Tetra-ethyl-ammonium (acetyl-acetonato)bromidotricarbonyl-rhenate(I).

In the title compound, (C(8)H(20)N)[ReBr(C(5)H(7)O(2))(CO)(3)], the Re(I) atom in the rhenate anion is surrounded by three carbonyl ligands orientated in a facial arrangement, a bromide ligand and an acetyl-acetonate ligand, leading to a distorted octa-hedral ReC(3)BrO(2) coordination with a O-Re-O bite angle of 85.66 (7)°. An array of C-H⋯O and C-H⋯Br hydrogen-bonding inter-actions 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 ▶). For related rhenium–tricarbonyl complexes, see: Mundwiler et al. (2004 ▶); Wang et al. (2003 ▶); Saw et al. (2006 ▶). For studies of related rhenium(V) compounds, see: Roodt et al. (1992 ▶); Purcell et al. (1989 ▶). For acetyl­acetonato complexes and related structures, see: Brink et al. (2007a ▶,b ▶; 2010 ▶); Steyl & Hill (2009 ▶); Herbst et al. (2010 ▶). For a rhenium complex with pyridine and acetyl­acetonato ligands, see: Benny et al. (2008 ▶). For related structures, see: Schutte et al. (2009 ▶, 2010 ▶).

Experimental

Crystal data

(C8H20N)[ReBr(C5H7O2)(CO)3]

M = 579.5

Orthorhombic,

a = 13.0931 (1) Å

b = 14.5865 (1) Å

c = 20.8724 (2) Å

V = 3986.26 (6) Å3

Z = 8

Mo Kα radiation

μ = 8.12 mm−1

T = 100 K

0.26 × 0.13 × 0.08 mm

Data collection

Oxford Diffraction Xcalibur3 CCD diffractometer

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2006 ▶) T min = 0.227, T max = 0.563

30330 measured reflections

4819 independent reflections

3641 reflections with I > 2σ(I)

R int = 0.031

Refinement

R[F 2 > 2σ(F 2)] = 0.019

wR(F 2) = 0.047

S = 1.02

4819 reflections

223 parameters

H-atom parameters constrained

Δρmax = 1.35 e Å−3

Δρmin = −0.71 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2006 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2006 ▶); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); 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 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810050105/wm2432sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810050105/wm2432Isup2.hkl

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

(C8H20N)[ReBr(C5H7O2)(CO)3]	F(000) = 2240
Mr = 579.5	Dx = 1.931 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 16272 reflections
a = 13.0931 (1) Å	θ = 2.3–33.0°
b = 14.5865 (1) Å	µ = 8.12 mm−1
c = 20.8724 (2) Å	T = 100 K
V = 3986.26 (6) Å3	Parallelepiped, colourless
Z = 8	0.26 × 0.13 × 0.08 mm

Oxford Diffraction Xcalibur3 CCD diffractometer	4819 independent reflections
Radiation source: Enhance (Mo) X-ray Source	3641 reflections with I > 2σ(I)
graphite	Rint = 0.031
Detector resolution: 16.1829 pixels mm-1	θmax = 28°, θmin = 2.3°
ω–scans	h = −17→16
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2006)	k = −19→15
Tmin = 0.227, Tmax = 0.563	l = −27→27
30330 measured reflections

Refinement on F2	0 restraints
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.019	w = 1/[σ2(Fo2) + (0.0251P)2] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.047	(Δ/σ)max = 0.002
S = 1.02	Δρmax = 1.35 e Å−3
4819 reflections	Δρmin = −0.71 e Å−3
223 parameters

Experimental. The intensity data was collected on a Oxford Diffraction Xcalibur 3 area detector diffractometer using an exposure time of 10 s/frame. A total of 552 frames were collected with a frame width of 0.75° covering up to θ = 28.00° with 100.0% 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.

	x	y	z	Uiso*/Ueq
C1	0.6479 (2)	0.59694 (18)	0.79693 (14)	0.0171 (6)
C02	0.4190 (2)	0.79609 (18)	0.82159 (14)	0.0178 (6)
C01	0.5566 (2)	0.91066 (19)	0.86140 (14)	0.0170 (6)
C2	0.7475 (2)	0.62159 (19)	0.81179 (14)	0.0198 (6)
H2	0.7987	0.5764	0.8052	0.024*
C3	0.7799 (2)	0.70650 (19)	0.83555 (14)	0.0186 (6)
C03	0.5822 (2)	0.82991 (18)	0.74731 (16)	0.0174 (6)
C4	0.8919 (2)	0.7204 (2)	0.84831 (16)	0.0253 (7)
H4A	0.9119	0.7822	0.8349	0.038*
H4B	0.9315	0.675	0.8242	0.038*
H4C	0.9054	0.713	0.8942	0.038*
C5	0.6255 (2)	0.50244 (18)	0.77154 (16)	0.0231 (7)
H5A	0.5809	0.4699	0.8016	0.035*
H5B	0.6896	0.4685	0.7666	0.035*
H5C	0.5915	0.5074	0.7299	0.035*
C31	0.3312 (2)	0.9931 (2)	0.97904 (15)	0.0247 (7)
H31A	0.3463	1.0204	1.0214	0.03*
H31B	0.391	1.0043	0.9511	0.03*
C32	0.3183 (3)	0.88969 (19)	0.98731 (17)	0.0318 (8)
H32A	0.2625	0.8776	1.0175	0.048*
H32B	0.3818	0.8633	1.004	0.048*
H32C	0.3022	0.8618	0.9458	0.048*
C33	0.2623 (2)	1.14451 (18)	0.94940 (15)	0.0214 (6)
H33A	0.1989	1.1775	0.9377	0.026*
H33B	0.2816	1.1642	0.9931	0.026*
C34	0.3465 (2)	1.1732 (2)	0.90338 (17)	0.0304 (8)
H34A	0.4098	1.141	0.9144	0.046*
H34B	0.3574	1.2395	0.9066	0.046*
H34C	0.3265	1.1576	0.8595	0.046*
C35	0.2202 (2)	1.00610 (19)	0.88378 (14)	0.0191 (6)
H35A	0.2853	1.0071	0.8597	0.023*
H35B	0.1979	0.9414	0.887	0.023*
C36	0.1410 (3)	1.0589 (2)	0.84595 (15)	0.0273 (7)
H36A	0.0767	1.0606	0.87	0.041*
H36B	0.1297	1.0286	0.8046	0.041*
H36C	0.1652	1.1216	0.8387	0.041*
C37	0.1443 (2)	1.02603 (19)	0.99096 (14)	0.0190 (6)
H37A	0.0881	1.0637	0.9733	0.023*
H37B	0.1242	0.9609	0.9868	0.023*
C38	0.1560 (3)	1.0482 (2)	1.06086 (15)	0.0302 (8)
H38A	0.2073	1.0075	1.0799	0.045*
H38B	0.0904	1.0394	1.0826	0.045*
H38C	0.1779	1.1121	1.0656	0.045*
N1	0.23955 (16)	1.04213 (14)	0.95068 (11)	0.0148 (5)
O1	0.56968 (13)	0.64852 (12)	0.80201 (11)	0.0186 (4)
O02	0.33086 (15)	0.80287 (13)	0.81550 (11)	0.0234 (5)
O2	0.72326 (14)	0.77461 (13)	0.84811 (10)	0.0201 (5)
O01	0.54896 (15)	0.98593 (13)	0.87843 (11)	0.0240 (5)
O03	0.59154 (15)	0.85547 (14)	0.69515 (11)	0.0240 (5)
Re1	0.563458 (8)	0.787480 (7)	0.832299 (6)	0.01437 (4)
Br1	0.54691 (2)	0.718131 (18)	0.948917 (14)	0.01961 (7)

	U11	U22	U33	U12	U13	U23
C1	0.0202 (15)	0.0158 (14)	0.0154 (16)	−0.0001 (11)	0.0013 (12)	0.0039 (11)
C02	0.0237 (16)	0.0141 (14)	0.0155 (16)	−0.0029 (11)	0.0002 (12)	0.0010 (11)
C01	0.0139 (14)	0.0209 (15)	0.0162 (15)	−0.0023 (12)	−0.0018 (12)	0.0059 (12)
C2	0.0169 (14)	0.0190 (14)	0.0235 (17)	0.0062 (12)	0.0028 (13)	0.0006 (12)
C3	0.0140 (13)	0.0214 (15)	0.0206 (16)	−0.0013 (11)	0.0009 (12)	0.0064 (13)
C03	0.0118 (14)	0.0137 (13)	0.0267 (18)	0.0000 (11)	−0.0001 (12)	−0.0026 (13)
C4	0.0136 (14)	0.0275 (17)	0.035 (2)	0.0016 (13)	−0.0001 (13)	0.0016 (14)
C5	0.0241 (16)	0.0174 (15)	0.0277 (18)	0.0004 (12)	0.0030 (13)	−0.0031 (13)
C31	0.0179 (15)	0.0329 (17)	0.0233 (18)	0.0056 (13)	−0.0029 (13)	0.0012 (13)
C32	0.0355 (19)	0.0301 (17)	0.0298 (19)	0.0142 (15)	−0.0017 (16)	0.0071 (14)
C33	0.0214 (15)	0.0176 (14)	0.0253 (18)	−0.0068 (12)	0.0006 (13)	−0.0039 (13)
C34	0.0313 (19)	0.0287 (17)	0.031 (2)	−0.0122 (14)	0.0023 (15)	0.0035 (14)
C35	0.0246 (15)	0.0176 (14)	0.0152 (16)	0.0018 (12)	−0.0013 (13)	−0.0023 (12)
C36	0.0371 (19)	0.0215 (16)	0.0233 (19)	−0.0005 (14)	−0.0082 (14)	0.0029 (13)
C37	0.0164 (14)	0.0196 (14)	0.0210 (16)	−0.0005 (11)	0.0043 (12)	0.0015 (12)
C38	0.0336 (19)	0.0355 (19)	0.0213 (19)	0.0006 (15)	0.0078 (14)	0.0000 (14)
N1	0.0144 (12)	0.0151 (11)	0.0148 (13)	−0.0007 (9)	−0.0016 (10)	0.0001 (10)
O1	0.0115 (10)	0.0127 (9)	0.0317 (12)	−0.0014 (8)	−0.0013 (9)	−0.0057 (9)
O02	0.0139 (11)	0.0205 (11)	0.0360 (14)	0.0040 (8)	−0.0083 (9)	−0.0017 (9)
O2	0.0102 (9)	0.0186 (10)	0.0316 (13)	−0.0001 (8)	−0.0021 (8)	−0.0019 (9)
O01	0.0265 (12)	0.0162 (10)	0.0294 (13)	−0.0013 (9)	−0.0042 (10)	−0.0018 (9)
O03	0.0256 (11)	0.0230 (11)	0.0236 (12)	−0.0028 (9)	0.0054 (10)	−0.0003 (10)
Re1	0.01154 (6)	0.01270 (6)	0.01887 (7)	−0.00035 (4)	−0.00109 (4)	−0.00012 (5)
Br1	0.02132 (15)	0.01855 (13)	0.01895 (16)	−0.00067 (12)	−0.00405 (11)	0.00209 (12)

C1—O1	1.275 (3)	C32—H32C	0.98
C1—C2	1.388 (4)	C33—C34	1.521 (4)
C1—C5	1.505 (4)	C33—N1	1.523 (3)
C02—O02	1.165 (3)	C33—H33A	0.99
C02—Re1	1.909 (3)	C33—H33B	0.99
C01—O01	1.158 (3)	C34—H34A	0.98
C01—O01	1.158 (3)	C34—H34B	0.98
C01—Re1	1.899 (3)	C34—H34C	0.98
C2—C3	1.400 (4)	C35—C36	1.513 (4)
C2—H2	0.95	C35—N1	1.513 (4)
C3—O2	1.267 (3)	C35—H35A	0.99
C3—C4	1.504 (4)	C35—H35B	0.99
C03—O03	1.157 (4)	C36—H36A	0.98
C03—Re1	1.895 (3)	C36—H36B	0.98
C4—H4A	0.98	C36—H36C	0.98
C4—H4B	0.98	C37—C38	1.502 (4)
C4—H4C	0.98	C37—N1	1.522 (3)
C5—H5A	0.98	C37—H37A	0.99
C5—H5B	0.98	C37—H37B	0.99
C5—H5C	0.98	C38—H38A	0.98
C31—N1	1.517 (3)	C38—H38B	0.98
C31—C32	1.528 (4)	C38—H38C	0.98
C31—H31A	0.99	O1—Re1	2.1248 (18)
C31—H31B	0.99	O2—Re1	2.1265 (19)
C32—H32A	0.98	Re1—Br1	2.6448 (3)
C32—H32B	0.98
O1—C1—C2	125.7 (3)	H34B—C34—H34C	109.5
O1—C1—C5	114.4 (2)	C36—C35—N1	114.8 (2)
C2—C1—C5	119.9 (3)	C36—C35—H35A	108.6
O02—C02—Re1	178.8 (2)	N1—C35—H35A	108.6
O01—C01—Re1	177.7 (2)	C36—C35—H35B	108.6
O01—C01—Re1	177.7 (2)	N1—C35—H35B	108.6
C1—C2—C3	126.4 (3)	H35A—C35—H35B	107.5
C1—C2—H2	116.8	C35—C36—H36A	109.5
C3—C2—H2	116.8	C35—C36—H36B	109.5
O2—C3—C2	126.1 (3)	H36A—C36—H36B	109.5
O2—C3—C4	115.4 (2)	C35—C36—H36C	109.5
C2—C3—C4	118.5 (3)	H36A—C36—H36C	109.5
O03—C03—Re1	178.6 (3)	H36B—C36—H36C	109.5
C3—C4—H4A	109.5	C38—C37—N1	114.8 (2)
C3—C4—H4B	109.5	C38—C37—H37A	108.6
H4A—C4—H4B	109.5	N1—C37—H37A	108.6
C3—C4—H4C	109.5	C38—C37—H37B	108.6
H4A—C4—H4C	109.5	N1—C37—H37B	108.6
H4B—C4—H4C	109.5	H37A—C37—H37B	107.5
C1—C5—H5A	109.5	C37—C38—H38A	109.5
C1—C5—H5B	109.5	C37—C38—H38B	109.5
H5A—C5—H5B	109.5	H38A—C38—H38B	109.5
C1—C5—H5C	109.5	C37—C38—H38C	109.5
H5A—C5—H5C	109.5	H38A—C38—H38C	109.5
H5B—C5—H5C	109.5	H38B—C38—H38C	109.5
N1—C31—C32	115.0 (2)	C35—N1—C31	109.2 (2)
N1—C31—H31A	108.5	C35—N1—C37	108.6 (2)
C32—C31—H31A	108.5	C31—N1—C37	111.1 (2)
N1—C31—H31B	108.5	C35—N1—C33	110.9 (2)
C32—C31—H31B	108.5	C31—N1—C33	108.3 (2)
H31A—C31—H31B	107.5	C37—N1—C33	108.7 (2)
C31—C32—H32A	109.5	C1—O1—Re1	128.19 (17)
C31—C32—H32B	109.5	C3—O2—Re1	127.81 (18)
H32A—C32—H32B	109.5	C03—Re1—C01	89.80 (12)
C31—C32—H32C	109.5	C03—Re1—C02	89.85 (12)
H32A—C32—H32C	109.5	C01—Re1—C02	85.88 (11)
H32B—C32—H32C	109.5	C03—Re1—O1	91.61 (10)
C34—C33—N1	115.0 (2)	C01—Re1—O1	178.54 (10)
C34—C33—H33A	108.5	C02—Re1—O1	93.78 (9)
N1—C33—H33A	108.5	C03—Re1—O2	92.67 (10)
C34—C33—H33B	108.5	C01—Re1—O2	94.63 (9)
N1—C33—H33B	108.5	C02—Re1—O2	177.43 (10)
H33A—C33—H33B	107.5	O1—Re1—O2	85.66 (7)
C33—C34—H34A	109.5	C03—Re1—Br1	175.69 (8)
C33—C34—H34B	109.5	C01—Re1—Br1	93.65 (9)
H34A—C34—H34B	109.5	C02—Re1—Br1	92.97 (9)
C33—C34—H34C	109.5	O1—Re1—Br1	84.96 (6)
H34A—C34—H34C	109.5	O2—Re1—Br1	84.49 (6)
O1—C1—C2—C3	0.8 (5)	C34—C33—N1—C31	67.4 (3)
C5—C1—C2—C3	179.9 (3)	C34—C33—N1—C37	−171.7 (2)
C1—C2—C3—O2	0.9 (5)	C2—C1—O1—Re1	1.3 (4)
C1—C2—C3—C4	−179.5 (3)	C5—C1—O1—Re1	−177.82 (19)
C36—C35—N1—C31	−171.2 (2)	C2—C3—O2—Re1	−4.3 (4)
C36—C35—N1—C37	67.6 (3)	C4—C3—O2—Re1	176.09 (19)
C36—C35—N1—C33	−51.8 (3)	C1—O1—Re1—C03	89.5 (3)
C32—C31—N1—C35	−62.4 (3)	C1—O1—Re1—C02	179.5 (2)
C32—C31—N1—C37	57.3 (3)	C1—O1—Re1—O2	−3.0 (2)
C32—C31—N1—C33	176.6 (2)	C1—O1—Re1—Br1	−87.9 (2)
C38—C37—N1—C35	173.2 (2)	C3—O2—Re1—C03	−86.9 (2)
C38—C37—N1—C31	53.1 (3)	C3—O2—Re1—C01	−177.0 (2)
C38—C37—N1—C33	−66.1 (3)	C3—O2—Re1—O1	4.5 (2)
C34—C33—N1—C35	−52.4 (3)	C3—O2—Re1—Br1	89.8 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C31—H31A···O01i	0.99	2.5	3.378 (4)	147.
C31—H31B···O01	0.99	2.58	3.543 (4)	165.
C35—H35B···O03ii	0.99	2.54	3.221 (3)	126.
C36—H36B···O03ii	0.98	2.57	3.155 (4)	118
C37—H37A···Br1iii	0.99	2.91	3.859 (3)	161.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C31—H31A⋯O01i	0.99	2.5	3.378 (4)	147
C31—H31B⋯O01	0.99	2.58	3.543 (4)	165
C35—H35B⋯O03ii	0.99	2.54	3.221 (3)	126
C36—H36B⋯O03ii	0.98	2.57	3.155 (4)	118
C37—H37A⋯Br1iii	0.99	2.91	3.859 (3)	161

Symmetry codes: (i) ; (ii) ; (iii) .