Home Crystal structure of [4-chloro-2-(((2-((3-ethoxy-2-oxidobenzylidene)amino)phenyl)imino)(phenyl)methyl)phenolato-κ4N,N′,O,O′}nickel(II) - ethyl acetate (1/1), C32H29ClN2NiO5
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Crystal structure of [4-chloro-2-(((2-((3-ethoxy-2-oxidobenzylidene)amino)phenyl)imino)(phenyl)methyl)phenolato-κ4N,N′,O,O′}nickel(II) - ethyl acetate (1/1), C32H29ClN2NiO5

  • Yong Hong EMAIL logo , Wei Liu and Gaozhang Gou
Published/Copyright: August 8, 2018

Abstract

C32H29ClN2NiO5, triclinic, P1̄ (no. 2), a = 9.7657(5) Å, b = 10.1262(6) Å, c = 16.0745(9) Å, α = 83.025(2)°, β = 77.437(2)°, γ = 66.240(2)°, V = 1419.02(14) Å3, Z = 2, Rgt(F) = 0.0403, wRref(F2) = 0.0908, T = 293(2) K.

CCDC no.: 1822661

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:Colorless block
Size:0.32 × 0.21 × 0.11 mm
Wavelength:Mo Kα radiation (0.71073 Å)
μ:0.82 mm−1
Diffractometer, scan mode:Bruker APEX-II, φ and ω-scans
θmax, completeness:25°, >99%
N(hkl)measured, N(hkl)unique, Rint:32913, 4987, 0.053
Criterion for Iobs, N(hkl)gt:Iobs > 2 σ(Iobs), 4029
N(param)refined:372
Programs:Bruker programs [1], SHELX [2]
Table 2:

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

AtomxyzUiso*/Ueq
Ni10.30792(4)0.37454(4)0.64762(2)0.02772(11)
Cl1−0.23263(13)0.32020(12)1.01227(6)0.0815(3)
O20.42601(19)0.47224(19)0.65928(11)0.0341(4)
O30.1748(2)0.4804(2)0.73702(12)0.0391(5)
O10.5733(2)0.5936(2)0.71920(12)0.0437(5)
N10.4329(2)0.2829(2)0.55049(13)0.0279(5)
N20.2014(2)0.2561(2)0.64774(13)0.0275(5)
O50.3524(3)0.1789(3)0.93543(15)0.0694(7)
C230.0529(3)0.3147(3)0.78929(16)0.0302(6)
C80.5644(3)0.4484(3)0.61874(16)0.0302(6)
C160.1132(3)0.2266(3)0.71513(16)0.0278(6)
C240.0796(3)0.4414(3)0.79322(16)0.0316(6)
C150.2452(3)0.1860(3)0.56815(15)0.0276(6)
C100.3713(3)0.2028(3)0.51498(16)0.0274(6)
C120.3538(3)0.0722(3)0.40630(17)0.0392(7)
H120.3909480.0320080.3528850.047*
C170.0767(3)0.0955(3)0.71997(16)0.0306(6)
C30.6490(3)0.5137(3)0.64882(17)0.0333(6)
C110.4249(3)0.1459(3)0.43476(16)0.0349(6)
H110.5091970.1574750.4000470.042*
C25−0.0006(3)0.5311(3)0.86344(17)0.0378(7)
H250.0130760.6163520.8651760.045*
C28−0.0430(3)0.2795(3)0.85994(17)0.0414(7)
H28−0.0569650.1937630.8607120.050*
C130.2263(3)0.0582(3)0.45769(17)0.0397(7)
H130.1769480.0099490.4379610.048*
C70.6362(3)0.3630(3)0.54644(17)0.0325(6)
C140.1717(3)0.1146(3)0.53733(17)0.0349(6)
H140.0853470.1051670.5708360.042*
C22−0.0700(3)0.1067(3)0.72112(17)0.0393(7)
H22−0.1485400.1972150.7195990.047*
C27−0.1152(3)0.3679(3)0.92664(18)0.0446(8)
C90.5633(3)0.2896(3)0.51506(17)0.0327(6)
H90.6127310.2417590.4645110.039*
C20.6604(4)0.6333(4)0.7645(2)0.0498(8)
H2A0.6989210.7008060.7299610.060*
H2B0.7463460.5485530.7779260.060*
C60.7849(3)0.3484(3)0.50412(19)0.0418(7)
H60.8302560.2943620.4554750.050*
C180.1913(3)−0.0394(3)0.72479(17)0.0396(7)
H180.289069−0.0474300.7262380.047*
C26−0.0971(3)0.4965(3)0.92850(17)0.0415(7)
H26−0.1500300.5580860.9734480.050*
C21−0.0994(4)−0.0165(4)0.72453(19)0.0514(9)
H21−0.197897−0.0091010.7257830.062*
C40.7939(3)0.4944(3)0.60712(19)0.0405(7)
H40.8483430.5362890.6277210.049*
C310.3058(5)0.0584(4)0.9518(3)0.0772(12)
H31A0.394328−0.0317280.9499110.093*
H31B0.2495890.0579860.9090790.093*
C50.8609(3)0.4126(3)0.5342(2)0.0443(8)
H50.9583900.4022790.5061060.053*
C190.1621(4)−0.1623(3)0.72748(19)0.0541(9)
H190.239839−0.2530420.7302150.065*
C200.0167(5)−0.1497(4)0.7261(2)0.0611(10)
H20−0.002722−0.2323950.7261650.073*
C10.5594(4)0.7013(4)0.8442(2)0.0716(11)
H1A0.4727890.7827970.8303380.107*
H1B0.6144320.7326330.8747900.107*
H1C0.5256320.6322280.8791230.107*
O40.4719(4)0.1022(4)0.8062(2)0.1100(11)
C290.4823(6)0.3156(5)0.8531(3)0.0885(13)
C320.2080(6)0.0744(5)1.0378(3)0.0997(15)
H32A0.1219500.1648851.0393800.150*
H32B0.2655380.0719841.0797740.150*
H32C0.173125−0.0032311.0498500.150*
C300.4392(5)0.1886(5)0.8603(3)0.0750(12)

