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Acta Crystallogr Sect E Struct Rep Online. 2009 November 1; 65(Pt 11): o2911.
Published online 2009 October 31. doi:  10.1107/S1600536809044432
PMCID: PMC2971256

(Z)-4-Amino-1,2,5-oxadiazole-3-carboxamide oxime

Abstract

The asymmetric unit of the title compound, C3H5N5O2, contains three crystallograpically independent mol­ecules. In the crystal structure, inter­molecular N—H(...)N, N—H(...)O, O—H(...)N and O—H(...)O hydrogen bonds link the mol­ecules into a three-dimensional network.

Related literature

For background to the biological activity of 1,2,5-oxadiazo­les, see: Renaud & Sebastian (2003 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-o2911-scheme1.jpg

Experimental

Crystal data

  • C3H5N5O2
  • M r = 143.12
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-o2911-efi1.jpg
  • a = 7.6514 (15) Å
  • b = 11.712 (2) Å
  • c = 19.218 (4) Å
  • β = 96.53 (3)°
  • V = 1710.9 (6) Å3
  • Z = 12
  • Mo Kα radiation
  • μ = 0.14 mm−1
  • T = 293 K
  • 0.20 × 0.15 × 0.10 mm

Data collection

  • Bruker SMART CCD diffractometer
  • Absorption correction: none
  • 16421 measured reflections
  • 3891 independent reflections
  • 2954 reflections with I > 2σ(I)
  • R int = 0.018

Refinement

  • R[F 2 > 2σ(F 2)] = 0.041
  • wR(F 2) = 0.131
  • S = 0.88
  • 3891 reflections
  • 271 parameters
  • H-atom parameters constrained
  • Δρmax = 0.41 e Å−3
  • Δρmin = −0.27 e Å−3

Data collection: SMART (Bruker, 1997 [triangle]); cell refinement: SAINT (Bruker, 1997 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXTL.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809044432/lh2924sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809044432/lh2924Isup2.hkl

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

supplementary crystallographic information

Comment

Furazanes (1,2,5-oxadiazoles )have been reported to exhibit a wide spectrum of biological properties (Renaud & Sebastian, 2003). In particular, agrochemical applications of furazanes and their derivatives such as, herbicides, plant-growth regulators and pesticides have been described. As part of our search for new non-linear optically active compounds we synthesized the title compound (I), and report its crystal structure herein. The asymmetric unit of (I) contains three crystallograpically independent molecules (see Fig. 1). In the crystal structure intermolecular N-H···N, N-H···O, O-H···N and O-H···O hydrogen bonds link molecules into a three-dimensional network.

Experimental

A mixture of propanedinitrile (0.1mol) hydroxylamine hydrochloride (0.22 mol) and 40% NaOH (10ml PH=10) was stirred in water (200mL) for 10h [diazo-reaction] to afford the title compound (yield 43%). Single crystals suitable for X-ray measurements were obtained by recrystallization from water and ethanol at room temperature.

Refinement

The H atoms were placed in calculated positions (N-H = 0.86; O-H = 0.82Å) and refined in a riding-motion approximation with Uiso(H) = 1.2Ueq(N,O).

Figures

Fig. 1.
The asymmetric unit of (I), drawn with 30% probability ellipsoids and spheres of arbritrary size for the H atoms.

Crystal data

C3H5N5O2F(000) = 888
Mr = 143.12Dx = 1.667 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 3891 reflections
a = 7.6514 (15) Åθ = 3.2–27.5°
b = 11.712 (2) ŵ = 0.14 mm1
c = 19.218 (4) ÅT = 293 K
β = 96.53 (3)°Bar, yellow
V = 1710.9 (6) Å30.20 × 0.15 × 0.10 mm
Z = 12

Data collection

Bruker SMART CCD diffractometer2954 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.018
graphiteθmax = 27.5°, θmin = 3.2°
[var phi] and ω scansh = −8→9
16421 measured reflectionsk = −15→15
3891 independent reflectionsl = −24→24

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)] = 0.041Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.131H-atom parameters constrained
S = 0.88w = 1/[σ2(Fo2) + (0.0979P)2 + 0.2809P] where P = (Fo2 + 2Fc2)/3
3891 reflections(Δ/σ)max < 0.001
271 parametersΔρmax = 0.41 e Å3
0 restraintsΔρmin = −0.27 e Å3

Special details

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.

