Pyrrolidin-1-ium 2-(naphthalen-1-yl)acetate–2-(naphthalen-1-yl)acetic acid (1/1)

Zhao Hong; Fu-Jun Yin; Xing-You Xu; Li-Jun Han; Li Ren

doi:10.1107/S160053681201001X

. 2012 Mar 17;68(Pt 4):o1113. doi: 10.1107/S160053681201001X

Pyrrolidin-1-ium 2-(naphthalen-1-yl)acetate–2-(naphthalen-1-yl)acetic acid (1/1)

Zhao Hong ^a, Fu-Jun Yin ^b,^*, Xing-You Xu ^c, Li-Jun Han ^d, Li Ren ^e

PMCID: PMC3344061 PMID: 22589970

Abstract

In the title compound, C₄H₁₀N⁺·C₁₂H₉O₂ ⁻·C₁₂H₁₀O₂, the pyrrolidine ring adopts an envelope conformation and the dihedral angle between the planes of the two naphthalene ring systems is 8.34 (10)°. The crystal structure is stabilized by O—H⋯O and N—H⋯O hydrogen bonds.

Related literature

For the crystal structures of related naphthalene-1-yl-acetate complexes, see: Yin et al. (2010 ▶); Chen et al. (2004 ▶); Yang et al. (2008 ▶); Tang et al. (2006 ▶); Ji et al. (2011 ▶).

Experimental

Crystal data

C₄H₁₀N⁺·C₁₂H₉O₂ ⁻·C₁₂H₁₀O₂
M _r = 443.52
Monoclinic,
a = 9.4696 (12) Å
b = 19.359 (2) Å
c = 14.3888 (14) Å
β = 115.975 (6)°
V = 2371.3 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 298 K
0.24 × 0.18 × 0.15 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2008) T _min = 0.980, T _max = 0.988
21508 measured reflections
5453 independent reflections
3296 reflections with I > 2σ(I)
R _int = 0.024

Refinement

R[F ² > 2σ(F ²)] = 0.062
wR(F ²) = 0.211
S = 1.05
5453 reflections
298 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.43 e Å⁻³
Δρ_min = −0.22 e Å⁻³

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT (Bruker, 2008 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: DIAMOND (Brandenburg & Berndt, 1999 ▶); software used to prepare material for publication: SHELXL97.

Supplementary Material

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S160053681201001X/wn2468sup1.cif

e-68-o1113-sup1.cif^{(30.6KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681201001X/wn2468Isup2.hkl

e-68-o1113-Isup2.hkl^{(261.6KB, hkl)}

Supplementary material file. DOI: 10.1107/S160053681201001X/wn2468Isup3.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
O1B—H1B⋯O2A	0.82	1.77	2.581 (2)	170
N1C—H1C3⋯O2A	0.90	1.83	2.728 (3)	175
N1C—H1C4⋯O1Aⁱ	0.90	1.83	2.719 (3)	169

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Symmetry code: (i) Inline graphic .

Acknowledgments

The authors thank Jiangsu Marine Resources Development Research Institute and Huaihai Institute of Technology for support of this work.

supplementary crystallographic information

Comment

1-Naphthyl acetate is well known as a ligand capable of forming transition metal complexes (Yin et al., 2011; Liu et al., 2007; Yang et al., 2008; Tang et al., 2006 ; Ji et al., 2011). We intended to prepare a copper(II) complex of 1-naphthyl acetate and the co-ligand pyrrolidine, but the title compound was obtained and we report its crystal strcture here.

The pyrrolidine ring adopts an envelope conformation, with C1C as the flap atom, and the dihedral angle between the planes of the two naphthalene ring systems is 8.34 (10)° (Fig. 1). The crystal structure is stabilized by intermolecular O—H···O and N—H···O hydrogen bond interactions (Fig. 2 and Table 1).

Experimental

The title compound was synthesized by the reaction of 1-naphthylacetic acid (93 mg, 0.5 mmol), pyrrolidine (17.78 mg, 0.25 mmol) and cupric acetate (100 mg, 0.5 mmol), in 16 ml of a water-ethanol (2:1) mixture under solvothermal conditions. The mixture was homogenized and transferred to a sealed Teflon-lined solvothermal bomb (volume 25 ml) and heated to 120°C for three days. After cooling, colorless crystals of the title compound were obtained.