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The title mol­ecule, C16H18O6, lies on a crystallographic inversion centre which is located at the centre of the benzene ring. The dihedral angle between the benzene ring and the methyl 3-hydroxy­acrylate unit is 13.74 (6)°. Intra­molecular O—H...O hydrogen bonds are observed.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807006198/ci2272sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807006198/ci2272Isup2.hkl
Contains datablock I

CCDC reference: 640297

Key indicators

  • Single-crystal X-ray study
  • T = 299 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.049
  • wR factor = 0.160
  • Data-to-parameter ratio = 14.2

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT180_ALERT_3_C Check Cell Rounding: # of Values Ending with 0 = 3
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 1 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT-Plus (Bruker, 2001); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: PLATON.

Diethyl 3,3-dihydroxy-3,3'-(p-phenylene)diprop-2-enoate top
Crystal data top
C16H18O6Z = 1
Mr = 306.30F(000) = 162
Triclinic, P1Dx = 1.350 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 5.0183 (1) ÅCell parameters from 1806 reflections
b = 5.7002 (5) Åθ = 3.1–28.0°
c = 13.5102 (9) ŵ = 0.10 mm1
α = 102.178 (3)°T = 299 K
β = 94.324 (1)°Plate, colourless
γ = 90.083 (1)°0.30 × 0.20 × 0.06 mm
V = 376.63 (4) Å3
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer
1255 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.026
Graphite monochromatorθmax = 26.0°, θmin = 1.6°
φ and ω scansh = 66
3247 measured reflectionsk = 77
1472 independent reflectionsl = 1616
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)] = 0.049Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.160H atoms treated by a mixture of independent and constrained refinement
S = 1.04 w = 1/[σ2(Fo2) + (0.1042P)2 + 0.0476P]
where P = (Fo2 + 2Fc2)/3
1472 reflections(Δ/σ)max = 0.001
104 parametersΔρmax = 0.27 e Å3
0 restraintsΔρmin = 0.23 e Å3
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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 > σ(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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.8962 (2)0.5683 (2)0.29525 (10)0.0582 (4)
H1A1.012 (5)0.525 (4)0.2554 (18)0.084 (7)*
O21.2226 (2)0.2849 (2)0.18678 (9)0.0632 (4)
O31.2792 (2)0.0803 (2)0.22246 (9)0.0628 (4)
C10.5151 (3)0.6430 (3)0.42980 (11)0.0451 (4)
H1B0.52450.74010.38280.054*
C20.6762 (3)0.4426 (2)0.42307 (10)0.0401 (4)
C30.6587 (3)0.3008 (3)0.49447 (11)0.0456 (4)
H30.76540.16650.49120.055*
C40.8634 (3)0.3866 (3)0.34175 (11)0.0423 (4)
C50.9908 (3)0.1773 (3)0.31692 (12)0.0482 (4)
H50.96260.05650.35190.058*
C61.1707 (3)0.1375 (3)0.23666 (12)0.0497 (4)
C71.4520 (4)0.1459 (4)0.13951 (14)0.0657 (5)
H7A1.57500.26790.15370.079*
H7B1.55610.00650.13380.079*
C81.2924 (5)0.2379 (4)0.04322 (16)0.0848 (7)
H8A1.40920.28030.01060.127*
H8B1.17240.11630.02880.127*
H8C1.19140.37720.04860.127*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0675 (8)0.0494 (7)0.0689 (8)0.0123 (5)0.0246 (6)0.0310 (6)
O20.0780 (8)0.0563 (8)0.0646 (8)0.0097 (6)0.0272 (6)0.0261 (6)
O30.0774 (8)0.0546 (8)0.0642 (8)0.0207 (6)0.0279 (6)0.0223 (6)
C10.0518 (8)0.0383 (8)0.0500 (8)0.0017 (6)0.0071 (6)0.0193 (6)
C20.0416 (7)0.0351 (8)0.0444 (8)0.0035 (6)0.0025 (6)0.0104 (6)
C30.0496 (8)0.0364 (8)0.0542 (8)0.0068 (6)0.0081 (6)0.0162 (6)
C40.0433 (7)0.0394 (8)0.0466 (8)0.0031 (6)0.0024 (6)0.0149 (6)
C50.0573 (9)0.0397 (8)0.0513 (9)0.0016 (6)0.0133 (7)0.0150 (7)
C60.0555 (9)0.0456 (9)0.0513 (9)0.0034 (7)0.0085 (7)0.0158 (7)
C70.0719 (11)0.0685 (12)0.0625 (11)0.0236 (9)0.0221 (9)0.0211 (9)
C80.0980 (16)0.0827 (15)0.0722 (13)0.0187 (12)0.0102 (11)0.0115 (11)
Geometric parameters (Å, º) top
O1—C41.3358 (18)C3—H30.93
O1—H1A0.82 (3)C4—C51.346 (2)
O2—C61.2218 (19)C5—C61.445 (2)
O3—C61.339 (2)C5—H50.93
O3—C71.455 (2)C7—C81.471 (3)
C1—C3i1.381 (2)C7—H7A0.97
C1—C21.392 (2)C7—H7B0.97
C1—H1B0.93C8—H8A0.96
C2—C31.390 (2)C8—H8B0.96
C2—C41.483 (2)C8—H8C0.96
C3—C1i1.381 (2)
C4—O1—H1A105.6 (17)C6—C5—H5119.5
C6—O3—C7117.62 (13)O2—C6—O3122.71 (15)
C3i—C1—C2120.72 (13)O2—C6—C5124.55 (15)
C3i—C1—H1B119.6O3—C6—C5112.74 (13)
C2—C1—H1B119.6O3—C7—C8110.53 (16)
C3—C2—C1118.47 (14)O3—C7—H7A109.5
C3—C2—C4121.63 (14)C8—C7—H7A109.5
C1—C2—C4119.89 (13)O3—C7—H7B109.5
C1i—C3—C2120.81 (14)C8—C7—H7B109.5
C1i—C3—H3119.6H7A—C7—H7B108.1
C2—C3—H3119.6C7—C8—H8A109.5
O1—C4—C5122.69 (14)C7—C8—H8B109.5
O1—C4—C2112.84 (13)H8A—C8—H8B109.5
C5—C4—C2124.47 (14)C7—C8—H8C109.5
C4—C5—C6120.95 (15)H8A—C8—H8C109.5
C4—C5—H5119.5H8B—C8—H8C109.5
C3i—C1—C2—C30.2 (2)O1—C4—C5—C60.6 (2)
C3i—C1—C2—C4179.44 (12)C2—C4—C5—C6179.85 (12)
C1—C2—C3—C1i0.2 (2)C7—O3—C6—O24.0 (3)
C4—C2—C3—C1i179.43 (12)C7—O3—C6—C5176.49 (13)
C3—C2—C4—O1165.88 (13)C4—C5—C6—O20.5 (3)
C1—C2—C4—O113.36 (19)C4—C5—C6—O3179.98 (14)
C3—C2—C4—C513.5 (2)C6—O3—C7—C883.8 (2)
C1—C2—C4—C5167.30 (14)
Symmetry code: (i) x+1, y+1, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1A···O20.82 (3)1.87 (3)2.6098 (16)149 (2)
 

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