Two fac-tri­carbonyl­rhenium(I) aza­dipyrromethene (ADPM) complexes: ligand-substitution effect on crystal structure

The crystal structures of fac-(aceto­nitrile-[kappa]N)(2-{[3,5-bis­(4-meth­oxy­phen­yl)-2H-pyrrol-2-yl­idene-[kappa]N¹]amino}-3,5-bis­(4-meth­oxy­phen­yl)-1H-pyrrol-1-ido-[kappa]N¹)tricarbon­ylrhenium(I)-hexa­ne-aceto­nitrile (2/1/2), [Re(C₃₆H₃₀N₃O₄)(CH₃CN)(CO)₃]·0.5C₆H₁₄·CH₃CN, (2), and fac-(2-{[3,5-bis­(4-meth­oxy­phen­yl)-2H-pyrrol-2-yl­idene-[kappa]N¹]amino}-3,5-bis­(4-meth­oxy­phen­yl)-1H-pyrrol-1-ido-[kappa]N¹)tricarbon­yl(dimethyl sulfoxide-[kappa]O)rhenium(I), [Re(C₃₆H₃₀N₃O₄)(C₂H₆OS)(CO)₃], (3), at 150 K are reported. Both complexes display a distorted octa­hedral geometry, with a fac-Re(CO)₃ arrangement and one aza­dipyrromethene (ADPM) chelating ligand in the equatorial position. One solvent mol­ecule completes the coordination sphere of the Re^I centre in the remaining axial position. The ADPM ligand shows high flexibility upon coordination, while retaining its [pi]-delocalized nature. Bond length and angle analyses indicate that the differences in the geometry around the Re^I centre in (2) and (3), and those found in three reported fac-Re(CO)₃-ADPM complexes, are dictated mainly by steric factors and crystal packing. Both structures display intra­molecular C-H...N hydrogen bonding. Inter­molecular inter­actions of the Csp²-H...[pi] and Csp²-H...O(carbonyl) types link the discrete monomers into extended chains.

S1. Introduction

Aza­dipyrromethene (ADPM) organic dyes and related metal complexes (Co, Ni, Cu, Zn, Cr and Cd) with bidentate coordination motifs were first synthesized and patented for dyeing wool in the 1940s (Rogers, 1943a,b, 1946). The half-phthalocyanine structure of ADPM confers tunable photophysical properties in the far-red to near-IR (NIR) regions, while avoiding tedious macrocyclization and purification steps in its synthesis. The study of ADPM chromophore and its dipyrromethene (DPM) counterpart is therefore attracting much inter­est for light-harvesting applications (Bessette & Hanan, 2014; Khan et al., 2014; Wu et al., 2014; Berhe et al., 2014). The ADPM framework bearing a BF₂-chelate, namely the Aza-BODIPY derivative, also presents inter­esting fluorescence properties suitable for applications such as photodynamic therapy, fluorescent chemosensors and in vitro fluoro­phores in the NIR (Killoran et al., 2002; Loudet & Burgess, 2007; Coskun et al., 2007; Yuan et al., 2013; Wu & O'Shea, 2013; Lu et al., 2014; Collado et al., 2014). The exploration of transition-metal complexes incorporating ADPM ligands has been fuelled by their inter­esting spectroscopic properties and the possibility to fine tune them through ligand substitution. Luminescent three-coordinated complexes of group 11 (Cu^I, Ag^I and Au^I) metals bearing deprotonated bidentate ADPM and a phosphine ligand were reported first (Teets et al., 2007, 2009; Gao, Deligonul et al., 2012), followed by other examples where copper and silver chelates were incorporated a posteriori in ADPM–alt-p-phenyl­ene ethynylene conjugated polymers (Gao, Tang et al., 2012). Complexes of d⁸ metal centres (Rh^I, Ir^I, Pd^II and Pt^II) and d⁶ (Ir^III) were also reported where only one ADPM chromophore was coordinated (Deligonul & Gray, 2013; Deligonul et al., 2014). Four-coordinated homoleptic complexes of M^II centres (Co, Ni, Cu, Zn, Hg and Pd) bearing two chromophores were also studied in detail, presenting inter­esting potential for light-harvesting applications (Teets et al., 2008; Palma et al., 2009; Bessette et al., 2012; Senevirathna & Sauvé, 2013; McLean et al., 2014; Senevirathna et al., 2014; Jones et al., 2014). A heteroleptic version with both ADPM and DPM ligands on a Zn^II centre was reported to present fluorescence properties (Sakamoto et al., 2012). Finally, the family of fac-tri­carbonyl­rhenium(I)–ADPM complexes reported in the literature (Partyka et al., 2009) {[Re(ADPM)(L)(CO)₃], with L = pyridine (py), tert-butyl­iso­nitrile and tetra­hydro­tiophene (THT)} attracted our attention due to the presence of the labile coordination position perpendicular to the tetra­phenyl ADPM. In an extension to this work, we describe herein the solid-state structures of two new fac-tri­carbonyl­rhenium(I) ADPM complexes. The electron-rich ADPM (1) {see Scheme; systematic name: N-[3,5-bis­(4-meth­oxy­phenyl)-2H-pyrrol-2-yl­idene]-3,5-bis­(4-meth­oxy­phenyl)-1H-pyrrol-2-amine} is used to prepare the complexes [Re(ADPM)(ACN)(CO)₃].0.5C₆H₁₄.ACN, (2), and [Re(ADPM)(DMSO)(CO)₃], (3) (ACN is aceto­nitrile and DMSO is di­methyl sulfoxide). The ligand-substitution effect on crystal structure in this family of compounds is assessed by comparative analysis of (2), (3) and previously reported similar fac-Re(CO)₃ complexes (Partyka et al., 2009; Casanova et al., 2006; Chen et al., 2003; Zhao et al., 2013; Kia & Fun, 2008).

S2. Experimental

S2.1. Synthesis, crystallization and NMR data

S2.1.1. General procedure for the synthesis of (2) and (3)

A suspension of (1) (564 mg, 0.990 mmol, 1 equivalent), [Re(CO)₃(H₂O)₃]Br (400 mg, 0.990 mmol, 1 equivalent) and KO^tBu (111 mg, 0.990 mmol, 1 equivalent) in n-butanol (10 ml) was reacted in a microwave reactor for 3 h at 423 K under magnetic stirring. The reaction mixture was evaporated to dryness, dissolved in a minimum of di­chloro­methane and filtered. The solvent was evaporated and the resulting residue, presumably an inter­mediate stabilized by the coordination of n-butanol at the L position (see Scheme), was dissolved either in aceto­nitrile (ACN) for (2) or di­methyl sulfoxide (DMSO) for (3) (25 ml). The reaction mixture was heated at 348 K for 12 h, in order to exchange the n-butanol for the corresponding solvent, concentrated in vacuo, and a hot recrystallization was done to remove the unreacted ligand and salts. The solvent was removed in vacuo to afford a dark-purple solid. Diffraction-quality crystals of (2) (yield 603 mg, 69%) were obtained by slow diffusion of hexane in a concentrated di­chloro­methane solution of the complex. Crystals of (3) (yield 381 mg, 42%) suitable for X-ray diffraction studies were obtained with difficulty by slow diffusion of cyclo­hexane into a concentrated di­chloro­methane solution of the complex to which a drop of toluene was added.

S2.1.2. NMR data

For (2), ¹H NMR (CDCl₃, 400 MHz): δ 7.88–7.94 (m, 4H), 7.74–7.80 (m, 4H), 7.02–7.07 (m, 4H), 6.90–6.97 (m, 6H), 3.90 (s, 6H, meth­oxy), 3.89 (s, 6H, meth­oxy), 1.99 (s, 3H, coordinated ACN).

For (3), ¹H NMR (CDCl₃, 400 MHz): δ (ppm) 7.90 (d, J=8.8 Hz, 4H), 7.80 (d, J=8.8 Hz, 4H), 7.05 (d, J=8.8 Hz, 4H), 6.91-6.93 (m, 6H), 3.91 (s, 6H, meth­oxy), 3.88 (s, 6H, meth­oxy), 2.33 (s, 6H, coordinated DMSO).

S2.2. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 1. H atoms were included in calculated positions and treated as riding atoms, with aromatic C—H = 0.95 Å and methyl C—H = 0.98 Å, and with U_iso(H) = kU_iso(C), where k = 1.2 for the aromatic H atoms and 1.5 for the methyl H atoms.

The structure of (2) displays disorder at the level of the terminal meth­oxy substituents and the distal benzene rings, over two positions. The disordered benzene groups were constrained to an ideal hexagon, with C—C distances equal to 1.39 Å. The disorder was modelled as two components, with the occupation factors first refined, and then fixed at the values obtained after refinement (60:40 and 52:48 for the distal phenyl rings; 54:46 and 50:50 for the proximal meth­oxy groups). The model was refined anisotropically. Bond distance and mild displacement parameter (U^ij restraints were also applied to model the disordered moieties. Cocrystallized solvent (aceto­nitrile) was modelled in the same manner as described above, using in addition the EDAP instruction for the split N atom. The C—C distances were fixed at 1.529 (1) and 1.531 (1) Å in the model of the disordered cocrystallized hexane molecule on a symmetry position.

S3. Results and discussion

The molecular structures of (2) and (3) with the atom-numbering schemes are shown in Figs. 1 and 2, respectively. Selected geometric parameters are presented in Tables 2–4. Complex (2) crystallizes as black needles, with one independent molecule of the compound, one aceto­nitrile solvent molecule and half a hexane solvent molecule in the asymmetric unit. It exhibits disorder of the main molecule in the distal benzene rings and the terminal 4-meth­oxy groups of the ADPM ligand. The cocrystallized solvent (aceto­nitrile and hexane) is also disordered. Treatment of the disorder afforded an acceptable model (R1 = 0.0399) for discussion of bond lengths and angles in this comparative structural analysis. Complex (3) crystallizes as black blocks, with no cocrystallized solvent.

Both (2) and (3) show a distorted o­cta­hedral geometry at the metal centre, with a fac-Re(CO)₃ arrangement, one chelating ADPM ligand in the equatorial plane and the coordinated solvent molecule in the axial position. In (3), the DMSO molecule, trans to a carbonyl (strong π-acceptor) ligand, presents the κO coordination mode also found in [Re(DMSO)₃(CO)₃]⁺, [Re(DMSO)(py)₂(CO)₃]⁺ and [Re(bpy)(DMSO)(CO)₃]⁺ (Casanova et al., 2006).

The bond lengths and angles around the rhenium centres and the fac-Re(CO)₃ unit are comparable between the two structures (Table 2), and with those found in closely related structures of fac-[Re(ADPM)(L)(CO)₃] [where L = pyridine (py), tert-butyl­iso­nitrile and tetra­hydro­tiophene (THT)] (Partyka et al., 2009). Nevertheless, the Re1—C39 bond is significantly shorter in (3) than in (2). This situation is related to a higher degree of back-donation in complex (3) from the metal centre into the π*-orbitals of the carbonyl group, as also supported by the longer C39—O7 bond for (3) as compared to (2). A larger deviation from an o­cta­hedral geometry is observed in (3) versus (2) [N1—Re1—O8(DMSO) = 80.47 (10)° and N1—Re1—N4(ACN) = 84.63 (13)°], resulting from the necessity to accommodate the steric constraints of the DMSO molecule, and from crystal packing inter­actions [a weak C31(sp²)—H31···O8(DMSO) hydrogen bond is observed [H31···O8 = 2.69 Å, C31···O8 = 3.37 Å and C31—H31···O8 = 129 (1)°]. The N1—Re1—O8—S1 torsion angle of 60.6 (1)°, confirms the position of the DMSO ligand closer to the N1-side of the molecule. The bite angle N1—Re1—N3 of the ADPM ligand at 82.82 (11)° in (3) is similar to those found in [Re(ADPM)(py)(CO)₃] and [Re(ADPM)(THT)(CO)₃] (Partyka et al., 2009), but inferior to the value of 84.34 (14)° observed in (2).

