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

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

aRadiochemistry, South African Nuclear Energy Corporation Ltd. (Necsa), PO Box 582, Pretoria, 0001, South Africa, and bDepartment of Chemistry, University of the Free State, PO Box 339, Bloemfontein, 9300, South Africa
*Correspondence e-mail: visserhg.sci@mail.uovs.ac.za

(Received 12 October 2009; accepted 14 October 2009; online 17 October 2009)

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.

Related literature

For synthetic background, see: Alberto et al. (1996[Alberto, R., Schibli, R. & Schubiger, P. A. (1996). Polyhedron, 15, 1079-1083.]). For related structures, see: Schutte et al. (2008[Schutte, M., Visser, H. G. & Roodt, A. (2008). Acta Cryst. E64, m1610-m1611.]); Kemp (2006[Kemp, G. (2006). PhD thesis, University of Johannesburg, South Africa.]); Wang et al. (2003[Wang, W., Spingler, B. & Alberto, R. (2003). Inorg. Chim. Acta. 355, 386-391.]); Alvarez et al. (2007[Alvarez, C. M., Garcia-Rodriguez, R. & Miguel, D. (2007). Dalton Trans. pp. 3546-3554.]); Brasey et al. (2004[Brasey, T., Buryak, A., Scopelliti, R. & Severin, K. (2004). Eur. J. Inorg. Chem. pp. 964-967.]); Mundwiler et al. (2004[Mundwiler, S., Kundig, M., Ortner, K. & Alberto, R. (2004). Dalton Trans. pp. 1320-1328.]). For bond-length data, see: Allen et al. (1987[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.]).

[Scheme 1]

Experimental

Crystal data
  • (C8H20N)[Re(C5H3N2O2)Cl(CO)3]

  • Mr = 559.02

  • Monoclinic, P 21 /c

  • a = 7.927 (5) Å

  • b = 22.278 (5) Å

  • c = 10.903 (5) Å

  • β = 90.506 (5)°

  • V = 1925.4 (16) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 6.48 mm−1

  • T = 100 K

  • 0.27 × 0.20 × 0.11 mm

Data collection
  • Bruker X8 APEXII 4K Kappa CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2004[Bruker (2004). SAINT-Plus, XPREP and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.273, Tmax = 0.539

  • 32482 measured reflections

  • 4781 independent reflections

  • 4121 reflections with I > 2σ(I)

  • Rint = 0.046

Refinement
  • R[F2 > 2σ(F2)] = 0.021

  • wR(F2) = 0.098

  • S = 1.18

  • 4781 reflections

  • 235 parameters

  • H-atom parameters constrained

  • Δρmax = 1.05 e Å−3

  • Δρmin = −1.38 e Å−3

Data collection: APEX2 (Bruker, 2005[Bruker (2005). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT-Plus (Bruker, 2004[Bruker (2004). SAINT-Plus, XPREP and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT-Plus and XPREP (Bruker, 2004[Bruker (2004). SAINT-Plus, XPREP and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); 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: WinGX (Farrugia, 1999[Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.]).

Supporting information


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.

Structure description 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.

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).

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 m3
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 mm1
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)
Graphite monochromatorRint = 0.046
phi and ω scansθmax = 28.3°, θmin = 1.8°
Absorption correction: multi-scan
(SADABS; Bruker, 2004)
h = 109
Tmin = 0.273, Tmax = 0.539k = 2929
32482 measured reflectionsl = 1413
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 Å3
4781 reflectionsΔρmin = 1.38 e Å3
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 mm1
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 reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0210 restraints
wR(F2) = 0.098H-atom parameters constrained
S = 1.18Δρmax = 1.05 e Å3
4781 reflectionsΔρmin = 1.38 e Å3
235 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.

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)
H14B0.15680.00470.16660.018*
H14A0.14030.0640.09060.018*
C40.1762 (5)0.1323 (2)0.1880 (4)0.0131 (9)
C100.1294 (6)0.0471 (2)0.3912 (4)0.0169 (9)
H10A0.16670.00580.38490.02*
H10B0.00750.04670.39830.02*
C150.0836 (6)0.0368 (2)0.1619 (4)0.0182 (10)
H15B0.11530.01380.09090.027*
H15C0.11970.01640.23450.027*
H15A0.13610.07560.15780.027*
C120.3647 (5)0.0855 (2)0.2602 (4)0.0147 (9)
H12B0.40690.11060.32640.018*
H12A0.38750.10620.18380.018*
C170.1141 (6)0.1786 (2)0.1620 (5)0.0215 (10)
H17B0.06370.21730.17390.032*
H17A0.2310.18350.14180.032*
H17C0.05690.15810.09620.032*
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)
H16A0.15450.16410.34450.017*
H16B0.01880.13860.29880.017*
C130.4627 (6)0.0272 (2)0.2612 (5)0.0228 (11)
H13C0.58080.03550.25250.034*
H13B0.44440.00670.33740.034*
H13A0.4250.00230.19450.034*
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)
H11B0.16770.05040.57650.034*
H11A0.32410.07330.50280.034*
H11C0.16460.11430.51620.034*
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, º) 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)

Experimental details

Crystal data
Chemical formula(C8H20N)[Re(C5H3N2O2)Cl(CO)3]
Mr559.02
Crystal system, space groupMonoclinic, P21/c
Temperature (K)100
a, b, c (Å)7.927 (5), 22.278 (5), 10.903 (5)
β (°) 90.506 (5)
V3)1925.4 (16)
Z4
Radiation typeMo Kα
µ (mm1)6.48
Crystal size (mm)0.27 × 0.20 × 0.11
Data collection
DiffractometerBruker X8 APEXII 4K Kappa CCD
Absorption correctionMulti-scan
(SADABS; Bruker, 2004)
Tmin, Tmax0.273, 0.539
No. of measured, independent and
observed [I > 2σ(I)] reflections
32482, 4781, 4121
Rint0.046
(sin θ/λ)max1)0.667
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.021, 0.098, 1.18
No. of reflections4781
No. of parameters235
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)1.05, 1.38

Computer programs: APEX2 (Bruker, 2005), SAINT-Plus (Bruker, 2004), SAINT-Plus and XPREP (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), DIAMOND (Brandenburg & Putz, 2005), WinGX (Farrugia, 1999).

 

Acknowledgements

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

References

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