4-Hy-droxy-indan-1-one.

The mol-ecule of the title compound, C(9)H(8)O(2), is essentially planar except for the methyl-ene H atoms [maximum deviation = 0.028 (1) Å]. In the crystal, the mol-ecules are linked by classical O-H⋯O hydrogen bonds and weak C-H⋯O inter-actions into chains along [110] and [1-10].

Related literature

For the preparation of the title compound, see: Gerasov et al. (2011 ▶). For applications of indanone derivatives, see: Tang et al. (2011 ▶); Borbone et al. (2011 ▶); Borge et al. (2010 ▶); Cai et al. (2005 ▶); Cui et al. (2009 ▶); Fu & Wang (2008 ▶); Li et al. (2009 ▶); Sousa et al. (2011 ▶); Yu et al. (2011 ▶). For related structures, see: Ali et al. (2010 ▶); Chen et al. (2011a ▶,b ▶). For graph-set theory, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C9H8O2

M = 148.15

Monoclinic,

a = 13.5890 (6) Å

b = 8.6160 (3) Å

c = 13.9435 (6) Å

β = 116.738 (6)°

V = 1457.98 (13) Å3

Z = 8

Mo Kα radiation

μ = 0.10 mm−1

T = 297 K

0.63 × 0.60 × 0.38 mm

Data collection

Bruker SMART CCD detector diffractometer

6305 measured reflections

1794 independent reflections

1289 reflections with I > 2σ(I)

R int = 0.018

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.115

S = 1.06

1794 reflections

104 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.21 e Å−3

Δρmin = −0.15 e Å−3

Data collection: SMART (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); 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 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812041669/xu5628sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812041669/xu5628Isup2.hkl

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

C9H8O2	F(000) = 624
Mr = 148.15	Dx = 1.350 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 3232 reflections
a = 13.5890 (6) Å	θ = 2.8–29.2°
b = 8.6160 (3) Å	µ = 0.10 mm−1
c = 13.9435 (6) Å	T = 297 K
β = 116.738 (6)°	Parallelepiped, colorless
V = 1457.98 (13) Å3	0.63 × 0.60 × 0.38 mm
Z = 8

Bruker SMART CCD detector diffractometer	1289 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.018
Graphite monochromator	θmax = 29.2°, θmin = 2.9°
ω scans	h = −18→18
6305 measured reflections	k = −11→11
1794 independent reflections	l = −19→18

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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.115	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ2(Fo2) + (0.0704P)2] where P = (Fo2 + 2Fc2)/3
1794 reflections	(Δ/σ)max = 0.001
104 parameters	Δρmax = 0.21 e Å−3
0 restraints	Δρmin = −0.15 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	0.21183 (9)	0.05958 (13)	0.03489 (8)	0.0607 (3)
H1A	0.1454 (17)	0.116 (3)	0.0012 (17)	0.101 (6)*
O2	0.51759 (9)	−0.29276 (13)	−0.06930 (10)	0.0714 (4)
C1	0.24288 (9)	0.01208 (14)	−0.04004 (9)	0.0373 (3)
C2	0.18722 (10)	0.05169 (14)	−0.14805 (10)	0.0405 (3)
H2A	0.1252	0.1147	−0.1716	0.049*
C3	0.22258 (10)	−0.00108 (14)	−0.22117 (9)	0.0414 (3)
H3A	0.1839	0.0273	−0.2930	0.050*
C4	0.31337 (10)	−0.09427 (14)	−0.18965 (10)	0.0404 (3)
H4A	0.3372	−0.1300	−0.2386	0.049*
C5	0.36864 (9)	−0.13348 (13)	−0.08148 (9)	0.0350 (3)
C6	0.33542 (9)	−0.08162 (13)	−0.00686 (9)	0.0341 (3)
C7	0.40960 (11)	−0.13665 (16)	0.10481 (10)	0.0470 (3)
H7A	0.3686	−0.1952	0.1343	0.056*
H7B	0.4457	−0.0499	0.1519	0.056*
C8	0.49369 (11)	−0.24025 (16)	0.09019 (12)	0.0499 (4)
H8A	0.5681	−0.2036	0.1346	0.060*
H8B	0.4879	−0.3465	0.1100	0.060*
C9	0.46657 (10)	−0.23041 (14)	−0.02658 (11)	0.0445 (3)

