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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 68| Part 2| February 2012| Page o513
doi:10.1107/S1600536812002577

2-(4-Fluoro­phen­yl)-2-oxo­ethyl 2-meth­oxy­benzoate

Arun M. Isloor,a B. Garudachari,a M. N. Satyanarayan,b Thomas Gerber,c Eric Hostenc and Richard Betzc*

aNational Institute of Technology-Karnataka, Department of Chemistry – Organic Electronics Division, Surathkal, Mangalore 575 025, India, bNational Institute of Technology-Karnataka, Department of Physics, Surathkal, Mangalore 575 025, India, and cNelson Mandela Metropolitan University, Summerstrand Campus, Department of Chemistry, University Way, Summerstrand, PO Box 77000, Port Elizabeth 6031, South Africa
*Correspondence e-mail: richard.betz@webmail.co.za

(Received 18 January 2012; accepted 20 January 2012; online 25 January 2012)

In the title compound, C16H13FO4, the aromatic rings enclose an angle of 73.68 (6)°. In the crystal, C—H⋯O and C—H⋯F contacts connect the mol­ecules into a three-dimensional network. The shortest inter­centroid distance between two aromatic π-systems is 3.6679 (7) Å and is apparent between the fluorinated phenyl groups.

Related literature

For general background to photosensitive protective groups and their synthetic potential, see: Sheehan & Umezaw (1973[Sheehan, J. C. & Umezaw, K. (1973). J. Org. Chem. 58, 3771-3773.]); Ruzicka et al. (2002[Ruzicka, R., Zabadal, M. & Klan, P. (2002). Synth. Commun. 32, 2581-2590.]); Litera et al. (2006[Litera, J. K., Loya, A. D. & Klan, P. (2006). J. Org. Chem. 71, 713-723.]); Rather & Reid (1919[Rather, J. B. & Reid, E. (1919). J. Am. Chem. Soc. 41, 75-83.]); Huang et al. (1996[Huang, W., Pian, J., Chen, B., Pei, W. & Ye, X. (1996). Tetrahedron, 52, 10131-10136.]); Gandhi et al. (1995[Gandhi, S. S., Bell, K. L. & Gibson, M. S. (1995). Tetrahedron, 51, 13301-13308.]). For the graph-set analysis of hydrogen bonds, see: Etter et al. (1990[Etter, M. C., MacDonald, J. C. & Bernstein, J. (1990). Acta Cryst. B46, 256-262.]); Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]).

[Scheme 1]

Experimental

Crystal data

  • C16H13FO4

  • Mr = 288.26

  • Monoclinic, P 21 /c

  • a = 7.9370 (3) Å

  • b = 26.4456 (9) Å

  • c = 7.0635 (2) Å

  • β = 113.404 (1)°

  • V = 1360.64 (8) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.11 mm−1

  • T = 200 K

  • 0.43 × 0.32 × 0.27 mm
Data collection

  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2008[Bruker (2008). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.682, Tmax = 0.746

  • 12541 measured reflections

  • 3365 independent reflections

  • 2927 reflections with I > 2σ(I)

  • Rint = 0.027
Refinement

  • R[F2 > 2σ(F2)] = 0.037

  • wR(F2) = 0.098

  • S = 1.04

  • 3365 reflections

  • 191 parameters

  • H-atom parameters constrained

  • Δρmax = 0.27 e Å−3

  • Δρmin = −0.16 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
C16—H16⋯F1i 0.95 2.52 3.4335 (15) 162
C23—H23⋯O1ii 0.95 2.53 3.4004 (15) 152
C25—H25⋯O3iii 0.95 2.34 3.1436 (14) 142
Symmetry codes: (i) -x+1, -y, -z+2; (ii) -x, -y, -z+1; (iii) x, y, z+1.

Data collection: APEX2 (Bruker, 2010[Bruker (2010). APEX2 and SAINT Bruker AXS Inc., Madison, USA.]); cell refinement: SAINT (Bruker, 2010[Bruker (2010). APEX2 and SAINT Bruker AXS Inc., Madison, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]) and Mercury (Macrae et al., 2008[Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.]); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812002577/gk2452sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812002577/gk2452Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812002577/gk2452Isup3.cdx

Supporting information file. DOI: 10.1107/S1600536812002577/gk2452Isup4.cml

checkCIF report


Comment top

Phenacyl benzoates are very useful protecting groups which can easily be cleaved by non-chemical methods. The advantage of photosensitive blocking groups in general is that they can be removed under completely neutral and mild conditions (Sheehan & Umezaw, 1973; Ruzicka et al., 2002; Litera et al., 2006) and therefore used for the identification of organic acids (Rather & Reid, 1919), synthesis of oxazoles, imidazoles (Huang et al., 1996) and benzoxazepine (Gandhi et al., 1995). Keeping this in view, the title compound was synthesized to study its crystal structure.

The title compound is the ester derived of 2-methoxybenzoic acid and 1-(4-fluorophenyl)-2-hydroxyethanone. The least-squares planes defined by the carbon atoms of the two individual aromatic systems intersect at an angle of 73.68 (6)°. The dihedral angle defined by the CO atoms of both carbonyl groups was found at more than 102° (Fig. 1).

In the crystal, C–H···O contacts as well as C–H···F contacts whose range falls invariably by more than 0.1 Å below the sum of van-der-Waals radii of the respective atoms are present. The C–H···O contacts are apparent between both hydrogen atoms in ortho position to the fluorine atom on the phenyl group and have the two different carbonyl groups as acceptors. The C–H···F contact is supported by the hydrogen atom in ortho position to the carboxylic acid group on the second aromatic system. Details about metrical parameters as well as information about the symmetry of these contacts is summarized in Table 1. In terms of graph-set analysis (Etter et al., 1990; Bernstein et al., 1995), the descriptor for the C–H···O contacts is C11(6)R22(18) on the unitary level while the C–H···F contacts require a R22(24) descriptor on the same level. In total, the molecules are connected to a three-dimensional network. The shortest intercentroid distance between two π-systems was measured at 3.6679 (7) Å and is apparent between the fluorinated phenyl groups (Fig. 2).

The packing of the title compound in the crystal structure is shown in Figure 3.

Related literature top

For general background to photosensitive protective groups and their synthetic potential, see: Sheehan & Umezaw (1973); Ruzicka et al. (2002); Litera et al. (2006); Rather & Reid (1919); Huang et al. (1996); Gandhi et al. (1995). For the graph-set analysis of hydrogen bonds, see: Etter et al. (1990); Bernstein et al. (1995).

Experimental top

A mixture of 2-methoxybenzoic acid (1.0 g, 0.0065 mol) potassium carbonate (0.99 g, 0.0072 mol) and 2-bromo-1-(4-fluorophenyl)ethanone (1.41 g, 0.0065 mol) in dimethylformamide (10 ml) was stirred at room temperature for 2 h. On cooling, colorless needle-shaped crystals of 2-(4-fluorophenyl)-2-oxoethyl 2-methoxybenzoate began to separate. These were collected by filtration and recrystallized from ethanol. Yield: 1.62 g, 85.7% (m.p. 359–360 K).

Refinement top

Carbon-bound H atoms were placed in calculated positions (C—H 0.95 Å for aromatic carbon atoms and C—H 0.99 Å for methylene groups) and were included in the refinement in the riding model approximation, with U(H) set to 1.2Ueq(C). The H atoms of the methyl groups were allowed to rotate with a fixed angle around the C—C bond (C—H 0.98 Å) to best fit the experimental electron density (HFIX 137 in the SHELX program suite (Sheldrick, 2008)), with U(H) set to 1.5Ueq(C).

Computing details top

Data collection: APEX2 (Bruker, 2010); cell refinement: SAINT (Bruker, 2010); data reduction: SAINT (Bruker, 2010); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound, with atom labels and anisotropic displacement ellipsoids drawn at the 50% probability level.
[Figure 2] Fig. 2. Intermolecular contacts viewed along [0 0 - 1]. For clarity, only the intermolecular C–H···F contacts are depicted. Symmetry operator: (i) -x + 1, -y, -z + 2.
[Figure 3] Fig. 3. Molecular packing of the title compound viewed along [-1 0 0] (anisotropic displacement ellipsoids drawn at the 50% probability level).
2-(4-Fluorophenyl)-2-oxoethyl 2-methoxybenzoate top
Crystal data top
C16H13FO4F(000) = 600
Mr = 288.26Dx = 1.407 Mg m−3
Monoclinic, P21/cMelting point = 359–360 K
Hall symbol: -P 2ybcMo Kα radiation, λ = 0.71073 Å
a = 7.9370 (3) ÅCell parameters from 8158 reflections
b = 26.4456 (9) Åθ = 2.3–28.3°
c = 7.0635 (2) ŵ = 0.11 mm−1
β = 113.404 (1)°T = 200 K
V = 1360.64 (8) Å3Platelet, colourless
Z = 40.43 × 0.32 × 0.27 mm
Data collection top
Bruker APEXII CCD
diffractometer		3365 independent reflections
Radiation source: fine-focus sealed tube2927 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.027
ϕ and ω scansθmax = 28.3°, θmin = 2.8°
Absorption correction: multi-scan
(SADABS; Bruker, 2008)		h = −10→10
Tmin = 0.682, Tmax = 0.746k = −34→35
12541 measured reflectionsl = −9→9
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.037Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.098H-atom parameters constrained
S = 1.04 w = 1/[σ2(Fo2) + (0.0429P)2 + 0.365P]
where P = (Fo2 + 2Fc2)/3
3365 reflections(Δ/σ)max < 0.001
191 parametersΔρmax = 0.27 e Å−3
0 restraintsΔρmin = −0.16 e Å−3
Crystal data top
C16H13FO4V = 1360.64 (8) Å3
Mr = 288.26Z = 4
Monoclinic, P21/cMo Kα radiation
a = 7.9370 (3) ŵ = 0.11 mm−1
b = 26.4456 (9) ÅT = 200 K
c = 7.0635 (2) Å0.43 × 0.32 × 0.27 mm
β = 113.404 (1)°
Data collection top
Bruker APEXII CCD
diffractometer		3365 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2008)		2927 reflections with I > 2σ(I)
Tmin = 0.682, Tmax = 0.746Rint = 0.027
12541 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0370 restraints
wR(F2) = 0.098H-atom parameters constrained
S = 1.04Δρmax = 0.27 e Å−3
3365 reflectionsΔρmin = −0.16 e Å−3
191 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
F10.06897 (11)−0.10183 (3)1.15257 (13)0.0497 (2)
O10.16097 (12)0.14995 (4)0.54890 (14)0.0429 (2)
O20.44950 (11)0.12318 (3)0.72404 (13)0.0378 (2)
O30.28771 (14)0.03775 (4)0.56649 (13)0.0438 (2)
O40.09706 (11)0.19590 (3)0.19131 (13)0.0399 (2)
C10.31601 (15)0.14617 (4)0.56176 (17)0.0318 (2)
C20.30526 (15)0.04439 (4)0.74269 (16)0.0307 (2)
C30.38626 (16)0.09361 (4)0.85111 (17)0.0344 (2)
H3A0.29190.11270.88030.041*
H3B0.48970.08630.98400.041*
C4−0.0169 (2)0.21960 (6)0.0007 (2)0.0571 (4)
H4A0.02470.2544−0.00120.086*
H4B−0.14450.2198−0.01230.086*
H4C−0.00870.2007−0.11480.086*
C110.39019 (15)0.16557 (4)0.41277 (17)0.0309 (2)
C120.27767 (15)0.19075 (4)0.23052 (18)0.0317 (2)
C130.35424 (18)0.20974 (5)0.0989 (2)0.0402 (3)
H130.27890.2272−0.02300.048*
C140.5388 (2)0.20346 (5)0.1442 (2)0.0473 (3)
H140.58950.21700.05370.057*
C150.65086 (18)0.17783 (5)0.3194 (2)0.0466 (3)
H150.77730.17310.34840.056*
C160.57610 (17)0.15923 (5)0.4521 (2)0.0391 (3)
H160.65300.14170.57290.047*
C210.24735 (14)0.00579 (4)0.85746 (16)0.0282 (2)
C220.15576 (15)−0.03738 (4)0.75205 (17)0.0325 (2)
H220.1341−0.04150.61060.039*
C230.09629 (15)−0.07416 (4)0.85026 (18)0.0354 (2)
H230.0339−0.10350.77890.043*
C240.13080 (15)−0.06672 (4)1.05523 (18)0.0345 (2)
C250.22246 (16)−0.02547 (5)1.16654 (17)0.0348 (2)
H250.2459−0.02221.30880.042*
C260.27973 (15)0.01127 (4)1.06578 (16)0.0313 (2)
H260.34160.04051.13890.038*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
F10.0500 (5)0.0474 (4)0.0545 (5)−0.0017 (3)0.0238 (4)0.0127 (3)
O10.0357 (5)0.0503 (5)0.0443 (5)0.0094 (4)0.0176 (4)0.0130 (4)
O20.0321 (4)0.0377 (4)0.0370 (4)−0.0012 (3)0.0067 (3)0.0070 (3)
O30.0579 (6)0.0429 (5)0.0307 (4)−0.0036 (4)0.0179 (4)−0.0037 (3)
O40.0325 (4)0.0410 (5)0.0434 (5)0.0045 (3)0.0123 (4)0.0132 (4)
C10.0322 (5)0.0260 (5)0.0333 (5)0.0010 (4)0.0090 (4)−0.0001 (4)
C20.0283 (5)0.0318 (5)0.0276 (5)0.0049 (4)0.0065 (4)0.0002 (4)
C30.0365 (6)0.0319 (5)0.0294 (5)−0.0006 (4)0.0074 (4)0.0018 (4)
C40.0409 (7)0.0620 (9)0.0594 (8)0.0071 (6)0.0105 (6)0.0307 (7)
C110.0312 (5)0.0239 (5)0.0368 (5)−0.0018 (4)0.0125 (4)−0.0028 (4)
C120.0338 (5)0.0227 (5)0.0383 (6)−0.0021 (4)0.0140 (4)−0.0021 (4)
C130.0480 (7)0.0314 (6)0.0443 (6)−0.0039 (5)0.0216 (5)0.0018 (5)
C140.0528 (8)0.0405 (7)0.0609 (8)−0.0084 (6)0.0355 (7)−0.0028 (6)
C150.0366 (6)0.0422 (7)0.0670 (9)−0.0050 (5)0.0270 (6)−0.0084 (6)
C160.0329 (6)0.0336 (6)0.0484 (7)0.0003 (4)0.0134 (5)−0.0029 (5)
C210.0251 (5)0.0292 (5)0.0271 (5)0.0044 (4)0.0070 (4)−0.0017 (4)
C220.0306 (5)0.0348 (5)0.0281 (5)0.0018 (4)0.0074 (4)−0.0046 (4)
C230.0302 (5)0.0323 (5)0.0389 (6)0.0000 (4)0.0085 (4)−0.0040 (4)
C240.0293 (5)0.0339 (6)0.0399 (6)0.0056 (4)0.0134 (4)0.0073 (4)
C250.0353 (6)0.0403 (6)0.0281 (5)0.0069 (5)0.0118 (4)0.0004 (4)
C260.0306 (5)0.0310 (5)0.0286 (5)0.0035 (4)0.0079 (4)−0.0045 (4)
Geometric parameters (Å, º) top
F1—C241.3577 (13)C13—C141.3799 (19)
O1—C11.2015 (14)C13—H130.9500
O2—C11.3571 (13)C14—C151.381 (2)
O2—C31.4236 (14)C14—H140.9500
O3—C21.2090 (14)C15—C161.3834 (19)
O4—C121.3545 (14)C15—H150.9500
O4—C41.4339 (15)C16—H160.9500
C1—C111.4865 (16)C21—C261.3971 (14)
C2—C211.4853 (15)C21—C221.3988 (15)
C2—C31.5177 (15)C22—C231.3820 (17)
C3—H3A0.9900C22—H220.9500
C3—H3B0.9900C23—C241.3765 (17)
C4—H4A0.9800C23—H230.9500
C4—H4B0.9800C24—C251.3722 (17)
C4—H4C0.9800C25—C261.3835 (17)
C11—C161.3990 (16)C25—H250.9500
C11—C121.4089 (15)C26—H260.9500
C12—C131.3906 (16)
C1—O2—C3115.22 (9)C12—C13—H13119.8
C12—O4—C4117.22 (10)C13—C14—C15120.87 (12)
O1—C1—O2122.26 (11)C13—C14—H14119.6
O1—C1—C11126.84 (10)C15—C14—H14119.6
O2—C1—C11110.90 (9)C14—C15—C16119.00 (12)
O3—C2—C21121.88 (10)C14—C15—H15120.5
O3—C2—C3119.77 (10)C16—C15—H15120.5
C21—C2—C3118.35 (9)C15—C16—C11121.69 (12)
O2—C3—C2109.74 (9)C15—C16—H16119.2
O2—C3—H3A109.7C11—C16—H16119.2
C2—C3—H3A109.7C26—C21—C22118.98 (10)
O2—C3—H3B109.7C26—C21—C2122.43 (10)
C2—C3—H3B109.7C22—C21—C2118.59 (9)
H3A—C3—H3B108.2C23—C22—C21121.07 (10)
O4—C4—H4A109.5C23—C22—H22119.5
O4—C4—H4B109.5C21—C22—H22119.5
H4A—C4—H4B109.5C24—C23—C22117.55 (11)
O4—C4—H4C109.5C24—C23—H23121.2
H4A—C4—H4C109.5C22—C23—H23121.2
H4B—C4—H4C109.5F1—C24—C25118.00 (11)
C16—C11—C12118.28 (11)F1—C24—C23118.29 (11)
C16—C11—C1120.09 (10)C25—C24—C23123.70 (11)
C12—C11—C1121.63 (10)C24—C25—C26118.12 (10)
O4—C12—C13122.34 (11)C24—C25—H25120.9
O4—C12—C11118.01 (10)C26—C25—H25120.9
C13—C12—C11119.65 (11)C25—C26—C21120.56 (10)
C14—C13—C12120.49 (12)C25—C26—H26119.7
C14—C13—H13119.8C21—C26—H26119.7
C3—O2—C1—O114.38 (15)C13—C14—C15—C16−1.2 (2)
C3—O2—C1—C11−166.53 (9)C14—C15—C16—C110.23 (19)
C1—O2—C3—C275.18 (12)C12—C11—C16—C151.31 (17)
O3—C2—C3—O2−6.54 (15)C1—C11—C16—C15−178.44 (11)
C21—C2—C3—O2174.23 (9)O3—C2—C21—C26174.92 (11)
O1—C1—C11—C16178.44 (11)C3—C2—C21—C26−5.87 (15)
O2—C1—C11—C16−0.61 (14)O3—C2—C21—C22−5.59 (16)
O1—C1—C11—C12−1.31 (18)C3—C2—C21—C22173.62 (10)
O2—C1—C11—C12179.65 (9)C26—C21—C22—C230.49 (16)
C4—O4—C12—C133.34 (17)C2—C21—C22—C23−179.02 (10)
C4—O4—C12—C11−177.26 (11)C21—C22—C23—C24−0.10 (16)
C16—C11—C12—O4178.72 (10)C22—C23—C24—F1178.27 (10)
C1—C11—C12—O4−1.53 (15)C22—C23—C24—C25−0.94 (17)
C16—C11—C12—C13−1.87 (16)F1—C24—C25—C26−177.68 (10)
C1—C11—C12—C13177.88 (10)C23—C24—C25—C261.53 (17)
O4—C12—C13—C14−179.70 (11)C24—C25—C26—C21−1.08 (16)
C11—C12—C13—C140.91 (17)C22—C21—C26—C250.12 (16)
C12—C13—C14—C150.7 (2)C2—C21—C26—C25179.61 (10)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C16—H16···F1i0.952.523.4335 (15)162
C23—H23···O1ii0.952.533.4004 (15)152
C25—H25···O3iii0.952.343.1436 (14)142
Symmetry codes: (i) −x+1, −y, −z+2; (ii) −x, −y, −z+1; (iii) x, y, z+1.

