3-Benzyl-2-phenyl-1,3-thia­zolidin-4-one

Fun, H.-K.; Hemamalini, M.; Shanmugavelan, P.; Ponnuswamy, A.; Jagatheesan, R.

doi:10.1107/S1600536811037706

organic compounds

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ISSN: 2056-9890

Volume 67| Part 10| October 2011| Page o2706

https://doi.org/10.1107/S1600536811037706

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3-Benzyl-2-phenyl-1,3-thiazolidin-4-one

Hoong-Kun Fun,^a ^*‡ Madhukar Hemamalini,^a Poovan Shanmugavelan,^b Alagusundaram Ponnuswamy ^b and Rathinavel Jagatheesan ^c

^aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, ^bDepartment of Organic Chemistry, School of Chemistry, Madurai Kamaraj University, Madurai 625 021, Tamil Nadu, India, and ^cDepartment of Chemistry, Thanthai Hans Roever College, Perambalur 621 212, Tamil Nadu, India
^*Correspondence e-mail: hkfun@usm.my

(Received 12 September 2011; accepted 15 September 2011; online 30 September 2011)

In the title compound, C₁₆H₁₅NOS, the thiazolidine ring, which is essentially planar [maximum deviation = 0.071 (2) Å], makes dihedral angles of 88.01 (8) and 87.21 (8)° with the terminal phenyl rings. The dihedral angle between the phenyl rings is 49.45 (5)°. In the crystal, molecules are linked by a weak intermolecular C—H⋯O hydrogen bond, forming a supramolecular chain along the b axis. Furthermore, the crystal packing is stabilized by a weak C—H⋯π interaction.

Related literature

For details and applications of thiazolidine-4-ones, see: Dutta et al. (1990 ); Jadhav & Ingle (1978 ); Gursoy & Terzioglu (2005 ); Rawal et al. (2007 ); Shrivastava et al. (2005 ); Look et al. (1996 ); Anders et al. (2001 ); Barreca et al. (2001 ); Diurno et al. (1992 ).

Experimental

Crystal data

C₁₆H₁₅NOS
M_r = 269.35
Monoclinic, P 2₁ /c
a = 13.5734 (15) Å
b = 10.1402 (11) Å
c = 10.1496 (11) Å
β = 104.305 (2)°
V = 1353.6 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.23 mm⁻¹
T = 296 K
0.41 × 0.19 × 0.06 mm

Data collection

Bruker APEXII DUO CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.913, T_max = 0.985
21164 measured reflections
3990 independent reflections
2813 reflections with I > 2σ(I)
R_int = 0.041

Refinement

R[F² > 2σ(F²)] = 0.040
wR(F²) = 0.112
S = 1.05
3990 reflections
172 parameters
H-atom parameters constrained
Δρ_max = 0.21 e Å⁻³
Δρ_min = −0.25 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C11–C16 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C14—H14A⋯O1ⁱ	0.93	2.47	3.323 (2)	153
C2—H2A⋯Cg1ⁱⁱ	0.93	2.99	3.705 (3)	134
Symmetry codes: (i) x, y-1, z; (ii) $[x, -y-{\script{1\over 2}}, z-{\script{3\over 2}}]$ .

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: https://doi.org/10.1107/S1600536811037706/is2778sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536811037706/is2778Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536811037706/is2778Isup3.cml

checkCIF report

Comment top

One of the main objectives of organic and medicinal chemistry is the design, synthesis and production of molecules having value as human therapeutic agents. During the past decade, combinatorial chemistry has provided access to chemical libraries based on privileged structures with heterocyclic moiety receiving special attention as they belong to a class of compounds with proven utility in medicinal chemistry. There are numerous biologically active molecules with five-membered rings, containing two hetero atoms. Among them, thiazolidin-4-ones are the most extensively investigated class of compounds, which have many interesting activity profiles namely bactericidal (Dutta et al., 1990), antifungal (Jadhav & Ingle, 1978), anticonvulsant (Gursoy & Terzioglu, 2005), anti-HIV (Rawal et al., 2007), antituberculotic (Shrivastava et al., 2005), COX-1 inhibitors (Look et al., 1996), inhibitors of the bacterial enzyme MurB (Anders et al., 2001), non-nucleoside inhibitors of HIV-RT (Barreca et al., 2001) and anti-histaminic agents (Diurno et al., 1992).

