N,N-Bis(2-pyridylmeth-yl)aniline.

In the title compound, C(18)H(17)N(3), the two pyridyl rings make a dihedral angle of 54.55 (13)°. The dihedral angles between the phenyl ring and the two pyridyl rings are 73.61 (13) and 81.40 (13)°. In the crystal, weak inter-molecular C-H⋯π inter-actions are observed.

Related literature

For bis­(pyridin-2-ylmeth­yl)amine derivatives, see: Komatsu et al. (2007 ▶); Royzen et al. (2006 ▶); Xiang & Tong (2006 ▶). For related structures, see: Nielsen et al. (2005 ▶, 2007 ▶); Bjernemose et al. (2003 ▶); Hazell et al. (2000 ▶); Ugozzoli et al. (2002 ▶). For the synthesis, see: Foxon et al. (2007 ▶).

Experimental

Crystal data

C18H17N3

M = 275.35

Monoclinic,

a = 11.4866 (19) Å

b = 16.811 (3) Å

c = 7.7930 (12) Å

β = 101.471 (3)°

V = 1474.8 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 293 K

0.26 × 0.17 × 0.12 mm

Data collection

Bruker SMART APEX CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.981, T max = 0.991

7541 measured reflections

2591 independent reflections

1251 reflections with I > 2σ(I)

R int = 0.057

Refinement

R[F 2 > 2σ(F 2)] = 0.049

wR(F 2) = 0.117

S = 0.93

2591 reflections

190 parameters

H-atom parameters constrained

Δρmax = 0.14 e Å−3

Δρmin = −0.14 e Å−3

Data collection: SMART (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: SHELXTL (Sheldrick, 2008 ▶) and Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810001881/is2511sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810001881/is2511Isup2.hkl

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

C18H17N3	F(000) = 584
Mr = 275.35	Dx = 1.240 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 649 reflections
a = 11.4866 (19) Å	θ = 2.4–19.7°
b = 16.811 (3) Å	µ = 0.08 mm−1
c = 7.7930 (12) Å	T = 293 K
β = 101.471 (3)°	Block, colorless
V = 1474.8 (4) Å3	0.26 × 0.17 × 0.12 mm
Z = 4

Bruker SMART APEX CCD diffractometer	2591 independent reflections
Radiation source: sealed tube	1251 reflections with I > 2σ(I)
graphite	Rint = 0.057
φ and ω scans	θmax = 25.1°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −10→13
Tmin = 0.981, Tmax = 0.991	k = −19→19
7541 measured reflections	l = −9→8

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)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.117	H-atom parameters constrained
S = 0.93	w = 1/[σ2(Fo2) + (0.0459P)2] where P = (Fo2 + 2Fc2)/3
2591 reflections	(Δ/σ)max < 0.001
190 parameters	Δρmax = 0.14 e Å−3
0 restraints	Δρmin = −0.14 e Å−3

	x	y	z	Uiso*/Ueq
N1	0.27837 (18)	0.47311 (12)	0.8924 (2)	0.0521 (6)
N2	0.2502 (2)	0.66652 (12)	0.6656 (3)	0.0633 (6)
N3	0.0590 (2)	0.36999 (13)	1.1010 (3)	0.0649 (6)
C1	0.3652 (2)	0.42824 (15)	0.8353 (3)	0.0472 (6)
C2	0.3695 (2)	0.34558 (15)	0.8561 (3)	0.0559 (7)
H2	0.3130	0.3204	0.9074	0.067*
C3	0.4559 (3)	0.30090 (16)	0.8019 (3)	0.0664 (8)
H3	0.4570	0.2461	0.8183	0.080*
C4	0.5403 (3)	0.33561 (18)	0.7243 (4)	0.0667 (8)
H4	0.5982	0.3049	0.6877	0.080*
C5	0.5375 (2)	0.41657 (18)	0.7018 (3)	0.0630 (8)
H5	0.5941	0.4409	0.6491	0.076*
C6	0.4515 (2)	0.46266 (16)	0.7564 (3)	0.0553 (7)
H6	0.4515	0.5175	0.7401	0.066*
C7	0.2770 (2)	0.55875 (14)	0.8723 (3)	0.0569 (7)
H7A	0.3572	0.5784	0.9120	0.068*
H7B	0.2283	0.5811	0.9487	0.068*
C8	0.2311 (2)	0.58934 (15)	0.6879 (3)	0.0469 (6)
C9	0.1736 (2)	0.54150 (14)	0.5561 (3)	0.0567 (7)
H9	0.1621	0.4878	0.5765	0.068*
C10	0.1332 (2)	0.57366 (17)	0.3930 (3)	0.0648 (8)
H10	0.0940	0.5420	0.3017	0.078*
C11	0.1510 (3)	0.65247 (19)	0.3663 (4)	0.0703 (9)
H11	0.1245	0.6758	0.2573	0.084*
C12	0.2089 (3)	0.69592 (16)	0.5048 (4)	0.0730 (9)
H12	0.2207	0.7498	0.4866	0.088*
C13	0.1675 (2)	0.43629 (15)	0.9124 (3)	0.0588 (7)
H13A	0.1477	0.3955	0.8233	0.071*
H13B	0.1055	0.4763	0.8889	0.071*
C14	0.1647 (2)	0.39913 (13)	1.0875 (3)	0.0470 (7)
C15	0.0517 (3)	0.33528 (16)	1.2541 (5)	0.0745 (9)
H15	−0.0216	0.3153	1.2668	0.089*
C16	0.1452 (3)	0.32745 (16)	1.3924 (4)	0.0713 (9)
H16	0.1360	0.3019	1.4946	0.086*
C17	0.2526 (3)	0.35824 (15)	1.3761 (4)	0.0631 (8)
H17	0.3177	0.3548	1.4683	0.076*
C18	0.2633 (2)	0.39451 (14)	1.2210 (3)	0.0538 (7)
H18	0.3357	0.4155	1.2067	0.065*

	U11	U22	U33	U12	U13	U23
N1	0.0523 (15)	0.0480 (13)	0.0571 (14)	0.0000 (12)	0.0131 (11)	0.0074 (10)
N2	0.0811 (18)	0.0502 (15)	0.0608 (16)	−0.0035 (12)	0.0198 (13)	0.0024 (11)
N3	0.0521 (16)	0.0707 (16)	0.0754 (18)	−0.0112 (13)	0.0209 (13)	−0.0024 (13)
C1	0.0477 (18)	0.0510 (17)	0.0402 (15)	−0.0018 (14)	0.0025 (12)	0.0056 (12)
C2	0.065 (2)	0.0538 (18)	0.0510 (17)	−0.0028 (15)	0.0166 (14)	0.0048 (13)
C3	0.078 (2)	0.0572 (18)	0.0641 (19)	0.0088 (17)	0.0151 (17)	0.0007 (15)
C4	0.062 (2)	0.075 (2)	0.064 (2)	0.0084 (17)	0.0129 (15)	−0.0038 (15)
C5	0.0474 (19)	0.081 (2)	0.0606 (19)	−0.0089 (17)	0.0098 (14)	0.0056 (16)
C6	0.0490 (17)	0.0583 (17)	0.0554 (17)	−0.0073 (15)	0.0027 (14)	0.0089 (13)
C7	0.067 (2)	0.0516 (17)	0.0518 (17)	0.0031 (14)	0.0115 (14)	0.0003 (12)
C8	0.0492 (17)	0.0454 (16)	0.0465 (16)	0.0047 (13)	0.0104 (12)	0.0013 (13)
C9	0.0641 (19)	0.0460 (15)	0.0554 (18)	0.0047 (14)	0.0007 (14)	0.0014 (14)
C10	0.060 (2)	0.072 (2)	0.0574 (19)	0.0117 (16)	−0.0015 (15)	−0.0101 (15)
C11	0.082 (2)	0.079 (2)	0.053 (2)	0.0183 (18)	0.0200 (17)	0.0141 (17)
C12	0.099 (3)	0.0552 (18)	0.072 (2)	0.0088 (18)	0.0345 (19)	0.0170 (17)
C13	0.0511 (18)	0.0672 (18)	0.0574 (18)	0.0035 (15)	0.0087 (13)	0.0072 (14)
C14	0.0452 (17)	0.0453 (15)	0.0528 (17)	−0.0010 (13)	0.0156 (14)	−0.0046 (12)
C15	0.070 (2)	0.071 (2)	0.094 (3)	−0.0126 (18)	0.043 (2)	−0.0042 (18)
C16	0.091 (3)	0.0649 (19)	0.067 (2)	0.004 (2)	0.037 (2)	0.0013 (16)
C17	0.067 (2)	0.0711 (19)	0.0524 (19)	0.0023 (17)	0.0146 (15)	−0.0002 (14)
C18	0.0471 (18)	0.0613 (18)	0.0550 (18)	−0.0075 (14)	0.0146 (15)	0.0003 (14)

N1—C1	1.393 (3)	C7—H7B	0.9700
N1—C7	1.448 (3)	C8—C9	1.367 (3)
N1—C13	1.452 (3)	C9—C10	1.374 (3)
N2—C8	1.333 (3)	C9—H9	0.9300
N2—C12	1.343 (3)	C10—C11	1.363 (3)
N3—C14	1.332 (3)	C10—H10	0.9300
N3—C15	1.346 (3)	C11—C12	1.362 (4)
C1—C6	1.392 (3)	C11—H11	0.9300
C1—C2	1.399 (3)	C12—H12	0.9300
C2—C3	1.376 (3)	C13—C14	1.507 (3)
C2—H2	0.9300	C13—H13A	0.9700
C3—C4	1.372 (4)	C13—H13B	0.9700
C3—H3	0.9300	C14—C18	1.379 (3)
C4—C5	1.372 (3)	C15—C16	1.368 (4)
C4—H4	0.9300	C15—H15	0.9300
C5—C6	1.388 (3)	C16—C17	1.367 (4)
C5—H5	0.9300	C16—H16	0.9300
C6—H6	0.9300	C17—C18	1.381 (3)
C7—C8	1.519 (3)	C17—H17	0.9300
C7—H7A	0.9700	C18—H18	0.9300
C1—N1—C7	119.8 (2)	C8—C9—H9	120.4
C1—N1—C13	120.2 (2)	C10—C9—H9	120.4
C7—N1—C13	116.4 (2)	C11—C10—C9	119.3 (2)
C8—N2—C12	116.3 (2)	C11—C10—H10	120.3
C14—N3—C15	116.6 (2)	C9—C10—H10	120.3
C6—C1—N1	122.3 (2)	C12—C11—C10	117.7 (3)
C6—C1—C2	116.9 (3)	C12—C11—H11	121.1
N1—C1—C2	120.8 (2)	C10—C11—H11	121.1
C3—C2—C1	121.2 (3)	N2—C12—C11	124.6 (3)
C3—C2—H2	119.4	N2—C12—H12	117.7
C1—C2—H2	119.4	C11—C12—H12	117.7
C4—C3—C2	121.3 (3)	N1—C13—C14	116.8 (2)
C4—C3—H3	119.4	N1—C13—H13A	108.1
C2—C3—H3	119.4	C14—C13—H13A	108.1
C3—C4—C5	118.5 (3)	N1—C13—H13B	108.1
C3—C4—H4	120.7	C14—C13—H13B	108.1
C5—C4—H4	120.7	H13A—C13—H13B	107.3
C4—C5—C6	121.0 (3)	N3—C14—C18	123.0 (2)
C4—C5—H5	119.5	N3—C14—C13	114.1 (2)
C6—C5—H5	119.5	C18—C14—C13	122.9 (2)
C5—C6—C1	121.1 (3)	N3—C15—C16	124.2 (3)
C5—C6—H6	119.5	N3—C15—H15	117.9
C1—C6—H6	119.5	C16—C15—H15	117.9
N1—C7—C8	115.68 (19)	C17—C16—C15	118.2 (3)
N1—C7—H7A	108.4	C17—C16—H16	120.9
C8—C7—H7A	108.4	C15—C16—H16	120.9
N1—C7—H7B	108.4	C16—C17—C18	119.2 (3)
C8—C7—H7B	108.4	C16—C17—H17	120.4
H7A—C7—H7B	107.4	C18—C17—H17	120.4
N2—C8—C9	122.8 (2)	C14—C18—C17	118.8 (3)
N2—C8—C7	114.7 (2)	C14—C18—H18	120.6
C9—C8—C7	122.5 (2)	C17—C18—H18	120.6
C8—C9—C10	119.2 (2)

Cg1 and Cg2 are the centroids of the C8–C12/N2 and C1–C6 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7A···Cg2i	0.97	2.98 (4)	3.825 (3)	146
C15—H15···Cg1ii	0.93	2.96 (3)	3.619 (4)	129
C17—H17···Cg2iii	0.93	2.65 (3)	3.530 (3)	159

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C8–C12/N2 and C1–C6 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C7—H7A⋯Cg2i	0.97	2.98 (4)	3.825 (3)	146
C15—H15⋯Cg1ii	0.93	2.96 (3)	3.619 (4)	129
C17—H17⋯Cg2iii	0.93	2.65 (3)	3.530 (3)	159

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