(2E,6E)-2,6-Bis(4-methyl-benzyl-idene)cyclo-hex-3-en-1-one.

The title compound, C(22)H(20)O, shows an approximately planar cyclo-hexenone ring [maximum deviation = 0.069 (4) Å], with a disordered position of the C=C bond [ratio = 0.71 (2)/0.29 (2)]. The benzene rings of the 4-methyl-benzyl-idene units, attached in the 2- and 6-positions to the cyclo-hexenone ring, are rotated in the same direction by 28.6 (4) and 22.4 (4)°, with respect to the mean plane of the cyclo-hexenone ring [fraction 0.71 (2); maximum deviation = 0.06 (3) Å]. In the crystal, mol-ecules are packed in the manner of a distorted hexa-gonal rod packing with their long axes all aligned along [201]. A number of C-H⋯π inter-actions stablize the crystal structure.

Related literature

For background information to aldol condensation reactions in hetero- and homocyclic ketones, see: Abaee et al. (2007 ▶). For the crystal structure of the analogous compound with 4-meth­oxy­benzyl­idene substituents in the 2- and 6- positions on the cyclo­hexenone ring, see: Abaee et al. (2007 ▶). For other similar substituted cyclo­hexenone structures, see: Shi et al. (2008 ▶); Guo et al. (2008 ▶).

Experimental

Crystal data

C22H20O

M = 300.38

Monoclinic,

a = 10.7108 (14) Å

b = 7.2772 (7) Å

c = 11.4690 (14) Å

β = 114.366 (14)°

V = 814.32 (17) Å3

Z = 2

Mo Kα radiation

μ = 0.07 mm−1

T = 193 K

0.50 × 0.24 × 0.15 mm

Data collection

Stoe IPDS image plate diffractometer

6110 measured reflections

1709 independent reflections

1219 reflections with I > 2σ(I)

R int = 0.060

Refinement

R[F 2 > 2σ(F 2)] = 0.035

wR(F 2) = 0.071

S = 0.98

1709 reflections

212 parameters

3 restraints

H-atom parameters constrained

Δρmax = 0.17 e Å−3

Δρmin = −0.15 e Å−3

Data collection: EXPOSE (Stoe & Cie, 1999 ▶); cell refinement: CELL (Stoe & Cie, 1999 ▶); data reduction: INTEGRATE (Stoe & Cie, 1999 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: DIAMOND (Brandenburg, 2011 ▶); software used to prepare material for publication: publCIF (Westrip 2010 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811055632/su2352sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811055632/su2352Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811055632/su2352Isup3.cml

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

C22H20O	F(000) = 320
Mr = 300.38	Dx = 1.225 Mg m−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 5168 reflections
a = 10.7108 (14) Å	θ = 2.0–25.8°
b = 7.2772 (7) Å	µ = 0.07 mm−1
c = 11.4690 (14) Å	T = 193 K
β = 114.366 (14)°	Block, light-orange
V = 814.32 (17) Å3	0.50 × 0.24 × 0.15 mm
Z = 2

Stoe IPDS image plate diffractometer	1219 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.060
graphite	θmax = 26.0°, θmin = 2.0°
Detector resolution: 6.7 pixels mm-1	h = −13→13
φ–scans	k = −8→8
6110 measured reflections	l = −13→14
1709 independent reflections

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)] = 0.035	Hydrogen site location: difference Fourier map
wR(F2) = 0.071	H-atom parameters constrained
S = 0.98	w = 1/[σ2(Fo2) + (0.030P)2] where P = (Fo2 + 2Fc2)/3
1709 reflections	(Δ/σ)max < 0.001
212 parameters	Δρmax = 0.17 e Å−3
3 restraints	Δρmin = −0.15 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.

	x	y	z	Uiso*/Ueq	Occ. (<1)
O1	1.00222 (16)	0.8042 (5)	0.28700 (15)	0.0927 (11)
C1	0.3618 (2)	0.8455 (4)	−0.22735 (19)	0.0337 (6)
C2	0.3948 (2)	0.7517 (4)	−0.1120 (2)	0.0359 (6)
H2	0.3241	0.6931	−0.0961	0.043*
C3	0.5283 (2)	0.7427 (4)	−0.0206 (2)	0.0336 (6)
H3	0.5473	0.6804	0.0577	0.040*
C4	0.6368 (2)	0.8242 (4)	−0.04127 (19)	0.0310 (5)
C5	0.6034 (2)	0.9148 (4)	−0.1573 (2)	0.0338 (6)
H5	0.6739	0.9705	−0.1749	0.041*
C6	0.4685 (2)	0.9248 (4)	−0.2476 (2)	0.0343 (6)
H6	0.4489	0.9882	−0.3257	0.041*
C7	0.7743 (2)	0.8148 (4)	0.0625 (2)	0.0344 (6)
H7	0.7756	0.7966	0.1449	0.041*
C8	0.8999 (2)	0.8275 (5)	0.0616 (2)	0.0354 (6)
C9	1.0200 (2)	0.8195 (5)	0.1884 (2)	0.0460 (7)
C10	1.1616 (2)	0.8318 (5)	0.19458 (18)	0.0323 (5)
C11	1.1787 (2)	0.8531 (5)	0.07247 (19)	0.0428 (7)
H11A	1.2201	0.9750	0.0734	0.051*	0.71 (2)
H11B	1.2450	0.7592	0.0710	0.051*	0.71 (2)
H11C	1.2680	0.8662	0.0748	0.051*	0.29 (2)
C12A	1.0537 (11)	0.837 (4)	−0.0473 (6)	0.041 (2)	0.71 (2)
H12A	1.0648	0.8253	−0.1250	0.049*	0.71 (2)
C12B	1.0710 (15)	0.854 (12)	−0.0385 (8)	0.041 (2)	0.29 (2)
H12B	1.0869	0.8655	−0.1137	0.049*	0.29 (2)
C13	0.9276 (2)	0.8378 (5)	−0.0544 (2)	0.0445 (6)
H13A	0.8788	0.7335	−0.1099	0.053*	0.29 (2)
H13B	0.8832	0.9514	−0.1004	0.053*	0.29 (2)
H13C	0.8546	0.8343	−0.1373	0.053*	0.71 (2)
C14	1.2658 (2)	0.8164 (4)	0.3111 (2)	0.0351 (6)
H14	1.2366	0.7976	0.3779	0.042*
C15	1.4143 (2)	0.8230 (4)	0.35534 (19)	0.0312 (5)
C16	1.4931 (2)	0.7558 (4)	0.4790 (2)	0.0342 (6)
H16	1.4478	0.7056	0.5276	0.041*
C17	1.6344 (2)	0.7606 (4)	0.5319 (2)	0.0382 (6)
H17	1.6839	0.7136	0.6157	0.046*
C18	1.7060 (2)	0.8332 (5)	0.4649 (2)	0.0372 (6)
C19	1.6289 (2)	0.8998 (4)	0.3425 (2)	0.0371 (7)
H19	1.6750	0.9490	0.2944	0.045*
C20	1.4862 (2)	0.8969 (3)	0.2881 (2)	0.0350 (6)
H20	1.4371	0.9455	0.2046	0.042*
C21	0.2162 (2)	0.8587 (5)	−0.3252 (2)	0.0496 (8)
H21A	0.1559	0.7939	−0.2938	0.074*	0.50
H21B	0.2086	0.8025	−0.4056	0.074*	0.50
H21C	0.1890	0.9881	−0.3401	0.074*	0.50
H21D	0.2131	0.9291	−0.3992	0.074*	0.50
H21E	0.1604	0.9205	−0.2875	0.074*	0.50
H21F	0.1800	0.7349	−0.3529	0.074*	0.50
C22	1.8600 (2)	0.8394 (6)	0.5234 (2)	0.0556 (8)
H22A	1.8959	0.7480	0.5920	0.083*
H22B	1.8909	0.9621	0.5587	0.083*
H22C	1.8935	0.8122	0.4577	0.083*

