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Acta Cryst. (2008). E64, m1226-m1227    [ doi:10.1107/S160053680802761X ]

Aquatricarbonyl(4-carboxypyridine-2-carboxylato-[kappa]2N,O2)rhenium(I)

M. Schutte and H. G. Visser

Abstract top

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.

Comment top

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.

Related literature top

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

Experimental top

[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 top

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).

Computing details top

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

Figures top
[Figure 1] Fig. 1. Representation of the title compound, showing the numbering scheme and displacement ellipsoids (50% probability).
Aquatricarbonyl(4-carboxypyridine-2-carboxylato- κ2N,O2)rhenium(I) top
Crystal data top
[Re(C7H4NO4)(CO)3(H2O)]Z = 4
Mr = 454.37F(000) = 848.0
Triclinic, P1Dx = 2.473 Mg m−3
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 mm−1
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 top
Bruker APEX
diffractometer		4869 reflections with I > 2σ(I)
φ 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 top
Refinement on F27 restraints
Least-squares matrix: fullH atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.027 w = 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 Å−3
5848 reflectionsΔρmin = −1.80 e Å−3
373 parameters
Crystal data top
[Re(C7H4NO4)(CO)3(H2O)]γ = 111.346 (4)°
Mr = 454.37V = 1220.4 (3) Å3
Triclinic, P1Z = 4
a = 9.5024 (11) ÅMo Kα radiation
b = 12.4254 (16) ŵ = 10.00 mm−1
c = 12.4889 (16) ÅT = 100 K
α = 101.799 (4)°0.27 × 0.17 × 0.05 mm
β = 107.943 (4)°
Data collection top
Bruker APEX
diffractometer		4869 reflections with I > 2σ(I)
Absorption correction: multi-scan
(SADABS; Bruker, 2004)		Rint = 0.037
Tmin = 0.140, Tmax = 0.605θmax = 28.3°
15096 measured reflectionsStandard reflections: 0
5048 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.027H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.065Δρmax = 1.21 e Å−3
S = 1.05Δρmin = −1.80 e Å−3
5848 reflectionsAbsolute structure: ?
373 parametersFlack parameter: ?
7 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
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) top
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, °) top
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, °) top
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.
Table 1
Selected geometric parameters (Å, °) top
N1—Re12.180 (4)C2—Re11.906 (5)
O5—Re12.153 (3)C3—Re11.885 (6)
O15—Re22.148 (3)C13—Re21.883 (5)
N2—Re22.166 (4)O14—Re22.153 (3)
C11—Re21.892 (5)O4—Re12.170 (3)
C12—Re21.947 (5)Re1—C11.915 (5)
C11—Re2—C1289.52 (19)O15—Re2—N274.98 (12)
C11—Re2—O15170.52 (16)C2—Re1—O598.77 (15)
C12—Re2—O1598.45 (16)C1—Re1—O495.49 (17)
C11—Re2—O1495.63 (16)O5—Re1—O480.73 (12)
C12—Re2—O1496.35 (17)O5—Re1—N174.77 (12)
O15—Re2—O1478.48 (12)
Table 2
Hydrogen-bond geometry (Å, °) top
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)
Symmetry codes: (i) x+1, y, z+1; (ii) x, y, z+1; (iii) x−1, y, z.
Acknowledgements top

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

references
References top

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