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ISSN: 2056-9890

1-Benzoyl-3,3-bis­­(2-methyl­prop­yl)thio­urea

aDepartment of Chemistry, National Institute of Technology, Tiruchirappalli 620 015, India, and bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
*Correspondence e-mail: Edward.Tiekink@gmail.com

(Received 25 January 2011; accepted 7 February 2011; online 12 February 2011)

The title compound, C16H24N2OS, is twisted about the central N(H)—C bond with the C—N—C—S torsion angle being 119.6 (3)°. The carbonyl O and thione S atoms are directed to opposite sides of the mol­ecule, a conformation that allows for the formation of a linear supra­molecular chain comprising alternating eight-membered {⋯HNCS}2 and 14-membered {⋯HCNCNCO}2 synthons.

Related literature

For the coordinating ability of N,N-dialkyl-N′-benzoyl­thio­ureas; see: Binzet et al. (2009[Binzet, G., Kulcu, N., Florke, U. & Arslan, H. (2009). J. Coord. Chem. 62, 3454-3462.]); Gunasekaran et al. (2010[Gunasekaran, N. & Karvembu, R. (2010). Inorg. Chem. Commun. 13, 952-955.]); Sacht et al. (2000[Sacht, C., Datt, M. S., Otto, S. & Roodt, A. (2000). J. Chem. Soc. Dalton Trans. pp. 727-733.]). For the utility of Cd derivatives to serve as synthetic precursors for CdS nanoparticles, see: Bruce et al. (2007[Bruce, J. C., Revaprasadu, N. & Koch, D. R. (2007). New J. Chem. 31, 1647-1653.]). For their biological activity, see: Arslan et al. (2006[Arslan, H., Kulcu, N. & Florke, U. (2006). Spectrochim. Acta Part A, 64, 1065-1071.]). For related structures, see: Gunasekaran et al. (2010a[Gunasekaran, N., Karvembu, R., Ng, S. W. & Tiekink, E. R. T. (2010a). Acta Cryst. E66, o2572-o2573.],b[Gunasekaran, N., Karvembu, R., Ng, S. W. & Tiekink, E. R. T. (2010b). Acta Cryst. E66, o2601.]).

[Scheme 1]

Experimental

Crystal data
  • C16H24N2OS

  • Mr = 292.43

  • Triclinic, [P \overline 1]

  • a = 8.9331 (10) Å

  • b = 10.1023 (9) Å

  • c = 11.0725 (12) Å

  • α = 105.776 (9)°

  • β = 112.734 (10)°

  • γ = 100.782 (9)°

  • V = 837.47 (19) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 0.19 mm−1

  • T = 295 K

  • 0.35 × 0.30 × 0.25 mm

Data collection
  • Agilent Supernova Dual diffractometer with an Atlas detector

  • Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010[Agilent (2010). CrysAlis PRO. Agilent Technologies, Yarnton, Oxfordshire, England.]) Tmin = 0.936, Tmax = 0.954

  • 6265 measured reflections

  • 3693 independent reflections

  • 2232 reflections with I > 2σ(I)

  • Rint = 0.025

Refinement
  • R[F2 > 2σ(F2)] = 0.074

  • wR(F2) = 0.219

  • S = 1.04

  • 3693 reflections

  • 181 parameters

  • 12 restraints

  • H-atom parameters constrained

  • Δρmax = 0.86 e Å−3

  • Δρmin = −0.58 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
N1—H1⋯S1i 0.88 2.74 3.586 (3) 162
C9—H9a⋯O1ii 0.97 2.49 3.424 (5) 162
Symmetry codes: (i) -x+2, -y+2, -z+2; (ii) -x+1, -y+1, -z+1.

Data collection: CrysAlis PRO (Agilent, 2010[Agilent (2010). CrysAlis PRO. Agilent Technologies, Yarnton, Oxfordshire, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; 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 DIAMOND (Brandenburg, 2006[Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany.]); software used to prepare material for publication: publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).

Supporting information


Comment top

N,N-Dialkyl-N'-benzoylthioureas are versatile ligands which can coordinate to transition metal centres either as neutral species or in an anionic form. The complexation capacity of thiourea derivatives has been reported in several studies (Binzet et al., 2009; Gunasekaran et al., 2010). Chiral and achiral platinum(II) complexes of these ligands have been used as chemotherapeutic agents (Sacht et al., 2000) while cadmium(II) complexes of N,N-diethyl-N'-benzoylthiourea have been used as single-source precursors for the preparation of CdS nanoparticles (Bruce et al., 2007). In addition, thioureas have been shown to possess anti-tubercular, anti-helmintic, anti-bacterial, insecticidal and rodenticidal properties (Arslan et al., 2006). In continuation of structural studies of these derivatives (Gunasekaran et al., 2010a; Gunasekaran et al., 2010b), the title compound, (I), was investigated.

In (I), Fig. 1, the molecule exhibits a significant twist about the central N(H)–C bond as seen in the value of the C7–N1–C8–S1 torsion angle of 119.6 (3) °. This arrangement causes the carbonyl-O and thione-S atoms to lie on opposite sides of the molecule. Similarly, the carbonyl and N–H groups are directed away from each other. This conformation allows for the formation of N–H···S hydrogen bonds, Table 1, via an eight-membered {···HNCS}2 ring which has the shape of an elongated chair. These are connected into supramolecular chains along [1 1 1] via C–H···O contacts that close 14-membered {···HCNCNCO}2 synthons, also adopting the shape of an elongated chair, Table 1 and Fig. 2. Chains are arranged into layers via weak π···π interactions [Cg(C1–C6)···Cg(C1–C6)i = 3.806 (3) Å for i: 2 - x, 1 - y, 2 - z] and these stack as shown in Fig. 3.

Related literature top

For the coordinating ability of N,N-dialkyl-N'-benzoylthioureas; see: Binzet et al. (2009); Gunasekaran et al. (2010); Sacht et al. (2000). For the utility of Cd derivatives to serve as synthetic precursors for CdS nanoparticles, see: Bruce et al. (2007). For their biological activity, see: Arslan et al. (2006). For related structures, see: Gunasekaran et al. (2010a,b).

Experimental top

A solution of benzoyl chloride (0.7029 g, 5 mmol) in acetone (50 ml) was added drop wise to a suspension of potassium thiocyanate (0.4859 g, 5 mmol) in anhydrous acetone (50 ml). The reaction mixture was heated under reflux for 45 min. and then cooled to room temperature. A solution of diisobutyl amine (0.6462 g, 5 mmol) in acetone (30 ml) was added and the resulting mixture was stirred for 2 h. Hydrochloric acid (0.1 N, 300 ml) was added and the resulting white solid was filtered, washed with water and dried in vacuo. Single crystals for X-ray diffraction were grown at room temperature from an acetonitrile solution of the compound. Yield 72%; M.Pt. 415 K. FT—IR (KBr) ν(N—H) 3268, ν(CO) 1688, ν(C=S) 1264 cm-1.

Refinement top

The H-atoms were placed in calculated positions (N—H = 0.88; C—H 0.93 to 0.98 Å) and were included in the refinement in the riding model approximation, with Uiso(H) set to 1.2 to 1.5Uequiv(N, C).

Computing details top

Data collection: CrysAlis PRO (Agilent, 2010); cell refinement: CrysAlis PRO (Agilent, 2010); data reduction: CrysAlis PRO (Agilent, 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 DIAMOND (Brandenburg, 2006); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top
[Figure 1] Fig. 1. The molecular structure of (I) showing the atom-labelling scheme and displacement ellipsoids at the 35% probability level.
[Figure 2] Fig. 2. Supramolecular chain in (I) mediated by N–H···S hydrogen bonds and C–H···O contacts, shown as orange and blue dashed lines, respectively.
[Figure 3] Fig. 3. View in projection down the b axis of the unit cell contents of (I). The N–H···S hydrogen bonds and C–H···O contacts are shown as orange and blue dashed lines, respectively.
1-Benzoyl-3,3-bis(2-methylpropyl)thiourea top
Crystal data top
C16H24N2OSZ = 2
Mr = 292.43F(000) = 316
Triclinic, P1Dx = 1.160 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 8.9331 (10) ÅCell parameters from 1845 reflections
b = 10.1023 (9) Åθ = 2.2–29.2°
c = 11.0725 (12) ŵ = 0.19 mm1
α = 105.776 (9)°T = 295 K
β = 112.734 (10)°Block, colourless
γ = 100.782 (9)°0.35 × 0.30 × 0.25 mm
V = 837.47 (19) Å3
Data collection top
Agilent Supernova Dual
diffractometer with an Atlas detector
3693 independent reflections
Radiation source: SuperNova (Mo) X-ray Source2232 reflections with I > 2σ(I)
Mirror monochromatorRint = 0.025
Detector resolution: 10.4041 pixels mm-1θmax = 27.5°, θmin = 2.2°
ω scansh = 1011
Absorption correction: multi-scan
(CrysAlis PRO; Agilent, 2010)
k = 1312
Tmin = 0.936, Tmax = 0.954l = 1412
6265 measured reflections
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)] = 0.074Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.219H-atom parameters constrained
S = 1.04 w = 1/[σ2(Fo2) + (0.078P)2 + 0.7593P]
where P = (Fo2 + 2Fc2)/3
3693 reflections(Δ/σ)max = 0.001
181 parametersΔρmax = 0.86 e Å3
12 restraintsΔρmin = 0.58 e Å3
Crystal data top
C16H24N2OSγ = 100.782 (9)°
Mr = 292.43V = 837.47 (19) Å3
Triclinic, P1Z = 2
a = 8.9331 (10) ÅMo Kα radiation
b = 10.1023 (9) ŵ = 0.19 mm1
c = 11.0725 (12) ÅT = 295 K
α = 105.776 (9)°0.35 × 0.30 × 0.25 mm
β = 112.734 (10)°
Data collection top
Agilent Supernova Dual
diffractometer with an Atlas detector
3693 independent reflections
Absorption correction: multi-scan
(CrysAlis PRO; Agilent, 2010)
2232 reflections with I > 2σ(I)
Tmin = 0.936, Tmax = 0.954Rint = 0.025
6265 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.07412 restraints
wR(F2) = 0.219H-atom parameters constrained
S = 1.04Δρmax = 0.86 e Å3
3693 reflectionsΔρmin = 0.58 e Å3
181 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 > 2σ(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
xyzUiso*/Ueq
S10.74828 (14)0.92803 (11)0.99096 (12)0.0711 (4)
O10.6998 (3)0.5295 (2)0.7153 (3)0.0585 (7)
N10.8690 (3)0.7638 (3)0.8494 (3)0.0512 (7)
H10.97530.82360.89090.061*
N20.6172 (3)0.7981 (3)0.7098 (3)0.0515 (7)
C10.9961 (4)0.5699 (3)0.8524 (3)0.0431 (7)
C20.9697 (5)0.4222 (4)0.8112 (4)0.0535 (9)
H20.85970.35660.74870.064*
C31.1045 (5)0.3706 (4)0.8615 (5)0.0653 (11)
H31.08470.27080.83350.078*
C41.2664 (5)0.4656 (5)0.9522 (5)0.0669 (11)
H41.35680.43060.98660.080*
C51.2961 (5)0.6133 (5)0.9929 (5)0.0661 (11)
H51.40690.67801.05420.079*
C61.1618 (4)0.6657 (4)0.9431 (4)0.0538 (9)
H61.18260.76560.97050.065*
C70.8421 (4)0.6165 (3)0.7986 (3)0.0426 (7)
C80.7372 (4)0.8250 (3)0.8392 (4)0.0513 (9)
C90.6351 (4)0.7432 (3)0.5811 (4)0.0526 (9)
H9A0.53520.65880.51220.063*
H9B0.73530.71180.60350.063*
C100.6535 (5)0.8564 (4)0.5150 (4)0.0654 (11)
H100.54630.87920.48310.079*
C110.6790 (7)0.7906 (5)0.3856 (4)0.0892 (15)
H11A0.58490.70250.32040.134*
H11B0.78470.76910.41490.134*
H11C0.68350.85870.34030.134*
C120.7998 (6)0.9970 (4)0.6237 (5)0.0877 (15)
H12A0.80911.06610.58010.132*
H12B0.90570.97650.65830.132*
H12C0.77651.03670.70120.132*
C130.4659 (4)0.8426 (4)0.6909 (5)0.0662 (11)
H13A0.42060.85360.60050.079*
H13B0.50250.93770.76400.079*
C140.3240 (5)0.7441 (4)0.6949 (7)0.106 (2)
H140.36400.76250.79570.127*
C150.1645 (5)0.7914 (5)0.6518 (6)0.0888 (15)
H15A0.19790.89500.69870.133*
H15B0.08630.74350.67850.133*
H15C0.10940.76550.55120.133*
