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The crystal structures of three 1:2 inclusion compounds that consist of host molecule 2,5-diphenylhydroquinone (C
18H
14O
2) and the guest molecules 2-pyridone (C
5H
5NO), 1,3-diphenyl-2-propen-1-one (chalcone, C
15H
12O) and 1-(4-methoxyphenyl)-3-phenyl-2-propen-1-one (4′-methoxychalcone, C
16H
14O
2) were determined in order to study the ability of guest molecules in inclusion compounds to undergo photoreaction. All of the crystals were found to be photoresistant. The three inclusion compounds crystallize in triclinic space group
. In each case, the host/guest ratio is 1:2, with the host molecules occupying crystallographic centers of symmetry and the guest molecules occupying general positions. The guest molecules in each of the inclusion compounds are linked to the host molecules by hydrogen bonds. In the inclusion compound where the guest molecule is pyridone, the host molecule is disordered so that the hydroxy groups are distributed between two different sites, with occupancies of 0.738 (3) and 0.262 (3). The pyridone molecules form dimers
via N—H
O hydrogen bonds.
Supporting information
CCDC references: 231070; 231071; 231072
The host component was synthesized according to the method of Toda (1989). The purification of 2,5-diphenylhydroquinone was checked by comparing its 1H NMR spectrum and melting-point value to those in the literature (Ohaba, 1997). The guest components in all three inclusion compounds were purchased from Sigma. Crystals of the inclusion compounds were obtained from ethyl acetate solutions of the host and guest in a 1:2 ratio by slow evaporation of the solvent at room temperature.
In all structures, hydroxy H atoms were located from difference Fourier maps and treated as riding. During the refinement of (I–a), the occupancies of the two hydroxy O atoms were free to refine. The H atom of the major O atom was located from a difference Fourier map; however, the minor O atom could not be detected.
For all compounds, data collection: Collect (Nonius, 2000); cell refinement: DENZO SMN (Otwinowski & Minor 1997); data reduction: DENZO SMN; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997).
(pyr0) 2,5-diphenylhydroquinone–2-pyridone (1/2)
top
Crystal data top
C18H14O2·2C5H5NO | Z = 1 |
Mr = 452.49 | F(000) = 238 |
Triclinic, P1 | Dx = 1.312 Mg m−3 |
a = 6.510 (1) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 8.971 (1) Å | Cell parameters from 2021 reflections |
c = 11.085 (2) Å | θ = 2.5–25.0° |
α = 70.746 (2)° | µ = 0.09 mm−1 |
β = 73.108 (2)° | T = 293 K |
γ = 73.807 (2)° | Prism, colorless |
V = 572.66 (15) Å3 | 0.3 × 0.2 × 0.1 mm |
Data collection top
Nonius KappaCCD diffractometer | 1611 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.000 |
Graphite monochromator | θmax = 25.0°, θmin = 2.5° |
Detector resolution: 95 pixels mm-1 | h = 0→7 |
ϕ scan | k = −9→10 |
2021 measured reflections | l = −12→13 |
2021 independent reflections | |
Refinement top
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)] = 0.042 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.126 | H-atom parameters constrained |
S = 1.06 | w = 1/[σ2(Fo2) + (0.07P)2 + 0.0744P] where P = (Fo2 + 2Fc2)/3 |
2021 reflections | (Δ/σ)max < 0.001 |
165 parameters | Δρmax = 0.12 e Å−3 |
0 restraints | Δρmin = −0.15 e Å−3 |
Crystal data top
C18H14O2·2C5H5NO | γ = 73.807 (2)° |
Mr = 452.49 | V = 572.66 (15) Å3 |
Triclinic, P1 | Z = 1 |
a = 6.510 (1) Å | Mo Kα radiation |
b = 8.971 (1) Å | µ = 0.09 mm−1 |
c = 11.085 (2) Å | T = 293 K |
α = 70.746 (2)° | 0.3 × 0.2 × 0.1 mm |
β = 73.108 (2)° | |
Data collection top
Nonius KappaCCD diffractometer | 1611 reflections with I > 2σ(I) |
2021 measured reflections | Rint = 0.000 |
2021 independent reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.042 | 0 restraints |
wR(F2) = 0.126 | H-atom parameters constrained |
S = 1.06 | Δρmax = 0.12 e Å−3 |
2021 reflections | Δρmin = −0.15 e Å−3 |
165 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 | x | y | z | Uiso*/Ueq | Occ. (<1) |
O1 | 1.1700 (2) | 0.70288 (18) | 0.06695 (14) | 0.0540 (5) | 0.738 (3) |
H1O1 | 1.2729 | 0.7309 | 0.0078 | 0.062 (7)* | 0.738 (3) |
O1A | 1.3794 (7) | 0.5964 (5) | −0.1382 (4) | 0.0607 (15) | 0.262 (3) |
C1 | 1.1955 (2) | 0.54401 (17) | −0.07399 (14) | 0.0438 (4) | |
C2 | 1.0863 (2) | 0.59945 (17) | 0.03575 (14) | 0.0427 (4) | |
C3 | 0.8884 (2) | 0.55622 (16) | 0.11220 (13) | 0.0405 (4) | |
C4 | 0.7711 (2) | 0.61203 (16) | 0.23101 (13) | 0.0415 (4) | |
C5 | 0.8831 (3) | 0.61239 (18) | 0.32024 (15) | 0.0496 (4) | |
H5 | 1.0348 | 0.5789 | 0.3048 | 0.059* | |
C6 | 0.7717 (3) | 0.6619 (2) | 0.43178 (16) | 0.0594 (5) | |
H6 | 0.8489 | 0.6607 | 0.4908 | 0.071* | |
C7 | 0.5472 (3) | 0.7130 (2) | 0.45612 (18) | 0.0643 (5) | |
H7 | 0.4728 | 0.7467 | 0.5310 | 0.077* | |
C8 | 0.4345 (3) | 0.7137 (2) | 0.36885 (18) | 0.0645 (5) | |
H8 | 0.2830 | 0.7483 | 0.3846 | 0.077* | |
C9 | 0.5440 (3) | 0.66333 (19) | 0.25790 (16) | 0.0529 (4) | |
H9 | 0.4650 | 0.6636 | 0.2001 | 0.064* | |
O2 | 0.53951 (19) | 0.12618 (16) | 0.08110 (12) | 0.0676 (4) | |
N1 | 0.2325 (2) | 0.03140 (15) | 0.11983 (13) | 0.0507 (4) | |
H1N | 0.2911 | −0.0085 | 0.0540 | 0.061* | |
C10 | 0.3493 (3) | 0.11471 (19) | 0.14868 (16) | 0.0505 (4) | |
C11 | 0.2426 (3) | 0.1799 (2) | 0.25613 (18) | 0.0623 (5) | |
H11 | 0.3126 | 0.2399 | 0.2798 | 0.075* | |
C12 | 0.0409 (3) | 0.1564 (2) | 0.3249 (2) | 0.0697 (5) | |
H12 | −0.0256 | 0.1998 | 0.3957 | 0.084* | |
C13 | −0.0701 (3) | 0.0679 (2) | 0.2918 (2) | 0.0664 (5) | |
H13 | −0.2088 | 0.0512 | 0.3398 | 0.080* | |
C14 | 0.0301 (3) | 0.00755 (19) | 0.18833 (18) | 0.0575 (4) | |
H14 | −0.0405 | −0.0511 | 0.1637 | 0.069* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0574 (10) | 0.0712 (10) | 0.0509 (9) | −0.0405 (8) | 0.0070 (7) | −0.0328 (7) |
O1A | 0.057 (3) | 0.071 (3) | 0.061 (3) | −0.023 (2) | 0.004 (2) | −0.033 (2) |
C1 | 0.0436 (8) | 0.0465 (8) | 0.0445 (8) | −0.0166 (6) | −0.0067 (6) | −0.0130 (6) |
C2 | 0.0454 (8) | 0.0442 (7) | 0.0450 (8) | −0.0188 (6) | −0.0080 (6) | −0.0143 (6) |
C3 | 0.0429 (8) | 0.0399 (7) | 0.0404 (8) | −0.0117 (6) | −0.0080 (6) | −0.0113 (6) |
C4 | 0.0457 (8) | 0.0391 (7) | 0.0400 (8) | −0.0135 (6) | −0.0053 (6) | −0.0104 (6) |
C5 | 0.0490 (9) | 0.0566 (9) | 0.0471 (9) | −0.0149 (7) | −0.0082 (7) | −0.0177 (7) |
C6 | 0.0686 (12) | 0.0719 (11) | 0.0464 (9) | −0.0203 (9) | −0.0098 (8) | −0.0246 (8) |
C7 | 0.0681 (12) | 0.0705 (11) | 0.0535 (10) | −0.0083 (9) | −0.0016 (9) | −0.0305 (9) |
C8 | 0.0508 (10) | 0.0748 (12) | 0.0622 (11) | 0.0000 (9) | −0.0042 (9) | −0.0291 (9) |
C9 | 0.0473 (9) | 0.0601 (9) | 0.0517 (9) | −0.0065 (7) | −0.0113 (7) | −0.0186 (7) |
O2 | 0.0564 (8) | 0.0936 (9) | 0.0644 (8) | −0.0416 (7) | 0.0094 (6) | −0.0342 (7) |
N1 | 0.0491 (8) | 0.0556 (8) | 0.0509 (8) | −0.0198 (6) | −0.0038 (6) | −0.0174 (6) |
C10 | 0.0494 (9) | 0.0554 (9) | 0.0490 (9) | −0.0212 (7) | −0.0049 (7) | −0.0134 (7) |
C11 | 0.0615 (11) | 0.0695 (11) | 0.0646 (11) | −0.0239 (9) | −0.0010 (9) | −0.0318 (9) |
C12 | 0.0659 (12) | 0.0715 (11) | 0.0714 (12) | −0.0173 (9) | 0.0079 (10) | −0.0360 (10) |
C13 | 0.0483 (10) | 0.0625 (11) | 0.0826 (13) | −0.0159 (8) | 0.0074 (9) | −0.0270 (9) |
C14 | 0.0461 (9) | 0.0528 (9) | 0.0753 (11) | −0.0174 (7) | −0.0073 (8) | −0.0186 (8) |
Geometric parameters (Å, º) top
O1—C2 | 1.3714 (18) | C7—H7 | 0.9300 |
O1—H1O1 | 0.8200 | C8—C9 | 1.379 (2) |
O1A—O1A | 0.000 (13) | C8—H8 | 0.9300 |
O1A—C1 | 1.326 (4) | C9—H9 | 0.9300 |
C1—O1A | 1.326 (4) | O2—C10 | 1.2597 (18) |
C1—C2 | 1.390 (2) | N1—C14 | 1.352 (2) |
C1—C3i | 1.3952 (19) | N1—C10 | 1.3616 (19) |
C2—C3 | 1.398 (2) | N1—H1N | 0.8600 |
C3—C1i | 1.3952 (19) | C10—C11 | 1.412 (2) |
C3—C4 | 1.4851 (19) | C11—C12 | 1.348 (2) |
C4—C5 | 1.390 (2) | C11—H11 | 0.9300 |
C4—C9 | 1.393 (2) | C12—C13 | 1.398 (3) |
C5—C6 | 1.383 (2) | C12—H12 | 0.9300 |
C5—H5 | 0.9300 | C13—C14 | 1.346 (3) |
C6—C7 | 1.377 (3) | C13—H13 | 0.9300 |
C6—H6 | 0.9300 | C14—H14 | 0.9300 |
C7—C8 | 1.371 (3) | | |
| | | |
C2—O1—H1O1 | 109.5 | C6—C7—H7 | 120.3 |
O1A—O1A—C1 | 0 (10) | C7—C8—C9 | 120.55 (17) |
O1A—C1—O1A | 0.0 (7) | C7—C8—H8 | 119.7 |
O1A—C1—C2 | 114.7 (2) | C9—C8—H8 | 119.7 |
O1A—C1—C2 | 114.7 (2) | C8—C9—C4 | 121.08 (16) |
O1A—C1—C3i | 124.0 (2) | C8—C9—H9 | 119.5 |
O1A—C1—C3i | 124.0 (2) | C4—C9—H9 | 119.5 |
C2—C1—C3i | 121.29 (13) | C14—N1—C10 | 123.97 (14) |
O1—C2—C1 | 119.42 (13) | C14—N1—H1N | 118.0 |
O1—C2—C3 | 119.39 (13) | C10—N1—H1N | 118.0 |
C1—C2—C3 | 121.15 (13) | O2—C10—N1 | 119.10 (14) |
C1i—C3—C2 | 117.56 (13) | O2—C10—C11 | 125.53 (14) |
C1i—C3—C4 | 120.47 (13) | N1—C10—C11 | 115.36 (14) |
C2—C3—C4 | 121.96 (12) | C12—C11—C10 | 120.94 (16) |
C5—C4—C9 | 117.71 (14) | C12—C11—H11 | 119.5 |
C5—C4—C3 | 121.29 (13) | C10—C11—H11 | 119.5 |
C9—C4—C3 | 120.99 (13) | C11—C12—C13 | 121.19 (17) |
C6—C5—C4 | 120.80 (15) | C11—C12—H12 | 119.4 |
C6—C5—H5 | 119.6 | C13—C12—H12 | 119.4 |
C4—C5—H5 | 119.6 | C14—C13—C12 | 117.92 (16) |
C7—C6—C5 | 120.54 (16) | C14—C13—H13 | 121.0 |
C7—C6—H6 | 119.7 | C12—C13—H13 | 121.0 |
C5—C6—H6 | 119.7 | C13—C14—N1 | 120.61 (16) |
C8—C7—C6 | 119.32 (16) | C13—C14—H14 | 119.7 |
C8—C7—H7 | 120.3 | N1—C14—H14 | 119.7 |
| | | |
O1A—O1A—C1—C2 | 0.0 (2) | C9—C4—C5—C6 | 0.1 (2) |
O1A—O1A—C1—C3i | 0.0 (3) | C3—C4—C5—C6 | −178.83 (14) |
O1A—C1—C2—O1 | 1.4 (3) | C4—C5—C6—C7 | −0.5 (3) |
O1A—C1—C2—O1 | 1.4 (3) | C5—C6—C7—C8 | 0.3 (3) |
C3i—C1—C2—O1 | −177.44 (14) | C6—C7—C8—C9 | 0.2 (3) |
O1A—C1—C2—C3 | 179.1 (3) | C7—C8—C9—C4 | −0.6 (3) |
O1A—C1—C2—C3 | 179.1 (3) | C5—C4—C9—C8 | 0.4 (2) |
C3i—C1—C2—C3 | 0.2 (2) | C3—C4—C9—C8 | 179.34 (14) |
O1—C2—C3—C1i | 177.45 (14) | C14—N1—C10—O2 | 177.92 (15) |
C1—C2—C3—C1i | −0.2 (2) | C14—N1—C10—C11 | −1.2 (2) |
O1—C2—C3—C4 | −3.3 (2) | O2—C10—C11—C12 | −177.81 (18) |
C1—C2—C3—C4 | 178.99 (13) | N1—C10—C11—C12 | 1.2 (3) |
C1i—C3—C4—C5 | 136.34 (15) | C10—C11—C12—C13 | −0.5 (3) |
C2—C3—C4—C5 | −42.9 (2) | C11—C12—C13—C14 | −0.4 (3) |
C1i—C3—C4—C9 | −42.6 (2) | C12—C13—C14—N1 | 0.5 (3) |
C2—C3—C4—C9 | 138.24 (15) | C10—N1—C14—C13 | 0.3 (3) |
Symmetry code: (i) −x+2, −y+1, −z. |
(Ib) 2,5-diphenylhydroquinone–1,3-diphenyl-2-propen-1-one (1/2)
top
Crystal data top
C18H14O2·2C15H12O | Z = 1 |
Mr = 678.78 | F(000) = 358 |
Triclinic, P1 | Dx = 1.243 Mg m−3 |
a = 9.413 (2) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 10.042 (2) Å | Cell parameters from 2649 reflections |
c = 11.848 (2) Å | θ = 1.0–25.1° |
α = 65.74 (2)° | µ = 0.08 mm−1 |
β = 81.57 (2)° | T = 293 K |
γ = 62.81 (2)° | Prism, yellow |
V = 907.0 (3) Å3 | 0.2 × 0.1 × 0.08 mm |
Data collection top
Nonius KappaCCD diffractometer | 1284 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.043 |
Graphite monochromator | θmax = 25.1°, θmin = 1.9° |
Detector resolution: 95 pixels mm-1 | h = −11→11 |
ϕ scan | k = −11→11 |
5064 measured reflections | l = −14→14 |
3153 independent reflections | |
Refinement top
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)] = 0.043 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.142 | H-atom parameters constrained |
S = 0.86 | w = 1/[σ2(Fo2) + (0.06P)2] where P = (Fo2 + 2Fc2)/3 |
3153 reflections | (Δ/σ)max = 0.001 |
239 parameters | Δρmax = 0.13 e Å−3 |
0 restraints | Δρmin = −0.18 e Å−3 |
Crystal data top
C18H14O2·2C15H12O | γ = 62.81 (2)° |
Mr = 678.78 | V = 907.0 (3) Å3 |
Triclinic, P1 | Z = 1 |
a = 9.413 (2) Å | Mo Kα radiation |
b = 10.042 (2) Å | µ = 0.08 mm−1 |
c = 11.848 (2) Å | T = 293 K |
α = 65.74 (2)° | 0.2 × 0.1 × 0.08 mm |
β = 81.57 (2)° | |
Data collection top
Nonius KappaCCD diffractometer | 1284 reflections with I > 2σ(I) |
5064 measured reflections | Rint = 0.043 |
3153 independent reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.043 | 0 restraints |
wR(F2) = 0.142 | H-atom parameters constrained |
S = 0.86 | Δρmax = 0.13 e Å−3 |
3153 reflections | Δρmin = −0.18 e Å−3 |
239 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 | x | y | z | Uiso*/Ueq | |
O1 | 0.1676 (2) | 0.1632 (3) | 0.50660 (18) | 0.0672 (7) | |
H1O1 | 0.1443 | 0.1867 | 0.5676 | 0.081* | |
C1 | −0.0184 (3) | 0.0479 (3) | 0.5955 (3) | 0.0505 (8) | |
