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Acta Crystallogr Sect E Struct Rep Online. 2010 August 1; 66(Pt 8): m1042–m1043.
Published online 2010 July 31. doi:  10.1107/S160053681002893X
PMCID: PMC3007518

Tetra­ethyl­ammonium tricarbonyl­chlorido(quinoxaline-2-carboxyl­ato-κ2 N 1,O)rhenate(I)

Abstract

In the title compound, (C8H20N)[Re(C9H5N2O2)Cl(CO)3], the ReI atom is coordinated facially by three carbonyl groups, the bidentate quinoxaline-2-carbaldehyde ligand and a chloride atom, forming a distorted octahedral geometry.. The crystal packing is controlled by C—H(...)O hydrogen bonding and π–π stacking inter­actions involving the benzene rings, with a centroid–centroid distance of 3.4220 (1) Å.

Related literature

For synthetic background, see: Alberto et al. (1996 [triangle]). For related structures, see: Schutte et al. (2008 [triangle]); Wang et al. (2003 [triangle]); Alvarez et al. (2007 [triangle]); Brasey et al. (2004 [triangle]); Mundwiler et al. (2004 [triangle]); Feng et al. (2007 [triangle]); Suthiram et al. (2009 [triangle]). For bond-length data, see: Allen et al. (1987 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-m1042-scheme1.jpg

Experimental

Crystal data

  • (C8H20N)[Re(C9H5N2O2)Cl(CO)3]
  • M r = 609.08
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-m1042-efi1.jpg
  • a = 8.402 (5) Å
  • b = 10.077 (5) Å
  • c = 13.495 (5) Å
  • α = 97.433 (5)°
  • β = 103.141 (5)°
  • γ = 90.686 (5)°
  • V = 1102.3 (9) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 5.67 mm−1
  • T = 100 K
  • 0.33 × 0.29 × 0.20 mm

Data collection

  • Bruker X8 APEXII 4K Kappa CCD diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2004 [triangle]) T min = 0.169, T max = 0.324
  • 22501 measured reflections
  • 5458 independent reflections
  • 4988 reflections with I > 2σ(I)
  • R int = 0.054

Refinement

  • R[F 2 > 2σ(F 2)] = 0.027
  • wR(F 2) = 0.065
  • S = 1.07
  • 5458 reflections
  • 275 parameters
  • 12 restraints
  • H-atom parameters constrained
  • Δρmax = 1.74 e Å−3
  • Δρmin = −1.04 e Å−3

Data collection: APEX2 (Bruker, 2005 [triangle]); cell refinement: SAINT-Plus (Bruker, 2004 [triangle]); data reduction: SAINT-Plus and XPREP (Bruker, 2004 [triangle]); program(s) used to solve structure: SIR97 (Altomare et al., 1999 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: DIAMOND (Brandenburg & Putz, 2005 [triangle]); software used to prepare material for publication: WinGX (Farrugia, 1999 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053681002893X/pv2307sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053681002893X/pv2307Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

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

supplementary crystallographic information

Comment

The title complex, (C8H20N)[Re(C9H5N2O2)Cl(CO)3], forms a part of an ongoing investigation of the structural and kinetic behaviour of fac-Re(CO)3 compounds (Schutte et al., (2008); Wang et al., (2003); Alvarez et al., (2007); Brasey et al., (2004); Suthiram et al., (2009)). 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 of 74.71 (11) ° might be a reason for the distorted octahedral geometry around the metal centre. The crystal packing is controlled by C—H···O hydrogen bonding and π - π -stacking interactions involving the benzene rings, with a centroid-centroid distance of 3.4220 (1) Å (Fig. 2).

Experimental

[NEt4]2[Re(CO)3Cl3] (150 mg, 0.235 mmol) was added to 30 ml me thanol to result in a suspension which was heated for a few minutes until the solution turned clear. Quinoxaline-2-carbaldehyde (41 mg, 0.235 mmol) was dissolved in 5 ml me thanol and slowly added to the reaction solution whilst stirring. K2CO3 (16.6 mg, 0.120 mmol) was added to the solution. The dark orange solution that formed was refluxed for 4 h after which the solvent was evaporated completely on a rotoevaporator. The resulting solid was redissolved in a minimum volume of dichloromethane, layered with diethyl ether and left to stand in a refrigerator. After several days red crystals suitable for X-ray diffraction were isolated. (Yield: 56 mg, 39%).

Refinement

The methyl, methylene and aromatic H atoms were placed in geometrically idealized positions with C—H = 0.96, 0.97 and 0.93 Å, respectively and constrained to ride on their parent atoms, with Uiso(H) = 1.5Ueq(methyl C) and 1.2Ueq(non-methyl C). The highest residual electron-density peak was located 0.85 Å from Re1 and the deepest hole was located 0.87 Å from Re1.

Figures

Fig. 1.
Molecular structure of the title compound. Displacement ellipsoids are drawn at the 50% probability displacement level.
Fig. 2.
π-π -Stacking interactions of the title compound; cations have been omitted for clarity.

Crystal data

(C8H20N)[Re(C9H5N2O2)Cl(CO)3]Z = 2
Mr = 609.08F(000) = 596
Triclinic, P1Dx = 1.835 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71069 Å
a = 8.402 (5) ÅCell parameters from 9175 reflections
b = 10.077 (5) Åθ = 2.7–28.3°
c = 13.495 (5) ŵ = 5.67 mm1
α = 97.433 (5)°T = 100 K
β = 103.141 (5)°Cuboid, red
γ = 90.686 (5)°0.33 × 0.29 × 0.20 mm
V = 1102.3 (9) Å3

Data collection

Bruker X8 APEXII 4K Kappa CCD diffractometer5458 independent reflections
Radiation source: sealed tube4988 reflections with I > 2σ(I)
graphiteRint = 0.054
[var phi] & ω scansθmax = 28.3°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2004)h = −11→10
Tmin = 0.169, Tmax = 0.324k = −13→13
22501 measured reflectionsl = −17→17

Refinement

Refinement on F212 restraints
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.027w = 1/[σ2(Fo2) + (0.0211P)2 + 1.8438P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.065(Δ/σ)max = 0.003
S = 1.07Δρmax = 1.74 e Å3
5458 reflectionsΔρmin = −1.04 e Å3
275 parameters

Special details

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)

