N,N-Bis(2-pyridylmeth-yl)-tert-butyl-amine.

In the title compound, C(16)H(21)N(3), the dihedral angle between the two pyridine rings is 88.11 (9)°. In the crystal, mol-ecules are linked through inter-molecular C-H⋯π inter-actions, forming a layer expanding parallel to the (10) plane.

Related literature

For related compounds, see: Mambanda et al. (2007 ▶); Foxon et al. (2007 ▶); Fujihara et al. (2004 ▶); Munro & Camp (2003 ▶). For metal complexes with the title compound as a ligand, see: Fujii et al. (2003 ▶); Lee & Lippard (2002 ▶); Mok et al. (1997 ▶). For the metal complex with N,N-bis­(2-pyridylmeth­yl)ethyl­amine as a ligand, see: Pal et al. (1992 ▶).

Experimental

Crystal data

C16H21N3

M = 255.36

Monoclinic,

a = 6.1808 (3) Å

b = 17.9502 (8) Å

c = 13.7079 (6) Å

β = 100.239 (4)°

V = 1496.62 (12) Å3

Z = 4

Mo Kα radiation

μ = 0.07 mm−1

T = 293 (2) K

0.50 × 0.50 × 0.30 mm

Data collection

Oxford Diffraction Xcalibur2 CCD diffractometer

Absorption correction: multi-scan (; Oxford Diffraction, 2008 ▶) T min = 0.967, T max = 0.980

7475 measured reflections

2392 independent reflections

2024 reflections with I > 2σ(I)

R int = 0.012

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.119

S = 1.02

2392 reflections

175 parameters

2 restraints

H-atom parameters constrained

Δρmax = 0.21 e Å−3

Δρmin = −0.22 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2008 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2008 ▶); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809001366/is2355sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809001366/is2355Isup2.hkl

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

C16H21N3	F(000) = 552
Mr = 255.36	Dx = 1.133 Mg m−3
Monoclinic, Cc	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C -2yc	Cell parameters from 4672 reflections
a = 6.1808 (3) Å	θ = 3.9–32.0°
b = 17.9502 (8) Å	µ = 0.07 mm−1
c = 13.7079 (6) Å	T = 293 K
β = 100.239 (4)°	Plate, colourless
V = 1496.62 (12) Å3	0.50 × 0.50 × 0.30 mm
Z = 4

Oxford Diffraction Xcalibur2 CCD diffractometer	2392 independent reflections
Radiation source: Enhance (Mo)X-Ray Source	2024 reflections with I > 2σ(I)
graphite	Rint = 0.012
Detector resolution: 8.4190 pixels mm-1	θmax = 31.9°, θmin = 4.1°
ω–2θ scans	h = −8→7
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2008)	k = −26→26
Tmin = 0.967, Tmax = 0.980	l = −18→20
7475 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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.119	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.0873P)2 + 0.017P] where P = (Fo2 + 2Fc2)/3
2392 reflections	(Δ/σ)max = 0.001
175 parameters	Δρmax = 0.21 e Å−3
2 restraints	Δρmin = −0.21 e Å−3
0 constraints

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
C14	0.2251 (5)	0.16330 (11)	0.59751 (18)	0.0645 (6)
H20	0.1452	0.1875	0.6425	0.097*
H21	0.2314	0.1955	0.5421	0.097*
H19	0.3716	0.1525	0.6311	0.097*
C15	0.2342 (5)	0.05704 (14)	0.48509 (17)	0.0679 (6)
H18	0.3767	0.0409	0.5180	0.102*
H16	0.2508	0.0937	0.4359	0.102*
H17	0.1537	0.0152	0.4537	0.102*
C16	−0.1269 (5)	0.10773 (16)	0.5103 (2)	0.0739 (7)
H15	−0.1940	0.0630	0.4806	0.111*
H14	−0.1260	0.1449	0.4600	0.111*
H13	−0.2090	0.1258	0.5586	0.111*
N3	0.1632 (2)	0.14031 (8)	0.88126 (11)	0.0448 (3)
C9	0.2329 (2)	0.09809 (8)	0.81277 (11)	0.0365 (3)
N1	0.1221 (2)	0.03781 (7)	0.64559 (9)	0.0382 (3)
C3	0.1172 (3)	−0.09657 (8)	0.68278 (12)	0.0384 (3)
C10	0.4530 (3)	0.08012 (10)	0.81845 (13)	0.0434 (3)
H8	0.4982	0.0513	0.7694	0.052*
C1	0.1094 (3)	0.09104 (10)	0.56073 (13)	0.0455 (4)
C2	0.0134 (3)	−0.03384 (10)	0.61861 (13)	0.0452 (4)
H11	0.0200	−0.0449	0.5499	0.054*
H12	−0.1403	−0.0300	0.6245	0.054*
N2	−0.0196 (2)	−0.14516 (8)	0.71406 (13)	0.0476 (3)
C8	0.0527 (3)	0.06774 (11)	0.73393 (12)	0.0442 (4)
H9	−0.0232	0.0287	0.7633	0.053*
H10	−0.0527	0.1073	0.7137	0.053*
C12	0.5344 (3)	0.14791 (10)	0.96934 (14)	0.0529 (4)
H6	0.6329	0.1652	1.0240	0.063*
C11	0.6047 (3)	0.10564 (11)	0.89812 (15)	0.0501 (4)
H7	0.7530	0.0941	0.9031	0.060*
C4	0.3437 (3)	−0.10609 (10)	0.70322 (14)	0.0466 (4)
H4	0.4352	−0.0713	0.6809	0.056*
C13	0.3140 (4)	0.16421 (10)	0.95790 (14)	0.0519 (4)
H5	0.2664	0.1935	1.0060	0.062*
C5	0.4322 (3)	−0.16716 (12)	0.75666 (16)	0.0553 (5)
H3	0.5836	−0.1743	0.7708	0.066*
C6	0.2920 (4)	−0.21757 (11)	0.78883 (17)	0.0567 (5)
H2	0.3460	−0.2594	0.8252	0.068*
C7	0.0701 (3)	−0.20409 (10)	0.76555 (17)	0.0554 (5)
H1	−0.0242	−0.2383	0.7871	0.066*

	U11	U22	U33	U12	U13	U23
C14	0.0927 (17)	0.0403 (9)	0.0584 (12)	−0.0074 (10)	0.0077 (11)	0.0060 (8)
C15	0.0990 (18)	0.0620 (12)	0.0486 (11)	−0.0019 (12)	0.0296 (11)	0.0014 (9)
C16	0.0720 (14)	0.0773 (16)	0.0638 (13)	0.0155 (12)	−0.0114 (11)	0.0176 (11)
N3	0.0476 (8)	0.0460 (7)	0.0408 (7)	0.0030 (6)	0.0075 (6)	−0.0021 (5)
C9	0.0370 (7)	0.0395 (7)	0.0324 (6)	−0.0014 (5)	0.0047 (5)	0.0033 (5)
N1	0.0426 (7)	0.0397 (6)	0.0307 (6)	−0.0034 (5)	0.0021 (5)	0.0008 (4)
C3	0.0404 (8)	0.0389 (7)	0.0347 (7)	−0.0029 (6)	0.0033 (5)	−0.0005 (5)
C10	0.0369 (7)	0.0529 (9)	0.0396 (7)	0.0002 (6)	0.0044 (6)	−0.0019 (6)
C1	0.0559 (10)	0.0416 (8)	0.0371 (7)	0.0006 (6)	0.0034 (7)	0.0054 (6)
C2	0.0446 (8)	0.0451 (8)	0.0409 (8)	−0.0067 (6)	−0.0060 (6)	0.0039 (6)
N2	0.0412 (7)	0.0437 (7)	0.0568 (9)	−0.0058 (6)	0.0056 (6)	0.0045 (6)
C8	0.0342 (7)	0.0603 (10)	0.0369 (7)	−0.0018 (6)	0.0031 (6)	−0.0030 (6)
C12	0.0612 (11)	0.0493 (9)	0.0427 (9)	−0.0136 (8)	−0.0054 (8)	0.0022 (7)
C11	0.0403 (8)	0.0573 (10)	0.0493 (9)	−0.0036 (7)	−0.0013 (7)	0.0072 (7)
C4	0.0371 (8)	0.0526 (9)	0.0514 (9)	−0.0026 (6)	0.0114 (7)	0.0003 (7)
C13	0.0678 (11)	0.0456 (8)	0.0413 (9)	−0.0018 (8)	0.0071 (8)	−0.0066 (7)
C5	0.0433 (9)	0.0576 (10)	0.0637 (12)	0.0114 (8)	0.0061 (8)	−0.0027 (9)
C6	0.0618 (11)	0.0419 (8)	0.0640 (11)	0.0110 (7)	0.0043 (9)	0.0033 (8)
C7	0.0539 (10)	0.0426 (9)	0.0702 (12)	−0.0057 (7)	0.0127 (9)	0.0088 (8)

