(Z)-2-[(4-Methyl-phen-yl)sulfon-yl]-1,2-diphenyl-ethene-selenol.

In the title compound, C(21)H(18)O(2)SSe, the dihedral angle between the cis phenyl rings is 64.3 (1)° and those between the toluene and the phenyl rings are 21.1 (2) and 72.0 (1)°, respectively. An intra-molecular Se-H⋯O hydrogen bond occurs. In the crystal, mol-ecules are connected by C-H⋯O hydrogen bonds and weak C-H⋯π inter-actions help to consolidate the crystal packing.

Related literature

For industrial applications of selenium, see: Stevenson (2011 ▶); Comasseto et al. (1997 ▶). For its biological function, see: Gladyshev et al. (1996 ▶); Epp et al. (1983 ▶); Wessjohann et al. (2007 ▶).

Experimental

Crystal data

C21H18O2SSe

M = 413.37

Monoclinic,

a = 21.601 (3) Å

b = 8.5238 (12) Å

c = 21.187 (3) Å

β = 106.175 (4)°

V = 3746.5 (9) Å3

Z = 8

Mo Kα radiation

μ = 2.13 mm−1

T = 293 K

0.32 × 0.20 × 0.16 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer

20922 measured reflections

4449 independent reflections

3330 reflections with I > 2σ(I)

R int = 0.029

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.114

S = 1.01

4449 reflections

226 parameters

H-atom parameters constrained

Δρmax = 0.65 e Å−3

Δρmin = −0.28 e Å−3

Data collection: SMART (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812001638/bq2332sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812001638/bq2332Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812001638/bq2332Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C21H18O2SSe	F(000) = 1680
Mr = 413.37	Dx = 1.466 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 4449 reflections
a = 21.601 (3) Å	θ = 2.0–28.4°
b = 8.5238 (12) Å	µ = 2.13 mm−1
c = 21.187 (3) Å	T = 293 K
β = 106.175 (4)°	Needle, colorless
V = 3746.5 (9) Å3	0.32 × 0.20 × 0.16 mm
Z = 8

Bruker SMART APEX CCD area-detector diffractometer	3330 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.029
graphite	θmax = 28.4°, θmin = 2.0°
ω scans	h = −28→27
20922 measured reflections	k = −11→11
4449 independent reflections	l = −26→28

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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.114	H-atom parameters constrained
S = 1.01	w = 1/[σ2(Fo2) + (0.0722P)2 + 0.6895P] where P = (Fo2 + 2Fc2)/3
4449 reflections	(Δ/σ)max < 0.001
226 parameters	Δρmax = 0.65 e Å−3
0 restraints	Δρmin = −0.28 e Å−3

