3,8-Dimethyl­acenaphthyl­ene-1,2-dione

He, S.

doi:10.1107/S1600536811028479

organic compounds

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ISSN: 2056-9890

Volume 67| Part 8| August 2011| Page o2130

doi:10.1107/S1600536811028479

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3,8-Dimethylacenaphthylene-1,2-dione

Shu-hua He ^a ^*

^aSchool of Chemistry and Chemical Engineering, Yangtze Normal University, Fuling 408100, Chongqing, People's Republic of China
^*Correspondence e-mail: lhshuhua@yahoo.com.cn

(Received 9 July 2011; accepted 15 July 2011; online 23 July 2011)

In the title compound, C₁₄H₁₀O₂, the acenaphthenequinone core is essentially planar, with an r.m.s. deviation of 0.0140 Å. In the crystal, molecules are connected by π–π stacking interactions [centroid–centroid distances = 3.766 (3), 3.839 (3) and 3.857 (3) Å], forming columns parallel to the a axis.

Related literature

For the synthesis and applications of corannulene (systematic name: dibenzo[ghi,mno]fluoranthene) and its derivatives, see: Wu & Siegel (2006 ); Tsefrikas & Scott (2006 ); Sygula (2011 ); Zabula et al. (2011 ); Barth & Lawton (1966 ); Scott et al. (1997 ). For the synthesis of the title compound, see: Guillermet et al. (2009 ); Seiders et al. (1999 ); Mori et al. (2007 ). For the structure of related compounds, see: Abdourazak et al. (1994 ); Mochida & Yoza (2010 ).

Experimental

Crystal data

C₁₄H₁₀O₂
M_r = 210.22
Triclinic, $[P \overline 1]$
a = 7.5415 (8) Å
b = 8.5562 (11) Å
c = 9.8925 (12) Å
α = 67.891 (11)°
β = 88.310 (9)°
γ = 63.998 (11)°
V = 524.45 (13) Å³
Z = 2
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 293 K
0.42 × 0.35 × 0.35 mm

Data collection

Agilent Xcalibur Eos diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010 ) T_min = 0.964, T_max = 1.000
3865 measured reflections
1844 independent reflections
1247 reflections with I > 2σ(I)
R_int = 0.021

Refinement

R[F² > 2σ(F²)] = 0.052
wR(F²) = 0.148
S = 1.09
1844 reflections
147 parameters
H-atom parameters constrained
Δρ_max = 0.17 e Å⁻³
Δρ_min = −0.17 e Å⁻³

Data collection: CrysAlis PRO (Agilent, 2010); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: OLEX2 (Dolomanov et al., 2009 ); software used to prepare material for publication: OLEX2.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811028479/rz2626sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811028479/rz2626Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811028479/rz2626Isup3.cml

checkCIF report

Comment top

Corannulene (IUPAC name: dibenzo[ghi,mno]fluoranthene) and its derivatives have triggered intense interest due to their unusual bowl-formed structure (Wu & Siegel, 2006; Tsefrikas & Scott, 2006). Recently, a number of novel corannulene derivatives with excellent optical properties have been reported (Sygula, 2011; Zabula et al., 2011). Up to now, different synthetic methods have been reported (Barth & Lawton, 1966; Scott et al., 1997). The title compound, the synthesis of which has been reported in literatures (Guillermet et al., 2009; Seiders et al., 1999; Mori et al., 2007), is an important intermediate in synthesizing corannulene and its derivatives. Based on the importance of the relationship between structures and properties, the crystal structure of the title compound is reported herein.

The title molecule (Fig. 1) possesses a pseudo-mirror plane and is substantially planar, with a r.m.s. deviation of 0.0140 Å and maximum displacement of 0.026 (3) Å for atom C8. The dihedral angles between the C1–C5 five membered ring and the C3–C4/C9–C12 and C4–C9 benzene rings are 1.42 (9) and 0.81 (9)°, respectively. The C13–C6–C5–C1, C13–C6–C7–C8, C14–C12–C3–C2 and C14–C12–C11-C10 torsion angles are 3.6 (5), 178.4 (3), 0.4 (5) and 178.5 (4)°, respectively. As already observed in related compounds (Abdourazak et al., 1994; Mochida & Yoza, 2010), the C1–C2 bond length (1.569 (4) Å) is remarkably longer than expected for a C(sp^{2)– C(}^sp2) bond, and the bond angles involving the carbonyl groups ( O1—C1—C5 = 130.6 (3)°, O1—C1—C2 = 123.5 (2)°, C6—C5—C1 = 133.3 (2)°) are larger than the ideal value of 120°. In the crystal (Fig. 2), molecules are linked into columns parallel to the a axis by π–π stacking interactions [Cg1···Cg2ⁱ = 3.766 (3) Å; Cg2···Cg2ⁱ = 3.839 (3) Å; Cg2···Cg2ⁱⁱ = 3.857 (3) Å; Cg1 and Cg2 are the centroids of the C3–C4/C9–C12 and C4–C9 rings, respectively. Symmetry codes: (i) 2-x, 1-y, 2-z; (ii) 1-x, 1-y, 2-z].

Related literature top

For the synthesis and applications of corannulene (systematic name: dibenzo[ghi,mno]fluoranthene) and its derivatives, see: Wu & Siegel (2006); Tsefrikas & Scott (2006); Sygula (2011); Zabula et al. (2011); Barth & Lawton (1966); Scott et al. (1997). For the synthesis of the title compound, see: Guillermet et al. (2009); Seiders et al. (1999); Mori et al. (2007). For the structure of related compounds, see: Abdourazak et al. (1994); Mochida & Yoza (2010).

Experimental top

To a mixture of aluminium tribromide (10 g, 37.5 mmol) in CH₂Cl₂ (200 ml) was added dropwise a solution of 2,7-dimethylnaphthalene (2.6 g, 16.6 mmol) and oxalylchloride (2.2 ml, 26.0 mmol) in CH₂Cl₂ (150 ml) at about 253 K over 15 min. The mixture was stirred vigously at 253 K for additional 6 h and then quenched carefully by pouring into 500 ml ice water. After 30 min, the organic layer was washed with water, dried over MgSO₄, filtered and evaporated. The residue was dissolved in a minimal amount of CH₂Cl₂ and eluted with CH₂Cl₂/hexane (1:1 v/v) though an alumina column to give the title compound as a bright yellow solid (1.26 g, 37% yield, m.p. 478–480 K). Bright yellow single crystals suitable for X-ray diffraction were obtained at room temperature by slow evaporation of a CH₂Cl₂ solution over a period of several days.

Computing details top

Data collection: CrysAlis PRO (Agilent, 2010); cell refinement: CrysAlis PRO (Agilent, 2010); data reduction: CrysAlis PRO (Agilent, 2010); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

Figures top

	Fig. 1. The molecular structure of the title compound, with displacement ellipsoids drawn at the 30% probability level.
	Fig. 2. Packing diagram of the title compound. Displacement ellipsoids are drawn at the 30% probability level.

3,8-Dimethylacenaphthylene-1,2-dione top

Crystal data top

C₁₄H₁₀O₂	Z = 2
M_r = 210.22	F(000) = 220
Triclinic, P1	D_x = 1.331 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.7107 Å
a = 7.5415 (8) Å	Cell parameters from 1026 reflections
b = 8.5562 (11) Å	θ = 2.9–29.4°
c = 9.8925 (12) Å	µ = 0.09 mm⁻¹
α = 67.891 (11)°	T = 293 K
β = 88.310 (9)°	Block, yellow
γ = 63.998 (11)°	0.42 × 0.35 × 0.35 mm
V = 524.45 (13) Å³

Data collection top

Agilent Xcalibur Eos diffractometer	1844 independent reflections
Radiation source: Enhance (Mo) X-ray Source	1247 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.021
ω scans	θ_max = 25.0°, θ_min = 2.9°
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	h = −8→8
T_min = 0.964, T_max = 1.000	k = −9→10
3865 measured reflections	l = −11→11

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)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.148	H-atom parameters constrained
S = 1.09	w = 1/[σ²(F_o²) + (0.0592P)² + 0.102P] where P = (F_o² + 2F_c²)/3
1844 reflections	(Δ/σ)_max < 0.001
147 parameters	Δρ_max = 0.17 e Å⁻³
0 restraints	Δρ_min = −0.17 e Å⁻³

Crystal data top

C₁₄H₁₀O₂	γ = 63.998 (11)°
M_r = 210.22	V = 524.45 (13) Å³
Triclinic, P1	Z = 2
a = 7.5415 (8) Å	Mo Kα radiation
b = 8.5562 (11) Å	µ = 0.09 mm⁻¹
c = 9.8925 (12) Å	T = 293 K
α = 67.891 (11)°	0.42 × 0.35 × 0.35 mm
β = 88.310 (9)°

Data collection top

Agilent Xcalibur Eos diffractometer	1844 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	1247 reflections with I > 2σ(I)
T_min = 0.964, T_max = 1.000	R_int = 0.021
3865 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.052	0 restraints
wR(F²) = 0.148	H-atom parameters constrained
S = 1.09	Δρ_max = 0.17 e Å⁻³
1844 reflections	Δρ_min = −0.17 e Å⁻³
147 parameters

Special details top

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
O1	0.7750 (3)	0.0525 (3)	1.0053 (3)	0.0920 (7)
O2	0.7510 (3)	0.2516 (3)	0.6896 (3)	0.0968 (8)
C1	0.7662 (3)	0.2086 (3)	0.9497 (3)	0.0640 (8)
C2	0.7529 (3)	0.3165 (4)	0.7793 (3)	0.0652 (7)
C3	0.7426 (3)	0.4999 (3)	0.7582 (3)	0.0507 (6)
C4	0.7488 (3)	0.5024 (3)	0.8994 (2)	0.0425 (5)
C5	0.7647 (3)	0.3356 (3)	1.0170 (3)	0.0480 (6)
C6	0.7721 (3)	0.3212 (3)	1.1597 (3)	0.0545 (7)
C7	0.7594 (3)	0.4792 (4)	1.1814 (3)	0.0584 (7)
H7	0.7629	0.4727	1.2774	0.070*
C8	0.7422 (3)	0.6419 (3)	1.0686 (3)	0.0531 (6)
H8	0.7337	0.7421	1.0895	0.064*
C9	0.7374 (3)	0.6586 (3)	0.9216 (3)	0.0446 (6)
C10	0.7241 (3)	0.8142 (3)	0.7938 (3)	0.0547 (6)
H10	0.7177	0.9209	0.8026	0.066*
C11	0.7205 (4)	0.8089 (4)	0.6583 (3)	0.0616 (7)
H11	0.7125	0.9134	0.5769	0.074*
C12	0.7283 (3)	0.6538 (4)	0.6344 (3)	0.0592 (7)
C13	0.7965 (4)	0.1452 (4)	1.2891 (3)	0.0820 (9)
H13A	0.7773	0.1705	1.3765	0.123*
H13B	0.9284	0.0439	1.3032	0.123*
H13C	0.6992	0.1088	1.2703	0.123*
C14	0.7185 (5)	0.6599 (5)	0.4806 (3)	0.0916 (10)
H14A	0.7763	0.7373	0.4208	0.137*
H14B	0.5815	0.7129	0.4380	0.137*
H14C	0.7915	0.5333	0.4849	0.137*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0767 (13)	0.0459 (11)	0.160 (2)	−0.0320 (10)	0.0113 (13)	−0.0430 (12)
O2	0.0918 (15)	0.0941 (15)	0.1333 (19)	−0.0328 (12)	0.0040 (13)	−0.0859 (16)
C1	0.0407 (13)	0.0435 (14)	0.112 (2)	−0.0185 (11)	0.0053 (14)	−0.0368 (15)
C2	0.0447 (14)	0.0609 (16)	0.102 (2)	−0.0178 (12)	0.0048 (13)	−0.0525 (17)
C3	0.0407 (12)	0.0524 (14)	0.0655 (16)	−0.0182 (11)	0.0054 (11)	−0.0340 (13)
C4	0.0320 (11)	0.0403 (12)	0.0601 (15)	−0.0167 (9)	0.0068 (10)	−0.0251 (11)
C5	0.0362 (12)	0.0374 (12)	0.0707 (17)	−0.0182 (10)	0.0073 (11)	−0.0204 (12)
C6	0.0374 (13)	0.0507 (14)	0.0635 (17)	−0.0185 (11)	0.0077 (11)	−0.0134 (12)
C7	0.0515 (14)	0.0681 (17)	0.0553 (16)	−0.0239 (13)	0.0090 (12)	−0.0292 (14)
C8	0.0517 (14)	0.0504 (14)	0.0665 (17)	−0.0219 (12)	0.0078 (12)	−0.0345 (13)
C9	0.0379 (11)	0.0395 (12)	0.0596 (15)	−0.0178 (9)	0.0055 (10)	−0.0233 (11)
C10	0.0543 (14)	0.0414 (13)	0.0690 (18)	−0.0252 (11)	0.0020 (12)	−0.0186 (12)
C11	0.0575 (15)	0.0549 (15)	0.0617 (18)	−0.0273 (13)	0.0039 (12)	−0.0108 (13)
C12	0.0447 (14)	0.0706 (17)	0.0581 (16)	−0.0205 (12)	0.0043 (11)	−0.0289 (14)
C13	0.0662 (18)	0.0680 (18)	0.080 (2)	−0.0287 (15)	0.0118 (15)	−0.0004 (16)
C14	0.087 (2)	0.114 (3)	0.064 (2)	−0.031 (2)	0.0055 (16)	−0.0442 (19)

Geometric parameters (Å, º) top

O1—C1	1.209 (3)	C8—H8	0.9300
O2—C2	1.214 (3)	C8—C9	1.407 (3)
C1—C2	1.569 (4)	C9—C10	1.416 (3)
C1—C5	1.468 (3)	C10—H10	0.9300
C2—C3	1.470 (3)	C10—C11	1.360 (3)
C3—C4	1.407 (3)	C11—H11	0.9300
C3—C12	1.384 (3)	C11—C12	1.410 (3)
C4—C5	1.419 (3)	C12—C14	1.506 (4)
C4—C9	1.401 (3)	C13—H13A	0.9600
C5—C6	1.370 (3)	C13—H13B	0.9600
C6—C7	1.410 (3)	C13—H13C	0.9600
C6—C13	1.504 (3)	C14—H14A	0.9600
C7—H7	0.9300	C14—H14B	0.9600
C7—C8	1.372 (3)	C14—H14C	0.9600

O1—C1—C2	123.5 (2)	C4—C9—C8	116.2 (2)
O1—C1—C5	130.6 (3)	C4—C9—C10	116.3 (2)
C5—C1—C2	105.9 (2)	C8—C9—C10	127.5 (2)
O2—C2—C1	123.5 (2)	C9—C10—H10	119.7
O2—C2—C3	130.3 (3)	C11—C10—C9	120.5 (2)
C3—C2—C1	106.2 (2)	C11—C10—H10	119.7
C4—C3—C2	106.6 (2)	C10—C11—H11	118.2
C12—C3—C2	133.0 (2)	C10—C11—C12	123.6 (2)
C12—C3—C4	120.4 (2)	C12—C11—H11	118.2
C3—C4—C5	114.79 (19)	C3—C12—C11	116.6 (2)
C9—C4—C3	122.5 (2)	C3—C12—C14	122.7 (2)
C9—C4—C5	122.7 (2)	C11—C12—C14	120.7 (3)
C4—C5—C1	106.5 (2)	C6—C13—H13A	109.5
C6—C5—C1	133.3 (2)	C6—C13—H13B	109.5
C6—C5—C4	120.2 (2)	C6—C13—H13C	109.5
C5—C6—C7	116.9 (2)	H13A—C13—H13B	109.5
C5—C6—C13	122.5 (2)	H13A—C13—H13C	109.5
C7—C6—C13	120.6 (2)	H13B—C13—H13C	109.5
C6—C7—H7	118.3	C12—C14—H14A	109.5
C8—C7—C6	123.5 (2)	C12—C14—H14B	109.5
C8—C7—H7	118.3	C12—C14—H14C	109.5
C7—C8—H8	119.7	H14A—C14—H14B	109.5
C7—C8—C9	120.5 (2)	H14A—C14—H14C	109.5
C9—C8—H8	119.7	H14B—C14—H14C	109.5

O1—C1—C2—O2	−0.2 (4)	C4—C3—C12—C14	−179.2 (2)
O1—C1—C2—C3	179.3 (2)	C4—C5—C6—C7	1.2 (3)
O1—C1—C5—C4	−179.0 (2)	C4—C5—C6—C13	−177.7 (2)
O1—C1—C5—C6	−0.1 (4)	C4—C9—C10—C11	0.7 (3)
O2—C2—C3—C4	179.5 (3)	C5—C1—C2—O2	179.9 (2)
O2—C2—C3—C12	−0.2 (4)	C5—C1—C2—C3	−0.5 (2)
C1—C2—C3—C4	0.0 (2)	C5—C4—C9—C8	−0.1 (3)
C1—C2—C3—C12	−179.7 (2)	C5—C4—C9—C10	179.39 (18)
C1—C5—C6—C7	−177.6 (2)	C5—C6—C7—C8	−0.6 (3)
C1—C5—C6—C13	3.5 (4)	C6—C7—C8—C9	−0.4 (3)
C2—C1—C5—C4	0.8 (2)	C7—C8—C9—C4	0.7 (3)
C2—C1—C5—C6	179.7 (2)	C7—C8—C9—C10	−178.7 (2)
C2—C3—C4—C5	0.6 (2)	C8—C9—C10—C11	−179.8 (2)
C2—C3—C4—C9	−178.55 (18)	C9—C4—C5—C1	178.21 (18)
C2—C3—C12—C11	179.6 (2)	C9—C4—C5—C6	−0.9 (3)
C2—C3—C12—C14	0.4 (4)	C9—C10—C11—C12	0.4 (4)
C3—C4—C5—C1	−1.0 (2)	C10—C11—C12—C3	−0.7 (4)
C3—C4—C5—C6	179.97 (18)	C10—C11—C12—C14	178.5 (2)
C3—C4—C9—C8	178.99 (19)	C12—C3—C4—C5	−179.64 (19)
C3—C4—C9—C10	−1.5 (3)	C12—C3—C4—C9	1.2 (3)
C4—C3—C12—C11	0.0 (3)	C13—C6—C7—C8	178.3 (2)

Experimental details

Crystal data
Chemical formula	C₁₄H₁₀O₂
M_r	210.22
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	7.5415 (8), 8.5562 (11), 9.8925 (12)
α, β, γ (°)	67.891 (11), 88.310 (9), 63.998 (11)
V (Å³)	524.45 (13)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.42 × 0.35 × 0.35

Data collection
Diffractometer	Agilent Xcalibur Eos diffractometer
Absorption correction	Multi-scan (CrysAlis PRO; Agilent, 2010)
T_min, T_max	0.964, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	3865, 1844, 1247
R_int	0.021
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.052, 0.148, 1.09
No. of reflections	1844
No. of parameters	147
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.17, −0.17

Computer programs: CrysAlis PRO (Agilent, 2010), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), OLEX2 (Dolomanov et al., 2009).

Acknowledgements

This work was supported by the FLKJ (No. 2010ABA1014).

References

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