PMCCPMCCPMCC

Search tips
Search criteria 

Advanced

 
Logo of actaeInternational Union of Crystallographysearchopen accessarticle submissionjournal home pagethis article
 
Acta Crystallogr Sect E Struct Rep Online. 2010 February 1; 66(Pt 2): o475.
Published online 2010 January 30. doi:  10.1107/S1600536810001881
PMCID: PMC2979909

N,N-Bis(2-pyridylmeth­yl)aniline

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 [triangle]); Royzen et al. (2006 [triangle]); Xiang & Tong (2006 [triangle]). For related structures, see: Nielsen et al. (2005 [triangle], 2007 [triangle]); Bjernemose et al. (2003 [triangle]); Hazell et al. (2000 [triangle]); Ugozzoli et al. (2002 [triangle]). For the synthesis, see: Foxon et al. (2007 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-0o475-scheme1.jpg

Experimental

Crystal data

  • C18H17N3
  • M r = 275.35
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-0o475-efi1.jpg
  • 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 [triangle]) 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 [triangle]); cell refinement: SAINT (Bruker, 2007 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]) and Mercury (Macrae et al., 2006 [triangle]); software used to prepare material for publication: SHELXTL.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

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

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

Crystal data

C18H17N3F(000) = 584
Mr = 275.35Dx = 1.240 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 649 reflections
a = 11.4866 (19) Åθ = 2.4–19.7°
b = 16.811 (3) ŵ = 0.08 mm1
c = 7.7930 (12) ÅT = 293 K
β = 101.471 (3)°Block, colorless
V = 1474.8 (4) Å30.26 × 0.17 × 0.12 mm
Z = 4

Data collection

Bruker SMART APEX CCD diffractometer2591 independent reflections
Radiation source: sealed tube1251 reflections with I > 2σ(I)
graphiteRint = 0.057
[var phi] and ω scansθmax = 25.1°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −10→13
Tmin = 0.981, Tmax = 0.991k = −19→19
7541 measured reflectionsl = −9→8

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.049Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.117H-atom parameters constrained
S = 0.93w = 1/[σ2(Fo2) + (0.0459P)2] where P = (Fo2 + 2Fc2)/3
2591 reflections(Δ/σ)max < 0.001
190 parametersΔρmax = 0.14 e Å3
0 restraintsΔρmin = −0.14 e Å3

