4-{(E)-[2-(Pyridin-3-ylcarbon­yl)hydrazinyl­idene]meth­yl}phenyl acetate

Datta, R.; Ramya, V.; Sithambaresan, M.; Kurup, M.R.P.

doi:10.1107/S1600536813025075

organic compounds

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Volume 69| Part 10| October 2013| Page o1549

doi:10.1107/S1600536813025075

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4-{(E)-[2-(Pyridin-3-ylcarbonyl)hydrazinylidene]methyl}phenyl acetate

Riya Datta,^a V. Ramya,^a M. Sithambaresan ^b ^* and M. R. Prathapachandra Kurup ^c

^aDepartment of Chemistry, Christ University, Hosur Road, Bangalore 560 029, India, ^bDepartment of Chemistry, Faculty of Science, Eastern University, Sri Lanka, Chenkalady, Sri Lanka, and ^cDepartment of Applied Chemistry, Cochin University of Science and Technology, Kochi 682 022, India
^*Correspondence e-mail: eesans@yahoo.com

(Received 25 August 2013; accepted 9 September 2013; online 18 September 2013)

The title compound, C₁₅H₁₃N₃O₃, exists in the E conformation with respect to the azomethane C=N double bond. The pyridyl and phenyl rings form dihedral angles of 35.67 (8) and 36.65 (7)°, respectively with the central C(=O)N₂C unit. In the crystal, N—H⋯O and C—H⋯O hydrogen bonds connect the molecules into chains along the b axis. Another C—H⋯O interaction connects molecules along the c-axis direction, forming layers.

CCDC reference: 960153

Related literature

For biological applications of benzohydrazones and their derivatives, see: Sreeja et al. (2004 ); Rakha et al. (1996 ); Takahama (1996 ). For the synthesis of related compounds, see: Emmanuel et al. (2011 ). For related structures, see: Reshma et al. (2012 ).

Experimental

Crystal data

C₁₅H₁₃N₃O₃
M_r = 283.28
Monoclinic, P 2₁ /n
a = 16.347 (4) Å
b = 5.0859 (10) Å
c = 18.408 (5) Å
β = 115.311 (9)°
V = 1383.6 (6) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 296 K
0.50 × 0.30 × 0.25 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2004 ) T_min = 0.953, T_max = 0.976
9585 measured reflections
3325 independent reflections
2288 reflections with I > 2σ(I)
R_int = 0.023

Refinement

R[F² > 2σ(F²)] = 0.049
wR(F²) = 0.140
S = 1.04
3325 reflections
195 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.31 e Å⁻³
Δρ_min = −0.25 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2′⋯O1ⁱ	0.87 (1)	2.08 (1)	2.9107 (18)	162 (2)
C7—H7⋯O1ⁱ	0.93	2.48	3.251 (2)	140
C15—H15C⋯O3ⁱⁱ	0.96	2.55	3.469 (4)	161
Symmetry codes: (i) x, y+1, z; (ii) -x+1, -y, -z+1.

Data collection: APEX2 (Bruker, 2004); cell refinement: APEX2 and SAINT (Bruker, 2004); data reduction: SAINT and XPREP (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 2012 ) and DIAMOND (Brandenburg, 2010 ); software used to prepare material for publication: SHELXL97 and publCIF (Westrip, 2010 ).

Supporting information

CCDC reference: 960153

Crystal structure: contains datablocks Global, I. DOI: 10.1107/S1600536813025075/fj2641sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813025075/fj2641Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536813025075/fj2641Isup3.cml

checkCIF report

Comment top

Hydrazone derivatives show excellent spectrum of biological activities (Sreeja et al., 2004). The chemical and pharmacological properties of aroylhydrazones have been extensively investigated recently owing to their potential application as antineoplastic, antiviral and antiinflammatory agents (Rakha et al., 1996; Takahama, 1996).

The compound (Fig. 1) crystallizes in the monoclinic space group P2₁/n. This molecule adopts an E configuration with respect to the C7=N3 bond and it exists in the amido form with a C6=O1 bond length of 1.2277 (18) Å which is very close to the reported C=O bond length of a related structure (Reshma et al., 2012). The O1 and N2 atoms are in a Z configuration with respect to C6–N2 having a torsion angle of 9.9 (3)°. The central C(=O)N₂C unit has dihedral angles of 35.67 (8) and 36.65 (7)°, respectively with the pyridyl and the phenyl rings.