It is important to note the axial C—O bonds that are trans to the coordinated solvent ligand are identical within 3σ in (2), (3) and the fac-[Re(CO)₃(ADPM)(L)] (L = py, tert-butyl­iso­nitrile and THT; Partyka et al., 2009). As such, the effect on the crystal structure of the σ-donation and/or π-acceptance capacity of the axial ligand cannot be determined. However, the fac-Re(CO)₃ unit presents C—O bond lengths in the range 1.146 (5)–1.160 (6) Å that are longer than in free CO (1.128 Å; Housecroft & Sharpe, 2012), as a result of back-donation from the rhenium in the carbonyl ligand π*-orbitals.

Consistent with the effect of the difference in charge density on the metal, the Re1—N4(ACN) bond distance in (2) [2.181 (4) Å] is similar within 3σ to those reported for the neutral complexes [Re(ACN)(L)(CO)₃] (L is an 8-oxyquinolate-type ligand; Zhao et al., 2013) and [Re(ACN)₂(tri­fluoro­acetato-kO)(CO)₃] (Kia & Fun, 2008), while being longer than in the cationic complex [Re(bpy)(ACN)(CO)₃]⁺ [bpy is ?,?'-bi­pyridine; 2.140 (3) Å; Chen et al., 2003]. The same type of comparison for (3) shows the Re1—O8(DMSO) bond [2.218 (3) Å] to be longer than in the corresponding cationic complex [Re(bpy)(DMSO)(CO)₃]⁺ (Casanova et al., 2006), as expected. In addition, the Re1—O8(DMSO) bond in (3) is longer than the Re1—N4(ACN) in (2), supporting the more labile nature of the DMSO ligand versus ACN.

Direct observations regarding the modification of ADPM ligand (1) upon complexation can be drawn from comparison of its solid-state structure (Bessette et al., 2012) and those of its rhenium complexes (2) and (3). The torsion of aryl substituents with respect to the ADPM core increases in order to accommodate the fac-Re(CO)₃ unit [tilt angles are in range 19.3 (1)–25.4 (1)° for (1) and 19.1 (1)–48.6 (1)° for (2) and (3), with the higher values corresponding to the tilt of the proximal aryl substituents]. The metal–chelate ring tilts with respect to the plane formed by the Re and the two equatorial carbonyl C atoms. This feature is common for all crystallographically charactherized fac-Re(ADPM)(CO)₃ complexes, and also for the ADPM complexes of metals with trigonal planar geometry (Teets et al., 2007). In (2) and (3), the values of these synclinal angles are 33.0 (1) and 37.9 (1)°, respectively, comparable with the range 34.4 (1)–39.8 (1)° observed for the other fac-Re(ADPM)(CO)₃ complexes (Partyka et al., 2009).

The synclinal angles between the planes of the pyrrole rings are also increased upon complexation. Even though the effect of π-delocalization remains dominant for this family of compounds independently of the deformation shown by the ligands upon complexation (Partyka et al., 2009), the periplanar angle of the pyrrole rings [8.5 (1)° in (2) and 5.1 (1)° in (3) versus 0.5 (1)° in (1)] correlates with bond length and angle modification in the ADPM ligand. In fact, a longer N1—C1 bond is observed in both (2) [1.403 (5) Å] and (3) [1.407 (4) Å] than the value of 1.374 (5) Å reported for free (1). In addition, larger C1—N2—C17 and N2—C17—N3 angles (Table 2) are found in both (2) [128.3 (4) and 127.4 (4)°] and (3) [127.3 (3) and 128.0 (3)°], as compared with (1) [121.1 (3) and 122.3 (3)°]. All these factors indicate a relatively high degree of flexibility and adaptability in the coordinated ADPM ligand, which represents an advantage over the structurally more rigid polypyridyl-type ligands.

Analysis of the packing in (2) and (3) reveals discrete monomers stacked in offset anti­parallel lines to accomodate the meth­oxy substituents and the tilted aryl rings (Figs. 3 and 4). Weak inter­molecular inter­actions link the molecules in extended chains throughout the crystal lattice. The results of hydrogen-bonding pattern analysis using PLATON (Spek, 2009) are presented in Table 3. It reveals nonclassical intra­molecular bifurcated acceptor Csp²—H···N hydrogen bonding (C6—H6···N2 and C22—H22···N2) (Desiraju & Steiner, 1999) and inter­molecular Csp²—H···O(carbonyl) inter­actions for (2). A simple intra­molecular Csp²—H···N hydrogen bond is identified in case of (3) (C22—H22···N2). The packing forces in both (2) and (3) are completed by weak inter­molecular Csp²—H···π(arene) hydrogen bonds (Table 3).

Computing details

For both compounds, data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2008); molecular graphics: OLEX2 (Dolomanov et al., 2009) and ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures

	Fig. 1. The molecular structure of (2), showing the atom-numbering scheme and with displacement ellipsoids drawn at the 50% probability level. H atoms (except those involved in hydrogen bonds), cocrystallized solvent and the minor-disorder components have been omitted for clarity.
	Fig. 2. The molecular structure of (3), showing the atom-numbering scheme and with displacement ellipsoids drawn at the 50% probability level. H atoms (except those involved in hydrogen bonds) have been omitted for clarity.
	Fig. 3. A packing diagram for (2), viewed along the a axis. Cocrystallized solvent and the minor-disorder components have been omitted for clarity.
	Fig. 4. A packing diagram for (3), viewed along the b axis.

(2) fac-(Acetonitrile-κN)(2-{[3,5-bis(4-methoxyphenyl)-2H-pyrrol-2-ylidene-κN¹]amino}-3,5-bis(4-methoxyphenyl)-1H-pyrrol-1-ido-κN¹)tricarbonylrhenium(I)–hexane–acetonitrile (2/1/2)

Crystal data

[Re(C36H30N3O4)(C2H3N)(CO)3]·0.5C6H14·C2H3N	F(000) = 1940
Mr = 964.05	Dx = 1.561 Mg m^−3
Monoclinic, P21/n	Cu Kα radiation, λ = 1.54178 Å
a = 12.4549 (3) Å	Cell parameters from 9330 reflections
b = 15.5837 (4) Å	θ = 3.5–70.6°
c = 21.1975 (5) Å	µ = 6.28 mm^−1
β = 94.5206 (11)°	T = 150 K
V = 4101.50 (17) Å^3	Needle, black
Z = 4	0.12 × 0.03 × 0.02 mm

Data collection

Bruker Microstar diffractometer	7834 independent reflections
Radiation source: Rotating Anode	7291 reflections with I > 2σ(I)
Detector resolution: 8.3 pixels mm^-1	Rint = 0.054
ω scans	θmax = 70.6°, θmin = 3.5°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −15→15
Tmin = 0.518, Tmax = 0.753	k = −19→19
88930 measured reflections	l = −24→25

Refinement

Refinement on F^2	786 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.040	H-atom parameters constrained
wR(F^2) = 0.106	w = 1/[σ^2(Fo^2) + (0.0559P)^2 + 8.6779P] where P = (Fo^2 + 2Fc^2)/3
S = 1.08	(Δ/σ)max = 0.001
7834 reflections	Δρmax = 1.60 e Å^−3
678 parameters	Δρmin = −0.90 e Å^−3

Special details

Experimental. Crystallographic data for the title compound were collected at 150 K, from single-crystal samples, which were mounted on a loop fiber. Data were collected using a Bruker Microstar diffractometer equipped with a Platinum 135 CCD Detector, a Helios optics and a Kappa goniometer. The crystal-to-detector distance was 3.8 cm, and the data collection was carried out in 512 x 512 pixel mode. The initial unit-cell parameters were determined by a least-squares fit of the angular setting of strong reflections, collected by a 110.0 degree scan in 110 frames over three different parts of the reciprocal space.