xyzUiso*/Ueq
Re10.528310 (18)0.255408 (14)0.783120 (11)0.01364 (5)
Cl10.81842 (12)0.20551 (10)0.85067 (7)0.0205 (2)
O30.1770 (4)0.3314 (3)0.6974 (2)0.0304 (7)
C30.3080 (5)0.3001 (4)0.7268 (3)0.0208 (8)
N30.0788 (4)0.7963 (3)0.8126 (2)0.0139 (6)
O10.4040 (4)0.1531 (3)0.9570 (2)0.0279 (7)
O40.5167 (3)0.0596 (3)0.6987 (2)0.0182 (6)
N10.6229 (4)0.2820 (3)0.6466 (2)0.0124 (6)
O20.5953 (4)0.5310 (3)0.9133 (2)0.0290 (7)
C20.5683 (5)0.4271 (4)0.8632 (3)0.0191 (8)
C13−0.0041 (5)0.8729 (4)0.8902 (3)0.0162 (8)
H13A0.04180.84690.95720.019*
H13B0.02180.96770.8940.019*
C150.0262 (5)0.6478 (4)0.7929 (3)0.0198 (8)
H15A−0.0910.63960.76470.024*
H15B0.07840.60370.74110.024*
C10.4532 (5)0.1938 (4)0.8923 (3)0.0195 (8)
C200.0905 (5)0.9922 (4)0.7091 (3)0.0236 (9)
H20A0.05511.05110.76090.035*
H20B0.04661.01930.6430.035*
H20C0.20780.99630.72290.035*
C14−0.1876 (5)0.8518 (4)0.8673 (3)0.0214 (8)
H14A−0.23420.87030.7990.032*
H14B−0.23050.9110.91560.032*
H14C−0.21480.76070.87290.032*
C180.3657 (5)0.7536 (5)0.7873 (4)0.0311 (10)
H18A0.33620.660.76790.047*
H18B0.47890.76450.82270.047*
H18C0.34860.79740.72690.047*
C190.0298 (5)0.8491 (4)0.7098 (3)0.0160 (8)
H19A−0.08860.84440.68820.019*
H19B0.0710.79030.65940.019*
C160.0657 (6)0.5747 (4)0.8857 (4)0.0296 (10)
H16A0.18220.57160.9090.044*
H16B0.01850.48520.86770.044*
H16C0.02150.6210.93950.044*
C170.2609 (5)0.8150 (4)0.8572 (3)0.0207 (8)
H17A0.28720.77610.92070.025*
H17B0.28890.91020.8740.025*
O50.6377 (4)−0.0666 (3)0.5901 (2)0.0236 (6)
N20.7964 (4)0.2711 (3)0.4892 (3)0.0185 (7)
C120.6622 (4)0.3988 (3)0.6110 (3)0.0116 (7)
C100.6387 (5)0.6348 (4)0.6071 (3)0.0155 (7)
H100.59790.7160.6290.019*
C110.6071 (4)0.5229 (4)0.6470 (3)0.0141 (7)
H110.54890.52850.69830.017*
C50.6598 (5)0.1677 (4)0.5993 (3)0.0143 (7)
C60.7465 (5)0.1632 (4)0.5210 (3)0.0184 (8)
H60.76960.07990.49020.022*
C70.7515 (4)0.3910 (4)0.5336 (3)0.0139 (7)
C40.6025 (5)0.0410 (4)0.6313 (3)0.0167 (8)
C80.7889 (5)0.5102 (4)0.4965 (3)0.0159 (7)
H80.85150.50730.44770.019*
C90.7334 (4)0.6286 (4)0.5322 (3)0.0163 (8)
H90.75770.70640.50730.02*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Re10.01848 (8)0.01209 (8)0.01132 (8)−0.00015 (5)0.00457 (6)0.00329 (5)
Cl10.0230 (5)0.0222 (5)0.0152 (5)0.0047 (4)0.0008 (4)0.0037 (4)
O30.0226 (16)0.0426 (19)0.0309 (18)0.0056 (14)0.0086 (14)0.0175 (15)
C30.029 (2)0.024 (2)0.012 (2)−0.0069 (17)0.0097 (17)0.0064 (16)
N30.0119 (15)0.0165 (15)0.0126 (16)0.0013 (12)0.0022 (12)0.0002 (12)
O10.0362 (18)0.0315 (17)0.0191 (16)−0.0072 (14)0.0108 (13)0.0076 (13)
O40.0267 (15)0.0127 (12)0.0158 (14)−0.0025 (11)0.0051 (12)0.0044 (10)
N10.0110 (14)0.0142 (14)0.0113 (16)−0.0001 (11)0.0009 (12)0.0025 (12)
O20.049 (2)0.0187 (15)0.0196 (16)0.0003 (14)0.0098 (14)−0.0005 (12)
C20.025 (2)0.023 (2)0.0120 (19)0.0013 (16)0.0061 (16)0.0083 (16)
C130.0191 (19)0.0191 (18)0.0112 (19)0.0039 (15)0.0058 (15)0.0009 (14)
C150.022 (2)0.0164 (18)0.018 (2)−0.0023 (15)0.0019 (16)−0.0025 (15)
C10.021 (2)0.0199 (19)0.017 (2)−0.0021 (15)0.0020 (16)0.0022 (15)
C200.028 (2)0.024 (2)0.021 (2)0.0015 (17)0.0094 (18)0.0061 (17)
C140.020 (2)0.024 (2)0.023 (2)0.0041 (16)0.0096 (17)0.0043 (17)
C180.019 (2)0.041 (3)0.032 (3)0.0088 (19)0.0047 (19)0.003 (2)
C190.0155 (18)0.0215 (19)0.0111 (19)0.0023 (15)0.0031 (14)0.0023 (15)
C160.040 (3)0.019 (2)0.027 (2)−0.0015 (18)0.000 (2)0.0060 (18)
C170.0113 (18)0.028 (2)0.019 (2)−0.0025 (15)−0.0029 (15)0.0030 (17)
O50.0395 (18)0.0115 (13)0.0188 (15)0.0045 (12)0.0046 (13)0.0015 (11)
N20.0205 (17)0.0208 (16)0.0154 (17)0.0051 (13)0.0069 (13)0.0020 (13)
C120.0146 (17)0.0127 (16)0.0062 (17)−0.0021 (13)−0.0012 (13)0.0028 (13)
C100.0173 (18)0.0115 (16)0.0144 (19)−0.0003 (14)−0.0027 (15)0.0011 (14)
C110.0140 (17)0.0175 (17)0.0093 (18)0.0012 (14)−0.0004 (14)0.0019 (14)
C50.0169 (18)0.0162 (17)0.0080 (18)0.0031 (14)−0.0016 (14)0.0025 (14)
C60.023 (2)0.0172 (18)0.015 (2)0.0064 (15)0.0056 (16)0.0002 (15)
C70.0134 (17)0.0166 (17)0.0106 (18)0.0023 (14)0.0003 (14)0.0026 (14)
C40.022 (2)0.0128 (17)0.0136 (19)0.0011 (14)−0.0012 (15)0.0040 (14)
C80.0151 (18)0.0208 (18)0.0115 (19)−0.0007 (14)−0.0005 (14)0.0071 (15)
C90.0154 (18)0.0160 (17)0.016 (2)−0.0038 (14)−0.0023 (15)0.0059 (14)

Geometric parameters (Å, °)

Re1—C11.899 (4)C14—H14C0.96
Re1—C21.900 (4)C18—C171.513 (6)
Re1—C31.917 (5)C18—H18A0.96
Re1—O42.136 (3)C18—H18B0.96
Re1—N12.211 (3)C18—H18C0.96
Re1—Cl12.4825 (16)C19—H19A0.97
O3—C31.145 (5)C19—H19B0.97
N3—C171.511 (5)C16—H16A0.96
N3—C191.521 (5)C16—H16B0.96
N3—C131.521 (5)C16—H16C0.96
N3—C151.527 (5)C17—H17A0.97
O1—C11.164 (5)C17—H17B0.97
O4—C41.281 (5)O5—C41.225 (4)
N1—C51.319 (5)N2—C61.315 (5)
N1—C121.390 (4)N2—C71.374 (5)
O2—C21.160 (5)C12—C111.405 (5)
C13—C141.508 (5)C12—C71.413 (5)
C13—H13A0.97C10—C111.360 (5)
C13—H13B0.97C10—C91.417 (5)
C15—C161.510 (6)C10—H100.93
C15—H15A0.97C11—H110.93
C15—H15B0.97C5—C61.410 (5)
C20—C191.526 (5)C5—C41.506 (5)
C20—H20A0.96C6—H60.93
C20—H20B0.96C7—C81.417 (5)
C20—H20C0.96C8—C91.356 (5)
C14—H14A0.96C8—H80.93
C14—H14B0.96C9—H90.93
C1—Re1—C288.06 (17)C17—C18—H18A109.5
C1—Re1—C388.08 (17)C17—C18—H18B109.5
C2—Re1—C390.12 (17)H18A—C18—H18B109.5
C1—Re1—O493.58 (14)C17—C18—H18C109.5
C2—Re1—O4172.60 (14)H18A—C18—H18C109.5
C3—Re1—O497.15 (15)H18B—C18—H18C109.5
C1—Re1—N1167.94 (14)N3—C19—C20115.4 (3)
C2—Re1—N1103.18 (14)N3—C19—H19A108.4
C3—Re1—N196.14 (14)C20—C19—H19A108.4
O4—Re1—N174.71 (11)N3—C19—H19B108.4
C1—Re1—Cl194.68 (13)C20—C19—H19B108.4
C2—Re1—Cl188.98 (13)H19A—C19—H19B107.5
C3—Re1—Cl1177.06 (11)C15—C16—H16A109.5
O4—Re1—Cl183.70 (8)C15—C16—H16B109.5
N1—Re1—Cl181.35 (8)H16A—C16—H16B109.5
O3—C3—Re1176.6 (4)C15—C16—H16C109.5
C17—N3—C19111.5 (3)H16A—C16—H16C109.5
C17—N3—C13106.6 (3)H16B—C16—H16C109.5
C19—N3—C13110.3 (3)N3—C17—C18114.5 (3)
C17—N3—C15110.7 (3)N3—C17—H17A108.6
C19—N3—C15106.6 (3)C18—C17—H17A108.6
C13—N3—C15111.2 (3)N3—C17—H17B108.6
C4—O4—Re1117.4 (2)C18—C17—H17B108.6
C5—N1—C12117.2 (3)H17A—C17—H17B107.6
C5—N1—Re1112.5 (2)C6—N2—C7115.9 (3)
C12—N1—Re1129.9 (2)N1—C12—C11120.9 (3)
O2—C2—Re1178.7 (4)N1—C12—C7119.3 (3)
C14—C13—N3115.2 (3)C11—C12—C7119.7 (3)
C14—C13—H13A108.5C11—C10—C9120.4 (3)
N3—C13—H13A108.5C11—C10—H10119.8
C14—C13—H13B108.5C9—C10—H10119.8
N3—C13—H13B108.5C10—C11—C12120.1 (4)
H13A—C13—H13B107.5C10—C11—H11120
C16—C15—N3115.3 (3)C12—C11—H11120
C16—C15—H15A108.4N1—C5—C6121.8 (3)
N3—C15—H15A108.4N1—C5—C4117.0 (3)
C16—C15—H15B108.4C6—C5—C4121.1 (3)
N3—C15—H15B108.4N2—C6—C5123.3 (3)
H15A—C15—H15B107.5N2—C6—H6118.4
O1—C1—Re1177.9 (4)C5—C6—H6118.4
C19—C20—H20A109.5N2—C7—C12122.2 (3)
C19—C20—H20B109.5N2—C7—C8118.7 (3)
H20A—C20—H20B109.5C12—C7—C8119.0 (3)
C19—C20—H20C109.5O5—C4—O4127.0 (4)
H20A—C20—H20C109.5O5—C4—C5118.5 (4)
H20B—C20—H20C109.5O4—C4—C5114.5 (3)
C13—C14—H14A109.5C9—C8—C7120.1 (4)
C13—C14—H14B109.5C9—C8—H8120
H14A—C14—H14B109.5C7—C8—H8120
C13—C14—H14C109.5C8—C9—C10120.6 (3)
H14A—C14—H14C109.5C8—C9—H9119.7
H14B—C14—H14C109.5C10—C9—H9119.7
C1—Re1—O4—C4−159.2 (3)C15—N3—C19—C20−172.6 (3)
C3—Re1—O4—C4112.3 (3)C19—N3—C17—C18−55.5 (4)
Cl1—Re1—O4—C4−64.9 (3)C13—N3—C17—C18−176.0 (3)
C2—Re1—N1—C5157.7 (3)C15—N3—C17—C1863.0 (4)
C3—Re1—N1—C5−110.7 (3)C5—N1—C12—C11171.0 (3)
Cl1—Re1—N1—C570.8 (2)Re1—N1—C12—C7167.3 (2)
C1—Re1—N1—C12−174.0 (6)N1—C12—C11—C10−176.3 (3)
C3—Re1—N1—C1276.0 (3)Re1—N1—C5—C6−169.4 (3)
O4—Re1—N1—C12171.8 (3)C12—N1—C5—C4−174.2 (3)
Cl1—Re1—N1—C12−102.4 (3)Re1—N1—C5—C411.5 (4)
C17—N3—C13—C14−172.0 (3)C4—C5—C6—N2178.8 (4)
C19—N3—C13—C1466.8 (4)C6—N2—C7—C8−174.6 (3)
C15—N3—C13—C14−51.2 (4)C11—C12—C7—N2−174.3 (3)
C17—N3—C15—C1657.8 (5)N1—C12—C7—C8179.0 (3)
C19—N3—C15—C16179.3 (3)Re1—O4—C4—O5164.6 (3)
C13—N3—C15—C16−60.5 (4)N1—C5—C4—O5−178.6 (3)
C17—N3—C19—C20−51.7 (4)C6—C5—C4—O4−175.9 (3)
C13—N3—C19—C2066.6 (4)N2—C7—C8—C9174.1 (3)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C10—H10···O5i0.932.353.046 (5)131

Symmetry codes: (i) x, y+1, z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: PV2307).

References

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