3-Benzyl-6-benzylamino-1-methyl-5- nitro-1,2,3,4-tetrahydropyrimidine M. Kannan, a P. Manivel, a M. Sarathbabu, b R. Sathishkumar, c H. Surya Prakash Rao b and R. Krishna a * a Centre for Bioinformatics, Pondicherry University, Puducherry 605 014, India, b Department of Chemistry, Pondicherry University, Puducherry 605 014, India, and c Solid State and Structural Chemistry Unit, Indian Institute of Science, Bangalore 560 012, India Correspondence e-mail: krishstrucbio@gmail.com Received 18 January 2010; accepted 28 January 2010 Key indicators: single-crystal X-ray study; T = 292 K; mean (C–C) = 0.004 A ˚ ; R factor = 0.067; wR factor = 0.160; data-to-parameter ratio = 17.5. In the title compound, C 19 H 22 N 4 O 2 , the tetrahydropyrimidine ring adopts an envelope conformation (with the N atom connected to the benzyl group representing the flap). This benzyl group occupies a quasi-axial position. The two benzyl groups lie over the tetrahydropyridimidine ring. The amino group is a hydrogen-bond donor to the nitro group. Related literature For the biological activity of tetrahydropyrimidine derivatives, see: Atwal et al. (1991); Jauk et al. (2000); Messer et al. (1997). For the synthesis of the title compound, see: Chanda et al. (2004). For conformational anlysis, see: Cremer & Pople (1975). Experimental Crystal data C 19 H 22 N 4 O 2 M r = 338.41 Trigonal, R 3 a = 29.2634 (12) A ˚ c = 10.4916 (8) A ˚ V = 7780.8 (7) A ˚ 3 Z = 18 Mo Kradiation = 0.09 mm 1 T = 292 K 0.28 0.23 0.19 mm Data collection Oxford Diffraction Xcalibur diffractometer with an Eos (Nova) detector Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009) T min = 0.979, T max = 0.983 28183 measured reflections 3973 independent reflections 2683 reflections with I >2(I) R int = 0.044 Standard reflections: 0 Refinement R[F 2 >2(F 2 )] = 0.067 wR(F 2 ) = 0.160 S = 1.08 3973 reflections 227 parameters H-atom parameters constrained Á max = 0.27 e A ˚ 3 Á min = 0.24 e A ˚ 3 Table 1 Hydrogen-bond geometry (A ˚ , ). D—HA D—H HA DA D—HA N3—H3O2 0.86 1.98 2.591 (2) 127 Data collection: CrysAlis PRO (Oxford Diffraction, 2009); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); soft- ware used to prepare material for publication: PLATON (Spek, 2009). The authors acknowledge Centre of Excellence in Bioin- formatics, Pondicherry University, for providing the facilities to carry out this work. Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: NG2723). References Atwal, K. S., Swanson, B. N., Unger, S. E., Floyd, D. M., Moreland, S., Hedberg, A. & O Reilly, B. C. (1991). J. Med. Chem. 34, 806–811. Chanda, K., Dutta, M. C., Kishore, K. & Vishwakarma, J. N. (2004). Molbank 2004,M367. Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354–1358. Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. Jauk, B., Pernat, T. & Kappe, C. O. (2000). Molecules. 5, 227–239. Messer, W. S., Abuh, Y. F., Liu, Y., Periyasamy, S., Ngur, D. O., Edgar, M. A. N., ElAssadi, A. A., Sbeih, S., Dunbar, P. G., Roknich, S., Rho, T., Fang, Z., Ojo, B., Zhang, H., Huzl, J. J. & Nagy, P. I. (1997). J. Med. Chem. 40, 1230–1246. Oxford Diffraction (2009). CrysAlis CCD and CrysAlis PRO RED. Oxford Diffraction Ltd, Yarnton, England. Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Spek, A. L. (2009). Acta Cryst. D65, 148–155. organic compounds Acta Cryst. (2010). E66, o515 doi:10.1107/S160053681000348X Kannan et al. o515 Acta Crystallographica Section E Structure Reports Online ISSN 1600-5368