Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536810052165/jh2245sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536810052165/jh2245Isup2.hkl |
CCDC reference: 782396
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C) = 0.008 Å
- R factor = 0.057
- wR factor = 0.183
- Data-to-parameter ratio = 17.7
checkCIF/PLATON results
No syntax errors found
Alert level C SHFSU01_ALERT_2_C The absolute value of parameter shift to su ratio > 0.05 Absolute value of the parameter shift to su ratio given 0.061 Additional refinement cycles may be required. PLAT080_ALERT_2_C Maximum Shift/Error ............................ 0.06 PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density .... 2.95 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for S1 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C20 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C23 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for S2 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C6 PLAT331_ALERT_2_C Small Average Phenyl C-C Dist. C1 -C6 1.37 Ang. PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang .. 8 PLAT910_ALERT_3_C Missing # of FCF Reflections Below Th(Min) ..... 1 PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L= 0.600 3 PLAT915_ALERT_3_C Low Friedel Pair Coverage ...................... 71.47 Perc. PLAT912_ALERT_4_C Missing # of FCF Reflections Above STh/L= 0.600 129
Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 28.30 From the CIF: _reflns_number_total 5111 Count of symmetry unique reflns 3196 Completeness (_total/calc) 159.92% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 1915 Fraction of Friedel pairs measured 0.599 Are heavy atom types Z>Si present yes PLAT908_ALERT_2_G Max. Perc. Data with I .gt. 2*s(I) per Res.Shell 70.43 Perc. PLAT850_ALERT_4_G Check Flack Parameter Exact Value 0.00 and su .. 0.12
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 14 ALERT level C = Check and explain 3 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 10 ALERT type 2 Indicator that the structure model may be wrong or deficient 4 ALERT type 3 Indicator that the structure quality may be low 3 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
The title compound was prepared refering to the literature method (Shriner et al., 1930) with little modification. Sodium sulfide(99%, 0.312 g, 0.0040 mol) and benzylchloride (1.000 g, 0.0079 mol) were dissolved in anhydrous ethanol (50 ml) at 70°C, and then was stirred over 1 h. The solution was extracted with CH2Cl2 after addition 400 ml of water. Dibenzyl sulfide(0.736 g, 0.0034 mol) was obtained after evaporation of CH2Cl2. Yield: 86%. Hydrogen peroxide (30%, 0.0028 mol) was added dropwise to a solution of dibenzyl sulfide (0.600 g, 0.0028 mol) in acetic acid (60 ml) on ice bath with a vigorously stir for 1 h. 500 ml of water was added. The solution was extracted with CH2Cl2, and the product of dibenzyl sulfoxide(0.552 g, 0.0024 mol) was obtained after evaporation of CH2Cl2. Yield: 86%. It was characterized by recording its infrared and NMR spectra. White single crystals of the title compound were obtained by slow evaporation of its mixed solution including n-hexane and dichloromethane.)
(All H atoms were placed in calculated positions and subsequently constrained to ride on their parent atoms, with C–H distances of 0.93 Å (C-aromatic) and 0.97 Å (C-methyl). The Uiso(H) values were set at 1.2 Ueq(C aromatic) and 1.5 Ueq(C methylene).)
Sulfoxides have been widely used in the separation of palladium from other platinum-group metals by solvent extraction (Xu et al., 2006).A similar disulfoxide ligand 1,6-bis(benzylsulfinyl)hexane and its Copper(II) and Cadmium(II) dimeric complexes were obtained (Li et al.,2003). Crystals of dibenzyl sulfoxide show two independent molecules in the unit. There are asymmetry S—C bonds in a same molecule. The long axe of the crystals is directed along the b axis.
For related structures, see: Li et al. (2003); Iitaka et al. (1986)
For related literature, see: Shriner et al. (1930); Xu et al. (2006).
Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).
Fig. 1. Molecule structure of with displacement ellipsoids drawn at the 50% probability level. |
C14H14OS | F(000) = 3904 |
Mr = 230.32 | Dx = 1.258 Mg m−3 |
Orthorhombic, Fdd2 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: F 2 -2d | Cell parameters from 2370 reflections |
a = 17.882 (5) Å | θ = 2.3–23.7° |
b = 53.150 (14) Å | µ = 0.24 mm−1 |
c = 10.233 (3) Å | T = 298 K |
V = 9726 (5) Å3 | Block, white |
Z = 32 | 0.36 × 0.28 × 0.15 mm |
Bruker APEXII CCD area-detector diffractometer | 2563 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.042 |
Graphite monochromator | θmax = 28.3°, θmin = 2.3° |
phi and ω scans | h = −23→22 |
14310 measured reflections | k = −56→69 |
5111 independent reflections | l = −11→13 |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.057 | H-atom parameters constrained |
wR(F2) = 0.183 | w = 1/[σ2(Fo2) + (0.0957P)2] where P = (Fo2 + 2Fc2)/3 |
S = 0.97 | (Δ/σ)max = 0.061 |
5111 reflections | Δρmax = 0.56 e Å−3 |
289 parameters | Δρmin = −0.19 e Å−3 |
1 restraint | Absolute structure: Flack (1983), 1074 Friedel pairs |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.00 (12) |
C14H14OS | V = 9726 (5) Å3 |
Mr = 230.32 | Z = 32 |
Orthorhombic, Fdd2 | Mo Kα radiation |
a = 17.882 (5) Å | µ = 0.24 mm−1 |
b = 53.150 (14) Å | T = 298 K |
c = 10.233 (3) Å | 0.36 × 0.28 × 0.15 mm |
Bruker APEXII CCD area-detector diffractometer | 2563 reflections with I > 2σ(I) |
14310 measured reflections | Rint = 0.042 |
5111 independent reflections |
R[F2 > 2σ(F2)] = 0.057 | H-atom parameters constrained |
wR(F2) = 0.183 | Δρmax = 0.56 e Å−3 |
S = 0.97 | Δρmin = −0.19 e Å−3 |
5111 reflections | Absolute structure: Flack (1983), 1074 Friedel pairs |
289 parameters | Absolute structure parameter: 0.00 (12) |
1 restraint |
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. |
x | y | z | Uiso*/Ueq | ||
S1 | 0.40616 (7) | 0.12486 (3) | 0.42542 (10) | 0.0541 (3) | |
C6 | 0.1374 (2) | 0.07435 (9) | 0.7186 (5) | 0.0511 (13) | |
C9 | 0.1385 (3) | 0.17549 (9) | 0.7183 (5) | 0.0547 (13) | |
C7 | 0.1315 (3) | 0.10024 (9) | 0.7775 (5) | 0.0657 (13) | |
H7A | 0.1713 | 0.1024 | 0.8410 | 0.079* | |
H7B | 0.0842 | 0.1017 | 0.8233 | 0.079* | |
C8 | 0.1322 (3) | 0.14959 (9) | 0.7780 (5) | 0.0637 (13) | |
H8A | 0.0850 | 0.1483 | 0.8241 | 0.076* | |
H8B | 0.1720 | 0.1474 | 0.8412 | 0.076* | |
