3-Oxo-2,3-dihydro-1H-inden-4-yl acetate

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

doi:10.1107/S1600536812041293

organic compounds

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ISSN: 2056-9890

Volume 68| Part 11| November 2012| Pages o3075-o3076

doi:10.1107/S1600536812041293

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3-Oxo-2,3-dihydro-1H-inden-4-yl acetate

Hong-Yi Lin,^a Che-Wei Chang,^a Hsing-Yang Tsai,^a Ming-Hui Luo ^a and Kew-Yu Chen ^a ^*

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

(Received 27 September 2012; accepted 2 October 2012; online 6 October 2012)

In the title compound, C₁₁H₁₀O₃, the 1-indanone unit is essentially planar (r.m.s. deviation = 0.036 Å). In the crystal, molecules are linked by non-classical C—H⋯O hydrogen bonds, forming a C(6) chain along [010].

Related literature

For the preparation of the title compound, see: Rahimizadeh et al. (2010 ). For applications of indanone derivatives, see: 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 ); Tang et al. (2011 ); Yu et al. (2011 ). For related structures, see: Ali et al. (2010a ,b ,c ,d ); Chen et al. (2011a ,b ). For C—H⋯O hydrogen bonds, see: Li et al. (2011a ,b ); Wang & Chen (2011 ); Xi et al. (2010 ). For graph-set theory, see: Bernstein et al. (1995 ).

Experimental

Crystal data

C₁₁H₁₀O₃
M_r = 190.19
Orthorhombic, P b c a
a = 9.8514 (10) Å
b = 8.9757 (7) Å
c = 21.917 (3) Å
V = 1938.0 (3) Å³
Z = 8
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 297 K
0.76 × 0.60 × 0.28 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001 ) T_min = 0.761, T_max = 1.000
8705 measured reflections
2339 independent reflections
1302 reflections with I > 2σ(I)
R_int = 0.036

Refinement

R[F² > 2σ(F²)] = 0.087
wR(F²) = 0.231
S = 1.10
2339 reflections
127 parameters
H-atom parameters constrained
Δρ_max = 0.23 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
C8—H8A⋯O3ⁱ	0.93	2.46	3.223 (5)	139
Symmetry code: (i) $[-x+1, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

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 publication routines (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablock I. DOI: 10.1107/S1600536812041293/ff2083sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812041293/ff2083Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812041293/ff2083Isup3.cml

checkCIF report

Comment top

Indanone derivatives are some of the most widely used organic compounds (Tang et al., 2011). They are used as pigments and dyes (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). Furthermore, 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 1-indaneone moiety is essentially planar (r.m.s. deviation = 0.036 Å), which is consistent with previous studies (Ali et al., 2010a,b,c,d; Chen et al., 2011a,b). In the crystal (Fig. 2), molecules are linked by nonclassical intermolecular C—H···O (Li et al., 2011a,b; Wang et al., 2011; Xi et al., 2010) hydrogen bonds (Table 1) to form an infinite one-dimensional chain along [010], generating a C(6) motif (Bernstein et al., 1995).

Related literature top

For the preparation of the title compound, see: Rahimizadeh et al. (2010). For applications of indanone derivatives, see: 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); Tang et al. (2011); Yu et al. (2011). For related structures, see: Ali et al. (2010a,b,c,d); Chen et al. (2011a,b). For C—H···O hydrogen bonds, see: Li et al. (2011a,b); Wang & Chen (2011); Xi et al. (2010). For graph-set theory, see: Bernstein et al. (1995).

Experimental top

The title compound was synthesized by the acetylation of 7-hydroxyindan-1-one with acetyl chloride (Rahimizadeh et al., 2010). Colorless parallelepiped-shaped crystals suitable for the crystallographic studies reported here were isolated over a period of five weeks by slow evaporation from a chloroform 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 down the a axis. Green dashed lines denote the intermolecular C8—H8A···O3 hydrogen bonds.

3-Oxo-2,3-dihydro-1H-inden-4-yl acetate top

Crystal data top

C₁₁H₁₀O₃	F(000) = 800
M_r = 190.19	D_x = 1.304 Mg m⁻³
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 2935 reflections
a = 9.8514 (10) Å	θ = 3.1–29.2°
b = 8.9757 (7) Å	µ = 0.10 mm⁻¹
c = 21.917 (3) Å	T = 297 K
V = 1938.0 (3) Å³	Parallelepiped, colourless
Z = 8	0.76 × 0.60 × 0.28 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	2339 independent reflections
Radiation source: fine-focus sealed tube	1302 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.036
ω scans	θ_max = 29.3°, θ_min = 3.2°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −13→13
T_min = 0.761, T_max = 1.000	k = −12→12
8705 measured reflections	l = −30→30

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)] = 0.087	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.231	H-atom parameters constrained
S = 1.10	w = 1/[σ²(F_o²) + (0.074P)² + 2.2948P] where P = (F_o² + 2F_c²)/3
2339 reflections	(Δ/σ)_max = 0.001
127 parameters	Δρ_max = 0.23 e Å⁻³
0 restraints	Δρ_min = −0.21 e Å⁻³

Crystal data top

C₁₁H₁₀O₃	V = 1938.0 (3) Å³
M_r = 190.19	Z = 8
Orthorhombic, Pbca	Mo Kα radiation
a = 9.8514 (10) Å	µ = 0.10 mm⁻¹
b = 8.9757 (7) Å	T = 297 K
c = 21.917 (3) Å	0.76 × 0.60 × 0.28 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	2339 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2001)	1302 reflections with I > 2σ(I)
T_min = 0.761, T_max = 1.000	R_int = 0.036
8705 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.087	0 restraints
wR(F²) = 0.231	H-atom parameters constrained
S = 1.10	Δρ_max = 0.23 e Å⁻³
2339 reflections	Δρ_min = −0.21 e Å⁻³
127 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	0.4675 (3)	−0.1591 (3)	0.54019 (14)	0.0748 (9)
O2	0.4074 (2)	0.0430 (2)	0.64503 (12)	0.0495 (7)
O3	0.4063 (3)	−0.1886 (3)	0.68244 (16)	0.0790 (10)
C1	0.6245 (3)	−0.0223 (3)	0.60176 (15)	0.0398 (8)
C2	0.5807 (4)	−0.1175 (4)	0.55084 (17)	0.0525 (9)
C3	0.7066 (5)	−0.1530 (5)	0.5139 (2)	0.0708 (12)
H3A	0.7156	−0.2598	0.5086	0.085*
H3B	0.7013	−0.1067	0.4740	0.085*
C4	0.8266 (4)	−0.0918 (5)	0.5494 (2)	0.0703 (13)
H4A	0.8833	−0.1720	0.5645	0.084*
H4B	0.8812	−0.0269	0.5239	0.084*
C5	0.7649 (3)	−0.0065 (4)	0.60117 (17)	0.0495 (9)
C6	0.8271 (4)	0.0804 (5)	0.6447 (2)	0.0670 (12)
H6A	0.9208	0.0928	0.6442	0.080*
C7	0.7502 (5)	0.1487 (5)	0.6887 (2)	0.0715 (12)
H7A	0.7929	0.2063	0.7183	0.086*
C8	0.6107 (4)	0.1338 (4)	0.68999 (18)	0.0566 (10)
H8A	0.5596	0.1815	0.7198	0.068*
C9	0.5494 (3)	0.0480 (3)	0.64677 (16)	0.0398 (8)
C10	0.3463 (4)	−0.0857 (4)	0.66149 (19)	0.0551 (10)
C11	0.1978 (4)	−0.0793 (5)	0.6504 (3)	0.0788 (14)
H11A	0.1572	−0.1721	0.6623	0.118*
H11B	0.1813	−0.0620	0.6078	0.118*
H11C	0.1590	0.0002	0.6739	0.118*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0656 (19)	0.0770 (19)	0.082 (2)	−0.0191 (16)	−0.0143 (16)	−0.0153 (16)
O2	0.0343 (13)	0.0359 (12)	0.0784 (18)	0.0037 (10)	0.0070 (12)	0.0055 (12)
O3	0.0662 (19)	0.0619 (18)	0.109 (3)	0.0096 (15)	0.0190 (18)	0.0358 (17)
C1	0.0376 (17)	0.0323 (15)	0.0494 (19)	0.0003 (13)	−0.0006 (15)	0.0039 (14)
C2	0.059 (2)	0.0463 (19)	0.052 (2)	0.0001 (18)	−0.0060 (19)	0.0029 (17)
C3	0.083 (3)	0.065 (3)	0.065 (3)	0.019 (2)	0.014 (2)	−0.004 (2)
C4	0.055 (2)	0.066 (3)	0.090 (3)	0.011 (2)	0.024 (2)	0.000 (2)
C5	0.0359 (18)	0.0455 (18)	0.067 (2)	0.0046 (15)	0.0031 (17)	0.0047 (17)
C6	0.039 (2)	0.064 (2)	0.098 (3)	−0.0033 (19)	−0.014 (2)	−0.001 (2)
C7	0.065 (3)	0.065 (3)	0.084 (3)	−0.005 (2)	−0.025 (2)	−0.021 (2)
C8	0.057 (2)	0.055 (2)	0.058 (2)	0.0073 (19)	−0.0038 (19)	−0.0119 (19)
C9	0.0329 (17)	0.0351 (15)	0.051 (2)	0.0057 (13)	−0.0009 (14)	0.0054 (15)
C10	0.047 (2)	0.048 (2)	0.071 (3)	0.0038 (17)	0.0154 (19)	0.0047 (19)
C11	0.048 (2)	0.065 (3)	0.123 (4)	−0.005 (2)	0.012 (3)	0.003 (3)

