The title compound, C15H20O3S, shows a conformational arrangement of the phenyl ring that permits hydrogen-bonded dimers to be disposed about a centre of symmetry.
Supporting information
CCDC reference: 245282
Key indicators
- Single-crystal X-ray study
- T = 295 K
- Mean (C-C) = 0.006 Å
- R factor = 0.053
- wR factor = 0.174
- Data-to-parameter ratio = 20.3
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low .... 49 Perc.
PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.15 Ratio
PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.12 Ratio
PLAT241_ALERT_2_C Check High U(eq) as Compared to Neighbors .... C4
PLAT242_ALERT_2_C Check Low U(eq) as Compared to Neighbors .... C2
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 6
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
6 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
3 ALERT type 2 Indicator that the structure model may be wrong or deficient
3 ALERT type 3 Indicator that the structure quality may be low
0 ALERT type 4 Improvement, methodology, query or suggestion
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,2RS,6SR,8SR)-2-Methyl-8-(phenylsulfonyl)bicyclo[4.2.0]octan-1-ol
top
Crystal data top
C15H20O3S | F(000) = 600 |
Mr = 280.38 | Dx = 1.217 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71069 Å |
Hall symbol: -P 2yn | Cell parameters from 24 reflections |
a = 12.328 (6) Å | θ = 12.8–16.0° |
b = 10.362 (4) Å | µ = 0.21 mm−1 |
c = 12.149 (2) Å | T = 295 K |
β = 99.60 (3)° | Prismatic, colorless |
V = 1530.2 (10) Å3 | 0.30 × 0.20 × 0.10 mm |
Z = 4 | |
Data collection top
Rigaku AFC7R diffractometer | Rint = 0.067 |
Radiation source: Rigaku rotating anode | θmax = 27.5°, θmin = 2.6° |
Graphite monochromator | h = −7→16 |
ω–2θ scans | k = 0→13 |
3987 measured reflections | l = −15→15 |
3516 independent reflections | 3 standard reflections every 150 reflections |
1717 reflections with I > 2σ(I) | intensity decay: 0.04% |
Refinement top
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)] = 0.053 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.174 | H-atom parameters constrained |
S = 0.98 | w = 1/[σ2(Fo2) + (0.0801P)2] where P = (Fo2 + 2Fc2)/3 |
3516 reflections | (Δ/σ)max = 0.001 |
173 parameters | Δρmax = 0.29 e Å−3 |
0 restraints | Δρmin = −0.35 e Å−3 |
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 | x | y | z | Uiso*/Ueq | |
S1 | 1.00472 (7) | 0.23346 (7) | 0.97401 (7) | 0.0400 (2) | |
