(2E,5E)-2,5-Bis(3,4,5-trimethoxy-benzyl-idene)cyclo-penta-none.

The title compound, C(25)H(28)O(7), was prepared by the base-catalysed reaction of 3,4,5-trimethoxy-benzaldehyde with cyclo-penta-none. The mol-ecule has crystallographic twofold rotation symmetry and adopts an E-configuration about the central olefinic bonds. The two benzene rings and the central cyclo-penta-none ring are almost coplanar [dihedral angle = 4.7 (2)°].

Related literature

For background literature, see: Guilford et al. (1999 ▶); Xue et al. (2008 ▶); Wu et al. (2008 ▶); Das et al. (2008 ▶). For related crystal structures, see: Sun & Cui (2007 ▶); Du et al. (2007 ▶); Wei et al. (2008 ▶).

Experimental

Crystal data

C25H28O7

M = 440.47

Monoclinic,

a = 18.573 (4) Å

b = 15.231 (3) Å

c = 8.8460 (18) Å

β = 113.99 (3)°

V = 2286.2 (10) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 293 (2) K

0.30 × 0.20 × 0.20 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

Absorption correction: ψ scan (North et al., 1968 ▶) T min = 0.973, T max = 0.982

2123 measured reflections

2058 independent reflections

1422 reflections with I > 2σ(I)

R int = 0.048

3 standard reflections every 200 reflections intensity decay: none

Refinement

R[F 2 > 2σ(F 2)] = 0.055

wR(F 2) = 0.164

S = 1.00

2058 reflections

146 parameters

H-atom parameters constrained

Δρmax = 0.21 e Å−3

Δρmin = −0.27 e Å−3

Data collection: CAD-4 Software (Enraf–Nonius, 1989 ▶); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808029474/fj2151sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808029474/fj2151Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C25H28O7	F(000) = 936
Mr = 440.47	Dx = 1.280 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 25 reflections
a = 18.573 (4) Å	θ = 10–13°
b = 15.231 (3) Å	µ = 0.09 mm−1
c = 8.8460 (18) Å	T = 293 K
β = 113.99 (3)°	Block, yellow
V = 2286.2 (10) Å3	0.30 × 0.20 × 0.20 mm
Z = 4

Enraf–Nonius CAD-4 diffractometer	1422 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.048
graphite	θmax = 25.2°, θmin = 1.8°
ω/2θ scans	h = −22→20
Absorption correction: ψ scan (North et al., 1968)	k = 0→18
Tmin = 0.973, Tmax = 0.982	l = 0→10
2123 measured reflections	3 standard reflections every 200 reflections
2058 independent reflections	intensity decay: none

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)] = 0.055	Hydrogen site location: difference Fourier map
wR(F2) = 0.164	H-atom parameters constrained
S = 1.00	w = 1/[σ2(Fo2) + (0.080P)2 + 2.P] where P = (Fo2 + 2Fc2)/3
2058 reflections	(Δ/σ)max < 0.001
146 parameters	Δρmax = 0.21 e Å−3
0 restraints	Δρmin = −0.27 e Å−3

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.

	x	y	z	Uiso*/Ueq
O1	0.5000	0.43398 (16)	0.2500	0.0707 (8)
C1	0.5000	0.3537 (2)	0.2500	0.0510 (8)
C2	0.47174 (14)	0.29645 (15)	0.3510 (3)	0.0480 (6)
O2	0.36310 (14)	0.07554 (11)	0.6941 (3)	0.0806 (7)
O3	0.32676 (10)	0.18198 (11)	0.89316 (19)	0.0592 (5)
C3	0.47864 (15)	0.20225 (14)	0.3086 (3)	0.0512 (6)
H3A	0.4268	0.1760	0.2546	0.061*
H3B	0.5085	0.1690	0.4080	0.061*
O4	0.33734 (12)	0.35568 (11)	0.8758 (2)	0.0683 (6)
C4	0.44589 (14)	0.33133 (16)	0.4587 (3)	0.0517 (6)
H4A	0.4489	0.3922	0.4665	0.062*
C5	0.41371 (14)	0.28904 (15)	0.5662 (3)	0.0473 (6)
C6	0.39179 (15)	0.34335 (15)	0.6677 (3)	0.0526 (6)
H6A	0.3979	0.4038	0.6648	0.063*
C7	0.36086 (14)	0.30734 (16)	0.7728 (3)	0.0504 (6)
C8	0.35313 (13)	0.21799 (15)	0.7816 (3)	0.0478 (6)
C9	0.37410 (15)	0.16327 (15)	0.6797 (3)	0.0542 (6)
C10	0.40400 (15)	0.19887 (16)	0.5729 (3)	0.0555 (6)
H10A	0.4177	0.1620	0.5050	0.067*
C11	0.3772 (3)	0.01797 (19)	0.5835 (5)	0.1075 (13)
H11A	0.3679	−0.0414	0.6071	0.161*
H11B	0.4309	0.0240	0.5965	0.161*
H11C	0.3425	0.0323	0.4718	0.161*
C12	0.24333 (17)	0.1766 (2)	0.8306 (4)	0.0739 (8)
H12A	0.2284	0.1507	0.9126	0.111*
H12B	0.2239	0.1410	0.7326	0.111*
H12C	0.2212	0.2345	0.8044	0.111*
C13	0.3430 (2)	0.44758 (18)	0.8706 (4)	0.0886 (11)
H13A	0.3249	0.4735	0.9478	0.133*
H13B	0.3111	0.4681	0.7611	0.133*
H13C	0.3969	0.4639	0.8995	0.133*

