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access1,4-Diphenylbutane-1,4-dione
aSchool of Chemical and Materials Engineering, Huangshi Institute of Technology, Huangshi 435003, People's Republic of China
*Correspondence e-mail: chwangzhigang@yahoo.com.cn
The of the title compound, C16H14O2, contains one half-molecule, located on a twofold rotation axis. In the molecule, the two benzene rings form a dihedral angle of 72.28 (2)°.
Related literature
For useful applications of 1,4-dicarbonyl compounds, see: Chiu & Sammes (1990![[Chiu, P.-K. & Sammes, M. P. (1990). Tetrahedron, 46, 3439-3456.]](../../../../../../logos/arrows/e_arr.gif "Chiu, P.-K. & Sammes, M. P. (1990). Tetrahedron, 46, 3439-3456.")
); Greatrex et al. (2003); Nagarajan & Shechter (1984). For details of the synthesis, see Nevar et al. (2000).
![[Scheme 1]](cv2479scheme1.gif)
Experimental
Crystal data
|
Data collection: SMART (Bruker, 1997); cell SAINT (Bruker, 1999); data reduction: SAINT; 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.
Supporting information
contains datablocks I, global. DOI: 10.1107/S1600536808038798/cv2479sup1.cif
Structure factors: contains datablock I. DOI: 10.1107/S1600536808038798/cv2479Isup2.hkl
The title compound was synthesized as previously described by Nevar et al. (2000). Colourless crystals suitable for X-ray data collection were obtained by slow evaporation of a 1:3 ratio EtOAc:cyclohexane solution at room temperture.
All H atoms were positioned geometrically (C—H = 0.93–0.97 Å) and refined as riding, allowing for of the methyl groups. The constraint Uiso(H) = 1.2 Ueq(C) or 1.5 Ueq(C) (methyl C) was applied. In the absence of anomalous scatterers, no attempt was made to establish the of the title compound, and 488 Friedel pairs were merged before the final refinement.
Data collection: SMART (Bruker, 1997); cell SMART (Bruker, 1997); data reduction: SAINT (Bruker, 1999); 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).
![[Figure 1]](./cv2479fig1thm.gif) | Fig. 1. View of the title molecule showing the atom-labelling scheme. The displacement ellipsoids are drawn at the 30% probability level [symmetry code: (a) -x, -y + 1, z]. |
| C16H14O2 | F(000) = 252 |
| Mr = 238.27 | Dx = 1.254 Mg m−3 |
| Orthorhombic, P21212 | Mo Kα radiation, λ = 0.71073 Å |
| Hall symbol: P 2 2ab | Cell parameters from 1423 reflections |
| a = 8.3781 (13) Å | θ = 2.8–22.3° |
| b = 14.161 (2) Å | µ = 0.08 mm−1 |
| c = 5.3186 (8) Å | T = 298 K |
| V = 631.00 (17) Å3 | Block, colourless |
| Z = 2 | 0.20 × 0.10 × 0.10 mm |
| Bruker SMART CCD area-detector diffractometer | 762 independent reflections |
| Radiation source: fine-focus sealed tube | 640 reflections with I > 2σ(I) |
| Graphite monochromator | Rint = 0.163 |
| ϕ and ω scans | θmax = 26.0°, θmin = 2.8° |
| Absorption correction: multi-scan (SADABS; Sheldrick, 1997) | h = −10→9 |
| Tmin = 0.984, Tmax = 0.992 | k = −16→17 |
| 4063 measured reflections | l = −6→6 |
| 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)] = 0.054 | Hydrogen site location: inferred from neighbouring sites |
| wR(F2) = 0.129 | H-atom parameters constrained |
| S = 1.05 | w = 1/[σ2(Fo2) + (0.0734P)2] where P = (Fo2 + 2Fc2)/3 |
