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The experimental electron density of ethylene oxide was derived from a multipole refinement of 100 K X-ray data and complemented by density-functional calculations at experimental and optimized geometry. Atomic and bond-topological properties were derived using the atoms-in-molecules (AIM) formalism. The high strain in the three-membered ring molecule is mainly expressed by the high ellipticities of the three bonds in this ring, while the bond paths are only slightly bent for the C—C bond, but are virtually straight for the C—O bond.
Supporting information
CCDC reference: 691554
Program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: XD (Volkov et al., 2006); molecular graphics: XD (Volkov et al., 2006); software used to prepare material for publication: XD (Volkov et al., 2006).
Crystal data top
C2H4O | F(000) = 96 |
Mr = 44.05 | Dx = 1.162 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71068 Å |
Hall symbol: -P 2yn | Cell parameters from 4382 reflections |
a = 4.633 (5) Å | θ = 4.0–45.0° |
b = 8.400 (1) Å | µ = 0.09 mm−1 |
c = 6.577 (3) Å | T = 100 K |
β = 100.37 (6)° | Block, colourless |
V = 251.8 (3) Å3 | 0.30 × 0.30 × 0.30 mm |
Z = 4 | |
Data collection top
Point detector diffractometer | Rint = 0.029 |
Radiation source: fine-focus sealed tube | θmax = 45.0°, θmin = 4.0° |
Graphite monochromator | h = −3→9 |
phi scans | k = −16→16 |
4382 measured reflections | l = −12→13 |
2081 independent reflections | 3 standard reflections every 60 min |
1424 reflections with > 3σ(I) | intensity decay: none |
Refinement top
Refinement on F | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.030 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.046 | H-atom parameters not refined |
S = 1.33 | w1 = 1/[s2(Fo)] |
1424 reflections | (Δ/σ)max < 0.001 |
79 parameters | Δρmax = 0.16 e Å−3 |
0 restraints | Δρmin = −0.14 e Å−3 |
Crystal data top
C2H4O | V = 251.8 (3) Å3 |
Mr = 44.05 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 4.633 (5) Å | µ = 0.09 mm−1 |
b = 8.400 (1) Å | T = 100 K |
c = 6.577 (3) Å | 0.30 × 0.30 × 0.30 mm |
β = 100.37 (6)° | |
Data collection top
Point detector diffractometer | Rint = 0.029 |
4382 measured reflections | 3 standard reflections every 60 min |
2081 independent reflections | intensity decay: none |
1424 reflections with > 3σ(I) | |
Refinement top
R[F2 > 2σ(F2)] = 0.030 | 0 restraints |
wR(F2) = 0.046 | H-atom parameters not refined |
S = 1.33 | Δρmax = 0.16 e Å−3 |
1424 reflections | Δρmin = −0.14 e Å−3 |
79 parameters | |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
O1 | 0.11724 (14) | 0.83112 (6) | 0.12422 (9) | 0.029 | |
C1 | 0.14839 (10) | 0.93872 (5) | 0.29595 (6) | 0.028 | |
C2 | −0.13430 (11) | 0.86471 (5) | 0.21815 (7) | 0.032 | |
H1 | 0.284967 | 0.892148 | 0.437465 | 0.0453 | |
H2 | 0.178797 | 1.064735 | 0.260199 | 0.051247 | |
H3 | −0.311162 | 0.932117 | 0.121699 | 0.044875 | |
