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The sterochemistry of the title epoxide, C14H22O5S, has been established by single-crystal X-ray diffraction. The compound exhibits an unusually short inter­molecular C—H...O contact of 2.30 Å between the epoxide O atom and the epoxide C—H unit of a neighbouring mol­ecule.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806008002/at2013sup1.cif
Contains datablocks global, II

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806008002/at2013IIsup2.hkl
Contains datablock II

CCDC reference: 604954

Key indicators

  • Single-crystal X-ray study
  • T = 100 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.045
  • wR factor = 0.120
  • Data-to-parameter ratio = 19.8

checkCIF/PLATON results

No syntax errors found



Alert level A SYMM004_ALERT_1_A _symmetry_equiv_pos_as_xyz loop is missing. The symmetry equivalent positions in xyz. The following tests will not be performed. CELLZ_01,CHEMW_03,REFLT_03,SYMMG_01,SYMMG_02 ATOM006_ALERT_1_A _atom_site_U_iso_or_equiv is missing Isotropic atomic displacement paramter, or equivalent from anisotropic atomic displacement parameters. PLAT124_ALERT_1_A Uninterpretable or Absent _symmetry_equiv_pos_as_xyz . ?
Alert level C ABSTM02_ALERT_3_C The ratio of expected to reported Tmax/Tmin(RR') is < 0.90 Tmin and Tmax reported: 0.722 0.908 Tmin(prime) and Tmax expected: 0.882 0.908 RR(prime) = 0.818 Please check that your absorption correction is appropriate. PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large ............. 0.82 PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density .... 2.85 PLAT338_ALERT_2_C Small Average Tau in cyclohexane C1 -C9A 34.93 Deg.
3 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 4 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 2 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Bruker, 2002); cell refinement: SAINT-Plus (Bruker, 2003); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXTL (Bruker, 2000); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

(3RS,4RS,4aSR,7SR,9aRS)-7-tert-Butyl-9a-methyl-5,5-dioxo-3,4-epoxy- 1,2,3,4,4a,9a-hexahydro-8-oxa-5λ6-thiabenzocycloheptan-9-one top
Crystal data top
C14H22O5SF(000) = 648
Mr = 302.38Dx = 1.360 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 6709 reflections
a = 11.9812 (9) Åθ = 2.8–30.5°
b = 5.6631 (4) ŵ = 0.24 mm1
c = 21.7870 (17) ÅT = 100 K
β = 92.099 (1)°Block, colourless
V = 1477.27 (19) Å30.52 × 0.46 × 0.41 mm
Z = 4
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer
3659 independent reflections
Radiation source: fine-focus sealed tube3423 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.033
ω scansθmax = 28.3°, θmin = 1.9°
Absorption correction: multi-scan
(SADABS in SAINT-Plus; Bruker, 2003)
h = 1515
Tmin = 0.722, Tmax = 0.908k = 77
14255 measured reflectionsl = 2929
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)] = 0.045Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.120H-atom parameters constrained
S = 1.16 w = 1/[σ2(Fo2) + (0.0599P)2 + 0.8178P]
where P = (Fo2 + 2Fc2)/3
3659 reflections(Δ/σ)max < 0.001
185 parametersΔρmax = 0.69 e Å3
0 restraintsΔρmin = 0.24 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
C10.12550 (12)0.0376 (3)0.12212 (7)0.0179 (3)
H1A0.14480.04780.08350.021*
H1B0.09120.07690.15150.021*
O10.13080 (10)0.2137 (2)0.24871 (5)0.0260 (3)
S10.11163 (3)0.22363 (7)0.212500 (15)0.01658 (12)
C20.23199 (13)0.1375 (3)0.14866 (7)0.0222 (3)
H2A0.27490.22330.11600.027*
H2B0.27890.00560.16270.027*
O20.10017 (9)0.0305 (2)0.20609 (5)0.0207 (2)
C30.20738 (13)0.3017 (3)0.20139 (8)0.0232 (3)
H30.27220.39500.21590.028*
O30.11512 (10)0.3240 (2)0.27327 (5)0.0242 (3)
C40.09597 (13)0.4099 (3)0.21211 (7)0.0204 (3)
H40.09510.56730.23290.025*
C4A0.00207 (12)0.3652 (3)0.16872 (6)0.0150 (3)
H4A0.02590.52320.15580.018*
O40.07018 (9)0.0737 (2)0.06183 (5)0.0217 (2)
C60.23784 (12)0.3101 (3)0.17760 (7)0.0184 (3)
H6A0.24120.48470.17620.022*
H6B0.30210.25450.20350.022*
C70.24892 (12)0.2143 (3)0.11293 (7)0.0161 (3)
H70.25260.03800.11470.019*
O80.14644 (8)0.28478 (18)0.07957 (5)0.0154 (2)
C90.06135 (12)0.1237 (3)0.08062 (6)0.0159 (3)
C9A0.04078 (12)0.2326 (2)0.10908 (6)0.0139 (3)
C100.34941 (12)0.3071 (3)0.07855 (7)0.0185 (3)
C110.34610 (13)0.5764 (3)0.07343 (8)0.0223 (3)
H11A0.35850.64620.11430.033*
H11B0.27300.62590.05640.033*
H11C0.40460.62960.04640.033*
C120.45727 (13)0.2318 (3)0.11336 (9)0.0263 (4)
H12A0.52180.27510.08940.039*
H12B0.45660.06040.11970.039*
H12C0.46230.31160.15330.039*
C130.34540 (14)0.1997 (3)0.01390 (8)0.0235 (3)
H13A0.41100.25100.00810.035*
H13B0.27740.25250.00850.035*
H13C0.34510.02710.01690.035*
C140.09072 (12)0.4164 (3)0.06400 (7)0.0182 (3)
H14A0.03300.53080.05360.027*
H14B0.15250.49870.08310.027*
H14C0.11850.33680.02650.027*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0156 (6)0.0150 (7)0.0230 (7)0.0012 (5)0.0002 (5)0.0008 (5)
O10.0268 (6)0.0310 (7)0.0205 (6)0.0036 (5)0.0058 (5)0.0039 (5)
S10.01760 (19)0.0189 (2)0.01301 (19)0.00103 (13)0.00225 (13)0.00112 (12)
C20.0161 (7)0.0235 (8)0.0272 (8)0.0016 (6)0.0031 (6)0.0002 (6)
O20.0224 (5)0.0172 (5)0.0221 (5)0.0004 (4)0.0037 (4)0.0038 (4)
C30.0197 (7)0.0254 (8)0.0248 (8)0.0022 (6)0.0064 (6)0.0002 (6)
O30.0279 (6)0.0305 (6)0.0139 (5)0.0022 (5)0.0019 (4)0.0014 (4)
C40.0231 (7)0.0196 (7)0.0189 (7)0.0007 (6)0.0045 (6)0.0017 (6)
C4A0.0167 (6)0.0137 (6)0.0148 (6)0.0009 (5)0.0006 (5)0.0001 (5)
O40.0188 (5)0.0185 (5)0.0275 (6)0.0007 (4)0.0007 (4)0.0078 (4)
C60.0164 (7)0.0213 (7)0.0173 (7)0.0020 (5)0.0030 (5)0.0002 (5)
C70.0126 (6)0.0174 (7)0.0182 (7)0.0007 (5)0.0023 (5)0.0006 (5)
O80.0119 (5)0.0174 (5)0.0166 (5)0.0004 (4)0.0017 (4)0.0003 (4)
C90.0148 (6)0.0183 (7)0.0142 (6)0.0009 (5)0.0020 (5)0.0007 (5)
C9A0.0138 (6)0.0131 (6)0.0147 (6)0.0002 (5)0.0003 (5)0.0009 (5)
C100.0134 (6)0.0201 (7)0.0221 (7)0.0000 (5)0.0002 (5)0.0014 (6)
C110.0214 (7)0.0176 (7)0.0279 (8)0.0030 (6)0.0012 (6)0.0029 (6)
C120.0136 (7)0.0305 (9)0.0344 (9)0.0006 (6)0.0025 (6)0.0065 (7)
C130.0215 (7)0.0254 (8)0.0241 (8)0.0011 (6)0.0057 (6)0.0000 (6)
C140.0185 (7)0.0183 (7)0.0175 (6)0.0031 (5)0.0017 (5)0.0016 (5)
Geometric parameters (Å, º) top
C1—C21.529 (2)C6—H6B0.9900
C1—C9A1.534 (2)C7—O81.4594 (17)
C1—H1A0.9900C7—C101.534 (2)
C1—H1B0.9900C7—H71.0000
O1—C41.4385 (19)O8—C91.3688 (17)
O1—C31.443 (2)C9—C9A1.5223 (19)
S1—O31.4401 (11)C9A—C141.5370 (19)
S1—O21.4518 (12)C10—C111.530 (2)
S1—C61.7858 (15)C10—C131.533 (2)
S1—C4A1.8201 (14)C10—C121.535 (2)
C2—C31.499 (2)C11—H11A0.9800
C2—H2A0.9900C11—H11B0.9800
C2—H2B0.9900C11—H11C0.9800
C3—C41.480 (2)C12—H12A0.9800
C3—H31.0000C12—H12B0.9800
C4—C4A1.517 (2)C12—H12C0.9800
C4—H41.0000C13—H13A0.9800
C4A—C9A1.5565 (19)C13—H13B0.9800
C4A—H4A1.0000C13—H13C0.9800
O4—C91.1967 (18)C14—H14A0.9800
C6—C71.520 (2)C14—H14B0.9800
C6—H6A0.9900C14—H14C0.9800
C2—C1—C9A111.77 (12)C6—C7—C10115.29 (12)
C2—C1—H1A109.3O8—C7—H7109.1
C9A—C1—H1A109.3C6—C7—H7109.1
C2—C1—H1B109.3C10—C7—H7109.1
C9A—C1—H1B109.3C9—O8—C7115.03 (11)
H1A—C1—H1B107.9O4—C9—O8122.80 (13)
C4—O1—C361.78 (10)O4—C9—C9A126.89 (13)
O3—S1—O2118.63 (7)O8—C9—C9A110.31 (12)
O3—S1—C6106.66 (7)C9—C9A—C1109.33 (12)
O2—S1—C6108.03 (7)C9—C9A—C14108.30 (11)
O3—S1—C4A107.70 (7)C1—C9A—C14111.17 (12)
O2—S1—C4A108.65 (7)C9—C9A—C4A108.42 (11)
C6—S1—C4A106.57 (7)C1—C9A—C4A111.82 (12)
C3—C2—C1112.09 (13)C14—C9A—C4A107.70 (11)
C3—C2—H2A109.2C11—C10—C13109.17 (13)
C1—C2—H2A109.2C11—C10—C7111.00 (13)
C3—C2—H2B109.2C13—C10—C7108.30 (12)
C1—C2—H2B109.2C11—C10—C12109.41 (13)
H2A—C2—H2B107.9C13—C10—C12109.96 (13)
O1—C3—C458.94 (10)C7—C10—C12108.99 (12)
O1—C3—C2115.81 (14)C10—C11—H11A109.5
C4—C3—C2121.93 (13)C10—C11—H11B109.5
O1—C3—H3115.9H11A—C11—H11B109.5
C4—C3—H3115.9C10—C11—H11C109.5
C2—C3—H3115.9H11A—C11—H11C109.5
O1—C4—C359.27 (10)H11B—C11—H11C109.5
O1—C4—C4A116.95 (13)C10—C12—H12A109.5
C3—C4—C4A121.19 (13)C10—C12—H12B109.5
O1—C4—H4115.8H12A—C12—H12B109.5
C3—C4—H4115.8C10—C12—H12C109.5
C4A—C4—H4115.8H12A—C12—H12C109.5
C4—C4A—C9A113.31 (12)H12B—C12—H12C109.5
C4—C4A—S1107.75 (10)C10—C13—H13A109.5
C9A—C4A—S1114.81 (10)C10—C13—H13B109.5
C4—C4A—H4A106.8H13A—C13—H13B109.5
C9A—C4A—H4A106.8C10—C13—H13C109.5
S1—C4A—H4A106.8H13A—C13—H13C109.5
C7—C6—S1113.63 (10)H13B—C13—H13C109.5
C7—C6—H6A108.8C9A—C14—H14A109.5
S1—C6—H6A108.8C9A—C14—H14B109.5
C7—C6—H6B108.8H14A—C14—H14B109.5
S1—C6—H6B108.8C9A—C14—H14C109.5
H6A—C6—H6B107.7H14A—C14—H14C109.5
O8—C7—C6105.28 (11)H14B—C14—H14C109.5
O8—C7—C10108.93 (11)
C9A—C1—C2—C349.65 (18)C10—C7—O8—C9144.48 (12)
C4—O1—C3—C2113.24 (15)C7—O8—C9—O458.53 (18)
C1—C2—C3—O149.75 (18)C7—O8—C9—C9A120.80 (12)
C1—C2—C3—C418.3 (2)O4—C9—C9A—C111.0 (2)
C3—O1—C4—C4A111.94 (15)O8—C9—C9A—C1168.28 (11)
C2—C3—C4—O1102.92 (17)O4—C9—C9A—C14110.26 (16)
O1—C3—C4—C4A104.86 (16)O8—C9—C9A—C1470.45 (14)
C2—C3—C4—C4A1.9 (2)O4—C9—C9A—C4A133.15 (15)
O1—C4—C4A—C9A77.83 (16)O8—C9—C9A—C4A46.15 (15)
C3—C4—C4A—C9A9.1 (2)C2—C1—C9A—C9177.92 (12)
O1—C4—C4A—S150.31 (15)C2—C1—C9A—C1458.41 (16)
C3—C4—C4A—S1119.08 (14)C2—C1—C9A—C4A62.00 (15)
O3—S1—C4A—C435.97 (12)C4—C4A—C9A—C9160.61 (12)
O2—S1—C4A—C493.71 (11)S1—C4A—C9A—C936.22 (14)
C6—S1—C4A—C4150.11 (10)C4—C4A—C9A—C140.00 (16)
O3—S1—C4A—C9A163.24 (10)S1—C4A—C9A—C184.39 (13)
O2—S1—C4A—C9A33.56 (12)C4—C4A—C9A—C1482.41 (14)
C6—S1—C4A—C9A82.61 (11)S1—C4A—C9A—C14153.19 (10)
O3—S1—C6—C7178.91 (11)O8—C7—C10—C1159.79 (16)
O2—S1—C6—C750.35 (12)C6—C7—C10—C1158.25 (17)
C4A—S1—C6—C766.24 (12)O8—C7—C10—C1360.04 (15)
S1—C6—C7—O853.26 (14)C6—C7—C10—C13178.08 (12)
S1—C6—C7—C10173.32 (10)O8—C7—C10—C12179.64 (12)
C6—C7—O8—C991.34 (14)C6—C7—C10—C1262.31 (17)
 

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