	U11	U22	U33	U12	U13	U23
O1	0.0368 (9)	0.212 (3)	0.0306 (9)	0.0030 (17)	0.0155 (7)	0.0097 (17)
C1	0.0350 (13)	0.0347 (16)	0.0299 (12)	0.0045 (14)	0.0118 (10)	−0.0026 (14)
C2	0.0321 (13)	0.0397 (16)	0.0388 (14)	−0.0034 (12)	0.0176 (11)	−0.0027 (13)
C3	0.0386 (14)	0.0361 (16)	0.0296 (12)	0.0024 (13)	0.0176 (11)	0.0020 (12)
C4	0.0349 (12)	0.0289 (13)	0.0312 (11)	0.0045 (14)	0.0155 (9)	−0.0022 (15)
C5	0.0343 (13)	0.0342 (15)	0.0364 (13)	−0.0003 (12)	0.0182 (11)	−0.0004 (13)
C6	0.0394 (14)	0.0341 (15)	0.0301 (12)	0.0047 (12)	0.0149 (11)	0.0026 (11)
C7	0.0324 (12)	0.0400 (17)	0.0286 (11)	−0.0001 (13)	0.0105 (9)	−0.0028 (14)
C8	0.0299 (12)	0.0428 (14)	0.0316 (12)	0.0007 (15)	0.0107 (10)	0.0016 (15)
C9	0.0378 (13)	0.070 (2)	0.0324 (12)	0.0009 (16)	0.0169 (11)	−0.0034 (17)
C10	0.0311 (12)	0.0370 (14)	0.0277 (11)	0.0028 (15)	0.0110 (10)	−0.0013 (14)
C11	0.0362 (12)	0.062 (2)	0.0325 (12)	0.0033 (15)	0.0169 (10)	0.0044 (15)
C12A	0.041 (2)	0.054 (7)	0.0294 (12)	−0.002 (5)	0.0169 (14)	0.001 (3)
C12B	0.041 (2)	0.054 (7)	0.0294 (12)	−0.002 (5)	0.0169 (14)	0.001 (3)
C13	0.0358 (13)	0.0627 (18)	0.0334 (12)	0.0018 (16)	0.0126 (10)	−0.0047 (16)
C14	0.0315 (12)	0.0443 (17)	0.0306 (11)	−0.0003 (15)	0.0140 (10)	−0.0024 (15)
C15	0.0354 (12)	0.0321 (14)	0.0252 (11)	−0.0002 (14)	0.0117 (10)	−0.0059 (14)
C16	0.0386 (13)	0.0352 (16)	0.0319 (12)	−0.0023 (12)	0.0175 (11)	−0.0009 (12)
C17	0.0364 (14)	0.0416 (16)	0.0284 (12)	0.0007 (12)	0.0051 (11)	0.0001 (12)
C18	0.0318 (12)	0.0410 (15)	0.0361 (12)	0.0005 (15)	0.0112 (10)	−0.0045 (16)
C19	0.0361 (15)	0.0401 (17)	0.0393 (14)	−0.0032 (12)	0.0197 (12)	−0.0015 (13)
C20	0.0376 (14)	0.0359 (17)	0.0301 (12)	0.0001 (13)	0.0127 (11)	0.0018 (12)
C21	0.0363 (13)	0.066 (2)	0.0384 (13)	0.0014 (15)	0.0075 (11)	0.0007 (16)
C22	0.0354 (14)	0.072 (2)	0.0537 (16)	−0.003 (2)	0.0123 (12)	−0.004 (2)

