Bis[S-octyl 3-(2-methyl­propyl­idene)di­thio­carb­az­ato-κ2N3,S]nickel(II)

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

doi:10.1107/S241431462400186X

metal-organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 9| Part 3| March 2024| x240186

https://doi.org/10.1107/S241431462400186X

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Bis[S-octyl 3-(2-methylpropylidene)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 M. Weil, Vienna University of Technology, Austria (Received 30 January 2024; accepted 26 February 2024; online 6 March 2024)

The central Ni^II atom in the title complex, [Ni(C₁₃H₂₅N₂S₂)₂], is located on an inversion center and adopts a roughly square-planar coordination environment defined by two chelating N,S donor sets of two symmetry-related ligands in a trans configuration. The Ni—N and Ni—S bond lenghts are 1.9193 (14) and 2.1788 (5) Å, respectively, with a chelating N—Ni—S bond angle of 86.05 (4)°. These data are compared with those measured for similar dithiocarbazato ligands that bear n-octyl or n-hexyl alkyl chains. Slight differences are observed with respect to the phenylethylidene derivative where the ligands are bound cis relative to one another.

Keywords: crystal structure; dithiocarbazato ligand; Ni^II complex; trans configuration complex; octyl alkyl chain.

CCDC reference: 2335121

Structure description

Dithiocarbazate Schiff base derivatives have emerged as prospective ligands in medicinal chemistry as a result of their various pharmaceutical and biological activities (Gou et al., 2022 ; Low et al., 2016 ; Malik et al., 2020 ). For some years, we have been undertaking a study of N,S-chelating dithiocarbazato ligands and their corresponding metal complexes, which were observed to crystallize with ligands both in trans and cis configurations (Begum et al., 2020 ). Considering the above aspects, and in a continuation of our research, we report herein a novel Ni^II complex with a dithiocarbazato Schiff base ligand bearing an octyl alkyl chain.

In the title complex (Fig. 1), [Ni(C₁₃H₂₅N₂S₂)₂], the Ni^II atom is located on an inversion center and exhibits a square-planar coordination environment, defined by two negatively charged N,S-chelating ligands in a trans configuration. The Ni—N1 and Ni—S1 bond lengths are 1.9193 (14) and 2.1788 (5) Å, respectively, with a chelating N1—Ni—S1 bond angle of 86.05 (4)°. With the exception of methyl groups C1 and C2, all of the non-H atoms of the title complex are coplanar, with Ni1 (+0.16 Å) and S1 (–0.15 Å) deviating the most from the least-squares plane (r.m.s. deviation of fitted atoms = 0.073 Å). The long alkyl chain is in a staggered conformation with torsion angles along the chain between 178.20 (19) and 179.81 (15)°. The molecular structure is stabilized by an intramolecular non-conventional C4—H4⋯S1ⁱ hydrogen bond with a C4⋯S1ⁱ distance of 3.0965 (16) Å and a C4—H4⋯S1ⁱ angle of 121° [symmetry code: (i): 1 − x, 1 − y, 1 − z].

Figure 1
Molecular structure of the title complex [Ni(C₁₃H₂₅N₂S₂)₂] with displacement ellipsoids drawn at the 50% probability level.

A number of Ni^II complexes with ligands bearing n-octyl or n-hexyl alkyl chains have been structurally characterized and a comparison of relevant bond lengths and angles is compiled in Table 1. The corresponding values reported above are consistent with those measured in bis-chelated Ni^II complexes built with similar ligands bearing a methoxybenzylidene (Begum et al., 2018 ) or thiophenmethylidene (Khan et al., 2023a ) ligand. On the contrary, in the phenylethylidene complex (Khan et al., 2023b ) the two independent Ni—N bond lengths are 0.02 Å longer with respect to those calculated in the present work, while the Ni—S ones are shorter by ca 0.02 Å. It is worth noting that the latter complex exhibits a cis configuration of the ligands. A similar trend is also observed in the complex with the S-n-hexyl 3-(1-phenylethylidene)dithiocarbazate ligand (Begum et al., 2020). Nickel(II) and copper(II) complexes with dithiocarbazato ligands have been reported to crystallize in both cis and trans configurations, although the latter are slightly more frequent (Begum et al., 2020). However, the chelating N,S bond angles in these complexes are similar within their standard deviations and fall into the range 85.67 (5)–86.40 (5)°.

