(5E)-5-(2,4-Dichloro-benzyl-idene)-2-(piperidin-1-yl)-1,3-thia-zol-4(5H)-one.

In the title compound, C(15)H(14)Cl(2)N(2)OS, the piperidine ring adopts a chair conformation. The dihedral angle between the thia-zolidine ring and the dichloro-benzene ring is 9.30 (4)°; this near coplanar conformation is stabilized by the formation of an intra-molecular C-H⋯S hydrogen bond, which generates an S(6) ring. In the crystal, mol-ecules are linked by C-H⋯O hydrogen bonds, forming [001] chains. Weak π-π inter-actions [centroid-centroid separation = 3.5460 (5) Å] consolidate the structure.

Related literature

For details and properties of the 4-thia­zolidinone ring system, see: Lesyk & Zimenkovsky (2004 ▶); Lesyk et al. (2007 ▶); Havrylyuk et al. (2009 ▶); Ahn et al. (2006 ▶); Park et al. (2008 ▶); Geronikaki et al. (2008 ▶); Zimenkovsky et al. (2005 ▶). For ring puckering, see: Cremer & Pople (1975 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C15H14Cl2N2OS

M = 341.24

Monoclinic,

a = 28.5303 (3) Å

b = 7.4915 (1) Å

c = 15.4789 (2) Å

β = 116.407 (1)°

V = 2963.17 (6) Å3

Z = 8

Mo Kα radiation

μ = 0.58 mm−1

T = 100 K

0.44 × 0.25 × 0.13 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.783, T max = 0.928

46944 measured reflections

6673 independent reflections

5955 reflections with I > 2σ(I)

R int = 0.024

Refinement

R[F 2 > 2σ(F 2)] = 0.026

wR(F 2) = 0.074

S = 1.03

6673 reflections

190 parameters

H-atom parameters constrained

Δρmax = 0.52 e Å−3

Δρmin = −0.19 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811040785/hb6435sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811040785/hb6435Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811040785/hb6435Isup3.cml

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

C15H14Cl2N2OS	F(000) = 1408
Mr = 341.24	Dx = 1.530 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 9844 reflections
a = 28.5303 (3) Å	θ = 2.7–35.2°
b = 7.4915 (1) Å	µ = 0.58 mm−1
c = 15.4789 (2) Å	T = 100 K
β = 116.407 (1)°	Block, brown
V = 2963.17 (6) Å3	0.44 × 0.25 × 0.13 mm
Z = 8

Bruker SMART APEXII CCD diffractometer	6673 independent reflections
Radiation source: fine-focus sealed tube	5955 reflections with I > 2σ(I)
graphite	Rint = 0.024
φ and ω scans	θmax = 35.4°, θmin = 2.7°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −45→46
Tmin = 0.783, Tmax = 0.928	k = −12→12
46944 measured reflections	l = −25→25

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)] = 0.026	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.074	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0364P)2 + 1.7424P] where P = (Fo2 + 2Fc2)/3
6673 reflections	(Δ/σ)max = 0.002
190 parameters	Δρmax = 0.52 e Å−3
0 restraints	Δρmin = −0.19 e Å−3

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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	0.430128 (8)	0.28966 (3)	0.729616 (15)	0.02400 (5)
Cl2	0.269296 (8)	0.51920 (3)	0.790208 (13)	0.02382 (5)
S1	0.176998 (7)	0.57324 (3)	0.374212 (12)	0.01596 (4)
O1	0.11470 (2)	0.76041 (9)	0.52929 (4)	0.02178 (12)
N1	0.09082 (3)	0.72148 (9)	0.36763 (5)	0.01686 (11)
N2	0.08873 (3)	0.66216 (10)	0.21783 (4)	0.01825 (12)
C1	0.28809 (3)	0.46653 (11)	0.54975 (5)	0.01796 (13)
H1A	0.2688	0.4850	0.4822	0.022*
C2	0.33866 (3)	0.40104 (11)	0.58547 (6)	0.01884 (13)
H2A	0.3540	0.3774	0.5433	0.023*
C3	0.36659 (3)	0.37051 (10)	0.68400 (6)	0.01726 (12)
C4	0.34481 (3)	0.40355 (11)	0.74672 (5)	0.01740 (12)
H4A	0.3639	0.3797	0.8138	0.021*
C5	0.29438 (3)	0.47245 (10)	0.70876 (5)	0.01601 (12)
C6	0.26411 (3)	0.50678 (10)	0.60961 (5)	0.01517 (12)
C7	0.21245 (3)	0.58738 (10)	0.57455 (5)	0.01636 (12)
H7A	0.2028	0.6221	0.6235	0.020*
C8	0.17611 (3)	0.62056 (10)	0.48355 (5)	0.01523 (12)
C9	0.12450 (3)	0.70822 (10)	0.46399 (5)	0.01629 (12)
C10	0.11223 (3)	0.66071 (10)	0.31348 (5)	0.01553 (12)
C11	0.03308 (3)	0.71217 (13)	0.16554 (6)	0.02211 (15)
H11A	0.0227	0.7796	0.2093	0.027*
H11B	0.0114	0.6027	0.1450	0.027*
C12	0.02289 (3)	0.82567 (13)	0.07750 (6)	0.02274 (15)
H12A	0.0392	0.9444	0.0988	0.027*
H12B	−0.0153	0.8434	0.0394	0.027*
C13	0.04478 (3)	0.73902 (13)	0.01359 (6)	0.02228 (15)
H13A	0.0257	0.6267	−0.0141	0.027*
H13B	0.0398	0.8202	−0.0403	0.027*
C14	0.10279 (3)	0.69973 (12)	0.07298 (6)	0.01982 (14)
H14A	0.1221	0.8133	0.0961	0.024*
H14B	0.1165	0.6393	0.0320	0.024*
C15	0.11176 (4)	0.58124 (12)	0.15908 (6)	0.02219 (15)
H15A	0.0958	0.4627	0.1359	0.027*
H15B	0.1498	0.5640	0.1991	0.027*

	U11	U22	U33	U12	U13	U23
Cl1	0.01844 (8)	0.02974 (10)	0.02435 (9)	0.00495 (7)	0.01001 (7)	0.00259 (7)
Cl2	0.01920 (9)	0.04116 (12)	0.01293 (7)	0.00453 (7)	0.00879 (6)	0.00332 (7)
S1	0.01586 (8)	0.02028 (8)	0.01193 (7)	0.00101 (6)	0.00634 (6)	−0.00006 (6)
O1	0.0210 (3)	0.0317 (3)	0.0141 (2)	0.0032 (2)	0.0092 (2)	−0.0011 (2)
N1	0.0159 (3)	0.0229 (3)	0.0124 (2)	0.0001 (2)	0.0069 (2)	0.0001 (2)
N2	0.0163 (3)	0.0272 (3)	0.0112 (2)	0.0023 (2)	0.0060 (2)	0.0005 (2)
C1	0.0199 (3)	0.0215 (3)	0.0134 (3)	0.0007 (3)	0.0083 (2)	0.0006 (2)
C2	0.0208 (3)	0.0212 (3)	0.0169 (3)	0.0014 (3)	0.0105 (3)	0.0005 (2)
C3	0.0165 (3)	0.0178 (3)	0.0180 (3)	0.0004 (2)	0.0081 (2)	0.0008 (2)
C4	0.0167 (3)	0.0204 (3)	0.0146 (3)	−0.0003 (2)	0.0064 (2)	0.0014 (2)
C5	0.0164 (3)	0.0203 (3)	0.0125 (3)	−0.0014 (2)	0.0075 (2)	0.0005 (2)
C6	0.0158 (3)	0.0175 (3)	0.0126 (3)	−0.0016 (2)	0.0066 (2)	0.0004 (2)
C7	0.0166 (3)	0.0201 (3)	0.0127 (3)	−0.0010 (2)	0.0068 (2)	0.0003 (2)
C8	0.0159 (3)	0.0178 (3)	0.0126 (3)	−0.0014 (2)	0.0068 (2)	−0.0002 (2)
C9	0.0164 (3)	0.0196 (3)	0.0133 (3)	−0.0010 (2)	0.0070 (2)	0.0001 (2)
C10	0.0150 (3)	0.0189 (3)	0.0125 (3)	−0.0008 (2)	0.0060 (2)	0.0003 (2)
C11	0.0155 (3)	0.0365 (4)	0.0139 (3)	0.0009 (3)	0.0061 (2)	0.0022 (3)
C12	0.0190 (3)	0.0339 (4)	0.0148 (3)	0.0050 (3)	0.0070 (3)	0.0033 (3)
C13	0.0230 (4)	0.0303 (4)	0.0133 (3)	0.0015 (3)	0.0078 (3)	0.0010 (3)
C14	0.0220 (3)	0.0245 (4)	0.0159 (3)	0.0008 (3)	0.0111 (3)	−0.0006 (3)
C15	0.0252 (4)	0.0291 (4)	0.0138 (3)	0.0072 (3)	0.0100 (3)	0.0015 (3)

Cl1—C3	1.7357 (8)	C6—C7	1.4560 (11)
Cl2—C5	1.7397 (7)	C7—C8	1.3498 (10)
S1—C8	1.7402 (7)	C7—H7A	0.9500
S1—C10	1.7839 (8)	C8—C9	1.5148 (11)
O1—C9	1.2265 (9)	C11—C12	1.5207 (12)
N1—C10	1.3186 (10)	C11—H11A	0.9900
N1—C9	1.3722 (10)	C11—H11B	0.9900
N2—C10	1.3261 (9)	C12—C13	1.5296 (12)
N2—C15	1.4690 (10)	C12—H12A	0.9900
N2—C11	1.4743 (11)	C12—H12B	0.9900
C1—C2	1.3851 (11)	C13—C14	1.5223 (12)
C1—C6	1.4075 (10)	C13—H13A	0.9900
C1—H1A	0.9500	C13—H13B	0.9900
C2—C3	1.3900 (11)	C14—C15	1.5252 (12)
C2—H2A	0.9500	C14—H14A	0.9900
C3—C4	1.3880 (11)	C14—H14B	0.9900
C4—C5	1.3893 (11)	C15—H15A	0.9900
C4—H4A	0.9500	C15—H15B	0.9900
C5—C6	1.4102 (10)
C8—S1—C10	88.74 (3)	N1—C10—S1	117.13 (5)
C10—N1—C9	111.56 (6)	N2—C10—S1	118.84 (6)
C10—N2—C15	122.99 (7)	N2—C11—C12	111.35 (7)
C10—N2—C11	120.09 (6)	N2—C11—H11A	109.4
C15—N2—C11	115.73 (6)	C12—C11—H11A	109.4
C2—C1—C6	122.55 (7)	N2—C11—H11B	109.4
C2—C1—H1A	118.7	C12—C11—H11B	109.4
C6—C1—H1A	118.7	H11A—C11—H11B	108.0
C1—C2—C3	118.91 (7)	C11—C12—C13	111.84 (7)
C1—C2—H2A	120.5	C11—C12—H12A	109.2
C3—C2—H2A	120.5	C13—C12—H12A	109.2
C4—C3—C2	121.44 (7)	C11—C12—H12B	109.2
C4—C3—Cl1	119.28 (6)	C13—C12—H12B	109.2
C2—C3—Cl1	119.29 (6)	H12A—C12—H12B	107.9
C3—C4—C5	118.17 (7)	C14—C13—C12	109.79 (6)
C3—C4—H4A	120.9	C14—C13—H13A	109.7
C5—C4—H4A	120.9	C12—C13—H13A	109.7
C4—C5—C6	123.08 (7)	C14—C13—H13B	109.7
C4—C5—Cl2	116.79 (5)	C12—C13—H13B	109.7
C6—C5—Cl2	120.12 (6)	H13A—C13—H13B	108.2
C1—C6—C5	115.83 (7)	C13—C14—C15	110.80 (7)
C1—C6—C7	123.46 (7)	C13—C14—H14A	109.5
C5—C6—C7	120.64 (7)	C15—C14—H14A	109.5
C8—C7—C6	130.21 (7)	C13—C14—H14B	109.5
C8—C7—H7A	114.9	C15—C14—H14B	109.5