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 (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
Re1	0.11477 (2)	0.58734 (2)	0.28869 (2)	0.03598 (8)
O1	0.8039 (5)	0.3809 (6)	0.4823 (5)	0.056 (2)	0.6
O1A	0.8164 (6)	0.4086 (12)	0.4633 (8)	0.085 (5)	0.4
O2A	−0.1589 (7)	0.2045 (6)	0.2725 (8)	0.078 (4)	0.5
O2	−0.1864 (5)	0.2368 (6)	0.2746 (6)	0.055 (2)	0.5
O3	0.8070 (3)	0.7863 (3)	0.4839 (3)	0.0915 (15)
O4	−0.1621 (7)	0.9708 (6)	0.2862 (6)	0.082 (3)	0.52
O4A	−0.1839 (6)	0.9341 (6)	0.2693 (6)	0.067 (3)	0.48
O5	−0.0127 (5)	0.4581 (3)	0.2026 (2)	0.108 (2)
O6	−0.0758 (3)	0.5862 (3)	0.37134 (18)	0.0639 (11)
O7	−0.0111 (4)	0.7161 (3)	0.20213 (18)	0.0929 (16)
N1	0.2156 (3)	0.4926 (2)	0.34109 (16)	0.0387 (7)
N2	0.3680 (3)	0.5867 (2)	0.37115 (16)	0.0385 (8)
N3	0.2157 (3)	0.6810 (2)	0.34272 (16)	0.0367 (7)
N4	0.2425 (3)	0.58839 (19)	0.22397 (17)	0.0360 (7)
C1	0.3225 (3)	0.5106 (3)	0.3630 (2)	0.0421 (9)
C2	0.3784 (4)	0.4315 (3)	0.3783 (2)	0.0490 (11)
C3	0.3037 (3)	0.3674 (3)	0.3658 (2)	0.0470 (10)
H3	0.3159	0.3076	0.3711	0.056*
C4	0.2052 (4)	0.4068 (3)	0.3435 (2)	0.0420 (10)
C7	0.6467 (4)	0.4801 (3)	0.4734 (3)	0.0557 (19)	0.6
H7	0.6831	0.5231	0.4986	0.067*	0.6
C6	0.5407 (4)	0.4930 (3)	0.4496 (3)	0.0505 (18)	0.6
H6	0.5047	0.5447	0.4586	0.061*	0.6
C5	0.4875 (3)	0.4301 (4)	0.4126 (3)	0.042 (2)	0.6
C10	0.5402 (5)	0.3543 (3)	0.3995 (3)	0.056 (2)	0.6
H10	0.5038	0.3113	0.3742	0.067*	0.6
C9	0.6462 (5)	0.3415 (3)	0.4232 (3)	0.066 (2)	0.6
H9	0.6823	0.2897	0.4142	0.079*	0.6
C8	0.6995 (4)	0.4044 (4)	0.4602 (3)	0.056 (3)	0.6
C8A	0.7064 (4)	0.3948 (6)	0.4491 (4)	0.053 (4)	0.4
C7A	0.6784 (5)	0.4640 (5)	0.4099 (4)	0.056 (3)	0.4
H7A	0.7312	0.5053	0.4009	0.067*	0.4
C6A	0.5731 (5)	0.4728 (4)	0.3837 (4)	0.044 (2)	0.4
H6A	0.5539	0.5201	0.3569	0.052*	0.4
C5A	0.4958 (4)	0.4124 (5)	0.3968 (4)	0.025 (2)	0.4
C10A	0.5238 (5)	0.3432 (4)	0.4360 (3)	0.036 (2)	0.4
H10A	0.4709	0.3019	0.4449	0.044*	0.4
C9A	0.6291 (6)	0.3343 (5)	0.4622 (3)	0.045 (3)	0.4
H9A	0.6482	0.2870	0.4890	0.054*	0.4
C11	0.1049 (3)	0.3590 (3)	0.3259 (2)	0.0432 (9)
C12	0.0085 (4)	0.3785 (3)	0.3518 (2)	0.0462 (10)
H12	0.0064	0.4239	0.3816	0.055*
C13	−0.0839 (4)	0.3327 (3)	0.3346 (2)	0.0536 (11)
H13	−0.1491	0.3466	0.3528	0.064*
C14	−0.0824 (4)	0.2669 (4)	0.2912 (2)	0.0597 (13)
C15	0.0134 (5)	0.2452 (4)	0.2664 (3)	0.0627 (14)
H15	0.0142	0.2000	0.2364	0.075*
C16	0.1079 (3)	0.2881 (3)	0.2844 (2)	0.0449 (10)
H16	0.1740	0.2702	0.2691	0.054*
C17	0.3229 (3)	0.6625 (3)	0.36427 (18)	0.0375 (8)
C18	0.3790 (4)	0.7418 (3)	0.3807 (2)	0.0456 (10)
C19	0.3042 (4)	0.8058 (3)	0.3695 (2)	0.0503 (10)
H19	0.3162	0.8654	0.3761	0.060*
C20	0.2055 (3)	0.7669 (3)	0.3463 (2)	0.0417 (9)
C21	0.4929 (3)	0.7426 (4)	0.4094 (3)	0.038 (3)	0.52
C22	0.5461 (4)	0.6775 (3)	0.4441 (3)	0.0442 (18)	0.52
H22	0.5096	0.6254	0.4518	0.053*	0.52
C23	0.6527 (4)	0.6885 (4)	0.4674 (3)	0.052 (2)	0.52
H23	0.6891	0.6439	0.4910	0.063*	0.52
C24	0.7060 (3)	0.7646 (4)	0.4560 (3)	0.045 (3)	0.52
C25	0.6528 (4)	0.8297 (3)	0.4214 (4)	0.061 (3)	0.52
H25	0.6893	0.8818	0.4137	0.073*	0.52
C26	0.5462 (4)	0.8188 (3)	0.3981 (3)	0.054 (2)	0.52
H26	0.5098	0.8633	0.3744	0.065*	0.52
C21A	0.4931 (3)	0.7606 (4)	0.4033 (4)	0.042 (3)	0.48
C22A	0.5685 (4)	0.6954 (4)	0.3994 (3)	0.0433 (19)	0.48
H22A	0.5494	0.6443	0.3768	0.052*	0.48
C23A	0.6718 (4)	0.7051 (4)	0.4284 (3)	0.048 (2)	0.48
H23A	0.7233	0.6606	0.4257	0.058*	0.48
C24A	0.6997 (3)	0.7800 (5)	0.4614 (4)	0.063 (4)	0.48
C25A	0.6243 (5)	0.8452 (4)	0.4653 (4)	0.060 (3)	0.48
H25A	0.6434	0.8964	0.4878	0.072*	0.48
C26A	0.5210 (4)	0.8355 (4)	0.4362 (4)	0.053 (2)	0.48
H26A	0.4695	0.8800	0.4389	0.064*	0.48
C27	0.1061 (4)	0.8147 (3)	0.3295 (2)	0.0495 (10)
C28	0.0087 (4)	0.7942 (3)	0.3542 (3)	0.0588 (13)
H28	0.0063	0.7478	0.3831	0.071*
C29	−0.0839 (4)	0.8396 (4)	0.3376 (3)	0.0736 (17)
H29	−0.1493	0.8248	0.3551	0.088*
C30	−0.0816 (5)	0.9074 (4)	0.2951 (4)	0.084 (2)
C31	0.0150 (5)	0.9302 (4)	0.2714 (4)	0.081 (2)
H31	0.0178	0.9776	0.2434	0.097*
C32	0.1069 (4)	0.8840 (5)	0.2885 (3)	0.0714 (17)
H32	0.1726	0.9001	0.2718	0.086*
C33	0.8669 (5)	0.4488 (6)	0.5063 (4)	0.052 (2)	0.6
H33A	0.8732	0.4918	0.4730	0.078*	0.6
H33B	0.9386	0.4277	0.5209	0.078*	0.6
H33C	0.8331	0.4749	0.5418	0.078*	0.6
C33A	0.8538 (19)	0.3436 (13)	0.5043 (9)	0.119 (8)	0.4
H33D	0.8403	0.2878	0.4839	0.179*	0.4
H33E	0.8162	0.3464	0.5432	0.179*	0.4
H33F	0.9314	0.3508	0.5147	0.179*	0.4
C34A	−0.2593 (9)	0.2262 (10)	0.2969 (8)	0.090 (4)	0.5
H34A	−0.2535	0.2187	0.3429	0.134*	0.5
H34B	−0.3161	0.1887	0.2778	0.134*	0.5
H34C	−0.2771	0.2861	0.2865	0.134*	0.5
C34	−0.1964 (8)	0.1730 (6)	0.2259 (5)	0.060 (3)	0.5
H34D	−0.1591	0.1206	0.2409	0.090*	0.5
H34E	−0.1641	0.1944	0.1883	0.090*	0.5
H34F	−0.2727	0.1603	0.2153	0.090*	0.5
C35	0.8706 (4)	0.7169 (5)	0.5035 (3)	0.0769 (19)
H35A	0.8329	0.6822	0.5333	0.115*
H35B	0.9388	0.7375	0.5243	0.115*
H35C	0.8851	0.6818	0.4667	0.115*
C36	−0.1918 (8)	1.0012 (7)	0.2223 (5)	0.070 (3)	0.52
H36A	−0.2704	1.0042	0.2153	0.106*	0.52
H36B	−0.1638	0.9615	0.1917	0.106*	0.52
H36C	−0.1611	1.0584	0.2168	0.106*	0.52
C36A	−0.2596 (9)	0.9531 (9)	0.3164 (7)	0.090 (5)	0.48
H36D	−0.3000	1.0052	0.3041	0.135*	0.48
H36E	−0.2200	0.9619	0.3577	0.135*	0.48
H36F	−0.3097	0.9050	0.3190	0.135*	0.48
C37	0.0374 (4)	0.5037 (4)	0.2360 (2)	0.0613 (14)
C38	−0.0016 (4)	0.5870 (3)	0.3416 (2)	0.0536 (12)
C39	0.0381 (4)	0.6718 (4)	0.2366 (2)	0.0543 (12)
C40	0.2954 (4)	0.5899 (3)	0.1837 (2)	0.0462 (10)
C41	0.3622 (5)	0.5914 (5)	0.1302 (3)	0.086 (2)
H41A	0.3588	0.5354	0.1092	0.129*
H41B	0.4369	0.6040	0.1453	0.129*
H41C	0.3357	0.6358	0.1001	0.129*
C42	−0.1484 (18)	1.1450 (10)	0.4621 (14)	0.328 (14)
H42A	−0.0904	1.1788	0.4457	0.492*
H42B	−0.1563	1.1610	0.5062	0.492*
H42C	−0.2160	1.1562	0.4366	0.492*
C43	−0.1210 (10)	1.0495 (9)	0.4586 (7)	0.199 (7)
H43A	−0.1079	1.0323	0.4149	0.239*
H43B	−0.1793	1.0136	0.4738	0.239*
C44	−0.0181 (9)	1.0428 (7)	0.5028 (6)	0.159 (6)
H44A	0.0369	1.0838	0.4900	0.191*
H44B	−0.0333	1.0553	0.5471	0.191*
N5	0.6344 (11)	0.9652 (13)	0.5650 (10)	0.096 (5)	0.54
C45	0.5566 (11)	0.9235 (8)	0.5570 (7)	0.073 (3)	0.54
C46	0.4575 (11)	0.8778 (10)	0.5485 (6)	0.095 (4)	0.54
H46D	0.4602	0.8378	0.5130	0.143*	0.54
H46E	0.3982	0.9184	0.5396	0.143*	0.54
H46F	0.4460	0.8456	0.5871	0.143*	0.54
N5A	0.6062 (13)	0.9826 (16)	0.5855 (12)	0.096 (5)	0.46
C45A	0.5203 (11)	0.9522 (9)	0.5829 (7)	0.067 (3)	0.46
C46A	0.4157 (11)	0.9149 (9)	0.5814 (7)	0.076 (4)	0.46
H46A	0.3733	0.9331	0.5428	0.115*	0.46
H46B	0.3798	0.9339	0.6185	0.115*	0.46
H46C	0.4220	0.8522	0.5818	0.115*	0.46

