S-Phenyl 4-meth­oxy­benzothio­ate

El-Azab, A.S.; Abdel-Aziz, A.A.-M.; El-Subbagh, H.I.; Chantrapromma, S.; Fun, H.-K.

doi:10.1107/S1600536812005454

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 68| Part 4| April 2012| Pages o1074-o1075

doi:10.1107/S1600536812005454

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S-Phenyl 4-methoxybenzothioate

Adel S. El-Azab,^a,^b Alaa A.-M. Abdel-Aziz,^a,^c Hussein I. El-Subbagh,^d Suchada Chantrapromma ^e ‡ and Hoong-Kun Fun ^f ^*§

^aDepartment of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, PO Box 2457, Riyadh 11451, Saudi Arabia, ^bDepartment of Organic Chemistry, Faculty of Pharmacy, Al-Azhar University, Cairo 11884, Egypt, ^cDepartment of Medicinal Chemistry, Faculty of Pharmacy, University of Mansoura, Mansoura 35516, Egypt, ^dDepartment of Pharmaceutical Chemistry, Faculty of Pharmaceutical Sciences and Pharmaceutical Industries, Future University, Cairo 12311, Egypt, ^eCrystal Materials Research Unit, Department of Chemistry, Faculty of Science, Prince of Songkla University, Hat-Yai, Songkhla 90112, Thailand, and ^fX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia
^*Correspondence e-mail: hkfun@usm.my

(Received 30 January 2012; accepted 7 February 2012; online 17 March 2012)

In the molecule of the title thioester, C₁₄H₁₂O₂S, the dihedral angle between the phenyl and benzene rings is 71.8 (3)°. The methoxy group is essentially coplanar with the benezene ring to which it is bonded, with an r.m.s. deviation of 0.0065 (5) Å for the non-H atoms involved. In the crystal, weak C—H⋯π interactions are present.

Related literature

For background to and applications of thioesters, see: Agapiou & Krische (2003 ); Choi et al. (2003 ); El-Azab & Abdel-Aziz (2012 ); Horst et al. (2007 ); Howell et al. (2006 ); Jew et al. (2003 ); Liebeskind & Srogl (2000 ); McGarvey et al. (1986 ); Ozaki et al. (2003 ); Shah et al. (2002 ); Yang & Drueckhammer (2001 ). For related structures and the synthesis of similar compounds, see: Barbero et al. (2003 ). For bond-length data, see: Allen et al. (1987 ).

Experimental

Crystal data

C₁₄H₁₂O₂S
M_r = 244.31
Orthorhombic, P 2₁ 2₁ 2₁
a = 5.4478 (2) Å
b = 8.2149 (3) Å
c = 27.3841 (6) Å
V = 1225.52 (7) Å³
Z = 4
Cu Kα radiation
μ = 2.23 mm⁻¹
T = 296 K
0.58 × 0.22 × 0.17 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.357, T_max = 0.699
7810 measured reflections
2144 independent reflections
1479 reflections with I > 2σ(I)
R_int = 0.050

Refinement

R[F² > 2σ(F²)] = 0.056
wR(F²) = 0.199
S = 1.22
2144 reflections
156 parameters
H-atom parameters constrained
Δρ_max = 0.32 e Å⁻³
Δρ_min = −0.28 e Å⁻³
Absolute structure: Flack (1983 ), 1811 Friedel pairs
Flack parameter: 0.07 (5)

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C1–C6 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3A⋯Cg1ⁱ	0.93	2.96	3.658 (6)	133
Symmetry code: (i) $[-x-1, y-{\script{1\over 2}}, -z+{\script{5\over 2}}]$ .

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/S1600536812005454/lh5413sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812005454/lh5413Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812005454/lh5413Isup3.cml

checkCIF report

Comment top

Thioesters are one of the most useful building blocks for organic transformations such as in application of C-C coupling for the synthesis of carbonyl compounds in asymmetric aldol reactions. Recently, the α-β-unsaturated thioester analogs have been successfully applied for asymmetric additions which allow the access to chiral intermediates for the synthesis of more complex compounds. Furthermore, they were used in natural product synthesis and also are acting as biologically relevant substances finding application for in vivo tumor suppression (Agapiou & Krische (2003); Barbero et al., 2003; Choi et al., 2003; Horst et al., 2007; Howell et al., 2006; Jew et al., 2003; Liebeskind & Srogl 2000; McGarvey et al., 1986; Ozaki et al., 2003; Shah et al., 2002; Yang & Drueckhammer, 2001). Owing to these applications of thioesters, the title compound (I) was synthesized. The molecule is chiral even though it has no chiral center as its mirror image cannot be superposed onto itself. The absolute configuration and crystal structure are reported. We have examined optically the batch of crystals and the morphology is the same for all the crystals in the batch thereby implying that there is no spontaneous resolution.

