N-(1-Diacetyl-amino-1H-tetra-zol-5-yl)acetamide.

In the crystal structure of the title compound, C(7)H(10)N(6)O(3), there are N-H⋯O, N-H⋯N and C-H⋯O inter-actions, generating a three-dimensional supra-molecular network structure. A short intermolecular O⋯C contact of 2.8994 (18) Å is alsopresent in the crystal structure, but no π-π contacts are observed.

Related literature

For the preparation, see: Gaponnik & Karavai (1984 ▶). For general background to the use of 1, 5-diaminotetrazole as an intermediate in the preparation of tetrazole-containing compounds with prospective applications in energetic mater­ials, see: Galvez-Ruiz et al. (2005 ▶). For hydrogen-bond-length data, see: Desiraju & Steiner (1999 ▶). For carbon­yl–carbonyl inter­actions, see: Allen et al. (1998 ▶).

Experimental

Crystal data

C7H10N6O3

M = 226.21

Monoclinic,

a = 6.973 (2) Å

b = 16.678 (5) Å

c = 8.871 (3) Å

β = 106.987 (4)°

V = 986.6 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.12 mm−1

T = 93 K

0.60 × 0.25 × 0.18 mm

Data collection

Rigaku Saturn724+ diffractometer

Absorption correction: none

7848 measured reflections

2255 independent reflections

1898 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.089

S = 1.00

2255 reflections

152 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.27 e Å−3

Δρmin = −0.31 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 global, I. DOI: 10.1107/S1600536809027421/xu2550sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809027421/xu2550Isup2.hkl

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

C7H10N6O3	F(000) = 472
Mr = 226.21	Dx = 1.523 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3214 reflections
a = 6.973 (2) Å	θ = 3.1–27.5°
b = 16.678 (5) Å	µ = 0.12 mm−1
c = 8.871 (3) Å	T = 93 K
β = 106.987 (4)°	Block, colourless
V = 986.6 (5) Å3	0.60 × 0.25 × 0.18 mm
Z = 4

Rigaku Saturn724+ diffractometer	1898 reflections with I > 2σ(I)
Radiation source: Rotating Anode	Rint = 0.028
graphite	θmax = 27.5°, θmin = 3.1°
Detector resolution: 28.5714 pixels mm-1	h = −9→8
Multi–scan	k = −21→20
7848 measured reflections	l = −11→11
2255 independent 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)] = 0.037	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) + (0.046P)2 + 0.18P] where P = (Fo2 + 2Fc2)/3
2255 reflections	(Δ/σ)max < 0.001
152 parameters	Δρmax = 0.27 e Å−3
0 restraints	Δρmin = −0.31 e Å−3

Geometry. All esds (except the esd in the dihedral angle betweeex two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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	0.98846 (13)	0.79462 (5)	0.37140 (10)	0.0163 (2)
O2	0.33700 (14)	0.66238 (7)	0.56926 (11)	0.0280 (3)
O3	0.77881 (14)	0.53886 (6)	0.89046 (10)	0.0199 (2)
N1	0.71476 (16)	0.66802 (7)	0.30010 (12)	0.0170 (2)
N2	0.60145 (16)	0.59851 (7)	0.26310 (12)	0.0182 (3)
N3	0.56513 (16)	0.56773 (6)	0.38460 (12)	0.0170 (2)
N4	0.65849 (16)	0.61680 (6)	0.50781 (12)	0.0141 (2)
N5	0.64409 (15)	0.60537 (6)	0.65826 (12)	0.0137 (2)
N6	0.85854 (15)	0.73478 (6)	0.55048 (12)	0.0147 (2)
C1	0.74742 (18)	0.67770 (7)	0.45264 (14)	0.0133 (3)
C2	0.46012 (19)	0.63385 (8)	0.68129 (15)	0.0176 (3)
C3	0.4357 (2)	0.62716 (9)	0.84238 (15)	0.0216 (3)
H3A	0.3149	0.6562	0.8459	0.026*
H3B	0.5531	0.6504	0.9195	0.026*
H3C	0.4232	0.5705	0.8676	0.026*
C4	0.79059 (19)	0.55442 (7)	0.76155 (15)	0.0153 (3)
C5	0.9522 (2)	0.52400 (8)	0.69584 (16)	0.0206 (3)
H5A	1.0570	0.4978	0.7798	0.025*
H5B	1.0104	0.5690	0.6532	0.025*
H5C	0.8949	0.4853	0.6116	0.025*
C6	0.98590 (18)	0.78772 (7)	0.50729 (14)	0.0132 (3)
C7	1.1204 (2)	0.83460 (8)	0.63980 (15)	0.0186 (3)
H7A	1.2488	0.8066	0.6799	0.022*
H7B	1.0572	0.8401	0.7245	0.022*
H7C	1.1433	0.8879	0.6019	0.022*
H6N	0.858 (2)	0.7348 (10)	0.652 (2)	0.034 (5)*

	U11	U22	U33	U12	U13	U23
O1	0.0204 (5)	0.0177 (5)	0.0116 (4)	−0.0020 (4)	0.0057 (4)	0.0007 (4)
O2	0.0230 (5)	0.0397 (6)	0.0199 (5)	0.0122 (5)	0.0039 (4)	0.0046 (4)
O3	0.0220 (5)	0.0225 (5)	0.0150 (5)	0.0013 (4)	0.0051 (4)	0.0037 (4)
N1	0.0176 (6)	0.0200 (6)	0.0128 (5)	−0.0040 (4)	0.0037 (4)	−0.0021 (4)
N2	0.0191 (6)	0.0203 (6)	0.0148 (5)	−0.0039 (4)	0.0044 (4)	−0.0020 (4)
N3	0.0186 (6)	0.0177 (6)	0.0139 (5)	−0.0034 (4)	0.0034 (4)	−0.0026 (4)
N4	0.0172 (5)	0.0152 (5)	0.0099 (5)	−0.0029 (4)	0.0040 (4)	−0.0007 (4)
N5	0.0151 (5)	0.0161 (5)	0.0106 (5)	−0.0005 (4)	0.0049 (4)	0.0016 (4)
N6	0.0181 (5)	0.0169 (6)	0.0099 (5)	−0.0042 (4)	0.0051 (4)	−0.0015 (4)
C1	0.0130 (6)	0.0143 (6)	0.0130 (6)	0.0000 (5)	0.0043 (5)	0.0011 (5)
C2	0.0167 (7)	0.0192 (7)	0.0170 (6)	−0.0001 (5)	0.0051 (5)	−0.0007 (5)
C3	0.0183 (7)	0.0295 (8)	0.0187 (7)	0.0018 (5)	0.0083 (6)	−0.0004 (6)
C4	0.0152 (7)	0.0130 (6)	0.0160 (6)	−0.0024 (5)	0.0021 (5)	−0.0005 (5)
C5	0.0185 (7)	0.0217 (7)	0.0228 (7)	0.0031 (5)	0.0079 (6)	0.0018 (6)
C6	0.0142 (6)	0.0133 (6)	0.0125 (6)	0.0022 (5)	0.0045 (5)	0.0016 (5)
C7	0.0218 (7)	0.0182 (7)	0.0154 (6)	−0.0047 (5)	0.0048 (5)	−0.0027 (5)

