Diphenyl-methyl benzoate.

In the title mol-ecule, C20H16O2, the dihedral angle between the phenyl rings of the diphenyl-methyl group is 68.3 (2)°. The benzoate group is essentially planar, with a maximum deviation of 0.017 (2) Å for the carbonyl O atom, and the two phenyl rings are twisted by 27.5 (4) and 85.6 (9)° from this plane. In the crystal, weak C-H⋯O hydrogen bonds link mol-ecules along [100].

Related literature

For related structures, see: Baidya et al. (2009a ▶,b ▶); Gowda et al. (2007 ▶, 2009 ▶). For standard bond lengths, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C20H16O2

M = 288.33

Monoclinic,

a = 5.75357 (19) Å

b = 16.0368 (5) Å

c = 8.3114 (3) Å

β = 95.340 (3)°

V = 763.55 (4) Å3

Z = 2

Cu Kα radiation

μ = 0.63 mm−1

T = 173 K

0.38 × 0.26 × 0.24 mm

Data collection

Agilent Xcalibur (Eos, Gemini) diffractometer

Absorption correction: multi-scan (CrysAlis PRO and CrysAlis RED; Agilent, 2012 ▶) T min = 0.912, T max = 1.000

4414 measured reflections

2659 independent reflections

2528 reflections with I > 2σ(I)

R int = 0.022

Refinement

R[F 2 > 2σ(F 2)] = 0.035

wR(F 2) = 0.094

S = 1.06

2659 reflections

200 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.21 e Å−3

Δρmin = −0.15 e Å−3

Absolute structure: Flack (1983 ▶) 1120 Friedel pairs

Flack parameter: 0.0 (2)

Data collection: CrysAlis PRO (Agilent, 2012 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis RED (Agilent, 2012 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812050064/lh5566sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812050064/lh5566Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536812050064/lh5566Isup3.cml

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

C20H16O2	F(000) = 304
Mr = 288.33	Dx = 1.254 Mg m−3
Monoclinic, P21	Cu Kα radiation, λ = 1.54184 Å
Hall symbol: P 2yb	Cell parameters from 2446 reflections
a = 5.75357 (19) Å	θ = 5.3–72.4°
b = 16.0368 (5) Å	µ = 0.63 mm−1
c = 8.3114 (3) Å	T = 173 K
β = 95.340 (3)°	Block, colorless
V = 763.55 (4) Å3	0.38 × 0.26 × 0.24 mm
Z = 2

Agilent Xcalibur (Eos, Gemini) diffractometer	2659 independent reflections
Radiation source: Enhance (Cu) X-ray Source	2528 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.022
Detector resolution: 16.0416 pixels mm-1	θmax = 72.5°, θmin = 5.4°
ω scans	h = −7→5
Absorption correction: multi-scan (CrysAlis PRO and CrysAlis RED; Agilent, 2012)	k = −17→19
Tmin = 0.912, Tmax = 1.000	l = −6→10
4414 measured reflections

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.035	w = 1/[σ2(Fo2) + (0.0518P)2 + 0.052P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.094	(Δ/σ)max < 0.001
S = 1.06	Δρmax = 0.21 e Å−3
2659 reflections	Δρmin = −0.15 e Å−3
200 parameters	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
1 restraint	Extinction coefficient: 0.0104 (11)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983) 1120 Friedel pairs
Secondary atom site location: difference Fourier map	Flack parameter: 0.0 (2)

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
O1	0.2173 (2)	0.33454 (8)	0.50213 (15)	0.0376 (3)
O2	−0.1042 (2)	0.31628 (10)	0.63104 (18)	0.0495 (4)
C1	0.1598 (3)	0.42599 (10)	0.7144 (2)	0.0312 (4)
C2	0.3646 (3)	0.46769 (11)	0.6891 (2)	0.0364 (4)
H2	0.4547	0.4498	0.6085	0.044*
C3	0.4349 (4)	0.53567 (12)	0.7833 (2)	0.0434 (4)
H3	0.5709	0.5640	0.7648	0.052*
C4	0.3036 (4)	0.56172 (13)	0.9049 (2)	0.0465 (5)
H4	0.3514	0.6074	0.9685	0.056*
C5	0.1008 (4)	0.51969 (13)	0.9320 (2)	0.0491 (5)
H5	0.0133	0.5370	1.0145	0.059*
C6	0.0279 (3)	0.45254 (12)	0.8375 (2)	0.0407 (4)
H6	−0.1092	0.4248	0.8556	0.049*
C7	0.0735 (3)	0.35370 (11)	0.6150 (2)	0.0329 (4)
C8	0.1615 (3)	0.26034 (11)	0.4044 (2)	0.0339 (4)
H8	−0.0074	0.2579	0.3758	0.041*
C9	0.2833 (3)	0.27104 (10)	0.2523 (2)	0.0350 (4)
C10	0.4936 (3)	0.31388 (13)	0.2513 (2)	0.0408 (4)
H10	0.5615	0.3381	0.3459	0.049*
C11	0.6021 (4)	0.32051 (14)	0.1099 (3)	0.0459 (5)
H11	0.7420	0.3495	0.1101	0.055*
C12	0.5040 (4)	0.28435 (12)	−0.0315 (2)	0.0452 (5)
H12	0.5776	0.2890	−0.1261	0.054*
C13	0.2964 (4)	0.24132 (14)	−0.0317 (2)	0.0459 (5)
H13	0.2304	0.2166	−0.1264	0.055*
C14	0.1859 (3)	0.23482 (12)	0.1092 (2)	0.0400 (4)
H14	0.0455	0.2060	0.1081	0.048*
C15	0.2380 (3)	0.18357 (11)	0.50053 (19)	0.0327 (4)
C16	0.4629 (3)	0.17795 (12)	0.5773 (2)	0.0381 (4)
H16	0.5683	0.2212	0.5672	0.046*
C17	0.5304 (4)	0.10861 (14)	0.6684 (2)	0.0456 (5)
H17	0.6804	0.1056	0.7204	0.055*
C18	0.3756 (4)	0.04356 (13)	0.6827 (2)	0.0494 (5)
H18	0.4206	−0.0028	0.7452	0.059*
C19	0.1538 (4)	0.04782 (13)	0.6037 (3)	0.0514 (5)
H19	0.0504	0.0038	0.6115	0.062*
C20	0.0851 (4)	0.11732 (13)	0.5130 (2)	0.0421 (4)
H20	−0.0644	0.1197	0.4601	0.051*

	U11	U22	U33	U12	U13	U23
O1	0.0385 (7)	0.0341 (7)	0.0422 (7)	−0.0057 (5)	0.0136 (5)	−0.0087 (5)
O2	0.0401 (7)	0.0565 (9)	0.0543 (8)	−0.0152 (6)	0.0172 (6)	−0.0205 (7)
C1	0.0333 (8)	0.0287 (8)	0.0316 (8)	0.0040 (6)	0.0032 (6)	0.0031 (6)
C2	0.0354 (9)	0.0348 (9)	0.0396 (9)	−0.0008 (7)	0.0058 (7)	0.0002 (7)
C3	0.0415 (10)	0.0386 (10)	0.0494 (11)	−0.0062 (8)	0.0002 (8)	0.0021 (9)
C4	0.0569 (12)	0.0358 (10)	0.0451 (10)	−0.0034 (9)	−0.0047 (9)	−0.0076 (8)
C5	0.0602 (13)	0.0475 (12)	0.0410 (11)	0.0031 (10)	0.0129 (9)	−0.0103 (9)
C6	0.0410 (10)	0.0402 (10)	0.0419 (10)	−0.0016 (8)	0.0082 (8)	−0.0030 (8)
C7	0.0318 (8)	0.0333 (9)	0.0340 (8)	0.0016 (7)	0.0047 (7)	−0.0001 (7)
C8	0.0327 (8)	0.0345 (9)	0.0349 (8)	−0.0039 (7)	0.0050 (7)	−0.0062 (7)
C9	0.0395 (9)	0.0303 (9)	0.0354 (8)	0.0045 (7)	0.0056 (7)	0.0010 (7)
C10	0.0428 (10)	0.0413 (10)	0.0393 (9)	−0.0018 (8)	0.0088 (8)	−0.0016 (8)
C11	0.0495 (11)	0.0415 (11)	0.0487 (10)	0.0004 (9)	0.0152 (8)	0.0058 (9)
C12	0.0589 (12)	0.0427 (11)	0.0363 (9)	0.0099 (9)	0.0172 (9)	0.0070 (8)
C13	0.0609 (12)	0.0443 (11)	0.0324 (9)	0.0086 (9)	0.0032 (8)	−0.0021 (8)
C14	0.0420 (9)	0.0379 (10)	0.0401 (9)	0.0039 (8)	0.0035 (8)	−0.0035 (8)
C15	0.0374 (9)	0.0340 (9)	0.0282 (8)	−0.0040 (7)	0.0108 (7)	−0.0075 (6)
C16	0.0391 (10)	0.0423 (10)	0.0338 (9)	−0.0060 (8)	0.0076 (7)	−0.0023 (7)
C17	0.0448 (11)	0.0580 (13)	0.0349 (9)	0.0062 (9)	0.0083 (8)	0.0008 (9)
C18	0.0722 (15)	0.0392 (11)	0.0382 (10)	0.0059 (10)	0.0123 (9)	0.0006 (8)
C19	0.0683 (14)	0.0364 (11)	0.0504 (11)	−0.0152 (10)	0.0108 (10)	−0.0032 (9)
C20	0.0421 (10)	0.0423 (10)	0.0427 (10)	−0.0100 (8)	0.0073 (8)	−0.0065 (8)

