1,1,3-Trimethyl-3-phenyl­indane

Men, J.; Yang, M.-J.; Jiang, Y.; Chen, H.; Gao, G.-W.

doi:10.1107/S1600536808009690

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 64| Part 5| May 2008| Page o847

doi:10.1107/S1600536808009690

Open

access

1,1,3-Trimethyl-3-phenylindane

Jian Men,^a Mei-Jia Yang,^a Yan Jiang,^a Hua Chen ^a and Guo-Wei Gao ^a ^*

^aCollege of Chemistry, Sichuan University, Chengdu 610064, People's Republic of China
^*Correspondence e-mail: gaosunday@yahoo.com.cn

(Received 17 March 2008; accepted 8 April 2008; online 16 April 2008)

In the title compound, C₁₈H₂₀, the five-membered ring of the indane fragment adopts an envelope conformation, with the flap atom deviating by 0.399 (3) Å from the plane of the remaining four atoms. The dihedral angle between the phenyl ring and the indane benzene ring is 79.58 (7)°.

Related literature

For related literature, see: Bateman & Gordon (1974 , 1976 ); Ghosh & Mittal (1996 ); Feger et al. (1989 ).

Experimental

Crystal data

C₁₈H₂₀
M_r = 236.34
Triclinic, $[P \overline 1]$
a = 8.192 (2) Å
b = 8.426 (3) Å
c = 11.113 (4) Å
α = 69.30 (3)°
β = 79.44 (5)°
γ = 80.37 (2)°
V = 701.0 (7) Å³
Z = 2
Mo Kα radiation
μ = 0.06 mm⁻¹
T = 291 (2) K
0.46 × 0.44 × 0.42 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: none
3682 measured reflections
2582 independent reflections
1770 reflections with I > 2σ(I)
R_int = 0.007
3 standard reflections every 200 reflections intensity decay: 0.7%

Refinement

R[F² > 2σ(F²)] = 0.040
wR(F²) = 0.117
S = 1.06
2582 reflections
170 parameters
H-atom parameters constrained
Δρ_max = 0.17 e Å⁻³
Δρ_min = −0.14 e Å⁻³

Data collection: DIFRAC (Gabe & White, 1993 ); cell refinement: DIFRAC; data reduction: NRCVAX (Gabe et al., 1989 ); 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: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808009690/gk2139sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808009690/gk2139Isup2.hkl

checkCIF report

Comment top

Polyimides are well known for possessing excellent thermal and oxidative stability, as well as excellent mechanical properties (Ghosh & Mittal, 1996; Feger et al., 1989). Furthermore, polyimides with phenylindane diamines and/or dianhydrides incorporated into the polyimide backbone have been found to be soluble in high concentration in polar organic solvents (Bateman & Gordon, 1974). Phenylindane diamines are prepared by a process comprising acid-catalyzed dimerization of α-methylstyrene and subsequent nitration and reduction of the 1,1,3-trimethyl-3-phenyl-2,3-dihydro-1H-indene (Bateman & Gordon, 1976).

The molecule of the title compound is shown in Fig. 1. Rings A (C1–C6) and B (C13–C18) are planar and form dihedral angle of 79.58 (7)°. The B ring forms dihedral angle of 25.38 (14)° with the plane defined by the indane Csp3 atoms C7, C9 and C10.

Related literature top

For related literature, see: Bateman & Gordon (1974, 1976); Ghosh & Mittal (1996); Feger et al. (1989).

Experimental top

α-Methylstyrene (32.0 g, 0.30 mol) was added to a 500 ml flask equipped with a condenser and a mechanical stirrer, followed by slow addition of a previously prepared mixture of H₂SO₄ (68 ml) and H₂O (130 ml). The reaction mixture was refluxed for 20 h. After it was cooled to room temperature, the lower acid phase was drawn off and discarded. The organic phase containing the phenylindane was washed with water several times. The product was recrystallized from methanol that afforded white crystals (24 g, yield 68%, m.p. 323–324 K).

Computing details top

Data collection: DIFRAC (Gabe & White, 1993); cell refinement: DIFRAC (Gabe & White, 1993); data reduction: NRCVAX (Gabe et al., 1989); 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: SHELXL97 (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of the title compound with displacement ellipsoids drawn at the 30% probability level.

