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

The title compound, C(18)H(14)FN(3)O(2)S(2), was synthesized by the reaction of 5-(4-fluoro-phen-yl)-N-(4-methoxy-benzyl-idene)-1,3,4-thia-diazol-2-amine and mercaptoacetic acid. The thia-zolidinone ring adopts a twist conformation. The 4-methoxy-phenyl ring is almost perpendicular to the thia-diazole ring, making a dihedral angle of 88.4 (3)°. The 4-fluoro-phenyl ring is nearly coplanar with the thia-diazole ring, the dihedral angle being 6.8 (3)°. The crystal structure involves C-H⋯N, C-H⋯O and C-H⋯S hydrogen bonds.

Related literature

For related literature, see: Arun et al. (1999 ▶); Chen et al. (2000 ▶); Kidwai et al. (2000 ▶); Vicentini et al. (1998 ▶); Wasfy et al. (1996 ▶); Allen et al. (1987 ▶).

Experimental

Crystal data

C18H14FN3O2S2

M = 387.44

Triclinic,

a = 6.4550 (13) Å

b = 8.9200 (18) Å

c = 16.483 (3) Å

α = 75.78 (3)°

β = 82.44 (3)°

γ = 71.11 (3)°

V = 869.0 (3) Å3

Z = 2

Mo Kα radiation

μ = 0.34 mm−1

T = 298 (2) K

0.10 × 0.05 × 0.05 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

Absorption correction: ψ scan (North et al., 1968 ▶) T min = 0.967, T max = 0.984

3421 measured reflections

3120 independent reflections

2054 reflections with I > 2σ(I)

R int = 0.023

3 standard reflections every 200 reflections intensity decay: none

Refinement

R[F 2 > 2σ(F 2)] = 0.070

wR(F 2) = 0.186

S = 1.00

3120 reflections

229 parameters

48 restraints

H-atom parameters constrained

Δρmax = 0.41 e Å−3

Δρmin = −0.52 e Å−3

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 (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808019089/at2579sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808019089/at2579Isup2.hkl

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

C18H14FN3O2S2	Z = 2
Mr = 387.44	F000 = 400
Triclinic, P1	Dx = 1.481 Mg m−3
Hall symbol: -P 1	Melting point = 341–345 K
a = 6.4550 (13) Å	Mo Kα radiation λ = 0.71073 Å
b = 8.9200 (18) Å	Cell parameters from 25 reflections
c = 16.483 (3) Å	θ = 9–12º
α = 75.78 (3)º	µ = 0.34 mm−1
β = 82.44 (3)º	T = 298 (2) K
γ = 71.11 (3)º	Block, colourless
V = 869.0 (3) Å3	0.10 × 0.05 × 0.05 mm

Enraf–Nonius CAD-4 diffractometer	Rint = 0.023
Radiation source: fine-focus sealed tube	θmax = 25.2º
Monochromator: graphite	θmin = 1.3º
T = 298(2) K	h = −7→7
ω/2θ scans	k = −10→10
Absorption correction: ψ scan(North et al., 1968)	l = 0→19
Tmin = 0.967, Tmax = 0.984	3 standard reflections
3421 measured reflections	every 200 reflections
3120 independent reflections	intensity decay: none
2054 reflections with I > 2σ(I)

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)] = 0.070	H-atom parameters constrained
wR(F2) = 0.186	w = 1/[σ2(Fo2) + (0.05P)2 + 2.5P] where P = (Fo2 + 2Fc2)/3
S = 1.00	(Δ/σ)max < 0.001
3120 reflections	Δρmax = 0.41 e Å−3
229 parameters	Δρmin = −0.52 e Å−3
48 restraints	Extinction correction: none
Primary atom site location: structure-invariant direct methods

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	0.1232 (3)	1.32787 (19)	0.18123 (10)	0.0698 (5)
S2	0.7085 (2)	0.94841 (16)	0.40097 (8)	0.0525 (4)
F	1.1681 (6)	0.3585 (4)	0.7202 (2)	0.0868 (11)
O1	0.3391 (7)	0.6926 (6)	0.0237 (3)	0.0873 (14)
O2	0.6785 (6)	1.2181 (5)	0.2766 (2)	0.0669 (11)
N1	0.4009 (7)	1.1081 (5)	0.2832 (3)	0.0524 (10)
N2	0.3572 (7)	0.8821 (6)	0.3839 (3)	0.0624 (12)
N3	0.4550 (7)	0.7685 (6)	0.4514 (3)	0.0615 (12)
C1	0.1565 (11)	0.6619 (9)	−0.0019 (4)	0.084 (2)
H1A	0.2071	0.5921	−0.0410	0.126*
H1B	0.0557	0.7626	−0.0281	0.126*
H1C	0.0839	0.6105	0.0462	0.126*
C2	0.2971 (9)	0.7920 (7)	0.0792 (4)	0.0628 (14)
C3	0.0998 (10)	0.8504 (8)	0.1184 (4)	0.0731 (16)
H3B	−0.0205	0.8231	0.1084	0.088*
C4	0.0759 (9)	0.9502 (8)	0.1733 (4)	0.0687 (16)
H4A	−0.0604	0.9869	0.2006	0.082*
C5	0.2469 (8)	0.9971 (7)	0.1889 (3)	0.0550 (12)
C6	0.4424 (11)	0.9355 (10)	0.1499 (5)	0.107 (3)
H6A	0.5630	0.9621	0.1602	0.128*
C7	0.4704 (12)	0.8350 (10)	0.0956 (5)	0.109
H7A	0.6079	0.7959	0.0697	0.131*
C8	0.2051 (8)	1.1190 (6)	0.2422 (3)	0.0544 (13)
H8A	0.0890	1.1042	0.2852	0.065*
C9	0.3907 (10)	1.3489 (8)	0.1783 (4)	0.0770 (18)
H9A	0.4707	1.3304	0.1258	0.092*
H9B	0.3797	1.4573	0.1835	0.092*
C10	0.5063 (9)	1.2245 (7)	0.2508 (3)	0.0567 (13)
C11	0.4717 (8)	0.9827 (6)	0.3532 (3)	0.0505 (12)
C12	0.6418 (8)	0.7842 (6)	0.4677 (3)	0.0470 (11)
C13	0.7762 (8)	0.6774 (6)	0.5357 (3)	0.0480 (11)
C14	0.9628 (9)	0.7058 (7)	0.5547 (3)	0.0608 (14)
H14A	1.0009	0.7966	0.5243	0.073*
C15	1.0908 (10)	0.6009 (7)	0.6181 (4)	0.0668 (15)
H15A	1.2114	0.6223	0.6324	0.080*
C16	1.0368 (9)	0.4640 (7)	0.6596 (3)	0.0613 (15)
C17	0.8542 (10)	0.4310 (7)	0.6425 (3)	0.0647 (15)
H17A	0.8189	0.3390	0.6728	0.078*
C18	0.7262 (9)	0.5372 (6)	0.5799 (3)	0.0584 (14)
H18A	0.6044	0.5156	0.5668	0.070*

	U11	U22	U33	U12	U13	U23
S1	0.0724 (10)	0.0617 (9)	0.0743 (10)	−0.0157 (8)	−0.0163 (8)	−0.0123 (8)
S2	0.0476 (7)	0.0587 (8)	0.0565 (8)	−0.0219 (6)	−0.0011 (6)	−0.0152 (6)
F	0.092 (3)	0.081 (2)	0.075 (2)	−0.008 (2)	−0.022 (2)	−0.0116 (19)
O1	0.085 (3)	0.102 (3)	0.098 (3)	−0.038 (3)	0.013 (3)	−0.059 (3)
O2	0.054 (2)	0.069 (3)	0.081 (3)	−0.0299 (19)	−0.005 (2)	−0.008 (2)
N1	0.052 (2)	0.056 (3)	0.056 (3)	−0.023 (2)	0.000 (2)	−0.017 (2)
N2	0.057 (3)	0.064 (3)	0.069 (3)	−0.029 (2)	−0.007 (2)	−0.003 (2)
N3	0.058 (3)	0.068 (3)	0.063 (3)	−0.028 (2)	−0.007 (2)	−0.008 (2)
C1	0.100 (5)	0.094 (5)	0.075 (4)	−0.038 (4)	−0.012 (4)	−0.032 (4)
C2	0.064 (3)	0.061 (3)	0.067 (3)	−0.015 (3)	−0.002 (3)	−0.027 (3)
C3	0.064 (3)	0.089 (4)	0.077 (4)	−0.026 (3)	0.003 (3)	−0.038 (3)
C4	0.051 (3)	0.090 (4)	0.072 (4)	−0.024 (3)	0.011 (3)	−0.035 (3)
C5	0.050 (3)	0.062 (3)	0.054 (3)	−0.016 (2)	−0.004 (2)	−0.014 (2)
C6	0.062 (4)	0.139 (6)	0.152 (6)	−0.034 (4)	0.011 (4)	−0.096 (5)
C7	0.070	0.148	0.146	−0.040	0.021	−0.105
C8	0.046 (3)	0.059 (3)	0.061 (3)	−0.018 (2)	−0.003 (2)	−0.016 (3)
C9	0.083 (4)	0.081 (4)	0.065 (4)	−0.037 (4)	0.005 (3)	−0.001 (3)
C10	0.055 (3)	0.061 (3)	0.058 (3)	−0.024 (3)	0.008 (3)	−0.017 (3)
C11	0.049 (3)	0.057 (3)	0.051 (3)	−0.021 (2)	0.004 (2)	−0.018 (2)
C12	0.046 (3)	0.047 (3)	0.047 (3)	−0.013 (2)	0.005 (2)	−0.014 (2)
C13	0.042 (3)	0.050 (3)	0.048 (3)	−0.007 (2)	0.006 (2)	−0.016 (2)
C14	0.060 (3)	0.072 (4)	0.057 (3)	−0.028 (3)	0.001 (3)	−0.016 (3)
C15	0.065 (4)	0.075 (4)	0.061 (4)	−0.014 (3)	−0.015 (3)	−0.019 (3)
C16	0.065 (4)	0.059 (3)	0.045 (3)	0.003 (3)	−0.012 (3)	−0.008 (3)
C17	0.074 (4)	0.058 (3)	0.058 (3)	−0.018 (3)	−0.004 (3)	−0.005 (3)
C18	0.060 (3)	0.059 (3)	0.063 (3)	−0.027 (3)	0.000 (3)	−0.017 (3)

S1—C9	1.790 (6)	C4—H4A	0.9300
S1—C8	1.828 (5)	C5—C6	1.349 (8)
S2—C11	1.716 (5)	C5—C8	1.497 (7)
S2—C12	1.741 (5)	C6—C7	1.373 (9)
F—C16	1.359 (6)	C6—H6A	0.9300
O1—C2	1.368 (6)	C7—H7A	0.9300
O1—C1	1.428 (7)	C8—H8A	0.9800
O2—C10	1.221 (6)	C9—C10	1.504 (8)
N1—C10	1.384 (6)	C9—H9A	0.9700
N1—C11	1.402 (6)	C9—H9B	0.9700
N1—C8	1.475 (6)	C12—C13	1.454 (7)
N2—C11	1.309 (6)	C13—C14	1.396 (7)
N2—N3	1.371 (6)	C13—C18	1.396 (7)
N3—C12	1.326 (6)	C14—C15	1.377 (8)
C1—H1A	0.9600	C14—H14A	0.9300
C1—H1B	0.9600	C15—C16	1.373 (8)
C1—H1C	0.9600	C15—H15A	0.9300
C2—C3	1.354 (8)	C16—C17	1.381 (8)
C2—C7	1.371 (8)	C17—C18	1.372 (7)
C3—C4	1.380 (8)	C17—H17A	0.9300
C3—H3B	0.9300	C18—H18A	0.9300
C4—C5	1.373 (7)
C9—S1—C8	93.5 (3)	C5—C8—H8A	109.0
C11—S2—C12	85.8 (2)	S1—C8—H8A	109.0
C2—O1—C1	117.6 (5)	C10—C9—S1	106.9 (4)
C10—N1—C11	122.7 (4)	C10—C9—H9A	110.3
C10—N1—C8	118.0 (4)	S1—C9—H9A	110.3
C11—N1—C8	119.3 (4)	C10—C9—H9B	110.3
C11—N2—N3	110.4 (4)	S1—C9—H9B	110.3
C12—N3—N2	113.4 (4)	H9A—C9—H9B	108.6
O1—C1—H1A	109.5	O2—C10—N1	122.5 (5)
O1—C1—H1B	109.5	O2—C10—C9	125.7 (5)
H1A—C1—H1B	109.5	N1—C10—C9	111.7 (5)
O1—C1—H1C	109.5	N2—C11—N1	119.7 (4)
H1A—C1—H1C	109.5	N2—C11—S2	116.8 (4)
H1B—C1—H1C	109.5	N1—C11—S2	123.4 (4)
C3—C2—O1	125.2 (5)	N3—C12—C13	123.5 (5)
C3—C2—C7	118.1 (6)	N3—C12—S2	113.5 (4)
O1—C2—C7	116.7 (5)	C13—C12—S2	123.0 (4)
C2—C3—C4	120.4 (6)	C14—C13—C18	118.8 (5)
C2—C3—H3B	119.8	C14—C13—C12	121.6 (5)
C4—C3—H3B	119.8	C18—C13—C12	119.5 (5)
C5—C4—C3	122.1 (5)	C15—C14—C13	120.7 (5)
C5—C4—H4A	118.9	C15—C14—H14A	119.7
C3—C4—H4A	118.9	C13—C14—H14A	119.7
C6—C5—C4	116.3 (5)	C16—C15—C14	118.6 (5)
C6—C5—C8	124.1 (5)	C16—C15—H15A	120.7
C4—C5—C8	119.5 (5)	C14—C15—H15A	120.7
C5—C6—C7	122.5 (6)	F—C16—C15	118.2 (5)
C5—C6—H6A	118.7	F—C16—C17	119.3 (6)
C7—C6—H6A	118.7	C15—C16—C17	122.5 (5)
C2—C7—C6	120.5 (6)	C18—C17—C16	118.5 (5)
C2—C7—H7A	119.7	C18—C17—H17A	120.8
C6—C7—H7A	119.7	C16—C17—H17A	120.8
N1—C8—C5	113.5 (4)	C17—C18—C13	120.9 (5)
N1—C8—S1	103.5 (3)	C17—C18—H18A	119.6
C5—C8—S1	112.5 (4)	C13—C18—H18A	119.6
N1—C8—H8A	109.0
C11—N2—N3—C12	−1.9 (6)	S1—C9—C10—O2	−168.3 (5)
C1—O1—C2—C3	7.2 (9)	S1—C9—C10—N1	15.5 (6)
C1—O1—C2—C7	−172.7 (7)	N3—N2—C11—N1	179.5 (4)
O1—C2—C3—C4	−180.0 (6)	N3—N2—C11—S2	1.2 (6)
C7—C2—C3—C4	0.0 (10)	C10—N1—C11—N2	175.9 (5)
C2—C3—C4—C5	1.5 (10)	C8—N1—C11—N2	−3.5 (7)
C3—C4—C5—C6	−2.3 (10)	C10—N1—C11—S2	−5.9 (7)
C3—C4—C5—C8	173.7 (6)	C8—N1—C11—S2	174.7 (4)
C4—C5—C6—C7	1.8 (12)	C12—S2—C11—N2	−0.2 (4)
C8—C5—C6—C7	−174.0 (7)	C12—S2—C11—N1	−178.4 (4)
C3—C2—C7—C6	−0.5 (12)	N2—N3—C12—C13	−179.5 (4)
O1—C2—C7—C6	179.5 (8)	N2—N3—C12—S2	1.8 (6)
C5—C6—C7—C2	−0.4 (14)	C11—S2—C12—N3	−0.9 (4)
C10—N1—C8—C5	104.3 (5)	C11—S2—C12—C13	−179.7 (4)
C11—N1—C8—C5	−76.2 (6)	N3—C12—C13—C14	−174.9 (5)
C10—N1—C8—S1	−17.9 (5)	S2—C12—C13—C14	3.7 (7)
C11—N1—C8—S1	161.6 (4)	N3—C12—C13—C18	9.1 (7)
C6—C5—C8—N1	−28.9 (9)	S2—C12—C13—C18	−172.3 (4)
C4—C5—C8—N1	155.4 (5)	C18—C13—C14—C15	−2.4 (8)
C6—C5—C8—S1	88.3 (7)	C12—C13—C14—C15	−178.4 (5)
C4—C5—C8—S1	−87.4 (6)	C13—C14—C15—C16	2.8 (8)
C9—S1—C8—N1	22.4 (4)	C14—C15—C16—F	177.9 (5)
C9—S1—C8—C5	−100.6 (4)	C14—C15—C16—C17	−2.6 (9)
C8—S1—C9—C10	−22.2 (5)	F—C16—C17—C18	−178.7 (5)
C11—N1—C10—O2	6.3 (8)	C15—C16—C17—C18	1.9 (9)
C8—N1—C10—O2	−174.3 (5)	C16—C17—C18—C13	−1.4 (8)
C11—N1—C10—C9	−177.4 (5)	C14—C13—C18—C17	1.6 (8)
C8—N1—C10—C9	2.1 (7)	C12—C13—C18—C17	177.7 (5)

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6A···N1	0.93	2.60	2.917 (9)	101
C8—H8A···O2i	0.98	2.52	3.233 (7)	129
C14—H14A···S2	0.93	2.74	3.146 (6)	107
C18—H18A···N3	0.93	2.57	2.881 (7)	100

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6A⋯N1	0.93	2.60	2.917 (9)	101
C8—H8A⋯O2i	0.98	2.52	3.233 (7)	129
C14—H14A⋯S2	0.93	2.74	3.146 (6)	107
C18—H18A⋯N3	0.93	2.57	2.881 (7)	100

Symmetry code: (i) .