Table 1
Comparative geometrical parameters (Å, °) for bis-chelated Ni complexes with dithiocarbazato ligands bearing an S-octyl/S-hexyl (n) alkyl chain

Complex	CSD Refcode	n	Ni—N	Ni—S	N—Ni—S
This work	–	8	1.9193 (14)	2.1788 (5)	86.05 (4)
1	BIQTIH	8	1.9310 (19)	2.1796 (6)	85.67 (5)
2	MIMTIG	8	1.9168 (19)	2.1735 (7)	85.88 (6)
3, ligand 1	QIVYUT	8	1.9318 (16)	2.1506 (6)	86.26 (5)
3, ligand 2	QIVYUT	8	1.9392 (16)	2.1573 (6)	86.40 (5)
4	LUBYAK	6	1.933 (3)	2.1775 (10)	86.04 (9)
5, ligand 1	JUYCAJ	6	1.9112 (12)	2.1785 (4)	85.74 (3)
5, ligand 2	JUYCAJ	6	1.9177 (12)	2.1812 (4)	86.03 (4)
6	WEGKEB	6	1.915 (2)	2.1788 (8)	85.58 (8)
7	TILVUJ	6	1.9295 (10)	2.1600 (4)	85.68 (3)
Notes: Complex 1 (Begum et al., 2018); 2 (Kahn et al., 2023a); 3 (Kahn et al., 2023b); 4 (Howlader et al., 2015 ); 5 (Begum et al., 2016 ); 6 (Begum et al., 2017 ); 7 (Begum et al., 2020). Complexes 3 and 7 show a cis configuration of ligands.

The packing of the complex is shown in Fig. 2; the complexes stack with an Ni⋯Ni separation of 7.8973 (2) Å along the c axis.

Figure 2
View of the crystal packing of the title complex [Ni(C₁₃H₂₅N₂S₂)₂] in a view along [102]; H atoms are not shown for clarity.

Synthesis and crystallization

A solution of Ni(CH₃COO)₂·4H₂O (0.124 g, 0.5 mmol) in 10 ml of methanol was added to a solution of S-octyl-3-(2-methylpropylidene)dithiocarbazate (0.274 g, 1.0 mmol) in 30 ml of methanol. The resulting mixture was stirred at room temperature for 5 h. The green precipitate that formed was filtered off, washed with methanol and dried in vacuo over anhydrous CaCl₂. Green single crystals of the title compound suitable for X-ray diffraction were obtained by slow evaporation from a mixture of chloroform and acetonitrile (1:1, v/v) after 7 d.

Yield: 72%; m. p. 333–334 K. FT–IR (KBr discs, cm⁻¹): ν(C—H, alkyl) 2964, 2922, ν(C=N—N=C) 1634. ¹H NMR (400 MHz, CDCl₃, p.p.m.) δ: 6.99 (d, 2×1H, C-4, CH=N), 3.29 (m, 2×1H, C-3), 2.98 (t, 2×2H, C-6, –SCH₂), 1.65 (m, 2×2H, C-7), 1.38–1.12 (m, 2×10H, C-8, 9, 10, 11, 12), 1.00 (d, 2×6H, C-1, 2, CH₃), 0.87 (t, 2×3H, C-13, CH₃). HRMS (FAB) Calculated for C₂₆H₅₀N₄NiS₄ [M + H]⁺: 605.23494, found [M + H]⁺: 605.23445.

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2.

Table 2
Experimental details

Crystal data
Chemical formula	[Ni(C₁₃H₂₅N₂S₂)₂]
M_r	605.65
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	173
a, b, c (Å)	11.5962 (4), 18.4606 (5), 7.8973 (2)
β (°)	106.532 (7)
V (Å³)	1620.71 (10)
Z	2
Radiation type	Mo Kα
μ (mm⁻¹)	0.88
Crystal size (mm)	0.18 × 0.06 × 0.02

Data collection
Diffractometer	Rigaku R-AXIS RAPID
Absorption correction	Multi-scan (ABSCOR; Rigaku, 1995 )
T_min, T_max	0.781, 0.983
No. of measured, independent and observed [I > 2σ(I)] reflections	15550, 3702, 2920
R_int	0.049
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.036, 0.072, 1.04
No. of reflections	3702
No. of parameters	163
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.37, −0.21
Computer programs: RAPID-AUTO (Rigaku, 2018 ), SHELXT (Sheldrick, 2015a ), SHELXL (Sheldrick, 2015b ), DIAMOND (Brandenburg, 1999 ) and WinGX publication routines (Farrugia, 2012 ).

Structural data

CCDC reference: 2335121

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S241431462400186X/wm4208sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S241431462400186X/wm4208Isup2.hkl

checkCIF report

Computing details top

Bis[S-octyl 3-(2-methylpropylidene)dithiocarbazato-κ²N³,S]nickel(II) top

Crystal data top

[Ni(C₁₃H₂₅N₂S₂)₂]	F(000) = 652
M_r = 605.65	D_x = 1.241 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71075 Å
a = 11.5962 (4) Å	Cell parameters from 11425 reflections
b = 18.4606 (5) Å	θ = 1.8–27.5°
c = 7.8973 (2) Å	µ = 0.88 mm⁻¹
β = 106.532 (7)°	T = 173 K
V = 1620.71 (10) Å³	Platelet, green
Z = 2	0.18 × 0.06 × 0.02 mm

Data collection top

Rigaku R-AXIS RAPID diffractometer	2920 reflections with I > 2σ(I)
Detector resolution: 10.000 pixels mm^-1	R_int = 0.049
ω scans	θ_max = 27.5°, θ_min = 2.2°
Absorption correction: multi-scan (ABSCOR; Rigaku, 1995)	h = −15→15
T_min = 0.781, T_max = 0.983	k = −23→23
15550 measured reflections	l = −10→9
3702 independent reflections

