3-Hydr-oxy-3-[(2-methyl-propano-yl)meth-yl]indolin-2-one.

The title compound, C(13)H(15)NO(3), was synthesized by the Aldol reaction of isatin and 3-methyl-butan-2-one refluxing in methanol catalyzed by dimethyl-amine. The packing of the mol-ecules in the crystal structure features inter-molecular N-H⋯O and O-H⋯O hydrogen bonds.

Related literature

For related structures, see: Garden et al. (2002 ▶); Li, et al. (2008 ▶). For the bioactivity of derivatives, see: Glover et al. (1988 ▶); Marti & Carreira (2003 ▶); Pandeya et al. (2000 ▶); Sun et al. (1998 ▶); Teitz et al. (1994 ▶).

Experimental

Crystal data

C13H15NO3

M = 233.26

Monoclinic,

a = 11.885 (2) Å

b = 5.9244 (12) Å

c = 16.695 (3) Å

β = 98.60 (3)°

V = 1162.3 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 293 K

0.23 × 0.18 × 0.15 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2005 ▶) T min = 0.945, T max = 0.985

8623 measured reflections

2577 independent reflections

1902 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.161

S = 1.09

2577 reflections

155 parameters

H-atom parameters constrained

Δρmax = 0.24 e Å−3

Δρmin = −0.22 e Å−3

Data collection: SMART (Bruker, 2002 ▶); cell refinement: SAINT (Bruker, 2002 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and DIAMOND (Brandenburg, 1999 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809024611/ww2134sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809024611/ww2134Isup2.hkl

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

C13H15NO3	F(000) = 496
Mr = 233.26	Dx = 1.333 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3113 reflections
a = 11.885 (2) Å	θ = 1.9–27.4°
b = 5.9244 (12) Å	µ = 0.10 mm−1
c = 16.695 (3) Å	T = 293 K
β = 98.60 (3)°	Block, colorless
V = 1162.3 (5) Å3	0.23 × 0.18 × 0.15 mm
Z = 4

Bruker SMART CCD area-detector diffractometer	2577 independent reflections
Radiation source: fine-focus sealed tube	1902 reflections with I > 2σ(I)
graphite	Rint = 0.028
φ and ω scans	θmax = 27.5°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 2005)	h = −15→14
Tmin = 0.945, Tmax = 0.985	k = −7→7
8623 measured reflections	l = −21→15

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)] = 0.045	H-atom parameters constrained
wR(F2) = 0.161	w = 1/[σ2(Fo2) + (0.0562P)2 + 0.2707P] where P = (Fo2 + 2Fc2)/3
S = 1.09	(Δ/σ)max < 0.001
2577 reflections	Δρmax = 0.24 e Å−3
155 parameters	Δρmin = −0.22 e Å−3
0 restraints	Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4'
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.018 (4)

