4,5-Dimethyl-1,3-dioxol-2-one crystallizes on a mirror plane in
P2
1/
m and forms layered sheets that comprise antiparallel linear strands. Close O

H, C

O and C

C intermolecular contacts are formed between strands and sheets.
Supporting information
CCDC reference: 2207848
Key indicators
- Single-crystal X-ray study
- T = 100 K
- Mean
(C-C) = 0.001 Å
- R factor = 0.030
- wR factor = 0.077
- Data-to-parameter ratio = 15.1
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 1 Note
C5 H6 O3
Alert level G
PLAT012_ALERT_1_G N.O.K. _shelx_res_checksum Found in CIF ...... Please Check
PLAT066_ALERT_1_G Predicted and Reported Tmin&Tmax Range Identical ? Check
PLAT398_ALERT_2_G Deviating C-O-C Angle From 120 for O2 . 107.3 Degree
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
3 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
1 ALERT type 4 Improvement, methodology, query or suggestion
0 ALERT type 5 Informative message, check
Data collection: SMART (Bruker, 2000); cell refinement: SMART (Bruker, 2000); data reduction: SAINT-Plus (Bruker, 2004); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL (Sheldrick, 2015b); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).
4,5-Dimethyl-1,3-dioxol-2-one
top
Crystal data top
C5H6O3 | F(000) = 120 |
Mr = 114.10 | Dx = 1.479 Mg m−3 |
Monoclinic, P21/m | Mo Kα radiation, λ = 0.71073 Å |
a = 3.8283 (10) Å | Cell parameters from 2113 reflections |
b = 10.972 (2) Å | θ = 3.2–28.3° |
c = 6.1096 (10) Å | µ = 0.12 mm−1 |
β = 93.523 (2)° | T = 100 K |
V = 256.15 (10) Å3 | Block, white |
Z = 2 | 0.27 × 0.21 × 0.16 mm |
Data collection top
Bruker SMART APEX diffractometer | 636 independent reflections |
Radiation source: fine-focus sealed tube | 617 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.027 |
π and ο scans | θmax = 28.3°, θmin = 3.3° |
Absorption correction: multi-scan (SADABS; Krause et al., 2015) | h = −4→4 |
Tmin = 0.967, Tmax = 0.980 | k = −14→14 |
2310 measured reflections | l = −8→8 |
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)] = 0.030 | H-atom parameters constrained |
wR(F2) = 0.077 | w = 1/[σ2(Fo2) + (0.0345P)2 + 0.0767P] where P = (Fo2 + 2Fc2)/3 |
S = 1.10 | (Δ/σ)max < 0.001 |
636 reflections | Δρmax = 0.30 e Å−3 |
42 parameters | Δρmin = −0.21 e Å−3 |
0 restraints | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.22 (2) |
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. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F2, conventional R-factors R are based
on F, with F set to zero for negative F2. The threshold expression of
F2 > 2sigma(F2) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F2 are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger. Hydrogen atoms were added in calculated positions and refined with isotropic
displacement parameters that are approximately 1.5 times those of the carbon
atom to which they are attached. The C–H distances assumed were 0.98 Å. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
O1 | 0.1654 (3) | 0.250000 | 0.67266 (16) | 0.0247 (3) | |
O2 | −0.08340 (16) | 0.35049 (6) | 0.94742 (10) | 0.0174 (2) | |
C1 | 0.0147 (3) | 0.250000 | 0.8382 (2) | 0.0177 (3) | |
C2 | −0.2444 (2) | 0.31041 (8) | 1.13620 (13) | 0.0156 (2) | |
C3 | −0.3662 (2) | 0.40519 (8) | 1.28542 (15) | 0.0190 (2) | |
H3A | −0.479500 | 0.366409 | 1.407001 | 0.028* | |
H3B | −0.534168 | 0.458611 | 1.204840 | 0.028* | |
H3C | −0.165882 | 0.453408 | 1.343402 | 0.028* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0293 (6) | 0.0271 (5) | 0.0186 (5) | 0.000 | 0.0091 (4) | 0.000 |
O2 | 0.0204 (4) | 0.0160 (4) | 0.0162 (4) | −0.0002 (2) | 0.0045 (2) | 0.0011 (2) |
C1 | 0.0185 (6) | 0.0176 (6) | 0.0169 (6) | 0.000 | 0.0008 (4) | 0.000 |
C2 | 0.0145 (4) | 0.0180 (5) | 0.0145 (4) | −0.0006 (3) | 0.0020 (3) | 0.0009 (3) |
C3 | 0.0206 (5) | 0.0168 (4) | 0.0199 (4) | 0.0004 (3) | 0.0044 (3) | −0.0027 (3) |
Geometric parameters (Å, º) top
O1—C1 | 1.1949 (16) | C2—C3 | 1.4773 (12) |
O2—C1 | 1.3537 (10) | C3—H3A | 0.9800 |
O2—C2 | 1.4110 (10) | C3—H3B | 0.9800 |
C2—C2i | 1.3257 (18) | C3—H3C | 0.9800 |
| | | |
C1—O2—C2 | 107.30 (7) | C2—C3—H3A | 109.5 |
O1—C1—O2i | 125.46 (5) | C2—C3—H3B | 109.5 |
O1—C1—O2 | 125.46 (5) | H3A—C3—H3B | 109.5 |
O2i—C1—O2 | 109.07 (10) | C2—C3—H3C | 109.5 |
C2i—C2—O2 | 108.16 (4) | H3A—C3—H3C | 109.5 |
C2i—C2—C3 | 134.74 (5) | H3B—C3—H3C | 109.5 |
O2—C2—C3 | 117.09 (7) | | |
| | | |
C2—O2—C1—O1 | −178.43 (12) | C1—O2—C2—C2i | −0.72 (8) |
C2—O2—C1—O2i | 1.19 (12) | C1—O2—C2—C3 | 178.50 (8) |
Symmetry code: (i) x, −y+1/2, z. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C3—H3A···O1ii | 0.98 | 2.53 | 3.4976 (13) | 171 |
Symmetry code: (ii) x−1, y, z+1. |