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

Ali, A.Q.; Eltayeb, N.E.; Teoh, S.G.; Salhin, A.; Fun, H.-K.

doi:10.1107/S1600536812012834

metal-organic compounds

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ISSN: 2056-9890

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

doi:10.1107/S1600536812012834

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

Amna Qasem Ali,^a,^b Naser Eltaher Eltayeb,^c ‡ Siang Guan Teoh,^a ^* Abdussalam Salhin ^a and Hoong-Kun Fun ^d §

^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 Ni^II complex molecule and one disordered dimethylformamide solvent molecule. The Ni^II 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 ,b , 2012a ,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

Crystal data

[Ni(C₁₅H₁₁N₄OS)₂]·C₃H₇NO
M_r = 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 ) T_min = 0.723, T_max = 0.906
34412 measured reflections
9435 independent reflections
7397 reflections with I > 2σ(I)
R_int = 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
Δρ_max = 0.63 e Å⁻³
Δρ_min = −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	D⋯A	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⋯O2^iv	0.82 (3)	2.22 (3)	3.006 (3)	161 (2)
C3—H3A⋯N7ⁱⁱ	0.95	2.56	3.500 (3)	173
C11—H11A⋯O2^iv	0.95	2.55	3.349 (3)	142
C15—H15A⋯S1	0.95	2.53	3.194 (3)	127
C20—H20A⋯S1^v	0.95	2.71	3.443 (2)	135
C30—H30A⋯S2ⁱ	0.95	2.84	3.551 (2)	132
C31X—H31E⋯Cg9^vi	0.98	2.97	3.567 (11)	121
C31X—H31F⋯Cg7^iv	0.98	2.79	3.460 (10)	126
C32X—H32D⋯Cg10^vii	0.98	2.91	3.769 (12)	147
C31—H31B⋯Cg9^vi	0.98	2.98	3.66 (2)	128
C31—H31C⋯Cg7^iv	0.98	2.78	3.47 (2)	127
C32—H32B⋯Cg5^iv	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); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT; 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 and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812012834/zj2062sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812012834/zj2062Isup2.hkl

checkCIF report

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 Ni^II complex, [Ni(C₁₅H₁₁N₄OS)₂] and one solvent molecule, [C₃H₇NO], which displays disorder. Ni^II 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.

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

	Fig. 1. The molecular structure of the title compound, with 50% probability displacement ellipsoids and the atom-numbering scheme.
	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]·C₃H₇NO	Z = 2
M_r = 722.48	F(000) = 748
Triclinic, P1	D_x = 1.461 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 12.2491 (2) Å	Cell parameters from 9906 reflections
b = 12.3170 (3) Å	θ = 2.7–29.9°
c = 13.1142 (2) Å	µ = 0.77 mm⁻¹
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 tube	7397 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.033
ϕ and ω scans	θ_max = 30.0°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −16→16
T_min = 0.723, T_max = 0.906	k = −16→17
34412 measured reflections	l = −18→18

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.107	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ²(F_o²) + (0.0498P)² + 0.8476P] where P = (F_o² + 2F_c²)/3
9435 reflections	(Δ/σ)_max = 0.002
481 parameters	Δρ_max = 0.63 e Å⁻³
25 restraints	Δρ_min = −0.37 e Å⁻³

Crystal data top

[Ni(C₁₅H₁₁N₄OS)₂]·C₃H₇NO	γ = 102.798 (1)°
M_r = 722.48	V = 1642.31 (5) Å³
Triclinic, P1	Z = 2
a = 12.2491 (2) Å	Mo Kα radiation
b = 12.3170 (3) Å	µ = 0.77 mm⁻¹
c = 13.1142 (2) Å	T = 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)
T_min = 0.723, T_max = 0.906	R_int = 0.033
34412 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	25 restraints
wR(F²) = 0.107	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	Δρ_max = 0.63 e Å⁻³
9435 reflections	Δρ_min = −0.37 e Å⁻³
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

