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

In the title compound, C(16)H(11)NO(2)S(2), the dihedral angles between the heterocyclic ring and the phenyl and anilinic benzene rings are 9.68 (13) and 79.26 (6)°, respectively, and an intra-molecular C-H⋯S inter-action occurs. In the crystal, inversion dimers linked by pairs of O-H⋯O hydrogen bonds occur, leading to R(2) (2)(10) loops, and C-H⋯O and weak C-H⋯π inter-actions further consolidate the packing.

Related literature

For related structures, see: Linden et al. (1999 ▶); Shahwar et al. (2009a ▶, 2009b ▶). For graph-set theory, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C16H11NO2S2

M = 313.40

Monoclinic,

a = 11.6553 (7) Å

b = 7.3424 (4) Å

c = 16.8256 (10) Å

β = 95.131 (2)°

V = 1434.13 (14) Å3

Z = 4

Mo Kα radiation

μ = 0.37 mm−1

T = 296 K

0.26 × 0.18 × 0.17 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.924, T max = 0.937

15580 measured reflections

3481 independent reflections

2194 reflections with I > 2σ(I)

R int = 0.048

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.102

S = 1.01

3481 reflections

191 parameters

H-atom parameters constrained

Δρmax = 0.26 e Å−3

Δρmin = −0.27 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/S1600536809044286/hb5180sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809044286/hb5180Isup2.hkl

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

C16H11NO2S2	F(000) = 648
Mr = 313.40	Dx = 1.452 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 3481 reflections
a = 11.6553 (7) Å	θ = 2.0–28.0°
b = 7.3424 (4) Å	µ = 0.37 mm−1
c = 16.8256 (10) Å	T = 296 K
β = 95.131 (2)°	Prisms, orange yellow
V = 1434.13 (14) Å3	0.26 × 0.18 × 0.17 mm
Z = 4

Bruker Kappa APEXII CCD diffractometer	3481 independent reflections
Radiation source: fine-focus sealed tube	2194 reflections with I > 2σ(I)
graphite	Rint = 0.048
Detector resolution: 7.40 pixels mm-1	θmax = 28.0°, θmin = 2.0°
ω scans	h = −15→14
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −9→9
Tmin = 0.924, Tmax = 0.937	l = −22→22
15580 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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.102	H-atom parameters constrained
S = 1.01	w = 1/[σ2(Fo2) + (0.0375P)2 + 0.326P] where P = (Fo2 + 2Fc2)/3
3481 reflections	(Δ/σ)max < 0.001
191 parameters	Δρmax = 0.26 e Å−3
0 restraints	Δρmin = −0.27 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
S1	0.16936 (5)	0.50419 (7)	0.48587 (3)	0.0463 (2)
S2	0.12725 (6)	0.16709 (8)	0.57270 (4)	0.0591 (2)
O1	0.45774 (15)	0.5967 (2)	0.60654 (9)	0.0572 (6)
O2	0.40155 (14)	1.1358 (2)	0.44795 (9)	0.0515 (6)
N1	0.30920 (15)	0.3922 (2)	0.60195 (9)	0.0376 (6)
C1	0.35642 (18)	0.2866 (3)	0.66982 (12)	0.0370 (7)
C2	0.3410 (2)	0.3461 (3)	0.74551 (12)	0.0432 (7)
C3	0.3835 (2)	0.2416 (3)	0.81002 (12)	0.0477 (8)
C4	0.4398 (2)	0.0815 (3)	0.79786 (14)	0.0497 (8)
C5	0.4550 (2)	0.0235 (3)	0.72188 (14)	0.0524 (9)
C6	0.4139 (2)	0.1273 (3)	0.65678 (13)	0.0466 (8)
C7	0.20684 (19)	0.3439 (3)	0.55947 (12)	0.0399 (7)
C8	0.29274 (19)	0.6347 (3)	0.51013 (11)	0.0385 (7)
C9	0.3643 (2)	0.5470 (3)	0.57636 (12)	0.0401 (7)
C10	0.32304 (19)	0.7938 (3)	0.47846 (12)	0.0418 (7)
C11	0.26629 (19)	0.9014 (3)	0.41462 (11)	0.0379 (7)
C12	0.31041 (19)	1.0743 (3)	0.39934 (12)	0.0389 (7)
C13	0.2611 (2)	1.1796 (3)	0.33719 (13)	0.0494 (8)
C14	0.1673 (2)	1.1153 (3)	0.28976 (13)	0.0540 (9)
C15	0.1207 (2)	0.9486 (3)	0.30463 (13)	0.0533 (9)
C16	0.1702 (2)	0.8438 (3)	0.36550 (13)	0.0478 (8)
H2	0.30268	0.45483	0.75331	0.0518*
H2A	0.43058	1.22336	0.42710	0.0772*
H3	0.37382	0.28003	0.86166	0.0572*
H4	0.46807	0.01166	0.84139	0.0596*
H5	0.49284	−0.08572	0.71418	0.0629*
H6	0.42501	0.08995	0.60520	0.0559*
H10	0.39181	0.84263	0.50141	0.0502*
H13	0.29121	1.29390	0.32743	0.0593*
H14	0.13538	1.18544	0.24737	0.0648*
H15	0.05592	0.90715	0.27356	0.0640*
H16	0.13881	0.72999	0.37452	0.0574*

	U11	U22	U33	U12	U13	U23
S1	0.0458 (4)	0.0443 (3)	0.0466 (3)	−0.0085 (3)	−0.0083 (2)	0.0067 (2)
S2	0.0556 (4)	0.0454 (3)	0.0756 (4)	−0.0154 (3)	0.0014 (3)	0.0099 (3)
O1	0.0538 (11)	0.0551 (10)	0.0582 (10)	−0.0197 (8)	−0.0194 (8)	0.0209 (8)
O2	0.0534 (11)	0.0476 (9)	0.0518 (9)	−0.0149 (8)	−0.0042 (8)	0.0148 (7)
N1	0.0414 (11)	0.0340 (9)	0.0369 (9)	−0.0023 (8)	0.0001 (8)	0.0047 (7)
C1	0.0387 (13)	0.0322 (10)	0.0397 (11)	−0.0023 (9)	0.0020 (9)	0.0042 (8)
C2	0.0475 (14)	0.0371 (11)	0.0449 (12)	0.0020 (10)	0.0036 (10)	0.0007 (9)
C3	0.0533 (16)	0.0514 (13)	0.0380 (12)	−0.0027 (12)	0.0027 (10)	0.0026 (10)
C4	0.0480 (15)	0.0486 (13)	0.0514 (14)	−0.0004 (11)	−0.0012 (11)	0.0169 (11)
C5	0.0556 (17)	0.0388 (12)	0.0631 (15)	0.0100 (11)	0.0071 (12)	0.0076 (10)
C6	0.0573 (16)	0.0412 (12)	0.0424 (12)	0.0060 (10)	0.0100 (11)	0.0015 (9)
C7	0.0418 (14)	0.0364 (11)	0.0418 (11)	−0.0014 (10)	0.0053 (9)	0.0003 (9)
C8	0.0427 (13)	0.0362 (11)	0.0357 (11)	−0.0038 (9)	−0.0014 (9)	0.0027 (8)
C9	0.0463 (15)	0.0355 (11)	0.0378 (11)	−0.0051 (9)	0.0004 (10)	0.0036 (8)
C10	0.0428 (14)	0.0422 (12)	0.0391 (11)	−0.0053 (10)	−0.0038 (9)	0.0042 (9)
C11	0.0391 (13)	0.0406 (11)	0.0337 (11)	0.0012 (10)	0.0025 (9)	0.0042 (8)
C12	0.0390 (13)	0.0428 (11)	0.0350 (11)	0.0039 (10)	0.0040 (9)	0.0054 (9)
C13	0.0561 (16)	0.0453 (12)	0.0478 (13)	0.0090 (11)	0.0097 (12)	0.0138 (10)
C14	0.0571 (17)	0.0631 (16)	0.0413 (13)	0.0211 (13)	0.0025 (12)	0.0134 (11)
C15	0.0471 (16)	0.0672 (16)	0.0438 (13)	0.0075 (12)	−0.0066 (11)	0.0018 (11)
C16	0.0488 (15)	0.0485 (13)	0.0451 (12)	−0.0022 (11)	−0.0019 (10)	0.0041 (10)

