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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 66| Part 1| January 2010| Pages m42-m43
doi:10.1107/S1600536809052556

trans-(2,2′-Bi­pyrimidine)di­iodido(isopropoxido)oxidorhenium(V)

Andrzej Kochela*

aFaculty of Chemistry, University of Wrocław, 14 Joliot-Curie St, 50-383 Wrocław, Poland
*Correspondence e-mail: garfild9@gazeta.pl

(Received 16 November 2009; accepted 7 December 2009; online 12 December 2009)

In the title compound, [Re(C3H7O)I2O(C8H6N4)], the ReV atom adopts a distorted octa­hedral ReI2O2N2 geometry, with the O atoms in a trans conformation and the I atoms in a cis conformation. Two intra­molecular C—H⋯I contacts occur. The crystal structure is stabilized by inter­molecular C—H⋯O, C—H⋯N and C—H⋯I hydrogen bonds.

Related literature

For related structures and for further discussion of rhenium structural chemistry, see: Abrahams et al. (2005[Abrahams, A., Gerber, T. A. & Mayer, P. (2005). J. Coord. Chem. 58, 1387-1393.], 2007[Abrahams, A., Gerber, T. A., Luzipo, D. R. & Mayer, P. (2007). J. Coord. Chem. 60, 2207-2213.]); Abram et al. (1995[Abram, S., Abram, U., Schulz-Lang, E. & Strähle, J. (1995). Acta Cryst. C51, 1078-1080.]); Ciani et al. (1983[Ciani, G. F., D'Alfonso, G., Romiti, P. F., Sironi, A. & Freni, M. (1983). Inorg. Chim. Acta, 72, 29-37.]); Gerber et al. (2004[Gerber, T. I. A., Luzipo, D. & Mayer, P. (2004). J. Coord. Chem. 57, 1345-1349.]). Graziani et al. (1985[Graziani, R., Casellato, U., Rossi, R. & Marchi, A. (1985). J. Crystallogr. Spectrosc. Res. 15, 573-579.]); Herrman et al. (1990[Herrman, W. A., Thiel, W. R. & Hardtweck, E. (1990). Chem. Ber. 123, 271-276.]); Irmler et al. (1991[Irmler, M., Möller, A. & Meyer, G. (1991). Z. Anorg. Allg. Chem. 604, 7-26.]); Lebuis et al. (1993[Lebuis, A. M., Roux, C. & Beauchamp, A. L. (1993). Can. J. Chem. 71, 441-449.]); Mrozinski et al. (2002[Mrozinski, J., Kochel, A. & Lis, T. (2002). J. Mol. Struct. 610, 53-58.]); Quintal et al. (2000[Quintal, S. M. Q., Nogueira, H. I. S., Felix, V. & Drew, M. G. B. (2000). New J. Chem. 24, 511-517.]); Schmidt-Brucken & Abram (2000[Schmidt-Brucken, B. & Abram, U. (2000). Z. Anorg. Allg. Chem. 626, 951-958.]). For further synthetic details, see: Watt & Thompson (1963[Watt, G. W. & Thompson, R. J. (1963). Inorg. Synth. 7, 190-192.]).

[Scheme 1]

Experimental

Crystal data

  • [Re(C3H7O)I2O(C8H6N4)]

  • Mr = 673.26

  • Monoclinic, P 21 /c

  • a = 10.3973 (3) Å

  • b = 10.9046 (3) Å

  • c = 15.6341 (6) Å

  • β = 117.616 (2)°

  • V = 1570.63 (9) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 11.67 mm−1

  • T = 100 K

  • 0.12 × 0.11 × 0.03 mm
Data collection

  • Oxford Diffraction KM-4-CCD diffractometer

  • Absorption correction: analytical (CrysAlis RED; Oxford Diffraction, 2007[Oxford Diffraction (2007). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]) Tmin = 0.456, Tmax = 0.611

  • 15982 measured reflections

  • 2776 independent reflections

  • 2288 reflections with I > 2σ(I)

  • Rint = 0.050
Refinement

  • R[F2 > 2σ(F2)] = 0.029

  • wR(F2) = 0.056

  • S = 1.03

  • 2776 reflections

  • 183 parameters

  • H-atom parameters constrained

  • Δρmax = 1.85 e Å−3

  • Δρmin = −1.34 e Å−3

Table 1
Selected geometric parameters (Å, °)

Re1—O1 1.698 (4)
Re1—O2 1.861 (5)
Re1—N1 2.175 (5)
Re1—N2 2.183 (6)
Re1—I1 2.7176 (5)
Re1—I2 2.7235 (5)
N1—Re1—N2 76.5 (2)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
C1—H1⋯I1 0.95 3.04 3.697 (7) 127
C6—H6⋯I2 0.95 3.05 3.709 (7) 128
C5—H5⋯N4i 0.95 2.58 3.504 (9) 163
C6—H6⋯O1ii 0.95 2.53 3.193 (9) 127
C9—H9⋯I1iii 1.00 3.02 3.834 (8) 139
Symmetry codes: (i) [-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]; (ii) -x+1, -y-1, -z; (iii) [x, -y-{\script{1\over 2}}, z+{\script{1\over 2}}].

Data collection: CrysAlis CCD (Oxford Diffraction, 2007[Oxford Diffraction (2007). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]); cell refinement: CrysAlis RED (Oxford Diffraction, 2007[Oxford Diffraction (2007). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]); data reduction: CrysAlis RED; 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: DIAMOND (Brandenburg & Putz, 2005[Brandenburg, K. & Putz, H. (2005). DIAMOND. Crystal Impact GbR, Bonn, Germany.]); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809052556/hb5231sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809052556/hb5231Isup2.hkl

