4-Hy­droxy­indan-1-one

Abstract

The mol­ecule of the title compound, C₉H₈O₂, is essentially planar except for the methyl­ene H atoms [maximum deviation = 0.028 (1) Å]. In the crystal, the mol­ecules are linked by classical O—H⋯O hydrogen bonds and weak C—H⋯O inter­actions 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 _r = 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) ų

• 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

• Δρ_max = 0.21 e Å⁻³

• Δρ_min = −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 ▶).

Supplementary Material

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
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) .

supplementary crystallographic information

Comment

Indanone derivatives are some of the most widely used organic compounds (Tang et al., 2011). Indanone derivatives are used as dyes and pigments (Cui et al., 2009; Li et al., 2009), intermediates in organic synthesis (Borbone et al., 2011; Borge et al., 2010; Fu & Wang, 2008; Yu et al., 2011), and exhibit a wide variety of biological activities (Sousa et al., 2011). In addition, 1-indanones were important precursors in the regiospecific synthesis of 2-fluoro-1-naphthols (Cai et al., 2005).

The molecular structure of the title compound is shown in Figure 1. The molecule is essentially planar (the maximum deviation = 0.028 (1) Å), which is consistent with previous studies (Ali et al., 2010; Chen et al., 2011a,b). In the crystal (Fig. 2), molecules are linked by intermolecular O—H···O and C—H···O hydrogen bonds (Table 1) to form an infinite one-dimensional chain along and [1 1 0 and ][1 -1 0], generating two different kinds of C(7) motifs (Bernstein et al., 1995).

Experimental

The title compound was synthesized by the hydrolation of 4-benzoyloxy-1-indanone with sodium hydroxide (Gerasov et al., 2011). Colorless parallelepiped -shaped crystals suitable for the crystallographic studies reported here were isolated over a period of five weeks by slow evaporation from a ethyl acetate solution.

Refinement

H atoms bonded to O and C atoms were located in a difference electron density map. The hydroxy H atom and the C_sp3 H atoms were freely refined, and the C_sp2 H atoms repositioned geometrically and refined using a riding model, [C—H = 0.93 Å and U_iso(H) = 1.2U_eq(C)].

Figures

Fig. 1.

The molecular structure of the title compound, showing 50% probability displacement ellipsoids.

Fig. 2.

A section of the crystal packing of the title compound, viewed along the c axis. Green and blue dashed lines denote the intermolecular O1—H1A···O2 and C2—H2A···O2 hydrogen bonds, respectively. For clarity, hydrogen atoms not involved in hydrogen bonding have been omitted.

Crystal data

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

Data collection

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

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

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	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)

Atomic displacement parameters (Ų)

	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)

Geometric parameters (Å, º)

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)

Hydrogen-bond geometry (Å, º)

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) x−1/2, y+1/2, z.