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

xyzUiso*/Ueq
O2C0.33315 (11)0.21704 (8)0.19898 (5)0.0347 (2)
H2CA0.34660.26710.22890.042*
N4C0.50875 (13)0.20169 (9)0.18228 (5)0.0286 (2)
O1C0.87029 (12)0.05568 (9)0.03919 (5)0.0401 (3)
N2C0.69431 (13)0.05829 (9)0.04686 (6)0.0329 (3)
C3C0.50579 (14)0.14024 (9)0.12631 (6)0.0246 (3)
C2C0.67858 (15)0.11797 (9)0.10272 (6)0.0245 (3)
N5C0.36404 (14)0.09580 (10)0.08818 (6)0.0388 (3)
H5CA0.26080.10730.10040.047*
H5CB0.37650.05580.05150.047*
N1C0.89742 (14)0.21284 (9)0.19346 (5)0.0333 (3)
H1CA0.99800.24640.19750.040*
H1CB0.81220.25340.20560.040*
C1C0.85080 (14)0.15425 (10)0.13211 (6)0.0261 (3)
N3C0.96673 (14)0.11600 (10)0.09296 (6)0.0355 (3)
O2A0.32799 (11)0.39453 (7)0.29805 (4)0.0308 (2)
H20.30730.43900.26520.037*
N4A0.15351 (12)0.37447 (9)0.31574 (5)0.0275 (2)
C3A0.15895 (14)0.31171 (9)0.37121 (6)0.0230 (2)
O1A−0.21344 (12)0.22039 (9)0.45154 (5)0.0401 (3)
N5A0.30087 (14)0.26718 (10)0.40878 (6)0.0380 (3)
H5AA0.40390.27950.39660.046*
H5AB0.28890.22630.44510.046*
N2A−0.03621 (13)0.22429 (9)0.44691 (6)0.0318 (3)
N1A−0.22143 (14)0.38907 (10)0.30266 (6)0.0376 (3)
H1AA−0.32870.40430.28700.045*
H1AB−0.13700.41400.28090.045*
C2A−0.01584 (14)0.28737 (10)0.39297 (6)0.0249 (3)
C1A−0.18545 (15)0.32568 (10)0.36160 (6)0.0279 (3)
N3A−0.30561 (14)0.28438 (10)0.39787 (6)0.0377 (3)
O2B−0.00634 (11)0.55083 (8)0.19706 (5)0.0322 (2)
H2BA0.01380.59630.22940.039*
O1B0.52696 (12)0.37960 (9)0.03821 (5)0.0398 (3)
N4B0.16666 (12)0.52895 (9)0.17977 (5)0.0268 (2)
C3B0.16061 (14)0.47025 (9)0.12245 (6)0.0235 (2)
C2B0.33383 (14)0.44556 (9)0.09947 (6)0.0236 (2)
C1B0.50497 (14)0.48252 (10)0.12947 (6)0.0260 (3)
N1B0.54677 (14)0.54437 (10)0.18905 (6)0.0346 (3)
H1BA0.65510.55850.20350.042*
H1BB0.46480.56930.21220.042*
N5B0.01713 (13)0.43080 (10)0.08336 (6)0.0363 (3)
H5BA−0.08560.44390.09570.044*
H5BB0.02770.39240.04590.044*
N2B0.35054 (13)0.38407 (9)0.04455 (6)0.0328 (3)
