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

In the title compound, C(16)H(18)N(2)O(2)S, the piperidine ring adopts a chair conformation. The central 4-thia-zolidinone ring makes dihedral angles of 12.01 (7) and 51.42 (9)°, respectively, with the benzene ring and the least-squares plane of the piperidine ring. An intra-molecular C-H⋯S hydrogen bond stabilizes the mol-ecular structure and generates an S(6) ring motif. In the crystal, mol-ecules are linked into a tape along the c axis by inter-molecular C-H⋯O hydrogen bonds.

Related literature

For general background to the title compound, 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 hydrogen-bond motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C16H18N2O2S

M = 302.38

Monoclinic,

a = 8.5811 (3) Å

b = 16.5165 (6) Å

c = 12.4930 (4) Å

β = 121.518 (2)°

V = 1509.42 (9) Å3

Z = 4

Mo Kα radiation

μ = 0.22 mm−1

T = 297 K

0.61 × 0.26 × 0.23 mm

Data collection

Bruker APEXII DUO CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.877, T max = 0.950

20021 measured reflections

5432 independent reflections

4148 reflections with I > 2σ(I)

R int = 0.023

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.119

S = 1.02

5432 reflections

191 parameters

H-atom parameters constrained

Δρmax = 0.31 e Å−3

Δρmin = −0.17 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/S1600536811025761/is2743sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811025761/is2743Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811025761/is2743Isup3.cml

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

C16H18N2O2S	F(000) = 640
Mr = 302.38	Dx = 1.331 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 6389 reflections
a = 8.5811 (3) Å	θ = 2.8–32.3°
b = 16.5165 (6) Å	µ = 0.22 mm−1
c = 12.4930 (4) Å	T = 297 K
β = 121.518 (2)°	Block, brown
V = 1509.42 (9) Å3	0.61 × 0.26 × 0.23 mm
Z = 4

Bruker APEXII DUO CCD area-detector diffractometer	5432 independent reflections
Radiation source: fine-focus sealed tube	4148 reflections with I > 2σ(I)
graphite	Rint = 0.023
φ and ω scans	θmax = 32.6°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −12→12
Tmin = 0.877, Tmax = 0.950	k = −25→25
20021 measured reflections	l = −17→18

