Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680102116X/cf6135sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S160053680102116X/cf6135Isup2.hkl |
CCDC reference: 180550
Spiro[1,1a,6,6a-tetrahydro-cyclopropa[a]indene-1,1'-2',3'-dihydro-1'H-indene] was synthesized through the aldol condensation of 1H-indan-1-one and the Huang-Minlon reduction of the self-condensation product according to the method of Bell & Spanswick (1966). It 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.
Data collection: COLLECT (Nonius, 1998); cell refinement: DENZO and SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO (Otwinowski & Minor, 1997) 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).
Fig. 1. View of the title compound (XP; Sheldrick, 1991) showing the labelling of all non-H atoms. Displacement ellipsoids are shown at the 50% probability level. |
C18H16 | F(000) = 496 |
Mr = 232.31 | Dx = 1.188 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 7.0256 (1) Å | Cell parameters from 13022 reflections |
b = 12.5288 (2) Å | θ = 3.2–27.5° |
c = 14.8003 (4) Å | µ = 0.07 mm−1 |
β = 94.3527 (9)° | T = 291 K |
V = 1299.00 (4) Å3 | Block, colourless |
Z = 4 | 0.48 × 0.45 × 0.15 mm |
Nonius KappaCCD diffractometer | 1842 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.031 |
Graphite monochromator | θmax = 27.5°, θmin = 3.2° |
Detector resolution: 10 vertical, 18 horizontal pixels mm-1 | h = −9→9 |
318 frames via ω–rotation (Δω=1°) with 3 sets at different κ–angles and two times 60 s per frame scans | k = −16→16 |
13022 measured reflections | l = −19→19 |
2965 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)] = 0.046 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.140 | H-atom parameters constrained |
S = 1.07 | w = 1/[σ2(Fo2) + (0.0785P)2] where P = (Fo2 + 2Fc2)/3 |
2965 reflections | (Δ/σ)max = 0.001 |
163 parameters | Δρmax = 0.21 e Å−3 |
0 restraints | Δρmin = −0.16 e Å−3 |
C18H16 | V = 1299.00 (4) Å3 |
Mr = 232.31 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 7.0256 (1) Å | µ = 0.07 mm−1 |
b = 12.5288 (2) Å | T = 291 K |
c = 14.8003 (4) Å | 0.48 × 0.45 × 0.15 mm |
β = 94.3527 (9)° |
Nonius KappaCCD diffractometer | 1842 reflections with I > 2σ(I) |
13022 measured reflections | Rint = 0.031 |
2965 independent reflections |
R[F2 > 2σ(F2)] = 0.046 | 0 restraints |
wR(F2) = 0.140 | H-atom parameters constrained |
S = 1.07 | Δρmax = 0.21 e Å−3 |
2965 reflections | Δρmin = −0.16 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 | 0.28206 (18) | 0.87197 (10) | 0.14870 (9) | 0.0475 (3) | |
C2 | 0.4409 (2) | 0.91286 (11) | 0.09391 (11) | 0.0645 (4) | |
H2A | 0.3991 | 0.9758 | 0.0597 | 0.077* | |
H2B | 0.5520 | 0.9316 | 0.1337 | 0.077* | |
C3 | 0.4894 (2) | 0.82389 (12) | 0.03024 (12) | 0.0705 (5) | |
H3A | 0.4617 | 0.8453 | −0.0324 | 0.085* | |
H3B | 0.6235 | 0.8053 | 0.0393 | 0.085* | |
C4 | 0.36662 (18) | 0.73145 (10) | 0.05319 (9) | 0.0495 (3) | |
