Aqua­tricarbon­yl(4-carboxy­pyridine-2-carboxyl­ato-κ2N,O2)rhenium(I)

Schutte, M.; Visser, H.G.

doi:10.1107/S160053680802761X

metal-organic compounds

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ISSN: 2056-9890

Volume 64| Part 10| October 2008| Pages m1226-m1227

doi:10.1107/S160053680802761X

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Aquatricarbonyl(4-carboxypyridine-2-carboxylato-κ²N,O²)rhenium(I)

Marietjie Schutte ^a and Hendrik G. Visser ^a ^*

^aDepartment of Chemistry, University of the Free State, PO Box 339, Bloemfontein 9300, South Africa
^*Correspondence e-mail: visserhg.sci@ufs.ac.za

(Received 25 July 2008; accepted 28 August 2008; online 6 September 2008)

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 ). 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

Crystal data

[Re(C₇H₄NO₄)(CO)₃(H₂O)]
M_r = 454.37
Triclinic, $[P \overline 1]$
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 ) 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[F² > 2σ(F²)] = 0.026
wR(F²) = 0.065
S = 1.05
5848 reflections
373 parameters
7 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 1.21 e Å⁻³
Δρ_min = −1.80 e Å⁻³

Table 1
Selected geometric parameters (Å, °)

N1—Re1	2.180 (4)
O5—Re1	2.153 (3)
O15—Re2	2.148 (3)
N2—Re2	2.166 (4)
C11—Re2	1.892 (5)
C12—Re2	1.947 (5)
C2—Re1	1.906 (5)
C3—Re1	1.885 (6)
C13—Re2	1.883 (5)
O14—Re2	2.153 (3)
O4—Re1	2.170 (3)
Re1—C1	1.915 (5)

C11—Re2—C12	89.52 (19)
C11—Re2—O15	170.52 (16)
C12—Re2—O15	98.45 (16)
C11—Re2—O14	95.63 (16)
C12—Re2—O14	96.35 (17)
O15—Re2—O14	78.48 (12)
O15—Re2—N2	74.98 (12)
C2—Re1—O5	98.77 (15)
C1—Re1—O4	95.49 (17)
O5—Re1—O4	80.73 (12)
O5—Re1—N1	74.77 (12)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O7—H7⋯O15ⁱ	0.82	1.81	2.595 (4)	160
O4—H4B⋯O16ⁱⁱ	0.85 (5)	2.51 (5)	2.920 (5)	111 (4)
O4—H4B⋯O8ⁱⁱⁱ	0.85 (5)	2.01 (3)	2.780 (5)	150 (5)
O4—H4B⋯O16ⁱⁱ	0.85 (5)	2.51 (5)	2.920 (5)	111 (4)
O14—H14B⋯O6	0.85 (5)	1.84 (2)	2.671 (5)	169 (5)
O14—H14A⋯O18ⁱⁱⁱ	0.840 (18)	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.

Data collection: APEX2 (Bruker, 2005 ); cell refinement: SAINT-Plus (Bruker, 2004); data reduction: SAINT-Plus; 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.

Supporting information

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

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

checkCIF report

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%).

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

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
M_r = 454.37	F(000) = 848.0
Triclinic, P1	D_x = 2.473 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.5024 (11) Å	Cell parameters from 7140 reflections
b = 12.4254 (16) Å	θ = 2.8–28.3°
c = 12.4889 (16) Å	µ = 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 scans	R_int = 0.037
Absorption correction: multi-scan (SADABS; Bruker, 2004)	θ_max = 28.3°, θ_min = 1.8°
T_min = 0.140, T_max = 0.605	h = −12→12
15096 measured reflections	k = −16→15
5048 independent reflections	l = −16→16

Refinement top

Refinement on F²	7 restraints
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F² > 2σ(F²)] = 0.027	w = 1/[σ²(F_o²) + (0.0251P)²] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.065	(Δ/σ)_max = 0.015
S = 1.05	Δρ_max = 1.21 e Å⁻³
5848 reflections	Δρ_min = −1.80 e Å⁻³
373 parameters

