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There are two independent mol­ecules in the asymmetric unit of the title compound, C14H14OS, which have asymmetric S-C bonds [1.791 (5) and 1.804 (5) Å in one mol­ecule and 1.798 (5) and 1.804 (5) Å in the other]. The long axes of the mol­ecules are directed along the crystallographic b axis.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536810052165/jh2245sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536810052165/jh2245Isup2.hkl
Contains datablock I

CCDC reference: 782396

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](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

Comment top

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.

Related literature top

For related structures, see: Li et al. (2003); Iitaka et al. (1986)

For related literature, see: Shriner et al. (1930); Xu et al. (2006).

Experimental top

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.)

Refinement top

(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).)

Structure description top

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).

Computing details top

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).

Figures top
[Figure 1] Fig. 1. Molecule structure of with displacement ellipsoids drawn at the 50% probability level.
Dibenzyl sulfoxide top
Crystal data top
C14H14OSF(000) = 3904
Mr = 230.32Dx = 1.258 Mg m3
Orthorhombic, Fdd2Mo Kα radiation, λ = 0.71073 Å
Hall symbol: F 2 -2dCell parameters from 2370 reflections
a = 17.882 (5) Åθ = 2.3–23.7°
b = 53.150 (14) ŵ = 0.24 mm1
c = 10.233 (3) ÅT = 298 K
V = 9726 (5) Å3Block, white
Z = 320.36 × 0.28 × 0.15 mm
Data collection top
Bruker APEXII CCD area-detector
diffractometer
2563 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.042
Graphite monochromatorθmax = 28.3°, θmin = 2.3°
phi and ω scansh = 2322
14310 measured reflectionsk = 5669
5111 independent reflectionsl = 1113
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)] = 0.057H-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 reflectionsΔρmax = 0.56 e Å3
289 parametersΔρmin = 0.19 e Å3
1 restraintAbsolute structure: Flack (1983), 1074 Friedel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.00 (12)
Crystal data top
C14H14OSV = 9726 (5) Å3
Mr = 230.32Z = 32
Orthorhombic, Fdd2Mo Kα radiation
a = 17.882 (5) ŵ = 0.24 mm1
b = 53.150 (14) ÅT = 298 K
c = 10.233 (3) Å0.36 × 0.28 × 0.15 mm
Data collection top
Bruker APEXII CCD area-detector
diffractometer
2563 reflections with I > 2σ(I)
14310 measured reflectionsRint = 0.042
5111 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.057H-atom parameters constrained
wR(F2) = 0.183Δρmax = 0.56 e Å3
S = 0.97Δρmin = 0.19 e Å3
5111 reflectionsAbsolute structure: Flack (1983), 1074 Friedel pairs
289 parametersAbsolute structure parameter: 0.00 (12)
1 restraint
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
S10.40616 (7)0.12486 (3)0.42542 (10)0.0541 (3)
C60.1374 (2)0.07435 (9)0.7186 (5)0.0511 (13)
C90.1385 (3)0.17549 (9)0.7183 (5)0.0547 (13)
C70.1315 (3)0.10024 (9)0.7775 (5)0.0657 (13)
H7A0.17130.10240.84100.079*
H7B0.08420.10170.82330.079*
C80.1322 (3)0.14959 (9)0.7780 (5)0.0637 (13)
H8A0.08500.14830.82410.076*
H8B0.17200.14740.84120.076*
C40.0819 (3)0.03513 (11)0.6580 (6)0.0878 (18)
H40.04000.02480.65110.105*
C130.2163 (3)0.20854 (11)0.6307 (6)0.0814 (16)
H130.26300.21440.60450.098*
C10.2051 (3)0.06488 (10)0.6809 (6)0.0693 (13)
H10.24750.07490.68940.083*
C20.2122 (3)0.04126 (10)0.6312 (6)0.0796 (16)
H20.25900.03550.60500.096*
C50.0754 (3)0.05917 (11)0.7057 (6)0.0747 (15)
H50.02860.06530.72970.090*
C30.1526 (4)0.02621 (10)0.6196 (6)0.0782 (17)
H30.15780.01000.58650.094*
C110.0846 (3)0.21459 (11)0.6523 (6)0.0790 (17)
H110.04250.22470.64140.095*
C140.2086 (3)0.18479 (9)0.6809 (6)0.0697 (14)
H140.25070.17470.69030.084*
C120.1542 (3)0.22363 (10)0.6195 (6)0.0774 (17)
H120.15930.24010.58960.093*
C100.0773 (3)0.19068 (10)0.7010 (5)0.0707 (15)
H100.03010.18470.72270.085*
C170.4166 (3)0.02607 (10)0.3893 (7)0.0738 (16)
H170.42940.00960.36780.089*
C260.4207 (3)0.22365 (10)0.3836 (7)0.0742 (16)
H260.43540.23990.36090.089*
C150.4119 (3)0.05920 (10)0.5446 (6)0.0726 (15)
H150.42250.06530.62770.087*
C220.3498 (3)0.14955 (10)0.4925 (6)0.0674 (14)
H22A0.29870.14740.46300.081*
H22B0.35010.14820.58700.081*
C240.3599 (3)0.18525 (10)0.3314 (6)0.0695 (15)
H240.33340.17550.27180.083*
C280.4160 (3)0.19012 (10)0.5414 (6)0.0737 (15)
H280.42830.18390.62360.088*
C190.3607 (3)0.06475 (10)0.3319 (6)0.0697 (14)
H190.33660.07490.27100.084*
C200.3754 (3)0.07420 (9)0.4574 (5)0.0525 (13)
C160.4335 (3)0.03512 (10)0.5121 (6)0.0823 (17)
H160.45890.02510.57200.099*
C270.4374 (3)0.21400 (10)0.5059 (7)0.0844 (18)
H270.46360.22390.56520.101*
C210.3494 (3)0.10017 (9)0.4944 (6)0.0655 (14)
H21A0.34980.10170.58880.079*
H21B0.29820.10230.46520.079*
C230.3763 (3)0.17547 (9)0.4545 (5)0.0537 (13)
C250.3822 (3)0.20898 (11)0.2968 (6)0.0818 (16)
H250.37110.21510.21400.098*
C180.3813 (3)0.04094 (12)0.2979 (6)0.0823 (16)
H180.37160.03480.21440.099*
O10.47890 (18)0.12488 (7)0.4984 (4)0.0831 (11)
O20.0644 (2)0.12505 (7)0.5840 (4)0.0850 (11)
S20.13762 (7)0.12488 (3)0.65757 (9)0.0548 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0557 (6)0.0490 (6)0.0575 (8)0.0010 (6)0.0076 (5)0.0000 (7)
C60.057 (3)0.044 (3)0.053 (3)0.003 (2)0.002 (2)0.007 (2)
C90.064 (3)0.048 (3)0.052 (3)0.005 (2)0.010 (2)0.010 (3)
C70.080 (3)0.064 (3)0.053 (3)0.005 (3)0.002 (3)0.006 (3)
C80.083 (3)0.061 (3)0.047 (3)0.000 (2)0.004 (3)0.006 (2)
C40.100 (4)0.077 (4)0.086 (4)0.037 (3)0.024 (4)0.003 (4)
C130.082 (4)0.076 (4)0.087 (4)0.009 (3)0.000 (3)0.002 (3)
C10.064 (3)0.066 (3)0.078 (4)0.005 (2)0.002 (3)0.009 (3)
C20.088 (4)0.066 (4)0.085 (4)0.009 (3)0.007 (3)0.007 (3)
C50.063 (3)0.079 (4)0.082 (4)0.002 (3)0.017 (3)0.006 (3)
C30.121 (5)0.048 (4)0.066 (4)0.007 (3)0.004 (4)0.003 (3)
