(Biphenyl-4-yl)[2-(4-methyl-benzo-yl)phen-yl]methanone.

In the title compound, C(27)H(20)O(2), the central benzene ring makes dihedral angles of 64.86 (7) and 70.35 (7)° with the methyl-substituted ring and the biphenyl ring system, respectively. The crystal packing is stabilized by inter-molecular C-H⋯O inter-actions, which link the mol-ecules into chains parallel to the b axis.

Related literature

For the uses and biological importance of diketones, see: Bennett et al. (1999 ▶); Sato et al. (2008 ▶). For applications of biphenyl derivatives, see: Kucybala & Wrzyszczynski (2002 ▶). For related structures, see: Narayanan et al. (2011 ▶); Saeed et al. (2010 ▶).

Experimental

Crystal data

C27H20O2

M = 376.43

Monoclinic,

a = 22.2591 (5) Å

b = 7.7624 (2) Å

c = 11.4312 (2) Å

β = 97.454 (1)°

V = 1958.44 (8) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 293 K

0.20 × 0.20 × 0.20 mm

Data collection

Bruker SMART APEXII area-detector diffractometer

18479 measured reflections

4860 independent reflections

3695 reflections with I > 2σ(I)

R int = 0.032

Refinement

R[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.147

S = 1.01

4860 reflections

264 parameters

H-atom parameters constrained

Δρmax = 0.26 e Å−3

Δρmin = −0.20 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) global, I. DOI: 10.1107/S1600536811047131/bt5706sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811047131/bt5706Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811047131/bt5706Isup3.cml

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

C27H20O2	F(000) = 792
Mr = 376.43	Dx = 1.277 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4860 reflections
a = 22.2591 (5) Å	θ = 1.9–28.3°
b = 7.7624 (2) Å	µ = 0.08 mm−1
c = 11.4312 (2) Å	T = 293 K
β = 97.454 (1)°	Block, colourless
V = 1958.44 (8) Å3	0.20 × 0.20 × 0.20 mm
Z = 4

Bruker SMART APEXII area-detector diffractometer	3695 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.032
graphite	θmax = 28.3°, θmin = 1.9°
ω and φ scans	h = −29→29
18479 measured reflections	k = −10→10
4860 independent reflections	l = −14→15

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)] = 0.047	H-atom parameters constrained
wR(F2) = 0.147	w = 1/[σ2(Fo2) + (0.0727P)2 + 0.5102P] where P = (Fo2 + 2Fc2)/3
S = 1.01	(Δ/σ)max = 0.030
4860 reflections	Δρmax = 0.26 e Å−3
264 parameters	Δρmin = −0.20 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: 0.0107 (16)

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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	0.28534 (5)	0.38124 (13)	0.65595 (10)	0.0506 (3)
C13	0.24874 (6)	0.27565 (17)	0.61339 (11)	0.0377 (3)
O2	0.28106 (5)	0.38387 (14)	0.38609 (10)	0.0544 (3)
C14	0.26900 (5)	0.11095 (16)	0.56107 (12)	0.0375 (3)
C7	0.05660 (6)	0.33333 (17)	0.61684 (12)	0.0392 (3)
C20	0.32077 (6)	0.27867 (17)	0.41439 (12)	0.0409 (3)
C21	0.38428 (6)	0.30892 (17)	0.39267 (12)	0.0405 (3)
C10	0.18236 (6)	0.29702 (17)	0.61430 (11)	0.0386 (3)
C19	0.30593 (6)	0.11233 (17)	0.47073 (13)	0.0410 (3)
C4	−0.01000 (6)	0.34472 (17)	0.62034 (12)	0.0404 (3)
C18	0.32434 (7)	−0.0436 (2)	0.42671 (16)	0.0544 (4)
H18	0.3481	−0.0438	0.3655	0.065*
C11	0.14137 (7)	0.2168 (2)	0.53081 (13)	0.0527 (4)
H11	0.1554	0.1489	0.4731	0.063*
C9	0.16008 (7)	0.4010 (2)	0.69754 (14)	0.0507 (4)
H9	0.1868	0.4602	0.7526	0.061*
C15	0.25338 (6)	−0.04573 (18)	0.60771 (14)	0.0472 (3)
H15	0.2293	−0.0472	0.6684	0.057*
C25	0.45437 (7)	0.4572 (2)	0.28431 (14)	0.0530 (4)
H25	0.4610	0.5322	0.2238	0.064*
C22	0.43345 (7)	0.2315 (2)	0.46015 (13)	0.0482 (3)
H22	0.4268	0.1541	0.5192	0.058*
C23	0.49216 (7)	0.2685 (2)	0.44031 (15)	0.0531 (4)
H23	0.5245	0.2170	0.4873	0.064*
C17	0.30771 (8)	−0.1976 (2)	0.47294 (18)	0.0609 (5)
H17	0.3198	−0.3009	0.4421	0.073*
C8	0.09836 (7)	0.4172 (2)	0.69900 (14)	0.0536 (4)
H8	0.0843	0.4860	0.7563	0.064*
C26	0.39563 (7)	0.4241 (2)	0.30508 (13)	0.0485 (3)
H26	0.3635	0.4793	0.2601	0.058*
C24	0.50361 (7)	0.3812 (2)	0.35152 (14)	0.0497 (4)
C12	0.07980 (7)	0.2361 (2)	0.53183 (14)	0.0544 (4)
H12	0.0532	0.1822	0.4737	0.065*
C16	0.27311 (7)	−0.19908 (19)	0.56502 (17)	0.0573 (4)
H16	0.2632	−0.3031	0.5980	0.069*
C5	−0.05078 (8)	0.2644 (3)	0.53690 (18)	0.0706 (5)
H5	−0.0363	0.2027	0.4766	0.085*
C3	−0.03413 (8)	0.4333 (3)	0.70758 (17)	0.0674 (5)
H3	−0.0082	0.4883	0.7663	0.081*
C1	−0.13564 (7)	0.3628 (2)	0.62571 (17)	0.0599 (4)
H1	−0.1773	0.3700	0.6269	0.072*
C2	−0.09621 (8)	0.4423 (3)	0.7099 (2)	0.0786 (6)
H2	−0.1112	0.5036	0.7698	0.094*
C27	0.56713 (8)	0.4206 (3)	0.3272 (2)	0.0718 (5)
H27A	0.5789	0.3394	0.2711	0.108*
H27B	0.5944	0.4126	0.3993	0.108*
H27C	0.5685	0.5351	0.2958	0.108*
C6	−0.11250 (8)	0.2728 (3)	0.54021 (19)	0.0753 (6)
H6	−0.1386	0.2159	0.4828	0.090*

