2-(1H-Indol-3-yl)-4,4,5,5-tetra-methyl-imidazolidine-1-oxyl 3-oxide.

In the title compound, C(15)H(18)N(3)O(2), the plane of the indole ring system is twisted with respect to the plane of the nitronyl nitroxide moiety, exhibiting a dihedral angle of 21.61 (6)°. The crystal packing is stabilized by N-H⋯O hydrogen bonds and weak C-H⋯O inter-actions.

Related literature

For the preparation of nitronyl nitroxides, see: Ullman et al. (1974 ▶). For their biological activity, see: Soule et al. (2007 ▶) and their coordination properties, see: Masuda et al. (2009 ▶). For related structures, see: Iqbal et al. (2009 ▶); Qin et al. (2009 ▶); Tanaka et al. (2007 ▶).

Experimental

Crystal data

C15H18N3O2

M = 272.32

Orthorhombic,

a = 15.0810 (15) Å

b = 8.7700 (8) Å

c = 10.6108 (10) Å

V = 1403.4 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 296 K

0.37 × 0.29 × 0.18 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2007 ▶) T min = 0.968, T max = 0.984

6651 measured reflections

1323 independent reflections

1208 reflections with I > 2σ(I)

R int = 0.023

Refinement

R[F 2 > 2σ(F 2)] = 0.025

wR(F 2) = 0.067

S = 1.06

1323 reflections

186 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.13 e Å−3

Δρmin = −0.09 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and DIAMOND (Brandenburg, 1998 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810002175/fl2283sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810002175/fl2283Isup2.hkl

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

C15H18N3O2	F(000) = 580
Mr = 272.32	Dx = 1.289 Mg m−3
Orthorhombic, Pca21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2ac	Cell parameters from 2598 reflections
a = 15.0810 (15) Å	θ = 2.7–24.4°
b = 8.7700 (8) Å	µ = 0.09 mm−1
c = 10.6108 (10) Å	T = 296 K
V = 1403.4 (2) Å3	Block, blue
Z = 4	0.37 × 0.29 × 0.18 mm

Bruker APEXII CCD area-detector diffractometer	1323 independent reflections
Radiation source: fine-focus sealed tube	1208 reflections with I > 2σ(I)
graphite	Rint = 0.023
phi and ω scans	θmax = 25.1°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2007)	h = −14→17
Tmin = 0.968, Tmax = 0.984	k = −8→10
6651 measured reflections	l = −12→12

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.025	H-atom parameters constrained
wR(F2) = 0.067	w = 1/[σ2(Fo2) + (0.0394P)2 + 0.1053P] where P = (Fo2 + 2Fc2)/3
S = 1.06	(Δ/σ)max < 0.001
1323 reflections	Δρmax = 0.13 e Å−3
186 parameters	Δρmin = −0.09 e Å−3
1 restraint	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0146 (19)

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.we could not determine the absolute configuration,because there is no atom heavier than Si in the molecular

