Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536800018821/cf6004sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536800018821/cf6004Isup2.hkl |
CCDC reference: 155879
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (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
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
The preparation of the title compound is described in detail by Novák et al. (1997).
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.
C20H18O3 | F(000) = 648 |
Mr = 306.34 | Dx = 1.277 Mg m−3 |
Monoclinic, P21/a | Mo Kα radiation, λ = 0.71070 Å |
a = 7.9964 (10) Å | Cell parameters from 25 reflections |
b = 18.6031 (10) Å | θ = 10.0–20.9° |
c = 10.9254 (10) Å | µ = 0.09 mm−1 |
β = 101.274 (5)° | T = 293 K |
V = 1593.9 (2) Å3 | Needle, colourless |
Z = 4 | 0.50 × 0.50 × 0.17 mm |
Enraf-Nonius CAD-4 diffractometer | 3130 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.017 |
Graphite monochromator | θmax = 33.0°, θmin = 2.8° |
ω–2θ scans | h = 0→12 |
Absorption correction: ψ scan (MolEN; Enraf-Nonius, 1990) | k = −28→0 |
Tmin = 0.959, Tmax = 0.986 | l = −16→16 |
6538 measured reflections | 3 standard reflections every 60 min |
6020 independent reflections | intensity decay: 2% |
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)] = 0.052 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.158 | H-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 parameters | Δρmax = 0.30 e Å−3 |
0 restraints | Δρmin = −0.22 e Å−3 |
C20H18O3 | V = 1593.9 (2) Å3 |
Mr = 306.34 | Z = 4 |
Monoclinic, P21/a | Mo Kα radiation |
a = 7.9964 (10) Å | µ = 0.09 mm−1 |
b = 18.6031 (10) Å | T = 293 K |
c = 10.9254 (10) Å | 0.50 × 0.50 × 0.17 mm |
β = 101.274 (5)° |
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 = 0.986 | 3 standard reflections every 60 min |
6538 measured reflections | intensity decay: 2% |
6020 independent reflections |
R[F2 > 2σ(F2)] = 0.052 | 0 restraints |
wR(F2) = 0.158 | H-atom parameters constrained |
S = 0.97 | Δρmax = 0.30 e Å−3 |
6020 reflections | Δρmin = −0.22 e Å−3 |
215 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 | 0.7761 (2) | 0.08635 (10) | 0.14329 (16) | 0.0646 (4) | |
H1 | 0.8330 | 0.0496 | 0.1107 | 0.077 (4)* | |
C2 | 0.8519 (2) | 0.13357 (11) | 0.22675 (15) | 0.0708 (5) | |
H2 | 0.9681 | 0.1332 | 0.2603 | 0.077 (4)* | |
C3 | 0.7317 (3) | 0.18685 (10) | 0.26071 (16) | 0.0752 (5) | |
H3B | 0.7534 | 0.2343 | 0.2304 | 0.093 (4)* | |
H3C | 0.7411 | 0.1890 | 0.3505 | 0.093 (4)* | |
C3A | 0.5559 (2) | 0.15973 (8) | 0.19726 (13) | 0.0544 (3) | |
H3A | 0.4865 | 0.1983 | 0.1521 | 0.067 (3)* | |
C3B | 0.46054 (18) | 0.11964 (7) | 0.28143 (11) | 0.0442 (3) | |
C4 | 0.40996 (18) | 0.14021 (7) | 0.39023 (11) | 0.0461 (3) | |
H4 | 0.4305 | 0.1864 | 0.4222 | 0.067 (2)* | |
C5 | 0.32755 (17) | 0.08942 (7) | 0.44976 (11) | 0.0419 (3) | |
C6 | 0.29346 (14) | 0.01958 (6) | 0.40612 (11) | 0.0397 (3) | |
C7 | 0.34546 (16) | −0.00099 (7) | 0.29558 (11) | 0.0418 (3) | |
C7A | 0.42922 (16) | 0.05029 (7) | 0.23805 (10) | 0.0418 (3) | |
O8 | 0.49083 (13) | 0.03627 (5) | 0.13135 (8) | 0.0532 (3) | |
C8A | 0.5893 (2) | 0.09911 (8) | 0.10792 (12) | 0.0536 (3) | |
H8A | 0.5573 | 0.1145 | 0.0207 | 0.067 (3)* | |
C9 | 0.20783 (19) | −0.03354 (8) | 0.47702 (14) | 0.0555 (4) | |
H9A | 0.2044 | −0.0146 | 0.5582 | 0.118 (3)* | |
H9B | 0.2707 | −0.0778 | 0.4857 | 0.118 (3)* | |
H9C | 0.0937 | −0.0422 | 0.4325 | 0.118 (3)* | |
C10 | 0.3153 (2) | −0.07549 (8) | 0.24169 (16) | 0.0612 (4) | |
H10A | 0.3704 | −0.0803 | 0.1716 | 0.118 (3)* | |
H10B | 0.1950 | −0.0834 | 0.2151 | 0.118 (3)* | |
H10C | 0.3611 | −0.1103 | 0.3041 | 0.118 (3)* | |
O11 | 0.28707 (13) | 0.10569 (5) | 0.56712 (8) | 0.0492 (2) | |
O12 | 0.10692 (15) | 0.19461 (6) | 0.49072 (9) | 0.0662 (3) | |
C13 | 0.17338 (16) | 0.15775 (6) | 0.57653 (11) | 0.0408 (3) | |
C14 | 0.14310 (15) | 0.16360 (6) | 0.70628 (11) | 0.0382 (2) | |
C15 | 0.04804 (19) | 0.22128 (7) | 0.73546 (13) | 0.0510 (3) | |
H15 | 0.0048 | 0.2548 | 0.6744 | 0.067 (2)* | |
C16 | 0.0174 (2) | 0.22905 (9) | 0.85491 (14) | 0.0617 (4) | |
H16 | −0.0451 | 0.2681 | 0.8744 | 0.067 (2)* | |
C17 | 0.0794 (2) | 0.17900 (9) | 0.94495 (13) | 0.0589 (4) | |
H17 | 0.0582 | 0.1841 | 1.0252 | 0.067 (2)* | |
C18 | 0.1728 (2) | 0.12130 (8) | 0.91680 (12) | 0.0538 (3) | |
H18 | 0.2142 | 0.0875 | 0.9780 | 0.067 (2)* | |
C19 | 0.20536 (17) | 0.11335 (7) | 0.79753 (12) | 0.0452 (3) | |
H19 | 0.2688 | 0.0744 | 0.7788 | 0.067 (2)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0676 (10) | 0.0669 (10) | 0.0656 (9) | 0.0013 (8) | 0.0284 (8) | 0.0013 (8) |
C2 | 0.0680 (10) | 0.0845 (12) | 0.0632 (10) | −0.0166 (9) | 0.0207 (8) | 0.0069 (9) |
C3 | 0.1016 (14) | 0.0658 (10) | 0.0679 (10) | −0.0321 (10) | 0.0406 (10) | −0.0094 (8) |
C3A | 0.0759 (10) | 0.0441 (7) | 0.0499 (7) | 0.0013 (7) | 0.0282 (7) | 0.0079 (6) |
C3B | 0.0562 (7) | 0.0385 (6) | 0.0406 (6) | 0.0043 (5) | 0.0165 (5) | 0.0042 (5) |
C4 | 0.0619 (8) | 0.0354 (6) | 0.0446 (6) | 0.0039 (6) | 0.0188 (6) | −0.0012 (5) |
C5 | 0.0483 (7) | 0.0433 (6) | 0.0364 (5) | 0.0093 (5) | 0.0140 (5) | 0.0009 (5) |
C6 | 0.0355 (6) | 0.0421 (6) | 0.0424 (6) | 0.0036 (5) | 0.0099 (5) | 0.0032 (5) |
C7 | 0.0403 (6) | 0.0416 (6) | 0.0434 (6) | −0.0002 (5) | 0.0084 (5) | −0.0033 (5) |
C7A | 0.0474 (7) | 0.0451 (6) | 0.0344 (5) | 0.0033 (5) | 0.0114 (5) | −0.0024 (5) |
O8 | 0.0683 (6) | 0.0546 (6) | 0.0417 (5) | −0.0038 (5) | 0.0230 (4) | −0.0079 (4) |
C8A | 0.0699 (9) | 0.0569 (8) | 0.0386 (6) | −0.0020 (7) | 0.0219 (6) | 0.0037 (6) |
C9 | 0.0531 (8) | 0.0520 (8) | 0.0672 (9) | −0.0010 (6) | 0.0262 (7) | 0.0083 (7) |
C10 | 0.0666 (9) | 0.0502 (8) | 0.0702 (10) | −0.0145 (7) | 0.0214 (8) | −0.0183 (7) |
O11 | 0.0620 (6) | 0.0508 (5) | 0.0385 (4) | 0.0172 (4) | 0.0194 (4) | 0.0037 (4) |
O12 | 0.0805 (8) | 0.0724 (7) | 0.0483 (6) | 0.0334 (6) | 0.0189 (5) | 0.0146 (5) |
C13 | 0.0435 (6) | 0.0385 (6) | 0.0421 (6) | 0.0017 (5) | 0.0123 (5) | 0.0000 (5) |
C14 | 0.0400 (6) | 0.0366 (5) | 0.0394 (5) | −0.0011 (5) | 0.0110 (4) | −0.0030 (5) |
C15 | 0.0580 (8) | 0.0459 (7) | 0.0504 (7) | 0.0093 (6) | 0.0140 (6) | −0.0017 (6) |
C16 | 0.0731 (10) | 0.0570 (9) | 0.0600 (8) | 0.0125 (8) | 0.0258 (7) | −0.0121 (7) |
C17 | 0.0699 (10) | 0.0675 (9) | 0.0434 (7) | −0.0039 (8) | 0.0208 (6) | −0.0100 (7) |
C18 | 0.0638 (9) | 0.0580 (8) | 0.0403 (6) | −0.0017 (7) | 0.0118 (6) | 0.0040 (6) |
C19 | 0.0506 (7) | 0.0422 (6) | 0.0444 (6) | 0.0037 (5) | 0.0133 (5) | 0.0017 (5) |
C1—C2 | 1.324 (2) | C7—C7A | 1.3850 (17) |
C1—C8A | 1.487 (2) | C7—C10 | 1.5067 (19) |
C2—C3 | 1.478 (3) | C7A—O8 | 1.3762 (13) |
C3—C3A | 1.526 (2) | O8—C8A | 1.4597 (17) |
C3A—C3B | 1.5024 (18) | O11—C13 | 1.3459 (14) |
C3A—C8A | 1.548 (2) | O12—C13 | 1.1986 (14) |
C3B—C7A | 1.3804 (17) | C13—C14 | 1.4880 (16) |
C3B—C4 | 1.3824 (17) | C14—C19 | 1.3862 (17) |
C4—C5 | 1.3848 (17) | C14—C15 | 1.3877 (17) |
C5—C6 | 1.3925 (17) | C15—C16 | 1.3816 (19) |
C5—O11 | 1.4151 (14) | C16—C17 | 1.375 (2) |
C6—C7 | 1.4051 (16) | C17—C18 | 1.376 (2) |
C6—C9 | 1.5009 (17) | C18—C19 | 1.3858 (17) |
C2—C1—C8A | 111.98 (16) | O8—C7A—C3B | 113.38 (11) |
C1—C2—C3 | 112.64 (17) | O8—C7A—C7 | 122.61 (11) |
C2—C3—C3A | 104.53 (14) | C3B—C7A—C7 | 124.01 (11) |
C3B—C3A—C3 | 114.75 (12) | C7A—O8—C8A | 106.95 (9) |
C3B—C3A—C8A | 101.25 (11) | O8—C8A—C1 | 112.05 (12) |
C3—C3A—C8A | 105.66 (13) | O8—C8A—C3A | 107.90 (10) |
C7A—C3B—C4 | 119.34 (12) | C1—C8A—C3A | 103.93 (13) |
C7A—C3B—C3A | 109.48 (11) | C13—O11—C5 | 120.04 (9) |
C4—C3B—C3A | 131.12 (12) | O12—C13—O11 | 123.69 (11) |
C3B—C4—C5 | 117.46 (12) | O12—C13—C14 | 124.99 (11) |
C4—C5—C6 | 123.71 (11) | O11—C13—C14 | 111.31 (10) |
C4—C5—O11 | 119.59 (11) | C19—C14—C15 | 119.48 (11) |
C6—C5—O11 | 116.47 (11) | C19—C14—C13 | 122.24 (11) |
C5—C6—C7 | 118.51 (11) | C15—C14—C13 | 118.28 (11) |
C5—C6—C9 | 121.07 (11) | C16—C15—C14 | 120.28 (13) |
C7—C6—C9 | 120.39 (11) | C17—C16—C15 | 119.95 (13) |
C7A—C7—C6 | 116.95 (11) | C16—C17—C18 | 120.26 (13) |
C7A—C7—C10 | 120.73 (11) | C17—C18—C19 | 120.22 (13) |
C6—C7—C10 | 122.32 (12) | C18—C19—C14 | 119.81 (12) |
Experimental details
Crystal data | |
Chemical formula | C20H18O3 |
Mr | 306.34 |
Crystal system, space group | Monoclinic, P21/a |
Temperature (K) | 293 |
a, b, c (Å) | 7.9964 (10), 18.6031 (10), 10.9254 (10) |
β (°) | 101.274 (5) |
V (Å3) | 1593.9 (2) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.09 |
Crystal size (mm) | 0.50 × 0.50 × 0.17 |
Data collection | |
Diffractometer | Enraf-Nonius CAD-4 diffractometer |
Absorption correction | ψ scan (MolEN; Enraf-Nonius, 1990) |
Tmin, Tmax | 0.959, 0.986 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 6538, 6020, 3130 |
Rint | 0.017 |
(sin θ/λ)max (Å−1) | 0.766 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.052, 0.158, 0.97 |
No. of reflections | 6020 |
No. of parameters | 215 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 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.
C1—C2 | 1.324 (2) | C7A—O8 | 1.3762 (13) |
C2—C3 | 1.478 (3) | O8—C8A | 1.4597 (17) |
C3A—C8A | 1.548 (2) | O11—C13 | 1.3459 (14) |
C3B—C7A | 1.3804 (17) | O12—C13 | 1.1986 (14) |
C5—O11 | 1.4151 (14) | ||
C1—C2—C3 | 112.64 (17) | O8—C7A—C7 | 122.61 (11) |
C3B—C3A—C3 | 114.75 (12) | O8—C8A—C1 | 112.05 (12) |
C4—C3B—C3A | 131.12 (12) | C13—O11—C5 | 120.04 (9) |
O8—C7A—C3B | 113.38 (11) | O12—C13—O11 | 123.69 (11) |
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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.