H1 | −0.0303 | 0.0814 | 0.6602 | 0.061* | |
C2 | 0.0853 (3) | 0.0806 (3) | 0.5041 (3) | 0.0494 (8) | |
C3 | 0.1056 (3) | 0.0326 (3) | 0.4051 (3) | 0.0451 (7) | |
C4 | 0.2137 (3) | 0.0631 (3) | 0.3023 (3) | 0.0449 (7) | |
C5 | 0.3663 (3) | 0.0410 (3) | 0.3242 (3) | 0.0534 (8) | |
H5 | 0.3999 | 0.0142 | 0.4039 | 0.064* | |
C6 | 0.4681 (4) | 0.0588 (4) | 0.2275 (3) | 0.0583 (9) | |
H6 | 0.5696 | 0.0437 | 0.2429 | 0.070* | |
C7 | 0.4205 (4) | 0.0984 (4) | 0.1102 (3) | 0.0645 (9) | |
H7 | 0.4893 | 0.1095 | 0.0459 | 0.077* | |
C8 | 0.2715 (4) | 0.1214 (4) | 0.0880 (3) | 0.0642 (9) | |
H8 | 0.2390 | 0.1488 | 0.0078 | 0.077* | |
C9 | 0.1678 (3) | 0.1049 (3) | 0.1821 (3) | 0.0544 (8) | |
H9 | 0.0662 | 0.1219 | 0.1647 | 0.065* | |
O2 | 0.0980 (3) | 0.2331 (3) | 0.7198 (2) | 0.0797 (8) | |
C10 | 0.0585 (3) | 0.3326 (4) | 0.7678 (3) | 0.0554 (8) | |
C11 | −0.0664 (3) | 0.3394 (4) | 0.8608 (3) | 0.0517 (8) | |
C12 | −0.1360 (4) | 0.4604 (4) | 0.9064 (3) | 0.0677 (10) | |
H12 | −0.1056 | 0.5443 | 0.8778 | 0.081* | |
C13 | −0.2501 (4) | 0.4583 (4) | 0.9939 (3) | 0.0784 (11) | |
H13 | −0.2967 | 0.5410 | 1.0233 | 0.094* | |
C14 | −0.2948 (4) | 0.3346 (5) | 1.0373 (3) | 0.0798 (11) | |
H14 | −0.3718 | 0.3333 | 1.0961 | 0.096* | |
C15 | −0.2259 (4) | 0.2134 (5) | 0.9941 (3) | 0.0805 (11) | |
H15 | −0.2554 | 0.1287 | 1.0242 | 0.097* | |
C16 | −0.1134 (4) | 0.2157 (4) | 0.9065 (3) | 0.0675 (10) | |
H16 | −0.0679 | 0.1326 | 0.8773 | 0.081* | |
C17 | 0.1417 (4) | 0.4339 (4) | 0.7393 (3) | 0.0593 (9) | |
H17 | 0.101 (3) | 0.518 (3) | 0.763 (2) | 0.063 (10)* | |
C18 | 0.2875 (4) | 0.3916 (4) | 0.6980 (3) | 0.0577 (9) | |
H18 | 0.3302 | 0.2974 | 0.6824 | 0.069* | |
C19 | 0.3902 (4) | 0.4716 (4) | 0.6736 (3) | 0.0530 (8) | |
C20 | 0.5510 (4) | 0.3898 (4) | 0.6567 (3) | 0.0652 (9) | |
H20 | 0.5916 | 0.2837 | 0.6619 | 0.078* | |
C21 | 0.6512 (4) | 0.4621 (4) | 0.6324 (3) | 0.0712 (10) | |
H21 | 0.7588 | 0.4044 | 0.6212 | 0.085* | |
C22 | 0.5955 (4) | 0.6178 (4) | 0.6242 (3) | 0.0732 (10) | |
H22 | 0.6641 | 0.6664 | 0.6080 | 0.088* | |
C23 | 0.4364 (4) | 0.7008 (4) | 0.6404 (3) | 0.0694 (10) | |
H23 | 0.3968 | 0.8068 | 0.6352 | 0.083* | |
C24 | 0.3349 (4) | 0.6297 (4) | 0.6642 (3) | 0.0613 (9) | |
H24 | 0.2272 | 0.6885 | 0.6741 | 0.074* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0796 (15) | 0.0911 (17) | 0.0796 (15) | −0.0621 (14) | 0.0330 (13) | −0.0591 (13) |
C1 | 0.0549 (19) | 0.056 (2) | 0.0551 (18) | −0.0292 (17) | 0.0131 (16) | −0.0327 (15) |
C2 | 0.0539 (18) | 0.053 (2) | 0.063 (2) | −0.0345 (17) | 0.0136 (17) | −0.0325 (16) |
C3 | 0.0472 (17) | 0.0459 (18) | 0.0536 (18) | −0.0257 (16) | 0.0092 (15) | −0.0259 (15) |
C4 | 0.0462 (19) | 0.0422 (18) | 0.055 (2) | −0.0223 (16) | 0.0085 (16) | −0.0260 (15) |
C5 | 0.054 (2) | 0.061 (2) | 0.0596 (19) | −0.0315 (18) | 0.0094 (17) | −0.0312 (17) |
C6 | 0.0497 (19) | 0.071 (2) | 0.074 (2) | −0.0366 (18) | 0.0189 (19) | −0.0404 (19) |
C7 | 0.067 (2) | 0.083 (3) | 0.062 (2) | −0.044 (2) | 0.024 (2) | −0.0392 (19) |
C8 | 0.074 (2) | 0.077 (3) | 0.0506 (19) | −0.041 (2) | 0.0134 (19) | −0.0276 (17) |
C9 | 0.0511 (19) | 0.061 (2) | 0.056 (2) | −0.0263 (17) | 0.0037 (17) | −0.0258 (16) |
O2 | 0.0919 (18) | 0.109 (2) | 0.0926 (17) | −0.0676 (16) | 0.0354 (14) | −0.0717 (16) |
C10 | 0.060 (2) | 0.060 (2) | 0.057 (2) | −0.0297 (18) | 0.0007 (17) | −0.0279 (18) |
C11 | 0.0503 (19) | 0.058 (2) | 0.0533 (18) | −0.0257 (17) | 0.0020 (16) | −0.0258 (17) |
C12 | 0.074 (2) | 0.062 (2) | 0.075 (2) | −0.034 (2) | 0.014 (2) | −0.0324 (19) |
C13 | 0.077 (3) | 0.080 (3) | 0.082 (2) | −0.030 (2) | 0.025 (2) | −0.048 (2) |
C14 | 0.066 (2) | 0.095 (3) | 0.078 (3) | −0.038 (2) | 0.022 (2) | −0.035 (2) |
C15 | 0.080 (3) | 0.093 (3) | 0.090 (3) | −0.056 (2) | 0.026 (2) | −0.041 (2) |
C16 | 0.073 (2) | 0.074 (3) | 0.078 (2) | −0.044 (2) | 0.016 (2) | −0.040 (2) |
C17 | 0.071 (2) | 0.062 (2) | 0.062 (2) | −0.038 (2) | 0.0114 (18) | −0.0319 (19) |
C18 | 0.063 (2) | 0.054 (2) | 0.062 (2) | −0.0300 (19) | 0.0085 (18) | −0.0250 (17) |
C19 | 0.058 (2) | 0.053 (2) | 0.0529 (19) | −0.0280 (18) | 0.0062 (16) | −0.0222 (17) |
C20 | 0.061 (2) | 0.061 (2) | 0.077 (2) | −0.028 (2) | 0.0058 (19) | −0.0280 (19) |
C21 | 0.058 (2) | 0.075 (3) | 0.079 (2) | −0.030 (2) | −0.0004 (19) | −0.026 (2) |
C22 | 0.078 (3) | 0.087 (3) | 0.068 (2) | −0.055 (2) | 0.003 (2) | −0.021 (2) |
C23 | 0.082 (3) | 0.062 (2) | 0.076 (2) | −0.040 (2) | 0.002 (2) | −0.0267 (19) |
C24 | 0.064 (2) | 0.062 (2) | 0.069 (2) | −0.034 (2) | 0.0101 (18) | −0.0299 (18) |
Geometric parameters (Å, º) top
O1—C2 | 1.380 (3) | C12—C13 | 1.380 (4) |
O1—H1O1 | 0.8200 | C12—H12 | 0.9300 |
C1—C2 | 1.387 (3) | C13—C14 | 1.369 (4) |
C1—C3i | 1.393 (3) | C13—H13 | 0.9300 |
C1—H1 | 0.9300 | C14—C15 | 1.363 (4) |
C2—C3 | 1.400 (4) | C14—H14 | 0.9300 |
C3—C1i | 1.393 (3) | C15—C16 | 1.371 (4) |
C3—C4 | 1.493 (3) | C15—H15 | 0.9300 |
C4—C9 | 1.383 (4) | C16—H16 | 0.9300 |
C4—C5 | 1.397 (4) | C17—C18 | 1.322 (4) |
C5—C6 | 1.389 (3) | C17—H17 | 0.90 (3) |
C5—H5 | 0.9300 | C18—C19 | 1.450 (4) |
C6—C7 | 1.362 (4) | C18—H18 | 0.9300 |
C6—H6 | 0.9300 | C19—C20 | 1.384 (4) |
C7—C8 | 1.360 (4) | C19—C24 | 1.385 (4) |
C7—H7 | 0.9300 | C20—C21 | 1.369 (4) |
C8—C9 | 1.379 (3) | C20—H20 | 0.9300 |
C8—H8 | 0.9300 | C21—C22 | 1.368 (4) |
C9—H9 | 0.9300 | C21—H21 | 0.9300 |
O2—C10 | 1.234 (3) | C22—C23 | 1.372 (4) |
C10—C17 | 1.459 (4) | C22—H22 | 0.9300 |
C10—C11 | 1.486 (4) | C23—C24 | 1.372 (4) |
C11—C12 | 1.381 (4) | C23—H23 | 0.9300 |
C11—C16 | 1.382 (4) | C24—H24 | 0.9300 |
| | | |
C2—O1—H1O1 | 109.5 | C14—C13—C12 | 120.1 (3) |
C2—C1—C3i | 123.1 (3) | C14—C13—H13 | 120.0 |
C2—C1—H1 | 118.5 | C12—C13—H13 | 120.0 |
C3i—C1—H1 | 118.5 | C15—C14—C13 | 119.8 (3) |
O1—C2—C1 | 121.5 (3) | C15—C14—H14 | 120.1 |
O1—C2—C3 | 118.5 (2) | C13—C14—H14 | 120.1 |
C1—C2—C3 | 120.0 (2) | C14—C15—C16 | 120.4 (3) |
C1i—C3—C2 | 116.9 (2) | C14—C15—H15 | 119.8 |
C1i—C3—C4 | 119.2 (2) | C16—C15—H15 | 119.8 |
C2—C3—C4 | 123.8 (2) | C15—C16—C11 | 121.1 (3) |
C9—C4—C5 | 118.0 (2) | C15—C16—H16 | 119.5 |
C9—C4—C3 | 120.0 (3) | C11—C16—H16 | 119.5 |
C5—C4—C3 | 121.9 (3) | C18—C17—C10 | 122.1 (3) |
C6—C5—C4 | 120.2 (3) | C18—C17—H17 | 118.0 (18) |
C6—C5—H5 | 119.9 | C10—C17—H17 | 118.9 (18) |
C4—C5—H5 | 119.9 | C17—C18—C19 | 129.0 (3) |
C7—C6—C5 | 120.5 (3) | C17—C18—H18 | 115.5 |
C7—C6—H6 | 119.7 | C19—C18—H18 | 115.5 |
C5—C6—H6 | 119.7 | C20—C19—C24 | 117.3 (3) |
C8—C7—C6 | 119.5 (3) | C20—C19—C18 | 119.6 (3) |
C8—C7—H7 | 120.2 | C24—C19—C18 | 123.0 (3) |
C6—C7—H7 | 120.2 | C21—C20—C19 | 121.2 (3) |
C7—C8—C9 | 121.2 (3) | C21—C20—H20 | 119.4 |
C7—C8—H8 | 119.4 | C19—C20—H20 | 119.4 |
C9—C8—H8 | 119.4 | C22—C21—C20 | 121.0 (3) |
C8—C9—C4 | 120.5 (3) | C22—C21—H21 | 119.5 |
C8—C9—H9 | 119.8 | C20—C21—H21 | 119.5 |
C4—C9—H9 | 119.8 | C21—C22—C23 | 118.6 (3) |
O2—C10—C17 | 120.0 (3) | C21—C22—H22 | 120.7 |
O2—C10—C11 | 119.1 (3) | C23—C22—H22 | 120.7 |
C17—C10—C11 | 120.7 (3) | C22—C23—C24 | 120.9 (3) |
C12—C11—C16 | 117.9 (3) | C22—C23—H23 | 119.6 |
C12—C11—C10 | 123.8 (3) | C24—C23—H23 | 119.6 |
C16—C11—C10 | 118.3 (3) | C23—C24—C19 | 121.0 (3) |
C13—C12—C11 | 120.9 (3) | C23—C24—H24 | 119.5 |
C13—C12—H12 | 119.6 | C19—C24—H24 | 119.5 |
C11—C12—H12 | 119.6 | | |
| | | |
C3i—C1—C2—O1 | 178.9 (3) | C16—C11—C12—C13 | −0.7 (5) |
C3i—C1—C2—C3 | 0.3 (5) | C10—C11—C12—C13 | −179.2 (3) |
O1—C2—C3—C1i | −178.9 (3) | C11—C12—C13—C14 | 0.5 (5) |
C1—C2—C3—C1i | −0.3 (5) | C12—C13—C14—C15 | 0.2 (6) |
O1—C2—C3—C4 | 1.1 (4) | C13—C14—C15—C16 | −0.7 (6) |
C1—C2—C3—C4 | 179.7 (3) | C14—C15—C16—C11 | 0.5 (5) |
C1i—C3—C4—C9 | 38.3 (4) | C12—C11—C16—C15 | 0.2 (5) |
C2—C3—C4—C9 | −141.6 (3) | C10—C11—C16—C15 | 178.8 (3) |
C1i—C3—C4—C5 | −137.6 (3) | O2—C10—C17—C18 | −22.4 (5) |
C2—C3—C4—C5 | 42.4 (4) | O2—C10—C17—C18 | −22.4 (5) |
C9—C4—C5—C6 | −0.8 (4) | C11—C10—C17—C18 | 153.3 (3) |
C3—C4—C5—C6 | 175.2 (3) | C10—C17—C18—C19 | −175.4 (3) |
C4—C5—C6—C7 | 0.1 (4) | C17—C18—C19—C20 | 165.9 (3) |
C5—C6—C7—C8 | 0.4 (5) | C17—C18—C19—C24 | −15.2 (5) |
C6—C7—C8—C9 | −0.3 (5) | C24—C19—C20—C21 | 0.4 (5) |
C7—C8—C9—C4 | −0.4 (5) | C18—C19—C20—C21 | 179.4 (3) |
C5—C4—C9—C8 | 1.0 (4) | C19—C20—C21—C22 | 0.1 (5) |
C3—C4—C9—C8 | −175.2 (3) | C20—C21—C22—C23 | −0.3 (5) |
O2—C10—C11—C12 | −170.1 (3) | C21—C22—C23—C24 | 0.0 (5) |
C17—C10—C11—C12 | 14.0 (5) | C22—C23—C24—C19 | 0.6 (5) |
O2—C10—C11—C16 | 11.4 (5) | C20—C19—C24—C23 | −0.7 (5) |
C17—C10—C11—C16 | −164.5 (3) | C18—C19—C24—C23 | −179.7 (3) |
Symmetry code: (i) −x, −y, −z+1. |
(Ic) 2,5-diphenylhydroquinone–1-(4-methoxyphenyl)-3-phenyl-2-propen-1-one (1/2)
top
Crystal data top
C18H14O2·2C16H14O2 | Z = 2 |
Mr = 738.84 | F(000) = 780 |
Triclinic, P1 | Dx = 1.241 Mg m−3 |
a = 10.322 (2) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 11.051 (2) Å | Cell parameters from 6451 reflections |
c = 18.041 (3) Å | θ = 1.0–25.4° |
α = 83.11 (2)° | µ = 0.08 mm−1 |
β = 75.54 (2)° | T = 293 K |
γ = 89.70 (2)° | Prism, yellow |
V = 1977.6 (7) Å3 | 0.2 × 0.1 × 0.08 mm |
Data collection top
Nonius KappaCCD diffractometer | 2911 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.000 |
Graphite monochromator | θmax = 25.4°, θmin = 1.2° |
Detector resolution: 95 pixels mm-1 | h = 0→12 |
ϕ scan | k = −13→13 |
6990 measured reflections | l = −20→21 |
6990 independent reflections | |
Refinement top
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)] = 0.068 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.224 | H-atom parameters constrained |
S = 0.85 | w = 1/[σ2(Fo2) + (0.1252P)2] where P = (Fo2 + 2Fc2)/3 |
6990 reflections | (Δ/σ)max = 0.001 |
506 parameters | Δρmax = 0.14 e Å−3 |
0 restraints | Δρmin = −0.14 e Å−3 |
Crystal data top
C18H14O2·2C16H14O2 | γ = 89.70 (2)° |
Mr = 738.84 | V = 1977.6 (7) Å3 |
Triclinic, P1 | Z = 2 |
a = 10.322 (2) Å | Mo Kα radiation |
b = 11.051 (2) Å | µ = 0.08 mm−1 |
c = 18.041 (3) Å | T = 293 K |
α = 83.11 (2)° | 0.2 × 0.1 × 0.08 mm |
β = 75.54 (2)° | |
Data collection top
Nonius KappaCCD diffractometer | 2911 reflections with I > 2σ(I) |
6990 measured reflections | Rint = 0.000 |
6990 independent reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.068 | 0 restraints |
wR(F2) = 0.224 | H-atom parameters constrained |
S = 0.85 | Δρmax = 0.14 e Å−3 |
6990 reflections | Δρmin = −0.14 e Å−3 |
506 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 | x | y | z | Uiso*/Ueq | |
O1A | 0.7717 (3) | 0.4742 (3) | −0.05826 (18) | 0.0772 (8) | |
H1OA | 0.7854 | 0.4108 | −0.0781 | 0.12 (2)* | |
C1A | 0.5444 (4) | 0.4389 (3) | −0.0625 (2) | 0.0634 (11) | |
H1A | 0.5759 | 0.3981 | −0.1054 | 0.076* | |
C2A | 0.6359 (4) | 0.4849 (3) | −0.0282 (2) | 0.0609 (10) | |
C3A | 0.5924 (4) | 0.5490 (3) | 0.0354 (2) | 0.0589 (10) | |
C4A | 0.6831 (4) | 0.6002 (4) | 0.0758 (2) | 0.0640 (11) | |
C5A | 0.7932 (4) | 0.5370 (4) | 0.0915 (2) | 0.0739 (12) | |
H5A | 0.8120 | 0.4612 | 0.0745 | 0.089* | |
C6A | 0.8744 (5) | 0.5846 (5) | 0.1316 (3) | 0.0885 (14) | |
H6A | 0.9470 | 0.5411 | 0.1413 | 0.106* | |
C7A | 0.8479 (6) | 0.6960 (6) | 0.1572 (3) | 0.1004 (18) | |
H7A | 0.9034 | 0.7288 | 0.1835 | 0.120* | |
C8A | 0.7383 (6) | 0.7600 (5) | 0.1438 (3) | 0.0940 (16) | |
H8A | 0.7189 | 0.8346 | 0.1624 | 0.113* | |
C9A | 0.6584 (5) | 0.7130 (4) | 0.1029 (3) | 0.0782 (13) | |
H9A | 0.5865 | 0.7575 | 0.0931 | 0.094* | |
O1B | 0.2720 (3) | −0.0280 (2) | 0.44902 (17) | 0.0765 (8) | |
H1OB | 0.2707 | −0.0951 | 0.4342 | 0.092* | |
C1B | 0.5038 (4) | −0.0657 (3) | 0.4402 (2) | 0.0611 (10) | |
H1B | 0.5053 | −0.1099 | 0.3992 | 0.073* | |
C2B | 0.3849 (4) | −0.0156 (3) | 0.4756 (2) | 0.0581 (10) | |
C3B | 0.3787 (4) | 0.0527 (3) | 0.5367 (2) | 0.0590 (10) | |
C4B | 0.2537 (4) | 0.1082 (3) | 0.5784 (2) | 0.0615 (11) | |
C5B | 0.1282 (4) | 0.0520 (4) | 0.5921 (2) | 0.0705 (12) | |
H5B | 0.1200 | −0.0214 | 0.5730 | 0.085* | |
C6B | 0.0150 (5) | 0.1043 (4) | 0.6339 (3) | 0.0792 (13) | |
H6B | −0.0680 | 0.0648 | 0.6440 | 0.095* | |
C7B | 0.0254 (5) | 0.2153 (5) | 0.6606 (3) | 0.0865 (15) | |
H7B | −0.0503 | 0.2516 | 0.6877 | 0.104* | |
C8B | 0.1493 (5) | 0.2708 (4) | 0.6463 (3) | 0.0797 (13) | |
H8B | 0.1570 | 0.3452 | 0.6643 | 0.096* | |
C9B | 0.2610 (4) | 0.2190 (4) | 0.6063 (2) | 0.0657 (11) | |
H9B | 0.3437 | 0.2586 | 0.5975 | 0.079* | |
O2A | 0.2008 (3) | 0.7358 (3) | 0.13229 (17) | 0.0786 (9) | |
O3A | 0.5437 (3) | 1.1547 (3) | 0.20548 (19) | 0.0946 (10) | |
C10A | 0.2301 (4) | 0.8390 (4) | 0.0953 (3) | 0.0682 (11) | |
C11A | 0.3118 (4) | 0.9254 (3) | 0.1228 (2) | 0.0621 (11) | |
C12A | 0.3604 (5) | 1.0349 (4) | 0.0800 (3) | 0.0862 (14) | |
H12A | 0.3404 | 1.0559 | 0.0327 | 0.103* | |
C13A | 0.4386 (5) | 1.1151 (4) | 0.1056 (3) | 0.0784 (13) | |
H13A | 0.4701 | 1.1886 | 0.0759 | 0.094* | |
C14A | 0.4679 (4) | 1.0842 (4) | 0.1745 (3) | 0.0716 (12) | |
C15A | 0.4203 (5) | 0.9761 (4) | 0.2192 (3) | 0.0874 (14) | |
H15A | 0.4396 | 0.9561 | 0.2668 | 0.105* | |
C16A | 0.3434 (5) | 0.8975 (4) | 0.1925 (3) | 0.0802 (13) | |
H16A | 0.3123 | 0.8239 | 0.2223 | 0.096* | |
C17A | 0.5992 (5) | 1.2648 (4) | 0.1614 (3) | 0.0965 (16) | |
H17C | 0.6498 | 1.3048 | 0.1896 | 0.116* | |
H17D | 0.5280 | 1.3160 | 0.1523 | 0.116* | |
H17E | 0.6566 | 1.2492 | 0.1131 | 0.116* | |
C18A | 0.1828 (5) | 0.8735 (4) | 0.0265 (3) | 0.0812 (13) | |
H18A | 0.2080 | 0.9502 | −0.0007 | 0.097* | |
C19A | 0.1065 (4) | 0.8033 (4) | 0.0003 (2) | 0.0702 (12) | |
H19A | 0.0821 | 0.7279 | 0.0295 | 0.084* | |
C20A | 0.0550 (4) | 0.8268 (4) | −0.0679 (3) | 0.0668 (11) | |
C21A | −0.0264 (5) | 0.7426 (4) | −0.0828 (3) | 0.0828 (14) | |
H21A | −0.0496 | 0.6715 | −0.0487 | 0.099* | |
C22A | −0.0766 (5) | 0.7603 (5) | −0.1489 (3) | 0.0979 (15) | |
H22A | −0.1336 | 0.7025 | −0.1584 | 0.118* | |
C23A | −0.0395 (5) | 0.8647 (5) | −0.1987 (3) | 0.0918 (15) | |
H23A | −0.0698 | 0.8771 | −0.2434 | 0.110* | |
C24A | 0.0394 (6) | 0.9490 (5) | −0.1841 (3) | 0.1105 (19) | |
H24A | 0.0630 | 1.0197 | −0.2185 | 0.133* | |
C25A | 0.0862 (6) | 0.9326 (4) | −0.1187 (3) | 0.0948 (16) | |
H25A | 0.1393 | 0.9932 | −0.1086 | 0.114* | |
O2B | 0.2828 (3) | 0.7556 (2) | 0.38952 (16) | 0.0749 (8) | |
O3B | 0.6991 (3) | 0.3462 (3) | 0.31561 (17) | 0.0835 (9) | |
C10B | 0.2777 (4) | 0.6524 (4) | 0.4267 (2) | 0.0634 (11) | |
C11B | 0.3851 (4) | 0.5662 (3) | 0.4002 (2) | 0.0570 (10) | |
C12B | 0.3952 (4) | 0.4527 (3) | 0.4393 (2) | 0.0698 (12) | |
H12B | 0.3302 | 0.4268 | 0.4842 | 0.084* | |
C13B | 0.4980 (4) | 0.3767 (4) | 0.4140 (2) | 0.0705 (12) | |
H13B | 0.5034 | 0.3014 | 0.4420 | 0.085* | |
C14B | 0.5926 (4) | 0.4130 (4) | 0.3471 (2) | 0.0625 (11) | |
C15B | 0.5831 (4) | 0.5245 (4) | 0.3061 (2) | 0.0742 (12) | |
H15B | 0.6469 | 0.5488 | 0.2603 | 0.089* | |
C16B | 0.4804 (4) | 0.6002 (3) | 0.3321 (2) | 0.0680 (12) | |
H16B | 0.4749 | 0.6751 | 0.3037 | 0.082* | |
C17B | 0.7086 (5) | 0.2247 (4) | 0.3500 (3) | 0.0959 (16) | |
H17F | 0.7879 | 0.1882 | 0.3224 | 0.115* | |
H17G | 0.6315 | 0.1776 | 0.3493 | 0.115* | |
H17H | 0.7126 | 0.2269 | 0.4023 | 0.115* | |
C18B | 0.1710 (4) | 0.6182 (4) | 0.4961 (2) | 0.0729 (12) | |
H18B | 0.1729 | 0.5418 | 0.5237 | 0.087* | |
C19B | 0.0720 (4) | 0.6903 (4) | 0.5217 (2) | 0.0646 (11) | |
H19B | 0.0733 | 0.7657 | 0.4924 | 0.078* | |
C20B | −0.0395 (4) | 0.6671 (4) | 0.5902 (2) | 0.0666 (11) | |
C21B | −0.1371 (4) | 0.7533 (4) | 0.6056 (3) | 0.0755 (13) | |
H21B | −0.1316 | 0.8249 | 0.5720 | 0.091* | |
C22B | −0.2422 (5) | 0.7338 (5) | 0.6702 (3) | 0.0932 (16) | |
H22B | −0.3070 | 0.7926 | 0.6800 | 0.112* | |
C23B | −0.2525 (5) | 0.6296 (6) | 0.7198 (3) | 0.0974 (16) | |
H23B | −0.3240 | 0.6174 | 0.7633 | 0.117* | |
C24B | −0.1576 (5) | 0.5429 (5) | 0.7056 (3) | 0.1015 (17) | |
H24B | −0.1648 | 0.4711 | 0.7392 | 0.122* | |
C25B | −0.0508 (5) | 0.5619 (4) | 0.6411 (3) | 0.0901 (15) | |
H25B | 0.0141 | 0.5031 | 0.6320 | 0.108* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1A | 0.0514 (19) | 0.084 (2) | 0.095 (2) | −0.0050 (15) | −0.0092 (15) | −0.0225 (18) |
C1A | 0.058 (3) | 0.060 (2) | 0.072 (3) | −0.009 (2) | −0.014 (2) | −0.012 (2) |
C2A | 0.049 (3) | 0.060 (2) | 0.068 (3) | −0.006 (2) | −0.006 (2) | −0.005 (2) |
C3A | 0.053 (3) | 0.059 (2) | 0.064 (3) | −0.0117 (19) | −0.013 (2) | −0.007 (2) |
C4A | 0.061 (3) | 0.069 (3) | 0.057 (3) | −0.016 (2) | −0.008 (2) | −0.001 (2) |
C5A | 0.061 (3) | 0.086 (3) | 0.071 (3) | −0.018 (2) | −0.011 (2) | −0.005 (2) |
C6A | 0.061 (3) | 0.128 (4) | 0.073 (3) | −0.028 (3) | −0.015 (3) | −0.006 (3) |
C7A | 0.084 (4) | 0.149 (5) | 0.066 (3) | −0.054 (4) | −0.012 (3) | −0.016 (3) |
C8A | 0.104 (4) | 0.098 (4) | 0.073 (3) | −0.043 (3) | −0.007 (3) | −0.012 (3) |
C9A | 0.083 (3) | 0.077 (3) | 0.073 (3) | −0.022 (2) | −0.015 (3) | −0.009 (2) |
O1B | 0.072 (2) | 0.0742 (18) | 0.098 (2) | 0.0152 (15) | −0.0419 (17) | −0.0276 (16) |
C1B | 0.063 (3) | 0.062 (2) | 0.061 (3) | 0.009 (2) | −0.020 (2) | −0.0090 (19) |
C2B | 0.056 (3) | 0.058 (2) | 0.066 (3) | 0.0055 (19) | −0.028 (2) | −0.006 (2) |
C3B | 0.064 (3) | 0.054 (2) | 0.061 (3) | 0.005 (2) | −0.022 (2) | −0.0014 (19) |
C4B | 0.062 (3) | 0.065 (3) | 0.056 (3) | 0.008 (2) | −0.018 (2) | 0.003 (2) |
C5B | 0.066 (3) | 0.074 (3) | 0.072 (3) | 0.011 (2) | −0.020 (2) | −0.004 (2) |
C6B | 0.064 (3) | 0.098 (4) | 0.072 (3) | 0.010 (3) | −0.019 (2) | 0.007 (3) |
C7B | 0.077 (4) | 0.106 (4) | 0.076 (3) | 0.029 (3) | −0.021 (3) | −0.009 (3) |
C8B | 0.086 (4) | 0.080 (3) | 0.074 (3) | 0.022 (3) | −0.021 (3) | −0.013 (2) |
C9B | 0.062 (3) | 0.069 (3) | 0.066 (3) | 0.009 (2) | −0.016 (2) | −0.011 (2) |
O2A | 0.089 (2) | 0.0706 (18) | 0.075 (2) | −0.0088 (16) | −0.0203 (17) | −0.0022 (16) |
O3A | 0.107 (3) | 0.093 (2) | 0.087 (2) | −0.029 (2) | −0.029 (2) | −0.0121 (19) |
C10A | 0.067 (3) | 0.069 (3) | 0.064 (3) | 0.005 (2) | −0.008 (2) | −0.006 (2) |
C11A | 0.066 (3) | 0.055 (2) | 0.062 (3) | −0.004 (2) | −0.011 (2) | −0.005 (2) |
C12A | 0.095 (4) | 0.097 (3) | 0.067 (3) | −0.019 (3) | −0.026 (3) | 0.004 (3) |
C13A | 0.083 (3) | 0.084 (3) | 0.067 (3) | −0.023 (3) | −0.023 (3) | 0.009 (2) |
C14A | 0.069 (3) | 0.080 (3) | 0.068 (3) | −0.003 (2) | −0.018 (2) | −0.017 (3) |
C15A | 0.117 (4) | 0.077 (3) | 0.075 (3) | −0.007 (3) | −0.039 (3) | −0.004 (3) |
C16A | 0.098 (4) | 0.074 (3) | 0.067 (3) | −0.008 (3) | −0.022 (3) | −0.002 (2) |
C17A | 0.090 (4) | 0.101 (4) | 0.095 (4) | −0.020 (3) | −0.008 (3) | −0.030 (3) |
C18A | 0.093 (4) | 0.077 (3) | 0.074 (3) | −0.009 (3) | −0.026 (3) | −0.001 (2) |
C19A | 0.065 (3) | 0.077 (3) | 0.063 (3) | 0.000 (2) | −0.011 (2) | −0.001 (2) |
C20A | 0.061 (3) | 0.064 (3) | 0.074 (3) | −0.001 (2) | −0.013 (2) | −0.008 (2) |
C21A | 0.081 (3) | 0.087 (3) | 0.076 (3) | −0.016 (3) | −0.019 (3) | 0.007 (3) |
C22A | 0.087 (4) | 0.107 (4) | 0.102 (4) | −0.019 (3) | −0.031 (3) | −0.007 (3) |
C23A | 0.096 (4) | 0.103 (4) | 0.081 (4) | 0.000 (3) | −0.035 (3) | −0.003 (3) |
C24A | 0.155 (6) | 0.089 (4) | 0.098 (4) | −0.025 (4) | −0.064 (4) | 0.014 (3) |
C25A | 0.134 (5) | 0.075 (3) | 0.084 (4) | −0.021 (3) | −0.050 (3) | 0.007 (3) |
O2B | 0.079 (2) | 0.0635 (17) | 0.075 (2) | 0.0086 (15) | −0.0093 (16) | −0.0009 (15) |
O3B | 0.075 (2) | 0.078 (2) | 0.091 (2) | 0.0177 (17) | −0.0076 (17) | −0.0130 (17) |
C10B | 0.067 (3) | 0.063 (3) | 0.062 (3) | 0.003 (2) | −0.021 (2) | −0.005 (2) |
C11B | 0.060 (3) | 0.053 (2) | 0.056 (2) | −0.0015 (19) | −0.011 (2) | −0.0063 (18) |
C12B | 0.067 (3) | 0.070 (3) | 0.063 (3) | 0.008 (2) | −0.004 (2) | 0.003 (2) |
C13B | 0.074 (3) | 0.064 (3) | 0.064 (3) | 0.009 (2) | −0.008 (2) | 0.009 (2) |
C14B | 0.063 (3) | 0.061 (2) | 0.064 (3) | 0.006 (2) | −0.014 (2) | −0.015 (2) |
C15B | 0.075 (3) | 0.064 (3) | 0.070 (3) | −0.005 (2) | 0.004 (2) | −0.001 (2) |
C16B | 0.073 (3) | 0.051 (2) | 0.073 (3) | −0.001 (2) | −0.005 (2) | −0.004 (2) |
C17B | 0.109 (4) | 0.078 (3) | 0.102 (4) | 0.035 (3) | −0.027 (3) | −0.016 (3) |
C18B | 0.076 (3) | 0.071 (3) | 0.066 (3) | 0.009 (2) | −0.010 (2) | −0.002 (2) |
C19B | 0.062 (3) | 0.070 (3) | 0.063 (3) | 0.006 (2) | −0.017 (2) | −0.009 (2) |
C20B | 0.060 (3) | 0.073 (3) | 0.068 (3) | 0.010 (2) | −0.017 (2) | −0.015 (2) |
C21B | 0.066 (3) | 0.085 (3) | 0.083 (3) | 0.019 (2) | −0.027 (3) | −0.025 (2) |
C22B | 0.062 (3) | 0.123 (4) | 0.097 (4) | 0.024 (3) | −0.012 (3) | −0.041 (4) |
C23B | 0.076 (4) | 0.130 (5) | 0.081 (4) | −0.001 (3) | −0.005 (3) | −0.025 (3) |
C24B | 0.096 (4) | 0.109 (4) | 0.086 (4) | 0.008 (3) | 0.001 (3) | −0.007 (3) |
C25B | 0.082 (4) | 0.089 (3) | 0.086 (4) | 0.020 (3) | 0.000 (3) | −0.004 (3) |
Geometric parameters (Å, º) top
O1A—C2A | 1.380 (4) | C16A—H16A | 0.9300 |
O1A—H1OA | 0.8200 | C17A—H17C | 0.9569 |
C1A—C2A | 1.380 (5) | C17A—H17D | 0.9605 |
C1A—C3Ai | 1.386 (5) | C17A—H17E | 0.9588 |
C1A—H1A | 0.9300 | C18A—C19A | 1.313 (6) |
C2A—C3A | 1.398 (5) | C18A—H18A | 0.9300 |
C3A—C1Ai | 1.386 (5) | C19A—C20A | 1.453 (6) |
C3A—C4A | 1.473 (6) | C19A—H19A | 0.9300 |
C4A—C9A | 1.393 (5) | C20A—C21A | 1.351 (6) |
C4A—C5A | 1.402 (5) | C20A—C25A | 1.382 (6) |
C5A—C6A | 1.379 (6) | C21A—C22A | 1.408 (7) |
C5A—H5A | 0.9300 | C21A—H21A | 0.9300 |
C6A—C7A | 1.368 (7) | C22A—C23A | 1.367 (6) |
C6A—H6A | 0.9300 | C22A—H22A | 0.9300 |
C7A—C8A | 1.387 (7) | C23A—C24A | 1.331 (7) |
C7A—H7A | 0.9300 | C23A—H23A | 0.9300 |
C8A—C9A | 1.377 (6) | C24A—C25A | 1.376 (6) |
C8A—H8A | 0.9300 | C24A—H24A | 0.9300 |
C9A—H9A | 0.9300 | C25A—H25A | 0.9300 |
O1B—C2B | 1.380 (4) | O2B—C10B | 1.247 (4) |
O1B—H1OB | 0.8200 | O3B—C14B | 1.362 (4) |
C1B—C2B | 1.381 (5) | O3B—C17B | 1.423 (5) |
C1B—C3Bii | 1.391 (5) | C10B—C18B | 1.458 (6) |
C1B—H1B | 0.9300 | C10B—C11B | 1.483 (5) |
C2B—C3B | 1.398 (5) | C11B—C12B | 1.380 (5) |
C3B—C1Bii | 1.391 (5) | C11B—C16B | 1.381 (5) |
C3B—C4B | 1.491 (5) | C12B—C13B | 1.371 (5) |
C4B—C9B | 1.388 (5) | C12B—H12B | 0.9300 |
C4B—C5B | 1.392 (5) | C13B—C14B | 1.367 (5) |
C5B—C6B | 1.387 (5) | C13B—H13B | 0.9300 |
C5B—H5B | 0.9300 | C14B—C15B | 1.376 (5) |
C6B—C7B | 1.384 (6) | C15B—C16B | 1.371 (5) |
C6B—H6B | 0.9300 | C15B—H15B | 0.9300 |
C7B—C8B | 1.372 (6) | C16B—H16B | 0.9300 |
C7B—H7B | 0.9300 | C17B—H17F | 0.9593 |
C8B—C9B | 1.363 (5) | C17B—H17G | 0.9575 |
C8B—H8B | 0.9300 | C17B—H17H | 0.9584 |
C9B—H9B | 0.9300 | C18B—C19B | 1.318 (5) |
O2A—C10A | 1.248 (5) | C18B—H18B | 0.9300 |
O3A—C14A | 1.364 (5) | C19B—C20B | 1.461 (6) |
O3A—C17A | 1.409 (5) | C19B—H19B | 0.9300 |
C10A—C18A | 1.454 (6) | C20B—C25B | 1.378 (6) |
C10A—C11A | 1.483 (6) | C20B—C21B | 1.383 (5) |
C11A—C16A | 1.376 (6) | C21B—C22B | 1.376 (6) |
C11A—C12A | 1.379 (5) | C21B—H21B | 0.9300 |
C12A—C13A | 1.393 (6) | C22B—C23B | 1.358 (7) |
C12A—H12A | 0.9300 | C22B—H22B | 0.9300 |
C13A—C14A | 1.356 (6) | C23B—C24B | 1.367 (6) |
C13A—H13A | 0.9300 | C23B—H23B | 0.9300 |
C14A—C15A | 1.378 (6) | C24B—C25B | 1.384 (6) |
C15A—C16A | 1.385 (6) | C24B—H24B | 0.9300 |
C15A—H15A | 0.9300 | C25B—H25B | 0.9300 |
| | | |
C2A—O1A—H1OA | 109.5 | H17C—C17A—H17D | 109.5 |
C2A—C1A—C3Ai | 122.6 (4) | O3A—C17A—H17E | 110.5 |
C2A—C1A—H1A | 118.7 | H17C—C17A—H17E | 109.4 |
C3Ai—C1A—H1A | 118.7 | H17D—C17A—H17E | 109.4 |
C1A—C2A—O1A | 120.8 (4) | C19A—C18A—C10A | 124.1 (4) |
C1A—C2A—C3A | 120.3 (4) | C19A—C18A—H18A | 117.9 |
O1A—C2A—C3A | 118.8 (4) | C10A—C18A—H18A | 117.9 |
C1Ai—C3A—C2A | 117.1 (4) | C18A—C19A—C20A | 129.1 (4) |
C1Ai—C3A—C4A | 119.1 (4) | C18A—C19A—H19A | 115.5 |
C2A—C3A—C4A | 123.8 (4) | C20A—C19A—H19A | 115.5 |
C9A—C4A—C5A | 117.2 (4) | C21A—C20A—C25A | 118.3 (5) |
C9A—C4A—C3A | 120.4 (4) | C21A—C20A—C19A | 119.2 (4) |
C5A—C4A—C3A | 122.4 (4) | C25A—C20A—C19A | 122.5 (4) |
C6A—C5A—C4A | 121.6 (5) | C20A—C21A—C22A | 121.3 (4) |
C6A—C5A—H5A | 119.2 | C20A—C21A—H21A | 119.4 |
C4A—C5A—H5A | 119.2 | C22A—C21A—H21A | 119.4 |
C7A—C6A—C5A | 119.9 (5) | C23A—C22A—C21A | 118.3 (5) |
C7A—C6A—H6A | 120.1 | C23A—C22A—H22A | 120.8 |
C5A—C6A—H6A | 120.1 | C21A—C22A—H22A | 120.8 |
C6A—C7A—C8A | 120.0 (5) | C24A—C23A—C22A | 120.9 (5) |
C6A—C7A—H7A | 120.0 | C24A—C23A—H23A | 119.5 |
C8A—C7A—H7A | 120.0 | C22A—C23A—H23A | 119.5 |
C9A—C8A—C7A | 120.0 (5) | C23A—C24A—C25A | 120.7 (5) |
C9A—C8A—H8A | 120.0 | C23A—C24A—H24A | 119.7 |
C7A—C8A—H8A | 120.0 | C25A—C24A—H24A | 119.7 |
C8A—C9A—C4A | 121.3 (5) | C24A—C25A—C20A | 120.5 (5) |
C8A—C9A—H9A | 119.3 | C24A—C25A—H25A | 119.8 |
C4A—C9A—H9A | 119.3 | C20A—C25A—H25A | 119.8 |
C2B—O1B—H1OB | 109.5 | C14B—O3B—C17B | 118.7 (3) |
C2B—C1B—C3Bii | 122.6 (4) | O2B—C10B—C18B | 120.9 (4) |
C2B—C1B—H1B | 118.7 | O2B—C10B—C11B | 118.5 (4) |
C3Bii—C1B—H1B | 118.7 | C18B—C10B—C11B | 120.6 (3) |
O1B—C2B—C1B | 120.4 (4) | C12B—C11B—C16B | 117.6 (3) |
O1B—C2B—C3B | 119.1 (3) | C12B—C11B—C10B | 123.8 (4) |
C1B—C2B—C3B | 120.5 (4) | C16B—C11B—C10B | 118.6 (3) |
C1Bii—C3B—C2B | 116.9 (3) | C13B—C12B—C11B | 122.1 (4) |
C1Bii—C3B—C4B | 119.6 (4) | C13B—C12B—H12B | 118.9 |
C2B—C3B—C4B | 123.5 (4) | C11B—C12B—H12B | 118.9 |
C9B—C4B—C5B | 117.8 (4) | C14B—C13B—C12B | 119.3 (4) |
C9B—C4B—C3B | 119.6 (4) | C14B—C13B—H13B | 120.3 |
C5B—C4B—C3B | 122.6 (4) | C12B—C13B—H13B | 120.3 |
C6B—C5B—C4B | 120.7 (4) | O3B—C14B—C13B | 125.1 (4) |
C6B—C5B—H5B | 119.7 | O3B—C14B—C15B | 115.2 (4) |
C4B—C5B—H5B | 119.7 | C13B—C14B—C15B | 119.7 (4) |
C7B—C6B—C5B | 120.1 (5) | C16B—C15B—C14B | 120.5 (4) |
C7B—C6B—H6B | 119.9 | C16B—C15B—H15B | 119.7 |
C5B—C6B—H6B | 119.9 | C14B—C15B—H15B | 119.7 |
C8B—C7B—C6B | 118.9 (4) | C15B—C16B—C11B | 120.7 (4) |
C8B—C7B—H7B | 120.5 | C15B—C16B—H16B | 119.7 |
C6B—C7B—H7B | 120.5 | C11B—C16B—H16B | 119.7 |
C9B—C8B—C7B | 121.2 (5) | O3B—C17B—H17F | 110.2 |
C9B—C8B—H8B | 119.4 | O3B—C17B—H17G | 109.6 |
C7B—C8B—H8B | 119.4 | H17F—C17B—H17G | 109.6 |
C8B—C9B—C4B | 121.2 (4) | O3B—C17B—H17H | 108.7 |
C8B—C9B—H9B | 119.4 | H17F—C17B—H17H | 109.4 |
C4B—C9B—H9B | 119.4 | H17G—C17B—H17H | 109.4 |
C14A—O3A—C17A | 117.6 (4) | C19B—C18B—C10B | 123.2 (4) |
O2A—C10A—C18A | 119.8 (4) | C19B—C18B—H18B | 118.4 |
O2A—C10A—C11A | 119.3 (4) | C10B—C18B—H18B | 118.4 |
C18A—C10A—C11A | 120.8 (4) | C18B—C19B—C20B | 128.3 (4) |
C16A—C11A—C12A | 117.4 (4) | C18B—C19B—H19B | 115.8 |
C16A—C11A—C10A | 120.5 (4) | C20B—C19B—H19B | 115.8 |
C12A—C11A—C10A | 122.1 (4) | C25B—C20B—C21B | 118.3 (4) |
C11A—C12A—C13A | 122.0 (4) | C25B—C20B—C19B | 122.2 (4) |
C11A—C12A—H12A | 119.0 | C21B—C20B—C19B | 119.5 (4) |
C13A—C12A—H12A | 119.0 | C22B—C21B—C20B | 120.4 (5) |
C14A—C13A—C12A | 118.9 (4) | C22B—C21B—H21B | 119.8 |
C14A—C13A—H13A | 120.5 | C20B—C21B—H21B | 119.8 |
C12A—C13A—H13A | 120.5 | C23B—C22B—C21B | 120.8 (5) |
C13A—C14A—O3A | 124.4 (4) | C23B—C22B—H22B | 119.6 |
C13A—C14A—C15A | 120.9 (4) | C21B—C22B—H22B | 119.6 |
O3A—C14A—C15A | 114.7 (4) | C22B—C23B—C24B | 119.8 (5) |
C14A—C15A—C16A | 119.1 (4) | C22B—C23B—H23B | 120.1 |
C14A—C15A—H15A | 120.4 | C24B—C23B—H23B | 120.1 |
C16A—C15A—H15A | 120.4 | C23B—C24B—C25B | 119.9 (5) |
C11A—C16A—C15A | 121.7 (4) | C23B—C24B—H24B | 120.0 |
C11A—C16A—H16A | 119.2 | C25B—C24B—H24B | 120.0 |
C15A—C16A—H16A | 119.2 | C20B—C25B—C24B | 120.8 (4) |
O3A—C17A—H17C | 109.0 | C20B—C25B—H25B | 119.6 |
O3A—C17A—H17D | 108.9 | C24B—C25B—H25B | 119.6 |
| | | |
C3Ai—C1A—C2A—O1A | −178.0 (3) | C13A—C14A—C15A—C16A | 1.1 (7) |
C3Ai—C1A—C2A—C3A | −1.4 (6) | O3A—C14A—C15A—C16A | −179.3 (4) |
C1A—C2A—C3A—C1Ai | 1.3 (6) | C12A—C11A—C16A—C15A | 0.4 (7) |
O1A—C2A—C3A—C1Ai | 178.0 (3) | C10A—C11A—C16A—C15A | 179.5 (4) |
C1A—C2A—C3A—C4A | 179.5 (4) | C14A—C15A—C16A—C11A | −0.9 (7) |
O1A—C2A—C3A—C4A | −3.8 (6) | O2A—C10A—C18A—C19A | 1.6 (7) |
C1Ai—C3A—C4A—C9A | −40.4 (5) | C11A—C10A—C18A—C19A | −177.7 (4) |
C2A—C3A—C4A—C9A | 141.5 (4) | C10A—C18A—C19A—C20A | −179.0 (4) |
C1Ai—C3A—C4A—C5A | 136.9 (4) | C18A—C19A—C20A—C21A | −177.7 (5) |
C2A—C3A—C4A—C5A | −41.2 (6) | C18A—C19A—C20A—C25A | 2.4 (7) |
C9A—C4A—C5A—C6A | −0.4 (6) | C25A—C20A—C21A—C22A | 1.1 (7) |
C3A—C4A—C5A—C6A | −177.8 (4) | C19A—C20A—C21A—C22A | −178.7 (4) |
C4A—C5A—C6A—C7A | 0.1 (7) | C20A—C21A—C22A—C23A | 0.9 (7) |
C5A—C6A—C7A—C8A | 1.0 (7) | C21A—C22A—C23A—C24A | −1.7 (8) |
C6A—C7A—C8A—C9A | −1.8 (7) | C22A—C23A—C24A—C25A | 0.4 (9) |
C7A—C8A—C9A—C4A | 1.6 (7) | C23A—C24A—C25A—C20A | 1.7 (9) |
C5A—C4A—C9A—C8A | −0.4 (6) | C21A—C20A—C25A—C24A | −2.4 (7) |
C3A—C4A—C9A—C8A | 177.0 (4) | C19A—C20A—C25A—C24A | 177.5 (5) |
C3Bii—C1B—C2B—O1B | 178.0 (3) | O2B—C10B—C11B—C12B | 175.6 (4) |
C3Bii—C1B—C2B—C3B | 0.7 (6) | C18B—C10B—C11B—C12B | −2.5 (6) |
O1B—C2B—C3B—C1Bii | −178.0 (3) | O2B—C10B—C11B—C16B | −5.1 (6) |
C1B—C2B—C3B—C1Bii | −0.7 (6) | C18B—C10B—C11B—C16B | 176.9 (4) |
O1B—C2B—C3B—C4B | 3.5 (5) | C16B—C11B—C12B—C13B | 2.4 (6) |
C1B—C2B—C3B—C4B | −179.2 (3) | C10B—C11B—C12B—C13B | −178.3 (4) |
C1Bii—C3B—C4B—C9B | 35.6 (5) | C11B—C12B—C13B—C14B | −1.3 (7) |
C2B—C3B—C4B—C9B | −146.0 (4) | C17B—O3B—C14B—C13B | 6.0 (6) |
C1Bii—C3B—C4B—C5B | −143.1 (4) | C17B—O3B—C14B—C15B | −173.5 (4) |
C2B—C3B—C4B—C5B | 35.3 (6) | C12B—C13B—C14B—O3B | −179.8 (4) |
C9B—C4B—C5B—C6B | −1.5 (6) | C12B—C13B—C14B—C15B | −0.2 (7) |
C3B—C4B—C5B—C6B | 177.3 (3) | O3B—C14B—C15B—C16B | −179.8 (4) |
C4B—C5B—C6B—C7B | 1.9 (6) | C13B—C14B—C15B—C16B | 0.7 (7) |
C5B—C6B—C7B—C8B | −1.3 (7) | C14B—C15B—C16B—C11B | 0.4 (7) |
C6B—C7B—C8B—C9B | 0.3 (7) | C12B—C11B—C16B—C15B | −1.9 (6) |
C7B—C8B—C9B—C4B | 0.0 (6) | C10B—C11B—C16B—C15B | 178.8 (4) |
C5B—C4B—C9B—C8B | 0.5 (6) | O2B—C10B—C18B—C19B | 3.0 (7) |
C3B—C4B—C9B—C8B | −178.3 (4) | C11B—C10B—C18B—C19B | −179.0 (4) |
O2A—C10A—C11A—C16A | −6.7 (6) | C10B—C18B—C19B—C20B | −179.6 (4) |
C18A—C10A—C11A—C16A | 172.6 (4) | C18B—C19B—C20B—C25B | 3.3 (7) |
O2A—C10A—C11A—C12A | 172.4 (4) | C18B—C19B—C20B—C21B | −177.3 (4) |
C18A—C10A—C11A—C12A | −8.3 (6) | C25B—C20B—C21B—C22B | 0.1 (7) |
C16A—C11A—C12A—C13A | 0.0 (7) | C19B—C20B—C21B—C22B | −179.3 (4) |
C10A—C11A—C12A—C13A | −179.1 (4) | C20B—C21B—C22B—C23B | −0.3 (8) |
C11A—C12A—C13A—C14A | 0.1 (7) | C21B—C22B—C23B—C24B | 0.0 (8) |
C12A—C13A—C14A—O3A | 179.8 (4) | C22B—C23B—C24B—C25B | 0.6 (8) |
C12A—C13A—C14A—C15A | −0.7 (7) | C21B—C20B—C25B—C24B | 0.5 (7) |
C17A—O3A—C14A—C13A | −2.5 (6) | C19B—C20B—C25B—C24B | 179.8 (5) |
C17A—O3A—C14A—C15A | 177.9 (4) | C23B—C24B—C25B—C20B | −0.8 (8) |
Symmetry codes: (i) −x+1, −y+1, −z; (ii) −x+1, −y, −z+1. |
Experimental details
| (pyr0) | (Ib) | (Ic) |
Crystal data |
Chemical formula | C18H14O2·2C5H5NO | C18H14O2·2C15H12O | C18H14O2·2C16H14O2 |
Mr | 452.49 | 678.78 | 738.84 |
Crystal system, space group | Triclinic, P1 | Triclinic, P1 | Triclinic, P1 |
Temperature (K) | 293 | 293 | 293 |
a, b, c (Å) | 6.510 (1), 8.971 (1), 11.085 (2) | 9.413 (2), 10.042 (2), 11.848 (2) | 10.322 (2), 11.051 (2), 18.041 (3) |
α, β, γ (°) | 70.746 (2), 73.108 (2), 73.807 (2) | 65.74 (2), 81.57 (2), 62.81 (2) | 83.11 (2), 75.54 (2), 89.70 (2) |
V (Å3) | 572.66 (15) | 907.0 (3) | 1977.6 (7) |
Z | 1 | 1 | 2 |
Radiation type | Mo Kα | Mo Kα | Mo Kα |
µ (mm−1) | 0.09 | 0.08 | 0.08 |
Crystal size (mm) | 0.3 × 0.2 × 0.1 | 0.2 × 0.1 × 0.08 | 0.2 × 0.1 × 0.08 |
|
Data collection |
Diffractometer | Nonius KappaCCD diffractometer | Nonius KappaCCD diffractometer | Nonius KappaCCD diffractometer |
Absorption correction | – | – | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 2021, 2021, 1611 | 5064, 3153, 1284 | 6990, 6990, 2911 |
Rint | 0.000 | 0.043 | 0.000 |
(sin θ/λ)max (Å−1) | 0.596 | 0.596 | 0.603 |
|
Refinement |
R[F2 > 2σ(F2)], wR(F2), S | 0.042, 0.126, 1.06 | 0.043, 0.142, 0.86 | 0.068, 0.224, 0.85 |
No. of reflections | 2021 | 3153 | 6990 |
No. of parameters | 165 | 239 | 506 |
H-atom treatment | H-atom parameters constrained | H-atom parameters constrained | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.12, −0.15 | 0.13, −0.18 | 0.14, −0.14 |
Hydrogen-bond geometry (Å, °) in the three title compounds topD—H···A | D—H | H···A | D···A | D—H···A |
Ia | | | | |
O1—H1O1···O2i | 0.82 | 1.86 | 2.603 (2) | 151 |
N1—H1N···O2ii | 0.86 | 2.00 | 2.854 (2) | 171 |
| | | | |
Ib | | | | |
O1—H1O1···O2 | 0.82 | 1.98 | 2.803 (3) | 177 |
| | | | |
Ic | | | | |
O1a—H1Oa···O2aiii | 0.82 | 1.98 | 2.793 (4) | 172 |
O1b—H1Ob···O2biv | 0.82 | 1.91 | 2.727 (4) | 174 |
Symmetry codes: (i) 2 − x, 1 − y, −z; (ii) 1 − x, −y, −z; (iii) 1 − x, 1 − y, −z; (iv) x, y − 1, z. |
Comparison of selected torsion angles (°) topChalcone | | |
| | |
| C11-C10-C17-C18 | C10-C17-C18-C19 |
I-b | 153.3 | 175.3 |
DEGPUA | 171.9 | -179.4 |
BZYACO | -160.5 | 178.7 |
BZYACO01 | 167.8 | 177.8 |
4'-Methoxychalcone | | |
| C11-C10-C18-C19 | C10-C18-C19-C20 |
I-c(A) | -177.6 | -179.0 |
I-c(B) | -179.0 | -179.5 |
KOTSER | 160.4 | 176.4 |
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The crystal structures of the three inclusion compounds (I–a), (I–b) and (I–c) (see scheme below) were studied as part of a comprehensive investigation concerning the ability of guest molecules in inclusion compounds to undergo homogeneous photochemical reactions. Inclusion compound (I–a) crystallizes in space group P-1. The host molecule occupies a crystallographic inversion center and the guest molecule, which is linked to the host via a hydrogen bond, occupies a general position. The host molecules are disordered so that the hydroxy groups occupy two different sites (with occupancies of ca 0.75 and 1/4, respectively) that are related by 180° rotation around the C7···C7(2 − x,1 − y,-z) axis. The hydrogen bond observed in the major structure [Fig. 1; O1···O2 = 2.603 (3) Å] is shorter (see also Table 1) than that observed in the minor structure [Fig. 2; O1a···O2 = 2.973 (3) Å]. The O atom of the pyridone molecule forms a bifurcated hydrogen bond. In addition to the hydrogen bonds between the host and the guest, there are also hydrogen bonds between the guest molecules, involving atom N1 of one molecule and atom O2 of another molecule, thus forming a dimer.
Compound (I–b) crystallizes in space group P-1. The host molecule occupies a crystallographic inversion center and the guest molecule, which is linked to the host via a hydrogen bond, occupies a general position (Fig. 3 and Table 1). The degree of planarity of the benzilideneacetophenone molecule [chalcone, (b)] in (I–b) differs from the conformation in the two polymorphs of pure (b) [Rabinovich, 1970; refcode BZYACO in the Cambridge Structural Database (Allen, 2002); Ohkura et al., 1973; refcode BZYACO01] and from that of (b) in another inclusion compound (Kaftory et al., 1985; refcode DEGPUA). A comparison of the C11—C10—C17—C18 and C10—C17—C18—C19 torsion angles in the above structures is given in Table 2. It can be seen that the C11—C10—C17—C18 torsion angle in (I–b) is the smallest.
Compound (I–c) crystallizes in space group P-1. Two guest molecules (labeled A and B) occupy general positions, while two host molecules (labeled A and B) occupy different crystallographic inversion centers. The guest molecules are linked to the host molecules via hydrogen bonds (see Table 1). The A and B host–guest couples are packed orthogonally to one another, as can be seen in Fig. 4. The geometry of 4'-methoxychalcone, (c), in (I–c) is similar to the geometry of pure (c) (Li et al., 1992; refcode KOTSER). The molecule of (c) in (I–c) is almost planar. A comparison of the torsion angles is given in Table 2.
In each compound, ? the conformation of the host molecule can be defined by two dihedral angles around the single bonds. However, since the molecule occupies a crystallographic inversion center in all known compounds that include 2,5-diphenylhydroquinone (the present work; Kaftory et al., 1985; refcode DEGREI), the conformation is described by only one dihedral angle. The dihedral angles between the two phenyl rings are 13.9 (1)° for the host molecule in (I–a), 20.1 (1)° for the host molecule in (I–b), and 7.0 (2) and 58.8 (1)° for the two host molecules in the asymmetric unit of (I–c). The dihedral angle between these planes in the inclusion compound with dibenzylideneacetone (DEGREI; Kaftory et al., 1985) is 24.3 (2)°. The distances between potentially photoreactive centers are too long to enable photodimerization in the solid state. The shortest distance between two potentially reactive atoms of the guest molecules that are related by an inversion center [C11—C14(-x,-y,1 − z)] in (I–a) is 5.691 (3) Å, and that in (I–b) is 6.201 (4) Å [C17—C18(-x,1 − y,1 − z)]. The distances between potentially reacting atoms in guest molecules A [C18—C19(-x,-y,-z)] and B [C18—C19(-x,1 − y,1 − z)] in (I–c) are 4.701 (6) and 4.333 (6) Å, respectively. These distances are larger than the limit set for potential photochemical reactions (Cohen & Schmidt, 1964). The relationship? between the two guest molecules in (I–c) is shown in Fig. 5.