7-Meth-oxy-indan-1-one.

In the title compound, C(10)H(10)O(2), the 1-indanone unit is essentially planar (r.m.s. deviation = 0.028 Å). In the crystal, molecules are linked via C-H⋯O hydrogen bonds, forming layers lying parallel to the ab plane. This two-dimensional structure is stabilized by a weak C-H⋯π inter-action. A second weak C-H⋯π inter-action links the layers, forming a three-dimensional structure.

Related literature

For the preparation of the title compound, see: Li et al. (2011 ▶). For applications of indanone derivatives, see: 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 ▶). 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 ▶).

Experimental

Crystal data

C10H10O2

M = 162.18

Orthorhombic,

a = 8.5386 (7) Å

b = 10.4949 (9) Å

c = 18.8536 (16) Å

V = 1689.5 (2) Å3

Z = 8

Mo Kα radiation

μ = 0.09 mm−1

T = 297 K

0.64 × 0.55 × 0.32 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T min = 0.683, T max = 1.000

8807 measured reflections

1663 independent reflections

1278 reflections with I > 2σ(I)

R int = 0.032

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.116

S = 1.02

1663 reflections

110 parameters

H-atom parameters constrained

Δρmax = 0.20 e Å−3

Δρmin = −0.13 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, global. DOI: 10.1107/S1600536812040743/zl2507sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812040743/zl2507Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536812040743/zl2507Isup3.cml

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

C10H10O2	F(000) = 688
Mr = 162.18	Dx = 1.275 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 3629 reflections
a = 8.5386 (7) Å	θ = 2.9–26.0°
b = 10.4949 (9) Å	µ = 0.09 mm−1
c = 18.8536 (16) Å	T = 297 K
V = 1689.5 (2) Å3	Parallelepiped, colorless
Z = 8	0.64 × 0.55 × 0.32 mm

Bruker SMART CCD area-detector diffractometer	1663 independent reflections
Radiation source: fine-focus sealed tube	1278 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.032
phi and ω scans	θmax = 26.0°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −10→10
Tmin = 0.683, Tmax = 1.000	k = −12→12
8807 measured reflections	l = −16→23

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)] = 0.037	H-atom parameters constrained
wR(F2) = 0.116	w = 1/[σ2(Fo2) + (0.0636P)2 + 0.2236P] where P = (Fo2 + 2Fc2)/3
S = 1.02	(Δ/σ)max < 0.001
1663 reflections	Δρmax = 0.20 e Å−3
110 parameters	Δρmin = −0.13 e Å−3
0 restraints	Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0068 (15)

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	0.34168 (11)	0.54158 (11)	0.13950 (7)	0.0741 (4)
O2	0.07222 (10)	0.67528 (9)	0.20144 (5)	0.0545 (3)
C1	0.06609 (14)	0.50056 (11)	0.12296 (6)	0.0412 (3)
C2	0.23519 (16)	0.47945 (13)	0.11460 (7)	0.0480 (3)
C3	0.25583 (19)	0.36302 (14)	0.06788 (8)	0.0637 (4)
H3A	0.3207	0.3835	0.0272	0.076*
H3B	0.3057	0.2948	0.0943	0.076*
C4	0.09387 (18)	0.32271 (14)	0.04396 (8)	0.0606 (4)
H4A	0.0829	0.3318	−0.0070	0.073*
H4B	0.0734	0.2348	0.0568	0.073*
C5	−0.01569 (17)	0.41149 (12)	0.08242 (7)	0.0475 (3)
C6	−0.17764 (18)	0.41110 (14)	0.08112 (8)	0.0610 (4)
H6A	−0.2322	0.3522	0.0538	0.073*
C7	−0.25596 (18)	0.49998 (16)	0.12127 (8)	0.0643 (5)
H7A	−0.3649	0.5006	0.1207	0.077*
C8	−0.17749 (16)	0.58882 (14)	0.16256 (7)	0.0560 (4)
H8A	−0.2340	0.6470	0.1896	0.067*
C9	−0.01507 (15)	0.59128 (12)	0.16371 (6)	0.0431 (3)
C10	−0.0085 (2)	0.76805 (14)	0.24349 (8)	0.0662 (4)
H10A	0.0664	0.8210	0.2674	0.099*
H10B	−0.0729	0.7255	0.2779	0.099*
H10C	−0.0730	0.8198	0.2134	0.099*

	U11	U22	U33	U12	U13	U23
O1	0.0400 (6)	0.0783 (8)	0.1039 (9)	0.0010 (5)	0.0001 (6)	−0.0157 (6)
O2	0.0529 (6)	0.0558 (6)	0.0548 (6)	0.0059 (4)	−0.0009 (4)	−0.0125 (4)
C1	0.0415 (7)	0.0426 (6)	0.0395 (6)	0.0022 (5)	0.0007 (5)	0.0071 (5)
C2	0.0418 (7)	0.0503 (7)	0.0520 (7)	0.0065 (6)	0.0016 (6)	0.0054 (6)
C3	0.0651 (9)	0.0637 (9)	0.0624 (8)	0.0227 (8)	0.0009 (7)	−0.0052 (7)
C4	0.0793 (11)	0.0469 (8)	0.0555 (8)	0.0084 (7)	−0.0041 (7)	−0.0038 (6)
C5	0.0565 (8)	0.0429 (7)	0.0432 (7)	−0.0009 (6)	−0.0041 (6)	0.0052 (5)
C6	0.0548 (9)	0.0610 (9)	0.0674 (9)	−0.0121 (7)	−0.0116 (7)	0.0017 (7)
C7	0.0380 (7)	0.0802 (11)	0.0747 (10)	−0.0061 (7)	−0.0015 (7)	0.0120 (8)
C8	0.0435 (8)	0.0664 (9)	0.0583 (8)	0.0090 (6)	0.0094 (6)	0.0041 (7)
C9	0.0440 (7)	0.0458 (7)	0.0393 (6)	0.0026 (5)	0.0020 (5)	0.0043 (5)
C10	0.0800 (10)	0.0591 (8)	0.0594 (9)	0.0161 (8)	0.0020 (8)	−0.0128 (7)

O1—C2	1.2134 (17)	C4—H4B	0.9700
O2—C9	1.3560 (15)	C5—C6	1.383 (2)
O2—C10	1.4321 (16)	C6—C7	1.375 (2)
C1—C5	1.3948 (17)	C6—H6A	0.9300
C1—C9	1.4061 (17)	C7—C8	1.387 (2)
C1—C2	1.4692 (18)	C7—H7A	0.9300
C2—C3	1.517 (2)	C8—C9	1.387 (2)
C3—C4	1.515 (2)	C8—H8A	0.9300
C3—H3A	0.9700	C10—H10A	0.9600
C3—H3B	0.9700	C10—H10B	0.9600
C4—C5	1.5063 (19)	C10—H10C	0.9600
C4—H4A	0.9700
C9—O2—C10	117.90 (11)	C6—C5—C4	127.63 (13)
C5—C1—C9	120.43 (12)	C1—C5—C4	111.55 (12)
C5—C1—C2	109.40 (11)	C7—C6—C5	118.33 (13)
C9—C1—C2	130.17 (12)	C7—C6—H6A	120.8
O1—C2—C1	127.87 (13)	C5—C6—H6A	120.8
O1—C2—C3	124.79 (13)	C6—C7—C8	122.01 (14)
C1—C2—C3	107.34 (12)	C6—C7—H7A	119.0
C4—C3—C2	106.97 (12)	C8—C7—H7A	119.0
C4—C3—H3A	110.3	C7—C8—C9	120.27 (13)
C2—C3—H3A	110.3	C7—C8—H8A	119.9
C4—C3—H3B	110.3	C9—C8—H8A	119.9
C2—C3—H3B	110.3	O2—C9—C8	124.74 (12)
H3A—C3—H3B	108.6	O2—C9—C1	117.13 (11)
C5—C4—C3	104.53 (11)	C8—C9—C1	118.14 (12)
C5—C4—H4A	110.8	O2—C10—H10A	109.5
C3—C4—H4A	110.8	O2—C10—H10B	109.5
C5—C4—H4B	110.8	H10A—C10—H10B	109.5
C3—C4—H4B	110.8	O2—C10—H10C	109.5
H4A—C4—H4B	108.9	H10A—C10—H10C	109.5
C6—C5—C1	120.81 (13)	H10B—C10—H10C	109.5
C5—C1—C2—O1	176.75 (14)	C1—C5—C6—C7	−0.6 (2)
C9—C1—C2—O1	−3.7 (2)	C4—C5—C6—C7	179.00 (13)
C5—C1—C2—C3	−3.15 (14)	C5—C6—C7—C8	−0.1 (2)
C9—C1—C2—C3	176.41 (12)	C6—C7—C8—C9	0.8 (2)
O1—C2—C3—C4	−175.29 (13)	C10—O2—C9—C8	0.29 (18)
C1—C2—C3—C4	4.62 (15)	C10—O2—C9—C1	−179.75 (11)
C2—C3—C4—C5	−4.24 (15)	C7—C8—C9—O2	179.03 (12)
C9—C1—C5—C6	0.42 (18)	C7—C8—C9—C1	−0.93 (19)
C2—C1—C5—C6	−179.97 (12)	C5—C1—C9—O2	−179.63 (10)
C9—C1—C5—C4	−179.21 (11)	C2—C1—C9—O2	0.84 (18)
C2—C1—C5—C4	0.41 (14)	C5—C1—C9—C8	0.33 (17)
C3—C4—C5—C6	−177.12 (14)	C2—C1—C9—C8	−179.19 (12)
C3—C4—C5—C1	2.47 (15)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3B···O2i	0.97	2.60	3.5183 (18)	159
C7—H7A···O1ii	0.93	2.57	3.4802 (18)	167
C10—H10B···O1iii	0.96	2.59	3.486 (2)	156
C4—H4A···Cg1iv	0.97	2.80	3.6430 (16)	146
C10—H10A···Cg1v	0.96	2.82	3.6260 (16)	143

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C1/C5–C9 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3B⋯O2i	0.97	2.60	3.5183 (18)	159
C7—H7A⋯O1ii	0.93	2.57	3.4802 (18)	167
C10—H10B⋯O1iii	0.96	2.59	3.486 (2)	156
C4—H4A⋯Cg1iv	0.97	2.80	3.6430 (16)	146
C10—H10A⋯Cg1v	0.96	2.82	3.6260 (16)	143

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) .