organic compounds
2-Hydroxy-2-methyl-1-phenylindolin-3-one
aFaculty of Chemistry and Chemical Technology, University of Ljubljana, SI-1000 Ljubljana, Slovenia, and bDepartment of Chemistry, Faculty of Technology, Tomas Bata University in Zlin, Zlin 76272, Czech Republic
*Correspondence e-mail: andrej.pevec@fkkt.uni-lj.si
In the title compound, C15H13NO2, the indole and benzene rings make a dihedral angle of 60.61 (4)°. In the crystal, dimeric pairs (twofold symmetry) are formed via O—H⋯O hydrogen bonds.
Related literature
For naturally occurring 2-hydroxyindol-3-ones, see: Bhakuni et al. (1991). For intermediates of the 2-hydroxyindol-3-one in the total syntheses of some natural products including (+)-isatisine A, (±)-mersicarpine, hinckdentine A, mitomycin and others, see: Karadeolian & Kerr (2010); Magolan et al. (2008); Higuchi et al. (2009); Colandrea et al. (2003); Kawasaki et al. (2004). For recent syntheses of 2-hydroxyindol-3-ones, see: Coldham et al. (2010); Higuchi et al. (2010); Cariou et al. (2007); Hewitt & Shao (2006); Altinis Kiraz et al. (2004). For the synthesis of the title compound, see: Kafka et al. (2001).
Experimental
Crystal data
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Refinement
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Data collection: COLLECT (Hooft, 1998); cell DENZO and SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO and SCALEPACK; program(s) used to solve structure: SIR92 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009) and DIAMOND (Brandenburg, 1999); software used to prepare material for publication: WinGX (Farrugia, 1999).
Supporting information
https://doi.org/10.1107/S1600536811045302/tk5007sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536811045302/tk5007Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S1600536811045302/tk5007Isup3.cml
A mixture of 3-hydroxy-3-methyl-1-phenylquinoline-2,4(1H,3H)-dione (1.34 g, 5.0 mmol) in 1.3 M aqueous potassium hydroxide (30 ml) and benzene (120 ml) was vigorously stirred in the presence of air at room temperature for 30 min. Layers were separated, and the aqueous phase was extracted with benzene (5 x 20 ml). The combined organic layer was dried over K2CO3. The solvent was evaporated to dryness and the residue was crystallized from a mixture of benzene and cyclohexane to give crystals of the title compound (0.62 g, 2.6 mmol, 52%).
All H atoms were positioned geometrically and refined using a riding model, with C—H bond lengths constrained to 0.93 (aromatic-C—H) or 0.96 Å (methyl-C—H), and O—H = 0.82 Å, and with Uiso(H) values of 1.2Ueq(C) [for aromatic-H] or 1.5Ueq(C) [for OH and methyl-H].
The title compound, (I) (Fig. 1), was prepared as a part of a project focusing on molecular rearrangements of 3-hydroxyquinoline-2,4(1H,3H)-diones by the action of aqueous potassium hydroxide on 3-hydroxy-3-methyl-1-phenylquinoline-2,4(1H,3H)-dione in the presence of air (Kafka et al., 2001). Compounds containing the 2-hydroxyindol-3-one
are important intermediates in the total syntheses of some natural products including (+)-isatisine A, (±)-mersicarpine, hinckdentine A, mitomycin and others (Karadeolian & Kerr, 2010; Magolan et al., 2008; Higuchi et al., 2009; Colandrea et al., 2003; Kawasaki et al., 2004). New synthetic approaches towards 2-hydroxyindol-3-ones have been reported recently (Coldham et al., 2010; Higuchi et al., 2010; Cariou et al., 2007; Hewitt & Shao, 2006; Altinis Kiraz et al., 2004). A related 2-hydroxyindol-3-one compound, alkaloid melochicorine, was found in the plant Melochicoria corchorifolia (Bhakuni et al., 1991)In the
of (I) two molecules are connected by two intermolecular O—H···O hydrogen bonds (Fig. 2 & Table 1). The indole and benzene units make a dihedral angle of 60.61 (4)°. The aromatic rings have normal hydrophobic contacts with each other without any stacking interactions.For naturally occurring 2-hydroxyindol-3-ones, see: Bhakuni et al. (1991). For intermediates of the 2-hydroxyindol-3-one
in the total syntheses of some natural products including (+)-isatisine A, (±)-mersicarpine, hinckdentine A, mitomycin and others, see: Karadeolian & Kerr (2010); Magolan et al. (2008); Higuchi et al. (2009); Colandrea et al. (2003); Kawasaki et al. (2004). For recent syntheses of 2-hydroxyindol-3-ones, see: Coldham et al. (2010); Higuchi et al. (2010); Cariou et al. (2007); Hewitt & Shao (2006); Altinis Kiraz et al. (2004). For the synthesis of the title compound, see: Kafka et al. (2001).Data collection: COLLECT (Hooft, 1998); cell
DENZO and SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO and SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SIR92 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009) and DIAMOND (Brandenburg, 1999); software used to prepare material for publication: WinGX (Farrugia, 1999).C15H13NO2 | Dx = 1.317 Mg m−3 |
Mr = 239.26 | Melting point = 397–399 K |
Orthorhombic, Pbcn | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2n 2ab | Cell parameters from 3116 reflections |
a = 17.0146 (4) Å | θ = 1.0–27.5° |
b = 9.2193 (2) Å | µ = 0.09 mm−1 |
c = 15.3843 (4) Å | T = 295 K |
V = 2413.22 (10) Å3 | Prism, green |
Z = 8 | 0.55 × 0.40 × 0.30 mm |
F(000) = 1008 |
Nonius KappaCCD area-detector diffractometer | 2745 independent reflections |
Radiation source: fine-focus sealed tube | 1890 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.022 |
φ and ω scans | θmax = 27.5°, θmin = 3.5° |
Absorption correction: multi-scan (SCALEPACK; Otwinowski & Minor, 1997) | h = −22→21 |
Tmin = 0.953, Tmax = 0.974 | k = −11→11 |
5144 measured reflections | l = −19→19 |
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) = 0.116 | H-atom parameters constrained |
S = 1.04 | w = 1/[σ2(Fo2) + (0.0545P)2 + 0.3729P] where P = (Fo2 + 2Fc2)/3 |
2745 reflections | (Δ/σ)max = 0.0001 |
165 parameters | Δρmax = 0.15 e Å−3 |
0 restraints | Δρmin = −0.16 e Å−3 |
C15H13NO2 | V = 2413.22 (10) Å3 |
Mr = 239.26 | Z = 8 |
Orthorhombic, Pbcn | Mo Kα radiation |
a = 17.0146 (4) Å | µ = 0.09 mm−1 |
b = 9.2193 (2) Å | T = 295 K |
c = 15.3843 (4) Å | 0.55 × 0.40 × 0.30 mm |
Nonius KappaCCD area-detector diffractometer | 2745 independent reflections |
Absorption correction: multi-scan (SCALEPACK; Otwinowski & Minor, 1997) | 1890 reflections with I > 2σ(I) |
Tmin = 0.953, Tmax = 0.974 | Rint = 0.022 |
5144 measured reflections |
R[F2 > 2σ(F2)] = 0.043 | 0 restraints |
wR(F2) = 0.116 | H-atom parameters constrained |
S = 1.04 | Δρmax = 0.15 e Å−3 |
2745 reflections | Δρmin = −0.16 e Å−3 |
165 parameters |
Experimental. 210 frames in 4 sets of φ scans + ω scans. Rotation/frame = 2 °. Crystal-detector distance = 31 mm. Measuring time = 20 s/°. |
Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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 | 0.58436 (6) | 0.68168 (12) | 0.29672 (6) | 0.0524 (3) | |
O2 | 0.54290 (7) | 0.87398 (11) | 0.15350 (7) | 0.0562 (3) | |
H2 | 0.5002 | 0.8334 | 0.1584 | 0.084* | |
N1 | 0.59892 (7) | 0.68372 (12) | 0.06732 (7) | 0.0406 (3) | |
C1 | 0.59694 (8) | 0.51234 (15) | 0.17738 (9) | 0.0416 (3) | |
C2 | 0.60064 (8) | 0.53713 (15) | 0.08779 (9) | 0.0404 (3) | |
C3 | 0.60139 (9) | 0.42005 (16) | 0.03007 (11) | 0.0524 (4) | |
H3 | 0.6043 | 0.4339 | −0.0297 | 0.063* | |
C4 | 0.59754 (10) | 0.28280 (17) | 0.06584 (12) | 0.0614 (5) | |
H4 | 0.5981 | 0.2033 | 0.0286 | 0.074* | |
C5 | 0.59282 (10) | 0.25788 (18) | 0.15492 (13) | 0.0620 (5) | |
H5 | 0.5900 | 0.1635 | 0.1760 | 0.074* | |
C6 | 0.59237 (9) | 0.37246 (16) | 0.21147 (11) | 0.0526 (4) | |
H6 | 0.5891 | 0.3574 | 0.2711 | 0.063* | |
C7 | 0.59389 (8) | 0.65226 (15) | 0.22002 (9) | 0.0405 (3) | |
C8 | 0.60272 (8) | 0.76939 (15) | 0.14873 (9) | 0.0407 (3) | |
C9 | 0.68031 (10) | 0.84809 (18) | 0.15897 (11) | 0.0580 (4) | |
H9A | 0.6833 | 0.8899 | 0.2160 | 0.087* | |
H9B | 0.6840 | 0.9235 | 0.1161 | 0.087* | |
H9C | 0.7228 | 0.7808 | 0.1512 | 0.087* | |
C10 | 0.63405 (8) | 0.74129 (14) | −0.00952 (8) | 0.0392 (3) | |
C11 | 0.59874 (9) | 0.85663 (15) | −0.05174 (10) | 0.0472 (4) | |
H11 | 0.5505 | 0.8915 | −0.0326 | 0.057* | |
C12 | 0.63529 (10) | 0.92009 (17) | −0.12243 (11) | 0.0561 (4) | |
H12 | 0.6115 | 0.9979 | −0.1505 | 0.067* | |
C13 | 0.70639 (10) | 0.86900 (16) | −0.15140 (10) | 0.0534 (4) | |
H13 | 0.7310 | 0.9128 | −0.1986 | 0.064* | |
C14 | 0.74101 (9) | 0.75336 (16) | −0.11069 (10) | 0.0519 (4) | |
H14 | 0.7889 | 0.7181 | −0.1307 | 0.062* | |
C15 | 0.70513 (9) | 0.68883 (16) | −0.03994 (9) | 0.0473 (4) | |
H15 | 0.7288 | 0.6100 | −0.0127 | 0.057* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0523 (6) | 0.0653 (7) | 0.0397 (6) | 0.0011 (5) | 0.0016 (4) | −0.0021 (5) |
O2 | 0.0597 (7) | 0.0457 (6) | 0.0633 (7) | 0.0129 (5) | 0.0195 (6) | 0.0033 (5) |
N1 | 0.0443 (6) | 0.0384 (6) | 0.0389 (6) | −0.0010 (5) | 0.0037 (5) | −0.0020 (5) |
C1 | 0.0358 (7) | 0.0431 (8) | 0.0459 (8) | 0.0021 (6) | 0.0026 (6) | 0.0025 (6) |
C2 | 0.0351 (7) | 0.0387 (7) | 0.0475 (8) | −0.0014 (6) | 0.0029 (6) | −0.0022 (6) |
C3 | 0.0548 (9) | 0.0483 (9) | 0.0542 (9) | −0.0052 (7) | 0.0057 (7) | −0.0088 (7) |
C4 | 0.0595 (10) | 0.0419 (9) | 0.0829 (13) | −0.0044 (7) | 0.0082 (9) | −0.0142 (8) |
C5 | 0.0594 (10) | 0.0403 (8) | 0.0862 (13) | 0.0010 (7) | 0.0092 (9) | 0.0071 (8) |
C6 | 0.0465 (8) | 0.0496 (9) | 0.0618 (9) | 0.0053 (7) | 0.0063 (7) | 0.0127 (8) |
C7 | 0.0314 (7) | 0.0499 (8) | 0.0401 (7) | 0.0013 (6) | 0.0018 (6) | −0.0006 (6) |
C8 | 0.0405 (7) | 0.0397 (7) | 0.0419 (7) | 0.0012 (6) | 0.0065 (6) | −0.0058 (6) |
C9 | 0.0580 (10) | 0.0628 (10) | 0.0532 (9) | −0.0181 (8) | 0.0073 (7) | −0.0130 (8) |
C10 | 0.0424 (7) | 0.0395 (7) | 0.0357 (7) | −0.0021 (6) | 0.0003 (6) | −0.0035 (6) |
C11 | 0.0444 (8) | 0.0436 (8) | 0.0536 (9) | 0.0038 (6) | 0.0024 (7) | 0.0017 (7) |
C12 | 0.0632 (10) | 0.0459 (9) | 0.0592 (10) | 0.0057 (8) | 0.0005 (8) | 0.0119 (7) |
C13 | 0.0637 (10) | 0.0485 (9) | 0.0479 (9) | −0.0026 (7) | 0.0105 (7) | 0.0064 (7) |
C14 | 0.0497 (9) | 0.0532 (9) | 0.0530 (9) | 0.0035 (7) | 0.0121 (7) | 0.0001 (7) |
C15 | 0.0485 (8) | 0.0476 (8) | 0.0457 (8) | 0.0077 (7) | 0.0031 (6) | 0.0058 (6) |
O1—C7 | 1.2216 (16) | C7—C8 | 1.5464 (19) |
O2—C8 | 1.4040 (16) | C8—C9 | 1.515 (2) |
O2—H2 | 0.8200 | C9—H9A | 0.9600 |
N1—C2 | 1.3880 (17) | C9—H9B | 0.9600 |
N1—C10 | 1.4271 (17) | C9—H9C | 0.9600 |
N1—C8 | 1.4821 (17) | C10—C11 | 1.3833 (19) |
C1—C6 | 1.3943 (19) | C10—C15 | 1.3840 (19) |
C1—C2 | 1.398 (2) | C11—C12 | 1.383 (2) |
C1—C7 | 1.4481 (19) | C11—H11 | 0.9300 |
C2—C3 | 1.398 (2) | C12—C13 | 1.373 (2) |
C3—C4 | 1.381 (2) | C12—H12 | 0.9300 |
C3—H3 | 0.9300 | C13—C14 | 1.370 (2) |
C4—C5 | 1.392 (3) | C13—H13 | 0.9300 |
C4—H4 | 0.9300 | C14—C15 | 1.383 (2) |
C5—C6 | 1.368 (2) | C14—H14 | 0.9300 |
C5—H5 | 0.9300 | C15—H15 | 0.9300 |
C6—H6 | 0.9300 | ||
C8—O2—H2 | 109.5 | O2—C8—C7 | 111.84 (11) |
C2—N1—C10 | 122.77 (11) | N1—C8—C7 | 102.88 (10) |
C2—N1—C8 | 109.04 (11) | C9—C8—C7 | 110.21 (12) |
C10—N1—C8 | 118.92 (10) | C8—C9—H9A | 109.5 |
C6—C1—C2 | 121.62 (13) | C8—C9—H9B | 109.5 |
C6—C1—C7 | 130.66 (14) | H9A—C9—H9B | 109.5 |
C2—C1—C7 | 107.61 (12) | C8—C9—H9C | 109.5 |
N1—C2—C3 | 127.44 (14) | H9A—C9—H9C | 109.5 |
N1—C2—C1 | 112.44 (12) | H9B—C9—H9C | 109.5 |
C3—C2—C1 | 120.02 (13) | C11—C10—C15 | 119.30 (13) |
C4—C3—C2 | 116.99 (15) | C11—C10—N1 | 119.54 (12) |
C4—C3—H3 | 121.5 | C15—C10—N1 | 121.07 (12) |
C2—C3—H3 | 121.5 | C12—C11—C10 | 119.95 (14) |
C3—C4—C5 | 123.10 (16) | C12—C11—H11 | 120.0 |
C3—C4—H4 | 118.4 | C10—C11—H11 | 120.0 |
C5—C4—H4 | 118.4 | C13—C12—C11 | 120.44 (14) |
C6—C5—C4 | 119.92 (15) | C13—C12—H12 | 119.8 |
C6—C5—H5 | 120.0 | C11—C12—H12 | 119.8 |
C4—C5—H5 | 120.0 | C14—C13—C12 | 119.84 (14) |
C5—C6—C1 | 118.33 (15) | C14—C13—H13 | 120.1 |
C5—C6—H6 | 120.8 | C12—C13—H13 | 120.1 |
C1—C6—H6 | 120.8 | C13—C14—C15 | 120.34 (14) |
O1—C7—C1 | 129.80 (13) | C13—C14—H14 | 119.8 |
O1—C7—C8 | 122.88 (13) | C15—C14—H14 | 119.8 |
C1—C7—C8 | 107.30 (11) | C14—C15—C10 | 120.11 (14) |
O2—C8—N1 | 112.24 (11) | C14—C15—H15 | 119.9 |
O2—C8—C9 | 107.31 (12) | C10—C15—H15 | 119.9 |
N1—C8—C9 | 112.40 (11) | ||
C10—N1—C2—C3 | −31.0 (2) | C10—N1—C8—C9 | −37.57 (17) |
C8—N1—C2—C3 | −177.20 (14) | C2—N1—C8—C7 | −8.44 (13) |
C10—N1—C2—C1 | 152.51 (12) | C10—N1—C8—C7 | −156.10 (11) |
C8—N1—C2—C1 | 6.35 (15) | O1—C7—C8—O2 | −50.00 (18) |
C6—C1—C2—N1 | 175.46 (12) | C1—C7—C8—O2 | 128.43 (12) |
C7—C1—C2—N1 | −1.03 (15) | O1—C7—C8—N1 | −170.66 (12) |
C6—C1—C2—C3 | −1.3 (2) | C1—C7—C8—N1 | 7.77 (13) |
C7—C1—C2—C3 | −177.77 (13) | O1—C7—C8—C9 | 69.29 (16) |
N1—C2—C3—C4 | −175.56 (13) | C1—C7—C8—C9 | −112.29 (12) |
C1—C2—C3—C4 | 0.6 (2) | C2—N1—C10—C11 | 144.73 (13) |
C2—C3—C4—C5 | 0.2 (2) | C8—N1—C10—C11 | −72.24 (17) |
C3—C4—C5—C6 | −0.4 (3) | C2—N1—C10—C15 | −38.80 (19) |
C4—C5—C6—C1 | −0.2 (2) | C8—N1—C10—C15 | 104.23 (15) |
C2—C1—C6—C5 | 1.0 (2) | C15—C10—C11—C12 | −1.3 (2) |
C7—C1—C6—C5 | 176.62 (14) | N1—C10—C11—C12 | 175.20 (13) |
C6—C1—C7—O1 | −2.2 (3) | C10—C11—C12—C13 | 0.3 (2) |
C2—C1—C7—O1 | 173.84 (14) | C11—C12—C13—C14 | 0.7 (3) |
C6—C1—C7—C8 | 179.50 (14) | C12—C13—C14—C15 | −0.7 (2) |
C2—C1—C7—C8 | −4.44 (14) | C13—C14—C15—C10 | −0.3 (2) |
C2—N1—C8—O2 | −128.83 (11) | C11—C10—C15—C14 | 1.3 (2) |
C10—N1—C8—O2 | 83.51 (14) | N1—C10—C15—C14 | −175.13 (13) |
C2—N1—C8—C9 | 110.09 (13) |
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H2···O1i | 0.82 | 2.12 | 2.9014 (15) | 159 |
Symmetry code: (i) −x+1, y, −z+1/2. |
Experimental details
Crystal data | |
Chemical formula | C15H13NO2 |
Mr | 239.26 |
Crystal system, space group | Orthorhombic, Pbcn |
Temperature (K) | 295 |
a, b, c (Å) | 17.0146 (4), 9.2193 (2), 15.3843 (4) |
