Di­chlorido­{N,N,N′-trimethyl-N′-(1H-pyrazol-1-yl-κN2)meth­yl]ethane-1,2-di­amine-κ2N,N′}copper(II) methanol monosolvate

Singh, R.; Ali, A.; Faizi, M.S.H.; Singh, R.; Iskenderov, T.S.; Dege, N.

doi:10.1107/S2414314619006928

metal-organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 4| Part 5| May 2019| x190692

https://doi.org/10.1107/S2414314619006928

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Dichlorido{N,N,N′-trimethyl-N′-(1H-pyrazol-1-yl-κN²)methyl]ethane-1,2-diamine-κ²N,N′}copper(II) methanol monosolvate

Ravindra Singh,^a Akram Ali,^b Md. Serajul Haque Faizi,^c Roona Singh,^a Turganbay S. Iskenderov ^d ^* and Necmi Dege ^e

^aDepartment of Chemistry, M.S.J. Govt. (PG) College Bharatpur, Bharatpur, Rajasthan 321001, India, ^bCMP College Allahabad, a constitution college of Allahabad University, Allahabad, Uttar Pradesh 211002, India, ^cDepartment of Chemistry, Langat Singh College, B.R.A. Bihar University, Muzaffarpur, Bihar 842001, India, ^dDepartment of Chemistry, Taras Shevchenko National University, Volodymyrska str., 64, 01601 Kyiv, Ukraine, and ^eOndokuz Mayıs University, Faculty of Arts and Sciences, Department of Physics, 55139 Kurupelit, Samsun, Turkey
^*Correspondence e-mail: tiskenderov@ukr.net

Edited by S. Bernès, Benemérita Universidad Autónoma de Puebla, México (Received 25 March 2019; accepted 14 May 2019; online 31 May 2019)

In the title compound, [CuCl₂(C₉H₁₈N₄)]·CH₃OH, the central Cu^II ion is coordinated by three N atoms from the pyrazole derivative ligand and two chloride co-ligands. The coordination geometry around the Cu^II ion is distorted trigonal–bipyramidal. In the crystal, the molecules are linked by C—H⋯O, C—H⋯Cl and O—H⋯Cl hydrogen bonds, forming a three-dimensional framework with the lattice solvent molecule.

Keywords: crystal structure; pyrazole; copper; methanol solvate; ethylenediamine.

CCDC reference: 1915926

Structure description

Rigid ligands including pyrazole are some of the most desirable ligands to biologists and bioinorganic chemists for specific functions, such as catalysis and fluxional behaviour (Zhang et al., 2009 ; Arroyo et al., 2000 ), and also in electrochemistry (Morin et al., 2011 ). Recently, there has been considerable interest in the use of multifunctional ligands containing substituted pyrazole groups because of their potential applications in catalysis, and their ability to form complexes that mimic structural and catalytic functions in metalloproteins (García-Antón et al., 2003 ; Mukherjee, 2000 ; Pal et al., 2005 ; Shaw et al., 2004 ). In particular, the research field dealing with copper complexes embraces a wide range of topics, such as metastasis development (Turski et al., 2009 ; Finney et al., 2009 ), anticancer activity, and other aspects of bioinorganic chemistry.

As part of our continuing interest in coordination chemistry (Kumar et al., 2018 , 2019 ; Faizi et al., 2014 , 2018 ), we report herein the synthesis and structure of the title complex, [Cu(C₉H₁₈N₄)Cl₂]·CH₄O. In this mononuclear copper(II) compound (Fig. 1), the CuCl₂ group is bonded to a tridentate ligand, N,N,N′-trimethyl-N′-pyrazol-1-ylmethyl-ethane-1,2-diamine (TPED), and the asymmetric unit is completed by a methanol solvate molecule. The central Cu^II ion is coordinated by the tridentate N-chelating TPED ligand and two Cl⁻ ions in a distorted trigonal–bipyramidal geometry, with the chloride ligands and the central ethylenediamine N atom (N3) occupying the equatorial positions [Cu—Cl = 2.4630 (15) and 2.2914 (15) Å; Cu—N = 2.125 (4) Å], while the coordinating pyrazole N atom and the terminal ethylenediamine N atom (N4) are placed in axial positions [Cu—N = 1.991 (4) and 2.043 (4) Å]. In the crystal, the molecules are linked by weak O—H⋯Cl, C—H⋯O and C—H⋯Cl hydrogen bonds, forming a three dimensional network (Table 1; Figs. 2 and 3).

