Download citation
Download citation
link to html
The title compound, N-hydroxy­propan­amide, C3H7NO2, crystallizes with Z' = 3 in P21/c. The mol­ecules are linked by three N-H...O hydrogen bonds [N...O 2.8012 (16) to 2.8958 (15) Å; N-H...O 163 to 168°] and by three O-H...O hydrogen bonds [O...O 2.6589 (15) to 2.6775 (17) Å; O-H...O 165 to 177°] into a single three-dimensional framework.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270101000075/sk1449sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270101000075/sk1449Isup2.hkl
Contains datablock I

CCDC reference: 163927

Computing details top

Data collection: CAD4 (Nonius, 1992); cell refinement: SET4 and CELDIM (Nonius, 1992); data reduction: HELENA in PLATON (Spek 2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2000); software used to prepare material for publication: SHELXL97.

N-propionylhydroxylamine top
Crystal data top
C3H7NO2F(000) = 576
Mr = 89.10Dx = 1.282 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 12.052 (3) ÅCell parameters from 25 reflections
b = 8.009 (3) Åθ = 9.8–11.2°
c = 14.354 (3) ŵ = 0.11 mm1
β = 92.35 (2)°T = 293 K
V = 1384.3 (7) Å3Block, colourless
Z = 120.40 × 0.40 × 0.40 mm
Data collection top
Nonius CAD4
diffractometer
Rint = 0.017
Radiation source: fine-focus sealed X-ray tubeθmax = 27.0°, θmin = 2.8°
Graphite monochromatorh = 015
θ/2θ scansk = 010
3374 measured reflectionsl = 1818
3016 independent reflections3 standard reflections every 120 min
2426 reflections with I > 2σ(I) intensity decay: none
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.038H-atom parameters constrained
wR(F2) = 0.114 w = 1/[σ2(Fo2) + (0.0591P)2 + 0.3743P]
where P = (Fo2 + 2Fc2)/3
S = 1.02(Δ/σ)max < 0.001
3016 reflectionsΔρmax = 0.19 e Å3
170 parametersΔρmin = 0.28 e Å3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.026 (3)
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O110.16302 (8)0.37086 (14)0.32034 (9)0.0536 (3)
O120.12245 (8)0.05820 (13)0.37449 (7)0.0456 (3)
N10.04621 (8)0.18708 (15)0.38178 (8)0.0372 (3)
C110.07007 (10)0.33463 (17)0.34863 (9)0.0348 (3)
C120.02402 (11)0.45828 (19)0.34589 (11)0.0433 (3)
C130.00887 (14)0.6290 (2)0.38140 (13)0.0562 (4)
O210.15986 (7)0.57334 (15)0.04293 (7)0.0483 (3)
O220.20525 (8)0.64442 (13)0.22256 (7)0.0427 (3)
N20.28637 (8)0.60463 (15)0.16042 (8)0.0376 (3)
C210.25830 (10)0.57854 (17)0.07233 (9)0.0351 (3)
C220.35365 (11)0.5567 (2)0.00888 (10)0.0462 (4)
C230.35481 (16)0.6881 (3)0.06606 (13)0.0671 (5)
