Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536801021080/bt6094sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536801021080/bt6094Isup2.hkl |
CCDC reference: 180536
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.006 Å
- R factor = 0.036
- wR factor = 0.076
- Data-to-parameter ratio = 7.9
checkCIF results
No syntax errors found ADDSYM reports no extra symmetry General Notes
REFLT_03 From the CIF: _diffrn_reflns_theta_max 25.34 From the CIF: _reflns_number_total 1285 Count of symmetry unique reflns 1329 Completeness (_total/calc) 96.69% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 0 Fraction of Friedel pairs measured 0.000 Are heavy atom types Z>Si present no Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF.
The general procedure was the one described by Dansi & Pasini (1951). 10 g of indene (>99.0% purity) and 40 ml 48% H2SO4, as a two-phase mixture, were refluxed (oil-bath temperature 398–403 K) with vigorous stirring for 8 h. After cooling to room temperature, 100 ml cyclohexane were added. The reaction mixture was neutralized with NaHCO3 (5%), washed with water and dried over Na2SO4. After evaporating the cyclohexane, 8.7 g of yellow viscous oil were obtained. It contained more than 85% of (I), which was isolated by crystallization from propan-2-ol.
H atoms were placed in calculated positions with Uiso constrained to be 1.2 times Ueq of the carrier atom. Friedel opposites were merged and no attempts were made to refine the absolute configuration.
Data collection: COLLECT (Nonius, 1998); cell refinement: DENZO and SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO and SCALEPACK; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL-Plus (Sheldrick, 1991); software used to prepare material for publication: SHELXL97, PARST95 (Nardelli, 1995) and PLATON (Spek, 2001).
C18H16 | Dx = 1.173 Mg m−3 |
Mr = 232.31 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, Fdd2 | Cell parameters from 10913 reflections |
a = 20.2837 (8) Å | θ = 3.5–25.3° |
b = 42.098 (2) Å | µ = 0.07 mm−1 |
c = 6.1644 (2) Å | T = 293 K |
V = 5263.8 (4) Å3 | Needle, colourless |
Z = 16 | 0.50 × 0.05 × 0.02 mm |
F(000) = 1984 |
Nonius KappaCCD diffractometer | 565 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.041 |
Graphite monochromator | θmax = 25.3°, θmin = 3.5° |
Detector resolution: 10 vertical, 18 horizontal pixels mm-1 | h = −23→23 |
319 frames via ω–rotation (Δω=1°) with 3 sets at different κ–angles and two times 150 s per frame scans | k = −50→50 |
10913 measured reflections | l = −7→7 |
1285 independent reflections |
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)] = 0.036 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.076 | H-atom parameters constrained |
S = 0.82 | w = 1/[σ2(Fo2) + (0.0275P)2] where P = (Fo2 + 2Fc2)/3 |
1285 reflections | (Δ/σ)max < 0.001 |
163 parameters | Δρmax = 0.10 e Å−3 |
1 restraint | Δρmin = −0.10 e Å−3 |
C18H16 | V = 5263.8 (4) Å3 |
Mr = 232.31 | Z = 16 |
Orthorhombic, Fdd2 | Mo Kα radiation |
a = 20.2837 (8) Å | µ = 0.07 mm−1 |
b = 42.098 (2) Å | T = 293 K |
c = 6.1644 (2) Å | 0.50 × 0.05 × 0.02 mm |
Nonius KappaCCD diffractometer | 565 reflections with I > 2σ(I) |
10913 measured reflections | Rint = 0.041 |
1285 independent reflections |
R[F2 > 2σ(F2)] = 0.036 | 1 restraint |
wR(F2) = 0.076 | H-atom parameters constrained |
S = 0.82 | Δρmax = 0.10 e Å−3 |
1285 reflections | Δρmin = −0.10 e Å−3 |
163 parameters |
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 | ||
C1 | 0.3605 (2) | 0.13592 (11) | −0.2578 (7) | 0.1197 (15) | |
H1A | 0.3488 | 0.1336 | −0.4096 | 0.144* | |
H1B | 0.4039 | 0.1455 | −0.2482 | 0.144* | |
C2 | 0.35917 (18) | 0.10474 (10) | −0.1460 (7) | 0.1097 (14) | |
H2A | 0.4038 | 0.0973 | −0.1208 | 0.132* | |
H2B | 0.3363 | 0.0892 | −0.2343 | 0.132* | |
C3 | 0.32261 (16) | 0.10933 (9) | 0.0740 (6) | 0.0755 (10) | |
H3A | 0.3555 | 0.1111 | 0.1898 | 0.091* | |
C4 | 0.29031 (17) | 0.14105 (9) | 0.0450 (6) | 0.0687 (10) | |
C5 | 0.24549 (19) | 0.15543 (10) | 0.1801 (7) | 0.0983 (13) | |
H5A | 0.2319 | 0.1453 | 0.3066 | 0.118* | |
C6 | 0.2208 (2) | 0.18492 (13) | 0.1270 (11) | 0.1176 (18) | |
H6A | 0.1910 | 0.1949 | 0.2191 | 0.141* | |
C7 | 0.2401 (3) | 0.19964 (11) | −0.0613 (14) | 0.129 (2) | |
H7A | 0.2229 | 0.2193 | −0.0995 | 0.155* | |
C8 | 0.2850 (3) | 0.18486 (13) | −0.1912 (9) | 0.1163 (17) | |
H8A | 0.2987 | 0.1949 | −0.3179 | 0.140* | |
C9 | 0.31012 (19) | 0.15584 (11) | −0.1401 (7) | 0.0806 (11) | |
C11 | 0.21865 (17) | 0.07384 (8) | −0.0097 (5) | 0.0766 (11) | |
H11A | 0.2331 | 0.0671 | −0.1524 | 0.092* | |
H11B | 0.1882 | 0.0914 | −0.0258 | 0.092* | |
C12 | 0.27638 (16) | 0.08309 (8) | 0.1289 (6) | 0.0667 (10) | |
C13 | 0.27698 (17) | 0.06421 (8) | 0.3037 (6) | 0.0717 (10) | |
H13A | 0.3082 | 0.0654 | 0.4140 | 0.086* | |
C14 | 0.22312 (18) | 0.04180 (8) | 0.2995 (6) | 0.0642 (9) | |
C15 | 0.2060 (2) | 0.01784 (10) | 0.4429 (6) | 0.0830 (11) | |
H15A | 0.2299 | 0.0146 | 0.5697 | 0.100* | |
C16 | 0.1529 (3) | −0.00105 (10) | 0.3929 (8) | 0.1007 (15) | |
H16A | 0.1413 | −0.0175 | 0.4864 | 0.121* | |
C17 | 0.1168 (2) | 0.00378 (11) | 0.2090 (11) | 0.1064 (15) | |
H17A | 0.0808 | −0.0092 | 0.1792 | 0.128* | |
C18 | 0.1334 (2) | 0.02803 (10) | 0.0660 (7) | 0.0911 (12) | |
H18 | 0.1086 | 0.0315 | −0.0586 | 0.109* | |
C19 | 0.18719 (19) | 0.04683 (8) | 0.1118 (6) | 0.0712 (10) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.161 (4) | 0.116 (4) | 0.082 (3) | 0.001 (3) | 0.036 (3) | 0.001 (3) |
C2 | 0.114 (3) | 0.099 (3) | 0.117 (4) | 0.003 (3) | 0.053 (3) | −0.010 (3) |
C3 | 0.077 (3) | 0.070 (3) | 0.079 (2) | −0.004 (2) | 0.005 (2) | −0.002 (2) |
C4 | 0.068 (2) | 0.064 (3) | 0.074 (3) | −0.010 (2) | 0.011 (2) | −0.003 (3) |
C5 | 0.094 (3) | 0.078 (3) | 0.122 (4) | −0.007 (3) | 0.037 (3) | −0.011 (3) |
C6 | 0.082 (3) | 0.067 (4) | 0.203 (6) | 0.001 (3) | 0.008 (4) | −0.034 (4) |
C7 | 0.105 (4) | 0.063 (4) | 0.219 (7) | −0.003 (3) | −0.068 (5) | 0.012 (5) |