In the molecule of (I) shown in Fig. 1, the dihedral angle between the phenyl and benzene rings is 71.8 (3)°. The central O1/C7/S1 plane makes dihedral angles of 10.8 (5) and 81.0 (6)° with the C1–C6 and C8–C13 rings, repectively. The methoxy group of the 4-methoxyphenyl group is essentially co-planar with its bound benezene ring with a r.m.s. deviation of 0.0065 (5) Å for the eight non H atoms (C1/C2/C3/C4/C5/C6/O2/C14) and the torsion angle C14—O2—C4—C3 = -2.1 (8)°. The bond distances in (I) are within normal ranges (Allen et al., 1987).

The crystal structure is consolidated by weak C—H···π interactions (Table 1).

Related literature top

For background to and applications of thioesters, see: Agapiou & Krische (2003); Choi et al. (2003); El-Azab & Abdel-Aziz (2012); Horst et al. (2007); Howell et al. (2006); Jew et al. (2003); Liebeskind & Srogl (2000); McGarvey et al. (1986); Ozaki et al. (2003); Shah et al. (2002); Yang & Drueckhammer (2001). For related structures and the synthesis of similar compounds, see: Barbero et al. (2003). For bond-length data, see: Allen et al. (1987).

Experimental top

The title compound was synthesized according to El-Azab & Abdel-Aziz (2012). The trifluoroacetic acid (0.4 equiv) was added dropwise to a stirred solution of carboxylic acid (1 equiv) and thiophenol (1 equiv) in dry CH₃CN (0.01 mol/l) over a period of 15 min at room temperature. After being stirred for 2–5 h at 333 K, the mixture was quenched by adding ammonium chloride solution (5 ml), extracted with ethylacetate, washed with brine and dried over anhydrous sodium sulfate. The product obtained after the evaporation of the solvent was purified by colum chromatography using mixture of hexane and CHCl₃ as eluent. The crystal was obtained by slow evaporation of the eluent system hexane and CHCl₃; m.p. 366-367 K, 97% yield. IR (KBr): 1661 cm^-1 (CO), ¹H NMR (CDCl₃): d 8.06 (d, 2H, J = 8.5 Hz), 7.55–7.54 (m, 2H), 7.48 (m, 3H), 6.99 (t, 2H, J = 4.0 Hz), 2.90 (s, 3H). ¹³C NMR (CDCl₃): d 55.6, 113.9, 127.7, 129.2, 129.4, 129.8, 135.2, 164.0, 188.6.

Structure description top

The crystal structure is consolidated by weak C—H···π interactions (Table 1).

For background to and applications of thioesters, see: Agapiou & Krische (2003); Choi et al. (2003); El-Azab & Abdel-Aziz (2012); Horst et al. (2007); Howell et al. (2006); Jew et al. (2003); Liebeskind & Srogl (2000); McGarvey et al. (1986); Ozaki et al. (2003); Shah et al. (2002); Yang & Drueckhammer (2001). For related structures and the synthesis of similar compounds, see: Barbero et al. (2003). For bond-length data, see: Allen et al. (1987).

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 (I), showing 30% probability displacement ellipsoids and the atom-numbering scheme.

