(2E,6E)-2,6-Bis(4-ethoxy-benzyl-idene)cyclo-hexa-none.

The title compound, C(24)H(26)O(3), was prepared by the condensation reaction of 4-ethoxy-benzaldehyde with cyclo-hexa-none. The mol-ecule has crystallographic mirror symmetry and exhibits a butterfly-shaped geometry, with a dihedral angle of 5.46 (1)° between the two benzene rings. Weak inter-molecular C-H⋯π inter-actions help stabilize the crystal structure.

Related literature

For related structures, see: Du et al. (2007 ▶); Liang et al. (2007 ▶); Sun et al. (2007 ▶); Zhou et al. (2007 ▶). For background information, see: Guilford et al. (1999 ▶); Ompraba et al. (2003 ▶); Yu et al. (2000 ▶).

Experimental

Crystal data

C24H26O3

M = 362.45

Orthorhombic,

a = 24.2516 (6) Å

b = 10.8459 (3) Å

c = 7.5270 (2) Å

V = 1979.83 (9) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 298 (2) K

0.20 × 0.10 × 0.10 mm

Data collection

Bruker SMART 4K CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1997 ▶) T min = 0.974, T max = 0.992

6002 measured reflections

1026 independent reflections

879 reflections with I > 2σ(I)

R int = 0.121

Refinement

R[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.115

S = 1.05

1026 reflections

129 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.20 e Å−3

Δρmin = −0.14 e Å−3

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 1999 ▶); data reduction: SAINT; 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 I, global. DOI: 10.1107/S1600536808034272/bg2205sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808034272/bg2205Isup2.hkl

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

C24H26O3	F(000) = 776
Mr = 362.45	Dx = 1.216 Mg m−3
Orthorhombic, Cmc21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C2c-2	Cell parameters from 1880 reflections
a = 24.2516 (6) Å	θ = 2.7–21.4°
b = 10.8459 (3) Å	µ = 0.08 mm−1
c = 7.5270 (2) Å	T = 298 K
V = 1979.83 (9) Å3	Block, colourless
Z = 4	0.20 × 0.10 × 0.10 mm

Bruker SMART 4K CCD area-detector diffractometer	1026 independent reflections
Radiation source: fine-focus sealed tube	879 reflections with I > 2σ(I)
graphite	Rint = 0.121
φ and ω scans	θmax = 25.5°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1997)	h = −24→29
Tmin = 0.974, Tmax = 0.992	k = −12→13
6002 measured reflections	l = −9→9

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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.115	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0642P)2] where P = (Fo2 + 2Fc2)/3
1026 reflections	(Δ/σ)max < 0.001
129 parameters	Δρmax = 0.20 e Å−3
1 restraint	Δρmin = −0.14 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. The authors have merged Friedel pairs before the final refinement. In the absence of anomalous scatterers, no attempt was made to establish the absolute configuration of the title compound.

	x	y	z	Uiso*/Ueq
C1	0.5000	0.2069 (4)	0.1013 (7)	0.0752 (13)
C2	0.44694 (11)	0.1650 (2)	0.1831 (4)	0.0599 (7)
C3	0.44890 (11)	0.0930 (3)	0.3532 (4)	0.0641 (8)
H3A	0.4486	0.0056	0.3262	0.077*
H3B	0.4163	0.1114	0.4231	0.077*
C4	0.5000	0.1232 (4)	0.4615 (5)	0.0713 (11)
H4A	0.5000	0.2100	0.4926	0.086*
H4B	0.5000	0.0755	0.5705	0.086*
C5	0.40084 (12)	0.1962 (2)	0.0943 (4)	0.0604 (8)
H5	0.4067	0.2472	−0.0033	0.072*
C6	0.34301 (12)	0.1637 (2)	0.1252 (3)	0.0534 (7)
C7	0.32483 (12)	0.0581 (2)	0.2149 (4)	0.0568 (8)
H7	0.3507	0.0059	0.2663	0.068*
C8	0.26987 (12)	0.0298 (2)	0.2288 (3)	0.0561 (7)
H8	0.2590	−0.0412	0.2885	0.067*
C9	0.23052 (12)	0.1066 (2)	0.1543 (4)	0.0535 (7)
C10	0.24723 (12)	0.2127 (2)	0.0674 (4)	0.0585 (7)
H10	0.2212	0.2658	0.0188	0.070*
C11	0.30222 (11)	0.2389 (2)	0.0536 (4)	0.0572 (7)
H11	0.3128	0.3101	−0.0062	0.069*
C12	0.13522 (12)	0.1324 (3)	0.0784 (6)	0.0798 (10)
H12A	0.1433	0.1310	−0.0477	0.096*
H12B	0.1331	0.2177	0.1168	0.096*
C13	0.08165 (14)	0.0681 (4)	0.1142 (7)	0.1005 (14)
H13A	0.0865	−0.0193	0.1008	0.151*
H13B	0.0543	0.0965	0.0316	0.151*
H13C	0.0698	0.0858	0.2332	0.151*
O1	0.5000	0.2707 (5)	−0.0304 (6)	0.1303 (19)
O2	0.17725 (8)	0.06933 (16)	0.1745 (3)	0.0673 (6)

	U11	U22	U33	U12	U13	U23
C1	0.074 (3)	0.070 (2)	0.082 (3)	0.000	0.000	0.028 (2)
C2	0.0684 (18)	0.0474 (13)	0.0640 (18)	0.0046 (12)	0.0043 (15)	0.0077 (13)
C3	0.0661 (18)	0.0647 (19)	0.0614 (17)	0.0063 (13)	0.0094 (15)	0.0044 (15)
C4	0.085 (3)	0.077 (3)	0.052 (2)	0.000	0.000	0.000 (2)
C5	0.073 (2)	0.0483 (14)	0.0598 (17)	0.0014 (11)	0.0048 (14)	0.0111 (12)
C6	0.0702 (17)	0.0420 (13)	0.0481 (14)	0.0040 (11)	−0.0010 (13)	0.0023 (11)
C7	0.071 (2)	0.0422 (13)	0.0567 (17)	0.0091 (12)	0.0011 (14)	0.0086 (12)
C8	0.0723 (18)	0.0427 (14)	0.0532 (15)	0.0006 (12)	0.0008 (14)	0.0082 (12)
C9	0.0663 (17)	0.0460 (14)	0.0482 (14)	−0.0013 (11)	0.0004 (13)	−0.0063 (12)
C10	0.0701 (19)	0.0449 (14)	0.0605 (16)	0.0083 (12)	−0.0071 (14)	0.0016 (13)
C11	0.0731 (17)	0.0403 (14)	0.0583 (15)	−0.0021 (11)	−0.0034 (15)	0.0083 (11)
C12	0.072 (2)	0.075 (2)	0.092 (3)	0.0082 (16)	−0.008 (2)	0.0095 (19)
C13	0.065 (2)	0.099 (2)	0.138 (4)	0.0051 (17)	−0.004 (2)	0.008 (3)
O1	0.076 (2)	0.170 (4)	0.145 (4)	0.000	0.000	0.110 (4)
O2	0.0661 (13)	0.0624 (10)	0.0733 (14)	−0.0012 (9)	−0.0051 (12)	0.0077 (11)

C1—O1	1.209 (6)	C7—H7	0.9300
C1—C2i	1.497 (4)	C8—C9	1.385 (4)
C1—C2	1.497 (4)	C8—H8	0.9300
C2—C5	1.346 (4)	C9—O2	1.362 (3)
C2—C3	1.500 (4)	C9—C10	1.384 (4)
C3—C4	1.519 (4)	C10—C11	1.367 (4)
C3—H3A	0.9700	C10—H10	0.9300
C3—H3B	0.9700	C11—H11	0.9300
C4—C3i	1.519 (4)	C12—O2	1.425 (4)
C4—H4A	0.9700	C12—C13	1.499 (5)
C4—H4B	0.9700	C12—H12A	0.9700
C5—C6	1.465 (4)	C12—H12B	0.9700
C5—H5	0.9300	C13—H13A	0.9600
C6—C11	1.391 (4)	C13—H13B	0.9600
C6—C7	1.400 (4)	C13—H13C	0.9600
C7—C8	1.372 (4)
O1—C1—C2i	120.73 (18)	C6—C7—H7	119.1
O1—C1—C2	120.73 (18)	C7—C8—C9	120.3 (2)
C2i—C1—C2	118.5 (4)	C7—C8—H8	119.9
C5—C2—C1	115.7 (3)	C9—C8—H8	119.9
C5—C2—C3	125.5 (3)	O2—C9—C10	125.3 (2)
C1—C2—C3	118.8 (3)	O2—C9—C8	115.4 (2)
C2—C3—C4	111.8 (3)	C10—C9—C8	119.3 (3)
C2—C3—H3A	109.3	C11—C10—C9	119.6 (3)
C4—C3—H3A	109.3	C11—C10—H10	120.2
C2—C3—H3B	109.3	C9—C10—H10	120.2
C4—C3—H3B	109.3	C10—C11—C6	122.8 (3)
H3A—C3—H3B	107.9	C10—C11—H11	118.6
C3i—C4—C3	109.3 (3)	C6—C11—H11	118.6
C3i—C4—H4A	109.8	O2—C12—C13	107.8 (3)
C3—C4—H4A	109.8	O2—C12—H12A	110.2
C3i—C4—H4B	109.8	C13—C12—H12A	110.2
C3—C4—H4B	109.8	O2—C12—H12B	110.2
H4A—C4—H4B	108.3	C13—C12—H12B	110.2
C2—C5—C6	131.0 (3)	H12A—C12—H12B	108.5
C2—C5—H5	114.5	C12—C13—H13A	109.5
C6—C5—H5	114.5	C12—C13—H13B	109.5
C11—C6—C7	116.3 (3)	H13A—C13—H13B	109.5
C11—C6—C5	118.6 (2)	C12—C13—H13C	109.5
C7—C6—C5	125.1 (3)	H13A—C13—H13C	109.5
C8—C7—C6	121.7 (2)	H13B—C13—H13C	109.5
C8—C7—H7	119.1	C9—O2—C12	118.6 (2)
O1—C1—C2—C5	4.1 (7)	C5—C6—C7—C8	−175.8 (3)
C2i—C1—C2—C5	−174.1 (3)	C6—C7—C8—C9	−0.4 (4)
O1—C1—C2—C3	−176.0 (5)	C7—C8—C9—O2	179.5 (3)
C2i—C1—C2—C3	5.7 (6)	C7—C8—C9—C10	−0.7 (4)
C5—C2—C3—C4	−153.2 (3)	O2—C9—C10—C11	−179.0 (3)
C1—C2—C3—C4	27.0 (4)	C8—C9—C10—C11	1.2 (4)
C2—C3—C4—C3i	−59.6 (4)	C9—C10—C11—C6	−0.7 (5)
C1—C2—C5—C6	174.4 (3)	C7—C6—C11—C10	−0.4 (4)
C3—C2—C5—C6	−5.4 (5)	C5—C6—C11—C10	176.5 (3)
C2—C5—C6—C11	158.6 (3)	C10—C9—O2—C12	9.9 (4)
C2—C5—C6—C7	−24.8 (5)	C8—C9—O2—C12	−170.3 (3)
C11—C6—C7—C8	1.0 (4)	C13—C12—O2—C9	176.1 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8···Cg1ii	0.93	2.92	3.601 (2)	132

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C8—H8⋯Cg1i	0.93	2.92	3.601 (2)	132

Symmetry code: (i) . Cg1 is the centroid of atoms C6–C11.