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The structure of title compound, C17H22O3S, reveals conjugation between the double bond within the cyclo­hexene ring and the exocyclic carbonyl, and, as a result, the three substituents at C1-C3 occupy equatorial positions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536801008248/ci6031sup1.cif
Contains datablocks general, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536801008248/ci6031Isup2.hkl
Contains datablock I

CCDC reference: 170304

Key indicators

  • Single-crystal X-ray study
  • T = 173 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.040
  • wR factor = 0.129
  • Data-to-parameter ratio = 19.5

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry








Computing details top

Data collection: MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1996); cell refinement: MSC/AFC Diffractometer Control Software; data reduction: TEXSAN for Windows (Molecular Structure Corporation, 1997); program(s) used to solve structure: SIR97 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); software used to prepare material for publication: SHELXL97.

(I) top
Crystal data top
C17H22O3SF(000) = 1312
Mr = 306.42Dx = 1.256 Mg m3
Orthorhombic, PbcaMo Kα radiation, λ = 0.71069 Å
Hall symbol: -P 2ac 2abCell parameters from 22 reflections
a = 16.560 (5) Åθ = 7.3–9.5°
b = 20.69 (1) ŵ = 0.21 mm1
c = 9.453 (2) ÅT = 173 K
V = 3240 (2) Å3Plate, colourless
Z = 80.37 × 0.37 × 0.11 mm
Data collection top
Rigaku AFC-7R
diffractometer
Rint = 0.000
Radiation source: Rotating anodeθmax = 27.5°, θmin = 3.2°
Graphite monochromatorh = 021
ω–2θ scansk = 026
4193 measured reflectionsl = 012
3725 independent reflections3 standard reflections every 400 reflections
1960 reflections with I > 2σ(I) intensity decay: 1.4%
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)] = 0.040Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.129H-atom parameters constrained
S = 1.01 w = 1/[σ2(Fo2) + (0.0508P)2 + 0.9004P]
where P = (Fo2 + 2Fc2)/3
3725 reflections(Δ/σ)max < 0.001
191 parametersΔρmax = 0.26 e Å3
0 restraintsΔρmin = 0.29 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
S220.02219 (4)0.19127 (3)0.22763 (6)0.03519 (17)
O10.17361 (11)0.07827 (9)0.46796 (19)0.0512 (5)
O22B0.02531 (12)0.13810 (10)0.12897 (18)0.0539 (5)
O22A0.01250 (10)0.25137 (10)0.1810 (2)0.0536 (5)
C10.13097 (15)0.06690 (11)0.5706 (3)0.0352 (6)
C20.04303 (14)0.07756 (11)0.5646 (2)0.0304 (5)
C30.00270 (14)0.06999 (10)0.6813 (3)0.0334 (5)
C3A0.09270 (15)0.07808 (14)0.6813 (3)0.0492 (7)
H3A0.11360.07040.77690.068 (2)*
H3B0.10640.12210.65160.068 (2)*
H3C0.11690.04700.61560.068 (2)*
C40.03308 (14)0.05177 (12)0.8219 (2)0.0350 (5)
H4A0.00380.07550.89700.0569 (18)*
H4B0.02380.00510.83770.0569 (18)*
C5B0.13756 (17)0.13810 (13)0.8524 (3)0.0464 (7)
H5D0.19550.14640.86270.068 (2)*
H5E0.11740.16030.76780.068 (2)*
H5F0.10900.15430.93600.068 (2)*
C50.12315 (15)0.06536 (11)0.8378 (2)0.0352 (6)
C5A0.15537 (18)0.03051 (15)0.9694 (3)0.0516 (7)
H5A0.21320.03940.97980.068 (2)*
H5B0.12660.04601.05330.068 (2)*
H5C0.14690.01610.95920.068 (2)*
C60.16562 (15)0.03995 (13)0.7052 (2)0.0400 (6)
H6A0.16130.00770.70310.0569 (18)*
H6B0.22370.05120.71040.0569 (18)*
C210.00986 (16)0.09645 (11)0.4215 (3)0.0381 (6)
H21A0.03250.06720.34870.0569 (18)*
H21B0.04950.09080.42190.0569 (18)*
C220.02976 (14)0.16600 (11)0.3824 (2)0.0310 (5)
H22A0.01490.19470.46200.0569 (18)*
H22B0.08870.17000.36680.0569 (18)*
C230.12096 (13)0.20705 (11)0.2865 (2)0.0300 (5)
C240.13626 (16)0.26362 (12)0.3608 (3)0.0393 (6)
H240.09380.29300.38160.0455 (14)*
C250.21442 (18)0.27655 (16)0.4038 (3)0.0535 (8)
H250.22620.31520.45410.0455 (14)*
C260.27501 (18)0.23340 (18)0.3737 (3)0.0607 (9)
H260.32870.24280.40220.0455 (14)*
C270.25936 (17)0.17729 (16)0.3036 (3)0.0584 (9)
H270.30180.14740.28650.0455 (14)*
C280.18207 (16)0.16343 (13)0.2570 (3)0.0421 (6)
H280.17120.12490.20590.0455 (14)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S220.0389 (3)0.0404 (3)0.0262 (3)0.0044 (3)0.0039 (3)0.0061 (3)
O10.0503 (11)0.0641 (13)0.0392 (11)0.0159 (10)0.0146 (9)0.0091 (9)
O22B0.0734 (13)0.0627 (13)0.0255 (8)0.0212 (11)0.0007 (9)0.0084 (9)
O22A0.0430 (10)0.0592 (11)0.0585 (12)0.0069 (9)0.0031 (10)0.0301 (10)
C10.0418 (14)0.0301 (13)0.0338 (13)0.0038 (11)0.0016 (11)0.0022 (10)
C20.0385 (13)0.0239 (11)0.0289 (12)0.0003 (10)0.0046 (9)0.0011 (9)
C30.0382 (12)0.0239 (11)0.0382 (13)0.0023 (10)0.0037 (10)0.0024 (10)
C3A0.0396 (14)0.0550 (17)0.0530 (17)0.0017 (13)0.0004 (13)0.0035 (14)
C40.0418 (14)0.0343 (12)0.0288 (11)0.0035 (10)0.0020 (10)0.0007 (10)
C5B0.0541 (16)0.0454 (16)0.0396 (14)0.0100 (13)0.0053 (13)0.0033 (12)
C50.0403 (14)0.0348 (13)0.0304 (12)0.0013 (11)0.0034 (10)0.0026 (10)
C5A0.0608 (19)0.0580 (18)0.0360 (15)0.0020 (14)0.0093 (13)0.0096 (13)
C60.0392 (14)0.0445 (15)0.0362 (14)0.0102 (11)0.0013 (11)0.0014 (12)
C210.0519 (16)0.0304 (12)0.0322 (12)0.0002 (11)0.0082 (11)0.0012 (10)
C220.0330 (12)0.0316 (12)0.0284 (11)0.0041 (10)0.0031 (10)0.0014 (9)
C230.0331 (11)0.0330 (12)0.0240 (11)0.0004 (9)0.0049 (9)0.0073 (9)
C240.0442 (14)0.0363 (14)0.0373 (14)0.0036 (11)0.0064 (11)0.0032 (11)
C250.0572 (18)0.0651 (19)0.0381 (16)0.0276 (16)0.0013 (13)0.0005 (14)
C260.0364 (15)0.090 (3)0.0552 (19)0.0126 (16)0.0037 (13)0.0317 (19)
C270.0392 (15)0.067 (2)0.068 (2)0.0134 (15)0.0155 (14)0.0306 (18)
C280.0472 (15)0.0392 (13)0.0399 (14)0.0083 (12)0.0124 (12)0.0093 (12)
Geometric parameters (Å, º) top
S22—O22A1.439 (2)C4—C51.525 (3)
S22—O22B1.4433 (19)C5B—C51.530 (4)
S22—C231.758 (2)C5—C5A1.534 (3)
S22—C221.776 (2)C5—C61.530 (3)
O1—C11.223 (3)C21—C221.522 (3)
C1—C21.474 (3)C23—C281.385 (3)
C1—C61.503 (3)C23—C241.388 (3)
C2—C31.347 (3)C24—C251.383 (4)
C2—C211.511 (3)C25—C261.373 (4)
C3—C41.504 (3)C26—C271.362 (4)
C3—C3A1.500 (3)C27—C281.384 (4)
O22A—S22—O22B118.37 (13)C4—C5—C5A109.5 (2)
O22A—S22—C23107.93 (11)C5B—C5—C5A109.6 (2)
O22B—S22—C23108.23 (12)C4—C5—C6107.8 (2)
O22A—S22—C22108.26 (12)C5B—C5—C6109.9 (2)
O22B—S22—C22108.98 (11)C5A—C5—C6110.1 (2)
C23—S22—C22104.14 (11)C1—C6—C5113.0 (2)
O1—C1—C2120.8 (2)C2—C21—C22112.53 (19)
O1—C1—C6121.5 (2)C21—C22—S22111.93 (16)
C2—C1—C6117.7 (2)C28—C23—C24121.2 (2)
C3—C2—C1120.4 (2)C28—C23—S22119.7 (2)
C3—C2—C21124.0 (2)C24—C23—S22119.10 (18)
C1—C2—C21115.6 (2)C25—C24—C23118.9 (3)
C2—C3—C4122.1 (2)C26—C25—C24119.8 (3)
C2—C3—C3A123.1 (2)C27—C26—C25121.1 (3)
C4—C3—C3A114.8 (2)C26—C27—C28120.5 (3)
C3—C4—C5115.2 (2)C27—C28—C23118.5 (3)
C4—C5—C5B110.0 (2)
 

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