2-Amino­pyridinium (2-amino­pyridine)trichloridonickelate(II)

Fun, H.-K.; Franklin, S.; Jebas, S.R.; Balasubramanian, T.

doi:10.1107/S1600536808005655

metal-organic compounds

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ISSN: 2056-9890

Volume 64| Part 4| April 2008| Pages m520-m521

doi:10.1107/S1600536808005655

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2-Aminopyridinium (2-aminopyridine)trichloridonickelate(II)

Hoong-Kun Fun,^a ^* S. Franklin,^b Samuel Robinson Jebas ^a ‡ and T. Balasubramanian ^b

^aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and ^bDepartment of Physics, National Institute of Technology, Tiruchirappalli 620 015, India
^*Correspondence e-mail: hkfun@usm.my

(Received 21 February 2008; accepted 28 February 2008; online 5 March 2008)

In the title compound, (C₅H₇N₂)[NiCl₃(C₅H₆N₂)], the Ni^II atom is four-coordinated by three chloride anions and one N atom of a 2-aminopyridine ligand, forming a distorted tetrahedral coordination. In the crystal structure, cations and complex anions are linked into chains along the a, b and c axes by N—H⋯Cl hydrogen bonds, leading to the formation of a three-dimensional framework.

Related literature

For related literature, see: Batsanov & Howard (2001 ); Bis & Zaworotko (2005 ); Chao et al. (1975 ); Corain et al. (1985 ); Jebas et al. (2006 ); Valdés-Martínez et al. (2001 ); Sletten & Kovacs (1993 ); Smith et al. (2000 , 2001 ); Stibrany et al. (2004 ); Wei & Willett (1995 ); Windholz (1976 ).

Experimental

Crystal data

(C₅H₇N₂)[NiCl₃(C₅H₆N₂)]
M_r = 354.3
Monoclinic, C c
a = 12.9265 (1) Å
b = 8.0644 (1) Å
c = 13.9893 (1) Å
β = 106.163 (1)°
V = 1400.67 (2) Å³
Z = 4
Mo Kα radiation
μ = 1.94 mm⁻¹
T = 100.0 (1) K
0.37 × 0.08 × 0.07 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer with Oxford Cryosystems Cobra low-temperature attachment
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.533, T_max = 0.876
19539 measured reflections
6427 independent reflections
5088 reflections with I > 2σ(I)
R_int = 0.031

Refinement

R[F² > 2σ(F²)] = 0.035
wR(F²) = 0.079
S = 1.05
6427 reflections
167 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.52 e Å⁻³
Δρ_min = −0.64 e Å⁻³
Absolute structure: Flack (1983 ), 1953 Friedel pairs
Flack parameter: 0.065 (9)

Table 1
Selected geometric parameters (Å, °)

Ni1—N1	2.0287 (17)
Ni1—Cl2	2.2625 (6)
Ni1—Cl1	2.2665 (5)
Ni1—Cl3	2.2722 (6)

N1—Ni1—Cl2	114.10 (5)
N1—Ni1—Cl1	109.21 (5)
Cl2—Ni1—Cl1	107.77 (2)
N1—Ni1—Cl3	104.63 (5)
Cl2—Ni1—Cl3	108.62 (2)
Cl1—Ni1—Cl3	112.60 (2)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H1N3⋯Cl2ⁱ	0.82 (3)	2.81 (3)	3.380 (2)	128 (2)
N2—H2B⋯Cl2	0.86	2.53	3.3475 (19)	159
N2—H2C⋯Cl1ⁱⁱ	0.86	2.63	3.4866 (19)	172
N4—H4B⋯Cl3ⁱ	0.86	2.36	3.197 (2)	165
N4—H4C⋯Cl1ⁱⁱⁱ	0.86	2.54	3.344 (2)	156
Symmetry codes: (i) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (ii) $[x, -y+1, z+{\script{1\over 2}}]$ ; (iii) x, y-1, z.

Data collection: APEX2 (Bruker, 2005); cell refinement: APEX2; data reduction: SAINT (Bruker, 2005); 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, 2003 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808005655/ci2566sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808005655/ci2566Isup2.hkl

checkCIF report

Comment top

2-Aminopyridine is used in the manufacture of pharmaceuticals, especially antihistaminic drugs (Windholz, 1976). As a part of our investigations on the binding modes of 2-aminopyridine with metals, we report here the crystal structure of 2-aminopyridinium (2-aminopyridine)trichloronickel(II).

