1-Do-decyl-indoline-2,3-dione.

The structure of the title compound, C20H29NO2, is isotypic to that of its homologue 1-octylindoline-2,3-dione. The indoline ring and the two carbonyl-group O atoms are approximately coplanar, the largest deviation from the mean plane being 0.0760 (10) Å. The mean plane through the fused-ring system is nearly perpendicular to the mean plane passing through the 1-dodecyl chain [dihedral angle = 77.69 (5)°]. All C atoms of the dodecyl group are in an anti-periplanar arrangement. In the crystal, mol-ecules are linked by C-H⋯O hydrogen bonds, forming a three-dimensional network.

Related literature

For 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 similar compounds see: Qachchachi et al. (2013 ▶).

Experimental

Crystal data

C20H29NO2

M = 315.44

Monoclinic,

a = 25.2013 (7) Å

b = 4.66818 (9) Å

c = 15.7013 (4) Å

β = 104.926 (3)°

V = 1784.84 (7) Å3

Z = 4

Cu Kα radiation

μ = 0.58 mm−1

T = 123 K

0.12 × 0.11 × 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 = 0.942, T max = 0.979

12640 measured reflections

3493 independent reflections

3039 reflections with I > 2σ(I)

R int = 0.021

Refinement

R[F 2 > 2σ(F 2)] = 0.035

wR(F 2) = 0.100

S = 1.02

3493 reflections

208 parameters

H-atom parameters constrained

Δρmax = 0.29 e Å−3

Δρmin = −0.20 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: ORTEP-3 for Windows (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/S1600536814001792/rz5103sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814001792/rz5103Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814001792/rz5103Isup3.cml

CCDC reference:

Additional supporting information: crystallographic information; 3D view; checkCIF report

C20H29NO2	F(000) = 688
Mr = 315.44	Dx = 1.174 Mg m−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.54184 Å
Hall symbol: -P 2ybc	Cell parameters from 6237 reflections
a = 25.2013 (7) Å	θ = 5.4–73.8°
b = 4.66818 (9) Å	µ = 0.58 mm−1
c = 15.7013 (4) Å	T = 123 K
β = 104.926 (3)°	Plate, clear light orange
V = 1784.84 (7) Å3	0.12 × 0.11 × 0.04 mm
Z = 4

