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organic compounds
The title compound, C17H16O5, was isolated from the plant Lindera poliantha. The cyclopentenedione and phenyl rings are connected by the central C3O fragment, which makes dihedral angles with these rings of 7.10 (6) and 16.24 (10)°, respectively.
Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805012833/hg6179sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536805012833/hg6179Isup2.hkl |
CCDC reference: 274423
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C) = 0.003 Å
- R factor = 0.054
- wR factor = 0.149
- Data-to-parameter ratio = 15.5
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT432_ALERT_2_C Short Inter X...Y Contact O1 .. C17 .. 3.01 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 1 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 0 ALERT type 4 Improvement, methodology, query or suggestion
Computing details top
Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 1997); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 2003).
4,5-Dimethoxy-2-(1-methoxy-3-phenylallylidine)cyclcopent-4-ene-1,3-dione top
Crystal data top
C17H16O5 | Z = 2 |
Mr = 300.30 | F(000) = 316 |
Triclinic, P1 | Dx = 1.326 Mg m−3 |
Hall symbol: -P 1 | Melting point = 348–349 K |
a = 7.380 (3) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 8.139 (3) Å | Cell parameters from 866 reflections |
c = 13.781 (5) Å | θ = 1.5–26.4° |
α = 78.224 (5)° | µ = 0.10 mm−1 |
β = 87.913 (6)° | T = 298 K |
γ = 68.280 (5)° | Block, pale yellow |
V = 752.1 (5) Å3 | 0.48 × 0.32 × 0.31 mm |
Data collection top
Bruker SMART APEX area-detector diffractometer | 3079 independent reflections |
Radiation source: fine-focus sealed tube | 2588 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.018 |
Detector resolution: 83.66 pixels mm-1 | θmax = 26.4°, θmin = 1.5° |
ω scans | h = −9→9 |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | k = −10→10 |
Tmin = 0.954, Tmax = 0.970 | l = −17→17 |
8035 measured 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)] = 0.054 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.149 | H-atom parameters constrained |
S = 1.06 | w = 1/[σ2(Fo2) + (0.0726P)2 + 0.1615P] where P = (Fo2 + 2Fc2)/3 |
3079 reflections | (Δ/σ)max < 0.001 |
199 parameters | Δρmax = 0.25 e Å−3 |
0 restraints | Δρmin = −0.18 e Å−3 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
x | y | z | Uiso*/Ueq | ||
O5 | 0.1501 (2) | 0.86176 (19) | 0.45597 (11) | 0.0786 (4) | |
O2 | 0.3657 (2) | 0.34985 (17) | 0.35326 (10) | 0.0732 (4) | |
O3 | 0.3419 (2) | 0.41823 (17) | 0.13734 (9) | 0.0685 (4) | |
O4 | 0.1808 (2) | 0.83244 (17) | 0.07031 (9) | 0.0709 (4) | |
O1 | 0.1117 (2) | 0.98182 (17) | 0.23672 (10) | 0.0775 (4) | |
C14 | 0.2564 (3) | 0.4710 (3) | 0.79101 (14) | 0.0721 (5) | |
H14A | 0.2460 | 0.5868 | 0.7949 | 0.087* | |
C13 | 0.2865 (3) | 0.3412 (4) | 0.87678 (15) | 0.0817 (6) | |
H13A | 0.2978 | 0.3697 | 0.9377 | 0.098* | |
C12 | 0.2999 (3) | 0.1710 (4) | 0.87271 (17) | 0.0821 (6) | |
H12A | 0.3199 | 0.0837 | 0.9307 | 0.098* | |
C11 | 0.2836 (3) | 0.1287 (3) | 0.78237 (17) | 0.0777 (6) | |
H11A | 0.2918 | 0.0130 | 0.7794 | 0.093* | |
C10 | 0.2549 (3) | 0.2584 (3) | 0.69604 (15) | 0.0689 (5) | |
H10A | 0.2446 | 0.2286 | 0.6354 | 0.083* | |
C9 | 0.2412 (3) | 0.4321 (3) | 0.69859 (13) | 0.0600 (5) | |
C8 | 0.2167 (3) | 0.5727 (3) | 0.60975 (13) | 0.0627 (5) | |
H8A | 0.1880 | 0.6894 | 0.6195 | 0.075* | |
C7 | 0.2313 (3) | 0.5509 (3) | 0.51644 (13) | 0.0594 (4) | |
H7A | 0.2569 | 0.4361 | 0.5045 | 0.071* | |
C6 | 0.2092 (3) | 0.6978 (2) | 0.43233 (13) | 0.0568 (4) | |
C2 | 0.2326 (2) | 0.6763 (2) | 0.33700 (12) | 0.0539 (4) | |
C3 | 0.3000 (3) | 0.5028 (2) | 0.30336 (13) | 0.0552 (4) | |
C4 | 0.2821 (3) | 0.5457 (2) | 0.19353 (12) | 0.0546 (4) | |
C5 | 0.2172 (3) | 0.7261 (2) | 0.16088 (12) | 0.0558 (4) | |
C1 | 0.1804 (3) | 0.8193 (2) | 0.24556 (13) | 0.0566 (4) | |
C15 | 0.2730 (4) | 0.9617 (3) | 0.43911 (18) | 0.0854 (7) | |
H15A | 0.2111 | 1.0743 | 0.4602 | 0.128* | |
H15B | 0.2969 | 0.9849 | 0.3697 | 0.128* | |
H15C | 0.3946 | 0.8939 | 0.4761 | 0.128* | |
C17 | 0.2678 (3) | 0.2756 (3) | 0.16193 (16) | 0.0752 (6) | |
H17A | 0.3185 | 0.1931 | 0.1180 | 0.113* | |
H17B | 0.1279 | 0.3259 | 0.1552 | 0.113* | |
H17C | 0.3075 | 0.2125 | 0.2291 | 0.113* | |
C16 | 0.1798 (4) | 0.7516 (3) | −0.01322 (14) | 0.0789 (6) | |
H16A | 0.1520 | 0.8424 | −0.0732 | 0.118* | |
H16B | 0.0815 | 0.6995 | −0.0058 | 0.118* | |
H16C | 0.3053 | 0.6591 | −0.0164 | 0.118* |
Atomic displacement parameters (Å2) top
U11 | U22 | U33 | U12 | U13 | U23 | |
O5 | 0.0925 (10) | 0.0650 (8) | 0.0822 (10) | −0.0300 (7) | 0.0262 (8) | −0.0264 (7) |
O2 | 0.1039 (11) | 0.0519 (7) | 0.0544 (7) | −0.0239 (7) | −0.0103 (7) | 0.0026 (6) |
O3 | 0.0897 (9) | 0.0600 (7) | 0.0543 (7) | −0.0269 (7) | 0.0133 (6) | −0.0118 (6) |
O4 | 0.1013 (10) | 0.0597 (8) | 0.0467 (7) | −0.0309 (7) | −0.0050 (6) | 0.0031 (6) |
O1 | 0.1115 (12) | 0.0506 (8) | 0.0680 (9) | −0.0301 (7) | −0.0164 (7) | −0.0032 (6) |
C14 | 0.0794 (13) | 0.0910 (15) | 0.0540 (11) | −0.0399 (11) | 0.0100 (9) | −0.0177 (10) |
C13 | 0.0891 (15) | 0.1100 (19) | 0.0498 (11) | −0.0432 (14) | 0.0050 (10) | −0.0125 (11) |
