organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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ISSN: 2056-9890

Bis(4-nitro­phen­yl) selenide

aChemical Synthesis and Pollution Control Key Laboratory of Sichuan Province, China West Normal University, Nanchong 637002, People's Republic of China
*Correspondence e-mail: zuozongle1@163.com

(Received 1 March 2013; accepted 19 March 2013; online 5 April 2013)

In the title compound, C12H8N2O4Se, the Se atom is situated on a twofold rotational axis, so the asymmetric unit contains one half-mol­ecule. In the mol­ecule, 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, mol­ecules are held together through weak C—H⋯O inter­actions, forming a three-dimensional network.

Related literature

For applications of organoselenium compounds, see: Mugesh et al. (2001[Mugesh, G., du Mont, W. W. & Sies, H. (2001). Chem. Rev. 101, 2125-2179.]); Nogueira et al. (2004[Nogueira, C. W., Zeni, G. & Rocha, J. B. (2004). Chem. Rev. 104, 6255-6285.]); Wirth (1999[Wirth, T. (1999). Tetrahedron, 55, 1-28.]). For details of the synthesis, see: Taniguchi (2005[Taniguchi, N. (2005). Synlett, pp. 1687-1690.]). The crystal structures of the related compounds bis­(p-tol­yl) selenide and bis­(4-acetyl­phen­yl) selenide were reported by Blackmore & Abrahams (1955[Blackmore, W. R. & Abrahams, S. C. (1955). Acta Cryst. 8, 323-328.]) and Bouraoui et al. (2011[Bouraoui, H., Boudjada, A., Bouacida, S., Mechehoud, Y. & Meinnel, J. (2011). Acta Cryst. E67, o941.]), respectively.

[Scheme 1]

Experimental

Crystal data
  • C12H8N2O4Se

  • Mr = 323.16

  • Monoclinic, C 2/c

  • 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[Rigaku (2008). CrystalClear. Rigaku Corporation, Tokyo, Japan.]) Tmin = 0.314, Tmax = 0.402

  • 4848 measured reflections

  • 1557 independent reflections

  • 1298 reflections with I > 2σ(I)

  • Rint = 0.036

Refinement
  • R[F2 > 2σ(F2)] = 0.030

  • wR(F2) = 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

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA 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) [x+{\script{1\over 2}}, y+{\script{1\over 2}}, z]; (ii) [x+{\script{1\over 2}}, -y-{\script{1\over 2}}, z+{\script{1\over 2}}].

Data collection: CrystalClear (Rigaku, 2008[Rigaku (2008). CrystalClear. Rigaku Corporation, Tokyo, Japan.]); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.

Supporting information


Comment top

During the past decade, organoselenium compounds have emerged their potential as drug candidates (Nogueira et al., 2004; Mugesh et al., 2001). Organoselenium compounds also exert catalytic role in organic synthesis (Wirth, 1999). Herewith we report the crystal structure of the title compound, (I).

In (I) (Fig. 1), each Se atom is situated on a twofold rotational axis, so asymmetric part contains a half of the molecule. The C—Se—C angle is 99.48 (13)°, that is similar to 99.58 (13)° observed in bis(4-acetylphenyl) selenide (Bouraoui et al., 2011), but different from 106.2 (1)° found in bis(p-tolyl) selenide (Blackmore & Abrahams, 1955). Two benzene rings in (I) are inclined to each other at 63.8 (1)° and each nitro group is twisted at 15.9 (1)° from the attached benzene ring. The crystal packing is stabilized by the weak C—H···O hydrogen bonds (Table 1).

Related literature top

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 top

The title compound has been synthesized following the procedure proposed by Taniguchi (2005). 1-Iodo-4-nitrobenzene (1.0 mmol), selenium (1.2 mmol), cuprous oxide (0.1 mmol), aluminium (2 mmol), magnesium chloride (0.5 mmol), acetylacetone (0.3 mmol), TBAF (0.2 mmol) and DMF/water (3:1, 1.0 ml) were put into a Teflon septum screw-capped tube and then sealed in the air. The reaction mixture was stirred at 120 °C for 36 h, then cooled to room temperature. Subsequently, the resulting mixture was diluted with ethyl acetate and water, and the combined organic extracts were dried with sodium sulfate anhydrous. After the solvent being removed under reduced pressure, the residue was purified by silica-gel column chromatography to afford the corresponding product. Yellow single crystals suitable for X-ray diffraction were obtained by recrystallization from acetone.

Refinement top

H atoms were placed in calculated positions, with C—H = 0.95 Å, and refined using a riding model, with Uiso(H) = 1.2Ueq(C).

Computing details top

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

Figures top
[Figure 1] Fig. 1. The molecular structure of (I) showing 50% probability displacement ellipsoids and the atomic numbering [symmetry code: (A) -x, y, 3/2-z].
Bis(4-nitrophenyl) selenide top
Crystal data top
C12H8N2O4SeF(000) = 640
Mr = 323.16Dx = 1.837 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 1957 reflections
a = 7.207 (4) Åθ = 2.9–29.1°
b = 14.176 (7) ŵ = 3.23 mm1
c = 11.686 (5) ÅT = 153 K
β = 101.870 (7)°Block, yellow
V = 1168.3 (9) Å30.47 × 0.34 × 0.34 mm
Z = 4
Data collection top
Rigaku AFC10/Saturn724+
diffractometer
1557 independent reflections
Radiation source: fine-focus sealed tube1298 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.036
Detector resolution: 28.5714 pixels mm-1θmax = 29.1°, θmin = 3.2°
phi and ω scansh = 99
Absorption correction: multi-scan
(CrystalClear; Rigaku, 2008)
k = 1916
Tmin = 0.314, Tmax = 0.402l = 1511
4848 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.030Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.074H-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 parametersΔρmax = 0.70 e Å3
0 restraintsΔρmin = 0.50 e Å3
Crystal data top
C12H8N2O4SeV = 1168.3 (9) Å3
Mr = 323.16Z = 4
Monoclinic, C2/cMo Kα radiation
a = 7.207 (4) ŵ = 3.23 mm1
b = 14.176 (7) ÅT = 153 K
c = 11.686 (5) Å0.47 × 0.34 × 0.34 mm
β = 101.870 (7)°
Data collection top
Rigaku AFC10/Saturn724+
diffractometer
1557 independent reflections
Absorption correction: multi-scan
(CrystalClear; Rigaku, 2008)
1298 reflections with I > 2σ(I)
Tmin = 0.314, Tmax = 0.402Rint = 0.036
4848 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0300 restraints
wR(F2) = 0.074H-atom parameters constrained
S = 1.00Δρmax = 0.70 e Å3
1557 reflectionsΔρmin = 0.50 e Å3
87 parameters
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Se0.00000.05282 (2)0.75000.02293 (12)
O10.6302 (3)0.18522 (11)0.34112 (15)0.0281 (4)
O20.5748 (2)0.29360 (11)0.47417 (15)0.0251 (4)
N10.5486 (3)0.21464 (13)0.43644 (16)0.0182 (4)
C10.1638 (3)0.03449 (14)0.65264 (19)0.0162 (4)
C20.2197 (3)0.01493 (15)0.53474 (19)0.0166 (4)
H20.17110.03920.50300.020*
C30.3464 (3)0.07375 (15)0.4622 (2)0.0176 (5)
H30.38730.06010.38130.021*
C40.4114 (3)0.15292 (14)0.51142 (19)0.0157 (4)
C50.3547 (3)0.17464 (16)0.6281 (2)0.0195 (5)
H50.39940.23030.65880.023*
C60.2320 (3)0.11472 (15)0.70005 (19)0.0198 (5)
H60.19420.12790.78120.024*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Se0.02479 (19)0.01636 (18)0.0236 (2)0.0000.00441 (13)0.000
O10.0308 (10)0.0249 (9)0.0228 (9)0.0009 (7)0.0082 (7)0.0017 (7)
O20.0284 (10)0.0164 (8)0.0296 (10)0.0054 (7)0.0037 (8)0.0012 (7)
N10.0158 (10)0.0187 (10)0.0197 (10)0.0021 (7)0.0024 (8)0.0048 (7)
C10.0145 (10)0.0153 (11)0.0180 (11)0.0013 (8)0.0016 (8)0.0020 (8)
C20.0163 (10)0.0147 (10)0.0191 (12)0.0014 (8)0.0039 (9)0.0038 (8)
C30.0174 (11)0.0205 (12)0.0142 (11)0.0038 (8)0.0016 (8)0.0019 (8)
C40.0130 (10)0.0154 (11)0.0182 (11)0.0023 (8)0.0016 (8)0.0045 (8)
C50.0223 (12)0.0160 (11)0.0199 (12)0.0010 (9)0.0038 (9)0.0031 (8)
C60.0245 (12)0.0205 (12)0.0134 (11)0.0014 (9)0.0018 (9)0.0026 (8)
Geometric parameters (Å, º) top
Se—C11.915 (2)C2—H20.9500
Se—C1i1.915 (2)C3—C41.386 (3)
O1—N11.221 (2)C3—H30.9500
O2—N11.232 (2)C4—C51.375 (3)
N1—C41.468 (3)C5—C61.380 (3)
C1—C21.382 (3)C5—H50.9500
C1—C61.398 (3)C6—H60.9500
C2—C31.389 (3)
C1—Se—C1i99.48 (13)C4—C3—H3121.0
O1—N1—O2123.79 (19)C2—C3—H3121.0
O1—N1—C4118.68 (18)C5—C4—C3122.4 (2)
O2—N1—C4117.53 (18)C5—C4—N1118.99 (19)
C2—C1—C6120.3 (2)C3—C4—N1118.59 (19)
C2—C1—Se118.71 (16)C4—C5—C6119.3 (2)
C6—C1—Se120.96 (17)C4—C5—H5120.4
C1—C2—C3120.6 (2)C6—C5—H5120.4
C1—C2—H2119.7C5—C6—C1119.5 (2)
C3—C2—H2119.7C5—C6—H6120.2
C4—C3—C2117.9 (2)C1—C6—H6120.2
C1i—Se—C1—C2139.8 (2)O2—N1—C4—C515.9 (3)
C1i—Se—C1—C642.66 (16)O1—N1—C4—C314.9 (3)
C6—C1—C2—C31.0 (3)O2—N1—C4—C3165.32 (19)
Se—C1—C2—C3176.55 (16)C3—C4—C5—C61.5 (3)
C1—C2—C3—C41.2 (3)N1—C4—C5—C6177.24 (19)
C2—C3—C4—C50.1 (3)C4—C5—C6—C11.7 (3)
C2—C3—C4—N1178.67 (18)C2—C1—C6—C50.4 (3)
O1—N1—C4—C5163.9 (2)Se—C1—C6—C5177.94 (17)
Symmetry code: (i) x, y, z+3/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C2—H2···O2ii0.952.513.426 (3)162
C6—H6···O2iii0.952.503.427 (3)164
Symmetry codes: (ii) x+1/2, y+1/2, z; (iii) x+1/2, y1/2, z+1/2.

Experimental details

Crystal data
Chemical formulaC12H8N2O4Se
Mr323.16
Crystal system, space groupMonoclinic, C2/c
Temperature (K)153
a, b, c (Å)7.207 (4), 14.176 (7), 11.686 (5)
β (°) 101.870 (7)
V3)1168.3 (9)
Z4
Radiation typeMo Kα
µ (mm1)3.23
Crystal size (mm)0.47 × 0.34 × 0.34
Data collection
DiffractometerRigaku AFC10/Saturn724+
diffractometer
Absorption correctionMulti-scan
(CrystalClear; Rigaku, 2008)
Tmin, Tmax0.314, 0.402
No. of measured, independent and
observed [I > 2σ(I)] reflections
4848, 1557, 1298
Rint0.036
(sin θ/λ)max1)0.684
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.030, 0.074, 1.00
No. of reflections1557
No. of parameters87
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.70, 0.50

Computer programs: CrystalClear (Rigaku, 2008), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C2—H2···O2i0.952.513.426 (3)161.6
C6—H6···O2ii0.952.503.427 (3)164.1
Symmetry codes: (i) x+1/2, y+1/2, z; (ii) x+1/2, y1/2, z+1/2.
 

References

First citationBlackmore, W. R. & Abrahams, S. C. (1955). Acta Cryst. 8, 323–328.  CSD CrossRef CAS IUCr Journals Web of Science
First citationBouraoui, H., Boudjada, A., Bouacida, S., Mechehoud, Y. & Meinnel, J. (2011). Acta Cryst. E67, o941.  Web of Science CSD CrossRef IUCr Journals
First citationMugesh, G., du Mont, W. W. & Sies, H. (2001). Chem. Rev. 101, 2125–2179.  Web of Science CrossRef PubMed CAS
First citationNogueira, C. W., Zeni, G. & Rocha, J. B. (2004). Chem. Rev. 104, 6255–6285.  Web of Science CrossRef PubMed CAS
First citationRigaku (2008). CrystalClear. Rigaku Corporation, Tokyo, Japan.
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals
First citationTaniguchi, N. (2005). Synlett, pp. 1687–1690.  Web of Science CrossRef
First citationWirth, T. (1999). Tetrahedron, 55, 1–28.  Web of Science CrossRef CAS

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