2-(4-Methoxy­phen­yl)-1H-indene

Liu, P.; Liu, Z.; Wang, X.-W.; Wang, W.

doi:10.1107/S1600536808019776

organic compounds

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ISSN: 2056-9890

Volume 64| Part 8| August 2008| Page o1406

doi:10.1107/S1600536808019776

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2-(4-Methoxyphenyl)-1H-indene

Pu Liu,^a ^* Zhen Liu,^a Xiao-Wei Wang ^a and Wei Wang ^a

^aChemical Engineering and Pharmaceutical College, Henan University of Science and Technology, Luoyang 471003, People's Republic of China
^*Correspondence e-mail: liudeng20022002@yahoo.com.cn

(Received 27 April 2008; accepted 28 June 2008; online 5 July 2008)

Excluding four H atoms, the molecule of the title compound, C₁₆H₁₄O, is almost planar, with an r.m.s. deviation of 0.0801 (2) Å. Due to p–π conjugation, the lengths of the two single bonds attached to the O atom are significantly different.

Related literature

For related literature, see: Rayabarapu et al. (2003 ); Senanayake et al. (1995 ).

Experimental

Crystal data

C₁₆H₁₄O
M_r = 222.27
Monoclinic, P 2₁ /c
a = 5.8347 (8) Å
b = 7.5584 (10) Å
c = 26.135 (4) Å
β = 92.772 (11)°
V = 1151.3 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 113 (2) K
0.34 × 0.32 × 0.12 mm

Data collection

Rigaku Saturn diffractometer
Absorption correction: multi-scan (CrystalClear; Molecular Structure Corporation & Rigaku, 1999 ) T_min = 0.974, T_max = 0.991
10940 measured reflections
2724 independent reflections
2360 reflections with I > 2σ(I)
R_int = 0.038

Refinement

R[F² > 2σ(F²)] = 0.051
wR(F²) = 0.135
S = 1.10
2724 reflections
155 parameters
H-atom parameters constrained
Δρ_max = 0.32 e Å⁻³
Δρ_min = −0.39 e Å⁻³

Table 1
Selected geometric parameters (Å, °)

O1—C1	1.3724 (16)
O1—C16	1.4301 (19)

Data collection: CrystalClear (Molecular Structure Corporation & Rigaku, 1999); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808019776/wk2085sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808019776/wk2085Isup2.hkl

checkCIF report

Comment top

Indene ring frameworks are present in a large number of biologically active compounds, and their metallocene complexes are able to catalyze olefin polymerization (Senanayake et al., 1995; Rayabarapu et al., 2003). Some derivatives have shown analgesic and myorelaxation activity, and others are used as valuable intermediates for the synthesis of indenyl chrysanthemates that possess insecticidal properties. So in the recent three decades, many chemists have been attracted by the synthesis of indenes. In this context, we report the synthesis and crystal structure of the title compound, (I), namely 2-(4-methoxyphenyl)-1H-indene.

The title compound was obtained as colourless plate-like crystals in the monoclinic space group P 1 21/c 1. A view of the molecular structure of (I) with the numbering scheme is shown in Fig. 1. The whole molecular structure is almost planar with an r.m.s. deviation of 0.0801 (2) Å. Due to the p–π conjugation of atom O1 and benzene ring, the single-bond distance of the O1—C1 [1.3724 (16) Å] is significantly shorter than that of O1—C16 [1.4301 (19) Å].

Related literature top

For related literature, see: Rayabarapu et al. (2003); Senanayake et al. (1995).

Experimental top

o-Bromobenzyl zinc bromide (3.5 mmol, 3.5 equiv) in 3.5 ml CH₂Cl₂ was added to a degassed refluxing CH₂Cl₂ solution (8 ml) of 1-ethynyl-4-methoxybenzene (1.0 mmol, 1.0 equiv) and Ni(PPh₃)₂I₂ (0.1 mmol, 0.1 equiv). After being stirred at 313 K for 6 h, the solution was cooled to room temperature. The resultant solution was diluted with 50 ml ethyl acetate. The organic layer was washed with 10 ml aqueous HCl solution, saturated NaCl. The aqueous layer was back-extracted with Ethyl acetate. The combined organic layer was dried over anhydrous Na₂SO₄. After filtration, the solvent was removed under reduced pressure and the residue was purified via flash chromatography (SiO₂) to afford the compound. Single crystal suitale for X-ray analysis were obtained by slow evaporation at 298 K of a CH₂Cl₂ solution.

