5-(4-Methyl-phen-yl)-3-phenyl-cyclo-hex-2-en-1-one.

In the title compound, C(19)H(18)O, the cyclo-hexene ring has an envelope conformation with the methine C atom on the flap. The phenyl and methyl-phenyl rings form a dihedral angle of 85.93 (11)°. The crystal packing is consolidated by van der Waals forces and weak C-H⋯π inter-actions.

Related literature

For the biological activity of α,β-unsaturated carbonyl compounds, see: Podraze (1991 ▶); Suksamrarn et al. (2003 ▶); Modzelewska et al. (2006 ▶); Shettigar et al. (2006 ▶); Ferrer et al. (2009 ▶); Asiri (2003 ▶); Forestier et al. (1989 ▶); Kumar et al. (2003 ▶). For the synthesis of cyclo­hexenones, see: Diao & Stahl (2011 ▶); González et al. (2009 ▶); Zhang et al. (2008 ▶). For geometric analysis, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

C19H18O

M = 262.33

Monoclinic,

a = 17.085 (4) Å

b = 5.6807 (11) Å

c = 15.689 (3) Å

β = 113.152 (4)°

V = 1400.1 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 150 K

0.42 × 0.24 × 0.12 mm

Data collection

Bruker APEX 2000 CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.979, T max = 0.991

9636 measured reflections

2473 independent reflections

1497 reflections with I > 2σ(I)

R int = 0.106

Refinement

R[F 2 > 2σ(F 2)] = 0.053

wR(F 2) = 0.114

S = 0.90

2473 reflections

182 parameters

H-atom parameters constrained

Δρmax = 0.22 e Å−3

Δρmin = −0.19 e Å−3

Data collection: SMART (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812027031/xu5565sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812027031/xu5565Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812027031/xu5565Isup3.cml

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

C19H18O	F(000) = 560
Mr = 262.33	Dx = 1.245 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 879 reflections
a = 17.085 (4) Å	θ = 2.6–28.4°
b = 5.6807 (11) Å	µ = 0.08 mm−1
c = 15.689 (3) Å	T = 150 K
β = 113.152 (4)°	Plate, colourless
V = 1400.1 (5) Å3	0.42 × 0.24 × 0.12 mm
Z = 4

Bruker APEX 2000 CCD area-detector diffractometer	2473 independent reflections
Radiation source: fine-focus sealed tube	1497 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.106
phi and ω scans	θmax = 25.0°, θmin = 2.6°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −20→20
Tmin = 0.979, Tmax = 0.991	k = −6→6
9636 measured reflections	l = −18→18

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)] = 0.053	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.114	H-atom parameters constrained
S = 0.90	w = 1/[σ2(Fo2) + (0.040P)2] where P = (Fo2 + 2Fc2)/3
2473 reflections	(Δ/σ)max < 0.001
182 parameters	Δρmax = 0.22 e Å−3
0 restraints	Δρmin = −0.19 e Å−3

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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	0.26608 (10)	0.8925 (3)	1.12374 (11)	0.0414 (6)
C1	0.23739 (15)	0.7390 (4)	1.06451 (16)	0.0310 (8)
C2	0.14596 (15)	0.7212 (4)	1.00905 (15)	0.0297 (8)
C3	0.11153 (14)	0.5617 (4)	0.94080 (15)	0.0240 (8)
C4	0.16904 (13)	0.3960 (4)	0.91730 (15)	0.0279 (8)
C5	0.25840 (14)	0.4974 (4)	0.94353 (15)	0.0278 (8)
C6	0.29405 (14)	0.5614 (4)	1.04625 (15)	0.0329 (8)
C7	0.01837 (14)	0.5429 (4)	0.88700 (15)	0.0253 (8)
C8	−0.01655 (14)	0.3458 (4)	0.83212 (15)	0.0303 (8)
C9	−0.10293 (15)	0.3268 (4)	0.78170 (16)	0.0337 (9)
C10	−0.15772 (14)	0.5021 (4)	0.78364 (16)	0.0312 (8)
C11	−0.12489 (15)	0.6993 (4)	0.83717 (16)	0.0315 (9)
C12	−0.03831 (14)	0.7195 (4)	0.88790 (15)	0.0299 (8)
C13	0.31421 (13)	0.3378 (4)	0.91407 (15)	0.0258 (8)
C14	0.34825 (14)	0.1297 (4)	0.96021 (16)	0.0297 (8)
C15	0.39595 (14)	−0.0172 (4)	0.92875 (16)	0.0326 (8)
C16	0.41086 (14)	0.0364 (4)	0.85029 (16)	0.0298 (8)
C17	0.37680 (14)	0.2433 (4)	0.80440 (17)	0.0315 (8)
C18	0.32954 (14)	0.3917 (4)	0.83590 (16)	0.0299 (8)
C19	0.46239 (15)	−0.1244 (5)	0.81565 (18)	0.0438 (10)
H2	0.10900	0.82740	1.02180	0.0360*
H4A	0.14380	0.36270	0.84990	0.0330*
H4B	0.17310	0.24530	0.95050	0.0330*
H5	0.25190	0.64790	0.90840	0.0330*
H6A	0.29790	0.41820	1.08370	0.0390*
H6B	0.35200	0.62730	1.06470	0.0390*
H8	0.01990	0.22230	0.82950	0.0360*
H9	−0.12500	0.19050	0.74500	0.0400*
H10	−0.21720	0.48770	0.74870	0.0370*
H11	−0.16200	0.82180	0.83910	0.0380*
H12	−0.01680	0.85660	0.92430	0.0360*
H14	0.33870	0.08750	1.01390	0.0360*
H15	0.41900	−0.15800	0.96180	0.0390*
H17	0.38590	0.28460	0.75030	0.0380*
H18	0.30720	0.53340	0.80320	0.0360*
H19A	0.42480	−0.19810	0.75740	0.0660*
H19B	0.48940	−0.24660	0.86200	0.0660*
H19C	0.50630	−0.03270	0.80500	0.0660*

