The crystal structure of bis((E)-2-((tert-butylimino)methyl)-4-chlorophenolato-κ2N,O)zinc(II), C22H26Cl2N2O2Zn

Qian-Zhi Yang; Yu-Xin Yang; Jin-Hao Kuang; Zhong-Yan Li; Lin Yuan

doi:10.1515/ncrs-2022-0049

Open Access Published by De Gruyter (O) March 22, 2022

The crystal structure of bis((E)-2-((tert-butylimino)methyl)-4-chlorophenolato-κ²N,O)zinc(II), C₂₂H₂₆Cl₂N₂O₂Zn

Qian-Zhi Yang , Yu-Xin Yang , Jin-Hao Kuang , Zhong-Yan Li and Lin Yuan

From the journal Zeitschrift für Kristallographie - New Crystal Structures

https://doi.org/10.1515/ncrs-2022-0049

Abstract

C₂₂H₂₆Cl₂N₂O₂Zn, monoclinic, P2₁/n (no. 14), a = 10.488(7) Å, b = 10.139(7) Å, c = 22.760(15) Å, β = 99.705°, V = 2386(3) Å³, Z = 4, R_gt(F) = 0.0395, wR_ref(F²) = 0.1053, T = 296(2) K.

CCDC no.: 2104194

The molecular structure is shown in 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:	Block
Size:	039×0.37×0.32 mm
Wavelength:	Mo Kα radiation (0.71073 Å)
μ:	1.27 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:	21,975, 4208, 0.022
Criterion for I_obs, N(hkl)_gt:	I_obs > 2σ(I_obs), 3749
N(param)_refined:	269
Programs:	Bruker [1], SHELX [2, 3]

Table 2:

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

Atom	x	y	z	U_iso*/U_eq
C1	0.5995 (3)	0.2509 (3)	0.83077 (13)	0.0468 (7)
C2	0.5307 (3)	0.3638 (3)	0.84439 (13)	0.0479 (7)
C3	0.5220 (3)	0.3852 (4)	0.90477 (15)	0.0602 (8)
H3	0.477820	0.459169	0.914832	0.072*
C4	0.5759 (4)	0.3019 (4)	0.94885 (16)	0.0676 (10)
H4	0.569398	0.319941	0.988300	0.081*
C5	0.6403 (4)	0.1904 (4)	0.93484 (16)	0.0724 (10)
C6	0.6530 (4)	0.1659 (4)	0.87754 (16)	0.0656 (9)
H6	0.697992	0.091333	0.868879	0.079*
C7	0.6265 (3)	0.2160 (3)	0.77272 (14)	0.0487 (7)
H7	0.681693	0.144516	0.771691	0.058*
C8	0.6306 (3)	0.2224 (3)	0.66711 (14)	0.0540 (8)
C9	0.6852 (7)	0.0843 (5)	0.6723 (2)	0.120 (2)
H9A	0.757108	0.080710	0.704495	0.180*
H9B	0.713665	0.060668	0.635735	0.180*
H9C	0.619537	0.023707	0.679854	0.180*
C10	0.7323 (7)	0.3157 (7)	0.6552 (3)	0.173 (4)
H10A	0.699773	0.404319	0.654814	0.259*
H10B	0.756006	0.295834	0.617272	0.259*
H10C	0.806776	0.307431	0.685913	0.259*
C11	0.5185 (6)	0.2248 (8)	0.6173 (2)	0.145 (3)
H11A	0.451245	0.168738	0.626949	0.217*
H11B	0.545499	0.193922	0.581494	0.217*
H11C	0.486592	0.313433	0.611474	0.217*
C12	0.3291 (3)	0.6265 (3)	0.61896 (12)	0.0434 (6)
C13	0.4603 (3)	0.6507 (3)	0.64277 (14)	0.0491 (7)
C14	0.5204 (4)	0.7571 (3)	0.61840 (18)	0.0690 (10)
H14	0.606939	0.774886	0.633021	0.083*
C15	0.4561 (4)	0.8352 (4)	0.57401 (18)	0.0712 (10)
H15	0.498993	0.904379	0.558884	0.085*
C16	0.3279 (4)	0.8111 (3)	0.55180 (15)	0.0609 (9)
C17	0.2658 (3)	0.7094 (3)	0.57353 (14)	0.0545 (8)
H17	0.179186	0.694087	0.558065	0.065*
C18	0.2506 (3)	0.5234 (3)	0.63836 (13)	0.0441 (6)
H18	0.163975	0.523567	0.620653	0.053*
C19	0.1828 (3)	0.3364 (3)	0.69065 (15)	0.0517 (7)
C20	0.0961 (5)	0.2880 (5)	0.6346 (2)	0.1034 (17)
H20A	0.043649	0.359561	0.616584	0.155*
H20B	0.041286	0.218665	0.644755	0.155*
H20C	0.148417	0.255011	0.607097	0.155*
C21	0.1029 (5)	0.4042 (5)	0.7313 (2)	0.0962 (15)
H21A	0.158349	0.432471	0.766995	0.144*
H21B	0.039513	0.343726	0.741398	0.144*
H21C	0.060000	0.479384	0.711273	0.144*
C22	0.2519 (4)	0.2214 (5)	0.7239 (3)	0.1036 (18)
H22A	0.304695	0.178342	0.699035	0.155*
H22B	0.189494	0.160066	0.734129	0.155*
H22C	0.305548	0.252541	0.759530	0.155*
Cl1	0.7118 (2)	0.08261 (17)	0.99087 (6)	0.1442 (7)
Cl2	0.24555 (13)	0.91344 (12)	0.49620 (5)	0.0953 (4)
N1	0.5846 (2)	0.2705 (2)	0.72221 (10)	0.0431 (5)
N2	0.2841 (2)	0.4317 (2)	0.67665 (11)	0.0420 (5)
O1	0.4771 (2)	0.4484 (2)	0.80495 (10)	0.0632 (6)
O2	0.5291 (2)	0.5823 (2)	0.68545 (11)	0.0637 (6)
Zn1	0.46723 (3)	0.42824 (3)	0.72054 (2)	0.04662 (14)

Source of material

(E)-2-((tert-Butylimino)methyl)-4-chlorophenol (1.16 g, 5.5 mmol), zinc acetate monohydrate (0.50 g, 2.5 mmol) and ethanol (80 mL) were heated and stirred at 373 K for 6 h, then cooled to room temperature, resulting in a yellow solution. Crystals of the title compound were obtained by slow evaporation within three days.

Experimental details

All hydrogen atoms were identified in difference Fourier syntheses. The U_iso values of the hydrogen atoms of methyl groups were set to 1.5U_eq(C) and the U_iso values of all other hydrogen atoms were set to 1.2U_eq(C).

Comment

Salicylaldehyde Schiff base is a kind of ligand, which can form complexes with many metal ions [4], [5], [6], [7]. Salicylaldehyde Schiff base metal complexes are widely used in catalysis and so on [8], [9], [10].

The crystal structure shows that the zinc complex has a distorted tetrahedral structure and the Zn is four-coordinated by two phenol oxygen atoms and imine nitrogen atoms of two Schiff bases. The Zn–O distance (O1–Zn1 = 1.917(3) Å; O2–Zn1 = 1.917(2) Å) and the Zn–N length (N1–Zn1 = 2.014(3) Å; N2–Zn1 = 2.010(3) Å) are similar to those seen in related complexes [11, 12]. The C=N bond distance is 1.285(4) Å (C7=N1) and 1.282(4) Å (C18=N2), respectively. The O–Zn–N bond angles are 97.81(9)° (O1–Zn1–N1) and 98.11(10)° (O2–Zn1–N2). Moreover, the coordination of the two NO bidentate chelate ligands to the Zn ion results in the formation of two six-membered rings.

Corresponding authors: Zhong-Yan Li and Lin Yuan, College of Chemistry and Bioengineering, Hunan University of Science and Engineering, Yongzhou, Hunan 425199, P. R. China, E-mail: lizhongyandongdong@126.com (Z.-Y. Li), tcyl431102@163.com (L. Yuan) (L. Yuan)

Author contributions: All the authors have accepted responsibility for the entire content of this submitted manuscript and approved submission.
Research funding: Natural Science Foundation of Hunan Province of China (2021JJ30291), the Scientific Research Fund of Hunan Provincial Education Department (21A0518, 21C0691), Undergraduate Training Program for Innovation and Entrepreneurship of Hunan Province of China ([2021]197-3585), Undergraduate Training Program for Innovation and Entrepreneurship of Hunan University of Science and Enginerring (2021), Yongzhou Guiding Science and Technology Plan (2021), the construct program of applied characteristic discipline in Hunan University of Science and Engineering.
Conflict of interest statement: The authors declare no conflicts of interest regarding this article.

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Received: 2022-01-25

Accepted: 2022-03-11

Published Online: 2022-03-22

Published in Print: 2022-06-27

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