BY 4.0 license Open Access Published by De Gruyter (O) October 27, 2021

Crystal structure of (E)-N′-(1-(3-chloro-4-fluorophenyl)ethylidene)-4-hydroxy – tetrahydrofuran (2/1), C17H16ClFN2O2.5

Xiaobo Bao and Chongchong Tian ORCID logo

Abstract

C17H16ClFN2O2.5, monoclinic, P21/n (no. 14), a = 7.4495(6) Å, b = 16.5328(13) Å, c = 12.8519(10) Å, β = 91.329(1)°, V = 1582.4(2) Å3, Z = 4, R gt (F) = 0.0508, wR ref (F2) = 0.1461, T = 100(2) K.

CCDC no.: 2115383

The asymmetric unit of 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: 0.20 × 0.18 × 0.16 mm
Wavelength: Mo Kα radiation (0.71073 Å)
μ: 0.27 mm−1
Diffractometer, scan mode: Bruker APEX-II, φ and ω
θmax, completeness: 26.4°, >99%
N(hkl)measured, N(hkl)unique, Rint: 8782, 3237, 0.022
Criterion for Iobs, N(hkl)gt: Iobs > 2 σ(Iobs), 2624
N(param)refined: 237
Programs: Bruker [1], Shelx [2]

Table 2:

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

Atom x y z Uiso*/Ueq
Cl1 0.55344 (10) 0.63151 (5) 0.78700 (5) 0.0423 (2)
F1 0.5455 (2) 0.78998 (10) 0.69029 (13) 0.0438 (4)
O1 −0.1736 (2) 0.09435 (10) 0.20902 (12) 0.0279 (4)
H1 −0.219102 0.112331 0.153256 0.042*
O2 0.1487 (2) 0.32791 (10) 0.55528 (12) 0.0293 (4)
N1 0.1437 (2) 0.41662 (11) 0.42123 (13) 0.0191 (4)
H1A 0.116154 0.425879 0.355346 0.023*
N2 0.2148 (2) 0.47762 (11) 0.48274 (14) 0.0197 (4)
C1 −0.1042 (3) 0.15635 (13) 0.26577 (17) 0.0207 (5)
C2 −0.0270 (3) 0.13840 (13) 0.36309 (17) 0.0224 (5)
H2 −0.023764 0.084036 0.386987 0.027*
C3 0.0447 (3) 0.19925 (14) 0.42473 (16) 0.0205 (5)
H3 0.095975 0.186292 0.491016 0.025*
C4 0.0429 (3) 0.27967 (13) 0.39108 (16) 0.0176 (4)
C5 −0.0332 (3) 0.29686 (13) 0.29291 (16) 0.0193 (4)
H5 −0.034472 0.351088 0.268440 0.023*
C6 −0.1064 (3) 0.23651 (14) 0.23100 (16) 0.0209 (5)
H6 −0.158302 0.249423 0.164845 0.025*
C7 0.1163 (3) 0.34238 (14) 0.46269 (16) 0.0190 (4)
C8 0.2414 (3) 0.54582 (13) 0.43718 (17) 0.0197 (4)
C9 0.3228 (3) 0.61075 (14) 0.50305 (18) 0.0216 (5)
C10 0.3919 (3) 0.59196 (15) 0.60253 (18) 0.0243 (5)
H10 0.387253 0.537916 0.627448 0.029*
C11 0.4667 (3) 0.65217 (16) 0.66434 (19) 0.0290 (5)
C12 0.4732 (3) 0.73120 (16) 0.6274 (2) 0.0324 (6)
C13 0.4071 (3) 0.75104 (16) 0.5310 (2) 0.0339 (6)
H13 0.413018 0.805227 0.506723 0.041*
C14 0.3307 (3) 0.69060 (15) 0.46843 (19) 0.0279 (5)
H14 0.283403 0.704025 0.401358 0.034*
C15 0.1943 (4) 0.56159 (15) 0.32441 (18) 0.0298 (5)
H15A 0.248853 0.519845 0.281186 0.045*
H15B 0.239913 0.614838 0.304429 0.045*
H15C 0.063570 0.560342 0.314241 0.045*
O3a −0.0523 (5) 0.5568 (2) 0.8940 (3) 0.0370 (9)
C18a −0.1628 (17) 0.5056 (13) 0.9545 (10) 0.047 (4)
H18Aa −0.183287 0.453327 0.918458 0.056*
H18Ba −0.280567 0.531462 0.965875 0.056*
C19a −0.0643 (11) 0.4924 (6) 1.0569 (7) 0.050 (2)
H19Aa −0.081681 0.436546 1.082702 0.060*
H19Ba −0.104242 0.531180 1.110242 0.060*
C20a 0.1302 (17) 0.5072 (15) 1.0287 (10) 0.053 (4)
H20Aa 0.182435 0.551886 1.070863 0.064*
H20Ba 0.203346 0.457936 1.040349 0.064*
C21a 0.1228 (10) 0.5292 (6) 0.9161 (7) 0.049 (2)
H21Aa 0.211363 0.572158 0.901545 0.059*
H21Ba 0.150242 0.481446 0.872774 0.059*

  1. aOccupancy: 0.5.

Source of material

A mixture of 2-hydroxy-benzoic acid hydrazide (152.2 mg, 1 mmol) and 1-(3-chloro-4-fluoro-phenyl)-ethanone (1 mmol, 172.6 mg) in 50 mL anhydrous ethanol with a few drops of glacial acetic acid was stirred under reflux conditions for 3 h. The solvent was removed under reduced pressure and the solid product was recrystallized from 15 mL tetrahydrofuran. Crystals were obtained after three days.

Experimental details

Hydrogen atoms were placed in idealized positions and constrained to ride on their parent atoms. The U iso values were set to be 1.5U eq of the carrier atom for methyl and oxygen H atoms and 1.2U eq for the remaining H atoms. The highest difference electron density peak is is almost 5–10% of a chlorine atom, representing a minor disorder at the Õ-position of the chloro-fluoro-phenyl moiety.

Comment

Schiff bases containing halogen atoms are attractive due to their higher biological activity [3], [4], [5], [6], [7], [8], [9].

The asymmetric unit of the title compound consists of one molecule of the organic target compound and half a molecule of tetrahydrofuran solvent located on a two-fold rotation axis (see the figure). Geometric parameters are all in the expected ranges [10]. The title compound shows an E configuration around the C8=N2 bond. In the crystal structure, the short distance d(N2–C8) = 1.288(3) Å has a value of a typical C=N double bond. The C8=N2–N1 angle of 116.15(18)°. The two aromatic rings are almost parallel to each other with the dihedral angle of 3.2°. In the crystal structure, the intermolecular O–H…O hydrogen bonds link the molecules into chains along the c-axis .


Corresponding author: Chongchong Tian, College of Pharmacy, Jiangsu Vocational College of Medicine, 224005, Yancheng, Jiangsu, People’s Republic of China, E-mail:

Funding source: Natural Science Foundation of the Jiangsu Higher Education Institutions of China

Award Identifier / Grant number: 18KJB320004

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

  2. Research funding: This work was financial supported by Natural Science Foundation of the Jiangsu Higher Education Institutions of China (18KJB320004).

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

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Received: 2021-09-14
Accepted: 2021-10-13
Published Online: 2021-10-27
Published in Print: 2021-12-20

© 2021 Xiaobo Bao and Chongchong Tian, published by De Gruyter, Berlin/Boston

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