There is a classical intermolecular N–H···O hydrogen bond interaction between the H atom attached at the N2 and O1 atom of neighbouring molecule with D···A distance of 2.9107 (18) Å and two C–H···O hydrogen bond interactions (Fig. 2) between the H atoms attached at the C7 & C15 and O1 & O3 atoms of neighbouring molecules with D···A distances of 3.251 (2) and 3.469 (4) Å, respectively. The classical hydrogen bond together with C–H···O interaction connect the molecules along b axis while the other C–H···O interaction chain the molecules along c axis in the crystal system. Four types of C–H···π interactions are also found in the molecular system (Fig. 3) with H···Cg distances of 3.1267, 3.2825, 3.3911 and 3.1984 Å forming a three-dimensional-supramolecuar architecture together with the intermolecular hydrogen bonding interactions. Although there are very weak short ring interactions found in the crystal system, they are not significant to support the network since centroid-centroid distances are above 4 Å. Fig. 4 shows a packing diagram of the title compound viewed along the b axis.

Related literature top

For biological applications of benzohydrazones and their derivatives, see: Sreeja et al. (2004); Rakha et al. (1996); Takahama (1996). For the synthesis of related compounds, see: Emmanuel et al. (2011). For related structures, see: Reshma et al. (2012).

Experimental top

The title compound was prepared by adapting a reported procedure (Emmanuel et al., 2011). A solution of pyridine-3-carbohydrazide (0.137 g, 1 mmol) in ethanol (10 ml) was mixed with a methanolic solution (10 ml) of 4-formylphenyl acetate (0.164 g, 1 mmol). The mixture was refluxed for 6 h after adding few drops of glacial acetic acid and then cooled to room temperature. The formed crystals were collected, washed with few drops of methanol and dried over P₄O₁₀ in vacuo. Colorless block shaped crystals, suitable for SXRD studies, were obtained after slow evaporation of the solution in air for a few days.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: APEX2 and SAINT (Bruker, 2004); data reduction: SAINT and XPREP (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 2012) and DIAMOND (Brandenburg, 2010); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and publCIF (Westrip, 2010).

Figures top

	Fig. 1. ORTEP view of the title compound drawn with 50% probability displacement ellipsoids for the non-H atoms.
	Fig. 2. Hydrogen-bonding interactions in the crystal structure of C₁₅H₁₃N₃O₃.
	Fig. 3. π···π interactions in the crystal structure of C₁₅H₁₃N₃O₃.
	Fig. 4. Packing diagram of the compound along the b axis.

4-{(E)-[2-(Pyridin-3-ylcarbonyl)hydrazinylidene]methyl}phenyl acetate top

Crystal data top

C₁₅H₁₃N₃O₃	F(000) = 592
M_r = 283.28	D_x = 1.360 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2983 reflections
a = 16.347 (4) Å	θ = 2.8–26.9°
b = 5.0859 (10) Å	µ = 0.10 mm⁻¹
c = 18.408 (5) Å	T = 296 K
β = 115.311 (9)°	Block, colorless
V = 1383.6 (6) Å³	0.50 × 0.30 × 0.25 mm
Z = 4

Data collection top

Bruker Kappa APEXII CCD diffractometer	3325 independent reflections
Radiation source: fine-focus sealed tube	2288 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.023
Detector resolution: 8.33 pixels mm^-1	θ_max = 28.0°, θ_min = 2.2°
ω and ϕ scan	h = −21→19
Absorption correction: multi-scan (SADABS; Bruker, 2004)	k = −6→6
T_min = 0.953, T_max = 0.976	l = −23→24
9585 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)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.140	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ²(F_o²) + (0.0632P)² + 0.3098P] where P = (F_o² + 2F_c²)/3
3325 reflections	(Δ/σ)_max < 0.001
195 parameters	Δρ_max = 0.31 e Å⁻³
1 restraint	Δρ_min = −0.25 e Å⁻³

Crystal data top

C₁₅H₁₃N₃O₃	V = 1383.6 (6) Å³
M_r = 283.28	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 16.347 (4) Å	µ = 0.10 mm⁻¹
b = 5.0859 (10) Å	T = 296 K
c = 18.408 (5) Å	0.50 × 0.30 × 0.25 mm
β = 115.311 (9)°

Data collection top

Bruker Kappa APEXII CCD diffractometer	3325 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2004)	2288 reflections with I > 2σ(I)
T_min = 0.953, T_max = 0.976	R_int = 0.023
9585 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.049	1 restraint
wR(F²) = 0.140	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	Δρ_max = 0.31 e Å⁻³
3325 reflections	Δρ_min = −0.25 e Å⁻³
195 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
O1	0.62319 (9)	−0.2235 (2)	−0.00860 (7)	0.0554 (4)
O2	0.64307 (10)	0.4099 (3)	0.44141 (7)	0.0639 (4)
N1	0.72016 (12)	0.3431 (3)	−0.15907 (10)	0.0597 (4)
N2	0.62677 (10)	0.2123 (3)	0.01908 (8)	0.0427 (3)
N3	0.62691 (10)	0.1739 (3)	0.09359 (8)	0.0420 (3)
C1	0.70076 (13)	0.2839 (3)	−0.09748 (10)	0.0477 (4)
H1	0.7253	0.3894	−0.0519	0.057*
C2	0.68290 (15)	0.1905 (4)	−0.22385 (11)	0.0603 (5)
H2	0.6949	0.2292	−0.2677	0.072*
C3	0.62814 (14)	−0.0194 (4)	−0.22982 (11)	0.0596 (5)
H3	0.6035	−0.1191	−0.2766	0.071*
C4	0.61008 (12)	−0.0806 (4)	−0.16510 (10)	0.0493 (4)
H4	0.5741	−0.2244	−0.1671	0.059*
C5	0.64659 (11)	0.0761 (3)	−0.09706 (9)	0.0365 (4)
C6	0.63100 (11)	0.0061 (3)	−0.02519 (10)	0.0380 (4)
C7	0.60960 (11)	0.3795 (3)	0.12422 (10)	0.0403 (4)
H7	0.5928	0.5334	0.0942	0.048*
C8	0.61583 (10)	0.3768 (3)	0.20592 (9)	0.0373 (4)
C9	0.66527 (12)	0.1856 (3)	0.26163 (10)	0.0457 (4)
H9	0.6934	0.0516	0.2464	0.055*
C10	0.67294 (12)	0.1932 (4)	0.33914 (10)	0.0510 (4)
H10	0.7064	0.0660	0.3762	0.061*
C11	0.63065 (12)	0.3906 (4)	0.36095 (10)	0.0477 (4)
C12	0.58098 (13)	0.5817 (4)	0.30759 (12)	0.0537 (5)
H12	0.5522	0.7130	0.3232	0.064*
C13	0.57459 (13)	0.5752 (3)	0.23019 (11)	0.0485 (4)
H13	0.5422	0.7056	0.1939	0.058*
C14	0.59039 (13)	0.2668 (4)	0.46456 (11)	0.0568 (5)
C15	0.61036 (14)	0.3114 (5)	0.55032 (11)	0.0647 (6)
H15A	0.6115	0.4968	0.5605	0.097*
H15B	0.6681	0.2362	0.5840	0.097*
H15C	0.5643	0.2299	0.5619	0.097*
H2'	0.6234 (12)	0.369 (2)	−0.0002 (10)	0.048 (5)*
O3	0.53569 (15)	0.1229 (5)	0.41928 (11)	0.1332 (10)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0910 (10)	0.0271 (6)	0.0590 (8)	−0.0011 (6)	0.0423 (7)	0.0038 (5)
O2	0.0756 (9)	0.0812 (10)	0.0411 (7)	−0.0283 (8)	0.0308 (7)	−0.0160 (7)
N1	0.0870 (12)	0.0523 (9)	0.0551 (9)	−0.0080 (8)	0.0450 (9)	0.0004 (8)
N2	0.0680 (9)	0.0283 (7)	0.0422 (8)	0.0018 (6)	0.0335 (7)	0.0051 (6)
N3	0.0589 (9)	0.0354 (7)	0.0401 (7)	−0.0009 (6)	0.0292 (6)	0.0034 (6)
C1	0.0674 (11)	0.0391 (9)	0.0435 (9)	−0.0065 (8)	0.0304 (9)	−0.0046 (7)
C2	0.0835 (14)	0.0644 (12)	0.0435 (10)	0.0063 (11)	0.0373 (10)	0.0064 (9)
C3	0.0724 (13)	0.0663 (13)	0.0356 (9)	0.0018 (10)	0.0189 (9)	−0.0102 (9)
C4	0.0540 (10)	0.0445 (9)	0.0458 (10)	−0.0027 (8)	0.0180 (8)	−0.0067 (8)
C5	0.0452 (8)	0.0296 (7)	0.0353 (8)	0.0060 (6)	0.0178 (7)	0.0034 (6)
C6	0.0484 (9)	0.0280 (8)	0.0399 (8)	0.0014 (6)	0.0209 (7)	0.0037 (6)
C7	0.0502 (9)	0.0336 (8)	0.0426 (9)	−0.0010 (7)	0.0252 (7)	0.0053 (7)
C8	0.0429 (8)	0.0349 (8)	0.0403 (8)	−0.0055 (6)	0.0237 (7)	−0.0007 (6)
C9	0.0494 (9)	0.0449 (9)	0.0471 (10)	0.0039 (7)	0.0248 (8)	0.0017 (8)
C10	0.0560 (10)	0.0550 (11)	0.0404 (9)	0.0027 (8)	0.0190 (8)	0.0061 (8)
C11	0.0543 (10)	0.0549 (11)	0.0384 (9)	−0.0167 (8)	0.0240 (8)	−0.0100 (8)
C12	0.0691 (12)	0.0469 (10)	0.0570 (11)	−0.0012 (9)	0.0384 (10)	−0.0091 (9)
C13	0.0602 (11)	0.0388 (9)	0.0513 (10)	0.0034 (8)	0.0285 (8)	0.0018 (8)
C14	0.0563 (11)	0.0758 (13)	0.0406 (9)	−0.0116 (10)	0.0230 (8)	−0.0064 (9)
C15	0.0679 (13)	0.0904 (16)	0.0411 (10)	−0.0038 (11)	0.0282 (9)	−0.0026 (10)
O3	0.1493 (18)	0.203 (2)	0.0656 (11)	−0.1225 (18)	0.0636 (12)	−0.0513 (13)

Geometric parameters (Å, º) top

O1—C6	1.2277 (18)	C7—C8	1.463 (2)
O2—C14	1.329 (2)	C7—H7	0.9300
O2—C11	1.410 (2)	C8—C13	1.389 (2)
N1—C2	1.332 (3)	C8—C9	1.394 (2)
N1—C1	1.336 (2)	C9—C10	1.378 (2)
N2—C6	1.348 (2)	C9—H9	0.9300
N2—N3	1.3844 (19)	C10—C11	1.373 (3)
N2—H2'	0.866 (9)	C10—H10	0.9300
N3—C7	1.276 (2)	C11—C12	1.374 (3)
C1—C5	1.381 (2)	C12—C13	1.384 (3)
C1—H1	0.9300	C12—H12	0.9300
C2—C3	1.367 (3)	C13—H13	0.9300
C2—H2	0.9300	C14—O3	1.180 (2)
C3—C4	1.380 (3)	C14—C15	1.486 (3)
C3—H3	0.9300	C15—H15A	0.9600
C4—C5	1.386 (2)	C15—H15B	0.9600
C4—H4	0.9300	C15—H15C	0.9600
C5—C6	1.493 (2)

C14—O2—C11	118.47 (14)	C13—C8—C9	118.60 (16)
C2—N1—C1	116.41 (17)	C13—C8—C7	119.60 (15)
C6—N2—N3	120.70 (13)	C9—C8—C7	121.75 (15)
C6—N2—H2'	118.8 (12)	C10—C9—C8	120.64 (16)
N3—N2—H2'	120.5 (12)	C10—C9—H9	119.7
C7—N3—N2	114.55 (13)	C8—C9—H9	119.7
N1—C1—C5	124.26 (16)	C11—C10—C9	119.27 (17)
N1—C1—H1	117.9	C11—C10—H10	120.4
C5—C1—H1	117.9	C9—C10—H10	120.4
N1—C2—C3	124.06 (18)	C10—C11—C12	121.74 (16)
N1—C2—H2	118.0	C10—C11—O2	119.60 (17)
C3—C2—H2	118.0	C12—C11—O2	118.53 (17)
C2—C3—C4	118.76 (17)	C11—C12—C13	118.72 (17)
C2—C3—H3	120.6	C11—C12—H12	120.6
C4—C3—H3	120.6	C13—C12—H12	120.6
C3—C4—C5	118.82 (18)	C12—C13—C8	121.02 (17)
C3—C4—H4	120.6	C12—C13—H13	119.5
C5—C4—H4	120.6	C8—C13—H13	119.5
C1—C5—C4	117.67 (16)	O3—C14—O2	120.82 (18)
C1—C5—C6	122.69 (14)	O3—C14—C15	126.92 (19)
C4—C5—C6	119.53 (15)	O2—C14—C15	112.26 (17)
O1—C6—N2	123.50 (15)	C14—C15—H15A	109.5
O1—C6—C5	121.50 (14)	C14—C15—H15B	109.5
N2—C6—C5	115.00 (13)	H15A—C15—H15B	109.5
N3—C7—C8	121.05 (14)	C14—C15—H15C	109.5
N3—C7—H7	119.5	H15A—C15—H15C	109.5
C8—C7—H7	119.5	H15B—C15—H15C	109.5

C6—N2—N3—C7	−170.37 (15)	N3—C7—C8—C13	−163.02 (16)
C2—N1—C1—C5	0.9 (3)	N3—C7—C8—C9	19.6 (2)
C1—N1—C2—C3	−0.7 (3)	C13—C8—C9—C10	0.1 (2)
N1—C2—C3—C4	−0.4 (3)	C7—C8—C9—C10	177.51 (15)
C2—C3—C4—C5	1.3 (3)	C8—C9—C10—C11	0.5 (3)
N1—C1—C5—C4	0.0 (3)	C9—C10—C11—C12	−0.2 (3)
N1—C1—C5—C6	176.14 (16)	C9—C10—C11—O2	−175.82 (15)
C3—C4—C5—C1	−1.1 (2)	C14—O2—C11—C10	−85.1 (2)
C3—C4—C5—C6	−177.41 (16)	C14—O2—C11—C12	99.2 (2)
N3—N2—C6—O1	9.9 (3)	C10—C11—C12—C13	−0.7 (3)
N3—N2—C6—C5	−169.77 (13)	O2—C11—C12—C13	174.95 (16)
C1—C5—C6—O1	−144.25 (18)	C11—C12—C13—C8	1.3 (3)
C4—C5—C6—O1	31.8 (2)	C9—C8—C13—C12	−1.0 (3)
C1—C5—C6—N2	35.5 (2)	C7—C8—C13—C12	−178.50 (16)
C4—C5—C6—N2	−148.44 (16)	C11—O2—C14—O3	1.5 (3)
N2—N3—C7—C8	−174.03 (14)	C11—O2—C14—C15	−179.02 (17)

Hydrogen-bond geometry (Å, º) top

Cg1and Cg2 are the centroids of the C8–C13 and C1–C5/N1 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2′···O1ⁱ	0.87 (1)	2.08 (1)	2.9107 (18)	162 (2)
C7—H7···O1ⁱ	0.93	2.48	3.251 (2)	140
C15—H15C···O3ⁱⁱ	0.96	2.55	3.469 (4)	161
C4—H4···Cg1ⁱⁱⁱ	0.93	3.13	3.821 (2)	133
C13—H13···Cg2ⁱⁱⁱ	0.93	3.28	3.860 (3)	122
C15—H15A···Cg2^iv	0.96	3.39	3.734 (3)	104
C15—H15B···Cg2^iv	0.96	3.20	3.734 (3)	117

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

Hydrogen-bond geometry (Å, º) top

Cg1and Cg2 are the centroids of the C8–C13 and C1–C5/N1 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2'···O1ⁱ	0.866 (9)	2.076 (11)	2.9107 (18)	161.5 (17)
C7—H7···O1ⁱ	0.9293	2.4820	3.251 (2)	140
C15—H15C···O3ⁱⁱ	0.9599	2.5486	3.469 (4)	161
C4—H4···Cg1ⁱⁱⁱ	0.9300	3.1267	3.821 (2)	133
C13—H13···Cg2ⁱⁱⁱ	0.9300	3.2825	3.860 (3)	122
C15—H15A···Cg2^iv	0.9600	3.3911	3.734 (3)	104
C15—H15B···Cg2^iv	0.9600	3.1984	3.734 (3)	117

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

Acknowledgements

The authors are grateful to the Sophisticated Analytical Instruments Facility, Cochin University of Science and Technology, Kochi-22, India, for the diffraction measurements. RV and RD thank Christ University, Bangalore, India, for financial support.

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