3,3-Dimethyl-1,2,3,4,6,11-hexa­hydro­benzo[d]naphtho[2,3-b]furan-1,6,11-trione

Hu, H.

doi:10.1107/S1600536808021600

organic compounds

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Volume 64| Part 8| August 2008| Page o1534

doi:10.1107/S1600536808021600

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3,3-Dimethyl-1,2,3,4,6,11-hexahydrobenzo[d]naphtho[2,3-b]furan-1,6,11-trione

Huayou Hu ^a ^*

^aDepartment of Chemistry and Chemical Engineering, Southeast University, Nanjing, People's Republic of China
^*Correspondence e-mail: njuhhy@hotmail.com

(Received 11 July 2008; accepted 11 July 2008; online 19 July 2008)

In the title compound, C₁₈H₁₄O₄, the cyclohexene ring adopts a sofa conformation. In the crystalline state, the molecules are linked into a chain by weak intermolecular 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_r = 294.29
Triclinic, $[P \overline 1]$
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[F² > 2σ(F²)] = 0.047
wR(F²) = 0.137
S = 1.07
2676 reflections
199 parameters
H-atom parameters constrained
Δρ_max = 0.16 e Å⁻³
Δρ_min = −0.23 e Å⁻³

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) x-1, y+1, z.

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.

Supporting information

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

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

checkCIF report

Comment top

Furan derivatives and annulated furan derivatives widely occur in nature. Many of these naturally occurring furan and annulated furan derivatives and their unnatural analogs have a wide range of biological activity and are important precursors for the synthesis of natural products (Greve & Friedrichsen, 2000). Especially, naphtho[2,3-b]furan-4,9-dione derivatives as represented by avicequinones (Ito et al., 2000) and maturinones (Correa & Romo, 1966) have shown a diversity of biological activities of medical importance, such as anticancer, antibacterial and anti-inflammatory activity (Hirai et al., 1999). Recently, we had reported an one-pot synthesis method for naphtho[2,3-b]furan-4,9-dione derivatives by reacting 2,3-dichloro-1,4-naphthoquinone with 1,3-dicarbonyl compounds (Hu et al., 2005).

The title compound, C₁₈H₁₄O₄, is a naphtho[2,3-b]furan-4,9-dione derivative. It is formed as one product from refluxing 2,3-dichloro-1,4-naphthoquione, K₂CO₃ and 5,5-dimethylcyclohexane-1,3-dione in MeCN for 6 h. In the crystalline state, the molecules are linked to a one-dimensional chain by intermolecular weak C—H···O hydrogen bonds (Table 1).

Related literature top

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 top

A mixture of 2,3-dichloro-1,4-naphthoquione (0.227 g, 1.0 mmol), K₂CO₃ (0.345 g, 2.5 mmol) and 5,5-dimethylcyclohexane-1,3-dione (0.154 g, 1.1 mmol) in MeCN (15 ml) was stirred at reflux temperature for 6 h. The reaction mixture was poured into H₂O (150 ml) and filtered. The collected solid product was separated by silica gel column chromatography [petroleum ether - EtOAc (10:1)] yield the title compound (0.118 g, 40%) as a yellow solid. Single crystals suitable for X-ray crystallographic analysis were grown by slow evaporation of solvent from petroleum ether (b.p. 333–363 K)-ethyl acetate (3/1 v/v).

Computing details top

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

Figures top

	Fig. 1. The molecular structure of the title compound with 30% displacement ellipsoids.
	Fig. 2. Hydrogen-bonding of the title compound.

3,3-Dimethyl-1,2,3,4,6,11-hexahydrobenzo[d]naphtho[2,3-b]furan- 1,6,11-trione top

Crystal data top

C₁₈H₁₄O₄	Z = 2
M_r = 294.29	F(000) = 308
Triclinic, P1	D_x = 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 = 2.5–28.0°
c = 18.332 (4) Å	µ = 0.10 mm⁻¹
α = 89.82 (3)°	T = 293 K
β = 81.32 (3)°	Block, yellow
γ = 78.18 (3)°	0.25 × 0.18 × 0.16 mm
V = 695.2 (2) Å³

Data collection top

Bruker APEX CCD diffractometer	2676 independent reflections
Radiation source: fine-focus sealed tube	1845 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.018
ϕ and ω scans	θ_max = 26.0°, θ_min = 1.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 2000)	h = 0→6
T_min = 0.976, T_max = 0.984	k = −8→8
2958 measured reflections	l = −21→21

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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.137	H-atom parameters constrained
S = 1.08	w = 1/[σ²(F_o²) + (0.0661P)² + 0.1193P] where P = (F_o² + 2F_c²)/3
2676 reflections	(Δ/σ)_max < 0.001
199 parameters	Δρ_max = 0.16 e Å⁻³
0 restraints	Δρ_min = −0.23 e Å⁻³

Crystal data top

C₁₈H₁₄O₄	γ = 78.18 (3)°
M_r = 294.29	V = 695.2 (2) Å³
Triclinic, P1	Z = 2
a = 5.8080 (12) Å	Mo Kα radiation
b = 6.7510 (14) Å	µ = 0.10 mm⁻¹
c = 18.332 (4) Å	T = 293 K
α = 89.82 (3)°	0.25 × 0.18 × 0.16 mm
β = 81.32 (3)°

Data collection top

Bruker APEX CCD diffractometer	2676 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2000)	1845 reflections with I > 2σ(I)
T_min = 0.976, T_max = 0.984	R_int = 0.018
2958 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.047	0 restraints
wR(F²) = 0.137	H-atom parameters constrained
S = 1.08	Δρ_max = 0.16 e Å⁻³
2676 reflections	Δρ_min = −0.23 e Å⁻³
199 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	−0.1220 (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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) x−1, y+1, z.

Experimental details

Crystal data
Chemical formula	C₁₈H₁₄O₄
M_r	294.29
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	5.8080 (12), 6.7510 (14), 18.332 (4)
α, β, γ (°)	89.82 (3), 81.32 (3), 78.18 (3)
V (Å³)	695.2 (2)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.25 × 0.18 × 0.16

Data collection
Diffractometer	Bruker APEX CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2000)
T_min, T_max	0.976, 0.984
No. of measured, independent and observed [I > 2σ(I)] reflections	2958, 2676, 1845
R_int	0.018
(sin θ/λ)_max (Å⁻¹)	0.616

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.047, 0.137, 1.08
No. of reflections	2676
No. of parameters	199
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.16, −0.23

Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C16—H16A···O4ⁱ	0.93	2.54	3.177 (3)	125.7

Symmetry code: (i) x−1, y+1, z.

Acknowledgements

The author thanks the Program for Young Excellent Talents in Southeast University for financial support.

References

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