O1 | 0.80786 (18) | 0.4144 (2) | 1.00962 (19) | 0.0547 (8) | |
O2 | 1.04527 (19) | 0.3640 (2) | 0.98511 (19) | 0.0524 (8) | |
O3 | 1.08393 (18) | 0.1299 (2) | 0.98802 (18) | 0.0511 (8) | |
C1 | 0.8366 (3) | 0.3199 (3) | 1.0922 (3) | 0.0476 (11) | |
C2 | 0.7296 (3) | 0.2644 (4) | 1.1213 (4) | 0.0712 (16) | |
C3 | 0.6894 (5) | 0.3539 (6) | 1.2090 (6) | 0.116 (3) | |
C4 | 0.7761 (6) | 0.3549 (7) | 1.3144 (5) | 0.129 (3) | |
C5 | 0.8815 (5) | 0.4138 (5) | 1.2966 (4) | 0.103 (2) | |
C6 | 0.9210 (3) | 0.3577 (3) | 1.1938 (3) | 0.0587 (11) | |
C7 | 0.9729 (3) | 0.2230 (3) | 1.1925 (3) | 0.0563 (11) | |
C8 | 0.9148 (3) | 0.2058 (3) | 1.0704 (3) | 0.0430 (10) | |
C9 | 0.9238 (3) | 0.2163 (3) | 0.8407 (3) | 0.0413 (9) | |
C10 | 0.8915 (3) | 0.3247 (3) | 0.7759 (3) | 0.0587 (12) | |
C11 | 0.8317 (4) | 0.3078 (4) | 0.6704 (3) | 0.0731 (16) | |
C12 | 0.8065 (3) | 0.1852 (4) | 0.6301 (3) | 0.0702 (14) | |
C13 | 0.8379 (3) | 0.0796 (4) | 0.6946 (3) | 0.0663 (14) | |
C14 | 0.8958 (3) | 0.0948 (3) | 0.8007 (3) | 0.0554 (11) | |
C21 | 0.6449 (4) | 0.2387 (5) | 1.0187 (5) | 0.108 (3) | |
H1 | 0.87170 | 0.46700 | 1.00580 | 0.0630* | |
H2 | 0.74700 | 0.18380 | 1.15730 | 0.0800* | |
H6 | 0.96960 | 0.41890 | 1.17210 | 0.0710* | |
H8 | 0.87530 | 0.12580 | 1.05740 | 0.0510* | |
H10 | 0.91070 | 0.40880 | 0.80540 | 0.0680* | |
H11 | 0.80990 | 0.38130 | 0.62490 | 0.0870* | |
H12 | 0.76660 | 0.17440 | 0.55630 | 0.0850* | |
H13 | 0.82010 | −0.00420 | 0.66690 | 0.0830* | |
H14 | 0.91850 | 0.02200 | 0.84640 | 0.0660* | |
H31 | 0.62110 | 0.32260 | 1.22240 | 0.1410* | |
H32 | 0.67940 | 0.43830 | 1.17610 | 0.1410* | |
H41 | 0.74620 | 0.40770 | 1.36720 | 0.1590* | |
H42 | 0.78600 | 0.27090 | 1.34050 | 0.1590* | |
H51 | 0.93270 | 0.39250 | 1.36000 | 0.1370* | |
H52 | 0.87120 | 0.50130 | 1.28710 | 0.1370* | |
H71 | 0.95100 | 0.16360 | 1.24440 | 0.0670* | |
H72 | 1.05120 | 0.22430 | 1.20140 | 0.0670* | |
H211 | 0.62360 | 0.31940 | 0.98370 | 0.1300* | |
H212 | 0.58200 | 0.20020 | 1.04180 | 0.1300* | |
H213 | 0.67440 | 0.18440 | 0.97040 | 0.1300* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
S1 | 0.0431 (4) | 0.0344 (4) | 0.0418 (4) | −0.0008 (4) | 0.0054 (3) | −0.0012 (3) |
O1 | 0.0469 (13) | 0.0493 (13) | 0.0682 (15) | 0.0036 (10) | 0.0103 (11) | 0.0194 (11) |
O2 | 0.0601 (14) | 0.0368 (11) | 0.0593 (14) | −0.0112 (11) | 0.0072 (11) | −0.0022 (10) |
O3 | 0.0543 (13) | 0.0465 (13) | 0.0516 (13) | 0.0117 (10) | 0.0063 (11) | −0.0010 (10) |
C1 | 0.0523 (19) | 0.0433 (17) | 0.0488 (19) | 0.0045 (15) | 0.0129 (15) | 0.0104 (15) |
