2-(2,4-Dichloro­phen­yl)-2-oxoethyl 4-meth­oxy­benzoate

Fun, H.-K.; Chia, T.S.; Shenvi, S.; Isloor, A.M.; Garudachari, B.

doi:10.1107/S1600536811048720

organic compounds

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ISSN: 2056-9890

Volume 67| Part 12| December 2011| Page o3379

https://doi.org/10.1107/S1600536811048720

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2-(2,4-Dichlorophenyl)-2-oxoethyl 4-methoxybenzoate

Hoong-Kun Fun,^a ^*‡ Tze Shyang Chia,^a Seema Shenvi,^b Arun M. Isloor ^b and B. Garudachari ^b

^aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and ^bMedicinal Chemstry Division, Department of Chemistry, National Institute of Technology-Karnataka, Surathkal, Mangalore 575 025, India
^*Correspondence e-mail: hkfun@usm.my

(Received 15 November 2011; accepted 16 November 2011; online 19 November 2011)

In the title compound, C₁₆H₁₂Cl₂O₄, the dihedral angle between the benzene rings is 70.11 (6)°. In the crystal, molecules are linked by C—H⋯O hydrogen bonds into a three-dimensional network. A C—H⋯π interaction is also observed.

Related literature

For related structures and background to phenacyl benzoates, see: Fun et al. (2011a ,b ). For reference bond lengths, see: Allen et al. (1987 ). For stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ).

Experimental

Crystal data

C₁₆H₁₂Cl₂O₄
M_r = 339.16
Monoclinic, P 2₁ /c
a = 9.0508 (1) Å
b = 7.0846 (1) Å
c = 23.3337 (3) Å
β = 102.509 (1)°
V = 1460.67 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.46 mm⁻¹
T = 100 K
0.36 × 0.30 × 0.13 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.852, T_max = 0.942
24788 measured reflections
6502 independent reflections
5027 reflections with I > 2σ(I)
R_int = 0.037

Refinement

R[F² > 2σ(F²)] = 0.039
wR(F²) = 0.097
S = 1.02
6502 reflections
200 parameters
H-atom parameters constrained
Δρ_max = 0.52 e Å⁻³
Δρ_min = −0.34 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C1–C6 benzene ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2A⋯O4ⁱ	0.95	2.54	3.4809 (13)	173
C5—H5A⋯O2ⁱⁱ	0.95	2.35	3.2745 (15)	164
C8—H8B⋯O3ⁱⁱⁱ	0.99	2.50	3.4124 (17)	153
C16—H16C⋯Cg1^iv	0.98	2.84	3.5655 (15)	132
Symmetry codes: (i) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (ii) -x+2, -y+1, -z+2; (iii) -x+1, -y+1, -z+2; (iv) -x+2, -y, -z+2.

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT; 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: https://doi.org/10.1107/S1600536811048720/hb6515sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536811048720/hb6515Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536811048720/hb6515Isup3.cml

checkCIF report

Comment top

As part of our ongoing studies of phenacyl benzoates (Fun et al., 2011a,b), we hereby report the crystal structure of the title compound, (I).

The molecular structure of the title compound is shown in Fig. 1. The C1–C6 benzene ring [maximum deviation of 0.008 (1) Å at atom C4] and C10–C15 benzene ring [maximum deviation of 0.005 (1) Å at atoms C12 and C15] make a dihedral angle of 70.11 (6)° with each other. Bond lengths (Allen et al., 1987) and angles are within normal ranges and are comparable to related structures (Fun et al., 2011a,b).

In the crystal structure (Fig. 2), the molecules are interconnected by C2—H2A···O4, C5—H5A···O2 and C8—H8B···O3 hydrogen bonds (Table 1) forming a three-dimensional network. The crystal structure is further stabilized by C—H···π interactions, involving the centroids of C1–C6 benzene rings.

Related literature top

For related structures and background to phenacyl benzoates, see: Fun et al. (2011a,b). For reference bond lengths, see: Allen et al. (1987). For stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986).

