Bis[S-octyl 3-(4-meth­oxy­benzyl­idene)di­thio­carbazato-κ2N3,S]nickel(II)

Begum, K.; Zangrando, E.; Begum, M.S.; Sheikh, M.C.; Miyatake, R.

doi:10.1107/S241431461801684X

metal-organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 3| Part 12| December 2018| x181684

https://doi.org/10.1107/S241431461801684X

Open

access

Bis[S-octyl 3-(4-methoxybenzylidene)dithiocarbazato-κ²N³,S]nickel(II)

Khurshida Begum,^a ^* Ennio Zangrando,^b M. Sabina Begum,^c Md. Chanmiya Sheikh ^d and Ryuta Miyatake ^e

^aDepartment of Physics, Shahjalal University of Science and Technology, Sylhet-3114, Bangladesh, ^bDepartment of Chemical and Pharmaceutical Sciences, via Giorgieri 1, 34127, Trieste, Italy, ^cDepartment of Chemistry, Shahjalal University of Science and Technology, Sylhet-3114, Bangladesh, ^dDepartment of Applied Chemistry, Faculty of Engineering, University of Toyama, 3190 Gofuku, Toyama, 930-8555, Japan, and ^eCenter for Environmental Conservation and Research Safety, University of Toyama, 3190 Gofuku, Toyama, 930-8555, Japan
^*Correspondence e-mail: china@sust.edu

Edited by H. Stoeckli-Evans, University of Neuchâtel, Switzerland (Received 18 November 2018; accepted 26 November 2018; online 5 December 2018)

The nickel(II) cation of the title complex, [Ni(C₁₇H₂₅N₂OS₂)₂], is located on a crystallographic inversion centre. It has a square-planar coordination geometry, with a trans configuration of the N,S-chelating ligands, as imposed by the crystal symmetry.

Keywords: crystal structure; nickel(II) complex; dithiocarbazate ligand; alkyl chain.

CCDC reference: 1057810

Structure description

Bidentate Schiff bases of S-methyl or S-benzyl dithiocarbazates and their metal complexes have received considerable attention for their possible bioactivities. As part of our ongoing structural studies of S-containing Schiff bases (Howlader et al., 2015 ; Islam et al., 2011 , 2014 ), we now report on the structure of the title complex in which the ligand has a long alkyl chain.

The molecular structure of the title complex is illustrated in Fig. 1. The complex has the nickel(II) cation located on a crystallographic inversion centre with the two Schiff bases, in their deprotonated imino thiolate form, chelating through the azomethine nitrogen atom N1 and the thiolate sulfur atom S1 in a trans-planar configuration, as imposed by the crystal symmetry. The complex has a coplanar geometry with the exception of the octyl chains that extend above and below the coordination plane (Fig. 1). The Ni—S and Ni—N bond lengths are 2.1796 (6) and 1.9310 (19) Å, respectively, and the S1—Ni1—N1 chelating angle is 85.67 (5)°. These geometrical parameters are comparable to those found in the related bis-chelated nickel(II) complex with the S-hexyl 3-(4-methylbenzylidene)dithiocarbazate ligand (Howlader et al., 2015). There the corresponding bond lengths and angles are 2.1775 (10) and 1.933 (3) Å, and 86.04 (9)°, respectively, indicating that neither the longer alkyl group nor the different Schiff base affects the coordination bond lengths.

Figure 1
A view of the molecular structure of the title complex, with the atom labelling. Displacement ellipsoids are drawn at the 50% probability level. Symmetry code (i) −x + 1, −y + 1, −z + 1.

The structure of the title ligand (HL), reported by Begum et al. (2015 ), shows that on coordination, a 180° rotation occurs about the C9—N2 bond in order to allow N,S chelation to the metal atom. Upon coordination, some salient features are also observed with respect to the free ligand. The most significant is an elongation of the C9—S1 bond length from 1.6734 (15) Å in the ligand to 1.7514 (19) Å in the title complex, thus validating the coordination with the deprotonated thiolate sulfur atom. Correspondingly, the N2—C9 bond length of 1.3343 (16) Å in HL is shortened to 1.285 (3) Å in the title complex, while the N1—N2 bond length of 1.3829 (17) Å in HL is slightly elongated to 1.413 (3) Å in the complex. These geometrical parameters agree with those reported for similar nickel complexes when the ligands assume either a trans (Islam et al., 2011, 2014; Zhang et al., 2004 ) or a cis configuration (Chan et al., 2008 ; Li et al., 2006 ).

In the crystal, complex molecules stack up the a axis at a distance of 4.55302 (14) Å, thus excluding any significant interactions between the aromatic rings (see Fig. 2).

Figure 2
A view approximately along the b axis of the crystal packing of the title complex.

Synthesis and crystallization

A solution of Ni(CH₃COO)₂·4H₂O (0.06 g, 0.25 mmol) in methanol (7 ml) was added to a methanol solution (10 ml) of the S-octyl (E)-3-(4-methoxybenzylidene)dithiocarbazate ligand (0.17 g, 0.5 mmol). The resulting mixture was stirred at room temperature for 5 h. The dark orange precipitate that formed was filtered off, washed with methanol and dried in vacuo over anhydrous CaCl₂. Dark orange single crystals of the title complex (m.p. 371 K), suitable for X-ray diffraction analysis, were obtained by slow evaporation from a mixture of chloroform/toluene (6:1 v:v).

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 1.

Table 1
Experimental details

Crystal data
Chemical formula	[Ni(C₁₇H₂₅N₂OS₂)₂]
M_r	733.73
Crystal system, space group	Triclinic, P $[\overline{1}]$
Temperature (K)	173
a, b, c (Å)	4.55302 (14), 11.5641 (3), 17.5075 (5)
α, β, γ (°)	84.1436 (7), 85.6165 (10), 76.4084 (10)
V (Å³)	890.00 (5)
Z	1
Radiation type	Mo Kα
μ (mm⁻¹)	0.82
Crystal size (mm)	0.27 × 0.12 × 0.07

Data collection
Diffractometer	Rigaku R-AXIS RAPID
Absorption correction	Multi-scan (ABSCOR; Higashi, 1995 )
T_min, T_max	0.866, 0.944
No. of measured, independent and observed [F² > 2.0σ(F²)] reflections	8899, 4041, 3705
R_int	0.025
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.039, 0.112, 1.15
No. of reflections	4041
No. of parameters	207
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.17, −0.37
Computer programs: RAPID-AUTO (Rigaku, 1999 ), SIR92 (Altomare et al., 1994 ), SHELXL97 (Sheldrick, 2008 ) and CrystalStructure (Rigaku, 2010 ).

Structural data

CCDC reference: 1057810

Crystal structure: contains datablocks General, I. DOI: https://doi.org/10.1107/S241431461801684X/su4168sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S241431461801684X/su4168Isup2.hkl

checkCIF report

Computing details top

Data collection: RAPID-AUTO (Rigaku, 1999); cell refinement: RAPID-AUTO (Rigaku, 1999); data reduction: RAPID-AUTO (Rigaku, 1999); 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).

Bis[S-octyl 3-(4-methoxybenzylidene)dithiocarbazato-\ κ²N³,S]nickel(II) top

Crystal data top

[Ni(C₁₇H₂₅N₂OS₂)₂]	Z = 1
M_r = 733.73	F(000) = 390.00
Triclinic, P1	D_x = 1.369 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71075 Å
a = 4.55302 (14) Å	Cell parameters from 8264 reflections
b = 11.5641 (3) Å	θ = 3.1–27.5°
c = 17.5075 (5) Å	µ = 0.82 mm⁻¹
α = 84.1436 (7)°	T = 173 K
β = 85.6165 (10)°	Platelet, orange
γ = 76.4084 (10)°	0.27 × 0.12 × 0.07 mm
V = 890.00 (5) Å³

Data collection top

Rigaku R-AXIS RAPID diffractometer	3705 reflections with F² > 2.0σ(F²)
Detector resolution: 10.000 pixels mm^-1	R_int = 0.025
ω scans	θ_max = 27.5°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −5→5
T_min = 0.866, T_max = 0.944	k = −14→14
8899 measured reflections	l = −22→21
4041 independent reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.112	H-atom parameters constrained
S = 1.15	w = 1/[σ²(F_o²) + (0.0566P)² + 0.5813P] where P = (F_o² + 2F_c²)/3
4041 reflections	(Δ/σ)_max = 0.001
207 parameters	Δρ_max = 1.17 e Å⁻³
0 restraints	Δρ_min = −0.37 e Å⁻³
Primary atom site location: structure-invariant direct methods

Special details top

Geometry. ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY

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 sigma(F²) is used only for calculating R-factor (gt).