Geometric parameters (Å, º) top

O1—C2	1.200 (4)	C4—H4B	0.9700
O2—C10	1.351 (4)	C5—C6	1.376 (6)
O2—C9	1.399 (4)	C6—C7	1.371 (6)
O3—C10	1.189 (4)	C6—H6A	0.9300
C1—C5	1.391 (5)	C7—C8	1.381 (6)
C1—C9	1.385 (4)	C7—H7A	0.9300
C1—C2	1.470 (5)	C8—C9	1.362 (5)
C2—C3	1.514 (6)	C8—H8A	0.9300
C3—C4	1.518 (6)	C10—C11	1.484 (5)
C3—H3A	0.9700	C11—H11A	0.9600
C3—H3B	0.9700	C11—H11B	0.9600
C4—C5	1.497 (5)	C11—H11C	0.9600
C4—H4A	0.9700

C10—O2—C9	117.7 (3)	C5—C6—C7	119.7 (4)
C5—C1—C9	119.4 (3)	C5—C6—H6A	120.2
C5—C1—C2	110.1 (3)	C7—C6—H6A	120.2
C9—C1—C2	130.5 (3)	C6—C7—C8	121.4 (4)
O1—C2—C1	127.0 (4)	C6—C7—H7A	119.3
O1—C2—C3	126.3 (4)	C8—C7—H7A	119.3
C1—C2—C3	106.7 (3)	C9—C8—C7	118.8 (4)
C4—C3—C2	106.7 (3)	C9—C8—H8A	120.6
C4—C3—H3A	110.4	C7—C8—H8A	120.6
C2—C3—H3A	110.4	C8—C9—C1	121.1 (3)
C4—C3—H3B	110.4	C8—C9—O2	118.7 (3)
C2—C3—H3B	110.4	C1—C9—O2	120.0 (3)
H3A—C3—H3B	108.6	O3—C10—O2	123.1 (3)
C5—C4—C3	104.9 (3)	O3—C10—C11	125.7 (4)
C5—C4—H4A	110.8	O2—C10—C11	111.2 (3)
C3—C4—H4A	110.8	C10—C11—H11A	109.5
C5—C4—H4B	110.8	C10—C11—H11B	109.5
C3—C4—H4B	110.8	H11A—C11—H11B	109.5
H4A—C4—H4B	108.8	C10—C11—H11C	109.5
C6—C5—C1	119.6 (4)	H11A—C11—H11C	109.5
C6—C5—C4	129.4 (4)	H11B—C11—H11C	109.5
C1—C5—C4	111.0 (3)

C5—C1—C2—O1	176.0 (4)	C4—C5—C6—C7	−179.7 (4)
C9—C1—C2—O1	−3.9 (6)	C5—C6—C7—C8	−0.8 (7)
C5—C1—C2—C3	−4.2 (4)	C6—C7—C8—C9	0.6 (7)
C9—C1—C2—C3	175.9 (3)	C7—C8—C9—C1	−0.6 (6)
O1—C2—C3—C4	−173.2 (4)	C7—C8—C9—O2	−174.7 (3)
C1—C2—C3—C4	7.0 (4)	C5—C1—C9—C8	0.8 (5)
C2—C3—C4—C5	−7.0 (4)	C2—C1—C9—C8	−179.3 (3)
C9—C1—C5—C6	−1.0 (5)	C5—C1—C9—O2	174.8 (3)
C2—C1—C5—C6	179.1 (3)	C2—C1—C9—O2	−5.2 (5)
C9—C1—C5—C4	179.6 (3)	C10—O2—C9—C8	−110.5 (4)
C2—C1—C5—C4	−0.4 (4)	C10—O2—C9—C1	75.4 (4)
C3—C4—C5—C6	−174.7 (4)	C9—O2—C10—O3	7.1 (6)
C3—C4—C5—C1	4.7 (5)	C9—O2—C10—C11	−173.3 (3)
C1—C5—C6—C7	1.0 (6)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8A···O3ⁱ	0.93	2.46	3.223 (5)	139

Symmetry code: (i) −x+1, y+1/2, −z+3/2.

Experimental details

Crystal data
Chemical formula	C₁₁H₁₀O₃
M_r	190.19
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	297
a, b, c (Å)	9.8514 (10), 8.9757 (7), 21.917 (3)
V (Å³)	1938.0 (3)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.76 × 0.60 × 0.28

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2001)
T_min, T_max	0.761, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	8705, 2339, 1302
R_int	0.036
(sin θ/λ)_max (Å⁻¹)	0.688

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.087, 0.231, 1.10
No. of reflections	2339
No. of parameters	127
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.23, −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
C8—H8A···O3ⁱ	0.93	2.46	3.223 (5)	139

Symmetry code: (i) −x+1, y+1/2, −z+3/2.

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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