Crystal data top

[Re(C₇H₄NO₄)(CO)₃(H₂O)]	γ = 111.346 (4)°
M_r = 454.37	V = 1220.4 (3) Å³
Triclinic, P1	Z = 4
a = 9.5024 (11) Å	Mo Kα radiation
b = 12.4254 (16) Å	µ = 10.00 mm⁻¹
c = 12.4889 (16) Å	T = 100 K
α = 101.799 (4)°	0.27 × 0.17 × 0.05 mm
β = 107.943 (4)°

Data collection top

Bruker APEX diffractometer	5048 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2004)	4869 reflections with I > 2σ(I)
T_min = 0.140, T_max = 0.605	R_int = 0.037
15096 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.027	7 restraints
wR(F²) = 0.065	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	Δρ_max = 1.21 e Å⁻³
5848 reflections	Δρ_min = −1.80 e Å⁻³
373 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

	x	y	z	U_iso*/U_eq
N1	0.3078 (4)	0.2654 (3)	0.5400 (3)	0.0095 (8)
O5	0.1030 (4)	0.1933 (3)	0.3130 (2)	0.0113 (7)
O6	0.2391 (4)	0.1072 (3)	0.2433 (3)	0.0152 (7)
C4	0.2193 (6)	0.1635 (4)	0.3289 (4)	0.0116 (9)
O15	0.0841 (4)	0.2152 (3)	−0.1450 (3)	0.0112 (7)
C5	0.3392 (6)	0.1998 (4)	0.4572 (4)	0.0102 (9)
O16	0.0735 (4)	0.0827 (3)	−0.3002 (3)	0.0160 (7)
C15	0.3019 (5)	0.1585 (4)	−0.1099 (4)	0.0097 (9)
C14	0.1407 (6)	0.1487 (4)	−0.1934 (4)	0.0118 (10)
C18	0.5968 (5)	0.1949 (4)	0.0518 (4)	0.0116 (9)
H18	0.6981	0.2089	0.1084	0.014*
C17	0.5336 (6)	0.1168 (4)	−0.0662 (4)	0.0115 (9)
C16	0.3816 (5)	0.0981 (4)	−0.1491 (4)	0.0106 (9)
H16	0.3358	0.0459	−0.2288	0.013*
C8	0.5409 (6)	0.2756 (4)	0.6944 (4)	0.0127 (10)
H8	0.6081	0.3019	0.7761	0.015*
C6	0.4696 (6)	0.1716 (4)	0.4875 (4)	0.0129 (10)
H6	0.4884	0.1278	0.4282	0.015*
C9	0.4082 (5)	0.3013 (4)	0.6568 (4)	0.0122 (10)
H9	0.3874	0.3453	0.7146	0.015*
C7	0.5727 (5)	0.2098 (4)	0.6085 (4)	0.0105 (9)
C20	0.6310 (6)	0.0551 (4)	−0.0994 (4)	0.0131 (10)
C19	0.5084 (5)	0.2516 (4)	0.0845 (4)	0.0118 (10)
H19	0.5507	0.3031	0.1641	0.014*
N2	0.3633 (4)	0.2346 (3)	0.0051 (3)	0.0092 (8)
O8	0.7441 (4)	0.1233 (3)	0.5666 (3)	0.0200 (8)
O7	0.8100 (4)	0.2290 (3)	0.7589 (3)	0.0190 (8)
H7	0.8878	0.2118	0.773	0.029*
C10	0.7178 (5)	0.1827 (4)	0.6423 (4)	0.0134 (10)
O18	0.7570 (4)	0.0669 (3)	−0.0231 (3)	0.0174 (8)
O17	0.5674 (4)	−0.0113 (3)	−0.2139 (3)	0.0176 (8)
H17	0.6264	−0.0424	−0.2258	0.026*
O11	0.4169 (4)	0.4220 (3)	0.3181 (3)	0.0206 (8)
O12	−0.0486 (5)	0.3985 (3)	0.0753 (3)	0.0290 (9)
C11	0.3339 (6)	0.3833 (4)	0.2154 (4)	0.0129 (10)
C12	0.0473 (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)
C3	0.2069 (6)	0.4532 (5)	0.4629 (4)	0.0211 (12)
O3	0.2698 (5)	0.5484 (3)	0.4535 (3)	0.0283 (9)
C13	0.3283 (6)	0.4712 (5)	0.0407 (4)	0.0162 (10)
O13	0.4026 (4)	0.5690 (3)	0.0395 (3)	0.0209 (8)
O14	0.0791 (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*
H14B	0.123 (5)	0.112 (5)	0.098 (3)	0.029*
H14A	−0.025 (2)	0.093 (4)	0.010 (4)	0.029*
Re2	0.20999 (2)	0.315032 (16)	0.046124 (15)	0.00973 (6)
Re1	0.09158 (2)	0.296297 (16)	0.468442 (15)	0.01020 (6)
C1	0.1002 (6)	0.3789 (5)	0.6194 (4)	0.0165 (10)
