Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536801020323/na6111sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536801020323/na6111Isup2.hkl |
CCDC reference: 180527
The synthesis of 2,5-dicarboethoxy-3,4-diphenylcyclopentadienone can be carried out in a two-step process. Diethyl acetonedicarboxylate is reacted with benzil in sodium ethoxide/ethanol to provide a yellow ionic precipitate. The yellow precipitate is reacted with sulfuric acid in acetic anhydride to produce the title compound as an orange product (Reinhardt, 1973).
H-atom positions were calculated at the begining of each least-squares refinement using geometric considerations and additively constrained. Methyl, methylene, and aromatic H-atom positions used fixed C—H bond lengths of 0.96, 0.97, and 0.93 Å, respectively. In all cases, the H-atom Uiso is 1.3 times the Uiso of the attached atom and were not refined. Atom C23 is observed to have large thermal motion in all directions, which at first was thought to be due to disorder. An extensive effort was made to resolve this situation to an unsuccessful end. Residual electron density is present in the vicinity of C23, however the position of this density does not lend itself to the needed geometry for an alternate C23 atom.
Data collection: CAD-4 Software (Enraf-Nonius, 1989); cell refinement: CAD-4 Software; data reduction: XCAD (McArdle, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEX (McArdle, 1995); software used to prepare material for publication: OSCAIL (McArdle, 1995).
C23H20O5 | F(000) = 792 |
Mr = 376.39 | Dx = 1.263 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71069 Å |
Hall symbol: -P 2ybc | Cell parameters from 25 reflections |
a = 10.697 (3) Å | θ = 3.0–12.6° |
b = 18.228 (4) Å | µ = 0.09 mm−1 |
c = 11.202 (2) Å | T = 293 K |
β = 115.02 (2)° | Trigonal prism, orange |
V = 1979.2 (9) Å3 | 0.40 × 0.35 × 0.30 mm |
Z = 4 |
Enraf-Nonius CAD-4 diffractometer | Rint = 0.016 |
Radiation source: fine-focus sealed tube | θmax = 30.0°, θmin = 2.1° |
Graphite monochromator | h = −15→13 |
ω/2θ scans | k = −6→25 |
6973 measured reflections | l = −2→15 |
5758 independent reflections | 3 standard reflections every 120 min |
2719 reflections with I > 2σ(I) | intensity decay: 1.0% |
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)] = 0.064 | H-atom parameters constrained |
wR(F2) = 0.219 | w = 1/[σ2(Fo2) + (0.122P)2] where P = (Fo2 + 2Fc2)/3 |
S = 0.98 | (Δ/σ)max = 0.001 |
5758 reflections | Δρmax = 0.40 e Å−3 |
254 parameters | Δρmin = −0.30 e Å−3 |
0 restraints | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.009 (2) |
C23H20O5 | V = 1979.2 (9) Å3 |
Mr = 376.39 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 10.697 (3) Å | µ = 0.09 mm−1 |
b = 18.228 (4) Å | T = 293 K |
c = 11.202 (2) Å | 0.40 × 0.35 × 0.30 mm |
β = 115.02 (2)° |
Enraf-Nonius CAD-4 diffractometer | Rint = 0.016 |
6973 measured reflections | 3 standard reflections every 120 min |
5758 independent reflections | intensity decay: 1.0% |
2719 reflections with I > 2σ(I) |
R[F2 > 2σ(F2)] = 0.064 | 0 restraints |
wR(F2) = 0.219 | H-atom parameters constrained |
S = 0.98 | Δρmax = 0.40 e Å−3 |
5758 reflections | Δρmin = −0.30 e Å−3 |
254 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 | ||
O1 | 0.75673 (18) | 0.89668 (8) | 0.53580 (15) | 0.0702 (5) | |
O21 | 0.9292 (2) | 0.83882 (11) | 0.82297 (17) | 0.0969 (7) | |
O51 | 0.5134 (2) | 0.81968 (12) | 0.18481 (16) | 0.0958 (7) | |
O21A | 1.05064 (18) | 0.75724 (12) | 0.77260 (19) | 0.0955 (7) | |
O51A | 0.44631 (19) | 0.86856 (10) | 0.32745 (15) | 0.0814 (5) | |
C1 | 0.7381 (2) | 0.83118 (11) | 0.52632 (18) | 0.0520 (5) | |
C2 | 0.8206 (2) | 0.77374 (10) | 0.62324 (17) | 0.0503 (5) | |
C3 | 0.77219 (19) | 0.70738 (10) | 0.57229 (17) | 0.0450 (4) | |
C4 | 0.65171 (18) | 0.71815 (10) | 0.43731 (16) | 0.0451 (4) | |
C5 | 0.6335 (2) | 0.79020 (10) | 0.41181 (18) | 0.0507 (4) | |
C21 | 0.9370 (2) | 0.79372 (12) | 0.7496 (2) | 0.0596 (5) | |
C22 | 1.1716 (4) | 0.7711 (3) | 0.8975 (4) | 0.1250 (14) | |
H22A | 1.2551 | 0.7611 | 0.8864 | 0.162* | |
H22B | 1.1730 | 0.8224 | 0.9212 | 0.162* | |
C23 | 1.1692 (6) | 0.7274 (3) | 0.9988 (6) | 0.217 (4) | |
H23A | 1.2487 | 0.7378 | 1.0791 | 0.325* | |
H23B | 1.1701 | 0.6766 | 0.9765 | 0.325* | |
H23C | 1.0870 | 0.7376 | 1.0105 | 0.325* | |
C31 | 0.82355 (18) | 0.63537 (10) | 0.63091 (17) | 0.0457 (4) | |
C32 | 0.8567 (2) | 0.62374 (12) | 0.76381 (19) | 0.0566 (5) | |
H32 | 0.8428 | 0.6610 | 0.8137 | 0.074* | |
C33 | 0.9104 (2) | 0.55692 (14) | 0.8220 (2) | 0.0698 (6) | |
H33 | 0.9319 | 0.5493 | 0.9106 | 0.091* | |
C34 | 0.9316 (3) | 0.50236 (13) | 0.7494 (3) | 0.0719 (7) | |
H34 | 0.9685 | 0.4578 | 0.7893 | 0.093* | |
C35 | 0.8990 (2) | 0.51246 (11) | 0.6179 (2) | 0.0637 (6) | |
H35 | 0.9134 | 0.4749 | 0.5690 | 0.083* | |
C36 | 0.8444 (2) | 0.57904 (10) | 0.5584 (2) | 0.0539 (5) | |
H36 | 0.8217 | 0.5858 | 0.4693 | 0.070* | |
C41 | 0.56613 (19) | 0.65799 (10) | 0.35568 (16) | 0.0471 (4) | |
C42 | 0.5056 (2) | 0.60732 (12) | 0.40744 (19) | 0.0574 (5) | |
H42 | 0.5224 | 0.6099 | 0.4959 | 0.075* | |
C43 | 0.4208 (2) | 0.55328 (13) | 0.3285 (2) | 0.0703 (6) | |
H43 | 0.3793 | 0.5201 | 0.3636 | 0.091* | |
C44 | 0.3971 (3) | 0.54810 (15) | 0.1986 (2) | 0.0772 (7) | |
H44 | 0.3387 | 0.5119 | 0.1456 | 0.100* | |
C45 | 0.4595 (3) | 0.59618 (15) | 0.1467 (2) | 0.0773 (7) | |
H45 | 0.4458 | 0.5916 | 0.0594 | 0.101* | |
C46 | 0.5428 (2) | 0.65138 (12) | 0.22429 (18) | 0.0618 (6) | |
H46 | 0.5836 | 0.6844 | 0.1883 | 0.080* | |
C51 | 0.5264 (2) | 0.82703 (11) | 0.29502 (19) | 0.0566 (5) | |
C52 | 0.3375 (3) | 0.90908 (18) | 0.2210 (3) | 0.0922 (9) | |
H52A | 0.3774 | 0.9392 | 0.1747 | 0.120* | |
H52B | 0.2731 | 0.8751 | 0.1585 | 0.120* | |
C53 | 0.2662 (4) | 0.9550 (2) | 0.2784 (3) | 0.1231 (13) | |
H53A | 0.1944 | 0.9820 | 0.2099 | 0.185* | |
H53B | 0.3305 | 0.9887 | 0.3396 | 0.185* | |
H53C | 0.2265 | 0.9248 | 0.3236 | 0.185* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0928 (12) | 0.0439 (8) | 0.0624 (9) | −0.0065 (7) | 0.0217 (8) | 0.0000 (6) |
O21 | 0.1056 (15) | 0.0908 (13) | 0.0645 (10) | 0.0102 (11) | 0.0072 (10) | −0.0316 (10) |
O51 | 0.1232 (17) | 0.1125 (15) | 0.0516 (9) | 0.0380 (13) | 0.0370 (10) | 0.0252 (9) |
O21A | 0.0559 (9) | 0.1252 (17) | 0.0797 (12) | −0.0046 (10) | 0.0038 (8) | −0.0377 (11) |
O51A | 0.0874 (12) | 0.0984 (13) | 0.0474 (8) | 0.0409 (10) | 0.0179 (8) | 0.0163 (8) |
C1 | 0.0614 (12) | 0.0478 (11) | 0.0443 (9) | −0.0018 (9) | 0.0199 (9) | −0.0003 (8) |
C2 | 0.0548 (11) | 0.0485 (10) | 0.0416 (9) | −0.0037 (8) | 0.0145 (8) | −0.0024 (8) |
C3 | 0.0474 (9) | 0.0477 (10) | 0.0368 (8) | 0.0000 (8) | 0.0146 (7) | −0.0006 (7) |
C4 | 0.0471 (10) | 0.0468 (10) | 0.0370 (8) | −0.0029 (8) | 0.0133 (7) | 0.0009 (7) |
C5 | 0.0567 (11) | 0.0488 (10) | 0.0406 (9) | 0.0006 (9) | 0.0149 (8) | 0.0031 (7) |
C21 | 0.0638 (13) | 0.0534 (12) | 0.0492 (10) | −0.0075 (10) | 0.0118 (9) | −0.0082 (9) |
C22 | 0.0789 (19) | 0.164 (4) | 0.085 (2) | −0.007 (2) | −0.0116 (17) | −0.039 (2) |
C23 | 0.182 (5) | 0.157 (4) | 0.152 (4) | 0.011 (4) | −0.083 (4) | −0.014 (4) |
C31 | 0.0416 (9) | 0.0455 (10) | 0.0425 (9) | −0.0022 (7) | 0.0106 (7) | 0.0020 (7) |
C32 | 0.0560 (12) | 0.0613 (12) | 0.0446 (10) | 0.0051 (9) | 0.0135 (8) | 0.0049 (8) |
C33 | 0.0707 (14) | 0.0759 (15) | 0.0533 (12) | 0.0115 (12) | 0.0171 (11) | 0.0195 (11) |
C34 | 0.0639 (14) | 0.0606 (14) | 0.0787 (15) | 0.0135 (11) | 0.0179 (12) | 0.0218 (11) |
C35 | 0.0621 (13) | 0.0515 (12) | 0.0729 (14) | 0.0074 (10) | 0.0241 (11) | −0.0002 (10) |
C36 | 0.0548 (11) | 0.0521 (11) | 0.0501 (10) | 0.0009 (9) | 0.0175 (9) | −0.0018 (8) |
C41 | 0.0452 (9) | 0.0506 (10) | 0.0376 (8) | −0.0007 (8) | 0.0099 (7) | −0.0017 (7) |
C42 | 0.0618 (12) | 0.0622 (12) | 0.0457 (10) | −0.0088 (10) | 0.0202 (9) | −0.0018 (9) |
C43 | 0.0679 (14) | 0.0638 (14) | 0.0723 (14) | −0.0179 (11) | 0.0228 (12) | −0.0032 (11) |
C44 | 0.0749 (16) | 0.0743 (16) | 0.0626 (14) | −0.0215 (13) | 0.0098 (12) | −0.0169 (12) |
C45 | 0.0868 (17) | 0.0838 (17) | 0.0431 (10) | −0.0100 (14) | 0.0097 (11) | −0.0118 (11) |
C46 | 0.0704 (14) | 0.0690 (13) | 0.0410 (9) | −0.0108 (11) | 0.0186 (9) | −0.0038 (9) |
C51 | 0.0659 (13) | 0.0523 (11) | 0.0426 (9) | 0.0015 (10) | 0.0141 (9) | 0.0067 (8) |
C52 | 0.0868 (18) | 0.102 (2) | 0.0631 (14) | 0.0373 (16) | 0.0077 (13) | 0.0232 (14) |
C53 | 0.103 (3) | 0.154 (3) | 0.110 (2) | 0.067 (2) | 0.042 (2) | 0.056 (2) |
