1-(6-Chloro-1-methyl-1H-imidazo[4,5-c]pyridin-4-yl)-3-(2-chloro­phen­yl)urea

Devaru, V.B.; Vinduvahini, M.; Madaiah, M.; Revanasiddappa, H.D.; Devarajegowda, H.C.

doi:10.1107/S1600536814000695

organic compounds

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ISSN: 2056-9890

Volume 70| Part 2| February 2014| Pages o155-o156

doi:10.1107/S1600536814000695

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1-(6-Chloro-1-methyl-1H-imidazo[4,5-c]pyridin-4-yl)-3-(2-chlorophenyl)urea

Venkatesh B. Devaru,^a M. Vinduvahini,^b M. Madaiah,^c H. D. Revanasiddappa ^c and H. C. Devarajegowda ^d ^*

^aP. G. Department of Physics, LVD College, Raichur 584 103, Karnataka, India, ^bDepartment of Physics, Sri D Devaraja Urs Govt. First Grade College, Hunsur 571 105, Mysore District, Karnataka, India, ^cDepartment of Studies in Chemistry, Manasagangotri, University of Mysore, Mysore 570 006, Karnataka, India, and ^dDepartment of Physics, Yuvaraja's College (Constituent College), University of Mysore, Mysore 570 005, Karnataka, India
^*Correspondence e-mail: devarajegowda@yahoo.com

(Received 8 January 2014; accepted 11 January 2014; online 18 January 2014)

In the title compound, C₁₄H₁₁Cl₂N₅O, the plane of the 1H-imidazo[4,5-c]pyridine ring system [r.m.s. deviation = 0.087 (19) Å] makes a dihedral angle of 4.87 (10)° with the terminal phenyl ring. An intramolecular N—H⋯N hydrogen bond stabilizes the molecular conformation. In the crystal, N—H⋯O hydrogen bonds link the molecules into inversion dimers. These dimers are connected by π–π interactions between imidazole rings [shortest centroid–centroid distance = 3.4443 (14) Å].

CCDC reference: 981048

Related literature

For biological applications of imidazopyridines, see: Cappelli et al. (2006 ); Weier et al. (1994 ); Barraclough et al. (1990 ); Bavetsias et al. (2007 ); Cooper et al. (1992 ); Temple et al. (1987 ); Janssens et al. (1985 ); Kulkarni & Newman (2007 ). For a related structure, see: Kandri Rodi et al. (2013 ).

Experimental

Crystal data

C₁₄H₁₁Cl₂N₅O
M_r = 336.18
Monoclinic, P 2₁ /c
a = 8.9368 (3) Å
b = 17.2369 (4) Å
c = 10.3805 (3) Å
β = 114.216 (4)°
V = 1458.33 (7) Å³
Z = 4
Mo Kα radiation
μ = 0.45 mm⁻¹
T = 293 K
0.24 × 0.20 × 0.12 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2007 ) T_min = 0.770, T_max = 1.000
11425 measured reflections
2576 independent reflections
2175 reflections with I > 2σ(I)
R_int = 0.023

Refinement

R[F² > 2σ(F²)] = 0.039
wR(F²) = 0.112
S = 1.06
2576 reflections
199 parameters
H-atom parameters constrained
Δρ_max = 0.38 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
N7—H7⋯O3ⁱ	0.86	2.07	2.862 (3)	153
N8—H8⋯N6	0.86	2.03	2.723 (2)	136
Symmetry code: (i) -x+1, -y, -z+2.

Data collection: SMART (Bruker, 2001 ); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ); software used to prepare material for publication: SHELXL97.

Supporting information

CCDC reference: 981048

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536814000695/bt6956sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536814000695/bt6956Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536814000695/bt6956Isup3.cml

checkCIF report

Comment top

The identification of chemotherapeutic targets could lead to new therapeutic approaches and may be a key for the discovery of really effective drugs. The imidazopyridine (Cappelli et al., 2006; Weier et al., 1994; Barraclough et al., 1990; Bavetsias et al., 2007) moieties are important pharmacophores, which have proven to be useful for a number of biologically relevant targets. The compounds derived from the imidazopyridine system have recently been evaluated as antagonists of various biological receptors, including angiotensin-II and platelet activating factor (Cooper et al., 1992). Substituted imidazo[4,5]pyridines have also been tested for their potential as anticancer (Temple et al., 1987) and selective antihistamine (H1) agents (Janssens et al., 1985). Imidazo[4,5]pyridine derivatives were also reported as inhibitors of Mitogen and stress-activated protein kinases and Aurora kinases (Kulkarni & Newman, 2007). The bond lengths and bond angles are good agreement with a related structure (Kandri Rodi et al., 2013)

The asymmetric unit of 1-(6-chloro-1-methyl-1H-imidazo [4,5-c]pyridin-4-yl)-3-(2-chlorophenyl)urea is shown in Fig. 1. The 1H-imidazo[4,5-c]pyridine ring (N4/N5/N6/C10–C15) system makes a dihedral angle of 4.87 (10)° with the terminal phenyl ring.

An intramolecular N-H···N hydrogen bond stabilizes the molecular conformation. Intermolecular N-H···O hydrogen bonds link the molecules to centrosymmetric dimers. These dimers are further connected by intermolecular π–π interactions between imidazole rings [shortest centroid–centroid distance = 3.4443 (14) Å]. A view of the crystal packing is given in Figure 2.

Related literature top

For biological applications of imidazopyridine, see: Cappelli et al. (2006); Weier et al. (1994); Barraclough et al. (1990); Bavetsias et al. (2007); Cooper et al. (1992); Temple et al. (1987); Janssens et al. (1985); Kulkarni & Newman (2007). For a related structure, see: Kandri Rodi et al. (2013).

Experimental top

A mixture of 2,4,6-trichloropyridene, methylamine in ethanol was heated and filtered to get pure product. To this sulfuric acid and fuming nitric acid was added, then it was stirred and cooled. A solution of iron powder and ammonium chloride in methanol/water was added and heated. Then triethylorthoformate in ethanol was added and continued the heating. Amination of reaction product was achieved by adding benzophenone imine, potassium carbonate, palladium complex, in dioxane, and then it was heated. The obtained product was dissolved in HCl, stirred, and concentrated in vacuo to give the product. A mixture of obtained product, sodium hydride, 6-chloro-1-methyl-1H-imidazol [4,5-c]pyridin-4-amine and carbonyl/sulfonyl chlorides in tetahydrofuran was stirred and concentrated in vacuo to give the expected products. After completion of each step of the reaction TLC was monitored. The compound is recrystallized by ethanol- chloroform mixture. Colourless needles of the title compound were grown from a mixed solution of Ethanol/Chloroform (V/V = 2/1) by slow evaporation at room temperature. Yield: 122 mg, 66.27%; m p: 380; IR cm-1 (KBr) 3431, 1669; Anal. Calcd for C₁₄H₁₁Cl₂N₅O C,50.02; H, 3.30; N, 20.83%; Found, C, 49.45; H, 3.25; N, 20.44%.

Structure description top

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound. Displacement ellipsoids are drawn at the 50% probability level. Hydrogen atoms are shown as spheres of arbitrary radius. Hydrogen bonds are shown as open dashed bonds.
	Fig. 2. The packing of the title compound. Intermolecular hydrogen bonds are shown as dashed lines.

1-(6-Chloro-1-methyl-1H-imidazo[4,5-c]pyridin-4-yl)-3-(2-chlorophenyl)urea top

Crystal data top

C₁₄H₁₁Cl₂N₅O	F(000) = 688
M_r = 336.18	D_x = 1.531 Mg m⁻³
Monoclinic, P2₁/c	Melting point: 380 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 8.9368 (3) Å	Cell parameters from 2576 reflections
b = 17.2369 (4) Å	θ = 2.4–25.0°
c = 10.3805 (3) Å	µ = 0.45 mm⁻¹
β = 114.216 (4)°	T = 293 K
V = 1458.33 (7) Å³	Plate, colourless
Z = 4	0.24 × 0.20 × 0.12 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	2576 independent reflections
Radiation source: fine-focus sealed tube	2175 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.023
ω and φ scans	θ_max = 25.0°, θ_min = 2.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 2007)	h = −10→10
T_min = 0.770, T_max = 1.000	k = −20→20
11425 measured reflections	l = −12→12

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.112	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.0553P)² + 0.5893P] where P = (F_o² + 2F_c²)/3
2576 reflections	(Δ/σ)_max = 0.001
199 parameters	Δρ_max = 0.38 e Å⁻³
0 restraints	Δρ_min = −0.28 e Å⁻³

