The title molecule, C
16H
18O
6, 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
CCDC reference: 640297
Key indicators
- Single-crystal X-ray study
- T = 299 K
- Mean (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
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
C16H18O6 | Z = 1 |
Mr = 306.30 | F(000) = 162 |
Triclinic, P1 | Dx = 1.350 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 5.0183 (1) Å | Cell parameters from 1806 reflections |
b = 5.7002 (5) Å | θ = 3.1–28.0° |
c = 13.5102 (9) Å | µ = 0.10 mm−1 |
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 tube | Rint = 0.026 |
Graphite monochromator | θmax = 26.0°, θmin = 1.6° |
φ and ω scans | h = −6→6 |
3247 measured reflections | k = −7→7 |
1472 independent reflections | l = −16→16 |
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)] = 0.049 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.160 | H 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 parameters | Δρmax = 0.27 e Å−3 |
0 restraints | Δρmin = −0.23 e Å−3 |
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 | x | y | z | Uiso*/Ueq | |
O1 | 0.8962 (2) | 0.5683 (2) | 0.29525 (10) | 0.0582 (4) | |
H1A | 1.012 (5) | 0.525 (4) | 0.2554 (18) | 0.084 (7)* | |
O2 | 1.2226 (2) | 0.2849 (2) | 0.18678 (9) | 0.0632 (4) | |
O3 | 1.2792 (2) | −0.0803 (2) | 0.22246 (9) | 0.0628 (4) | |
C1 | 0.5151 (3) | 0.6430 (3) | 0.42980 (11) | 0.0451 (4) | |
H1B | 0.5245 | 0.7401 | 0.3828 | 0.054* | |
C2 | 0.6762 (3) | 0.4426 (2) | 0.42307 (10) | 0.0401 (4) | |
C3 | 0.6587 (3) | 0.3008 (3) | 0.49447 (11) | 0.0456 (4) | |
H3 | 0.7654 | 0.1665 | 0.4912 | 0.055* | |
C4 | 0.8634 (3) | 0.3866 (3) | 0.34175 (11) | 0.0423 (4) | |
C5 | 0.9908 (3) | 0.1773 (3) | 0.31692 (12) | 0.0482 (4) | |
H5 | 0.9626 | 0.0565 | 0.3519 | 0.058* | |
C6 | 1.1707 (3) | 0.1375 (3) | 0.23666 (12) | 0.0497 (4) | |
C7 | 1.4520 (4) | −0.1459 (4) | 0.13951 (14) | 0.0657 (5) | |
H7A | 1.5750 | −0.2679 | 0.1537 | 0.079* | |
H7B | 1.5561 | −0.0065 | 0.1338 | 0.079* | |
C8 | 1.2924 (5) | −0.2379 (4) | 0.04322 (16) | 0.0848 (7) | |
H8A | 1.4092 | −0.2803 | −0.0106 | 0.127* | |
H8B | 1.1724 | −0.1163 | 0.0288 | 0.127* | |
H8C | 1.1914 | −0.3772 | 0.0486 | 0.127* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0675 (8) | 0.0494 (7) | 0.0689 (8) | 0.0123 (5) | 0.0246 (6) | 0.0310 (6) |
O2 | 0.0780 (8) | 0.0563 (8) | 0.0646 (8) | 0.0097 (6) | 0.0272 (6) | 0.0261 (6) |
O3 | 0.0774 (8) | 0.0546 (8) | 0.0642 (8) | 0.0207 (6) | 0.0279 (6) | 0.0223 (6) |
C1 | 0.0518 (8) | 0.0383 (8) | 0.0500 (8) | 0.0017 (6) | 0.0071 (6) | 0.0193 (6) |
C2 | 0.0416 (7) | 0.0351 (8) | 0.0444 (8) | −0.0035 (6) | 0.0025 (6) | 0.0104 (6) |
C3 | 0.0496 (8) | 0.0364 (8) | 0.0542 (8) | 0.0068 (6) | 0.0081 (6) | 0.0162 (6) |
C4 | 0.0433 (7) | 0.0394 (8) | 0.0466 (8) | −0.0031 (6) | 0.0024 (6) | 0.0149 (6) |
C5 | 0.0573 (9) | 0.0397 (8) | 0.0513 (9) | 0.0016 (6) | 0.0133 (7) | 0.0150 (7) |
C6 | 0.0555 (9) | 0.0456 (9) | 0.0513 (9) | 0.0034 (7) | 0.0085 (7) | 0.0158 (7) |
C7 | 0.0719 (11) | 0.0685 (12) | 0.0625 (11) | 0.0236 (9) | 0.0221 (9) | 0.0211 (9) |
C8 | 0.0980 (16) | 0.0827 (15) | 0.0722 (13) | 0.0187 (12) | 0.0102 (11) | 0.0115 (11) |
Geometric parameters (Å, º) top
O1—C4 | 1.3358 (18) | C3—H3 | 0.93 |
O1—H1A | 0.82 (3) | C4—C5 | 1.346 (2) |
O2—C6 | 1.2218 (19) | C5—C6 | 1.445 (2) |
O3—C6 | 1.339 (2) | C5—H5 | 0.93 |
O3—C7 | 1.455 (2) | C7—C8 | 1.471 (3) |
C1—C3i | 1.381 (2) | C7—H7A | 0.97 |
C1—C2 | 1.392 (2) | C7—H7B | 0.97 |
C1—H1B | 0.93 | C8—H8A | 0.96 |
C2—C3 | 1.390 (2) | C8—H8B | 0.96 |
C2—C4 | 1.483 (2) | C8—H8C | 0.96 |
C3—C1i | 1.381 (2) | | |
| | | |
C4—O1—H1A | 105.6 (17) | C6—C5—H5 | 119.5 |
C6—O3—C7 | 117.62 (13) | O2—C6—O3 | 122.71 (15) |
C3i—C1—C2 | 120.72 (13) | O2—C6—C5 | 124.55 (15) |
C3i—C1—H1B | 119.6 | O3—C6—C5 | 112.74 (13) |
C2—C1—H1B | 119.6 | O3—C7—C8 | 110.53 (16) |
C3—C2—C1 | 118.47 (14) | O3—C7—H7A | 109.5 |
C3—C2—C4 | 121.63 (14) | C8—C7—H7A | 109.5 |
C1—C2—C4 | 119.89 (13) | O3—C7—H7B | 109.5 |
C1i—C3—C2 | 120.81 (14) | C8—C7—H7B | 109.5 |
C1i—C3—H3 | 119.6 | H7A—C7—H7B | 108.1 |
C2—C3—H3 | 119.6 | C7—C8—H8A | 109.5 |
O1—C4—C5 | 122.69 (14) | C7—C8—H8B | 109.5 |
O1—C4—C2 | 112.84 (13) | H8A—C8—H8B | 109.5 |
C5—C4—C2 | 124.47 (14) | C7—C8—H8C | 109.5 |
C4—C5—C6 | 120.95 (15) | H8A—C8—H8C | 109.5 |
C4—C5—H5 | 119.5 | H8B—C8—H8C | 109.5 |
| | | |
C3i—C1—C2—C3 | −0.2 (2) | O1—C4—C5—C6 | −0.6 (2) |
C3i—C1—C2—C4 | −179.44 (12) | C2—C4—C5—C6 | −179.85 (12) |
C1—C2—C3—C1i | 0.2 (2) | C7—O3—C6—O2 | −4.0 (3) |
C4—C2—C3—C1i | 179.43 (12) | C7—O3—C6—C5 | 176.49 (13) |
C3—C2—C4—O1 | −165.88 (13) | C4—C5—C6—O2 | 0.5 (3) |
C1—C2—C4—O1 | 13.36 (19) | C4—C5—C6—O3 | −179.98 (14) |
C3—C2—C4—C5 | 13.5 (2) | C6—O3—C7—C8 | −83.8 (2) |
C1—C2—C4—C5 | −167.30 (14) | | |
Symmetry code: (i) −x+1, −y+1, −z+1. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1A···O2 | 0.82 (3) | 1.87 (3) | 2.6098 (16) | 149 (2) |