The asymmetric unit of the title compound is shown in Fig. 1. The thiazolidine (S1/N1/C8–C10) ring is essentially planar, with a maximum deviation of 0.071 (2) Å for atom C10. The central thiazolidine (S1/N1/C8–C10) ring makes dihedral angles of 88.01 (8) and 87.21 (8)° with the terminal phenyl (C1–C6) and (C11–C16) rings, respectively. The dihedral angle between the phenyl (C1–C6) and (C11–C16) rings is 49.45 (5)°.

In the crystal structure, (Fig. 2), the molecules are linked by intermolecular weak C—H···O hydrogen bonds forming supramolecular chains along the b-axis. Furthermore, the crystal packing is stabilized by weak C—H···π interactions involving the C11–C16 ring.

Related literature top

For details and applications of thiazolidine-4-ones, see: Dutta et al. (1990); Jadhav & Ingle (1978); Gursoy & Terzioglu (2005); Rawal et al. (2007); Shrivastava et al. (2005); Look et al. (1996); Anders et al. (2001); Barreca et al. (2001); Diurno et al. (1992).

Experimental top

To a well ground intimate mixture of triphenyl phosphine (0.43 g, 1.6 mmol) and benzaldehyde, (0.15 g, 1.5 mmol) in a microwave vial (10 ml) equipped with a magnetic stirring bar, benzylazide, (0.2 g, 1.5 mmol) was added in drop with stirring. Stirring was continued until liberation of nitrogen ceased and then mercaptoacetic acid, (0.15 g, 1.6 mmol) was added to the above mixture and the reaction vessel was sealed with a septum. It was then placed into the cavity of a focused monomode microwave reactor (CEM Discover, benchmate) and operated at 150°C (temperature monitored by a built-in IR sensor), power 80W for 10 minutes. The reaction temperature was maintained by modulating the power level of the reactor. The reaction mixture was allowed to stand at room temperature. Then the residue was purified by column chromatography on silica (petrolium ether–ethyl acetate, 94:6) to afford the 3-benzyl-2-phenylthiazolidin-4-one. Yield: 0.38g (95%); m.p. 152–155°C.

Structure description top

For details and applications of thiazolidine-4-ones, see: Dutta et al. (1990); Jadhav & Ingle (1978); Gursoy & Terzioglu (2005); Rawal et al. (2007); Shrivastava et al. (2005); Look et al. (1996); Anders et al. (2001); Barreca et al. (2001); Diurno et al. (1992).

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. An ORTEP view of the title compound, showing 30% probability displacement ellipsoids.
	Fig. 2. The crystal packing of the title compound, viewed along the a axis.

3-Benzyl-2-phenyl-1,3-thiazolidin-4-one top

Crystal data top

C₁₆H₁₅NOS	F(000) = 568
M_r = 269.35	D_x = 1.322 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4044 reflections
a = 13.5734 (15) Å	θ = 2.9–24.9°
b = 10.1402 (11) Å	µ = 0.23 mm⁻¹
c = 10.1496 (11) Å	T = 296 K
β = 104.305 (2)°	Plate, colourless
V = 1353.6 (3) Å³	0.41 × 0.19 × 0.06 mm
Z = 4

Data collection top

Bruker APEXII DUO CCD area-detector diffractometer	3990 independent reflections
Radiation source: fine-focus sealed tube	2813 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.041
φ and ω scans	θ_max = 30.2°, θ_min = 1.6°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −19→19
T_min = 0.913, T_max = 0.985	k = −14→14
21164 measured reflections	l = −14→14

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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.112	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0448P)² + 0.2789P] where P = (F_o² + 2F_c²)/3
3990 reflections	(Δ/σ)_max = 0.001
172 parameters	Δρ_max = 0.21 e Å⁻³
0 restraints	Δρ_min = −0.25 e Å⁻³

Crystal data top

C₁₆H₁₅NOS	V = 1353.6 (3) Å³
M_r = 269.35	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 13.5734 (15) Å	µ = 0.23 mm⁻¹
b = 10.1402 (11) Å	T = 296 K
c = 10.1496 (11) Å	0.41 × 0.19 × 0.06 mm
β = 104.305 (2)°

