Home Crystal structure of tetrakis(n-butyl)-(μ2-1,2-bis(2-oxidobenzoyl)hydrazine-1,2-diido-κ6N,O,O′:N′,O′′,O′′′)ditin(IV), C30H44N2O4Sn2
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Crystal structure of tetrakis(n-butyl)-(μ2-1,2-bis(2-oxidobenzoyl)hydrazine-1,2-diido-κ6N,O,O′:N′,O′′,O′′′)ditin(IV), C30H44N2O4Sn2

  • Zhang Cuihong , Wei Xiaohu , Yang Liguo , He Zhenzhen , Wu Jiaze , Liu Hao , Li Xin and Miao Zongcheng EMAIL logo
Published/Copyright: November 30, 2018

Abstract

C30H44N2O4Sn2, monoclinic, P21/c, a = 8.8810(8) Å, b = 16.8999(13) Å, c = 10.5705(10) Å, β = 92.0460(10)°, V = 1585.5(2) Å3, Z = 2, Rgt(F) = 0.0660, wRref(F2) = 0.1528, T = 298(2) K.

CCDC no.: 1873753

The crystal structure is shown in the figure. Tables 1 and 2 contain details on crystal structure and measurement conditions and a list of the atoms including atomic coordinates and displacement parameters.

Table 1:

Data collection and handling.

Crystal:Red block
Size:0.26 × 0.16 × 0.10 mm
Wavelength:Mo Kα radiation (0.71073 Å)
μ:1.61 mm−1
Diffractometer, scan mode:SMART CCD, φ and ω
θmax, completeness:25.0°, 99%
N(hkl)measured, N(hkl)unique, Rint:7943, 2782, 0.069
Criterion for Iobs, N(hkl)gt:Iobs > 2 σ(Iobs), 1637
N(param)refined:174
Programs:Bruker [1], SHELX [2, 3]
Table 2:

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

AtomxyzUiso*/Ueq
Sn10.72189(7)−0.01162(4)0.43518(5)0.0693(3)
N10.9354(7)0.0048(3)0.5363(6)0.0582(17)
O11.1006(7)0.0310(4)0.6964(5)0.0813(18)
O20.6280(7)0.0155(4)0.6044(5)0.0804(18)
C10.9675(11)0.0221(5)0.6546(8)0.064(2)
C20.8425(9)0.0318(5)0.7442(7)0.0604(19)
C30.8943(10)0.0495(5)0.8696(7)0.067(2)
H30.99720.05330.88810.081*
C40.7939(10)0.0612(5)0.9641(8)0.075(2)
H40.82940.06881.04700.090*
C50.6442(11)0.0617(5)0.9367(8)0.074(2)
H50.57680.07270.99970.089*
C60.5925(10)0.0462(5)0.8166(8)0.076(2)
H60.48910.04600.79920.091*
C70.6888(10)0.0307(5)0.7195(7)0.063(2)
C80.763(2)−0.3159(10)0.4022(18)0.248(8)
H8A0.6814−0.31040.34050.372*
H8B0.7785−0.37090.42090.372*
H8C0.8528−0.29380.36930.372*
C90.7244(17)−0.2733(7)0.5200(16)0.188(5)
H9A0.7783−0.29680.59210.226*
H9B0.6173−0.27780.53330.226*
C100.7681(14)−0.1853(7)0.5085(15)0.165(5)
H10A0.7737−0.16290.59300.198*
H10B0.8685−0.18280.47550.198*
C110.6661(12)−0.1330(6)0.4267(11)0.119(4)
H11A0.5632−0.13950.45270.143*
H11B0.6703−0.15050.33950.143*
C120.775(2)0.2489(9)0.1736(15)0.230(7)
H12A0.87860.23690.16060.346*
H12B0.75460.30290.15050.346*
H12C0.71190.21450.12210.346*
C130.7411(17)0.2367(7)0.3107(15)0.174(5)
H13A0.63390.24390.32160.209*
H13B0.79400.27660.36110.209*
C140.7875(14)0.1546(6)0.3589(13)0.151(4)
H14A0.87470.13680.31400.181*
H14B0.81650.15810.44810.181*
C150.6617(11)0.0941(5)0.3414(10)0.100(3)
H15A0.64350.08370.25190.119*
H15B0.56960.11490.37530.119*

Source of material

N-(2-hydroxybenzoyl)-2-hydroxybenzoyl hydrazide was synthesized according to the reference [4]. The other reagents were commercially available and used as purchased [2, 3, 5].

Experimental details

A mixture of bissalicylhydrazide (88.88 mg, 0.4 mmol), tetrabutylammonium hydroxide (103.79 mg, 0.4 mmol), dibutyltin dichloride (208.42 mg, 0.8) and methanol (10 mL) heated at 60 °C for 10 h, and then cooled to room temperature. The resulting block crystals of the compound were obtained and washed with distilled water. The yield is ca. 25%. IR(KBr): 3217(s), 1518(s), 1519(s), 1416(s), 1405(s), 1319(s), 1216(s), 1116(s), 1105(s), 1012(s), 1001(s), 915(s), 819(s), 804(m), 761(m), 721(m), 600(m), 444(m) cm−1.

Comment

Acyl hydrazide complexes have been an important research subject for their extensive biological and pharmacological activity [4]. The activity of its derivatives increased significantly when it formed a stable complex with metal cations in biological cells. In the ligand structure of o-carboxyl, hydroxyl benzoylhydrazide, which is located in the ortho carboxyl group, the hydroxyl group and the amide group have a variety of structure and properties when they coordinate with metal [4], [5], [6]. The hydrazide complexes containing tin(IV) are rare.

The compound crystallizes in the monoclinic space group P21/c with two formula units in the unit cell. As shown in Figure 1, one formula unit consists of one acyl hydrazide ligands, two Sn atoms and four butyl groups. Each Sn ion is fivefold coordinated with one nitrogen atoms, two oxygen atoms from the acyl hydrazide ligand and two carbon atoms from butyl groups. The bond length of Sn—N is 2.161 Å, while the bond length of Sn—O range from 2.052 Å to 2.164 Å, the bond length of Sn—C are 2.103 Å and 2.111 Å.

Figure 1: The molecule structure of the compound.
Figure 1:

The molecule structure of the compound.

Acknowledgements

This work was supported by the National Natural Science Foundation of China (Grant No. 51602007, Grant No. 51673157), the Natural Science Basic Research Plan in Shaanxi Province of China (Grant No. 2017JM5134, Grant No. 2018JM5047), Scientific Research Program Funded by Shaanxi Provincial Education Department (Grant No. 18JK1206), the Science Research Foundation of Xijing University (Grant No. XJ17B07), the National Students’ Platform for Innovation and Entrepreneurship Training Program (Grant No. 201812715003).

References

1. Bruker. SMART and SAINT for Windows NT Software Reference Manuals, Version 5.0, Bruker Analytical X-Ray Systems, Madison, WI (1997).Search in Google Scholar

2. Sheldrick, G. M.: SADABS, a Software for Empirical Absorption Correction. University of Göttingen, Göttingen, Germany (1997).Search in Google Scholar

3. SHELXL Reference Manual, version 5.1. Bruker Analytical X-Ray Systems, Madison, WI (1997).Search in Google Scholar

4. Moon, D.; Lah, M. S.: Size and shape selectivity of host networks built based on tunable secondary building units. Inorg. Chem. 44 (2005) 1934–1940.10.1021/ic0486872Search in Google Scholar PubMed

5. Mondal, S.; Schwederski, B.; Frey, W.; Fiedler, J.; Záliš, S.; Kaim, W.: At the borderline between metal–metal mixed valency and a radical bridge situation: four charge states of a diruthenium complex with a redox-active bis(mer-tridentate) ligand. Inorg. Chem. 57 (2018) 3983–3992.10.1021/acs.inorgchem.8b00173Search in Google Scholar PubMed

6. Cheaib, K.; Martel, D.; Clément, N.; Eckes, F.; Kouaho, S.; Rogez, G.; Dagorne, S.; Kurmoo, M.; Choua, S.; Welter, R.: Structural, magnetic and optical properties of an FeIII dimer bridged by the meridional planar divergent N,N′-bis(salicyl)hydrazide and its photo- and electro-chemistry in solution. Dalton Trans. 42 (2013) 1406–1416.10.1039/C2DT32310ASearch in Google Scholar

Received: 2018-07-29
Accepted: 2018-10-24
Published Online: 2018-11-30
Published in Print: 2019-03-26

©2019 Zhang Cuihong 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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