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

Article abstract of DOI:10.1107/S0108270113027947

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(C ₂₃H₂₁N₄O)(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.

Full text of DOI:10.1107/S0108270113027947

metal-organic compounds
Acta Crystallographica Section C
Crystal Structure
Communications
Lawrance, 2004). It has attracted interest in industrial appli-
cations, 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 depro-
tonated 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, and 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
ISSN 0108-2701
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
Marietjie Schutte-Smith,* Theunis J. Muller, Hendrik G.
Visser and Andreas Roodt
Department of Chemistry, University of the Free State, PO Box 339, Bloemfontein
9300, South Africa
Correspondence e-mail: schuttem@ufs.ac.za
Received 29 August 2013
Accepted 11 October 2013
The ReI centres of two ReI–tricarbonyl complexes, viz. tri-
carbonyl(pyridine-ꢀN){5-[2-(2,4,6-trimethylphenyl)diazen-1-
yl]quinolin-8-olato-ꢀ2N1,O}rhenium(I), [Re(C23H21N4O)(CO)3],
(I), and {5,7-bis[2-(2-methylphenyl)diazen-1-yl]quinolin-8-ol-
ato-ꢀ2N1,O}tricarbonyl(pyridine-ꢀN)rhenium(I), [Re(C28H23-
N6O)(CO)3], (II), are facially surrounded by three carbonyl
ligands, a pyridine ligand and either a 5-[2-(2,4,6-trimethyl-
phenyl)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 struc-
ture of (I) is stabilized by two intermolecular C—Hꢀ ꢀ ꢀO
interactions and that of (II) is stabilized by three inter-
molecular C—Hꢀ ꢀ ꢀO hydrogen-bonding interactions.
Keywords: crystal structure; ReI–tricarbonyl complexes; 5-[2-
(2,4,6-trimethylphenyl)diazen-1-yl]quinolin-8-olate; 5,7-bis[2-
(2-methylphenyl)diazen-1-yl]quinolin-8-olate.
1. 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-trimethyl-
phenyl)diazen-1-yl]-8-hydroxyquinolin-8-ol and 5,7-bis[2-(2-
methylphenyl)diazen-1-yl]quinolin-8-ol are considered prom-
ising (Pretorius, 2011). In this paper, we report the preparation
of 5- and 5,7-substituted quinolin-8-ol ligand systems, 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 (Bernhardt &
metal coordination compound also acts as an electron-trans-
port material and it has been suggested that such abilities arise
from ꢁ–ꢁ 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-trans-
port 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. Basu Baul and co-workers (Basu Baul et al., 2006a,b,
2008a,b) have synthesized relevant tin(IV) complexes, while
Acta Cryst. (2013). C69, 1467–1471
doi:10.1107/S0108270113027947
# 2013 International Union of Crystallography 1467

metal-organic compounds
Table 1
Experimental details.
(I)
(II)
Crystal data
Chemical formula
Mr
[Re(C23H21N4O)(CO)3]
639.67
[Re(C28H23N6O)(CO)3]
729.75
Crystal system, space group
Temperature (K)
Monoclinic, P21/c
100
23.723 (3), 6.7123 (7), 14.8382 (17)
90, 94.178 (4), 90
2356.5 (5)
4
Mo Kꢄ
5.20
Triclinic, P1
100
7.9776 (6), 11.6818 (8), 15.3994 (11)
92.113 (4), 98.130 (3), 92.384 (4)
1418.13 (18)
2
Mo Kꢄ
4.33
˚
a, b, c (A)
ꢄ, ꢅ, ꢆ (ꢃ)
3
˚
V (A )
Z
Radiation type
ꢇ (mmꢁ1
Crystal size (mm)
)
0.50 ꢄ 0.16 ꢄ 0.09
0.28 ꢄ 0.13 ꢄ 0.10
Data collection
Diffractometer
Bruker APEXII CCD area-detector
diffractometer
Bruker APEXII CCD area-detector
diffractometer
Absorption correction
Tmin, Tmax
Multi-scan (SADABS; Bruker, 2008)
0.391, 0.640
30040, 5833, 4678
Multi-scan (SADABS; Bruker, 2008)
0.511, 0.648
21043, 6726, 6014
No. of measured, independent and
observed [I > 2ꢈ(I)] reflections
Rint
0.045
0.669
0.023
0.664
ꢁ1
˚
(sin ꢉ/ꢊ)max (A
)
Refinement
R[F2 > 2ꢈ(F2)], wR(F2), S
No. of reflections
0.031, 0.074, 1.13
5833
319
0
H-atom parameters constrained
0.022, 0.045, 1.09
6726
400
60
H-atom parameters constrained
1.16, ꢁ1.56
No. of parameters
No. of restraints
H-atom treatment
ꢁ3
˚
Áꢋmax, Áꢋmin (e A
)
4.32, ꢁ1.58
Computer programs: APEX2 (Bruker, 2008), SAINT-Plus (Bruker, 2008), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), DIAMOND (Brandenburg & Putz, 2005),
SHELXTL (Sheldrick, 2008) and WinGX (Farrugia, 2012).
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 back-
bone with diazenyl substituents to give 5-[2-(2,4,6-trimethyl-
phenyl)diazen-1-yl]quinolin-8-ol and 5,7-bis[2-(2-methylphenyl)-
diazen-1-yl]quinolin-8-ol. These functionalizations were per-
formed 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.
