Tetra-ethyl-ammonium bromidotricarbon-yl(tropolonato)rhenate(I).

In the title salt, (C(8)H(20)N)[ReBr(C(7)H(5)O(2))(CO)(3)], the Re(I) atom is octa-hedrally surrounded by three facially orientated carbonyl ligands, one bidendate tropolonate ligand and a bromide ligand. The small O-Re-O bite angle of 74.88 (12)° leads to a distortion of the octa-hedral coordination sphere. The bromide ligand and the axial carbonyl ligand are substitutionally disordered over two positions in a 0.922 (3):0.078 (3) ratio. An array of C-H⋯O and C-H⋯Br hydrogen-bonding inter-actions between the cations and neighbouring rhenate anions stabilizes the crystal packing.

Related literature

For the synthesis of the ReI-tricarbonyl synthon, see: Alberto et al. (1996 ▶). A range of related rhenium bidentate complexes have been characterized by Schutte & Visser (2008 ▶); Alberto et al. (1992 ▶, 1996 ▶, 1998 ▶); Abram et al. (1996 ▶); Findeisen & Schmidt (1991 ▶); Egli et al. (1997 ▶), Brasey et al. (2004 ▶); Gibson et al. (1999 ▶); Bochkova et al. (1987 ▶); Cheng et al. (1988 ▶); Mundwiler et al. (2004 ▶). For similar structures, see: Schutte et al. (2007 ▶, 2008 ▶) and for comparable Re—Br distances, see: Schutte et al. (2007 ▶, 2009 ▶).

Experimental

Crystal data

(C8H20N)[ReBr(C7H5O2)(CO)3]

M = 601.5

Monoclinic,

a = 12.334 (5) Å

b = 10.754 (5) Å

c = 16.053 (5) Å

β = 101.983 (5)°

V = 2082.9 (14) Å3

Z = 4

Mo Kα radiation

μ = 7.78 mm−1

T = 100 K

0.58 × 0.18 × 0.17 mm

Data collection

Bruker SMART CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2004 ▶) T min = 0.196, T max = 0.273

16808 measured reflections

5160 independent reflections

4700 reflections with I > 2σ(I)

R int = 0.047

Refinement

R[F 2 > 2σ(F 2)] = 0.034

wR(F 2) = 0.086

S = 1.13

5160 reflections

251 parameters

3 restraints

H-atom parameters constrained

Δρmax = 3.16 e Å−3

Δρmin = −1.41 e Å−3

Data collection: SMART (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 (Brandenburg & Putz, 2005 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810024505/wm2362sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810024505/wm2362Isup2.hkl

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

(C8H20N)[ReBr(C7H5O2)(CO)3]	F(000) = 1160
Mr = 601.5	Dx = 1.918 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 9467 reflections
a = 12.334 (5) Å	θ = 2.3–28.3°
b = 10.754 (5) Å	µ = 7.78 mm−1
c = 16.053 (5) Å	T = 100 K
β = 101.983 (5)°	Cuboid, orange
V = 2082.9 (14) Å3	0.58 × 0.18 × 0.17 mm
Z = 4

