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Di­methyl fumarate, C6H8O4, crystallizes in the fully stretched planar conformation. The mol­ecule is located on a crystallographic inversion centre and has local symmetry 2/m. The fumarate mol­ecules aggregate in layers coinciding with the (1\overline 11) lattice planes.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804010177/lh6212sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804010177/lh6212Isup2.hkl
Contains datablock I

CCDC reference: 239304

Key indicators

  • Single-crystal X-ray study
  • T = 150 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.045
  • wR factor = 0.122
  • Data-to-parameter ratio = 10.3

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT480_ALERT_4_C Long H...A H-Bond Reported H1 .. O1 .. 2.65 Ang.
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 1 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 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

Computing details top

Data collection: COLLECT (Nonius, 1998); cell refinement: DENZO (Otwinowski & Minor, 1997); data reduction: DENZO; program(s) used to solve structure: SHELXS86 (Sheldrick, 1985); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: PLATON.

(I) top
Crystal data top
C6H8O4Z = 1
Mr = 144.12F(000) = 76
Triclinic, P1Quoted _cell_measurement_* data items refer to the initial cell determination. The cell parameters as reported in _cell_* are based on the complete data set.
Hall symbol: -P 1Dx = 1.429 Mg m3
a = 3.8680 (14) ÅMo Kα radiation, λ = 0.71073 Å
b = 5.643 (2) ÅCell parameters from 530 reflections
c = 8.364 (3) Åθ = 2.0–25.0°
α = 100.843 (16)°µ = 0.12 mm1
β = 100.289 (18)°T = 150 K
γ = 105.706 (14)°Irregular block, colourless
V = 167.44 (11) Å30.3 × 0.2 × 0.2 mm
Data collection top
Nonius KappaCCD area-detector
diffractometer
542 reflections with I > 2σ(I)
Radiation source: Rotating AnodeRint = 0.037
Graphite monochromatorθmax = 25.2°, θmin = 2.6°
Detector resolution: 18.4 pixels mm-1h = 43
φ scans and ω scans with κ offsetk = 66
1315 measured reflectionsl = 910
597 independent reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.045Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.122Only H-atom coordinates refined
S = 1.11 w = 1/[σ2(Fo2) + (0.0721P)2 + 0.03P]
where P = (Fo2 + 2Fc2)/3
597 reflections(Δ/σ)max < 0.001
58 parametersΔρmax = 0.24 e Å3
0 restraintsΔρmin = 0.26 e Å3
Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.2939 (3)0.53163 (19)0.19453 (13)0.0304 (4)
O20.0683 (3)0.2238 (2)0.28160 (14)0.0411 (4)
C10.0993 (4)0.1212 (3)0.02180 (18)0.0276 (5)
C20.0935 (4)0.2914 (3)0.17973 (18)0.0267 (5)
C30.3066 (5)0.7139 (3)0.3450 (2)0.0331 (6)
H10.250 (5)0.201 (4)0.044 (2)0.0330*
H3A0.062 (6)0.717 (4)0.346 (3)0.0500*
H3B0.461 (6)0.873 (5)0.338 (3)0.0500*
H3C0.417 (6)0.672 (4)0.440 (3)0.0500*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0391 (7)0.0235 (7)0.0283 (7)0.0061 (5)0.0152 (5)0.0048 (5)
O20.0557 (8)0.0314 (7)0.0341 (7)0.0032 (5)0.0253 (6)0.0051 (5)
C10.0303 (8)0.0293 (9)0.0264 (9)0.0095 (6)0.0123 (6)0.0089 (7)
C20.0290 (8)0.0252 (9)0.0261 (8)0.0074 (6)0.0089 (6)0.0063 (7)
C30.0411 (10)0.0256 (10)0.0303 (9)0.0074 (7)0.0133 (7)0.0017 (7)
Geometric parameters (Å, º) top
O1—C21.337 (2)C1—H10.96 (2)
O1—C31.452 (2)C3—H3A0.95 (2)
O2—C21.203 (2)C3—H3B0.95 (3)
C1—C21.488 (2)C3—H3C0.94 (2)
C1—C1i1.318 (2)
O1···C1ii3.375 (2)C3···O2viii3.416 (2)
O2···C1iii3.383 (2)C3···C3ix3.498 (3)
O2···C3iv3.394 (2)C3···O2iv3.394 (2)
O2···C2iii3.345 (2)C3···C1ii3.590 (3)
O2···C3v3.416 (2)C3···H3Avi2.92 (2)
O1···H3Avi2.83 (2)C3···H3Bix2.99 (3)
O1···H1vii2.65 (2)H1···O1vii2.65 (2)
O2···H3Bv2.48 (3)H1···O2i2.643 (19)
O2···H3C2.64 (2)H3A···O1iii2.83 (2)
O2···H3A2.62 (2)H3A···O22.62 (2)
O2···H1i2.643 (19)H3A···C3iii2.92 (2)
C1···O2vi3.383 (2)H3B···O2viii2.48 (3)
C1···O1ii3.375 (2)H3B···C3ix2.99 (3)
C1···C3ii3.590 (3)H3C···O22.64 (2)
C2···O2vi3.345 (2)H3C···H3Cx2.52 (3)
C2—O1—C3115.45 (12)O1—C3—H3A109.1 (14)
C1i—C1—C2120.71 (15)O1—C3—H3B105.3 (15)
O1—C2—O2124.02 (14)O1—C3—H3C109.9 (14)
O1—C2—C1111.02 (13)H3A—C3—H3B112 (2)
O2—C2—C1124.97 (15)H3A—C3—H3C112 (2)
C2—C1—H1115.4 (12)H3B—C3—H3C109 (2)
C1i—C1—H1123.9 (12)
C3—O1—C2—O20.1 (2)C1i—C1—C2—O24.2 (3)
C3—O1—C2—C1179.97 (14)C2—C1—C1i—C2i180
C1i—C1—C2—O1175.94 (15)
Symmetry codes: (i) x, y, z; (ii) x, y+1, z; (iii) x1, y, z; (iv) x, y+1, z+1; (v) x1, y1, z; (vi) x+1, y, z; (vii) x+1, y+1, z; (viii) x+1, y+1, z; (ix) x+1, y+2, z+1; (x) x+1, y+1, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C1—H1···O1vii0.96 (2)2.65 (2)3.603 (2)173.2 (14)
C3—H3B···O2viii0.95 (3)2.48 (3)3.416 (2)167 (2)
Symmetry codes: (vii) x+1, y+1, z; (viii) x+1, y+1, z.
 

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