O1—C6	1.2164 (15)	N6—H6N	0.900 (16)
O2—C2	1.2052 (16)	C2—C3	1.4919 (18)
O3—C4	1.1987 (15)	C3—H3A	0.9800
N1—C1	1.3149 (16)	C3—H3B	0.9800
N1—N2	1.3871 (15)	C3—H3C	0.9800
N2—N3	1.2841 (15)	C4—C5	1.5004 (18)
N3—N4	1.3684 (15)	C5—H5A	0.9800
N4—C1	1.3538 (16)	C5—H5B	0.9800
N4—N5	1.3806 (14)	C5—H5C	0.9800
N5—C4	1.4346 (16)	C6—C7	1.4927 (17)
N5—C2	1.4374 (16)	C7—H7A	0.9800
N6—C1	1.3663 (16)	C7—H7B	0.9800
N6—C6	1.3834 (16)	C7—H7C	0.9800
C1—N1—N2	105.16 (10)	C2—C3—H3C	109.5
N3—N2—N1	111.96 (10)	H3A—C3—H3C	109.5
N2—N3—N4	105.48 (10)	H3B—C3—H3C	109.5
C1—N4—N3	108.73 (10)	O3—C4—N5	120.21 (12)
C1—N4—N5	128.57 (10)	O3—C4—C5	124.47 (12)
N3—N4—N5	122.52 (10)	N5—C4—C5	115.32 (11)
N4—N5—C4	117.38 (10)	C4—C5—H5A	109.5
N4—N5—C2	114.32 (10)	C4—C5—H5B	109.5
C4—N5—C2	127.12 (10)	H5A—C5—H5B	109.5
C1—N6—C6	124.02 (11)	C4—C5—H5C	109.5
C1—N6—H6N	117.8 (11)	H5A—C5—H5C	109.5
C6—N6—H6N	117.9 (11)	H5B—C5—H5C	109.5
N1—C1—N4	108.66 (11)	O1—C6—N6	122.10 (12)
N1—C1—N6	129.41 (11)	O1—C6—C7	122.90 (11)
N4—C1—N6	121.84 (11)	N6—C6—C7	115.00 (11)
O2—C2—N5	117.62 (12)	C6—C7—H7A	109.5
O2—C2—C3	124.49 (12)	C6—C7—H7B	109.5
N5—C2—C3	117.89 (11)	H7A—C7—H7B	109.5
C2—C3—H3A	109.5	C6—C7—H7C	109.5
C2—C3—H3B	109.5	H7A—C7—H7C	109.5
H3A—C3—H3B	109.5	H7B—C7—H7C	109.5
C1—N1—N2—N3	0.53 (14)	N5—N4—C1—N6	7.2 (2)
N1—N2—N3—N4	−0.89 (14)	C6—N6—C1—N1	−10.5 (2)
N2—N3—N4—C1	0.93 (13)	C6—N6—C1—N4	165.81 (11)
N2—N3—N4—N5	176.44 (11)	N4—N5—C2—O2	1.79 (17)
C1—N4—N5—C4	−96.01 (15)	C4—N5—C2—O2	−165.32 (12)
N3—N4—N5—C4	89.42 (14)	N4—N5—C2—C3	−177.37 (11)
C1—N4—N5—C2	95.54 (15)	C4—N5—C2—C3	15.51 (18)
N3—N4—N5—C2	−79.02 (14)	N4—N5—C4—O3	−175.90 (11)
N2—N1—C1—N4	0.09 (14)	C2—N5—C4—O3	−9.13 (19)
N2—N1—C1—N6	176.77 (12)	N4—N5—C4—C5	4.14 (15)
N3—N4—C1—N1	−0.63 (14)	C2—N5—C4—C5	170.91 (12)
N5—N4—C1—N1	−175.79 (11)	C1—N6—C6—O1	10.13 (19)
N3—N4—C1—N6	−177.61 (11)	C1—N6—C6—C7	−169.21 (11)

D—H···A	D—H	H···A	D···A	D—H···A
N6—H6N···O1i	0.902 (17)	1.955 (17)	2.7675 (16)	149.1 (14)
N6—H6N···N1i	0.902 (17)	2.473 (16)	3.1359 (18)	130.6 (13)
C3—H3A···O1ii	0.98	2.49	3.459 (2)	169
C7—H7C···O3iii	0.98	2.57	3.505 (2)	159

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N6—H6N⋯O1i	0.902 (17)	1.955 (17)	2.7675 (16)	149.1 (14)
N6—H6N⋯N1i	0.902 (17)	2.473 (16)	3.1359 (18)	130.6 (13)
C3—H3A⋯O1ii	0.98	2.49	3.459 (2)	169
C7—H7C⋯O3iii	0.98	2.57	3.505 (2)	159

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