Data collection top

Bruker APEXII DUO CCD area-detector diffractometer	3990 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	2813 reflections with I > 2σ(I)
T_min = 0.913, T_max = 0.985	R_int = 0.041
21164 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.040	0 restraints
wR(F²) = 0.112	H-atom parameters constrained
S = 1.05	Δρ_max = 0.21 e Å⁻³
3990 reflections	Δρ_min = −0.25 e Å⁻³
172 parameters

Special details top

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
S1	0.04954 (3)	0.22379 (4)	0.22886 (4)	0.04505 (12)
O1	0.16669 (11)	0.46692 (11)	0.51751 (13)	0.0650 (4)
N1	0.21308 (9)	0.28385 (11)	0.41853 (12)	0.0389 (3)
C1	0.34627 (12)	0.44309 (17)	0.30014 (17)	0.0510 (4)
H1A	0.2783	0.4676	0.2838	0.061*
C2	0.40708 (14)	0.49962 (19)	0.22451 (19)	0.0582 (4)
H2A	0.3798	0.5617	0.1580	0.070*
C3	0.50706 (14)	0.4646 (2)	0.2471 (2)	0.0637 (5)
H3A	0.5481	0.5024	0.1963	0.076*
C4	0.54623 (15)	0.3732 (2)	0.3454 (3)	0.0810 (7)
H4A	0.6143	0.3492	0.3613	0.097*
C5	0.48589 (14)	0.3161 (2)	0.4212 (2)	0.0650 (5)
H5A	0.5136	0.2538	0.4873	0.078*
C6	0.38484 (11)	0.35067 (14)	0.39972 (15)	0.0410 (3)
C7	0.32037 (12)	0.29270 (17)	0.48752 (16)	0.0479 (4)
H7A	0.3454	0.2052	0.5166	0.057*
H7B	0.3278	0.3467	0.5683	0.057*
C8	0.14552 (12)	0.37589 (14)	0.43636 (15)	0.0434 (3)
C9	0.04128 (13)	0.35455 (17)	0.34511 (19)	0.0533 (4)
H9A	0.0173	0.4347	0.2953	0.064*
H9B	−0.0061	0.3309	0.3987	0.064*
C10	0.17936 (10)	0.17886 (13)	0.32051 (14)	0.0358 (3)
H10A	0.2225	0.1788	0.2560	0.043*
C11	0.18426 (10)	0.04347 (13)	0.38516 (13)	0.0350 (3)
C12	0.14070 (11)	0.02045 (14)	0.49347 (15)	0.0420 (3)
H12A	0.1104	0.0896	0.5291	0.050*
C13	0.14219 (12)	−0.10439 (16)	0.54857 (17)	0.0499 (4)
H13A	0.1127	−0.1188	0.6209	0.060*
C14	0.18706 (13)	−0.20754 (16)	0.49698 (19)	0.0547 (4)
H14A	0.1879	−0.2915	0.5342	0.066*
C15	0.23077 (14)	−0.18557 (16)	0.38958 (19)	0.0561 (4)
H15A	0.2611	−0.2550	0.3544	0.067*
C16	0.22959 (12)	−0.06032 (15)	0.33392 (16)	0.0455 (4)
H16A	0.2594	−0.0461	0.2619	0.055*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0441 (2)	0.0416 (2)	0.0451 (2)	−0.00081 (16)	0.00278 (16)	0.00479 (16)
O1	0.0919 (10)	0.0400 (6)	0.0633 (7)	−0.0033 (6)	0.0195 (7)	−0.0119 (6)
N1	0.0399 (6)	0.0325 (6)	0.0436 (6)	−0.0060 (5)	0.0088 (5)	−0.0002 (5)
C1	0.0404 (8)	0.0553 (10)	0.0561 (9)	0.0005 (7)	0.0099 (7)	0.0130 (7)
C2	0.0548 (10)	0.0599 (11)	0.0594 (10)	−0.0048 (8)	0.0132 (8)	0.0154 (8)
C3	0.0508 (10)	0.0721 (13)	0.0721 (12)	−0.0090 (9)	0.0225 (9)	0.0089 (10)
C4	0.0441 (10)	0.0872 (16)	0.1158 (18)	0.0105 (10)	0.0273 (11)	0.0296 (14)
C5	0.0480 (10)	0.0596 (11)	0.0852 (13)	0.0083 (8)	0.0119 (9)	0.0229 (10)
C6	0.0383 (7)	0.0363 (7)	0.0452 (8)	−0.0057 (6)	0.0041 (6)	−0.0011 (6)
C7	0.0456 (8)	0.0481 (9)	0.0450 (8)	−0.0090 (7)	0.0020 (7)	0.0074 (7)
C8	0.0561 (9)	0.0309 (7)	0.0462 (8)	−0.0036 (6)	0.0185 (7)	0.0023 (6)
C9	0.0496 (9)	0.0456 (9)	0.0662 (10)	0.0059 (7)	0.0173 (8)	−0.0016 (8)
C10	0.0372 (7)	0.0346 (7)	0.0369 (7)	−0.0029 (5)	0.0117 (5)	−0.0001 (5)
C11	0.0339 (7)	0.0319 (6)	0.0382 (7)	−0.0008 (5)	0.0069 (5)	−0.0012 (5)
C12	0.0450 (8)	0.0365 (7)	0.0472 (8)	−0.0005 (6)	0.0165 (6)	0.0010 (6)
C13	0.0495 (9)	0.0448 (9)	0.0555 (9)	−0.0074 (7)	0.0130 (7)	0.0118 (7)
C14	0.0547 (10)	0.0337 (8)	0.0667 (11)	−0.0038 (7)	−0.0020 (8)	0.0079 (7)
C15	0.0611 (11)	0.0368 (8)	0.0649 (11)	0.0126 (7)	0.0050 (9)	−0.0067 (7)
C16	0.0471 (8)	0.0443 (8)	0.0451 (8)	0.0074 (7)	0.0111 (7)	−0.0034 (6)

Geometric parameters (Å, º) top

S1—C9	1.7967 (17)	C7—H7A	0.9700
S1—C10	1.8352 (14)	C7—H7B	0.9700
O1—C8	1.2231 (18)	C8—C9	1.503 (2)
N1—C8	1.3515 (19)	C9—H9A	0.9700
N1—C10	1.4518 (18)	C9—H9B	0.9700
N1—C7	1.4544 (19)	C10—C11	1.5160 (19)
C1—C2	1.383 (2)	C10—H10A	0.9800
C1—C6	1.383 (2)	C11—C16	1.3838 (19)
C1—H1A	0.9300	C11—C12	1.391 (2)
C2—C3	1.366 (3)	C12—C13	1.382 (2)
C2—H2A	0.9300	C12—H12A	0.9300
C3—C4	1.369 (3)	C13—C14	1.377 (2)
C3—H3A	0.9300	C13—H13A	0.9300
C4—C5	1.382 (3)	C14—C15	1.382 (3)
C4—H4A	0.9300	C14—H14A	0.9300
C5—C6	1.380 (2)	C15—C16	1.389 (2)
C5—H5A	0.9300	C15—H15A	0.9300
C6—C7	1.513 (2)	C16—H16A	0.9300

C9—S1—C10	93.34 (7)	C8—C9—S1	107.99 (11)
C8—N1—C10	119.26 (12)	C8—C9—H9A	110.1
C8—N1—C7	121.65 (13)	S1—C9—H9A	110.1
C10—N1—C7	118.93 (12)	C8—C9—H9B	110.1
C2—C1—C6	121.10 (15)	S1—C9—H9B	110.1
C2—C1—H1A	119.4	H9A—C9—H9B	108.4
C6—C1—H1A	119.4	N1—C10—C11	113.25 (11)
C3—C2—C1	120.23 (17)	N1—C10—S1	105.43 (9)
C3—C2—H2A	119.9	C11—C10—S1	112.22 (9)
C1—C2—H2A	119.9	N1—C10—H10A	108.6
C2—C3—C4	119.27 (17)	C11—C10—H10A	108.6
C2—C3—H3A	120.4	S1—C10—H10A	108.6
C4—C3—H3A	120.4	C16—C11—C12	119.00 (13)
C3—C4—C5	120.83 (18)	C16—C11—C10	120.14 (13)
C3—C4—H4A	119.6	C12—C11—C10	120.83 (12)
C5—C4—H4A	119.6	C13—C12—C11	120.47 (14)
C6—C5—C4	120.54 (17)	C13—C12—H12A	119.8
C6—C5—H5A	119.7	C11—C12—H12A	119.8
C4—C5—H5A	119.7	C14—C13—C12	120.36 (16)
C5—C6—C1	118.02 (15)	C14—C13—H13A	119.8
C5—C6—C7	120.33 (14)	C12—C13—H13A	119.8
C1—C6—C7	121.60 (14)	C13—C14—C15	119.60 (15)
N1—C7—C6	113.35 (12)	C13—C14—H14A	120.2
N1—C7—H7A	108.9	C15—C14—H14A	120.2
C6—C7—H7A	108.9	C14—C15—C16	120.29 (15)
N1—C7—H7B	108.9	C14—C15—H15A	119.9
C6—C7—H7B	108.9	C16—C15—H15A	119.9
H7A—C7—H7B	107.7	C11—C16—C15	120.28 (15)
O1—C8—N1	123.85 (15)	C11—C16—H16A	119.9
O1—C8—C9	123.53 (15)	C15—C16—H16A	119.9
N1—C8—C9	112.62 (13)

C6—C1—C2—C3	0.1 (3)	C8—N1—C10—C11	−114.56 (14)
C1—C2—C3—C4	−0.1 (3)	C7—N1—C10—C11	69.99 (16)
C2—C3—C4—C5	0.2 (4)	C8—N1—C10—S1	8.50 (15)
C3—C4—C5—C6	−0.3 (4)	C7—N1—C10—S1	−166.95 (10)
C4—C5—C6—C1	0.3 (3)	C9—S1—C10—N1	−10.43 (10)
C4—C5—C6—C7	−177.10 (19)	C9—S1—C10—C11	113.28 (11)
C2—C1—C6—C5	−0.2 (3)	N1—C10—C11—C16	−131.16 (14)
C2—C1—C6—C7	177.17 (16)	S1—C10—C11—C16	109.62 (13)
C8—N1—C7—C6	−98.30 (17)	N1—C10—C11—C12	50.93 (18)
C10—N1—C7—C6	77.04 (17)	S1—C10—C11—C12	−68.30 (15)
C5—C6—C7—N1	−151.78 (16)	C16—C11—C12—C13	−0.4 (2)
C1—C6—C7—N1	30.9 (2)	C10—C11—C12—C13	177.59 (13)
C10—N1—C8—O1	179.17 (14)	C11—C12—C13—C14	0.1 (2)
C7—N1—C8—O1	−5.5 (2)	C12—C13—C14—C15	0.0 (3)
C10—N1—C8—C9	−1.01 (18)	C13—C14—C15—C16	0.0 (3)
C7—N1—C8—C9	174.31 (13)	C12—C11—C16—C15	0.4 (2)
O1—C8—C9—S1	172.54 (13)	C10—C11—C16—C15	−177.53 (14)
N1—C8—C9—S1	−7.28 (16)	C14—C15—C16—C11	−0.3 (2)
C10—S1—C9—C8	10.22 (12)

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C11–C16 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C14—H14A···O1ⁱ	0.93	2.47	3.323 (2)	153
C2—H2A···Cg1ⁱⁱ	0.93	2.99	3.705 (3)	134

Symmetry codes: (i) x, y−1, z; (ii) x, −y−1/2, z−3/2.

Experimental details

Crystal data
Chemical formula	C₁₆H₁₅NOS
M_r	269.35
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	13.5734 (15), 10.1402 (11), 10.1496 (11)
β (°)	104.305 (2)
V (Å³)	1353.6 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.23
Crystal size (mm)	0.41 × 0.19 × 0.06

Data collection
Diffractometer	Bruker APEXII DUO CCD area-detector
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.913, 0.985
No. of measured, independent and observed [I > 2σ(I)] reflections	21164, 3990, 2813
R_int	0.041
(sin θ/λ)_max (Å⁻¹)	0.707

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.040, 0.112, 1.05
No. of reflections	3990
No. of parameters	172
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.21, −0.25

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

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C11–C16 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C14—H14A···O1ⁱ	0.93	2.47	3.323 (2)	153
C2—H2A···Cg1ⁱⁱ	0.93	2.99	3.705 (3)	134

Symmetry codes: (i) x, y−1, z; (ii) x, −y−1/2, z−3/2.

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 thanks Universiti Sains Malaysia for a post-doctoral research fellowship.

References

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