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4,5-Dimethyl-1,3-dioxol-2-one crystallizes on a mirror plane in P21/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

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2056989022009239/gg4011sup1.cif
Contains datablocks I, global

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2056989022009239/gg4011Isup2.cml
Supplementary material

CCDC reference: 2207848

Key indicators

  • Single-crystal X-ray study
  • T = 100 K
  • Mean [sigma](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

Computing details top

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
C5H6O3F(000) = 120
Mr = 114.10Dx = 1.479 Mg m3
Monoclinic, P21/mMo Kα radiation, λ = 0.71073 Å
a = 3.8283 (10) ÅCell parameters from 2113 reflections
b = 10.972 (2) Åθ = 3.2–28.3°
c = 6.1096 (10) ŵ = 0.12 mm1
β = 93.523 (2)°T = 100 K
V = 256.15 (10) Å3Block, white
Z = 20.27 × 0.21 × 0.16 mm
Data collection top
Bruker SMART APEX
diffractometer
636 independent reflections
Radiation source: fine-focus sealed tube617 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.027
π and ο scansθmax = 28.3°, θmin = 3.3°
Absorption correction: multi-scan
(SADABS; Krause et al., 2015)
h = 44
Tmin = 0.967, Tmax = 0.980k = 1414
2310 measured reflectionsl = 88
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)] = 0.030H-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 reflectionsΔρmax = 0.30 e Å3
42 parametersΔρmin = 0.21 e Å3
0 restraintsExtinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction 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
xyzUiso*/Ueq
O10.1654 (3)0.2500000.67266 (16)0.0247 (3)
O20.08340 (16)0.35049 (6)0.94742 (10)0.0174 (2)
C10.0147 (3)0.2500000.8382 (2)0.0177 (3)
C20.2444 (2)0.31041 (8)1.13620 (13)0.0156 (2)
C30.3662 (2)0.40519 (8)1.28542 (15)0.0190 (2)
H3A0.4795000.3664091.4070010.028*
H3B0.5341680.4586111.2048400.028*
H3C0.1658820.4534081.3434020.028*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0293 (6)0.0271 (5)0.0186 (5)0.0000.0091 (4)0.000
O20.0204 (4)0.0160 (4)0.0162 (4)0.0002 (2)0.0045 (2)0.0011 (2)
C10.0185 (6)0.0176 (6)0.0169 (6)0.0000.0008 (4)0.000
C20.0145 (4)0.0180 (5)0.0145 (4)0.0006 (3)0.0020 (3)0.0009 (3)
C30.0206 (5)0.0168 (4)0.0199 (4)0.0004 (3)0.0044 (3)0.0027 (3)
Geometric parameters (Å, º) top
O1—C11.1949 (16)C2—C31.4773 (12)
O2—C11.3537 (10)C3—H3A0.9800
O2—C21.4110 (10)C3—H3B0.9800
C2—C2i1.3257 (18)C3—H3C0.9800
C1—O2—C2107.30 (7)C2—C3—H3A109.5
O1—C1—O2i125.46 (5)C2—C3—H3B109.5
O1—C1—O2125.46 (5)H3A—C3—H3B109.5
O2i—C1—O2109.07 (10)C2—C3—H3C109.5
C2i—C2—O2108.16 (4)H3A—C3—H3C109.5
C2i—C2—C3134.74 (5)H3B—C3—H3C109.5
O2—C2—C3117.09 (7)
C2—O2—C1—O1178.43 (12)C1—O2—C2—C2i0.72 (8)
C2—O2—C1—O2i1.19 (12)C1—O2—C2—C3178.50 (8)
Symmetry code: (i) x, y+1/2, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C3—H3A···O1ii0.982.533.4976 (13)171
Symmetry code: (ii) x1, y, z+1.
 

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