7-Hy­droxy­indan-1-one

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

doi:10.1107/S1600536811009718

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 67| Part 4| April 2011| Page o927

doi:10.1107/S1600536811009718

Open

access

7-Hydroxyindan-1-one

Kew-Yu Chen,^a ^* Yuh-Sheng Wen,^b Tzu-Chien Fang,^a Yuan-Jay Chang ^b and Ming-Jen Chang ^a

^aDepartment of Chemical Engineering, Feng Chia University, 40724 Taichung, Taiwan, and ^bInstitute of Chemistry, Academia Sinica, 115 Taipei, Taiwan
^*Correspondence e-mail: kyuchen@fcu.edu.tw

(Received 24 February 2011; accepted 15 March 2011; online 19 March 2011)

In the title compound, C₉H₈O₂, an intramolecular O—H⋯O hydrogen bond generates an S(6) ring. The dihedral angle between the mean plane of the S(6) ring and the benzene ring is 1.89 (2)°. In the crystal, inversion-related molecules are linked by pairs of O—H⋯O hydrogen bonds, forming a cyclic dimers with R₂²(12) graph-set motif. Weak intermolecular C—H⋯O_carbonyl and C—H⋯O_hydroxy hydrogen bonds link the dimers into chains along [010], generating two C(6) motifs that overlap three C atoms, forming R₂²(8) ring motifs.

Related literature

For the spectroscopy and the dynamic processes related to the intramolecular proton transfer of the title compound, see: Aquino et al. (2005 ); Chou et al. (1991 ); Nagaoka et al. (1984 ); Nishiya et al. (1986 ). For its preparation, see: Tadić et al. (1988 ). For related structures, see: Li et al. (2007 ); Saeed et al. (2007 ). For graph-set theory, see: Bernstein et al. (1995 ).

Experimental

Crystal data

C₉H₈O₂
M_r = 148.15
Monoclinic, P 2₁ /n
a = 7.3457 (3) Å
b = 13.3767 (5) Å
c = 7.3693 (3) Å
β = 108.584 (2)°
V = 686.36 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 100 K
0.28 × 0.24 × 0.24 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001 ) T_min = 0.676, T_max = 0.745
5437 measured reflections
1400 independent reflections
1252 reflections with I > 2σ(I)
R_int = 0.022

Refinement

R[F² > 2σ(F²)] = 0.033
wR(F²) = 0.089
S = 1.04
1400 reflections
133 parameters
All H-atom parameters refined
Δρ_max = 0.28 e Å⁻³
Δρ_min = −0.18 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯O1	0.880 (17)	2.182 (18)	2.899 (1)	138 (1)
O2—H2⋯O1ⁱ	0.880 (17)	2.219 (14)	2.864 (1)	130 (1)
C1—H1B⋯O2ⁱⁱ	0.985 (14)	2.519 (14)	3.478 (1)	164 (1)
C4—H4⋯O1ⁱⁱⁱ	0.964 (16)	2.527 (16)	3.467 (1)	165 (1)
Symmetry codes: (i) -x, -y+1, -z+1; (ii) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (iii) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

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 (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811009718/si2340sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811009718/si2340Isup2.hkl

checkCIF report

Comment top

The excited-state intramolecular proton transfer (ESIPT) reaction of 7-hydroxy-1-indanone (7HIN) has been investigated for past decades (Aquino et al., 2005; Nagaoka et al., 1984; Nishiya et al., 1986), which incorporates transfer of a hydroxy proton to the carbonyl oxygen through a intramolecular six-membered-ring hydrogen-bonding system (Chou et al., 1991).

The ORTEP diagram of the title compound is shown in Figure 1. The indane moiety is essentially planar (r.m.s. deviation for the nine C atoms = 0.014 Å), which is consistent with previous studies (Li, et al., 2007; Saeed et al., 2007). 7HIN possesses a intramolecular six-membered ring hydrogen bond, which generates an S(6) ring motif. The dihedral angle between the mean plane of the S(6) ring and the mean plane of the benzene ring is 1.89 (2)°. This, together with 2.182 (18) Å of O2—H2···O1 distance and 138 (1)° of O2—H2—O1 (Table 1), strongly supports the S(6) ring formation. (Bernstein et al., 1995). In the crystal structure, two inversion related molecules are linked by dual O—H···O hydrogen bonds (black dashed line) to form a cyclic dimer of R₂²(12) ring system (Fig. 2). Furthermore, weak intermolecular C4—H4···O1 (green dashed line) and C1—H1B···O2 (blue dashed line) hydrogen bonds link the dimers into the chains along [0 1 0], generating two C(6) motifs that overlap three C atoms (C2, C8 and C3) to form R₂²(8) ring motifs.

Related literature top

For the spectroscopy and dynamics of 7HIN, see: Aquino et al. (2005); Chou et al. (1991); Nagaoka et al. (1984); Nishiya et al. (1986). For the preparation of 7HIN, see: Tadić et al. (1988). For related structures, see: Li et al. (2007); Saeed et al. (2007). For graph-set theory, see: Bernstein et al. (1995).

Experimental top

7-hydroxy-1-indanone was purchased from Sigma-Aldrich (>97% purity) and used as received without further purification. White needle-shaped crystals suitable for the crystallographic studies reported here were isolated over a period of two weeks by slow evaporation from a cyclohexane 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 (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 down the a axis.

7-Hydroxyindan-1-one top

Crystal data top

C₉H₈O₂	F(000) = 312
M_r = 148.15	D_x = 1.434 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2865 reflections
a = 7.3457 (3) Å	θ = 3.3–26.4°
b = 13.3767 (5) Å	µ = 0.10 mm⁻¹
c = 7.3693 (3) Å	T = 100 K
β = 108.584 (2)°	Prism, colourless
V = 686.36 (5) Å³	0.28 × 0.24 × 0.24 mm
Z = 4

Data collection top

Bruker SMART CCD area-detector diffractometer	1400 independent reflections
Radiation source: fine-focus sealed tube	1252 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.022
ϕ and ω scans	θ_max = 26.4°, θ_min = 3.1°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −9→9
T_min = 0.676, T_max = 0.745	k = −16→16
5437 measured reflections	l = −9→7

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.033	All H-atom parameters refined
wR(F²) = 0.089	w = 1/[σ²(F_o²) + (0.0465P)² + 0.2373P] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max < 0.001
1400 reflections	Δρ_max = 0.28 e Å⁻³
133 parameters	Δρ_min = −0.18 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.014 (4)

Crystal data top

C₉H₈O₂	V = 686.36 (5) Å³
M_r = 148.15	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 7.3457 (3) Å	µ = 0.10 mm⁻¹
b = 13.3767 (5) Å	T = 100 K
c = 7.3693 (3) Å	0.28 × 0.24 × 0.24 mm
β = 108.584 (2)°