	x	y	z	U_iso*/U_eq	Occ. (<1)
Ni1	0.78451 (2)	0.19687 (2)	0.41425 (2)	0.01968 (7)
S1	0.70744 (4)	0.35633 (4)	0.42739 (5)	0.02561 (11)
S2	0.65024 (5)	0.08658 (4)	0.47337 (4)	0.02594 (11)
O1	0.90909 (12)	0.09464 (11)	0.45887 (12)	0.0248 (3)
O2	0.87054 (12)	0.23656 (11)	0.29881 (12)	0.0241 (3)
N1	1.12110 (15)	0.15001 (14)	0.60044 (15)	0.0242 (3)
N2	0.94274 (14)	0.33207 (13)	0.55479 (14)	0.0201 (3)
N3	0.95747 (15)	0.44742 (13)	0.59700 (14)	0.0223 (3)
N4	0.86366 (17)	0.58352 (14)	0.58507 (16)	0.0260 (4)
N5	0.83284 (18)	0.11914 (17)	0.10848 (16)	0.0309 (4)
N6	0.66127 (14)	0.05595 (13)	0.25591 (14)	0.0199 (3)
N7	0.55864 (15)	−0.03271 (14)	0.23367 (14)	0.0223 (3)
N8	0.44456 (16)	−0.10476 (15)	0.32126 (16)	0.0271 (4)
C1	1.01396 (18)	0.17003 (16)	0.54342 (17)	0.0220 (4)
C2	1.22052 (18)	0.26024 (16)	0.68514 (17)	0.0228 (4)
C3	1.34585 (19)	0.27929 (18)	0.75792 (18)	0.0272 (4)
H3A	1.3761	0.2145	0.7565	0.033*
C4	1.42602 (19)	0.39775 (18)	0.83346 (19)	0.0302 (4)
H4A	1.5128	0.4140	0.8849	0.036*
C5	1.38212 (19)	0.49286 (18)	0.83545 (18)	0.0286 (4)
H5A	1.4392	0.5726	0.8883	0.034*
C6	1.25508 (18)	0.47278 (17)	0.76076 (17)	0.0247 (4)
H6A	1.2254	0.5378	0.7614	0.030*
C7	1.17367 (18)	0.35500 (16)	0.68558 (16)	0.0220 (4)
C8	1.04087 (17)	0.29907 (15)	0.59716 (16)	0.0205 (3)
C9	0.84681 (17)	0.46578 (16)	0.54011 (17)	0.0217 (4)
C10	0.78016 (19)	0.64753 (17)	0.56415 (18)	0.0248 (4)
C11	0.8371 (2)	0.77289 (18)	0.6156 (2)	0.0306 (4)
H11A	0.9271	0.8096	0.6597	0.037*
C12	0.7638 (2)	0.8445 (2)	0.6031 (2)	0.0362 (5)
H12A	0.8039	0.9297	0.6383	0.043*
C13	0.6330 (2)	0.7927 (2)	0.5401 (2)	0.0353 (5)
H13A	0.5826	0.8416	0.5318	0.042*
C14	0.5770 (2)	0.6699 (2)	0.4895 (3)	0.0444 (6)
H14A	0.4869	0.6340	0.4459	0.053*
C15	0.6487 (2)	0.5963 (2)	0.5005 (2)	0.0418 (6)
H15A	0.6076	0.5112	0.4645	0.050*
C16	0.80929 (18)	0.14680 (17)	0.20257 (17)	0.0246 (4)
C17	0.7387 (2)	0.00967 (19)	0.01605 (18)	0.0292 (4)
C18	0.7279 (2)	−0.0482 (2)	−0.0946 (2)	0.0383 (5)
H18A	0.7892	−0.0172	−0.1171	0.046*
C19	0.6232 (2)	−0.1538 (2)	−0.1715 (2)	0.0385 (5)
H19A	0.6121	−0.1951	−0.2488	0.046*
C20	0.5349 (2)	−0.2000 (2)	−0.13809 (19)	0.0347 (5)
H20A	0.4647	−0.2725	−0.1927	0.042*
C21	0.5470 (2)	−0.14246 (18)	−0.02595 (18)	0.0289 (4)
H21A	0.4864	−0.1750	−0.0032	0.035*
C22	0.64997 (19)	−0.03614 (17)	0.05159 (17)	0.0248 (4)
C23	0.69379 (17)	0.04848 (16)	0.17166 (16)	0.0217 (4)
C24	0.54556 (18)	−0.02168 (16)	0.33181 (17)	0.0236 (4)
C25	0.35014 (19)	−0.21055 (18)	0.22267 (18)	0.0282 (4)
C26	0.3149 (2)	−0.2297 (2)	0.10356 (19)	0.0317 (4)
H26A	0.3559	−0.1699	0.0835	0.038*
C27	0.2200 (2)	−0.3359 (2)	0.0138 (2)	0.0381 (5)
