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Acta Crystallogr Sect E Struct Rep Online. 2009 August 1; 65(Pt 8): o1902.
Published online 2009 July 18. doi:  10.1107/S1600536809027421
PMCID: PMC2977091

N-(1-Diacetyl­amino-1H-tetra­zol-5-yl)acetamide

Abstract

In the crystal structure of the title compound, C7H10N6O3, there are N—H(...)O, N—H(...)N and C—H(...)O inter­actions, generating a three-dimensional supra­molecular 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 [triangle]). 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 [triangle]). For hydrogen-bond-length data, see: Desiraju & Steiner (1999 [triangle]). For carbon­yl–carbonyl inter­actions, see: Allen et al. (1998 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-o1902-scheme1.jpg

Experimental

Crystal data

  • C7H10N6O3
  • M r = 226.21
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-o1902-efi1.jpg
  • 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 [triangle]); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: ORTEP-3 (Farrugia, 1997 [triangle]); software used to prepare material for publication: WinGX (Farrugia, 1999 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

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

Acknowledgments

This work was supported financially by the State Key Laboratory of Explosion Science and Technology, Beijing Institute of Technology, China (No. ZDKT08–01).

supplementary crystallographic information

Comment

1, 5-Diaminotetrazole has been reported using as a valuable intermediate in preparation of tetrazole-containing compounds which might have prospective application in energetic materials (Gaponnik & Karavai, 1984; Galvez-Ruiz et al., 2005). The presence of three acetyl groups in the title compound may put itself as an intermediate for preparing derivatives which have a bigger molecule. The title compound had been prepared by Gaponnik & Karavai (1984). Herein we report its crystal structure.

The molecular structure of the title compound is presented in Fig. 1, the bond distances and bond angles in the title compound are as expected for a molecule of this kind. The molecules are linked to each other via N—H···O, N—H···N and C—H···O hydrogen bonds (Table 1). The range for the H···O distances agree with those found for weak C—H···O hydrogen bonds (Desiraju & Steiner, 1999). The O1···C4ii distance is 2.8994 (18) Å [symmetry code: (ii) x, 3/2-y, -1/2+z], this distance agrees with the disscusion of intermolecular C=O ···C=O interactions (Allen et al., 1998), which may contribute to the stabilization of crystal structure.

Experimental

The title compound was prepared according to the literature method (Gaponnik & Karavai, 1984). 220 mg of obtained product was dissolved in the mixture solution of methanol (10 ml) and acetone (20 ml) and the solution was kept at room temperature to give suitable crystals for X-ray structure determination.

Refinement

Amino H atoms were located in a difference Fourier maps and were refined isotropically. Methyl H-atoms were placed in calculated positions with C—H = 0.98 Å, and torsion angles were refined to fit the electron density with Uiso(H) = 1.2Ueq(C).

Figures

Fig. 1.
The molecular structure of the title compound with the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.

Crystal data

C7H10N6O3F(000) = 472
Mr = 226.21Dx = 1.523 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 3214 reflections
a = 6.973 (2) Åθ = 3.1–27.5°
b = 16.678 (5) ŵ = 0.12 mm1
c = 8.871 (3) ÅT = 93 K
β = 106.987 (4)°Block, colourless
V = 986.6 (5) Å30.60 × 0.25 × 0.18 mm
Z = 4

Data collection

Rigaku Saturn724+ diffractometer1898 reflections with I > 2σ(I)
Radiation source: Rotating AnodeRint = 0.028
graphiteθmax = 27.5°, θmin = 3.1°
Detector resolution: 28.5714 pixels mm-1h = −9→8
Multi–scank = −21→20
7848 measured reflectionsl = −11→11
2255 independent reflections

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.037Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.089H atoms treated by a mixture of independent and constrained refinement
S = 1.00w = 1/[σ2(Fo2) + (0.046P)2 + 0.18P] where P = (Fo2 + 2Fc2)/3
2255 reflections(Δ/σ)max < 0.001
152 parametersΔρmax = 0.27 e Å3
0 restraintsΔρmin = −0.31 e Å3

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/Ueq
O10.98846 (13)0.79462 (5)0.37140 (10)0.0163 (2)
O20.33700 (14)0.66238 (7)0.56926 (11)0.0280 (3)
O30.77881 (14)0.53886 (6)0.89046 (10)0.0199 (2)
N10.71476 (16)0.66802 (7)0.30010 (12)0.0170 (2)
N20.60145 (16)0.59851 (7)0.26310 (12)0.0182 (3)
N30.56513 (16)0.56773 (6)0.38460 (12)0.0170 (2)
N40.65849 (16)0.61680 (6)0.50781 (12)0.0141 (2)
N50.64409 (15)0.60537 (6)0.65826 (12)0.0137 (2)
N60.85854 (15)0.73478 (6)0.55048 (12)0.0147 (2)
C10.74742 (18)0.67770 (7)0.45264 (14)0.0133 (3)
C20.46012 (19)0.63385 (8)0.68129 (15)0.0176 (3)
C30.4357 (2)0.62716 (9)0.84238 (15)0.0216 (3)
H3A0.31490.65620.84590.026*
H3B0.55310.65040.91950.026*
H3C0.42320.57050.86760.026*
C40.79059 (19)0.55442 (7)0.76155 (15)0.0153 (3)
C50.9522 (2)0.52400 (8)0.69584 (16)0.0206 (3)
H5A1.05700.49780.77980.025*
H5B1.01040.56900.65320.025*
H5C0.89490.48530.61160.025*
C60.98590 (18)0.78772 (7)0.50729 (14)0.0132 (3)
C71.1204 (2)0.83460 (8)0.63980 (15)0.0186 (3)
H7A1.24880.80660.67990.022*
H7B1.05720.84010.72450.022*
H7C1.14330.88790.60190.022*
H6N0.858 (2)0.7348 (10)0.652 (2)0.034 (5)*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O10.0204 (5)0.0177 (5)0.0116 (4)−0.0020 (4)0.0057 (4)0.0007 (4)
O20.0230 (5)0.0397 (6)0.0199 (5)0.0122 (5)0.0039 (4)0.0046 (4)
O30.0220 (5)0.0225 (5)0.0150 (5)0.0013 (4)0.0051 (4)0.0037 (4)
N10.0176 (6)0.0200 (6)0.0128 (5)−0.0040 (4)0.0037 (4)−0.0021 (4)
N20.0191 (6)0.0203 (6)0.0148 (5)−0.0039 (4)0.0044 (4)−0.0020 (4)
N30.0186 (6)0.0177 (6)0.0139 (5)−0.0034 (4)0.0034 (4)−0.0026 (4)
N40.0172 (5)0.0152 (5)0.0099 (5)−0.0029 (4)0.0040 (4)−0.0007 (4)
N50.0151 (5)0.0161 (5)0.0106 (5)−0.0005 (4)0.0049 (4)0.0016 (4)
N60.0181 (5)0.0169 (6)0.0099 (5)−0.0042 (4)0.0051 (4)−0.0015 (4)
C10.0130 (6)0.0143 (6)0.0130 (6)0.0000 (5)0.0043 (5)0.0011 (5)
C20.0167 (7)0.0192 (7)0.0170 (6)−0.0001 (5)0.0051 (5)−0.0007 (5)
C30.0183 (7)0.0295 (8)0.0187 (7)0.0018 (5)0.0083 (6)−0.0004 (6)
C40.0152 (7)0.0130 (6)0.0160 (6)−0.0024 (5)0.0021 (5)−0.0005 (5)
C50.0185 (7)0.0217 (7)0.0228 (7)0.0031 (5)0.0079 (6)0.0018 (6)
C60.0142 (6)0.0133 (6)0.0125 (6)0.0022 (5)0.0045 (5)0.0016 (5)
C70.0218 (7)0.0182 (7)0.0154 (6)−0.0047 (5)0.0048 (5)−0.0027 (5)

Geometric parameters (Å, °)

O1—C61.2164 (15)N6—H6N0.900 (16)
O2—C21.2052 (16)C2—C31.4919 (18)
O3—C41.1987 (15)C3—H3A0.9800
N1—C11.3149 (16)C3—H3B0.9800
N1—N21.3871 (15)C3—H3C0.9800
N2—N31.2841 (15)C4—C51.5004 (18)
N3—N41.3684 (15)C5—H5A0.9800
N4—C11.3538 (16)C5—H5B0.9800
N4—N51.3806 (14)C5—H5C0.9800
N5—C41.4346 (16)C6—C71.4927 (17)
N5—C21.4374 (16)C7—H7A0.9800
N6—C11.3663 (16)C7—H7B0.9800
N6—C61.3834 (16)C7—H7C0.9800
C1—N1—N2105.16 (10)C2—C3—H3C109.5
N3—N2—N1111.96 (10)H3A—C3—H3C109.5
N2—N3—N4105.48 (10)H3B—C3—H3C109.5
C1—N4—N3108.73 (10)O3—C4—N5120.21 (12)
C1—N4—N5128.57 (10)O3—C4—C5124.47 (12)
N3—N4—N5122.52 (10)N5—C4—C5115.32 (11)
N4—N5—C4117.38 (10)C4—C5—H5A109.5
N4—N5—C2114.32 (10)C4—C5—H5B109.5
C4—N5—C2127.12 (10)H5A—C5—H5B109.5
C1—N6—C6124.02 (11)C4—C5—H5C109.5
C1—N6—H6N117.8 (11)H5A—C5—H5C109.5
C6—N6—H6N117.9 (11)H5B—C5—H5C109.5
N1—C1—N4108.66 (11)O1—C6—N6122.10 (12)
N1—C1—N6129.41 (11)O1—C6—C7122.90 (11)
N4—C1—N6121.84 (11)N6—C6—C7115.00 (11)
O2—C2—N5117.62 (12)C6—C7—H7A109.5
O2—C2—C3124.49 (12)C6—C7—H7B109.5
N5—C2—C3117.89 (11)H7A—C7—H7B109.5
C2—C3—H3A109.5C6—C7—H7C109.5
C2—C3—H3B109.5H7A—C7—H7C109.5
H3A—C3—H3B109.5H7B—C7—H7C109.5
C1—N1—N2—N30.53 (14)N5—N4—C1—N67.2 (2)
N1—N2—N3—N4−0.89 (14)C6—N6—C1—N1−10.5 (2)
N2—N3—N4—C10.93 (13)C6—N6—C1—N4165.81 (11)
N2—N3—N4—N5176.44 (11)N4—N5—C2—O21.79 (17)
C1—N4—N5—C4−96.01 (15)C4—N5—C2—O2−165.32 (12)
N3—N4—N5—C489.42 (14)N4—N5—C2—C3−177.37 (11)
C1—N4—N5—C295.54 (15)C4—N5—C2—C315.51 (18)
N3—N4—N5—C2−79.02 (14)N4—N5—C4—O3−175.90 (11)
N2—N1—C1—N40.09 (14)C2—N5—C4—O3−9.13 (19)
N2—N1—C1—N6176.77 (12)N4—N5—C4—C54.14 (15)
N3—N4—C1—N1−0.63 (14)C2—N5—C4—C5170.91 (12)
N5—N4—C1—N1−175.79 (11)C1—N6—C6—O110.13 (19)
N3—N4—C1—N6−177.61 (11)C1—N6—C6—C7−169.21 (11)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N6—H6N···O1i0.902 (17)1.955 (17)2.7675 (16)149.1 (14)
N6—H6N···N1i0.902 (17)2.473 (16)3.1359 (18)130.6 (13)
C3—H3A···O1ii0.982.493.459 (2)169
C7—H7C···O3iii0.982.573.505 (2)159

Symmetry codes: (i) x, −y+3/2, z+1/2; (ii) x−1, −y+3/2, z+1/2; (iii) −x+2, y+1/2, −z+3/2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: XU2550).

References

  • Allen, F. H., Baalham, C. A., Lommerse, J. P. M. & Raithby, P. R. (1998). Acta Cryst. B54, 320–329.
  • Desiraju, G. & Steiner, T. (1999). In The Weak Hydrogen Bond: Applications to Structural Chemistry and Biology New York: Oxford University Press.
  • Farrugia, L. J. (1997). J. Appl. Cryst.30, 565.
  • Farrugia, L. J. (1999). J. Appl. Cryst.32, 837–838.
  • Galvez-Ruiz, J. C., Holl, G., Karaghiosoff, K., Klapötke, T. M., Lohnwitz, K., Mayer, P., Noth, H., Polborn, K., Rohbogner, C. J., Suter, M. & Weigand, J. J. (2005). Inorg. Chem 44, 4237–4253. [PubMed]
  • Gaponnik, P. N. & Karavai, V. P. (1984). Khim. Geterotsikl. Soedin 12, 1683–1686.
  • Rigaku (2008). CrystalClear Rigaku Corporation, Tokyo, Japan.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]

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