Tetra­ethyl­ammonium dibromido­tricarbon­yl(o-toluidine)rhenate(I)

Brink, A.; Visser, H.G.; Roodt, A.

doi:10.1107/S1600536810050038

metal-organic compounds

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ISSN: 2056-9890

Volume 67| Part 1| January 2011| Pages m32-m33

https://doi.org/10.1107/S1600536810050038

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Tetraethylammonium dibromidotricarbonyl(o-toluidine)rhenate(I)

Alice Brink,^a ^* Hendrik G. Visser ^a and Andreas Roodt ^a

^aDepartment of Chemistry, University of the Free State, PO Box 339, Bloemfontein 9300, South Africa
^*Correspondence e-mail: alice.brink@gmail.com

(Received 23 November 2010; accepted 30 November 2010; online 4 December 2010)

In the title compound, (C₈H₂₀N)[ReBr₂(C₇H₉N)(CO)₃], the Re^I atom is octahedrally surrounded by three carbonyl ligands orientated in a facial arrangement, two bromide ligands and an o-toluidine ligand. The amine lies trans to the carbonyl ligand and is substitutionally disordered over two positions in a 0.66 (1):0.34 (1) ratio. An array of C—H⋯O, C—H⋯Br and N—H⋯Br hydrogen-bonding interactions between the cations and the surrounding rhenate anions stabilize the crystal structure.

Related literature

For the synthesis of the Re^I–tricarbonyl synthon, see: Alberto et al. (1996 ); Brink et al. (2009 ). For related rhenium–tricarbonyl complexes, see: Mundwiler et al. (2004 ); Wang et al. (2003 ); Saw et al. (2006 ); Schutte et al. (2008 , 2009 , 2010 ); Wei et al. (2003 ); Schibli et al. (2000 ). For kinetic studies of related Re compounds, see: Smith et al. (1996 ); Abou-Hamdan et al. (1998 ). For related dibromido structures, see: Alberto et al. (1999 ); Abram et al. (1998 ).

Experimental

Crystal data

(C₈H₂₀N)[ReBr₂(C₇H₉N)(CO)₃]
M_r = 667.45
Monoclinic, P 2₁ /c
a = 10.776 (2) Å
b = 18.466 (4) Å
c = 11.745 (2) Å
β = 106.74 (3)°
V = 2238.2 (8) Å³
Z = 4
Mo Kα radiation
μ = 9.02 mm⁻¹
T = 100 K
0.42 × 0.32 × 0.08 mm

Data collection

Bruker X8 APEXII 4K Kappa CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2004 ) T_min = 0.116, T_max = 0.532
45095 measured reflections
5371 independent reflections
4411 reflections with I > 2σ(I)
R_int = 0.072

Refinement

R[F² > 2σ(F²)] = 0.032
wR(F²) = 0.086
S = 1.06
5371 reflections
270 parameters
H-atom parameters constrained
Δρ_max = 2.5 e Å⁻³
Δρ_min = −2.99 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1C⋯Br2ⁱ	0.92	2.7	3.542 (4)	153
N1—H1B⋯Br1ⁱ	0.92	2.75	3.594 (4)	153
C121—H12C⋯O03ⁱⁱ	0.98	2.5	3.139 (10)	123
C35—H35B⋯O03ⁱⁱⁱ	0.99	2.39	3.196 (7)	138
C37—H37A⋯Br1^iv	0.99	2.92	3.911 (6)	174
Symmetry codes: (i) -x+2, -y+2, -z+2; (ii) -x+1, -y+2, -z+2; (iii) -x+1, -y+2, -z+1; (iv) $[x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2005 ); cell refinement: SAINT-Plus (Bruker, 2004); data reduction: SAINT-Plus and XPREP (Bruker, 2004); program(s) used to solve structure: SIR92 (Altomare et al., 1999 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ); molecular graphics: DIAMOND (Brandenburg & Putz, 2004 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536810050038/bt5421sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810050038/bt5421Isup2.hkl

checkCIF report

Comment top

The structure forms part of an ongoing investigation aimed at determining the structural and kinetic behaviour of fac-rhenium tricarbonyl complexes. Various rhenium bi- and tridentate tricarbonyl ligands have been synthesized (Mundwiler et al., 2004, Wang et al., 2003, Saw et al., 2006, Schutte et al., 2009, 2008, 2010, Wei et al., 2003, Schibli et al., 2000). A few crystallographic studies on dibromido monodentate rhenium compounds have been reported in literature (Alberto et al., 1999, Abram et al., 1998).

