(5E)-5-(4-Meth­oxy­benzyl­idene)-2-(piperidin-1-yl)-1,3-thia­zol-4(5H)-one

Fun, H.-K.; Yeap, C.S.; Lobo, P.L.; Prasad, D.J.; Poojary, B.

doi:10.1107/S1600536811025761

organic compounds

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ISSN: 2056-9890

Volume 67| Part 8| August 2011| Page o1915

doi:10.1107/S1600536811025761

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(5E)-5-(4-Methoxybenzylidene)-2-(piperidin-1-yl)-1,3-thiazol-4(5H)-one

Hoong-Kun Fun,^a ^*‡ Chin Sing Yeap,^a § Prajwal L. Lobo,^b D. Jagadeesh Prasad ^b and Boja Poojary ^b

^aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and ^bDepartment of Chemistry, Mangalore University, Karnataka, India
^*Correspondence e-mail: hkfun@usm.my

(Received 27 June 2011; accepted 29 June 2011; online 6 July 2011)

In the title compound, C₁₆H₁₈N₂O₂S, the piperidine ring adopts a chair conformation. The central 4-thiazolidinone 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 intramolecular C—H⋯S hydrogen bond stabilizes the molecular structure and generates an S(6) ring motif. In the crystal, molecules are linked into a tape along the c axis by intermolecular 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_r = 302.38
Monoclinic, P 2₁ /c
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[F² > 2σ(F²)] = 0.039
wR(F²) = 0.119
S = 1.02
5432 reflections
191 parameters
H-atom parameters constrained
Δρ_max = 0.31 e Å⁻³
Δρ_min = −0.17 e Å⁻³

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) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (ii) x, y, z-1.

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 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811025761/is2743sup1.cif

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

Supporting information file. DOI: 10.1107/S1600536811025761/is2743Isup3.cml

checkCIF report

Comment top

4-Thiazolidinone ring system is a core structure in various synthetic compounds which display a broad spectrum of biological activities (Lesyk & Zimenkovsky, 2004) including an anticancer effect (Lesyk et al., 2007; Havrylyuk et al., 2009). Mechanisms of 4-thiazolidinones and related heterocycles antitumor activity may be associated with the affinity to anticancer bio-targets, such as phosphatase of a regenerating liver (PRL-3) (Ahn et al., 2006; Park et al., 2008) and non-membrane protein tyrosine phosphatase (SHP-2) (Geronikaki et al., 2008). 5-Arylidene derivatives were previously shown as the most active group of compounds with the anticancer activity among a large pool of 4-azolidone derivatives and analogs (Zimenkovsky et al., 2005). This prompted us to synthesize title compound (I).

The central 4-thiazolidinone ring makes dihedral angles of 12.01 (7) and 51.42 (9)°, respectively, with the benzene ring and the least-squares plane of piperidine ring. The piperidine ring adopts a chair conformation. An intramolecular C5—H5A···S1 hydrogen bond (Table 1) stabilizes the molecular structure and generates an S(6) ring motif (Fig. 1; Bernstein et al., 1995). In the crystal structure, the molecules are linked into a tape along the c axis by intermolecular C16—H16A···O1 and C2—H2A···O1 hydrogen bonds (Table 1 and Fig. 2).

Related literature top

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 top

An equimolar mixture of 2-(piperidin-1-yl)-1,3-thiazol-4(5H)-one, anisaldehyde and sodium acetate in acetic acid was refluxed for 2 hrs. The product formed was filtered, washed, dried and re-crystallized from ethanol.

Computing details top

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

Figures top

	Fig. 1. The molecular structure of the title compound, with atom labels and 30% probability ellipsoids for non-H atoms. Hydrogen bonds (dashed lines) are shown.
	Fig. 2. The crystal packing of the title compound, showing the molecules linked along the c axis. Hydrogen bonds (dashed lines) are shown.

