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The title compound, C16H18S2 (or L6), crystallizes with two half-mol­ecules in the asymmetric unit and each independent mol­ecule lies about a crystallographic center of symmetry. The aliphatic segment of this ligand is in an all-trans conformation.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805020465/lh6461sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805020465/lh6461Isup2.hkl
Contains datablock I

CCDC reference: 282534

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C) = 0.005 Å
  • R factor = 0.036
  • wR factor = 0.068
  • Data-to-parameter ratio = 17.0

checkCIF/PLATON results

No syntax errors found



Alert level C GOODF01_ALERT_2_C The least squares goodness of fit parameter lies outside the range 0.80 <> 2.00 Goodness of fit given = 0.663 PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low .... 41 Perc. PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 5
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 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 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CAD-4 Software; data reduction: local Program; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: UdMX (local program).

1,6-Bis(phenylsulfanyl)hexane top
Crystal data top
C18H22S2Z = 2
Mr = 302.48F(000) = 324
Triclinic, P1Dx = 1.233 Mg m3
Hall symbol: -P 1Cu Kα radiation, λ = 1.54178 Å
a = 5.627 (2) ÅCell parameters from 25 reflections
b = 7.862 (3) Åθ = 20.0–25.0°
c = 18.486 (6) ŵ = 2.84 mm1
α = 94.55 (3)°T = 298 K
β = 91.36 (3)°Platelet, colorless
γ = 90.46 (3)°0.23 × 0.15 × 0.02 mm
V = 815.0 (5) Å3
Data collection top
Enraf–Nonius CAD-4
diffractometer
1270 reflections with I > 2σ(I)
Radiation source: X-ray sealed tubeRint = 0.059
Graphite monochromatorθmax = 69.8°, θmin = 2.4°
ω scansh = 66
Absorption correction: gaussian
from crystal shape
k = 99
Tmin = 0.560, Tmax = 0.940l = 2222
25176 measured reflections5 standard reflections every 60 min
3086 independent reflections intensity decay: 0.03%
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)] = 0.036Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.068H-atom parameters constrained
S = 0.66 w = 1/[σ2(Fo2) + (0.0003P)2]
where P = (Fo2 + 2Fc2)/3
3086 reflections(Δ/σ)max < 0.001
181 parametersΔρmax = 0.16 e Å3
0 restraintsΔρmin = 0.25 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
S10.53505 (18)0.43816 (12)0.19100 (5)0.0541 (3)
S20.02359 (18)0.10379 (12)0.81264 (5)0.0550 (3)
C110.5038 (6)0.3818 (4)0.28080 (18)0.0380 (9)
C120.6791 (6)0.4380 (4)0.33127 (18)0.0468 (9)
H120.80620.50260.31680.056*
C130.6676 (7)0.3993 (4)0.40260 (19)0.0561 (10)
