7-Hy-droxy-indan-1-one.

In the title compound, C(9)H(8)O(2), an intra-molecular 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 mol-ecules are linked by pairs of O-H⋯O hydrogen bonds, forming a cyclic dimers with R(2) (2)(12) graph-set motif. Weak inter-molecular C-H⋯O(carbon-yl) and C-H⋯O(hy-droxy) 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 = 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

Δρmax = 0.28 e Å−3

Δρmin = −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 ▶).

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

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

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

C9H8O2	F(000) = 312
Mr = 148.15	Dx = 1.434 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2865 reflections
a = 7.3457 (3) Å	θ = 3.3–26.4°
b = 13.3767 (5) Å	µ = 0.10 mm−1
c = 7.3693 (3) Å	T = 100 K
β = 108.584 (2)°	Prism, colourless
V = 686.36 (5) Å3	0.28 × 0.24 × 0.24 mm
Z = 4

Bruker SMART CCD area-detector diffractometer	1400 independent reflections
Radiation source: fine-focus sealed tube	1252 reflections with I > 2σ(I)
graphite	Rint = 0.022
φ and ω scans	θmax = 26.4°, θmin = 3.1°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −9→9
Tmin = 0.676, Tmax = 0.745	k = −16→16
5437 measured reflections	l = −9→7

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.033	All H-atom parameters refined
wR(F2) = 0.089	w = 1/[σ2(Fo2) + (0.0465P)2 + 0.2373P] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max < 0.001
1400 reflections	Δρmax = 0.28 e Å−3
133 parameters	Δρmin = −0.18 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.014 (4)

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

	x	y	z	Uiso*/Ueq
O1	0.08166 (12)	0.42309 (6)	0.66091 (12)	0.0198 (2)
O2	0.23230 (12)	0.62427 (6)	0.67482 (12)	0.0187 (2)
C1	0.13603 (16)	0.35050 (9)	0.97988 (17)	0.0164 (3)
C2	0.14647 (15)	0.42957 (8)	0.83566 (17)	0.0147 (3)
C3	0.28549 (15)	0.60687 (8)	0.86582 (17)	0.0141 (3)
C4	0.38227 (16)	0.68108 (9)	0.99239 (17)	0.0158 (3)
C5	0.43377 (16)	0.66351 (9)	1.18845 (17)	0.0168 (3)
C6	0.39144 (16)	0.57428 (9)	1.26467 (17)	0.0168 (3)
C7	0.23864 (17)	0.39569 (9)	1.17926 (18)	0.0170 (3)
C8	0.24541 (15)	0.51652 (8)	0.94170 (16)	0.0139 (3)
C9	0.29761 (15)	0.49992 (8)	1.13835 (17)	0.0143 (3)
H1A	0.001 (2)	0.3364 (10)	0.9591 (19)	0.019 (3)*
H1B	0.1971 (19)	0.2884 (10)	0.9566 (19)	0.019 (3)*
H2	0.164 (2)	0.5745 (14)	0.609 (2)	0.044 (5)*
H4	0.414 (2)	0.7437 (12)	0.945 (2)	0.026 (4)*
H5	0.5008 (19)	0.7159 (10)	1.2762 (19)	0.019 (3)*
H6	0.425 (2)	0.5649 (11)	1.398 (2)	0.024 (4)*
H7A	0.154 (2)	0.3975 (11)	1.264 (2)	0.024 (4)*
H7B	0.354 (2)	0.3563 (10)	1.250 (2)	0.021 (4)*

	U11	U22	U33	U12	U13	U23
O1	0.0216 (5)	0.0187 (5)	0.0167 (5)	−0.0005 (3)	0.0025 (4)	−0.0018 (3)
O2	0.0228 (5)	0.0171 (4)	0.0146 (5)	−0.0036 (3)	0.0038 (3)	0.0006 (3)
C1	0.0153 (6)	0.0142 (6)	0.0200 (6)	0.0005 (4)	0.0061 (5)	0.0003 (5)
C2	0.0113 (5)	0.0144 (6)	0.0187 (6)	0.0021 (4)	0.0051 (4)	−0.0008 (4)
C3	0.0117 (5)	0.0157 (6)	0.0151 (6)	0.0024 (4)	0.0043 (4)	0.0009 (4)
C4	0.0140 (5)	0.0130 (5)	0.0204 (7)	0.0002 (4)	0.0057 (5)	0.0005 (4)
C5	0.0143 (5)	0.0153 (6)	0.0195 (6)	0.0006 (4)	0.0035 (5)	−0.0044 (5)
C6	0.0159 (6)	0.0198 (6)	0.0141 (6)	0.0024 (4)	0.0037 (5)	−0.0003 (5)
C7	0.0178 (6)	0.0154 (6)	0.0180 (6)	0.0008 (4)	0.0059 (5)	0.0019 (5)
C8	0.0110 (5)	0.0140 (5)	0.0170 (6)	0.0017 (4)	0.0050 (4)	−0.0010 (4)
C9	0.0118 (5)	0.0145 (6)	0.0173 (6)	0.0033 (4)	0.0054 (4)	0.0007 (4)

O1—C2	1.2255 (14)	C4—C5	1.3919 (17)
O2—C3	1.3556 (14)	C4—H4	0.962 (16)
O2—H2	0.883 (19)	C5—C6	1.3958 (17)
C1—C2	1.5185 (16)	C5—H5	0.974 (14)
C1—C7	1.5448 (17)	C6—C9	1.3864 (16)
C1—H1A	0.976 (15)	C6—H6	0.945 (15)
C1—H1B	0.984 (14)	C7—C9	1.5184 (16)
C2—C8	1.4594 (15)	C7—H7A	1.011 (14)
C3—C4	1.3922 (16)	C7—H7B	0.993 (14)
C3—C8	1.4017 (16)	C8—C9	1.3937 (16)
C3—O2—H2	111.7 (11)	C4—C5—H5	118.7 (8)
C2—C1—C7	105.96 (9)	C6—C5—H5	118.6 (8)
C2—C1—H1A	107.5 (8)	C9—C6—C5	118.04 (11)
C7—C1—H1A	112.9 (8)	C9—C6—H6	121.0 (9)
C2—C1—H1B	109.8 (8)	C5—C6—H6	120.9 (9)
C7—C1—H1B	112.6 (8)	C9—C7—C1	104.72 (9)
H1A—C1—H1B	107.9 (11)	C9—C7—H7A	111.8 (8)
O1—C2—C8	125.41 (11)	C1—C7—H7A	112.6 (8)
O1—C2—C1	126.65 (10)	C9—C7—H7B	110.0 (8)
C8—C2—C1	107.94 (10)	C1—C7—H7B	111.6 (8)
O2—C3—C4	119.33 (10)	H7A—C7—H7B	106.3 (11)
O2—C3—C8	122.32 (10)	C9—C8—C3	121.94 (10)
C4—C3—C8	118.35 (11)	C9—C8—C2	110.78 (10)
C5—C4—C3	119.14 (11)	C3—C8—C2	127.28 (11)
C5—C4—H4	120.3 (9)	C6—C9—C8	119.80 (11)
C3—C4—H4	120.5 (9)	C6—C9—C7	129.62 (11)
C4—C5—C6	122.71 (11)	C8—C9—C7	110.57 (10)

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)

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)

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