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

The title compound, C(14)H(12)N(2)O(4)Se(2), is not chiral, but the mol-ecules assume a chiral conformation in the solid state and crystallize as an aggregate. The central C-Se-Se-C torsion angle is 90.4 (2)°, while the two Se-Se-C-C fragments assume gauche conformations with values of -59.4 (5) and 67.5 (4)°. The dihedral angle between the two benzene rings is 80.74 (14)°.

Related literature

For potential applications of organoselenium compounds, see: Jung & Seo (2010 ▶). For the preparation, see: Saravanan et al. (2003 ▶). For related structures, see: Fuller et al. (2010 ▶); Lari et al. (2009 ▶); Hua et al. (2010 ▶).

Experimental

Crystal data

C14H12N2O4Se2

M = 430.18

Orthorhombic,

a = 5.88324 (14) Å

b = 14.3571 (3) Å

c = 18.3012 (4) Å

V = 1545.83 (6) Å3

Z = 4

Cu Kα radiation

μ = 6.17 mm−1

T = 296 K

0.3 × 0.09 × 0.09 mm

Data collection

Agilent Xcalibur Gemini Ultra diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010 ▶) T min = 0.546, T max = 1.000

3179 measured reflections

2098 independent reflections

2015 reflections with I > 2σ(I)

R int = 0.017

Refinement

R[F 2 > 2σ(F 2)] = 0.031

wR(F 2) = 0.101

S = 1.02

2098 reflections

199 parameters

H-atom parameters constrained

Δρmax = 0.50 e Å−3

Δρmin = −0.50 e Å−3

Absolute structure: Flack (1983 ▶), 659 Friedel pairs

Flack parameter: −0.02 (4)

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/S1600536811025736/fy2016sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811025736/fy2016Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811025736/fy2016Isup3.cml

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

C14H12N2O4Se2	Dx = 1.848 Mg m−3
Mr = 430.18	Cu Kα radiation, λ = 1.5418 Å
Orthorhombic, P212121	Cell parameters from 2222 reflections
a = 5.88324 (14) Å	θ = 3.1–62.7°
b = 14.3571 (3) Å	µ = 6.17 mm−1
c = 18.3012 (4) Å	T = 296 K
V = 1545.83 (6) Å3	Prism, metallic yellow
Z = 4	0.3 × 0.09 × 0.09 mm
F(000) = 840

Agilent Xcalibur Gemini Ultra diffractometer	2098 independent reflections
Radiation source: Enhance Ultra (Cu)	2015 reflections with I > 2σ(I)
mirror	Rint = 0.017
Detector resolution: 16.0288 pixels mm-1	θmax = 62.8°, θmin = 5.7°
ω scans	h = −6→6
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	k = −14→16
Tmin = 0.546, Tmax = 1.000	l = −20→20
3179 measured reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.031	H-atom parameters constrained
wR(F2) = 0.101	w = 1/[σ2(Fo2) + (0.080P)2] where P = (Fo2 + 2Fc2)/3
S = 1.02	(Δ/σ)max = 0.002
2098 reflections	Δρmax = 0.50 e Å−3
199 parameters	Δρmin = −0.50 e Å−3
0 restraints	Absolute structure: Flack (1983), 659 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: −0.02 (4)

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
Se2	3.00649 (10)	1.38512 (3)	1.48718 (4)	0.0630 (2)
Se1	2.62212 (11)	1.35765 (4)	1.47622 (3)	0.0608 (2)
N2	2.6203 (9)	1.7770 (3)	1.6536 (2)	0.0574 (11)
C5	2.8508 (10)	1.5182 (3)	1.2268 (2)	0.0470 (11)
C4	2.9801 (10)	1.4419 (3)	1.2412 (3)	0.0515 (12)
H4	3.1209	1.4345	1.2188	0.062*
C2	2.6858 (9)	1.3852 (3)	1.3212 (3)	0.0495 (11)
C6	2.6351 (10)	1.5309 (4)	1.2571 (3)	0.0544 (12)
H6	2.5479	1.5830	1.2459	0.065*
O3	2.7429 (9)	1.8188 (3)	1.6950 (3)	0.0934 (16)
C1	2.6009 (13)	1.3139 (4)	1.3742 (3)	0.0686 (16)
H1A	2.6891	1.2573	1.3688	0.082*
H1B	2.4437	1.2994	1.3630	0.082*
O2	2.8277 (10)	1.6613 (3)	1.1697 (3)	0.0825 (13)
C3	2.9010 (9)	1.3758 (3)	1.2891 (3)	0.0510 (11)
H3	2.9908	1.3245	1.3004	0.061*
N1	2.9363 (10)	1.5909 (4)	1.1763 (3)	0.0660 (13)
O1	3.1181 (10)	1.5750 (4)	1.1456 (3)	0.0941 (16)
C7	2.5553 (10)	1.4625 (4)	1.3047 (3)	0.0586 (13)
H7	2.4122	1.4689	1.3257	0.070*
C14	2.7061 (8)	1.6189 (3)	1.4953 (3)	0.0453 (10)
H14	2.6300	1.6012	1.4530	0.054*
C13	2.6056 (8)	1.6823 (3)	1.5430 (3)	0.0486 (11)
H13	2.4625	1.7067	1.5330	0.058*
C8	3.0283 (10)	1.5164 (3)	1.4576 (3)	0.0554 (12)
H8A	3.1874	1.5330	1.4527	0.066*
H8B	2.9576	1.5238	1.4100	0.066*
C9	2.9178 (8)	1.5818 (3)	1.5104 (3)	0.0465 (10)
O4	2.4153 (7)	1.7875 (3)	1.6518 (3)	0.0748 (11)
C11	2.9349 (8)	1.6723 (4)	1.6212 (3)	0.0501 (12)
H11	3.0131	1.6911	1.6628	0.060*
C10	3.0275 (8)	1.6080 (3)	1.5737 (3)	0.0500 (11)
H10	3.1677	1.5816	1.5847	0.060*
C12	2.7213 (8)	1.7083 (3)	1.6049 (3)	0.0444 (10)

	U11	U22	U33	U12	U13	U23
Se2	0.0811 (4)	0.0354 (3)	0.0723 (4)	0.0084 (3)	−0.0118 (3)	0.0036 (2)
Se1	0.0845 (4)	0.0429 (3)	0.0549 (3)	−0.0137 (3)	0.0117 (3)	0.0030 (2)
N2	0.078 (3)	0.039 (2)	0.055 (2)	−0.005 (2)	0.005 (2)	−0.001 (2)
C5	0.059 (3)	0.042 (2)	0.039 (2)	0.002 (2)	0.000 (2)	−0.004 (2)
C4	0.055 (3)	0.053 (3)	0.047 (2)	0.012 (3)	0.001 (2)	−0.010 (2)
C2	0.059 (3)	0.039 (2)	0.050 (2)	−0.011 (2)	−0.005 (2)	−0.008 (2)
C6	0.057 (3)	0.052 (3)	0.054 (3)	0.013 (3)	−0.007 (2)	−0.005 (2)
O3	0.096 (3)	0.078 (3)	0.107 (4)	−0.019 (3)	0.000 (3)	−0.041 (3)
C1	0.098 (4)	0.048 (3)	0.060 (3)	−0.023 (3)	−0.007 (3)	−0.011 (2)
O2	0.109 (3)	0.054 (2)	0.085 (3)	0.006 (3)	−0.011 (3)	0.021 (2)
C3	0.065 (3)	0.037 (2)	0.051 (2)	0.008 (2)	−0.004 (2)	−0.005 (2)
N1	0.084 (3)	0.058 (3)	0.055 (2)	−0.009 (3)	−0.009 (3)	0.003 (2)
O1	0.094 (3)	0.102 (4)	0.086 (3)	−0.005 (3)	0.032 (3)	0.022 (3)
C7	0.055 (3)	0.064 (3)	0.056 (3)	−0.003 (3)	−0.003 (2)	−0.005 (3)
C14	0.050 (2)	0.038 (2)	0.048 (2)	−0.003 (2)	−0.0052 (19)	0.000 (2)
C13	0.050 (2)	0.037 (2)	0.059 (3)	−0.003 (2)	−0.003 (2)	0.006 (2)
C8	0.063 (3)	0.035 (2)	0.068 (3)	−0.004 (2)	0.007 (3)	0.001 (2)
C9	0.056 (2)	0.0276 (19)	0.055 (2)	−0.006 (2)	0.005 (2)	0.0058 (19)
O4	0.067 (3)	0.077 (3)	0.080 (3)	0.017 (2)	0.006 (2)	−0.010 (2)
C11	0.056 (3)	0.049 (3)	0.046 (2)	−0.010 (2)	−0.008 (2)	0.000 (2)
C10	0.049 (2)	0.046 (2)	0.055 (3)	0.001 (2)	0.000 (2)	0.011 (2)
C12	0.055 (3)	0.031 (2)	0.047 (2)	−0.006 (2)	0.003 (2)	0.005 (2)

Se2—Se1	2.3043 (8)	O2—N1	1.201 (7)
Se2—C8	1.965 (5)	C3—H3	0.9300
Se1—C1	1.973 (5)	N1—O1	1.230 (8)
N2—O3	1.206 (6)	C7—H7	0.9300
N2—O4	1.216 (7)	C14—H14	0.9300
N2—C12	1.455 (6)	C14—C13	1.393 (7)
C5—C4	1.360 (7)	C14—C9	1.382 (7)
C5—C6	1.396 (9)	C13—H13	0.9300
C5—N1	1.482 (7)	C13—C12	1.374 (7)
C4—H4	0.9300	C8—H8A	0.9700
C4—C3	1.373 (7)	C8—H8B	0.9700
C2—C1	1.496 (8)	C8—C9	1.496 (7)
C2—C3	1.402 (8)	C9—C10	1.379 (7)
C2—C7	1.382 (7)	C11—H11	0.9300
C6—H6	0.9300	C11—C10	1.380 (7)
C6—C7	1.395 (8)	C11—C12	1.391 (7)
C1—H1A	0.9700	C10—H10	0.9300
C1—H1B	0.9700
C8—Se2—Se1	101.78 (18)	O1—N1—C5	116.7 (5)
C1—Se1—Se2	101.5 (2)	C2—C7—C6	120.9 (5)
O3—N2—O4	123.2 (6)	C2—C7—H7	119.5
O3—N2—C12	118.5 (5)	C6—C7—H7	119.5
O4—N2—C12	118.2 (5)	C13—C14—H14	119.7
C4—C5—C6	122.4 (5)	C9—C14—H14	119.7
C4—C5—N1	119.9 (5)	C9—C14—C13	120.6 (4)
C6—C5—N1	117.7 (5)	C14—C13—H13	120.5
C5—C4—H4	120.3	C12—C13—C14	118.9 (4)
C5—C4—C3	119.4 (5)	C12—C13—H13	120.5
C3—C4—H4	120.3	Se2—C8—H8A	108.9
C3—C2—C1	120.5 (5)	Se2—C8—H8B	108.9
C7—C2—C1	120.3 (5)	H8A—C8—H8B	107.7
C7—C2—C3	119.2 (5)	C9—C8—Se2	113.3 (3)
C5—C6—H6	121.2	C9—C8—H8A	108.9
C7—C6—C5	117.6 (5)	C9—C8—H8B	108.9
C7—C6—H6	121.2	C14—C9—C8	120.3 (4)
Se1—C1—H1A	109.2	C10—C9—C14	119.0 (4)
Se1—C1—H1B	109.2	C10—C9—C8	120.7 (5)
C2—C1—Se1	112.0 (3)	C10—C11—H11	121.0
C2—C1—H1A	109.2	C10—C11—C12	118.1 (4)
C2—C1—H1B	109.2	C12—C11—H11	121.0
H1A—C1—H1B	107.9	C9—C10—C11	121.8 (5)
C4—C3—C2	120.5 (5)	C9—C10—H10	119.1
C4—C3—H3	119.8	C11—C10—H10	119.1
C2—C3—H3	119.8	C13—C12—N2	119.2 (4)
O2—N1—C5	118.3 (5)	C13—C12—C11	121.5 (4)
O2—N1—O1	124.9 (6)	C11—C12—N2	119.3 (4)
Se2—Se1—C1—C2	−59.4 (5)	N1—C5—C4—C3	178.7 (4)
Se2—C8—C9—C14	−102.1 (4)	N1—C5—C6—C7	−179.8 (5)
Se2—C8—C9—C10	79.7 (5)	C7—C2—C1—Se1	−75.3 (6)
Se1—Se2—C8—C9	67.5 (4)	C7—C2—C3—C4	−0.8 (7)
C5—C4—C3—C2	2.1 (7)	C14—C13—C12—N2	177.9 (4)
C5—C6—C7—C2	0.1 (8)	C14—C13—C12—C11	−0.4 (7)
C4—C5—C6—C7	1.2 (8)	C14—C9—C10—C11	−2.1 (7)
C4—C5—N1—O2	−173.5 (5)	C13—C14—C9—C8	−177.7 (4)
C4—C5—N1—O1	4.8 (7)	C13—C14—C9—C10	0.5 (6)
C6—C5—C4—C3	−2.3 (8)	C8—Se2—Se1—C1	90.4 (2)
C6—C5—N1—O2	7.5 (7)	C8—C9—C10—C11	176.2 (4)
C6—C5—N1—O1	−174.2 (5)	C9—C14—C13—C12	0.6 (7)
O3—N2—C12—C13	−159.1 (5)	O4—N2—C12—C13	22.8 (7)
O3—N2—C12—C11	19.2 (7)	O4—N2—C12—C11	−158.9 (5)
C1—C2—C3—C4	−179.2 (5)	C10—C11—C12—N2	−179.4 (4)
C1—C2—C7—C6	178.1 (5)	C10—C11—C12—C13	−1.1 (7)
C3—C2—C1—Se1	103.0 (5)	C12—C11—C10—C9	2.3 (7)
C3—C2—C7—C6	−0.2 (8)