4,5-Dimeth­oxy-2-(1-meth­oxy-3-phenyl­allyl­idene)­cyclopent-4-ene-1,3-dione (meth­yl linderone)

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.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](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

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Computing details

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

Crystal data

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) Å^3	0.48 × 0.32 × 0.31 mm

Data collection

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

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.054	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.149	H-atom parameters constrained
S = 1.06	w = 1/[σ^2(Fo^2) + (0.0726P)^2 + 0.1615P] where P = (Fo^2 + 2Fc^2)/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 (Ų)

	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 (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

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)

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