Bis{benzyl 2-[4-(4-meth­oxy­phen­yl)butan-2-yl­idene]hydrazinecarbodithio­ato-κ2N2,S}nickel(II)

Tan, M.-Y.; Ravoof, T.B.S.A.; Tahir, M.I.M.; Crouse, K.A.; Tiekink, E.R.T.

doi:10.1107/S1600536812019289

metal-organic compounds

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ISSN: 2056-9890

Volume 68| Part 6| June 2012| Pages m725-m726

doi:10.1107/S1600536812019289

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Bis{benzyl 2-[4-(4-methoxyphenyl)butan-2-ylidene]hydrazinecarbodithioato-κ²N²,S}nickel(II)

Ming-Yueh Tan,^a Thahira Begum S. A. Ravoof,^a Mohamed Ibrahim Mohamed Tahir,^a Karen A. Crouse ^a ‡ and Edward R. T. Tiekink ^b ^*

^aDepartment of Chemistry, Universiti Putra Malaysia, 43400 Serdang, Malaysia, and ^bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: edward.tiekink@gmail.com

(Received 26 April 2012; accepted 30 April 2012; online 5 May 2012)

The complete molecule of the title complex, [Ni(C₁₉H₂₁N₂OS₂)₂], is generated by the application of twofold symmetry. The Ni^II atom is N,S-chelated by two hydrazinecarbodithioate ligands, which provide an N₂S₂ donor set that defines a distorted square-planar geometry, the S atoms being approximately cis. The conformation of the chelate ring is an envelope with the Ni^II atom being the flap atom. The dihedral angle between the least-squares planes through the chelate rings = 30.10 (6)°. Supramolecular chains propagated by glide symmetry along the c axis and mediated by C—H⋯N contacts feature in the crystal packing.

Related literature

For background to the coordination chemistry of hydrazine carbodithioates, see: Khoo et al. (2005 ); Chan et al. (2008 ); Manan et al. (2012 ). For related syntheses, see Hossain et al. (1996 ).

Experimental

Crystal data

[Ni(C₁₉H₂₁N₂OS₂)₂]
M_r = 773.71
Monoclinic, C 2/c
a = 24.0691 (6) Å
b = 12.5847 (2) Å
c = 12.4179 (3) Å
β = 101.857 (2)°
V = 3681.16 (14) Å³
Z = 4
Mo Kα radiation
μ = 0.79 mm⁻¹
T = 150 K
0.23 × 0.14 × 0.08 mm

Data collection

Agilent Xcalibur Eos Gemini diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011 ) T_min = 0.89, T_max = 0.94
46243 measured reflections
4223 independent reflections
3750 reflections with I > 2σ(I)
R_int = 0.041

Refinement

R[F² > 2σ(F²)] = 0.030
wR(F²) = 0.079
S = 1.01
4223 reflections
224 parameters
H-atom parameters constrained
Δρ_max = 0.80 e Å⁻³
Δρ_min = −0.45 e Å⁻³

Table 1
Selected geometric parameters (Å, °)

Ni—N2	1.9220 (13)
Ni—S1	2.1543 (4)

N2—Ni—S1	85.92 (4)
N2ⁱ—Ni—S1	156.70 (4)
S1ⁱ—Ni—S1	93.66 (2)
N2—Ni—N2ⁱ	103.49 (8)
Symmetry code: (i) $[-x+1, y, -z+{\script{1\over 2}}]$ .

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C10—H10C⋯N1ⁱⁱ	0.98	2.62	3.575 (2)	166
Symmetry code: (ii) -x+1, -y+2, -z+1.

Data collection: CrysAlis PRO (Agilent, 2011); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; 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 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812019289/hg5219sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812019289/hg5219Isup2.hkl

checkCIF report

Comment top

In our on-going investigations to expand the scope of hydrazinecarbodithioate derivatives, their coordination chemistry and bio-activities (Khoo et al., 2005; Chan et al., 2008; Manan et al., 2012), the title complex, (I), was synthesized and characterized crystallographically.

In (I), Fig. 1, the Ni^II atom exists within a distorted square planar cis-N₂S₂ donor set defined by two N,S-chelating hydrazinecarbodithioate ligands, Table 1. The five-membered chelate ring in non-planar (r.m.s. = 0.239 Å) but has an envelope conformation with the Ni atom being the flap atom. A measure of the distortion from the ideal square planar geometry is the dihedral angle of 30.10 (6)° formed between the least-squares planes through the chelate rings. The coordination geometry in (I) resembles that seen in a closely related analogue (Chan et al., 2008).

The hydrazinecarbodithioate ligand is twisted about the N1—N2 bond with the C1—N1—N2—C9 torsion angle being 146.88 (14)°. The dihedral angle between the terminal benzene and phenyl rings is 89.37 (8)°, indicating an almost orthogonal relationship. The methoxy group is co-planar with the benzene ring to which it is connected as seen in the value of the C19—O1—C16—C15 torsion angle of -1.9 (3)°.

The most prominent feature of the crystal packing is the formation of supramolecular chains mediated by C—H···N contacts, Fig. 2 and Table 1. The chains are propagated by glide symmetry along the c axis.

Related literature top

For background to the coordination chemistry of hydrazine carbodithioates, see: Khoo et al. (2005); Chan et al. (2008); Manan et al. (2012). For related syntheses, see Hossain et al. (1996).

Experimental top

4-(4-Methoxyphenyl)butan-2-one (1.70 g, 0.01 mol) in absolute ethanol (20 ml) was added to S-benzyldithiocarbazate (1.98 g, 0.01 mol, prepared as previously described by Hossain et al., 1996) dissolved in hot absolute ethanol (20 ml). The mixture was heated (~340 K) while being stirred for half an hour and then cooled to room temperature. The Schiff base thus formed was filtered and dried in vacuo over anhydrous silica gel. A combination of hot absolute ethanol solutions of the Schiff base (0.36 g, 10 mmol, in 30 ml) and nickel(II) acetate tetrahydrate (0.12 g, 5 mmol, in 10 ml) was stirred at ~340 K for half an hour. The mixture was cooled to room temperature and a green precipitate formed. Dark-green crystals were obtained from its acetonitrile solution after one week. Yield 66%, M.pt: 417 K.

Computing details top

Data collection: CrysAlis PRO (Agilent, 2011); cell refinement: CrysAlis PRO (Agilent, 2011); data reduction: CrysAlis PRO (Agilent, 2011); 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

	Fig. 1. The molecular structure of (I) showing the atom-labelling scheme and displacement ellipsoids at the 50% probability level.
	Fig. 2. A view of the supramolecular chain in (I) mediated by C—H···N interactions, shown as blue dashed lines. Hydrogen atoms not involved in these interactions are omitted.

Bis{benzyl 2-[4-(4-methoxyphenyl)butan-2-ylidene]hydrazinecarbodithioato-κ²N²,S}nickel(II) top

Crystal data top

[Ni(C₁₉H₂₁N₂OS₂)₂]	F(000) = 1624
M_r = 773.71	D_x = 1.396 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 17769 reflections
a = 24.0691 (6) Å	θ = 2.1–28.8°
b = 12.5847 (2) Å	µ = 0.79 mm⁻¹
c = 12.4179 (3) Å	T = 150 K
β = 101.857 (2)°	Block, dark-green
V = 3681.16 (14) Å³	0.23 × 0.14 × 0.08 mm
Z = 4

Data collection top

Agilent Xcalibur Eos Gemini diffractometer	4223 independent reflections
Radiation source: fine-focus sealed tube	3750 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.041
Detector resolution: 16.1952 pixels mm^-1	θ_max = 27.5°, θ_min = 2.4°
ω scans	h = −31→31
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	k = −16→16
T_min = 0.89, T_max = 0.94	l = −16→16
46243 measured reflections

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)] = 0.030	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.079	H-atom parameters constrained
S = 1.01	w = 1/[σ²(F_o²) + (0.0408P)² + 4.0091P] where P = (F_o² + 2F_c²)/3
4223 reflections	(Δ/σ)_max = 0.001
224 parameters	Δρ_max = 0.80 e Å⁻³
0 restraints	Δρ_min = −0.45 e Å⁻³

Crystal data top

[Ni(C₁₉H₂₁N₂OS₂)₂]	V = 3681.16 (14) Å³
M_r = 773.71	Z = 4
Monoclinic, C2/c	Mo Kα radiation
a = 24.0691 (6) Å	µ = 0.79 mm⁻¹
b = 12.5847 (2) Å	T = 150 K
c = 12.4179 (3) Å	0.23 × 0.14 × 0.08 mm
β = 101.857 (2)°

Data collection top

Agilent Xcalibur Eos Gemini diffractometer	4223 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	3750 reflections with I > 2σ(I)
T_min = 0.89, T_max = 0.94	R_int = 0.041
46243 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.030	0 restraints
wR(F²) = 0.079	H-atom parameters constrained
S = 1.01	Δρ_max = 0.80 e Å⁻³
4223 reflections	Δρ_min = −0.45 e Å⁻³
224 parameters

Special details top

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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

	x	y	z	U_iso*/U_eq
Ni	0.5000	0.72365 (2)	0.2500	0.02370 (9)
S1	0.519791 (18)	0.60653 (3)	0.37871 (3)	0.02860 (10)
S2	0.569791 (17)	0.65527 (3)	0.60936 (3)	0.02596 (10)
O1	0.21872 (5)	0.90781 (10)	−0.20500 (10)	0.0370 (3)
N1	0.51555 (6)	0.79888 (10)	0.47242 (10)	0.0241 (3)
N2	0.48562 (6)	0.81821 (10)	0.36271 (10)	0.0241 (3)
C1	0.53185 (6)	0.70112 (12)	0.48301 (12)	0.0230 (3)
C2	0.57260 (7)	0.77439 (12)	0.69281 (13)	0.0270 (3)
H2A	0.5936	0.8310	0.6626	0.032*
H2B	0.5336	0.8002	0.6918	0.032*
C3	0.60211 (7)	0.74882 (13)	0.80923 (12)	0.0253 (3)
C4	0.65150 (7)	0.80300 (13)	0.85687 (14)	0.0295 (3)
H4	0.6669	0.8548	0.8156	0.035*
C5	0.67827 (8)	0.78137 (14)	0.96470 (15)	0.0346 (4)
H5	0.7116	0.8194	0.9973	0.041*
C6	0.65693 (8)	0.70515 (14)	1.02490 (14)	0.0340 (4)
H6	0.6758	0.6900	1.0982	0.041*
C7	0.60778 (8)	0.65067 (14)	0.97798 (14)	0.0322 (4)
H7	0.5928	0.5985	1.0194	0.039*
C8	0.58062 (7)	0.67255 (13)	0.87054 (13)	0.0289 (3)
H8	0.5470	0.6350	0.8386	0.035*
C9	0.44507 (7)	0.88749 (12)	0.35373 (13)	0.0252 (3)
C10	0.42911 (7)	0.94234 (13)	0.44989 (14)	0.0301 (3)
H10A	0.4409	0.8987	0.5160	0.045*
H10B	0.3879	0.9527	0.4356	0.045*
H10C	0.4481	1.0115	0.4610	0.045*
C11	0.40945 (7)	0.91090 (13)	0.24206 (13)	0.0274 (3)
H11A	0.4308	0.8915	0.1848	0.033*
H11B	0.4012	0.9880	0.2357	0.033*
C12	0.35317 (8)	0.84817 (16)	0.22310 (15)	0.0379 (4)
H12A	0.3617	0.7713	0.2322	0.045*
H12B	0.3316	0.8691	0.2795	0.045*
C13	0.31683 (7)	0.86730 (14)	0.10992 (14)	0.0300 (3)
C14	0.27371 (7)	0.94139 (14)	0.09299 (14)	0.0335 (4)
H14	0.2669	0.9818	0.1536	0.040*
C15	0.23988 (7)	0.95834 (13)	−0.01120 (14)	0.0324 (4)
H15	0.2103	1.0097	−0.0214	0.039*
C16	0.24986 (7)	0.89951 (13)	−0.09951 (13)	0.0283 (3)
C17	0.29304 (7)	0.82389 (14)	−0.08368 (14)	0.0301 (3)
H17	0.2998	0.7830	−0.1440	0.036*
C18	0.32596 (7)	0.80872 (14)	0.01994 (14)	0.0321 (4)
H18	0.3555	0.7573	0.0302	0.039*
C19	0.17215 (9)	0.98027 (18)	−0.22191 (17)	0.0487 (5)
H19A	0.1452	0.9589	−0.1766	0.073*
H19B	0.1531	0.9796	−0.2997	0.073*
H19C	0.1861	1.0520	−0.2011	0.073*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ni	0.03115 (16)	0.01813 (14)	0.01918 (14)	0.000	−0.00098 (11)	0.000
S1	0.0414 (2)	0.01877 (18)	0.02279 (19)	0.00211 (15)	−0.00002 (16)	0.00056 (14)
S2	0.0314 (2)	0.02222 (19)	0.02147 (19)	0.00228 (15)	−0.00117 (15)	0.00338 (14)
O1	0.0373 (7)	0.0417 (7)	0.0275 (6)	0.0092 (5)	−0.0035 (5)	0.0002 (5)
N1	0.0269 (7)	0.0232 (6)	0.0191 (6)	0.0003 (5)	−0.0025 (5)	0.0011 (5)
N2	0.0289 (7)	0.0199 (6)	0.0202 (6)	0.0010 (5)	−0.0028 (5)	0.0008 (5)
C1	0.0235 (7)	0.0234 (7)	0.0205 (7)	−0.0023 (6)	0.0005 (6)	0.0019 (6)
C2	0.0317 (8)	0.0234 (7)	0.0236 (8)	0.0004 (6)	0.0003 (6)	0.0011 (6)
C3	0.0270 (8)	0.0256 (7)	0.0221 (7)	0.0032 (6)	0.0022 (6)	−0.0010 (6)
C4	0.0298 (8)	0.0275 (8)	0.0301 (8)	−0.0014 (6)	0.0034 (7)	−0.0002 (6)
C5	0.0324 (9)	0.0339 (9)	0.0325 (9)	0.0014 (7)	−0.0047 (7)	−0.0055 (7)
C6	0.0400 (10)	0.0360 (9)	0.0223 (8)	0.0094 (7)	−0.0020 (7)	−0.0031 (7)
C7	0.0376 (9)	0.0338 (9)	0.0255 (8)	0.0042 (7)	0.0076 (7)	0.0049 (7)
C8	0.0268 (8)	0.0315 (8)	0.0267 (8)	−0.0002 (7)	0.0018 (6)	0.0019 (6)
C9	0.0265 (8)	0.0201 (7)	0.0266 (8)	−0.0025 (6)	−0.0004 (6)	0.0006 (6)
C10	0.0301 (8)	0.0261 (8)	0.0314 (8)	0.0035 (6)	0.0004 (7)	−0.0020 (6)
C11	0.0278 (8)	0.0246 (7)	0.0268 (8)	0.0021 (6)	−0.0011 (6)	0.0041 (6)
C12	0.0351 (9)	0.0445 (10)	0.0298 (9)	−0.0110 (8)	−0.0033 (7)	0.0076 (8)
C13	0.0274 (8)	0.0325 (8)	0.0278 (8)	−0.0073 (7)	0.0001 (6)	0.0031 (7)
C14	0.0359 (9)	0.0332 (9)	0.0300 (8)	−0.0042 (7)	0.0035 (7)	−0.0073 (7)
C15	0.0317 (9)	0.0278 (8)	0.0350 (9)	0.0036 (7)	0.0004 (7)	−0.0032 (7)
C16	0.0269 (8)	0.0293 (8)	0.0261 (8)	−0.0025 (6)	−0.0004 (6)	0.0004 (6)
C17	0.0269 (8)	0.0358 (9)	0.0280 (8)	0.0015 (7)	0.0071 (6)	−0.0021 (7)
C18	0.0231 (8)	0.0357 (9)	0.0363 (9)	0.0021 (7)	0.0033 (7)	0.0034 (7)
C19	0.0449 (11)	0.0524 (12)	0.0401 (11)	0.0189 (9)	−0.0116 (9)	−0.0004 (9)

Geometric parameters (Å, º) top

Ni—N2	1.9220 (13)	C8—H8	0.9500
Ni—N2ⁱ	1.9220 (13)	C9—C11	1.502 (2)
Ni—S1ⁱ	2.1543 (4)	C9—C10	1.496 (2)
Ni—S1	2.1543 (4)	C10—H10A	0.9800
S1—C1	1.7391 (15)	C10—H10B	0.9800
S2—C1	1.7435 (15)	C10—H10C	0.9800
S2—C2	1.8157 (16)	C11—C12	1.544 (2)
O1—C16	1.3731 (19)	C11—H11A	0.9900
O1—C19	1.427 (2)	C11—H11B	0.9900
N1—C1	1.290 (2)	C12—C13	1.514 (2)
N1—N2	1.4250 (17)	C12—H12A	0.9900
N2—C9	1.296 (2)	C12—H12B	0.9900
C2—C3	1.509 (2)	C13—C14	1.379 (2)
C2—H2A	0.9900	C13—C18	1.393 (2)
C2—H2B	0.9900	C14—C15	1.396 (2)
C3—C8	1.390 (2)	C14—H14	0.9500
C3—C4	1.392 (2)	C15—C16	1.384 (2)
C4—C5	1.388 (2)	C15—H15	0.9500
C4—H4	0.9500	C16—C17	1.393 (2)
C5—C6	1.379 (3)	C17—C18	1.379 (2)
C5—H5	0.9500	C17—H17	0.9500
C6—C7	1.388 (3)	C18—H18	0.9500
C6—H6	0.9500	C19—H19A	0.9800
C7—C8	1.387 (2)	C19—H19B	0.9800
C7—H7	0.9500	C19—H19C	0.9800

N2—Ni—S1ⁱ	156.70 (4)	C9—C10—H10A	109.5
N2ⁱ—Ni—S1ⁱ	85.92 (4)	C9—C10—H10B	109.5
N2—Ni—S1	85.92 (4)	H10A—C10—H10B	109.5
N2ⁱ—Ni—S1	156.70 (4)	C9—C10—H10C	109.5
S1ⁱ—Ni—S1	93.66 (2)	H10A—C10—H10C	109.5
N2—Ni—N2ⁱ	103.49 (8)	H10B—C10—H10C	109.5
C1—S1—Ni	93.55 (5)	C9—C11—C12	110.92 (13)
C1—S2—C2	101.05 (7)	C9—C11—H11A	109.5
C16—O1—C19	116.58 (14)	C12—C11—H11A	109.5
C1—N1—N2	110.11 (12)	C9—C11—H11B	109.5
C9—N2—N1	114.89 (13)	C12—C11—H11B	109.5
C9—N2—Ni	126.78 (11)	H11A—C11—H11B	108.0
N1—N2—Ni	117.34 (9)	C13—C12—C11	112.44 (14)
N1—C1—S1	125.18 (12)	C13—C12—H12A	109.1
N1—C1—S2	119.97 (12)	C11—C12—H12A	109.1
S1—C1—S2	114.84 (9)	C13—C12—H12B	109.1
C3—C2—S2	109.02 (11)	C11—C12—H12B	109.1
C3—C2—H2A	109.9	H12A—C12—H12B	107.8
S2—C2—H2A	109.9	C14—C13—C18	118.25 (15)
C3—C2—H2B	109.9	C14—C13—C12	121.48 (16)
S2—C2—H2B	109.9	C18—C13—C12	120.26 (16)
H2A—C2—H2B	108.3	C13—C14—C15	121.46 (16)
C8—C3—C4	119.14 (15)	C13—C14—H14	119.3
C8—C3—C2	121.16 (14)	C15—C14—H14	119.3
C4—C3—C2	119.70 (15)	C16—C15—C14	119.30 (16)
C5—C4—C3	120.01 (16)	C16—C15—H15	120.4
C5—C4—H4	120.0	C14—C15—H15	120.4
C3—C4—H4	120.0	O1—C16—C15	124.44 (15)
C6—C5—C4	120.57 (16)	O1—C16—C17	115.58 (14)
C6—C5—H5	119.7	C15—C16—C17	119.96 (15)
C4—C5—H5	119.7	C18—C17—C16	119.69 (16)
C5—C6—C7	119.78 (16)	C18—C17—H17	120.2
C5—C6—H6	120.1	C16—C17—H17	120.2
C7—C6—H6	120.1	C17—C18—C13	121.34 (16)
C8—C7—C6	119.88 (16)	C17—C18—H18	119.3
C8—C7—H7	120.1	C13—C18—H18	119.3
C6—C7—H7	120.1	O1—C19—H19A	109.5
C7—C8—C3	120.61 (16)	O1—C19—H19B	109.5
C7—C8—H8	119.7	H19A—C19—H19B	109.5
C3—C8—H8	119.7	O1—C19—H19C	109.5
N2—C9—C11	119.22 (14)	H19A—C19—H19C	109.5
N2—C9—C10	123.63 (14)	H19B—C19—H19C	109.5
C11—C9—C10	117.06 (14)

N2—Ni—S1—C1	−20.20 (7)	C6—C7—C8—C3	−0.1 (3)
N2ⁱ—Ni—S1—C1	94.98 (11)	C4—C3—C8—C7	0.2 (2)
S1ⁱ—Ni—S1—C1	−176.85 (6)	C2—C3—C8—C7	−179.21 (15)
C1—N1—N2—C9	146.88 (14)	N1—N2—C9—C11	−177.81 (13)
C1—N1—N2—Ni	−22.50 (16)	Ni—N2—C9—C11	−9.6 (2)
N2ⁱ—Ni—N2—C9	61.33 (12)	N1—N2—C9—C10	−1.3 (2)
S1ⁱ—Ni—N2—C9	−50.50 (19)	Ni—N2—C9—C10	166.88 (12)
S1—Ni—N2—C9	−140.27 (13)	N2—C9—C11—C12	98.22 (18)
N2ⁱ—Ni—N2—N1	−130.72 (12)	C10—C9—C11—C12	−78.50 (18)
S1ⁱ—Ni—N2—N1	117.45 (11)	C9—C11—C12—C13	−178.33 (15)
S1—Ni—N2—N1	27.68 (10)	C11—C12—C13—C14	−96.4 (2)
N2—N1—C1—S1	0.54 (19)	C11—C12—C13—C18	84.4 (2)
N2—N1—C1—S2	179.85 (10)	C18—C13—C14—C15	−0.2 (3)
Ni—S1—C1—N1	16.98 (14)	C12—C13—C14—C15	−179.42 (16)
Ni—S1—C1—S2	−162.36 (8)	C13—C14—C15—C16	0.0 (3)
C2—S2—C1—N1	1.00 (15)	C19—O1—C16—C15	−1.9 (3)
C2—S2—C1—S1	−179.63 (9)	C19—O1—C16—C17	176.42 (17)
C1—S2—C2—C3	177.34 (11)	C14—C15—C16—O1	178.67 (16)
S2—C2—C3—C8	−60.33 (18)	C14—C15—C16—C17	0.4 (3)
S2—C2—C3—C4	120.25 (14)	O1—C16—C17—C18	−178.96 (15)
C8—C3—C4—C5	−0.7 (2)	C15—C16—C17—C18	−0.6 (3)
C2—C3—C4—C5	178.73 (15)	C16—C17—C18—C13	0.3 (3)
C3—C4—C5—C6	1.1 (3)	C14—C13—C18—C17	0.1 (3)
C4—C5—C6—C7	−1.0 (3)	C12—C13—C18—C17	179.30 (16)
C5—C6—C7—C8	0.5 (3)

Symmetry code: (i) −x+1, y, −z+1/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10C···N1ⁱⁱ	0.98	2.62	3.575 (2)	166

Symmetry code: (ii) −x+1, −y+2, −z+1.

Experimental details

Crystal data
Chemical formula	[Ni(C₁₉H₂₁N₂OS₂)₂]
M_r	773.71
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	150
a, b, c (Å)	24.0691 (6), 12.5847 (2), 12.4179 (3)
β (°)	101.857 (2)
V (Å³)	3681.16 (14)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.79
Crystal size (mm)	0.23 × 0.14 × 0.08

Data collection
Diffractometer	Agilent Xcalibur Eos Gemini diffractometer
Absorption correction	Multi-scan (CrysAlis PRO; Agilent, 2011)
T_min, T_max	0.89, 0.94
No. of measured, independent and observed [I > 2σ(I)] reflections	46243, 4223, 3750
R_int	0.041
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.030, 0.079, 1.01
No. of reflections	4223
No. of parameters	224
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.80, −0.45

Computer programs: CrysAlis PRO (Agilent, 2011), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2006), publCIF (Westrip, 2010).

Selected geometric parameters (Å, º) top

Ni—N2	1.9220 (13)	Ni—S1	2.1543 (4)

N2—Ni—S1	85.92 (4)	S1ⁱ—Ni—S1	93.66 (2)
N2ⁱ—Ni—S1	156.70 (4)	N2—Ni—N2ⁱ	103.49 (8)

Symmetry code: (i) −x+1, y, −z+1/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10C···N1ⁱⁱ	0.98	2.62	3.575 (2)	166

Symmetry code: (ii) −x+1, −y+2, −z+1.

Footnotes

‡Additional correspondence author, e-mail: kacrouse@gmail.com.

Acknowledgements

Support for the project came from Universiti Putra Malaysia (UPM) under their Research University Grant Scheme (RUGS Nos 9199834 and 9174000) and from the Malaysian Ministry of Science, Technology and Innovation (grant No. 09–02-04–0752-EA001). MYT wishes to thank UPM for a Graduate Research Fellowship award. We also thank the Ministry of Higher Education (Malaysia) for funding structural studies through the High-Impact Research scheme (UM.C/HIR/MOHE/SC/12).

References

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