(5Z)-5-(2-Hydroxy-benzyl-idene)-2-thioxo-1,3-thia-zolidin-4-one methanol hemisolvate.

In the title compound, C(10)H(7)NO(2)S(2)·0.5CH(3)OH, the dihedral angle between the aromatic rings is 11.43 (11)° and a short intra-molecular C-H⋯S contact occurs. The methanol solvent mol-ecule is equally disordered over two sets of sites. In the crystal, inversion dimers linked by pairs of N-H⋯O hydrogen bonds occur. The methanol solvent mol-ecule connects the dimers through O-H⋯S and O-H⋯O inter-molecular hydrogen bonds. Further stability is afforded by C-H⋯π and π-π inter-actions [centroid-centroid separation = 3.5948 (13) Å].

Related literature

For related structures, see: Barreiro et al. (2007 ▶); Delgado et al. (2006 ▶). For graph-set notation, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C10H7NO2S2·0.5CH4O

M = 253.33

Monoclinic,

a = 20.4859 (16) Å

b = 6.4422 (4) Å

c = 18.4377 (15) Å

β = 108.724 (4)°

V = 2304.5 (3) Å3

Z = 8

Mo Kα radiation

μ = 0.45 mm−1

T = 296 K

0.28 × 0.15 × 0.12 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.925, T max = 0.947

11803 measured reflections

2636 independent reflections

1562 reflections with I > 2σ(I)

R int = 0.040

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.101

S = 1.03

2636 reflections

167 parameters

8 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.30 e Å−3

Δρmin = −0.28 e Å−3

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/S1600536809039555/hb5115sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809039555/hb5115Isup2.hkl

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

C10H7NO2S2·0.5CH4O	F(000) = 1048
Mr = 253.33	Dx = 1.460 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 2636 reflections
a = 20.4859 (16) Å	θ = 2.1–27.5°
b = 6.4422 (4) Å	µ = 0.45 mm−1
c = 18.4377 (15) Å	T = 296 K
β = 108.724 (4)°	Cut needle, light red
V = 2304.5 (3) Å3	0.28 × 0.15 × 0.12 mm
Z = 8

Bruker Kappa APEXII CCD diffractometer	2636 independent reflections
Radiation source: fine-focus sealed tube	1562 reflections with I > 2σ(I)
graphite	Rint = 0.040
Detector resolution: 7.50 pixels mm-1	θmax = 27.5°, θmin = 2.1°
ω scans	h = −22→26
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −5→8
Tmin = 0.925, Tmax = 0.947	l = −23→22
11803 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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.101	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ2(Fo2) + (0.0357P)2 + 1.2743P] where P = (Fo2 + 2Fc2)/3
2636 reflections	(Δ/σ)max < 0.001
167 parameters	Δρmax = 0.30 e Å−3
8 restraints	Δρmin = −0.28 e Å−3

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	0.15938 (4)	0.58242 (10)	−0.00444 (4)	0.0600 (2)
S2	0.14589 (4)	0.94002 (13)	−0.11023 (5)	0.0802 (3)
O1	0.06021 (9)	0.1385 (3)	0.18770 (11)	0.0619 (7)
O2	0.01091 (8)	0.7729 (2)	0.06117 (9)	0.0516 (6)
N1	0.06936 (9)	0.8655 (3)	−0.02055 (10)	0.0467 (7)
C1	0.14189 (11)	0.2372 (3)	0.12922 (12)	0.0389 (7)
C2	0.12016 (12)	0.0955 (3)	0.17442 (12)	0.0428 (8)
C3	0.15870 (12)	−0.0790 (4)	0.20299 (13)	0.0485 (8)
C4	0.21827 (13)	−0.1171 (4)	0.18715 (13)	0.0531 (9)
C5	0.24140 (13)	0.0198 (4)	0.14359 (14)	0.0566 (9)
C6	0.20350 (13)	0.1944 (4)	0.11522 (13)	0.0512 (9)
C7	0.10043 (11)	0.4192 (3)	0.10120 (12)	0.0422 (8)
C8	0.10408 (11)	0.5631 (3)	0.05020 (12)	0.0396 (7)
C9	0.05620 (11)	0.7391 (3)	0.03308 (12)	0.0405 (8)
C10	0.12115 (12)	0.8120 (4)	−0.04789 (13)	0.0502 (8)
O11	−0.0100 (5)	0.8280 (6)	0.2318 (3)	0.066 (3)	0.500
C11	0.014 (2)	0.6235 (11)	0.262 (3)	0.112 (14)	0.500
H1N	0.04538	0.97578	−0.03643	0.0561*
H1O	0.04906	0.03909	0.20888	0.0743*
H3	0.14403	−0.17151	0.23327	0.0582*
H4	0.24344	−0.23670	0.20598	0.0637*
H5	0.28232	−0.00571	0.13348	0.0680*
H6	0.21932	0.28673	0.08585	0.0614*
H7	0.06521	0.44009	0.12207	0.0507*
H11	−0.035 (3)	0.804 (7)	0.1868 (16)	0.0792*	0.500
H11A	−0.012 (4)	0.500 (7)	0.244 (5)	0.1677*	0.500
H11B	0.019 (4)	0.608 (13)	0.316 (4)	0.1677*	0.500
H11C	0.058 (3)	0.572 (11)	0.265 (5)	0.1677*	0.500