O1—C1 | 1.208 (2) | C32—H32 | 0.9300 |
O21—C21 | 1.191 (3) | C33—C34 | 1.363 (4) |
O51—C51 | 1.190 (2) | C33—H33 | 0.9300 |
O21A—C21 | 1.312 (3) | C34—C35 | 1.376 (4) |
O21A—C22 | 1.472 (3) | C34—H34 | 0.9300 |
O51A—C51 | 1.305 (3) | C35—C36 | 1.389 (3) |
O51A—C52 | 1.466 (3) | C35—H35 | 0.9300 |
C1—C5 | 1.497 (3) | C36—H36 | 0.9300 |
C1—C2 | 1.498 (3) | C41—C42 | 1.388 (3) |
C2—C3 | 1.344 (3) | C41—C46 | 1.390 (2) |
C2—C21 | 1.482 (3) | C42—C43 | 1.377 (3) |
C3—C31 | 1.466 (3) | C42—H42 | 0.9300 |
C3—C4 | 1.529 (2) | C43—C44 | 1.371 (3) |
C4—C5 | 1.341 (3) | C43—H43 | 0.9300 |
C4—C41 | 1.473 (2) | C44—C45 | 1.371 (4) |
C5—C51 | 1.486 (3) | C44—H44 | 0.9300 |
C22—C23 | 1.396 (8) | C45—C46 | 1.381 (3) |
C22—H22A | 0.9700 | C45—H45 | 0.9300 |
C22—H22B | 0.9700 | C46—H46 | 0.9300 |
C23—H23A | 0.9600 | C52—C53 | 1.453 (4) |
C23—H23B | 0.9600 | C52—H52A | 0.9700 |
C23—H23C | 0.9600 | C52—H52B | 0.9700 |
C31—C36 | 1.385 (3) | C53—H53A | 0.9600 |
C31—C32 | 1.393 (3) | C53—H53B | 0.9600 |
C32—C33 | 1.386 (3) | C53—H53C | 0.9600 |
C21—O21A—C22 | 117.9 (2) | C33—C34—H34 | 119.6 |
C51—O51A—C52 | 117.05 (19) | C35—C34—H34 | 119.6 |
O1—C1—C5 | 127.19 (18) | C34—C35—C36 | 119.7 (2) |
O1—C1—C2 | 127.04 (18) | C34—C35—H35 | 120.1 |
C5—C1—C2 | 105.67 (15) | C36—C35—H35 | 120.1 |
C3—C2—C21 | 130.07 (17) | C31—C36—C35 | 120.38 (19) |
C3—C2—C1 | 108.55 (16) | C31—C36—H36 | 119.8 |
C21—C2—C1 | 121.34 (17) | C35—C36—H36 | 119.8 |
C2—C3—C31 | 127.68 (16) | C42—C41—C46 | 118.55 (18) |
C2—C3—C4 | 108.45 (15) | C42—C41—C4 | 120.89 (16) |
C31—C3—C4 | 123.87 (15) | C46—C41—C4 | 120.55 (18) |
C5—C4—C41 | 126.93 (17) | C43—C42—C41 | 120.32 (19) |
C5—C4—C3 | 108.81 (15) | C43—C42—H42 | 119.8 |
C41—C4—C3 | 124.14 (16) | C41—C42—H42 | 119.8 |
C4—C5—C51 | 128.24 (17) | C44—C43—C42 | 120.4 (2) |
C4—C5—C1 | 108.51 (16) | C44—C43—H43 | 119.8 |
C51—C5—C1 | 123.20 (16) | C42—C43—H43 | 119.8 |
O21—C21—O21A | 123.0 (2) | C43—C44—C45 | 120.1 (2) |
O21—C21—C2 | 123.6 (2) | C43—C44—H44 | 119.9 |
O21A—C21—C2 | 113.45 (18) | C45—C44—H44 | 119.9 |
C23—C22—O21A | 111.3 (4) | C44—C45—C46 | 119.9 (2) |
C23—C22—H22A | 109.4 | C44—C45—H45 | 120.0 |
O21A—C22—H22A | 109.4 | C46—C45—H45 | 120.0 |
C23—C22—H22B | 109.4 | C45—C46—C41 | 120.6 (2) |
O21A—C22—H22B | 109.4 | C45—C46—H46 | 119.7 |
H22A—C22—H22B | 108.0 | C41—C46—H46 | 119.7 |
C22—C23—H23A | 109.5 | O51—C51—O51A | 123.5 (2) |
C22—C23—H23B | 109.5 | O51—C51—C5 | 124.8 (2) |
H23A—C23—H23B | 109.5 | O51A—C51—C5 | 111.68 (17) |
C22—C23—H23C | 109.5 | C53—C52—O51A | 108.4 (2) |
H23A—C23—H23C | 109.5 | C53—C52—H52A | 110.0 |
H23B—C23—H23C | 109.5 | O51A—C52—H52A | 110.0 |
C36—C31—C32 | 118.87 (18) | C53—C52—H52B | 110.0 |
C36—C31—C3 | 121.59 (16) | O51A—C52—H52B | 110.0 |
C32—C31—C3 | 119.51 (17) | H52A—C52—H52B | 108.4 |
C33—C32—C31 | 120.3 (2) | C52—C53—H53A | 109.5 |
C33—C32—H32 | 119.9 | C52—C53—H53B | 109.5 |
C31—C32—H32 | 119.9 | H53A—C53—H53B | 109.5 |
C34—C33—C32 | 120.0 (2) | C52—C53—H53C | 109.5 |
C34—C33—H33 | 120.0 | H53A—C53—H53C | 109.5 |
C32—C33—H33 | 120.0 | H53B—C53—H53C | 109.5 |
C33—C34—C35 | 120.7 (2) | ||
O1—C1—C2—C3 | −176.0 (2) | C2—C3—C31—C32 | 43.9 (3) |
C5—C1—C2—C3 | 0.6 (2) | C4—C3—C31—C32 | −137.09 (19) |
O1—C1—C2—C21 | 2.2 (3) | C36—C31—C32—C33 | 0.3 (3) |
C5—C1—C2—C21 | 178.81 (19) | C3—C31—C32—C33 | −177.54 (19) |
C21—C2—C3—C31 | 0.3 (4) | C31—C32—C33—C34 | 0.4 (3) |
C1—C2—C3—C31 | 178.37 (18) | C32—C33—C34—C35 | −0.7 (4) |
C21—C2—C3—C4 | −178.8 (2) | C33—C34—C35—C36 | 0.3 (4) |
C1—C2—C3—C4 | −0.7 (2) | C32—C31—C36—C35 | −0.7 (3) |
C2—C3—C4—C5 | 0.7 (2) | C3—C31—C36—C35 | 177.09 (19) |
C31—C3—C4—C5 | −178.46 (17) | C34—C35—C36—C31 | 0.4 (3) |
C2—C3—C4—C41 | −175.48 (18) | C5—C4—C41—C42 | −123.7 (2) |
C31—C3—C4—C41 | 5.4 (3) | C3—C4—C41—C42 | 51.8 (3) |
C41—C4—C5—C51 | −1.8 (4) | C5—C4—C41—C46 | 55.4 (3) |
C3—C4—C5—C51 | −177.83 (19) | C3—C4—C41—C46 | −129.1 (2) |
C41—C4—C5—C1 | 175.72 (18) | C46—C41—C42—C43 | −2.1 (3) |
C3—C4—C5—C1 | −0.3 (2) | C4—C41—C42—C43 | 177.1 (2) |
O1—C1—C5—C4 | 176.5 (2) | C41—C42—C43—C44 | 1.2 (4) |
C2—C1—C5—C4 | −0.1 (2) | C42—C43—C44—C45 | 0.9 (4) |
O1—C1—C5—C51 | −5.9 (4) | C43—C44—C45—C46 | −2.1 (4) |
C2—C1—C5—C51 | 177.54 (19) | C44—C45—C46—C41 | 1.2 (4) |
C22—O21A—C21—O21 | 2.4 (4) | C42—C41—C46—C45 | 0.9 (3) |
C22—O21A—C21—C2 | −178.1 (3) | C4—C41—C46—C45 | −178.2 (2) |
C3—C2—C21—O21 | −132.6 (3) | C52—O51A—C51—O51 | −1.5 (4) |
C1—C2—C21—O21 | 49.6 (3) | C52—O51A—C51—C5 | 179.0 (2) |
C3—C2—C21—O21A | 47.9 (3) | C4—C5—C51—O51 | −62.3 (4) |
C1—C2—C21—O21A | −129.9 (2) | C1—C5—C51—O51 | 120.6 (3) |
C21—O21A—C22—C23 | 86.2 (5) | C4—C5—C51—O51A | 117.2 (2) |
C2—C3—C31—C36 | −133.9 (2) | C1—C5—C51—O51A | −59.9 (3) |
C4—C3—C31—C36 | 45.1 (3) | C51—O51A—C52—C53 | −176.5 (3) |
Experimental details
Crystal data | |
Chemical formula | C23H20O5 |
Mr | 376.39 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 293 |
a, b, c (Å) | 10.697 (3), 18.228 (4), 11.202 (2) |
β (°) | 115.02 (2) |
V (Å3) | 1979.2 (9) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.09 |
Crystal size (mm) | 0.40 × 0.35 × 0.30 |
Data collection | |
Diffractometer | Enraf-Nonius CAD-4 diffractometer |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 6973, 5758, 2719 |
Rint | 0.016 |
(sin θ/λ)max (Å−1) | 0.704 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.064, 0.219, 0.98 |
No. of reflections | 5758 |
No. of parameters | 254 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.40, −0.30 |
Computer programs: CAD-4 Software (Enraf-Nonius, 1989), CAD-4 Software, XCAD (McArdle, 1995), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEX (McArdle, 1995), OSCAIL (McArdle, 1995).
O1—C1 | 1.208 (2) | C2—C3 | 1.344 (3) |
O21—C21 | 1.191 (3) | C2—C21 | 1.482 (3) |
O51—C51 | 1.190 (2) | C3—C31 | 1.466 (3) |
O21A—C21 | 1.312 (3) | C3—C4 | 1.529 (2) |
O21A—C22 | 1.472 (3) | C4—C5 | 1.341 (3) |
O51A—C51 | 1.305 (3) | C4—C41 | 1.473 (2) |
O51A—C52 | 1.466 (3) | C5—C51 | 1.486 (3) |
C1—C5 | 1.497 (3) | C22—C23 | 1.396 (8) |
C1—C2 | 1.498 (3) | C52—C53 | 1.453 (4) |
C21—O21A—C22 | 117.9 (2) | C41—C4—C3 | 124.14 (16) |
C51—O51A—C52 | 117.05 (19) | C4—C5—C51 | 128.24 (17) |
O1—C1—C5 | 127.19 (18) | C4—C5—C1 | 108.51 (16) |
O1—C1—C2 | 127.04 (18) | C51—C5—C1 | 123.20 (16) |
C5—C1—C2 | 105.67 (15) | O21—C21—O21A | 123.0 (2) |
C3—C2—C21 | 130.07 (17) | O21—C21—C2 | 123.6 (2) |
C3—C2—C1 | 108.55 (16) | O21A—C21—C2 | 113.45 (18) |
C21—C2—C1 | 121.34 (17) | C23—C22—O21A | 111.3 (4) |
C2—C3—C31 | 127.68 (16) | O51—C51—O51A | 123.5 (2) |
C2—C3—C4 | 108.45 (15) | O51—C51—C5 | 124.8 (2) |
C31—C3—C4 | 123.87 (15) | O51A—C51—C5 | 111.68 (17) |
C5—C4—C41 | 126.93 (17) | C53—C52—O51A | 108.4 (2) |
C5—C4—C3 | 108.81 (15) | ||
O1—C1—C5—C51 | −5.9 (4) | C5—C4—C41—C42 | −123.7 (2) |
C22—O21A—C21—C2 | −178.1 (3) | C52—O51A—C51—C5 | 179.0 (2) |
C3—C2—C21—O21 | −132.6 (3) | C4—C5—C51—O51 | −62.3 (4) |
C21—O21A—C22—C23 | 86.2 (5) | C51—O51A—C52—C53 | −176.5 (3) |
C2—C3—C31—C36 | −133.9 (2) |
Cyclopentadienones produced by a condensation reaction are the building blocks used to produce many monomers used for light emitting diodes. These cyclones can participate in Diels-Alder reactions with a large variety of internal and terminal acetylenes to generate a multitude of aromatic compounds.
The title compound, (I), reacts smoothly with alkynes to generate aromatic terephthalic esters having phenyl and alkyl substituents. Reduction of the esters to alcohols and further conversion to the corresponding chloro compounds provides poly(phenylene vinylene) (PPV) monomers. (Feld et al., 1998) Polymeric material produced from these monomers exhibit photoluminescence at 490 nm with an efficiency of 65%. These materials are useful for designing multicolor electroluminescent devices. In addition, the terephthalic esters are a convenient substrate for the generation of substituted 5,8-dioxo-5,8-dihydroindeno[2,1-c]fluorine ring system by reaction with sulfuric acid. (Lorge, 1998)
The cyclopentadienone and phenyl ring systems found are themselves planar, but are not coplanar. The phenyl rings are twisted about the external bond to the five-membered ring by 44.68 (12)° for ring 1 (C31–C36) and 53.91 (12)° for ring 2 (C41–C46). The bond distances and angles around each atom are within accepted values.