H130.78670.43740.43590.067*
C140.4797 (7)0.3044 (4)0.4245 (2)0.0530 (11)
H140.47120.27880.47270.064*
C150.3050 (6)0.2477 (4)0.37524 (18)0.0499 (10)
H150.17830.18340.39020.060*
C160.3155 (6)0.2852 (4)0.30332 (17)0.0448 (9)
H160.19660.24580.27020.054*
C170.2411 (6)0.4137 (4)0.15052 (17)0.0477 (10)
H17A0.19410.29430.14660.057*
H17B0.12800.47700.18070.057*
C180.2419 (7)0.4804 (4)0.07560 (18)0.0510 (10)
H18A0.29290.59900.08010.061*
H18B0.35600.41650.04610.061*
C190.0008 (7)0.4667 (4)0.03759 (17)0.0490 (10)
H19A0.11320.53040.06720.059*
H19B0.05000.34800.03310.059*
C210.0013 (6)0.1337 (4)0.71941 (18)0.0381 (9)
C220.1808 (6)0.2228 (4)0.68801 (18)0.0438 (9)
H220.30410.26620.71630.053*
C230.1796 (6)0.2472 (4)0.61519 (18)0.0497 (10)
H230.30310.30640.59460.060*
C240.0026 (7)0.1850 (4)0.5723 (2)0.0531 (11)
H240.00280.20200.52310.064*
C250.1846 (6)0.0970 (4)0.60347 (17)0.0489 (9)
H250.30800.05460.57490.059*
C260.1860 (6)0.0713 (4)0.67650 (17)0.0433 (9)
H260.31000.01240.69690.052*
C270.2719 (6)0.0575 (4)0.84401 (18)0.0494 (10)
H27A0.32510.04960.82040.059*
H27B0.38140.14710.83280.059*
C280.2646 (7)0.0459 (4)0.92555 (19)0.0525 (11)
H28A0.20860.15330.94810.063*
H28B0.15130.04230.93560.063*
C290.5031 (7)0.0063 (5)0.95945 (17)0.0523 (10)
H29A0.61610.09480.94950.063*
H29B0.55940.10080.93670.063*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0490 (7)0.0737 (7)0.0412 (6)0.0039 (5)0.0037 (5)0.0153 (5)
S20.0480 (7)0.0815 (8)0.0366 (6)0.0043 (5)0.0020 (5)0.0123 (5)
C110.042 (2)0.035 (2)0.037 (2)0.0048 (16)0.0012 (18)0.0044 (15)
C120.038 (2)0.049 (2)0.054 (2)0.0042 (17)0.0024 (18)0.0079 (18)
C130.061 (3)0.055 (3)0.051 (2)0.002 (2)0.021 (2)0.0068 (19)
C140.068 (3)0.055 (3)0.037 (2)0.003 (2)0.004 (2)0.0099 (18)
C150.052 (3)0.058 (2)0.042 (2)0.0073 (19)0.0012 (18)0.0115 (18)
C160.045 (2)0.051 (2)0.0380 (19)0.0079 (18)0.0079 (17)0.0060 (17)
C170.053 (3)0.055 (2)0.036 (2)0.0010 (19)0.0032 (19)0.0070 (18)
C180.065 (3)0.055 (2)0.034 (2)0.000 (2)0.003 (2)0.0117 (18)
C190.058 (3)0.059 (2)0.032 (2)0.0005 (19)0.0030 (19)0.0102 (17)
C210.044 (2)0.036 (2)0.034 (2)0.0076 (16)0.0054 (18)0.0050 (15)
C220.037 (2)0.048 (2)0.045 (2)0.0043 (17)0.0024 (17)0.0006 (18)
C230.053 (3)0.053 (2)0.044 (2)0.0049 (19)0.0142 (18)0.0104 (18)
C240.070 (3)0.053 (3)0.037 (2)0.011 (2)0.007 (2)0.0083 (18)
C250.052 (2)0.057 (2)0.038 (2)0.0031 (19)0.0072 (18)0.0040 (18)
C260.043 (2)0.046 (2)0.042 (2)0.0067 (17)0.0025 (17)0.0078 (17)
C270.058 (3)0.057 (2)0.034 (2)0.0063 (19)0.0062 (19)0.0101 (18)
C280.060 (3)0.061 (3)0.037 (2)0.003 (2)0.007 (2)0.0119 (18)
C290.061 (3)0.063 (2)0.034 (2)0.0085 (19)0.008 (2)0.0101 (19)
Geometric parameters (Å, º) top
S1—C111.764 (3)C19—H19a0.97
S1—C171.802 (3)C19—H19b0.97
S2—C211.766 (3)C21—C261.391 (4)
S2—C271.798 (3)C21—C221.388 (4)
C11—C161.390 (4)C22—C231.375 (4)
C11—C121.387 (4)C22—H220.93
C12—C131.379 (4)C23—C241.380 (4)
C12—H120.93C23—H230.93
C13—C141.377 (4)C24—C251.381 (4)
C13—H130.93C24—H240.93
C14—C151.372 (4)C25—C261.381 (4)
C14—H140.93C25—H250.93
C15—C161.387 (4)C26—H260.93
C15—H150.93C27—C281.519 (4)
C16—H160.93C27—H27a0.97
C17—C181.519 (4)C27—H27b0.97
C17—H17a0.97C28—C291.513 (4)
C17—H17b0.97C28—H28a0.97
C18—C191.512 (4)C28—H28b0.97
C18—H18a0.97C29—C29ii1.512 (6)
C18—H18b0.97C29—H29a0.97
C19—C19i1.524 (6)C29—H29b0.97
C11—S1—C17104.78 (17)H19A—C19—H19B107.7
C21—S2—C27105.51 (17)C26—C21—C22119.2 (3)
C16—C11—C12118.8 (3)C26—C21—S2124.4 (3)
C16—C11—S1123.9 (3)C22—C21—S2116.4 (3)
C12—C11—S1117.3 (3)C23—C22—C21120.3 (3)
C11—C12—C13120.9 (3)C23—C22—H22119.9
C11—C12—H12119.6C21—C22—H22119.9
C13—C12—H12119.6C24—C23—C22120.8 (3)
C14—C13—C12120.0 (3)C24—C23—H23119.6
C14—C13—H13120C22—C23—H23119.6
C12—C13—H13120C23—C24—C25119.0 (3)
C13—C14—C15119.9 (3)C23—C24—H24120.5
C13—C14—H14120.1C25—C24—H24120.5
C15—C14—H14120.1C24—C25—C26120.9 (3)
C14—C15—C16120.6 (3)C24—C25—H25119.6
C14—C15—H15119.7C26—C25—H25119.6
C16—C15—H15119.7C21—C26—C25119.8 (3)
C11—C16—C15119.9 (3)C21—C26—H26120.1
C11—C16—H16120C25—C26—H26120.1
C15—C16—H16120C28—C27—S2107.7 (3)
C18—C17—S1109.0 (3)C28—C27—H27A110.2
C18—C17—H17A109.9S2—C27—H27A110.2
S1—C17—H17A109.9C28—C27—H27B110.2
C18—C17—H17B109.9S2—C27—H27B110.2
S1—C17—H17B109.9H27A—C27—H27B108.5
H17A—C17—H17B108.3C29—C28—C27113.4 (3)
C19—C18—C17112.8 (3)C29—C28—H28A108.9
C19—C18—H18A109C27—C28—H28A108.9
C17—C18—H18A109C29—C28—H28B108.9
C19—C18—H18B109C27—C28—H28B108.9
C17—C18—H18B109H28A—C28—H28B107.7
H18A—C18—H18B107.8C28—C29—C29ii113.7 (4)
C18—C19—C19i113.3 (4)C28—C29—H29A108.8
C18—C19—H19A108.9C29ii—C29—H29A108.8
C19i—C19—H19A108.9C28—C29—H29B108.8
C18—C19—H19B108.9C29ii—C29—H29B108.8
C19i—C19—H19B108.9H29A—C29—H29B107.7
C17—S1—C11—C1619.8 (3)C27—S2—C21—C2621.4 (3)
C17—S1—C11—C12160.3 (3)C27—S2—C21—C22160.0 (2)
C16—C11—C12—C130.1 (5)C26—C21—C22—C230.7 (5)
S1—C11—C12—C13180.0 (3)S2—C21—C22—C23177.9 (2)
C11—C12—C13—C140.3 (5)C21—C22—C23—C240.5 (5)
C12—C13—C14—C150.4 (6)C22—C23—C24—C250.1 (5)
C13—C14—C15—C160.1 (6)C23—C24—C25—C260.1 (5)
C12—C11—C16—C150.4 (5)C22—C21—C26—C250.7 (5)
S1—C11—C16—C15179.7 (3)S2—C21—C26—C25177.9 (2)
C14—C15—C16—C110.3 (5)C24—C25—C26—C210.3 (5)
C11—S1—C17—C18173.0 (2)C21—S2—C27—C28175.1 (2)
S1—C17—C18—C19179.4 (2)S2—C27—C28—C29179.7 (2)
C17—C18—C19—C19i179.9 (4)C27—C28—C29—C29ii179.7 (4)
Symmetry codes: (i) x, y+1, z; (ii) x+1, y, z+2.
 

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