Buy article online - an online subscription or single-article purchase is required to access this article.
Download citation
Download citation
link to html
The title compound, C23H22O2S2, consists of an m-xyl­ene moiety symmetrically linked by phenoxymethyl groups, which are bridged by a methanedi­thiol unit. The two benzene rings at the dithio end of the molecule are almost perpendicular to each other [87.1 (1)°]. The crystal packing is stabilized by C—H...π and weak π...π interactions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803020129/bt6351sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536803020129/bt6351Isup2.hkl
Contains datablock I

CCDC reference: 226965

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.041
  • wR factor = 0.127
  • Data-to-parameter ratio = 23.8

checkCIF/PLATON results

No syntax errors found


No errors found in this datablock

Computing details top

Data collection: CAD-4 EXPRESS (Enraf Nonius, 1994); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ZORTEP (Zsolnai, 1997) and PLATON (Spek, 1990); software used to prepare material for publication: SHELXL97 and PARST (Nardelli, 1995).

9, 17-Dioxa-1,3-dithiatetracyclo[18. 2. 2. 223, 24. 125] heptacosan-5, 7, 11,13, 15 (25), 18, 20, 23, 26 nonene top
Crystal data top
C23H22O2S2Z = 2
Mr = 394.53F(000) = 416
Triclinic, P1Dx = 1.306 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 9.995 (5) ÅCell parameters from 25 reflections
b = 10.372 (7) Åθ = 1.8–12.6°
c = 10.508 (5) ŵ = 0.28 mm1
α = 101.84 (5)°T = 293 K
β = 91.14 (5)°Block, colourless
γ = 109.01 (5)°0.46 × 0.29 × 0.28 mm
V = 1003.5 (10) Å3
Data collection top
Enraf Nonius FR590
diffractometer
Rint = 0.023
Radiation source: fine-focus sealed tubeθmax = 30.0°, θmin = 2.0°
Graphite monochromatorh = 1413
non–profiled w/2θ scansk = 014
6133 measured reflectionsl = 1414
5832 independent reflections3 standard reflections every 200 reflections
3032 reflections with I > 2σ(I) intensity decay: 3%
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.042H-atom parameters constrained
wR(F2) = 0.127 w = 1/[σ2(Fo2) + (0.0631P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.02(Δ/σ)max = 0.001
5832 reflectionsΔρmax = 0.21 e Å3
245 parametersΔρmin = 0.26 e Å3
0 restraintsExtinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.070 (4)
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
S10.37039 (5)0.18755 (6)0.59690 (6)0.06067 (18)
S20.21438 (6)0.38690 (6)0.52576 (5)0.05563 (17)
O10.08204 (13)0.39596 (13)0.97943 (12)0.0515 (3)
O20.42171 (14)0.02889 (15)0.82650 (17)0.0660 (4)
C10.33671 (18)0.33670 (19)0.93297 (18)0.0441 (4)
