(3Z,3'Z)-3,3'-(Ethane-1,2-diyl-idene)-bis[isobenzofuran-1(3H)-one].

The title compound, C(18)H(10)O(4), has been isolated as an impurity in commercially available 6,11-dihydr-oxy-5,12-naphth-acenedione. The title compound exhibits yellow fluorescence in the solid state. The mol-ecule has crystallographic inversion symmetry and is planar, with an r.m.s. deviation of 0.031 (1) Å. The crystal structure is stabilized by C-H⋯O hydrogen bonds and π-π stacking inter-actions between 3-methyl-eneisobenzofuran-1(3H)-one units [inter-planar distance 3.43 (1) Å].

Related literature

For the crystallographic analysis and functionalization of 6,11-dihydr­oxy-5,12-naphthacenedione, see: Tomura et al. (2008 ▶); Ono et al. (2009 ▶). For the synthesis of the title compound, see: Ji et al. (2006 ▶).

Experimental

Crystal data

C18H10O4

M = 290.26

Triclinic,

a = 6.9030 (13) Å

b = 7.0374 (16) Å

c = 7.7792 (13) Å

α = 112.190 (5)°

β = 95.696 (2)°

γ = 107.239 (8)°

V = 324.53 (11) Å3

Z = 1

Mo Kα radiation

μ = 0.11 mm−1

T = 173 K

1.00 × 0.50 × 0.40 mm

Data collection

Rigaku/MSC Mercury CCD diffractometer

Absorption correction: none

2656 measured reflections

1661 independent reflections

1323 reflections with I > 2σ(I)

R int = 0.044

Refinement

R[F 2 > 2σ(F 2)] = 0.066

wR(F 2) = 0.176

S = 0.97

1661 reflections

100 parameters

H-atom parameters constrained

Δρmax = 0.35 e Å−3

Δρmin = −0.28 e Å−3

Data collection: CrystalClear (Rigaku/MSC, 2006 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SIR2004 (Burla et al., 2005 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶) and Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809030888/bt5025sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809030888/bt5025Isup2.hkl

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

C18H10O4	Z = 1
Mr = 290.26	F(000) = 150
Triclinic, P1	Dx = 1.485 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.9030 (13) Å	Cell parameters from 1131 reflections
b = 7.0374 (16) Å	θ = 4.8–30.8°
c = 7.7792 (13) Å	µ = 0.11 mm−1
α = 112.190 (5)°	T = 173 K
β = 95.696 (2)°	Prism, yellow
γ = 107.239 (8)°	1.00 × 0.50 × 0.40 mm
V = 324.53 (11) Å3

Rigaku/MSC Mercury CCD diffractometer	1323 reflections with I > 2σ(I)
Radiation source: Rotating Anode	Rint = 0.044
Graphite Monochromator	θmax = 30.8°, θmin = 3.7°
Detector resolution: 14.62 pixels mm-1	h = −9→9
φ and ω scans	k = −9→5
2656 measured reflections	l = −7→10
1661 independent reflections

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)] = 0.066	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.176	H-atom parameters constrained
S = 0.97	w = 1/[σ2(Fo2) + (0.1211P)2] where P = (Fo2 + 2Fc2)/3
1661 reflections	(Δ/σ)max < 0.001
100 parameters	Δρmax = 0.35 e Å−3
0 restraints	Δρmin = −0.28 e Å−3

Experimental. IR (KBr, cm-1): 1784, 1645, 1472, 1343, 1281, 1073, 974, 766, 689; 1H NMR (CDCl3, δ p.p.m.): 6.86 (s, 2H), 7.60 (t, J = 7.6 Hz, 2H), 7.77 (t, J = 7.6 Hz, 2H), 7.81 (d, J = 7.6 Hz, 2H), 7.96 (d, J = 7.6 Hz, 2H); MS (EI): m/z 290 (M+), 104; UV-vis (CH2Cl2, nm): 406, 383.

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
C1	0.7382 (2)	0.6230 (2)	0.8120 (2)	0.0242 (4)
C2	0.7695 (2)	0.5873 (2)	0.9849 (2)	0.0216 (4)
C3	0.8463 (2)	0.7402 (2)	1.1749 (2)	0.0285 (4)
H3	0.8898	0.8939	1.2100	0.034*
C4	0.8568 (2)	0.6597 (3)	1.3105 (2)	0.0320 (4)
H4	0.9049	0.7593	1.4421	0.038*
C5	0.7974 (2)	0.4324 (3)	1.2568 (2)	0.0310 (4)
H5	0.8079	0.3814	1.3531	0.037*
C6	0.7236 (2)	0.2804 (2)	1.0665 (2)	0.0267 (4)
H6	0.6859	0.1271	1.0308	0.032*
C7	0.7070 (2)	0.3616 (2)	0.9299 (2)	0.0204 (3)
C8	0.6284 (2)	0.2534 (2)	0.7233 (2)	0.0207 (3)
C9	0.5404 (2)	0.0392 (2)	0.6005 (2)	0.0223 (4)
H9	0.5313	−0.0668	0.6501	0.027*
O1	0.65059 (16)	0.41594 (15)	0.65779 (15)	0.0248 (3)
O2	0.77382 (19)	0.78743 (17)	0.78771 (18)	0.0364 (4)

