Tetra-ethyl-ammonium tricarbonyl-chlorido(quinoxaline-2-carboxyl-ato-κN,O)rhenate(I).

In the title compound, (C(8)H(20)N)[Re(C(9)H(5)N(2)O(2))Cl(CO)(3)], the Re(I) atom is coordinated facially by three carbonyl groups, the bidentate quinoxaline-2-carbaldehyde ligand and a chloride atom, forming a distorted octahedral geometry.. The crystal packing is controlled by C-H⋯O hydrogen bonding and π-π stacking inter-actions involving the benzene rings, with a centroid-centroid distance of 3.4220 (1) Å.

Related literature

For synthetic background, see: Alberto et al. (1996 ▶). For related structures, see: Schutte et al. (2008 ▶); Wang et al. (2003 ▶); Alvarez et al. (2007 ▶); Brasey et al. (2004 ▶); Mundwiler et al. (2004 ▶); Feng et al. (2007 ▶); Suthiram et al. (2009 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

(C8H20N)[Re(C9H5N2O2)Cl(CO)3]

M = 609.08

Triclinic,

a = 8.402 (5) Å

b = 10.077 (5) Å

c = 13.495 (5) Å

α = 97.433 (5)°

β = 103.141 (5)°

γ = 90.686 (5)°

V = 1102.3 (9) Å3

Z = 2

Mo Kα radiation

μ = 5.67 mm−1

T = 100 K

0.33 × 0.29 × 0.20 mm

Data collection

Bruker X8 APEXII 4K Kappa CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2004 ▶) T min = 0.169, T max = 0.324

22501 measured reflections

5458 independent reflections

4988 reflections with I > 2σ(I)

R int = 0.054

Refinement

R[F 2 > 2σ(F 2)] = 0.027

wR(F 2) = 0.065

S = 1.07

5458 reflections

275 parameters

12 restraints

H-atom parameters constrained

Δρmax = 1.74 e Å−3

Δρmin = −1.04 e Å−3

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: SIR97 (Altomare et al., 1999 ▶); 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/S160053681002893X/pv2307sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053681002893X/pv2307Isup2.hkl

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

(C8H20N)[Re(C9H5N2O2)Cl(CO)3]	Z = 2
Mr = 609.08	F(000) = 596
Triclinic, P1	Dx = 1.835 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71069 Å
a = 8.402 (5) Å	Cell parameters from 9175 reflections
b = 10.077 (5) Å	θ = 2.7–28.3°
c = 13.495 (5) Å	µ = 5.67 mm−1
α = 97.433 (5)°	T = 100 K
β = 103.141 (5)°	Cuboid, red
γ = 90.686 (5)°	0.33 × 0.29 × 0.20 mm
V = 1102.3 (9) Å3

Bruker X8 APEXII 4K Kappa CCD diffractometer	5458 independent reflections
Radiation source: sealed tube	4988 reflections with I > 2σ(I)
graphite	Rint = 0.054
φ & ω scans	θmax = 28.3°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −11→10
Tmin = 0.169, Tmax = 0.324	k = −13→13
22501 measured reflections	l = −17→17

Refinement on F2	12 restraints
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.027	w = 1/[σ2(Fo2) + (0.0211P)2 + 1.8438P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.065	(Δ/σ)max = 0.003
S = 1.07	Δρmax = 1.74 e Å−3
5458 reflections	Δρmin = −1.04 e Å−3
275 parameters

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
Re1	0.528310 (18)	0.255408 (14)	0.783120 (11)	0.01364 (5)
Cl1	0.81842 (12)	0.20551 (10)	0.85067 (7)	0.0205 (2)
O3	0.1770 (4)	0.3314 (3)	0.6974 (2)	0.0304 (7)
C3	0.3080 (5)	0.3001 (4)	0.7268 (3)	0.0208 (8)
N3	0.0788 (4)	0.7963 (3)	0.8126 (2)	0.0139 (6)
O1	0.4040 (4)	0.1531 (3)	0.9570 (2)	0.0279 (7)
O4	0.5167 (3)	0.0596 (3)	0.6987 (2)	0.0182 (6)
N1	0.6229 (4)	0.2820 (3)	0.6466 (2)	0.0124 (6)
O2	0.5953 (4)	0.5310 (3)	0.9133 (2)	0.0290 (7)
C2	0.5683 (5)	0.4271 (4)	0.8632 (3)	0.0191 (8)
C13	−0.0041 (5)	0.8729 (4)	0.8902 (3)	0.0162 (8)
H13A	0.0418	0.8469	0.9572	0.019*
H13B	0.0218	0.9677	0.894	0.019*
C15	0.0262 (5)	0.6478 (4)	0.7929 (3)	0.0198 (8)
H15A	−0.091	0.6396	0.7647	0.024*
H15B	0.0784	0.6037	0.7411	0.024*
C1	0.4532 (5)	0.1938 (4)	0.8923 (3)	0.0195 (8)
C20	0.0905 (5)	0.9922 (4)	0.7091 (3)	0.0236 (9)
H20A	0.0551	1.0511	0.7609	0.035*
H20B	0.0466	1.0193	0.643	0.035*
H20C	0.2078	0.9963	0.7229	0.035*
C14	−0.1876 (5)	0.8518 (4)	0.8673 (3)	0.0214 (8)
H14A	−0.2342	0.8703	0.799	0.032*
H14B	−0.2305	0.911	0.9156	0.032*
H14C	−0.2148	0.7607	0.8729	0.032*
C18	0.3657 (5)	0.7536 (5)	0.7873 (4)	0.0311 (10)
H18A	0.3362	0.66	0.7679	0.047*
H18B	0.4789	0.7645	0.8227	0.047*
H18C	0.3486	0.7974	0.7269	0.047*
C19	0.0298 (5)	0.8491 (4)	0.7098 (3)	0.0160 (8)
H19A	−0.0886	0.8444	0.6882	0.019*
H19B	0.071	0.7903	0.6594	0.019*
C16	0.0657 (6)	0.5747 (4)	0.8857 (4)	0.0296 (10)
H16A	0.1822	0.5716	0.909	0.044*
H16B	0.0185	0.4852	0.8677	0.044*
H16C	0.0215	0.621	0.9395	0.044*
C17	0.2609 (5)	0.8150 (4)	0.8572 (3)	0.0207 (8)
H17A	0.2872	0.7761	0.9207	0.025*
H17B	0.2889	0.9102	0.874	0.025*
O5	0.6377 (4)	−0.0666 (3)	0.5901 (2)	0.0236 (6)
N2	0.7964 (4)	0.2711 (3)	0.4892 (3)	0.0185 (7)
C12	0.6622 (4)	0.3988 (3)	0.6110 (3)	0.0116 (7)
C10	0.6387 (5)	0.6348 (4)	0.6071 (3)	0.0155 (7)
H10	0.5979	0.716	0.629	0.019*
C11	0.6071 (4)	0.5229 (4)	0.6470 (3)	0.0141 (7)
H11	0.5489	0.5285	0.6983	0.017*
C5	0.6598 (5)	0.1677 (4)	0.5993 (3)	0.0143 (7)
C6	0.7465 (5)	0.1632 (4)	0.5210 (3)	0.0184 (8)
H6	0.7696	0.0799	0.4902	0.022*
C7	0.7515 (4)	0.3910 (4)	0.5336 (3)	0.0139 (7)
C4	0.6025 (5)	0.0410 (4)	0.6313 (3)	0.0167 (8)
C8	0.7889 (5)	0.5102 (4)	0.4965 (3)	0.0159 (7)
H8	0.8515	0.5073	0.4477	0.019*
C9	0.7334 (4)	0.6286 (4)	0.5322 (3)	0.0163 (8)
H9	0.7577	0.7064	0.5073	0.02*

	U11	U22	U33	U12	U13	U23
Re1	0.01848 (8)	0.01209 (8)	0.01132 (8)	−0.00015 (5)	0.00457 (6)	0.00329 (5)
Cl1	0.0230 (5)	0.0222 (5)	0.0152 (5)	0.0047 (4)	0.0008 (4)	0.0037 (4)
O3	0.0226 (16)	0.0426 (19)	0.0309 (18)	0.0056 (14)	0.0086 (14)	0.0175 (15)
C3	0.029 (2)	0.024 (2)	0.012 (2)	−0.0069 (17)	0.0097 (17)	0.0064 (16)
N3	0.0119 (15)	0.0165 (15)	0.0126 (16)	0.0013 (12)	0.0022 (12)	0.0002 (12)
O1	0.0362 (18)	0.0315 (17)	0.0191 (16)	−0.0072 (14)	0.0108 (13)	0.0076 (13)
O4	0.0267 (15)	0.0127 (12)	0.0158 (14)	−0.0025 (11)	0.0051 (12)	0.0044 (10)
N1	0.0110 (14)	0.0142 (14)	0.0113 (16)	−0.0001 (11)	0.0009 (12)	0.0025 (12)
O2	0.049 (2)	0.0187 (15)	0.0196 (16)	0.0003 (14)	0.0098 (14)	−0.0005 (12)
C2	0.025 (2)	0.023 (2)	0.0120 (19)	0.0013 (16)	0.0061 (16)	0.0083 (16)
C13	0.0191 (19)	0.0191 (18)	0.0112 (19)	0.0039 (15)	0.0058 (15)	0.0009 (14)
C15	0.022 (2)	0.0164 (18)	0.018 (2)	−0.0023 (15)	0.0019 (16)	−0.0025 (15)
C1	0.021 (2)	0.0199 (19)	0.017 (2)	−0.0021 (15)	0.0020 (16)	0.0022 (15)
C20	0.028 (2)	0.024 (2)	0.021 (2)	0.0015 (17)	0.0094 (18)	0.0061 (17)
C14	0.020 (2)	0.024 (2)	0.023 (2)	0.0041 (16)	0.0096 (17)	0.0043 (17)
C18	0.019 (2)	0.041 (3)	0.032 (3)	0.0088 (19)	0.0047 (19)	0.003 (2)
C19	0.0155 (18)	0.0215 (19)	0.0111 (19)	0.0023 (15)	0.0031 (14)	0.0023 (15)
C16	0.040 (3)	0.019 (2)	0.027 (2)	−0.0015 (18)	0.000 (2)	0.0060 (18)
C17	0.0113 (18)	0.028 (2)	0.019 (2)	−0.0025 (15)	−0.0029 (15)	0.0030 (17)
O5	0.0395 (18)	0.0115 (13)	0.0188 (15)	0.0045 (12)	0.0046 (13)	0.0015 (11)
N2	0.0205 (17)	0.0208 (16)	0.0154 (17)	0.0051 (13)	0.0069 (13)	0.0020 (13)
C12	0.0146 (17)	0.0127 (16)	0.0062 (17)	−0.0021 (13)	−0.0012 (13)	0.0028 (13)
C10	0.0173 (18)	0.0115 (16)	0.0144 (19)	−0.0003 (14)	−0.0027 (15)	0.0011 (14)
C11	0.0140 (17)	0.0175 (17)	0.0093 (18)	0.0012 (14)	−0.0004 (14)	0.0019 (14)
C5	0.0169 (18)	0.0162 (17)	0.0080 (18)	0.0031 (14)	−0.0016 (14)	0.0025 (14)
C6	0.023 (2)	0.0172 (18)	0.015 (2)	0.0064 (15)	0.0056 (16)	0.0002 (15)
C7	0.0134 (17)	0.0166 (17)	0.0106 (18)	0.0023 (14)	0.0003 (14)	0.0026 (14)
C4	0.022 (2)	0.0128 (17)	0.0136 (19)	0.0011 (14)	−0.0012 (15)	0.0040 (14)
C8	0.0151 (18)	0.0208 (18)	0.0115 (19)	−0.0007 (14)	−0.0005 (14)	0.0071 (15)
C9	0.0154 (18)	0.0160 (17)	0.016 (2)	−0.0038 (14)	−0.0023 (15)	0.0059 (14)

Re1—C1	1.899 (4)	C14—H14C	0.96
Re1—C2	1.900 (4)	C18—C17	1.513 (6)
Re1—C3	1.917 (5)	C18—H18A	0.96
Re1—O4	2.136 (3)	C18—H18B	0.96
Re1—N1	2.211 (3)	C18—H18C	0.96
Re1—Cl1	2.4825 (16)	C19—H19A	0.97
O3—C3	1.145 (5)	C19—H19B	0.97
N3—C17	1.511 (5)	C16—H16A	0.96
N3—C19	1.521 (5)	C16—H16B	0.96
N3—C13	1.521 (5)	C16—H16C	0.96
N3—C15	1.527 (5)	C17—H17A	0.97
O1—C1	1.164 (5)	C17—H17B	0.97
O4—C4	1.281 (5)	O5—C4	1.225 (4)
N1—C5	1.319 (5)	N2—C6	1.315 (5)
N1—C12	1.390 (4)	N2—C7	1.374 (5)
O2—C2	1.160 (5)	C12—C11	1.405 (5)
C13—C14	1.508 (5)	C12—C7	1.413 (5)
C13—H13A	0.97	C10—C11	1.360 (5)
C13—H13B	0.97	C10—C9	1.417 (5)
C15—C16	1.510 (6)	C10—H10	0.93
C15—H15A	0.97	C11—H11	0.93
C15—H15B	0.97	C5—C6	1.410 (5)
C20—C19	1.526 (5)	C5—C4	1.506 (5)
C20—H20A	0.96	C6—H6	0.93
C20—H20B	0.96	C7—C8	1.417 (5)
C20—H20C	0.96	C8—C9	1.356 (5)
C14—H14A	0.96	C8—H8	0.93
C14—H14B	0.96	C9—H9	0.93
C1—Re1—C2	88.06 (17)	C17—C18—H18A	109.5
C1—Re1—C3	88.08 (17)	C17—C18—H18B	109.5
C2—Re1—C3	90.12 (17)	H18A—C18—H18B	109.5
C1—Re1—O4	93.58 (14)	C17—C18—H18C	109.5
C2—Re1—O4	172.60 (14)	H18A—C18—H18C	109.5
C3—Re1—O4	97.15 (15)	H18B—C18—H18C	109.5
C1—Re1—N1	167.94 (14)	N3—C19—C20	115.4 (3)
C2—Re1—N1	103.18 (14)	N3—C19—H19A	108.4
C3—Re1—N1	96.14 (14)	C20—C19—H19A	108.4
O4—Re1—N1	74.71 (11)	N3—C19—H19B	108.4
C1—Re1—Cl1	94.68 (13)	C20—C19—H19B	108.4
C2—Re1—Cl1	88.98 (13)	H19A—C19—H19B	107.5
C3—Re1—Cl1	177.06 (11)	C15—C16—H16A	109.5
O4—Re1—Cl1	83.70 (8)	C15—C16—H16B	109.5
N1—Re1—Cl1	81.35 (8)	H16A—C16—H16B	109.5
O3—C3—Re1	176.6 (4)	C15—C16—H16C	109.5
C17—N3—C19	111.5 (3)	H16A—C16—H16C	109.5
C17—N3—C13	106.6 (3)	H16B—C16—H16C	109.5
C19—N3—C13	110.3 (3)	N3—C17—C18	114.5 (3)
C17—N3—C15	110.7 (3)	N3—C17—H17A	108.6
C19—N3—C15	106.6 (3)	C18—C17—H17A	108.6
C13—N3—C15	111.2 (3)	N3—C17—H17B	108.6
C4—O4—Re1	117.4 (2)	C18—C17—H17B	108.6
C5—N1—C12	117.2 (3)	H17A—C17—H17B	107.6
C5—N1—Re1	112.5 (2)	C6—N2—C7	115.9 (3)
C12—N1—Re1	129.9 (2)	N1—C12—C11	120.9 (3)
O2—C2—Re1	178.7 (4)	N1—C12—C7	119.3 (3)
C14—C13—N3	115.2 (3)	C11—C12—C7	119.7 (3)
C14—C13—H13A	108.5	C11—C10—C9	120.4 (3)
N3—C13—H13A	108.5	C11—C10—H10	119.8
C14—C13—H13B	108.5	C9—C10—H10	119.8
N3—C13—H13B	108.5	C10—C11—C12	120.1 (4)
H13A—C13—H13B	107.5	C10—C11—H11	120
C16—C15—N3	115.3 (3)	C12—C11—H11	120
C16—C15—H15A	108.4	N1—C5—C6	121.8 (3)
N3—C15—H15A	108.4	N1—C5—C4	117.0 (3)
C16—C15—H15B	108.4	C6—C5—C4	121.1 (3)
N3—C15—H15B	108.4	N2—C6—C5	123.3 (3)
H15A—C15—H15B	107.5	N2—C6—H6	118.4
O1—C1—Re1	177.9 (4)	C5—C6—H6	118.4
C19—C20—H20A	109.5	N2—C7—C12	122.2 (3)
C19—C20—H20B	109.5	N2—C7—C8	118.7 (3)
H20A—C20—H20B	109.5	C12—C7—C8	119.0 (3)
C19—C20—H20C	109.5	O5—C4—O4	127.0 (4)
H20A—C20—H20C	109.5	O5—C4—C5	118.5 (4)
H20B—C20—H20C	109.5	O4—C4—C5	114.5 (3)
C13—C14—H14A	109.5	C9—C8—C7	120.1 (4)
C13—C14—H14B	109.5	C9—C8—H8	120
H14A—C14—H14B	109.5	C7—C8—H8	120
C13—C14—H14C	109.5	C8—C9—C10	120.6 (3)
H14A—C14—H14C	109.5	C8—C9—H9	119.7
H14B—C14—H14C	109.5	C10—C9—H9	119.7
C1—Re1—O4—C4	−159.2 (3)	C15—N3—C19—C20	−172.6 (3)
C3—Re1—O4—C4	112.3 (3)	C19—N3—C17—C18	−55.5 (4)
Cl1—Re1—O4—C4	−64.9 (3)	C13—N3—C17—C18	−176.0 (3)
C2—Re1—N1—C5	157.7 (3)	C15—N3—C17—C18	63.0 (4)
C3—Re1—N1—C5	−110.7 (3)	C5—N1—C12—C11	171.0 (3)
Cl1—Re1—N1—C5	70.8 (2)	Re1—N1—C12—C7	167.3 (2)
C1—Re1—N1—C12	−174.0 (6)	N1—C12—C11—C10	−176.3 (3)
C3—Re1—N1—C12	76.0 (3)	Re1—N1—C5—C6	−169.4 (3)
O4—Re1—N1—C12	171.8 (3)	C12—N1—C5—C4	−174.2 (3)
Cl1—Re1—N1—C12	−102.4 (3)	Re1—N1—C5—C4	11.5 (4)
C17—N3—C13—C14	−172.0 (3)	C4—C5—C6—N2	178.8 (4)
C19—N3—C13—C14	66.8 (4)	C6—N2—C7—C8	−174.6 (3)
C15—N3—C13—C14	−51.2 (4)	C11—C12—C7—N2	−174.3 (3)
C17—N3—C15—C16	57.8 (5)	N1—C12—C7—C8	179.0 (3)
C19—N3—C15—C16	179.3 (3)	Re1—O4—C4—O5	164.6 (3)
C13—N3—C15—C16	−60.5 (4)	N1—C5—C4—O5	−178.6 (3)
C17—N3—C19—C20	−51.7 (4)	C6—C5—C4—O4	−175.9 (3)
C13—N3—C19—C20	66.6 (4)	N2—C7—C8—C9	174.1 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10···O5i	0.93	2.35	3.046 (5)	131

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C10—H10⋯O5i	0.93	2.35	3.046 (5)	131

Symmetry code: (i) .