C2 | 0.061 (2) | 0.073 (3) | 0.085 (3) | −0.002 (2) | 0.028 (2) | 0.024 (2) |
C3 | 0.097 (4) | 0.141 (5) | 0.132 (5) | 0.027 (4) | 0.080 (4) | 0.035 (4) |
C4 | 0.152 (6) | 0.155 (6) | 0.099 (4) | 0.025 (5) | 0.072 (4) | −0.004 (4) |
C5 | 0.137 (5) | 0.113 (4) | 0.065 (3) | 0.047 (4) | 0.030 (3) | −0.014 (3) |
C6 | 0.075 (2) | 0.0494 (19) | 0.051 (2) | 0.0091 (18) | 0.0088 (18) | −0.0076 (16) |
C7 | 0.072 (2) | 0.054 (2) | 0.0425 (18) | 0.0084 (19) | 0.0082 (16) | 0.0074 (15) |
C8 | 0.0528 (19) | 0.0327 (16) | 0.0440 (17) | −0.0021 (14) | 0.0095 (14) | 0.0044 (12) |
C9 | 0.0430 (16) | 0.0415 (17) | 0.0394 (16) | −0.0021 (14) | 0.0069 (13) | 0.0003 (13) |
C10 | 0.070 (2) | 0.048 (2) | 0.055 (2) | −0.0039 (18) | 0.0013 (18) | 0.0117 (16) |
C11 | 0.081 (3) | 0.073 (3) | 0.058 (2) | 0.004 (2) | −0.010 (2) | 0.022 (2) |
C12 | 0.067 (2) | 0.090 (3) | 0.048 (2) | −0.005 (2) | −0.0070 (19) | −0.002 (2) |
C13 | 0.078 (3) | 0.061 (2) | 0.053 (2) | −0.007 (2) | −0.0093 (19) | −0.0077 (18) |
C14 | 0.069 (2) | 0.0422 (18) | 0.052 (2) | −0.0014 (17) | 0.0010 (17) | −0.0034 (15) |
C21 | 0.057 (3) | 0.130 (5) | 0.136 (5) | −0.025 (3) | 0.013 (3) | 0.039 (4) |
Geometric parameters (Å, º) top
S1—O2 | 1.441 (2) | C13—C14 | 1.374 (5) |
S1—O3 | 1.442 (2) | C2—H2 | 0.9505 |
S1—C8 | 1.765 (4) | C3—H31 | 0.9415 |
S1—C9 | 1.764 (4) | C3—H32 | 0.9609 |
O1—C1 | 1.404 (4) | C4—H41 | 0.9621 |
O1—H1 | 0.9648 | C4—H42 | 0.9274 |
C1—C2 | 1.533 (5) | C5—H51 | 0.9371 |
C1—C8 | 1.576 (5) | C5—H52 | 0.9201 |
C1—C6 | 1.527 (5) | C6—H6 | 0.9398 |
C2—C21 | 1.510 (7) | C7—H71 | 0.9519 |
C2—C3 | 1.555 (8) | C7—H72 | 0.9533 |
C3—C4 | 1.525 (10) | C8—H8 | 0.9610 |
C4—C5 | 1.484 (10) | C10—H10 | 0.9569 |
C5—C6 | 1.529 (6) | C11—H11 | 0.9530 |
C6—C7 | 1.537 (5) | C12—H12 | 0.9546 |
C7—C8 | 1.546 (5) | C13—H13 | 0.9438 |
C9—C14 | 1.373 (5) | C14—H14 | 0.9507 |
C9—C10 | 1.391 (5) | C21—H211 | 0.9549 |
C10—C11 | 1.379 (5) | C21—H212 | 0.9549 |
C11—C12 | 1.378 (6) | C21—H213 | 0.9297 |
C12—C13 | 1.364 (6) | | |
| | | |
S1···H1 | 2.9842 | H1···H6 | 2.2302 |
S1···H6 | 3.1653 | H1···O2ii | 2.0221 |
O1···O2 | 3.036 (4) | H2···C7 | 2.7760 |
O1···C9 | 3.383 (4) | H2···H8 | 2.2307 |
O1···C10 | 3.312 (5) | H2···H42 | 2.3754 |
O1···C13i | 3.291 (5) | H2···H71 | 2.5692 |
O1···O2ii | 2.918 (3) | H2···H52vii | 2.5464 |
O2···C6 | 3.174 (5) | H6···S1 | 3.1653 |
O2···O1ii | 2.918 (3) | H6···O2 | 2.6573 |
O2···O2ii | 3.075 (3) | H6···H1 | 2.2302 |
O2···O1 | 3.036 (4) | H6···H10ii | 2.3033 |
O1···H213 | 2.8901 | H8···C21 | 3.0351 |
O1···H12i | 2.9150 | H8···H2 | 2.2307 |
O1···H211 | 2.4474 | H8···H213 | 2.5975 |
O1···H13i | 2.5828 | H8···O3iv | 2.7694 |
O1···H32 | 2.7800 | H10···O2 | 2.5547 |
O2···H10 | 2.5547 | H10···H6ii | 2.3033 |
O2···H1 | 2.4414 | H12···O1vi | 2.9150 |
O2···H6 | 2.6573 | H12···O2viii | 2.7503 |
O2···H1ii | 2.0221 | H13···O1vi | 2.5828 |
O2···H12iii | 2.7503 | H14···O3 | 2.6831 |
O3···H14 | 2.6831 | H14···O3iv | 2.5583 |
O3···H72 | 2.8616 | H14···C7iv | 2.9448 |
O3···H8iv | 2.7694 | H31···H212 | 2.5104 |
O3···H14iv | 2.5583 | H31···C9ix | 3.0513 |
O3···H41v | 2.6996 | H32···O1 | 2.7800 |
C6···O2 | 3.174 (5) | H32···C6 | 3.0661 |
C9···O1 | 3.383 (4) | H41···O3ix | 2.6996 |
C10···O1 | 3.312 (5) | H42···H2 | 2.3754 |
C13···O1vi | 3.291 (5) | H52···H2x | 2.5464 |
C2···H71 | 3.0685 | H71···C2 | 3.0685 |
C6···H32 | 3.0661 | H71···H2 | 2.5692 |
C7···H14iv | 2.9448 | H72···O3 | 2.8616 |
C7···H2 | 2.7760 | H211···O1 | 2.4474 |
C8···H213 | 3.0179 | H212···H31 | 2.5104 |
C9···H31v | 3.0513 | H213···O1 | 2.8901 |
C21···H8 | 3.0351 | H213···C8 | 3.0179 |
H1···S1 | 2.9842 | H213···H8 | 2.5975 |
H1···O2 | 2.4414 | | |
| | | |
O2—S1—O3 | 118.05 (14) | C4—C3—H32 | 111.49 |
O2—S1—C8 | 109.69 (15) | H31—C3—H32 | 109.21 |
O2—S1—C9 | 108.36 (15) | C3—C4—H41 | 105.72 |
O3—S1—C8 | 106.78 (15) | C3—C4—H42 | 108.33 |
O3—S1—C9 | 107.55 (15) | C5—C4—H41 | 107.79 |
C8—S1—C9 | 105.74 (18) | C5—C4—H42 | 111.55 |
C1—O1—H1 | 108.52 | H41—C4—H42 | 110.42 |
O1—C1—C2 | 107.6 (3) | C4—C5—H51 | 105.64 |
O1—C1—C6 | 117.1 (3) | C4—C5—H52 | 108.53 |
C2—C1—C6 | 114.0 (3) | C6—C5—H51 | 108.62 |
C2—C1—C8 | 109.3 (3) | C6—C5—H52 | 109.16 |
O1—C1—C8 | 119.4 (3) | H51—C5—H52 | 113.27 |
C6—C1—C8 | 88.6 (3) | C1—C6—H6 | 109.07 |
C1—C2—C21 | 112.3 (4) | C5—C6—H6 | 106.10 |
C3—C2—C21 | 114.5 (4) | C7—C6—H6 | 108.91 |
C1—C2—C3 | 108.6 (4) | C6—C7—H71 | 114.58 |
C2—C3—C4 | 108.7 (5) | C6—C7—H72 | 113.67 |
C3—C4—C5 | 112.9 (5) | C8—C7—H71 | 115.07 |
C4—C5—C6 | 111.6 (4) | C8—C7—H72 | 114.12 |
C1—C6—C7 | 89.3 (3) | H71—C7—H72 | 109.13 |
C5—C6—C7 | 122.9 (3) | S1—C8—H8 | 112.84 |
C1—C6—C5 | 119.4 (4) | C1—C8—H8 | 111.56 |
C6—C7—C8 | 89.3 (3) | C7—C8—H8 | 113.46 |
S1—C8—C1 | 117.3 (2) | C9—C10—H10 | 119.59 |
C1—C8—C7 | 87.2 (3) | C11—C10—H10 | 121.62 |
S1—C8—C7 | 112.1 (3) | C10—C11—H11 | 119.53 |
S1—C9—C10 | 120.2 (3) | C12—C11—H11 | 120.37 |
C10—C9—C14 | 120.6 (3) | C11—C12—H12 | 119.48 |
S1—C9—C14 | 119.2 (3) | C13—C12—H12 | 119.87 |
C9—C10—C11 | 118.8 (3) | C12—C13—H13 | 120.43 |
C10—C11—C12 | 120.1 (4) | C14—C13—H13 | 119.56 |
C11—C12—C13 | 120.7 (3) | C9—C14—H14 | 119.26 |
C12—C13—C14 | 120.0 (4) | C13—C14—H14 | 120.87 |
C9—C14—C13 | 119.8 (3) | C2—C21—H211 | 108.30 |
C1—C2—H2 | 107.39 | C2—C21—H212 | 108.34 |
C3—C2—H2 | 106.38 | C2—C21—H213 | 109.77 |
C21—C2—H2 | 107.26 | H211—C21—H212 | 108.68 |
C2—C3—H31 | 108.03 | H211—C21—H213 | 110.88 |
C2—C3—H32 | 106.93 | H212—C21—H213 | 110.79 |
C4—C3—H31 | 112.27 | | |
| | | |
O2—S1—C8—C1 | 37.6 (3) | C2—C1—C6—C7 | 92.7 (3) |
O2—S1—C8—C7 | −61.0 (3) | C8—C1—C6—C5 | −146.0 (3) |
O3—S1—C8—C1 | 166.6 (2) | O1—C1—C6—C7 | −140.6 (3) |
O3—S1—C8—C7 | 68.0 (2) | C8—C1—C2—C21 | −87.5 (4) |
C9—S1—C8—C1 | −79.0 (3) | O1—C1—C6—C5 | 91.3 (4) |
C9—S1—C8—C7 | −177.7 (2) | C2—C1—C6—C5 | −35.4 (4) |
O2—S1—C9—C10 | −12.3 (4) | C21—C2—C3—C4 | 171.6 (5) |
O2—S1—C9—C14 | 165.9 (3) | C1—C2—C3—C4 | −62.1 (6) |
O3—S1—C9—C10 | −141.0 (3) | C2—C3—C4—C5 | 65.2 (7) |
O3—S1—C9—C14 | 37.2 (3) | C3—C4—C5—C6 | −49.4 (7) |
C8—S1—C9—C10 | 105.2 (3) | C4—C5—C6—C1 | 34.9 (6) |
C8—S1—C9—C14 | −76.6 (3) | C4—C5—C6—C7 | −75.4 (6) |
C8—C1—C2—C3 | 144.8 (4) | C5—C6—C7—C8 | 143.5 (4) |
O1—C1—C2—C3 | −84.0 (4) | C1—C6—C7—C8 | 18.3 (3) |
O1—C1—C2—C21 | 43.7 (4) | C6—C7—C8—S1 | 100.7 (3) |
C6—C1—C2—C3 | 47.5 (5) | C6—C7—C8—C1 | −17.7 (3) |
C6—C1—C2—C21 | 175.2 (3) | S1—C9—C10—C11 | 177.6 (3) |
C8—C1—C6—C7 | −17.9 (3) | C10—C9—C14—C13 | 1.8 (6) |
O1—C1—C8—S1 | 24.9 (4) | C14—C9—C10—C11 | −0.6 (6) |
O1—C1—C8—C7 | 138.4 (3) | S1—C9—C14—C13 | −176.5 (3) |
C2—C1—C8—S1 | 149.4 (3) | C9—C10—C11—C12 | −1.1 (6) |
C2—C1—C8—C7 | −97.1 (3) | C10—C11—C12—C13 | 1.6 (6) |
C6—C1—C8—S1 | −95.7 (3) | C11—C12—C13—C14 | −0.4 (6) |
C6—C1—C8—C7 | 17.8 (3) | C12—C13—C14—C9 | −1.3 (6) |
Symmetry codes: (i) −x+3/2, y+1/2, −z+3/2; (ii) −x+2, −y+1, −z+2; (iii) x+1/2, −y+1/2, z+1/2; (iv) −x+2, −y, −z+2; (v) x+1/2, −y+1/2, z−1/2; (vi) −x+3/2, y−1/2, −z+3/2; (vii) −x+3/2, y−1/2, −z+5/2; (viii) x−1/2, −y+1/2, z−1/2; (ix) x−1/2, −y+1/2, z+1/2; (x) −x+3/2, y+1/2, −z+5/2. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···O2 | 0.96 | 2.44 | 3.036 (4) | 120 |
O1—H1···O2ii | 0.96 | 2.02 | 2.918 (3) | 154 |
C10—H10···O2 | 0.9600 | 2.5500 | 2.935 (5) | 104.00 |
C13—H13···O1vi | 0.9400 | 2.5800 | 3.291 (5) | 132.00 |
C14—H14···O3iv | 0.9500 | 2.5600 | 3.444 (4) | 155.00 |
Symmetry codes: (ii) −x+2, −y+1, −z+2; (iv) −x+2, −y, −z+2; (vi) −x+3/2, y−1/2, −z+3/2. |