Oxford Diffraction SuperNova (single source at offset, Atlas) diffractometer	3493 independent reflections
Radiation source: SuperNova (Cu) X-ray Source	3039 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.021
Detector resolution: 10.3546 pixels mm-1	θmax = 73.6°, θmin = 3.6°
ω scans	h = −31→30
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 = 0.942, Tmax = 0.979	l = −19→18
12640 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)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.100	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.0528P)2 + 0.4135P] where P = (Fo2 + 2Fc2)/3
3493 reflections	(Δ/σ)max = 0.001
208 parameters	Δρmax = 0.29 e Å−3
0 restraints	Δρmin = −0.20 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
C1	0.11717 (4)	0.3582 (2)	0.56405 (7)	0.0263 (2)
C2	0.07145 (4)	0.5831 (2)	0.52742 (7)	0.0256 (2)
C3	0.07308 (4)	0.6313 (2)	0.43624 (7)	0.0221 (2)
C4	0.11376 (4)	0.4511 (2)	0.41950 (7)	0.0207 (2)
C5	0.12551 (4)	0.4485 (2)	0.33845 (7)	0.0243 (2)
H5	0.1527	0.3249	0.3268	0.029*
C6	0.09572 (4)	0.6350 (2)	0.27432 (7)	0.0264 (2)
H6	0.1030	0.6382	0.2179	0.032*
C7	0.05561 (4)	0.8162 (2)	0.29048 (7)	0.0280 (2)
H7	0.0363	0.9419	0.2455	0.034*
C8	0.04351 (4)	0.8149 (2)	0.37185 (7)	0.0258 (2)
H8	0.0158	0.9361	0.3831	0.031*
C9	0.18532 (4)	0.0978 (2)	0.50360 (8)	0.0262 (2)
H9A	0.1802	−0.0161	0.4489	0.031*
H9B	0.1870	−0.0370	0.5529	0.031*
C10	0.23949 (4)	0.2615 (2)	0.52023 (8)	0.0264 (2)
H10A	0.2396	0.3770	0.4674	0.032*
H10B	0.2421	0.3951	0.5701	0.032*
C11	0.28944 (4)	0.0655 (2)	0.54105 (8)	0.0261 (2)
H11A	0.2866	−0.0697	0.4915	0.031*
H11B	0.2896	−0.0483	0.5943	0.031*
C12	0.34340 (4)	0.2303 (2)	0.55654 (8)	0.0269 (2)
H12A	0.3441	0.3339	0.5018	0.032*
H12B	0.3448	0.3748	0.6032	0.032*
C13	0.39431 (4)	0.0414 (3)	0.58348 (8)	0.0275 (2)
H13A	0.3930	−0.1032	0.5369	0.033*
H13B	0.3938	−0.0620	0.6383	0.033*
C14	0.44783 (4)	0.2094 (3)	0.59858 (8)	0.0283 (3)
H14A	0.4485	0.3105	0.5434	0.034*
H14B	0.4487	0.3563	0.6444	0.034*
C15	0.49914 (4)	0.0237 (3)	0.62696 (8)	0.0285 (3)
H15A	0.4984	−0.1232	0.5812	0.034*
H15B	0.4986	−0.0771	0.6822	0.034*
C16	0.55241 (4)	0.1948 (3)	0.64174 (8)	0.0290 (3)
H16A	0.5528	0.2957	0.5865	0.035*
H16B	0.5531	0.3416	0.6875	0.035*
C17	0.60399 (4)	0.0110 (3)	0.67010 (8)	0.0290 (3)
H17A	0.6033	−0.1358	0.6243	0.035*
H17B	0.6036	−0.0900	0.7254	0.035*
C18	0.65705 (4)	0.1830 (3)	0.68478 (8)	0.0287 (3)
H18A	0.6574	0.2838	0.6294	0.034*
H18B	0.6576	0.3302	0.7304	0.034*
C19	0.70879 (4)	0.0017 (3)	0.71327 (8)	0.0319 (3)
H19A	0.7083	−0.1461	0.6678	0.038*
H19B	0.7087	−0.0981	0.7689	0.038*
C20	0.76140 (5)	0.1765 (3)	0.72716 (9)	0.0383 (3)
H20A	0.7626	0.3204	0.7731	0.046*
H20B	0.7622	0.2724	0.6720	0.046*
H20C	0.7932	0.0491	0.7453	0.046*
N1	0.13859 (4)	0.2877 (2)	0.49531 (6)	0.0237 (2)
O1	0.13183 (4)	0.2676 (2)	0.63893 (5)	0.0368 (2)
O2	0.04303 (3)	0.6876 (2)	0.57083 (5)	0.0350 (2)

