8,8-Diethyl-1,4,5,8-tetra-hydro-naphthalene-1,4,5-trione.

The title mol-ecule, C(14)H(14)O(3), contains two fused six-membered carbon rings with keto groups at positions 1, 4 and 5 and a gem-diethyl group at position 8. The mol-ecule is close to planar (maximum deviation = 0.044 Å), with one ethyl group at each side of the mol-ecular plane, with exception of the keto group at position 1 which is slightly deviated from the plane and disordered over two positions one on each side of it (occupancies 0.80/0.20). The packing of the mol-ecule shows weak bonded chains along a through C-H⋯O contacts and two intramolecular C-H⋯O interactions are also present.

Related literature

For the biologically active dimethyl analog, see: Araya-Maturana et al. (2002 ▶); for its use as a substrate for Diels-Alder cyclo­additions with 2,4-hexa­dienol, see: Araya-Maturana et al. (1999 ▶) and for the synthesis of biologically active compounds, see: Araya-Maturana et al. (2006 ▶); Mendoza et al. (2005 ▶); Rodríguez et al. (2007 ▶). For details of the synthesis of the 4,4-dimethyl analog, see: Castro et al. (1983 ▶); Vega et al. (2008 ▶).

Experimental

Crystal data

C14H14O3

M = 230.25

Orthorhombic,

a = 12.7454 (8) Å

b = 10.8015 (7) Å

c = 8.8598 (5) Å

V = 1219.72 (13) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 150 (2) K

0.49 × 0.48 × 0.46 mm

Data collection

Siemens SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 1999 ▶) T min = 0.958, T max = 0.961

6581 measured reflections

2159 independent reflections

2119 reflections with I > 2σ(I)

R int = 0.012

Refinement

R[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.099

S = 1.00

2159 reflections

166 parameters

15 restraints

H-atom parameters constrained

Δρmax = 0.26 e Å−3

Δρmin = −0.15 e Å−3

Data collection: SMART-NT (Bruker, 2001 ▶); cell refinement: SAINT-NT (Bruker, 1999 ▶); data reduction: SAINT-NT; program(s) used to solve structure: SHELXTL-NT (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL-NT; molecular graphics: SHELXTL-NT; software used to prepare material for publication: SHELXTL-NT.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809001755/gw2058sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809001755/gw2058Isup2.hkl

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

C14H14O3	F(000) = 488
Mr = 230.25	Dx = 1.254 Mg m−3
Orthorhombic, Pna21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 4760 reflections
a = 12.7454 (8) Å	θ = 24.9–50.1°
b = 10.8015 (7) Å	µ = 0.09 mm−1
c = 8.8598 (5) Å	T = 150 K
V = 1219.72 (13) Å3	Block, red
Z = 4	0.49 × 0.48 × 0.46 mm

Siemens SMART CCD area-detector diffractometer	2159 independent reflections
Radiation source: fine-focus sealed tube	2119 reflections with I > 2σ(I)
graphite	Rint = 0.012
φ and ω scans	θmax = 25.1°, θmin = 2.5°
Absorption correction: multi-scan (SADABS; Bruker, 1999)	h = −15→15
Tmin = 0.958, Tmax = 0.961	k = −12→12
6581 measured reflections	l = −10→10

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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.099	H-atom parameters constrained
S = 1.00	w = 1/[σ2(Fo2) + (0.0642P)2 + 0.3077P] where P = (Fo2 + 2Fc2)/3
2159 reflections	(Δ/σ)max < 0.001
166 parameters	Δρmax = 0.26 e Å−3
15 restraints	Δρmin = −0.15 e Å−3

Experimental. 0.3 ° between frames and 10 secs exposure (per frame)

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	Occ. (<1)
O1	0.05513 (10)	0.73723 (13)	0.2345 (2)	0.0588 (5)
C1	0.12734 (12)	0.80829 (16)	0.2581 (2)	0.0312 (4)
C2	0.23531 (13)	0.76647 (15)	0.24985 (19)	0.0298 (4)
H2	0.2495	0.6828	0.2240	0.036*
C3	0.31458 (12)	0.84252 (16)	0.2775 (2)	0.0298 (4)
H3	0.3834	0.8091	0.2713	0.036*
C4	0.30503 (12)	0.97639 (16)	0.3177 (2)	0.0264 (4)
C9	0.36538 (13)	1.04995 (17)	0.1926 (2)	0.0343 (4)
H9A	0.3713	1.1375	0.2244	0.041*
H9B	0.4373	1.0161	0.1842	0.041*
C10	0.31363 (17)	1.04521 (19)	0.0381 (2)	0.0428 (5)
H10A	0.3037	0.9587	0.0080	0.064*
H10B	0.3585	1.0871	−0.0358	0.064*
H10C	0.2454	1.0868	0.0426	0.064*
C11	0.36382 (13)	0.99525 (17)	0.4703 (2)	0.0341 (4)
H11A	0.4375	0.9680	0.4579	0.041*
H11B	0.3648	1.0847	0.4944	0.041*
C12	0.31612 (17)	0.92627 (19)	0.6018 (2)	0.0446 (5)
H12A	0.2431	0.9523	0.6151	0.067*
H12B	0.3559	0.9446	0.6938	0.067*
H12C	0.3185	0.8371	0.5818	0.067*
C4A	0.19164 (12)	1.01751 (15)	0.32711 (18)	0.0257 (3)
C5	0.17023 (12)	1.15035 (15)	0.3703 (2)	0.0302 (4)
O2	0.24055 (10)	1.22495 (10)	0.38734 (17)	0.0391 (3)
C6	0.05978 (14)	1.18870 (18)	0.3909 (3)	0.0440 (5)
H6	0.0453	1.2693	0.4283	0.053*
C7	−0.01884 (14)	1.11471 (18)	0.3592 (3)	0.0444 (5)
H7	−0.0887	1.1421	0.3759	0.053*
C8	−0.00040 (15)	0.9904 (2)	0.2982 (3)	0.0515 (6)
O3i	−0.07253 (14)	0.93529 (18)	0.2268 (3)	0.0604 (6)	0.80
O3ii	−0.0669 (5)	0.9189 (6)	0.3592 (11)	0.063 (2)	0.20
C8A	0.11022 (12)	0.94198 (15)	0.2963 (2)	0.0304 (4)

	U11	U22	U33	U12	U13	U23
O1	0.0288 (7)	0.0394 (7)	0.1082 (15)	−0.0062 (6)	−0.0007 (8)	−0.0163 (8)
C1	0.0240 (8)	0.0302 (8)	0.0396 (10)	−0.0027 (7)	0.0001 (7)	0.0002 (7)
C2	0.0308 (8)	0.0257 (8)	0.0329 (10)	0.0031 (6)	0.0016 (7)	−0.0017 (7)
C3	0.0214 (7)	0.0342 (8)	0.0338 (9)	0.0049 (6)	0.0014 (7)	0.0024 (7)
C4	0.0215 (7)	0.0294 (8)	0.0284 (8)	−0.0011 (6)	0.0010 (6)	0.0005 (7)
C9	0.0282 (8)	0.0360 (9)	0.0388 (10)	−0.0042 (7)	0.0057 (7)	0.0027 (7)
C10	0.0515 (12)	0.0436 (11)	0.0332 (10)	−0.0007 (9)	0.0069 (9)	0.0041 (8)
C11	0.0287 (8)	0.0394 (9)	0.0341 (9)	0.0005 (7)	−0.0061 (7)	−0.0012 (8)
C12	0.0541 (12)	0.0486 (11)	0.0311 (10)	0.0022 (9)	−0.0036 (9)	0.0016 (9)
C4A	0.0235 (7)	0.0284 (8)	0.0251 (8)	0.0014 (6)	−0.0006 (6)	0.0021 (6)
C5	0.0325 (8)	0.0293 (8)	0.0288 (8)	0.0035 (7)	−0.0009 (7)	0.0004 (7)
O2	0.0424 (7)	0.0303 (6)	0.0446 (8)	−0.0047 (5)	−0.0031 (6)	−0.0033 (6)
C6	0.0392 (10)	0.0339 (9)	0.0589 (13)	0.0110 (8)	0.0016 (10)	−0.0084 (10)
C7	0.0287 (9)	0.0454 (11)	0.0591 (12)	0.0122 (8)	0.0028 (9)	−0.0022 (9)
C8	0.0220 (8)	0.0379 (9)	0.0946 (17)	0.0012 (7)	0.0008 (10)	−0.0040 (11)
O3i	0.0286 (9)	0.0545 (11)	0.0980 (17)	0.0031 (8)	−0.0155 (11)	−0.0103 (12)
O3ii	0.016 (3)	0.050 (4)	0.122 (7)	−0.006 (3)	0.012 (4)	−0.032 (5)
C8A	0.0219 (8)	0.0308 (8)	0.0385 (9)	0.0031 (6)	0.0008 (7)	0.0020 (7)

O1—C1	1.217 (2)	C11—H11A	0.9900
C1—C2	1.450 (2)	C11—H11B	0.9900
C1—C8A	1.499 (2)	C12—H12A	0.9800
C2—C3	1.325 (2)	C12—H12B	0.9800
C2—H2	0.9500	C12—H12C	0.9800
C3—C4	1.494 (2)	C4A—C8A	1.348 (2)
C3—H3	0.9500	C4A—C5	1.510 (2)
C4—C4A	1.514 (2)	C5—O2	1.215 (2)
C4—C11	1.559 (2)	C5—C6	1.479 (2)
C4—C9	1.566 (2)	C6—C7	1.312 (3)
C9—C10	1.520 (3)	C6—H6	0.9500
C9—H9A	0.9900	C7—C8	1.467 (3)
C9—H9B	0.9900	C7—H7	0.9500
C10—H10A	0.9800	C8—O3i	1.264 (3)
C10—H10B	0.9800	C8—O3ii	1.267 (3)
C10—H10C	0.9800	C8—C8A	1.504 (2)
C11—C12	1.511 (3)
O1—C1—C2	120.84 (16)	C12—C11—H11B	108.7
O1—C1—C8A	122.44 (15)	C4—C11—H11B	108.7
C2—C1—C8A	116.72 (14)	H11A—C11—H11B	107.6
C3—C2—C1	121.40 (15)	C11—C12—H12A	109.5
C3—C2—H2	119.3	C11—C12—H12B	109.5
C1—C2—H2	119.3	H12A—C12—H12B	109.5
C2—C3—C4	125.59 (15)	C11—C12—H12C	109.5
C2—C3—H3	117.2	H12A—C12—H12C	109.5
C4—C3—H3	117.2	H12B—C12—H12C	109.5
C3—C4—C4A	112.01 (13)	C8A—C4A—C5	119.17 (14)
C3—C4—C11	107.09 (15)	C8A—C4A—C4	123.10 (14)
C4A—C4—C11	111.88 (13)	C5—C4A—C4	117.72 (13)
C3—C4—C9	106.41 (14)	O2—C5—C6	120.09 (15)
C4A—C4—C9	111.04 (13)	O2—C5—C4A	121.91 (14)
C11—C4—C9	108.14 (13)	C6—C5—C4A	118.00 (14)
C10—C9—C4	114.02 (15)	C7—C6—C5	122.00 (16)
C10—C9—H9A	108.7	C7—C6—H6	119.0
C4—C9—H9A	108.7	C5—C6—H6	119.0
C10—C9—H9B	108.7	C6—C7—C8	120.96 (16)
C4—C9—H9B	108.7	C6—C7—H7	119.5
H9A—C9—H9B	107.6	C8—C7—H7	119.5
C9—C10—H10A	109.5	O3i—C8—O3ii	56.0 (4)
C9—C10—H10B	109.5	O3i—C8—C7	119.90 (18)
H10A—C10—H10B	109.5	O3ii—C8—C7	107.1 (4)
C9—C10—H10C	109.5	O3i—C8—C8A	120.9 (2)
H10A—C10—H10C	109.5	O3ii—C8—C8A	114.8 (4)
H10B—C10—H10C	109.5	C7—C8—C8A	118.20 (17)
C12—C11—C4	114.25 (14)	C4A—C8A—C1	121.11 (14)
C12—C11—H11A	108.7	C4A—C8A—C8	120.61 (15)
C4—C11—H11A	108.7	C1—C8A—C8	118.27 (15)
O1—C1—C2—C3	−178.98 (19)	C4—C4A—C5—C6	−175.48 (16)
C8A—C1—C2—C3	1.2 (2)	O2—C5—C6—C7	173.1 (2)
C1—C2—C3—C4	−0.7 (3)	C4A—C5—C6—C7	−6.5 (3)
C2—C3—C4—C4A	1.2 (3)	C5—C6—C7—C8	−1.3 (3)
C2—C3—C4—C11	124.22 (18)	C6—C7—C8—O3i	−158.7 (3)
C2—C3—C4—C9	−120.31 (19)	C6—C7—C8—O3ii	141.2 (5)
C3—C4—C9—C10	68.10 (19)	C6—C7—C8—C8A	9.7 (3)
C4A—C4—C9—C10	−54.0 (2)	C5—C4A—C8A—C1	−177.87 (16)
C11—C4—C9—C10	−177.13 (15)	C4—C4A—C8A—C1	3.4 (3)
C3—C4—C11—C12	−64.03 (18)	C5—C4A—C8A—C8	2.6 (3)
C4A—C4—C11—C12	59.1 (2)	C4—C4A—C8A—C8	−176.14 (17)
C9—C4—C11—C12	−178.34 (15)	O1—C1—C8A—C4A	177.64 (19)
C3—C4—C4A—C8A	−2.6 (2)	C2—C1—C8A—C4A	−2.6 (2)
C11—C4—C4A—C8A	−122.82 (18)	O1—C1—C8A—C8	−2.9 (3)
C9—C4—C4A—C8A	116.25 (18)	C2—C1—C8A—C8	176.95 (18)
C3—C4—C4A—C5	178.65 (16)	O3i—C8—C8A—C4A	157.9 (2)
C11—C4—C4A—C5	58.39 (19)	O3ii—C8—C8A—C4A	−138.3 (5)
C9—C4—C4A—C5	−62.53 (18)	C7—C8—C8A—C4A	−10.3 (3)
C8A—C4A—C5—O2	−173.95 (17)	O3i—C8—C8A—C1	−21.6 (3)
C4—C4A—C5—O2	4.9 (2)	O3ii—C8—C8A—C1	42.2 (5)
C8A—C4A—C5—C6	5.7 (3)	C7—C8—C8A—C1	170.2 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O1i	0.95	2.27	3.207 (2)	169
C9—H9A···O2	0.99	2.40	3.014 (2)	120
C11—H11B···O2	0.99	2.39	3.027 (2)	122

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯O1i	0.95	2.27	3.207 (2)	169
C9—H9A⋯O2	0.99	2.40	3.014 (2)	120
C11—H11B⋯O2	0.99	2.39	3.027 (2)	122

Symmetry code: (i) .