C14—C1	1.523 (3)	C3—C2	1.501 (2)
C14—H20	0.9600	C10—C11	1.385 (2)
C14—H21	0.9600	C10—H8	0.9300
C14—H19	0.9600	C2—H11	0.9700
C15—C1	1.525 (3)	C2—H12	0.9700
C15—H18	0.9600	N2—C7	1.336 (2)
C15—H16	0.9600	C8—H9	0.9700
C15—H17	0.9600	C8—H10	0.9700
C16—C1	1.531 (3)	C12—C11	1.367 (3)
C16—H15	0.9600	C12—C13	1.375 (3)
C16—H14	0.9600	C12—H6	0.9300
C16—H13	0.9600	C11—H7	0.9300
N3—C9	1.336 (2)	C4—C5	1.377 (3)
N3—C13	1.345 (2)	C4—H4	0.9300
C9—C10	1.387 (2)	C13—H5	0.9300
C9—C8	1.509 (2)	C5—C6	1.378 (3)
N1—C8	1.457 (2)	C5—H3	0.9300
N1—C2	1.468 (2)	C6—C7	1.374 (3)
N1—C1	1.497 (2)	C6—H2	0.9300
C3—N2	1.338 (2)	C7—H1	0.9300
C3—C4	1.388 (2)
C1—C14—H20	109.5	C15—C1—C16	109.18 (19)
C1—C14—H21	109.5	N1—C2—C3	112.38 (12)
H20—C14—H21	109.5	N1—C2—H11	109.1
C1—C14—H19	109.5	C3—C2—H11	109.1
H20—C14—H19	109.5	N1—C2—H12	109.1
H21—C14—H19	109.5	C3—C2—H12	109.1
C1—C15—H18	109.5	H11—C2—H12	107.9
C1—C15—H16	109.5	C7—N2—C3	117.31 (16)
H18—C15—H16	109.5	N1—C8—C9	116.05 (14)
C1—C15—H17	109.5	N1—C8—H9	108.3
H18—C15—H17	109.5	C9—C8—H9	108.3
H16—C15—H17	109.5	N1—C8—H10	108.3
C1—C16—H15	109.5	C9—C8—H10	108.3
C1—C16—H14	109.5	H9—C8—H10	107.4
H15—C16—H14	109.5	C11—C12—C13	118.10 (17)
C1—C16—H13	109.5	C11—C12—H6	121.0
H15—C16—H13	109.5	C13—C12—H6	121.0
H14—C16—H13	109.5	C12—C11—C10	119.36 (17)
C9—N3—C13	117.70 (16)	C12—C11—H7	120.3
N3—C9—C10	121.88 (15)	C10—C11—H7	120.3
N3—C9—C8	114.75 (14)	C5—C4—C3	119.78 (16)
C10—C9—C8	123.24 (14)	C5—C4—H4	120.1
C8—N1—C2	110.06 (14)	C3—C4—H4	120.1
C8—N1—C1	115.35 (14)	N3—C13—C12	123.79 (17)
C2—N1—C1	113.90 (12)	N3—C13—H5	118.1
N2—C3—C4	121.83 (15)	C12—C13—H5	118.1
N2—C3—C2	116.63 (15)	C4—C5—C6	118.68 (17)
C4—C3—C2	121.42 (15)	C4—C5—H3	120.7
C11—C10—C9	119.16 (17)	C6—C5—H3	120.7
C11—C10—H8	120.4	C7—C6—C5	117.95 (18)
C9—C10—H8	120.4	C7—C6—H2	121.0
N1—C1—C14	109.25 (14)	C5—C6—H2	121.0
N1—C1—C15	108.06 (15)	N2—C7—C6	124.45 (18)
C14—C1—C15	107.53 (19)	N2—C7—H1	117.8
N1—C1—C16	112.96 (17)	C6—C7—H1	117.8
C14—C1—C16	109.70 (18)
C13—N3—C9—C10	−1.1 (2)	C2—C3—N2—C7	175.54 (17)
C13—N3—C9—C8	174.86 (16)	C2—N1—C8—C9	134.62 (15)
N3—C9—C10—C11	1.0 (2)	C1—N1—C8—C9	−94.82 (18)
C8—C9—C10—C11	−174.62 (17)	N3—C9—C8—N1	165.09 (14)
C8—N1—C1—C14	50.8 (2)	C10—C9—C8—N1	−19.0 (2)
C2—N1—C1—C14	179.45 (17)	C13—C12—C11—C10	−0.8 (3)
C8—N1—C1—C15	167.47 (17)	C9—C10—C11—C12	0.0 (3)
C2—N1—C1—C15	−63.8 (2)	N2—C3—C4—C5	0.3 (3)
C8—N1—C1—C16	−71.6 (2)	C2—C3—C4—C5	−175.51 (17)
C2—N1—C1—C16	57.1 (2)	C9—N3—C13—C12	0.3 (3)
C8—N1—C2—C3	−77.86 (18)	C11—C12—C13—N3	0.7 (3)
C1—N1—C2—C3	150.82 (15)	C3—C4—C5—C6	−0.1 (3)
N2—C3—C2—N1	137.29 (16)	C4—C5—C6—C7	0.1 (3)
C4—C3—C2—N1	−46.7 (2)	C3—N2—C7—C6	0.5 (3)
C4—C3—N2—C7	−0.5 (3)	C5—C6—C7—N2	−0.3 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C7—H1···Cg2i	0.93	2.97	3.819 (2)	153
C15—H16···Cg1ii	0.96	2.94	3.836 (2)	156

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the N2/C3–C7and N3/C9–C13 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C7—H1⋯Cg2i	0.93	2.97	3.819 (2)	153
C15—H16⋯Cg1ii	0.96	2.94	3.836 (2)	156

Symmetry codes: (i) ; (ii) .