Bis(4-acetyl­phen­yl) selenide

Bouraoui, H.; Boudjada, A.; Bouacida, S.; Mechehoud, Y.; Meinnel, J.

doi:10.1107/S1600536811009962

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 67| Part 4| April 2011| Page o941

doi:10.1107/S1600536811009962

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Bis(4-acetylphenyl) selenide

Hazem Bouraoui,^a Ali Boudjada,^a Sofiane Bouacida,^b ^*‡ Youcef Mechehoud ^c and Jean Meinnel ^d

^aLaboratoire de Cristallographie, Département de Physique, Université Mentouri-Constantine, 25000 Constantine, Algeria, ^bUnité de Recherche de Chimie de l'Environnement et Moléculaire Structurale, CHEMS, Université Mentouri-Constantine, 25000 Algeria, ^cLaboratoire VAREN, Département de Chimie, Faculté des Sciences Exactes, Université Mentouri-Constantine, 25000 Constantine, Algeria, and ^dUMR 6226 CNRS–Université Rennes 1 `Sciences Chimiques de Rennes', Equipe `Matière Condensée et Systèmes Electroactifs', 263 Avenue du Général Leclerc, F-35042 Rennes, France
^*Correspondence e-mail: bouacida_sofiane@yahoo.fr

(Received 4 March 2011; accepted 16 March 2011; online 23 March 2011)

In the title compound, C₁₆H₁₄O₂Se, the dihedral angle between the benzene rings is 87.08 (11)°. In the crystal, molecules are linked into layers parallel to the bc plane by intermolecular C—H⋯O hydrogen bonds.

Related literature

For the synthesis of the title compound, see: Henry (1943 ). For biological properties and applications of organoselenide compounds, see: Clement et al. (1997 ); Anderson et al. (1996 ); Abdel-Hafez (2008 ); Woods et al. (1993 ); Hellberg et al. (1997 ). For a description of the Cambridge Structural Database, see: Allen (2002 ).

Experimental

Crystal data

C₁₆H₁₄O₂Se
M_r = 317.23
Monoclinic, P 2₁ /c
a = 14.9290 (7) Å
b = 7.7223 (3) Å
c = 13.8345 (6) Å
β = 115.993 (2)°
V = 1433.60 (11) Å³
Z = 4
Mo Kα radiation
μ = 2.61 mm⁻¹
T = 295 K
0.14 × 0.07 × 0.05 mm

Data collection

Nonius KappaCCD diffractometer
6274 measured reflections
3272 independent reflections
1904 reflections with I > 2σ(I)
R_int = 0.027

Refinement

R[F² > 2σ(F²)] = 0.041
wR(F²) = 0.112
S = 1.04
3272 reflections
174 parameters
H-atom parameters constrained
Δρ_max = 0.48 e Å⁻³
Δρ_min = −0.59 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯O2ⁱ	0.93	2.47	3.272 (5)	145
C12—H12⋯O1ⁱⁱ	0.93	2.53	3.317 (4)	143
Symmetry codes: (i) $[x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ ; (ii) x, y-1, z.

Data collection: KappaCCD Reference Manual (Nonius, 1998 ); cell refinement: SCALEPACK (Otwinowski & Minor, 1997 ); data reduction: SCALEPACK and DENZO (Otwinowski & Minor, 1997); program(s) used to solve structure: SIR2002 (Burla et al., 2003 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ); molecular graphics: ORTEP-3 (Farrugia, 1997 ) and DIAMOND (Brandenburg & Berndt, 2001 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811009962/rz2569sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811009962/rz2569Isup2.hkl

checkCIF report

Comment top

Organoselenides and derivatives are of considerable interest in academia as anti-cancer (Clement et al., 1997), anti-oxydant (Anderson et al., 1996), anti-inflammatory and antiallergic agents (Abdel-Hafez, 2008), and in industry because of their wide involvement as key intermediates for the synthesis of pharmaceuticals (Woods et al., 1993), perfumes, fine chemicals and polymers (Hellberg et al., 1997). In the framework of our ongoing program related to the synthesis and pharmaceutical evaluation of new organoselenide derivatives, we report here the synthesis and crystal structure of the title compound.

In the molecule of the title compound (Fig. 1), the selenium atom is linked to two phenyl acetyl groups. All bond distances and angles are within the ranges of accepted values (CSD; Allen, 2002). The molecule is not planar, as can be seen from the dihedral angle of 87.08 (11)° between the planes of the two benzene rings. In the crystal structure, molecules are linked into chains running parallel to the c axis by intermolecular C2—H2···O2 hydrogen interactions (Fig. 2, Table 1). The chains are further connected by C12—H12···O1 hydrogen bonds to form layers parallel to the bc plane (Fig. 3).

Related literature top

For the synthesis of the title compound, see: Henry (1943). For biological properties and applications of organoselenide compounds, see: Clement et al. (1997); Anderson et al. (1996); Abdel-Hafez (2008); Woods et al. (1993); Hellberg et al. (1997). For a description of the Cambridge Structural Database, see: Allen (2002).

Experimental top

The title compound was prepared according to a literature method (Henry, 1943). Methyl acyl chloride (2.4 mmol) and anhydrous aluminium chloride (3.0 mmol) were dissolved in dry methylene chloride (4 ml). The reaction mixture was cooled at 0–5 °C, protected from atmospheric moisture, and stirred continuously from 15 min. A solution of diphenyl selenide (1 mmol) in methylene chloride (0.5 ml) was then added dropwise over a period of 5 min. The reaction mixture was allowed to reach room temperature gradually and stirred at this temperature overnight. The solution was then washed with ice water-HCl and extracted with methylene chloride. The organic layer was separated and dried over Na₂SO₄. Removal of the solvent afforded the crude title product which was recrystallized from CH₃OH. Some crystals suitable for X-ray diffraction analysis were carefully isolated under polarizing microscope.

Computing details top

Data collection: KappaCCD Reference Manual (Nonius, 1998); cell refinement: SCALEPACK (Otwinowski & Minor, 1997); data reduction: SCALEPACK and DENZO (Otwinowski & Minor, 1997); program(s) used to solve structure: SIR2002 (Burla et al., 2003); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia,1997) and DIAMOND (Brandenburg & Berndt, 2001); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top

	Fig. 1. The molecular structure of the title compound with displacement ellipsoids drawn at the 50% probability level.
	Fig. 2. Packing diagram of the title compound viewed down the b axis showing the chains parallel to the c axis formed by hydrogen bonds (dashed line).
	Fig. 3. Crystal packing of the title compound viewed down the a axis showing a layer parallel to the bc plane. Hhydrogen bonds are shown as dashed lines.

1-{4-[(4-acetylphenylidene)selanyl]phenyl}ethanone top

Crystal data top

C₁₆H₁₄O₂Se	F(000) = 640
M_r = 317.23	D_x = 1.47 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 14.9290 (7) Å	Cell parameters from 9479 reflections
b = 7.7223 (3) Å	θ = 2.9–27.5°
c = 13.8345 (6) Å	µ = 2.61 mm⁻¹
β = 115.993 (2)°	T = 295 K
V = 1433.60 (11) Å³	Needle, white
Z = 4	0.14 × 0.07 × 0.05 mm

Data collection top

Nonius KappaCCD diffractometer	R_int = 0.027
Graphite monochromator	θ_max = 27.5°, θ_min = 3.0°
CCD rotation images, thick slices scans	h = −19→19
6274 measured reflections	k = −9→10
3272 independent reflections	l = −17→17
1904 reflections with I > 2σ(I)

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.112	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0407P)² + 0.5483P] where P = (F_o² + 2F_c²)/3
3272 reflections	(Δ/σ)_max < 0.001
174 parameters	Δρ_max = 0.48 e Å⁻³
0 restraints	Δρ_min = −0.59 e Å⁻³

Crystal data top

C₁₆H₁₄O₂Se	V = 1433.60 (11) Å³
M_r = 317.23	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 14.9290 (7) Å	µ = 2.61 mm⁻¹
b = 7.7223 (3) Å	T = 295 K
c = 13.8345 (6) Å	0.14 × 0.07 × 0.05 mm
β = 115.993 (2)°

Data collection top

Nonius KappaCCD diffractometer	1904 reflections with I > 2σ(I)
6274 measured reflections	R_int = 0.027
3272 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	0 restraints
wR(F²) = 0.112	H-atom parameters constrained
S = 1.04	Δρ_max = 0.48 e Å⁻³
3272 reflections	Δρ_min = −0.59 e Å⁻³
174 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
C1	0.1305 (3)	0.6107 (4)	0.4328 (3)	0.0693 (8)
C2	0.0389 (3)	0.6402 (5)	0.3498 (3)	0.0807 (10)
H2	0.0275	0.6113	0.2801	0.097*
C3	−0.0369 (3)	0.7122 (5)	0.3678 (3)	0.0758 (9)
H3	−0.0985	0.7327	0.3101	0.091*
C4	−0.0222 (2)	0.7546 (4)	0.4719 (2)	0.0631 (8)
C5	0.0705 (3)	0.7225 (4)	0.5546 (3)	0.0699 (8)
H5	0.0820	0.7490	0.6247	0.084*
C6	0.1463 (3)	0.6524 (4)	0.5365 (3)	0.0727 (9)
H6	0.2083	0.6330	0.5939	0.087*
C7	0.2962 (2)	0.7077 (4)	0.3840 (2)	0.0610 (7)
C8	0.2529 (2)	0.8705 (4)	0.3634 (2)	0.0643 (8)
H8	0.1896	0.8864	0.3594	0.077*
C9	0.3038 (2)	1.0081 (4)	0.3489 (2)	0.0614 (7)
H9	0.2743	1.1170	0.3352	0.074*
C10	0.3987 (2)	0.9885 (4)	0.3543 (2)	0.0550 (7)
C11	0.4414 (2)	0.8249 (4)	0.3750 (2)	0.0618 (8)
H11	0.5049	0.8091	0.3793	0.074*
C12	0.3904 (2)	0.6849 (4)	0.3891 (3)	0.0683 (8)
H12	0.4194	0.5755	0.4021	0.082*
C13	−0.1026 (3)	0.8262 (4)	0.4962 (3)	0.0715 (9)
C14	0.4524 (2)	1.1412 (4)	0.3393 (2)	0.0613 (8)
C15	−0.2035 (3)	0.8594 (6)	0.4069 (3)	0.0998 (13)
H15A	−0.2445	0.9155	0.4350	0.150*
H15B	−0.2335	0.7515	0.3743	0.150*
H15C	−0.1974	0.9326	0.3540	0.150*
C16	0.5559 (2)	1.1204 (5)	0.3517 (3)	0.0722 (9)
H16A	0.5821	1.2315	0.3462	0.108*
H16B	0.5557	1.0456	0.2962	0.108*
H16C	0.5968	1.0707	0.4208	0.108*
O1	0.41088 (19)	1.2823 (3)	0.3175 (2)	0.0912 (8)
O2	−0.08802 (19)	0.8541 (4)	0.5879 (2)	0.0940 (8)
Se1	0.23415 (3)	0.50420 (5)	0.40667 (4)	0.08634 (18)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.078 (2)	0.068 (2)	0.074 (2)	−0.0169 (17)	0.0436 (19)	−0.0041 (16)
C2	0.092 (3)	0.094 (3)	0.064 (2)	−0.023 (2)	0.041 (2)	−0.0082 (18)
C3	0.070 (2)	0.095 (3)	0.0593 (19)	−0.0153 (19)	0.0254 (17)	−0.0016 (17)
C4	0.069 (2)	0.0613 (18)	0.0599 (19)	−0.0142 (15)	0.0291 (17)	0.0000 (14)
C5	0.076 (2)	0.077 (2)	0.0569 (18)	−0.0084 (18)	0.0297 (17)	−0.0080 (16)
C6	0.071 (2)	0.078 (2)	0.070 (2)	−0.0039 (17)	0.0309 (18)	−0.0003 (17)
C7	0.075 (2)	0.0568 (17)	0.0604 (17)	−0.0054 (15)	0.0377 (15)	−0.0072 (14)
C8	0.0614 (19)	0.068 (2)	0.0678 (19)	0.0008 (15)	0.0326 (16)	0.0010 (15)
C9	0.0596 (18)	0.0568 (17)	0.0649 (18)	0.0086 (15)	0.0245 (15)	0.0081 (15)
C10	0.0651 (18)	0.0518 (16)	0.0498 (15)	0.0013 (14)	0.0268 (13)	−0.0029 (13)
C11	0.070 (2)	0.0547 (17)	0.0726 (19)	0.0023 (15)	0.0428 (17)	−0.0032 (14)
C12	0.088 (2)	0.0492 (16)	0.084 (2)	0.0072 (15)	0.0521 (19)	−0.0029 (15)
C13	0.074 (2)	0.066 (2)	0.073 (2)	−0.0098 (16)	0.0311 (18)	−0.0018 (17)
C14	0.071 (2)	0.0548 (18)	0.0572 (17)	−0.0027 (15)	0.0275 (16)	0.0018 (14)
C15	0.073 (3)	0.119 (4)	0.097 (3)	0.007 (2)	0.028 (2)	−0.001 (2)
C16	0.079 (2)	0.075 (2)	0.072 (2)	−0.0066 (18)	0.0422 (18)	0.0016 (17)
O1	0.0897 (17)	0.0572 (14)	0.126 (2)	0.0055 (13)	0.0468 (16)	0.0179 (14)
O2	0.0921 (18)	0.116 (2)	0.0801 (17)	0.0134 (15)	0.0433 (14)	−0.0069 (15)
Se1	0.1093 (3)	0.0598 (2)	0.1188 (4)	−0.0126 (2)	0.0767 (3)	−0.0080 (2)

Geometric parameters (Å, º) top

C13—O2	1.209 (4)	C2—H2	0.9300
C13—C4	1.486 (4)	C3—C4	1.397 (4)
C13—C15	1.494 (5)	C3—H3	0.9300
C14—O1	1.224 (4)	C4—C5	1.378 (4)
C14—C16	1.488 (4)	C5—C6	1.373 (4)
C14—C10	1.490 (4)	C5—H5	0.9300
C15—H15A	0.9600	C6—H6	0.9300
C15—H15B	0.9600	C7—C8	1.385 (4)
C15—H15C	0.9600	C7—C12	1.389 (4)
C16—H16A	0.9600	C8—C9	1.371 (4)
C16—H16B	0.9600	C8—H8	0.9300
C16—H16C	0.9600	C9—C10	1.394 (4)
Se1—C7	1.918 (3)	C9—H9	0.9300
Se1—C1	1.921 (3)	C10—C11	1.387 (4)
C1—C2	1.366 (5)	C11—C12	1.385 (4)
C1—C6	1.386 (4)	C11—H11	0.9300
C2—C3	1.378 (5)	C12—H12	0.9300

O2—C13—C4	120.8 (3)	C5—C4—C3	117.4 (3)
O2—C13—C15	119.3 (3)	C5—C4—C13	119.7 (3)
C4—C13—C15	119.9 (3)	C3—C4—C13	122.9 (3)
O1—C14—C16	120.8 (3)	C6—C5—C4	121.9 (3)
O1—C14—C10	119.6 (3)	C6—C5—H5	119.1
C16—C14—C10	119.6 (3)	C4—C5—H5	119.1
C13—C15—H15A	109.5	C5—C6—C1	120.0 (3)
C13—C15—H15B	109.5	C5—C6—H6	120.0
H15A—C15—H15B	109.5	C1—C6—H6	120.0
C13—C15—H15C	109.5	C8—C7—C12	119.7 (3)
H15A—C15—H15C	109.5	C8—C7—Se1	124.2 (2)
H15B—C15—H15C	109.5	C12—C7—Se1	116.0 (2)
C14—C16—H16A	109.5	C9—C8—C7	119.7 (3)
C14—C16—H16B	109.5	C9—C8—H8	120.1
H16A—C16—H16B	109.5	C7—C8—H8	120.1
C14—C16—H16C	109.5	C8—C9—C10	121.5 (3)
H16A—C16—H16C	109.5	C8—C9—H9	119.2
H16B—C16—H16C	109.5	C10—C9—H9	119.2
C7—Se1—C1	99.58 (13)	C11—C10—C9	118.3 (3)
C2—C1—C6	119.0 (3)	C11—C10—C14	121.5 (3)
C2—C1—Se1	120.3 (3)	C9—C10—C14	120.2 (3)
C6—C1—Se1	120.6 (3)	C12—C11—C10	120.6 (3)
C1—C2—C3	120.9 (3)	C12—C11—H11	119.7
C1—C2—H2	119.5	C10—C11—H11	119.7
C3—C2—H2	119.5	C11—C12—C7	120.1 (3)
C2—C3—C4	120.7 (3)	C11—C12—H12	120.0
C2—C3—H3	119.6	C7—C12—H12	120.0
C4—C3—H3	119.6

