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The title compound, C
26H
30O
10, is the
meso isomer of a 2,3-disubstituted succinic acid derivative and has inversion symmetry. The crystal structure is stabilized by intermolecular C—H
π and π–π stacking interactions.
Supporting information
CCDC reference: 287682
Key indicators
- Single-crystal X-ray study
- T = 292 K
- Mean (C-C) = 0.002 Å
- R factor = 0.045
- wR factor = 0.132
- Data-to-parameter ratio = 12.9
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT230_ALERT_2_C Hirshfeld Test Diff for O4 - C11 .. 5.71 su
PLAT480_ALERT_4_C Long H...A H-Bond Reported H13B .. CG1 .. 2.90 Ang.
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
2 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
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
Compound (I) was synthesized as reported previously (Wu et al., 1997). Crystals of (I) appropriate for data collection were obtained from a methanol–ethyl acetate solution by slow evaporation.
The methyl H atoms were constrained to an ideal geometry, with C—H distances of 0.96 Å and Uiso(H) = 1.5Ueq(C), but each group was allowed to rotate freely about its C—C bond. All other H atoms were placed in geometrically idealized positions and constrained to ride on their parent atoms, with C—H distances of 0.93 Å for phenyl H and 0.97 Å for methene H, and with Uiso(H) = 1.2Ueq(C).
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.
(2RS,3SR)-Diethyl 2,3-bis(3,4-dimethoxybenzoyl)succinate
top
Crystal data top
C26H30O10 | Z = 1 |
Mr = 502.50 | F(000) = 266 |
Triclinic, P1 | Dx = 1.351 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 8.5045 (10) Å | Cell parameters from 2590 reflections |
b = 8.5868 (10) Å | θ = 2.8–25.2° |
c = 9.0850 (11) Å | µ = 0.10 mm−1 |
α = 80.306 (2)° | T = 292 K |
β = 75.645 (2)° | Block, colorless |
γ = 75.245 (2)° | 0.40 × 0.20 × 0.20 mm |
V = 617.60 (13) Å3 | |
Data collection top
Bruker SMART CCD area-detector diffractometer | 1851 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.014 |
Graphite monochromator | θmax = 25.0°, θmin = 2.3° |
ϕ and ω scans | h = −9→10 |
3501 measured reflections | k = −8→10 |
2140 independent reflections | l = −10→10 |
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)] = 0.046 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.133 | H-atom parameters constrained |
S = 1.06 | w = 1/[σ2(Fo2) + (0.075P)2 + 0.1199P] where P = (Fo2 + 2Fc2)/3 |
2140 reflections | (Δ/σ)max < 0.001 |
166 parameters | Δρmax = 0.29 e Å−3 |
0 restraints | Δρmin = −0.22 e Å−3 |
Crystal data top
C26H30O10 | γ = 75.245 (2)° |
Mr = 502.50 | V = 617.60 (13) Å3 |
Triclinic, P1 | Z = 1 |
a = 8.5045 (10) Å | Mo Kα radiation |
b = 8.5868 (10) Å | µ = 0.10 mm−1 |
c = 9.0850 (11) Å | T = 292 K |
α = 80.306 (2)° | 0.40 × 0.20 × 0.20 mm |
β = 75.645 (2)° | |
Data collection top
Bruker SMART CCD area-detector diffractometer | 1851 reflections with I > 2σ(I) |
3501 measured reflections | Rint = 0.014 |
2140 independent reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.046 | 0 restraints |
wR(F2) = 0.133 | H-atom parameters constrained |
S = 1.06 | Δρmax = 0.29 e Å−3 |
2140 reflections | Δρmin = −0.22 e Å−3 |
166 parameters | |
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 | |
C1 | 0.1862 (3) | 0.3223 (2) | 0.3486 (2) | 0.0682 (6) | |
H1A | 0.2946 | 0.2538 | 0.3194 | 0.102* | |
H1B | 0.1356 | 0.3547 | 0.2616 | 0.102* | |
H1C | 0.1181 | 0.2640 | 0.4277 | 0.102* | |
C2 | 0.2224 (3) | 0.8657 (2) | 0.5539 (2) | 0.0610 (5) | |
H2A | 0.1509 | 0.8745 | 0.6535 | 0.092* | |
H2B | 0.1828 | 0.9558 | 0.4841 | 0.092* | |
H2C | 0.3336 | 0.8661 | 0.5592 | 0.092* | |
C3 | 0.26736 (19) | 0.43624 (19) | 0.53013 (17) | 0.0410 (4) | |
C4 | 0.27992 (19) | 0.57737 (19) | 0.58281 (18) | 0.0415 (4) | |
C5 | 0.3491 (2) | 0.5628 (2) | 0.70841 (18) | 0.0447 (4) | |
H5 | 0.3594 | 0.6551 | 0.7427 | 0.054* | |
C6 | 0.40328 (19) | 0.41121 (19) | 0.78359 (18) | 0.0434 (4) | |
H6 | 0.4502 | 0.4027 | 0.8676 | 0.052* | |
C7 | 0.38818 (18) | 0.27226 (19) | 0.73467 (17) | 0.0401 (4) | |
C8 | 0.32020 (19) | 0.28753 (19) | 0.60581 (17) | 0.0415 (4) | |
H8 | 0.3109 | 0.1950 | 0.5713 | 0.050* | |
C9 | 0.4371 (2) | 0.1073 (2) | 0.81095 (19) | 0.0465 (4) | |
C10 | 0.5136 (2) | 0.07973 (19) | 0.95268 (18) | 0.0436 (4) | |
H10 | 0.4619 | 0.1696 | 1.0150 | 0.052* | |
C11 | 0.6994 (2) | 0.0729 (2) | 0.89667 (18) | 0.0460 (4) | |
C12 | 0.9123 (2) | 0.2176 (2) | 0.8534 (2) | 0.0600 (5) | |
H12A | 0.9273 | 0.2601 | 0.7462 | 0.072* | |
H12B | 0.9868 | 0.1119 | 0.8625 | 0.072* | |
C13 | 0.9488 (3) | 0.3280 (3) | 0.9419 (3) | 0.0713 (6) | |
H13A | 0.8618 | 0.4247 | 0.9484 | 0.107* | |
H13B | 1.0531 | 0.3558 | 0.8920 | 0.107* | |
H13C | 0.9551 | 0.2755 | 1.0429 | 0.107* | |
O1 | 0.20140 (16) | 0.46252 (14) | 0.40393 (14) | 0.0559 (4) | |
O2 | 0.22213 (15) | 0.71867 (14) | 0.50181 (14) | 0.0523 (3) | |
O3 | 0.4202 (2) | −0.01003 (16) | 0.76366 (17) | 0.0771 (5) | |
O4 | 0.79541 (18) | −0.04036 (18) | 0.83980 (19) | 0.0752 (5) | |
O5 | 0.74006 (15) | 0.20440 (15) | 0.91485 (16) | 0.0585 (4) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.1036 (16) | 0.0506 (11) | 0.0680 (12) | −0.0163 (10) | −0.0507 (11) | −0.0078 (9) |
C2 | 0.0833 (13) | 0.0362 (9) | 0.0668 (12) | −0.0115 (9) | −0.0234 (10) | −0.0066 (8) |
C3 | 0.0452 (8) | 0.0414 (9) | 0.0394 (8) | −0.0106 (7) | −0.0132 (6) | −0.0052 (6) |
C4 | 0.0437 (8) | 0.0382 (9) | 0.0427 (8) | −0.0100 (7) | −0.0086 (6) | −0.0044 (6) |
C5 | 0.0514 (9) | 0.0409 (9) | 0.0468 (9) | −0.0141 (7) | −0.0118 (7) | −0.0113 (7) |
C6 | 0.0476 (9) | 0.0445 (9) | 0.0422 (8) | −0.0109 (7) | −0.0146 (7) | −0.0080 (7) |
C7 | 0.0406 (8) | 0.0415 (9) | 0.0401 (8) | −0.0101 (7) | −0.0101 (6) | −0.0060 (6) |
C8 | 0.0468 (9) | 0.0386 (9) | 0.0439 (8) | −0.0124 (7) | −0.0132 (7) | −0.0079 (7) |
C9 | 0.0563 (10) | 0.0411 (9) | 0.0486 (9) | −0.0127 (7) | −0.0210 (7) | −0.0060 (7) |
C10 | 0.0526 (9) | 0.0384 (9) | 0.0453 (9) | −0.0101 (7) | −0.0194 (7) | −0.0060 (7) |
C11 | 0.0543 (10) | 0.0414 (9) | 0.0454 (9) | −0.0107 (8) | −0.0158 (7) | −0.0060 (7) |
C12 | 0.0504 (10) | 0.0639 (12) | 0.0672 (12) | −0.0193 (9) | −0.0063 (8) | −0.0106 (9) |
C13 | 0.0601 (12) | 0.0897 (16) | 0.0735 (13) | −0.0330 (11) | −0.0071 (10) | −0.0208 (11) |
O1 | 0.0821 (9) | 0.0417 (7) | 0.0549 (7) | −0.0129 (6) | −0.0375 (6) | −0.0025 (5) |
O2 | 0.0704 (8) | 0.0363 (6) | 0.0549 (7) | −0.0107 (5) | −0.0245 (6) | −0.0032 (5) |
O3 | 0.1342 (14) | 0.0440 (8) | 0.0783 (9) | −0.0249 (8) | −0.0691 (9) | 0.0007 (6) |
O4 | 0.0639 (9) | 0.0631 (9) | 0.1015 (11) | −0.0175 (7) | −0.0047 (8) | −0.0319 (8) |
O5 | 0.0489 (7) | 0.0517 (8) | 0.0805 (9) | −0.0163 (6) | −0.0134 (6) | −0.0159 (6) |
Geometric parameters (Å, º) top
C1—O1 | 1.426 (2) | C7—C8 | 1.403 (2) |
C1—H1A | 0.9600 | C7—C9 | 1.474 (2) |
C1—H1B | 0.9600 | C8—H8 | 0.9300 |
C1—H1C | 0.9600 | C9—O3 | 1.2129 (19) |
C2—O2 | 1.422 (2) | C9—C10 | 1.540 (2) |
C2—H2A | 0.9600 | C10—C11 | 1.525 (2) |
C2—H2B | 0.9600 | C10—C10i | 1.528 (3) |
C2—H2C | 0.9600 | C10—H10 | 0.9800 |
C3—O1 | 1.3592 (19) | C11—O4 | 1.198 (2) |
C3—C8 | 1.368 (2) | C11—O5 | 1.309 (2) |
C3—C4 | 1.413 (2) | C12—O5 | 1.458 (2) |
C4—O2 | 1.353 (2) | C12—C13 | 1.474 (3) |
C4—C5 | 1.382 (2) | C12—H12A | 0.9700 |
C5—C6 | 1.387 (2) | C12—H12B | 0.9700 |
C5—H5 | 0.9300 | C13—H13A | 0.9600 |
C6—C7 | 1.387 (2) | C13—H13B | 0.9600 |
C6—H6 | 0.9300 | C13—H13C | 0.9600 |
| | | |
O1—C1—H1A | 109.5 | C7—C8—H8 | 119.4 |
O1—C1—H1B | 109.5 | O3—C9—C7 | 121.36 (14) |
H1A—C1—H1B | 109.5 | O3—C9—C10 | 118.22 (14) |
O1—C1—H1C | 109.5 | C7—C9—C10 | 120.41 (13) |
H1A—C1—H1C | 109.5 | C11—C10—C10i | 109.95 (16) |
H1B—C1—H1C | 109.5 | C11—C10—C9 | 107.63 (13) |
O2—C2—H2A | 109.5 | C10i—C10—C9 | 109.94 (15) |
O2—C2—H2B | 109.5 | C11—C10—H10 | 109.8 |
H2A—C2—H2B | 109.5 | C10i—C10—H10 | 109.8 |
O2—C2—H2C | 109.5 | C9—C10—H10 | 109.8 |
H2A—C2—H2C | 109.5 | O4—C11—O5 | 124.53 (16) |
H2B—C2—H2C | 109.5 | O4—C11—C10 | 122.83 (15) |
O1—C3—C8 | 125.18 (14) | O5—C11—C10 | 112.63 (14) |
O1—C3—C4 | 115.11 (14) | O5—C12—C13 | 107.63 (15) |
C8—C3—C4 | 119.70 (14) | O5—C12—H12A | 110.2 |
O2—C4—C5 | 125.31 (14) | C13—C12—H12A | 110.2 |
O2—C4—C3 | 115.30 (14) | O5—C12—H12B | 110.2 |
C5—C4—C3 | 119.39 (15) | C13—C12—H12B | 110.2 |
C4—C5—C6 | 120.36 (14) | H12A—C12—H12B | 108.5 |
C4—C5—H5 | 119.8 | C12—C13—H13A | 109.5 |
C6—C5—H5 | 119.8 | C12—C13—H13B | 109.5 |
C7—C6—C5 | 120.65 (14) | H13A—C13—H13B | 109.5 |
C7—C6—H6 | 119.7 | C12—C13—H13C | 109.5 |
C5—C6—H6 | 119.7 | H13A—C13—H13C | 109.5 |
C6—C7—C8 | 118.77 (14) | H13B—C13—H13C | 109.5 |
C6—C7—C9 | 124.15 (14) | C3—O1—C1 | 116.38 (13) |
C8—C7—C9 | 117.08 (14) | C4—O2—C2 | 118.15 (13) |
C3—C8—C7 | 121.12 (14) | C11—O5—C12 | 117.54 (14) |
C3—C8—H8 | 119.4 | | |
| | | |
O1—C3—C4—O2 | 1.0 (2) | C8—C7—C9—C10 | 179.69 (14) |
C8—C3—C4—O2 | −179.04 (14) | O3—C9—C10—C11 | 95.47 (19) |
O1—C3—C4—C5 | −178.48 (14) | C7—C9—C10—C11 | −83.84 (18) |
C8—C3—C4—C5 | 1.5 (2) | O3—C9—C10—C10i | −24.3 (3) |
O2—C4—C5—C6 | 179.52 (14) | C7—C9—C10—C10i | 156.42 (17) |
C3—C4—C5—C6 | −1.0 (2) | C10i—C10—C11—O4 | 46.7 (2) |
C4—C5—C6—C7 | −0.4 (2) | C9—C10—C11—O4 | −73.1 (2) |
C5—C6—C7—C8 | 1.3 (2) | C10i—C10—C11—O5 | −134.67 (17) |
C5—C6—C7—C9 | −177.82 (15) | C9—C10—C11—O5 | 105.59 (15) |
O1—C3—C8—C7 | 179.42 (14) | C8—C3—O1—C1 | 0.4 (2) |
C4—C3—C8—C7 | −0.5 (2) | C4—C3—O1—C1 | −179.62 (16) |
C6—C7—C8—C3 | −0.9 (2) | C5—C4—O2—C2 | −4.0 (2) |
C9—C7—C8—C3 | 178.32 (14) | C3—C4—O2—C2 | 176.49 (14) |
C6—C7—C9—O3 | 179.54 (16) | O4—C11—O5—C12 | 3.8 (3) |
C8—C7—C9—O3 | 0.4 (3) | C10—C11—O5—C12 | −174.83 (15) |
C6—C7—C9—C10 | −1.2 (2) | C13—C12—O5—C11 | −154.78 (17) |
Symmetry code: (i) −x+1, −y, −z+2. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C13—H13B···Cg1ii | 0.96 | 2.90 | 3.820 | 162 |
Symmetry code: (ii) x−1, y, z. |
Experimental details
Crystal data |
Chemical formula | C26H30O10 |
Mr | 502.50 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 292 |
a, b, c (Å) | 8.5045 (10), 8.5868 (10), 9.0850 (11) |
α, β, γ (°) | 80.306 (2), 75.645 (2), 75.245 (2) |
V (Å3) | 617.60 (13) |
Z | 1 |
Radiation type | Mo Kα |
µ (mm−1) | 0.10 |
Crystal size (mm) | 0.40 × 0.20 × 0.20 |
|
Data collection |
Diffractometer | Bruker SMART CCD area-detector diffractometer |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 3501, 2140, 1851 |
Rint | 0.014 |
(sin θ/λ)max (Å−1) | 0.595 |
|
Refinement |
R[F2 > 2σ(F2)], wR(F2), S | 0.046, 0.133, 1.06 |
No. of reflections | 2140 |
No. of parameters | 166 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.29, −0.22 |
Selected geometric parameters (Å, º) topC9—C10 | 1.540 (2) | C10—C10i | 1.528 (3) |
C10—C11 | 1.525 (2) | | |
| | | |
O3—C9—C7 | 121.36 (14) | C11—C10—C10i | 109.95 (16) |
O3—C9—C10 | 118.22 (14) | C11—C10—C9 | 107.63 (13) |
C7—C9—C10 | 120.41 (13) | C10i—C10—C9 | 109.94 (15) |
| | | |
O3—C9—C10—C11 | 95.47 (19) | C7—C9—C10—C10i | 156.42 (17) |
C7—C9—C10—C11 | −83.84 (18) | C10i—C10—C11—O4 | 46.7 (2) |
O3—C9—C10—C10i | −24.3 (3) | C9—C10—C11—O4 | −73.1 (2) |
Symmetry code: (i) −x+1, −y, −z+2. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C13—H13B···Cg1ii | 0.96 | 2.90 | 3.820 | 162 |
Symmetry code: (ii) x−1, y, z. |
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1,4-Diketones are versatile intermediates for synthesis of some natural products consisting of cyclopentanone and the furan ring system (McMurry & Meiton, 1971; Ito et al., 1975, 1977). In the present paper, we report the crystal structure of the title compound, (I), which is a 1,4-diketone. The structure of a similar compound, (2RS,3SR)-diethyl 2,3-bis(3,4,5-trimethoxybenzoyl)succinate, has been reported previously (Meng & Wu, 2005).
The asymmetric unit of (I) contains one-half molecule with the other half generated by a centre of inversion (Fig. 1 and Table 1). The crystal structure is stabilized by C—H···π intermolecular interactions (Table 2). The Cg1 in Table 2 is the centroid of the benzene ring (C3–C8). A π–π stacking interaction is also observed, the Cg1···Cg1(1 − x, 1 − y, 1 − z) distance being 3.794 Å.