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Acta Crystallogr Sect E Struct Rep Online. 2008 October 1; 64(Pt 10): m1226–m1227.
Published online 2008 September 6. doi:  10.1107/S160053680802761X
PMCID: PMC2959348

Aqua­tricarbon­yl(4-carboxy­pyridine-2-carboxyl­ato-κ2 N,O 2)rhenium(I)

Abstract

There are two mol­ecules with similar bond dimensions in the asymmetric unit of the title complex, [Re(C7H4NO4)(CO)3(H2O)]. The metal centre is coordinated facially by three carbonyl groups, is chelated by a 4-carboxy­pyridine-2-carboxyl­ate ligand and is also coordinated by a water mol­ecule. O—H(...)O hydrogen bonds give rise to a three-dimensional network.

Related literature

For the monoclinic polymorph of the title compound, see: Mundwiler et al. (2004 [triangle]). For related structures, see: Kemp (2006 [triangle]); Roodt et al. (2003 [triangle]); Schutte et al. (2007 [triangle]); Wang et al. (2003 [triangle]); Alvarez et al. (2007 [triangle]). For the synthesis of the precursor, see: Alberto et al. (1996 [triangle]);

An external file that holds a picture, illustration, etc.
Object name is e-64-m1226-scheme1.jpg

Experimental

Crystal data

  • [Re(C7H4NO4)(CO)3(H2O)]
  • M r = 454.37
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-m1226-efi1.jpg
  • a = 9.5024 (11) Å
  • b = 12.4254 (16) Å
  • c = 12.4889 (16) Å
  • α = 101.799 (4)°
  • β = 107.943 (4)°
  • γ = 111.346 (4)°
  • V = 1220.4 (3) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 10.00 mm−1
  • T = 100 (2) K
  • 0.27 × 0.17 × 0.05 mm

Data collection

  • Bruker APEXII diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2004 [triangle]) T min = 0.140, T max = 0.605
  • 15096 measured reflections
  • 5848 independent reflections
  • 4869 reflections with I > 2σ(I)
  • R int = 0.037

Refinement

  • R[F 2 > 2σ(F 2)] = 0.026
  • wR(F 2) = 0.065
  • S = 1.05
  • 5848 reflections
  • 373 parameters
  • 7 restraints
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 1.21 e Å−3
  • Δρmin = −1.80 e Å−3

Data collection: APEX2 (Bruker, 2005 [triangle]); cell refinement: SAINT-Plus (Bruker, 2004 [triangle]); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: DIAMOND (Brandenberg & Putz, 2005 [triangle]) and ORTEP-3 (Farrugia, 1999 [triangle]); software used to prepare material for publication: SHELXL97.

Table 1
Selected geometric parameters (Å, °)
Table 2
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053680802761X/ng2479sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680802761X/ng2479Isup2.hkl

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

Acknowledgments

The University of the Free State and Professor A. Roodt are gratefully aknowledged for financial support. Dr A.J. Muller is kindly acknowledged for the data collection.

supplementary crystallographic information

Comment

The title compound, Re(C10H6NO8),is one of many Re(I)-tricarbonyl complexes currently under investigation in the field of radiopharmacology. One polymorph of the title compound was reported earlier [Mundwiler et al., (2004)].

The Re(I) core is coordinated by three facial carbonyl groups, one pyridine-2-carboxylato-4-carboxylic acid ligand and a water molecule. A slightly distorted octahedral geometry around the Re(I) metal centre is observed, possibly due to the effect of the small bite angles of 74.78 (14)° and 74.98 (12)° respectively for the two pyridine-2,4-dicarboxylic acid units. The Re—OH2 bond distances of 2.153 (4) Å and 2.170 (4) Å compare well with related structures [Mundwiler et al., (2004) and Kemp, (2006)] of 2.198 (5) Å and 2.192 (4) Å. The Re—CO distances are well within the normal range, 1.883 (6) Å to 1.947 (6) Å. The crystal structure shows a range of hydrogen bonding of the types OH—O and CH—O thereby forming a 3D polymeric network, with DA distances ranging from 2.595 (4) Å to 3.426 (5) Å.

Experimental

[NEt4]2[Re(CO)3Br3] (300 mg, 0.389 mmol), as prepared by Alberto et al. (1996) was stirred in 40 ml of water at pH 2.2 for 20 minutes until dissolved. AgNO3 (198 mg, 1.167 mmol) was added to the solution and stirred for 24 h at room temperature. The precipitate, AgBr, was filtered off and weighed(0.220 g). 2,4-Pyridinedicarboxylic acid (65 mg, 0.389 mmol) was added to the filtrate as a solid and stirred for 36 h. The solution turned bright yellow with a light yellow precipitate. The product was filtered off, dried and weighed. Crystals were obtained by slow evaporation of the filtrate. (Yield: 0.240 g, 68%).