H10.28810.30511.00130.053*
C20.43220 (18)0.27419 (19)0.87843 (18)0.0437 (4)
C30.50688 (19)0.3252 (2)0.77861 (19)0.0510 (5)
H30.57120.28500.74020.061*
C40.4858 (2)0.4351 (2)0.7366 (2)0.0547 (5)
H40.53760.47010.67130.066*
C50.3879 (2)0.4939 (2)0.79078 (19)0.0509 (5)
H50.37360.56720.76080.061*
C60.31161 (18)0.44420 (18)0.88901 (18)0.0429 (4)
C70.2003 (2)0.5014 (2)0.9476 (2)0.0535 (5)
H7A0.24300.57301.02600.064*
H7B0.16720.54500.88610.064*
C80.01096 (18)0.30194 (19)0.87890 (17)0.0423 (4)
C90.0037 (2)0.3030 (2)0.74767 (18)0.0496 (5)
H90.07000.37050.72090.060*
C100.1075 (2)0.2025 (2)0.65635 (18)0.0514 (5)
H100.10230.20420.56840.062*
C110.21866 (18)0.0995 (2)0.69210 (17)0.0438 (4)
C120.22253 (19)0.1004 (2)0.82433 (18)0.0471 (4)
H120.29550.03240.85130.057*
C130.12109 (19)0.1994 (2)0.91630 (17)0.0453 (4)
H130.12640.19761.00420.054*
C140.3349 (2)0.0058 (2)0.5931 (2)0.0569 (5)
H14A0.30980.00630.50650.068*
H14B0.42200.01530.60660.068*
C150.22261 (19)0.2196 (2)0.51659 (19)0.0513 (5)
H15A0.23250.21520.42570.062*
H15B0.13480.14730.55740.062*
C160.1411 (2)0.3537 (2)0.69394 (19)0.0580 (5)
H16A0.20390.32150.75160.070*
H16B0.13920.44110.71210.070*
C170.0065 (2)0.2474 (2)0.72490 (18)0.0478 (5)
C180.1248 (2)0.2841 (2)0.6884 (2)0.0525 (5)
H180.11210.37400.64070.063*
C190.2608 (2)0.1888 (2)0.7222 (2)0.0528 (5)
H190.33860.21520.69710.063*
C200.28187 (19)0.0548 (2)0.7930 (2)0.0496 (5)
C210.1649 (2)0.0150 (2)0.8249 (2)0.0563 (5)
H210.17710.07600.86910.068*
C220.0292 (2)0.1125 (2)0.7901 (2)0.0532 (5)
H220.04880.08520.81190.064*
C230.4525 (2)0.1549 (2)0.9260 (2)0.0580 (5)
H23A0.55010.18270.96280.070*
H23B0.39160.13560.99540.070*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0414 (3)0.0625 (4)0.0653 (4)0.0087 (2)0.0102 (2)0.0002 (3)
S20.0542 (3)0.0573 (3)0.0473 (3)0.0124 (3)0.0042 (2)0.0047 (2)
O10.0454 (7)0.0561 (8)0.0477 (8)0.0186 (6)0.0019 (6)0.0024 (6)
O20.0366 (7)0.0482 (8)0.1132 (13)0.0165 (6)0.0125 (8)0.0137 (8)
C10.0375 (9)0.0441 (10)0.0467 (11)0.0096 (8)0.0044 (8)0.0082 (8)
C20.0331 (9)0.0408 (10)0.0523 (11)0.0089 (8)0.0015 (8)0.0058 (8)
C30.0360 (9)0.0537 (12)0.0555 (12)0.0107 (9)0.0056 (8)0.0028 (10)
C40.0446 (10)0.0589 (13)0.0508 (11)0.0030 (10)0.0051 (9)0.0147 (10)
C50.0481 (11)0.0407 (10)0.0580 (12)0.0070 (9)0.0066 (9)0.0123 (9)
C60.0377 (9)0.0347 (9)0.0479 (10)0.0069 (7)0.0035 (8)0.0002 (8)
C70.0473 (11)0.0411 (11)0.0654 (13)0.0151 (9)0.0018 (9)0.0025 (9)
C80.0378 (9)0.0475 (10)0.0440 (10)0.0213 (8)0.0043 (7)0.0045 (8)
C90.0433 (10)0.0585 (12)0.0467 (11)0.0141 (9)0.0101 (8)0.0150 (9)
C100.0504 (11)0.0681 (13)0.0388 (10)0.0217 (10)0.0059 (8)0.0161 (9)
C110.0367 (9)0.0547 (11)0.0432 (10)0.0208 (8)0.0018 (8)0.0095 (9)
