(μ1-Methano­lato-κ1O)-μ1-methoxo-κ1O-(μ2-2-amino-1-methyl-5H-imidazol-4-one-κ2N:N′)-hexa­carbonyl­dirhenium(I)

Schutte, M.; Visser, H.G.; Roodt, A.

doi:10.1107/S1600536812041700

metal-organic compounds

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ISSN: 2056-9890

Volume 68| Part 11| November 2012| Pages m1359-m1360

doi:10.1107/S1600536812041700

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(μ₁-Methanolato-κ¹O)-μ₁-methoxo-κ¹O-(μ₂-2-amino-1-methyl-5H-imidazol-4-one-κ²N:N′)-hexacarbonyldirhenium(I)

M. Schutte,^a ^* H. G. Visser ^a and A. Roodt ^a

^aDepartment of Chemistry, University of the Free State, PO Box 339, Bloemfontein, 9301, South Africa
^*Correspondence e-mail: schuttem@ufs.ac.za

(Received 27 September 2012; accepted 5 October 2012; online 13 October 2012)

In the title compound, [Re₂(CH₃O)₂(CO)₆(C₄H₆N₃O)], the two Re^I atoms are linked by a methoxo and methanolato bridge, as well as by a creatinine ligand that coordinates in a bidentate fashion. Three fac-carbonyl ligands occupy the rest of the slightly distorted octahedral geometry around each Re^I atom. The bridging methanolato and methoxo ligands are bent out of the Re₂O₂ plane by 49.2 (4) and 47.8 (3)° respectively. This is normally associated with a methanolato-bridging-type coordination rather that the more planar methoxo-type bridging. Furthermore, the creatinine bridging molecule is very slightly distorted from the Re₂N₂C plane, indicating that the pyrazolo N atom bonded to the Rh^I atom is not protonated. Charge balance can thus only be attained if one assumes a positional disorder for the methanolato/methoxo H atom. All attempts to locate disordered protons around these O atoms were unsuccessful. Four hydrogen bonds, one N—H⋯O and three C—H⋯O, are observed in the structure. The molecules pack in a head-to-head and tail-to-tail fashion when viewed along the c axis, in alternating columns.

Related literature

For the synthesis of the starting material, see: Alberto et al. (1996 ). For similar Re^I methoxy-bridged structures, see: Franklin et al. (2008 ); Klausmeyer & Beckles (2006 ). For structures of creatinine, see: Bell et al. (1995 ); du Pré & Mendel (1955 ). For structures with creatinine as a monodentate ligand, see: Canty et al. (1979 ); Mitewa et al. (2002 ); Matos Beja et al. (1991 ); Panfil et al. (1995 ). For a tetranuclear Re^I complex, see: Schutte et al. (2012a ). For similar Re^I structures, see: Schutte et al. (2011 , 2012b ,c ).

Experimental

Crystal data

[Re₂(CH₃O)₂(CO)₆(C₄H₆N₃O)]
M_r = 714.67
Orthorhombic, P b c n
a = 24.066 (2) Å
b = 10.0715 (8) Å
c = 14.5969 (11) Å
V = 3538.1 (5) Å³
Z = 8
Mo Kα radiation
μ = 13.73 mm⁻¹
T = 100 K
0.25 × 0.15 × 0.10 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2008 ) T_min = 0.174, T_max = 0.371
46753 measured reflections
4276 independent reflections
3920 reflections with I > 2σ(I)
R_int = 0.050

Refinement

R[F² > 2σ(F²)] = 0.030
wR(F²) = 0.078
S = 1.16
4269 reflections
236 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 2.32 e Å⁻³
Δρ_min = −2.30 e Å⁻³

Table 1
Selected bond lengths (Å)

Re1—C11	1.886 (6)
Re1—C13	1.908 (7)
Re1—C12	1.918 (8)
Re1—O2	2.149 (4)
Re1—N3	2.150 (5)
Re1—O1	2.153 (4)
Re2—C21	1.849 (5)
Re2—C22	1.935 (6)
Re2—C23	1.949 (6)
Re2—O2	2.065 (4)
Re2—O1	2.073 (4)
Re2—N1	2.136 (5)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3⋯O31ⁱ	0.92 (8)	2.17 (8)	3.061 (6)	162 (7)
C2—H2B⋯O13ⁱⁱ	0.96	2.54	3.453 (9)	159
C2—H2C⋯O23ⁱⁱ	0.96	2.61	3.504 (9)	154
C34—H34A⋯O31ⁱ	0.96	2.44	3.332 (7)	155
Symmetry codes: (i) $[x, -y+2, z+{\script{1\over 2}}]$ ; (ii) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, z]$ .