Refinement

The aromatic H atoms were placed in geometrically idealized positions and constrained to ride on its parent atoms with U<i/>iso(H) = 1.2U<i/>eq(C). The highest electron density lies within 1.14 Å from Re1. The hydrogen atoms of the coordinated water molecules were determined from a difference Fourier map and their positional parameters freely refined with U<i/>iso(H) = 1.5U<i/>eq(O).

Figures

Fig. 1.
Representation of the title compound, showing the numbering scheme and displacement ellipsoids (50% probability).

Crystal data

[Re(C7H4NO4)(CO)3(H2O)]Z = 4
Mr = 454.37F(000) = 848.0
Triclinic, P1Dx = 2.473 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 9.5024 (11) ÅCell parameters from 7140 reflections
b = 12.4254 (16) Åθ = 2.8–28.3°
c = 12.4889 (16) ŵ = 10.00 mm1
α = 101.799 (4)°T = 100 K
β = 107.943 (4)°Plate, yellow
γ = 111.346 (4)°0.27 × 0.17 × 0.05 mm
V = 1220.4 (3) Å3

Data collection

Bruker APEX diffractometer4869 reflections with I > 2σ(I)
[var phi] and ω scansRint = 0.037
Absorption correction: multi-scan (SADABS; Bruker, 2004)θmax = 28.3°, θmin = 1.8°
Tmin = 0.140, Tmax = 0.605h = −12→12
15096 measured reflectionsk = −16→15
5048 independent reflectionsl = −16→16