Source of material

(E)-2-(((2-aminophenyl)imino)(phenyl)methyl)-4-chlorophenol (mono-imine) was synthesized by the method described [4]. 5-Chloro-2-hydroxybenzophenone (0.233 g, 1 mmol), 1,2-diaminobenzene (0.108 g, 1 mmol), piperidine (0.085 g, 1 mmol), and triethylorthoformate (0.148 g, 1 mmol) were refluxed for 2 h in ethanol (10 mL), then the solution was cooled and the mono-imine was obtained by filtration. Unsymmetrical tetradentate Schiff base ligand (UTSBL) was prepared by the obtained mono-imine and 3-ethyoxyl-2-hydroxybenzaldehyde. The mono-imine (0.323 g, 1 mmol) and 3-methoxy-2-hydroxybenzaldehyde (0.168 g, 1 mmol) were added to the solution of ethanol (10 mL) and refluxed for 2 h. The precipitate thus formed was collected by filtration. UTSBL (0.471 g, 1 mmol) and nickel acetate tetrahydrate (0.249 g, 1 mmol) were refluxed in methanol and ethyl acetate for about 1 h. After filtration, the solution was evaporated slowly at room temperature to obtain green prismatic crystals.

Experimental details

The H atoms were positioned geometrically with d(C—H) = 0.93–0.98 Å and refined as riding with Uiso(H) = 1.2 Ueq(carrier) or 1.5 Ueq(methyl).

Discussion

The complexs of symmetrical or unsymmetrical sal(salphen)tetradentate (N2O2) Schiff bases raise certain concerns for their intriguing applications in various fields [4], [5], [6], [7], [8]. There have been reported similar symmetrical crystal strcutures of Ni(II) [9, 10] . Herein, we report the crystal structure of a similar Ni(II) complex.

The dihedral angles between the aryl rings (C3—C4—C5—C6—C7—C8 and C10—C11—C12—C13—C14—C15), (C3—C4—C5—C6—C7—C8 and C23—C24—C25—C26—C27—C28), (C3—C4—C5—C6—C7—C8 and C17—C18—C19—C20—C21—C22) are 15.19°, 37.47°, 56.80°, respectively. The dihedral angle between the two chelating ring system (Ni—N1—O2—C7—C8—C9 and Ni—N2—O3—C16—C23—C24) is 23.53° which indicated some distortion around the metal center. The packing of crystal structure is via van der Waals forces.

Award Identifier / Grant number: 21461007

Funding statement: This work was financially supported by National Natural Science Foundation of China (Grant No. 21461007) and Open Fund of Master Construction Discipline in Yunnan Province (Grant No. HXB1401).

References

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Received: 2018-05-27
Accepted: 2018-07-26
Published Online: 2018-08-08
Published in Print: 2018-11-27

©2018 Yong Hong et al., published by De Gruyter, Berlin/Boston

This work is licensed under the Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 License.

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