3-[5-(4-Fluoro­phen­yl)-1,3,4-thia­diazol-2-yl]-2-(4-methoxy­phen­yl)-1,3-thia­zolidin-4-one

Yin, L.-H.; Wan, R.; Han, F.; Wang, B.; Wang, J.-T.

doi:10.1107/S1600536808019089

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 64| Part 7| July 2008| Page o1359

doi:10.1107/S1600536808019089

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3-[5-(4-Fluorophenyl)-1,3,4-thiadiazol-2-yl]-2-(4-methoxyphenyl)-1,3-thiazolidin-4-one

Li-He Yin,^a Rong Wan,^a ^* Feng Han,^a Bin Wang ^a and Jin-Tang Wang ^a

^aDepartment of Applied Chemistry, College of Science, Nanjing University of Technology, No. 5 Xinmofan Road, Nanjing, Nanjing 210009, People's Republic of China
^*Correspondence e-mail: rwan@njut.edu.cn

(Received 22 June 2008; accepted 24 June 2008; online 28 June 2008)

The title compound, C₁₈H₁₄FN₃O₂S₂, was synthesized by the reaction of 5-(4-fluorophenyl)-N-(4-methoxybenzylidene)-1,3,4-thiadiazol-2-amine and mercaptoacetic acid. The thiazolidinone ring adopts a twist conformation. The 4-methoxyphenyl ring is almost perpendicular to the thiadiazole ring, making a dihedral angle of 88.4 (3)°. The 4-fluorophenyl ring is nearly coplanar with the thiadiazole 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_r = 387.44
Triclinic, $[P \overline 1]$
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[F² > 2σ(F²)] = 0.070
wR(F²) = 0.186
S = 1.00
3120 reflections
229 parameters
48 restraints
H-atom parameters constrained
Δρ_max = 0.41 e Å⁻³
Δρ_min = −0.52 e Å⁻³

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) x-1, y, z.

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.

Supporting information

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

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

checkCIF report

Comment top

1,3,4-Thiadiazole derivatives containing the thiazolidinone unit are of great interest because of their chemical and pharmaceutical properties. Some derivatives have fungicidal activities and exhibit certain herbicidal activities (Chen et al., 2000; Kidwai et al., 2000; Vicentini et al., 1998). Some show insecticidal activities (Arun et al., 1999; Wasfy et al., 1996).

We report here the crystal structure of the titled compound, (I). The molecular strucutre of (I) is shown in Fig.1. In this structure, the thiazolidinone adopts a twist conformation, the dihedral angle between the C9/S1/C10 and C9/N1/C10 is 15.5 (7)°. The thiadiazole ring is an aromatic heterocyclic ring, all atoms are in the same plane. The angle between the thiadiazole ring and the 4-fluorophenyl ring is 6.8 (3)°. The 4-methoxyphenyl ring is nearly perpendicular to the thiadiazole ring, with the dihedral angle being 88.4 (3)°. There are intramolecular C—H···S and C—H···N hydrogen bonding interactions in the molecule structure. In the crystal structure, intermolecular C—H···O hydrogen bonding interactionss link the molecules (Table 1 and Fig. 2).

Related literature top

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 top

5-(4-Fluorophenyl)-N-(4-methoxybenzylidene)-1,3,4-thiadiazol -2-amine(5 mmol) and mercapto-acetic acid (5 mmol) were added in toluene (50 ml). The water was removed by distillation for 5 h. The reaction mixture was left to cool to room temperature, filtered, and the filter cake was crystallized from acetone to give pure compound (I) [m.p. 341–345 K]). Crystals of (I) suitable for X-ray diffraction were obtained by slow evaporation of an acetone solution.

Computing details top

Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CAD-4 Software (Enraf–Nonius, 1989); 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 (Sheldrick, 2008).

Figures top

	Fig. 1. A view of the molecular structure of (I). Displacement ellipsoids are drawn at the 50% probability level. Dashed lines indicate intramolecular C—H···S and C—H···N hydrogen bonding interactions.
	Fig. 2. A packing diagram for (I). Dashed lines indicate intramolecular C—H···S and C—H···N, and intermolecular C—H···O hydrogen bonding interactionss.

3-[5-(4-Fluorophenyl)-1,3,4-thiadiazol-2-yl]-2-(4-methoxyphenyl)- 1,3-thiazolidin-4-one top

Crystal data top

C₁₈H₁₄FN₃O₂S₂	Z = 2
M_r = 387.44	F(000) = 400
Triclinic, P1	D_x = 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 = 9–12°
α = 75.78 (3)°	µ = 0.34 mm⁻¹
β = 82.44 (3)°	T = 298 K
γ = 71.11 (3)°	Block, colourless
V = 869.0 (3) Å³	0.10 × 0.05 × 0.05 mm

Data collection top

Enraf–Nonius CAD-4 diffractometer	2054 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.023
Graphite monochromator	θ_max = 25.2°, θ_min = 1.3°
ω/2θ scans	h = −7→7
Absorption correction: ψ scan (North et al., 1968)	k = −10→10
T_min = 0.967, T_max = 0.984	l = 0→19
3421 measured reflections	3 standard reflections every 200 reflections
3120 independent reflections	intensity decay: none

Refinement top

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)] = 0.070	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.186	H-atom parameters constrained
S = 1.00	w = 1/[σ²(F_o²) + (0.05P)² + 2.5P] where P = (F_o² + 2F_c²)/3
3120 reflections	(Δ/σ)_max < 0.001
229 parameters	Δρ_max = 0.41 e Å⁻³
48 restraints	Δρ_min = −0.52 e Å⁻³

Crystal data top

C₁₈H₁₄FN₃O₂S₂	γ = 71.11 (3)°
M_r = 387.44	V = 869.0 (3) Å³
Triclinic, P1	Z = 2
a = 6.4550 (13) Å	Mo Kα radiation
b = 8.9200 (18) Å	µ = 0.34 mm⁻¹
c = 16.483 (3) Å	T = 298 K
α = 75.78 (3)°	0.10 × 0.05 × 0.05 mm
β = 82.44 (3)°

Data collection top

Enraf–Nonius CAD-4 diffractometer	2054 reflections with I > 2σ(I)
Absorption correction: ψ scan (North et al., 1968)	R_int = 0.023
T_min = 0.967, T_max = 0.984	3 standard reflections every 200 reflections
3421 measured reflections	intensity decay: none
3120 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.070	48 restraints
wR(F²) = 0.186	H-atom parameters constrained
S = 1.00	Δρ_max = 0.41 e Å⁻³
3120 reflections	Δρ_min = −0.52 e Å⁻³
229 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) x−1, y, z.

Experimental details

Crystal data
Chemical formula	C₁₈H₁₄FN₃O₂S₂
M_r	387.44
Crystal system, space group	Triclinic, P1
Temperature (K)	298
a, b, c (Å)	6.4550 (13), 8.9200 (18), 16.483 (3)
α, β, γ (°)	75.78 (3), 82.44 (3), 71.11 (3)
V (Å³)	869.0 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.34
Crystal size (mm)	0.10 × 0.05 × 0.05

Data collection
Diffractometer	Enraf–Nonius CAD-4 diffractometer
Absorption correction	ψ scan (North et al., 1968)
T_min, T_max	0.967, 0.984
No. of measured, independent and observed [I > 2σ(I)] reflections	3421, 3120, 2054
R_int	0.023
(sin θ/λ)_max (Å⁻¹)	0.598

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.070, 0.186, 1.00
No. of reflections	3120
No. of parameters	229
No. of restraints	48
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.41, −0.52

Computer programs: CAD-4 Software (Enraf–Nonius, 1989), XCAD4 (Harms & Wocadlo, 1995), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

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) x−1, y, z.

Acknowledgements

The authors thank Professor Hua-Qin Wang of Nanjing University for carrying out the X-ray crystallographic analysis.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19. CrossRef Web of Science Google Scholar
Arun, K. P., Nag, V. L. & Panda, C. S. (1999). Indian J. Chem. Sect. B, 38, 998–1001. Google Scholar
Chen, H. S., Li, Z. M. & Han, Y. F. (2000). J. Agric. Food Chem. 48, 5312–5315. Web of Science CrossRef PubMed CAS Google Scholar
Enraf–Nonius (1989). CAD-4 Software. Enraf–Nonius, Delft, The Netherlands. Google Scholar
Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany. Google Scholar
Kidwai, M., Negi, N. & Misra, P. (2000). J. Indian Chem. Soc. 77, 46–48. CAS Google Scholar
North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351–359. CrossRef IUCr Journals Web of Science Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Vicentini, C. B., Manfrini, M., Veronese, A. C. & Guarneri, M. (1998). J. Heterocycl. Chem. 35, 29–36. CrossRef CAS Google Scholar
Wasfy, A. A., Nassar, S. A. & Eissa, A. M. (1996). Indian J. Chem. Sect. B, 35, 1218–1220. Google Scholar

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Volume 64| Part 7| July 2008| Page o1359

doi:10.1107/S1600536808019089

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

3-[5-(4-Fluoro­phen­yl)-1,3,4-thia­diazol-2-yl]-2-(4-meth­oxy­phen­yl)-1,3-thia­zolidin-4-one

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

3-[5-(4-Fluorophenyl)-1,3,4-thiadiazol-2-yl]-2-(4-methoxyphenyl)-1,3-thiazolidin-4-one