(Z)-2-[(4-Methyl­phen­yl)sulfon­yl]-1,2-diphenyl­ethene­selenol

Natarajan, S.; Mathews, R.

doi:10.1107/S1600536812001638

organic compounds

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ISSN: 2056-9890

Volume 68| Part 2| February 2012| Page o442

doi:10.1107/S1600536812001638

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(Z)-2-[(4-Methylphenyl)sulfonyl]-1,2-diphenyletheneselenol

Sampath Natarajan ^a ^* and Rita Mathews ^a

^aDepartment of Advanced Technology Fusion, Konkuk University, 1 Hwayang-dong, Gwangjin-gu, Seoul 143 701, Republic of Korea
^*Correspondence e-mail: sams76@gmail.com

(Received 6 January 2012; accepted 13 January 2012; online 18 January 2012)

In the title compound, C₂₁H₁₈O₂SSe, 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 intramolecular Se—H⋯O hydrogen bond occurs. In the crystal, molecules are connected by C—H⋯O hydrogen bonds and weak C—H⋯π interactions 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_r = 413.37
Monoclinic, C 2/c
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[F² > 2σ(F²)] = 0.040
wR(F²) = 0.114
S = 1.01
4449 reflections
226 parameters
H-atom parameters constrained
Δρ_max = 0.65 e Å⁻³
Δρ_min = −0.28 e Å⁻³

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⋯Cg1^iv	0.93	2.88	3.791	165
Symmetry codes: (i) -x, -y, -z; (ii) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iii) x, y-1, z; (iv) $[-x+{\script{1\over 2}}, -y+{\script{1\over 2}}, -z]$ .

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 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812001638/bq2332sup1.cif

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

Supporting information file. DOI: 10.1107/S1600536812001638/bq2332Isup3.cml

checkCIF report

Comment top

Selenium is chemically related to sulfur and oxygen and has a wide range of applications in the inorganic field, including uses in semiconductors, photovoltaic and photocell devices, and photographic toner applications. It is used industrially to produce deep red color in glasses and ceramics (Stevenson, 2011). Vinylic selenides are organoselenium compounds that play a role in organic synthesis, especially in the development of convenient stereoselective routes to functionalized alkenes (Comasseto et al., 1997). Selenols have important roles in certain biological processes. Three enzymes namely iodothyronine deiodinase, glutathione peroxidase (Epp et al., 1983) and thioredoxin reductase (Gladyshev et al., 1996) found in mammals contain selenols at their active sites. The selenols in these proteins are part of the essential amino acid selenocysteine (Wessjohann et al., 2007).

The title molecule is an organoselenium compound (Fig. 1) containing three phenyl rings with vinylic selenol group. The dihedral angle between the cis substituted phenyl rings is 64.3 (1)°. The dihedral angles between the toluene sufonyl and the phenyl rings substituted on C1 and C8 atoms are 21.1 (2)° and 72.0 (1)°, respectively. The molecules are not showing any classical hydrogen bonds, still the molecules accept a Se—H···O type intra (Fig.2) and two C—H···O type intermolecular interactions. In addition, two C—H···π interactions also help to consolidate the molecules in the unit cell crystal packing. The complete details of the molecular interactions are shown in Table 1.

Related literature top

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 top

The compound 2-phenylacetophenone (0.1M) was heated with Woollins' reagent (1 equiv.) in toluene to produce 2-phenylselenoacetophenone. Then 1 equiv. of this compound was stirred with p-toluenesulfonylchloride (1 equiv.) in the presence of triethylamine (2 equiv.) in dry THF resulted the title compound and was recrystallized using methanol.

Computing details top

Data collection: SMART (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); 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).

Figures top

	Fig. 1. ORTEP diagram of the title molecule with the atom numbering scheme. Displacement ellipsoids are drawn at 30% probability level.
	Fig. 2. A unit cell packing of the crystal structure of the title compound viewed down a axis. The dashed lines indicate the hydrogen bonds.

(Z)-2-[(4-Methylphenyl)sulfonyl]-1,2-diphenyletheneselenol top

Crystal data top

C₂₁H₁₈O₂SSe	F(000) = 1680
M_r = 413.37	D_x = 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

Data collection top

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

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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.114	H-atom parameters constrained
S = 1.01	w = 1/[σ²(F_o²) + (0.0722P)² + 0.6895P] where P = (F_o² + 2F_c²)/3
4449 reflections	(Δ/σ)_max < 0.001
226 parameters	Δρ_max = 0.65 e Å⁻³
0 restraints	Δρ_min = −0.28 e Å⁻³

Crystal data top

C₂₁H₁₈O₂SSe	V = 3746.5 (9) Å³
M_r = 413.37	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 21.601 (3) Å	µ = 2.13 mm⁻¹
b = 8.5238 (12) Å	T = 293 K
c = 21.187 (3) Å	0.32 × 0.20 × 0.16 mm
β = 106.175 (4)°

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	3330 reflections with I > 2σ(I)
20922 measured reflections	R_int = 0.029
4449 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.040	0 restraints
wR(F²) = 0.114	H-atom parameters constrained
S = 1.01	Δρ_max = 0.65 e Å⁻³
4449 reflections	Δρ_min = −0.28 e Å⁻³
226 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
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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···Cg1^iv	0.93	2.88	3.791	165

Symmetry codes: (i) −x, −y, −z; (ii) −x+1/2, y+1/2, −z+1/2; (iii) x, y−1, z; (iv) −x+1/2, −y+1/2, −z.

Experimental details

Crystal data
Chemical formula	C₂₁H₁₈O₂SSe
M_r	413.37
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	293
a, b, c (Å)	21.601 (3), 8.5238 (12), 21.187 (3)
β (°)	106.175 (4)
V (Å³)	3746.5 (9)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	2.13
Crystal size (mm)	0.32 × 0.20 × 0.16

Data collection
Diffractometer	Bruker SMART APEX CCD area-detector diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	20922, 4449, 3330
R_int	0.029
(sin θ/λ)_max (Å⁻¹)	0.669

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.040, 0.114, 1.01
No. of reflections	4449
No. of parameters	226
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.65, −0.28

Computer programs: SMART (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

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···Cg1^iv	0.93	2.88	3.791	165

Symmetry codes: (i) −x, −y, −z; (ii) −x+1/2, y+1/2, −z+1/2; (iii) x, y−1, z; (iv) −x+1/2, −y+1/2, −z.

References

Bruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Comasseto, J. V., Ling, L. W., Petragnani, N. & Stefani, H. A. (1997). Synthesis, 4, 373–403. CrossRef Web of Science Google Scholar
Epp, O., Ladensteine, R. & Wendel, A. (1983). Eur. J. Biochem. 133, 51–69. CrossRef CAS PubMed Web of Science Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Gladyshev, V. N., Jeang, K. T. & Stadtman, T. C. (1996). Proc. Natl Acad. Sci. USA, 93, 6146–6151. CrossRef CAS PubMed Web of Science Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Stevenson, F. Jr (2011). Molecules, 16, 3232–3251. Web of Science PubMed Google Scholar
Wessjohann, L. A., Schneider, A. Abbas, M. & Brandt, W. (2007). Biol. Chem. 388, 997–1006. Web of Science CrossRef PubMed CAS Google Scholar

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Volume 68| Part 2| February 2012| Page o442

doi:10.1107/S1600536812001638

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