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

Fun, H.-K.; Hemamalini, M.; Lobo, P.L.; Prasad, D.J.; Poojary, B.

doi:10.1107/S1600536811040785

organic compounds

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ISSN: 2056-9890

Volume 67| Part 11| November 2011| Page o2884

doi:10.1107/S1600536811040785

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

Hoong-Kun Fun,^a ^*‡ Madhukar Hemamalini,^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, Mangalagangothri 574 199, Mangalore, Karnataka, India
^*Correspondence e-mail: hkfun@usm.my

(Received 3 October 2011; accepted 4 October 2011; online 8 October 2011)

In the title compound, C₁₅H₁₄Cl₂N₂OS, the piperidine ring adopts a chair conformation. The dihedral angle between the thiazolidine ring and the dichlorobenzene ring is 9.30 (4)°; this near coplanar conformation is stabilized by the formation of an intramolecular C—H⋯S hydrogen bond, which generates an S(6) ring. In the crystal, molecules are linked by C—H⋯O hydrogen bonds, forming [001] chains. Weak π–π interactions [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_r = 341.24
Monoclinic, C 2/c
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[F² > 2σ(F²)] = 0.026
wR(F²) = 0.074
S = 1.03
6673 reflections
190 parameters
H-atom parameters constrained
Δρ_max = 0.52 e Å⁻³
Δρ_min = −0.19 e Å⁻³

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) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (ii) $[x, -y+1, z-{\script{1\over 2}}]$ .

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/S1600536811040785/hb6435sup1.cif

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

Supporting information file. DOI: 10.1107/S1600536811040785/hb6435Isup3.cml

checkCIF report

Comment top

The 4-thiazolidinone ring system is a core structure in various synthetic compounds displaying a broad spectrum of biological activities (Lesyk & Zimenkovsky, 2004), including an anticancer effect (Lesyk et al., 2007; Havrylyuk et al., 2009). The mechanisms of antitumor activity by 4-thiazolidinones and related heterocycles may be associated with their affinities to anticancer bio-targets, such as phosphatase of a regenerating liver (PRL-3) (Ahn et al., 2006; Park et al., 2008) and nonmembrane 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 the title compound, (I), (Fig. 1).

The piperidine ((N2/C11–C15) ring adopts a chair conformation [Q = 0.5462 (10) Å; θ = 5.78 (10)° and ϕ = 206.6 (10)°; Cremer & Pople, 1975]. The central thiazolidine (S1/N1/C8–C10) ring makes dihedral angles of 21.18 (4)° and 9.30 (4)° with the terminal piperidine (N2/C11–C15) and phenyl (C1–C6) rings. The corresponding angle between the piperidine and phenyl (N2/C11–C15)/(C1–C6) rings is 13.69 (4)°. An intramolecular C1—H1A···S1 hydrogen bond generates an S(6) (Bernstein et al., 1995) ring motif.

In the crystal structure, (Fig. 2), the molecules are connected via intermolecular C—H···O (Table 1) hydrogen bonds forming one-dimensional supramolecular chains along the c-axis. The crystal structure is further stabilized by weak π–π interactions between the thiazolidine (Cg1; S1/N1/C8–C10) and phenyl (Cg3; C1–C6) rings [Cg1···Cg3 = 3.5460 (5) Å; 1/2-x, 3/2-y, 1-z].

Related literature top

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 top

An equimolar mixture of 2-(4-methylsulfanylphenyl)acetohydrazide and 4-chlorobenzaldehyde was refluxed for four hours in the presence of few drops of acid catalyst and ethanol as solvent. The compound obtained was filtered, washed, dried and recrystalised from ethanol to yield brown blocks of (I).

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 asymmetric unit of the title compound, showing 50% probability displacement ellipsoids. An intramolecular hydrogen bond is shown by a dashed line.
	Fig. 2. The crystal packing of the title compound (I).

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

Crystal data top

C₁₅H₁₄Cl₂N₂OS	F(000) = 1408
M_r = 341.24	D_x = 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

Data collection top

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

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)] = 0.026	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.074	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0364P)² + 1.7424P] where P = (F_o² + 2F_c²)/3
6673 reflections	(Δ/σ)_max = 0.002
190 parameters	Δρ_max = 0.52 e Å⁻³
0 restraints	Δρ_min = −0.19 e Å⁻³

Crystal data top

C₁₅H₁₄Cl₂N₂OS	V = 2963.17 (6) Å³
M_r = 341.24	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 28.5303 (3) Å	µ = 0.58 mm⁻¹
b = 7.4915 (1) Å	T = 100 K
c = 15.4789 (2) Å	0.44 × 0.25 × 0.13 mm
β = 116.407 (1)°

Data collection top

Bruker SMART APEXII CCD diffractometer	6673 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	5955 reflections with I > 2σ(I)
T_min = 0.783, T_max = 0.928	R_int = 0.024
46944 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.026	0 restraints
wR(F²) = 0.074	H-atom parameters constrained
S = 1.03	Δρ_max = 0.52 e Å⁻³
6673 reflections	Δρ_min = −0.19 e Å⁻³
190 parameters

Special details top

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.

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

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) −x+1/2, y−1/2, −z+3/2; (ii) x, −y+1, z−1/2.

Experimental details

Crystal data
Chemical formula	C₁₅H₁₄Cl₂N₂OS
M_r	341.24
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	100
a, b, c (Å)	28.5303 (3), 7.4915 (1), 15.4789 (2)
β (°)	116.407 (1)
V (Å³)	2963.17 (6)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.58
Crystal size (mm)	0.44 × 0.25 × 0.13

Data collection
Diffractometer	Bruker SMART APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.783, 0.928
No. of measured, independent and observed [I > 2σ(I)] reflections	46944, 6673, 5955
R_int	0.024
(sin θ/λ)_max (Å⁻¹)	0.815

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.026, 0.074, 1.03
No. of reflections	6673
No. of parameters	190
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.52, −0.19

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
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) −x+1/2, y−1/2, −z+3/2; (ii) x, −y+1, z−1/2.

Footnotes

‡Thomson Reuters ResearcherID: A-3561-2009.

Acknowledgements

HKF and MH thank the Malaysian Government and Universiti Sains Malaysia for the Research University grant No. 1001/PFIZIK/811160. MH also thanks Universiti Sains Malaysia for a post-doctoral research fellowship.

References

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