Bis(2,6-dichloro-benz-yl)selane.

The title mol-ecule, C(14)H(10)Cl(4)Se, features a selenide bridge between two dichloro-benzyl units. The dihedral angle between the two benzene rings is 107.9 (16)°. In the crystal, weak π-π face-to-face aromatic inter-actions are observed [centroid-centroid distance between two adjacent (but crystallographically different) phenyl rings = 3.885 (5) Å], providing some packing stability. Short Cl⋯Cl contacts of 3.41 (2) Å are observed.

Related literature

For applications of organoselenium compounds, see: Dinesh et al. (2007 ▶). For related structures, see: Fabiano et al. (2005 ▶); Fuller et al. (2010 ▶).

Experimental

Crystal data

C14H10Cl4Se

M = 398.98

Monoclinic,

a = 8.1144 (5) Å

b = 12.2250 (5) Å

c = 15.3505 (9) Å

β = 102.479 (6)°

V = 1486.78 (14) Å3

Z = 4

Mo Kα radiation

μ = 3.23 mm−1

T = 293 K

0.1 × 0.1 × 0.04 mm

Data collection

Agilent Xcalibur Sapphire3 Gemini ultra diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010 ▶) T min = 0.659, T max = 1.000

5405 measured reflections

2628 independent reflections

1902 reflections with I > 2σ(I)

R int = 0.031

Refinement

R[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.127

S = 1.04

2628 reflections

172 parameters

H-atom parameters constrained

Δρmax = 1.19 e Å−3

Δρmin = −0.50 e Å−3

Data collection: CrysAlis PRO (Agilent, 2010 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812008318/nk2146sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812008318/nk2146Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812008318/nk2146Isup3.cml

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

C14H10Cl4Se	F(000) = 784
Mr = 398.98	Dx = 1.782 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.7107 Å
a = 8.1144 (5) Å	Cell parameters from 1490 reflections
b = 12.2250 (5) Å	θ = 3.1–29.2°
c = 15.3505 (9) Å	µ = 3.23 mm−1
β = 102.479 (6)°	T = 293 K
V = 1486.78 (14) Å3	Plate, metallic pale yellow
Z = 4	0.1 × 0.1 × 0.04 mm

Agilent Xcalibur Sapphire3 Gemini ultra diffractometer	2628 independent reflections
Radiation source: Enhance (Mo) X-ray Source	1902 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.031
Detector resolution: 16.0288 pixels mm-1	θmax = 25.0°, θmin = 3.1°
ω scans	h = −9→9
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	k = −11→14
Tmin = 0.659, Tmax = 1.000	l = −10→18
5405 measured 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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.127	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.060P)2] where P = (Fo2 + 2Fc2)/3
2628 reflections	(Δ/σ)max < 0.001
172 parameters	Δρmax = 1.19 e Å−3
0 restraints	Δρmin = −0.50 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	0.89325 (7)	0.75838 (4)	0.18239 (3)	0.0556 (2)
Cl3	0.52156 (18)	0.76390 (11)	−0.06014 (11)	0.0679 (4)
Cl4	0.8752 (2)	1.05598 (11)	0.17334 (10)	0.0772 (5)
Cl2	0.66481 (17)	0.48664 (13)	0.09733 (12)	0.0758 (5)
Cl1	1.29563 (18)	0.64440 (12)	0.12621 (12)	0.0768 (5)
C9	0.7067 (6)	0.9115 (3)	0.0528 (3)	0.0394 (11)
C3	1.1568 (6)	0.5365 (4)	0.1322 (3)	0.0440 (11)
C2	0.9848 (6)	0.5574 (3)	0.1111 (3)	0.0379 (10)
C1	0.9110 (6)	0.6662 (3)	0.0799 (3)	0.0445 (12)
H1A	0.7999	0.6561	0.0419	0.053*
H1B	0.9818	0.7021	0.0452	0.053*
C14	0.7921 (7)	1.0097 (4)	0.0657 (3)	0.0487 (12)
C8	0.6873 (6)	0.8404 (4)	0.1287 (3)	0.0494 (12)
H8A	0.5964	0.7888	0.1079	0.059*
H8B	0.6552	0.8855	0.1743	0.059*
C7	0.8824 (6)	0.4681 (4)	0.1202 (3)	0.0433 (11)
C6	0.9468 (7)	0.3671 (4)	0.1470 (3)	0.0539 (14)
H6	0.8745	0.3094	0.1519	0.065*
C10	0.6395 (6)	0.8837 (4)	−0.0359 (3)	0.0432 (11)
C5	1.1186 (8)	0.3511 (4)	0.1669 (4)	0.0593 (15)
H5	1.1627	0.2824	0.1846	0.071*
C11	0.6591 (7)	0.9485 (5)	−0.1069 (4)	0.0605 (14)
H11	0.6120	0.9276	−0.1652	0.073*
C13	0.8124 (8)	1.0760 (4)	−0.0042 (4)	0.0653 (16)
H13	0.8693	1.1422	0.0071	0.078*
C12	0.7480 (8)	1.0431 (5)	−0.0901 (4)	0.0700 (17)
H12	0.7654	1.0860	−0.1373	0.084*
C4	1.2247 (7)	0.4366 (4)	0.1604 (3)	0.0543 (14)
H4	1.3411	0.4269	0.1750	0.065*

	U11	U22	U33	U12	U13	U23
Se1	0.0778 (5)	0.0396 (3)	0.0418 (3)	0.0097 (2)	−0.0041 (3)	0.0019 (2)
Cl3	0.0577 (9)	0.0589 (8)	0.0758 (10)	−0.0002 (6)	−0.0104 (7)	−0.0111 (7)
Cl4	0.1139 (14)	0.0446 (8)	0.0628 (10)	0.0014 (8)	−0.0035 (9)	−0.0108 (7)
Cl2	0.0427 (8)	0.0789 (10)	0.1042 (13)	−0.0092 (7)	0.0122 (8)	−0.0189 (9)
Cl1	0.0533 (9)	0.0711 (10)	0.1094 (13)	−0.0159 (7)	0.0250 (9)	0.0003 (9)
C9	0.044 (3)	0.031 (2)	0.044 (3)	0.015 (2)	0.014 (2)	0.006 (2)
C3	0.045 (3)	0.046 (3)	0.042 (3)	−0.003 (2)	0.011 (2)	−0.004 (2)
C2	0.039 (3)	0.042 (2)	0.030 (2)	0.000 (2)	0.004 (2)	−0.004 (2)
C1	0.049 (3)	0.043 (3)	0.039 (3)	0.002 (2)	0.006 (2)	0.010 (2)
C14	0.062 (3)	0.035 (3)	0.048 (3)	0.006 (2)	0.011 (3)	−0.001 (2)
C8	0.056 (3)	0.054 (3)	0.042 (3)	0.002 (2)	0.020 (2)	0.004 (2)
C7	0.038 (3)	0.046 (3)	0.045 (3)	−0.004 (2)	0.006 (2)	−0.010 (2)
C6	0.077 (4)	0.032 (3)	0.056 (3)	−0.008 (3)	0.021 (3)	−0.005 (2)
C10	0.041 (3)	0.042 (3)	0.045 (3)	0.007 (2)	0.005 (2)	0.000 (2)
C5	0.081 (4)	0.041 (3)	0.054 (3)	0.018 (3)	0.010 (3)	0.004 (2)
C11	0.067 (4)	0.068 (4)	0.044 (3)	0.023 (3)	0.007 (3)	0.003 (3)
C13	0.089 (5)	0.039 (3)	0.071 (4)	0.003 (3)	0.023 (3)	0.015 (3)
C12	0.090 (5)	0.065 (4)	0.062 (4)	0.013 (3)	0.032 (3)	0.027 (3)
C4	0.053 (3)	0.055 (3)	0.051 (3)	0.018 (3)	0.003 (3)	−0.006 (3)

Se1—C1	1.965 (4)	C14—C13	1.382 (7)
Se1—C8	1.970 (5)	C8—H8A	0.9700
Cl3—C10	1.745 (5)	C8—H8B	0.9700
Cl4—C14	1.738 (5)	C7—C6	1.369 (7)
Cl2—C7	1.739 (5)	C6—H6	0.9300
Cl1—C3	1.749 (5)	C6—C5	1.375 (7)
C9—C14	1.379 (6)	C10—C11	1.385 (7)
C9—C8	1.490 (6)	C5—H5	0.9300
C9—C10	1.395 (6)	C5—C4	1.372 (7)
C3—C2	1.387 (6)	C11—H11	0.9300
C3—C4	1.371 (6)	C11—C12	1.359 (8)
C2—C1	1.494 (6)	C13—H13	0.9300
C2—C7	1.397 (6)	C13—C12	1.370 (8)
C1—H1A	0.9700	C12—H12	0.9300
C1—H1B	0.9700	C4—H4	0.9300
C1—Se1—C8	99.2 (2)	C2—C7—Cl2	118.5 (4)
C14—C9—C8	122.0 (4)	C6—C7—Cl2	118.9 (4)
C14—C9—C10	115.5 (4)	C6—C7—C2	122.6 (5)
C10—C9—C8	122.4 (4)	C7—C6—H6	120.1
C2—C3—Cl1	118.4 (4)	C7—C6—C5	119.8 (5)
C4—C3—Cl1	118.0 (4)	C5—C6—H6	120.1
C4—C3—C2	123.6 (5)	C9—C10—Cl3	119.6 (4)
C3—C2—C1	123.5 (4)	C11—C10—Cl3	117.6 (4)
C3—C2—C7	115.0 (4)	C11—C10—C9	122.8 (5)
C7—C2—C1	121.5 (4)	C6—C5—H5	120.1
Se1—C1—H1A	109.6	C4—C5—C6	119.9 (5)
Se1—C1—H1B	109.6	C4—C5—H5	120.1
C2—C1—Se1	110.3 (3)	C10—C11—H11	120.5
C2—C1—H1A	109.6	C12—C11—C10	119.0 (5)
C2—C1—H1B	109.6	C12—C11—H11	120.5
H1A—C1—H1B	108.1	C14—C13—H13	120.3
C9—C14—Cl4	120.0 (4)	C12—C13—C14	119.4 (5)
C9—C14—C13	122.6 (5)	C12—C13—H13	120.3
C13—C14—Cl4	117.4 (4)	C11—C12—C13	120.6 (5)
Se1—C8—H8A	108.8	C11—C12—H12	119.7
Se1—C8—H8B	108.8	C13—C12—H12	119.7
C9—C8—Se1	113.6 (3)	C3—C4—C5	119.1 (5)
C9—C8—H8A	108.8	C3—C4—H4	120.5
C9—C8—H8B	108.8	C5—C4—H4	120.5
H8A—C8—H8B	107.7