organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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ISSN: 2056-9890

(E)-2-Methyl-3-phenyl­selanyl-4-(phenyl­sulfin­yl)oct-3-en-2-ol

aCollege of Biotechnology and Pharmaceutical Engineering, Nanjing University of Technology, Nanjing 210009, People's Republic of China, bNational Engineering Technique Research Center for Biotechnology, Nanjing 211816, People's Republic of China, and cResearch Institute of Benzene Chemical, Research Institute of Nanjing Chemical Industry Group, No. 699 Geguan Road, Dachang, Nanjing 210044, People's Republic of China
*Correspondence e-mail: cccnhy@163.com

(Received 24 November 2013; accepted 26 November 2013; online 4 December 2013)

In the title compound, C21H26O2SSe, the S atom adopts a pyramidal geometry (bond-angle sum = 304°) and the n-butyl chain shows an extended conformation. An intra­molecular C—H⋯O hydrogen bond closes an S(8) ring. In the crystal, inversion dimers are formed with molecules linked by pairs of O—H⋯O=S hydrogen bonds, generating R22(14) loops. Weak C—H⋯O inter­actions also occur.

Related literature

For background to the title compound, see: Uma et al. (2003[Uma, R., Crevisy, C. & Gree, R. (2003). Chem. Rev. 103, 27-52.]). For the synthesis, see: He et al. (2007[He, G., Zhou, C., Fu, C. & Ma, S. (2007). Tetrahedron, 63, 3800-3805.]).

[Scheme 1]

Experimental

Crystal data
  • C21H26O2SSe

  • Mr = 421.44

  • Monoclinic, P 21 /c

  • a = 12.869 (3) Å

  • b = 19.445 (4) Å

  • c = 8.3702 (18) Å

  • β = 100.280 (4)°

  • V = 2061.0 (8) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 1.93 mm−1

  • T = 293 K

  • 0.49 × 0.20 × 0.05 mm

Data collection
  • Bruker SMART CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2001[Bruker (2001). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.590, Tmax = 1.000

  • 11048 measured reflections

  • 4029 independent reflections

  • 2554 reflections with I > 2σ(I)

  • Rint = 0.130

Refinement
  • R[F2 > 2σ(F2)] = 0.086

  • wR(F2) = 0.230

  • S = 1.01

  • 4029 reflections

  • 233 parameters

  • 1 restraint

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 1.99 e Å−3

  • Δρmin = −0.56 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
O1—H1⋯O2i 0.85 (9) 1.91 (8) 2.737 (6) 167 (10)
C11—H11⋯O1 0.93 2.50 3.180 (7) 130
C15—H15⋯O2ii 0.93 2.60 3.463 (7) 155
Symmetry codes: (i) -x+1, -y, -z+1; (ii) -x+1, -y, -z.

Data collection: SMART (Bruker, 2001[Bruker (2001). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2001[Bruker (2001). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.

Supporting information


Related literature top

For background to the title compound, see: Uma et al. (2003). For the synthesis, see: He et al. (2007).

Experimental top

The title compund was synthesized according to the published procedure (He et al., 2007). Colourless blocks were obtained by dissolving it (0.5 g) in tetrahydrofuran (20 ml) and evaporating the solvent slowly at room temperature for about 10 d.

Refinement top

H atoms were positioned geometrically and refined as riding groups, with C—H = 0.93 Å for aromatic H, and constrained to ride on their parent atoms, with Uiso(H) = xUeq(C), where x = 1.2 for aromatic H, and x = 1.5 for other H.