(5E)-5-(4-Methoxybenzylidene)-2-(piperidin-1-yl)-1,3-thiazol- 4(5H)-one top

Crystal data top

C₁₆H₁₈N₂O₂S	F(000) = 640
M_r = 302.38	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.0606P)² + 0.2092P] where P = (F_o² + 2F_c²)/3
5432 reflections	(Δ/σ)_max = 0.001
191 parameters	Δρ_max = 0.31 e Å⁻³
0 restraints	Δρ_min = −0.17 e Å⁻³

Crystal data top

C₁₆H₁₈N₂O₂S	V = 1509.42 (9) Å³
M_r = 302.38	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 8.5811 (3) Å	µ = 0.22 mm⁻¹
b = 16.5165 (6) Å	T = 297 K
c = 12.4930 (4) Å	0.61 × 0.26 × 0.23 mm
β = 121.518 (2)°

Data collection top

Bruker APEXII DUO CCD area-detector diffractometer	5432 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	4148 reflections with I > 2σ(I)
T_min = 0.877, T_max = 0.950	R_int = 0.023
20021 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.039	0 restraints
wR(F²) = 0.119	H-atom parameters constrained
S = 1.02	Δρ_max = 0.31 e Å⁻³
5432 reflections	Δρ_min = −0.17 e Å⁻³
191 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) x, −y+1/2, z−1/2; (ii) x, y, z−1.

Experimental details

Crystal data
Chemical formula	C₁₆H₁₈N₂O₂S
M_r	302.38
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	297
a, b, c (Å)	8.5811 (3), 16.5165 (6), 12.4930 (4)
β (°)	121.518 (2)
V (Å³)	1509.42 (9)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.22
Crystal size (mm)	0.61 × 0.26 × 0.23

Data collection
Diffractometer	Bruker APEXII DUO CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.877, 0.950
No. of measured, independent and observed [I > 2σ(I)] reflections	20021, 5432, 4148
R_int	0.023
(sin θ/λ)_max (Å⁻¹)	0.758

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.039, 0.119, 1.02
No. of reflections	5432
No. of parameters	191
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.31, −0.17

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

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) x, −y+1/2, z−1/2; (ii) x, y, z−1.

Footnotes

‡Thomson Reuters ResearcherID: A-3561-2009.

§Thomson Reuters ResearcherID: A-5523-2009.

Acknowledgements

HKF and CSY thank Universiti Sains Malaysia for the Research University Grant 1001/PFIZIK/811160.

References

Ahn, J. H., Kim, S. J., Park, W. S., Cho, S. Y., Ha, J. D., Kim, S. S., Kang, S. K., Jeong, D. G., Jung, S. K., Lee, S. H., Kim, H. M., Park, S. K., Lee, K. H., Lee, C. W., Ryu, S. E. & Choi, J. K. (2006). Bioorg. Med. Chem. Lett. 16, 2996–2999. Web of Science CrossRef PubMed CAS Google Scholar
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573. CrossRef CAS Web of Science Google Scholar
Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Geronikaki, A., Eleftheriou, P., Vicini, P., Alam, I., Dixit, A. & Saxena, A. K. (2008). J. Med. Chem. 51, 5221–5228. Web of Science CrossRef PubMed CAS Google Scholar
Havrylyuk, D., Zimenkovsky, B., Vasylenko, O., Zaprutko, L., Gzella, A. & Lesyk, R. (2009). Eur. J. Med. Chem. 44, 1396–1404. Web of Science CSD CrossRef PubMed CAS Google Scholar
Lesyk, R., Vladzimirska, O., Holota, S., Zaprutko, L. & Gzella, A. (2007). Eur. J. Med. Chem. 42, 641–648. Web of Science CSD CrossRef PubMed CAS Google Scholar
Lesyk, R. & Zimenkovsky, B. (2004). Curr. Org. Chem. 8, 1547–1577. Web of Science CrossRef CAS Google Scholar
Park, H., Jung, S. K., Jeong, D. G., Ryu, S. E. & Kim, S. J. (2008). Bioorg. Med. Chem. Lett. 18, 2250–2255. Web of Science CrossRef PubMed CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Zimenkovsky, B., Kazmirchuk, G., Zaprutko, L., Paraskiewicz, A., Melzer, E. & Lesyk, R. (2005). Ann. Polish Chem. Soc. 1, 69–72. Google Scholar