Home The crystal structure of (E)-4-amino-N′-(1-(4-fluorophenyl)propylidene)benzohydrazide, C16H16FN3O
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The crystal structure of (E)-4-amino-N′-(1-(4-fluorophenyl)propylidene)benzohydrazide, C16H16FN3O

  • Jianqiang Cui , Yahuan Yuwen , Meimei Zhao and Bin Liu ORCID logo EMAIL logo
Published/Copyright: February 6, 2024

Abstract

C16H16FN3O, orthorhombic, Pbca (no. 61), a = 12.5936(10) Å, b = 7.7308(9) Å, c = 29.568(3) Å, V = 2878.7(5) Å3, Z = 8, Rgt(F) = 0.0872, wR ref (F2) = 0.1893, T = 293 K.

CCDC no.: 2326065

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: Colourless block
Size: 0.46 × 0.38 × 0.31 mm
Wavelength: Mo Kα radiation (0.71073 Å)
μ: 0.09 mm−1
Diffractometer, scan mode: SuperNova, ω
θmax, completeness: 29.1°, >99 %
N(hkl)measured, N(hkl)unique, Rint: 10,068, 3345, 0.046
Criterion for Iobs, N(hkl)gt: Iobs > 2σ(Iobs), 1870
N(param)refined: 192
Programs: Bruker [1], SHELX [2], [3], Olex2 [4]
Table 2:

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

Atom x y z Uiso*/Ueq
F1 0.33490 (19) 0.0102 (3) 0.60032 (7) 0.0838 (7)
O1 0.08465 (18) 0.2963 (4) 0.35338 (8) 0.0730 (8)
N1 0.1478 (2) 0.7258 (5) 0.17172 (9) 0.0739 (10)
H1A 0.199532 0.688745 0.155122 0.089*
H1B 0.088463 0.703150 0.158303 0.089*
N2 0.2473 (2) 0.4070 (3) 0.36772 (8) 0.0492 (7)
H2 0.299115 0.471114 0.358925 0.059*
N3 0.2524 (2) 0.3209 (3) 0.40856 (8) 0.0490 (7)
C1 0.1520 (2) 0.6445 (4) 0.21330 (10) 0.0483 (8)
C2 0.2485 (2) 0.6062 (5) 0.23368 (10) 0.0564 (9)
H2A 0.311557 0.634849 0.219103 0.068*
C3 0.2517 (2) 0.5263 (4) 0.27524 (10) 0.0508 (9)
H3 0.317246 0.501212 0.288202 0.061*
C4 0.1599 (2) 0.4823 (4) 0.29822 (10) 0.0410 (7)
C5 0.0637 (2) 0.5199 (5) 0.27737 (10) 0.0517 (9)
H5 0.000710 0.490012 0.291793 0.062*
C6 0.0595 (2) 0.6001 (5) 0.23604 (10) 0.0536 (9)
H6 −0.006070 0.624990 0.223107 0.064*
C7 0.1588 (2) 0.3891 (4) 0.34149 (11) 0.0477 (8)
C8 0.3394 (2) 0.3380 (4) 0.43131 (10) 0.0421 (7)
C9 0.4344 (2) 0.4372 (5) 0.41529 (11) 0.0556 (9)
H9A 0.479404 0.463822 0.441001 0.067*
H9B 0.411058 0.545816 0.402213 0.067*
C10 0.4992 (3) 0.3381 (6) 0.38027 (13) 0.0853 (13)
H10A 0.455147 0.311835 0.354663 0.128*
H10B 0.524802 0.232423 0.393390 0.128*
H10C 0.558252 0.407441 0.370716 0.128*
C11 0.3403 (2) 0.2490 (4) 0.47574 (10) 0.0421 (7)
C12 0.4326 (3) 0.2249 (5) 0.50035 (11) 0.0572 (9)
H12 0.496848 0.263047 0.488454 0.069*
C13 0.4314 (3) 0.1448 (5) 0.54256 (12) 0.0639 (10)
H13 0.493723 0.128966 0.558896 0.077*
C14 0.3367 (3) 0.0907 (5) 0.55914 (11) 0.0575 (9)
C15 0.2445 (3) 0.1094 (5) 0.53635 (11) 0.0616 (10)
H15 0.181014 0.068901 0.548469 0.074*
C16 0.2463 (3) 0.1896 (4) 0.49494 (10) 0.0544 (9)
H16 0.182967 0.204596 0.479280 0.065*

1 Source of materials

In a 50 mL round-bottom flask equipped with a stopper, 1 mmol of 4-aminobenzohydrazide and 1 mmol of 4′-fluoropropiophenone were added, along with 25 mL of anhydrous ethanol. The mixture was stirred at room temperature for 10 min. Subsequently, 3 drops of concentrated acetic acid were added, and the mixture was heated to 50 °C with stirring for 3 h. The solvent was evaporated using a rotary evaporator to obtain the crude product. Afterwards, 80 mg of the crude product was dissolved in a solvent mixture of ethanol and water (v:v = 3:1). Once dissolved, the system was left open at room temperature, allowing the solvent to evaporate. During the evaporation process, the formation of crystalline particles was observed.

2 Experimental details

The C–H bond distances were constrained to be between 0.90 and 0.97 Å with an isotropic displacement parameter (Uiso) of 1.5 times the equivalent isotropic displacement parameter (Ueq) of carbon for methyl hydrogen atoms, and 1.2 times Ueq(C) for all other hydrogen atoms.

3 Comment

Acylhydrazine is a derivative of hydrazine obtained through acylation. Its pharmacological activities, including anti-inflammatory, anti-tumor, and anti-tuberculosis properties [5]. This is attributed to the presence of the methyleneimino group (–NH–N=CH–) connected to the carbonyl group [6], [7], [8], [9], and many similar crystal structures were reported [10], [11], [12], [13]. This article presents the crystal structure of (E)-4-amino-N′-(1-(4-fluorophenyl)propylidene)benzohydrazide, belonging to the acylhydrazine derivative class.

In the title compound, the dihedral angle between the planes of the 4-fluorophenyl and 4-aminophenyl rings is 7.3°. These rings make dihedral angles of 32.4° and 25.1°, respectively, with the central hydrazide group.


Corresponding author: Bin Liu, Xianyang Key Laboratory of Molecular Imaging and Drug Synthesis, School of Higher Vocational, Shaanxi Institute of International Trade & Commerce, Xianyang, Shaanxi, China, E-mail:

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

  2. Research funding: Projects of Natural Science Foundation of Shaanxi Province (2021JM-561), Key Laboratory of Molecular Imaging and Drug Synthesis of Xianyang City (2021QXNL–PT-0008) and effective substances of traditional Chinese medicine innovative team in Shaanxi institute of international trade & commerce (SSY18TD01).

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

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Received: 2023-12-13
Accepted: 2024-01-17
Published Online: 2024-02-06
Published in Print: 2024-04-25

© 2024 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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