Received 19 March 2013
In the title compound, C21H11N5S, the phenothiazine unit has a butterfly structure, and the central six-membered ring adopts a boat conformation. The dihedral angle between the benzene rings is 127.64 (6)°, which is smaller than those reported for similar compounds because of the steric repulsion between the phenothiazine and its tetracyano-1,3-butadiene substituent. The dicyanovinyl groups are almost orthogonal to one another, making a dihedral angle of 80.58 (6)°. In the crystal, the molecules are aligned along the b axis. Four kinds of weak C-HN interactions are recognized, one of which connects the molecules into a one-dimensional array and the remaining three link these arrays.
For applications of tetracyano-1,3-butadienes in photonics and non-linear optics, see: Faupel et al. (2007). For the preparation and structure of 10-(prop-1-yn-1-yl)-10H-phenothiazine, see: Zaugg et al. (1958); Umezono & Okuno (2012). For the structures of other related N-substituted phenothiazines, see: Chu & Van der Helm (1974, 1975); Tokunaga & Okuno (2012).
Data collection: CrystalClear (Rigaku, 2008); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: CrystalStructure (Rigaku, 2010).
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SJ5308 ).
This work was supported by Research for Promoting Technological Seeds from the Japan Science and Technology Agency (JST).
Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M. C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435.
Chu, S. S. C. & Van der Helm, D. (1974). Acta Cryst. B30, 2489-2490.
Chu, S. S. C. & Van der Helm, D. (1975). Acta Cryst. B31, 1179-1183.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.
Faupel, F., Dimitrakopoulos, C., Kahn, A. & Wöll, C. (2007). Chem. Rev. 107, 923-1386.
Flack, H. D. (1983). Acta Cryst. A39, 876-881.
Rigaku (2008). CrystalClear. Rigaku Corporation, Tokyo, Japan.
Rigaku (2010). CrystalStructure. Rigaku Corporation, Tokyo, Japan.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Tokunaga, E. & Okuno, T. (2012). Acta Cryst. E68, o3369.
Umezono, S. & Okuno, T. (2012). Acta Cryst. E68, o2790.
Zaugg, H. E., Sweett, L. R. & Stone, G. R. (1958). J. Org. Chem. 23, 1389-1390.