(E)-N′-(3,3-Diphenyl­allyl­idene)-p-toluene­sulfonohydrazide

Mehrabi, H.; Kia, R.

doi:10.1107/S1600536809013269

organic compounds

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ISSN: 2056-9890

Volume 65| Part 5| May 2009| Page o1056

doi:10.1107/S1600536809013269

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(E)-N′-(3,3-Diphenylallylidene)-p-toluenesulfonohydrazide

Hossein Mehrabi ^a ^* and Reza Kia ^b ‡

^aDepartment of Chemistry, Vali-e-Asr University of Rafsanjan, Rafsanjan 77176, Iran, and ^bX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia
^*Correspondence e-mail: mehraby_h@yahoo.com

(Received 6 April 2009; accepted 7 April 2009; online 18 April 2009)

In the title compound, C₂₂H₂₀N₂O₂S, the molecule adopts a twisted E configuration around the C=N bond. The two phenyl rings are twisted from each other, making a dihedral angle of 78.00 (12)°. The methyl-substituted benzene ring makes dihedral angles of 32.37 (14) and 69.70 (12)° with the two phenyl rings. In the crystal structure, molecules are linked into extended chains along the b axis through intermolecular N—H⋯O hydrogen bonds.

Related literature

For related compounds and their bioactivities, see; for example, Mehrabi et al. (2008 ); Tabatabaee et al. (2007 ); Ali et al. (2007 ); Tierney et al. 2006 ; Krygowski et al. (1998 ); Kayser et al. (2004 ). For bond-length data, see: Allen et al. (1987 ).

Experimental

Crystal data

C₂₂H₂₀N₂O₂S
M_r = 376.46
Monoclinic, P 2₁ /n
a = 14.785 (3) Å
b = 6.2179 (12) Å
c = 22.519 (5) Å
β = 102.64 (3)°
V = 2020.0 (7) Å³
Z = 4
Mo Kα radiation
μ = 0.18 mm⁻¹
T = 294 K
0.50 × 0.28 × 0.12 mm

Data collection

Stoe IPDS-II diffractometer
Absorption correction: numerical (X-RED32; Stoe & Cie, 2005 ) T_min = 0.940, T_max = 0.980
5327 measured reflections
5327 independent reflections
4220 reflections with I > 2σ(I)

Refinement

R[F² > 2σ(F²)] = 0.057
wR(F²) = 0.156
S = 1.10
5327 reflections
249 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.21 e Å⁻³
Δρ_min = −0.26 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H1N2⋯O2ⁱ	0.82 (2)	2.11 (2)	2.927 (2)	173 (2)
Symmetry code: (i) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: X-AREA (Stoe & Cie, 2005); cell refinement: X-AREA; data reduction: X-AREA; 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/S1600536809013269/at2762sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809013269/at2762Isup2.hkl

checkCIF report

Comment top

Sulfonamides were the first class of antimicrobial agents to be discovered. They inhibit dihydropteroate synthetase in the bacterial folic acid pathway. Although their clinical role has diminished, they are still useful in certain situations, because of its efficacy and low cost (Krygowski et al., 1998). Sulfonamides (sulfanilamide, sulfamethoxazole, sulfafurazole) are structural analogs of p-aminobenzoic acid (PABA) and compete with PABA to block its conversion to dihydrofolic acid. These agents are generally used in combination with other drugs (usually sulfonamides) to prevent or treat a number of bacterial and parasitic infections (Tierney et al., 2006). Some of the applications of sulfonamides are the anti-infective agents of choice, as follows: Bacteria as Human Pathogens, such as Antibiotic Treatment of Infections Caused by Gram-Positive Bacilli and Gram-negative Haemophilus ducreyi and Haemophilus aegyptius, Alternative Drug for treatment of Chlamydia related diseases (including C. trachomatis, Chlamydia psittaci, Chlamydia pneumonia), Anti-malarial Agents as Dihydropteroate synthetase inhibitors, alternative drugs in tuberculosis treatment, long term treatment of leprosy, treatment of ocular infections. In the latter treatment causative organisms must be identified, and it is preferable to use a drug that is not given systemically. Sulfonamides are also assumed as permitted antibiotics in Pregnancy (Kayser et al., 2004).

In the title compund, (Fig. 1), bond lengths (Allen et al., 1987) and angles are within the normal ranges and are comparable with the related structures (Mehrabi et al., 2008; Ali et al. 2007). The molecule adopts a twisted E configuration around the C═N bond. The two outer phenyl rings twisted from each other making a dihedral angle of 78.00 (12)°. The methyl-substituted benzene ring makes dihedral angles of 32.37 (14) and 69.70 (12)° with the two outer benzene rings. In the crystal structure the molecule linked together into extended 1-D chains along the b axis through intermolecular N—H···O hydrogen bonds (Table 1, Fig. 2).

Related literature top

For related structures and bioactivities, see; for example, Mehrabi et al. (2008); Tabatabaee et al. (2007); Ali et al. (2007); Tierney et al. 2006; Krygowski et al. (1998); Kayser et al. (2004). For bond-length data, see: Allen et al. (1987).

Experimental top

The synthesis is the same as the earlier report (Mehrabi et al., 2008), except that penylcinnamaldehyde (3 mmol) was used. Single crystals suitable for X-ray analysis were obtained from ethanol solution at room temperature.

Computing details top

Data collection: X-AREA (Stoe & Cie, 2005); cell refinement: X-AREA (Stoe & Cie, 2005); data reduction: X-AREA (Stoe & Cie, 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, 2009).

Figures top

	Fig. 1. The molecular structure of the title compound, showing 30% probability displacement ellipsoids and the atomic numbering.
	Fig. 2. The crystal packing of the title compound, viewed down the a-axis, showing a 1-D extended chain along the b-axis. Intermolecular hydrogen bonds are shown as dashed lines.

(E)-N'-(3,3-Diphenylallylidene)-p-toluenesulfonohydrazide top

Crystal data top

C₂₂H₂₀N₂O₂S	F(000) = 792
M_r = 376.46	D_x = 1.238 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2500 reflections
a = 14.785 (3) Å	θ = 2.3–29.2°
b = 6.2179 (12) Å	µ = 0.18 mm⁻¹
c = 22.519 (5) Å	T = 294 K
β = 102.64 (3)°	Block, colourless
V = 2020.0 (7) Å³	0.50 × 0.28 × 0.12 mm
Z = 4

Data collection top

Stoe IPDS-II diffractometer	5327 independent reflections
Radiation source: fine-focus sealed tube	4220 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.000
Detector resolution: 0.15 pixels mm^-1	θ_max = 29.0°, θ_min = 1.9°
rotation method scans	h = −20→19
Absorption correction: numerical (X-RED32; Stoe & Cie, 2005)	k = 0→8
T_min = 0.940, T_max = 0.980	l = 0→30
5327 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)] = 0.057	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.156	H atoms treated by a mixture of independent and constrained refinement
S = 1.10	w = 1/[σ²(F_o²) + (0.0702P)² + 0.4245P] where P = (F_o² + 2F_c²)/3
5327 reflections	(Δ/σ)_max < 0.001
249 parameters	Δρ_max = 0.21 e Å⁻³
0 restraints	Δρ_min = −0.26 e Å⁻³

Crystal data top

C₂₂H₂₀N₂O₂S	V = 2020.0 (7) Å³
M_r = 376.46	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 14.785 (3) Å	µ = 0.18 mm⁻¹
b = 6.2179 (12) Å	T = 294 K
c = 22.519 (5) Å	0.50 × 0.28 × 0.12 mm
β = 102.64 (3)°

Data collection top

Stoe IPDS-II diffractometer	5327 independent reflections
Absorption correction: numerical (X-RED32; Stoe & Cie, 2005)	4220 reflections with I > 2σ(I)
T_min = 0.940, T_max = 0.980	R_int = 0.000
5327 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.057	0 restraints
wR(F²) = 0.156	H atoms treated by a mixture of independent and constrained refinement
S = 1.10	Δρ_max = 0.21 e Å⁻³
5327 reflections	Δρ_min = −0.26 e Å⁻³
249 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	0.36602 (3)	0.58739 (7)	0.24598 (2)	0.05559 (15)
O1	0.39657 (11)	0.7837 (2)	0.22433 (7)	0.0741 (4)
O2	0.30743 (11)	0.5917 (2)	0.28899 (6)	0.0719 (4)
N1	0.35283 (10)	0.4163 (2)	0.14209 (6)	0.0542 (3)
N2	0.30481 (11)	0.4572 (3)	0.18786 (7)	0.0544 (3)
H1N2	0.2757 (15)	0.355 (4)	0.1974 (10)	0.065 (6)*
C1	0.35959 (15)	−0.1126 (3)	−0.08028 (10)	0.0681 (5)
H1	0.3228	−0.2220	−0.0702	0.082*
C2	0.40308 (17)	−0.1410 (4)	−0.12878 (11)	0.0781 (6)
H2	0.3953	−0.2693	−0.1505	0.094*
C3	0.45712 (15)	0.0186 (4)	−0.14457 (9)	0.0722 (6)
H3	0.4856	−0.0004	−0.1772	0.087*
C4	0.46904 (15)	0.2069 (4)	−0.11195 (9)	0.0695 (5)
H4	0.5062	0.3152	−0.1223	0.083*
C5	0.42599 (14)	0.2365 (3)	−0.06367 (9)	0.0616 (4)
H5	0.4344	0.3652	−0.0421	0.074*
C6	0.37052 (12)	0.0769 (3)	−0.04690 (7)	0.0521 (4)
C7	0.32394 (12)	0.1032 (3)	0.00479 (7)	0.0512 (4)
C8	0.23773 (13)	−0.0247 (3)	0.00290 (8)	0.0544 (4)
C9	0.15991 (16)	0.0142 (4)	−0.04264 (10)	0.0781 (6)
H9	0.1624	0.1197	−0.0715	0.094*
C10	0.07956 (19)	−0.0983 (5)	−0.04624 (15)	0.0994 (9)
H10	0.0282	−0.0704	−0.0774	0.119*
C11	0.0753 (2)	−0.2508 (5)	−0.0041 (2)	0.1177 (12)
H11	0.0205	−0.3268	−0.0061	0.141*
C12	0.1509 (3)	−0.2946 (5)	0.04175 (19)	0.1156 (11)
H12	0.1473	−0.4006	0.0703	0.139*
C13	0.23312 (18)	−0.1804 (4)	0.04555 (13)	0.0834 (7)
H13	0.2844	−0.2092	0.0766	0.100*
C14	0.35757 (13)	0.2367 (3)	0.05125 (8)	0.0569 (4)
H14	0.4129	0.3070	0.0508	0.068*
C15	0.31479 (13)	0.2803 (3)	0.10200 (8)	0.0538 (4)
H15	0.2605	0.2104	0.1053	0.065*
C16	0.46334 (13)	0.4280 (3)	0.27515 (8)	0.0570 (4)
C17	0.55009 (15)	0.4897 (5)	0.26802 (10)	0.0759 (6)
H17	0.5581	0.6184	0.2488	0.091*
C18	0.62509 (18)	0.3562 (6)	0.29011 (12)	0.0933 (8)
H18	0.6837	0.3981	0.2858	0.112*
C19	0.6153 (2)	0.1648 (5)	0.31798 (13)	0.0914 (8)
C22	0.6986 (2)	0.0211 (6)	0.3407 (2)	0.1415 (16)
H22A	0.7542	0.0967	0.3381	0.212*
H22B	0.6932	−0.1064	0.3162	0.212*
H22C	0.7010	−0.0179	0.3823	0.212*
C20	0.5286 (2)	0.1072 (4)	0.32492 (14)	0.0966 (9)
H20	0.5210	−0.0213	0.3444	0.116*
C21	0.45251 (17)	0.2363 (4)	0.30362 (12)	0.0786 (6)
H21	0.3942	0.1942	0.3084	0.094*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0643 (3)	0.0552 (2)	0.0519 (2)	−0.00057 (19)	0.02298 (19)	−0.01132 (18)
O1	0.0889 (10)	0.0543 (7)	0.0837 (9)	−0.0098 (7)	0.0286 (8)	−0.0086 (7)
O2	0.0832 (9)	0.0781 (9)	0.0640 (8)	0.0105 (7)	0.0370 (7)	−0.0117 (7)
N1	0.0601 (8)	0.0606 (8)	0.0454 (7)	−0.0058 (7)	0.0190 (6)	−0.0035 (6)
N2	0.0594 (8)	0.0600 (9)	0.0480 (7)	−0.0072 (7)	0.0209 (6)	−0.0032 (6)
C1	0.0765 (13)	0.0665 (11)	0.0675 (11)	−0.0158 (10)	0.0293 (10)	−0.0145 (9)
C2	0.0904 (15)	0.0796 (14)	0.0729 (12)	−0.0118 (12)	0.0365 (11)	−0.0235 (11)
C3	0.0722 (12)	0.0916 (15)	0.0594 (10)	0.0002 (11)	0.0290 (9)	−0.0038 (11)
C4	0.0714 (12)	0.0818 (14)	0.0608 (10)	−0.0133 (10)	0.0265 (9)	0.0047 (10)
C5	0.0723 (11)	0.0609 (10)	0.0549 (9)	−0.0121 (9)	0.0208 (8)	−0.0040 (8)
C6	0.0554 (9)	0.0571 (9)	0.0451 (8)	−0.0038 (7)	0.0137 (7)	−0.0010 (7)
C7	0.0578 (9)	0.0527 (9)	0.0444 (7)	−0.0030 (7)	0.0141 (7)	0.0019 (7)
C8	0.0608 (10)	0.0531 (9)	0.0523 (8)	−0.0054 (8)	0.0191 (7)	−0.0029 (7)
C9	0.0677 (12)	0.0984 (16)	0.0666 (12)	−0.0119 (12)	0.0111 (10)	0.0101 (12)
C10	0.0685 (14)	0.119 (2)	0.107 (2)	−0.0174 (15)	0.0096 (14)	−0.0027 (18)
C11	0.0759 (18)	0.097 (2)	0.186 (4)	−0.0279 (16)	0.041 (2)	−0.009 (2)
C12	0.117 (2)	0.0794 (18)	0.161 (3)	−0.0208 (17)	0.053 (2)	0.0344 (19)
C13	0.0860 (15)	0.0677 (13)	0.0986 (17)	−0.0073 (12)	0.0246 (13)	0.0253 (12)
C14	0.0610 (10)	0.0638 (10)	0.0482 (8)	−0.0086 (8)	0.0173 (7)	−0.0043 (7)
C15	0.0587 (9)	0.0567 (9)	0.0482 (8)	−0.0067 (8)	0.0164 (7)	−0.0020 (7)
C16	0.0616 (10)	0.0639 (10)	0.0457 (8)	−0.0021 (8)	0.0125 (7)	−0.0168 (8)
C17	0.0684 (12)	0.0996 (16)	0.0632 (11)	−0.0024 (12)	0.0217 (10)	−0.0067 (11)
C18	0.0626 (13)	0.138 (3)	0.0785 (15)	0.0057 (15)	0.0146 (11)	−0.0242 (17)
C19	0.0841 (16)	0.0917 (18)	0.0844 (16)	0.0213 (14)	−0.0124 (13)	−0.0338 (14)
C22	0.106 (2)	0.132 (3)	0.160 (3)	0.047 (2)	−0.027 (2)	−0.040 (3)
C20	0.0978 (19)	0.0686 (14)	0.107 (2)	0.0050 (13)	−0.0122 (16)	−0.0069 (13)
C21	0.0753 (13)	0.0665 (13)	0.0893 (15)	−0.0043 (11)	0.0075 (11)	−0.0036 (11)

Geometric parameters (Å, º) top

S1—O1	1.4240 (15)	C10—C11	1.353 (5)
S1—O2	1.4341 (14)	C10—H10	0.9300
S1—N2	1.6336 (17)	C11—C12	1.372 (5)
S1—C16	1.752 (2)	C11—H11	0.9300
N1—C15	1.274 (2)	C12—C13	1.394 (4)
N1—N2	1.3969 (19)	C12—H12	0.9300
N2—H1N2	0.82 (2)	C13—H13	0.9300
C1—C6	1.388 (3)	C14—C15	1.448 (2)
C1—C2	1.395 (3)	C14—H14	0.9300
C1—H1	0.9300	C15—H15	0.9300
C2—C3	1.369 (3)	C16—C21	1.380 (3)
C2—H2	0.9300	C16—C17	1.381 (3)
C3—C4	1.373 (3)	C17—C18	1.387 (4)
C3—H3	0.9300	C17—H17	0.9300
C4—C5	1.387 (3)	C18—C19	1.368 (4)
C4—H4	0.9300	C18—H18	0.9300
C5—C6	1.391 (2)	C19—C20	1.373 (4)
C5—H5	0.9300	C19—C22	1.516 (4)
C6—C7	1.486 (2)	C22—H22A	0.9600
C7—C14	1.343 (2)	C22—H22B	0.9600
C7—C8	1.495 (2)	C22—H22C	0.9600
C8—C13	1.376 (3)	C20—C21	1.380 (4)
C8—C9	1.385 (3)	C20—H20	0.9300
C9—C10	1.366 (3)	C21—H21	0.9300
C9—H9	0.9300

O1—S1—O2	119.94 (9)	C10—C11—C12	120.8 (3)
O1—S1—N2	108.18 (9)	C10—C11—H11	119.6
O2—S1—N2	103.87 (9)	C12—C11—H11	119.6
O1—S1—C16	108.48 (10)	C11—C12—C13	120.0 (3)
O2—S1—C16	108.97 (9)	C11—C12—H12	120.0
N2—S1—C16	106.60 (8)	C13—C12—H12	120.0
C15—N1—N2	115.26 (15)	C8—C13—C12	119.4 (3)
N1—N2—S1	113.54 (12)	C8—C13—H13	120.3
N1—N2—H1N2	115.6 (15)	C12—C13—H13	120.3
S1—N2—H1N2	113.8 (15)	C7—C14—C15	125.42 (17)
C6—C1—C2	120.84 (19)	C7—C14—H14	117.3
C6—C1—H1	119.6	C15—C14—H14	117.3
C2—C1—H1	119.6	N1—C15—C14	118.83 (16)
C3—C2—C1	120.5 (2)	N1—C15—H15	120.6
C3—C2—H2	119.8	C14—C15—H15	120.6
C1—C2—H2	119.8	C21—C16—C17	120.0 (2)
C2—C3—C4	119.55 (18)	C21—C16—S1	119.57 (16)
C2—C3—H3	120.2	C17—C16—S1	120.44 (18)
C4—C3—H3	120.2	C16—C17—C18	118.8 (3)
C3—C4—C5	120.34 (19)	C16—C17—H17	120.6
C3—C4—H4	119.8	C18—C17—H17	120.6
C5—C4—H4	119.8	C19—C18—C17	121.9 (3)
C4—C5—C6	121.15 (18)	C19—C18—H18	119.0
C4—C5—H5	119.4	C17—C18—H18	119.0
C6—C5—H5	119.4	C18—C19—C20	118.3 (2)
C1—C6—C5	117.65 (16)	C18—C19—C22	120.6 (3)
C1—C6—C7	119.93 (16)	C20—C19—C22	121.1 (3)
C5—C6—C7	122.42 (16)	C19—C22—H22A	109.5
C14—C7—C6	121.50 (16)	C19—C22—H22B	109.5
C14—C7—C8	121.27 (15)	H22A—C22—H22B	109.5
C6—C7—C8	117.23 (14)	C19—C22—H22C	109.5
C13—C8—C9	118.7 (2)	H22A—C22—H22C	109.5
C13—C8—C7	121.79 (19)	H22B—C22—H22C	109.5
C9—C8—C7	119.53 (17)	C19—C20—C21	121.3 (3)
C10—C9—C8	121.7 (2)	C19—C20—H20	119.3
C10—C9—H9	119.2	C21—C20—H20	119.3
C8—C9—H9	119.2	C16—C21—C20	119.7 (2)
C11—C10—C9	119.4 (3)	C16—C21—H21	120.1
C11—C10—H10	120.3	C20—C21—H21	120.1
C9—C10—H10	120.3

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H1N2···O2ⁱ	0.82 (2)	2.11 (2)	2.927 (2)	173 (2)

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

Experimental details

Crystal data
Chemical formula	C₂₂H₂₀N₂O₂S
M_r	376.46
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	294
a, b, c (Å)	14.785 (3), 6.2179 (12), 22.519 (5)
β (°)	102.64 (3)
V (Å³)	2020.0 (7)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.18
Crystal size (mm)	0.50 × 0.28 × 0.12

Data collection
Diffractometer	Stoe IPDS-II diffractometer
Absorption correction	Numerical (X-RED32; Stoe & Cie, 2005)
T_min, T_max	0.940, 0.980
No. of measured, independent and observed [I > 2σ(I)] reflections	5327, 5327, 4220
R_int	0.000
(sin θ/λ)_max (Å⁻¹)	0.682

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.057, 0.156, 1.10
No. of reflections	5327
No. of parameters	249
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.21, −0.26

Computer programs: X-AREA (Stoe & Cie, 2005), 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
N2—H1N2···O2ⁱ	0.82 (2)	2.11 (2)	2.927 (2)	173 (2)

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

Footnotes

‡Additional corresponding author, e-mail: zsrkk@yahoo.com. Thomson Reuters ResearcherID: A-5471-2009.

Acknowledgements

HM thanks Vali-e-Asr University of Rafsanjan for the finacial support of this work. RK thanks Universiti Sains Malaysia for a post-doctoral research fellowship.

References

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