Abstract
Both 5-amino-1-(2-hydroxyethyl)imidazole-4-carboxamide (AHIC) and 5-amino-1-(2-chloroethyl)-4-cyanoimidazole (ACCI) have been synthesized and crystallized in the monoclinic space group P21/c, Z = 4, with a = 8.420(2), b = 9.759(2), c = 10.583(2) Å, β = 111.80(2)° for AHIC and a = 6.139(1), b = 8.522(2), c = 15.156(3) Å, β = 96.71(2)° for ACCI. Differences in the molecular geometries of the two compounds are attributed to the differences in the substituents at the 1- and 4-positions of the imidazole ring. The molecular conformation of AHIC is stabilized by intramolecular hydrogen bonding between the 5-amino and the vicinal carboxamide moiety, resulting in an extended planar structural pattern. The presence of the cyano group in the 4-position of ACCI prevents the formation of such an intramolecular hydrogen bond. Both the crystal structures are stabilized by networks of intermolecular hydrogen bonds.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
Lunt, E. Progress in Pharmaceutical Research; Woolridge, K.R.H., Ed.; Blackwell Scientific Publication: Oxford, 1982; Vol. 4.
Ford, R.E.; Knowles, P.; Lunt, E.; Marshall, S.M.; Penrose, A.J.; Ramsden, C.A.; Summers, A.J.H.; Walker, J.L.; Wright, D.E. J. Med. Chem. 1986, 29, 538.
Sen, A.K.; Ray, S. Indian J. Chem. 1976, 14B, 346.
Fan Hai-Fu. SAP191—Structure Analysis Programs with Intelligent Control; Rigaku Corporation: Tokyo, Japan, 1991.
Beurskens, P.T. DIRDIF—Direct Methods for Difference Structures—An Automated Procedure for Phase Extension and Refinement of Difference Structure Factors: Technical Report 1984/1; Crystallography Laboratory: Nijmengen, Netherlands, 1984.
TEXAN: Crystal Structure Analysis Package; Molecular Structure Corporation, 1985 & 1992.
Cromer, D.T.; Waber, J.T. The International Tables for XRay Crystallography; Kynoch Press: Birmingham, England (Present distributor: Kluwer Academic Publisher: Dordrecht), 1974; Vol. IV, Table 2.2A.
Creagh, D.C.; McAuley, W.J. The International Tables for XRay Crystallography; Kluwer Academic Publishers: Boston, 1992; Vol. C, Table 4.2.6.8.
Nardelli, M. Comput. Chem. 1983, 7, 95.
Johnson, C.K. ORTEPII, Report ORNL-5138; Oak Ridge National Laboratory: TN, 1976.
Adamaik, D.A.; Saenger, W. Acta Crystallogr. 1979, B35, 924.
Kalman, S.; Jozsef, S.; Kalman, A. Acta Crystallogr. 1980, B36, 2323.
Banerjee, T.; Roychowdhury, P.; Chattopadhyay, D.; Ray, S.; Chatterjee, G.; Kashino, S.; Haisa, M. Acta Crystallogr. 1991, C47, 804.
Bracuti, A.J. J. Chem. Crystallogr. 1995, 25, 625.
De Bondt, H.L.; Ragia, E., Blaton N.M.; Peeters, O.M.; De Ranter, C.J. Acta Crystallogr. 1993, C49, 693.
Banerjee, T.; Roychowdhury, P.; Yamane, T.; Ray, S.; Pathak, K. -J. Cryst. Spectosc. Res. 1991, 21, 121.
Afshar, C.; Berman, H.M.; Sawzic, P. Lessinger, L.; Lim, B.B.; Hosmane, R.S. J. Cryst Spectosc. Res. 1987, 17, 533.
Allen, F.H.; Kennard, O.; Watson, D.G.; Brammer, L.; Orpen, A.G. J. Chem. Soc. Perkin Trans. II 1987, S1.
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Banerjee, T., Chaudhuri, S., Moore, M. et al. Synthesis and crystal structures of 5-amino-1-(2-hydroxyethyl)imidazole-4-carboxamide and 5-amino-1-(2-chloroethyl)-4-cyanoimidazole. Journal of Chemical Crystallography 29, 1281–1286 (1999). https://doi.org/10.1023/A:1009561108403
Issue Date:
DOI: https://doi.org/10.1023/A:1009561108403