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.119	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.0606P)2 + 0.2092P] where P = (Fo2 + 2Fc2)/3
5432 reflections	(Δ/σ)max = 0.001
191 parameters	Δρmax = 0.31 e Å−3
0 restraints	Δρmin = −0.17 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
S1	0.20003 (4)	0.555618 (16)	0.50684 (2)	0.03982 (9)
O1	0.39228 (18)	0.38959 (6)	0.75694 (9)	0.0638 (3)
O2	0.27412 (16)	0.35919 (6)	0.04461 (9)	0.0561 (2)
N1	0.28424 (15)	0.51913 (6)	0.73753 (9)	0.0425 (2)
N2	0.16266 (16)	0.64775 (6)	0.66938 (10)	0.0455 (2)
C1	0.32029 (16)	0.31624 (6)	0.34274 (10)	0.0382 (2)
H1A	0.3436	0.2711	0.3935	0.046*
C2	0.30857 (17)	0.30703 (7)	0.22911 (11)	0.0418 (2)
H2A	0.3216	0.2560	0.2034	0.050*
C3	0.27723 (16)	0.37401 (7)	0.15287 (11)	0.0409 (2)
C4	0.2523 (2)	0.44940 (7)	0.19023 (12)	0.0479 (3)
H4A	0.2292	0.4944	0.1392	0.057*
C5	0.2618 (2)	0.45754 (6)	0.30353 (12)	0.0457 (3)
H5A	0.2434	0.5084	0.3271	0.055*
C6	0.29786 (15)	0.39221 (6)	0.38362 (10)	0.0349 (2)
C7	0.31827 (16)	0.39806 (6)	0.50618 (10)	0.0374 (2)
H7A	0.3601	0.3509	0.5536	0.045*
C8	0.28758 (16)	0.45928 (6)	0.56330 (10)	0.0366 (2)
C9	0.32720 (18)	0.45128 (7)	0.69525 (11)	0.0422 (2)
C10	0.21678 (16)	0.57634 (6)	0.65225 (10)	0.0375 (2)
C11	0.1834 (2)	0.66894 (8)	0.79030 (12)	0.0500 (3)
H11A	0.2454	0.6255	0.8501	0.060*
H11B	0.0640	0.6764	0.7798	0.060*
C12	0.2935 (2)	0.74644 (8)	0.83907 (13)	0.0562 (3)
H12A	0.2980	0.7631	0.9151	0.067*
H12B	0.4178	0.7364	0.8601	0.067*
C13	0.2120 (2)	0.81400 (9)	0.74341 (16)	0.0675 (4)
H13A	0.2908	0.8611	0.7753	0.081*
H13B	0.0938	0.8289	0.7301	0.081*
C14	0.1894 (2)	0.78837 (8)	0.61928 (15)	0.0576 (3)
H14A	0.1271	0.8307	0.5574	0.069*
H14B	0.3088	0.7804	0.6300	0.069*
C15	0.08081 (19)	0.71084 (7)	0.57317 (12)	0.0489 (3)
H15A	−0.0437	0.7208	0.5517	0.059*
H15B	0.0770	0.6927	0.4980	0.059*
C16	0.2685 (3)	0.42727 (11)	−0.02815 (15)	0.0677 (4)
H16A	0.2886	0.4093	−0.0931	0.102*
H16B	0.3621	0.4652	0.0252	0.102*
H16C	0.1511	0.4530	−0.0654	0.102*

	U11	U22	U33	U12	U13	U23
S1	0.05518 (18)	0.03126 (13)	0.03620 (14)	0.00014 (10)	0.02609 (12)	−0.00056 (9)
O1	0.1086 (9)	0.0433 (5)	0.0527 (5)	0.0192 (5)	0.0513 (6)	0.0128 (4)
O2	0.0807 (7)	0.0558 (5)	0.0460 (5)	0.0013 (5)	0.0430 (5)	−0.0033 (4)
N1	0.0585 (6)	0.0364 (4)	0.0369 (4)	−0.0010 (4)	0.0280 (4)	−0.0027 (3)
N2	0.0620 (6)	0.0336 (4)	0.0418 (5)	0.0007 (4)	0.0276 (5)	−0.0061 (4)
C1	0.0459 (6)	0.0306 (4)	0.0402 (5)	0.0027 (4)	0.0241 (5)	0.0004 (4)
C2	0.0517 (6)	0.0348 (5)	0.0436 (5)	0.0021 (4)	0.0282 (5)	−0.0047 (4)
C3	0.0470 (6)	0.0423 (5)	0.0392 (5)	−0.0020 (4)	0.0267 (5)	−0.0038 (4)
C4	0.0711 (8)	0.0361 (5)	0.0474 (6)	0.0014 (5)	0.0386 (6)	0.0040 (4)
C5	0.0724 (8)	0.0282 (4)	0.0497 (6)	0.0004 (5)	0.0411 (6)	−0.0009 (4)
C6	0.0410 (5)	0.0307 (4)	0.0364 (5)	−0.0024 (4)	0.0226 (4)	−0.0028 (3)
C7	0.0474 (6)	0.0308 (4)	0.0376 (5)	−0.0014 (4)	0.0248 (4)	−0.0004 (4)
C8	0.0461 (5)	0.0312 (4)	0.0357 (5)	−0.0037 (4)	0.0235 (4)	−0.0020 (4)
C9	0.0594 (7)	0.0352 (5)	0.0380 (5)	0.0000 (4)	0.0297 (5)	0.0006 (4)
C10	0.0447 (5)	0.0320 (4)	0.0364 (5)	−0.0058 (4)	0.0217 (4)	−0.0065 (4)
C11	0.0590 (7)	0.0486 (6)	0.0479 (6)	−0.0020 (5)	0.0319 (6)	−0.0128 (5)
C12	0.0565 (7)	0.0517 (7)	0.0551 (7)	−0.0024 (6)	0.0254 (6)	−0.0216 (6)
C13	0.0740 (10)	0.0401 (6)	0.0770 (10)	0.0010 (6)	0.0316 (8)	−0.0188 (6)
C14	0.0613 (8)	0.0362 (5)	0.0704 (9)	−0.0002 (5)	0.0311 (7)	−0.0004 (6)
C15	0.0561 (7)	0.0361 (5)	0.0490 (6)	0.0042 (5)	0.0236 (6)	−0.0020 (5)
C16	0.0943 (12)	0.0728 (10)	0.0530 (8)	−0.0026 (9)	0.0503 (8)	0.0041 (7)

