Crystal structure of [6,6′-((1E,1′E)-(propane-1,3- diylbis(azaneylylidene))bis(methaneylylidene)) bis(3-chlorophenol)-κ4N,N′,O,O′] copper(II), C17H14Cl2CuN2O2

Baiying Wei; Chenzhong Cao

doi:10.1515/ncrs-2021-0249

Open Access Published by De Gruyter (O) August 3, 2021

Crystal structure of [6,6′-((1E,1′E)-(propane-1,3- diylbis(azaneylylidene))bis(methaneylylidene)) bis(3-chlorophenol)-κ⁴N,N′,O,O′] copper(II), C₁₇H₁₄Cl₂CuN₂O₂

Baiying Wei and Chenzhong Cao

From the journal Zeitschrift für Kristallographie - New Crystal Structures

https://doi.org/10.1515/ncrs-2021-0249

Abstract

C₁₇H₁₄Cl₂CuN₂O₂, monoclinic, C2/c (no. 15), a = 22.743(4) Å, b = 8.0434(15) Å, c = 8.9388(17) Å, V = 1630.8(5) Å³, Z = 4, R_gt(F) = 0.0376, wR_ref(F²) = 0.0997, T = 296(2) K.

CCDC no.: 2090336

The molecular structure is shown in the figure. 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:	0.22 × 0.18 × 0.14 mm
Wavelength:	Mo Kα radiation (0.71073 Å)
μ:	1.68 mm⁻¹
Diffractometer, scan mode:	Bruker APEX-II, φ and ω
θ_max, completeness:	25.0°, >99%
N(hkl)_measured, N(hkl)_unique, R_int:	4151, 1449, 0.023
Criterion for I_obs, N(hkl)_gt:	I_obs > 2 σ(I_obs), 1154
N(param)_refined:	123
Programs:	Bruker [1], SHELX [2], Olex2 [3]

Table 2:

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

Atom	x	y	z	U_iso*/U_eq
Cu1	0.500000	0.46495 (6)	0.750000	0.0615 (2)
Cl1	0.28741 (5)	−0.06158 (17)	0.44459 (13)	0.1018 (4)
O1	0.44328 (10)	0.2942 (3)	0.7093 (3)	0.0628 (6)
N1	0.45644 (15)	0.6245 (3)	0.6191 (4)	0.0748 (9)
C1	0.40053 (13)	0.2882 (4)	0.6034 (4)	0.0580 (8)
C2	0.36714 (13)	0.1414 (5)	0.5848 (4)	0.0629 (9)
H2	0.373861	0.053845	0.651793	0.075*
C3	0.32476 (14)	0.1267 (6)	0.4684 (4)	0.0737 (10)
C4	0.31140 (18)	0.2532 (7)	0.3696 (5)	0.0928 (13)
H4	0.283212	0.239169	0.289861	0.111*
C5	0.34051 (19)	0.4007 (7)	0.3910 (4)	0.0899 (13)
H5	0.330381	0.488990	0.327046	0.108*
C6	0.38572 (15)	0.4242 (5)	0.5072 (4)	0.0668 (9)
C7	0.41233 (19)	0.5829 (5)	0.5270 (5)	0.0768 (10)
H7	0.396109	0.667446	0.466207	0.092*
C8^a	0.4630 (11)	0.8084 (12)	0.618 (3)	0.125 (9)
H8A^a	0.427850	0.859470	0.652911	0.150*
H8B^a	0.467233	0.846092	0.516234	0.150*
C9^a	0.5166 (5)	0.8622 (9)	0.7182 (16)	0.100 (4)
H9A^a	0.551721	0.827456	0.671390	0.120*
H9B^a	0.517028	0.982707	0.722659	0.120*
C10^a	0.5200 (10)	0.7979 (13)	0.872 (2)	0.103 (9)
H10A^a	0.481044	0.799724	0.909843	0.123*
H10B^a	0.545369	0.869600	0.936092	0.123*

^aOccupancy: 0.5.

Source of material

The title salen-type Schiff base ligand was prepared according to the literature method [4, 5] and the title complex was prepared according to the literature reported earlier [6]. The ethanol solution (20 ml) of the copper(II) acetate monohydrate (2 mmol) was slowly added into the ethanol solution (10 ml) of the title Schiff base ligand (2 mmol). The resulting mixture was kept being stirred for 1 h at room temperature until precipitation occurs. The product was collected by filtration and washed with ethanol solution. Then the product was dissolved in anhydrous ethanol and allowed to stand at room temperature 30 days in a quiet environment. Several block crystals were obtained.

Experimental details

H atoms were geometrically added and isotropically refined by the riding model. The propan-diyl moiety is disordered (see the Figure).

Comment

Some salen-type Schiff base complexes show photophysical properties, extensive attention has been attracted and were applied to many fields [7, 8]. And copper salen-type Schiff base complexes are amongst the most versatile catalysts known for oxygenation reactions [9]. So, a variety of salen-type complexes have been synthesized and investigated [10], [11], [12], [13].

In the crystal structure of the title compound the Cu atom is four-coordinated by two O atoms and two N atoms of the corresponding salen-type Schiff base ligand forming a tetrahedral N₂O₂ coordination mode. The bond lengths of Cu1–O1 is 1.901(2) Å and the Cu1–N1 is 1.957(3) Å. The angles of N1–Cu1–O1, N1–Cu1–N1′, O1–N1–O1′ and N1–Cu1–O1′ are 93.00(2), 98.0(2), 87.50(13) and 153.53(11)°, respectively.

Corresponding author: Chenzhong Cao, School of Resource Environment and Safety Engineering, School of Chemistry and Chemical Engineering, Key Laboratory of Theoretical Organic Chemistry and Function Molecule, Ministry of Education, Hunan University of Science and Technology, Xiangtan, 411201, P. R. China, E-mail: czcao@hnust.edu.cn

Funding source: National Natural Science Foundation of China

Award Identifier / Grant number: 21672058

Author contributions: All the authors have accepted responsibility for the entire content of this submitted manuscript and approved submission.
Research funding: The work was supported by the National Natural Science Foundation of China (21672058).
Conflict of interest statement: The authors declare no conflicts of interest regarding this article.

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Received: 2021-06-18

Accepted: 2021-07-20

Published Online: 2021-08-03

Published in Print: 2021-12-20

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