Home Crystal structure of (E)-N′-(1-(5-chloro-2-hydroxyphenyl)propylidene)-4-hydroxybenzohydrazide, C16H15ClN2O3
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Crystal structure of (E)-N′-(1-(5-chloro-2-hydroxyphenyl)propylidene)-4-hydroxybenzohydrazide, C16H15ClN2O3

  • Zhaoyan Li ORCID logo EMAIL logo
Published/Copyright: June 29, 2022

Abstract

C16H15ClN2O3, monoclinic, P21/c (no. 14), a = 4.9561(17) Å, b = 31.458(11) Å, c = 9.764(3) Å, β = 93.581(6)°, V = 1519.3(9) Å3, Z = 4, R gt(F) = 0.0497, wR ref (F 2) = 0.1359, T = 296(2) K.

CCDC no.: 2180380

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: Yellow block
Size: 0.23 × 0.20 × 0.18 mm
Wavelength: Mo Kα radiation (0.71073 Å)
μ: 0.27 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: 7703, 2668, 0.078
Criterion for I obs, N(hkl)gt: I obs > 2 σ(I obs), 1755
N(param)refined: 202
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 0.8395 (5) 0.34834 (7) 0.5772 (3) 0.0334 (6)
C2 1.0662 (5) 0.34204 (8) 0.6659 (3) 0.0420 (7)
H2 1.161883 0.365298 0.702201 0.050*
C3 1.1499 (5) 0.30127 (8) 0.7003 (3) 0.0390 (7)
H3 1.302646 0.297311 0.759166 0.047*
C4 1.0088 (5) 0.26629 (7) 0.6480 (3) 0.0308 (6)
C5 0.7878 (5) 0.27303 (8) 0.5552 (3) 0.0374 (7)
H5 0.695093 0.249792 0.516676 0.045*
C6 0.7042 (5) 0.31355 (8) 0.5195 (3) 0.0379 (6)
H6 0.557314 0.317516 0.456822 0.046*
C7 1.1040 (5) 0.22312 (7) 0.6899 (3) 0.0318 (6)
C8 0.8394 (5) 0.11986 (7) 0.6782 (2) 0.0313 (6)
C9 0.5988 (5) 0.12448 (8) 0.5771 (3) 0.0394 (7)
H9A 0.493241 0.149044 0.601123 0.047*
H9B 0.484729 0.099510 0.581022 0.047*
C10 0.6906 (7) 0.12974 (11) 0.4337 (3) 0.0696 (10)
H10A 0.804720 0.154318 0.430281 0.104*
H10B 0.535757 0.133272 0.370620 0.104*
H10C 0.789629 0.104962 0.408978 0.104*
C11 0.9374 (5) 0.07756 (7) 0.7264 (2) 0.0306 (6)
C12 1.1625 (5) 0.07328 (7) 0.8222 (3) 0.0347 (6)
C13 1.2427 (6) 0.03315 (8) 0.8680 (3) 0.0487 (8)
H13 1.387931 0.030803 0.932617 0.058*
C14 1.1134 (6) −0.00333 (8) 0.8207 (3) 0.0491 (8)
H14 1.169391 −0.029981 0.852448 0.059*
C15 0.8978 (6) 0.00097 (8) 0.7246 (3) 0.0459 (7)
C16 0.8107 (5) 0.04029 (8) 0.6784 (3) 0.0405 (7)
H16 0.664774 0.042065 0.614012 0.049*
Cl1 0.73066 (19) −0.04462 (2) 0.66223 (11) 0.0828 (4)
N1 0.9102 (4) 0.19243 (6) 0.6815 (2) 0.0356 (5)
H1A 0.747153 0.198099 0.651866 0.043*
N2 0.9851 (4) 0.15165 (6) 0.7225 (2) 0.0352 (5)
O1 0.7606 (4) 0.38922 (5) 0.5508 (2) 0.0500 (5)
H1 0.622706 0.389236 0.499860 0.075*
O2 1.3387 (3) 0.21498 (5) 0.7277 (2) 0.0474 (5)
O3 1.3061 (4) 0.10718 (5) 0.87114 (19) 0.0470 (5)
H3A 1.235335 0.129114 0.841096 0.070*

Source of material

A mixture of 4-hydroxybenzohydrazide (1 mmol, 152.2 mg), 1-(5-chloro-2-hydroxyphenyl)propan-1-one (184.6 mg, 1 mmol), a few drops of glacial acetic acid, and 20 mL anhydrous ethanol was refluxed. The resulting solution was cooled to room temperature, and then left undisturbed for about several days to form yellow block crystals.

Experimental details

All H atoms were placed in idealized calculated positions and refined as riding on their parent atoms.

Comment

The 4-hydroxybenzoyl hydrazones as an important class of schiff-bases are widely investigated in coordination chemistry because of their excellent coordination properties [3], [4], [5], [6], [7], [8], [9].

The asymmetric unit of the title compound consists of one formula unit (cf. the figure). In the title crystal structure, the acylhydrazone molecule is in a ketone form and adopts an E configuration at the C=N double bond. The bond length between C8 and N2 is 1.292(3) Å, which shows a typical C=N double bond [10]. The angle of C8=N2–N1 is 119.0(2)°. The dihedral angle between the two aromatic rings of 3.5° indicates that they are all almost parallel to each other. In the solid state, the molecules are linked into two-dimensional networks along the ac-plane by O–H⋯O and N–H⋯O hydrogen bonds. In addition, intramolecular O–H⋯N hydrogen bonds further contribute to the stability of the structure.


Corresponding author: Zhaoyan Li, School of Biological and Chemical Engineering, Nanyang Institute of Technology, 473004, Nanyang, Henan, P. R. China, E-mail:

  1. Author contributions: The author has accepted responsibility for the entire content of this submitted manuscript and approved submission.

  2. Research funding: This work was financial supported by Nanyang Institute of Technology.

  3. Conflict of interest statement: The author declares no conflicts of interest regarding this article.

References

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Received: 2022-05-20
Accepted: 2022-06-20
Published Online: 2022-06-29
Published in Print: 2022-10-26

© 2022 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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