trans-Dichloridobis(3,5-dimethyl­pyridine-κN)(ethano­lato-κO)oxido­rhenium(V)

Skarżyńska, A.; Trzeciak, A.M.; Gniewek, A.

doi:10.1107/S1600536811029588

metal-organic compounds

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ISSN: 2056-9890

Volume 67| Part 8| August 2011| Pages m1154-m1155

doi:10.1107/S1600536811029588

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trans-Dichloridobis(3,5-dimethylpyridine-κN)(ethanolato-κO)oxidorhenium(V)

Anna Skarżyńska,^a Anna M. Trzeciak ^a and Andrzej Gniewek ^a ^*

^aFaculty of Chemistry, University of Wrocław, 14 F. Joliot-Curie, 50-383 Wrocław, Poland
^*Correspondence e-mail: andrzej@netesa.com

(Received 20 July 2011; accepted 21 July 2011; online 30 July 2011)

The title compound, [Re(C₂H₅O)Cl₂O(C₇H₉N)₂], was crystallized from ethanol. The crystal structure of this complex contains a Re(V) atom in a slightly distorted octahedral coordination geometry with pairs of equivalent ligands in trans positions. Adjacent complex molecules are linked by weak C—H⋯Cl hydrogen bonds. The crystal structure is additionally stabilized by π–π stacking interactions between the aromatic rings with centroid–centroid distances of 3.546 (4) Å.

Related literature

The structure of the title compound was determined as part of a larger study on rhenium chemistry. For related structures and further discussion, see: Fortin & Beauchamp (1998 ); Iengo et al. (2001 ); Lock & Turner (1977 ). For hydrogen-bond interactions, see: Aullón et al. (1998 ); Bernstein et al. (1995 ); Desiraju & Steiner (1999 ) and for π–π stacking contacts, see: McGaughey et al. (1998 ). For details of the temperature control applied during data collection, see: Cosier & Glazer (1986 ) and for specifications of the analytical numeric absorption correction, see: Clark & Reid (1995 ).

Experimental

Crystal data

[Re(C₂H₅O)Cl₂O(C₇H₉N)₂]
M_r = 532.46
Triclinic, $[P \overline 1]$
a = 8.782 (2) Å
b = 9.458 (2) Å
c = 12.022 (3) Å
α = 76.71 (3)°
β = 70.84 (3)°
γ = 73.21 (3)°
V = 892.9 (4) Å³
Z = 2
Mo Kα radiation
μ = 7.11 mm⁻¹
T = 90 K
0.14 × 0.10 × 0.08 mm

Data collection

Oxford Diffraction Xcalibur PX diffractometer with CCD detector
Absorption correction: analytical (CrysAlis RED; Oxford Diffraction, 2010 $[Oxford Diffraction (2010). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Wrocław, Poland.]$ ) T_min = 0.522, T_max = 0.608
9213 measured reflections
3992 independent reflections
3519 reflections with I > 2σ(I)
R_int = 0.039

Refinement

R[F² > 2σ(F²)] = 0.021
wR(F²) = 0.043
S = 0.96
3992 reflections
213 parameters
H-atom parameters constrained
Δρ_max = 0.89 e Å⁻³
Δρ_min = −0.69 e Å⁻³

Table 1
Selected geometric parameters (Å, °)

Re—O1	1.698 (2)
Re—O2	1.882 (2)
Re—Cl1	2.4360 (11)
Re—Cl2	2.3728 (11)
Re—N1	2.143 (3)
Re—N2	2.132 (3)

O1—Re—O2	171.57 (10)
N1—Re—N2	177.79 (10)
Cl1—Re—Cl2	173.74 (3)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C121—H12C⋯Cl1ⁱ	0.98	2.82	3.754 (4)	160
C13—H13⋯Cl1ⁱ	0.95	2.92	3.717 (4)	142
Symmetry code: (i) x-1, y, z.

Data collection: CrysAlis CCD (Oxford Diffraction, 2010 $[Oxford Diffraction (2010). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Wrocław, Poland.]$ ); cell refinement: CrysAlis RED (Oxford Diffraction, 2010 $[Oxford Diffraction (2010). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Wrocław, Poland.]$ ); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811029588/bt5584sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811029588/bt5584Isup2.hkl

checkCIF report

Comment top

Complexes of the ReO(OR)X₂L₂ type (where R is an alkyl group, X is a halogen and L is an N-donor ligand or monodendate phosphine) are commonly used as precursors for other Re(V) species, such as dioxo mononuclear and dinuclear compounds (Fortin & Beauchamp, 1998). When L is a diaza ligand, they might also be applied for the construction of multi-metal supramolecular assemblies (Iengo et al., 2001). Normally, these complexes are obtained as the all trans isomers (Lock & Turner, 1977). In this paper we report the synthesis procedure and crystal structure of an oxorhenium(V) complex with 3,5-dimethylpyridine ligands, the title compound.

The environment around the metal center is a slightly distorted octahedron with two chloro ligands, two 3,5-dimethylpyridine ligands, ethoxo and oxo ligands, all in trans positions to each other (Fig. 1). The observed Re—ligand bond distances (Table 1) are similar to the reported for analogous complexes of the ReO(OR)X₂L₂ type. However, the distortion of the angles in the coordination sphere of the Re atom is more significant than in similar compounds. Especially, the O1—Re—O2 and Cl1—Re—Cl2 angles differ from the expected value of 180°.

In the crystal structure, the molecules of the title complex are linked by a few weak hydrogen interactions of the C—H···Cl type (Desiraju & Steiner, 1999). The C13 and C121 atoms act as hydrogen-bond donors to Cl1ⁱ [symmetry code: (i) x – 1, y, z] as an acceptor (Table 2). The observed C—H···Cl distances are similar to the values of the N—H···Cl hydrogen bonds identified for Cl bonded to a transition metal (Aullón et al., 1998). Each of the molecules accepts two hydrogen bonds and also donates two hydrogen bonds (Fig. 2), thus forming a C(7)C(7)[R₂¹(6)] chain of rings motif (Bernstein et al., 1995).

Additionally, the N1/C11–C15 and N2/C21–C25 rings are engaged in π-π stacking contacts (Fig. 2), which further assist in the stabilization of the crystal structure by assembling chains running parallel to the [100] direction. The distance of the centroids and the offset of the pyridine rings (Table 3) are typical for energetically favorable non-bonded aromatic interactions (McGaughey et al., 1998).

Related literature top

The structure of the title compound was determined as part of a larger study on rhenium chemistry. For related structures and further discussion, see: Fortin & Beauchamp (1998); Iengo et al. (2001); Lock & Turner (1977). For hydrogen-bond interactions, see: Aullón et al. (1998); Bernstein et al. (1995); Desiraju & Steiner (1999) and for π–π stacking contacts, see: McGaughey et al. (1998). For details of the temperature control applied during data collection, see: Cosier & Glazer (1986) and for specifications of the analytical numeric absorption correction, see: Clark & Reid (1995).

Experimental top

The title compound was prepared similarly to the previously reported rhenium(V) complex with pyrazine ligands (Iengo et al., 2001). 3,5-dimethylpyridine (0.55 ml, 4.77 mmol) was added to the suspension of ReOCl₃(OPPh₃)(SMe₂) (1.0 g, 1.54 mmol) in absolute ethanol (10 ml). The mixture was heated under reflux for 1 h, forming dark blue solution. Upon cooling down, crystalline precipitate appeared in the system. It was filtered off, washed with ethanol and diethyl ether. Finally, the product was dried in vacuo. Yield: 0.70 g, 85%. Analysis calculated: C 36.09, H 4.35, N 5.26%; found: C 36.04, H 4.23, N 5.25%. IR (KBr, cm^-1): δ(OCH₂) 915 (versus), ν(Re=O) 960 (versus). ¹H NMR (CDCl₃): δ 1.00 (3H, t, ³J = 6.9 Hz, CH₃), 2.32 (12H, s, CH₃) 3.75 (2H, q, ³J = 6.9 Hz, CH₂), 7.34 (2H, s, CH), 8.48 (4H, s, CH).

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2010); cell refinement: CrysAlis RED (Oxford Diffraction, 2010); data reduction: CrysAlis RED (Oxford Diffraction, 2010); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure and atom numbering scheme of the title compound. Displacement ellipsoids are drawn at the 30% probability level and H atoms are shown as small spheres of arbitrary radii.

Fig. 2. The arrangement of the molecules in the crystal structure, a perspective view in an oblique direction. Weak intermolecular hydrogen bonds are represented by dashed lines and the π-π stacking interactions by dotted lines. Cg1 and Cg2 denote the centroids of the N1/C11—C15 and N2/C21—C25 pyridine rings, respectively. For clarity, H atoms that are not involved in the discussed interactions have been omitted. [Symmetry codes: (i) x - 1, y, z; (ii) x + 1, y, z.]

trans-Dichloridobis(3,5-dimethylpyridine- κN)(ethanolato-κO)oxidorhenium(V) top

Crystal data top

[Re(C₂H₅O)Cl₂O(C₇H₉N)₂]	Z = 2
M_r = 532.46	F(000) = 516
Triclinic, P1	D_x = 1.980 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.782 (2) Å	Cell parameters from 6128 reflections
b = 9.458 (2) Å	θ = 5.0–27.5°
c = 12.022 (3) Å	µ = 7.11 mm⁻¹
α = 76.71 (3)°	T = 90 K
β = 70.84 (3)°	Block, dark blue
γ = 73.21 (3)°	0.14 × 0.10 × 0.08 mm
V = 892.9 (4) Å³

Data collection top

Oxford Diffraction Xcalibur PX diffractometer with CCD detector	3992 independent reflections
Radiation source: fine-focus sealed tube	3519 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.039
ϕ and ω scans	θ_max = 27.5°, θ_min = 5.0°
Absorption correction: analytical (CrysAlis RED; Oxford Diffraction, 2010)	h = −11→8
T_min = 0.522, T_max = 0.608	k = −12→12
9213 measured reflections	l = −15→15

Refinement top

Refinement on F²	Primary atom site location: heavy-atom method
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.021	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.043	H-atom parameters constrained
S = 0.96	w = 1/[σ²(F_o²) + (0.0155P)²] where P = (F_o² + 2F_c²)/3
3992 reflections	(Δ/σ)_max = 0.001
213 parameters	Δρ_max = 0.89 e Å⁻³
0 restraints	Δρ_min = −0.69 e Å⁻³

Crystal data top

[Re(C₂H₅O)Cl₂O(C₇H₉N)₂]	γ = 73.21 (3)°
M_r = 532.46	V = 892.9 (4) Å³
Triclinic, P1	Z = 2
a = 8.782 (2) Å	Mo Kα radiation
b = 9.458 (2) Å	µ = 7.11 mm⁻¹
c = 12.022 (3) Å	T = 90 K
α = 76.71 (3)°	0.14 × 0.10 × 0.08 mm
β = 70.84 (3)°

Data collection top

Oxford Diffraction Xcalibur PX diffractometer with CCD detector	3992 independent reflections
Absorption correction: analytical (CrysAlis RED; Oxford Diffraction, 2010)	3519 reflections with I > 2σ(I)
T_min = 0.522, T_max = 0.608	R_int = 0.039
9213 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.021	0 restraints
wR(F²) = 0.043	H-atom parameters constrained
S = 0.96	Δρ_max = 0.89 e Å⁻³
3992 reflections	Δρ_min = −0.69 e Å⁻³
213 parameters

Special details top

Experimental. The crystal was placed in the cold stream of an open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 90 K. Analytical numeric absorption correction was carried out with CrysAlis RED (Oxford Diffraction, 2010) using a multifaceted crystal model (Clark & Reid, 1995).

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.

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Re	0.631394 (17)	0.243503 (16)	0.216648 (12)	0.00894 (4)
Cl1	0.77034 (10)	−0.01144 (9)	0.27897 (7)	0.01403 (17)
Cl2	0.48876 (10)	0.49592 (9)	0.17785 (7)	0.01358 (17)
O1	0.6619 (3)	0.1964 (3)	0.0816 (2)	0.0130 (5)
O2	0.5921 (3)	0.2674 (3)	0.37560 (19)	0.0115 (5)
N1	0.4009 (3)	0.1765 (3)	0.2774 (2)	0.0104 (6)
N2	0.8601 (3)	0.3103 (3)	0.1631 (2)	0.0101 (6)
C1	0.5564 (4)	0.1947 (4)	0.4951 (3)	0.0136 (7)
H1A	0.6603	0.1316	0.5120	0.016*
H1B	0.4811	0.1290	0.5067	0.016*
C2	0.4763 (5)	0.3073 (4)	0.5805 (3)	0.0188 (8)
H2A	0.5537	0.3681	0.5727	0.028*
H2B	0.4476	0.2549	0.6623	0.028*
H2C	0.3756	0.3721	0.5621	0.028*
C11	0.3875 (4)	0.0612 (4)	0.2362 (3)	0.0106 (7)
H11	0.4825	0.0094	0.1829	0.013*
C12	0.2406 (4)	0.0147 (4)	0.2683 (3)	0.0112 (7)
C13	0.1050 (4)	0.0892 (4)	0.3481 (3)	0.0114 (7)
H13	0.0028	0.0598	0.3719	0.014*
C14	0.1167 (4)	0.2065 (4)	0.3940 (3)	0.0121 (7)
C15	0.2686 (4)	0.2471 (4)	0.3544 (3)	0.0107 (7)
H15	0.2783	0.3285	0.3834	0.013*
C121	0.2334 (4)	−0.1124 (4)	0.2158 (3)	0.0150 (7)
H12A	0.2820	−0.2074	0.2582	0.022*
H12B	0.2960	−0.1038	0.1314	0.022*
H12C	0.1178	−0.1087	0.2237	0.022*
C141	−0.0273 (4)	0.2905 (4)	0.4818 (3)	0.0182 (8)
H14A	−0.1294	0.2644	0.4860	0.027*
H14B	−0.0380	0.3981	0.4559	0.027*
H14C	−0.0080	0.2636	0.5606	0.027*
C21	0.8737 (4)	0.4278 (4)	0.2016 (3)	0.0103 (7)
H21	0.7792	0.4800	0.2549	0.012*
C22	1.0199 (4)	0.4760 (4)	0.1666 (3)	0.0102 (7)
C23	1.1549 (4)	0.4001 (4)	0.0868 (3)	0.0107 (7)
H23	1.2563	0.4313	0.0603	0.013*
C24	1.1439 (4)	0.2788 (4)	0.0452 (3)	0.0107 (7)
C25	0.9937 (4)	0.2371 (4)	0.0874 (3)	0.0126 (7)
H25	0.9848	0.1529	0.0615	0.015*
C221	1.0287 (4)	0.6068 (4)	0.2129 (3)	0.0157 (7)
H22A	1.1026	0.5727	0.2645	0.024*
H22B	0.9176	0.6537	0.2586	0.024*
H22C	1.0716	0.6796	0.1459	0.024*
C241	1.2877 (4)	0.1938 (4)	−0.0404 (3)	0.0147 (7)
H24A	1.2542	0.1140	−0.0594	0.022*
H24B	1.3792	0.1501	−0.0042	0.022*
H24C	1.3239	0.2616	−0.1135	0.022*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Re	0.00818 (7)	0.00968 (7)	0.00966 (7)	−0.00304 (5)	−0.00212 (5)	−0.00210 (5)
Cl1	0.0115 (4)	0.0100 (4)	0.0204 (4)	−0.0022 (3)	−0.0049 (3)	−0.0020 (3)
Cl2	0.0124 (4)	0.0107 (4)	0.0170 (4)	−0.0025 (3)	−0.0045 (3)	−0.0006 (3)
O1	0.0115 (12)	0.0156 (12)	0.0131 (12)	−0.0047 (10)	−0.0018 (10)	−0.0049 (10)
O2	0.0126 (12)	0.0117 (11)	0.0110 (11)	−0.0035 (10)	−0.0044 (10)	−0.0007 (10)
N1	0.0112 (15)	0.0110 (14)	0.0105 (13)	−0.0018 (12)	−0.0063 (12)	−0.0006 (11)
N2	0.0107 (14)	0.0111 (14)	0.0092 (13)	−0.0032 (12)	−0.0037 (11)	−0.0010 (11)
C1	0.0151 (18)	0.0121 (17)	0.0105 (16)	−0.0037 (15)	−0.0010 (14)	0.0012 (14)
C2	0.025 (2)	0.0162 (18)	0.0134 (17)	−0.0051 (16)	−0.0011 (16)	−0.0042 (15)
C11	0.0105 (17)	0.0099 (16)	0.0103 (16)	−0.0013 (14)	−0.0032 (13)	−0.0005 (13)
C12	0.0132 (18)	0.0108 (16)	0.0118 (16)	−0.0045 (14)	−0.0068 (14)	0.0011 (14)
C13	0.0102 (17)	0.0127 (16)	0.0102 (16)	−0.0035 (14)	−0.0015 (14)	−0.0009 (14)
C14	0.0098 (17)	0.0140 (17)	0.0112 (16)	−0.0013 (14)	−0.0022 (14)	−0.0025 (14)
C15	0.0114 (17)	0.0095 (16)	0.0110 (16)	0.0003 (14)	−0.0055 (14)	−0.0010 (13)
C121	0.0136 (18)	0.0126 (17)	0.0197 (18)	−0.0048 (15)	−0.0018 (15)	−0.0063 (15)
C141	0.0164 (19)	0.0175 (18)	0.0202 (19)	−0.0063 (16)	0.0004 (15)	−0.0069 (16)
C21	0.0108 (17)	0.0114 (16)	0.0079 (15)	−0.0013 (14)	−0.0031 (13)	−0.0009 (13)
C22	0.0136 (17)	0.0088 (16)	0.0098 (15)	−0.0038 (14)	−0.0068 (14)	0.0027 (13)
C23	0.0075 (17)	0.0117 (16)	0.0126 (16)	−0.0036 (14)	−0.0020 (14)	−0.0008 (14)
C24	0.0139 (18)	0.0105 (16)	0.0076 (15)	−0.0037 (14)	−0.0053 (14)	0.0031 (13)
C25	0.0160 (18)	0.0117 (16)	0.0118 (16)	−0.0042 (15)	−0.0051 (14)	−0.0022 (14)
C221	0.0169 (19)	0.0142 (17)	0.0196 (18)	−0.0047 (15)	−0.0075 (15)	−0.0047 (15)
C241	0.0142 (18)	0.0167 (18)	0.0133 (17)	−0.0065 (15)	−0.0004 (14)	−0.0042 (15)

Geometric parameters (Å, º) top

Re—O1	1.698 (2)	C14—C141	1.508 (5)
Re—O2	1.882 (2)	C15—H15	0.9500
Re—Cl1	2.4360 (11)	C121—H12A	0.9800
Re—Cl2	2.3728 (11)	C121—H12B	0.9800
Re—N1	2.143 (3)	C121—H12C	0.9800
Re—N2	2.132 (3)	C141—H14A	0.9800
O2—C1	1.418 (4)	C141—H14B	0.9800
N1—C15	1.334 (4)	C141—H14C	0.9800
N1—C11	1.345 (4)	C21—C22	1.389 (4)
N2—C25	1.343 (4)	C21—H21	0.9500
N2—C21	1.346 (4)	C22—C23	1.385 (4)
C1—C2	1.510 (5)	C22—C221	1.500 (5)
C1—H1A	0.9900	C23—C24	1.392 (4)
C1—H1B	0.9900	C23—H23	0.9500
C2—H2A	0.9800	C24—C25	1.387 (4)
C2—H2B	0.9800	C24—C241	1.497 (5)
C2—H2C	0.9800	C25—H25	0.9500
C11—C12	1.390 (4)	C221—H22A	0.9800
C11—H11	0.9500	C221—H22B	0.9800
C12—C13	1.383 (4)	C221—H22C	0.9800
C12—C121	1.504 (5)	C241—H24A	0.9800
C13—C14	1.389 (4)	C241—H24B	0.9800
C13—H13	0.9500	C241—H24C	0.9800
C14—C15	1.397 (4)

O1—Re—N1	88.90 (10)	C13—C14—C141	122.6 (3)
O2—Re—N1	85.89 (10)	C15—C14—C141	120.0 (3)
O1—Re—N2	93.24 (10)	N1—C15—C14	122.8 (3)
O2—Re—N2	91.92 (10)	N1—C15—H15	118.6
O1—Re—O2	171.57 (10)	C14—C15—H15	118.6
N1—Re—N2	177.79 (10)	C12—C121—H12A	109.5
O1—Re—Cl1	88.90 (8)	C12—C121—H12B	109.5
O2—Re—Cl1	84.42 (8)	H12A—C121—H12B	109.5
N1—Re—Cl1	89.20 (8)	C12—C121—H12C	109.5
N2—Re—Cl1	90.33 (8)	H12A—C121—H12C	109.5
O1—Re—Cl2	97.31 (8)	H12B—C121—H12C	109.5
O2—Re—Cl2	89.33 (8)	C14—C141—H14A	109.5
N1—Re—Cl2	90.07 (8)	C14—C141—H14B	109.5
N2—Re—Cl2	90.16 (8)	H14A—C141—H14B	109.5
Cl1—Re—Cl2	173.74 (3)	C14—C141—H14C	109.5
C1—O2—Re	144.0 (2)	H14A—C141—H14C	109.5
C15—N1—C11	118.7 (3)	H14B—C141—H14C	109.5
C15—N1—Re	121.9 (2)	N2—C21—C22	122.7 (3)
C11—N1—Re	119.4 (2)	N2—C21—H21	118.6
C25—N2—C21	118.5 (3)	C22—C21—H21	118.6
C25—N2—Re	120.2 (2)	C23—C22—C21	117.6 (3)
C21—N2—Re	121.3 (2)	C23—C22—C221	121.8 (3)
O2—C1—C2	110.8 (3)	C21—C22—C221	120.6 (3)
O2—C1—H1A	109.5	C22—C23—C24	120.8 (3)
C2—C1—H1A	109.5	C22—C23—H23	119.6
O2—C1—H1B	109.5	C24—C23—H23	119.6
C2—C1—H1B	109.5	C25—C24—C23	117.3 (3)
H1A—C1—H1B	108.1	C25—C24—C241	120.5 (3)
C1—C2—H2A	109.5	C23—C24—C241	122.2 (3)
C1—C2—H2B	109.5	N2—C25—C24	123.0 (3)
H2A—C2—H2B	109.5	N2—C25—H25	118.5
C1—C2—H2C	109.5	C24—C25—H25	118.5
H2A—C2—H2C	109.5	C22—C221—H22A	109.5
H2B—C2—H2C	109.5	C22—C221—H22B	109.5
N1—C11—C12	122.7 (3)	H22A—C221—H22B	109.5
N1—C11—H11	118.7	C22—C221—H22C	109.5
C12—C11—H11	118.7	H22A—C221—H22C	109.5
C13—C12—C11	117.7 (3)	H22B—C221—H22C	109.5
C13—C12—C121	122.5 (3)	C24—C241—H24A	109.5
C11—C12—C121	119.8 (3)	C24—C241—H24B	109.5
C12—C13—C14	120.6 (3)	H24A—C241—H24B	109.5
C12—C13—H13	119.7	C24—C241—H24C	109.5
C14—C13—H13	119.7	H24A—C241—H24C	109.5
C13—C14—C15	117.4 (3)	H24B—C241—H24C	109.5

N2—Re—O2—C1	−125.9 (4)	N1—C11—C12—C13	−1.6 (5)
N1—Re—O2—C1	53.9 (4)	N1—C11—C12—C121	178.2 (3)
Cl2—Re—O2—C1	144.0 (3)	C11—C12—C13—C14	0.1 (5)
Cl1—Re—O2—C1	−35.7 (3)	C121—C12—C13—C14	−179.7 (3)
O1—Re—N1—C15	−145.0 (2)	C12—C13—C14—C15	1.3 (5)
O2—Re—N1—C15	41.7 (2)	C12—C13—C14—C141	−179.6 (3)
Cl2—Re—N1—C15	−47.7 (2)	C11—N1—C15—C14	0.0 (4)
Cl1—Re—N1—C15	126.1 (2)	Re—N1—C15—C14	179.2 (2)
O1—Re—N1—C11	34.2 (2)	C13—C14—C15—N1	−1.3 (5)
O2—Re—N1—C11	−139.2 (2)	C141—C14—C15—N1	179.5 (3)
Cl2—Re—N1—C11	131.5 (2)	C25—N2—C21—C22	−0.2 (4)
Cl1—Re—N1—C11	−54.7 (2)	Re—N2—C21—C22	−178.7 (2)
O1—Re—N2—C25	−35.3 (2)	N2—C21—C22—C23	1.3 (4)
O2—Re—N2—C25	138.1 (2)	N2—C21—C22—C221	−179.5 (3)
Cl2—Re—N2—C25	−132.6 (2)	C21—C22—C23—C24	−0.9 (5)
Cl1—Re—N2—C25	53.7 (2)	C221—C22—C23—C24	179.9 (3)
O1—Re—N2—C21	143.2 (2)	C22—C23—C24—C25	−0.5 (5)
O2—Re—N2—C21	−43.4 (2)	C22—C23—C24—C241	−179.6 (3)
Cl2—Re—N2—C21	45.9 (2)	C21—N2—C25—C24	−1.3 (4)
Cl1—Re—N2—C21	−127.9 (2)	Re—N2—C25—C24	177.2 (2)
Re—O2—C1—C2	−157.5 (3)	C23—C24—C25—N2	1.6 (5)
C15—N1—C11—C12	1.5 (4)	C241—C24—C25—N2	−179.2 (3)
Re—N1—C11—C12	−177.7 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C121—H12C···Cl1ⁱ	0.98	2.82	3.754 (4)	160
C13—H13···Cl1ⁱ	0.95	2.92	3.717 (4)	142

Symmetry code: (i) x−1, y, z.

Experimental details

Crystal data
Chemical formula	[Re(C₂H₅O)Cl₂O(C₇H₉N)₂]
M_r	532.46
Crystal system, space group	Triclinic, P1
Temperature (K)	90
a, b, c (Å)	8.782 (2), 9.458 (2), 12.022 (3)
α, β, γ (°)	76.71 (3), 70.84 (3), 73.21 (3)
V (Å³)	892.9 (4)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	7.11
Crystal size (mm)	0.14 × 0.10 × 0.08

Data collection
Diffractometer	Oxford Diffraction Xcalibur PX diffractometer with CCD detector
Absorption correction	Analytical (CrysAlis RED; Oxford Diffraction, 2010)
T_min, T_max	0.522, 0.608
No. of measured, independent and observed [I > 2σ(I)] reflections	9213, 3992, 3519
R_int	0.039
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.021, 0.043, 0.96
No. of reflections	3992
No. of parameters	213
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.89, −0.69

Computer programs: CrysAlis CCD (Oxford Diffraction, 2010), CrysAlis RED (Oxford Diffraction, 2010), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997).

Selected geometric parameters (Å, º) top

Re—O1	1.698 (2)	Re—Cl2	2.3728 (11)
Re—O2	1.882 (2)	Re—N1	2.143 (3)
Re—Cl1	2.4360 (11)	Re—N2	2.132 (3)

O1—Re—O2	171.57 (10)	Cl1—Re—Cl2	173.74 (3)
N1—Re—N2	177.79 (10)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C121—H12C···Cl1ⁱ	0.98	2.82	3.754 (4)	160
C13—H13···Cl1ⁱ	0.95	2.92	3.717 (4)	142

Symmetry code: (i) x−1, y, z.

Intermolecular π-π interactions (Å, °). top

CgI	CgJ	Cg···Cg	Dihedral angle	Interplanar distance	Offset
1	2ⁱ	3.546 (4)	2.0 (3)	3.381 (4)	1.069 (4)
2	1ⁱⁱ	3.546 (4)	2.0 (3)	3.362 (4)	1.127 (4)

Cg1 denotes the centroid of ring N1/C11-C15; Cg2 of ring N2/C21-C25. Cg···Cg is the distance between ring centroids. The dihedral plane is that between the CgI and CgJ planes. The interplanar distance is the perpendicular distance of CgI from ring J plane. The offset is the lateral displacement of ring I relative to ring J.

Symmetry codes: (i) x-1, y, z; (ii) x+1, y, z.

Acknowledgements

This work was partially supported by the Polish Ministry of Science and Higher Education through grant No. N204 028538. The financial support is gratefully acknowledged.

References

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