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯Cl1ⁱ	0.93	2.98	3.841 (6)	156
C3—H3⋯O1ⁱⁱ	0.93	2.62	3.305 (7)	131
C4—H4A⋯Cl2ⁱⁱ	0.97	2.67	3.636 (5)	173
C4—H4B⋯Cl1ⁱⁱⁱ	0.97	2.94	3.902 (5)	170
C5—H5A⋯Cl2^iv	0.96	2.93	3.745 (5)	143
C7—H7A⋯O1^v	0.97	2.42	3.281 (6)	148
C7—H7B⋯Cl2^iv	0.97	2.83	3.632 (5)	140
C8—H8B⋯Cl1ⁱⁱⁱ	0.96	2.81	3.736 (5)	162
O1—H1O⋯Cl2	0.91 (2)	2.16 (3)	3.047 (4)	164 (7)
Symmetry codes: (i) -x+1, -y, -z+2; (ii) x+1, y, z; (iii) -x+1, -y+1, -z+2; (iv) -x+1, -y+1, -z+1; (v) x, y+1, z.

Figure 1
The asymmetric unit of the title compound, with displacement ellipsoids drawn at the 40% probability level. The intermolecular O—H⋯Cl hydrogen bond between the solvent molecule and the main complex is also shown.

Figure 2
Part of the crystal structure showing the formation of a one-dimensional structure involving the lattice solvent and the main complex. Hydrogen bonds are shown as dashed lines.

Figure 3
The crystal packing of the title compound, viewed along the a axis. Hydrogen bonds: molecules are linked by weak C—H⋯O, C—H⋯Cl and O—H⋯Cl interactions. See Table 1

for details.

Synthesis and crystallization

[Cu^II(TPED)Cl₂]·CH₃OH: To a solution of TPED (0.050 g, 0.27 mmol) in 5 ml of methanol, solid CuCl₂·2H₂O (0.046 g, 0.27 mmol) was added portionwise. The colour of the solution changed from light yellow to blue. The solution was stirred for 1 h at 298 K. The blue solid that formed was filtered and washed with a methanol/diethyl ether mixture (1:3 v/v). The resulting blue solid was recrystallized by diffusion of diethyl ether into a solution of the complex in methanol, and the crystals were dried in vacuo. Yield: 0.072 g, 70%. C₁₀H₂₂Cl₂CuN₄O: calculated C 34.44, H 6.36, N 16.06; found C 34.94, H 6.86, N 16.78. UV–Vis [λ_max, nm (∊, M⁻¹cm⁻¹ in methanol)]: 680 (310), 290 (8900), 235 (16 800).

Refinement

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

Table 2
Experimental details

Crystal data
Chemical formula	[CuCl₂(C₉H₁₈N₄)]·CH₄O
M_r	348.75
Crystal system, space group	Triclinic, P $[\overline{1}]$
Temperature (K)	296
a, b, c (Å)	7.240 (5), 9.260 (5), 11.649 (5)
α, β, γ (°)	87.438 (5), 78.987 (5), 81.887 (5)
V (Å³)	758.8 (7)
Z	2
Radiation type	Mo Kα
μ (mm⁻¹)	1.79
Crystal size (mm)	0.18 × 0.14 × 0.10

Data collection
Diffractometer	Bruker SMART APEX CCD area detector
Absorption correction	Multi-scan (SADABS; Bruker, 2007 )
T_min, T_max	0.281, 0.397
No. of measured, independent and observed [I > 2σ(I)] reflections	3864, 2599, 2169
R_int	0.029
(sin θ/λ)_max (Å⁻¹)	0.596

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.055, 0.158, 1.04
No. of reflections	2599
No. of parameters	168
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	1.53, −0.61
Computer programs: APEX2 and SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008 ), SHELXL2018 (Sheldrick, 2015 ), ORTEP-3 for Windows (Farrugia, 2012 ), DIAMOND (Brandenburg, 2006 ) and publCIF (Westrip, 2010 ).

Structural data

CCDC reference: 1915926

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2414314619006928/bh4046sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314619006928/bh4046Isup2.hkl

checkCIF report

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2018 (Sheldrick, 2015); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and DIAMOND (Brandenburg, 2006); software used to prepare material for publication: publCIF (Westrip, 2010).