C120.0398 (10)0.0536 (11)0.0502 (11)0.0164 (9)0.0087 (8)0.0152 (9)
C130.0483 (10)0.0553 (12)0.0372 (9)0.0235 (9)0.0085 (8)0.0104 (9)
C140.0425 (10)0.0708 (14)0.0557 (12)0.0215 (10)0.0033 (9)0.0069 (11)
C150.0418 (10)0.0607 (13)0.0460 (11)0.0119 (9)0.0064 (8)0.0086 (9)
C160.0497 (11)0.0672 (14)0.0489 (11)0.0055 (10)0.0019 (9)0.0189 (10)
C170.0460 (10)0.0531 (12)0.0452 (10)0.0136 (9)0.0042 (8)0.0184 (9)
C180.0567 (12)0.0465 (11)0.0566 (12)0.0191 (10)0.0088 (9)0.0133 (9)
C190.0490 (11)0.0500 (12)0.0701 (13)0.0262 (9)0.0157 (10)0.0202 (10)
C200.0368 (9)0.0454 (11)0.0723 (14)0.0160 (8)0.0088 (9)0.0223 (10)
C210.0444 (11)0.0468 (11)0.0808 (15)0.0199 (9)0.0069 (10)0.0134 (11)
C220.0398 (10)0.0599 (13)0.0672 (13)0.0229 (9)0.0094 (9)0.0197 (11)
C230.0435 (11)0.0531 (12)0.0794 (15)0.0189 (10)0.0002 (10)0.0158 (11)
Geometric parameters (Å, º) top
S1—C151.805 (2)C10—C111.387 (3)
S1—C141.810 (3)C10—H100.9300
S2—C151.786 (2)C11—C121.389 (3)
S2—C161.820 (2)C11—C141.511 (3)
O1—C81.370 (2)C12—C131.375 (3)
O1—C71.425 (2)C12—H120.9300
O2—C201.377 (2)C13—H130.9300
O2—C231.435 (3)C14—H14A0.9700
C1—C61.382 (3)C14—H14B0.9700
C1—C21.390 (2)C15—H15A0.9700
C1—H10.9300C15—H15B0.9700
C2—C31.393 (3)C16—C171.508 (3)
C2—C231.495 (3)C16—H16A0.9700
C3—C41.377 (3)C16—H16B0.9700
C3—H30.9300C17—C221.368 (3)
C4—C51.386 (3)C17—C181.394 (3)
C4—H40.9300C18—C191.382 (3)
C5—C61.381 (3)C18—H180.9300
C5—H50.9300C19—C201.381 (3)
C6—C71.509 (3)C19—H190.9300
C7—H7A0.9700C20—C211.387 (3)
C7—H7B0.9700C21—C221.389 (3)
C8—C91.384 (3)C21—H210.9300
C8—C131.387 (3)C22—H220.9300
C9—C101.389 (3)C23—H23A0.9700
C9—H90.9300C23—H23B0.9700
C15—S1—C14100.7 (1)C12—C13—H13119.8
C15—S2—C16101.7 (1)C8—C13—H13119.8
C8—O1—C7118.0 (2)C11—C14—S1115.7 (1)
C20—O2—C23118.4 (2)C11—C14—H14A108.3
C6—C1—C2122.1 (2)S1—C14—H14A108.3
C6—C1—H1118.9C11—C14—H14B108.3
C2—C1—H1118.9S1—C14—H14B108.3
C1—C2—C3118.2 (2)H14A—C14—H14B107.4
C1—C2—C23120.4 (2)S2—C15—S1111.2 (1)
C3—C2—C23121.4 (2)S2—C15—H15A109.4
C4—C3—C2120.2 (2)S1—C15—H15A109.4
C4—C3—H3119.9S2—C15—H15B109.4
C2—C3—H3119.9S1—C15—H15B109.4
C3—C4—C5120.6 (2)H15A—C15—H15B108.0
C3—C4—H4119.7C17—C16—S2114.2 (1)
C5—C4—H4119.7C17—C16—H16A108.7
C6—C5—C4120.4 (2)S2—C16—H16A108.7
C6—C5—H5119.8C17—C16—H16B108.7
C4—C5—H5119.8S2—C16—H16B108.7
C5—C6—C1118.6 (2)H16A—C16—H16B107.6
C5—C6—C7122.2 (2)C22—C17—C18117.8 (2)
C1—C6—C7119.2 (2)C22—C17—C16121.5 (2)
O1—C7—C6112.5 (2)C18—C17—C16120.8 (2)
O1—C7—H7A109.1C19—C18—C17120.9 (2)
C6—C7—H7A109.1C19—C18—H18119.5
O1—C7—H7B109.1C17—C18—H18119.5
C6—C7—H7B109.1C18—C19—C20120.4 (2)
H7A—C7—H7B107.8C18—C19—H19119.8
O1—C8—C9125.7 (2)C20—C19—H19119.8
O1—C8—C13115.1 (2)O2—C20—C19115.4 (2)
C9—C8—C13119.2 (2)O2—C20—C21125.4 (2)
C8—C9—C10119.4 (2)C19—C20—C21119.2 (2)
C8—C9—H9120.3C20—C21—C22119.3 (2)
C10—C9—H9120.3C20—C21—H21120.3
C11—C10—C9122.1 (2)C22—C21—H21120.3
C11—C10—H10118.9C17—C22—C21122.2 (2)
C9—C10—H10118.9C17—C22—H22118.9
C10—C11—C12117.2 (2)C21—C22—H22118.9
C10—C11—C14121.9 (2)O2—C23—C2113.9 (2)
C12—C11—C14120.9 (2)O2—C23—H23A108.8
C13—C12—C11121.6 (2)C2—C23—H23A108.8
C13—C12—H12119.2O2—C23—H23B108.8
C11—C12—H12119.2C2—C23—H23B108.8
C12—C13—C8120.5 (2)H23A—C23—H23B107.7
C6—C1—C2—C31.7 (3)C9—C8—C13—C120.4 (3)
C6—C1—C2—C23177.9 (2)C10—C11—C14—S1128.6 (2)
C1—C2—C3—C40.2 (3)C12—C11—C14—S154.2 (2)
C23—C2—C3—C4179.9 (2)C11—C14—S1—C1577.0 (2)
C2—C3—C4—C51.5 (3)S1—C15—S2—C1676.3 (1)
C3—C4—C5—C60.9 (3)S2—C15—S1—C14171.8 (1)
C4—C5—C6—C11.0 (3)C17—C16—S2—C1563.1 (2)
C4—C5—C6—C7177.8 (2)S2—C16—C17—C22101.7 (2)
C2—C1—C6—C52.3 (3)S2—C16—C17—C1878.8 (2)
C2—C1—C6—C7176.5 (2)C22—C17—C18—C192.8 (3)
C6—C7—O1—C872.7 (2)C16—C17—C18—C19176.8 (2)
C5—C6—C7—O1143.5 (2)C17—C18—C19—C200.1 (3)
C1—C6—C7—O135.3 (2)C23—O2—C20—C19164.6 (2)
C7—O1—C8—C92.7 (3)C23—O2—C20—C2115.2 (3)
C7—O1—C8—C13178.0 (2)C18—C19—C20—O2177.0 (2)
O1—C8—C9—C10178.6 (2)C18—C19—C20—C212.8 (3)
C13—C8—C9—C100.6 (3)O2—C20—C21—C22176.9 (2)
C8—C9—C10—C110.4 (3)C19—C20—C21—C222.9 (3)
C9—C10—C11—C120.0 (3)C18—C17—C22—C212.7 (3)
C9—C10—C11—C14177.2 (2)C16—C17—C22—C21176.9 (2)
C10—C11—C12—C130.3 (3)C20—C21—C22—C170.1 (3)
C14—C11—C12—C13177.0 (2)C2—C23—O2—C2080.5 (2)
C11—C12—C13—C80.1 (3)C1—C2—C23—O2120.9 (2)
O1—C8—C13—C12179.0 (2)C3—C2—C23—O258.7 (2)
 

Subscribe to Acta Crystallographica Section E: Crystallographic Communications

The full text of this article is available to subscribers to the journal.

If you have already registered and are using a computer listed in your registration details, please email support@iucr.org for assistance.

Buy online

You may purchase this article in PDF and/or HTML formats. For purchasers in the European Community who do not have a VAT number, VAT will be added at the local rate. Payments to the IUCr are handled by WorldPay, who will accept payment by credit card in several currencies. To purchase the article, please complete the form below (fields marked * are required), and then click on `Continue'.
E-mail address* 
Repeat e-mail address* 
(for error checking) 

Format*   PDF (US $40)
   HTML (US $40)
   PDF+HTML (US $50)
In order for VAT to be shown for your country javascript needs to be enabled.

VAT number 
(non-UK EC countries only) 
Country* 
 

Terms and conditions of use
Contact us

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