Distorted octa­hedral environments in tri­carbonyl­rhenium(I) complexes of 5-[2-(2,4,6-tri­methyl­phenyl)diazen-1-yl]quinolin-8-olate and 5,7-bis­[2-(2-methyl­phenyl)diazen-1-yl]quinolin-8-olate

The Re^I centres of two Re^I–tricarbonyl complexes, viz. tricarbonyl(pyridine-κN){5-[2-(2,4,6-tri­methyl­phenyl)diazen-1-yl]quinolin-8-olato-κ²N¹,O}rhenium(I), [Re(C₂₃H₂₁N₄O)(CO)₃], (I), and {5,7-bis­[2-(2-methylphenyl)diazen-1-yl]quino­lin-8-ol­ato-κ²N¹,O}tricarbonyl(pyridine-κN)rhenium(I), [Re(C₂₈H₂₃N₆O)(CO)₃], (II), are facially surrounded by three carbonyl ligands, a pyridine ligand and either a 5-[2-(2,4,6-tri­methyl­phenyl)diazen-1-yl]quinolin-8-olate [in (I)] or a 5,7-bis­[2-(2-methyl­phenyl)diazen-1-yl]quinolin-8-olate [in (II)] ligand, in a slightly distorted octa­hedral environment. The crystal structure of (I) is stabilized by two inter­molecular C—H...O inter­actions and that of (II) is stabilized by three inter­molecular C—H...O hydrogen-bonding inter­actions.

S1. Introduction

There is ongoing inter­est in the physiological action of certain derivatives of quinoline and acridine. Preliminary results on the potential anti­cancer properties of 5-[2-(2,4,6-tri­methyl­phenyl)­diazen-1-yl]-8-hy­droxy­quinolin-8-ol and 5,7-bis­[2-(2-methyl­phenyl)­diazen-1-yl]quinolin-8-ol are considered promising (Pretorius, 2011). In this paper, we report the preparation of a 5- and 5,7-coordinated quinolin-8-ol ligand system, together with the crystal structures of the tri­carbonyl­rhenium(I) complexes thereof.

Bidentate ligand systems play an important role in catalysis (van Leeuwen et al., 2003), and can influence the reaction rate and selectivity of most metal complexes. Quinolin-8-ol mostly binds to metal ions in a bidentate fashion (McCleverty & Meyer, 2004). It has attracted inter­est in industrial applications, showing potential as an extracting agent for metal ions in dilute solutions (Farajzadeh et al., 2009). The bidentate ligand quinolin-8-ol can complex to a variety of metal ions, either as a neutral molecule or, more commonly, as a deprotonated anion with the loss of the hy­droxy H atom (Maiti et al., 2005; Colquhoun et al., 2002; Xiang et al., 2011). In this type of complexation, the pyridine N atom and the phenolate O atom act as N and O electron donors to the metal centre, resulting in the formation of a five-membered chelate ring. Quinolin-8-ol and some of its derivatives are well proven precipitation agents and complexants in chemical analysis that are known to form well defined chelate complexes with many ions of main group and transition metals. Quinolin-8-ol has also been used as a structural element to synthesise noncyclic crown-type compounds, yielding crystalline complexes with alkali and alkaline earth metal ions. In the field of organic light-emitting devices (OLEDs), Tang & Van Slyke (1987) were the first to use tris­(quinolin-8-olato)aluminium as an efficient green electroluminescent material. Quinolin-8-ol exhibits a powerful chelating capability and its luminescence properties are tuneable through appropriate substitutions. In OLEDs, the metal coordination compound also acts as an electron-transport material and it has been suggested that such abilities arise from π–π inter­actions between adjacent molecules (Sapochak et al., 1996). La Deda et al. (2004) designed a range of phenyl­diazenyl derivatives of quinolin-8-ol substituted at the 5-position to obtain materials with enhanced electron-transport properties. Quinolin-8-ol species also display enhanced noncentrosymmetry due to the lack of rotational symmetry, an essential property for exhibiting nonlinear optical (NLO) activity. Baul and co-workers (Baul, Mizar, Song et al., 2006; Baul, Mizar, Lycka et al., 2006; Baul, Mizar, Chandra et al., 2008; Baul, Mizar, Rivarola et al., 2008) have synthesized relevant tin(IV) complexes, while Chen et al. (2007) have prepared and reported similar ligand systems. As part of our study of different bidentate ligand systems, two different quinolin-8-ol ligands were synthesised by functionalizing position 5 and/or 7 of the quinolin-8-ol backbone with diazenyl substituents to give 5-[2-(2,4,6-tri­methyl­phenyl)­diazen-1-yl]quinolin-8-ol and 5,7-bis­[2-(2-methyl­phenyl)­diazen-1-yl]quinolin-8-ol. These functionalizations were performed to change the donor and acceptor character of the pyridine and benzene rings. Functionalization of the quinoline backbone might also influence the electronic properties of the ring system or the coordination behaviour towards metal centres. These ligand systems are the first of their kind, with the only other similar structures having functionalities at the 4-position. Such related ligand systems have only been complexed with Sn, Cd, Pb and Mn, making the two title rhenium structures, (I) and (II), the first of their kind to be reported.

S2. Experimental

S2.1. Synthesis and crystallization

5-[2-(2,4,6-Tri­methyl­phenyl)­diazen-1-yl]quinolin-8-ol was prepared as described by van Rensburg (2008). Spectroscopic analysis: ¹³C NMR (600 MHz, C₅D₅N, δ, p.p.m.): 149.56, 149.23, 140.77, 139.64, 138.94, 132.84, 132.53, 130.90, 128.85, 123.43, 115.08, 112.62, 21.34, 20.37; IR (ATR, ν, cm^-1): 1510 (diazenyl, vs).

5,7-Bis[2-(2-methyl­phenyl)­diazen-1-yl]quinolin-8-ol was prepared via bis-azo-coupling between aromatic diazo­nium ions and quinolin-8-ol in a manner based on the synthesis of mono-azo-quinolin-8-ol substitution described by La Deda et al. (2004). Hydro­chloric acid (12 M, 2 ml) was slowly added to a stirred solution of o-toluidine (0.716 g, 6.682 mmol) in water (10 ml). The resulting solution was cooled in an ice bath and an aqueous sodium nitrite (0.5 g, 7.246 mmol) solution (10 ml) was added dropwise. The diazo­nium chloride which formed was then coupled with quinolin-8-ol (0.49 g, 3.375 mmol) dissolved in ethanol (50 ml) and aqueous sodium hydroxide (50 ml, 15.401 mmol), and the reaction mixture was stirred for 1 h at 273 K. The resulting suspension was acidified [To what pH?] with dilute hydro­chloric acid (2 ml) and allowed to reach room temperature. The precipitate that formed was collected by filtration and washed with a water (40 ml) and ethanol (40 ml) mixture, dried, and used without further purification. Spectroscopic analysis: ¹³C NMR (600 MHz, C₅D₅N, δ, p.p.m.): 152.59, 152.49, 148.02, 147.79, 141.20, 137.41, 136.82, 133.98, 133.12, 132.88, 132.42, 132.04, 131.94, 131.44, 129.76, 129.43, 126.93, 123.47, 123.30, 116.24, 18.13, 17.91; IR (ATR, ν, cm^-1): 1498 (diazenyl, vs), 1454 (diazenyl, vs).

Complex (I) was prepared by dissolving (NEt₄)₂[Re(CO)₃Br₃] (30 mg, 0.0389 mmol), prepared according to the method of Alberto et al. (1996), in methanol (10 ml). 5-[2-(2,4,6-Tri­methyl­phenyl)­diazen-1-yl]quinolin-8-ol (11.4 mg, 0.0389 mmol) was added to the solution as a solid and the mixture was stirred overnight at room temperature. The precipitate which formed was filtered off, dried and dissolved in pyridine. Brown plate-like crystals of (I) were obtained. Spectroscopic analysis: ¹³C NMR (600 MHz, C₅D₅N, δ, p.p.m.): 155.01, 152.25, 149.83, 142.76, 139.47, 138.32, 135.50, 132.11, 130.79, 130.33, 128.70, 126.45, 124.30, 123.48, 118.06, 116.54, 23.01, 21.30, 20.24; IR (ATR, ν, cm^-1): 2018 (CO, vs), 1900 (CO, vs), 1507 (diazenyl, vs).

Complex (II) was synthesized by dissolving (NEt₄)₂[Re(CO)₃Br₃] (30 mg, 0.0389 mmol) in methanol (10 ml). 5,7-Bis[2-(2-methyl­phenyl)­diazen-1-yl]quinolin-8-ol (14.4 mg, 0.0389 mmol) was added to the solution and the mixture was stirred for 24 h. The red precipitate which formed was dried and dissolved in pyridine to yield red cuboidal crystals of (II). Spectroscopic analysis: 13^C NMR (600 MHz, C₅D₅N, δ, p.p.m.): 155.97, 151.50, 150.78, 140.42, 137.11, 136.45, 132.94, 129.65, 129.49, 129.33, 127.56, 127.43, 125.09, 124.43, 117.68, 117.14, 105.13, 98.60, 19.019; IR (ATR, ν, cm^-1): 2022 (CO, vs), 1894 (CO, vs), 1501 (diazenyl, vs), 1449 (diazenyl, vs).

S2.2. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 1. For (I) and (II), all H atoms were positioned in geometrically idealized positions and constrained to ride on their parent atoms, with C—H = 0.95 Å and U_iso(H) = 1.2U_eq(C) for sp² CH, and with C—H = 0.98 Å and U_iso(H) = 1.5U_eq(C) for methyl groups. For (I), a large residual electron-density peak is present less than 1 Å from the Re centre. This feature was not improved by the use of alternative data processing or absorption correction methods. For (II), the pyridine ligand was modelled as disordered over two sites. To obtain chemically reasonable geometries required restraint of the geometry of the minor disorder component to be similar to that of the major component and imposition of restraints upon the displacement parameters of the pyridine ring. This gave a total of 60 restraints.

S3. Results and discussion

In the crystal structures of both tri­carbonyl­(pyridine-κN){5-[2-(2,4,6-tri­methyl­phenyl)­diazen-1-yl]quinolin-8-olato-κ²N¹,O}rhenium(I), (I) (Fig. 1), and tri­carbonyl­(pyridine-κN){5,7-bis­[2-(2-methyl­phenyl)­diazen-1-yl]quinolin-8-olato-κ²N¹,O}rhenium(I), (II) (Fig. 2), the o­cta­hedral fac geometries are slightly distorted, with chelate N1—Re—O4 bite angles of 76.85 (14) and 76.35 (7)°, and C3—Re—N2 angles of 176.50 (18) and 175.9 (3)°, respectively. This compares well with the similar structure, fac-[Re(2,4-Quin)(CO)₃(Py)] (2,4-Quin is 2-carboxyl­ato­quinoline-4-carb­oxy­lic acid and Py is pyridine) reported by Schutte et al. (2011), with a chelate bite angle of 75.66° and a carbonyl–Re–N(Py) angle of 178.01°. The chelate bite angle also compares well with those of the diazenylquiniolin-8-ol ligands reported by Baul and co-workers (Baul, Mizar, Song et al., 2006; Baul, Mizar, Lycka et al., 2006; Baul, Mizar, Chandra et al., 2008; Baul, Mizar, Rivarola et al., 2008), which range between 75.18 (4) and 73.53 (4)°.

In both (I) and (II), the pyridine ligands are slightly bent towards the bidentate ligands, with N2—Re—O4 angles of 82.00 (13) and 81.1 (3)°, respectively. This same `bending' is observed in the structure of fac-[Re(2,4-Quin)(CO)₃(Py)], with an equivalent N—Re—O angle of 80.85°. Note, though, that structure (II) exhibits disorder of the pyridine ligand, with refined site-occupancy factors of 0.707 (12) and 0.293 (12). The Re—CO distances of (I) vary between 1.909 (5) and 1.924 (5) Å and those of (II) between 1.894 (3) and 1.922 (3) Å. These are well within the range of distances seen for other tri­carbonyl­rhenium(I) structures (Schutte & Visser, 2008; Schutte et al., 2007, 2008, 2009, 2010, 2011; Schutte et al., 2012a,b; Schutte, Brink et al., 2012). The Re—O bond lengths for the quinolin-8-ol ligands are almost equal at 2.121 (3) and 2.1256 (16) Å for (I) and (II), respectively, while the Re—N bond lengths are also similar at 2.179 (4) and 2.163 (2) Å, respectively. Inter­estingly, whilst the Re—N and Re—O bond lengths are quite similar in both (I) and (II), this was not found for related Sn complexes, where the Sn—O and Sn—N bond lengths reported by Baul and co-workers (Baul, Mizar, Song et al., 2006; Baul, Mizar, Lycka et al., 2006; Baul, Mizar, Chandra et al., 2008; Baul, Mizar, Rivarola et al., 2008) differed by 0.2 to 0.3 Å.

The diazenyl N═N bond lengths of (II) are 1.271 (3) and 1.262 (3) Å, while that of (I) is 1.256 (6) Å. These values are again within the range found for structures reported by Baul and co-workers (Baul, Mizar, Song et al., 2006; Baul, Mizar, Lycka et al., 2006; Baul, Mizar, Chandra et al., 2008; Baul, Mizar, Rivarola et al., 2008) and compare well with similar distances in free ligands.

In (I), the dihedral angle formed between the plane of the 2,4,6-tri­methyl­phenyl ring (C31–C36; r.m.s. deviation = 0.0092 Å) and the plane of the oxygen-substituted ring of the quinolin-8-ol ligand (C24–C29; r.m.s. deviation = 0.0115 Å) is 2.44 (35)° [Is such a large s.u. correct?]. A near coplanar conformation is also seen in (II), as is shown by the angle between the plane of the (2-methyl­phenyl)­diazenyl ring (C21–C26; r.m.s. deviation = 0.0040 Å) and the oxygen-bearing ring of the quinolin-8-ol ligand (C14–C19, r.m.s. deviation = 0.0103 Å) of 3.05 (15)°. Meanwhile, the dihedral angle between the plane of the C31–C36 ring (r.m.s. deviation = 0.0130 Å) and the C14–C19 ring is slightly larger, at 6.24 (15)°. The Re—N(pyridine) bond length is 2.217 (4) Å for (I), while the Re—N bond lengths of disordered (II) are 2.164 (8) and 2.334 (19) Å. These all compare well with similar complexes with tropolone and 2,4-di­quinoline, where bond lengths of 2.208 (4) (Schutte et al., 2012a) and 2.203 (4) Å were reported (Schutte et al., 2011).

Two inter­molecular C—H···O inter­actions are observed in the crystal structure of (I) (see Table 2). The pyridine ligand forms C—H···O inter­actions with the carbonyl O atoms of neighbouring molecules. A short O4···C14^?? inter­action [3.205 (6) Å; Please give symmetry operator] is also observed between neighbouring molecules in (I), and this inter­action results in an infinite one-dimensional chain being formed by the translation of molecules along the [010] vector (Fig. 3). The structure of (II) displays three inter­molecular C—H···O inter­actions (Table 3). As atom C41 is part of the disordered pyridine ligand, some care needs to be taken with inter­preting the detail here. However, as with (I), it can be seen that the pyridine ligand forms inter­molecular C—H···O inter­actions with neighbouring molecules, in this case one with the coordinated O atom of the bidentate ligand and another with a carbonyl O atom. Lastly, an inter­molecular C—H···O inter­action is observed between the quinolin-8-ol backbone and a carbonyl O atom of a neighbouring molecule. Similarly to (I), the structure of (II) also exhibits a Py-to-chelate inter­action [O4···C44^?? = 3.166 (8) Å; Please give symmetry operator], which results in an infinite one-dimensional chain of molecules propagating by translation symmetry, in this case parallel to the a axis (Fig. 4).

The CO stretching frequencies of (I) (2018 and 1900 cm^-1) and (II) (2022 and 1894 cm^-1) are comparable with a similar pyridine complex, that of fac-[Re(2,4-Quin)(CO)₃(Py)], which were reported as 2024, 1926 and 1869 cm^-1 (Schutte et al. 2011). As has been described previously, if the electron density on the metal centre increases due to the donating capabilities of the bidentate ligand, the backbonding into the CO anti­bonding orbitals increases and therefore lowers the observed IR stretching frequencies (Schutte et al. 2011; Schutte et al., 2012a, Schutte et al., 2012b or Schutte, Brink et al., 2012 ?). However, it is not clear that (I) and (II) behave in this fashion. The quinoline backbone cores are the same for 5-[2-(2,4,6-tri­methyl­phenyl)­diazen-1-yl]quinolin-8-olate in (I) and 5,7-bis­[2-(2-methyl­phenyl)­diazen-1-yl]quinolin-8-olate in (II), with the only difference being the substituents. Theoretically, 5,7-bis­[2-(2-methyl­phenyl)­diazen-1-yl]quinolin-8-olate has more electron donation because of the second diazenyl-substituted ring on the backbone, but this cannot be seen in the IR stretching frequencies of (I) and (II), where (I) should in theory have a higher symmetric CO stretching frequency than (II). This might be explained by the fact that these electron-donating substituents are situated some distance from the metal centre itself.

Related literature

For related literature, see: Alberto et al. (1996); Baul, Mizar, Chandra, Song, Eng, Jirasko, Holcapek, de Vos & Linden (2008); Baul, Mizar, Lycka, Rivarola, Jirasko, Holcapek, de Vos & Englert (2006); Baul, Mizar, Rivarola & Englert (2008); Baul, Mizar, Song, Eng, Jirasko, Holcapek, Willem, Biesemans, Verbruggen & Butcher (2006); Chen et al. (2007); Colquhoun et al. (2002); Farajzadeh et al. (2009); La Deda, Grisolia, Aiello, Crispini, Ghedini, Belvisio, Amati & Lelj (2004); Leeuwen et al. (2003); Maiti et al. (2005); McCleverty & Meyer (2004); Pretorius (2011); Sapochak et al. (1996); Schutte & Visser (2008); Schutte et al. (2007, 2009, 2010, 2011, 2012, 2012a, 2012b); Schutte, Visser & Roodt (2008); Tang & Van Slyke (1987); Xiang et al. (2011); van Rensburg (2008).

Computing details

For both compounds, data collection: APEX2 (Bruker, 2008); cell refinement: SAINT-Plus (Bruker, 2008); data reduction: SAINT-Plus (Bruker, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008). Program(s) used to refine structure: SHELXS97 (Sheldrick, 2008) for 12hmsc1_0ma; SHELXL97 (Sheldrick, 2008) for 10lmsc12_0m. Molecular graphics: DIAMOND (Brandenburg & Putz, 2005) for 12hmsc1_0ma; SHELXTL (Sheldrick, 2008) for 10lmsc12_0m. Software used to prepare material for publication: WinGX (Farrugia, 2012) for 12hmsc1_0ma; SHELXTL (Sheldrick, 2008) for 10lmsc12_0m.

Figures

	Fig. 1. The molecular structure of (I), showing the atom-numbering scheme and displacement ellipsoids at the 50% probability level. H atoms have been omitted for clarity.
	Fig. 2. The molecular structure of (II), showing the atom-numbering scheme and displacement ellipsoids at the 50% probability level. H atoms have been omitted for clarity. Both components of the disordered pyridine ligand are shown.
	Fig. 3. A graphical representation of the infinite one-dimensional chains formed by the generation of symmetry-related molecules along the [010] vector in the structure of (I). [Dashed lines indicate hydrogen bonds? Indicate the symmetry operator?]
	Fig. 4. A graphical representation of the infinite one-dimensional chains formed by the generation of symmetry-related molecules along the [100] vector in the structure of (II). [Dashed lines indicate hydrogen bonds? Indicate the symmetry operator?]

(12hmsc1_0ma) Tricarbonyl(pyridine-κN){5-[2-(2,4,6-trimethylphenyl)diazen-1-yl]quinolin-8-olato-κ²N¹,O}rhenium(I)

Crystal data

[Re(C23H21N4O)(CO)3]	F(000) = 1248
Mr = 639.67	Dx = 1.803 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 9930 reflections
a = 23.723 (3) Å	θ = 2.6–28.3°
b = 6.7123 (7) Å	µ = 5.20 mm^−1
c = 14.8382 (17) Å	T = 100 K
β = 94.178 (4)°	Plate, brown
V = 2356.5 (5) Å^3	0.5 × 0.16 × 0.09 mm
Z = 4

Data collection

Bruker APEXII CCD area-detector diffractometer	4678 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.045
ϕ and ω scans	θmax = 28.4°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −31→31
Tmin = 0.391, Tmax = 0.640	k = −8→5
30040 measured reflections	l = −19→19
5833 independent reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.031	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.074	H-atom parameters constrained
S = 1.13	w = 1/[σ^2(Fo^2) + (0.0122P)^2 + 12.6794P] where P = (Fo^2 + 2Fc^2)/3
5833 reflections	(Δ/σ)max = 0.001
319 parameters	Δρmax = 4.32 e Å^−3
0 restraints	Δρmin = −1.58 e Å^−3

Special details

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 (Ų)

	x	y	z	Uiso*/Ueq
C1	0.5703 (2)	0.0612 (7)	0.6417 (3)	0.0230 (10)
C2	0.6119 (2)	0.3853 (7)	0.7257 (3)	0.0245 (10)
C3	0.6737 (2)	0.0455 (8)	0.7223 (3)	0.0264 (10)
C15	0.60654 (19)	0.6023 (7)	0.5162 (3)	0.0239 (10)
H15	0.629	0.6655	0.5635	0.029*
C14	0.5857 (2)	0.7159 (7)	0.4444 (3)	0.0252 (10)
H14	0.5946	0.8537	0.4418	0.03*
C13	0.5515 (2)	0.6280 (7)	0.3758 (3)	0.0250 (10)
H13	0.5365	0.7038	0.3256	0.03*
C12	0.5399 (2)	0.4268 (7)	0.3824 (3)	0.0253 (10)
H12	0.5161	0.3623	0.3371	0.03*
C11	0.56334 (19)	0.3207 (7)	0.4558 (3)	0.0243 (10)
H11	0.5556	0.1821	0.459	0.029*
C21	0.7312 (2)	0.5539 (8)	0.6442 (3)	0.0267 (10)
H21	0.7168	0.5926	0.6996	0.032*
C22	0.7736 (2)	0.6697 (8)	0.6091 (4)	0.0306 (11)
H22	0.7878	0.7839	0.6411	0.037*
C23	0.7947 (2)	0.6188 (8)	0.5290 (4)	0.0300 (11)
H23	0.8226	0.6994	0.5044	0.036*
C24	0.77447 (19)	0.4443 (8)	0.4824 (3)	0.0259 (10)
C29	0.7940 (2)	0.3738 (8)	0.4007 (3)	0.0288 (11)
C28	0.7721 (2)	0.1978 (8)	0.3641 (3)	0.0286 (11)
H28	0.7859	0.1504	0.3095	0.034*
C27	0.7307 (2)	0.0871 (8)	0.4035 (3)	0.0274 (11)
H27	0.7176	−0.0346	0.3768	0.033*
C26	0.70832 (19)	0.1562 (8)	0.4832 (3)	0.0238 (10)
C25	0.73209 (18)	0.3345 (7)	0.5223 (3)	0.0222 (10)
N3	0.83498 (17)	0.4928 (7)	0.3620 (3)	0.0306 (10)
N4	0.84495 (18)	0.4428 (7)	0.2832 (3)	0.0335 (10)
C31	0.8870 (2)	0.5567 (8)	0.2421 (4)	0.0308 (11)
C32	0.9127 (2)	0.7340 (9)	0.2745 (4)	0.0346 (12)
C33	0.9535 (2)	0.8212 (9)	0.2243 (4)	0.0383 (13)
H33	0.9715	0.94	0.2461	0.046*
C34	0.9688 (2)	0.7406 (9)	0.1435 (4)	0.0340 (12)
C35	0.9418 (2)	0.5702 (9)	0.1115 (4)	0.0337 (12)
H35	0.9511	0.5163	0.0553	0.04*
C36	0.9014 (2)	0.4752 (9)	0.1591 (4)	0.0317 (12)
C37	0.8979 (3)	0.8366 (11)	0.3601 (5)	0.059 (2)
H37A	0.9189	0.962	0.3671	0.088*
H37C	0.908	0.7501	0.412	0.088*
H37B	0.8572	0.8642	0.3568	0.088*
C38	1.0149 (3)	0.8377 (10)	0.0941 (4)	0.0468 (15)
H38C	1.0518	0.7976	0.1221	0.07*
H38A	1.0111	0.9829	0.0974	0.07*
H38B	1.0116	0.7957	0.0307	0.07*
C39	0.8734 (2)	0.2880 (10)	0.1216 (4)	0.0436 (15)
H39A	0.8323	0.3049	0.1181	0.065*
H39B	0.8841	0.1754	0.1613	0.065*
H39C	0.8857	0.2621	0.0611	0.065*
N2	0.59658 (15)	0.4047 (6)	0.5228 (3)	0.0196 (8)
N1	0.71074 (15)	0.3925 (6)	0.6026 (3)	0.0235 (9)
O1	0.53063 (15)	−0.0338 (5)	0.6480 (2)	0.0311 (8)
O2	0.59666 (16)	0.4896 (5)	0.7805 (3)	0.0344 (9)
O3	0.69356 (16)	−0.0630 (6)	0.7758 (3)	0.0373 (9)
O4	0.66811 (14)	0.0642 (5)	0.5216 (2)	0.0250 (7)
Re1	0.636957 (7)	0.21790 (3)	0.632607 (12)	0.02021 (6)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.030 (3)	0.020 (2)	0.019 (2)	−0.0005 (19)	0.0014 (19)	−0.0035 (18)
C2	0.025 (2)	0.022 (3)	0.027 (3)	−0.0033 (19)	0.0002 (19)	−0.002 (2)
C3	0.027 (2)	0.024 (3)	0.029 (3)	−0.0017 (19)	0.000 (2)	−0.004 (2)
C15	0.023 (2)	0.022 (3)	0.027 (3)	−0.0019 (18)	0.0030 (19)	−0.0049 (19)
C14	0.029 (2)	0.018 (2)	0.029 (3)	−0.0015 (19)	0.0032 (19)	0.000 (2)
C13	0.031 (3)	0.020 (3)	0.024 (2)	0.0024 (19)	0.0015 (19)	0.0016 (19)
C12	0.027 (2)	0.023 (3)	0.025 (3)	−0.0023 (19)	−0.0022 (19)	−0.001 (2)
C11	0.025 (2)	0.022 (3)	0.027 (2)	−0.0039 (18)	0.0027 (19)	−0.0027 (19)
C21	0.026 (2)	0.026 (3)	0.027 (3)	−0.001 (2)	0.001 (2)	−0.004 (2)
C22	0.026 (2)	0.031 (3)	0.034 (3)	−0.007 (2)	−0.002 (2)	−0.008 (2)
C23	0.026 (2)	0.030 (3)	0.034 (3)	−0.005 (2)	0.000 (2)	−0.001 (2)
C24	0.021 (2)	0.030 (3)	0.027 (3)	0.0021 (19)	−0.0015 (19)	0.000 (2)
C29	0.020 (2)	0.037 (3)	0.030 (3)	0.002 (2)	0.0009 (19)	−0.001 (2)
C28	0.026 (2)	0.035 (3)	0.025 (2)	0.005 (2)	0.0027 (19)	−0.006 (2)
C27	0.025 (2)	0.028 (3)	0.028 (3)	0.002 (2)	0.000 (2)	−0.006 (2)
C26	0.019 (2)	0.026 (3)	0.026 (2)	0.0038 (18)	−0.0031 (18)	−0.004 (2)
C25	0.019 (2)	0.025 (3)	0.023 (2)	0.0017 (18)	−0.0008 (17)	−0.0033 (19)
N3	0.024 (2)	0.038 (3)	0.030 (2)	0.0022 (18)	0.0037 (17)	−0.003 (2)
N4	0.026 (2)	0.043 (3)	0.033 (2)	−0.0004 (19)	0.0054 (18)	−0.003 (2)
C31	0.023 (2)	0.038 (3)	0.031 (3)	0.001 (2)	0.000 (2)	0.000 (2)
C32	0.031 (3)	0.041 (3)	0.032 (3)	0.000 (2)	0.006 (2)	−0.004 (2)
C33	0.040 (3)	0.039 (3)	0.036 (3)	−0.007 (2)	0.000 (2)	−0.003 (2)
C34	0.030 (3)	0.041 (3)	0.031 (3)	−0.002 (2)	0.000 (2)	0.007 (2)
C35	0.033 (3)	0.043 (3)	0.025 (3)	−0.002 (2)	−0.002 (2)	−0.001 (2)
C36	0.025 (3)	0.040 (3)	0.030 (3)	−0.002 (2)	−0.002 (2)	−0.001 (2)
C37	0.067 (5)	0.058 (5)	0.055 (4)	−0.026 (4)	0.026 (4)	−0.027 (4)
C38	0.052 (4)	0.048 (4)	0.041 (3)	−0.010 (3)	0.007 (3)	0.006 (3)
C39	0.039 (3)	0.054 (4)	0.039 (3)	−0.013 (3)	0.013 (3)	−0.016 (3)
N2	0.0198 (18)	0.019 (2)	0.0201 (19)	−0.0003 (14)	0.0049 (15)	−0.0011 (15)
N1	0.0191 (19)	0.028 (2)	0.023 (2)	−0.0005 (16)	0.0007 (15)	−0.0048 (17)
O1	0.0307 (19)	0.026 (2)	0.037 (2)	−0.0067 (15)	0.0046 (16)	0.0009 (16)
O2	0.042 (2)	0.027 (2)	0.035 (2)	0.0006 (16)	0.0096 (17)	−0.0090 (16)
O3	0.043 (2)	0.030 (2)	0.037 (2)	0.0026 (17)	−0.0088 (17)	0.0012 (17)
O4	0.0270 (17)	0.0229 (18)	0.0253 (18)	−0.0015 (14)	0.0032 (14)	−0.0056 (14)
Re1	0.02070 (9)	0.01862 (10)	0.02123 (9)	−0.00015 (7)	0.00101 (6)	−0.00218 (8)

Geometric parameters (Å, º)

C1—O1	1.145 (6)	C27—C26	1.409 (7)
C1—Re1	1.913 (5)	C27—H27	0.95
C2—O2	1.151 (6)	C26—O4	1.303 (6)
C2—Re1	1.909 (5)	C26—C25	1.428 (7)
C3—O3	1.153 (6)	C25—N1	1.384 (6)
C3—Re1	1.924 (5)	N3—N4	1.256 (6)
C15—N2	1.352 (6)	N4—C31	1.428 (7)
C15—C14	1.372 (7)	C31—C32	1.406 (8)
C15—H15	0.95	C31—C36	1.412 (7)
C14—C13	1.387 (7)	C32—C33	1.392 (8)
C14—H14	0.95	C32—C37	1.509 (8)
C13—C12	1.383 (7)	C33—C34	1.388 (8)
C13—H13	0.95	C33—H33	0.95
C12—C11	1.384 (7)	C34—C35	1.378 (8)
C12—H12	0.95	C34—C38	1.509 (8)
C11—N2	1.347 (6)	C35—C36	1.386 (7)
C11—H11	0.95	C35—H35	0.95
C21—N1	1.322 (6)	C36—C39	1.508 (8)
C21—C22	1.401 (7)	C37—H37A	0.98
C21—H21	0.95	C37—H37C	0.98
C22—C23	1.366 (7)	C37—H37B	0.98
C22—H22	0.95	C38—H38C	0.98
C23—C24	1.425 (7)	C38—H38A	0.98
C23—H23	0.95	C38—H38B	0.98
C24—C29	1.410 (7)	C39—H39A	0.98
C24—C25	1.412 (7)	C39—H39B	0.98
C29—C28	1.386 (7)	C39—H39C	0.98
C29—N3	1.412 (7)	N2—Re1	2.217 (4)
C28—C27	1.395 (7)	N1—Re1	2.179 (4)
C28—H28	0.95	O4—Re1	2.121 (3)
O1—C1—Re1	179.3 (5)	C34—C33—C32	122.2 (5)
O2—C2—Re1	178.5 (5)	C34—C33—H33	118.9
O3—C3—Re1	176.9 (4)	C32—C33—H33	118.9
N2—C15—C14	123.1 (4)	C35—C34—C33	118.5 (5)
N2—C15—H15	118.4	C35—C34—C38	121.8 (5)
C14—C15—H15	118.4	C33—C34—C38	119.7 (5)
C15—C14—C13	119.5 (5)	C34—C35—C36	121.8 (5)
C15—C14—H14	120.3	C34—C35—H35	119.1
C13—C14—H14	120.3	C36—C35—H35	119.1
C12—C13—C14	118.2 (5)	C35—C36—C31	119.1 (5)
C12—C13—H13	120.9	C35—C36—C39	119.8 (5)
C14—C13—H13	120.9	C31—C36—C39	121.1 (5)
C13—C12—C11	119.2 (5)	C32—C37—H37A	109.5
C13—C12—H12	120.4	C32—C37—H37C	109.5
C11—C12—H12	120.4	H37A—C37—H37C	109.5
N2—C11—C12	123.1 (4)	C32—C37—H37B	109.5
N2—C11—H11	118.5	H37A—C37—H37B	109.5
C12—C11—H11	118.5	H37C—C37—H37B	109.5
N1—C21—C22	122.1 (5)	C34—C38—H38C	109.5
N1—C21—H21	119	C34—C38—H38A	109.5
C22—C21—H21	119	H38C—C38—H38A	109.5
C23—C22—C21	120.1 (5)	C34—C38—H38B	109.5
C23—C22—H22	119.9	H38C—C38—H38B	109.5
C21—C22—H22	119.9	H38A—C38—H38B	109.5
C22—C23—C24	119.8 (5)	C36—C39—H39A	109.5
C22—C23—H23	120.1	C36—C39—H39B	109.5
C24—C23—H23	120.1	H39A—C39—H39B	109.5
C29—C24—C25	118.3 (5)	C36—C39—H39C	109.5
C29—C24—C23	125.0 (5)	H39A—C39—H39C	109.5
C25—C24—C23	116.7 (4)	H39B—C39—H39C	109.5
C28—C29—C24	119.1 (5)	C11—N2—C15	116.9 (4)
C28—C29—N3	124.9 (5)	C11—N2—Re1	120.3 (3)
C24—C29—N3	116.0 (5)	C15—N2—Re1	122.7 (3)
C29—C28—C27	123.0 (5)	C21—N1—C25	119.2 (4)
C29—C28—H28	118.5	C21—N1—Re1	128.2 (3)
C27—C28—H28	118.5	C25—N1—Re1	112.0 (3)
C28—C27—C26	119.8 (5)	C26—O4—Re1	114.7 (3)
C28—C27—H27	120.1	C2—Re1—C1	88.3 (2)
C26—C27—H27	120.1	C2—Re1—C3	90.2 (2)
O4—C26—C27	122.9 (4)	C1—Re1—C3	87.5 (2)
O4—C26—C25	119.9 (4)	C2—Re1—O4	173.00 (17)
C27—C26—C25	117.1 (4)	C1—Re1—O4	97.13 (16)
N1—C25—C24	122.1 (4)	C3—Re1—O4	94.50 (17)
N1—C25—C26	115.3 (4)	C2—Re1—N1	97.37 (17)
C24—C25—C26	122.6 (4)	C1—Re1—N1	172.29 (17)
N4—N3—C29	114.2 (4)	C3—Re1—N1	97.73 (18)
N3—N4—C31	116.1 (5)	O4—Re1—N1	76.85 (14)
C32—C31—C36	120.0 (5)	C2—Re1—N2	93.34 (17)
C32—C31—N4	127.3 (5)	C1—Re1—N2	92.74 (17)
C36—C31—N4	112.7 (5)	C3—Re1—N2	176.50 (18)
C33—C32—C31	118.3 (5)	O4—Re1—N2	82.00 (13)
C33—C32—C37	118.1 (5)	N1—Re1—N2	81.73 (14)
C31—C32—C37	123.6 (5)
N2—C15—C14—C13	1.7 (7)	C14—C15—N2—Re1	174.2 (3)
C15—C14—C13—C12	−0.3 (7)	C22—C21—N1—C25	0.6 (7)
C14—C13—C12—C11	−1.1 (7)	C22—C21—N1—Re1	−169.6 (4)
C13—C12—C11—N2	1.2 (7)	C24—C25—N1—C21	−1.1 (7)
N1—C21—C22—C23	0.8 (8)	C26—C25—N1—C21	178.7 (4)
C21—C22—C23—C24	−1.8 (8)	C24—C25—N1—Re1	170.6 (4)
C22—C23—C24—C29	−178.1 (5)	C26—C25—N1—Re1	−9.6 (5)
C22—C23—C24—C25	1.2 (7)	C27—C26—O4—Re1	−173.9 (4)
C25—C24—C29—C28	−1.6 (7)	C25—C26—O4—Re1	6.8 (5)
C23—C24—C29—C28	177.8 (5)	O2—C2—Re1—C1	−114 (17)
C25—C24—C29—N3	177.9 (4)	O2—C2—Re1—C3	159 (17)
C23—C24—C29—N3	−2.8 (7)	O2—C2—Re1—O4	27 (17)
C24—C29—C28—C27	0.9 (8)	O2—C2—Re1—N1	61 (17)
N3—C29—C28—C27	−178.5 (5)	O2—C2—Re1—N2	−21 (17)
C29—C28—C27—C26	1.6 (8)	O1—C1—Re1—C2	−8E1 (4)
C28—C27—C26—O4	177.4 (4)	O1—C1—Re1—C3	1E1 (4)
C28—C27—C26—C25	−3.3 (7)	O1—C1—Re1—O4	10E1 (4)
C29—C24—C25—N1	179.6 (4)	O1—C1—Re1—N1	14E1 (4)
C23—C24—C25—N1	0.2 (7)	O1—C1—Re1—N2	−18E1 (10)
C29—C24—C25—C26	−0.2 (7)	O3—C3—Re1—C2	94 (8)
C23—C24—C25—C26	−179.6 (4)	O3—C3—Re1—C1	6 (8)
O4—C26—C25—N1	2.2 (6)	O3—C3—Re1—O4	−91 (8)
C27—C26—C25—N1	−177.2 (4)	O3—C3—Re1—N1	−168 (8)
O4—C26—C25—C24	−178.0 (4)	O3—C3—Re1—N2	−87 (9)
C27—C26—C25—C24	2.7 (7)	C26—O4—Re1—C2	25.8 (15)
C28—C29—N3—N4	9.9 (7)	C26—O4—Re1—C1	166.2 (3)
C24—C29—N3—N4	−169.5 (4)	C26—O4—Re1—C3	−105.8 (3)
C29—N3—N4—C31	−178.8 (4)	C26—O4—Re1—N1	−8.9 (3)
N3—N4—C31—C32	−9.5 (8)	C26—O4—Re1—N2	74.4 (3)
N3—N4—C31—C36	171.8 (5)	C21—N1—Re1—C2	4.5 (4)
C36—C31—C32—C33	−2.1 (8)	C25—N1—Re1—C2	−166.2 (3)
N4—C31—C32—C33	179.3 (5)	C21—N1—Re1—C1	141.4 (12)
C36—C31—C32—C37	177.0 (6)	C25—N1—Re1—C1	−29.4 (15)
N4—C31—C32—C37	−1.6 (9)	C21—N1—Re1—C3	−86.6 (4)
C31—C32—C33—C34	0.9 (9)	C25—N1—Re1—C3	102.6 (3)
C37—C32—C33—C34	−178.3 (6)	C21—N1—Re1—O4	−179.5 (4)
C32—C33—C34—C35	1.1 (9)	C25—N1—Re1—O4	9.7 (3)
C32—C33—C34—C38	−177.6 (5)	C21—N1—Re1—N2	96.9 (4)
C33—C34—C35—C36	−2.0 (8)	C25—N1—Re1—N2	−73.9 (3)
C38—C34—C35—C36	176.7 (5)	C11—N2—Re1—C2	−130.1 (4)
C34—C35—C36—C31	0.8 (8)	C15—N2—Re1—C2	54.2 (4)
C34—C35—C36—C39	−179.5 (5)	C11—N2—Re1—C1	−41.6 (4)
C32—C31—C36—C35	1.2 (8)	C15—N2—Re1—C1	142.7 (4)
N4—C31—C36—C35	−180.0 (5)	C11—N2—Re1—C3	52 (3)
C32—C31—C36—C39	−178.5 (5)	C15—N2—Re1—C3	−124 (3)
N4—C31—C36—C39	0.3 (7)	C11—N2—Re1—O4	55.2 (3)
C12—C11—N2—C15	0.2 (7)	C15—N2—Re1—O4	−120.5 (4)
C12—C11—N2—Re1	−175.7 (4)	C11—N2—Re1—N1	133.0 (3)
C14—C15—N2—C11	−1.7 (7)	C15—N2—Re1—N1	−42.7 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C14—H14···O4^i	0.95	2.48	3.205 (6)	133
C12—H12···O1^ii	0.95	2.49	3.139 (6)	126

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

(10lmsc12_0m) {5,7-Bis[2-(2-methylphenyl)diazen-1-yl]quinolin-8-olato-κ²N¹,O}tricarbonyl(pyridine-κN)rhenium(I)

Crystal data

[Re(C28H23N6O)(CO)3]	Z = 2
Mr = 729.75	F(000) = 716
Triclinic, P1	Dx = 1.709 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.9776 (6) Å	Cell parameters from 9973 reflections
b = 11.6818 (8) Å	θ = 2.7–28.0°
c = 15.3994 (11) Å	µ = 4.33 mm^−1
α = 92.113 (4)°	T = 100 K
β = 98.130 (3)°	Cuboid, red
γ = 92.384 (4)°	0.28 × 0.13 × 0.1 mm
V = 1418.13 (18) Å^3

Data collection

Bruker APEXII CCD area-detector diffractometer	6014 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.023
ϕ and ω scans	θmax = 28.2°, θmin = 3.2°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −10→10
Tmin = 0.511, Tmax = 0.648	k = −15→13
21043 measured reflections	l = −20→19
6726 independent reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.022	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.045	H-atom parameters constrained
S = 1.09	w = 1/[σ^2(Fo^2) + (0.0155P)^2 + 0.9052P] where P = (Fo^2 + 2Fc^2)/3
6726 reflections	(Δ/σ)max = 0.002
400 parameters	Δρmax = 1.16 e Å^−3
60 restraints	Δρmin = −1.56 e Å^−3

Special details

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.

Refinement. 7 low angle reflections were omitted due to extremely poor fit between Fo and Fc. It is believed that this was caused by interference from the beam stop.

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 (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
Re1	0.638666 (13)	0.750241 (9)	0.936888 (6)	0.02028 (4)
O4	0.4992 (2)	0.66867 (14)	0.82177 (11)	0.0193 (4)
C1	0.5792 (3)	0.6463 (2)	1.02272 (17)	0.0227 (6)
C2	0.7909 (4)	0.8267 (3)	1.02828 (18)	0.0310 (7)
O1	0.5437 (3)	0.58915 (17)	1.07734 (13)	0.0368 (5)
O2	0.8910 (3)	0.8737 (2)	1.08141 (13)	0.0468 (6)
N1	0.7029 (3)	0.85534 (18)	0.83254 (13)	0.0228 (5)
C17	0.4542 (3)	0.6665 (2)	0.66382 (16)	0.0202 (5)
C16	0.5244 (3)	0.7123 (2)	0.74765 (16)	0.0185 (5)
C15	0.6344 (3)	0.8138 (2)	0.75010 (16)	0.0198 (5)
C19	0.5908 (3)	0.8185 (2)	0.59116 (16)	0.0208 (5)
C13	0.7824 (3)	0.9642 (2)	0.68483 (17)	0.0257 (6)
H13	0.8111	1.002	0.635	0.031*
C12	0.8496 (3)	1.0043 (2)	0.76748 (17)	0.0283 (6)
H12	0.9256	1.0699	0.7753	0.034*
C14	0.6703 (3)	0.8664 (2)	0.67383 (16)	0.0203 (5)
C11	0.8060 (3)	0.9486 (2)	0.84026 (17)	0.0288 (6)
H11	0.8517	0.9783	0.8973	0.035*
C18	0.4873 (3)	0.7214 (2)	0.58795 (16)	0.0218 (5)
H18	0.436	0.6899	0.5323	0.026*
O3	0.3522 (3)	0.89501 (17)	0.98826 (13)	0.0347 (5)
C3	0.4606 (4)	0.8425 (2)	0.96750 (16)	0.0255 (6)
N3	0.6313 (3)	0.87649 (18)	0.51750 (13)	0.0232 (5)
N4	0.5499 (3)	0.83961 (19)	0.44490 (14)	0.0259 (5)
C21	0.5979 (3)	0.8976 (2)	0.37159 (17)	0.0254 (6)
C22	0.7080 (4)	0.9942 (2)	0.38008 (18)	0.0278 (6)
H22	0.7535	1.0249	0.4369	0.033*
C26	0.5278 (4)	0.8514 (3)	0.28898 (18)	0.0312 (6)
N2	0.8380 (10)	0.6523 (6)	0.8935 (7)	0.0221 (14)	0.707 (12)
C41	0.8099 (8)	0.5457 (6)	0.8581 (5)	0.0290 (14)	0.707 (12)
H41	0.6991	0.5109	0.8539	0.035*	0.707 (12)
C42	0.9356 (7)	0.4839 (6)	0.8274 (4)	0.0415 (15)	0.707 (12)
H42	0.9113	0.4086	0.8021	0.05*	0.707 (12)
C43	1.0977 (7)	0.5344 (7)	0.8342 (4)	0.0455 (19)	0.707 (12)
H43	1.1863	0.4943	0.8134	0.055*	0.707 (12)
C44	1.1279 (8)	0.6420 (7)	0.8711 (7)	0.0471 (18)	0.707 (12)
H44	1.2376	0.6783	0.8752	0.057*	0.707 (12)
C45	0.9984 (10)	0.6985 (7)	0.9027 (7)	0.0344 (13)	0.707 (12)
H45	1.0227	0.7717	0.9316	0.041*	0.707 (12)
C23	0.7519 (4)	1.0460 (3)	0.30661 (19)	0.0324 (7)
H23	0.8268	1.1122	0.3126	0.039*
C24	0.6850 (4)	0.9999 (3)	0.22435 (19)	0.0372 (7)
H24	0.7152	1.0342	0.1734	0.045*
C25	0.5757 (4)	0.9053 (3)	0.21571 (19)	0.0388 (8)
H25	0.531	0.8753	0.1585	0.047*
C27	0.4086 (4)	0.7471 (3)	0.2782 (2)	0.0433 (8)
H27A	0.374	0.728	0.2155	0.065*
H27B	0.3082	0.7629	0.3059	0.065*
H27C	0.4658	0.6825	0.3061	0.065*
N5	0.3525 (3)	0.56333 (19)	0.65987 (15)	0.0265 (5)
N6	0.3185 (3)	0.51923 (19)	0.58235 (15)	0.0281 (5)
C31	0.2099 (3)	0.4182 (2)	0.57341 (19)	0.0274 (6)
C32	0.1780 (4)	0.3545 (2)	0.64501 (19)	0.0315 (6)
H32	0.2352	0.3755	0.7021	0.038*
C36	0.1327 (4)	0.3861 (2)	0.48863 (19)	0.0311 (6)
C37	0.1705 (4)	0.4519 (3)	0.4104 (2)	0.0384 (7)
H37A	0.2934	0.4646	0.4133	0.058*
H37B	0.1173	0.526	0.4111	0.058*
H37C	0.1253	0.4078	0.3562	0.058*
C35	0.0163 (4)	0.2935 (3)	0.4778 (2)	0.0382 (7)
H35	−0.0401	0.2715	0.4207	0.046*
C33	0.0645 (4)	0.2619 (3)	0.6331 (2)	0.0410 (8)
H33	0.043	0.2184	0.6816	0.049*
C34	−0.0189 (4)	0.2325 (3)	0.5489 (2)	0.0467 (9)
H34	−0.1005	0.1701	0.5404	0.056*
N2A	0.849 (3)	0.6298 (16)	0.9029 (19)	0.0221 (14)	0.293 (12)
C41A	0.806 (2)	0.5207 (15)	0.8787 (12)	0.0290 (14)	0.293 (12)
H41A	0.691	0.4945	0.8776	0.035*	0.293 (12)
C42A	0.9203 (17)	0.4436 (14)	0.8550 (11)	0.0415 (15)	0.293 (12)
H42A	0.8862	0.3655	0.8405	0.05*	0.293 (12)
C43A	1.0835 (18)	0.4825 (15)	0.8528 (12)	0.0455 (19)	0.293 (12)
H43A	1.1662	0.4311	0.8391	0.055*	0.293 (12)
C44A	1.126 (2)	0.5956 (16)	0.870 (2)	0.0471 (18)	0.293 (12)
H44A	1.2386	0.6239	0.8685	0.057*	0.293 (12)
C45A	1.006 (3)	0.6690 (18)	0.8911 (19)	0.0344 (13)	0.293 (12)
H45A	1.0341	0.749	0.8974	0.041*	0.293 (12)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Re1	0.01829 (6)	0.02938 (6)	0.01247 (5)	−0.00815 (4)	0.00271 (4)	0.00012 (4)
O4	0.0169 (9)	0.0266 (9)	0.0141 (9)	−0.0073 (7)	0.0030 (7)	0.0005 (7)
C1	0.0198 (14)	0.0298 (14)	0.0182 (13)	0.0006 (11)	0.0021 (11)	−0.0005 (11)
C2	0.0294 (16)	0.0438 (17)	0.0200 (14)	−0.0119 (13)	0.0082 (12)	0.0004 (12)
O1	0.0512 (14)	0.0366 (12)	0.0255 (11)	−0.0010 (10)	0.0141 (10)	0.0097 (9)
O2	0.0351 (13)	0.0762 (16)	0.0247 (11)	−0.0232 (11)	0.0001 (10)	−0.0119 (11)
N1	0.0205 (12)	0.0318 (12)	0.0150 (11)	−0.0104 (9)	0.0024 (9)	−0.0007 (9)
C17	0.0162 (13)	0.0243 (13)	0.0191 (13)	−0.0022 (10)	0.0004 (10)	0.0002 (10)
C16	0.0144 (12)	0.0238 (13)	0.0169 (12)	−0.0020 (10)	0.0019 (10)	0.0004 (10)
C15	0.0148 (13)	0.0293 (14)	0.0148 (12)	−0.0043 (10)	0.0025 (10)	0.0001 (10)
C19	0.0220 (14)	0.0257 (13)	0.0150 (12)	0.0012 (10)	0.0035 (10)	0.0009 (10)
C13	0.0246 (15)	0.0335 (15)	0.0185 (13)	−0.0087 (11)	0.0034 (11)	0.0061 (11)
C12	0.0248 (15)	0.0353 (15)	0.0226 (14)	−0.0166 (12)	0.0012 (11)	0.0028 (12)
C14	0.0170 (13)	0.0276 (13)	0.0158 (12)	−0.0032 (10)	0.0023 (10)	0.0004 (10)
C11	0.0284 (15)	0.0386 (16)	0.0167 (13)	−0.0169 (12)	−0.0001 (11)	−0.0008 (11)
C18	0.0233 (14)	0.0249 (13)	0.0158 (13)	0.0001 (10)	−0.0015 (10)	−0.0020 (10)
O3	0.0451 (13)	0.0367 (12)	0.0243 (11)	0.0090 (10)	0.0100 (9)	0.0009 (9)
C3	0.0340 (16)	0.0294 (14)	0.0117 (12)	−0.0086 (12)	0.0006 (11)	0.0034 (11)
N3	0.0271 (13)	0.0280 (12)	0.0142 (11)	0.0004 (9)	0.0022 (9)	0.0003 (9)
N4	0.0291 (13)	0.0307 (12)	0.0178 (11)	0.0002 (10)	0.0035 (10)	0.0002 (9)
C21	0.0271 (15)	0.0333 (15)	0.0167 (13)	0.0060 (11)	0.0048 (11)	0.0021 (11)
C22	0.0331 (16)	0.0317 (15)	0.0191 (14)	0.0039 (12)	0.0050 (12)	0.0014 (11)
C26	0.0292 (16)	0.0451 (17)	0.0184 (14)	0.0042 (13)	0.0012 (12)	−0.0031 (12)
N2	0.0137 (15)	0.040 (3)	0.013 (3)	0.0018 (19)	−0.0005 (16)	0.006 (3)
C41	0.0204 (16)	0.041 (3)	0.026 (4)	0.001 (2)	0.005 (2)	0.002 (2)
C42	0.036 (2)	0.050 (4)	0.039 (4)	0.009 (2)	0.008 (2)	−0.009 (3)
C43	0.022 (2)	0.074 (5)	0.040 (3)	0.013 (3)	0.005 (2)	−0.015 (3)
C44	0.0171 (17)	0.079 (5)	0.043 (2)	−0.002 (3)	0.0042 (15)	−0.025 (5)
C45	0.0182 (17)	0.059 (4)	0.025 (3)	−0.003 (3)	0.0032 (16)	−0.014 (3)
C23	0.0337 (17)	0.0375 (16)	0.0288 (16)	0.0070 (13)	0.0102 (13)	0.0084 (13)
C24	0.0368 (18)	0.055 (2)	0.0232 (16)	0.0121 (15)	0.0107 (13)	0.0134 (14)
C25	0.0350 (18)	0.067 (2)	0.0141 (14)	0.0097 (16)	0.0015 (12)	−0.0005 (14)
C27	0.0398 (19)	0.062 (2)	0.0241 (16)	−0.0059 (16)	−0.0026 (14)	−0.0119 (15)
N5	0.0240 (13)	0.0303 (12)	0.0239 (12)	−0.0023 (9)	0.0013 (10)	−0.0016 (10)
N6	0.0284 (13)	0.0299 (12)	0.0254 (13)	0.0000 (10)	0.0035 (10)	−0.0033 (10)
C31	0.0249 (15)	0.0246 (14)	0.0322 (16)	−0.0002 (11)	0.0036 (12)	−0.0008 (12)
C32	0.0330 (17)	0.0305 (15)	0.0308 (16)	0.0008 (12)	0.0051 (13)	−0.0017 (12)
C36	0.0306 (16)	0.0304 (15)	0.0321 (16)	0.0067 (12)	0.0046 (13)	−0.0059 (12)
C37	0.045 (2)	0.0413 (18)	0.0291 (17)	0.0068 (14)	0.0051 (14)	−0.0053 (13)
C35	0.0414 (19)	0.0323 (16)	0.0380 (18)	−0.0017 (13)	−0.0013 (15)	−0.0089 (14)
C33	0.045 (2)	0.0314 (16)	0.047 (2)	−0.0039 (14)	0.0104 (16)	0.0004 (14)
C34	0.047 (2)	0.0334 (17)	0.057 (2)	−0.0145 (15)	0.0035 (17)	−0.0062 (16)
N2A	0.0137 (15)	0.040 (3)	0.013 (3)	0.0018 (19)	−0.0005 (16)	0.006 (3)
C41A	0.0204 (16)	0.041 (3)	0.026 (4)	0.001 (2)	0.005 (2)	0.002 (2)
C42A	0.036 (2)	0.050 (4)	0.039 (4)	0.009 (2)	0.008 (2)	−0.009 (3)
C43A	0.022 (2)	0.074 (5)	0.040 (3)	0.013 (3)	0.005 (2)	−0.015 (3)
C44A	0.0171 (17)	0.079 (5)	0.043 (2)	−0.002 (3)	0.0042 (15)	−0.025 (5)
C45A	0.0182 (17)	0.059 (4)	0.025 (3)	−0.003 (3)	0.0032 (16)	−0.014 (3)

Geometric parameters (Å, º)

Re1—C2	1.894 (3)	C42—H42	0.95
Re1—C3	1.919 (3)	C43—C44	1.357 (7)
Re1—C1	1.922 (3)	C43—H43	0.95
Re1—O4	2.1256 (16)	C44—C45	1.383 (6)
Re1—N1	2.163 (2)	C44—H44	0.95
Re1—N2	2.164 (8)	C45—H45	0.95
Re1—N2A	2.334 (19)	C23—C24	1.384 (4)
O4—C16	1.305 (3)	C23—H23	0.95
C1—O1	1.152 (3)	C24—C25	1.370 (4)
C2—O2	1.164 (3)	C24—H24	0.95
N1—C11	1.329 (3)	C25—H25	0.95
N1—C15	1.372 (3)	C27—H27A	0.98
C17—C18	1.405 (3)	C27—H27B	0.98
C17—C16	1.409 (3)	C27—H27C	0.98
C17—N5	1.419 (3)	N5—N6	1.271 (3)
C16—C15	1.442 (3)	N6—C31	1.425 (3)
C15—C14	1.405 (3)	C31—C36	1.393 (4)
C19—C18	1.370 (3)	C31—C32	1.399 (4)
C19—N3	1.411 (3)	C32—C33	1.371 (4)
C19—C14	1.424 (3)	C32—H32	0.95
C13—C12	1.367 (4)	C36—C35	1.385 (4)
C13—C14	1.411 (3)	C36—C37	1.512 (4)
C13—H13	0.95	C37—H37A	0.98
C12—C11	1.395 (4)	C37—H37B	0.98
C12—H12	0.95	C37—H37C	0.98
C11—H11	0.95	C35—C34	1.384 (5)
C18—H18	0.95	C35—H35	0.95
O3—C3	1.155 (3)	C33—C34	1.395 (5)
N3—N4	1.262 (3)	C33—H33	0.95
N4—C21	1.428 (3)	C34—H34	0.95
C21—C22	1.391 (4)	N2A—C41A	1.331 (14)
C21—C26	1.395 (4)	N2A—C45A	1.359 (14)
C22—C23	1.384 (4)	C41A—C42A	1.386 (14)
C22—H22	0.95	C41A—H41A	0.95
C26—C25	1.403 (4)	C42A—C43A	1.366 (14)
C26—C27	1.503 (4)	C42A—H42A	0.95
N2—C41	1.337 (7)	C43A—C44A	1.358 (15)
N2—C45	1.354 (6)	C43A—H43A	0.95
C41—C42	1.386 (6)	C44A—C45A	1.373 (14)
C41—H41	0.95	C44A—H44A	0.95
C42—C43	1.387 (7)	C45A—H45A	0.95
C2—Re1—C3	89.53 (12)	C41—C42—C43	118.6 (5)
C2—Re1—C1	87.41 (11)	C41—C42—H42	120.7
C3—Re1—C1	86.85 (11)	C43—C42—H42	120.7
C2—Re1—O4	170.81 (9)	C44—C43—C42	119.1 (5)
C3—Re1—O4	96.81 (9)	C44—C43—H43	120.5
C1—Re1—O4	99.54 (9)	C42—C43—H43	120.5
C2—Re1—N1	96.44 (10)	C43—C44—C45	119.8 (5)
C3—Re1—N1	95.90 (10)	C43—C44—H44	120.1
C1—Re1—N1	175.27 (9)	C45—C44—H44	120.1
O4—Re1—N1	76.35 (7)	N2—C45—C44	121.9 (5)
C2—Re1—N2	92.1 (3)	N2—C45—H45	119.1
C3—Re1—N2	175.9 (3)	C44—C45—H45	119.1
C1—Re1—N2	97.0 (2)	C24—C23—C22	118.9 (3)
O4—Re1—N2	81.1 (3)	C24—C23—H23	120.6
N1—Re1—N2	80.2 (2)	C22—C23—H23	120.6
C2—Re1—N2A	91.4 (6)	C25—C24—C23	120.6 (3)
C3—Re1—N2A	177.0 (6)	C25—C24—H24	119.7
C1—Re1—N2A	90.3 (6)	C23—C24—H24	119.7
O4—Re1—N2A	82.7 (6)	C24—C25—C26	121.8 (3)
N1—Re1—N2A	86.9 (6)	C24—C25—H25	119.1
N2—Re1—N2A	6.7 (8)	C26—C25—H25	119.1
C16—O4—Re1	115.87 (14)	C26—C27—H27A	109.5
O1—C1—Re1	176.2 (2)	C26—C27—H27B	109.5
O2—C2—Re1	176.3 (2)	H27A—C27—H27B	109.5
C11—N1—C15	118.8 (2)	C26—C27—H27C	109.5
C11—N1—Re1	127.27 (17)	H27A—C27—H27C	109.5
C15—N1—Re1	113.82 (16)	H27B—C27—H27C	109.5
C18—C17—C16	120.4 (2)	N6—N5—C17	112.5 (2)
C18—C17—N5	122.2 (2)	N5—N6—C31	115.1 (2)
C16—C17—N5	117.4 (2)	C36—C31—C32	120.8 (3)
O4—C16—C17	125.0 (2)	C36—C31—N6	116.4 (3)
O4—C16—C15	118.5 (2)	C32—C31—N6	122.8 (2)
C17—C16—C15	116.5 (2)	C33—C32—C31	120.3 (3)
N1—C15—C14	122.1 (2)	C33—C32—H32	119.9
N1—C15—C16	115.2 (2)	C31—C32—H32	119.9
C14—C15—C16	122.7 (2)	C35—C36—C31	118.3 (3)
C18—C19—N3	125.3 (2)	C35—C36—C37	120.5 (3)
C18—C19—C14	119.7 (2)	C31—C36—C37	121.3 (3)
N3—C19—C14	115.0 (2)	C36—C37—H37A	109.5
C12—C13—C14	119.7 (2)	C36—C37—H37B	109.5
C12—C13—H13	120.1	H37A—C37—H37B	109.5
C14—C13—H13	120.1	C36—C37—H37C	109.5
C13—C12—C11	119.7 (2)	H37A—C37—H37C	109.5
C13—C12—H12	120.1	H37B—C37—H37C	109.5
C11—C12—H12	120.1	C34—C35—C36	120.9 (3)
C15—C14—C13	117.4 (2)	C34—C35—H35	119.6
C15—C14—C19	118.1 (2)	C36—C35—H35	119.6
C13—C14—C19	124.5 (2)	C32—C33—C34	119.1 (3)
N1—C11—C12	122.3 (2)	C32—C33—H33	120.4
N1—C11—H11	118.8	C34—C33—H33	120.4
C12—C11—H11	118.8	C35—C34—C33	120.6 (3)
C19—C18—C17	122.5 (2)	C35—C34—H34	119.7
C19—C18—H18	118.7	C33—C34—H34	119.7
C17—C18—H18	118.7	C41A—N2A—C45A	116.9 (15)
O3—C3—Re1	177.4 (2)	C41A—N2A—Re1	118.9 (13)
N4—N3—C19	114.8 (2)	C45A—N2A—Re1	123.1 (12)
N3—N4—C21	113.3 (2)	N2A—C41A—C42A	123.1 (15)
C22—C21—C26	120.9 (3)	N2A—C41A—H41A	118.5
C22—C21—N4	123.2 (2)	C42A—C41A—H41A	118.5
C26—C21—N4	115.9 (2)	C43A—C42A—C41A	118.4 (13)
C23—C22—C21	120.7 (3)	C43A—C42A—H42A	120.8
C23—C22—H22	119.7	C41A—C42A—H42A	120.8
C21—C22—H22	119.7	C44A—C43A—C42A	119.1 (13)
C21—C26—C25	117.1 (3)	C44A—C43A—H43A	120.4
C21—C26—C27	121.9 (3)	C42A—C43A—H43A	120.4
C25—C26—C27	121.0 (3)	C43A—C44A—C45A	120.1 (14)
C41—N2—C45	117.8 (6)	C43A—C44A—H44A	120
C41—N2—Re1	122.4 (5)	C45A—C44A—H44A	120
C45—N2—Re1	119.8 (5)	N2A—C45A—C44A	121.4 (16)
N2—C41—C42	122.7 (6)	N2A—C45A—H45A	119.3
N2—C41—H41	118.6	C44A—C45A—H45A	119.3
C42—C41—H41	118.6
C2—Re1—O4—C16	−34.9 (7)	C19—N3—N4—C21	−178.0 (2)
C3—Re1—O4—C16	98.48 (17)	N3—N4—C21—C22	−7.5 (4)
C1—Re1—O4—C16	−173.59 (17)	N3—N4—C21—C26	172.3 (2)
N1—Re1—O4—C16	4.03 (16)	C26—C21—C22—C23	−0.7 (4)
N2—Re1—O4—C16	−77.9 (3)	N4—C21—C22—C23	179.1 (2)
N2A—Re1—O4—C16	−84.5 (6)	C22—C21—C26—C25	1.1 (4)
C2—Re1—C1—O1	42 (4)	N4—C21—C26—C25	−178.7 (2)
C3—Re1—C1—O1	−48 (4)	C22—C21—C26—C27	180.0 (3)
O4—Re1—C1—O1	−144 (4)	N4—C21—C26—C27	0.2 (4)
N1—Re1—C1—O1	−174 (3)	C2—Re1—N2—C41	147.8 (7)
N2—Re1—C1—O1	133 (4)	C3—Re1—N2—C41	−98 (3)
N2A—Re1—C1—O1	133 (4)	C1—Re1—N2—C41	60.1 (7)
C3—Re1—C2—O2	−140 (4)	O4—Re1—N2—C41	−38.5 (6)
C1—Re1—C2—O2	133 (4)	N1—Re1—N2—C41	−116.0 (7)
O4—Re1—C2—O2	−6 (5)	N2A—Re1—N2—C41	64 (7)
N1—Re1—C2—O2	−44 (4)	C2—Re1—N2—C45	−31.5 (9)
N2—Re1—C2—O2	36 (4)	C3—Re1—N2—C45	82 (4)
N2A—Re1—C2—O2	43 (4)	C1—Re1—N2—C45	−119.1 (8)
C2—Re1—N1—C11	−5.7 (3)	O4—Re1—N2—C45	142.3 (9)
C3—Re1—N1—C11	84.5 (2)	N1—Re1—N2—C45	64.7 (8)
C1—Re1—N1—C11	−150.1 (11)	N2A—Re1—N2—C45	−115 (8)
O4—Re1—N1—C11	−179.9 (2)	C45—N2—C41—C42	−3.0 (12)
N2—Re1—N1—C11	−96.8 (3)	Re1—N2—C41—C42	177.7 (5)
N2A—Re1—N1—C11	−96.7 (6)	N2—C41—C42—C43	0.6 (9)
C2—Re1—N1—C15	170.22 (19)	C41—C42—C43—C44	0.3 (9)
C3—Re1—N1—C15	−99.59 (19)	C42—C43—C44—C45	1.3 (13)
C1—Re1—N1—C15	25.8 (12)	C41—N2—C45—C44	4.7 (16)
O4—Re1—N1—C15	−3.99 (17)	Re1—N2—C45—C44	−176.0 (8)
N2—Re1—N1—C15	79.1 (3)	C43—C44—C45—N2	−3.9 (16)
N2A—Re1—N1—C15	79.2 (6)	C21—C22—C23—C24	−0.3 (4)
Re1—O4—C16—C17	175.27 (19)	C22—C23—C24—C25	0.7 (4)
Re1—O4—C16—C15	−3.5 (3)	C23—C24—C25—C26	−0.2 (5)
C18—C17—C16—O4	179.0 (2)	C21—C26—C25—C24	−0.7 (4)
N5—C17—C16—O4	−1.9 (4)	C27—C26—C25—C24	−179.5 (3)
C18—C17—C16—C15	−2.2 (4)	C18—C17—N5—N6	9.9 (3)
N5—C17—C16—C15	176.9 (2)	C16—C17—N5—N6	−169.2 (2)
C11—N1—C15—C14	0.3 (4)	C17—N5—N6—C31	−177.2 (2)
Re1—N1—C15—C14	−176.01 (19)	N5—N6—C31—C36	162.8 (2)
C11—N1—C15—C16	179.8 (2)	N5—N6—C31—C32	−16.1 (4)
Re1—N1—C15—C16	3.6 (3)	C36—C31—C32—C33	−2.7 (4)
O4—C16—C15—N1	−0.1 (3)	N6—C31—C32—C33	176.1 (3)
C17—C16—C15—N1	−179.0 (2)	C32—C31—C36—C35	3.7 (4)
O4—C16—C15—C14	179.4 (2)	N6—C31—C36—C35	−175.2 (2)
C17—C16—C15—C14	0.6 (4)	C32—C31—C36—C37	−178.0 (3)
C14—C13—C12—C11	−0.3 (4)	N6—C31—C36—C37	3.1 (4)
N1—C15—C14—C13	0.7 (4)	C31—C36—C35—C34	−1.8 (4)
C16—C15—C14—C13	−178.9 (2)	C37—C36—C35—C34	179.9 (3)
N1—C15—C14—C19	−178.8 (2)	C31—C32—C33—C34	−0.2 (5)
C16—C15—C14—C19	1.6 (4)	C36—C35—C34—C33	−1.1 (5)
C12—C13—C14—C15	−0.6 (4)	C32—C33—C34—C35	2.1 (5)
C12—C13—C14—C19	178.9 (3)	C2—Re1—N2A—C41A	143.0 (19)
C18—C19—C14—C15	−2.2 (4)	C3—Re1—N2A—C41A	36 (14)
N3—C19—C14—C15	179.3 (2)	C1—Re1—N2A—C41A	56 (2)
C18—C19—C14—C13	178.3 (3)	O4—Re1—N2A—C41A	−44.0 (19)
N3—C19—C14—C13	−0.1 (4)	N1—Re1—N2A—C41A	−121 (2)
C15—N1—C11—C12	−1.3 (4)	N2—Re1—N2A—C41A	−120 (8)
Re1—N1—C11—C12	174.4 (2)	C2—Re1—N2A—C45A	−49 (2)
C13—C12—C11—N1	1.3 (5)	C3—Re1—N2A—C45A	−156 (11)
N3—C19—C18—C17	178.9 (2)	C1—Re1—N2A—C45A	−137 (2)
C14—C19—C18—C17	0.6 (4)	O4—Re1—N2A—C45A	124 (2)
C16—C17—C18—C19	1.7 (4)	N1—Re1—N2A—C45A	47 (2)
N5—C17—C18—C19	−177.4 (2)	N2—Re1—N2A—C45A	48 (6)
C2—Re1—C3—O3	−87 (5)	C45A—N2A—C41A—C42A	10 (4)
C1—Re1—C3—O3	0 (5)	Re1—N2A—C41A—C42A	178.2 (14)
O4—Re1—C3—O3	100 (5)	N2A—C41A—C42A—C43A	−3 (3)
N1—Re1—C3—O3	18E1 (10)	C41A—C42A—C43A—C44A	−3 (3)
N2—Re1—C3—O3	159 (5)	C42A—C43A—C44A—C45A	1 (4)
N2A—Re1—C3—O3	20 (14)	C41A—N2A—C45A—C44A	−11 (4)
C18—C19—N3—N4	7.3 (4)	Re1—N2A—C45A—C44A	−179 (2)
C14—C19—N3—N4	−174.4 (2)	C43A—C44A—C45A—N2A	6 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12···O2^i	0.95	2.52	3.142 (3)	123
C41—H41···O4	0.95	2.50	2.913 (7)	106
C41—H41···O1^ii	0.95	2.59	3.459 (7)	152
C44—H44···O4^iii	0.95	2.35	3.166 (7)	143

Symmetry codes: (i) −x+2, −y+2, −z+2; (ii) −x+1, −y+1, −z+2; (iii) x+1, y, z.