H27A	0.1963	−0.3484	−0.0676	0.046*
C28	0.1592 (2)	−0.4240 (2)	0.0413 (2)	0.0438 (6)
H28A	0.0950	−0.4971	−0.0207	0.053*
C29	0.1926 (2)	−0.4047 (2)	0.1598 (2)	0.0456 (6)
H29A	0.1500	−0.4644	0.1790	0.055*
C30	0.2880 (2)	−0.2989 (2)	0.2512 (2)	0.0361 (5)
H30A	0.3109	−0.2865	0.3325	0.043*
N9	0.8695 (2)	0.7307 (2)	0.0180 (3)	0.0608 (7)
C33	0.8769 (3)	0.7217 (4)	−0.0834 (4)	0.0751 (11)
H33A	0.8143	0.6683	−0.1624	0.090*	0.486 (15)
H33B	0.7932	0.6948	−0.1495	0.090*	0.514 (15)
O3	0.9859 (7)	0.7999 (10)	−0.0528 (10)	0.070 (2)	0.486 (15)
C31	0.7511 (15)	0.6693 (17)	0.0101 (17)	0.113 (6)	0.486 (15)
H31A	0.6901	0.6178	−0.0736	0.169*	0.486 (15)
H31B	0.7179	0.7284	0.0404	0.169*	0.486 (15)
H31C	0.7640	0.6197	0.0583	0.169*	0.486 (15)
C32	0.9682 (15)	0.8108 (15)	0.1582 (11)	0.140 (7)	0.486 (15)
H32A	1.0540	0.8423	0.1681	0.210*	0.486 (15)
H32B	0.9671	0.7606	0.2052	0.210*	0.486 (15)
H32C	0.9430	0.8781	0.1861	0.210*	0.486 (15)
O3X	0.9563 (5)	0.7356 (8)	−0.1188 (8)	0.056 (2)	0.514 (15)
C31X	0.7529 (9)	0.6800 (9)	0.0153 (8)	0.040 (2)	0.514 (15)
H31D	0.6858	0.6375	−0.0680	0.061*	0.514 (15)
H31E	0.7319	0.7441	0.0564	0.061*	0.514 (15)
H31F	0.7600	0.6232	0.0558	0.061*	0.514 (15)
C32X	0.9868 (9)	0.7923 (8)	0.1185 (9)	0.070 (3)	0.514 (15)
H32D	1.0535	0.7815	0.0979	0.105*	0.514 (15)
H32E	0.9902	0.7609	0.1808	0.105*	0.514 (15)
H32F	1.0001	0.8782	0.1483	0.105*	0.514 (15)
H1N8	0.442 (2)	−0.092 (2)	0.388 (2)	0.037 (7)*
H1N1	1.127 (3)	0.086 (3)	0.590 (2)	0.045 (8)*
H1N5	0.901 (3)	0.162 (3)	0.107 (3)	0.055 (8)*
H1N4	0.938 (2)	0.627 (2)	0.630 (2)	0.033 (7)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ni1	0.01728 (12)	0.01467 (11)	0.02259 (12)	0.00379 (9)	0.00726 (9)	0.00553 (9)
S1	0.0183 (2)	0.0182 (2)	0.0310 (2)	0.00567 (18)	0.00575 (19)	0.00578 (19)
S2	0.0247 (2)	0.0222 (2)	0.0242 (2)	0.00144 (19)	0.0111 (2)	0.00564 (18)
O1	0.0202 (7)	0.0157 (6)	0.0281 (7)	0.0044 (5)	0.0050 (6)	0.0051 (5)
O2	0.0210 (7)	0.0196 (6)	0.0250 (7)	0.0007 (5)	0.0099 (6)	0.0057 (5)
N1	0.0217 (8)	0.0147 (7)	0.0282 (8)	0.0075 (6)	0.0055 (7)	0.0054 (6)
N2	0.0200 (8)	0.0149 (7)	0.0234 (7)	0.0055 (6)	0.0090 (6)	0.0069 (6)
N3	0.0204 (8)	0.0141 (7)	0.0272 (8)	0.0057 (6)	0.0081 (6)	0.0056 (6)
N4	0.0191 (8)	0.0163 (7)	0.0359 (9)	0.0069 (7)	0.0087 (7)	0.0065 (7)
N5	0.0284 (9)	0.0325 (9)	0.0300 (9)	0.0049 (8)	0.0165 (8)	0.0103 (8)
N6	0.0156 (7)	0.0163 (7)	0.0244 (8)	0.0043 (6)	0.0075 (6)	0.0073 (6)
N7	0.0182 (8)	0.0192 (7)	0.0256 (8)	0.0038 (6)	0.0094 (6)	0.0071 (6)
N8	0.0243 (9)	0.0248 (8)	0.0254 (8)	0.0006 (7)	0.0117 (7)	0.0065 (7)
C1	0.0213 (9)	0.0161 (8)	0.0246 (9)	0.0070 (7)	0.0078 (7)	0.0064 (7)
C2	0.0216 (9)	0.0174 (8)	0.0240 (9)	0.0062 (7)	0.0074 (7)	0.0060 (7)
C3	0.0243 (10)	0.0220 (9)	0.0305 (10)	0.0101 (8)	0.0081 (8)	0.0092 (8)
C4	0.0219 (10)	0.0269 (10)	0.0308 (10)	0.0064 (8)	0.0043 (8)	0.0095 (8)
C5	0.0238 (10)	0.0200 (9)	0.0281 (10)	0.0027 (8)	0.0045 (8)	0.0054 (8)
C6	0.0251 (10)	0.0182 (8)	0.0262 (9)	0.0067 (8)	0.0096 (8)	0.0066 (7)
C7	0.0209 (9)	0.0187 (8)	0.0228 (9)	0.0067 (7)	0.0075 (7)	0.0076 (7)
C8	0.0199 (9)	0.0144 (8)	0.0231 (9)	0.0051 (7)	0.0075 (7)	0.0061 (7)
C9	0.0203 (9)	0.0170 (8)	0.0263 (9)	0.0060 (7)	0.0106 (7)	0.0075 (7)
C10	0.0253 (10)	0.0208 (9)	0.0308 (10)	0.0118 (8)	0.0134 (8)	0.0103 (8)
C11	0.0263 (10)	0.0213 (9)	0.0406 (12)	0.0105 (8)	0.0136 (9)	0.0082 (9)
C12	0.0397 (13)	0.0257 (10)	0.0477 (13)	0.0180 (10)	0.0223 (11)	0.0128 (10)
C13	0.0365 (12)	0.0351 (11)	0.0456 (13)	0.0238 (10)	0.0219 (10)	0.0192 (10)
C14	0.0260 (11)	0.0378 (13)	0.0644 (17)	0.0176 (10)	0.0152 (11)	0.0166 (12)
C15	0.0255 (11)	0.0243 (10)	0.0644 (16)	0.0094 (9)	0.0139 (11)	0.0116 (11)
C16	0.0244 (10)	0.0247 (9)	0.0276 (9)	0.0103 (8)	0.0127 (8)	0.0124 (8)
C17	0.0304 (11)	0.0290 (10)	0.0280 (10)	0.0097 (9)	0.0138 (9)	0.0115 (8)
C18	0.0472 (14)	0.0384 (12)	0.0341 (11)	0.0148 (11)	0.0242 (11)	0.0134 (10)
C19	0.0537 (15)	0.0356 (12)	0.0253 (10)	0.0175 (11)	0.0183 (10)	0.0094 (9)
C20	0.0410 (13)	0.0260 (10)	0.0264 (10)	0.0099 (9)	0.0094 (9)	0.0064 (8)
C21	0.0297 (11)	0.0239 (9)	0.0274 (10)	0.0080 (8)	0.0100 (8)	0.0081 (8)
C22	0.0249 (10)	0.0234 (9)	0.0247 (9)	0.0094 (8)	0.0099 (8)	0.0090 (8)
C23	0.0189 (9)	0.0215 (8)	0.0232 (9)	0.0077 (7)	0.0087 (7)	0.0078 (7)
C24	0.0194 (9)	0.0193 (8)	0.0278 (9)	0.0052 (7)	0.0087 (8)	0.0083 (7)
C25	0.0213 (9)	0.0240 (9)	0.0308 (10)	0.0029 (8)	0.0110 (8)	0.0043 (8)
C26	0.0244 (10)	0.0321 (11)	0.0312 (10)	0.0057 (9)	0.0112 (9)	0.0082 (9)
C27	0.0288 (11)	0.0371 (12)	0.0330 (11)	0.0042 (10)	0.0108 (9)	0.0029 (10)
C28	0.0335 (12)	0.0298 (11)	0.0434 (14)	−0.0027 (10)	0.0131 (11)	−0.0028 (10)
C29	0.0407 (14)	0.0292 (11)	0.0513 (15)	−0.0024 (10)	0.0201 (12)	0.0076 (11)
C30	0.0339 (12)	0.0277 (10)	0.0370 (12)	0.0011 (9)	0.0163 (10)	0.0072 (9)
N9	0.0493 (14)	0.0616 (16)	0.0837 (19)	0.0229 (13)	0.0305 (14)	0.0451 (15)
C33	0.064 (2)	0.104 (3)	0.119 (3)	0.049 (2)	0.062 (2)	0.089 (3)
O3	0.058 (3)	0.091 (6)	0.074 (5)	0.012 (4)	0.048 (4)	0.037 (5)
C31	0.069 (10)	0.143 (13)	0.140 (13)	0.023 (9)	0.065 (9)	0.063 (10)
C32	0.130 (10)	0.151 (13)	0.056 (6)	−0.048 (9)	0.043 (6)	0.001 (7)
O3X	0.038 (2)	0.069 (4)	0.064 (4)	0.006 (2)	0.030 (3)	0.033 (4)
C31X	0.049 (5)	0.063 (4)	0.052 (4)	0.042 (4)	0.037 (4)	0.047 (4)
C32X	0.070 (5)	0.054 (4)	0.048 (5)	0.021 (4)	0.003 (4)	0.004 (4)

Geometric parameters (Å, º) top

Ni1—N2	2.0342 (15)	C14—C15	1.391 (3)
Ni1—N6	2.0373 (15)	C14—H14A	0.9500
Ni1—O1	2.1886 (13)	C15—H15A	0.9500
Ni1—O2	2.2441 (13)	C16—C23	1.475 (3)
Ni1—S1	2.3564 (5)	C17—C18	1.381 (3)
Ni1—S2	2.3866 (5)	C17—C22	1.405 (3)
S1—C9	1.7053 (19)	C18—C19	1.390 (3)
S2—C24	1.728 (2)	C18—H18A	0.9500
O1—C1	1.255 (2)	C19—C20	1.382 (3)
O2—C16	1.248 (2)	C19—H19A	0.9500
N1—C1	1.347 (2)	C20—C21	1.392 (3)
N1—C2	1.414 (2)	C20—H20A	0.9500
N1—H1N1	0.79 (3)	C21—C22	1.388 (3)
N2—C8	1.315 (2)	C21—H21A	0.9500
N2—N3	1.328 (2)	C22—C23	1.451 (3)
N3—C9	1.371 (2)	C25—C26	1.386 (3)
N4—C9	1.352 (2)	C25—C30	1.403 (3)
N4—C10	1.412 (2)	C26—C27	1.385 (3)
N4—H1N4	0.81 (3)	C26—H26A	0.9500
N5—C16	1.352 (3)	C27—C28	1.384 (4)
N5—C17	1.414 (3)	C27—H27A	0.9500
N5—H1N5	0.89 (3)	C28—C29	1.383 (4)
N6—C23	1.302 (2)	C28—H28A	0.9500
N6—N7	1.342 (2)	C29—C30	1.390 (3)
N7—C24	1.335 (2)	C29—H29A	0.9500
N8—C24	1.353 (2)	C30—H30A	0.9500
N8—C25	1.418 (3)	N9—C33	1.347 (4)
N8—H1N8	0.85 (3)	N9—C32X	1.381 (9)
C1—C8	1.464 (2)	N9—C31X	1.408 (10)
C2—C3	1.381 (3)	N9—C31	1.429 (16)
C2—C7	1.410 (2)	N9—C32	1.619 (12)
C3—C4	1.393 (3)	C33—O3X	1.229 (6)
C3—H3A	0.9500	C33—O3	1.298 (8)
C4—C5	1.392 (3)	C33—H33A	0.9500
C4—H4A	0.9500	C33—H33B	0.9600
C5—C6	1.400 (3)	C31—H31A	0.9800
C5—H5A	0.9500	C31—H31B	0.9800
C6—C7	1.389 (3)	C31—H31C	0.9800
C6—H6A	0.9500	C32—H32A	0.9800
C7—C8	1.445 (3)	C32—H32B	0.9800
C10—C15	1.386 (3)	C32—H32C	0.9800
C10—C11	1.396 (3)	C31X—H31D	0.9800
C11—C12	1.386 (3)	C31X—H31E	0.9800
C11—H11A	0.9500	C31X—H31F	0.9800
C12—C13	1.379 (3)	C32X—H32D	0.9800
C12—H12A	0.9500	C32X—H32E	0.9800
C13—C14	1.367 (3)	C32X—H32F	0.9800
C13—H13A	0.9500

