3-Amino-1-(thiophen-2-yl)-9,10-dihydrophenanthrene-2,4-dicarbonitrile

Abdulrahman O Al-Youbi,Seik Weng Ng,Hassan M Faidallah,Edward R T Tiekink,Abdullah M Asiri

doi:10.1107/s1600536812010033

Abdulrahman O Al-Youbi, Seik Weng Ng + Show 3 more

Open Access

https://doi.org/10.1107/s1600536812010033

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Abstract

In the title compound, C20H13N3S, the partially saturated ring adopts a twisted half-boat conformation with the methylene C atom closest to the aminobenzene ring lying 0.690 (6) Å out of the plane defined by the five remaining atoms. The dihydrophenanthrene residue has a folded conformation [dihedral angle between the outer benzene rings = 26.27 (18)°]. The thiophen-2-yl ring forms a dihedral angle of 63.76 (19)° with the benzene ring to which it is attached. In the crystal, inversion dimers linked by pairs of N—H⋯N hydrogen bonds generate R 2 2(12) loops. The dimers are linked into layers in the bc plane by weak C—H⋯π interactions. The thiophen-2-yl ring is disordered over two essentially coplanar but opposite orientations in a 0.918 (4):0.082 (4) ratio.

Highlights

Atom closest to the aminobenzene ring lying 0.690 (6) Å out of the plane defined by the five remaining atoms
Inversion dimers linked by pairs of N—H N hydrogen bonds generate R22(12) loops
The authors are grateful to the Center of Excellence for Advanced Materials Research and the Chemistry Department at King Abdulaziz University for providing the research facilities

Summary

Agilent SuperNova Dual diffractometer with an Atlas detector

Tmin = 0.940, Tmax = 0.994 a Chemistry Department, Faculty of Science, King Abdulaziz University, PO Box. Key indicators: single-crystal X-ray study; T = 100 K; mean (C–C) = 0.005 Å; disorder in main residue; R factor = 0.066; wR factor = 0.164; data-to-parameter ratio = 11.9. The dihydrophenanthrene residue has a folded conformation [dihedral angle between the outer benzene rings = 26.27 (18) ]. The thiophen-2-yl ring forms a dihedral angle of 63.76 (19) with the benzene ring to which it is attached. Inversion dimers linked by pairs of N—H N hydrogen bonds generate R22(12) loops. The dimers are linked into layers in the bc plane by weak C—H interactions. The thiophen-2-yl ring is disordered over two essentially coplanar but opposite orientations in a 0.918 (4):0.082 (4) ratio

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