N-Benzyl-pyridin-2-amine.

In the crystal of the title compound, C(12)H(12)N(2), inter-molecular N-H⋯N hydrogen bonds form rings of graph-set motif R(2) (2)(8) and C-H⋯π inter-actions further consolidate the dimers. Neighbouring dimers are further connected into a three-dimensional network by C-H⋯π inter-actions. The benzyl and pyridyl rings form a dihedral angle of 67.2 (1)°

Related literature

For general background to the topologies and potential applications of metal coordination polymers, see: Benelli & Gatteschi (2002 ▶). For related structures, see: Davies et al. (2001 ▶); Wan et al. (2004 ▶); Zhou & Richeson (1995 ▶). For bond-length data, see: Allen et al. (1987 ▶). For hydrogen-bonding graph-set motifs, see: Bernstein et al. (1995 ▶). For another report on the structure of N-benzyl­pyridin-2-amine, see: Wang & Zhao (2010 ▶).

Experimental

Crystal data

C12H12N2

M = 184.24

Triclinic,

a = 5.9014 (16) Å

b = 8.025 (2) Å

c = 10.561 (3) Å

α = 95.471 (4)°

β = 91.244 (4)°

γ = 94.779 (3)°

V = 495.9 (2) Å3

Z = 2

Mo Kα radiation

μ = 0.07 mm−1

T = 296 K

0.23 × 0.20 × 0.19 mm

Data collection

Bruker APEXII area-detector diffractometer

2551 measured reflections

1762 independent reflections

1387 reflections with I > 2σ(I)

R int = 0.012

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.115

S = 1.07

1762 reflections

127 parameters

H-atom parameters constrained

Δρmax = 0.23 e Å−3

Δρmin = −0.24 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); 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 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810044478/rz2510sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810044478/rz2510Isup2.hkl

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

C12H12N2	Z = 2
Mr = 184.24	F(000) = 196
Triclinic, P1	Dx = 1.234 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 5.9014 (16) Å	Cell parameters from 3415 reflections
b = 8.025 (2) Å	θ = 1.2–28.0°
c = 10.561 (3) Å	µ = 0.07 mm−1
α = 95.471 (4)°	T = 296 K
β = 91.244 (4)°	Block, colourless
γ = 94.779 (3)°	0.23 × 0.20 × 0.19 mm
V = 495.9 (2) Å3

Bruker APEXII area-detector diffractometer	1387 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.012
graphite	θmax = 25.3°, θmin = 1.9°
φ and ω scans	h = −6→7
2551 measured reflections	k = −9→9
1762 independent reflections	l = −9→12

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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.115	H-atom parameters constrained
S = 1.07	w = 1/[σ2(Fo2) + (0.0576P)2 + 0.0854P] where P = (Fo2 + 2Fc2)/3
1762 reflections	(Δ/σ)max < 0.001
127 parameters	Δρmax = 0.23 e Å−3
0 restraints	Δρmin = −0.24 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
C1	−0.1362 (3)	0.24905 (19)	0.36541 (15)	0.0350 (4)
H1	−0.2427	0.1909	0.4122	0.042*
C2	0.0725 (3)	0.30933 (18)	0.42172 (14)	0.0308 (4)
C3	0.2280 (3)	0.39773 (19)	0.34991 (15)	0.0357 (4)
H3	0.3689	0.4396	0.3860	0.043*
C4	0.1748 (3)	0.4236 (2)	0.22596 (16)	0.0397 (4)
H4	0.2798	0.4832	0.1793	0.048*
C5	−0.0331 (3)	0.3616 (2)	0.17061 (16)	0.0408 (4)
H5	−0.0680	0.3788	0.0868	0.049*
C6	−0.1889 (3)	0.2740 (2)	0.24050 (16)	0.0403 (4)
H6	−0.3292	0.2317	0.2038	0.048*
C7	0.1283 (3)	0.2820 (2)	0.55703 (15)	0.0359 (4)
H7A	0.1617	0.3897	0.6065	0.043*
H7B	−0.0022	0.2242	0.5932	0.043*
C8	0.4265 (3)	0.15939 (18)	0.67594 (14)	0.0301 (4)
C9	0.3600 (3)	0.23242 (19)	0.79450 (14)	0.0353 (4)
H9	0.2360	0.2968	0.7998	0.042*
C10	0.4814 (3)	0.2067 (2)	0.90146 (15)	0.0412 (4)
H10	0.4406	0.2545	0.9805	0.049*
C11	0.6648 (3)	0.1099 (2)	0.89304 (15)	0.0397 (4)
H11	0.7507	0.0930	0.9649	0.048*
C12	0.7150 (3)	0.03973 (19)	0.77449 (15)	0.0359 (4)
H12	0.8367	−0.0269	0.7683	0.043*
N1	0.6010 (2)	0.06064 (16)	0.66736 (12)	0.0334 (3)
N2	0.3221 (2)	0.18353 (16)	0.56430 (12)	0.0355 (3)
H2	0.3734	0.1384	0.4947	0.043*

	U11	U22	U33	U12	U13	U23
C1	0.0330 (9)	0.0302 (8)	0.0414 (9)	0.0009 (6)	0.0061 (7)	0.0020 (7)
C2	0.0328 (8)	0.0249 (7)	0.0354 (8)	0.0081 (6)	0.0040 (6)	0.0010 (6)
C3	0.0314 (9)	0.0348 (9)	0.0405 (9)	0.0005 (7)	0.0013 (7)	0.0026 (7)
C4	0.0443 (10)	0.0352 (9)	0.0403 (9)	0.0000 (7)	0.0100 (7)	0.0075 (7)
C5	0.0503 (11)	0.0386 (9)	0.0340 (9)	0.0075 (8)	−0.0017 (7)	0.0041 (7)
C6	0.0358 (9)	0.0403 (9)	0.0431 (10)	0.0021 (7)	−0.0041 (7)	−0.0020 (7)
C7	0.0355 (9)	0.0356 (8)	0.0378 (9)	0.0096 (7)	0.0050 (7)	0.0037 (7)
C8	0.0329 (9)	0.0249 (7)	0.0326 (8)	0.0010 (6)	0.0036 (6)	0.0033 (6)
C9	0.0410 (10)	0.0312 (8)	0.0343 (9)	0.0064 (7)	0.0064 (7)	0.0015 (6)
C10	0.0544 (11)	0.0388 (9)	0.0301 (9)	0.0045 (8)	0.0067 (7)	−0.0003 (7)
C11	0.0481 (10)	0.0382 (9)	0.0323 (9)	0.0022 (8)	−0.0039 (7)	0.0043 (7)
C12	0.0355 (9)	0.0336 (8)	0.0389 (9)	0.0032 (7)	−0.0014 (7)	0.0055 (7)
N1	0.0357 (8)	0.0328 (7)	0.0322 (7)	0.0068 (6)	0.0009 (6)	0.0022 (5)
N2	0.0416 (8)	0.0377 (7)	0.0286 (7)	0.0147 (6)	0.0023 (6)	0.0012 (6)

C1—C2	1.385 (2)	C7—H7B	0.9700
C1—C6	1.386 (2)	C8—N1	1.3502 (19)
C1—H1	0.9300	C8—N2	1.3559 (19)
C2—C3	1.395 (2)	C8—C9	1.409 (2)
C2—C7	1.500 (2)	C9—C10	1.366 (2)
C3—C4	1.378 (2)	C9—H9	0.9300
C3—H3	0.9300	C10—C11	1.383 (2)
C4—C5	1.381 (2)	C10—H10	0.9300
C4—H4	0.9300	C11—C12	1.372 (2)
C5—C6	1.380 (2)	C11—H11	0.9300
C5—H5	0.9300	C12—N1	1.3353 (19)
C6—H6	0.9300	C12—H12	0.9300
C7—N2	1.448 (2)	N2—H2	0.8600
C7—H7A	0.9700
C2—C1—C6	121.05 (15)	C2—C7—H7B	109.5
C2—C1—H1	119.5	H7A—C7—H7B	108.0
C6—C1—H1	119.5	N1—C8—N2	115.92 (13)
C1—C2—C3	118.30 (14)	N1—C8—C9	121.27 (14)
C1—C2—C7	120.76 (14)	N2—C8—C9	122.81 (14)
C3—C2—C7	120.94 (14)	C10—C9—C8	118.62 (15)
C4—C3—C2	120.63 (15)	C10—C9—H9	120.7
C4—C3—H3	119.7	C8—C9—H9	120.7
C2—C3—H3	119.7	C9—C10—C11	120.44 (15)
C3—C4—C5	120.50 (16)	C9—C10—H10	119.8
C3—C4—H4	119.8	C11—C10—H10	119.8
C5—C4—H4	119.8	C12—C11—C10	117.34 (15)
C6—C5—C4	119.57 (15)	C12—C11—H11	121.3
C6—C5—H5	120.2	C10—C11—H11	121.3
C4—C5—H5	120.2	N1—C12—C11	124.42 (15)
C5—C6—C1	119.96 (15)	N1—C12—H12	117.8
C5—C6—H6	120.0	C11—C12—H12	117.8
C1—C6—H6	120.0	C12—N1—C8	117.85 (13)
N2—C7—C2	110.93 (13)	C8—N2—C7	122.91 (13)
N2—C7—H7A	109.5	C8—N2—H2	118.5
C2—C7—H7A	109.5	C7—N2—H2	118.5
N2—C7—H7B	109.5

Cg1 and Cg2 are the centroids of the C1–C6 and N1/C8–C12 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···N1i	0.86	2.24	3.0518 (19)	157
C12—H12···Cg1i	0.93	2.72	3.536 (2)	147
C4—H4···Cg2ii	0.93	3.14	3.804 (2)	130

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C1–C6 and N1/C8–C12 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯N1i	0.86	2.24	3.0518 (19)	157
C12—H12⋯Cg1i	0.93	2.72	3.536 (2)	147
C4—H4⋯Cg2ii	0.93	3.14	3.804 (2)	130

Symmetry codes: (i) ; (ii) .