Dimethyl fumarate, C
6H
8O
4, 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
1) lattice planes.
Supporting information
CCDC reference: 239304
Key indicators
- Single-crystal X-ray study
- T = 150 K
- Mean (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
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.
Crystal data top
C6H8O4 | Z = 1 |
Mr = 144.12 | F(000) = 76 |
Triclinic, P1 | Quoted _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 1 | Dx = 1.429 Mg m−3 |
a = 3.8680 (14) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 5.643 (2) Å | Cell parameters from 530 reflections |
c = 8.364 (3) Å | θ = 2.0–25.0° |
α = 100.843 (16)° | µ = 0.12 mm−1 |
β = 100.289 (18)° | T = 150 K |
γ = 105.706 (14)° | Irregular block, colourless |
V = 167.44 (11) Å3 | 0.3 × 0.2 × 0.2 mm |
Data collection top
Nonius KappaCCD area-detector diffractometer | 542 reflections with I > 2σ(I) |
Radiation source: Rotating Anode | Rint = 0.037 |
Graphite monochromator | θmax = 25.2°, θmin = 2.6° |
Detector resolution: 18.4 pixels mm-1 | h = −4→3 |
φ scans and ω scans with κ offset | k = −6→6 |
1315 measured reflections | l = −9→10 |
597 independent reflections | |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.045 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.122 | Only 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 parameters | Δρmax = 0.24 e Å−3 |
0 restraints | Δρmin = −0.26 e Å−3 |
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 | x | y | z | Uiso*/Ueq | |
O1 | 0.2939 (3) | 0.53163 (19) | 0.19453 (13) | 0.0304 (4) | |
O2 | −0.0683 (3) | 0.2238 (2) | 0.28160 (14) | 0.0411 (4) | |
C1 | 0.0993 (4) | 0.1212 (3) | 0.02180 (18) | 0.0276 (5) | |
C2 | 0.0935 (4) | 0.2914 (3) | 0.17973 (18) | 0.0267 (5) | |
C3 | 0.3066 (5) | 0.7139 (3) | 0.3450 (2) | 0.0331 (6) | |
H1 | 0.250 (5) | 0.201 (4) | −0.044 (2) | 0.0330* | |
H3A | 0.062 (6) | 0.717 (4) | 0.346 (3) | 0.0500* | |
H3B | 0.461 (6) | 0.873 (5) | 0.338 (3) | 0.0500* | |
H3C | 0.417 (6) | 0.672 (4) | 0.440 (3) | 0.0500* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0391 (7) | 0.0235 (7) | 0.0283 (7) | 0.0061 (5) | 0.0152 (5) | 0.0048 (5) |
O2 | 0.0557 (8) | 0.0314 (7) | 0.0341 (7) | 0.0032 (5) | 0.0253 (6) | 0.0051 (5) |
C1 | 0.0303 (8) | 0.0293 (9) | 0.0264 (9) | 0.0095 (6) | 0.0123 (6) | 0.0089 (7) |
C2 | 0.0290 (8) | 0.0252 (9) | 0.0261 (8) | 0.0074 (6) | 0.0089 (6) | 0.0063 (7) |
C3 | 0.0411 (10) | 0.0256 (10) | 0.0303 (9) | 0.0074 (7) | 0.0133 (7) | 0.0017 (7) |
Geometric parameters (Å, º) top
O1—C2 | 1.337 (2) | C1—H1 | 0.96 (2) |
O1—C3 | 1.452 (2) | C3—H3A | 0.95 (2) |
O2—C2 | 1.203 (2) | C3—H3B | 0.95 (3) |
C1—C2 | 1.488 (2) | C3—H3C | 0.94 (2) |
C1—C1i | 1.318 (2) | | |
| | | |
O1···C1ii | 3.375 (2) | C3···O2viii | 3.416 (2) |
O2···C1iii | 3.383 (2) | C3···C3ix | 3.498 (3) |
O2···C3iv | 3.394 (2) | C3···O2iv | 3.394 (2) |
O2···C2iii | 3.345 (2) | C3···C1ii | 3.590 (3) |
O2···C3v | 3.416 (2) | C3···H3Avi | 2.92 (2) |
O1···H3Avi | 2.83 (2) | C3···H3Bix | 2.99 (3) |
O1···H1vii | 2.65 (2) | H1···O1vii | 2.65 (2) |
O2···H3Bv | 2.48 (3) | H1···O2i | 2.643 (19) |
O2···H3C | 2.64 (2) | H3A···O1iii | 2.83 (2) |
O2···H3A | 2.62 (2) | H3A···O2 | 2.62 (2) |
O2···H1i | 2.643 (19) | H3A···C3iii | 2.92 (2) |
C1···O2vi | 3.383 (2) | H3B···O2viii | 2.48 (3) |
C1···O1ii | 3.375 (2) | H3B···C3ix | 2.99 (3) |
C1···C3ii | 3.590 (3) | H3C···O2 | 2.64 (2) |
C2···O2vi | 3.345 (2) | H3C···H3Cx | 2.52 (3) |
| | | |
C2—O1—C3 | 115.45 (12) | O1—C3—H3A | 109.1 (14) |
C1i—C1—C2 | 120.71 (15) | O1—C3—H3B | 105.3 (15) |
O1—C2—O2 | 124.02 (14) | O1—C3—H3C | 109.9 (14) |
O1—C2—C1 | 111.02 (13) | H3A—C3—H3B | 112 (2) |
O2—C2—C1 | 124.97 (15) | H3A—C3—H3C | 112 (2) |
C2—C1—H1 | 115.4 (12) | H3B—C3—H3C | 109 (2) |
C1i—C1—H1 | 123.9 (12) | | |
| | | |
C3—O1—C2—O2 | −0.1 (2) | C1i—C1—C2—O2 | 4.2 (3) |
C3—O1—C2—C1 | −179.97 (14) | C2—C1—C1i—C2i | 180 |
C1i—C1—C2—O1 | −175.94 (15) | | |
Symmetry codes: (i) −x, −y, −z; (ii) −x, −y+1, −z; (iii) x−1, y, z; (iv) −x, −y+1, −z+1; (v) x−1, y−1, 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···A | D—H | H···A | D···A | D—H···A |
C1—H1···O1vii | 0.96 (2) | 2.65 (2) | 3.603 (2) | 173.2 (14) |
C3—H3B···O2viii | 0.95 (3) | 2.48 (3) | 3.416 (2) | 167 (2) |
Symmetry codes: (vii) −x+1, −y+1, −z; (viii) x+1, y+1, z. |