N,N'-Dineopentyl-naphthalene-1,8-diamine.

In the title compound, C(20)H(30)N(2), all bond distances and angles fall within the usual ranges but the C(ipso)-N distances [1.391 (5) and 1.398 (4) Å] are slightly shorter than the corresponding typical average distance of 1.42 (3) Å. The N atoms may be described as pyramidal sp(3)-hybridized with an N-H⋯H-N separation of 2.07 (2) Å. This is necessitated because the two C(bridgehead)-C(ipso)-N-C torsion angles [170.6 (4) and 172.6 (3)°] would require the amine H atoms to be in prohibitively close proximity if the N atoms were assumed to be sp(2)-hybridized.

Related literature

For the use of 1,8-bis­(diamido)naphthalene (DAN) ligands in the preparation of thermally stable N-heterocyclic carbenes, germylenes and stannylenes, see: Avent et al. (2004 ▶); Bazinet et al. (2001a ▶,b ▶, 2003 ▶, 2007 ▶). For our studies on N-heterocyclic silylenes, see: Hill et al. (2005 ▶); Li et al. (2006 ▶); Naka et al. (2004 ▶). For DAN ligands in transition metal coordination chemistry, see: Lavoie et al. (2007 ▶); Bazinet et al. (2001b ▶). Their titanium and zirconium complexes have been found to be effective catalysts for olefin polymerization, see: Lee et al. (2001 ▶). For a description of the Cambridge Structural Database, see: Allen (2002 ▶). For geometrical analysis, see: Bruno et al. (2002 ▶). For the preparation of the title compound, see: Daniele et al. (2001 ▶).

Experimental

Crystal data

C20H30N2

M = 298.46

Orthorhombic,

a = 6.0425 (14) Å

b = 16.196 (3) Å

c = 18.861 (4) Å

V = 1845.8 (7) Å3

Z = 4

Mo Kα radiation

μ = 0.06 mm−1

T = 300 K

0.70 × 0.30 × 0.20 mm

Data collection

Bruker SMART X2S diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.958, T max = 0.988

12752 measured reflections

2042 independent reflections

1203 reflections with I > 2σ(I)

R int = 0.090

Refinement

R[F 2 > 2σ(F 2)] = 0.053

wR(F 2) = 0.140

S = 0.93

2042 reflections

213 parameters

6 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.12 e Å−3

Δρmin = −0.13 e Å−3

Data collection: GIS (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL and OLEX2 (Dolomanov et al., 2009 ▶); molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL, publCIF (Westrip, 2009 ▶) and modiCIFer (Guzei, 2007 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809050867/zs2021sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809050867/zs2021Isup2.hkl

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

C20H30N2	F(000) = 656
Mr = 298.46	Dx = 1.074 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 1989 reflections
a = 6.0425 (14) Å	θ = 2.5–20.6°
b = 16.196 (3) Å	µ = 0.06 mm−1
c = 18.861 (4) Å	T = 300 K
V = 1845.8 (7) Å3	Needle, yellow
Z = 4	0.70 × 0.30 × 0.20 mm

Bruker SMART X2S diffractometer	2042 independent reflections
Radiation source: micro-focus sealed tube	1203 reflections with I > 2σ(I)
doubly curved silicon crystal	Rint = 0.090
ω scans	θmax = 25.7°, θmin = 2.5°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −7→7
Tmin = 0.958, Tmax = 0.988	k = −19→15
12752 measured reflections	l = −22→22

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)] = 0.053	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.140	H atoms treated by a mixture of independent and constrained refinement
S = 0.93	w = 1/[σ2(Fo2) + (0.079P)2] where P = (Fo2 + 2Fc2)/3
2042 reflections	(Δ/σ)max < 0.001
213 parameters	Δρmax = 0.12 e Å−3
6 restraints	Δρmin = −0.13 e Å−3

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.

