Literature DB >> 21578490

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

Hui Zhang, Fang-Fang Jian.   

Abstract

The asymmetric unit of the title compound, C(3)H(5)N(5)O(2), contains three crystallograpically independent mol-ecules. In the crystal structure, inter-molecular N-H⋯N, N-H⋯O, O-H⋯N and O-H⋯O hydrogen bonds link the mol-ecules into a three-dimensional network.

Entities:  

Year:  2009        PMID： 21578490      PMCID： PMC2971256          DOI： 10.1107/S1600536809044432

Source DB:  PubMed          Journal:  Acta Crystallogr Sect E Struct Rep Online        ISSN： 1600-5368


Related literature

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

Experimental

Crystal data

C3H5N5O2 M = 143.12 Monoclinic, 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 ▶); cell refinement: SAINT (Bruker, 1997 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL. 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
C3H5N5O2F(000) = 888
Mr = 143.12Dx = 1.667 Mg m−3
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 mm−1
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
Bruker SMART CCD diffractometer2954 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.018
graphiteθmax = 27.5°, θmin = 3.2°
φ and ω scansh = −8→9
16421 measured reflectionsk = −15→15
3891 independent reflectionsl = −24→24
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 Å−3
0 restraintsΔρmin = −0.27 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.
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)
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)
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)
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
Table 1

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) ; (ii) ; (iii) ; (iv) ; (v) ; (vi) .

  1 in total

1.  A short history of SHELX.

Authors:  George M Sheldrick
Journal:  Acta Crystallogr A       Date:  2007-12-21       Impact factor: 2.290
  1 in total
  1 in total

1.  Crystal structure of poly[(μ3-4-amino-1,2,5-oxa-diazole-3-hydroxamato)thallium(I)].

Authors:  Inna S Safyanova; Oksana A Bondar; Anna V Pavlishchuk; Iryna V Omelchenko; Turganbay S Iskenderov; Valentina A Kalibabchuk
Journal:  Acta Crystallogr E Crystallogr Commun       Date:  2020-02-11
  1 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.