Experimental details

Crystal data
Chemical formulaC16H13FO4
Mr288.26
Crystal system, space groupMonoclinic, P21/c
Temperature (K)200
a, b, c (Å)7.9370 (3), 26.4456 (9), 7.0635 (2)
β (°) 113.404 (1)
V (Å3)1360.64 (8)
Z4
Radiation typeMo Kα
µ (mm−1)0.11
Crystal size (mm)0.43 × 0.32 × 0.27
Data collection
DiffractometerBruker APEXII CCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2008)
Tmin, Tmax0.682, 0.746
No. of measured, independent and
observed [I > 2σ(I)] reflections		12541, 3365, 2927
Rint0.027
(sin θ/λ)max (Å−1)0.667
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.037, 0.098, 1.04
No. of reflections3365
No. of parameters191
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å−3)0.27, −0.16

Computer programs: APEX2 (Bruker, 2010), SAINT (Bruker, 2010), SHELXS97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and Mercury (Macrae et al., 2008), SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C16—H16···F1i0.952.523.4335 (15)162
C23—H23···O1ii0.952.533.4004 (15)152
C25—H25···O3iii0.952.343.1436 (14)142
Symmetry codes: (i) −x+1, −y, −z+2; (ii) −x, −y, −z+1; (iii) x, y, z+1.
 

Acknowledgements

AMI is thankful to the Department of Atomic Energy, Board for Research in Nuclear Sciences, Government of India, for the Young Scientist award. SMN thanks the Department of Information Technology, New Delhi, India, for financial support.

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ISSN: 2056-9890
Volume 68| Part 2| February 2012| Page o513
doi:10.1107/S1600536812002577
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