Redermination of 9,9'-bianthracene-10,10'(9H,9'H)-dione.

The crystal structure of the title compound, C(28)H(18)O(2), was originally determined by Ehrenberg [(1967 ▶). Acta Cryst. 22, 482-487] using intensity data obtained from Weissenberg photographs. The current determination provides a crystal and mol-ecular structure with a significantly higher precision and presents standard uncertainties on geometric parameters which are not available from the original work. The mol-ecule lies on a crystallographic twofold rotation axis which bis-ects the C-C bond [1.603 (3) Å] which joins the two anthracen-9(10H)-one units.

Related literature

For general background, see: Li et al. (2002 ▶); Shi et al. (2004 ▶); Müller et al. (1996 ▶, 1998 ▶, 2001 ▶); Prinz, Burgemeister & Wiegrebe (1996 ▶); Prinz, Wiegrebe & Müller (1996 ▶). For related structures, see: Ehrenberg (1967 ▶).

Experimental

Crystal data

C28H18O2

M = 386.42

Monoclinic,

a = 22.295 (4) Å

b = 7.7297 (12) Å

c = 13.643 (2) Å

β = 126.768 (2)°

V = 1883.4 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 273 (2) K

0.22 × 0.18 × 0.15 mm

Data collection

Bruker SMART CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.982, T max = 0.987

4785 measured reflections

1669 independent reflections

1172 reflections with I > 2σ(I)

R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.105

S = 1.03

1669 reflections

136 parameters

H-atom parameters constrained

Δρmax = 0.12 e Å−3

Δρmin = −0.17 e Å−3

Data collection: SMART (Bruker, 2003 ▶); cell refinement: SAINT (Bruker, 2003 ▶); data reduction: SAINT; 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.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808028833/lh2689sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808028833/lh2689Isup2.hkl

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

C28H18O2	F(000) = 808
Mr = 386.42	Dx = 1.363 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 1069 reflections
a = 22.295 (4) Å	θ = 2.9–24.7°
b = 7.7297 (12) Å	µ = 0.09 mm−1
c = 13.643 (2) Å	T = 273 K
β = 126.768 (2)°	Block, yellow
V = 1883.4 (5) Å3	0.22 × 0.18 × 0.15 mm
Z = 4

Bruker SMART CCD diffractometer	1669 independent reflections
Radiation source: fine-focus sealed tube	1172 reflections with I > 2σ(I)
graphite	Rint = 0.025
φ and ω scans	θmax = 25.1°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −20→26
Tmin = 0.982, Tmax = 0.987	k = −9→9
4785 measured reflections	l = −16→8

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.106	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0478P)2 + 0.4019P] where P = (Fo2 + 2Fc2)/3
1669 reflections	(Δ/σ)max = 0.001
136 parameters	Δρmax = 0.12 e Å−3
0 restraints	Δρmin = −0.17 e Å−3

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	0.86707 (8)	−0.25682 (16)	0.29866 (15)	0.0855 (5)
C1	0.90675 (10)	−0.1382 (2)	0.30813 (16)	0.0503 (4)
C2	0.98793 (9)	−0.16248 (19)	0.37296 (14)	0.0423 (4)
C3	1.02019 (10)	−0.3196 (2)	0.43139 (15)	0.0546 (5)
H3	0.9900	−0.4083	0.4254	0.066*
C4	1.09595 (11)	−0.3451 (2)	0.49762 (16)	0.0616 (5)
H4	1.1169	−0.4513	0.5346	0.074*
C5	1.14056 (10)	−0.2121 (2)	0.50886 (15)	0.0572 (5)
H5	1.1921	−0.2277	0.5553	0.069*
C6	1.10969 (8)	−0.0560 (2)	0.45207 (13)	0.0457 (4)
H6	1.1408	0.0332	0.4616	0.055*
C7	1.03286 (8)	−0.02957 (19)	0.38070 (13)	0.0379 (4)
C8	0.99831 (8)	0.13334 (18)	0.30704 (13)	0.0370 (4)
H8	1.0288	0.2306	0.3599	0.044*
C9	0.91944 (8)	0.16565 (19)	0.26300 (13)	0.0393 (4)
C10	0.88717 (9)	0.3276 (2)	0.21705 (15)	0.0491 (4)
H10	0.9158	0.4170	0.2191	0.059*
C11	0.81329 (10)	0.3570 (2)	0.16860 (16)	0.0591 (5)
H11	0.7926	0.4660	0.1382	0.071*
C12	0.76987 (10)	0.2268 (3)	0.16480 (16)	0.0589 (5)
H12	0.7199	0.2471	0.1314	0.071*
C13	0.80076 (9)	0.0673 (2)	0.21051 (15)	0.0535 (5)
H13	0.7716	−0.0207	0.2086	0.064*
C14	0.87527 (8)	0.0352 (2)	0.25983 (14)	0.0426 (4)

