N-(5-Amino-1H-tetra-zol-1-yl)formamide.

In the title compound, C(2)H(4)N(6)O, the planar [maximum deviation = 0.006 (2) Å] amino-tetra-zole group makes a dihedral angle of 83.65 (8)° with the formamide unit. In the crystal structure, inter-molecular N-H⋯N, N-H⋯O and C-H⋯N hydrogen bonds are responsible for the formation of a three-dimensional network.

Related literature

For energetic nitro­gen-rich derivatives of 1,5-diamino­tetra­zole, see: Joo et al. (2008 ▶). For nitro­gen-rich metastable green chemistry compounds, see: Steinhauser et al. (2008 ▶). For 1,5-diamino-1H-tetra­zole derivatives, see: Galvez-Ruiz et al. (2005 ▶). For the structure of N-(1-diacetyl­amino-1H-tetra­zol-5-yl)-acetamide, see: He et al. (2009 ▶).

Experimental

Crystal data

C2H4N6O

M = 128.11

Orthorhombic,

a = 10.232 (10) Å

b = 12.054 (12) Å

c = 4.208 (4) Å

V = 519.1 (9) Å3

Z = 4

Mo Kα radiation

μ = 0.14 mm−1

T = 93 K

0.47 × 0.27 × 0.07 mm

Data collection

Rigaku Saturn724+ diffractometer

Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ▶) T min = 0.940, T max = 0.991

3464 measured reflections

659 independent reflections

545 reflections with I > 2σ(I)

R int = 0.051

Refinement

R[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.089

S = 1.00

659 reflections

94 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.22 e Å−3

Δρmin = −0.19 e Å−3

Data collection: CrystalClear (Rigaku, 2008 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809044833/si2213sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809044833/si2213Isup2.hkl

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

C2H4N6O	F(000) = 264
Mr = 128.11	Dx = 1.639 Mg m−3
Orthorhombic, Pnn2	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2 -2n	Cell parameters from 1548 reflections
a = 10.232 (10) Å	θ = 3.4–27.2°
b = 12.054 (12) Å	µ = 0.14 mm−1
c = 4.208 (4) Å	T = 93 K
V = 519.1 (9) Å3	Platelet, colorless
Z = 4	0.47 × 0.27 × 0.07 mm

Rigaku Saturn724+ diffractometer	659 independent reflections
Radiation source: Rotating Anode	545 reflections with I > 2σ(I)
graphite	Rint = 0.051
Detector resolution: 28.5714 pixels mm-1	θmax = 27.3°, θmin = 3.4°
multi–scan	h = −13→12
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	k = −15→14
Tmin = 0.940, Tmax = 0.991	l = −5→5
3464 measured reflections

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) = 0.089	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	w = 1/[σ2(Fo2) + (0.0522P)2] where P = (Fo2 + 2Fc2)/3
659 reflections	(Δ/σ)max < 0.001
94 parameters	Δρmax = 0.22 e Å−3
1 restraint	Δρmin = −0.19 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
O1	0.32520 (17)	0.52017 (15)	0.4700 (5)	0.0250 (5)
N1	0.53348 (19)	0.80213 (18)	0.7377 (6)	0.0200 (5)
N2	0.4393 (2)	0.85281 (17)	0.5557 (6)	0.0219 (5)
N3	0.3276 (2)	0.80311 (18)	0.5797 (6)	0.0213 (5)
N4	0.34795 (18)	0.71697 (17)	0.7884 (6)	0.0177 (5)
N5	0.2526 (2)	0.6400 (2)	0.8533 (6)	0.0189 (5)
N6	0.5250 (2)	0.64294 (19)	1.0818 (6)	0.0210 (5)
C1	0.4751 (2)	0.7167 (2)	0.8815 (6)	0.0178 (6)
C2	0.2470 (2)	0.5459 (2)	0.6773 (7)	0.0203 (6)
H2	0.1769	0.4961	0.7180	0.024*
H5N	0.196 (3)	0.661 (2)	0.986 (9)	0.028 (8)*
H6A	0.607 (3)	0.645 (2)	1.134 (8)	0.043 (10)*
H6B	0.473 (3)	0.596 (2)	1.192 (8)	0.028 (9)*

	U11	U22	U33	U12	U13	U23
O1	0.0209 (11)	0.0284 (10)	0.0259 (11)	−0.0004 (8)	0.0050 (9)	−0.0016 (9)
N1	0.0113 (10)	0.0261 (12)	0.0226 (13)	0.0013 (8)	0.0011 (10)	0.0021 (11)
N2	0.0133 (10)	0.0263 (12)	0.0262 (14)	0.0021 (9)	0.0010 (11)	0.0016 (11)
N3	0.0137 (11)	0.0257 (11)	0.0247 (13)	0.0006 (8)	0.0006 (10)	0.0051 (11)
N4	0.0093 (10)	0.0220 (11)	0.0216 (12)	−0.0009 (8)	0.0009 (10)	0.0012 (10)
N5	0.0090 (10)	0.0269 (12)	0.0209 (13)	−0.0011 (8)	0.0050 (9)	0.0021 (10)
N6	0.0116 (10)	0.0265 (12)	0.0250 (14)	−0.0001 (9)	−0.0023 (10)	0.0025 (11)
C1	0.0107 (11)	0.0229 (13)	0.0198 (15)	0.0027 (9)	0.0004 (11)	−0.0028 (11)
C2	0.0143 (12)	0.0233 (15)	0.0232 (13)	−0.0014 (10)	−0.0013 (11)	0.0058 (13)

O1—C2	1.224 (3)	N5—C2	1.356 (4)
N1—C1	1.335 (3)	N5—H5N	0.84 (4)
N1—N2	1.374 (3)	N6—C1	1.328 (4)
N2—N3	1.294 (3)	N6—H6A	0.87 (4)
N3—N4	1.376 (3)	N6—H6B	0.90 (3)
N4—C1	1.359 (3)	C2—H2	0.9500
N4—N5	1.374 (3)
C1—N1—N2	106.4 (2)	C1—N6—H6A	121 (2)
N3—N2—N1	111.7 (2)	C1—N6—H6B	121 (2)
N2—N3—N4	105.4 (2)	H6A—N6—H6B	117 (3)
C1—N4—N5	128.4 (2)	N6—C1—N1	129.2 (2)
C1—N4—N3	109.3 (2)	N6—C1—N4	123.6 (2)
N5—N4—N3	122.0 (2)	N1—C1—N4	107.2 (2)
C2—N5—N4	119.1 (2)	O1—C2—N5	125.0 (2)
C2—N5—H5N	126.0 (19)	O1—C2—H2	117.5
N4—N5—H5N	114.4 (19)	N5—C2—H2	117.5
C1—N1—N2—N3	−0.2 (3)	N2—N1—C1—N4	−0.4 (3)
N1—N2—N3—N4	0.7 (3)	N5—N4—C1—N6	−6.3 (4)
N2—N3—N4—C1	−1.0 (3)	N3—N4—C1—N6	−179.7 (2)
N2—N3—N4—N5	−174.8 (2)	N5—N4—C1—N1	174.2 (3)
C1—N4—N5—C2	−81.1 (3)	N3—N4—C1—N1	0.9 (3)
N3—N4—N5—C2	91.4 (3)	N4—N5—C2—O1	3.8 (4)
N2—N1—C1—N6	−179.9 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N5—H5N···N1i	0.84 (3)	2.02 (3)	2.851 (4)	168 (3)
N6—H6A···O1ii	0.87 (3)	2.54 (3)	2.981 (4)	113 (2)
N6—H6A···N3iii	0.87 (3)	2.35 (3)	3.164 (4)	156 (3)
N6—H6B···O1iv	0.91 (3)	2.12 (3)	3.006 (4)	167 (2)
C2—H2···N2v	0.95	2.53	3.404 (5)	152

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N5—H5N⋯N1i	0.84 (3)	2.02 (3)	2.851 (4)	168 (3)
N6—H6A⋯O1ii	0.87 (3)	2.54 (3)	2.981 (4)	113 (2)
N6—H6A⋯N3iii	0.87 (3)	2.35 (3)	3.164 (4)	156 (3)
N6—H6B⋯O1iv	0.91 (3)	2.12 (3)	3.006 (4)	167 (2)
C2—H2⋯N2v	0.95	2.53	3.404 (5)	152

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