The structure of the title compound, C16H22O3S, shows the phenylsulfonylethyl side chain to be in the equatorial orientation.
Supporting information
CCDC reference: 200779
Key indicators
- Single-crystal X-ray study
- T = 295 K
- Mean (C-C) = 0.006 Å
- R factor = 0.042
- wR factor = 0.125
- Data-to-parameter ratio = 11.6
checkCIF results
No syntax errors found
ADDSYM reports no extra symmetry
Alert Level C:
STRVAL_01
From the CIF: _refine_ls_abs_structure_Flack 0.410
From the CIF: _refine_ls_abs_structure_Flack_su 0.170
Alert C Flack test results are ambiguous.
General Notes
REFLT_03
From the CIF: _diffrn_reflns_theta_max 27.60
From the CIF: _reflns_number_total 2094
Count of symmetry unique reflns 2084
Completeness (_total/calc) 100.48%
TEST3: Check Friedels for noncentro structure
Estimate of Friedel pairs measured 10
Fraction of Friedel pairs measured 0.005
Are heavy atom types Z>Si present yes
WARNING: Large fraction of Friedel related reflns may
be needed to determine absolute structure
0 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
1 Alert Level C = Please check
Data collection: MSC/AFC7 Diffractometer Control Software for Windows
(Molecular Structure Corporation, 1999); cell refinement: MSC/AFC7 Diffractometer Control Software for Windows; data reduction: TEXSAN (Molecular Structure Corporation, 1997-2001); program(s) used to solve structure: TEXSAN; program(s) used to refine structure: TEXSAN and SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 1980-2001) and ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: TEXSAN and PLATON.
Crystal data top
C16H22O3S | F(000) = 632 |
Mr = 294.41 | Dx = 1.263 Mg m−3 |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71069 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 25 reflections |
a = 12.641 (3) Å | θ = 13.0–16.5° |
b = 20.240 (5) Å | µ = 0.21 mm−1 |
c = 6.051 (2) Å | T = 295 K |
V = 1548.2 (7) Å3 | Prismatic, colorless |
Z = 4 | 0.60 × 0.40 × 0.20 mm |
Data collection top
Rigaku AFC-7R diffractometer | Rint = 0.034 |
Radiation source: Rigaku rotating anode | θmax = 27.6°, θmin = 2.6° |
Graphite monochromator | h = −6→16 |
ω scans | k = 0→26 |
2193 measured reflections | l = −3→7 |
2094 independent reflections | 3 standard reflections every 150 reflections |
1316 reflections with I > 2σ(I) | intensity decay: 2.2% |
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)] = 0.042 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.125 | H-atom parameters constrained |
S = 0.99 | w = 1/[σ2(Fo2) + (0.0606P)2] where P = (Fo2 + 2Fc2)/3 |
2094 reflections | (Δ/σ)max < 0.001 |