The asymmetric unit of the title compound contains one 2-aminopyridinium cation and one (2-aminopyridine)trichloronickel(II) anion. Protonation of atom N3 of the uncomplexed 2-aminopyridine results in the widening of the C6—N3—C10 angle to 123.3 (2)°, which is 117.7 (1)° in neutral 2-aminopyridine (Chao et al., 1975). The bond lengths and angles are comparable with those observed in related structures (Bis & Zaworotko, 2005; Smith et al., 2000; Jebas et al., 2006).

In the monomeric complex, the Ni^II ion is four-coordinated by three Cl anions and the N atom of the 2-aminopyridine ligand, forming a distorted tetrahedral coordination (Fig 1). The Ni—Cl bond lengths (Table 1) are comparable with that reported in the literature (Valdés-Martínez et al., 2001; Batsanov et al., 2001; Sletten & Kovacs, 1993; Corain et al., 1985; Stibrany et al., 2004). The Cl—Ni—Cl bond angles (107.77 (2)° and 108.62 (2)°) are close to the values reported in the literature (Smith et al., 2001; Wei et al., 1995). The dihedral angle between the pyridine and pyridinium rings is 0.9 (2)°.

In the crystal structure, the cations and anionic complexes are stacked into chains along the a, b and c axes and are linked into a three-dimensional framework by N—H···Cl hydrogen bonds (Fig 2).

Related literature top

For related literature, see: Batsanov & Howard (2001); Bis & Zaworotko (2005); Chao et al. (1975); Corain et al. (1985); Jebas et al. (2006); Valdés-Martínez et al. (2001); Sletten & Kovacs (1993); Smith et al. (2000, 2001); Stibrany et al. (2004); Wei & Willett (1995); Windholz (1976).

Experimental top

Solutions of 2-aminopyridine and NiCl₂.2H₂O in water were mixed in a molar ratio of 2:1. Few drops of dilute hydrochloric acid were added to the solution and heated at 363 K for 2 h. Blue crystals of the title compound were obtained by slow evaporation after a period of one week.

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: APEX2 (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, 2003).

Figures top

	Fig. 1. The asymmetric unit of the title compound, showing 50% probability displacement ellipsoids and the atomic numbering.
	Fig. 2. The crystal packing of the title compound, viewed along the b axis. Hydrogen bonds are shown as dashed lines.

2-Aminopyridinium (2-aminopyridine)trichloridonickelate(II) top

Crystal data top

(C₅H₇N₂)[NiCl₃(C₅H₆N₂)]	F(000) = 720
M_r = 354.3	D_x = 1.68 Mg m⁻³
Monoclinic, Cc	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C -2yc	Cell parameters from 8411 reflections
a = 12.9265 (1) Å	θ = 3.0–30.6°
b = 8.0644 (1) Å	µ = 1.94 mm⁻¹
c = 13.9893 (1) Å	T = 100 K
β = 106.163 (1)°	Block, blue
V = 1400.67 (2) Å³	0.37 × 0.08 × 0.07 mm
Z = 4

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	5088 reflections with I > 2σ(I)
Detector resolution: 8.33 pixels mm^-1	R_int = 0.031
ω scans	θ_max = 40.6°, θ_min = 3.0°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −23→23
T_min = 0.533, T_max = 0.876	k = −14→14
19539 measured reflections	l = −25→16
6427 independent reflections

Refinement top

Refinement on F²	H atoms treated by a mixture of independent and constrained refinement
Least-squares matrix: full	w = 1/[σ²(F_o²) + (0.034P)²] where P = (F_o² + 2F_c²)/3
R[F² > 2σ(F²)] = 0.035	(Δ/σ)_max < 0.001
wR(F²) = 0.079	Δρ_max = 0.52 e Å⁻³
S = 1.05	Δρ_min = −0.64 e Å⁻³
6427 reflections	Absolute structure: Flack (1983), 1953 Friedel pairs
167 parameters	Absolute structure parameter: 0.065 (9)
2 restraints

Crystal data top

(C₅H₇N₂)[NiCl₃(C₅H₆N₂)]	V = 1400.67 (2) Å³
M_r = 354.3	Z = 4
Monoclinic, Cc	Mo Kα radiation
a = 12.9265 (1) Å	µ = 1.94 mm⁻¹
b = 8.0644 (1) Å	T = 100 K
c = 13.9893 (1) Å	0.37 × 0.08 × 0.07 mm
β = 106.163 (1)°

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	6427 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	5088 reflections with I > 2σ(I)
T_min = 0.533, T_max = 0.876	R_int = 0.031
19539 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.035	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.079	Δρ_max = 0.52 e Å⁻³
S = 1.05	Δρ_min = −0.64 e Å⁻³
6427 reflections	Absolute structure: Flack (1983), 1953 Friedel pairs
167 parameters	Absolute structure parameter: 0.065 (9)
2 restraints

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Ni1	0.245028 (18)	0.65589 (3)	0.188212 (18)	0.01865 (6)
Cl1	0.40142 (4)	0.66552 (7)	0.14504 (4)	0.01889 (9)
Cl2	0.19741 (4)	0.38637 (6)	0.19116 (4)	0.02255 (10)
Cl3	0.10912 (4)	0.79387 (7)	0.07906 (4)	0.02299 (10)
N1	0.26459 (13)	0.7760 (2)	0.31947 (12)	0.0157 (3)
N2	0.30301 (15)	0.5422 (2)	0.41934 (14)	0.0228 (4)
H2B	0.2895	0.4816	0.3667	0.027*
H2C	0.322	0.4966	0.4772	0.027*
N3	0.55299 (14)	0.0900 (2)	0.44965 (14)	0.0191 (3)
N4	0.53731 (16)	−0.1509 (2)	0.35719 (15)	0.0228 (4)
H4B	0.5574	−0.2072	0.4114	0.027*
H4C	0.5224	−0.2007	0.3006	0.027*
C1	0.29457 (15)	0.7074 (3)	0.41122 (15)	0.0181 (4)
C2	0.31669 (17)	0.8074 (3)	0.49792 (16)	0.0213 (4)
H2A	0.3384	0.7591	0.5607	0.026*
C3	0.30568 (17)	0.9761 (3)	0.48792 (18)	0.0254 (4)
H3A	0.3199	1.0431	0.5442	0.03*
C4	0.27352 (17)	1.0463 (3)	0.39438 (18)	0.0245 (4)
H4A	0.2652	1.1605	0.3867	0.029*
C5	0.25411 (16)	0.9441 (3)	0.31322 (17)	0.0198 (4)
H5A	0.2326	0.992	0.2503	0.024*
C6	0.52944 (15)	0.0123 (2)	0.36071 (15)	0.0173 (3)
C7	0.49768 (16)	0.1116 (3)	0.27449 (16)	0.0203 (4)
H7A	0.4813	0.0628	0.2118	0.024*
C8	0.49108 (16)	0.2795 (3)	0.28322 (16)	0.0217 (4)
H8A	0.4704	0.3447	0.2262	0.026*
C9	0.51508 (17)	0.3550 (3)	0.37731 (18)	0.0229 (4)
H9A	0.5093	0.4693	0.3832	0.027*
C10	0.54691 (16)	0.2575 (3)	0.45963 (17)	0.0222 (4)
H10A	0.5645	0.3051	0.5227	0.027*
H1N3	0.571 (2)	0.030 (3)	0.499 (2)	0.023 (7)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ni1	0.02016 (11)	0.02167 (12)	0.01419 (12)	−0.00140 (10)	0.00489 (9)	−0.00168 (10)
Cl1	0.0188 (2)	0.0211 (2)	0.0179 (2)	−0.00022 (15)	0.00699 (18)	−0.00025 (16)
Cl2	0.0285 (2)	0.0194 (2)	0.0211 (2)	−0.00610 (19)	0.0092 (2)	−0.00511 (18)
Cl3	0.0208 (2)	0.0324 (3)	0.0142 (2)	0.00279 (19)	0.00214 (17)	0.00196 (19)
N1	0.0151 (7)	0.0181 (7)	0.0133 (7)	−0.0002 (6)	0.0030 (6)	0.0000 (6)
N2	0.0313 (9)	0.0201 (9)	0.0150 (8)	0.0021 (7)	0.0032 (7)	0.0003 (6)
N3	0.0170 (7)	0.0273 (9)	0.0132 (8)	0.0013 (6)	0.0043 (6)	0.0020 (7)
N4	0.0283 (9)	0.0220 (8)	0.0168 (9)	−0.0019 (7)	0.0038 (7)	0.0029 (6)
C1	0.0146 (8)	0.0238 (10)	0.0165 (9)	0.0012 (6)	0.0053 (7)	0.0011 (7)
C2	0.0180 (8)	0.0307 (11)	0.0149 (9)	−0.0009 (7)	0.0043 (7)	−0.0018 (8)
C3	0.0224 (9)	0.0269 (11)	0.0278 (12)	−0.0030 (8)	0.0087 (9)	−0.0105 (9)
C4	0.0251 (10)	0.0189 (9)	0.0309 (12)	−0.0026 (8)	0.0099 (9)	−0.0067 (9)
C5	0.0195 (8)	0.0179 (9)	0.0224 (10)	−0.0007 (7)	0.0065 (8)	−0.0002 (8)
C6	0.0153 (8)	0.0220 (9)	0.0142 (9)	−0.0021 (7)	0.0035 (7)	0.0011 (7)
C7	0.0183 (8)	0.0269 (10)	0.0145 (9)	0.0001 (7)	0.0023 (7)	0.0026 (8)
C8	0.0201 (9)	0.0261 (10)	0.0185 (10)	0.0034 (8)	0.0050 (8)	0.0059 (8)
C9	0.0204 (9)	0.0225 (10)	0.0272 (12)	0.0019 (7)	0.0092 (9)	−0.0010 (8)
C10	0.0183 (8)	0.0288 (11)	0.0200 (10)	0.0008 (8)	0.0062 (8)	−0.0052 (8)

Geometric parameters (Å, º) top

Ni1—N1	2.0287 (17)	C2—C3	1.371 (3)
Ni1—Cl2	2.2625 (6)	C2—H2A	0.93
Ni1—Cl1	2.2665 (5)	C3—C4	1.380 (3)
Ni1—Cl3	2.2722 (6)	C3—H3A	0.93
N1—C1	1.352 (3)	C4—C5	1.369 (3)
N1—C5	1.363 (3)	C4—H4A	0.93
N2—C1	1.339 (3)	C5—H5A	0.93
N2—H2B	0.86	C6—C7	1.410 (3)
N2—H2C	0.86	C7—C8	1.364 (3)
N3—C6	1.350 (3)	C7—H7A	0.93
N3—C10	1.362 (3)	C8—C9	1.404 (3)
N3—H1N3	0.82 (3)	C8—H8A	0.93
N4—C6	1.322 (3)	C9—C10	1.360 (3)
N4—H4B	0.86	C9—H9A	0.93
N4—H4C	0.86	C10—H10A	0.93
C1—C2	1.417 (3)

N1—Ni1—Cl2	114.10 (5)	C2—C3—C4	120.0 (2)
N1—Ni1—Cl1	109.21 (5)	C2—C3—H3A	120
Cl2—Ni1—Cl1	107.77 (2)	C4—C3—H3A	120
N1—Ni1—Cl3	104.63 (5)	C5—C4—C3	118.5 (2)
Cl2—Ni1—Cl3	108.62 (2)	C5—C4—H4A	120.8
Cl1—Ni1—Cl3	112.60 (2)	C3—C4—H4A	120.8
C1—N1—C5	117.72 (18)	N1—C5—C4	123.6 (2)
C1—N1—Ni1	126.48 (14)	N1—C5—H5A	118.2
C5—N1—Ni1	115.59 (13)	C4—C5—H5A	118.2
C1—N2—H2B	120	N4—C6—N3	119.8 (2)
C1—N2—H2C	120	N4—C6—C7	122.7 (2)
H2B—N2—H2C	120	N3—C6—C7	117.51 (19)
C6—N3—C10	123.36 (19)	C8—C7—C6	119.8 (2)
C6—N3—H1N3	115.9 (18)	C8—C7—H7A	120.1
C10—N3—H1N3	120.7 (18)	C6—C7—H7A	120.1
C6—N4—H4B	120	C7—C8—C9	120.7 (2)
C6—N4—H4C	120	C7—C8—H8A	119.6
H4B—N4—H4C	120	C9—C8—H8A	119.6
N2—C1—N1	118.88 (18)	C10—C9—C8	118.6 (2)
N2—C1—C2	120.05 (19)	C10—C9—H9A	120.7
N1—C1—C2	121.1 (2)	C8—C9—H9A	120.7
C3—C2—C1	119.1 (2)	C9—C10—N3	119.9 (2)
C3—C2—H2A	120.4	C9—C10—H10A	120
C1—C2—H2A	120.4	N3—C10—H10A	120