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of (I), with displacement ellipsoids drawn at the 50% probability level.
[Figure 2] Fig. 2. A packing diagram of (I). O—H···O and C—H···O hydrogen bonds are shown as dashed lines.
(E)-2-Methyl-3-phenylselanyl-4-(phenylsulfinyl)oct-3-en-2-ol top
Crystal data top
C21H26O2SSeF(000) = 872
Mr = 421.44Dx = 1.358 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 2566 reflections
a = 12.869 (3) Åθ = 5.3–46.3°
b = 19.445 (4) ŵ = 1.93 mm1
c = 8.3702 (18) ÅT = 293 K
β = 100.280 (4)°Block, colorless
V = 2061.0 (8) Å30.49 × 0.20 × 0.05 mm
Z = 4
Data collection top
Bruker SMART CCD
diffractometer
4029 independent reflections
Radiation source: fine-focus sealed tube2554 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.130
ω scansθmax = 26.0°, θmin = 1.6°
Absorption correction: multi-scan
(SADABS; Bruker, 2001)
h = 1515
Tmin = 0.590, Tmax = 1.000k = 2323
11048 measured reflectionsl = 710
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)] = 0.086Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.230H atoms treated by a mixture of independent and constrained refinement
S = 1.01 w = 1/[σ2(Fo2) + (0.1331P)2]
where P = (Fo2 + 2Fc2)/3
4029 reflections(Δ/σ)max < 0.001
233 parametersΔρmax = 1.99 e Å3
1 restraintΔρmin = 0.56 e Å3
Crystal data top
C21H26O2SSeV = 2061.0 (8) Å3
Mr = 421.44Z = 4
Monoclinic, P21/cMo Kα radiation
a = 12.869 (3) ŵ = 1.93 mm1
b = 19.445 (4) ÅT = 293 K
c = 8.3702 (18) Å0.49 × 0.20 × 0.05 mm
β = 100.280 (4)°
Data collection top
Bruker SMART CCD
diffractometer
4029 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2001)
2554 reflections with I > 2σ(I)
Tmin = 0.590, Tmax = 1.000Rint = 0.130
11048 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0861 restraint
wR(F2) = 0.230H atoms treated by a mixture of independent and constrained refinement
S = 1.01Δρmax = 1.99 e Å3
4029 reflectionsΔρmin = 0.56 e Å3
233 parameters
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
Se0.75777 (6)0.20048 (3)0.48905 (9)0.0587 (3)
S0.58519 (11)0.00576 (8)0.36854 (17)0.0387 (4)
O10.7008 (3)0.0066 (2)0.6746 (5)0.0426 (10)
O20.4924 (3)0.0048 (2)0.2318 (5)0.0492 (11)
C10.7020 (4)0.1084 (3)0.5070 (7)0.0386 (13)
C20.6377 (4)0.0827 (3)0.3772 (7)0.0373 (13)
C30.5957 (5)0.1213 (3)0.2208 (7)0.0491 (15)
H3A0.57820.08860.13250.059*
H3B0.65040.15160.19510.059*
C40.4977 (6)0.1639 (4)0.2346 (8)0.0600 (18)
H4A0.44140.13320.25200.072*
H4B0.51380.19400.32820.072*
C50.4604 (6)0.2067 (4)0.0850 (10)0.071 (2)
H5A0.44310.17640.00800.086*
H5B0.51770.23640.06620.086*
C60.3650 (8)0.2508 (5)0.0966 (13)0.101 (3)
H6A0.30910.22220.12110.151*
H6B0.34190.27380.00490.151*
H6C0.38360.28430.18120.151*
C70.7396 (4)0.0751 (3)0.6735 (7)0.0424 (14)
C80.8601 (5)0.0684 (4)0.7106 (9)0.0636 (19)
H8A0.88120.04610.81360.095*
H8B0.89140.11340.71440.095*
H8C0.88330.04170.62720.095*
C90.7015 (6)0.1181 (4)0.8048 (8)0.0637 (19)
H9A0.62570.11930.78480.096*
H9B0.72830.16410.80270.096*
H9C0.72650.09800.90940.096*
C100.6901 (4)0.0421 (3)0.2807 (6)0.0362 (12)
C110.7778 (5)0.0700 (3)0.3809 (7)0.0449 (14)
H110.78100.07130.49280.054*
C120.8597 (5)0.0957 (4)0.3142 (8)0.0545 (17)
H120.91840.11420.38130.065*
C130.8556 (5)0.0943 (3)0.1477 (8)0.0534 (17)
H130.91170.11120.10320.064*
C140.7675 (5)0.0676 (4)0.0483 (8)0.0549 (17)
H140.76450.06670.06350.066*
C150.6836 (5)0.0422 (3)0.1137 (7)0.0467 (15)
H150.62370.02530.04620.056*
C160.8780 (5)0.1798 (3)0.3887 (7)0.0435 (14)
C170.9578 (6)0.2285 (4)0.4050 (8)0.0568 (17)
H170.95180.26860.46300.068*
C181.0448 (7)0.2181 (5)0.3372 (10)0.072 (2)
H181.09660.25180.34610.087*
C191.0569 (6)0.1583 (4)0.2558 (9)0.066 (2)
H191.11760.15110.21190.080*
C200.9785 (6)0.1086 (4)0.2390 (9)0.0629 (19)
H200.98650.06770.18480.075*
C210.8876 (5)0.1202 (4)0.3038 (8)0.0549 (17)
H210.83360.08770.28980.066*
H10.644 (6)0.000 (8)0.710 (16)0.19 (6)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Se0.0632 (5)0.0332 (4)0.0829 (6)0.0006 (3)0.0221 (4)0.0055 (3)
S0.0302 (7)0.0479 (9)0.0366 (8)0.0027 (6)0.0020 (6)0.0017 (6)
O10.038 (2)0.041 (2)0.046 (2)0.0011 (18)0.0017 (19)0.0029 (17)
O20.027 (2)0.073 (3)0.044 (2)0.0022 (19)0.0048 (18)0.001 (2)
C10.033 (3)0.033 (3)0.050 (4)0.007 (2)0.010 (3)0.002 (2)
C20.032 (3)0.041 (3)0.039 (3)0.008 (2)0.007 (2)0.001 (2)
C30.054 (4)0.050 (4)0.044 (4)0.006 (3)0.010 (3)0.005 (3)
C40.062 (4)0.062 (5)0.055 (4)0.026 (4)0.008 (3)0.010 (3)
C50.069 (5)0.070 (5)0.071 (5)0.018 (4)0.001 (4)0.018 (4)
C60.098 (7)0.097 (8)0.101 (7)0.053 (6)0.002 (6)0.017 (5)
C70.031 (3)0.049 (4)0.044 (3)0.006 (3)0.000 (3)0.004 (3)
C80.045 (4)0.073 (5)0.068 (5)0.014 (3)0.003 (3)0.009 (4)
C90.073 (5)0.065 (5)0.055 (4)0.010 (4)0.015 (4)0.015 (3)
C100.032 (3)0.035 (3)0.040 (3)0.004 (2)0.003 (2)0.001 (2)
C110.047 (3)0.047 (4)0.038 (3)0.006 (3)0.000 (3)0.002 (3)
C120.045 (4)0.063 (4)0.051 (4)0.019 (3)0.003 (3)0.002 (3)
C130.048 (4)0.055 (4)0.058 (4)0.018 (3)0.012 (3)0.002 (3)
C140.064 (4)0.064 (5)0.037 (3)0.016 (3)0.010 (3)0.001 (3)
C150.043 (3)0.051 (4)0.042 (3)0.010 (3)0.002 (3)0.003 (3)
C160.047 (3)0.032 (3)0.050 (4)0.002 (3)0.006 (3)0.005 (3)
C170.063 (4)0.044 (4)0.060 (4)0.012 (3)0.001 (4)0.002 (3)
C180.067 (5)0.072 (5)0.075 (5)0.024 (4)0.004 (4)0.020 (4)
C190.054 (4)0.081 (6)0.067 (5)0.003 (4)0.017 (4)0.011 (4)
C200.061 (4)0.064 (5)0.064 (5)0.008 (4)0.014 (4)0.004 (4)
C210.053 (4)0.048 (4)0.065 (4)0.008 (3)0.015 (3)0.005 (3)
Geometric parameters (Å, º) top
Se—C161.930 (6)C8—H8C0.9600
Se—C11.945 (6)C9—H9A0.9600
S—O21.499 (4)C9—H9B0.9600
S—C101.793 (6)C9—H9C0.9600
S—C21.844 (6)C10—C151.386 (8)
O1—C71.422 (7)C10—C111.392 (8)
O1—H10.85 (2)C11—C121.371 (9)
C1—C21.340 (8)C11—H110.9300
C1—C71.534 (8)C12—C131.385 (9)
C2—C31.523 (8)C12—H120.9300
C3—C41.529 (9)C13—C141.382 (9)
C3—H3A0.9700C13—H130.9300
C3—H3B0.9700C14—C151.385 (9)
C4—C51.510 (9)C14—H140.9300
C4—H4A0.9700C15—H150.9300
C4—H4B0.9700C16—C211.378 (9)
C5—C61.514 (11)C16—C171.385 (9)
C5—H5A0.9700C17—C181.357 (11)
C5—H5B0.9700C17—H170.9300
C6—H6A0.9600C18—C191.370 (12)
C6—H6B0.9600C18—H180.9300
C6—H6C0.9600C19—C201.387 (10)
C7—C91.530 (9)C19—H190.9300
C7—C81.532 (8)C20—C211.393 (9)
C8—H8A0.9600C20—H200.9300
C8—H8B0.9600C21—H210.9300
C16—Se—C1100.2 (2)H8A—C8—H8C109.5
O2—S—C10104.3 (2)H8B—C8—H8C109.5
O2—S—C2104.7 (2)C7—C9—H9A109.5
C10—S—C295.0 (2)C7—C9—H9B109.5
C7—O1—H1117 (10)H9A—C9—H9B109.5
C2—C1—C7128.9 (5)C7—C9—H9C109.5
