7-Hydro­xy-2,2,7-tri­methyl­per­hydro­naphthalene-1,5-dione

The title compound, C₁₃H₂₀O₃, crystallizes as a racemic mixture in which the two enantiomeric forms of the mol­ecule are related by an inversion center. The crystal structure confirms the one proposed on the basis of spectroscopic data and provides the information required to assign the relative stereochemistry of the chiral centers of the mol­ecule. The crystal packing is directed by intermolecular hydrogen bonds and short intramolecular C—H...O contacts.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.051
• wR factor = 0.167
• Data-to-parameter ratio = 18.6

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Computing details

Data collection: (MSC/AFC Diffractometer Control Software; Molecular Structure Corporation, 1993); cell refinement: MSC/AFC Diffractometer Control Software; data reduction: MSC/AFC Diffractometer Control Software; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ZORTEP (Zsolnai & Pritzkow, 1995); software used to prepare material for publication: PLATON (Spek, 2003) and CSD (Allen, 2002).

7-Hydroxy-2,2,7-trimethylperhydronaphthalene-1,5-dione

Crystal data

C13H20O3	Z = 2
Mr = 224.29	F(000) = 244
Triclinic, P1	Dx = 1.235 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71069 Å
a = 6.0562 (13) Å	Cell parameters from 25 reflections
b = 9.827 (2) Å	θ = 35.0–47.5°
c = 11.1075 (16) Å	µ = 0.09 mm^−1
α = 109.289 (14)°	T = 293 K
β = 102.766 (15)°	Needle, colourless
γ = 92.771 (19)°	0.30 × 0.15 × 0.10 mm
V = 603.2 (2) Å^3

Data collection

Rigaku AFC-7S diffractometer	1951 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.030
Graphite monochromator	θmax = 27.5°, θmin = 2.0°
θ/2θ scans	h = −7→7
Absorption correction: ψ scan (MSC/AFC Diffractometer Control Software; Molecular Structure Corporation, 1993)	k = −2→12
Tmin = 0.965, Tmax = 0.991	l = −14→14
3565 measured reflections	3 standard reflections every 150 reflections
2768 independent reflections	intensity decay: 2.5%

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.051	H-atom parameters constrained
wR(F^2) = 0.167	w = 1/[σ^2(Fo^2) + (0.0851P)^2 + 0.1359P] where P = (Fo^2 + 2Fc^2)/3
S = 1.04	(Δ/σ)max < 0.001
2768 reflections	Δρmax = 0.39 e Å^−3
149 parameters	Δρmin = −0.20 e Å^−3
0 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.055 (11)

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
C1	0.2727 (3)	0.57127 (16)	0.84623 (15)	0.0386 (4)
C8	0.1039 (3)	0.32632 (16)	0.83823 (16)	0.0402 (4)
H8A	−0.0220	0.3697	0.8702	0.048*
H8B	0.2246	0.3314	0.9140	0.048*
C4'	0.3906 (3)	0.34550 (15)	0.70635 (14)	0.0352 (3)
H4'	0.5150	0.3486	0.7809	0.042*
C8'	0.1918 (3)	0.41197 (15)	0.76269 (14)	0.0341 (3)
H8'	0.0660	0.4078	0.6884	0.041*
C2	0.3659 (3)	0.66562 (16)	0.77882 (15)	0.0403 (4)
O1	0.2723 (3)	0.61833 (14)	0.96167 (13)	0.0643 (5)
C6	0.2187 (3)	0.09874 (16)	0.69435 (18)	0.0450 (4)
H6A	0.3416	0.0942	0.7651	0.054*
H6B	0.1631	0.0003	0.6336	0.054*
O2	0.3083 (2)	0.13662 (13)	0.50821 (12)	0.0541 (4)
C7	0.0236 (3)	0.16708 (16)	0.75157 (16)	0.0402 (4)
O3	−0.1584 (2)	0.16920 (12)	0.64581 (12)	0.0486 (3)
H3	−0.2073	0.0856	0.5959	0.058*
C4	0.4823 (3)	0.43198 (17)	0.63352 (16)	0.0437 (4)
H4A	0.3649	0.4266	0.5563	0.052*
H4B	0.6114	0.3903	0.6042	0.052*
C3	0.5567 (3)	0.59060 (18)	0.72207 (17)	0.0446 (4)
H3A	0.6099	0.6436	0.6719	0.054*
H3B	0.6841	0.5955	0.7945	0.054*
C5	0.3074 (3)	0.18707 (16)	0.62368 (16)	0.0395 (4)
C21	0.4623 (4)	0.81754 (18)	0.8788 (2)	0.0564 (5)
H21B	0.3424	0.8631	0.9139	0.068*
H21C	0.5249	0.8749	0.8361	0.068*
H21A	0.5801	0.8099	0.9490	0.068*
C71	−0.0632 (4)	0.08142 (19)	0.8275 (2)	0.0560 (5)
H71A	−0.1826	0.1269	0.8632	0.067*
H71B	0.0599	0.0796	0.8979	0.067*
H71C	−0.1217	−0.0163	0.7691	0.067*
C22	0.1742 (4)	0.6800 (2)	0.6694 (2)	0.0561 (5)
H22A	0.1123	0.5852	0.6057	0.067*
H22B	0.2343	0.7388	0.6271	0.067*
H22C	0.0558	0.7248	0.7068	0.067*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0415 (8)	0.0302 (7)	0.0400 (8)	0.0019 (6)	0.0160 (6)	0.0036 (6)
C8	0.0461 (9)	0.0315 (7)	0.0408 (8)	−0.0001 (6)	0.0182 (7)	0.0058 (6)
C4'	0.0357 (7)	0.0312 (7)	0.0358 (7)	0.0046 (6)	0.0125 (6)	0.0058 (6)
C8'	0.0360 (7)	0.0285 (7)	0.0343 (7)	0.0028 (5)	0.0128 (6)	0.0041 (6)
C2	0.0481 (9)	0.0282 (7)	0.0397 (8)	−0.0012 (6)	0.0125 (7)	0.0055 (6)
O1	0.0998 (11)	0.0415 (7)	0.0467 (7)	−0.0078 (7)	0.0398 (7)	−0.0023 (6)
C6	0.0474 (9)	0.0288 (7)	0.0563 (10)	0.0079 (6)	0.0156 (8)	0.0098 (7)
O2	0.0605 (8)	0.0436 (7)	0.0462 (7)	0.0007 (6)	0.0195 (6)	−0.0030 (5)
C7	0.0411 (8)	0.0308 (7)	0.0462 (9)	0.0025 (6)	0.0134 (7)	0.0088 (6)
O3	0.0437 (6)	0.0354 (6)	0.0546 (7)	0.0021 (5)	0.0047 (5)	0.0054 (5)
C4	0.0504 (9)	0.0403 (8)	0.0427 (9)	0.0061 (7)	0.0235 (7)	0.0096 (7)
C3	0.0470 (9)	0.0412 (9)	0.0465 (9)	−0.0006 (7)	0.0191 (7)	0.0128 (7)
C5	0.0357 (8)	0.0330 (7)	0.0449 (9)	0.0080 (6)	0.0119 (6)	0.0056 (6)
C21	0.0707 (12)	0.0332 (8)	0.0575 (11)	−0.0074 (8)	0.0190 (9)	0.0061 (8)
C71	0.0612 (12)	0.0411 (9)	0.0677 (12)	−0.0022 (8)	0.0234 (9)	0.0183 (9)
C22	0.0631 (12)	0.0434 (9)	0.0597 (11)	0.0085 (8)	0.0097 (9)	0.0188 (8)

Geometric parameters (Å, º)