C110.079 (4)0.070 (4)0.088 (4)0.022 (3)0.019 (4)0.015 (3)
C140.061 (3)0.068 (3)0.080 (4)0.009 (2)0.007 (3)0.009 (3)
C120.114 (5)0.050 (4)0.068 (4)0.005 (3)0.006 (3)0.007 (3)
C100.057 (3)0.077 (4)0.079 (4)0.004 (2)0.008 (3)0.011 (3)
C170.073 (3)0.054 (4)0.094 (5)0.002 (3)0.010 (3)0.001 (3)
C260.074 (3)0.051 (4)0.098 (5)0.002 (3)0.009 (3)0.005 (3)
C150.072 (3)0.080 (4)0.065 (3)0.001 (3)0.014 (3)0.008 (3)
C220.061 (3)0.066 (4)0.074 (4)0.005 (2)0.014 (3)0.008 (3)
C240.072 (3)0.059 (3)0.077 (4)0.004 (2)0.007 (3)0.011 (3)
C280.074 (3)0.069 (4)0.078 (4)0.011 (3)0.014 (3)0.014 (3)
C190.075 (3)0.064 (3)0.070 (4)0.002 (3)0.013 (3)0.009 (3)
C200.051 (3)0.048 (3)0.058 (3)0.005 (2)0.004 (2)0.006 (3)
C160.081 (4)0.072 (4)0.094 (5)0.008 (3)0.010 (4)0.021 (3)
C270.074 (4)0.069 (4)0.110 (5)0.001 (3)0.016 (4)0.033 (3)
C210.063 (3)0.063 (3)0.071 (4)0.002 (2)0.013 (3)0.001 (3)
C230.052 (3)0.046 (3)0.063 (3)0.007 (2)0.006 (2)0.007 (3)
C250.091 (4)0.074 (4)0.080 (4)0.015 (3)0.002 (3)0.005 (3)
C180.096 (4)0.077 (4)0.073 (4)0.008 (3)0.003 (3)0.006 (3)
O10.0486 (17)0.083 (2)0.117 (3)0.0017 (15)0.011 (2)0.004 (3)
O20.088 (3)0.099 (3)0.067 (2)0.001 (2)0.034 (2)0.003 (2)
S20.0703 (8)0.0508 (6)0.0434 (6)0.0005 (6)0.0020 (6)0.0014 (7)
Geometric parameters (Å, º) top
S1—O11.500 (3)C10—H100.9300
S1—C221.791 (5)C17—C181.378 (8)
S1—C211.804 (5)C17—C161.379 (8)
C6—C11.367 (6)C17—H170.9300
C6—C51.378 (6)C26—C251.368 (8)
C6—C71.506 (6)C26—C271.385 (8)
C9—C101.371 (6)C26—H260.9300
C9—C141.401 (6)C15—C201.363 (7)
C9—C81.510 (6)C15—C161.377 (7)
C7—S21.798 (5)C15—H150.9300
C7—H7A0.9700C22—C231.508 (7)
C7—H7B0.9700C22—H22A0.9700
C8—S21.804 (5)C22—H22B0.9700
C8—H8A0.9700C24—C251.369 (7)
C8—H8B0.9700C24—C231.395 (7)
C4—C51.373 (8)C24—H240.9300
C4—C31.405 (8)C28—C271.374 (8)
C4—H40.9300C28—C231.379 (7)
C13—C141.370 (7)C28—H280.9300
C13—C121.375 (7)C19—C181.363 (7)
C13—H130.9300C19—C201.404 (7)
C1—C21.360 (7)C19—H190.9300
C1—H10.9300C20—C211.505 (6)
C2—C31.338 (7)C16—H160.9300
C2—H20.9300C27—H270.9300
C5—H50.9300C21—H21A0.9700
C3—H30.9300C21—H21B0.9700
C11—C101.371 (8)C25—H250.9300
C11—C121.376 (8)C18—H180.9300
C11—H110.9300O2—S21.511 (3)
C14—H140.9300S2—C71.798 (5)
C12—H120.9300S2—C81.804 (5)
O1—S1—C22107.2 (2)C18—C17—C16121.3 (6)
O1—S1—C21107.1 (2)C18—C17—H17119.4
C22—S1—C2193.8 (2)C16—C17—H17119.4
C1—C6—C5118.1 (5)C25—C26—C27119.0 (5)
C1—C6—C7120.8 (5)C25—C26—H26120.5
C5—C6—C7121.1 (5)C27—C26—H26120.5
C10—C9—C14118.1 (5)C20—C15—C16121.3 (6)
C10—C9—C8122.0 (5)C20—C15—H15119.3
C14—C9—C8119.9 (4)C16—C15—H15119.3
C6—C7—S2112.8 (4)C23—C22—S1113.2 (3)
C6—C7—H7A109.0C23—C22—H22A108.9
S2—C7—H7A109.0S1—C22—H22A108.9
C6—C7—H7B109.0C23—C22—H22B108.9
S2—C7—H7B109.0S1—C22—H22B108.9
H7A—C7—H7B107.8H22A—C22—H22B107.7
C9—C8—S2112.6 (4)C25—C24—C23121.0 (6)
C9—C8—H8A109.1C25—C24—H24119.5
S2—C8—H8A109.1C23—C24—H24119.5
C9—C8—H8B109.1C27—C28—C23119.6 (6)
S2—C8—H8B109.1C27—C28—H28120.2
H8A—C8—H8B107.8C23—C28—H28120.2
C5—C4—C3119.4 (5)C18—C19—C20121.0 (5)
C5—C4—H4120.3C18—C19—H19119.5
C3—C4—H4120.3C20—C19—H19119.5
C14—C13—C12119.2 (5)C15—C20—C19118.6 (5)
C14—C13—H13120.4C15—C20—C21121.3 (5)
C12—C13—H13120.4C19—C20—C21120.0 (5)
C2—C1—C6121.9 (5)C15—C16—C17118.9 (5)
C2—C1—H1119.1C15—C16—H16120.6
C6—C1—H1119.1C17—C16—H16120.6
C3—C2—C1120.7 (5)C28—C27—C26121.4 (5)
C3—C2—H2119.7C28—C27—H27119.3
C1—C2—H2119.7C26—C27—H27119.3
C4—C5—C6120.7 (5)C20—C21—S1113.2 (3)
C4—C5—H5119.7C20—C21—H21A108.9
C6—C5—H5119.7S1—C21—H21A108.9
C2—C3—C4119.3 (5)C20—C21—H21B108.9
C2—C3—H3120.3S1—C21—H21B108.9
C4—C3—H3120.3H21A—C21—H21B107.7
C10—C11—C12119.8 (5)C28—C23—C24118.7 (5)
C10—C11—H11120.1C28—C23—C22120.8 (5)
C12—C11—H11120.1C24—C23—C22120.5 (5)
C13—C14—C9121.1 (5)C26—C25—C24120.2 (6)
C13—C14—H14119.4C26—C25—H25119.9
C9—C14—H14119.4C24—C25—H25119.9
C13—C12—C11120.5 (6)C19—C18—C17118.9 (6)
C13—C12—H12119.8C19—C18—H18120.6
C11—C12—H12119.8C17—C18—H18120.6
C11—C10—C9121.1 (5)O2—S2—C7107.0 (2)
C11—C10—H10119.4O2—S2—C8106.8 (2)
C9—C10—H10119.4C7—S2—C893.5 (2)
C1—C6—C7—S277.1 (6)C18—C19—C20—C151.0 (8)
C5—C6—C7—S2105.4 (5)C18—C19—C20—C21177.4 (5)
C10—C9—C8—S2103.3 (5)C20—C15—C16—C170.9 (8)
C14—C9—C8—S277.8 (6)C18—C17—C16—C152.3 (9)
C5—C6—C1—C20.4 (8)C23—C28—C27—C260.8 (8)
C7—C6—C1—C2177.9 (5)C25—C26—C27—C280.1 (9)
C6—C1—C2—C31.2 (9)C15—C20—C21—S1105.3 (5)
C3—C4—C5—C61.2 (9)C19—C20—C21—S176.3 (6)
C1—C6—C5—C40.8 (8)O1—S1—C21—C2072.8 (5)
C7—C6—C5—C4176.7 (5)C22—S1—C21—C20177.8 (4)
C1—C2—C3—C40.7 (9)C27—C28—C23—C241.0 (8)
C5—C4—C3—C20.5 (9)C27—C28—C23—C22177.9 (4)
C12—C13—C14—C91.4 (9)C25—C24—C23—C280.4 (8)
C10—C9—C14—C131.2 (8)C25—C24—C23—C22178.5 (5)
C8—C9—C14—C13177.7 (5)S1—C22—C23—C28102.4 (5)
C14—C13—C12—C113.2 (9)S1—C22—C23—C2478.7 (6)
C10—C11—C12—C132.4 (9)C27—C26—C25—C240.7 (9)
C12—C11—C10—C90.2 (8)C23—C24—C25—C260.5 (8)
C14—C9—C10—C111.9 (8)C20—C19—C18—C170.3 (8)
C8—C9—C10—C11176.9 (5)C16—C17—C18—C192.0 (9)
O1—S1—C22—C2372.7 (5)C6—C7—S2—O273.7 (4)
C21—S1—C22—C23178.1 (5)C6—C7—S2—C8177.5 (4)
C16—C15—C20—C190.7 (8)C9—C8—S2—O273.3 (4)
C16—C15—C20—C21177.7 (5)C9—C8—S2—C7177.8 (4)

Experimental details

Crystal data
Chemical formulaC14H14OS
Mr230.32
Crystal system, space groupOrthorhombic, Fdd2
Temperature (K)298
a, b, c (Å)17.882 (5), 53.150 (14), 10.233 (3)
V3)9726 (5)
Z32
Radiation typeMo Kα
µ (mm1)0.24
Crystal size (mm)0.36 × 0.28 × 0.15
Data collection
DiffractometerBruker APEXII CCD area-detector
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
14310, 5111, 2563
Rint0.042
(sin θ/λ)max1)0.667
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.057, 0.183, 0.97
No. of reflections5111
No. of parameters289
No. of restraints1
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.56, 0.19
Absolute structureFlack (1983), 1074 Friedel pairs
Absolute structure parameter0.00 (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).

 

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