4-Hy­droxy­indan-1-one

Chang, C.-W.; Fang, S.-K.; Luo, M.-H.; Tsai, H.-Y.; Chen, K.-Y.

doi:10.1107/S1600536812041669

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 68| Part 11| November 2012| Page o3097

doi:10.1107/S1600536812041669

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4-Hydroxyindan-1-one

Che-Wei Chang,^a Sin-Kai Fang,^a Ming-Hui Luo,^a Hsing-Yang Tsai ^a and Kew-Yu Chen ^a ^*

^aDepartment of Chemical Engineering, Feng Chia University, 40724 Taichung, Taiwan
^*Correspondence e-mail: kyuchen@fcu.edu.tw

(Received 2 October 2012; accepted 5 October 2012; online 10 October 2012)

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, C 2/c
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[F² > 2σ(F²)] = 0.040
wR(F²) = 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

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) $[x-{\script{1\over 2}}, y+{\script{1\over 2}}, z]$ .

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 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812041669/xu5628sup1.cif

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

checkCIF report

Comment top

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).

Related literature top

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 top

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.

Computing details top

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

Figures top

	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.

4-Hydroxyindan-1-one top

Crystal data top

C₉H₈O₂	F(000) = 624
M_r = 148.15	D_x = 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 top

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

Refinement top

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(F_o²) + (0.0704P)²] where P = (F_o² + 2F_c²)/3
1794 reflections	(Δ/σ)_max = 0.001
104 parameters	Δρ_max = 0.21 e Å⁻³
0 restraints	Δρ_min = −0.15 e Å⁻³

Crystal data top

C₉H₈O₂	V = 1457.98 (13) Å³
M_r = 148.15	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 13.5890 (6) Å	µ = 0.10 mm⁻¹
b = 8.6160 (3) Å	T = 297 K
c = 13.9435 (6) Å	0.63 × 0.60 × 0.38 mm
β = 116.738 (6)°

Data collection top

Bruker SMART CCD detector diffractometer	1289 reflections with I > 2σ(I)
6305 measured reflections	R_int = 0.018
1794 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.040	0 restraints
wR(F²) = 0.115	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	Δρ_max = 0.21 e Å⁻³
1794 reflections	Δρ_min = −0.15 e Å⁻³
104 parameters

Special details top

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 (Å²) top

	x	y	z	U_iso*/U_eq
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 (Å²) top

	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) top

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) top

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.

Experimental details

Crystal data
Chemical formula	C₉H₈O₂
M_r	148.15
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	297
a, b, c (Å)	13.5890 (6), 8.6160 (3), 13.9435 (6)
β (°)	116.738 (6)
V (Å³)	1457.98 (13)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.63 × 0.60 × 0.38

Data collection
Diffractometer	Bruker SMART CCD detector diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	6305, 1794, 1289
R_int	0.018
(sin θ/λ)_max (Å⁻¹)	0.686

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.040, 0.115, 1.06
No. of reflections	1794
No. of parameters	104
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.21, −0.15

Computer programs: SMART (Bruker, 2005), SAINT (Bruker, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), WinGX publication routines (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top

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.

Acknowledgements

This work was supported by the National Science Council (grant No. NSC 101–2113-M-035–001-MY2) and Feng Chia University in Taiwan. The authors appreciate the Precision Instrument Support Center of Feng Chia University in providing fabrication and measurement facilities.

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