Tetra­ethyl­ammonium tricarbonyl­chlorido(quinoxaline-2-carboxyl­ato-κ2N1,O)rhenate(I)

Suthiram, J.; Zeevaart, J.R.; Visser, H.G.; Roodt, A.

doi:10.1107/S160053681002893X

metal-organic compounds

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ISSN: 2056-9890

Volume 66| Part 8| August 2010| Pages m1042-m1043

https://doi.org/10.1107/S160053681002893X

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Tetraethylammonium tricarbonylchlorido(quinoxaline-2-carboxylato-κ²N¹,O)rhenate(I)

Janine Suthiram,^a Jan Rijn Zeevaart,^b Hendrik G. Visser ^c ^* and Andreas Roodt ^c

^aRadiochemistry, South African Nuclear Energy Corporation Ltd (Necsa), PO Box 582, Pretoria 0001, South Africa, ^bCARST, Northwest University, Mafikeng Campus, Private bag X2046, Mmabatho, 2735, South Africa, and ^cDepartment of Chemistry, University of the Free State, PO Box 339, Bloemfontein 9300, South Africa
^*Correspondence e-mail: visserhg.sci@mail.uovs.ac.za

(Received 12 July 2010; accepted 20 July 2010; online 31 July 2010)

In the title compound, (C₈H₂₀N)[Re(C₉H₅N₂O₂)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 interactions 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_r = 609.08
Triclinic, $[P \overline 1]$
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[F² > 2σ(F²)] = 0.027
wR(F²) = 0.065
S = 1.07
5458 reflections
275 parameters
12 restraints
H-atom parameters constrained
Δρ_max = 1.74 e Å⁻³
Δρ_min = −1.04 e Å⁻³

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) x, y+1, z.

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 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S160053681002893X/pv2307sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S160053681002893X/pv2307Isup2.hkl

checkCIF report

Comment top

The title complex, (C₈H₂₀N)[Re(C₉H₅N₂O₂)Cl(CO)₃], forms a part of an ongoing investigation of the structural and kinetic behaviour of fac-Re(CO)₃ compounds (Schutte et al., (2008); Wang et al., (2003); Alvarez et al., (2007); Brasey et al., (2004); Suthiram et al., (2009)). It crystallized as an anionic Re^I compound and one tetraethylammonium counter ion in the asymmetric unit (Fig. 1). The Re—CO bond distances are well within the normal range (Allen et al., 1987). The small bite angle O4—Re1—N1 of 74.71 (11) ° might be a reason for the distorted octahedral geometry around the metal centre. The crystal packing is controlled by C—H···O hydrogen bonding and π - π -stacking interactions involving the benzene rings, with a centroid-centroid distance of 3.4220 (1) Å (Fig. 2).

Related literature top

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 top

[NEt₄]₂[Re(CO)₃Cl₃] (150 mg, 0.235 mmol) was added to 30 ml me thanol to result in a suspension which was heated for a few minutes until the solution turned clear. Quinoxaline-2-carbaldehyde (41 mg, 0.235 mmol) was dissolved in 5 ml me thanol and slowly added to the reaction solution whilst stirring. K₂CO₃ (16.6 mg, 0.120 mmol) was added to the solution. The dark orange solution that formed was refluxed for 4 h after which the solvent was evaporated completely on a rotoevaporator. The resulting solid was redissolved in a minimum volume of dichloromethane, layered with diethyl ether and left to stand in a refrigerator. After several days red crystals suitable for X-ray diffraction were isolated. (Yield: 56 mg, 39%).

Structure description top

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).

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: 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).

Figures top

	Fig. 1. Molecular structure of the title compound. Displacement ellipsoids are drawn at the 50% probability displacement level.
	Fig. 2. π-π -Stacking interactions of the title compound; cations have been omitted for clarity.

Tetraethylammonium tricarbonylchlorido(quinoxaline-2- carboxylato-κ²N¹,O)rhenate(I) top

Crystal data top

(C₈H₂₀N)[Re(C₉H₅N₂O₂)Cl(CO)₃]	Z = 2
M_r = 609.08	F(000) = 596
Triclinic, P1	D_x = 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

Data collection top

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

Refinement top

Refinement on F²	12 restraints
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.027	w = 1/[σ²(F_o²) + (0.0211P)² + 1.8438P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.065	(Δ/σ)_max = 0.003
S = 1.07	Δρ_max = 1.74 e Å⁻³
5458 reflections	Δρ_min = −1.04 e Å⁻³
275 parameters

Crystal data top

(C₈H₂₀N)[Re(C₉H₅N₂O₂)Cl(CO)₃]	γ = 90.686 (5)°
M_r = 609.08	V = 1102.3 (9) Å³
Triclinic, P1	Z = 2
a = 8.402 (5) Å	Mo Kα radiation
b = 10.077 (5) Å	µ = 5.67 mm⁻¹
c = 13.495 (5) Å	T = 100 K
α = 97.433 (5)°	0.33 × 0.29 × 0.20 mm
β = 103.141 (5)°

Data collection top

Bruker X8 APEXII 4K Kappa CCD diffractometer	5458 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2004)	4988 reflections with I > 2σ(I)
T_min = 0.169, T_max = 0.324	R_int = 0.054
22501 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.027	12 restraints
wR(F²) = 0.065	H-atom parameters constrained
S = 1.07	Δρ_max = 1.74 e Å⁻³
5458 reflections	Δρ_min = −1.04 e Å⁻³
275 parameters

Special details top

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
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) x, y+1, z.

Experimental details

Crystal data
Chemical formula	(C₈H₂₀N)[Re(C₉H₅N₂O₂)Cl(CO)₃]
M_r	609.08
Crystal system, space group	Triclinic, P1
Temperature (K)	100
a, b, c (Å)	8.402 (5), 10.077 (5), 13.495 (5)
α, β, γ (°)	97.433 (5), 103.141 (5), 90.686 (5)
V (Å³)	1102.3 (9)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	5.67
Crystal size (mm)	0.33 × 0.29 × 0.20

Data collection
Diffractometer	Bruker X8 APEXII 4K Kappa CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2004)
T_min, T_max	0.169, 0.324
No. of measured, independent and observed [I > 2σ(I)] reflections	22501, 5458, 4988
R_int	0.054
(sin θ/λ)_max (Å⁻¹)	0.668

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.027, 0.065, 1.07
No. of reflections	5458
No. of parameters	275
No. of restraints	12
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.74, −1.04

Computer programs: APEX2 (Bruker, 2005), SAINT-Plus (Bruker, 2004), SAINT-Plus and XPREP (Bruker, 2004), SIR97 (Altomare et al., 1999), SHELXL97 (Sheldrick, 2008), DIAMOND (Brandenburg & Putz, 2005), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top

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) x, y+1, z.

Acknowledgements

The authors wish to thank Necsa and the UFS for funding and permission to publish this work.

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