Crystal structure of bis­[S-hexyl 3-(4-methyl­benzyl­idene)di­thio­carbazato-κ2N3,S]nickel(II)

Howlader, M.B.H.; Begum, M.S.; Sheikh, M.C.; Miyatake, R.; Zangrando, E.

doi:10.1107/S2056989015000328

metal-organic compounds

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ISSN: 2056-9890

Volume 71| Part 2| February 2015| Pages m26-m27

doi:10.1107/S2056989015000328

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Crystal structure of bis[S-hexyl 3-(4-methylbenzylidene)dithiocarbazato-κ²N³,S]nickel(II)

M. B. H. Howlader,^a M. S. Begum,^a ^* M. C. Sheikh,^b R. Miyatake ^c and E. Zangrando ^d

^aDepartment of Chemistry, Rajshahi University, Rajshahi-6205, Bangladesh, ^bDepartment of Applied Chemistry, Faculty of Engineering, University of Toyama, 3190 Gofuku, Toyama 930-8555, Japan, ^cCenter for Environmental Conservation and Research Safety, University of Toyama, 3190 Gofuku, Toyama 930-8555, Japan, and ^dDepartment of Chemical and Pharmaceutical Sciences, via Giorgieri 1, 34127 Trieste, Italy
^*Correspondence e-mail: sabina_sust@yahoo.com

Edited by P. Dastidar, Indian Association for the Cultivation of Science, India (Received 2 January 2015; accepted 7 January 2015; online 14 January 2015)

In the title complex, [Ni(C₁₅H₂₁N₂S₂)₂], the Ni^II atom exhibits a square-planar coordination geometry and is located on an inversion centre leading to a trans configuration of the N,S-chelating ligands. In the crystal, the complex molecules stack at a distance of 4.6738 (3) Å along the a axis, which exclude any significant interactions between the aromatic rings.

Keywords: crystal structure; nickel complex; dithiocarbazate.

CCDC reference: 1035820

1. Related literature

For the structures of related complexes, see: Chan et al. (2008 ); Islam et al. (2011 , 2014 ); Li et al. (2006 ); Zhang et al. (2004 ). For the structure of the ligand, see: Howlader et al. (2015 ).

2. Experimental

2.1. Crystal data

[Ni(C₁₅H₂₁N₂S₂)₂]
M_r = 645.62
Triclinic, $[P \overline 1]$
a = 4.6738 (3) Å
b = 10.5132 (5) Å
c = 16.4789 (8) Å
α = 86.522 (3)°
β = 84.850 (3)°
γ = 79.057 (3)°
V = 791.00 (7) Å³
Z = 1
Cu Kα radiation
μ = 3.55 mm⁻¹
T = 173 K
0.37 × 0.08 × 0.02 mm

2.2. Data collection

Rigaku R-AXIS RAPID diffractometer
Absorption correction: multi-scan (ABSCOR; Rigaku, 1995 ) T_min = 0.615, T_max = 0.932
9100 measured reflections
2834 independent reflections
2029 reflections with F² > 2σ(F²)
R_int = 0.074

2.3. Refinement

R[F² > 2σ(F²)] = 0.071
wR(F²) = 0.218
S = 1.09
2834 reflections
180 parameters
H-atom parameters constrained
Δρ_max = 0.98 e Å⁻³
Δρ_min = −0.35 e Å⁻³

Table 1
Selected bond lengths (Å)

Ni—N1	1.933 (3)
Ni—S1	2.1775 (10)

Data collection: RAPID-AUTO (Rigaku, 2001 ); cell refinement: RAPID-AUTO; data reduction: RAPID-AUTO; program(s) used to solve structure: SIR92 (Altomare et al., 1994 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ); molecular graphics: CrystalStructure (Rigaku, 2010 ); software used to prepare material for publication: CrystalStructure.

