In the
rac isomer mixture of the title compound, C
24H
26O
8, the molecules are weakly linked
via C—H
O and π–π interactions, forming a three-dimensional network.
Supporting information
CCDC reference: 287603
Key indicators
- Single-crystal X-ray study
- T = 292 K
- Mean (C-C) = 0.005 Å
- R factor = 0.065
- wR factor = 0.177
- Data-to-parameter ratio = 13.8
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.53 Ratio
PLAT230_ALERT_2_C Hirshfeld Test Diff for C9 - C13 .. 5.06 su
PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C20
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C14
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C15
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C18
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C23
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 5
PLAT360_ALERT_2_C Short C(sp3)-C(sp3) Bond C9 - C13 ... 1.43 Ang.
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
9 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
8 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
Compound (I) was synthesized according to the literature procedure of Wu et al. (1998). Single crystals suitable for X-ray diffraction were obtained by slow evaporation of an ethanol solution at room temperature.
All H atoms were located at idealized positions (methyl C—H = 0.96 Å, methylene C—H = 0.97 Å, methine C—H = 0.98 Å and aromatic C—H = 0.93 Å) and included in the refinement using the riding-model approximation, with Uiso(H) = 1.5Ueq(C) for methyl H atoms and Uiso(H) = 1.2Ueq(C) for the other H atoms.
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.
rac-Diethyl 2,3-bis(2-methoxybenzoyl)succinate
top
Crystal data top
C24H26O8 | F(000) = 936 |
Mr = 442.45 | Dx = 1.277 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 4946 reflections |
a = 7.651 (1) Å | θ = 2.4–21.7° |
b = 28.146 (4) Å | µ = 0.10 mm−1 |
c = 10.9770 (14) Å | T = 292 K |
β = 103.214 (2)° | Block, colorless |
V = 2301.2 (5) Å3 | 0.30 × 0.30 × 0.20 mm |
Z = 4 | |
Data collection top
Bruker SMART APEX CCD area-detector diffractometer | Rint = 0.030 |
Graphite monochromator | θmax = 25.0°, θmin = 2.0° |
ω scans | h = −8→9 |
16206 measured reflections | k = −33→33 |
4040 independent reflections | l = −12→13 |
2830 reflections with I > 2σ(I) | |
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)] = 0.065 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.177 | H-atom parameters constrained |
