7-Hy­droxy­indan-1-one

Kew-Yu Chen; Yuh-Sheng Wen; Tzu-Chien Fang; Yuan-Jay Chang; Ming-Jen Chang

doi:10.1107/S1600536811009718

. 2011 Mar 19;67(Pt 4):o927. doi: 10.1107/S1600536811009718

7-Hydroxyindan-1-one

Kew-Yu Chen ^a,^*, Yuh-Sheng Wen ^b, Tzu-Chien Fang ^a, Yuan-Jay Chang ^b, Ming-Jen Chang ^a

PMCID: PMC3099748 PMID: 21754197

Abstract

In the title compound, C₉H₈O₂, an intramolecular O—H⋯O hydrogen bond generates an S(6) ring. The dihedral angle between the mean plane of the S(6) ring and the benzene ring is 1.89 (2)°. In the crystal, inversion-related molecules are linked by pairs of O—H⋯O hydrogen bonds, forming a cyclic dimers with R ₂ ²(12) graph-set motif. Weak intermolecular C—H⋯O_carbonyl and C—H⋯O_hydroxy hydrogen bonds link the dimers into chains along [010], generating two C(6) motifs that overlap three C atoms, forming R ₂ ²(8) ring motifs.

Related literature

For the spectroscopy and the dynamic processes related to the intramolecular proton transfer of the title compound, see: Aquino et al. (2005 ▶); Chou et al. (1991 ▶); Nagaoka et al. (1984 ▶); Nishiya et al. (1986 ▶). For its preparation, see: Tadić et al. (1988 ▶). For related structures, see: Li et al. (2007 ▶); Saeed et al. (2007 ▶). For graph-set theory, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C₉H₈O₂
M _r = 148.15
Monoclinic,
a = 7.3457 (3) Å
b = 13.3767 (5) Å
c = 7.3693 (3) Å
β = 108.584 (2)°
V = 686.36 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 100 K
0.28 × 0.24 × 0.24 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T _min = 0.676, T _max = 0.745
5437 measured reflections
1400 independent reflections
1252 reflections with I > 2σ(I)
R _int = 0.022

Refinement

R[F ² > 2σ(F ²)] = 0.033
wR(F ²) = 0.089
S = 1.04
1400 reflections
133 parameters
All H-atom parameters refined
Δρ_max = 0.28 e Å⁻³
Δρ_min = −0.18 e Å⁻³

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811009718/si2340sup1.cif

e-67-0o927-sup1.cif^{(14KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811009718/si2340Isup2.hkl

e-67-0o927-Isup2.hkl^{(67.7KB, 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⋯O1	0.880 (17)	2.182 (18)	2.899 (1)	138 (1)
O2—H2⋯O1ⁱ	0.880 (17)	2.219 (14)	2.864 (1)	130 (1)
C1—H1B⋯O2ⁱⁱ	0.985 (14)	2.519 (14)	3.478 (1)	164 (1)
C4—H4⋯O1ⁱⁱⁱ	0.964 (16)	2.527 (16)	3.467 (1)	165 (1)

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

Acknowledgments

Financial support from the National Science Council of the Republic of China is gratefully acknowledged.

supplementary crystallographic information

Comment

The excited-state intramolecular proton transfer (ESIPT) reaction of 7-hydroxy-1-indanone (7HIN) has been investigated for past decades (Aquino et al., 2005; Nagaoka et al., 1984; Nishiya et al., 1986), which incorporates transfer of a hydroxy proton to the carbonyl oxygen through a intramolecular six-membered-ring hydrogen-bonding system (Chou et al., 1991).

The ORTEP diagram of the title compound is shown in Figure 1. The indane moiety is essentially planar (r.m.s. deviation for the nine C atoms = 0.014 Å), which is consistent with previous studies (Li, et al., 2007; Saeed et al., 2007). 7HIN possesses a intramolecular six-membered ring hydrogen bond, which generates an S(6) ring motif. The dihedral angle between the mean plane of the S(6) ring and the mean plane of the benzene ring is 1.89 (2)°. This, together with 2.182 (18) Å of O2—H2···O1 distance and 138 (1)° of O2—H2—O1 (Table 1), strongly supports the S(6) ring formation. (Bernstein et al., 1995). In the crystal structure, two inversion related molecules are linked by dual O—H···O hydrogen bonds (black dashed line) to form a cyclic dimer of R₂²(12) ring system (Fig. 2). Furthermore, weak intermolecular C4—H4···O1 (green dashed line) and C1—H1B···O2 (blue dashed line) hydrogen bonds link the dimers into the chains along [0 1 0], generating two C(6) motifs that overlap three C atoms (C2, C8 and C3) to form R₂²(8) ring motifs.

Experimental

7-hydroxy-1-indanone was purchased from Sigma-Aldrich (>97% purity) and used as received without further purification. White needle-shaped crystals suitable for the crystallographic studies reported here were isolated over a period of two weeks by slow evaporation from a cyclohexane solution.