C6—C7—H7A	114.9	H14A—C14—H14B	108.1
C7—C8—C9	121.03 (7)	N2—C15—C14	110.69 (7)
C7—C8—S1	129.85 (6)	N2—C15—H15A	109.5
C9—C8—S1	109.10 (5)	C14—C15—H15A	109.5
O1—C9—N1	124.51 (7)	N2—C15—H15B	109.5
O1—C9—C8	122.08 (7)	C14—C15—H15B	109.5
N1—C9—C8	113.41 (6)	H15A—C15—H15B	108.1
N1—C10—N2	124.03 (7)
C6—C1—C2—C3	1.25 (12)	C7—C8—C9—O1	3.74 (12)
C1—C2—C3—C4	0.26 (12)	S1—C8—C9—O1	−177.51 (7)
C1—C2—C3—Cl1	−179.63 (6)	C7—C8—C9—N1	−175.99 (7)
C2—C3—C4—C5	−1.49 (12)	S1—C8—C9—N1	2.77 (8)
Cl1—C3—C4—C5	178.41 (6)	C9—N1—C10—N2	−178.19 (8)
C3—C4—C5—C6	1.30 (12)	C9—N1—C10—S1	1.36 (9)
C3—C4—C5—Cl2	−177.86 (6)	C15—N2—C10—N1	−175.15 (8)
C2—C1—C6—C5	−1.41 (12)	C11—N2—C10—N1	−8.17 (12)
C2—C1—C6—C7	175.53 (8)	C15—N2—C10—S1	5.31 (11)
C4—C5—C6—C1	0.10 (11)	C11—N2—C10—S1	172.29 (6)
Cl2—C5—C6—C1	179.24 (6)	C8—S1—C10—N1	0.25 (7)
C4—C5—C6—C7	−176.93 (7)	C8—S1—C10—N2	179.82 (7)
Cl2—C5—C6—C7	2.21 (10)	C10—N2—C11—C12	140.61 (8)
C1—C6—C7—C8	7.99 (13)	C15—N2—C11—C12	−51.50 (10)
C5—C6—C7—C8	−175.21 (8)	N2—C11—C12—C13	51.51 (10)
C6—C7—C8—C9	−179.51 (7)	C11—C12—C13—C14	−55.21 (10)
C6—C7—C8—S1	2.03 (13)	C12—C13—C14—C15	56.91 (10)
C10—S1—C8—C7	177.01 (8)	C10—N2—C15—C14	−139.08 (8)
C10—S1—C8—C9	−1.60 (5)	C11—N2—C15—C14	53.41 (10)
C10—N1—C9—O1	177.67 (8)	C13—C14—C15—N2	−55.37 (9)
C10—N1—C9—C8	−2.61 (9)

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1A···S1	0.95	2.49	3.2260 (8)	134
C4—H4A···O1i	0.95	2.40	3.3080 (9)	160
C15—H15A···O1ii	0.99	2.57	3.2778 (11)	129

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1A⋯S1	0.95	2.49	3.2260 (8)	134
C4—H4A⋯O1i	0.95	2.40	3.3080 (9)	160
C15—H15A⋯O1ii	0.99	2.57	3.2778 (11)	129

Symmetry codes: (i) ; (ii) .