Bruker SMART CCD diffractometer	4700 reflections with I > 2σ(I)
graphite	Rint = 0.047
phi and ω scans	θmax = 28.3°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −16→16
Tmin = 0.196, Tmax = 0.273	k = −14→12
16808 measured reflections	l = −21→21
5160 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)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.086	H-atom parameters constrained
S = 1.13	w = 1/[σ2(Fo2) + (0.0337P)2 + 6.0941P] where P = (Fo2 + 2Fc2)/3
5160 reflections	(Δ/σ)max = 0.002
251 parameters	Δρmax = 3.16 e Å−3
3 restraints	Δρmin = −1.41 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	Occ. (<1)
C1	0.8439 (4)	0.5302 (5)	0.5663 (3)	0.0181 (9)
C2	0.9102 (4)	0.7076 (5)	0.4752 (3)	0.0199 (10)
C11	0.5498 (4)	0.5523 (4)	0.3763 (3)	0.0148 (9)
C12	0.5849 (4)	0.6462 (4)	0.3215 (3)	0.0149 (9)
C13	0.5209 (4)	0.6930 (5)	0.2455 (3)	0.0197 (10)
H13	0.5552	0.7546	0.2196	0.024*
C14	0.4145 (4)	0.6621 (6)	0.2027 (3)	0.0274 (12)
H14	0.3896	0.7047	0.152	0.033*
C15	0.3397 (4)	0.5777 (6)	0.2239 (3)	0.0310 (13)
H15	0.2724	0.5697	0.1854	0.037*
C16	0.3543 (4)	0.5036 (6)	0.2965 (3)	0.0247 (11)
H16	0.2949	0.4524	0.3006	0.03*
C17	0.4455 (4)	0.4958 (5)	0.3636 (3)	0.0205 (10)
H17	0.4355	0.444	0.4077	0.025*
C21	0.5919 (4)	0.0054 (5)	0.3394 (3)	0.0208 (10)
H21A	0.6032	−0.0001	0.2814	0.025*
H21B	0.6263	−0.0671	0.3698	0.025*
C22	0.4687 (4)	0.0006 (6)	0.3370 (3)	0.0253 (11)
H22A	0.4331	0.0706	0.3056	0.038*
H22B	0.4563	0.003	0.394	0.038*
H22C	0.4385	−0.075	0.3098	0.038*
C23	0.7703 (4)	0.1180 (5)	0.3677 (3)	0.0212 (10)
H23A	0.7689	0.1153	0.3071	0.025*
H23B	0.8066	0.1947	0.3898	0.025*
C24	0.8381 (5)	0.0097 (6)	0.4099 (4)	0.0290 (12)
H24A	0.8041	−0.0668	0.3872	0.044*
H24B	0.8416	0.0125	0.4702	0.044*
H24C	0.9117	0.0146	0.3991	0.044*
C25	0.6461 (4)	0.1209 (5)	0.4744 (3)	0.0208 (10)
H25A	0.673	0.0413	0.4987	0.025*
H25B	0.5693	0.1285	0.479	0.025*
C26	0.7123 (5)	0.2234 (6)	0.5273 (3)	0.0303 (12)
H26A	0.789	0.2158	0.5247	0.045*
H26B	0.7045	0.2161	0.5854	0.045*
H26C	0.685	0.303	0.5052	0.045*
C27	0.5946 (4)	0.2388 (5)	0.3406 (3)	0.0218 (10)
H27A	0.5218	0.2442	0.3544	0.026*
H27B	0.6373	0.3097	0.3664	0.026*
C28	0.5810 (5)	0.2483 (5)	0.2445 (3)	0.0261 (11)
H28A	0.5453	0.3254	0.2251	0.039*
H28B	0.5366	0.1802	0.2178	0.039*
H28C	0.6525	0.2452	0.2298	0.039*
N1	0.6509 (3)	0.1205 (4)	0.3806 (3)	0.0175 (8)
O1	0.8829 (3)	0.4790 (4)	0.6285 (2)	0.0295 (9)
O2	0.9905 (3)	0.7658 (4)	0.4826 (2)	0.0278 (8)
O11	0.6230 (3)	0.5185 (3)	0.44163 (19)	0.0156 (6)
O12	0.6850 (3)	0.6885 (3)	0.34718 (19)	0.0158 (6)
Re1	0.778478 (14)	0.611175 (17)	0.462429 (10)	0.01392 (7)
Br1A	0.66965 (4)	0.77746 (5)	0.53345 (3)	0.01591 (18)	0.922 (3)
C3A	0.8454 (5)	0.4916 (7)	0.4061 (4)	0.0190 (12)	0.922 (3)
O3A	0.8876 (5)	0.4139 (5)	0.3694 (3)	0.0257 (10)	0.922 (3)
Br1B	0.8340 (11)	0.4525 (12)	0.3685 (8)	0.043 (3)	0.078 (3)
C3B	0.718 (5)	0.741 (4)	0.522 (3)	0.0190 (12)	0.078 (3)
O3B	0.679 (5)	0.816 (4)	0.554 (4)	0.0257 (10)	0.078 (3)

