1-(3-Amino-1H-inden-2-yl)ethanone

Dong-Yue Hu; Zhi-Rong Qu

doi:10.1107/S1600536808033485

. 2008 Oct 31;64(Pt 11):o2239. doi: 10.1107/S1600536808033485

1-(3-Amino-1H-inden-2-yl)ethanone

Dong-Yue Hu ^a, Zhi-Rong Qu ^a,^*

PMCID: PMC2959692 PMID: 21581093

Abstract

The title compound, C₁₁H₁₁NO, was synthesized by the reaction of 2-(bromomethyl)benzonitrile and acetylacetone in the presence of KOH. In the crystal packing, molecules are linked by intermolecular N—H⋯O hydrogen bonds into chains running parallel to the b axis. Centrosymmetrically-related chains interact further through weak C—H⋯π interactions.

Related literature

For the crystal structures of related compounds, see: Choi et al. (1999 ▶); Fu & Zhao (2007 ▶).

Experimental

Crystal data

C₁₁H₁₁NO
M _r = 173.21
Monoclinic,
a = 8.1794 (4) Å
b = 10.6905 (5) Å
c = 10.5602 (6) Å
β = 93.783 (8)°
V = 921.39 (8) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 293 (2) K
0.25 × 0.16 × 0.14 mm

Data collection

Rigaku SCXmini diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ▶) T _min = 0.980, T _max = 0.989
9369 measured reflections
2108 independent reflections
1385 reflections with I > 2σ(I)
R _int = 0.049

Refinement

R[F ² > 2σ(F ²)] = 0.060
wR(F ²) = 0.171
S = 1.04
2108 reflections
119 parameters
H-atom parameters constrained
Δρ_max = 0.21 e Å⁻³
Δρ_min = −0.20 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 (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97 and PRPKAPPA (Ferguson, 1999 ▶).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808033485/rz2252sup1.cif

e-64-o2239-sup1.cif^{(14.4KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808033485/rz2252Isup2.hkl

e-64-o2239-Isup2.hkl^{(103.7KB, hkl)}

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

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

Cg1 is the centroid of the C7–C11/C13 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O2	0.86	2.17	2.766 (2)	126
N1—H1B⋯O2ⁱ	0.86	2.09	2.924 (2)	164
C2—H2B⋯Cg1ⁱⁱ	0.97	2.77	3.631 (2)	148

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

Acknowledgments

This work was supported by a Start-up Grant from Southeast University to ZRQ.

supplementary crystallographic information

Comment

In recent years, the synthesis and characterization of new ligands containing amino donor groups has received considerable attention due to the potential applications in coordination chemistry (Choi et al., 1999; Fu & Zhao, 2007). We report here the crystal structure of the title compound, which was obtained by the reaction of o-(bromomethyl)benzonitrile and acetylacetone in the presence of KOH.

In the molecule of the title compound (Fig. 1), the five-membered ring formed through the reaction is planar, and the geometric parameters are in the usual ranges. The molecular conformation is stabilized by an intramolecular N—H···O hydrogen bond (Table 1). In the crystal structure (Fig. 2), molecules are connected by intermolecular N—H···O hydrogen bonds into chains running parallel to the b axis (Table 1). Centrosymmetrically-related chains are further interacting through weak C—H···π interactions (Table 1).

Experimental

Acetylacetone (0.5 g, 0.5 mmol) and o-(bromomethyl)-benzonitrile (0.98 g, 0.5 mmol) were dissolved in methanol (30 ml) in the presence of KOH (0.28 g, 0.5 mmol) and the mixture refluxed for 24 h at 393K. After cooling to room temperature, most of the solvent was removed by vacuum filtration. Colourless crystals of the title compound suitable for X-ray diffraction analysis were obtained by slow evaporation of the remaining solvent.