checkCIF report


Comment top

ReV complexes have been research object for many authors during the last years. Complexes of general formula [ReOX2(C5H4N)CH(O)CH2(C5H4N)] (X = Cl, I) were obtained by a reaction of trans-[ReOCl3(PPh3)2] and trans-[ReOI2(OEt)(PPh3)2] with cis-1,2-di-(2-pyridyl)ethylene (DPE) in ethanol and in benzene on air. The coordinated DPE ligand undergoes addition of water at the ethylene carbon atoms, and the (C5H4N)CH(O)CH2(C5H4N) moiety acts as terdentate N,O,N-donor ligand. X-ray crystal structures of both complexes have been determined and show distorted octahedral geometry around the rhenium(V) centre (Abrahams et al., 2005). Complexes cis-[ReOX2(msa)(PPh3)] [X = Cl(1), I(2)] were prepared from trans-[ReOCl3(PPh3)2] or trans-[ReOI2(OEt)(PPh3)2] in reaction with 2-(1-iminoethyl)phenol (Hmsa) in acetonitrile. X-ray crystal structure shows, that the bonding distances and angles in 1 and 2 are nearly identical, and that the two halide ligands in each complex are coordinated cis to each other in the equatorial plane cis to the oxido group. Rhenium(V) complexes with two iodido ligands cis to each other are rare (Abrahams et al., 2007). Rhenium(V) complexes with trans-O—Re-(2-propoxido) core are known. Rhenium(V) complex with 2-propoxido ligand of formula [ReOCl2(C3H7O)(Ph3P)2] has been synthesized (Abram et al. 1995), and the other one, [ReClO(C3H7O)PPh3L] (where L = pyridine-2-thiolato ligand), was obtained (Schmidt-Brucken & Abram, 2000). This paper contains a report on the synthesis and structure of the first characterized [ReOI2(C3H7O)(2–2?bipyrimidine)] 1 complex with ReI2 core and 2-propoxido ligand. Fig. 1 presents the view of molecular structure of compound 1, the compound crystallizes in monoclinic crystal system in P21/c space group. The compound was obtained in the synthesis with (NH4)2ReI6 and 2,2'-bipyrimidine as substrates in a mixture of 2-propanol and acetone. The environment around the metal center is a distorted octahedron, with two iodido ligands, 2-propoxido ligand and 2,2'-bipyrimidine ligand coordinated via nitrogen atoms. The Re—I bond lengths are Re1—I1 2.7176 (5) Å, Re1—I2 2.7235 (5) Å, respectively,similar Re—I distances were observed in 2-(2-aminophenyl)ethanolato-N,O)-bis(iododo)-oxido- triphenylphosphine-rhenium(V) and diodido-(3-hydroxidopicolinato)-oxido-)-triphenylphosphine-rhenium(II) (Gerber et al., 2004, Quintal et al., 2000). On the other hand, the Re1—O1 1.698 (4) Å bond length is characteristic for monooxido-rhenium(V) complexes (on average 1.69%A), which is in agreement with the situation in the comparable complexes (Graziani et al., 1985, Lebuis et al., 1993). The O atom from 2-propoxido ligand is coordinated to the rhenium atom with Re—O2 1.861 (5) Å; this bond is remarkably short with the same multiple bond character as discussed (Ciani et al. 1983). The O—Re—O unit is nearly linear with an angle of 169.69 (3)°. Moreover, a molecule of 2,2'-bipyrimidine is coordinated with Re—N bond length of Re1—N1 2.175 (5) %A, Re1—N2 2.183 (6) Å, which is comparable to the previously investigated trans-[ReCl4(py)2] (Mrozinski et al., 2002, Herrman et al., 1990). Re atom lies within the plane of I1, I2, N1, N2 atoms, the N1—Re1—O1 and N2—Re1—O1 angles are 88.63 (19), 86.93 (14) and N1—Re1—O2, N2—Re1—O2 83.37 (14) and 84.87 (15) and are directed in side to 2,2'-bipyrimidine. The rings of the 4,4'-bpy ligand are coplanar with the plane defined by the I ligands, one of the Re—N bond is shorter (Re1—N1 2.175 (5) Å, Re1—N2 2.183 (6) Å), which may be a result of iodido ligand presence. The molecule conformation is stabilized by intramolecular hydrogen bonds C(1)—H(1)···I(1) and C(6)—-H(6)···I(2), as well as by the intermolecular hydrogen bonds of C—H···O and C—H···N type. All hydrogen bonds are summarized in Table 2. In the crystal structure packing along [100] and [010] a layered arrangement of the molecules could be observed. The crystal structure packing viewed along [100] direction is illustrated in Fig. 2. In the structure the stacking interactions are observed. pi-pi stacking interactions between the 2,2'-bypirymidine rings contribute to forming a supramolecular network structure (Fig. 2). The centroid-centroid distance of the adjacent aromatic rings is about 3.58%A, indicating a normal pi-pi interaction. The corresponding TG-DTA curves (the measurement was carried out under nitrogen atmosphere) for the title compound (Fig. 3) show a three-step decomposition process and that the compound is very stable during heating. In the first step of the thermal decomposition process weight loss in the temperature range 242–247°C of 1.39% (calc. 1.43%) is observed. In DTA curve, this decomposition is visible as an endothermic peak at temperature 247°C, indicating the presence of coordinated 4.4,-bipyrimidine (corresponding to the weight loss of 1.39% in thermal decomposition, which is in agreement with the calculated value of 1.43%). Further weight losses correspond to decomposition of further compound parts, they are continuous and are difficult for unambiguous interpretation (decomposition of all compound constituents except for rhenium part). Another peak at 800°C is also observed, however, it is difficult to interpret. It is possible, that the decomposition process leads to rhenium oxides. Similar decomposition process through many intermediate stages has been observed for (NH4)2[Re3Cl12] (Irmler et al., 1991). In conclusion, an interesting rhenium(V) trans-2,2,-bipyrimidine-diiodido-oxido-(2-propoxido)-rhenium(V) complex with 2-propoxido ligand was obtained. The crystal structure is stabilized by hydrogen bonding interactions. This is the first structural report confirming the existence of a iodido rhenium complex with an aromatic amine and 2-propoxido ligand in coordination sphere.

Related literature top

For related structures and for further discussion of rhenium structural chemistry, see: Abrahams et al. (2005, 2007); Abram et al. (1995); Ciani et al. (1983); Gerber et al. (2004). Graziani et al. (1985); Herrman et al. (1990); Irmler et al. (1991); Lebuis et al. (1993); Mrozinski et al. (2002); Quintal et al. (2000); Schmidt-Brucken & Abram (2000). For further synthetic details, see: Watt & Thompson (1963).

Experimental top

A mixture of (NH4)2[ReI6] (prepared according to the literature procedure (Watt & Thompson, 1963) (0.12 g) and 0.30 g of 2,2,-(bipyrimidine) (from Aldrich) was added to a mixture of 2-propanol/acetone (1:1) (50 cm3) and then was stirred at 40° for about 4 h, the color of the solution was dark green. The solution was left for slow crystallization by evaporation under parafilm. The mixture was kept at room temperature for crystallization. After five days the pale green plate-shaped crystals were obtained. Anal. Calc. For: [ReOI2(C3H7O)(2,2,bipyrimidine)] C 19.62, H 2.08, N 8.32, I 37.69%: found C 19.01, H 1.89, N 8.15, I 37.50%. Selected IR data (KBr): 2925 (m), 2854 (m), 1717 (m), 1631 (m), 1610 (w), 1558 (s), 1464 (m), 1406 (s),1378 (m), 1271 (w), 1193 (w), 1191 (w), 978 (w), 908(w), 807 (w),645 (m), 561 (w), 535 (w), 452 (s), 390 (w), 358(w), 315 (s), 162 (versus), 131 (s), 74 (w).

TG–DTA Thermogravimetric measurements were carried out using a TG–DTA SETSYS 16Y18 device under nitrogen atmosphere for a sample placed in Al2O3 crucible. The investigated temperature range was from room temperature to 1400°C at 10°C/min. temperature changes rate. IR spectra The room temperature FT—IR spectra of polycrystalline samples were measured by means of the Bruker IFS-66 instrument.

Refinement top

The H atoms were generated geometrically and refined using a riding model, with C—H = 0.95 Å and Uiso(H) = 1.2 Ueq(C). The highest peak of 0.82 electrons at the difference Fourier map was situated near the Re atom.

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2007); cell refinement: CrysAlis RED (Oxford Diffraction, 2007); data reduction: CrysAlis RED (Oxford Diffraction, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg & Putz, 2005); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. View of (I) showing 50% displacement ellipsoids (H atoms as spheres of arbitrary radius).
[Figure 2] Fig. 2. The crystal packing in (I) viewed down [100].
[Figure 3] Fig. 3. Corresponding TG/DTA curves for 1. The thicker line denotes the thermal effect, the thinner line denotes the weight loss curve.
trans-(2,2'-Bipyrimidine)diiodido(isopropoxido)oxidorhenium(V) top
Crystal data top
[Re(C3H7O)I2O(C8H6N4)]F(000) = 1216
Mr = 673.26Dx = 2.847 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 2115 reflections
a = 10.3973 (3) Åθ = 2.9–25.1°
b = 10.9046 (3) ŵ = 11.67 mm−1
c = 15.6341 (6) ÅT = 100 K
β = 117.616 (2)°Plate, pale green
V = 1570.63 (9) Å30.12 × 0.11 × 0.03 mm
Z = 4
Data collection top
Oxford Diffraction KM-4-CCD
diffractometer		2776 independent reflections
Radiation source: fine-focus sealed tube2288 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.050
/w scansθmax = 25.1°, θmin = 2.9°
Absorption correction: analytical
(CrysAlis RED; Oxford Diffraction, 2007)		h = −12→12
Tmin = 0.456, Tmax = 0.611k = −11→12
15982 measured reflectionsl = −18→18
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)] = 0.029Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.056H-atom parameters constrained
S = 1.03 w = 1/[σ2(Fo2) + (0.0251P)2 + 3.8665P]
where P = (Fo2 + 2Fc2)/3
2776 reflections(Δ/σ)max = 0.001
183 parametersΔρmax = 1.85 e Å−3
0 restraintsΔρmin = −1.34 e Å−3
Crystal data top
[Re(C3H7O)I2O(C8H6N4)]V = 1570.63 (9) Å3
Mr = 673.26Z = 4
Monoclinic, P21/cMo Kα radiation
a = 10.3973 (3) ŵ = 11.67 mm−1
b = 10.9046 (3) ÅT = 100 K
c = 15.6341 (6) Å0.12 × 0.11 × 0.03 mm
β = 117.616 (2)°
Data collection top
Oxford Diffraction KM-4-CCD
diffractometer		2776 independent reflections
Absorption correction: analytical
(CrysAlis RED; Oxford Diffraction, 2007)		2288 reflections with I > 2σ(I)
Tmin = 0.456, Tmax = 0.611Rint = 0.050
15982 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0290 restraints
wR(F2) = 0.056H-atom parameters constrained
S = 1.03Δρmax = 1.85 e Å−3
2776 reflectionsΔρmin = −1.34 e Å−3
183 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
Re10.26746 (3)−0.33250 (2)−0.10973 (2)0.02512 (9)
I10.13432 (6)−0.31460 (4)−0.30538 (3)0.03659 (14)
I20.22482 (5)−0.57955 (4)−0.12777 (3)0.03021 (13)
O10.4380 (5)−0.3317 (4)−0.0984 (3)0.0228 (10)
O20.0941 (5)−0.3139 (4)−0.1035 (3)0.0317 (11)
N10.2890 (6)−0.1369 (5)−0.0790 (4)0.0228 (12)
N20.3689 (7)−0.3247 (5)0.0476 (4)0.0281 (13)
N30.3837 (7)0.0063 (5)0.0504 (4)0.0293 (14)
N40.4828 (7)−0.1874 (5)0.1792 (4)0.0316 (15)
C10.2343 (8)−0.0453 (6)−0.1436 (5)0.0324 (17)
H10.1832−0.0636−0.21050.039*
C20.2519 (9)0.0735 (6)−0.1134 (5)0.0365 (19)
H20.21140.1388−0.15830.044*
C30.3303 (8)0.0959 (6)−0.0157 (5)0.0328 (18)
H30.34730.17860.00570.039*
C40.5150 (9)−0.2833 (6)0.2389 (5)0.0342 (18)
H40.5655−0.26900.30650.041*
C50.4775 (8)−0.4035 (6)0.2062 (5)0.0320 (17)
H50.5002−0.47040.24980.038*
C60.4065 (8)−0.4201 (6)0.1084 (5)0.0273 (16)
H60.3834−0.50090.08300.033*
C70.3584 (8)−0.1071 (6)0.0158 (5)0.0291 (17)
C80.4078 (8)−0.2118 (6)0.0862 (5)0.0261 (16)
C9−0.0043 (9)−0.2989 (8)−0.0654 (6)0.045 (2)
H90.0494−0.31590.00550.054*
C10−0.1237 (9)−0.3889 (8)−0.1089 (6)0.043 (2)
H10A−0.1895−0.3648−0.17540.065*
H10B−0.1773−0.3915−0.07130.065*
H10C−0.0834−0.4703−0.10870.065*
C11−0.0531 (8)−0.1652 (6)−0.0783 (6)0.0382 (18)
H11A0.0309−0.1123−0.04160.057*
H11B−0.1249−0.1540−0.05490.057*
H11C−0.0966−0.1434−0.14690.057*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Re10.03734 (18)0.00899 (14)0.03104 (16)0.00073 (12)0.01756 (13)0.00019 (11)
I10.0430 (3)0.0213 (3)0.0286 (2)0.0025 (2)0.0023 (2)0.0026 (2)
I20.0453 (3)0.0095 (2)0.0337 (3)−0.00078 (19)0.0165 (2)−0.00140 (18)
O10.031 (3)0.015 (2)0.022 (2)0.0001 (19)0.011 (2)−0.0019 (19)
O20.041 (3)0.016 (2)0.041 (3)0.002 (2)0.022 (3)−0.001 (2)
N10.030 (3)0.013 (3)0.028 (3)0.001 (2)0.016 (3)0.000 (2)
N20.045 (4)0.012 (3)0.034 (3)0.001 (3)0.025 (3)0.001 (3)
N30.056 (4)0.012 (3)0.036 (3)−0.005 (3)0.035 (3)−0.004 (3)
N40.065 (4)0.018 (3)0.027 (3)−0.003 (3)0.034 (3)−0.001 (2)
C10.049 (5)0.016 (4)0.029 (4)0.008 (3)0.015 (4)0.002 (3)
C20.062 (5)0.011 (4)0.045 (5)0.005 (4)0.033 (4)0.009 (3)
C30.061 (5)0.006 (3)0.050 (5)−0.002 (3)0.042 (4)−0.002 (3)
C40.065 (6)0.021 (4)0.025 (4)−0.001 (4)0.028 (4)0.000 (3)
C50.055 (5)0.024 (4)0.030 (4)0.004 (3)0.030 (4)0.001 (3)
C60.043 (5)0.010 (3)0.038 (4)−0.002 (3)0.026 (4)−0.003 (3)
C70.048 (5)0.011 (4)0.044 (4)−0.002 (3)0.034 (4)−0.004 (3)
C80.045 (5)0.010 (3)0.037 (4)−0.001 (3)0.030 (4)−0.001 (3)
C90.042 (5)0.045 (5)0.039 (4)0.004 (4)0.013 (4)−0.004 (4)
C100.041 (5)0.050 (5)0.039 (4)−0.010 (4)0.019 (4)−0.009 (4)
C110.034 (4)0.026 (4)0.051 (5)0.007 (3)0.016 (4)0.001 (4)
Geometric parameters (Å, º) top
Re1—O11.698 (4)C2—H20.9500
Re1—O21.861 (5)C3—H30.9500
Re1—N12.175 (5)C4—C51.395 (10)
Re1—N22.183 (6)C4—H40.9500
Re1—I12.7176 (5)C5—C61.368 (10)
Re1—I22.7235 (5)C5—H50.9500
O2—C91.411 (10)C6—H60.9500
N1—C11.345 (8)C7—C81.502 (10)
N1—C71.353 (9)C9—C101.478 (11)
N2—C61.339 (8)C9—C111.526 (10)
N2—C81.348 (8)C9—H91.0000
N3—C71.326 (8)C10—H10A0.9800
N3—C31.341 (9)C10—H10B0.9800
N4—C81.320 (9)C10—H10C0.9800
N4—C41.337 (9)C11—H11A0.9800
C1—C21.361 (10)C11—H11B0.9800
C1—H10.9500C11—H11C0.9800
C2—C31.380 (10)
O1—Re1—O2169.68 (19)N4—C4—C5122.8 (6)
O1—Re1—N188.66 (19)N4—C4—H4118.6
O2—Re1—N183.34 (19)C5—C4—H4118.6
O1—Re1—N286.9 (2)C6—C5—C4116.6 (6)
O2—Re1—N284.9 (2)C6—C5—H5121.7
N1—Re1—N276.5 (2)C4—C5—H5121.7
O1—Re1—I194.56 (13)N2—C6—C5121.3 (6)
O2—Re1—I192.91 (15)N2—C6—H6119.4
N1—Re1—I197.18 (14)C5—C6—H6119.4
N2—Re1—I1173.47 (14)N3—C7—N1125.1 (6)
O1—Re1—I297.35 (14)N3—C7—C8118.3 (6)
O2—Re1—I289.91 (13)N1—C7—C8116.6 (6)
N1—Re1—I2171.11 (14)N4—C8—N2125.3 (6)
N2—Re1—I297.22 (14)N4—C8—C7118.7 (6)
I1—Re1—I288.908 (16)N2—C8—C7115.9 (6)
C9—O2—Re1160.7 (5)O2—C9—C10110.3 (6)
C1—N1—C7118.0 (5)O2—C9—C11108.4 (7)
C1—N1—Re1126.7 (4)C10—C9—C11114.6 (7)
C7—N1—Re1115.2 (4)O2—C9—H9107.7
C6—N2—C8117.7 (6)C10—C9—H9107.7
C6—N2—Re1126.8 (4)C11—C9—H9107.7
C8—N2—Re1115.3 (4)C9—C10—H10A109.5
C7—N3—C3115.6 (6)C9—C10—H10B109.5
C8—N4—C4116.2 (6)H10A—C10—H10B109.5
N1—C1—C2120.3 (7)C9—C10—H10C109.5
N1—C1—H1119.8H10A—C10—H10C109.5
C2—C1—H1119.8H10B—C10—H10C109.5
C1—C2—C3117.9 (7)C9—C11—H11A109.5
C1—C2—H2121.1C9—C11—H11B109.5
C3—C2—H2121.1H11A—C11—H11B109.5
N3—C3—C2123.1 (6)C9—C11—H11C109.5
N3—C3—H3118.5H11A—C11—H11C109.5
C2—C3—H3118.5H11B—C11—H11C109.5
O1—Re1—O2—C9−37 (2)C1—C2—C3—N3−3.1 (11)
N1—Re1—O2—C9−76.5 (14)C8—N4—C4—C52.4 (11)
N2—Re1—O2—C90.5 (14)N4—C4—C5—C60.8 (11)
I1—Re1—O2—C9−173.4 (14)C8—N2—C6—C52.2 (10)
I2—Re1—O2—C997.7 (14)Re1—N2—C6—C5176.0 (5)
O1—Re1—N1—C1100.5 (6)C4—C5—C6—N2−3.2 (10)
O2—Re1—N1—C1−86.0 (6)C3—N3—C7—N12.4 (10)
N2—Re1—N1—C1−172.3 (6)C3—N3—C7—C8−176.6 (6)
I1—Re1—N1—C16.1 (6)C1—N1—C7—N3−3.6 (10)
O1—Re1—N1—C7−83.2 (5)Re1—N1—C7—N3179.7 (5)
O2—Re1—N1—C790.2 (5)C1—N1—C7—C8175.4 (6)
N2—Re1—N1—C73.9 (4)Re1—N1—C7—C8−1.3 (7)
I1—Re1—N1—C7−177.7 (4)C4—N4—C8—N2−3.7 (11)
O1—Re1—N2—C6−91.0 (6)C4—N4—C8—C7175.4 (6)
O2—Re1—N2—C695.2 (6)C6—N2—C8—N41.5 (11)
N1—Re1—N2—C6179.6 (6)Re1—N2—C8—N4−173.1 (6)
I2—Re1—N2—C66.0 (6)C6—N2—C8—C7−177.6 (6)
O1—Re1—N2—C883.0 (5)Re1—N2—C8—C77.8 (8)
O2—Re1—N2—C8−90.8 (5)N3—C7—C8—N4−4.5 (10)
N1—Re1—N2—C8−6.4 (5)N1—C7—C8—N4176.4 (6)
I2—Re1—N2—C8180.0 (5)N3—C7—C8—N2174.7 (6)
C7—N1—C1—C21.3 (11)N1—C7—C8—N2−4.4 (9)
Re1—N1—C1—C2177.5 (5)Re1—O2—C9—C10−130.8 (12)
N1—C1—C2—C31.8 (11)Re1—O2—C9—C11102.9 (14)
C7—N3—C3—C21.1 (10)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C1—H1···I10.953.043.697 (7)127
C6—H6···I20.953.053.709 (7)128
C5—H5···N4i0.952.583.504 (9)163
C6—H6···O1ii0.952.533.193 (9)127
C9—H9···I1iii1.003.023.834 (8)139
Symmetry codes: (i) −x+1, y−1/2, −z+1/2; (ii) −x+1, −y−1, −z; (iii) x, −y−1/2, z+1/2.