	U11	U22	U33	U12	U13	U23
S1	0.0676 (4)	0.0634 (4)	0.0594 (4)	0.0280 (4)	0.0349 (4)	0.0186 (3)
S2	0.0750 (5)	0.0963 (6)	0.0837 (6)	0.0304 (4)	0.0457 (4)	0.0451 (5)
O1	0.0609 (11)	0.0550 (11)	0.0805 (13)	0.0130 (9)	0.0376 (10)	0.0213 (9)
O2	0.0495 (10)	0.0516 (10)	0.0591 (11)	0.0152 (8)	0.0249 (9)	0.0124 (8)
N1	0.0446 (12)	0.0464 (11)	0.0511 (12)	0.0133 (9)	0.0180 (10)	0.0116 (10)
C1	0.0446 (13)	0.0359 (12)	0.0364 (13)	0.0055 (10)	0.0131 (10)	−0.0019 (10)
C2	0.0448 (13)	0.0401 (13)	0.0433 (13)	0.0031 (11)	0.0137 (11)	−0.0050 (11)
C3	0.0596 (16)	0.0406 (13)	0.0448 (14)	0.0038 (12)	0.0162 (12)	0.0050 (11)
C4	0.0631 (17)	0.0431 (14)	0.0490 (15)	0.0180 (12)	0.0124 (13)	0.0002 (12)
C5	0.0598 (16)	0.0600 (16)	0.0560 (16)	0.0212 (13)	0.0269 (13)	0.0061 (13)
C6	0.0589 (16)	0.0516 (15)	0.0481 (15)	0.0113 (13)	0.0243 (12)	0.0067 (12)
C7	0.0425 (13)	0.0409 (13)	0.0439 (13)	0.0037 (10)	0.0148 (11)	−0.0049 (11)
C8	0.0422 (13)	0.0374 (12)	0.0387 (12)	0.0049 (10)	0.0123 (10)	−0.0002 (11)
C9	0.0385 (13)	0.0410 (13)	0.0394 (13)	0.0029 (11)	0.0087 (11)	−0.0007 (11)
C10	0.0483 (14)	0.0550 (15)	0.0468 (15)	0.0131 (12)	0.0146 (12)	0.0081 (12)
O11	0.082 (7)	0.067 (2)	0.049 (5)	−0.007 (2)	0.022 (5)	−0.0010 (19)
C11	0.16 (3)	0.063 (3)	0.15 (3)	−0.004 (7)	0.10 (2)	0.002 (8)

