{2-Morpholino-N-[1-(2-pyrid­yl)ethyl­idene]ethanamine-κ3N,N′,N′′}bis­(thio­cyanato-κN)copper(II)

Suleiman Gwaram, N.; Ikmal Hisham, N.A.; Khaledi, H.; Mohd Ali, H.

doi:10.1107/S1600536810050889

metal-organic compounds

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ISSN: 2056-9890

Volume 67| Part 1| January 2011| Page m58

https://doi.org/10.1107/S1600536810050889

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{2-Morpholino-N-[1-(2-pyridyl)ethylidene]ethanamine-κ³N,N′,N′′}bis(thiocyanato-κN)copper(II)

Nura Suleiman Gwaram,^a Nurul Azimah Ikmal Hisham,^a Hamid Khaledi ^a ^* and Hapipah Mohd Ali ^a

^aDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: khaledi@siswa.um.edu.my

(Received 1 December 2010; accepted 4 December 2010; online 11 December 2010)

In the title compound, [Cu(NCS)₂(C₁₃H₁₉N₃O)], the Cu^II ion is five-coordinated by the N,N′,N′′-tridentate Schiff base and the N atoms of two isothiocyanate ligands in a square-pyramidal geometry. In the crystal, C—H⋯N, C—H⋯O and C—H⋯S interactions link adjacent molecules into layers parallel to the ac plane. A weak intermolecular π–π interaction occurs between the aromatic rings with a centroid–centroid distance of 3.9412 (9) Å.

Related literature

For related structures of Cu(II) complexes, see: Drew et al. (2009 ); You et al. (2006 ); Yue et al. (2005 ).

Experimental

Crystal data

[Cu(NCS)₂(C₁₃H₁₉N₃O)]
M_r = 413.01
Monoclinic, P 2₁ /c
a = 10.6912 (1) Å
b = 14.0350 (2) Å
c = 12.2530 (2) Å
β = 92.203 (1)°
V = 1837.22 (4) Å³
Z = 4
Mo Kα radiation
μ = 1.43 mm⁻¹
T = 100 K
0.41 × 0.39 × 0.08 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.592, T_max = 0.894
16491 measured reflections
4007 independent reflections
3593 reflections with I > 2σ(I)
R_int = 0.024

Refinement

R[F² > 2σ(F²)] = 0.023
wR(F²) = 0.061
S = 1.08
4007 reflections
218 parameters
2 restraints
H-atom parameters constrained
Δρ_max = 0.37 e Å⁻³
Δρ_min = −0.26 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4—H4⋯O1ⁱ	0.95	2.40	3.211 (2)	144
C7—H7B⋯O1ⁱ	0.98	2.33	3.248 (2)	155
C7—H7C⋯S2ⁱⁱ	0.98	2.83	3.7021 (18)	149
C8—H8B⋯N5ⁱⁱ	0.99	2.55	3.367 (2)	140
C13—H13A⋯N4	0.99	2.58	3.181 (2)	119
Symmetry codes: (i) x+1, y, z; (ii) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001 ); software used to prepare material for publication: SHELXL97 and publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536810050889/is2639sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810050889/is2639Isup2.hkl

checkCIF report

Comment top

The title compound is a mixed-ligand copper(II) complex with isothiocyanate and the Schiff base 2-morpholino-N-[1-(2-pyridyl)ethylidene]ethanamine. The geometry of the complex is slightly distorted square-pyramidal (τ = 0.05) with the N,N',N"-tridentate Schiff base and one SCN ligand at the basal positions, while the apical position is occupied by a second SCN ligand. This arrangement has been observed in some other mixed-ligand copper(II) complexes (Drew et al., 2009; You et al., 2006; Yue et al., 2005). In the crystal structure, the C—H···N, C—H···O and C—H···S interactions within the range for normal hydrogen bonds link the adjacent molecules into layers parallel to the ac plane (Fig. 2). An intramolecular C—H···N hydrogen bonding is also observed. Moreover, the aromatic rings of each two molecules related by the symmetry -x + 2, -y, -z + 1, are arranged in an antiparallel manner with centroid-centroid separation of 3.9412 (9) Å, indicative of a weak π–π interaction.

Related literature top

For related structures of Cu(II) complexes, see: Drew et al. (2009); You et al. (2006); Yue et al. (2005).