	x	y	z	Uiso*/Ueq
N1	−0.01319 (14)	1.0261 (2)	0.9413 (2)	0.0605 (5)
H1	−0.0087	1.0928	1.0004	0.073*
N2	0.11909 (10)	0.60749 (18)	0.83997 (15)	0.0393 (4)
N3	0.05128 (10)	0.62465 (17)	0.65920 (15)	0.0381 (4)
O1	0.14925 (11)	0.64081 (18)	0.94892 (14)	0.0579 (4)
O2	0.01465 (11)	0.68277 (17)	0.56075 (14)	0.0545 (4)
C1	−0.08282 (15)	1.0156 (2)	0.8579 (2)	0.0534 (6)
C2	−0.16017 (18)	1.1028 (3)	0.8506 (3)	0.0731 (8)
H2	−0.1707	1.1825	0.9064	0.088*
C3	−0.21965 (16)	1.0666 (3)	0.7587 (4)	0.0795 (9)
H3	−0.2715	1.1234	0.7516	0.095*
C4	−0.20480 (15)	0.9465 (3)	0.6750 (3)	0.0692 (7)
H4	−0.2463	0.9255	0.6126	0.083*
C5	−0.12892 (14)	0.8583 (2)	0.6839 (2)	0.0529 (6)
H5	−0.1201	0.7769	0.6292	0.063*
C6	−0.06560 (13)	0.8930 (2)	0.7760 (2)	0.0442 (5)
C7	0.01895 (13)	0.8304 (2)	0.81520 (18)	0.0407 (5)
C8	0.04679 (15)	0.9165 (2)	0.9167 (2)	0.0515 (5)
H8	0.0991	0.9010	0.9614	0.062*
C9	0.06218 (12)	0.6932 (2)	0.77161 (18)	0.0363 (4)
C10	0.15347 (12)	0.4734 (2)	0.76668 (19)	0.0385 (4)
C11	0.24518 (16)	0.5183 (2)	0.7176 (2)	0.0523 (5)
H11A	0.2395	0.6018	0.6597	0.079*
H11B	0.2715	0.4328	0.6752	0.079*
H11C	0.2821	0.5483	0.7870	0.079*
C12	0.15962 (15)	0.3356 (2)	0.8531 (2)	0.0516 (5)
H12A	0.2043	0.3532	0.9158	0.077*
H12B	0.1749	0.2471	0.8045	0.077*
H12C	0.1035	0.3195	0.8936	0.077*
C13	0.08199 (13)	0.4624 (2)	0.66190 (19)	0.0381 (4)
C14	0.00154 (14)	0.3668 (2)	0.6989 (2)	0.0516 (5)
H14A	−0.0183	0.3965	0.7813	0.077*
H14B	0.0176	0.2609	0.6997	0.077*
H14C	−0.0453	0.3829	0.6391	0.077*
C15	0.11578 (16)	0.4160 (3)	0.5331 (2)	0.0556 (6)
H15A	0.0674	0.4150	0.4743	0.083*
H15B	0.1415	0.3161	0.5379	0.083*
H15C	0.1598	0.4876	0.5054	0.083*

	U11	U22	U33	U12	U13	U23
N1	0.0810 (13)	0.0386 (10)	0.0620 (12)	0.0000 (9)	0.0137 (11)	−0.0174 (10)
N2	0.0440 (9)	0.0423 (8)	0.0315 (8)	−0.0009 (7)	0.0003 (7)	−0.0031 (7)
N3	0.0481 (9)	0.0330 (8)	0.0333 (8)	0.0030 (7)	−0.0032 (7)	0.0023 (7)
O1	0.0670 (9)	0.0679 (10)	0.0389 (8)	0.0047 (7)	−0.0128 (7)	−0.0112 (8)
O2	0.0774 (10)	0.0452 (8)	0.0407 (8)	0.0126 (7)	−0.0113 (8)	0.0051 (6)
C1	0.0613 (13)	0.0344 (11)	0.0644 (15)	−0.0023 (9)	0.0182 (12)	−0.0009 (10)
C2	0.0771 (18)	0.0385 (12)	0.104 (2)	0.0098 (11)	0.0325 (17)	0.0013 (14)
C3	0.0534 (14)	0.0547 (14)	0.130 (3)	0.0105 (11)	0.0192 (18)	0.0178 (18)
C4	0.0492 (13)	0.0600 (14)	0.098 (2)	−0.0007 (11)	0.0023 (14)	0.0130 (15)
C5	0.0485 (11)	0.0439 (11)	0.0663 (15)	−0.0032 (9)	0.0053 (11)	0.0049 (11)
C6	0.0487 (10)	0.0304 (10)	0.0535 (12)	−0.0032 (8)	0.0117 (10)	0.0034 (9)
C7	0.0485 (11)	0.0329 (10)	0.0406 (11)	−0.0040 (8)	0.0070 (8)	−0.0021 (8)
C8	0.0614 (13)	0.0411 (11)	0.0520 (13)	−0.0036 (10)	0.0062 (11)	−0.0070 (10)
C9	0.0405 (9)	0.0333 (9)	0.0351 (10)	−0.0032 (8)	0.0014 (8)	0.0005 (9)
C10	0.0418 (10)	0.0375 (10)	0.0363 (9)	0.0025 (7)	0.0029 (8)	0.0009 (9)
C11	0.0440 (10)	0.0571 (12)	0.0560 (12)	−0.0003 (10)	0.0081 (10)	−0.0009 (12)
C12	0.0584 (13)	0.0488 (12)	0.0474 (12)	0.0065 (9)	−0.0017 (10)	0.0091 (11)
C13	0.0464 (10)	0.0323 (9)	0.0357 (9)	0.0031 (8)	0.0015 (8)	−0.0008 (8)
C14	0.0540 (11)	0.0415 (11)	0.0592 (13)	−0.0070 (9)	−0.0065 (11)	−0.0003 (10)
C15	0.0734 (15)	0.0521 (12)	0.0412 (12)	0.0127 (11)	0.0007 (11)	−0.0085 (10)

N1—C8	1.346 (3)	C7—C8	1.381 (3)
N1—C1	1.377 (3)	C7—C9	1.444 (3)
N1—H1	0.8600	C8—H8	0.9300
N2—O1	1.276 (2)	C10—C12	1.519 (3)
N2—C9	1.352 (2)	C10—C11	1.529 (3)
N2—C10	1.502 (2)	C10—C13	1.552 (3)
N3—O2	1.287 (2)	C11—H11A	0.9600
N3—C9	1.346 (2)	C11—H11B	0.9600
N3—C13	1.496 (2)	C11—H11C	0.9600
C1—C2	1.397 (3)	C12—H12A	0.9600
C1—C6	1.407 (3)	C12—H12B	0.9600
C2—C3	1.362 (5)	C12—H12C	0.9600
C2—H2	0.9300	C13—C15	1.515 (3)
C3—C4	1.396 (4)	C13—C14	1.526 (3)
C3—H3	0.9300	C14—H14A	0.9600
C4—C5	1.384 (3)	C14—H14B	0.9600
C4—H4	0.9300	C14—H14C	0.9600
C5—C6	1.400 (3)	C15—H15A	0.9600
C5—H5	0.9300	C15—H15B	0.9600
C6—C7	1.449 (3)	C15—H15C	0.9600
C8—N1—C1	109.91 (19)	N2—C10—C12	109.33 (16)
C8—N1—H1	125.0	N2—C10—C11	106.68 (15)
C1—N1—H1	125.0	C12—C10—C11	110.80 (17)
O1—N2—C9	125.79 (16)	N2—C10—C13	100.34 (14)
O1—N2—C10	121.68 (16)	C12—C10—C13	115.19 (16)
C9—N2—C10	112.14 (16)	C11—C10—C13	113.58 (17)
O2—N3—C9	126.49 (15)	C10—C11—H11A	109.5
O2—N3—C13	121.66 (15)	C10—C11—H11B	109.5
C9—N3—C13	111.73 (15)	H11A—C11—H11B	109.5
N1—C1—C2	129.5 (2)	C10—C11—H11C	109.5
N1—C1—C6	107.89 (19)	H11A—C11—H11C	109.5
C2—C1—C6	122.6 (3)	H11B—C11—H11C	109.5
C3—C2—C1	117.5 (3)	C10—C12—H12A	109.5
C3—C2—H2	121.2	C10—C12—H12B	109.5
C1—C2—H2	121.2	H12A—C12—H12B	109.5
C2—C3—C4	121.7 (2)	C10—C12—H12C	109.5
C2—C3—H3	119.2	H12A—C12—H12C	109.5
C4—C3—H3	119.2	H12B—C12—H12C	109.5
C5—C4—C3	120.7 (3)	N3—C13—C15	110.02 (16)
C5—C4—H4	119.6	N3—C13—C14	106.34 (15)
C3—C4—H4	119.6	C15—C13—C14	110.62 (19)
C4—C5—C6	119.3 (2)	N3—C13—C10	99.78 (14)
C4—C5—H5	120.3	C15—C13—C10	115.44 (17)
C6—C5—H5	120.3	C14—C13—C10	113.69 (17)
C5—C6—C1	118.12 (19)	C13—C14—H14A	109.5
C5—C6—C7	135.90 (19)	C13—C14—H14B	109.5
C1—C6—C7	105.97 (19)	H14A—C14—H14B	109.5
C8—C7—C9	124.61 (19)	C13—C14—H14C	109.5
C8—C7—C6	106.51 (17)	H14A—C14—H14C	109.5
C9—C7—C6	128.38 (18)	H14B—C14—H14C	109.5