	U11	U22	U33	U12	U13	U23
O1	0.0451 (6)	0.0452 (6)	0.0626 (7)	−0.0084 (4)	0.0114 (5)	−0.0064 (5)
C13	0.0380 (6)	0.0378 (7)	0.0384 (6)	−0.0015 (5)	0.0089 (5)	0.0035 (5)
O2	0.0517 (6)	0.0479 (6)	0.0665 (7)	0.0115 (5)	0.0188 (5)	0.0113 (5)
C14	0.0300 (6)	0.0359 (6)	0.0466 (7)	−0.0011 (5)	0.0052 (5)	0.0024 (5)
C7	0.0373 (6)	0.0397 (7)	0.0413 (7)	0.0034 (5)	0.0073 (5)	0.0015 (5)
C20	0.0451 (7)	0.0375 (7)	0.0421 (7)	0.0028 (6)	0.0133 (5)	−0.0010 (5)
C21	0.0432 (7)	0.0384 (7)	0.0417 (7)	−0.0007 (6)	0.0122 (5)	−0.0009 (5)
C10	0.0369 (6)	0.0393 (7)	0.0405 (6)	0.0019 (5)	0.0087 (5)	0.0024 (5)
C19	0.0366 (6)	0.0360 (7)	0.0517 (8)	0.0013 (5)	0.0108 (6)	0.0005 (5)
C4	0.0383 (7)	0.0379 (7)	0.0456 (7)	0.0037 (5)	0.0074 (5)	0.0027 (5)
C18	0.0524 (9)	0.0432 (8)	0.0707 (10)	0.0056 (7)	0.0201 (7)	−0.0062 (7)
C11	0.0422 (7)	0.0691 (10)	0.0469 (8)	0.0090 (7)	0.0060 (6)	−0.0192 (7)
C9	0.0409 (7)	0.0565 (9)	0.0555 (8)	−0.0048 (6)	0.0091 (6)	−0.0179 (7)
C15	0.0370 (7)	0.0426 (8)	0.0625 (9)	−0.0052 (6)	0.0077 (6)	0.0080 (6)
C25	0.0565 (9)	0.0518 (9)	0.0531 (8)	−0.0110 (7)	0.0160 (7)	0.0069 (7)
C22	0.0509 (8)	0.0487 (8)	0.0464 (7)	0.0034 (6)	0.0116 (6)	0.0068 (6)
C23	0.0450 (8)	0.0567 (9)	0.0574 (9)	0.0049 (7)	0.0057 (6)	−0.0004 (7)
C17	0.0544 (9)	0.0353 (8)	0.0933 (13)	0.0058 (7)	0.0102 (9)	−0.0072 (8)
C8	0.0440 (8)	0.0611 (9)	0.0576 (9)	−0.0001 (7)	0.0135 (7)	−0.0221 (7)
C26	0.0485 (8)	0.0493 (8)	0.0478 (8)	−0.0024 (6)	0.0067 (6)	0.0075 (6)
C24	0.0465 (8)	0.0480 (8)	0.0568 (9)	−0.0062 (6)	0.0151 (6)	−0.0105 (7)
C12	0.0401 (7)	0.0729 (11)	0.0483 (8)	0.0061 (7)	−0.0011 (6)	−0.0209 (7)
C16	0.0465 (8)	0.0344 (7)	0.0893 (12)	−0.0049 (6)	0.0021 (8)	0.0105 (7)
C5	0.0442 (9)	0.0904 (14)	0.0785 (12)	−0.0044 (9)	0.0123 (8)	−0.0382 (11)
C3	0.0443 (8)	0.0872 (13)	0.0711 (11)	0.0035 (8)	0.0091 (8)	−0.0318 (10)
C1	0.0381 (7)	0.0653 (10)	0.0778 (11)	0.0021 (7)	0.0130 (7)	0.0006 (9)
C2	0.0476 (9)	0.0999 (16)	0.0911 (14)	0.0064 (10)	0.0200 (9)	−0.0371 (12)
C27	0.0503 (9)	0.0731 (12)	0.0956 (14)	−0.0116 (9)	0.0233 (9)	−0.0098 (11)
C6	0.0417 (9)	0.0968 (15)	0.0863 (13)	−0.0110 (9)	0.0047 (8)	−0.0311 (12)

O1—C13	1.2122 (16)	C25—C26	1.383 (2)
C13—C10	1.4881 (18)	C25—C24	1.386 (2)
C13—C14	1.5052 (18)	C25—H25	0.9300
O2—C20	1.2159 (17)	C22—C23	1.385 (2)
C14—C15	1.3901 (18)	C22—H22	0.9300
C14—C19	1.4009 (19)	C23—C24	1.388 (2)
C7—C12	1.3825 (19)	C23—H23	0.9300
C7—C8	1.394 (2)	C17—C16	1.383 (3)
C7—C4	1.4908 (18)	C17—H17	0.9300
C20—C21	1.4854 (19)	C8—H8	0.9300
C20—C19	1.4987 (19)	C26—H26	0.9300
C21—C26	1.3897 (19)	C24—C27	1.507 (2)
C21—C22	1.391 (2)	C12—H12	0.9300
C10—C11	1.380 (2)	C16—H16	0.9300
C10—C9	1.3878 (19)	C5—C6	1.381 (2)
C19—C18	1.3929 (19)	C5—H5	0.9300
C4—C3	1.376 (2)	C3—C2	1.387 (2)
C4—C5	1.378 (2)	C3—H3	0.9300
C18—C17	1.377 (2)	C1—C6	1.356 (3)
C18—H18	0.9300	C1—C2	1.363 (3)
C11—C12	1.380 (2)	C1—H1	0.9300
C11—H11	0.9300	C2—H2	0.9300
C9—C8	1.382 (2)	C27—H27A	0.9600
C9—H9	0.9300	C27—H27B	0.9600
C15—C16	1.380 (2)	C27—H27C	0.9600
C15—H15	0.9300	C6—H6	0.9300
O1—C13—C10	122.55 (12)	C22—C23—C24	121.14 (15)
O1—C13—C14	120.89 (12)	C22—C23—H23	119.4
C10—C13—C14	116.52 (11)	C24—C23—H23	119.4
C15—C14—C19	119.29 (12)	C18—C17—C16	120.25 (14)
C15—C14—C13	119.20 (12)	C18—C17—H17	119.9
C19—C14—C13	121.41 (11)	C16—C17—H17	119.9
C12—C7—C8	116.82 (12)	C9—C8—C7	121.77 (13)
C12—C7—C4	120.98 (12)	C9—C8—H8	119.1
C8—C7—C4	122.19 (12)	C7—C8—H8	119.1
O2—C20—C21	121.61 (13)	C25—C26—C21	120.51 (14)
O2—C20—C19	119.99 (12)	C25—C26—H26	119.7
C21—C20—C19	118.39 (12)	C21—C26—H26	119.7
C26—C21—C22	118.29 (13)	C25—C24—C23	117.80 (14)
C26—C21—C20	119.21 (13)	C25—C24—C27	120.31 (16)
C22—C21—C20	122.44 (12)	C23—C24—C27	121.89 (16)
C11—C10—C9	118.26 (12)	C11—C12—C7	121.81 (13)
C11—C10—C13	120.85 (12)	C11—C12—H12	119.1
C9—C10—C13	120.87 (12)	C7—C12—H12	119.1
C18—C19—C14	119.20 (13)	C15—C16—C17	119.75 (14)
C18—C19—C20	120.14 (12)	C15—C16—H16	120.1
C14—C19—C20	120.42 (11)	C17—C16—H16	120.1
C3—C4—C5	116.35 (14)	C4—C5—C6	121.87 (16)
C3—C4—C7	122.13 (13)	C4—C5—H5	119.1
C5—C4—C7	121.51 (13)	C6—C5—H5	119.1
C17—C18—C19	120.63 (15)	C4—C3—C2	121.48 (16)
C17—C18—H18	119.7	C4—C3—H3	119.3
C19—C18—H18	119.7	C2—C3—H3	119.3
C12—C11—C10	120.89 (13)	C6—C1—C2	118.16 (15)
C12—C11—H11	119.6	C6—C1—H1	120.9
C10—C11—H11	119.6	C2—C1—H1	120.9
C8—C9—C10	120.36 (13)	C1—C2—C3	121.03 (17)
C8—C9—H9	119.8	C1—C2—H2	119.5
C10—C9—H9	119.8	C3—C2—H2	119.5
C16—C15—C14	120.81 (14)	C24—C27—H27A	109.5
C16—C15—H15	119.6	C24—C27—H27B	109.5
C14—C15—H15	119.6	H27A—C27—H27B	109.5
C26—C25—C24	121.53 (14)	C24—C27—H27C	109.5
C26—C25—H25	119.2	H27A—C27—H27C	109.5
C24—C25—H25	119.2	H27B—C27—H27C	109.5
C23—C22—C21	120.71 (14)	C1—C6—C5	121.10 (17)
C23—C22—H22	119.6	C1—C6—H6	119.4
C21—C22—H22	119.6	C5—C6—H6	119.4
O1—C13—C14—C15	120.10 (15)	C19—C14—C15—C16	−0.9 (2)
C10—C13—C14—C15	−57.39 (16)	C13—C14—C15—C16	−177.50 (13)
O1—C13—C14—C19	−56.44 (18)	C26—C21—C22—C23	0.0 (2)
C10—C13—C14—C19	126.07 (13)	C20—C21—C22—C23	−177.29 (14)
O2—C20—C21—C26	−22.7 (2)	C21—C22—C23—C24	−1.1 (2)
C19—C20—C21—C26	156.20 (13)	C19—C18—C17—C16	−0.9 (3)
O2—C20—C21—C22	154.55 (15)	C10—C9—C8—C7	−1.1 (3)
C19—C20—C21—C22	−26.53 (19)	C12—C7—C8—C9	−1.5 (2)
O1—C13—C10—C11	155.07 (15)	C4—C7—C8—C9	177.69 (15)
C14—C13—C10—C11	−27.48 (19)	C24—C25—C26—C21	−1.8 (2)
O1—C13—C10—C9	−23.5 (2)	C22—C21—C26—C25	1.4 (2)
C14—C13—C10—C9	153.91 (13)	C20—C21—C26—C25	178.82 (13)
C15—C14—C19—C18	2.3 (2)	C26—C25—C24—C23	0.7 (2)
C13—C14—C19—C18	178.87 (13)	C26—C25—C24—C27	−179.65 (16)
C15—C14—C19—C20	176.73 (12)	C22—C23—C24—C25	0.8 (2)
C13—C14—C19—C20	−6.7 (2)	C22—C23—C24—C27	−178.89 (15)
O2—C20—C19—C18	129.29 (16)	C10—C11—C12—C7	−1.1 (3)
C21—C20—C19—C18	−49.65 (19)	C8—C7—C12—C11	2.6 (3)
O2—C20—C19—C14	−45.1 (2)	C4—C7—C12—C11	−176.60 (15)
C21—C20—C19—C14	136.01 (13)	C14—C15—C16—C17	−1.5 (2)
C12—C7—C4—C3	176.57 (17)	C18—C17—C16—C15	2.4 (3)
C8—C7—C4—C3	−2.6 (2)	C3—C4—C5—C6	0.3 (3)
C12—C7—C4—C5	−2.4 (2)	C7—C4—C5—C6	179.32 (18)
C8—C7—C4—C5	178.45 (17)	C5—C4—C3—C2	−0.8 (3)
C14—C19—C18—C17	−1.5 (2)	C7—C4—C3—C2	−179.81 (18)
C20—C19—C18—C17	−175.88 (15)	C6—C1—C2—C3	0.7 (3)
C9—C10—C11—C12	−1.6 (2)	C4—C3—C2—C1	0.3 (4)
C13—C10—C11—C12	179.78 (15)	C2—C1—C6—C5	−1.2 (3)
C11—C10—C9—C8	2.6 (2)	C4—C5—C6—C1	0.7 (4)
C13—C10—C9—C8	−178.71 (14)

D—H···A	D—H	H···A	D···A	D—H···A
C16—H16···01i	0.93	2.57	3.4196 (18)	152

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C16—H16⋯01i	0.93	2.57	3.4196 (18)	152

Symmetry code: (i) .