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

Wu, J.; Chen, C.

doi:10.1107/S1600536813032182

organic compounds

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https://doi.org/10.1107/S1600536813032182

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

Jinglan Wu ^a,^b and Chen Chen ^c ^*

^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.

CCDC reference: 971015

Related literature

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

Experimental

Crystal data

C₂₁H₂₆O₂SSe
M_r = 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 ) T_min = 0.590, T_max = 1.000
11048 measured reflections
4029 independent reflections
2554 reflections with I > 2σ(I)
R_int = 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
Δρ_max = 1.99 e Å⁻³
Δρ_min = −0.56 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	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); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; 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.

Supporting information

CCDC reference: 971015

Crystal structure: contains datablocks I, cd26300. DOI: https://doi.org/10.1107/S1600536813032182/hb7167sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536813032182/hb7167Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536813032182/hb7167Isup3.cml

checkCIF report

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.

Structure description top

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

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

	Fig. 1. The molecular structure of (I), with displacement ellipsoids drawn at the 50% probability level.
	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

C₂₁H₂₆O₂SSe	F(000) = 872
M_r = 421.44	D_x = 1.358 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2566 reflections
a = 12.869 (3) Å	θ = 5.3–46.3°
b = 19.445 (4) Å	µ = 1.93 mm⁻¹
c = 8.3702 (18) Å	T = 293 K
β = 100.280 (4)°	Block, colorless
V = 2061.0 (8) Å³	0.49 × 0.20 × 0.05 mm
Z = 4

Data collection top

Bruker SMART CCD diffractometer	4029 independent reflections
Radiation source: fine-focus sealed tube	2554 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.130
ω scans	θ_max = 26.0°, θ_min = 1.6°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −15→15
T_min = 0.590, T_max = 1.000	k = −23→23
11048 measured reflections	l = −7→10

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.086	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.230	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	w = 1/[σ²(F_o²) + (0.1331P)²] where P = (F_o² + 2F_c²)/3
4029 reflections	(Δ/σ)_max < 0.001
233 parameters	Δρ_max = 1.99 e Å⁻³
1 restraint	Δρ_min = −0.56 e Å⁻³

Crystal data top

C₂₁H₂₆O₂SSe	V = 2061.0 (8) Å³
M_r = 421.44	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 12.869 (3) Å	µ = 1.93 mm⁻¹
b = 19.445 (4) Å	T = 293 K
c = 8.3702 (18) Å	0.49 × 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)
T_min = 0.590, T_max = 1.000	R_int = 0.130
11048 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.086	1 restraint
wR(F²) = 0.230	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	Δρ_max = 1.99 e Å⁻³
4029 reflections	Δρ_min = −0.56 e Å⁻³
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

