Tris{2-[(2,6-dimethyl-phen-yl)amino]-eth-yl}amine.

The title compound, C(30)H(42)N(4), is an aryl-ated tris-(amino-eth-yl)amine derivative which was obtained by reducing the corresponding tris-amide with AlH(3). The asymmetric unit consists of one third of a C(3v)-symmetric mol-ecule with the tertiary N atom lying on a crystallographic threefold axis.

Related literature

For the structural parameters of aryl­ated derivatives of tris­(amino­eth­yl)amine, see: Almesåker et al. (2009 ▶); Amoroso et al. (2009 ▶). For the synthesis and the structural parameters of metal complexes based on aryl­ated derivatives of tris­(amino­eth­yl)amine, see: Morton et al. (2000 ▶); Yandulov & Schrock (2005 ▶); Smythe et al. (2006 ▶); Reithofer et al. (2010 ▶); Almesåker et al. (2010 ▶).

Experimental

Crystal data

C30H42N4

M = 458.68

Trigonal,

a = 14.2880 (7) Å

c = 22.3811 (11) Å

V = 3956.9 (5) Å3

Z = 6

Mo Kα radiation

μ = 0.07 mm−1

T = 100 K

0.1 × 0.1 × 0.1 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2009 ▶) T min = 0.680, T max = 0.746

20390 measured reflections

2695 independent reflections

2330 reflections with I > 2σ(I)

R int = 0.031

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.113

S = 1.06

2695 reflections

109 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.42 e Å−3

Δρmin = −0.18 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); 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 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811049397/zl2430sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811049397/zl2430Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811049397/zl2430Isup3.cml

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

C30H42N4	Dx = 1.155 Mg m−3
Mr = 458.68	Mo Kα radiation, λ = 0.71073 Å
Trigonal, R3	Cell parameters from 9944 reflections
Hall symbol: -R 3	θ = 2.5–30.6°
a = 14.2880 (7) Å	µ = 0.07 mm−1
c = 22.3811 (11) Å	T = 100 K
V = 3956.9 (5) Å3	Block, colourless
Z = 6	0.1 × 0.1 × 0.1 mm
F(000) = 1500

Bruker Smart APEXII CCD diffractometer	2695 independent reflections
Radiation source: ImuS micro-focus sealed tube	2330 reflections with I > 2σ(I)
Icoatech ImuS multilayer optics	Rint = 0.031
Detector resolution: 8.3 pixels mm-1	θmax = 30.6°, θmin = 1.9°
φ and ω scans	h = −20→20
Absorption correction: multi-scan (SADABS; Sheldrick, 2009)	k = −20→20
Tmin = 0.680, Tmax = 0.746	l = −31→31
20390 measured reflections

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.113	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ2(Fo2) + (0.0529P)2 + 4.1067P] where P = (Fo2 + 2Fc2)/3
2695 reflections	(Δ/σ)max < 0.001
109 parameters	Δρmax = 0.42 e Å−3
0 restraints	Δρmin = −0.18 e Å−3

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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.

	x	y	z	Uiso*/Ueq
C1	0.58018 (7)	0.22760 (7)	0.11134 (4)	0.01668 (18)
H1A	0.5860	0.2233	0.0675	0.020*
H1B	0.5095	0.2218	0.1200	0.020*
C2	0.58289 (8)	0.13268 (7)	0.13995 (4)	0.01696 (18)
H2A	0.5189	0.0642	0.1271	0.020*
H2B	0.6485	0.1316	0.1268	0.020*
C3	0.58132 (7)	0.05566 (7)	0.23806 (4)	0.01446 (17)
C4	0.48468 (7)	−0.04409 (7)	0.24161 (4)	0.01604 (18)
C5	0.48377 (8)	−0.12750 (8)	0.27456 (4)	0.01872 (19)
H5	0.4192	−0.1956	0.2766	0.022*
C6	0.57519 (8)	−0.11311 (8)	0.30435 (4)	0.01925 (19)
H6	0.5732	−0.1708	0.3264	0.023*
C7	0.66954 (8)	−0.01359 (8)	0.30156 (4)	0.01794 (18)
H7	0.7318	−0.0032	0.3225	0.022*
C8	0.67430 (7)	0.07137 (7)	0.26845 (4)	0.01593 (18)
C9	0.38314 (8)	−0.06114 (8)	0.21179 (5)	0.0221 (2)
H9A	0.3838	−0.0794	0.1696	0.033*
H9B	0.3791	0.0052	0.2146	0.033*
H9C	0.3202	−0.1203	0.2316	0.033*
C10	0.77793 (8)	0.17807 (8)	0.26578 (5)	0.0238 (2)
H10A	0.8351	0.1721	0.2866	0.036*
H10B	0.7675	0.2338	0.2850	0.036*
H10C	0.7988	0.1979	0.2240	0.036*
N1	0.6667	0.3333	0.13202 (6)	0.0142 (2)
N2	0.58312 (7)	0.14184 (6)	0.20523 (4)	0.01647 (17)
H2N	0.6392 (12)	0.2043 (12)	0.2164 (6)	0.024 (3)*

	U11	U22	U33	U12	U13	U23
C1	0.0167 (4)	0.0151 (4)	0.0166 (4)	0.0067 (3)	−0.0036 (3)	−0.0003 (3)
C2	0.0202 (4)	0.0147 (4)	0.0158 (4)	0.0086 (3)	−0.0020 (3)	−0.0008 (3)
C3	0.0160 (4)	0.0149 (4)	0.0142 (4)	0.0090 (3)	−0.0006 (3)	−0.0009 (3)
C4	0.0154 (4)	0.0168 (4)	0.0159 (4)	0.0081 (3)	−0.0001 (3)	−0.0016 (3)
C5	0.0195 (4)	0.0153 (4)	0.0201 (4)	0.0077 (3)	0.0034 (3)	0.0007 (3)
C6	0.0240 (4)	0.0184 (4)	0.0196 (4)	0.0137 (4)	0.0037 (3)	0.0036 (3)
C7	0.0191 (4)	0.0216 (4)	0.0173 (4)	0.0133 (4)	−0.0003 (3)	0.0011 (3)
C8	0.0155 (4)	0.0164 (4)	0.0160 (4)	0.0081 (3)	−0.0008 (3)	−0.0007 (3)
C9	0.0149 (4)	0.0237 (5)	0.0238 (5)	0.0068 (4)	−0.0031 (3)	−0.0002 (4)
C10	0.0176 (4)	0.0201 (4)	0.0286 (5)	0.0055 (4)	−0.0063 (4)	0.0024 (4)
N1	0.0130 (3)	0.0130 (3)	0.0167 (6)	0.00651 (17)	0.000	0.000
N2	0.0204 (4)	0.0139 (3)	0.0158 (4)	0.0091 (3)	−0.0030 (3)	−0.0011 (3)

C1—N1	1.4686 (10)	C6—C7	1.3879 (14)
C1—C2	1.5178 (12)	C6—H6	0.9500
C1—H1A	0.9900	C7—C8	1.3946 (12)
C1—H1B	0.9900	C7—H7	0.9500
C2—N2	1.4667 (12)	C8—C10	1.5043 (13)
C2—H2A	0.9900	C9—H9A	0.9800
C2—H2B	0.9900	C9—H9B	0.9800
C3—C4	1.4059 (12)	C9—H9C	0.9800
C3—C8	1.4069 (12)	C10—H10A	0.9800
C3—N2	1.4231 (11)	C10—H10B	0.9800
C4—C5	1.3961 (13)	C10—H10C	0.9800
C4—C9	1.5020 (13)	N1—C1i	1.4686 (10)
C5—C6	1.3872 (14)	N1—C1ii	1.4686 (10)
C5—H5	0.9500	N2—H2N	0.886 (15)
N1—C1—C2	113.69 (7)	C6—C7—C8	121.01 (9)
N1—C1—H1A	108.8	C6—C7—H7	119.5
C2—C1—H1A	108.8	C8—C7—H7	119.5
N1—C1—H1B	108.8	C7—C8—C3	119.13 (8)
C2—C1—H1B	108.8	C7—C8—C10	119.87 (8)
H1A—C1—H1B	107.7	C3—C8—C10	120.99 (8)
N2—C2—C1	109.91 (7)	C4—C9—H9A	109.5
N2—C2—H2A	109.7	C4—C9—H9B	109.5
C1—C2—H2A	109.7	H9A—C9—H9B	109.5
N2—C2—H2B	109.7	C4—C9—H9C	109.5
C1—C2—H2B	109.7	H9A—C9—H9C	109.5
H2A—C2—H2B	108.2	H9B—C9—H9C	109.5
C4—C3—C8	120.33 (8)	C8—C10—H10A	109.5
C4—C3—N2	119.34 (8)	C8—C10—H10B	109.5
C8—C3—N2	120.30 (8)	H10A—C10—H10B	109.5
C5—C4—C3	118.71 (8)	C8—C10—H10C	109.5
C5—C4—C9	120.02 (8)	H10A—C10—H10C	109.5
C3—C4—C9	121.26 (8)	H10B—C10—H10C	109.5
C6—C5—C4	121.41 (9)	C1i—N1—C1	110.54 (6)
C6—C5—H5	119.3	C1i—N1—C1ii	110.54 (6)
C4—C5—H5	119.3	C1—N1—C1ii	110.54 (6)
C5—C6—C7	119.38 (9)	C3—N2—C2	116.04 (7)
C5—C6—H6	120.3	C3—N2—H2N	110.0 (9)
C7—C6—H6	120.3	C2—N2—H2N	109.3 (9)
N1—C1—C2—N2	54.02 (10)	C6—C7—C8—C10	−179.46 (9)
C8—C3—C4—C5	−1.51 (13)	C4—C3—C8—C7	0.65 (13)
N2—C3—C4—C5	−179.24 (8)	N2—C3—C8—C7	178.35 (8)
C8—C3—C4—C9	177.26 (8)	C4—C3—C8—C10	−179.19 (9)
N2—C3—C4—C9	−0.47 (13)	N2—C3—C8—C10	−1.48 (14)
C3—C4—C5—C6	1.07 (14)	C2—C1—N1—C1i	67.79 (13)
C9—C4—C5—C6	−177.72 (9)	C2—C1—N1—C1ii	−169.49 (8)
C4—C5—C6—C7	0.25 (14)	C4—C3—N2—C2	−74.71 (11)
C5—C6—C7—C8	−1.16 (14)	C8—C3—N2—C2	107.56 (10)
C6—C7—C8—C3	0.70 (14)	C1—C2—N2—C3	177.64 (7)