Spiro-[cyclo-propane-1,3'-indolin]-2'-one.

In the title mol-ecule, C(10)H(9)NO, the dihedral angle between the mean plane of the cyclo-propane ring and the essentially planar [maximum deviation = 0.032 (2) Å] indole ring system is 87.65 (17)°. In the crystal, inter-molecular N-H⋯O hydrogen bonds link mol-ecules into one-dimensional chains along [100].

Related literature

For the applications of indoline-2-one and its derivatives, see: Wang et al. (2011 ▶); Ji et al. (2010 ▶). For a related structure, see: Yong et al. (2007 ▶).

Experimental

Crystal data

C10H9NO

M = 159.18

Orthorhombic,

a = 7.4348 (6) Å

b = 14.0589 (11) Å

c = 15.6401 (16) Å

V = 1634.8 (2) Å3

Z = 8

Mo Kα radiation

μ = 0.09 mm−1

T = 298 K

0.50 × 0.45 × 0.42 mm

Data collection

Bruker SMART CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.959, T max = 0.965

7724 measured reflections

1442 independent reflections

1024 reflections with I > 2σ(I)

R int = 0.033

Refinement

R[F 2 > 2σ(F 2)] = 0.035

wR(F 2) = 0.106

S = 1.09

1442 reflections

110 parameters

H-atom parameters constrained

Δρmax = 0.15 e Å−3

Δρmin = −0.11 e Å−3

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811034167/lh5317sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811034167/lh5317Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811034167/lh5317Isup3.cml

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

C10H9NO	F(000) = 672
Mr = 159.18	Dx = 1.294 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 2492 reflections
a = 7.4348 (6) Å	θ = 2.9–26.3°
b = 14.0589 (11) Å	µ = 0.09 mm−1
c = 15.6401 (16) Å	T = 298 K
V = 1634.8 (2) Å3	Block, colorless
Z = 8	0.50 × 0.45 × 0.42 mm

Bruker SMART CCD diffractometer	1442 independent reflections
Radiation source: fine-focus sealed tube	1024 reflections with I > 2σ(I)
graphite	Rint = 0.033
φ and ω scans	θmax = 25.0°, θmin = 2.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −8→5
Tmin = 0.959, Tmax = 0.965	k = −16→16
7724 measured reflections	l = −18→18

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)] = 0.035	H-atom parameters constrained
wR(F2) = 0.106	w = 1/[σ2(Fo2) + (0.039P)2 + 0.514P] where P = (Fo2 + 2Fc2)/3
S = 1.09	(Δ/σ)max < 0.001
1442 reflections	Δρmax = 0.15 e Å−3
110 parameters	Δρmin = −0.11 e Å−3
0 restraints	Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.029 (3)

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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	0.59216 (19)	0.65349 (11)	0.54786 (9)	0.0505 (4)
H1	0.6712	0.6798	0.5154	0.061*
O1	0.38643 (18)	0.77529 (9)	0.55038 (10)	0.0683 (5)
C1	0.4374 (2)	0.69564 (13)	0.57235 (12)	0.0485 (5)
C2	0.3453 (2)	0.62839 (13)	0.63111 (11)	0.0457 (5)
C3	0.4605 (2)	0.54356 (12)	0.63342 (11)	0.0445 (5)
C4	0.6083 (2)	0.56211 (12)	0.58160 (11)	0.0440 (4)
C5	0.7419 (3)	0.49602 (16)	0.56891 (13)	0.0617 (6)
H5	0.8403	0.5091	0.5341	0.074*
C6	0.7245 (4)	0.40906 (16)	0.60998 (17)	0.0771 (7)
H6	0.8131	0.3630	0.6029	0.092*
C7	0.5787 (4)	0.38995 (16)	0.66098 (17)	0.0797 (8)
H7	0.5697	0.3311	0.6877	0.096*
C8	0.4454 (3)	0.45660 (14)	0.67318 (14)	0.0651 (6)
H8	0.3468	0.4431	0.7077	0.078*
C9	0.1417 (2)	0.62741 (16)	0.63580 (14)	0.0625 (6)
H9A	0.0765	0.6704	0.5985	0.075*
H9B	0.0831	0.5668	0.6456	0.075*
C10	0.2446 (3)	0.66937 (17)	0.70712 (13)	0.0663 (6)
H10A	0.2490	0.6343	0.7605	0.080*
H10B	0.2424	0.7380	0.7134	0.080*