1,1,3-Trimethyl-3-phenylindane top

Crystal data top

C₁₈H₂₀	Z = 2
M_r = 236.34	F(000) = 256
Triclinic, P1	D_x = 1.120 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.192 (2) Å	Cell parameters from 28 reflections
b = 8.426 (3) Å	θ = 4.4–7.7°
c = 11.113 (4) Å	µ = 0.06 mm⁻¹
α = 69.30 (3)°	T = 291 K
β = 79.44 (5)°	Block, colourless
γ = 80.37 (2)°	0.46 × 0.44 × 0.42 mm
V = 701.0 (7) Å³

Data collection top

Enraf–Nonius CAD-4 diffractometer	R_int = 0.007
Radiation source: fine-focus sealed tube	θ_max = 25.5°, θ_min = 2.6°
Graphite monochromator	h = −9→9
ω/2τ scans	k = −3→10
3682 measured reflections	l = −12→13
2582 independent reflections	3 standard reflections every 200 reflections
1770 reflections with I > 2σ(I)	intensity decay: 0.7%

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)] = 0.040	H-atom parameters constrained
wR(F²) = 0.117	w = 1/[σ²(F_o²) + (0.0549P)² + 0.0915P] where P = (F_o² + 2F_c²)/3
S = 1.06	(Δ/σ)_max < 0.001
2582 reflections	Δρ_max = 0.17 e Å⁻³
170 parameters	Δρ_min = −0.14 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.154 (10)

Crystal data top

C₁₈H₂₀	γ = 80.37 (2)°
M_r = 236.34	V = 701.0 (7) Å³
Triclinic, P1	Z = 2
a = 8.192 (2) Å	Mo Kα radiation
b = 8.426 (3) Å	µ = 0.06 mm⁻¹
c = 11.113 (4) Å	T = 291 K
α = 69.30 (3)°	0.46 × 0.44 × 0.42 mm
β = 79.44 (5)°

Data collection top

Enraf–Nonius CAD-4 diffractometer	R_int = 0.007
3682 measured reflections	3 standard reflections every 200 reflections
2582 independent reflections	intensity decay: 0.7%
1770 reflections with I > 2σ(I)

Refinement top

R[F² > 2σ(F²)] = 0.040	0 restraints
wR(F²) = 0.117	H-atom parameters constrained
S = 1.06	Δρ_max = 0.17 e Å⁻³
2582 reflections	Δρ_min = −0.14 e Å⁻³
170 parameters

Special details top

Experimental. ¹H NMR (400 MHz, CDCl₃): δ = 1.03, 1.35, 1.69 (s, 3H, –CH₃), 2.21 and 2.40 (d, 2H, –CH₂–), 7.11–7.29 (m, 9H, Ar—H).

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 > 2σ(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
C18	0.39195 (18)	0.00422 (18)	0.21135 (14)	0.0428 (4)
C6	0.20481 (17)	0.27044 (18)	0.22736 (14)	0.0436 (4)
C14	0.6116 (2)	−0.1842 (2)	0.32179 (15)	0.0527 (4)
H14	0.7136	−0.2011	0.3526	0.063*
C13	0.54458 (18)	−0.02135 (18)	0.25548 (14)	0.0421 (4)
C7	0.34020 (18)	0.19224 (19)	0.14280 (14)	0.0453 (4)
C17	0.3069 (2)	−0.1345 (2)	0.23220 (17)	0.0567 (4)
H17	0.2043	−0.1181	0.2025	0.068*
C10	0.61857 (19)	0.14541 (19)	0.22095 (15)	0.0478 (4)
C1	0.1330 (2)	0.4375 (2)	0.17672 (18)	0.0595 (5)
H1	0.1670	0.5006	0.0908	0.071*
C5	0.1502 (2)	0.1821 (2)	0.35573 (16)	0.0542 (4)
H5	0.1951	0.0697	0.3928	0.065*
C3	−0.0391 (2)	0.4221 (3)	0.3779 (2)	0.0665 (5)
H3	−0.1201	0.4724	0.4279	0.080*
C15	0.5266 (2)	−0.3214 (2)	0.34208 (17)	0.0606 (5)
H15	0.5716	−0.4313	0.3863	0.073*
C2	0.0126 (2)	0.5121 (2)	0.2504 (2)	0.0696 (5)
H2	−0.0339	0.6240	0.2137	0.083*
C4	0.0303 (2)	0.2575 (3)	0.43009 (18)	0.0653 (5)
H4	−0.0034	0.1957	0.5164	0.078*
C9	0.5091 (2)	0.2673 (2)	0.11982 (16)	0.0543 (4)
H9A	0.5650	0.2782	0.0329	0.065*
H9B	0.4892	0.3795	0.1289	0.065*
C16	0.3754 (2)	−0.2966 (2)	0.29712 (18)	0.0640 (5)
H16	0.3192	−0.3899	0.3107	0.077*
C8	0.2796 (2)	0.2204 (2)	0.01297 (16)	0.0664 (5)
H8A	0.3617	0.1654	−0.0374	0.100*
H8B	0.2635	0.3405	−0.0340	0.100*
H8C	0.1759	0.1728	0.0293	0.100*
C11	0.5994 (3)	0.1997 (2)	0.34135 (19)	0.0690 (5)
H11A	0.4832	0.2128	0.3749	0.104*
H11B	0.6446	0.3062	0.3180	0.104*
H11C	0.6585	0.1139	0.4065	0.104*
C12	0.8028 (2)	0.1333 (3)	0.1630 (2)	0.0723 (6)
H12A	0.8426	0.2429	0.1377	0.109*
H12B	0.8146	0.0980	0.0883	0.109*
H12C	0.8669	0.0513	0.2266	0.109*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C18	0.0409 (8)	0.0477 (9)	0.0410 (8)	−0.0052 (7)	−0.0006 (6)	−0.0185 (7)
C6	0.0386 (8)	0.0477 (9)	0.0461 (9)	−0.0021 (7)	−0.0125 (7)	−0.0155 (7)
C14	0.0555 (10)	0.0501 (10)	0.0506 (9)	0.0029 (8)	−0.0100 (8)	−0.0171 (8)
C13	0.0434 (8)	0.0441 (8)	0.0388 (8)	−0.0017 (6)	−0.0031 (6)	−0.0162 (7)
C7	0.0423 (8)	0.0506 (9)	0.0411 (8)	−0.0023 (7)	−0.0078 (6)	−0.0131 (7)
C17	0.0481 (9)	0.0637 (11)	0.0656 (11)	−0.0115 (8)	−0.0018 (8)	−0.0309 (9)
C10	0.0422 (8)	0.0472 (9)	0.0537 (9)	−0.0060 (7)	−0.0078 (7)	−0.0155 (7)
C1	0.0623 (11)	0.0537 (10)	0.0595 (11)	−0.0005 (8)	−0.0128 (9)	−0.0157 (8)
C5	0.0530 (10)	0.0568 (10)	0.0482 (9)	0.0022 (8)	−0.0064 (8)	−0.0158 (8)
C3	0.0483 (10)	0.0852 (14)	0.0811 (14)	0.0089 (9)	−0.0138 (9)	−0.0509 (12)
C15	0.0738 (12)	0.0422 (9)	0.0581 (10)	−0.0012 (8)	−0.0002 (9)	−0.0138 (8)
C2	0.0668 (12)	0.0601 (11)	0.0882 (15)	0.0127 (9)	−0.0238 (11)	−0.0348 (11)
C4	0.0590 (11)	0.0837 (14)	0.0536 (10)	−0.0014 (10)	−0.0020 (9)	−0.0289 (10)
C9	0.0491 (9)	0.0510 (9)	0.0525 (10)	−0.0069 (7)	−0.0026 (7)	−0.0063 (8)
C16	0.0715 (12)	0.0493 (10)	0.0735 (12)	−0.0191 (9)	0.0083 (10)	−0.0267 (9)
C8	0.0659 (12)	0.0851 (13)	0.0473 (10)	0.0056 (10)	−0.0148 (9)	−0.0236 (9)
C11	0.0802 (13)	0.0639 (11)	0.0758 (13)	−0.0119 (9)	−0.0212 (10)	−0.0317 (10)
C12	0.0464 (10)	0.0720 (12)	0.0943 (15)	−0.0103 (9)	−0.0070 (10)	−0.0219 (11)

Geometric parameters (Å, º) top

C18—C13	1.382 (2)	C5—H5	0.9300
C18—C17	1.388 (2)	C3—C4	1.368 (3)
C18—C7	1.520 (2)	C3—C2	1.375 (3)
C6—C5	1.384 (3)	C3—H3	0.9300
C6—C1	1.388 (2)	C15—C16	1.376 (3)
C6—C7	1.536 (2)	C15—H15	0.9300
C14—C15	1.379 (2)	C2—H2	0.9300
C14—C13	1.382 (2)	C4—H4	0.9300
C14—H14	0.9300	C9—H9A	0.9700
C13—C10	1.519 (2)	C9—H9B	0.9700
C7—C8	1.538 (2)	C16—H16	0.9300
C7—C9	1.558 (2)	C8—H8A	0.9600
C17—C16	1.377 (3)	C8—H8B	0.9600
C17—H17	0.9300	C8—H8C	0.9600
C10—C12	1.530 (2)	C11—H11A	0.9600
C10—C11	1.535 (3)	C11—H11B	0.9600
C10—C9	1.539 (2)	C11—H11C	0.9600
C1—C2	1.378 (3)	C12—H12A	0.9600
C1—H1	0.9300	C12—H12B	0.9600
C5—C4	1.385 (2)	C12—H12C	0.9600

C13—C18—C17	119.85 (15)	C16—C15—C14	120.29 (16)
C13—C18—C7	111.75 (13)	C16—C15—H15	119.9
C17—C18—C7	128.40 (14)	C14—C15—H15	119.9
C5—C6—C1	116.91 (16)	C3—C2—C1	120.35 (18)
C5—C6—C7	122.83 (14)	C3—C2—H2	119.8
C1—C6—C7	120.26 (15)	C1—C2—H2	119.8
C15—C14—C13	119.63 (16)	C3—C4—C5	120.67 (18)
C15—C14—H14	120.2	C3—C4—H4	119.7
C13—C14—H14	120.2	C5—C4—H4	119.7
C14—C13—C18	120.23 (15)	C10—C9—C7	108.20 (13)
C14—C13—C10	128.01 (14)	C10—C9—H9A	110.1
C18—C13—C10	111.76 (14)	C7—C9—H9A	110.1
C18—C7—C6	112.36 (13)	C10—C9—H9B	110.1
C18—C7—C8	111.23 (14)	C7—C9—H9B	110.1
C6—C7—C8	109.72 (13)	H9A—C9—H9B	108.4
C18—C7—C9	100.82 (13)	C15—C16—C17	120.42 (16)
C6—C7—C9	111.63 (13)	C15—C16—H16	119.8
C8—C7—C9	110.83 (14)	C17—C16—H16	119.8
C16—C17—C18	119.56 (16)	C7—C8—H8A	109.5
C16—C17—H17	120.2	C7—C8—H8B	109.5
C18—C17—H17	120.2	H8A—C8—H8B	109.5
C13—C10—C12	112.22 (14)	C7—C8—H8C	109.5
C13—C10—C11	110.21 (14)	H8A—C8—H8C	109.5
C12—C10—C11	109.67 (15)	H8B—C8—H8C	109.5
C13—C10—C9	101.46 (13)	C10—C11—H11A	109.5
C12—C10—C9	111.39 (15)	C10—C11—H11B	109.5
C11—C10—C9	111.70 (15)	H11A—C11—H11B	109.5
C2—C1—C6	121.72 (18)	C10—C11—H11C	109.5
C2—C1—H1	119.1	H11A—C11—H11C	109.5
C6—C1—H1	119.1	H11B—C11—H11C	109.5
C6—C5—C4	121.37 (17)	C10—C12—H12A	109.5
C6—C5—H5	119.3	C10—C12—H12B	109.5
C4—C5—H5	119.3	H12A—C12—H12B	109.5
C4—C3—C2	118.96 (18)	C10—C12—H12C	109.5
C4—C3—H3	120.5	H12A—C12—H12C	109.5
C2—C3—H3	120.5	H12B—C12—H12C	109.5

Experimental details

Crystal data
Chemical formula	C₁₈H₂₀
M_r	236.34
Crystal system, space group	Triclinic, P1
Temperature (K)	291
a, b, c (Å)	8.192 (2), 8.426 (3), 11.113 (4)
α, β, γ (°)	69.30 (3), 79.44 (5), 80.37 (2)
V (Å³)	701.0 (7)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.06
Crystal size (mm)	0.46 × 0.44 × 0.42

Data collection
Diffractometer	Enraf–Nonius CAD-4 diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	3682, 2582, 1770
R_int	0.007
(sin θ/λ)_max (Å⁻¹)	0.606

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.040, 0.117, 1.06
No. of reflections	2582
No. of parameters	170
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.17, −0.14

Computer programs: DIFRAC (Gabe & White, 1993), NRCVAX (Gabe et al., 1989), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997).

Acknowledgements

The authors are grateful to the National Undergraduates' Innovative Experiment Project of China for financial support, and thank Mr Zhi-Hua Mao of Sichuan University for the X-ray data collection.

References

Bateman, J. & Gordon, D. A. (1974). US Patent 3856752. Google Scholar
Bateman, J. & Gordon, D. A. (1976). US Patent 3983092. Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Feger, C., Khohasteh, M. M. & McGrath, J. E. (1989). Editors. Polyimides: Chemistry, Materials and Characterization. Amsterdam: Elsevier. Google Scholar
Gabe, E. J., Le Page, Y., Charland, J.-P., Lee, F. L. & White, P. S. (1989). J. Appl. Cryst. 22, 384–387. CrossRef CAS Web of Science IUCr Journals Google Scholar
Gabe, E. J. & White, P. S. (1993). Am. Crystallogr. Assoc. Pittsburgh Meet. Abstract PA104. Google Scholar
Ghosh, M. K. & Mittal, K. L. (1996). Polyimides: Fundamentals and Applications. New York: Dekker. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar