1-Decyl­indoline-2,3-dione

Abstract

In the title N-alkyl isatin, C₁₈H₂₅NO₂, the isatin moiety is almost planar (r.m.s. deviation = 0.03 Å). C—C—C—C torsion angles of the decyl substituent indicate an all-antiperiplanar conformation.

Related literature

For background to N-substituted isatins and their derivatives, see: Bouhfid et al. (2008 ▶). For the crystal structures of two N-alkyl isatins, see: see: Miehe et al. (2003 ▶); Naumov et al. (2002 ▶).

Experimental

Crystal data

• C₁₈H₂₅NO₂

• M _r = 287.39

• Monoclinic,

• a = 22.7208 (3) Å

• b = 4.7189 (1) Å

• c = 15.8254 (1) Å

• β = 106.827 (1)°

• V = 1624.10 (4) ų

• Z = 4

• Mo Kα radiation

• μ = 0.08 mm⁻¹

• T = 200 K

• 0.27 × 0.18 × 0.15 mm

Data collection

• Bruker X8 APEXII diffractometer

• 24714 measured reflections

• 5240 independent reflections

• 3869 reflections with I > 2σ(I)

• R _int = 0.028

Refinement

• R[F ² > 2σ(F ²)] = 0.046

• wR(F ²) = 0.154

• S = 1.03

• 5240 reflections

• 190 parameters

• H-atom parameters constrained

• Δρ_max = 0.29 e Å⁻³

• Δρ_min = −0.20 e Å⁻³

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT (Bruker, 2008 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: X-SEED (Barbour, 2001 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Supplementary Material

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

supplementary crystallographic information

Comment

N-Substituted isatins (Bouhfid et al., 2008) represent a large family of heterocyclic compounds reported to show a wide range of useful medicinal activities. These are readily synthesized by the reaction of isatin and an alkyl halide in the presence of a catalyst. The title decyl derivative (Scheme I, Fig. 1) has a particarly long hydrocarbon chain; the chain adopts a extended zigzag conformation.

The crystal structures of only few N-substituted isatins have been reported; these have only short hydrocarbon chains, e.g., methyl isatin (Miehe et al., 2003) and ethyl isatin (Naumov et al., 2002).

Experimental

To a solution of isatin (1 g, 6.8 mmol) dissolved in DMF(50 ml) was added 1-bromodecane (1.50 g, 6.8 mmol), potassium carbonate (1 g, 7.4 mmol) and a catalytic quantity of tetra-n-butylammonium bromide.The mixture was stirred for 48 h; the reaction was monitored by thin layer chromatography. The mixture was filtered and the solvent removed under vacuum. The solid that was obtained was recrystallized from ethanol to afford the title compound as orange crystals in 80% yield.

Refinement

H-atoms were placed in calculated positions (C–H 0.95–0.99 Å) and were included in the refinement in the riding model approximation, with U(H) set to 1.2–1.5U_eq(C).

Figures

Fig. 1.

Anisotropic displacement ellipsoid plot (Barbour, 2001) of the title compound at the 70% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.

Crystal data

C18H25NO2	F(000) = 624
Mr = 287.39	Dx = 1.175 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 7695 reflections
a = 22.7208 (3) Å	θ = 2.6–30.8°
b = 4.7189 (1) Å	µ = 0.08 mm−1
c = 15.8254 (1) Å	T = 200 K
β = 106.827 (1)°	Prism, orange
V = 1624.10 (4) Å3	0.27 × 0.18 × 0.15 mm
Z = 4

Data collection

Bruker X8 APEXII diffractometer	3869 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.028
graphite	θmax = 31.2°, θmin = 2.7°
φ and ω scans	h = −31→33
24714 measured reflections	k = −6→6
5240 independent reflections	l = −23→23

Refinement

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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.154	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.0928P)2 + 0.1263P] where P = (Fo2 + 2Fc2)/3
5240 reflections	(Δ/σ)max = 0.001
190 parameters	Δρmax = 0.29 e Å−3
0 restraints	Δρmin = −0.20 e Å−3

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
O1	0.45133 (4)	1.1915 (2)	0.42722 (6)	0.0500 (2)
O2	0.35296 (4)	0.7723 (2)	0.35480 (5)	0.0532 (3)
N1	0.34580 (4)	0.78714 (18)	0.49718 (5)	0.03110 (19)
C1	0.37349 (4)	0.94803 (19)	0.57377 (6)	0.02594 (19)
C2	0.36083 (4)	0.9424 (2)	0.65378 (6)	0.0307 (2)
H2	0.3307	0.8180	0.6640	0.037*
C3	0.39391 (5)	1.1265 (2)	0.71908 (7)	0.0344 (2)
H3	0.3859	1.1275	0.7748	0.041*
C4	0.43815 (5)	1.3082 (2)	0.70538 (7)	0.0361 (2)
H4	0.4596	1.4322	0.7512	0.043*
C5	0.45126 (4)	1.3101 (2)	0.62509 (7)	0.0334 (2)
H5	0.4820	1.4320	0.6155	0.040*
C6	0.41840 (4)	1.1295 (2)	0.55931 (6)	0.0276 (2)
C7	0.42008 (4)	1.0850 (2)	0.46877 (6)	0.0337 (2)
C8	0.36942 (5)	0.8606 (2)	0.42990 (7)	0.0353 (2)
C9	0.29367 (4)	0.5981 (2)	0.48624 (8)	0.0352 (2)
H9A	0.2996	0.4841	0.5406	0.042*
H9B	0.2918	0.4661	0.4369	0.042*
C10	0.23300 (4)	0.7587 (2)	0.46748 (8)	0.0358 (2)
H10A	0.2329	0.8711	0.5202	0.043*
H10B	0.2299	0.8926	0.4182	0.043*
C11	0.17722 (5)	0.5653 (2)	0.44377 (8)	0.0357 (2)
H11A	0.1806	0.4294	0.4926	0.043*
H11B	0.1769	0.4551	0.3904	0.043*
C12	0.11684 (4)	0.7268 (2)	0.42654 (8)	0.0368 (2)
H12A	0.1163	0.8268	0.4813	0.044*
H12B	0.1151	0.8720	0.3807	0.044*
C13	0.05984 (4)	0.5417 (2)	0.39672 (8)	0.0375 (2)
H13A	0.0614	0.3963	0.4424	0.045*
H13B	0.0601	0.4421	0.3418	0.045*
C14	0.00008 (4)	0.7073 (2)	0.38011 (8)	0.0385 (2)
H14A	−0.0003	0.8047	0.4353	0.046*
H14B	−0.0011	0.8547	0.3352	0.046*
C15	−0.05752 (5)	0.5260 (3)	0.34891 (8)	0.0387 (2)
H15A	−0.0573	0.4288	0.2936	0.046*
H15B	−0.0565	0.3784	0.3938	0.046*
C16	−0.11691 (5)	0.6935 (3)	0.33263 (8)	0.0395 (3)
H16A	−0.1171	0.7898	0.3881	0.047*
H16B	−0.1177	0.8418	0.2881	0.047*
C17	−0.17475 (5)	0.5154 (3)	0.30097 (8)	0.0447 (3)
H17A	−0.1748	0.4204	0.2452	0.054*
H17B	−0.1739	0.3662	0.3453	0.054*
C18	−0.23353 (5)	0.6849 (3)	0.28575 (10)	0.0566 (4)
H18A	−0.2690	0.5581	0.2657	0.085*
H18B	−0.2353	0.8299	0.2407	0.085*
H18C	−0.2343	0.7764	0.3410	0.085*

Atomic displacement parameters (Ų)

	U11	U22	U33	U12	U13	U23
O1	0.0417 (5)	0.0751 (6)	0.0390 (4)	0.0036 (4)	0.0209 (4)	0.0194 (4)
O2	0.0543 (5)	0.0716 (6)	0.0319 (4)	0.0113 (5)	0.0098 (4)	−0.0109 (4)
N1	0.0264 (4)	0.0362 (4)	0.0297 (4)	0.0000 (3)	0.0065 (3)	−0.0030 (3)
C1	0.0214 (4)	0.0288 (4)	0.0270 (4)	0.0035 (3)	0.0061 (3)	0.0038 (3)
C2	0.0274 (4)	0.0361 (5)	0.0309 (5)	−0.0008 (4)	0.0122 (4)	0.0047 (4)
C3	0.0352 (5)	0.0422 (5)	0.0269 (5)	0.0028 (4)	0.0106 (4)	0.0015 (4)
C4	0.0332 (5)	0.0385 (5)	0.0337 (5)	−0.0015 (4)	0.0050 (4)	−0.0031 (4)
C5	0.0262 (4)	0.0347 (5)	0.0378 (5)	−0.0025 (4)	0.0072 (4)	0.0055 (4)
C6	0.0220 (4)	0.0328 (5)	0.0290 (4)	0.0038 (3)	0.0089 (3)	0.0071 (3)
C7	0.0277 (4)	0.0452 (6)	0.0298 (5)	0.0099 (4)	0.0107 (4)	0.0108 (4)
C8	0.0312 (5)	0.0453 (6)	0.0291 (5)	0.0121 (4)	0.0085 (4)	0.0007 (4)
C9	0.0259 (4)	0.0311 (5)	0.0447 (6)	0.0003 (4)	0.0040 (4)	−0.0051 (4)
C10	0.0260 (5)	0.0313 (5)	0.0464 (6)	0.0014 (4)	0.0045 (4)	−0.0027 (4)
C11	0.0260 (4)	0.0335 (5)	0.0442 (6)	0.0002 (4)	0.0047 (4)	−0.0039 (4)
C12	0.0260 (5)	0.0362 (5)	0.0454 (6)	0.0002 (4)	0.0057 (4)	−0.0029 (4)
C13	0.0257 (5)	0.0385 (5)	0.0457 (6)	−0.0002 (4)	0.0064 (4)	−0.0040 (4)
C14	0.0253 (5)	0.0405 (6)	0.0471 (6)	0.0003 (4)	0.0064 (4)	−0.0017 (5)
C15	0.0264 (5)	0.0429 (6)	0.0447 (6)	−0.0003 (4)	0.0068 (4)	−0.0052 (5)
C16	0.0264 (5)	0.0451 (6)	0.0451 (6)	0.0005 (4)	0.0072 (4)	−0.0012 (5)
C17	0.0295 (5)	0.0528 (7)	0.0494 (7)	−0.0040 (5)	0.0076 (5)	−0.0083 (5)
C18	0.0265 (5)	0.0727 (9)	0.0673 (9)	−0.0007 (6)	0.0081 (5)	−0.0007 (7)

Geometric parameters (Å, °)

O1—C7	1.2080 (12)	C11—H11A	0.9900
O2—C8	1.2118 (13)	C11—H11B	0.9900
N1—C8	1.3684 (13)	C12—C13	1.5196 (15)
N1—C1	1.4142 (12)	C12—H12A	0.9900
N1—C9	1.4525 (13)	C12—H12B	0.9900
C1—C2	1.3774 (13)	C13—C14	1.5222 (14)
C1—C6	1.4007 (13)	C13—H13A	0.9900
C2—C3	1.3919 (15)	C13—H13B	0.9900
C2—H2	0.9500	C14—C15	1.5213 (14)
C3—C4	1.3852 (15)	C14—H14A	0.9900
C3—H3	0.9500	C14—H14B	0.9900
C4—C5	1.3865 (15)	C15—C16	1.5201 (15)
C4—H4	0.9500	C15—H15A	0.9900
C5—C6	1.3846 (14)	C15—H15B	0.9900
C5—H5	0.9500	C16—C17	1.5173 (15)
C6—C7	1.4596 (13)	C16—H16A	0.9900
C7—C8	1.5540 (17)	C16—H16B	0.9900
C9—C10	1.5248 (14)	C17—C18	1.5151 (17)
C9—H9A	0.9900	C17—H17A	0.9900
C9—H9B	0.9900	C17—H17B	0.9900
C10—C11	1.5181 (14)	C18—H18A	0.9800
C10—H10A	0.9900	C18—H18B	0.9800
C10—H10B	0.9900	C18—H18C	0.9800
C11—C12	1.5233 (14)
C8—N1—C1	110.70 (8)	H11A—C11—H11B	107.8
C8—N1—C9	123.56 (9)	C13—C12—C11	114.23 (9)
C1—N1—C9	125.23 (8)	C13—C12—H12A	108.7
C2—C1—C6	121.18 (9)	C11—C12—H12A	108.7
C2—C1—N1	128.18 (9)	C13—C12—H12B	108.7
C6—C1—N1	110.65 (8)	C11—C12—H12B	108.7
C1—C2—C3	117.32 (9)	H12A—C12—H12B	107.6
C1—C2—H2	121.3	C12—C13—C14	113.32 (9)
C3—C2—H2	121.3	C12—C13—H13A	108.9
C4—C3—C2	122.03 (9)	C14—C13—H13A	108.9
C4—C3—H3	119.0	C12—C13—H13B	108.9
C2—C3—H3	119.0	C14—C13—H13B	108.9
C3—C4—C5	120.36 (10)	H13A—C13—H13B	107.7
C3—C4—H4	119.8	C15—C14—C13	114.06 (9)
C5—C4—H4	119.8	C15—C14—H14A	108.7
C6—C5—C4	118.22 (9)	C13—C14—H14A	108.7
C6—C5—H5	120.9	C15—C14—H14B	108.7
C4—C5—H5	120.9	C13—C14—H14B	108.7
C5—C6—C1	120.88 (9)	H14A—C14—H14B	107.6
C5—C6—C7	131.68 (9)	C16—C15—C14	113.61 (9)
C1—C6—C7	107.44 (9)	C16—C15—H15A	108.8
O1—C7—C6	131.37 (11)	C14—C15—H15A	108.8
O1—C7—C8	123.56 (10)	C16—C15—H15B	108.8
C6—C7—C8	105.05 (8)	C14—C15—H15B	108.8
O2—C8—N1	126.65 (11)	H15A—C15—H15B	107.7
O2—C8—C7	127.25 (10)	C17—C16—C15	114.17 (10)
N1—C8—C7	106.08 (8)	C17—C16—H16A	108.7
N1—C9—C10	112.21 (8)	C15—C16—H16A	108.7
N1—C9—H9A	109.2	C17—C16—H16B	108.7
C10—C9—H9A	109.2	C15—C16—H16B	108.7
N1—C9—H9B	109.2	H16A—C16—H16B	107.6
C10—C9—H9B	109.2	C18—C17—C16	113.55 (11)
H9A—C9—H9B	107.9	C18—C17—H17A	108.9
C11—C10—C9	113.10 (8)	C16—C17—H17A	108.9
C11—C10—H10A	109.0	C18—C17—H17B	108.9
C9—C10—H10A	109.0	C16—C17—H17B	108.9
C11—C10—H10B	109.0	H17A—C17—H17B	107.7
C9—C10—H10B	109.0	C17—C18—H18A	109.5
H10A—C10—H10B	107.8	C17—C18—H18B	109.5
C10—C11—C12	112.81 (8)	H18A—C18—H18B	109.5
C10—C11—H11A	109.0	C17—C18—H18C	109.5
C12—C11—H11A	109.0	H18A—C18—H18C	109.5
C10—C11—H11B	109.0	H18B—C18—H18C	109.5
C12—C11—H11B	109.0
C8—N1—C1—C2	177.81 (9)	C1—N1—C8—O2	−175.80 (10)
C9—N1—C1—C2	5.74 (15)	C9—N1—C8—O2	−3.58 (17)
C8—N1—C1—C6	−1.83 (11)	C1—N1—C8—C7	2.68 (10)
C9—N1—C1—C6	−173.90 (9)	C9—N1—C8—C7	174.90 (8)
C6—C1—C2—C3	0.75 (14)	O1—C7—C8—O2	−3.09 (17)
N1—C1—C2—C3	−178.85 (9)	C6—C7—C8—O2	175.90 (10)
C1—C2—C3—C4	−0.33 (15)	O1—C7—C8—N1	178.44 (10)
C2—C3—C4—C5	−0.54 (16)	C6—C7—C8—N1	−2.57 (10)
C3—C4—C5—C6	0.97 (15)	C8—N1—C9—C10	−93.70 (12)
C4—C5—C6—C1	−0.55 (14)	C1—N1—C9—C10	77.39 (12)
C4—C5—C6—C7	178.57 (10)	N1—C9—C10—C11	172.33 (9)
C2—C1—C6—C5	−0.32 (14)	C9—C10—C11—C12	179.09 (9)
N1—C1—C6—C5	179.35 (8)	C10—C11—C12—C13	176.17 (10)
C2—C1—C6—C7	−179.63 (8)	C11—C12—C13—C14	179.87 (9)
N1—C1—C6—C7	0.04 (10)	C12—C13—C14—C15	179.16 (10)
C5—C6—C7—O1	1.18 (19)	C13—C14—C15—C16	179.93 (10)
C1—C6—C7—O1	−179.61 (11)	C14—C15—C16—C17	179.67 (10)
C5—C6—C7—C8	−177.70 (10)	C15—C16—C17—C18	179.53 (11)
C1—C6—C7—C8	1.50 (10)