Home The crystal structure of N′1,N′3-di((E)-benzylidene) isophthalohydrazide dihydrate, C 22 H 22 N 4 O 4
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The crystal structure of N1,N3-di((E)-benzylidene) isophthalohydrazide dihydrate, C 22 H 22 N 4 O 4

  • Ni Lai , Sheng-Ting Zhang , Fei Zou , Lin Yuan ORCID logo EMAIL logo and Zhong-Yan Li EMAIL logo
Published/Copyright: March 20, 2023

Abstract

C 22 H 22 N 4 O 4 , monoclinic, C2/c (no. 15), a = 34.315(13) Å, b = 6.701(3) Å, c = 9.105(3) Å, β =  98.510 ( 4 ) ° , V = 2070.7(13)  Å 3 , Z = 4, R g t (F) = 0.0461, w R r e f ( F 2 ) = 0.1413, T = 296(2) K.

CCDC no.: 2246750

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: 0.51 × 0.45 × 0.39 mm
Wavelength: Mo Kα radiation (0.71073 Å)
μ: 0.09 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: 9240, 1824, 0.027
Criterion for I obs, N(hkl)gt: I obs > 2σ(I obs), 1390
N(param)refined: 149
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 0.02778 (4) 0.0116 (2) 0.18142 (15) 0.0368 (4)
C2 0.02747 (5) −0.1952 (2) 0.1818 (2) 0.0515 (5)
H2 0.045704 −0.265788 0.136148 0.062*
C3 0.000000 −0.2959 (3) 0.250000 0.0645 (8)
H3 0.000000 −0.436 (6) 0.250000 0.094 (10)*
C4 0.000000 0.1126 (3) 0.250000 0.0390 (5)
H4 0.000000 0.261 (4) 0.250000 0.052 (7)*
C5 0.05656 (4) 0.1350 (2) 0.11193 (16) 0.0393 (4)
C6 0.13097 (5) 0.0466 (3) −0.10204 (18) 0.0477 (4)
H6 0.132503 −0.090757 −0.087861 0.057*
C7 0.15728 (5) 0.1438 (3) −0.19286 (19) 0.0487 (4)
C8 0.18771 (6) 0.0347 (3) −0.2392 (2) 0.0672 (6)
H8 0.191572 −0.097623 −0.209891 0.081*
C9 0.21231 (6) 0.1216 (4) −0.3287 (3) 0.0809 (7)
H9 0.232901 0.048056 −0.357335 0.097*
C10 0.20652 (7) 0.3145 (4) −0.3751 (3) 0.0801 (7)
H10 0.222996 0.371772 −0.435773 0.096*
C11 0.17610 (7) 0.4244 (3) −0.3315 (3) 0.0795 (7)
H11 0.171917 0.555291 −0.363945 0.095*
C12 0.15199 (6) 0.3404 (3) −0.2403 (2) 0.0643 (6)
H12 0.131903 0.416139 −0.209962 0.077*
N1 0.08100 (4) 0.03705 (19) 0.03306 (14) 0.0429 (4)
H1 0.081057 −0.091184 0.029501 0.052*
N2 0.10593 (4) 0.14748 (19) −0.04191 (14) 0.0443 (4)
O1 0.05818 (4) 0.31847 (16) 0.12824 (14) 0.0552 (4)
O2 0.08283 (4) −0.37552 (19) −0.06118 (17) 0.0609 (4)
H2A 0.0743 (7) −0.384 (4) −0.163 (3) 0.104 (9)*
H2B 0.0790 (7) −0.486 (5) −0.022 (3) 0.092 (8)*

1 Source of material

Isophthalohydrazide (10 mmol, 1.94 g) and benzaldehyde (20 mmol, 2.12 g) were dissolved in ethanol (15 mL) and the mixture was refluxed for 4 h and the resulting precipitate was collected by filtration and washed with ethanol. The product (0.5 g) was dissolved in ethanol (15 mL), and the crystals of the title compound were obtained by slow evaporation within 1 week.

2 Experimental details

All hydrogen atoms were identified in difference Fourier syntheses. The U i s o values of all hydrogen atoms were set to 1.2 U e q (C).

3 Comment

Aroylhydrazone compounds have rich biological activities, such as the treatment of tuberculosis, fungicidal activity and so on [4], [5], [6], [7]. Meanwhile, because of their strong coordination ability, aroylhydrazone compounds are often used for metal ion detection [8], [9], [10].

Herein, a novel aroylhydrazone compound was synthesized and characterized by single-crystal X-ray diffraction [1], [2], [3]. In the crystal, the molecule exhibits crystallographic twofold axial symmetry where C(3) and C(4) are located. The title molecule is the solvtomorph of the corresponding methanol containing compound [7]. The title molecule is non-planar and the dihedral angle between rings C1–C4 and C7–C12 is 18.4 ( 5 ) ° . The bond lengths of C(1)–C(5), C(5)–O(1), C(5)–N(1), N(1)–N(2), N(2)–C(6) and C(6)–C(7) are 1.4980(19), 1.2389(19), 1.3519(18), 1.3850(17), 1.278(2) and 1.464(2) respectively. The bond angles of C(1)–C(5)–O(1), O(1)–C(5)–N(1) and C(1)–C(5)–N(1) are 121.19 ( 13 ) ° , 121.67 ( 13 ) ° and 117.13 ( 13 ) ° [11]. In the crystal, the acyl hydrazone molecule and water molecule are connected by a hydrogen bond N(1)–H⋯O(2) (see the figure).


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: ,

Funding source: Natural Science Foundation of Hunan Province of China

Award Identifier / Grant number: 2021JJ30291

Funding source: Scientific Research Fund of Hunan Provincial Education Department

Award Identifier / Grant number: 21A0518

Award Identifier / Grant number: 21C0691

Funding source: National undergraduate training program for innovation and entrepreneurship

Award Identifier / Grant number: 202210551005X

Award Identifier / Grant number: 202210551011X

Funding source: Undergraduate Training Program for Innovation and Entrepreneurship of Hunan Province of China

Award Identifier / Grant number: [2022]174–4207

Award Identifier / Grant number: [2022]174–4213

Funding source: Yongzhou Guiding Science and Technology Plan Project

Award Identifier / Grant number: 2021

  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: 2023-02-08
Accepted: 2023-03-07
Published Online: 2023-03-20
Published in Print: 2023-06-27

© 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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