C1—O1	1.2115 (19)	O2—C5	1.214 (2)
C1—C8'	1.5222 (19)	C7—O3	1.429 (2)
C1—C2	1.528 (2)	C7—C71	1.522 (2)
C8—C8'	1.522 (2)	O3—H3	0.8200
C8—C7	1.528 (2)	C4—C3	1.524 (2)
C8—H8A	0.9700	C4—H4A	0.9700
C8—H8B	0.9700	C4—H4B	0.9700
C4'—C4	1.514 (2)	C3—H3A	0.9700
C4'—C5	1.515 (2)	C3—H3B	0.9700
C4'—C8'	1.551 (2)	C21—H21B	0.9600
C4'—H4'	0.9800	C21—H21C	0.9600
C8'—H8'	0.9800	C21—H21A	0.9600
C2—C21	1.528 (2)	C71—H71A	0.9600
C2—C22	1.533 (3)	C71—H71B	0.9600
C2—C3	1.540 (2)	C71—H71C	0.9600
C6—C5	1.500 (2)	C22—H22A	0.9600
C6—C7	1.542 (2)	C22—H22B	0.9600
C6—H6A	0.9700	C22—H22C	0.9600
C6—H6B	0.9700
O1—C1—C8'	121.32 (14)	C71—C7—C6	111.09 (14)
O1—C1—C2	122.12 (14)	C8—C7—C6	109.90 (13)
C8'—C1—C2	116.48 (12)	C7—O3—H3	109.5
C8'—C8—C7	111.47 (12)	C4'—C4—C3	110.79 (12)
C8'—C8—H8A	109.3	C4'—C4—H4A	109.5
C7—C8—H8A	109.3	C3—C4—H4A	109.5
C8'—C8—H8B	109.3	C4'—C4—H4B	109.5
C7—C8—H8B	109.3	C3—C4—H4B	109.5
H8A—C8—H8B	108.0	H4A—C4—H4B	108.1
C4—C4'—C5	114.00 (12)	C4—C3—C2	113.71 (13)
C4—C4'—C8'	112.03 (13)	C4—C3—H3A	108.8
C5—C4'—C8'	107.69 (12)	C2—C3—H3A	108.8
C4—C4'—H4'	107.6	C4—C3—H3B	108.8
C5—C4'—H4'	107.6	C2—C3—H3B	108.8
C8'—C4'—H4'	107.6	H3A—C3—H3B	107.7
C8—C8'—C1	112.79 (12)	O2—C5—C6	122.73 (14)
C8—C8'—C4'	111.72 (12)	O2—C5—C4'	122.31 (15)
C1—C8'—C4'	108.38 (12)	C6—C5—C4'	114.95 (13)
C8—C8'—H8'	107.9	C2—C21—H21B	109.5
C1—C8'—H8'	107.9	C2—C21—H21C	109.5
C4'—C8'—H8'	107.9	H21B—C21—H21C	109.5
C1—C2—C21	110.11 (13)	C2—C21—H21A	109.5
C1—C2—C22	109.98 (14)	H21B—C21—H21A	109.5
C21—C2—C22	108.60 (15)	H21C—C21—H21A	109.5
C1—C2—C3	107.03 (13)	C7—C71—H71A	109.5
C21—C2—C3	110.11 (14)	C7—C71—H71B	109.5
C22—C2—C3	111.01 (15)	H71A—C71—H71B	109.5
C5—C6—C7	110.42 (13)	C7—C71—H71C	109.5
C5—C6—H6A	109.6	H71A—C71—H71C	109.5
C7—C6—H6A	109.6	H71B—C71—H71C	109.5
C5—C6—H6B	109.6	C2—C22—H22A	109.5
C7—C6—H6B	109.6	C2—C22—H22B	109.5
H6A—C6—H6B	108.1	H22A—C22—H22B	109.5
O3—C7—C71	109.78 (14)	C2—C22—H22C	109.5
O3—C7—C8	105.68 (12)	H22A—C22—H22C	109.5
C71—C7—C8	111.39 (14)	H22B—C22—H22C	109.5
O3—C7—C6	108.83 (14)
C7—C8—C8'—C1	179.86 (13)	C8'—C8—C7—C71	179.74 (14)
C7—C8—C8'—C4'	−57.76 (17)	C8'—C8—C7—C6	56.18 (18)
O1—C1—C8'—C8	2.7 (2)	C5—C6—C7—O3	60.85 (16)
C2—C1—C8'—C8	179.50 (13)	C5—C6—C7—C71	−178.17 (14)
O1—C1—C8'—C4'	−121.50 (18)	C5—C6—C7—C8	−54.43 (18)
C2—C1—C8'—C4'	55.28 (18)	C5—C4'—C4—C3	178.55 (13)
C4—C4'—C8'—C8	−178.79 (12)	C8'—C4'—C4—C3	55.94 (18)
C5—C4'—C8'—C8	55.08 (16)	C4'—C4—C3—C2	−56.8 (2)
C4—C4'—C8'—C1	−53.93 (17)	C1—C2—C3—C4	53.57 (18)
C5—C4'—C8'—C1	179.94 (12)	C21—C2—C3—C4	173.24 (14)
O1—C1—C2—C21	2.6 (2)	C22—C2—C3—C4	−66.46 (19)
C8'—C1—C2—C21	−174.15 (14)	C7—C6—C5—O2	−121.77 (17)
O1—C1—C2—C22	−117.05 (19)	C7—C6—C5—C4'	56.76 (18)
C8'—C1—C2—C22	66.21 (18)	C4—C4'—C5—O2	−2.3 (2)
O1—C1—C2—C3	122.27 (18)	C8'—C4'—C5—O2	122.70 (16)
C8'—C1—C2—C3	−54.48 (18)	C4—C4'—C5—C6	179.20 (13)
C8'—C8—C7—O3	−61.08 (16)	C8'—C4'—C5—C6	−55.84 (17)