181 parameters | Δρmax = 0.23 e Å−3 |
0 restraints | Δρmin = −0.20 e Å−3 |
Special details top
Experimental. The scan width was (1.26 + 0.30tanθ)° with an ω scan speed of 16° 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 | 0.60529 (8) | −0.04661 (5) | 0.91520 (18) | 0.0460 (3) | |
O1 | 0.4166 (2) | 0.12558 (13) | 0.8449 (5) | 0.0606 (10) | |
O2 | 0.6748 (2) | −0.07620 (14) | 0.7563 (6) | 0.0638 (10) | |
O3 | 0.6197 (2) | −0.06300 (15) | 1.1454 (5) | 0.0643 (11) | |
C1 | 0.4737 (3) | 0.16339 (17) | 0.7485 (7) | 0.0354 (11) | |
C2 | 0.5775 (3) | 0.14122 (15) | 0.6423 (6) | 0.0334 (10) | |
C3 | 0.5724 (3) | 0.16031 (17) | 0.3937 (6) | 0.0434 (11) | |
C4 | 0.5432 (4) | 0.2325 (2) | 0.3540 (7) | 0.0540 (14) | |
C5 | 0.4401 (4) | 0.25006 (19) | 0.4665 (7) | 0.0489 (11) | |
C6 | 0.4425 (3) | 0.23502 (18) | 0.7168 (6) | 0.0400 (12) | |
C7 | 0.6711 (3) | 0.17573 (18) | 0.7531 (7) | 0.0439 (11) | |
C8 | 0.3388 (3) | 0.2526 (2) | 0.8303 (8) | 0.0617 (16) | |
C9 | 0.5895 (3) | 0.06534 (16) | 0.6564 (6) | 0.0389 (10) | |
C10 | 0.6133 (3) | 0.04027 (16) | 0.8895 (6) | 0.0413 (10) | |
C11 | 0.4736 (3) | −0.06682 (18) | 0.8418 (7) | 0.0443 (12) | |
C12 | 0.4514 (4) | −0.0935 (2) | 0.6374 (9) | 0.0617 (17) | |
C13 | 0.3470 (5) | −0.1094 (3) | 0.5885 (9) | 0.0763 (19) | |
C14 | 0.2680 (4) | −0.0992 (3) | 0.7376 (12) | 0.085 (2) | |
C15 | 0.2906 (4) | −0.0725 (3) | 0.9435 (11) | 0.086 (2) | |
C16 | 0.3951 (4) | −0.0568 (2) | 0.9956 (7) | 0.0663 (16) | |
H12 | 0.50600 | −0.10080 | 0.53260 | 0.0740* | |
H13 | 0.33060 | −0.12780 | 0.44830 | 0.0920* | |
H14 | 0.19730 | −0.11050 | 0.70070 | 0.1020* | |
H15 | 0.23550 | −0.06500 | 1.04740 | 0.1030* | |
H16 | 0.41200 | −0.03940 | 1.13690 | 0.0790* | |
H31 | 0.52100 | 0.13330 | 0.32370 | 0.0520* | |
H32 | 0.63980 | 0.15230 | 0.32950 | 0.0520* | |
H41 | 0.59780 | 0.25990 | 0.41080 | 0.0650* | |
H42 | 0.53610 | 0.23980 | 0.19960 | 0.0650* | |
H51 | 0.38470 | 0.22520 | 0.40070 | 0.0580* | |
H52 | 0.42700 | 0.29590 | 0.44630 | 0.0580* | |
H61 | 0.49640 | 0.26160 | 0.78070 | 0.0480* | |
H71 | 0.66560 | 0.17100 | 0.90890 | 0.0530* | |
H72 | 0.73520 | 0.15630 | 0.70370 | 0.0530* | |
H73 | 0.67050 | 0.22130 | 0.71570 | 0.0530* | |
H81 | 0.34790 | 0.25030 | 0.98600 | 0.0740* | |
H82 | 0.28550 | 0.22240 | 0.78600 | 0.0740* | |
H83 | 0.31860 | 0.29620 | 0.78990 | 0.0740* | |
H91 | 0.52540 | 0.04560 | 0.60750 | 0.0470* | |
H92 | 0.64570 | 0.05230 | 0.56180 | 0.0470* | |
H101 | 0.56390 | 0.05960 | 0.98860 | 0.0500* | |
H102 | 0.68280 | 0.05370 | 0.92850 | 0.0500* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
S1 | 0.0443 (4) | 0.0359 (4) | 0.0577 (6) | 0.0044 (4) | −0.0083 (5) | 0.0048 (5) |
O1 | 0.0467 (16) | 0.0522 (15) | 0.083 (2) | 0.0064 (13) | 0.0220 (16) | 0.0197 (15) |
O2 | 0.0570 (17) | 0.0433 (15) | 0.091 (2) | 0.0123 (14) | 0.0035 (19) | −0.0044 (17) |
O3 | 0.0670 (19) | 0.0667 (19) | 0.0592 (17) | −0.0015 (16) | −0.0223 (17) | 0.0266 (15) |
C1 | 0.0324 (18) | 0.040 (2) | 0.0337 (18) | 0.0003 (15) | −0.0021 (17) | 0.0003 (17) |
C2 | 0.0364 (17) | 0.0343 (16) | 0.0295 (17) | 0.0014 (15) | −0.0003 (15) | −0.0006 (15) |
C3 | 0.050 (2) | 0.0442 (19) | 0.036 (2) | 0.0026 (17) | 0.0050 (19) | 0.0002 (17) |
C4 | 0.065 (3) | 0.054 (2) | 0.043 (2) | 0.004 (2) | 0.009 (2) | 0.011 (2) |
C5 | 0.057 (2) | 0.0406 (19) | 0.049 (2) | 0.0077 (19) | −0.003 (2) | 0.0086 (18) |
C6 | 0.040 (2) | 0.039 (2) | 0.041 (2) | 0.0061 (16) | 0.0061 (18) | 0.0026 (17) |
C7 | 0.0367 (19) | 0.042 (2) | 0.053 (2) | −0.0049 (16) | 0.006 (2) | −0.0085 (19) |
C8 | 0.057 (3) | 0.057 (2) | 0.071 (3) | 0.025 (2) | 0.020 (2) | 0.011 (3) |
C9 | 0.0380 (18) | 0.0347 (16) | 0.0441 (19) | 0.0046 (14) | 0.0002 (17) | −0.0057 (16) |
C10 | 0.0403 (17) | 0.0346 (16) | 0.049 (2) | 0.0043 (16) | −0.007 (2) | −0.0001 (17) |
C11 | 0.045 (2) | 0.042 (2) | 0.046 (2) | −0.0028 (17) | −0.007 (2) | 0.0082 (19) |
C12 | 0.069 (3) | 0.052 (3) | 0.064 (3) | −0.013 (2) | −0.008 (3) | −0.003 (2) |
C13 | 0.094 (4) | 0.069 (3) | 0.066 (3) | −0.029 (3) | −0.030 (3) | 0.010 (3) |
C14 | 0.062 (3) | 0.088 (4) | 0.106 (5) | −0.031 (3) | −0.030 (4) | 0.019 (4) |
C15 | 0.055 (3) | 0.107 (4) | 0.096 (4) | −0.018 (3) | 0.002 (3) | 0.023 (4) |
C16 | 0.054 (2) | 0.081 (3) | 0.064 (3) | −0.017 (3) | −0.005 (2) | 0.000 (2) |
Geometric parameters (Å, º) top
S1—O2 | 1.434 (3) | C3—H32 | 0.9503 |
S1—O3 | 1.443 (3) | C4—H41 | 0.9498 |
S1—C10 | 1.768 (3) | C4—H42 | 0.9501 |
S1—C11 | 1.771 (4) | C5—H51 | 0.9498 |
O1—C1 | 1.203 (5) | C5—H52 | 0.9504 |
C1—C2 | 1.528 (5) | C6—H61 | 0.9504 |
C1—C6 | 1.515 (5) | C7—H71 | 0.9501 |
C2—C3 | 1.554 (5) | C7—H72 | 0.9490 |
C2—C7 | 1.529 (5) | C7—H73 | 0.9497 |
C2—C9 | 1.546 (4) | C8—H81 | 0.9503 |
C3—C4 | 1.526 (5) | C8—H82 | 0.9484 |
C4—C5 | 1.513 (7) | C8—H83 | 0.9506 |
C5—C6 | 1.545 (6) | C9—H91 | 0.9507 |
C6—C8 | 1.522 (6) | C9—H92 | 0.9498 |
C9—C10 | 1.529 (5) | C10—H101 | 0.9501 |
C11—C12 | 1.378 (7) | C10—H102 | 0.9494 |
C11—C16 | 1.375 (6) | C12—H12 | 0.9489 |
C12—C13 | 1.390 (8) | C13—H13 | 0.9494 |
C13—C14 | 1.362 (9) | C14—H14 | 0.9492 |
C14—C15 | 1.388 (10) | C15—H15 | 0.9505 |
C15—C16 | 1.395 (7) | C16—H16 | 0.9491 |
C3—H31 | 0.9489 | | |
| | | |
O1···C10 | 3.039 (5) | H32···O2iv | 2.8392 |
O1···C14i | 3.373 (7) | H32···H83x | 2.5917 |
