1-Piperonylpiperazinium picrate
IN THE CATION OF THE TITLE SALT [SYSTEMATIC NAME: 4-(2H-1,3-benzodioxol-5-ylmeth-yl)piperazin-1-ium 2,4,6-tri-nitro-phen-o-late], C12H17N2O2 (+)·C6H2N3O7 (-), the piperazine ring adopts a slightly disordered chair conformation. The piperonyl ring system and the piperazine ring are twisted with respe...
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| Published in | Acta crystallographica. Section E, Structure reports online Vol. 70; no. Pt 2; pp. o208 - o209 |
|---|---|
| Main Authors | , , , , |
| Format | Journal Article |
| Language | English |
| Published |
United States
International Union of Crystallography
01.02.2014
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| Subjects | |
| Online Access | Get full text |
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| Abstract | IN THE CATION OF THE TITLE SALT [SYSTEMATIC NAME: 4-(2H-1,3-benzodioxol-5-ylmeth-yl)piperazin-1-ium 2,4,6-tri-nitro-phen-o-late], C12H17N2O2 (+)·C6H2N3O7 (-), the piperazine ring adopts a slightly disordered chair conformation. The piperonyl ring system and the piperazine ring are twisted with respect to each other with an N-C-C-C torsion angle of 40.7 (2)°. In the anion, the dihedral angles between the mean planes of the nitro substituents ortho to the phenolate O atom and the mean plane of the phenyl ring are 28.8 (9) and 32.2 (8)°. In contrast, the nitro group in the para position lies much closer to the aromatic ring plane, subtending a dihedral angle of 3.0 (1)°. In the crystal, the cations and anions inter-act through N-H⋯O hydrogen bonds and a weak C-H⋯O inter-action. Weak C-H⋯O inter-actions are also observed between the anions, forming R 2 (2)(10) graph-set ring motifs. In addition, a weak centroid-centroid π-π stacking inter-action between the aromatic rings of the cation and the anion, with an inter-centroid distance of 3.7471 (9) Å, contributes to the crystal packing, resulting in a two-dimensional network along (10-1). |
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| AbstractList | In the cation of the title salt [systematic name: 4-(2
H
-1,3-benzodioxol-5-ylmethyl)piperazin-1-ium 2,4,6-trinitrophenolate], C
12
H
17
N
2
O
2
+
·C
6
H
2
N
3
O
7
−
, the piperazine ring adopts a slightly disordered chair conformation. The piperonyl ring system and the piperazine ring are twisted with respect to each other with an N—C—C—C torsion angle of 40.7 (2)°. In the anion, the dihedral angles between the mean planes of the nitro substituents
ortho
to the phenolate O atom and the mean plane of the phenyl ring are 28.8 (9) and 32.2 (8)°. In contrast, the nitro group in the
para
position lies much closer to the aromatic ring plane, subtending a dihedral angle of 3.0 (1)°. In the crystal, the cations and anions interact through N—H⋯O hydrogen bonds and a weak C—H⋯O interaction. Weak C—H⋯O interactions are also observed between the anions, forming
R
2
2
(10) graph-set ring motifs. In addition, a weak centroid–centroid π–π stacking interaction between the aromatic rings of the cation and the anion, with an intercentroid distance of 3.7471 (9) Å, contributes to the crystal packing, resulting in a two-dimensional network along (10-1). IN THE CATION OF THE TITLE SALT [SYSTEMATIC NAME: 4-(2H-1,3-benzodioxol-5-ylmeth-yl)piperazin-1-ium 2,4,6-tri-nitro-phen-o-late], C12H17N2O2 (+)·C6H2N3O7 (-), the piperazine ring adopts a slightly disordered chair conformation. The piperonyl ring system and the piperazine ring are twisted with respect to each other with an N-C-C-C torsion angle of 40.7 (2)°. In the anion, the dihedral angles between the mean planes of the nitro substituents ortho to the phenolate O atom and the mean plane of the phenyl ring are 28.8 (9) and 32.2 (8)°. In contrast, the nitro group in the para position lies much closer to the aromatic ring plane, subtending a dihedral angle of 3.0 (1)°. In the crystal, the cations and anions inter-act through N-H⋯O hydrogen bonds and a weak C-H⋯O inter-action. Weak C-H⋯O inter-actions are also