S = 1.09 | w = 1/[σ2(Fo2) + (0.0669P)2 + 1.0101P] where P = (Fo2 + 2Fc2)/3 |
4040 reflections | (Δ/σ)max < 0.001 |
293 parameters | Δρmax = 0.18 e Å−3 |
0 restraints | Δρmin = −0.21 e Å−3 |
Crystal data top
C24H26O8 | V = 2301.2 (5) Å3 |
Mr = 442.45 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 7.651 (1) Å | µ = 0.10 mm−1 |
b = 28.146 (4) Å | T = 292 K |
c = 10.9770 (14) Å | 0.30 × 0.30 × 0.20 mm |
β = 103.214 (2)° | |
Data collection top
Bruker SMART APEX CCD area-detector diffractometer | 2830 reflections with I > 2σ(I) |
16206 measured reflections | Rint = 0.030 |
4040 independent reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.065 | 0 restraints |
wR(F2) = 0.177 | H-atom parameters constrained |
S = 1.09 | Δρmax = 0.18 e Å−3 |
4040 reflections | Δρmin = −0.21 e Å−3 |
293 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 | 0.1573 (5) | 0.47264 (18) | 0.6946 (5) | 0.1269 (16) | |
H1A | 0.0990 | 0.4813 | 0.7601 | 0.190* | |
H1B | 0.1031 | 0.4443 | 0.6540 | 0.190* | |
H1C | 0.1445 | 0.4980 | 0.6346 | 0.190* | |
C2 | 0.4462 (4) | 0.50008 (11) | 0.8083 (3) | 0.0709 (8) | |
C3 | 0.3777 (5) | 0.54409 (13) | 0.8300 (3) | 0.0877 (10) | |
H3 | 0.2559 | 0.5504 | 0.8013 | 0.105* | |
C4 | 0.4898 (7) | 0.57846 (13) | 0.8940 (4) | 0.0984 (12) | |
H4 | 0.4428 | 0.6078 | 0.9087 | 0.118* | |
C5 | 0.6696 (7) | 0.57010 (13) | 0.9363 (4) | 0.0973 (12) | |
H5 | 0.7447 | 0.5937 | 0.9785 | 0.117* | |
C6 | 0.7374 (5) | 0.52684 (10) | 0.9159 (3) | 0.0793 (9) | |
H6 | 0.8594 | 0.5211 | 0.9460 | 0.095* | |
C7 | 0.6291 (4) | 0.49098 (10) | 0.8513 (3) | 0.0652 (7) | |
C8 | 0.7201 (4) | 0.44478 (10) | 0.8403 (3) | 0.0650 (7) | |
C9 | 0.6413 (4) | 0.40748 (9) | 0.7436 (3) | 0.0700 (8) | |
H9 | 0.5281 | 0.3983 | 0.7646 | 0.084* | |
C10 | 0.5861 (4) | 0.42674 (10) | 0.6128 (3) | 0.0655 (7) | |
C11 | 0.3753 (5) | 0.42202 (14) | 0.4190 (3) | 0.0912 (10) | |
H11A | 0.4550 | 0.4102 | 0.3687 | 0.109* | |
H11B | 0.3740 | 0.4564 | 0.4147 | 0.109* | |
C12 | 0.1940 (6) | 0.4034 (2) | 0.3711 (4) | 0.1414 (19) | |
H12A | 0.1980 | 0.3694 | 0.3688 | 0.212* | |
H12B | 0.1470 | 0.4155 | 0.2883 | 0.212* | |
H12C | 0.1180 | 0.4133 | 0.4250 | 0.212* | |
C13 | 0.7436 (4) | 0.36454 (10) | 0.7556 (3) | 0.0659 (8) | |
H13 | 0.8615 | 0.3747 | 0.7444 | 0.079* | |
C14 | 0.6872 (4) | 0.32635 (10) | 0.6581 (3) | 0.0631 (7) | |
C15 | 0.6810 (6) | 0.30119 (14) | 0.4522 (4) | 0.1003 (12) | |
