7-Chloro-3-(4-methyl-benzene-sulfon-yl)pyrrolo[1,2-c]pyrimidine.

Easha Narayan,Liangfeng Fu,Manpreet Kaur,Gordon W Gribble,Jerry P Jasinski

doi:10.1107/s241431462000382x

Easha Narayan, Liangfeng Fu + Show 3 more

Open Access

https://doi.org/10.1107/s241431462000382x

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Journal: IUCrData	Publication Date: Mar 27, 2020
Citations: 1	License type: CC BY 4.0

Affiliation: Dartmouth College, Keene State College

Abstract

In the title compound, C14H11ClN2O2S, the dihedral angle between the pyrrolo-[1,2-c]pyrimidine ring system (r.m.s. deviation = 0.008 Å) and the benzene ring is 80.2 (9)°. In the crystal, inversion dimers linked by pairs of C-H⋯O inter-actions generate R 2 2(16) loops. Several aromatic π-π stacking inter-actions between the pyrrolo-[1,2-c]pyrimidine rings, as well as separately between the pyrrolo and pyrimidine groups [shortest centroid-centroid separation = 3.5758 (14) Å], help to consolidate the packing.

Highlights

In the title compound, C14H11ClN2O2S, the dihedral angle between the pyrrolo[1,2-c]pyrimidine ring system (r.m.s. deviation = 0.008 A ) and the benzene ring is 80.2 (9)
As part of our studies in this area, we report the crystal structure of the title compound, C14H11N2O2SCl (Fig. 1)
We believe that this is the first crystal structure to be reported of a pyrrolo[1,2-c]pyrimidine and one of the few unsymmetrical ‘diaryl sulfones’ to be described

Summary

Structure description

Pyrrolo[1,2-c]pyrimidines are a class of fused heterocycles of interest for their biological activity, electrochemical properties, and as components of natural products (Tatu et al, 2018). The C1—S1—C8 bond angle of 105.03 (10) is consistent with the literature data (Sime & Woodhouse, 1974; Bocelli & Rizzoli, 1990; Colquhoun et al, 2002). A weak C14—H14BÁ Á ÁO2 hydrogen bond (Table 1) links two molecules together in a ring face–ring face arrangement (Fig. 2). This packing motif was observed by Sime & Woodhouse (1974) in the crystal structure of diphenyl sulfone and by Colquhoun et al (2002) in the crystal structure of poly(1,4-phenylenesulfone). Several aromatic – stacking interactions between the pyrrolo[1,2-c]pyrimidine rings as well as separately between the pyrrolo and pyrimidine groups (Table 2) are observed and help to consolidate the packing

Synthesis and crystallization

HÁ Á ÁA

No of parameters

Crystal data

Data collection

Findings

Special details