Home Crystal structure of bis(N′-((5-(ethoxycarbonyl)-1H-pyrrol-2-yl)methylene)-N-ethylcarbamohydrazonothioato-κ2N,O)nickel(II), C22H30N8O4S2Ni
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Crystal structure of bis(N′-((5-(ethoxycarbonyl)-1H-pyrrol-2-yl)methylene)-N-ethylcarbamohydrazonothioato-κ2N,O)nickel(II), C22H30N8O4S2Ni

  • Kui-Kui Chen , Jing-Tao Huang , Long Lin ORCID logo EMAIL logo and Wei-Na Wu ORCID logo
Published/Copyright: December 31, 2019

Abstract

C22H30N8O4S2Ni, monoclinic, P21/c (no. 14), a = 10.635(2) Å, b = 10.308(2) Å, c = 12.444(3) Å, β = 101.205(4)°, V = 1338.2(5) Å3, Z = 2, Rgt(F) = 0.0417, wRref(F2) = 0.0937, T = 296(2) K.

CCDC no.: 1970194

The molecular structure is shown in the figure (hydrogen atoms are omitted for clarity.). Table 1 contains crystallographic data and Table 2 contains the list of the atoms including atomic coordinates and displacement parameters.

Table 1:

Data collection and handling.

Crystal:Black block
Size:0.18 × 0.15 × 0.14 mm
Wavelength:Mo Kα radiation (0.71073 Å)
μ:0.93 mm−1
Diffractometer, scan mode:Bruker APEX-II, φ and ω
θmax, completeness:25.0°, >99%
N(hkl)measured, N(hkl)unique, Rint:6691, 2353, 0.045
Criterion for Iobs, N(hkl)gt:Iobs > 2 σ(Iobs), 1692
N(param)refined:171
Programs:SHELX [1], Bruker [2]
Table 2:

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

AtomxyzUiso*/Ueq
S10.44432(8)0.68589(9)0.42404(8)0.0493(3)
Ni10.50000.50000.50000.03433(19)
O1−0.1130(2)0.6728(2)0.6376(2)0.0515(6)
O2−0.1857(2)0.5482(2)0.7619(2)0.0557(7)
N10.1064(2)0.5305(2)0.6593(2)0.0381(7)
H10.09660.58430.60550.046*
N20.3471(2)0.5143(2)0.5600(2)0.0346(6)
N30.2515(2)0.6034(2)0.5176(2)0.0368(6)
N40.2110(2)0.7809(3)0.4063(2)0.0450(7)
H40.23880.83510.36380.054*
C1−0.2329(4)0.8346(4)0.5256(3)0.0655(11)
H1A−0.23540.78180.46160.098*
H1B−0.15730.88760.53700.098*
H1C−0.30750.88900.51550.098*
C2−0.2305(3)0.7496(4)0.6227(3)0.0582(10)
H2A−0.23180.80180.68730.070*
H2B−0.30480.69300.61090.070*
C3−0.1030(3)0.5770(3)0.7113(3)0.0458(9)
C40.0195(3)0.5101(3)0.7256(3)0.0419(8)
C50.0703(3)0.4174(3)0.8012(3)0.0518(10)
H50.03200.38450.85660.062*
C60.1887(3)0.3820(3)0.7801(3)0.0486(9)
H60.24400.32100.81900.058*
C70.2104(3)0.4529(3)0.6911(3)0.0376(8)
C80.3206(3)0.4472(3)0.6414(3)0.0370(8)
H80.38230.38660.67150.044*
C90.2907(3)0.6877(3)0.4521(3)0.0355(8)
C100.0806(3)0.7973(3)0.4230(3)0.0455(9)
H10A0.08170.83280.49540.055*
H10B0.03780.71380.41830.055*
C110.0085(3)0.8879(4)0.3370(3)0.0617(11)
H11A0.00210.84940.26580.093*
H11B0.05360.96880.33930.093*
H11C−0.07590.90290.35110.093*

Source of material

The title complex was synthesized by the reaction of N′-((Z)-(5-(ethoxycarbonyl)-1H-pyrrol-2-yl)methylene)-N-ethylcarbamohydrazonothioic acid (TSCH) (5 mmol) with an equimolar amount of Ni(OAc)2 ⋅ 6H2O in MeOH/THF (20 mL, v:v = 1:1). The reaction mixture was filtered and set aside to crystallize for several days, giving black block crystals.

Experimental details

The structure was solved by direct methods and refined with the SHELX crystallographic software package [1]. The hydrogen atoms were placed at calculated positions and refined as riding atoms with isotropic displacement parameters.

