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

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

doi:10.1107/S1600536808008465

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 64| Part 5| May 2008| Page o795

doi:10.1107/S1600536808008465

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

Rong Wan,^a ^* Li-He Yin,^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 210009, People's Republic of China
^*Correspondence e-mail: rwan@njut.edu.cn

(Received 27 March 2008; accepted 29 March 2008; online 4 April 2008)

In the molecule of the title compound, C₁₈H₁₃Cl₂N₃O₂S₂, the thiazolidinone ring has an envelope conformation with the S atom displaced by 0.394 (3) Å from the plane of the other ring atoms. The thiadiazole ring is oriented at a dihedral angle of 7.40 (4)° with respect to the 4-methoxyphenyl ring. Intramolecular C—H⋯S, C—H⋯N and C—H⋯Cl hydrogen bonds result in the formation of two planar and two non-planar five-membered rings. The planar five-membered rings are oriented at a dihedral angle of 6.23 (3)°. The 2,4-dichlorophenyl ring is oriented at dihedral angles of 84.21 (4) and 83.55 (3)° with respect to the thiadiazole and 4-methoxyphenyl rings, respectively. In the crystal structure, intermolecular C—H⋯O hydrogen bonds link the molecules into centrosymmetric dimers.

Related literature

For general background, see: Chen et al. (2000 ); Kidwai et al. (2000 ); Vicentini et al. (1998 ); Arun et al. (1999 ); Wasfy et al. (1996 ).

Experimental

Crystal data

C₁₈H₁₃Cl₂N₃O₂S₂
M_r = 438.33
Triclinic, $[P \overline 1]$
a = 7.1310 (14) Å
b = 8.1540 (16) Å
c = 16.671 (3) Å
α = 93.19 (3)°
β = 96.43 (3)°
γ = 105.89 (3)°
V = 922.7 (3) Å³
Z = 2
Mo Kα radiation
μ = 0.60 mm⁻¹
T = 298 (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 = 0.841, T_max = 0.943
3606 measured reflections
3315 independent reflections
2228 reflections with I > 2σ(I)
R_int = 0.084
3 standard reflections every 200 reflections intensity decay: none

Refinement

R[F² > 2σ(F²)] = 0.067
wR(F²) = 0.211
S = 1.02
3315 reflections
244 parameters
H-atom parameters constrained
Δρ_max = 0.47 e Å⁻³
Δρ_min = −0.61 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4—H4A⋯S1	0.93	2.79	3.180 (7)	106
C6—H6A⋯N1	0.93	2.55	2.856 (8)	100
C12—H12A⋯Cl2	0.98	2.63	3.063 (5)	107
C14—H14A⋯N3	0.93	2.54	2.863 (8)	101
C14—H14A⋯O1ⁱ	0.93	2.41	3.219 (7)	146
Symmetry code: (i) -x+2, -y+1, -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/S1600536808008465/hk2442sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808008465/hk2442Isup2.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). On the other hand, some of them show insecticidal activities (Arun et al., 1999; Wasfy et al., 1996). We report herein the crystal structure of the title compound, (I).

In the molecule of (I), (Fig. 1), rings A (C2-C7), B (S1/N1/N2/C8/C9) and D (C13-C18) are, of course, planar. The dihedral angles between them are A/B = 7.40 (4)°, A/D = 83.55 (3)° and B/D = 84.21 (4)°. So, rings A and B are nearly coplanar. Ring C (S2/N3/C10-C12) has envelope conformation with atom S2 displaced by 0.394 (3) Å from the plane of the other ring atoms. The intramolecular C-H···S, C-H···N and C-H···Cl hydrogen bonds (Table 1) result in the formation of two planar and two non-planar five-membered rings E (S1/C4/H4A/C5/C8), F (N1/C5/C6/H6A/C8) and G (N3/C12-C14/H14A), H (Cl2/C12/H12A/C13/C18). The dihedral angle between the planar rings E and F is E/F = 6.23 (3)°, and they are oriented with respect to the adjacent rings at dihedral angles of A/E = 3.26 (4)°, A/F = 4.55 (3)°, B/E = 5.03 (4)° and B/F = 7.27 (4)°. So, they are also nearly coplanar.

In the crystal structure, intermolecular C-H···O hydrogen bonds (Table 1) link the molecules into centrosymmetric dimers (Fig. 2), in which they may be effective in the stabilization of the structure.

Related literature top

For general background, see: Chen et al. (2000); Kidwai et al. (2000); Vicentini et al. (1998); Arun et al. (1999); Wasfy et al. (1996).

Experimental top

N-(2,4-dichlorobenzylidene)-5-(4-methoxyphenyl)-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. 507-509 K). Crystals of (I) suitable for X-ray analysis 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. The molecular structure of the title molecule, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. Hydrogen bonds are shown as dashed lines
	Fig. 2. A partial packing diagram of (I). Hydrogen bonds are shown as dashed lines.

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

Crystal data top

C₁₈H₁₃Cl₂N₃O₂S₂	Z = 2
M_r = 438.33	F(000) = 448
Triclinic, P1	D_x = 1.578 Mg m⁻³
Hall symbol: -P 1	Melting point = 507–509 K
a = 7.1310 (14) Å	Mo Kα radiation, λ = 0.71073 Å
b = 8.1540 (16) Å	Cell parameters from 25 reflections
c = 16.671 (3) Å	θ = 9–12°
α = 93.19 (3)°	µ = 0.60 mm⁻¹
β = 96.43 (3)°	T = 298 K
γ = 105.89 (3)°	Block, colorless
V = 922.7 (3) Å³	0.30 × 0.10 × 0.10 mm

Data collection top

Enraf–Nonius CAD-4 diffractometer	2228 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.084
Graphite monochromator	θ_max = 25.2°, θ_min = 1.2°
ω/2θ scans	h = 0→8
Absorption correction: ψ scan (North et al., 1968)	k = −9→9
T_min = 0.841, T_max = 0.943	l = −19→19
3606 measured reflections	3 standard reflections every 200 reflections
3315 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)] = 0.067	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.211	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.1P)² + 2P] where P = (F_o² + 2F_c²)/3
3315 reflections	(Δ/σ)_max < 0.001
244 parameters	Δρ_max = 0.47 e Å⁻³
0 restraints	Δρ_min = −0.61 e Å⁻³

Crystal data top

C₁₈H₁₃Cl₂N₃O₂S₂	γ = 105.89 (3)°
M_r = 438.33	V = 922.7 (3) Å³
Triclinic, P1	Z = 2
a = 7.1310 (14) Å	Mo Kα radiation
b = 8.1540 (16) Å	µ = 0.60 mm⁻¹
c = 16.671 (3) Å	T = 298 K
α = 93.19 (3)°	0.30 × 0.10 × 0.10 mm
β = 96.43 (3)°

