Research Article: 1-(2-Nitro­benz­yl)-1H-pyrrole-2-carbaldehyde

Date Published: June 01, 2011

Publisher: International Union of Crystallography

Author(s): Xu Chen, Ying Liu, Deng-Ke Liu, Ping-Bao Wang.


In the title compound, C12H10N2O3, the five- and six-membered rings form a dihedral angle of 83.96 (6)°. The nitro group is twisted by 5.92 (8)° from the plane of the attached benzene ring. In the crystal, weak inter­molecular C—H⋯O hydrogen bonds link the mol­ecules into columns in the [100] direction, with a short distance of 3.725 (3) Å between the centroids of benzene rings inside these columns.

Partial Text

The title compound is an inter­mediate in the synthesis of lixivaptan (systematic name N-[3-chloro-4-(5H-pyrrolo-[2,1-c][1,4]benzodiazepin-10(11H)-ylcarbon­yl)phen­yl]-5-fluoro-2-methyl­benzamide), a vasopressin receptor antagonist with high V2 receptor affinity. For preliminary studies of lixivaptan, which is now undergoing Phase III clinical trials, see, for example, Ku et al. (2009 ▶). For the synthesis of the title compound, see: Albright et al. (1998 ▶).




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