3,3-Dimethyl-1,2,3,4,6,11-hexa-hydro-benzo[d]naphtho[2,3-b]furan-1,6,11-trione.

In the title compound, C(18)H(14)O(4), the cyclo-hexene ring adopts a sofa conformation. In the crystalline state, the mol-ecules are linked into a chain by weak inter-molecular C-H⋯O hydrogen bonds.

Related literature

For related literature, see: Correa & Romo (1966 ▶); Greve & Friedrichsen (2000 ▶); Hirai et al. (1999 ▶); Hu et al. (2005 ▶); Ito et al. (2000 ▶). For related structures, see: Goldstein et al. (1975 ▶); Park et al. (1992 ▶).

Experimental

Crystal data

C18H14O4

M = 294.29

Triclinic,

a = 5.8080 (12) Å

b = 6.7510 (14) Å

c = 18.332 (4) Å

α = 89.82 (3)°

β = 81.32 (3)°

γ = 78.18 (3)°

V = 695.2 (2) Å3

Z = 2

Mo Kα radiation

μ = 0.10 mm−1

T = 293 (2) K

0.25 × 0.18 × 0.16 mm

Data collection

Bruker APEX CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2000 ▶) T min = 0.976, T max = 0.984

2958 measured reflections

2676 independent reflections

1845 reflections with I > 2σ(I)

R int = 0.018

Refinement

R[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.137

S = 1.07

2676 reflections

199 parameters

H-atom parameters constrained

Δρmax = 0.16 e Å−3

Δρmin = −0.23 e Å−3

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SMART; data reduction: SAINT (Bruker, 2000 ▶); program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808021600/bt2746sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808021600/bt2746Isup2.hkl

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

C18H14O4	Z = 2
Mr = 294.29	F000 = 308
Triclinic, P1	Dx = 1.406 Mg m−3
Hall symbol: -P 1	Mo Kα radiation λ = 0.71073 Å
a = 5.8080 (12) Å	Cell parameters from 810 reflections
b = 6.7510 (14) Å	θ = 2.5–28.0º
c = 18.332 (4) Å	µ = 0.10 mm−1
α = 89.82 (3)º	T = 293 (2) K
β = 81.32 (3)º	Block, yellow
γ = 78.18 (3)º	0.25 × 0.18 × 0.16 mm
V = 695.2 (2) Å3

Bruker APEX CCD diffractometer	2676 independent reflections
Radiation source: fine-focus sealed tube	1845 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.018
T = 293(2) K	θmax = 26.0º
φ and ω scans	θmin = 1.1º
Absorption correction: multi-scan(SADABS; Sheldrick, 2000)	h = 0→6
Tmin = 0.976, Tmax = 0.984	k = −8→8
2958 measured reflections	l = −21→21

