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Acta Crystallographica Section E: Structure Reports Online logoLink to Acta Crystallographica Section E: Structure Reports Online
. 2010 Jan 30;66(Pt 2):o475. doi: 10.1107/S1600536810001881

N,N-Bis(2-pyridylmeth­yl)aniline

Jun-Tao Kang a, Guan-Hua Wang a, Jing-Wei Xu a,*, Wei Yang a,*
PMCID: PMC2979909  PMID: 21579884

Abstract

In the title compound, C18H17N3, 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 inter­molecular C—H⋯π inter­actions 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 ▶).graphic file with name e-66-0o475-scheme1.jpg

Experimental

Crystal data

  • C18H17N3

  • M r = 275.35

  • Monoclinic, Inline graphic

  • 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.

Supplementary Material

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

e-66-0o475-sup1.cif (16.2KB, cif)

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

e-66-0o475-Isup2.hkl (127.3KB, hkl)

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

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

Acknowledgments

This work is supported by the State Key Laboratory of Electroanalytical Chemistry, Changchun Institute of Applied Chemistry, Changchun, China.

supplementary crystallographic information

Comment

Bis(pyridin-2-ylmethyl)amine derivatives are often used as zinc probes (Royzen et al., 2006; Komatsu et al., 2007; Xiang & Tong, 2006). The title compound, N,N-bis(pyridin-2-ylmethyl)aniline, has been also used as a ligand in metal complexes (Nielsen et al., 2005, 2007; Bjernemose et al., 2003; Hazell et al., 2000; Ugozzoli et al., 2002). Herein, we report the molecular and crystal structure of this compound. The molecule has three rings trending to different orientations, of which the dihedral angle between the two pyridyl rings is 54.55 (13)°, and the dihedral angles between the phenyl ring and the two pyridyl rings are 73.61 (13) and 81.40 (13)°. Intermolecular C—H···π interactions exist in the crystal, which connect molecules into a two-dimensional layer structure.

Experimental

The title compound was synthesized according to previous reported literature (Foxon et al., 2007). Single crystals suitable for X-ray diffraction were obtained by slow evaporation of a solution of the title compound in acetone at room temperature.

Refinement

H atoms were placed geometrically with C—H distances of 0.93–0.97 Å and refined using a riding model, with Uiso(H) = 1.2Ueq(C).

Figures

Fig. 1.

Fig. 1.

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Molecular structure of the title compound. Displacement ellipsoids are drawn at the 30% probability level.

Crystal data

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
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Data collection

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
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Refinement

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
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Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

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*
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Atomic displacement parameters (Å2)

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)
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Geometric parameters (Å, °)

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)
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Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C8–C12/N2 and C1–C6 rings, respectively.
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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
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Symmetry codes: (i) −x+1, −y+1, −z+2; (ii) −x, −y+1, −z+2; (iii) x, y, z+1.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: IS2511).

References

  1. Bjernemose, J., Hazell, A., McKenzie, C. J., Mahon, M. F., Nielsen, L. P., Raithby, P. R., Simonsen, O., Toftlund, H. & Wolny, J. A. (2003). Polyhedron, 22, 875–885.
  2. Bruker (2007). SMART and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  3. Foxon, S., Xu, J.-Y., Turba, S., Leibold, M., Hampel, F., Heinemann, F. W., Walter, O. W., Ūrtele, C., Holthausen, M. & Schindler, S. (2007). Eur. J. Inorg. Chem.3, 429–443.
  4. Hazell, A., McKenzie, C. J. & Nielsen, L. P. (2000). Polyhedron, 19, 1333–1338.
  5. Komatsu, K., Urano, Y., Kojima, H. & Nagano, T. (2007). J. Am. Chem. Soc.129, 13447–13454. [DOI] [PubMed]
  6. Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst.39, 453–457.
  7. Nielsen, A., Bond, A. D. & McKenzie, C. J. (2005). Acta Cryst. E61, m478–m480.
  8. Nielsen, A., Veltze, S., Bond, A. D. & McKenzie, C. J. (2007). Polyhedron, 26, 1649–1657.
  9. Royzen, M., Durandin, A., Young, V. G., Geacintov, N. E. & Canary, J. W. (2006). J. Am. Chem. Soc.128, 3854–3855. [DOI] [PubMed]
  10. Sheldrick, G. M. (1996). SADABS University of Göttingen, Germany.
  11. Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [DOI] [PubMed]
  12. Ugozzoli, F., Massera, C., Lanfredi, A. M. M., Marsich, N. & Camus, A. (2002). Inorg. Chim. Acta, 340, 97–104.
  13. Xiang, Y. & Tong, A.-J. (2006). Org. Lett.8, 1549–1552. [DOI] [PubMed]

Associated Data

This section collects any data citations, data availability statements, or supplementary materials included in this article.

Supplementary Materials

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

e-66-0o475-sup1.cif (16.2KB, cif)

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

e-66-0o475-Isup2.hkl (127.3KB, hkl)

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

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography

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