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
Se1	0.158447 (15)	0.71437 (4)	0.075900 (13)	0.06873 (13)
H1A	0.1621	0.6889	0.1141	0.103*
S1	0.12700 (3)	0.35507 (8)	0.12702 (3)	0.05289 (17)
O1	0.10403 (10)	0.1978 (3)	0.12827 (9)	0.0747 (6)
O2	0.09829 (8)	0.4776 (3)	0.15593 (8)	0.0696 (5)
C1	0.11840 (10)	0.3982 (3)	0.04198 (10)	0.0450 (5)
C2	0.09960 (12)	0.2622 (3)	−0.00303 (11)	0.0492 (5)
C3	0.03661 (15)	0.2087 (3)	−0.02158 (14)	0.0642 (7)
H3	0.0058	0.2576	−0.0053	0.077*
C4	0.0192 (2)	0.0830 (4)	−0.06412 (15)	0.0872 (11)
H4	−0.0233	0.0486	−0.0771	0.105*
C5	0.0654 (3)	0.0093 (4)	−0.08708 (17)	0.1021 (13)
H5	0.0541	−0.0761	−0.1153	0.123*
C6	0.1279 (2)	0.0611 (4)	−0.06857 (18)	0.0959 (12)
H6	0.1590	0.0110	−0.0842	0.115*
C7	0.14454 (17)	0.1860 (3)	−0.02735 (15)	0.0698 (7)
H7	0.1870	0.2207	−0.0153	0.084*
C8	0.12986 (10)	0.5387 (3)	0.01975 (10)	0.0450 (5)
C9	0.12153 (10)	0.5774 (3)	−0.05031 (10)	0.0438 (5)
C10	0.06198 (11)	0.5576 (3)	−0.09579 (11)	0.0503 (5)
H10	0.0274	0.5190	−0.0824	0.060*
C11	0.05388 (12)	0.5951 (3)	−0.16109 (11)	0.0587 (6)
H11	0.0139	0.5809	−0.1914	0.070*
C12	0.10403 (14)	0.6527 (3)	−0.18150 (12)	0.0622 (6)
H12	0.0981	0.6783	−0.2255	0.075*
C13	0.16341 (14)	0.6730 (3)	−0.13693 (13)	0.0619 (6)
H13	0.1976	0.7119	−0.1509	0.074*
C14	0.17247 (11)	0.6355 (3)	−0.07140 (12)	0.0533 (6)
H14	0.2127	0.6493	−0.0415	0.064*
C15	0.21090 (10)	0.3538 (3)	0.16456 (10)	0.0463 (5)
C16	0.23804 (12)	0.4644 (3)	0.21091 (12)	0.0612 (6)
H16	0.2128	0.5427	0.2217	0.073*
C17	0.30360 (13)	0.4579 (4)	0.24136 (13)	0.0683 (7)
H17	0.3221	0.5317	0.2734	0.082*
C18	0.34198 (12)	0.3450 (4)	0.22527 (12)	0.0597 (6)
C19	0.31359 (14)	0.2362 (3)	0.17798 (15)	0.0641 (7)
H19	0.3391	0.1599	0.1662	0.077*
C20	0.24825 (13)	0.2378 (3)	0.14778 (13)	0.0561 (6)
H20	0.2296	0.1622	0.1166	0.067*
C21	0.41369 (15)	0.3404 (5)	0.25779 (18)	0.0914 (10)
H21A	0.4324	0.2544	0.2404	0.137*
H21B	0.4214	0.3270	0.3043	0.137*
H21C	0.4328	0.4370	0.2494	0.137*

	U11	U22	U33	U12	U13	U23
Se1	0.0826 (2)	0.0716 (2)	0.04728 (17)	−0.02695 (14)	0.01026 (14)	−0.01444 (11)
S1	0.0415 (3)	0.0792 (4)	0.0358 (3)	−0.0115 (3)	0.0071 (2)	0.0064 (3)
O1	0.0680 (12)	0.0960 (16)	0.0515 (10)	−0.0343 (10)	0.0026 (9)	0.0196 (9)
O2	0.0500 (9)	0.1144 (16)	0.0488 (9)	0.0079 (10)	0.0210 (8)	0.0008 (10)
C1	0.0353 (10)	0.0628 (13)	0.0346 (10)	−0.0058 (9)	0.0061 (8)	0.0020 (9)
C2	0.0570 (13)	0.0507 (12)	0.0383 (11)	−0.0034 (10)	0.0107 (10)	0.0070 (9)
C3	0.0683 (16)	0.0668 (17)	0.0528 (15)	−0.0167 (13)	0.0087 (13)	−0.0056 (12)
C4	0.117 (3)	0.074 (2)	0.0586 (17)	−0.041 (2)	0.0050 (18)	−0.0043 (15)
C5	0.194 (5)	0.0526 (17)	0.0610 (18)	−0.025 (2)	0.037 (2)	−0.0074 (14)
C6	0.159 (4)	0.061 (2)	0.083 (2)	0.014 (2)	0.060 (3)	0.0005 (17)
C7	0.0821 (19)	0.0677 (18)	0.0652 (17)	0.0075 (14)	0.0297 (15)	0.0082 (13)
C8	0.0368 (10)	0.0551 (13)	0.0391 (10)	−0.0070 (9)	0.0040 (8)	−0.0043 (9)
C9	0.0458 (11)	0.0452 (11)	0.0380 (10)	−0.0038 (9)	0.0079 (9)	−0.0012 (9)
C10	0.0426 (11)	0.0632 (14)	0.0420 (11)	−0.0011 (10)	0.0067 (9)	0.0020 (10)
C11	0.0521 (13)	0.0794 (17)	0.0389 (12)	0.0064 (12)	0.0032 (10)	−0.0006 (11)
C12	0.0751 (17)	0.0743 (17)	0.0377 (12)	0.0038 (14)	0.0167 (12)	0.0014 (11)
C13	0.0653 (15)	0.0708 (16)	0.0548 (14)	−0.0113 (13)	0.0253 (12)	−0.0009 (12)
C14	0.0496 (12)	0.0612 (15)	0.0460 (12)	−0.0124 (11)	0.0082 (10)	−0.0036 (10)
C15	0.0418 (11)	0.0613 (13)	0.0324 (10)	−0.0050 (10)	0.0044 (8)	0.0025 (9)
C16	0.0545 (14)	0.0766 (17)	0.0467 (13)	0.0072 (12)	0.0045 (11)	−0.0137 (12)
C17	0.0558 (14)	0.0840 (19)	0.0525 (14)	−0.0063 (14)	−0.0059 (11)	−0.0184 (13)
C18	0.0450 (12)	0.0784 (17)	0.0503 (13)	−0.0020 (12)	0.0044 (10)	0.0105 (13)
C19	0.0594 (15)	0.0687 (16)	0.0628 (17)	0.0113 (13)	0.0143 (13)	0.0015 (13)
C20	0.0597 (15)	0.0565 (14)	0.0471 (13)	−0.0021 (11)	0.0065 (11)	−0.0025 (10)
C21	0.0499 (15)	0.124 (3)	0.089 (2)	0.0031 (17)	0.0002 (15)	0.009 (2)

Se1—C8	1.905 (2)	C10—H10	0.9300
Se1—H1A	0.8200	C11—C12	1.365 (4)
S1—O1	1.432 (2)	C11—H11	0.9300
S1—O2	1.436 (2)	C12—C13	1.375 (4)
S1—C15	1.765 (2)	C12—H12	0.9300
S1—C1	1.797 (2)	C13—C14	1.384 (4)
C1—C8	1.335 (3)	C13—H13	0.9300
C1—C2	1.484 (3)	C14—H14	0.9300
C2—C7	1.382 (4)	C15—C16	1.370 (3)
C2—C3	1.384 (4)	C15—C20	1.384 (4)
C3—C4	1.383 (4)	C16—C17	1.384 (4)
C3—H3	0.9300	C16—H16	0.9300
C4—C5	1.378 (6)	C17—C18	1.374 (4)
C4—H4	0.9300	C17—H17	0.9300
C5—C6	1.370 (6)	C18—C19	1.378 (4)
C5—H5	0.9300	C18—C21	1.510 (4)
C6—C7	1.360 (5)	C19—C20	1.378 (4)
C6—H6	0.9300	C19—H19	0.9300
C7—H7	0.9300	C20—H20	0.9300
C8—C9	1.482 (3)	C21—H21A	0.9600
C9—C10	1.386 (3)	C21—H21B	0.9600
C9—C14	1.389 (3)	C21—H21C	0.9600
C10—C11	1.383 (3)
C8—Se1—H1A	109.5	C12—C11—C10	120.6 (2)
O1—S1—O2	118.66 (13)	C12—C11—H11	119.7
O1—S1—C15	107.67 (12)	C10—C11—H11	119.7
O2—S1—C15	108.88 (11)	C11—C12—C13	119.9 (2)
O1—S1—C1	105.69 (11)	C11—C12—H12	120.1
O2—S1—C1	110.04 (11)	C13—C12—H12	120.1
C15—S1—C1	105.04 (10)	C12—C13—C14	120.3 (2)
C8—C1—C2	121.23 (19)	C12—C13—H13	119.9
C8—C1—S1	124.04 (17)	C14—C13—H13	119.9
C2—C1—S1	114.69 (16)	C13—C14—C9	120.1 (2)
C7—C2—C3	118.4 (3)	C13—C14—H14	119.9
C7—C2—C1	120.8 (2)	C9—C14—H14	119.9
C3—C2—C1	120.8 (2)	C16—C15—C20	120.8 (2)
C4—C3—C2	120.5 (3)	C16—C15—S1	119.97 (19)
C4—C3—H3	119.7	C20—C15—S1	119.19 (18)
C2—C3—H3	119.7	C15—C16—C17	119.0 (2)
C5—C4—C3	119.4 (3)	C15—C16—H16	120.5
C5—C4—H4	120.3	C17—C16—H16	120.5
C3—C4—H4	120.3	C18—C17—C16	121.5 (2)
C6—C5—C4	120.3 (3)	C18—C17—H17	119.3
C6—C5—H5	119.8	C16—C17—H17	119.3
C4—C5—H5	119.8	C17—C18—C19	118.4 (2)
C7—C6—C5	119.9 (4)	C17—C18—C21	121.2 (3)
C7—C6—H6	120.0	C19—C18—C21	120.4 (3)
C5—C6—H6	120.0	C18—C19—C20	121.4 (3)
C6—C7—C2	121.4 (3)	C18—C19—H19	119.3
C6—C7—H7	119.3	C20—C19—H19	119.3
C2—C7—H7	119.3	C19—C20—C15	118.9 (2)
C1—C8—C9	124.8 (2)	C19—C20—H20	120.6
C1—C8—Se1	122.99 (16)	C15—C20—H20	120.6
C9—C8—Se1	112.23 (16)	C18—C21—H21A	109.5
C10—C9—C14	119.0 (2)	C18—C21—H21B	109.5
C10—C9—C8	119.96 (19)	H21A—C21—H21B	109.5
C14—C9—C8	121.05 (19)	C18—C21—H21C	109.5
C11—C10—C9	120.1 (2)	H21A—C21—H21C	109.5
C11—C10—H10	119.9	H21B—C21—H21C	109.5
C9—C10—H10	119.9
O1—S1—C1—C8	174.4 (2)	Se1—C8—C9—C14	57.8 (3)
O2—S1—C1—C8	45.2 (2)	C14—C9—C10—C11	0.1 (4)
C15—S1—C1—C8	−71.9 (2)	C8—C9—C10—C11	179.3 (2)
O1—S1—C1—C2	−7.9 (2)	C9—C10—C11—C12	−0.4 (4)
O2—S1—C1—C2	−137.13 (17)	C10—C11—C12—C13	0.4 (4)
C15—S1—C1—C2	105.83 (18)	C11—C12—C13—C14	−0.2 (4)
C8—C1—C2—C7	74.7 (3)	C12—C13—C14—C9	−0.1 (4)
S1—C1—C2—C7	−103.1 (2)	C10—C9—C14—C13	0.1 (4)
C8—C1—C2—C3	−105.4 (3)	C8—C9—C14—C13	−179.1 (2)
S1—C1—C2—C3	76.9 (3)	O1—S1—C15—C16	−132.8 (2)
C7—C2—C3—C4	−0.8 (4)	O2—S1—C15—C16	−2.9 (2)
C1—C2—C3—C4	179.3 (2)	C1—S1—C15—C16	114.9 (2)
C2—C3—C4—C5	1.2 (5)	O1—S1—C15—C20	45.6 (2)
C3—C4—C5—C6	−0.8 (5)	O2—S1—C15—C20	175.43 (19)
C4—C5—C6—C7	0.0 (5)	C1—S1—C15—C20	−66.7 (2)
C5—C6—C7—C2	0.4 (5)	C20—C15—C16—C17	−0.6 (4)
C3—C2—C7—C6	0.0 (4)	S1—C15—C16—C17	177.8 (2)
C1—C2—C7—C6	179.9 (3)	C15—C16—C17—C18	1.2 (4)
C2—C1—C8—C9	4.0 (3)	C16—C17—C18—C19	−0.5 (4)
S1—C1—C8—C9	−178.47 (17)	C16—C17—C18—C21	178.8 (3)
C2—C1—C8—Se1	−176.64 (16)	C17—C18—C19—C20	−0.9 (4)
S1—C1—C8—Se1	0.9 (3)	C21—C18—C19—C20	179.8 (3)
C1—C8—C9—C10	58.1 (3)	C18—C19—C20—C15	1.5 (4)
Se1—C8—C9—C10	−121.4 (2)	C16—C15—C20—C19	−0.7 (4)
C1—C8—C9—C14	−122.7 (3)	S1—C15—C20—C19	−179.1 (2)

Cg1 is the centroid of the C9–C14 ring.

D—H···A	D—H	H···A	D···A	D—H···A
Se1—H1A···O2	0.82	2.57	3.141 (2)	128
C4—H4···O1i	0.93	2.75	3.557 (4)	145
C17—H17···O1ii	0.93	2.65	3.567 (3)	168
C5—H5···Cg1iii	0.93	2.92	3.615	132
C19—H19···Cg1iv	0.93	2.88	3.791	165

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C9–C14 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
Se1—H1A⋯O2	0.82	2.57	3.141 (2)	128
C4—H4⋯O1i	0.93	2.75	3.557 (4)	145
C17—H17⋯O1ii	0.93	2.65	3.567 (3)	168
C5—H5⋯Cg1iii	0.93	2.92	3.615	132
C19—H19⋯Cg1iv	0.93	2.88	3.791	165

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .