(μ(1)-Methano-lato-κ(1)O)-μ(1)-methoxo-κ(1)O-(μ(2)-2-amino-1-methyl-5H-imidazol-4-one-κ(2)N:N')-hexa-carbonyl-dirhenium(I).

In the title compound, [Re(2)(CH(3)O)(2)(CO)(6)(C(4)H(6)N(3)O)], 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 octa-hedral geometry around each Re(I) atom. The bridging methanolato and methoxo ligands are bent out of the Re(2)O(2) 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 Re(2)N(2)C 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 mol-ecules 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 ReI 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 ReI complex, see: Schutte et al. (2012a ▶). For similar ReI structures, see: Schutte et al. (2011 ▶, 2012b ▶,c ▶).

Experimental

Crystal data

[Re2(CH3O)2(CO)6(C4H6N3O)]

M = 714.67

Orthorhombic,

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[F 2 > 2σ(F 2)] = 0.030

wR(F 2) = 0.078

S = 1.16

4269 reflections

236 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 2.32 e Å−3

Δρmin = −2.30 e Å−3

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 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812041700/tk5155sup1.cif

Click here for additional data file.

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

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

[Re2(CH3O)2(CO)6(C4H6N3O)]	F(000) = 2616
Mr = 714.67	Dx = 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

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

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(Fo2) + (0.0246P)2 + 32.0137P] where P = (Fo2 + 2Fc2)/3
4269 reflections	(Δ/σ)max = 0.006
236 parameters	Δρmax = 2.32 e Å−3
0 restraints	Δρmin = −2.30 e Å−3

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.

	x	y	z	Uiso*/Ueq
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)*

	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)

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

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

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) ; (ii) .