	U11	U22	U33	U12	U13	U23
C1	0.0228 (5)	0.0325 (6)	0.0234 (5)	−0.0083 (4)	0.0058 (4)	−0.0017 (5)
C2	0.0203 (5)	0.0317 (6)	0.0250 (5)	−0.0069 (4)	0.0063 (4)	−0.0076 (5)
C3	0.0169 (4)	0.0255 (5)	0.0240 (5)	−0.0034 (4)	0.0056 (4)	−0.0056 (4)
C4	0.0168 (4)	0.0231 (5)	0.0212 (5)	−0.0028 (4)	0.0029 (4)	−0.0021 (4)
C5	0.0201 (5)	0.0290 (5)	0.0248 (5)	0.0006 (4)	0.0077 (4)	−0.0035 (4)
C6	0.0262 (5)	0.0324 (6)	0.0206 (5)	−0.0028 (5)	0.0063 (4)	−0.0013 (4)
C7	0.0248 (5)	0.0290 (6)	0.0274 (6)	0.0008 (4)	0.0017 (4)	0.0018 (5)
C8	0.0192 (5)	0.0263 (5)	0.0308 (6)	0.0010 (4)	0.0044 (4)	−0.0040 (5)
C9	0.0192 (5)	0.0256 (5)	0.0320 (6)	0.0005 (4)	0.0034 (4)	0.0025 (5)
C10	0.0192 (5)	0.0257 (5)	0.0322 (6)	−0.0005 (4)	0.0031 (4)	0.0015 (5)
C11	0.0188 (5)	0.0277 (5)	0.0297 (6)	0.0002 (4)	0.0025 (4)	0.0019 (5)
C12	0.0193 (5)	0.0294 (6)	0.0308 (6)	−0.0003 (4)	0.0042 (4)	0.0016 (5)
C13	0.0188 (5)	0.0316 (6)	0.0308 (6)	0.0004 (4)	0.0038 (4)	0.0014 (5)
C14	0.0189 (5)	0.0336 (6)	0.0315 (6)	0.0002 (4)	0.0046 (4)	0.0015 (5)
C15	0.0188 (5)	0.0342 (6)	0.0315 (6)	0.0005 (4)	0.0043 (4)	0.0023 (5)
C16	0.0191 (5)	0.0345 (6)	0.0323 (6)	0.0000 (4)	0.0048 (4)	0.0004 (5)
C17	0.0194 (5)	0.0357 (6)	0.0308 (6)	0.0012 (5)	0.0047 (4)	0.0034 (5)
C18	0.0194 (5)	0.0355 (6)	0.0300 (6)	0.0003 (4)	0.0041 (4)	0.0005 (5)
C19	0.0217 (5)	0.0403 (6)	0.0326 (6)	0.0029 (5)	0.0052 (5)	0.0050 (5)
C20	0.0193 (5)	0.0507 (8)	0.0428 (7)	0.0010 (5)	0.0044 (5)	0.0007 (6)
N1	0.0187 (4)	0.0286 (5)	0.0232 (5)	−0.0001 (4)	0.0042 (3)	0.0013 (4)
O1	0.0369 (5)	0.0487 (5)	0.0239 (4)	−0.0068 (4)	0.0060 (3)	0.0062 (4)
O2	0.0287 (4)	0.0505 (5)	0.0288 (4)	−0.0021 (4)	0.0127 (3)	−0.0127 (4)

C1—O1	1.2142 (14)	C12—H12A	0.9900
C1—N1	1.3656 (14)	C12—H12B	0.9900
C1—C2	1.5552 (16)	C13—C14	1.5252 (14)
C2—O2	1.2113 (13)	C13—H13A	0.9900
C2—C3	1.4601 (14)	C13—H13B	0.9900
C3—C8	1.3869 (16)	C14—C15	1.5251 (15)
C3—C4	1.4027 (14)	C14—H14A	0.9900
C4—C5	1.3789 (14)	C14—H14B	0.9900
C4—N1	1.4163 (14)	C15—C16	1.5275 (14)
C5—C6	1.3950 (16)	C15—H15A	0.9900
C5—H5	0.9500	C15—H15B	0.9900
C6—C7	1.3909 (16)	C16—C17	1.5250 (15)
C6—H6	0.9500	C16—H16A	0.9900
C7—C8	1.3878 (15)	C16—H16B	0.9900
C7—H7	0.9500	C17—C18	1.5257 (15)
C8—H8	0.9500	C17—H17A	0.9900
C9—N1	1.4528 (13)	C17—H17B	0.9900
C9—C10	1.5270 (14)	C18—C19	1.5220 (15)
C9—H9A	0.9900	C18—H18A	0.9900
C9—H9B	0.9900	C18—H18B	0.9900
C10—C11	1.5222 (14)	C19—C20	1.5239 (16)
C10—H10A	0.9900	C19—H19A	0.9900
C10—H10B	0.9900	C19—H19B	0.9900
C11—C12	1.5265 (14)	C20—H20A	0.9800
C11—H11A	0.9900	C20—H20B	0.9800
C11—H11B	0.9900	C20—H20C	0.9800
C12—C13	1.5238 (14)
O1—C1—N1	126.70 (11)	C14—C13—H13A	108.9
O1—C1—C2	127.24 (10)	C12—C13—H13B	108.9
N1—C1—C2	106.04 (9)	C14—C13—H13B	108.9
O2—C2—C3	131.26 (11)	H13A—C13—H13B	107.8
O2—C2—C1	123.57 (10)	C15—C14—C13	113.73 (10)
C3—C2—C1	105.16 (8)	C15—C14—H14A	108.8
C8—C3—C4	121.03 (10)	C13—C14—H14A	108.8
C8—C3—C2	131.64 (10)	C15—C14—H14B	108.8
C4—C3—C2	107.32 (9)	C13—C14—H14B	108.8
C5—C4—C3	121.28 (10)	H14A—C14—H14B	107.7
C5—C4—N1	128.13 (9)	C14—C15—C16	113.14 (10)
C3—C4—N1	110.58 (9)	C14—C15—H15A	109.0
C4—C5—C6	117.21 (9)	C16—C15—H15A	109.0
C4—C5—H5	121.4	C14—C15—H15B	109.0
C6—C5—H5	121.4	C16—C15—H15B	109.0
C7—C6—C5	121.95 (10)	H15A—C15—H15B	107.8
C7—C6—H6	119.0	C17—C16—C15	113.57 (10)
C5—C6—H6	119.0	C17—C16—H16A	108.9
C8—C7—C6	120.51 (10)	C15—C16—H16A	108.9
C8—C7—H7	119.7	C17—C16—H16B	108.9
C6—C7—H7	119.7	C15—C16—H16B	108.9
C3—C8—C7	118.01 (10)	H16A—C16—H16B	107.7
C3—C8—H8	121.0	C16—C17—C18	113.33 (10)
C7—C8—H8	121.0	C16—C17—H17A	108.9
N1—C9—C10	112.22 (9)	C18—C17—H17A	108.9
N1—C9—H9A	109.2	C16—C17—H17B	108.9
C10—C9—H9A	109.2	C18—C17—H17B	108.9
N1—C9—H9B	109.2	H17A—C17—H17B	107.7
C10—C9—H9B	109.2	C19—C18—C17	113.75 (10)
H9A—C9—H9B	107.9	C19—C18—H18A	108.8
C11—C10—C9	112.92 (9)	C17—C18—H18A	108.8
C11—C10—H10A	109.0	C19—C18—H18B	108.8
C9—C10—H10A	109.0	C17—C18—H18B	108.8
C11—C10—H10B	109.0	H18A—C18—H18B	107.7
C9—C10—H10B	109.0	C18—C19—C20	113.08 (11)
H10A—C10—H10B	107.8	C18—C19—H19A	109.0
C10—C11—C12	112.63 (9)	C20—C19—H19A	109.0
C10—C11—H11A	109.1	C18—C19—H19B	109.0
C12—C11—H11A	109.1	C20—C19—H19B	109.0
C10—C11—H11B	109.1	H19A—C19—H19B	107.8
C12—C11—H11B	109.1	C19—C20—H20A	109.5
H11A—C11—H11B	107.8	C19—C20—H20B	109.5
C13—C12—C11	113.86 (9)	H20A—C20—H20B	109.5
C13—C12—H12A	108.8	C19—C20—H20C	109.5
C11—C12—H12A	108.8	H20A—C20—H20C	109.5
C13—C12—H12B	108.8	H20B—C20—H20C	109.5
C11—C12—H12B	108.8	C1—N1—C4	110.82 (9)
H12A—C12—H12B	107.7	C1—N1—C9	123.54 (9)
C12—C13—C14	113.16 (9)	C4—N1—C9	125.19 (9)
C12—C13—H13A	108.9

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···O1i	0.95	2.47	3.1423 (14)	127
C6—H6···O2ii	0.95	2.55	3.2360 (13)	130
C8—H8···O2iii	0.95	2.52	3.4598 (13)	169

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6⋯O1i	0.95	2.47	3.1423 (14)	127
C6—H6⋯O2ii	0.95	2.55	3.2360 (13)	130
C8—H8⋯O2iii	0.95	2.52	3.4598 (13)	169

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