Home The crystal structure of (E)-4-fluoro-N′-(1-(o-tolyl)ethylidene)benzohydrazide, C16H15FN2O
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The crystal structure of (E)-4-fluoro-N′-(1-(o-tolyl)ethylidene)benzohydrazide, C16H15FN2O

  • Chuyi Wang , Xiaojing Dai , Guojun Tang , Wei Wang ORCID logo EMAIL logo and Yang Zhao
Published/Copyright: February 23, 2024

Abstract

C16H15FN2O, monoclinic, Pc (no. 7), a = 12.3610(11) Å, b = 15.1269(17) Å, c = 8.1382(6) Å, β = 106.411(9)°, V = 1459.7(2) Å3, Z = 4, R gt (F) = 0.0565, wR ref (F 2) = 0.1315, T = 293 K.

CCDC no.: 2330946

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: 0.42 × 0.38 × 0.33 mm
Wavelength: Mo Kα radiation (0.71073 Å)
μ: 0.09 mm−1
Diffractometer, scan mode: SuperNova, ω
θ max, completeness: 29.3°, >99 %
N(hkl)measured, N(hkl)unique, R int: 12,312, 5772, 0.024
Criterion for I obs, N(hkl)gt: I obs > 2σ(I obs), 3966
N(param)refined: 365
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 U iso*/U eq
F1 0.0349 (2) 0.6781 (3) −0.3906 (4) 0.1095 (11)
F2 0.9653 (3) −0.1591 (4) 0.9521 (5) 0.1581 (18)
O1 0.3686 (3) 0.5823 (2) 0.3206 (3) 0.0677 (8)
O2 0.5830 (2) −0.1018 (2) 0.2715 (3) 0.0634 (8)
N1 0.4556 (3) 0.5101 (2) 0.1501 (4) 0.0565 (9)
H1 0.452821 0.491639 0.049060 0.068*
N2 0.5438 (3) 0.4877 (3) 0.2906 (4) 0.0570 (9)
N3 0.5337 (3) 0.0074 (2) 0.4245 (3) 0.0539 (8)
H3A 0.539566 0.031121 0.522577 0.065*
N4 0.4568 (3) 0.0376 (2) 0.2760 (3) 0.0507 (8)
C1 0.1190 (4) 0.6507 (3) −0.2528 (6) 0.0705 (13)
C2 0.0923 (4) 0.6297 (4) −0.1073 (6) 0.0788 (14)
H2 0.018501 0.634645 −0.101548 0.095*
C3 0.1764 (4) 0.6011 (3) 0.0312 (5) 0.0689 (12)
H3 0.159730 0.586959 0.132554 0.083*
C4 0.2851 (3) 0.5930 (3) 0.0217 (4) 0.0528 (10)
C5 0.3090 (4) 0.6156 (3) −0.1290 (5) 0.0595 (10)
H5 0.382444 0.611237 −0.136514 0.071*
C6 0.2237 (4) 0.6449 (3) −0.2689 (5) 0.0708 (13)
H6 0.238793 0.659953 −0.371019 0.085*
C7 0.3735 (3) 0.5625 (3) 0.1779 (5) 0.0534 (10)
C8 0.6033 (3) 0.4220 (3) 0.2778 (5) 0.0562 (11)
C9 0.5839 (6) 0.3638 (4) 0.1235 (7) 0.102 (2)
H9A 0.507178 0.343550 0.090546 0.152*
H9B 0.633802 0.313873 0.150107 0.152*
H9C 0.598340 0.396558 0.030888 0.152*
C10 0.7043 (4) 0.4045 (3) 0.4279 (5) 0.0621 (12)
C11 0.7880 (4) 0.4677 (4) 0.4673 (6) 0.0825 (15)
H11 0.778559 0.520050 0.404845 0.099*
C12 0.8850 (5) 0.4545 (6) 0.5973 (8) 0.108 (2)
H12 0.941603 0.497016 0.622900 0.130*
C13 0.8965 (6) 0.3786 (7) 0.6873 (7) 0.109 (2)
H13 0.962311 0.369278 0.775290 0.131*
C14 0.8165 (6) 0.3163 (6) 0.6544 (8) 0.113 (2)
H14 0.827163 0.264983 0.720075 0.136*
C15 0.7164 (5) 0.3276 (4) 0.5212 (7) 0.0872 (16)
C16 0.6244 (7) 0.2584 (5) 0.4860 (11) 0.147 (3)
H16A 0.566605 0.276430 0.536613 0.221*
H16B 0.655661 0.202981 0.534432 0.221*
H16C 0.592652 0.251895 0.364522 0.221*
C17 0.8749 (5) −0.1344 (6) 0.8192 (8) 0.100 (2)
C18 0.8265 (5) −0.1956 (5) 0.7016 (10) 0.113 (2)
H18 0.852992 −0.253459 0.709692 0.135*
C19 0.7353 (4) −0.1688 (4) 0.5673 (7) 0.0809 (14)
H19 0.701079 −0.209114 0.482176 0.097*
C20 0.6954 (3) −0.0846 (3) 0.5587 (5) 0.0548 (10)
C21 0.7501 (4) −0.0231 (4) 0.6789 (5) 0.0753 (14)
H21 0.725473 0.035270 0.670888 0.090*
C22 0.8418 (4) −0.0492 (5) 0.8116 (6) 0.0929 (18)
H22 0.879906 −0.008816 0.893778 0.112*
C23 0.5981 (3) −0.0606 (3) 0.4065 (4) 0.0499 (9)
C24 0.3779 (3) 0.0884 (3) 0.2899 (4) 0.0496 (9)
C25 0.3566 (4) 0.1193 (3) 0.4528 (5) 0.0713 (13)
H25A 0.344015 0.069094 0.517186 0.107*
H25B 0.291364 0.156794 0.426409 0.107*
H25C 0.420934 0.151711 0.519132 0.107*
C26 0.3053 (4) 0.1236 (3) 0.1234 (4) 0.0551 (10)
C27 0.1896 (4) 0.1141 (3) 0.0724 (6) 0.0717 (13)
C28 0.1294 (5) 0.0638 (5) 0.1748 (8) 0.121 (2)
H28A 0.159096 0.004808 0.192855 0.182*
H28B 0.050496 0.061437 0.114779 0.182*
H28C 0.139373 0.092333 0.283457 0.182*
C29 0.1307 (5) 0.1511 (4) −0.0856 (7) 0.0897 (17)
H29 0.052601 0.145751 −0.122145 0.108*
C30 0.1823 (6) 0.1934 (4) −0.1848 (6) 0.0918 (18)
H30 0.139721 0.217234 −0.288190 0.110*
C31 0.2972 (6) 0.2026 (3) −0.1375 (6) 0.0894 (16)
H31 0.332722 0.232378 −0.207820 0.107*
C32 0.3594 (4) 0.1670 (3) 0.0164 (5) 0.0663 (12)
H32 0.437610 0.171866 0.049224 0.080*

