Crystal structure of 5-(4-methyl-phen-yl)-3-[(E)-2-(4-methyl-phen-yl)ethen-yl]cyclo-hex-2-en-1-one.

In the title compound, C22H22O, the dihedral angle between the planes of the benzene rings is 53.55 (7)°. Weak C-H⋯O inter-actions help to direct the packing, forming sheets lying parallel to (020).

Related literature

For the synthesis of cyclo­hexenones and their use as synthons, see: Mayekar et al. (2010 ▸); Suwito et al. (2014 ▸); Tabba et al. (1995 ▸); Bella et al. (2012 ▸); Xing et al. (2010 ▸); Martin & Prasad (2006 ▸). For various biological activities of cyclo­hexenone derivatives, see: Prasad et al. (2006 ▸); Kumar et al. (2003 ▸); Tatsuzaki et al. (2006); Yun et al. (2006 ▸); Kim et al. (2008 ▸); Yoon et al. (2007 ▸); Tanaka et al. (1997 ▸); Vyas et al. (2009 ▸). For the use of cyclo­hexenones as inter­mediates in synthesis, see: Mayekar et al. (2010 ▸); Bella et al. (2012 ▸); Xing et al. (2010); Martin & Prasad (2006 ▸). For the bioactivity of dehydro­zingerone, chalcone and isoeugenol derivatives, see: Tatsuzaki et al. (2006 ▸).

Experimental

Crystal data

C22H22O

M = 302.39

Monoclinic,

a = 4.9614 (1) Å

b = 30.7302 (6) Å

c = 11.0726 (2) Å

β = 93.268 (1)°

V = 1685.44 (6) Å3

Z = 4

Cu Kα radiation

μ = 0.55 mm−1

T = 150 K

0.31 × 0.11 × 0.08 mm

Data collection

Bruker D8 VENTURE PHOTON 100 CMOS diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2014 ▸) T min = 0.84, T max = 0.96

12558 measured reflections

3247 independent reflections

2529 reflections with I > 2σ(I)

R int = 0.042

Refinement

R[F 2 > 2σ(F 2)] = 0.050

wR(F 2) = 0.131

S = 1.05

3247 reflections

210 parameters

H-atom parameters constrained

Δρmax = 0.35 e Å−3

Δρmin = −0.19 e Å−3

Data collection: APEX2 (Bruker, 2014 ▸); cell refinement: SAINT (Bruker, 2014 ▸); data reduction: SAINT; program(s) used to solve structure: SHELXT (Sheldrick, 2015a ▸); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b ▸); molecular graphics: DIAMOND (Brandenburg & Putz, 2012 ▸); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▸).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S2056989015008324/lr2135sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015008324/lr2135Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S2056989015008324/lr2135Isup3.cml

Click here for additional data file.

. DOI: 10.1107/S2056989015008324/lr2135fig1.tif

The title mol­ecule with labeling scheme and 50% probability ellipsoids.

Click here for additional data file.

. DOI: 10.1107/S2056989015008324/lr2135fig2.tif

Packing viewed towards the (10)plane. Weak C—H⋯O inter­actions are shown as dotted lines.

CCDC reference: 1062089

Additional supporting information: crystallographic information; 3D view; checkCIF report

C22H22O	F(000) = 648
Mr = 302.39	Dx = 1.192 Mg m−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.54178 Å
a = 4.9614 (1) Å	Cell parameters from 7504 reflections
b = 30.7302 (6) Å	θ = 2.9–72.6°
c = 11.0726 (2) Å	µ = 0.55 mm−1
β = 93.268 (1)°	T = 150 K
V = 1685.44 (6) Å3	Column, colourless
Z = 4	0.31 × 0.11 × 0.08 mm

Bruker D8 VENTURE PHOTON 100 CMOS diffractometer	3247 independent reflections
Radiation source: INCOATEC IµS micro-focus source	2529 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.042
Detector resolution: 10.4167 pixels mm-1	θmax = 72.4°, θmin = 4.3°
ω scans	h = −5→6
Absorption correction: multi-scan (SADABS; Bruker, 2014)	k = −38→36
Tmin = 0.84, Tmax = 0.96	l = −11→13
12558 measured 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)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.131	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0579P)2 + 0.6292P] where P = (Fo2 + 2Fc2)/3
3247 reflections	(Δ/σ)max = 0.001
210 parameters	Δρmax = 0.35 e Å−3
0 restraints	Δρmin = −0.19 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 takeninto account individually in the estimation of e.s.d.'s in distances, anglesand torsion angles; correlations between e.s.d.'s in cell parameters are onlyused 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. H-atoms were placed in calculated positions (C—H = 0.95 - 0.98 Å) and included as riding contributions with isotropic displacement parameters 1.2 - 1.5 times those of the attached carbon atoms.