5,7-Bis[2-(2-methylphenyl)diazen-1-yl]quinolin-8-ol was pre-
pared 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 added slowly 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 slowly acidified
with dilute hydrochloric acid to a pH between 4 and 5 and only
then allowed to reach room temperature; if necessary, the pH
was again adjusted to pH = 4–5. 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): ꢂ 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, ꢃ,
cmꢁ1): 1498 (diazenyl, vs), 1454 (diazenyl, vs).
2. Experimental
2.1. Synthesis and crystallization
5-[2-(2,4,6-Trimethylphenyl)diazen-1-yl]quinolin-8-ol was pre-
pared as described by van Rensburg (2008). Spectroscopic
analysis: 13C NMR (600 MHz, C5D5N): ꢂ 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, ꢃ, cmꢁ1): 1510 (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
ꢂ
1468 Schutte-Smith et al.
[Re(C23H21N4O)(CO)3] and [Re(C28H23N6O)(CO)3]
Acta Cryst. (2013). C69, 1467–1471

metal-organic compounds
mixture was stirred overnight at room temperature. The
precipitate which formed was filtered off, dried and dissolved
in pyridine. The vial was left overnight and brown plate-like
crystals of (I) was obtained by evaporation of the pyridine.
Spectroscopic analysis: 13C NMR (600 MHz, C5D5N): ꢂ 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, ꢃ, cmꢁ1): 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,
Figure 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.
0.0389 mmol) was added to the solution and the mixture was
stirred for 24 h. The red precipitate which formed was dried,
dissolved in pyridine and after evaporation of the solvent, red
cuboidal crystals of (II) were obtained. Spectroscopic analysis:
13C NMR (600 MHz, C5D5N): ꢂ 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,
ꢃ, cmꢁ1): 2022 (CO, vs), 1894 (CO, vs), 1501 (diazenyl, vs),
1449 (diazenyl, vs).
workers (Basu Baul et al., 2006a,b, 2008a,b), which range
between 75.18 (4) and 73.53 (4)ꢃ.
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)ꢃ, 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 80.85ꢃ. Note, however,
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
2.2. 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
˚
1.924 (5) A, and those of (II) between 1.894 (3) and
˚
constrained to ride on their parent atoms, with C—H = 0.95 A
˚
1.922 (3) A. These are well within the range of distances seen
2
and Uiso(H) = 1.2Ueq(C) for sp CH, and with C—H = 0.98 A
˚
for other tricarbonylrhenium(I) structures (Schutte & Visser,
2008; Schutte et al., 2007, 2008, 2009, 2010, 2011, 2012a,b,c).
The Re—O bond lengths for the quinolin-8-ol ligands are
and Uiso(H) = 1.5Ueq(C) for methyl groups. For (I), a large
˚
residual electron-density peak is present less than 1 A 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. Obtaining chemically reasonable geometries
required restraint of the geometry of the minor disorder
component to be similar to that of the major component [site-
occupation factor refined to 0.707 (12)] and imposition of
restraints upon the displacement parameters of the pyridine
ring. This gave a total of 60 restraints.
˚
almost equal at 2.121 (3) and 2.1256 (16) A for (I) and (II),
respectively, while the Re—N bond lengths are also similar at
˚
2.179 (4) and 2.163 (2) A, 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 Basu Baul
3. Results and discussion
In the crystal structures of both tricarbonyl(pyridine-ꢀN){5-[2-
(2,4,6-trimethylphenyl)diazen-1-yl]quinolin-8-olato-ꢀ2N1,O}-
rhenium(I), (I) (Fig. 1), and tricarbonyl(pyridine-ꢀN){5,7-
bis[2-(2-methylphenyl)diazen-1-yl]quinolin-8-olato-ꢀ2N1,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)ꢃ, and C3—Re—N2 angles of
176.50 (18) and 175.9 (3)ꢃ, 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 75.66ꢃ and a carbonyl–Re–N(Py) angle of 178.01ꢃ.
The chelate bite angle also compares well with those of the
diazenylquinolin-8-ol ligands reported by Basu Baul and co-
Figure 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.
ꢂ
Acta Cryst. (2013). C69, 1467–1471
Schutte-Smith et al.
[Re(C23H21N4O)(CO)3] and [Re(C28H23N6O)(CO)3] 1469

metal-organic compounds
Figure 3
A graphical representation of the infinite one-dimensional chains formed
by intermolecular C—Hꢀ ꢀ ꢀO interactions along the [010] vector in the
structure of (I). Generic atoms labels without symmetry codes have been
used. Dashed lines indicate hydrogen bonds.
Figure 4
A graphical representation of the infinite one-dimensional chains formed
by intermolecular C—Hꢀ ꢀ ꢀO interactions along the [100] vector in the
structure of (II). Generic atoms labels without symmetry codes have been
used. Dashed lines indicate hydrogen bonds.
and co-workers (Basu Baul et al., 2006a,b, 2008a,b) differed by
˚
0.2 to 0.3 A.
The diazenyl N N bond lengths of (II) are 1.271 (3) and
well with similar complexes involving tropolone and 2,4-di-
quinoline, where bond lengths of 2.208 (4) (Schutte et al.,
˚
2012b) and 2.203 (4) A were reported (Schutte et al., 2011).
˚
˚
1.262 (3) A, while that of (I) is 1.256 (6) A. These values are
again within the range found for structures reported by Basu
Baul and co-workers (Basu Baul et al., 2006a,b, 2008a,b) and
compare well with similar distances in free ligands.