H15A | 0.7179 | 0.2698 | 0.4846 | 0.120* | |
H15B | 0.5518 | 0.3010 | 0.4205 | 0.120* | |
C16 | 0.7687 (9) | 0.3130 (2) | 0.3527 (5) | 0.156 (2) | |
H16A | 0.7406 | 0.3452 | 0.3265 | 0.235* | |
H16B | 0.7273 | 0.2920 | 0.2832 | 0.235* | |
H16C | 0.8962 | 0.3097 | 0.3823 | 0.235* | |
C17 | 0.7839 (4) | 0.34207 (9) | 0.8842 (3) | 0.0616 (7) | |
C18 | 0.9645 (4) | 0.32303 (9) | 0.9425 (3) | 0.0633 (7) | |
C19 | 1.0010 (5) | 0.31416 (13) | 1.0678 (4) | 0.0977 (11) | |
H19 | 0.9116 | 0.3183 | 1.1118 | 0.117* | |
C20 | 1.1719 (8) | 0.29886 (17) | 1.1310 (5) | 0.1374 (19) | |
H20 | 1.1973 | 0.2936 | 1.2169 | 0.165* | |
C21 | 1.2995 (7) | 0.29178 (16) | 1.0658 (7) | 0.136 (2) | |
H21 | 1.4124 | 0.2811 | 1.1075 | 0.164* | |
C22 | 1.2667 (5) | 0.29990 (14) | 0.9415 (6) | 0.1132 (15) | |
H22 | 1.3574 | 0.2956 | 0.8987 | 0.136* | |
C23 | 1.0981 (4) | 0.31463 (11) | 0.8777 (4) | 0.0788 (10) | |
C24 | 1.1917 (6) | 0.32955 (19) | 0.6873 (5) | 0.149 (2) | |
H24A | 1.2424 | 0.3604 | 0.7104 | 0.224* | |
H24B | 1.1413 | 0.3287 | 0.5988 | 0.224* | |
H24C | 1.2839 | 0.3059 | 0.7086 | 0.224* | |
O1 | 0.3447 (3) | 0.46418 (8) | 0.7471 (2) | 0.0892 (7) | |
O2 | 0.8632 (3) | 0.43649 (8) | 0.9100 (3) | 0.1008 (8) | |
O3 | 0.6719 (3) | 0.45627 (8) | 0.5730 (2) | 0.0887 (7) | |
O4 | 0.4380 (3) | 0.40670 (7) | 0.54783 (18) | 0.0689 (5) | |
O5 | 0.6108 (3) | 0.29144 (8) | 0.6779 (2) | 0.0934 (7) | |
O6 | 0.7305 (3) | 0.33630 (7) | 0.5512 (2) | 0.0778 (6) | |
O7 | 0.6648 (3) | 0.33941 (8) | 0.9401 (2) | 0.0842 (7) | |
O8 | 1.0550 (3) | 0.32023 (12) | 0.7523 (3) | 0.1155 (10) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.064 (2) | 0.151 (4) | 0.158 (4) | 0.010 (2) | 0.011 (2) | −0.020 (3) |
C2 | 0.081 (2) | 0.0704 (18) | 0.0655 (19) | −0.0021 (16) | 0.0261 (16) | 0.0005 (15) |
C3 | 0.105 (3) | 0.085 (2) | 0.082 (2) | 0.017 (2) | 0.042 (2) | 0.0093 (19) |
C4 | 0.153 (4) | 0.068 (2) | 0.087 (3) | 0.011 (2) | 0.054 (3) | −0.0008 (19) |
C5 | 0.132 (4) | 0.068 (2) | 0.091 (3) | −0.010 (2) | 0.025 (3) | −0.0099 (18) |
C6 | 0.105 (3) | 0.0595 (18) | 0.072 (2) | −0.0098 (17) | 0.0187 (18) | −0.0029 (15) |
C7 | 0.080 (2) | 0.0579 (16) | 0.0605 (18) | −0.0029 (14) | 0.0217 (15) | −0.0018 (13) |
C8 | 0.0581 (18) | 0.0635 (16) | 0.073 (2) | −0.0101 (13) | 0.0142 (15) | −0.0065 (14) |
C9 | 0.0717 (19) | 0.0528 (15) | 0.078 (2) | −0.0088 (13) | 0.0027 (16) | −0.0011 (14) |