Refinement top

Refinement on F²	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.036	H-atom parameters constrained
wR(F²) = 0.072	w = 1/[σ²(F_o²) + (0.0305P)² + 0.4396P] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max = 0.001
3702 reflections	Δρ_max = 0.37 e Å⁻³
163 parameters	Δρ_min = −0.21 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	0.02167 (9)
S1	0.60829 (5)	0.43196 (2)	0.71132 (6)	0.02979 (12)
S2	0.72948 (5)	0.47341 (3)	1.07771 (6)	0.02978 (12)
N1	0.50276 (14)	0.56970 (8)	0.68145 (18)	0.0234 (3)
N2	0.58197 (14)	0.56067 (8)	0.85404 (18)	0.0256 (3)
C1	0.3208 (2)	0.71961 (11)	0.7769 (3)	0.0404 (5)
H1A	0.324068	0.754490	0.871744	0.049*
H1B	0.258003	0.683641	0.773519	0.049*
H1C	0.302375	0.745114	0.663553	0.049*
C2	0.5430 (2)	0.73600 (11)	0.8188 (3)	0.0428 (5)
H2A	0.526392	0.761787	0.705932	0.051*
H2B	0.619737	0.710216	0.841194	0.051*
H2C	0.547434	0.770833	0.914072	0.051*
C3	0.44208 (19)	0.68158 (10)	0.8112 (2)	0.0313 (5)
H3	0.459840	0.655777	0.927134	0.038*
C4	0.43794 (19)	0.62718 (10)	0.6691 (2)	0.0296 (4)
H4	0.381339	0.636002	0.557753	0.035*
C5	0.63166 (16)	0.49751 (10)	0.8740 (2)	0.0236 (4)
C6	0.71997 (18)	0.54982 (10)	1.2175 (2)	0.0284 (4)
H6A	0.746134	0.594707	1.170536	0.034*
H6B	0.636015	0.556435	1.221253	0.034*
C7	0.80161 (19)	0.53402 (11)	1.4016 (2)	0.0318 (4)
H7A	0.774890	0.488545	1.445197	0.038*
H7B	0.884609	0.526391	1.394499	0.038*
C8	0.80273 (18)	0.59419 (11)	1.5335 (2)	0.0318 (4)
H8A	0.720371	0.600857	1.544146	0.038*
H8B	0.827396	0.640071	1.488945	0.038*
C9	0.88802 (19)	0.57782 (12)	1.7150 (2)	0.0348 (5)
H9A	0.864291	0.531126	1.756945	0.042*
H9B	0.970303	0.571941	1.703476	0.042*
C10	0.8907 (2)	0.63547 (11)	1.8535 (2)	0.0351 (5)
H10A	0.809207	0.640256	1.868614	0.042*
H10B	0.912217	0.682544	1.810629	0.042*
C11	0.97951 (19)	0.61888 (12)	2.0320 (2)	0.0349 (5)
H11A	0.956543	0.572383	2.075870	0.042*
H11B	1.060468	0.612554	2.015773	0.042*
C12	0.9864 (2)	0.67654 (12)	2.1710 (3)	0.0391 (5)
H12A	0.905293	0.683647	2.185985	0.047*
H12B	1.011361	0.722853	2.128801	0.047*
C13	1.0734 (2)	0.65819 (14)	2.3487 (3)	0.0470 (6)
H13A	1.153265	0.648814	2.334234	0.056*
H13B	1.045122	0.614956	2.396874	0.056*
H13C	1.078151	0.698927	2.429976	0.056*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ni1	0.02940 (18)	0.01765 (16)	0.01852 (16)	0.00189 (14)	0.00771 (13)	−0.00255 (13)
S1	0.0423 (3)	0.0221 (2)	0.0226 (2)	0.0069 (2)	0.0055 (2)	−0.00327 (19)
S2	0.0348 (3)	0.0295 (2)	0.0225 (2)	0.0061 (2)	0.0041 (2)	−0.0013 (2)
N1	0.0317 (9)	0.0195 (7)	0.0187 (7)	0.0016 (6)	0.0066 (6)	−0.0007 (6)
N2	0.0314 (9)	0.0245 (8)	0.0193 (7)	0.0011 (6)	0.0050 (6)	−0.0028 (6)
C1	0.0578 (15)	0.0326 (11)	0.0314 (11)	0.0130 (10)	0.0134 (10)	−0.0055 (9)
C2	0.0600 (15)	0.0315 (11)	0.0382 (11)	0.0013 (10)	0.0159 (11)	−0.0078 (9)
C3	0.0490 (13)	0.0223 (9)	0.0220 (9)	0.0080 (9)	0.0091 (9)	−0.0031 (8)
C4	0.0434 (12)	0.0243 (9)	0.0203 (9)	0.0065 (8)	0.0080 (8)	0.0005 (8)
C5	0.0276 (9)	0.0232 (8)	0.0209 (8)	−0.0011 (8)	0.0082 (7)	−0.0016 (8)
C6	0.0313 (11)	0.0297 (10)	0.0244 (9)	0.0006 (8)	0.0083 (8)	−0.0027 (8)
C7	0.0351 (11)	0.0349 (11)	0.0234 (9)	0.0026 (9)	0.0051 (8)	−0.0035 (9)
C8	0.0354 (11)	0.0355 (10)	0.0236 (9)	−0.0011 (9)	0.0069 (8)	−0.0033 (9)
C9	0.0363 (11)	0.0414 (12)	0.0245 (9)	0.0019 (9)	0.0053 (8)	−0.0037 (9)
C10	0.0434 (13)	0.0330 (11)	0.0278 (10)	−0.0023 (9)	0.0082 (9)	−0.0041 (9)
C11	0.0360 (12)	0.0395 (11)	0.0281 (10)	−0.0012 (9)	0.0073 (9)	−0.0083 (9)
C12	0.0469 (13)	0.0388 (12)	0.0314 (10)	−0.0079 (10)	0.0110 (9)	−0.0087 (9)
C13	0.0447 (14)	0.0614 (15)	0.0323 (11)	−0.0070 (11)	0.0069 (10)	−0.0129 (11)

Geometric parameters (Å, º) top

Ni1—N1	1.9193 (14)	C6—H6B	0.9900
Ni1—N1ⁱ	1.9193 (14)	C7—C8	1.520 (3)
Ni1—S1ⁱ	2.1788 (5)	C7—H7A	0.9900
Ni1—S1	2.1788 (5)	C7—H7B	0.9900
S1—C5	1.7295 (18)	C8—C9	1.522 (3)
S2—C5	1.7416 (18)	C8—H8A	0.9900
S2—C6	1.8138 (19)	C8—H8B	0.9900
N1—C4	1.288 (2)	C9—C10	1.520 (3)
N1—N2	1.420 (2)	C9—H9A	0.9900
N2—C5	1.290 (2)	C9—H9B	0.9900
C1—C3	1.526 (3)	C10—C11	1.521 (3)
C1—H1A	0.9800	C10—H10A	0.9900
C1—H1B	0.9800	C10—H10B	0.9900
C1—H1C	0.9800	C11—C12	1.514 (3)
C2—C3	1.530 (3)	C11—H11A	0.9900
C2—H2A	0.9800	C11—H11B	0.9900
C2—H2B	0.9800	C12—C13	1.516 (3)
C2—H2C	0.9800	C12—H12A	0.9900
C3—C4	1.496 (2)	C12—H12B	0.9900
C3—H3	1.0000	C13—H13A	0.9800
C4—H4	0.9500	C13—H13B	0.9800
C6—C7	1.521 (2)	C13—H13C	0.9800
C6—H6A	0.9900

N1—Ni1—N1ⁱ	180.0	C8—C7—C6	113.37 (16)
N1—Ni1—S1ⁱ	93.95 (4)	C8—C7—H7A	108.9
N1ⁱ—Ni1—S1ⁱ	86.05 (4)	C6—C7—H7A	108.9
N1—Ni1—S1	86.05 (4)	C8—C7—H7B	108.9
N1ⁱ—Ni1—S1	93.95 (4)	C6—C7—H7B	108.9
S1ⁱ—Ni1—S1	180.00 (2)	H7A—C7—H7B	107.7
C5—S1—Ni1	95.74 (6)	C7—C8—C9	112.13 (16)
C5—S2—C6	103.11 (8)	C7—C8—H8A	109.2
C4—N1—N2	111.92 (14)	C9—C8—H8A	109.2
C4—N1—Ni1	127.63 (13)	C7—C8—H8B	109.2
N2—N1—Ni1	120.45 (11)	C9—C8—H8B	109.2
C5—N2—N1	111.59 (14)	H8A—C8—H8B	107.9
C3—C1—H1A	109.5	C10—C9—C8	114.43 (17)
C3—C1—H1B	109.5	C10—C9—H9A	108.7
H1A—C1—H1B	109.5	C8—C9—H9A	108.7
C3—C1—H1C	109.5	C10—C9—H9B	108.7
H1A—C1—H1C	109.5	C8—C9—H9B	108.7
H1B—C1—H1C	109.5	H9A—C9—H9B	107.6
C3—C2—H2A	109.5	C9—C10—C11	113.32 (17)
C3—C2—H2B	109.5	C9—C10—H10A	108.9
H2A—C2—H2B	109.5	C11—C10—H10A	108.9
C3—C2—H2C	109.5	C9—C10—H10B	108.9
H2A—C2—H2C	109.5	C11—C10—H10B	108.9
H2B—C2—H2C	109.5	H10A—C10—H10B	107.7
C4—C3—C1	110.15 (16)	C12—C11—C10	114.35 (17)
C4—C3—C2	109.32 (17)	C12—C11—H11A	108.7
C1—C3—C2	111.16 (17)	C10—C11—H11A	108.7
C4—C3—H3	108.7	C12—C11—H11B	108.7
C1—C3—H3	108.7	C10—C11—H11B	108.7
C2—C3—H3	108.7	H11A—C11—H11B	107.6
N1—C4—C3	127.07 (17)	C11—C12—C13	113.45 (18)
N1—C4—H4	116.5	C11—C12—H12A	108.9
C3—C4—H4	116.5	C13—C12—H12A	108.9
N2—C5—S1	124.84 (14)	C11—C12—H12B	108.9
N2—C5—S2	119.66 (13)	C13—C12—H12B	108.9
S1—C5—S2	115.50 (10)	H12A—C12—H12B	107.7
C7—C6—S2	107.68 (13)	C12—C13—H13A	109.5
C7—C6—H6A	110.2	C12—C13—H13B	109.5
S2—C6—H6A	110.2	H13A—C13—H13B	109.5
C7—C6—H6B	110.2	C12—C13—H13C	109.5
S2—C6—H6B	110.2	H13A—C13—H13C	109.5
H6A—C6—H6B	108.5	H13B—C13—H13C	109.5

C4—N1—N2—C5	169.13 (17)	C6—S2—C5—N2	5.12 (18)
Ni1—N1—N2—C5	−10.2 (2)	C6—S2—C5—S1	−174.45 (11)
N2—N1—C4—C3	1.5 (3)	C5—S2—C6—C7	179.27 (14)
Ni1—N1—C4—C3	−179.19 (15)	S2—C6—C7—C8	179.81 (15)
C1—C3—C4—N1	−154.1 (2)	C6—C7—C8—C9	−178.30 (18)
C2—C3—C4—N1	83.5 (2)	C7—C8—C9—C10	−178.72 (18)
N1—N2—C5—S1	1.2 (2)	C8—C9—C10—C11	−178.20 (19)
N1—N2—C5—S2	−178.29 (12)	C9—C10—C11—C12	178.39 (19)
Ni1—S1—C5—N2	6.18 (17)	C10—C11—C12—C13	178.8 (2)
Ni1—S1—C5—S2	−174.28 (9)

Symmetry code: (i) −x+1, −y+1, −z+1.

Comparative geometrical parameters (Å, °) for bis-chelated Ni complexes with dithiocarbazato ligands bearing an S-octyl/S-hexyl (n) alkyl chain top

Complex	CSD Refcode	n	Ni—N	Ni—S	N—Ni—S
This work	–	8	1.9193 (14)	2.1788 (5)	86.05 (4)
1	BIQTIH	8	1.9310 (19)	2.1796 (6)	85.67 (5)
2	MIMTIG	8	1.9168 (19)	2.1735 (7)	85.88 (6)
3, ligand 1	QIVYUT	8	1.9318 (16)	2.1506 (6)	86.26 (5)
3, ligand 2	QIVYUT	8	1.9392 (16)	2.1573 (6)	86.40 (5)
4	LUBYAK	6	1.933 (3)	2.1775 (10)	86.04 (9)
5, ligand 1	JUYCAJ	6	1.9112 (12)	2.1785 (4)	85.74 (3)
5, ligand 2	JUYCAJ	6	1.9177 (12)	2.1812 (4)	86.03 (4)
6	WEGKEB	6	1.915 (2)	2.1788 (8)	85.58 (8)
7	TILVUJ	6	1.9295 (10)	2.1600 (4)	85.68 (3)

Notes: Complex 1 (Begum et al., 2018); 2 (Kahn et al., 2023a); 3 (Kahn et al., 2023b); 4 (Howlader et al., 2015); 5 (Begum et al., 2016); 6 (Begum et al., 2017); 7 (Begum et al., 2020). Complexes 3 and 7 show a cis configuration of ligands.

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 Toyama, for providing facilities for single-crystal X-ray analyses.

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