S1—C8	1.745 (2)	C2—C3	1.378 (3)
S1—C10	1.744 (3)	C3—C4	1.365 (4)
S2—C10	1.622 (3)	C4—C5	1.375 (4)
O1—C2	1.356 (3)	C5—C6	1.372 (4)
O2—C9	1.219 (3)	C7—C8	1.340 (3)
O1—H1O	0.8200	C8—C9	1.466 (3)
O11—C11	1.45 (2)	C3—H3	0.9300
O11—H11	0.84 (3)	C4—H4	0.9300
N1—C9	1.373 (3)	C5—H5	0.9300
N1—C10	1.357 (3)	C6—H6	0.9300
N1—H1N	0.8600	C7—H7	0.9300
C1—C7	1.443 (3)	C11—H11A	0.96 (6)
C1—C2	1.402 (3)	C11—H11B	0.97 (9)
C1—C6	1.395 (4)	C11—H11C	0.95 (8)
C8—S1—C10	92.67 (11)	O2—C9—C8	126.50 (19)
C2—O1—H1O	109.00	O2—C9—N1	123.54 (19)
C11—O11—H11	104 (4)	S1—C10—S2	124.08 (16)
C9—N1—C10	118.3 (2)	S2—C10—N1	126.4 (2)
C10—N1—H1N	121.00	S1—C10—N1	109.52 (17)
C9—N1—H1N	121.00	C4—C3—H3	120.00
C2—C1—C7	118.7 (2)	C2—C3—H3	120.00
C2—C1—C6	117.4 (2)	C3—C4—H4	120.00
C6—C1—C7	123.9 (2)	C5—C4—H4	120.00
O1—C2—C3	122.6 (2)	C6—C5—H5	120.00
O1—C2—C1	116.96 (19)	C4—C5—H5	120.00
C1—C2—C3	120.4 (2)	C1—C6—H6	119.00
C2—C3—C4	120.5 (2)	C5—C6—H6	119.00
C3—C4—C5	120.6 (2)	C1—C7—H7	115.00
C4—C5—C6	119.3 (3)	C8—C7—H7	115.00
C1—C6—C5	121.8 (2)	O11—C11—H11A	123 (6)
C1—C7—C8	130.9 (2)	O11—C11—H11B	113 (6)
S1—C8—C9	109.51 (15)	O11—C11—H11C	123 (6)
C7—C8—C9	120.2 (2)	H11A—C11—H11B	98 (8)
S1—C8—C7	130.34 (18)	H11A—C11—H11C	98 (7)
N1—C9—C8	109.96 (19)	H11B—C11—H11C	97 (8)
C10—S1—C8—C7	179.8 (2)	C2—C1—C7—C8	−170.5 (2)
C10—S1—C8—C9	0.0 (2)	C6—C1—C7—C8	10.7 (4)
C8—S1—C10—S2	179.12 (17)	O1—C2—C3—C4	179.1 (2)
C8—S1—C10—N1	0.05 (18)	C1—C2—C3—C4	−0.5 (3)
C10—N1—C9—O2	−179.9 (2)	C2—C3—C4—C5	1.2 (4)
C10—N1—C9—C8	0.1 (3)	C3—C4—C5—C6	−0.8 (4)
C9—N1—C10—S1	−0.1 (3)	C4—C5—C6—C1	−0.1 (4)
C9—N1—C10—S2	−179.14 (18)	C1—C7—C8—S1	2.0 (4)
C6—C1—C2—O1	180.0 (2)	C1—C7—C8—C9	−178.2 (2)
C6—C1—C2—C3	−0.4 (3)	S1—C8—C9—O2	179.96 (19)
C7—C1—C2—O1	1.1 (3)	S1—C8—C9—N1	−0.1 (2)
C7—C1—C2—C3	−179.3 (2)	C7—C8—C9—O2	0.1 (3)
C2—C1—C6—C5	0.7 (3)	C7—C8—C9—N1	−179.90 (19)
C7—C1—C6—C5	179.5 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O2i	0.86	1.95	2.811 (2)	173
O1—H1O···O11ii	0.82	1.95	2.735 (7)	159
O1—H1O···O11iii	0.82	2.06	2.871 (7)	169
O11—H11···S2i	0.84 (3)	2.80 (5)	3.317 (8)	122 (4)
C6—H6···S1	0.93	2.57	3.264 (3)	132
C4—H4···Cg2iv	0.93	2.81	3.599 (3)	143

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O2i	0.86	1.95	2.811 (2)	173
O1—H1O⋯O11ii	0.82	1.95	2.735 (7)	159
O1—H1O⋯O11iii	0.82	2.06	2.871 (7)	169
O11—H11⋯S2i	0.84 (3)	2.80 (5)	3.317 (8)	122 (4)
C6—H6⋯S1	0.93	2.57	3.264 (3)	132
C4—H4⋯Cg2iv	0.93	2.81	3.599 (3)	143

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