S-Phenyl 4-methoxybenzothioate top

Crystal data top

C₁₄H₁₂O₂S	D_x = 1.324 Mg m⁻³
M_r = 244.31	Melting point = 366–367 K
Orthorhombic, P2₁2₁2₁	Cu Kα radiation, λ = 1.54178 Å
Hall symbol: P 2ac 2ab	Cell parameters from 2144 reflections
a = 5.4478 (2) Å	θ = 3.2–69.4°
b = 8.2149 (3) Å	µ = 2.23 mm⁻¹
c = 27.3841 (6) Å	T = 296 K
V = 1225.52 (7) Å³	Needle, colourless
Z = 4	0.58 × 0.22 × 0.17 mm
F(000) = 512

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	2144 independent reflections
Radiation source: fine-focus sealed tube	1479 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.050
φ and ω scans	θ_max = 69.4°, θ_min = 3.2°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −4→6
T_min = 0.357, T_max = 0.699	k = −9→8
7810 measured reflections	l = −32→29

Refinement top

Refinement on F²	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.056	w = 1/[σ²(F_o²) + (0.0897P)² + 0.2372P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.199	(Δ/σ)_max = 0.001
S = 1.22	Δρ_max = 0.32 e Å⁻³
2144 reflections	Δρ_min = −0.28 e Å⁻³
156 parameters	Extinction correction: SHELXTL (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.025 (3)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983), with 1811 Friedel pairs
Secondary atom site location: difference Fourier map	Absolute structure parameter: 0.07 (5)

Crystal data top

C₁₄H₁₂O₂S	V = 1225.52 (7) Å³
M_r = 244.31	Z = 4
Orthorhombic, P2₁2₁2₁	Cu Kα radiation
a = 5.4478 (2) Å	µ = 2.23 mm⁻¹
b = 8.2149 (3) Å	T = 296 K
c = 27.3841 (6) Å	0.58 × 0.22 × 0.17 mm

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	2144 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	1479 reflections with I > 2σ(I)
T_min = 0.357, T_max = 0.699	R_int = 0.050
7810 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.056	H-atom parameters constrained
wR(F²) = 0.199	Δρ_max = 0.32 e Å⁻³
S = 1.22	Δρ_min = −0.28 e Å⁻³
2144 reflections	Absolute structure: Flack (1983), with 1811 Friedel pairs
156 parameters	Absolute structure parameter: 0.07 (5)
0 restraints

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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	0.2447 (3)	0.2241 (2)	0.88540 (4)	0.0866 (6)
O1	−0.1014 (8)	0.0079 (5)	0.87109 (10)	0.0848 (13)
O2	−0.0150 (7)	−0.0916 (5)	1.10026 (10)	0.0712 (10)
C1	0.0101 (8)	0.0386 (6)	0.95439 (14)	0.0579 (11)
C2	−0.1770 (8)	−0.0607 (6)	0.97065 (16)	0.0641 (12)
H2A	−0.2939	−0.0981	0.9486	0.077*
C3	−0.1940 (8)	−0.1055 (7)	1.01918 (14)	0.0657 (13)
H3A	−0.3225	−0.1713	1.0297	0.079*
C4	−0.0204 (8)	−0.0527 (6)	1.05180 (14)	0.0596 (11)
C5	0.1682 (8)	0.0475 (6)	1.03636 (15)	0.0637 (12)
H5A	0.2841	0.0853	1.0585	0.076*
C6	0.1830 (8)	0.0911 (7)	0.98763 (15)	0.0625 (12)
H6A	0.3117	0.1568	0.9771	0.075*
C7	0.0229 (9)	0.0742 (7)	0.90125 (15)	0.0653 (13)
C8	0.2346 (9)	0.2180 (7)	0.82059 (16)	0.0684 (13)
C9	0.4109 (10)	0.1329 (7)	0.79629 (16)	0.0773 (15)
H9A	0.5299	0.0757	0.8136	0.093*
C10	0.4122 (11)	0.1319 (8)	0.74530 (17)	0.0827 (17)
H10A	0.5297	0.0722	0.7284	0.099*
C11	0.2390 (10)	0.2194 (7)	0.72047 (17)	0.0779 (14)
H11A	0.2402	0.2198	0.6865	0.094*
C12	0.0654 (11)	0.3056 (9)	0.74480 (18)	0.0860 (18)
H12A	−0.0511	0.3651	0.7275	0.103*
C13	0.0619 (11)	0.3049 (8)	0.79550 (19)	0.0818 (16)
H13A	−0.0574	0.3634	0.8123	0.098*
C14	−0.2089 (11)	−0.1900 (9)	1.11832 (18)	0.096 (2)
H14A	−0.1840	−0.2103	1.1525	0.144*
H14B	−0.2115	−0.2915	1.1010	0.144*
H14C	−0.3624	−0.1347	1.1137	0.144*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.1088 (11)	0.0977 (13)	0.0532 (6)	−0.0329 (9)	−0.0016 (6)	−0.0022 (6)
O1	0.088 (3)	0.107 (4)	0.0589 (17)	−0.019 (2)	−0.0185 (16)	0.0018 (19)
O2	0.083 (2)	0.079 (3)	0.0521 (16)	−0.0038 (17)	−0.0032 (13)	0.0042 (16)
C1	0.058 (2)	0.064 (3)	0.052 (2)	0.0023 (19)	−0.0063 (17)	−0.011 (2)
C2	0.061 (3)	0.066 (4)	0.065 (2)	−0.006 (2)	−0.0035 (18)	0.001 (2)
C3	0.061 (3)	0.083 (4)	0.053 (2)	−0.013 (2)	−0.0014 (17)	0.003 (2)
C4	0.066 (3)	0.060 (3)	0.053 (2)	−0.001 (2)	−0.0001 (17)	−0.006 (2)
C5	0.066 (3)	0.069 (4)	0.056 (2)	−0.008 (2)	−0.0074 (17)	0.000 (2)
C6	0.061 (3)	0.066 (4)	0.060 (2)	−0.009 (2)	−0.0048 (18)	−0.001 (2)
C7	0.066 (3)	0.077 (4)	0.053 (2)	0.008 (2)	−0.0078 (18)	−0.012 (2)
C8	0.069 (3)	0.077 (4)	0.058 (2)	−0.008 (3)	−0.0016 (19)	0.005 (2)
C9	0.077 (3)	0.087 (4)	0.068 (3)	0.001 (3)	−0.003 (2)	0.013 (3)
C10	0.080 (3)	0.102 (5)	0.067 (3)	0.004 (3)	0.007 (2)	0.004 (3)
C11	0.085 (3)	0.096 (4)	0.053 (2)	−0.005 (3)	−0.005 (2)	0.011 (2)
C12	0.081 (4)	0.108 (5)	0.069 (3)	0.006 (3)	−0.015 (3)	0.013 (3)
C13	0.080 (3)	0.086 (5)	0.080 (3)	0.007 (3)	0.002 (2)	0.000 (3)
C14	0.103 (4)	0.120 (6)	0.065 (3)	−0.033 (4)	0.004 (3)	0.014 (3)

Geometric parameters (Å, º) top

S1—C8	1.776 (4)	C6—H6A	0.9300
S1—C7	1.779 (6)	C8—C9	1.362 (7)
O1—C7	1.199 (5)	C8—C13	1.366 (7)
O2—C4	1.366 (5)	C9—C10	1.397 (6)
O2—C14	1.419 (6)	C9—H9A	0.9300
C1—C6	1.379 (6)	C10—C11	1.367 (7)
C1—C2	1.380 (6)	C10—H10A	0.9300
C1—C7	1.486 (6)	C11—C12	1.356 (8)
C2—C3	1.382 (6)	C11—H11A	0.9300
C2—H2A	0.9300	C12—C13	1.389 (7)
C3—C4	1.371 (6)	C12—H12A	0.9300
C3—H3A	0.9300	C13—H13A	0.9300
C4—C5	1.383 (6)	C14—H14A	0.9600
C5—C6	1.384 (6)	C14—H14B	0.9600
C5—H5A	0.9300	C14—H14C	0.9600

C8—S1—C7	101.7 (2)	C9—C8—S1	118.7 (4)
C4—O2—C14	117.1 (4)	C13—C8—S1	120.6 (4)
C6—C1—C2	118.5 (4)	C8—C9—C10	119.7 (5)
C6—C1—C7	123.6 (4)	C8—C9—H9A	120.2
C2—C1—C7	117.8 (4)	C10—C9—H9A	120.2
C1—C2—C3	121.1 (4)	C11—C10—C9	119.4 (5)
C1—C2—H2A	119.4	C11—C10—H10A	120.3
C3—C2—H2A	119.4	C9—C10—H10A	120.3
C4—C3—C2	119.7 (4)	C12—C11—C10	120.7 (4)
C4—C3—H3A	120.1	C12—C11—H11A	119.6
C2—C3—H3A	120.1	C10—C11—H11A	119.6
O2—C4—C3	125.0 (4)	C11—C12—C13	119.9 (5)
O2—C4—C5	114.9 (4)	C11—C12—H12A	120.0
C3—C4—C5	120.1 (4)	C13—C12—H12A	120.0
C4—C5—C6	119.5 (4)	C8—C13—C12	119.7 (5)
C4—C5—H5A	120.3	C8—C13—H13A	120.2
C6—C5—H5A	120.3	C12—C13—H13A	120.2
C1—C6—C5	121.0 (4)	O2—C14—H14A	109.5
C1—C6—H6A	119.5	O2—C14—H14B	109.5
C5—C6—H6A	119.5	H14A—C14—H14B	109.5
O1—C7—C1	124.0 (5)	O2—C14—H14C	109.5
O1—C7—S1	122.0 (4)	H14A—C14—H14C	109.5
C1—C7—S1	114.0 (3)	H14B—C14—H14C	109.5
C9—C8—C13	120.5 (5)