Experimental top

The mixture of 4-methoxybenzoic acid (340.4 mg, 0.0022 mol), potassium carbonate (340.3 mg, 0.0025 mol) and 2-chloro-1-(2,4-dichlorophenyl) ethanone (500 mg, 0.0022 mol) in DMF (10 ml) was stirred at room temperature for 2 h. On cooling, colorless needle-shaped crystals of 2-(2,4-dichlorophenyl)-2-oxoethyl 4-methoxybenzoate begins to separate out. It was collected by filtration and then recrystallized from ethanol to yield colourless plates of (I). Yield: 691.6 mg, 92.7%, M.p.: 385–386 K.

Structure description top

As part of our ongoing studies of phenacyl benzoates (Fun et al., 2011a,b), we hereby report the crystal structure of the title compound, (I).

For related structures and background to phenacyl benzoates, see: Fun et al. (2011a,b). For reference bond lengths, see: Allen et al. (1987). For stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986).

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); 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 with 50% probability displacement ellipsoids.
	Fig. 2. The crystal packing of the title compound. The dashed lines represent the hydrogen bonds.

2-(2,4-Dichlorophenyl)-2-oxoethyl 4-methoxybenzoate top

Crystal data top

C₁₆H₁₂Cl₂O₄	F(000) = 696
M_r = 339.16	D_x = 1.542 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 6774 reflections
a = 9.0508 (1) Å	θ = 2.3–35.0°
b = 7.0846 (1) Å	µ = 0.46 mm⁻¹
c = 23.3337 (3) Å	T = 100 K
β = 102.509 (1)°	Plate, colourless
V = 1460.67 (3) Å³	0.36 × 0.30 × 0.13 mm
Z = 4

Data collection top

Bruker SMART APEXII CCD diffractometer	6502 independent reflections
Radiation source: fine-focus sealed tube	5027 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.037
φ and ω scans	θ_max = 35.2°, θ_min = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −14→12
T_min = 0.852, T_max = 0.942	k = −11→10
24788 measured reflections	l = −36→37

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) = 0.097	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.040P)² + 0.5816P] where P = (F_o² + 2F_c²)/3
6502 reflections	(Δ/σ)_max = 0.004
200 parameters	Δρ_max = 0.52 e Å⁻³
0 restraints	Δρ_min = −0.34 e Å⁻³

Crystal data top

C₁₆H₁₂Cl₂O₄	V = 1460.67 (3) Å³
M_r = 339.16	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 9.0508 (1) Å	µ = 0.46 mm⁻¹
b = 7.0846 (1) Å	T = 100 K
c = 23.3337 (3) Å	0.36 × 0.30 × 0.13 mm
β = 102.509 (1)°

Data collection top

Bruker SMART APEXII CCD diffractometer	6502 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	5027 reflections with I > 2σ(I)
T_min = 0.852, T_max = 0.942	R_int = 0.037
24788 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.039	0 restraints
wR(F²) = 0.097	H-atom parameters constrained
S = 1.02	Δρ_max = 0.52 e Å⁻³
6502 reflections	Δρ_min = −0.34 e Å⁻³
200 parameters

