2-Hy­droxy-2-methyl-1-phenyl­indolin-3-one

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.

Key indicators

• Single-crystal X-ray study
• T = 295 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.043
• wR factor = 0.116
• Data-to-parameter ratio = 16.6

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT910_ALERT_3_C Missing # of FCF Reflections Below Th(Min) .....          5
PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L=  0.600          8
PLAT913_ALERT_3_C Missing # of Very Strong Reflections in FCF ....          4

Alert level G
PLAT005_ALERT_5_G No _iucr_refine_instructions_details in CIF ....          ?
PLAT793_ALERT_4_G The Model has Chirality at C8      (Verify) ....          S

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   3 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   2 ALERT level G = General information/check it is not something unexpected

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   3 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check

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S1. Comment

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.

Related literature

For naturally occurring 2-hydroxyindol-3-ones, see: Bhakuni et al. (1991). For intermediates of the 2-hydroxyindol-3-one substructure 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).

S2. Experimental

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%).

S3. Refinement

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 U_iso(H) values of 1.2U_eq(C) [for aromatic-H] or 1.5U_eq(C) [for OH and methyl-H].

Computing details

Data collection: COLLECT (Hooft, 1998); cell refinement: 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).

Figures

	Fig. 1. A view of (I) showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. Association betweem two molecules of (I) via O—H···O hydrogen bonds denoted by dashed lines. Symmetry code: (i) -x + 1, y, -z + 1/2.

2-Hydroxy-2-methyl-1-phenylindolin-3-one

Crystal data

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) Å^3	Prism, green
Z = 8	0.55 × 0.40 × 0.30 mm
F(000) = 1008

Data collection

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

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.116	H-atom parameters constrained
S = 1.04	w = 1/[σ^2(Fo^2) + (0.0545P)^2 + 0.3729P] where P = (Fo^2 + 2Fc^2)/3
2745 reflections	(Δ/σ)max = 0.0001
165 parameters	Δρmax = 0.15 e Å^−3
0 restraints	Δρmin = −0.16 e Å^−3

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	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*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

Geometric parameters (Å, º)

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)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O1^i	0.82	2.12	2.9014 (15)	159

Symmetry code: (i) −x+1, y, −z+1/2.