observed between the anions, forming R 2 (2)(10) graph-set ring motifs. In addition, a weak centroid-centroid π-π stacking inter-action between the aromatic rings of the cation and the anion, with an inter-centroid distance of 3.7471 (9) Å, contributes to the crystal packing, resulting in a two-dimensional network along (10-1). In the cation of the title salt [systematic name: 4-(2 H -1,3-benzodioxol-5-ylmethyl)piperazin-1-ium 2,4,6-trinitrophenolate], C 12 H 17 N 2 O 2 + ·C 6 H 2 N 3 O 7 − , the piperazine ring adopts a slightly disordered chair conformation. The piperonyl ring system and the piperazine ring are twisted with respect to each other with an N—C—C—C torsion angle of 40.7 (2)°. In the anion, the dihedral angles between the mean planes of the nitro substituents ortho to the phenolate O atom and the mean plane of the phenyl ring are 28.8 (9) and 32.2 (8)°. In contrast, the nitro group in the para position lies much closer to the aromatic ring plane, subtending a dihedral angle of 3.0 (1)°. In the crystal, the cations and anions interact through N—H...O hydrogen bonds and a weak C—H...O interaction. Weak C—H...O interactions are also observed between the anions, forming R 2 2 (10) graph-set ring motifs. In addition, a weak centroid–centroid π–π stacking interaction between the aromatic rings of the cation and the anion, with an intercentroid distance of 3.7471 (9) Å, contributes to the crystal packing, resulting in a two-dimensional network along (10-1). In the cation of the title salt [systematic name: 4-(2H-1,3-benzodioxol-5-ylmethyl)piperazin-1-ium 2,4,6-trinitrophenolate], C12H17N2O2+·C6H2N3O7−, the piperazine ring adopts a slightly disordered chair conformation. The piperonyl ring system and the piperazine ring are twisted with respect to each other with an N—C—C—C torsion angle of 40.7 (2)°. In the anion, the dihedral angles between the mean planes of the nitro substituents ortho to the phenolate O atom and the mean plane of the phenyl ring are 28.8 (9) and 32.2 (8)°. In contrast, the nitro group in the para position lies much closer to the aromatic ring plane, subtending a dihedral angle of 3.0 (1)°. In the crystal, the cations and anions interact through N—H...O hydrogen bonds and a weak C—H...O interaction. Weak C—H...O interactions are also observed between the anions, forming R22(10) graph-set ring motifs. In addition, a weak centroid–centroid π–π stacking interaction between the aromatic rings of the cation and the anion, with an intercentroid distance of 3.7471 (9) Å, contributes to the crystal packing, resulting in a two-dimensional network along (10-1). |
| Author | Yathirajan, H S Jasinski, Jerry P Anderson, Brian J Kavitha, Channappa N Kaur, Manpreet |
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| References | Cremer (sj5385_bb7) 1975; 97 Sheldrick (sj5385_bb13) 2008; 64 Kharb (sj5385_bb10) 2012; 4 Palatinus (sj5385_bb12) 2007; 40 Capuano (sj5385_bb5) 2000; 56 Choudhary (sj5385_bb6) 2006; 14 Brockunier (sj5385_bb4) 2004; 14 Elliott (sj5385_bb9) 2011; 3 Dolomanov (sj5385_bb8) 2009; 42 Millan (sj5385_bb11) 2001; 297 sj5385_bb1 Bogatcheva (sj5385_bb3) 2006; 49 Allen (sj5385_bb2) 1987; 2 |
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| Snippet | IN THE CATION OF THE TITLE SALT [SYSTEMATIC NAME: 4-(2H-1,3-benzodioxol-5-ylmeth-yl)piperazin-1-ium 2,4,6-tri-nitro-phen-o-late], C12H17N2O2 (+)·C6H2N3O7 (-),... In the cation of the title salt [systematic name: 4-(2 H -1,3-benzodioxol-5-ylmethyl)piperazin-1-ium 2,4,6-trinitrophenolate], C 12 H 17 N 2 O 2 + ·C 6 H 2 N 3... In the cation of the title salt [systematic name: 4-(2 H -1,3-benzodioxol-5-ylmethyl)piperazin-1-ium 2,4,6-trinitrophenolate], C 12 H 17 N 2 O 2 + ·C 6 H... In the cation of the title salt [systematic name: 4-(2H-1,3-benzodioxol-5-ylmethyl)piperazin-1-ium 2,4,6-trinitrophenolate], C12H17N2O2+·C6H2N3O7−, the... |
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| Title | 1-Piperonylpiperazinium picrate |
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