Pyridine-2,3-diamine.

The mol-ecule of the title pyridine derivative, C(5)H(7)N(3), shows approximately non-crystallographic C(s) symmetry. Intra-cyclic angles cover the range 117.50 (14)-123.03 (15)°. In the crystal, N-H⋯N hydrogen bonds connect mol-ecules into a three-dimensional network. The closest inter-centroid distance between two π-systems occurs with the c-axis repeat at 3.9064 (12) Å.

Related literature

For the crystal structure of the dihydro­chloride of the title compound, see: Hemamalini & Fun (2010 ▶). For the crystal structures of Zn complexes of the title compound, see: de Cires-Mejias et al. (2004 ▶). For graph-set analysis of hydrogen bonds, see: Etter et al. (1990 ▶); Bernstein et al. (1995 ▶).

Experimental

Crystal data

C5H7N3

M = 109.14

Tetragonal,

a = 16.4670 (3) Å

c = 3.9064 (12) Å

V = 1059.3 (3) Å3

Z = 8

Mo Kα radiation

μ = 0.09 mm−1

T = 200 K

0.48 × 0.16 × 0.11 mm

Data collection

Bruker APEXII CCD diffractometer

9864 measured reflections

754 independent reflections

706 reflections with I > 2σ(I)

R int = 0.047

Refinement

R[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.085

S = 1.10

754 reflections

89 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.23 e Å−3

Δρmin = −0.17 e Å−3

Data collection: APEX2 (Bruker, 2010 ▶); cell refinement: SAINT (Bruker, 2010 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811029412/om2449sup1.cif

Supplementary material file. DOI: 10.1107/S1600536811029412/om2449Isup2.cdx

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811029412/om2449Isup3.hkl

Supplementary material file. DOI: 10.1107/S1600536811029412/om2449Isup4.cml

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

C5H7N3	Dx = 1.369 Mg m−3
Mr = 109.14	Mo Kα radiation, λ = 0.71073 Å
Tetragonal, P42bc	Cell parameters from 5917 reflections
Hall symbol: P 4c -2ab	θ = 2.5–28.3°
a = 16.4670 (3) Å	µ = 0.09 mm−1
c = 3.9064 (12) Å	T = 200 K
V = 1059.3 (3) Å3	Needle, brown
Z = 8	0.48 × 0.16 × 0.11 mm
F(000) = 464

Bruker APEXII CCD diffractometer	706 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.047
graphite	θmax = 28.3°, θmin = 1.8°
φ and ω scans	h = −21→20
9864 measured reflections	k = −21→21
754 independent reflections	l = −5→5

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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.085	H atoms treated by a mixture of independent and constrained refinement
S = 1.10	w = 1/[σ2(Fo2) + (0.0428P)2 + 0.2489P] where P = (Fo2 + 2Fc2)/3
754 reflections	(Δ/σ)max < 0.001
89 parameters	Δρmax = 0.23 e Å−3
1 restraint	Δρmin = −0.17 e Å−3

	x	y	z	Uiso*/Ueq
N1	0.20596 (8)	−0.05610 (8)	0.9243 (5)	0.0268 (3)
N2	0.11296 (8)	0.04458 (9)	1.0621 (5)	0.0271 (3)
H21	0.1094 (13)	0.0921 (14)	1.156 (8)	0.040 (6)*
H22	0.0934 (12)	0.0063 (14)	1.184 (7)	0.037 (6)*
N3	0.21809 (9)	0.16454 (9)	0.7974 (5)	0.0302 (4)
H31	0.1677 (13)	0.1730 (12)	0.757 (7)	0.033 (5)*
H32	0.2471 (12)	0.1946 (12)	0.652 (8)	0.038 (6)*
C1	0.18758 (9)	0.02266 (9)	0.9286 (5)	0.0225 (4)
C2	0.23965 (9)	0.08211 (9)	0.7834 (6)	0.0240 (3)
C3	0.31167 (10)	0.05570 (10)	0.6425 (5)	0.0283 (4)
H3	0.3478	0.0938	0.5417	0.034*
C4	0.33173 (10)	−0.02631 (11)	0.6469 (6)	0.0307 (4)
H4	0.3819	−0.0449	0.5556	0.037*
C5	0.27702 (10)	−0.07971 (10)	0.7870 (6)	0.0300 (4)
H5	0.2900	−0.1359	0.7869	0.036*

