(Z)-5-(4-Fluoro-benzyl-idene)-1,3-thia-zolidine-2,4-dione.

In the title compound, C(10)H(6)FNO(2)S, the benzene and thia-zolidine rings make a dihedral angle of 7.52 (3)°. Intra-molecular C-H⋯O and C-H⋯S hydrogen bonds result in the formation of nearly planar five- and six-membered rings; the adjacent rings are nearly coplanar. In the crystal structure, inter-molecular N-H⋯O hydrogen bonds link the mol-ecules.

Related literature

For general background, see: Barreca et al. (2002 ▶); Botti et al. (1996 ▶). For a related structure, see: Guo et al. (2006 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C10H6FNO2S

M = 223.22

Orthorhombic,

a = 26.519 (5) Å

b = 36.509 (7) Å

c = 3.8490 (8) Å

V = 3726.6 (13) Å3

Z = 16

Mo Kα radiation

μ = 0.34 mm−1

T = 294 (2) K

0.30 × 0.10 × 0.10 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

Absorption correction: ψ scan (North et al., 1968 ▶) T min = 0.905, T max = 0.967

2087 measured reflections

1059 independent reflections

790 reflections with I > 2σ(I)

R int = 0.042

3 standard reflections frequency: 120 min intensity decay: none

Refinement

R[F 2 > 2σ(F 2)] = 0.053

wR(F 2) = 0.121

S = 1.04

1059 reflections

136 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.38 e Å−3

Δρmin = −0.66 e Å−3

Absolute structure: Flack (1983 ▶), no Friedel pairs

Flack parameter: 0.0 (2)

Data collection: CAD-4 Software (Enraf–Nonius, 1989 ▶); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Siemens, 1996 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536807068316/hk2407sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807068316/hk2407Isup2.hkl

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

C10H6FNO2S	F000 = 1824
Mr = 223.22	Dx = 1.591 Mg m−3
Orthorhombic, Fdd2	Mo Kα radiation λ = 0.71073 Å
Hall symbol: F 2 -2d	Cell parameters from 25 reflections
a = 26.519 (5) Å	θ = 9–13º
b = 36.509 (7) Å	µ = 0.34 mm−1
c = 3.8490 (8) Å	T = 294 (2) K
V = 3726.6 (13) Å3	Block, colorles
Z = 16	0.30 × 0.10 × 0.10 mm

Enraf–Nonius CAD-4 diffractometer	Rint = 0.042
Radiation source: fine-focus sealed tube	θmax = 26.0º
Monochromator: graphite	θmin = 1.9º
T = 294(2) K	h = 0→32
ω/2θ scans	k = 0→44
Absorption correction: ψ scan(North et al., 1968)	l = −4→0
Tmin = 0.905, Tmax = 0.967	3 standard reflections
2087 measured reflections	every 120 min
1059 independent reflections	intensity decay: none
790 reflections with I > 2σ(I)

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.053	w = 1/[σ2(Fo2) + (0.05P)2 + 3P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.121	(Δ/σ)max < 0.001
S = 1.04	Δρmax = 0.38 e Å−3
1059 reflections	Δρmin = −0.66 e Å−3
136 parameters	Extinction correction: none
1 restraint	Absolute structure: Flack (1983), no Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.0 (2)
Secondary atom site location: difference Fourier map

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
S	0.08943 (4)	−0.00189 (3)	−0.0089 (5)	0.0379 (3)
F	−0.06109 (11)	0.13395 (8)	0.6207 (12)	0.0681 (12)
O1	0.13745 (13)	−0.05739 (9)	−0.3062 (14)	0.0619 (12)
O2	0.21942 (10)	0.03754 (8)	0.2142 (14)	0.0493 (10)
N	0.18501 (14)	−0.01228 (9)	−0.0627 (14)	0.0425 (11)
H0A	0.2136	−0.0219	−0.1150	0.051*
C1	−0.01787 (17)	0.11646 (12)	0.5430 (15)	0.0416 (12)
C2	0.02675 (18)	0.13443 (12)	0.5921 (16)	0.0484 (15)
H2A	0.0273	0.1584	0.6744	0.058*
C3	0.07078 (19)	0.11621 (11)	0.5166 (17)	0.0444 (13)
H3A	0.1015	0.1278	0.5559	0.053*
C4	0.07035 (16)	0.08082 (10)	0.3826 (13)	0.0346 (11)
C5	0.02378 (16)	0.06382 (12)	0.3314 (15)	0.0400 (12)
H5A	0.0225	0.0402	0.2421	0.048*
C6	−0.02016 (15)	0.08195 (12)	0.4125 (16)	0.0452 (14)
H6A	−0.0512	0.0707	0.3782	0.054*
C7	0.11827 (16)	0.06366 (11)	0.3095 (14)	0.0352 (10)
H7A	0.1462	0.0772	0.3782	0.042*
C8	0.12929 (15)	0.03151 (11)	0.1597 (14)	0.0317 (10)
C9	0.18224 (17)	0.02026 (11)	0.1107 (15)	0.0370 (12)
C10	0.14053 (17)	−0.02927 (12)	−0.1510 (17)	0.0450 (13)