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT-Plus (Bruker, 2008); 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 (Brandenburg & Putz, 2005 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812041700/tk5155sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812041700/tk5155Isup2.hkl

checkCIF report

Comment top

C₁₂H₁₂N₃O₉Re₂ crystallized in the orthorhombic space group Pbcn with one unit in the asymmetric unit. The rhenium centres are linked with two methoxy bridges and a creatinine ligand (in a N,N'-bidentate fashion). Three facial tricarbonyl ligands occupy the other three positions on the distorted octahedron, Fig. 1 and Table 1. The Re—O—Re (104.01 (18)° and 104.4 (2)°) and O—Re—O (73.71 (16)° and 77.16 (17)°) bond angles compare well to the structure by Klausmeyer & Beckles (2006) that reported 103.66 (1)° and 103.33 (1)° (Re—O—Re) and 76.66 (1)° and 76.21 (1)° (O—Re—O), and to the structure by Franklin et al. (2008) that reported 108.24 (1)° and 108.24 (2)° (Re—O—Re) and 71.76 (12)° (O—Re—O) respectively. Creatinine is coordinated to various metal centres in a monodentate fashion (Canty et al. 1979, Mitewa et al. 2002, Matos Beja et al. 1991, Panfil et al. 1995) but no structure reports are found where creatinine is coordinated to a metal centre in a bidentate fashion. All bond distances and angles of creatinine in this structure compare well with that of the reported structures of the free ligand with the N—C—N angle the only exception with 121° (Bell et al., 1995) and 120° (du Pré & Mendel, 1955) reported for the free ligand and 123.7 (5)° for the coordinated ligand, respectively. The O—Re—O (73.71 (16)° and 77.16 (17)°) and Re—O—Re (104.01 (18)° and 104.4 (2)°) bond angles compare well to the tetranuclear rhenium(I) cubane-like molecule reported by Schutte et al. (2012a) with O—Re—O angles that vary between 73.5 (2)° and 75.0 (7)° and Re—O—Re angles that vary between 102.6 (3)° and 104.7 (2)°. This ligand, creatinine, forms part of an ongoing study where different N,N' bidentate and N,N',N'' tridentate ligands are synthesized and coordinated to the rhenium(I) metal centre (Schutte et al., 2011, 2012b, 2012c). Four intermolecular hydrogen bonds are observed in the structure, Table 2, i.e. one N—H···O and three C—H···O. When viewed along the c axis, the molecules pack in column-like structures in an alternating head-to-head and tail-to-tail fashion (Fig. 2).

Related literature top

For the synthesis of the starting material, see: Alberto et al. (1996). For similar Re^I methoxy-bridged structures, see: Franklin et al. (2008); Klausmeyer & Beckles (2006). For structures of creatinine, see: Bell et al. (1995); du Pré et al. (1955). For structures with creatinine as a monodentate ligand, see: Canty et al. (1979); Mitewa et al. (2002); Matos Beja et al. (1991); Panfil et al. (1995). For a tetranuclear Re^I complex, see: Schutte et al. (2012a). For similar Re^I structures, see: Schutte et al. (2011, 2012b,c).

Experimental top

[NEt₄]₂[Re(CO)₃Br₃] (500 mg, 0.650 mmol), as prepared by Alberto et al. (1996), was dissolved in 10 ml of water at pH 2. The pH was increased to pH 6 and after a slight colour change, creatinine (37 mg, 0.325 mmol) was added to the mixture and stirred for 6 h at room temperature. The yellow cuboidal crystals were obtained from the filtrate of the solution.

Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT-Plus (Bruker, 2008); data reduction: SAINT-Plus (Bruker, 2008); 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

	Fig. 1. Representation of the title compound, showing the numbering scheme and displacement ellipsoids (50% probability).
	Fig. 2. Packing and hydrogen interactions (dashed lines) of the title compound in the unit cell. Hydrogen atoms omitted for clarity.

