Home The crystal structure of (E)-2-methoxy-6-(((5-methyl-1,3,4-thiadiazol-2-yl)imino)methyl)phenol, C11H11N3O2S
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The crystal structure of (E)-2-methoxy-6-(((5-methyl-1,3,4-thiadiazol-2-yl)imino)methyl)phenol, C11H11N3O2S

  • Qiuping Huang ORCID logo , Zhenfang Zeng and Qiuchan Huang EMAIL logo
Published/Copyright: November 21, 2023

Abstract

C11H11N3O2S, orthorhombic, Pna21 (no. 33), a = 22.6572(9) Å, b = 10.0205(4) Å, c = 4.9023(2) Å, V = 1113.01(8) Å3, Z = 5, Rgt(F) = 0.0341, wRref(F2) = 0.0857, T = 297 K.

CCDC no.: 2303765

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: Colorless needle
Size: 0.21 × 0.18 × 0.14 mm
Wavelength: MoKα radiation (0.71073 Å)
μ: 0.28 mm−1
Diffractometer, scan mode: ROD, Synergy Custom DW system
θmax, completeness: 26.3°, >99 %
N(hkl)measured, N(hkl)unique, Rint: 5529, 1998, 0.026
Criterion for Iobs, N(hkl)gt: Iobs > 2σ(Iobs), 1768
N(param)refined: 157
Programs: Olex2 [1], Shelx [2]
Table 2:

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

Atom x y z Uiso*/Ueq
C1 0.12996 (13) 0.6004 (3) 0.7664 (7) 0.0379 (7)
C2 0.09815 (13) 0.7174 (3) 0.7188 (6) 0.0378 (7)
C3 0.05407 (13) 0.7189 (3) 0.5180 (7) 0.0429 (8)
C4 0.04305 (13) 0.6061 (3) 0.3677 (7) 0.0455 (8)
H4 0.0135 0.6068 0.2361 0.055*
C5 0.07605 (14) 0.4900 (3) 0.4114 (8) 0.0469 (7)
H5 0.0689 0.4145 0.3064 0.056*
C6 0.11856 (14) 0.4873 (3) 0.6071 (8) 0.0440 (8)
H6 0.1402 0.4098 0.6353 0.053*
C7 −0.01873 (16) 0.8466 (4) 0.2824 (8) 0.0627 (11)
H7A −0.0006 0.8310 0.1084 0.094*
H7B −0.0361 0.9340 0.2844 0.094*
H7C −0.0488 0.7809 0.3134 0.094*
C8 0.17582 (13) 0.5952 (3) 0.9721 (7) 0.0393 (7)
H8 0.1951 0.5147 1.0024 0.047*
C9 0.23554 (13) 0.6852 (3) 1.3064 (7) 0.0402 (8)
C10 0.31278 (13) 0.6336 (3) 1.6205 (7) 0.0435 (7)
C11 0.35918 (15) 0.5776 (4) 1.7974 (8) 0.0584 (10)
H11A 0.3925 0.5521 1.6881 0.088*
H11B 0.3441 0.5006 1.8910 0.088*
H11C 0.3712 0.6434 1.9283 0.088*
N1 0.19088 (11) 0.6974 (2) 1.1146 (6) 0.0386 (6)
N2 0.25635 (13) 0.7905 (2) 1.4268 (7) 0.0537 (7)
N3 0.30113 (14) 0.7610 (3) 1.6066 (7) 0.0569 (8)
O1 0.02461 (11) 0.8376 (2) 0.4912 (5) 0.0587 (7)
O2 0.10777 (10) 0.8308 (2) 0.8615 (5) 0.0517 (7)
H2 0.1340 0.8180 0.9738 0.078*
S1 0.26903 (4) 0.53806 (7) 1.4100 (2) 0.0481 (3)

1 Experimental details

The structure was solved with Shelxt program and refined with the Shelxt refinement package under Olex2 suite [1, 2]. All hydrogen atoms were placed in calculated positions and refined as riding atoms, with Uiso(H) = 1.5Ueq(C) for methyl H and hydroxyl H atoms. Uiso(H) was set to 1.2Ueq(C) for all other H atoms.

2 Source of material

All chemicals were commercially sourced and were not further purified. Weigh 0.1152 g (1.0 mmol) of 2-amino-5-methyl-1,3,4-thiadiazole and 0.1522 g (1.0 mmol) of orthovanillin into a three necked flask containing 8.0 mL of anhydrous ethanol stirring at room temperature. In addition, add 1 mL of acetic acid as the catalyst and reflux at 80 °C for 2 h, and the solution turns yellow. The solution was filtered and then put into a Teflon-lined autoclave, and heated for three days at 80 °C, cooled to room temperature slowly and colorless needle crystals formed.

3 Comment

Schiff bases are a class of compounds formed by double bonding carbon atoms with nitrogen atoms [3], and their excellent coordination structure is due to the presence of C=N in the structure. The different structures and functional groups of reactants give Schiff bases different properties. Therefore, Schiff base compounds have important applications in multiple fields [4]. Schiff bases can be divided into salicylaldehydes, amino acids, acetamides, etc. according to the types of reactants [5]. Among them, salicylaldehydes Schiff bases are the most and earliest studied. They are a type of Schiff base obtained by condensation reaction between salicylaldehydes and amines, which is easy to prepare and has good biological activity, and is an oxygen-containing ligand. It have various coordination modes with different metal ions, providing conditions for the formation of highly biologically active Schiff base compounds [6].

From the data of bond length and bond angle of the title Schiff base compound, it can be seen that the C=N double bond length N1–C8 in Schiff base is 1.286(4) Å, which is longer than the average bond length of the usual C=N double bond [7, 8]. The bond length between the phenolic hydroxyl oxygen O1 in Schiff base and the carbon atom C3 on the benzene ring is 1.370(4) Å, which is between the C–O single bond and the C=O double bond [911]. And the bond length of C1–C8 is equal to 1.449(4) Å, which is 0.091 Å shorter than the typical C–C single bond (1.54 Å). Schiff base has intramolecular hydrogen bonds, where the phenolic hydroxyl O atom on orthovanillin forms an O2–H1⋯N1 hydrogen bond with the N atom in the Schiff base C=N double bond, forming a stable six-membered ring with C2, C1, and C8.


Corresponding author: Qiuchan Huang, College of Chemical and Biological Engineering, Guangxi Minzu Normal University, Chongzuo, Guangxi 532200, China, E-mail:

Funding source: The Guangxi Universities Research Foundation of Young and Middle-Aged Teachers Foundation

Award Identifier / Grant number: 2022KY0769

Award Identifier / Grant number: 2023KY0769

Award Identifier / Grant number: 2021KY0773

Funding source: Guangxi Minzu Normal University Foundation

Award Identifier / Grant number: 2023SBNGCC001

Award Identifier / Grant number: 2021YB038

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

  2. Research funding: Guangxi Universities Research Foundation of Young and Middle-Aged Teachers Foundation (2022KY0769, 2023KY0769 and 2021KY0773) and the Guangxi Minzu Normal University Foundation (2023SBNGCC001, 2021YB038).

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

References

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Received: 2023-10-06
Accepted: 2023-10-26
Published Online: 2023-11-21
Published in Print: 2024-02-26

© 2023 the author(s), published by De Gruyter, Berlin/Boston

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

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