Refinement

Refinement on F27 restraints
Least-squares matrix: fullH atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.027w = 1/[σ2(Fo2) + (0.0251P)2] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.065(Δ/σ)max = 0.015
S = 1.05Δρmax = 1.21 e Å3
5848 reflectionsΔρmin = −1.80 e Å3
373 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
N10.3078 (4)0.2654 (3)0.5400 (3)0.0095 (8)
O50.1030 (4)0.1933 (3)0.3130 (2)0.0113 (7)
O60.2391 (4)0.1072 (3)0.2433 (3)0.0152 (7)
C40.2193 (6)0.1635 (4)0.3289 (4)0.0116 (9)
O150.0841 (4)0.2152 (3)−0.1450 (3)0.0112 (7)
C50.3392 (6)0.1998 (4)0.4572 (4)0.0102 (9)
O160.0735 (4)0.0827 (3)−0.3002 (3)0.0160 (7)
C150.3019 (5)0.1585 (4)−0.1099 (4)0.0097 (9)
C140.1407 (6)0.1487 (4)−0.1934 (4)0.0118 (10)
C180.5968 (5)0.1949 (4)0.0518 (4)0.0116 (9)
H180.69810.20890.10840.014*
C170.5336 (6)0.1168 (4)−0.0662 (4)0.0115 (9)
C160.3816 (5)0.0981 (4)−0.1491 (4)0.0106 (9)
H160.33580.0459−0.22880.013*
C80.5409 (6)0.2756 (4)0.6944 (4)0.0127 (10)
H80.60810.30190.77610.015*
C60.4696 (6)0.1716 (4)0.4875 (4)0.0129 (10)
H60.48840.12780.42820.015*
C90.4082 (5)0.3013 (4)0.6568 (4)0.0122 (10)
H90.38740.34530.71460.015*
C70.5727 (5)0.2098 (4)0.6085 (4)0.0105 (9)
C200.6310 (6)0.0551 (4)−0.0994 (4)0.0131 (10)
C190.5084 (5)0.2516 (4)0.0845 (4)0.0118 (10)
H190.55070.30310.16410.014*
N20.3633 (4)0.2346 (3)0.0051 (3)0.0092 (8)
O80.7441 (4)0.1233 (3)0.5666 (3)0.0200 (8)
O70.8100 (4)0.2290 (3)0.7589 (3)0.0190 (8)
H70.88780.21180.7730.029*
C100.7178 (5)0.1827 (4)0.6423 (4)0.0134 (10)
O180.7570 (4)0.0669 (3)−0.0231 (3)0.0174 (8)
O170.5674 (4)−0.0113 (3)−0.2139 (3)0.0176 (8)
H170.6264−0.0424−0.22580.026*
O110.4169 (4)0.4220 (3)0.3181 (3)0.0206 (8)
O12−0.0486 (5)0.3985 (3)0.0753 (3)0.0290 (9)
C110.3339 (6)0.3833 (4)0.2154 (4)0.0129 (10)
C120.0473 (6)0.3683 (4)0.0652 (4)0.0165 (10)
O2−0.2361 (5)0.3030 (4)0.3410 (3)0.0296 (10)
C2−0.1119 (6)0.3005 (4)0.3895 (4)0.0178 (11)
C30.2069 (6)0.4532 (5)0.4629 (4)0.0211 (12)
O30.2698 (5)0.5484 (3)0.4535 (3)0.0283 (9)
C130.3283 (6)0.4712 (5)0.0407 (4)0.0162 (10)
O130.4026 (4)0.5690 (3)0.0395 (3)0.0209 (8)
O140.0791 (4)0.1290 (3)0.0380 (3)0.0128 (7)
O4−0.0362 (4)0.1106 (3)0.4661 (3)0.0191 (8)
H4A−0.070 (6)0.046 (3)0.408 (3)0.029*
H4B−0.092 (6)0.097 (4)0.508 (4)0.029*
H14B0.123 (5)0.112 (5)0.098 (3)0.029*
H14A−0.025 (2)0.093 (4)0.010 (4)0.029*
Re20.20999 (2)0.315032 (16)0.046124 (15)0.00973 (6)
Re10.09158 (2)0.296297 (16)0.468442 (15)0.01020 (6)
C10.1002 (6)0.3789 (5)0.6194 (4)0.0165 (10)
O10.1138 (5)0.4303 (3)0.7126 (3)0.0272 (9)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
N10.0096 (18)0.013 (2)0.0088 (18)0.0082 (16)0.0031 (15)0.0057 (16)
O50.0128 (16)0.0157 (18)0.0070 (15)0.0087 (14)0.0052 (13)0.0014 (13)
O60.0183 (17)0.0185 (19)0.0109 (16)0.0125 (15)0.0057 (14)0.0022 (14)
C40.016 (2)0.013 (2)0.013 (2)0.010 (2)0.0097 (19)0.0047 (19)
O150.0142 (16)0.0144 (17)0.0063 (14)0.0101 (14)0.0035 (13)0.0007 (13)
C50.012 (2)0.008 (2)0.006 (2)0.0038 (18)0.0014 (17)−0.0007 (17)
O160.0185 (18)0.0204 (19)0.0076 (15)0.0131 (15)0.0024 (13)−0.0010 (14)
C150.012 (2)0.008 (2)0.009 (2)0.0047 (18)0.0040 (18)0.0034 (18)
C140.012 (2)0.016 (3)0.010 (2)0.008 (2)0.0044 (18)0.0060 (19)
C180.006 (2)0.017 (3)0.009 (2)0.0058 (19)0.0008 (17)0.0032 (19)
C170.015 (2)0.011 (2)0.014 (2)0.0092 (19)0.0085 (19)0.0059 (19)
C160.011 (2)0.010 (2)0.008 (2)0.0039 (19)0.0039 (17)0.0016 (18)
C80.012 (2)0.016 (2)0.006 (2)0.006 (2)0.0017 (17)0.0023 (18)
C60.013 (2)0.010 (2)0.013 (2)0.0028 (19)0.0073 (19)0.0026 (19)
C90.013 (2)0.015 (2)0.006 (2)0.008 (2)0.0025 (18)−0.0010 (18)
C70.005 (2)0.014 (2)0.011 (2)0.0053 (18)0.0015 (17)0.0029 (19)
C200.012 (2)0.014 (2)0.016 (2)0.008 (2)0.0073 (19)0.005 (2)
C190.010 (2)0.014 (2)0.008 (2)0.0056 (19)0.0030 (18)0.0001 (18)
N20.0081 (18)0.010 (2)0.0085 (18)0.0053 (16)0.0021 (14)0.0014 (15)
O80.0175 (18)0.027 (2)0.0152 (17)0.0143 (16)0.0046 (14)0.0022 (15)
O70.0150 (17)0.029 (2)0.0117 (16)0.0145 (16)0.0008 (14)0.0025 (15)
C100.006 (2)0.017 (3)0.016 (2)0.0058 (19)0.0029 (18)0.006 (2)
O180.0116 (17)0.026 (2)0.0170 (17)0.0135 (16)0.0056 (14)0.0040 (15)
O170.0187 (18)0.025 (2)0.0133 (17)0.0179 (16)0.0065 (14)0.0014 (15)
O110.0230 (19)0.021 (2)0.0082 (16)0.0068 (16)0.0034 (14)−0.0011 (15)
O120.028 (2)0.028 (2)0.041 (2)0.0201 (19)0.0204 (19)0.0099 (19)
C110.013 (2)0.012 (2)0.019 (2)0.009 (2)0.0114 (19)0.005 (2)
C120.018 (3)0.011 (2)0.018 (2)0.006 (2)0.007 (2)0.002 (2)
O20.026 (2)0.044 (3)0.0178 (18)0.027 (2)0.0004 (16)0.0021 (18)
C20.026 (3)0.019 (3)0.010 (2)0.012 (2)0.010 (2)0.002 (2)
C30.022 (3)0.020 (3)0.018 (3)0.012 (2)0.007 (2)−0.002 (2)
O30.040 (2)0.020 (2)0.033 (2)0.0141 (19)0.0231 (19)0.0118 (18)
C130.018 (2)0.016 (3)0.012 (2)0.010 (2)0.0043 (19)0.000 (2)
O130.029 (2)0.0149 (19)0.0237 (19)0.0093 (16)0.0168 (16)0.0079 (15)
O140.0086 (16)0.0141 (18)0.0141 (17)0.0046 (14)0.0031 (13)0.0054 (14)
O40.025 (2)0.0138 (19)0.0214 (19)0.0088 (16)0.0164 (16)0.0019 (15)
Re20.00971 (10)0.01041 (10)0.00854 (9)0.00554 (8)0.00342 (7)0.00128 (7)
Re10.01226 (10)0.01220 (11)0.00847 (9)0.00860 (8)0.00437 (7)0.00248 (8)
C10.016 (2)0.017 (3)0.023 (3)0.011 (2)0.009 (2)0.012 (2)
O10.039 (2)0.028 (2)0.0169 (19)0.0175 (19)0.0158 (17)0.0020 (17)

