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

In the title compound, C12H8N2O4Se, the Se atom is situated on a twofold rotational axis, so the asymmetric unit contains one half-mol-ecule. In the mol-ecule, the C-Se-C angle is 99.48 (13)°, the two benzene rings are inclined to each other at an angle of 63.8 (1)° and the nitro group is twisted by 15.9 (1)° from the attached benzene ring. In the crystal, mol-ecules are held together through weak C-H⋯O inter-actions, forming a three-dimensional network.

Related literature

For applications of organoselenium compounds, see: Mugesh et al. (2001 ▶); Nogueira et al. (2004 ▶); Wirth (1999 ▶). For details of the synthesis, see: Taniguchi (2005 ▶). The crystal structures of the related compounds bis­(p-tol­yl) selenide and bis­(4-acetyl­phen­yl) selenide were reported by Blackmore & Abrahams (1955 ▶) and Bouraoui et al. (2011 ▶), respectively.

Experimental

Crystal data

C12H8N2O4Se

M = 323.16

Monoclinic,

a = 7.207 (4) Å

b = 14.176 (7) Å

c = 11.686 (5) Å

β = 101.870 (7)°

V = 1168.3 (9) Å3

Z = 4

Mo Kα radiation

μ = 3.23 mm−1

T = 153 K

0.47 × 0.34 × 0.34 mm

Data collection

Rigaku AFC10/Saturn724+ diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku, 2008 ▶) T min = 0.314, T max = 0.402

4848 measured reflections

1557 independent reflections

1298 reflections with I > 2σ(I)

R int = 0.036

Refinement

R[F 2 > 2σ(F 2)] = 0.030

wR(F 2) = 0.074

S = 1.00

1557 reflections

87 parameters

H-atom parameters constrained

Δρmax = 0.70 e Å−3

Δρmin = −0.50 e Å−3

Data collection: CrystalClear (Rigaku, 2008 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; 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: SHELXTL.

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813007526/cv5389sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813007526/cv5389Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813007526/cv5389Isup3.cml

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

C12H8N2O4Se	F(000) = 640
Mr = 323.16	Dx = 1.837 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 1957 reflections
a = 7.207 (4) Å	θ = 2.9–29.1°
b = 14.176 (7) Å	µ = 3.23 mm−1
c = 11.686 (5) Å	T = 153 K
β = 101.870 (7)°	Block, yellow
V = 1168.3 (9) Å3	0.47 × 0.34 × 0.34 mm
Z = 4

Rigaku AFC10/Saturn724+ diffractometer	1557 independent reflections
Radiation source: fine-focus sealed tube	1298 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.036
Detector resolution: 28.5714 pixels mm-1	θmax = 29.1°, θmin = 3.2°
phi and ω scans	h = −9→9
Absorption correction: multi-scan (CrystalClear; Rigaku, 2008)	k = −19→16
Tmin = 0.314, Tmax = 0.402	l = −15→11
4848 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)] = 0.030	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.074	H-atom parameters constrained
S = 1.00	w = 1/[σ2(Fo2) + (0.0351P)2 + 0.160P] where P = (Fo2 + 2Fc2)/3
1557 reflections	(Δ/σ)max < 0.001
87 parameters	Δρmax = 0.70 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
Se	0.0000	0.05282 (2)	0.7500	0.02293 (12)
O1	−0.6302 (3)	−0.18522 (11)	0.34112 (15)	0.0281 (4)
O2	−0.5748 (2)	−0.29360 (11)	0.47417 (15)	0.0251 (4)
N1	−0.5486 (3)	−0.21464 (13)	0.43644 (16)	0.0182 (4)
C1	−0.1638 (3)	−0.03449 (14)	0.65264 (19)	0.0162 (4)
C2	−0.2197 (3)	−0.01493 (15)	0.53474 (19)	0.0166 (4)
H2	−0.1711	0.0392	0.5030	0.020*
C3	−0.3464 (3)	−0.07375 (15)	0.4622 (2)	0.0176 (5)
H3	−0.3873	−0.0601	0.3813	0.021*
C4	−0.4114 (3)	−0.15292 (14)	0.51142 (19)	0.0157 (4)
C5	−0.3547 (3)	−0.17464 (16)	0.6281 (2)	0.0195 (5)
H5	−0.3994	−0.2303	0.6588	0.023*
C6	−0.2320 (3)	−0.11472 (15)	0.70005 (19)	0.0198 (5)
H6	−0.1942	−0.1279	0.7812	0.024*

	U11	U22	U33	U12	U13	U23
Se	0.02479 (19)	0.01636 (18)	0.0236 (2)	0.000	−0.00441 (13)	0.000
O1	0.0308 (10)	0.0249 (9)	0.0228 (9)	0.0009 (7)	−0.0082 (7)	−0.0017 (7)
O2	0.0284 (10)	0.0164 (8)	0.0296 (10)	−0.0054 (7)	0.0037 (8)	−0.0012 (7)
N1	0.0158 (10)	0.0187 (10)	0.0197 (10)	0.0021 (7)	0.0024 (8)	−0.0048 (7)
C1	0.0145 (10)	0.0153 (11)	0.0180 (11)	0.0013 (8)	0.0016 (8)	−0.0020 (8)
C2	0.0163 (10)	0.0147 (10)	0.0191 (12)	0.0014 (8)	0.0039 (9)	0.0038 (8)
C3	0.0174 (11)	0.0205 (12)	0.0142 (11)	0.0038 (8)	0.0016 (8)	0.0019 (8)
C4	0.0130 (10)	0.0154 (11)	0.0182 (11)	0.0023 (8)	0.0016 (8)	−0.0045 (8)
C5	0.0223 (12)	0.0160 (11)	0.0199 (12)	−0.0010 (9)	0.0038 (9)	0.0031 (8)
C6	0.0245 (12)	0.0205 (12)	0.0134 (11)	−0.0014 (9)	0.0018 (9)	0.0026 (8)

Se—C1	1.915 (2)	C2—H2	0.9500
Se—C1i	1.915 (2)	C3—C4	1.386 (3)
O1—N1	1.221 (2)	C3—H3	0.9500
O2—N1	1.232 (2)	C4—C5	1.375 (3)
N1—C4	1.468 (3)	C5—C6	1.380 (3)
C1—C2	1.382 (3)	C5—H5	0.9500
C1—C6	1.398 (3)	C6—H6	0.9500
C2—C3	1.389 (3)
C1—Se—C1i	99.48 (13)	C4—C3—H3	121.0
O1—N1—O2	123.79 (19)	C2—C3—H3	121.0
O1—N1—C4	118.68 (18)	C5—C4—C3	122.4 (2)
O2—N1—C4	117.53 (18)	C5—C4—N1	118.99 (19)
C2—C1—C6	120.3 (2)	C3—C4—N1	118.59 (19)
C2—C1—Se	118.71 (16)	C4—C5—C6	119.3 (2)
C6—C1—Se	120.96 (17)	C4—C5—H5	120.4
C1—C2—C3	120.6 (2)	C6—C5—H5	120.4
C1—C2—H2	119.7	C5—C6—C1	119.5 (2)
C3—C2—H2	119.7	C5—C6—H6	120.2
C4—C3—C2	117.9 (2)	C1—C6—H6	120.2
C1i—Se—C1—C2	−139.8 (2)	O2—N1—C4—C5	−15.9 (3)
C1i—Se—C1—C6	42.66 (16)	O1—N1—C4—C3	−14.9 (3)
C6—C1—C2—C3	1.0 (3)	O2—N1—C4—C3	165.32 (19)
Se—C1—C2—C3	−176.55 (16)	C3—C4—C5—C6	1.5 (3)
C1—C2—C3—C4	−1.2 (3)	N1—C4—C5—C6	−177.24 (19)
C2—C3—C4—C5	−0.1 (3)	C4—C5—C6—C1	−1.7 (3)
C2—C3—C4—N1	178.67 (18)	C2—C1—C6—C5	0.4 (3)
O1—N1—C4—C5	163.9 (2)	Se—C1—C6—C5	177.94 (17)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O2ii	0.95	2.51	3.426 (3)	162
C6—H6···O2iii	0.95	2.50	3.427 (3)	164

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯O2i	0.95	2.51	3.426 (3)	162
C6—H6⋯O2ii	0.95	2.50	3.427 (3)	164

Symmetry codes: (i) ; (ii) .