3-Hydr-oxy-3-nitro-methyl-indolin-2-one.

In the title compound, C(9)H(8)N(2)O(4), the indolin-2-one ring system is substanti-ally planar [maximum deviation = 0.0353 (15) Å]. In the crystal structure, inter-molecular N-H⋯O and O-H⋯O hydrogen bonds are responsible for the formation of a three-dimensional network.

Related literature

For the synthesis of the title compound, see: Imre et al. (2001 ▶); Long et al. (1978 ▶).

Experimental

Crystal data

C9H8N2O4

M = 208.17

Orthorhombic,

a = 10.515 (2) Å

b = 7.3736 (14) Å

c = 23.261 (4) Å

V = 1803.6 (6) Å3

Z = 8

Mo Kα radiation

μ = 0.12 mm−1

T = 293 K

0.21 × 0.18 × 0.15 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2002 ▶) T min = 0.941, T max = 0.961

16322 measured reflections

3807 independent reflections

2098 reflections with I > 2σ(I)

R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.135

S = 1.03

3807 reflections

136 parameters

H-atom parameters constrained

Δρmax = 0.31 e Å−3

Δρmin = −0.21 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/S1600536809039087/rz2364sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809039087/rz2364Isup2.hkl

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

C9H8N2O4	F(000) = 864
Mr = 208.17	Dx = 1.533 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 3122 reflections
a = 10.515 (2) Å	θ = 1.8–34.3°
b = 7.3736 (14) Å	µ = 0.12 mm−1
c = 23.261 (4) Å	T = 293 K
V = 1803.6 (6) Å3	Block, colourless
Z = 8	0.21 × 0.18 × 0.15 mm

Bruker SMART CCD area-detector diffractometer	3807 independent reflections
Radiation source: fine-focus sealed tube	2098 reflections with I > 2σ(I)
graphite	Rint = 0.026
φ and ω scans	θmax = 34.3°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2002)	h = −12→12
Tmin = 0.941, Tmax = 0.961	k = −9→11
16322 measured reflections	l = −28→36

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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.135	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0699P)2 + 0.2564P] where P = (Fo2 + 2Fc2)/3
3807 reflections	(Δ/σ)max = 0.001
136 parameters	Δρmax = 0.31 e Å−3
0 restraints	Δρmin = −0.21 e Å−3

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
N1	0.73793 (10)	0.22536 (14)	0.59575 (4)	0.0345 (2)
H1A	0.8121	0.2684	0.5882	0.041*
C7	0.68870 (11)	0.20320 (15)	0.65183 (5)	0.0313 (3)
C8	0.56744 (11)	0.12898 (14)	0.64887 (5)	0.0294 (2)
C2	0.53211 (11)	0.10262 (14)	0.58677 (5)	0.0287 (2)
O1	0.67140 (9)	0.16574 (14)	0.50346 (4)	0.0452 (3)
C3	0.50087 (12)	0.08802 (17)	0.69844 (5)	0.0374 (3)
H3A	0.4196	0.0386	0.6966	0.045*
C9	0.41221 (12)	0.20580 (16)	0.56828 (5)	0.0354 (3)
H9A	0.4059	0.2048	0.5267	0.043*
H9B	0.3377	0.1453	0.5837	0.043*
C6	0.74609 (13)	0.24268 (17)	0.70380 (5)	0.0396 (3)
H6A	0.8264	0.2951	0.7055	0.048*
N2	0.41524 (12)	0.39586 (15)	0.58894 (5)	0.0470 (3)
C5	0.67832 (15)	0.20049 (18)	0.75336 (6)	0.0450 (3)
H5A	0.7145	0.2253	0.7890	0.054*
C4	0.55872 (14)	0.1227 (2)	0.75123 (5)	0.0448 (3)
H4A	0.5167	0.0934	0.7852	0.054*
O3	0.50508 (14)	0.48843 (17)	0.57450 (9)	0.0904 (5)
O4	0.32881 (14)	0.44827 (19)	0.61941 (6)	0.0776 (4)
C1	0.65394 (11)	0.17044 (15)	0.55545 (5)	0.0317 (3)
O2	0.51621 (8)	−0.08414 (11)	0.57414 (4)	0.0391 (2)
H2A	0.4586	−0.0966	0.5507	0.059*

