supplementary materials


HTML versionpdf versioncif file3d viewstructure factorssupplementary materialsCIF check reportcited insimilar papers Open access

Acta Cryst. (2009). E65, m1395    [ doi:10.1107/S1600536809042160 ]

Tetraethylammonium tricarbonylchlorido(pyrazine-2-carboxylato-N1,O)rhenate(I)

J. Suthiram, K. Mhlaba, J. R. Zeevaart, H. G. Visser and A. Roodt

Abstract top

In the title complex, (C8H20N)[Re(C5H3N2O2)Cl(CO)3], the ReI atom is coordinated facially by three carbonyl groups; the bidentate pyrazinecarboxylato ligand and a chlorine atom complete the distorted octahedral coordination.

Comment top

The title complex, (I), forms a part of an ongoing investigation of the structural and kinetic behaviour of fac-Re(CO)3 compounds (Schutte et al., 2008). It crystallized as an anionic ReI compound and one tetraethylammonium counter ion in the asymmetric unit (Fig. 1). The Re—CO bond distances are well within the normal range (Allen et al., 1987). The small bite angle O4—Re1—N1 might be a reason for the slightly distorted octahedral geometry around the metal centre. There are no classical hydrogen bonds in the structure.

Related literature top

For synthetic background, see: Alberto et al. (1996). For related structures, see: Schutte et al. (2008); Kemp (2006); Wang et al. (2003); Alvarez et al. (2007); Brasey et al. (2004); Mundwiler et al. (2004). For bond-length data, see: Allen et al. (1987).

Experimental top

ReCl3(CO)3 (64.2 mg, 0.01 mmol) was suspended in 10 ml methanol. The solution was heated to reflux and 2-pyrazinecarboxylic acid (13.1 mg, 0.01 mmol) dissolved in ca 5 ml methanol was added whilst stirring. A bright yellow colour resulted on addition of the ligand to the metal. K2CO3 7.1 mg (0.005 mmol) was added to the solution. The reaction solution was refluxed for 6 h after which the solvent volume was decreased on a rotovapor. The MeOH solution was layered with a minimal amount of diethyl ether and left to stand in a refrigerator. After a few days yellow crystals were formed.

Refinement top

The methyl, methylene and aromatic H atoms were placed in geometrically idealized positions with C—H distances = 0.96, 0.97 and 0.96 Å, respectively, and constrained to ride on their parent atoms, with Uiso(H) = 1.5Ueq(methyl-C) and 1.2Ueq(methylene and aromatic-C). The highest residual electron density was located 0.93 Å from H17C and was essentially meaningless.

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT-Plus (Bruker, 2004); data reduction: SAINT-Plus and XPREP (Bruker, 2004); 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: WinGX (Farrugia, 1999).

Figures top
[Figure 1] Fig. 1. A view of the title complex plotted with 50% probability displacement ellipsoids; hydrogen atoms have been omitted for clarity.
Tetraethylammonium tricarbonylchlorido(pyrazine-2-carboxylato-N1,O)rhenate(I) top
Crystal data top
(C8H20N)[Re(C5H3N2O2)Cl(CO)3]F(000) = 1088
Mr = 559.02Dx = 1.929 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 9901 reflections
a = 7.927 (5) Åθ = 2.7–28.3°
b = 22.278 (5) ŵ = 6.48 mm−1
c = 10.903 (5) ÅT = 100 K
β = 90.506 (5)°Cuboid, yellow
V = 1925.4 (16) Å30.27 × 0.20 × 0.11 mm
Z = 4
Data collection top
Bruker X8 APEXII 4K Kappa CCD
diffractometer		4781 independent reflections
Radiation source: sealed tube4121 reflections with I > 2σ(I)
graphiteRint = 0.046
phi and ω scansθmax = 28.3°, θmin = 1.8°
Absorption correction: multi-scan
(SADABS; Bruker, 2004)		h = −10→9
Tmin = 0.273, Tmax = 0.539k = −29→29
32482 measured reflectionsl = −14→13
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.021 w = 1/[σ2(Fo2) + (0.0591P)2]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.098(Δ/σ)max = 0.001
S = 1.18Δρmax = 1.05 e Å−3
4781 reflectionsΔρmin = −1.38 e Å−3
235 parameters
Crystal data top
(C8H20N)[Re(C5H3N2O2)Cl(CO)3]V = 1925.4 (16) Å3
Mr = 559.02Z = 4
Monoclinic, P21/cMo Kα radiation
a = 7.927 (5) ŵ = 6.48 mm−1
b = 22.278 (5) ÅT = 100 K
c = 10.903 (5) Å0.27 × 0.20 × 0.11 mm
β = 90.506 (5)°
Data collection top
Bruker X8 APEXII 4K Kappa CCD
diffractometer		4781 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2004)		4121 reflections with I > 2σ(I)
Tmin = 0.273, Tmax = 0.539Rint = 0.046
32482 measured reflectionsθmax = 28.3°
Refinement top
R[F2 > 2σ(F2)] = 0.021H-atom parameters constrained
wR(F2) = 0.098Δρmax = 1.05 e Å−3
S = 1.18Δρmin = −1.38 e Å−3
4781 reflectionsAbsolute structure: ?
235 parametersFlack parameter: ?
0 restraintsRogers parameter: ?
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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Re10.30393 (2)0.198197 (7)0.407485 (15)0.01064 (8)
Cl10.29768 (13)0.09512 (5)0.49378 (10)0.0154 (2)
C50.3651 (5)0.13259 (19)0.1726 (4)0.0117 (8)
O50.0904 (4)0.10473 (15)0.1121 (3)0.0186 (7)
N30.1752 (4)−0.07955 (16)0.2734 (3)0.0111 (7)
O40.1219 (4)0.16145 (14)0.2811 (3)0.0143 (7)
N20.6136 (5)0.10700 (19)0.0608 (4)0.0198 (9)
N10.4559 (5)0.15900 (16)0.2633 (3)0.0132 (8)
C140.1057 (5)−0.0443 (2)0.1656 (4)0.0146 (9)
H14B0.1568−0.00470.16660.018*
H14A0.1403−0.0640.09060.018*
C40.1762 (5)0.1323 (2)0.1880 (4)0.0131 (9)
C100.1294 (6)−0.0471 (2)0.3912 (4)0.0169 (9)
H10A0.1667−0.00580.38490.02*
H10B0.0075−0.04670.39830.02*
C15−0.0836 (6)−0.0368 (2)0.1619 (4)0.0182 (10)
H15B−0.1153−0.01380.09090.027*
H15C−0.1197−0.01640.23450.027*
H15A−0.1361−0.07560.15780.027*
C120.3647 (5)−0.0855 (2)0.2602 (4)0.0147 (9)
H12B0.4069−0.11060.32640.018*
H12A0.3875−0.10620.18380.018*
C170.1141 (6)−0.1786 (2)0.1620 (5)0.0215 (10)
H17B0.0637−0.21730.17390.032*
H17A0.231−0.18350.14180.032*
H17C0.0569−0.15810.09620.032*
C10.4817 (6)0.2209 (2)0.5162 (4)0.0160 (9)
C70.7019 (6)0.1324 (2)0.1527 (4)0.0187 (10)
H70.8190.13230.1490.022*
C160.0997 (6)−0.14213 (19)0.2785 (4)0.0139 (9)
H16A0.1545−0.16410.34450.017*
H16B−0.0188−0.13860.29880.017*
C130.4627 (6)−0.0272 (2)0.2612 (5)0.0228 (11)
H13C0.5808−0.03550.25250.034*
H13B0.4444−0.00670.33740.034*
H13A0.425−0.00230.19450.034*
C80.6250 (6)0.1586 (2)0.2526 (4)0.0167 (9)
H80.69130.17640.31340.02*
C60.4450 (6)0.1077 (2)0.0729 (4)0.0169 (9)
H60.37910.09060.01110.02*
C110.2032 (6)−0.0737 (2)0.5073 (4)0.0227 (11)
H11B0.1677−0.05040.57650.034*
H11A0.3241−0.07330.50280.034*
H11C0.1646−0.11430.51620.034*
C30.1409 (6)0.2291 (2)0.5218 (4)0.0148 (9)
O20.3224 (4)0.32482 (15)0.2989 (3)0.0206 (7)
O30.0411 (4)0.24882 (16)0.5855 (3)0.0215 (7)
O10.5931 (4)0.23294 (16)0.5808 (3)0.0241 (8)
C20.3140 (5)0.2765 (2)0.3371 (4)0.0139 (9)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Re10.01130 (11)0.00960 (12)0.01101 (12)−0.00026 (6)−0.00005 (7)−0.00013 (6)
Cl10.0170 (5)0.0123 (5)0.0169 (5)−0.0006 (4)−0.0002 (4)0.0005 (4)
C50.013 (2)0.010 (2)0.012 (2)0.0021 (16)−0.0005 (16)0.0015 (16)
O50.0130 (16)0.0202 (19)0.0227 (17)−0.0029 (13)−0.0034 (13)−0.0071 (14)
N30.0113 (17)0.0110 (18)0.0110 (17)−0.0010 (14)0.0013 (13)0.0012 (14)
O40.0127 (15)0.0161 (17)0.0141 (15)−0.0004 (12)−0.0006 (12)−0.0029 (13)
N20.017 (2)0.026 (2)0.0168 (19)0.0039 (17)0.0031 (16)0.0009 (17)
N10.0121 (17)0.0103 (19)0.0172 (19)−0.0001 (14)0.0000 (14)0.0036 (15)
C140.015 (2)0.013 (2)0.015 (2)0.0012 (17)0.0014 (17)0.0052 (17)
C40.011 (2)0.013 (2)0.015 (2)0.0013 (16)0.0001 (16)0.0019 (17)
C100.014 (2)0.017 (2)0.019 (2)0.0022 (18)0.0026 (18)−0.0043 (19)
C150.015 (2)0.024 (3)0.016 (2)0.0029 (19)−0.0025 (17)0.0024 (19)
C120.010 (2)0.017 (2)0.018 (2)0.0019 (17)0.0027 (16)−0.0006 (18)
C170.023 (3)0.020 (3)0.022 (3)0.000 (2)0.002 (2)−0.005 (2)
C10.023 (2)0.009 (2)0.016 (2)0.0009 (18)0.0019 (18)−0.0015 (18)
C70.010 (2)0.026 (3)0.021 (2)0.0035 (18)0.0040 (17)0.006 (2)
C160.014 (2)0.010 (2)0.017 (2)−0.0034 (17)0.0005 (17)0.0017 (18)
C130.012 (2)0.022 (3)0.034 (3)−0.0006 (19)0.000 (2)0.004 (2)
C80.015 (2)0.018 (2)0.017 (2)0.0012 (18)−0.0034 (17)0.0026 (18)
C60.015 (2)0.019 (3)0.017 (2)−0.0002 (18)−0.0019 (17)0.0016 (18)
C110.024 (3)0.029 (3)0.015 (2)0.002 (2)−0.0004 (19)−0.005 (2)
C30.018 (2)0.012 (2)0.015 (2)−0.0024 (17)−0.0025 (18)0.0039 (18)
O20.0225 (18)0.0123 (17)0.0272 (19)−0.0016 (14)0.0033 (15)0.0027 (15)
O30.0279 (18)0.0198 (19)0.0170 (17)0.0012 (15)0.0096 (14)−0.0011 (14)
O10.0222 (18)0.021 (2)0.0284 (19)0.0010 (15)−0.0097 (15)−0.0060 (16)
C20.012 (2)0.018 (2)0.012 (2)0.0026 (17)0.0006 (16)−0.0006 (18)
Geometric parameters (Å, °) top
Re1—C11.902 (5)C15—H15C0.96
Re1—C21.908 (5)C15—H15A0.96
Re1—C31.930 (5)C12—C131.514 (6)
Re1—O42.149 (3)C12—H12B0.97
Re1—N12.172 (4)C12—H12A0.97
Re1—Cl12.4822 (12)C17—C161.513 (6)
C5—N11.353 (6)C17—H17B0.96
C5—C61.379 (6)C17—H17A0.96
C5—C41.508 (6)C17—H17C0.96
O5—C41.231 (5)C1—O11.156 (5)
N3—C141.514 (5)C7—C81.383 (7)
N3—C121.517 (5)C7—H70.93
N3—C161.518 (5)C16—H16A0.97
N3—C101.521 (5)C16—H16B0.97
O4—C41.282 (5)C13—H13C0.96
N2—C71.342 (6)C13—H13B0.96
N2—C61.344 (6)C13—H13A0.96
N1—C81.347 (6)C8—H80.93
C14—C151.510 (6)C6—H60.93
C14—H14B0.97C11—H11B0.96
C14—H14A0.97C11—H11A0.96
C10—C111.510 (6)C11—H11C0.96
C10—H10A0.97C3—O31.145 (5)
C10—H10B0.97O2—C21.156 (6)
C15—H15B0.96
C1—Re1—C288.49 (19)H15B—C15—H15C109.5
C1—Re1—C389.99 (19)C14—C15—H15A109.5
C2—Re1—C387.95 (19)H15B—C15—H15A109.5
C1—Re1—O4172.22 (16)H15C—C15—H15A109.5
C2—Re1—O496.95 (16)C13—C12—N3115.6 (4)
C3—Re1—O495.74 (16)C13—C12—H12B108.4
C1—Re1—N198.34 (17)N3—C12—H12B108.4
C2—Re1—N192.94 (16)C13—C12—H12A108.4
C3—Re1—N1171.64 (16)N3—C12—H12A108.4
O4—Re1—N175.91 (13)H12B—C12—H12A107.4
C1—Re1—Cl191.55 (14)C16—C17—H17B109.5
C2—Re1—Cl1178.07 (14)C16—C17—H17A109.5
C3—Re1—Cl193.98 (13)H17B—C17—H17A109.5
O4—Re1—Cl182.82 (9)C16—C17—H17C109.5
N1—Re1—Cl185.15 (10)H17B—C17—H17C109.5
N1—C5—C6120.4 (4)H17A—C17—H17C109.5
N1—C5—C4116.3 (4)O1—C1—Re1177.5 (4)
C6—C5—C4123.3 (4)N2—C7—C8122.4 (4)
C14—N3—C12109.0 (3)N2—C7—H7118.8
C14—N3—C16111.4 (3)C8—C7—H7118.8
C12—N3—C16108.3 (3)C17—C16—N3115.4 (4)
C14—N3—C10108.7 (3)C17—C16—H16A108.4
C12—N3—C10111.5 (3)N3—C16—H16A108.4
C16—N3—C10108.0 (3)C17—C16—H16B108.4
C4—O4—Re1118.2 (3)N3—C16—H16B108.4
C7—N2—C6115.8 (4)H16A—C16—H16B107.5
C8—N1—C5117.2 (4)C12—C13—H13C109.5
C8—N1—Re1128.6 (3)C12—C13—H13B109.5
C5—N1—Re1114.1 (3)H13C—C13—H13B109.5
C15—C14—N3115.6 (4)C12—C13—H13A109.5
C15—C14—H14B108.4H13C—C13—H13A109.5
N3—C14—H14B108.4H13B—C13—H13A109.5
C15—C14—H14A108.4N1—C8—C7121.1 (4)
N3—C14—H14A108.4N1—C8—H8119.4
H14B—C14—H14A107.4C7—C8—H8119.4
O5—C4—O4126.7 (4)N2—C6—C5123.1 (4)
O5—C4—C5118.0 (4)N2—C6—H6118.5
O4—C4—C5115.3 (4)C5—C6—H6118.5
C11—C10—N3115.3 (4)C10—C11—H11B109.5
C11—C10—H10A108.4C10—C11—H11A109.5
N3—C10—H10A108.4H11B—C11—H11A109.5
C11—C10—H10B108.4C10—C11—H11C109.5
N3—C10—H10B108.4H11B—C11—H11C109.5
H10A—C10—H10B107.5H11A—C11—H11C109.5
C14—C15—H15B109.5O3—C3—Re1177.0 (4)
C14—C15—H15C109.5O2—C2—Re1177.3 (4)
Acknowledgements top

The authors thank Necsa and the UFS for funding and permission to publish this work.

references
References top

Alberto, R., Schibli, R. & Schubiger, P. A. (1996). Polyhedron, 15, 1079–1083.

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19.

Alvarez, C. M., Garcia-Rodriguez, R. & Miguel, D. (2007). Dalton Trans. pp. 3546–3554.

Brandenburg, K. & Putz, H. (2005). DIAMOND. Crystal Impact GbR, Bonn, Germany.

Brasey, T., Buryak, A., Scopelliti, R. & Severin, K. (2004). Eur. J. Inorg. Chem. pp. 964–967.

Bruker (2004). SAINT-Plus, XPREP and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.

Bruker (2005). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA.

Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838.

Kemp, G. (2006). PhD thesis, University of Johannesburg, South Africa.

Mundwiler, S., Kundig, M., Ortner, K. & Alberto, R. (2004). Dalton Trans. pp. 1320–1328.

Schutte, M., Visser, H. G. & Roodt, A. (2008). Acta Cryst. E64, m1610–m1611.

Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.

Wang, W., Spingler, B. & Alberto, R. (2003). Inorg. Chim. Acta. 355, 386–391.