6-Methyl-pyridin-2-amine.

In the title mol-ecule, C6H8N2, the endocyclic angles are in the range 118.43 (9)-122.65 (10)°. The mol-ecular skeleton is planar (r.m.s. deviation = 0.007 Å). One of the two amino H atoms is involved in an N-H⋯N hydrogen bond, forming an inversion dimer, while the other amino H atom participates in N-H⋯π inter-actions between the dimers, forming layers parallel to (100).

Related literature

For general background to the design of chiral or acentric co-crystals, see: Jacques et al. (1981 ▶); Miyata (1991 ▶); Scheiner (1997 ▶). For related compounds, see: Büyükgüngör & Odabaşoğlu (2006 ▶); Chtioui & Jouini (2006 ▶); Ni et al. (2007 ▶); Dai et al. (2011 ▶); Waddell et al. (2011 ▶).

Experimental

Crystal data

C6H8N2

M = 108.14

Monoclinic,

a = 9.1006 (11) Å

b = 6.2458 (8) Å

c = 10.5598 (13) Å

β = 100.952 (2)°

V = 589.29 (13) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 296 K

0.30 × 0.25 × 0.20 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2003 ▶) T min = 0.977, T max = 0.985

5852 measured reflections

1420 independent reflections

1196 reflections with I > 2σ(I)

R int = 0.030

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.130

S = 1.00

1420 reflections

82 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.32 e Å−3

Δρmin = −0.16 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2001 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812047800/cv5366sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812047800/cv5366Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536812047800/cv5366Isup3.cml

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

C6H8N2	F(000) = 232
Mr = 108.14	Dx = 1.219 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2436 reflections
a = 9.1006 (11) Å	θ = 2.3–30.0°
b = 6.2458 (8) Å	µ = 0.08 mm−1
c = 10.5598 (13) Å	T = 296 K
β = 100.952 (2)°	Prism, colourless
V = 589.29 (13) Å3	0.30 × 0.25 × 0.20 mm
Z = 4

Bruker APEXII CCD diffractometer	1420 independent reflections
Radiation source: fine-focus sealed tube	1196 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.030
φ and ω scans	θmax = 28.0°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	h = −12→12
Tmin = 0.977, Tmax = 0.985	k = −8→8
5852 measured reflections	l = −13→13

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)] = 0.043	Hydrogen site location: difference Fourier map
wR(F2) = 0.130	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	w = 1/[σ2(Fo2) + (0.082P)2 + 0.126P] where P = (Fo2 + 2Fc2)/3
1420 reflections	(Δ/σ)max < 0.001
82 parameters	Δρmax = 0.32 e Å−3
0 restraints	Δρmin = −0.16 e Å−3

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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 > σ(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
N1	0.17331 (10)	0.50475 (14)	0.92049 (8)	0.0227 (3)
N2	−0.00315 (12)	0.77129 (17)	0.90952 (10)	0.0311 (3)
H2A	−0.0502 (18)	0.693 (3)	0.9607 (16)	0.040 (4)*
H2B	−0.0533 (18)	0.877 (3)	0.8697 (15)	0.038 (4)*
C2	0.11252 (12)	0.68485 (17)	0.86263 (10)	0.0234 (3)
C3	0.16561 (13)	0.77898 (18)	0.75860 (11)	0.0271 (3)
H3	0.1219	0.9029	0.7196	0.033*
C4	0.28303 (13)	0.68378 (19)	0.71621 (10)	0.0281 (3)
H4	0.3191	0.7419	0.6470	0.034*
C5	0.34831 (12)	0.49983 (18)	0.77700 (10)	0.0267 (3)
H5	0.4291	0.4349	0.7500	0.032*
C6	0.29036 (12)	0.41577 (17)	0.87838 (10)	0.0234 (3)
C7	0.35535 (13)	0.21888 (19)	0.94938 (11)	0.0307 (3)
H7A	0.4172	0.2597	1.0298	0.046*
H7B	0.4146	0.1429	0.8980	0.046*
H7C	0.2758	0.1282	0.9656	0.046*