C10 | 0.0668 (18) | 0.0527 (15) | 0.077 (2) | −0.0038 (14) | 0.0164 (16) | −0.0035 (14) |
C11 | 0.105 (3) | 0.097 (2) | 0.067 (2) | −0.007 (2) | 0.009 (2) | 0.0126 (18) |
C12 | 0.110 (3) | 0.218 (6) | 0.080 (3) | −0.031 (4) | −0.010 (2) | 0.012 (3) |
C13 | 0.0661 (18) | 0.0640 (17) | 0.0712 (19) | 0.0110 (13) | 0.0230 (15) | −0.0039 (14) |
C14 | 0.0517 (16) | 0.0627 (17) | 0.077 (2) | 0.0047 (13) | 0.0192 (14) | −0.0051 (14) |
C15 | 0.109 (3) | 0.096 (3) | 0.099 (3) | −0.015 (2) | 0.029 (2) | −0.032 (2) |
C16 | 0.212 (6) | 0.171 (5) | 0.111 (4) | −0.059 (4) | 0.089 (4) | −0.059 (3) |
C17 | 0.0525 (16) | 0.0577 (15) | 0.078 (2) | 0.0026 (12) | 0.0215 (15) | −0.0020 (14) |
C18 | 0.0537 (16) | 0.0539 (15) | 0.081 (2) | 0.0045 (12) | 0.0132 (15) | 0.0032 (14) |
C19 | 0.092 (3) | 0.099 (3) | 0.097 (3) | 0.024 (2) | 0.011 (2) | 0.013 (2) |
C20 | 0.131 (4) | 0.125 (4) | 0.129 (4) | 0.049 (3) | −0.025 (3) | 0.016 (3) |
C21 | 0.077 (3) | 0.095 (3) | 0.208 (6) | 0.035 (2) | −0.026 (4) | −0.006 (4) |
C22 | 0.055 (2) | 0.087 (3) | 0.190 (5) | 0.0063 (18) | 0.012 (3) | −0.021 (3) |
C23 | 0.0459 (17) | 0.0651 (18) | 0.124 (3) | −0.0072 (13) | 0.0171 (19) | −0.0106 (18) |
C24 | 0.114 (4) | 0.164 (4) | 0.206 (6) | −0.025 (3) | 0.112 (4) | −0.018 (4) |
O1 | 0.0661 (14) | 0.0945 (16) | 0.1068 (18) | −0.0001 (12) | 0.0196 (12) | −0.0139 (13) |
O2 | 0.0651 (15) | 0.0953 (16) | 0.125 (2) | 0.0028 (12) | −0.0132 (14) | −0.0383 (14) |
O3 | 0.0940 (16) | 0.0773 (14) | 0.0969 (17) | −0.0206 (12) | 0.0258 (13) | 0.0072 (12) |
O4 | 0.0715 (13) | 0.0698 (12) | 0.0630 (13) | −0.0066 (10) | 0.0103 (10) | 0.0043 (9) |
O5 | 0.0889 (16) | 0.0853 (15) | 0.1082 (19) | −0.0327 (13) | 0.0273 (14) | −0.0078 (13) |
O6 | 0.0893 (15) | 0.0758 (13) | 0.0748 (14) | −0.0093 (11) | 0.0324 (12) | −0.0179 (11) |
O7 | 0.0616 (13) | 0.1065 (17) | 0.0926 (16) | 0.0100 (11) | 0.0346 (12) | 0.0121 (12) |
O8 | 0.0619 (15) | 0.177 (3) | 0.120 (2) | −0.0084 (15) | 0.0464 (16) | −0.0081 (19) |
Geometric parameters (Å, º) top
C1—O1 | 1.438 (4) | C13—C14 | 1.508 (4) |
C1—H1A | 0.9600 | C13—C17 | 1.513 (4) |
C1—H1B | 0.9600 | C13—H13 | 0.9800 |
C1—H1C | 0.9600 | C14—O5 | 1.189 (3) |
C2—O1 | 1.355 (4) | C14—O6 | 1.320 (3) |
C2—C3 | 1.387 (4) | C15—C16 | 1.445 (5) |
C2—C7 | 1.395 (4) | C15—O6 | 1.453 (4) |
C3—C4 | 1.375 (5) | C15—H15A | 0.9700 |
C3—H3 | 0.9300 | C15—H15B | 0.9700 |
C4—C5 | 1.368 (6) | C16—H16A | 0.9600 |
C4—H4 | 0.9300 | C16—H16B | 0.9600 |
C5—C6 | 1.362 (5) | C16—H16C | 0.9600 |
C5—H5 | 0.9300 | C17—O7 | 1.212 (3) |
C6—C7 | 1.393 (4) | C17—C18 | 1.484 (4) |
C6—H6 | 0.9300 | C18—C19 | 1.363 (5) |
C7—C8 | 1.493 (4) | C18—C23 | 1.392 (4) |
C8—O2 | 1.206 (3) | C19—C20 | 1.401 (6) |
C8—C9 | 1.517 (4) | C19—H19 | 0.9300 |
C9—C13 | 1.429 (4) | C20—C21 | 1.350 (8) |
C9—C10 | 1.503 (4) | C20—H20 | 0.9300 |
C9—H9 | 0.9800 | C21—C22 | 1.350 (7) |
C10—O3 | 1.201 (3) | C21—H21 | 0.9300 |
C10—O4 | 1.320 (3) | C22—C23 | 1.384 (5) |
C11—O4 | 1.451 (4) | C22—H22 | 0.9300 |
C11—C12 | 1.463 (5) | C23—O8 | 1.349 (4) |
C11—H11A | 0.9700 | C24—O8 | 1.419 (4) |
C11—H11B | 0.9700 | C24—H24A | 0.9600 |
C12—H12A | 0.9600 | C24—H24B | 0.9600 |
C12—H12B | 0.9600 | C24—H24C | 0.9600 |
C12—H12C | 0.9600 | | |
| | | |
O1—C1—H1A | 109.5 | C14—C13—C17 | 109.2 (2) |
O1—C1—H1B | 109.5 | C9—C13—H13 | 104.0 |
H1A—C1—H1B | 109.5 | C14—C13—H13 | 104.0 |
O1—C1—H1C | 109.5 | C17—C13—H13 | 104.0 |
H1A—C1—H1C | 109.5 | O5—C14—O6 | 124.9 (3) |
H1B—C1—H1C | 109.5 | O5—C14—C13 | 122.2 (3) |
O1—C2—C3 | 123.7 (3) | O6—C14—C13 | 113.0 (2) |
O1—C2—C7 | 116.6 (3) | C16—C15—O6 | 108.8 (3) |
C3—C2—C7 | 119.7 (3) | C16—C15—H15A | 109.9 |
C4—C3—C2 | 120.0 (4) | O6—C15—H15A | 109.9 |
C4—C3—H3 | 120.0 | C16—C15—H15B | 109.9 |
C2—C3—H3 | 120.0 | O6—C15—H15B | 109.9 |
C5—C4—C3 | 120.9 (3) | H15A—C15—H15B | 108.3 |
C5—C4—H4 | 119.5 | C15—C16—H16A | 109.5 |
C3—C4—H4 | 119.5 | C15—C16—H16B | 109.5 |
C6—C5—C4 | 119.3 (4) | H16A—C16—H16B | 109.5 |
C6—C5—H5 | 120.3 | C15—C16—H16C | 109.5 |
C4—C5—H5 | 120.3 | H16A—C16—H16C | 109.5 |
C5—C6—C7 | 121.8 (4) | H16B—C16—H16C | 109.5 |
C5—C6—H6 | 119.1 | O7—C17—C18 | 119.5 (3) |
C7—C6—H6 | 119.1 | O7—C17—C13 | 118.8 (3) |
C6—C7—C2 | 118.3 (3) | C18—C17—C13 | 121.6 (2) |
C6—C7—C8 | 116.0 (3) | C19—C18—C23 | 118.6 (3) |
C2—C7—C8 | 125.7 (3) | C19—C18—C17 | 117.2 (3) |
O2—C8—C7 | 119.3 (3) | C23—C18—C17 | 124.1 (3) |
O2—C8—C9 | 117.9 (3) | C18—C19—C20 | 120.6 (4) |
C7—C8—C9 | 122.8 (3) | C18—C19—H19 | 119.7 |
C13—C9—C10 | 114.9 (3) | C20—C19—H19 | 119.7 |
C13—C9—C8 | 113.5 (3) | C21—C20—C19 | 119.3 (5) |
C10—C9—C8 | 113.5 (2) | C21—C20—H20 | 120.3 |
C13—C9—H9 | 104.5 | C19—C20—H20 | 120.3 |
C10—C9—H9 | 104.5 | C22—C21—C20 | 121.4 (4) |
C8—C9—H9 | 104.5 | C22—C21—H21 | 119.3 |
O3—C10—O4 | 124.9 (3) | C20—C21—H21 | 119.3 |
O3—C10—C9 | 122.7 (3) | C21—C22—C23 | 119.9 (5) |
O4—C10—C9 | 112.4 (2) | C21—C22—H22 | 120.1 |
O4—C11—C12 | 108.6 (3) | C23—C22—H22 | 120.1 |
O4—C11—H11A | 110.0 | O8—C23—C22 | 122.2 (4) |
C12—C11—H11A | 110.0 | O8—C23—C18 | 117.7 (3) |
O4—C11—H11B | 110.0 | C22—C23—C18 | 120.1 (4) |
C12—C11—H11B | 110.0 | O8—C24—H24A | 109.5 |
H11A—C11—H11B | 108.4 | O8—C24—H24B | 109.5 |
C11—C12—H12A | 109.5 | H24A—C24—H24B | 109.5 |
C11—C12—H12B | 109.5 | O8—C24—H24C | 109.5 |
H12A—C12—H12B | 109.5 | H24A—C24—H24C | 109.5 |
C11—C12—H12C | 109.5 | H24B—C24—H24C | 109.5 |
H12A—C12—H12C | 109.5 | C2—O1—C1 | 118.8 (3) |
H12B—C12—H12C | 109.5 | C10—O4—C11 | 116.8 (2) |
C9—C13—C14 | 118.4 (2) | C14—O6—C15 | 116.4 (3) |
C9—C13—C17 | 115.5 (2) | C23—O8—C24 | 119.9 (3) |
| | | |
O1—C2—C3—C4 | 179.4 (3) | C17—C13—C14—O6 | −149.7 (2) |
C7—C2—C3—C4 | −0.1 (5) | C9—C13—C17—O7 | 44.1 (4) |
C2—C3—C4—C5 | 0.4 (5) | C14—C13—C17—O7 | −92.1 (3) |
C3—C4—C5—C6 | −0.8 (6) | C9—C13—C17—C18 | −136.3 (3) |
C4—C5—C6—C7 | 1.0 (5) | C14—C13—C17—C18 | 87.4 (3) |
C5—C6—C7—C2 | −0.7 (5) | O7—C17—C18—C19 | −16.0 (4) |
C5—C6—C7—C8 | −177.7 (3) | C13—C17—C18—C19 | 164.5 (3) |
O1—C2—C7—C6 | −179.3 (3) | O7—C17—C18—C23 | 165.2 (3) |
C3—C2—C7—C6 | 0.3 (4) | C13—C17—C18—C23 | −14.3 (4) |
O1—C2—C7—C8 | −2.7 (4) | C23—C18—C19—C20 | 2.7 (5) |
C3—C2—C7—C8 | 176.9 (3) | C17—C18—C19—C20 | −176.2 (3) |
C6—C7—C8—O2 | 18.1 (4) | C18—C19—C20—C21 | −1.7 (7) |
C2—C7—C8—O2 | −158.6 (3) | C19—C20—C21—C22 | 1.1 (8) |
C6—C7—C8—C9 | −161.3 (3) | C20—C21—C22—C23 | −1.7 (7) |
C2—C7—C8—C9 | 22.0 (5) | C21—C22—C23—O8 | −175.6 (4) |
O2—C8—C9—C13 | 5.1 (4) | C21—C22—C23—C18 | 2.7 (6) |
C7—C8—C9—C13 | −175.5 (3) | C19—C18—C23—O8 | 175.1 (3) |
O2—C8—C9—C10 | −128.6 (3) | C17—C18—C23—O8 | −6.1 (4) |
C7—C8—C9—C10 | 50.8 (4) | C19—C18—C23—C22 | −3.2 (5) |
C13—C9—C10—O3 | −94.4 (3) | C17—C18—C23—C22 | 175.5 (3) |
C8—C9—C10—O3 | 38.6 (4) | C3—C2—O1—C1 | 3.9 (5) |
C13—C9—C10—O4 | 84.0 (3) | C7—C2—O1—C1 | −176.5 (3) |
C8—C9—C10—O4 | −143.0 (3) | O3—C10—O4—C11 | −0.3 (4) |
C10—C9—C13—C14 | −42.0 (4) | C9—C10—O4—C11 | −178.6 (3) |
C8—C9—C13—C14 | −175.0 (3) | C12—C11—O4—C10 | −168.8 (3) |
C10—C9—C13—C17 | −174.0 (3) | O5—C14—O6—C15 | −0.6 (4) |
C8—C9—C13—C17 | 53.0 (4) | C13—C14—O6—C15 | 179.9 (3) |
C9—C13—C14—O5 | −104.0 (4) | C16—C15—O6—C14 | −168.7 (4) |
C17—C13—C14—O5 | 30.8 (4) | C22—C23—O8—C24 | −24.9 (5) |
C9—C13—C14—O6 | 75.5 (3) | C18—C23—O8—C24 | 156.8 (3) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C21—H21···O5i | 0.93 | 2.56 | 3.366 (5) | 146 |
C4—H4···O7ii | 0.93 | 2.50 | 3.323 (4) | 147 |
C11—H11B···O3iii | 0.97 | 2.49 | 3.448 (5) | 169 |
Symmetry codes: (i) x+1, −y+1/2, z+1/2; (ii) −x+1, −y+1, −z+2; (iii) −x+1, −y+1, −z+1. |
Experimental details
Crystal data |
Chemical formula | C24H26O8 |
Mr | 442.45 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 292 |
a, b, c (Å) | 7.651 (1), 28.146 (4), 10.9770 (14) |
β (°) | 103.214 (2) |
V (Å3) | 2301.2 (5) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.10 |
Crystal size (mm) | 0.30 × 0.30 × 0.20 |
|
Data collection |
Diffractometer | Bruker SMART APEX CCD area-detector diffractometer |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 16206, 4040, 2830 |
Rint | 0.030 |
(sin θ/λ)max (Å−1) | 0.595 |
|
Refinement |
R[F2 > 2σ(F2)], wR(F2), S | 0.065, 0.177, 1.09 |
No. of reflections | 4040 |
No. of parameters | 293 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.18, −0.21 |
Selected geometric parameters (Å, º) topC7—C8 | 1.493 (4) | C13—C14 | 1.508 (4) |
C8—C9 | 1.517 (4) | C13—C17 | 1.513 (4) |
C9—C13 | 1.429 (4) | C17—C18 | 1.484 (4) |
C9—C10 | 1.503 (4) | | |
| | | |
C7—C8—C9—C13 | −175.5 (3) | C8—C9—C13—C17 | 53.0 (4) |
C7—C8—C9—C10 | 50.8 (4) | C9—C13—C17—C18 | −136.3 (3) |
C8—C9—C13—C14 | −175.0 (3) | C13—C17—C18—C23 | −14.3 (4) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C21—H21···O5i | 0.93 | 2.56 | 3.366 (5) | 146 |
C4—H4···O7ii | 0.93 | 2.50 | 3.323 (4) | 147 |
C11—H11B···O3iii | 0.97 | 2.49 | 3.448 (5) | 169 |
Symmetry codes: (i) x+1, −y+1/2, z+1/2; (ii) −x+1, −y+1, −z+2; (iii) −x+1, −y+1, −z+1. |
We synthesized the title compound, a 2,3-disubstituted succinate derivative, (I), according to the literature method of Wu et al. (1998), ands report here its crystal structure.
The molecular structure of (I) is illustrated in Fig. 1 and selected bond lengths and torsion angles are given in Table 1. Chiral atoms C9 and C13 possess the same configuration, indicating that (I) is the rac isomer. The central C8—C9—C13—C17 chain is in a cis configuration with a torsion angle of 53.0 (4)°. Analysis with PLATON (Spek, 2003) shows that no classic hydrogen bonds exist in the molecular structure, although C—H···O hydrogen bonds and a π–π interaction are present, forming a three-dimensional network in the crystal (Fig. 2 and Table 2). A π–π interaction is observed between the benzene rings [C2–C7 and C2i–C7i; symmetry code: (i) −x,1 − y,2 − z] with a centroid–centroid distance of 3.696 (2) Å.