Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680300864X/na6225sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S160053680300864X/na6225Isup2.hkl |
CCDC reference: 214633
Key indicators
- Single-crystal X-ray study
- T = 150 K
- Mean (C-C) = 0.003 Å
- R factor = 0.040
- wR factor = 0.100
- Data-to-parameter ratio = 14.7
checkCIF results
No syntax errors found ADDSYM reports no extra symmetry
The title lactone was formed by oxidation of the analogous lactol using pyridinium dichromate and recrystallized from dichloromethane solution by evaporation. The synthesis of the compound has been reported elsewhere (Page et al., 2003).
H atoms were inserted at calculated positions,the constrained C—H distances were 0.95, 0.98, 0.99 and 1.00 Å for H atoms bonded to sp2, methylene, methyl and tertiary C atoms, respectively. H atoms were refined with Uiso(H) = 1.2Ueq(C), except for the methyl groups where Uiso(H) = 1.5Ueq(C).
Data collection: SMART (Bruker, 1998); cell refinement: SMART; data reduction: SAINT (Bruker, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Sheldrick, 1998); software used to prepare material for publication: SHELXTL.
C11H16O2 | F(000) = 784 |
Mr = 180.24 | Dx = 1.201 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 14.2924 (17) Å | Cell parameters from 3712 reflections |
b = 5.4060 (6) Å | θ = 2.6–27.8° |
c = 25.969 (3) Å | µ = 0.08 mm−1 |
β = 96.530 (2)° | T = 150 K |
V = 1993.4 (4) Å3 | Lath, colourless |
Z = 8 | 0.48 × 0.11 × 0.03 mm |
Bruker SMART CCD area-detector diffractometer | 3517 independent reflections |
Radiation source: fine-focus sealed tube | 2526 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.031 |
ϕ and ω scans | θmax = 25.0°, θmin = 1.6° |
Absorption correction: multi-scan (SHELXTL/SADABS; Sheldrick, 1997) | h = −16→16 |
Tmin = 0.938, Tmax = 1.000 | k = −6→6 |
13507 measured reflections | l = −30→30 |
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)] = 0.040 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.100 | H-atom parameters constrained |
S = 1.04 | w = 1/[σ2(Fo2) + (0.0381P)2 + 0.7308P] where P = (Fo2 + 2Fc2)/3 |
3517 reflections | (Δ/σ)max < 0.001 |
239 parameters | Δρmax = 0.21 e Å−3 |
0 restraints | Δρmin = −0.17 e Å−3 |
C11H16O2 | V = 1993.4 (4) Å3 |
Mr = 180.24 | Z = 8 |
Monoclinic, P21/n | Mo Kα radiation |
a = 14.2924 (17) Å | µ = 0.08 mm−1 |
b = 5.4060 (6) Å | T = 150 K |
c = 25.969 (3) Å | 0.48 × 0.11 × 0.03 mm |
β = 96.530 (2)° |
Bruker SMART CCD area-detector diffractometer | 3517 independent reflections |
Absorption correction: multi-scan (SHELXTL/SADABS; Sheldrick, 1997) | 2526 reflections with I > 2σ(I) |
Tmin = 0.938, Tmax = 1.000 | Rint = 0.031 |
13507 measured reflections |
R[F2 > 2σ(F2)] = 0.040 | 0 restraints |
wR(F2) = 0.100 | H-atom parameters constrained |
S = 1.04 | Δρmax = 0.21 e Å−3 |
3517 reflections | Δρmin = −0.17 e Å−3 |
239 parameters |
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 | ||
O1A | 0.26121 (8) | 0.2602 (2) | 0.21417 (4) | 0.0303 (3) | |
O2A | 0.40313 (9) | 0.1752 (3) | 0.25015 (5) | 0.0406 (3) | |
C1A | 0.33935 (12) | 0.1198 (3) | 0.21740 (6) | 0.0285 (4) | |
C2A | 0.34965 (11) | −0.0874 (3) | 0.17930 (6) | 0.0268 (4) | |
H2A | 0.3736 | −0.2355 | 0.1998 | 0.032* | |
C3A | 0.42592 (12) | −0.0111 (4) | 0.14539 (6) | 0.0311 (4) | |
H3A1 | 0.4028 | 0.1295 | 0.1230 | 0.037* | |
H3A2 | 0.4827 | 0.0444 | 0.1678 | 0.037* | |
C4A | 0.45203 (13) | −0.2255 (4) | 0.11148 (7) | 0.0363 (5) | |
H4A | 0.4823 | −0.3569 | 0.1349 | 0.044* | |
C5A | 0.52468 (14) | −0.1378 (5) | 0.07641 (8) | 0.0546 (6) | |
H5A1 | 0.5495 | −0.2807 | 0.0591 | 0.082* | |
H5A2 | 0.5764 | −0.0530 | 0.0974 | 0.082* | |
H5A3 | 0.4946 | −0.0236 | 0.0503 | 0.082* | |
C6A | 0.36383 (13) | −0.3350 (3) | 0.08202 (7) | 0.0317 (4) | |
C7A | 0.37482 (15) | −0.4811 (4) | 0.03342 (7) | 0.0483 (6) | |
H7A1 | 0.3145 | −0.5581 | 0.0207 | 0.072* | |
H7A2 | 0.4226 | −0.6099 | 0.0413 | 0.072* | |
H7A3 | 0.3945 | −0.3701 | 0.0068 | 0.072* | |
C8A | 0.28002 (13) | −0.3042 (3) | 0.09833 (7) | 0.0307 (4) | |
H8A | 0.2279 | −0.3774 | 0.0780 | 0.037* | |
C9A | 0.25927 (11) | −0.1652 (3) | 0.14574 (6) | 0.0258 (4) | |
H9A | 0.2240 | −0.2793 | 0.1669 | 0.031* | |
C10A | 0.19746 (12) | 0.0614 (3) | 0.13268 (6) | 0.0286 (4) | |
H10A | 0.2305 | 0.1800 | 0.1120 | 0.034* | |
H10B | 0.1381 | 0.0113 | 0.1119 | 0.034* | |
C11A | 0.17608 (12) | 0.1817 (3) | 0.18223 (7) | 0.0300 (4) | |
H11A | 0.1351 | 0.3272 | 0.1739 | 0.036* | |
H11B | 0.1413 | 0.0634 | 0.2021 | 0.036* | |
O1B | 0.78395 (8) | 0.3734 (2) | 0.22081 (5) | 0.0347 (3) | |
O2B | 0.65769 (9) | 0.3000 (3) | 0.16778 (6) | 0.0534 (4) | |
C1B | 0.73743 (13) | 0.2385 (4) | 0.18278 (7) | 0.0344 (4) | |
C2B | 0.78428 (12) | 0.0234 (3) | 0.15815 (6) | 0.0297 (4) | |
H2B | 0.7409 | −0.1216 | 0.1583 | 0.036* | |
C3B | 0.79203 (13) | 0.0876 (4) | 0.10130 (7) | 0.0344 (4) | |
H3B1 | 0.7295 | 0.1392 | 0.0844 | 0.041* | |
H3B2 | 0.8358 | 0.2286 | 0.0997 | 0.041* | |
C4B | 0.82724 (13) | −0.1306 (4) | 0.07172 (7) | 0.0344 (4) | |
H4B | 0.7776 | −0.2618 | 0.0697 | 0.041* | |
C5B | 0.83940 (16) | −0.0525 (4) | 0.01607 (7) | 0.0518 (6) | |
H5B1 | 0.8920 | 0.0642 | 0.0166 | 0.078* | |
H5B2 | 0.7815 | 0.0269 | 0.0003 | 0.078* | |
H5B3 | 0.8525 | −0.1988 | −0.0042 | 0.078* | |
C6B | 0.91601 (12) | −0.2381 (3) | 0.10077 (7) | 0.0299 (4) | |
C7B | 0.97949 (14) | −0.3923 (4) | 0.07076 (8) | 0.0428 (5) | |
H7B1 | 1.0293 | −0.4671 | 0.0949 | 0.064* | |
H7B2 | 1.0079 | −0.2867 | 0.0461 | 0.064* | |
H7B3 | 0.9424 | −0.5229 | 0.0519 | 0.064* | |
C8B | 0.93675 (12) | −0.2012 (3) | 0.15116 (7) | 0.0286 (4) | |
H8B | 0.9935 | −0.2733 | 0.1670 | 0.034* | |
C9B | 0.87945 (11) | −0.0567 (3) | 0.18600 (6) | 0.0261 (4) | |
H9B | 0.8667 | −0.1680 | 0.2152 | 0.031* | |
C10B | 0.93331 (12) | 0.1667 (3) | 0.20956 (6) | 0.0289 (4) | |
H10C | 0.9938 | 0.1123 | 0.2285 | 0.035* | |
H10D | 0.9473 | 0.2813 | 0.1817 | 0.035* | |
C11B | 0.87578 (12) | 0.2974 (4) | 0.24594 (7) | 0.0327 (4) | |
H11C | 0.8668 | 0.1863 | 0.2753 | 0.039* | |
H11D | 0.9105 | 0.4452 | 0.2601 | 0.039* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1A | 0.0311 (7) | 0.0306 (7) | 0.0295 (7) | 0.0018 (6) | 0.0041 (5) | −0.0051 (5) |
O2A | 0.0367 (7) | 0.0518 (9) | 0.0315 (7) | 0.0001 (7) | −0.0043 (6) | −0.0136 (6) |
C1A | 0.0311 (10) | 0.0318 (10) | 0.0229 (9) | −0.0009 (8) | 0.0043 (8) | 0.0006 (8) |
C2A | 0.0306 (9) | 0.0275 (9) | 0.0221 (9) | 0.0034 (8) | 0.0022 (7) | 0.0004 (8) |
C3A | 0.0278 (9) | 0.0402 (11) | 0.0251 (9) | −0.0005 (8) | 0.0024 (7) | −0.0033 (8) |
C4A | 0.0355 (10) | 0.0451 (12) | 0.0284 (10) | 0.0073 (9) | 0.0043 (8) | −0.0042 (9) |
C5A | 0.0412 (12) | 0.0769 (17) | 0.0490 (13) | −0.0049 (12) | 0.0191 (10) | −0.0215 (12) |
C6A | 0.0435 (11) | 0.0273 (10) | 0.0247 (9) | 0.0029 (8) | 0.0053 (8) | −0.0019 (8) |
C7A | 0.0627 (14) | 0.0448 (13) | 0.0391 (11) | −0.0001 (11) | 0.0133 (10) | −0.0145 (10) |
C8A | 0.0392 (11) | 0.0253 (9) | 0.0264 (9) | −0.0051 (8) | −0.0013 (8) | −0.0007 (8) |
C9A | 0.0291 (9) | 0.0242 (9) | 0.0243 (9) | −0.0036 (7) | 0.0033 (7) | 0.0018 (7) |
C10A | 0.0272 (9) | 0.0294 (10) | 0.0286 (9) | −0.0033 (8) | 0.0004 (7) | 0.0026 (8) |
C11A | 0.0259 (9) | 0.0288 (10) | 0.0356 (10) | 0.0007 (8) | 0.0042 (8) | 0.0004 (8) |