Data collection top

Bruker SMART CCD area-detector diffractometer	1400 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2001)	1252 reflections with I > 2σ(I)
T_min = 0.676, T_max = 0.745	R_int = 0.022
5437 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.033	0 restraints
wR(F²) = 0.089	All H-atom parameters refined
S = 1.04	Δρ_max = 0.28 e Å⁻³
1400 reflections	Δρ_min = −0.18 e Å⁻³
133 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	0.08166 (12)	0.42309 (6)	0.66091 (12)	0.0198 (2)
O2	0.23230 (12)	0.62427 (6)	0.67482 (12)	0.0187 (2)
C1	0.13603 (16)	0.35050 (9)	0.97988 (17)	0.0164 (3)
C2	0.14647 (15)	0.42957 (8)	0.83566 (17)	0.0147 (3)
C3	0.28549 (15)	0.60687 (8)	0.86582 (17)	0.0141 (3)
C4	0.38227 (16)	0.68108 (9)	0.99239 (17)	0.0158 (3)
C5	0.43377 (16)	0.66351 (9)	1.18845 (17)	0.0168 (3)
C6	0.39144 (16)	0.57428 (9)	1.26467 (17)	0.0168 (3)
C7	0.23864 (17)	0.39569 (9)	1.17926 (18)	0.0170 (3)
C8	0.24541 (15)	0.51652 (8)	0.94170 (16)	0.0139 (3)
C9	0.29761 (15)	0.49992 (8)	1.13835 (17)	0.0143 (3)
H1A	0.001 (2)	0.3364 (10)	0.9591 (19)	0.019 (3)*
H1B	0.1971 (19)	0.2884 (10)	0.9566 (19)	0.019 (3)*
H2	0.164 (2)	0.5745 (14)	0.609 (2)	0.044 (5)*
H4	0.414 (2)	0.7437 (12)	0.945 (2)	0.026 (4)*
H5	0.5008 (19)	0.7159 (10)	1.2762 (19)	0.019 (3)*
H6	0.425 (2)	0.5649 (11)	1.398 (2)	0.024 (4)*
H7A	0.154 (2)	0.3975 (11)	1.264 (2)	0.024 (4)*
H7B	0.354 (2)	0.3563 (10)	1.250 (2)	0.021 (4)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0216 (5)	0.0187 (5)	0.0167 (5)	−0.0005 (3)	0.0025 (4)	−0.0018 (3)
O2	0.0228 (5)	0.0171 (4)	0.0146 (5)	−0.0036 (3)	0.0038 (3)	0.0006 (3)
C1	0.0153 (6)	0.0142 (6)	0.0200 (6)	0.0005 (4)	0.0061 (5)	0.0003 (5)
C2	0.0113 (5)	0.0144 (6)	0.0187 (6)	0.0021 (4)	0.0051 (4)	−0.0008 (4)
C3	0.0117 (5)	0.0157 (6)	0.0151 (6)	0.0024 (4)	0.0043 (4)	0.0009 (4)
C4	0.0140 (5)	0.0130 (5)	0.0204 (7)	0.0002 (4)	0.0057 (5)	0.0005 (4)
C5	0.0143 (5)	0.0153 (6)	0.0195 (6)	0.0006 (4)	0.0035 (5)	−0.0044 (5)
C6	0.0159 (6)	0.0198 (6)	0.0141 (6)	0.0024 (4)	0.0037 (5)	−0.0003 (5)
C7	0.0178 (6)	0.0154 (6)	0.0180 (6)	0.0008 (4)	0.0059 (5)	0.0019 (5)
C8	0.0110 (5)	0.0140 (5)	0.0170 (6)	0.0017 (4)	0.0050 (4)	−0.0010 (4)
C9	0.0118 (5)	0.0145 (6)	0.0173 (6)	0.0033 (4)	0.0054 (4)	0.0007 (4)

Geometric parameters (Å, º) top

O1—C2	1.2255 (14)	C4—C5	1.3919 (17)
O2—C3	1.3556 (14)	C4—H4	0.962 (16)
O2—H2	0.883 (19)	C5—C6	1.3958 (17)
C1—C2	1.5185 (16)	C5—H5	0.974 (14)
C1—C7	1.5448 (17)	C6—C9	1.3864 (16)
C1—H1A	0.976 (15)	C6—H6	0.945 (15)
C1—H1B	0.984 (14)	C7—C9	1.5184 (16)
C2—C8	1.4594 (15)	C7—H7A	1.011 (14)
C3—C4	1.3922 (16)	C7—H7B	0.993 (14)
C3—C8	1.4017 (16)	C8—C9	1.3937 (16)

