2-(4-Fluoro-phen-yl)-3-[5-(4-nitro-phen-yl)-1,3,4-thia-diazol-2-yl]-1,3-thia-zolidin-4-one.

In the title compound, C(17)H(11)FN(4)O(3)S(2), the five-membered thia-zolidinone and thia-diazole rings are almost planar, with r.m.s. deviations of 0.017 and 0.0019 Å, respectively. The 4-fluoro-phenyl ring is almost perpendicular to the thia-diazole ring, making a dihedral angle of 89.5 (3)°. The 4-nitro-phenyl ring is nearly coplanar with the thia-diazole ring, the dihedral angle being 7.9 (3)°. The crystal structure is stabilized by two inter-molecular C-H⋯O hydrogen bonds.

Related literature

For the chemical and pharmaceutical properties of thia­diazole derivatives, see: Arun et al. (1999 ▶); Chen et al. (2000 ▶); Kidwai et al. (2000 ▶); Vicentini et al. (1998 ▶); Wasfy et al. (1996 ▶). For a related structure, see: Wan et al. (2008 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C17H11FN4O3S2

M = 402.44

Triclinic,

a = 7.2360 (14) Å

b = 9.1340 (18) Å

c = 14.464 (3) Å

α = 71.67 (2)°

β = 87.16 (3)°

γ = 75.69 (2)°

V = 878.9 (3) Å3

Z = 2

Mo Kα radiation

μ = 0.34 mm−1

T = 293 K

0.30 × 0.10 × 0.05 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

Absorption correction: ψ scan (North et al., 1968 ▶) T min = 0.905, T max = 0.983

3470 measured reflections

3195 independent reflections

1330 reflections with I > 2σ(I)

R int = 0.036

3 standard reflections every 200 reflections intensity decay: 1%

Refinement

R[F 2 > 2σ(F 2)] = 0.060

wR(F 2) = 0.086

S = 0.96

3195 reflections

244 parameters

2 restraints

H-atom parameters constrained

Δρmax = 0.24 e Å−3

Δρmin = −0.16 e Å−3

Data collection: CAD-4 EXPRESS (Enraf-Nonius, 1989 ▶); cell refinement: CAD-4 EXPRESS; 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 (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810023354/pv2286sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810023354/pv2286Isup2.hkl

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

C17H11FN4O3S2	Z = 2
Mr = 402.44	F(000) = 412
Triclinic, P1	Dx = 1.521 Mg m−3
Hall symbol: -P 1	Melting point = 468–469 K
a = 7.2360 (14) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.1340 (18) Å	Cell parameters from 25 reflections
c = 14.464 (3) Å	θ = 8–12°
α = 71.67 (2)°	µ = 0.34 mm−1
β = 87.16 (3)°	T = 293 K
γ = 75.69 (2)°	Plate, colorless
V = 878.9 (3) Å3	0.30 × 0.10 × 0.05 mm

Enraf–Nonius CAD-4 diffractometer	1330 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.036
graphite	θmax = 25.3°, θmin = 1.5°
ω/2θ scans	h = 0→8
Absorption correction: ψ scan (North et al., 1968)	k = −10→10
Tmin = 0.905, Tmax = 0.983	l = −17→17
3470 measured reflections	3 standard reflections every 200 reflections
3195 independent reflections	intensity decay: 1%

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)] = 0.060	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.086	H-atom parameters constrained
S = 0.96	w = 1/[σ2(Fo2) + (0.010P)2] where P = (Fo2 + 2Fc2)/3
3195 reflections	(Δ/σ)max < 0.001
244 parameters	Δρmax = 0.24 e Å−3
2 restraints	Δρmin = −0.16 e Å−3

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	−0.38553 (16)	0.40768 (16)	0.33761 (10)	0.1076 (5)
S2	0.04152 (14)	0.21307 (12)	0.06830 (8)	0.0692 (3)
F	0.4006 (4)	0.1694 (3)	0.5770 (2)	0.1367 (11)
O1	−0.2824 (4)	0.1676 (4)	0.1585 (2)	0.0930 (11)
O2	0.9132 (6)	0.1639 (5)	−0.2536 (3)	0.1480 (18)
O3	0.7277 (6)	0.0551 (5)	−0.2946 (3)	0.1517 (18)
N1	−0.1477 (4)	0.3266 (4)	0.2108 (2)	0.0661 (9)
N2	0.1157 (5)	0.4161 (3)	0.1383 (2)	0.0683 (10)
N3	0.2535 (5)	0.3935 (4)	0.0692 (2)	0.0762 (11)
N4	0.7610 (8)	0.1341 (6)	−0.2506 (4)	0.1108 (18)
C1	0.0664 (6)	0.1986 (6)	0.3988 (3)	0.0880 (15)
H1A	0.0117	0.1288	0.3813	0.106*
C2	0.2070 (8)	0.1378 (7)	0.4716 (4)	0.1105 (19)
H2B	0.2581	0.0290	0.4985	0.133*
C3	0.2620 (7)	0.2377 (9)	0.4996 (4)	0.105 (2)
C4	0.2190 (8)	0.4000 (8)	0.4583 (4)	0.1027 (19)
H4A	0.2763	0.4664	0.4780	0.123*
C5	0.0798 (7)	0.4547 (6)	0.3836 (4)	0.0941 (16)
H5A	0.0356	0.5637	0.3538	0.113*
C6	0.0073 (6)	0.3531 (6)	0.3532 (3)	0.0699 (12)
C7	−0.1554 (5)	0.4201 (4)	0.2769 (3)	0.0673 (12)
H7A	−0.1582	0.5308	0.2398	0.081*
C8	−0.4389 (6)	0.2787 (5)	0.2801 (3)	0.0997 (14)
H8A	−0.4480	0.1799	0.3289	0.120*
H8B	−0.5612	0.3270	0.2454	0.120*
C9	−0.2846 (7)	0.2443 (6)	0.2088 (4)	0.0880 (16)
C10	−0.0012 (5)	0.3287 (4)	0.1446 (3)	0.0618 (11)
C11	0.2339 (6)	0.2965 (5)	0.0283 (3)	0.0618 (12)
C12	0.3617 (6)	0.2569 (5)	−0.0445 (3)	0.0707 (12)
C13	0.3348 (6)	0.1556 (5)	−0.0957 (3)	0.0773 (13)
H13A	0.2304	0.1107	−0.0828	0.093*
C14	0.4619 (7)	0.1221 (5)	−0.1651 (3)	0.0899 (15)
H14A	0.4381	0.0628	−0.2029	0.108*
C15	0.6262 (7)	0.1787 (5)	−0.1773 (3)	0.0748 (13)
C16	0.6601 (6)	0.2724 (6)	−0.1301 (3)	0.0924 (15)
H16A	0.7680	0.3127	−0.1423	0.111*
C17	0.5285 (6)	0.3094 (5)	−0.0611 (3)	0.0749 (13)
H17A	0.5540	0.3712	−0.0254	0.090*

	U11	U22	U33	U12	U13	U23
S1	0.0478 (7)	0.1601 (13)	0.1320 (12)	−0.0182 (8)	0.0108 (8)	−0.0759 (11)
S2	0.0633 (7)	0.0719 (8)	0.0791 (8)	−0.0314 (6)	−0.0064 (6)	−0.0202 (6)
F	0.130 (3)	0.152 (3)	0.127 (2)	−0.024 (2)	−0.024 (2)	−0.047 (2)
O1	0.080 (2)	0.109 (3)	0.109 (3)	−0.049 (2)	0.001 (2)	−0.040 (2)
O2	0.150 (4)	0.155 (4)	0.172 (4)	−0.060 (3)	0.080 (4)	−0.090 (3)
O3	0.139 (4)	0.198 (4)	0.144 (4)	−0.012 (3)	0.007 (3)	−0.113 (3)
N1	0.051 (2)	0.087 (3)	0.063 (2)	−0.024 (2)	−0.0025 (19)	−0.021 (2)
N2	0.069 (2)	0.061 (2)	0.078 (3)	−0.015 (2)	−0.004 (2)	−0.027 (2)
N3	0.074 (3)	0.089 (3)	0.072 (3)	−0.035 (2)	0.010 (2)	−0.025 (2)
N4	0.112 (4)	0.113 (4)	0.083 (4)	0.012 (4)	0.017 (4)	−0.029 (3)
C1	0.069 (3)	0.091 (4)	0.076 (4)	−0.004 (3)	−0.002 (3)	0.002 (3)
C2	0.099 (5)	0.114 (5)	0.092 (5)	−0.009 (4)	0.001 (3)	−0.008 (4)
C3	0.066 (4)	0.160 (7)	0.091 (5)	−0.011 (5)	−0.013 (3)	−0.054 (5)
C4	0.077 (4)	0.151 (5)	0.119 (5)	−0.045 (4)	0.019 (4)	−0.085 (5)
C5	0.066 (3)	0.126 (5)	0.111 (4)	−0.028 (3)	0.027 (3)	−0.065 (4)
C6	0.047 (3)	0.106 (4)	0.058 (3)	−0.020 (3)	0.004 (2)	−0.028 (3)
C7	0.063 (3)	0.079 (3)	0.068 (3)	−0.023 (3)	0.004 (2)	−0.029 (3)
C8	0.076 (3)	0.146 (4)	0.084 (4)	−0.051 (3)	0.008 (3)	−0.027 (3)
C9	0.070 (3)	0.110 (5)	0.080 (4)	−0.037 (3)	−0.004 (3)	−0.011 (3)
C10	0.046 (3)	0.068 (3)	0.073 (3)	−0.013 (2)	−0.013 (2)	−0.024 (3)
C11	0.072 (3)	0.066 (3)	0.061 (3)	−0.043 (2)	0.004 (2)	−0.020 (2)
C12	0.076 (3)	0.067 (3)	0.066 (3)	−0.025 (3)	−0.006 (3)	−0.009 (3)
C13	0.081 (3)	0.064 (3)	0.093 (4)	−0.017 (3)	−0.003 (3)	−0.032 (3)
C14	0.120 (5)	0.079 (3)	0.082 (4)	−0.030 (3)	−0.020 (3)	−0.032 (3)
C15	0.079 (4)	0.066 (3)	0.071 (4)	−0.027 (3)	−0.001 (3)	−0.002 (3)
C16	0.073 (4)	0.111 (4)	0.096 (4)	−0.024 (3)	−0.008 (3)	−0.033 (3)
C17	0.066 (3)	0.081 (3)	0.087 (4)	−0.036 (3)	−0.002 (3)	−0.025 (3)

