1-Decyl-indoline-2,3-dione.

In the title N-alkyl isatin, C(18)H(25)NO(2), 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 = 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) 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[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.154

S = 1.03

5240 reflections

190 parameters

H-atom parameters constrained

Δρmax = 0.29 e Å−3

Δρmin = −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 ▶).

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

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810018271/bt5274Isup2.hkl

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

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

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 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

	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*

	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)

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)