O1B | 0.0291 (7) | 0.0331 (7) | 0.0420 (7) | 0.0022 (6) | 0.0045 (6) | −0.0071 (6) |
O2B | 0.0308 (8) | 0.0587 (10) | 0.0688 (10) | 0.0103 (7) | −0.0030 (7) | −0.0138 (8) |
C1B | 0.0263 (10) | 0.0380 (11) | 0.0395 (11) | −0.0021 (9) | 0.0059 (8) | −0.0006 (9) |
C2B | 0.0265 (9) | 0.0310 (10) | 0.0319 (10) | −0.0050 (8) | 0.0045 (8) | −0.0005 (8) |
C3B | 0.0323 (10) | 0.0372 (11) | 0.0324 (10) | −0.0024 (9) | −0.0018 (8) | 0.0054 (9) |
C4B | 0.0379 (11) | 0.0389 (11) | 0.0258 (9) | −0.0103 (9) | 0.0018 (8) | −0.0001 (8) |
C5B | 0.0722 (15) | 0.0560 (14) | 0.0264 (10) | −0.0084 (12) | 0.0022 (10) | 0.0017 (10) |
C6B | 0.0329 (10) | 0.0285 (10) | 0.0297 (10) | −0.0072 (8) | 0.0085 (8) | −0.0029 (8) |
C7B | 0.0504 (12) | 0.0424 (12) | 0.0383 (11) | −0.0058 (10) | 0.0172 (9) | −0.0087 (10) |
C8B | 0.0288 (9) | 0.0263 (9) | 0.0310 (10) | −0.0001 (8) | 0.0050 (8) | 0.0010 (8) |
C9B | 0.0289 (9) | 0.0270 (9) | 0.0227 (9) | −0.0013 (8) | 0.0041 (7) | 0.0021 (7) |
C10B | 0.0269 (9) | 0.0307 (10) | 0.0285 (9) | −0.0007 (8) | 0.0009 (7) | 0.0000 (8) |
C11B | 0.0311 (10) | 0.0323 (10) | 0.0341 (10) | −0.0020 (8) | 0.0015 (8) | −0.0040 (8) |
O1A—C1A | 1.345 (2) | O1B—C1B | 1.342 (2) |
O1A—C11A | 1.456 (2) | O1B—C11B | 1.457 (2) |
O2A—C1A | 1.211 (2) | O2B—C1B | 1.208 (2) |
C1A—C2A | 1.513 (2) | C1B—C2B | 1.519 (3) |
C2A—C9A | 1.533 (2) | C2B—C9B | 1.529 (2) |
C2A—C3A | 1.534 (2) | C2B—C3B | 1.533 (2) |
C2A—H2A | 1.0000 | C2B—H2B | 1.0000 |
C3A—C4A | 1.528 (3) | C3B—C4B | 1.524 (3) |
C3A—H3A1 | 0.9900 | C3B—H3B1 | 0.9900 |
C3A—H3A2 | 0.9900 | C3B—H3B2 | 0.9900 |
C4A—C6A | 1.518 (3) | C4B—C6B | 1.516 (3) |
C4A—C5A | 1.532 (3) | C4B—C5B | 1.534 (2) |
C4A—H4A | 1.0000 | C4B—H4B | 1.0000 |
C5A—H5A1 | 0.9800 | C5B—H5B1 | 0.9800 |
C5A—H5A2 | 0.9800 | C5B—H5B2 | 0.9800 |
C5A—H5A3 | 0.9800 | C5B—H5B3 | 0.9800 |
C6A—C8A | 1.326 (2) | C6B—C8B | 1.324 (2) |
C6A—C7A | 1.512 (2) | C6B—C7B | 1.512 (3) |
C7A—H7A1 | 0.9800 | C7B—H7B1 | 0.9800 |
C7A—H7A2 | 0.9800 | C7B—H7B2 | 0.9800 |
C7A—H7A3 | 0.9800 | C7B—H7B3 | 0.9800 |
C8A—C9A | 1.500 (2) | C8B—C9B | 1.506 (2) |
C8A—H8A | 0.9500 | C8B—H8B | 0.9500 |
C9A—C10A | 1.526 (2) | C9B—C10B | 1.523 (2) |
C9A—H9A | 1.0000 | C9B—H9B | 1.0000 |
C10A—C11A | 1.504 (2) | C10B—C11B | 1.498 (2) |
C10A—H10A | 0.9900 | C10B—H10C | 0.9900 |
C10A—H10B | 0.9900 | C10B—H10D | 0.9900 |
C11A—H11A | 0.9900 | C11B—H11C | 0.9900 |
C11A—H11B | 0.9900 | C11B—H11D | 0.9900 |
C1A—O1A—C11A | 120.36 (13) | C1B—O1B—C11B | 121.46 (14) |
O2A—C1A—O1A | 117.23 (16) | O2B—C1B—O1B | 117.25 (17) |
O2A—C1A—C2A | 121.37 (16) | O2B—C1B—C2B | 121.31 (17) |
O1A—C1A—C2A | 121.26 (14) | O1B—C1B—C2B | 121.40 (15) |
C1A—C2A—C9A | 115.90 (14) | C1B—C2B—C9B | 115.38 (14) |
C1A—C2A—C3A | 107.74 (14) | C1B—C2B—C3B | 108.44 (15) |
C9A—C2A—C3A | 110.82 (13) | C9B—C2B—C3B | 111.22 (13) |
C1A—C2A—H2A | 107.3 | C1B—C2B—H2B | 107.1 |
C9A—C2A—H2A | 107.3 | C9B—C2B—H2B | 107.1 |
C3A—C2A—H2A | 107.3 | C3B—C2B—H2B | 107.1 |
C4A—C3A—C2A | 111.29 (15) | C4B—C3B—C2B | 111.99 (15) |
C4A—C3A—H3A1 | 109.4 | C4B—C3B—H3B1 | 109.2 |
C2A—C3A—H3A1 | 109.4 | C2B—C3B—H3B1 | 109.2 |
C4A—C3A—H3A2 | 109.4 | C4B—C3B—H3B2 | 109.2 |
C2A—C3A—H3A2 | 109.4 | C2B—C3B—H3B2 | 109.2 |
H3A1—C3A—H3A2 | 108.0 | H3B1—C3B—H3B2 | 107.9 |
C6A—C4A—C3A | 110.06 (14) | C6B—C4B—C3B | 110.58 (14) |
C6A—C4A—C5A | 113.64 (15) | C6B—C4B—C5B | 113.34 (16) |
C3A—C4A—C5A | 109.53 (17) | C3B—C4B—C5B | 109.93 (16) |
C6A—C4A—H4A | 107.8 | C6B—C4B—H4B | 107.6 |
C3A—C4A—H4A | 107.8 | C3B—C4B—H4B | 107.6 |
C5A—C4A—H4A | 107.8 | C5B—C4B—H4B | 107.6 |
C4A—C5A—H5A1 | 109.5 | C4B—C5B—H5B1 | 109.5 |
C4A—C5A—H5A2 | 109.5 | C4B—C5B—H5B2 | 109.5 |
H5A1—C5A—H5A2 | 109.5 | H5B1—C5B—H5B2 | 109.5 |
C4A—C5A—H5A3 | 109.5 | C4B—C5B—H5B3 | 109.5 |
H5A1—C5A—H5A3 | 109.5 | H5B1—C5B—H5B3 | 109.5 |
H5A2—C5A—H5A3 | 109.5 | H5B2—C5B—H5B3 | 109.5 |
C8A—C6A—C7A | 121.05 (17) | C8B—C6B—C7B | 120.83 (17) |
C8A—C6A—C4A | 121.24 (16) | C8B—C6B—C4B | 121.00 (16) |
C7A—C6A—C4A | 117.71 (16) | C7B—C6B—C4B | 118.17 (15) |
C6A—C7A—H7A1 | 109.5 | C6B—C7B—H7B1 | 109.5 |
C6A—C7A—H7A2 | 109.5 | C6B—C7B—H7B2 | 109.5 |
H7A1—C7A—H7A2 | 109.5 | H7B1—C7B—H7B2 | 109.5 |
C6A—C7A—H7A3 | 109.5 | C6B—C7B—H7B3 | 109.5 |
H7A1—C7A—H7A3 | 109.5 | H7B1—C7B—H7B3 | 109.5 |
H7A2—C7A—H7A3 | 109.5 | H7B2—C7B—H7B3 | 109.5 |
C6A—C8A—C9A | 126.53 (16) | C6B—C8B—C9B | 126.58 (16) |
C6A—C8A—H8A | 116.7 | C6B—C8B—H8B | 116.7 |
C9A—C8A—H8A | 116.7 | C9B—C8B—H8B | 116.7 |
C8A—C9A—C10A | 112.53 (14) | C8B—C9B—C10B | 111.61 (13) |
C8A—C9A—C2A | 111.81 (14) | C8B—C9B—C2B | 112.21 (13) |
C10A—C9A—C2A | 109.58 (14) | C10B—C9B—C2B | 110.33 (14) |
C8A—C9A—H9A | 107.6 | C8B—C9B—H9B | 107.5 |
C10A—C9A—H9A | 107.6 | C10B—C9B—H9B | 107.5 |
C2A—C9A—H9A | 107.6 | C2B—C9B—H9B | 107.5 |
C11A—C10A—C9A | 109.02 (14) | C11B—C10B—C9B | 109.79 (14) |
C11A—C10A—H10A | 109.9 | C11B—C10B—H10C | 109.7 |
C9A—C10A—H10A | 109.9 | C9B—C10B—H10C | 109.7 |
C11A—C10A—H10B | 109.9 | C11B—C10B—H10D | 109.7 |
C9A—C10A—H10B | 109.9 | C9B—C10B—H10D | 109.7 |
H10A—C10A—H10B | 108.3 | H10C—C10B—H10D | 108.2 |
O1A—C11A—C10A | 112.06 (13) | O1B—C11B—C10B | 112.44 (14) |
O1A—C11A—H11A | 109.2 | O1B—C11B—H11C | 109.1 |
C10A—C11A—H11A | 109.2 | C10B—C11B—H11C | 109.1 |
O1A—C11A—H11B | 109.2 | O1B—C11B—H11D | 109.1 |
C10A—C11A—H11B | 109.2 | C10B—C11B—H11D | 109.1 |
H11A—C11A—H11B | 107.9 | H11C—C11B—H11D | 107.8 |
C11A—O1A—C1A—O2A | −169.45 (15) | C11B—O1B—C1B—O2B | 172.37 (16) |
C11A—O1A—C1A—C2A | 14.7 (2) | C11B—O1B—C1B—C2B | −10.0 (2) |
O2A—C1A—C2A—C9A | 170.68 (16) | O2B—C1B—C2B—C9B | −171.53 (17) |
O1A—C1A—C2A—C9A | −13.6 (2) | O1B—C1B—C2B—C9B | 10.9 (2) |
O2A—C1A—C2A—C3A | −64.6 (2) | O2B—C1B—C2B—C3B | 63.0 (2) |
O1A—C1A—C2A—C3A | 111.15 (17) | O1B—C1B—C2B—C3B | −114.60 (18) |
C1A—C2A—C3A—C4A | 171.07 (14) | C1B—C2B—C3B—C4B | −172.97 (14) |
C9A—C2A—C3A—C4A | −61.18 (19) | C9B—C2B—C3B—C4B | 59.14 (19) |
C2A—C3A—C4A—C6A | 51.6 (2) | C2B—C3B—C4B—C6B | −50.73 (19) |
C2A—C3A—C4A—C5A | 177.22 (15) | C2B—C3B—C4B—C5B | −176.61 (15) |
C3A—C4A—C6A—C8A | −21.7 (2) | C3B—C4B—C6B—C8B | 21.6 (2) |
C5A—C4A—C6A—C8A | −144.93 (19) | C5B—C4B—C6B—C8B | 145.57 (18) |
C3A—C4A—C6A—C7A | 158.46 (17) | C3B—C4B—C6B—C7B | −159.38 (16) |
C5A—C4A—C6A—C7A | 35.2 (2) | C5B—C4B—C6B—C7B | −35.4 (2) |
C7A—C6A—C8A—C9A | 179.71 (17) | C7B—C6B—C8B—C9B | −178.78 (17) |
C4A—C6A—C8A—C9A | −0.1 (3) | C4B—C6B—C8B—C9B | 0.2 (3) |
C6A—C8A—C9A—C10A | 115.8 (2) | C6B—C8B—C9B—C10B | −117.37 (19) |
C6A—C8A—C9A—C2A | −8.0 (3) | C6B—C8B—C9B—C2B | 7.1 (3) |
C1A—C2A—C9A—C8A | 160.68 (14) | C1B—C2B—C9B—C8B | −159.62 (15) |
C3A—C2A—C9A—C8A | 37.52 (19) | C3B—C2B—C9B—C8B | −35.6 (2) |
C1A—C2A—C9A—C10A | 35.20 (19) | C1B—C2B—C9B—C10B | −34.48 (19) |
C3A—C2A—C9A—C10A | −87.96 (17) | C3B—C2B—C9B—C10B | 89.56 (17) |
C8A—C9A—C10A—C11A | 177.12 (14) | C8B—C9B—C10B—C11B | −177.13 (15) |
C2A—C9A—C10A—C11A | −57.82 (18) | C2B—C9B—C10B—C11B | 57.39 (18) |
C1A—O1A—C11A—C10A | −38.2 (2) | C1B—O1B—C11B—C10B | 33.4 (2) |
C9A—C10A—C11A—O1A | 59.84 (18) | C9B—C10B—C11B—O1B | −56.98 (19) |
D—H···A | D—H | H···A | D···A | D—H···A |
C8B—H8B···O2Ai | 0.95 | 2.48 | 3.304 (2) | 144 |
C9A—H9A···O1Aii | 1.00 | 2.80 | 3.577 (2) | 135 |
C11A—H11A···O2Aiii | 0.99 | 2.82 | 3.455 (2) | 122 |
C11A—H11B···O2Aiv | 0.99 | 2.55 | 3.510 (2) | 162 |
