metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 68| Part 5| May 2012| Pages m538-m539

Bis[2-(2-oxoindolin-3-yl­­idene)-N-phenylhydrazinecarbo­thio­amidato-κ3O,N2,S]nickel(II) di­methyl­formamide monosolvate

aSchool of Chemical Sciences, Universiti Sains Malaysia, Minden, Penang, Malaysia, bFaculty of Science, Sabha University, Libya, cDepartment of Chemistry, International University of Africa, Khartoum, Sudan, and dX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia
*Correspondence e-mail: sgteoh@usm.my

(Received 20 February 2012; accepted 23 March 2012; online 4 April 2012)

The asymmetric unit of the title compound, [Ni(C15H11N4OS)2]·C3H7NO, contains one NiII complex mol­ecule and one disordered dimethyl­formamide solvent mol­ecule. The NiII ion is six-coordinated in a distorted octa­hedral geometry by two N, two O and two S atoms. An intra­molecular C—H⋯S hydrogen bond generates an S(6) ring motif. In the crystal, mol­ecules are linked through inter­molecular N—H⋯S, N—H⋯O, C—H⋯N, C—H⋯O and C—H⋯S hydrogen bonds into infinite two-dimensional network parallel to the ab plane. The structure is further stablized by weak C—H⋯π inter­actions. The dimethylformamide solvent molecule is disordered over two sets of sites in a 0.514 (15):0.486 (15) ratio.

Related literature

For related structures, see: Qasem Ali et al. (2011a[Qasem Ali, A., Eltayeb, N. E., Teoh, S. G., Salhin, A. & Fun, H.-K. (2011a). Acta Cryst. E67, o3141-o3142.],b[Qasem Ali, A., Eltayeb, N. E., Teoh, S. G., Salhin, A. & Fun, H.-K. (2011b). Acta Cryst. E67, o3476-o3477.], 2012a[Qasem Ali, A., Eltayeb, N. E., Teoh, S. G., Salhin, A. & Fun, H.-K. (2012a). Acta Cryst. E68, o953-o954.],b[Qasem Ali, A., Eltayeb, N. E., Teoh, S. G., Salhin, A. & Fun, H.-K. (2012b). Acta Cryst. E68, o962-o963.]); Ali et al. (2012[Ali, A. Q., Eltayeb, N. E., Teoh, S. G., Salhin, A. & Fun, H.-K. (2012). Acta Cryst. E68, o285-o286.]). For the biological activity of Schiff bases, see: Bhandari et al. (2008[Bhandari, S. V., Bothara, K. G., Raut, M. K., Patil, A. A., Sarkate, A. P. & Mokale, V. J. (2008). Bioorg. Med. Chem. 16, 1822-1831.]); Bhardwaj et al. (2010[Bhardwaj, S., Kumar, L., Verma, R. & Sing, U. K. (2010). J. Pharm. Res. 3, 2983-2985.]); Pandeya et al. (1999[Pandeya, S. N., Sriram, D., Nath, G. & Clercq, E. De. (1999). Indian J. Pharm. Sci. 61, 358-361.]); Sridhar et al. (2002[Sridhar, S. K., Pandeya, S. N., Stables, J. P. & Ramesh, A. (2002). Eur. J. Pharm. Sci. 16, 129-132.]); Suryavanshi & Pai (2006[Suryavanshi, J. P. & Pai, N. R. (2006). Indian J. Chem. Sect. B, 45, 1227-1230.]). For the cytotoxic and anti­cancer activity of isatin and its derivatives, see: Vine et al. (2009[Vine, K. L., Matesic, L., Locke, J. M., Ranson, M. & Skropeta, D. (2009). Anti-Cancer Agents Med. Chem. 9, 397-414.]). For graph-set analysis, see: Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]). For bond-length data, see: Allen et al. (1987[Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.]).

[Scheme 1]

Experimental

Crystal data
  • [Ni(C15H11N4OS)2]·C3H7NO

  • Mr = 722.48

  • Triclinic, [P \overline 1]

  • a = 12.2491 (2) Å

  • b = 12.3170 (3) Å

  • c = 13.1142 (2) Å

  • α = 104.854 (1)°

  • β = 112.943 (1)°

  • γ = 102.798 (1)°

  • V = 1642.31 (5) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 0.77 mm−1

  • T = 100 K

  • 0.45 × 0.15 × 0.13 mm

Data collection
  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2005[Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.723, Tmax = 0.906

  • 34412 measured reflections

  • 9435 independent reflections

  • 7397 reflections with I > 2σ(I)

  • Rint = 0.033

Refinement
  • R[F2 > 2σ(F2)] = 0.041

  • wR(F2) = 0.107

  • S = 1.03

  • 9435 reflections

  • 481 parameters

  • 25 restraints

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.63 e Å−3

  • Δρmin = −0.37 e Å−3

Table 1
Selected bond lengths (Å)

Ni1—N2 2.0342 (15)
Ni1—N6 2.0373 (15)
Ni1—O1 2.1886 (13)
Ni1—O2 2.2441 (13)
Ni1—S1 2.3564 (5)
Ni1—S2 2.3866 (5)

Table 2
Hydrogen-bond geometry (Å, °)

Cg5, Cg7, Cg9 and Cg10 are the centroids of the N1/C1/C8/C7/C2, C2–C7, C17–C22 and C25–C30 rings, respectively.

D—H⋯A D—H H⋯A DA D—H⋯A
N8—H1N8⋯S2i 0.86 (2) 2.48 (3) 3.301 (2) 159 (2)
N1—H1N1⋯O1ii 0.79 (4) 2.04 (4) 2.811 (2) 165 (4)
N5—H1N5⋯O3Xiii 0.89 (4) 1.84 (4) 2.729 (9) 173 (3)
N4—H1N4⋯O2iv 0.82 (3) 2.22 (3) 3.006 (3) 161 (2)
C3—H3A⋯N7ii 0.95 2.56 3.500 (3) 173
C11—H11A⋯O2iv 0.95 2.55 3.349 (3) 142
C15—H15A⋯S1 0.95 2.53 3.194 (3) 127
C20—H20A⋯S1v 0.95 2.71 3.443 (2) 135
C30—H30A⋯S2i 0.95 2.84 3.551 (2) 132
C31X—H31ECg9vi 0.98 2.97 3.567 (11) 121
C31X—H31FCg7iv 0.98 2.79 3.460 (10) 126
C32X—H32DCg10vii 0.98 2.91 3.769 (12) 147
C31—H31BCg9vi 0.98 2.98 3.66 (2) 128
C31—H31CCg7iv 0.98 2.78 3.47 (2) 127
C32—H32BCg5iv 0.98 2.82 3.577 (16) 135
Symmetry codes: (i) -x+1, -y, -z+1; (ii) -x+2, -y, -z+1; (iii) -x+2, -y+1, -z; (iv) -x+2, -y+1, -z+1; (v) -x+1, -y, -z; (vi) x, y+1, z; (vii) x+1, y+1, z.

Data collection: APEX2 (Bruker, 2005[Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2005[Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; 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: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).

Supporting information


Comment top

Isatin (2,3-dioxindole) is an endogenous compound identified in humans, and its effect has been studied in a variety of systems. Biological properties of isatin and its derivatives include a range of actions in the brain, offer protection against bacterial (Suryavanshi & Pai, 2006) and fungal infections and possess anticonvulsant, anti-HIV (Pandeya et al., 1999), anti-depressant and anti-inflammatory activities (Bhandari et al., 2008). Recently, we reported the crystal structure of (Z)-N-methyl-2-(5-nitro-2-oxoindolin-3-ylidene) hydrazinecarbothioamide (Qasem Ali et al., 2012a). In the present paper we describe the single-crystal X-ray diffraction study of title compound, Fig.1.

In the title compound, (Fig. 1), the asymmetric unit contains one NiII complex, [Ni(C15H11N4OS)2] and one solvent molecule, [C3H7NO], which displays disorder. NiII ion is six-coordinated in a distorted octahedral geometry by two N, two O and two S atoms. The Ni—N, Ni—O and Ni—S bond distances (Table 1) and the bond angles around Ni1 are normal (Allen et al., 1987).

Intramolecular C15—H15A···S1 hydrogen bond generate an S(6) rings motif (Bernstein et al., 1995)] (Table 2). Intramolecular interactions C26—H26A···N7 and C32X—H32D···O3X are also present.

In the crystal, molecules are linked through intermolecular N8—H1N8···S2, N1—H1N1···O1, N5—H1N5···O3X, N4—H1N4···O2, C3—H3A···N7, C11—H11A···O2, C20—H20A···S1 and C30—H30A···S2 hydrogen bonds into infinite two-dimensional network, (Table 1, Fig.2). Weak C—H···π interactions are also present: C31X—H31E···Cg9, C31X—H31F···Cg7, C32X—H32D···Cg10, C31—H31B···Cg9, C31—H31C···Cg7 and C32—H32B···Cg5 (Table 2). Cg5, Cg7, Cg9 and Cg10 are centroid of N1/C1/C8/C7/C2, C2—C7, C17—C22 and C25—C30 ring, respectively.

Related literature top

For related structures, see: Qasem Ali et al. (2012a,b, 2011a,b); Ali et al. (2012). For the biological activity of Schiff bases, see: Bhandari et al. (2008); Bhardwaj et al. (2010); Pandeya et al. (1999); Sridhar et al. (2002); Suryavanshi & Pai (2006). For the cytotoxic and anticancer activity of isatin and its derivatives, see: Vine et al. (2009). For graph-set analysis, see Bernstein et al. (1995). For bond-length data, see: Allen et al. (1987).

Experimental top

The Ni-complex has been synthesized by refluxing the reaction mixture of hot ethanolic solution (30 ml) of NiCl2 (0.01 mol) and hot ethanolic solution (30 ml) of the ligand as reported before (Qasem Ali, 2012b) (0.02 mol) for 2 hrs. The precipitate formed during reflux was filtered, washed with cold EtOH and recrystallized from hot EtOH. Yield (m.p.): 67% (>573 K). The green crystals were grown in acetone-DMF (4:1) by slow evaporation at room temperature.

Refinement top

N bound atoms were located in a difference Fourier map and were refined freely. The H atoms were positioned geometrically and refined using a riding model with C–H = 0.95 Å for aromatic ring and and C–H = 0.96–0.98 Å for methyl group with Uiso(H) = 1.2Ueq(C) and Uiso(H) = 1.5Ueq(C) for aromatic ring and methyl group respectively. The highest residual electron density peak is located at 0.97 Å from H33B and the deepest hole is located at 0.58 Å from N9.

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXS97(Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound, with 50% probability displacement ellipsoids and the atom-numbering scheme.
[Figure 2] Fig. 2. The crystal packing of the title compound viewed down the a axis. Hydrogen bonds are shown as dashed lines.
Bis[2-(2-oxoindolin-3-ylidene)-N-phenylhydrazinecarbothioamidato- κ3O,N2,S]nickel(II) dimethylformamide monosolvate top
Crystal data top
[Ni(C15H11N4OS)2]·C3H7NOZ = 2
Mr = 722.48F(000) = 748
Triclinic, P1Dx = 1.461 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 12.2491 (2) ÅCell parameters from 9906 reflections
b = 12.3170 (3) Åθ = 2.7–29.9°
c = 13.1142 (2) ŵ = 0.77 mm1
α = 104.854 (1)°T = 100 K
β = 112.943 (1)°Needle, green
γ = 102.798 (1)°0.45 × 0.15 × 0.13 mm
V = 1642.31 (5) Å3
Data collection top
Bruker APEXII CCD
diffractometer
9435 independent reflections
Radiation source: fine-focus sealed tube7397 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.033
ϕ and ω scansθmax = 30.0°, θmin = 1.8°
Absorption correction: multi-scan
(SADABS; Bruker, 2005)
h = 1616
Tmin = 0.723, Tmax = 0.906k = 1617
34412 measured reflectionsl = 1818
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)] = 0.041Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.107H atoms treated by a mixture of independent and constrained refinement
S = 1.03 w = 1/[σ2(Fo2) + (0.0498P)2 + 0.8476P]
where P = (Fo2 + 2Fc2)/3
9435 reflections(Δ/σ)max = 0.002
481 parametersΔρmax = 0.63 e Å3
25 restraintsΔρmin = 0.37 e Å3
Crystal data top
[Ni(C15H11N4OS)2]·C3H7NOγ = 102.798 (1)°
Mr = 722.48V = 1642.31 (5) Å3
Triclinic, P1Z = 2
a = 12.2491 (2) ÅMo Kα radiation
b = 12.3170 (3) ŵ = 0.77 mm1
c = 13.1142 (2) ÅT = 100 K
α = 104.854 (1)°0.45 × 0.15 × 0.13 mm
β = 112.943 (1)°
Data collection top
Bruker APEXII CCD
diffractometer
9435 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2005)
7397 reflections with I > 2σ(I)
Tmin = 0.723, Tmax = 0.906Rint = 0.033
34412 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.04125 restraints
wR(F2) = 0.107H atoms treated by a mixture of independent and constrained refinement
S = 1.03Δρmax = 0.63 e Å3
9435 reflectionsΔρmin = 0.37 e Å3
481 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
xyzUiso*/UeqOcc. (<1)
Ni10.78451 (2)0.19687 (2)0.41425 (2)0.01968 (7)
S10.70744 (4)0.35633 (4)0.42739 (5)0.02561 (11)
S20.65024 (5)0.08658 (4)0.47337 (4)0.02594 (11)
O10.90909 (12)0.09464 (11)0.45887 (12)0.0248 (3)
O20.87054 (12)0.23656 (11)0.29881 (12)0.0241 (3)
N11.12110 (15)0.15001 (14)0.60044 (15)0.0242 (3)
N20.94274 (14)0.33207 (13)0.55479 (14)0.0201 (3)
N30.95747 (15)0.44742 (13)0.59700 (14)0.0223 (3)
N40.86366 (17)0.58352 (14)0.58507 (16)0.0260 (4)
N50.83284 (18)0.11914 (17)0.10848 (16)0.0309 (4)
N60.66127 (14)0.05595 (13)0.25591 (14)0.0199 (3)
N70.55864 (15)0.03271 (14)0.23367 (14)0.0223 (3)
N80.44456 (16)0.10476 (15)0.32126 (16)0.0271 (4)
C11.01396 (18)0.17003 (16)0.54342 (17)0.0220 (4)
C21.22052 (18)0.26024 (16)0.68514 (17)0.0228 (4)
C31.34585 (19)0.27929 (18)0.75792 (18)0.0272 (4)
H3A1.37610.21450.75650.033*
C41.42602 (19)0.39775 (18)0.83346 (19)0.0302 (4)
H4A1.51280.41400.88490.036*
C51.38212 (19)0.49286 (18)0.83545 (18)0.0286 (4)
H5A1.43920.57260.88830.034*
C61.25508 (18)0.47278 (17)0.76076 (17)0.0247 (4)
H6A1.22540.53780.76140.030*
C71.17367 (18)0.35500 (16)0.68558 (16)0.0220 (4)
C81.04087 (17)0.29907 (15)0.59716 (16)0.0205 (3)
C90.84681 (17)0.46578 (16)0.54011 (17)0.0217 (4)
C100.78016 (19)0.64753 (17)0.56415 (18)0.0248 (4)
C110.8371 (2)0.77289 (18)0.6156 (2)0.0306 (4)
H11A0.92710.80960.65970.037*
C120.7638 (2)0.8445 (2)0.6031 (2)0.0362 (5)
H12A0.80390.92970.63830.043*
C130.6330 (2)0.7927 (2)0.5401 (2)0.0353 (5)
H13A0.58260.84160.53180.042*
C140.5770 (2)0.6699 (2)0.4895 (3)0.0444 (6)
H14A0.48690.63400.44590.053*
C150.6487 (2)0.5963 (2)0.5005 (2)0.0418 (6)
H15A0.60760.51120.46450.050*
C160.80929 (18)0.14680 (17)0.20257 (17)0.0246 (4)
C170.7387 (2)0.00967 (19)0.01605 (18)0.0292 (4)
C180.7279 (2)0.0482 (2)0.0946 (2)0.0383 (5)
H18A0.78920.01720.11710.046*
C190.6232 (2)0.1538 (2)0.1715 (2)0.0385 (5)
H19A0.61210.19510.24880.046*
C200.5349 (2)0.2000 (2)0.13809 (19)0.0347 (5)
H20A0.46470.27250.19270.042*
C210.5470 (2)0.14246 (18)0.02595 (18)0.0289 (4)
H21A0.48640.17500.00320.035*
C220.64997 (19)0.03614 (17)0.05159 (17)0.0248 (4)
C230.69379 (17)0.04848 (16)0.17166 (16)0.0217 (4)
C240.54556 (18)0.02168 (16)0.33181 (17)0.0236 (4)
C250.35014 (19)0.21055 (18)0.22267 (18)0.0282 (4)
C260.3149 (2)0.2297 (2)0.10356 (19)0.0317 (4)
H26A0.35590.16990.08350.038*
C270.2200 (2)0.3359 (2)0.0138 (2)0.0381 (5)
H27A0.19630.34840.06760.046*
C280.1592 (2)0.4240 (2)0.0413 (2)0.0438 (6)
H28A0.09500.49710.02070.053*
C290.1926 (2)0.4047 (2)0.1598 (2)0.0456 (6)
H29A0.15000.46440.17900.055*
C300.2880 (2)0.2989 (2)0.2512 (2)0.0361 (5)
H30A0.31090.28650.33250.043*
N90.8695 (2)0.7307 (2)0.0180 (3)0.0608 (7)
C330.8769 (3)0.7217 (4)0.0834 (4)0.0751 (11)
H33A0.81430.66830.16240.090*0.486 (15)
H33B0.79320.69480.14950.090*0.514 (15)
O30.9859 (7)0.7999 (10)0.0528 (10)0.070 (2)0.486 (15)
C310.7511 (15)0.6693 (17)0.0101 (17)0.113 (6)0.486 (15)
H31A0.69010.61780.07360.169*0.486 (15)
H31B0.71790.72840.04040.169*0.486 (15)
H31C0.76400.61970.05830.169*0.486 (15)
C320.9682 (15)0.8108 (15)0.1582 (11)0.140 (7)0.486 (15)
H32A1.05400.84230.16810.210*0.486 (15)
H32B0.96710.76060.20520.210*0.486 (15)
H32C0.94300.87810.18610.210*0.486 (15)
O3X0.9563 (5)0.7356 (8)0.1188 (8)0.056 (2)0.514 (15)
C31X0.7529 (9)0.6800 (9)0.0153 (8)0.040 (2)0.514 (15)
H31D0.68580.63750.06800.061*0.514 (15)
H31E0.73190.74410.05640.061*0.514 (15)
H31F0.76000.62320.05580.061*0.514 (15)
C32X0.9868 (9)0.7923 (8)0.1185 (9)0.070 (3)0.514 (15)
H32D1.05350.78150.09790.105*0.514 (15)
H32E0.99020.76090.18080.105*0.514 (15)
H32F1.00010.87820.14830.105*0.514 (15)
H1N80.442 (2)0.092 (2)0.388 (2)0.037 (7)*
H1N11.127 (3)0.086 (3)0.590 (2)0.045 (8)*
H1N50.901 (3)0.162 (3)0.107 (3)0.055 (8)*
H1N40.938 (2)0.627 (2)0.630 (2)0.033 (7)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ni10.01728 (12)0.01467 (11)0.02259 (12)0.00379 (9)0.00726 (9)0.00553 (9)
S10.0183 (2)0.0182 (2)0.0310 (2)0.00567 (18)0.00575 (19)0.00578 (19)
S20.0247 (2)0.0222 (2)0.0242 (2)0.00144 (19)0.0111 (2)0.00564 (18)
O10.0202 (7)0.0157 (6)0.0281 (7)0.0044 (5)0.0050 (6)0.0051 (5)
O20.0210 (7)0.0196 (6)0.0250 (7)0.0007 (5)0.0099 (6)0.0057 (5)
N10.0217 (8)0.0147 (7)0.0282 (8)0.0075 (6)0.0055 (7)0.0054 (6)
N20.0200 (8)0.0149 (7)0.0234 (7)0.0055 (6)0.0090 (6)0.0069 (6)
N30.0204 (8)0.0141 (7)0.0272 (8)0.0057 (6)0.0081 (6)0.0056 (6)
N40.0191 (8)0.0163 (7)0.0359 (9)0.0069 (7)0.0087 (7)0.0065 (7)
N50.0284 (9)0.0325 (9)0.0300 (9)0.0049 (8)0.0165 (8)0.0103 (8)
N60.0156 (7)0.0163 (7)0.0244 (8)0.0043 (6)0.0075 (6)0.0073 (6)
N70.0182 (8)0.0192 (7)0.0256 (8)0.0038 (6)0.0094 (6)0.0071 (6)
N80.0243 (9)0.0248 (8)0.0254 (8)0.0006 (7)0.0117 (7)0.0065 (7)
C10.0213 (9)0.0161 (8)0.0246 (9)0.0070 (7)0.0078 (7)0.0064 (7)
C20.0216 (9)0.0174 (8)0.0240 (9)0.0062 (7)0.0074 (7)0.0060 (7)
C30.0243 (10)0.0220 (9)0.0305 (10)0.0101 (8)0.0081 (8)0.0092 (8)
C40.0219 (10)0.0269 (10)0.0308 (10)0.0064 (8)0.0043 (8)0.0095 (8)
C50.0238 (10)0.0200 (9)0.0281 (10)0.0027 (8)0.0045 (8)0.0054 (8)
C60.0251 (10)0.0182 (8)0.0262 (9)0.0067 (8)0.0096 (8)0.0066 (7)
C70.0209 (9)0.0187 (8)0.0228 (9)0.0067 (7)0.0075 (7)0.0076 (7)
C80.0199 (9)0.0144 (8)0.0231 (9)0.0051 (7)0.0075 (7)0.0061 (7)
C90.0203 (9)0.0170 (8)0.0263 (9)0.0060 (7)0.0106 (7)0.0075 (7)
C100.0253 (10)0.0208 (9)0.0308 (10)0.0118 (8)0.0134 (8)0.0103 (8)
C110.0263 (10)0.0213 (9)0.0406 (12)0.0105 (8)0.0136 (9)0.0082 (9)
C120.0397 (13)0.0257 (10)0.0477 (13)0.0180 (10)0.0223 (11)0.0128 (10)
C130.0365 (12)0.0351 (11)0.0456 (13)0.0238 (10)0.0219 (10)0.0192 (10)
C140.0260 (11)0.0378 (13)0.0644 (17)0.0176 (10)0.0152 (11)0.0166 (12)
C150.0255 (11)0.0243 (10)0.0644 (16)0.0094 (9)0.0139 (11)0.0116 (11)
C160.0244 (10)0.0247 (9)0.0276 (9)0.0103 (8)0.0127 (8)0.0124 (8)
C170.0304 (11)0.0290 (10)0.0280 (10)0.0097 (9)0.0138 (9)0.0115 (8)
C180.0472 (14)0.0384 (12)0.0341 (11)0.0148 (11)0.0242 (11)0.0134 (10)
C190.0537 (15)0.0356 (12)0.0253 (10)0.0175 (11)0.0183 (10)0.0094 (9)
C200.0410 (13)0.0260 (10)0.0264 (10)0.0099 (9)0.0094 (9)0.0064 (8)
C210.0297 (11)0.0239 (9)0.0274 (10)0.0080 (8)0.0100 (8)0.0081 (8)
C220.0249 (10)0.0234 (9)0.0247 (9)0.0094 (8)0.0099 (8)0.0090 (8)
C230.0189 (9)0.0215 (8)0.0232 (9)0.0077 (7)0.0087 (7)0.0078 (7)
C240.0194 (9)0.0193 (8)0.0278 (9)0.0052 (7)0.0087 (8)0.0083 (7)
C250.0213 (9)0.0240 (9)0.0308 (10)0.0029 (8)0.0110 (8)0.0043 (8)
C260.0244 (10)0.0321 (11)0.0312 (10)0.0057 (9)0.0112 (9)0.0082 (9)
C270.0288 (11)0.0371 (12)0.0330 (11)0.0042 (10)0.0108 (9)0.0029 (10)
C280.0335 (12)0.0298 (11)0.0434 (14)0.0027 (10)0.0131 (11)0.0028 (10)
C290.0407 (14)0.0292 (11)0.0513 (15)0.0024 (10)0.0201 (12)0.0076 (11)
C300.0339 (12)0.0277 (10)0.0370 (12)0.0011 (9)0.0163 (10)0.0072 (9)
N90.0493 (14)0.0616 (16)0.0837 (19)0.0229 (13)0.0305 (14)0.0451 (15)
C330.064 (2)0.104 (3)0.119 (3)0.049 (2)0.062 (2)0.089 (3)
O30.058 (3)0.091 (6)0.074 (5)0.012 (4)0.048 (4)0.037 (5)
C310.069 (10)0.143 (13)0.140 (13)0.023 (9)0.065 (9)0.063 (10)
C320.130 (10)0.151 (13)0.056 (6)0.048 (9)0.043 (6)0.001 (7)
O3X0.038 (2)0.069 (4)0.064 (4)0.006 (2)0.030 (3)0.033 (4)
C31X0.049 (5)0.063 (4)0.052 (4)0.042 (4)0.037 (4)0.047 (4)
C32X0.070 (5)0.054 (4)0.048 (5)0.021 (4)0.003 (4)0.004 (4)
Geometric parameters (Å, º) top
Ni1—N22.0342 (15)C14—C151.391 (3)
Ni1—N62.0373 (15)C14—H14A0.9500
Ni1—O12.1886 (13)C15—H15A0.9500
Ni1—O22.2441 (13)C16—C231.475 (3)
Ni1—S12.3564 (5)C17—C181.381 (3)
Ni1—S22.3866 (5)C17—C221.405 (3)
S1—C91.7053 (19)C18—C191.390 (3)
S2—C241.728 (2)C18—H18A0.9500
O1—C11.255 (2)C19—C201.382 (3)
O2—C161.248 (2)C19—H19A0.9500
N1—C11.347 (2)C20—C211.392 (3)
N1—C21.414 (2)C20—H20A0.9500
N1—H1N10.79 (3)C21—C221.388 (3)
N2—C81.315 (2)C21—H21A0.9500
N2—N31.328 (2)C22—C231.451 (3)
N3—C91.371 (2)C25—C261.386 (3)
N4—C91.352 (2)C25—C301.403 (3)
N4—C101.412 (2)C26—C271.385 (3)
N4—H1N40.81 (3)C26—H26A0.9500
N5—C161.352 (3)C27—C281.384 (4)
N5—C171.414 (3)C27—H27A0.9500
N5—H1N50.89 (3)C28—C291.383 (4)
N6—C231.302 (2)C28—H28A0.9500
N6—N71.342 (2)C29—C301.390 (3)
N7—C241.335 (2)C29—H29A0.9500
N8—C241.353 (2)C30—H30A0.9500
N8—C251.418 (3)N9—C331.347 (4)
N8—H1N80.85 (3)N9—C32X1.381 (9)
C1—C81.464 (2)N9—C31X1.408 (10)
C2—C31.381 (3)N9—C311.429 (16)
C2—C71.410 (2)N9—C321.619 (12)
C3—C41.393 (3)C33—O3X1.229 (6)
C3—H3A0.9500C33—O31.298 (8)
C4—C51.392 (3)C33—H33A0.9500
C4—H4A0.9500C33—H33B0.9600
C5—C61.400 (3)C31—H31A0.9800
C5—H5A0.9500C31—H31B0.9800
C6—C71.389 (3)C31—H31C0.9800
C6—H6A0.9500C32—H32A0.9800
C7—C81.445 (3)C32—H32B0.9800
C10—C151.386 (3)C32—H32C0.9800
C10—C111.396 (3)C31X—H31D0.9800
C11—C121.386 (3)C31X—H31E0.9800
C11—H11A0.9500C31X—H31F0.9800
C12—C131.379 (3)C32X—H32D0.9800
C12—H12A0.9500C32X—H32E0.9800
C13—C141.367 (3)C32X—H32F0.9800
C13—H13A0.9500
N2—Ni1—N6163.87 (6)C10—C15—H15A120.1
N2—Ni1—O180.64 (5)C14—C15—H15A120.1
N6—Ni1—O189.97 (5)O2—C16—N5128.61 (19)
N2—Ni1—O286.61 (5)O2—C16—C23124.53 (17)
N6—Ni1—O279.65 (5)N5—C16—C23106.86 (17)
O1—Ni1—O286.10 (5)C18—C17—C22122.1 (2)
N2—Ni1—S180.27 (4)C18—C17—N5128.4 (2)
N6—Ni1—S1109.33 (4)C22—C17—N5109.45 (18)
O1—Ni1—S1160.66 (4)C17—C18—C19117.1 (2)
O2—Ni1—S195.85 (4)C17—C18—H18A121.4
N2—Ni1—S2113.35 (5)C19—C18—H18A121.4
N6—Ni1—S279.44 (4)C20—C19—C18121.4 (2)
O1—Ni1—S289.75 (4)C20—C19—H19A119.3
O2—Ni1—S2158.67 (4)C18—C19—H19A119.3
S1—Ni1—S294.949 (19)C19—C20—C21121.3 (2)
C9—S1—Ni196.51 (6)C19—C20—H20A119.3
C24—S2—Ni195.92 (7)C21—C20—H20A119.3
C1—O1—Ni1105.85 (11)C22—C21—C20118.1 (2)
C16—O2—Ni1104.98 (12)C22—C21—H21A121.0
C1—N1—C2110.03 (15)C20—C21—H21A121.0
C1—N1—H1N1125 (2)C21—C22—C17119.86 (19)
C2—N1—H1N1125 (2)C21—C22—C23134.39 (19)
C8—N2—N3119.43 (15)C17—C22—C23105.75 (17)
C8—N2—Ni1113.80 (12)N6—C23—C22137.10 (18)
N3—N2—Ni1126.43 (12)N6—C23—C16115.45 (16)
N2—N3—C9111.47 (15)C22—C23—C16107.37 (16)
C9—N4—C10133.07 (18)N7—C24—N8117.60 (17)
C9—N4—H1N4113.1 (17)N7—C24—S2125.57 (15)
C10—N4—H1N4113.6 (17)N8—C24—S2116.77 (15)
C16—N5—C17110.54 (17)C26—C25—C30119.45 (19)
C16—N5—H1N5124.5 (19)C26—C25—N8124.72 (19)
C17—N5—H1N5124.9 (19)C30—C25—N8115.81 (19)
C23—N6—N7117.97 (16)C27—C26—C25120.1 (2)
C23—N6—Ni1114.66 (12)C27—C26—H26A120.0
N7—N6—Ni1127.13 (12)C25—C26—H26A120.0
C24—N7—N6111.61 (15)C26—C27—C28120.8 (2)
C24—N8—C25130.78 (18)C26—C27—H27A119.6
C24—N8—H1N8112.5 (17)C28—C27—H27A119.6
C25—N8—H1N8116.5 (17)C29—C28—C27119.4 (2)
O1—C1—N1127.81 (17)C29—C28—H28A120.3
O1—C1—C8124.69 (16)C27—C28—H28A120.3
N1—C1—C8107.50 (16)C28—C29—C30120.6 (2)
C3—C2—C7122.46 (17)C28—C29—H29A119.7
C3—C2—N1128.16 (17)C30—C29—H29A119.7
C7—C2—N1109.37 (16)C29—C30—C25119.6 (2)
C2—C3—C4117.01 (18)C29—C30—H30A120.2
C2—C3—H3A121.5C25—C30—H30A120.2
C4—C3—H3A121.5C33—N9—C32X111.8 (6)
C5—C4—C3121.63 (19)C33—N9—C31X121.5 (4)
C5—C4—H4A119.2C32X—N9—C31X126.7 (6)
C3—C4—H4A119.2C33—N9—C31119.3 (8)
C4—C5—C6120.96 (18)C32X—N9—C31128.6 (10)
C4—C5—H5A119.5C33—N9—C32132.9 (6)
C6—C5—H5A119.5C31X—N9—C32104.9 (7)
C7—C6—C5118.11 (17)C31—N9—C32107.6 (9)
C7—C6—H6A120.9O3X—C33—N9140.3 (5)
C5—C6—H6A120.9O3—C33—N9107.0 (6)
C6—C7—C2119.83 (17)O3X—C33—H33A89.3
C6—C7—C8134.55 (17)O3—C33—H33A126.5
C2—C7—C8105.60 (15)N9—C33—H33A126.5
N2—C8—C7137.86 (17)O3X—C33—H33B109.8
N2—C8—C1114.74 (16)O3—C33—H33B133.6
C7—C8—C1107.39 (15)N9—C33—H33B109.9
N4—C9—N3110.48 (16)N9—C31—H31A109.5
N4—C9—S1124.46 (14)N9—C31—H31B109.5
N3—C9—S1125.06 (14)N9—C31—H31C109.5
C15—C10—C11118.47 (18)N9—C32—H32A109.5
C15—C10—N4125.52 (18)N9—C32—H32B109.5
C11—C10—N4115.98 (18)N9—C32—H32C109.5
C12—C11—C10120.7 (2)N9—C31X—H31D109.5
C12—C11—H11A119.6N9—C31X—H31E109.5
C10—C11—H11A119.6H31D—C31X—H31E109.5
C13—C12—C11120.4 (2)N9—C31X—H31F109.5
C13—C12—H12A119.8H31D—C31X—H31F109.5
C11—C12—H12A119.8H31E—C31X—H31F109.5
C14—C13—C12119.0 (2)N9—C32X—H32D109.5
C14—C13—H13A120.5N9—C32X—H32E109.5
C12—C13—H13A120.5H32D—C32X—H32E109.5
C13—C14—C15121.6 (2)N9—C32X—H32F109.5
C13—C14—H14A119.2H32D—C32X—H32F109.5
C15—C14—H14A119.2H32E—C32X—H32F109.5
C10—C15—C14119.8 (2)
N2—Ni1—S1—C93.18 (8)O1—C1—C8—C7176.31 (18)
N6—Ni1—S1—C9163.42 (8)N1—C1—C8—C73.1 (2)
O1—Ni1—S1—C912.56 (14)C10—N4—C9—N3175.2 (2)
O2—Ni1—S1—C982.36 (7)C10—N4—C9—S15.4 (3)
S2—Ni1—S1—C9116.05 (7)N2—N3—C9—N4179.52 (16)
N2—Ni1—S2—C24173.88 (8)N2—N3—C9—S11.1 (2)
N6—Ni1—S2—C244.18 (7)Ni1—S1—C9—N4177.06 (16)
O1—Ni1—S2—C2494.19 (7)Ni1—S1—C9—N32.25 (17)
O2—Ni1—S2—C2415.62 (13)C9—N4—C10—C1511.0 (4)
S1—Ni1—S2—C24104.59 (6)C9—N4—C10—C11170.9 (2)
N2—Ni1—O1—C12.40 (12)C15—C10—C11—C120.1 (3)
N6—Ni1—O1—C1164.43 (13)N4—C10—C11—C12178.4 (2)
O2—Ni1—O1—C184.80 (12)C10—C11—C12—C130.4 (4)
S1—Ni1—O1—C111.8 (2)C11—C12—C13—C140.4 (4)
S2—Ni1—O1—C1116.13 (12)C12—C13—C14—C150.1 (4)
N2—Ni1—O2—C16164.17 (12)C11—C10—C15—C140.1 (4)
N6—Ni1—O2—C167.35 (12)N4—C10—C15—C14178.0 (2)
O1—Ni1—O2—C1683.33 (12)C13—C14—C15—C100.1 (4)
S1—Ni1—O2—C16115.98 (11)Ni1—O2—C16—N5171.38 (18)
S2—Ni1—O2—C164.09 (19)Ni1—O2—C16—C238.4 (2)
N6—Ni1—N2—C850.5 (3)C17—N5—C16—O2179.06 (19)
O1—Ni1—N2—C84.60 (13)C17—N5—C16—C231.1 (2)
O2—Ni1—N2—C882.01 (13)C16—N5—C17—C18179.1 (2)
S1—Ni1—N2—C8178.54 (13)C16—N5—C17—C220.1 (2)
S2—Ni1—N2—C890.24 (13)C22—C17—C18—C191.2 (3)
N6—Ni1—N2—N3122.6 (2)N5—C17—C18—C19177.9 (2)
O1—Ni1—N2—N3177.76 (16)C17—C18—C19—C201.0 (3)
O2—Ni1—N2—N391.15 (15)C18—C19—C20—C210.2 (4)
S1—Ni1—N2—N35.38 (14)C19—C20—C21—C220.6 (3)
S2—Ni1—N2—N396.60 (14)C20—C21—C22—C170.5 (3)
C8—N2—N3—C9178.00 (16)C20—C21—C22—C23179.3 (2)
Ni1—N2—N3—C95.2 (2)C18—C17—C22—C210.4 (3)
N2—Ni1—N6—C2326.1 (3)N5—C17—C22—C21178.82 (18)
O1—Ni1—N6—C2380.17 (13)C18—C17—C22—C23179.8 (2)
O2—Ni1—N6—C235.88 (12)N5—C17—C22—C231.0 (2)
S1—Ni1—N6—C2398.50 (13)N7—N6—C23—C222.1 (3)
S2—Ni1—N6—C23169.91 (13)Ni1—N6—C23—C22172.66 (19)
N2—Ni1—N6—N7148.11 (19)N7—N6—C23—C16178.39 (15)
O1—Ni1—N6—N794.07 (14)Ni1—N6—C23—C163.6 (2)
O2—Ni1—N6—N7179.88 (15)C21—C22—C23—N65.4 (4)
S1—Ni1—N6—N787.26 (14)C17—C22—C23—N6174.8 (2)
S2—Ni1—N6—N74.33 (13)C21—C22—C23—C16178.1 (2)
C23—N6—N7—C24172.15 (16)C17—C22—C23—C161.6 (2)
Ni1—N6—N7—C241.9 (2)O2—C16—C23—N64.2 (3)
Ni1—O1—C1—N1179.24 (18)N5—C16—C23—N6175.61 (16)
Ni1—O1—C1—C80.1 (2)O2—C16—C23—C22178.46 (18)
C2—N1—C1—O1176.12 (19)N5—C16—C23—C221.7 (2)
C2—N1—C1—C83.3 (2)N6—N7—C24—N8179.18 (16)
C1—N1—C2—C3177.1 (2)N6—N7—C24—S23.5 (2)
C1—N1—C2—C72.3 (2)C25—N8—C24—N74.8 (3)
C7—C2—C3—C40.1 (3)C25—N8—C24—S2172.74 (17)
N1—C2—C3—C4179.3 (2)Ni1—S2—C24—N75.77 (17)
C2—C3—C4—C50.2 (3)Ni1—S2—C24—N8176.93 (14)
C3—C4—C5—C60.3 (3)C24—N8—C25—C2624.4 (3)
C4—C5—C6—C70.8 (3)C24—N8—C25—C30157.2 (2)
C5—C6—C7—C20.8 (3)C30—C25—C26—C270.7 (3)
C5—C6—C7—C8179.1 (2)N8—C25—C26—C27179.1 (2)
C3—C2—C7—C60.4 (3)C25—C26—C27—C280.0 (4)
N1—C2—C7—C6178.94 (17)C26—C27—C28—C290.9 (4)
C3—C2—C7—C8179.16 (18)C27—C28—C29—C301.1 (4)
N1—C2—C7—C80.2 (2)C28—C29—C30—C250.5 (4)
N3—N2—C8—C70.8 (3)C26—C25—C30—C290.5 (3)
Ni1—N2—C8—C7174.5 (2)N8—C25—C30—C29179.0 (2)
N3—N2—C8—C1179.47 (16)C32X—N9—C33—O3X13.7 (9)
Ni1—N2—C8—C15.8 (2)C31X—N9—C33—O3X165.7 (8)
C6—C7—C8—N23.5 (4)C31—N9—C33—O3X160.5 (10)
C2—C7—C8—N2178.0 (2)C32—N9—C33—O3X26.4 (12)
C6—C7—C8—C1176.7 (2)C32X—N9—C33—O316.0 (6)
C2—C7—C8—C11.7 (2)C31X—N9—C33—O3164.6 (5)
O1—C1—C8—N23.9 (3)C31—N9—C33—O3169.7 (9)
N1—C1—C8—N2176.67 (16)C32—N9—C33—O33.3 (10)
Hydrogen-bond geometry (Å, º) top
Cg5, Cg7, Cg9 and Cg10 are the centroids of the N1/C1/C8/C7/C2, C2–C7, C17–C22 and C25–C30 rings, respectively.
D—H···AD—HH···AD···AD—H···A
N8—H1N8···S2i0.86 (2)2.48 (3)3.301 (2)159 (2)
N1—H1N1···O1ii0.79 (4)2.04 (4)2.811 (2)165 (4)
N5—H1N5···O3Xiii0.89 (4)1.84 (4)2.729 (9)173 (3)
N4—H1N4···O2iv0.82 (3)2.22 (3)3.006 (3)161 (2)
C3—H3A···N7ii0.952.563.500 (3)173
C11—H11A···O2iv0.952.553.349 (3)142
C15—H15A···S10.952.533.194 (3)127
C20—H20A···S1v0.952.713.443 (2)135
C26—H26A···N70.952.352.900 (3)116
C30—H30A···S2i0.952.843.551 (2)132
C32X—H32D···O3X0.982.462.859 (14)104
C31X—H31E···Cg9vi0.982.973.567 (11)121
C31X—H31F···Cg7iv0.982.793.460 (10)126
C32X—H32D···Cg10vii0.982.913.769 (12)147
C31—H31B···Cg9vi0.982.983.66 (2)128
C31—H31C···Cg7iv0.982.783.47 (2)127
C32—H32B···Cg5iv0.982.823.577 (16)135
Symmetry codes: (i) x+1, y, z+1; (ii) x+2, y, z+1; (iii) x+2, y+1, z; (iv) x+2, y+1, z+1; (v) x+1, y, z; (vi) x, y+1, z; (vii) x+1, y+1, z.

Experimental details

Crystal data
Chemical formula[Ni(C15H11N4OS)2]·C3H7NO
Mr722.48
Crystal system, space groupTriclinic, P1
Temperature (K)100
a, b, c (Å)12.2491 (2), 12.3170 (3), 13.1142 (2)
α, β, γ (°)104.854 (1), 112.943 (1), 102.798 (1)
V3)1642.31 (5)
Z2
Radiation typeMo Kα
µ (mm1)0.77
Crystal size (mm)0.45 × 0.15 × 0.13
Data collection
DiffractometerBruker APEXII CCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2005)
Tmin, Tmax0.723, 0.906
No. of measured, independent and
observed [I > 2σ(I)] reflections
34412, 9435, 7397
Rint0.033
(sin θ/λ)max1)0.704
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.041, 0.107, 1.03
No. of reflections9435
No. of parameters481
No. of restraints25
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.63, 0.37

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXS97(Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Selected bond lengths (Å) top
Ni1—N22.0342 (15)Ni1—O22.2441 (13)
Ni1—N62.0373 (15)Ni1—S12.3564 (5)
Ni1—O12.1886 (13)Ni1—S22.3866 (5)
Hydrogen-bond geometry (Å, º) top
Cg5, Cg7, Cg9 and Cg10 are the centroids of the N1/C1/C8/C7/C2, C2–C7, C17–C22 and C25–C30 rings, respectively.
D—H···AD—HH···AD···AD—H···A
N8—H1N8···S2i0.86 (2)2.48 (3)3.301 (2)159 (2)
N1—H1N1···O1ii0.79 (4)2.04 (4)2.811 (2)165 (4)
N5—H1N5···O3Xiii0.89 (4)1.84 (4)2.729 (9)173 (3)
N4—H1N4···O2iv0.82 (3)2.22 (3)3.006 (3)161 (2)
C3—H3A···N7ii0.95002.56003.500 (3)173.00
C11—H11A···O2iv0.95002.55003.349 (3)142.00
C15—H15A···S10.95002.53003.194 (3)127.00
C20—H20A···S1v0.95002.71003.443 (2)135.00
C30—H30A···S2i0.95002.84003.551 (2)132.00
C31X—H31E···Cg9vi0.98002.973.567 (11)121
C31X—H31F···Cg7iv0.98002.793.460 (10)126
C32X—H32D···Cg10vii0.98002.913.769 (12)147
C31—H31B···Cg9vi0.98002.983.66 (2)128
C31—H31C···Cg7iv0.98002.783.47 (2)127
C32—H32B···Cg5iv0.98002.823.577 (16)135
Symmetry codes: (i) x+1, y, z+1; (ii) x+2, y, z+1; (iii) x+2, y+1, z; (iv) x+2, y+1, z+1; (v) x+1, y, z; (vi) x, y+1, z; (vii) x+1, y+1, z.
 

Footnotes

Thomson Reuters ResearcherID: E-9395-2011.

§Thomson Reuters ResearcherID: A-3561-2009.

Acknowledgements

The authors thank the Malaysian Government and Universiti Sains Malaysia for the RU research grant (1001/PKIMIA/815067). AQA thanks the Ministry of Higher Education and the University of Sabha (Libya) for a scholarship.

References

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Volume 68| Part 5| May 2012| Pages m538-m539
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