	U11	U22	U33	U12	U13	U23
C1	0.019 (2)	0.020 (3)	0.017 (2)	0.0019 (18)	0.0063 (16)	0.0018 (17)
C2	0.022 (2)	0.022 (3)	0.015 (2)	0.002 (2)	0.0019 (17)	0.0011 (17)
C11	0.019 (2)	0.015 (2)	0.0106 (18)	0.0009 (18)	0.0040 (15)	−0.0007 (16)
C12	0.019 (2)	0.012 (2)	0.0143 (19)	0.0004 (18)	0.0061 (16)	−0.0004 (16)
C13	0.020 (2)	0.025 (3)	0.015 (2)	−0.0010 (19)	0.0069 (17)	0.0039 (17)
C14	0.021 (3)	0.040 (3)	0.019 (2)	0.000 (2)	0.0005 (18)	0.013 (2)
C15	0.014 (2)	0.050 (4)	0.026 (3)	−0.003 (2)	−0.0043 (19)	0.013 (2)
C16	0.016 (2)	0.035 (3)	0.023 (2)	−0.003 (2)	0.0035 (18)	0.004 (2)
C17	0.021 (2)	0.025 (3)	0.017 (2)	−0.002 (2)	0.0064 (17)	0.0021 (19)
C21	0.027 (2)	0.016 (2)	0.021 (2)	−0.001 (2)	0.0083 (18)	−0.0033 (18)
C22	0.024 (3)	0.029 (3)	0.024 (2)	−0.003 (2)	0.0067 (19)	−0.005 (2)
C23	0.019 (2)	0.019 (3)	0.029 (2)	0.0013 (19)	0.0124 (19)	0.0008 (19)
C24	0.026 (3)	0.027 (3)	0.034 (3)	0.005 (2)	0.006 (2)	0.002 (2)
C25	0.024 (3)	0.022 (3)	0.018 (2)	0.000 (2)	0.0079 (18)	0.0031 (18)
C26	0.044 (3)	0.024 (3)	0.021 (2)	−0.005 (2)	0.004 (2)	−0.001 (2)
C27	0.029 (3)	0.018 (3)	0.020 (2)	0.004 (2)	0.0085 (18)	0.0035 (18)
C28	0.032 (3)	0.026 (3)	0.022 (2)	0.005 (2)	0.009 (2)	0.005 (2)
N1	0.020 (2)	0.014 (2)	0.0201 (19)	0.0030 (16)	0.0089 (15)	0.0022 (15)
O1	0.0248 (19)	0.042 (3)	0.0206 (17)	0.0058 (17)	0.0027 (14)	0.0102 (16)
O2	0.0224 (19)	0.029 (2)	0.0307 (19)	−0.0054 (16)	0.0031 (14)	0.0015 (16)
O11	0.0141 (15)	0.0185 (18)	0.0134 (14)	−0.0016 (13)	0.0009 (11)	0.0031 (12)
O12	0.0149 (15)	0.0179 (18)	0.0149 (14)	−0.0020 (13)	0.0036 (11)	0.0022 (12)
Re1	0.01479 (11)	0.01596 (11)	0.01091 (9)	−0.00006 (7)	0.00243 (6)	0.00038 (6)
Br1A	0.0174 (3)	0.0161 (3)	0.0149 (3)	0.0001 (2)	0.00479 (18)	−0.00174 (17)
C3A	0.022 (3)	0.021 (3)	0.015 (3)	−0.006 (2)	0.004 (2)	−0.005 (2)
O3A	0.025 (3)	0.025 (3)	0.029 (2)	0.008 (2)	0.012 (2)	−0.0041 (18)
Br1B	0.048 (7)	0.039 (7)	0.045 (6)	−0.014 (5)	0.017 (6)	0.010 (5)
C3B	0.022 (3)	0.021 (3)	0.015 (3)	−0.006 (2)	0.004 (2)	−0.005 (2)
O3B	0.025 (3)	0.025 (3)	0.029 (2)	0.008 (2)	0.012 (2)	−0.0041 (18)

C1—O1	1.153 (6)	C23—H23A	0.97
C1—Re1	1.906 (5)	C23—H23B	0.97
C2—O2	1.156 (6)	C24—H24A	0.96
C2—Re1	1.903 (5)	C24—H24B	0.96
C11—O11	1.286 (5)	C24—H24C	0.96
C11—C17	1.398 (7)	C25—N1	1.520 (6)
C11—C12	1.462 (6)	C25—C26	1.521 (7)
C12—O12	1.300 (5)	C25—H25A	0.97
C12—C13	1.402 (6)	C25—H25B	0.97
C13—C14	1.389 (7)	C26—H26A	0.96
C13—H13	0.93	C26—H26B	0.96
C14—C15	1.385 (8)	C26—H26C	0.96
C14—H14	0.93	C27—C28	1.520 (6)
C15—C16	1.392 (7)	C27—N1	1.525 (6)
C15—H15	0.93	C27—H27A	0.97
C16—C17	1.390 (7)	C27—H27B	0.97
C16—H16	0.93	C28—H28A	0.96
C17—H17	0.93	C28—H28B	0.96
C21—C22	1.513 (7)	C28—H28C	0.96
C21—N1	1.517 (6)	O11—Re1	2.126 (3)
C21—H21A	0.97	O12—Re1	2.135 (3)
C21—H21B	0.97	Re1—C3A	1.861 (7)
C22—H22A	0.96	Re1—C3B	1.923 (18)
C22—H22B	0.96	Re1—Br1B	2.467 (16)
C22—H22C	0.96	Re1—Br1A	2.6334 (9)
C23—C24	1.510 (7)	C3A—O3A	1.201 (9)
C23—N1	1.529 (6)	C3B—O3B	1.123 (18)
O1—C1—Re1	178.7 (5)	H26A—C26—H26B	109.5
O2—C2—Re1	179.5 (5)	C25—C26—H26C	109.5
O11—C11—C17	117.7 (4)	H26A—C26—H26C	109.5
O11—C11—C12	116.1 (4)	H26B—C26—H26C	109.5
C17—C11—C12	126.2 (4)	C28—C27—N1	115.3 (4)
O12—C12—C13	118.4 (4)	C28—C27—H27A	108.4
O12—C12—C11	115.6 (4)	N1—C27—H27A	108.4
C13—C12—C11	126.0 (4)	C28—C27—H27B	108.4
C14—C13—C12	130.4 (5)	N1—C27—H27B	108.4
C14—C13—H13	114.8	H27A—C27—H27B	107.5
C12—C13—H13	114.8	C27—C28—H28A	109.5
C15—C14—C13	130.1 (5)	C27—C28—H28B	109.5
C15—C14—H14	114.9	H28A—C28—H28B	109.5
C13—C14—H14	114.9	C27—C28—H28C	109.5
C14—C15—C16	127.1 (5)	H28A—C28—H28C	109.5
C14—C15—H15	116.5	H28B—C28—H28C	109.5
C16—C15—H15	116.5	C21—N1—C25	108.7 (4)
C17—C16—C15	128.8 (5)	C21—N1—C27	111.2 (4)
C17—C16—H16	115.6	C25—N1—C27	107.9 (4)
C15—C16—H16	115.6	C21—N1—C23	108.3 (4)
C16—C17—C11	131.3 (5)	C25—N1—C23	111.8 (4)
C16—C17—H17	114.4	C27—N1—C23	109.0 (4)
C11—C17—H17	114.4	C11—O11—Re1	116.9 (3)
C22—C21—N1	115.3 (4)	C12—O12—Re1	116.4 (3)
C22—C21—H21A	108.4	C3A—Re1—C2	88.5 (2)