	U11	U22	U33	U12	U13	U23
N1	0.0398 (8)	0.0637 (10)	0.0481 (9)	−0.0077 (7)	0.0010 (7)	0.0114 (7)
O1	0.0568 (9)	0.0588 (9)	0.0892 (11)	−0.0017 (7)	−0.0157 (8)	0.0200 (8)
C1	0.0412 (10)	0.0541 (11)	0.0502 (11)	−0.0046 (8)	−0.0123 (8)	0.0059 (9)
C2	0.0391 (10)	0.0552 (11)	0.0429 (10)	−0.0060 (8)	−0.0023 (8)	0.0017 (8)
C3	0.0453 (10)	0.0490 (10)	0.0394 (10)	−0.0077 (8)	−0.0089 (8)	0.0019 (8)
C4	0.0402 (9)	0.0532 (10)	0.0386 (9)	−0.0024 (8)	−0.0092 (8)	−0.0033 (8)
C5	0.0459 (11)	0.0789 (14)	0.0602 (13)	0.0048 (10)	−0.0129 (9)	−0.0202 (11)
C6	0.0754 (16)	0.0609 (14)	0.0949 (18)	0.0185 (12)	−0.0395 (15)	−0.0222 (13)
C7	0.0890 (19)	0.0562 (13)	0.0939 (18)	−0.0028 (13)	−0.0356 (16)	0.0110 (12)
C8	0.0685 (14)	0.0618 (13)	0.0651 (14)	−0.0127 (11)	−0.0119 (11)	0.0146 (11)
C9	0.0403 (11)	0.0805 (14)	0.0668 (14)	−0.0067 (9)	0.0014 (10)	0.0049 (11)
C10	0.0555 (12)	0.0875 (15)	0.0558 (12)	0.0020 (11)	0.0062 (10)	−0.0075 (11)

N1—C1	1.350 (2)	C5—H5	0.9300
N1—C4	1.394 (2)	C6—C7	1.373 (4)
N1—H1	0.8600	C6—H6	0.9300
O1—C1	1.231 (2)	C7—C8	1.377 (3)
C1—C2	1.486 (2)	C7—H7	0.9300
C2—C3	1.469 (2)	C8—H8	0.9300
C2—C9	1.515 (3)	C9—C10	1.476 (3)
C2—C10	1.518 (3)	C9—H9A	0.9700
C3—C8	1.376 (2)	C9—H9B	0.9700
C3—C4	1.390 (2)	C10—H10A	0.9700
C4—C5	1.375 (3)	C10—H10B	0.9700
C5—C6	1.387 (3)
C1—N1—C4	111.75 (15)	C7—C6—C5	121.0 (2)
C1—N1—H1	124.1	C7—C6—H6	119.5
C4—N1—H1	124.1	C5—C6—H6	119.5
O1—C1—N1	125.62 (18)	C6—C7—C8	121.1 (2)
O1—C1—C2	127.56 (18)	C6—C7—H7	119.5
N1—C1—C2	106.81 (15)	C8—C7—H7	119.5
C3—C2—C1	105.25 (15)	C3—C8—C7	118.9 (2)
C3—C2—C9	125.03 (17)	C3—C8—H8	120.6
C1—C2—C9	119.74 (16)	C7—C8—H8	120.6
C3—C2—C10	125.19 (17)	C10—C9—C2	60.99 (13)
C1—C2—C10	118.04 (16)	C10—C9—H9A	117.7
C9—C2—C10	58.22 (13)	C2—C9—H9A	117.7
C8—C3—C4	119.65 (18)	C10—C9—H9B	117.7
C8—C3—C2	133.21 (18)	C2—C9—H9B	117.7
C4—C3—C2	107.12 (15)	H9A—C9—H9B	114.8
C5—C4—C3	121.91 (18)	C9—C10—C2	60.79 (13)
C5—C4—N1	129.09 (18)	C9—C10—H10A	117.7
C3—C4—N1	109.00 (15)	C2—C10—H10A	117.7
C4—C5—C6	117.5 (2)	C9—C10—H10B	117.7
C4—C5—H5	121.3	C2—C10—H10B	117.7
C6—C5—H5	121.3	H10A—C10—H10B	114.8
C4—N1—C1—O1	−178.13 (17)	C8—C3—C4—N1	179.15 (16)
C4—N1—C1—C2	2.87 (19)	C2—C3—C4—N1	0.42 (18)
O1—C1—C2—C3	178.55 (18)	C1—N1—C4—C5	177.34 (17)
N1—C1—C2—C3	−2.47 (18)	C1—N1—C4—C3	−2.14 (19)
O1—C1—C2—C9	31.3 (3)	C3—C4—C5—C6	0.0 (3)
N1—C1—C2—C9	−149.71 (17)	N1—C4—C5—C6	−179.43 (17)
O1—C1—C2—C10	−36.2 (3)	C4—C5—C6—C7	0.3 (3)
N1—C1—C2—C10	142.81 (16)	C5—C6—C7—C8	−0.2 (3)
C1—C2—C3—C8	−177.26 (19)	C4—C3—C8—C7	0.5 (3)
C9—C2—C3—C8	−32.3 (3)	C2—C3—C8—C7	178.80 (19)
C10—C2—C3—C8	40.7 (3)	C6—C7—C8—C3	−0.2 (3)
C1—C2—C3—C4	1.23 (18)	C3—C2—C9—C10	113.2 (2)
C9—C2—C3—C4	146.22 (18)	C1—C2—C9—C10	−106.4 (2)
C10—C2—C3—C4	−140.81 (17)	C3—C2—C10—C9	−112.9 (2)
C8—C3—C4—C5	−0.4 (3)	C1—C2—C10—C9	109.34 (19)
C2—C3—C4—C5	−179.11 (16)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1i	0.86	2.00	2.855 (2)	170

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1i	0.86	2.00	2.855 (2)	170

Symmetry code: (i) .