The H atoms were located geometrically and treated as riding atoms: C—H = 0.95–0.99 Å with U_iso(H) = 1.5U_eq(C-methyl) and 1.2U_eq(C) for other H atoms.

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

	x	y	z	U_iso*/U_eq
Ni	0.5000	0.5000	0.5000	0.02291 (12)
S1	0.53959 (14)	0.35043 (5)	0.58802 (3)	0.03236 (15)
S2	0.72806 (13)	0.33241 (4)	0.74527 (3)	0.02987 (14)
O1	1.3002 (4)	0.96865 (14)	0.71096 (9)	0.0387 (4)
N1	0.6922 (4)	0.57294 (15)	0.57058 (9)	0.0247 (4)
N2	0.7284 (4)	0.52311 (15)	0.64734 (9)	0.0256 (4)
C1	0.9372 (5)	0.73725 (17)	0.59923 (11)	0.0249 (4)
C2	1.0441 (5)	0.82953 (18)	0.55700 (12)	0.0292 (5)
C3	1.1693 (5)	0.90850 (18)	0.59111 (12)	0.0302 (5)
C4	1.1880 (5)	0.89570 (18)	0.67074 (12)	0.0283 (4)
C5	1.0869 (6)	0.8034 (2)	0.71388 (13)	0.0353 (5)
C6	0.9640 (6)	0.72470 (19)	0.67942 (12)	0.0314 (5)
C7	1.3781 (6)	1.0717 (2)	0.66998 (15)	0.0397 (6)
C8	0.8008 (5)	0.66685 (18)	0.55359 (11)	0.0264 (4)
C9	0.6696 (5)	0.41906 (17)	0.65734 (11)	0.0243 (4)
C10	0.8698 (5)	0.42720 (18)	0.80277 (11)	0.0282 (4)
C11	0.6211 (5)	0.51742 (19)	0.84182 (12)	0.0291 (4)
C12	0.7464 (5)	0.58919 (19)	0.89491 (12)	0.0293 (5)
C13	0.5011 (5)	0.6716 (2)	0.94072 (12)	0.0314 (5)
C14	0.6261 (5)	0.73863 (19)	0.99649 (12)	0.0306 (5)
C15	0.3830 (5)	0.82086 (19)	1.04283 (12)	0.0305 (5)
C16	0.5078 (6)	0.8927 (2)	1.09547 (13)	0.0335 (5)
C17	0.2620 (6)	0.9785 (2)	1.13894 (14)	0.0418 (6)
H1	1.0306	0.8386	0.5028	0.0351*
H2	1.2411	0.9701	0.5608	0.0362*
H3	1.1027	0.7943	0.7681	0.0423*
H4	0.8974	0.6620	0.7099	0.0377*
H5	1.5416	1.0465	0.6312	0.0476*
H6	1.4452	1.1184	0.7060	0.0476*
H7	1.2007	1.1208	0.6446	0.0476*
H8	0.7894	0.6958	0.5009	0.0316*
H9	0.9957	0.3763	0.8426	0.0338*
H10	1.0013	0.4706	0.7693	0.0338*
H11	0.4799	0.4749	0.8721	0.0349*
H12	0.5055	0.5730	0.8021	0.0349*
H13	0.8793	0.5331	0.9312	0.0352*
H14	0.8718	0.6376	0.8636	0.0352*
H15	0.3694	0.6238	0.9700	0.0377*
H16	0.3744	0.7304	0.9045	0.0377*
H17	0.7537	0.6798	1.0325	0.0367*
H18	0.7571	0.7866	0.9671	0.0367*
H19	0.2587	0.7722	1.0744	0.0366*
H20	0.2485	0.8769	1.0069	0.0366*
H21	0.6347	0.8368	1.1330	0.0402*
H22	0.6391	0.9388	1.0643	0.0402*
H23	0.1296	1.0319	1.1022	0.0501*
H24	0.3557	1.0259	1.1689	0.0501*
H25	0.1426	0.9331	1.1737	0.0501*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ni	0.0282 (2)	0.02338 (19)	0.02004 (18)	−0.01005 (13)	−0.00419 (13)	−0.00357 (13)
S1	0.0511 (4)	0.0275 (3)	0.0245 (3)	−0.0186 (3)	−0.0109 (2)	−0.00139 (19)
S2	0.0432 (3)	0.0257 (3)	0.0235 (3)	−0.0124 (2)	−0.0073 (2)	−0.00067 (18)
O1	0.0545 (11)	0.0323 (8)	0.0371 (9)	−0.0207 (7)	−0.0132 (8)	−0.0064 (7)
N1	0.0302 (9)	0.0249 (8)	0.0207 (8)	−0.0086 (7)	−0.0036 (7)	−0.0027 (6)
N2	0.0322 (9)	0.0259 (8)	0.0206 (8)	−0.0089 (7)	−0.0047 (7)	−0.0030 (6)
C1	0.0266 (10)	0.0241 (9)	0.0258 (10)	−0.0070 (7)	−0.0046 (7)	−0.0053 (7)
C2	0.0362 (11)	0.0285 (10)	0.0250 (10)	−0.0103 (8)	−0.0045 (8)	−0.0035 (8)
C3	0.0355 (11)	0.0258 (10)	0.0318 (11)	−0.0118 (8)	−0.0018 (9)	−0.0034 (8)
C4	0.0287 (10)	0.0251 (9)	0.0335 (11)	−0.0070 (8)	−0.0077 (8)	−0.0075 (8)
C5	0.0517 (14)	0.0316 (11)	0.0266 (10)	−0.0142 (10)	−0.0113 (10)	−0.0037 (8)
C6	0.0444 (13)	0.0281 (10)	0.0256 (10)	−0.0148 (9)	−0.0067 (9)	−0.0015 (8)
C7	0.0493 (14)	0.0314 (11)	0.0456 (14)	−0.0196 (10)	−0.0076 (11)	−0.0095 (10)
C8	0.0305 (10)	0.0280 (10)	0.0227 (9)	−0.0097 (8)	−0.0047 (8)	−0.0032 (7)
C9	0.0258 (10)	0.0268 (10)	0.0211 (9)	−0.0056 (7)	−0.0027 (7)	−0.0050 (7)
C10	0.0336 (11)	0.0297 (10)	0.0235 (10)	−0.0096 (8)	−0.0085 (8)	−0.0024 (8)
C11	0.0310 (11)	0.0335 (11)	0.0261 (10)	−0.0119 (8)	−0.0043 (8)	−0.0060 (8)
C12	0.0304 (11)	0.0364 (11)	0.0251 (10)	−0.0133 (9)	−0.0042 (8)	−0.0059 (8)
C13	0.0309 (11)	0.0374 (11)	0.0291 (10)	−0.0108 (9)	−0.0048 (8)	−0.0083 (9)
C14	0.0330 (11)	0.0353 (11)	0.0272 (10)	−0.0130 (9)	−0.0047 (8)	−0.0057 (8)
C15	0.0350 (11)	0.0316 (10)	0.0277 (10)	−0.0118 (9)	−0.0050 (8)	−0.0041 (8)
C16	0.0396 (12)	0.0345 (11)	0.0300 (11)	−0.0125 (9)	−0.0078 (9)	−0.0057 (9)
C17	0.0534 (15)	0.0356 (12)	0.0375 (13)	−0.0065 (11)	−0.0114 (11)	−0.0104 (10)

