5-Hy-droxy-indan-1-one.

In the title compound (5HIN), C(9)H(8)O(2), is perfectly planar as all atoms, except the H atoms of both CH(2) groups, lie on a crystallographic mirror plane. In the crystal, mol-ecules are linked by strong inter-molecular O-H⋯O hydrogen bonds, forming an infinite chain along [100], generating a C(8) motif.

Related literature

For the spectroscopy of the title compound, see: Magnusson et al. (1964 ▶). For the synthetic and biological applications on indanones, see: Cai et al. (2005 ▶); De Paulis et al. (1981 ▶); Howbert & Crowell (1990 ▶); Kwiecien et al. (1991 ▶). For the preparation, see: Danishefsky et al. (1979 ▶). For related structures, see: Chen et al. (2011 ▶); Li et al. (2007 ▶); Saeed & Bolte (2007 ▶). For graph-set theory, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C9H8O2

M = 148.15

Orthorhombic,

a = 13.9126 (7) Å

b = 6.7332 (4) Å

c = 7.5368 (3) Å

V = 706.02 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 297 K

0.39 × 0.30 × 0.25 mm

Data collection

Bruker SMART CCD detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T min = 0.991, T max = 1.000

2023 measured reflections

920 independent reflections

605 reflections with I > 2σ(I)

R int = 0.020

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.081

S = 1.03

920 reflections

78 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.21 e Å−3

Δρmin = −0.21 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 publication routines (Farrugia, 1999 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811010956/si2345sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811010956/si2345Isup2.hkl

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

C9H8O2	F(000) = 312
Mr = 148.15	Dx = 1.394 Mg m−3
Orthorhombic, Pnma	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2n	Cell parameters from 962 reflections
a = 13.9126 (7) Å	θ = 2.9–29.1°
b = 6.7332 (4) Å	µ = 0.10 mm−1
c = 7.5368 (3) Å	T = 297 K
V = 706.02 (6) Å3	Parallelepiped, yellow
Z = 4	0.39 × 0.30 × 0.25 mm

Bruker SMART CCD detector diffractometer	920 independent reflections
Radiation source: fine-focus sealed tube	605 reflections with I > 2σ(I)
graphite	Rint = 0.020
ω scans	θmax = 29.2°, θmin = 2.9°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −19→19
Tmin = 0.991, Tmax = 1.000	k = −9→9
2023 measured reflections	l = −10→10

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.081	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ2(Fo2) + (0.040P)2] where P = (Fo2 + 2Fc2)/3
920 reflections	(Δ/σ)max = 0.001
78 parameters	Δρmax = 0.21 e Å−3
0 restraints	Δρmin = −0.21 e Å−3

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	0.80931 (8)	0.2500	0.98929 (18)	0.0531 (4)
O2	0.34842 (9)	0.2500	0.85642 (18)	0.0454 (4)
H2A	0.3393 (16)	0.2500	0.728 (3)	0.078 (8)*
C1	0.73075 (12)	0.2500	1.0631 (2)	0.0342 (4)
C2	0.71859 (13)	0.2500	1.2617 (2)	0.0380 (5)
H2B	0.7500 (10)	0.1348 (15)	1.3102 (18)	0.058 (4)*
C3	0.61036 (12)	0.2500	1.2963 (2)	0.0354 (4)
H3A	0.5894 (8)	0.1337 (17)	1.3668 (17)	0.050 (4)*
C4	0.56635 (11)	0.2500	1.1138 (2)	0.0283 (4)
C5	0.63619 (10)	0.2500	0.9813 (2)	0.0284 (4)
C6	0.60937 (11)	0.2500	0.8033 (2)	0.0336 (4)
H6A	0.6558	0.2500	0.7146	0.040*
C7	0.51359 (12)	0.2500	0.7604 (2)	0.0343 (4)
H7A	0.4949	0.2500	0.6419	0.041*
C8	0.44362 (12)	0.2500	0.8945 (2)	0.0311 (4)
C9	0.47000 (12)	0.2500	1.0715 (2)	0.0320 (4)
H9A	0.4236	0.2500	1.1603	0.038*

	U11	U22	U33	U12	U13	U23
O1	0.0222 (7)	0.0992 (10)	0.0379 (7)	0.000	0.0057 (7)	0.000
O2	0.0228 (7)	0.0766 (9)	0.0369 (8)	0.000	−0.0037 (6)	0.000
C1	0.0255 (10)	0.0456 (10)	0.0315 (10)	0.000	0.0013 (8)	0.000
C2	0.0293 (11)	0.0537 (12)	0.0311 (9)	0.000	−0.0035 (8)	0.000
C3	0.0277 (10)	0.0528 (11)	0.0256 (9)	0.000	0.0005 (8)	0.000
C4	0.0254 (9)	0.0337 (9)	0.0256 (8)	0.000	0.0004 (7)	0.000
C5	0.0201 (9)	0.0386 (9)	0.0264 (9)	0.000	0.0012 (7)	0.000
C6	0.0240 (10)	0.0502 (10)	0.0264 (8)	0.000	0.0069 (8)	0.000
C7	0.0300 (10)	0.0482 (10)	0.0247 (8)	0.000	−0.0014 (8)	0.000
C8	0.0203 (9)	0.0391 (9)	0.0338 (9)	0.000	−0.0009 (8)	0.000
C9	0.0239 (10)	0.0443 (9)	0.0278 (9)	0.000	0.0054 (7)	0.000

O1—C1	1.2264 (19)	C4—C5	1.393 (2)
O2—C8	1.355 (2)	C4—C9	1.378 (2)
O2—H2A	0.97 (3)	C5—C6	1.393 (2)
C1—C5	1.453 (2)	C6—C7	1.371 (2)
C1—C2	1.506 (2)	C6—H6A	0.9300
C2—C3	1.528 (3)	C7—C8	1.403 (2)
C2—H2B	0.963 (11)	C7—H7A	0.9300
C3—C4	1.506 (2)	C8—C9	1.384 (2)
C3—H3A	0.990 (11)	C9—H9A	0.9300
C8—O2—H2A	109.8 (14)	C4—C5—C1	109.13 (14)
O1—C1—C5	127.92 (15)	C6—C5—C1	130.64 (15)
O1—C1—C2	123.42 (16)	C7—C6—C5	119.18 (15)
C5—C1—C2	108.65 (15)	C7—C6—H6A	120.4
C1—C2—C3	106.29 (15)	C5—C6—H6A	120.4
C1—C2—H2B	109.1 (8)	C6—C7—C8	120.28 (16)
C3—C2—H2B	112.5 (8)	C6—C7—H7A	119.9
C4—C3—C2	104.15 (14)	C8—C7—H7A	119.9
C4—C3—H3A	111.7 (7)	O2—C8—C9	117.62 (16)
C2—C3—H3A	112.4 (7)	O2—C8—C7	121.68 (15)
C5—C4—C9	120.87 (15)	C9—C8—C7	120.70 (16)
C5—C4—C3	111.78 (14)	C8—C9—C4	118.74 (16)
C9—C4—C3	127.35 (15)	C8—C9—H9A	120.6
C4—C5—C6	120.23 (14)	C4—C9—H9A	120.6

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2A···O1i	0.98 (2)	1.69 (2)	2.6618 (19)	173 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2A⋯O1i	0.98 (2)	1.69 (2)	2.6618 (19)	173 (2)

Symmetry code: (i) .