Acta Cryst. (2007). E63, o3936 [ doi:10.1107/S1600536807042195 ]
In the title compound, C23H28O6, the mean planes of the two benzene rings make a dihedral angle of 81.1 (2)°. A twofold rotation axis passes through the central C atom. The molecules are connected into chains via intermolecular O-H
O hydrogen bonds.
To a solution of bisphenol A (0.01 mol) in acetonitrile (50 ml), anhydrous potassium carbonate (0.02 mol) and ethyl 4-bromobutanoate were added (0.01 mol). The solution was refluxed for 6 h and then filtered. The filtrate was evaporated under reduced pressure and the residue was dissolved in water/ethanol (1:2 v/v), then sodium hydroxide (0.02 mol) was added. The solution was refluxed for 24 h, then acidified with dilute HCl. The crude product that precipitated was filtered off and crystals of the title compound (m.p. 458 K) were obtained by recrystallization from a mixture of water and ethanol (1:1). Elemental analysis calculated: C 68.98, H 7.05%; found: C 68.96, H 7.09%.
H atoms were placed in idealized locations with C—H = 0.93—0.97 Å or O—H = 0.82 Å and refined as riding with Uiso(H) = 1.2Ueq(C) or 1.5Ueq(O).
Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT (Siemens, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL (Sheldrick, 1997b).
![[Figure 1]](./bi2236fig1thm.gif)
| Fig. 1. The molecular structure of the title compound with displacement ellipsoids drawn at the 50% probability level for non-H atoms. |
![[Figure 2]](./bi2236fig2thm.gif)
| Fig. 2. Detail of (I) showing part of a hydrogen-bonded chain. H atoms have been omitted for clarity and the dashed lines represent the O—H···O hydrogen bonds. |
| C23H28O6 | F000 = 856 |
| Mr = 400.45 | Dx = 1.254 Mg m−3 Dm = 1.254 Mg m−3 Dm measured by not measured |
| Monoclinic, C2/c | Melting point: 458 K |
| Hall symbol: -C 2yc | Mo Kα radiation λ = 0.71073 Å |
| a = 17.7714 (6) Å | Cell parameters from 1720 reflections |
| b = 6.4837 (2) Å | θ = 2.4–20.6º |
| c = 18.9720 (7) Å | µ = 0.09 mm−1 |
| β = 103.997 (1)º | T = 295 (2) K |
| V = 2121.13 (12) Å3 | Block, colourless |
| Z = 4 | 0.32 × 0.28 × 0.22 mm |
| Bruker SMART CCD diffractometer | 1875 independent reflections |
| Radiation source: fine-focus sealed tube | 1270 reflections with I > 2σ(I) |
| Monochromator: graphite | Rint = 0.043 |
| T = 295(2) K | θmax = 25.0º |
| φ and ω scans | θmin = 2.2º |
| Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −20→20 |
| Tmin = 0.972, Tmax = 0.981 | k = −7→7 |
| 11585 measured reflections | l = −22→20 |
| Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
| Least-squares matrix: full | H-atom parameters constrained |
| R[F2 > 2σ(F2)] = 0.044 | w = 1/[σ2(Fo2) + (0.0503P)2 + 0.9594P] where P = (Fo2 + 2Fc2)/3 |
| wR(F2) = 0.122 | (Δ/σ)max = 0.002 |
| S = 1.04 | Δρmax = 0.16 e Å−3 |
| 1875 reflections | Δρmin = −0.14 e Å−3 |
| 135 parameters | Extinction correction: SHELXL97 (Sheldrick, 1997a), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
| Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0019 (5) |
| Secondary atom site location: difference Fourier map |
| C23H28O6 | V = 2121.13 (12) Å3 |
| Mr = 400.45 | Z = 4 |
| Monoclinic, C2/c | Mo Kα |
| a = 17.7714 (6) Å | µ = 0.09 mm−1 |
| b = 6.4837 (2) Å | T = 295 (2) K |
| c = 18.9720 (7) Å | 0.32 × 0.28 × 0.22 mm |
| β = 103.997 (1)º |
| Bruker SMART CCD diffractometer | 1875 independent reflections |
| Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 1270 reflections with I > 2σ(I) |
| Tmin = 0.972, Tmax = 0.981 | Rint = 0.043 |
| 11585 measured reflections |
| R[F2 > 2σ(F2)] = 0.044 | 135 parameters |
| wR(F2) = 0.122 | H-atom parameters constrained |
| S = 1.04 | Δρmax = 0.16 e Å−3 |
| 1875 reflections | Δρmin = −0.14 e Å−3 |
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 > 2sigma(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 | 0.03166 (9) | 0.2268 (3) | 0.03972 (9) | 0.0870 (6) | |
| O2 | 0.09455 (9) | −0.0031 (3) | −0.01063 (10) | 0.0840 (5) | |
| H2 | 0.0521 | −0.0601 | −0.0193 | 0.126* | |
| O3 | 0.23268 (7) | 0.7832 (2) | 0.13113 (8) | 0.0708 (5) | |
| C1 | 0.09057 (12) | 0.1693 (3) | 0.02182 (11) | 0.0620 (6) | |
| C2 | 0.16225 (12) | 0.2949 (3) | 0.03574 (12) | 0.0672 (6) | |
| H2A | 0.1723 | 0.3322 | −0.0106 | 0.081* | |
| H2B | 0.2051 | 0.2098 | 0.0613 | 0.081* | |
| C3 | 0.16129 (12) | 0.4892 (3) | 0.07901 (12) | 0.0689 (6) | |
| H3A | 0.1208 | 0.5803 | 0.0527 | 0.083* | |
| H3B | 0.1497 | 0.4552 | 0.1251 | 0.083* | |
| C4 | 0.23813 (12) | 0.5979 (3) | 0.09270 (12) | 0.0649 (6) | |
| H4A | 0.2786 | 0.5105 | 0.1211 | 0.078* | |
| H4B | 0.2509 | 0.6291 | 0.0470 | 0.078* | |
| C5 | 0.29946 (10) | 0.8949 (3) | 0.15747 (10) | 0.0527 (5) | |
| C6 | 0.29440 (12) | 1.0494 (3) | 0.20561 (12) | 0.0648 (6) | |
| H6 | 0.2477 | 1.0734 | 0.2181 | 0.078* | |
| C7 | 0.35832 (11) | 1.1692 (3) | 0.23550 (11) | 0.0601 (5) | |
| H7 | 0.3538 | 1.2729 | 0.2681 | 0.072* | |
| C8 | 0.42893 (10) | 1.1398 (3) | 0.21848 (10) | 0.0493 (5) | |
| C9 | 0.43194 (11) | 0.9847 (3) | 0.16914 (11) | 0.0606 (6) | |
| H9 | 0.4784 | 0.9611 | 0.1561 | 0.073* | |
| C10 | 0.36848 (11) | 0.8637 (3) | 0.13856 (11) | 0.0576 (5) | |
| H10 | 0.3725 | 0.7614 | 0.1053 | 0.069* | |
| C11 | 0.5000 | 1.2749 (4) | 0.2500 | 0.0572 (7) | |
| C12 | 0.51343 (13) | 1.4143 (3) | 0.18858 (14) | 0.0847 (8) | |
| H12A | 0.5272 | 1.3309 | 0.1518 | 0.127* | |
| H12B | 0.5547 | 1.5094 | 0.2078 | 0.127* | |
| H12C | 0.4668 | 1.4895 | 0.1678 | 0.127* |
| U11 | U22 | U33 | U12 | U13 | U23 | |
