1-Decyl­indoline-2,3-dione

Mamari, K.; Zouihri, H.; Essassi, E.M.; Ng, S.W.

doi:10.1107/S1600536810018271

organic compounds

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ISSN: 2056-9890

Volume 66| Part 6| June 2010| Page o1411

https://doi.org/10.1107/S1600536810018271

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1-Decylindoline-2,3-dione

Khalil Mamari,^a Hafid Zouihri,^b El Mokhtar Essassi ^a and Seik Weng Ng ^c ^*

^aLaboratoire de Chimie Organique Hétérocyclique, Pôle de Compétences Pharmacochimie, Université Mohammed V-Agdal, BP 1014 Avenue Ibn Batout, Rabat, Morocco, ^bCNRST Division UATRS, Angle Allal Fassi/FAR, BP 8027 Hay Riad, Rabat, Morocco, and ^cDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: seikweng@um.edu.my

(Received 15 May 2010; accepted 17 May 2010; online 22 May 2010)

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, P 2₁ /c
a = 22.7208 (3) Å
b = 4.7189 (1) Å
c = 15.8254 (1) Å
β = 106.827 (1)°
V = 1624.10 (4) Å³
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[F² > 2σ(F²)] = 0.046
wR(F²) = 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 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536810018271/bt5274sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810018271/bt5274Isup2.hkl

checkCIF report

Comment top

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).

Related literature top

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 top

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.

Structure description top

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).

Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); 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).

Figures top

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.

1-Decylindoline-2,3-dione top

Crystal data top

C₁₈H₂₅NO₂	F(000) = 624
M_r = 287.39	D_x = 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 top

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

Refinement top

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 = 1.03	w = 1/[σ²(F_o²) + (0.0928P)² + 0.1263P] where P = (F_o² + 2F_c²)/3
5240 reflections	(Δ/σ)_max = 0.001
190 parameters	Δρ_max = 0.29 e Å⁻³
0 restraints	Δρ_min = −0.20 e Å⁻³

Crystal data top

C₁₈H₂₅NO₂	V = 1624.10 (4) Å³
M_r = 287.39	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 22.7208 (3) Å	µ = 0.08 mm⁻¹
b = 4.7189 (1) Å	T = 200 K
c = 15.8254 (1) Å	0.27 × 0.18 × 0.15 mm
β = 106.827 (1)°

Data collection top

Bruker X8 APEXII diffractometer	3869 reflections with I > 2σ(I)
24714 measured reflections	R_int = 0.028
5240 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.046	0 restraints
wR(F²) = 0.154	H-atom parameters constrained
S = 1.03	Δρ_max = 0.29 e Å⁻³
5240 reflections	Δρ_min = −0.20 e Å⁻³
190 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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 (Å²) top

	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, º) top

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)

Experimental details

Crystal data
Chemical formula	C₁₈H₂₅NO₂
M_r	287.39
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	200
a, b, c (Å)	22.7208 (3), 4.7189 (1), 15.8254 (1)
β (°)	106.827 (1)
V (Å³)	1624.10 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.27 × 0.18 × 0.15

Data collection
Diffractometer	Bruker X8 APEXII
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	24714, 5240, 3869
R_int	0.028
(sin θ/λ)_max (Å⁻¹)	0.729

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.046, 0.154, 1.03
No. of reflections	5240
No. of parameters	190
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.29, −0.20

Computer programs: APEX2 (Bruker, 2008), SAINT (Bruker, 2008), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2010).

Acknowledgements

We thank Université Mohammed V-Agdal and the University of Malaya for supporting this study.

References

Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191. CrossRef CAS Google Scholar
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