	U11	U22	U33	U12	U13	U23
O1	0.0637 (7)	0.0832 (8)	0.0452 (6)	0.0363 (6)	0.0333 (5)	0.0071 (5)
O2	0.0529 (6)	0.0864 (8)	0.0794 (8)	0.0316 (6)	0.0337 (6)	−0.0066 (6)
C1	0.0363 (6)	0.0424 (6)	0.0357 (6)	0.0098 (5)	0.0186 (5)	0.0002 (5)
C2	0.0350 (6)	0.0421 (7)	0.0416 (7)	0.0121 (5)	0.0149 (5)	0.0066 (5)
C3	0.0460 (7)	0.0437 (7)	0.0305 (6)	0.0028 (5)	0.0135 (5)	0.0024 (5)
C4	0.0442 (7)	0.0446 (7)	0.0373 (6)	0.0016 (5)	0.0226 (6)	−0.0067 (5)
C5	0.0305 (6)	0.0354 (6)	0.0398 (6)	0.0029 (5)	0.0162 (5)	−0.0040 (4)
C6	0.0315 (6)	0.0365 (6)	0.0327 (6)	0.0047 (5)	0.0130 (5)	−0.0003 (4)
C7	0.0428 (7)	0.0557 (8)	0.0357 (7)	0.0110 (6)	0.0118 (6)	0.0040 (5)
C8	0.0353 (7)	0.0491 (7)	0.0532 (8)	0.0116 (6)	0.0091 (6)	0.0054 (6)
C9	0.0329 (6)	0.0425 (7)	0.0559 (8)	0.0069 (5)	0.0181 (6)	−0.0051 (6)

O1—C1	1.3542 (13)	C4—H4A	0.9300
O1—H1A	0.94 (2)	C5—C6	1.3814 (15)
O2—C9	1.2229 (14)	C5—C9	1.4622 (16)
C1—C6	1.3869 (15)	C6—C7	1.5011 (16)
C1—C2	1.3899 (17)	C7—C8	1.5341 (18)
C2—C3	1.3848 (16)	C7—H7A	0.9700
C2—H2A	0.9300	C7—H7B	0.9700
C3—C4	1.3683 (16)	C8—C9	1.501 (2)
C3—H3A	0.9300	C8—H8A	0.9700
C4—C5	1.3906 (16)	C8—H8B	0.9700
C1—O1—H1A	109.4 (12)	C1—C6—C7	127.94 (10)
O1—C1—C6	117.97 (10)	C5—C6—C7	112.62 (10)
O1—C1—C2	123.73 (11)	C6—C7—C8	103.81 (10)
C6—C1—C2	118.30 (10)	C6—C7—H7A	111.0
C1—C2—C3	121.15 (11)	C8—C7—H7A	111.0
C1—C2—H2A	119.4	C6—C7—H7B	111.0
C3—C2—H2A	119.4	C8—C7—H7B	111.0
C4—C3—C2	121.17 (11)	H7A—C7—H7B	109.0
C4—C3—H3A	119.4	C9—C8—C7	106.09 (10)
C2—C3—H3A	119.4	C9—C8—H8A	110.5
C3—C4—C5	117.38 (10)	C7—C8—H8A	110.5
C3—C4—H4A	121.3	C9—C8—H8B	110.5
C5—C4—H4A	121.3	C7—C8—H8B	110.5
C4—C5—C6	122.57 (10)	H8A—C8—H8B	108.7
C4—C5—C9	128.81 (10)	O2—C9—C5	125.30 (13)
C6—C5—C9	108.63 (10)	O2—C9—C8	125.95 (12)
C1—C6—C5	119.44 (10)	C5—C9—C8	108.75 (10)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···O2i	0.94 (2)	1.75 (2)	2.6918 (18)	175 (2)
C2—H2A···O2i	0.93	2.59	3.255 (2)	129

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1A⋯O2i	0.94 (2)	1.75 (2)	2.6918 (18)	175 (2)
C2—H2A⋯O2i	0.93	2.59	3.255 (2)	129

Symmetry code: (i) .