	U11	U22	U33	U12	U13	U23
N1	0.0256 (7)	0.0250 (7)	0.0298 (8)	0.0002 (5)	−0.0024 (7)	0.0000 (7)
N2	0.0250 (7)	0.0249 (7)	0.0315 (8)	−0.0003 (5)	0.0025 (6)	−0.0013 (7)
N3	0.0276 (7)	0.0256 (7)	0.0374 (9)	−0.0023 (5)	−0.0009 (8)	0.0039 (8)
C1	0.0214 (7)	0.0252 (7)	0.0209 (8)	−0.0013 (5)	−0.0042 (7)	−0.0005 (7)
C2	0.0238 (7)	0.0267 (7)	0.0217 (7)	−0.0032 (5)	−0.0040 (7)	0.0003 (8)
C3	0.0261 (8)	0.0357 (8)	0.0231 (8)	−0.0065 (6)	−0.0014 (8)	0.0009 (8)
C4	0.0242 (7)	0.0411 (9)	0.0268 (9)	0.0024 (6)	0.0012 (8)	−0.0044 (9)
C5	0.0288 (8)	0.0278 (8)	0.0334 (9)	0.0045 (6)	−0.0023 (10)	−0.0021 (9)

N1—C1	1.332 (2)	C1—C2	1.420 (2)
N1—C5	1.345 (2)	C2—C3	1.378 (2)
N2—C1	1.383 (2)	C3—C4	1.390 (2)
N2—H21	0.87 (2)	C3—H3	0.9500
N2—H22	0.85 (2)	C4—C5	1.373 (3)
N3—C2	1.404 (2)	C4—H4	0.9500
N3—H31	0.86 (2)	C5—H5	0.9500
N3—H32	0.89 (3)
C1—N1—C5	118.97 (15)	C3—C2—C1	117.50 (14)
C1—N2—H21	117.1 (15)	N3—C2—C1	119.89 (16)
C1—N2—H22	110.7 (14)	C2—C3—C4	120.41 (16)
H21—N2—H22	114 (2)	C2—C3—H3	119.8
C2—N3—H31	113.3 (13)	C4—C3—H3	119.8
C2—N3—H32	112.2 (14)	C5—C4—C3	118.11 (16)
H31—N3—H32	108 (2)	C5—C4—H4	120.9
N1—C1—N2	117.44 (15)	C3—C4—H4	120.9
N1—C1—C2	121.95 (15)	N1—C5—C4	123.03 (15)
N2—C1—C2	120.49 (14)	N1—C5—H5	118.5
C3—C2—N3	122.57 (16)	C4—C5—H5	118.5
C5—N1—C1—N2	178.05 (17)	N3—C2—C3—C4	177.43 (19)
C5—N1—C1—C2	1.9 (3)	C1—C2—C3—C4	−0.4 (3)
N1—C1—C2—C3	−1.4 (3)	C2—C3—C4—C5	1.6 (3)
N2—C1—C2—C3	−177.42 (18)	C1—N1—C5—C4	−0.6 (3)
N1—C1—C2—N3	−179.3 (2)	C3—C4—C5—N1	−1.1 (3)
N2—C1—C2—N3	4.7 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H21···N1i	0.87 (2)	2.32 (2)	3.153 (2)	161.2 (19)
N2—H22···N2ii	0.85 (2)	2.58 (2)	3.4369 (16)	175.9 (18)
N3—H31···N1iii	0.86 (2)	2.32 (2)	3.115 (2)	156 (2)
N3—H32···N3iv	0.89 (3)	2.47 (2)	3.359 (2)	175 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H21⋯N1i	0.87 (2)	2.32 (2)	3.153 (2)	161.2 (19)
N2—H22⋯N2ii	0.85 (2)	2.58 (2)	3.4369 (16)	175.9 (18)
N3—H31⋯N1iii	0.86 (2)	2.32 (2)	3.115 (2)	156 (2)
N3—H32⋯N3iv	0.89 (3)	2.47 (2)	3.359 (2)	175 (2)

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .