Home Crystal structure of 2,2′-[ethane-1,2-diylbis(azanylylidenemethylylidene)]bis(6-chlorophenol), C16H14Cl2N2O2
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Crystal structure of 2,2′-[ethane-1,2-diylbis(azanylylidenemethylylidene)]bis(6-chlorophenol), C16H14Cl2N2O2

  • Weili Li ORCID logo EMAIL logo and Bo Yang
Published/Copyright: February 11, 2021

Abstract

C16H14Cl2N2O2, monoclinic, P21/n (no. 14), a = 6.8492(14) Å, b = 11.515(2) Å, c = 10.018(2) Å, β = 107.11(3)°, V = 755.2(3) Å3, Z = 2, Rgt(F) = 0.0592, wRref(F2) = 0.1369, T = 293(2) K.

CCDC no.: 2052614

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:Yellow block
Size:0.18 × 0.16 × 0.12 mm
Wavelength:Mo Kα radiation (0.71073 Å)
μ:0.44 mm−1
Diffractometer, scan mode:Bruker D8/APEX2, ω
θmax, completeness:26.4°, >99%
N(hkl)measured, N(hkl)unique, Rint:3010, 1550, 0.060
Criterion for Iobs, N(hkl)gt:Iobs > 2 σ(Iobs), 1110
N(param)refined:101
Programs:Bruker [1], Olex2 [2], SHELX [3], [, 4]
Table 2:

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

AtomxyzUiso*/Ueq
Cl10.24538 (13)0.73733 (6)0.50866 (9)0.0438 (3)
O10.2004 (3)0.30936 (16)0.3632 (2)0.0393 (5)
H10.1735190.3410510.2866720.059*
N10.1417 (3)0.47566 (19)0.1863 (2)0.0308 (5)
C10.2225 (3)0.5104 (2)0.4306 (3)0.0270 (6)
C20.2387 (4)0.3907 (2)0.4641 (3)0.0313 (6)
C30.2967 (4)0.3548 (3)0.6029 (3)0.0373 (7)
H30.3075000.2760260.6241930.045*
C40.3378 (4)0.4354 (3)0.7083 (3)0.0401 (7)
H40.3784070.4104090.8006260.048*
C50.3202 (4)0.5531 (3)0.6799 (3)0.0380 (7)
H50.3457330.6070480.7520920.046*
C60.2644 (4)0.5887 (2)0.5435 (3)0.0309 (6)
C70.1744 (4)0.5486 (2)0.2867 (3)0.0290 (6)
H70.1671440.6277330.2670500.035*
C80.1024 (4)0.5202 (2)0.0449 (3)0.0321 (6)
H8A0.2080520.4934010.0057400.039*
H8B0.1057230.6044280.0470110.039*

Source of material

2-Chloro-6-hydroxybenzaldehyde and 30 ml of anhydrous methanol were added in a conical flask, monitored with a temperature probe and warmed up to 60 °C with stirring. Then 1.0 mmol of ethylenediamine was dropwisely added. Over 30 min the mixture gradually turned to light yellow, and was refluxed for another 16 h. The obtained solution was filtered and the filtrate was left to crystallise in an open vessel at room temperature. Colorless plates crystals were isolated from the yellow mother liquor.

Experimental details

The structure was solved with the Olex2 program [2] as an interface with the SHELXT and SHELXL programs [3], [, 4]. All H atoms were placed in geometrically idealized positions and refined using a riding model, with O–H = 0.84 (phenolic hydroxyl), 0.95 Å (benzene), and with Uiso(H) = 1.2 Ueq(C) for H atoms on phenolic hydroxyl and benzene.

Comment

Schiff bases are the condensation products of primary amines and carbonyl compounds and structurally characterized by carbon-nitrogen double bond group []. Owing to the special pharmacological and physiological properties, this class of compounds has been developed as a research focus for many fields such as magnetism, catalysis, electrochemistry, chemical sensor and supramolecular chemistry etc. [9], [10], [11], [12]. As a part of our current research interest in halogenated Schiff-base compounds, in this work, we report a new hydrazone-based compound.

The centrosymmetric title molecule is shown in the figure. There is an intramolecular hydrogen bond [O(1)–H(1)⋯N(1)] in the asymmetric unit, which forms a S(6) ring plane between the phenolic oxygen atom and the diamine nitrogen atom. The S(6) ring is parallel to the aryl moiety. The whole molecule exhibits a centrosymmetric “Z-type” geometry. Further analysis revealed that intermolecular C–H⋯π hydrogen bonds and aromatic face-to-face π–π interactions play important roles for the crystal packing. [Interactions: C(7)–H(7)⋯Cg(1) with distance = 3.332(2) Å; Cg1⋯Cg1′ (′ = -x, 1-y, 1-z): = 3.734(2) and Cg1⋯Cg1″ (″ = 1-x, 1-y, 1-z): 3.753(2) Å [Cg1 is the centroid of the C1–C6 ring]. All bond lengths and angles are in the expected ranges [13].


Corresponding author: Weili Li, Department of Chemical Science and Technology, Kunming University, Yunnan, Kunming65200, P. R. China, E-mail:

Funding source: Yunnan Fundamental Research Projects

Award Identifier / Grant number: 2019FH001(-091

Award Identifier / Grant number: )

  1. Author contributions: All the authors have accepted responsibility for the entire content of this submitted manuscript and approved submission.

  2. Research funding: Fund for Yunnan Fundamental Research Projects (Grant No. 2019FH001(-091)).

  3. Conflict of interest statement: The authors declare no conflicts of interest regarding this article.

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Received: 2020-12-27
Published Online: 2021-02-11
Published in Print: 2021-05-26

© 2021 Weili Li and Bo Yang, published by De Gruyter, Berlin/Boston

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

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