V (Å3) | 2413.22 (10) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 0.09 |
Crystal size (mm) | 0.55 × 0.40 × 0.30 |
Data collection | |
Diffractometer | Nonius KappaCCD area-detector |
Absorption correction | Multi-scan (SCALEPACK; Otwinowski & Minor, 1997) |
Tmin, Tmax | 0.953, 0.974 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 5144, 2745, 1890 |
Rint | 0.022 |
(sin θ/λ)max (Å−1) | 0.649 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.043, 0.116, 1.04 |
No. of reflections | 2745 |
No. of parameters | 165 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.15, −0.16 |
Computer programs: COLLECT (Hooft, 1998), DENZO and SCALEPACK (Otwinowski & Minor, 1997), SIR92 (Altomare et al., 1999), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009) and DIAMOND (Brandenburg, 1999), WinGX (Farrugia, 1999).
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H2···O1i | 0.82 | 2.12 | 2.9014 (15) | 159 |
Symmetry code: (i) −x+1, y, −z+1/2. |
Acknowledgements
Financial support from the Ministry of Education, Youth and Sports of the Czech Republic (project MSM7088352101) and the Slovenian Research Agency (programme P1–0230–0103, programme–0175, joint project BI–CZ/07–08–018 and joint project Nr 9–06–3 of programme KONTAKT) is gratefully acknowledged. This work was also partly supported through the infrastructure of the EN–FIST Centre of Excellence, Ljubljana.
References
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The title compound, (I) (Fig. 1), was prepared as a part of a project focusing on molecular rearrangements of 3-hydroxyquinoline-2,4(1H,3H)-diones by the action of aqueous potassium hydroxide on 3-hydroxy-3-methyl-1-phenylquinoline-2,4(1H,3H)-dione in the presence of air (Kafka et al., 2001). Compounds containing the 2-hydroxyindol-3-one substructure are important intermediates in the total syntheses of some natural products including (+)-isatisine A, (±)-mersicarpine, hinckdentine A, mitomycin and others (Karadeolian & Kerr, 2010; Magolan et al., 2008; Higuchi et al., 2009; Colandrea et al., 2003; Kawasaki et al., 2004). New synthetic approaches towards 2-hydroxyindol-3-ones have been reported recently (Coldham et al., 2010; Higuchi et al., 2010; Cariou et al., 2007; Hewitt & Shao, 2006; Altinis Kiraz et al., 2004). A related 2-hydroxyindol-3-one compound, alkaloid melochicorine, was found in the plant Melochicoria corchorifolia (Bhakuni et al., 1991)
In the crystal structure of (I) two molecules are connected by two intermolecular O—H···O hydrogen bonds (Fig. 2 & Table 1). The indole and benzene units make a dihedral angle of 60.61 (4)°. The aromatic rings have normal hydrophobic contacts with each other without any stacking interactions.