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Acta Cryst. (2008). E64, o2248    [ doi:10.1107/S1600536808035113 ]

Biphenyl-2,2'-diyl diacetate

C.-H. Hu, J. Chen, J.-C. Quan and J.-T. Wang

Abstract top

In the title compound, C16H14O4, a derivative of 2,2'-biphenol, the benzene rings are oriented at a dihedral angle of 58.32 (3)°.

Comment top

Some derivatives of andrographolide are important chemical materials. We report herein the crystal structure of the title compound.

In the title compound (Fig. 1), the bond lengths (Allen et al., 1987) and angles are within normal ranges. Rings A (C3-C8) and B (C9-C14) are, of course, planar and the dihedral angle between them is A/B = 58.32 (3)°.

Related literature top

For bond-length data, see: Allen et al. (1987).

Experimental top

For the preparation of the title compound, 2,2'-biphenol (10 g) was dissolved in acetic anhydride (50 ml) at room temperature. After the reaction completed, it was extracted with ethyl acetate, washed with saturated salt water and dryed with sodium sulfate. The product was filtrated, and the organic layer was concentrated. Crystals suitable for X-ray analysis were obtained from ethyl acetate (10 ml) at room temperature.

Refinement top

H atoms were positioned geometrically, with C-H = 0.93 and 0.96 Å for aromatic and methyl H, respectively, and constrained to ride on their parent atoms with Uiso(H) = xUeq(C), where x = 1.5 for methyl H and x = 1.2 for aromatic H atoms.

Computing details top

Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CAD-4 Software (Enraf–Nonius, 1989); data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title molecule, with the atom-numbering scheme. Displacement ellipsoids drawn at the 30% probability level.
Biphenyl-2,2'-diyl diacetate top
Crystal data top
C16H14O4F(000) = 568
Mr = 270.27Dx = 1.315 Mg m−3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 25 reflections
a = 8.8380 (18) Åθ = 9–14°
b = 18.204 (4) ŵ = 0.10 mm−1
c = 8.9620 (18) ÅT = 294 K
β = 108.75 (3)°Block, colorless
V = 1365.3 (5) Å30.30 × 0.20 × 0.10 mm
Z = 4
Data collection top
Enraf–Nonius CAD-4
diffractometer		1645 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.026
graphiteθmax = 25.3°, θmin = 2.2°
ω/2θ scansh = 0→10
Absorption correction: ψ scan
(North et al., 1968)		k = 0→21
Tmin = 0.972, Tmax = 0.991l = −10→10
2643 measured reflections3 standard reflections every 120 min
2478 independent reflections intensity decay: 1%
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.054H-atom parameters constrained
wR(F2) = 0.156 w = 1/[σ2(Fo2) + (0.04P)2 + 2.02P]
where P = (Fo2 + 2Fc2)/3
S = 1.00(Δ/σ)max < 0.001
2478 reflectionsΔρmax = 0.23 e Å−3
184 parametersΔρmin = −0.27 e Å−3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.040 (3)
Crystal data top
C16H14O4V = 1365.3 (5) Å3
Mr = 270.27Z = 4
Monoclinic, P21/nMo Kα radiation
a = 8.8380 (18) ŵ = 0.10 mm−1
b = 18.204 (4) ÅT = 294 K
c = 8.9620 (18) Å0.30 × 0.20 × 0.10 mm
β = 108.75 (3)°
Data collection top
Enraf–Nonius CAD-4
diffractometer		1645 reflections with I > 2σ(I)
Absorption correction: ψ scan
(North et al., 1968)		Rint = 0.026
Tmin = 0.972, Tmax = 0.991θmax = 25.3°
2643 measured reflections3 standard reflections every 120 min
2478 independent reflections intensity decay: 1%
Refinement top
R[F2 > 2σ(F2)] = 0.054H-atom parameters constrained
wR(F2) = 0.156Δρmax = 0.23 e Å−3
S = 1.00Δρmin = −0.27 e Å−3
2478 reflectionsAbsolute structure: ?
184 parametersFlack parameter: ?
0 restraintsRogers parameter: ?
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
O10.0543 (3)0.18629 (18)0.4765 (3)0.0742 (8)
O20.0736 (3)0.22040 (12)0.7226 (3)0.0486 (6)
O30.2528 (3)0.08431 (13)0.7691 (2)0.0468 (6)
O40.1896 (4)−0.03274 (15)0.7923 (3)0.0762 (9)
C10.2647 (5)0.2666 (2)0.6182 (5)0.0750 (13)
H1A0.28740.27190.52090.113*
H1B0.35390.24370.69520.113*
H1C0.24630.31420.65530.113*
C20.1200 (5)0.2203 (2)0.5920 (5)0.0544 (9)
C3−0.0585 (4)0.17726 (18)0.7219 (4)0.0438 (8)
C4−0.2080 (4)0.1915 (2)0.6172 (4)0.0576 (10)
H4A−0.22170.22690.53920.069*
C5−0.3376 (4)0.1522 (2)0.6297 (5)0.0649 (11)
H5A−0.43910.16130.55960.078*
C6−0.3171 (5)0.1001 (2)0.7448 (5)0.0656 (11)
H6A−0.40470.07380.75200.079*
C7−0.1664 (4)0.0864 (2)0.8507 (4)0.0522 (9)
H7A−0.15410.05110.92870.063*
C8−0.0327 (4)0.12500 (18)0.8416 (4)0.0406 (8)
C90.1255 (4)0.11569 (17)0.9635 (4)0.0395 (7)
C100.1422 (4)0.12691 (18)1.1210 (4)0.0466 (8)
H10A0.05250.13711.15020.056*
C110.2908 (4)0.1231 (2)1.2353 (4)0.0546 (9)
H11A0.30030.13211.34010.065*
C120.4247 (4)0.1062 (2)1.1957 (4)0.0547 (9)
H12A0.52420.10391.27320.066*
C130.4108 (4)0.09252 (19)1.0405 (4)0.0512 (9)
H13A0.50050.08061.01260.061*
C140.2620 (4)0.09669 (17)0.9267 (4)0.0418 (8)
C150.2136 (4)0.0154 (2)0.7134 (4)0.0475 (8)
C160.2087 (5)0.0091 (2)0.5468 (4)0.0636 (11)
H16A0.1746−0.03950.50880.095*
H16B0.31340.01800.54000.095*
H16C0.13510.04450.48390.095*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0705 (19)0.099 (2)0.0555 (17)−0.0022 (17)0.0229 (14)−0.0038 (16)
O20.0470 (13)0.0506 (14)0.0484 (13)−0.0043 (11)0.0156 (11)0.0034 (11)
O30.0520 (14)0.0505 (14)0.0426 (13)0.0022 (11)0.0217 (11)−0.0004 (11)
O40.117 (3)0.0578 (17)0.0618 (17)−0.0175 (17)0.0403 (17)−0.0039 (14)
C10.069 (3)0.081 (3)0.083 (3)−0.009 (2)0.034 (2)0.013 (2)
C20.056 (2)0.056 (2)0.050 (2)0.0067 (18)0.0175 (18)0.0116 (18)
C30.0397 (18)0.0448 (19)0.0473 (19)0.0003 (15)0.0147 (15)−0.0042 (15)
C40.054 (2)0.063 (2)0.051 (2)0.0104 (19)0.0100 (18)−0.0078 (18)
C50.040 (2)0.085 (3)0.064 (3)0.009 (2)0.0099 (18)−0.016 (2)
C60.047 (2)0.085 (3)0.071 (3)−0.012 (2)0.026 (2)−0.025 (2)
C70.048 (2)0.060 (2)0.054 (2)−0.0084 (17)0.0233 (17)−0.0084 (17)
C80.0348 (17)0.0478 (19)0.0421 (18)0.0007 (14)0.0163 (14)−0.0056 (15)
C90.0432 (18)0.0389 (18)0.0394 (17)−0.0009 (14)0.0172 (14)0.0023 (14)
C100.0465 (19)0.053 (2)0.0437 (19)0.0001 (16)0.0189 (16)−0.0018 (15)
C110.064 (2)0.060 (2)0.0405 (19)0.0014 (19)0.0183 (18)−0.0020 (17)
C120.046 (2)0.063 (2)0.050 (2)0.0075 (17)0.0078 (17)0.0027 (17)
C130.0414 (19)0.059 (2)0.055 (2)0.0038 (16)0.0175 (16)0.0047 (17)
C140.0463 (19)0.0433 (18)0.0383 (17)0.0032 (15)0.0168 (15)0.0020 (14)
C150.0423 (19)0.054 (2)0.048 (2)0.0024 (16)0.0171 (16)−0.0055 (17)
C160.072 (3)0.077 (3)0.047 (2)0.010 (2)0.0257 (19)−0.0065 (19)
Geometric parameters (Å, °) top
O1—C21.185 (4)C7—C81.400 (4)
O2—C21.359 (4)C7—H7A0.9300
O2—C31.406 (4)C8—C91.482 (4)
O3—C151.353 (4)C9—C101.386 (4)
O3—C141.406 (4)C9—C141.393 (4)
O4—C151.187 (4)C10—C111.383 (5)
C1—C21.487 (5)C10—H10A0.9300
C1—H1A0.9600C11—C121.376 (5)
C1—H1B0.9600C11—H11A0.9300
C1—H1C0.9600C12—C131.379 (5)
C3—C41.377 (5)C12—H12A0.9300
C3—C81.396 (4)C13—C141.384 (5)
C4—C51.385 (6)C13—H13A0.9300
C4—H4A0.9300C15—C161.484 (5)
C5—C61.370 (6)C16—H16A0.9600
C5—H5A0.9300C16—H16B0.9600
C6—C71.387 (5)C16—H16C0.9600
C6—H6A0.9300
C2—O2—C3118.4 (3)C7—C8—C9120.9 (3)
C15—O3—C14116.4 (3)C10—C9—C14117.4 (3)
C2—C1—H1A109.5C10—C9—C8120.0 (3)
C2—C1—H1B109.5C14—C9—C8122.5 (3)
H1A—C1—H1B109.5C11—C10—C9120.8 (3)
C2—C1—H1C109.5C11—C10—H10A119.6
H1A—C1—H1C109.5C9—C10—H10A119.6
H1B—C1—H1C109.5C12—C11—C10120.7 (3)
O1—C2—O2123.7 (4)C12—C11—H11A119.7
O1—C2—C1126.1 (4)C10—C11—H11A119.7
O2—C2—C1110.2 (3)C11—C12—C13119.7 (3)
C4—C3—C8122.4 (3)C11—C12—H12A120.1
C4—C3—O2120.8 (3)C13—C12—H12A120.1
C8—C3—O2116.6 (3)C12—C13—C14119.3 (3)
C3—C4—C5119.0 (4)C12—C13—H13A120.4
C3—C4—H4A120.5C14—C13—H13A120.4
C5—C4—H4A120.5C13—C14—C9122.0 (3)
C6—C5—C4120.4 (4)C13—C14—O3117.8 (3)
C6—C5—H5A119.8C9—C14—O3120.2 (3)
C4—C5—H5A119.8O4—C15—O3122.6 (3)
C5—C6—C7120.3 (4)O4—C15—C16126.0 (4)
C5—C6—H6A119.8O3—C15—C16111.4 (3)
C7—C6—H6A119.8C15—C16—H16A109.5
C6—C7—C8120.8 (4)C15—C16—H16B109.5
C6—C7—H7A119.6H16A—C16—H16B109.5
C8—C7—H7A119.6C15—C16—H16C109.5
C3—C8—C7117.0 (3)H16A—C16—H16C109.5
C3—C8—C9121.8 (3)H16B—C16—H16C109.5
C3—O2—C2—O10.7 (5)C3—C8—C9—C14−60.2 (4)
C3—O2—C2—C1−177.8 (3)C7—C8—C9—C14126.0 (3)
C2—O2—C3—C4−63.2 (4)C14—C9—C10—C113.4 (5)
C2—O2—C3—C8122.9 (3)C8—C9—C10—C11−175.8 (3)
C8—C3—C4—C5−0.5 (5)C9—C10—C11—C12−1.8 (5)
O2—C3—C4—C5−174.1 (3)C10—C11—C12—C13−0.2 (6)
C3—C4—C5—C60.1 (6)C11—C12—C13—C140.5 (5)
C4—C5—C6—C70.4 (6)C12—C13—C14—C91.2 (5)
C5—C6—C7—C8−0.4 (6)C12—C13—C14—O3178.4 (3)
C4—C3—C8—C70.6 (5)C10—C9—C14—C13−3.1 (5)
O2—C3—C8—C7174.3 (3)C8—C9—C14—C13176.0 (3)
C4—C3—C8—C9−173.5 (3)C10—C9—C14—O3179.8 (3)
O2—C3—C8—C90.3 (4)C8—C9—C14—O3−1.1 (5)
C6—C7—C8—C3−0.1 (5)C15—O3—C14—C1396.1 (4)
C6—C7—C8—C9174.0 (3)C15—O3—C14—C9−86.7 (4)
C3—C8—C9—C10118.9 (3)C14—O3—C15—O4−0.8 (5)
C7—C8—C9—C10−54.9 (4)C14—O3—C15—C16−179.6 (3)
Acknowledgements top

The authors thank the Center of Testing and Analysis, Nanjing University, for support.

references
References top

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19.

Enraf–Nonius (1989). CAD-4 Software. Enraf–Nonius, Delft. The Netherlands.

Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany.

North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351–359.

Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.