	U11	U22	U33	U12	U13	U23
O1	0.0740 (10)	0.0554 (8)	0.1455 (14)	−0.0116 (7)	0.0756 (10)	0.0060 (8)
C1	0.0571 (11)	0.0449 (10)	0.0648 (11)	−0.0082 (8)	0.0450 (9)	−0.0049 (8)
C2	0.0527 (10)	0.0383 (9)	0.0436 (9)	−0.0017 (7)	0.0331 (8)	−0.0012 (7)
C3	0.0705 (13)	0.0430 (10)	0.0553 (11)	−0.0008 (9)	0.0403 (10)	0.0061 (8)
C4	0.0735 (14)	0.0512 (11)	0.0535 (11)	0.0147 (10)	0.0344 (10)	0.0138 (9)
C5	0.0496 (11)	0.0651 (12)	0.0458 (10)	0.0120 (9)	0.0227 (8)	0.0111 (9)
C6	0.0446 (10)	0.0512 (10)	0.0392 (9)	0.0003 (8)	0.0240 (8)	0.0024 (8)
C7	0.0447 (9)	0.0388 (9)	0.0327 (8)	0.0000 (7)	0.0245 (7)	−0.0022 (7)
C8	0.0394 (9)	0.0327 (8)	0.0406 (9)	−0.0041 (6)	0.0247 (7)	−0.0050 (7)
C9	0.0427 (9)	0.0384 (8)	0.0414 (9)	−0.0003 (7)	0.0276 (7)	−0.0074 (7)
C10	0.0502 (11)	0.0421 (9)	0.0571 (11)	0.0027 (8)	0.0333 (9)	−0.0037 (8)
C11	0.0568 (12)	0.0566 (11)	0.0606 (12)	0.0179 (9)	0.0333 (9)	0.0026 (9)
C12	0.0414 (10)	0.0781 (14)	0.0570 (11)	0.0074 (9)	0.0293 (9)	−0.0030 (10)
C13	0.0464 (10)	0.0645 (12)	0.0558 (11)	−0.0060 (9)	0.0339 (9)	−0.0081 (9)
C14	0.0429 (9)	0.0472 (9)	0.0451 (9)	−0.0033 (7)	0.0303 (8)	−0.0070 (7)

O1—C1	1.2260 (18)	C8—C9	1.500 (2)
C1—C14	1.473 (2)	C8—C8i	1.603 (3)
C1—C2	1.475 (2)	C8—H8	0.9800
C2—C3	1.393 (2)	C9—C10	1.392 (2)
C2—C7	1.394 (2)	C9—C14	1.392 (2)
C3—C4	1.372 (2)	C10—C11	1.378 (2)
C3—H3	0.9300	C10—H10	0.9300
C4—C5	1.374 (2)	C11—C12	1.376 (3)
C4—H4	0.9300	C11—H11	0.9300
C5—C6	1.375 (2)	C12—C13	1.367 (2)
C5—H5	0.9300	C12—H12	0.9300
C6—C7	1.388 (2)	C13—C14	1.391 (2)
C6—H6	0.9300	C13—H13	0.9300
C7—C8	1.504 (2)
O1—C1—C14	120.85 (16)	C7—C8—C8i	110.23 (10)
O1—C1—C2	121.12 (16)	C9—C8—H8	107.4
C14—C1—C2	117.97 (14)	C7—C8—H8	107.4
C3—C2—C7	119.84 (16)	C8i—C8—H8	107.4
C3—C2—C1	118.80 (15)	C10—C9—C14	118.18 (15)
C7—C2—C1	121.31 (14)	C10—C9—C8	119.74 (14)
C4—C3—C2	120.84 (17)	C14—C9—C8	121.98 (13)
C4—C3—H3	119.6	C11—C10—C9	120.78 (16)
C2—C3—H3	119.6	C11—C10—H10	119.6
C3—C4—C5	119.33 (17)	C9—C10—H10	119.6
C3—C4—H4	120.3	C12—C11—C10	120.62 (17)
C5—C4—H4	120.3	C12—C11—H11	119.7
C4—C5—C6	120.59 (17)	C10—C11—H11	119.7
C4—C5—H5	119.7	C13—C12—C11	119.45 (17)
C6—C5—H5	119.7	C13—C12—H12	120.3
C5—C6—C7	121.03 (16)	C11—C12—H12	120.3
C5—C6—H6	119.5	C12—C13—C14	120.73 (17)
C7—C6—H6	119.5	C12—C13—H13	119.6
C6—C7—C2	118.28 (14)	C14—C13—H13	119.6
C6—C7—C8	121.01 (14)	C13—C14—C9	120.23 (15)
C2—C7—C8	120.59 (14)	C13—C14—C1	119.33 (15)
C9—C8—C7	114.57 (13)	C9—C14—C1	120.43 (14)
C9—C8—C8i	109.65 (14)
O1—C1—C2—C3	−4.6 (2)	C7—C8—C9—C10	166.38 (13)
C14—C1—C2—C3	172.72 (15)	C8i—C8—C9—C10	−69.07 (14)
O1—C1—C2—C7	178.00 (16)	C7—C8—C9—C14	−17.4 (2)
C14—C1—C2—C7	−4.7 (2)	C8i—C8—C9—C14	107.14 (13)
C7—C2—C3—C4	0.6 (2)	C14—C9—C10—C11	−0.7 (2)
C1—C2—C3—C4	−176.90 (15)	C8—C9—C10—C11	175.66 (14)
C2—C3—C4—C5	1.7 (3)	C9—C10—C11—C12	0.1 (3)
C3—C4—C5—C6	−1.5 (3)	C10—C11—C12—C13	0.5 (3)
C4—C5—C6—C7	−1.0 (3)	C11—C12—C13—C14	−0.5 (3)
C5—C6—C7—C2	3.2 (2)	C12—C13—C14—C9	−0.1 (2)
C5—C6—C7—C8	−172.91 (15)	C12—C13—C14—C1	−179.91 (16)
C3—C2—C7—C6	−3.0 (2)	C10—C9—C14—C13	0.7 (2)
C1—C2—C7—C6	174.42 (14)	C8—C9—C14—C13	−175.56 (13)
C3—C2—C7—C8	173.14 (14)	C10—C9—C14—C1	−179.51 (14)
C1—C2—C7—C8	−9.5 (2)	C8—C9—C14—C1	4.2 (2)
C6—C7—C8—C9	−164.09 (13)	O1—C1—C14—C13	4.5 (3)
C2—C7—C8—C9	19.91 (19)	C2—C1—C14—C13	−172.84 (14)
C6—C7—C8—C8i	71.68 (18)	O1—C1—C14—C9	−175.31 (16)
C2—C7—C8—C8i	−104.32 (17)	C2—C1—C14—C9	7.4 (2)