Experimental details

Crystal data
Chemical formula[Re(C3H7O)I2O(C8H6N4)]
Mr673.26
Crystal system, space groupMonoclinic, P21/c
Temperature (K)100
a, b, c (Å)10.3973 (3), 10.9046 (3), 15.6341 (6)
β (°) 117.616 (2)
V (Å3)1570.63 (9)
Z4
Radiation typeMo Kα
µ (mm−1)11.67
Crystal size (mm)0.12 × 0.11 × 0.03
Data collection
DiffractometerOxford Diffraction KM-4-CCD
diffractometer
Absorption correctionAnalytical
(CrysAlis RED; Oxford Diffraction, 2007)
Tmin, Tmax0.456, 0.611
No. of measured, independent and
observed [I > 2σ(I)] reflections		15982, 2776, 2288
Rint0.050
(sin θ/λ)max (Å−1)0.596
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.029, 0.056, 1.03
No. of reflections2776
No. of parameters183
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å−3)1.85, −1.34

Computer programs: CrysAlis CCD (Oxford Diffraction, 2007), CrysAlis RED (Oxford Diffraction, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), DIAMOND (Brandenburg & Putz, 2005).

Selected geometric parameters (Å, º) top
Re1—O11.698 (4)Re1—N22.183 (6)
Re1—O21.861 (5)Re1—I12.7176 (5)
Re1—N12.175 (5)Re1—I22.7235 (5)
N1—Re1—N276.5 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C1—H1···I10.953.043.697 (7)127
C6—H6···I20.953.053.709 (7)128
C5—H5···N4i0.952.583.504 (9)163
C6—H6···O1ii0.952.533.193 (9)127
C9—H9···I1iii1.003.023.834 (8)139
Symmetry codes: (i) −x+1, y−1/2, −z+1/2; (ii) −x+1, −y−1, −z; (iii) x, −y−1/2, z+1/2.
 

Acknowledgements

Financial support by the Polish Ministry of Science and Higher Education (grant No. N N204 016735, in years 2008–2010) is gratefully acknowledged

References

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ISSN: 2056-9890
Volume 66| Part 1| January 2010| Pages m42-m43
doi:10.1107/S1600536809052556
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