Data collection top

Enraf–Nonius CAD-4 diffractometer	2228 reflections with I > 2σ(I)
Absorption correction: ψ scan (North et al., 1968)	R_int = 0.084
T_min = 0.841, T_max = 0.943	3 standard reflections every 200 reflections
3606 measured reflections	intensity decay: none
3315 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.067	0 restraints
wR(F²) = 0.211	H-atom parameters constrained
S = 1.02	Δρ_max = 0.47 e Å⁻³
3315 reflections	Δρ_min = −0.61 e Å⁻³
244 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 > 2sigma(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
Cl1	1.3375 (3)	0.6645 (2)	0.50289 (13)	0.0801 (6)
Cl2	1.1228 (2)	1.20318 (19)	0.40205 (10)	0.0606 (5)
S1	0.78625 (18)	0.7174 (2)	0.06058 (9)	0.0492 (4)
S2	0.5812 (2)	0.9562 (2)	0.33166 (11)	0.0659 (5)
O1	1.3277 (6)	0.6538 (6)	−0.2389 (2)	0.0616 (11)
O2	0.4564 (5)	0.6490 (6)	0.1380 (3)	0.0653 (12)
N1	1.1375 (6)	0.9039 (7)	0.1050 (3)	0.0535 (13)
N2	1.0345 (6)	0.9262 (7)	0.1690 (3)	0.0557 (13)
N3	0.7229 (6)	0.8433 (6)	0.2094 (3)	0.0488 (12)
C1	1.5346 (9)	0.7003 (9)	−0.2423 (4)	0.0677 (18)
H1B	1.5586	0.6672	−0.2955	0.102*
H1C	1.5962	0.6431	−0.2030	0.102*
H1D	1.5880	0.8220	−0.2306	0.102*
C2	1.2658 (8)	0.6915 (7)	−0.1674 (3)	0.0481 (13)
C3	1.0653 (8)	0.6308 (9)	−0.1639 (4)	0.0606 (17)
H3A	0.9826	0.5675	−0.2088	0.073*
C4	0.9884 (8)	0.6632 (8)	−0.0956 (4)	0.0556 (16)
H4A	0.8538	0.6203	−0.0944	0.067*
C5	1.1052 (7)	0.7578 (7)	−0.0282 (3)	0.0444 (13)
C6	1.3061 (8)	0.8127 (8)	−0.0323 (4)	0.0561 (16)
H6A	1.3900	0.8721	0.0131	0.067*
C7	1.3842 (8)	0.7822 (8)	−0.1009 (4)	0.0556 (16)
H7A	1.5189	0.8237	−0.1021	0.067*
C8	1.0288 (7)	0.8015 (7)	0.0450 (3)	0.0451 (13)
C9	0.8518 (7)	0.8390 (7)	0.1524 (3)	0.0457 (13)
C10	0.5300 (7)	0.7452 (8)	0.1973 (4)	0.0491 (14)
C11	0.4280 (9)	0.7736 (9)	0.2684 (4)	0.0670 (18)
H11A	0.4038	0.6734	0.2987	0.080*
H11B	0.3025	0.7928	0.2499	0.080*
C12	0.7992 (7)	0.9486 (7)	0.2846 (3)	0.0463 (13)
H12A	0.8693	1.0643	0.2731	0.056*
C13	0.9363 (7)	0.8774 (7)	0.3396 (3)	0.0414 (12)
C14	0.9118 (8)	0.7054 (7)	0.3390 (4)	0.0501 (14)
H14A	0.8099	0.6322	0.3033	0.060*
C15	1.0296 (8)	0.6354 (7)	0.3883 (4)	0.0518 (14)
H15A	1.0095	0.5175	0.3865	0.062*
C16	1.1798 (8)	0.7468 (8)	0.4411 (3)	0.0473 (13)
C17	1.2064 (7)	0.9194 (7)	0.4448 (3)	0.0464 (13)
H17A	1.3064	0.9927	0.4813	0.056*
C18	1.0853 (7)	0.9832 (7)	0.3946 (3)	0.0425 (12)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0617 (10)	0.0839 (13)	0.0961 (14)	0.0270 (9)	−0.0084 (9)	0.0253 (10)
Cl2	0.0494 (8)	0.0463 (8)	0.0828 (11)	0.0091 (6)	0.0096 (7)	−0.0025 (7)
S1	0.0242 (6)	0.0653 (10)	0.0511 (9)	0.0018 (6)	0.0043 (6)	0.0040 (7)
S2	0.0417 (8)	0.0898 (13)	0.0728 (11)	0.0289 (8)	0.0138 (8)	−0.0028 (9)
O1	0.044 (2)	0.072 (3)	0.058 (3)	−0.001 (2)	0.0138 (19)	−0.011 (2)
O2	0.028 (2)	0.088 (3)	0.068 (3)	−0.001 (2)	0.0030 (19)	−0.002 (3)
N1	0.028 (2)	0.076 (3)	0.051 (3)	0.004 (2)	0.011 (2)	−0.005 (2)
N2	0.030 (2)	0.075 (3)	0.054 (3)	0.002 (2)	0.008 (2)	−0.003 (3)
N3	0.026 (2)	0.072 (3)	0.049 (3)	0.012 (2)	0.012 (2)	0.007 (2)
C1	0.045 (3)	0.090 (5)	0.071 (4)	0.018 (3)	0.026 (3)	0.002 (4)
C2	0.038 (3)	0.049 (3)	0.053 (3)	0.004 (2)	0.009 (3)	0.006 (3)
C3	0.033 (3)	0.084 (5)	0.053 (4)	0.004 (3)	0.000 (3)	−0.010 (3)
C4	0.025 (3)	0.076 (4)	0.057 (4)	0.003 (3)	−0.001 (2)	−0.002 (3)
C5	0.029 (3)	0.048 (3)	0.052 (3)	0.003 (2)	0.004 (2)	0.005 (3)
C6	0.027 (3)	0.076 (4)	0.050 (3)	−0.005 (3)	0.001 (2)	−0.009 (3)
C7	0.029 (3)	0.075 (4)	0.055 (4)	0.001 (3)	0.009 (3)	0.001 (3)
C8	0.025 (2)	0.052 (3)	0.056 (3)	0.004 (2)	0.007 (2)	0.011 (3)
C9	0.030 (3)	0.056 (3)	0.052 (3)	0.012 (2)	0.007 (2)	0.011 (3)
C10	0.025 (3)	0.061 (4)	0.062 (4)	0.010 (2)	0.008 (3)	0.012 (3)
C11	0.039 (3)	0.092 (5)	0.072 (4)	0.018 (3)	0.020 (3)	0.008 (4)
C12	0.034 (3)	0.054 (3)	0.054 (3)	0.015 (2)	0.010 (2)	0.006 (3)
C13	0.028 (2)	0.048 (3)	0.049 (3)	0.011 (2)	0.011 (2)	0.000 (2)
C14	0.037 (3)	0.052 (3)	0.058 (4)	0.009 (3)	0.005 (3)	−0.003 (3)
C15	0.041 (3)	0.043 (3)	0.071 (4)	0.011 (3)	0.014 (3)	0.004 (3)
C16	0.035 (3)	0.058 (4)	0.053 (3)	0.016 (3)	0.010 (2)	0.011 (3)
C17	0.028 (3)	0.057 (4)	0.050 (3)	0.006 (2)	0.006 (2)	0.000 (3)
C18	0.034 (3)	0.042 (3)	0.054 (3)	0.010 (2)	0.019 (2)	0.003 (2)

Geometric parameters (Å, º) top

S1—C9	1.721 (6)	C4—C5	1.375 (8)
S1—C8	1.732 (5)	C4—H4A	0.9300
Cl1—C16	1.734 (6)	C5—C6	1.390 (7)
O1—C2	1.366 (7)	C5—C8	1.456 (8)
O1—C1	1.427 (7)	C6—C7	1.366 (8)
N1—C8	1.295 (7)	C6—H6A	0.9300
N1—N2	1.393 (6)	C7—H7A	0.9300
C1—H1B	0.9600	C10—C11	1.498 (8)
C1—H1C	0.9600	C11—H11A	0.9700
C1—H1D	0.9600	C11—H11B	0.9700
Cl2—C18	1.735 (5)	C12—C13	1.517 (7)
S2—C11	1.788 (7)	C12—H12A	0.9800
S2—C12	1.832 (5)	C13—C14	1.364 (8)
O2—C10	1.200 (7)	C13—C18	1.381 (7)
C2—C7	1.358 (8)	C14—C15	1.367 (8)
C2—C3	1.388 (7)	C14—H14A	0.9300
N2—C9	1.292 (7)	C15—C16	1.383 (8)
N3—C10	1.375 (7)	C15—H15A	0.9300
N3—C9	1.399 (7)	C16—C17	1.365 (8)
N3—C12	1.441 (7)	C17—C18	1.360 (8)
C3—C4	1.362 (8)	C17—H17A	0.9300
C3—H3A	0.9300