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.047	H-atom parameters constrained
wR(F2) = 0.137	w = 1/[σ2(Fo2) + (0.0661P)2 + 0.1193P] where P = (Fo2 + 2Fc2)/3
S = 1.08	(Δ/σ)max < 0.001
2676 reflections	Δρmax = 0.16 e Å−3
199 parameters	Δρmin = −0.23 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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	−0.1220 (3)	1.1681 (3)	0.34222 (12)	0.0843 (7)
O2	0.6416 (2)	0.9262 (2)	0.22339 (7)	0.0410 (4)
O3	0.0036 (3)	1.4623 (2)	0.22564 (10)	0.0632 (5)
O4	0.9115 (3)	1.1186 (2)	0.11462 (10)	0.0632 (5)
C1	0.2866 (5)	0.5132 (4)	0.41299 (15)	0.0674 (7)
H1A	0.4384	0.4486	0.4254	0.081*
H1B	0.2448	0.4330	0.3759	0.081*
H1C	0.1680	0.5262	0.4562	0.081*
C2	0.3705 (4)	0.8498 (4)	0.44217 (13)	0.0619 (7)
H2A	0.5219	0.7838	0.4545	0.074*
H2B	0.2523	0.8649	0.4856	0.074*
H2C	0.3812	0.9809	0.4232	0.074*
C3	0.3004 (4)	0.7223 (3)	0.38363 (12)	0.0463 (5)
C4	0.0571 (4)	0.8275 (4)	0.36332 (13)	0.0531 (6)
H4A	0.0099	0.7383	0.3296	0.064*
H4B	−0.0597	0.8444	0.4078	0.064*
C5	0.0481 (3)	1.0297 (4)	0.32872 (12)	0.0498 (6)
C6	0.2637 (3)	1.0420 (3)	0.27647 (11)	0.0406 (5)
C7	0.4580 (3)	0.8876 (3)	0.27275 (11)	0.0381 (5)
C8	0.4861 (3)	0.6996 (3)	0.31386 (11)	0.0413 (5)
H8A	0.6445	0.6671	0.3273	0.050*
H8B	0.4679	0.5893	0.2829	0.050*
C9	0.5599 (3)	1.1101 (3)	0.19527 (11)	0.0394 (5)
C10	0.3304 (3)	1.1890 (3)	0.22546 (11)	0.0394 (5)
C11	0.2091 (3)	1.3861 (3)	0.20166 (11)	0.0419 (5)
C12	0.3557 (3)	1.4922 (3)	0.14706 (11)	0.0407 (5)
C13	0.5943 (3)	1.4062 (3)	0.11906 (11)	0.0405 (5)
C14	0.7101 (3)	1.2020 (3)	0.14072 (12)	0.0430 (5)
C15	0.2569 (4)	1.6823 (3)	0.12476 (12)	0.0489 (6)
H15A	0.0991	1.7403	0.1428	0.059*
C16	0.3895 (4)	1.7868 (3)	0.07620 (13)	0.0556 (6)
H16A	0.3205	1.9141	0.0612	0.067*
C17	0.6245 (4)	1.7035 (3)	0.04972 (13)	0.0568 (6)
H17A	0.7148	1.7752	0.0176	0.068*
C18	0.7246 (4)	1.5134 (3)	0.07112 (12)	0.0497 (5)
H18A	0.8827	1.4568	0.0529	0.060*

	U11	U22	U33	U12	U13	U23
O1	0.0402 (10)	0.0837 (13)	0.1077 (16)	0.0104 (9)	0.0245 (10)	0.0054 (11)
O2	0.0272 (7)	0.0433 (8)	0.0473 (8)	−0.0004 (6)	0.0012 (6)	0.0034 (6)
O3	0.0309 (8)	0.0669 (11)	0.0782 (12)	0.0111 (7)	0.0054 (8)	0.0014 (8)
O4	0.0357 (8)	0.0517 (9)	0.0847 (12)	0.0102 (7)	0.0190 (8)	0.0122 (8)
C1	0.0565 (15)	0.0743 (18)	0.0711 (17)	−0.0243 (13)	0.0057 (13)	0.0130 (13)
C2	0.0604 (15)	0.0814 (18)	0.0472 (13)	−0.0245 (13)	−0.0052 (11)	−0.0070 (12)
C3	0.0344 (11)	0.0585 (13)	0.0481 (12)	−0.0174 (9)	−0.0019 (9)	−0.0011 (10)
C4	0.0285 (11)	0.0664 (15)	0.0640 (15)	−0.0170 (10)	0.0045 (10)	−0.0065 (11)
C5	0.0266 (11)	0.0655 (14)	0.0547 (13)	−0.0084 (10)	0.0004 (9)	−0.0064 (11)
C6	0.0267 (10)	0.0484 (12)	0.0454 (12)	−0.0058 (8)	−0.0037 (8)	−0.0069 (9)
C7	0.0270 (10)	0.0463 (11)	0.0404 (11)	−0.0089 (8)	−0.0017 (8)	−0.0037 (9)
C8	0.0311 (10)	0.0475 (12)	0.0456 (12)	−0.0102 (8)	−0.0043 (9)	−0.0014 (9)
C9	0.0290 (10)	0.0403 (11)	0.0444 (11)	0.0014 (8)	−0.0032 (8)	−0.0013 (9)
C10	0.0268 (10)	0.0455 (11)	0.0426 (11)	−0.0011 (8)	−0.0034 (8)	−0.0079 (9)
C11	0.0277 (10)	0.0472 (12)	0.0454 (12)	0.0046 (8)	−0.0052 (8)	−0.0104 (9)
C12	0.0334 (10)	0.0435 (11)	0.0416 (11)	0.0033 (8)	−0.0095 (9)	−0.0073 (9)
C13	0.0336 (10)	0.0414 (11)	0.0416 (11)	0.0030 (8)	−0.0047 (8)	−0.0030 (8)
C14	0.0301 (10)	0.0427 (11)	0.0501 (12)	0.0008 (8)	0.0013 (9)	−0.0024 (9)
C15	0.0392 (11)	0.0472 (12)	0.0535 (13)	0.0085 (9)	−0.0093 (10)	−0.0057 (10)
C16	0.0558 (14)	0.0440 (12)	0.0605 (15)	0.0064 (10)	−0.0111 (12)	0.0029 (10)
C17	0.0540 (14)	0.0496 (13)	0.0616 (15)	−0.0021 (11)	−0.0041 (12)	0.0078 (11)
C18	0.0384 (11)	0.0490 (12)	0.0548 (13)	0.0015 (9)	0.0006 (10)	0.0039 (10)

O1—C5	1.208 (3)	C6—C10	1.432 (3)
O2—C7	1.358 (2)	C7—C8	1.467 (3)
O2—C9	1.364 (2)	C8—H8A	0.9700
O3—C11	1.214 (2)	C8—H8B	0.9700
O4—C14	1.216 (2)	C9—C10	1.362 (3)
C1—C3	1.522 (3)	C9—C14	1.449 (3)
C1—H1A	0.9600	C10—C11	1.470 (3)
C1—H1B	0.9600	C11—C12	1.492 (3)
C1—H1C	0.9600	C12—C15	1.382 (3)
C2—C3	1.530 (3)	C12—C13	1.406 (3)
C2—H2A	0.9600	C13—C18	1.374 (3)
C2—H2B	0.9600	C13—C14	1.486 (3)
C2—H2C	0.9600	C15—C16	1.377 (3)
C3—C8	1.530 (3)	C15—H15A	0.9300
C3—C4	1.545 (3)	C16—C17	1.379 (3)
C4—C5	1.498 (3)	C16—H16A	0.9300
C4—H4A	0.9700	C17—C18	1.378 (3)
C4—H4B	0.9700	C17—H17A	0.9300
C5—C6	1.474 (3)	C18—H18A	0.9300
C6—C7	1.364 (3)
C7—O2—C9	105.92 (14)	C7—C8—H8A	109.6
C3—C1—H1A	109.5	C3—C8—H8A	109.6
C3—C1—H1B	109.5	C7—C8—H8B	109.6
H1A—C1—H1B	109.5	C3—C8—H8B	109.6
C3—C1—H1C	109.5	H8A—C8—H8B	108.1
H1A—C1—H1C	109.5	C10—C9—O2	111.59 (18)
H1B—C1—H1C	109.5	C10—C9—C14	126.95 (19)
C3—C2—H2A	109.5	O2—C9—C14	121.46 (16)
C3—C2—H2B	109.5	C9—C10—C6	105.23 (18)
H2A—C2—H2B	109.5	C9—C10—C11	119.84 (19)
C3—C2—H2C	109.5	C6—C10—C11	134.92 (17)
H2A—C2—H2C	109.5	O3—C11—C10	122.8 (2)
H2B—C2—H2C	109.5	O3—C11—C12	121.16 (19)
C1—C3—C8	109.05 (18)	C10—C11—C12	116.04 (16)
C1—C3—C2	109.7 (2)	C15—C12—C13	118.9 (2)
C8—C3—C2	109.88 (17)	C15—C12—C11	119.26 (18)
C1—C3—C4	109.92 (18)	C13—C12—C11	121.79 (18)
C8—C3—C4	108.39 (18)	C18—C13—C12	119.57 (19)
C2—C3—C4	109.86 (19)	C18—C13—C14	119.02 (18)
C5—C4—C3	115.97 (17)	C12—C13—C14	121.41 (19)
C5—C4—H4A	108.3	O4—C14—C9	122.99 (19)
C3—C4—H4A	108.3	O4—C14—C13	123.17 (19)
C5—C4—H4B	108.3	C9—C14—C13	113.84 (16)
C3—C4—H4B	108.3	C16—C15—C12	120.7 (2)
H4A—C4—H4B	107.4	C16—C15—H15A	119.6
O1—C5—C6	123.7 (2)	C12—C15—H15A	119.6
O1—C5—C4	122.6 (2)	C15—C16—C17	120.2 (2)
C6—C5—C4	113.70 (18)	C15—C16—H16A	119.9
C7—C6—C10	106.29 (17)	C17—C16—H16A	119.9
C7—C6—C5	118.9 (2)	C18—C17—C16	119.6 (2)
C10—C6—C5	134.80 (19)	C18—C17—H17A	120.2
O2—C7—C6	110.97 (18)	C16—C17—H17A	120.2
O2—C7—C8	120.29 (16)	C13—C18—C17	120.9 (2)
C6—C7—C8	128.74 (18)	C13—C18—H18A	119.5
C7—C8—C3	110.45 (17)	C17—C18—H18A	119.5
C1—C3—C4—C5	−175.99 (19)	C5—C6—C10—C11	−2.8 (4)
C8—C3—C4—C5	−56.9 (2)	C9—C10—C11—O3	178.7 (2)
C2—C3—C4—C5	63.2 (2)	C6—C10—C11—O3	−0.3 (4)
C3—C4—C5—O1	−142.1 (2)	C9—C10—C11—C12	−2.9 (3)
C3—C4—C5—C6	38.6 (3)	C6—C10—C11—C12	178.1 (2)
O1—C5—C6—C7	171.1 (2)	O3—C11—C12—C15	1.5 (3)
C4—C5—C6—C7	−9.6 (3)	C10—C11—C12—C15	−177.03 (17)
O1—C5—C6—C10	−6.8 (4)	O3—C11—C12—C13	179.7 (2)
C4—C5—C6—C10	172.5 (2)	C10—C11—C12—C13	1.2 (3)
C9—O2—C7—C6	−0.1 (2)	C15—C12—C13—C18	0.8 (3)
C9—O2—C7—C8	−179.77 (17)	C11—C12—C13—C18	−177.42 (19)
C10—C6—C7—O2	0.0 (2)	C15—C12—C13—C14	−179.75 (18)
C5—C6—C7—O2	−178.41 (17)	C11—C12—C13—C14	2.0 (3)
C10—C6—C7—C8	179.67 (19)	C10—C9—C14—O4	−177.5 (2)
C5—C6—C7—C8	1.2 (3)	O2—C9—C14—O4	3.3 (3)
O2—C7—C8—C3	159.23 (17)	C10—C9—C14—C13	1.8 (3)
C6—C7—C8—C3	−20.4 (3)	O2—C9—C14—C13	−177.40 (17)
C1—C3—C8—C7	164.09 (18)	C18—C13—C14—O4	−4.7 (3)
C2—C3—C8—C7	−75.6 (2)	C12—C13—C14—O4	175.9 (2)
C4—C3—C8—C7	44.4 (2)	C18—C13—C14—C9	176.00 (19)
C7—O2—C9—C10	0.1 (2)	C12—C13—C14—C9	−3.4 (3)
C7—O2—C9—C14	179.43 (18)	C13—C12—C15—C16	−0.3 (3)
O2—C9—C10—C6	−0.1 (2)	C11—C12—C15—C16	178.01 (19)
C14—C9—C10—C6	−179.36 (19)	C12—C15—C16—C17	−0.7 (3)
O2—C9—C10—C11	−179.37 (16)	C15—C16—C17—C18	1.2 (4)
C14—C9—C10—C11	1.4 (3)	C12—C13—C18—C17	−0.4 (3)
C7—C6—C10—C9	0.0 (2)	C14—C13—C18—C17	−179.8 (2)
C5—C6—C10—C9	178.1 (2)	C16—C17—C18—C13	−0.6 (4)
C7—C6—C10—C11	179.2 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C16—H16A···O4i	0.93	2.54	3.177 (3)	126

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C16—H16A⋯O4i	0.93	2.54	3.177 (3)	126

Symmetry code: (i) .