Crystal structure of 1,1'-[selanediyl-bis(4,1-phenyl-ene)]bis-(2-chloro-ethan-1-one).

In the title mol-ecule, C16H12Cl2O2Se, the C-Se-C angle is 100.05 (14)°, with the dihedral angle between the planes of the benzene rings being 69.92 (17)°. The average endocyclic angles (Se-Car-Car; ar = aromatic) facing the Se atom are 120.0 (3) and 119.4 (3)°. The Se atom is essentially coplanar with the benzene rings, with Se-Car-Car-Car torsion angles of -179.2 (3) and -179.7 (3)°. In the crystal, mol-ecules are linked via C-H⋯O hydrogen bonds forming chains propagating along the a-axis direction. The chains are linked via C-H⋯π inter-actions, forming a three-dimensional network.

Related literature

For a review of organoselenium chemistry, see: Procter (2001 ▸). For there uses as reagents and inter­mediates in organic synthesis, see: Zade et al. (2005 ▸). For their use as inter­mediates in the synthesis of pharmaceuticals, see: Woods et al. (1993 ▸), and fine chemicals and polymers, see: Hellberg et al. (1997 ▸). For their biological properties, see: Zhu & Jiang (2008 ▸); Anderson et al. (1996 ▸); Abdel-Hafez (2008 ▸). For details of how selenium compounds play important roles in protecting the heart, preventing cancer and cardiovascular diseases, see: Yang et al. (2005 ▸). For details of how selenium functions as an anti­oxidant in conjunction with vitamin E, see: Ellis et al. (1984 ▸). For the synthesis, see: Mechehoud et al. (2010 ▸). For related structures, see: Zuo (2013 ▸); Bouraoui et al. (2011 ▸).

Experimental

Crystal data

C16H12Cl2O2Se

M = 386.12

Triclinic

a = 7.9664 (7) Å

b = 9.2804 (10) Å

c = 10.9045 (12) Å

α = 104.612 (9)°

β = 95.886 (8)°

γ = 91.102 (8)°

V = 775.14 (14) Å3

Z = 2

Mo Kα radiation

μ = 2.77 mm−1

T = 293 K

0.13 × 0.08 × 0.04 mm

Data collection

Oxford Diffraction Xcalibur diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2013 ▸) T min = 0.519, T max = 1.000

8193 measured reflections

4862 independent reflections

2878 reflections with I > 2σ(I)

R int = 0.033

Refinement

R[F 2 > 2σ(F 2)] = 0.056

wR(F 2) = 0.134

S = 1.04

4862 reflections

190 parameters

H-atom parameters constrained

Δρmax = 0.59 e Å−3

Δρmin = −0.49 e Å−3

Data collection: Xcalibur (Oxford Diffraction, 2002 ▸); cell refinement: CrysAlis RED (Oxford Diffraction, 2002 ▸); data reduction: CrysAlis RED; program(s) used to solve structure: SIR2002 (Burla et al., 2005 ▸); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015 ▸); molecular graphics: PLATON (Spek, 2009 ▸); software used to prepare material for publication: SHELXL2014 and PLATON.

Crystal structure: contains datablock(s) Global, I. DOI: 10.1107/S2056989015019969/su5221sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015019969/su5221Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S2056989015019969/su5221Isup3.cml

Click here for additional data file.

. DOI: 10.1107/S2056989015019969/su5221fig1.tif

The mol­ecular structure of the title compound, with atom labelling. Displacement ellipsoids are drawn at the 50% probability level.

Click here for additional data file.

b . DOI: 10.1107/S2056989015019969/su5221fig2.tif

Crystal packing of the title compound, viewed along the b axis. The hydrogen bonds are shown as dashed lines (see Table 1).

CCDC reference: 1432588

Additional supporting information: crystallographic information; 3D view; checkCIF report

C16H12Cl2O2Se	Z = 2
Mr = 386.12	F(000) = 384
Triclinic, P1	Dx = 1.654 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.7107 Å
a = 7.9664 (7) Å	Cell parameters from 1842 reflections
b = 9.2804 (10) Å	θ = 3.9–27.7°
c = 10.9045 (12) Å	µ = 2.77 mm−1
α = 104.612 (9)°	T = 293 K
β = 95.886 (8)°	Needle, colourless
γ = 91.102 (8)°	0.13 × 0.08 × 0.04 mm
V = 775.14 (14) Å3

Oxford Diffraction Xcalibur diffractometer	2878 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.033
ω/2θ scans	θmax = 32.0°, θmin = 3.4°
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2013)	h = −11→11
Tmin = 0.519, Tmax = 1.000	k = −13→13
8193 measured reflections	l = −16→11
4862 independent reflections

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)] = 0.056	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.134	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.047P)2 + 0.1701P] where P = (Fo2 + 2Fc2)/3
4862 reflections	(Δ/σ)max < 0.001
190 parameters	Δρmax = 0.59 e Å−3
0 restraints	Δρmin = −0.49 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.

	x	y	z	Uiso*/Ueq
Se1	0.53262 (4)	0.10191 (4)	0.76583 (4)	0.05281 (16)
Cl1	−0.25879 (14)	−0.40473 (13)	0.99518 (12)	0.0730 (3)
Cl2	0.13155 (14)	0.78058 (13)	0.40236 (15)	0.0818 (4)
O1	−0.2370 (3)	−0.1702 (3)	0.8662 (3)	0.0610 (7)
O2	0.1088 (4)	0.4605 (3)	0.3572 (3)	0.0714 (8)
C1	0.3337 (4)	0.0067 (4)	0.8013 (3)	0.0394 (8)
C2	0.1712 (4)	0.0498 (4)	0.7722 (4)	0.0440 (8)
H21	0.1548	0.1271	0.7328	0.053*
C3	0.0353 (4)	−0.0224 (4)	0.8020 (3)	0.0423 (8)
H31	−0.0729	0.0071	0.7825	0.051*
C4	0.0557 (4)	−0.1385 (3)	0.8605 (3)	0.0362 (7)
C5	0.2200 (4)	−0.1800 (4)	0.8892 (3)	0.0392 (8)
H51	0.2365	−0.2574	0.9285	0.047*
C6	0.3576 (4)	−0.1082 (4)	0.8603 (3)	0.0406 (8)
H61	0.4661	−0.1368	0.8803	0.049*
C7	0.4308 (4)	0.2302 (4)	0.6692 (4)	0.0415 (8)
C8	0.3485 (5)	0.1721 (4)	0.5489 (4)	0.0488 (9)
H81	0.3415	0.0695	0.5139	0.059*
C9	0.2762 (5)	0.2656 (4)	0.4798 (4)	0.0470 (8)
H91	0.2200	0.2256	0.3989	0.056*
C10	0.2872 (4)	0.4188 (4)	0.5306 (3)	0.0402 (8)
C11	0.3757 (5)	0.4760 (4)	0.6494 (4)	0.0490 (9)
H111	0.3879	0.5787	0.6829	0.059*
C12	0.4456 (5)	0.3831 (4)	0.7184 (4)	0.0500 (9)
H121	0.5033	0.4232	0.7989	0.060*
C13	−0.0979 (4)	−0.2116 (4)	0.8894 (3)	0.0425 (8)
C14	−0.0706 (5)	−0.3401 (4)	0.9497 (4)	0.0514 (9)
H141	0.0117	−0.3087	1.0244	0.062*
H142	−0.0248	−0.4214	0.8898	0.062*
C15	0.1994 (4)	0.5136 (4)	0.4539 (4)	0.0465 (9)
C16	0.2244 (5)	0.6811 (4)	0.5070 (4)	0.0540 (10)
H161	0.3444	0.7076	0.5243	0.065*
H162	0.1758	0.7101	0.5872	0.065*

	U11	U22	U33	U12	U13	U23
Se1	0.03407 (19)	0.0680 (3)	0.0687 (3)	−0.00036 (16)	0.00438 (18)	0.0409 (2)
Cl1	0.0585 (6)	0.0786 (7)	0.0896 (9)	−0.0193 (5)	0.0163 (6)	0.0345 (6)
Cl2	0.0582 (6)	0.0802 (7)	0.1284 (12)	0.0049 (5)	0.0010 (7)	0.0700 (8)
O1	0.0318 (12)	0.0782 (19)	0.083 (2)	0.0059 (12)	0.0080 (13)	0.0385 (16)
O2	0.081 (2)	0.0686 (19)	0.060 (2)	0.0050 (16)	−0.0141 (17)	0.0170 (16)
C1	0.0312 (15)	0.0460 (18)	0.044 (2)	0.0008 (13)	0.0040 (15)	0.0170 (16)
C2	0.0387 (17)	0.0477 (19)	0.053 (2)	0.0035 (15)	0.0039 (16)	0.0268 (17)
C3	0.0326 (15)	0.0475 (19)	0.050 (2)	0.0065 (14)	0.0018 (15)	0.0183 (17)
C4	0.0303 (15)	0.0424 (17)	0.0371 (19)	0.0027 (13)	0.0037 (14)	0.0124 (15)
C5	0.0334 (15)	0.0426 (18)	0.048 (2)	0.0066 (13)	0.0045 (15)	0.0242 (16)
C6	0.0277 (14)	0.0510 (19)	0.048 (2)	0.0090 (14)	0.0006 (14)	0.0218 (16)
C7	0.0338 (16)	0.0500 (19)	0.046 (2)	−0.0004 (14)	0.0077 (16)	0.0214 (17)
C8	0.055 (2)	0.0373 (18)	0.054 (2)	−0.0036 (16)	0.0018 (19)	0.0130 (17)
C9	0.0465 (19)	0.050 (2)	0.043 (2)	−0.0039 (16)	−0.0016 (17)	0.0108 (17)
C10	0.0383 (17)	0.0430 (18)	0.044 (2)	−0.0007 (14)	0.0103 (16)	0.0178 (16)
C11	0.061 (2)	0.0396 (19)	0.045 (2)	−0.0020 (17)	0.0022 (19)	0.0107 (17)
C12	0.054 (2)	0.055 (2)	0.040 (2)	−0.0037 (18)	−0.0008 (18)	0.0127 (18)
C13	0.0337 (16)	0.053 (2)	0.042 (2)	−0.0001 (14)	0.0036 (15)	0.0146 (17)
C14	0.0443 (19)	0.057 (2)	0.059 (3)	−0.0034 (17)	0.0112 (19)	0.0253 (19)
C15	0.0394 (17)	0.054 (2)	0.053 (2)	0.0040 (16)	0.0098 (18)	0.0240 (19)
C16	0.047 (2)	0.049 (2)	0.077 (3)	0.0029 (16)	0.009 (2)	0.036 (2)

Se1—C7	1.919 (3)	C7—C8	1.377 (5)
Se1—C1	1.920 (3)	C7—C12	1.383 (5)
Cl1—C14	1.766 (4)	C8—C9	1.383 (5)
Cl2—C16	1.757 (4)	C8—H81	0.9300
O1—C13	1.203 (4)	C9—C10	1.387 (5)
O2—C15	1.202 (5)	C9—H91	0.9300
C1—C6	1.384 (5)	C10—C11	1.382 (5)
C1—C2	1.392 (4)	C10—C15	1.495 (5)
C2—C3	1.371 (5)	C11—C12	1.372 (5)
C2—H21	0.9300	C11—H111	0.9300
C3—C4	1.388 (5)	C12—H121	0.9300
C3—H31	0.9300	C13—C14	1.510 (5)
C4—C5	1.398 (4)	C14—H141	0.9700
C4—C13	1.487 (4)	C14—H142	0.9700
C5—C6	1.376 (4)	C15—C16	1.517 (5)
C5—H51	0.9300	C16—H161	0.9700
C6—H61	0.9300	C16—H162	0.9700
C7—Se1—C1	100.05 (14)	C11—C10—C9	118.8 (3)
C6—C1—C2	120.0 (3)	C11—C10—C15	123.3 (3)
C6—C1—Se1	117.0 (2)	C9—C10—C15	117.9 (3)
C2—C1—Se1	123.0 (3)	C12—C11—C10	120.8 (3)
C3—C2—C1	119.7 (3)	C12—C11—H111	119.6
C3—C2—H21	120.2	C10—C11—H111	119.6
C1—C2—H21	120.2	C11—C12—C7	120.4 (4)
C2—C3—C4	121.5 (3)	C11—C12—H121	119.8
C2—C3—H31	119.2	C7—C12—H121	119.8
C4—C3—H31	119.2	O1—C13—C4	121.8 (3)
C3—C4—C5	118.0 (3)	O1—C13—C14	121.6 (3)
C3—C4—C13	118.3 (3)	C4—C13—C14	116.7 (3)
C5—C4—C13	123.7 (3)	C13—C14—Cl1	112.6 (3)
C6—C5—C4	121.1 (3)	C13—C14—H141	109.1
C6—C5—H51	119.4	Cl1—C14—H141	109.1
C4—C5—H51	119.4	C13—C14—H142	109.1
C5—C6—C1	119.7 (3)	Cl1—C14—H142	109.1
C5—C6—H61	120.1	H141—C14—H142	107.8
C1—C6—H61	120.1	O2—C15—C10	121.9 (3)
C8—C7—C12	119.4 (3)	O2—C15—C16	121.3 (4)
C8—C7—Se1	120.7 (3)	C10—C15—C16	116.7 (3)
C12—C7—Se1	119.9 (3)	C15—C16—Cl2	112.6 (3)
C7—C8—C9	120.2 (3)	C15—C16—H161	109.1
C7—C8—H81	119.9	Cl2—C16—H161	109.1
C9—C8—H81	119.9	C15—C16—H162	109.1
C8—C9—C10	120.4 (4)	Cl2—C16—H162	109.1
C8—C9—H91	119.8	H161—C16—H162	107.8
C10—C9—H91	119.8
C6—C1—C2—C3	−0.2 (5)	C15—C10—C11—C12	176.3 (3)
Se1—C1—C2—C3	−179.2 (3)	C10—C11—C12—C7	1.0 (6)
C1—C2—C3—C4	−0.1 (6)	C8—C7—C12—C11	1.5 (5)
C2—C3—C4—C5	0.3 (5)	Se1—C7—C12—C11	179.0 (3)
C2—C3—C4—C13	−179.8 (3)	C3—C4—C13—O1	−1.9 (5)
C3—C4—C5—C6	0.0 (5)	C5—C4—C13—O1	178.0 (4)
C13—C4—C5—C6	−180.0 (3)	C3—C4—C13—C14	178.4 (3)
C4—C5—C6—C1	−0.3 (5)	C5—C4—C13—C14	−1.7 (5)
C2—C1—C6—C5	0.4 (5)	O1—C13—C14—Cl1	−6.1 (5)
Se1—C1—C6—C5	179.4 (3)	C4—C13—C14—Cl1	173.6 (3)
C12—C7—C8—C9	−2.2 (5)	C11—C10—C15—O2	−172.1 (4)
Se1—C7—C8—C9	−179.7 (3)	C9—C10—C15—O2	6.9 (5)
C7—C8—C9—C10	0.5 (5)	C11—C10—C15—C16	5.5 (5)
C8—C9—C10—C11	1.9 (5)	C9—C10—C15—C16	−175.5 (3)
C8—C9—C10—C15	−177.1 (3)	O2—C15—C16—Cl2	−7.9 (5)
C9—C10—C11—C12	−2.7 (5)	C10—C15—C16—Cl2	174.6 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C6—H61···O1i	0.93	2.41	3.288 (4)	158
C16—H161···Cg2ii	0.97	2.82	3.611 (4)	140
C16—H162···Cg1iii	0.97	2.92	3.749 (4)	144

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of benzene rings C1–C6 and C7–C12, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H61⋯O1i	0.93	2.41	3.288 (4)	158
C16—H161⋯Cg2ii	0.97	2.82	3.611 (4)	140
C16—H162⋯Cg1iii	0.97	2.92	3.749 (4)	144

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