Acta Cryst. (2010). E66, o448 [ doi:10.1107/S1600536810002370 ]
In the molecular structure of the title compound, C20H15NO2, the isoindolin-1-one unit is planar, the maximum atomic deviation being 0.048 (2) Å. The two biphenyl rings are twisted with respect to the isoindolin-1-one plane, making dihedral angles of 33.21 (9) and 33.34 (9)°. The two benzene rings of the biphenyl substituent are oriented at a dihedral angle of 35.43 (11)° to each other. An intramolecular O-H
O interaction occurs and intermolecular C-HO hydrogen bonding is present in the crystal structure.
A 10 mL flask was charged with Pd(OAc)2 (6.7 mg, 0.03 mmol), 1,1'-bis(diphenylphosphino)ferrocene (dppf) (16.6 mg, 0.03 mmol), and K2CO3 (83.0 mg, 0.6 mmol). The loaded flask was evacuated and backfilled with N2 (repeated for three times). To the degassed flask was added a solution of 4-(2'-bromobenzyl)-6-phenylbenz[1,4]oxazine-2,3-dione (122.4 mg, 0.3 mmol) in degassed DMA (3 mL). The resultant mixture was heated at 393 K for 2 h under a nitrogen atmosphere. After cooling to room temperature, the reaction was quenched by adding CH2Cl2 (20 mL), and the resultant mixture was washing with H2O (3 × 10 mL) to remove DMA. The organic layer was washed with brine, dried over anhydrous Na2SO4, filtrated, and concentrated under reduced pressure. The residue was purified by column chromatography over silica gel with elution by 20% EtOAc in petroleum ether (333–363 K) to give 2-(4'-hydroxybiphenyl-3'-yl)isoindolin- 1-one (70.0 mg, 78%), m.p. 453–454 K (CH2Cl2-hexane). Single crystals suitable for X-ray diffraction of the title compound were grown in the mixed solvent of CH2Cl2 and hexane.
H atoms were placed in calculated positions with C—H = 0.93–0.97 and O—H = 0.82 Å, and included in the refinement in riding model with Uiso(H) = 1.2Ueq(C) and 1.5Ueq(O). As no significant anomalous scattering effects were observed, Friedel pairs were merged.
Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO (Rigaku, 1998); data reduction: CrystalStructure (Rigaku/MSC, 2002); program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).
![[Figure 1]](./xu2719fig1thm.gif)
| Fig. 1. The molecular structure of (I). Displacement ellipsoids are drawn at 40% probability level and H atoms are shown as small circles of arbitary radii. |
| C20H15NO2 | Dx = 1.355 Mg m−3 |
| Mr = 301.33 | Cu Kα radiation, λ = 1.54184 Å |
| Tetragonal, P43212 | Cell parameters from 3246 reflections |
| Hall symbol: P 4nw 2abw | θ = 3.5–65.0° |
| a = 7.5123 (2) Å | µ = 0.70 mm−1 |
| c = 52.3543 (17) Å | T = 294 K |
| V = 2954.60 (15) Å3 | Prism, colorless |
| Z = 8 | 0.32 × 0.22 × 0.20 mm |
| F(000) = 1264 |
| Rigaku R-AXIS RAPID IP diffractometer | 1676 independent reflections |
| Radiation source: fine-focus sealed tube | 1556 reflections with I > 2σ(I) |
| graphite | Rint = 0.041 |
| Detector resolution: 10.0 pixels mm-1 | θmax = 67.1°, θmin = 3.4° |
| ω scans | h = −8→8 |
| Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | k = −8→8 |
| Tmin = 0.822, Tmax = 0.900 | l = −56→61 |
| 10482 measured reflections |
| 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)] = 0.031 | H-atom parameters constrained |
| wR(F2) = 0.077 | w = 1/[σ2(Fo2) + (0.0383P)2 + 0.7354P] where P = (Fo2 + 2Fc2)/3 |
| S = 1.08 | (Δ/σ)max = 0.001 |
| 1676 reflections | Δρmax = 0.16 e Å−3 |
| 210 parameters | Δρmin = −0.15 e Å−3 |
| 0 restraints | Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
| Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.00108 (16) |
| C20H15NO2 | Z = 8 |
| Mr = 301.33 | Cu Kα radiation |
| Tetragonal, P43212 | µ = 0.70 mm−1 |
| a = 7.5123 (2) Å | T = 294 K |
| c = 52.3543 (17) Å | 0.32 × 0.22 × 0.20 mm |
| V = 2954.60 (15) Å3 |
| Rigaku R-AXIS RAPID IP diffractometer | 1676 independent reflections |
| Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | 1556 reflections with I > 2σ(I) |
| Tmin = 0.822, Tmax = 0.900 | Rint = 0.041 |
| 10482 measured reflections | θmax = 67.1° |
| R[F2 > 2σ(F2)] = 0.031 | H-atom parameters constrained |
| wR(F2) = 0.077 | Δρmax = 0.16 e Å−3 |
| S = 1.08 | Δρmin = −0.15 e Å−3 |
| 1676 reflections | Absolute structure: ? |
| 210 parameters | Flack parameter: ? |
| 0 restraints | Rogers parameter: ? |
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 | 1.19213 (19) | 0.1923 (2) | 0.94864 (3) | 0.0332 (4) | |
| O2 | 1.2708 (2) | −0.0751 (2) | 0.92001 (2) | 0.0343 (4) | |
| H2 | 1.2642 | 0.0021 | 0.9310 | 0.052* | |
| N1 | 0.9322 (2) | 0.1133 (2) | 0.92751 (3) | 0.0227 (4) | |
| C1 | 0.6483 (3) | 0.0856 (3) | 0.83609 (4) | 0.0298 (5) | |
| H1 | 0.5924 | 0.0596 | 0.8515 | 0.036* | |
| C2 | 0.5463 (3) | 0.1296 (3) | 0.81496 (4) | 0.0349 (5) | |
| H2A | 0.4229 | 0.1325 | 0.8163 | 0.042* | |
| C3 | 0.6272 (3) | 0.1694 (3) | 0.79190 (4) | 0.0348 (5) | |
| H3 | 0.5589 | 0.2004 | 0.7778 | 0.042* | |
| C4 | 0.8105 (3) | 0.1625 (3) | 0.79011 (3) | 0.0326 (5) | |
| H4 | 0.8655 | 0.1875 | 0.7746 | 0.039* | |
| C5 | 0.9131 (3) | 0.1186 (3) | 0.81118 (3) | 0.0282 (5) | |
| H5 | 1.0364 | 0.1150 | 0.8097 | 0.034* | |
| C6 | 0.8337 (3) | 0.0797 (3) | 0.83461 (3) | 0.0239 (4) | |
| C7 | 0.9453 (3) | 0.0361 (3) | 0.85723 (3) | 0.0242 (4) | |
| C8 | 1.1044 (3) | −0.0590 (3) | 0.85490 (3) | 0.0282 (5) | |
