5-Hy­droxy­indan-1-one

Chen, K.-Y.; Fang, T.-C.; Chang, M.-J.

doi:10.1107/S1600536811010956

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 67| Part 4| April 2011| Page o992

doi:10.1107/S1600536811010956

Open

access

5-Hydroxyindan-1-one

Kew-Yu Chen,^a ^* Tzu-Chien Fang ^a and Ming-Jen Chang ^a

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

(Received 16 March 2011; accepted 24 March 2011; online 31 March 2011)

In the title compound (5HIN), C₉H₈O₂, is perfectly planar as all atoms, except the H atoms of both CH₂ groups, lie on a crystallographic mirror plane. In the crystal, molecules are linked by strong intermolecular 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_r = 148.15
Orthorhombic, P n m a
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[F² > 2σ(F²)] = 0.037
wR(F²) = 0.081
S = 1.03
920 reflections
78 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.21 e Å⁻³
Δρ_min = −0.21 e Å⁻³

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) $[x-{\script{1\over 2}}, y, -z+{\script{3\over 2}}]$ .

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 ).

Supporting information

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

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

checkCIF report

Comment top

Acid strengths of 5- and 7-hydroxyindan-1-one have been investigated by UV-vis and ¹H NMR measurements (Magnusson et al., 1964). In addition, 1-indanones were important precursors in the regiospecific synthesis of 2-fluoro-1-naphthols (Cai et al., 2005). 5-Chloro-1-indanone was used to synthesize important biomedical compounds as anticonvulsants (Kwiecien et al., 1991), and anticholinergics (De Paulis et al., 1981), showing great activity against solid tumours (Howbert et al., 1990).

The ORTEP diagram of the title compound (5HIN) is shown in Figure 1. The complete molecule (exceptions: H2B and H3A) is perfectly planar, which is slightly different from those of previous studies on other 1-indanone derivatives. (Chen, et al., 2011; Li, et al., 2007; Saeed et al., 2007). In the crystal (Figure 2), the molecules are linked by strong intermolecular O—H···O hydrogen bonds (1.69 (2)Å of O2—H2A···O1 distance and 173 (2)° of O2—H2A—O1, Table 1) to form an infinite one-dimensional chain along [1 0 0], generating a C(8) motif (Bernstein et al., 1995).

Related literature top

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 et al. (2007). For graph-set theory, see: Bernstein et al. (1995).

Experimental top

5-Hydroxyindan-1-one was purchased from Sigma-Aldrich (>95% purity) and used as received without further purification. Yellow needle-shaped crystals suitable for the crystallographic studies reported here were isolated over a period of three weeks by slow evaporation from a ethyl acetate solution.

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); 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 b axis. For clarity, hydrogen atoms not involved in hydrogen bonding have been omitted.

5-Hydroxyindan-1-one top

Crystal data top

C₉H₈O₂	F(000) = 312
M_r = 148.15	D_x = 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

Data collection top

Bruker SMART CCD detector diffractometer	920 independent reflections
Radiation source: fine-focus sealed tube	605 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.020
ω scans	θ_max = 29.2°, θ_min = 2.9°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −19→19
T_min = 0.991, T_max = 1.000	k = −9→9
2023 measured reflections	l = −10→10

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)] = 0.037	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(F_o²) + (0.040P)²] where P = (F_o² + 2F_c²)/3
920 reflections	(Δ/σ)_max = 0.001
78 parameters	Δρ_max = 0.21 e Å⁻³
0 restraints	Δρ_min = −0.21 e Å⁻³

Crystal data top

C₉H₈O₂	V = 706.02 (6) Å³
M_r = 148.15	Z = 4
Orthorhombic, Pnma	Mo Kα radiation
a = 13.9126 (7) Å	µ = 0.10 mm⁻¹
b = 6.7332 (4) Å	T = 297 K
c = 7.5368 (3) Å	0.39 × 0.30 × 0.25 mm

Data collection top

Bruker SMART CCD detector diffractometer	920 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2001)	605 reflections with I > 2σ(I)
T_min = 0.991, T_max = 1.000	R_int = 0.020
2023 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.037	0 restraints
wR(F²) = 0.081	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	Δρ_max = 0.21 e Å⁻³
920 reflections	Δρ_min = −0.21 e Å⁻³
78 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	0.80931 (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*

Atomic displacement parameters (Å²) top

	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

Geometric parameters (Å, º) top

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

Hydrogen-bond geometry (Å, º) top

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) x−1/2, y, −z+3/2.

Experimental details

Crystal data
Chemical formula	C₉H₈O₂
M_r	148.15
Crystal system, space group	Orthorhombic, Pnma
Temperature (K)	297
a, b, c (Å)	13.9126 (7), 6.7332 (4), 7.5368 (3)
V (Å³)	706.02 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.39 × 0.30 × 0.25

Data collection
Diffractometer	Bruker SMART CCD detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2001)
T_min, T_max	0.991, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	2023, 920, 605
R_int	0.020
(sin θ/λ)_max (Å⁻¹)	0.685

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.037, 0.081, 1.03
No. of reflections	920
No. of parameters	78
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.21, −0.21

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), 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
O2—H2A···O1ⁱ	0.98 (2)	1.69 (2)	2.6618 (19)	173 (2)

Symmetry code: (i) x−1/2, y, −z+3/2.

Acknowledgements

Financial support from the National Science Council of the Republic of China is gratefully acknowledged.

References

Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573. CrossRef CAS Web of Science Google Scholar
Bruker (2001). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Cai, X., Wu, K. & Dolbier, W. R. Jr (2005). J. Fluor. Chem. 126, 479–482. Web of Science CrossRef CAS Google Scholar
Chen, K.-Y., Wen, Y.-S., Fang, T.-C., Chang, Y.-J. & Chang, M.-J. (2011). Acta Cryst. E67, o927. Web of Science CSD CrossRef IUCr Journals Google Scholar
Danishefsky, S., Harayama, T. & Singh, R. K. (1979). J. Am. Chem. Soc. 101, 7008–7012. CrossRef CAS Google Scholar
De Paulis, T., Betts, C. R., Smith, H. E., Mobley, P. L., Marnier, D. H. & Sulser, F. (1981). J. Med. Chem. 24, 1021–1024. CrossRef CAS PubMed Web of Science Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838. CrossRef CAS IUCr Journals Google Scholar
Howbert, J. J. & Crowell, T. A. (1990). Synth. Commun. 20, 3193–3200. CrossRef CAS Google Scholar
Kwiecien, H., Jalowiczor, R., Bogdal, M., Krzywosinski, L. & Przemyk, B. (1991). Pol. J. Chem. 65, 2057–2160. CAS Google Scholar
Li, Z., Xu, J.-H., Rosli, M. M. & Fun, H.-K. (2007). Acta Cryst. E63, o3435. Web of Science CSD CrossRef IUCr Journals Google Scholar
Magnusson, L. B., Craig, C. A. & Postmus, C. Jr (1964). J. Am. Chem. Soc. 86, 3958–3961. CrossRef CAS Google Scholar
Saeed, A. & Bolte, M. (2007). Acta Cryst. E63, o2757. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar