Comment

The asymmetric unit of the title compound, (I), contains one molecule. The two planar pyridyl rings are twisted (Fig. 1) about the central N atom, with an interplanar angle of 110.9°. The amine N atom is not involved in any hydrogen bonding but pyridyl atom N1 interacts with atom C3 in an adjacent ring (Table 1).

An edge-to-face interaction is found between the H atom on C2 and the plane of the pyridine ring containing atom N3 (Fig. 2). This H atom is 2.806 Å from the mean plane of the pyridine ring at (½ + x, ½ - y, ½ + z). The pyridine ring containing atom N3 is -stacked with its symmetry equivalent by inversion (symmetry code: 2 - x, -y, 1 - z). The interplanar and the centroid-to-centroid distances are 3.496 (2) and 3.971 Å respectively (Fig. 2).

Figure 1 Perspective view of (I), showing 50% probability displacement ellipsoids.

Figure 2 View showing the C-HN bond (C3 and N1), the interaction between the H atom bonded to C2 and the pyridyl ring, and the -stacking of the N3-containing pyridine rings [symmetry codes: (i) ½ + x, ½ - y, z - ½; (ii) 2 - x, -y, 1 - z; (iii) ½ + x, ½ - y, ½ + z.]

Experimental

2-(Aminomethyl)pyridine (4.95 g, 44.77 mmol) and pyridine-2-carboxaldehyde (4.96 g, 46.31 mmol) were dissolved in methanol (150 ml) (Lambert et al., 1997). The solution was stirred for 2 h at room temperature (yellow-orange solution). After slow addition of an excess of sodium borohydride, stirring was continued for 1 h (pale-yellow solution). The solvent was removed by rotary evaporation to give bis(pyridin-2-ylmethyl)amine (6.43 g, 73%) as an orange oil. Colourless crystals of the borane adduct appeared as a minor product after the oil was stored in a freezer overnight.

Crystal data

C12H15BN3 Mr = 213.09 Monoclinic, P21/n a = 5.3172 (4) Å b = 24.8494 (19) Å c = 9.3896 (7) Å = 102.938 (1)° V = 1209.14 (16) Å3 Z = 4 Dx = 1.171 Mg m-3 Mo K radiation Cell parameters from 3633 reflections = 2.4-27.5° = 0.07 mm-1 T = 150 (2) K Needle, colourless 0.55 × 0.17 × 0.09 mm

Data collection

Bruker SMART CCD area-detector diffractometer and scans Absorption correction: multi-scan (SADABS; Bruker, 1998) Tmin = 0.946, Tmax = 0.990 10293 measured reflections 2860 independent reflections 2156 reflections with I > 2(I) Rint = 0.023 max = 28.8° h = -7 6 k = -32 32 l = -12 12

Refinement

Refinement on F2 R[F2 > 2(F2)] = 0.043 wR(F2) = 0.116 S = 1.02 2860 reflections 148 parameters H atoms treated by a mixture of independent and constrained refinement w = 1/[2(Fo2) + (0.0526P)2 + 0.3966P] where P = (Fo2 + 2Fc2)/3 (/)max < 0.001 max = 0.25 e Å-3 min = -0.20 e Å-3

Table 1 Hydrogen-bonding geometry (Å, °) D-HA D-H HA DA D-HA C3-H3N1i 0.95 2.66 3.5215 (19) 150 Symmetry code: (i) .

H atoms bonded to C and B atoms were placed at calculated positions; the constrained C-H distances were 0.95, 0.98 and 0.99 Å for H atoms bonded to Csp², Bsp³ and methylene C atoms, respectively. They were refined using a riding model, with U_iso(H) = 1.2U_eq(B,C). The H atom bonded to the amine N atom was located in a difference map and the coordinates freely refined with a fixed U_iso value of 0.03 Å.

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2001); software used to prepare material for publication: SHELXTL.