| H8 | 1.1399 | −0.1008 | 0.8390 | 0.034* | |
| C9 | 1.2093 (3) | −0.0914 (3) | 0.87605 (4) | 0.0297 (5) | |
| H9 | 1.3153 | −0.1539 | 0.8741 | 0.036* | |
| C10 | 1.1605 (3) | −0.0328 (3) | 0.90024 (3) | 0.0266 (5) | |
| C11 | 0.9992 (3) | 0.0590 (3) | 0.90309 (3) | 0.0232 (4) | |
| C12 | 0.8957 (3) | 0.0937 (3) | 0.88161 (3) | 0.0231 (4) | |
| H12 | 0.7902 | 0.1572 | 0.8835 | 0.028* | |
| C13 | 1.0282 (3) | 0.1716 (3) | 0.94795 (3) | 0.0252 (4) | |
| C14 | 0.7394 (3) | 0.1129 (3) | 0.93267 (3) | 0.0232 (4) | |
| H14A | 0.6893 | −0.0053 | 0.9306 | 0.028* | |
| H14B | 0.6770 | 0.1950 | 0.9215 | 0.028* | |
| C15 | 0.7311 (3) | 0.1730 (3) | 0.96011 (3) | 0.0224 (4) | |
| C16 | 0.9020 (3) | 0.2040 (3) | 0.96878 (3) | 0.0236 (4) | |
| C17 | 0.9354 (3) | 0.2596 (3) | 0.99368 (3) | 0.0282 (5) | |
| H17 | 1.0510 | 0.2791 | 0.9994 | 0.034* | |
| C18 | 0.7913 (3) | 0.2848 (3) | 1.00959 (3) | 0.0295 (5) | |
| H18 | 0.8097 | 0.3196 | 1.0264 | 0.035* | |
| C19 | 0.6183 (3) | 0.2586 (3) | 1.00072 (4) | 0.0289 (5) | |
| H19 | 0.5228 | 0.2788 | 1.0116 | 0.035* | |
| C20 | 0.5861 (3) | 0.2026 (3) | 0.97573 (3) | 0.0272 (4) | |
| H20 | 0.4706 | 0.1857 | 0.9698 | 0.033* |
| U11 | U22 | U33 | U12 | U13 | U23 | |
| O1 | 0.0203 (8) | 0.0453 (10) | 0.0340 (7) | −0.0038 (7) | −0.0027 (6) | −0.0023 (7) |
| O2 | 0.0300 (8) | 0.0425 (10) | 0.0305 (7) | 0.0109 (7) | −0.0058 (6) | 0.0042 (6) |
| N1 | 0.0195 (8) | 0.0270 (9) | 0.0216 (7) | −0.0004 (7) | −0.0002 (6) | 0.0013 (6) |
| C1 | 0.0282 (11) | 0.0328 (12) | 0.0283 (9) | −0.0004 (9) | 0.0017 (8) | −0.0037 (9) |
| C2 | 0.0233 (11) | 0.0391 (13) | 0.0423 (11) | 0.0032 (9) | −0.0050 (9) | −0.0101 (10) |
| C3 | 0.0365 (13) | 0.0347 (13) | 0.0332 (10) | 0.0021 (10) | −0.0129 (9) | −0.0059 (9) |
| C4 | 0.0382 (13) | 0.0369 (13) | 0.0226 (9) | −0.0042 (10) | −0.0041 (9) | −0.0032 (9) |
| C5 | 0.0257 (11) | 0.0323 (12) | 0.0265 (9) | −0.0009 (9) | −0.0011 (8) | −0.0033 (8) |
| C6 | 0.0245 (10) | 0.0211 (10) | 0.0260 (9) | 0.0004 (8) | −0.0004 (8) | −0.0057 (8) |
| C7 | 0.0247 (11) | 0.0224 (10) | 0.0255 (9) | −0.0019 (8) | 0.0021 (8) | −0.0001 (8) |
| C8 | 0.0296 (11) | 0.0277 (11) | 0.0274 (9) | 0.0031 (10) | 0.0052 (8) | −0.0017 (8) |
| C9 | 0.0265 (12) | 0.0291 (11) | 0.0336 (9) | 0.0065 (9) | 0.0043 (9) | 0.0014 (9) |
| C10 | 0.0226 (11) | 0.0268 (11) | 0.0302 (9) | 0.0014 (8) | 0.0004 (8) | 0.0042 (8) |
| C11 | 0.0246 (10) | 0.0218 (10) | 0.0232 (9) | −0.0019 (8) | 0.0031 (7) | 0.0013 (8) |
| C12 | 0.0204 (10) | 0.0231 (10) | 0.0259 (9) | 0.0004 (8) | 0.0005 (7) | 0.0000 (8) |
| C13 | 0.0233 (11) | 0.0255 (11) | 0.0268 (9) | −0.0021 (8) | −0.0037 (8) | 0.0032 (8) |
| C14 | 0.0208 (10) | 0.0281 (10) | 0.0206 (8) | −0.0015 (8) | −0.0006 (7) | 0.0010 (7) |
| C15 | 0.0265 (11) | 0.0205 (10) | 0.0202 (8) | −0.0014 (8) | −0.0026 (7) | 0.0035 (7) |
| C16 | 0.0244 (10) | 0.0220 (10) | 0.0245 (8) | −0.0004 (8) | −0.0009 (8) | 0.0014 (8) |
| C17 | 0.0292 (11) | 0.0268 (11) | 0.0286 (9) | −0.0015 (9) | −0.0072 (8) | −0.0027 (8) |
| C18 | 0.0388 (12) | 0.0278 (11) | 0.0218 (8) | 0.0020 (9) | −0.0041 (8) | −0.0015 (8) |
| C19 | 0.0303 (11) | 0.0313 (12) | 0.0253 (8) | 0.0021 (9) | 0.0029 (8) | 0.0000 (9) |
| C20 | 0.0234 (11) | 0.0319 (12) | 0.0263 (8) | −0.0008 (9) | −0.0012 (8) | 0.0032 (8) |
| O1—C13 | 1.242 (3) | C8—H8 | 0.9300 |
| O2—C10 | 1.363 (2) | C9—C10 | 1.390 (3) |
| O2—H2 | 0.8200 | C9—H9 | 0.9300 |
| N1—C13 | 1.363 (2) | C10—C11 | 1.402 (3) |
| N1—C11 | 1.433 (2) | C11—C12 | 1.393 (3) |
| N1—C14 | 1.474 (3) | C12—H12 | 0.9300 |
| C1—C2 | 1.386 (3) | C13—C16 | 1.466 (3) |
| C1—C6 | 1.396 (3) | C14—C15 | 1.507 (2) |
| C1—H1 | 0.9300 | C14—H14A | 0.9700 |
| C2—C3 | 1.384 (3) | C14—H14B | 0.9700 |
| C2—H2A | 0.9300 | C15—C20 | 1.380 (3) |
| C3—C4 | 1.381 (3) | C15—C16 | 1.382 (3) |
| C3—H3 | 0.9300 | C16—C17 | 1.392 (3) |
| C4—C5 | 1.386 (3) | C17—C18 | 1.379 (3) |
| C4—H4 | 0.9300 | C17—H17 | 0.9300 |
| C5—C6 | 1.395 (3) | C18—C19 | 1.394 (3) |
| C5—H5 | 0.9300 | C18—H18 | 0.9300 |
| C6—C7 | 1.487 (3) | C19—C20 | 1.396 (3) |
| C7—C8 | 1.398 (3) | C19—H19 | 0.9300 |
| C7—C12 | 1.398 (3) | C20—H20 | 0.9300 |
| C8—C9 | 1.381 (3) | ||
| C10—O2—H2 | 109.5 | C12—C11—C10 | 119.27 (17) |
| C13—N1—C11 | 127.30 (17) | C12—C11—N1 | 118.10 (17) |
| C13—N1—C14 | 112.13 (15) | C10—C11—N1 | 122.59 (16) |
| C11—N1—C14 | 120.56 (15) | C11—C12—C7 | 122.03 (18) |
| C2—C1—C6 | 121.00 (19) | C11—C12—H12 | 119.0 |
| C2—C1—H1 | 119.5 | C7—C12—H12 | 119.0 |
| C6—C1—H1 | 119.5 | O1—C13—N1 | 126.02 (18) |
| C3—C2—C1 | 120.3 (2) | O1—C13—C16 | 126.79 (18) |
| C3—C2—H2A | 119.8 | N1—C13—C16 | 107.19 (17) |
| C1—C2—H2A | 119.8 | N1—C14—C15 | 102.41 (15) |
| C4—C3—C2 | 119.3 (2) | N1—C14—H14A | 111.3 |
| C4—C3—H3 | 120.4 | C15—C14—H14A | 111.3 |
| C2—C3—H3 | 120.4 | N1—C14—H14B | 111.3 |
| C3—C4—C5 | 120.6 (2) | C15—C14—H14B | 111.3 |
| C3—C4—H4 | 119.7 | H14A—C14—H14B | 109.2 |
| C5—C4—H4 | 119.7 | C20—C15—C16 | 120.77 (16) |
| C4—C5—C6 | 120.8 (2) | C20—C15—C14 | 130.21 (18) |
| C4—C5—H5 | 119.6 | C16—C15—C14 | 108.99 (16) |
| C6—C5—H5 | 119.6 | C15—C16—C17 | 121.75 (18) |
| C5—C6—C1 | 117.99 (18) | C15—C16—C13 | 109.17 (15) |
| C5—C6—C7 | 120.34 (18) | C17—C16—C13 | 129.07 (19) |
| C1—C6—C7 | 121.66 (18) | C18—C17—C16 | 117.72 (19) |
| C8—C7—C12 | 117.76 (17) | C18—C17—H17 | 121.1 |
| C8—C7—C6 | 121.68 (16) | C16—C17—H17 | 121.1 |
| C12—C7—C6 | 120.54 (18) | C17—C18—C19 | 120.76 (17) |
| C9—C8—C7 | 120.55 (17) | C17—C18—H18 | 119.6 |
| C9—C8—H8 | 119.7 | C19—C18—H18 | 119.6 |
| C7—C8—H8 | 119.7 | C18—C19—C20 | 121.11 (19) |
| C8—C9—C10 | 121.62 (19) | C18—C19—H19 | 119.4 |
| C8—C9—H9 | 119.2 | C20—C19—H19 | 119.4 |
| C10—C9—H9 | 119.2 | C15—C20—C19 | 117.84 (19) |
| O2—C10—C9 | 117.24 (18) | C15—C20—H20 | 121.1 |
| O2—C10—C11 | 123.97 (17) | C19—C20—H20 | 121.1 |
| C9—C10—C11 | 118.74 (18) |
| D—H···A | D—H | H···A | D···A | D—H···A |
| O2—H2···O1 | 0.82 | 1.79 | 2.575 (2) | 162 |
| C20—H20···O1i | 0.93 | 2.37 | 3.283 (3) | 168 |
| Symmetry codes: (i) x−1, y, z. |
| D—H···A | D—H | H···A | D···A | D—H···A |
| O2—H2···O1 | 0.82 | 1.79 | 2.575 (2) | 162 |
| C20—H20···O1i | 0.93 | 2.37 | 3.283 (3) | 168 |
| Symmetry codes: (i) x−1, y, z. |
This work was supported by a research grant from the Natural Science Foundation of China (grant No. 20672092). Professor Wei-Min Dai is thanked for his valuable suggestions. Mr Ji-Yong Liu of the X-ray crystallography facility of Zhejiang University is acknowledged for his assistance with the crystal structural analysis.
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The title compound is a derivative of isoindolin-1-ones, which has been reported to deliver various biological activities such as neuritogenic activity (Nozawa et al., 1997); anxiolytic activity (Atack et al., 2006), survival motor neuron (SMN)-reporter upregulation activity (Lunn et al., 2004). In our laboratory the crystals of title compound was obtained unexpectedly when 4-(2'-bromobenzyl)-6-phenylbenz[1,4]oxazine-2,3-dione was subjected to the palladium-catalyzed intramolecular direct arylation (Wu et al., 2007). It seems that the substrate underwent an intramolecular decarbonylative coupling under the palladium-catalyzed conditions (Baudoin, 2007). The structure of the title compound has been characterized by spectroscopic methods with further confirmation by X-ray analysis. We report here its crystal strutture.
In the molecular structure of the title compound, there are one biphenyl moiety and one isoindolin-1-one linked through C11—N1 single bond (Fig. 1). The isoindolin-1-one moiety has a coplanar structure, the maximum atomic deviation being 0.048 (2) Å. Two phenyl rings are twisted with respect to the isoindolin-1-one plane with dihedral angles of 33.21 (9) and 33.34 (9)°, respectively. The two phenyl rings are oriented at 35.43 (11)°. The O—H···O and C—H···O hydrogen bonding is present in the crystal structure (Table 1).