C160.2816 (6)0.5830 (4)0.6261 (6)0.0816 (13)
H16A0.38530.55860.65540.122*
H16B0.22640.55420.52510.122*
H16C0.20580.53300.65360.122*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0676 (7)0.0507 (6)0.0765 (7)0.0191 (5)0.0294 (6)0.0036 (5)
O10.0434 (13)0.0383 (13)0.0653 (16)0.0071 (11)0.0031 (12)0.0157 (12)
N10.0344 (14)0.0355 (15)0.0622 (18)0.0091 (12)0.0100 (13)0.0078 (13)
N20.0364 (14)0.0400 (15)0.0659 (19)0.0137 (12)0.0144 (14)0.0156 (14)
C10.0428 (17)0.0444 (18)0.0423 (17)0.0167 (15)0.0181 (14)0.0176 (14)
C20.054 (2)0.0427 (19)0.059 (2)0.0190 (16)0.0215 (17)0.0169 (17)
C30.069 (3)0.054 (2)0.088 (3)0.034 (2)0.040 (2)0.034 (2)
C40.055 (2)0.077 (3)0.089 (3)0.039 (2)0.035 (2)0.046 (3)
C50.0419 (19)0.071 (3)0.077 (3)0.0192 (19)0.0186 (18)0.029 (2)
C60.0451 (19)0.050 (2)0.060 (2)0.0171 (16)0.0180 (16)0.0193 (17)
C70.0417 (17)0.0384 (17)0.0383 (16)0.0125 (14)0.0111 (14)0.0128 (14)
C80.0403 (17)0.0325 (17)0.067 (2)0.0098 (14)0.0173 (16)0.0118 (16)
C90.0438 (18)0.0412 (19)0.060 (2)0.0136 (15)0.0125 (16)0.0183 (17)
C100.055 (2)0.052 (2)0.075 (3)0.0160 (18)0.0104 (19)0.032 (2)
C110.113 (4)0.077 (3)0.071 (3)0.025 (3)0.033 (3)0.038 (3)
C120.092 (3)0.052 (3)0.089 (3)0.000 (2)0.021 (3)0.030 (2)
C130.046 (2)0.057 (2)0.089 (3)0.0247 (18)0.022 (2)0.027 (2)
C140.065 (3)0.072 (3)0.203 (7)0.033 (3)0.070 (4)0.065 (4)
C150.060 (3)0.097 (4)0.139 (5)0.039 (3)0.057 (3)0.060 (4)
C160.071 (3)0.057 (3)0.113 (4)0.012 (2)0.047 (3)0.027 (3)
Geometric parameters (Å, º) top
S1—C81.673 (4)C9—H9B0.9700
O1—C71.214 (4)C10—C121.528 (4)
N1—C71.377 (4)C10—C111.529 (4)
N1—C81.410 (4)C10—H100.9800
N1—H10.8800C11—H11A0.9600
N2—C81.330 (4)C11—H11B0.9600
N2—C131.461 (4)C11—H11C0.9600
N2—C91.464 (5)C12—H12A0.9600
C1—C21.380 (5)C12—H12B0.9600
C1—C61.386 (5)C12—H12C0.9600
C1—C71.493 (4)C13—C141.482 (4)
C2—C31.381 (5)C13—H13A0.9700
C2—H20.9300C13—H13B0.9700
C3—C41.362 (6)C14—C161.498 (4)
C3—H30.9300C14—C151.530 (4)
C4—C51.376 (6)C14—H140.9800
C4—H40.9300C15—H15A0.9600
C5—C61.382 (5)C15—H15B0.9600
C5—H50.9300C15—H15C0.9600
C6—H60.9300C16—H16A0.9600
C9—C101.533 (4)C16—H16B0.9600
C9—H9A0.9700C16—H16C0.9600
C7—N1—C8124.2 (3)C12—C10—H10108.2
C7—N1—H1117.9C11—C10—H10108.2
C8—N1—H1117.9C9—C10—H10108.2
C8—N2—C13120.0 (3)C10—C11—H11A109.5
C8—N2—C9124.2 (3)C10—C11—H11B109.5
C13—N2—C9115.2 (3)H11A—C11—H11B109.5
C2—C1—C6118.6 (3)C10—C11—H11C109.5
C2—C1—C7117.4 (3)H11A—C11—H11C109.5
C6—C1—C7124.0 (3)H11B—C11—H11C109.5
C1—C2—C3120.9 (4)C10—C12—H12A109.5
C1—C2—H2119.6C10—C12—H12B109.5
C3—C2—H2119.6H12A—C12—H12B109.5
C4—C3—C2120.1 (4)C10—C12—H12C109.5
C4—C3—H3119.9H12A—C12—H12C109.5
C2—C3—H3119.9H12B—C12—H12C109.5
C3—C4—C5120.0 (3)N2—C13—C14116.6 (3)
C3—C4—H4120.0N2—C13—H13A108.1
C5—C4—H4120.0C14—C13—H13A108.1
C4—C5—C6120.2 (4)N2—C13—H13B108.1
C4—C5—H5119.9C14—C13—H13B108.1
C6—C5—H5119.9H13A—C13—H13B107.3
C5—C6—C1120.2 (3)C13—C14—C16118.4 (4)
C5—C6—H6119.9C13—C14—C15111.0 (3)
C1—C6—H6119.9C16—C14—C15112.5 (4)
O1—C7—N1121.4 (3)C13—C14—H14104.5
O1—C7—C1122.1 (3)C16—C14—H14104.5
N1—C7—C1116.6 (3)C15—C14—H14104.5
N2—C8—N1117.1 (3)C14—C15—H15A109.5
N2—C8—S1125.9 (3)C14—C15—H15B109.5
N1—C8—S1117.1 (3)H15A—C15—H15B109.5
N2—C9—C10113.3 (3)C14—C15—H15C109.5
N2—C9—H9A108.9H15A—C15—H15C109.5
C10—C9—H9A108.9H15B—C15—H15C109.5
N2—C9—H9B108.9C14—C16—H16A109.5
C10—C9—H9B108.9C14—C16—H16B109.5
H9A—C9—H9B107.7H16A—C16—H16B109.5
C12—C10—C11112.2 (3)C14—C16—H16C109.5
C12—C10—C9110.9 (3)H16A—C16—H16C109.5
C11—C10—C9109.1 (3)H16B—C16—H16C109.5
C6—C1—C2—C31.4 (5)C13—N2—C8—N1172.5 (3)
C7—C1—C2—C3177.1 (3)C9—N2—C8—N116.3 (5)
C1—C2—C3—C40.5 (6)C13—N2—C8—S19.0 (5)
C2—C3—C4—C50.5 (6)C9—N2—C8—S1162.2 (3)
C3—C4—C5—C60.6 (7)C7—N1—C8—N261.8 (5)
C4—C5—C6—C10.4 (6)C7—N1—C8—S1119.6 (3)
C2—C1—C6—C51.4 (5)C8—N2—C9—C10109.9 (4)
C7—C1—C6—C5177.1 (3)C13—N2—C9—C1061.7 (4)
C8—N1—C7—O115.7 (5)N2—C9—C10—C1253.6 (4)
C8—N1—C7—C1163.6 (3)N2—C9—C10—C11177.6 (3)
C2—C1—C7—O14.2 (5)C8—N2—C13—C1482.1 (5)
C6—C1—C7—O1177.4 (3)C9—N2—C13—C14105.9 (4)
C2—C1—C7—N1175.2 (3)N2—C13—C14—C1639.2 (7)
C6—C1—C7—N13.3 (5)N2—C13—C14—C15171.4 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···S1i0.882.743.586 (3)162
C9—H9a···O1ii0.972.493.424 (5)162
Symmetry codes: (i) x+2, y+2, z+2; (ii) x+1, y+1, z+1.

Experimental details

Crystal data
Chemical formulaC16H24N2OS
Mr292.43
Crystal system, space groupTriclinic, P1
Temperature (K)295
a, b, c (Å)8.9331 (10), 10.1023 (9), 11.0725 (12)
α, β, γ (°)105.776 (9), 112.734 (10), 100.782 (9)
V3)837.47 (19)
Z2
Radiation typeMo Kα
µ (mm1)0.19
Crystal size (mm)0.35 × 0.30 × 0.25
Data collection
DiffractometerAgilent Supernova Dual
diffractometer with an Atlas detector
Absorption correctionMulti-scan
(CrysAlis PRO; Agilent, 2010)
Tmin, Tmax0.936, 0.954
No. of measured, independent and
observed [I > 2σ(I)] reflections
6265, 3693, 2232
Rint0.025
(sin θ/λ)max1)0.650
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.074, 0.219, 1.04
No. of reflections3693
No. of parameters181
No. of restraints12
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.86, 0.58

Computer programs: CrysAlis PRO (Agilent, 2010), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2006), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···S1i0.882.743.586 (3)162
C9—H9a···O1ii0.972.493.424 (5)162
Symmetry codes: (i) x+2, y+2, z+2; (ii) x+1, y+1, z+1.
 

Footnotes

Additional correspondence author, e-mail: kar@nitt.edu.

Acknowledgements

NS thanks the NITT for a Fellowship. The authors thank the University of Malaya for supporting this study.

References

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