C9B—H9B···O1Bi | 1.00 | 2.88 | 3.569 (2) | 127 |
C9B—H9B···O1Bii | 1.00 | 2.76 | 3.529 (2) | 134 |
C11B—H11C···O2Bi | 0.99 | 2.61 | 3.567 (2) | 164 |
Symmetry codes: (i) −x+3/2, y−1/2, −z+1/2; (ii) x, y−1, z; (iii) −x+1/2, y+1/2, −z+1/2; (iv) −x+1/2, y−1/2, −z+1/2. |
Experimental details
Crystal data | |
Chemical formula | C11H16O2 |
Mr | 180.24 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 150 |
a, b, c (Å) | 14.2924 (17), 5.4060 (6), 25.969 (3) |
β (°) | 96.530 (2) |
V (Å3) | 1993.4 (4) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 0.08 |
Crystal size (mm) | 0.48 × 0.11 × 0.03 |
Data collection | |
Diffractometer | Bruker SMART CCD area-detector diffractometer |
Absorption correction | Multi-scan (SHELXTL/SADABS; Sheldrick, 1997) |
Tmin, Tmax | 0.938, 1.000 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 13507, 3517, 2526 |
Rint | 0.031 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.040, 0.100, 1.04 |
No. of reflections | 3517 |
No. of parameters | 239 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.21, −0.17 |
Computer programs: SMART (Bruker, 1998), SMART, SAINT (Bruker, 1998), SHELXS97 (Sheldrick, 1990), SHELXL97 (Sheldrick, 1997), SHELXTL (Sheldrick, 1998), SHELXTL.
D—H···A | D—H | H···A | D···A | D—H···A |
C8B—H8B···O2Ai | 0.95 | 2.48 | 3.304 (2) | 144 |
C9A—H9A···O1Aii | 1.00 | 2.80 | 3.577 (2) | 135 |
C11A—H11A···O2Aiii | 0.99 | 2.82 | 3.455 (2) | 122 |
C11A—H11B···O2Aiv | 0.99 | 2.55 | 3.510 (2) | 162 |
C9B—H9B···O1Bi | 1.00 | 2.88 | 3.569 (2) | 127 |
C9B—H9B···O1Bii | 1.00 | 2.76 | 3.529 (2) | 134 |
C11B—H11C···O2Bi | 0.99 | 2.61 | 3.567 (2) | 164 |
Symmetry codes: (i) −x+3/2, y−1/2, −z+1/2; (ii) x, y−1, z; (iii) −x+1/2, y+1/2, −z+1/2; (iv) −x+1/2, y−1/2, −z+1/2. |
The title lactone, (I), was prepared as an intermediate in the synthesis of an isomer of the oxaspirobicyclic tetronic acid unit of the CCK-B receptor antagonist tetronothiodin.
The asymmetric unit of (I) contains two independent molecules (Fig. 1) which are essentially superimposible. The structure confirms the expected geometry at atoms C2, C4 and C9 in each molecule and are are no unusual bond lengths or angles.
Fig. 2 shows the unit-cell packing; the molecules are stacked parallel to the b axis. There are indications of a weak C—H···O hydrogen bonds between neighbouring molecules; these are collected in Table 1 (Desiraju, 1996; Taylor & Kennard, 1982).