C9—S1—C8	86.0 (3)	N2—C9—S1	116.2 (4)
C2—O1—C1	117.6 (5)	N3—C9—S1	124.3 (4)
C8—N1—N2	113.1 (4)	O2—C10—N3	124.0 (5)
O1—C1—H1B	109.5	O2—C10—C11	125.4 (5)
O1—C1—H1C	109.5	N3—C10—C11	110.6 (5)
H1B—C1—H1C	109.5	C10—C11—S2	108.7 (4)
O1—C1—H1D	109.5	C10—C11—H11A	110.0
H1B—C1—H1D	109.5	S2—C11—H11A	110.0
H1C—C1—H1D	109.5	C10—C11—H11B	110.0
C11—S2—C12	92.5 (3)	S2—C11—H11B	110.0
C7—C2—O1	125.2 (5)	H11A—C11—H11B	108.3
C7—C2—C3	118.7 (5)	N3—C12—C13	112.7 (4)
O1—C2—C3	116.1 (5)	N3—C12—S2	104.8 (3)
C9—N2—N1	110.6 (5)	C13—C12—S2	111.2 (4)
C10—N3—C9	122.2 (5)	N3—C12—H12A	109.3
C10—N3—C12	119.5 (4)	C13—C12—H12A	109.3
C9—N3—C12	118.3 (4)	S2—C12—H12A	109.3
C4—C3—C2	120.7 (5)	C14—C13—C18	117.3 (5)
C4—C3—H3A	119.7	C14—C13—C12	121.2 (5)
C2—C3—H3A	119.7	C18—C13—C12	121.5 (5)
C3—C4—C5	121.5 (5)	C13—C14—C15	123.3 (5)
C3—C4—H4A	119.2	C13—C14—H14A	118.4
C5—C4—H4A	119.2	C15—C14—H14A	118.4
C4—C5—C6	116.7 (5)	C14—C15—C16	117.3 (5)
C4—C5—C8	123.5 (5)	C14—C15—H15A	121.4
C6—C5—C8	119.8 (5)	C16—C15—H15A	121.4
C7—C6—C5	122.1 (5)	C17—C16—C15	121.2 (5)
C7—C6—H6A	119.0	C17—C16—Cl1	119.7 (4)
C5—C6—H6A	119.0	C15—C16—Cl1	119.0 (5)
C2—C7—C6	120.2 (5)	C18—C17—C16	119.4 (5)
C2—C7—H7A	119.9	C18—C17—H17A	120.3
C6—C7—H7A	119.9	C16—C17—H17A	120.3
N1—C8—C5	122.9 (4)	C17—C18—C13	121.5 (5)
N1—C8—S1	114.1 (4)	C17—C18—Cl2	117.8 (4)
C5—C8—S1	123.0 (4)	C13—C18—Cl2	120.6 (4)
N2—C9—N3	119.5 (5)

C1—O1—C2—C7	5.7 (9)	C12—N3—C10—O2	−177.0 (6)
C1—O1—C2—C3	−174.3 (6)	C9—N3—C10—C11	179.2 (5)
C8—N1—N2—C9	−0.6 (7)	C12—N3—C10—C11	2.1 (7)
C7—C2—C3—C4	0.7 (10)	O2—C10—C11—S2	−169.0 (5)
O1—C2—C3—C4	−179.3 (6)	N3—C10—C11—S2	12.0 (7)
C2—C3—C4—C5	0.6 (10)	C12—S2—C11—C10	−17.2 (5)
C3—C4—C5—C6	−2.5 (9)	C10—N3—C12—C13	106.6 (5)
C3—C4—C5—C8	177.4 (6)	C9—N3—C12—C13	−70.6 (6)
C4—C5—C6—C7	3.2 (10)	C10—N3—C12—S2	−14.5 (6)
C8—C5—C6—C7	−176.8 (6)	C9—N3—C12—S2	168.3 (4)
O1—C2—C7—C6	179.9 (6)	C11—S2—C12—N3	17.6 (4)
C3—C2—C7—C6	−0.1 (10)	C11—S2—C12—C13	−104.5 (4)
C5—C6—C7—C2	−1.9 (10)	N3—C12—C13—C14	−31.0 (7)
N2—N1—C8—C5	−179.4 (5)	S2—C12—C13—C14	86.3 (6)
N2—N1—C8—S1	−0.9 (7)	N3—C12—C13—C18	151.9 (5)
C4—C5—C8—N1	−173.3 (6)	S2—C12—C13—C18	−90.8 (5)
C6—C5—C8—N1	6.6 (9)	C18—C13—C14—C15	−1.7 (8)
C4—C5—C8—S1	8.3 (8)	C12—C13—C14—C15	−178.9 (5)
C6—C5—C8—S1	−171.8 (5)	C13—C14—C15—C16	0.1 (9)
C9—S1—C8—N1	1.5 (5)	C14—C15—C16—C17	1.4 (8)
C9—S1—C8—C5	−179.9 (5)	C14—C15—C16—Cl1	−178.2 (4)
N1—N2—C9—N3	179.6 (5)	C15—C16—C17—C18	−1.3 (8)
N1—N2—C9—S1	1.8 (7)	Cl1—C16—C17—C18	178.3 (4)
C10—N3—C9—N2	−175.9 (5)	C16—C17—C18—C13	−0.3 (8)
C12—N3—C9—N2	1.1 (8)	C16—C17—C18—Cl2	179.4 (4)
C10—N3—C9—S1	1.7 (8)	C14—C13—C18—C17	1.7 (8)
C12—N3—C9—S1	178.7 (4)	C12—C13—C18—C17	179.0 (5)
C8—S1—C9—N2	−1.9 (5)	C14—C13—C18—Cl2	−178.0 (4)
C8—S1—C9—N3	−179.6 (5)	C12—C13—C18—Cl2	−0.7 (7)
C9—N3—C10—O2	0.1 (9)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4A···S1	0.93	2.79	3.180 (7)	106
C6—H6A···N1	0.93	2.55	2.856 (8)	100
C12—H12A···Cl2	0.98	2.63	3.063 (5)	107
C14—H14A···N3	0.93	2.54	2.863 (8)	101
C14—H14A···O1ⁱ	0.93	2.41	3.219 (7)	146

Symmetry code: (i) −x+2, −y+1, −z.

Experimental details

Crystal data
Chemical formula	C₁₈H₁₃Cl₂N₃O₂S₂
M_r	438.33
Crystal system, space group	Triclinic, P1
Temperature (K)	298
a, b, c (Å)	7.1310 (14), 8.1540 (16), 16.671 (3)
α, β, γ (°)	93.19 (3), 96.43 (3), 105.89 (3)
V (Å³)	922.7 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.60
Crystal size (mm)	0.30 × 0.10 × 0.10

Data collection
Diffractometer	Enraf–Nonius CAD-4 diffractometer
Absorption correction	ψ scan (North et al., 1968)
T_min, T_max	0.841, 0.943
No. of measured, independent and observed [I > 2σ(I)] reflections	3606, 3315, 2228
R_int	0.084
(sin θ/λ)_max (Å⁻¹)	0.599

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.067, 0.211, 1.02
No. of reflections	3315
No. of parameters	244
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.47, −0.61

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
C4—H4A···S1	0.93	2.79	3.180 (7)	106
C6—H6A···N1	0.93	2.55	2.856 (8)	100
C12—H12A···Cl2	0.98	2.63	3.063 (5)	107
C14—H14A···N3	0.93	2.54	2.863 (8)	101
C14—H14A···O1ⁱ	0.93	2.41	3.219 (7)	146

Symmetry code: (i) −x+2, −y+1, −z.

Acknowledgements

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

References

Arun, K. P., Nag, V. L. & Panda, C. S. (1999). Indian J. Chem. 38B, 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. 35B, 1218–1220. CAS Google Scholar

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Volume 64| Part 5| May 2008| Page o795

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

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

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

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