Two intermolecular C—Hꢀ ꢀ ꢀO interactions are observed in
the crystal structure of (I) (see Table 2). The pyridine ligand
forms C—Hꢀ ꢀ ꢀO interactions with the carbonyl O atoms of
neighbouring molecules. A short C14ꢀ ꢀ ꢀO4i interaction
In (I), the dihedral angle formed between the plane of the
2,4,6-trimethylphenyl ring (C31–C36; r.m.s. deviation =
˚
0.0089 A) and the plane of the oxygen-substituted ring of the
˚
[3.205 (6) A; see Table 2 for full details and symmetry code] is
˚
quinolin-8-olate ligand (C24–C29; r.m.s. deviation = 0.0117 A)
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).
is 2.5 (3)ꢃ. A near coplanar conformation is also seen in (II), as
is shown by the angle between the plane of the (2-methyl-
˚
phenyl)diazenyl ring (C21–C26; r.m.s. deviation = 0.0040 A)
and the oxygen-bearing ring of the quinolin-8-olate ligand
ꢃ
The structure of (II) displays three intermolecular C—
Hꢀ ꢀ ꢀO interactions and one intramolecular C—Hꢀ ꢀ ꢀO inter-
action (Table 3). As atom C41 is part of the disordered pyri-
dine ligand, some care needs to be taken with interpreting the
detail here. However, as with (I), it can be seen that the
˚
(C14–C19, r.m.s. deviation = 0.0103 A) of 3.05 (15) . Mean-
while, the dihedral angle between the planes of the C31–C36
˚
(r.m.s. deviation = 0.0130 A) and C14–C19 rings is slightly
larger, at 6.24 (15)ꢃ. The Re—N(pyridine) bond length is
˚
2.217 (4) A for (I), while the Re—N bond lengths of disor-
˚
dered (II) are 2.164 (8) and 2.334 (19) A. These all compare
Table 3
Hydrogen-bond geometry (A, ) for (II).
ꢃ
˚
D—Hꢀ ꢀ ꢀA
D—H
Hꢀ ꢀ ꢀA
Dꢀ ꢀ ꢀA
D—Hꢀ ꢀ ꢀA
Table 2
Hydrogen-bond geometry (A, ) for (I).
ꢃ
˚
C12—H12ꢀ ꢀ ꢀO2i
C41—H41ꢀ ꢀ ꢀO4
C41—H41ꢀ ꢀ ꢀO1ii
C44—H44ꢀ ꢀ ꢀO4iii
0.95
0.95
0.95
0.95
2.52
2.50
2.59
2.35
3.142 (3)
2.913 (7)
3.459 (7)
3.166 (7)
123
106
152
143
D—Hꢀ ꢀ ꢀA
D—H
Hꢀ ꢀ ꢀA
Dꢀ ꢀ ꢀA
D—Hꢀ ꢀ ꢀA
C14—H14ꢀ ꢀ ꢀO4i
0.95
0.95
2.48
2.49
3.205 (6)
3.139 (6)
133
126
C12—H12ꢀ ꢀ ꢀO1ii
Symmetry codes: (i) ꢁx þ 2; ꢁy þ 2; ꢁz þ 2; (ii) ꢁx þ 1; ꢁy þ 1; ꢁz þ 2; (iii) x þ 1,
Symmetry codes: (i) x; y þ 1; z; (ii) ꢁx þ 1; ꢁy; ꢁz þ 1.
y; z.
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1470 Schutte-Smith et al.
[Re(C23H21N4O)(CO)3] and [Re(C28H23N6O)(CO)3]
Acta Cryst. (2013). C69, 1467–1471

metal-organic compounds
pyridine ligand forms intermolecular C—Hꢀ ꢀ ꢀO interactions
with neighbouring molecules, in this case one with the coor-
dinated O atom of the bidentate ligand and another with a
carbonyl O atom. Lastly, an intermolecular C—Hꢀ ꢀ ꢀO inter-
action is observed between the quinolin-8-olate backbone and
a carbonyl O atom of a neighbouring molecule. Similarly to
(I), the structure of (II) also exhibits a Py-to-chelate inter-
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Leeuwen, P. W. N. M. van, Zuiderveld, M. A., Swennenhuis, B. H. G., Friexa,
Z., Kramer, P. C. J., Groubitz, K., Fraanje, J., Lutz, M. & Spek, A. L. (2003).
J. Am. Chem. Soc. 125, 5523–5539.
Maiti, S. K., Banerjee, S., Mukherjee, A. K., Malik, K. M. A. & Bhattacharyya,
R. (2005). New J. Chem. 29, 554–563.
Pretorius, A. (2011). Master’s dissertation, University of Pretoria, South
Africa.
Rensburg, J. M. van (2008). PhD thesis, University of the Free State, South
Africa.
Sapochak, L. S., Burrows, E. P., Garbuzov, D., Ho, D. M., Forrest, S. R. &
Thompson, M. E. (1996). J. Phys. Chem. 100, 17766–17771.
Schutte, M., Brink, A., Visser, H. G. & Roodt, A. (2012a). Acta Cryst. E68,
m1208–m1209.
and (II) (2022 and 1894 cmꢁ1) 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 cmꢁ1 (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 anti-
bonding orbitals increases and therefore lowers the observed
IR stretching frequencies (Schutte et al., 2011; Schutte et al.,
2012b). However, it is not clear whether (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. Theore-
tically, 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.
Schutte, M., Kemp, G., Visser, H. G. & Roodt, A. (2011). Inorg. Chem. 50,
12486–12498.
The authors express their gratitude to SASOL, PETLabs
Pharmaceuticals, NECSA [affiliated through the Advanced
Metals Initiative (AMI) of the Department of Science and
Technology (DST)] and the University of the Free State
Strategic Academic Initiative (Advanced Biomolecular
Systems) for financial support of this research initiative. This
work is based on research supported in part by the National
Research Foundation of South Africa (UIDs 71836 and
84913).
Schutte, M. & Visser, H. G. (2008). Acta Cryst. E64, m1226–m1227.
Schutte, M., Visser, H. G. & Brink, A. (2009). Acta Cryst. E65, m1575–
m1576.
Schutte, M., Visser, H. G. & Roodt, A. (2008). Acta Cryst. E64, m1610–
m1611.
Schutte, M., Visser, H. G. & Roodt, A. (2010). Acta Cryst. E66, m859–
m860.
Schutte, M., Visser, H. G. & Roodt, A. (2012b). Inorg. Chem. 51, 11996–
12006.
Schutte, M., Visser, H. G. & Roodt, A. (2012c). Acta Cryst. E68, m1359–
m1360.
Schutte, M., Visser, H. G. & Steyl, G. (2007). Acta Cryst. E63, m3195–
m3196.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.
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Gao, S. & Lau, T.-C. (2011). Chem. Commun. 47, 8694–8696.
Supplementary data for this paper are available from the IUCr electronic
archives (Reference: KY3040). Services for accessing these data are
described at the back of the journal.
ꢂ
Acta Cryst. (2013). C69, 1467–1471
Schutte-Smith et al.
[Re(C23H21N4O)(CO)3] and [Re(C28H23N6O)(CO)3] 1471

supplementary materials
supplementary materials
Acta Cryst. (2013). C69, 1467-1471 [doi:10.1107/S0108270113027947]
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
Marietjie Schutte-Smith, Theunis J. Muller, Hendrik G. Visser and Andreas Roodt
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.
(12hmsc1_0ma) Tricarbonyl(pyridine-κN){5-[2-(2,4,6-trimethylphenyl)diazen-1-yl]quinolin-8-olato-
2
κ N1,O}rhenium(I)
Crystal data
[Re(C23H21N4O)(CO)3]
Mr = 639.67
F(000) = 1248
Dx = 1.803 Mg m−3
Mo Kα radiation, λ = 0.71073 Å
Cell parameters from 9930 reflections
θ = 2.6–28.3°
Monoclinic, P21/c
Hall symbol: -P 2ybc
a = 23.723 (3) Å
b = 6.7123 (7) Å
c = 14.8382 (17) Å
β = 94.178 (4)°
V = 2356.5 (5) Å3
Z = 4
µ = 5.20 mm−1
T = 100 K
Plate, brown
0.5 × 0.16 × 0.09 mm
Data collection
Bruker APEXII CCD area-detector
diffractometer
Graphite monochromator
φ and ω scans
5833 independent reflections
4678 reflections with I > 2σ(I)
Rint = 0.045
θ
max = 28.4°, θmin = 1.7°
Absorption correction: multi-scan
(SADABS; Bruker, 2008)
h = −31→31
k = −8→5
T
min = 0.391, Tmax = 0.640
l = −19→19
30040 measured reflections
Acta Cryst. (2013). C69, 1467-1471
sup-1

supplementary materials
Refinement
Refinement on F2
Least-squares matrix: full
R[F2 > 2σ(F2)] = 0.031
wR(F2) = 0.074
Secondary atom site location: difference Fourier
map
Hydrogen site location: inferred from
neighbouring sites
S = 1.13
5833 reflections
319 parameters
0 restraints
Primary atom site location: structure-invariant
direct methods
H-atom parameters constrained
w = 1/[σ2(Fo2) + (0.0122P)2 + 12.6794P]
where P = (Fo2 + 2Fc2)/3
(Δ/σ)max = 0.001
Δρmax = 4.32 e Å−3
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 (Å2)
x
y
z
Uiso*/Ueq
C1
0.5703 (2)
0.6119 (2)
0.6737 (2)
0.60654 (19)
0.629
0.0612 (7)
0.3853 (7)
0.0455 (8)
0.6023 (7)
0.6655
0.6417 (3)
0.7257 (3)
0.7223 (3)
0.5162 (3)
0.5635
0.0230 (10)
0.0245 (10)
0.0264 (10)
0.0239 (10)
0.029*
C2
C3
C15
H15
C14
H14
C13
H13
C12
H12
C11
H11
C21
H21
C22
H22
C23
H23
C24
C29
C28
H28
C27
H27
C26
0.5857 (2)
0.5946
0.7159 (7)
0.8537
0.4444 (3)
0.4418
0.0252 (10)
0.03*
0.5515 (2)
0.5365
0.6280 (7)
0.7038
0.3758 (3)
0.3256
0.0250 (10)
0.03*
0.5399 (2)
0.5161
0.4268 (7)
0.3623
0.3824 (3)
0.3371
0.0253 (10)
0.03*
0.56334 (19)
0.5556
0.3207 (7)
0.1821
0.4558 (3)
0.459
0.0243 (10)
0.029*
0.7312 (2)
0.7168
0.5539 (8)
0.5926
0.6442 (3)
0.6996
0.0267 (10)
0.032*
0.7736 (2)
0.7878
0.6697 (8)
0.7839
0.6091 (4)
0.6411
0.0306 (11)
0.037*
0.7947 (2)
0.8226
0.6188 (8)
0.6994
0.5290 (4)
0.5044
0.0300 (11)
0.036*
0.77447 (19)
0.7940 (2)
0.7721 (2)
0.7859
0.4443 (8)
0.3738 (8)
0.1978 (8)
0.1504
0.4824 (3)
0.4007 (3)
0.3641 (3)
0.3095
0.0259 (10)
0.0288 (11)
0.0286 (11)
0.034*
0.7307 (2)
0.7176
0.0871 (8)
−0.0346
0.1562 (8)
0.4035 (3)
0.3768
0.0274 (11)
0.033*
0.70832 (19)
0.4832 (3)
0.0238 (10)
Acta Cryst. (2013). C69, 1467-1471
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supplementary materials
C25
N3
0.73209 (18)
0.83498 (17)
0.84495 (18)
0.8870 (2)
0.9127 (2)
0.9535 (2)
0.9715
0.3345 (7)
0.4928 (7)
0.4428 (7)
0.5567 (8)
0.7340 (9)
0.8212 (9)
0.94
0.5223 (3)
0.3620 (3)
0.2832 (3)
0.2421 (4)
0.2745 (4)
0.2243 (4)
0.2461
0.0222 (10)
0.0306 (10)
0.0335 (10)
0.0308 (11)
0.0346 (12)
0.0383 (13)
0.046*
N4
C31
C32
C33
H33
C34
C35
H35
C36
C37
H37A
H37C
H37B
C38
H38C
H38A
H38B
C39
H39A
H39B
H39C
N2
0.9688 (2)
0.9418 (2)
0.9511
0.7406 (9)
0.5702 (9)
0.5163
0.1435 (4)
0.1115 (4)
0.0553
0.0340 (12)
0.0337 (12)
0.04*
0.9014 (2)
0.8979 (3)
0.9189
0.4752 (9)
0.8366 (11)
0.962
0.1591 (4)
0.3601 (5)
0.3671
0.0317 (12)
0.059 (2)
0.088*
0.908
0.7501
0.412
0.088*
0.8572
0.8642
0.3568
0.088*
1.0149 (3)
1.0518
0.8377 (10)
0.7976
0.0941 (4)
0.1221
0.0468 (15)
0.07*
1.0111
0.9829
0.0974
0.07*
1.0116
0.7957
0.0307
0.07*
0.8734 (2)
0.8323
0.2880 (10)
0.3049
0.1216 (4)
0.1181
0.0436 (15)
0.065*
0.8841
0.1754
0.1613
0.065*
0.8857
0.2621
0.0611
0.065*
0.59658 (15)
0.71074 (15)
0.53063 (15)
0.59666 (16)
0.69356 (16)
0.66811 (14)
0.636957 (7)
0.4047 (6)
0.3925 (6)
−0.0338 (5)
0.4896 (5)
−0.0630 (6)
0.0642 (5)
0.21790 (3)
0.5228 (3)
0.6026 (3)
0.6480 (2)
0.7805 (3)
0.7758 (3)
0.5216 (2)
0.632607 (12)
0.0196 (8)
0.0235 (9)
0.0311 (8)
0.0344 (9)
0.0373 (9)
0.0250 (7)
0.02021 (6)
N1
O1
O2
O3
O4
Re1
Atomic displacement parameters (Å2)
U11
U22
U33
U12
U13
U23
C1
0.030 (3)
0.025 (2)
0.027 (2)
0.023 (2)
0.029 (2)
0.031 (3)
0.027 (2)
0.025 (2)
0.026 (2)
0.026 (2)
0.026 (2)
0.021 (2)
0.020 (2)
0.026 (2)
0.025 (2)
0.019 (2)
0.020 (2)
0.022 (3)
0.024 (3)
0.022 (3)