	U11	U22	U33	U12	U13	U23
S	0.0303 (5)	0.0391 (5)	0.0444 (6)	−0.0005 (4)	0.0015 (7)	−0.0028 (6)
F	0.0400 (16)	0.0705 (18)	0.094 (3)	0.0212 (14)	0.003 (2)	−0.024 (2)
O1	0.058 (2)	0.0465 (17)	0.081 (3)	0.0105 (16)	0.000 (3)	−0.026 (2)
O2	0.0267 (16)	0.0444 (16)	0.077 (3)	0.0002 (12)	−0.0039 (19)	0.001 (2)
N	0.0295 (18)	0.0403 (18)	0.058 (3)	0.0068 (15)	0.001 (2)	0.001 (2)
C1	0.033 (2)	0.051 (2)	0.041 (3)	0.012 (2)	0.003 (2)	−0.009 (3)
C2	0.047 (3)	0.042 (2)	0.056 (4)	0.012 (2)	−0.009 (3)	−0.018 (3)
C3	0.047 (3)	0.036 (2)	0.050 (3)	−0.0028 (19)	−0.002 (3)	−0.007 (3)
C4	0.031 (2)	0.036 (2)	0.036 (3)	0.0030 (17)	−0.002 (2)	−0.002 (2)
C5	0.035 (2)	0.038 (2)	0.047 (3)	0.0012 (17)	−0.001 (2)	−0.006 (2)
C6	0.0209 (18)	0.056 (3)	0.058 (4)	−0.0019 (18)	0.007 (2)	−0.018 (3)
C7	0.030 (2)	0.042 (2)	0.033 (3)	−0.0057 (17)	0.000 (2)	0.008 (2)
C8	0.024 (2)	0.040 (2)	0.031 (3)	0.0007 (16)	−0.003 (2)	0.009 (2)
C9	0.032 (2)	0.037 (2)	0.042 (3)	0.0039 (18)	−0.001 (2)	0.011 (2)
C10	0.038 (2)	0.042 (2)	0.055 (4)	0.0065 (19)	−0.002 (3)	0.002 (3)

S—C8	1.739 (4)	C2—H2A	0.9300
S—C10	1.770 (5)	C3—C4	1.391 (6)
F—C1	1.346 (5)	C3—H3A	0.9300
O1—C10	1.191 (6)	C4—C5	1.396 (6)
O2—C9	1.237 (5)	C4—C7	1.445 (6)
N—C9	1.364 (6)	C5—C6	1.376 (6)
N—C10	1.375 (6)	C5—H5A	0.9300
N—H0A	0.8600	C6—H6A	0.9300
C1—C6	1.358 (6)	C7—C8	1.340 (6)
C1—C2	1.366 (7)	C7—H7A	0.9300
C2—C3	1.375 (6)	C8—C9	1.475 (6)
C8—S—C10	92.6 (2)	C6—C5—H5A	119.9
C9—N—C10	117.9 (4)	C4—C5—H5A	119.9
C9—N—H0A	121.1	C1—C6—C5	119.5 (4)
C10—N—H0A	121.1	C1—C6—H6A	120.3
F—C1—C6	119.0 (4)	C5—C6—H6A	120.3
F—C1—C2	118.6 (4)	C8—C7—C4	131.0 (4)
C6—C1—C2	122.4 (4)	C8—C7—H7A	114.5
C1—C2—C3	118.3 (4)	C4—C7—H7A	114.5
C1—C2—H2A	120.9	C7—C8—C9	120.4 (4)
C3—C2—H2A	120.9	C7—C8—S	129.9 (3)
C2—C3—C4	121.4 (4)	C9—C8—S	109.6 (3)
C2—C3—H3A	119.3	O2—C9—N	124.0 (4)
C4—C3—H3A	119.3	O2—C9—C8	125.1 (4)
C3—C4—C5	118.2 (4)	N—C9—C8	110.9 (4)
C3—C4—C7	117.9 (4)	O1—C10—N	124.9 (4)
C5—C4—C7	123.9 (4)	O1—C10—S	126.1 (4)
C6—C5—C4	120.2 (4)	N—C10—S	109.0 (3)
F—C1—C2—C3	179.1 (5)	C4—C7—C8—S	0.6 (9)
C6—C1—C2—C3	−2.2 (9)	C10—S—C8—C7	177.2 (5)
C1—C2—C3—C4	2.1 (9)	C10—S—C8—C9	−1.5 (4)
C2—C3—C4—C5	−1.0 (8)	C10—N—C9—O2	177.5 (5)
C2—C3—C4—C7	179.8 (5)	C10—N—C9—C8	−1.9 (6)
C3—C4—C5—C6	0.0 (8)	C7—C8—C9—O2	3.9 (8)
C7—C4—C5—C6	179.1 (5)	S—C8—C9—O2	−177.2 (4)
F—C1—C6—C5	179.8 (5)	C7—C8—C9—N	−176.7 (4)
C2—C1—C6—C5	1.2 (9)	S—C8—C9—N	2.2 (5)
C4—C5—C6—C1	−0.1 (9)	C9—N—C10—O1	178.9 (6)
C3—C4—C7—C8	−174.7 (5)	C9—N—C10—S	0.7 (6)
C5—C4—C7—C8	6.3 (9)	C8—S—C10—O1	−177.6 (6)
C4—C7—C8—C9	179.3 (5)	C8—S—C10—N	0.6 (5)

D—H···A	D—H	H···A	D···A	D—H···A
N—H0A···O2i	0.86	1.98	2.830 (5)	171
C5—H5A···S	0.93	2.54	3.241 (5)	133
C7—H7A···O2	0.93	2.50	2.870 (5)	104

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N—H0A⋯O2i	0.86	1.98	2.830 (5)	171
C5—H5A⋯S	0.93	2.54	3.241 (5)	133
C7—H7A⋯O2	0.93	2.50	2.870 (5)	104

Symmetry code: (i) .