Comment

Thiosemicarbazones (TSCs) and their transition metal complexes have attracted attention in the coordination chemistry because of their high biological and pharmaceutical activities, such as antibacterial, antiviral, antifungal, antitumor activity and so on [3], [4]. It is noted that N(4)-substituted TSCs bearing pyrrole units could act as potential chemotherapeutic agents [5], [6]. Herein, the title Ni(II) complex with a pyrrole-TSC ligand is reported, which was synthesized and characterized by X-ray diffraction.

In the title structure, the asymmetric unit contains one half of the complex with Ni1 atom lying on the inversion center [the figure, symmetry code: (i) −x + 1, −y + 1, −z + 1]. The four-coordinated Ni(II) ion is in a distorted square planar geometry with the donor sets of two N and two S atoms from two dependent TSC ligands. The length of C—S is 1.736(3) Å, which is much longer than that of 1.691(19) Å in the free molecule [6], showing that the TSC ligand has thiolated and deprotonated. Furthermore, the imine C=N (C8—N2) bond adopted a Z configuration instead of E in the free molecule [6]. In the solid state, intermolecular N—H⋯O hydrogen bonds between the terminal amino N and carboxylate O atoms link molecules into a two-dimensional supermolecular network. In addition, the intramolecular N—H⋯N hydrogen bond between the pyrrole N and the imine N (N3) atom is present (see the Figure). All egmetic parameters are similar to those derived for the parent structure [7] and related ones [8].

References

1. Sheldrick, G. M.: Crystal refinement with SHELX. Acta Crystallogr. C71 (2015) 3–8.10.1107/S2053273314026370Search in Google Scholar

2. Bruker. SMART and SAINT. Bruker AXS Inc., Madison, WI, USA (2007).Search in Google Scholar

3. Palanimuthu, D.; Shinde, S. V.; Somasundaram, K.; Samuelson, A. G.: In vitro and in vivo anticancer activity of copper bis(thiosemicarbazone) complexes. J. Med. Chem. 56 (2013) 722–734.10.1021/jm300938rSearch in Google Scholar

4. Matesanz, A. I.; Leitao, I.; Souza, P.: Palladium(II) and platinum(II) bis(thiosemicarbazone) complexes of the 2,6-diacetylpyridine series with high cytotoxic activity in cisplatin resistant A2780cisR tumor cells and reduced toxicity. J. Inorg. Biochem. 125 (2013) 26–31.10.1016/j.jinorgbio.2013.04.005Search in Google Scholar

5. Li, X.-J.; Mao, P.-D.; Wu, W.-N.; Kou, K.; Liu, S.-Y.; Wang, Y.: Ni(II)/Cu(II) complexes with two pyrrole thiosemicarbazone ligands: Crystal structures and DNA interaction. Chin. J. Inorg. Chem. 33 (2017) 1257–1265.Search in Google Scholar

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7. Bermejo, E.; Castineiras, A.; Perez, T.; Carballo, R.; Hiller, W.: Synthesis and structural characterization of metal complexes of 2-formylpyrrole-4N-ethylthiosemicarbazone (4EL1) and 2-acetylpyrrole-4N-ethylthiosemicarbazone (4EL2). Z. Anorg. Allg. Chem. 627 (2001) 2377–2385.10.1002/1521-3749(200110)627:10<2377::AID-ZAAC2377>3.0.CO;2-OSearch in Google Scholar

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Received: 2019-09-12
Accepted: 2019-12-05
Published Online: 2019-12-31
Published in Print: 2020-02-25

©2019 Kui-Kui Chen et al., published by De Gruyter, Berlin/Boston

This work is licensed under the Creative Commons Attribution 4.0 Public License.

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  77. Low temperature redetermination of the crystal structure of catena-poly[[tri-4-fluorobenzyltin(IV)]μ2-pyridine-4-carboxylato-κ2N:O], {C27H22F3NO2Sn}n
  78. Crystal structure of bis(2-propyl-1H-benzo[d]imidazol-3-ium) tetrachloridozincate(II), C10H13Cl4N2Zn
  79. The crystal structure of (Z)-3-hydrazono-5-nitroindolin-2-one – dimethyl sulfoxide (1/1), C8H6N4O3
  80. Crystal structure of bis-[N-(1-pyrazin-2-yl-ethylidene)-cyanoacetic acid-hydrazonato-κ3O,N,N′)]-zinc(II), C18H16N10O2Zn
  81. Crystal structure and photochromism of 1-(2,5-dimethyl-3-thienyl)-2-[2-methyl-5-(benzaldoxime)-3-thienyl] perfluorocyclopentene, C23H17F6NOS2
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