C7—Se1—C1—C2	91.3 (3)	C1—Se1—C7—C8	−15.7 (3)
C7—Se1—C1—C6	−91.3 (3)	C1—Se1—C7—C12	164.3 (2)
C6—C1—C2—C3	0.7 (5)	C12—C7—C8—C9	−0.4 (5)
Se1—C1—C2—C3	178.2 (3)	Se1—C7—C8—C9	179.6 (2)
C1—C2—C3—C4	−0.9 (5)	C7—C8—C9—C10	0.0 (5)
C2—C3—C4—C5	0.3 (5)	C8—C9—C10—C11	0.0 (4)
C2—C3—C4—C13	−177.6 (3)	C8—C9—C10—C14	−179.4 (3)
O2—C13—C4—C5	−1.2 (5)	O1—C14—C10—C11	177.4 (3)
C15—C13—C4—C5	−179.3 (3)	C16—C14—C10—C11	−2.9 (4)
O2—C13—C4—C3	176.7 (3)	O1—C14—C10—C9	−3.3 (4)
C15—C13—C4—C3	−1.5 (5)	C16—C14—C10—C9	176.4 (3)
C3—C4—C5—C6	0.3 (5)	C9—C10—C11—C12	0.4 (4)
C13—C4—C5—C6	178.3 (3)	C14—C10—C11—C12	179.7 (3)
C4—C5—C6—C1	−0.5 (5)	C10—C11—C12—C7	−0.7 (5)
C2—C1—C6—C5	−0.1 (5)	C8—C7—C12—C11	0.7 (5)
Se1—C1—C6—C5	−177.5 (3)	Se1—C7—C12—C11	−179.3 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O2ⁱ	0.93	2.47	3.272 (5)	145
C12—H12···O1ⁱⁱ	0.93	2.53	3.317 (4)	143

Symmetry codes: (i) x, −y+3/2, z−1/2; (ii) x, y−1, z.

Experimental details

Crystal data
Chemical formula	C₁₆H₁₄O₂Se
M_r	317.23
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	295
a, b, c (Å)	14.9290 (7), 7.7223 (3), 13.8345 (6)
β (°)	115.993 (2)
V (Å³)	1433.60 (11)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	2.61
Crystal size (mm)	0.14 × 0.07 × 0.05

Data collection
Diffractometer	Nonius KappaCCD diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	6274, 3272, 1904
R_int	0.027
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.112, 1.04
No. of reflections	3272
No. of parameters	174
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.48, −0.59

Computer programs: KappaCCD Reference Manual (Nonius, 1998), SCALEPACK (Otwinowski & Minor, 1997), SCALEPACK and DENZO (Otwinowski & Minor, 1997), SIR2002 (Burla et al., 2003), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia,1997) and DIAMOND (Brandenburg & Berndt, 2001), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O2ⁱ	0.93	2.47	3.272 (5)	145
C12—H12···O1ⁱⁱ	0.93	2.53	3.317 (4)	143

Symmetry codes: (i) x, −y+3/2, z−1/2; (ii) x, y−1, z.

Footnotes

‡Current address: Département Sciences de la Matière, Faculté des Sciences Exactes et Sciences de la Nature et de la Vie, Université Larbi Ben M'hidi, Oum El Bouaghi 04000, Algeria.

Acknowledgements

This work was supported by the Laboratoire de Cristallographie, Département de Physique, Université Mentouri-Constantine, Algeria and UMR 6226 CNRS-Université Rennes 1 `Sciences Chimiques de Rennes', France.

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