Bis[1,5-bis­(1H-indol-3-ylmethyl­ene)thio­carbazonato-κ2N,S]nickel(II) dimethyl sulfoxide disolvate

Rizal, M.R.; Ali, H.M.; Ng, S.W.

doi:10.1107/S1600536808011975

metal-organic compounds

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ISSN: 2056-9890

Volume 64| Part 6| June 2008| Page m755

doi:10.1107/S1600536808011975

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Bis[1,5-bis(1H-indol-3-ylmethylene)thiocarbazonato-κ²N,S]nickel(II) dimethyl sulfoxide disolvate

Mohd. Razali Rizal,^a Hapipah M. Ali ^a and Seik Weng Ng ^a ^*

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

(Received 24 April 2008; accepted 25 April 2008; online 3 May 2008)

The Ni atom in the crystal structure of the centrosymmetric title compound, [Ni(C₁₉H₁₅N₆S)₂]·2C₂H₆OS, is N,S-chelated by the deprotonated Schiff bases in a square-planar geometry. The –CH=N—N=C(S)—NH—N=CH– frament is planar. The two indolyl –NH (donor) sites interact with dimethyl sulfoxide molecules to furnish a layer motif.

Related literature

For the structure of the unsolvated nickel derivative of 1H-indole-3-carboxaldehyde thiosemicarbazone, see: Rizal et al. (2008 ). The ligand is known to be a sensitive complexing agent, see: Ghosh et al. (1999 ).

Experimental

Crystal data

[Ni(C₁₉H₁₅N₆S)₂]·2C₂H₆OS
M_r = 933.83
Monoclinic, C 2/c
a = 19.0340 (5) Å
b = 9.1982 (3) Å
c = 25.1374 (7) Å
β = 95.672 (2)°
V = 4379.5 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.69 mm⁻¹
T = 100 (2) K
0.30 × 0.03 × 0.03 mm

Data collection

Bruker SMART APEX diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.821, T_max = 0.980
27119 measured reflections
5030 independent reflections
3201 reflections with I > 2σ(I)
R_int = 0.092

Refinement

R[F² > 2σ(F²)] = 0.048
wR(F²) = 0.139
S = 1.03
5030 reflections
277 parameters
H-atom parameters constrained
Δρ_max = 0.60 e Å⁻³
Δρ_min = −0.53 e Å⁻³

Table 1
Selected bond lengths (Å)

Ni1—N5	1.906 (3)
Ni1—S1	2.1748 (8)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1n⋯O1	0.88	2.10	2.890 (4)	148
N6—H6n⋯O1ⁱ	0.88	2.03	2.855 (4)	156
Symmetry code: (i) $[-x+{\script{3\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

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: publCIF (Westrip, 2008 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808011975/bt2702sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808011975/bt2702Isup2.hkl

checkCIF report

Comment top

The preceding study reports the nickel derivative of 1H-indole-3-carboxaldehyde thiosemicarbazone (Rizal et al., 2008). With bis(1H-indole-3-carboxaldehyde thiocarbazone) in place of the thiosemicarbazone, the resulting nickel derivative also has the N,S-chelated metal center in a square planar coordination geometry. The compound crystallizes from DMSO as a disolvate (Fig. 1). The oxygen atom of the solvent molecule is a hydrogen bond acceptor to the indolyl amino group of two mononuclear molecules; such a hydrogen bonding scheme gives rise to a layer motif.

Related literature top

For the structure of the unsolvated nickel derivative of 1H-indole-3-carboxaldehyde thiosemicarbazone, see: Rizal et al. (2008). The ligand is known to be a sensitive complexing agent, see: Ghosh et al. (1999).

Experimental top

The Schiff base was synthesized as according to a literature procedure (Ghosh et al., 1999). The Schiff base (2 g, 5.5 mmol) and nickel acetate (0.7 g, 2.8 mmol) were heated in ethanol (50 ml) for 5 h. The brown product was recrystallized from DMSO to give red crystals..

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: publCIF (Westrip, 2008).

Figures top

Fig. 1. Thermal ellipsoid plot (Barbour, 2001) of Ni(C₁₉H₁₅N₆S)₂^.2DMSO at the 70% probability level; hydrogen atoms are drawn as spheres of arbitrary radius. The molecule lies on a center-of-inversion. Unlabeled atoms are related to the labeled ones by this symmetry element.