N1—C8—C7	109.7 (2)	C13—C15—H15A	109.5
N1—C8—H8	125.1	C13—C15—H15B	109.5
C7—C8—H8	125.1	H15A—C15—H15B	109.5
N3—C9—N2	107.72 (15)	C13—C15—H15C	109.5
N3—C9—C7	126.94 (17)	H15A—C15—H15C	109.5
N2—C9—C7	125.30 (17)	H15B—C15—H15C	109.5
C8—N1—C1—C2	178.2 (2)	C10—N2—C9—C7	−179.20 (17)
C8—N1—C1—C6	−0.2 (2)	C8—C7—C9—N3	−163.74 (19)
N1—C1—C2—C3	−179.1 (2)	C6—C7—C9—N3	25.5 (3)
C6—C1—C2—C3	−0.9 (4)	C8—C7—C9—N2	18.9 (3)
C1—C2—C3—C4	0.4 (4)	C6—C7—C9—N2	−151.90 (19)
C2—C3—C4—C5	0.8 (4)	O1—N2—C10—C12	45.8 (2)
C3—C4—C5—C6	−1.6 (4)	C9—N2—C10—C12	−141.06 (17)
C4—C5—C6—C1	1.1 (3)	O1—N2—C10—C11	−74.1 (2)
C4—C5—C6—C7	179.4 (2)	C9—N2—C10—C11	99.07 (18)
N1—C1—C6—C5	178.64 (19)	O1—N2—C10—C13	167.26 (16)
C2—C1—C6—C5	0.1 (3)	C9—N2—C10—C13	−19.56 (19)
N1—C1—C6—C7	−0.1 (2)	O2—N3—C13—C15	34.2 (3)
C2—C1—C6—C7	−178.6 (2)	C9—N3—C13—C15	−149.50 (18)
C5—C6—C7—C8	−178.0 (2)	O2—N3—C13—C14	−85.6 (2)
C1—C6—C7—C8	0.4 (2)	C9—N3—C13—C14	90.7 (2)
C5—C6—C7—C9	−6.0 (4)	O2—N3—C13—C10	155.98 (16)
C1—C6—C7—C9	172.47 (19)	C9—N3—C13—C10	−27.72 (19)
C1—N1—C8—C7	0.5 (2)	N2—C10—C13—N3	25.95 (17)
C9—C7—C8—N1	−172.98 (19)	C12—C10—C13—N3	143.19 (16)
C6—C7—C8—N1	−0.5 (2)	C11—C10—C13—N3	−87.50 (18)
O2—N3—C9—N2	−167.34 (17)	N2—C10—C13—C15	143.77 (17)
C13—N3—C9—N2	16.6 (2)	C12—C10—C13—C15	−99.0 (2)
O2—N3—C9—C7	14.9 (3)	C11—C10—C13—C15	30.3 (2)
C13—N3—C9—C7	−161.20 (17)	N2—C10—C13—C14	−86.84 (18)
O1—N2—C9—N3	175.82 (17)	C12—C10—C13—C14	30.4 (2)
C10—N2—C9—N3	3.0 (2)	C11—C10—C13—C14	159.70 (17)
O1—N2—C9—C7	−6.4 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2i	0.86	2.07	2.8506 (18)	150
C12—H12C···O2ii	0.96	2.51	3.434 (2)	161
C14—H14C···O1iii	0.96	2.56	3.495 (2)	164

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O2i	0.86	2.07	2.8506 (18)	150
C12—H12C⋯O2ii	0.96	2.51	3.434 (2)	161
C14—H14C⋯O1iii	0.96	2.56	3.495 (2)	164

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