2-(2-Chloro-3-quinol-yl)-3-phenyl-thia-zolidin-4-one.

In the title compound, C(18)H(13)ClN(2)OS, the thia-zolidinone ring is slightly distorted and adopts a envelope conformation. The basal plane is nearly perpendicular to the quinoline ring, forming a dihedral angle of 86.1 (1)°, and makes a dihedral angle of 14.9 (1)° to the benzene ring. The benzene ring is also nearly perpendicular to the quinoline ring, forming a dihedral angle of 89.4 (1)°. In the crystal, non-classical C-H⋯O and C-H⋯N hydrogen bonds link the mol-ecules, forming polymers along b.

Related literature

For the biological activity of thia­zolidinone derivatives, see: Abd Elhafez et al. (2003 ▶); Kuecuekguezel et al. (2006 ▶); Shih & Ke (2004 ▶); Subudhi et al. (2007 ▶); Srivastava et al. (2006 ▶).

Experimental

Crystal data

C18H13ClN2OS

M = 340.81

Monoclinic,

a = 16.1192 (6) Å

b = 12.7502 (5) Å

c = 16.8949 (6) Å

β = 110.379 (2)°

V = 3255.0 (2) Å3

Z = 8

Mo Kα radiation

μ = 0.37 mm−1

T = 296 K

0.35 × 0.20 × 0.15 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: none

12810 measured reflections

2883 independent reflections

2165 reflections with I > 2σ(I)

R int = 0.027

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.098

S = 1.05

2883 reflections

208 parameters

H-atom parameters constrained

Δρmax = 0.22 e Å−3

Δρmin = −0.24 e Å−3

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); data reduction: SAINT; 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/S1600536809041543/gw2069sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809041543/gw2069Isup2.hkl

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

C18H13ClN2OS	F(000) = 1408
Mr = 340.81	Dx = 1.391 Mg m−3
Monoclinic, C2/c	Melting point = 426–428 K
Hall symbol: -C 2yc	Mo Kα radiation, λ = 0.71073 Å
a = 16.1192 (6) Å	Cell parameters from 3808 reflections
b = 12.7502 (5) Å	θ = 2.7–26.3°
c = 16.8949 (6) Å	µ = 0.37 mm−1
β = 110.379 (2)°	T = 296 K
V = 3255.0 (2) Å3	Block, pale yellow
Z = 8	0.35 × 0.20 × 0.15 mm

Bruker SMART CCD area-detector diffractometer	2165 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.027
graphite	θmax = 25.0°, θmin = 2.1°
φ and ω scans	h = −19→19
12810 measured reflections	k = −14→15
2883 independent reflections	l = −20→20

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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.098	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0404P)2 + 1.9966P] where P = (Fo2 + 2Fc2)/3
2883 reflections	(Δ/σ)max = 0.001
208 parameters	Δρmax = 0.22 e Å−3
0 restraints	Δρmin = −0.24 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	0.18759 (4)	0.86407 (6)	0.14286 (3)	0.0776 (2)
S1	0.35490 (4)	1.06043 (5)	0.23906 (4)	0.0743 (2)
N1	0.13806 (10)	0.84780 (14)	0.27204 (10)	0.0529 (4)
C5	0.23728 (14)	0.88458 (16)	0.50321 (12)	0.0505 (5)
H5A	0.2911	0.9013	0.5446	0.061*
C2	0.29190 (12)	0.89607 (15)	0.30682 (11)	0.0432 (5)
C1	0.20616 (13)	0.86948 (16)	0.25139 (11)	0.0486 (5)
N2	0.45307 (10)	0.91604 (14)	0.33821 (9)	0.0483 (4)
C9	0.14837 (12)	0.85342 (15)	0.35618 (12)	0.0455 (5)
C3	0.30220 (12)	0.89873 (15)	0.39034 (11)	0.0433 (5)
H3A	0.3576	0.9137	0.4300	0.052*
C4	0.23063 (12)	0.87924 (15)	0.41773 (11)	0.0418 (4)
C8	0.07547 (14)	0.83422 (19)	0.38073 (13)	0.0581 (6)
H8A	0.0210	0.8175	0.3403	0.070*
C10	0.36487 (12)	0.92437 (17)	0.27408 (11)	0.0488 (5)
H10A	0.3613	0.8785	0.2265	0.059*
C13	0.49430 (13)	0.81620 (18)	0.35847 (12)	0.0516 (5)
C6	0.16534 (14)	0.86545 (18)	0.52517 (13)	0.0578 (6)
H6A	0.1701	0.8693	0.5816	0.069*
C7	0.08402 (14)	0.8399 (2)	0.46357 (14)	0.0635 (6)
H7A	0.0353	0.8268	0.4795	0.076*
O1	0.55375 (11)	1.01688 (16)	0.43920 (10)	0.0849 (6)
C18	0.44621 (16)	0.72616 (19)	0.32907 (14)	0.0624 (6)
H18A	0.3863	0.7308	0.2969	0.075*
C12	0.48571 (15)	1.0079 (2)	0.37932 (14)	0.0613 (6)
C14	0.58436 (16)	0.8072 (2)	0.40572 (14)	0.0731 (7)
H14A	0.6184	0.8669	0.4258	0.088*
C11	0.42542 (19)	1.0985 (2)	0.34260 (17)	0.0841 (8)
H11A	0.4596	1.1600	0.3396	0.101*
H11B	0.3904	1.1150	0.3775	0.101*
C16	0.5747 (2)	0.6209 (3)	0.3948 (2)	0.0937 (9)
H16A	0.6015	0.5556	0.4082	0.112*
C17	0.4867 (2)	0.6282 (2)	0.34713 (18)	0.0835 (8)
H17A	0.4539	0.5677	0.3268	0.100*
C15	0.6223 (2)	0.7092 (3)	0.42233 (18)	0.0950 (10)
H15A	0.6824	0.7036	0.4534	0.114*

	U11	U22	U33	U12	U13	U23
Cl1	0.0609 (4)	0.1297 (6)	0.0347 (3)	−0.0162 (4)	0.0073 (2)	−0.0082 (3)
S1	0.0791 (5)	0.0764 (4)	0.0645 (4)	−0.0054 (4)	0.0214 (3)	0.0224 (3)
N1	0.0406 (9)	0.0694 (12)	0.0419 (9)	−0.0089 (9)	0.0060 (7)	−0.0041 (8)
C5	0.0442 (11)	0.0637 (13)	0.0414 (10)	−0.0034 (10)	0.0122 (9)	−0.0016 (10)
C2	0.0385 (10)	0.0500 (11)	0.0375 (9)	−0.0028 (9)	0.0086 (8)	−0.0009 (8)
C1	0.0451 (11)	0.0600 (13)	0.0352 (10)	−0.0032 (10)	0.0072 (9)	−0.0028 (9)
N2	0.0397 (9)	0.0629 (11)	0.0414 (8)	−0.0110 (8)	0.0131 (7)	−0.0021 (8)
C9	0.0404 (11)	0.0488 (12)	0.0443 (10)	−0.0034 (9)	0.0108 (9)	−0.0007 (9)
C3	0.0337 (10)	0.0538 (12)	0.0380 (10)	−0.0036 (9)	0.0069 (8)	−0.0020 (8)
C4	0.0379 (10)	0.0457 (11)	0.0392 (9)	−0.0010 (9)	0.0099 (8)	−0.0007 (8)
C8	0.0407 (11)	0.0739 (15)	0.0563 (13)	−0.0125 (11)	0.0128 (10)	−0.0010 (11)
C10	0.0444 (11)	0.0641 (13)	0.0360 (10)	−0.0066 (10)	0.0116 (8)	−0.0013 (9)
C13	0.0488 (12)	0.0720 (15)	0.0406 (10)	−0.0003 (11)	0.0237 (9)	0.0066 (10)
C6	0.0576 (13)	0.0723 (15)	0.0474 (11)	−0.0042 (12)	0.0233 (10)	0.0014 (10)
C7	0.0489 (13)	0.0824 (17)	0.0647 (14)	−0.0100 (12)	0.0266 (11)	0.0031 (12)
O1	0.0623 (10)	0.1135 (15)	0.0676 (10)	−0.0327 (10)	0.0083 (9)	−0.0206 (10)
C18	0.0603 (14)	0.0692 (16)	0.0676 (14)	−0.0016 (13)	0.0346 (12)	−0.0020 (12)
C12	0.0547 (13)	0.0780 (17)	0.0527 (12)	−0.0226 (13)	0.0204 (11)	−0.0058 (12)
C14	0.0569 (14)	0.099 (2)	0.0590 (14)	0.0021 (14)	0.0147 (11)	0.0118 (13)
C11	0.097 (2)	0.0620 (16)	0.0873 (18)	−0.0189 (15)	0.0247 (16)	−0.0036 (14)
C16	0.102 (3)	0.094 (2)	0.096 (2)	0.032 (2)	0.048 (2)	0.0265 (18)
C17	0.104 (2)	0.0750 (19)	0.090 (2)	0.0042 (17)	0.0571 (18)	0.0035 (15)
C15	0.0746 (19)	0.123 (3)	0.0808 (19)	0.029 (2)	0.0185 (15)	0.0279 (19)

Cl1—C1	1.7534 (19)	C10—H10A	0.9800
S1—C11	1.790 (3)	C13—C18	1.377 (3)
S1—C10	1.822 (2)	C13—C14	1.397 (3)
N1—C1	1.292 (3)	C6—C7	1.399 (3)
N1—C9	1.374 (2)	C6—H6A	0.9300
C5—C6	1.357 (3)	C7—H7A	0.9300
C5—C4	1.412 (3)	O1—C12	1.211 (3)
C5—H5A	0.9300	C18—C17	1.393 (4)
C2—C3	1.363 (2)	C18—H18A	0.9300
C2—C1	1.414 (3)	C12—C11	1.497 (4)
C2—C10	1.508 (3)	C14—C15	1.377 (4)
N2—C12	1.370 (3)	C14—H14A	0.9300
N2—C13	1.422 (3)	C11—H11A	0.9700
N2—C10	1.461 (2)	C11—H11B	0.9700
C9—C8	1.397 (3)	C16—C15	1.349 (4)
C9—C4	1.410 (2)	C16—C17	1.369 (4)
C3—C4	1.407 (3)	C16—H16A	0.9300
C3—H3A	0.9300	C17—H17A	0.9300
C8—C7	1.360 (3)	C15—H15A	0.9300
C8—H8A	0.9300
C11—S1—C10	89.23 (11)	C18—C13—N2	120.15 (19)
C1—N1—C9	117.38 (16)	C14—C13—N2	121.1 (2)
C6—C5—C4	120.21 (19)	C5—C6—C7	120.5 (2)
C6—C5—H5A	119.9	C5—C6—H6A	119.8
C4—C5—H5A	119.9	C7—C6—H6A	119.8
C3—C2—C1	115.48 (18)	C8—C7—C6	120.7 (2)
C3—C2—C10	123.01 (16)	C8—C7—H7A	119.6
C1—C2—C10	121.45 (16)	C6—C7—H7A	119.6
N1—C1—C2	126.77 (18)	C13—C18—C17	120.4 (2)
N1—C1—Cl1	114.97 (14)	C13—C18—H18A	119.8
C2—C1—Cl1	118.26 (16)	C17—C18—H18A	119.8
C12—N2—C13	125.37 (18)	O1—C12—N2	125.5 (2)
C12—N2—C10	114.62 (18)	O1—C12—C11	122.8 (2)
C13—N2—C10	119.76 (17)	N2—C12—C11	111.71 (19)
N1—C9—C8	119.12 (17)	C15—C14—C13	119.3 (3)
N1—C9—C4	121.27 (17)	C15—C14—H14A	120.3
C8—C9—C4	119.61 (18)	C13—C14—H14A	120.3
C2—C3—C4	121.21 (17)	C12—C11—S1	107.20 (18)
C2—C3—H3A	119.4	C12—C11—H11A	110.3
C4—C3—H3A	119.4	S1—C11—H11A	110.3
C3—C4—C9	117.83 (16)	C12—C11—H11B	110.3
C3—C4—C5	123.31 (17)	S1—C11—H11B	110.3
C9—C4—C5	118.86 (18)	H11A—C11—H11B	108.5
C7—C8—C9	120.12 (19)	C15—C16—C17	119.6 (3)
C7—C8—H8A	119.9	C15—C16—H16A	120.2
C9—C8—H8A	119.9	C17—C16—H16A	120.2
N2—C10—C2	113.12 (15)	C16—C17—C18	120.0 (3)
N2—C10—S1	105.26 (13)	C16—C17—H17A	120.0
C2—C10—S1	110.80 (14)	C18—C17—H17A	120.0
N2—C10—H10A	109.2	C16—C15—C14	121.9 (3)
C2—C10—H10A	109.2	C16—C15—H15A	119.1
S1—C10—H10A	109.2	C14—C15—H15A	119.1
C18—C13—C14	118.7 (2)
C9—N1—C1—C2	1.8 (3)	C3—C2—C10—S1	−96.2 (2)
C9—N1—C1—Cl1	−178.42 (15)	C1—C2—C10—S1	80.8 (2)
C3—C2—C1—N1	−0.1 (3)	C11—S1—C10—N2	−31.25 (16)
C10—C2—C1—N1	−177.3 (2)	C11—S1—C10—C2	91.36 (16)
C3—C2—C1—Cl1	−179.85 (15)	C12—N2—C13—C18	162.71 (19)
C10—C2—C1—Cl1	2.9 (3)	C10—N2—C13—C18	−11.2 (3)
C1—N1—C9—C8	177.7 (2)	C12—N2—C13—C14	−19.5 (3)
C1—N1—C9—C4	−1.6 (3)	C10—N2—C13—C14	166.56 (19)
C1—C2—C3—C4	−1.9 (3)	C4—C5—C6—C7	0.2 (3)
C10—C2—C3—C4	175.26 (18)	C9—C8—C7—C6	0.3 (4)
C2—C3—C4—C9	2.0 (3)	C5—C6—C7—C8	−0.2 (4)
C2—C3—C4—C5	−177.78 (19)	C14—C13—C18—C17	0.8 (3)
N1—C9—C4—C3	−0.2 (3)	N2—C13—C18—C17	178.56 (19)
C8—C9—C4—C3	−179.55 (19)	C13—N2—C12—O1	−0.8 (3)
N1—C9—C4—C5	179.58 (19)	C10—N2—C12—O1	173.4 (2)
C8—C9—C4—C5	0.3 (3)	C13—N2—C12—C11	−179.38 (19)
C6—C5—C4—C3	179.6 (2)	C10—N2—C12—C11	−5.2 (3)
C6—C5—C4—C9	−0.2 (3)	C18—C13—C14—C15	−0.7 (3)
N1—C9—C8—C7	−179.6 (2)	N2—C13—C14—C15	−178.5 (2)
C4—C9—C8—C7	−0.3 (3)	O1—C12—C11—S1	162.11 (19)
C12—N2—C10—C2	−94.5 (2)	N2—C12—C11—S1	−19.3 (2)
C13—N2—C10—C2	80.0 (2)	C10—S1—C11—C12	28.95 (19)
C12—N2—C10—S1	26.58 (19)	C15—C16—C17—C18	−1.7 (4)
C13—N2—C10—S1	−158.88 (14)	C13—C18—C17—C16	0.4 (4)
C3—C2—C10—N2	21.7 (3)	C17—C16—C15—C14	1.7 (5)
C1—C2—C10—N2	−161.27 (18)	C13—C14—C15—C16	−0.5 (4)

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8A···N1i	0.93	2.63	3.514 (3)	158
C3—H3A···O1ii	0.93	2.35	3.192 (2)	151

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C8—H8A⋯N1i	0.93	2.63	3.514 (3)	158
C3—H3A⋯O1ii	0.93	2.35	3.192 (2)	151

Symmetry codes: (i) ; (ii) .