Experimental top

A mixture of 2-acetylpyridine (0.20 g, 1.65 mmol) and 4-(2-aminoethyl)morpholine (0.21 g, 1.65 mmol) in ethanol (20 ml) was refluxed for 2 hr followed by addition of a solution of copper(II) acetate monohydrate (0.33 g, 1.65 mmol) and sodium thiocyanete (0.134 g, 1.65 mmol) in a minimum amount of ethanol. The resulting solution was refluxed for 30 min, then left at room temperature. The crystals of the title complex were obtained in a week.

Structure description top

For related structures of Cu(II) complexes, see: Drew et al. (2009); You et al. (2006); Yue et al. (2005).

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and publCIF (Westrip, 2010).

Figures top

	Fig. 1. Thermal ellipsoid plot of the title compound at the 50% probability level. Hydrogen atoms are drawn as spheres of arbitrary radii.
	Fig. 2. The packing diagram of the title compound, viewed down the crystallographic a axis.

{2-Morpholino-N-[1-(2-pyridyl)ethylidene]ethanamine-κ³N,N',N''}bis(thiocyanato-κN)copper(II) top

Crystal data top

[Cu(NCS)₂(C₁₃H₁₉N₃O)]	F(000) = 852
M_r = 413.01	D_x = 1.493 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 7443 reflections
a = 10.6912 (1) Å	θ = 2.2–30.7°
b = 14.0350 (2) Å	µ = 1.43 mm⁻¹
c = 12.2530 (2) Å	T = 100 K
β = 92.203 (1)°	Plate, blue
V = 1837.22 (4) Å³	0.41 × 0.39 × 0.08 mm
Z = 4

Data collection top

Bruker APEXII CCD diffractometer	4007 independent reflections
Radiation source: fine-focus sealed tube	3593 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.024
φ and ω scans	θ_max = 27.0°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −13→13
T_min = 0.592, T_max = 0.894	k = −17→17
16491 measured reflections	l = −15→15

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)] = 0.023	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.061	H-atom parameters constrained
S = 1.08	w = 1/[σ²(F_o²) + (0.0264P)² + 0.8835P] where P = (F_o² + 2F_c²)/3
4007 reflections	(Δ/σ)_max = 0.001
218 parameters	Δρ_max = 0.37 e Å⁻³
2 restraints	Δρ_min = −0.26 e Å⁻³

Crystal data top

[Cu(NCS)₂(C₁₃H₁₉N₃O)]	V = 1837.22 (4) Å³
M_r = 413.01	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 10.6912 (1) Å	µ = 1.43 mm⁻¹
b = 14.0350 (2) Å	T = 100 K
c = 12.2530 (2) Å	0.41 × 0.39 × 0.08 mm
β = 92.203 (1)°

Data collection top

Bruker APEXII CCD diffractometer	4007 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3593 reflections with I > 2σ(I)
T_min = 0.592, T_max = 0.894	R_int = 0.024
16491 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.023	2 restraints
wR(F²) = 0.061	H-atom parameters constrained
S = 1.08	Δρ_max = 0.37 e Å⁻³
4007 reflections	Δρ_min = −0.26 e Å⁻³
218 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
Cu1	0.828576 (17)	0.205404 (13)	0.447661 (15)	0.01426 (6)
S1	0.54717 (4)	−0.02085 (3)	0.29655 (4)	0.02655 (11)
S2	1.11219 (4)	0.39163 (3)	0.33440 (4)	0.02849 (11)
O1	0.42152 (11)	0.29240 (8)	0.55167 (10)	0.0219 (3)
N1	0.99124 (12)	0.13295 (9)	0.43945 (10)	0.0152 (3)
N2	0.92988 (12)	0.27488 (9)	0.55693 (10)	0.0153 (3)
N3	0.68518 (12)	0.28625 (9)	0.50715 (11)	0.0155 (3)
N4	0.72317 (13)	0.11286 (10)	0.37153 (11)	0.0194 (3)
N5	0.87234 (14)	0.31121 (10)	0.31479 (11)	0.0212 (3)
C1	1.01523 (15)	0.05728 (11)	0.37750 (12)	0.0176 (3)
H1	0.9486	0.0289	0.3355	0.021*
C2	1.13462 (16)	0.01887 (12)	0.37269 (13)	0.0204 (3)
H2	1.1497	−0.0345	0.3273	0.024*
C3	1.23136 (16)	0.05957 (12)	0.43502 (14)	0.0216 (3)
H3	1.3138	0.0346	0.4328	0.026*
C4	1.20628 (15)	0.13735 (12)	0.50084 (13)	0.0200 (3)
H4	1.2711	0.1659	0.5449	0.024*
C5	1.08541 (15)	0.17262 (11)	0.50118 (12)	0.0163 (3)
C6	1.04657 (15)	0.25572 (11)	0.56749 (12)	0.0166 (3)
C7	1.13919 (16)	0.30782 (13)	0.63899 (14)	0.0233 (4)
H7A	1.1033	0.3688	0.6612	0.035*
H7B	1.2152	0.3196	0.5989	0.035*
H7C	1.1600	0.2694	0.7040	0.035*
C8	0.86732 (15)	0.35203 (11)	0.61333 (13)	0.0182 (3)
H8A	0.9224	0.4087	0.6188	0.022*
H8B	0.8471	0.3318	0.6880	0.022*
C9	0.74783 (15)	0.37566 (11)	0.54728 (13)	0.0184 (3)
H9A	0.6903	0.4117	0.5934	0.022*
H9B	0.7681	0.4163	0.4843	0.022*
C10	0.62870 (15)	0.23026 (11)	0.59640 (13)	0.0178 (3)
H10A	0.6913	0.2230	0.6575	0.021*
H10B	0.6070	0.1658	0.5688	0.021*
C11	0.51185 (15)	0.27710 (12)	0.63883 (13)	0.0204 (3)
H11A	0.4754	0.2359	0.6949	0.024*
H11B	0.5344	0.3388	0.6734	0.024*
C12	0.47049 (16)	0.35294 (12)	0.47023 (14)	0.0223 (3)
H12A	0.4932	0.4154	0.5029	0.027*
H12B	0.4059	0.3637	0.4115	0.027*
C13	0.58532 (15)	0.30782 (12)	0.42254 (13)	0.0191 (3)
H13A	0.5604	0.2481	0.3847	0.023*
H13B	0.6193	0.3515	0.3676	0.023*
C14	0.65038 (15)	0.05637 (11)	0.34076 (12)	0.0165 (3)
C15	0.97181 (16)	0.34563 (11)	0.32179 (13)	0.0190 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cu1	0.01509 (10)	0.01341 (10)	0.01417 (10)	−0.00117 (7)	−0.00099 (7)	−0.00142 (7)
S1	0.0282 (2)	0.0203 (2)	0.0307 (2)	−0.00934 (17)	−0.00451 (18)	−0.00294 (18)
S2	0.0273 (2)	0.0211 (2)	0.0369 (3)	−0.00521 (17)	−0.00168 (19)	0.00639 (19)
O1	0.0166 (6)	0.0241 (6)	0.0251 (6)	−0.0018 (5)	0.0010 (5)	0.0008 (5)
N1	0.0182 (7)	0.0140 (6)	0.0135 (6)	−0.0012 (5)	0.0005 (5)	0.0014 (5)
N2	0.0179 (7)	0.0143 (6)	0.0137 (6)	−0.0018 (5)	0.0007 (5)	−0.0003 (5)
N3	0.0163 (7)	0.0152 (6)	0.0150 (6)	−0.0016 (5)	−0.0008 (5)	0.0012 (5)
N4	0.0196 (7)	0.0183 (7)	0.0200 (7)	−0.0007 (5)	−0.0014 (5)	−0.0012 (6)
N5	0.0269 (8)	0.0199 (7)	0.0167 (7)	0.0000 (6)	0.0007 (6)	0.0027 (5)
C1	0.0235 (8)	0.0150 (7)	0.0141 (7)	−0.0014 (6)	−0.0007 (6)	0.0014 (6)
C2	0.0271 (9)	0.0164 (8)	0.0178 (8)	0.0031 (6)	0.0014 (6)	−0.0001 (6)
C3	0.0210 (8)	0.0202 (8)	0.0236 (8)	0.0032 (6)	0.0017 (7)	0.0033 (7)
C4	0.0182 (8)	0.0205 (8)	0.0212 (8)	−0.0008 (6)	−0.0016 (6)	0.0011 (7)
C5	0.0186 (8)	0.0162 (7)	0.0142 (7)	−0.0019 (6)	0.0007 (6)	0.0013 (6)
C6	0.0197 (8)	0.0168 (7)	0.0134 (7)	−0.0025 (6)	0.0013 (6)	−0.0003 (6)
C7	0.0183 (8)	0.0284 (9)	0.0231 (8)	−0.0039 (7)	−0.0007 (7)	−0.0088 (7)
C8	0.0192 (8)	0.0170 (7)	0.0184 (8)	−0.0017 (6)	0.0010 (6)	−0.0053 (6)
C9	0.0191 (8)	0.0140 (7)	0.0223 (8)	−0.0018 (6)	0.0023 (6)	−0.0015 (6)
C10	0.0194 (8)	0.0162 (7)	0.0178 (8)	−0.0020 (6)	−0.0001 (6)	0.0018 (6)
C11	0.0187 (8)	0.0229 (8)	0.0196 (8)	−0.0028 (6)	0.0013 (6)	−0.0002 (7)
C12	0.0212 (9)	0.0201 (8)	0.0255 (9)	0.0018 (6)	−0.0015 (7)	0.0036 (7)
C13	0.0199 (8)	0.0207 (8)	0.0164 (8)	0.0011 (6)	−0.0026 (6)	0.0019 (6)
C14	0.0191 (8)	0.0150 (7)	0.0154 (7)	0.0008 (5)	−0.0001 (6)	0.0005 (6)
C15	0.0276 (8)	0.0142 (7)	0.0154 (7)	0.0016 (6)	0.0013 (6)	0.0029 (6)

Geometric parameters (Å, º) top

Cu1—N4	1.9356 (14)	C3—H3	0.9500
Cu1—N2	1.9506 (13)	C4—C5	1.384 (2)
Cu1—N1	2.0204 (13)	C4—H4	0.9500
Cu1—N3	2.0627 (13)	C5—C6	1.490 (2)
Cu1—N5	2.2657 (14)	C6—C7	1.489 (2)
S1—C14	1.6247 (16)	C7—H7A	0.9800
S2—C15	1.6357 (18)	C7—H7B	0.9800
O1—C12	1.425 (2)	C7—H7C	0.9800
O1—C11	1.428 (2)	C8—C9	1.522 (2)
N1—C1	1.336 (2)	C8—H8A	0.9900
N1—C5	1.355 (2)	C8—H8B	0.9900
N2—C6	1.278 (2)	C9—H9A	0.9900
N2—C8	1.460 (2)	C9—H9B	0.9900
N3—C13	1.4904 (19)	C10—C11	1.521 (2)
N3—C10	1.493 (2)	C10—H10A	0.9900
N3—C9	1.4966 (19)	C10—H10B	0.9900
N4—C14	1.164 (2)	C11—H11A	0.9900
N5—C15	1.168 (2)	C11—H11B	0.9900
C1—C2	1.389 (2)	C12—C13	1.518 (2)
C1—H1	0.9500	C12—H12A	0.9900
C2—C3	1.385 (2)	C12—H12B	0.9900
C2—H2	0.9500	C13—H13A	0.9900
C3—C4	1.390 (2)	C13—H13B	0.9900

N4—Cu1—N2	164.55 (6)	C6—C7—H7B	109.5
N4—Cu1—N1	97.15 (5)	H7A—C7—H7B	109.5
N2—Cu1—N1	80.18 (5)	C6—C7—H7C	109.5
N4—Cu1—N3	96.46 (5)	H7A—C7—H7C	109.5
N2—Cu1—N3	83.28 (5)	H7B—C7—H7C	109.5
N1—Cu1—N3	161.32 (5)	N2—C8—C9	107.46 (12)
N4—Cu1—N5	103.06 (5)	N2—C8—H8A	110.2
N2—Cu1—N5	92.35 (5)	C9—C8—H8A	110.2
N1—Cu1—N5	95.29 (5)	N2—C8—H8B	110.2
N3—Cu1—N5	94.03 (5)	C9—C8—H8B	110.2
C12—O1—C11	110.92 (12)	H8A—C8—H8B	108.5
C1—N1—C5	119.27 (14)	N3—C9—C8	110.35 (12)
C1—N1—Cu1	127.79 (11)	N3—C9—H9A	109.6
C5—N1—Cu1	112.82 (10)	C8—C9—H9A	109.6
C6—N2—C8	124.83 (13)	N3—C9—H9B	109.6
C6—N2—Cu1	118.59 (11)	C8—C9—H9B	109.6
C8—N2—Cu1	116.31 (10)	H9A—C9—H9B	108.1
C13—N3—C10	108.51 (12)	N3—C10—C11	112.55 (13)
C13—N3—C9	110.96 (12)	N3—C10—H10A	109.1
C10—N3—C9	112.90 (12)	C11—C10—H10A	109.1
C13—N3—Cu1	112.84 (10)	N3—C10—H10B	109.1
C10—N3—Cu1	107.24 (9)	C11—C10—H10B	109.1
C9—N3—Cu1	104.36 (9)	H10A—C10—H10B	107.8
C14—N4—Cu1	169.48 (13)	O1—C11—C10	110.49 (13)
C15—N5—Cu1	115.52 (12)	O1—C11—H11A	109.6
N1—C1—C2	121.97 (15)	C10—C11—H11A	109.6
N1—C1—H1	119.0	O1—C11—H11B	109.6
C2—C1—H1	119.0	C10—C11—H11B	109.6
C3—C2—C1	118.98 (15)	H11A—C11—H11B	108.1
C3—C2—H2	120.5	O1—C12—C13	110.18 (13)
C1—C2—H2	120.5	O1—C12—H12A	109.6
C2—C3—C4	119.16 (15)	C13—C12—H12A	109.6
C2—C3—H3	120.4	O1—C12—H12B	109.6
C4—C3—H3	120.4	C13—C12—H12B	109.6
C5—C4—C3	118.94 (15)	H12A—C12—H12B	108.1
C5—C4—H4	120.5	N3—C13—C12	112.65 (13)
C3—C4—H4	120.5	N3—C13—H13A	109.1
N1—C5—C4	121.67 (15)	C12—C13—H13A	109.1
N1—C5—C6	114.16 (13)	N3—C13—H13B	109.1
C4—C5—C6	124.17 (14)	C12—C13—H13B	109.1
N2—C6—C7	125.52 (15)	H13A—C13—H13B	107.8
N2—C6—C5	113.64 (14)	N4—C14—S1	178.86 (15)
C7—C6—C5	120.83 (14)	N5—C15—S2	178.35 (15)
C6—C7—H7A	109.5

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···O1ⁱ	0.95	2.40	3.211 (2)	144
C7—H7B···O1ⁱ	0.98	2.33	3.248 (2)	155
C7—H7C···S2ⁱⁱ	0.98	2.83	3.7021 (18)	149
C8—H8B···N5ⁱⁱ	0.99	2.55	3.367 (2)	140
C13—H13A···N4	0.99	2.58	3.181 (2)	119

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

Experimental details

Crystal data
Chemical formula	[Cu(NCS)₂(C₁₃H₁₉N₃O)]
M_r	413.01
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	10.6912 (1), 14.0350 (2), 12.2530 (2)
β (°)	92.203 (1)
V (Å³)	1837.22 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.43
Crystal size (mm)	0.41 × 0.39 × 0.08

Data collection
Diffractometer	Bruker APEXII CCD
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.592, 0.894
No. of measured, independent and observed [I > 2σ(I)] reflections	16491, 4007, 3593
R_int	0.024
(sin θ/λ)_max (Å⁻¹)	0.639

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.023, 0.061, 1.08
No. of reflections	4007
No. of parameters	218
No. of restraints	2
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.37, −0.26

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), X-SEED (Barbour, 2001), SHELXL97 (Sheldrick, 2008) and publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···O1ⁱ	0.95	2.40	3.211 (2)	144
C7—H7B···O1ⁱ	0.98	2.33	3.248 (2)	155
C7—H7C···S2ⁱⁱ	0.98	2.83	3.7021 (18)	149
C8—H8B···N5ⁱⁱ	0.99	2.55	3.367 (2)	140
C13—H13A···N4	0.99	2.58	3.181 (2)	119

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

Acknowledgements

The authors thank the University of Malaya for funding this study (UMRG grant RG024/09BIO).

References

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