O1—C9	1.227 (3)	C12B—C13	1.475 (11)
C1—C6	1.383 (3)	C12B—H12B	0.9500
C1—C2	1.398 (3)	C13—H13A	0.9900
C1—C21	1.503 (3)	C13—H13B	0.9900
C2—C3	1.382 (3)	C13—H13C	0.9500
C2—H2	0.9500	C14—C15	1.458 (3)
C3—C4	1.409 (3)	C14—H14	0.9500
C3—H3	0.9500	C15—C20	1.403 (3)
C4—C5	1.393 (3)	C15—C16	1.406 (3)
C4—C7	1.465 (3)	C16—C17	1.379 (3)
C5—C6	1.390 (3)	C16—H16	0.9500
C5—H5	0.9500	C17—C18	1.395 (3)
C6—H6	0.9500	C17—H17	0.9500
C7—C8	1.352 (3)	C18—C19	1.390 (3)
C7—H7	0.9500	C18—C22	1.503 (3)
C8—C13	1.479 (3)	C19—C20	1.392 (3)
C8—C9	1.493 (3)	C19—H19	0.9500
C9—C10	1.491 (3)	C20—H20	0.9500
C10—C14	1.346 (3)	C21—H21A	0.9800
C10—C11	1.494 (3)	C21—H21B	0.9800
C11—C12B	1.319 (12)	C21—H21C	0.9800
C11—C12A	1.475 (9)	C21—H21D	0.9800
C11—H11A	0.9900	C21—H21E	0.9800
C11—H11B	0.9900	C21—H21F	0.9800
C11—H11C	0.9500	C22—H22A	0.9800
C12A—C13	1.319 (10)	C22—H22B	0.9800
C12A—H12A	0.9500	C22—H22C	0.9800
C6—C1—C2	117.35 (19)	C12A—C13—H13B	106.9
C6—C1—C21	121.5 (2)	C12B—C13—H13B	104.3
C2—C1—C21	121.1 (2)	C8—C13—H13B	106.9
C3—C2—C1	121.3 (2)	H13A—C13—H13B	106.7
C3—C2—H2	119.4	C12A—C13—H13C	117.4
C1—C2—H2	119.4	C12B—C13—H13C	120.7
C2—C3—C4	121.3 (2)	C8—C13—H13C	120.7
C2—C3—H3	119.4	H13A—C13—H13C	48.5
C4—C3—H3	119.4	H13B—C13—H13C	58.2
C5—C4—C3	117.09 (19)	C10—C14—C15	133.0 (2)
C5—C4—C7	125.0 (2)	C10—C14—H14	113.5
C3—C4—C7	117.8 (2)	C15—C14—H14	113.5
C6—C5—C4	121.0 (2)	C20—C15—C16	116.78 (19)
C6—C5—H5	119.5	C20—C15—C14	126.1 (2)
C4—C5—H5	119.5	C16—C15—C14	117.1 (2)
C1—C6—C5	122.0 (2)	C17—C16—C15	121.9 (2)
C1—C6—H6	119.0	C17—C16—H16	119.1
C5—C6—H6	119.0	C15—C16—H16	119.1
C8—C7—C4	131.4 (2)	C16—C17—C18	121.4 (2)
C8—C7—H7	114.3	C16—C17—H17	119.3
C4—C7—H7	114.3	C18—C17—H17	119.3
C7—C8—C13	125.34 (19)	C19—C18—C17	117.1 (2)
C7—C8—C9	116.8 (2)	C19—C18—C22	121.8 (2)
C13—C8—C9	117.79 (19)	C17—C18—C22	121.1 (2)
O1—C9—C10	120.20 (19)	C18—C19—C20	122.2 (2)
O1—C9—C8	120.1 (2)	C18—C19—H19	118.9
C10—C9—C8	119.67 (19)	C20—C19—H19	118.9
C14—C10—C9	116.93 (19)	C19—C20—C15	120.6 (2)
C14—C10—C11	124.51 (19)	C19—C20—H20	119.7
C9—C10—C11	118.53 (18)	C15—C20—H20	119.7
C12B—C11—C12A	6(4)	C1—C21—H21A	109.5
C12B—C11—C10	120.5 (4)	C1—C21—H21B	109.5
C12A—C11—C10	116.7 (3)	H21A—C21—H21B	109.5
C12B—C11—H11A	102.5	C1—C21—H21C	109.5
C12A—C11—H11A	108.1	H21A—C21—H21C	109.5
C10—C11—H11A	108.1	H21B—C21—H21C	109.5
C12B—C11—H11B	109.5	C1—C21—H21D	109.5
C12A—C11—H11B	108.1	H21A—C21—H21D	141.1
C10—C11—H11B	108.1	H21B—C21—H21D	56.3
H11A—C11—H11B	107.3	H21C—C21—H21D	56.3
C12B—C11—H11C	119.7	C1—C21—H21E	109.5
C12A—C11—H11C	123.4	H21A—C21—H21E	56.3
C10—C11—H11C	119.7	H21B—C21—H21E	141.1
H11A—C11—H11C	57.9	H21C—C21—H21E	56.3
H11B—C11—H11C	49.5	H21D—C21—H21E	109.5
C13—C12A—C11	124.8 (4)	C1—C21—H21F	109.5
C13—C12A—H12A	117.6	H21A—C21—H21F	56.3
C11—C12A—H12A	117.6	H21B—C21—H21F	56.3
C11—C12B—C13	124.8 (6)	H21C—C21—H21F	141.1
C11—C12B—H12B	117.6	H21D—C21—H21F	109.5
C13—C12B—H12B	117.6	H21E—C21—H21F	109.5
C12A—C13—C12B	6(4)	C18—C22—H22A	109.5
C12A—C13—C8	121.6 (3)	C18—C22—H22B	109.5
C12B—C13—C8	118.5 (3)	H22A—C22—H22B	109.5
C12A—C13—H13A	106.9	C18—C22—H22C	109.5
C12B—C13—H13A	112.7	H22A—C22—H22C	109.5
C8—C13—H13A	106.9	H22B—C22—H22C	109.5
C6—C1—C2—C3	1.5 (4)	C12B—C11—C12A—C13	−121 (34)
C21—C1—C2—C3	−178.6 (3)	C10—C11—C12A—C13	12 (3)
C1—C2—C3—C4	−1.4 (4)	C12A—C11—C12B—C13	50 (25)
C2—C3—C4—C5	0.3 (4)	C10—C11—C12B—C13	1(9)
C2—C3—C4—C7	177.6 (2)	C11—C12A—C13—C12B	50 (25)
C3—C4—C5—C6	0.5 (4)	C11—C12A—C13—C8	−9(3)
C7—C4—C5—C6	−176.5 (2)	C11—C12B—C13—C12A	−121 (34)
C2—C1—C6—C5	−0.7 (4)	C11—C12B—C13—C8	3(9)
C21—C1—C6—C5	179.5 (3)	C7—C8—C13—C12A	−175.2 (17)
C4—C5—C6—C1	−0.4 (4)	C9—C8—C13—C12A	1.1 (17)
C5—C4—C7—C8	−25.5 (5)	C7—C8—C13—C12B	179 (4)
C3—C4—C7—C8	157.5 (3)	C9—C8—C13—C12B	−5(4)
C4—C7—C8—C13	−6.2 (6)	C9—C10—C14—C15	−179.3 (3)
C4—C7—C8—C9	177.4 (3)	C11—C10—C14—C15	3.0 (6)
C7—C8—C9—O1	−0.7 (5)	C10—C14—C15—C20	18.6 (6)
C13—C8—C9—O1	−177.4 (4)	C10—C14—C15—C16	−164.2 (3)
C7—C8—C9—C10	179.7 (3)	C20—C15—C16—C17	−0.5 (4)
C13—C8—C9—C10	3.1 (5)	C14—C15—C16—C17	−178.0 (3)
O1—C9—C10—C14	3.0 (5)	C15—C16—C17—C18	0.1 (4)
C8—C9—C10—C14	−177.4 (3)	C16—C17—C18—C19	−0.2 (4)
O1—C9—C10—C11	−179.1 (4)	C16—C17—C18—C22	179.5 (3)
C8—C9—C10—C11	0.4 (5)	C17—C18—C19—C20	0.6 (4)
C14—C10—C11—C12B	175 (4)	C22—C18—C19—C20	−179.1 (3)
C9—C10—C11—C12B	−3(4)	C18—C19—C20—C15	−1.0 (4)
C14—C10—C11—C12A	170.2 (14)	C16—C15—C20—C19	0.9 (4)
C9—C10—C11—C12A	−7.5 (15)	C14—C15—C20—C19	178.1 (3)

Cg1, Cg2 and Cg3 are the centroids of the C8–C11,C12a,C13, C1–C6 and C15–C20 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···Cg2i	0.95	2.78	3.538 (3)	137
C6—H6···Cg3ii	0.95	2.64	3.423 (3)	139
C16—H16···Cg3iii	0.95	2.85	3.496 (3)	126
C13—H13b···Cg1ii	0.99	2.89	3.642 (6)	134

Table 1

Hydrogen-bond geometry (Å, °)

Cg1, Cg2 and Cg3 are the centroids of the C8–C11,C12a,C13, C1–C6 and C15–C20 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯Cg2i	0.95	2.78	3.538 (3)	137
C6—H6⋯Cg3ii	0.95	2.64	3.423 (3)	139
C16—H16⋯Cg3iii	0.95	2.85	3.496 (3)	126
C13—H13b⋯Cg1ii	0.99	2.89	3.642 (6)	134

Symmetry codes: (i) ; (ii) ; (iii) .