2-Hy-droxy-2-methyl-1-phenyl-indolin-3-one.

In the title compound, C(15)H(13)NO(2), 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 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 ▶).

Experimental

Crystal data

C15H13NO2

M = 239.26

Orthorhombic,

a = 17.0146 (4) Å

b = 9.2193 (2) Å

c = 15.3843 (4) Å

V = 2413.22 (10) Å3

Z = 8

Mo Kα radiation

μ = 0.09 mm−1

T = 295 K

0.55 × 0.40 × 0.30 mm

Data collection

Nonius KappaCCD area-detector diffractometer

Absorption correction: multi-scan (SCALEPACK; Otwinowski & Minor, 1997 ▶) T min = 0.953, T max = 0.974

5144 measured reflections

2745 independent reflections

1890 reflections with I > 2σ(I)

R int = 0.022

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.116

S = 1.04

2745 reflections

165 parameters

H-atom parameters constrained

Δρmax = 0.15 e Å−3

Δρmin = −0.16 e Å−3

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

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811045302/tk5007sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811045302/tk5007Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811045302/tk5007Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

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	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

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

Table 1

Hydrogen-bond geometry (Å, °)

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) .