Download citation
link to html
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.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804017313/hg6072sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804017313/hg6072Isup2.hkl
Contains datablock I

CCDC reference: 248857

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

checkCIF/PLATON results

No syntax errors found


No errors found in this datablock

Computing details top

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 top
Crystal data top
C13H20O3Z = 2
Mr = 224.29F(000) = 244
Triclinic, P1Dx = 1.235 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71069 Å
a = 6.0562 (13) ÅCell parameters from 25 reflections
b = 9.827 (2) Åθ = 35.0–47.5°
c = 11.1075 (16) ŵ = 0.09 mm1
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) Å3
Data collection top
Rigaku AFC-7S
diffractometer
1951 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.030
Graphite monochromatorθmax = 27.5°, θmin = 2.0°
θ/2θ scansh = 77
Absorption correction: ψ scan
(MSC/AFC Diffractometer Control Software; Molecular Structure Corporation, 1993)
k = 212
Tmin = 0.965, Tmax = 0.991l = 1414
3565 measured reflections3 standard reflections every 150 reflections
2768 independent reflections intensity decay: 2.5%
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.051H-atom parameters constrained
wR(F2) = 0.167 w = 1/[σ2(Fo2) + (0.0851P)2 + 0.1359P]
where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max < 0.001
2768 reflectionsΔρmax = 0.39 e Å3
149 parametersΔρmin = 0.20 e Å3
0 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.055 (11)
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
xyzUiso*/Ueq
C10.2727 (3)0.57127 (16)0.84623 (15)0.0386 (4)
C80.1039 (3)0.32632 (16)0.83823 (16)0.0402 (4)
H8A0.02200.36970.87020.048*
H8B0.22460.33140.91400.048*
C4'0.3906 (3)0.34550 (15)0.70635 (14)0.0352 (3)
H4'0.51500.34860.78090.042*
C8'0.1918 (3)0.41197 (15)0.76269 (14)0.0341 (3)
H8'0.06600.40780.68840.041*
C20.3659 (3)0.66562 (16)0.77882 (15)0.0403 (4)
O10.2723 (3)0.61833 (14)0.96167 (13)0.0643 (5)
C60.2187 (3)0.09874 (16)0.69435 (18)0.0450 (4)
H6A0.34160.09420.76510.054*
H6B0.16310.00030.63360.054*
O20.3083 (2)0.13662 (13)0.50821 (12)0.0541 (4)
C70.0236 (3)0.16708 (16)0.75157 (16)0.0402 (4)
O30.1584 (2)0.16920 (12)0.64581 (12)0.0486 (3)
H30.20730.08560.59590.058*
C40.4823 (3)0.43198 (17)0.63352 (16)0.0437 (4)
H4A0.36490.42660.55630.052*
H4B0.61140.39030.60420.052*
C30.5567 (3)0.59060 (18)0.72207 (17)0.0446 (4)
H3A0.60990.64360.67190.054*
H3B0.68410.59550.79450.054*
C50.3074 (3)0.18707 (16)0.62368 (16)0.0395 (4)
C210.4623 (4)0.81754 (18)0.8788 (2)0.0564 (5)
H21B0.34240.86310.91390.068*
H21C0.52490.87490.83610.068*
H21A0.58010.80990.94900.068*
C710.0632 (4)0.08142 (19)0.8275 (2)0.0560 (5)
H71A0.18260.12690.86320.067*
H71B0.05990.07960.89790.067*
H71C0.12170.01630.76910.067*
C220.1742 (4)0.6800 (2)0.6694 (2)0.0561 (5)
H22A0.11230.58520.60570.067*
H22B0.23430.73880.62710.067*
H22C0.05580.72480.70680.067*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0415 (8)0.0302 (7)0.0400 (8)0.0019 (6)0.0160 (6)0.0036 (6)
C80.0461 (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)
C20.0481 (9)0.0282 (7)0.0397 (8)0.0012 (6)0.0125 (7)0.0055 (6)
O10.0998 (11)0.0415 (7)0.0467 (7)0.0078 (7)0.0398 (7)0.0023 (6)
