Download citation
Download citation
link to html
An ortho­rhom­bic (space group Pbcn) polymorph of the title compound, C18H22O7S2, was obtained from a methanol solution to complement the known monoclinic (space group C2/c) phase. No phase transition has been found between the two systems in the temperature range 120-296 K. The central O atom of the mol­ecule has site symmetry 2.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806018782/hb2051sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806018782/hb2051Isup2.hkl
Contains datablock I

CCDC reference: 610786

Key indicators

  • Single-crystal X-ray study
  • T = 120 K
  • Mean [sigma](C-C)= 0.002 Å
  • R factor = 0.032
  • wR factor = 0.068
  • Data-to-parameter ratio = 16.8

checkCIF/PLATON results

No syntax errors found


No errors found in this datablock

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT-Plus (Bruker, 2001); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXTL-NT (Sheldrick, 2001); program(s) used to refine structure: SHELXTL-NT; molecular graphics: SHELXTL-NT; software used to prepare material for publication: SHELXTL-NT.

3-oxapentane-1,5-diyl bis(p-toluenesulfonate) top
Crystal data top
C18H22O7S2F(000) = 872
Mr = 414.48Dx = 1.438 Mg m3
Orthorhombic, PbcnMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2n 2abCell parameters from 5696 reflections
a = 21.914 (2) Åθ = 2.6–30.5°
b = 5.6447 (6) ŵ = 0.32 mm1
c = 15.4723 (15) ÅT = 120 K
V = 1913.9 (3) Å3Prism, colorless
Z = 40.50 × 0.30 × 0.30 mm
Data collection top
Bruker SMART APEX-II CCD area-detector
diffractometer
2621 independent reflections
Radiation source: fine-focus sealed tube2462 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.019
φ and ω scansθmax = 29.5°, θmin = 3.2°
Absorption correction: multi-scan
(SADABS; Sheldrick, 2003)
h = 2929
Tmin = 0.786, Tmax = 0.911k = 57
17461 measured reflectionsl = 2121
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)] = 0.032Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.068H atoms treated by a mixture of independent and constrained refinement
S = 1.00 w = 1/[σ2(Fo2) + (0.01P)2 + 2.05P]
where P = (Fo2 + 2Fc2)/3
2621 reflections(Δ/σ)max = 0.001
156 parametersΔρmax = 0.34 e Å3
0 restraintsΔρmin = 0.32 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
S10.376986 (14)1.04624 (5)0.439011 (18)0.01910 (8)
O10.42178 (5)1.21603 (17)0.46577 (6)0.0265 (2)
O20.32291 (5)1.12553 (19)0.39664 (6)0.0285 (2)
O30.40668 (4)0.86803 (17)0.37247 (5)0.02069 (18)
O40.50000.7497 (2)0.25000.0265 (3)
C10.30768 (6)0.4320 (2)0.74363 (8)0.0240 (3)
H1A0.32430.50050.79680.036*
H1B0.32390.27170.73580.036*
H1C0.26310.42500.74760.036*
C20.32566 (5)0.5836 (2)0.66780 (7)0.0180 (2)
C30.30823 (6)0.5211 (2)0.58388 (8)0.0195 (2)
H30.2854 (7)0.382 (3)0.5749 (10)0.022 (4)*
C40.32386 (6)0.6608 (2)0.51350 (8)0.0191 (2)
H40.3112 (7)0.614 (3)0.4558 (10)0.025 (4)*
C50.35797 (5)0.8655 (2)0.52725 (7)0.0165 (2)
C60.37583 (6)0.9326 (2)0.60997 (8)0.0189 (2)
H60.3989 (7)1.077 (3)0.6183 (10)0.019 (4)*
C70.35934 (6)0.7912 (2)0.67953 (7)0.0198 (2)
H70.3714 (7)0.838 (3)0.7359 (10)0.025 (4)*
C80.46575 (6)0.7661 (3)0.39581 (8)0.0241 (3)
H8A0.4601 (7)0.680 (3)0.4492 (11)0.027 (4)*
H8B0.4922 (8)0.898 (3)0.4050 (11)0.030 (4)*
C90.48522 (6)0.6077 (3)0.32294 (9)0.0256 (3)
H9A0.5216 (7)0.524 (3)0.3429 (10)0.028 (4)*
H9B0.4522 (7)0.495 (3)0.3069 (10)0.029 (4)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.02380 (15)0.01902 (15)0.01449 (13)0.00181 (11)0.00309 (10)0.00139 (10)
O10.0352 (5)0.0211 (4)0.0233 (4)0.0060 (4)0.0055 (4)0.0009 (4)
O20.0314 (5)0.0323 (5)0.0218 (4)0.0100 (4)0.0013 (4)0.0057 (4)
O30.0219 (4)0.0259 (5)0.0143 (4)0.0027 (4)0.0030 (3)0.0016 (3)
O40.0363 (7)0.0200 (6)0.0232 (6)0.0000.0162 (5)0.000
C10.0297 (6)0.0212 (6)0.0212 (6)0.0012 (5)0.0014 (5)0.0051 (5)
C20.0187 (5)0.0175 (5)0.0176 (5)0.0020 (4)0.0019 (4)0.0009 (4)
C30.0208 (5)0.0164 (5)0.0211 (5)0.0016 (5)0.0001 (4)0.0017 (4)
C40.0217 (5)0.0202 (6)0.0155 (5)0.0002 (4)0.0004 (4)0.0032 (4)
C50.0181 (5)0.0174 (5)0.0142 (5)0.0013 (4)0.0028 (4)0.0000 (4)
C60.0211 (5)0.0186 (6)0.0170 (5)0.0026 (4)0.0010 (4)0.0024 (4)
C70.0233 (5)0.0220 (6)0.0140 (5)0.0016 (5)0.0000 (4)0.0016 (4)
C80.0207 (6)0.0312 (7)0.0203 (6)0.0036 (5)0.0040 (5)0.0015 (5)
C90.0293 (6)0.0230 (6)0.0246 (6)0.0031 (5)0.0114 (5)0.0036 (5)
Geometric parameters (Å, º) top
S1—O21.4263 (10)C3—C41.3874 (17)
S1—O11.4330 (10)C3—H30.940 (16)
S1—O31.5796 (9)C4—C51.3923 (17)
S1—C51.7547 (12)C4—H40.971 (16)
O3—C81.4619 (15)C5—C61.3909 (16)
O4—C9i1.4218 (15)C6—C71.3878 (17)
O4—C91.4218 (15)C6—H60.969 (16)
C1—C21.5047 (17)C7—H70.949 (16)
C1—H1A0.9800C8—C91.5010 (19)
C1—H1B0.9800C8—H8A0.966 (17)
C1—H1C0.9800C8—H8B0.954 (18)
C2—C71.3965 (17)C9—H9A0.976 (17)
C2—C31.3987 (16)C9—H9B0.994 (18)
O2—S1—O1119.47 (6)C5—C4—H4121.2 (10)
O2—S1—O3104.03 (5)C6—C5—C4121.17 (11)
O1—S1—O3109.40 (5)C6—C5—S1119.40 (9)
O2—S1—C5110.05 (6)C4—C5—S1119.41 (9)
O1—S1—C5109.07 (6)C7—C6—C5118.93 (11)
O3—S1—C5103.57 (5)C7—C6—H6121.2 (9)
C8—O3—S1117.02 (8)C5—C6—H6119.9 (9)
C9i—O4—C9111.35 (15)C6—C7—C2121.28 (11)
C2—C1—H1A109.5C6—C7—H7118.6 (10)
C2—C1—H1B109.5C2—C7—H7120.1 (10)
H1A—C1—H1B109.5O3—C8—C9107.50 (11)
C2—C1—H1C109.5O3—C8—H8A107.1 (10)
H1A—C1—H1C109.5C9—C8—H8A112.4 (10)
H1B—C1—H1C109.5O3—C8—H8B105.6 (10)
C7—C2—C3118.47 (11)C9—C8—H8B113.8 (10)
C7—C2—C1120.94 (11)H8A—C8—H8B109.9 (14)
C3—C2—C1120.58 (11)O4—C9—C8108.96 (12)
C4—C3—C2121.18 (11)O4—C9—H9A109.7 (10)
C4—C3—H3119.3 (9)C8—C9—H9A106.4 (10)
C2—C3—H3119.6 (9)O4—C9—H9B109.2 (10)
C3—C4—C5118.97 (11)C8—C9—H9B111.2 (10)
C3—C4—H4119.8 (10)H9A—C9—H9B111.3 (15)
O2—S1—O3—C8176.42 (9)O2—S1—C5—C458.77 (11)
O1—S1—O3—C847.69 (10)O1—S1—C5—C4168.36 (10)
C5—S1—O3—C868.50 (10)O3—S1—C5—C451.94 (11)
C7—C2—C3—C40.05 (18)C4—C5—C6—C70.29 (18)
C1—C2—C3—C4179.21 (12)S1—C5—C6—C7178.53 (10)
C2—C3—C4—C50.56 (18)C5—C6—C7—C20.34 (19)
C3—C4—C5—C60.74 (18)C3—C2—C7—C60.51 (18)
C3—C4—C5—S1178.97 (9)C1—C2—C7—C6179.67 (12)
O2—S1—C5—C6119.49 (10)S1—O3—C8—C9179.00 (9)
O1—S1—C5—C613.38 (12)C9i—O4—C9—C8176.00 (13)
O3—S1—C5—C6129.80 (10)O3—C8—C9—O469.63 (13)
Symmetry code: (i) x+1, y, z+1/2.
 

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