1-Octylindoline-2,3-dione.

In the title compound, C16H21NO2, the indoline ring and the two ketone O atoms are approximately coplanar, the largest deviation from the mean plane being 0.063 (2) Å. The mean plane through the fused ring system is nearly perpendicular to the mean plane passing through the 1-octyl chain [dihedral angle = 77.53 (17)°]. In the crystal, mol-ecules are linked by C-H⋯O hydrogen bonds, forming a three-dimensional network.

Related literature

For the biological activity of indoline derivatives, see: Bhrigu et al. (2010 ▶); Malhotra et al. (2011 ▶); Da Silva et al. (2001 ▶); Ramachandran (2011 ▶); Smitha et al. (2008 ▶). For the structure of a related compound, see: Mamari et al. (2010 ▶).

Experimental

Crystal data

C16H21NO2

M = 259.34

Monoclinic,

a = 20.266 (4) Å

b = 4.6925 (1) Å

c = 15.7807 (11) Å

β = 108.941 (18)°

V = 1419.5 (3) Å3

Z = 4

Cu Kα radiation

μ = 0.63 mm−1

T = 123 K

0.31 × 0.07 × 0.04 mm

Data collection

Oxford Diffraction SuperNova (single source at offset, Atlas) diffractometer

Absorption correction: analytical [CrysAlis PRO (Oxford Diffraction, 2012 ▶); analytical numeric absorption correction using a multi-faceted crystal model (Clark & Reid, 1995 ▶)] T min = 0.899, T max = 0.979

13541 measured reflections

2811 independent reflections

2462 reflections with I > 2σ(I)

R int = 0.029

Refinement

R[F 2 > 2σ(F 2)] = 0.057

wR(F 2) = 0.167

S = 1.18

2811 reflections

172 parameters

H-atom parameters constrained

Δρmax = 0.49 e Å−3

Δρmin = −0.22 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2012 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: WinGX (Farrugia, 2012 ▶); software used to prepare material for publication: WinGX (Farrugia, 2012 ▶) and publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) I. DOI: 10.1107/S1600536813031383/rz5095sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813031383/rz5095Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813031383/rz5095Isup3.cml

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

C16H21NO2	F(000) = 560
Mr = 259.34	Dx = 1.214 Mg m−3
Monoclinic, P21/c	Melting point: 317 K
Hall symbol: -P 2ybc	Cu Kα radiation, λ = 1.5418 Å
a = 20.266 (4) Å	Cell parameters from 5321 reflections
b = 4.6925 (1) Å	θ = 3.0–73.5°
c = 15.7807 (11) Å	µ = 0.63 mm−1
β = 108.941 (18)°	T = 123 K
V = 1419.5 (3) Å3	Plate, orange
Z = 4	0.31 × 0.07 × 0.04 mm

Oxford Diffraction SuperNova (single source at offset, Atlas) diffractometer	2811 independent reflections
Radiation source: SuperNova (Cu) X-ray Source	2462 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.029
Detector resolution: 20.7092 pixels mm-1	θmax = 73.7°, θmin = 4.6°
ω scans	h = −24→25
Absorption correction: analytical [CrysAlis PRO (Oxford Diffraction, 2012); analytical numeric absorption correction using a multi-faceted crystal model (Clark & Reid, 1995)]	k = −5→5
Tmin = 0.899, Tmax = 0.979	l = −17→19
13541 measured reflections