Geometric parameters (Å, º) top

Ni—S1	2.1796 (6)	C2—H1	0.950
Ni—S1ⁱ	2.1796 (6)	C3—H2	0.950
Ni—N1	1.9310 (19)	C5—H3	0.950
Ni—N1ⁱ	1.9310 (19)	C6—H4	0.950
S1—C9	1.726 (3)	C7—H5	0.980
S2—C9	1.7514 (19)	C7—H6	0.980
S2—C10	1.813 (3)	C7—H7	0.980
O1—C4	1.359 (3)	C8—H8	0.950
O1—C7	1.430 (3)	C10—H9	0.990
N1—N2	1.413 (3)	C10—H10	0.990
N1—C8	1.295 (3)	C11—H11	0.990
N2—C9	1.285 (3)	C11—H12	0.990
C1—C2	1.397 (3)	C12—H13	0.990
C1—C6	1.408 (3)	C12—H14	0.990
C1—C8	1.461 (4)	C13—H15	0.990
C2—C3	1.387 (4)	C13—H16	0.990
C3—C4	1.394 (3)	C14—H17	0.990
C4—C5	1.391 (4)	C14—H18	0.990
C5—C6	1.381 (4)	C15—H19	0.990
C10—C11	1.520 (3)	C15—H20	0.990
C11—C12	1.530 (4)	C16—H21	0.990
C12—C13	1.523 (3)	C16—H22	0.990
C13—C14	1.524 (4)	C17—H23	0.980
C14—C15	1.521 (3)	C17—H24	0.980
C15—C16	1.523 (4)	C17—H25	0.980
C16—C17	1.523 (4)