S1—C8	1.7435 (11)	C7—C8	1.3407 (15)
S1—C10	1.7790 (11)	C7—H7A	0.9300
O1—C9	1.2225 (14)	C8—C9	1.5047 (15)
O2—C3	1.3609 (14)	C11—C12	1.5166 (19)
O2—C16	1.4309 (19)	C11—H11A	0.9700
N1—C10	1.3108 (14)	C11—H11B	0.9700
N1—C9	1.3691 (15)	C12—C13	1.513 (2)
N2—C10	1.3252 (14)	C12—H12A	0.9700
N2—C15	1.4634 (16)	C12—H12B	0.9700
N2—C11	1.4680 (16)	C13—C14	1.519 (2)
C1—C2	1.3781 (16)	C13—H13A	0.9700
C1—C6	1.4053 (14)	C13—H13B	0.9700
C1—H1A	0.9300	C14—C15	1.5096 (18)
C2—C3	1.3912 (16)	C14—H14A	0.9700
C2—H2A	0.9300	C14—H14B	0.9700
C3—C4	1.3852 (16)	C15—H15A	0.9700
C4—C5	1.3811 (17)	C15—H15B	0.9700
C4—H4A	0.9300	C16—H16A	0.9600
C5—C6	1.3919 (15)	C16—H16B	0.9600
C5—H5A	0.9300	C16—H16C	0.9600
C6—C7	1.4506 (15)
C8—S1—C10	88.56 (5)	N2—C11—C12	109.25 (12)
C3—O2—C16	117.82 (11)	N2—C11—H11A	109.8
C10—N1—C9	111.72 (9)	C12—C11—H11A	109.8
C10—N2—C15	124.01 (10)	N2—C11—H11B	109.8
C10—N2—C11	120.94 (10)	C12—C11—H11B	109.8
C15—N2—C11	115.05 (10)	H11A—C11—H11B	108.3
C2—C1—C6	121.52 (10)	C13—C12—C11	111.81 (12)
C2—C1—H1A	119.2	C13—C12—H12A	109.3
C6—C1—H1A	119.2	C11—C12—H12A	109.3
C1—C2—C3	120.09 (10)	C13—C12—H12B	109.3
C1—C2—H2A	120.0	C11—C12—H12B	109.3
C3—C2—H2A	120.0	H12A—C12—H12B	107.9
O2—C3—C4	124.79 (11)	C12—C13—C14	111.12 (11)
O2—C3—C2	115.70 (10)	C12—C13—H13A	109.4
C4—C3—C2	119.52 (10)	C14—C13—H13A	109.4
C5—C4—C3	119.75 (11)	C12—C13—H13B	109.4
C5—C4—H4A	120.1	C14—C13—H13B	109.4
C3—C4—H4A	120.1	H13A—C13—H13B	108.0
C4—C5—C6	122.21 (10)	C15—C14—C13	110.46 (13)
C4—C5—H5A	118.9	C15—C14—H14A	109.6
C6—C5—H5A	118.9	C13—C14—H14A	109.6
C5—C6—C1	116.88 (10)	C15—C14—H14B	109.6
C5—C6—C7	124.46 (9)	C13—C14—H14B	109.6
C1—C6—C7	118.64 (9)	H14A—C14—H14B	108.1
C8—C7—C6	131.54 (10)	N2—C15—C14	110.80 (11)
C8—C7—H7A	114.2	N2—C15—H15A	109.5
