7-Meth­oxy­indan-1-one

Chang, Y.J.; Chen, K.-Y.

doi:10.1107/S1600536812040743

organic compounds

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ISSN: 2056-9890

Volume 68| Part 11| November 2012| Page o3063

doi:10.1107/S1600536812040743

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7-Methoxyindan-1-one

Yuan Jay Chang ^a and Kew-Yu Chen ^b ^*

^aDepartment of Chemistry, Tung Hai University, 407 Taichung, Taiwan, and ^bDepartment of Chemical Engineering, Feng Chia University, 40724 Taichung, Taiwan
^*Correspondence e-mail: kyuchen@fcu.edu.tw

(Received 26 September 2012; accepted 27 September 2012; online 3 October 2012)

In the title compound, C₁₀H₁₀O₂, 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 interaction. A second weak C—H⋯π interaction 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_r = 162.18
Orthorhombic, P b c a
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[F² > 2σ(F²)] = 0.037
wR(F²) = 0.116
S = 1.02
1663 reflections
110 parameters
H-atom parameters constrained
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.13 e Å⁻³

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⋯Cg1^iv	0.97	2.80	3.6430 (16)	146
C10—H10A⋯Cg1^v	0.96	2.82	3.6260 (16)	143
Symmetry codes: (i) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, z]$ ; (ii) x-1, y, z; (iii) $[x-{\script{1\over 2}}, y, -z+{\script{1\over 2}}]$ ; (iv) -x, -y+1, -z; (v) $[-x, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

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 I, global. DOI: 10.1107/S1600536812040743/zl2507sup1.cif

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

Supporting information file. DOI: 10.1107/S1600536812040743/zl2507Isup3.cml

checkCIF report

Comment top

Indanone and its derivatives are some of the most widely used organic compounds (Tang et al., 2011). They are used as dyes and pigments (Cui et al., 2009; Li et al., 2009), intermediates in organic synthesis (Fu & Wang, 2008; Borge et al., 2010) and exhibit a wide variety of biological activities (Sousa et al., 2011). In addition, 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 = 0.028 Å), which is consistent with previous studies (Chen et al., 2011a,b; Ali et al., 2010a,b,c,d). There are three different kinds of C—H···O (Li et al., 2011a,b; Wang et al., 2011; Xi et al., 2010) hydrogen bonds (Table 1) in the crystal structure (Figure 2). In addition, C—H···π hydrogen bonds further stabilize the crystal structure (2.80 Å for the C4—H4A···Cg1 distance and 146° for the C4—H4A—Cg1ⁱ angle; 2.82 Å for the C10—H10A···Cg1 distance and 143° for the C10—H10A—Cg1ⁱⁱ angle; Cg1 is the centroid of the C1/C5—C9 ring; symmetry codes: (i): -x, 1 - y,- z (ii): -x, 1/2 + y, 1/2 - z).

Related literature top

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: Chen et al. (2011a,b); Ali et al. (2010a,b,c,d). For C—H···O hydrogen bonds, see: Li et al. (2011a,b); Wang et al. (2011); Xi et al. (2010).

Experimental top

The title compound was synthesized by the methylation of 7-hydroxyindan-1-one with methyl iodide (Li et al., 2011). Colorless parallelepiped-shaped crystals suitable for the crystallographic study reported here were isolated over a period of six 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 along the b axis. Blue, green and red dashed lines denote the intermolecular C10—H10B···O1, C3—H3B···O2 and C7—H7A···O1 hydrogen bonds, respectively. Yellow and purple dashed lines denote the intermolecular C10—H10A···π and C4—H4A···π hydrogen bonds, respectively. Cg1 (black circles) is the centroid of the C1/C5—C9 ring. For symmetry operators, see Table 1.

7-Methoxyindan-1-one top

Crystal data top

C₁₀H₁₀O₂	F(000) = 688
M_r = 162.18	D_x = 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

Data collection top

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

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)] = 0.037	H-atom parameters constrained
wR(F²) = 0.116	w = 1/[σ²(F_o²) + (0.0636P)² + 0.2236P] where P = (F_o² + 2F_c²)/3
S = 1.02	(Δ/σ)_max < 0.001
1663 reflections	Δρ_max = 0.20 e Å⁻³
110 parameters	Δρ_min = −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)

Crystal data top

C₁₀H₁₀O₂	V = 1689.5 (2) Å³
M_r = 162.18	Z = 8
Orthorhombic, Pbca	Mo Kα radiation
a = 8.5386 (7) Å	µ = 0.09 mm⁻¹
b = 10.4949 (9) Å	T = 297 K
c = 18.8536 (16) Å	0.64 × 0.55 × 0.32 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	1663 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2001)	1278 reflections with I > 2σ(I)
T_min = 0.683, T_max = 1.000	R_int = 0.032
8807 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.037	0 restraints
wR(F²) = 0.116	H-atom parameters constrained
S = 1.02	Δρ_max = 0.20 e Å⁻³
1663 reflections	Δρ_min = −0.13 e Å⁻³
110 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	0.34168 (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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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···Cg1^iv	0.97	2.80	3.6430 (16)	146
C10—H10A···Cg1^v	0.96	2.82	3.6260 (16)	143

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

Experimental details

Crystal data
Chemical formula	C₁₀H₁₀O₂
M_r	162.18
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	297
a, b, c (Å)	8.5386 (7), 10.4949 (9), 18.8536 (16)
V (Å³)	1689.5 (2)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.64 × 0.55 × 0.32

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2001)
T_min, T_max	0.683, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	8807, 1663, 1278
R_int	0.032
(sin θ/λ)_max (Å⁻¹)	0.616

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.037, 0.116, 1.02
No. of reflections	1663
No. of parameters	110
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.20, −0.13

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

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···Cg1^iv	0.97	2.80	3.6430 (16)	146
C10—H10A···Cg1^v	0.96	2.82	3.6260 (16)	143

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

Acknowledgements

This work was supported by the National Science Council, Tung Hai University and Feng Chia University in Taiwan.

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Volume 68| Part 11| November 2012| Page o3063

doi:10.1107/S1600536812040743

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