C8 | 0.129 (4) | 0.099 (4) | 0.121 (4) | −0.015 (3) | −0.026 (4) | 0.023 (4) |
C9 | 0.093 (3) | 0.069 (3) | 0.080 (3) | 0.000 (2) | −0.006 (2) | 0.006 (3) |
C11 | 0.092 (3) | 0.072 (3) | 0.066 (3) | 0.011 (2) | −0.005 (2) | 0.000 (2) |
C12 | 0.067 (2) | 0.067 (2) | 0.067 (3) | 0.006 (2) | −0.004 (2) | −0.007 (2) |
C13 | 0.079 (3) | 0.073 (3) | 0.064 (2) | 0.010 (2) | −0.009 (2) | −0.003 (3) |
C14 | 0.078 (2) | 0.055 (3) | 0.059 (2) | 0.009 (2) | −0.001 (2) | 0.001 (2) |
C15 | 0.097 (3) | 0.070 (3) | 0.082 (3) | 0.011 (2) | 0.000 (3) | 0.003 (3) |
C16 | 0.110 (4) | 0.069 (3) | 0.123 (4) | −0.002 (3) | 0.026 (4) | 0.004 (3) |
C17 | 0.092 (3) | 0.076 (4) | 0.150 (5) | −0.013 (3) | 0.006 (4) | −0.025 (3) |
C18 | 0.083 (3) | 0.084 (3) | 0.106 (3) | 0.005 (2) | −0.019 (2) | −0.017 (3) |
C19 | 0.077 (3) | 0.065 (3) | 0.071 (3) | 0.003 (2) | −0.004 (2) | −0.010 (2) |
C1—C2 | 1.483 (5) | C8—H8A | 0.9300 |
C1—C9 | 1.507 (5) | C11—C12 | 1.501 (4) |
C1—H1A | 0.9700 | C11—C19 | 1.503 (4) |
C1—H1B | 0.9700 | C11—H11A | 0.9700 |
C2—C3 | 1.558 (5) | C11—H11B | 0.9700 |
C2—H2A | 0.9700 | C12—C13 | 1.339 (4) |
C2—H2B | 0.9700 | C13—C14 | 1.444 (4) |
C3—C12 | 1.488 (4) | C13—H13A | 0.9300 |
C3—C4 | 1.498 (4) | C14—C19 | 1.384 (4) |
C3—H3A | 0.9800 | C14—C15 | 1.385 (4) |
C4—C9 | 1.361 (4) | C15—C16 | 1.374 (5) |
C4—C5 | 1.374 (4) | C15—H15A | 0.9300 |
C5—C6 | 1.378 (5) | C16—C17 | 1.365 (5) |
C5—H5A | 0.9300 | C16—H16A | 0.9300 |
C6—C7 | 1.373 (7) | C17—C18 | 1.390 (6) |
C6—H6A | 0.9300 | C17—H17A | 0.9300 |
C7—C8 | 1.362 (7) | C18—C19 | 1.378 (5) |
C7—H7A | 0.9300 | C18—H18 | 0.9300 |
C8—C9 | 1.361 (5) | ||
C2—C1—C9 | 104.9 (3) | C4—C9—C8 | 119.6 (4) |
C2—C1—H1A | 110.8 | C4—C9—C1 | 110.4 (4) |
C9—C1—H1A | 110.8 | C8—C9—C1 | 129.9 (5) |
C2—C1—H1B | 110.8 | C12—C11—C19 | 104.1 (3) |
C9—C1—H1B | 110.8 | C12—C11—H11A | 110.9 |
H1A—C1—H1B | 108.8 | C19—C11—H11A | 110.9 |
C1—C2—C3 | 107.7 (3) | C12—C11—H11B | 110.9 |
C1—C2—H2A | 110.2 | C19—C11—H11B | 110.9 |
C3—C2—H2A | 110.2 | H11A—C11—H11B | 109.0 |
C1—C2—H2B | 110.2 | C13—C12—C3 | 128.2 (3) |
C3—C2—H2B | 110.2 | C13—C12—C11 | 108.1 (3) |
H2A—C2—H2B | 108.5 | C3—C12—C11 | 123.7 (3) |
C12—C3—C4 | 114.4 (3) | C12—C13—C14 | 111.5 (3) |
C12—C3—C2 | 113.9 (3) | C12—C13—H13A | 124.2 |
C4—C3—C2 | 102.4 (3) | C14—C13—H13A | 124.2 |
C12—C3—H3A | 108.6 | C19—C14—C15 | 120.9 (4) |
C4—C3—H3A | 108.6 | C19—C14—C13 | 108.3 (3) |
C2—C3—H3A | 108.6 | C15—C14—C13 | 130.8 (4) |
C9—C4—C5 | 120.1 (4) | C16—C15—C14 | 118.3 (4) |
C9—C4—C3 | 112.3 (3) | C16—C15—H15A | 120.8 |
C5—C4—C3 | 127.6 (4) | C14—C15—H15A | 120.8 |
C4—C5—C6 | 119.6 (4) | C17—C16—C15 | 121.4 (4) |
C4—C5—H5A | 120.2 | C17—C16—H16A | 119.3 |
C6—C5—H5A | 120.2 | C15—C16—H16A | 119.3 |
C7—C6—C5 | 120.3 (5) | C16—C17—C18 | 120.4 (4) |
C7—C6—H6A | 119.9 | C16—C17—H17A | 119.8 |
C5—C6—H6A | 119.9 | C18—C17—H17A | 119.8 |
C8—C7—C6 | 118.8 (5) | C19—C18—C17 | 119.0 (4) |
C8—C7—H7A | 120.6 | C19—C18—H18 | 120.5 |
C6—C7—H7A | 120.6 | C17—C18—H18 | 120.5 |
C7—C8—C9 | 121.6 (5) | C18—C19—C14 | 120.0 (4) |
C7—C8—H8A | 119.2 | C18—C19—C11 | 132.0 (4) |
C9—C8—H8A | 119.2 | C14—C19—C11 | 108.0 (3) |
C9—C1—C2—C3 | −15.3 (4) | C4—C3—C12—C11 | 57.5 (5) |
C1—C2—C3—C12 | 138.4 (4) | C2—C3—C12—C11 | −59.9 (4) |
C1—C2—C3—C4 | 14.3 (4) | C19—C11—C12—C13 | −0.4 (3) |
C12—C3—C4—C9 | −131.6 (3) | C19—C11—C12—C3 | −179.6 (3) |
C2—C3—C4—C9 | −7.8 (4) | C3—C12—C13—C14 | 179.2 (3) |
C12—C3—C4—C5 | 48.3 (5) | C11—C12—C13—C14 | 0.1 (4) |
C2—C3—C4—C5 | 172.1 (3) | C12—C13—C14—C19 | 0.3 (4) |
C9—C4—C5—C6 | −0.1 (5) | C12—C13—C14—C15 | 178.5 (3) |
C3—C4—C5—C6 | 180.0 (4) | C19—C14—C15—C16 | 0.7 (5) |
C4—C5—C6—C7 | 1.0 (7) | C13—C14—C15—C16 | −177.3 (4) |
C5—C6—C7—C8 | −1.4 (7) | C14—C15—C16—C17 | −1.1 (6) |
C6—C7—C8—C9 | 1.0 (8) | C15—C16—C17—C18 | 0.4 (6) |
C5—C4—C9—C8 | −0.4 (5) | C16—C17—C18—C19 | 0.7 (6) |
C3—C4—C9—C8 | 179.6 (3) | C17—C18—C19—C14 | −1.1 (5) |
C5—C4—C9—C1 | 178.5 (3) | C17—C18—C19—C11 | 178.1 (3) |
C3—C4—C9—C1 | −1.5 (4) | C15—C14—C19—C18 | 0.4 (5) |
C7—C8—C9—C4 | 0.0 (6) | C13—C14—C19—C18 | 178.8 (3) |
C7—C8—C9—C1 | −178.8 (4) | C15—C14—C19—C11 | −178.9 (3) |
C2—C1—C9—C4 | 10.7 (4) | C13—C14—C19—C11 | −0.6 (3) |
C2—C1—C9—C8 | −170.5 (4) | C12—C11—C19—C18 | −178.7 (3) |
C4—C3—C12—C13 | −121.5 (4) | C12—C11—C19—C14 | 0.6 (3) |
C2—C3—C12—C13 | 121.2 (4) |
Experimental details
Crystal data | |
Chemical formula | C18H16 |
Mr | 232.31 |
Crystal system, space group | Orthorhombic, Fdd2 |
Temperature (K) | 293 |
a, b, c (Å) | 20.2837 (8), 42.098 (2), 6.1644 (2) |
V (Å3) | 5263.8 (4) |
Z | 16 |
Radiation type | Mo Kα |
µ (mm−1) | 0.07 |
Crystal size (mm) | 0.50 × 0.05 × 0.02 |
Data collection | |
Diffractometer | Nonius KappaCCD diffractometer |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 10913, 1285, 565 |
Rint | 0.041 |
(sin θ/λ)max (Å−1) | 0.602 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.036, 0.076, 0.82 |
No. of reflections | 1285 |
No. of parameters | 163 |
No. of restraints | 1 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.10, −0.10 |
Computer programs: COLLECT (Nonius, 1998), DENZO and SCALEPACK (Otwinowski & Minor, 1997), DENZO and SCALEPACK, SHELXS97 (Sheldrick, 1990), SHELXL97 (Sheldrick, 1997), SHELXTL-Plus (Sheldrick, 1991), SHELXL97, PARST95 (Nardelli, 1995) and PLATON (Spek, 2001).
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The title compound, (I), represents the most stable dimer of indene obtained by the cationic dimerization through the reaction of the 2,3-dihydro-1H-inden-1-yl carbenium ion with 1H-indene at position 2. Compound (I) was described in the literature by Moglioni et al. (1998) and Noland et al. (1979), but a crystal structure has not been reported previously. It is the constituent of many pyrolysis oils and its characterization for environmental analysis. It also represents a useful model substance for MS and NMR analysis, and structural data are important for the understanding of some fine details of MS and NMR spectra.