Supporting information

CCDC reference: 1035820

Crystal structure: contains datablocks General, I. DOI: 10.1107/S2056989015000328/ds2244sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S2056989015000328/ds2244Isup2.hkl

checkCIF report

Structural commentary top

The metal is located on a crystallographic inversion centre and the two Schiff bases, in their deprotonated imino thiolate form, act as chelating ligands to the metal centre via the azomethine nitrogen N1 and thiolate sulphur S1 atoms in a trans-planar configuration as imposed by the crystal symmetry. The complex has coplanar geometry with the exception of the hexyl chains that pend hedgewise. In the complex, the Ni—S and Ni–N bond distances are of 2.1777 (11) and 1.933 (4) Å, respectively, with a S(2)—Ni—N(2) chelating angle of 86.06 (10)°. These geometrical parameters agree with those reported for similar nickel complexes either when ligands assume a trans (Islam, et al., 2011; Islam, et al., 2014; Zhang, et al., 2004) or a cis configuration (Chan, et al., 2008; Li, et al., 2006). The ligand, recently reported (Howlader, et al., 2015), underwent rotation about the C9—N2 by 180° in order to allow the N,S chelating behavior towards the metal. Upon coordination some salient features are observed with respect to the free ligand, and the most significant are an elongation of the C(9)—S(1) bond length (1.720 (4) Å in NiL₂ that must be compared to 1.670 (3) Å in HL, thus validating the coordination with deprotonated thiolate sulphur atom. Correspondingly the N(2)—C(9) bond length, of 1.335 (3) Å, shortens to 1.270 (6) Å in the NiL₂ complex, while the N(1)—N(2) bond length of 1.375 (3) Å in HL is slightly elongated in the complex (1.426 (5) Å, Table 1).

Supramolecular features top

The complexes stack at a distance of 4.6738 (3) Å (axis a), which exclude any significant interactions between the aromatic rings.

Synthesis and crystallization top

A solution of Ni(CH₃COO)₂.4H₂O (0.06 g, 0.25 mmol, 8 mL methanol) was added to a solution of the ligand, S-hexyl (E)-3-(4-methylbenzylidene)dithiocarbazate, (0.15 g, 0.5 mmol, 10 mL methanol ). The resulting mixture was stirred at room temperature for four hours. A dark reddish brown precipitate was formed, filtered off, washed with methanol and dried in vacuo over anhydrous CaCl₂. Dark reddish brown single crystals, suitable for X-ray diffraction, of the compound were obtained by slow evaporation from a mixture of chloroform and acetonitrile (1:1) after 7 days. M.P. 374 K.

Refinement top

Crystal data, data collection and structure refinement details are summarized in Table 1. All H atoms were located geometrically and treated as riding atoms, with C—H = 0.95–0.99 Å, and with Uĩso~(H) = 1.2U~eq~(C) or 1.5U~eq~(C) for methyl H atoms.

Related literature top

For the structures of related complexes, see: Chan et al. (2008); Islam et al. (2011, 2014); Li et al. (2006); Zhang et al. (2004). For the ligand, see: Howlader et al. (2015).

Computing details top

Data collection: RAPID-AUTO (Rigaku, 2001); cell refinement: RAPID-AUTO (Rigaku, 2001); data reduction: RAPID-AUTO (Rigaku, 2001); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: CrystalStructure (Rigaku, 2010); software used to prepare material for publication: CrystalStructure (Rigaku, 2010).

Figures top

	Fig. 1. ORTEP drawing (ellipsoid probability at 50%) of the centrosymmetric NiL₂ complex.
	Fig. 2. Crystal packing of the complex.

Bis[S-hexyl 3-(4-methylbenzylidene)dithiocarbazato-κ²N³,S]nickel(II) top

Crystal data top

[Ni(C₁₅H₂₁N₂S₂)₂]	Z = 1
M_r = 645.62	F(000) = 342.00
Triclinic, P1	D_x = 1.355 Mg m⁻³
Hall symbol: -P 1	Cu Kα radiation, λ = 1.54187 Å
a = 4.6738 (3) Å	Cell parameters from 5923 reflections
b = 10.5132 (5) Å	θ = 4.3–68.2°
c = 16.4789 (8) Å	µ = 3.55 mm⁻¹
α = 86.522 (3)°	T = 173 K
β = 84.850 (3)°	Platelet, brown
γ = 79.057 (3)°	0.37 × 0.08 × 0.02 mm
V = 791.00 (7) Å³

Data collection top

Rigaku R-AXIS RAPID diffractometer	2029 reflections with F² > 2σ(F²)
Detector resolution: 10.000 pixels mm^-1	R_int = 0.074
ω scans	θ_max = 68.2°
Absorption correction: multi-scan (ABSCOR; Rigaku, 1995)	h = −5→5
T_min = 0.615, T_max = 0.932	k = −12→12
9100 measured reflections	l = −19→19
2834 independent reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.071	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.218	H-atom parameters constrained
S = 1.09	w = 1/[σ²(F_o²) + (0.1314P)²] where P = (F_o² + 2F_c²)/3
2834 reflections	(Δ/σ)_max < 0.001
180 parameters	Δρ_max = 0.98 e Å⁻³
0 restraints	Δρ_min = −0.35 e Å⁻³
Primary atom site location: structure-invariant direct methods

Crystal data top

[Ni(C₁₅H₂₁N₂S₂)₂]	γ = 79.057 (3)°
M_r = 645.62	V = 791.00 (7) Å³
Triclinic, P1	Z = 1
a = 4.6738 (3) Å	Cu Kα radiation
b = 10.5132 (5) Å	µ = 3.55 mm⁻¹
c = 16.4789 (8) Å	T = 173 K
α = 86.522 (3)°	0.37 × 0.08 × 0.02 mm
β = 84.850 (3)°

Data collection top

Rigaku R-AXIS RAPID diffractometer	2834 independent reflections
Absorption correction: multi-scan (ABSCOR; Rigaku, 1995)	2029 reflections with F² > 2σ(F²)
T_min = 0.615, T_max = 0.932	R_int = 0.074
9100 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.071	0 restraints
wR(F²) = 0.218	H-atom parameters constrained
S = 1.09	Δρ_max = 0.98 e Å⁻³
2834 reflections	Δρ_min = −0.35 e Å⁻³
180 parameters

Special details top

Refinement. Refinement was performed using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F². R-factor (gt) are based on F. The threshold expression of F² > 2.0 σ(F²) is used only for calculating R-factor (gt).

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

	x	y	z	U_iso*/U_eq
Ni	1.0000	1.0000	1.0000	0.0372 (4)
S1	1.1112 (3)	0.83443 (10)	0.92242 (6)	0.0516 (4)
S2	1.4585 (2)	0.80909 (9)	0.76635 (6)	0.0479 (4)
N1	0.7454 (7)	0.9180 (3)	1.07644 (18)	0.0365 (8)
N2	1.3765 (7)	1.0201 (3)	0.85050 (18)	0.0405 (8)
C1	−0.0675 (10)	0.4837 (4)	1.2473 (3)	0.0514 (11)
H1A	−0.0056	0.4630	1.3025	0.077*
H1B	−0.0491	0.4035	1.2184	0.077*
H1C	−0.2717	0.5288	1.2503	0.077*
C2	0.1222 (9)	0.5695 (4)	1.2022 (2)	0.0420 (10)
C3	0.1476 (9)	0.6854 (4)	1.2321 (3)	0.0489 (11)
H3	0.0431	0.7105	1.2825	0.059*
C4	0.3184 (9)	0.7676 (4)	1.1923 (2)	0.0455 (10)
H4	0.3281	0.8471	1.2154	0.055*
C5	0.4769 (8)	0.7344 (4)	1.1181 (2)	0.0390 (9)
C6	0.4513 (10)	0.6168 (4)	1.0883 (3)	0.0522 (12)
H6	0.5555	0.5913	1.0380	0.063*
C7	0.2807 (10)	0.5349 (4)	1.1288 (2)	0.0511 (11)
H7	0.2718	0.4547	1.1063	0.061*
C8	0.6638 (9)	0.8089 (4)	1.0680 (2)	0.0418 (10)
H8	0.7429	0.7691	1.0186	0.050*
C9	1.3189 (8)	0.9071 (4)	0.8487 (2)	0.0370 (9)
C10	1.6632 (9)	0.9110 (4)	0.7013 (3)	0.0469 (11)
H10A	1.7787	0.9530	0.7355	0.056*
H10B	1.8022	0.8559	0.6632	0.056*
C11	1.4718 (9)	1.0153 (4)	0.6522 (2)	0.0463 (10)
H11A	1.3404	1.0736	0.6903	0.056*
H11B	1.3482	0.9738	0.6203	0.056*
C12	1.6461 (9)	1.0959 (4)	0.5943 (2)	0.0467 (10)
H12A	1.7684	1.1383	0.6262	0.056*
H12B	1.7784	1.0378	0.5563	0.056*
C13	1.4508 (9)	1.1991 (4)	0.5453 (2)	0.0488 (11)
H13A	1.3236	1.1563	0.5154	0.059*
H13B	1.3227	1.2580	0.5837	0.059*
C14	1.6143 (10)	1.2790 (4)	0.4849 (3)	0.0545 (12)