C4 | 0.0819 (3) | 0.03513 (11) | 0.6580 (6) | 0.0878 (18) | |
H4 | 0.0400 | 0.0248 | 0.6511 | 0.105* | |
C13 | 0.2163 (3) | 0.20854 (11) | 0.6307 (6) | 0.0814 (16) | |
H13 | 0.2630 | 0.2144 | 0.6045 | 0.098* | |
C1 | 0.2051 (3) | 0.06488 (10) | 0.6809 (6) | 0.0693 (13) | |
H1 | 0.2475 | 0.0749 | 0.6894 | 0.083* | |
C2 | 0.2122 (3) | 0.04126 (10) | 0.6312 (6) | 0.0796 (16) | |
H2 | 0.2590 | 0.0355 | 0.6050 | 0.096* | |
C5 | 0.0754 (3) | 0.05917 (11) | 0.7057 (6) | 0.0747 (15) | |
H5 | 0.0286 | 0.0653 | 0.7297 | 0.090* | |
C3 | 0.1526 (4) | 0.02621 (10) | 0.6196 (6) | 0.0782 (17) | |
H3 | 0.1578 | 0.0100 | 0.5865 | 0.094* | |
C11 | 0.0846 (3) | 0.21459 (11) | 0.6523 (6) | 0.0790 (17) | |
H11 | 0.0425 | 0.2247 | 0.6414 | 0.095* | |
C14 | 0.2086 (3) | 0.18479 (9) | 0.6809 (6) | 0.0697 (14) | |
H14 | 0.2507 | 0.1747 | 0.6903 | 0.084* | |
C12 | 0.1542 (3) | 0.22363 (10) | 0.6195 (6) | 0.0774 (17) | |
H12 | 0.1593 | 0.2401 | 0.5896 | 0.093* | |
C10 | 0.0773 (3) | 0.19068 (10) | 0.7010 (5) | 0.0707 (15) | |
H10 | 0.0301 | 0.1847 | 0.7227 | 0.085* | |
C17 | 0.4166 (3) | 0.02607 (10) | 0.3893 (7) | 0.0738 (16) | |
H17 | 0.4294 | 0.0096 | 0.3678 | 0.089* | |
C26 | 0.4207 (3) | 0.22365 (10) | 0.3836 (7) | 0.0742 (16) | |
H26 | 0.4354 | 0.2399 | 0.3609 | 0.089* | |
C15 | 0.4119 (3) | 0.05920 (10) | 0.5446 (6) | 0.0726 (15) | |
H15 | 0.4225 | 0.0653 | 0.6277 | 0.087* | |
C22 | 0.3498 (3) | 0.14955 (10) | 0.4925 (6) | 0.0674 (14) | |
H22A | 0.2987 | 0.1474 | 0.4630 | 0.081* | |
H22B | 0.3501 | 0.1482 | 0.5870 | 0.081* | |
C24 | 0.3599 (3) | 0.18525 (10) | 0.3314 (6) | 0.0695 (15) | |
H24 | 0.3334 | 0.1755 | 0.2718 | 0.083* | |
C28 | 0.4160 (3) | 0.19012 (10) | 0.5414 (6) | 0.0737 (15) | |
H28 | 0.4283 | 0.1839 | 0.6236 | 0.088* | |
C19 | 0.3607 (3) | 0.06475 (10) | 0.3319 (6) | 0.0697 (14) | |
H19 | 0.3366 | 0.0749 | 0.2710 | 0.084* | |
C20 | 0.3754 (3) | 0.07420 (9) | 0.4574 (5) | 0.0525 (13) | |
C16 | 0.4335 (3) | 0.03512 (10) | 0.5121 (6) | 0.0823 (17) | |
H16 | 0.4589 | 0.0251 | 0.5720 | 0.099* | |
C27 | 0.4374 (3) | 0.21400 (10) | 0.5059 (7) | 0.0844 (18) | |
H27 | 0.4636 | 0.2239 | 0.5652 | 0.101* | |
C21 | 0.3494 (3) | 0.10017 (9) | 0.4944 (6) | 0.0655 (14) | |
H21A | 0.3498 | 0.1017 | 0.5888 | 0.079* | |
H21B | 0.2982 | 0.1023 | 0.4652 | 0.079* | |
C23 | 0.3763 (3) | 0.17547 (9) | 0.4545 (5) | 0.0537 (13) | |
