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

In the mol-ecule of the title compound, C(18)H(13)Cl(2)N(3)O(2)S(2), the thia-zolidinone ring has an envelope conformation with the S atom displaced by 0.394 (3) Å from the plane of the other ring atoms. The thia-diazole ring is oriented at a dihedral angle of 7.40 (4)° with respect to the 4-methoxy-phenyl ring. Intra-molecular 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-dichloro-phenyl ring is oriented at dihedral angles of 84.21 (4) and 83.55 (3)° with respect to the thia-diazole and 4-methoxy-phenyl rings, respectively. In the crystal structure, inter-molecular C-H⋯O hydrogen bonds link the mol-ecules 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 = 438.33

Triclinic,

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[F 2 > 2σ(F 2)] = 0.067

wR(F 2) = 0.211

S = 1.02

3315 reflections

244 parameters

H-atom parameters constrained

Δρmax = 0.47 e Å−3

Δρmin = −0.61 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/S1600536808008465/hk2442sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808008465/hk2442Isup2.hkl

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

C18H13Cl2N3O2S2	Z = 2
Mr = 438.33	F000 = 448
Triclinic, P1	Dx = 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 = 9–12º
α = 93.19 (3)º	µ = 0.60 mm−1
β = 96.43 (3)º	T = 298 (2) K
γ = 105.89 (3)º	Block, colorless
V = 922.7 (3) Å3	0.30 × 0.10 × 0.10 mm

Enraf–Nonius CAD-4 diffractometer	Rint = 0.084
Radiation source: fine-focus sealed tube	θmax = 25.2º
Monochromator: graphite	θmin = 1.2º
T = 298(2) K	h = 0→8
ω/2θ scans	k = −9→9
Absorption correction: ψ scan(North et al., 1968)	l = −19→19
Tmin = 0.841, Tmax = 0.943	3 standard reflections
3606 measured reflections	every 200 reflections
3315 independent reflections	intensity decay: none
2228 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)] = 0.067	H-atom parameters constrained
wR(F2) = 0.211	w = 1/[σ2(Fo2) + (0.1P)2 + 2P] where P = (Fo2 + 2Fc2)/3
S = 1.02	(Δ/σ)max < 0.001
3315 reflections	Δρmax = 0.47 e Å−3
244 parameters	Δρmin = −0.61 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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.

	x	y	z	Uiso*/Ueq
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)

	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)

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)

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

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) .