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

He, C.-L.; Du, Z.-M.; Tang, Z.-Q.; Cong, X.-M.; Meng, L.-Q.

doi:10.1107/S1600536809027421

organic compounds

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Volume 65| Part 8| August 2009| Page o1902

doi:10.1107/S1600536809027421

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

Chun-Lin He,^a Zhi-Ming Du,^a ^* Zheng-Qiang Tang,^a Xiao-Min Cong ^a and Ling-Qiao Meng ^a

^aState Key Laboratory of Explosion Science and Technology, Beijing Institute of Technology, Beijing 100081, People's Republic of China
^*Correspondence e-mail: duzhiming430@sohu.com

(Received 6 July 2009; accepted 13 July 2009; online 18 July 2009)

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 ). 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_r = 226.21
Monoclinic, P 2₁ /c
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[F² > 2σ(F²)] = 0.037
wR(F²) = 0.089
S = 1.00
2255 reflections
152 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.27 e Å⁻³
Δρ_min = −0.31 e Å⁻³

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) $[x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ ; (ii) $[x-1, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ ; (iii) $[-x+2, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

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 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809027421/xu2550sup1.cif

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

checkCIF report

Comment top

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.

Related literature top

For the preparation, see: Gaponnik & Karavai (1984). For general background, 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 top

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.

Computing details top

Data collection: CrystalClear (Rigaku, 2008); cell refinement: CrystalClear (Rigaku, 2008); data reduction: CrystalClear (Rigaku, 2008); 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).

Figures top

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

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

Crystal data top

C₇H₁₀N₆O₃	F(000) = 472
M_r = 226.21	D_x = 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

Data collection top

Rigaku Saturn724+ diffractometer	1898 reflections with I > 2σ(I)
Radiation source: Rotating Anode	R_int = 0.028
Graphite monochromator	θ_max = 27.5°, θ_min = 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 top

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(F_o²) + (0.046P)² + 0.18P] where P = (F_o² + 2F_c²)/3
2255 reflections	(Δ/σ)_max < 0.001
152 parameters	Δρ_max = 0.27 e Å⁻³
0 restraints	Δρ_min = −0.31 e Å⁻³

Crystal data top

C₇H₁₀N₆O₃	V = 986.6 (5) Å³
M_r = 226.21	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 6.973 (2) Å	µ = 0.12 mm⁻¹
b = 16.678 (5) Å	T = 93 K
c = 8.871 (3) Å	0.60 × 0.25 × 0.18 mm
β = 106.987 (4)°

Data collection top

Rigaku Saturn724+ diffractometer	1898 reflections with I > 2σ(I)
7848 measured reflections	R_int = 0.028
2255 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.037	0 restraints
wR(F²) = 0.089	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	Δρ_max = 0.27 e Å⁻³
2255 reflections	Δρ_min = −0.31 e Å⁻³
152 parameters

Special details top

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) top

	x	y	z	U_iso*/U_eq
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)*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) 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.

Experimental details

Crystal data
Chemical formula	C₇H₁₀N₆O₃
M_r	226.21
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	93
a, b, c (Å)	6.973 (2), 16.678 (5), 8.871 (3)
β (°)	106.987 (4)
V (Å³)	986.6 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.12
Crystal size (mm)	0.60 × 0.25 × 0.18

Data collection
Diffractometer	Rigaku Saturn724+ diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	7848, 2255, 1898
R_int	0.028
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.037, 0.089, 1.00
No. of reflections	2255
No. of parameters	152
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.27, −0.31

Computer programs: CrystalClear (Rigaku, 2008), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top

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	2.4900	3.459 (2)	169.00
C7—H7C···O3ⁱⁱⁱ	0.98	2.5700	3.505 (2)	159.00

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.

Acknowledgements

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

References

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