S1—C7	1.736 (2)	C10—C11	1.445 (3)
S1—C8	1.746 (2)	C11—C16	1.397 (3)
S2—C7	1.623 (2)	C11—C12	1.402 (3)
O1—C9	1.216 (3)	C12—C13	1.384 (3)
O2—C12	1.359 (3)	C13—C14	1.378 (3)
O2—H2A	0.8200	C14—C15	1.371 (3)
N1—C7	1.381 (3)	C15—C16	1.367 (3)
N1—C9	1.393 (3)	C2—H2	0.9300
N1—C1	1.448 (3)	C3—H3	0.9300
C1—C6	1.375 (3)	C4—H4	0.9300
C1—C2	1.373 (3)	C5—H5	0.9300
C2—C3	1.384 (3)	C6—H6	0.9300
C3—C4	1.371 (3)	C10—H10	0.9300
C4—C5	1.374 (3)	C13—H13	0.9300
C5—C6	1.384 (3)	C14—H14	0.9300
C8—C9	1.479 (3)	C15—H15	0.9300
C8—C10	1.344 (3)	C16—H16	0.9300
C7—S1—C8	93.20 (10)	C11—C12—C13	120.7 (2)
C12—O2—H2A	109.00	O2—C12—C11	118.06 (18)
C1—N1—C9	121.85 (17)	C12—C13—C14	120.1 (2)
C7—N1—C9	116.78 (17)	C13—C14—C15	120.5 (2)
C1—N1—C7	121.37 (16)	C14—C15—C16	119.5 (2)
N1—C1—C6	119.07 (18)	C11—C16—C15	122.4 (2)
C2—C1—C6	121.6 (2)	C1—C2—H2	121.00
N1—C1—C2	119.28 (19)	C3—C2—H2	121.00
C1—C2—C3	118.9 (2)	C2—C3—H3	120.00
C2—C3—C4	120.1 (2)	C4—C3—H3	120.00
C3—C4—C5	120.5 (2)	C3—C4—H4	120.00
C4—C5—C6	120.1 (2)	C5—C4—H4	120.00
C1—C6—C5	118.8 (2)	C4—C5—H5	120.00
S1—C7—S2	122.00 (13)	C6—C5—H5	120.00
S1—C7—N1	110.23 (15)	C1—C6—H6	121.00
S2—C7—N1	127.77 (16)	C5—C6—H6	121.00
S1—C8—C9	109.54 (15)	C8—C10—H10	115.00
S1—C8—C10	128.64 (17)	C11—C10—H10	115.00
C9—C8—C10	121.8 (2)	C12—C13—H13	120.00
O1—C9—C8	127.4 (2)	C14—C13—H13	120.00
N1—C9—C8	110.11 (18)	C13—C14—H14	120.00
O1—C9—N1	122.45 (19)	C15—C14—H14	120.00
C8—C10—C11	130.6 (2)	C14—C15—H15	120.00
C10—C11—C16	124.3 (2)	C16—C15—H15	120.00
C12—C11—C16	116.97 (19)	C11—C16—H16	119.00
C10—C11—C12	118.71 (19)	C15—C16—H16	119.00
O2—C12—C13	121.3 (2)
C8—S1—C7—S2	−179.12 (15)	C3—C4—C5—C6	0.3 (4)
C8—S1—C7—N1	1.29 (16)	C4—C5—C6—C1	−1.1 (3)
C7—S1—C8—C9	0.95 (16)	S1—C8—C9—O1	177.26 (19)
C7—S1—C8—C10	−177.2 (2)	S1—C8—C9—N1	−2.9 (2)
C7—N1—C1—C2	−99.9 (2)	C10—C8—C9—O1	−4.5 (4)
C7—N1—C1—C6	78.9 (3)	C10—C8—C9—N1	175.33 (19)
C9—N1—C1—C2	80.0 (3)	S1—C8—C10—C11	−1.9 (4)
C9—N1—C1—C6	−101.2 (2)	C9—C8—C10—C11	−179.8 (2)
C1—N1—C7—S1	176.46 (14)	C8—C10—C11—C12	172.8 (2)
C1—N1—C7—S2	−3.1 (3)	C8—C10—C11—C16	−8.2 (4)
C9—N1—C7—S1	−3.5 (2)	C10—C11—C12—O2	−3.0 (3)
C9—N1—C7—S2	176.98 (17)	C10—C11—C12—C13	177.9 (2)
C1—N1—C9—O1	4.1 (3)	C16—C11—C12—O2	177.90 (19)
C1—N1—C9—C8	−175.75 (17)	C16—C11—C12—C13	−1.2 (3)
C7—N1—C9—O1	−176.0 (2)	C10—C11—C16—C15	−178.6 (2)
C7—N1—C9—C8	4.2 (2)	C12—C11—C16—C15	0.5 (3)
N1—C1—C2—C3	178.1 (2)	O2—C12—C13—C14	−178.7 (2)
C6—C1—C2—C3	−0.7 (3)	C11—C12—C13—C14	0.3 (3)
N1—C1—C6—C5	−177.6 (2)	C12—C13—C14—C15	1.3 (3)
C2—C1—C6—C5	1.3 (3)	C13—C14—C15—C16	−2.0 (3)
C1—C2—C3—C4	−0.1 (3)	C14—C15—C16—C11	1.1 (3)
C2—C3—C4—C5	0.2 (4)

D—H···A	D—H	H···A	D···A	D—H···A
C16—H16···S1	0.93	2.50	3.213 (2)	133
O2—H2A···O1i	0.82	1.97	2.767 (2)	163
C10—H10···O2i	0.93	2.49	3.375 (3)	160
C2—H2···CgBii	0.93	2.91	3.774 (2)	155
C14—H14···CgBiii	0.93	2.91	3.515 (2)	124

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C16—H16⋯S1	0.93	2.50	3.213 (2)	133
O2—H2A⋯O1i	0.82	1.97	2.767 (2)	163
C10—H10⋯O2i	0.93	2.49	3.375 (3)	160
C2—H2⋯CgBii	0.93	2.91	3.774 (2)	155
C14—H14⋯CgBiii	0.93	2.91	3.515 (2)	124

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