Download citation
Download citation
link to html
The structure of the title compound, C16H22O3S, shows the phenyl­sulfonyl­ethyl side chain to be in the equatorial orientation.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802019037/tk6080sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536802019037/tk6080Isup2.hkl
Contains datablock I

CCDC reference: 200779

Key indicators

  • Single-crystal X-ray study
  • T = 295 K
  • Mean [sigma](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


Yellow Alert 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

Computing details top

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.

(I) top
Crystal data top
C16H22O3SF(000) = 632
Mr = 294.41Dx = 1.263 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71069 Å
Hall symbol: P 2ac 2abCell parameters from 25 reflections
a = 12.641 (3) Åθ = 13.0–16.5°
b = 20.240 (5) ŵ = 0.21 mm1
c = 6.051 (2) ÅT = 295 K
V = 1548.2 (7) Å3Prismatic, colorless
Z = 40.60 × 0.40 × 0.20 mm
Data collection top
Rigaku AFC-7R
diffractometer
Rint = 0.034
Radiation source: Rigaku rotating anodeθmax = 27.6°, θmin = 2.6°
Graphite monochromatorh = 616
ω scansk = 026
2193 measured reflectionsl = 37
2094 independent reflections3 standard reflections every 150 reflections
1316 reflections with I > 2σ(I) intensity decay: 2.2%
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)] = 0.042Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.125H-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 parametersΔρmax = 0.23 e Å3
0 restraintsΔρmin = 0.20 e Å3
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
xyzUiso*/Ueq
S10.60529 (8)0.04661 (5)0.91520 (18)0.0460 (3)
O10.4166 (2)0.12558 (13)0.8449 (5)0.0606 (10)
O20.6748 (2)0.07620 (14)0.7563 (6)0.0638 (10)
O30.6197 (2)0.06300 (15)1.1454 (5)0.0643 (11)
C10.4737 (3)0.16339 (17)0.7485 (7)0.0354 (11)
C20.5775 (3)0.14122 (15)0.6423 (6)0.0334 (10)
C30.5724 (3)0.16031 (17)0.3937 (6)0.0434 (11)
C40.5432 (4)0.2325 (2)0.3540 (7)0.0540 (14)
C50.4401 (4)0.25006 (19)0.4665 (7)0.0489 (11)
C60.4425 (3)0.23502 (18)0.7168 (6)0.0400 (12)
C70.6711 (3)0.17573 (18)0.7531 (7)0.0439 (11)
C80.3388 (3)0.2526 (2)0.8303 (8)0.0617 (16)
C90.5895 (3)0.06534 (16)0.6564 (6)0.0389 (10)
C100.6133 (3)0.04027 (16)0.8895 (6)0.0413 (10)
C110.4736 (3)0.06682 (18)0.8418 (7)0.0443 (12)
C120.4514 (4)0.0935 (2)0.6374 (9)0.0617 (17)
C130.3470 (5)0.1094 (3)0.5885 (9)0.0763 (19)
C140.2680 (4)0.0992 (3)0.7376 (12)0.085 (2)
C150.2906 (4)0.0725 (3)0.9435 (11)0.086 (2)
C160.3951 (4)0.0568 (2)0.9956 (7)0.0663 (16)
H120.506000.100800.532600.0740*
H130.330600.127800.448300.0920*
H140.197300.110500.700700.1020*
H150.235500.065001.047400.1030*
H160.412000.039401.136900.0790*
H310.521000.133300.323700.0520*
H320.639800.152300.329500.0520*
H410.597800.259900.410800.0650*
H420.536100.239800.199600.0650*
H510.384700.225200.400700.0580*
H520.427000.295900.446300.0580*
H610.496400.261600.780700.0480*
H710.665600.171000.908900.0530*
H720.735200.156300.703700.0530*
H730.670500.221300.715700.0530*
H810.347900.250300.986000.0740*
H820.285500.222400.786000.0740*
H830.318600.296200.789900.0740*
H910.525400.045600.607500.0470*
H920.645700.052300.561800.0470*
H1010.563900.059600.988600.0500*
H1020.682800.053700.928500.0500*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0443 (4)0.0359 (4)0.0577 (6)0.0044 (4)0.0083 (5)0.0048 (5)
O10.0467 (16)0.0522 (15)0.083 (2)0.0064 (13)0.0220 (16)0.0197 (15)
O20.0570 (17)0.0433 (15)0.091 (2)0.0123 (14)0.0035 (19)0.0044 (17)
O30.0670 (19)0.0667 (19)0.0592 (17)0.0015 (16)0.0223 (17)0.0266 (15)
C10.0324 (18)0.040 (2)0.0337 (18)0.0003 (15)0.0021 (17)0.0003 (17)
C20.0364 (17)0.0343 (16)0.0295 (17)0.0014 (15)0.0003 (15)0.0006 (15)
C30.050 (2)0.0442 (19)0.036 (2)0.0026 (17)0.0050 (19)0.0002 (17)
C40.065 (3)0.054 (2)0.043 (2)0.004 (2)0.009 (2)0.011 (2)
C50.057 (2)0.0406 (19)0.049 (2)0.0077 (19)0.003 (2)0.0086 (18)
C60.040 (2)0.039 (2)0.041 (2)0.0061 (16)0.0061 (18)0.0026 (17)
C70.0367 (19)0.042 (2)0.053 (2)0.0049 (16)0.006 (2)0.0085 (19)
C80.057 (3)0.057 (2)0.071 (3)0.025 (2)0.020 (2)0.011 (3)
C90.0380 (18)0.0347 (16)0.0441 (19)0.0046 (14)0.0002 (17)0.0057 (16)
C100.0403 (17)0.0346 (16)0.049 (2)0.0043 (16)0.007 (2)0.0001 (17)
C110.045 (2)0.042 (2)0.046 (2)0.0028 (17)0.007 (2)0.0082 (19)
C120.069 (3)0.052 (3)0.064 (3)0.013 (2)0.008 (3)0.003 (2)
C130.094 (4)0.069 (3)0.066 (3)0.029 (3)0.030 (3)0.010 (3)
C140.062 (3)0.088 (4)0.106 (5)0.031 (3)0.030 (4)0.019 (4)
C150.055 (3)0.107 (4)0.096 (4)0.018 (3)0.002 (3)0.023 (4)
C160.054 (2)0.081 (3)0.064 (3)0.017 (3)0.005 (2)0.000 (2)
Geometric parameters (Å, º) top
S1—O21.434 (3)C3—H320.9503
S1—O31.443 (3)C4—H410.9498
S1—C101.768 (3)C4—H420.9501
S1—C111.771 (4)C5—H510.9498
O1—C11.203 (5)C5—H520.9504
C1—C21.528 (5)C6—H610.9504
C1—C61.515 (5)C7—H710.9501
C2—C31.554 (5)C7—H720.9490
C2—C71.529 (5)C7—H730.9497
C2—C91.546 (4)C8—H810.9503
C3—C41.526 (5)C8—H820.9484
C4—C51.513 (7)C8—H830.9506
C5—C61.545 (6)C9—H910.9507
C6—C81.522 (6)C9—H920.9498
C9—C101.529 (5)C10—H1010.9501
C11—C121.378 (7)C10—H1020.9494
C11—C161.375 (6)C12—H120.9489
C12—C131.390 (8)C13—H130.9494
C13—C141.362 (9)C14—H140.9492
C14—C151.388 (10)C15—H150.9505
C15—C161.395 (7)C16—H160.9491
C3—H310.9489
O1···C103.039 (5)H32···O2iv2.8392
O1···C14i3.373 (7)H32···H83x2.5917
O1···H812.8027H41···C72.8374
O1···H912.5643H41···H612.5795
O1···H1012.4508H41···H732.2043
O1···H822.5911H51···H312.5779
O1···H14i2.6079H52···H832.4901
O1···H15ii2.9053H61···C72.8152
O2···H122.5755H61···H412.5795
O2···H922.8783H61···H732.3798
O2···H32iii2.8392H61···C12xi3.0467
O2···H102iv2.7170H71···C102.7298
O2···H83v2.5990H71···H32vi2.5936
O3···H12vi2.8532H71···H1022.3870
O3···H162.6691H72···C103.0255
O3···H72iii2.6561H72···H322.5667
C7···C8vii3.599 (6)H72···H922.5393
C8···C7viii3.599 (6)H72···H1022.5693
C10···O13.039 (5)H72···O3iv2.6561
C14···O1ii3.373 (7)H73···C42.7260
C1···H1012.7971H73···C62.8955
C4···H732.7260H73···H412.2043
C6···H732.8955H73···H612.3798
C7···H612.8152H81···O12.8027
C7···H1013.0646H82···O12.5911
C7···H412.8374H83···H522.4901
C7···H1022.6923H83···H32xii2.5917
C10···H712.7298H83···O2xi2.5990
C10···H723.0255H91···O12.5643
C11···H912.7597H91···C112.7597
C12···H912.9722H91···C122.9722
C12···H61v3.0467H91···H312.4704
H12···O22.5755H92···O22.8783
H12···O3ix2.8532H92···H322.4654
H14···O1ii2.6079H92···H722.5393
H15···O1i2.9053H101···O12.4508
H16···O32.6691H101···C12.7971
H31···H512.5779H101···C73.0646
H31···H912.4704H101···H31vi2.5750
H31···H101ix2.5750H102···C72.6923
H32···H71ix2.5936H102···H712.3870
H32···H722.5667H102···H722.5693
H32···H922.4654H102···O2iii2.7170
O2—S1—O3118.29 (18)C4—C5—H51108.79
O2—S1—C10108.75 (18)C4—C5—H52108.76
O2—S1—C11108.15 (18)C6—C5—H51108.72
O3—S1—C10107.83 (18)C6—C5—H52108.77
O3—S1—C11107.91 (18)H51—C5—H52109.56
C10—S1—C11105.16 (18)C1—C6—H61107.68
O1—C1—C2122.2 (3)C5—C6—H61107.54
O1—C1—C6120.9 (3)C8—C6—H61107.55
C2—C1—C6116.8 (3)C2—C7—H71109.42
C1—C2—C3107.4 (3)C2—C7—H72109.47
C1—C2—C7110.2 (3)C2—C7—H73109.45
C1—C2—C9110.7 (3)H71—C7—H72109.47
C3—C2—C7110.1 (3)H71—C7—H73109.49
C3—C2—C9107.7 (3)H72—C7—H73109.52
C7—C2—C9110.7 (3)C6—C8—H81109.37
C2—C3—C4113.6 (3)C6—C8—H82109.49
C3—C4—C5111.3 (3)C6—C8—H83109.41
C4—C5—C6112.2 (4)H81—C8—H82109.55
C1—C6—C5108.5 (3)H81—C8—H83109.45
C1—C6—C8113.0 (3)H82—C8—H83109.56
C5—C6—C8112.3 (3)C2—C9—H91108.47
C2—C9—C10113.6 (3)C2—C9—H92108.44
S1—C10—C9113.6 (2)C10—C9—H91108.38
S1—C11—C12120.5 (3)C10—C9—H92108.46
S1—C11—C16118.3 (3)H91—C9—H92109.46
C12—C11—C16121.2 (4)S1—C10—H101108.44
C11—C12—C13118.4 (5)S1—C10—H102108.41
C12—C13—C14121.3 (5)C9—C10—H101108.44
C13—C14—C15120.2 (5)C9—C10—H102108.44
C14—C15—C16119.1 (5)H101—C10—H102109.48
C11—C16—C15119.8 (4)C11—C12—H12120.84
C2—C3—H31108.49C13—C12—H12120.81
C2—C3—H32108.42C12—C13—H13119.23
C4—C3—H31108.40C14—C13—H13119.43
C4—C3—H32108.41C13—C14—H14119.88
H31—C3—H32109.46C15—C14—H14119.92
C3—C4—H41109.05C14—C15—H15120.34
C3—C4—H42109.06C16—C15—H15120.54
C5—C4—H41109.03C11—C16—H16120.12
C5—C4—H42108.94C15—C16—H16120.09
H41—C4—H42109.49
O2—S1—C10—C955.8 (3)C1—C2—C9—C1072.2 (4)
O3—S1—C10—C9174.8 (3)C1—C2—C3—C451.7 (4)
C11—S1—C10—C959.9 (3)C7—C2—C3—C468.3 (4)
O2—S1—C11—C1212.9 (4)C9—C2—C3—C4170.9 (3)
O2—S1—C11—C16165.5 (3)C7—C2—C9—C1050.4 (4)
O3—S1—C11—C12141.9 (3)C3—C2—C9—C10170.8 (3)
O3—S1—C11—C1636.4 (4)C2—C3—C4—C555.3 (5)
C10—S1—C11—C12103.2 (3)C3—C4—C5—C655.8 (4)
C10—S1—C11—C1678.5 (3)C4—C5—C6—C8179.9 (3)
O1—C1—C6—C5121.5 (4)C4—C5—C6—C154.3 (4)
C6—C1—C2—C766.3 (4)C2—C9—C10—S1170.1 (3)
C6—C1—C2—C9170.9 (3)S1—C11—C12—C13179.1 (4)
C2—C1—C6—C8179.4 (3)C12—C11—C16—C151.4 (6)
O1—C1—C2—C7116.8 (4)C16—C11—C12—C130.8 (6)
O1—C1—C2—C96.0 (5)S1—C11—C16—C15179.7 (4)
C6—C1—C2—C353.6 (4)C11—C12—C13—C140.1 (8)
O1—C1—C2—C3123.3 (4)C12—C13—C14—C150.1 (9)
O1—C1—C6—C83.7 (5)C13—C14—C15—C160.5 (9)
C2—C1—C6—C555.4 (4)C14—C15—C16—C111.2 (8)
Symmetry codes: (i) x+1/2, y, z+1/2; (ii) x+1/2, y, z1/2; (iii) x+3/2, y, z+1/2; (iv) x+3/2, y, z1/2; (v) x+1, y1/2, z+3/2; (vi) x, y, z+1; (vii) x+1/2, y+1/2, z+2; (viii) x1/2, y+1/2, z+2; (ix) x, y, z1; (x) x+1/2, y+1/2, z+1; (xi) x+1, y+1/2, z+3/2; (xii) x1/2, y+1/2, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C12—H12···O20.952.582.935 (6)103
C8—H83···O2xi0.952.603.509 (5)160
C10—H101···O10.952.453.039 (5)120
Symmetry code: (xi) x+1, y+1/2, z+3/2.
 

Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds