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

In the title N-alkyl isatin, C(22)H(33)NO(2), the isatin moiety is planar (r.m.s. deviation = 0.03 Å). The tetra-decyl substituent has all torsion angles in an anti-periplanar 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: Miehe et al. (2003 ▶); Naumov et al. (2002 ▶).

Experimental

Crystal data

C22H33NO2

M = 343.49

Monoclinic,

a = 27.6647 (8) Å

b = 4.7055 (1) Å

c = 15.7583 (5) Å

β = 103.635 (1)°

V = 1993.54 (10) Å3

Z = 4

Mo Kα radiation

μ = 0.07 mm−1

T = 200 K

0.18 × 0.16 × 0.11 mm

Data collection

Bruker X8 APEXII diffractometer

23477 measured reflections

5172 independent reflections

3532 reflections with I > 2σ(I)

R int = 0.042

Refinement

R[F 2 > 2σ(F 2)] = 0.065

wR(F 2) = 0.222

S = 1.11

5172 reflections

226 parameters

H-atom parameters constrained

Δρmax = 0.27 e Å−3

Δρmin = −0.21 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/S1600536810018258/bt5273sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810018258/bt5273Isup2.hkl

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

C22H33NO2	F(000) = 752
Mr = 343.49	Dx = 1.144 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4926 reflections
a = 27.6647 (8) Å	θ = 2.6–28.7°
b = 4.7055 (1) Å	µ = 0.07 mm−1
c = 15.7583 (5) Å	T = 200 K
β = 103.635 (1)°	Irregular block, orange
V = 1993.54 (10) Å3	0.18 × 0.16 × 0.11 mm
Z = 4

Bruker X8 APEXII diffractometer	3532 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.042
graphite	θmax = 28.8°, θmin = 2.3°
φ and ω scans	h = −37→37
23477 measured reflections	k = −6→5
5172 independent reflections	l = −21→21

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)] = 0.065	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.222	H-atom parameters constrained
S = 1.11	w = 1/[σ2(Fo2) + (0.098P)2 + 1.1616P] where P = (Fo2 + 2Fc2)/3
5172 reflections	(Δ/σ)max = 0.001
226 parameters	Δρmax = 0.27 e Å−3
0 restraints	Δρmin = −0.20 e Å−3

	x	y	z	Uiso*/Ueq
O1	0.46046 (6)	1.1884 (4)	0.43051 (11)	0.0487 (5)
O2	0.38053 (7)	0.7712 (5)	0.36601 (11)	0.0524 (5)
N1	0.37452 (6)	0.7894 (4)	0.50944 (11)	0.0309 (4)
C1	0.39707 (7)	0.9506 (4)	0.58407 (12)	0.0263 (4)
C2	0.38674 (7)	0.9454 (5)	0.66525 (13)	0.0312 (4)
H2	0.3623	0.8214	0.6780	0.037*
C3	0.41379 (8)	1.1306 (5)	0.72815 (14)	0.0352 (5)
H3	0.4073	1.1327	0.7847	0.042*
C4	0.44969 (8)	1.3112 (5)	0.71059 (15)	0.0376 (5)
H4	0.4672	1.4355	0.7548	0.045*
C5	0.46031 (7)	1.3115 (5)	0.62847 (14)	0.0339 (5)
H5	0.4852	1.4326	0.6160	0.041*
C6	0.43356 (7)	1.1305 (4)	0.56570 (12)	0.0282 (4)
C7	0.43501 (7)	1.0834 (5)	0.47474 (13)	0.0339 (5)
C8	0.39388 (8)	0.8608 (5)	0.43985 (14)	0.0352 (5)
C9	0.33228 (7)	0.5996 (5)	0.50282 (16)	0.0354 (5)
H9A	0.3371	0.4853	0.5569	0.042*
H9B	0.3306	0.4673	0.4534	0.042*
C10	0.28326 (7)	0.7629 (5)	0.48906 (15)	0.0342 (5)
H10A	0.2832	0.8755	0.5421	0.041*
H10B	0.2808	0.8974	0.4399	0.041*
C11	0.23799 (7)	0.5690 (5)	0.46968 (15)	0.0341 (5)
H11A	0.2405	0.4329	0.5185	0.041*
H11B	0.2377	0.4583	0.4161	0.041*
C12	0.18917 (7)	0.7341 (5)	0.45715 (15)	0.0346 (5)
H12A	0.1886	0.8336	0.5123	0.042*
H12B	0.1880	0.8803	0.4115	0.042*
C13	0.14296 (7)	0.5478 (5)	0.43108 (15)	0.0347 (5)
H13A	0.1440	0.4011	0.4765	0.042*
H13B	0.1433	0.4492	0.3757	0.042*
C14	0.09459 (7)	0.7159 (5)	0.41929 (15)	0.0359 (5)
H14A	0.0941	0.8117	0.4750	0.043*
H14B	0.0939	0.8651	0.3748	0.043*
C15	0.04810 (7)	0.5345 (5)	0.39165 (15)	0.0364 (5)
H15A	0.0487	0.3850	0.4361	0.044*
H15B	0.0485	0.4391	0.3358	0.044*
C16	0.00019 (7)	0.7038 (5)	0.38033 (15)	0.0373 (5)
H16A	−0.0003	0.8538	0.3361	0.045*
H16B	−0.0001	0.7987	0.4363	0.045*
C17	−0.04666 (7)	0.5241 (5)	0.35234 (15)	0.0376 (5)
H17A	−0.0463	0.3745	0.3967	0.045*
H17B	−0.0463	0.4288	0.2965	0.045*
C18	−0.09460 (7)	0.6944 (5)	0.34082 (16)	0.0377 (5)
H18A	−0.0948	0.7913	0.3965	0.045*
H18B	−0.0951	0.8430	0.2961	0.045*
C19	−0.14159 (7)	0.5157 (6)	0.31364 (16)	0.0386 (5)
H19A	−0.1415	0.4188	0.2579	0.046*
H19B	−0.1411	0.3672	0.3583	0.046*
C20	−0.18930 (8)	0.6862 (6)	0.30219 (16)	0.0390 (5)
H20A	−0.1894	0.7831	0.3579	0.047*
H20B	−0.1897	0.8348	0.2575	0.047*
C21	−0.23622 (8)	0.5095 (6)	0.27508 (17)	0.0447 (6)
H21A	−0.2358	0.3606	0.3196	0.054*
H21B	−0.2363	0.4133	0.2192	0.054*
C22	−0.28379 (8)	0.6818 (7)	0.2641 (2)	0.0543 (7)
H22A	−0.3126	0.5554	0.2469	0.081*
H22B	−0.2850	0.8263	0.2188	0.081*
H22C	−0.2844	0.7747	0.3195	0.081*

	U11	U22	U33	U12	U13	U23
O1	0.0391 (9)	0.0730 (13)	0.0381 (9)	0.0013 (9)	0.0171 (7)	0.0179 (9)
O2	0.0500 (10)	0.0715 (13)	0.0335 (9)	0.0075 (10)	0.0056 (7)	−0.0139 (8)
N1	0.0226 (8)	0.0361 (10)	0.0329 (9)	−0.0005 (7)	0.0045 (7)	−0.0041 (7)
C1	0.0209 (8)	0.0309 (10)	0.0261 (9)	0.0024 (8)	0.0035 (7)	0.0019 (8)
C2	0.0268 (9)	0.0377 (11)	0.0301 (10)	−0.0018 (9)	0.0087 (8)	0.0045 (8)
C3	0.0351 (11)	0.0438 (13)	0.0269 (10)	0.0039 (10)	0.0078 (8)	0.0003 (9)
C4	0.0347 (11)	0.0366 (12)	0.0382 (11)	−0.0014 (10)	0.0023 (9)	−0.0041 (9)
C5	0.0246 (9)	0.0355 (11)	0.0398 (11)	−0.0036 (9)	0.0041 (8)	0.0047 (9)
C6	0.0222 (9)	0.0337 (11)	0.0287 (9)	0.0030 (8)	0.0060 (7)	0.0067 (8)
C7	0.0256 (9)	0.0451 (13)	0.0314 (10)	0.0094 (9)	0.0073 (8)	0.0121 (9)
C8	0.0297 (10)	0.0450 (13)	0.0301 (10)	0.0104 (10)	0.0055 (8)	−0.0007 (9)
C9	0.0223 (9)	0.0332 (11)	0.0478 (12)	−0.0004 (9)	0.0026 (8)	−0.0053 (9)
C10	0.0227 (9)	0.0297 (11)	0.0475 (12)	−0.0006 (8)	0.0030 (9)	−0.0047 (9)
C11	0.0208 (9)	0.0342 (11)	0.0450 (12)	0.0001 (8)	0.0032 (8)	−0.0041 (9)
C12	0.0217 (9)	0.0344 (11)	0.0457 (12)	0.0001 (8)	0.0036 (8)	−0.0026 (9)
C13	0.0208 (9)	0.0390 (12)	0.0423 (11)	−0.0007 (9)	0.0035 (8)	−0.0028 (9)
C14	0.0218 (9)	0.0404 (12)	0.0443 (12)	0.0005 (9)	0.0056 (8)	−0.0012 (10)
C15	0.0220 (9)	0.0432 (13)	0.0425 (12)	−0.0004 (9)	0.0044 (9)	−0.0026 (10)
C16	0.0225 (9)	0.0424 (13)	0.0456 (12)	0.0003 (9)	0.0055 (9)	−0.0017 (10)
C17	0.0225 (9)	0.0447 (13)	0.0439 (12)	−0.0001 (9)	0.0042 (9)	−0.0038 (10)
C18	0.0211 (9)	0.0437 (13)	0.0460 (12)	0.0001 (9)	0.0032 (9)	−0.0012 (10)
C19	0.0228 (9)	0.0474 (14)	0.0442 (12)	0.0003 (9)	0.0050 (9)	−0.0048 (10)
C20	0.0237 (10)	0.0454 (13)	0.0458 (12)	0.0004 (10)	0.0042 (9)	−0.0012 (10)
C21	0.0277 (11)	0.0535 (15)	0.0508 (14)	−0.0028 (11)	0.0052 (10)	−0.0085 (12)
C22	0.0246 (11)	0.0702 (19)	0.0649 (17)	−0.0010 (12)	0.0045 (11)	−0.0017 (15)

O1—C7	1.207 (2)	C13—H13A	0.9900
O2—C8	1.211 (3)	C13—H13B	0.9900
N1—C8	1.371 (3)	C14—C15	1.519 (3)
N1—C1	1.415 (3)	C14—H14A	0.9900
N1—C9	1.455 (3)	C14—H14B	0.9900
C1—C2	1.375 (3)	C15—C16	1.520 (3)
C1—C6	1.399 (3)	C15—H15A	0.9900
C2—C3	1.397 (3)	C15—H15B	0.9900
C2—H2	0.9500	C16—C17	1.523 (3)
C3—C4	1.384 (3)	C16—H16A	0.9900
C3—H3	0.9500	C16—H16B	0.9900
C4—C5	1.393 (3)	C17—C18	1.523 (3)
C4—H4	0.9500	C17—H17A	0.9900
C5—C6	1.381 (3)	C17—H17B	0.9900
C5—H5	0.9500	C18—C19	1.522 (3)
C6—C7	1.460 (3)	C18—H18A	0.9900
C7—C8	1.549 (3)	C18—H18B	0.9900
C9—C10	1.529 (3)	C19—C20	1.519 (3)
C9—H9A	0.9900	C19—H19A	0.9900
C9—H9B	0.9900	C19—H19B	0.9900
C10—C11	1.521 (3)	C20—C21	1.516 (3)
C10—H10A	0.9900	C20—H20A	0.9900
C10—H10B	0.9900	C20—H20B	0.9900
C11—C12	1.530 (3)	C21—C22	1.520 (3)
C11—H11A	0.9900	C21—H21A	0.9900
C11—H11B	0.9900	C21—H21B	0.9900
C12—C13	1.524 (3)	C22—H22A	0.9800
C12—H12A	0.9900	C22—H22B	0.9800
C12—H12B	0.9900	C22—H22C	0.9800
C13—C14	1.527 (3)
C8—N1—C1	110.78 (17)	H13A—C13—H13B	107.8
C8—N1—C9	123.48 (18)	C15—C14—C13	113.71 (19)
C1—N1—C9	125.31 (17)	C15—C14—H14A	108.8
C2—C1—C6	121.43 (19)	C13—C14—H14A	108.8
C2—C1—N1	128.04 (18)	C15—C14—H14B	108.8
C6—C1—N1	110.53 (16)	C13—C14—H14B	108.8
C1—C2—C3	117.06 (19)	H14A—C14—H14B	107.7
C1—C2—H2	121.5	C14—C15—C16	113.3 (2)
C3—C2—H2	121.5	C14—C15—H15A	108.9
C4—C3—C2	122.05 (19)	C16—C15—H15A	108.9
C4—C3—H3	119.0	C14—C15—H15B	108.9
C2—C3—H3	119.0	C16—C15—H15B	108.9
C3—C4—C5	120.3 (2)	H15A—C15—H15B	107.7
C3—C4—H4	119.8	C15—C16—C17	113.7 (2)
C5—C4—H4	119.8	C15—C16—H16A	108.8
C6—C5—C4	118.04 (19)	C17—C16—H16A	108.8
C6—C5—H5	121.0	C15—C16—H16B	108.8
C4—C5—H5	121.0	C17—C16—H16B	108.8
C5—C6—C1	121.07 (18)	H16A—C16—H16B	107.7
C5—C6—C7	131.52 (19)	C16—C17—C18	113.6 (2)
C1—C6—C7	107.41 (18)	C16—C17—H17A	108.8
O1—C7—C6	131.3 (2)	C18—C17—H17A	108.8
O1—C7—C8	123.5 (2)	C16—C17—H17B	108.8
C6—C7—C8	105.27 (16)	C18—C17—H17B	108.8
O2—C8—N1	126.5 (2)	H17A—C17—H17B	107.7
O2—C8—C7	127.5 (2)	C19—C18—C17	113.9 (2)
N1—C8—C7	105.93 (17)	C19—C18—H18A	108.8
N1—C9—C10	111.84 (18)	C17—C18—H18A	108.8
