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

In the title compound, C(11)H(10)O(3), the 1-indanone unit is essentially planar (r.m.s. deviation = 0.036 Å). In the crystal, mol-ecules 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 = 190.19

Orthorhombic,

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[F 2 > 2σ(F 2)] = 0.087

wR(F 2) = 0.231

S = 1.10

2339 reflections

127 parameters

H-atom parameters constrained

Δρmax = 0.23 e Å−3

Δρmin = −0.21 e Å−3

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 ▶).

Click here for additional data file.

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

Click here for additional data file.

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

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536812041293/ff2083Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C11H10O3	F(000) = 800
Mr = 190.19	Dx = 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

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

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(Fo2) + (0.074P)2 + 2.2948P] where P = (Fo2 + 2Fc2)/3
2339 reflections	(Δ/σ)max = 0.001
127 parameters	Δρmax = 0.23 e Å−3
0 restraints	Δρmin = −0.21 e Å−3

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.

	x	y	z	Uiso*/Ueq
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*

	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)

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)

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

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) .