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Re1	0.02553 (11)	0.04698 (13)	0.03484 (12)	−0.00191 (6)	−0.00143 (7)	0.00835 (7)
O1	0.034 (3)	0.070 (5)	0.062 (5)	0.029 (3)	−0.017 (3)	0.009 (4)
O1A	0.068 (8)	0.107 (12)	0.079 (10)	0.040 (7)	−0.001 (6)	0.021 (7)
O2A	0.063 (5)	0.072 (8)	0.102 (7)	−0.025 (5)	0.015 (6)	−0.034 (7)
O2	0.049 (5)	0.051 (5)	0.064 (5)	−0.023 (4)	0.000 (4)	−0.009 (5)
O3	0.051 (2)	0.098 (3)	0.121 (4)	−0.037 (2)	−0.024 (2)	0.017 (3)
O4	0.074 (6)	0.067 (7)	0.108 (8)	0.042 (5)	0.034 (5)	0.031 (6)
O4A	0.065 (6)	0.045 (5)	0.093 (7)	0.027 (4)	0.016 (5)	0.000 (5)
O5	0.137 (4)	0.111 (4)	0.066 (3)	−0.081 (4)	−0.055 (3)	0.032 (3)
O6	0.0289 (17)	0.106 (3)	0.058 (2)	−0.0010 (16)	0.0128 (15)	0.0168 (18)
O7	0.105 (3)	0.123 (4)	0.049 (2)	0.071 (3)	−0.005 (2)	0.020 (2)
N1	0.0272 (16)	0.0443 (18)	0.0437 (18)	−0.0032 (14)	−0.0034 (13)	0.0156 (15)
N2	0.0287 (17)	0.050 (2)	0.0364 (18)	−0.0021 (13)	−0.0001 (14)	0.0091 (14)
N3	0.0287 (16)	0.0432 (18)	0.0381 (17)	0.0009 (13)	0.0020 (13)	−0.0007 (14)
N4	0.0355 (18)	0.0321 (16)	0.0404 (18)	−0.0003 (12)	0.0040 (15)	−0.0004 (13)
C1	0.0276 (19)	0.049 (2)	0.049 (2)	−0.0045 (17)	−0.0056 (16)	0.0194 (19)
C2	0.037 (2)	0.051 (2)	0.058 (3)	−0.0007 (19)	−0.0038 (19)	0.023 (2)
C3	0.038 (2)	0.046 (2)	0.056 (3)	−0.0035 (18)	0.0005 (19)	0.017 (2)
C4	0.037 (2)	0.051 (2)	0.038 (2)	−0.0066 (17)	0.0035 (17)	0.0077 (17)
C7	0.049 (4)	0.065 (5)	0.053 (4)	0.013 (4)	0.001 (3)	0.002 (4)
C6	0.049 (4)	0.057 (4)	0.045 (4)	0.015 (4)	0.002 (3)	0.002 (3)
C5	0.047 (5)	0.037 (4)	0.043 (5)	0.010 (3)	0.007 (4)	0.002 (4)
C10	0.047 (4)	0.040 (4)	0.080 (6)	0.010 (4)	0.006 (4)	−0.001 (4)
C9	0.052 (5)	0.055 (5)	0.091 (7)	0.025 (4)	0.013 (5)	0.009 (5)
C8	0.047 (6)	0.071 (6)	0.050 (5)	0.026 (5)	0.000 (4)	0.006 (5)
C8A	0.030 (7)	0.066 (8)	0.060 (8)	0.022 (6)	−0.006 (6)	−0.025 (7)
C7A	0.017 (4)	0.057 (7)	0.093 (9)	0.002 (4)	−0.002 (5)	−0.016 (6)
C6A	0.025 (4)	0.043 (5)	0.062 (6)	0.005 (4)	0.000 (4)	−0.004 (5)
C5A	0.022 (5)	0.031 (6)	0.022 (5)	0.003 (4)	−0.002 (4)	−0.010 (4)
C10A	0.037 (5)	0.050 (6)	0.023 (4)	0.018 (4)	0.002 (4)	−0.003 (4)
C9A	0.043 (6)	0.062 (7)	0.029 (5)	0.028 (5)	−0.003 (4)	−0.010 (5)
C11	0.041 (2)	0.050 (2)	0.039 (2)	−0.0106 (18)	0.0047 (17)	0.0074 (18)
C12	0.045 (2)	0.054 (3)	0.040 (2)	−0.009 (2)	0.0037 (18)	0.0052 (19)
C13	0.040 (2)	0.069 (3)	0.053 (3)	−0.013 (2)	0.009 (2)	0.002 (2)
C14	0.056 (3)	0.070 (3)	0.054 (3)	−0.025 (2)	0.007 (2)	−0.003 (2)
C15	0.071 (3)	0.062 (3)	0.057 (3)	−0.027 (3)	0.019 (3)	−0.012 (2)
C16	0.046 (2)	0.040 (2)	0.049 (2)	−0.0141 (18)	0.0083 (19)	−0.0024 (18)
C17	0.0274 (18)	0.050 (2)	0.0353 (19)	−0.0001 (16)	0.0006 (15)	−0.0021 (17)
C18	0.040 (2)	0.055 (3)	0.042 (2)	−0.0022 (19)	0.0017 (17)	−0.0076 (19)
C19	0.046 (2)	0.048 (2)	0.057 (3)	−0.003 (2)	0.008 (2)	−0.008 (2)
C20	0.039 (2)	0.044 (2)	0.043 (2)	0.0028 (17)	0.0092 (17)	−0.0004 (17)
C21	0.049 (6)	0.031 (4)	0.036 (5)	−0.016 (4)	0.011 (4)	−0.008 (4)
C22	0.050 (5)	0.046 (4)	0.035 (4)	−0.019 (4)	−0.002 (3)	0.006 (3)
C23	0.053 (5)	0.067 (6)	0.036 (4)	−0.023 (4)	−0.006 (4)	0.002 (4)
C24	0.037 (6)	0.057 (6)	0.042 (6)	−0.006 (5)	0.007 (5)	−0.004 (5)
C25	0.057 (6)	0.039 (5)	0.088 (7)	−0.023 (4)	0.020 (5)	−0.013 (5)
C26	0.050 (5)	0.028 (4)	0.086 (7)	−0.010 (4)	0.014 (5)	0.002 (4)
C21A	0.038 (6)	0.042 (6)	0.044 (6)	0.003 (4)	−0.009 (5)	0.011 (5)
C22A	0.037 (4)	0.046 (5)	0.046 (5)	−0.009 (4)	−0.003 (4)	−0.003 (4)
C23A	0.036 (4)	0.059 (6)	0.047 (5)	−0.008 (4)	−0.008 (4)	0.000 (5)
C24A	0.047 (8)	0.070 (8)	0.068 (9)	−0.030 (6)	−0.011 (7)	0.006 (7)
C25A	0.060 (6)	0.047 (5)	0.072 (7)	−0.018 (5)	−0.012 (5)	−0.014 (5)
C26A	0.053 (6)	0.036 (5)	0.070 (6)	−0.012 (4)	0.002 (5)	−0.006 (5)
C27	0.042 (2)	0.050 (2)	0.059 (3)	0.0089 (19)	0.014 (2)	0.004 (2)
C28	0.053 (3)	0.058 (3)	0.068 (3)	0.011 (2)	0.025 (2)	0.013 (2)
C29	0.044 (3)	0.074 (4)	0.106 (5)	0.016 (3)	0.033 (3)	0.025 (3)
C30	0.057 (3)	0.078 (4)	0.121 (6)	0.032 (3)	0.039 (4)	0.040 (4)
C31	0.063 (4)	0.067 (3)	0.119 (5)	0.026 (3)	0.041 (4)	0.043 (4)
C32	0.048 (3)	0.097 (4)	0.074 (4)	0.016 (3)	0.031 (3)	0.020 (3)
C33	0.024 (3)	0.092 (6)	0.039 (4)	0.013 (4)	−0.007 (3)	0.014 (4)
C33A	0.093 (15)	0.19 (2)	0.075 (12)	−0.013 (16)	0.012 (11)	0.003 (14)
C34A	0.048 (7)	0.104 (11)	0.117 (11)	−0.016 (7)	0.009 (7)	−0.020 (9)
C34	0.050 (5)	0.052 (5)	0.075 (7)	−0.015 (4)	−0.013 (5)	−0.007 (5)
C35	0.047 (3)	0.125 (6)	0.056 (3)	−0.028 (3)	−0.012 (2)	0.014 (3)
C36	0.046 (5)	0.058 (6)	0.103 (9)	0.017 (5)	−0.019 (5)	−0.001 (6)
C36A	0.041 (6)	0.077 (9)	0.152 (14)	0.004 (6)	0.008 (7)	0.009 (9)
C37	0.052 (3)	0.082 (4)	0.048 (3)	−0.021 (3)	−0.012 (2)	0.028 (3)
C38	0.039 (3)	0.072 (3)	0.048 (3)	−0.001 (2)	−0.010 (2)	0.014 (2)
C39	0.043 (2)	0.077 (3)	0.043 (2)	0.013 (2)	0.0062 (19)	0.006 (2)
C40	0.041 (2)	0.054 (3)	0.044 (2)	−0.0004 (18)	0.004 (2)	−0.0074 (18)
C41	0.063 (4)	0.145 (7)	0.053 (3)	−0.009 (4)	0.024 (3)	−0.018 (3)
C42	0.21 (2)	0.31 (3)	0.46 (4)	−0.01 (2)	0.00 (2)	−0.03 (3)
C43	0.142 (11)	0.264 (18)	0.196 (14)	−0.062 (13)	0.029 (10)	−0.016 (14)
C44	0.165 (10)	0.192 (12)	0.127 (8)	−0.101 (12)	0.057 (7)	−0.009 (10)
N5	0.107 (9)	0.087 (9)	0.091 (13)	−0.004 (8)	−0.011 (7)	0.005 (7)
C45	0.096 (10)	0.064 (7)	0.057 (7)	0.002 (6)	−0.004 (7)	−0.006 (5)
C46	0.115 (11)	0.110 (11)	0.059 (7)	−0.026 (9)	−0.002 (7)	0.017 (7)
N5A	0.107 (9)	0.087 (9)	0.091 (13)	−0.004 (8)	−0.011 (7)	0.005 (7)
C45A	0.091 (10)	0.057 (8)	0.051 (7)	−0.013 (7)	−0.012 (7)	0.002 (6)
C46A	0.104 (12)	0.076 (9)	0.048 (7)	−0.008 (7)	0.000 (7)	−0.008 (6)

Geometric parameters (Å, º)