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

xyzUiso*/Ueq
N10.27837 (18)0.47311 (12)0.8924 (2)0.0521 (6)
N20.2502 (2)0.66652 (12)0.6656 (3)0.0633 (6)
N30.0590 (2)0.36999 (13)1.1010 (3)0.0649 (6)
C10.3652 (2)0.42824 (15)0.8353 (3)0.0472 (6)
C20.3695 (2)0.34558 (15)0.8561 (3)0.0559 (7)
H20.31300.32040.90740.067*
C30.4559 (3)0.30090 (16)0.8019 (3)0.0664 (8)
H30.45700.24610.81830.080*
C40.5403 (3)0.33561 (18)0.7243 (4)0.0667 (8)
H40.59820.30490.68770.080*
C50.5375 (2)0.41657 (18)0.7018 (3)0.0630 (8)
H50.59410.44090.64910.076*
C60.4515 (2)0.46266 (16)0.7564 (3)0.0553 (7)
H60.45150.51750.74010.066*
C70.2770 (2)0.55875 (14)0.8723 (3)0.0569 (7)
H7A0.35720.57840.91200.068*
H7B0.22830.58110.94870.068*
C80.2311 (2)0.58934 (15)0.6879 (3)0.0469 (6)
C90.1736 (2)0.54150 (14)0.5561 (3)0.0567 (7)
H90.16210.48780.57650.068*
C100.1332 (2)0.57366 (17)0.3930 (3)0.0648 (8)
H100.09400.54200.30170.078*
C110.1510 (3)0.65247 (19)0.3663 (4)0.0703 (9)
H110.12450.67580.25730.084*
C120.2089 (3)0.69592 (16)0.5048 (4)0.0730 (9)
H120.22070.74980.48660.088*
C130.1675 (2)0.43629 (15)0.9124 (3)0.0588 (7)
H13A0.14770.39550.82330.071*
H13B0.10550.47630.88890.071*
C140.1647 (2)0.39913 (13)1.0875 (3)0.0470 (7)
C150.0517 (3)0.33528 (16)1.2541 (5)0.0745 (9)
H15−0.02160.31531.26680.089*
C160.1452 (3)0.32745 (16)1.3924 (4)0.0713 (9)
H160.13600.30191.49460.086*
C170.2526 (3)0.35824 (15)1.3761 (4)0.0631 (8)
H170.31770.35481.46830.076*
C180.2633 (2)0.39451 (14)1.2210 (3)0.0538 (7)
H180.33570.41551.20670.065*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
N10.0523 (15)0.0480 (13)0.0571 (14)0.0000 (12)0.0131 (11)0.0074 (10)
N20.0811 (18)0.0502 (15)0.0608 (16)−0.0035 (12)0.0198 (13)0.0024 (11)
N30.0521 (16)0.0707 (16)0.0754 (18)−0.0112 (13)0.0209 (13)−0.0024 (13)
C10.0477 (18)0.0510 (17)0.0402 (15)−0.0018 (14)0.0025 (12)0.0056 (12)
C20.065 (2)0.0538 (18)0.0510 (17)−0.0028 (15)0.0166 (14)0.0048 (13)
C30.078 (2)0.0572 (18)0.0641 (19)0.0088 (17)0.0151 (17)0.0007 (15)
C40.062 (2)0.075 (2)0.064 (2)0.0084 (17)0.0129 (15)−0.0038 (15)
C50.0474 (19)0.081 (2)0.0606 (19)−0.0089 (17)0.0098 (14)0.0056 (16)
C60.0490 (17)0.0583 (17)0.0554 (17)−0.0073 (15)0.0027 (14)0.0089 (13)
C70.067 (2)0.0516 (17)0.0518 (17)0.0031 (14)0.0115 (14)0.0003 (12)
C80.0492 (17)0.0454 (16)0.0465 (16)0.0047 (13)0.0104 (12)0.0013 (13)
C90.0641 (19)0.0460 (15)0.0554 (18)0.0047 (14)0.0007 (14)0.0014 (14)
C100.060 (2)0.072 (2)0.0574 (19)0.0117 (16)−0.0015 (15)−0.0101 (15)
C110.082 (2)0.079 (2)0.053 (2)0.0183 (18)0.0200 (17)0.0141 (17)
C120.099 (3)0.0552 (18)0.072 (2)0.0088 (18)0.0345 (19)0.0170 (17)
C130.0511 (18)0.0672 (18)0.0574 (18)0.0035 (15)0.0087 (13)0.0072 (14)
C140.0452 (17)0.0453 (15)0.0528 (17)−0.0010 (13)0.0156 (14)−0.0046 (12)
C150.070 (2)0.071 (2)0.094 (3)−0.0126 (18)0.043 (2)−0.0042 (18)
C160.091 (3)0.0649 (19)0.067 (2)0.004 (2)0.037 (2)0.0013 (16)
C170.067 (2)0.0711 (19)0.0524 (19)0.0023 (17)0.0146 (15)−0.0002 (14)
C180.0471 (18)0.0613 (18)0.0550 (18)−0.0075 (14)0.0146 (15)0.0003 (14)

Geometric parameters (Å, °)

N1—C11.393 (3)C7—H7B0.9700
N1—C71.448 (3)C8—C91.367 (3)
N1—C131.452 (3)C9—C101.374 (3)
N2—C81.333 (3)C9—H90.9300
N2—C121.343 (3)C10—C111.363 (3)
N3—C141.332 (3)C10—H100.9300
N3—C151.346 (3)C11—C121.362 (4)
C1—C61.392 (3)C11—H110.9300
C1—C21.399 (3)C12—H120.9300
C2—C31.376 (3)C13—C141.507 (3)
C2—H20.9300C13—H13A0.9700
C3—C41.372 (4)C13—H13B0.9700
C3—H30.9300C14—C181.379 (3)
C4—C51.372 (3)C15—C161.368 (4)
C4—H40.9300C15—H150.9300
C5—C61.388 (3)C16—C171.367 (4)
C5—H50.9300C16—H160.9300
C6—H60.9300C17—C181.381 (3)
C7—C81.519 (3)C17—H170.9300
C7—H7A0.9700C18—H180.9300
C1—N1—C7119.8 (2)C8—C9—H9120.4
C1—N1—C13120.2 (2)C10—C9—H9120.4
C7—N1—C13116.4 (2)C11—C10—C9119.3 (2)
C8—N2—C12116.3 (2)C11—C10—H10120.3
C14—N3—C15116.6 (2)C9—C10—H10120.3
C6—C1—N1122.3 (2)C12—C11—C10117.7 (3)
C6—C1—C2116.9 (3)C12—C11—H11121.1
N1—C1—C2120.8 (2)C10—C11—H11121.1
C3—C2—C1121.2 (3)N2—C12—C11124.6 (3)
C3—C2—H2119.4N2—C12—H12117.7
C1—C2—H2119.4C11—C12—H12117.7
C4—C3—C2121.3 (3)N1—C13—C14116.8 (2)
C4—C3—H3119.4N1—C13—H13A108.1
C2—C3—H3119.4C14—C13—H13A108.1
C3—C4—C5118.5 (3)N1—C13—H13B108.1
C3—C4—H4120.7C14—C13—H13B108.1
C5—C4—H4120.7H13A—C13—H13B107.3
C4—C5—C6121.0 (3)N3—C14—C18123.0 (2)
C4—C5—H5119.5N3—C14—C13114.1 (2)
C6—C5—H5119.5C18—C14—C13122.9 (2)
C5—C6—C1121.1 (3)N3—C15—C16124.2 (3)
C5—C6—H6119.5N3—C15—H15117.9
C1—C6—H6119.5C16—C15—H15117.9
N1—C7—C8115.68 (19)C17—C16—C15118.2 (3)
N1—C7—H7A108.4C17—C16—H16120.9
C8—C7—H7A108.4C15—C16—H16120.9
N1—C7—H7B108.4C16—C17—C18119.2 (3)
C8—C7—H7B108.4C16—C17—H17120.4
H7A—C7—H7B107.4C18—C17—H17120.4
N2—C8—C9122.8 (2)C14—C18—C17118.8 (3)
N2—C8—C7114.7 (2)C14—C18—H18120.6
C9—C8—C7122.5 (2)C17—C18—H18120.6
C8—C9—C10119.2 (2)

Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C8–C12/N2 and C1–C6 rings, respectively.
D—H···AD—HH···AD···AD—H···A
C7—H7A···Cg2i0.972.98 (4)3.825 (3)146
C15—H15···Cg1ii0.932.96 (3)3.619 (4)129
C17—H17···Cg2iii0.932.65 (3)3.530 (3)159

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

  • 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.
  • Bruker (2007). SMART and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • 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.
  • Hazell, A., McKenzie, C. J. & Nielsen, L. P. (2000). Polyhedron, 19, 1333–1338.
  • Komatsu, K., Urano, Y., Kojima, H. & Nagano, T. (2007). J. Am. Chem. Soc.129, 13447–13454. [PubMed]
  • 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.
  • Nielsen, A., Bond, A. D. & McKenzie, C. J. (2005). Acta Cryst. E61, m478–m480.
  • Nielsen, A., Veltze, S., Bond, A. D. & McKenzie, C. J. (2007). Polyhedron, 26, 1649–1657.
  • Royzen, M., Durandin, A., Young, V. G., Geacintov, N. E. & Canary, J. W. (2006). J. Am. Chem. Soc.128, 3854–3855. [PubMed]
  • Sheldrick, G. M. (1996). SADABS University of Göttingen, Germany.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Ugozzoli, F., Massera, C., Lanfredi, A. M. M., Marsich, N. & Camus, A. (2002). Inorg. Chim. Acta, 340, 97–104.
  • Xiang, Y. & Tong, A.-J. (2006). Org. Lett.8, 1549–1552. [PubMed]

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