| 762 reflections | (Δ/σ)max = 0.012 |
| 83 parameters | Δρmax = 0.20 e Å−3 |
| 0 restraints | Δρmin = −0.22 e Å−3 |
| C16H14O2 | V = 631.00 (17) Å3 |
| Mr = 238.27 | Z = 2 |
| Orthorhombic, P21212 | Mo Kα radiation |
| a = 8.3781 (13) Å | µ = 0.08 mm−1 |
| b = 14.161 (2) Å | T = 298 K |
| c = 5.3186 (8) Å | 0.20 × 0.10 × 0.10 mm |
| Bruker SMART CCD area-detector diffractometer | 762 independent reflections |
| Absorption correction: multi-scan (SADABS; Sheldrick, 1997) | 640 reflections with I > 2σ(I) |
| Tmin = 0.984, Tmax = 0.992 | Rint = 0.163 |
| 4063 measured reflections |
| R[F2 > 2σ(F2)] = 0.054 | 0 restraints |
| wR(F2) = 0.129 | H-atom parameters constrained |
| S = 1.05 | Δρmax = 0.20 e Å−3 |
| 762 reflections | Δρmin = −0.22 e Å−3 |
| 83 parameters |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
| x | y | z | Uiso*/Ueq | ||
| C1 | 0.1095 (3) | 0.30567 (15) | 0.2151 (4) | 0.0508 (6) | |
| C7 | 0.1070 (3) | 0.40988 (16) | 0.1653 (5) | 0.0574 (7) | |
| C4 | 0.1208 (3) | 0.11385 (19) | 0.3179 (6) | 0.0699 (7) | |
| H4 | 0.1241 | 0.0496 | 0.3532 | 0.084* | |
| C8 | 0.0072 (4) | 0.44647 (16) | −0.0468 (5) | 0.0670 (7) | |
| H8A | −0.0986 | 0.4191 | −0.0354 | 0.080* | |
| H8B | 0.0540 | 0.4263 | −0.2047 | 0.080* | |
| C3 | 0.2031 (3) | 0.17678 (17) | 0.4670 (5) | 0.0704 (8) | |
| H3 | 0.2625 | 0.1548 | 0.6026 | 0.085* | |
| C6 | 0.0283 (3) | 0.24197 (17) | 0.0654 (5) | 0.0608 (7) | |
| H6 | −0.0307 | 0.2634 | −0.0713 | 0.073* | |
| C2 | 0.1980 (3) | 0.27214 (16) | 0.4163 (5) | 0.0608 (7) | |
| H2 | 0.2541 | 0.3142 | 0.5176 | 0.073* | |
| O1 | 0.1843 (3) | 0.46221 (13) | 0.2966 (5) | 0.0984 (8) | |
| C5 | 0.0345 (3) | 0.14619 (18) | 0.1188 (6) | 0.0712 (8) | |
| H5 | −0.0206 | 0.1037 | 0.0177 | 0.085* |
| U11 | U22 | U33 | U12 | U13 | U23 | |
| C1 | 0.0464 (11) | 0.0571 (13) | 0.0490 (11) | 0.0054 (10) | 0.0025 (10) | −0.0053 (10) |
| C7 | 0.0558 (13) | 0.0561 (13) | 0.0603 (14) | 0.0011 (11) | −0.0034 (12) | −0.0105 (11) |
| C4 | 0.0636 (15) | 0.0595 (13) | 0.0867 (18) | 0.0061 (13) | 0.0053 (15) | 0.0043 (15) |
| C8 | 0.0839 (17) | 0.0614 (14) | 0.0555 (13) | 0.0048 (13) | −0.0040 (14) | −0.0074 (11) |
| C3 | 0.0658 (16) | 0.0769 (17) | 0.0686 (16) | 0.0155 (14) | −0.0023 (15) | 0.0091 (15) |
| C6 | 0.0613 (14) | 0.0604 (13) | 0.0607 (13) | −0.0011 (11) | −0.0092 (13) | −0.0065 (12) |
| C2 | 0.0560 (14) | 0.0676 (14) | 0.0589 (14) | 0.0046 (12) | −0.0060 (12) | −0.0094 (12) |
| O1 | 0.1149 (17) | 0.0632 (11) | 0.1172 (17) | −0.0067 (11) | −0.0544 (16) | −0.0120 (12) |
| C5 | 0.0696 (17) | 0.0597 (14) | 0.0843 (17) | −0.0059 (13) | −0.0060 (16) | −0.0117 (14) |
| C1—C6 | 1.382 (3) | C8—H8A | 0.9700 |
| C1—C2 | 1.386 (3) | C8—H8B | 0.9700 |
| C1—C7 | 1.499 (3) | C3—C2 | 1.378 (3) |
| C7—O1 | 1.207 (3) | C3—H3 | 0.9300 |
| C7—C8 | 1.496 (3) | C6—C5 | 1.387 (4) |
| C4—C5 | 1.361 (4) | C6—H6 | 0.9300 |
| C4—C3 | 1.378 (3) | C2—H2 | 0.9300 |
| C4—H4 | 0.9300 | C5—H5 | 0.9300 |
| C8—C8i | 1.521 (4) | ||
| C6—C1—C2 | 119.0 (2) | H8A—C8—H8B | 107.8 |
| C6—C1—C7 | 122.3 (2) | C4—C3—C2 | 120.4 (2) |
| C2—C1—C7 | 118.74 (19) | C4—C3—H3 | 119.8 |
| O1—C7—C8 | 121.5 (2) | C2—C3—H3 | 119.8 |