Re1—N1	2.185 (3)	C21—C22	1.3900
Re1—N3	2.190 (3)	C21—C26	1.3900
Re1—N4	2.181 (4)	C22—H22	0.9500
Re1—C37	1.925 (6)	C22—C23	1.3900
Re1—C38	1.901 (6)	C23—H23	0.9500
Re1—C39	1.923 (5)	C23—C24	1.3900
O1—C8	1.396 (6)	C24—C25	1.3900
O1—C33	1.390 (12)	C25—H25	0.9500
O1A—C8A	1.396 (6)	C25—C26	1.3900
O1A—C33A	1.390 (12)	C26—H26	0.9500
O2A—C14	1.396 (6)	C21A—C22A	1.3900
O2A—C34A	1.431 (11)	C21A—C26A	1.3900
O2—C14	1.397 (6)	C22A—H22A	0.9500
O2—C34	1.431 (11)	C22A—C23A	1.3900
O3—C24	1.388 (5)	C23A—H23A	0.9500
O3—C24A	1.387 (5)	C23A—C24A	1.3900
O3—C35	1.386 (8)	C24A—C25A	1.3900
O4—C30	1.409 (7)	C25A—H25A	0.9500
O4—C36	1.457 (13)	C25A—C26A	1.3900
O4A—C30	1.410 (7)	C26A—H26A	0.9500
O4A—C36A	1.456 (13)	C27—C28	1.396 (6)
O5—C37	1.152 (7)	C27—C32	1.387 (8)
O6—C38	1.160 (6)	C28—H28	0.9500
O7—C39	1.147 (6)	C28—C29	1.375 (7)
N1—C1	1.403 (5)	C29—H29	0.9500
N1—C4	1.345 (5)	C29—C30	1.390 (8)
N2—C1	1.319 (5)	C30—C31	1.385 (8)
N2—C17	1.312 (5)	C31—H31	0.9500
N3—C17	1.406 (5)	C31—C32	1.376 (8)
N3—C20	1.348 (5)	C32—H32	0.9500
N4—C40	1.120 (6)	C33—H33A	0.9800
C1—C2	1.440 (6)	C33—H33B	0.9800
C2—C3	1.377 (7)	C33—H33C	0.9800
C2—C5	1.490 (6)	C33A—H33D	0.9800
C2—C5A	1.513 (6)	C33A—H33E	0.9800
C3—H3	0.9500	C33A—H33F	0.9800
C3—C4	1.419 (6)	C34A—H34A	0.9800
C4—C11	1.477 (6)	C34A—H34B	0.9800
C7—H7	0.9500	C34A—H34C	0.9800
C7—C6	1.3900	C34—H34D	0.9800
C7—C8	1.3900	C34—H34E	0.9800
C6—H6	0.9500	C34—H34F	0.9800
C6—C5	1.3900	C35—H35A	0.9800
C5—C10	1.3900	C35—H35B	0.9800
C10—H10	0.9500	C35—H35C	0.9800
C10—C9	1.3900	C36—H36A	0.9800
C9—H9	0.9500	C36—H36B	0.9800
C9—C8	1.3900	C36—H36C	0.9800
C8A—C7A	1.3900	C36A—H36D	0.9800
C8A—C9A	1.3900	C36A—H36E	0.9800
C7A—H7A	0.9500	C36A—H36F	0.9800
C7A—C6A	1.3900	C40—C41	1.458 (7)
C6A—H6A	0.9500	C41—H41A	0.9800
C6A—C5A	1.3900	C41—H41B	0.9800
C5A—C10A	1.3900	C41—H41C	0.9800
C10A—H10A	0.9500	C42—H42A	0.9800
C10A—C9A	1.3900	C42—H42B	0.9800
C9A—H9A	0.9500	C42—H42C	0.9800
C11—C12	1.393 (6)	C42—C43	1.5287 (10)
C11—C16	1.413 (6)	C43—H43A	0.9900
C12—H12	0.9500	C43—H43B	0.9900
C12—C13	1.379 (6)	C43—C44	1.5307 (11)
C13—H13	0.9500	C44—C44^i	1.42 (2)
C13—C14	1.379 (7)	C44—H44A	0.9900
C14—C15	1.384 (8)	C44—H44B	0.9900
C15—H15	0.9500	N5—C45	1.168 (11)
C15—C16	1.380 (7)	C45—C46	1.424 (13)
C16—H16	0.9500	C46—H46D	0.9800
C17—C18	1.448 (6)	C46—H46E	0.9800
C18—C19	1.372 (7)	C46—H46F	0.9800
C18—C21	1.499 (5)	N5A—C45A	1.168 (11)
C18—C21A	1.492 (5)	C45A—C46A	1.424 (13)
C19—H19	0.9500	C46A—H46A	0.9800
C19—C20	1.423 (6)	C46A—H46B	0.9800
C20—C27	1.463 (6)	C46A—H46C	0.9800
N1—Re1—N3	84.34 (14)	C26—C25—C24	120.0
N4—Re1—N1	84.63 (13)	C26—C25—H25	120.0
N4—Re1—N3	84.67 (12)	C21—C26—H26	120.0
C37—Re1—N1	94.51 (19)	C25—C26—C21	120.0
C37—Re1—N3	174.45 (19)	C25—C26—H26	120.0
C37—Re1—N4	89.82 (19)	C22A—C21A—C18	117.9 (4)
C38—Re1—N1	97.65 (16)	C22A—C21A—C26A	120.0
C38—Re1—N3	97.26 (18)	C26A—C21A—C18	121.3 (4)
C38—Re1—N4	177.14 (16)	C21A—C22A—H22A	120.0
C38—Re1—C37	88.3 (2)	C23A—C22A—C21A	120.0
C38—Re1—C39	88.5 (2)	C23A—C22A—H22A	120.0
C39—Re1—N1	173.87 (16)	C22A—C23A—H23A	120.0
C39—Re1—N3	94.8 (2)	C24A—C23A—C22A	120.0
C39—Re1—N4	89.26 (16)	C24A—C23A—H23A	120.0
C39—Re1—C37	85.8 (2)	O3—C24A—C23A	115.4 (5)
C33—O1—C8	114.0 (7)	O3—C24A—C25A	124.4 (5)
C33A—O1A—C8A	107.3 (14)	C23A—C24A—C25A	120.0
C14—O2A—C34A	109.2 (9)	C24A—C25A—H25A	120.0
C14—O2—C34	116.2 (8)	C24A—C25A—C26A	120.0
C35—O3—C24	114.5 (5)	C26A—C25A—H25A	120.0
C35—O3—C24A	124.1 (5)	C21A—C26A—H26A	120.0
C30—O4—C36	118.5 (9)	C25A—C26A—C21A	120.0
C30—O4A—C36A	114.1 (10)	C25A—C26A—H26A	120.0
C1—N1—Re1	121.7 (3)	C28—C27—C20	122.4 (4)
C4—N1—Re1	129.6 (3)	C32—C27—C20	120.1 (4)
C4—N1—C1	106.2 (3)	C32—C27—C28	117.5 (4)
C17—N2—C1	128.3 (4)	C27—C28—H28	119.2
C17—N3—Re1	121.6 (3)	C29—C28—C27	121.5 (5)
C20—N3—Re1	129.7 (3)	C29—C28—H28	119.2
C20—N3—C17	106.1 (3)	C28—C29—H29	120.1
C40—N4—Re1	169.3 (4)	C28—C29—C30	119.8 (5)
N1—C1—C2	109.4 (4)	C30—C29—H29	120.1
N2—C1—N1	127.6 (4)	C29—C30—O4	124.6 (7)
N2—C1—C2	123.0 (4)	C29—C30—O4A	114.3 (7)
C1—C2—C5	122.0 (4)	C31—C30—O4	113.6 (7)
C1—C2—C5A	131.9 (5)	C31—C30—O4A	124.6 (8)
C3—C2—C1	105.7 (4)	C31—C30—C29	119.5 (5)
C3—C2—C5	131.3 (4)	C30—C31—H31	120.0
C3—C2—C5A	122.1 (5)	C32—C31—C30	119.9 (5)
C2—C3—H3	126.2	C32—C31—H31	120.0
C2—C3—C4	107.7 (4)	C27—C32—H32	119.1
C4—C3—H3	126.2	C31—C32—C27	121.7 (5)
N1—C4—C3	111.0 (4)	C31—C32—H32	119.1
N1—C4—C11	125.1 (4)	O1—C33—H33A	109.5
C3—C4—C11	123.9 (4)	O1—C33—H33B	109.5
C6—C7—H7	120.0	O1—C33—H33C	109.5
C6—C7—C8	120.0	H33A—C33—H33B	109.5
C8—C7—H7	120.0	H33A—C33—H33C	109.5
C7—C6—H6	120.0	H33B—C33—H33C	109.5
C5—C6—C7	120.0	O1A—C33A—H33D	109.5
C5—C6—H6	120.0	O1A—C33A—H33E	109.5
C6—C5—C2	129.8 (4)	O1A—C33A—H33F	109.5
C6—C5—C10	120.0	H33D—C33A—H33E	109.5
C10—C5—C2	110.0 (4)	H33D—C33A—H33F	109.5
C5—C10—H10	120.0	H33E—C33A—H33F	109.5
C9—C10—C5	120.0	O2A—C34A—H34A	109.5
C9—C10—H10	120.0	O2A—C34A—H34B	109.5
C10—C9—H9	120.0	O2A—C34A—H34C	109.5
C10—C9—C8	120.0	H34A—C34A—H34B	109.5
C8—C9—H9	120.0	H34A—C34A—H34C	109.5
C7—C8—O1	126.7 (6)	H34B—C34A—H34C	109.5
C9—C8—O1	113.2 (6)	O2—C34—H34D	109.5
C9—C8—C7	120.0	O2—C34—H34E	109.5
C7A—C8A—O1A	101.8 (8)	O2—C34—H34F	109.5
C7A—C8A—C9A	120.0	H34D—C34—H34E	109.5
C9A—C8A—O1A	138.1 (8)	H34D—C34—H34F	109.5
C8A—C7A—H7A	120.0	H34E—C34—H34F	109.5
C8A—C7A—C6A	120.0	O3—C35—H35A	109.5
C6A—C7A—H7A	120.0	O3—C35—H35B	109.5
C7A—C6A—H6A	120.0	O3—C35—H35C	109.5
C5A—C6A—C7A	120.0	H35A—C35—H35B	109.5
C5A—C6A—H6A	120.0	H35A—C35—H35C	109.5
C6A—C5A—C2	119.0 (4)	H35B—C35—H35C	109.5
C6A—C5A—C10A	120.0	O4—C36—H36A	109.5
C10A—C5A—C2	120.0 (4)	O4—C36—H36B	109.5
C5A—C10A—H10A	120.0	O4—C36—H36C	109.5
C9A—C10A—C5A	120.0	H36A—C36—H36B	109.5
C9A—C10A—H10A	120.0	H36A—C36—H36C	109.5
C8A—C9A—H9A	120.0	H36B—C36—H36C	109.5
C10A—C9A—C8A	120.0	O4A—C36A—H36D	109.5
C10A—C9A—H9A	120.0	O4A—C36A—H36E	109.5
C12—C11—C4	121.9 (4)	O4A—C36A—H36F	109.5
C12—C11—C16	118.8 (4)	H36D—C36A—H36E	109.5
C16—C11—C4	119.2 (4)	H36D—C36A—H36F	109.5
C11—C12—H12	119.7	H36E—C36A—H36F	109.5
C13—C12—C11	120.7 (5)	O5—C37—Re1	175.4 (5)
C13—C12—H12	119.7	O6—C38—Re1	176.8 (4)
C12—C13—H13	119.8	O7—C39—Re1	173.8 (5)
C14—C13—C12	120.4 (5)	N4—C40—C41	178.6 (6)
C14—C13—H13	119.8	C40—C41—H41A	109.5
C13—C14—O2A	131.4 (7)	C40—C41—H41B	109.5
C13—C14—O2	110.9 (6)	C40—C41—H41C	109.5
C13—C14—C15	119.5 (5)	H41A—C41—H41B	109.5
C15—C14—O2A	108.2 (6)	H41A—C41—H41C	109.5
C15—C14—O2	129.2 (6)	H41B—C41—H41C	109.5
C14—C15—H15	119.4	H42A—C42—H42B	109.5
C16—C15—C14	121.2 (5)	H42A—C42—H42C	109.5
C16—C15—H15	119.4	H42B—C42—H42C	109.5
C11—C16—H16	120.4	C43—C42—H42A	109.5
C15—C16—C11	119.2 (4)	C43—C42—H42B	109.5
C15—C16—H16	120.4	C43—C42—H42C	109.5
N2—C17—N3	127.4 (4)	C42—C43—H43A	111.3
N2—C17—C18	123.2 (4)	C42—C43—H43B	111.3
N3—C17—C18	109.4 (4)	C42—C43—C44	102.5 (13)
C17—C18—C21	121.9 (4)	H43A—C43—H43B	109.2
C17—C18—C21A	132.4 (4)	C44—C43—H43A	111.3
C19—C18—C17	105.6 (4)	C44—C43—H43B	111.3
C19—C18—C21	132.2 (5)	C43—C44—H44A	110.6
C19—C18—C21A	121.9 (5)	C43—C44—H44B	110.6
C18—C19—H19	126.1	C44^i—C44—C43	105.6 (13)
C18—C19—C20	107.9 (4)	C44^i—C44—H44A	110.6
C20—C19—H19	126.1	C44^i—C44—H44B	110.6
N3—C20—C19	111.0 (4)	H44A—C44—H44B	108.8
N3—C20—C27	125.0 (4)	N5—C45—C46	176.0 (18)
C19—C20—C27	124.0 (4)	C45—C46—H46D	109.5
C22—C21—C18	127.2 (4)	C45—C46—H46E	109.5
C22—C21—C26	120.0	C45—C46—H46F	109.5
C26—C21—C18	112.8 (4)	H46D—C46—H46E	109.5
C21—C22—H22	120.0	H46D—C46—H46F	109.5
C21—C22—C23	120.0	H46E—C46—H46F	109.5
C23—C22—H22	120.0	N5A—C45A—C46A	179 (2)
C22—C23—H23	120.0	C45A—C46A—H46A	109.5
C22—C23—C24	120.0	C45A—C46A—H46B	109.5
C24—C23—H23	120.0	C45A—C46A—H46C	109.5
O3—C24—C23	124.4 (5)	H46A—C46A—H46B	109.5
O3—C24—C25	115.1 (5)	H46A—C46A—H46C	109.5
C25—C24—C23	120.0	H46B—C46A—H46C	109.5
C24—C25—H25	120.0
Re1—N1—C1—N2	19.0 (6)	C12—C11—C16—C15	5.8 (7)
Re1—N1—C1—C2	−162.9 (3)	C12—C13—C14—O2A	170.2 (10)
Re1—N1—C4—C3	161.1 (3)	C12—C13—C14—O2	−172.3 (7)
Re1—N1—C4—C11	−19.3 (6)	C12—C13—C14—C15	2.0 (8)
Re1—N3—C17—N2	−19.3 (6)	C13—C14—C15—C16	0.2 (9)
Re1—N3—C17—C18	162.7 (3)	C14—C15—C16—C11	−4.1 (8)
Re1—N3—C20—C19	−161.2 (3)	C16—C11—C12—C13	−3.6 (7)
Re1—N3—C20—C27	19.7 (6)	C17—N2—C1—N1	4.4 (8)
O1A—C8A—C7A—C6A	178.6 (11)	C17—N2—C1—C2	−173.4 (4)
O1A—C8A—C9A—C10A	−177.9 (17)	C17—N3—C20—C19	0.3 (5)
O2A—C14—C15—C16	−170.4 (9)	C17—N3—C20—C27	−178.9 (4)
O2—C14—C15—C16	173.4 (8)	C17—C18—C19—C20	−0.6 (5)
O3—C24—C25—C26	−172.0 (7)	C17—C18—C21—C22	−24.6 (7)
O3—C24A—C25A—C26A	174.1 (8)	C17—C18—C21—C26	155.1 (4)
O4—C30—C31—C32	165.7 (9)	C17—C18—C21A—C22A	12.5 (9)
O4A—C30—C31—C32	−162.8 (8)	C17—C18—C21A—C26A	−157.6 (5)
N1—C1—C2—C3	−0.5 (5)	C18—C19—C20—N3	0.2 (5)
N1—C1—C2—C5	−169.7 (5)	C18—C19—C20—C27	179.4 (4)
N1—C1—C2—C5A	172.4 (6)	C18—C21—C22—C23	179.7 (7)
N1—C4—C11—C12	−53.1 (6)	C18—C21—C26—C25	−179.8 (6)
N1—C4—C11—C16	130.7 (5)	C18—C21A—C22A—C23A	−170.2 (7)
N2—C1—C2—C3	177.7 (4)	C18—C21A—C26A—C25A	169.8 (8)
N2—C1—C2—C5	8.4 (8)	C19—C18—C21—C22	148.8 (5)
N2—C1—C2—C5A	−9.4 (9)	C19—C18—C21—C26	−31.5 (7)
N2—C17—C18—C19	−177.3 (4)	C19—C18—C21A—C22A	−165.3 (4)
N2—C17—C18—C21	−2.4 (7)	C19—C18—C21A—C26A	24.7 (8)
N2—C17—C18—C21A	4.6 (8)	C19—C20—C27—C28	−127.0 (6)
N3—C17—C18—C19	0.8 (5)	C19—C20—C27—C32	51.9 (7)
N3—C17—C18—C21	175.7 (4)	C20—N3—C17—N2	177.4 (4)
N3—C17—C18—C21A	−177.2 (6)	C20—N3—C17—C18	−0.7 (4)
N3—C20—C27—C28	52.1 (7)	C20—C27—C28—C29	−179.7 (6)
N3—C20—C27—C32	−129.0 (6)	C20—C27—C32—C31	179.6 (6)
C1—N1—C4—C3	−0.8 (5)	C21—C18—C19—C20	−174.8 (5)
C1—N1—C4—C11	178.8 (4)	C21—C22—C23—C24	0.0
C1—N2—C17—N3	−4.2 (7)	C22—C21—C26—C25	0.0
C1—N2—C17—C18	173.6 (4)	C22—C23—C24—O3	171.2 (7)
C1—C2—C3—C4	0.0 (5)	C22—C23—C24—C25	0.0
C1—C2—C5—C6	19.3 (8)	C23—C24—C25—C26	0.0
C1—C2—C5—C10	−156.0 (4)	C24—C25—C26—C21	0.0
C1—C2—C5A—C6A	−18.3 (9)	C26—C21—C22—C23	0.0
C1—C2—C5A—C10A	150.2 (5)	C21A—C18—C19—C20	177.7 (5)
C2—C3—C4—N1	0.5 (6)	C21A—C22A—C23A—C24A	0.0
C2—C3—C4—C11	−179.1 (4)	C22A—C21A—C26A—C25A	0.0
C2—C5—C10—C9	175.9 (5)	C22A—C23A—C24A—O3	−174.7 (8)
C2—C5A—C10A—C9A	−168.4 (7)	C22A—C23A—C24A—C25A	0.0
C3—C2—C5—C6	−146.8 (5)	C23A—C24A—C25A—C26A	0.0
C3—C2—C5—C10	37.8 (7)	C24A—C25A—C26A—C21A	0.0
C3—C2—C5A—C6A	153.6 (5)	C26A—C21A—C22A—C23A	0.0
C3—C2—C5A—C10A	−37.9 (8)	C27—C28—C29—C30	0.4 (10)
C3—C4—C11—C12	126.4 (5)	C28—C27—C32—C31	−1.4 (10)
C3—C4—C11—C16	−49.8 (6)	C28—C29—C30—O4	−163.8 (9)
C4—N1—C1—N2	−177.3 (4)	C28—C29—C30—O4A	164.3 (7)
C4—N1—C1—C2	0.8 (5)	C28—C29—C30—C31	−2.1 (12)
C4—C11—C12—C13	−179.8 (4)	C29—C30—C31—C32	2.1 (13)
C4—C11—C16—C15	−177.9 (4)	C30—C31—C32—C27	−0.3 (12)
C7—C6—C5—C2	−174.9 (7)	C32—C27—C28—C29	1.4 (9)
C7—C6—C5—C10	0.0	C33—O1—C8—C7	−16.6 (12)
C6—C7—C8—O1	−177.6 (8)	C33—O1—C8—C9	165.6 (7)
C6—C7—C8—C9	0.0	C33A—O1A—C8A—C7A	178.5 (15)
C6—C5—C10—C9	0.0	C33A—O1A—C8A—C9A	−3 (3)
C5—C2—C3—C4	167.8 (5)	C34A—O2A—C14—C13	11.7 (19)
C5—C10—C9—C8	0.0	C34A—O2A—C14—C15	−179.1 (11)
C10—C9—C8—O1	177.9 (7)	C34—O2—C14—C13	175.1 (8)
C10—C9—C8—C7	0.0	C34—O2—C14—C15	1.5 (15)
C8—C7—C6—C5	0.0	C35—O3—C24—C23	24.7 (8)
C8A—C7A—C6A—C5A	0.0	C35—O3—C24—C25	−163.6 (5)
C7A—C8A—C9A—C10A	0.0	C35—O3—C24A—C23A	−32.6 (9)
C7A—C6A—C5A—C2	168.5 (7)	C35—O3—C24A—C25A	153.0 (6)
C7A—C6A—C5A—C10A	0.0	C36—O4—C30—C29	−141.1 (10)
C6A—C5A—C10A—C9A	0.0	C36—O4—C30—C31	56.2 (14)
C5A—C2—C3—C4	−173.7 (5)	C36A—O4A—C30—C29	52.5 (12)
C5A—C10A—C9A—C8A	0.0	C36A—O4A—C30—C31	−141.9 (11)
C9A—C8A—C7A—C6A	0.0	C42—C43—C44—C44^i	−174.4 (15)
C11—C12—C13—C14	−0.3 (7)

Symmetry code: (i) −x, −y+2, −z+1.

(3) fac-(2-{[3,5-Bis(4-methoxyphenyl)-2H-pyrrol-2-ylidene-κN¹]amino}-3,5-bis(4-methoxyphenyl)-1H-pyrrol-1-ido-κN¹)tricarbonyl(dimethyl sulfoxide-κO)rhenium(I),

Crystal data

[Re(C36H30N3O4)(C2H6OS)(CO)3]	Z = 2
Mr = 916.99	F(000) = 916
Triclinic, P1	Dx = 1.648 Mg m^−3
a = 10.7054 (4) Å	Cu Kα radiation, λ = 1.54178 Å
b = 10.9330 (4) Å	Cell parameters from 9592 reflections
c = 16.7416 (7) Å	θ = 5.3–69.3°
α = 78.195 (2)°	µ = 7.45 mm^−1
β = 81.029 (2)°	T = 150 K
γ = 75.883 (2)°	Block, black
V = 1848.46 (13) Å^3	0.21 × 0.13 × 0.07 mm

Data collection

Bruker Microstar diffractometer	6882 independent reflections
Radiation source: Rotating Anode	6811 reflections with I > 2σ(I)
Detector resolution: 8.3 pixels mm^-1	Rint = 0.042
ω scans	θmax = 69.7°, θmin = 4.2°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −13→13
Tmin = 0.490, Tmax = 0.753	k = −13→13
74487 measured reflections	l = −20→14

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.032	H-atom parameters constrained
wR(F^2) = 0.089	w = 1/[σ^2(Fo^2) + (0.0545P)^2 + 3.5218P] where P = (Fo^2 + 2Fc^2)/3
S = 1.12	(Δ/σ)max < 0.001
6882 reflections	Δρmax = 1.60 e Å^−3
493 parameters	Δρmin = −0.77 e Å^−3
0 restraints

Special details

Experimental. Crystallographic data for the title compound were collected at 150 K, from single-crystal samples, which were mounted on a loop fiber. Data were collected using a Bruker Microstar diffractometer equipped with a Platinum 135 CCD Detector, a Helios optics and a Kappa goniometer. The crystal-to-detector distance was 3.8 cm, and the data collection was carried out in 512 x 512 pixel mode. The initial unit-cell parameters were determined by a least-squares fit of the angular setting of strong reflections, collected by a 110.0 degree scan in 110 frames over three different parts of the reciprocal space.

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. All non-H atoms were refined by full-matrix least-squares with anisotropic displacement parameters. The H-atoms were included in calculated positions and treated as riding atoms: aromatic C—H 0.95 Å, methyl C—H 0.98 Å, with U_iso(H) = k x U_eq (parent C-atom), where k = 1.2 for the aromatic H-atoms and 1.5 for the methyl H-atoms.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Re1	0.14601 (2)	0.72963 (2)	0.32787 (2)	0.02121 (7)
S1	−0.14545 (10)	0.69801 (10)	0.32555 (6)	0.0339 (2)
O1	−0.4071 (3)	1.1575 (3)	−0.10292 (17)	0.0319 (6)
O2	0.4460 (3)	0.1858 (3)	0.18698 (18)	0.0312 (6)
O3	−0.3485 (3)	1.5812 (3)	0.11663 (16)	0.0304 (6)
O4	0.4407 (3)	0.8682 (3)	0.61296 (17)	0.0394 (7)
O5	0.1617 (3)	0.4391 (3)	0.36997 (19)	0.0411 (7)
O6	0.4414 (3)	0.6569 (3)	0.3063 (2)	0.0433 (8)
O7	0.1630 (4)	0.6938 (3)	0.51300 (17)	0.0427 (8)
O8	−0.0685 (2)	0.7819 (3)	0.34965 (16)	0.0268 (5)
N1	0.0999 (3)	0.7597 (3)	0.20143 (18)	0.0204 (6)
N2	−0.0220 (3)	0.9804 (3)	0.19183 (17)	0.0194 (6)
N3	0.1135 (3)	0.9387 (3)	0.30388 (19)	0.0202 (6)
C1	0.0084 (3)	0.8671 (3)	0.1689 (2)	0.0204 (7)
C2	−0.0499 (3)	0.8346 (3)	0.1057 (2)	0.0206 (7)
C3	0.0075 (3)	0.7082 (3)	0.1024 (2)	0.0221 (7)
H3	−0.0121	0.6579	0.0679	0.027*
C4	0.1005 (3)	0.6663 (3)	0.1591 (2)	0.0203 (7)
C5	−0.1449 (3)	0.9182 (3)	0.0524 (2)	0.0213 (7)
C6	−0.1692 (4)	1.0518 (4)	0.0414 (2)	0.0268 (7)
H6	−0.1252	1.0911	0.0707	0.032*
C7	−0.2554 (4)	1.1273 (4)	−0.0110 (2)	0.0279 (8)
H7	−0.2698	1.2178	−0.0176	0.034*
C8	−0.3216 (4)	1.0731 (4)	−0.0541 (2)	0.0249 (7)
C9	−0.2988 (4)	0.9411 (4)	−0.0452 (3)	0.0320 (8)
H9	−0.3427	0.9024	−0.0750	0.038*
C10	−0.2112 (4)	0.8657 (4)	0.0077 (3)	0.0295 (8)
H10	−0.1959	0.7752	0.0135	0.035*
C11	0.1921 (3)	0.5424 (3)	0.1676 (2)	0.0211 (7)
C12	0.3237 (3)	0.5342 (3)	0.1702 (2)	0.0222 (7)
H12	0.3537	0.6100	0.1675	0.027*
C13	0.4115 (4)	0.4165 (3)	0.1767 (2)	0.0239 (7)
H13	0.5008	0.4119	0.1785	0.029*
C14	0.3673 (4)	0.3057 (3)	0.1806 (2)	0.0232 (7)
C15	0.2365 (4)	0.3122 (3)	0.1775 (2)	0.0251 (7)
H15	0.2067	0.2363	0.1800	0.030*
C16	0.1502 (4)	0.4299 (4)	0.1707 (2)	0.0241 (7)
H16	0.0611	0.4343	0.1680	0.029*
C17	0.0258 (3)	1.0153 (3)	0.2495 (2)	0.0199 (6)
C18	−0.0130 (3)	1.1427 (3)	0.2687 (2)	0.0196 (6)
C19	0.0497 (3)	1.1407 (3)	0.3348 (2)	0.0228 (7)
H19	0.0423	1.2102	0.3625	0.027*
C20	0.1271 (3)	1.0161 (3)	0.3540 (2)	0.0209 (7)
C21	−0.1002 (3)	1.2541 (3)	0.2263 (2)	0.0200 (7)
C22	−0.0969 (3)	1.2816 (3)	0.1410 (2)	0.0207 (7)
H22	−0.0383	1.2252	0.1091	0.025*
C23	−0.1777 (4)	1.3898 (3)	0.1015 (2)	0.0230 (7)
H23	−0.1744	1.4067	0.0433	0.028*
C24	−0.2630 (4)	1.4726 (3)	0.1483 (2)	0.0238 (7)
C25	−0.2671 (4)	1.4481 (4)	0.2331 (2)	0.0276 (8)
H25	−0.3251	1.5055	0.2646	0.033*
C26	−0.1866 (4)	1.3398 (4)	0.2722 (2)	0.0257 (7)
H26	−0.1901	1.3236	0.3304	0.031*
C27	0.2131 (3)	0.9766 (3)	0.4195 (2)	0.0222 (7)
C28	0.3401 (4)	0.9074 (4)	0.4074 (2)	0.0264 (7)
H28	0.3734	0.8857	0.3549	0.032*
C29	0.4193 (4)	0.8695 (4)	0.4702 (2)	0.0301 (8)
H29	0.5056	0.8219	0.4607	0.036*
C30	0.3717 (4)	0.9014 (4)	0.5471 (2)	0.0291 (8)
C31	0.2455 (4)	0.9730 (4)	0.5602 (2)	0.0284 (8)
H31	0.2128	0.9950	0.6127	0.034*
C32	0.1683 (4)	1.0119 (4)	0.4968 (2)	0.0247 (7)
H32	0.0837	1.0632	0.5056	0.030*
C33	−0.4777 (5)	1.1060 (4)	−0.1473 (3)	0.0398 (10)
H33A	−0.5377	1.1758	−0.1779	0.060*
H33B	−0.5268	1.0495	−0.1091	0.060*
H33C	−0.4175	1.0570	−0.1858	0.060*
C34	0.5819 (4)	0.1771 (4)	0.1860 (3)	0.0355 (9)
H34A	0.6278	0.0870	0.1916	0.053*
H34B	0.5963	0.2137	0.2316	0.053*
H34C	0.6146	0.2246	0.1339	0.053*
C35	−0.3696 (4)	1.5952 (4)	0.0331 (2)	0.0338 (9)
H35A	−0.4402	1.6695	0.0199	0.051*
H35B	−0.3927	1.5179	0.0244	0.051*
H35C	−0.2903	1.6078	−0.0025	0.051*
C36	0.5689 (4)	0.7921 (5)	0.6029 (3)	0.0450 (11)
H36A	0.6090	0.7781	0.6538	0.068*
H36B	0.6204	0.8364	0.5578	0.068*
H36C	0.5655	0.7093	0.5904	0.068*
C37	0.1555 (4)	0.5470 (4)	0.3509 (2)	0.0303 (8)
C38	0.3302 (4)	0.6873 (4)	0.3121 (2)	0.0319 (9)
C39	0.1581 (4)	0.7109 (4)	0.4416 (3)	0.0311 (9)
C40	−0.2117 (6)	0.6198 (6)	0.4207 (4)	0.0608 (15)
H40A	−0.1460	0.5466	0.4430	0.091*
H40B	−0.2868	0.5898	0.4120	0.091*
H40C	−0.2388	0.6800	0.4594	0.091*
C41	−0.2894 (5)	0.8075 (6)	0.2965 (3)	0.0496 (12)
H41A	−0.2711	0.8584	0.2423	0.074*
H41B	−0.3215	0.8645	0.3369	0.074*
H41C	−0.3552	0.7602	0.2940	0.074*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Re1	0.02337 (11)	0.02141 (10)	0.01819 (10)	0.00039 (6)	−0.00751 (6)	−0.00444 (6)
S1	0.0326 (5)	0.0361 (5)	0.0360 (5)	−0.0096 (4)	−0.0048 (4)	−0.0101 (4)
O1	0.0387 (15)	0.0259 (13)	0.0328 (15)	−0.0011 (11)	−0.0220 (12)	−0.0022 (11)
O2	0.0319 (14)	0.0198 (13)	0.0388 (16)	0.0018 (11)	−0.0091 (12)	−0.0035 (11)
O3	0.0389 (15)	0.0243 (13)	0.0248 (13)	0.0042 (11)	−0.0120 (11)	−0.0036 (10)
O4	0.0327 (15)	0.063 (2)	0.0211 (14)	−0.0027 (14)	−0.0134 (11)	−0.0060 (13)
O5	0.065 (2)	0.0200 (14)	0.0348 (16)	−0.0022 (13)	−0.0139 (14)	−0.0002 (11)
O6	0.0216 (15)	0.056 (2)	0.053 (2)	0.0043 (13)	−0.0103 (13)	−0.0239 (16)
O7	0.071 (2)	0.0401 (17)	0.0172 (14)	−0.0111 (16)	−0.0117 (14)	−0.0025 (12)
O8	0.0239 (13)	0.0282 (13)	0.0283 (14)	−0.0016 (10)	−0.0043 (10)	−0.0088 (11)
N1	0.0199 (14)	0.0192 (14)	0.0212 (14)	0.0005 (11)	−0.0057 (11)	−0.0045 (11)
N2	0.0196 (13)	0.0213 (14)	0.0184 (14)	−0.0024 (11)	−0.0047 (11)	−0.0066 (11)
N3	0.0214 (14)	0.0195 (14)	0.0211 (14)	−0.0016 (11)	−0.0083 (11)	−0.0056 (11)
C1	0.0216 (16)	0.0229 (16)	0.0173 (16)	−0.0026 (13)	−0.0072 (12)	−0.0040 (13)
C2	0.0212 (16)	0.0237 (17)	0.0187 (16)	−0.0040 (13)	−0.0059 (13)	−0.0060 (13)
C3	0.0240 (17)	0.0222 (17)	0.0216 (17)	−0.0022 (13)	−0.0073 (13)	−0.0071 (13)
C4	0.0229 (16)	0.0226 (16)	0.0157 (15)	−0.0026 (13)	−0.0039 (13)	−0.0053 (12)
C5	0.0222 (16)	0.0248 (17)	0.0162 (16)	−0.0019 (13)	−0.0060 (13)	−0.0033 (13)
C6	0.0336 (19)	0.0244 (18)	0.0255 (18)	−0.0056 (15)	−0.0128 (15)	−0.0049 (14)
C7	0.037 (2)	0.0206 (17)	0.0275 (19)	−0.0034 (15)	−0.0125 (16)	−0.0033 (14)
C8	0.0258 (18)	0.0270 (18)	0.0206 (17)	−0.0007 (14)	−0.0078 (14)	−0.0035 (14)
C9	0.038 (2)	0.0288 (19)	0.035 (2)	−0.0031 (16)	−0.0205 (17)	−0.0096 (16)
C10	0.035 (2)	0.0208 (17)	0.036 (2)	−0.0013 (15)	−0.0176 (17)	−0.0078 (15)
C11	0.0240 (17)	0.0213 (16)	0.0178 (16)	−0.0019 (13)	−0.0053 (13)	−0.0043 (13)
C12	0.0270 (17)	0.0208 (16)	0.0195 (16)	−0.0041 (14)	−0.0049 (13)	−0.0046 (13)
C13	0.0230 (17)	0.0252 (18)	0.0230 (17)	−0.0019 (14)	−0.0063 (13)	−0.0045 (14)
C14	0.0287 (18)	0.0194 (16)	0.0191 (17)	0.0007 (14)	−0.0050 (13)	−0.0028 (13)
C15	0.0308 (19)	0.0202 (17)	0.0253 (18)	−0.0075 (14)	−0.0033 (14)	−0.0041 (14)
C16	0.0228 (17)	0.0270 (18)	0.0240 (18)	−0.0055 (14)	−0.0031 (14)	−0.0074 (14)
C17	0.0198 (16)	0.0206 (16)	0.0190 (16)	−0.0019 (13)	−0.0045 (12)	−0.0041 (13)
C18	0.0212 (16)	0.0201 (16)	0.0180 (16)	−0.0035 (13)	−0.0053 (12)	−0.0035 (12)
C19	0.0262 (17)	0.0237 (17)	0.0206 (17)	−0.0043 (14)	−0.0070 (13)	−0.0069 (13)
C20	0.0219 (16)	0.0238 (17)	0.0186 (16)	−0.0046 (13)	−0.0046 (13)	−0.0057 (13)
C21	0.0222 (16)	0.0198 (16)	0.0202 (17)	−0.0048 (13)	−0.0070 (13)	−0.0045 (13)
C22	0.0235 (16)	0.0220 (16)	0.0190 (16)	−0.0053 (13)	−0.0036 (13)	−0.0076 (13)
C23	0.0290 (18)	0.0248 (17)	0.0173 (16)	−0.0079 (14)	−0.0057 (13)	−0.0038 (13)
C24	0.0272 (18)	0.0173 (16)	0.0270 (18)	−0.0011 (13)	−0.0106 (14)	−0.0029 (13)
C25	0.0316 (19)	0.0261 (18)	0.0241 (18)	0.0029 (15)	−0.0070 (15)	−0.0106 (14)
C26	0.0323 (19)	0.0270 (18)	0.0184 (17)	−0.0017 (15)	−0.0077 (14)	−0.0069 (14)
C27	0.0233 (17)	0.0256 (17)	0.0197 (17)	−0.0063 (14)	−0.0062 (13)	−0.0044 (13)
C28	0.0260 (18)	0.0340 (19)	0.0197 (17)	−0.0029 (15)	−0.0054 (14)	−0.0081 (14)
C29	0.0242 (18)	0.041 (2)	0.0260 (19)	−0.0026 (16)	−0.0067 (15)	−0.0093 (16)
C30	0.0278 (19)	0.039 (2)	0.0214 (18)	−0.0057 (16)	−0.0107 (14)	−0.0028 (15)
C31	0.0283 (19)	0.041 (2)	0.0182 (17)	−0.0086 (16)	−0.0027 (14)	−0.0101 (15)
C32	0.0221 (16)	0.0299 (19)	0.0241 (18)	−0.0043 (14)	−0.0049 (14)	−0.0092 (15)
C33	0.048 (3)	0.036 (2)	0.038 (2)	−0.0033 (19)	−0.030 (2)	−0.0014 (18)
C34	0.030 (2)	0.0268 (19)	0.044 (2)	0.0041 (16)	−0.0068 (17)	−0.0036 (17)
C35	0.043 (2)	0.032 (2)	0.0232 (19)	−0.0015 (17)	−0.0147 (17)	0.0029 (16)
C36	0.031 (2)	0.067 (3)	0.032 (2)	−0.002 (2)	−0.0150 (18)	−0.001 (2)
C37	0.033 (2)	0.034 (2)	0.0230 (19)	−0.0007 (16)	−0.0084 (15)	−0.0062 (15)
C38	0.039 (2)	0.032 (2)	0.0258 (19)	−0.0014 (17)	−0.0098 (16)	−0.0105 (16)
C39	0.0272 (19)	0.0216 (18)	0.042 (2)	−0.0024 (15)	−0.0070 (16)	−0.0017 (16)
C40	0.062 (3)	0.052 (3)	0.060 (3)	−0.022 (3)	−0.003 (3)	0.016 (3)
C41	0.035 (2)	0.069 (3)	0.046 (3)	−0.015 (2)	−0.020 (2)	0.002 (2)

Geometric parameters (Å, º)

Re1—O8	2.218 (3)	C14—C15	1.393 (5)
Re1—N1	2.190 (3)	C15—H15	0.9500
Re1—N3	2.188 (3)	C15—C16	1.384 (5)
Re1—C37	1.935 (4)	C16—H16	0.9500
Re1—C38	1.901 (4)	C17—C18	1.441 (5)
Re1—C39	1.894 (4)	C18—C19	1.375 (5)
S1—O8	1.518 (3)	C18—C21	1.468 (5)
S1—C40	1.777 (5)	C19—H19	0.9500
S1—C41	1.772 (5)	C19—C20	1.414 (5)
O1—C8	1.367 (4)	C20—C27	1.471 (5)
O1—C33	1.412 (5)	C21—C22	1.394 (5)
O2—C14	1.368 (4)	C21—C26	1.405 (5)
O2—C34	1.433 (5)	C22—H22	0.9500
O3—C24	1.376 (4)	C22—C23	1.395 (5)
O3—C35	1.422 (5)	C23—H23	0.9500
O4—C30	1.362 (5)	C23—C24	1.389 (5)
O4—C36	1.425 (6)	C24—C25	1.386 (5)
O5—C37	1.146 (5)	C25—H25	0.9500
O6—C38	1.150 (5)	C25—C26	1.391 (5)
O7—C39	1.179 (5)	C26—H26	0.9500
N1—C1	1.407 (4)	C27—C28	1.392 (5)
N1—C4	1.354 (4)	C27—C32	1.403 (5)
N2—C1	1.322 (5)	C28—H28	0.9500
N2—C17	1.319 (4)	C28—C29	1.386 (5)
N3—C17	1.407 (4)	C29—H29	0.9500
N3—C20	1.352 (5)	C29—C30	1.389 (5)
C1—C2	1.450 (5)	C30—C31	1.396 (6)
C2—C3	1.377 (5)	C31—H31	0.9500
C2—C5	1.471 (5)	C31—C32	1.382 (5)
C3—H3	0.9500	C32—H32	0.9500
C3—C4	1.414 (5)	C33—H33A	0.9800
C4—C11	1.461 (5)	C33—H33B	0.9800
C5—C6	1.397 (5)	C33—H33C	0.9800
C5—C10	1.390 (5)	C34—H34A	0.9800
C6—H6	0.9500	C34—H34B	0.9800
C6—C7	1.374 (5)	C34—H34C	0.9800
C7—H7	0.9500	C35—H35A	0.9800
C7—C8	1.384 (5)	C35—H35B	0.9800
C8—C9	1.385 (5)	C35—H35C	0.9800
C9—H9	0.9500	C36—H36A	0.9800
C9—C10	1.388 (5)	C36—H36B	0.9800
C10—H10	0.9500	C36—H36C	0.9800
C11—C12	1.397 (5)	C40—H40A	0.9800
C11—C16	1.398 (5)	C40—H40B	0.9800
C12—H12	0.9500	C40—H40C	0.9800
C12—C13	1.391 (5)	C41—H41A	0.9800
C13—H13	0.9500	C41—H41B	0.9800
C13—C14	1.391 (5)	C41—H41C	0.9800
N1—Re1—O8	80.47 (10)	C19—C18—C21	126.2 (3)
N3—Re1—O8	79.58 (10)	C18—C19—H19	126.3
N3—Re1—N1	82.82 (11)	C18—C19—C20	107.4 (3)
C37—Re1—O8	94.49 (14)	C20—C19—H19	126.3
C37—Re1—N1	96.02 (14)	N3—C20—C19	111.5 (3)
C37—Re1—N3	174.07 (14)	N3—C20—C27	124.5 (3)
C38—Re1—O8	178.17 (13)	C19—C20—C27	124.0 (3)
C38—Re1—N1	101.08 (14)	C22—C21—C18	122.3 (3)
C38—Re1—N3	99.62 (15)	C22—C21—C26	118.1 (3)
C38—Re1—C37	86.32 (18)	C26—C21—C18	119.5 (3)
C39—Re1—O8	90.76 (14)	C21—C22—H22	119.2
C39—Re1—N1	171.23 (14)	C21—C22—C23	121.6 (3)
C39—Re1—N3	95.42 (14)	C23—C22—H22	119.2
C39—Re1—C37	84.84 (16)	C22—C23—H23	120.4
C39—Re1—C38	87.68 (17)	C24—C23—C22	119.1 (3)
O8—S1—C40	104.3 (2)	C24—C23—H23	120.4
O8—S1—C41	103.4 (2)	O3—C24—C23	124.6 (3)
C41—S1—C40	98.1 (3)	O3—C24—C25	115.1 (3)
C8—O1—C33	117.5 (3)	C25—C24—C23	120.3 (3)
C14—O2—C34	117.0 (3)	C24—C25—H25	119.8
C24—O3—C35	117.1 (3)	C24—C25—C26	120.3 (3)
C30—O4—C36	117.6 (3)	C26—C25—H25	119.8
S1—O8—Re1	118.41 (15)	C21—C26—H26	119.8
C1—N1—Re1	121.8 (2)	C25—C26—C21	120.4 (3)
C4—N1—Re1	125.7 (2)	C25—C26—H26	119.8
C4—N1—C1	105.9 (3)	C28—C27—C20	122.3 (3)
C17—N2—C1	127.3 (3)	C28—C27—C32	117.9 (3)
C17—N3—Re1	121.8 (2)	C32—C27—C20	119.8 (3)
C20—N3—Re1	128.0 (2)	C27—C28—H28	119.2
C20—N3—C17	105.7 (3)	C29—C28—C27	121.5 (3)
N1—C1—C2	109.4 (3)	C29—C28—H28	119.2
N2—C1—N1	126.2 (3)	C28—C29—H29	120.2
N2—C1—C2	124.4 (3)	C28—C29—C30	119.6 (4)
C1—C2—C5	128.4 (3)	C30—C29—H29	120.2
C3—C2—C1	105.4 (3)	O4—C30—C29	124.4 (4)
C3—C2—C5	126.1 (3)	O4—C30—C31	115.8 (3)
C2—C3—H3	126.0	C29—C30—C31	119.8 (3)
C2—C3—C4	108.1 (3)	C30—C31—H31	120.0
C4—C3—H3	126.0	C32—C31—C30	120.0 (3)
N1—C4—C3	111.1 (3)	C32—C31—H31	120.0
N1—C4—C11	123.8 (3)	C27—C32—H32	119.5
C3—C4—C11	124.9 (3)	C31—C32—C27	121.0 (3)
C6—C5—C2	122.6 (3)	C31—C32—H32	119.5
C10—C5—C2	120.3 (3)	O1—C33—H33A	109.5
C10—C5—C6	117.1 (3)	O1—C33—H33B	109.5
C5—C6—H6	119.4	O1—C33—H33C	109.5
C7—C6—C5	121.2 (3)	H33A—C33—H33B	109.5
C7—C6—H6	119.4	H33A—C33—H33C	109.5
C6—C7—H7	119.6	H33B—C33—H33C	109.5
C6—C7—C8	120.9 (3)	O2—C34—H34A	109.5
C8—C7—H7	119.6	O2—C34—H34B	109.5
O1—C8—C7	115.7 (3)	O2—C34—H34C	109.5
O1—C8—C9	124.9 (3)	H34A—C34—H34B	109.5
C7—C8—C9	119.4 (3)	H34A—C34—H34C	109.5
C8—C9—H9	120.4	H34B—C34—H34C	109.5
C8—C9—C10	119.3 (3)	O3—C35—H35A	109.5
C10—C9—H9	120.4	O3—C35—H35B	109.5
C5—C10—H10	118.9	O3—C35—H35C	109.5
C9—C10—C5	122.3 (3)	H35A—C35—H35B	109.5
C9—C10—H10	118.9	H35A—C35—H35C	109.5
C12—C11—C4	120.8 (3)	H35B—C35—H35C	109.5
C12—C11—C16	118.7 (3)	O4—C36—H36A	109.5
C16—C11—C4	120.5 (3)	O4—C36—H36B	109.5
C11—C12—H12	119.5	O4—C36—H36C	109.5
C13—C12—C11	120.9 (3)	H36A—C36—H36B	109.5
C13—C12—H12	119.5	H36A—C36—H36C	109.5
C12—C13—H13	120.3	H36B—C36—H36C	109.5
C14—C13—C12	119.4 (3)	O5—C37—Re1	175.3 (3)
C14—C13—H13	120.3	O6—C38—Re1	176.4 (4)
O2—C14—C13	123.7 (3)	O7—C39—Re1	176.5 (3)
O2—C14—C15	115.8 (3)	S1—C40—H40A	109.5
C13—C14—C15	120.5 (3)	S1—C40—H40B	109.5
C14—C15—H15	120.2	S1—C40—H40C	109.5
C16—C15—C14	119.6 (3)	H40A—C40—H40B	109.5
C16—C15—H15	120.2	H40A—C40—H40C	109.5
C11—C16—H16	119.5	H40B—C40—H40C	109.5
C15—C16—C11	120.9 (3)	S1—C41—H41A	109.5
C15—C16—H16	119.5	S1—C41—H41B	109.5
N2—C17—N3	128.0 (3)	S1—C41—H41C	109.5
N2—C17—C18	122.7 (3)	H41A—C41—H41B	109.5
N3—C17—C18	109.2 (3)	H41A—C41—H41C	109.5
C17—C18—C21	127.7 (3)	H41B—C41—H41C	109.5
C19—C18—C17	106.2 (3)
Re1—N1—C1—N2	28.0 (5)	C11—C12—C13—C14	0.0 (5)
Re1—N1—C1—C2	−151.5 (2)	C12—C11—C16—C15	1.0 (5)
Re1—N1—C4—C3	148.9 (2)	C12—C13—C14—O2	179.9 (3)
Re1—N1—C4—C11	−35.2 (5)	C12—C13—C14—C15	0.4 (5)
Re1—N3—C17—N2	−18.6 (5)	C13—C14—C15—C16	−0.2 (5)
Re1—N3—C17—C18	158.2 (2)	C14—C15—C16—C11	−0.6 (6)
Re1—N3—C20—C19	−155.4 (2)	C16—C11—C12—C13	−0.8 (5)
Re1—N3—C20—C27	25.4 (5)	C17—N2—C1—N1	−0.6 (6)
O1—C8—C9—C10	−178.7 (4)	C17—N2—C1—C2	178.8 (3)
O2—C14—C15—C16	−179.7 (3)	C17—N3—C20—C19	0.8 (4)
O3—C24—C25—C26	178.9 (3)	C17—N3—C20—C27	−178.4 (3)
O4—C30—C31—C32	179.6 (4)	C17—C18—C19—C20	1.4 (4)
N1—C1—C2—C3	0.4 (4)	C17—C18—C21—C22	−40.6 (5)
N1—C1—C2—C5	−176.5 (3)	C17—C18—C21—C26	142.2 (4)
N1—C4—C11—C12	−43.9 (5)	C18—C19—C20—N3	−1.4 (4)
N1—C4—C11—C16	138.1 (4)	C18—C19—C20—C27	177.7 (3)
N2—C1—C2—C3	−179.1 (3)	C18—C21—C22—C23	−178.0 (3)
N2—C1—C2—C5	4.0 (6)	C18—C21—C26—C25	177.9 (3)
N2—C17—C18—C19	176.0 (3)	C19—C18—C21—C22	138.5 (4)
N2—C17—C18—C21	−4.8 (6)	C19—C18—C21—C26	−38.7 (5)
N3—C17—C18—C19	−1.0 (4)	C19—C20—C27—C28	−133.5 (4)
N3—C17—C18—C21	178.2 (3)	C19—C20—C27—C32	44.8 (5)
N3—C20—C27—C28	45.6 (5)	C20—N3—C17—N2	−176.7 (3)
N3—C20—C27—C32	−136.1 (4)	C20—N3—C17—C18	0.1 (4)
C1—N1—C4—C3	−2.7 (4)	C20—C27—C28—C29	−179.1 (4)
C1—N1—C4—C11	173.3 (3)	C20—C27—C32—C31	178.1 (3)
C1—N2—C17—N3	−4.6 (6)	C21—C18—C19—C20	−177.8 (3)
C1—N2—C17—C18	179.0 (3)	C21—C22—C23—C24	0.4 (5)
C1—C2—C3—C4	−2.0 (4)	C22—C21—C26—C25	0.6 (5)
C1—C2—C5—C6	16.5 (6)	C22—C23—C24—O3	−179.1 (3)
C1—C2—C5—C10	−166.1 (4)	C22—C23—C24—C25	0.4 (5)
C2—C3—C4—N1	3.0 (4)	C23—C24—C25—C26	−0.6 (6)
C2—C3—C4—C11	−172.9 (3)	C24—C25—C26—C21	0.1 (6)
C2—C5—C6—C7	177.9 (4)	C26—C21—C22—C23	−0.8 (5)
C2—C5—C10—C9	−178.1 (4)	C27—C28—C29—C30	−0.3 (6)
C3—C2—C5—C6	−159.8 (4)	C28—C27—C32—C31	−3.5 (6)
C3—C2—C5—C10	17.6 (6)	C28—C29—C30—O4	179.5 (4)
C3—C4—C11—C12	131.5 (4)	C28—C29—C30—C31	−1.0 (6)
C3—C4—C11—C16	−46.5 (5)	C29—C30—C31—C32	0.0 (6)
C4—N1—C1—N2	−179.1 (3)	C30—C31—C32—C27	2.3 (6)
C4—N1—C1—C2	1.4 (4)	C32—C27—C28—C29	2.6 (6)
C4—C11—C12—C13	−178.8 (3)	C33—O1—C8—C7	−179.3 (4)
C4—C11—C16—C15	179.1 (3)	C33—O1—C8—C9	0.2 (6)
C5—C2—C3—C4	175.0 (3)	C34—O2—C14—C13	−2.7 (5)
C5—C6—C7—C8	0.4 (6)	C34—O2—C14—C15	176.8 (3)
C6—C5—C10—C9	−0.6 (6)	C35—O3—C24—C23	13.5 (5)
C6—C7—C8—O1	178.6 (4)	C35—O3—C24—C25	−166.0 (3)
C6—C7—C8—C9	−1.0 (6)	C36—O4—C30—C29	−2.1 (6)
C7—C8—C9—C10	0.8 (6)	C36—O4—C30—C31	178.3 (4)
C8—C9—C10—C5	0.0 (7)	C40—S1—O8—Re1	110.0 (3)
C10—C5—C6—C7	0.4 (6)	C41—S1—O8—Re1	−147.8 (2)