(3-Benzoyl-phen-yl)(phen-yl)methanone.

Mol-ecules of the title compound, C(20)H(14)O(2), show approximate C(s) symmetry with the approximate mirror plane perpendicular to the central ring. The torsion angles about the acyclic bonds are 30.05 (15) and 30.77 (15)° in one half compared to -36.62 (14) and -18.60 (15)° in the other half of the mol-ecule. The central aromatic ring makes dihedral angles of 47.78 (4) and 51.68 (3)° with the two terminal rings.

Related literature

For background to diaryl­ketones, see: Olah (1964 ▶); Szmant (1989 ▶); March (1992 ▶). For the synthesis of benzoyl­benzene and its derivatives, see: Karrer et al. (2000 ▶); Kowalski et al. (2005 ▶). For its natural occurrence, see: Baggett et al. (2005 ▶); Chiang et al. (2003 ▶); Bernardi, et al. (2005 ▶); Kulanthaivel et al. (1993 ▶); Iijima et al. (2004 ▶). For applications of these compounds, see: Bohm et al. (2001 ▶); Chan et al. (2004 ▶); Bagheri et al. (2000 ▶); Husain et al. (2006 ▶).

Experimental

Crystal data

C20H14O2

M = 286.31

Orthorhombic,

a = 16.2029 (5) Å

b = 7.8648 (4) Å

c = 22.8422 (8) Å

V = 2910.8 (2) Å3

Z = 8

Mo Kα radiation

μ = 0.08 mm−1

T = 173 K

0.45 × 0.45 × 0.43 mm

Data collection

Stoe IPDS II two-circle diffractometer

40513 measured reflections

3653 independent reflections

3095 reflections with I > 2σ(I)

R int = 0.050

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.101

S = 1.05

3653 reflections

200 parameters

H-atom parameters constrained

Δρmax = 0.28 e Å−3

Δρmin = −0.15 e Å−3

Data collection: X-AREA (Stoe & Cie, 2001 ▶); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: XP in SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811033344/fy2021sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811033344/fy2021Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811033344/fy2021Isup3.cml

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

C20H14O2	F(000) = 1200
Mr = 286.31	Dx = 1.307 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 32870 reflections
a = 16.2029 (5) Å	θ = 2.7–28.7°
b = 7.8648 (4) Å	µ = 0.08 mm−1
c = 22.8422 (8) Å	T = 173 K
V = 2910.8 (2) Å3	Block, colourless
Z = 8	0.45 × 0.45 × 0.43 mm

Stoe IPDS II two-circle diffractometer	3095 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.050
graphite	θmax = 28.4°, θmin = 3.0°
ω scans	h = −21→21
40513 measured reflections	k = −10→10
3653 independent reflections	l = −29→30

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.037	H-atom parameters constrained
wR(F2) = 0.101	w = 1/[σ2(Fo2) + (0.0547P)2 + 0.4425P] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max = 0.001
3653 reflections	Δρmax = 0.28 e Å−3
200 parameters	Δρmin = −0.15 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0128 (12)

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.

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
O1	0.57553 (5)	0.26790 (13)	0.50072 (4)	0.0480 (2)
O2	0.72489 (5)	0.52781 (15)	0.23112 (4)	0.0539 (3)
C1	0.60337 (6)	0.42835 (12)	0.41666 (4)	0.0262 (2)
C2	0.60051 (6)	0.42295 (12)	0.35545 (4)	0.0259 (2)
H2	0.5597	0.3564	0.3363	0.031*
C3	0.65756 (6)	0.51526 (13)	0.32241 (4)	0.0286 (2)
C4	0.71769 (6)	0.61245 (13)	0.35094 (5)	0.0334 (2)
H4	0.7570	0.6743	0.3286	0.040*
C5	0.72029 (7)	0.61901 (13)	0.41153 (5)	0.0347 (2)
H5	0.7607	0.6866	0.4306	0.042*
C6	0.66382 (6)	0.52687 (13)	0.44426 (5)	0.0304 (2)
H6	0.6662	0.5306	0.4858	0.036*
C7	0.54757 (6)	0.32464 (13)	0.45492 (4)	0.0293 (2)
C8	0.65929 (7)	0.50879 (14)	0.25675 (5)	0.0338 (2)
C11	0.45990 (6)	0.29171 (12)	0.43842 (4)	0.0268 (2)
C12	0.41725 (6)	0.38926 (13)	0.39722 (4)	0.0303 (2)
H12	0.4445	0.4802	0.3778	0.036*
C13	0.33493 (7)	0.35381 (15)	0.38441 (5)	0.0365 (2)
H13	0.3063	0.4198	0.3561	0.044*
C14	0.29496 (7)	0.22188 (15)	0.41305 (6)	0.0400 (3)
H14	0.2388	0.1978	0.4044	0.048*
C15	0.33652 (7)	0.12507 (14)	0.45422 (5)	0.0378 (3)
H15	0.3089	0.0347	0.4736	0.045*
C16	0.41827 (6)	0.15987 (13)	0.46714 (5)	0.0312 (2)
H16	0.4463	0.0938	0.4957	0.037*
C21	0.58125 (6)	0.47839 (13)	0.22351 (4)	0.0300 (2)
C22	0.50446 (7)	0.53230 (13)	0.24428 (5)	0.0313 (2)
H22	0.5006	0.5873	0.2812	0.038*
C23	0.43365 (7)	0.50573 (15)	0.21107 (5)	0.0371 (2)
H23	0.3815	0.5417	0.2254	0.044*
C24	0.43937 (8)	0.42670 (15)	0.15702 (5)	0.0400 (3)
H24	0.3910	0.4086	0.1344	0.048*
C25	0.51537 (9)	0.37388 (15)	0.13580 (5)	0.0414 (3)
H25	0.5190	0.3199	0.0987	0.050*
C26	0.58596 (8)	0.39992 (15)	0.16880 (5)	0.0375 (3)
H26	0.6380	0.3641	0.1541	0.045*

	U11	U22	U33	U12	U13	U23
O1	0.0428 (5)	0.0614 (6)	0.0398 (5)	−0.0123 (4)	−0.0126 (4)	0.0191 (4)
O2	0.0303 (4)	0.0890 (7)	0.0425 (5)	−0.0035 (4)	0.0115 (4)	0.0008 (5)
C1	0.0234 (4)	0.0247 (4)	0.0305 (5)	0.0028 (3)	−0.0006 (4)	−0.0009 (4)
C2	0.0228 (4)	0.0243 (4)	0.0307 (5)	0.0014 (3)	−0.0005 (4)	−0.0021 (4)
C3	0.0241 (5)	0.0278 (5)	0.0338 (5)	0.0032 (4)	0.0029 (4)	−0.0005 (4)
C4	0.0251 (5)	0.0303 (5)	0.0448 (6)	−0.0021 (4)	0.0041 (4)	−0.0002 (4)
C5	0.0273 (5)	0.0323 (5)	0.0444 (6)	−0.0034 (4)	−0.0023 (4)	−0.0075 (4)
C6	0.0268 (5)	0.0308 (5)	0.0336 (5)	0.0027 (4)	−0.0029 (4)	−0.0049 (4)
C7	0.0290 (5)	0.0301 (5)	0.0287 (5)	−0.0004 (4)	−0.0017 (4)	0.0011 (4)
C8	0.0283 (5)	0.0387 (5)	0.0344 (5)	0.0019 (4)	0.0063 (4)	0.0018 (4)
C11	0.0256 (5)	0.0274 (4)	0.0273 (4)	0.0014 (4)	0.0024 (3)	−0.0031 (4)
C12	0.0285 (5)	0.0316 (5)	0.0310 (5)	0.0020 (4)	0.0018 (4)	0.0003 (4)
C13	0.0298 (5)	0.0404 (6)	0.0393 (6)	0.0054 (4)	−0.0045 (4)	−0.0026 (5)
C14	0.0268 (5)	0.0412 (6)	0.0520 (7)	−0.0019 (4)	−0.0020 (5)	−0.0085 (5)
C15	0.0321 (5)	0.0326 (5)	0.0487 (6)	−0.0049 (4)	0.0081 (5)	−0.0024 (5)
C16	0.0311 (5)	0.0285 (5)	0.0340 (5)	0.0014 (4)	0.0039 (4)	0.0002 (4)
C21	0.0314 (5)	0.0305 (5)	0.0282 (5)	−0.0004 (4)	0.0046 (4)	0.0032 (4)
C22	0.0315 (5)	0.0325 (5)	0.0299 (5)	0.0023 (4)	0.0019 (4)	0.0011 (4)
C23	0.0328 (5)	0.0389 (6)	0.0394 (6)	−0.0002 (4)	−0.0020 (4)	0.0079 (5)
C24	0.0467 (7)	0.0364 (6)	0.0369 (5)	−0.0107 (5)	−0.0092 (5)	0.0086 (5)
C25	0.0601 (8)	0.0362 (6)	0.0278 (5)	−0.0078 (5)	0.0007 (5)	0.0007 (4)
C26	0.0435 (6)	0.0388 (6)	0.0302 (5)	0.0000 (5)	0.0097 (4)	0.0011 (4)

O1—C7	1.2242 (12)	C12—H12	0.9500
O2—C8	1.2227 (13)	C13—C14	1.3870 (17)
C1—C6	1.3989 (14)	C13—H13	0.9500
C1—C2	1.3995 (13)	C14—C15	1.3847 (17)
C1—C7	1.4990 (14)	C14—H14	0.9500
C2—C3	1.3969 (14)	C15—C16	1.3844 (15)
C2—H2	0.9500	C15—H15	0.9500
C3—C4	1.3993 (15)	C16—H16	0.9500
C3—C8	1.5009 (15)	C21—C26	1.3958 (15)
C4—C5	1.3857 (16)	C21—C22	1.3975 (14)
C4—H4	0.9500	C22—C23	1.3913 (16)
C5—C6	1.3861 (15)	C22—H22	0.9500
C5—H5	0.9500	C23—C24	1.3852 (17)
C6—H6	0.9500	C23—H23	0.9500
C7—C11	1.4923 (14)	C24—C25	1.3870 (19)
C8—C21	1.4942 (15)	C24—H24	0.9500
C11—C12	1.3970 (14)	C25—C26	1.3851 (18)
C11—C16	1.4002 (14)	C25—H25	0.9500
C12—C13	1.3937 (15)	C26—H26	0.9500
C6—C1—C2	119.36 (9)	C14—C13—C12	119.83 (10)
C6—C1—C7	117.45 (9)	C14—C13—H13	120.1
C2—C1—C7	123.09 (9)	C12—C13—H13	120.1
C3—C2—C1	120.13 (9)	C15—C14—C13	120.31 (10)
C3—C2—H2	119.9	C15—C14—H14	119.8
C1—C2—H2	119.9	C13—C14—H14	119.8
C2—C3—C4	119.54 (9)	C16—C15—C14	120.09 (10)
C2—C3—C8	122.32 (9)	C16—C15—H15	120.0
C4—C3—C8	118.09 (9)	C14—C15—H15	120.0
C5—C4—C3	120.44 (10)	C15—C16—C11	120.49 (10)
C5—C4—H4	119.8	C15—C16—H16	119.8
C3—C4—H4	119.8	C11—C16—H16	119.8
C4—C5—C6	119.95 (10)	C26—C21—C22	119.12 (10)
C4—C5—H5	120.0	C26—C21—C8	118.65 (10)
C6—C5—H5	120.0	C22—C21—C8	122.17 (9)
C5—C6—C1	120.57 (10)	C23—C22—C21	120.23 (10)
C5—C6—H6	119.7	C23—C22—H22	119.9
C1—C6—H6	119.7	C21—C22—H22	119.9
O1—C7—C11	120.32 (9)	C24—C23—C22	119.88 (11)
O1—C7—C1	118.25 (9)	C24—C23—H23	120.1
C11—C7—C1	121.42 (8)	C22—C23—H23	120.1
O2—C8—C21	120.79 (10)	C23—C24—C25	120.34 (11)
O2—C8—C3	119.38 (10)	C23—C24—H24	119.8
C21—C8—C3	119.83 (9)	C25—C24—H24	119.8
C12—C11—C16	118.95 (9)	C26—C25—C24	119.91 (10)
C12—C11—C7	123.07 (9)	C26—C25—H25	120.0
C16—C11—C7	117.95 (9)	C24—C25—H25	120.0
C13—C12—C11	120.33 (10)	C25—C26—C21	120.50 (11)
C13—C12—H12	119.8	C25—C26—H26	119.8
C11—C12—H12	119.8	C21—C26—H26	119.8
C6—C1—C2—C3	−0.02 (14)	C1—C7—C11—C16	163.41 (9)
C7—C1—C2—C3	−176.19 (9)	C16—C11—C12—C13	−0.95 (15)
C1—C2—C3—C4	0.26 (14)	C7—C11—C12—C13	−178.93 (10)
C1—C2—C3—C8	177.63 (9)	C11—C12—C13—C14	0.51 (16)
C2—C3—C4—C5	−0.73 (15)	C12—C13—C14—C15	−0.12 (17)
C8—C3—C4—C5	−178.22 (9)	C13—C14—C15—C16	0.18 (17)
C3—C4—C5—C6	0.96 (16)	C14—C15—C16—C11	−0.63 (16)
C4—C5—C6—C1	−0.72 (16)	C12—C11—C16—C15	1.01 (15)
C2—C1—C6—C5	0.25 (15)	C7—C11—C16—C15	179.09 (10)
C7—C1—C6—C5	176.64 (9)	O2—C8—C21—C26	27.69 (16)
C6—C1—C7—O1	−32.33 (14)	C3—C8—C21—C26	−151.99 (10)
C2—C1—C7—O1	143.91 (11)	O2—C8—C21—C22	−149.55 (12)
C6—C1—C7—C11	147.13 (9)	C3—C8—C21—C22	30.77 (15)
C2—C1—C7—C11	−36.62 (14)	C26—C21—C22—C23	0.87 (15)
C2—C3—C8—O2	−149.63 (11)	C8—C21—C22—C23	178.10 (10)
C4—C3—C8—O2	27.79 (16)	C21—C22—C23—C24	−0.48 (16)
C2—C3—C8—C21	30.05 (15)	C22—C23—C24—C25	−0.01 (17)
C4—C3—C8—C21	−152.53 (10)	C23—C24—C25—C26	0.11 (17)
O1—C7—C11—C12	160.85 (11)	C24—C25—C26—C21	0.30 (17)
C1—C7—C11—C12	−18.60 (15)	C22—C21—C26—C25	−0.78 (16)
O1—C7—C11—C16	−17.14 (15)	C8—C21—C26—C25	−178.11 (10)