C2—C1—Se117.6 (4)H9A—C9—H9C109.5
C7—C1—Se113.5 (4)H9B—C9—H9C109.5
C1—C2—C3125.9 (6)C15—C10—C11120.2 (5)
C1—C2—S123.3 (4)C15—C10—S120.0 (4)
C3—C2—S110.8 (4)C11—C10—S119.8 (4)
C2—C3—C4111.9 (5)C12—C11—C10119.8 (6)
C2—C3—H3A109.2C12—C11—H11120.1
C4—C3—H3A109.2C10—C11—H11120.1
C2—C3—H3B109.2C11—C12—C13120.6 (6)
C4—C3—H3B109.2C11—C12—H12119.7
H3A—C3—H3B107.9C13—C12—H12119.7
C5—C4—C3112.4 (6)C14—C13—C12119.5 (6)
C5—C4—H4A109.1C14—C13—H13120.2
C3—C4—H4A109.1C12—C13—H13120.2
C5—C4—H4B109.1C13—C14—C15120.6 (6)
C3—C4—H4B109.1C13—C14—H14119.7
H4A—C4—H4B107.9C15—C14—H14119.7
C4—C5—C6113.6 (7)C14—C15—C10119.2 (5)
C4—C5—H5A108.8C14—C15—H15120.4
C6—C5—H5A108.8C10—C15—H15120.4
C4—C5—H5B108.8C21—C16—C17119.5 (6)
C6—C5—H5B108.8C21—C16—Se123.5 (5)
H5A—C5—H5B107.7C17—C16—Se117.0 (5)
C5—C6—H6A109.5C18—C17—C16120.7 (7)
C5—C6—H6B109.5C18—C17—H17119.7
H6A—C6—H6B109.5C16—C17—H17119.7
C5—C6—H6C109.5C17—C18—C19120.7 (7)
H6A—C6—H6C109.5C17—C18—H18119.6
H6B—C6—H6C109.5C19—C18—H18119.6
O1—C7—C9110.5 (5)C18—C19—C20119.7 (7)
O1—C7—C8105.3 (5)C18—C19—H19120.2
C9—C7—C8110.1 (6)C20—C19—H19120.2
O1—C7—C1110.3 (4)C19—C20—C21119.7 (7)
C9—C7—C1109.4 (5)C19—C20—H20120.2
C8—C7—C1111.3 (5)C21—C20—H20120.2
C7—C8—H8A109.5C16—C21—C20119.7 (6)
C7—C8—H8B109.5C16—C21—H21120.1
H8A—C8—H8B109.5C20—C21—H21120.1
C7—C8—H8C109.5
C16—Se—C1—C284.4 (5)C2—S—C10—C1586.9 (5)
C16—Se—C1—C795.7 (4)O2—S—C10—C11160.4 (5)
C7—C1—C2—C3174.0 (5)C2—S—C10—C1193.0 (5)
Se—C1—C2—C35.9 (8)C15—C10—C11—C122.1 (9)
C7—C1—C2—S4.4 (8)S—C10—C11—C12177.8 (5)
Se—C1—C2—S175.7 (3)C10—C11—C12—C130.3 (10)
O2—S—C2—C1161.7 (5)C11—C12—C13—C140.9 (11)
C10—S—C2—C192.1 (5)C12—C13—C14—C150.1 (11)
O2—S—C2—C316.9 (4)C13—C14—C15—C101.7 (10)
C10—S—C2—C389.3 (4)C11—C10—C15—C142.8 (9)
C1—C2—C3—C483.7 (8)S—C10—C15—C14177.1 (5)
S—C2—C3—C494.9 (6)C1—Se—C16—C2121.1 (6)
C2—C3—C4—C5175.6 (6)C1—Se—C16—C17158.8 (5)
C3—C4—C5—C6178.6 (8)C21—C16—C17—C180.5 (10)
C2—C1—C7—O13.4 (8)Se—C16—C17—C18179.6 (5)
Se—C1—C7—O1176.6 (4)C16—C17—C18—C192.1 (11)
C2—C1—C7—C9118.2 (6)C17—C18—C19—C201.6 (12)
Se—C1—C7—C961.7 (6)C18—C19—C20—C210.6 (11)
C2—C1—C7—C8119.9 (7)C17—C16—C21—C201.7 (10)
Se—C1—C7—C860.1 (6)Se—C16—C21—C20178.2 (5)
O2—S—C10—C1519.7 (5)C19—C20—C21—C162.2 (10)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···O2i0.85 (9)1.91 (8)2.737 (6)167 (10)
C11—H11···O10.932.503.180 (7)130
C15—H15···O2ii0.932.603.463 (7)155
Symmetry codes: (i) x+1, y, z+1; (ii) x+1, y, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···O2i0.85 (9)1.91 (8)2.737 (6)167 (10)
C11—H11···O10.932.503.180 (7)130
C15—H15···O2ii0.932.603.463 (7)155
Symmetry codes: (i) x+1, y, z+1; (ii) x+1, y, z.
 

Acknowledgements

The authors thank the Center of Test and Analysis, Nanjing University, for the data collection.

References

First citationBruker (2001). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
First citationHe, G., Zhou, C., Fu, C. & Ma, S. (2007). Tetrahedron, 63, 3800–3805.  Web of Science CSD CrossRef CAS
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals
First citationUma, R., Crevisy, C. & Gree, R. (2003). Chem. Rev. 103, 27–52.  Web of Science CrossRef PubMed CAS

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