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)] = 0.057	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.167	H-atom parameters constrained
S = 1.18	w = 1/[σ2(Fo2) + (0.0633P)2 + 1.1901P] where P = (Fo2 + 2Fc2)/3
2811 reflections	(Δ/σ)max < 0.001
172 parameters	Δρmax = 0.49 e Å−3
0 restraints	Δρmin = −0.22 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 > 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	0.33354 (9)	0.7667 (4)	0.34657 (10)	0.0397 (4)
O2	0.44511 (8)	1.1900 (4)	0.42454 (10)	0.0385 (4)
N1	0.32574 (9)	0.7836 (4)	0.48939 (11)	0.0272 (4)
C1	0.35221 (11)	0.8574 (5)	0.42319 (14)	0.0299 (5)
C2	0.40999 (10)	1.0835 (5)	0.46468 (14)	0.0288 (5)
C3	0.40798 (10)	1.1295 (4)	0.55543 (13)	0.0258 (4)
C4	0.44509 (10)	1.3124 (5)	0.62281 (15)	0.0296 (5)
H4	0.4791	1.4325	0.6148	0.036*
C5	0.43015 (11)	1.3116 (5)	0.70275 (14)	0.0308 (5)
H5	0.4540	1.4343	0.7488	0.037*
C6	0.37992 (11)	1.1290 (5)	0.71428 (13)	0.0290 (5)
H6	0.3710	1.1310	0.7685	0.035*
C7	0.34230 (10)	0.9420 (5)	0.64691 (13)	0.0272 (4)
H7	0.3089	0.8196	0.6553	0.033*
C8	0.35685 (9)	0.9471 (4)	0.56786 (13)	0.0241 (4)
C9	0.26652 (10)	0.5930 (5)	0.47581 (15)	0.0303 (5)
H9A	0.2732	0.4819	0.5298	0.036*
H9B	0.2645	0.4618	0.4275	0.036*
C10	0.19768 (10)	0.7542 (5)	0.45315 (15)	0.0300 (5)
H10A	0.1940	0.8837	0.4039	0.036*
H10B	0.1976	0.8674	0.5045	0.036*
C11	0.13437 (10)	0.5572 (5)	0.42731 (15)	0.0305 (5)
H11A	0.1382	0.4262	0.4763	0.037*
H11B	0.1341	0.4455	0.3754	0.037*
C12	0.06565 (10)	0.7207 (5)	0.40574 (15)	0.0311 (5)
H12A	0.0651	0.8230	0.4589	0.037*
H12B	0.0635	0.8605	0.3597	0.037*
C13	0.00107 (10)	0.5314 (5)	0.37394 (15)	0.0317 (5)
H13A	0.0014	0.4298	0.3205	0.038*
H13B	0.0031	0.3912	0.4199	0.038*
C14	−0.06690 (11)	0.6980 (5)	0.35310 (15)	0.0327 (5)
H14A	−0.0683	0.8412	0.3082	0.039*
H14B	−0.0675	0.7962	0.4069	0.039*
C15	−0.13189 (11)	0.5123 (5)	0.31923 (16)	0.0358 (5)
H15A	−0.1306	0.3683	0.3638	0.043*
H15B	−0.1317	0.4154	0.2650	0.043*
C16	−0.19929 (12)	0.6838 (6)	0.29952 (18)	0.0429 (6)
H16A	−0.2386	0.5578	0.2788	0.064*
H16B	−0.2015	0.8234	0.2542	0.064*
H16C	−0.2001	0.7778	0.3532	0.064*