Cl2—Ni1—N1—C1	28.37 (17)	C2—C3—C4—C5	−0.5 (3)
Cl1—Ni1—N1—C1	−92.28 (15)	C1—N1—C5—C4	0.8 (3)
Cl3—Ni1—N1—C1	146.95 (15)	Ni1—N1—C5—C4	−174.29 (16)
Cl2—Ni1—N1—C5	−156.98 (11)	C3—C4—C5—N1	0.1 (3)
Cl1—Ni1—N1—C5	82.36 (13)	C10—N3—C6—N4	179.99 (18)
Cl3—Ni1—N1—C5	−38.41 (13)	C10—N3—C6—C7	0.4 (3)
C5—N1—C1—N2	178.47 (16)	N4—C6—C7—C8	179.96 (19)
Ni1—N1—C1—N2	−7.0 (3)	N3—C6—C7—C8	−0.5 (3)
C5—N1—C1—C2	−1.4 (3)	C6—C7—C8—C9	−0.3 (3)
Ni1—N1—C1—C2	173.14 (13)	C7—C8—C9—C10	1.1 (3)
N2—C1—C2—C3	−178.84 (18)	C8—C9—C10—N3	−1.2 (3)
N1—C1—C2—C3	1.0 (3)	C6—N3—C10—C9	0.5 (3)
C1—C2—C3—C4	0.0 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H1N3···Cl2ⁱ	0.82 (3)	2.81 (3)	3.380 (2)	128 (2)
N2—H2B···Cl2	0.86	2.53	3.3475 (19)	159
N2—H2C···Cl1ⁱⁱ	0.86	2.63	3.4866 (19)	172
N4—H4B···Cl3ⁱ	0.86	2.36	3.197 (2)	165
N4—H4C···Cl1ⁱⁱⁱ	0.86	2.54	3.344 (2)	156

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

Experimental details

Crystal data
Chemical formula	(C₅H₇N₂)[NiCl₃(C₅H₆N₂)]
M_r	354.3
Crystal system, space group	Monoclinic, Cc
Temperature (K)	100
a, b, c (Å)	12.9265 (1), 8.0644 (1), 13.9893 (1)
β (°)	106.163 (1)
V (Å³)	1400.67 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.94
Crystal size (mm)	0.37 × 0.08 × 0.07

Data collection
Diffractometer	Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.533, 0.876
No. of measured, independent and observed [I > 2σ(I)] reflections	19539, 6427, 5088
R_int	0.031
(sin θ/λ)_max (Å⁻¹)	0.916

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.035, 0.079, 1.05
No. of reflections	6427
No. of parameters	167
No. of restraints	2
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.52, −0.64
Absolute structure	Flack (1983), 1953 Friedel pairs
Absolute structure parameter	0.065 (9)

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2003).

Selected geometric parameters (Å, º) top

Ni1—N1	2.0287 (17)	Ni1—Cl1	2.2665 (5)
Ni1—Cl2	2.2625 (6)	Ni1—Cl3	2.2722 (6)

N1—Ni1—Cl2	114.10 (5)	N1—Ni1—Cl3	104.63 (5)
N1—Ni1—Cl1	109.21 (5)	Cl2—Ni1—Cl3	108.62 (2)
Cl2—Ni1—Cl1	107.77 (2)	Cl1—Ni1—Cl3	112.60 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H1N3···Cl2ⁱ	0.82 (3)	2.81 (3)	3.380 (2)	128 (2)
N2—H2B···Cl2	0.86	2.53	3.3475 (19)	159
N2—H2C···Cl1ⁱⁱ	0.86	2.63	3.4866 (19)	172
N4—H4B···Cl3ⁱ	0.86	2.36	3.197 (2)	165
N4—H4C···Cl1ⁱⁱⁱ	0.86	2.54	3.344 (2)	156

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

Footnotes

‡Permanent address: Lecturer, Department of Physics, Karunya University, Karunya Nagar, Coimbatore 641 114, India.

Acknowledgements

HKF and SRJ thank the Malaysian Government and Universiti Sains Malaysia for the Science Fund grant No. 305/PFIZIK/613312. SRJ thanks Universiti Sains Malaysia for the award a postdoctoral research fellowship.

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