.21 e Å−3
1 restraint	Absolute structure: Flack (1983), 829 Friedal Pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.01 (8)

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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	Occ. (<1)
S1	0.36194 (4)	0.02090 (7)	0.57918 (14)	0.0440 (3)
S2	0.41466 (5)	−0.10304 (9)	0.20833 (15)	0.0609 (4)
O1	0.30380 (12)	0.3234 (2)	1.4811 (3)	0.0514 (9)
O2	0.41511 (11)	0.2575 (2)	1.2416 (3)	0.0540 (9)
O3	0.15476 (12)	−0.0232 (2)	0.4387 (3)	0.0531 (9)
N1	0.27209 (14)	−0.0654 (2)	0.3174 (4)	0.0403 (9)
C1	0.25139 (18)	0.1479 (3)	0.9536 (4)	0.0352 (10)
C2	0.32661 (18)	0.1714 (3)	1.0013 (5)	0.0383 (11)
C3	0.34462 (16)	0.2296 (3)	1.1767 (5)	0.0377 (11)
C4	0.28684 (17)	0.2662 (3)	1.3082 (4)	0.0373 (11)
C5	0.21274 (17)	0.2455 (3)	1.2609 (5)	0.0412 (11)
C6	0.19503 (16)	0.1858 (3)	1.0864 (5)	0.0411 (11)
C7	0.22722 (18)	0.0873 (3)	0.7745 (5)	0.0410 (11)
C8	0.26494 (16)	0.0363 (3)	0.6206 (4)	0.0376 (11)
C9	0.22317 (17)	−0.0188 (3)	0.4558 (5)	0.0405 (11)
C10	0.34766 (17)	−0.0547 (3)	0.3526 (5)	0.0392 (11)
C11	0.47733 (18)	0.2154 (4)	1.1321 (6)	0.0780 (18)
O4A	0.4252 (3)	0.4356 (7)	0.5888 (10)	0.078 (3)	0.542 (9)
C12A	0.5055 (2)	0.4123 (5)	0.6066 (13)	0.096 (2)	0.542 (9)
O4B	0.4343 (2)	0.3568 (4)	0.6677 (9)	0.059 (3)	0.458 (9)
C12B	0.4913 (2)	0.4044 (4)	0.6141 (9)	0.096 (2)	0.458 (9)
H1	0.3525 (17)	0.334 (3)	1.499 (5)	0.0617*
H1N	0.25564	−0.10029	0.21132	0.0483*
H2	0.36478	0.14769	0.91393	0.0460*
H5	0.17457	0.27152	1.34604	0.0495*
H6	0.14477	0.17047	1.05653	0.0492*
H7	0.17507	0.08219	0.76231	0.0494*
H11A	0.47613	0.13375	1.13217	0.1166*
H11B	0.52316	0.24114	1.19480	0.1166*
H11C	0.47516	0.24266	0.99447	0.1166*
H4A	0.401 (4)	0.449 (6)	0.717 (13)	0.0935*	0.542 (9)
H12C	0.51734	0.39385	0.74524	0.1441*	0.542 (9)
H12A	0.53358	0.47831	0.56588	0.1441*	0.542 (9)
H12B	0.51849	0.34937	0.52036	0.1441*	0.542 (9)
H4B	0.40848	0.40061	0.73547	0.0709*	0.458 (9)
H12D	0.50918	0.45230	0.72210	0.1441*	0.458 (9)
H12E	0.48086	0.44993	0.49615	0.1441*	0.458 (9)
H12F	0.52902	0.34877	0.58154	0.1441*	0.458 (9)