	U11	U22	U33	U12	U13	U23
O1	0.0396 (9)	0.0494 (10)	0.0293 (8)	0.0081 (7)	0.0102 (7)	−0.0051 (7)
O2	0.0303 (8)	0.0559 (11)	0.0335 (8)	0.0040 (7)	0.0160 (7)	0.0132 (7)
N1	0.0222 (8)	0.0314 (9)	0.0271 (9)	0.0000 (7)	0.0067 (7)	−0.0028 (7)
C1	0.0265 (10)	0.0372 (12)	0.0262 (10)	0.0098 (8)	0.0087 (8)	0.0014 (8)
C2	0.0224 (9)	0.0349 (11)	0.0297 (10)	0.0088 (8)	0.0092 (8)	0.0086 (9)
C3	0.0225 (9)	0.0285 (10)	0.0275 (10)	0.0050 (7)	0.0096 (8)	0.0072 (8)
C4	0.0207 (9)	0.0307 (11)	0.0364 (11)	−0.0008 (8)	0.0078 (8)	0.0049 (9)
C5	0.0267 (10)	0.0319 (11)	0.0312 (11)	0.0000 (8)	0.0059 (8)	−0.0013 (8)
C6	0.0275 (10)	0.0353 (11)	0.0243 (10)	0.0047 (8)	0.0084 (8)	0.0026 (8)
C7	0.0240 (9)	0.0306 (11)	0.0286 (10)	0.0001 (8)	0.0107 (8)	0.0031 (8)
C8	0.0188 (9)	0.0257 (10)	0.0263 (9)	0.0040 (7)	0.0053 (7)	0.0011 (8)
C9	0.0250 (10)	0.0284 (11)	0.0350 (11)	−0.0012 (8)	0.0064 (8)	−0.0031 (8)
C10	0.0247 (10)	0.0299 (11)	0.0340 (11)	0.0014 (8)	0.0074 (8)	−0.0014 (8)
C11	0.0238 (10)	0.0311 (11)	0.0345 (11)	0.0004 (8)	0.0063 (8)	−0.0026 (9)
C12	0.0236 (10)	0.0324 (11)	0.0353 (11)	0.0011 (8)	0.0067 (8)	−0.0013 (9)
C13	0.0253 (10)	0.0337 (12)	0.0347 (11)	0.0000 (8)	0.0079 (8)	−0.0023 (9)
C14	0.0256 (11)	0.0365 (12)	0.0344 (11)	0.0004 (9)	0.0075 (9)	−0.0005 (9)
C15	0.0271 (11)	0.0404 (13)	0.0388 (12)	−0.0014 (9)	0.0092 (9)	−0.0039 (10)
C16	0.0244 (11)	0.0546 (15)	0.0462 (14)	−0.0006 (10)	0.0069 (10)	−0.0003 (12)

O1—C1	1.220 (3)	C10—H10A	0.9700
O2—C2	1.204 (3)	C10—H10B	0.9700
N1—C1	1.365 (3)	C11—C12	1.528 (3)
N1—C8	1.419 (3)	C11—H11A	0.9700
N1—C9	1.456 (3)	C11—H11B	0.9700
C1—C2	1.558 (3)	C12—C13	1.526 (3)
C2—C3	1.462 (3)	C12—H12A	0.9700
C3—C4	1.383 (3)	C12—H12B	0.9700
C3—C8	1.406 (3)	C13—C14	1.524 (3)
C4—C5	1.390 (3)	C13—H13A	0.9700
C4—H4	0.9300	C13—H13B	0.9700
C5—C6	1.387 (3)	C14—C15	1.524 (3)
C5—H5	0.9300	C14—H14A	0.9700
C6—C7	1.398 (3)	C14—H14B	0.9700
C6—H6	0.9300	C15—C16	1.528 (3)
C7—C8	1.372 (3)	C15—H15A	0.9700
C7—H7	0.9300	C15—H15B	0.9700
C9—C10	1.524 (3)	C16—H16A	0.9600
C9—H9A	0.9700	C16—H16B	0.9600
C9—H9B	0.9700	C16—H16C	0.9600
C10—C11	1.526 (3)
C1—N1—C8	110.93 (17)	H10A—C10—H10B	107.8
C1—N1—C9	123.59 (18)	C10—C11—C12	112.44 (18)
C8—N1—C9	124.91 (17)	C10—C11—H11A	109.1
O1—C1—N1	126.7 (2)	C12—C11—H11A	109.1
O1—C1—C2	127.1 (2)	C10—C11—H11B	109.1
N1—C1—C2	106.24 (17)	C12—C11—H11B	109.1
O2—C2—C3	131.6 (2)	H11A—C11—H11B	107.8
O2—C2—C1	123.6 (2)	C13—C12—C11	113.79 (18)
C3—C2—C1	104.83 (16)	C13—C12—H12A	108.8
C4—C3—C8	120.78 (18)	C11—C12—H12A	108.8
C4—C3—C2	131.56 (19)	C13—C12—H12B	108.8
C8—C3—C2	107.65 (18)	C11—C12—H12B	108.8
C3—C4—C5	118.16 (19)	H12A—C12—H12B	107.7
C3—C4—H4	120.9	C14—C13—C12	113.04 (18)
C5—C4—H4	120.9	C14—C13—H13A	109.0
C6—C5—C4	120.4 (2)	C12—C13—H13A	109.0
C6—C5—H5	119.8	C14—C13—H13B	109.0
C4—C5—H5	119.8	C12—C13—H13B	109.0
C5—C6—C7	122.01 (19)	H13A—C13—H13B	107.8
C5—C6—H6	119.0	C13—C14—C15	113.60 (19)
C7—C6—H6	119.0	C13—C14—H14A	108.8
C8—C7—C6	117.09 (19)	C15—C14—H14A	108.8
C8—C7—H7	121.5	C13—C14—H14B	108.8
C6—C7—H7	121.5	C15—C14—H14B	108.8
C7—C8—C3	121.54 (19)	H14A—C14—H14B	107.7
C7—C8—N1	128.20 (18)	C14—C15—C16	112.6 (2)
C3—C8—N1	110.25 (17)	C14—C15—H15A	109.1
N1—C9—C10	112.20 (17)	C16—C15—H15A	109.1
N1—C9—H9A	109.2	C14—C15—H15B	109.1
C10—C9—H9A	109.2	C16—C15—H15B	109.1
N1—C9—H9B	109.2	H15A—C15—H15B	107.8
C10—C9—H9B	109.2	C15—C16—H16A	109.5
H9A—C9—H9B	107.9	C15—C16—H16B	109.5
C9—C10—C11	112.85 (17)	H16A—C16—H16B	109.5
C9—C10—H10A	109.0	C15—C16—H16C	109.5
C11—C10—H10A	109.0	H16A—C16—H16C	109.5
C9—C10—H10B	109.0	H16B—C16—H16C	109.5
C11—C10—H10B	109.0
C8—N1—C1—O1	−175.8 (2)	C6—C7—C8—N1	−179.05 (19)
C9—N1—C1—O1	−4.1 (3)	C4—C3—C8—C7	−0.5 (3)
C8—N1—C1—C2	3.3 (2)	C2—C3—C8—C7	−179.61 (18)
C9—N1—C1—C2	174.96 (17)	C4—C3—C8—N1	179.39 (18)
O1—C1—C2—O2	−2.5 (3)	C2—C3—C8—N1	0.3 (2)
N1—C1—C2—O2	178.42 (19)	C1—N1—C8—C7	177.49 (19)
O1—C1—C2—C3	176.1 (2)	C9—N1—C8—C7	5.9 (3)
N1—C1—C2—C3	−3.0 (2)	C1—N1—C8—C3	−2.4 (2)
O2—C2—C3—C4	1.1 (4)	C9—N1—C8—C3	−173.93 (18)
C1—C2—C3—C4	−177.4 (2)	C1—N1—C9—C10	−93.2 (2)
O2—C2—C3—C8	−180.0 (2)	C8—N1—C9—C10	77.3 (2)
C1—C2—C3—C8	1.6 (2)	N1—C9—C10—C11	172.83 (17)
C8—C3—C4—C5	−0.3 (3)	C9—C10—C11—C12	179.35 (18)
C2—C3—C4—C5	178.5 (2)	C10—C11—C12—C13	176.35 (18)
C3—C4—C5—C6	0.8 (3)	C11—C12—C13—C14	179.79 (18)
C4—C5—C6—C7	−0.5 (3)	C12—C13—C14—C15	178.69 (18)
C5—C6—C7—C8	−0.3 (3)	C13—C14—C15—C16	179.56 (19)
C6—C7—C8—C3	0.8 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···O1i	0.93	2.49	3.156 (3)	129
C6—H6···O2ii	0.93	2.57	3.260 (3)	131
C4—H4···O2iii	0.93	2.55	3.470 (3)	170

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6⋯O1i	0.93	2.49	3.156 (3)	129
C6—H6⋯O2ii	0.93	2.57	3.260 (3)	131
C4—H4⋯O2iii	0.93	2.55	3.470 (3)	170

Symmetry codes: (i) ; (ii) ; (iii) .