organic compounds
The title compound, N-hydroxypropanamide, C3H7NO2, crystallizes with Z' = 3 in P21/c. The molecules are linked by three N-HO hydrogen bonds [NO 2.8012 (16) to 2.8958 (15) Å; N-HO 163 to 168°] and by three O-HO hydrogen bonds [OO 2.6589 (15) to 2.6775 (17) Å; O-HO 165 to 177°] into a single three-dimensional framework.
Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270101000075/sk1449sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270101000075/sk1449Isup2.hkl |
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
C3H7NO2 | F(000) = 576 |
Mr = 89.10 | Dx = 1.282 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 12.052 (3) Å | Cell parameters from 25 reflections |
b = 8.009 (3) Å | θ = 9.8–11.2° |
c = 14.354 (3) Å | µ = 0.11 mm−1 |
β = 92.35 (2)° | T = 293 K |
V = 1384.3 (7) Å3 | Block, colourless |
Z = 12 | 0.40 × 0.40 × 0.40 mm |
Data collection top
Nonius CAD4 diffractometer | Rint = 0.017 |
Radiation source: fine-focus sealed X-ray tube | θmax = 27.0°, θmin = 2.8° |
Graphite monochromator | h = 0→15 |
θ/2θ scans | k = 0→10 |
3374 measured reflections | l = −18→18 |
3016 independent reflections | 3 standard reflections every 120 min |
2426 reflections with I > 2σ(I) | intensity decay: none |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.038 | H-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 reflections | Δρmax = 0.19 e Å−3 |
170 parameters | Δρmin = −0.28 e Å−3 |
0 restraints | Extinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.026 (3) |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
x | y | z | Uiso*/Ueq | ||
O11 | 0.16302 (8) | 0.37086 (14) | 0.32034 (9) | 0.0536 (3) | |
O12 | 0.12245 (8) | 0.05820 (13) | 0.37449 (7) | 0.0456 (3) | |
N1 | 0.04621 (8) | 0.18708 (15) | 0.38178 (8) | 0.0372 (3) | |
C11 | 0.07007 (10) | 0.33463 (17) | 0.34863 (9) | 0.0348 (3) | |
C12 | −0.02402 (11) | 0.45828 (19) | 0.34589 (11) | 0.0433 (3) | |
C13 | 0.00887 (14) | 0.6290 (2) | 0.38140 (13) | 0.0562 (4) | |
O21 | 0.15986 (7) | 0.57334 (15) | 0.04293 (7) | 0.0483 (3) | |
O22 | 0.20525 (8) | 0.64442 (13) | 0.22256 (7) | 0.0427 (3) | |
N2 | 0.28637 (8) | 0.60463 (15) | 0.16042 (8) | 0.0376 (3) | |
C21 | 0.25830 (10) | 0.57854 (17) | 0.07233 (9) | 0.0351 (3) | |
C22 | 0.35365 (11) | 0.5567 (2) | 0.00888 (10) | 0.0462 (4) | |
C23 | 0.35481 (16) | 0.6881 (3) | −0.06606 (13) | 0.0671 (5) | |
O31 | 0.50451 (8) | 0.08237 (15) | 0.23862 (8) | 0.0496 (3) | |
O32 | 0.45586 (9) | 0.31530 (15) | 0.36718 (8) | 0.0503 (3) | |
N3 | 0.37691 (9) | 0.23735 (16) | 0.30936 (9) | 0.0423 (3) | |
C31 | 0.40608 (10) | 0.12399 (17) | 0.24912 (10) | 0.0375 (3) | |
C32 | 0.31184 (12) | 0.0503 (2) | 0.19124 (12) | 0.0491 (4) | |
C33 | 0.31564 (16) | 0.0997 (3) | 0.09140 (14) | 0.0723 (6) | |
H12 | 0.1322 | 0.0128 | 0.4254 | 0.068* | |
H1 | −0.0159 | 0.1703 | 0.4077 | 0.045* | |
H12A | −0.0831 | 0.4155 | 0.3831 | 0.052* | |
H12B | −0.0531 | 0.4685 | 0.2821 | 0.052* | |
H13A | 0.0432 | 0.6192 | 0.4427 | 0.084* | |
H13B | −0.0560 | 0.6982 | 0.3839 | 0.084* | |
H13C | 0.0604 | 0.6784 | 0.3402 | 0.084* | |
H22 | 0.1902 | 0.5614 | 0.2530 | 0.064* | |
H2 | 0.3547 | 0.5971 | 0.1795 | 0.045* | |
H22A | 0.3486 | 0.4473 | −0.0200 | 0.055* | |
H22B | 0.4229 | 0.5615 | 0.0456 | 0.055* | |
H23A | 0.2864 | 0.6838 | −0.1027 | 0.101* | |
H23B | 0.4159 | 0.6681 | −0.1054 | 0.101* | |
H23C | 0.3628 | 0.7963 | −0.0378 | 0.101* | |
H32 | 0.4750 | 0.4031 | 0.3432 | 0.075* | |
H3 | 0.3080 | 0.2636 | 0.3130 | 0.051* | |
H32A | 0.3149 | −0.0705 | 0.1959 | 0.059* | |
H32B | 0.2420 | 0.0869 | 0.2157 | 0.059* | |
H33A | 0.3036 | 0.2179 | 0.0857 | 0.108* | |
H33B | 0.2588 | 0.0413 | 0.0558 | 0.108* | |
H33C | 0.3870 | 0.0720 | 0.0683 | 0.108* |
Atomic displacement parameters (Å2) top
U11 | U22 | U33 | U12 | U13 | U23 | |
O11 | 0.0317 (5) | 0.0521 (6) | 0.0784 (8) | 0.0049 (4) | 0.0193 (5) | 0.0184 (6) |
O12 | 0.0445 (5) | 0.0481 (6) | 0.0446 (5) | 0.0145 (4) | 0.0054 (4) | 0.0095 (4) |
N1 | 0.0256 (5) | 0.0436 (6) | 0.0427 (6) | 0.0034 (4) | 0.0056 (4) | 0.0060 (5) |
C11 | 0.0255 (6) | 0.0445 (7) | 0.0345 (6) | 0.0023 (5) | 0.0024 (5) | 0.0034 (5) |
C12 | 0.0312 (6) | 0.0484 (8) | 0.0502 (8) | 0.0074 (6) | 0.0018 (6) | 0.0044 (6) |
C13 | 0.0560 (9) | 0.0511 (9) | 0.0624 (10) | 0.0063 (7) | 0.0140 (8) | −0.0039 (8) |
O21 | 0.0266 (5) | 0.0720 (7) | 0.0463 (6) | 0.0015 (4) | −0.0008 (4) | −0.0150 (5) |
O22 | 0.0426 (5) | 0.0453 (6) | 0.0413 (5) | 0.0016 (4) | 0.0134 (4) | 0.0008 (4) |
N2 | 0.0255 (5) | 0.0491 (7) | 0.0383 (6) | 0.0012 (5) | 0.0028 (4) | −0.0006 (5) |
C21 | 0.0262 (6) | 0.0381 (7) | 0.0411 (7) | 0.0012 (5) | 0.0030 (5) | −0.0038 (5) |
C22 | 0.0309 (6) | 0.0637 (10) | 0.0446 (8) | 0.0037 (6) | 0.0078 (6) | −0.0067 (7) |
C23 | 0.0664 (11) | 0.0741 (12) | 0.0622 (11) | −0.0079 (9) | 0.0219 (9) | 0.0051 (9) |
O31 | 0.0274 (5) | 0.0599 (7) | 0.0614 (7) | 0.0068 (4) | 0.0002 (4) | −0.0054 (5) |
O32 | 0.0449 (6) | 0.0546 (7) | 0.0509 (6) | −0.0078 (5) | −0.0063 (5) | −0.0010 (5) |
N3 | 0.0250 (5) | 0.0468 (7) | 0.0553 (7) | −0.0010 (5) | 0.0015 (5) | −0.0017 (6) |
C31 | 0.0259 (6) | 0.0384 (7) | 0.0482 (7) | −0.0013 (5) | 0.0022 (5) | 0.0084 (6) |
C32 | 0.0329 (7) | 0.0487 (8) | 0.0654 (10) | −0.0083 (6) | −0.0001 (6) | −0.0033 (7) |
C33 | 0.0613 (11) | 0.0925 (15) | 0.0619 (11) | −0.0137 (10) | −0.0109 (9) | 0.0024 (10) |
Geometric parameters (Å, º) top
O11—C11 | 1.2414 (15) | C22—C23 | 1.506 (3) |
O12—N1 | 1.3887 (15) | C22—H22A | 0.97 |
O12—H12 | 0.82 | C22—H22B | 0.97 |
N1—C11 | 1.3103 (18) | C23—H23A | 0.96 |
N1—H1 | 0.86 | C23—H23B | 0.96 |
C11—C12 | 1.5048 (18) | C23—H23C | 0.96 |
C12—C13 | 1.507 (2) | O31—C31 | 1.2472 (16) |
C12—H12A | 0.97 | O32—N3 | 1.3854 (15) |
C12—H12B | 0.97 | O32—H32 | 0.82 |
C13—H13A | 0.96 | N3—C31 | 1.3117 (19) |
C13—H13B | 0.96 | N3—H3 | 0.86 |
C13—H13C | 0.96 | C31—C32 | 1.501 (2) |
O21—C21 | 1.2435 (15) | C32—C33 | 1.489 (3) |
O22—N2 | 1.3872 (14) | C32—H32A | 0.97 |
O22—H22 | 0.82 | C32—H32B | 0.97 |
N2—C21 | 1.3121 (17) | C33—H33A | 0.96 |
N2—H2 | 0.86 | C33—H33B | 0.96 |
C21—C22 | 1.5055 (18) | C33—H33C | 0.96 |
N1—O12—H12 | 109.5 | C21—C22—H22B | 109.1 |
C11—N1—O12 | 119.16 (10) | C23—C22—H22B | 109.1 |
C11—N1—H1 | 120.4 | H22A—C22—H22B | 107.9 |
O12—N1—H1 | 120.4 | C22—C23—H23A | 109.5 |
O11—C11—N1 | 122.96 (12) | C22—C23—H23B | 109.5 |
O11—C11—C12 | 121.78 (13) | H23A—C23—H23B | 109.5 |
N1—C11—C12 | 115.26 (11) | C22—C23—H23C | 109.5 |
C11—C12—C13 | 113.63 (12) | H23A—C23—H23C | 109.5 |
C11—C12—H12A | 108.8 | H23B—C23—H23C | 109.5 |
C13—C12—H12A | 108.8 | N3—O32—H32 | 109.5 |
C11—C12—H12B | 108.8 | C31—N3—O32 | 120.71 (11) |
C13—C12—H12B | 108.8 | C31—N3—H3 | 119.6 |
H12A—C12—H12B | 107.7 | O32—N3—H3 | 119.6 |
C12—C13—H13A | 109.5 | O31—C31—N3 | 123.14 (13) |
C12—C13—H13B | 109.5 | O31—C31—C32 | 122.00 (14) |
H13A—C13—H13B | 109.5 | N3—C31—C32 | 114.84 (12) |
C12—C13—H13C | 109.5 | C33—C32—C31 | 112.07 (13) |
H13A—C13—H13C | 109.5 | C33—C32—H32A | 109.2 |
H13B—C13—H13C | 109.5 | C31—C32—H32A | 109.2 |
N2—O22—H22 | 109.5 | C33—C32—H32B | 109.2 |
C21—N2—O22 | 119.70 (10) | C31—C32—H32B | 109.2 |
C21—N2—H2 | 120.1 | H32A—C32—H32B | 107.9 |
O22—N2—H2 | 120.1 | C32—C33—H33A | 109.5 |
O21—C21—N2 | 122.48 (12) | C32—C33—H33B | 109.5 |
O21—C21—C22 | 122.15 (12) | H33A—C33—H33B | 109.5 |
N2—C21—C22 | 115.37 (11) | C32—C33—H33C | 109.5 |
C21—C22—C23 | 112.37 (14) | H33A—C33—H33C | 109.5 |
C21—C22—H22A | 109.1 | H33B—C33—H33C | 109.5 |
C23—C22—H22A | 109.1 | ||
O12—N1—C11—O11 | −8.5 (2) | O21—C21—C22—C23 | 60.6 (2) |
O12—N1—C11—C12 | 170.73 (11) | N2—C21—C22—C23 | −118.96 (16) |
O11—C11—C12—C13 | −46.0 (2) | O32—N3—C31—O31 | −1.6 (2) |
N1—C11—C12—C13 | 134.74 (14) | O32—N3—C31—C32 | 179.98 (12) |
O22—N2—C21—O21 | −6.6 (2) | O31—C31—C32—C33 | −66.7 (2) |
O22—N2—C21—C22 | 172.96 (12) | N3—C31—C32—C33 | 111.78 (17) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O12—H12···O21i | 0.82 | 1.84 | 2.6589 (15) | 175 |
N1—H1···O21ii | 0.86 | 2.05 | 2.8958 (15) | 166 |
O22—H22···O11 | 0.82 | 1.84 | 2.6624 (16) | 177 |
N2—H2···O31iii | 0.86 | 2.03 | 2.8609 (16) | 163 |
O32—H32···O31iii | 0.82 | 1.88 | 2.6775 (17) | 165 |
N3—H3···O11 | 0.86 | 1.95 | 2.8012 (16) | 168 |
Symmetry codes: (i) x, −y+1/2, z+1/2; (ii) −x, y−1/2, −z+1/2; (iii) −x+1, y+1/2, −z+1/2. |
Selected geometric parameters (Å, °) top
Parameter | n = 1 | n = 2 | n = 3 |
On1-Cn1 | 1.2414 (15) | 1.2435 (15) | 1.2472 (16) |
Cn1-Nn | 1.3103 (18) | 1.3121 (17) | 1.3117 (19) |
Nn-On2 | 1.3887 (15) | 1.3872 (14) | 1.3854 (15) |
On1-Cn1-Nn-On2 | -8.5 (2) | -6.6 (2) | -1.6 (2) |
Nn-Cn1-Cn2-Cn3 | 134.74 (14) | -118.96 (16) | 111.78 (17) |
Angles (°) around the carbonyl O acceptor sites top
Parameter | n = 1 | n = 2 | n = 3 |
Cn1-On1···O | 124.01 (9) | 116.47 (9) | 118.34 (10) |
Cn1-On1···N | 140.71 (10) | 133.14 (9) | 138.13 (10) |
O···On1···N | 95.06 (5) | 110.36 (5) | 99.39 (5) |
O and N donors are defined in Table 1 |