4-Benzhydryl-1-cinnamylpiperazin-1-ium nitrate

Zong-Ling Ru; Guo-Xi Wang

doi:10.1107/S1600536808019958

. 2008 Jul 12;64(Pt 8):o1463. doi: 10.1107/S1600536808019958

4-Benzhydryl-1-cinnamylpiperazin-1-ium nitrate

Zong-Ling Ru ^a, Guo-Xi Wang ^a,^*

PMCID: PMC2962093 PMID: 21203177

Abstract

In the title compound, C₂₆H₂₉N₂ ⁺·NO₃ ⁻, the dihedral angle formed by the phenyl rings of the benzhydryl group is 66.18 (9)°. Crystal cohesion is enforced by cation–anion C—H⋯O and N—H⋯O hydrogen bonds.

Related literature

For the use of amine derivatives in coordination chemisty, see: Manzur et al. (2007 ▶); Ismayilov et al. (2007 ▶); Austria et al. (2007 ▶).

Experimental

Crystal data

C₂₆H₂₉N₂ ⁺·NO₃ ⁻
M _r = 431.52
Monoclinic,
a = 18.6368 (17) Å
b = 10.8990 (10) Å
c = 12.0271 (10) Å
β = 107.397 (2)°
V = 2331.2 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 293 (2) K
0.27 × 0.18 × 0.15 mm

Data collection

Rigaku Mercury2 diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ▶) T _min = 0.978, T _max = 0.985
22444 measured reflections
5328 independent reflections
2413 reflections with I > 2σ(I)
R _int = 0.100

Refinement

R[F ² > 2σ(F ²)] = 0.071
wR(F ²) = 0.178
S = 1.03
5328 reflections
289 parameters
H-atom parameters constrained
Δρ_max = 0.15 e Å⁻³
Δρ_min = −0.17 e Å⁻³

Data collection: CrystalClear (Rigaku, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL/PC (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL/PC.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808019958/rz2224sup1.cif

e-64-o1463-sup1.cif^{(22.7KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808019958/rz2224Isup2.hkl

e-64-o1463-Isup2.hkl^{(260.9KB, hkl)}

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2N⋯O3	0.90	2.02	2.862 (3)	156
N2—H2N⋯O1	0.90	2.31	3.101 (3)	146
C14—H14A⋯O3	0.97	2.53	3.263 (3)	132
C19—H19⋯O1	0.93	2.29	3.050 (4)	138

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supplementary crystallographic information

Comment

In the past five years, we have focused on the chemistry of amine derivatives because of their multiple coordination modes as ligands to metal ions and for the construction of novel metal–organic frameworks (Manzur et al. 2007; Ismayilov et al. 2007; Austria et al. 2007). We report here the crystal structure of the title compound, 4-benzhydryl-1-cinnamylpiperazin-1-ium nitrate.

In the title compound (Fig. 1), the piperazine ring is protonated at the N2 atom and adopts the usual chair conformation. The phenyl rings of the benzhydryl group form a dihedral angle of 66.18 (9)°. The crystal packing is stabilized by C—H···O and N—H···O hydrogen bonds occurring between adjacent anions and cations (Table 1, Fig. 2).

Experimental

4-Benzhydryl-1-cinnamylpiperazin-1-ium nitrate (3 mmol) was dissolved in ethanol (20 ml). The solvent was slowly evaporated in air affording colourless block-shaped crystals of the title compound suitable for X-ray analysis.