S1—C8	1.761 (4)	C4—C5	1.397 (6)
S1—C7	1.855 (3)	C4—H4A	0.9300
S2—C10	1.723 (4)	C5—C6	1.360 (5)
S2—C11	1.738 (3)	C5—H5A	0.9300
F—C3	1.418 (5)	C6—C7	1.526 (5)
O1—C9	1.155 (5)	C7—H7A	0.9800
O2—N4	1.194 (5)	C8—C9	1.525 (5)
O3—N4	1.172 (5)	C8—H8A	0.9700
N1—C9	1.390 (5)	C8—H8B	0.9700
N1—C10	1.392 (4)	C11—C12	1.439 (5)
N1—C7	1.460 (4)	C12—C17	1.389 (5)
N2—C10	1.281 (4)	C12—C13	1.406 (4)
N2—N3	1.401 (4)	C13—C14	1.381 (5)
N3—C11	1.248 (4)	C13—H13A	0.9300
N4—C15	1.489 (6)	C14—C15	1.391 (5)
C1—C6	1.324 (5)	C14—H14A	0.9300
C1—C2	1.382 (6)	C15—C16	1.321 (5)
C1—H1A	0.9300	C16—C17	1.405 (5)
C2—C3	1.257 (6)	C16—H16A	0.9300
C2—H2B	0.9300	C17—H17A	0.9300
C3—C4	1.373 (6)
C8—S1—C7	95.25 (18)	C9—C8—S1	110.5 (3)
C10—S2—C11	86.21 (19)	C9—C8—H8A	109.6
C9—N1—C10	120.0 (4)	S1—C8—H8A	109.6
C9—N1—C7	122.6 (4)	C9—C8—H8B	109.6
C10—N1—C7	117.3 (3)	S1—C8—H8B	109.6
C10—N2—N3	110.6 (3)	H8A—C8—H8B	108.1
C11—N3—N2	114.2 (3)	O1—C9—N1	124.8 (5)
O3—N4—O2	121.2 (6)	O1—C9—C8	126.7 (5)
O3—N4—C15	120.6 (6)	N1—C9—C8	108.5 (4)
O2—N4—C15	117.5 (6)	N2—C10—N1	121.3 (4)
C6—C1—C2	122.1 (5)	N2—C10—S2	115.0 (3)
C6—C1—H1A	118.9	N1—C10—S2	123.6 (3)
C2—C1—H1A	118.9	N3—C11—C12	122.5 (4)
C3—C2—C1	116.3 (6)	N3—C11—S2	113.9 (3)
C3—C2—H2B	121.8	C12—C11—S2	123.6 (3)
C1—C2—H2B	121.8	C17—C12—C13	116.9 (4)
C2—C3—C4	128.0 (6)	C17—C12—C11	119.8 (4)
C2—C3—F	114.2 (7)	C13—C12—C11	123.2 (4)
C4—C3—F	117.4 (6)	C14—C13—C12	120.7 (4)
C3—C4—C5	112.7 (5)	C14—C13—H13A	119.7
C3—C4—H4A	123.7	C12—C13—H13A	119.7
C5—C4—H4A	123.7	C13—C14—C15	118.8 (4)
C6—C5—C4	121.9 (5)	C13—C14—H14A	120.6
C6—C5—H5A	119.1	C15—C14—H14A	120.6
C4—C5—H5A	119.1	C16—C15—C14	122.9 (5)
C1—C6—C5	118.4 (5)	C16—C15—N4	120.7 (5)
C1—C6—C7	121.8 (5)	C14—C15—N4	116.4 (5)
C5—C6—C7	119.4 (5)	C15—C16—C17	118.2 (5)
N1—C7—C6	113.5 (3)	C15—C16—H16A	120.9
N1—C7—S1	102.9 (2)	C17—C16—H16A	120.9
C6—C7—S1	109.6 (3)	C12—C17—C16	122.3 (4)
N1—C7—H7A	110.2	C12—C17—H17A	118.9
C6—C7—H7A	110.2	C16—C17—H17A	118.9
S1—C7—H7A	110.2
C10—N2—N3—C11	0.7 (5)	N3—N2—C10—S2	−0.5 (4)
C6—C1—C2—C3	7.2 (8)	C9—N1—C10—N2	173.0 (4)
C1—C2—C3—C4	−9.5 (9)	C7—N1—C10—N2	−3.8 (5)
C1—C2—C3—F	177.5 (4)	C9—N1—C10—S2	−8.7 (5)
C2—C3—C4—C5	7.9 (9)	C7—N1—C10—S2	174.5 (3)
F—C3—C4—C5	−179.4 (4)	C11—S2—C10—N2	0.2 (3)
C3—C4—C5—C6	−3.8 (7)	C11—S2—C10—N1	−178.2 (3)
C2—C1—C6—C5	−4.0 (7)	N2—N3—C11—C12	−179.7 (3)
C2—C1—C6—C7	−176.6 (4)	N2—N3—C11—S2	−0.6 (5)
C4—C5—C6—C1	2.5 (6)	C10—S2—C11—N3	0.2 (3)
C4—C5—C6—C7	175.2 (4)	C10—S2—C11—C12	179.4 (4)
C9—N1—C7—C6	113.8 (4)	N3—C11—C12—C17	9.3 (6)
C10—N1—C7—C6	−69.5 (4)	S2—C11—C12—C17	−169.8 (3)
C9—N1—C7—S1	−4.6 (4)	N3—C11—C12—C13	−175.9 (4)
C10—N1—C7—S1	172.1 (3)	S2—C11—C12—C13	5.0 (6)
C1—C6—C7—N1	−41.7 (5)	C17—C12—C13—C14	−5.3 (6)
C5—C6—C7—N1	145.9 (4)	C11—C12—C13—C14	179.8 (4)
C1—C6—C7—S1	72.8 (5)	C12—C13—C14—C15	5.7 (7)
C5—C6—C7—S1	−99.7 (4)	C13—C14—C15—C16	−4.8 (7)
C8—S1—C7—N1	3.4 (3)	C13—C14—C15—N4	177.9 (4)
C8—S1—C7—C6	−117.7 (3)	O3—N4—C15—C16	−177.6 (5)
C7—S1—C8—C9	−2.0 (3)	O2—N4—C15—C16	11.9 (8)
C10—N1—C9—O1	4.3 (7)	O3—N4—C15—C14	−0.2 (7)
C7—N1—C9—O1	−179.1 (5)	O2—N4—C15—C14	−170.8 (5)
C10—N1—C9—C8	−173.2 (3)	C14—C15—C16—C17	3.3 (7)
C7—N1—C9—C8	3.4 (5)	N4—C15—C16—C17	−179.5 (4)
S1—C8—C9—O1	−177.7 (5)	C13—C12—C17—C16	3.9 (6)
S1—C8—C9—N1	−0.2 (5)	C11—C12—C17—C16	179.0 (4)
N3—N2—C10—N1	177.9 (3)	C15—C16—C17—C12	−2.9 (7)

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5A···O2i	0.93	2.56	3.411 (7)	152
C13—H13A···S2	0.93	2.81	3.184 (5)	106
C14—H14A···O1ii	0.93	2.52	3.198 (6)	130

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5A⋯O2i	0.93	2.56	3.411 (7)	152
C14—H14A⋯O1ii	0.93	2.52	3.198 (6)	130

Symmetry codes: (i) ; (ii) .