(3Z,3′Z)-3,3′-(Ethane-1,2-diyl­idene)­bis[isobenzofuran-1(3H)-one]

Ono, K.; Tokura, O.; Tomura, M.

doi:10.1107/S1600536809030888

organic compounds

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Volume 65| Part 9| September 2009| Page o2118

doi:10.1107/S1600536809030888

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(3Z,3′Z)-3,3′-(Ethane-1,2-diylidene)bis[isobenzofuran-1(3H)-one]

Katsuhiko Ono,^a ^* Osamu Tokura ^a and Masaaki Tomura ^b

^aDepartment of Materials Science and Engineering, Nagoya Institute of Technology, Gokiso, Showa-ku, Nagoya 466-8555, Japan, and ^bInstitute for Molecular Science, Myodaiji, Okazaki 444-8585, Japan
^*Correspondence e-mail: ono.katsuhiko@nitech.ac.jp

(Received 3 August 2009; accepted 4 August 2009; online 8 August 2009)

The title compound, C₁₈H₁₀O₄, has been isolated as an impurity in commercially available 6,11-dihydroxy-5,12-naphthacenedione. The title compound exhibits yellow fluorescence in the solid state. The molecule 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 interactions between 3-methyleneisobenzofuran-1(3H)-one units [interplanar 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_r = 290.26
Triclinic, $[P \overline 1]$
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[F² > 2σ(F²)] = 0.066
wR(F²) = 0.176
S = 0.97
1661 reflections
100 parameters
H-atom parameters constrained
Δρ_max = 0.35 e Å⁻³
Δρ_min = −0.28 e Å⁻³

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) -x+2, -y+2, -z+2; (ii) x, y, z+1; (iii) x, y-1, z.

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 ).

Supporting information

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

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

checkCIF report

Comment top

Through the study of the crystallographic analysis and functionalities of 6,11-dihydroxy-5,12-naphthacenedione (Tomura et al., 2008; Ono et al., 2009), we found the existence of a yellow fluorescent compound as a by-product in the commercially available chemical reagent. After the separation of the by-product, the structure was determined to be the title compound, (I). Although the synthesis of (I) was already reported (Ji et al., 2006), the characterization has not been performed. In this paper, we report the separation, spectral data, and molecular and crystal structures of (I).

The molecular structure of (I) is shown in Fig. 1. The molecule is centrosymmetric and planar with an r.m.s. deviation of 0.031 (1) Å. The distances of the C9—C9 (-x + 1, -y, -z + 1) and C8—C9 bonds are 1.433 (3) and 1.345 (2) Å, respectively, indicating a butadiene skeleton. The bond length of C1—O2 [1.201 (2) Å] is reasonable for carbonyl group. Further, the O1—C1 and O1—C8 bonds result in O—C single bonds with a bond distance of 1.394 (2) Å. These bond distances support the molecular structure of (I).

In the crystal structure, the molecules are linked to each other through intermolecular C—H···O interactions (Table 1). The molecular arrangements shown in Figs. 2 and 3 run stepwise along the b and c axes, respectively. Fig. 4 also exhibits a stepwise arrangement along the (021) direction with C—H···O contacts. Furthermore, the 3-methyleneisobenzofuran-1(3H)-one rings overlap each other to form a π-stacking structure with an interplanar distance of 3.43 Å, as shown in Fig. 5.

Related literature top

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 top

The commercially available 6,11-dihydroxy-5,12-naphthacenedione (100 mg, Aldrich) was recrystallized from ethyl acetate (280 ml) to afford pure red crystals of 6,11-dihydroxy-5,12-naphthacenedione (70 mg). The filtrate containing the title compound, (I) was concentrated, and the residue (25 mg) was dissolved in toluene (100 ml). The solution was washed with 1 M NaOH solutions (100 ml) ten times over until the NaOH solution was colorless. The organic solution was dried over Na₂SO₄ and concentrated to provide a yellow solid of (I) (ca 9% yield). Yellow prisms of the title compound, suitable for X-ray analysis were grown from a dichloromethane solution.

Computing details top

Data collection: CrystalClear (Rigaku/MSC, 2006); cell refinement: CrystalClear (Rigaku/MSC, 2006); data reduction: CrystalClear (Rigaku/MSC, 2006); 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).

Figures top

	Fig. 1. The molecular structure of (I), with atom labels and 50% probability displacement ellipsoids for non-H atoms and H atoms are shown as small spheres of arbitrary radii.
	Fig. 2. Aggregation along the b axis with C—H···O contacts.
	Fig. 3. Aggregation along the c axis with C—H···O contacts.
	Fig. 4. Aggregation along the (021) direction with C—H···O contacts.
	Fig. 5. π-Stacking structure with an interplanar distance of 3.43 Å.

(3Z,3'Z)-3,3'-(Ethane-1,2-diylidene)bis[isobenzofuran-1(3H)-one] top

Crystal data top

C₁₈H₁₀O₄	Z = 1
M_r = 290.26	F(000) = 150
Triclinic, P1	D_x = 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

Data collection top

Rigaku/MSC Mercury CCD diffractometer	1323 reflections with I > 2σ(I)
Radiation source: Rotating Anode	R_int = 0.044
Graphite Monochromator monochromator	θ_max = 30.8°, θ_min = 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 top

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(F_o²) + (0.1211P)²] where P = (F_o² + 2F_c²)/3
1661 reflections	(Δ/σ)_max < 0.001
100 parameters	Δρ_max = 0.35 e Å⁻³
0 restraints	Δρ_min = −0.28 e Å⁻³

Crystal data top

C₁₈H₁₀O₄	γ = 107.239 (8)°
M_r = 290.26	V = 324.53 (11) Å³
Triclinic, P1	Z = 1
a = 6.9030 (13) Å	Mo Kα radiation
b = 7.0374 (16) Å	µ = 0.11 mm⁻¹
c = 7.7792 (13) Å	T = 173 K
α = 112.190 (5)°	1.00 × 0.50 × 0.40 mm
β = 95.696 (2)°

Data collection top

Rigaku/MSC Mercury CCD diffractometer	1323 reflections with I > 2σ(I)
2656 measured reflections	R_int = 0.044
1661 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.066	0 restraints
wR(F²) = 0.176	H-atom parameters constrained
S = 0.97	Δρ_max = 0.35 e Å⁻³
1661 reflections	Δρ_min = −0.28 e Å⁻³
100 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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)

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Symmetry code: (i) −x+1, −y, −z+1.

Hydrogen-bond geometry (Å, º) top

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···O2^iv	0.95	2.71	3.4700 (19)	138
C9—H9···O2^iv	0.95	2.55	3.3209 (18)	139

Symmetry codes: (ii) −x+2, −y+2, −z+2; (iii) x, y, z+1; (iv) x, y−1, z.

Experimental details

Crystal data
Chemical formula	C₁₈H₁₀O₄
M_r	290.26
Crystal system, space group	Triclinic, P1
Temperature (K)	173
a, b, c (Å)	6.9030 (13), 7.0374 (16), 7.7792 (13)
α, β, γ (°)	112.190 (5), 95.696 (2), 107.239 (8)
V (Å³)	324.53 (11)
Z	1
Radiation type	Mo Kα
µ (mm⁻¹)	0.11
Crystal size (mm)	1.00 × 0.50 × 0.40

Data collection
Diffractometer	Rigaku/MSC Mercury CCD diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	2656, 1661, 1323
R_int	0.044
(sin θ/λ)_max (Å⁻¹)	0.719

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.066, 0.176, 0.97
No. of reflections	1661
No. of parameters	100
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.35, −0.28

Computer programs: CrystalClear (Rigaku/MSC, 2006), SIR2004 (Burla et al., 2005), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009) and Mercury (Macrae et al., 2006), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O2ⁱ	0.95	2.70	3.459 (2)	137.2
C5—H5···O1ⁱⁱ	0.95	2.66	3.406 (2)	135.5
C6—H6···O2ⁱⁱⁱ	0.95	2.71	3.4700 (19)	137.7
C9—H9···O2ⁱⁱⁱ	0.95	2.55	3.3209 (18)	138.6

Symmetry codes: (i) −x+2, −y+2, −z+2; (ii) x, y, z+1; (iii) x, y−1, z.

Acknowledgements

This work was supported by a Grant-in-Aid for Scientific Research (grant No. 20550037) from the Ministry of Education, Culture, Sports, Science and Technology, Japan. The authors thank the Instrument Center of the Institute for Molecular Science for the X-ray structure analysis.

References

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