	x	y	z	Uiso*/Ueq
N1	0.3691 (7)	0.6434 (2)	0.30061 (17)	0.0693 (11)
H1	0.309 (10)	0.5953 (17)	0.299 (2)	0.16 (3)*
N2	0.2799 (6)	0.55146 (19)	0.41609 (17)	0.0513 (8)
H2	0.396 (2)	0.578 (2)	0.404 (2)	0.13 (2)*
C1	0.7600 (7)	0.5450 (3)	0.2652 (2)	0.0726 (12)
H1C	0.8605	0.5866	0.2818	0.109*
H1A	0.8424	0.4997	0.2456	0.109*
H1B	0.6714	0.5256	0.3040	0.109*
C2	0.7503 (10)	0.6090 (3)	0.1446 (2)	0.1015 (18)
H2C	0.8566	0.6493	0.1599	0.152*
H2B	0.6562	0.6328	0.1091	0.152*
H2A	0.8262	0.5621	0.1252	0.152*
C3	0.4470 (9)	0.5158 (3)	0.1828 (2)	0.0908 (16)
H3A	0.5274	0.4699	0.1633	0.136*
H3C	0.3521	0.5387	0.1471	0.136*
H3B	0.3592	0.4972	0.2221	0.136*
C4	0.6097 (7)	0.5816 (2)	0.20806 (19)	0.0543 (10)
C5	0.4883 (9)	0.6577 (3)	0.2348 (2)	0.0725 (13)
H5B	0.5946	0.7018	0.2421	0.087*
H5A	0.3844	0.6758	0.1988	0.087*
C6	0.2063 (6)	0.6975 (2)	0.32437 (18)	0.0467 (10)
C7	0.1708 (8)	0.7721 (2)	0.2898 (2)	0.0649 (12)
H7	0.2658	0.7881	0.2535	0.078*
C8	−0.0050 (9)	0.8235 (3)	0.3087 (2)	0.0762 (14)
H8	−0.0252	0.8730	0.2846	0.091*
C9	−0.1462 (8)	0.8027 (2)	0.3611 (2)	0.0677 (12)
H9	−0.2647	0.8371	0.3719	0.081*
C10	−0.1146 (6)	0.7286 (2)	0.39979 (19)	0.0484 (10)
C11	−0.2626 (7)	0.7085 (3)	0.4547 (2)	0.0574 (11)
H11	−0.3817	0.7432	0.4643	0.069*
C12	−0.2334 (7)	0.6394 (2)	0.4938 (2)	0.0594 (11)
H12	−0.3333	0.6264	0.5296	0.071*
C13	−0.0538 (6)	0.5874 (2)	0.48056 (19)	0.0507 (10)
H13	−0.0362	0.5403	0.5083	0.061*
C14	0.0986 (6)	0.60337 (19)	0.42771 (17)	0.0389 (8)
C15	0.0688 (6)	0.67558 (19)	0.38365 (17)	0.0394 (8)
C16	0.3391 (6)	0.4827 (2)	0.46264 (18)	0.0519 (10)
H16B	0.2712	0.4920	0.5086	0.062*
H16A	0.4982	0.4833	0.4695	0.062*
C17	0.2717 (6)	0.3962 (2)	0.43668 (18)	0.0463 (9)
C18	0.3875 (8)	0.3775 (3)	0.3663 (2)	0.0758 (13)
H18B	0.3323	0.4139	0.3303	0.114*
H18A	0.3588	0.3213	0.3529	0.114*
H18C	0.5440	0.3855	0.3716	0.114*
C19	0.3484 (8)	0.3340 (2)	0.4927 (2)	0.0747 (14)
H19A	0.3080	0.2793	0.4781	0.112*
H19C	0.2791	0.3464	0.5372	0.112*
H19B	0.5062	0.3373	0.4978	0.112*
C20	0.0236 (7)	0.3885 (2)	0.4256 (2)	0.0684 (12)
H20C	−0.0510	0.3955	0.4701	0.103*
H20A	−0.0099	0.3350	0.4066	0.103*
H20B	−0.0252	0.4303	0.3930	0.103*

	U11	U22	U33	U12	U13	U23
N1	0.082 (3)	0.059 (2)	0.067 (2)	0.013 (2)	0.035 (2)	0.0214 (17)
N2	0.049 (2)	0.0449 (19)	0.060 (2)	0.0077 (17)	0.0144 (18)	0.0112 (15)
C1	0.057 (3)	0.087 (3)	0.074 (3)	−0.001 (3)	−0.001 (3)	−0.017 (2)
C2	0.102 (4)	0.118 (4)	0.084 (3)	0.004 (4)	0.043 (4)	0.008 (3)
C3	0.093 (4)	0.105 (4)	0.074 (3)	−0.028 (3)	−0.018 (3)	−0.010 (3)
C4	0.053 (2)	0.064 (3)	0.046 (2)	−0.007 (2)	0.009 (2)	−0.0063 (18)
C5	0.081 (3)	0.074 (3)	0.062 (3)	−0.001 (3)	0.020 (3)	0.011 (2)
C6	0.051 (2)	0.041 (2)	0.048 (2)	0.0028 (19)	−0.0014 (19)	0.0013 (17)
C7	0.076 (3)	0.053 (3)	0.066 (3)	−0.001 (2)	0.006 (2)	0.012 (2)
C8	0.098 (4)	0.052 (3)	0.079 (3)	0.018 (3)	−0.006 (3)	0.016 (2)
C9	0.073 (3)	0.049 (3)	0.081 (3)	0.018 (2)	−0.014 (3)	−0.005 (2)
C10	0.048 (2)	0.041 (2)	0.056 (2)	0.0026 (19)	−0.011 (2)	−0.0122 (17)
C11	0.042 (2)	0.061 (3)	0.070 (3)	0.009 (2)	0.004 (2)	−0.021 (2)
C12	0.055 (3)	0.056 (3)	0.067 (3)	−0.006 (2)	0.020 (2)	−0.017 (2)
C13	0.062 (3)	0.041 (2)	0.049 (2)	−0.001 (2)	0.009 (2)	0.0002 (17)
C14	0.046 (2)	0.0346 (19)	0.0361 (18)	−0.0018 (17)	0.0020 (18)	−0.0066 (15)
C15	0.043 (2)	0.0343 (18)	0.0413 (19)	−0.0026 (17)	−0.0055 (18)	−0.0056 (15)
C16	0.048 (2)	0.047 (2)	0.061 (2)	−0.0022 (19)	−0.001 (2)	0.0096 (18)
C17	0.043 (2)	0.043 (2)	0.053 (2)	−0.0013 (18)	−0.0042 (19)	0.0048 (17)
C18	0.079 (3)	0.065 (3)	0.083 (3)	0.000 (3)	0.013 (3)	−0.005 (2)
C19	0.071 (3)	0.056 (3)	0.097 (3)	0.002 (2)	−0.019 (3)	0.026 (2)
C20	0.054 (3)	0.060 (3)	0.091 (3)	−0.004 (2)	−0.011 (2)	0.004 (2)

N1—C6	1.391 (5)	C9—C10	1.418 (5)
N1—C5	1.453 (5)	C9—H9	0.9300
N1—H1	0.86 (3)	C10—C11	1.407 (5)
N2—C14	1.398 (4)	C10—C15	1.434 (5)
N2—C16	1.463 (4)	C11—C12	1.352 (5)
N2—H2	0.86 (3)	C11—H11	0.9300
C1—C4	1.528 (5)	C12—C13	1.396 (5)
C1—H1C	0.9600	C12—H12	0.9300
C1—H1A	0.9600	C13—C14	1.382 (5)
C1—H1B	0.9600	C13—H13	0.9300
C2—C4	1.533 (5)	C14—C15	1.446 (4)
C2—H2C	0.9600	C16—C17	1.537 (5)
C2—H2B	0.9600	C16—H16B	0.9700
C2—H2A	0.9600	C16—H16A	0.9700
C3—C4	1.526 (6)	C17—C20	1.519 (5)
C3—H3A	0.9600	C17—C18	1.531 (5)
C3—H3C	0.9600	C17—C19	1.532 (5)
C3—H3B	0.9600	C18—H18B	0.9600
C4—C5	1.521 (6)	C18—H18A	0.9600
C5—H5B	0.9700	C18—H18C	0.9600
C5—H5A	0.9700	C19—H19A	0.9600
C6—C7	1.390 (5)	C19—H19C	0.9600
C6—C15	1.438 (5)	C19—H19B	0.9600
C7—C8	1.396 (6)	C20—H20C	0.9600
C7—H7	0.9300	C20—H20A	0.9600
C8—C9	1.349 (6)	C20—H20B	0.9600
C8—H8	0.9300
C6—N1—C5	121.7 (3)	C11—C10—C9	119.3 (4)
C6—N1—H1	107 (5)	C11—C10—C15	120.6 (3)
C5—N1—H1	108 (4)	C9—C10—C15	120.1 (4)
C14—N2—C16	123.7 (3)	C12—C11—C10	120.6 (4)
C14—N2—H2	112 (3)	C12—C11—H11	119.7
C16—N2—H2	110.6 (14)	C10—C11—H11	119.7
C4—C1—H1C	109.5	C11—C12—C13	120.3 (4)
C4—C1—H1A	109.5	C11—C12—H12	119.9
H1C—C1—H1A	109.5	C13—C12—H12	119.9
C4—C1—H1B	109.5	C14—C13—C12	122.3 (3)
H1C—C1—H1B	109.5	C14—C13—H13	118.9
H1A—C1—H1B	109.5	C12—C13—H13	118.9
C4—C2—H2C	109.5	C13—C14—N2	121.5 (3)
C4—C2—H2B	109.5	C13—C14—C15	118.9 (3)
H2C—C2—H2B	109.5	N2—C14—C15	119.6 (3)
C4—C2—H2A	109.5	C10—C15—C6	117.6 (3)
H2C—C2—H2A	109.5	C10—C15—C14	117.3 (3)
H2B—C2—H2A	109.5	C6—C15—C14	125.1 (3)
C4—C3—H3A	109.5	N2—C16—C17	115.9 (3)
C4—C3—H3C	109.5	N2—C16—H16B	108.3
H3A—C3—H3C	109.5	C17—C16—H16B	108.3
C4—C3—H3B	109.5	N2—C16—H16A	108.3
H3A—C3—H3B	109.5	C17—C16—H16A	108.3
H3C—C3—H3B	109.5	H16B—C16—H16A	107.4
C5—C4—C3	111.0 (4)	C20—C17—C18	108.4 (4)
C5—C4—C1	111.5 (3)	C20—C17—C19	109.9 (3)
C3—C4—C1	109.4 (4)	C18—C17—C19	109.2 (3)
C5—C4—C2	107.0 (3)	C20—C17—C16	112.3 (3)
C3—C4—C2	108.4 (3)	C18—C17—C16	109.6 (3)
C1—C4—C2	109.5 (4)	C19—C17—C16	107.4 (3)
N1—C5—C4	113.2 (3)	C17—C18—H18B	109.5
N1—C5—H5B	108.9	C17—C18—H18A	109.5
C4—C5—H5B	108.9	H18B—C18—H18A	109.5
N1—C5—H5A	108.9	C17—C18—H18C	109.5
C4—C5—H5A	108.9	H18B—C18—H18C	109.5
H5B—C5—H5A	107.8	H18A—C18—H18C	109.5
C7—C6—N1	120.3 (4)	C17—C19—H19A	109.5
C7—C6—C15	119.4 (4)	C17—C19—H19C	109.5
N1—C6—C15	120.3 (3)	H19A—C19—H19C	109.5
C6—C7—C8	121.0 (4)	C17—C19—H19B	109.5
C6—C7—H7	119.5	H19A—C19—H19B	109.5
C8—C7—H7	119.5	H19C—C19—H19B	109.5
C9—C8—C7	121.4 (4)	C17—C20—H20C	109.5
C9—C8—H8	119.3	C17—C20—H20A	109.5
C7—C8—H8	119.3	H20C—C20—H20A	109.5
C8—C9—C10	120.2 (4)	C17—C20—H20B	109.5
C8—C9—H9	119.9	H20C—C20—H20B	109.5
C10—C9—H9	119.9	H20A—C20—H20B	109.5
C6—N1—C5—C4	−163.9 (4)	C16—N2—C14—C13	−7.4 (5)
C3—C4—C5—N1	69.2 (5)	C16—N2—C14—C15	172.6 (3)
C1—C4—C5—N1	−53.1 (5)	C11—C10—C15—C6	176.7 (3)
C2—C4—C5—N1	−172.7 (4)	C9—C10—C15—C6	−4.4 (5)
C5—N1—C6—C7	−7.5 (6)	C11—C10—C15—C14	−2.3 (5)
C5—N1—C6—C15	170.6 (4)	C9—C10—C15—C14	176.6 (3)
N1—C6—C7—C8	173.9 (4)	C7—C6—C15—C10	6.2 (5)
C15—C6—C7—C8	−4.2 (6)	N1—C6—C15—C10	−171.9 (3)
C6—C7—C8—C9	0.1 (7)	C7—C6—C15—C14	−174.8 (3)
C7—C8—C9—C10	1.8 (7)	N1—C6—C15—C14	7.0 (5)
C8—C9—C10—C11	179.4 (4)	C13—C14—C15—C10	2.6 (4)
C8—C9—C10—C15	0.4 (6)	N2—C14—C15—C10	−177.4 (3)
C9—C10—C11—C12	−178.2 (4)	C13—C14—C15—C6	−176.4 (3)
C15—C10—C11—C12	0.7 (5)	N2—C14—C15—C6	3.7 (5)
C10—C11—C12—C13	0.8 (6)	C14—N2—C16—C17	101.3 (4)
C11—C12—C13—C14	−0.5 (6)	N2—C16—C17—C20	−59.1 (4)
C12—C13—C14—N2	178.7 (3)	N2—C16—C17—C18	61.5 (4)
C12—C13—C14—C15	−1.2 (5)	N2—C16—C17—C19	−180.0 (3)