	x	y	z	U_iso*/U_eq
Se	0.75777 (6)	0.20048 (3)	0.48905 (9)	0.0587 (3)
S	0.58519 (11)	−0.00576 (8)	0.36854 (17)	0.0387 (4)
O1	0.7008 (3)	0.0066 (2)	0.6746 (5)	0.0426 (10)
O2	0.4924 (3)	−0.0048 (2)	0.2318 (5)	0.0492 (11)
C1	0.7020 (4)	0.1084 (3)	0.5070 (7)	0.0386 (13)
C2	0.6377 (4)	0.0827 (3)	0.3772 (7)	0.0373 (13)
C3	0.5957 (5)	0.1213 (3)	0.2208 (7)	0.0491 (15)
H3A	0.5782	0.0886	0.1325	0.059*
H3B	0.6504	0.1516	0.1951	0.059*
C4	0.4977 (6)	0.1639 (4)	0.2346 (8)	0.0600 (18)
H4A	0.4414	0.1332	0.2520	0.072*
H4B	0.5138	0.1940	0.3282	0.072*
C5	0.4604 (6)	0.2067 (4)	0.0850 (10)	0.071 (2)
H5A	0.4431	0.1764	−0.0080	0.086*
H5B	0.5177	0.2364	0.0662	0.086*
C6	0.3650 (8)	0.2508 (5)	0.0966 (13)	0.101 (3)
H6A	0.3091	0.2222	0.1211	0.151*
H6B	0.3419	0.2738	−0.0049	0.151*
H6C	0.3836	0.2843	0.1812	0.151*
C7	0.7396 (4)	0.0751 (3)	0.6735 (7)	0.0424 (14)
C8	0.8601 (5)	0.0684 (4)	0.7106 (9)	0.0636 (19)
H8A	0.8812	0.0461	0.8136	0.095*
H8B	0.8914	0.1134	0.7144	0.095*
H8C	0.8833	0.0417	0.6272	0.095*
C9	0.7015 (6)	0.1181 (4)	0.8048 (8)	0.0637 (19)
H9A	0.6257	0.1193	0.7848	0.096*
H9B	0.7283	0.1641	0.8027	0.096*
H9C	0.7265	0.0980	0.9094	0.096*
C10	0.6901 (4)	−0.0421 (3)	0.2807 (6)	0.0362 (12)
C11	0.7778 (5)	−0.0700 (3)	0.3809 (7)	0.0449 (14)
H11	0.7810	−0.0713	0.4928	0.054*
C12	0.8597 (5)	−0.0957 (4)	0.3142 (8)	0.0545 (17)
H12	0.9184	−0.1142	0.3813	0.065*
C13	0.8556 (5)	−0.0943 (3)	0.1477 (8)	0.0534 (17)
H13	0.9117	−0.1112	0.1032	0.064*
C14	0.7675 (5)	−0.0676 (4)	0.0483 (8)	0.0549 (17)
H14	0.7645	−0.0667	−0.0635	0.066*
C15	0.6836 (5)	−0.0422 (3)	0.1137 (7)	0.0467 (15)
H15	0.6237	−0.0253	0.0462	0.056*
C16	0.8780 (5)	0.1798 (3)	0.3887 (7)	0.0435 (14)
C17	0.9578 (6)	0.2285 (4)	0.4050 (8)	0.0568 (17)
H17	0.9518	0.2686	0.4630	0.068*
C18	1.0448 (7)	0.2181 (5)	0.3372 (10)	0.072 (2)
H18	1.0966	0.2518	0.3461	0.087*
C19	1.0569 (6)	0.1583 (4)	0.2558 (9)	0.066 (2)
H19	1.1176	0.1511	0.2119	0.080*
C20	0.9785 (6)	0.1086 (4)	0.2390 (9)	0.0629 (19)
H20	0.9865	0.0677	0.1848	0.075*
C21	0.8876 (5)	0.1202 (4)	0.3038 (8)	0.0549 (17)
H21	0.8336	0.0877	0.2898	0.066*
H1	0.644 (6)	0.000 (8)	0.710 (16)	0.19 (6)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Se	0.0632 (5)	0.0332 (4)	0.0829 (6)	−0.0006 (3)	0.0221 (4)	−0.0055 (3)
S	0.0302 (7)	0.0479 (9)	0.0366 (8)	−0.0027 (6)	0.0020 (6)	0.0017 (6)
O1	0.038 (2)	0.041 (2)	0.046 (2)	−0.0011 (18)	0.0017 (19)	0.0029 (17)
O2	0.027 (2)	0.073 (3)	0.044 (2)	0.0022 (19)	−0.0048 (18)	0.001 (2)
C1	0.033 (3)	0.033 (3)	0.050 (4)	0.007 (2)	0.010 (3)	−0.002 (2)
C2	0.032 (3)	0.041 (3)	0.039 (3)	0.008 (2)	0.007 (2)	0.001 (2)
C3	0.054 (4)	0.050 (4)	0.044 (4)	0.006 (3)	0.010 (3)	0.005 (3)
C4	0.062 (4)	0.062 (5)	0.055 (4)	0.026 (4)	0.008 (3)	0.010 (3)
C5	0.069 (5)	0.070 (5)	0.071 (5)	0.018 (4)	0.001 (4)	0.018 (4)
C6	0.098 (7)	0.097 (8)	0.101 (7)	0.053 (6)	0.002 (6)	0.017 (5)
C7	0.031 (3)	0.049 (4)	0.044 (3)	−0.006 (3)	0.000 (3)	−0.004 (3)
C8	0.045 (4)	0.073 (5)	0.068 (5)	−0.014 (3)	−0.003 (3)	0.009 (4)
C9	0.073 (5)	0.065 (5)	0.055 (4)	−0.010 (4)	0.015 (4)	−0.015 (3)
C10	0.032 (3)	0.035 (3)	0.040 (3)	−0.004 (2)	0.003 (2)	0.001 (2)
C11	0.047 (3)	0.047 (4)	0.038 (3)	0.006 (3)	0.000 (3)	0.002 (3)
C12	0.045 (4)	0.063 (4)	0.051 (4)	0.019 (3)	−0.003 (3)	0.002 (3)
C13	0.048 (4)	0.055 (4)	0.058 (4)	0.018 (3)	0.012 (3)	0.002 (3)
C14	0.064 (4)	0.064 (5)	0.037 (3)	0.016 (3)	0.010 (3)	−0.001 (3)
C15	0.043 (3)	0.051 (4)	0.042 (3)	0.010 (3)	−0.002 (3)	−0.003 (3)
C16	0.047 (3)	0.032 (3)	0.050 (4)	−0.002 (3)	0.006 (3)	0.005 (3)
C17	0.063 (4)	0.044 (4)	0.060 (4)	−0.012 (3)	0.001 (4)	−0.002 (3)
C18	0.067 (5)	0.072 (5)	0.075 (5)	−0.024 (4)	0.004 (4)	0.020 (4)
C19	0.054 (4)	0.081 (6)	0.067 (5)	−0.003 (4)	0.017 (4)	0.011 (4)
C20	0.061 (4)	0.064 (5)	0.064 (5)	0.008 (4)	0.014 (4)	0.004 (4)
C21	0.053 (4)	0.048 (4)	0.065 (4)	−0.008 (3)	0.015 (3)	−0.005 (3)

Geometric parameters (Å, º) top

Se—C16	1.930 (6)	C8—H8C	0.9600
Se—C1	1.945 (6)	C9—H9A	0.9600
S—O2	1.499 (4)	C9—H9B	0.9600
S—C10	1.793 (6)	C9—H9C	0.9600
S—C2	1.844 (6)	C10—C15	1.386 (8)
O1—C7	1.422 (7)	C10—C11	1.392 (8)
O1—H1	0.85 (2)	C11—C12	1.371 (9)
C1—C2	1.340 (8)	C11—H11	0.9300
C1—C7	1.534 (8)	C12—C13	1.385 (9)
C2—C3	1.523 (8)	C12—H12	0.9300
C3—C4	1.529 (9)	C13—C14	1.382 (9)
C3—H3A	0.9700	C13—H13	0.9300
C3—H3B	0.9700	C14—C15	1.385 (9)
C4—C5	1.510 (9)	C14—H14	0.9300
C4—H4A	0.9700	C15—H15	0.9300
C4—H4B	0.9700	C16—C21	1.378 (9)
C5—C6	1.514 (11)	C16—C17	1.385 (9)
C5—H5A	0.9700	C17—C18	1.357 (11)
C5—H5B	0.9700	C17—H17	0.9300
C6—H6A	0.9600	C18—C19	1.370 (12)
C6—H6B	0.9600	C18—H18	0.9300
C6—H6C	0.9600	C19—C20	1.387 (10)
C7—C9	1.530 (9)	C19—H19	0.9300
C7—C8	1.532 (8)	C20—C21	1.393 (9)
C8—H8A	0.9600	C20—H20	0.9300
C8—H8B	0.9600	C21—H21	0.9300

C16—Se—C1	100.2 (2)	H8A—C8—H8C	109.5
O2—S—C10	104.3 (2)	H8B—C8—H8C	109.5
O2—S—C2	104.7 (2)	C7—C9—H9A	109.5
C10—S—C2	95.0 (2)	C7—C9—H9B	109.5
C7—O1—H1	117 (10)	H9A—C9—H9B	109.5
C2—C1—C7	128.9 (5)	C7—C9—H9C	109.5
C2—C1—Se	117.6 (4)	H9A—C9—H9C	109.5
C7—C1—Se	113.5 (4)	H9B—C9—H9C	109.5
C1—C2—C3	125.9 (6)	C15—C10—C11	120.2 (5)
C1—C2—S	123.3 (4)	C15—C10—S	120.0 (4)
C3—C2—S	110.8 (4)	C11—C10—S	119.8 (4)
C2—C3—C4	111.9 (5)	C12—C11—C10	119.8 (6)
C2—C3—H3A	109.2	C12—C11—H11	120.1
C4—C3—H3A	109.2	C10—C11—H11	120.1
C2—C3—H3B	109.2	C11—C12—C13	120.6 (6)
C4—C3—H3B	109.2	C11—C12—H12	119.7
H3A—C3—H3B	107.9	C13—C12—H12	119.7
C5—C4—C3	112.4 (6)	C14—C13—C12	119.5 (6)
C5—C4—H4A	109.1	C14—C13—H13	120.2
C3—C4—H4A	109.1	C12—C13—H13	120.2
C5—C4—H4B	109.1	C13—C14—C15	120.6 (6)
C3—C4—H4B	109.1	C13—C14—H14	119.7
H4A—C4—H4B	107.9	C15—C14—H14	119.7
C4—C5—C6	113.6 (7)	C14—C15—C10	119.2 (5)
C4—C5—H5A	108.8	C14—C15—H15	120.4
C6—C5—H5A	108.8	C10—C15—H15	120.4
C4—C5—H5B	108.8	C21—C16—C17	119.5 (6)
C6—C5—H5B	108.8	C21—C16—Se	123.5 (5)
H5A—C5—H5B	107.7	C17—C16—Se	117.0 (5)
C5—C6—H6A	109.5	C18—C17—C16	120.7 (7)
C5—C6—H6B	109.5	C18—C17—H17	119.7
H6A—C6—H6B	109.5	C16—C17—H17	119.7
C5—C6—H6C	109.5	C17—C18—C19	120.7 (7)
H6A—C6—H6C	109.5	C17—C18—H18	119.6
H6B—C6—H6C	109.5	C19—C18—H18	119.6
O1—C7—C9	110.5 (5)	C18—C19—C20	119.7 (7)
O1—C7—C8	105.3 (5)	C18—C19—H19	120.2
C9—C7—C8	110.1 (6)	C20—C19—H19	120.2
O1—C7—C1	110.3 (4)	C19—C20—C21	119.7 (7)
C9—C7—C1	109.4 (5)	C19—C20—H20	120.2
C8—C7—C1	111.3 (5)	C21—C20—H20	120.2
C7—C8—H8A	109.5	C16—C21—C20	119.7 (6)
C7—C8—H8B	109.5	C16—C21—H21	120.1
H8A—C8—H8B	109.5	C20—C21—H21	120.1
C7—C8—H8C	109.5

C16—Se—C1—C2	−84.4 (5)	C2—S—C10—C15	−86.9 (5)
C16—Se—C1—C7	95.7 (4)	O2—S—C10—C11	−160.4 (5)
C7—C1—C2—C3	174.0 (5)	C2—S—C10—C11	93.0 (5)
Se—C1—C2—C3	−5.9 (8)	C15—C10—C11—C12	2.1 (9)
C7—C1—C2—S	−4.4 (8)	S—C10—C11—C12	−177.8 (5)
Se—C1—C2—S	175.7 (3)	C10—C11—C12—C13	−0.3 (10)
O2—S—C2—C1	161.7 (5)	C11—C12—C13—C14	−0.9 (11)
C10—S—C2—C1	−92.1 (5)	C12—C13—C14—C15	0.1 (11)
O2—S—C2—C3	−16.9 (4)	C13—C14—C15—C10	1.7 (10)
C10—S—C2—C3	89.3 (4)	C11—C10—C15—C14	−2.8 (9)
C1—C2—C3—C4	−83.7 (8)	S—C10—C15—C14	177.1 (5)
S—C2—C3—C4	94.9 (6)	C1—Se—C16—C21	21.1 (6)
C2—C3—C4—C5	175.6 (6)	C1—Se—C16—C17	−158.8 (5)
C3—C4—C5—C6	−178.6 (8)	C21—C16—C17—C18	0.5 (10)
C2—C1—C7—O1	3.4 (8)	Se—C16—C17—C18	−179.6 (5)
Se—C1—C7—O1	−176.6 (4)	C16—C17—C18—C19	−2.1 (11)
C2—C1—C7—C9	−118.2 (6)	C17—C18—C19—C20	1.6 (12)
Se—C1—C7—C9	61.7 (6)	C18—C19—C20—C21	0.6 (11)
C2—C1—C7—C8	119.9 (7)	C17—C16—C21—C20	1.7 (10)
Se—C1—C7—C8	−60.1 (6)	Se—C16—C21—C20	−178.2 (5)
O2—S—C10—C15	19.7 (5)	C19—C20—C21—C16	−2.2 (10)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	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.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	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.

Acknowledgements

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

References

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