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

The title compound, C(19)H(15)Cl(2)N(3)OS(2), was synthesized by the reaction of N-(2,4-dichloro-phen-yl)-5-(3,5-dimethyl-phen-yl)-1,3,4-thia-diazol-2-amine and mercaptoacetic acid. The thia-zolidinone ring adopts a twist conformation. The 2,4-dichloro-phenyl ring is almost perpendicular to the thia-diazole ring, the dihedral angle being 82.8 (2)°. The 3,5-dimethyl-phenyl ring is nearly coplanar with the thia-diazole ring, the dihedral angle being 2.7 (2)°. An intramolecular C-H⋯N hydrogen bond is present.

Related literature

For general background, see: Arun et al. (1999 ▶); Chen et al. (2000 ▶); Kidwai et al. (2000 ▶); Vicentini et al. (1998 ▶); Wasfy et al. (1996 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C19H15Cl2N3OS2

M = 436.36

Triclinic,

a = 8.1760 (16) Å

b = 9.1650 (18) Å

c = 14.483 (3) Å

α = 80.60 (3)°

β = 80.82 (3)°

γ = 63.92 (3)°

V = 956.9 (4) Å3

Z = 2

Mo Kα radiation

μ = 0.57 mm−1

T = 298 (2) K

0.40 × 0.30 × 0.20 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

Absorption correction: ψ scan (North et al., 1968 ▶) T min = 0.803, T max = 0.894

4042 measured reflections

3761 independent reflections

2824 reflections with I > 2σ(I)

R int = 0.044

3 standard reflections every 200 reflections intensity decay: none

Refinement

R[F 2 > 2σ(F 2)] = 0.055

wR(F 2) = 0.165

S = 1.03

3761 reflections

244 parameters

H-atom parameters constrained

Δρmax = 0.42 e Å−3

Δρmin = −0.45 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, 1997 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997 ▶); molecular graphics: SHELXTL (Siemens, 1996 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536807066068/rn2029sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807066068/rn2029Isup2.hkl

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

C19H15Cl2N3OS2	Z = 2
Mr = 436.36	F(000) = 448
Triclinic, P1	Dx = 1.514 Mg m−3
Hall symbol: -P 1	Melting point = 476–477 K
a = 8.1760 (16) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.1650 (18) Å	Cell parameters from 25 reflections
c = 14.483 (3) Å	θ = 10–14°
α = 80.60 (3)°	µ = 0.57 mm−1
β = 80.82 (3)°	T = 298 K
γ = 63.92 (3)°	Block, light yellow
V = 956.9 (4) Å3	0.40 × 0.30 × 0.20 mm

Enraf–Nonius CAD-4 diffractometer	2824 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.044
graphite	θmax = 26.0°, θmin = 1.4°
ω/2θ scans	h = −9→10
Absorption correction: ψ scan (North et al., 1968)	k = −11→11
Tmin = 0.803, Tmax = 0.894	l = 0→17
4042 measured reflections	3 standard reflections every 200 reflections
3761 independent reflections	intensity decay: none