	U11	U22	U33	U12	U13	U23
S1	0.0445 (4)	0.0523 (5)	0.0353 (4)	0.0038 (4)	−0.0056 (4)	−0.0094 (5)
S2	0.0552 (5)	0.0804 (8)	0.0472 (5)	0.0164 (5)	0.0008 (5)	−0.0137 (6)
O1	0.0444 (14)	0.0726 (19)	0.0372 (13)	0.0026 (13)	0.0019 (11)	−0.0231 (12)
O2	0.0383 (13)	0.0796 (17)	0.0442 (14)	−0.0046 (12)	0.0060 (11)	−0.0230 (13)
O3	0.0435 (13)	0.0691 (18)	0.0467 (14)	0.0004 (12)	−0.0084 (11)	−0.0146 (13)
N1	0.0527 (17)	0.0388 (18)	0.0293 (14)	0.0048 (14)	−0.0049 (12)	−0.0101 (13)
C1	0.0417 (17)	0.0343 (19)	0.0295 (17)	0.0022 (14)	0.0031 (14)	−0.0013 (14)
C2	0.0442 (19)	0.041 (2)	0.0297 (17)	0.0029 (16)	0.0060 (14)	−0.0062 (16)
C3	0.0389 (17)	0.040 (2)	0.0341 (19)	0.0002 (15)	0.0035 (15)	−0.0030 (17)
C4	0.047 (2)	0.037 (2)	0.0278 (18)	0.0023 (15)	0.0007 (15)	−0.0093 (16)
C5	0.0414 (19)	0.051 (2)	0.0313 (18)	0.0070 (17)	0.0024 (15)	−0.0069 (16)
C6	0.0372 (17)	0.045 (2)	0.0410 (18)	0.0037 (14)	−0.0008 (18)	−0.001 (2)
C7	0.0437 (18)	0.041 (2)	0.0383 (19)	0.0002 (16)	−0.0016 (15)	0.0005 (17)
C8	0.0464 (17)	0.039 (2)	0.0275 (19)	0.0024 (14)	−0.0081 (14)	−0.0034 (15)
C9	0.048 (2)	0.037 (2)	0.0364 (18)	0.0040 (17)	−0.0041 (16)	−0.0005 (16)
C10	0.047 (2)	0.038 (2)	0.0327 (18)	0.0049 (15)	−0.0088 (15)	−0.0018 (15)
C11	0.044 (2)	0.113 (4)	0.077 (3)	−0.005 (2)	0.0177 (18)	−0.026 (3)
O4A	0.048 (3)	0.119 (6)	0.067 (4)	0.004 (3)	0.005 (3)	−0.039 (5)
C12A	0.064 (3)	0.131 (5)	0.093 (4)	−0.008 (3)	0.011 (3)	−0.019 (4)
O4B	0.043 (3)	0.079 (6)	0.055 (4)	−0.001 (3)	0.006 (3)	−0.020 (4)
C12B	0.064 (3)	0.131 (5)	0.093 (4)	−0.008 (3)	0.011 (3)	−0.019 (4)