Computing details top

Data collection: CrystalClear (Molecular Structure Corporation & Rigaku, 1999); cell refinement: CrystalClear (Molecular Structure Corporation & Rigaku, 1999); data reduction: CrystalClear (Molecular Structure Corporation & Rigaku, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

Fig. 1. View of the molecule of (I) showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 35% probability level.

2-(4-Methoxyphenyl)-1H-indene top

Crystal data top

C₁₆H₁₄O	F(000) = 472
M_r = 222.27	D_x = 1.282 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71070 Å
Hall symbol: -P 2ybc	Cell parameters from 2782 reflections
a = 5.8347 (8) Å	θ = 2.8–27.9°
b = 7.5584 (10) Å	µ = 0.08 mm⁻¹
c = 26.135 (4) Å	T = 113 K
β = 92.772 (11)°	Plate, colourless
V = 1151.3 (3) Å³	0.34 × 0.32 × 0.12 mm
Z = 4

Data collection top

Rigaku Saturn diffractometer	2724 independent reflections
Radiation source: rotating anode	2360 reflections with I > 2σ(I)
Confocal monochromator	R_int = 0.038
Detector resolution: 7.31 pixels mm^-1	θ_max = 27.9°, θ_min = 2.8°
ω scans	h = −7→7
Absorption correction: multi-scan (CrystalClear; Molecular Structure Corporation & Rigaku, 1999)	k = −9→9
T_min = 0.974, T_max = 0.991	l = −34→34
10940 measured reflections

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)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.135	H-atom parameters constrained
S = 1.10	w = 1/[σ²(F_o²) + (0.0654P)² + 0.4321P] where P = (F_o² + 2F_c²)/3
2724 reflections	(Δ/σ)_max < 0.001
155 parameters	Δρ_max = 0.32 e Å⁻³
0 restraints	Δρ_min = −0.39 e Å⁻³

Crystal data top

C₁₆H₁₄O	V = 1151.3 (3) Å³
M_r = 222.27	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 5.8347 (8) Å	µ = 0.08 mm⁻¹
b = 7.5584 (10) Å	T = 113 K
c = 26.135 (4) Å	0.34 × 0.32 × 0.12 mm
β = 92.772 (11)°

Data collection top

Rigaku Saturn diffractometer	2724 independent reflections
Absorption correction: multi-scan (CrystalClear; Molecular Structure Corporation & Rigaku, 1999)	2360 reflections with I > 2σ(I)
T_min = 0.974, T_max = 0.991	R_int = 0.038
10940 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.051	0 restraints
wR(F²) = 0.135	H-atom parameters constrained
S = 1.10	Δρ_max = 0.32 e Å⁻³
2724 reflections	Δρ_min = −0.39 e Å⁻³
155 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	0.06468 (18)	0.38400 (14)	0.43568 (4)	0.0246 (3)
C1	0.0999 (2)	0.37824 (18)	0.38417 (5)	0.0196 (3)
C2	−0.0458 (2)	0.29441 (18)	0.34780 (5)	0.0209 (3)
H2	−0.1824	0.2384	0.3578	0.025*
C3	0.0118 (2)	0.29399 (18)	0.29665 (5)	0.0205 (3)
H3	−0.0875	0.2366	0.2720	0.025*
C4	0.2110 (2)	0.37525 (17)	0.28040 (5)	0.0188 (3)
C5	0.3523 (2)	0.46050 (18)	0.31800 (5)	0.0207 (3)
H5	0.4884	0.5177	0.3082	0.025*
C6	0.2972 (2)	0.46277 (18)	0.36889 (5)	0.0217 (3)
H6	0.3944	0.5223	0.3935	0.026*
C7	0.2705 (2)	0.37168 (17)	0.22661 (5)	0.0191 (3)
C8	0.4701 (2)	0.44705 (18)	0.20655 (5)	0.0203 (3)
H8	0.5885	0.5082	0.2255	0.024*
C9	0.4594 (2)	0.41280 (18)	0.15079 (5)	0.0193 (3)
C10	0.6102 (3)	0.45594 (19)	0.11311 (5)	0.0234 (3)
H10	0.7468	0.5203	0.1215	0.028*
C11	0.5577 (3)	0.40313 (19)	0.06279 (6)	0.0251 (3)
H11	0.6602	0.4309	0.0368	0.030*
C12	0.3566 (3)	0.31006 (19)	0.05014 (5)	0.0246 (3)
H12	0.3239	0.2747	0.0157	0.030*
C13	0.2030 (3)	0.26833 (18)	0.08766 (5)	0.0220 (3)
H13	0.0648	0.2064	0.0790	0.026*
C14	0.2559 (2)	0.31909 (17)	0.13805 (5)	0.0188 (3)
C15	0.1310 (2)	0.29032 (18)	0.18543 (5)	0.0197 (3)
H15A	−0.0226	0.3461	0.1824	0.024*
H15B	0.1118	0.1623	0.1919	0.024*
C16	−0.1393 (3)	0.3029 (2)	0.45282 (6)	0.0311 (4)
H16A	−0.1495	0.3227	0.4897	0.047*
H16B	−0.1347	0.1755	0.4460	0.047*
H16C	−0.2736	0.3548	0.4345	0.047*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0271 (6)	0.0282 (6)	0.0184 (5)	−0.0015 (4)	0.0008 (4)	0.0018 (4)
C1	0.0221 (7)	0.0180 (6)	0.0187 (6)	0.0040 (5)	−0.0003 (5)	0.0017 (5)
C2	0.0195 (7)	0.0196 (7)	0.0237 (7)	−0.0020 (5)	0.0006 (5)	0.0014 (5)
C3	0.0205 (7)	0.0188 (6)	0.0219 (7)	−0.0012 (5)	−0.0019 (5)	−0.0009 (5)
C4	0.0197 (7)	0.0141 (6)	0.0224 (7)	0.0037 (5)	0.0004 (5)	0.0003 (5)
C5	0.0179 (7)	0.0195 (7)	0.0247 (7)	−0.0006 (5)	0.0011 (5)	−0.0011 (5)
C6	0.0205 (7)	0.0204 (7)	0.0240 (7)	0.0004 (5)	−0.0025 (5)	−0.0020 (5)
C7	0.0216 (7)	0.0139 (6)	0.0220 (7)	0.0030 (5)	0.0012 (5)	−0.0006 (5)
C8	0.0181 (7)	0.0212 (7)	0.0215 (7)	−0.0014 (5)	−0.0001 (5)	−0.0021 (5)
C9	0.0193 (7)	0.0158 (6)	0.0225 (7)	0.0011 (5)	−0.0001 (5)	−0.0001 (5)
C10	0.0229 (7)	0.0209 (7)	0.0267 (7)	−0.0024 (6)	0.0026 (6)	0.0015 (5)
C11	0.0280 (8)	0.0241 (7)	0.0235 (7)	0.0019 (6)	0.0060 (6)	0.0053 (6)
C12	0.0311 (8)	0.0230 (7)	0.0198 (7)	0.0021 (6)	0.0006 (6)	0.0011 (5)
C13	0.0242 (8)	0.0200 (7)	0.0216 (7)	−0.0013 (6)	−0.0018 (5)	0.0005 (5)
C14	0.0191 (7)	0.0157 (6)	0.0216 (7)	0.0016 (5)	0.0002 (5)	0.0011 (5)
C15	0.0192 (7)	0.0185 (6)	0.0211 (6)	0.0008 (5)	−0.0008 (5)	−0.0004 (5)
C16	0.0332 (9)	0.0371 (9)	0.0234 (7)	−0.0048 (7)	0.0043 (6)	0.0049 (6)

Geometric parameters (Å, º) top

O1—C1	1.3724 (16)	C9—C10	1.391 (2)
O1—C16	1.4301 (19)	C9—C14	1.409 (2)
C1—C6	1.392 (2)	C10—C11	1.394 (2)
C1—C2	1.3963 (19)	C10—H10	0.9500
C2—C3	1.394 (2)	C11—C12	1.394 (2)
C2—H2	0.9500	C11—H11	0.9500
C3—C4	1.399 (2)	C12—C13	1.397 (2)
C3—H3	0.9500	C12—H12	0.9500
C4—C5	1.4078 (19)	C13—C14	1.3919 (19)
C4—C7	1.4645 (19)	C13—H13	0.9500
C5—C6	1.384 (2)	C14—C15	1.4829 (19)
C5—H5	0.9500	C15—H15A	0.9900
C6—H6	0.9500	C15—H15B	0.9900
C7—C8	1.419 (2)	C16—H16A	0.9800
C7—C15	1.4542 (19)	C16—H16B	0.9800
C8—C9	1.4785 (19)	C16—H16C	0.9800
C8—H8	0.9500

C1—O1—C16	117.40 (12)	C9—C10—C11	118.88 (14)
O1—C1—C6	115.60 (12)	C9—C10—H10	120.6
O1—C1—C2	124.55 (13)	C11—C10—H10	120.6
C6—C1—C2	119.85 (13)	C12—C11—C10	120.83 (14)
C3—C2—C1	119.13 (13)	C12—C11—H11	119.6
C3—C2—H2	120.4	C10—C11—H11	119.6
C1—C2—H2	120.4	C11—C12—C13	120.59 (13)
C2—C3—C4	122.18 (13)	C11—C12—H12	119.7
C2—C3—H3	118.9	C13—C12—H12	119.7
C4—C3—H3	118.9	C14—C13—C12	118.78 (14)
C3—C4—C5	117.14 (13)	C14—C13—H13	120.6
C3—C4—C7	121.50 (12)	C12—C13—H13	120.6
C5—C4—C7	121.36 (13)	C13—C14—C9	120.54 (13)
C6—C5—C4	121.43 (13)	C13—C14—C15	130.85 (13)
C6—C5—H5	119.3	C9—C14—C15	108.60 (12)
C4—C5—H5	119.3	C7—C15—C14	106.02 (12)
C5—C6—C1	120.26 (13)	C7—C15—H15A	110.5
C5—C6—H6	119.9	C14—C15—H15A	110.5
C1—C6—H6	119.9	C7—C15—H15B	110.5
C8—C7—C15	109.64 (12)	C14—C15—H15B	110.5
C8—C7—C4	125.75 (12)	H15A—C15—H15B	108.7
C15—C7—C4	124.61 (13)	O1—C16—H16A	109.5
C7—C8—C9	107.34 (12)	O1—C16—H16B	109.5
C7—C8—H8	126.3	H16A—C16—H16B	109.5
C9—C8—H8	126.3	O1—C16—H16C	109.5
C10—C9—C14	120.36 (13)	H16A—C16—H16C	109.5
C10—C9—C8	131.24 (13)	H16B—C16—H16C	109.5
C14—C9—C8	108.40 (12)

C16—O1—C1—C6	178.34 (12)	C7—C8—C9—C10	−179.34 (14)
C16—O1—C1—C2	−2.0 (2)	C7—C8—C9—C14	0.24 (15)
O1—C1—C2—C3	−178.41 (13)	C14—C9—C10—C11	−0.7 (2)
C6—C1—C2—C3	1.3 (2)	C8—C9—C10—C11	178.81 (14)
C1—C2—C3—C4	−0.1 (2)	C9—C10—C11—C12	0.6 (2)
C2—C3—C4—C5	−0.7 (2)	C10—C11—C12—C13	0.3 (2)
C2—C3—C4—C7	179.21 (13)	C11—C12—C13—C14	−0.9 (2)
C3—C4—C5—C6	0.4 (2)	C12—C13—C14—C9	0.8 (2)
C7—C4—C5—C6	−179.47 (13)	C12—C13—C14—C15	−178.47 (14)
C4—C5—C6—C1	0.7 (2)	C10—C9—C14—C13	0.0 (2)
O1—C1—C6—C5	178.17 (12)	C8—C9—C14—C13	−179.60 (12)
C2—C1—C6—C5	−1.5 (2)	C10—C9—C14—C15	179.45 (12)
C3—C4—C7—C8	−178.77 (13)	C8—C9—C14—C15	−0.18 (15)
C5—C4—C7—C8	1.1 (2)	C8—C7—C15—C14	0.09 (15)
C3—C4—C7—C15	1.7 (2)	C4—C7—C15—C14	179.70 (12)
C5—C4—C7—C15	−178.42 (13)	C13—C14—C15—C7	179.39 (14)
C15—C7—C8—C9	−0.20 (15)	C9—C14—C15—C7	0.06 (15)
C4—C7—C8—C9	−179.80 (12)

Experimental details

Crystal data
Chemical formula	C₁₆H₁₄O
M_r	222.27
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	113
a, b, c (Å)	5.8347 (8), 7.5584 (10), 26.135 (4)
β (°)	92.772 (11)
V (Å³)	1151.3 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.34 × 0.32 × 0.12

Data collection
Diffractometer	Rigaku Saturn diffractometer
Absorption correction	Multi-scan (CrystalClear; Molecular Structure Corporation & Rigaku, 1999)
T_min, T_max	0.974, 0.991
No. of measured, independent and observed [I > 2σ(I)] reflections	10940, 2724, 2360
R_int	0.038
(sin θ/λ)_max (Å⁻¹)	0.658

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.051, 0.135, 1.10
No. of reflections	2724
No. of parameters	155
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.32, −0.39

Computer programs: CrystalClear (Molecular Structure Corporation & Rigaku, 1999), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Selected geometric parameters (Å, º) top

O1—C1	1.3724 (16)	O1—C16	1.4301 (19)

C8—C7—C15	109.64 (12)	C13—C14—C15	130.85 (13)
C8—C7—C4	125.75 (12)	C9—C14—C15	108.60 (12)

Acknowledgements

The project was supported by the Fund for Doctorates of Henan University of Science and Technology.

References

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