Crystal data top

C₁₄H₁₁Cl₂N₅O	V = 1458.33 (7) Å³
M_r = 336.18	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 8.9368 (3) Å	µ = 0.45 mm⁻¹
b = 17.2369 (4) Å	T = 293 K
c = 10.3805 (3) Å	0.24 × 0.20 × 0.12 mm
β = 114.216 (4)°

Data collection top

Bruker SMART CCD area-detector diffractometer	2576 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2007)	2175 reflections with I > 2σ(I)
T_min = 0.770, T_max = 1.000	R_int = 0.023
11425 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.039	0 restraints
wR(F²) = 0.112	H-atom parameters constrained
S = 1.06	Δρ_max = 0.38 e Å⁻³
2576 reflections	Δρ_min = −0.28 e Å⁻³
199 parameters

Special details top

Experimental. IR cm-1 (KBr) 3431, 1669; Anal. Calcd for C₁₄H₁₁Cl₂N₅O C,50.02; H, 3.30; N, 20.83%; Found, C, 49.45; H, 3.25; N, 20.44%.

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	0.98140 (8)	0.21079 (4)	0.85698 (7)	0.0611 (2)
Cl2	1.28185 (8)	0.14285 (4)	1.18265 (7)	0.0693 (2)
O3	0.50876 (19)	0.04206 (11)	0.86633 (16)	0.0599 (5)
N4	1.1433 (2)	−0.06979 (11)	1.47101 (19)	0.0457 (5)
N5	0.8783 (2)	−0.07679 (11)	1.31848 (19)	0.0474 (5)
N6	1.0050 (2)	0.07252 (10)	1.12745 (18)	0.0424 (4)
N7	0.7418 (2)	0.01864 (11)	1.05733 (18)	0.0447 (5)
H7	0.6847	−0.0136	1.0818	0.054*
N8	0.7379 (2)	0.10758 (10)	0.88673 (17)	0.0389 (4)
H8	0.8420	0.1107	0.9357	0.047*
C9	1.2941 (3)	−0.08685 (16)	1.5946 (2)	0.0587 (6)
H9A	1.3816	−0.0553	1.5925	0.088*
H9B	1.3215	−0.1406	1.5937	0.088*
H9C	1.2783	−0.0758	1.6789	0.088*
C10	0.9933 (3)	−0.10224 (14)	1.4362 (2)	0.0502 (6)
H10	0.9738	−0.1398	1.4919	0.060*
C11	0.9608 (3)	−0.02290 (12)	1.2725 (2)	0.0386 (5)
C12	0.9041 (2)	0.02356 (12)	1.1512 (2)	0.0379 (5)
C13	1.1616 (3)	0.07603 (13)	1.2225 (2)	0.0451 (5)
C14	1.2320 (3)	0.03333 (13)	1.3434 (2)	0.0461 (5)
H14	1.3418	0.0380	1.4053	0.055*
C15	1.1242 (3)	−0.01774 (12)	1.3656 (2)	0.0397 (5)
C16	0.6546 (3)	0.05620 (13)	0.9311 (2)	0.0408 (5)
C17	0.6706 (3)	0.15605 (11)	0.7687 (2)	0.0389 (5)
C18	0.5051 (3)	0.15738 (14)	0.6761 (2)	0.0472 (5)
H18	0.4318	0.1235	0.6897	0.057*
C19	0.4496 (3)	0.20893 (14)	0.5640 (3)	0.0545 (6)
H19	0.3389	0.2093	0.5032	0.065*
C20	0.5541 (4)	0.25923 (15)	0.5406 (3)	0.0621 (7)
H20	0.5148	0.2933	0.4646	0.075*
C21	0.7172 (4)	0.25902 (14)	0.6304 (3)	0.0599 (7)
H21	0.7893	0.2929	0.6152	0.072*
C22	0.7742 (3)	0.20852 (12)	0.7430 (2)	0.0444 (5)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0526 (4)	0.0597 (4)	0.0696 (4)	−0.0158 (3)	0.0237 (3)	−0.0005 (3)
Cl2	0.0440 (4)	0.0822 (5)	0.0688 (4)	−0.0224 (3)	0.0101 (3)	0.0153 (3)
O3	0.0347 (9)	0.0818 (12)	0.0484 (9)	−0.0163 (8)	0.0022 (7)	0.0204 (8)
N4	0.0397 (10)	0.0505 (11)	0.0404 (10)	0.0087 (8)	0.0100 (8)	0.0054 (8)
N5	0.0400 (10)	0.0526 (11)	0.0467 (11)	0.0006 (9)	0.0147 (9)	0.0106 (9)
N6	0.0363 (10)	0.0455 (10)	0.0408 (10)	−0.0063 (8)	0.0112 (8)	−0.0004 (8)
N7	0.0341 (10)	0.0529 (11)	0.0387 (10)	−0.0093 (8)	0.0065 (8)	0.0110 (8)
N8	0.0336 (9)	0.0449 (10)	0.0351 (9)	−0.0055 (8)	0.0111 (7)	0.0019 (8)
C9	0.0453 (14)	0.0688 (16)	0.0477 (14)	0.0113 (12)	0.0047 (11)	0.0098 (12)
C10	0.0472 (13)	0.0525 (13)	0.0499 (13)	0.0054 (11)	0.0188 (11)	0.0130 (11)
C11	0.0343 (11)	0.0416 (11)	0.0379 (11)	0.0012 (9)	0.0126 (9)	0.0003 (9)
C12	0.0327 (11)	0.0422 (11)	0.0362 (11)	−0.0005 (9)	0.0114 (9)	−0.0016 (9)
C13	0.0357 (11)	0.0494 (13)	0.0465 (12)	−0.0066 (10)	0.0131 (10)	−0.0024 (10)
C14	0.0315 (11)	0.0536 (13)	0.0450 (12)	−0.0006 (10)	0.0074 (10)	−0.0022 (10)
C15	0.0378 (11)	0.0415 (11)	0.0365 (11)	0.0041 (9)	0.0119 (9)	−0.0026 (9)
C16	0.0363 (12)	0.0457 (12)	0.0363 (11)	−0.0043 (9)	0.0108 (9)	0.0019 (9)
C17	0.0470 (12)	0.0365 (11)	0.0353 (10)	−0.0009 (9)	0.0191 (10)	−0.0032 (9)
C18	0.0472 (13)	0.0524 (13)	0.0402 (12)	−0.0004 (11)	0.0162 (10)	0.0034 (10)
C19	0.0591 (15)	0.0563 (15)	0.0422 (13)	0.0083 (12)	0.0146 (12)	0.0050 (11)
C20	0.084 (2)	0.0523 (14)	0.0493 (14)	0.0061 (14)	0.0261 (14)	0.0143 (12)
C21	0.0801 (19)	0.0470 (14)	0.0592 (16)	−0.0078 (13)	0.0351 (15)	0.0056 (12)
C22	0.0544 (14)	0.0394 (11)	0.0433 (12)	−0.0050 (10)	0.0239 (11)	−0.0041 (9)

Geometric parameters (Å, º) top

Cl1—C22	1.741 (2)	C9—H9C	0.9600
Cl2—C13	1.737 (2)	C10—H10	0.9300
O3—C16	1.221 (2)	C11—C15	1.384 (3)
N4—C10	1.357 (3)	C11—C12	1.399 (3)
N4—C15	1.371 (3)	C13—C14	1.366 (3)
N4—C9	1.460 (3)	C14—C15	1.391 (3)
N5—C10	1.309 (3)	C14—H14	0.9300
N5—C11	1.387 (3)	C17—C18	1.395 (3)
N6—C12	1.330 (3)	C17—C22	1.396 (3)
N6—C13	1.343 (3)	C18—C19	1.384 (3)
N7—C12	1.379 (3)	C18—H18	0.9300
N7—C16	1.381 (3)	C19—C20	1.366 (4)
N7—H7	0.8600	C19—H19	0.9300
N8—C16	1.353 (3)	C20—C21	1.371 (4)
N8—C17	1.399 (3)	C20—H20	0.9300
N8—H8	0.8600	C21—C22	1.377 (3)
C9—H9A	0.9600	C21—H21	0.9300
C9—H9B	0.9600

C10—N4—C15	105.76 (18)	C14—C13—Cl2	118.66 (17)
C10—N4—C9	127.3 (2)	C13—C14—C15	113.8 (2)
C15—N4—C9	127.0 (2)	C13—C14—H14	123.1
C10—N5—C11	102.76 (18)	C15—C14—H14	123.1
C12—N6—C13	118.28 (18)	N4—C15—C11	105.38 (18)
C12—N7—C16	131.50 (18)	N4—C15—C14	132.7 (2)
C12—N7—H7	114.3	C11—C15—C14	121.92 (19)
C16—N7—H7	114.3	O3—C16—N8	123.74 (19)
C16—N8—C17	126.16 (18)	O3—C16—N7	119.21 (19)
C16—N8—H8	116.9	N8—C16—N7	117.06 (18)
C17—N8—H8	116.9	C18—C17—C22	117.2 (2)
N4—C9—H9A	109.5	C18—C17—N8	124.54 (19)
N4—C9—H9B	109.5	C22—C17—N8	118.3 (2)
H9A—C9—H9B	109.5	C19—C18—C17	120.2 (2)
N4—C9—H9C	109.5	C19—C18—H18	119.9
H9A—C9—H9C	109.5	C17—C18—H18	119.9
H9B—C9—H9C	109.5	C20—C19—C18	121.4 (3)
N5—C10—N4	115.0 (2)	C20—C19—H19	119.3
N5—C10—H10	122.5	C18—C19—H19	119.3
N4—C10—H10	122.5	C19—C20—C21	119.4 (2)
C15—C11—N5	111.13 (18)	C19—C20—H20	120.3
C15—C11—C12	118.69 (19)	C21—C20—H20	120.3
N5—C11—C12	130.18 (19)	C20—C21—C22	119.9 (2)
N6—C12—N7	120.29 (18)	C20—C21—H21	120.0
N6—C12—C11	120.47 (19)	C22—C21—H21	120.0
N7—C12—C11	119.24 (18)	C21—C22—C17	121.9 (2)
N6—C13—C14	126.8 (2)	C21—C22—Cl1	118.86 (18)
N6—C13—Cl2	114.53 (16)	C17—C22—Cl1	119.23 (17)

C11—N5—C10—N4	0.0 (3)	C12—C11—C15—N4	−179.29 (18)
C15—N4—C10—N5	0.2 (3)	N5—C11—C15—C14	−179.01 (19)
C9—N4—C10—N5	−179.6 (2)	C12—C11—C15—C14	1.4 (3)
C10—N5—C11—C15	−0.2 (2)	C13—C14—C15—N4	−179.8 (2)
C10—N5—C11—C12	179.3 (2)	C13—C14—C15—C11	−0.7 (3)
C13—N6—C12—N7	179.27 (19)	C17—N8—C16—O3	5.1 (3)
C13—N6—C12—C11	0.0 (3)	C17—N8—C16—N7	−174.47 (18)
C16—N7—C12—N6	1.5 (4)	C12—N7—C16—O3	−179.5 (2)
C16—N7—C12—C11	−179.2 (2)	C12—N7—C16—N8	0.1 (4)
C15—C11—C12—N6	−1.1 (3)	C16—N8—C17—C18	−1.4 (3)
N5—C11—C12—N6	179.5 (2)	C16—N8—C17—C22	176.71 (19)
C15—C11—C12—N7	179.66 (19)	C22—C17—C18—C19	0.3 (3)
N5—C11—C12—N7	0.2 (3)	N8—C17—C18—C19	178.4 (2)
C12—N6—C13—C14	0.8 (4)	C17—C18—C19—C20	0.2 (4)
C12—N6—C13—Cl2	−179.04 (15)	C18—C19—C20—C21	−0.3 (4)
N6—C13—C14—C15	−0.5 (3)	C19—C20—C21—C22	−0.2 (4)
Cl2—C13—C14—C15	179.40 (16)	C20—C21—C22—C17	0.8 (4)
C10—N4—C15—C11	−0.3 (2)	C20—C21—C22—Cl1	−178.9 (2)
C9—N4—C15—C11	179.5 (2)	C18—C17—C22—C21	−0.8 (3)
C10—N4—C15—C14	178.9 (2)	N8—C17—C22—C21	−179.0 (2)
C9—N4—C15—C14	−1.3 (4)	C18—C17—C22—Cl1	178.84 (16)
N5—C11—C15—N4	0.3 (2)	N8—C17—C22—Cl1	0.6 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N7—H7···O3ⁱ	0.86	2.07	2.862 (3)	153
N8—H8···N6	0.86	2.03	2.723 (2)	136

Symmetry code: (i) −x+1, −y, −z+2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N7—H7···O3ⁱ	0.86	2.0700	2.862 (3)	153
N8—H8···N6	0.86	2.0300	2.723 (2)	136

Symmetry code: (i) −x+1, −y, −z+2.

Acknowledgements

VBD acknowledges the VGST (Vision Group of Science & Technology, Department. IT, BT and S & T, Govt. of Karnataka) for financial support (No. VGST/P-15/K-FIST Level-1 /2010–11/744 dated 21/03/2011).

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