	U11	U22	U33	U12	U13	U23
N1	0.0244 (5)	0.0384 (5)	0.0408 (5)	−0.0081 (4)	−0.0017 (4)	0.0000 (4)
C7	0.0299 (6)	0.0267 (5)	0.0372 (6)	0.0003 (4)	−0.0040 (4)	0.0000 (4)
C8	0.0259 (6)	0.0268 (5)	0.0353 (5)	0.0019 (4)	−0.0030 (4)	0.0005 (4)
C2	0.0237 (6)	0.0254 (5)	0.0370 (5)	−0.0008 (4)	−0.0022 (4)	−0.0024 (4)
O1	0.0378 (5)	0.0603 (6)	0.0374 (5)	−0.0092 (4)	0.0023 (4)	−0.0040 (4)
C3	0.0303 (6)	0.0389 (6)	0.0431 (6)	0.0043 (5)	0.0031 (5)	0.0048 (5)
C9	0.0276 (6)	0.0352 (6)	0.0435 (6)	0.0037 (5)	−0.0069 (5)	−0.0055 (5)
C6	0.0370 (7)	0.0356 (6)	0.0463 (6)	−0.0006 (5)	−0.0139 (5)	−0.0037 (5)
N2	0.0474 (7)	0.0366 (6)	0.0569 (7)	0.0135 (5)	−0.0168 (5)	−0.0048 (5)
C5	0.0520 (8)	0.0454 (7)	0.0377 (6)	0.0136 (6)	−0.0120 (5)	−0.0052 (5)
C4	0.0476 (8)	0.0503 (7)	0.0364 (6)	0.0154 (6)	0.0037 (5)	0.0044 (5)
O3	0.0736 (9)	0.0354 (6)	0.1620 (17)	−0.0061 (6)	−0.0100 (9)	0.0024 (7)
O4	0.0866 (10)	0.0763 (8)	0.0700 (8)	0.0389 (7)	−0.0037 (7)	−0.0255 (7)
C1	0.0262 (6)	0.0314 (5)	0.0374 (6)	−0.0017 (4)	−0.0008 (4)	−0.0019 (4)
O2	0.0317 (5)	0.0265 (4)	0.0591 (5)	−0.0010 (3)	−0.0098 (4)	−0.0076 (3)

N1—C1	1.3500 (16)	C3—H3A	0.9300
N1—C7	1.4130 (16)	C9—N2	1.4819 (17)
N1—H1A	0.8600	C9—H9A	0.9700
C7—C6	1.3822 (17)	C9—H9B	0.9700
C7—C8	1.3893 (17)	C6—C5	1.390 (2)
C8—C3	1.3823 (17)	C6—H6A	0.9300
C8—C2	1.5042 (15)	N2—O3	1.2129 (19)
C2—O2	1.4180 (13)	N2—O4	1.2155 (18)
C2—C9	1.5340 (16)	C5—C4	1.383 (2)
C2—C1	1.5563 (16)	C5—H5A	0.9300
O1—C1	1.2237 (14)	C4—H4A	0.9300
C3—C4	1.3940 (19)	O2—H2A	0.8200
C1—N1—C7	111.51 (10)	C2—C9—H9A	109.4
C1—N1—H1A	124.2	N2—C9—H9B	109.4
C7—N1—H1A	124.2	C2—C9—H9B	109.4
C6—C7—C8	121.81 (11)	H9A—C9—H9B	108.0
C6—C7—N1	128.55 (11)	C7—C6—C5	117.02 (12)
C8—C7—N1	109.63 (10)	C7—C6—H6A	121.5
C3—C8—C7	120.63 (11)	C5—C6—H6A	121.5
C3—C8—C2	130.37 (11)	O3—N2—O4	124.39 (14)
C7—C8—C2	108.98 (10)	O3—N2—C9	117.33 (13)
O2—C2—C8	110.71 (9)	O4—N2—C9	118.28 (14)
O2—C2—C9	109.07 (9)	C4—C5—C6	121.94 (12)
C8—C2—C9	114.09 (9)	C4—C5—H5A	119.0
O2—C2—C1	108.19 (9)	C6—C5—H5A	119.0
C8—C2—C1	101.81 (9)	C5—C4—C3	120.29 (12)
C9—C2—C1	112.70 (9)	C5—C4—H4A	119.9
C8—C3—C4	118.28 (12)	C3—C4—H4A	119.9
C8—C3—H3A	120.9	O1—C1—N1	126.62 (11)
C4—C3—H3A	120.9	O1—C1—C2	125.24 (10)
N2—C9—C2	111.13 (9)	N1—C1—C2	108.05 (10)
N2—C9—H9A	109.4	C2—O2—H2A	109.5

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O2i	0.86	2.13	2.9849 (14)	171
O2—H2A···O1ii	0.82	1.93	2.7408 (13)	171

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O2i	0.86	2.13	2.9849 (14)	171
O2—H2A⋯O1ii	0.82	1.93	2.7408 (13)	171

Symmetry codes: (i) ; (ii) .