Geometric parameters (Å, °)

N1—C91.343 (5)C7—C101.493 (6)
N1—C51.357 (5)C20—O181.215 (5)
N1—Re12.180 (4)C20—O171.309 (5)
O5—C41.261 (5)C19—N21.337 (5)
O5—Re12.153 (3)C19—H190.93
O6—C41.258 (5)N2—Re22.166 (4)
C4—O61.258 (5)O8—C101.223 (5)
C4—C51.508 (6)O7—C101.313 (5)
O15—C141.287 (5)O11—C111.161 (5)
O15—Re22.148 (3)O12—C121.135 (6)
C5—C61.372 (6)C11—Re21.892 (5)
O16—C141.227 (5)C12—Re21.947 (5)
C15—N21.351 (5)O2—C21.164 (6)
C15—C161.368 (6)C2—Re11.906 (5)
C15—C141.508 (6)C3—O31.165 (6)
C18—C191.376 (6)C3—Re11.885 (6)
C18—C171.385 (6)C13—O131.169 (6)
C18—H180.93C13—Re21.883 (5)
C17—C161.395 (6)O14—Re22.153 (3)
C17—C201.496 (6)O14—H14B0.85 (4)
C16—H160.93O14—H14A0.85 (4)
C8—C91.379 (6)O4—Re12.170 (3)
C8—C71.390 (6)O4—H4A0.85 (5)
C8—H80.93O4—H4B0.85 (5)
C6—C71.388 (6)Re1—C11.915 (5)
C6—H60.93C1—O11.151 (5)
C9—H90.93
C9—N1—C5117.6 (4)C15—N2—Re2115.9 (3)
C9—N1—Re1126.4 (3)C10—O7—H7109.5
C5—N1—Re1115.9 (3)O8—C10—O7125.2 (4)
C4—O5—Re1118.5 (3)O8—C10—C7121.8 (4)
O6—C4—O5122.9 (4)O7—C10—C7113.0 (4)
O6—C4—O5122.9 (4)C20—O17—H17109.5
O6—C4—C5119.9 (4)O11—C11—Re2175.5 (4)
O6—C4—C5119.9 (4)O12—C12—Re2179.4 (5)
O5—C4—C5117.2 (4)O2—C2—Re1179.9 (5)
C14—O15—Re2118.6 (3)O3—C3—Re1176.0 (5)
N1—C5—C6123.1 (4)O13—C13—Re2178.8 (4)
N1—C5—C4113.5 (4)Re2—O14—H14B116 (3)
C6—C5—C4123.3 (4)Re2—O14—H14A121 (3)
N2—C15—C16122.9 (4)H14B—O14—H14A112 (3)
N2—C15—C14114.7 (4)Re1—O4—H4A124 (3)
C16—C15—C14122.3 (4)Re1—O4—H4B121 (3)
O16—C14—O15124.0 (4)H4A—O4—H4B110 (3)
O16—C14—C15120.6 (4)C13—Re2—C1188.2 (2)
O15—C14—C15115.4 (4)C13—Re2—C1287.6 (2)
C19—C18—C17119.4 (4)C11—Re2—C1289.52 (19)
C19—C18—H18120.3C13—Re2—O1597.19 (16)
C17—C18—H18120.3C11—Re2—O15170.52 (16)
C18—C17—C16118.9 (4)C12—Re2—O1598.45 (16)
C18—C17—C20118.5 (4)C13—Re2—O14174.48 (16)
C16—C17—C20122.6 (4)C11—Re2—O1495.63 (16)
C15—C16—C17118.2 (4)C12—Re2—O1496.35 (17)
C15—C16—H16120.9O15—Re2—O1478.48 (12)
C17—C16—H16120.9C13—Re2—N296.92 (17)
C9—C8—C7119.0 (4)C11—Re2—N296.70 (16)
C9—C8—H8120.5C12—Re2—N2172.39 (16)
C7—C8—H8120.5O15—Re2—N274.98 (12)
C5—C6—C7118.6 (4)O14—Re2—N278.73 (13)
C5—C6—H6120.7C3—Re1—C288.6 (2)
C7—C6—H6120.7C3—Re1—C188.1 (2)
N1—C9—C8122.7 (4)C2—Re1—C188.6 (2)
N1—C9—H9118.7C3—Re1—O595.56 (17)
C8—C9—H9118.7C2—Re1—O598.77 (15)
C6—C7—C8119.0 (4)C1—Re1—O5171.85 (16)
C6—C7—C10119.0 (4)C3—Re1—O4176.21 (16)
C8—C7—C10122.0 (4)C2—Re1—O492.71 (18)
O18—C20—O17124.8 (4)C1—Re1—O495.49 (17)
O18—C20—C17120.7 (4)O5—Re1—O480.73 (12)
O17—C20—C17114.5 (4)C3—Re1—N196.75 (18)
N2—C19—C18121.8 (4)C2—Re1—N1171.93 (16)
N2—C19—H19119.1C1—Re1—N197.60 (17)
C18—C19—H19119.1O5—Re1—N174.77 (12)
C19—N2—C15118.7 (4)O4—Re1—N181.58 (14)
C19—N2—Re2125.3 (3)O1—C1—Re1176.6 (4)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O7—H7···O15i0.821.812.595 (4)160.
O4—H4B···O16ii0.85 (5)2.51 (5)2.920 (5)111 (4)
O4—H4B···O8iii0.85 (5)2.01 (3)2.780 (5)150 (5)
O4—H4B···O16ii0.85 (5)2.51 (5)2.920 (5)111 (4)
O14—H14B···O60.85 (5)1.84 (2)2.671 (5)169 (5)
O14—H14A···O18iii0.84 (2)1.87 (2)2.674 (4)161 (5)
O17—H17···O6iv0.821.782.602 (4)177.
C8—H8···O13v0.932.583.253 (5)130.
C6—H6···O17iv0.932.553.426 (5)156.
C19—H19···O2vi0.932.53.131 (5)126.

Symmetry codes: (i) x+1, y, z+1; (ii) x, y, z+1; (iii) x−1, y, z; (iv) −x+1, −y, −z; (v) −x+1, −y+1, −z+1; (vi) x+1, y, z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: NG2479).

References

  • Alberto, R., Schibli, R. & Schubiger, P. A. (1996). Polyhedron, 15, 1079–1083.
  • Alvarez, C. M., Garcia-Rodriguez, R. & Miguel, D. (2007). Dalton Trans. pp. 3546–3554. [PubMed]
  • Brandenberg, K. & Putz, H. (2005). DIAMOND Crystal Impact GbR, Bonn, Germany.
  • Bruker (2004). SAINT-Plus (including 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. [PubMed]
  • Roodt, A., Otto, S. & Steyl, G. (2003). Coord. Chem. Rev.245, 121–129.
  • Schutte, M., Visser, H. G. & Steyl, G. (2007). Acta Cryst. E63, m3195–m3196.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Wang, W., Spingler, B. & Alberto, R. (2003). Inorg. Chim. Acta, 355, 386–391.

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