Bis[1,5-bis(1H-indol-3-ylmethylene)thiocarbazonato- κ²N,S]nickel(II) dimethyl sulfoxide disolvate top

Crystal data top

[Ni(C₁₉H₁₅N₆S)₂]·2C₂H₆OS	F(000) = 1944
M_r = 933.83	D_x = 1.416 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 2255 reflections
a = 19.0340 (5) Å	θ = 2.5–23.1°
b = 9.1982 (3) Å	µ = 0.69 mm⁻¹
c = 25.1374 (7) Å	T = 100 K
β = 95.672 (2)°	Needle, red
V = 4379.5 (2) Å³	0.30 × 0.03 × 0.03 mm
Z = 4

Data collection top

Bruker SMART APEX diffractometer	5030 independent reflections
Radiation source: fine-focus sealed tube	3201 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.092
ϕ and ω scans	θ_max = 27.5°, θ_min = 1.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −24→24
T_min = 0.821, T_max = 0.980	k = −11→9
27119 measured reflections	l = −32→32

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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.139	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0695P)²] where P = (F_o² + 2F_c²)/3
5030 reflections	(Δ/σ)_max = 0.001
277 parameters	Δρ_max = 0.60 e Å⁻³
0 restraints	Δρ_min = −0.53 e Å⁻³

Crystal data top

[Ni(C₁₉H₁₅N₆S)₂]·2C₂H₆OS	V = 4379.5 (2) Å³
M_r = 933.83	Z = 4
Monoclinic, C2/c	Mo Kα radiation
a = 19.0340 (5) Å	µ = 0.69 mm⁻¹
b = 9.1982 (3) Å	T = 100 K
c = 25.1374 (7) Å	0.30 × 0.03 × 0.03 mm
β = 95.672 (2)°

Data collection top

Bruker SMART APEX diffractometer	5030 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3201 reflections with I > 2σ(I)
T_min = 0.821, T_max = 0.980	R_int = 0.092
27119 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.048	0 restraints
wR(F²) = 0.139	H-atom parameters constrained
S = 1.04	Δρ_max = 0.60 e Å⁻³
5030 reflections	Δρ_min = −0.53 e Å⁻³
277 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.

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

	x	y	z	U_iso*/U_eq
Ni1	0.7500	0.7500	0.5000	0.02112 (17)
S1	0.71406 (4)	0.69712 (10)	0.41745 (3)	0.0248 (2)
S2	0.54373 (5)	0.32873 (12)	0.03925 (4)	0.0426 (3)
N1	0.67553 (16)	0.4672 (4)	0.14187 (11)	0.0407 (8)
H1N	0.6749	0.4384	0.1084	0.049*
N2	0.73446 (14)	0.5251 (3)	0.32226 (10)	0.0275 (6)
N3	0.77036 (14)	0.4729 (3)	0.36844 (10)	0.0278 (6)
H3N	0.7967	0.3945	0.3674	0.033*
N4	0.80017 (13)	0.4836 (3)	0.45745 (9)	0.0228 (6)
N5	0.79004 (13)	0.5599 (3)	0.50425 (9)	0.0219 (6)
N6	0.87026 (13)	0.1142 (3)	0.54254 (10)	0.0256 (6)
H6N	0.8770	0.0305	0.5269	0.031*
O1	0.61523 (12)	0.3930 (3)	0.03531 (9)	0.0361 (6)
C1	0.71111 (19)	0.3994 (5)	0.18458 (13)	0.0366 (9)
H1	0.7380	0.3128	0.1830	0.044*
C2	0.64128 (19)	0.5856 (4)	0.15846 (13)	0.0347 (9)
C3	0.59816 (19)	0.6863 (5)	0.13031 (15)	0.0410 (10)
H3	0.5891	0.6801	0.0925	0.049*
C4	0.5688 (2)	0.7948 (5)	0.15795 (16)	0.0437 (10)
H4	0.5390	0.8642	0.1390	0.052*
C5	0.5817 (2)	0.8061 (5)	0.21364 (16)	0.0445 (10)
H5	0.5606	0.8827	0.2318	0.053*
C6	0.62496 (18)	0.7069 (4)	0.24255 (14)	0.0344 (9)
H6	0.6332	0.7142	0.2804	0.041*
C7	0.65623 (18)	0.5962 (4)	0.21512 (12)	0.0314 (8)
C8	0.70192 (18)	0.4760 (4)	0.23012 (12)	0.0321 (8)
C9	0.73595 (18)	0.4385 (4)	0.28191 (12)	0.0307 (8)
H9	0.7600	0.3482	0.2866	0.037*
C10	0.76516 (16)	0.5425 (4)	0.41603 (12)	0.0237 (7)
C11	0.80984 (15)	0.4880 (4)	0.54786 (12)	0.0239 (7)
H11	0.8051	0.5388	0.5802	0.029*
C12	0.83747 (16)	0.3449 (4)	0.55418 (12)	0.0237 (7)
C13	0.84099 (16)	0.2324 (4)	0.51784 (12)	0.0235 (7)
H13	0.8250	0.2380	0.4809	0.028*
C14	0.88816 (16)	0.1434 (4)	0.59618 (13)	0.0274 (8)
C15	0.92233 (17)	0.0566 (4)	0.63616 (13)	0.0346 (9)
H15	0.9361	−0.0403	0.6293	0.042*
C16	0.93510 (19)	0.1182 (5)	0.68610 (14)	0.0410 (10)
H16	0.9589	0.0626	0.7142	0.049*
C17	0.91418 (19)	0.2594 (5)	0.69662 (14)	0.0400 (9)
H17	0.9234	0.2975	0.7317	0.048*
C18	0.88050 (17)	0.3447 (4)	0.65717 (12)	0.0330 (9)
H18	0.8661	0.4408	0.6647	0.040*
C19	0.86766 (16)	0.2867 (4)	0.60527 (13)	0.0252 (7)
C20	0.5318 (2)	0.1994 (5)	−0.01409 (19)	0.0615 (13)
H20A	0.5247	0.2508	−0.0483	0.092*
H20B	0.4904	0.1390	−0.0096	0.092*
H20C	0.5737	0.1374	−0.0136	0.092*
C21	0.5542 (2)	0.2019 (5)	0.09367 (19)	0.0580 (13)
H21A	0.5617	0.2551	0.1275	0.087*
H21B	0.5950	0.1393	0.0897	0.087*
H21C	0.5116	0.1420	0.0935	0.087*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ni1	0.0294 (3)	0.0185 (3)	0.0161 (3)	−0.0020 (3)	0.0053 (2)	−0.0006 (2)
S1	0.0359 (4)	0.0216 (5)	0.0173 (4)	−0.0002 (4)	0.0042 (3)	−0.0015 (3)
S2	0.0332 (5)	0.0450 (7)	0.0512 (6)	0.0053 (5)	0.0129 (4)	0.0132 (5)
N1	0.053 (2)	0.048 (2)	0.0219 (15)	0.0008 (17)	0.0073 (14)	−0.0063 (14)
N2	0.0343 (15)	0.0295 (18)	0.0192 (13)	−0.0021 (13)	0.0053 (11)	−0.0032 (12)
N3	0.0378 (16)	0.0256 (17)	0.0202 (13)	0.0056 (13)	0.0041 (11)	−0.0039 (12)
N4	0.0314 (14)	0.0211 (16)	0.0166 (12)	−0.0005 (12)	0.0059 (11)	−0.0036 (11)
N5	0.0259 (14)	0.0213 (16)	0.0192 (12)	−0.0018 (12)	0.0069 (10)	−0.0026 (11)
N6	0.0275 (14)	0.0239 (17)	0.0255 (14)	0.0023 (12)	0.0028 (11)	−0.0027 (12)
O1	0.0355 (13)	0.0473 (18)	0.0255 (12)	−0.0032 (12)	0.0031 (10)	0.0014 (11)
C1	0.049 (2)	0.039 (2)	0.0228 (17)	0.0024 (18)	0.0068 (16)	−0.0055 (16)
C2	0.039 (2)	0.039 (3)	0.0268 (18)	−0.0054 (18)	0.0087 (15)	0.0032 (17)
C3	0.043 (2)	0.049 (3)	0.0314 (19)	−0.002 (2)	0.0063 (17)	0.0078 (18)
C4	0.040 (2)	0.043 (3)	0.047 (2)	−0.0003 (19)	−0.0002 (18)	0.012 (2)
C5	0.040 (2)	0.042 (3)	0.054 (2)	0.0023 (19)	0.0148 (19)	0.004 (2)
C6	0.0386 (19)	0.036 (2)	0.0304 (18)	−0.0014 (17)	0.0104 (15)	0.0004 (16)
C7	0.0352 (19)	0.037 (2)	0.0235 (16)	−0.0067 (17)	0.0086 (14)	0.0000 (15)
C8	0.040 (2)	0.035 (2)	0.0218 (16)	0.0003 (17)	0.0072 (15)	−0.0051 (15)
C9	0.0378 (19)	0.030 (2)	0.0249 (17)	0.0000 (16)	0.0079 (14)	−0.0034 (15)
C10	0.0269 (16)	0.024 (2)	0.0214 (15)	−0.0052 (14)	0.0077 (13)	−0.0041 (14)
C11	0.0260 (16)	0.025 (2)	0.0210 (15)	−0.0025 (14)	0.0059 (13)	−0.0033 (14)
C12	0.0243 (16)	0.025 (2)	0.0221 (15)	−0.0018 (14)	0.0040 (12)	−0.0026 (14)
C13	0.0241 (15)	0.022 (2)	0.0241 (16)	0.0008 (14)	0.0030 (12)	0.0015 (14)
C14	0.0211 (16)	0.033 (2)	0.0285 (17)	−0.0031 (14)	0.0039 (13)	0.0019 (15)
C15	0.0316 (19)	0.034 (2)	0.0370 (19)	−0.0002 (16)	−0.0006 (15)	0.0077 (17)
C16	0.035 (2)	0.050 (3)	0.036 (2)	−0.0012 (19)	−0.0063 (16)	0.0151 (19)
C17	0.043 (2)	0.050 (3)	0.0260 (18)	−0.006 (2)	−0.0013 (15)	0.0019 (18)
C18	0.0357 (19)	0.039 (2)	0.0247 (17)	−0.0036 (17)	0.0024 (15)	−0.0016 (16)
C19	0.0243 (16)	0.024 (2)	0.0280 (17)	−0.0036 (13)	0.0051 (13)	0.0024 (14)
C20	0.042 (2)	0.064 (3)	0.077 (3)	−0.018 (2)	−0.005 (2)	−0.012 (3)
C21	0.049 (2)	0.053 (3)	0.076 (3)	0.010 (2)	0.026 (2)	0.031 (2)

Geometric parameters (Å, º) top

Ni1—N5ⁱ	1.906 (3)	C5—C6	1.386 (5)
Ni1—N5	1.906 (3)	C5—H5	0.9500
Ni1—S1ⁱ	2.1748 (8)	C6—C7	1.396 (5)
Ni1—S1	2.1748 (8)	C6—H6	0.9500
S1—C10	1.726 (3)	C7—C8	1.434 (5)
S2—O1	1.496 (2)	C8—C9	1.438 (5)
S2—C20	1.790 (5)	C9—H9	0.9500
S2—C21	1.794 (4)	C11—C12	1.420 (5)
N1—C2	1.356 (5)	C11—H11	0.9500
N1—C1	1.362 (4)	C12—C13	1.386 (4)
N1—H1N	0.8800	C12—C19	1.456 (4)
N2—C9	1.293 (4)	C13—H13	0.9500
N2—N3	1.374 (4)	C14—C15	1.394 (5)
N3—C10	1.369 (4)	C14—C19	1.400 (5)
N3—H3N	0.8800	C15—C16	1.377 (5)
N4—C10	1.298 (4)	C15—H15	0.9500
N4—N5	1.400 (3)	C16—C17	1.392 (6)
N5—C11	1.304 (4)	C16—H16	0.9500
N6—C13	1.345 (4)	C17—C18	1.372 (5)
N6—C14	1.384 (4)	C17—H17	0.9500
N6—H6N	0.8800	C18—C19	1.408 (4)
C1—C8	1.370 (5)	C18—H18	0.9500
C1—H1	0.9500	C20—H20A	0.9800
C2—C3	1.385 (5)	C20—H20B	0.9800
C2—C7	1.428 (4)	C20—H20C	0.9800
C3—C4	1.367 (6)	C21—H21A	0.9800
C3—H3	0.9500	C21—H21B	0.9800
C4—C5	1.401 (5)	C21—H21C	0.9800
C4—H4	0.9500