N2—Ni1—N6	163.87 (6)	C10—C15—H15A	120.1
N2—Ni1—O1	80.64 (5)	C14—C15—H15A	120.1
N6—Ni1—O1	89.97 (5)	O2—C16—N5	128.61 (19)
N2—Ni1—O2	86.61 (5)	O2—C16—C23	124.53 (17)
N6—Ni1—O2	79.65 (5)	N5—C16—C23	106.86 (17)
O1—Ni1—O2	86.10 (5)	C18—C17—C22	122.1 (2)
N2—Ni1—S1	80.27 (4)	C18—C17—N5	128.4 (2)
N6—Ni1—S1	109.33 (4)	C22—C17—N5	109.45 (18)
O1—Ni1—S1	160.66 (4)	C17—C18—C19	117.1 (2)
O2—Ni1—S1	95.85 (4)	C17—C18—H18A	121.4
N2—Ni1—S2	113.35 (5)	C19—C18—H18A	121.4
N6—Ni1—S2	79.44 (4)	C20—C19—C18	121.4 (2)
O1—Ni1—S2	89.75 (4)	C20—C19—H19A	119.3
O2—Ni1—S2	158.67 (4)	C18—C19—H19A	119.3
S1—Ni1—S2	94.949 (19)	C19—C20—C21	121.3 (2)
C9—S1—Ni1	96.51 (6)	C19—C20—H20A	119.3
C24—S2—Ni1	95.92 (7)	C21—C20—H20A	119.3
C1—O1—Ni1	105.85 (11)	C22—C21—C20	118.1 (2)
C16—O2—Ni1	104.98 (12)	C22—C21—H21A	121.0
C1—N1—C2	110.03 (15)	C20—C21—H21A	121.0
C1—N1—H1N1	125 (2)	C21—C22—C17	119.86 (19)
C2—N1—H1N1	125 (2)	C21—C22—C23	134.39 (19)
C8—N2—N3	119.43 (15)	C17—C22—C23	105.75 (17)
C8—N2—Ni1	113.80 (12)	N6—C23—C22	137.10 (18)
N3—N2—Ni1	126.43 (12)	N6—C23—C16	115.45 (16)
N2—N3—C9	111.47 (15)	C22—C23—C16	107.37 (16)
C9—N4—C10	133.07 (18)	N7—C24—N8	117.60 (17)
C9—N4—H1N4	113.1 (17)	N7—C24—S2	125.57 (15)
C10—N4—H1N4	113.6 (17)	N8—C24—S2	116.77 (15)
C16—N5—C17	110.54 (17)	C26—C25—C30	119.45 (19)
C16—N5—H1N5	124.5 (19)	C26—C25—N8	124.72 (19)
C17—N5—H1N5	124.9 (19)	C30—C25—N8	115.81 (19)
C23—N6—N7	117.97 (16)	C27—C26—C25	120.1 (2)
C23—N6—Ni1	114.66 (12)	C27—C26—H26A	120.0
N7—N6—Ni1	127.13 (12)	C25—C26—H26A	120.0
C24—N7—N6	111.61 (15)	C26—C27—C28	120.8 (2)
C24—N8—C25	130.78 (18)	C26—C27—H27A	119.6
C24—N8—H1N8	112.5 (17)	C28—C27—H27A	119.6
C25—N8—H1N8	116.5 (17)	C29—C28—C27	119.4 (2)
O1—C1—N1	127.81 (17)	C29—C28—H28A	120.3
O1—C1—C8	124.69 (16)	C27—C28—H28A	120.3
N1—C1—C8	107.50 (16)	C28—C29—C30	120.6 (2)
C3—C2—C7	122.46 (17)	C28—C29—H29A	119.7
C3—C2—N1	128.16 (17)	C30—C29—H29A	119.7
C7—C2—N1	109.37 (16)	C29—C30—C25	119.6 (2)
C2—C3—C4	117.01 (18)	C29—C30—H30A	120.2
C2—C3—H3A	121.5	C25—C30—H30A	120.2
C4—C3—H3A	121.5	C33—N9—C32X	111.8 (6)
C5—C4—C3	121.63 (19)	C33—N9—C31X	121.5 (4)
C5—C4—H4A	119.2	C32X—N9—C31X	126.7 (6)
C3—C4—H4A	119.2	C33—N9—C31	119.3 (8)
C4—C5—C6	120.96 (18)	C32X—N9—C31	128.6 (10)
C4—C5—H5A	119.5	C33—N9—C32	132.9 (6)
C6—C5—H5A	119.5	C31X—N9—C32	104.9 (7)
C7—C6—C5	118.11 (17)	C31—N9—C32	107.6 (9)
C7—C6—H6A	120.9	O3X—C33—N9	140.3 (5)
C5—C6—H6A	120.9	O3—C33—N9	107.0 (6)
C6—C7—C2	119.83 (17)	O3X—C33—H33A	89.3
C6—C7—C8	134.55 (17)	O3—C33—H33A	126.5
C2—C7—C8	105.60 (15)	N9—C33—H33A	126.5
N2—C8—C7	137.86 (17)	O3X—C33—H33B	109.8
N2—C8—C1	114.74 (16)	O3—C33—H33B	133.6
C7—C8—C1	107.39 (15)	N9—C33—H33B	109.9
N4—C9—N3	110.48 (16)	N9—C31—H31A	109.5
N4—C9—S1	124.46 (14)	N9—C31—H31B	109.5
N3—C9—S1	125.06 (14)	N9—C31—H31C	109.5
C15—C10—C11	118.47 (18)	N9—C32—H32A	109.5
C15—C10—N4	125.52 (18)	N9—C32—H32B	109.5
C11—C10—N4	115.98 (18)	N9—C32—H32C	109.5
C12—C11—C10	120.7 (2)	N9—C31X—H31D	109.5
C12—C11—H11A	119.6	N9—C31X—H31E	109.5
C10—C11—H11A	119.6	H31D—C31X—H31E	109.5
C13—C12—C11	120.4 (2)	N9—C31X—H31F	109.5
C13—C12—H12A	119.8	H31D—C31X—H31F	109.5
C11—C12—H12A	119.8	H31E—C31X—H31F	109.5
C14—C13—C12	119.0 (2)	N9—C32X—H32D	109.5
C14—C13—H13A	120.5	N9—C32X—H32E	109.5
C12—C13—H13A	120.5	H32D—C32X—H32E	109.5
C13—C14—C15	121.6 (2)	N9—C32X—H32F	109.5
C13—C14—H14A	119.2	H32D—C32X—H32F	109.5
C15—C14—H14A	119.2	H32E—C32X—H32F	109.5
C10—C15—C14	119.8 (2)

N2—Ni1—S1—C9	3.18 (8)	O1—C1—C8—C7	−176.31 (18)
N6—Ni1—S1—C9	−163.42 (8)	N1—C1—C8—C7	3.1 (2)
O1—Ni1—S1—C9	12.56 (14)	C10—N4—C9—N3	−175.2 (2)
O2—Ni1—S1—C9	−82.36 (7)	C10—N4—C9—S1	5.4 (3)
S2—Ni1—S1—C9	116.05 (7)	N2—N3—C9—N4	179.52 (16)
N2—Ni1—S2—C24	−173.88 (8)	N2—N3—C9—S1	−1.1 (2)
N6—Ni1—S2—C24	−4.18 (7)	Ni1—S1—C9—N4	177.06 (16)
O1—Ni1—S2—C24	−94.19 (7)	Ni1—S1—C9—N3	−2.25 (17)
O2—Ni1—S2—C24	−15.62 (13)	C9—N4—C10—C15	11.0 (4)
S1—Ni1—S2—C24	104.59 (6)	C9—N4—C10—C11	−170.9 (2)
N2—Ni1—O1—C1	−2.40 (12)	C15—C10—C11—C12	−0.1 (3)
N6—Ni1—O1—C1	164.43 (13)	N4—C10—C11—C12	−178.4 (2)
O2—Ni1—O1—C1	84.80 (12)	C10—C11—C12—C13	0.4 (4)
S1—Ni1—O1—C1	−11.8 (2)	C11—C12—C13—C14	−0.4 (4)
S2—Ni1—O1—C1	−116.13 (12)	C12—C13—C14—C15	0.1 (4)
N2—Ni1—O2—C16	164.17 (12)	C11—C10—C15—C14	−0.1 (4)
N6—Ni1—O2—C16	−7.35 (12)	N4—C10—C15—C14	178.0 (2)
O1—Ni1—O2—C16	83.33 (12)	C13—C14—C15—C10	0.1 (4)
S1—Ni1—O2—C16	−115.98 (11)	Ni1—O2—C16—N5	−171.38 (18)
S2—Ni1—O2—C16	4.09 (19)	Ni1—O2—C16—C23	8.4 (2)
N6—Ni1—N2—C8	−50.5 (3)	C17—N5—C16—O2	−179.06 (19)
O1—Ni1—N2—C8	4.60 (13)	C17—N5—C16—C23	1.1 (2)
O2—Ni1—N2—C8	−82.01 (13)	C16—N5—C17—C18	179.1 (2)
S1—Ni1—N2—C8	−178.54 (13)	C16—N5—C17—C22	−0.1 (2)
S2—Ni1—N2—C8	90.24 (13)	C22—C17—C18—C19	1.2 (3)
N6—Ni1—N2—N3	122.6 (2)	N5—C17—C18—C19	−177.9 (2)
O1—Ni1—N2—N3	177.76 (16)	C17—C18—C19—C20	−1.0 (3)
O2—Ni1—N2—N3	91.15 (15)	C18—C19—C20—C21	0.2 (4)
S1—Ni1—N2—N3	−5.38 (14)	C19—C20—C21—C22	0.6 (3)
S2—Ni1—N2—N3	−96.60 (14)	C20—C21—C22—C17	−0.5 (3)
C8—N2—N3—C9	178.00 (16)	C20—C21—C22—C23	179.3 (2)
Ni1—N2—N3—C9	5.2 (2)	C18—C17—C22—C21	−0.4 (3)
N2—Ni1—N6—C23	−26.1 (3)	N5—C17—C22—C21	178.82 (18)
O1—Ni1—N6—C23	−80.17 (13)	C18—C17—C22—C23	179.8 (2)
O2—Ni1—N6—C23	5.88 (12)	N5—C17—C22—C23	−1.0 (2)
S1—Ni1—N6—C23	98.50 (13)	N7—N6—C23—C22	−2.1 (3)
S2—Ni1—N6—C23	−169.91 (13)	Ni1—N6—C23—C22	172.66 (19)
N2—Ni1—N6—N7	148.11 (19)	N7—N6—C23—C16	−178.39 (15)
O1—Ni1—N6—N7	94.07 (14)	Ni1—N6—C23—C16	−3.6 (2)
O2—Ni1—N6—N7	−179.88 (15)	C21—C22—C23—N6	5.4 (4)
S1—Ni1—N6—N7	−87.26 (14)	C17—C22—C23—N6	−174.8 (2)
S2—Ni1—N6—N7	4.33 (13)	C21—C22—C23—C16	−178.1 (2)
C23—N6—N7—C24	172.15 (16)	C17—C22—C23—C16	1.6 (2)
Ni1—N6—N7—C24	−1.9 (2)	O2—C16—C23—N6	−4.2 (3)
Ni1—O1—C1—N1	−179.24 (18)	N5—C16—C23—N6	175.61 (16)
Ni1—O1—C1—C8	0.1 (2)	O2—C16—C23—C22	178.46 (18)
C2—N1—C1—O1	176.12 (19)	N5—C16—C23—C22	−1.7 (2)
C2—N1—C1—C8	−3.3 (2)	N6—N7—C24—N8	179.18 (16)
C1—N1—C2—C3	−177.1 (2)	N6—N7—C24—S2	−3.5 (2)
C1—N1—C2—C7	2.3 (2)	C25—N8—C24—N7	4.8 (3)
C7—C2—C3—C4	0.1 (3)	C25—N8—C24—S2	−172.74 (17)
N1—C2—C3—C4	179.3 (2)	Ni1—S2—C24—N7	5.77 (17)
C2—C3—C4—C5	−0.2 (3)	Ni1—S2—C24—N8	−176.93 (14)
C3—C4—C5—C6	−0.3 (3)	C24—N8—C25—C26	−24.4 (3)
C4—C5—C6—C7	0.8 (3)	C24—N8—C25—C30	157.2 (2)
C5—C6—C7—C2	−0.8 (3)	C30—C25—C26—C27	−0.7 (3)
C5—C6—C7—C8	−179.1 (2)	N8—C25—C26—C27	−179.1 (2)
C3—C2—C7—C6	0.4 (3)	C25—C26—C27—C28	0.0 (4)
N1—C2—C7—C6	−178.94 (17)	C26—C27—C28—C29	0.9 (4)
C3—C2—C7—C8	179.16 (18)	C27—C28—C29—C30	−1.1 (4)
N1—C2—C7—C8	−0.2 (2)	C28—C29—C30—C25	0.5 (4)
N3—N2—C8—C7	0.8 (3)	C26—C25—C30—C29	0.5 (3)
Ni1—N2—C8—C7	174.5 (2)	N8—C25—C30—C29	179.0 (2)
N3—N2—C8—C1	−179.47 (16)	C32X—N9—C33—O3X	13.7 (9)
Ni1—N2—C8—C1	−5.8 (2)	C31X—N9—C33—O3X	−165.7 (8)
C6—C7—C8—N2	−3.5 (4)	C31—N9—C33—O3X	−160.5 (10)
C2—C7—C8—N2	178.0 (2)	C32—N9—C33—O3X	26.4 (12)
C6—C7—C8—C1	176.7 (2)	C32X—N9—C33—O3	−16.0 (6)
C2—C7—C8—C1	−1.7 (2)	C31X—N9—C33—O3	164.6 (5)
O1—C1—C8—N2	3.9 (3)	C31—N9—C33—O3	169.7 (9)
N1—C1—C8—N2	−176.67 (16)	C32—N9—C33—O3	−3.3 (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···A	D—H	H···A	D···A	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···O2^iv	0.82 (3)	2.22 (3)	3.006 (3)	161 (2)
C3—H3A···N7ⁱⁱ	0.95	2.56	3.500 (3)	173
C11—H11A···O2^iv	0.95	2.55	3.349 (3)	142
C15—H15A···S1	0.95	2.53	3.194 (3)	127
C20—H20A···S1^v	0.95	2.71	3.443 (2)	135
C26—H26A···N7	0.95	2.35	2.900 (3)	116
C30—H30A···S2ⁱ	0.95	2.84	3.551 (2)	132
C32X—H32D···O3X	0.98	2.46	2.859 (14)	104
C31X—H31E···Cg9^vi	0.98	2.97	3.567 (11)	121
C31X—H31F···Cg7^iv	0.98	2.79	3.460 (10)	126
C32X—H32D···Cg10^vii	0.98	2.91	3.769 (12)	147
C31—H31B···Cg9^vi	0.98	2.98	3.66 (2)	128
C31—H31C···Cg7^iv	0.98	2.78	3.47 (2)	127
C32—H32B···Cg5^iv	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.

Experimental details

Crystal data
Chemical formula	[Ni(C₁₅H₁₁N₄OS)₂]·C₃H₇NO
M_r	722.48
Crystal system, space group	Triclinic, 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)
V (Å³)	1642.31 (5)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.77
Crystal size (mm)	0.45 × 0.15 × 0.13

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.723, 0.906
No. of measured, independent and observed [I > 2σ(I)] reflections	34412, 9435, 7397
R_int	0.033
(sin θ/λ)_max (Å⁻¹)	0.704

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.107, 1.03
No. of reflections	9435
No. of parameters	481
No. of restraints	25
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	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—N2	2.0342 (15)	Ni1—O2	2.2441 (13)
Ni1—N6	2.0373 (15)	Ni1—S1	2.3564 (5)
Ni1—O1	2.1886 (13)	Ni1—S2	2.3866 (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···A	D—H	H···A	D···A	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···O2^iv	0.82 (3)	2.22 (3)	3.006 (3)	161 (2)
C3—H3A···N7ⁱⁱ	0.9500	2.5600	3.500 (3)	173.00
C11—H11A···O2^iv	0.9500	2.5500	3.349 (3)	142.00
C15—H15A···S1	0.9500	2.5300	3.194 (3)	127.00
C20—H20A···S1^v	0.9500	2.7100	3.443 (2)	135.00
C30—H30A···S2ⁱ	0.9500	2.8400	3.551 (2)	132.00
C31X—H31E···Cg9^vi	0.9800	2.97	3.567 (11)	121
C31X—H31F···Cg7^iv	0.9800	2.79	3.460 (10)	126
C32X—H32D···Cg10^vii	0.9800	2.91	3.769 (12)	147
C31—H31B···Cg9^vi	0.9800	2.98	3.66 (2)	128
C31—H31C···Cg7^iv	0.9800	2.78	3.47 (2)	127
C32—H32B···Cg5^iv	0.9800	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.

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

doi:10.1107/S1600536812012834

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