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
O2	0.57929 (9)	0.14669 (16)	0.55228 (6)	0.0335 (3)
H2A	0.5183	0.2128	0.5411	0.050*
O1	0.62325 (9)	0.59992 (19)	0.48205 (6)	0.0368 (3)
N1	0.60709 (11)	0.6720 (2)	0.61556 (8)	0.0324 (3)
H1A	0.5830	0.8088	0.6103	0.039*
O3	0.87069 (11)	0.5445 (2)	0.61665 (9)	0.0542 (4)
C1	0.63221 (12)	0.5435 (2)	0.55343 (9)	0.0292 (4)
C8	0.66420 (12)	0.3373 (2)	0.67659 (9)	0.0278 (4)
C9	0.77543 (13)	0.2149 (3)	0.56337 (10)	0.0320 (4)
H9A	0.7868	0.0611	0.5829	0.038*
H9B	0.7679	0.2105	0.5047	0.038*
C10	0.87990 (14)	0.3519 (3)	0.59554 (10)	0.0347 (4)
C7	0.62536 (13)	0.5539 (2)	0.69000 (9)	0.0289 (4)
C2	0.66509 (12)	0.3034 (2)	0.58702 (9)	0.0276 (4)
C3	0.69101 (13)	0.1899 (3)	0.74041 (9)	0.0322 (4)
H3A	0.7185	0.0462	0.7320	0.039*
C6	0.61006 (14)	0.6260 (3)	0.76617 (10)	0.0351 (4)
H6A	0.5832	0.7702	0.7746	0.042*
C4	0.67614 (14)	0.2602 (3)	0.81790 (10)	0.0383 (4)
H4A	0.6931	0.1621	0.8615	0.046*
C5	0.63660 (14)	0.4736 (3)	0.83018 (10)	0.0381 (4)
H5A	0.6273	0.5176	0.8823	0.046*
C11	0.99369 (15)	0.2365 (3)	0.59805 (12)	0.0500 (5)
H11A	0.9932	0.1539	0.5471	0.060*
C12	1.0100 (2)	0.0663 (4)	0.66754 (18)	0.0843 (9)
H12A	0.9472	−0.0375	0.6614	0.126*
H12B	1.0133	0.1446	0.7182	0.126*
H12C	1.0796	−0.0153	0.6667	0.126*
C13	1.09104 (19)	0.4058 (5)	0.60623 (16)	0.0752 (7)
H13A	1.0797	0.5089	0.5614	0.113*
H13B	1.1617	0.3271	0.6065	0.113*
H13C	1.0931	0.4880	0.6560	0.113*

	U11	U22	U33	U12	U13	U23
O2	0.0286 (6)	0.0262 (6)	0.0431 (7)	−0.0024 (4)	−0.0035 (5)	−0.0012 (4)
O1	0.0390 (7)	0.0385 (7)	0.0323 (6)	0.0007 (5)	0.0031 (5)	0.0073 (5)
N1	0.0381 (8)	0.0242 (6)	0.0349 (8)	0.0044 (5)	0.0053 (6)	0.0016 (5)
O3	0.0401 (8)	0.0400 (8)	0.0817 (10)	−0.0055 (5)	0.0068 (7)	−0.0124 (7)
C1	0.0247 (8)	0.0269 (8)	0.0353 (9)	−0.0018 (6)	0.0021 (6)	0.0021 (6)
C8	0.0247 (8)	0.0271 (8)	0.0317 (8)	−0.0010 (6)	0.0044 (6)	0.0004 (6)
C9	0.0290 (8)	0.0312 (8)	0.0352 (8)	0.0019 (6)	0.0025 (6)	−0.0032 (6)
C10	0.0325 (9)	0.0390 (9)	0.0334 (9)	−0.0020 (7)	0.0074 (7)	−0.0007 (7)
C7	0.0252 (8)	0.0283 (8)	0.0332 (8)	−0.0003 (6)	0.0041 (6)	0.0025 (6)
C2	0.0263 (8)	0.0253 (8)	0.0300 (8)	−0.0016 (6)	0.0002 (6)	−0.0015 (6)
C3	0.0324 (9)	0.0277 (8)	0.0360 (9)	0.0022 (6)	0.0034 (7)	0.0036 (6)
C6	0.0346 (9)	0.0301 (9)	0.0415 (9)	0.0009 (6)	0.0085 (7)	−0.0054 (7)
C4	0.0377 (10)	0.0429 (10)	0.0333 (9)	−0.0001 (7)	0.0022 (7)	0.0066 (7)
C5	0.0340 (9)	0.0512 (11)	0.0298 (8)	−0.0023 (7)	0.0071 (6)	−0.0045 (7)
C11	0.0313 (10)	0.0610 (12)	0.0566 (12)	0.0022 (8)	0.0033 (8)	−0.0117 (10)
C12	0.0569 (15)	0.0593 (14)	0.127 (2)	0.0053 (11)	−0.0164 (14)	0.0254 (15)
C13	0.0335 (12)	0.1033 (19)	0.0886 (18)	−0.0095 (12)	0.0084 (11)	0.0082 (15)

O2—C2	1.4356 (16)	C3—C4	1.395 (2)
O2—H2A	0.8200	C3—H3A	0.9300
O1—C1	1.2270 (18)	C6—C5	1.399 (2)
N1—C1	1.355 (2)	C6—H6A	0.9300
N1—C7	1.4144 (19)	C4—C5	1.375 (3)
N1—H1A	0.8600	C4—H4A	0.9300
O3—C10	1.204 (2)	C5—H5A	0.9300
C1—C2	1.557 (2)	C11—C13	1.522 (3)
C8—C3	1.378 (2)	C11—C12	1.527 (3)
C8—C7	1.393 (2)	C11—H11A	0.9800
C8—C2	1.510 (2)	C12—H12A	0.9600
C9—C10	1.513 (2)	C12—H12B	0.9600
C9—C2	1.518 (2)	C12—H12C	0.9600
C9—H9A	0.9700	C13—H13A	0.9600
C9—H9B	0.9700	C13—H13B	0.9600
C10—C11	1.511 (2)	C13—H13C	0.9600
C7—C6	1.379 (2)
C2—O2—H2A	109.5	C8—C3—H3A	120.6
C1—N1—C7	111.85 (12)	C4—C3—H3A	120.6
C1—N1—H1A	124.1	C7—C6—C5	117.29 (15)
C7—N1—H1A	124.1	C7—C6—H6A	121.4
O1—C1—N1	126.39 (14)	C5—C6—H6A	121.4
O1—C1—C2	125.40 (14)	C5—C4—C3	120.42 (15)
N1—C1—C2	108.04 (13)	C5—C4—H4A	119.8
C3—C8—C7	120.23 (14)	C3—C4—H4A	119.8
C3—C8—C2	130.26 (14)	C4—C5—C6	121.53 (15)
C7—C8—C2	109.47 (12)	C4—C5—H5A	119.2
C10—C9—C2	114.65 (13)	C6—C5—H5A	119.2
C10—C9—H9A	108.6	C13—C11—C10	111.69 (16)
C2—C9—H9A	108.6	C13—C11—C12	111.02 (18)
C10—C9—H9B	108.6	C10—C11—C12	109.35 (17)
C2—C9—H9B	108.6	C13—C11—H11A	108.2
H9A—C9—H9B	107.6	C10—C11—H11A	108.2
O3—C10—C11	122.77 (15)	C12—C11—H11A	108.2
O3—C10—C9	120.45 (15)	C11—C12—H12A	109.5
C11—C10—C9	116.77 (14)	C11—C12—H12B	109.5
C6—C7—C8	121.75 (14)	H12A—C12—H12B	109.5
C6—C7—N1	129.26 (14)	C11—C12—H12C	109.5
C8—C7—N1	108.99 (13)	H12A—C12—H12C	109.5
O2—C2—C8	112.10 (12)	H12B—C12—H12C	109.5
O2—C2—C9	105.10 (11)	C11—C13—H13A	109.5
C8—C2—C9	115.95 (12)	C11—C13—H13B	109.5
O2—C2—C1	108.68 (11)	H13A—C13—H13B	109.5
C8—C2—C1	101.33 (11)	C11—C13—H13C	109.5
C9—C2—C1	113.69 (13)	H13A—C13—H13C	109.5
C8—C3—C4	118.76 (15)	H13B—C13—H13C	109.5

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O2i	0.86	2.22	3.0049 (18)	151
O2—H2A···O1ii	0.82	2.00	2.8220 (17)	175

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O2i	0.86	2.22	3.0049 (18)	151
O2—H2A⋯O1ii	0.82	2.00	2.8220 (17)	175

Symmetry codes: (i) ; (ii) .