O310.50451 (8)0.08237 (15)0.23862 (8)0.0496 (3)
O320.45586 (9)0.31530 (15)0.36718 (8)0.0503 (3)
N30.37691 (9)0.23735 (16)0.30936 (9)0.0423 (3)
C310.40608 (10)0.12399 (17)0.24912 (10)0.0375 (3)
C320.31184 (12)0.0503 (2)0.19124 (12)0.0491 (4)
C330.31564 (16)0.0997 (3)0.09140 (14)0.0723 (6)
H120.13220.01280.42540.068*
H10.01590.17030.40770.045*
H12A0.08310.41550.38310.052*
H12B0.05310.46850.28210.052*
H13A0.04320.61920.44270.084*
H13B0.05600.69820.38390.084*
H13C0.06040.67840.34020.084*
H220.19020.56140.25300.064*
H20.35470.59710.17950.045*
H22A0.34860.44730.02000.055*
H22B0.42290.56150.04560.055*
H23A0.28640.68380.10270.101*
H23B0.41590.66810.10540.101*
H23C0.36280.79630.03780.101*
H320.47500.40310.34320.075*
H30.30800.26360.31300.051*
H32A0.31490.07050.19590.059*
H32B0.24200.08690.21570.059*
H33A0.30360.21790.08570.108*
H33B0.25880.04130.05580.108*
H33C0.38700.07200.06830.108*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O110.0317 (5)0.0521 (6)0.0784 (8)0.0049 (4)0.0193 (5)0.0184 (6)
O120.0445 (5)0.0481 (6)0.0446 (5)0.0145 (4)0.0054 (4)0.0095 (4)
N10.0256 (5)0.0436 (6)0.0427 (6)0.0034 (4)0.0056 (4)0.0060 (5)
C110.0255 (6)0.0445 (7)0.0345 (6)0.0023 (5)0.0024 (5)0.0034 (5)
C120.0312 (6)0.0484 (8)0.0502 (8)0.0074 (6)0.0018 (6)0.0044 (6)
C130.0560 (9)0.0511 (9)0.0624 (10)0.0063 (7)0.0140 (8)0.0039 (8)
O210.0266 (5)0.0720 (7)0.0463 (6)0.0015 (4)0.0008 (4)0.0150 (5)
O220.0426 (5)0.0453 (6)0.0413 (5)0.0016 (4)0.0134 (4)0.0008 (4)
N20.0255 (5)0.0491 (7)0.0383 (6)0.0012 (5)0.0028 (4)0.0006 (5)
C210.0262 (6)0.0381 (7)0.0411 (7)0.0012 (5)0.0030 (5)0.0038 (5)
C220.0309 (6)0.0637 (10)0.0446 (8)0.0037 (6)0.0078 (6)0.0067 (7)
C230.0664 (11)0.0741 (12)0.0622 (11)0.0079 (9)0.0219 (9)0.0051 (9)
O310.0274 (5)0.0599 (7)0.0614 (7)0.0068 (4)0.0002 (4)0.0054 (5)
O320.0449 (6)0.0546 (7)0.0509 (6)0.0078 (5)0.0063 (5)0.0010 (5)
N30.0250 (5)0.0468 (7)0.0553 (7)0.0010 (5)0.0015 (5)0.0017 (6)
C310.0259 (6)0.0384 (7)0.0482 (7)0.0013 (5)0.0022 (5)0.0084 (6)
C320.0329 (7)0.0487 (8)0.0654 (10)0.0083 (6)0.0001 (6)0.0033 (7)
C330.0613 (11)0.0925 (15)0.0619 (11)0.0137 (10)0.0109 (9)0.0024 (10)
Geometric parameters (Å, º) top
O11—C111.2414 (15)C22—C231.506 (3)
O12—N11.3887 (15)C22—H22A0.97
O12—H120.82C22—H22B0.97
N1—C111.3103 (18)C23—H23A0.96
N1—H10.86C23—H23B0.96
C11—C121.5048 (18)C23—H23C0.96
C12—C131.507 (2)O31—C311.2472 (16)
C12—H12A0.97O32—N31.3854 (15)
C12—H12B0.97O32—H320.82
C13—H13A0.96N3—C311.3117 (19)
C13—H13B0.96N3—H30.86
C13—H13C0.96C31—C321.501 (2)
O21—C211.2435 (15)C32—C331.489 (3)
O22—N21.3872 (14)C32—H32A0.97
O22—H220.82C32—H32B0.97
N2—C211.3121 (17)C33—H33A0.96
N2—H20.86C33—H33B0.96
C21—C221.5055 (18)C33—H33C0.96
N1—O12—H12109.5C21—C22—H22B109.1
C11—N1—O12119.16 (10)C23—C22—H22B109.1
C11—N1—H1120.4H22A—C22—H22B107.9
O12—N1—H1120.4C22—C23—H23A109.5
O11—C11—N1122.96 (12)C22—C23—H23B109.5
O11—C11—C12121.78 (13)H23A—C23—H23B109.5
N1—C11—C12115.26 (11)C22—C23—H23C109.5
C11—C12—C13113.63 (12)H23A—C23—H23C109.5
C11—C12—H12A108.8H23B—C23—H23C109.5
C13—C12—H12A108.8N3—O32—H32109.5
C11—C12—H12B108.8C31—N3—O32120.71 (11)
C13—C12—H12B108.8C31—N3—H3119.6
H12A—C12—H12B107.7O32—N3—H3119.6
C12—C13—H13A109.5O31—C31—N3123.14 (13)
C12—C13—H13B109.5O31—C31—C32122.00 (14)
H13A—C13—H13B109.5N3—C31—C32114.84 (12)
C12—C13—H13C109.5C33—C32—C31112.07 (13)
H13A—C13—H13C109.5C33—C32—H32A109.2
H13B—C13—H13C109.5C31—C32—H32A109.2
N2—O22—H22109.5C33—C32—H32B109.2
C21—N2—O22119.70 (10)C31—C32—H32B109.2
C21—N2—H2120.1H32A—C32—H32B107.9
O22—N2—H2120.1C32—C33—H33A109.5
O21—C21—N2122.48 (12)C32—C33—H33B109.5
O21—C21—C22122.15 (12)H33A—C33—H33B109.5
N2—C21—C22115.37 (11)C32—C33—H33C109.5
C21—C22—C23112.37 (14)H33A—C33—H33C109.5
C21—C22—H22A109.1H33B—C33—H33C109.5
C23—C22—H22A109.1
O12—N1—C11—O118.5 (2)O21—C21—C22—C2360.6 (2)
O12—N1—C11—C12170.73 (11)N2—C21—C22—C23118.96 (16)
O11—C11—C12—C1346.0 (2)O32—N3—C31—O311.6 (2)
N1—C11—C12—C13134.74 (14)O32—N3—C31—C32179.98 (12)
O22—N2—C21—O216.6 (2)O31—C31—C32—C3366.7 (2)
O22—N2—C21—C22172.96 (12)N3—C31—C32—C33111.78 (17)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O12—H12···O21i0.821.842.6589 (15)175
N1—H1···O21ii0.862.052.8958 (15)166
O22—H22···O110.821.842.6624 (16)177
N2—H2···O31iii0.862.032.8609 (16)163
O32—H32···O31iii0.821.882.6775 (17)165
N3—H3···O110.861.952.8012 (16)168
Symmetry codes: (i) x, y+1/2, z+1/2; (ii) x, y1/2, z+1/2; (iii) x+1, y+1/2, z+1/2.
Selected geometric parameters (Å, °) top
Parametern = 1n = 2n = 3
On1-Cn11.2414 (15)1.2435 (15)1.2472 (16)
Cn1-Nn1.3103 (18)1.3121 (17)1.3117 (19)
Nn-On21.3887 (15)1.3872 (14)1.3854 (15)
On1-Cn1-Nn-On2-8.5 (2)-6.6 (2)-1.6 (2)
Nn-Cn1-Cn2-Cn3134.74 (14)-118.96 (16)111.78 (17)
Angles (°) around the carbonyl O acceptor sites top
Parametern = 1n = 2n = 3
Cn1-On1···O124.01 (9)116.47 (9)118.34 (10)
Cn1-On1···N140.71 (10)133.14 (9)138.13 (10)
O···On1···N95.06 (5)110.36 (5)99.39 (5)
O and N donors are defined in Table 1
 

Follow Acta Cryst. C
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds