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The title compound, C20H18O3, was prepared in a one-step synthesis by intramolecular cyclization following the sigmatropic rearrangement of the allyl aryl ether intermediate. The room-temperature crystal structure determination reveals a cis conformation of the ring annellation.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536800018821/cf6004sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536800018821/cf6004Isup2.hkl
Contains datablock I

CCDC reference: 155879

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.052
  • wR factor = 0.158
  • Data-to-parameter ratio = 28.0

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


Amber Alert Alert Level B:
ABSMU_01 Alert B The ratio of given/expected absorption coefficient lies outside the range 0.95 <> 1.05 Calculated value of mu = 0.085 Value of mu given = 0.090
0 Alert Level A = Potentially serious problem
1 Alert Level B = Potential problem
0 Alert Level C = Please check

Comment top

In the title compound, (I), the cyclopentyl and phenyl groups form angles of 65.85 (5) and 52.78 (4)° to the indene moiety, respectively. Two molecules form a centrosymmetrically related pair, with an interplanar distance of 3.60 Å between the indene units. A distorted herring-bone arrangement of the indene rings characterizes the packing.

Experimental top

The preparation of the title compound is described in detail by Novák et al. (1997).

Computing details top

Data collection: CAD-4 EXPRESS (Enraf-Nonius, 1994); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms, 1996); program(s) used to solve structure: SHELXS86 (Sheldrick, 1985); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ZORTEP (Zsolnay & Pritzkow, 1996); software used to prepare material for publication: SHELXL97.

Figures top
[Figure 1] Fig. 1. The molecular structure of (I) with 50% probability ellipsoids.
6,7-dimethyl-3a,8a-dihydro-3H-8-oxa-cyclopenta[a]inden-5-yl benzoate top
Crystal data top
C20H18O3F(000) = 648
Mr = 306.34Dx = 1.277 Mg m3
Monoclinic, P21/aMo Kα radiation, λ = 0.71070 Å
a = 7.9964 (10) ÅCell parameters from 25 reflections
b = 18.6031 (10) Åθ = 10.0–20.9°
c = 10.9254 (10) ŵ = 0.09 mm1
β = 101.274 (5)°T = 293 K
V = 1593.9 (2) Å3Needle, colourless
Z = 40.50 × 0.50 × 0.17 mm
Data collection top
Enraf-Nonius CAD-4
diffractometer
3130 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.017
Graphite monochromatorθmax = 33.0°, θmin = 2.8°
ω–2θ scansh = 012
Absorption correction: ψ scan
(MolEN; Enraf-Nonius, 1990)
k = 280
Tmin = 0.959, Tmax = 0.986l = 1616
6538 measured reflections3 standard reflections every 60 min
6020 independent reflections intensity decay: 2%
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.052Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.158H-atom parameters constrained
S = 0.97 w = 1/[σ2(Fo2) + (0.0815P)2 + 0.0559P] P = (Fo2 + 2Fc2)/3
6020 reflections(Δ/σ)max = 0.009
215 parametersΔρmax = 0.30 e Å3
0 restraintsΔρmin = 0.22 e Å3
Crystal data top
C20H18O3V = 1593.9 (2) Å3
Mr = 306.34Z = 4
Monoclinic, P21/aMo Kα radiation
a = 7.9964 (10) ŵ = 0.09 mm1
b = 18.6031 (10) ÅT = 293 K
c = 10.9254 (10) Å0.50 × 0.50 × 0.17 mm
β = 101.274 (5)°
Data collection top
Enraf-Nonius CAD-4
diffractometer
3130 reflections with I > 2σ(I)
Absorption correction: ψ scan
(MolEN; Enraf-Nonius, 1990)
Rint = 0.017
Tmin = 0.959, Tmax = 0.9863 standard reflections every 60 min
6538 measured reflections intensity decay: 2%
6020 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0520 restraints
wR(F2) = 0.158H-atom parameters constrained
S = 0.97Δρmax = 0.30 e Å3
6020 reflectionsΔρmin = 0.22 e Å3
215 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
xyzUiso*/Ueq
C10.7761 (2)0.08635 (10)0.14329 (16)0.0646 (4)
H10.83300.04960.11070.077 (4)*
C20.8519 (2)0.13357 (11)0.22675 (15)0.0708 (5)
H20.96810.13320.26030.077 (4)*
C30.7317 (3)0.18685 (10)0.26071 (16)0.0752 (5)
H3B0.75340.23430.23040.093 (4)*
H3C0.74110.18900.35050.093 (4)*
C3A0.5559 (2)0.15973 (8)0.19726 (13)0.0544 (3)
H3A0.48650.19830.15210.067 (3)*
C3B0.46054 (18)0.11964 (7)0.28143 (11)0.0442 (3)
C40.40996 (18)0.14021 (7)0.39023 (11)0.0461 (3)
H40.43050.18640.42220.067 (2)*
C50.32755 (17)0.08942 (7)0.44976 (11)0.0419 (3)
C60.29346 (14)0.01958 (6)0.40612 (11)0.0397 (3)
C70.34546 (16)0.00099 (7)0.29558 (11)0.0418 (3)
C7A0.42922 (16)0.05029 (7)0.23805 (10)0.0418 (3)
O80.49083 (13)0.03627 (5)0.13135 (8)0.0532 (3)
C8A0.5893 (2)0.09911 (8)0.10792 (12)0.0536 (3)
H8A0.55730.11450.02070.067 (3)*
C90.20783 (19)0.03354 (8)0.47702 (14)0.0555 (4)
H9A0.20440.01460.55820.118 (3)*
H9B0.27070.07780.48570.118 (3)*
H9C0.09370.04220.43250.118 (3)*
C100.3153 (2)0.07549 (8)0.24169 (16)0.0612 (4)
H10A0.37040.08030.17160.118 (3)*
H10B0.19500.08340.21510.118 (3)*
H10C0.36110.11030.30410.118 (3)*
O110.28707 (13)0.10569 (5)0.56712 (8)0.0492 (2)
O120.10692 (15)0.19461 (6)0.49072 (9)0.0662 (3)
C130.17338 (16)0.15775 (6)0.57653 (11)0.0408 (3)
C140.14310 (15)0.16360 (6)0.70628 (11)0.0382 (2)
C150.04804 (19)0.22128 (7)0.73546 (13)0.0510 (3)
H150.00480.25480.67440.067 (2)*
C160.0174 (2)0.22905 (9)0.85491 (14)0.0617 (4)
H160.04510.26810.87440.067 (2)*
C170.0794 (2)0.17900 (9)0.94495 (13)0.0589 (4)
H170.05820.18411.02520.067 (2)*
C180.1728 (2)0.12130 (8)0.91680 (12)0.0538 (3)
H180.21420.08750.97800.067 (2)*
C190.20536 (17)0.11335 (7)0.79753 (12)0.0452 (3)
H190.26880.07440.77880.067 (2)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0676 (10)0.0669 (10)0.0656 (9)0.0013 (8)0.0284 (8)0.0013 (8)
C20.0680 (10)0.0845 (12)0.0632 (10)0.0166 (9)0.0207 (8)0.0069 (9)
C30.1016 (14)0.0658 (10)0.0679 (10)0.0321 (10)0.0406 (10)0.0094 (8)
C3A0.0759 (10)0.0441 (7)0.0499 (7)0.0013 (7)0.0282 (7)0.0079 (6)
C3B0.0562 (7)0.0385 (6)0.0406 (6)0.0043 (5)0.0165 (5)0.0042 (5)
C40.0619 (8)0.0354 (6)0.0446 (6)0.0039 (6)0.0188 (6)0.0012 (5)
C50.0483 (7)0.0433 (6)0.0364 (5)0.0093 (5)0.0140 (5)0.0009 (5)
C60.0355 (6)0.0421 (6)0.0424 (6)0.0036 (5)0.0099 (5)0.0032 (5)
C70.0403 (6)0.0416 (6)0.0434 (6)0.0002 (5)0.0084 (5)0.0033 (5)
C7A0.0474 (7)0.0451 (6)0.0344 (5)0.0033 (5)0.0114 (5)0.0024 (5)
O80.0683 (6)0.0546 (6)0.0417 (5)0.0038 (5)0.0230 (4)0.0079 (4)
C8A0.0699 (9)0.0569 (8)0.0386 (6)0.0020 (7)0.0219 (6)0.0037 (6)
C90.0531 (8)0.0520 (8)0.0672 (9)0.0010 (6)0.0262 (7)0.0083 (7)
C100.0666 (9)0.0502 (8)0.0702 (10)0.0145 (7)0.0214 (8)0.0183 (7)
O110.0620 (6)0.0508 (5)0.0385 (4)0.0172 (4)0.0194 (4)0.0037 (4)
O120.0805 (8)0.0724 (7)0.0483 (6)0.0334 (6)0.0189 (5)0.0146 (5)
C130.0435 (6)0.0385 (6)0.0421 (6)0.0017 (5)0.0123 (5)0.0000 (5)
C140.0400 (6)0.0366 (5)0.0394 (5)0.0011 (5)0.0110 (4)0.0030 (5)
C150.0580 (8)0.0459 (7)0.0504 (7)0.0093 (6)0.0140 (6)0.0017 (6)
C160.0731 (10)0.0570 (9)0.0600 (8)0.0125 (8)0.0258 (7)0.0121 (7)
C170.0699 (10)0.0675 (9)0.0434 (7)0.0039 (8)0.0208 (6)0.0100 (7)
C180.0638 (9)0.0580 (8)0.0403 (6)0.0017 (7)0.0118 (6)0.0040 (6)
C190.0506 (7)0.0422 (6)0.0444 (6)0.0037 (5)0.0133 (5)0.0017 (5)
Geometric parameters (Å, º) top
C1—C21.324 (2)C7—C7A1.3850 (17)
C1—C8A1.487 (2)C7—C101.5067 (19)
C2—C31.478 (3)C7A—O81.3762 (13)
C3—C3A1.526 (2)O8—C8A1.4597 (17)
C3A—C3B1.5024 (18)O11—C131.3459 (14)
C3A—C8A1.548 (2)O12—C131.1986 (14)
C3B—C7A1.3804 (17)C13—C141.4880 (16)
C3B—C41.3824 (17)C14—C191.3862 (17)
C4—C51.3848 (17)C14—C151.3877 (17)
C5—C61.3925 (17)C15—C161.3816 (19)
C5—O111.4151 (14)C16—C171.375 (2)
C6—C71.4051 (16)C17—C181.376 (2)
C6—C91.5009 (17)C18—C191.3858 (17)
C2—C1—C8A111.98 (16)O8—C7A—C3B113.38 (11)
C1—C2—C3112.64 (17)O8—C7A—C7122.61 (11)
C2—C3—C3A104.53 (14)C3B—C7A—C7124.01 (11)
C3B—C3A—C3114.75 (12)C7A—O8—C8A106.95 (9)
C3B—C3A—C8A101.25 (11)O8—C8A—C1112.05 (12)
C3—C3A—C8A105.66 (13)O8—C8A—C3A107.90 (10)
C7A—C3B—C4119.34 (12)C1—C8A—C3A103.93 (13)
C7A—C3B—C3A109.48 (11)C13—O11—C5120.04 (9)
C4—C3B—C3A131.12 (12)O12—C13—O11123.69 (11)
C3B—C4—C5117.46 (12)O12—C13—C14124.99 (11)
C4—C5—C6123.71 (11)O11—C13—C14111.31 (10)
C4—C5—O11119.59 (11)C19—C14—C15119.48 (11)
C6—C5—O11116.47 (11)C19—C14—C13122.24 (11)
C5—C6—C7118.51 (11)C15—C14—C13118.28 (11)
C5—C6—C9121.07 (11)C16—C15—C14120.28 (13)
C7—C6—C9120.39 (11)C17—C16—C15119.95 (13)
C7A—C7—C6116.95 (11)C16—C17—C18120.26 (13)
C7A—C7—C10120.73 (11)C17—C18—C19120.22 (13)
C6—C7—C10122.32 (12)C18—C19—C14119.81 (12)

Experimental details

Crystal data
Chemical formulaC20H18O3
Mr306.34
Crystal system, space groupMonoclinic, P21/a
Temperature (K)293
a, b, c (Å)7.9964 (10), 18.6031 (10), 10.9254 (10)
β (°) 101.274 (5)
V3)1593.9 (2)
Z4
Radiation typeMo Kα
µ (mm1)0.09
Crystal size (mm)0.50 × 0.50 × 0.17
Data collection
DiffractometerEnraf-Nonius CAD-4
diffractometer
Absorption correctionψ scan
(MolEN; Enraf-Nonius, 1990)
Tmin, Tmax0.959, 0.986
No. of measured, independent and
observed [I > 2σ(I)] reflections
6538, 6020, 3130
Rint0.017
(sin θ/λ)max1)0.766
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.052, 0.158, 0.97
No. of reflections6020
No. of parameters215
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.30, 0.22

Computer programs: CAD-4 EXPRESS (Enraf-Nonius, 1994), CAD-4 EXPRESS, XCAD4 (Harms, 1996), SHELXS86 (Sheldrick, 1985), SHELXL97 (Sheldrick, 1997), ZORTEP (Zsolnay & Pritzkow, 1996), SHELXL97.

Selected geometric parameters (Å, º) top
C1—C21.324 (2)C7A—O81.3762 (13)
C2—C31.478 (3)O8—C8A1.4597 (17)
C3A—C8A1.548 (2)O11—C131.3459 (14)
C3B—C7A1.3804 (17)O12—C131.1986 (14)
C5—O111.4151 (14)
C1—C2—C3112.64 (17)O8—C7A—C7122.61 (11)
C3B—C3A—C3114.75 (12)O8—C8A—C1112.05 (12)
C4—C3B—C3A131.12 (12)C13—O11—C5120.04 (9)
O8—C7A—C3B113.38 (11)O12—C13—O11123.69 (11)
 

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