Journal of Structural Chemistry, Vol. 42, No. 2, pp. 335-339, 2001
Original Russian Text Copyright © 2001 by Yu. M. Chumakov, B. Ya. Antosyak, V. I. Tsapkov, and N. M. Samus
CRYSTAL STRUCTURE OF 5-CHLOROSALICYLIC
ALDEHYDE ISONICOTINOYL HYDRAZONE
UDC 548.736.547.574
Yu. M. Chumakov, B. Ya. Antosyak,
V. I. Tsapkov, and N. M. Samus
Isonicotinoyl hydrazide (tubazid) is the chief derivative of isonicotinic acid, possessing high bacteriostatic activity
against microbacteria of tuberculosis and used for treatment and localization of all forms of tuberculosis [1-3]. Recent
evolution of drug-resistant strains of this pathogen, however, calls for development of new bactericidal and bacteriostatic
pharmaceuticals. Among these are hydrazones (phthivazide, saluzide, etc.) [4-6], obtained by condensation of isonicotinoyl
hydrazide with substituted aromatic aldehydes. Therefore acquisition and systematization of experimental data on synthesis
and structure of this class of compounds is of both scientific and practical interest.
Here we report on the results of synthesis and X-ray diffraction study of 5-chlorosalicylic aldehyde isonicotinoyl
hydrazone (I).
. Azomethine I was prepared by boiling equimolar amounts of isonicotinoyl hydrazide and
Experimental. Synthesis
5-chlorosalicylic aldehyde. Recrystallization from ethanol gave light yellow crystals with t = 237-238°C (ν(NH) 3300,
m
3220, 3100; ν(C=O) 1660; ν(C=H) 1620; δ(N–H) 1570; δ(C–N) 1340; δ(OH) 1255, 1255, 1245; δ(NCH) 1240; ν(C–O)
−1
1180 cm ). Found, %: C 56.48, H 3.42, Cl 12.69, N 15.17. Calculated for C H ClN O , %: C 56.62, H 3.63, Cl 12.89,
13 10
3 2
N 15.25.
X-ray diffraction study. An X-ray diffraction experiment was carried out on a DAR-UMB diffractometer (MoK
α
radiation, graphite monochromator, room temperature, ω-θ/2θ scan mode). An absorption correction was not applied. The
structure was solved by direct methods using SHELX-86 software [7]. The least-squares refinement was performed with
SHELX-93 [8] anisotropically for nonhydrogen atoms and isotropically for hydrogens. The latter were placed geometrically
and refined as atoms rigidly bound with the respective nonhydrogen atoms. In the case of the hydroxyl group, the most
probable orientation of H atoms for the respective OH group was determined from difference Fourier maps and then refined
by the least-squares procedure.
Crystal data and refinement parameters for compound I are listed in Table 1. The atomic coordinates are presented
in Table 2, and the bond lengths and angles are given in Table 3.
TABLE 1. Experimental Information and Crystal and Refinement Data for I
1
2
Molecular formula
Mol. wt.
Temperature, K
Wavelength, Å
Crystal system
Space group
C H ClN O
13 10 3 2
275.69
293(2)
0.71073
Monoclinic
P2 /n
1
Cell parameters
a, Å
8.710(2)
b, Å
15.776(3)
Institute of Applied Physics, Moldavian Academy of Sciences, Kishinev. Moldavian State University, Kishinev.
Translated from Zhurnal Strukturnoi Khimii, Vol. 42, No. 2, pp. 400-404, March-April, 2001. Original article submitted
February 24, 2000.
©
0022-4766/01/4202-0335$25.00 2001 Plenum Publishing Corporation
335