[2-(4-Methylbenzoyl)phenyl](4-methylphenyl)methanone.

The asymmetric unit of the title compound, C(22)H(18)O(2), contains one half-mol-ecule, the complete mol-ecule being generated by the operation of a crystallographic twofold rotation axis. The carbonyl group and the two C atoms attached to it forms inter-planar angles of 23.67 (7)° with the methyl-substituted phenyl ring and 50.74 (8)° with the central ring. In the crystal, mol-ecules are linked into infinite chains along the b-axis direction by inter-molecular C-H⋯O inter-actions, generating R(2) (2)(10) graph-set motifs.

Related literature

For the uses and biological importance of diketones, see: Bennett et al. (1999 ▶); Sato et al. (2008 ▶). For related structures, see: Muto et al. (2010 ▶); Khan et al. (2009 ▶); For asymmetry parameters, see: Nardelli (1983 ▶); Macrae et al. (2008 ▶). For graph-set notation: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C22H18O2

M = 314.36

Monoclinic,

a = 20.7432 (13) Å

b = 7.7564 (4) Å

c = 11.3946 (6) Å

β = 114.314 (5)°

V = 1670.70 (17) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 295 K

0.30 × 0.25 × 0.20 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.977, T max = 0.984

17689 measured reflections

2133 independent reflections

1729 reflections with I > 2σ(I)

R int = 0.076

Refinement

R[F 2 > 2σ(F 2)] = 0.050

wR(F 2) = 0.154

S = 1.03

2133 reflections

110 parameters

H-atom parameters constrained

Δρmax = 0.30 e Å−3

Δρmin = −0.28 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); 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 (Farrugia, 1997 ▶) and Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009) ▶.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811028820/rk2284sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811028820/rk2284Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811028820/rk2284Isup3.cml

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

C22H18O2	F(000) = 664
Mr = 314.36	Dx = 1.250 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 2133 reflections
a = 20.7432 (13) Å	θ = 2.2–28.6°
b = 7.7564 (4) Å	µ = 0.08 mm−1
c = 11.3946 (6) Å	T = 295 K
β = 114.314 (5)°	Block, colourless
V = 1670.70 (17) Å3	0.30 × 0.25 × 0.20 mm
Z = 4

Bruker Kappa APEXII CCD diffractometer	2133 independent reflections
Radiation source: fine-focus sealed tube	1729 reflections with I > 2σ(I)
graphite	Rint = 0.076
ω–scans	θmax = 28.6°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −27→27
Tmin = 0.977, Tmax = 0.984	k = −10→10
17689 measured reflections	l = −15→15

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) = 0.154	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0914P)2 + 0.4904P] where P = (Fo2 + 2Fc2)/3
2133 reflections	(Δ/σ)max = 0.005
110 parameters	Δρmax = 0.30 e Å−3
0 restraints	Δρmin = −0.28 e Å−3

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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
C1	0.47990 (8)	−0.45596 (18)	0.68469 (16)	0.0577 (4)
H1	0.4669	−0.5598	0.6403	0.069*
C2	0.45881 (7)	−0.30216 (17)	0.61934 (13)	0.0493 (3)
H2	0.4310	−0.3030	0.5312	0.059*
C3	0.47868 (6)	−0.14603 (15)	0.68400 (11)	0.0375 (3)
C4	0.46029 (6)	0.01963 (15)	0.61000 (11)	0.0380 (3)
C5	0.38557 (6)	0.05007 (15)	0.52013 (11)	0.0384 (3)
C6	0.37060 (7)	0.16656 (18)	0.41976 (13)	0.0478 (3)
H6	0.4074	0.2221	0.4083	0.057*
C7	0.30152 (8)	0.2002 (2)	0.33701 (13)	0.0535 (4)
H7	0.2924	0.2766	0.2691	0.064*
C8	0.24545 (7)	0.12297 (18)	0.35264 (13)	0.0508 (4)
C9	0.26051 (7)	0.0089 (2)	0.45387 (14)	0.0529 (4)
H9	0.2236	−0.0433	0.4668	0.063*
C10	0.32965 (7)	−0.02856 (18)	0.53609 (13)	0.0474 (3)
H10	0.3387	−0.1072	0.6027	0.057*
C11	0.17032 (9)	0.1623 (3)	0.26113 (19)	0.0739 (5)
H11A	0.1696	0.2622	0.2109	0.111*
H11B	0.1425	0.1841	0.3093	0.111*
H11C	0.1509	0.0656	0.2050	0.111*
O1	0.50637 (5)	0.12345 (12)	0.62240 (9)	0.0503 (3)

	U11	U22	U33	U12	U13	U23
C1	0.0579 (8)	0.0333 (6)	0.0742 (10)	−0.0053 (6)	0.0195 (7)	−0.0101 (6)
C2	0.0496 (7)	0.0405 (7)	0.0470 (7)	−0.0063 (5)	0.0091 (6)	−0.0084 (5)
C3	0.0360 (5)	0.0337 (6)	0.0368 (6)	−0.0015 (4)	0.0088 (5)	−0.0008 (4)
C4	0.0414 (6)	0.0359 (6)	0.0318 (6)	−0.0023 (4)	0.0100 (5)	−0.0016 (4)
C5	0.0405 (6)	0.0371 (6)	0.0324 (6)	0.0011 (4)	0.0097 (5)	−0.0003 (4)
C6	0.0487 (7)	0.0482 (7)	0.0442 (7)	0.0033 (5)	0.0167 (6)	0.0096 (5)
C7	0.0557 (8)	0.0531 (8)	0.0437 (7)	0.0116 (6)	0.0125 (6)	0.0121 (6)
C8	0.0450 (7)	0.0493 (7)	0.0471 (7)	0.0084 (6)	0.0079 (6)	−0.0061 (5)
C9	0.0418 (7)	0.0575 (8)	0.0566 (8)	−0.0040 (6)	0.0176 (6)	−0.0025 (6)
C10	0.0484 (7)	0.0482 (7)	0.0416 (7)	−0.0025 (5)	0.0143 (5)	0.0049 (5)
C11	0.0483 (8)	0.0751 (11)	0.0757 (11)	0.0150 (7)	0.0028 (8)	−0.0027 (9)
O1	0.0479 (5)	0.0442 (5)	0.0487 (5)	−0.0100 (4)	0.0098 (4)	0.0032 (4)

C1—C1i	1.374 (3)	C6—H6	0.9300
C1—C2	1.379 (2)	C7—C8	1.383 (2)
C1—H1	0.9300	C7—H7	0.9300
C2—C3	1.3890 (16)	C8—C9	1.384 (2)
C2—H2	0.9300	C8—C11	1.507 (2)
C3—C3i	1.396 (2)	C9—C10	1.383 (2)
C3—C4	1.4975 (16)	C9—H9	0.9300
C4—O1	1.2128 (15)	C10—H10	0.9300
C4—C5	1.4832 (16)	C11—H11A	0.9600
C5—C10	1.3872 (18)	C11—H11B	0.9600
C5—C6	1.3887 (17)	C11—H11C	0.9600
C6—C7	1.3778 (19)
C1i—C1—C2	120.07 (8)	C6—C7—C8	121.50 (13)
C1i—C1—H1	120.0	C6—C7—H7	119.2
C2—C1—H1	120.0	C8—C7—H7	119.2
C1—C2—C3	120.60 (12)	C7—C8—C9	118.11 (12)
C1—C2—H2	119.7	C7—C8—C11	120.53 (14)
C3—C2—H2	119.7	C9—C8—C11	121.36 (15)
C2—C3—C3i	119.31 (7)	C10—C9—C8	120.95 (13)
C2—C3—C4	119.89 (10)	C10—C9—H9	119.5
C3i—C3—C4	120.54 (6)	C8—C9—H9	119.5
O1—C4—C5	121.61 (11)	C9—C10—C5	120.58 (12)
O1—C4—C3	119.89 (10)	C9—C10—H10	119.7
C5—C4—C3	118.48 (10)	C5—C10—H10	119.7
C10—C5—C6	118.59 (11)	C8—C11—H11A	109.5
C10—C5—C4	122.14 (11)	C8—C11—H11B	109.5
C6—C5—C4	119.21 (11)	H11A—C11—H11B	109.5
C7—C6—C5	120.25 (13)	C8—C11—H11C	109.5
C7—C6—H6	119.9	H11A—C11—H11C	109.5
C5—C6—H6	119.9	H11B—C11—H11C	109.5
C1i—C1—C2—C3	1.0 (3)	C10—C5—C6—C7	−1.1 (2)
C1—C2—C3—C3i	1.0 (2)	C4—C5—C6—C7	−178.36 (12)
C1—C2—C3—C4	175.06 (13)	C5—C6—C7—C8	1.4 (2)
C2—C3—C4—O1	−125.83 (13)	C6—C7—C8—C9	−0.5 (2)
C3i—C3—C4—O1	48.2 (2)	C6—C7—C8—C11	179.79 (14)
C2—C3—C4—C5	52.62 (16)	C7—C8—C9—C10	−0.8 (2)
C3i—C3—C4—C5	−133.37 (15)	C11—C8—C9—C10	178.91 (14)
O1—C4—C5—C10	−156.10 (13)	C8—C9—C10—C5	1.2 (2)
C3—C4—C5—C10	25.47 (17)	C6—C5—C10—C9	−0.2 (2)
O1—C4—C5—C6	21.08 (18)	C4—C5—C10—C9	177.00 (12)
C3—C4—C5—C6	−157.35 (12)

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1···O1ii	0.93	2.62	3.4305 (17)	145.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1⋯O1i	0.93	2.62	3.4305 (17)	145

Symmetry code: (i) .