C25 | 0.3822 (3) | 0.20898 (11) | 0.2968 (6) | 0.0818 (16) | |
H25 | 0.3711 | 0.2151 | 0.2140 | 0.098* | |
C18 | 0.3813 (3) | 0.04094 (12) | 0.2979 (6) | 0.0823 (16) | |
H18 | 0.3716 | 0.0348 | 0.2144 | 0.099* | |
O1 | 0.47890 (18) | 0.12488 (7) | 0.4984 (4) | 0.0831 (11) | |
O2 | 0.0644 (2) | 0.12505 (7) | 0.5840 (4) | 0.0850 (11) | |
S2 | 0.13762 (7) | 0.12488 (3) | 0.65757 (9) | 0.0548 (3) |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0557 (6) | 0.0490 (6) | 0.0575 (8) | 0.0010 (6) | 0.0076 (5) | 0.0000 (7) |
C6 | 0.057 (3) | 0.044 (3) | 0.053 (3) | −0.003 (2) | −0.002 (2) | 0.007 (2) |
C9 | 0.064 (3) | 0.048 (3) | 0.052 (3) | 0.005 (2) | −0.010 (2) | −0.010 (3) |
C7 | 0.080 (3) | 0.064 (3) | 0.053 (3) | −0.005 (3) | −0.002 (3) | 0.006 (3) |
C8 | 0.083 (3) | 0.061 (3) | 0.047 (3) | 0.000 (2) | −0.004 (3) | −0.006 (2) |
C4 | 0.100 (4) | 0.077 (4) | 0.086 (4) | −0.037 (3) | −0.024 (4) | 0.003 (4) |
C13 | 0.082 (4) | 0.076 (4) | 0.087 (4) | −0.009 (3) | 0.000 (3) | −0.002 (3) |
C1 | 0.064 (3) | 0.066 (3) | 0.078 (4) | −0.005 (2) | −0.002 (3) | 0.009 (3) |
C2 | 0.088 (4) | 0.066 (4) | 0.085 (4) | 0.009 (3) | 0.007 (3) | 0.007 (3) |
C5 | 0.063 (3) | 0.079 (4) | 0.082 (4) | −0.002 (3) | −0.017 (3) | 0.006 (3) |
C3 | 0.121 (5) | 0.048 (4) | 0.066 (4) | −0.007 (3) | −0.004 (4) | −0.003 (3) |
C11 | 0.079 (4) | 0.070 (4) | 0.088 (4) | 0.022 (3) | −0.019 (4) | −0.015 (3) |
C14 | 0.061 (3) | 0.068 (3) | 0.080 (4) | 0.009 (2) | −0.007 (3) | −0.009 (3) |
C12 | 0.114 (5) | 0.050 (4) | 0.068 (4) | 0.005 (3) | −0.006 (3) | −0.007 (3) |
C10 | 0.057 (3) | 0.077 (4) | 0.079 (4) | 0.004 (2) | −0.008 (3) | −0.011 (3) |
C17 | 0.073 (3) | 0.054 (4) | 0.094 (5) | 0.002 (3) | 0.010 (3) | 0.001 (3) |
C26 | 0.074 (3) | 0.051 (4) | 0.098 (5) | 0.002 (3) | 0.009 (3) | −0.005 (3) |
C15 | 0.072 (3) | 0.080 (4) | 0.065 (3) | −0.001 (3) | −0.014 (3) | 0.008 (3) |
C22 | 0.061 (3) | 0.066 (4) | 0.074 (4) | 0.005 (2) | 0.014 (3) | −0.008 (3) |
C24 | 0.072 (3) | 0.059 (3) | 0.077 (4) | 0.004 (2) | −0.007 (3) | −0.011 (3) |
C28 | 0.074 (3) | 0.069 (4) | 0.078 (4) | 0.011 (3) | −0.014 (3) | −0.014 (3) |
C19 | 0.075 (3) | 0.064 (3) | 0.070 (4) | −0.002 (3) | −0.013 (3) | 0.009 (3) |
C20 | 0.051 (3) | 0.048 (3) | 0.058 (3) | −0.005 (2) | 0.004 (2) | 0.006 (3) |
C16 | 0.081 (4) | 0.072 (4) | 0.094 (5) | 0.008 (3) | −0.010 (4) | 0.021 (3) |
C27 | 0.074 (4) | 0.069 (4) | 0.110 (5) | −0.001 (3) | −0.016 (4) | −0.033 (3) |
C21 | 0.063 (3) | 0.063 (3) | 0.071 (4) | −0.002 (2) | 0.013 (3) | 0.001 (3) |
C23 | 0.052 (3) | 0.046 (3) | 0.063 (3) | 0.007 (2) | 0.006 (2) | −0.007 (3) |
C25 | 0.091 (4) | 0.074 (4) | 0.080 (4) | 0.015 (3) | 0.002 (3) | 0.005 (3) |
C18 | 0.096 (4) | 0.077 (4) | 0.073 (4) | −0.008 (3) | −0.003 (3) | −0.006 (3) |
O1 | 0.0486 (17) | 0.083 (2) | 0.117 (3) | 0.0017 (15) | −0.011 (2) | −0.004 (3) |
O2 | 0.088 (3) | 0.099 (3) | 0.067 (2) | 0.001 (2) | −0.034 (2) | 0.003 (2) |
S2 | 0.0703 (8) | 0.0508 (6) | 0.0434 (6) | 0.0005 (6) | 0.0020 (6) | −0.0014 (7) |
S1—O1 | 1.500 (3) | C10—H10 | 0.9300 |
S1—C22 | 1.791 (5) | C17—C18 | 1.378 (8) |
S1—C21 | 1.804 (5) | C17—C16 | 1.379 (8) |
C6—C1 | 1.367 (6) | C17—H17 | 0.9300 |
C6—C5 | 1.378 (6) | C26—C25 | 1.368 (8) |
C6—C7 | 1.506 (6) | C26—C27 | 1.385 (8) |
C9—C10 | 1.371 (6) | C26—H26 | 0.9300 |
C9—C14 | 1.401 (6) | C15—C20 | 1.363 (7) |
C9—C8 | 1.510 (6) | C15—C16 | 1.377 (7) |
C7—S2 | 1.798 (5) | C15—H15 | 0.9300 |
C7—H7A | 0.9700 | C22—C23 | 1.508 (7) |
C7—H7B | 0.9700 | C22—H22A | 0.9700 |
C8—S2 | 1.804 (5) | C22—H22B | 0.9700 |
C8—H8A | 0.9700 | C24—C25 | 1.369 (7) |
C8—H8B | 0.9700 | C24—C23 | 1.395 (7) |
C4—C5 | 1.373 (8) | C24—H24 | 0.9300 |
C4—C3 | 1.405 (8) | C28—C27 | 1.374 (8) |
C4—H4 | 0.9300 | C28—C23 | 1.379 (7) |
C13—C14 | 1.370 (7) | C28—H28 | 0.9300 |
C13—C12 | 1.375 (7) | C19—C18 | 1.363 (7) |
C13—H13 | 0.9300 | C19—C20 | 1.404 (7) |
C1—C2 | 1.360 (7) | C19—H19 | 0.9300 |
C1—H1 | 0.9300 | C20—C21 | 1.505 (6) |
C2—C3 | 1.338 (7) | C16—H16 | 0.9300 |
C2—H2 | 0.9300 | C27—H27 | 0.9300 |
C5—H5 | 0.9300 | C21—H21A | 0.9700 |
C3—H3 | 0.9300 | C21—H21B | 0.9700 |
C11—C10 | 1.371 (8) | C25—H25 | 0.9300 |
C11—C12 | 1.376 (8) | C18—H18 | 0.9300 |
C11—H11 | 0.9300 | O2—S2 | 1.511 (3) |
C14—H14 | 0.9300 | S2—C7 | 1.798 (5) |
C12—H12 | 0.9300 | S2—C8 | 1.804 (5) |
O1—S1—C22 | 107.2 (2) | C18—C17—C16 | 121.3 (6) |
O1—S1—C21 | 107.1 (2) | C18—C17—H17 | 119.4 |
C22—S1—C21 | 93.8 (2) | C16—C17—H17 | 119.4 |
C1—C6—C5 | 118.1 (5) | C25—C26—C27 | 119.0 (5) |
C1—C6—C7 | 120.8 (5) | C25—C26—H26 | 120.5 |
C5—C6—C7 | 121.1 (5) | C27—C26—H26 | 120.5 |
C10—C9—C14 | 118.1 (5) | C20—C15—C16 | 121.3 (6) |
C10—C9—C8 | 122.0 (5) | C20—C15—H15 | 119.3 |
C14—C9—C8 | 119.9 (4) | C16—C15—H15 | 119.3 |
C6—C7—S2 | 112.8 (4) | C23—C22—S1 | 113.2 (3) |
C6—C7—H7A | 109.0 | C23—C22—H22A | 108.9 |
S2—C7—H7A | 109.0 | S1—C22—H22A | 108.9 |
C6—C7—H7B | 109.0 | C23—C22—H22B | 108.9 |
S2—C7—H7B | 109.0 | S1—C22—H22B | 108.9 |
H7A—C7—H7B | 107.8 | H22A—C22—H22B | 107.7 |
C9—C8—S2 | 112.6 (4) | C25—C24—C23 | 121.0 (6) |
C9—C8—H8A | 109.1 | C25—C24—H24 | 119.5 |
S2—C8—H8A | 109.1 | C23—C24—H24 | 119.5 |
C9—C8—H8B | 109.1 | C27—C28—C23 | 119.6 (6) |
S2—C8—H8B | 109.1 | C27—C28—H28 | 120.2 |
H8A—C8—H8B | 107.8 | C23—C28—H28 | 120.2 |
C5—C4—C3 | 119.4 (5) | C18—C19—C20 | 121.0 (5) |
C5—C4—H4 | 120.3 | C18—C19—H19 | 119.5 |
C3—C4—H4 | 120.3 | C20—C19—H19 | 119.5 |
C14—C13—C12 | 119.2 (5) | C15—C20—C19 | 118.6 (5) |
C14—C13—H13 | 120.4 | C15—C20—C21 | 121.3 (5) |
C12—C13—H13 | 120.4 | C19—C20—C21 | 120.0 (5) |
C2—C1—C6 | 121.9 (5) | C15—C16—C17 | 118.9 (5) |
C2—C1—H1 | 119.1 | C15—C16—H16 | 120.6 |
C6—C1—H1 | 119.1 | C17—C16—H16 | 120.6 |
C3—C2—C1 | 120.7 (5) | C28—C27—C26 | 121.4 (5) |
C3—C2—H2 | 119.7 | C28—C27—H27 | 119.3 |
C1—C2—H2 | 119.7 | C26—C27—H27 | 119.3 |
C4—C5—C6 | 120.7 (5) | C20—C21—S1 | 113.2 (3) |
C4—C5—H5 | 119.7 | C20—C21—H21A | 108.9 |
C6—C5—H5 | 119.7 | S1—C21—H21A | 108.9 |
C2—C3—C4 | 119.3 (5) | C20—C21—H21B | 108.9 |
C2—C3—H3 | 120.3 | S1—C21—H21B | 108.9 |
C4—C3—H3 | 120.3 | H21A—C21—H21B | 107.7 |
C10—C11—C12 | 119.8 (5) | C28—C23—C24 | 118.7 (5) |
C10—C11—H11 | 120.1 | C28—C23—C22 | 120.8 (5) |
C12—C11—H11 | 120.1 | C24—C23—C22 | 120.5 (5) |
C13—C14—C9 | 121.1 (5) | C26—C25—C24 | 120.2 (6) |
C13—C14—H14 | 119.4 | C26—C25—H25 | 119.9 |
C9—C14—H14 | 119.4 | C24—C25—H25 | 119.9 |
C13—C12—C11 | 120.5 (6) | C19—C18—C17 | 118.9 (6) |
C13—C12—H12 | 119.8 | C19—C18—H18 | 120.6 |
C11—C12—H12 | 119.8 | C17—C18—H18 | 120.6 |
C11—C10—C9 | 121.1 (5) | O2—S2—C7 | 107.0 (2) |
C11—C10—H10 | 119.4 | O2—S2—C8 | 106.8 (2) |
C9—C10—H10 | 119.4 | C7—S2—C8 | 93.5 (2) |
C1—C6—C7—S2 | 77.1 (6) | C18—C19—C20—C15 | 1.0 (8) |
C5—C6—C7—S2 | −105.4 (5) | C18—C19—C20—C21 | −177.4 (5) |
C10—C9—C8—S2 | 103.3 (5) | C20—C15—C16—C17 | −0.9 (8) |
C14—C9—C8—S2 | −77.8 (6) | C18—C17—C16—C15 | 2.3 (9) |
C5—C6—C1—C2 | 0.4 (8) | C23—C28—C27—C26 | −0.8 (8) |
C7—C6—C1—C2 | 177.9 (5) | C25—C26—C27—C28 | −0.1 (9) |
C6—C1—C2—C3 | −1.2 (9) | C15—C20—C21—S1 | 105.3 (5) |
C3—C4—C5—C6 | −1.2 (9) | C19—C20—C21—S1 | −76.3 (6) |
C1—C6—C5—C4 | 0.8 (8) | O1—S1—C21—C20 | −72.8 (5) |
C7—C6—C5—C4 | −176.7 (5) | C22—S1—C21—C20 | 177.8 (4) |
C1—C2—C3—C4 | 0.7 (9) | C27—C28—C23—C24 | 1.0 (8) |
C5—C4—C3—C2 | 0.5 (9) | C27—C28—C23—C22 | −177.9 (4) |
C12—C13—C14—C9 | 1.4 (9) | C25—C24—C23—C28 | −0.4 (8) |
C10—C9—C14—C13 | 1.2 (8) | C25—C24—C23—C22 | 178.5 (5) |
C8—C9—C14—C13 | −177.7 (5) | S1—C22—C23—C28 | −102.4 (5) |
C14—C13—C12—C11 | −3.2 (9) | S1—C22—C23—C24 | 78.7 (6) |
C10—C11—C12—C13 | 2.4 (9) | C27—C26—C25—C24 | 0.7 (9) |
C12—C11—C10—C9 | 0.2 (8) | C23—C24—C25—C26 | −0.5 (8) |
C14—C9—C10—C11 | −1.9 (8) | C20—C19—C18—C17 | 0.3 (8) |
C8—C9—C10—C11 | 176.9 (5) | C16—C17—C18—C19 | −2.0 (9) |
O1—S1—C22—C23 | 72.7 (5) | C6—C7—S2—O2 | 73.7 (4) |
C21—S1—C22—C23 | −178.1 (5) | C6—C7—S2—C8 | −177.5 (4) |
C16—C15—C20—C19 | −0.7 (8) | C9—C8—S2—O2 | −73.3 (4) |
C16—C15—C20—C21 | 177.7 (5) | C9—C8—S2—C7 | 177.8 (4) |
Experimental details
Crystal data | |
Chemical formula | C14H14OS |
Mr | 230.32 |
Crystal system, space group | Orthorhombic, Fdd2 |
Temperature (K) | 298 |
a, b, c (Å) | 17.882 (5), 53.150 (14), 10.233 (3) |
V (Å3) | 9726 (5) |
Z | 32 |
Radiation type | Mo Kα |
µ (mm−1) | 0.24 |
Crystal size (mm) | 0.36 × 0.28 × 0.15 |
Data collection | |
Diffractometer | Bruker APEXII CCD area-detector |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 14310, 5111, 2563 |
Rint | 0.042 |
(sin θ/λ)max (Å−1) | 0.667 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.057, 0.183, 0.97 |
No. of reflections | 5111 |
No. of parameters | 289 |
No. of restraints | 1 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.56, −0.19 |
Absolute structure | Flack (1983), 1074 Friedel pairs |
Absolute structure parameter | 0.00 (12) |
Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXS97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).
Sulfoxides have been widely used in the separation of palladium from other platinum-group metals by solvent extraction (Xu et al., 2006).A similar disulfoxide ligand 1,6-bis(benzylsulfinyl)hexane and its Copper(II) and Cadmium(II) dimeric complexes were obtained (Li et al.,2003). Crystals of dibenzyl sulfoxide show two independent molecules in the unit. There are asymmetry S—C bonds in a same molecule. The long axe of the crystals is directed along the b axis.