Special details top

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

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	0.66881 (3)	0.47740 (4)	1.178052 (11)	0.01926 (7)
Cl2	0.97532 (4)	1.12299 (5)	1.190485 (14)	0.02429 (7)
O1	0.65268 (10)	0.12541 (13)	1.01931 (3)	0.01802 (16)
O2	0.89431 (11)	0.33741 (15)	1.03290 (4)	0.0262 (2)
O3	0.56227 (12)	0.33618 (14)	0.94784 (4)	0.0265 (2)
O4	0.67141 (9)	−0.37683 (13)	0.79718 (3)	0.01786 (16)
C1	0.78521 (12)	0.62113 (17)	1.14699 (5)	0.01504 (19)
C2	0.82728 (12)	0.79099 (17)	1.17576 (5)	0.01596 (19)
H2A	0.7914	0.8237	1.2098	0.019*
C3	0.92243 (12)	0.91200 (17)	1.15397 (5)	0.0168 (2)
C4	0.97624 (13)	0.86750 (18)	1.10412 (5)	0.0186 (2)
H4A	1.0399	0.9525	1.0892	0.022*
C5	0.93461 (12)	0.69604 (18)	1.07679 (5)	0.0166 (2)
H5A	0.9726	0.6634	1.0432	0.020*
C6	0.83829 (12)	0.56876 (17)	1.09690 (4)	0.01481 (19)
C7	0.80621 (12)	0.38880 (18)	1.06248 (5)	0.0167 (2)
C8	0.66353 (13)	0.27437 (18)	1.06150 (5)	0.0177 (2)
H8A	0.6667	0.2205	1.1009	0.021*
H8B	0.5736	0.3572	1.0511	0.021*
C9	0.60826 (13)	0.17893 (18)	0.96250 (5)	0.0173 (2)
C10	0.62482 (12)	0.02595 (17)	0.92132 (4)	0.01478 (18)
C11	0.56119 (12)	0.05046 (17)	0.86144 (5)	0.01633 (19)
H11A	0.5058	0.1620	0.8484	0.020*
C12	0.57849 (12)	−0.08669 (18)	0.82128 (5)	0.0163 (2)
H12A	0.5342	−0.0699	0.7808	0.020*
C13	0.66111 (12)	−0.24992 (17)	0.84031 (5)	0.01497 (19)
C14	0.72520 (13)	−0.27659 (18)	0.89986 (5)	0.0168 (2)
H14A	0.7814	−0.3876	0.9129	0.020*
C15	0.70546 (13)	−0.13853 (17)	0.93974 (5)	0.0166 (2)
H15A	0.7477	−0.1566	0.9803	0.020*
C16	0.75581 (14)	−0.54602 (19)	0.81472 (5)	0.0216 (2)
H16A	0.7483	−0.6293	0.7807	0.032*
H16B	0.7147	−0.6104	0.8450	0.032*
H16C	0.8622	−0.5140	0.8305	0.032*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.02234 (12)	0.01956 (14)	0.01897 (11)	−0.00520 (10)	0.01125 (9)	−0.00190 (10)
Cl2	0.02641 (14)	0.01913 (15)	0.02799 (14)	−0.00677 (11)	0.00735 (11)	−0.00626 (11)
O1	0.0223 (4)	0.0167 (4)	0.0153 (3)	−0.0022 (3)	0.0047 (3)	−0.0019 (3)
O2	0.0247 (4)	0.0287 (5)	0.0300 (4)	−0.0050 (4)	0.0162 (4)	−0.0101 (4)
O3	0.0382 (5)	0.0181 (5)	0.0227 (4)	0.0068 (4)	0.0051 (4)	−0.0010 (3)
O4	0.0203 (4)	0.0166 (4)	0.0168 (3)	0.0010 (3)	0.0041 (3)	−0.0025 (3)
C1	0.0136 (4)	0.0171 (5)	0.0151 (4)	−0.0018 (4)	0.0047 (3)	0.0008 (4)
C2	0.0160 (4)	0.0166 (5)	0.0154 (4)	−0.0001 (4)	0.0036 (3)	−0.0011 (4)
C3	0.0161 (4)	0.0151 (5)	0.0186 (4)	−0.0009 (4)	0.0026 (3)	−0.0003 (4)
C4	0.0182 (5)	0.0189 (6)	0.0194 (5)	−0.0026 (4)	0.0061 (4)	0.0017 (4)
C5	0.0156 (4)	0.0195 (6)	0.0157 (4)	−0.0005 (4)	0.0056 (3)	0.0011 (4)
C6	0.0138 (4)	0.0170 (5)	0.0139 (4)	−0.0008 (4)	0.0035 (3)	−0.0004 (4)
C7	0.0166 (4)	0.0190 (6)	0.0152 (4)	−0.0012 (4)	0.0051 (3)	−0.0008 (4)
C8	0.0196 (5)	0.0177 (6)	0.0170 (4)	−0.0037 (4)	0.0069 (4)	−0.0040 (4)
C9	0.0174 (5)	0.0179 (5)	0.0168 (4)	−0.0015 (4)	0.0044 (4)	−0.0012 (4)
C10	0.0152 (4)	0.0143 (5)	0.0151 (4)	−0.0022 (4)	0.0039 (3)	−0.0001 (4)
C11	0.0165 (4)	0.0161 (5)	0.0165 (4)	0.0008 (4)	0.0037 (3)	0.0018 (4)
C12	0.0163 (4)	0.0186 (6)	0.0139 (4)	0.0002 (4)	0.0028 (3)	0.0015 (4)
C13	0.0140 (4)	0.0158 (5)	0.0156 (4)	−0.0024 (4)	0.0041 (3)	−0.0001 (4)
C14	0.0181 (5)	0.0154 (5)	0.0164 (4)	0.0002 (4)	0.0027 (3)	0.0007 (4)
C15	0.0179 (5)	0.0174 (5)	0.0139 (4)	−0.0006 (4)	0.0021 (3)	0.0007 (4)
C16	0.0243 (5)	0.0167 (6)	0.0242 (5)	0.0015 (4)	0.0061 (4)	−0.0013 (4)

Geometric parameters (Å, º) top

Cl1—C1	1.7329 (11)	C7—C8	1.5207 (16)
Cl2—C3	1.7357 (13)	C8—H8A	0.9900
O1—C9	1.3535 (14)	C8—H8B	0.9900
O1—C8	1.4320 (14)	C9—C10	1.4774 (16)
O2—C7	1.2178 (13)	C10—C15	1.3927 (16)
O3—C9	1.2123 (15)	C10—C11	1.4019 (15)
O4—C13	1.3677 (14)	C11—C12	1.3821 (16)
O4—C16	1.4326 (16)	C11—H11A	0.9500
C1—C2	1.3904 (16)	C12—C13	1.3963 (17)
C1—C6	1.4063 (14)	C12—H12A	0.9500
C2—C3	1.3874 (16)	C13—C14	1.3980 (15)
C2—H2A	0.9500	C14—C15	1.3878 (16)
C3—C4	1.3912 (16)	C14—H14A	0.9500
C4—C5	1.3857 (17)	C15—H15A	0.9500
C4—H4A	0.9500	C16—H16A	0.9800
C5—C6	1.4037 (16)	C16—H16B	0.9800
C5—H5A	0.9500	C16—H16C	0.9800
C6—C7	1.5013 (17)

C9—O1—C8	115.37 (10)	H8A—C8—H8B	108.2
C13—O4—C16	117.18 (9)	O3—C9—O1	123.00 (11)
C2—C1—C6	121.51 (10)	O3—C9—C10	124.59 (10)
C2—C1—Cl1	115.74 (8)	O1—C9—C10	112.40 (10)
C6—C1—Cl1	122.73 (9)	C15—C10—C11	119.07 (10)
C3—C2—C1	118.99 (10)	C15—C10—C9	122.23 (10)
C3—C2—H2A	120.5	C11—C10—C9	118.67 (10)
C1—C2—H2A	120.5	C12—C11—C10	120.42 (11)
C2—C3—C4	121.60 (11)	C12—C11—H11A	119.8
C2—C3—Cl2	118.64 (9)	C10—C11—H11A	119.8
C4—C3—Cl2	119.76 (9)	C11—C12—C13	119.88 (10)
C5—C4—C3	118.29 (11)	C11—C12—H12A	120.1
C5—C4—H4A	120.9	C13—C12—H12A	120.1
C3—C4—H4A	120.9	O4—C13—C12	115.32 (9)
C4—C5—C6	122.41 (10)	O4—C13—C14	124.26 (11)
C4—C5—H5A	118.8	C12—C13—C14	120.42 (10)
C6—C5—H5A	118.8	C15—C14—C13	119.03 (11)
C5—C6—C1	117.19 (11)	C15—C14—H14A	120.5
C5—C6—C7	115.39 (9)	C13—C14—H14A	120.5
C1—C6—C7	127.40 (10)	C14—C15—C10	121.18 (10)
O2—C7—C6	118.85 (10)	C14—C15—H15A	119.4
O2—C7—C8	119.36 (11)	C10—C15—H15A	119.4
C6—C7—C8	121.73 (9)	O4—C16—H16A	109.5
O1—C8—C7	109.56 (9)	O4—C16—H16B	109.5
O1—C8—H8A	109.8	H16A—C16—H16B	109.5
C7—C8—H8A	109.8	O4—C16—H16C	109.5
O1—C8—H8B	109.8	H16A—C16—H16C	109.5
C7—C8—H8B	109.8	H16B—C16—H16C	109.5

C6—C1—C2—C3	0.75 (17)	C6—C7—C8—O1	172.24 (10)
Cl1—C1—C2—C3	178.95 (9)	C8—O1—C9—O3	−8.97 (16)
C1—C2—C3—C4	0.12 (17)	C8—O1—C9—C10	170.10 (9)
C1—C2—C3—Cl2	−179.57 (9)	O3—C9—C10—C15	166.89 (12)
C2—C3—C4—C5	−1.14 (17)	O1—C9—C10—C15	−12.17 (15)
Cl2—C3—C4—C5	178.55 (9)	O3—C9—C10—C11	−10.99 (17)
C3—C4—C5—C6	1.34 (17)	O1—C9—C10—C11	169.95 (10)
C4—C5—C6—C1	−0.51 (17)	C15—C10—C11—C12	−0.08 (16)
C4—C5—C6—C7	−179.40 (11)	C9—C10—C11—C12	177.86 (10)
C2—C1—C6—C5	−0.56 (16)	C10—C11—C12—C13	−0.65 (17)
Cl1—C1—C6—C5	−178.63 (8)	C16—O4—C13—C12	179.72 (10)
C2—C1—C6—C7	178.18 (11)	C16—O4—C13—C14	−1.06 (16)
Cl1—C1—C6—C7	0.11 (17)	C11—C12—C13—O4	179.94 (10)
C5—C6—C7—O2	21.81 (16)	C11—C12—C13—C14	0.69 (17)
C1—C6—C7—O2	−156.95 (12)	O4—C13—C14—C15	−179.17 (10)
C5—C6—C7—C8	−155.42 (11)	C12—C13—C14—C15	0.00 (16)
C1—C6—C7—C8	25.83 (17)	C13—C14—C15—C10	−0.75 (17)
C9—O1—C8—C7	−75.93 (12)	C11—C10—C15—C14	0.79 (17)
O2—C7—C8—O1	−4.98 (16)	C9—C10—C15—C14	−177.08 (11)

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C1–C6 benzene ring.

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2A···O4ⁱ	0.95	2.54	3.4809 (13)	173
C5—H5A···O2ⁱⁱ	0.95	2.35	3.2745 (15)	164
C8—H8B···O3ⁱⁱⁱ	0.99	2.50	3.4124 (17)	153
C16—H16C···Cg1^iv	0.98	2.84	3.5655 (15)	132

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

Experimental details

Crystal data
Chemical formula	C₁₆H₁₂Cl₂O₄
M_r	339.16
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	9.0508 (1), 7.0846 (1), 23.3337 (3)
β (°)	102.509 (1)
V (Å³)	1460.67 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.46
Crystal size (mm)	0.36 × 0.30 × 0.13

Data collection
Diffractometer	Bruker SMART APEXII CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.852, 0.942
No. of measured, independent and observed [I > 2σ(I)] reflections	24788, 6502, 5027
R_int	0.037
(sin θ/λ)_max (Å⁻¹)	0.810

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.039, 0.097, 1.02
No. of reflections	6502
No. of parameters	200
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.52, −0.34

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C1–C6 benzene ring.

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2A···O4ⁱ	0.95	2.54	3.4809 (13)	173
C5—H5A···O2ⁱⁱ	0.95	2.35	3.2745 (15)	164
C8—H8B···O3ⁱⁱⁱ	0.99	2.50	3.4124 (17)	153
C16—H16C···Cg1^iv	0.98	2.84	3.5655 (15)	132

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

Footnotes

‡Thomson Reuters ResearcherID: A-3561-2009.

Acknowledgements

HKF and TSC thank Universiti Sains Malaysia (USM) for the Research University Grant (1001/PFIZIK/811160). TSC thanks the Malaysian Government and USM for the award of the post of Research Officer under the Research University Grant (1001/PSKBP/8630013). AMI thanks the Department of Atomic Energy, Board for Research in Nuclear Sciences, Government of India, for the Young Scientist award.

References

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