	U11	U22	U33	U12	U13	U23
C1	0.0231 (7)	0.0198 (7)	0.0242 (8)	0.0061 (6)	0.0010 (6)	0.0061 (6)
C2	0.0187 (6)	0.0193 (7)	0.0207 (7)	0.0044 (5)	0.0025 (5)	0.0046 (5)
C3	0.0263 (8)	0.0231 (7)	0.0245 (8)	0.0056 (6)	0.0027 (6)	0.0016 (6)
C4	0.0296 (8)	0.0343 (9)	0.0180 (8)	0.0048 (7)	0.0024 (6)	0.0027 (6)
C5	0.0287 (8)	0.0389 (9)	0.0197 (8)	0.0053 (7)	0.0045 (6)	0.0125 (7)
C6	0.0252 (7)	0.0270 (7)	0.0234 (8)	0.0050 (6)	0.0038 (6)	0.0101 (6)
C7	0.0176 (7)	0.0207 (7)	0.0188 (7)	0.0050 (5)	0.0031 (5)	0.0059 (5)
C8	0.0209 (7)	0.0205 (7)	0.0185 (7)	0.0070 (5)	0.0017 (5)	0.0072 (5)
C9	0.0221 (7)	0.0197 (7)	0.0208 (8)	0.0058 (5)	0.0009 (5)	0.0066 (6)
O1	0.0294 (6)	0.0188 (5)	0.0205 (6)	0.0055 (4)	−0.0005 (4)	0.0063 (4)
O2	0.0436 (7)	0.0221 (6)	0.0382 (7)	0.0073 (5)	−0.0006 (5)	0.0136 (5)

C1—O2	1.2007 (18)	C5—C6	1.388 (2)
C1—O1	1.3935 (17)	C5—H5	0.9500
C1—C2	1.465 (2)	C6—C7	1.393 (2)
C2—C3	1.389 (2)	C6—H6	0.9500
C2—C7	1.3914 (18)	C7—C8	1.4543 (19)
C3—C4	1.378 (2)	C8—C9	1.3447 (19)
C3—H3	0.9500	C8—O1	1.3944 (17)
C4—C5	1.405 (2)	C9—C9i	1.433 (3)
C4—H4	0.9500	C9—H9	0.9500
O2—C1—O1	120.77 (15)	C4—C5—H5	119.2
O2—C1—C2	132.22 (15)	C5—C6—C7	117.42 (14)
O1—C1—C2	107.01 (12)	C5—C6—H6	121.3
C3—C2—C7	122.43 (14)	C7—C6—H6	121.3
C3—C2—C1	129.48 (14)	C2—C7—C6	120.35 (14)
C7—C2—C1	108.08 (13)	C2—C7—C8	107.24 (13)
C4—C3—C2	117.22 (14)	C6—C7—C8	132.40 (13)
C4—C3—H3	121.4	C9—C8—O1	120.45 (13)
C2—C3—H3	121.4	C9—C8—C7	131.48 (13)
C3—C4—C5	120.95 (14)	O1—C8—C7	108.04 (11)
C3—C4—H4	119.5	C8—C9—C9i	124.02 (16)
C5—C4—H4	119.5	C8—C9—H9	118.0
C6—C5—C4	121.59 (15)	C9i—C9—H9	118.0
C6—C5—H5	119.2	C1—O1—C8	109.58 (12)
O2—C1—C2—C3	2.1 (3)	C5—C6—C7—C2	2.1 (2)
O1—C1—C2—C3	−177.95 (14)	C5—C6—C7—C8	−176.59 (13)
O2—C1—C2—C7	−177.93 (16)	C2—C7—C8—C9	−176.24 (14)
O1—C1—C2—C7	2.00 (15)	C6—C7—C8—C9	2.6 (3)
C7—C2—C3—C4	−0.7 (2)	C2—C7—C8—O1	1.63 (15)
C1—C2—C3—C4	179.22 (13)	C6—C7—C8—O1	−179.57 (13)
C2—C3—C4—C5	1.7 (2)	O1—C8—C9—C9i	−1.6 (3)
C3—C4—C5—C6	−0.8 (2)	C7—C8—C9—C9i	176.07 (16)
C4—C5—C6—C7	−1.1 (2)	O2—C1—O1—C8	178.96 (12)
C3—C2—C7—C6	−1.2 (2)	C2—C1—O1—C8	−0.98 (16)
C1—C2—C7—C6	178.83 (12)	C9—C8—O1—C1	177.79 (11)
C3—C2—C7—C8	177.76 (13)	C7—C8—O1—C1	−0.36 (16)
C1—C2—C7—C8	−2.20 (15)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O2ii	0.95	2.70	3.459 (2)	137
C5—H5···O1iii	0.95	2.66	3.406 (2)	136
C6—H6···O2iv	0.95	2.71	3.4700 (19)	138
C9—H9···O2iv	0.95	2.55	3.3209 (18)	139

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯O2i	0.95	2.70	3.459 (2)	137
C5—H5⋯O1ii	0.95	2.66	3.406 (2)	136
C6—H6⋯O2iii	0.95	2.71	3.4700 (19)	138
C9—H9⋯O2iii	0.95	2.55	3.3209 (18)	139

Symmetry codes: (i) ; (ii) ; (iii) .