meso-2,2'-Di­phenyl-3,3',4,4'-tetra­hydro-2,2'-bi­furan-5,5'(2H,2'H)-dione

The crystal structure of the title compound, C₂₀H₁₈O₄, contains a crystallographic inversion center. The C-C bond linking the two halves of the mol­ecule is slightly elongated at 1.577 (3) Å.

Computing details

Data collection: SMART (Bruker, 1997); cell refinement: SMART; data reduction: SMART; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); software used to prepare material for publication: SHELXL97.

meso-2,2'-Diphenyl-3,3',4,4'-tetrahydro-2,2'-bifuran-5,5'(2H,2'H)-dione

Crystal data

C20H18O4	F(000) = 340
Mr = 322.34	Dx = 1.333 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 9.4950 (11) Å	Cell parameters from 8662 reflections
b = 8.4241 (10) Å	θ = 5.6–28.3°
c = 10.0938 (12) Å	µ = 0.09 mm^−1
β = 95.876 (2)°	T = 296 K
V = 803.13 (16) Å^3	Cleaved_rectangle, colorless
Z = 2	0.64 × 0.46 × 0.24 mm

Data collection

Bruker SMART CCD 1K area-detector diffractometer	1977 independent reflections
Radiation source: fine-focus sealed tube	1458 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.040
ω scans	θmax = 28.3°, θmin = 5.6°
Absorption correction: empirical (using intensity measurements) (SADABS; Sheldrick 1996)	h = −12→12
Tmin = 0.943, Tmax = 0.978	k = −11→11
8662 measured reflections	l = −13→13

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.144	H-atom parameters constrained
S = 1.01	w = 1/[σ^2(Fo^2) + (0.0923P)^2 + 0.0603P] where P = (Fo^2 + 2Fc^2)/3
1977 reflections	(Δ/σ)max = 0.003
117 parameters	Δρmax = 0.31 e Å^−3
0 restraints	Δρmin = −0.21 e Å^−3

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
O1	0.42506 (10)	0.20034 (11)	0.48129 (10)	0.0407 (3)
O2	0.21582 (13)	0.31815 (15)	0.44174 (14)	0.0650 (4)
C1	0.48913 (13)	0.06504 (15)	0.55417 (13)	0.0345 (3)
C2	0.38075 (14)	0.01501 (19)	0.65050 (14)	0.0433 (4)
H2A	0.37118 (19)	−0.1007 (16)	0.65288 (15)	0.0605 (18)*
H2B	0.4093 (4)	0.0535 (5)	0.7408 (13)	0.0605 (18)*
C3	0.24314 (16)	0.0921 (2)	0.59360 (17)	0.0518 (4)
H3A	0.1813 (9)	0.0152 (11)	0.5477 (6)	0.0605 (18)*
H3B	0.1954 (7)	0.1397 (7)	0.6631 (10)	0.0605 (18)*
C4	0.28577 (15)	0.21559 (18)	0.49914 (16)	0.0455 (4)
C5	0.62953 (14)	0.11815 (15)	0.62579 (13)	0.0365 (3)
C6	0.69373 (16)	0.02845 (19)	0.73146 (14)	0.0444 (4)
H6	0.6449 (10)	−0.0666 (19)	0.7623 (6)	0.0605 (18)*
C7	0.82505 (17)	0.0712 (2)	0.79351 (16)	0.0524 (4)
H7	0.8686 (9)	0.0078 (14)	0.8648 (15)	0.0605 (18)*
C8	0.89365 (17)	0.2047 (2)	0.75318 (18)	0.0550 (4)
H8	0.9859 (18)	0.2343 (6)	0.7970 (9)	0.0605 (18)*
C9	0.83004 (16)	0.2958 (2)	0.64999 (18)	0.0534 (4)
H9	0.8791 (11)	0.393 (2)	0.6207 (7)	0.0605 (18)*
C10	0.69853 (15)	0.25390 (18)	0.58666 (16)	0.0438 (4)
H10	0.6557 (9)	0.3175 (14)	0.5169 (15)	0.0605 (18)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0416 (5)	0.0350 (5)	0.0448 (6)	0.0065 (4)	0.0009 (4)	0.0058 (4)
O2	0.0591 (7)	0.0560 (7)	0.0767 (9)	0.0224 (6)	−0.0091 (6)	−0.0005 (6)
C1	0.0359 (6)	0.0334 (6)	0.0340 (6)	0.0042 (5)	0.0031 (5)	0.0054 (5)
C2	0.0438 (8)	0.0512 (8)	0.0363 (7)	0.0014 (6)	0.0108 (6)	0.0025 (6)
C3	0.0404 (8)	0.0613 (10)	0.0551 (9)	0.0050 (6)	0.0124 (6)	−0.0054 (8)
C4	0.0416 (7)	0.0438 (8)	0.0495 (9)	0.0091 (6)	−0.0033 (6)	−0.0092 (6)
C5	0.0382 (7)	0.0368 (7)	0.0349 (7)	0.0033 (5)	0.0050 (5)	−0.0025 (5)
C6	0.0493 (8)	0.0456 (8)	0.0378 (7)	0.0047 (6)	0.0012 (6)	0.0022 (6)
C7	0.0497 (9)	0.0636 (10)	0.0419 (8)	0.0126 (7)	−0.0043 (6)	−0.0015 (7)
C8	0.0397 (8)	0.0681 (11)	0.0558 (10)	0.0024 (7)	−0.0019 (7)	−0.0139 (8)
C9	0.0447 (8)	0.0540 (9)	0.0618 (10)	−0.0070 (7)	0.0066 (7)	−0.0062 (7)
C10	0.0432 (7)	0.0424 (8)	0.0456 (8)	0.0003 (6)	0.0043 (6)	0.0017 (6)