S1—Ni—S1ⁱ	180	H5—C7—H7	109.469
S1—Ni—N1	85.67 (5)	H6—C7—H7	109.468
S1—Ni—N1ⁱ	94.33 (5)	N1—C8—H8	113.566
S1ⁱ—Ni—N1	94.33 (5)	C1—C8—H8	113.564
S1ⁱ—Ni—N1ⁱ	85.67 (5)	S2—C10—H9	108.878
N1—Ni—N1ⁱ	180	S2—C10—H10	108.867
Ni—S1—C9	96.01 (7)	C11—C10—H9	108.875
C9—S2—C10	102.83 (10)	C11—C10—H10	108.870
C4—O1—C7	117.90 (18)	H9—C10—H10	107.715
Ni—N1—N2	120.42 (14)	C10—C11—H11	109.150
Ni—N1—C8	125.18 (14)	C10—C11—H12	109.154
N2—N1—C8	114.39 (18)	C12—C11—H11	109.156
N1—N2—C9	111.78 (18)	C12—C11—H12	109.148
C2—C1—C6	117.6 (2)	H11—C11—H12	107.871
C2—C1—C8	114.61 (18)	C11—C12—H13	108.897
C6—C1—C8	127.8 (2)	C11—C12—H14	108.908
C1—C2—C3	122.6 (2)	C13—C12—H13	108.898
C2—C3—C4	118.7 (2)	C13—C12—H14	108.904
O1—C4—C3	124.3 (2)	H13—C12—H14	107.731
O1—C4—C5	116.1 (2)	C12—C13—H15	108.904
C3—C4—C5	119.7 (3)	C12—C13—H16	108.898
C4—C5—C6	121.2 (2)	C14—C13—H15	108.903
C1—C6—C5	120.2 (2)	C14—C13—H16	108.909
N1—C8—C1	132.87 (18)	H15—C13—H16	107.731
S1—C9—S2	114.13 (12)	C13—C14—H17	108.794
S1—C9—N2	124.92 (15)	C13—C14—H18	108.791
S2—C9—N2	120.93 (17)	C15—C14—H17	108.796
S2—C10—C11	113.48 (16)	C15—C14—H18	108.799
C10—C11—C12	112.26 (18)	H17—C14—H18	107.675
C11—C12—C13	113.35 (18)	C14—C15—H19	108.797
C12—C13—C14	113.35 (19)	C14—C15—H20	108.794
C13—C14—C15	113.81 (19)	C16—C15—H19	108.799
C14—C15—C16	113.81 (19)	C16—C15—H20	108.804
C15—C16—C17	113.3 (2)	H19—C15—H20	107.669
C1—C2—H1	118.691	C15—C16—H21	108.921
C3—C2—H1	118.690	C15—C16—H22	108.918
C2—C3—H2	120.632	C17—C16—H21	108.926
C4—C3—H2	120.627	C17—C16—H22	108.913
C4—C5—H3	119.383	H21—C16—H22	107.738
C6—C5—H3	119.378	C16—C17—H23	109.473
C1—C6—H4	119.926	C16—C17—H24	109.467
C5—C6—H4	119.914	C16—C17—H25	109.462
O1—C7—H5	109.474	H23—C17—H24	109.479
O1—C7—H6	109.474	H23—C17—H25	109.474
O1—C7—H7	109.472	H24—C17—H25	109.472
H5—C7—H6	109.470

S1—Ni—N1—N2	−11.14 (10)	C8—N1—N2—C9	−167.88 (15)
S1—Ni—N1—C8	167.80 (12)	N1—N2—C9—S1	−3.7 (3)
N1—Ni—S1—C9	6.77 (5)	N1—N2—C9—S2	174.53 (13)
S1—Ni—N1ⁱ—N2ⁱ	−168.86 (10)	C2—C1—C6—C5	1.2 (3)
S1—Ni—N1ⁱ—C8ⁱ	12.20 (12)	C6—C1—C2—C3	−0.9 (3)
N1ⁱ—Ni—S1—C9	−173.23 (5)	C2—C1—C8—N1	176.14 (18)
S1ⁱ—Ni—N1—N2	168.86 (10)	C8—C1—C2—C3	177.33 (15)
S1ⁱ—Ni—N1—C8	−12.20 (12)	C6—C1—C8—N1	−5.8 (4)
N1—Ni—S1ⁱ—C9ⁱ	173.23 (5)	C8—C1—C6—C5	−176.73 (17)
S1ⁱ—Ni—N1ⁱ—N2ⁱ	11.14 (10)	C1—C2—C3—C4	−0.3 (3)
S1ⁱ—Ni—N1ⁱ—C8ⁱ	−167.80 (12)	C2—C3—C4—O1	−178.68 (17)
N1ⁱ—Ni—S1ⁱ—C9ⁱ	−6.77 (5)	C2—C3—C4—C5	1.2 (3)
Ni—S1—C9—S2	177.99 (9)	O1—C4—C5—C6	179.01 (17)
Ni—S1—C9—N2	−3.64 (16)	C3—C4—C5—C6	−0.9 (3)
C9—S2—C10—C11	84.61 (13)	C4—C5—C6—C1	−0.4 (3)
C10—S2—C9—S1	178.65 (11)	S2—C10—C11—C12	175.43 (11)
C10—S2—C9—N2	0.21 (17)	C10—C11—C12—C13	−174.38 (15)
C7—O1—C4—C3	6.1 (3)	C11—C12—C13—C14	177.19 (15)
C7—O1—C4—C5	−173.77 (16)	C12—C13—C14—C15	−179.74 (15)
Ni—N1—N2—C9	11.17 (19)	C13—C14—C15—C16	−176.95 (15)
Ni—N1—C8—C1	176.31 (13)	C14—C15—C16—C17	177.52 (15)
N2—N1—C8—C1	−4.7 (3)

Symmetry code: (i) −x+1, −y+1, −z+1.

Acknowledgements

KB and MSB are grateful to the Department of Chemistry, Shahjalal University of Science and Technology, Sylhet-3114, for the provision of laboratory facilities.

Funding information

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
Begum, M. S., Zangrando, E., Sheikh, M. C., Miyatake, R. & Hossain, M. M. (2015). Acta Cryst. E71, o265–o266. Web of Science CrossRef IUCr Journals Google Scholar
Chan, M. E., Crouse, K. A., Tahir, M. I. M., Rosli, R., Umar-Tsafe, N. & Cowley, A. R. (2008). Polyhedron, 27, 1141–1149. Web of Science CrossRef CAS Google Scholar
Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan. Google Scholar
Howlader, M. B. H., Begum, M. S., Sheikh, M. C., Miyatake, R. & Zangrando, E. (2015). Acta Cryst. E71, m26–m27. CrossRef IUCr Journals Google Scholar
Islam, M. A. A. A. A., Sheikh, M. C., Alam, M. S., Zangrando, E., Alam, M. A., Tarafder, M. T. H. & Miyatake, R. (2014). Transition Met. Chem. 39, 141–149. Web of Science CrossRef CAS Google Scholar
Islam, M. A. A. A. A., Tarafder, M. T. H., Sheikh, M. C., Alam, M. A. & Zangrando, E. (2011). Transition Met. Chem. 36, 531–537. CrossRef Google Scholar
Li, S.-L., Wu, J.-Y., Tian, Y.-P., Tang, Y.-W., Jiang, M.-H., Fun, H. K. & Chantrapromma, S. (2006). Opt. Mater. 28, 897–903. CrossRef Google Scholar
Rigaku (1999). RAPID AUTO. Rigaku Corporation, Tokyo, Japan. Google Scholar
Rigaku (2010). CrystalStructure. Rigaku Corporation, Tokyo, Japan. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Zhang, M.-L., Tian, Y.-P., Zhang, X.-J., Wu, J.-Y., Zhang, S.-Y., Wang, D., Jiang, M.-H., Chantrapromm, S. & Fun, H. K. (2004). Transition Met. Chem. 29, 596–602. CrossRef Google Scholar