Dichlorido{N,N,N'-trimethyl-N'-(1H-pyrazol-1-yl-κN²)methyl]ethane-1,2-diamine-κ²N,N'}copper(II) methanol monosolvate top

Crystal data top

[CuCl₂(C₉H₁₈N₄)]·CH₄O	Z = 2
M_r = 348.75	F(000) = 362
Triclinic, P1	D_x = 1.526 Mg m⁻³
a = 7.240 (5) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.260 (5) Å	Cell parameters from 2494 reflections
c = 11.649 (5) Å	θ = 2.7–24.6°
α = 87.438 (5)°	µ = 1.79 mm⁻¹
β = 78.987 (5)°	T = 296 K
γ = 81.887 (5)°	Prism, blue
V = 758.8 (7) Å³	0.18 × 0.14 × 0.10 mm

Data collection top

Bruker SMART APEX CCD area detector diffractometer	2599 independent reflections
Radiation source: fine-focus sealed tube	2169 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.029
phi and ω scans	θ_max = 25.1°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2007)	h = −8→7
T_min = 0.281, T_max = 0.397	k = −8→11
3864 measured reflections	l = −13→13

Refinement top

Refinement on F²	1 restraint
Least-squares matrix: full	Hydrogen site location: mixed
R[F² > 2σ(F²)] = 0.055	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.158	w = 1/[σ²(F_o²) + (0.1044P)²] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max < 0.001
2599 reflections	Δρ_max = 1.53 e Å⁻³
168 parameters	Δρ_min = −0.61 e Å⁻³

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

	x	y	z	U_iso*/U_eq
Cu1	0.45726 (7)	0.39934 (6)	0.79843 (4)	0.0189 (2)
Cl1	0.21622 (15)	0.35638 (12)	0.94918 (10)	0.0218 (3)
Cl2	0.34205 (16)	0.33139 (13)	0.62524 (10)	0.0254 (3)
O1	0.3144 (6)	0.0068 (4)	0.6629 (4)	0.0446 (10)
N1	0.6201 (5)	0.2174 (4)	0.8341 (3)	0.0221 (9)
N2	0.8060 (5)	0.2307 (4)	0.8190 (3)	0.0224 (9)
N3	0.7305 (5)	0.4460 (4)	0.7149 (3)	0.0198 (8)
N4	0.3760 (5)	0.6189 (4)	0.7857 (3)	0.0196 (8)
C1	0.6077 (7)	0.0801 (5)	0.8671 (4)	0.0269 (11)
H1	0.494998	0.039437	0.883402	0.032*
C2	0.7861 (7)	0.0041 (6)	0.8744 (5)	0.0309 (12)
H2	0.815459	−0.093094	0.896052	0.037*
C3	0.9082 (7)	0.1060 (5)	0.8423 (5)	0.0298 (12)
H3	1.039138	0.090345	0.837685	0.036*
C4	0.8589 (6)	0.3763 (5)	0.7913 (4)	0.0228 (10)
H4A	0.990186	0.370218	0.751313	0.027*
H4B	0.843582	0.431497	0.862068	0.027*
C5	0.7883 (7)	0.3862 (5)	0.5963 (4)	0.0248 (11)
H5A	0.703672	0.432445	0.547367	0.037*
H5B	0.915497	0.404192	0.564350	0.037*
H5C	0.783268	0.283036	0.600084	0.037*
C6	0.7179 (7)	0.6079 (5)	0.7113 (4)	0.0252 (11)
H6A	0.813789	0.638607	0.648547	0.030*
H6B	0.739459	0.642035	0.784564	0.030*
C7	0.5209 (6)	0.6717 (5)	0.6914 (4)	0.0203 (10)
H7A	0.507902	0.777404	0.691491	0.024*
H7B	0.502552	0.642083	0.615938	0.024*
C8	0.3699 (7)	0.6894 (5)	0.8977 (4)	0.0240 (11)
H8A	0.275110	0.653142	0.956793	0.036*
H8B	0.491658	0.667867	0.920385	0.036*
H8C	0.338952	0.793064	0.888771	0.036*
C9	0.1845 (6)	0.6579 (5)	0.7540 (4)	0.0238 (11)
H9A	0.183045	0.613796	0.681219	0.036*
H9B	0.090260	0.623030	0.814238	0.036*
H9C	0.157198	0.762008	0.746184	0.036*
C10	0.2343 (11)	−0.0099 (7)	0.5611 (6)	0.0552 (18)
H10A	0.099346	0.018269	0.579087	0.083*
H10B	0.261222	−0.109953	0.537796	0.083*
H10C	0.288970	0.050910	0.498446	0.083*
H1O	0.340 (12)	0.100 (4)	0.660 (8)	0.09 (3)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cu1	0.0138 (4)	0.0291 (4)	0.0137 (4)	−0.0029 (2)	−0.0019 (2)	−0.0033 (2)
Cl1	0.0148 (6)	0.0331 (7)	0.0169 (6)	−0.0028 (5)	−0.0014 (4)	−0.0012 (5)
Cl2	0.0205 (6)	0.0397 (7)	0.0172 (6)	−0.0054 (5)	−0.0045 (5)	−0.0061 (5)
O1	0.051 (3)	0.035 (2)	0.048 (3)	−0.004 (2)	−0.011 (2)	0.002 (2)
N1	0.015 (2)	0.034 (2)	0.017 (2)	−0.0042 (17)	−0.0016 (16)	−0.0066 (17)
N2	0.016 (2)	0.032 (2)	0.018 (2)	0.0005 (17)	−0.0003 (16)	−0.0051 (17)
N3	0.0137 (19)	0.027 (2)	0.018 (2)	−0.0030 (16)	−0.0018 (16)	0.0003 (16)
N4	0.014 (2)	0.029 (2)	0.016 (2)	−0.0010 (16)	−0.0043 (16)	−0.0031 (16)
C1	0.026 (3)	0.024 (3)	0.029 (3)	−0.005 (2)	0.000 (2)	−0.001 (2)
C2	0.029 (3)	0.029 (3)	0.032 (3)	0.001 (2)	−0.001 (2)	0.000 (2)
C3	0.021 (3)	0.034 (3)	0.031 (3)	0.009 (2)	−0.004 (2)	−0.005 (2)
C4	0.016 (2)	0.033 (3)	0.021 (3)	−0.003 (2)	−0.005 (2)	0.000 (2)
C5	0.022 (3)	0.037 (3)	0.015 (2)	−0.005 (2)	−0.002 (2)	−0.003 (2)
C6	0.017 (3)	0.032 (3)	0.026 (3)	−0.006 (2)	−0.004 (2)	0.002 (2)
C7	0.020 (2)	0.025 (3)	0.017 (2)	−0.0057 (19)	−0.0028 (19)	0.0032 (19)
C8	0.025 (3)	0.034 (3)	0.014 (2)	−0.005 (2)	−0.003 (2)	−0.007 (2)
C9	0.011 (2)	0.035 (3)	0.024 (3)	−0.001 (2)	−0.001 (2)	−0.002 (2)
C10	0.066 (5)	0.054 (4)	0.050 (4)	−0.015 (4)	−0.014 (4)	−0.002 (3)

Geometric parameters (Å, º) top

Cu1—N1	1.991 (4)	C3—H3	0.9300
Cu1—N4	2.043 (4)	C4—H4A	0.9700
Cu1—N3	2.125 (4)	C4—H4B	0.9700
Cu1—Cl1	2.2914 (15)	C5—H5A	0.9600
Cu1—Cl2	2.4630 (15)	C5—H5B	0.9600
O1—C10	1.439 (7)	C5—H5C	0.9600
O1—H1O	0.91 (2)	C6—C7	1.522 (6)
N1—C1	1.322 (6)	C6—H6A	0.9700
N1—N2	1.346 (5)	C6—H6B	0.9700
N2—C3	1.327 (6)	C7—H7A	0.9700
N2—C4	1.459 (6)	C7—H7B	0.9700
N3—C4	1.473 (6)	C8—H8A	0.9600
N3—C5	1.473 (6)	C8—H8B	0.9600
N3—C6	1.488 (6)	C8—H8C	0.9600
N4—C8	1.475 (6)	C9—H9A	0.9600
N4—C7	1.484 (6)	C9—H9B	0.9600
N4—C9	1.493 (6)	C9—H9C	0.9600
C1—C2	1.396 (7)	C10—H10A	0.9600
C1—H1	0.9300	C10—H10B	0.9600
C2—C3	1.375 (7)	C10—H10C	0.9600
C2—H2	0.9300

N1—Cu1—N4	156.67 (16)	N3—C4—H4A	110.6
N1—Cu1—N3	78.82 (16)	N2—C4—H4B	110.6
N4—Cu1—N3	85.33 (15)	N3—C4—H4B	110.6
N1—Cu1—Cl1	92.42 (12)	H4A—C4—H4B	108.7
N4—Cu1—Cl1	96.09 (11)	N3—C5—H5A	109.5
N3—Cu1—Cl1	157.90 (11)	N3—C5—H5B	109.5
N1—Cu1—Cl2	102.33 (12)	H5A—C5—H5B	109.5
N4—Cu1—Cl2	96.90 (11)	N3—C5—H5C	109.5
N3—Cu1—Cl2	98.84 (11)	H5A—C5—H5C	109.5
Cl1—Cu1—Cl2	102.86 (6)	H5B—C5—H5C	109.5
C10—O1—H1O	106 (5)	N3—C6—C7	108.4 (4)
C1—N1—N2	105.4 (4)	N3—C6—H6A	110.0
C1—N1—Cu1	140.6 (3)	C7—C6—H6A	110.0
N2—N1—Cu1	114.0 (3)	N3—C6—H6B	110.0
C3—N2—N1	111.5 (4)	C7—C6—H6B	110.0
C3—N2—C4	131.2 (4)	H6A—C6—H6B	108.4
N1—N2—C4	117.1 (4)	N4—C7—C6	109.2 (4)
C4—N3—C5	110.2 (4)	N4—C7—H7A	109.8
C4—N3—C6	112.7 (4)	C6—C7—H7A	109.8
C5—N3—C6	111.0 (4)	N4—C7—H7B	109.8
C4—N3—Cu1	104.4 (3)	C6—C7—H7B	109.8
C5—N3—Cu1	112.5 (3)	H7A—C7—H7B	108.3
C6—N3—Cu1	105.7 (3)	N4—C8—H8A	109.5
C8—N4—C7	111.4 (4)	N4—C8—H8B	109.5
C8—N4—C9	107.1 (4)	H8A—C8—H8B	109.5
C7—N4—C9	109.0 (3)	N4—C8—H8C	109.5
C8—N4—Cu1	110.6 (3)	H8A—C8—H8C	109.5
C7—N4—Cu1	105.1 (3)	H8B—C8—H8C	109.5
C9—N4—Cu1	113.6 (3)	N4—C9—H9A	109.5
N1—C1—C2	111.1 (5)	N4—C9—H9B	109.5
N1—C1—H1	124.4	H9A—C9—H9B	109.5
C2—C1—H1	124.4	N4—C9—H9C	109.5
C3—C2—C1	104.1 (5)	H9A—C9—H9C	109.5
C3—C2—H2	127.9	H9B—C9—H9C	109.5
C1—C2—H2	127.9	O1—C10—H10A	109.5
N2—C3—C2	107.8 (5)	O1—C10—H10B	109.5
N2—C3—H3	126.1	H10A—C10—H10B	109.5
C2—C3—H3	126.1	O1—C10—H10C	109.5
N2—C4—N3	105.9 (4)	H10A—C10—H10C	109.5
N2—C4—H4A	110.6	H10B—C10—H10C	109.5

C1—N1—N2—C3	−0.3 (5)	N1—N2—C4—N3	−36.6 (5)
Cu1—N1—N2—C3	−179.1 (3)	C5—N3—C4—N2	−75.1 (4)
C1—N1—N2—C4	−175.1 (4)	C6—N3—C4—N2	160.2 (4)
Cu1—N1—N2—C4	6.1 (5)	Cu1—N3—C4—N2	45.9 (4)
N2—N1—C1—C2	0.5 (5)	C4—N3—C6—C7	−149.4 (4)
Cu1—N1—C1—C2	178.8 (4)	C5—N3—C6—C7	86.4 (5)
N1—C1—C2—C3	−0.4 (6)	Cu1—N3—C6—C7	−35.9 (4)
N1—N2—C3—C2	0.0 (6)	C8—N4—C7—C6	72.7 (5)
C4—N2—C3—C2	173.9 (5)	C9—N4—C7—C6	−169.3 (4)
C1—C2—C3—N2	0.2 (6)	Cu1—N4—C7—C6	−47.2 (4)
C3—N2—C4—N3	149.9 (5)	N3—C6—C7—N4	57.5 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···Cl1ⁱ	0.93	2.98	3.841 (6)	156
C3—H3···O1ⁱⁱ	0.93	2.62	3.305 (7)	131
C4—H4A···Cl2ⁱⁱ	0.97	2.67	3.636 (5)	173
C4—H4B···Cl1ⁱⁱⁱ	0.97	2.94	3.902 (5)	170
C5—H5A···Cl2^iv	0.96	2.93	3.745 (5)	143
C7—H7A···O1^v	0.97	2.42	3.281 (6)	148
C7—H7B···Cl2^iv	0.97	2.83	3.632 (5)	140
C8—H8A···Cl1	0.96	2.85	3.414 (5)	119
C8—H8B···Cl1ⁱⁱⁱ	0.96	2.81	3.736 (5)	162
C9—H9A···Cl2	0.96	2.76	3.387 (5)	124
O1—H1O···Cl2	0.91 (2)	2.16 (3)	3.047 (4)	164 (7)

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

Acknowledgements

The Department of Chemistry, M.S.J. Govt. (PG) College Bharatpur, Rajasthan, and the Department of Chemistry, L·S. College, B·R.A. Bihar University, are thanked for providing laboratory facilities.

References

Arroyo, N., Gómez-de la Torre, F., Jalón, F. A., Manzano, B. R., Moreno-Lara, B. & Rodríguez, A. M. (2000). J. Organomet. Chem. 603, 174–184. CrossRef CAS Google Scholar
Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Bruker (2007). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Faizi, Md. S. H., Alam, M. J., Haque, A., Ahmad, S., Shahid, M. & Ahmad, M. (2018). J. Mol. Struct. 1156, 457–464. CrossRef CAS Google Scholar
Faizi, M. S. H. & Sen, P. (2014). Acta Cryst. E70, m206–m207. CSD CrossRef IUCr Journals Google Scholar
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854. Web of Science CrossRef CAS IUCr Journals Google Scholar
Finney, L., Vogt, S., Fukai, T. & Glesne, D. (2009). Clin. Exp. Pharmacol. Physiol. 36, 88–94. Web of Science CrossRef PubMed CAS Google Scholar
García-Antón, G., Pons, J., Solans, X., Font-Bardia, M. & Ros, J. (2003). Eur. J. Inorg. Chem. pp. 2992–3000. Google Scholar
Kumar, A., Faizi, M. S. H., Javed, S., Siddiqui, N. & Iskenderov, T. (2019). IUCrData, 4, x190050–x190050. Google Scholar
Kumar, M., Kumar, A., Faizi, Md. S. H., Kumar, S., Singh, M. K., Sahu, S. K., Kishor, S. & John, R. P. (2018). Sens. Actuators B Chem. 260, 888–899. CrossRef CAS Google Scholar
Morin, T. J., Wanniarachchi, S., Gwengo, C., Makura, V., Tatlock, H. M., Lindeman, S. V., Bennett, B., Long, G. J., Grandjean, F. & Gardinier, J. R. (2011). Dalton Trans. 40, 8024–8034. Web of Science CSD CrossRef CAS PubMed Google Scholar
Mukherjee, R. (2000). Coord. Chem. Rev. 203, 151–218. Web of Science CrossRef CAS Google Scholar
Pal, S., Barik, A. K., Gupta, S., Hazra, A., Kar, S. K., Peng, S.-M., Lee, G.-H., Butcher, R. J., El Fallah, M. S. & Ribas, J. (2005). Inorg. Chem. 44, 3880–3889. Web of Science CSD CrossRef PubMed CAS Google Scholar
Shaw, J. L., Cardon, T. B., Lorigan, G. A. & Ziegler, C. J. (2004). Eur. J. Inorg. Chem. pp. 1073–1080. CSD CrossRef Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Sheldrick, G. M. (2015). Acta Cryst. C71, 3–8. Web of Science CrossRef IUCr Journals Google Scholar
Turski, M. L. & Thiele, D. J. (2009). J. Biol. Chem. 284, 717–721. Web of Science CrossRef PubMed CAS Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar
Zhang, J., Li, A. F. & Hor, T. S. A. (2009). Dalton Trans. pp. 9327–9333. CrossRef Google Scholar

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