N1—C9—H9A	109.2	C19—C18—H18B	108.8
C10—C9—H9A	109.2	C17—C18—H18B	108.8
N1—C9—H9B	109.2	H18A—C18—H18B	107.7
C10—C9—H9B	109.2	C20—C19—C18	113.7 (2)
H9A—C9—H9B	107.9	C20—C19—H19A	108.8
C11—C10—C9	112.80 (18)	C18—C19—H19A	108.8
C11—C10—H10A	109.0	C20—C19—H19B	108.8
C9—C10—H10A	109.0	C18—C19—H19B	108.8
C11—C10—H10B	109.0	H19A—C19—H19B	107.7
C9—C10—H10B	109.0	C21—C20—C19	114.0 (2)
H10A—C10—H10B	107.8	C21—C20—H20A	108.8
C10—C11—C12	112.39 (18)	C19—C20—H20A	108.8
C10—C11—H11A	109.1	C21—C20—H20B	108.8
C12—C11—H11A	109.1	C19—C20—H20B	108.8
C10—C11—H11B	109.1	H20A—C20—H20B	107.7
C12—C11—H11B	109.1	C20—C21—C22	113.6 (2)
H11A—C11—H11B	107.9	C20—C21—H21A	108.8
C13—C12—C11	113.66 (19)	C22—C21—H21A	108.8
C13—C12—H12A	108.8	C20—C21—H21B	108.8
C11—C12—H12A	108.8	C22—C21—H21B	108.8
C13—C12—H12B	108.8	H21A—C21—H21B	107.7
C11—C12—H12B	108.8	C21—C22—H22A	109.5
H12A—C12—H12B	107.7	C21—C22—H22B	109.5
C12—C13—C14	112.95 (19)	H22A—C22—H22B	109.5
C12—C13—H13A	109.0	C21—C22—H22C	109.5
C14—C13—H13A	109.0	H22A—C22—H22C	109.5
C12—C13—H13B	109.0	H22B—C22—H22C	109.5
C14—C13—H13B	109.0
C8—N1—C1—C2	178.1 (2)	C1—N1—C8—C7	2.6 (2)
C9—N1—C1—C2	5.4 (3)	C9—N1—C8—C7	175.52 (18)
C8—N1—C1—C6	−1.6 (2)	O1—C7—C8—O2	−2.9 (4)
C9—N1—C1—C6	−174.36 (18)	C6—C7—C8—O2	175.9 (2)
C6—C1—C2—C3	0.9 (3)	O1—C7—C8—N1	178.6 (2)
N1—C1—C2—C3	−178.8 (2)	C6—C7—C8—N1	−2.7 (2)
C1—C2—C3—C4	−0.4 (3)	C8—N1—C9—C10	−94.4 (2)
C2—C3—C4—C5	−0.5 (3)	C1—N1—C9—C10	77.5 (3)
C3—C4—C5—C6	0.9 (3)	N1—C9—C10—C11	172.23 (18)
C4—C5—C6—C1	−0.4 (3)	C9—C10—C11—C12	179.29 (19)
C4—C5—C6—C7	178.9 (2)	C10—C11—C12—C13	175.77 (19)
C2—C1—C6—C5	−0.5 (3)	C11—C12—C13—C14	179.72 (19)
N1—C1—C6—C5	179.22 (19)	C12—C13—C14—C15	178.93 (19)
C2—C1—C6—C7	−179.99 (19)	C13—C14—C15—C16	179.85 (19)
N1—C1—C6—C7	−0.3 (2)	C14—C15—C16—C17	179.82 (19)
C5—C6—C7—O1	1.0 (4)	C15—C16—C17—C18	−179.84 (19)
C1—C6—C7—O1	−179.6 (2)	C16—C17—C18—C19	−179.47 (19)
C5—C6—C7—C8	−177.6 (2)	C17—C18—C19—C20	−179.98 (19)
C1—C6—C7—C8	1.8 (2)	C18—C19—C20—C21	180.0 (2)
C1—N1—C8—O2	−176.0 (2)	C19—C20—C21—C22	179.8 (2)
C9—N1—C8—O2	−3.1 (3)