There is one independent molecule in the asymmetric unit of the title compound (alternatively named
N-hydroxyacetamide), C
2H
5NO
2. It crystallizes in the noncentrosymmetric space group
P4
3. 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), B
26, 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
CCDC reference: 1576592
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (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
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).
Crystal data top
C2H5NO2 | Dx = 1.318 Mg m−3 |
Mr = 75.07 | Mo Kα radiation, λ = 0.71073 Å |
Tetragonal, P41 | Cell parameters from 2579 reflections |
a = 5.2344 (6) Å | θ = 3.9–26.0° |
c = 13.809 (2) Å | µ = 0.12 mm−1 |
V = 378.34 (10) Å3 | T = 293 K |
Z = 4 | Plate, colourless |
F(000) = 160 | 0.05 × 0.04 × 0.03 mm |
Data collection top
Xcalibur diffractometer | 683 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.018 |
Detector resolution: 1024 pixels mm-1 | θmax = 26.0°, θmin = 3.9° |
ω–scan | h = −5→6 |
2579 measured reflections | k = −6→5 |
751 independent reflections | l = −16→16 |
Refinement top
Refinement on F2 | H-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) = 0.086 | Δρmax = 0.10 e Å−3 |
S = 1.11 | Δρmin = −0.14 e Å−3 |
751 reflections | Extinction correction: SHELXL2014 (Sheldrick, 2015b), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
47 parameters | Extinction coefficient: 0.24 (4) |
1 restraint | Absolute structure: Flack x determined using 307 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons et al., 2013) |
Hydrogen site location: inferred from neighbouring sites | Absolute 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 | x | y | z | Uiso*/Ueq | |
C1 | 0.4274 (4) | 0.0253 (4) | 0.41879 (16) | 0.0485 (5) | |
C2 | 0.6056 (5) | 0.2400 (5) | 0.4372 (2) | 0.0672 (7) | |
H1 | 0.5655 | 0.3173 | 0.4984 | 0.101* | |
H2 | 0.7778 | 0.1769 | 0.4385 | 0.101* | |
H3 | 0.5888 | 0.3647 | 0.3867 | 0.101* | |
N1 | 0.2554 (4) | −0.0170 (4) | 0.48604 (13) | 0.0600 (6) | |
H4 | 0.2639 | 0.0612 | 0.5407 | 0.072* | |
O1 | 0.0601 (3) | −0.1893 (3) | 0.46796 (13) | 0.0663 (5) | |
H5 | 0.0673 | −0.3064 | 0.5073 | 0.099* | |
O2 | 0.4385 (3) | −0.1073 (3) | 0.34398 (11) | 0.0584 (5) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.0516 (12) | 0.0508 (11) | 0.0430 (10) | 0.0120 (9) | −0.0098 (9) | −0.0019 (8) |
C2 | 0.0614 (14) | 0.0644 (15) | 0.0759 (18) | −0.0010 (12) | −0.0132 (12) | −0.0134 (12) |
N1 | 0.0744 (13) | 0.0623 (10) | 0.0433 (10) | −0.0005 (10) | 0.0010 (9) | −0.0117 (8) |
O1 | 0.0715 (11) | 0.0685 (9) | 0.0589 (10) | −0.0048 (9) | 0.0023 (9) | 0.0067 (8) |
O2 | 0.0595 (10) | 0.0706 (11) | 0.0451 (9) | −0.0034 (7) | −0.0005 (6) | −0.0134 (7) |
Geometric parameters (Å, º) top
C1—O2 | 1.246 (3) | C2—H3 | 0.9600 |
C1—N1 | 1.312 (3) | N1—O1 | 1.386 (3) |
C1—C2 | 1.482 (4) | N1—H4 | 0.8600 |
C2—H1 | 0.9600 | O1—H5 | 0.8200 |
C2—H2 | 0.9600 | | |
| | | |
O2—C1—N1 | 121.6 (2) | H1—C2—H3 | 109.5 |
O2—C1—C2 | 122.4 (2) | H2—C2—H3 | 109.5 |
N1—C1—C2 | 116.0 (2) | C1—N1—O1 | 119.24 (17) |
C1—C2—H1 | 109.5 | C1—N1—H4 | 120.4 |
C1—C2—H2 | 109.5 | O1—N1—H4 | 120.4 |
H1—C2—H2 | 109.5 | N1—O1—H5 | 109.5 |
C1—C2—H3 | 109.5 | | |
| | | |
O2—C1—N1—O1 | −9.0 (3) | C2—C1—N1—O1 | 170.80 (19) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C2—H2···O1i | 0.96 | 2.45 | 3.300 (3) | 147 |
N1—H4···O1ii | 0.86 | 2.48 | 3.246 (3) | 149 |
N1—H4···O2ii | 0.86 | 2.26 | 2.917 (3) | 133 |
O1—H5···O2iii | 0.82 | 1.81 | 2.624 (2) | 176 |
Symmetry codes: (i) x+1, y, z; (ii) −y, x, z+1/4; (iii) −y, x−1, z+1/4. |