Crystal structure of bis­{S-octyl-3-[(thio­phen-2-yl)methyl­idene]di­thio­carbazato-κ2N3,S}nickel(II)

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

doi:10.1107/S2056989023005935

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ISSN: 2056-9890

Volume 79| Part 8| August 2023| Pages 714-717

https://doi.org/10.1107/S2056989023005935

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Crystal structure of bis{S-octyl-3-[(thiophen-2-yl)methylidene]dithiocarbazato-κ²N³,S}nickel(II)

Sultana Shakila Khan,^a Md. Belayet Hossain Howlader,^a ^* Md. Chanmiya Sheikh,^b Ryuta Miyatake ^c and Ennio Zangrando ^d

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

Edited by S. Parkin, University of Kentucky, USA (Received 6 June 2023; accepted 6 July 2023; online 11 July 2023)

In the title complex, [Ni(C₁₄H₂₁N₂S₃)₂], the nickel(II) atom is located on a crystallographic inversion center and exhibits a square-planar coordination environment, being coordinated by two negatively charged N,S-chelating ligands in a trans configuration. In the crystal, the non-H atoms of the complex are practically coplanar (r.m.s. deviation of fitted atoms = 0.135 Å), and the angle between the thienyl and the chelating rings is 6.7 (1)°. The molecules stack at a distance of 3.623 (2) Å along the b-axis direction.

Keywords: crystal structure; nickel(II) complex; dithiocarbazato ligand.

CCDC reference: 2254902

1. Chemical context

Thiosemicarbazones, semicarbazones, hydrazide/hydrazones and dithiocarbazate ligands have been widely employed for the preparation of metal complexes. Over the last few decades, dithiocarbazate Schiff bases and their metal complexes have gained considerable interest because of their promising bioactivities against diverse cancer cell lines (Yusof et al., 2015 ; Ramilo-Gomes et al., 2021 ; Low et al., 2016 ), as well as antimicrobial activity (Zangrando et al., 2017 ). Clearly, the biological properties of these compounds can be modulated by using different organic substituents, leading to concomitant structural modifications (How et al., 2008 ; Yusof et al., 2022 ). A study of structure–activity relationships was described by Beshir et al. (2008 ).

Therefore, considering the diverse significance of dithiocarbazate bases and their role in a variety of biological applications, herein we report a novel Ni^II complex with a dithiocarbazate Schiff base ligand bearing an octyl alkyl chain and a thienyl ring (Fig. 1).

Figure 1
An ellipsoid plot (50% probability) of the title compound.

2. Structural commentary

The nickel(II) atom is located on a crystallographic center of symmetry and exhibits a square-planar coordination sphere, being coordinated by two negatively charged N,S-chelating ligands in a trans configuration. The Ni—N1 and Ni—S1 bond distances are 1.9168 (19) and 2.1735 (7) Å, respectively with a chelating N1—Ni—S1 bond angle of 85.88 (6)°. These values agree with those reported in previous papers (Begum et al., 2016 ; Islam et al., 2014 ; Howlader et al., 2015 ) for related compounds. It is worth mentioning that nickel(II) and copper(II) complexes with dithiocarbazate ligands have been reported to crystallize in both cis and trans configurations, although the latter is slightly more frequent (Begum et al., 2020 ).

All of the non-H atoms of the complex are almost coplanar, with S1 and C1 [−0.28 Å] and C13, C14 [+0.24, +0.31 Å], respectively deviating the most from its mean plane (r.m.s. deviation of fitted atoms = 0.135 Å). The thienyl ring forms a small dihedral angle of 6.7 (1)° with respect to the chelating five-membered ring. The long alkyl chain is in a staggered conformation with torsion angles along the chain that range between 176.7 (2) and 179.8 (2)°.

The molecule is stabilized by an intramolecular unconventional hydrogen bond between C5—H5 with S1′ [at 1 − x, 1 − y, 1 − z] of the symmetry-related ligand [C5⋯S1′ distance of 3.067 (3) Å, C5—H5⋯S1′ angle of 125°].

3. Supramolecular features

The molecules stack with an interplanar distance of 3.623 (2) Å, and the crystal packing shows that all hydrophobic n-octyl chains segregate together, so as to share the same regions of space (Fig. 2), as already observed in similar complexes (Begum et al., 2016). Fig. 3 overlays this structure of the complex superimposed onto that of a 4-methoxybenzyl derivative (WEGKEB: Begum et al., 2018 ), where it is worth noting the different orientation of octyl chains in the two cases. This is due to the different torsion angle C6—S2—C7—C8 of −177.36 (18)° in this structure vs 86.8 (6)° and −160.0 (9)° (for the two disorder components of the equivalent torsion angle in WEGKEB), likely induced by crystal-packing requirements. Details of hydrogen-bonding interactions are given in Table 1.

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯S1ⁱ	0.95	3.00	3.684 (3)	131
C2—H2⋯S2ⁱⁱ	0.95	2.93	3.752 (3)	146
C5—H5⋯S1ⁱⁱⁱ	0.95	2.42	3.067 (3)	125
C7—H7A⋯S3	0.99	2.93	3.406 (3)	110
Symmetry codes: (i) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (ii) $[x, -y-{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (iii) .

Figure 2
A partial packing view showing complexes stacked in the b-axis direction.

Figure 3
Superposition of this structure with the 4-methoxybenzyl derivative WEGKEB (Begum et al., 2018

; only one disorder component shown), where it is worth noting the different orientation of the octyl moiety, likely induced by crystal-packing requirements.

4. Database survey

For comparison, Ni^II complexes with comparable ligands bearing long alkyl chains have been reported from these laboratories (Begum et al., 2016, 2017 , 2018, 2020, 2023 ; CSD refcodes = JUYCAJ, WEGKEB, BIQTIH, TILVUJ and PICMOH, respectively).

5. Synthesis and crystallization

A solution of Ni(CH₃COO)₂·4H₂O (0.12 g, 0.5 mmol in 10 mL methanol) was added to a solution of S-octyl-β-N-(2-thienyl)methylenedithiocarbazate (0.314 g, 1.0 mmol in 30 mL of methanol). The resulting mixture was stirred at room temperature for 4 h. The dark-orange precipitate that formed was filtered off, washed with methanol and dried in vacuo over anhydrous CaCl₂. Orange needle-shaped single crystals, suitable for X-ray diffraction, were obtained by slow evaporation of the compound from a mixture of chloroform and acetonitrile (4:1, v/v) after 14 days. Yield: 66%; m. p. (377-378) K.

FT–IR (KBr, cm⁻¹): 2920 ν(C—H, alkyl), 1639, 1572 ν(C=N—N=C).

¹H NMR (400 MHz, CDCl₃, ppm) δ: 7.999 (s, 2×1H, CH=N, C-5), 7.715 (d, 2×1H, C-1, J = 5.2 Hz), 7.468 (d, 2×1H, C-3, J = 5.2 Hz), 7.103 (t, 2×1H, C-2), 3.269 (t, 2×2H, –SCH₂, C-7), 1.764 (p, 2×2H, C-8), 1.460 (p, 2×2H, C-9), 1.318–1.270 (m, 2×8H, C-10, 11, 12, 13), 0.878 (t, 2×3H, C-14).

UV–Vis spectrum [CHCl₃, λ_max nm]: 475, 400, 276.

HRMS (FAB) Calculated for C₂₈H₄₂N₄NiS₆ [M+H]⁺: 685.11599, found [M+H]⁺: 685.11549.

6. Refinement

Crystal data, data collection and structure refinement are summarized in Table 2. Hydrogen atoms were placed at calculated positions (C–H = 0.95–0.99 Å) and refined as riding with U_iso(H) = 1.2–1.5U_eq(C).

Table 2
Experimental details

Crystal data
Chemical formula	[Ni(C₁₄H₂₁N₂S₃)₂]
M_r	685.72
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	173
a, b, c (Å)	15.5444 (6), 5.5388 (3), 20.1592 (8)
β (°)	103.675 (7)
V (Å³)	1686.44 (13)
Z	2
Radiation type	Mo Kα
μ (mm⁻¹)	0.97
Crystal size (mm)	0.08 × 0.02 × 0.01

Data collection
Diffractometer	Rigaku R-AXIS RAPID
Absorption correction	Multi-scan (ABSCOR; Rigaku, 1995 )
T_min, T_max	0.815, 0.990
No. of measured, independent and observed [I > 2σ(I)] reflections	15791, 3850, 2621
R_int	0.077
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.045, 0.079, 1.00
No. of reflections	3850
No. of parameters	179
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.44, −0.27
Computer programs: RAPID-AUTO (Rigaku, 2018 ), SHELXT (Sheldrick, 2015a ), SHELXL2019/2 (Sheldrick, 2015b ), DIAMOND (Brandenburg, 1999 ) and WinGX (Farrugia, 2012 ).

Supporting information

CCDC reference: 2254902

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S2056989023005935/pk2690sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989023005935/pk2690Isup2.hkl

checkCIF report

Computing details top

Data collection: RAPID-AUTO (Rigaku, 2018); cell refinement: RAPID-AUTO (Rigaku, 2018); data reduction: RAPID-AUTO (Rigaku, 2018); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2019/2 (Sheldrick, 2015b); molecular graphics: DIAMOND (Brandenburg, 1999); software used to prepare material for publication: WinGX (Farrugia, 2012).

Bis{S-octyl-3-[(thiophen-2-yl)methylidene]dithiocarbazato-κ²N³,S}nickel(II) top

Crystal data top

[Ni(C₁₄H₂₁N₂S₃)₂]	F(000) = 724
M_r = 685.72	D_x = 1.350 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71075 Å
a = 15.5444 (6) Å	Cell parameters from 10434 reflections
b = 5.5388 (3) Å	θ = 2.1–27.5°
c = 20.1592 (8) Å	µ = 0.97 mm⁻¹
β = 103.675 (7)°	T = 173 K
V = 1686.44 (13) Å³	Needle, orange
Z = 2	0.08 × 0.02 × 0.01 mm

Data collection top

Rigaku R-AXIS RAPID diffractometer	2621 reflections with I > 2σ(I)
Detector resolution: 10.000 pixels mm^-1	R_int = 0.077
ω scans	θ_max = 27.5°, θ_min = 2.7°
Absorption correction: multi-scan (ABSCOR; Rigaku, 1995)	h = −19→20
T_min = 0.815, T_max = 0.990	k = −7→7
15791 measured reflections	l = −26→25
3850 independent reflections

Refinement top

Refinement on F²	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.045	H-atom parameters constrained
wR(F²) = 0.079	w = 1/[σ²(F_o²) + (0.0329P)² + 0.0128P] where P = (F_o² + 2F_c²)/3
S = 1.00	(Δ/σ)_max = 0.001
3850 reflections	Δρ_max = 0.44 e Å⁻³
179 parameters	Δρ_min = −0.27 e Å⁻³

Special details top

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

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

	x	y	z	U_iso*/U_eq
Ni1	0.500000	0.500000	0.500000	0.02461 (12)
S1	0.43249 (4)	0.34173 (13)	0.57239 (3)	0.03295 (17)
S2	0.30020 (4)	−0.04469 (12)	0.55073 (3)	0.03283 (17)
S3	0.33321 (4)	−0.17114 (13)	0.33566 (3)	0.03364 (17)
N1	0.43677 (12)	0.2681 (4)	0.43617 (10)	0.0263 (5)
N2	0.37776 (13)	0.1034 (4)	0.45452 (10)	0.0274 (5)
C1	0.32299 (17)	−0.2689 (5)	0.25377 (13)	0.0364 (7)
H1	0.290649	−0.408991	0.235505	0.044*
C2	0.36579 (17)	−0.1259 (5)	0.21773 (13)	0.0384 (7)
H2	0.366185	−0.152919	0.171263	0.046*
C3	0.40956 (16)	0.0668 (5)	0.25668 (12)	0.0331 (6)
H3	0.443110	0.184342	0.239444	0.040*
C4	0.39872 (15)	0.0677 (4)	0.32296 (12)	0.0273 (6)
C5	0.44139 (15)	0.2400 (5)	0.37290 (12)	0.0289 (6)
H5	0.478965	0.351305	0.357540	0.035*
C6	0.37280 (14)	0.1323 (4)	0.51739 (12)	0.0255 (5)
C7	0.25455 (16)	−0.2377 (5)	0.47858 (12)	0.0317 (6)
H7A	0.228117	−0.136545	0.438453	0.038*
H7B	0.302730	−0.334361	0.467263	0.038*
C8	0.18415 (17)	−0.4070 (5)	0.49347 (13)	0.0338 (6)
H8A	0.210547	−0.512821	0.532553	0.041*
H8B	0.136169	−0.311795	0.505600	0.041*
C9	0.14665 (17)	−0.5596 (5)	0.43057 (13)	0.0364 (7)
H9A	0.123844	−0.450452	0.391478	0.044*
H9B	0.195365	−0.655482	0.419806	0.044*
C10	0.07291 (17)	−0.7307 (5)	0.43757 (13)	0.0368 (6)
H10A	0.025185	−0.637168	0.450618	0.044*
H10B	0.096283	−0.847621	0.474588	0.044*
C11	0.03444 (17)	−0.8679 (5)	0.37195 (13)	0.0393 (7)
H11A	0.011898	−0.749798	0.335090	0.047*
H11B	0.082584	−0.960448	0.359172	0.047*
C12	−0.03979 (17)	−1.0408 (5)	0.37605 (14)	0.0403 (7)
H12A	−0.016871	−1.163148	0.411632	0.048*
H12B	−0.087282	−0.949827	0.390228	0.048*
C13	−0.0790 (2)	−1.1686 (7)	0.30929 (15)	0.0569 (9)
H13A	−0.102651	−1.046174	0.273913	0.068*
H13B	−0.031228	−1.257274	0.294768	0.068*
C14	−0.1521 (2)	−1.3442 (7)	0.31334 (18)	0.0693 (11)
H14A	−0.128788	−1.469718	0.347054	0.083*
H14B	−0.174872	−1.418856	0.268549	0.083*
H14C	−0.200158	−1.257687	0.327044	0.083*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ni1	0.0294 (2)	0.0213 (3)	0.0228 (2)	−0.0016 (2)	0.00554 (18)	−0.00261 (19)
S1	0.0420 (4)	0.0320 (4)	0.0256 (3)	−0.0103 (3)	0.0095 (3)	−0.0052 (3)
S2	0.0415 (4)	0.0294 (4)	0.0287 (3)	−0.0086 (3)	0.0105 (3)	0.0004 (3)
S3	0.0419 (4)	0.0278 (4)	0.0300 (3)	−0.0062 (3)	0.0062 (3)	−0.0026 (3)
N1	0.0299 (11)	0.0220 (12)	0.0270 (11)	−0.0014 (9)	0.0067 (9)	−0.0013 (9)
N2	0.0345 (11)	0.0225 (12)	0.0265 (11)	−0.0050 (9)	0.0098 (9)	−0.0008 (9)
C1	0.0406 (15)	0.0330 (17)	0.0324 (14)	−0.0041 (13)	0.0021 (12)	−0.0101 (12)
C2	0.0391 (15)	0.0460 (19)	0.0297 (13)	−0.0038 (13)	0.0076 (13)	−0.0126 (13)
C3	0.0365 (14)	0.0368 (17)	0.0265 (12)	−0.0044 (12)	0.0087 (12)	−0.0051 (11)
C4	0.0298 (13)	0.0232 (14)	0.0278 (12)	−0.0008 (10)	0.0046 (11)	−0.0025 (10)
C5	0.0327 (13)	0.0260 (15)	0.0298 (13)	−0.0038 (11)	0.0109 (11)	−0.0015 (11)
C6	0.0270 (12)	0.0202 (14)	0.0285 (13)	0.0008 (10)	0.0049 (11)	0.0037 (10)
C7	0.0377 (14)	0.0261 (15)	0.0306 (13)	−0.0045 (11)	0.0068 (12)	−0.0009 (11)
C8	0.0373 (14)	0.0291 (15)	0.0347 (14)	−0.0064 (11)	0.0077 (12)	0.0019 (11)
C9	0.0379 (14)	0.0314 (17)	0.0398 (15)	−0.0074 (12)	0.0091 (13)	−0.0027 (12)
C10	0.0397 (14)	0.0300 (16)	0.0421 (15)	−0.0072 (12)	0.0122 (13)	−0.0020 (12)
C11	0.0396 (15)	0.0370 (18)	0.0405 (15)	−0.0097 (13)	0.0078 (13)	−0.0037 (13)
C12	0.0419 (15)	0.0355 (18)	0.0430 (15)	−0.0089 (13)	0.0090 (13)	−0.0027 (13)
C13	0.0565 (19)	0.060 (2)	0.0522 (19)	−0.0206 (17)	0.0084 (16)	−0.0114 (17)
C14	0.063 (2)	0.062 (3)	0.072 (2)	−0.0261 (19)	−0.0053 (19)	−0.009 (2)

Geometric parameters (Å, º) top

Ni1—N1ⁱ	1.9168 (19)	C7—H7B	0.9900
Ni1—N1	1.9168 (19)	C8—C9	1.521 (3)
Ni1—S1ⁱ	2.1735 (7)	C8—H8A	0.9900
Ni1—S1ⁱ	2.1735 (7)	C8—H8B	0.9900
Ni1—S1	2.1735 (7)	C9—C10	1.519 (3)
S1—C6	1.717 (2)	C9—H9A	0.9900
S2—C6	1.745 (2)	C9—H9B	0.9900
S2—C7	1.809 (2)	C10—C11	1.520 (3)
S3—C1	1.709 (3)	C10—H10A	0.9900
S3—C4	1.725 (3)	C10—H10B	0.9900
N1—C5	1.304 (3)	C11—C12	1.516 (4)
N1—N2	1.404 (3)	C11—H11A	0.9900
N2—C6	1.298 (3)	C11—H11B	0.9900
C1—C2	1.351 (4)	C12—C13	1.515 (4)
C1—H1	0.9500	C12—H12A	0.9900
C2—C3	1.402 (4)	C12—H12B	0.9900
C2—H2	0.9500	C13—C14	1.513 (4)
C3—C4	1.386 (3)	C13—H13A	0.9900
C3—H3	0.9500	C13—H13B	0.9900
C4—C5	1.431 (3)	C14—H14A	0.9800
C5—H5	0.9500	C14—H14B	0.9800
C7—C8	1.524 (3)	C14—H14C	0.9800
C7—H7A	0.9900

N1ⁱ—Ni1—N1	180.0	C9—C8—H8A	109.8
N1ⁱ—Ni1—S1ⁱ	85.88 (6)	C7—C8—H8A	109.8
N1—Ni1—S1ⁱ	94.12 (6)	C9—C8—H8B	109.8
N1ⁱ—Ni1—S1ⁱ	85.88 (6)	C7—C8—H8B	109.8
N1—Ni1—S1ⁱ	94.12 (6)	H8A—C8—H8B	108.3
S1ⁱ—Ni1—S1ⁱ	0.00 (2)	C10—C9—C8	114.7 (2)
N1ⁱ—Ni1—S1	94.12 (6)	C10—C9—H9A	108.6
N1—Ni1—S1	85.88 (6)	C8—C9—H9A	108.6
S1ⁱ—Ni1—S1	180.0	C10—C9—H9B	108.6
S1ⁱ—Ni1—S1	180.0	C8—C9—H9B	108.6
C6—S1—Ni1	96.42 (8)	H9A—C9—H9B	107.6
C6—S2—C7	100.88 (12)	C9—C10—C11	112.4 (2)
C1—S3—C4	91.32 (13)	C9—C10—H10A	109.1
C5—N1—N2	111.8 (2)	C11—C10—H10A	109.1
C5—N1—Ni1	126.77 (17)	C9—C10—H10B	109.1
N2—N1—Ni1	121.46 (14)	C11—C10—H10B	109.1
C6—N2—N1	111.74 (19)	H10A—C10—H10B	107.9
C2—C1—S3	112.9 (2)	C12—C11—C10	114.6 (2)
C2—C1—H1	123.6	C12—C11—H11A	108.6
S3—C1—H1	123.6	C10—C11—H11A	108.6
C1—C2—C3	112.4 (2)	C12—C11—H11B	108.6
C1—C2—H2	123.8	C10—C11—H11B	108.6
C3—C2—H2	123.8	H11A—C11—H11B	107.6
C4—C3—C2	112.9 (2)	C13—C12—C11	113.4 (2)
C4—C3—H3	123.5	C13—C12—H12A	108.9
C2—C3—H3	123.5	C11—C12—H12A	108.9
C3—C4—C5	122.6 (2)	C13—C12—H12B	108.9
C3—C4—S3	110.53 (18)	C11—C12—H12B	108.9
C5—C4—S3	126.78 (19)	H12A—C12—H12B	107.7
N1—C5—C4	130.1 (2)	C14—C13—C12	113.7 (3)
N1—C5—H5	115.0	C14—C13—H13A	108.8
C4—C5—H5	115.0	C12—C13—H13A	108.8
N2—C6—S1	124.49 (19)	C14—C13—H13B	108.8
N2—C6—S2	119.99 (18)	C12—C13—H13B	108.8
S1—C6—S2	115.51 (14)	H13A—C13—H13B	107.7
C8—C7—S2	111.63 (17)	C13—C14—H14A	109.5
C8—C7—H7A	109.3	C13—C14—H14B	109.5
S2—C7—H7A	109.3	H14A—C14—H14B	109.5
C8—C7—H7B	109.3	C13—C14—H14C	109.5
S2—C7—H7B	109.3	H14A—C14—H14C	109.5
H7A—C7—H7B	108.0	H14B—C14—H14C	109.5
C9—C8—C7	109.2 (2)

C5—N1—N2—C6	−179.6 (2)	N1—N2—C6—S1	−1.3 (3)
Ni1—N1—N2—C6	0.4 (3)	N1—N2—C6—S2	177.52 (15)
C4—S3—C1—C2	−1.0 (2)	Ni1—S1—C6—N2	1.4 (2)
S3—C1—C2—C3	0.9 (3)	Ni1—S1—C6—S2	−177.45 (11)
C1—C2—C3—C4	−0.3 (3)	C7—S2—C6—N2	2.3 (2)
C2—C3—C4—C5	176.5 (2)	C7—S2—C6—S1	−178.84 (14)
C2—C3—C4—S3	−0.5 (3)	C6—S2—C7—C8	−177.36 (18)
C1—S3—C4—C3	0.8 (2)	S2—C7—C8—C9	178.55 (18)
C1—S3—C4—C5	−176.0 (2)	C7—C8—C9—C10	−177.8 (2)
N2—N1—C5—C4	−2.1 (4)	C8—C9—C10—C11	176.7 (2)
Ni1—N1—C5—C4	177.9 (2)	C9—C10—C11—C12	−179.8 (2)
C3—C4—C5—N1	178.5 (3)	C10—C11—C12—C13	178.0 (3)
S3—C4—C5—N1	−5.1 (4)	C11—C12—C13—C14	179.1 (3)

Symmetry code: (i) −x+1, −y+1, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···S1ⁱⁱ	0.95	3.00	3.684 (3)	131
C2—H2···S2ⁱⁱⁱ	0.95	2.93	3.752 (3)	146
C5—H5···S1ⁱ	0.95	2.42	3.067 (3)	125
C7—H7A···S3	0.99	2.93	3.406 (3)	110

Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x, −y+1/2, z−1/2; (iii) x, −y−1/2, z−1/2.

Acknowledgements

MBHH and SSK are grateful to the Department of Chemistry, Rajshahi University for the provision of laboratory facilities. MCS and RM acknowledge the Center for Environmental Conservation and Research Safety, University of Toyama, for providing facilities for single-crystal X-ray analyses.

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