C60.0474 (9)0.0288 (7)0.0563 (10)0.0079 (6)0.0156 (8)0.0098 (7)
O20.0605 (8)0.0436 (7)0.0462 (7)0.0007 (6)0.0195 (6)0.0030 (5)
C70.0411 (8)0.0308 (7)0.0462 (9)0.0025 (6)0.0134 (7)0.0088 (6)
O30.0437 (6)0.0354 (6)0.0546 (7)0.0021 (5)0.0047 (5)0.0054 (5)
C40.0504 (9)0.0403 (8)0.0427 (9)0.0061 (7)0.0235 (7)0.0096 (7)
C30.0470 (9)0.0412 (9)0.0465 (9)0.0006 (7)0.0191 (7)0.0128 (7)
C50.0357 (8)0.0330 (7)0.0449 (9)0.0080 (6)0.0119 (6)0.0056 (6)
C210.0707 (12)0.0332 (8)0.0575 (11)0.0074 (8)0.0190 (9)0.0061 (8)
C710.0612 (12)0.0411 (9)0.0677 (12)0.0022 (8)0.0234 (9)0.0183 (9)
C220.0631 (12)0.0434 (9)0.0597 (11)0.0085 (8)0.0097 (9)0.0188 (8)
Geometric parameters (Å, º) top
C1—O11.2115 (19)O2—C51.214 (2)
C1—C8'1.5222 (19)C7—O31.429 (2)
C1—C21.528 (2)C7—C711.522 (2)
C8—C8'1.522 (2)O3—H30.8200
C8—C71.528 (2)C4—C31.524 (2)
C8—H8A0.9700C4—H4A0.9700
C8—H8B0.9700C4—H4B0.9700
C4'—C41.514 (2)C3—H3A0.9700
C4'—C51.515 (2)C3—H3B0.9700
C4'—C8'1.551 (2)C21—H21B0.9600
C4'—H4'0.9800C21—H21C0.9600
C8'—H8'0.9800C21—H21A0.9600
C2—C211.528 (2)C71—H71A0.9600
C2—C221.533 (3)C71—H71B0.9600
C2—C31.540 (2)C71—H71C0.9600
C6—C51.500 (2)C22—H22A0.9600
C6—C71.542 (2)C22—H22B0.9600
C6—H6A0.9700C22—H22C0.9600
C6—H6B0.9700
O1—C1—C8'121.32 (14)C71—C7—C6111.09 (14)
O1—C1—C2122.12 (14)C8—C7—C6109.90 (13)
C8'—C1—C2116.48 (12)C7—O3—H3109.5
C8'—C8—C7111.47 (12)C4'—C4—C3110.79 (12)
C8'—C8—H8A109.3C4'—C4—H4A109.5
C7—C8—H8A109.3C3—C4—H4A109.5
C8'—C8—H8B109.3C4'—C4—H4B109.5
C7—C8—H8B109.3C3—C4—H4B109.5
H8A—C8—H8B108.0H4A—C4—H4B108.1
C4—C4'—C5114.00 (12)C4—C3—C2113.71 (13)
C4—C4'—C8'112.03 (13)C4—C3—H3A108.8
C5—C4'—C8'107.69 (12)C2—C3—H3A108.8
C4—C4'—H4'107.6C4—C3—H3B108.8
C5—C4'—H4'107.6C2—C3—H3B108.8
C8'—C4'—H4'107.6H3A—C3—H3B107.7
C8—C8'—C1112.79 (12)O2—C5—C6122.73 (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'—H8'107.9C2—C21—H21B109.5
C1—C8'—H8'107.9C2—C21—H21C109.5
C4'—C8'—H8'107.9H21B—C21—H21C109.5
C1—C2—C21110.11 (13)C2—C21—H21A109.5
C1—C2—C22109.98 (14)H21B—C21—H21A109.5
C21—C2—C22108.60 (15)H21C—C21—H21A109.5
C1—C2—C3107.03 (13)C7—C71—H71A109.5
C21—C2—C3110.11 (14)C7—C71—H71B109.5
C22—C2—C3111.01 (15)H71A—C71—H71B109.5
C5—C6—C7110.42 (13)C7—C71—H71C109.5
C5—C6—H6A109.6H71A—C71—H71C109.5
C7—C6—H6A109.6H71B—C71—H71C109.5
C5—C6—H6B109.6C2—C22—H22A109.5
C7—C6—H6B109.6C2—C22—H22B109.5
H6A—C6—H6B108.1H22A—C22—H22B109.5
O3—C7—C71109.78 (14)C2—C22—H22C109.5
O3—C7—C8105.68 (12)H22A—C22—H22C109.5
C71—C7—C8111.39 (14)H22B—C22—H22C109.5
O3—C7—C6108.83 (14)
C7—C8—C8'—C1179.86 (13)C8'—C8—C7—C71179.74 (14)
C7—C8—C8'—C4'57.76 (17)C8'—C8—C7—C656.18 (18)
O1—C1—C8'—C82.7 (2)C5—C6—C7—O360.85 (16)
C2—C1—C8'—C8179.50 (13)C5—C6—C7—C71178.17 (14)
O1—C1—C8'—C4'121.50 (18)C5—C6—C7—C854.43 (18)
C2—C1—C8'—C4'55.28 (18)C5—C4'—C4—C3178.55 (13)
C4—C4'—C8'—C8178.79 (12)C8'—C4'—C4—C355.94 (18)
C5—C4'—C8'—C855.08 (16)C4'—C4—C3—C256.8 (2)
C4—C4'—C8'—C153.93 (17)C1—C2—C3—C453.57 (18)
C5—C4'—C8'—C1179.94 (12)C21—C2—C3—C4173.24 (14)
O1—C1—C2—C212.6 (2)C22—C2—C3—C466.46 (19)
C8'—C1—C2—C21174.15 (14)C7—C6—C5—O2121.77 (17)
O1—C1—C2—C22117.05 (19)C7—C6—C5—C4'56.76 (18)
C8'—C1—C2—C2266.21 (18)C4—C4'—C5—O22.3 (2)
O1—C1—C2—C3122.27 (18)C8'—C4'—C5—O2122.70 (16)
C8'—C1—C2—C354.48 (18)C4—C4'—C5—C6179.20 (13)
C8'—C8—C7—O361.08 (16)C8'—C4'—C5—C655.84 (17)
 

Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds