Synthesis and crystal structure of anti-10-butyl-10,11,22,23-tetra-hydro-9 H,21 H-5,8:15,12-bis(metheno)[1,5,11]tri-aza-cyclo-hexa-decino[1,16- a:5,6- a']di-indole

Koji Kubono; Keita Tani; Yukiyasu Kashiwagi; Fumito Tani; Taisuke Matsumoto

doi:10.1107/S2056989022003383

Synthesis and crystal structure of anti-10-butyl-10,11,22,23-tetra-hydro-9 H,21 H-5,8:15,12-bis(metheno)[1,5,11]tri-aza-cyclo-hexa-decino[1,16- a:5,6- a']di-indole

Acta Crystallogr E Crystallogr Commun. 2022 Apr 5;78(Pt 5):477-480. doi: 10.1107/S2056989022003383. eCollection 2022 May 1.

Authors

Koji Kubono¹, Keita Tani¹, Yukiyasu Kashiwagi², Fumito Tani³, Taisuke Matsumoto⁴

Affiliations

¹ Osaka Kyoiku University, 4-698-1 Asahigaoka, Kashiwara, Osaka 582-8582, Japan.
² Osaka Research Institute of Industrial Science and Technology, 1-6-50 Morinomiya, Joto-ku, Osaka 536-8553, Japan.
³ Institute for Materials Chemistry and Engineering, Kyushu University, 744 Motooka, Nishi-ku, Fukuoka 819-0395, Japan.
⁴ Institute for Materials Chemistry and Engineering, Kyushu University, 6-1 Kasuga koen, Kasuga, Fukuoka 816-8580, Japan.

Abstract

The title compound, C₃₃H₃₃N₃, is a carbazolophane, which is a cyclo-phane composed of two carbazole fragments. It has a planar chirality but crystallizes as a racemate in the space group P . The mol-ecule adopts an anti-configuration, in which two carbazole fragments are partially overlapped. Both carbazole ring systems are slightly bent, with the C atoms at 3-positions showing the largest deviations from the mean planes. The dihedral angle between two carbazole fragments is 5.19 (3)°, allowing an intra-molecular slipped π-π inter-action [Cg⋯Cg = 3.2514 (8) Å]. In the crystal, the mol-ecules are linked via inter-molecular C-H⋯N hydrogen bonds and C-H⋯π inter-actions into a network sheet parallel to the ab plane. The mol-ecules of different sheets form other C-H⋯π inter-actions, thus forming a three-dimensional network.

Keywords: C—H⋯N hydrogen bonds; C—H⋯π interactions; carbazolophane; crystal structure; racemate.

Grants and funding

Funding for this research was provided by: the Japan Science and Technology Agency’s Core Research for Evolutional Science and Technology (grant No. JPMJCR2001); Network Joint Research Center for Materials and Devices (grant No. 20211332); JSPS KAKENHI (grant No. JP20K05565).