O1—C7	1.343 (2)	C10—C11	1.385 (3)
O1—C8	1.460 (2)	C10—H10	0.9300
O2—C7	1.203 (2)	C11—C12	1.383 (3)
C1—C2	1.388 (2)	C11—H11	0.9300
C1—C6	1.396 (2)	C12—C13	1.379 (3)
C1—C7	1.482 (2)	C12—H12	0.9300
C2—C3	1.381 (3)	C13—C14	1.387 (3)
C2—H2	0.9300	C13—H13	0.9300
C3—C4	1.382 (3)	C14—H14	0.9300
C3—H3	0.9300	C15—C20	1.390 (2)
C4—C5	1.384 (3)	C15—C16	1.392 (2)
C4—H4	0.9300	C16—C17	1.380 (3)
C5—C6	1.375 (3)	C16—H16	0.9300
C5—H5	0.9300	C17—C18	1.384 (3)
C6—H6	0.9300	C17—H17	0.9300
C8—C15	1.511 (3)	C18—C19	1.381 (3)
C8—C9	1.511 (2)	C18—H18	0.9300
C8—H8	0.9800	C19—C20	1.382 (3)
C9—C10	1.392 (3)	C19—H19	0.9300
C9—C14	1.394 (3)	C20—H20	0.9300
C7—O1—C8	117.21 (13)	C11—C10—H10	119.9
C2—C1—C6	119.42 (17)	C9—C10—H10	119.9
C2—C1—C7	122.53 (15)	C12—C11—C10	120.54 (19)
C6—C1—C7	118.05 (16)	C12—C11—H11	119.7
C3—C2—C1	120.18 (18)	C10—C11—H11	119.7
C3—C2—H2	119.9	C13—C12—C11	119.72 (17)
C1—C2—H2	119.9	C13—C12—H12	120.1
C2—C3—C4	120.15 (18)	C11—C12—H12	120.1
C2—C3—H3	119.9	C12—C13—C14	120.08 (18)
C4—C3—H3	119.9	C12—C13—H13	120.0
C3—C4—C5	119.89 (18)	C14—C13—H13	120.0
C3—C4—H4	120.1	C13—C14—C9	120.65 (18)
C5—C4—H4	120.1	C13—C14—H14	119.7
C6—C5—C4	120.37 (19)	C9—C14—H14	119.7
C6—C5—H5	119.8	C20—C15—C16	118.97 (17)
C4—C5—H5	119.8	C20—C15—C8	120.50 (16)
C5—C6—C1	119.98 (18)	C16—C15—C8	120.53 (16)
C5—C6—H6	120.0	C17—C16—C15	120.40 (18)
C1—C6—H6	120.0	C17—C16—H16	119.8
O2—C7—O1	123.26 (16)	C15—C16—H16	119.8
O2—C7—C1	124.91 (16)	C16—C17—C18	120.2 (2)
O1—C7—C1	111.83 (14)	C16—C17—H17	119.9
O1—C8—C15	109.39 (13)	C18—C17—H17	119.9
O1—C8—C9	106.13 (14)	C19—C18—C17	119.7 (2)
C15—C8—C9	113.59 (14)	C19—C18—H18	120.1
O1—C8—H8	109.2	C17—C18—H18	120.1
C15—C8—H8	109.2	C18—C19—C20	120.2 (2)
C9—C8—H8	109.2	C18—C19—H19	119.9
C10—C9—C14	118.75 (16)	C20—C19—H19	119.9
C10—C9—C8	122.17 (15)	C19—C20—C15	120.42 (19)
C14—C9—C8	119.06 (16)	C19—C20—H20	119.8
C11—C10—C9	120.26 (18)	C15—C20—H20	119.8
C6—C1—C2—C3	−1.1 (3)	C14—C9—C10—C11	0.4 (3)
C7—C1—C2—C3	178.80 (17)	C8—C9—C10—C11	178.47 (18)
C1—C2—C3—C4	1.0 (3)	C9—C10—C11—C12	−0.4 (3)
C2—C3—C4—C5	−0.2 (3)	C10—C11—C12—C13	0.0 (3)
C3—C4—C5—C6	−0.6 (3)	C11—C12—C13—C14	0.4 (3)
C4—C5—C6—C1	0.5 (3)	C12—C13—C14—C9	−0.4 (3)
C2—C1—C6—C5	0.3 (3)	C10—C9—C14—C13	0.0 (3)
C7—C1—C6—C5	−179.60 (17)	C8—C9—C14—C13	−178.14 (17)
C8—O1—C7—O2	−5.1 (3)	O1—C8—C15—C20	129.89 (16)
C8—O1—C7—C1	175.31 (13)	C9—C8—C15—C20	−111.75 (18)
C2—C1—C7—O2	−179.04 (19)	O1—C8—C15—C16	−50.40 (19)
C6—C1—C7—O2	0.8 (3)	C9—C8—C15—C16	68.0 (2)
C2—C1—C7—O1	0.5 (2)	C20—C15—C16—C17	−1.9 (3)
C6—C1—C7—O1	−179.61 (16)	C8—C15—C16—C17	178.38 (15)
C7—O1—C8—C15	−78.53 (17)	C15—C16—C17—C18	0.7 (3)
C7—O1—C8—C9	158.56 (14)	C16—C17—C18—C19	0.8 (3)
O1—C8—C9—C10	31.5 (2)	C17—C18—C19—C20	−1.1 (3)
C15—C8—C9—C10	−88.7 (2)	C18—C19—C20—C15	−0.1 (3)
O1—C8—C9—C14	−150.37 (15)	C16—C15—C20—C19	1.6 (3)
C15—C8—C9—C14	89.40 (19)	C8—C15—C20—C19	−178.71 (17)

D—H···A	D—H	H···A	D···A	D—H···A
C16—H16···O2i	0.93	2.44	3.334 (2)	160

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C16—H16⋯O2i	0.93	2.44	3.334 (2)	160

Symmetry code: (i) .