C12 | 0.0760 (14) | 0.0979 (17) | 0.0609 (12) | −0.0300 (12) | −0.0005 (10) | 0.0049 (11) |
C11 | 0.0764 (13) | 0.0774 (14) | 0.0742 (14) | −0.0282 (11) | 0.0024 (10) | −0.0051 (11) |
C10 | 0.0664 (12) | 0.0836 (14) | 0.0580 (11) | −0.0289 (10) | 0.0057 (9) | −0.0156 (10) |
C9 | 0.0525 (9) | 0.0794 (12) | 0.0501 (10) | −0.0272 (9) | 0.0069 (7) | −0.0130 (9) |
C8 | 0.0629 (11) | 0.0753 (12) | 0.0546 (10) | −0.0305 (9) | 0.0078 (8) | −0.0157 (9) |
C7 | 0.0626 (10) | 0.0638 (11) | 0.0497 (10) | −0.0226 (8) | −0.0001 (7) | −0.0086 (8) |
C6 | 0.0542 (9) | 0.0580 (10) | 0.0571 (10) | −0.0202 (8) | 0.0017 (7) | −0.0108 (8) |
C2 | 0.0588 (10) | 0.0531 (9) | 0.0484 (9) | −0.0223 (8) | −0.0026 (7) | −0.0034 (7) |
C3 | 0.0611 (10) | 0.0524 (9) | 0.0497 (9) | −0.0226 (8) | −0.0017 (7) | −0.0018 (7) |
C4 | 0.0612 (10) | 0.0538 (9) | 0.0472 (9) | −0.0225 (8) | 0.0033 (7) | −0.0049 (7) |
C5 | 0.0613 (10) | 0.0554 (10) | 0.0479 (9) | −0.0239 (8) | −0.0011 (7) | 0.0003 (7) |
C1 | 0.0634 (10) | 0.0510 (10) | 0.0560 (10) | −0.0253 (8) | −0.0055 (8) | −0.0027 (7) |
C15 | 0.0960 (17) | 0.0825 (15) | 0.0926 (17) | −0.0432 (13) | 0.0041 (13) | −0.0312 (13) |
C17 | 0.0995 (16) | 0.0570 (11) | 0.0698 (13) | −0.0290 (11) | 0.0034 (11) | −0.0143 (9) |
C16 | 0.1088 (17) | 0.0729 (13) | 0.0476 (10) | −0.0299 (12) | −0.0045 (10) | −0.0020 (9) |
Geometric parameters (Å, º) top
O1—C1 | 1.210 (2) | C10—H10A | 0.9300 |
O2—C3 | 1.219 (2) | C9—C8 | 1.461 (3) |
C4—C5 | 1.347 (2) | C8—C7 | 1.329 (3) |
C6—C2 | 1.357 (3) | C8—H8A | 0.9300 |
O5—C6 | 1.347 (2) | C7—C6 | 1.450 (3) |
O5—C15 | 1.412 (2) | C7—H7A | 0.9300 |
O3—C4 | 1.355 (2) | C2—C3 | 1.479 (2) |
O3—C17 | 1.434 (2) | C2—C1 | 1.482 (2) |
O4—C5 | 1.338 (2) | C3—C4 | 1.481 (2) |
O4—C16 | 1.439 (2) | C5—C1 | 1.482 (3) |
C14—C13 | 1.378 (3) | C15—H15A | 0.9600 |
C14—C9 | 1.391 (3) | C15—H15B | 0.9600 |
C14—H14A | 0.9300 | C15—H15C | 0.9600 |
C13—C12 | 1.365 (3) | C17—H17A | 0.9600 |
C13—H13A | 0.9300 | C17—H17B | 0.9600 |
C12—C11 | 1.378 (3) | C17—H17C | 0.9600 |
C12—H12A | 0.9300 | C16—H16A | 0.9600 |
C11—C10 | 1.384 (3) | C16—H16B | 0.9600 |
C11—H11A | 0.9300 | C16—H16C | 0.9600 |
C10—C9 | 1.387 (3) | ||
C6—O5—C15 | 119.51 (16) | C3—C2—C1 | 105.84 (14) |
C4—O3—C17 | 116.06 (14) | O2—C3—C2 | 128.47 (16) |
C5—O4—C16 | 118.16 (15) | O2—C3—C4 | 124.11 (17) |
C13—C14—C9 | 121.3 (2) | C2—C3—C4 | 107.37 (14) |
C13—C14—H14A | 119.4 | C5—C4—O3 | 126.81 (16) |
C9—C14—H14A | 119.4 | C5—C4—C3 | 109.51 (16) |
C12—C13—C14 | 120.3 (2) | O3—C4—C3 | 123.37 (15) |
C12—C13—H13A | 119.9 | O4—C5—C4 | 133.23 (17) |
C14—C13—H13A | 119.9 | O4—C5—C1 | 116.22 (15) |
