Bis(4-acetyl-phen-yl) selenide.

In the title compound, C(16)H(14)O(2)Se, the dihedral angle between the benzene rings is 87.08 (11)°. In the crystal, mol-ecules are linked into layers parallel to the bc plane by inter-molecular 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 = 317.23

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.112

S = 1.04

3272 reflections

174 parameters

H-atom parameters constrained

Δρmax = 0.48 e Å−3

Δρmin = −0.59 e Å−3

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 ▶).

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

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

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

C16H14O2Se	F(000) = 640
Mr = 317.23	Dx = 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

Nonius KappaCCD diffractometer	Rint = 0.027
graphite	θmax = 27.5°, θmin = 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 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(Fo2) + (0.0407P)2 + 0.5483P] where P = (Fo2 + 2Fc2)/3
3272 reflections	(Δ/σ)max < 0.001
174 parameters	Δρmax = 0.48 e Å−3
0 restraints	Δρmin = −0.58 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
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)

	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)

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)

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

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) ; (ii) .