| O1 | 0.0724 (10) | 0.0757 (11) | 0.1180 (14) | −0.0211 (8) | 0.0329 (10) | −0.0354 (10) |
| O2 | 0.0712 (10) | 0.0739 (11) | 0.1062 (13) | −0.0166 (8) | 0.0202 (9) | −0.0331 (10) |
| O3 | 0.0567 (9) | 0.0637 (9) | 0.0892 (11) | −0.0136 (7) | 0.0123 (7) | −0.0165 (8) |
| C1 | 0.0641 (13) | 0.0555 (13) | 0.0629 (13) | −0.0108 (10) | 0.0081 (10) | −0.0081 (11) |
| C2 | 0.0635 (13) | 0.0633 (14) | 0.0718 (14) | −0.0130 (10) | 0.0103 (11) | −0.0059 (11) |
| C3 | 0.0648 (13) | 0.0631 (14) | 0.0747 (14) | −0.0158 (10) | 0.0090 (10) | −0.0088 (11) |
| C4 | 0.0659 (13) | 0.0552 (13) | 0.0690 (13) | −0.0126 (10) | 0.0076 (10) | −0.0063 (11) |
| C5 | 0.0496 (11) | 0.0476 (11) | 0.0558 (11) | −0.0034 (9) | 0.0029 (9) | 0.0008 (9) |
| C6 | 0.0544 (12) | 0.0660 (14) | 0.0764 (14) | −0.0056 (10) | 0.0202 (10) | −0.0119 (12) |
| C7 | 0.0605 (12) | 0.0524 (12) | 0.0663 (13) | −0.0005 (9) | 0.0133 (10) | −0.0108 (10) |
| C8 | 0.0471 (10) | 0.0388 (10) | 0.0558 (11) | 0.0038 (8) | 0.0004 (8) | 0.0040 (9) |
| C9 | 0.0474 (11) | 0.0545 (12) | 0.0778 (14) | 0.0019 (9) | 0.0112 (10) | −0.0102 (11) |
| C10 | 0.0554 (11) | 0.0502 (12) | 0.0633 (13) | 0.0009 (9) | 0.0067 (9) | −0.0110 (10) |
| C11 | 0.0531 (15) | 0.0379 (15) | 0.0730 (19) | 0.000 | 0.0003 (13) | 0.000 |
| C12 | 0.0674 (14) | 0.0584 (14) | 0.116 (2) | −0.0015 (11) | −0.0012 (13) | 0.0348 (14) |
| O1—C1 | 1.234 (2) | C6—C7 | 1.380 (3) |
| O2—C1 | 1.286 (2) | C6—H6 | 0.930 |
| O2—H2 | 0.820 | C7—C8 | 1.383 (3) |
| O3—C5 | 1.377 (2) | C7—H7 | 0.930 |
| O3—C4 | 1.421 (2) | C8—C9 | 1.384 (2) |
| C1—C2 | 1.481 (3) | C8—C11 | 1.534 (2) |
| C2—C3 | 1.506 (3) | C9—C10 | 1.381 (3) |
| C2—H2A | 0.970 | C9—H9 | 0.930 |
| C2—H2B | 0.970 | C10—H10 | 0.930 |
| C3—C4 | 1.502 (3) | C11—C8i | 1.534 (2) |
| C3—H3A | 0.970 | C11—C12i | 1.538 (3) |
| C3—H3B | 0.970 | C11—C12 | 1.538 (3) |
| C4—H4A | 0.970 | C12—H12A | 0.960 |
| C4—H4B | 0.970 | C12—H12B | 0.960 |
| C5—C6 | 1.373 (3) | C12—H12C | 0.960 |
| C5—C10 | 1.374 (3) | ||
| C1—O2—H2 | 109.5 | C5—C6—H6 | 119.9 |
| C5—O3—C4 | 118.11 (15) | C7—C6—H6 | 119.9 |
| O1—C1—O2 | 122.88 (19) | C6—C7—C8 | 122.01 (19) |
| O1—C1—C2 | 122.4 (2) | C6—C7—H7 | 119.0 |
| O2—C1—C2 | 114.8 (2) | C8—C7—H7 | 119.0 |
| C1—C2—C3 | 115.76 (19) | C7—C8—C9 | 116.36 (17) |
| C1—C2—H2A | 108.3 | C7—C8—C11 | 122.57 (16) |
| C3—C2—H2A | 108.3 | C9—C8—C11 | 121.04 (16) |
| C1—C2—H2B | 108.3 | C10—C9—C8 | 122.40 (18) |
| C3—C2—H2B | 108.3 | C10—C9—H9 | 118.8 |
| H2A—C2—H2B | 107.4 | C8—C9—H9 | 118.8 |
| C4—C3—C2 | 110.92 (18) | C5—C10—C9 | 119.77 (18) |
| C4—C3—H3A | 109.5 | C5—C10—H10 | 120.1 |
| C2—C3—H3A | 109.5 | C9—C10—H10 | 120.1 |
| C4—C3—H3B | 109.5 | C8—C11—C8i | 110.4 (2) |
| C2—C3—H3B | 109.5 | C8—C11—C12i | 111.51 (11) |
| H3A—C3—H3B | 108.0 | C8i—C11—C12i | 107.70 (11) |
| O3—C4—C3 | 108.26 (17) | C8—C11—C12 | 107.70 (11) |
| O3—C4—H4A | 110.0 | C8i—C11—C12 | 111.50 (11) |
| C3—C4—H4A | 110.0 | C12i—C11—C12 | 108.0 (3) |
| O3—C4—H4B | 110.0 | C11—C12—H12A | 109.5 |
| C3—C4—H4B | 110.0 | C11—C12—H12B | 109.5 |
| H4A—C4—H4B | 108.4 | H12A—C12—H12B | 109.5 |
| C6—C5—C10 | 119.17 (17) | C11—C12—H12C | 109.5 |
| C6—C5—O3 | 115.84 (17) | H12A—C12—H12C | 109.5 |
| C10—C5—O3 | 124.99 (18) | H12B—C12—H12C | 109.5 |
| C5—C6—C7 | 120.29 (18) | ||
| O1—C1—C2—C3 | 5.1 (3) | C7—C8—C9—C10 | −0.5 (3) |
| O2—C1—C2—C3 | −175.24 (19) | C11—C8—C9—C10 | −178.49 (18) |
| C1—C2—C3—C4 | 177.26 (18) | C6—C5—C10—C9 | 1.3 (3) |
| C5—O3—C4—C3 | 171.96 (17) | O3—C5—C10—C9 | −179.46 (18) |
| C2—C3—C4—O3 | 177.79 (17) | C8—C9—C10—C5 | −0.5 (3) |
| C4—O3—C5—C6 | −167.99 (18) | C7—C8—C11—C8i | 130.0 (2) |
| C4—O3—C5—C10 | 12.7 (3) | C9—C8—C11—C8i | −52.07 (14) |
| C10—C5—C6—C7 | −1.1 (3) | C7—C8—C11—C12i | 10.4 (3) |
| O3—C5—C6—C7 | 179.54 (18) | C9—C8—C11—C12i | −171.74 (18) |
| C5—C6—C7—C8 | 0.2 (3) | C7—C8—C11—C12 | −108.0 (2) |
| C6—C7—C8—C9 | 0.6 (3) | C9—C8—C11—C12 | 69.9 (2) |
| C6—C7—C8—C11 | 178.62 (18) |
| Symmetry codes: (i) −x+1, y, −z+1/2. |
| D—H···A | D—H | H···A | D···A | D—H···A |
| O2—H2···O1ii | 0.82 | 1.80 | 2.615 (2) | 170 |
| Symmetry codes: (ii) −x, −y, −z. |
| D—H···A | D—H | H···A | D···A | D—H···A |
| O2—H2···O1i | 0.82 | 1.80 | 2.615 (2) | 170 |
| Symmetry codes: (i) −x, −y, −z. |
This project was supported by the Postgraduate Foundation of Taishan University (No. Y05–2-02).
Ferguson, G., Glidewell, C., Gregson, R. M. & Lavender, E. S. (1999). Acta Cryst. B55, 573–590.
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (1997a). SHELXS97 and SHELXL97. University of Göttingen, Germany.
Sheldrick, G. M. (1997b). SHELXTL. Version 5.1. Bruker AXS Inc., Madison, Wisconsin, USA.
Siemens (1996). SMART and SAINT. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.
Staples, C. A., Dorn, P. B., Klecka, G. M., O'Block, S. T. & Harris, L. R. (1998). Chemosphere, 36, 2149–2173.
Bisphenol A is an intermediate in the production of polycarbonate and epoxy resins, flame retardants, and other specialty products. It is moderately soluble and appears to be released into the environment through its use (Staples et al., 1998). Crystal engineering using bisphenol A derivatives has received attention (Ferguson et al., 1999). In the course of our studies on bisphenol A derivatives, we have synthesized and determined the structure of the title compound (Fig. 1). In the crystal, the mean planes of the two benzene rings make a dihedral angle of 81.1 (2) °. Intermolecular O—H···O hydrogen bonds link the molecules into chains (Fig. 2).