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The crystal structure of the title ester, C16H26O4, consists of discrete spiro­cyclic mol­ecules. The six-membered 1,3-dioxane fragment is in a chair conformation and the cyclo­hexene fragment is in a distorted half-chair conformation. In the crystal structure, the mol­ecules are connected by weak C—H...O contacts, with C...O distances ranging from 2.642 (1) to 2.762 (1) Å, forming a three-dimensional network.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805013127/su6192sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805013127/su6192Isup2.hkl
Contains datablock I

CCDC reference: 274645

Key indicators

  • Single-crystal X-ray study
  • T = 150 K
  • Mean [sigma](C-C)= 0.002 Å
  • R factor = 0.038
  • wR factor = 0.120
  • Data-to-parameter ratio = 16.8

checkCIF/PLATON results

No syntax errors found


No errors found in this datablock

Computing details top

Data collection: COLLECT (Nonius, 1998); cell refinement: DENZO–SMN (Otwinowski & Minor, 1997); data reduction: DENZO–SMN; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: DIAMOND (Brandenburg & Berndt, 1999); software used to prepare material for publication: WinGX (Farrugia, 1999).

Methyl 3,3,7,7,9-pentamethyl-1,5-dioxaspiro[5.5]undec-8-ene-8-carboxylate top
Crystal data top
C16H26O4F(000) = 616
Mr = 282.37Dx = 1.165 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 2855 reflections
a = 10.735 (2) Åθ = 2.5–26.0°
b = 9.4311 (19) ŵ = 0.08 mm1
c = 16.610 (3) ÅT = 150 K
β = 106.81 (3)°Block, colourless
V = 1609.7 (6) Å30.20 × 0.20 × 0.15 mm
Z = 4
Data collection top
Bruker–Nonius KappaCCD
diffractometer
2855 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.039
Graphite monochromatorθmax = 26.0°, θmin = 2.5°
φ scans, and ω scans with κ offsetsh = 1313
20225 measured reflectionsk = 1111
3133 independent reflectionsl = 2020
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.038Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.120H-atom parameters constrained
S = 1.08 w = 1/[σ2(Fo2) + (0.0656P)2 + 0.4495P]
where P = (Fo2 + 2Fc2)/3
3133 reflections(Δ/σ)max = 0.001
187 parametersΔρmax = 0.28 e Å3
0 restraintsΔρmin = 0.23 e Å3
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
O10.75398 (9)0.64300 (9)0.38230 (6)0.0318 (2)
O20.65704 (9)0.53065 (10)0.26149 (6)0.0343 (3)
O30.78460 (8)0.26792 (9)0.54633 (5)0.0243 (2)
O40.64592 (8)0.08847 (9)0.47386 (5)0.0231 (2)
C10.70798 (16)0.77650 (14)0.34138 (10)0.0404 (4)
H1A0.76590.80740.30880.061*
H1B0.70720.84810.38400.061*
H1C0.61970.76430.30370.061*
C20.72235 (11)0.52694 (13)0.33423 (8)0.0239 (3)
C30.77542 (11)0.39450 (12)0.38163 (7)0.0217 (3)
C40.67248 (11)0.29951 (12)0.40178 (7)0.0219 (3)
C50.59425 (12)0.22202 (14)0.32131 (8)0.0312 (3)
H5A0.55770.29160.27700.047*
H5B0.52350.16790.33300.047*
H5C0.65180.15720.30270.047*
C60.57748 (13)0.39025 (14)0.43399 (9)0.0316 (3)
H6A0.62670.44890.48120.047*
H6B0.51820.32800.45270.047*
H6C0.52710.45150.38850.047*
C70.74177 (11)0.19090 (12)0.46971 (7)0.0209 (3)
C80.85623 (11)0.12211 (13)0.44741 (8)0.0256 (3)
H8A0.89530.04820.48950.031*
H8B0.82490.07590.39170.031*
C90.95908 (11)0.23240 (13)0.44555 (8)0.0281 (3)
H9A1.00890.25630.50400.034*
H9B1.02060.19090.41770.034*
C100.90256 (11)0.36605 (13)0.40030 (7)0.0241 (3)
C111.00054 (13)0.46181 (15)0.37849 (9)0.0325 (3)
H11A0.95710.54850.35200.049*
H11B1.03910.41270.33950.049*
H11C1.06910.48650.42990.049*
C120.83243 (12)0.18101 (15)0.61941 (8)0.0294 (3)
H12A0.85740.24190.67010.035*
H12B0.91110.12970.61580.035*
C130.72977 (12)0.07400 (14)0.62756 (8)0.0285 (3)
C140.61380 (14)0.15036 (16)0.64377 (9)0.0349 (3)
H14A0.57980.22090.59950.052*
H14B0.64170.19780.69850.052*
H14C0.54550.08130.64360.052*
C150.78986 (15)0.03074 (18)0.69863 (9)0.0420 (4)
H15A0.72670.10550.69920.063*
H15B0.81320.01940.75260.063*
H15C0.86810.07310.68960.063*
C160.68573 (12)0.00627 (13)0.54427 (8)0.0258 (3)
H16A0.75810.06630.53820.031*
H16B0.61220.06940.54470.031*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0421 (5)0.0206 (4)0.0311 (5)0.0015 (4)0.0081 (4)0.0003 (3)
O20.0435 (6)0.0294 (5)0.0252 (5)0.0021 (4)0.0026 (4)0.0037 (4)
O30.0248 (4)0.0258 (4)0.0196 (4)0.0048 (3)0.0022 (3)0.0005 (3)
O40.0213 (4)0.0226 (4)0.0231 (4)0.0046 (3)0.0027 (3)0.0031 (3)
C10.0582 (9)0.0212 (7)0.0458 (8)0.0058 (6)0.0212 (7)0.0034 (6)
C20.0240 (6)0.0234 (6)0.0255 (6)0.0014 (5)0.0090 (5)0.0004 (5)
C30.0234 (6)0.0212 (6)0.0197 (5)0.0027 (4)0.0048 (4)0.0008 (4)
C40.0190 (5)0.0224 (6)0.0232 (6)0.0007 (4)0.0040 (4)0.0022 (5)
C50.0286 (6)0.0335 (7)0.0255 (6)0.0092 (5)0.0015 (5)0.0043 (5)
C60.0267 (6)0.0323 (7)0.0385 (7)0.0075 (5)0.0137 (5)0.0093 (6)
C70.0191 (5)0.0210 (6)0.0210 (6)0.0035 (4)0.0033 (4)0.0002 (4)
C80.0234 (6)0.0236 (6)0.0298 (6)0.0025 (5)0.0076 (5)0.0032 (5)
C90.0199 (6)0.0308 (7)0.0337 (7)0.0025 (5)0.0080 (5)0.0043 (5)
C100.0233 (6)0.0252 (6)0.0238 (6)0.0030 (5)0.0067 (5)0.0013 (5)
C110.0269 (6)0.0341 (7)0.0376 (7)0.0063 (5)0.0111 (5)0.0027 (6)
C120.0255 (6)0.0376 (7)0.0210 (6)0.0065 (5)0.0003 (5)0.0037 (5)
C130.0262 (6)0.0338 (7)0.0233 (6)0.0040 (5)0.0037 (5)0.0056 (5)
C140.0352 (7)0.0402 (8)0.0319 (7)0.0065 (6)0.0140 (6)0.0030 (6)
C150.0367 (8)0.0529 (9)0.0316 (8)0.0051 (7)0.0022 (6)0.0168 (7)
C160.0245 (6)0.0249 (6)0.0264 (6)0.0011 (5)0.0048 (5)0.0061 (5)
Geometric parameters (Å, º) top
O1—C21.3394 (15)C8—H8A0.9900
O1—C11.4481 (16)C8—H8B0.9900
O2—C21.2094 (16)C9—C101.5026 (17)
O3—C71.4214 (14)C9—H9A0.9900
O3—C121.4311 (15)C9—H9B0.9900
O4—C71.4275 (13)C10—C111.5078 (17)
O4—C161.4352 (14)C11—H11A0.9800
C1—H1A0.9800C11—H11B0.9800
C1—H1B0.9800C11—H11C0.9800
C1—H1C0.9800C12—C131.5290 (17)
C2—C31.4984 (17)C12—H12A0.9900
C3—C101.3364 (17)C12—H12B0.9900
C3—C41.5328 (15)C13—C161.5271 (18)
C4—C51.5416 (17)C13—C141.5279 (19)
C4—C61.5409 (17)C13—C151.5312 (18)
C4—C71.5460 (16)C14—H14A0.9800
C5—H5A0.9800C14—H14B0.9800
C5—H5B0.9800C14—H14C0.9800
C5—H5C0.9800C15—H15A0.9800
C6—H6A0.9800C15—H15B0.9800
C6—H6B0.9800C15—H15C0.9800
C6—H6C0.9800C16—H16A0.9900
C7—C81.5268 (16)C16—H16B0.9900
C8—C91.5237 (17)
C2—O1—C1115.94 (10)C10—C9—C8113.12 (10)
C7—O3—C12114.24 (9)C10—C9—H9A109.0
C7—O4—C16114.31 (9)C8—C9—H9A109.0
O1—C1—H1A109.5C10—C9—H9B109.0
O1—C1—H1B109.5C8—C9—H9B109.0
H1A—C1—H1B109.5H9A—C9—H9B107.8
O1—C1—H1C109.5C3—C10—C9121.46 (11)
H1A—C1—H1C109.5C3—C10—C11124.09 (11)
H1B—C1—H1C109.5C9—C10—C11114.44 (10)
O2—C2—O1123.07 (12)C10—C11—H11A109.5
O2—C2—C3124.85 (11)C10—C11—H11B109.5
O1—C2—C3112.07 (10)H11A—C11—H11B109.5
C10—C3—C2119.79 (11)C10—C11—H11C109.5
C10—C3—C4125.76 (11)H11A—C11—H11C109.5
C2—C3—C4114.42 (10)H11B—C11—H11C109.5
C3—C4—C5109.52 (10)O3—C12—C13111.23 (10)
C3—C4—C6110.03 (10)O3—C12—H12A109.4
C5—C4—C6108.36 (10)C13—C12—H12A109.4
C3—C4—C7108.75 (9)O3—C12—H12B109.4
C5—C4—C7110.19 (10)C13—C12—H12B109.4
C6—C4—C7109.97 (10)H12A—C12—H12B108.0
C4—C5—H5A109.5C16—C13—C14109.80 (10)
C4—C5—H5B109.5C16—C13—C12106.81 (10)
H5A—C5—H5B109.5C14—C13—C12110.44 (11)
C4—C5—H5C109.5C16—C13—C15109.25 (12)
H5A—C5—H5C109.5C14—C13—C15110.57 (11)
H5B—C5—H5C109.5C12—C13—C15109.90 (10)
C4—C6—H6A109.5C13—C14—H14A109.5
C4—C6—H6B109.5C13—C14—H14B109.5
H6A—C6—H6B109.5H14A—C14—H14B109.5
C4—C6—H6C109.5C13—C14—H14C109.5
H6A—C6—H6C109.5H14A—C14—H14C109.5
H6B—C6—H6C109.5H14B—C14—H14C109.5
O3—C7—O4110.71 (9)C13—C15—H15A109.5
O3—C7—C8111.09 (9)C13—C15—H15B109.5
O4—C7—C8111.47 (9)H15A—C15—H15B109.5
O3—C7—C4106.12 (9)C13—C15—H15C109.5
O4—C7—C4106.39 (9)H15A—C15—H15C109.5
C8—C7—C4110.83 (9)H15B—C15—H15C109.5
C9—C8—C7110.70 (10)O4—C16—C13111.77 (10)
C9—C8—H8A109.5O4—C16—H16A109.3
C7—C8—H8A109.5C13—C16—H16A109.3
C9—C8—H8B109.5O4—C16—H16B109.3
C7—C8—H8B109.5C13—C16—H16B109.3
H8A—C8—H8B108.1H16A—C16—H16B107.9
C1—O1—C2—O21.58 (17)C6—C4—C7—O470.83 (11)
C1—O1—C2—C3179.32 (11)C3—C4—C7—C847.28 (12)
O2—C2—C3—C10107.29 (15)C5—C4—C7—C872.78 (12)
O1—C2—C3—C1073.63 (14)C6—C4—C7—C8167.83 (10)
O2—C2—C3—C470.66 (15)O3—C7—C8—C954.53 (13)
O1—C2—C3—C4108.42 (11)O4—C7—C8—C9178.51 (9)
C10—C3—C4—C5103.18 (14)C4—C7—C8—C963.19 (12)
C2—C3—C4—C574.63 (13)C7—C8—C9—C1044.76 (14)
C10—C3—C4—C6137.80 (12)C2—C3—C10—C9178.22 (11)
C2—C3—C4—C644.39 (13)C4—C3—C10—C90.52 (19)
C10—C3—C4—C717.29 (16)C2—C3—C10—C111.60 (18)
C2—C3—C4—C7164.90 (10)C4—C3—C10—C11179.31 (11)
C12—O3—C7—O455.20 (12)C8—C9—C10—C314.17 (17)
C12—O3—C7—C869.22 (12)C8—C9—C10—C11165.66 (11)
C12—O3—C7—C4170.24 (9)C7—O3—C12—C1357.12 (13)
C16—O4—C7—O354.08 (12)O3—C12—C13—C1653.54 (14)
C16—O4—C7—C870.12 (12)O3—C12—C13—C1465.82 (13)
C16—O4—C7—C4168.96 (9)O3—C12—C13—C15171.93 (11)
C3—C4—C7—O373.43 (11)C7—O4—C16—C1355.20 (13)
C5—C4—C7—O3166.51 (9)C14—C13—C16—O467.01 (13)
C6—C4—C7—O347.12 (12)C12—C13—C16—O452.76 (13)
C3—C4—C7—O4168.62 (9)C15—C13—C16—O4171.58 (10)
C5—C4—C7—O448.56 (12)
 

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