3,8-Dimethyl-acenaphthyl-ene-1,2-dione.

In the title compound, C(14)H(10)O(2), the acenaphthene-quinone core is essentially planar, with an r.m.s. deviation of 0.0140 Å. In the crystal, mol-ecules are connected by π-π stacking inter-actions [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 = 210.22

Triclinic,

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[F 2 > 2σ(F 2)] = 0.052

wR(F 2) = 0.148

S = 1.09

1844 reflections

147 parameters

H-atom parameters constrained

Δρmax = 0.17 e Å−3

Δρmin = −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.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811028479/rz2626sup1.cif

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

Supplementary material file. DOI: 10.1107/S1600536811028479/rz2626Isup3.cml

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

C14H10O2	Z = 2
Mr = 210.22	F(000) = 220
Triclinic, P1	Dx = 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

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

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(Fo2) + (0.0592P)2 + 0.102P] where P = (Fo2 + 2Fc2)/3
1844 reflections	(Δ/σ)max < 0.001
147 parameters	Δρmax = 0.17 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	0.7750 (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*

	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)

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)