	U11	U22	U33	U12	U13	U23
N1	0.0270 (5)	0.0204 (4)	0.0207 (4)	0.0013 (3)	0.0052 (3)	−0.0013 (3)
N2	0.0372 (6)	0.0251 (5)	0.0331 (5)	0.0101 (4)	0.0122 (4)	0.0046 (4)
C2	0.0256 (5)	0.0207 (5)	0.0233 (5)	−0.0009 (4)	0.0029 (4)	−0.0030 (4)
C3	0.0292 (6)	0.0236 (5)	0.0271 (5)	−0.0005 (4)	0.0018 (4)	0.0045 (4)
C4	0.0271 (6)	0.0331 (6)	0.0240 (5)	−0.0056 (4)	0.0047 (4)	0.0045 (4)
C5	0.0243 (5)	0.0315 (6)	0.0251 (5)	0.0014 (4)	0.0065 (4)	−0.0009 (4)
C6	0.0254 (5)	0.0225 (5)	0.0218 (5)	0.0002 (4)	0.0031 (4)	−0.0027 (4)
C7	0.0351 (6)	0.0269 (6)	0.0316 (6)	0.0078 (5)	0.0098 (5)	0.0031 (4)

N1—C2	1.3476 (14)	C4—C5	1.3929 (16)
N1—C6	1.3496 (13)	C4—H4	0.9300
N2—C2	1.3575 (14)	C5—C6	1.3837 (15)
N2—H2A	0.896 (17)	C5—H5	0.9300
N2—H2B	0.867 (17)	C6—C7	1.5019 (15)
C2—C3	1.4099 (15)	C7—H7A	0.9600
C3—C4	1.3702 (16)	C7—H7B	0.9600
C3—H3	0.9300	C7—H7C	0.9600
C2—N1—C6	118.43 (9)	C6—C5—C4	118.53 (10)
C2—N2—H2A	119.7 (10)	C6—C5—H5	120.7
C2—N2—H2B	120.1 (10)	C4—C5—H5	120.7
H2A—N2—H2B	116.2 (14)	N1—C6—C5	122.65 (10)
N1—C2—N2	116.52 (10)	N1—C6—C7	115.68 (9)
N1—C2—C3	121.96 (10)	C5—C6—C7	121.67 (10)
N2—C2—C3	121.51 (10)	C6—C7—H7A	109.5
C4—C3—C2	118.53 (10)	C6—C7—H7B	109.5
C4—C3—H3	120.7	H7A—C7—H7B	109.5
C2—C3—H3	120.7	C6—C7—H7C	109.5
C3—C4—C5	119.88 (10)	H7A—C7—H7C	109.5
C3—C4—H4	120.1	H7B—C7—H7C	109.5
C5—C4—H4	120.1
C6—N1—C2—N2	−178.81 (9)	C3—C4—C5—C6	1.01 (17)
C6—N1—C2—C3	1.34 (15)	C2—N1—C6—C5	−1.20 (16)
N1—C2—C3—C4	−0.31 (17)	C2—N1—C6—C7	178.40 (9)
N2—C2—C3—C4	179.84 (10)	C4—C5—C6—N1	0.04 (17)
C2—C3—C4—C5	−0.88 (17)	C4—C5—C6—C7	−179.54 (10)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···N1i	0.896 (17)	2.211 (17)	3.1062 (14)	177.5 (11)
N2—H2B···Cgii	0.867 (17)	2.674 (16)	3.4875 (12)	163.5 (11)

Table 1

Hydrogen-bond geometry (Å, °)

Cg is the centroid of the N1/C2–C6 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯N1i	0.896 (17)	2.211 (17)	3.1062 (14)	177.5 (11)
N2—H2B⋯Cg ii	0.867 (17)	2.674 (16)	3.4875 (12)	163.5 (11)

Symmetry codes: (i) ; (ii) .