(µ₁-Methanolato-κ¹O)-µ₁-methoxo-κ¹-O(µ₂-2-amino-1- methyl-5H-imidazol-4-one-κ²N:N')- hexacarbonyldirhenium(I) top

Crystal data top

[Re₂(CH₃O)₂(CO)₆(C₄H₆N₃O)]	F(000) = 2616
M_r = 714.67	D_x = 2.683 Mg m⁻³
Orthorhombic, Pbcn	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2n 2ab	Cell parameters from 9082 reflections
a = 24.066 (2) Å	θ = 3.0–28.3°
b = 10.0715 (8) Å	µ = 13.73 mm⁻¹
c = 14.5969 (11) Å	T = 100 K
V = 3538.1 (5) Å³	Cuboid, yellow
Z = 8	0.25 × 0.15 × 0.10 mm

Data collection top

Bruker APEXII CCD diffractometer	3920 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.050
ϕ and ω scans	θ_max = 28°, θ_min = 2.8°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −31→31
T_min = 0.174, T_max = 0.371	k = −13→12
46753 measured reflections	l = −19→18
4276 independent reflections

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.03	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.078	H atoms treated by a mixture of independent and constrained refinement
S = 1.16	w = 1/[σ²(F_o²) + (0.0246P)² + 32.0137P] where P = (F_o² + 2F_c²)/3
4269 reflections	(Δ/σ)_max = 0.006
236 parameters	Δρ_max = 2.32 e Å⁻³
0 restraints	Δρ_min = −2.30 e Å⁻³

Crystal data top

[Re₂(CH₃O)₂(CO)₆(C₄H₆N₃O)]	V = 3538.1 (5) Å³
M_r = 714.67	Z = 8
Orthorhombic, Pbcn	Mo Kα radiation
a = 24.066 (2) Å	µ = 13.73 mm⁻¹
b = 10.0715 (8) Å	T = 100 K
c = 14.5969 (11) Å	0.25 × 0.15 × 0.10 mm

Data collection top

Bruker APEXII CCD diffractometer	4276 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2008)	3920 reflections with I > 2σ(I)
T_min = 0.174, T_max = 0.371	R_int = 0.050
46753 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.03	0 restraints
wR(F²) = 0.078	H atoms treated by a mixture of independent and constrained refinement
S = 1.16	w = 1/[σ²(F_o²) + (0.0246P)² + 32.0137P] where P = (F_o² + 2F_c²)/3
4269 reflections	Δρ_max = 2.32 e Å⁻³
236 parameters	Δρ_min = −2.30 e Å⁻³