	U11	U22	U33	U12	U13	U23
O1	0.118 (2)	0.0480 (15)	0.0791 (18)	0.000	0.0745 (17)	0.000
C1	0.074 (2)	0.048 (2)	0.0498 (18)	0.000	0.0438 (17)	0.000
C2	0.0656 (14)	0.0492 (13)	0.0459 (12)	−0.0033 (10)	0.0397 (11)	−0.0017 (10)
O2	0.1371 (18)	0.0460 (11)	0.0952 (15)	−0.0030 (10)	0.0846 (14)	0.0043 (9)
O3	0.0752 (12)	0.0681 (11)	0.0527 (10)	−0.0055 (9)	0.0450 (9)	0.0105 (8)
C3	0.0719 (16)	0.0494 (13)	0.0494 (13)	−0.0013 (11)	0.0422 (12)	0.0001 (10)
O4	0.1063 (14)	0.0569 (11)	0.0782 (12)	−0.0088 (9)	0.0749 (12)	−0.0123 (9)
C4	0.0734 (16)	0.0497 (14)	0.0515 (13)	0.0006 (11)	0.0452 (12)	0.0011 (10)
C5	0.0631 (14)	0.0482 (13)	0.0463 (12)	−0.0029 (10)	0.0384 (11)	−0.0005 (10)
C6	0.0770 (16)	0.0447 (13)	0.0575 (14)	−0.0010 (11)	0.0493 (13)	0.0004 (10)
C7	0.0666 (15)	0.0550 (14)	0.0474 (12)	−0.0045 (11)	0.0414 (12)	−0.0058 (10)
C8	0.0585 (14)	0.0542 (14)	0.0433 (12)	−0.0037 (11)	0.0336 (11)	0.0049 (10)
C9	0.0779 (17)	0.0449 (13)	0.0564 (14)	−0.0038 (11)	0.0443 (13)	0.0040 (11)
C10	0.0807 (17)	0.0506 (14)	0.0556 (14)	0.0013 (12)	0.0487 (13)	−0.0018 (11)
C11	0.188 (4)	0.0482 (18)	0.130 (3)	−0.005 (2)	0.109 (3)	−0.0127 (18)
C12	0.0775 (19)	0.085 (2)	0.0795 (19)	−0.0150 (15)	0.0526 (16)	0.0035 (16)
C13	0.149 (3)	0.0538 (17)	0.108 (2)	−0.0021 (18)	0.098 (2)	−0.0120 (16)

O1—C1	1.222 (4)	C5—C6	1.398 (3)
C1—C2	1.489 (3)	C6—C7	1.389 (3)
C1—C2i	1.489 (3)	C6—H6A	0.9300
C2—C4	1.339 (3)	C7—C8	1.374 (3)
C2—C3	1.501 (3)	C8—C9	1.395 (3)
O2—C9	1.365 (3)	C9—C10	1.386 (3)
O2—C11	1.415 (3)	C10—H10A	0.9300
O3—C8	1.381 (2)	C11—H11A	0.9600
O3—C12	1.420 (3)	C11—H11B	0.9600
C3—C3i	1.541 (4)	C11—H11C	0.9600
C3—H3A	0.9700	C12—H12A	0.9600
C3—H3B	0.9700	C12—H12B	0.9600
O4—C7	1.373 (3)	C12—H12C	0.9600
O4—C13	1.406 (3)	C13—H13A	0.9600
C4—C5	1.462 (3)	C13—H13B	0.9600
C4—H4A	0.9300	C13—H13C	0.9600
C5—C10	1.390 (3)
O1—C1—C2	125.87 (13)	C7—C8—O3	120.62 (19)
O1—C1—C2i	125.87 (13)	C7—C8—C9	119.49 (19)
C2—C1—C2i	108.3 (3)	O3—C8—C9	119.9 (2)
C4—C2—C1	120.7 (2)	O2—C9—C10	124.2 (2)
C4—C2—C3	130.4 (2)	O2—C9—C8	115.7 (2)
C1—C2—C3	108.86 (18)	C10—C9—C8	120.1 (2)
C9—O2—C11	117.7 (2)	C9—C10—C5	120.7 (2)
C8—O3—C12	113.10 (19)	C9—C10—H10A	119.7
C2—C3—C3i	106.72 (11)	C5—C10—H10A	119.7
C2—C3—H3A	110.4	O2—C11—H11A	109.5
C3i—C3—H3A	110.4	O2—C11—H11B	109.5
C2—C3—H3B	110.4	H11A—C11—H11B	109.5
C3i—C3—H3B	110.4	O2—C11—H11C	109.5
H3A—C3—H3B	108.6	H11A—C11—H11C	109.5
C7—O4—C13	117.66 (19)	H11B—C11—H11C	109.5
C2—C4—C5	130.4 (2)	O3—C12—H12A	109.5
C2—C4—H4A	114.8	O3—C12—H12B	109.5
C5—C4—H4A	114.8	H12A—C12—H12B	109.5
C10—C5—C6	118.77 (19)	O3—C12—H12C	109.5
C10—C5—C4	123.87 (19)	H12A—C12—H12C	109.5
C6—C5—C4	117.4 (2)	H12B—C12—H12C	109.5
C7—C6—C5	120.3 (2)	O4—C13—H13A	109.5
C7—C6—H6A	119.9	O4—C13—H13B	109.5
C5—C6—H6A	119.9	H13A—C13—H13B	109.5
O4—C7—C8	115.13 (18)	O4—C13—H13C	109.5
O4—C7—C6	124.2 (2)	H13A—C13—H13C	109.5
C8—C7—C6	120.7 (2)	H13B—C13—H13C	109.5
O1—C1—C2—C4	−2.7 (3)	O4—C7—C8—O3	−2.8 (3)
C2i—C1—C2—C4	177.3 (3)	C6—C7—C8—O3	176.1 (2)
O1—C1—C2—C3	177.49 (12)	O4—C7—C8—C9	178.8 (2)
C2i—C1—C2—C3	−2.51 (12)	C6—C7—C8—C9	−2.2 (4)
C4—C2—C3—C3i	−173.4 (3)	C12—O3—C8—C7	86.9 (3)
C1—C2—C3—C3i	6.4 (3)	C12—O3—C8—C9	−94.7 (3)
C1—C2—C4—C5	178.0 (2)	C11—O2—C9—C10	−5.3 (4)
C3—C2—C4—C5	−2.2 (5)	C11—O2—C9—C8	174.8 (3)
C2—C4—C5—C10	−0.3 (4)	C7—C8—C9—O2	−178.8 (2)
C2—C4—C5—C6	179.6 (3)	O3—C8—C9—O2	2.9 (4)
C10—C5—C6—C7	0.0 (4)	C7—C8—C9—C10	1.3 (4)
C4—C5—C6—C7	−180.0 (2)	O3—C8—C9—C10	−177.0 (2)
C13—O4—C7—C8	−179.2 (3)	O2—C9—C10—C5	−179.7 (2)
C13—O4—C7—C6	1.8 (4)	C8—C9—C10—C5	0.2 (4)
C5—C6—C7—O4	−179.6 (2)	C6—C5—C10—C9	−0.8 (4)
C5—C6—C7—C8	1.6 (4)	C4—C5—C10—C9	179.1 (2)

Table 1

Selected torsion angles (°)

O1—C1—C2—C4	−2.7 (3)
C1—C2—C4—C5	178.0 (2)
C2—C4—C5—C6	179.6 (3)
C13—O4—C7—C6	1.8 (4)
C12—O3—C8—C7	86.9 (3)
C11—O2—C9—C8	174.8 (3)