, Volume 121, Issue 2-3, pp 129-139

Crystal structures and hydrogen bonding schemes in four benzamide derivatives (2-hydroxy-benzamide, 2-hydroxy-thiobenzamide, 2-hydroxy-N,N-dimethyl-benzamide, and 2-Hydroxy-N,N-dimethyl-thiobenzamide)

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Summary

2-Hydroxy-benzamide, C7H7NO2; monoclinic; I2/a-C 2h 6 ;a=12.901 (2),b=4.982 (1),c=20.987 (3) Å; β=91.50 (2)°;Z=8. 2-Hydroxy-thiobenzamide, C7H7NOS; monoclinic; P21/n-C 2h 5 ;a=13.508 (5),b=6.780 (2),c=15.878 (6) Å; β=93.74 (5)°;Z=8. 2-Hydroxy-N,N-dimethyl-benzamide, C9H11NO2; orthorhombic; Pbca-D 2h 15 ;a=11.752 (2),b=16.680 (3),c=9.079 (2) Å;Z=8. 2-Hydroxy-N,N-dimethyl-thiobenzamide, C9H11NOS; monoclinic; P21/c-C 2h 5 ;a=6.983 (1),b=11.652 (3),c=11.704 (3) Å; β=100.02 (2)°;Z=4. The crystal structures of these four compounds were determined (respectively refined: 2-hydroxy-benzamide) by single crystal X-ray data. The refinements of the structure parameters by least squares methods yielded in all casesR<0.056. The hydrogen atoms were located by means of difference Fourier summations. The O-H ... O distances are 2.513 (1) Å in 2-hydroxy-benzamide (intramolecular) and 2.625 (1) Å in 2-hydroxy-N,N-dimethyl-benzamide (intermolecular). The two O-H ... S distances in 2-hydroxy-thiobenzamide are 2.904 (2) Å and 2.918 (2) Å (intramolecular, two molecules in the asymmetric unit) and 3.228 (2) Å in 2-hydroxy-N,N-dimethyl-thiobenzamide (intermolecular). Clear N-H ... O hydrogen bonds with 2.926 (1) Å and 3.006 (1) Å occur only in the structure of 2-hydroxy-benzamide (intermolecular).

Zusammenfassung

2-Hydroxy-benzamid, C7H7NO2; monoklin; I2/a-C 2h 6 ;a=12.901 (2),b=4.982 (1),c=20.987 (3) Å; β=91.50 (2)°;Z=8. 2-Hydroxy-thiobenzamid, C7H7NOS; monoklin; P21/n-C 2h 5 ;a=13.508 (5),b=6.780 (2),c=15.878 (6) Å; β=93.74 (5)°;Z=8. 2-Hydroxy-N,N-dimethyl-benzamid, C9H11NO2; orthorhombisch; Pbca-D 2h 15 ;a=11.752 (2),b=16.680 (3),c=9.079 (2) Å;Z=8. 2-Hydroxy-N,N-dimethyl-thiobenzamid, C9H11NOS; monoklin; P21/c-C 2h 5 ;a=6.983 (1),b=11.652 (3),c=11.704 (3) Å; β=100.02 (2)°;Z=4. Die Kristallstrukturen dieser vier Verbindungen wurden mittels Röntgen-Einkristalldaten bestimmt (bzw. verfeinert: 2-Hydroxy-benzamid). Die Verfeinerungen der Strukturparameter nach der Methode der kleinsten Quadrate ergab in allen FällenR<0.056. Die Wasserstoffatome konnten anhand von Differenz-Fourier-Summationen belegt werden. Die O-H ... O-Abstände haben folgende Werte: 2.513(1)Å in 2-Hydroxy-benzamid (intramolekular) und 2.625(1) Å in 2-Hydroxy-N,N-dimethyl-benzamid (intermolekular). Die zwei O-H ... S-Abstände sind in 2-Hydroxy-thiobenzamid 2.904(2)Å und 2.918(2)Å (intramolekular, zwei moleküle in der asymmetrischen Einheit) und 3.228(2)Å in 2-Hydroxy-N,N-dimethyl-thiobenzamid(intermollekular). Klar zuzuordnende N-H ... O-Wasserstoffbrücken mit 2.926(1)Å und 3.006(1)Å treten lediglich in der Struktur des 2-Hydroxy-benzamid auf (intermolekular).