Home Crystal structure of (E)-N′-(2-chloro-6-hydroxybenzylidene)-2-hydroxybenzohydrazide, C14H11ClN2O3
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Crystal structure of (E)-N′-(2-chloro-6-hydroxybenzylidene)-2-hydroxybenzohydrazide, C14H11ClN2O3

  • Jianlian Liu ORCID logo EMAIL logo , Hong Hao and Chaojun Du
Published/Copyright: June 18, 2021

Abstract

C14H11ClN2O3, monoclinic, P21/n (no. 14), a = 7.0242(11) Å, b = 25.375(4) Å, c = 7.6789(13) Å, β = 111.2752°, V = 1275.4(4) Å3, Z = 4, R gt (F) = 0.0349, wR ref (F 2) = 0.1123, T = 296(2) K.

CCDC no.: 2082667

The asymmetric unit of the title 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: 0.25 × 0.23 × 0.20 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: 6399, 2245, 0.023
Criterion for I obs, N(hkl)gt: I obs > 2 σ(I obs), 1909
N(param)refined: 183
Programs: Bruker [1], SHELX [2]
Table 2:

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

Atom x y z U iso*/U eq
C1 0.6707 (2) 0.32492 (6) 0.6496 (2) 0.0264 (4)
C2 0.6835 (2) 0.37973 (6) 0.6306 (2) 0.0311 (4)
C3 0.7307 (3) 0.41154 (7) 0.7874 (3) 0.0418 (4)
H3 0.743319 0.447752 0.776416 0.050*
C4 0.7590 (3) 0.38989 (8) 0.9589 (3) 0.0453 (5)
H4 0.790634 0.411732 1.062837 0.054*
C5 0.7414 (3) 0.33620 (8) 0.9798 (2) 0.0423 (4)
H5 0.758484 0.321968 1.096153 0.051*
C6 0.6979 (2) 0.30405 (6) 0.8250 (2) 0.0328 (4)
H6 0.686594 0.267871 0.837962 0.039*
C7 0.6280 (2) 0.29130 (6) 0.4830 (2) 0.0272 (3)
C8 0.7219 (2) 0.16077 (6) 0.4004 (2) 0.0290 (4)
H8 0.767364 0.149250 0.523688 0.035*
C9 0.7070 (2) 0.12389 (6) 0.2529 (2) 0.0272 (3)
C10 0.6617 (2) 0.14042 (6) 0.0664 (2) 0.0328 (4)
C11 0.6581 (3) 0.10471 (8) −0.0710 (3) 0.0442 (5)
H11 0.631030 0.116142 −0.192701 0.053*
C12 0.6948 (3) 0.05238 (8) −0.0267 (3) 0.0513 (5)
H12 0.691889 0.028650 −0.119913 0.062*
C13 0.7357 (3) 0.03403 (7) 0.1519 (3) 0.0462 (5)
H13 0.757917 −0.001654 0.179249 0.055*
C14 0.7429 (2) 0.06981 (6) 0.2892 (2) 0.0351 (4)
Cl1 0.79733 (9) 0.04664 (2) 0.51507 (7) 0.0589 (2)
N1 0.69976 (19) 0.24167 (5) 0.51329 (18) 0.0310 (3)
H1A 0.761624 0.230390 0.625330 0.037*
N2 0.6730 (2) 0.20921 (5) 0.36294 (18) 0.0300 (3)
O1 0.6557 (2) 0.40315 (5) 0.46567 (18) 0.0452 (3)
H1 0.618765 0.381112 0.381920 0.068*
O2 0.53252 (19) 0.30788 (4) 0.32239 (16) 0.0380 (3)
O3 0.6208 (2) 0.19117 (5) 0.01546 (18) 0.0471 (4)
H3A 0.631904 0.209004 0.107700 0.071*

Source of material

A mixture of 2-hydroxy-benzoic acid hydrazide (152.2 mg, 1 mmol) and 2-chloro-6-hydroxybenzaldehyde (156.6 mg, 1 mmol) in 50 mL anhydrous ethanol containing a few drops of glacial acetic acid was stirred under reflux conditions for 2 h. The mixture was cooled to room temperature and filtered, and then left at room temperature. After a few days, yellow block-shaped crystals suitable were obtained.

Experimental details

The hydrogen atoms were positioned geometrically (C–H = 0.93 Å, N–H = 0.86 Å, O–H = 0.82 Å) and refined as riding atoms. The U iso values were constrained to be 1.2U eq of the carrier atom for carbon bound H atoms and 1.5U eq for the remaining H atoms.

Comment

Halogenated Schiff bases are attracting more and more attention in several fields such as biochemistry, pharmacy, and coordination chemistry [3]. In addition, halogenated compounds containing the hydrazide moiety form intramolecular H-bonds [411]. In order to search for new Schiff bases containing halogen atoms, the title compound was synthesized and its crystal structure is reported here.

The asymmetric unit of the title compound consists of one formula unit (cf. the figure). The molecule exhibits an E configuration. The bond length of C8=N2 is 1.2804(19) Å exhibiting that the C8=N2 bond is a double bond. The two aromatic rings form the dihedral angle of 14.3°. The angle of C8=N2–N1 is 116.29(13)°, smaller than the ideal value of 120°. In the crystal packing, the chain structure was formed by intermolecular N–H…O hydrogen bonds. The intramolecular O–H…O and N–H…O hydrogen bonds also exist, which further consolidate the crystal.


Corresponding author: Jianlian Liu, School of Chemical Engineering, Northwest University, 710069, Xi’an, Shaanxi, People’s Republic of China; and School of Biological and Chemical Engineering, Nanyang Institute of Technology, 473004, Nanyang, Henan, People’s Republic of China, E-mail:

Funding source: Education Department of Henan Province

Award Identifier / Grant number: 20B530004

Funding source: Nanyang Science and Technology Bureau

Award Identifier / Grant number: JCQY004

Funding source: Nanyang Key Laboratory of Catalytic Functional Materials

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

  2. Research funding: Education Department of Henan Province (20B530004), Nanyang Science and Technology Bureau (JCQY004), and Nanyang Key Laboratory of Catalytic Functional Materials.

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

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Received: 2021-04-23
Accepted: 2021-05-10
Published Online: 2021-06-18
Published in Print: 2021-09-27

© 2021 Jianlian Liu et al., published by De Gruyter, Berlin/Boston

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

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