4-(2,3-Di-chloro-phen-yl)piperazin-1-ium picrate.

Udhayasuriyan Sathya,Abdul Razak Ibrahim,Shyamaladevi Ramu,Sundaramoorthy Gomathi,Jeyaraman Selvaraj Nirmal Ram,Samson Jegan Jennifer

doi:10.1107/s2414314621003795

Udhayasuriyan Sathya, Abdul Razak Ibrahim + Show 4 more

Open Access

https://doi.org/10.1107/s2414314621003795

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Abstract

The title compound, C6H2N3O7 -·C10H13Cl2N2 +, crystallizes with one 1-(2,3-di-chloro-phen-yl)piperazine (DP) cation and one picrate (PA) anion in the asymmetric unit. In the crystal structure, the DP cation and PA anion are inter-connected via several N-H⋯O and C-H⋯O hydrogen bonds. The DP cation and PA anion are further connected through C-Cl⋯π [3.8201 (4), 3.7785 (4) Å] and N-O⋯π [3.7814 (4) Å] inter-actions. The DP cations are further inter-connected via a weak inter-molecular Cl⋯Cl [3.2613 (4) Å] halogen-halogen inter-action. The combination of these supra-molecular inter-actions leads to a herringbone like supra-molecular architecture.

Highlights

The title compound, C6H2N3O7ÀÁC10H13Cl2N2+, crystallizes with one 1-(2,3dichloro-phenyl)piperazine (DP) cation and one picrate (PA) anion in the asymmetric unit
The DP cation and PA anion are interconnected via several N—HÁ Á ÁO and C—HÁ Á ÁO hydrogen bonds
The DP cation and PA anion are further connected through C—ClÁ Á Á [3.8201 (4), 3.7785 (4) A ] and N—OÁ Á Á [3.7814 (4) A ] interactions

Summary

Structure description

1-(2,3-Dichlorophenyl)piperazine (DP), a precursor in the synthesis of potent drugs such as aripiperazole (AP) (Oshiro et al, 1998), is used as an antipsychotic drug for the treatment of schizophrenia (Braun et al, 2009; Frank et al, 2007). A survey of the Cambridge Structural Database (CSD version 5.40, updates of May 2019; Groom et al, 2016) shows that there are no reports of salt and co-crystal forms of this compound. We report the crystal structure of a new solid form of DP, 1-(2,3-dichloro-phenyl)piperazinium picrate (1). The title salt, 1, crystallizes in the monoclinic P21/n space group. The protonated DP cation interacts with the neighbouring deprotonated PA anions via N1—H1AÁ Á ÁO4i, N1—H1BÁ Á ÁO2ii and N1—H1BÁ Á ÁO7ii hydrogen bonds and C2—. The combination of N1—H1BÁ Á ÁO7, N1—H1BÁ Á ÁO2 and C5—H5AÁ Á ÁO7 interactions between the ions leads to the formation of six-membered rings with graph-set notation R21(6) and R12(6) (Bernstein et al, 1995; Motherwell et al, 2000). Atom H1B of the amino group (N1) acts as a bifurcated

DÁ Á ÁA

Synthesis and crystallization

No of parameters

Crystal data

Data collection

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