Home The crystal structure of N′1,N′3-bis((E)-thiophen-2-ylmethylene)isophthalohydrazide monohydrate, C18H16N4O3S2
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The crystal structure of N1,N3-bis((E)-thiophen-2-ylmethylene)isophthalohydrazide monohydrate, C18H16N4O3S2

  • Zi-Yi Yin , Fei Zou , Jue-Yuan Chen , Lin Yuan EMAIL logo and Zhong-Yan Li EMAIL logo
Published/Copyright: May 9, 2023

Abstract

C18H16N4O3S2, monoclinic, C2/c (no. 15), a = 19.694(4) Å, b = 11.450(2) Å, c = 8.3382(16) Å, β =  91.820 ( 2 ) , V = 1879.3(6) Å3, Z = 4, R g t (F) = 0.0408, w R r e f (F 2) = 0.1206, T = 296(2) K.

CCDC no.: 2259827

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: Block
Size: 0.42 × 0.39 × 0.31 mm
Wavelength: Mo Kα radiation (0.71073 Å)
μ: 0.31 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: 8713, 1649, 0.015
Criterion for I obs, N(hkl)gt: I obs > 2σ(I obs), 1489
N(param)refined: 127
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 0.46045 (8) 0.66797 (14) 0.63606 (18) 0.0377 (4)
C2 0.46145 (9) 0.78919 (17) 0.6358 (2) 0.0470 (4)
H2 0.436088 0.830127 0.558403 0.056*
C3 0.500000 0.8494 (2) 0.750000 0.0535 (7)
H3 0.499999 0.930580 0.750001 0.064*
C4 0.500000 0.6073 (2) 0.750000 0.0356 (5)
H4 0.499999 0.526108 0.750001 0.043*
C5 0.41976 (8) 0.60213 (15) 0.51155 (18) 0.0392 (4)
C6 0.35943 (9) 0.31999 (17) 0.4990 (2) 0.0466 (4)
H6 0.377051 0.301597 0.600649 0.056*
C7 0.32880 (10) 0.22840 (17) 0.4024 (2) 0.0488 (5)
C8 0.33478 (14) 0.1118 (2) 0.4330 (3) 0.0723 (7)
H8 0.358641 0.081174 0.521367 0.087*
C9 0.30095 (17) 0.0431 (3) 0.3164 (4) 0.0940 (10)
H9 0.300422 −0.038114 0.318823 0.113*
C10 0.26960 (14) 0.1061 (3) 0.2015 (3) 0.0824 (8)
H10 0.244392 0.074101 0.116097 0.099*
N1 0.39507 (7) 0.49969 (13) 0.56020 (15) 0.0433 (4)
H1 0.398906 0.480115 0.659652 0.052*
N2 0.36323 (7) 0.42481 (13) 0.45023 (16) 0.0432 (4)
O1 0.41189 (7) 0.63889 (12) 0.37323 (14) 0.0541 (4)
O2 0.500000 1.1683 (4) 0.750000 0.1592 (19)
H2A 0.503396 1.228051 0.690264 0.239*
H2B 0.463308 1.172206 0.800742 0.239*
S1 0.28134 (3) 0.25195 (5) 0.23017 (7) 0.0639 (3)

1 Source of material

Isophthalohydrazide (194 mg, 1 mmol) and thiophene-2-carbaldehyde (224 mg, 2 mmol) were dissolved in ethanol (15 mL) and the mixture was refluxed for 6 h. The target compound (351 mg, yield 92 %) was collected by filtration and washed with ethanol. Single crystals of the product can be obtained by recrystallization from ethanol.

2 Experimental details

All hydrogen atoms were identified in difference Fourier syntheses. The U iso values of the methyl groups, phenolic hydroxyl and water were set to 1.5U eq (C), and the U iso values of all other hydrogen atoms were set to 1.2U eq (C).

3 Comment

Hydrazone is a Schiff base constructed by hydrazide and carbonyl compounds. It has attracted much attention due to its biological activities [4,5]. The structure of hydrazone compounds has always been the focus of research [6], [7], [8], [9], [10], [11].

A compound containing thiophene ring was synthesized from isophthalohydrazide with thiophene-2-carbaldehyde and characterized by single-crystal X-ray diffraction [1], [2], [3]. In the crystal, the molecule exhibits crystallographic C2 axial symmetry (C3, C4 and O2). The title molecule is V-shaped. The dihedral angle between rings C1–C4 and C7–S1 is 5.6°, and the dihedral angle between rings C7–S1 and C7-a–S1-a is 3 . 7 . The bond lengths of C(1)–C(5), C(5)–N(1), N(1)–N(2), N(2)–C(6), C(6)–C(7), C(7)–S(1) and S(1)–C(10) are 1.338(2), 1.3902(19), 1.270(2), 1.443(3), 1.710(2) and 1.702(3) Å respectively.


Corresponding authors: Lin Yuan and Zhong-Yan Li, College of Chemistry and Bioengineering, Hunan University of Science and Engineering, Yongzhou, Hunan 425199, P.R. China, E-mail: ,

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

  2. Research funding: Natural Science Foundation of Hunan Province of China (2021JJ30291), the Scientific Research Fund of Hunan Provincial Education Department (21A0518, 21C0691), National undergraduate training program for innovation and entrepreneurship (202210551005X, 202210551011X), Undergraduate Training Program for Innovation and Entrepreneurship of Hunan Province of China ([2022]174-4207, [2022]174-4213), Yongzhou Guiding Science and Technology Plan Project (2021).

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

References

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Received: 2023-04-09
Accepted: 2023-04-29
Published Online: 2023-05-09
Published in Print: 2023-08-28

© 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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