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)] = 0.055	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.165	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.05P)2 + 2.5P] where P = (Fo2 + 2Fc2)/3
3761 reflections	(Δ/σ)max < 0.001
244 parameters	Δρmax = 0.42 e Å−3
0 restraints	Δρmin = −0.45 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
Cl1	0.6127 (2)	0.7754 (2)	−0.14356 (11)	0.0843 (5)
Cl2	1.25961 (17)	0.62298 (16)	−0.02409 (9)	0.0667 (4)
S1	1.13265 (18)	0.90179 (17)	0.12924 (9)	0.0626 (4)
S2	0.80372 (16)	0.67126 (13)	0.42066 (7)	0.0469 (3)
O	0.7989 (6)	0.9660 (4)	0.3520 (3)	0.0818 (12)
N1	0.9137 (5)	0.4033 (4)	0.3485 (2)	0.0522 (9)
N2	0.9641 (5)	0.5066 (4)	0.2796 (2)	0.0523 (9)
N3	0.9527 (5)	0.7697 (4)	0.2528 (2)	0.0487 (8)
C1	0.7096 (8)	−0.0041 (6)	0.5859 (4)	0.0672 (13)
H1B	0.6622	−0.0377	0.6465	0.101*
H1C	0.8348	−0.0796	0.5727	0.101*
H1D	0.6386	−0.0023	0.5386	0.101*
C2	0.6989 (6)	0.1640 (6)	0.5861 (3)	0.0514 (11)
C3	0.7698 (6)	0.2378 (5)	0.5073 (3)	0.0469 (10)
H3A	0.8261	0.1815	0.4547	0.056*
C4	0.7565 (6)	0.3936 (5)	0.5074 (3)	0.0439 (9)
C5	0.6693 (6)	0.4783 (6)	0.5844 (3)	0.0496 (10)
H5A	0.6602	0.5831	0.5842	0.059*
C6	0.5944 (6)	0.4091 (6)	0.6629 (3)	0.0486 (10)
C7	0.6134 (6)	0.2527 (6)	0.6616 (3)	0.0527 (11)
H7A	0.5664	0.2048	0.7140	0.063*
C8	0.4899 (7)	0.5073 (7)	0.7442 (3)	0.0698 (14)
H8A	0.4485	0.4418	0.7920	0.105*
H8B	0.3863	0.6025	0.7226	0.105*
H8C	0.5683	0.5402	0.7698	0.105*
C9	0.8307 (5)	0.4717 (5)	0.4236 (3)	0.0409 (9)
C10	0.9149 (6)	0.6481 (5)	0.3094 (3)	0.0443 (9)
C11	1.0540 (6)	0.7385 (5)	0.1604 (3)	0.0480 (10)
H11A	1.1602	0.6323	0.1651	0.058*
C12	0.9563 (9)	1.0308 (7)	0.2078 (4)	0.0745 (16)
H12A	1.0026	1.0901	0.2380	0.089*
H12B	0.8546	1.1093	0.1738	0.089*
C13	0.8942 (7)	0.9217 (6)	0.2809 (3)	0.0576 (12)
C14	0.9401 (6)	0.7419 (5)	0.0871 (3)	0.0431 (9)
C15	0.7515 (6)	0.7987 (5)	0.1026 (3)	0.0500 (10)
H15A	0.6923	0.8314	0.1610	0.060*
C16	0.6505 (6)	0.8074 (6)	0.0324 (3)	0.0532 (11)
H16A	0.5239	0.8462	0.0431	0.064*
C17	0.7404 (7)	0.7576 (5)	−0.0542 (3)	0.0538 (11)
C18	0.9264 (6)	0.6968 (5)	−0.0713 (3)	0.0505 (10)
H18A	0.9855	0.6604	−0.1290	0.061*
C19	1.0239 (6)	0.6911 (5)	−0.0003 (3)	0.0461 (10)

	U11	U22	U33	U12	U13	U23
Cl1	0.1062 (12)	0.1000 (11)	0.0749 (9)	−0.0627 (10)	−0.0278 (8)	−0.0105 (8)
Cl2	0.0586 (7)	0.0700 (8)	0.0645 (8)	−0.0285 (6)	0.0135 (6)	−0.0046 (6)
S1	0.0718 (8)	0.0738 (8)	0.0616 (7)	−0.0531 (7)	−0.0053 (6)	0.0051 (6)
S2	0.0603 (7)	0.0507 (6)	0.0407 (5)	−0.0345 (5)	−0.0035 (5)	−0.0034 (4)
O	0.130 (3)	0.067 (2)	0.062 (2)	−0.061 (2)	0.020 (2)	−0.0169 (18)
N1	0.071 (2)	0.051 (2)	0.0410 (19)	−0.0354 (19)	0.0016 (17)	0.0019 (16)
N2	0.064 (2)	0.050 (2)	0.046 (2)	−0.0316 (18)	0.0043 (17)	−0.0019 (16)
N3	0.060 (2)	0.049 (2)	0.0456 (19)	−0.0339 (18)	−0.0029 (16)	−0.0006 (16)
C1	0.079 (3)	0.058 (3)	0.066 (3)	−0.037 (3)	0.006 (3)	0.000 (2)
C2	0.063 (3)	0.065 (3)	0.041 (2)	−0.042 (2)	−0.007 (2)	0.003 (2)
C3	0.056 (2)	0.055 (2)	0.037 (2)	−0.032 (2)	0.0002 (18)	−0.0044 (18)
C4	0.048 (2)	0.053 (2)	0.041 (2)	−0.0301 (19)	−0.0090 (17)	0.0004 (18)
C5	0.057 (3)	0.059 (3)	0.047 (2)	−0.035 (2)	−0.0089 (19)	−0.006 (2)
C6	0.046 (2)	0.070 (3)	0.039 (2)	−0.032 (2)	−0.0046 (17)	−0.009 (2)
C7	0.061 (3)	0.078 (3)	0.038 (2)	−0.049 (2)	−0.0068 (19)	0.005 (2)
C8	0.075 (3)	0.095 (4)	0.056 (3)	−0.049 (3)	0.009 (2)	−0.028 (3)
C9	0.039 (2)	0.048 (2)	0.040 (2)	−0.0232 (18)	−0.0042 (16)	−0.0029 (17)
C10	0.058 (2)	0.052 (2)	0.034 (2)	−0.035 (2)	−0.0088 (17)	0.0044 (17)
C11	0.053 (2)	0.053 (2)	0.043 (2)	−0.031 (2)	0.0003 (18)	0.0011 (18)
C12	0.114 (5)	0.069 (3)	0.062 (3)	−0.064 (3)	−0.001 (3)	0.002 (3)
C13	0.080 (3)	0.052 (3)	0.053 (3)	−0.043 (2)	−0.001 (2)	0.000 (2)
C14	0.051 (2)	0.040 (2)	0.042 (2)	−0.0264 (18)	−0.0002 (18)	0.0020 (17)
C15	0.056 (3)	0.059 (3)	0.043 (2)	−0.035 (2)	−0.0004 (19)	−0.0006 (19)
C16	0.046 (2)	0.058 (3)	0.059 (3)	−0.027 (2)	−0.002 (2)	−0.004 (2)
C17	0.075 (3)	0.052 (3)	0.053 (3)	−0.043 (2)	−0.007 (2)	−0.004 (2)
C18	0.071 (3)	0.040 (2)	0.048 (2)	−0.033 (2)	0.005 (2)	−0.0052 (18)
C19	0.055 (2)	0.040 (2)	0.047 (2)	−0.0287 (19)	0.0016 (19)	0.0013 (17)

Cl1—C17	1.734 (5)	C5—C6	1.398 (6)
Cl2—C19	1.739 (4)	C5—H5A	0.9300
S1—C12	1.786 (6)	C6—C7	1.375 (6)
S1—C11	1.841 (4)	C6—C8	1.509 (6)
S2—C10	1.716 (4)	C7—H7A	0.9300
S2—C9	1.738 (4)	C8—H8A	0.9600
O—C13	1.198 (6)	C8—H8B	0.9600
N1—C9	1.285 (5)	C8—H8C	0.9600
N1—N2	1.401 (5)	C11—C14	1.507 (6)
N2—C10	1.303 (5)	C11—H11A	0.9800
N3—C13	1.368 (6)	C12—C13	1.518 (6)
N3—C10	1.391 (5)	C12—H12A	0.9700
N3—C11	1.458 (5)	C12—H12B	0.9700
C1—C2	1.504 (6)	C14—C15	1.386 (6)
C1—H1B	0.9600	C14—C19	1.388 (6)
C1—H1C	0.9600	C15—C16	1.380 (6)
C1—H1D	0.9600	C15—H15A	0.9300
C2—C7	1.376 (6)	C16—C17	1.385 (6)
C2—C3	1.406 (6)	C16—H16A	0.9300
C3—C4	1.383 (6)	C17—C18	1.365 (6)
C3—H3A	0.9300	C18—C19	1.378 (6)
C4—C5	1.378 (6)	C18—H18A	0.9300
C4—C9	1.488 (5)
C12—S1—C11	92.2 (2)	N1—C9—S2	114.6 (3)
C10—S2—C9	86.20 (19)	C4—C9—S2	120.6 (3)
C9—N1—N2	112.7 (3)	N2—C10—N3	120.8 (4)
C10—N2—N1	110.8 (3)	N2—C10—S2	115.7 (3)
C13—N3—C10	121.6 (4)	N3—C10—S2	123.5 (3)
C13—N3—C11	118.1 (3)	N3—C11—C14	113.4 (3)
C10—N3—C11	120.2 (3)	N3—C11—S1	104.4 (3)
C2—C1—H1B	109.5	C14—C11—S1	110.7 (3)
C2—C1—H1C	109.5	N3—C11—H11A	109.4
H1B—C1—H1C	109.5	C14—C11—H11A	109.4
C2—C1—H1D	109.5	S1—C11—H11A	109.4
H1B—C1—H1D	109.5	C13—C12—S1	107.3 (4)
H1C—C1—H1D	109.5	C13—C12—H12A	110.3
C7—C2—C3	117.9 (4)	S1—C12—H12A	110.3
C7—C2—C1	121.2 (4)	C13—C12—H12B	110.3
C3—C2—C1	120.9 (4)	S1—C12—H12B	110.3
C4—C3—C2	120.5 (4)	H12A—C12—H12B	108.5
C4—C3—H3A	119.8	O—C13—N3	124.4 (4)
C2—C3—H3A	119.8	O—C13—C12	124.1 (4)
C5—C4—C3	119.7 (4)	N3—C13—C12	111.5 (4)
C5—C4—C9	120.0 (4)	C15—C14—C19	117.8 (4)
C3—C4—C9	120.3 (4)	C15—C14—C11	122.4 (4)
C4—C5—C6	121.0 (4)	C19—C14—C11	119.7 (4)
C4—C5—H5A	119.5	C16—C15—C14	120.9 (4)
C6—C5—H5A	119.5	C16—C15—H15A	119.6
C7—C6—C5	117.9 (4)	C14—C15—H15A	119.6
C7—C6—C8	121.8 (4)	C15—C16—C17	119.0 (4)
C5—C6—C8	120.2 (4)	C15—C16—H16A	120.5
C6—C7—C2	123.0 (4)	C17—C16—H16A	120.5
C6—C7—H7A	118.5	C18—C17—C16	121.8 (4)
C2—C7—H7A	118.5	C18—C17—Cl1	119.2 (4)
C6—C8—H8A	109.5	C16—C17—Cl1	119.0 (4)
C6—C8—H8B	109.5	C17—C18—C19	118.0 (4)
H8A—C8—H8B	109.5	C17—C18—H18A	121.0
C6—C8—H8C	109.5	C19—C18—H18A	121.0
H8A—C8—H8C	109.5	C18—C19—C14	122.4 (4)
H8B—C8—H8C	109.5	C18—C19—Cl2	117.9 (3)
N1—C9—C4	124.8 (4)	C14—C19—Cl2	119.6 (3)
C9—N1—N2—C10	0.5 (5)	C10—N3—C11—C14	76.7 (5)
C7—C2—C3—C4	1.3 (6)	C13—N3—C11—S1	18.4 (5)
C1—C2—C3—C4	178.9 (4)	C10—N3—C11—S1	−162.7 (3)
C2—C3—C4—C5	−1.5 (6)	C12—S1—C11—N3	−22.7 (3)
C2—C3—C4—C9	−179.6 (4)	C12—S1—C11—C14	99.6 (3)
C3—C4—C5—C6	0.2 (6)	C11—S1—C12—C13	22.1 (4)
C9—C4—C5—C6	178.4 (4)	C10—N3—C13—O	−4.5 (8)
C4—C5—C6—C7	1.2 (6)	C11—N3—C13—O	174.4 (5)
C4—C5—C6—C8	−176.4 (4)	C10—N3—C13—C12	178.8 (4)
C5—C6—C7—C2	−1.4 (7)	C11—N3—C13—C12	−2.4 (6)
C8—C6—C7—C2	176.2 (4)	S1—C12—C13—O	167.6 (5)
C3—C2—C7—C6	0.2 (7)	S1—C12—C13—N3	−15.6 (6)
C1—C2—C7—C6	−177.4 (4)	N3—C11—C14—C15	11.2 (6)
N2—N1—C9—C4	178.1 (4)	S1—C11—C14—C15	−105.7 (4)
N2—N1—C9—S2	−0.3 (5)	N3—C11—C14—C19	−170.7 (3)
C5—C4—C9—N1	−179.9 (4)	S1—C11—C14—C19	72.4 (4)
C3—C4—C9—N1	−1.8 (6)	C19—C14—C15—C16	−1.3 (6)
C5—C4—C9—S2	−1.6 (5)	C11—C14—C15—C16	176.9 (4)
C3—C4—C9—S2	176.5 (3)	C14—C15—C16—C17	0.3 (7)
C10—S2—C9—N1	0.0 (3)	C15—C16—C17—C18	1.4 (7)
C10—S2—C9—C4	−178.5 (3)	C15—C16—C17—Cl1	−177.7 (3)
N1—N2—C10—N3	179.3 (4)	C16—C17—C18—C19	−2.1 (6)
N1—N2—C10—S2	−0.5 (5)	Cl1—C17—C18—C19	177.1 (3)
C13—N3—C10—N2	176.7 (4)	C17—C18—C19—C14	1.1 (6)
C11—N3—C10—N2	−2.2 (6)	C17—C18—C19—Cl2	−176.9 (3)
C13—N3—C10—S2	−3.5 (6)	C15—C14—C19—C18	0.6 (6)
C11—N3—C10—S2	177.7 (3)	C11—C14—C19—C18	−177.6 (4)
C9—S2—C10—N2	0.3 (3)	C15—C14—C19—Cl2	178.6 (3)
C9—S2—C10—N3	−179.6 (4)	C11—C14—C19—Cl2	0.4 (5)
C13—N3—C11—C14	−102.2 (4)

D—H···A	D—H	H···A	D···A	D—H···A
C15—H15A···N3	0.93	2.49	2.842 (6)	102

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C15—H15A⋯N3	0.93	2.49	2.842 (6)	102