organic compounds
1,1,3-Trimethyl-3-phenylindane
aCollege of Chemistry, Sichuan University, Chengdu 610064, People's Republic of China
*Correspondence e-mail: gaosunday@yahoo.com.cn
In the title compound, C18H20, the five-membered ring of the indane fragment adopts an 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
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Data collection: DIFRAC (Gabe & White, 1993); cell 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
10.1107/S1600536808009690/gk2139sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536808009690/gk2139Isup2.hkl
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).
H atoms were positioned geometrically (C—H = 0.93–0.97 Å) and refined using a riding model, with Uiso(H) = 1.2Ueq (aromatic, methylene) or Uiso(H) = 1.5Ueq(methyl).
Data collection: DIFRAC (Gabe & White, 1993); cell
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).Fig. 1. The molecular structure of the title compound with displacement ellipsoids drawn at the 30% probability level. |
C18H20 | Z = 2 |
Mr = 236.34 | F(000) = 256 |
Triclinic, P1 | Dx = 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 |
Enraf–Nonius CAD-4 diffractometer | Rint = 0.007 |
Radiation source: fine-focus sealed tube | θmax = 25.5°, θmin = 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 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(Fo2) + (0.0549P)2 + 0.0915P] where P = (Fo2 + 2Fc2)/3 |
S = 1.06 | (Δ/σ)max < 0.001 |
2582 reflections | Δρmax = 0.17 e Å−3 |
170 parameters | Δρmin = −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) |
C18H20 | γ = 80.37 (2)° |
Mr = 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)° |
Enraf–Nonius CAD-4 diffractometer | Rint = 0.007 |
3682 measured reflections | 3 standard reflections every 200 reflections |
2582 independent reflections | intensity decay: 0.7% |
1770 reflections with I > 2σ(I) |
R[F2 > 2σ(F2)] = 0.040 | 0 restraints |
wR(F2) = 0.117 | H-atom parameters constrained |
S = 1.06 | Δρmax = 0.17 e Å−3 |
2582 reflections | Δρmin = −0.14 e Å−3 |
170 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
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* |
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) |
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 |
Mr | 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 |
Rint | 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 |
Δρmax, Δρmin (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
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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
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This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
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.