C6—C1—C2—C3	0.8 (7)	C6—C1—C7—S1	−12.0 (6)
C7—C1—C2—C3	176.9 (5)	C2—C1—C7—S1	172.1 (3)
C1—C2—C3—C4	−0.9 (8)	C8—S1—C7—O1	−5.6 (5)
C14—O2—C4—C3	−2.2 (8)	C8—S1—C7—C1	173.6 (4)
C14—O2—C4—C5	178.1 (5)	C7—S1—C8—C9	−99.8 (5)
C2—C3—C4—O2	−178.6 (5)	C7—S1—C8—C13	84.1 (5)
C2—C3—C4—C5	1.2 (8)	C13—C8—C9—C10	−1.3 (8)
O2—C4—C5—C6	178.4 (5)	S1—C8—C9—C10	−177.4 (5)
C3—C4—C5—C6	−1.3 (8)	C8—C9—C10—C11	1.4 (9)
C2—C1—C6—C5	−0.9 (8)	C9—C10—C11—C12	−0.6 (9)
C7—C1—C6—C5	−176.8 (5)	C10—C11—C12—C13	−0.3 (9)
C4—C5—C6—C1	1.2 (7)	C9—C8—C13—C12	0.4 (9)
C6—C1—C7—O1	167.1 (5)	S1—C8—C13—C12	176.5 (5)
C2—C1—C7—O1	−8.8 (8)	C11—C12—C13—C8	0.4 (10)

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C1–C6 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3A···Cg1ⁱ	0.93	2.96	3.658 (6)	133

Symmetry code: (i) −x−1, y−1/2, −z+5/2.

Experimental details

Crystal data
Chemical formula	C₁₄H₁₂O₂S
M_r	244.31
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	296
a, b, c (Å)	5.4478 (2), 8.2149 (3), 27.3841 (6)
V (Å³)	1225.52 (7)
Z	4
Radiation type	Cu Kα
µ (mm⁻¹)	2.23
Crystal size (mm)	0.58 × 0.22 × 0.17

Data collection
Diffractometer	Bruker SMART APEXII CCD area-detector
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.357, 0.699
No. of measured, independent and observed [I > 2σ(I)] reflections	7810, 2144, 1479
R_int	0.050
(sin θ/λ)_max (Å⁻¹)	0.607

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.056, 0.199, 1.22
No. of reflections	2144
No. of parameters	156
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.32, −0.28
Absolute structure	Flack (1983), with 1811 Friedel pairs
Absolute structure parameter	0.07 (5)

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 C1–C6 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3A···Cg1ⁱ	0.93	2.96	3.658 (6)	133

Symmetry code: (i) −x−1, y−1/2, −z+5/2.

Footnotes

‡Thomson Reuters ResearcherID: A-5085-2009.

§Alternative address: College of Pharmacy (Visiting Professor), King Saud University, PO Box 2457, Riyadh 11451, Saudi Arabia. Thomson Reuters ResearcherID: A-3561-2009.

Acknowledgements

The authors thank the Deanship of Scientific Research and the Research Center of the College of Pharmacy, King Saud University. The authors also thank Universiti Sains Malaysia for Research University grant No. 1001/PFIZIK/811160. HKF thanks King Saud University, Riyadh, Saudi Arabia, for the award of a Visiting Professorship (23 December 2011 to 14 January 2012).

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Volume 68| Part 4| April 2012| Pages o1074-o1075

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