	x	y	z	Uiso*/Ueq
O1	−0.2370 (3)	0.78680 (4)	0.50574 (12)	0.0422 (3)
C1	−0.0733 (4)	0.77848 (6)	0.42988 (16)	0.0324 (4)
C2	−0.0376 (4)	0.73445 (6)	0.38590 (16)	0.0320 (4)
H2	−0.1435	0.7119	0.4177	0.038*
C3	0.1391 (3)	0.72401 (5)	0.30189 (15)	0.0280 (4)
C4	0.2939 (4)	0.75888 (5)	0.23953 (15)	0.0298 (4)
H4A	0.2923	0.7521	0.1521	0.036*
H4B	0.4841	0.7583	0.2718	0.036*
C5	0.1810 (4)	0.80493 (6)	0.25518 (16)	0.0331 (4)
H5	0.0083	0.8068	0.2043	0.040*
C6	0.1127 (4)	0.81281 (6)	0.38459 (17)	0.0369 (4)
H6A	0.2814	0.8132	0.4368	0.044*
H6B	0.0257	0.8417	0.3905	0.044*
C7	0.1933 (4)	0.67865 (6)	0.27681 (16)	0.0313 (4)
H7	0.0800	0.6575	0.3107	0.038*
C8	0.3907 (4)	0.66425 (5)	0.20954 (15)	0.0295 (4)
H8	0.4884	0.6858	0.1686	0.035*
C9	0.4725 (3)	0.61914 (6)	0.19209 (15)	0.0296 (4)
C10	0.3664 (4)	0.58378 (6)	0.25307 (18)	0.0389 (4)
H10	0.2265	0.5885	0.3067	0.047*
C11	0.4619 (4)	0.54214 (6)	0.23644 (18)	0.0392 (4)
H11	0.3877	0.5188	0.2800	0.047*
C12	0.6632 (4)	0.53343 (6)	0.15784 (17)	0.0355 (4)
C13	0.7678 (4)	0.56848 (6)	0.09696 (17)	0.0394 (5)
H13	0.9057	0.5635	0.0424	0.047*
C14	0.6762 (4)	0.61052 (6)	0.11375 (16)	0.0341 (4)
H14	0.7534	0.6338	0.0712	0.041*
C15	0.7656 (5)	0.48793 (6)	0.1393 (2)	0.0466 (5)
H15A	0.7277	0.4700	0.2095	0.070*
H15B	0.9608	0.4888	0.1300	0.070*
H15C	0.6750	0.4754	0.0664	0.070*
C16	0.3727 (4)	0.83857 (5)	0.20647 (15)	0.0310 (4)
C17	0.4337 (4)	0.83682 (6)	0.08492 (16)	0.0348 (4)
H17	0.3555	0.8146	0.0345	0.042*
C18	0.6061 (4)	0.86683 (6)	0.03656 (16)	0.0357 (4)
H18	0.6431	0.8648	−0.0465	0.043*
C19	0.7260 (4)	0.89973 (6)	0.10667 (17)	0.0339 (4)
C20	0.6674 (4)	0.90135 (6)	0.22736 (18)	0.0394 (4)
H20	0.7471	0.9234	0.2777	0.047*
C21	0.4943 (4)	0.87140 (6)	0.27656 (17)	0.0378 (4)
H21	0.4585	0.8734	0.3597	0.045*
C22	0.9152 (4)	0.93214 (7)	0.0529 (2)	0.0450 (5)
H22A	1.1003	0.9209	0.0606	0.068*
H22B	0.9060	0.9599	0.0960	0.068*
H22C	0.8619	0.9366	−0.0328	0.068*

	U11	U22	U33	U12	U13	U23
O1	0.0419 (8)	0.0429 (7)	0.0440 (8)	0.0040 (6)	0.0210 (6)	−0.0051 (6)
C1	0.0284 (9)	0.0378 (10)	0.0315 (9)	0.0061 (7)	0.0061 (7)	0.0004 (7)
C2	0.0292 (9)	0.0332 (9)	0.0344 (9)	0.0010 (7)	0.0078 (7)	0.0028 (7)
C3	0.0261 (8)	0.0302 (9)	0.0277 (9)	0.0019 (7)	0.0017 (6)	0.0011 (6)
C4	0.0315 (9)	0.0296 (9)	0.0287 (9)	0.0011 (7)	0.0067 (7)	−0.0015 (6)
C5	0.0362 (9)	0.0314 (9)	0.0323 (9)	0.0015 (7)	0.0074 (7)	−0.0021 (7)
C6	0.0390 (10)	0.0312 (9)	0.0417 (10)	0.0040 (8)	0.0116 (8)	−0.0033 (7)
C7	0.0325 (9)	0.0292 (9)	0.0329 (9)	−0.0021 (7)	0.0076 (7)	0.0017 (7)
C8	0.0340 (9)	0.0285 (8)	0.0263 (8)	−0.0009 (7)	0.0051 (7)	0.0002 (6)
C9	0.0326 (9)	0.0289 (9)	0.0276 (9)	−0.0004 (7)	0.0038 (7)	−0.0006 (6)
C10	0.0439 (11)	0.0328 (9)	0.0417 (10)	−0.0010 (8)	0.0176 (8)	−0.0004 (8)
C11	0.0471 (11)	0.0299 (9)	0.0415 (11)	−0.0027 (8)	0.0109 (8)	0.0032 (7)
C12	0.0420 (10)	0.0287 (9)	0.0354 (10)	0.0038 (8)	−0.0006 (8)	−0.0027 (7)
C13	0.0438 (11)	0.0358 (10)	0.0401 (10)	0.0053 (8)	0.0150 (8)	−0.0029 (8)
C14	0.0402 (10)	0.0306 (9)	0.0326 (9)	−0.0001 (7)	0.0115 (8)	0.0010 (7)
C15	0.0545 (13)	0.0334 (10)	0.0522 (13)	0.0081 (9)	0.0064 (10)	−0.0006 (9)
C16	0.0358 (9)	0.0267 (8)	0.0309 (9)	0.0027 (7)	0.0069 (7)	−0.0011 (7)
C17	0.0418 (10)	0.0309 (9)	0.0321 (9)	−0.0019 (8)	0.0058 (7)	−0.0044 (7)
C18	0.0418 (10)	0.0350 (10)	0.0312 (9)	0.0033 (8)	0.0102 (8)	0.0012 (7)
C19	0.0322 (9)	0.0305 (9)	0.0396 (10)	0.0032 (7)	0.0077 (7)	0.0023 (7)
C20	0.0435 (11)	0.0352 (10)	0.0399 (11)	−0.0067 (8)	0.0064 (8)	−0.0068 (8)
C21	0.0468 (11)	0.0361 (10)	0.0315 (10)	−0.0041 (8)	0.0099 (8)	−0.0056 (7)
C22	0.0444 (12)	0.0414 (11)	0.0506 (12)	−0.0057 (9)	0.0143 (9)	0.0013 (9)

O1—C1	1.228 (2)	C11—H11	0.9500
C1—C2	1.452 (2)	C12—C13	1.387 (3)
C1—C6	1.506 (3)	C12—C15	1.506 (2)
C2—C3	1.352 (2)	C13—C14	1.386 (2)
C2—H2	0.9500	C13—H13	0.9500
C3—C7	1.450 (2)	C14—H14	0.9500
C3—C4	1.508 (2)	C15—H15A	0.9800
C4—C5	1.535 (2)	C15—H15B	0.9800
C4—H4A	0.9900	C15—H15C	0.9800
C4—H4B	0.9900	C16—C21	1.390 (3)
C5—C6	1.511 (2)	C16—C17	1.397 (2)
C5—C16	1.524 (2)	C17—C18	1.386 (3)
C5—H5	1.0000	C17—H17	0.9500
C6—H6A	0.9900	C18—C19	1.388 (3)
C6—H6B	0.9900	C18—H18	0.9500
C7—C8	1.339 (2)	C19—C20	1.385 (3)
C7—H7	0.9500	C19—C22	1.514 (3)
C8—C9	1.460 (2)	C20—C21	1.391 (3)
C8—H8	0.9500	C20—H20	0.9500
C9—C14	1.394 (2)	C21—H21	0.9500
C9—C10	1.398 (2)	C22—H22A	0.9800
C10—C11	1.381 (3)	C22—H22B	0.9800
C10—H10	0.9500	C22—H22C	0.9800
C11—C12	1.388 (3)
O1—C1—C2	121.44 (16)	C12—C11—H11	119.1
O1—C1—C6	121.55 (16)	C13—C12—C11	117.25 (16)
C2—C1—C6	116.89 (15)	C13—C12—C15	121.09 (17)
C3—C2—C1	123.22 (16)	C11—C12—C15	121.66 (17)
C3—C2—H2	118.4	C14—C13—C12	121.60 (17)
C1—C2—H2	118.4	C14—C13—H13	119.2
C2—C3—C7	119.64 (15)	C12—C13—H13	119.2
C2—C3—C4	120.88 (15)	C13—C14—C9	121.04 (16)
C7—C3—C4	119.37 (14)	C13—C14—H14	119.5
C3—C4—C5	113.86 (14)	C9—C14—H14	119.5
C3—C4—H4A	108.8	C12—C15—H15A	109.5
C5—C4—H4A	108.8	C12—C15—H15B	109.5
C3—C4—H4B	108.8	H15A—C15—H15B	109.5
C5—C4—H4B	108.8	C12—C15—H15C	109.5
H4A—C4—H4B	107.7	H15A—C15—H15C	109.5
C6—C5—C16	113.91 (15)	H15B—C15—H15C	109.5
C6—C5—C4	110.97 (14)	C21—C16—C17	117.07 (16)
C16—C5—C4	110.25 (14)	C21—C16—C5	123.69 (16)
C6—C5—H5	107.1	C17—C16—C5	119.24 (16)
C16—C5—H5	107.1	C18—C17—C16	121.24 (17)
C4—C5—H5	107.1	C18—C17—H17	119.4
C1—C6—C5	112.23 (15)	C16—C17—H17	119.4
C1—C6—H6A	109.2	C17—C18—C19	121.53 (17)
C5—C6—H6A	109.2	C17—C18—H18	119.2
C1—C6—H6B	109.2	C19—C18—H18	119.2
C5—C6—H6B	109.2	C20—C19—C18	117.33 (17)
H6A—C6—H6B	107.9	C20—C19—C22	121.69 (17)
C8—C7—C3	125.02 (16)	C18—C19—C22	120.98 (17)
C8—C7—H7	117.5	C19—C20—C21	121.51 (17)
C3—C7—H7	117.5	C19—C20—H20	119.2
C7—C8—C9	127.22 (16)	C21—C20—H20	119.2
C7—C8—H8	116.4	C16—C21—C20	121.32 (17)
C9—C8—H8	116.4	C16—C21—H21	119.3
C14—C9—C10	117.34 (16)	C20—C21—H21	119.3
C14—C9—C8	118.65 (15)	C19—C22—H22A	109.5
C10—C9—C8	123.97 (16)	C19—C22—H22B	109.5
C11—C10—C9	120.96 (17)	H22A—C22—H22B	109.5
C11—C10—H10	119.5	C19—C22—H22C	109.5
C9—C10—H10	119.5	H22A—C22—H22C	109.5
C10—C11—C12	121.80 (17)	H22B—C22—H22C	109.5
C10—C11—H11	119.1
O1—C1—C2—C3	179.54 (18)	C10—C11—C12—C15	−179.6 (2)
C6—C1—C2—C3	−4.5 (3)	C11—C12—C13—C14	0.1 (3)
C1—C2—C3—C7	170.34 (16)	C15—C12—C13—C14	−179.66 (19)
C1—C2—C3—C4	−5.8 (3)	C12—C13—C14—C9	−0.6 (3)
C2—C3—C4—C5	−14.9 (2)	C10—C9—C14—C13	0.3 (3)
C7—C3—C4—C5	169.05 (15)	C8—C9—C14—C13	177.83 (17)
C3—C4—C5—C6	44.1 (2)	C6—C5—C16—C21	5.5 (3)
C3—C4—C5—C16	171.31 (15)	C4—C5—C16—C21	−120.04 (19)
O1—C1—C6—C5	−149.12 (18)	C6—C5—C16—C17	−174.85 (17)
C2—C1—C6—C5	34.9 (2)	C4—C5—C16—C17	59.6 (2)
C16—C5—C6—C1	−179.03 (15)	C21—C16—C17—C18	−0.6 (3)
C4—C5—C6—C1	−53.9 (2)	C5—C16—C17—C18	179.74 (17)
C2—C3—C7—C8	−169.72 (18)	C16—C17—C18—C19	0.2 (3)
C4—C3—C7—C8	6.4 (3)	C17—C18—C19—C20	0.2 (3)
C3—C7—C8—C9	172.86 (17)	C17—C18—C19—C22	179.64 (18)
C7—C8—C9—C14	177.15 (18)	C18—C19—C20—C21	−0.3 (3)
C7—C8—C9—C10	−5.5 (3)	C22—C19—C20—C21	−179.72 (19)
C14—C9—C10—C11	0.4 (3)	C17—C16—C21—C20	0.5 (3)
C8—C9—C10—C11	−176.95 (18)	C5—C16—C21—C20	−179.83 (18)
C9—C10—C11—C12	−0.9 (3)	C19—C20—C21—C16	0.0 (3)
C10—C11—C12—C13	0.6 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6A···O1i	0.99	2.60	3.515 (2)	154
C8—H8···O1ii	0.95	2.47	3.353 (2)	155
C14—H14···O1ii	0.95	2.55	3.410 (2)	151

Table 1

Hydrogen-bond geometry (, )

DHA	DH	HA	D A	DHA
C6H6AO1i	0.99	2.60	3.515(2)	154
C8H8O1ii	0.95	2.47	3.353(2)	155
C14H14O1ii	0.95	2.55	3.410(2)	151

Symmetry codes: (i) ; (ii) .