	U11	U22	U33	U12	U13	U23
O1	0.0401 (11)	0.0482 (12)	0.0358 (10)	−0.0067 (9)	0.0149 (9)	−0.0171 (9)
C1	0.0361 (15)	0.0347 (15)	0.0259 (14)	−0.0045 (12)	0.0162 (12)	−0.0028 (12)
C2	0.0302 (14)	0.0327 (15)	0.0303 (14)	0.0009 (11)	0.0162 (12)	−0.0025 (12)
C3	0.0284 (14)	0.0235 (14)	0.0236 (12)	0.0014 (11)	0.0139 (11)	0.0030 (11)
C4	0.0288 (14)	0.0281 (14)	0.0275 (13)	0.0007 (11)	0.0119 (11)	−0.0002 (11)
C5	0.0288 (13)	0.0285 (14)	0.0260 (14)	0.0006 (11)	0.0107 (11)	−0.0017 (11)
C6	0.0318 (14)	0.0377 (16)	0.0287 (14)	0.0005 (12)	0.0113 (12)	−0.0038 (12)
C7	0.0275 (13)	0.0268 (14)	0.0242 (13)	0.0022 (11)	0.0129 (11)	0.0037 (11)
C8	0.0296 (14)	0.0297 (15)	0.0310 (14)	0.0024 (11)	0.0114 (11)	−0.0023 (12)
C9	0.0326 (15)	0.0304 (15)	0.0365 (15)	−0.0035 (12)	0.0119 (12)	−0.0050 (12)
C10	0.0238 (13)	0.0362 (16)	0.0303 (14)	0.0009 (11)	0.0071 (11)	0.0056 (12)
C11	0.0319 (15)	0.0313 (15)	0.0336 (15)	0.0065 (12)	0.0153 (12)	0.0033 (12)
C12	0.0324 (15)	0.0275 (14)	0.0305 (14)	−0.0014 (11)	0.0132 (12)	−0.0029 (11)
C13	0.0214 (13)	0.0275 (14)	0.0266 (13)	−0.0026 (11)	0.0073 (11)	−0.0027 (11)
C14	0.0293 (14)	0.0347 (15)	0.0274 (13)	−0.0023 (12)	0.0135 (11)	0.0008 (12)
C15	0.0276 (14)	0.0294 (15)	0.0384 (15)	0.0008 (11)	0.0105 (12)	0.0015 (12)
C16	0.0230 (13)	0.0312 (15)	0.0351 (14)	−0.0040 (11)	0.0113 (11)	−0.0062 (12)
C17	0.0282 (14)	0.0359 (15)	0.0338 (15)	−0.0041 (12)	0.0159 (12)	−0.0028 (12)
C18	0.0314 (14)	0.0285 (15)	0.0283 (13)	−0.0031 (11)	0.0103 (11)	−0.0012 (11)
C19	0.0377 (16)	0.0459 (17)	0.0542 (17)	0.0025 (13)	0.0250 (14)	−0.0032 (14)

O1—C1	1.227 (3)	C16—C19	1.510 (4)
C1—C2	1.462 (4)	C17—C18	1.386 (3)
C1—C6	1.502 (4)	C2—H2	0.9500
C2—C3	1.348 (3)	C4—H4A	0.9900
C3—C4	1.507 (3)	C4—H4B	0.9900
C3—C7	1.484 (3)	C5—H5	1.0000
C4—C5	1.529 (3)	C6—H6A	0.9900
C5—C6	1.526 (3)	C6—H6B	0.9900
C5—C13	1.514 (3)	C8—H8	0.9500
C7—C8	1.395 (3)	C9—H9	0.9500
C7—C12	1.398 (3)	C10—H10	0.9500
C8—C9	1.378 (4)	C11—H11	0.9500
C9—C10	1.375 (4)	C12—H12	0.9500
C10—C11	1.380 (3)	C14—H14	0.9500
C11—C12	1.382 (4)	C15—H15	0.9500
C13—C14	1.389 (3)	C17—H17	0.9500
C13—C18	1.385 (3)	C18—H18	0.9500
C14—C15	1.386 (3)	C19—H19A	0.9800
C15—C16	1.385 (3)	C19—H19B	0.9800
C16—C17	1.382 (3)	C19—H19C	0.9800
O1—C1—C2	121.0 (2)	C5—C4—H4B	109.00
O1—C1—C6	121.8 (2)	H4A—C4—H4B	108.00
C2—C1—C6	117.3 (2)	C4—C5—H5	107.00
C1—C2—C3	123.3 (2)	C6—C5—H5	107.00
C2—C3—C4	119.4 (2)	C13—C5—H5	107.00
C2—C3—C7	122.4 (2)	C1—C6—H6A	110.00
C4—C3—C7	118.20 (19)	C1—C6—H6B	110.00
C3—C4—C5	112.14 (19)	C5—C6—H6A	110.00
C4—C5—C6	108.40 (19)	C5—C6—H6B	110.00
C4—C5—C13	111.98 (19)	H6A—C6—H6B	108.00
C6—C5—C13	115.3 (2)	C7—C8—H8	119.00
C1—C6—C5	110.00 (19)	C9—C8—H8	119.00
C3—C7—C8	120.8 (2)	C8—C9—H9	119.00
C3—C7—C12	122.3 (2)	C10—C9—H9	119.00
C8—C7—C12	116.9 (2)	C9—C10—H10	121.00
C7—C8—C9	121.3 (2)	C11—C10—H10	121.00
C8—C9—C10	121.0 (2)	C10—C11—H11	120.00
C9—C10—C11	118.9 (2)	C12—C11—H11	120.00
C10—C11—C12	120.3 (2)	C7—C12—H12	119.00
C7—C12—C11	121.6 (2)	C11—C12—H12	119.00
C5—C13—C14	122.4 (2)	C13—C14—H14	120.00
C5—C13—C18	119.9 (2)	C15—C14—H14	120.00
C14—C13—C18	117.6 (2)	C14—C15—H15	119.00
C13—C14—C15	120.8 (2)	C16—C15—H15	119.00
C14—C15—C16	121.6 (2)	C16—C17—H17	119.00
C15—C16—C17	117.6 (2)	C18—C17—H17	119.00
C15—C16—C19	121.6 (2)	C13—C18—H18	119.00
C17—C16—C19	120.8 (2)	C17—C18—H18	119.00
C16—C17—C18	121.1 (2)	C16—C19—H19A	109.00
C13—C18—C17	121.4 (2)	C16—C19—H19B	109.00
C1—C2—H2	118.00	C16—C19—H19C	109.00
C3—C2—H2	118.00	H19A—C19—H19B	110.00
C3—C4—H4A	109.00	H19A—C19—H19C	109.00
C3—C4—H4B	109.00	H19B—C19—H19C	110.00
C5—C4—H4A	109.00
O1—C1—C2—C3	177.4 (2)	C6—C5—C13—C18	−132.9 (2)
C6—C1—C2—C3	−3.0 (3)	C3—C7—C8—C9	−179.8 (2)
O1—C1—C6—C5	−146.2 (2)	C12—C7—C8—C9	−0.3 (3)
C2—C1—C6—C5	34.2 (3)	C3—C7—C12—C11	179.8 (2)
C1—C2—C3—C4	−1.8 (3)	C8—C7—C12—C11	0.3 (3)
C1—C2—C3—C7	178.4 (2)	C7—C8—C9—C10	0.1 (4)
C2—C3—C4—C5	−25.3 (3)	C8—C9—C10—C11	0.0 (4)
C7—C3—C4—C5	154.5 (2)	C9—C10—C11—C12	0.0 (4)
C2—C3—C7—C8	−165.5 (2)	C10—C11—C12—C7	−0.2 (4)
C2—C3—C7—C12	15.0 (4)	C5—C13—C14—C15	177.1 (2)
C4—C3—C7—C8	14.8 (3)	C18—C13—C14—C15	0.2 (4)
C4—C3—C7—C12	−164.7 (2)	C5—C13—C18—C17	−176.7 (2)
C3—C4—C5—C6	55.5 (2)	C14—C13—C18—C17	0.3 (4)
C3—C4—C5—C13	−176.21 (18)	C13—C14—C15—C16	−0.5 (4)
C4—C5—C6—C1	−59.4 (2)	C14—C15—C16—C17	0.4 (4)
C13—C5—C6—C1	174.2 (2)	C14—C15—C16—C19	−179.6 (2)
C4—C5—C13—C14	−74.3 (3)	C15—C16—C17—C18	0.1 (4)
C4—C5—C13—C18	102.5 (2)	C19—C16—C17—C18	−179.9 (2)
C6—C5—C13—C14	50.3 (3)	C16—C17—C18—C13	−0.4 (4)

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10···Cgi	0.95	2.77	3.601 (3)	147

Table 1

Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C13–C18 benzene ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C10—H10⋯Cg i	0.95	2.77	3.601 (3)	147

Symmetry code: (i) .