(Biphenyl-4-yl)(phen-yl)methanone.

In the title compound, C(19)H(14)O, the dihedral angle between the two aromatic rings of the biphenyl residue is 8.0 (3)° and the dihedral angle between the two rings connected by the carbonyl C atom is 51.74 (18)°. There are no short C-H⋯O contacts in the crystal structure.

Related literature

For applications of the title compound, see: Kucybala & Wrzyszczynski (2002 ▶); van der Velden et al. (1980 ▶).

Experimental

Crystal data

C19H14O

M = 258.30

Orthorhombic,

a = 6.1445 (4) Å

b = 7.4298 (7) Å

c = 29.014 (2) Å

V = 1324.56 (18) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 173 K

0.32 × 0.29 × 0.12 mm

Data collection

Stoe IPDS II two-circle diffractometer

6073 measured reflections

1265 independent reflections

1193 reflections with I > 2σ(I)

R int = 0.071

Refinement

R[F 2 > 2σ(F 2)] = 0.077

wR(F 2) = 0.182

S = 1.13

1265 reflections

182 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.38 e Å−3

Δρmin = −0.41 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 (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810010676/hb5370sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810010676/hb5370Isup2.hkl

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

C19H14O	F(000) = 544
Mr = 258.30	Dx = 1.295 Mg m−3
Orthorhombic, Pca21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2ac	Cell parameters from 4666 reflections
a = 6.1445 (4) Å	θ = 2.8–25.9°
b = 7.4298 (7) Å	µ = 0.08 mm−1
c = 29.014 (2) Å	T = 173 K
V = 1324.56 (18) Å3	Plate, colourless
Z = 4	0.32 × 0.29 × 0.12 mm

Stoe IPDS II two-circle diffractometer	1193 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.071
graphite	θmax = 25.6°, θmin = 2.7°
ω scans	h = −6→7
6073 measured reflections	k = −9→8
1265 independent reflections	l = −35→35

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)] = 0.077	H-atom parameters constrained
wR(F2) = 0.182	w = 1/[σ2(Fo2) + (0.0331P)2 + 3.7315P] where P = (Fo2 + 2Fc2)/3
S = 1.13	(Δ/σ)max < 0.001
1265 reflections	Δρmax = 0.38 e Å−3
182 parameters	Δρmin = −0.41 e Å−3
1 restraint	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.032 (5)

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 > 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	0.9334 (9)	0.2473 (12)	0.5985 (3)	0.0345 (14)
O1	1.1328 (7)	0.2424 (10)	0.5980 (2)	0.0489 (14)
C11	0.8158 (12)	0.2442 (9)	0.6443 (2)	0.0329 (18)
C12	0.6194 (12)	0.3247 (12)	0.6502 (3)	0.045 (2)
H12	0.5463	0.3761	0.6245	0.055*
C13	0.5235 (12)	0.3323 (11)	0.6943 (2)	0.0418 (19)
H13	0.3865	0.3890	0.6988	0.050*
C14	0.6325 (14)	0.2562 (12)	0.7305 (3)	0.050 (2)
H14	0.5711	0.2643	0.7605	0.060*
C15	0.8288 (12)	0.1680 (9)	0.7250 (2)	0.0351 (17)
H15	0.8991	0.1124	0.7505	0.042*
C16	0.9205 (12)	0.1628 (11)	0.6813 (2)	0.0363 (18)
H16	1.0557	0.1033	0.6767	0.044*
C21	0.8136 (11)	0.2548 (7)	0.5540 (2)	0.0265 (15)
C22	0.6040 (10)	0.1827 (8)	0.5471 (2)	0.0243 (14)
H22	0.5254	0.1355	0.5726	0.029*
C23	0.5128 (11)	0.1800 (10)	0.5041 (2)	0.0316 (16)
H23	0.3734	0.1266	0.5003	0.038*
C24	0.6188 (11)	0.2540 (7)	0.4649 (2)	0.0222 (14)
C25	0.8263 (11)	0.3235 (10)	0.4727 (2)	0.0344 (17)
H25	0.9029	0.3739	0.4474	0.041*
C26	0.9260 (11)	0.3227 (11)	0.5153 (2)	0.0341 (17)
H26	1.0698	0.3678	0.5186	0.041*
C31	0.5192 (10)	0.2543 (8)	0.4186 (2)	0.0285 (14)
C32	0.3245 (11)	0.1634 (9)	0.4098 (2)	0.0330 (16)
H32	0.2518	0.1041	0.4344	0.040*
C33	0.2347 (12)	0.1577 (9)	0.3659 (3)	0.0370 (16)
H33	0.1035	0.0931	0.3608	0.044*
C34	0.3348 (12)	0.2456 (10)	0.3295 (2)	0.0380 (17)
H34	0.2726	0.2437	0.2995	0.046*
C35	0.5263 (12)	0.3357 (11)	0.3378 (2)	0.0415 (19)
H35	0.5977	0.3954	0.3131	0.050*
C36	0.6174 (11)	0.3412 (10)	0.3814 (2)	0.0360 (17)
H36	0.7492	0.4054	0.3861	0.043*

	U11	U22	U33	U12	U13	U23
C1	0.022 (3)	0.044 (4)	0.037 (3)	0.001 (3)	−0.001 (4)	−0.002 (3)
O1	0.023 (2)	0.086 (4)	0.037 (2)	−0.007 (3)	0.004 (3)	−0.007 (2)
C11	0.026 (4)	0.047 (5)	0.026 (4)	−0.006 (3)	0.004 (3)	−0.001 (3)
C12	0.026 (4)	0.077 (6)	0.033 (4)	−0.006 (4)	−0.006 (3)	0.003 (4)
C13	0.032 (4)	0.055 (5)	0.038 (4)	0.005 (4)	0.003 (3)	−0.006 (4)
C14	0.039 (5)	0.074 (7)	0.038 (5)	−0.003 (4)	0.005 (4)	−0.006 (4)
C15	0.041 (4)	0.031 (4)	0.033 (4)	−0.006 (3)	−0.002 (3)	−0.003 (3)
C16	0.025 (4)	0.049 (5)	0.034 (4)	0.000 (3)	−0.005 (3)	−0.009 (4)
C21	0.023 (3)	0.014 (3)	0.042 (4)	−0.003 (2)	0.010 (3)	−0.006 (3)
C22	0.025 (3)	0.017 (3)	0.031 (4)	−0.003 (3)	0.001 (3)	−0.002 (3)
C23	0.023 (3)	0.038 (4)	0.034 (4)	0.000 (3)	0.004 (3)	−0.004 (3)
C24	0.025 (3)	0.018 (3)	0.024 (3)	0.005 (2)	0.000 (3)	−0.003 (3)
C25	0.025 (4)	0.046 (4)	0.032 (4)	−0.008 (3)	0.011 (3)	0.001 (3)
C26	0.020 (3)	0.047 (5)	0.035 (4)	−0.002 (3)	0.001 (3)	0.004 (3)
C31	0.022 (3)	0.028 (3)	0.035 (4)	−0.003 (3)	0.001 (3)	−0.003 (3)
C32	0.036 (4)	0.028 (3)	0.034 (4)	−0.009 (3)	−0.001 (3)	0.002 (3)
C33	0.035 (3)	0.032 (4)	0.044 (4)	0.001 (3)	−0.003 (3)	−0.006 (3)
C34	0.038 (4)	0.048 (5)	0.028 (3)	0.010 (3)	−0.006 (3)	−0.002 (3)
C35	0.034 (4)	0.057 (5)	0.033 (4)	0.003 (4)	0.004 (3)	−0.001 (3)
C36	0.025 (3)	0.053 (4)	0.030 (3)	−0.006 (3)	0.000 (3)	−0.003 (3)

C1—O1	1.226 (7)	C23—C24	1.421 (9)
C1—C21	1.489 (10)	C23—H23	0.9500
C1—C11	1.512 (10)	C24—C25	1.393 (9)
C11—C12	1.357 (11)	C24—C31	1.476 (9)
C11—C16	1.391 (11)	C25—C26	1.380 (10)
C12—C13	1.412 (10)	C25—H25	0.9500
C12—H12	0.9500	C26—H26	0.9500
C13—C14	1.368 (11)	C31—C32	1.398 (9)
C13—H13	0.9500	C31—C36	1.395 (9)
C14—C15	1.382 (11)	C32—C33	1.388 (10)
C14—H14	0.9500	C32—H32	0.9500
C15—C16	1.388 (10)	C33—C34	1.387 (10)
C15—H15	0.9500	C33—H33	0.9500
C16—H16	0.9500	C34—C35	1.375 (10)
C21—C22	1.409 (9)	C34—H34	0.9500
C21—C26	1.410 (10)	C35—C36	1.385 (9)
C22—C23	1.368 (9)	C35—H35	0.9500
C22—H22	0.9500	C36—H36	0.9500
O1—C1—C21	119.0 (8)	C24—C23—H23	118.8
O1—C1—C11	119.3 (8)	C25—C24—C23	115.7 (6)
C21—C1—C11	121.8 (5)	C25—C24—C31	121.8 (6)
C12—C11—C16	120.4 (7)	C23—C24—C31	122.5 (6)
C12—C11—C1	121.9 (7)	C26—C25—C24	123.4 (6)
C16—C11—C1	117.6 (7)	C26—C25—H25	118.3
C11—C12—C13	120.2 (7)	C24—C25—H25	118.3
C11—C12—H12	119.9	C25—C26—C21	119.8 (6)
C13—C12—H12	119.9	C25—C26—H26	120.1
C14—C13—C12	118.4 (7)	C21—C26—H26	120.1
C14—C13—H13	120.8	C32—C31—C36	116.8 (6)
C12—C13—H13	120.8	C32—C31—C24	121.5 (6)
C13—C14—C15	122.3 (8)	C36—C31—C24	121.7 (5)
C13—C14—H14	118.8	C33—C32—C31	121.6 (6)
C15—C14—H14	118.8	C33—C32—H32	119.2
C14—C15—C16	118.2 (8)	C31—C32—H32	119.2
C14—C15—H15	120.9	C34—C33—C32	120.6 (7)
C16—C15—H15	120.9	C34—C33—H33	119.7
C15—C16—C11	120.4 (7)	C32—C33—H33	119.7
C15—C16—H16	119.8	C35—C34—C33	118.4 (7)
C11—C16—H16	119.8	C35—C34—H34	120.8
C22—C21—C26	118.1 (7)	C33—C34—H34	120.8
C22—C21—C1	124.1 (6)	C34—C35—C36	121.4 (7)
C26—C21—C1	117.5 (6)	C34—C35—H35	119.3
C23—C22—C21	120.6 (6)	C36—C35—H35	119.3
C23—C22—H22	119.7	C35—C36—C31	121.3 (6)
C21—C22—H22	119.7	C35—C36—H36	119.4
C22—C23—C24	122.4 (6)	C31—C36—H36	119.4
C22—C23—H23	118.8
O1—C1—C11—C12	150.5 (9)	C22—C23—C24—C25	2.5 (9)
C21—C1—C11—C12	−29.9 (12)	C22—C23—C24—C31	−178.9 (6)
O1—C1—C11—C16	−26.5 (13)	C23—C24—C25—C26	−0.2 (10)
C21—C1—C11—C16	153.1 (7)	C31—C24—C25—C26	−178.9 (7)
C16—C11—C12—C13	2.3 (12)	C24—C25—C26—C21	−2.3 (11)
C1—C11—C12—C13	−174.5 (8)	C22—C21—C26—C25	2.5 (10)
C11—C12—C13—C14	−0.4 (12)	C1—C21—C26—C25	176.5 (7)
C12—C13—C14—C15	−2.0 (13)	C25—C24—C31—C32	171.3 (6)
C13—C14—C15—C16	2.3 (12)	C23—C24—C31—C32	−7.3 (9)
C14—C15—C16—C11	−0.2 (11)	C25—C24—C31—C36	−7.0 (9)
C12—C11—C16—C15	−2.1 (11)	C23—C24—C31—C36	174.4 (6)
C1—C11—C16—C15	174.9 (7)	C36—C31—C32—C33	0.9 (9)
O1—C1—C21—C22	150.3 (8)	C24—C31—C32—C33	−177.5 (6)
C11—C1—C21—C22	−29.3 (11)	C31—C32—C33—C34	−1.1 (11)
O1—C1—C21—C26	−23.3 (12)	C32—C33—C34—C35	1.0 (11)
C11—C1—C21—C26	157.1 (7)	C33—C34—C35—C36	−0.7 (11)
C26—C21—C22—C23	−0.3 (9)	C34—C35—C36—C31	0.5 (12)
C1—C21—C22—C23	−173.9 (7)	C32—C31—C36—C35	−0.6 (10)
C21—C22—C23—C24	−2.2 (10)	C24—C31—C36—C35	177.8 (6)