Abstract
2-(4-Chlorophenyl)-3-(phenylamino)-5-(thiophen-2-ylmethylidene)-3,5-dihydro-4H-imidazol-4-one, C20H14N3OSCl was synthesized and its crystal structure was determined by single crystal X-ray diffraction. The crystals are triclinic, sp. gr. P1, Z = 2. All three rings are planar, and imidazole ring is almost perpendicular to the phenyl ring with the dihedral angle of 88.65(2)°. In the crystal, pairs of O–H···O hydrogen bonds link molecules into inversion dimers, featuring R22(10) graph set motif. Crystal structure is further stabilized by π···π interactions.
Similar content being viewed by others
References
T. Nakamura, H. Kakinuma, H. Umemiya, et al. Bioorg. Med. Chem. Lett. 14, 333 (2004).
M. Su Han and D. H. Kim, Bioorg. Med. Chem. Lett. 11, 1425 (2001).
C. Congiu, M. T. Cocco, and V. Onnis, Bioorg. Med. Chem. Lett., 18, 989 (2008).
A. M. Venkatesan, A. Agarwal, T. Abe, et al., Bioorg. Med. Chem., 16, 1890 (2008).
T. Nakamura, H. Kakinuma, H. Umemiya, et al., Bioorg. Med. Chem. Lett., 14, 333 (2004).
G. Roman, J. G. Riley, J. Z. Vlahakis, et al., Bioorg. Med. Chem., 15, 3225 (2007).
P. G. Nanterment, J. C. Barrow, S. R. Lindsley, et al., Bioorg. Med. Chem. Lett., 14, 2141 (2004).
J. L. Adams, J. C. Boehm, T. F. Gallagher, et al., Bioorg. Med. Chem. Lett., 11, 2867 (2001).
K. Shalini, P. K. Sharma, and N. Jumar, Chem. Sin., 1, 36 (2010).
S. Yoshida and H. Ishida, J. Chem. Phys., 78, 6960 (1983).
S. Yoshida and H. Ishida, J. Adhesion 16, 217 (1984).
G. Challa, J. Reedijk, and P. W. N. M. van Leeuwen, Polym. Adv. Technol., 7, 625 (1996).
C. G. Overberger and R. Tomko, ACS Symp. Ser. 212, 13 (1983).
M. Suzuki, S. Kobayashi, T. Koyama, et al., J. Chem. Soc. Faraday Trans. 91, 2877 (1995).
G. Manecke and R. Schlegel, Chem. Macromol. 179, 19 (1978).
J. Wang and C. Chen, Biotechnol. Adv. 27, 195 (2009).
S. Pramanik, S. Dhara, S. S. Bhattacharyya, and P. Chattopadhyay, Anal. Chim. Acta, 556, 430 (2006).
B. L. Rivas, M. Jara, and E. D. Pereira, J. Appl. Polym. Sci. 89 (2003).
M. D. Green and T. E. Long, Rev. Polymer 49, 291 (2009).
R. Suthakaran, S. Kavimani, P. Venkaiaiah, and K. Suganthi, Rasayan J. Chem. 1, 22 (2008).
A. Patel, S. Bari, G. Talele, J. Patel, and M. Sarangapani, Iran. J. Pharm. Res. 4, 249 (2006).
K. Patel, E. Jayachandran, Ravishah, et al. Int. J. Pharm. Bio. Sci. 1, 1 (2010).
M. S. Mohamed, R. K. Mahmoud, A. I. Sayad, and M. E. El-Araby, J. Med. Chem. 2, 24 (2012).
G. E. Suhasini, M. Nirmala, Varalakshmi, et al., Int. J. Pharm. 4, 241 (2014).
G. M. Sheldrick, Acta Crystallogr. A 64, 112 (2008).
L. J. Farrugia, J. Appl. Crystallogr. 32, 837 (1999).
M. Nardelli, J. Appl. Crystallogr. 28, 659 (1995).
A. L. Spek, Acta Crystallogr. D 65, 148 (2009).
L. J. Farrugia, J Appl Crystallogr. 30, 565 (2012).
F. H. Allen, O. Kennard, D. G. Watson, et al., J. Chem. Soc. Perkin Trans-II 1 (1987).
J. Bernstein, R. E. Davis, L. Shimoni, and N. L. Chang, Angew Chem. Int. Ed. Eng. 34, 1555 (1995).
Author information
Authors and Affiliations
Corresponding author
Additional information
The article is published in the original.
Rights and permissions
About this article
Cite this article
Sharma, D.K., Subbulakshmi, K.N., Narayana, B. et al. Synthesis and Molecular Structure of 2-(4-Chlorophenyl)-3-(phenyl-amino)-5-(thiophen-2-ylmethylidene)-3,5-dihydro-4H-imidazol-4-one. Crystallogr. Rep. 62, 1148–1151 (2017). https://doi.org/10.1134/S1063774517070082
Received:
Published:
Issue Date:
DOI: https://doi.org/10.1134/S1063774517070082