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There is one independent mol­ecule in the asymmetric unit of the title compound (alternatively named N-hy­droxy­acetamide), C2H5NO2. It crystallizes in the noncentrosymmetric space group P43. The structure is an anhydrous form of acetyl­hydroxamic acid with typical geometry that corresponds well with the hydrated structure described by Bracher & Small [Acta Cryst. (1970), B26, 1705–1709]. In the crystal, N—H...O and O—H...O hydrogen bonds connect the mol­ecules into chains in the c-axis direction.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2414314617013906/bt4064sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2414314617013906/bt4064Isup2.hkl
Contains datablock I

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2414314617013906/bt4064Isup3.cml
Supplementary material

CCDC reference: 1576592

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.028
  • wR factor = 0.086
  • Data-to-parameter ratio = 16.0

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT978_ALERT_2_C Number C-C Bonds with Positive Residual Density. 0 Info
Alert level G PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms .............. 2 Report PLAT032_ALERT_4_G Std. Uncertainty on Flack Parameter Value High . 0.400 Report PLAT199_ALERT_1_G Reported _cell_measurement_temperature ..... (K) 293 Check PLAT200_ALERT_1_G Reported _diffrn_ambient_temperature ..... (K) 293 Check PLAT380_ALERT_4_G Incorrectly? Oriented X(sp2)-Methyl Moiety ..... C2 Check PLAT850_ALERT_4_G Check Flack Parameter Exact Value 0.00 and s.u. 0.40 Check
0 ALERT level A = Most likely a serious problem - resolve or explain 0 ALERT level B = A potentially serious problem, consider carefully 1 ALERT level C = Check. Ensure it is not caused by an omission or oversight 6 ALERT level G = General information/check it is not something unexpected 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 3 ALERT type 4 Improvement, methodology, query or suggestion 1 ALERT type 5 Informative message, check

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2008); cell refinement: CrysAlis CCD (Oxford Diffraction, 2008); data reduction: CrysAlis CCD (Oxford Diffraction, 2008); program(s) used to solve structure: SHELXS2014 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL2014 (Sheldrick, 2015b).

N-Hydroxyacetamide top
Crystal data top
C2H5NO2Dx = 1.318 Mg m3
Mr = 75.07Mo Kα radiation, λ = 0.71073 Å
Tetragonal, P41Cell parameters from 2579 reflections
a = 5.2344 (6) Åθ = 3.9–26.0°
c = 13.809 (2) ŵ = 0.12 mm1
V = 378.34 (10) Å3T = 293 K
Z = 4Plate, colourless
F(000) = 1600.05 × 0.04 × 0.03 mm
Data collection top
Xcalibur
diffractometer
683 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.018
Detector resolution: 1024 pixels mm-1θmax = 26.0°, θmin = 3.9°
ω–scanh = 56
2579 measured reflectionsk = 65
751 independent reflectionsl = 1616
Refinement top
Refinement on F2H-atom parameters constrained
Least-squares matrix: full w = 1/[σ2(Fo2) + (0.0584P)2 + 0.0038P]
where P = (Fo2 + 2Fc2)/3
R[F2 > 2σ(F2)] = 0.028(Δ/σ)max < 0.001
wR(F2) = 0.086Δρmax = 0.10 e Å3
S = 1.11Δρmin = 0.14 e Å3
751 reflectionsExtinction correction: SHELXL2014 (Sheldrick, 2015b), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
47 parametersExtinction coefficient: 0.24 (4)
1 restraintAbsolute structure: Flack x determined using 307 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
Hydrogen site location: inferred from neighbouring sitesAbsolute structure parameter: 0.0 (4)
Special details top

Geometry. All esds (except the esd in the dihedral angle between 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.4274 (4)0.0253 (4)0.41879 (16)0.0485 (5)
C20.6056 (5)0.2400 (5)0.4372 (2)0.0672 (7)
H10.56550.31730.49840.101*
H20.77780.17690.43850.101*
H30.58880.36470.38670.101*
N10.2554 (4)0.0170 (4)0.48604 (13)0.0600 (6)
H40.26390.06120.54070.072*
O10.0601 (3)0.1893 (3)0.46796 (13)0.0663 (5)
H50.06730.30640.50730.099*
O20.4385 (3)0.1073 (3)0.34398 (11)0.0584 (5)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0516 (12)0.0508 (11)0.0430 (10)0.0120 (9)0.0098 (9)0.0019 (8)
C20.0614 (14)0.0644 (15)0.0759 (18)0.0010 (12)0.0132 (12)0.0134 (12)
N10.0744 (13)0.0623 (10)0.0433 (10)0.0005 (10)0.0010 (9)0.0117 (8)
O10.0715 (11)0.0685 (9)0.0589 (10)0.0048 (9)0.0023 (9)0.0067 (8)
O20.0595 (10)0.0706 (11)0.0451 (9)0.0034 (7)0.0005 (6)0.0134 (7)
Geometric parameters (Å, º) top
C1—O21.246 (3)C2—H30.9600
C1—N11.312 (3)N1—O11.386 (3)
C1—C21.482 (4)N1—H40.8600
C2—H10.9600O1—H50.8200
C2—H20.9600
O2—C1—N1121.6 (2)H1—C2—H3109.5
O2—C1—C2122.4 (2)H2—C2—H3109.5
N1—C1—C2116.0 (2)C1—N1—O1119.24 (17)
C1—C2—H1109.5C1—N1—H4120.4
C1—C2—H2109.5O1—N1—H4120.4
H1—C2—H2109.5N1—O1—H5109.5
C1—C2—H3109.5
O2—C1—N1—O19.0 (3)C2—C1—N1—O1170.80 (19)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C2—H2···O1i0.962.453.300 (3)147
N1—H4···O1ii0.862.483.246 (3)149
N1—H4···O2ii0.862.262.917 (3)133
O1—H5···O2iii0.821.812.624 (2)176
Symmetry codes: (i) x+1, y, z; (ii) y, x, z+1/4; (iii) y, x1, z+1/4.
 

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