C3—O2—H2	111.7 (11)	C4—C5—H5	118.7 (8)
C2—C1—C7	105.96 (9)	C6—C5—H5	118.6 (8)
C2—C1—H1A	107.5 (8)	C9—C6—C5	118.04 (11)
C7—C1—H1A	112.9 (8)	C9—C6—H6	121.0 (9)
C2—C1—H1B	109.8 (8)	C5—C6—H6	120.9 (9)
C7—C1—H1B	112.6 (8)	C9—C7—C1	104.72 (9)
H1A—C1—H1B	107.9 (11)	C9—C7—H7A	111.8 (8)
O1—C2—C8	125.41 (11)	C1—C7—H7A	112.6 (8)
O1—C2—C1	126.65 (10)	C9—C7—H7B	110.0 (8)
C8—C2—C1	107.94 (10)	C1—C7—H7B	111.6 (8)
O2—C3—C4	119.33 (10)	H7A—C7—H7B	106.3 (11)
O2—C3—C8	122.32 (10)	C9—C8—C3	121.94 (10)
C4—C3—C8	118.35 (11)	C9—C8—C2	110.78 (10)
C5—C4—C3	119.14 (11)	C3—C8—C2	127.28 (11)
C5—C4—H4	120.3 (9)	C6—C9—C8	119.80 (11)
C3—C4—H4	120.5 (9)	C6—C9—C7	129.62 (11)
C4—C5—C6	122.71 (11)	C8—C9—C7	110.57 (10)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O1	0.880 (17)	2.182 (18)	2.899 (1)	138 (1)
O2—H2···O1ⁱ	0.880 (17)	2.219 (14)	2.864 (1)	130 (1)
C1—H1B···O2ⁱⁱ	0.985 (14)	2.519 (14)	3.478 (1)	164 (1)
C4—H4···O1ⁱⁱⁱ	0.964 (16)	2.527 (16)	3.467 (1)	165 (1)

Symmetry codes: (i) −x, −y+1, −z+1; (ii) −x+1/2, y−1/2, −z+3/2; (iii) −x+1/2, y+1/2, −z+3/2.

Experimental details

Crystal data
Chemical formula	C₉H₈O₂
M_r	148.15
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	100
a, b, c (Å)	7.3457 (3), 13.3767 (5), 7.3693 (3)
β (°)	108.584 (2)
V (Å³)	686.36 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.28 × 0.24 × 0.24

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2001)
T_min, T_max	0.676, 0.745
No. of measured, independent and observed [I > 2σ(I)] reflections	5437, 1400, 1252
R_int	0.022
(sin θ/λ)_max (Å⁻¹)	0.625

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.033, 0.089, 1.04
No. of reflections	1400
No. of parameters	133
H-atom treatment	All H-atom parameters refined
Δρ_max, Δρ_min (e Å⁻³)	0.28, −0.18

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O1	0.880 (17)	2.182 (18)	2.899 (1)	138 (1)
O2—H2···O1ⁱ	0.880 (17)	2.219 (14)	2.864 (1)	130 (1)
C1—H1B···O2ⁱⁱ	0.985 (14)	2.519 (14)	3.478 (1)	164 (1)
C4—H4···O1ⁱⁱⁱ	0.964 (16)	2.527 (16)	3.467 (1)	165 (1)

Symmetry codes: (i) −x, −y+1, −z+1; (ii) −x+1/2, y−1/2, −z+3/2; (iii) −x+1/2, y+1/2, −z+3/2.

Acknowledgements

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

References

Aquino, A. J. A., Lischka, H. & Hättig, C. (2005). J. Phys. Chem. A, 109, 3201–3208. Web of Science CrossRef PubMed CAS Google Scholar
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
Chou, P.-T., Martinez, M. L. & Studer, S. L. (1991). J. Phys. Chem. 95, 10306–10310. CrossRef CAS 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
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
Nagaoka, S., Hirota, N., Sumitani, M., Yoshihara, K., Lipczynska-Kochany, E. & Iwamura, H. (1984). J. Am. Chem. Soc. 106, 6913–6916. CrossRef CAS Google Scholar
Nishiya, T., Yamauchi, S., Hirota, N., Fujiwara, Y. & Itoh, M. (1986). J. Am. Chem. Soc. 108, 3880–3884. 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
Tadić, D., Cassels, B. K. & Cavé, A. (1988). Heterocycles, 27, 407–421. Google Scholar