N3B0.62218 (14)0.44196 (10)0.09165 (6)0.0353 (3)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O2C0.0275 (5)0.0428 (5)0.0354 (5)0.0058 (4)0.0103 (4)−0.0068 (4)
N4C0.0221 (5)0.0355 (5)0.0290 (5)0.0019 (4)0.0066 (4)−0.0024 (4)
O1C0.0256 (5)0.0562 (6)0.0402 (5)0.0016 (4)0.0112 (4)−0.0122 (4)
N2C0.0227 (5)0.0427 (6)0.0341 (6)−0.0002 (4)0.0074 (4)−0.0072 (5)
C3C0.0202 (5)0.0271 (5)0.0272 (6)0.0008 (4)0.0053 (4)0.0021 (4)
C2C0.0209 (6)0.0276 (5)0.0253 (6)0.0005 (4)0.0036 (4)0.0020 (4)
N5C0.0209 (5)0.0532 (7)0.0430 (7)−0.0033 (5)0.0069 (5)−0.0193 (5)
N1C0.0265 (5)0.0407 (6)0.0323 (6)−0.0065 (4)0.0016 (4)−0.0011 (4)
C1C0.0203 (6)0.0308 (6)0.0275 (6)−0.0001 (4)0.0039 (4)0.0056 (4)
N3C0.0244 (5)0.0470 (6)0.0358 (6)−0.0007 (4)0.0064 (4)−0.0026 (5)
O2A0.0260 (4)0.0395 (5)0.0282 (5)−0.0026 (3)0.0086 (3)0.0051 (4)
N4A0.0202 (5)0.0359 (5)0.0270 (5)−0.0001 (4)0.0048 (4)0.0034 (4)
C3A0.0192 (5)0.0264 (5)0.0237 (6)0.0007 (4)0.0039 (4)−0.0013 (4)
O1A0.0249 (5)0.0514 (6)0.0460 (6)−0.0017 (4)0.0132 (4)0.0107 (4)
N5A0.0189 (5)0.0557 (7)0.0397 (6)0.0051 (5)0.0049 (4)0.0211 (5)
N2A0.0225 (5)0.0391 (6)0.0349 (6)−0.0005 (4)0.0083 (4)0.0059 (4)
N1A0.0246 (5)0.0492 (7)0.0382 (6)0.0073 (5)−0.0004 (4)0.0059 (5)
C2A0.0198 (6)0.0286 (5)0.0263 (6)0.0009 (4)0.0037 (4)−0.0019 (4)
C1A0.0193 (6)0.0321 (6)0.0321 (6)0.0009 (4)0.0026 (5)−0.0054 (5)
N3A0.0216 (5)0.0469 (6)0.0451 (7)0.0012 (5)0.0066 (5)0.0017 (5)
O2B0.0227 (4)0.0439 (5)0.0307 (5)0.0038 (4)0.0067 (3)−0.0051 (4)
O1B0.0241 (5)0.0566 (6)0.0404 (5)0.0014 (4)0.0108 (4)−0.0122 (4)
N4B0.0195 (5)0.0359 (5)0.0254 (5)0.0014 (4)0.0050 (4)−0.0011 (4)
C3B0.0192 (5)0.0274 (5)0.0241 (6)−0.0001 (4)0.0033 (4)0.0034 (4)
C2B0.0204 (6)0.0274 (5)0.0233 (5)−0.0003 (4)0.0032 (4)0.0021 (4)
C1B0.0187 (5)0.0305 (6)0.0287 (6)−0.0013 (4)0.0028 (4)0.0050 (4)
N1B0.0258 (5)0.0437 (6)0.0332 (6)−0.0051 (4)−0.0012 (4)−0.0059 (5)
N5B0.0189 (5)0.0530 (7)0.0371 (6)−0.0025 (5)0.0036 (4)−0.0158 (5)
N2B0.0218 (5)0.0444 (6)0.0331 (6)−0.0007 (4)0.0072 (4)−0.0072 (5)
N3B0.0231 (5)0.0469 (6)0.0362 (6)−0.0013 (4)0.0053 (4)−0.0031 (5)