N1—C21—H21A	108.4	C3A—Re1—C1	87.7 (2)
C22—C21—H21B	108.4	C2—Re1—C1	87.6 (2)
N1—C21—H21B	108.4	C3A—Re1—C3B	176 (2)
H21A—C21—H21B	107.5	C2—Re1—C3B	88 (2)
C21—C22—H22A	109.5	C1—Re1—C3B	92.1 (19)
C21—C22—H22B	109.5	C3A—Re1—O11	94.4 (2)
H22A—C22—H22B	109.5	C2—Re1—O11	174.40 (17)
C21—C22—H22C	109.5	C1—Re1—O11	97.33 (17)
H22A—C22—H22C	109.5	C3B—Re1—O11	89 (2)
H22B—C22—H22C	109.5	C3A—Re1—O12	93.6 (2)
C24—C23—N1	114.4 (4)	C2—Re1—O12	100.19 (16)
C24—C23—H23A	108.7	C1—Re1—O12	172.18 (16)
N1—C23—H23A	108.7	C3B—Re1—O12	87.1 (18)
C24—C23—H23B	108.7	O11—Re1—O12	74.88 (12)
N1—C23—H23B	108.7	C3A—Re1—Br1B	10.7 (4)
H23A—C23—H23B	107.6	C2—Re1—Br1B	96.0 (3)
C23—C24—H24A	109.5	C1—Re1—Br1B	95.6 (3)
C23—C24—H24B	109.5	C3B—Re1—Br1B	171.5 (19)
H24A—C24—H24B	109.5	O11—Re1—Br1B	86.3 (3)
C23—C24—H24C	109.5	O12—Re1—Br1B	84.8 (3)
H24A—C24—H24C	109.5	C3A—Re1—Br1A	175.61 (19)
H24B—C24—H24C	109.5	C2—Re1—Br1A	94.80 (15)
N1—C25—C26	115.4 (4)	C1—Re1—Br1A	95.34 (14)
N1—C25—H25A	108.4	C3B—Re1—Br1A	7.5 (19)
C26—C25—H25A	108.4	O11—Re1—Br1A	82.07 (9)
N1—C25—H25B	108.4	O12—Re1—Br1A	83.01 (9)
C26—C25—H25B	108.4	Br1B—Re1—Br1A	165.0 (3)
H25A—C25—H25B	107.5	O3A—C3A—Re1	179.3 (6)
C25—C26—H26A	109.5	O3B—C3B—Re1	177 (6)
C25—C26—H26B	109.5

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13···O3Ai	0.93	2.43	3.344 (7)	169
C25—H25A···Br1Aii	0.97	2.89	3.809 (5)	158
C26—H26C···O11	0.96	2.58	3.542 (7)	176
C27—H27B···O11	0.97	2.57	3.401 (6)	143

Table 1

Selected bond lengths (Å)

C1—Re1	1.906 (5)
C2—Re1	1.903 (5)
O11—Re1	2.126 (3)
O12—Re1	2.135 (3)
Re1—C3A	1.861 (7)
Re1—C3B	1.923 (18)
Re1—Br1B	2.467 (16)
Re1—Br1A	2.6334 (9)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C13—H13⋯O3Ai	0.93	2.43	3.344 (7)	169
C25—H25A⋯Br1Aii	0.97	2.89	3.809 (5)	158
C26—H26C⋯O11	0.96	2.58	3.542 (7)	176
C27—H27B⋯O11	0.97	2.57	3.401 (6)	143

Symmetry codes: (i) ; (ii) .