4-Amino-pyridinium azide 4-amino-pyridine solvate.

In the title compound, C(5)H(7)N(2) (+)·N(3) (-)·C(5)H(6)N(2), all N atoms of the azide anion are situated on a twofold rotational axis, so the 4-amino-pyridinium cation and 4-amino-pyridine mol-ecule, being related by symmetry, occupy one position in the asymmetric unit. Inter-molecular N-H⋯N hydrogen bonds generate a three-dimensional hydrogen-bonding network which consolidates the crystal packing.

Related literature

For a related compound, see: Teulon et al. (1985 ▶).

Experimental

Crystal data

C5H7N2 +·n class="Chemical">N3 −·C5H6N2

M = 231.27

Monoclinic,

a = 7.507 (3) Å

b = 12.247 (5) Å

c = 13.634 (5) Å

β = 99.278 (5)°

V = 1237.0 (8) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 291 K

0.14 × 0.11 × 0.10 mm

Data collection

Bruker SMART 1K CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T min = 0.988, T max = 0.992

3027 measured reflections

1096 independent reflections

852 reflections with I > 2σ(I)

R int = 0.072

Refinement

R[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.105

S = 1.08

1096 reflections

80 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.11 e Å−3

Δρmin = −0.11 e Å−3

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); data reduction: SAIn class="Chemical">NT; 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.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810044843/cv2787sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810044843/cv2787Isup2.hkl

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

C5H7N2+·N3−·C5H6N2	F(000) = 488
Mr = 231.27	Dx = 1.242 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 1359 reflections
a = 7.507 (3) Å	θ = 3.0–25.4°
b = 12.247 (5) Å	µ = 0.08 mm−1
c = 13.634 (5) Å	T = 291 K
β = 99.278 (5)°	Block, colourless
V = 1237.0 (8) Å3	0.14 × 0.11 × 0.10 mm
Z = 4

Bruker SMART 1K CCD area-detector diffractometer	1096 independent reflections
Radiation source: fine-focus sealed tube	852 reflections with I > 2σ(I)
graphite	Rint = 0.072
φ and ω scans	θmax = 25.0°, θmin = 3.0°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −8→8
Tmin = 0.988, Tmax = 0.992	k = −12→14
3027 measured reflections	l = −16→15

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.036	H-atom parameters constrained
wR(F2) = 0.105	w = 1/[σ2(Fo2) + (0.0493P)2 + 0.0478P] where P = (Fo2 + 2Fc2)/3
S = 1.08	(Δ/σ)max < 0.001
1096 reflections	Δρmax = 0.11 e Å−3
80 parameters	Δρmin = −0.11 e Å−3
1 restraint	Extinction correction: SHELXTL (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.042 (5)

Experimental. The structure was solved by direct methods (Bruker, 2000) and successive difference Fourier syntheses.

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	Occ. (<1)
C1	0.1721 (2)	0.05406 (12)	−0.09812 (12)	0.0879 (5)
H1	0.2321	0.0033	−0.1316	0.106*
C2	0.22248 (18)	0.06466 (10)	0.00146 (11)	0.0780 (4)
H2	0.3145	0.0214	0.0350	0.094*
C3	0.13523 (16)	0.14103 (10)	0.05345 (9)	0.0699 (4)
C4	−0.00162 (18)	0.20282 (11)	−0.00180 (11)	0.0791 (4)
H4	−0.0635	0.2547	0.0294	0.095*
C5	−0.0439 (2)	0.18672 (13)	−0.10131 (12)	0.0932 (5)
H5	−0.1355	0.2286	−0.1371	0.112*
N1	0.18164 (16)	0.15416 (9)	0.15211 (9)	0.0858 (4)
H1A	0.1265	0.2016	0.1828	0.103*
H1B	0.2665	0.1151	0.1846	0.103*
N2	0.04055 (19)	0.11306 (11)	−0.15027 (9)	0.0948 (4)
H2A	0.0108	0.1042	−0.2134	0.114*	0.50
N3	0.5000	−0.02503 (17)	0.7500	0.1009 (6)
N4	0.5000	0.07152 (17)	0.7500	0.0760 (5)
N5	0.5000	0.16656 (17)	0.7500	0.1062 (6)

	U11	U22	U33	U12	U13	U23
C1	0.0948 (10)	0.0867 (9)	0.0891 (8)	−0.0181 (8)	0.0353 (8)	−0.0118 (8)
C2	0.0744 (8)	0.0752 (8)	0.0879 (8)	−0.0108 (6)	0.0231 (6)	−0.0057 (6)
C3	0.0681 (7)	0.0682 (7)	0.0762 (9)	−0.0163 (6)	0.0206 (6)	−0.0037 (6)
C4	0.0765 (8)	0.0799 (8)	0.0834 (9)	−0.0071 (6)	0.0205 (7)	−0.0009 (7)
C5	0.0938 (10)	0.1000 (11)	0.0854 (11)	−0.0100 (8)	0.0132 (8)	0.0090 (8)
N1	0.0900 (8)	0.0873 (8)	0.0803 (8)	0.0016 (5)	0.0144 (6)	−0.0086 (6)
N2	0.1105 (10)	0.1050 (9)	0.0714 (8)	−0.0251 (7)	0.0223 (7)	−0.0032 (7)
N3	0.0964 (13)	0.0868 (12)	0.1185 (15)	0.000	0.0141 (10)	0.000
N4	0.0626 (9)	0.0993 (13)	0.0671 (9)	0.000	0.0139 (6)	0.000
N5	0.1123 (14)	0.0918 (14)	0.1242 (16)	0.000	0.0488 (12)	0.000

C1—N2	1.333 (2)	C4—H4	0.9300
C1—C2	1.356 (2)	C5—N2	1.341 (2)
C1—H1	0.9300	C5—H5	0.9300
C2—C3	1.3985 (18)	N1—H1A	0.8600
C2—H2	0.9300	N1—H1B	0.8600
C3—N1	1.3437 (17)	N2—H2A	0.8600
C3—C4	1.395 (2)	N3—N4	1.182 (3)
C4—C5	1.357 (2)	N4—N5	1.164 (2)
N2—C1—C2	123.06 (14)	C3—C4—H4	120.2
N2—C1—H1	118.5	N2—C5—C4	122.83 (15)
C2—C1—H1	118.5	N2—C5—H5	118.6
C1—C2—C3	119.58 (14)	C4—C5—H5	118.6
C1—C2—H2	120.2	C3—N1—H1A	120.0
C3—C2—H2	120.2	C3—N1—H1B	120.0
N1—C3—C4	121.68 (12)	H1A—N1—H1B	120.0
N1—C3—C2	121.36 (13)	C1—N2—C5	117.93 (13)
C4—C3—C2	116.97 (13)	C1—N2—H2A	121.0
C5—C4—C3	119.63 (14)	C5—N2—H2A	121.0
C5—C4—H4	120.2	N5—N4—N3	180.000 (1)
N2—C1—C2—C3	−0.5 (2)	C2—C3—C4—C5	0.10 (18)
C1—C2—C3—N1	−179.81 (11)	C3—C4—C5—N2	0.0 (2)
C1—C2—C3—C4	0.11 (17)	C2—C1—N2—C5	0.6 (2)
N1—C3—C4—C5	−179.98 (11)	C4—C5—N2—C1	−0.3 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···N5i	0.86	2.15	3.008 (2)	174
N1—H1B···N3ii	0.86	2.14	2.9942 (18)	172
N2—H2A···N2iii	0.86	1.84	2.689 (3)	169

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯N5i	0.86	2.15	3.008 (2)	174
N1—H1B⋯N3ii	0.86	2.14	2.9942 (18)	172
N2—H2A⋯N2iii	0.86	1.84	2.689 (3)	169

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