4-Bromo-N-phenyl­benzamide

Fun, H.-K.; Chantrapromma, S.; Sripet, W.; Ruanwas, P.; Boonnak, N.

doi:10.1107/S1600536812013487

organic compounds

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ISSN: 2056-9890

Volume 68| Part 4| April 2012| Pages o1269-o1270

doi:10.1107/S1600536812013487

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4-Bromo-N-phenylbenzamide

Hoong-Kun Fun,^a ^*‡ Suchada Chantrapromma,^b § Weerawat Sripet,^b Pumsak Ruanwas ^b and Nawong Boonnak ^b

^aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and ^bCrystal Materials Research Unit, Department of Chemistry, Faculty of Science, Prince of Songkla University, Hat-Yai, Songkhla 90112, Thailand
^*Correspondence e-mail: hkfun@usm.my

(Received 20 March 2012; accepted 28 March 2012; online 31 March 2012)

The molecule of the title benzamide derivative, C₁₃H₁₀BrNO, is twisted with the dihedral angle between the phenyl and 4-bromophenyl rings being 58.63 (9)°. The central N—C=O plane makes dihedral angles of 30.2 (2) and 29.2 (2)° with the phenyl and 4-bromophenyl rings, respectively. In the crystal, molecules are linked by N—H⋯O hydrogen bonds into chains along [100]. C—H⋯π contacts combine with the N—H⋯O hydrogen bonds, to form a three-dimensional network.

Related literature

For bond-length data, see: Allen et al. (1987 ). For related structures, see: Johnston & Taylor (2011 ); Li & Cui (2011 ); Saeed et al. (2008 ); Sripet et al. (2012 ). For background to and applications of benzamide derivatives, see: Boonleang & Tanthana (2010 ); Brown et al. (1991 ); Hu et al. (2008 ); Mobinikhaledi et al. (2006 ); Olsson et al. (2002 ); World Health Organization (2003 ); Xu et al. (2009 ). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ).

Experimental

Crystal data

C₁₃H₁₀BrNO
M_r = 276.12
Triclinic, $[P \overline 1]$
a = 5.3552 (2) Å
b = 7.6334 (2) Å
c = 13.9956 (5) Å
α = 105.757 (3)°
β = 100.585 (3)°
γ = 90.086 (2)°
V = 540.45 (3) Å³
Z = 2
Mo Kα radiation
μ = 3.78 mm⁻¹
T = 100 K
0.29 × 0.09 × 0.07 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.406, T_max = 0.791
11303 measured reflections
3844 independent reflections
3193 reflections with I > 2σ(I)
R_int = 0.032

Refinement

R[F² > 2σ(F²)] = 0.032
wR(F²) = 0.076
S = 1.08
3844 reflections
149 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.66 e Å⁻³
Δρ_min = −0.68 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C1–C6 and C8–C13 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N1⋯O1ⁱ	0.84 (3)	2.37 (3)	3.150 (2)	156 (2)
C2—H2A⋯Cg2ⁱⁱ	0.95	2.77	3.4855 (19)	132
C5—H5A⋯Cg2ⁱⁱⁱ	0.95	2.70	3.4258 (19)	134
C10—H10A⋯Cg1^iv	0.95	2.90	3.5444 (19)	126
C13—H13A⋯Cg1^v	0.95	2.84	3.4950 (19)	127
Symmetry codes: (i) x-1, y, z; (ii) -x+2, -y, -z; (iii) -x+1, -y+1, -z; (iv) -x+1, -y, -z; (v) -x+2, -y+1, -z.

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); 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: 10.1107/S1600536812013487/sj5220sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812013487/sj5220Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812013487/sj5220Isup3.cml

checkCIF report

Comment top

Benzamides are recognised as one of the bioactive skeletons, and some benzamide derivatives exhibit various potent pharmaceutical activities (Brown et al., 1991; Hu et al., 2008). They have been developed as anti-tumor (Olsson et al., 2002), antibacterial (Mobinikhaledi et al., 2006) and anti-Alzheimer's agents (Xu et al., 2009). Cisapride (CIS) is an effective benzamide derived drug which can act as a gastrointestinal prokinetic agent. It also has restricted usage for the treatment of gastroesophageal reflux disease in some countries (World Health Organization, 2003) due to its cardiac side effects. The formulation of a more stable CIS oral suspension was studied (Boonleang & Tanthana, 2010). We have synthesized several N-phenylbenzamide derivatives in order to evaluate their antibacterial and anti-Alzheimer's activities, and the structure of the title benzamide derivative (I) is reported here.

The molecule of the title benzamide derivative (Fig. 1), C₁₃H₁₀BrNO, is twisted with the dihedral angle between the phenyl and 4-bromophenyl rings being 58.63 (9)°. The central N-C=O plane is twisted with respect to the two neighbouring ring planes forming dihedral angles of 30.2 (2) and 29.2 (2) ° with the phenyl and 4-bromophenyl rings respectively, and with torsion angles C2–C1–C7–O1 = -28.1 (3)° and C7–N1–C8–C13 = -30.2 (3)°. Bond distances are within normal ranges (Allen et al., 1987) and are comparable to those found in related structures (Johnston & Taylor, 2011; Li & Cui, 2011; Saeed et al., 2008; Sripet et al., 2012).

In the crystal packing (Fig. 2), the molecules are linked by N—H···O hydrogen bonds (Table 1) into chains along the [100] direction. C—H···π contacts involving H atoms from both the phenyl and 4-bromophenyl rings combine with the N—H···O hydrogen bonds to form a 3-dimensional network (Table 1).

Related literature top

For bond-length data, see: Allen et al. (1987). For related structures, see: Johnston & Taylor (2011); Li & Cui (2011); Saeed et al. (2008); Sripet et al. (2012). For background to and applications of benzamide derivatives, see: Boonleang & Tanthana (2010); Brown et al. (1991); Hu et al. (2008); Mobinikhaledi et al. (2006); Olsson et al. (2002); World Health Organization (2003); Xu et al. (2009). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986).

Experimental top

To the solution of 4-bromobenzoyl chloride (0.20 g, 0.91 mmol) in acetone (10 ml), aniline (0.12 ml, 1.37 mmol) was added and refluxed for 6 h. After the reaction was completed, a gray solid mass formed which was filtered and washed with distilled water. Colorless needle-shaped single crystals of the title compound suitable for X-ray structure determination were recrystallized from acetone/CH₃OH (1:1 v/v) by slow evaporation of the solvent at room temperature over a week, Mp. 474-475 K.

Structure description top

For bond-length data, see: Allen et al. (1987). For related structures, see: Johnston & Taylor (2011); Li & Cui (2011); Saeed et al. (2008); Sripet et al. (2012). For background to and applications of benzamide derivatives, see: Boonleang & Tanthana (2010); Brown et al. (1991); Hu et al. (2008); Mobinikhaledi et al. (2006); Olsson et al. (2002); World Health Organization (2003); Xu et al. (2009). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986).

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 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 50% probability displacement ellipsoids and the atom-numbering scheme.
	Fig. 2. The crystal packing of the title compound viewed along the b axis, showing the molecular chains along the [100] direction. N—H···O hydrogen bonds were drawn as dashed lines.

4-Bromo-N-phenylbenzamide top

Crystal data top

C₁₃H₁₀BrNO	Z = 2
M_r = 276.12	F(000) = 276
Triclinic, P1	D_x = 1.697 Mg m⁻³
Hall symbol: -P 1	Melting point = 474–475 K
a = 5.3552 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 7.6334 (2) Å	Cell parameters from 3844 reflections
c = 13.9956 (5) Å	θ = 2.8–32.5°
α = 105.757 (3)°	µ = 3.78 mm⁻¹
β = 100.585 (3)°	T = 100 K
γ = 90.086 (2)°	Needle, colorless
V = 540.45 (3) Å³	0.29 × 0.09 × 0.07 mm

Data collection top

Bruker APEXII CCD area-detector diffractometer	3844 independent reflections
Radiation source: sealed tube	3193 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.032
φ and ω scans	θ_max = 32.5°, θ_min = 2.8°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −7→8
T_min = 0.406, T_max = 0.791	k = −11→11
11303 measured reflections	l = −21→21

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)] = 0.032	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.076	H atoms treated by a mixture of independent and constrained refinement
S = 1.08	w = 1/[σ²(F_o²) + (0.0335P)² + 0.2642P] where P = (F_o² + 2F_c²)/3
3844 reflections	(Δ/σ)_max = 0.001
149 parameters	Δρ_max = 0.66 e Å⁻³
0 restraints	Δρ_min = −0.68 e Å⁻³

Crystal data top

C₁₃H₁₀BrNO	γ = 90.086 (2)°
M_r = 276.12	V = 540.45 (3) Å³
Triclinic, P1	Z = 2
a = 5.3552 (2) Å	Mo Kα radiation
b = 7.6334 (2) Å	µ = 3.78 mm⁻¹
c = 13.9956 (5) Å	T = 100 K
α = 105.757 (3)°	0.29 × 0.09 × 0.07 mm
β = 100.585 (3)°

Data collection top

Bruker APEXII CCD area-detector diffractometer	3844 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	3193 reflections with I > 2σ(I)
T_min = 0.406, T_max = 0.791	R_int = 0.032
11303 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.032	0 restraints
wR(F²) = 0.076	H atoms treated by a mixture of independent and constrained refinement
S = 1.08	Δρ_max = 0.66 e Å⁻³
3844 reflections	Δρ_min = −0.68 e Å⁻³
149 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 120.0 (1) K.

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
Br1	0.91443 (4)	0.72493 (3)	0.467544 (14)	0.01790 (7)
O1	1.1259 (3)	0.2407 (2)	0.00304 (11)	0.0175 (3)
N1	0.6913 (3)	0.2128 (2)	−0.03111 (12)	0.0119 (3)
H1N1	0.564 (5)	0.226 (4)	−0.003 (2)	0.020 (6)*
C1	0.9088 (4)	0.3807 (2)	0.13585 (13)	0.0112 (3)
C2	1.1145 (4)	0.3763 (2)	0.21293 (14)	0.0126 (3)
H2A	1.2533	0.3037	0.1972	0.015*
C3	1.1178 (4)	0.4768 (2)	0.31221 (14)	0.0134 (3)
H3A	1.2565	0.4728	0.3646	0.016*
C4	0.9141 (4)	0.5833 (2)	0.33308 (13)	0.0126 (3)
C5	0.7083 (4)	0.5916 (2)	0.25806 (14)	0.0130 (3)
H5A	0.5720	0.6666	0.2739	0.016*
C6	0.7057 (4)	0.4879 (2)	0.15909 (13)	0.0119 (3)
H6A	0.5649	0.4902	0.1072	0.014*
C7	0.9210 (4)	0.2720 (2)	0.03006 (14)	0.0128 (3)
C8	0.6473 (4)	0.1133 (2)	−0.13458 (13)	0.0112 (3)
C9	0.4262 (4)	0.0002 (2)	−0.17278 (14)	0.0124 (3)
H9A	0.3161	−0.0131	−0.1289	0.015*
C10	0.3667 (4)	−0.0932 (2)	−0.27495 (14)	0.0138 (3)
H10A	0.2160	−0.1701	−0.3005	0.017*
C11	0.5252 (4)	−0.0749 (2)	−0.33980 (13)	0.0138 (3)
H11A	0.4832	−0.1381	−0.4097	0.017*
C12	0.7467 (4)	0.0368 (3)	−0.30173 (14)	0.0141 (3)
H12A	0.8567	0.0487	−0.3459	0.017*
C13	0.8091 (4)	0.1317 (2)	−0.19935 (14)	0.0125 (3)
H13A	0.9603	0.2080	−0.1740	0.015*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.02581 (12)	0.01545 (9)	0.01116 (9)	0.00385 (7)	0.00550 (7)	0.00021 (6)
O1	0.0126 (7)	0.0236 (7)	0.0141 (6)	0.0029 (6)	0.0038 (5)	0.0005 (5)
N1	0.0110 (7)	0.0129 (7)	0.0117 (7)	0.0007 (6)	0.0045 (6)	0.0016 (5)
C1	0.0114 (8)	0.0100 (7)	0.0121 (7)	−0.0008 (6)	0.0039 (6)	0.0020 (6)
C2	0.0107 (8)	0.0118 (7)	0.0148 (8)	0.0018 (6)	0.0033 (6)	0.0021 (6)
C3	0.0147 (9)	0.0133 (8)	0.0119 (8)	0.0007 (7)	0.0021 (6)	0.0033 (6)
C4	0.0171 (9)	0.0097 (7)	0.0110 (7)	−0.0002 (7)	0.0057 (6)	0.0010 (6)
C5	0.0142 (9)	0.0108 (7)	0.0148 (8)	0.0022 (7)	0.0063 (7)	0.0027 (6)
C6	0.0125 (8)	0.0111 (7)	0.0116 (7)	0.0014 (6)	0.0026 (6)	0.0021 (6)
C7	0.0136 (9)	0.0127 (8)	0.0121 (8)	0.0021 (7)	0.0029 (6)	0.0034 (6)
C8	0.0135 (8)	0.0090 (7)	0.0115 (7)	0.0028 (6)	0.0031 (6)	0.0031 (6)
C9	0.0115 (8)	0.0109 (7)	0.0154 (8)	0.0017 (6)	0.0042 (6)	0.0037 (6)
C10	0.0116 (9)	0.0129 (8)	0.0159 (8)	0.0007 (7)	0.0019 (7)	0.0030 (6)
C11	0.0148 (9)	0.0131 (8)	0.0109 (7)	0.0027 (7)	0.0015 (6)	−0.0004 (6)
C12	0.0154 (9)	0.0148 (8)	0.0137 (8)	0.0037 (7)	0.0060 (7)	0.0045 (6)
C13	0.0124 (9)	0.0116 (7)	0.0140 (8)	0.0015 (7)	0.0040 (6)	0.0033 (6)

Geometric parameters (Å, º) top

Br1—C4	1.8985 (18)	C5—H5A	0.9500
O1—C7	1.228 (2)	C6—H6A	0.9500
N1—C7	1.361 (2)	C8—C9	1.395 (3)
N1—C8	1.417 (2)	C8—C13	1.396 (3)
N1—H1N1	0.84 (3)	C9—C10	1.390 (3)
C1—C6	1.395 (3)	C9—H9A	0.9500
C1—C2	1.401 (2)	C10—C11	1.384 (3)
C1—C7	1.501 (2)	C10—H10A	0.9500
C2—C3	1.390 (3)	C11—C12	1.391 (3)
C2—H2A	0.9500	C11—H11A	0.9500
C3—C4	1.388 (3)	C12—C13	1.396 (3)
C3—H3A	0.9500	C12—H12A	0.9500
C4—C5	1.390 (3)	C13—H13A	0.9500
C5—C6	1.394 (2)

C7—N1—C8	126.73 (17)	O1—C7—N1	123.92 (17)
C7—N1—H1N1	116.5 (18)	O1—C7—C1	121.13 (17)
C8—N1—H1N1	116.4 (18)	N1—C7—C1	114.94 (16)
C6—C1—C2	119.54 (16)	C9—C8—C13	119.69 (16)
C6—C1—C7	122.67 (16)	C9—C8—N1	117.73 (17)
C2—C1—C7	117.76 (16)	C13—C8—N1	122.50 (17)
C3—C2—C1	120.71 (17)	C10—C9—C8	120.15 (18)
C3—C2—H2A	119.6	C10—C9—H9A	119.9
C1—C2—H2A	119.6	C8—C9—H9A	119.9
C4—C3—C2	118.53 (17)	C11—C10—C9	120.53 (18)
C4—C3—H3A	120.7	C11—C10—H10A	119.7
C2—C3—H3A	120.7	C9—C10—H10A	119.7
C3—C4—C5	122.06 (17)	C10—C11—C12	119.40 (17)
C3—C4—Br1	119.66 (14)	C10—C11—H11A	120.3
C5—C4—Br1	118.28 (14)	C12—C11—H11A	120.3
C4—C5—C6	118.79 (17)	C11—C12—C13	120.79 (18)
C4—C5—H5A	120.6	C11—C12—H12A	119.6
C6—C5—H5A	120.6	C13—C12—H12A	119.6
C5—C6—C1	120.35 (17)	C8—C13—C12	119.43 (17)
C5—C6—H6A	119.8	C8—C13—H13A	120.3
C1—C6—H6A	119.8	C12—C13—H13A	120.3

C6—C1—C2—C3	0.2 (3)	C2—C1—C7—O1	−28.1 (3)
C7—C1—C2—C3	178.64 (17)	C6—C1—C7—N1	−29.9 (3)
C1—C2—C3—C4	−0.7 (3)	C2—C1—C7—N1	151.72 (17)
C2—C3—C4—C5	0.1 (3)	C7—N1—C8—C9	153.01 (18)
C2—C3—C4—Br1	−179.15 (14)	C7—N1—C8—C13	−30.2 (3)
C3—C4—C5—C6	0.8 (3)	C13—C8—C9—C10	−0.3 (3)
Br1—C4—C5—C6	−179.88 (14)	N1—C8—C9—C10	176.59 (16)
C4—C5—C6—C1	−1.3 (3)	C8—C9—C10—C11	−0.1 (3)
C2—C1—C6—C5	0.7 (3)	C9—C10—C11—C12	0.5 (3)
C7—C1—C6—C5	−177.57 (17)	C10—C11—C12—C13	−0.6 (3)
C8—N1—C7—O1	−2.4 (3)	C9—C8—C13—C12	0.2 (3)
C8—N1—C7—C1	177.82 (16)	N1—C8—C13—C12	−176.50 (16)
C6—C1—C7—O1	150.22 (19)	C11—C12—C13—C8	0.2 (3)

Hydrogen-bond geometry (Å, º) top

Cg1 and Cg2 are the centroids of the C1–C6 and C8–C13 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N1···O1ⁱ	0.84 (3)	2.37 (3)	3.150 (2)	156 (2)
C13—H13A···O1	0.95	2.42	2.923 (2)	113
C2—H2A···Cg2ⁱⁱ	0.95	2.77	3.4855 (19)	132
C5—H5A···Cg2ⁱⁱⁱ	0.95	2.70	3.4258 (19)	134
C10—H10A···Cg1^iv	0.95	2.90	3.5444 (19)	126
C13—H13A···Cg1^v	0.95	2.84	3.4950 (19)	127

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

Experimental details

Crystal data
Chemical formula	C₁₃H₁₀BrNO
M_r	276.12
Crystal system, space group	Triclinic, P1
Temperature (K)	100
a, b, c (Å)	5.3552 (2), 7.6334 (2), 13.9956 (5)
α, β, γ (°)	105.757 (3), 100.585 (3), 90.086 (2)
V (Å³)	540.45 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	3.78
Crystal size (mm)	0.29 × 0.09 × 0.07

Data collection
Diffractometer	Bruker APEXII CCD area-detector
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.406, 0.791
No. of measured, independent and observed [I > 2σ(I)] reflections	11303, 3844, 3193
R_int	0.032
(sin θ/λ)_max (Å⁻¹)	0.756

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.032, 0.076, 1.08
No. of reflections	3844
No. of parameters	149
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.66, −0.68

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

Cg1 and Cg2 are the centroids of the C1–C6 and C8–C13 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N1···O1ⁱ	0.84 (3)	2.37 (3)	3.150 (2)	156 (2)
C2—H2A···Cg2ⁱⁱ	0.95	2.77	3.4855 (19)	132
C5—H5A···Cg2ⁱⁱⁱ	0.95	2.70	3.4258 (19)	134
C10—H10A···Cg1^iv	0.95	2.90	3.5444 (19)	126
C13—H13A···Cg1^v	0.95	2.84	3.4950 (19)	127

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

Footnotes

‡Thomson Reuters ResearcherID: A-3561-2009.

§Thomson Reuters ResearcherID: A-5085-2009. Additional correspondence author, e-mail: suchada.c@psu.ac.th.

Acknowledgements

The authors thank Prince of Songkla University for financial support through the Crystal Materials Research Unit. NB also thanks Prince of Songkla University for a postdoctoral fellowship. The authors also thank Universiti Sains Malaysia for the Research University Grant No. 1001/PFIZIK/811160.

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Volume 68| Part 4| April 2012| Pages o1269-o1270

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