S1—C8	1.751 (3)	C3—C4	1.408 (4)
S1—C10	1.752 (3)	C4—C5	1.372 (4)
S2—C10	1.623 (3)	C5—C6	1.381 (5)
O1—C4	1.354 (4)	C7—C8	1.353 (4)
O2—C3	1.361 (4)	C8—C9	1.463 (4)
O2—C11	1.407 (4)	C2—H2	0.9300
O3—C9	1.219 (4)	C5—H5	0.9300
O1—H1	0.88 (3)	C6—H6	0.9300
O4A—C12A	1.455 (7)	C7—H7	0.9300
O4B—C12B	1.208 (6)	C11—H11A	0.9600
O4A—H4A	0.96 (8)	C11—H11B	0.9600
O4B—H4B	0.8200	C11—H11C	0.9600
N1—C10	1.366 (4)	C12A—H12B	0.9600
N1—C9	1.371 (4)	C12A—H12C	0.9600
N1—H1N	0.8600	C12A—H12A	0.9600
C1—C2	1.398 (5)	C12B—H12D	0.9600
C1—C7	1.441 (4)	C12B—H12E	0.9600
C1—C6	1.400 (4)	C12B—H12F	0.9600
C2—C3	1.378 (5)
C8—S1—C10	92.44 (14)	S2—C10—N1	126.0 (3)
C3—O2—C11	118.4 (3)	S1—C10—S2	124.63 (19)
C4—O1—H1	114 (2)	C3—C2—H2	120.00
C12A—O4A—H4A	114 (4)	C1—C2—H2	120.00
C12B—O4B—H4B	110.00	C4—C5—H5	120.00
C9—N1—C10	118.1 (3)	C6—C5—H5	120.00
C10—N1—H1N	121.00	C5—C6—H6	119.00
C9—N1—H1N	121.00	C1—C6—H6	119.00
C2—C1—C7	124.4 (3)	C8—C7—H7	113.00
C2—C1—C6	118.6 (3)	C1—C7—H7	113.00
C6—C1—C7	117.0 (3)	O2—C11—H11C	109.00
C1—C2—C3	120.5 (3)	O2—C11—H11A	110.00
O2—C3—C4	113.7 (3)	O2—C11—H11B	109.00
O2—C3—C2	126.5 (3)	H11B—C11—H11C	109.00
C2—C3—C4	119.8 (3)	H11A—C11—H11B	109.00
O1—C4—C5	119.4 (3)	H11A—C11—H11C	109.00
C3—C4—C5	120.3 (3)	O4A—C12A—H12B	109.00
O1—C4—C3	120.4 (3)	O4A—C12A—H12C	109.00
C4—C5—C6	119.8 (3)	O4A—C12A—H12A	109.00
C1—C6—C5	121.2 (3)	H12A—C12A—H12C	109.00
C1—C7—C8	133.1 (3)	H12B—C12A—H12C	110.00
S1—C8—C9	109.7 (2)	H12A—C12A—H12B	109.00
S1—C8—C7	130.4 (2)	O4B—C12B—H12D	109.00
C7—C8—C9	120.0 (3)	O4B—C12B—H12E	109.00
O3—C9—C8	126.2 (3)	O4B—C12B—H12F	109.00
N1—C9—C8	110.3 (3)	H12D—C12B—H12E	110.00
O3—C9—N1	123.5 (3)	H12D—C12B—H12F	110.00
S1—C10—N1	109.4 (2)	H12E—C12B—H12F	110.00
C10—S1—C8—C7	179.4 (4)	C1—C2—C3—O2	179.7 (3)
C10—S1—C8—C9	0.3 (3)	C1—C2—C3—C4	−0.4 (5)
C8—S1—C10—S2	179.6 (3)	O2—C3—C4—O1	−0.1 (5)
C8—S1—C10—N1	−0.1 (3)	O2—C3—C4—C5	179.1 (3)
C11—O2—C3—C2	−6.2 (5)	C2—C3—C4—O1	180.0 (3)
C11—O2—C3—C4	173.9 (3)	C2—C3—C4—C5	−0.9 (5)
C10—N1—C9—O3	179.8 (3)	O1—C4—C5—C6	−179.1 (3)
C10—N1—C9—C8	0.4 (4)	C3—C4—C5—C6	1.8 (5)
C9—N1—C10—S1	−0.2 (4)	C4—C5—C6—C1	−1.4 (5)
C9—N1—C10—S2	−179.8 (3)	C1—C7—C8—S1	1.4 (6)
C6—C1—C2—C3	0.7 (5)	C1—C7—C8—C9	−179.5 (4)
C7—C1—C2—C3	−179.7 (3)	S1—C8—C9—O3	−179.8 (3)
C2—C1—C6—C5	0.2 (5)	S1—C8—C9—N1	−0.4 (3)
C7—C1—C6—C5	−179.4 (3)	C7—C8—C9—O3	1.0 (5)
C2—C1—C7—C8	3.1 (6)	C7—C8—C9—N1	−179.6 (3)
C6—C1—C7—C8	−177.4 (4)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2	0.88 (3)	2.21 (3)	2.641 (3)	109 (3)
C2—H2···S1	0.93	2.66	3.349 (3)	132
O1—H1···O4Ai	0.88 (3)	1.85 (3)	2.622 (7)	145 (3)
N1—H1N···O1ii	0.86	2.05	2.899 (3)	169
O4A—H4A···O3iii	0.96 (8)	1.79 (8)	2.744 (7)	173 (7)
C12A—H12A···O3iv	0.96	2.37	3.150 (5)	139

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O2	0.88 (3)	2.21 (3)	2.641 (3)	109 (3)
C2—H2⋯S1	0.93	2.66	3.349 (3)	132
O1—H1⋯O4Ai	0.88 (3)	1.85 (3)	2.622 (7)	145 (3)
N1—H1N⋯O1ii	0.86	2.05	2.899 (3)	169
O4A—H4A⋯O3iii	0.96 (8)	1.79 (8)	2.744 (7)	173 (7)
C12A—H12A⋯O3iv	0.96	2.37	3.150 (5)	139

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) . Cg2 is the centroid of the C1–C6 benzene ring.