C13—C12—C11 | 119.8 (2) | C4—C5—C1 | 110.54 (15) |
C13—C12—H12A | 120.1 | O1—C1—C2 | 129.35 (17) |
C11—C12—H12A | 120.1 | O1—C1—C5 | 123.86 (16) |
C12—C11—C10 | 120.0 (2) | C2—C1—C5 | 106.70 (14) |
C12—C11—H11A | 120.0 | O5—C15—H15A | 109.5 |
C10—C11—H11A | 120.0 | O5—C15—H15B | 109.5 |
C11—C10—C9 | 121.0 (2) | H15A—C15—H15B | 109.5 |
C11—C10—H10A | 119.5 | O5—C15—H15C | 109.5 |
C9—C10—H10A | 119.5 | H15A—C15—H15C | 109.5 |
C10—C9—C14 | 117.56 (19) | H15B—C15—H15C | 109.5 |
C10—C9—C8 | 123.40 (17) | O3—C17—H17A | 109.5 |
C14—C9—C8 | 119.02 (19) | O3—C17—H17B | 109.5 |
C7—C8—C9 | 126.58 (19) | H17A—C17—H17B | 109.5 |
C7—C8—H8A | 116.7 | O3—C17—H17C | 109.5 |
C9—C8—H8A | 116.7 | H17A—C17—H17C | 109.5 |
C8—C7—C6 | 123.03 (19) | H17B—C17—H17C | 109.5 |
C8—C7—H7A | 118.5 | O4—C16—H16A | 109.5 |
C6—C7—H7A | 118.5 | O4—C16—H16B | 109.5 |
O5—C6—C2 | 122.03 (16) | H16A—C16—H16B | 109.5 |
O5—C6—C7 | 114.04 (16) | O4—C16—H16C | 109.5 |
C2—C6—C7 | 123.79 (17) | H16A—C16—H16C | 109.5 |
C6—C2—C3 | 126.29 (15) | H16B—C16—H16C | 109.5 |
C6—C2—C1 | 127.67 (16) | ||
C9—C14—C13—C12 | −0.8 (3) | C1—C2—C3—C4 | −1.36 (18) |
C14—C13—C12—C11 | 0.2 (3) | C17—O3—C4—C5 | −134.1 (2) |
C13—C12—C11—C10 | 0.4 (3) | C17—O3—C4—C3 | 52.9 (2) |
C12—C11—C10—C9 | −0.3 (3) | O2—C3—C4—C5 | −175.79 (18) |
C11—C10—C9—C14 | −0.3 (3) | C2—C3—C4—C5 | 2.0 (2) |
C11—C10—C9—C8 | 178.15 (17) | O2—C3—C4—O3 | −1.7 (3) |
C13—C14—C9—C10 | 0.8 (3) | C2—C3—C4—O3 | 176.06 (16) |
C13—C14—C9—C8 | −177.69 (18) | C16—O4—C5—C4 | 11.0 (3) |
C10—C9—C8—C7 | −10.1 (3) | C16—O4—C5—C1 | −168.85 (16) |
C14—C9—C8—C7 | 168.34 (19) | O3—C4—C5—O4 | 4.6 (3) |
C9—C8—C7—C6 | −178.53 (16) | C3—C4—C5—O4 | 178.42 (18) |
C15—O5—C6—C2 | −66.7 (3) | O3—C4—C5—C1 | −175.59 (17) |
C15—O5—C6—C7 | 117.4 (2) | C3—C4—C5—C1 | −1.7 (2) |
C8—C7—C6—O5 | −7.4 (3) | C6—C2—C1—O1 | 1.9 (3) |
C8—C7—C6—C2 | 176.80 (18) | C3—C2—C1—O1 | 176.99 (19) |
O5—C6—C2—C3 | 178.78 (16) | C6—C2—C1—C5 | −174.68 (17) |
C7—C6—C2—C3 | −5.7 (3) | C3—C2—C1—C5 | 0.38 (18) |
O5—C6—C2—C1 | −7.1 (3) | O4—C5—C1—O1 | 3.9 (3) |
C7—C6—C2—C1 | 168.39 (16) | C4—C5—C1—O1 | −175.99 (18) |
C6—C2—C3—O2 | −8.6 (3) | O4—C5—C1—C2 | −179.28 (14) |
C1—C2—C3—O2 | 176.27 (18) | C4—C5—C1—C2 | 0.9 (2) |
C6—C2—C3—C4 | 173.79 (16) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C7—H7A···O2 | 0.93 | 2.35 | 2.976 (3) | 124 |
C8—H8A···O5 | 0.93 | 2.36 | 2.730 (3) | 103 |
C15—H15B···O1 | 0.96 | 2.34 | 3.022 (3) | 128 |
C16—H16C···O3 | 0.96 | 2.52 | 2.929 (3) | 106 |
C17—H17C···O2 | 0.96 | 2.36 | 2.992 (3) | 123 |
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