Geometric parameters (Å, °)

O2C—N4C1.4278 (12)N5A—H5AB0.8600
O2C—H2CA0.8200N2A—C2A1.2966 (15)
N4C—C3C1.2922 (15)N1A—C1A1.3560 (16)
O1C—N2C1.3715 (13)N1A—H1AA0.8600
O1C—N3C1.3921 (15)N1A—H1AB0.8600
N2C—C2C1.2979 (16)C2A—C1A1.4391 (16)
C3C—N5C1.3429 (15)C1A—N3A1.3080 (16)
C3C—C2C1.4690 (16)O2B—N4B1.4242 (12)
C2C—C1C1.4375 (16)O2B—H2BA0.8199
N5C—H5CA0.8600O1B—N2B1.3701 (13)
N5C—H5CB0.8600O1B—N3B1.3959 (15)
N1C—C1C1.3757 (16)N4B—C3B1.2949 (15)
N1C—H1CA0.8600C3B—N5B1.3399 (15)
N1C—H1CB0.8600C3B—C2B1.4725 (15)
C1C—N3C1.3059 (16)C2B—N2B1.2959 (15)
O2A—N4A1.4339 (12)C2B—C1B1.4361 (15)
O2A—H20.8199C1B—N3B1.3063 (15)
N4A—C3A1.2916 (15)C1B—N1B1.3620 (16)
C3A—N5A1.3394 (15)N1B—H1BA0.8600
C3A—C2A1.4738 (15)N1B—H1BB0.8600
O1A—N2A1.3698 (13)N5B—H5BA0.8600
O1A—N3A1.3990 (15)N5B—H5BB0.8600
N5A—H5AA0.8600
N4C—O2C—H2CA101.7C1A—N1A—H1AA120.0
C3C—N4C—O2C109.23 (10)C1A—N1A—H1AB120.0
N2C—O1C—N3C110.66 (9)H1AA—N1A—H1AB120.0
C2C—N2C—O1C106.59 (10)N2A—C2A—C1A109.14 (10)
N4C—C3C—N5C127.35 (11)N2A—C2A—C3A122.18 (10)
N4C—C3C—C2C115.13 (10)C1A—C2A—C3A128.68 (11)
N5C—C3C—C2C117.52 (11)N3A—C1A—N1A124.01 (11)
N2C—C2C—C1C108.48 (10)N3A—C1A—C2A108.45 (11)
N2C—C2C—C3C121.49 (11)N1A—C1A—C2A127.47 (11)
C1C—C2C—C3C130.03 (11)C1A—N3A—O1A105.37 (10)
C3C—N5C—H5CA120.0N4B—O2B—H2BA101.2
C3C—N5C—H5CB120.0N2B—O1B—N3B110.58 (9)
H5CA—N5C—H5CB120.0C3B—N4B—O2B110.48 (9)
C1C—N1C—H1CA116.6N4B—C3B—N5B127.43 (11)
C1C—N1C—H1CB112.2N4B—C3B—C2B114.40 (10)
H1CA—N1C—H1CB114.9N5B—C3B—C2B118.18 (10)
N3C—C1C—N1C122.54 (11)N2B—C2B—C1B108.93 (10)
N3C—C1C—C2C108.95 (11)N2B—C2B—C3B121.93 (10)
N1C—C1C—C2C128.38 (11)C1B—C2B—C3B129.13 (11)
C1C—N3C—O1C105.32 (10)N3B—C1B—N1B123.41 (11)
N4A—O2A—H2100.6N3B—C1B—C2B108.63 (11)
C3A—N4A—O2A110.21 (9)N1B—C1B—C2B127.88 (11)
N4A—C3A—N5A127.92 (11)C1B—N1B—H1BA120.0
N4A—C3A—C2A113.53 (10)C1B—N1B—H1BB120.0
N5A—C3A—C2A118.55 (10)H1BA—N1B—H1BB120.0
N2A—O1A—N3A110.73 (9)C3B—N5B—H5BA120.0
C3A—N5A—H5AA120.0C3B—N5B—H5BB120.0
C3A—N5A—H5AB120.0H5BA—N5B—H5BB120.0
H5AA—N5A—H5AB120.0C2B—N2B—O1B106.45 (10)
C2A—N2A—O1A106.31 (10)C1B—N3B—O1B105.40 (10)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O2C—H2CA···O2A0.822.012.8222 (14)169
O2A—H2···N4B0.822.142.9208 (14)160
N5C—H5CA···N3Ci0.862.243.0610 (17)160
N5C—H5CB···N2Cii0.862.333.1508 (17)160
N1C—H1CA···O2Ciii0.862.583.3239 (15)145
N1C—H1CB···N1Aiii0.862.493.1504 (17)135
N1C—H1CB···N4C0.862.392.9600 (16)124
N5A—H5AA···N3Aiii0.862.223.0486 (17)162
N5A—H5AB···N2Biv0.862.313.1409 (17)162
N1A—H1AA···N1Bi0.862.603.2156 (17)130
N1A—H1AB···O2B0.862.563.3430 (17)153
N1A—H1AB···N4A0.862.292.8563 (15)123
O2B—H2BA···N1Cv0.822.072.8849 (15)171
N1B—H1BB···N4B0.862.342.8992 (15)123
N1B—H1BB···N4Cv0.862.543.1510 (17)129
N5B—H5BA···N3Bi0.862.233.0470 (16)159
N5B—H5BB···N2Avi0.862.353.1779 (17)162

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: LH2924).

References

  • Bruker (1997). SMART and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Renaud, B. & Sebastian, W. (2003). Heterocycles, 60, 2417–2424.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]

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