C5 | 0.3579 (2) | 0.63003 (11) | 0.01622 (10) | 0.0571 (4) | |
H5 | 0.4353 | 0.6118 | −0.0296 | 0.068* | |
C6 | 0.2336 (2) | 0.55618 (11) | 0.04777 (10) | 0.0597 (4) | |
H6 | 0.2265 | 0.4880 | 0.0229 | 0.072* | |
C7 | 0.1196 (2) | 0.58315 (11) | 0.11616 (11) | 0.0642 (4) | |
H7 | 0.0370 | 0.5326 | 0.1375 | 0.077* | |
C8 | 0.1266 (2) | 0.68398 (11) | 0.15324 (10) | 0.0597 (4) | |
H8 | 0.0493 | 0.7017 | 0.1993 | 0.072* | |
C9 | 0.25020 (18) | 0.75890 (10) | 0.12115 (8) | 0.0469 (3) | |
C11 | 0.10924 (19) | 0.94012 (10) | 0.16884 (9) | 0.0518 (4) | |
H11 | −0.0184 | 0.9081 | 0.1653 | 0.062* | |
C12 | 0.25542 (19) | 0.90745 (10) | 0.24399 (9) | 0.0526 (4) | |
H12 | 0.2196 | 0.8542 | 0.2881 | 0.063* | |
C13 | 0.3586 (2) | 1.00735 (10) | 0.27835 (10) | 0.0607 (4) | |
H13A | 0.3354 | 1.0209 | 0.3411 | 0.073* | |
H13B | 0.4950 | 1.0008 | 0.2735 | 0.073* | |
C14 | 0.27603 (19) | 1.09545 (10) | 0.21772 (9) | 0.0504 (4) | |
C15 | 0.3254 (2) | 1.20237 (11) | 0.21720 (10) | 0.0593 (4) | |
H15 | 0.4257 | 1.2279 | 0.2559 | 0.071* | |
C16 | 0.2234 (2) | 1.27060 (11) | 0.15832 (10) | 0.0646 (4) | |
H16 | 0.2533 | 1.3429 | 0.1585 | 0.078* | |
C17 | 0.0788 (2) | 1.23301 (12) | 0.09972 (11) | 0.0664 (4) | |
H17 | 0.0116 | 1.2800 | 0.0605 | 0.080* | |
C18 | 0.0316 (2) | 1.12559 (12) | 0.09822 (10) | 0.0633 (4) | |
H18 | −0.0651 | 1.1000 | 0.0575 | 0.076* | |
C19 | 0.13018 (19) | 1.05687 (11) | 0.15813 (9) | 0.0503 (4) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0525 (8) | 0.0421 (7) | 0.0492 (8) | −0.0002 (6) | 0.0125 (6) | 0.0018 (5) |
C2 | 0.0696 (10) | 0.0523 (9) | 0.0754 (10) | −0.0099 (7) | 0.0297 (8) | −0.0032 (7) |
C3 | 0.0780 (11) | 0.0596 (10) | 0.0784 (11) | −0.0031 (8) | 0.0359 (9) | −0.0025 (8) |
C4 | 0.0523 (8) | 0.0448 (8) | 0.0520 (8) | 0.0019 (6) | 0.0071 (6) | 0.0016 (6) |
C5 | 0.0621 (9) | 0.0534 (8) | 0.0558 (9) | 0.0104 (7) | 0.0059 (7) | −0.0050 (6) |
C6 | 0.0655 (9) | 0.0435 (8) | 0.0689 (10) | 0.0052 (7) | −0.0032 (8) | −0.0047 (6) |
C7 | 0.0666 (10) | 0.0463 (8) | 0.0804 (11) | −0.0084 (7) | 0.0097 (8) | 0.0019 (7) |
C8 | 0.0643 (9) | 0.0521 (9) | 0.0651 (9) | −0.0037 (7) | 0.0201 (7) | 0.0011 (6) |
C9 | 0.0492 (7) | 0.0419 (7) | 0.0500 (7) | 0.0012 (6) | 0.0066 (6) | 0.0018 (5) |
C11 | 0.0499 (8) | 0.0459 (8) | 0.0604 (9) | 0.0003 (6) | 0.0108 (6) | −0.0019 (6) |
C12 | 0.0647 (9) | 0.0485 (8) | 0.0453 (8) | −0.0023 (6) | 0.0088 (6) | 0.0034 (6) |
C13 | 0.0748 (10) | 0.0563 (9) | 0.0500 (8) | 0.0017 (7) | −0.0026 (7) | −0.0009 (6) |
C14 | 0.0552 (8) | 0.0483 (8) | 0.0482 (8) | 0.0064 (6) | 0.0072 (6) | −0.0015 (6) |
C15 | 0.0636 (9) | 0.0530 (9) | 0.0614 (9) | −0.0036 (7) | 0.0054 (7) | −0.0063 (7) |
C16 | 0.0771 (11) | 0.0458 (8) | 0.0727 (10) | 0.0044 (8) | 0.0165 (8) | 0.0018 (7) |
C17 | 0.0754 (11) | 0.0536 (9) | 0.0701 (10) | 0.0175 (8) | 0.0046 (8) | 0.0073 (7) |
C18 | 0.0580 (9) | 0.0618 (9) | 0.0686 (10) | 0.0131 (7) | −0.0047 (7) | −0.0034 (7) |
C19 | 0.0499 (8) | 0.0504 (8) | 0.0512 (8) | 0.0047 (6) | 0.0079 (6) | −0.0042 (6) |
C1—C9 | 1.4863 (17) | C8—H8 | 0.930 |
C1—C12 | 1.5040 (18) | C11—C19 | 1.4798 (19) |
C1—C2 | 1.5176 (18) | C11—C12 | 1.5119 (19) |
C1—C11 | 1.5321 (19) | C11—H11 | 0.980 |
C2—C3 | 1.515 (2) | C12—C13 | 1.5148 (18) |
C2—H2A | 0.970 | C12—H12 | 0.980 |
C2—H2B | 0.970 | C13—C14 | 1.5103 (18) |
C3—C4 | 1.4985 (19) | C13—H13A | 0.970 |
C3—H3A | 0.970 | C13—H13B | 0.970 |
C3—H3B | 0.970 | C14—C15 | 1.3840 (18) |
C4—C5 | 1.3830 (18) | C14—C19 | 1.3872 (18) |
C4—C9 | 1.3871 (18) | C15—C16 | 1.3818 (19) |
C5—C6 | 1.3779 (19) | C15—H15 | 0.930 |
C5—H5 | 0.930 | C16—C17 | 1.368 (2) |
C6—C7 | 1.379 (2) | C16—H16 | 0.930 |
C6—H6 | 0.930 | C17—C18 | 1.386 (2) |
C7—C8 | 1.3768 (19) | C17—H17 | 0.930 |
C7—H7 | 0.930 | C18—C19 | 1.3835 (19) |
C8—C9 | 1.3869 (18) | C18—H18 | 0.930 |
C9—C1—C12 | 120.80 (11) | C19—C11—C12 | 106.19 (11) |
C9—C1—C2 | 106.07 (10) | C19—C11—C1 | 116.32 (11) |
C12—C1—C2 | 123.38 (12) | C12—C11—C1 | 59.21 (9) |
C9—C1—C11 | 118.65 (11) | C19—C11—H11 | 119.8 |
C12—C1—C11 | 59.73 (9) | C12—C11—H11 | 119.8 |
C2—C1—C11 | 122.80 (11) | C1—C11—H11 | 119.8 |
C3—C2—C1 | 107.05 (11) | C1—C12—C11 | 61.06 (9) |
C3—C2—H2A | 110.3 | C1—C12—C13 | 117.94 (11) |
C1—C2—H2A | 110.3 | C11—C12—C13 | 107.72 (11) |
C3—C2—H2B | 110.3 | C1—C12—H12 | 118.7 |
C1—C2—H2B | 110.3 | C11—C12—H12 | 118.7 |
H2A—C2—H2B | 108.6 | C13—C12—H12 | 118.7 |
C4—C3—C2 | 105.50 (12) | C14—C13—C12 | 104.59 (11) |
C4—C3—H3A | 110.6 | C14—C13—H13A | 110.8 |
C2—C3—H3A | 110.6 | C12—C13—H13A | 110.8 |
C4—C3—H3B | 110.6 | C14—C13—H13B | 110.8 |
C2—C3—H3B | 110.6 | C12—C13—H13B | 110.8 |
H3A—C3—H3B | 108.8 | H13A—C13—H13B | 108.9 |
C5—C4—C9 | 120.24 (12) | C15—C14—C19 | 120.48 (12) |
C5—C4—C3 | 129.02 (13) | C15—C14—C13 | 128.71 (13) |
C9—C4—C3 | 110.73 (11) | C19—C14—C13 | 110.79 (12) |
C6—C5—C4 | 119.56 (13) | C16—C15—C14 | 118.94 (13) |
C6—C5—H5 | 120.2 | C16—C15—H15 | 120.5 |
C4—C5—H5 | 120.2 | C14—C15—H15 | 120.5 |
C5—C6—C7 | 120.15 (13) | C17—C16—C15 | 120.76 (13) |
C5—C6—H6 | 119.9 | C17—C16—H16 | 119.6 |
C7—C6—H6 | 119.9 | C15—C16—H16 | 119.6 |
C8—C7—C6 | 120.80 (13) | C16—C17—C18 | 120.64 (14) |
C8—C7—H7 | 119.6 | C16—C17—H17 | 119.7 |
C6—C7—H7 | 119.6 | C18—C17—H17 | 119.7 |
C7—C8—C9 | 119.27 (13) | C19—C18—C17 | 119.11 (14) |
C7—C8—H8 | 120.4 | C19—C18—H18 | 120.4 |
C9—C8—H8 | 120.4 | C17—C18—H18 | 120.4 |
C8—C9—C4 | 119.97 (12) | C18—C19—C14 | 120.02 (13) |
C8—C9—C1 | 129.51 (12) | C18—C19—C11 | 129.41 (13) |
C4—C9—C1 | 110.51 (11) | C14—C19—C11 | 110.54 (11) |
C9—C1—C2—C3 | 3.82 (17) | C9—C1—C12—C11 | −107.36 (13) |
C12—C1—C2—C3 | 149.71 (13) | C2—C1—C12—C11 | 111.50 (14) |
C11—C1—C2—C3 | −137.37 (14) | C9—C1—C12—C13 | 156.89 (12) |
C1—C2—C3—C4 | −3.31 (18) | C2—C1—C12—C13 | 15.74 (19) |
C2—C3—C4—C5 | −178.70 (14) | C11—C1—C12—C13 | −95.76 (13) |
C2—C3—C4—C9 | 1.57 (18) | C19—C11—C12—C1 | −111.37 (11) |
C9—C4—C5—C6 | −0.4 (2) | C19—C11—C12—C13 | 1.30 (14) |
C3—C4—C5—C6 | 179.87 (14) | C1—C11—C12—C13 | 112.67 (12) |
C4—C5—C6—C7 | −0.4 (2) | C1—C12—C13—C14 | 62.88 (16) |
C5—C6—C7—C8 | 0.6 (2) | C11—C12—C13—C14 | −3.19 (15) |
C6—C7—C8—C9 | −0.1 (2) | C12—C13—C14—C15 | −177.13 (13) |
C7—C8—C9—C4 | −0.8 (2) | C12—C13—C14—C19 | 4.15 (16) |
C7—C8—C9—C1 | 179.10 (13) | C19—C14—C15—C16 | 1.9 (2) |
C5—C4—C9—C8 | 1.0 (2) | C13—C14—C15—C16 | −176.67 (14) |
C3—C4—C9—C8 | −179.23 (13) | C14—C15—C16—C17 | −1.6 (2) |
C5—C4—C9—C1 | −178.88 (12) | C15—C16—C17—C18 | 0.0 (2) |
C3—C4—C9—C1 | 0.88 (16) | C16—C17—C18—C19 | 1.3 (2) |
C12—C1—C9—C8 | 30.2 (2) | C17—C18—C19—C14 | −1.0 (2) |
C2—C1—C9—C8 | 177.17 (14) | C17—C18—C19—C11 | −178.91 (13) |
C11—C1—C9—C8 | −39.7 (2) | C15—C14—C19—C18 | −0.7 (2) |
C12—C1—C9—C4 | −149.92 (12) | C13—C14—C19—C18 | 178.19 (12) |
C2—C1—C9—C4 | −2.96 (15) | C15—C14—C19—C11 | 177.66 (11) |
C11—C1—C9—C4 | 140.15 (12) | C13—C14—C19—C11 | −3.50 (15) |
C9—C1—C11—C19 | −155.23 (11) | C12—C11—C19—C18 | 179.44 (14) |
C12—C1—C11—C19 | 93.87 (12) | C1—C11—C19—C18 | 116.25 (16) |
C2—C1—C11—C19 | −18.57 (19) | C12—C11—C19—C14 | 1.33 (14) |
C9—C1—C11—C12 | 110.90 (13) | C1—C11—C19—C14 | −61.87 (15) |
C2—C1—C11—C12 | −112.44 (15) |
Experimental details
Crystal data | |
Chemical formula | C18H16 |
Mr | 232.31 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 291 |
a, b, c (Å) | 7.0256 (1), 12.5288 (2), 14.8003 (4) |
β (°) | 94.3527 (9) |
V (Å3) | 1299.00 (4) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.07 |
Crystal size (mm) | 0.48 × 0.45 × 0.15 |
Data collection | |
Diffractometer | Nonius KappaCCD diffractometer |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 13022, 2965, 1842 |
Rint | 0.031 |
(sin θ/λ)max (Å−1) | 0.649 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.046, 0.140, 1.07 |
No. of reflections | 2965 |
No. of parameters | 163 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.21, −0.16 |
Computer programs: COLLECT (Nonius, 1998), DENZO and SCALEPACK (Otwinowski & Minor, 1997), DENZO (Otwinowski & Minor, 1997) and SCALEPACK, SHELXS97 (Sheldrick, 1990), SHELXL97 (Sheldrick, 1997), SHELXTL-Plus (Sheldrick, 1991), SHELXL97, PARST95 (Nardelli, 1995) and PLATON (Spek, 2001).
In the course of our investigations on the four possible biindenylidene isomers, we have already reported a second modification of (E)-2,3,2',3'-tetrahydro-[1,1']biindenylidene (Jovanovic et al., 2001a) and the crystal structure of 1,3,1',3'-tetrahydro-[2,2']biindenylidene (Jovanovic et al., 2001b). We wished next to determine the crystal structure of 2,3,1',3'-tetrahydro-[1,2']-biindenylidene, (I), and synthesized it following the description of Bell & Spanswick (1966). The compound we obtained had the same melting point and molecular weight as previously reported for the structure (I), but our crystallographic investigations show that it actually has the structure (II).