Geometric parameters (Å, º)

O1—C4	1.3590 (17)	C5—C10	1.395 (2)
O1—C1	1.4556 (15)	C5—C6	1.3954 (19)
O2—C4	1.2019 (18)	C6—C7	1.384 (2)
C1—C5	1.5174 (18)	C6—H6	0.9916
C1—C2	1.5450 (19)	C7—C8	1.382 (3)
C1—C1^i	1.577 (3)	C7—H7	0.9556
C2—C3	1.518 (2)	C8—C9	1.382 (2)
C2—H2A	0.9792	C8—H8	0.9727
C2—H2B	0.9792	C9—C10	1.389 (2)
C3—C4	1.495 (2)	C9—H9	0.9992
C3—H3A	0.9611	C10—H10	0.9438
C3—H3B	0.9611
C4—O1—C1	111.66 (11)	O2—C4—C3	129.45 (15)
O1—C1—C5	108.14 (10)	O1—C4—C3	110.46 (12)
O1—C1—C2	105.12 (10)	C10—C5—C6	118.64 (13)
C5—C1—C2	112.95 (11)	C10—C5—C1	121.47 (12)
O1—C1—C1^i	105.74 (12)	C6—C5—C1	119.88 (12)
C5—C1—C1^i	111.37 (12)	C7—C6—C5	120.51 (15)
C2—C1—C1^i	112.95 (14)	C7—C6—H6	119.7
C3—C2—C1	104.37 (12)	C5—C6—H6	119.7
C3—C2—H2A	110.9	C8—C7—C6	120.55 (15)
C1—C2—H2A	110.9	C8—C7—H7	119.7
C3—C2—H2B	110.9	C6—C7—H7	119.7
C1—C2—H2B	110.9	C7—C8—C9	119.43 (15)
H2A—C2—H2B	108.9	C7—C8—H8	120.3
C4—C3—C2	105.08 (12)	C9—C8—H8	120.3
C4—C3—H3A	110.7	C8—C9—C10	120.57 (16)
C2—C3—H3A	110.7	C8—C9—H9	119.7
C4—C3—H3B	110.7	C10—C9—H9	119.7
C2—C3—H3B	110.7	C9—C10—C5	120.29 (15)
H3A—C3—H3B	108.8	C9—C10—H10	119.9
O2—C4—O1	120.09 (15)	C5—C10—H10	119.9
C4—O1—C1—C5	−134.00 (11)	C1^i—C1—C5—C10	96.12 (16)
C4—O1—C1—C2	−13.10 (14)	O1—C1—C5—C6	161.76 (12)
C4—O1—C1—C1^i	106.62 (14)	C2—C1—C5—C6	45.86 (16)
O1—C1—C2—C3	17.93 (15)	C1^i—C1—C5—C6	−82.48 (17)
C5—C1—C2—C3	135.61 (12)	C10—C5—C6—C7	−1.8 (2)
C1^i—C1—C2—C3	−96.88 (15)	C1—C5—C6—C7	176.85 (13)
C1—C2—C3—C4	−16.42 (16)	C5—C6—C7—C8	1.0 (2)
C1—O1—C4—O2	−177.26 (13)	C6—C7—C8—C9	0.0 (2)
C1—O1—C4—C3	2.55 (15)	C7—C8—C9—C10	−0.2 (2)
C2—C3—C4—O2	−170.91 (16)	C8—C9—C10—C5	−0.6 (2)
C2—C3—C4—O1	9.31 (16)	C6—C5—C10—C9	1.6 (2)
O1—C1—C5—C10	−19.65 (17)	C1—C5—C10—C9	−177.04 (13)
C2—C1—C5—C10	−135.55 (14)

Symmetry code: (i) −x+1, −y, −z+1.