Pyridine-2,5-diamine.

In the title mol-ecule, C5H7N3, intra-cyclic angles cover the range 117.15 (10)-124.03 (11)°. The N atoms of the amino groups have trigonal-pyramidal configurations deviating slightly from the pyridine plane by 0.106 (2) and -0.042 (2) Å. In the crystal, the pyridine N atom serves as an acceptor of an N-H⋯N hydrogen bond which links two mol-ecules into a centrosymmetric dimer. Inter-molecular N-H⋯N hydrogen bonds between the amino groups further consolidate the crystal packing, forming a three-dimensional network.

Related literature

For general background, see: Domenicano et al. (1975 ▶); Domenicano & Vaciago (1979 ▶); Mootz & Wussow (1981 ▶); Crawford et al. (2009 ▶). For the crystal structures of isomeric diamino­pyridines, see: Schwalbe et al. (1987 ▶); Rubin-Preminger & Englert (2007 ▶); Al-Dajani et al. (2009 ▶); Betz et al. (2011 ▶).

Experimental

Crystal data

C5H7N3

M = 109.14

Orthorhombic,

a = 11.4447 (11) Å

b = 7.1447 (7) Å

c = 12.8030 (12) Å

V = 1046.89 (17) Å3

Z = 8

Mo Kα radiation

μ = 0.09 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 = 0.973, T max = 0.982

13022 measured reflections

1595 independent reflections

1240 reflections with I > 2σ(I)

R int = 0.049

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.109

S = 1.01

1595 reflections

85 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.36 e Å−3

Δρmin = −0.24 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/S1600536812046260/cv5359sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812046260/cv5359Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536812046260/cv5359Isup3.cml

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

C5H7N3	F(000) = 464
Mr = 109.14	Dx = 1.385 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 2334 reflections
a = 11.4447 (11) Å	θ = 3.2–28.8°
b = 7.1447 (7) Å	µ = 0.09 mm−1
c = 12.8030 (12) Å	T = 296 K
V = 1046.89 (17) Å3	Prism, red
Z = 8	0.30 × 0.25 × 0.20 mm

Bruker APEXII CCD diffractometer	1595 independent reflections
Radiation source: fine-focus sealed tube	1240 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.049
φ and ω scans	θmax = 30.5°, θmin = 3.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	h = −16→16
Tmin = 0.973, Tmax = 0.982	k = −10→10
13022 measured reflections	l = −18→18

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: difference Fourier map
wR(F2) = 0.109	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	w = 1/[σ2(Fo2) + (0.0475P)2 + 0.63P] where P = (Fo2 + 2Fc2)/3
1595 reflections	(Δ/σ)max < 0.001
85 parameters	Δρmax = 0.36 e Å−3
0 restraints	Δρmin = −0.24 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	0.46050 (8)	0.50612 (15)	0.35845 (8)	0.0150 (2)
N2	0.36236 (10)	0.66538 (15)	0.49098 (8)	0.0167 (2)
H2A	0.4111 (14)	0.610 (2)	0.5333 (13)	0.020*
H2B	0.2925 (15)	0.674 (2)	0.5190 (12)	0.020*
N3	0.38898 (10)	0.41571 (15)	0.07954 (8)	0.0164 (2)
H3A	0.3841 (13)	0.510 (2)	0.0337 (12)	0.020*
H3B	0.4559 (15)	0.352 (2)	0.0701 (12)	0.020*
C2	0.36402 (10)	0.59703 (16)	0.38919 (9)	0.0139 (2)
C3	0.27102 (10)	0.63298 (17)	0.32018 (9)	0.0148 (2)
H3	0.2045	0.6952	0.3433	0.018*
C4	0.28001 (10)	0.57463 (16)	0.21780 (9)	0.0150 (2)
H4	0.2192	0.5971	0.1712	0.018*
C5	0.38092 (10)	0.48140 (16)	0.18414 (9)	0.0139 (2)
C6	0.46769 (10)	0.45101 (17)	0.25771 (9)	0.0148 (2)
H6	0.5350	0.3889	0.2364	0.018*

	U11	U22	U33	U12	U13	U23
N1	0.0139 (5)	0.0159 (5)	0.0154 (5)	−0.0001 (4)	−0.0006 (4)	0.0002 (4)
N2	0.0162 (5)	0.0189 (5)	0.0150 (5)	0.0022 (4)	−0.0009 (4)	−0.0008 (4)
N3	0.0163 (5)	0.0190 (5)	0.0137 (5)	0.0027 (4)	0.0005 (4)	0.0003 (4)
C2	0.0148 (5)	0.0120 (5)	0.0148 (5)	−0.0018 (4)	0.0007 (4)	0.0006 (4)
C3	0.0130 (5)	0.0138 (5)	0.0176 (5)	0.0010 (4)	0.0003 (4)	0.0012 (4)
C4	0.0134 (5)	0.0138 (5)	0.0177 (5)	0.0001 (4)	−0.0024 (4)	0.0018 (4)
C5	0.0148 (5)	0.0124 (5)	0.0143 (5)	−0.0013 (4)	0.0008 (4)	0.0008 (4)
C6	0.0122 (5)	0.0154 (5)	0.0169 (5)	0.0007 (4)	0.0009 (4)	0.0003 (4)

N1—C2	1.3401 (15)	C2—C3	1.4069 (16)
N1—C6	1.3510 (15)	C3—C4	1.3793 (16)
N2—C2	1.3919 (15)	C3—H3	0.9300
N2—H2A	0.874 (17)	C4—C5	1.4011 (16)
N2—H2B	0.879 (17)	C4—H4	0.9300
N3—C5	1.4221 (15)	C5—C6	1.3859 (16)
N3—H3A	0.894 (16)	C6—H6	0.9300
N3—H3B	0.898 (17)
C2—N1—C6	118.15 (10)	C4—C3—H3	120.5
C2—N2—H2A	114.3 (11)	C2—C3—H3	120.5
C2—N2—H2B	114.8 (10)	C3—C4—C5	119.83 (11)
H2A—N2—H2B	111.2 (14)	C3—C4—H4	120.1
C5—N3—H3A	111.4 (10)	C5—C4—H4	120.1
C5—N3—H3B	110.4 (10)	C6—C5—C4	117.13 (10)
H3A—N3—H3B	110.2 (14)	C6—C5—N3	122.81 (11)
N1—C2—N2	117.15 (10)	C4—C5—N3	120.01 (10)
N1—C2—C3	121.83 (11)	N1—C6—C5	124.03 (11)
N2—C2—C3	120.90 (11)	N1—C6—H6	118.0
C4—C3—C2	119.02 (11)	C5—C6—H6	118.0
C6—N1—C2—N2	−175.08 (11)	C3—C4—C5—C6	0.54 (16)
C6—N1—C2—C3	0.96 (17)	C3—C4—C5—N3	177.98 (11)
N1—C2—C3—C4	−0.66 (17)	C2—N1—C6—C5	−0.51 (17)
N2—C2—C3—C4	175.23 (11)	C4—C5—C6—N1	−0.23 (17)
C2—C3—C4—C5	−0.12 (17)	N3—C5—C6—N1	−177.60 (11)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···N1i	0.874 (17)	2.183 (17)	3.0541 (15)	175.1 (10)
N2—H2B···N3ii	0.879 (17)	2.309 (17)	3.1457 (16)	159.3 (10)
N3—H3A···N2iii	0.894 (16)	2.397 (17)	3.2150 (16)	152.2 (10)
N3—H3B···N2iv	0.898 (17)	2.593 (17)	3.4803 (16)	170.0 (10)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯N1i	0.874 (17)	2.183 (17)	3.0541 (15)	175.1 (10)
N2—H2B⋯N3ii	0.879 (17)	2.309 (17)	3.1457 (16)	159.3 (10)
N3—H3A⋯N2iii	0.894 (16)	2.397 (17)	3.2150 (16)	152.2 (10)
N3—H3B⋯N2iv	0.898 (17)	2.593 (17)	3.4803 (16)	170.0 (10)

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