4,4′-[Piperazine-1,4-diylbis(propyl­ene­nitrilo­methyl­idyne)]diphenol

Ruibo Xu; Xingyou Xu; Xujie Yang; Yuping Huang; Chunmei Xu

doi:10.1107/S1600536809045620

. 2009 Nov 4;65(Pt 12):o2996. doi: 10.1107/S1600536809045620

4,4′-[Piperazine-1,4-diylbis(propylenenitrilomethylidyne)]diphenol

Ruibo Xu ^a, Xingyou Xu ^b,^*, Xujie Yang ^c, Yuping Huang ^a, Chunmei Xu ^a

PMCID: PMC2972058 PMID: 21578736

Abstract

In the title molecule, C₂₄H₃₂N₄O₂, the piperazine ring adopts a chair conformation and the dihedral angle between the two benzene rings is 35.4 (1)°. In the crystal structure, intermolecular O—H⋯N hydrogen bonds link molecules into chains along [001].

Related literature

For the properties of piperazine derivatives, see: Keypour et al. (2008 ▶, 2009 ▶); Paital et al. (2009 ▶). For related structures, see: Thirumurugan et al. (1998 ▶); Yogavel et al. (2003 ▶). graphic file with name e-65-o2996-scheme1.jpg

Experimental

Crystal data

C₂₄H₃₂N₄O₂
M _r = 408.54
Monoclinic,
a = 5.9701 (10) Å
b = 30.159 (3) Å
c = 12.8348 (18) Å
β = 97.558 (2)°
V = 2290.9 (6) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 298 K
0.17 × 0.15 × 0.11 mm

Data collection

Siemens SMART CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.987, T _max = 0.992
5997 measured reflections
2016 independent reflections
1387 reflections with I > 2σ(I)
R _int = 0.068

Refinement

R[F ² > 2σ(F ²)] = 0.043
wR(F ²) = 0.103
S = 0.96
2016 reflections
271 parameters
2 restraints
H-atom parameters constrained
Δρ_max = 0.14 e Å⁻³
Δρ_min = −0.19 e Å⁻³

Data collection: SMART (Siemens, 1996 ▶); cell refinement: SAINT (Siemens, 1996 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809045620/lh2937sup1.cif

e-65-o2996-sup1.cif^{(22.5KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809045620/lh2937Isup2.hkl

e-65-o2996-Isup2.hkl^{(99.2KB, 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
O2—H2⋯N1ⁱ	0.82	1.98	2.762 (4)	159
O1—H1⋯N2ⁱⁱ	0.82	2.00	2.780 (4)	159

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Symmetry codes: (i) Inline graphic ; (ii) .

Acknowledgments

This project was supported by the Key Project for Fundamental Research of the Jiangsu Provincial Educational Committee (07KJA150011), the Opened Funds of Jiangsu Key Laboratory of Marine Biotechnology of Huaihai Institute of Technology (2009HS06) and the QingLan Project of Jiangsu Province (2008).

supplementary crystallographic information

Comment

Piperazine derivatives possesses interesting structures and properties (Yogavel et al., 2003; Thirumurugan et al., 1998; Keypour et al., 2008,2009; Paital et al., 2009), therefore, our group have designed and prepared series of Schiff bases and complexes derived from substituted piperazines. As part of our work, the title compound (I) a potential hexadentate Schiff base ligand, was synthesized in our group and herein we report the crystal structure.

The molecular structure of (I) is shown in Fig. 1. In (I), the C8—N3 and C18—N4 double bond lengths are comparable to reported values (Yogavel et al., 2003; Thirumurugan et al., 1998). The dihedral angle between the two benzene rings (C9—C14 and C19—C24) is 35.4 (1) °. In the piperazine ring, atoms C1/C2/C3/C4 are essentially planar (the mean deviation from the plane is 0.0032 Å), and atoms N1 and N2 atom lie 0.6936 and 0.6693 Å either side of this plane. This four atom plane makes a dihedral angle of 50.9 (3)° with the plane of atoms C2/N2/C3 and 52.7 (3) ° with atoms C1/N1/C4, respectively, in accordance with the chair conformation of the piperazine ring. In the crystal structure, intermolecular O—H···N hydrogen bonds link molecules into one-dimensional chains along [001](Fig.2).

Experimental

A solution of N,N'-bis(N-aminopropyl)-piperazine (1.5 mmol in 10 ml anhydrous methanol) was added dropwise with constant stirring to a solution of parahydroxybenzaldehyde (3 mmol in 15 ml anhydrous methanol) at 325 K for 3 h. The resulting mixture was filtered. After cooling, the filtrate was evaporated at ambient environment. Several days later, pink crystals suitable for X-ray analysis were collected and washed with small amount of methanol and dried at room temperature.