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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

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108768108010197/bs5059sup1.cif
Contains datablock ETOX

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768108010197/bs5059sup2.hkl
Structure factor file (original version)

pdf

Portable Document Format (PDF) file https://doi.org/10.1107/S0108768108010197/bs5059sup3.pdf
Supplementary material

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768108010197/bs5059sup4.hkl
Structure factor file (new version supplied by the authors on 19 June 2008)

CCDC reference: 691554

Computing details top

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).

Figures top
[Figure 1]
[Figure 2]
(ETOX) top
Crystal data top
C2H4OF(000) = 96
Mr = 44.05Dx = 1.162 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71068 Å
Hall symbol: -P 2ynCell parameters from 4382 reflections
a = 4.633 (5) Åθ = 4.0–45.0°
b = 8.400 (1) ŵ = 0.09 mm1
c = 6.577 (3) ÅT = 100 K
β = 100.37 (6)°Block, colourless
V = 251.8 (3) Å30.30 × 0.30 × 0.30 mm
Z = 4
Data collection top
Point detector
diffractometer
Rint = 0.029
Radiation source: fine-focus sealed tubeθmax = 45.0°, θmin = 4.0°
Graphite monochromatorh = 39
phi scansk = 1616
4382 measured reflectionsl = 1213
2081 independent reflections3 standard reflections every 60 min
1424 reflections with > 3σ(I) intensity decay: none
Refinement top
Refinement on FPrimary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.030Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.046H-atom parameters not refined
S = 1.33 w1 = 1/[s2(Fo)]
1424 reflections(Δ/σ)max < 0.001
79 parametersΔρmax = 0.16 e Å3
0 restraintsΔρmin = 0.14 e Å3
Crystal data top
C2H4OV = 251.8 (3) Å3
Mr = 44.05Z = 4
Monoclinic, P21/nMo Kα radiation
a = 4.633 (5) ŵ = 0.09 mm1
b = 8.400 (1) ÅT = 100 K
c = 6.577 (3) Å0.30 × 0.30 × 0.30 mm
β = 100.37 (6)°
Data collection top
Point detector
diffractometer
Rint = 0.029
4382 measured reflections3 standard reflections every 60 min
2081 independent reflections intensity decay: none
1424 reflections with > 3σ(I)
Refinement top
R[F2 > 2σ(F2)] = 0.0300 restraints
wR(F2) = 0.046H-atom parameters not refined
S = 1.33Δρmax = 0.16 e Å3
1424 reflectionsΔρmin = 0.14 e Å3
79 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.11724 (14)0.83112 (6)0.12422 (9)0.029
C10.14839 (10)0.93872 (5)0.29595 (6)0.028
C20.13430 (11)0.86471 (5)0.21815 (7)0.032
H10.2849670.8921480.4374650.0453
H20.1787971.0647350.2601990.051247
H30.3111620.9321170.1216990.044875
H40.2026930.7636160.304380.052954
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0342 (2)0.02514 (17)0.0292 (2)0.0030 (2)0.00965 (19)0.00383 (17)
C10.0318 (2)0.02463 (14)0.02690 (16)0.00004 (14)0.00516 (14)0.00206 (14)
C20.0300 (2)0.03357 (17)0.03388 (19)0.00343 (15)0.01159 (16)0.00051 (16)
H10.0453000.0461780.0354110.0025460.0042300.005772
H20.0512470.0307590.0478230.0010950.0137860.000034
H30.0448750.0491650.0461490.0018020.0086380.004251
H40.0529540.0429440.0480240.0032320.0195660.007580
Geometric parameters (Å, º) top
O1—C11.4335 (17)C1—H21.0989
O1—C21.4417 (18)C2—H31.0988
C1—C21.4568 (17)C2—H41.0990
C1—H11.0990
C1—O1—C260.89 (4)O1—C2—C159.28 (7)
O1—C1—C259.84 (7)O1—C2—H3115.45
O1—C1—H1113.82O1—C2—H4113.60
O1—C1—H2115.94C1—C2—H3120.84
C2—C1—H1119.32C1—C2—H4118.23
C2—C1—H2118.54H3—C2—H4116.22
H1—C1—H2116.59
C2—O1—C1—H1111.26H1—C1—C2—O1102.08
C2—O1—C1—H2109.38H1—C1—C2—H3154.78
C1—O1—C2—H3112.19H1—C1—C2—H40.01
C1—O1—C2—H4109.92H2—C1—C2—O1105.06
O1—C1—C2—H3103.14H2—C1—C2—H31.92
O1—C1—C2—H4102.09H2—C1—C2—H4152.85

Experimental details

Crystal data
Chemical formulaC2H4O
Mr44.05
Crystal system, space groupMonoclinic, P21/n
Temperature (K)100
a, b, c (Å)4.633 (5), 8.400 (1), 6.577 (3)
β (°) 100.37 (6)
V3)251.8 (3)
Z4
Radiation typeMo Kα
µ (mm1)0.09
Crystal size (mm)0.30 × 0.30 × 0.30
Data collection
DiffractometerPoint detector
diffractometer
Absorption correction
No. of measured, independent and
observed [ > 3σ(I)] reflections
4382, 2081, 1424
Rint0.029
(sin θ/λ)max1)0.995
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.030, 0.046, 1.33
No. of reflections1424
No. of parameters79
H-atom treatmentH-atom parameters not refined
Δρmax, Δρmin (e Å3)0.16, 0.14

Computer programs: SHELXS97 (Sheldrick, 2008), XD (Volkov et al., 2006).

Selected geometric parameters (Å, º) top
O1—C11.4335 (17)C1—H21.0989
O1—C21.4417 (18)C2—H31.0988
C1—C21.4568 (17)C2—H41.0990
C1—H11.0990
C1—O1—C260.89 (4)O1—C2—C159.28 (7)
O1—C1—C259.84 (7)O1—C2—H3115.45
O1—C1—H1113.82O1—C2—H4113.60
O1—C1—H2115.94C1—C2—H3120.84
C2—C1—H1119.32C1—C2—H4118.23
C2—C1—H2118.54H3—C2—H4116.22
H1—C1—H2116.59
C2—O1—C1—H1111.26H1—C1—C2—O1102.08
C2—O1—C1—H2109.38H1—C1—C2—H3154.78
C1—O1—C2—H3112.19H1—C1—C2—H40.01
C1—O1—C2—H4109.92H2—C1—C2—O1105.06
O1—C1—C2—H3103.14H2—C1—C2—H31.92
O1—C1—C2—H4102.09H2—C1—C2—H4152.85
 

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