| O1—C7—C1 | 119.7 (2) | C1—C6—C5 | 120.1 (2) |
| C8—C7—C1 | 118.8 (2) | C1—C6—H6 | 119.9 |
| C5—C4—C3 | 119.7 (2) | C5—C6—H6 | 119.9 |
| C5—C4—H4 | 120.1 | C3—C2—C1 | 120.2 (2) |
| C3—C4—H4 | 120.1 | C3—C2—H2 | 119.9 |
| C7—C8—C8i | 112.9 (2) | C1—C2—H2 | 119.9 |
| C7—C8—H8A | 109.0 | C4—C5—C6 | 120.6 (2) |
| C8i—C8—H8A | 109.0 | C4—C5—H5 | 119.7 |
| C7—C8—H8B | 109.0 | C6—C5—H5 | 119.7 |
| C8i—C8—H8B | 109.0 | ||
| C6—C1—C7—O1 | −177.5 (3) | C2—C1—C6—C5 | 0.7 (3) |
| C2—C1—C7—O1 | 1.7 (4) | C7—C1—C6—C5 | 179.8 (3) |
| C6—C1—C7—C8 | 2.8 (3) | C4—C3—C2—C1 | 0.2 (4) |
| C2—C1—C7—C8 | −178.0 (2) | C6—C1—C2—C3 | −0.6 (4) |
| O1—C7—C8—C8i | −9.8 (4) | C7—C1—C2—C3 | −179.9 (2) |
| C1—C7—C8—C8i | 169.9 (3) | C3—C4—C5—C6 | −0.3 (4) |
| C5—C4—C3—C2 | 0.3 (4) | C1—C6—C5—C4 | −0.2 (4) |
| Symmetry code: (i) −x, −y+1, z. |
Experimental details
| Crystal data | |
| Chemical formula | C16H14O2 |
| Mr | 238.27 |
| Crystal system, space group | Orthorhombic, P21212 |
| Temperature (K) | 298 |
| a, b, c (Å) | 8.3781 (13), 14.161 (2), 5.3186 (8) |
| V (Å3) | 631.00 (17) |
| Z | 2 |
| Radiation type | Mo Kα |
| µ (mm−1) | 0.08 |
| Crystal size (mm) | 0.20 × 0.10 × 0.10 |
| Data collection | |
| Diffractometer | Bruker SMART CCD area-detector diffractometer |
| Absorption correction | Multi-scan (SADABS; Sheldrick, 1997) |
| Tmin, Tmax | 0.984, 0.992 |
| No. of measured, independent and observed [I > 2σ(I)] reflections | 4063, 762, 640 |
| Rint | 0.163 |
| (sin θ/λ)max (Å−1) | 0.617 |
| Refinement | |
| R[F2 > 2σ(F2)], wR(F2), S | 0.054, 0.129, 1.05 |
| No. of reflections | 762 |
| No. of parameters | 83 |
| H-atom treatment | H-atom parameters constrained |
| Δρmax, Δρmin (e Å−3) | 0.20, −0.22 |
Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1999), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).
Acknowledgements
The author is grateful to Ling Fan for a valuable discussion.
References
Bruker (1997). SMART. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (1999). SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Chiu, P.-K. & Sammes, M. P. (1990). Tetrahedron, 46, 3439–3456. CAS Google Scholar
Greatrex, B. W., Kimber, M. C., Taylor, D. K. & Tiekink, E. R. T. (2003). J. Org. Chem. 68, 4239–4246. Web of Science CSD CrossRef PubMed CAS Google Scholar
Nagarajan, G. & Shechter, H. (1984). J. Org. Chem. 49, 62–74. CrossRef CAS Web of Science Google Scholar
Nevar, N. M., Kel'in, A. V. & Kulinkovich, O. G. (2000). Synthesis, pp. 1259–1262. CrossRef Google Scholar
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Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
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| CRYSTALLOGRAPHIC COMMUNICATIONS |
1,4-Dicarbonyl compounds constitute key intermediates in various natural product syntheses, and they are important synthetic precursors of cyclopentenones, cyclopenta-1,3-diones, butenolides, and derivatives of furan and pyrrole (Chiu & Sammes, 1990; Greatrex et al., 2003; Nagarajan & Shechter, 1984). Herewith we present the title compound (I) (Fig. 1). The asymmetric unit of (I) contains a half of the molecule located on a twofold rotational axis. Two benzene rings form a dihedral angle of 72.28 (2)°.