H4 | −0.202693 | 0.763616 | 0.30438 | 0.052954 | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0342 (2) | 0.02514 (17) | 0.0292 (2) | 0.0030 (2) | 0.00965 (19) | −0.00383 (17) |
C1 | 0.0318 (2) | 0.02463 (14) | 0.02690 (16) | −0.00004 (14) | 0.00516 (14) | −0.00206 (14) |
C2 | 0.0300 (2) | 0.03357 (17) | 0.03388 (19) | −0.00343 (15) | 0.01159 (16) | 0.00051 (16) |
H1 | 0.045300 | 0.046178 | 0.035411 | 0.002546 | 0.004230 | 0.005772 |
H2 | 0.051247 | 0.030759 | 0.047823 | 0.001095 | 0.013786 | −0.000034 |
H3 | 0.044875 | 0.049165 | 0.046149 | 0.001802 | 0.008638 | 0.004251 |
H4 | 0.052954 | 0.042944 | 0.048024 | 0.003232 | 0.019566 | −0.007580 |
Geometric parameters (Å, º) top
O1—C1 | 1.4335 (17) | C1—H2 | 1.0989 |
O1—C2 | 1.4417 (18) | C2—H3 | 1.0988 |
C1—C2 | 1.4568 (17) | C2—H4 | 1.0990 |
C1—H1 | 1.0990 | | |
| | | |
C1—O1—C2 | 60.89 (4) | O1—C2—C1 | 59.28 (7) |
O1—C1—C2 | 59.84 (7) | O1—C2—H3 | 115.45 |
O1—C1—H1 | 113.82 | O1—C2—H4 | 113.60 |
O1—C1—H2 | 115.94 | C1—C2—H3 | 120.84 |
C2—C1—H1 | 119.32 | C1—C2—H4 | 118.23 |
C2—C1—H2 | 118.54 | H3—C2—H4 | 116.22 |
H1—C1—H2 | 116.59 | | |
| | | |
C2—O1—C1—H1 | 111.26 | H1—C1—C2—O1 | −102.08 |
C2—O1—C1—H2 | −109.38 | H1—C1—C2—H3 | 154.78 |
C1—O1—C2—H3 | 112.19 | H1—C1—C2—H4 | 0.01 |
C1—O1—C2—H4 | −109.92 | H2—C1—C2—O1 | 105.06 |
O1—C1—C2—H3 | −103.14 | H2—C1—C2—H3 | 1.92 |
O1—C1—C2—H4 | 102.09 | H2—C1—C2—H4 | −152.85 |
Experimental details
Crystal data |
Chemical formula | C2H4O |
Mr | 44.05 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 100 |
a, b, c (Å) | 4.633 (5), 8.400 (1), 6.577 (3) |
β (°) | 100.37 (6) |
V (Å3) | 251.8 (3) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.09 |
Crystal size (mm) | 0.30 × 0.30 × 0.30 |
|
Data collection |
Diffractometer | Point detector diffractometer |
Absorption correction | – |
No. of measured, independent and observed [ > 3σ(I)] reflections | 4382, 2081, 1424 |
Rint | 0.029 |
(sin θ/λ)max (Å−1) | 0.995 |
|
Refinement |
R[F2 > 2σ(F2)], wR(F2), S | 0.030, 0.046, 1.33 |
No. of reflections | 1424 |
No. of parameters | 79 |
H-atom treatment | H-atom parameters not refined |
Δρmax, Δρmin (e Å−3) | 0.16, −0.14 |
Selected geometric parameters (Å, º) topO1—C1 | 1.4335 (17) | C1—H2 | 1.0989 |
O1—C2 | 1.4417 (18) | C2—H3 | 1.0988 |
C1—C2 | 1.4568 (17) | C2—H4 | 1.0990 |
C1—H1 | 1.0990 | | |
| | | |
C1—O1—C2 | 60.89 (4) | O1—C2—C1 | 59.28 (7) |
O1—C1—C2 | 59.84 (7) | O1—C2—H3 | 115.45 |
O1—C1—H1 | 113.82 | O1—C2—H4 | 113.60 |
O1—C1—H2 | 115.94 | C1—C2—H3 | 120.84 |
C2—C1—H1 | 119.32 | C1—C2—H4 | 118.23 |
C2—C1—H2 | 118.54 | H3—C2—H4 | 116.22 |
H1—C1—H2 | 116.59 | | |
| | | |
C2—O1—C1—H1 | 111.26 | H1—C1—C2—O1 | −102.08 |
C2—O1—C1—H2 | −109.38 | H1—C1—C2—H3 | 154.78 |
C1—O1—C2—H3 | 112.19 | H1—C1—C2—H4 | 0.01 |
C1—O1—C2—H4 | −109.92 | H2—C1—C2—O1 | 105.06 |
O1—C1—C2—H3 | −103.14 | H2—C1—C2—H3 | 1.92 |
O1—C1—C2—H4 | 102.09 | H2—C1—C2—H4 | −152.85 |
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