H14A	1.7445	1.2204	0.4468	0.065*
H14B	1.7386	1.3235	0.5147	0.065*
C15	1.4131 (11)	1.3796 (5)	0.4361 (3)	0.0670 (14)
H15A	1.3058	1.3358	0.4015	0.100*
H15B	1.5293	1.4337	0.4019	0.100*
H15C	1.2742	1.4342	0.4735	0.100*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ni	0.0441 (7)	0.0337 (6)	0.0351 (5)	−0.0150 (4)	0.0033 (4)	0.0027 (4)
S1	0.0706 (9)	0.0392 (6)	0.0472 (6)	−0.0254 (6)	0.0172 (6)	−0.0036 (5)
S2	0.0571 (8)	0.0331 (6)	0.0520 (6)	−0.0121 (5)	0.0142 (5)	−0.0052 (4)
N1	0.044 (2)	0.0325 (16)	0.0337 (16)	−0.0097 (15)	0.0010 (14)	−0.0006 (13)
N2	0.045 (2)	0.0378 (18)	0.0370 (17)	−0.0105 (16)	0.0085 (15)	0.0032 (14)
C1	0.047 (3)	0.047 (2)	0.061 (3)	−0.016 (2)	−0.001 (2)	0.013 (2)
C2	0.034 (2)	0.042 (2)	0.050 (2)	−0.0104 (18)	−0.0010 (18)	0.0111 (18)
C3	0.051 (3)	0.044 (2)	0.051 (2)	−0.013 (2)	0.016 (2)	−0.0023 (19)
C4	0.053 (3)	0.034 (2)	0.049 (2)	−0.015 (2)	0.012 (2)	−0.0064 (17)
C5	0.040 (2)	0.039 (2)	0.038 (2)	−0.0142 (18)	0.0024 (18)	0.0049 (16)
C6	0.071 (3)	0.045 (2)	0.044 (2)	−0.027 (2)	0.013 (2)	−0.0083 (19)
C7	0.068 (3)	0.043 (2)	0.048 (2)	−0.027 (2)	0.004 (2)	−0.0037 (18)
C8	0.050 (3)	0.044 (2)	0.0337 (19)	−0.017 (2)	0.0048 (18)	−0.0028 (16)
C9	0.036 (2)	0.037 (2)	0.036 (2)	−0.0065 (18)	0.0024 (17)	0.0012 (16)
C10	0.049 (3)	0.039 (2)	0.050 (2)	−0.010 (2)	0.016 (2)	−0.0037 (18)
C11	0.050 (3)	0.044 (2)	0.045 (2)	−0.014 (2)	0.007 (2)	−0.0020 (18)
C12	0.048 (3)	0.043 (2)	0.049 (2)	−0.016 (2)	0.009 (2)	−0.0037 (18)
C13	0.051 (3)	0.050 (2)	0.047 (2)	−0.017 (2)	0.007 (2)	−0.0016 (19)
C14	0.061 (3)	0.047 (2)	0.056 (3)	−0.019 (2)	0.011 (2)	−0.001 (2)
C15	0.079 (4)	0.061 (3)	0.063 (3)	−0.026 (3)	0.001 (3)	0.007 (2)

Geometric parameters (Å, º) top

Ni—N1	1.933 (3)	C6—C7	1.385 (5)
Ni—N1ⁱ	1.933 (3)	C6—H6	0.9500
Ni—S1	2.1775 (10)	C7—H7	0.9500
Ni—S1ⁱ	2.1775 (10)	C8—H8	0.9500
S1—C9	1.720 (4)	C10—C11	1.519 (5)
S2—C9	1.757 (4)	C10—H10A	0.9900
S2—C10	1.811 (4)	C10—H10B	0.9900
N1—C8	1.294 (5)	C11—C12	1.521 (5)
N1—N2ⁱ	1.425 (4)	C11—H11A	0.9900
N2—C9	1.269 (5)	C11—H11B	0.9900
N2—N1ⁱ	1.425 (4)	C12—C13	1.521 (6)
C1—C2	1.501 (5)	C12—H12A	0.9900
C1—H1A	0.9800	C12—H12B	0.9900
C1—H1B	0.9800	C13—C14	1.513 (5)
C1—H1C	0.9800	C13—H13A	0.9900
C2—C3	1.371 (6)	C13—H13B	0.9900
C2—C7	1.391 (6)	C14—C15	1.517 (6)
C3—C4	1.383 (5)	C14—H14A	0.9900
C3—H3	0.9500	C14—H14B	0.9900
C4—C5	1.399 (5)	C15—H15A	0.9800
C4—H4	0.9500	C15—H15B	0.9800
C5—C6	1.387 (5)	C15—H15C	0.9800
C5—C8	1.452 (5)

N1—Ni—N1ⁱ	180.00 (14)	N2—C9—S1	125.9 (3)
N1—Ni—S1	93.96 (9)	N2—C9—S2	120.3 (3)
N1ⁱ—Ni—S1	86.04 (9)	S1—C9—S2	113.9 (2)
N1—Ni—S1ⁱ	86.04 (9)	C11—C10—S2	113.5 (3)
N1ⁱ—Ni—S1ⁱ	93.96 (9)	C11—C10—H10A	108.9
S1—Ni—S1ⁱ	180.0	S2—C10—H10A	108.9
C9—S1—Ni	95.86 (13)	C11—C10—H10B	108.9
C9—S2—C10	103.09 (19)	S2—C10—H10B	108.9
C8—N1—N2ⁱ	113.8 (3)	H10A—C10—H10B	107.7
C8—N1—Ni	126.3 (3)	C10—C11—C12	113.2 (3)
N2ⁱ—N1—Ni	119.9 (2)	C10—C11—H11A	108.9
C9—N2—N1ⁱ	111.9 (3)	C12—C11—H11A	108.9
C2—C1—H1A	109.5	C10—C11—H11B	108.9
C2—C1—H1B	109.5	C12—C11—H11B	108.9
H1A—C1—H1B	109.5	H11A—C11—H11B	107.8
C2—C1—H1C	109.5	C13—C12—C11	112.4 (3)
H1A—C1—H1C	109.5	C13—C12—H12A	109.1
H1B—C1—H1C	109.5	C11—C12—H12A	109.1
C3—C2—C7	117.1 (4)	C13—C12—H12B	109.1
C3—C2—C1	121.3 (4)	C11—C12—H12B	109.1
C7—C2—C1	121.7 (4)	H12A—C12—H12B	107.9
C2—C3—C4	123.0 (4)	C14—C13—C12	114.4 (4)
C2—C3—H3	118.5	C14—C13—H13A	108.7
C4—C3—H3	118.5	C12—C13—H13A	108.7
C3—C4—C5	120.4 (4)	C14—C13—H13B	108.7
C3—C4—H4	119.8	C12—C13—H13B	108.7
C5—C4—H4	119.8	H13A—C13—H13B	107.6
C6—C5—C4	116.3 (3)	C13—C14—C15	113.0 (4)
C6—C5—C8	116.0 (3)	C13—C14—H14A	109.0
C4—C5—C8	127.8 (4)	C15—C14—H14A	109.0
C7—C6—C5	122.9 (4)	C13—C14—H14B	109.0
C7—C6—H6	118.6	C15—C14—H14B	109.0
C5—C6—H6	118.6	H14A—C14—H14B	107.8
C6—C7—C2	120.3 (4)	C14—C15—H15A	109.5
C6—C7—H7	119.9	C14—C15—H15B	109.5
C2—C7—H7	119.9	H15A—C15—H15B	109.5
N1—C8—C5	133.6 (4)	C14—C15—H15C	109.5
N1—C8—H8	113.2	H15A—C15—H15C	109.5
C5—C8—H8	113.2	H15B—C15—H15C	109.5

C7—C2—C3—C4	0.8 (6)	C4—C5—C8—N1	2.7 (8)
C1—C2—C3—C4	−179.6 (4)	N1ⁱ—N2—C9—S1	1.8 (5)
C2—C3—C4—C5	−0.2 (7)	N1ⁱ—N2—C9—S2	−177.5 (2)
C3—C4—C5—C6	0.0 (6)	Ni—S1—C9—N2	2.5 (4)
C3—C4—C5—C8	179.5 (4)	Ni—S1—C9—S2	−178.24 (18)
C4—C5—C6—C7	−0.2 (7)	C10—S2—C9—N2	−0.4 (4)
C8—C5—C6—C7	−179.8 (4)	C10—S2—C9—S1	−179.8 (2)
C5—C6—C7—C2	0.8 (7)	C9—S2—C10—C11	−77.3 (3)
C3—C2—C7—C6	−1.0 (6)	S2—C10—C11—C12	−176.9 (3)
C1—C2—C7—C6	179.3 (4)	C10—C11—C12—C13	179.6 (3)
N2ⁱ—N1—C8—C5	−1.2 (7)	C11—C12—C13—C14	−178.2 (3)
Ni—N1—C8—C5	−179.8 (3)	C12—C13—C14—C15	179.1 (4)
C6—C5—C8—N1	−177.7 (4)

Symmetry code: (i) −x+2, −y+2, −z+2.

Experimental details

Crystal data
Chemical formula	[Ni(C₁₅H₂₁N₂S₂)₂]
M_r	645.62
Crystal system, space group	Triclinic, P1
Temperature (K)	173
a, b, c (Å)	4.6738 (3), 10.5132 (5), 16.4789 (8)
α, β, γ (°)	86.522 (3), 84.850 (3), 79.057 (3)
V (Å³)	791.00 (7)
Z	1
Radiation type	Cu Kα
µ (mm⁻¹)	3.55
Crystal size (mm)	0.37 × 0.08 × 0.02

Data collection
Diffractometer	Rigaku R-AXIS RAPID diffractometer
Absorption correction	Multi-scan (ABSCOR; Rigaku, 1995)
T_min, T_max	0.615, 0.932
No. of measured, independent and observed [F² > 2σ(F²)] reflections	9100, 2834, 2029
R_int	0.074
(sin θ/λ)_max (Å⁻¹)	0.602

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.071, 0.218, 1.09
No. of reflections	2834
No. of parameters	180
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.98, −0.35

Computer programs: RAPID-AUTO (Rigaku, 2001), SIR92 (Altomare et al., 1994), SHELXL97 (Sheldrick, 2008), CrystalStructure (Rigaku, 2010).

Selected geometric parameters (Å, º) top

Ni—N1	1.933 (3)	C2—C3	1.371 (6)
Ni—N1ⁱ	1.933 (3)	C2—C7	1.391 (6)
Ni—S1	2.1775 (10)	C3—C4	1.383 (5)
Ni—S1ⁱ	2.1775 (10)	C4—C5	1.399 (5)
S1—C9	1.720 (4)	C5—C6	1.387 (5)
S2—C9	1.757 (4)	C5—C8	1.452 (5)
S2—C10	1.811 (4)	C6—C7	1.385 (5)
N1—C8	1.294 (5)	C10—C11	1.519 (5)
N1—N2ⁱ	1.425 (4)	C11—C12	1.521 (5)
N2—C9	1.269 (5)	C12—C13	1.521 (6)
N2—N1ⁱ	1.425 (4)	C13—C14	1.513 (5)
C1—C2	1.501 (5)	C14—C15	1.517 (6)

N1—Ni—N1ⁱ	180.00 (14)	C3—C4—C5	120.4 (4)
N1—Ni—S1	93.96 (9)	C6—C5—C4	116.3 (3)
N1ⁱ—Ni—S1	86.04 (9)	C6—C5—C8	116.0 (3)
N1—Ni—S1ⁱ	86.04 (9)	C4—C5—C8	127.8 (4)
N1ⁱ—Ni—S1ⁱ	93.96 (9)	C7—C6—C5	122.9 (4)
S1—Ni—S1ⁱ	180.0	C6—C7—C2	120.3 (4)
C9—S1—Ni	95.86 (13)	N1—C8—C5	133.6 (4)
C9—S2—C10	103.09 (19)	N2—C9—S1	125.9 (3)
C8—N1—N2ⁱ	113.8 (3)	N2—C9—S2	120.3 (3)
C8—N1—Ni	126.3 (3)	S1—C9—S2	113.9 (2)
N2ⁱ—N1—Ni	119.9 (2)	C11—C10—S2	113.5 (3)
C9—N2—N1ⁱ	111.9 (3)	C10—C11—C12	113.2 (3)
C3—C2—C7	117.1 (4)	C13—C12—C11	112.4 (3)
C3—C2—C1	121.3 (4)	C14—C13—C12	114.4 (4)
C7—C2—C1	121.7 (4)	C13—C14—C15	113.0 (4)
C2—C3—C4	123.0 (4)

Symmetry code: (i) −x+2, −y+2, −z+2.

Acknowledgements

MBHH and MSB are grateful to the Department of Chemistry, Rajshahi University, for the provision of laboratory facilities. MCS acknowledges the Department of Applied Chemistry, Toyama University, for providing funds for single-crystal X-ray analyses.

References

Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M. C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435. CrossRef Web of Science IUCr Journals Google Scholar
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Volume 71| Part 2| February 2015| Pages m26-m27

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