O1	0.1138 (5)	0.4303 (3)	0.7126 (3)	0.0272 (9)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0096 (18)	0.013 (2)	0.0088 (18)	0.0082 (16)	0.0031 (15)	0.0057 (16)
O5	0.0128 (16)	0.0157 (18)	0.0070 (15)	0.0087 (14)	0.0052 (13)	0.0014 (13)
O6	0.0183 (17)	0.0185 (19)	0.0109 (16)	0.0125 (15)	0.0057 (14)	0.0022 (14)
C4	0.016 (2)	0.013 (2)	0.013 (2)	0.010 (2)	0.0097 (19)	0.0047 (19)
O15	0.0142 (16)	0.0144 (17)	0.0063 (14)	0.0101 (14)	0.0035 (13)	0.0007 (13)
C5	0.012 (2)	0.008 (2)	0.006 (2)	0.0038 (18)	0.0014 (17)	−0.0007 (17)
O16	0.0185 (18)	0.0204 (19)	0.0076 (15)	0.0131 (15)	0.0024 (13)	−0.0010 (14)
C15	0.012 (2)	0.008 (2)	0.009 (2)	0.0047 (18)	0.0040 (18)	0.0034 (18)
C14	0.012 (2)	0.016 (3)	0.010 (2)	0.008 (2)	0.0044 (18)	0.0060 (19)
C18	0.006 (2)	0.017 (3)	0.009 (2)	0.0058 (19)	0.0008 (17)	0.0032 (19)
C17	0.015 (2)	0.011 (2)	0.014 (2)	0.0092 (19)	0.0085 (19)	0.0059 (19)
C16	0.011 (2)	0.010 (2)	0.008 (2)	0.0039 (19)	0.0039 (17)	0.0016 (18)
C8	0.012 (2)	0.016 (2)	0.006 (2)	0.006 (2)	0.0017 (17)	0.0023 (18)
C6	0.013 (2)	0.010 (2)	0.013 (2)	0.0028 (19)	0.0073 (19)	0.0026 (19)
C9	0.013 (2)	0.015 (2)	0.006 (2)	0.008 (2)	0.0025 (18)	−0.0010 (18)
C7	0.005 (2)	0.014 (2)	0.011 (2)	0.0053 (18)	0.0015 (17)	0.0029 (19)
C20	0.012 (2)	0.014 (2)	0.016 (2)	0.008 (2)	0.0073 (19)	0.005 (2)
C19	0.010 (2)	0.014 (2)	0.008 (2)	0.0056 (19)	0.0030 (18)	0.0001 (18)
N2	0.0081 (18)	0.010 (2)	0.0085 (18)	0.0053 (16)	0.0021 (14)	0.0014 (15)
O8	0.0175 (18)	0.027 (2)	0.0152 (17)	0.0143 (16)	0.0046 (14)	0.0022 (15)
O7	0.0150 (17)	0.029 (2)	0.0117 (16)	0.0145 (16)	0.0008 (14)	0.0025 (15)
C10	0.006 (2)	0.017 (3)	0.016 (2)	0.0058 (19)	0.0029 (18)	0.006 (2)
O18	0.0116 (17)	0.026 (2)	0.0170 (17)	0.0135 (16)	0.0056 (14)	0.0040 (15)
O17	0.0187 (18)	0.025 (2)	0.0133 (17)	0.0179 (16)	0.0065 (14)	0.0014 (15)
O11	0.0230 (19)	0.021 (2)	0.0082 (16)	0.0068 (16)	0.0034 (14)	−0.0011 (15)
O12	0.028 (2)	0.028 (2)	0.041 (2)	0.0201 (19)	0.0204 (19)	0.0099 (19)
C11	0.013 (2)	0.012 (2)	0.019 (2)	0.009 (2)	0.0114 (19)	0.005 (2)
C12	0.018 (3)	0.011 (2)	0.018 (2)	0.006 (2)	0.007 (2)	0.002 (2)
O2	0.026 (2)	0.044 (3)	0.0178 (18)	0.027 (2)	0.0004 (16)	0.0021 (18)
C2	0.026 (3)	0.019 (3)	0.010 (2)	0.012 (2)	0.010 (2)	0.002 (2)
C3	0.022 (3)	0.020 (3)	0.018 (3)	0.012 (2)	0.007 (2)	−0.002 (2)
O3	0.040 (2)	0.020 (2)	0.033 (2)	0.0141 (19)	0.0231 (19)	0.0118 (18)
C13	0.018 (2)	0.016 (3)	0.012 (2)	0.010 (2)	0.0043 (19)	0.000 (2)
O13	0.029 (2)	0.0149 (19)	0.0237 (19)	0.0093 (16)	0.0168 (16)	0.0079 (15)
O14	0.0086 (16)	0.0141 (18)	0.0141 (17)	0.0046 (14)	0.0031 (13)	0.0054 (14)
O4	0.025 (2)	0.0138 (19)	0.0214 (19)	0.0088 (16)	0.0164 (16)	0.0019 (15)
Re2	0.00971 (10)	0.01041 (10)	0.00854 (9)	0.00554 (8)	0.00342 (7)	0.00128 (7)
Re1	0.01226 (10)	0.01220 (11)	0.00847 (9)	0.00860 (8)	0.00437 (7)	0.00248 (8)
C1	0.016 (2)	0.017 (3)	0.023 (3)	0.011 (2)	0.009 (2)	0.012 (2)
O1	0.039 (2)	0.028 (2)	0.0169 (19)	0.0175 (19)	0.0158 (17)	0.0020 (17)

Geometric parameters (Å, º) top

N1—C9	1.343 (5)	C7—C10	1.493 (6)
N1—C5	1.357 (5)	C20—O18	1.215 (5)
N1—Re1	2.180 (4)	C20—O17	1.309 (5)
O5—C4	1.261 (5)	C19—N2	1.337 (5)
O5—Re1	2.153 (3)	C19—H19	0.93
O6—C4	1.258 (5)	N2—Re2	2.166 (4)
C4—O6	1.258 (5)	O8—C10	1.223 (5)
C4—C5	1.508 (6)	O7—C10	1.313 (5)
O15—C14	1.287 (5)	O11—C11	1.161 (5)
O15—Re2	2.148 (3)	O12—C12	1.135 (6)
C5—C6	1.372 (6)	C11—Re2	1.892 (5)
O16—C14	1.227 (5)	C12—Re2	1.947 (5)
C15—N2	1.351 (5)	O2—C2	1.164 (6)
C15—C16	1.368 (6)	C2—Re1	1.906 (5)
C15—C14	1.508 (6)	C3—O3	1.165 (6)
C18—C19	1.376 (6)	C3—Re1	1.885 (6)
C18—C17	1.385 (6)	C13—O13	1.169 (6)
C18—H18	0.93	C13—Re2	1.883 (5)
C17—C16	1.395 (6)	O14—Re2	2.153 (3)
C17—C20	1.496 (6)	O14—H14B	0.85 (4)
C16—H16	0.93	O14—H14A	0.85 (4)
C8—C9	1.379 (6)	O4—Re1	2.170 (3)
C8—C7	1.390 (6)	O4—H4A	0.85 (5)
C8—H8	0.93	O4—H4B	0.85 (5)
C6—C7	1.388 (6)	Re1—C1	1.915 (5)
C6—H6	0.93	C1—O1	1.151 (5)
C9—H9	0.93

C9—N1—C5	117.6 (4)	C15—N2—Re2	115.9 (3)
C9—N1—Re1	126.4 (3)	C10—O7—H7	109.5
C5—N1—Re1	115.9 (3)	O8—C10—O7	125.2 (4)
C4—O5—Re1	118.5 (3)	O8—C10—C7	121.8 (4)
O6—C4—O5	122.9 (4)	O7—C10—C7	113.0 (4)
O6—C4—O5	122.9 (4)	C20—O17—H17	109.5
O6—C4—C5	119.9 (4)	O11—C11—Re2	175.5 (4)
O6—C4—C5	119.9 (4)	O12—C12—Re2	179.4 (5)
O5—C4—C5	117.2 (4)	O2—C2—Re1	179.9 (5)
C14—O15—Re2	118.6 (3)	O3—C3—Re1	176.0 (5)
N1—C5—C6	123.1 (4)	O13—C13—Re2	178.8 (4)
N1—C5—C4	113.5 (4)	Re2—O14—H14B	116 (3)
C6—C5—C4	123.3 (4)	Re2—O14—H14A	121 (3)
N2—C15—C16	122.9 (4)	H14B—O14—H14A	112 (3)
N2—C15—C14	114.7 (4)	Re1—O4—H4A	124 (3)
C16—C15—C14	122.3 (4)	Re1—O4—H4B	121 (3)
O16—C14—O15	124.0 (4)	H4A—O4—H4B	110 (3)
O16—C14—C15	120.6 (4)	C13—Re2—C11	88.2 (2)
O15—C14—C15	115.4 (4)	C13—Re2—C12	87.6 (2)
C19—C18—C17	119.4 (4)	C11—Re2—C12	89.52 (19)
C19—C18—H18	120.3	C13—Re2—O15	97.19 (16)
C17—C18—H18	120.3	C11—Re2—O15	170.52 (16)
C18—C17—C16	118.9 (4)	C12—Re2—O15	98.45 (16)
C18—C17—C20	118.5 (4)	C13—Re2—O14	174.48 (16)
C16—C17—C20	122.6 (4)	C11—Re2—O14	95.63 (16)
C15—C16—C17	118.2 (4)	C12—Re2—O14	96.35 (17)
C15—C16—H16	120.9	O15—Re2—O14	78.48 (12)
C17—C16—H16	120.9	C13—Re2—N2	96.92 (17)
C9—C8—C7	119.0 (4)	C11—Re2—N2	96.70 (16)
C9—C8—H8	120.5	C12—Re2—N2	172.39 (16)
C7—C8—H8	120.5	O15—Re2—N2	74.98 (12)
C5—C6—C7	118.6 (4)	O14—Re2—N2	78.73 (13)
C5—C6—H6	120.7	C3—Re1—C2	88.6 (2)
C7—C6—H6	120.7	C3—Re1—C1	88.1 (2)
N1—C9—C8	122.7 (4)	C2—Re1—C1	88.6 (2)
N1—C9—H9	118.7	C3—Re1—O5	95.56 (17)
C8—C9—H9	118.7	C2—Re1—O5	98.77 (15)
C6—C7—C8	119.0 (4)	C1—Re1—O5	171.85 (16)
C6—C7—C10	119.0 (4)	C3—Re1—O4	176.21 (16)
C8—C7—C10	122.0 (4)	C2—Re1—O4	92.71 (18)
O18—C20—O17	124.8 (4)	C1—Re1—O4	95.49 (17)
O18—C20—C17	120.7 (4)	O5—Re1—O4	80.73 (12)
O17—C20—C17	114.5 (4)	C3—Re1—N1	96.75 (18)
N2—C19—C18	121.8 (4)	C2—Re1—N1	171.93 (16)
N2—C19—H19	119.1	C1—Re1—N1	97.60 (17)
C18—C19—H19	119.1	O5—Re1—N1	74.77 (12)
C19—N2—C15	118.7 (4)	O4—Re1—N1	81.58 (14)
C19—N2—Re2	125.3 (3)	O1—C1—Re1	176.6 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O7—H7···O15ⁱ	0.82	1.81	2.595 (4)	160
O4—H4B···O16ⁱⁱ	0.85 (5)	2.51 (5)	2.920 (5)	111 (4)
O4—H4B···O8ⁱⁱⁱ	0.85 (5)	2.01 (3)	2.780 (5)	150 (5)
O4—H4B···O16ⁱⁱ	0.85 (5)	2.51 (5)	2.920 (5)	111 (4)
O14—H14B···O6	0.85 (5)	1.84 (2)	2.671 (5)	169 (5)
O14—H14A···O18ⁱⁱⁱ	0.84 (2)	1.87 (2)	2.674 (4)	161 (5)
O17—H17···O6^iv	0.82	1.78	2.602 (4)	177
C8—H8···O13^v	0.93	2.58	3.253 (5)	130
C6—H6···O17^iv	0.93	2.55	3.426 (5)	156
C19—H19···O2^vi	0.93	2.5	3.131 (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.

Experimental details

Crystal data
Chemical formula	[Re(C₇H₄NO₄)(CO)₃(H₂O)]
M_r	454.37
Crystal system, space group	Triclinic, P1
Temperature (K)	100
a, b, c (Å)	9.5024 (11), 12.4254 (16), 12.4889 (16)
α, β, γ (°)	101.799 (4), 107.943 (4), 111.346 (4)
V (Å³)	1220.4 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	10.00
Crystal size (mm)	0.27 × 0.17 × 0.05

Data collection
Diffractometer	Bruker APEX diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2004)
T_min, T_max	0.140, 0.605
No. of measured, independent and observed [I > 2σ(I)] reflections	15096, 5048, 4869
R_int	0.037
(sin θ/λ)_max (Å⁻¹)	0.668

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.027, 0.065, 1.05
No. of reflections	5848
No. of parameters	373
No. of restraints	7
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	1.21, −1.80

Computer programs: APEX2 (Bruker, 2005), SAINT-Plus (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), DIAMOND (Brandenberg & Putz, 2005) and ORTEP-3 (Farrugia, 1999).

Selected geometric parameters (Å, º) top

N1—Re1	2.180 (4)	C2—Re1	1.906 (5)
O5—Re1	2.153 (3)	C3—Re1	1.885 (6)
O15—Re2	2.148 (3)	C13—Re2	1.883 (5)
N2—Re2	2.166 (4)	O14—Re2	2.153 (3)
C11—Re2	1.892 (5)	O4—Re1	2.170 (3)
C12—Re2	1.947 (5)	Re1—C1	1.915 (5)

C11—Re2—C12	89.52 (19)	O15—Re2—N2	74.98 (12)
C11—Re2—O15	170.52 (16)	C2—Re1—O5	98.77 (15)
C12—Re2—O15	98.45 (16)	C1—Re1—O4	95.49 (17)
C11—Re2—O14	95.63 (16)	O5—Re1—O4	80.73 (12)
C12—Re2—O14	96.35 (17)	O5—Re1—N1	74.77 (12)
O15—Re2—O14	78.48 (12)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O7—H7···O15ⁱ	0.82	1.81	2.595 (4)	159.7
O4—H4B···O16ⁱⁱ	0.85 (5)	2.51 (5)	2.920 (5)	111 (4)
O4—H4B···O8ⁱⁱⁱ	0.85 (5)	2.01 (3)	2.780 (5)	150 (5)
O4—H4B···O16ⁱⁱ	0.85 (5)	2.51 (5)	2.920 (5)	111 (4)
O14—H14B···O6	0.85 (5)	1.84 (2)	2.671 (5)	169 (5)
O14—H14A···O18ⁱⁱⁱ	0.840 (18)	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

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.

References

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