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The title compound, C16H22O3S, exhibits a conformational arrangement that permits intramolecular O—H...O—S hydrogen bonds. Intermolecular bifurcated hydorgen bonding between the hydroxyl H and the sulfone O atoms, observed in the un­methyl­ated derivative, is disrupted by the presence of the methyl group at the 6-position.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804013650/tk6173sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804013650/tk6173Isup2.hkl
Contains datablock I

CCDC reference: 245283

Key indicators

  • Single-crystal X-ray study
  • T = 295 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.047
  • wR factor = 0.131
  • Data-to-parameter ratio = 19.3

checkCIF/PLATON results

No syntax errors found


No errors found in this datablock

Computing details top

Data collection: MSC/AFC-7 Diffractometer Control Software for Windows (Molecular Structure Corporation, 1999); cell refinement: MSC/AFC-7 Diffractometer Control Software for Windows; data reduction: TEXSAN for Windows (Molecular Structure Corporation, 1997-2001); program(s) used to solve structure: TEXSAN for Windows; program(s) used to refine structure: TEXSAN for Windows and SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2001) and ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: TEXSAN for Windows and PLATON.

(1RS,2SR,6SR,8SR)-2,6-Dimethyl-8-(phenylsulfonyl)bicyclo[4.2.0]octan-1-ol top
Crystal data top
C16H22O3SF(000) = 632
Mr = 294.41Dx = 1.274 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71069 Å
Hall symbol: -P 2ybcCell parameters from 25 reflections
a = 11.340 (3) Åθ = 12.6–17.4°
b = 18.026 (6) ŵ = 0.22 mm1
c = 7.8442 (16) ÅT = 295 K
β = 106.788 (18)°Prismatic, colorless
V = 1535.1 (7) Å30.40 × 0.35 × 0.20 mm
Z = 4
Data collection top
Rigaku AFC7R
diffractometer
Rint = 0.053
Radiation source: Rigaku rotating anodeθmax = 27.5°, θmin = 2.9°
Graphite monochromatorh = 614
ω–2θ scansk = 2310
4336 measured reflectionsl = 109
3518 independent reflections3 standard reflections every 150 reflections
1904 reflections with I > 2σ(I) intensity decay: 0.8%
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)] = 0.047Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.131H-atom parameters constrained
S = 1.00 w = 1/[σ2(Fo2) + (0.0382P)2 + 0.7618P]
where P = (Fo2 + 2Fc2)/3
3518 reflections(Δ/σ)max = 0.001
182 parametersΔρmax = 0.23 e Å3
0 restraintsΔρmin = 0.27 e Å3
Special details top

Experimental. The scan width was (1.73 + 0.30tanθ)° with an ω scan speed of 32° per minute (up to 4 scans to achieve I/σ(I) > 10). Stationary background counts were recorded at each end of the scan, and the scan time:background time ratio was 2:1.

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All e.s.d.'s are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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
S10.90969 (6)0.16012 (4)0.39004 (9)0.0456 (2)
O10.71411 (18)0.03138 (11)0.2793 (2)0.0507 (7)
O20.90428 (19)0.10497 (14)0.5212 (2)0.0692 (9)
O30.85807 (19)0.23176 (14)0.4021 (3)0.0756 (9)
C10.7226 (2)0.07423 (14)0.1306 (3)0.0341 (8)
C20.5979 (2)0.10972 (15)0.0463 (4)0.0446 (9)
C30.5818 (3)0.1358 (2)0.1426 (4)0.0658 (11)
C40.6154 (3)0.0759 (2)0.2569 (4)0.0730 (13)
C50.7501 (3)0.05653 (19)0.1807 (4)0.0574 (11)
C60.7821 (2)0.02628 (15)0.0098 (3)0.0410 (8)
C70.9097 (2)0.05481 (16)0.1220 (4)0.0457 (10)
C80.8440 (2)0.12203 (14)0.1755 (3)0.0341 (8)
C91.0664 (2)0.17158 (14)0.4001 (3)0.0373 (8)
C101.1041 (3)0.23599 (17)0.3343 (4)0.0510 (10)
C111.2270 (3)0.24290 (19)0.3410 (4)0.0596 (11)
C121.3087 (3)0.18687 (19)0.4123 (4)0.0536 (10)
C131.2708 (2)0.12324 (18)0.4775 (4)0.0507 (10)
C141.1482 (2)0.11496 (15)0.4713 (3)0.0436 (9)
C210.5701 (3)0.1701 (2)0.1637 (5)0.0705 (13)
C610.7603 (3)0.05727 (17)0.0121 (4)0.0588 (11)
H10.763900.053600.386700.0590*
H20.538200.071900.039100.0540*
H80.835200.160000.088700.0410*
H101.047000.274400.285800.0610*
H111.255000.286400.296300.0720*
H121.392800.192300.416700.0640*
H131.328300.085100.526400.0610*
H141.120700.071100.515400.0520*
H310.633200.177700.139500.0790*
H320.498200.149500.194400.0790*
H410.600900.093600.375200.0880*
H420.566600.033000.257400.0880*
H510.797500.100000.180500.0690*
H520.770700.020000.254600.0690*
H710.964500.067000.054700.0550*
H720.950500.023400.218300.0550*
H2110.485700.183700.120700.0850*
H2120.587200.152400.282300.0850*
H2130.620100.212200.161400.0850*
H6110.675400.067500.040800.0710*
H6120.807600.081800.053100.0710*
H6130.784400.074500.131600.0710*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0408 (3)0.0594 (5)0.0370 (3)0.0010 (4)0.0119 (3)0.0105 (3)
O10.0622 (12)0.0466 (12)0.0495 (11)0.0070 (10)0.0262 (10)0.0115 (9)
O20.0611 (13)0.111 (2)0.0369 (11)0.0165 (13)0.0162 (10)0.0112 (12)
O30.0557 (13)0.0799 (17)0.0855 (16)0.0164 (12)0.0114 (11)0.0450 (14)
C10.0346 (13)0.0325 (14)0.0388 (13)0.0013 (11)0.0165 (11)0.0044 (11)
C20.0346 (13)0.0380 (15)0.0600 (17)0.0004 (12)0.0119 (12)0.0001 (13)
C30.0522 (18)0.066 (2)0.064 (2)0.0014 (16)0.0074 (15)0.0136 (17)
C40.075 (2)0.097 (3)0.0397 (17)0.017 (2)0.0048 (16)0.0026 (18)
C50.0638 (19)0.070 (2)0.0437 (16)0.0172 (16)0.0239 (14)0.0114 (15)
C60.0377 (13)0.0421 (16)0.0472 (15)0.0042 (12)0.0188 (12)0.0088 (12)
C70.0345 (14)0.0555 (19)0.0512 (17)0.0013 (13)0.0191 (12)0.0111 (14)
C80.0332 (12)0.0376 (15)0.0327 (12)0.0024 (11)0.0114 (10)0.0004 (11)
C90.0383 (13)0.0404 (15)0.0298 (12)0.0016 (12)0.0046 (10)0.0039 (11)
C100.0552 (17)0.0458 (18)0.0460 (16)0.0023 (14)0.0051 (13)0.0086 (14)
C110.0599 (19)0.061 (2)0.0573 (19)0.0135 (16)0.0159 (16)0.0137 (16)
C120.0416 (15)0.067 (2)0.0520 (17)0.0093 (15)0.0131 (13)0.0077 (15)
C130.0412 (15)0.0508 (19)0.0540 (17)0.0027 (14)0.0040 (13)0.0076 (14)
C140.0443 (15)0.0398 (16)0.0420 (15)0.0035 (12)0.0049 (12)0.0016 (12)
C210.0501 (18)0.068 (2)0.092 (3)0.0195 (17)0.0185 (17)0.0139 (19)
C610.0559 (18)0.0437 (19)0.081 (2)0.0034 (14)0.0264 (16)0.0144 (16)
Geometric parameters (Å, º) top
S1—O21.445 (2)C13—C141.385 (3)
S1—O31.432 (3)C2—H20.9509
S1—C81.770 (2)C3—H310.9501
S1—C91.768 (3)C3—H320.9499
O1—C11.425 (3)C4—H410.9496
O1—H10.9561C4—H420.9503
C1—C21.519 (4)C5—H510.9500
C1—C61.571 (3)C5—H520.9500
C1—C81.575 (3)C7—H710.9501
C2—C211.517 (5)C7—H720.9505
C2—C31.514 (4)C8—H80.9501
C3—C41.521 (5)C10—H100.9493
C4—C51.512 (5)C11—H110.9502
C5—C61.533 (4)C12—H120.9494
C6—C71.548 (4)C13—H130.9489
C6—C611.527 (4)C14—H140.9510
C7—C81.543 (4)C21—H2110.9505
C9—C141.384 (4)C21—H2120.9490
C9—C101.387 (4)C21—H2130.9506
C10—C111.385 (5)C61—H6110.9499
C11—C121.375 (5)C61—H6120.9504
C12—C131.374 (5)C61—H6130.9497
S1···H12.5290H8···H312.4869
O1···O22.765 (3)H8···H512.3000
O1···C13i3.354 (4)H8···O3vii2.4972
O1···C14i3.385 (3)H10···O32.6725
O2···O12.765 (3)H11···C13vii3.0328
O2···C5ii3.413 (4)H11···C14vii3.0568
O1···H6132.4807H13···O1i2.7178
O1···H13i2.7178H14···O22.5421
O1···H14i2.7879H14···O1i2.7879
O1···H722.8595H31···C83.0684
O1···H2122.6173H31···H82.4869
O2···H11.8800H31···H512.4254
O2···H142.5421H31···H2132.4865
O3···H102.6725H31···H213vii2.5032
O3···H2132.8334H32···H2112.5907
O3···H8iii2.4972H42···C613.0429
C5···O2iv3.413 (4)H42···H22.5372
C7···C143.423 (4)H42···H6112.5456
C13···O1i3.354 (4)H51···C82.7172
C14···O1i3.385 (3)H51···H82.3000
C14···C73.423 (4)H51···H312.4254
C3···H82.9543H51···H712.3078
C4···H6113.0581H52···H6122.3788
C5···H82.7745H52···C13v3.0774
C7···H13.0047H71···H512.3078
C8···H2132.9897H72···O12.8595
C8···H512.7172H72···C143.0197
C8···H313.0684H72···H6132.5268
C13···H52v3.0774H211···H322.5907
C13···H11iii3.0328H212···O12.6173
C14···H723.0197H213···O32.8334
C14···H613i3.0730H213···C82.9897
C14···H11iii3.0568H213···H312.4865
C61···H423.0429H213···H31iii2.5032
H1···S12.5290H611···C43.0581
H1···O21.8800H611···H422.5456
H1···C73.0047H611···H2vi2.4274
H2···H422.5372H612···H522.3788
H2···H611vi2.4274H613···O12.4807
H8···C32.9543H613···H722.5268
H8···C52.7745H613···C14i3.0730
O2—S1—O3118.11 (14)C4—C3—H32108.75
O2—S1—C8108.50 (12)H31—C3—H32109.47
O2—S1—C9107.31 (12)C3—C4—H41109.60
O3—S1—C8110.16 (13)C3—C4—H42109.60
O3—S1—C9108.45 (13)C5—C4—H41109.51
C8—S1—C9103.25 (11)C5—C4—H42109.54
C1—O1—H1109.38H41—C4—H42109.46
O1—C1—C6109.7 (2)C4—C5—H51108.47
O1—C1—C8112.01 (18)C4—C5—H52108.50
C2—C1—C6118.5 (2)C6—C5—H51108.50
C2—C1—C8120.7 (2)C6—C5—H52108.52
C6—C1—C886.33 (17)H51—C5—H52109.51
O1—C1—C2108.1 (2)C6—C7—H71114.51
C1—C2—C3113.0 (2)C6—C7—H72114.48
C1—C2—C21111.6 (2)C8—C7—H71114.47
C3—C2—C21112.6 (3)C8—C7—H72114.47
C2—C3—C4112.1 (3)H71—C7—H72109.45
C3—C4—C5109.1 (3)S1—C8—H8109.27
C4—C5—C6113.3 (3)C1—C8—H8109.25
C1—C6—C788.17 (18)C7—C8—H8109.26
C1—C6—C61115.9 (2)C9—C10—H10120.78
C1—C6—C5111.7 (2)C11—C10—H10120.80
C5—C6—C61111.6 (2)C10—C11—H11120.00
C7—C6—C61116.7 (2)C12—C11—H11119.89
C5—C6—C7110.8 (2)C11—C12—H12119.38
C6—C7—C888.28 (18)C13—C12—H12119.43
S1—C8—C1121.69 (16)C12—C13—H13120.19
C1—C8—C788.23 (18)C14—C13—H13120.11
S1—C8—C7117.36 (18)C9—C14—H14120.53
S1—C9—C10119.7 (2)C13—C14—H14120.54
C10—C9—C14121.7 (2)C2—C21—H211109.53
S1—C9—C14118.67 (19)C2—C21—H212109.54
C9—C10—C11118.4 (3)C2—C21—H213109.37
C10—C11—C12120.1 (3)H211—C21—H212109.53
C11—C12—C13121.2 (3)H211—C21—H213109.41
C12—C13—C14119.7 (3)H212—C21—H213109.44
C9—C14—C13118.9 (2)C6—C61—H611109.47
C1—C2—H2106.34C6—C61—H612109.51
C3—C2—H2106.37C6—C61—H613109.44
C21—C2—H2106.34H611—C61—H612109.45
C2—C3—H31108.79H611—C61—H613109.52
C2—C3—H32108.82H612—C61—H613109.44
C4—C3—H31108.86
O2—S1—C8—C142.2 (2)C8—C1—C6—C589.5 (2)
O2—S1—C8—C764.0 (2)C8—C1—C6—C722.17 (18)
O3—S1—C8—C188.5 (2)C8—C1—C6—C61141.1 (2)
O3—S1—C8—C7165.31 (19)O1—C1—C8—S133.8 (3)
C9—S1—C8—C1155.83 (19)C2—C1—C6—C7145.4 (2)
C9—S1—C8—C749.7 (2)C2—C1—C6—C6195.7 (3)
O2—S1—C9—C10159.0 (2)C1—C2—C3—C449.8 (3)
O2—S1—C9—C1422.1 (2)C21—C2—C3—C4177.5 (3)
O3—S1—C9—C1030.4 (2)C2—C3—C4—C562.5 (4)
O3—S1—C9—C14150.7 (2)C3—C4—C5—C660.9 (4)
C8—S1—C9—C1086.5 (2)C4—C5—C6—C145.7 (3)
C8—S1—C9—C1492.5 (2)C4—C5—C6—C6185.8 (3)
C6—C1—C2—C336.0 (3)C4—C5—C6—C7142.3 (3)
O1—C1—C2—C2170.3 (3)C1—C6—C7—C822.62 (18)
O1—C1—C6—C6129.0 (3)C61—C6—C7—C8140.8 (2)
C2—C1—C6—C533.6 (3)C5—C6—C7—C890.0 (2)
C6—C1—C2—C21164.1 (2)C6—C7—C8—S1147.71 (18)
C8—C1—C2—C367.7 (3)C6—C7—C8—C122.56 (18)
C8—C1—C2—C2160.4 (3)S1—C9—C10—C11178.9 (2)
O1—C1—C6—C5158.4 (2)C10—C9—C14—C130.3 (4)
O1—C1—C6—C789.9 (2)C14—C9—C10—C110.0 (4)
O1—C1—C2—C3161.6 (2)S1—C9—C14—C13179.2 (2)
O1—C1—C8—C787.6 (2)C9—C10—C11—C120.3 (4)
C2—C1—C8—S195.1 (3)C10—C11—C12—C130.2 (5)
C2—C1—C8—C7143.4 (2)C11—C12—C13—C140.2 (5)
C6—C1—C8—S1143.66 (19)C12—C13—C14—C90.4 (4)
C6—C1—C8—C722.25 (18)
Symmetry codes: (i) x+2, y, z+1; (ii) x, y, z+1; (iii) x, y+1/2, z+1/2; (iv) x, y, z1; (v) x+2, y, z; (vi) x+1, y, z; (vii) x, y+1/2, z1/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···O20.96001.88002.765 (3)153.00
C8—H8···O3vii0.95002.50003.431 (4)167.00
C14—H14···O20.95002.54002.909 (3)103.00
Symmetry code: (vii) x, y+1/2, z1/2.
 

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