[Bis(pyridin-2-ylmeth­yl)amine-κ3N,N′,N′′]tricarbonyl­rhenium(I) bromide hemihydrate

Schutte, M.; Muller, T.J.; Visser, H.G.; Roodt, A.

doi:10.1107/S1600536812019654

metal-organic compounds

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ISSN: 2056-9890

Volume 68| Part 6| June 2012| Pages m741-m742

doi:10.1107/S1600536812019654

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[Bis(pyridin-2-ylmethyl)amine-κ³N,N′,N′′]tricarbonylrhenium(I) bromide hemihydrate

Marietjie Schutte,^a ^* Theunis J. Muller,^a Hendrik G. Visser ^a and Andreas Roodt ^a

^aDepartment of Chemistry, PO Box 339, University of the Free State, Bloemfontein 9330, South Africa
^*Correspondence e-mail: schuttem@ufs.ac.za

(Received 26 April 2012; accepted 2 May 2012; online 5 May 2012)

The title compound, fac-[Re(C₁₂H₁₂N₃)(CO)₃]Br·0.5H₂O, crystallizes with a cationic rhenium(I) unit, a bromide ion and half a water molecule, situated on a twofold rotation axis, in the asymmetric unit. The Re^I atom is facially surrounded by three carbonyl ligands and a tridentate bis(pyridin-2-ylmethyl)amine ligand in a distorted octahedral environment. N—H⋯Br, O—H⋯Br, C—H⋯O and C—H⋯Br hydrogen bonds are present in the crystal structure and π–π stacking is also observed [centroid–centroid distances = 3.669 (1) Å and 4.054 (1) Å], giving rise to a three-dimentional network. The molecules pack in a head-to-head fashion along the ac plane.

Related literature

For the synthesis of the fac-Re^I-tricarbonyl synthon, see: Alberto et al. (1996 ). For a similar structure, see: Banerjee et al. (2002 ). For related structures, see: Raszeja et al. (2011 ); Banerjee & Zubieta (2005 ); Banerjee et al. (2004 , 2006 ); Kunz et al. (2007 ); Wei et al. (2006 ); Moore et al. (2010 ).

Experimental

Crystal data

[Re(C₁₂H₁₂N₃)(CO)₃]Br·0.5H₂O
M_r = 558.4
Monoclinic, C 2/c
a = 21.542 (5) Å
b = 11.684 (5) Å
c = 15.126 (5) Å
β = 118.172 (5)°
V = 3356 (2) Å³
Z = 8
Mo Kα radiation
μ = 9.64 mm⁻¹
T = 100 K
0.34 × 0.12 × 0.09 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2008 ) T_min = 0.265, T_max = 0.432
28139 measured reflections
4032 independent reflections
3688 reflections with I > 2σ(I)
R_int = 0.031

Refinement

R[F² > 2σ(F²)] = 0.014
wR(F²) = 0.031
S = 1.05
4032 reflections
220 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 1.14 e Å⁻³
Δρ_min = −0.60 e Å⁻³

Table 1
Selected bond lengths (Å)

Re1—C1	1.918 (2)
Re1—C2	1.921 (2)
Re1—C3	1.928 (2)
Re1—N1	2.1819 (19)
Re1—N2	2.1906 (18)
Re1—N3	2.2104 (19)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3⋯Br1	0.85 (2)	2.50 (2)	3.340 (2)	170 (3)
O4—H4A⋯Br1	0.94 (2)	2.31 (2)	3.2429 (18)	171 (3)
C11—H11⋯O2ⁱ	0.93	2.57	3.023 (3)	111
C12—H12⋯O1ⁱⁱ	0.93	2.57	3.285 (3)	134
C21—H21⋯O2ⁱ	0.93	2.56	3.193 (3)	125
C26—H26A⋯Br1ⁱⁱⁱ	0.97	2.88	3.767 (3)	153
C26—H26B⋯O4	0.97	2.31	3.221 (3)	156
Symmetry codes: (i) $[-x+{\script{3\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) $[x, -y, z+{\script{1\over 2}}]$ ; (iii) -x+2, -y+1, -z+1.

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/S1600536812019654/ru2033sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812019654/ru2033Isup2.hkl

checkCIF report

Comment top

N,N-Bis(2-pyridylmethyl)₂aminetricarbonylrhenium(I)bromidehydrate crystallized in the monoclinc spacegroup with the cationic fac- [Re(CO)₃({2-pyridyl-CH₂}₂NH)], bromide anion and half a water molecule in the assymetric unit. The tridentate ligand, N,N-(2-pyridylmethyl)₂amine, coordinate facially to the Re^I core and the other three positions are occupied by carbonyl ligands. The oxygen atom in the water molecule occupies a special position on a mirror plane (Wyckoff position 4e, site symmetry 2). Seven hydrogen bonds (N—H···Br, O—H···Br, C—H···O, C—H···Br) are observed in the crystal structure. Some weak π–π stacking, with a centroid-to-centroid distance of 3.669 (1) Å and 4.054 (1) Å, is also observed between the different pyridine rings of the ligand system. These interactions complete a three dimensional polymericnetwork formed between the Re^I units. Overall, the bond distances and angles compare well with the similar structure reported by Banerjee et al. (2002), N,N-bis(2-pyridylmethyl)₂aminetricarbonylrhenium(I)bromide, that crystallized in the tetragonal P4₁ spacegroup. The three Rhenium to carbonyl distances ranging from 1.918 (2) Å to 1.928 (2) Å compare well to similar structures (Raszeja et al. (2011), Banerjee et al. (2004), Kunz et al. (2007), Wei et al. (2006), Banerjee et al. (2005), Banerjee et al. (2006), Moore et al. (2010)) and also to the N,N-Bis(2-pyridylmethyl)₂aminetricarbonylrhenium(I)bromide structure reported by Banerjee et al. (2002) of 1.901 (6) Å to 1.926 (7) Å. The Re-amine distance of 2.210 (2) Å and the Re-pyridine distances of 2.182 (2) Å and 2.191 (2) Å are slightly longer than the Re-Amine distance of 2.187 (4) Å and the Re-pyridine distances of 2.177 (5) Å and 2.183 (5) Å reported by Banerjee et al. (2002).

Related literature top

For the synthesis of the fac-Re^I-tricarbonyl synthon, see: Alberto et al. (1996). For a similar structure, see: Banerjee et al. (2002). For related structures, see: Raszeja et al. (2011); Banerjee & Zubieta (2005); Banerjee et al. (2004, 2006); Kunz et al. (2007); Wei et al. (2006); Moore et al. (2010).

Experimental top

[NEt₄]₂[Re(CO)₃Br₃] (75 mg, 0.097 mmol), as prepared by Alberto et al. (1996), was dissolved in 20 ml of water, acidified with HNO₃ to pH 2.2. Silver nitrate (50 mg, 0.291 mmol) was added to the solution and stirred for 24 h at room temperature. The grey silver bromide precipitate was filtered off, N,N-bis(2-pyridylmethyl)amine (19.4 mg, 0.100 mmol) was added to the filtrate and stirred overnight at room temperature. The colourless crystals were grown from the filtrate by slow evaporation.

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 of the title compound in the unit cell and the observed π-π stacking in the crystal structure, indicated by dashed lines (hydrogen atoms omitted for clarity).

[Bis(pyridin-2-ylmethyl)amine- κ³N,N',N'']tricarbonylrhenium(I) bromide monohydrate top

Crystal data top

[Re(C₁₂H₁₂N₃)(CO)₃]Br·0.5H₂O	F(000) = 2104
M_r = 558.4	D_x = 2.21 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 21.542 (5) Å	Cell parameters from 9928 reflections
b = 11.684 (5) Å	θ = 2.8–28.3°
c = 15.126 (5) Å	µ = 9.64 mm⁻¹
β = 118.172 (5)°	T = 100 K
V = 3356 (2) Å³	Needle, colourless
Z = 8	0.34 × 0.12 × 0.09 mm

Data collection top

Bruker APEXII CCD diffractometer	3688 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.031
ϕ and ω scans	θ_max = 28°, θ_min = 3.2°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −28→28
T_min = 0.265, T_max = 0.432	k = −15→15
28139 measured reflections	l = −19→17
4032 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)] = 0.014	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.031	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ²(F_o²) + (0.0112P)² + 4.244P] where P = (F_o² + 2F_c²)/3
4032 reflections	(Δ/σ)_max = 0.004
220 parameters	Δρ_max = 1.14 e Å⁻³
2 restraints	Δρ_min = −0.60 e Å⁻³

Crystal data top

[Re(C₁₂H₁₂N₃)(CO)₃]Br·0.5H₂O	V = 3356 (2) Å³
M_r = 558.4	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 21.542 (5) Å	µ = 9.64 mm⁻¹
b = 11.684 (5) Å	T = 100 K
c = 15.126 (5) Å	0.34 × 0.12 × 0.09 mm
β = 118.172 (5)°

Data collection top

Bruker APEXII CCD diffractometer	4032 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2008)	3688 reflections with I > 2σ(I)
T_min = 0.265, T_max = 0.432	R_int = 0.031
28139 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.014	2 restraints
wR(F²) = 0.031	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	Δρ_max = 1.14 e Å⁻³
4032 reflections	Δρ_min = −0.60 e Å⁻³
220 parameters

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	0.832406 (4)	0.266160 (7)	0.262052 (6)	0.01016 (3)
N1	0.82258 (9)	0.22093 (15)	0.39486 (13)	0.0105 (4)
C3	0.84911 (12)	0.3216 (2)	0.15505 (17)	0.0181 (5)
N3	0.91084 (10)	0.37861 (16)	0.37892 (14)	0.0130 (4)
C2	0.74889 (12)	0.35874 (19)	0.21078 (16)	0.0144 (5)
N2	0.92780 (9)	0.16093 (16)	0.33122 (13)	0.0124 (4)
C25	0.98776 (12)	0.21485 (19)	0.39603 (16)	0.0134 (4)
C21	0.92998 (12)	0.04661 (19)	0.31905 (16)	0.0152 (5)
H21	0.8888	0.0093	0.2746	0.018*
C22	0.99066 (12)	−0.0171 (2)	0.36981 (18)	0.0204 (5)
H22	0.9908	−0.0954	0.3586	0.024*
C24	1.05014 (12)	0.1556 (2)	0.45125 (17)	0.0185 (5)
H24	1.0906	0.194	0.4966	0.022*
C23	1.05138 (12)	0.0382 (2)	0.43790 (18)	0.0210 (5)
H23	1.0927	−0.0029	0.4744	0.025*
C15	0.86452 (11)	0.27820 (18)	0.48059 (16)	0.0125 (4)
C11	0.78009 (11)	0.13816 (19)	0.39807 (16)	0.0139 (4)
H11	0.7496	0.1013	0.3388	0.017*
C12	0.78005 (12)	0.1058 (2)	0.48615 (17)	0.0164 (5)
H12	0.7504	0.048	0.486	0.02*
C16	0.90207 (12)	0.3815 (2)	0.47098 (16)	0.0157 (5)
H16A	0.8758	0.4496	0.4695	0.019*
H16B	0.9481	0.3865	0.5294	0.019*
O2	0.69748 (8)	0.41059 (14)	0.17770 (13)	0.0210 (4)
O1	0.74405 (8)	0.07008 (14)	0.12519 (12)	0.0212 (4)
O3	0.85788 (9)	0.35753 (17)	0.09110 (13)	0.0306 (4)
C1	0.77537 (11)	0.1458 (2)	0.17563 (16)	0.0147 (5)
C26	0.98272 (11)	0.34246 (19)	0.39980 (17)	0.0151 (5)
H26A	1.0168	0.3697	0.4656	0.018*
H26B	0.994	0.3767	0.3507	0.018*
C14	0.86774 (13)	0.2485 (2)	0.57138 (17)	0.0171 (5)
H14	0.8983	0.2868	0.6298	0.02*
C13	0.82505 (12)	0.1613 (2)	0.57449 (17)	0.0185 (5)
H13	0.8266	0.1404	0.6348	0.022*
Br1	0.899690 (12)	0.65619 (2)	0.320564 (16)	0.01760 (5)
O4	1	0.5200 (3)	0.25	0.0578 (10)
H3	0.9062 (16)	0.4465 (17)	0.356 (2)	0.053 (7)*
H4A	0.9723 (15)	0.567 (2)	0.268 (2)	0.053 (7)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Re1	0.00954 (5)	0.01156 (5)	0.00819 (4)	0.00126 (3)	0.00319 (3)	0.00068 (3)
N1	0.0101 (9)	0.0109 (9)	0.0103 (8)	0.0031 (7)	0.0046 (7)	0.0003 (7)
C3	0.0121 (11)	0.0238 (13)	0.0156 (11)	0.0040 (9)	0.0042 (9)	0.0025 (10)
N3	0.0124 (9)	0.0106 (9)	0.0138 (9)	−0.0001 (8)	0.0045 (8)	0.0004 (7)
C2	0.0195 (12)	0.0123 (11)	0.0133 (11)	−0.0026 (9)	0.0093 (9)	0.0000 (9)
N2	0.0114 (9)	0.0143 (10)	0.0125 (9)	0.0016 (7)	0.0063 (7)	0.0016 (7)
C25	0.0133 (11)	0.0162 (12)	0.0126 (10)	0.0005 (9)	0.0077 (9)	0.0004 (8)
C21	0.0143 (11)	0.0174 (12)	0.0154 (11)	0.0015 (9)	0.0082 (9)	−0.0008 (9)
C22	0.0226 (13)	0.0181 (13)	0.0221 (12)	0.0049 (10)	0.0119 (11)	0.0009 (10)
C24	0.0133 (11)	0.0246 (13)	0.0163 (11)	0.0016 (10)	0.0060 (9)	0.0001 (10)
C23	0.0161 (12)	0.0261 (14)	0.0196 (12)	0.0105 (10)	0.0073 (10)	0.0037 (10)
C15	0.0100 (10)	0.0127 (11)	0.0137 (10)	0.0038 (8)	0.0049 (9)	−0.0008 (8)
C11	0.0134 (11)	0.0112 (11)	0.0161 (11)	0.0040 (9)	0.0061 (9)	0.0009 (9)
C12	0.0176 (12)	0.0145 (12)	0.0216 (12)	0.0044 (9)	0.0129 (10)	0.0052 (9)
C16	0.0150 (11)	0.0167 (12)	0.0129 (10)	−0.0014 (9)	0.0044 (9)	−0.0046 (9)
O2	0.0154 (9)	0.0152 (9)	0.0295 (9)	0.0036 (7)	0.0081 (7)	0.0045 (7)
O1	0.0191 (9)	0.0223 (9)	0.0174 (8)	−0.0003 (7)	0.0047 (7)	−0.0083 (7)
O3	0.0287 (10)	0.0461 (12)	0.0224 (9)	0.0075 (9)	0.0166 (8)	0.0134 (9)
C1	0.0124 (11)	0.0191 (12)	0.0120 (10)	0.0050 (9)	0.0053 (9)	0.0023 (9)
C26	0.0100 (11)	0.0169 (12)	0.0171 (11)	−0.0013 (9)	0.0053 (9)	−0.0004 (9)
C14	0.0182 (12)	0.0196 (13)	0.0121 (11)	0.0068 (9)	0.0061 (10)	−0.0014 (9)
C13	0.0197 (12)	0.0205 (13)	0.0179 (12)	0.0096 (10)	0.0110 (10)	0.0071 (9)
Br1	0.01889 (12)	0.01679 (12)	0.01454 (11)	0.00078 (9)	0.00578 (9)	0.00349 (8)
O4	0.091 (3)	0.0332 (19)	0.090 (3)	0	0.076 (2)	0

Geometric parameters (Å, º) top

Re1—C1	1.918 (2)	C22—H22	0.93
Re1—C2	1.921 (2)	C24—C23	1.388 (3)
Re1—C3	1.928 (2)	C24—H24	0.93
Re1—N1	2.1819 (19)	C23—H23	0.93
Re1—N2	2.1906 (18)	C15—C14	1.386 (3)
Re1—N3	2.2104 (19)	C15—C16	1.498 (3)
N1—C11	1.348 (3)	C11—C12	1.385 (3)
N1—C15	1.356 (3)	C11—H11	0.93
C3—O3	1.149 (3)	C12—C13	1.386 (3)
N3—C26	1.488 (3)	C12—H12	0.93
N3—C16	1.491 (3)	C16—H16A	0.97
N3—H3	0.850 (18)	C16—H16B	0.97
C2—O2	1.149 (3)	O1—C1	1.155 (3)
N2—C21	1.352 (3)	C26—H26A	0.97
N2—C25	1.353 (3)	C26—H26B	0.97
C25—C24	1.387 (3)	C14—C13	1.389 (3)
C25—C26	1.498 (3)	C14—H14	0.93
C21—C22	1.380 (3)	C13—H13	0.93
C21—H21	0.93	O4—H4A	0.939 (17)
C22—C23	1.385 (3)

C1—Re1—C2	87.77 (10)	C21—C22—H22	120.8
C1—Re1—C3	89.29 (10)	C23—C22—H22	120.8
C2—Re1—C3	88.99 (9)	C25—C24—C23	119.0 (2)
C1—Re1—N1	98.08 (8)	C25—C24—H24	120.5
C2—Re1—N1	91.64 (8)	C23—C24—H24	120.5
C3—Re1—N1	172.62 (8)	C22—C23—C24	119.6 (2)
C1—Re1—N2	93.94 (8)	C22—C23—H23	120.2
C2—Re1—N2	175.80 (8)	C24—C23—H23	120.2
C3—Re1—N2	94.86 (8)	N1—C15—C14	121.6 (2)
N1—Re1—N2	84.33 (7)	N1—C15—C16	116.82 (19)
C1—Re1—N3	169.31 (8)	C14—C15—C16	121.4 (2)
C2—Re1—N3	101.82 (9)	N1—C11—C12	122.6 (2)
C3—Re1—N3	95.54 (9)	N1—C11—H11	118.7
N1—Re1—N3	77.14 (7)	C12—C11—H11	118.7
N2—Re1—N3	76.18 (7)	C11—C12—C13	118.8 (2)
C11—N1—C15	118.46 (19)	C11—C12—H12	120.6
C11—N1—Re1	124.72 (14)	C13—C12—H12	120.6
C15—N1—Re1	116.78 (14)	N3—C16—C15	112.61 (18)
O3—C3—Re1	177.9 (2)	N3—C16—H16A	109.1
C26—N3—C16	112.72 (17)	C15—C16—H16A	109.1
C26—N3—Re1	109.09 (13)	N3—C16—H16B	109.1
C16—N3—Re1	111.98 (13)	C15—C16—H16B	109.1
C26—N3—H3	105 (2)	H16A—C16—H16B	107.8
C16—N3—H3	108 (2)	O1—C1—Re1	176.56 (19)
Re1—N3—H3	109 (2)	N3—C26—C25	111.18 (18)
O2—C2—Re1	177.3 (2)	N3—C26—H26A	109.4
C21—N2—C25	118.42 (19)	C25—C26—H26A	109.4
C21—N2—Re1	125.07 (15)	N3—C26—H26B	109.4
C25—N2—Re1	116.37 (15)	C25—C26—H26B	109.4
N2—C25—C24	121.8 (2)	H26A—C26—H26B	108
N2—C25—C26	115.44 (19)	C15—C14—C13	119.5 (2)
C24—C25—C26	122.7 (2)	C15—C14—H14	120.2
N2—C21—C22	122.8 (2)	C13—C14—H14	120.2
N2—C21—H21	118.6	C12—C13—C14	118.9 (2)
C22—C21—H21	118.6	C12—C13—H13	120.5
C21—C22—C23	118.4 (2)	C14—C13—H13	120.5

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3···Br1	0.85 (2)	2.50 (2)	3.340 (2)	170 (3)
O4—H4A···Br1	0.94 (2)	2.31 (2)	3.2429 (18)	171 (3)
C11—H11···O2ⁱ	0.93	2.57	3.023 (3)	111
C12—H12···O1ⁱⁱ	0.93	2.57	3.285 (3)	134
C21—H21···O2ⁱ	0.93	2.56	3.193 (3)	125
C26—H26A···Br1ⁱⁱⁱ	0.97	2.88	3.767 (3)	153
C26—H26B···O4	0.97	2.31	3.221 (3)	156

Symmetry codes: (i) −x+3/2, y−1/2, −z+1/2; (ii) x, −y, z+1/2; (iii) −x+2, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	[Re(C₁₂H₁₂N₃)(CO)₃]Br·0.5H₂O
M_r	558.4
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	100
a, b, c (Å)	21.542 (5), 11.684 (5), 15.126 (5)
β (°)	118.172 (5)
V (Å³)	3356 (2)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	9.64
Crystal size (mm)	0.34 × 0.12 × 0.09

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2008)
T_min, T_max	0.265, 0.432
No. of measured, independent and observed [I > 2σ(I)] reflections	28139, 4032, 3688
R_int	0.031
(sin θ/λ)_max (Å⁻¹)	0.661

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.014, 0.031, 1.05
No. of reflections	4032
No. of parameters	220
No. of restraints	2
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	1.14, −0.60

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

Selected geometric parameters (Å, º) top

Re1—C1	1.918 (2)	Re1—N1	2.1819 (19)
Re1—C2	1.921 (2)	Re1—N2	2.1906 (18)
Re1—C3	1.928 (2)	Re1—N3	2.2104 (19)

C1—Re1—N1	98.08 (8)	N1—Re1—N2	84.33 (7)
C2—Re1—N1	91.64 (8)	C1—Re1—N3	169.31 (8)
C3—Re1—N1	172.62 (8)	C2—Re1—N3	101.82 (9)
C1—Re1—N2	93.94 (8)	C3—Re1—N3	95.54 (9)
C2—Re1—N2	175.80 (8)	N1—Re1—N3	77.14 (7)
C3—Re1—N2	94.86 (8)	N2—Re1—N3	76.18 (7)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3···Br1	0.850 (18)	2.499 (18)	3.340 (2)	170 (3)
O4—H4A···Br1	0.939 (17)	2.313 (18)	3.2429 (18)	171 (3)
C11—H11···O2ⁱ	0.93	2.57	3.023 (3)	110.6
C12—H12···O1ⁱⁱ	0.93	2.57	3.285 (3)	133.6
C21—H21···O2ⁱ	0.93	2.56	3.193 (3)	125.2
C26—H26A···Br1ⁱⁱⁱ	0.97	2.88	3.767 (3)	152.5
C26—H26B···O4	0.97	2.31	3.221 (3)	156.4

Symmetry codes: (i) −x+3/2, y−1/2, −z+1/2; (ii) x, −y, z+1/2; (iii) −x+2, −y+1, −z+1.

Acknowledgements

We would like to thank the University of the Free State, the Chemistry Department, the NRF and Sasol Ltd for financial support.

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