(E)-3-(2,4-Dichloro­phen­yl)-1-(2-thien­yl)prop-2-en-1-one

Fun, H.-K.; Patil, P.S.; Dharmaprakash, S.M.; Chantrapromma, S.; Razak, I.A.

doi:10.1107/S1600536808026524

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 64| Part 9| September 2008| Pages o1814-o1815

doi:10.1107/S1600536808026524

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(E)-3-(2,4-Dichlorophenyl)-1-(2-thienyl)prop-2-en-1-one

Hoong-Kun Fun,^a ^* P. S. Patil,^b ‡ S. M. Dharmaprakash,^c Suchada Chantrapromma ^d § and Ibrahim Abdul Razak ^a

^aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, ^bDepartment of Physics, KLE Society's KLE Institute of Technology, Gokul Road, Hubli 590 030, India, ^cDepartment of Studies in Physics, Mangalore University, Mangalagangotri, Mangalore 574 199, India, and ^dCrystal Materials Research Unit, Department of Chemistry, Faculty of Science, Prince of Songkla University, Hat-Yai, Songkhla 90112, Thailand
^*Correspondence e-mail: hkfun@usm.my

(Received 2 August 2008; accepted 18 August 2008; online 23 August 2008)

In the title chalcone derivative, C₁₃H₈Cl₂OS, the prop-2-en-1-one unit and the thiophene and 2,4-dichlorophenyl rings are each essentially planar. The interplanar angle between the thiophene and 2,4-dichlorophenyl rings is 19.87 (6)°. Weak intramolecular C—H⋯O and C—H⋯Cl interactions involving the prop-2-en-1-one unit generate an S(5)S(5) ring motif. In the crystal structure, molecules are linked into head-to-tail zigzag chains along the a axis and adjacent chains are cross-linked. These cross-linked chains are arranged into sheets parallel to the ab plane. The crystal structure is stabilized by weak C—H⋯O, C—H⋯Cl and C—H⋯π interactions. A π–π interaction was also observed with a centroid–centroid distance of 3.6845 (6) Å.

Related literature

For details of hydrogen-bond motifs, see: Bernstein et al. (1995 ). For bond-length data, see: Allen et al. (1987 ). For related structures, see, for example: Fun et al. (2008a ,b ). For background on the applications of substituted chalcones, see, for example: Agrinskaya et al. (1999 ); Chopra et al. (2007 ); Goto et al. (1991 ); Gu et al. (2008a ,b ,c ); Patil et al. (2007a ,b ,c ); Sarojini et al. (2006 ); Wang et al. (2004 ).

Experimental

Crystal data

C₁₃H₈Cl₂OS
M_r = 283.16
Monoclinic, P 2₁ /c
a = 9.5701 (4) Å
b = 13.9544 (6) Å
c = 10.4748 (4) Å
β = 118.735 (3)°
V = 1226.59 (9) Å³
Z = 4
Mo Kα radiation
μ = 0.68 mm⁻¹
T = 100.0 (1) K
0.58 × 0.24 × 0.13 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.695, T_max = 0.919
41878 measured reflections
4435 independent reflections
3831 reflections with I > 2σ(I)
R_int = 0.031

Refinement

R[F² > 2σ(F²)] = 0.029
wR(F²) = 0.082
S = 1.06
4435 reflections
162 parameters
H-atom parameters constrained
Δρ_max = 0.60 e Å⁻³
Δρ_min = −0.28 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3A⋯O1ⁱ	0.93	2.52	3.4512 (17)	175
C7—H7A⋯Cl1	0.93	2.68	3.0573 (11)	105
C7—H7A⋯O1	0.93	2.48	2.8116 (17)	101
C10—H10A⋯Cg1ⁱⁱ	0.93	3.33	3.8233 (13)	115
C12—H12A⋯Cg1ⁱⁱⁱ	0.93	2.87	3.6907 (13)	148
Symmetry codes: (i) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (ii) x-1, y, z; (iii) $[-x, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ . Cg1 is the centroid of the S1/C1–C4 ring.

Data collection: APEX2 (Bruker, 2005); cell refinement: APEX2; data reduction: SAINT (Bruker, 2005); 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, 2003 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808026524/ww2127sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808026524/ww2127Isup2.hkl

checkCIF report

Comment top

In the last decades, the second-order nonlinear optical properties of chalcone derivatives have been widely investigated due to their possible applications in a variety of optoelectronic and photonic applications (Agrinskaya et al., 1999; Goto et al., 1991; Patil et al., 2007a, b, c; Sarojini et al., 2006; Wang et al., 2004). These derivatives also exhibit the optical limiting property which is a requirement of protecting the human eye or artificial optical sensor from damaging high-energy lasers (Gu et al., 2008a, b, c). In our continuing systematic study on chalcone derivatives, we report here the structure of the title compound.

In the structure of the title chalcone derivative (Fig. 1), bond lengths and angles are in normal ranges (Allen et al., 1987) and comparable to those in related structures (Fun et al., 2008a, b). The prop-2-en-1-one unit (O1/C5–C7), the thiophene ring and the 2,4-dichlorophenyl ring are individually essentially planar, with maximum deviations of 0.003 (1), 0.024 (1), -0.007 (1)Å for atom C4, C7 and C11, respectively. The total molecule is slightly twisted as indicated by the dihedral angles between the least-squares plane through the prop-2-en-1-one unit with the thiophene and 2,4-dichlorophenyl rings being 7.89 (7)° and 22.45 (7)°, and that between the thiophene and 2,4-dichlorophenyl rings being 19.87 (6)°.

In the structure, both weak intramolecular C7—H7A···O1 and C7—H7A···Cl1 interactions (Table 1) generate S(5) ring motifs (Bernstein et al., 1995). In the crystal structure (Fig. 2) the molecules are linked in head-to-tail zigzag chains along the a-axis by weak C—H···Cl interactions and the adjacent chains were cross-linked by weak C—H···O interactions. These cross-linked chains are arranged into sheets parallel to the ab plane. The crystal is stabilized by weak C—H···O, C—H···Cl and C—H···π interactions (Table 1), π···π interaction was also observed with the Cg₂···Cg₂ distance of 3.6845 (6)Å (symmetry code: -x,1 - y, 1 - z); Cg₁ and Cg₂ are the centroids of S1/C1–C4 and C8–C13 rings.

Related literature top

For details of hydrogen-bond motifs, see: Bernstein et al. (1995). For bond-length data, see: Allen et al. (1987). For related structures, see, for example: Fun et al. (2008a,b). For background on the applications of substituted chalcones, see, for example: Agrinskaya et al. (1999); Chopra et al. (2007); Goto et al. (1991); Gu et al. (2008a,b,c); Patil et al. (2007a,b,c); Sarojini et al. (2006); Wang et al. (2004). Cg1 is the centroid of the S1/C1–C4 ring.

Experimental top

The title compound was synthesized by the condensation of 2,4-dichlorobenzaldehyde (0.01 mol, 1.75 g) with 2-acetylthiophene (0.01 mol, 1.07 ml) in methanol (60 ml) in the presence of a catalytic amount of sodium hydroxide solution (5 ml, 30%). After stirring (6 h), the contents of the flask were poured into ice-cold water (500 ml) and left to stand for 5 h. The resulting crude solid was filtered and dried. Needle colorless single crystals of the title compound suitable for X-Ray structure determination were grown by slow evaporation of the methanol solution at room temperature.

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: APEX2 (Bruker, 2005); data reduction: SAINT (Bruker, 2005); 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, 2003).

Figures top

	Fig. 1. The asymmetric unit of (I), showing 50% probability displacement ellipsoids and the atomic numbering. Weak intramolecular C—H···O and C—H···Cl interactions are drawn as dashed lines.
	Fig. 2. The crystal packing of (I), viewed along the c axis showing the cross-linked chains approximately along the a axis. Hydrogen bonds are drawn as dashed lines.

(E)-3-(2,4-Dichlorophenyl)-1-(2-thienyl)prop-2-en-1-one top

Crystal data top

C₁₃H₈Cl₂OS	F(000) = 576
M_r = 283.16	D_x = 1.533 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4435 reflections
a = 9.5701 (4) Å	θ = 2.4–32.5°
b = 13.9544 (6) Å	µ = 0.68 mm⁻¹
c = 10.4748 (4) Å	T = 100 K
β = 118.735 (3)°	Needle, colorless
V = 1226.59 (9) Å³	0.58 × 0.24 × 0.13 mm
Z = 4

Data collection top

Bruker SMART APEX2 CCD area-detector diffractometer	4435 independent reflections
Radiation source: fine-focus sealed tube	3831 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.031
Detector resolution: 8.33 pixels mm^-1	θ_max = 32.5°, θ_min = 2.4°
ω scans	h = −14→14
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −21→21
T_min = 0.695, T_max = 0.919	l = −15→15
41878 measured reflections

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)] = 0.029	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.082	H-atom parameters constrained
S = 1.07	w = 1/[σ²(F_o²) + (0.0403P)² + 0.4876P] where P = (F_o² + 2F_c²)/3
4435 reflections	(Δ/σ)_max = 0.001
162 parameters	Δρ_max = 0.60 e Å⁻³
0 restraints	Δρ_min = −0.28 e Å⁻³

Crystal data top

C₁₃H₈Cl₂OS	V = 1226.59 (9) Å³
M_r = 283.16	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 9.5701 (4) Å	µ = 0.68 mm⁻¹
b = 13.9544 (6) Å	T = 100 K
c = 10.4748 (4) Å	0.58 × 0.24 × 0.13 mm
β = 118.735 (3)°

Data collection top

Bruker SMART APEX2 CCD area-detector diffractometer	4435 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	3831 reflections with I > 2σ(I)
T_min = 0.695, T_max = 0.919	R_int = 0.031
41878 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.029	0 restraints
wR(F²) = 0.082	H-atom parameters constrained
S = 1.07	Δρ_max = 0.60 e Å⁻³
4435 reflections	Δρ_min = −0.28 e Å⁻³
162 parameters

Special details top

Experimental. The low-temperature data was collected with the Oxford Cyrosystem Cobra low-temperature attachment.

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
Cl1	−0.05796 (3)	0.558919 (18)	0.18442 (3)	0.01990 (7)
Cl2	−0.34903 (3)	0.43921 (2)	0.48214 (3)	0.02181 (7)
S1	0.55248 (3)	0.18039 (2)	0.20853 (3)	0.02097 (7)
O1	0.30678 (11)	0.32994 (6)	0.13125 (9)	0.02122 (16)
C1	0.64865 (14)	0.08866 (9)	0.32542 (13)	0.0239 (2)
H1A	0.7245	0.0504	0.3162	0.042 (5)*
C2	0.60409 (14)	0.07946 (9)	0.43128 (13)	0.0222 (2)
H2A	0.6448	0.0331	0.5039	0.030 (4)*
C3	0.48923 (13)	0.14851 (8)	0.41751 (12)	0.01776 (19)
H3A	0.4462	0.1531	0.4802	0.025 (4)*
C4	0.44866 (12)	0.20851 (7)	0.29930 (11)	0.01483 (17)
C5	0.32870 (12)	0.28469 (7)	0.24030 (11)	0.01551 (18)
C6	0.23178 (13)	0.30140 (8)	0.31373 (11)	0.01662 (18)
H6A	0.2532	0.2670	0.3972	0.033 (4)*
C7	0.11366 (13)	0.36566 (7)	0.26054 (12)	0.01658 (18)
H7A	0.0995	0.4012	0.1800	0.022 (4)*
C8	0.00490 (12)	0.38454 (7)	0.31897 (11)	0.01508 (17)
C9	−0.01998 (13)	0.31711 (8)	0.40561 (12)	0.01814 (19)
H9A	0.0373	0.2601	0.4292	0.032 (4)*
C10	−0.12712 (13)	0.33288 (8)	0.45700 (12)	0.01822 (19)
H10A	−0.1418	0.2872	0.5141	0.030 (4)*
C11	−0.21239 (12)	0.41837 (8)	0.42150 (12)	0.01651 (18)
C12	−0.19070 (12)	0.48797 (7)	0.33822 (11)	0.01626 (18)
H12A	−0.2472	0.5453	0.3164	0.023 (4)*
C13	−0.08277 (12)	0.47006 (7)	0.28828 (11)	0.01535 (18)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.02152 (13)	0.01786 (12)	0.02316 (13)	0.00278 (8)	0.01301 (10)	0.00674 (9)
Cl2	0.02120 (13)	0.02533 (13)	0.02547 (14)	0.00247 (9)	0.01647 (11)	0.00112 (10)
S1	0.02269 (14)	0.02431 (14)	0.02117 (13)	0.00481 (10)	0.01474 (11)	0.00138 (10)
O1	0.0269 (4)	0.0218 (4)	0.0201 (4)	0.0047 (3)	0.0155 (3)	0.0046 (3)
C1	0.0216 (5)	0.0255 (5)	0.0248 (5)	0.0084 (4)	0.0113 (4)	0.0015 (4)
C2	0.0221 (5)	0.0233 (5)	0.0201 (5)	0.0049 (4)	0.0092 (4)	0.0019 (4)
C3	0.0195 (5)	0.0187 (4)	0.0167 (4)	0.0009 (4)	0.0100 (4)	−0.0006 (4)
C4	0.0159 (4)	0.0156 (4)	0.0155 (4)	0.0001 (3)	0.0096 (4)	−0.0013 (3)
C5	0.0176 (4)	0.0152 (4)	0.0154 (4)	−0.0004 (3)	0.0093 (4)	−0.0019 (3)
C6	0.0191 (5)	0.0178 (4)	0.0159 (4)	0.0006 (4)	0.0107 (4)	−0.0001 (3)
C7	0.0191 (4)	0.0160 (4)	0.0178 (4)	0.0001 (3)	0.0114 (4)	−0.0007 (3)
C8	0.0162 (4)	0.0147 (4)	0.0154 (4)	0.0005 (3)	0.0084 (4)	−0.0001 (3)
C9	0.0211 (5)	0.0148 (4)	0.0216 (5)	0.0023 (3)	0.0127 (4)	0.0018 (4)
C10	0.0215 (5)	0.0162 (4)	0.0208 (5)	0.0005 (4)	0.0133 (4)	0.0016 (4)
C11	0.0160 (4)	0.0187 (4)	0.0170 (4)	0.0000 (3)	0.0097 (4)	−0.0015 (3)
C12	0.0155 (4)	0.0162 (4)	0.0173 (4)	0.0018 (3)	0.0081 (4)	0.0006 (3)
C13	0.0158 (4)	0.0148 (4)	0.0154 (4)	−0.0003 (3)	0.0075 (3)	0.0016 (3)

Geometric parameters (Å, º) top

Cl1—C13	1.7396 (10)	C6—C7	1.3367 (15)
Cl2—C11	1.7310 (11)	C6—H6A	0.9300
S1—C1	1.7033 (12)	C7—C8	1.4629 (14)
S1—C4	1.7186 (10)	C7—H7A	0.9300
O1—C5	1.2317 (13)	C8—C13	1.4042 (14)
C1—C2	1.3720 (17)	C8—C9	1.4048 (15)
C1—H1A	0.9425	C9—C10	1.3858 (16)
C2—C3	1.4160 (16)	C9—H9A	0.9300
C2—H2A	0.9300	C10—C11	1.3912 (15)
C3—C4	1.3865 (15)	C10—H10A	0.9301
C3—H3A	0.9302	C11—C12	1.3862 (15)
C4—C5	1.4656 (14)	C12—C13	1.3866 (15)
C5—C6	1.4806 (14)	C12—H12A	0.9299

C1—S1—C4	91.72 (6)	C6—C7—H7A	117.4
C2—C1—S1	112.39 (9)	C8—C7—H7A	117.4
C2—C1—H1A	125.7	C13—C8—C9	116.67 (9)
S1—C1—H1A	121.9	C13—C8—C7	121.62 (9)
C1—C2—C3	112.43 (11)	C9—C8—C7	121.69 (9)
C1—C2—H2A	123.8	C10—C9—C8	122.10 (10)
C3—C2—H2A	123.8	C10—C9—H9A	119.0
C4—C3—C2	111.85 (10)	C8—C9—H9A	118.9
C4—C3—H3A	124.1	C9—C10—C11	118.74 (10)
C2—C3—H3A	124.1	C9—C10—H10A	120.6
C3—C4—C5	129.85 (9)	C11—C10—H10A	120.6
C3—C4—S1	111.60 (8)	C12—C11—C10	121.53 (10)
C5—C4—S1	118.44 (8)	C12—C11—Cl2	118.77 (8)
O1—C5—C4	120.84 (9)	C10—C11—Cl2	119.70 (8)
O1—C5—C6	122.07 (10)	C11—C12—C13	118.37 (10)
C4—C5—C6	117.04 (9)	C11—C12—H12A	120.8
C7—C6—C5	120.30 (10)	C13—C12—H12A	120.8
C7—C6—H6A	119.9	C12—C13—C8	122.57 (9)
C5—C6—H6A	119.8	C12—C13—Cl1	117.25 (8)
C6—C7—C8	125.15 (10)	C8—C13—Cl1	120.18 (8)

C4—S1—C1—C2	−0.23 (10)	C6—C7—C8—C9	−21.13 (17)
S1—C1—C2—C3	−0.06 (14)	C13—C8—C9—C10	0.92 (16)
C1—C2—C3—C4	0.42 (15)	C7—C8—C9—C10	−177.58 (10)
C2—C3—C4—C5	175.55 (11)	C8—C9—C10—C11	−0.07 (17)
C2—C3—C4—S1	−0.59 (12)	C9—C10—C11—C12	−0.93 (17)
C1—S1—C4—C3	0.47 (9)	C9—C10—C11—Cl2	179.10 (9)
C1—S1—C4—C5	−176.16 (9)	C10—C11—C12—C13	0.99 (16)
C3—C4—C5—O1	−178.54 (11)	Cl2—C11—C12—C13	−179.04 (8)
S1—C4—C5—O1	−2.62 (14)	C11—C12—C13—C8	−0.07 (16)
C3—C4—C5—C6	−1.06 (16)	C11—C12—C13—Cl1	−179.86 (8)
S1—C4—C5—C6	174.85 (7)	C9—C8—C13—C12	−0.86 (15)
O1—C5—C6—C7	1.53 (16)	C7—C8—C13—C12	177.65 (10)
C4—C5—C6—C7	−175.91 (10)	C9—C8—C13—Cl1	178.93 (8)
C5—C6—C7—C8	176.55 (10)	C7—C8—C13—Cl1	−2.57 (14)
C6—C7—C8—C13	160.45 (11)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3A···O1ⁱ	0.93	2.52	3.4512 (17)	175
C7—H7A···Cl1	0.93	2.68	3.0573 (11)	105
C7—H7A···O1	0.93	2.48	2.8116 (17)	101
C10—H10A···Cg1ⁱⁱ	0.93	3.33	3.8233 (13)	115
C12—H12A···Cg1ⁱⁱⁱ	0.93	2.87	3.6907 (13)	148

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

Experimental details

Crystal data
Chemical formula	C₁₃H₈Cl₂OS
M_r	283.16
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	9.5701 (4), 13.9544 (6), 10.4748 (4)
β (°)	118.735 (3)
V (Å³)	1226.59 (9)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.68
Crystal size (mm)	0.58 × 0.24 × 0.13

Data collection
Diffractometer	Bruker SMART APEX2 CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.695, 0.919
No. of measured, independent and observed [I > 2σ(I)] reflections	41878, 4435, 3831
R_int	0.031
(sin θ/λ)_max (Å⁻¹)	0.756

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.029, 0.082, 1.07
No. of reflections	4435
No. of parameters	162
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.60, −0.28

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3A···O1ⁱ	0.93	2.5238	3.4512 (17)	175
C7—H7A···Cl1	0.93	2.6803	3.0573 (11)	105
C7—H7A···O1	0.93	2.4816	2.8116 (17)	101
C10—H10A···Cg1ⁱⁱ	0.93	3.3310	3.8233 (13)	115
C12—H12A···Cg1ⁱⁱⁱ	0.93	2.8690	3.6907 (13)	148

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

Footnotes

‡Department of Studies in Physics, Mangalore University, Mangalagangotri, Mangalore 574 199, India.

§Additional correspondence author, e-mail: suchada.c@psu.ac.th.

Acknowledgements

This work is supported by the Department of Science and Technology (DST), Government of India under grant No. SR/S2/LOP-17/2006. IAR and HKF thank Universiti Sains Malaysia and the Malaysian Government for the FRGS research grant No. 203/PFIZIK/671064. SC thanks Prince of Songkla University for generous support. The authors also thank Universiti Sains Malaysia for the Research University Golden Goose grant No. 1001/PFIZIK/811012.

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