Special details top

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Re1	0.364485 (10)	0.71291 (2)	0.050452 (15)	0.01847 (7)
Re2	0.370469 (11)	0.72576 (2)	−0.177323 (15)	0.02132 (8)
O21	0.4552 (2)	0.6573 (5)	−0.3213 (3)	0.0324 (11)
O22	0.3040 (2)	0.8637 (5)	−0.3303 (3)	0.0358 (11)
O12	0.2927 (2)	0.8300 (5)	0.2038 (3)	0.0315 (10)
C21	0.4229 (2)	0.6840 (5)	−0.2654 (3)	0.0164 (10)
C12	0.3184 (4)	0.7864 (8)	0.1449 (5)	0.0397 (12)
C22	0.3280 (3)	0.8139 (6)	−0.2720 (4)	0.0225 (12)
O13	0.3108 (2)	0.4401 (5)	0.0824 (3)	0.0387 (12)
O23	0.3083 (2)	0.4642 (5)	−0.2175 (3)	0.0348 (11)
C13	0.3295 (3)	0.5449 (7)	0.0687 (4)	0.0265 (13)
C23	0.3310 (3)	0.5609 (6)	−0.2029 (4)	0.0229 (12)
O1	0.41283 (18)	0.6491 (4)	−0.0656 (2)	0.0201 (8)
O2	0.3181 (2)	0.7690 (5)	−0.0693 (3)	0.0262 (10)
C1	0.4321 (3)	0.5153 (6)	−0.0685 (4)	0.0280 (13)
H1C	0.401	0.4564	−0.0754	0.042*
H1A	0.4514	0.495	−0.0126	0.042*
H1B	0.457	0.5045	−0.1194	0.042*
C11	0.4133 (3)	0.6643 (5)	0.1458 (4)	0.0203 (11)
O11	0.4425 (2)	0.6333 (4)	0.2055 (3)	0.0294 (10)
O31	0.4263 (2)	0.9857 (4)	−0.2855 (3)	0.0277 (10)
N1	0.4107 (2)	0.9064 (5)	−0.1391 (3)	0.0230 (11)
N3	0.4054 (2)	0.8987 (5)	0.0237 (3)	0.0231 (11)
N2	0.4472 (3)	1.0758 (5)	−0.0571 (3)	0.0288 (13)
C33	0.4202 (3)	0.9583 (6)	−0.0515 (4)	0.0227 (12)
C31	0.4282 (3)	0.9978 (6)	−0.2020 (4)	0.0243 (12)
C34	0.4523 (3)	1.1691 (6)	0.0173 (4)	0.0285 (14)
H34C	0.4193	1.2223	0.0208	0.043*
H34B	0.4839	1.2254	0.007	0.043*
H34A	0.4571	1.1216	0.0738	0.043*
C32	0.4501 (3)	1.1178 (6)	−0.1519 (4)	0.0287 (14)
H32A	0.488	1.1377	−0.1699	0.034*
H32B	0.427	1.1951	−0.1628	0.034*
C2	0.2586 (4)	0.7391 (8)	−0.0714 (5)	0.0397 (12)
H2B	0.2411	0.7755	−0.0179	0.06*
H2A	0.2534	0.6446	−0.0724	0.06*
H2C	0.2423	0.7775	−0.1253	0.06*
H3	0.418 (3)	0.944 (8)	0.075 (5)	0.03 (2)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Re1	0.02881 (14)	0.01810 (12)	0.00849 (11)	−0.00294 (9)	0.00026 (8)	0.00018 (7)
Re2	0.03762 (15)	0.01828 (12)	0.00805 (11)	−0.00136 (9)	−0.00146 (8)	−0.00093 (7)
O21	0.052 (3)	0.028 (2)	0.018 (2)	0.010 (2)	0.0100 (19)	0.0049 (18)
O22	0.050 (3)	0.032 (3)	0.025 (2)	0.004 (2)	−0.011 (2)	0.004 (2)
O12	0.044 (3)	0.028 (2)	0.022 (2)	0.005 (2)	0.0111 (19)	0.0002 (19)
C21	0.031 (3)	0.008 (2)	0.009 (2)	−0.001 (2)	−0.002 (2)	0.0019 (18)
C12	0.050 (3)	0.041 (3)	0.028 (3)	0.004 (2)	0.001 (2)	0.002 (2)
C22	0.034 (3)	0.018 (3)	0.015 (3)	0.002 (2)	−0.003 (2)	−0.004 (2)
O13	0.060 (3)	0.028 (2)	0.028 (2)	−0.020 (2)	0.004 (2)	−0.002 (2)
O23	0.053 (3)	0.028 (2)	0.023 (2)	−0.013 (2)	−0.003 (2)	−0.0039 (19)
C13	0.037 (4)	0.029 (3)	0.013 (3)	−0.005 (3)	−0.001 (2)	−0.006 (2)
C23	0.033 (3)	0.027 (3)	0.009 (2)	0.003 (3)	0.001 (2)	0.000 (2)
O1	0.034 (2)	0.0147 (18)	0.0113 (17)	0.0002 (17)	0.0006 (15)	0.0012 (14)
O2	0.031 (2)	0.034 (2)	0.014 (2)	0.0017 (19)	0.0014 (16)	−0.0003 (17)
C1	0.040 (4)	0.019 (3)	0.025 (3)	0.002 (3)	0.001 (3)	0.003 (2)
C11	0.032 (3)	0.015 (3)	0.014 (2)	−0.004 (2)	0.000 (2)	−0.003 (2)
O11	0.043 (3)	0.024 (2)	0.022 (2)	0.0000 (19)	−0.0074 (19)	0.0003 (17)
O31	0.049 (3)	0.024 (2)	0.0098 (18)	0.001 (2)	0.0006 (18)	0.0023 (16)
N1	0.044 (3)	0.018 (2)	0.007 (2)	−0.003 (2)	0.0014 (19)	−0.0002 (17)
N3	0.044 (3)	0.018 (2)	0.007 (2)	−0.004 (2)	−0.0002 (19)	−0.0021 (17)
N2	0.059 (4)	0.018 (2)	0.009 (2)	−0.008 (2)	0.006 (2)	−0.0010 (18)
C33	0.039 (3)	0.018 (3)	0.011 (2)	0.000 (2)	0.003 (2)	0.000 (2)
C31	0.044 (4)	0.015 (3)	0.013 (2)	0.002 (2)	0.003 (2)	0.002 (2)
C34	0.055 (4)	0.016 (3)	0.014 (3)	−0.006 (3)	0.002 (3)	−0.002 (2)
C32	0.060 (5)	0.015 (3)	0.011 (3)	−0.005 (3)	0.002 (3)	0.002 (2)
C2	0.050 (3)	0.041 (3)	0.028 (3)	0.004 (2)	0.001 (2)	0.002 (2)

Geometric parameters (Å, º) top

Re1—C11	1.886 (6)	C1—H1A	0.96
Re1—C13	1.908 (7)	C1—H1B	0.96
Re1—C12	1.918 (8)	C11—O11	1.161 (7)
Re1—O2	2.149 (4)	O31—C31	1.225 (7)
Re1—N3	2.150 (5)	N1—C31	1.367 (7)
Re1—O1	2.153 (4)	N1—C33	1.399 (7)
Re2—C21	1.849 (5)	N3—C33	1.300 (7)
Re2—C22	1.935 (6)	N3—H3	0.92 (8)
Re2—C23	1.949 (6)	N2—C33	1.353 (8)
Re2—O2	2.065 (4)	N2—C34	1.442 (7)
Re2—O1	2.073 (4)	N2—C32	1.449 (7)
Re2—N1	2.136 (5)	C31—C32	1.507 (8)
O21—C21	1.159 (7)	C34—H34C	0.96
O22—C22	1.143 (7)	C34—H34B	0.96
O12—C12	1.147 (9)	C34—H34A	0.96
O13—C13	1.165 (8)	C32—H32A	0.97
O23—C23	1.137 (8)	C32—H32B	0.97
O1—C1	1.426 (7)	C2—H2B	0.96
O2—C2	1.464 (10)	C2—H2A	0.96
C1—H1C	0.96	C2—H2C	0.96

C11—Re1—C13	86.7 (3)	C2—O2—Re1	118.1 (4)
C11—Re1—C12	86.0 (3)	Re2—O2—Re1	104.4 (2)
C13—Re1—C12	89.2 (3)	O1—C1—H1C	109.5
C11—Re1—O2	172.7 (2)	O1—C1—H1A	109.5
C13—Re1—O2	96.8 (2)	H1C—C1—H1A	109.5
C12—Re1—O2	100.5 (3)	O1—C1—H1B	109.5
C11—Re1—N3	94.3 (2)	H1C—C1—H1B	109.5
C13—Re1—N3	177.2 (2)	H1A—C1—H1B	109.5
C12—Re1—N3	93.4 (3)	O11—C11—Re1	178.7 (5)
O2—Re1—N3	82.02 (18)	C31—N1—C33	108.2 (5)
C11—Re1—O1	99.6 (2)	C31—N1—Re2	122.5 (4)
C13—Re1—O1	94.8 (2)	C33—N1—Re2	129.1 (4)
C12—Re1—O1	173.3 (2)	C33—N3—Re1	132.9 (4)
O2—Re1—O1	73.71 (16)	C33—N3—H3	111 (5)
N3—Re1—O1	82.47 (17)	Re1—N3—H3	115 (5)
C21—Re2—C22	88.2 (2)	C33—N2—C34	124.4 (5)
C21—Re2—C23	90.4 (2)	C33—N2—C32	109.7 (5)
C22—Re2—C23	89.8 (2)	C34—N2—C32	121.7 (5)
C21—Re2—O2	174.2 (2)	N3—C33—N2	125.9 (5)
C22—Re2—O2	97.3 (2)	N3—C33—N1	123.7 (5)
C23—Re2—O2	91.6 (2)	N2—C33—N1	110.5 (5)
C21—Re2—O1	97.3 (2)	O31—C31—N1	126.1 (6)
C22—Re2—O1	173.2 (2)	O31—C31—C32	125.1 (5)
C23—Re2—O1	94.2 (2)	N1—C31—C32	108.7 (5)
O2—Re2—O1	77.16 (17)	N2—C34—H34C	109.5
C21—Re2—N1	93.8 (2)	N2—C34—H34B	109.5
C22—Re2—N1	92.0 (2)	H34C—C34—H34B	109.5
C23—Re2—N1	175.5 (2)	N2—C34—H34A	109.5
O2—Re2—N1	84.11 (19)	H34C—C34—H34A	109.5
O1—Re2—N1	83.59 (17)	H34B—C34—H34A	109.5
O21—C21—Re2	179.1 (5)	N2—C32—C31	102.3 (5)
O12—C12—Re1	177.1 (7)	N2—C32—H32A	111.3
O22—C22—Re2	177.5 (6)	C31—C32—H32A	111.3
O13—C13—Re1	176.2 (6)	N2—C32—H32B	111.3
O23—C23—Re2	179.4 (6)	C31—C32—H32B	111.3
C1—O1—Re2	119.3 (3)	H32A—C32—H32B	109.2
C1—O1—Re1	118.8 (3)	O2—C2—H2B	109.5
Re2—O1—Re1	104.01 (18)	O2—C2—H2A	109.5
C2—O2—Re2	122.5 (4)	O2—C2—H2C	109.5

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3···O31ⁱ	0.92 (8)	2.17 (8)	3.061 (6)	162 (7)
C2—H2B···O13ⁱⁱ	0.96	2.54	3.453 (9)	159
C2—H2C···O23ⁱⁱ	0.96	2.61	3.504 (9)	154
C34—H34A···O31ⁱ	0.96	2.44	3.332 (7)	155

Symmetry codes: (i) x, −y+2, z+1/2; (ii) −x+1/2, y+1/2, z.

Experimental details

Crystal data
Chemical formula	[Re₂(CH₃O)₂(CO)₆(C₄H₆N₃O)]
M_r	714.67
Crystal system, space group	Orthorhombic, Pbcn
Temperature (K)	100
a, b, c (Å)	24.066 (2), 10.0715 (8), 14.5969 (11)
V (Å³)	3538.1 (5)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	13.73
Crystal size (mm)	0.25 × 0.15 × 0.10

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2008)
T_min, T_max	0.174, 0.371
No. of measured, independent and observed [I > 2σ(I)] reflections	46753, 4276, 3920
R_int	0.050
(sin θ/λ)_max (Å⁻¹)	0.661

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.03, 0.078, 1.16
No. of reflections	4269
No. of parameters	236
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
	w = 1/[σ²(F_o²) + (0.0246P)² + 32.0137P] where P = (F_o² + 2F_c²)/3
Δρ_max, Δρ_min (e Å⁻³)	2.32, −2.30

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

Selected bond lengths (Å) top

Re1—C11	1.886 (6)	Re2—C21	1.849 (5)
Re1—C13	1.908 (7)	Re2—C22	1.935 (6)
Re1—C12	1.918 (8)	Re2—C23	1.949 (6)
Re1—O2	2.149 (4)	Re2—O2	2.065 (4)
Re1—N3	2.150 (5)	Re2—O1	2.073 (4)
Re1—O1	2.153 (4)	Re2—N1	2.136 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3···O31ⁱ	0.92 (8)	2.17 (8)	3.061 (6)	162 (7)
C2—H2B···O13ⁱⁱ	0.96	2.54	3.453 (9)	159
C2—H2C···O23ⁱⁱ	0.96	2.61	3.504 (9)	154
C34—H34A···O31ⁱ	0.96	2.44	3.332 (7)	155

Symmetry codes: (i) x, −y+2, z+1/2; (ii) −x+1/2, y+1/2, z.

Acknowledgements

Leo Kirsten is thanked for the data collection. The University of the Free State, the Department of Chemistry, the NRF and Sasol Ltd are gratefully acknowledged for funding.

References

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