O1···H81 | 2.8027 | H41···C7 | 2.8374 |
O1···H91 | 2.5643 | H41···H61 | 2.5795 |
O1···H101 | 2.4508 | H41···H73 | 2.2043 |
O1···H82 | 2.5911 | H51···H31 | 2.5779 |
O1···H14i | 2.6079 | H52···H83 | 2.4901 |
O1···H15ii | 2.9053 | H61···C7 | 2.8152 |
O2···H12 | 2.5755 | H61···H41 | 2.5795 |
O2···H92 | 2.8783 | H61···H73 | 2.3798 |
O2···H32iii | 2.8392 | H61···C12xi | 3.0467 |
O2···H102iv | 2.7170 | H71···C10 | 2.7298 |
O2···H83v | 2.5990 | H71···H32vi | 2.5936 |
O3···H12vi | 2.8532 | H71···H102 | 2.3870 |
O3···H16 | 2.6691 | H72···C10 | 3.0255 |
O3···H72iii | 2.6561 | H72···H32 | 2.5667 |
C7···C8vii | 3.599 (6) | H72···H92 | 2.5393 |
C8···C7viii | 3.599 (6) | H72···H102 | 2.5693 |
C10···O1 | 3.039 (5) | H72···O3iv | 2.6561 |
C14···O1ii | 3.373 (7) | H73···C4 | 2.7260 |
C1···H101 | 2.7971 | H73···C6 | 2.8955 |
C4···H73 | 2.7260 | H73···H41 | 2.2043 |
C6···H73 | 2.8955 | H73···H61 | 2.3798 |
C7···H61 | 2.8152 | H81···O1 | 2.8027 |
C7···H101 | 3.0646 | H82···O1 | 2.5911 |
C7···H41 | 2.8374 | H83···H52 | 2.4901 |
C7···H102 | 2.6923 | H83···H32xii | 2.5917 |
C10···H71 | 2.7298 | H83···O2xi | 2.5990 |
C10···H72 | 3.0255 | H91···O1 | 2.5643 |
C11···H91 | 2.7597 | H91···C11 | 2.7597 |
C12···H91 | 2.9722 | H91···C12 | 2.9722 |
C12···H61v | 3.0467 | H91···H31 | 2.4704 |
H12···O2 | 2.5755 | H92···O2 | 2.8783 |
H12···O3ix | 2.8532 | H92···H32 | 2.4654 |
H14···O1ii | 2.6079 | H92···H72 | 2.5393 |
H15···O1i | 2.9053 | H101···O1 | 2.4508 |
H16···O3 | 2.6691 | H101···C1 | 2.7971 |
H31···H51 | 2.5779 | H101···C7 | 3.0646 |
H31···H91 | 2.4704 | H101···H31vi | 2.5750 |
H31···H101ix | 2.5750 | H102···C7 | 2.6923 |
H32···H71ix | 2.5936 | H102···H71 | 2.3870 |
H32···H72 | 2.5667 | H102···H72 | 2.5693 |
H32···H92 | 2.4654 | H102···O2iii | 2.7170 |
| | | |
O2—S1—O3 | 118.29 (18) | C4—C5—H51 | 108.79 |
O2—S1—C10 | 108.75 (18) | C4—C5—H52 | 108.76 |
O2—S1—C11 | 108.15 (18) | C6—C5—H51 | 108.72 |
O3—S1—C10 | 107.83 (18) | C6—C5—H52 | 108.77 |
O3—S1—C11 | 107.91 (18) | H51—C5—H52 | 109.56 |
C10—S1—C11 | 105.16 (18) | C1—C6—H61 | 107.68 |
O1—C1—C2 | 122.2 (3) | C5—C6—H61 | 107.54 |
O1—C1—C6 | 120.9 (3) | C8—C6—H61 | 107.55 |
C2—C1—C6 | 116.8 (3) | C2—C7—H71 | 109.42 |
C1—C2—C3 | 107.4 (3) | C2—C7—H72 | 109.47 |
C1—C2—C7 | 110.2 (3) | C2—C7—H73 | 109.45 |
C1—C2—C9 | 110.7 (3) | H71—C7—H72 | 109.47 |
C3—C2—C7 | 110.1 (3) | H71—C7—H73 | 109.49 |
C3—C2—C9 | 107.7 (3) | H72—C7—H73 | 109.52 |
C7—C2—C9 | 110.7 (3) | C6—C8—H81 | 109.37 |
C2—C3—C4 | 113.6 (3) | C6—C8—H82 | 109.49 |
C3—C4—C5 | 111.3 (3) | C6—C8—H83 | 109.41 |
C4—C5—C6 | 112.2 (4) | H81—C8—H82 | 109.55 |
C1—C6—C5 | 108.5 (3) | H81—C8—H83 | 109.45 |
C1—C6—C8 | 113.0 (3) | H82—C8—H83 | 109.56 |
C5—C6—C8 | 112.3 (3) | C2—C9—H91 | 108.47 |
C2—C9—C10 | 113.6 (3) | C2—C9—H92 | 108.44 |
S1—C10—C9 | 113.6 (2) | C10—C9—H91 | 108.38 |
S1—C11—C12 | 120.5 (3) | C10—C9—H92 | 108.46 |
S1—C11—C16 | 118.3 (3) | H91—C9—H92 | 109.46 |
C12—C11—C16 | 121.2 (4) | S1—C10—H101 | 108.44 |
C11—C12—C13 | 118.4 (5) | S1—C10—H102 | 108.41 |
C12—C13—C14 | 121.3 (5) | C9—C10—H101 | 108.44 |
C13—C14—C15 | 120.2 (5) | C9—C10—H102 | 108.44 |
C14—C15—C16 | 119.1 (5) | H101—C10—H102 | 109.48 |
C11—C16—C15 | 119.8 (4) | C11—C12—H12 | 120.84 |
C2—C3—H31 | 108.49 | C13—C12—H12 | 120.81 |
C2—C3—H32 | 108.42 | C12—C13—H13 | 119.23 |
C4—C3—H31 | 108.40 | C14—C13—H13 | 119.43 |
C4—C3—H32 | 108.41 | C13—C14—H14 | 119.88 |
H31—C3—H32 | 109.46 | C15—C14—H14 | 119.92 |
C3—C4—H41 | 109.05 | C14—C15—H15 | 120.34 |
C3—C4—H42 | 109.06 | C16—C15—H15 | 120.54 |
C5—C4—H41 | 109.03 | C11—C16—H16 | 120.12 |
C5—C4—H42 | 108.94 | C15—C16—H16 | 120.09 |
H41—C4—H42 | 109.49 | | |
| | | |
O2—S1—C10—C9 | 55.8 (3) | C1—C2—C9—C10 | −72.2 (4) |
O3—S1—C10—C9 | −174.8 (3) | C1—C2—C3—C4 | 51.7 (4) |
C11—S1—C10—C9 | −59.9 (3) | C7—C2—C3—C4 | −68.3 (4) |
O2—S1—C11—C12 | −12.9 (4) | C9—C2—C3—C4 | 170.9 (3) |
O2—S1—C11—C16 | 165.5 (3) | C7—C2—C9—C10 | 50.4 (4) |
O3—S1—C11—C12 | −141.9 (3) | C3—C2—C9—C10 | 170.8 (3) |
O3—S1—C11—C16 | 36.4 (4) | C2—C3—C4—C5 | −55.3 (5) |
C10—S1—C11—C12 | 103.2 (3) | C3—C4—C5—C6 | 55.8 (4) |
C10—S1—C11—C16 | −78.5 (3) | C4—C5—C6—C8 | −179.9 (3) |
O1—C1—C6—C5 | −121.5 (4) | C4—C5—C6—C1 | −54.3 (4) |
C6—C1—C2—C7 | 66.3 (4) | C2—C9—C10—S1 | 170.1 (3) |
C6—C1—C2—C9 | −170.9 (3) | S1—C11—C12—C13 | 179.1 (4) |
C2—C1—C6—C8 | −179.4 (3) | C12—C11—C16—C15 | −1.4 (6) |
O1—C1—C2—C7 | −116.8 (4) | C16—C11—C12—C13 | 0.8 (6) |
O1—C1—C2—C9 | 6.0 (5) | S1—C11—C16—C15 | −179.7 (4) |
C6—C1—C2—C3 | −53.6 (4) | C11—C12—C13—C14 | −0.1 (8) |
O1—C1—C2—C3 | 123.3 (4) | C12—C13—C14—C15 | −0.1 (9) |
O1—C1—C6—C8 | 3.7 (5) | C13—C14—C15—C16 | −0.5 (9) |
C2—C1—C6—C5 | 55.4 (4) | C14—C15—C16—C11 | 1.2 (8) |
Symmetry codes: (i) −x+1/2, −y, z+1/2; (ii) −x+1/2, −y, z−1/2; (iii) −x+3/2, −y, z+1/2; (iv) −x+3/2, −y, z−1/2; (v) −x+1, y−1/2, −z+3/2; (vi) x, y, z+1; (vii) x+1/2, −y+1/2, −z+2; (viii) x−1/2, −y+1/2, −z+2; (ix) x, y, z−1; (x) x+1/2, −y+1/2, −z+1; (xi) −x+1, y+1/2, −z+3/2; (xii) x−1/2, −y+1/2, −z+1. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C12—H12···O2 | 0.95 | 2.58 | 2.935 (6) | 103 |
C8—H83···O2xi | 0.95 | 2.60 | 3.509 (5) | 160 |
C10—H101···O1 | 0.95 | 2.45 | 3.039 (5) | 120 |
Symmetry code: (xi) −x+1, y+1/2, −z+3/2. |