1,2-Bis(4-methyl-benz-yl)diselane.

The title mol-ecule, C(16)H(18)Se(2), features a diselenide bridge between two 4-methyl-benzyl units, in which the central C-Se-Se-C torsion angle is 88.1 (3)°, while the two Se-Se-C-C fragments assume gauche conformations, with torsion angles of -51.8 (5) and 59.1 (4)°. The dihedral angle between the benzene rings is 78.9 (2)°.

Related literature

For applications of organoselenium compounds, see: Garud et al. (2007 ▶). For the synthesis of the title compound, see: Saravanan et al. (2003 ▶); Zhou et al. (2011 ▶). For related structures, see: Hua et al. (2010 ▶); Liu et al. (2006 ▶); Zhou et al. (2011 ▶).

Experimental

Crystal data

C16H18Se2

M = 368.22

Monoclinic,

a = 5.8748 (7) Å

b = 11.5315 (11) Å

c = 22.794 (3) Å

β = 91.701 (9)°

V = 1543.5 (3) Å3

Z = 4

Mo Kα radiation

μ = 4.77 mm−1

T = 293 K

0.40 × 0.09 × 0.09 mm

Data collection

Agilent Xcalibur Sapphire3 Gemini Ultra diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010 ▶) T min = 0.469, T max = 1.000

4989 measured reflections

2708 independent reflections

1806 reflections with I > 2σ(I)

R int = 0.041

Refinement

R[F 2 > 2σ(F 2)] = 0.051

wR(F 2) = 0.111

S = 1.02

2708 reflections

165 parameters

H-atom parameters constrained

Δρmax = 0.39 e Å−3

Δρmin = −0.91 e Å−3

Data collection: CrysAlis PRO (Agilent, 2010 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812007726/bh2412sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812007726/bh2412Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812007726/bh2412Isup3.cml

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

C16H18Se2	F(000) = 728
Mr = 368.22	Dx = 1.585 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.7107 Å
Hall symbol: -P 2ybc	Cell parameters from 933 reflections
a = 5.8748 (7) Å	θ = 3.2–29.4°
b = 11.5315 (11) Å	µ = 4.77 mm−1
c = 22.794 (3) Å	T = 293 K
β = 91.701 (9)°	Prism, yellow
V = 1543.5 (3) Å3	0.40 × 0.09 × 0.09 mm
Z = 4

Agilent Xcalibur Sapphire3 Gemini Ultra diffractometer	2708 independent reflections
Radiation source: Enhance (Mo) X-ray Source	1806 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.041
Detector resolution: 16.0288 pixels mm-1	θmax = 25.0°, θmin = 3.2°
ω scans	h = −4→6
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	k = −7→13
Tmin = 0.469, Tmax = 1.000	l = −27→26
4989 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)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.111	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.04P)2] where P = (Fo2 + 2Fc2)/3
2708 reflections	(Δ/σ)max = 0.001
165 parameters	Δρmax = 0.39 e Å−3
0 restraints	Δρmin = −0.91 e Å−3
0 constraints

	x	y	z	Uiso*/Ueq
Se1	0.12002 (10)	0.36751 (6)	0.23758 (3)	0.0552 (2)
Se2	0.50760 (10)	0.39377 (5)	0.24250 (3)	0.0556 (2)
C10	0.4109 (9)	0.5942 (5)	0.1691 (3)	0.0429 (14)
C6	0.5077 (10)	0.1399 (6)	0.0874 (3)	0.0559 (17)
H6	0.6441	0.1495	0.0683	0.067*
C2	0.1859 (9)	0.2269 (5)	0.1334 (2)	0.0403 (14)
C7	0.3887 (9)	0.2363 (5)	0.1049 (2)	0.0476 (15)
H7	0.4468	0.3096	0.0973	0.057*
C3	0.1048 (9)	0.1154 (5)	0.1433 (3)	0.0500 (16)
H3	−0.0323	0.1057	0.1620	0.060*
C15	0.2026 (9)	0.6475 (5)	0.1722 (3)	0.0479 (15)
H15	0.1437	0.6645	0.2087	0.057*
C1	0.0609 (9)	0.3312 (5)	0.1532 (3)	0.0514 (16)
H1A	−0.1012	0.3190	0.1465	0.062*
H1B	0.1051	0.3973	0.1298	0.062*
C9	0.5378 (10)	0.5602 (5)	0.2243 (3)	0.0638 (19)
H9A	0.4812	0.6053	0.2567	0.077*
H9B	0.6977	0.5787	0.2204	0.077*
C13	0.1619 (11)	0.6539 (5)	0.0667 (3)	0.0590 (18)
C5	0.4281 (10)	0.0295 (5)	0.0978 (3)	0.0505 (16)
C14	0.0798 (9)	0.6759 (5)	0.1216 (3)	0.0528 (17)
H14	−0.0619	0.7109	0.1246	0.063*
C11	0.4962 (10)	0.5722 (5)	0.1137 (3)	0.0530 (17)
H11	0.6380	0.5373	0.1106	0.064*
C4	0.2230 (10)	0.0197 (5)	0.1258 (3)	0.0552 (17)
H4	0.1642	−0.0536	0.1330	0.066*
C12	0.3736 (12)	0.6015 (5)	0.0636 (3)	0.0617 (18)
H12	0.4334	0.5860	0.0271	0.074*
C8	0.5624 (11)	−0.0765 (6)	0.0797 (3)	0.084 (2)
H8A	0.4714	−0.1225	0.0529	0.126*
H8B	0.6022	−0.1217	0.1139	0.126*
H8C	0.6986	−0.0523	0.0610	0.126*
C16	0.0258 (13)	0.6855 (7)	0.0112 (3)	0.106 (3)
H16A	−0.1074	0.6374	0.0079	0.159*
H16B	0.1179	0.6735	−0.0223	0.159*
H16C	−0.0191	0.7654	0.0130	0.159*

	U11	U22	U33	U12	U13	U23
Se1	0.0591 (4)	0.0521 (4)	0.0554 (4)	−0.0040 (3)	0.0163 (3)	−0.0017 (3)
Se2	0.0581 (4)	0.0471 (4)	0.0609 (5)	0.0025 (3)	−0.0119 (3)	0.0037 (4)
C10	0.038 (3)	0.028 (3)	0.063 (4)	−0.004 (3)	−0.003 (3)	−0.001 (3)
C6	0.051 (4)	0.067 (4)	0.049 (4)	−0.005 (4)	0.004 (3)	−0.005 (4)
C2	0.041 (3)	0.037 (3)	0.042 (4)	−0.005 (3)	−0.012 (3)	0.005 (3)
C7	0.054 (4)	0.039 (3)	0.049 (4)	−0.005 (3)	0.002 (3)	0.000 (3)
C3	0.041 (3)	0.058 (4)	0.051 (4)	−0.006 (3)	−0.003 (3)	0.000 (3)
C15	0.057 (4)	0.036 (3)	0.052 (4)	0.001 (3)	0.010 (3)	−0.004 (3)
C1	0.047 (3)	0.047 (4)	0.060 (4)	0.003 (3)	−0.006 (3)	−0.002 (3)
C9	0.063 (4)	0.042 (4)	0.086 (5)	−0.010 (3)	−0.009 (4)	−0.004 (4)
C13	0.063 (4)	0.045 (4)	0.069 (5)	−0.016 (4)	−0.008 (4)	0.013 (4)
C5	0.060 (4)	0.046 (4)	0.044 (4)	0.003 (3)	−0.004 (3)	−0.009 (3)
C14	0.044 (3)	0.040 (4)	0.075 (5)	0.003 (3)	0.007 (3)	0.011 (4)
C11	0.051 (4)	0.035 (4)	0.074 (5)	0.001 (3)	0.015 (3)	0.002 (4)
C4	0.063 (4)	0.044 (4)	0.058 (5)	−0.010 (3)	−0.007 (3)	0.002 (4)
C12	0.082 (5)	0.046 (4)	0.058 (5)	−0.009 (4)	0.023 (4)	0.000 (4)
C8	0.098 (6)	0.061 (5)	0.092 (6)	0.010 (4)	0.001 (4)	−0.021 (5)
C16	0.113 (6)	0.127 (7)	0.077 (6)	−0.014 (6)	−0.031 (5)	0.034 (6)

Se1—Se2	2.2964 (9)	C9—H9A	0.9700
Se1—C1	1.989 (6)	C9—H9B	0.9700
Se2—C9	1.973 (6)	C13—C14	1.377 (9)
C10—C15	1.373 (7)	C13—C12	1.386 (9)
C10—C9	1.496 (8)	C13—C16	1.521 (8)
C10—C11	1.396 (8)	C5—C4	1.385 (8)
C6—H6	0.9300	C5—C8	1.519 (8)
C6—C7	1.379 (7)	C14—H14	0.9300
C6—C5	1.379 (8)	C11—H11	0.9300
C2—C7	1.378 (7)	C11—C12	1.373 (8)
C2—C3	1.392 (7)	C4—H4	0.9300
C2—C1	1.487 (7)	C12—H12	0.9300
C7—H7	0.9300	C8—H8A	0.9600
C3—H3	0.9300	C8—H8B	0.9600
C3—C4	1.369 (8)	C8—H8C	0.9600
C15—H15	0.9300	C16—H16A	0.9600
C15—C14	1.383 (8)	C16—H16B	0.9600
C1—H1A	0.9700	C16—H16C	0.9600
C1—H1B	0.9700
C1—Se1—Se2	102.67 (16)	H9A—C9—H9B	107.8
C9—Se2—Se1	102.31 (17)	C14—C13—C12	117.7 (6)
C15—C10—C9	119.7 (6)	C14—C13—C16	121.4 (6)
C15—C10—C11	118.2 (5)	C12—C13—C16	120.9 (7)
C11—C10—C9	122.0 (5)	C6—C5—C4	117.3 (6)
C7—C6—H6	119.4	C6—C5—C8	121.0 (6)
C7—C6—C5	121.1 (6)	C4—C5—C8	121.7 (6)
C5—C6—H6	119.4	C15—C14—H14	119.1
C7—C2—C3	117.0 (5)	C13—C14—C15	121.8 (6)
C7—C2—C1	121.4 (5)	C13—C14—H14	119.1
C3—C2—C1	121.6 (5)	C10—C11—H11	119.6
C6—C7—H7	119.1	C12—C11—C10	120.9 (6)
C2—C7—C6	121.7 (5)	C12—C11—H11	119.6
C2—C7—H7	119.1	C3—C4—C5	121.6 (6)
C2—C3—H3	119.4	C3—C4—H4	119.2
C4—C3—C2	121.2 (5)	C5—C4—H4	119.2
C4—C3—H3	119.4	C13—C12—H12	119.5
C10—C15—H15	119.8	C11—C12—C13	121.0 (6)
C10—C15—C14	120.4 (6)	C11—C12—H12	119.5
C14—C15—H15	119.8	C5—C8—H8A	109.5
Se1—C1—H1A	109.0	C5—C8—H8B	109.5
Se1—C1—H1B	109.0	C5—C8—H8C	109.5
C2—C1—Se1	112.9 (4)	H8A—C8—H8B	109.5
C2—C1—H1A	109.0	H8A—C8—H8C	109.5
C2—C1—H1B	109.0	H8B—C8—H8C	109.5
H1A—C1—H1B	107.8	C13—C16—H16A	109.5
Se2—C9—H9A	109.0	C13—C16—H16B	109.5
Se2—C9—H9B	109.0	C13—C16—H16C	109.5
C10—C9—Se2	112.7 (4)	H16A—C16—H16B	109.5
C10—C9—H9A	109.0	H16A—C16—H16C	109.5
C10—C9—H9B	109.0	H16B—C16—H16C	109.5
Se1—Se2—C9—C10	−51.8 (5)	C1—Se1—Se2—C9	88.1 (3)
Se2—Se1—C1—C2	59.1 (4)	C1—C2—C7—C6	178.8 (5)
C10—C15—C14—C13	−1.0 (9)	C1—C2—C3—C4	−178.8 (5)
C10—C11—C12—C13	0.1 (9)	C9—C10—C15—C14	−177.8 (5)
C6—C5—C4—C3	−0.8 (9)	C9—C10—C11—C12	178.2 (5)
C2—C3—C4—C5	0.1 (9)	C5—C6—C7—C2	0.0 (9)
C7—C6—C5—C4	0.7 (9)	C14—C13—C12—C11	0.4 (9)
C7—C6—C5—C8	−178.5 (5)	C11—C10—C15—C14	1.4 (8)
C7—C2—C3—C4	0.6 (8)	C11—C10—C9—Se2	−78.6 (6)
C7—C2—C1—Se1	−97.9 (6)	C12—C13—C14—C15	0.1 (9)
C3—C2—C7—C6	−0.7 (8)	C8—C5—C4—C3	178.5 (6)
C3—C2—C1—Se1	81.6 (6)	C16—C13—C14—C15	−180.0 (6)
C15—C10—C9—Se2	100.6 (6)	C16—C13—C12—C11	−179.6 (6)
C15—C10—C11—C12	−0.9 (9)