N5ⁱ—Ni1—N5	180.000 (1)	C7—C8—C9	129.1 (3)
N5ⁱ—Ni1—S1ⁱ	86.25 (7)	N2—C9—C8	121.3 (3)
N5—Ni1—S1ⁱ	93.75 (7)	N2—C9—H9	119.3
N5ⁱ—Ni1—S1	93.75 (7)	C8—C9—H9	119.3
N5—Ni1—S1	86.25 (7)	N4—C10—N3	115.5 (3)
S1ⁱ—Ni1—S1	180.000 (1)	N4—C10—S1	125.0 (2)
C10—S1—Ni1	94.55 (10)	N3—C10—S1	119.5 (2)
O1—S2—C20	105.20 (18)	N5—C11—C12	129.6 (3)
O1—S2—C21	105.92 (18)	N5—C11—H11	115.2
C20—S2—C21	97.8 (3)	C12—C11—H11	115.2
C2—N1—C1	110.0 (3)	C13—C12—C11	131.2 (3)
C2—N1—H1N	125.0	C13—C12—C19	105.5 (3)
C1—N1—H1N	125.0	C11—C12—C19	123.3 (3)
C9—N2—N3	113.5 (3)	N6—C13—C12	110.1 (3)
C10—N3—N2	120.1 (3)	N6—C13—H13	124.9
C10—N3—H3N	119.9	C12—C13—H13	124.9
N2—N3—H3N	119.9	N6—C14—C15	130.1 (3)
C10—N4—N5	111.3 (3)	N6—C14—C19	107.2 (3)
C11—N5—N4	113.6 (3)	C15—C14—C19	122.7 (3)
C11—N5—Ni1	126.4 (2)	C16—C15—C14	116.7 (4)
N4—N5—Ni1	120.03 (19)	C16—C15—H15	121.6
C13—N6—C14	110.1 (3)	C14—C15—H15	121.6
C13—N6—H6N	125.0	C15—C16—C17	122.0 (3)
C14—N6—H6N	125.0	C15—C16—H16	119.0
N1—C1—C8	109.2 (4)	C17—C16—H16	119.0
N1—C1—H1	125.4	C18—C17—C16	121.2 (3)
C8—C1—H1	125.4	C18—C17—H17	119.4
N1—C2—C3	131.2 (3)	C16—C17—H17	119.4
N1—C2—C7	107.9 (3)	C17—C18—C19	118.6 (4)
C3—C2—C7	120.9 (4)	C17—C18—H18	120.7
C4—C3—C2	118.7 (4)	C19—C18—H18	120.7
C4—C3—H3	120.7	C14—C19—C18	118.8 (3)
C2—C3—H3	120.7	C14—C19—C12	107.1 (3)
C3—C4—C5	121.5 (4)	C18—C19—C12	134.1 (3)
C3—C4—H4	119.3	S2—C20—H20A	109.5
C5—C4—H4	119.3	S2—C20—H20B	109.5
C6—C5—C4	120.8 (4)	H20A—C20—H20B	109.5
C6—C5—H5	119.6	S2—C20—H20C	109.5
C4—C5—H5	119.6	H20A—C20—H20C	109.5
C5—C6—C7	118.8 (3)	H20B—C20—H20C	109.5
C5—C6—H6	120.6	S2—C21—H21A	109.5
C7—C6—H6	120.6	S2—C21—H21B	109.5
C6—C7—C2	119.3 (3)	H21A—C21—H21B	109.5
C6—C7—C8	135.2 (3)	S2—C21—H21C	109.5
C2—C7—C8	105.4 (3)	H21A—C21—H21C	109.5
C1—C8—C7	107.5 (3)	H21B—C21—H21C	109.5
C1—C8—C9	123.4 (4)

N5ⁱ—Ni1—S1—C10	167.97 (12)	C7—C8—C9—N2	−8.1 (6)
N5—Ni1—S1—C10	−12.03 (12)	N5—N4—C10—N3	−178.4 (2)
C9—N2—N3—C10	−170.8 (3)	N5—N4—C10—S1	1.3 (4)
C10—N4—N5—C11	164.8 (3)	N2—N3—C10—N4	179.0 (3)
C10—N4—N5—Ni1	−14.8 (3)	N2—N3—C10—S1	−0.7 (4)
S1ⁱ—Ni1—N5—C11	17.7 (3)	Ni1—S1—C10—N4	9.5 (3)
S1—Ni1—N5—C11	−162.3 (3)	Ni1—S1—C10—N3	−170.8 (2)
S1ⁱ—Ni1—N5—N4	−162.8 (2)	N4—N5—C11—C12	−2.2 (5)
S1—Ni1—N5—N4	17.2 (2)	Ni1—N5—C11—C12	177.4 (2)
C2—N1—C1—C8	−1.6 (4)	N5—C11—C12—C13	−12.0 (6)
C1—N1—C2—C3	−179.1 (4)	N5—C11—C12—C19	170.0 (3)
C1—N1—C2—C7	0.7 (4)	C14—N6—C13—C12	−0.7 (4)
N1—C2—C3—C4	178.5 (4)	C11—C12—C13—N6	−178.3 (3)
C7—C2—C3—C4	−1.3 (6)	C19—C12—C13—N6	0.0 (4)
C2—C3—C4—C5	0.3 (6)	C13—N6—C14—C15	−176.7 (3)
C3—C4—C5—C6	0.0 (6)	C13—N6—C14—C19	1.1 (3)
C4—C5—C6—C7	0.7 (6)	N6—C14—C15—C16	177.8 (3)
C5—C6—C7—C2	−1.8 (5)	C19—C14—C15—C16	0.4 (5)
C5—C6—C7—C8	−179.1 (4)	C14—C15—C16—C17	0.9 (5)
N1—C2—C7—C6	−177.7 (3)	C15—C16—C17—C18	−0.9 (6)
C3—C2—C7—C6	2.1 (5)	C16—C17—C18—C19	−0.4 (5)
N1—C2—C7—C8	0.3 (4)	N6—C14—C19—C18	−179.5 (3)
C3—C2—C7—C8	−179.8 (3)	C15—C14—C19—C18	−1.6 (5)
N1—C1—C8—C7	1.8 (4)	N6—C14—C19—C12	−1.1 (3)
N1—C1—C8—C9	−176.2 (3)	C15—C14—C19—C12	176.9 (3)
C6—C7—C8—C1	176.3 (4)	C17—C18—C19—C14	1.5 (5)
C2—C7—C8—C1	−1.3 (4)	C17—C18—C19—C12	−176.4 (3)
C6—C7—C8—C9	−5.9 (7)	C13—C12—C19—C14	0.7 (3)
C2—C7—C8—C9	176.5 (3)	C11—C12—C19—C14	179.1 (3)
N3—N2—C9—C8	−179.2 (3)	C13—C12—C19—C18	178.8 (3)
C1—C8—C9—N2	169.4 (3)	C11—C12—C19—C18	−2.7 (6)

Symmetry code: (i) −x+3/2, −y+3/2, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1n···O1	0.88	2.10	2.890 (4)	148
N6—H6n···O1ⁱⁱ	0.88	2.03	2.855 (4)	156

Symmetry code: (ii) −x+3/2, y−1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	[Ni(C₁₉H₁₅N₆S)₂]·2C₂H₆OS
M_r	933.83
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	100
a, b, c (Å)	19.0340 (5), 9.1982 (3), 25.1374 (7)
β (°)	95.672 (2)
V (Å³)	4379.5 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.69
Crystal size (mm)	0.30 × 0.03 × 0.03

Data collection
Diffractometer	Bruker SMART APEX diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.821, 0.980
No. of measured, independent and observed [I > 2σ(I)] reflections	27119, 5030, 3201
R_int	0.092
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.048, 0.139, 1.04
No. of reflections	5030
No. of parameters	277
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.60, −0.53

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

Selected bond lengths (Å) top

Ni1—N5

1.906 (3)

Ni1—S1

2.1748 (8)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1n···O1	0.88	2.10	2.890 (4)	148
N6—H6n···O1ⁱ	0.88	2.03	2.855 (4)	156

Symmetry code: (i) −x+3/2, y−1/2, −z+1/2.

Acknowledgements

We thank the Science Fund (12–02-03–2031) for supporting this study, and the University of Malaya for the purchase of the diffractometer.

References

Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191. CrossRef CAS Google Scholar
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Rizal, M. R., Ali, H. M. & Ng, S. W. (2008). Acta Cryst. E64. submitted (sg2241). Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Westrip, S. P. (2008). publCIF. In preparation. Google Scholar

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