C6—C7—H7A	114.2	C14—C15—H15A	109.5
C7—C8—C9	121.47 (10)	N2—C15—H15B	109.5
C7—C8—S1	129.49 (9)	C14—C15—H15B	109.5
C9—C8—S1	109.03 (7)	H15A—C15—H15B	108.1
O1—C9—N1	124.43 (11)	O2—C16—H16A	109.5
O1—C9—C8	122.07 (10)	O2—C16—H16B	109.5
N1—C9—C8	113.49 (9)	H16A—C16—H16B	109.5
N1—C10—N2	123.60 (10)	O2—C16—H16C	109.5
N1—C10—S1	117.18 (8)	H16A—C16—H16C	109.5
N2—C10—S1	119.22 (9)	H16B—C16—H16C	109.5
C6—C1—C2—C3	1.20 (18)	C7—C8—C9—O1	1.5 (2)
C16—O2—C3—C4	8.6 (2)	S1—C8—C9—O1	−178.96 (12)
C16—O2—C3—C2	−171.27 (13)	C7—C8—C9—N1	−178.78 (11)
C1—C2—C3—O2	177.84 (11)	S1—C8—C9—N1	0.74 (13)
C1—C2—C3—C4	−2.01 (19)	C9—N1—C10—N2	179.29 (12)
O2—C3—C4—C5	−178.76 (13)	C9—N1—C10—S1	−1.17 (14)
C2—C3—C4—C5	1.1 (2)	C15—N2—C10—N1	−177.59 (12)
C3—C4—C5—C6	0.7 (2)	C11—N2—C10—N1	2.90 (19)
C4—C5—C6—C1	−1.5 (2)	C15—N2—C10—S1	2.88 (17)
C4—C5—C6—C7	176.81 (12)	C11—N2—C10—S1	−176.63 (9)
C2—C1—C6—C5	0.53 (17)	C8—S1—C10—N1	1.37 (10)
C2—C1—C6—C7	−177.87 (11)	C8—S1—C10—N2	−179.07 (10)
C5—C6—C7—C8	9.2 (2)	C10—N2—C11—C12	123.69 (13)
C1—C6—C7—C8	−172.51 (12)	C15—N2—C11—C12	−55.87 (15)
C6—C7—C8—C9	−177.40 (11)	N2—C11—C12—C13	53.89 (16)
C6—C7—C8—S1	3.2 (2)	C11—C12—C13—C14	−54.80 (18)
C10—S1—C8—C7	178.38 (12)	C12—C13—C14—C15	54.15 (17)
C10—S1—C8—C9	−1.08 (9)	C10—N2—C15—C14	−122.75 (14)
C10—N1—C9—O1	179.94 (14)	C11—N2—C15—C14	56.79 (16)
C10—N1—C9—C8	0.25 (15)	C13—C14—C15—N2	−54.03 (16)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2A···O1i	0.93	2.48	3.3048 (16)	147
C5—H5A···S1	0.93	2.58	3.2809 (15)	132
C16—H16A···O1ii	0.96	2.48	3.421 (3)	167

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2A⋯O1i	0.93	2.48	3.3048 (16)	147
C5—H5A⋯S1	0.93	2.58	3.2809 (15)	132
C16—H16A⋯O1ii	0.96	2.48	3.421 (3)	167

Symmetry codes: (i) ; (ii) .