1 Source of materials

A 50 mL round-bottom flask, equipped with a stirring bar and a rubber membrane, was prepared. Then 1 mmol 4-fluorobenzoyl hydrazine and 1 mmol 2′-methylacetophenone were mixed with 3 drops of ice-cold acetic acid to serve as the starting materials for the reaction. Subsequently, 25 mL of anhydrous alcohol was added to the mixture, and stirring was performed at room temperature for 10 min to facilitate the reaction progress. The mixture was continuously stirred and maintained at 50 °C for 5 h to ensure completion of the desired reaction. To obtain the crude product, solvent evaporation was carried out using a rotary evaporator until complete dryness, leaving behind the solid product. The crude product was dissolved in a minimum quantity of hot ethanol under controlled heating conditions to ensure complete dissolution. Then, during the cooling and volatilization process of ethanol, the formation of crystals of the targeted compound was observed.

2 Experimental details

The obtained diffraction data were processed using the SHELXT software [2] to solve the crystal structure, which was further refined using full-matrix least-squares procedures in SHELXL [3]. Anisotropic refinement was applied to non-hydrogen atoms, while hydrogen atoms were refined isotropically. The resulting crystal structure was visually represented using the OLEX2 [4] and VESTA [5] software package.

3 Comment

Hydrazine derivatives have evoked a profound interest due to their diverse biological activities, making them promising candidates for the development of highly effective anti-infective agents [6]. The precise determination of crystal structures for hydrazine derivatives holds pivotal importance in the pursuit of novel drug discovery. A considerable number of crystal structures of hydrazine derivatives have been successfully elucidated and reported in the existing scientific literature [715]. In this study, we present the crystal structure of a novel hydrazine derivative, namely (E)-4-fluoro-N′-(1-(o-tolyl)ethylidene)benzohydrazide, and engage in a thorough structural discussion. These findings provide substantial support for the development of innovative pharmaceutical agents.

In the compound delineated in the title, a 4-fluorophenyl moiety replaces a hydrogen atom on the acyl carbon, resulting in the fluorine atom. Furthermore, in the molecular structure, the substituents on both sides of the C=N double bond adopt an configuration, wherein the larger substituent resides on either side of the double bond to facilitate favorable spatial orientation. The two phenyl rings exhibit discernible torsion, with a dihedral angle of 45°, akin to comparable crystal structures documented in previous literature [1620].

The molecules within the crystal lattice are arranged in a stacked manner along the c-axis direction. Significantly, no conspicuous intermolecular hydrogen bonding or ππ interactions are detected. The molecular arrangement within the crystal primarily stems from the maximization of spatial utilization.


Corresponding author: Wei Wang, Ningbo Key Laboratory of Agricultural Germplasm Resources Mining and Environmental Regulation, College of Science and Technology, Ningbo University, Zhejiang, China, E-mail:

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

  2. Competing interests: The authors declare no conflicts of interest regarding this article.

  3. Research funding: Scientific Research Fund of Ningbo City (Grant No.: 2023J173); National College Students’ Innovation and Entrepreneurship Training Program, China (No. 202313277012). Contract grant sponsors: K. C. Wong Magna Fund and HuLan Outstanding Doctor Fund in Ningbo University.

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Received: 2023-12-12
Accepted: 2024-02-05
Published Online: 2024-02-23
Published in Print: 2024-06-25

© 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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  59. Crystal structure of N-(1-(3,4-dimethoxyphenyl)-2-methylpropyl)aniline, C18H23NO2
  60. Crystal structure of Ba6Cd12Mn4SiF48
  61. Synthesis and crystal structure of 5-fluoro-1-methyl-2-oxo-3-(2-oxochroman-4-yl)indolin-3-yl acetate, C20H16FNO5
  62. The crystal structure of 6-methacryloylbenzo[d][1,3]dioxol-5-yl 4-nitrobenzenesulfonate, C17H13NO8S
  63. Crystal structure of ethyl 2-(3-benzyl-4-oxo-3,4-dihydrophthalazin-1-yl)- 2,2-difluoroacetate, C19H16F2N2O3
  64. The crystal structure of tetrakis(μ 2-(1H-benzimidazole-2-methoxo-κ2 N,O:O:O)-(n-butanol-κO)-chlorido)-tetranickel(II), C48H68Cl4N8O8Ni4
  65. Synthesis and crystal structure of trans-tetraaqua-bis((1-((7-hydroxy-3-(4-methoxy-3-sulfonatophenyl)-4-oxo-4H-chromen-8-yl)methyl)piperidin-1-ium-4-carbonyl)oxy-κO)zinc(II)hexahydrate, C46H64N2O28S2Zn
  66. The crystal structure of 1-(4-carboxybutyl)-3-methyl-1H-imidazol-3-ium hexafluoridophosphate, C9H15F6N2O2P
  67. Crystal structure of 1-(4-chlorophenyl)-4-(2-furoyl)-3-phenyl-1H-pyrazol-5-ol, C20H13ClN2O3
  68. Crystal structure of dimethyl (R)-2-(3-(1-phenylethyl)thioureido)-[1,1′-biphenyl]-4,4′-dicarboxylate, C25H24N2O4S
  69. The crystal structure of 1-(3-carboxypropyl)-1H-imidazole-3-oxide, C7H10N2O3
  70. Synthesis and crystal structure of dimethyl 4,4′-(propane-1,3-diylbis(oxy))dibenzoate, C19H20O6
  71. Crystal structure of methyl-1-(p-tolyl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylate, C20H20N2O2
  72. The crystal structure of 1-(1-adamantan-1-yl)ethyl-3-(3-methoxyphenyl)thiourea, C20H28N2OS
  73. The crystal structure of N,N′-carbonylbis(2,6-difluorobenzamide), C15H8F4N2O3
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