(2-Benzoyl-phen-yl)(3,4-dimethyl-phen-yl)methanone.

In the title compound, C(22)H(18)O(2), the central benzene ring forms dihedral angles of 76.0 (1) and 73.1 (1)° with the phenyl ring and dimethyl-substituted benzene ring, respectively. The carbonyl-group O atoms deviate significantly from the phenyl ring and the dimethyl-substituted benzene ring [-0.582 (12) and 0.546 (12) Å, respectively]. The crystal packing is stabilized by C-H⋯π inter-actions.

Related literature

For the synthesis of heterocyclic compounds, see: Hirsch & Bailey (1978 ▶). For chelating reagents of metallic systems, see: Liang et al. (2003 ▶). For related bond-length and angle values, see: Judaš & Kaitner (2005) ▶. For related structures, see: Khan et al. (2009 ▶); Narayanan et al. (2011 ▶).

Experimental

Crystal data

C22H18O2

M = 314.36

Monoclinic,

a = 17.8606 (14) Å

b = 7.7590 (6) Å

c = 11.9722 (11) Å

β = 93.942 (3)°

V = 1655.2 (2) 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

17270 measured reflections

3862 independent reflections

2827 reflections with I > 2σ(I)

R int = 0.030

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.129

S = 1.01

3862 reflections

219 parameters

H-atom parameters constrained

Δρmax = 0.22 e Å−3

Δρmin = −0.18 e Å−3

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT (Bruker, 2008 ▶); 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 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811029965/rk2286sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811029965/rk2286Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811029965/rk2286Isup3.cml

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

C22H18O2	F(000) = 664
Mr = 314.36	Dx = 1.262 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3862 reflections
a = 17.8606 (14) Å	θ = 2.3–27.7°
b = 7.7590 (6) Å	µ = 0.08 mm−1
c = 11.9722 (11) Å	T = 295 K
β = 93.942 (3)°	Block, colourless
V = 1655.2 (2) Å3	0.30 × 0.25 × 0.20 mm
Z = 4

Bruker Kappa APEXII CCD diffractometer	2827 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.030
graphite	θmax = 27.7°, θmin = 2.3°
ω scans	h = −23→21
17270 measured reflections	k = −10→10
3862 independent 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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.129	H-atom parameters constrained
S = 1.01	w = 1/[σ2(Fo2) + (0.0581P)2 + 0.4044P] where P = (Fo2 + 2Fc2)/3
3862 reflections	(Δ/σ)max < 0.001
219 parameters	Δρmax = 0.22 e Å−3
0 restraints	Δρmin = −0.18 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	0.05252 (9)	0.7620 (2)	1.04279 (14)	0.0501 (4)
H1	0.0669	0.8384	0.9884	0.060*
C2	−0.02238 (9)	0.7235 (3)	1.04997 (17)	0.0655 (5)
H2	−0.0582	0.7729	0.9998	0.079*
C3	−0.04421 (11)	0.6128 (3)	1.1308 (2)	0.0731 (6)
H3	−0.0948	0.5871	1.1354	0.088*
C4	0.00862 (12)	0.5398 (3)	1.20492 (18)	0.0722 (6)
H4	−0.0064	0.4659	1.2603	0.087*
C5	0.08396 (10)	0.5754 (2)	1.19788 (14)	0.0555 (4)
H5	0.1196	0.5245	1.2477	0.067*
C6	0.10627 (8)	0.68748 (18)	1.11613 (12)	0.0397 (3)
C7	0.18732 (8)	0.71909 (18)	1.10391 (11)	0.0375 (3)
C8	0.20890 (7)	0.88500 (17)	1.05002 (12)	0.0361 (3)
C9	0.19085 (8)	1.04058 (19)	1.09856 (14)	0.0481 (4)
H9	0.1628	1.0414	1.1612	0.058*
C10	0.21426 (9)	1.1940 (2)	1.05444 (17)	0.0579 (5)
H10	0.2032	1.2977	1.0887	0.070*
C11	0.25395 (9)	1.1945 (2)	0.95989 (18)	0.0607 (5)
H11	0.2678	1.2984	0.9285	0.073*
C12	0.27318 (8)	1.04049 (19)	0.91177 (15)	0.0516 (4)
H12	0.3010	1.0412	0.8489	0.062*
C13	0.25147 (7)	0.88492 (17)	0.95623 (12)	0.0377 (3)
C14	0.26870 (7)	0.71987 (17)	0.89837 (11)	0.0364 (3)
C15	0.34810 (7)	0.68460 (16)	0.87551 (11)	0.0338 (3)
C16	0.40683 (7)	0.74660 (17)	0.94594 (11)	0.0343 (3)
H16	0.3961	0.8163	1.0060	0.041*
C17	0.48140 (7)	0.70753 (16)	0.92943 (11)	0.0343 (3)
C18	0.49709 (8)	0.60617 (17)	0.83744 (11)	0.0363 (3)
C19	0.43783 (8)	0.54581 (18)	0.76678 (11)	0.0412 (3)
H19	0.4482	0.4791	0.7052	0.049*
C20	0.36435 (8)	0.58169 (18)	0.78516 (11)	0.0395 (3)
H20	0.3257	0.5375	0.7375	0.047*
C21	0.57643 (9)	0.5594 (2)	0.81499 (14)	0.0500 (4)
H21A	0.5760	0.4796	0.7537	0.075*
H21B	0.6007	0.5073	0.8806	0.075*
H21C	0.6032	0.6615	0.7964	0.075*
C22	0.54257 (9)	0.7725 (2)	1.00999 (13)	0.0472 (4)
H22A	0.5211	0.8371	1.0682	0.071*
H22B	0.5756	0.8454	0.9712	0.071*
H22C	0.5703	0.6767	1.0423	0.071*
O1	0.21870 (6)	0.61966 (14)	0.87004 (10)	0.0530 (3)
O2	0.23523 (6)	0.61759 (14)	1.13704 (10)	0.0545 (3)

	U11	U22	U33	U12	U13	U23
C1	0.0392 (8)	0.0533 (9)	0.0576 (9)	−0.0033 (7)	0.0023 (7)	0.0058 (7)
C2	0.0382 (9)	0.0726 (12)	0.0846 (13)	−0.0041 (8)	−0.0035 (9)	0.0008 (10)
C3	0.0435 (10)	0.0785 (14)	0.0991 (15)	−0.0173 (9)	0.0185 (10)	−0.0055 (12)
C4	0.0656 (13)	0.0712 (13)	0.0830 (13)	−0.0172 (10)	0.0288 (11)	0.0111 (11)
C5	0.0547 (10)	0.0568 (10)	0.0560 (9)	−0.0037 (8)	0.0110 (8)	0.0100 (8)
C6	0.0370 (7)	0.0390 (7)	0.0436 (7)	−0.0022 (6)	0.0066 (6)	−0.0025 (6)
C7	0.0367 (7)	0.0368 (7)	0.0390 (7)	0.0029 (6)	0.0020 (6)	−0.0020 (6)
C8	0.0263 (6)	0.0331 (7)	0.0485 (8)	0.0009 (5)	−0.0004 (6)	−0.0019 (6)
C9	0.0377 (8)	0.0434 (8)	0.0630 (9)	0.0063 (6)	0.0033 (7)	−0.0088 (7)
C10	0.0392 (8)	0.0334 (8)	0.1004 (14)	0.0050 (7)	−0.0008 (9)	−0.0130 (8)
C11	0.0389 (8)	0.0320 (8)	0.1117 (15)	−0.0032 (7)	0.0077 (9)	0.0111 (9)
C12	0.0362 (8)	0.0408 (8)	0.0791 (11)	−0.0023 (6)	0.0132 (8)	0.0099 (8)
C13	0.0254 (6)	0.0340 (7)	0.0537 (8)	−0.0008 (5)	0.0035 (6)	0.0017 (6)
C14	0.0319 (7)	0.0358 (7)	0.0419 (7)	−0.0028 (6)	0.0048 (6)	0.0031 (6)
C15	0.0323 (7)	0.0313 (6)	0.0382 (7)	−0.0011 (5)	0.0046 (5)	0.0030 (5)
C16	0.0369 (7)	0.0321 (7)	0.0347 (6)	0.0004 (5)	0.0074 (5)	−0.0017 (5)
C17	0.0343 (7)	0.0320 (6)	0.0365 (7)	−0.0009 (5)	0.0027 (5)	0.0047 (5)
C18	0.0370 (7)	0.0336 (7)	0.0394 (7)	0.0045 (6)	0.0091 (6)	0.0066 (5)
C19	0.0477 (8)	0.0401 (8)	0.0366 (7)	0.0035 (6)	0.0080 (6)	−0.0057 (6)
C20	0.0397 (8)	0.0404 (7)	0.0381 (7)	−0.0031 (6)	0.0009 (6)	−0.0031 (6)
C21	0.0418 (8)	0.0538 (9)	0.0557 (9)	0.0106 (7)	0.0122 (7)	0.0022 (7)
C22	0.0397 (8)	0.0523 (9)	0.0489 (8)	−0.0027 (7)	−0.0023 (6)	−0.0010 (7)
O1	0.0388 (6)	0.0506 (7)	0.0701 (7)	−0.0122 (5)	0.0088 (5)	−0.0117 (5)
O2	0.0459 (6)	0.0471 (6)	0.0703 (7)	0.0103 (5)	0.0029 (5)	0.0112 (5)

C1—C2	1.379 (2)	C12—C13	1.3853 (19)
C1—C6	1.382 (2)	C12—H12	0.9300
C1—H1	0.9300	C13—C14	1.4980 (19)
C2—C3	1.371 (3)	C14—O1	1.2146 (16)
C2—H2	0.9300	C14—C15	1.4880 (18)
C3—C4	1.372 (3)	C15—C16	1.3861 (19)
C3—H3	0.9300	C15—C20	1.3911 (18)
C4—C5	1.382 (3)	C16—C17	1.3932 (18)
C4—H4	0.9300	C16—H16	0.9300
C5—C6	1.388 (2)	C17—C18	1.3973 (18)
C5—H5	0.9300	C17—C22	1.494 (2)
C6—C7	1.4854 (19)	C18—C19	1.390 (2)
C7—O2	1.2095 (17)	C18—C21	1.5046 (19)
C7—C8	1.5020 (19)	C19—C20	1.374 (2)
C8—C9	1.3873 (19)	C19—H19	0.9300
C8—C13	1.399 (2)	C20—H20	0.9300
C9—C10	1.379 (2)	C21—H21A	0.9600
C9—H9	0.9300	C21—H21B	0.9600
C10—C11	1.376 (3)	C21—H21C	0.9600
C10—H10	0.9300	C22—H22A	0.9600
C11—C12	1.380 (2)	C22—H22B	0.9600
C11—H11	0.9300	C22—H22C	0.9600
C2—C1—C6	120.27 (16)	C12—C13—C8	119.34 (13)
C2—C1—H1	119.9	C12—C13—C14	119.69 (13)
C6—C1—H1	119.9	C8—C13—C14	120.79 (12)
C3—C2—C1	120.25 (18)	O1—C14—C15	121.51 (12)
C3—C2—H2	119.9	O1—C14—C13	120.39 (12)
C1—C2—H2	119.9	C15—C14—C13	118.09 (11)
C2—C3—C4	119.92 (17)	C16—C15—C20	118.85 (12)
C2—C3—H3	120.0	C16—C15—C14	121.02 (12)
C4—C3—H3	120.0	C20—C15—C14	120.07 (12)
C3—C4—C5	120.49 (18)	C15—C16—C17	121.94 (12)
C3—C4—H4	119.8	C15—C16—H16	119.0
C5—C4—H4	119.8	C17—C16—H16	119.0
C4—C5—C6	119.76 (17)	C16—C17—C18	118.67 (12)
C4—C5—H5	120.1	C16—C17—C22	119.91 (12)
C6—C5—H5	120.1	C18—C17—C22	121.41 (13)
C1—C6—C5	119.30 (14)	C19—C18—C17	118.93 (12)
C1—C6—C7	120.48 (13)	C19—C18—C21	119.81 (13)
C5—C6—C7	120.13 (14)	C17—C18—C21	121.26 (13)
O2—C7—C6	122.17 (13)	C20—C19—C18	122.01 (13)
O2—C7—C8	120.16 (12)	C20—C19—H19	119.0
C6—C7—C8	117.67 (12)	C18—C19—H19	119.0
C9—C8—C13	119.44 (13)	C19—C20—C15	119.57 (13)
C9—C8—C7	119.47 (13)	C19—C20—H20	120.2
C13—C8—C7	120.94 (11)	C15—C20—H20	120.2
C10—C9—C8	120.37 (15)	C18—C21—H21A	109.5
C10—C9—H9	119.8	C18—C21—H21B	109.5
C8—C9—H9	119.8	H21A—C21—H21B	109.5
C11—C10—C9	120.26 (15)	C18—C21—H21C	109.5
C11—C10—H10	119.9	H21A—C21—H21C	109.5
C9—C10—H10	119.9	H21B—C21—H21C	109.5
C10—C11—C12	119.89 (15)	C17—C22—H22A	109.5
C10—C11—H11	120.1	C17—C22—H22B	109.5
C12—C11—H11	120.1	H22A—C22—H22B	109.5
C11—C12—C13	120.64 (15)	C17—C22—H22C	109.5
C11—C12—H12	119.7	H22A—C22—H22C	109.5
C13—C12—H12	119.7	H22B—C22—H22C	109.5
C6—C1—C2—C3	0.8 (3)	C7—C8—C13—C12	−177.13 (13)
C1—C2—C3—C4	0.0 (3)	C9—C8—C13—C14	−176.94 (13)
C2—C3—C4—C5	−0.8 (3)	C7—C8—C13—C14	7.6 (2)
C3—C4—C5—C6	0.8 (3)	C12—C13—C14—O1	−124.06 (16)
C2—C1—C6—C5	−0.8 (2)	C8—C13—C14—O1	51.2 (2)
C2—C1—C6—C7	175.82 (15)	C12—C13—C14—C15	55.03 (18)
C4—C5—C6—C1	0.0 (3)	C8—C13—C14—C15	−129.72 (14)
C4—C5—C6—C7	−176.65 (16)	O1—C14—C15—C16	−150.17 (14)
C1—C6—C7—O2	−153.93 (15)	C13—C14—C15—C16	30.75 (18)
C5—C6—C7—O2	22.7 (2)	O1—C14—C15—C20	27.0 (2)
C1—C6—C7—C8	27.09 (19)	C13—C14—C15—C20	−152.12 (13)
C5—C6—C7—C8	−156.27 (14)	C20—C15—C16—C17	−0.6 (2)
O2—C7—C8—C9	−118.70 (16)	C14—C15—C16—C17	176.55 (12)
C6—C7—C8—C9	60.30 (17)	C15—C16—C17—C18	1.55 (19)
O2—C7—C8—C13	56.75 (19)	C15—C16—C17—C22	−177.87 (13)
C6—C7—C8—C13	−124.25 (14)	C16—C17—C18—C19	−0.98 (19)
C13—C8—C9—C10	0.4 (2)	C22—C17—C18—C19	178.44 (13)
C7—C8—C9—C10	175.91 (14)	C16—C17—C18—C21	−179.98 (12)
C8—C9—C10—C11	1.8 (2)	C22—C17—C18—C21	−0.6 (2)
C9—C10—C11—C12	−2.8 (3)	C17—C18—C19—C20	−0.5 (2)
C10—C11—C12—C13	1.5 (3)	C21—C18—C19—C20	178.50 (13)
C11—C12—C13—C8	0.8 (2)	C18—C19—C20—C15	1.5 (2)
C11—C12—C13—C14	176.08 (15)	C16—C15—C20—C19	−0.9 (2)
C9—C8—C13—C12	−1.7 (2)	C14—C15—C20—C19	−178.09 (12)

Cg1 is the centroid of the C1–C6 ring and Cg3 is the centroid of the C15–C20 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···Cg1i	0.93	2.86	3.747 (2)	159
C21—H21A···Cg3ii	0.96	2.91	3.8144 (17)	157
C22—H22C···Cg3iii	0.96	2.78	3.6484 (17)	152

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C1–C6 ring and Cg3 is the centroid of the C15–C20 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4—H4⋯Cg1i	0.93	2.86	3.747 (2)	159
C21—H21A⋯Cg3ii	0.96	2.91	3.8144 (17)	157
C22—H22C⋯Cg3iii	0.96	2.78	3.6484 (17)	152

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