The title complex crystallized as a distorted octahedral anionic Re^I compound with one tetraethylammonium counter ion in the asymmetric unit (Fig. 1). The coordinated amine lies in an axial position below the equatorial plane, defined as Br1—Br2—C02—C03, and trans to a carbonyl ligand. It is disordered over two positions and the plane through the aromatic carbons lies at an angle of 35.2 (2)° to the equatorial plane. The Re—N bond distance (2.241 (4) Å) is longer than for the rhenium acetonitrile analogue (2.150 (6) Å) (Abram et al., 1998).

The longer Re—Br bond lengths (2.6390 (7) Å and 2.6370 (8) Å) are induced by the facially coordinated carbonyl ligands and compares well with related structures (Abram et al., 1998, Schutte et al., 2010). Intermolecular C—H···O, C—H···Br and N—H···Br hydrogen-bonding interactions are observed between rhenate anions and neighboring cations.

Related literature top

For the synthesis of the Re^I–tricarbonyl synthon, see: Alberto et al. (1996); Brink et al. (2009). For related rhenium–tricarbonyl complexes, see: Mundwiler et al. (2004); Wang et al. (2003); Saw et al. (2006); Schutte et al. (2008, 2009, 2010); Wei et al. (2003); Schibli et al. (2000). For related rhenium kinetic studies, see: Smith et al. (1996); Abou-Hamdan et al. (1998). For related dibromido structures, see: Alberto et al. (1999); Abram et al. (1998).

Experimental top

[NEt₄]₂[Re(CO)₃Br₃] (0.13 mmol) (synthesized according to Alberto et al. (1996)) was dissolved in 6 ml methanol. The ligand 2-(o-tolyliminomethyl)phenol (0.14 mmol) (for related synthesis see Brink et al., 2009), containing 10% o-toluidine as byproduct, was dissolved in 6 ml MeOH and slowly added. The reaction mixture was stirred for 2 h at room temperature. Crystals of the title complex whereby the Re bonded preferentially to the amine were obtained by the slow evaporation of the solvent at 4°C.

Structure description top

For the synthesis of the Re^I–tricarbonyl synthon, see: Alberto et al. (1996); Brink et al. (2009). For related rhenium–tricarbonyl complexes, see: Mundwiler et al. (2004); Wang et al. (2003); Saw et al. (2006); Schutte et al. (2008, 2009, 2010); Wei et al. (2003); Schibli et al. (2000). For related rhenium kinetic studies, see: Smith et al. (1996); Abou-Hamdan et al. (1998). For related dibromido structures, see: Alberto et al. (1999); Abram et al. (1998).

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT-Plus (Bruker, 2004); data reduction: SAINT-Plus and XPREP (Bruker, 2004); program(s) used to solve structure: SIR92 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg & Putz, 2004); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top

	Fig. 1. Representation of the molecular structure of the title compound, showing the numbering scheme and displacement ellipsoids drawn at 50% probability level. Hydrogen atoms are omitted for clarity.
	Fig. 2. Representation of the hydrogen-bonding interactions (only one complete molecular structure (symm. op.: x, y, z) is shown).

Tetraethylammonium dibromidotricarbonyl(o-toluidine)rhenate(I) top

Crystal data top

(C₈H₂₀N)[ReBr₂(C₇H₉N)(CO)₃]	F(000) = 1280
M_r = 667.45	D_x = 1.981 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 9885 reflections
a = 10.776 (2) Å	θ = 3.2–28.3°
b = 18.466 (4) Å	µ = 9.02 mm⁻¹
c = 11.745 (2) Å	T = 100 K
β = 106.74 (3)°	Plate, yellow
V = 2238.2 (8) Å³	0.42 × 0.32 × 0.08 mm
Z = 4

Data collection top

Bruker X8 APEXII 4K Kappa CCD diffractometer	5371 independent reflections
Radiation source: sealed tube	4411 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.072
Detector resolution: 512 pixels mm^-1	θ_max = 28°, θ_min = 3.2°
ω and φ scans	h = −14→13
Absorption correction: multi-scan (SADABS; Bruker, 2004)	k = −24→24
T_min = 0.116, T_max = 0.532	l = −15→15
45095 measured reflections

Refinement top

Refinement on F²	0 restraints
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.032	w = 1/[σ²(F_o²) + (0.0446P)² + 2.6175P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.086	(Δ/σ)_max = 0.001
S = 1.06	Δρ_max = 2.5 e Å⁻³
5371 reflections	Δρ_min = −2.99 e Å⁻³
270 parameters

Crystal data top

(C₈H₂₀N)[ReBr₂(C₇H₉N)(CO)₃]	V = 2238.2 (8) Å³
M_r = 667.45	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 10.776 (2) Å	µ = 9.02 mm⁻¹
b = 18.466 (4) Å	T = 100 K
c = 11.745 (2) Å	0.42 × 0.32 × 0.08 mm
β = 106.74 (3)°

Data collection top

Bruker X8 APEXII 4K Kappa CCD diffractometer	5371 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2004)	4411 reflections with I > 2σ(I)
T_min = 0.116, T_max = 0.532	R_int = 0.072
45095 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.032	0 restraints
wR(F²) = 0.086	H-atom parameters constrained
S = 1.06	Δρ_max = 2.5 e Å⁻³
5371 reflections	Δρ_min = −2.99 e Å⁻³
270 parameters

Special details top

Experimental. The intensity data was collected on a Bruker X8 Apex II 4 K Kappa CCD diffractometer using an exposure time of 30 s/frame. A total of 1977 frames were collected with a frame width of 0.5° covering up to θ = 28.0° with 99.4% completeness accomplished

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	Occ. (<1)
Re1	0.735442 (18)	0.985810 (11)	0.808028 (15)	0.01480 (7)
Br1	0.81038 (5)	0.89501 (3)	0.98836 (4)	0.01871 (12)
Br2	0.95834 (5)	0.96560 (3)	0.76184 (4)	0.01895 (12)
N1	0.8495 (4)	1.0651 (2)	0.9422 (3)	0.0174 (9)
H1A	0.8563	1.0468	1.0166	0.021*	0.659 (10)
H1B	0.932	1.0671	0.9343	0.021*	0.659 (10)
H1C	0.888	1.0409	1.0119	0.021*	0.341 (10)
H1D	0.9145	1.0842	0.9148	0.021*	0.341 (10)
N2	0.8171 (4)	0.8488 (2)	0.3722 (3)	0.0165 (8)
O01	0.6021 (4)	0.8662 (2)	0.6363 (3)	0.0324 (10)
O02	0.6462 (4)	1.0930 (2)	0.6027 (3)	0.0294 (9)
O03	0.4809 (4)	1.0153 (2)	0.8640 (4)	0.0363 (11)
C01	0.6523 (5)	0.9121 (3)	0.7010 (4)	0.0208 (11)
C02	0.6823 (5)	1.0544 (3)	0.6816 (4)	0.0211 (11)
C03	0.5790 (5)	1.0036 (3)	0.8445 (5)	0.0227 (11)
C11	0.8014 (8)	1.1388 (5)	0.9379 (8)	0.0200 (19)	0.659 (10)
C12	0.7270 (8)	1.1603 (5)	1.0104 (7)	0.022 (2)	0.659 (10)
C13	0.6778 (8)	1.2305 (5)	0.9964 (9)	0.025 (2)	0.659 (10)
H13	0.627	1.2465	1.0456	0.03*	0.659 (10)
C14	0.7005 (8)	1.2773 (6)	0.9139 (8)	0.025 (2)	0.659 (10)
H14	0.6648	1.3247	0.9058	0.03*	0.659 (10)
C15	0.7754 (8)	1.2551 (5)	0.8425 (7)	0.025 (2)	0.659 (10)
H15	0.7924	1.2871	0.7854	0.03*	0.659 (10)
C16	0.8250 (9)	1.1859 (6)	0.8557 (8)	0.023 (2)	0.659 (10)
H16	0.8766	1.1703	0.807	0.027*	0.659 (10)
C121	0.7031 (9)	1.1098 (5)	1.1036 (9)	0.032 (2)	0.659 (10)
H12A	0.638	1.1311	1.1371	0.048*	0.659 (10)
H12B	0.7841	1.1025	1.167	0.048*	0.659 (10)
H12C	0.6717	1.0631	1.0669	0.048*	0.659 (10)
C25	0.6163 (16)	1.1668 (10)	1.0700 (14)	0.029 (4)*	0.341 (10)
H25	0.5649	1.1593	1.1224	0.035*	0.341 (10)
C22	0.7679 (15)	1.1900 (9)	0.9138 (13)	0.021 (4)*	0.341 (10)
C24	0.615 (2)	1.2320 (11)	1.0160 (16)	0.032 (4)*	0.341 (10)
H24	0.5629	1.2698	1.0328	0.039*	0.341 (10)
C23	0.6844 (18)	1.2448 (12)	0.9392 (19)	0.020 (4)*	0.341 (10)
H23	0.6782	1.2906	0.9013	0.025*	0.341 (10)
C21	0.7704 (18)	1.1241 (11)	0.9674 (16)	0.020 (5)*	0.341 (10)
C26	0.6933 (16)	1.1111 (10)	1.0483 (16)	0.019 (4)*	0.341 (10)
H26	0.6955	1.0653	1.0859	0.023*	0.341 (10)
C221	0.8433 (19)	1.2027 (11)	0.8293 (17)	0.018 (5)*	0.341 (10)
H22A	0.8303	1.2526	0.8002	0.027*	0.341 (10)
H22B	0.8145	1.1692	0.7622	0.027*	0.341 (10)
H22C	0.9355	1.1947	0.8694	0.027*	0.341 (10)
C31	0.8711 (5)	0.8176 (3)	0.2768 (4)	0.0240 (11)
H31A	0.8	0.8148	0.2015	0.029*
H31B	0.937	0.8514	0.2639	0.029*
C32	0.9320 (6)	0.7433 (3)	0.3040 (5)	0.0321 (14)
H32A	0.9594	0.7263	0.2359	0.048*
H32B	0.8686	0.7095	0.3192	0.048*
H32C	1.0075	0.7462	0.3743	0.048*
C33	0.9209 (5)	0.8507 (3)	0.4913 (4)	0.0215 (11)
H33A	0.8832	0.8725	0.5508	0.026*
H33B	0.9455	0.8003	0.5165	0.026*
C34	1.0420 (5)	0.8920 (4)	0.4925 (5)	0.0336 (14)
H34A	1.0957	0.8983	0.5748	0.05*
H34B	1.0181	0.9396	0.4558	0.05*
H34C	1.0907	0.865	0.4478	0.05*
C35	0.7702 (5)	0.9248 (3)	0.3309 (4)	0.0217 (11)
H35A	0.8448	0.9532	0.3222	0.026*
H35B	0.7065	0.9212	0.2513	0.026*
C36	0.7084 (6)	0.9660 (3)	0.4118 (5)	0.0281 (12)
H36A	0.6865	1.0151	0.3807	0.042*
H36B	0.7693	0.9687	0.4918	0.042*
H36C	0.6294	0.941	0.4153	0.042*
C37	0.7062 (5)	0.8034 (3)	0.3888 (5)	0.0249 (12)
H37A	0.7392	0.7541	0.4133	0.03*
H37B	0.6777	0.8244	0.4546	0.03*
C38	0.5894 (6)	0.7972 (3)	0.2804 (6)	0.0370 (15)
H38A	0.5259	0.7642	0.2977	0.056*
H38B	0.6167	0.7782	0.2134	0.056*
H38C	0.5502	0.8451	0.2599	0.056*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Re1	0.01788 (12)	0.01279 (12)	0.01337 (10)	−0.00031 (8)	0.00393 (8)	0.00151 (7)
Br1	0.0253 (3)	0.0146 (2)	0.0156 (2)	−0.0011 (2)	0.00488 (19)	0.00306 (17)
Br2	0.0216 (3)	0.0210 (3)	0.0157 (2)	−0.0011 (2)	0.00766 (19)	−0.00174 (18)
N1	0.023 (2)	0.012 (2)	0.0162 (19)	−0.0010 (17)	0.0056 (16)	0.0001 (15)
N2	0.021 (2)	0.015 (2)	0.0133 (18)	0.0006 (17)	0.0048 (16)	0.0014 (15)
O01	0.041 (2)	0.025 (2)	0.026 (2)	−0.0135 (19)	0.0027 (17)	−0.0051 (17)
O02	0.044 (2)	0.020 (2)	0.0220 (19)	0.0010 (18)	0.0058 (17)	0.0058 (16)
O03	0.025 (2)	0.055 (3)	0.033 (2)	0.008 (2)	0.0136 (18)	0.014 (2)
C01	0.023 (3)	0.018 (3)	0.020 (2)	−0.004 (2)	0.005 (2)	0.008 (2)
C02	0.025 (3)	0.020 (3)	0.019 (2)	−0.001 (2)	0.008 (2)	−0.001 (2)
C03	0.024 (3)	0.022 (3)	0.021 (3)	0.000 (2)	0.006 (2)	0.007 (2)
C11	0.012 (4)	0.027 (5)	0.017 (4)	−0.004 (4)	−0.002 (3)	−0.003 (3)
C12	0.023 (4)	0.020 (4)	0.022 (4)	0.004 (3)	0.005 (3)	−0.005 (3)
C13	0.018 (5)	0.028 (5)	0.029 (5)	0.001 (4)	0.008 (4)	−0.008 (4)
C14	0.023 (5)	0.022 (5)	0.026 (4)	−0.002 (4)	0.001 (3)	−0.004 (4)
C15	0.023 (4)	0.022 (5)	0.026 (4)	−0.006 (4)	−0.002 (3)	0.006 (3)
C16	0.027 (5)	0.028 (5)	0.016 (4)	−0.004 (4)	0.009 (4)	0.000 (4)
C121	0.039 (6)	0.035 (6)	0.026 (5)	−0.006 (4)	0.016 (4)	0.001 (4)
C31	0.033 (3)	0.025 (3)	0.016 (2)	0.003 (2)	0.011 (2)	−0.001 (2)
C32	0.050 (4)	0.022 (3)	0.029 (3)	0.000 (3)	0.019 (3)	−0.004 (2)
C33	0.031 (3)	0.018 (3)	0.012 (2)	0.008 (2)	0.001 (2)	0.0021 (18)
C34	0.023 (3)	0.041 (4)	0.032 (3)	0.001 (3)	0.001 (2)	−0.004 (3)
C35	0.023 (3)	0.015 (3)	0.023 (2)	0.000 (2)	0.001 (2)	0.006 (2)
C36	0.033 (3)	0.020 (3)	0.030 (3)	0.007 (2)	0.007 (2)	−0.003 (2)
C37	0.027 (3)	0.020 (3)	0.031 (3)	−0.004 (2)	0.013 (2)	−0.003 (2)
C38	0.028 (3)	0.029 (4)	0.052 (4)	−0.010 (3)	0.008 (3)	−0.011 (3)

Geometric parameters (Å, º) top

Re1—C03	1.884 (6)	C22—C21	1.37 (2)
Re1—C01	1.895 (5)	C22—C23	1.44 (2)
Re1—C02	1.909 (5)	C22—C221	1.47 (2)
Re1—N1	2.241 (4)	C24—C23	1.35 (3)
Re1—Br2	2.6370 (8)	C24—H24	0.95
Re1—Br1	2.6389 (7)	C23—H23	0.95
N1—C11	1.452 (10)	C21—C26	1.45 (3)
N1—C21	1.47 (2)	C26—H26	0.95
N1—H1A	0.92	C221—H22A	0.98
N1—H1B	0.92	C221—H22B	0.98
N1—H1C	0.92	C221—H22C	0.98
N1—H1D	0.92	C31—C32	1.514 (8)
N2—C31	1.518 (6)	C31—H31A	0.99
N2—C37	1.518 (6)	C31—H31B	0.99
N2—C33	1.518 (6)	C32—H32A	0.98
N2—C35	1.523 (6)	C32—H32B	0.98
O01—C01	1.162 (6)	C32—H32C	0.98
O02—C02	1.145 (6)	C33—C34	1.508 (8)
O03—C03	1.164 (7)	C33—H33A	0.99
C11—C16	1.377 (14)	C33—H33B	0.99
C11—C12	1.385 (12)	C34—H34A	0.98
C12—C13	1.392 (12)	C34—H34B	0.98
C12—C121	1.516 (12)	C34—H34C	0.98
C13—C14	1.372 (13)	C35—C36	1.513 (7)
C13—H13	0.95	C35—H35A	0.99
C14—C15	1.383 (12)	C35—H35B	0.99
C14—H14	0.95	C36—H36A	0.98
C15—C16	1.377 (13)	C36—H36B	0.98
C15—H15	0.95	C36—H36C	0.98
C16—H16	0.95	C37—C38	1.515 (7)
C121—H12A	0.98	C37—H37A	0.99
C121—H12B	0.98	C37—H37B	0.99
C121—H12C	0.98	C38—H38A	0.98
C25—C24	1.36 (3)	C38—H38B	0.98
C25—C26	1.39 (2)	C38—H38C	0.98
C25—H25	0.95

C03—Re1—C01	89.6 (2)	C23—C24—C25	122 (2)
C03—Re1—C02	88.5 (2)	C23—C24—H24	118.9
C01—Re1—C02	89.0 (2)	C25—C24—H24	118.9
C03—Re1—N1	94.1 (2)	C24—C23—C22	121 (2)
C01—Re1—N1	174.31 (19)	C24—C23—H23	119.5
C02—Re1—N1	95.41 (19)	C22—C23—H23	119.5
C03—Re1—Br2	177.68 (17)	C22—C21—C26	120.7 (17)
C01—Re1—Br2	92.67 (16)	C22—C21—N1	120.3 (15)
C02—Re1—Br2	91.17 (16)	C26—C21—N1	119.0 (15)
N1—Re1—Br2	83.64 (11)	C25—C26—C21	118.8 (17)
C03—Re1—Br1	90.87 (16)	C25—C26—H26	120.6
C01—Re1—Br1	93.02 (15)	C21—C26—H26	120.6
C02—Re1—Br1	177.91 (15)	C22—C221—H22A	109.5
N1—Re1—Br1	82.64 (11)	C22—C221—H22B	109.5
Br2—Re1—Br1	89.37 (3)	H22A—C221—H22B	109.5
C11—N1—Re1	118.0 (4)	C22—C221—H22C	109.5
C21—N1—Re1	113.2 (8)	H22A—C221—H22C	109.5
C11—N1—H1A	107.8	H22B—C221—H22C	109.5
C21—N1—H1A	88.4	C32—C31—N2	115.1 (4)
Re1—N1—H1A	107.8	C32—C31—H31A	108.5
C11—N1—H1B	107.8	N2—C31—H31A	108.5
C21—N1—H1B	128.7	C32—C31—H31B	108.5
Re1—N1—H1B	107.8	N2—C31—H31B	108.5
H1A—N1—H1B	107.1	H31A—C31—H31B	107.5
C11—N1—H1C	123.4	C31—C32—H32A	109.5
C21—N1—H1C	108.7	C31—C32—H32B	109.5
Re1—N1—H1C	108.9	H32A—C32—H32B	109.5
H1B—N1—H1C	84.8	C31—C32—H32C	109.5
C11—N1—H1D	86	H32A—C32—H32C	109.5
C21—N1—H1D	109.3	H32B—C32—H32C	109.5
Re1—N1—H1D	108.9	C34—C33—N2	115.2 (4)
H1A—N1—H1D	127.7	C34—C33—H33A	108.5
H1C—N1—H1D	107.7	N2—C33—H33A	108.5
C31—N2—C37	111.6 (4)	C34—C33—H33B	108.5
C31—N2—C33	110.6 (4)	N2—C33—H33B	108.5
C37—N2—C33	107.0 (4)	H33A—C33—H33B	107.5
C31—N2—C35	106.1 (4)	C33—C34—H34A	109.5
C37—N2—C35	110.4 (4)	C33—C34—H34B	109.5
C33—N2—C35	111.2 (4)	H34A—C34—H34B	109.5
O01—C01—Re1	179.1 (5)	C33—C34—H34C	109.5
O02—C02—Re1	176.6 (5)	H34A—C34—H34C	109.5
O03—C03—Re1	178.2 (5)	H34B—C34—H34C	109.5
C16—C11—C12	120.4 (9)	C36—C35—N2	115.4 (4)
C16—C11—N1	118.6 (8)	C36—C35—H35A	108.4
C12—C11—N1	120.9 (8)	N2—C35—H35A	108.4
C11—C12—C13	117.6 (9)	C36—C35—H35B	108.4
C11—C12—C121	121.0 (8)	N2—C35—H35B	108.4
C13—C12—C121	121.3 (8)	H35A—C35—H35B	107.5
C14—C13—C12	122.0 (9)	C35—C36—H36A	109.5
C14—C13—H13	119	C35—C36—H36B	109.5
C12—C13—H13	119	H36A—C36—H36B	109.5
C13—C14—C15	119.8 (9)	C35—C36—H36C	109.5
C13—C14—H14	120.1	H36A—C36—H36C	109.5
C15—C14—H14	120.1	H36B—C36—H36C	109.5
C16—C15—C14	118.8 (8)	C38—C37—N2	115.4 (4)
C16—C15—H15	120.6	C38—C37—H37A	108.4
C14—C15—H15	120.6	N2—C37—H37A	108.4
C11—C16—C15	121.4 (9)	C38—C37—H37B	108.4
C11—C16—H16	119.3	N2—C37—H37B	108.4
C15—C16—H16	119.3	H37A—C37—H37B	107.5
C24—C25—C26	119.9 (17)	C37—C38—H38A	109.5
C24—C25—H25	120.1	C37—C38—H38B	109.5
C26—C25—H25	120.1	H38A—C38—H38B	109.5
C21—C22—C23	117.4 (17)	C37—C38—H38C	109.5
C21—C22—C221	120.7 (16)	H38A—C38—H38C	109.5
C23—C22—C221	121.8 (17)	H38B—C38—H38C	109.5

C03—Re1—N1—C11	−53.5 (5)	C21—C22—C23—C24	2 (3)
C02—Re1—N1—C11	35.4 (5)	C221—C22—C23—C24	179.3 (18)
Br2—Re1—N1—C11	126.0 (5)	C23—C22—C21—C26	−1 (2)
Br1—Re1—N1—C11	−143.8 (5)	C221—C22—C21—C26	−178.4 (16)
C03—Re1—N1—C21	−27.2 (8)	C23—C22—C21—N1	177.8 (14)
C02—Re1—N1—C21	61.6 (8)	C221—C22—C21—N1	1 (2)
Br2—Re1—N1—C21	152.2 (8)	C11—N1—C21—C22	8.0 (12)
Br1—Re1—N1—C21	−117.6 (8)	Re1—N1—C21—C22	−99.0 (15)
C21—N1—C11—C16	−165 (2)	C11—N1—C21—C26	−173 (3)
Re1—N1—C11—C16	−80.3 (8)	Re1—N1—C21—C26	79.9 (15)
C21—N1—C11—C12	11.7 (19)	C24—C25—C26—C21	0 (3)
Re1—N1—C11—C12	96.2 (7)	C22—C21—C26—C25	0 (3)
C16—C11—C12—C13	0.2 (12)	N1—C21—C26—C25	−178.6 (14)
N1—C11—C12—C13	−176.2 (7)	C37—N2—C31—C32	−63.7 (6)
C16—C11—C12—C121	−178.4 (8)	C33—N2—C31—C32	55.3 (6)
N1—C11—C12—C121	5.2 (12)	C35—N2—C31—C32	176.0 (5)
C11—C12—C13—C14	0.4 (12)	C31—N2—C33—C34	56.7 (6)
C121—C12—C13—C14	178.9 (8)	C37—N2—C33—C34	178.4 (5)
C12—C13—C14—C15	−0.7 (13)	C35—N2—C33—C34	−60.9 (6)
C13—C14—C15—C16	0.5 (13)	C31—N2—C35—C36	178.4 (4)
C12—C11—C16—C15	−0.4 (13)	C37—N2—C35—C36	57.3 (6)
N1—C11—C16—C15	176.1 (7)	C33—N2—C35—C36	−61.3 (6)
C14—C15—C16—C11	0.0 (13)	C31—N2—C37—C38	−61.2 (6)
C26—C25—C24—C23	1 (3)	C33—N2—C37—C38	177.7 (5)
C25—C24—C23—C22	−2 (3)	C35—N2—C37—C38	56.6 (6)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1C···Br2ⁱ	0.92	2.7	3.542 (4)	153
N1—H1B···Br1ⁱ	0.92	2.75	3.594 (4)	153
C121—H12C···O03ⁱⁱ	0.98	2.5	3.139 (10)	123
C35—H35B···O03ⁱⁱⁱ	0.99	2.39	3.196 (7)	138
C37—H37A···Br1^iv	0.99	2.92	3.911 (6)	174

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

Experimental details

Crystal data
Chemical formula	(C₈H₂₀N)[ReBr₂(C₇H₉N)(CO)₃]
M_r	667.45
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	10.776 (2), 18.466 (4), 11.745 (2)
β (°)	106.74 (3)
V (Å³)	2238.2 (8)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	9.02
Crystal size (mm)	0.42 × 0.32 × 0.08

Data collection
Diffractometer	Bruker X8 APEXII 4K Kappa CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2004)
T_min, T_max	0.116, 0.532
No. of measured, independent and observed [I > 2σ(I)] reflections	45095, 5371, 4411
R_int	0.072
(sin θ/λ)_max (Å⁻¹)	0.661

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.032, 0.086, 1.06
No. of reflections	5371
No. of parameters	270
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	2.5, −2.99

Computer programs: APEX2 (Bruker, 2005), SAINT-Plus (Bruker, 2004), SAINT-Plus and XPREP (Bruker, 2004), SIR92 (Altomare et al., 1999), SHELXL97 (Sheldrick, 2008), DIAMOND (Brandenburg & Putz, 2004), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1C···Br2ⁱ	0.92	2.7	3.542 (4)	152.8
N1—H1B···Br1ⁱ	0.92	2.75	3.594 (4)	152.7
C121—H12C···O03ⁱⁱ	0.98	2.5	3.139 (10)	123
C35—H35B···O03ⁱⁱⁱ	0.99	2.39	3.196 (7)	138.2
C37—H37A···Br1^iv	0.99	2.92	3.911 (6)	174.1

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

Acknowledgements

Financial assistance from the University of the Free State (UFS), the UFS Advanced Biomolecular Cluster, SASOL and the South African National Research Foundation (SA-NRF/THRIP) is gratefully acknowledged. Part of this material is based on work supported by the SA–NRF/THRIP under grant No. GUN 2068915. Opinions, findings, conclusions or recommendations expressed in this material are those of the authors and do not necessarily reflect the views of the SA–NRF.

References

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