(Anthracen-9-ylmeth­yl)benzyl­ammonium chloride

Jian-Rong Han; Wei Wang; Xiao-Li Zhen; Xia Tian; Shou-Xin Liu

doi:10.1107/S1600536811016837

. 2011 May 20;67(Pt 6):o1482. doi: 10.1107/S1600536811016837

(Anthracen-9-ylmethyl)benzylammonium chloride

Jian-Rong Han ^a,^*, Wei Wang ^a, Xiao-Li Zhen ^a, Xia Tian ^a, Shou-Xin Liu ^b,^‡

PMCID: PMC3120425 PMID: 21754851

Abstract

In the title compound, C₂₂H₂₀N⁺·Cl⁻, the anthracene system makes a dihedral angle of 72.65 (4)° with the benzene ring. The C—N—C—C torsion angles in the chain connecting the benzene ring and anthracene system are 52.24 (15) and −170.73 (11)°. The crystal structure is stabilized by intermolecular N—H⋯Cl and C—H⋯Cl hydrogen bonds, which link the molecules into tetramers about inversion centers.

Related literature

For the synthesis and structures of related compounds, see: Ashton et al. (1997 ▶). For formation of rotaxanes from sec-ammonium salts and crown ethers, see: Nakazono et al. (2008 ▶).

Experimental

Crystal data

C₂₂H₂₀N⁺·Cl⁻
M _r = 333.84
Triclinic,
a = 6.7457 (13) Å
b = 10.761 (2) Å
c = 13.033 (3) Å
α = 94.45 (3)°
β = 104.84 (3)°
γ = 104.48 (3)°
V = 875.3 (3) Å³
Z = 2
Mo Kα radiation
μ = 0.22 mm⁻¹
T = 113 K
0.28 × 0.24 × 0.20 mm

Data collection

Rigaku Saturn CCD area-detector diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005 ▶) T _min = 0.941, T _max = 0.957
5882 measured reflections
3048 independent reflections
2342 reflections with I > 2σ(I)
R _int = 0.027

Refinement

R[F ² > 2σ(F ²)] = 0.031
wR(F ²) = 0.088
S = 1.04
3048 reflections
226 parameters
3 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.21 e Å⁻³

Data collection: CrystalClear (Rigaku/MSC, 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 (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811016837/pv2409sup1.cif

e-67-o1482-sup1.cif^{(20.2KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811016837/pv2409Isup2.hkl

e-67-o1482-Isup2.hkl^{(149.5KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811016837/pv2409Isup3.cml

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
N1—H1A⋯Cl1ⁱ	0.92 (1)	2.26 (1)	3.0963 (13)	152 (1)
N1—H1B⋯Cl1	0.92 (1)	2.17 (1)	3.0781 (16)	170 (1)
C16—H16A⋯Cl1ⁱⁱ	0.97	2.60	3.4824 (16)	151

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

Acknowledgments

We are grateful for financial support from the Hebei Natural Science Fundation (No. B2009000670) and the Foundation of the Education Department of Hebei Province (grant No. 2009117), People’s Republic of China.

supplementary crystallographic information

Comment

Sec-ammonium salts and crown ethers combine well to yield a stable pseudorotaxanes as a precursor of rotaxanes (Nakazono et al., 2008). (9-Anthracenyl) benzylammonium hexafluorophosphate and aromatic crown ethers give hydrogen-bonded complexes pseudorotaxane-like geometries (Ashton et al., 1997). In this paper we report the synthesis and crystal strucure of (9-anthracenyl) benzyl ammonium chloride.

In the title compound (Fig. 1), anthracene ring makes a dihedral angle of 72.65 (4)° with benzene ring. The torsion angles in the chain connecting the benzene and the anthracene rings, (C15/N1—C16/C17 and (C16/N1—C15/C14) are 52.24 (15) ° and -170.73 (11)°, respectively. In the crystal structure, the crystal packing is stabilized by intermolecular N1—H1A···Cl1 and C16—H16A···Cl1 hydrogen bonds which link the molecules into tetramers about inversion centers (Table 1 and Fig. 2).

Experimental

A mixture of 9-anthracenealdehyde (6.18 g, 30 mmol) and benzylamine (3.86 g, 36 mmol) and molecular Sieve in toluene (200 mL) was heated under reflux with stirring in a water divider for 10 h. After the reaction mixture had cooled down to room temperature, the solvent was removed in vacuo to give the imine. The solid was dissolved in hot MeOH (150 mL), followed by drop-wise addition of NaBH₄ (5.70 g, 150 mmol) and heating under reflux with stirring for 8 h. The reaction mixture was then allowed to cool down to room temperature, and concentrated HCl was added (pH<2). After evaporation of the solvent, the residue was suspended in H₂O (70 mL) and extracted with CH₂Cl₂ (4 × 50 mL). The combined extracts were washed with 5% aqueous NaHCO₃ (2× 70 mL) and H₂O (70 mL) and then dried (MgSO₄). Removal of the solvent in vacuo afforded the (9-anthracenyl)benzyl amine which was treated according to literature (Ashton et al., 1997) to prepare the title compound. Pale yellow single crystals of the title compound suitable for X-ray analysis were obtained by slow evaporation of an methnol solution.