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ISSN: 2056-9890
Volume 66| Part 5| May 2010| Page o1216

2,2′-(Diselane-1,2-di­yl)dinicotinamide N,N′-di­methyl­formamide disolvate

aSchool of Chemistry and Chemical Engineering, Shanxi University, Shanxi Province, People's Republic of China
*Correspondence e-mail: xhwei@sxu.edu.cn

(Received 23 March 2010; accepted 24 April 2010; online 30 April 2010)

The asymmetric unit of the title compound, C12H10N4O2Se2·2C3H7NO, contains two solvent mol­ecules and two half mol­ecules of the dinicotinamide, each of which sits on a center of symmetry passing through the middle of the Se—Se bond. In each mol­ecule, the two pyridyl groups and diseleno group are approximately coplanar (r.m.s. deviations from planarity for all non-H atoms = 0.011 and 0.008 Å in the two mol­ecules). Inter­molecular N—H⋯O hydrogen bonds stablilize the crystal packing.

Related literature

For the potential applications of organoselenium compounds in organic synthesis, as precursors for semiconducting materials and in ligand chemistry and biochemistry, see: Mugesh et al. (2001[Mugesh, G., Mont, W.-W. & Sies, H. (2001). Chem. Rev. 101, 2125-2179.]). For related diselenide compounds, see: Bhasin & Singh (2002[Bhasin, K. K. & Singh, J. (2002). J. Organomet. Chem. 658, 71-76.]); Kienitz et al. (1996[Kienitz, C. O., Tho1ne, C., and Jones. P. G. (1996). Inorg. Chem. 35, 3990-3997.]).

[Scheme 1]

Experimental

Crystal data
  • C12H10N4O2Se2·2C3H7NO

  • Mr = 546.34

  • Triclinic, [P \overline 1]

  • a = 7.6101 (17) Å

  • b = 12.318 (3) Å

  • c = 13.420 (3) Å

  • α = 114.175 (2)°

  • β = 91.017 (3)°

  • γ = 95.833 (3)°

  • V = 1139.3 (4) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 3.28 mm−1

  • T = 298 K

  • 0.30 × 0.20 × 0.20 mm

Data collection
  • Siemens SMART CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.439, Tmax = 0.560

  • 3937 measured reflections

  • 3937 independent reflections

  • 3359 reflections with I > 2σ(I)

Refinement
  • R[F2 > 2σ(F2)] = 0.036

  • wR(F2) = 0.097

  • S = 1.03

  • 3937 reflections

  • 275 parameters

  • H-atom parameters constrained

  • Δρmax = 0.38 e Å−3

  • Δρmin = −0.73 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
N1—H1A⋯O4 0.86 2.09 2.946 (4) 170
N1—H1B⋯O3 0.86 2.03 2.869 (5) 163
N3—H3B⋯O4 0.86 2.10 2.919 (4) 158
N3—H3A⋯O1i 0.86 2.31 3.081 (4) 150
Symmetry code: (i) -x, -y+1, -z+1.

Data collection: SMART (Siemens, 1996[Siemens (1996). SMART and SAINT. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Siemens, 1996[Siemens (1996). SMART and SAINT. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; 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: SHELXL97.

Supporting information


Comment top

Organoselenium compounds have attracted much atention because of their potential applications in organic synthesis, precursors for semiconducting materials, ligand chemistry and biochemistry (Mugesh et al., 2001). During the past decade, many organoselenium compounds have been synthesized and well characterized. In contrast to alkyl, aryl, and mixed alkylaryl senium compounds, the pyridyl selenium compounds are still rare.

The unit cell contains two nicotinamide molecules and four of the solvent molecules. The asymmetric unit contains two solvent molecules and two half molecues of the nicotinamide each of which sits on a center of symmetry passing through the middle of the Se—Se bond (Fig. 1). In (I),the two independent nicotinamides (molecule A containing Se1 and molecule B containing Se2) have comparable conformations. In each nicotinamide, the two pyridyl groups and the diseleno group are approximately coplanar (r.m.s. deviations from planarity for all non-H atoms are 0.011 and 0.008Å for molecules A and B, respectively while the two CONH2 groups are rotated out of this plane by 11.0 (5)° and 18.6 (5)° for molecules A and B, respectively. Fig. 2 shows the sheets of molecules formed by intermolecular N-H···O hydrogen-bond interactions between the nicotinamides and neighbouring solvents with distances between 2.869 (5) and 3.081 (4) Å (Table 1).

The structure of (I) is similar to that of other diselenide compounds (Kienitz, et al. 1996; Bhasin and Singh 2002).The two neighbouring pyridyl groups can be brought into register by rotation about the Se—Se bond. The commonly observed approximate coplanarity of the rings and the Se—Se bonds (C—C—Se—Se or N—C—Se—Se torsion angles ca. 0°) in these molecules has been explained in terms of a minimization of Se···Se lone pair repulsion.

Related literature top

For the potential applications of organoselenium compounds in organic synthesis, as precursors for semiconducting materials and in ligand chemistry and biochemistry, see: Mugesh et al. (2001). For related diselenide compounds, see: Bhasin & Singh (2002); Kienitz et al. (1996).

Experimental top

To a vigorously stirred solution of selenium powder (1.19 g, 15 mmol) and absolute ethanol (30 ml), sodium borohydride (0.40 g, 10.6 mmol) was added at 0 °C. The mixture was warmed to room temperature and stirred for 2 h. 2-Chloro-nicotinamide (1.56 g, 10 mmol) was added and stirred for 7 days. O2 was passed through the solution slowly for 2 h after the reaction mixture was acidfied by glacial acetic. The solvents were removed in vacuo and the residue was extracted with hot dimethyl sulphoxide (DMSO) and filtered. The filtrate was poured into water( 200 ml, cooled to 0 °C). The precipitate was separated by filtration and recrystallized from DMSO-CH3OH(1:2) to give the product as yellow crystals, yield: 1.56 g, 78%; m.p. 124-125 °C. 1H-NMR ( 300 MHz, DCCl3) δ (ppm): 7.27 (d, 2H), 7.81 (s, 2H), 8.14 (d, 2H), 8.32 (s, 2H), 8.48 (s, 2H), 8.65 (s, 2H);77Se-NMR (57 MHz, DMSO-d6 ) δ(ppm): 524.77.

Refinement top

(type here to add refinement details)

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT (Siemens, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXL97 (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. Structure showing 50 % probability.
2,2'-(Diselane-1,2-diyl)dinicotinamide N,N'-dimethylformamide disolvate top
Crystal data top
C12H10N4O2Se2·2C3H7NOZ = 2
Mr = 546.34F(000) = 548
Triclinic, P1Dx = 1.593 Mg m3
a = 7.6101 (17) ÅMo Kα radiation, λ = 0.71073 Å
b = 12.318 (3) ÅCell parameters from 2815 reflections
c = 13.420 (3) Åθ = 3.1–27.5°
α = 114.175 (2)°µ = 3.28 mm1
β = 91.017 (3)°T = 298 K
γ = 95.833 (3)°Block, yellow
V = 1139.3 (4) Å30.30 × 0.20 × 0.20 mm
Data collection top
Siemens SMART CCD
diffractometer
3937 independent reflections
Radiation source: fine-focus sealed tube3359 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.000
phi and ω scansθmax = 25.0°, θmin = 1.7°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 98
Tmin = 0.439, Tmax = 0.560k = 1413
3937 measured reflectionsl = 015
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)] = 0.036Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.097H-atom parameters constrained
S = 1.03 w = 1/[σ2(Fo2) + (0.0416P)2 + 0.7097P]
where P = (Fo2 + 2Fc2)/3
3937 reflections(Δ/σ)max = 0.001
275 parametersΔρmax = 0.38 e Å3
0 restraintsΔρmin = 0.73 e Å3
Crystal data top
C12H10N4O2Se2·2C3H7NOγ = 95.833 (3)°
Mr = 546.34V = 1139.3 (4) Å3
Triclinic, P1Z = 2
a = 7.6101 (17) ÅMo Kα radiation
b = 12.318 (3) ŵ = 3.28 mm1
c = 13.420 (3) ÅT = 298 K
α = 114.175 (2)°0.30 × 0.20 × 0.20 mm
β = 91.017 (3)°
Data collection top
Siemens SMART CCD
diffractometer
3937 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
3359 reflections with I > 2σ(I)
Tmin = 0.439, Tmax = 0.560Rint = 0.000
3937 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0360 restraints
wR(F2) = 0.097H-atom parameters constrained
S = 1.03Δρmax = 0.38 e Å3
3937 reflectionsΔρmin = 0.73 e Å3
275 parameters
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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
Se10.44747 (5)0.90079 (3)0.43528 (3)0.04343 (13)
Se20.00660 (5)0.90803 (3)0.92023 (2)0.04228 (13)
N10.1532 (5)0.5410 (3)0.7795 (2)0.0635 (10)
H1A0.14270.50360.70930.076*
H1B0.21260.51390.81760.076*
N20.0893 (4)0.8848 (2)1.1107 (2)0.0425 (7)
N30.2600 (5)0.5278 (3)0.3920 (3)0.0592 (9)
H3A0.21170.47940.32890.071*
H3B0.25800.50660.44570.071*
N40.5588 (4)0.9107 (3)0.6373 (2)0.0486 (7)
N50.3752 (5)0.2618 (4)0.9343 (3)0.0708 (10)
N60.0494 (5)0.2208 (3)0.4807 (2)0.0551 (8)
O10.0074 (4)0.6808 (2)0.77632 (19)0.0673 (9)
O20.3436 (5)0.6689 (2)0.3326 (2)0.0745 (9)
O30.3116 (6)0.4039 (4)0.8778 (3)0.1119 (15)
O40.1655 (4)0.4149 (2)0.5403 (2)0.0636 (8)
C10.0787 (5)0.6393 (3)0.8283 (3)0.0453 (8)
C20.0992 (4)0.7021 (3)0.9497 (2)0.0385 (7)
C30.1484 (5)0.6470 (3)1.0157 (3)0.0444 (8)
H30.16890.56710.98400.053*
C40.1672 (5)0.7094 (3)1.1279 (3)0.0501 (9)
H40.19830.67271.17280.060*
C50.1388 (5)0.8271 (3)1.1708 (3)0.0481 (9)
H50.15470.87001.24630.058*
C60.0676 (4)0.8226 (3)1.0022 (2)0.0359 (7)
C70.3379 (5)0.6354 (3)0.4068 (3)0.0485 (9)
C80.4199 (5)0.7156 (3)0.5172 (3)0.0415 (8)
C90.4458 (6)0.6768 (3)0.5990 (3)0.0555 (10)
H90.40740.59800.58690.067*
C100.5283 (6)0.7548 (4)0.6982 (3)0.0649 (12)
H100.54600.72990.75390.078*
C110.5836 (6)0.8695 (4)0.7131 (3)0.0597 (11)
H110.64170.92160.77970.072*
C120.4806 (4)0.8354 (3)0.5408 (3)0.0382 (7)
C130.4094 (8)0.1434 (5)0.9066 (7)0.132 (3)
H13A0.39840.09980.82850.198*
H13B0.32590.10590.93900.198*
H13C0.52730.14360.93340.198*
C140.3803 (8)0.3421 (6)1.0492 (5)0.1017 (18)
H14A0.35860.42031.05640.153*
H14B0.49470.34711.08330.153*
H14C0.29100.31201.08420.153*
C150.3437 (7)0.3039 (5)0.8611 (4)0.0867 (15)
H150.34630.25080.78820.104*
C160.0269 (7)0.1122 (4)0.3893 (4)0.0864 (16)
H16A0.04930.12950.32700.130*
H16B0.13610.08200.40890.130*
H16C0.05410.05300.37150.130*
C170.0853 (7)0.2161 (4)0.5860 (4)0.0791 (14)
H17A0.17660.27910.62800.119*
H17B0.12330.14000.57410.119*
H17C0.02050.22600.62520.119*
C180.0939 (6)0.3203 (4)0.4690 (3)0.0571 (10)
H180.06900.31930.40050.069*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Se10.0546 (2)0.0391 (2)0.0405 (2)0.00010 (15)0.00515 (15)0.02201 (17)
Se20.0608 (2)0.0352 (2)0.02975 (19)0.00734 (15)0.00560 (15)0.01226 (15)
N10.103 (3)0.051 (2)0.0322 (15)0.0285 (19)0.0013 (16)0.0088 (14)
N20.0567 (18)0.0399 (16)0.0296 (14)0.0083 (13)0.0010 (12)0.0127 (12)
N30.084 (2)0.0411 (18)0.0469 (17)0.0106 (16)0.0191 (16)0.0181 (15)
N40.062 (2)0.0385 (16)0.0464 (17)0.0001 (14)0.0092 (14)0.0207 (14)
N50.062 (2)0.079 (3)0.081 (3)0.0151 (19)0.0075 (19)0.041 (2)
N60.074 (2)0.0438 (18)0.0476 (18)0.0091 (15)0.0171 (16)0.0181 (15)
O10.113 (2)0.0510 (16)0.0310 (12)0.0239 (16)0.0190 (14)0.0072 (12)
O20.125 (3)0.0538 (17)0.0457 (15)0.0128 (17)0.0233 (16)0.0281 (14)
O30.153 (4)0.094 (3)0.108 (3)0.067 (3)0.014 (3)0.049 (2)
O40.097 (2)0.0467 (16)0.0417 (14)0.0024 (14)0.0025 (14)0.0150 (13)
C10.067 (2)0.0349 (18)0.0308 (16)0.0060 (16)0.0036 (16)0.0105 (14)
C20.0447 (19)0.0359 (18)0.0297 (16)0.0021 (14)0.0026 (13)0.0090 (14)
C30.057 (2)0.0401 (19)0.0380 (18)0.0119 (16)0.0013 (15)0.0168 (15)
C40.067 (2)0.053 (2)0.0384 (18)0.0134 (18)0.0000 (17)0.0252 (17)
C50.065 (2)0.050 (2)0.0280 (16)0.0102 (17)0.0010 (15)0.0142 (16)
C60.0424 (18)0.0341 (17)0.0315 (16)0.0016 (13)0.0021 (13)0.0148 (14)
C70.060 (2)0.041 (2)0.0445 (19)0.0041 (16)0.0108 (16)0.0180 (16)
C80.048 (2)0.0393 (18)0.0399 (18)0.0020 (15)0.0030 (15)0.0198 (15)
C90.080 (3)0.040 (2)0.051 (2)0.0009 (18)0.0083 (19)0.0255 (18)
C100.101 (3)0.052 (2)0.046 (2)0.004 (2)0.019 (2)0.0288 (19)
C110.081 (3)0.052 (2)0.044 (2)0.001 (2)0.0196 (19)0.0210 (19)
C120.0416 (18)0.0377 (18)0.0389 (17)0.0032 (14)0.0027 (14)0.0200 (15)
C130.086 (4)0.098 (5)0.256 (9)0.029 (3)0.059 (5)0.112 (6)
C140.077 (4)0.134 (5)0.101 (4)0.006 (3)0.000 (3)0.061 (4)
C150.088 (4)0.097 (4)0.076 (3)0.030 (3)0.008 (3)0.033 (3)
C160.102 (4)0.050 (3)0.081 (3)0.009 (2)0.031 (3)0.004 (2)
C170.089 (4)0.091 (4)0.086 (3)0.016 (3)0.012 (3)0.064 (3)
C180.080 (3)0.055 (2)0.0370 (19)0.007 (2)0.0086 (18)0.0202 (19)
Geometric parameters (Å, º) top
Se1—C121.918 (3)C3—C41.379 (5)
Se1—Se1i2.3889 (8)C3—H30.9300
Se2—C61.919 (3)C4—C51.365 (5)
Se2—Se2ii2.3877 (7)C4—H40.9300
N1—C11.312 (4)C5—H50.9300
N1—H1A0.8600C7—C81.484 (5)
N1—H1B0.8600C8—C91.383 (5)
N2—C61.336 (4)C8—C121.403 (5)
N2—C51.346 (4)C9—C101.375 (5)
N3—C71.330 (5)C9—H90.9300
N3—H3A0.8600C10—C111.363 (5)
N3—H3B0.8600C10—H100.9300
N4—C111.328 (5)C11—H110.9300
N4—C121.330 (4)C13—H13A0.9600
N5—C151.313 (6)C13—H13B0.9600
N5—C131.403 (6)C13—H13C0.9600
N5—C141.449 (7)C14—H14A0.9600
N6—C181.311 (5)C14—H14B0.9600
N6—C161.451 (5)C14—H14C0.9600
N6—C171.460 (5)C15—H150.9300
O1—C11.233 (4)C16—H16A0.9600
O2—C71.224 (4)C16—H16B0.9600
O3—C151.210 (6)C16—H16C0.9600
O4—C181.229 (5)C17—H17A0.9600
C1—C21.487 (4)C17—H17B0.9600
C2—C31.385 (4)C17—H17C0.9600
C2—C61.406 (4)C18—H180.9300
C12—Se1—Se1i92.21 (10)C10—C9—H9120.1
C6—Se2—Se2ii92.67 (9)C8—C9—H9120.1
C1—N1—H1A120.0C11—C10—C9118.6 (3)
C1—N1—H1B120.0C11—C10—H10120.7
H1A—N1—H1B120.0C9—C10—H10120.7
C6—N2—C5117.6 (3)N4—C11—C10123.3 (4)
C7—N3—H3A120.0N4—C11—H11118.3
C7—N3—H3B120.0C10—C11—H11118.3
H3A—N3—H3B120.0N4—C12—C8122.6 (3)
C11—N4—C12118.4 (3)N4—C12—Se1116.3 (2)
C15—N5—C13123.2 (5)C8—C12—Se1121.1 (2)
C15—N5—C14118.6 (5)N5—C13—H13A109.5
C13—N5—C14118.2 (5)N5—C13—H13B109.5
C18—N6—C16121.4 (4)H13A—C13—H13B109.5
C18—N6—C17119.9 (4)N5—C13—H13C109.5
C16—N6—C17118.6 (4)H13A—C13—H13C109.5
O1—C1—N1121.8 (3)H13B—C13—H13C109.5
O1—C1—C2119.4 (3)N5—C14—H14A109.5
N1—C1—C2118.8 (3)N5—C14—H14B109.5
C3—C2—C6117.2 (3)H14A—C14—H14B109.5
C3—C2—C1122.8 (3)N5—C14—H14C109.5
C6—C2—C1120.0 (3)H14A—C14—H14C109.5
C4—C3—C2120.6 (3)H14B—C14—H14C109.5
C4—C3—H3119.7O3—C15—N5127.4 (5)
C2—C3—H3119.7O3—C15—H15116.3
C5—C4—C3117.8 (3)N5—C15—H15116.3
C5—C4—H4121.1N6—C16—H16A109.5
C3—C4—H4121.1N6—C16—H16B109.5
N2—C5—C4124.0 (3)H16A—C16—H16B109.5
N2—C5—H5118.0N6—C16—H16C109.5
C4—C5—H5118.0H16A—C16—H16C109.5
N2—C6—C2122.7 (3)H16B—C16—H16C109.5
N2—C6—Se2116.1 (2)N6—C17—H17A109.5
C2—C6—Se2121.2 (2)N6—C17—H17B109.5
O2—C7—N3122.0 (3)H17A—C17—H17B109.5
O2—C7—C8120.0 (3)N6—C17—H17C109.5
N3—C7—C8118.0 (3)H17A—C17—H17C109.5
C9—C8—C12117.2 (3)H17B—C17—H17C109.5
C9—C8—C7123.0 (3)O4—C18—N6125.9 (4)
C12—C8—C7119.8 (3)O4—C18—H18117.0
C10—C9—C8119.9 (3)N6—C18—H18117.0
Symmetry codes: (i) x+1, y+2, z+1; (ii) x, y+2, z+2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···O40.862.092.946 (4)170
N1—H1B···O30.862.032.869 (5)163
N3—H3B···O40.862.102.919 (4)158
N3—H3A···O1iii0.862.313.081 (4)150
Symmetry code: (iii) x, y+1, z+1.

Experimental details

Crystal data
Chemical formulaC12H10N4O2Se2·2C3H7NO
Mr546.34
Crystal system, space groupTriclinic, P1
Temperature (K)298
a, b, c (Å)7.6101 (17), 12.318 (3), 13.420 (3)
α, β, γ (°)114.175 (2), 91.017 (3), 95.833 (3)
V3)1139.3 (4)
Z2
Radiation typeMo Kα
µ (mm1)3.28
Crystal size (mm)0.30 × 0.20 × 0.20
Data collection
DiffractometerSiemens SMART CCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.439, 0.560
No. of measured, independent and
observed [I > 2σ(I)] reflections
3937, 3937, 3359
Rint0.000
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.036, 0.097, 1.03
No. of reflections3937
No. of parameters275
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.38, 0.73

Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···O40.862.092.946 (4)170.0
N1—H1B···O30.862.032.869 (5)163.2
N3—H3B···O40.862.102.919 (4)157.9
N3—H3A···O1i0.862.313.081 (4)149.8
Symmetry code: (i) x, y+1, z+1.
 

Acknowledgements

We thank the SNSF (Nos. 2008011021 and 2008012013-2) and the Homecoming Foundation of Shanxi Province for support.

References

First citationBhasin, K. K. & Singh, J. (2002). J. Organomet. Chem. 658, 71–76.  Web of Science CSD CrossRef CAS
First citationKienitz, C. O., Tho1ne, C., and Jones. P. G. (1996). Inorg. Chem. 35, 3990–3997.
First citationMugesh, G., Mont, W.-W. & Sies, H. (2001). Chem. Rev. 101, 2125–2179.  Web of Science CrossRef PubMed CAS
First citationSheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals
First citationSiemens (1996). SMART and SAINT. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.

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Volume 66| Part 5| May 2010| Page o1216
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