0.018 (2)
0.020 (3)
0.023 (3)
0.022 (3)
0.026 (3)
0.031 (3)
0.030 (3)
0.030 (3)
0.037 (3)
0.035 (3)
0.028 (3)
0.026 (3)
0.019 (2)
−0.0005 (19)
−0.0033 (19)
−0.0017 (19)
−0.0019 (18)
−0.0015 (19)
0.0024 (19)
−0.0023 (19)
−0.0039 (18)
−0.001 (2)
−0.007 (2)
−0.005 (2)
0.0021 (19)
0.002 (2)
0.0014 (19)
0.0002 (19)
0.000 (2)
−0.0035 (18)
−0.002 (2)
−0.004 (2)
−0.0049 (19)
0.000 (2)
C2
0.027 (3)
0.029 (3)
0.027 (3)
0.029 (3)
0.024 (2)
0.025 (3)
0.027 (2)
0.027 (3)
0.034 (3)
0.034 (3)
0.027 (3)
0.030 (3)
0.025 (2)
0.028 (3)
0.026 (2)
C3
C15
C14
C13
C12
C11
C21
C22
C23
C24
C29
C28
C27
C26
0.0030 (19)
0.0032 (19)
0.0015 (19)
−0.0022 (19)
0.0027 (19)
0.001 (2)
0.0016 (19)
−0.001 (2)
−0.0027 (19)
−0.004 (2)
−0.008 (2)
−0.001 (2)
0.000 (2)
−0.002 (2)
0.000 (2)
−0.0015 (19)
0.0009 (19)
0.0027 (19)
0.000 (2)
−0.001 (2)
−0.006 (2)
−0.006 (2)
−0.004 (2)
0.005 (2)
0.002 (2)
0.0038 (18)
−0.0031 (18)
Acta Cryst. (2013). C69, 1467-1471
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supplementary materials
C25
N3
0.019 (2)
0.024 (2)
0.026 (2)
0.023 (2)
0.031 (3)
0.040 (3)
0.030 (3)
0.033 (3)
0.025 (3)
0.067 (5)
0.052 (4)
0.039 (3)
0.0198 (18)
0.0191 (19)
0.0307 (19)
0.042 (2)
0.043 (2)
0.0270 (17)
0.02070 (9)
0.025 (3)
0.038 (3)
0.043 (3)
0.038 (3)
0.041 (3)
0.039 (3)
0.041 (3)
0.043 (3)
0.040 (3)
0.058 (5)
0.048 (4)
0.054 (4)
0.019 (2)
0.028 (2)
0.026 (2)
0.027 (2)
0.030 (2)
0.0229 (18)
0.01862 (10)
0.023 (2)
0.030 (2)
0.033 (2)
0.031 (3)
0.032 (3)
0.036 (3)
0.031 (3)
0.025 (3)
0.030 (3)
0.055 (4)
0.041 (3)
0.039 (3)
0.0201 (19)
0.023 (2)
0.037 (2)
0.035 (2)
0.037 (2)
0.0253 (18)
0.02123 (9)
0.0017 (18)
0.0022 (18)
−0.0004 (19)
0.001 (2)
−0.0008 (17)
0.0037 (17)
0.0054 (18)
0.000 (2)
−0.0033 (19)
−0.003 (2)
−0.003 (2)
0.000 (2)
N4
C31
C32
C33
C34
C35
C36
C37
C38
C39
N2
0.000 (2)
0.006 (2)
−0.004 (2)
−0.003 (2)
0.007 (2)
−0.007 (2)
−0.002 (2)
−0.002 (2)
−0.002 (2)
−0.026 (4)
−0.010 (3)
−0.013 (3)
−0.0003 (14)
−0.0005 (16)
−0.0067 (15)
0.0006 (16)
0.0026 (17)
−0.0015 (14)
−0.00015 (7)
0.000 (2)
0.000 (2)
−0.002 (2)
−0.002 (2)
0.026 (4)
−0.001 (2)
−0.001 (2)
−0.027 (4)
0.006 (3)
0.007 (3)
0.013 (3)
−0.016 (3)
−0.0011 (15)
−0.0048 (17)
0.0009 (16)
−0.0090 (16)
0.0012 (17)
−0.0056 (14)
−0.00218 (8)
0.0049 (15)
0.0007 (15)
0.0046 (16)
0.0096 (17)
−0.0088 (17)
0.0032 (14)
0.00101 (6)
N1
O1
O2
O3
O4
Re1
Geometric parameters (Å, º)
C1—O1
1.145 (6)
C27—C26
1.409 (7)
C1—Re1
C2—O2
1.913 (5)
1.151 (6)
1.909 (5)
1.153 (6)
1.924 (5)
1.352 (6)
1.372 (7)
0.95
C27—H27
C26—O4
0.95
1.303 (6)
1.428 (7)
1.384 (6)
1.256 (6)
1.428 (7)
1.406 (8)
1.412 (7)
1.392 (8)
1.509 (8)
1.388 (8)
0.95
C2—Re1
C3—O3
C26—C25
C25—N1
C3—Re1
C15—N2
C15—C14
C15—H15
C14—C13
C14—H14
C13—C12
C13—H13
C12—C11
C12—H12
C11—N2
C11—H11
C21—N1
C21—C22
C21—H21
C22—C23
C22—H22
C23—C24
C23—H23
C24—C29
C24—C25
C29—C28
C29—N3
N3—N4
N4—C31
C31—C32
C31—C36
C32—C33
C32—C37
C33—C34
C33—H33
C34—C35
C34—C38
C35—C36
C35—H35
C36—C39
C37—H37A
C37—H37C
C37—H37B
C38—H38C
C38—H38A
C38—H38B
C39—H39A
C39—H39B
C39—H39C
N2—Re1
1.387 (7)
0.95
1.383 (7)
0.95
1.384 (7)
0.95
1.378 (8)
1.509 (8)
1.386 (7)
0.95
1.347 (6)
0.95
1.322 (6)
1.401 (7)
0.95
1.508 (8)
0.98
0.98
1.366 (7)
0.95
0.98
0.98
1.425 (7)
0.95
0.98
0.98
1.410 (7)
1.412 (7)
1.386 (7)
1.412 (7)
0.98
0.98
0.98
2.217 (4)
Acta Cryst. (2013). C69, 1467-1471
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supplementary materials
C28—C27
C28—H28
1.395 (7)
0.95
N1—Re1
O4—Re1
2.179 (4)
2.121 (3)
O1—C1—Re1
179.3 (5)
178.5 (5)
176.9 (4)
123.1 (4)
118.4
C34—C33—C32
C34—C33—H33
C32—C33—H33
C35—C34—C33
C35—C34—C38
C33—C34—C38
C34—C35—C36
C34—C35—H35
C36—C35—H35
C35—C36—C31
C35—C36—C39
C31—C36—C39
C32—C37—H37A
C32—C37—H37C
122.2 (5)
118.9
O2—C2—Re1
O3—C3—Re1
118.9
N2—C15—C14
N2—C15—H15
C14—C15—H15
C15—C14—C13
C15—C14—H14
C13—C14—H14
C12—C13—C14
C12—C13—H13
C14—C13—H13
C13—C12—C11
C13—C12—H12
C11—C12—H12
N2—C11—C12
N2—C11—H11
C12—C11—H11
N1—C21—C22
N1—C21—H21
C22—C21—H21
C23—C22—C21
C23—C22—H22
C21—C22—H22
C22—C23—C24
C22—C23—H23
C24—C23—H23
C29—C24—C25
C29—C24—C23
C25—C24—C23
C28—C29—C24
C28—C29—N3
C24—C29—N3
C29—C28—C27
C29—C28—H28
C27—C28—H28
C28—C27—C26
C28—C27—H27
C26—C27—H27
O4—C26—C27
O4—C26—C25
C27—C26—C25
N1—C25—C24
N1—C25—C26
C24—C25—C26
N4—N3—C29
118.5 (5)
121.8 (5)
119.7 (5)
121.8 (5)
119.1
118.4
119.5 (5)
120.3
120.3
119.1
118.2 (5)
120.9
119.1 (5)
119.8 (5)
121.1 (5)
109.5
120.9
119.2 (5)
120.4
109.5
120.4
H37A—C37—H37C
C32—C37—H37B
H37A—C37—H37B
H37C—C37—H37B
C34—C38—H38C
C34—C38—H38A
H38C—C38—H38A
C34—C38—H38B
H38C—C38—H38B
H38A—C38—H38B
C36—C39—H39A
C36—C39—H39B
H39A—C39—H39B
C36—C39—H39C
H39A—C39—H39C
H39B—C39—H39C
C11—N2—C15
109.5
123.1 (4)
118.5
109.5
109.5
118.5
109.5
122.1 (5)
119
109.5
109.5
119
109.5
120.1 (5)
119.9
109.5
109.5
119.9
109.5
119.8 (5)
120.1
109.5
109.5
120.1
109.5
118.3 (5)
125.0 (5)
116.7 (4)
119.1 (5)
124.9 (5)
116.0 (5)
123.0 (5)
118.5
109.5
109.5
109.5
116.9 (4)
120.3 (3)
122.7 (3)
119.2 (4)
128.2 (3)
112.0 (3)
114.7 (3)
88.3 (2)
90.2 (2)
87.5 (2)
173.00 (17)
97.13 (16)
94.50 (17)
97.37 (17)
172.29 (17)
97.73 (18)
C11—N2—Re1
C15—N2—Re1
C21—N1—C25
C21—N1—Re1
118.5
C25—N1—Re1
119.8 (5)
120.1
C26—O4—Re1
C2—Re1—C1
120.1
C2—Re1—C3
122.9 (4)
119.9 (4)
117.1 (4)
122.1 (4)
115.3 (4)
122.6 (4)
114.2 (4)
C1—Re1—C3
C2—Re1—O4
C1—Re1—O4
C3—Re1—O4
C2—Re1—N1
C1—Re1—N1
C3—Re1—N1
Acta Cryst. (2013). C69, 1467-1471
sup-5

supplementary materials
N3—N4—C31
116.1 (5)
120.0 (5)
127.3 (5)
112.7 (5)
118.3 (5)
118.1 (5)
123.6 (5)
O4—Re1—N1
C2—Re1—N2
C1—Re1—N2
C3—Re1—N2
O4—Re1—N2
N1—Re1—N2
76.85 (14)
93.34 (17)
92.74 (17)
176.50 (18)
82.00 (13)
81.73 (14)
C32—C31—C36
C32—C31—N4
C36—C31—N4
C33—C32—C31
C33—C32—C37
C31—C32—C37
N2—C15—C14—C13
C15—C14—C13—C12
C14—C13—C12—C11
C13—C12—C11—N2
N1—C21—C22—C23
C21—C22—C23—C24
C22—C23—C24—C29
C22—C23—C24—C25
C25—C24—C29—C28
C23—C24—C29—C28
C25—C24—C29—N3
C23—C24—C29—N3
C24—C29—C28—C27
N3—C29—C28—C27
C29—C28—C27—C26
C28—C27—C26—O4
C28—C27—C26—C25
C29—C24—C25—N1
C23—C24—C25—N1
C29—C24—C25—C26
C23—C24—C25—C26
O4—C26—C25—N1
C27—C26—C25—N1
O4—C26—C25—C24
C27—C26—C25—C24
C28—C29—N3—N4
C24—C29—N3—N4
C29—N3—N4—C31
N3—N4—C31—C32
N3—N4—C31—C36
C36—C31—C32—C33
N4—C31—C32—C33
C36—C31—C32—C37
N4—C31—C32—C37
C31—C32—C33—C34
C37—C32—C33—C34
C32—C33—C34—C35
C32—C33—C34—C38
C33—C34—C35—C36
C38—C34—C35—C36
C34—C35—C36—C31
1.7 (7)
C14—C15—N2—Re1
C22—C21—N1—C25
C22—C21—N1—Re1
C24—C25—N1—C21
C26—C25—N1—C21
C24—C25—N1—Re1
C26—C25—N1—Re1
C27—C26—O4—Re1
C25—C26—O4—Re1
O2—C2—Re1—C1
O2—C2—Re1—C3
O2—C2—Re1—O4
O2—C2—Re1—N1
O2—C2—Re1—N2
O1—C1—Re1—C2
O1—C1—Re1—C3
O1—C1—Re1—O4
O1—C1—Re1—N1
O1—C1—Re1—N2
O3—C3—Re1—C2
O3—C3—Re1—C1
O3—C3—Re1—O4
O3—C3—Re1—N1
O3—C3—Re1—N2
C26—O4—Re1—C2
C26—O4—Re1—C1
C26—O4—Re1—C3
C26—O4—Re1—N1
C26—O4—Re1—N2
C21—N1—Re1—C2
C25—N1—Re1—C2
C21—N1—Re1—C1
C25—N1—Re1—C1
C21—N1—Re1—C3
C25—N1—Re1—C3
C21—N1—Re1—O4
C25—N1—Re1—O4
C21—N1—Re1—N2
C25—N1—Re1—N2
C11—N2—Re1—C2
C15—N2—Re1—C2
174.2 (3)
0.6 (7)
−0.3 (7)
−1.1 (7)
1.2 (7)
−169.6 (4)
−1.1 (7)
178.7 (4)
170.6 (4)
−9.6 (5)
−173.9 (4)
6.8 (5)
0.8 (8)
−1.8 (8)
−178.1 (5)
1.2 (7)
−1.6 (7)
177.8 (5)
177.9 (4)
−2.8 (7)
0.9 (8)
−114 (17)
159 (17)
27 (17)
61 (17)
−178.5 (5)
1.6 (8)
−21 (17)
−8E1 (4)
1E1 (4)
177.4 (4)
−3.3 (7)
179.6 (4)
0.2 (7)
10E1 (4)
14E1 (4)
−18E1 (10)
94 (8)
−0.2 (7)
−179.6 (4)
2.2 (6)
6 (8)
−91 (8)
−177.2 (4)
−178.0 (4)
2.7 (7)
−168 (8)
−87 (9)
25.8 (15)
166.2 (3)
−105.8 (3)
−8.9 (3)
74.4 (3)
4.5 (4)
9.9 (7)
−169.5 (4)
−178.8 (4)
−9.5 (8)
171.8 (5)
−2.1 (8)
179.3 (5)
177.0 (6)
−1.6 (9)
0.9 (9)
−166.2 (3)
141.4 (12)
−29.4 (15)
−86.6 (4)
102.6 (3)
−179.5 (4)
9.7 (3)
−178.3 (6)
1.1 (9)
−177.6 (5)
−2.0 (8)
176.7 (5)
0.8 (8)
96.9 (4)
−73.9 (3)
−130.1 (4)
54.2 (4)
Acta Cryst. (2013). C69, 1467-1471
sup-6

supplementary materials
C34—C35—C36—C39
C32—C31—C36—C35
N4—C31—C36—C35
C32—C31—C36—C39
N4—C31—C36—C39
C12—C11—N2—C15
C12—C11—N2—Re1
C14—C15—N2—C11
−179.5 (5)
1.2 (8)
C11—N2—Re1—C1
−41.6 (4)
142.7 (4)
52 (3)
C15—N2—Re1—C1
C11—N2—Re1—C3
C15—N2—Re1—C3
C11—N2—Re1—O4
C15—N2—Re1—O4
C11—N2—Re1—N1
C15—N2—Re1—N1
−180.0 (5)
−178.5 (5)
0.3 (7)
−124 (3)
55.2 (3)
0.2 (7)
−120.5 (4)
133.0 (3)
−42.7 (3)
−175.7 (4)
−1.7 (7)
Hydrogen-bond geometry (Å, º)
D—H···A
D—H
H···A
D···A
D—H···A
C14—H14···O4i
C12—H12···O1ii
0.95
0.95
2.48
2.49
3.205 (6)
3.139 (6)
133
126
Symmetry codes: (i) x, y+1, z; (ii) −x+1, −y, −z+1.
2
(10lmsc12_0m) {5,7-Bis[2-(2-methylphenyl)diazen-1-yl]quinolin-8-olato-κ N1,O}tricarbonyl(pyridine-
κN)rhenium(I)
Crystal data
[Re(C28H23N6O)(CO)3]
Mr = 729.75
Triclinic, P1
Z = 2
F(000) = 716
Dx = 1.709 Mg m−3
Mo Kα radiation, λ = 0.71073 Å
Cell parameters from 9973 reflections
θ = 2.7–28.0°
µ = 4.33 mm−1
T = 100 K
Cuboid, red
0.28 × 0.13 × 0.1 mm
Hall symbol: -P 1
a = 7.9776 (6) Å
b = 11.6818 (8) Å
c = 15.3994 (11) Å
α = 92.113 (4)°
β = 98.130 (3)°
γ = 92.384 (4)°
V = 1418.13 (18) Å3
Data collection
Bruker APEXII CCD area-detector
diffractometer
Graphite monochromator
φ and ω scans
6726 independent reflections
6014 reflections with I > 2σ(I)
Rint = 0.023
θ
max = 28.2°, θmin = 3.2°
Absorption correction: multi-scan
(SADABS; Bruker, 2008)
h = −10→10
k = −15→13
l = −20→19
T
min = 0.511, Tmax = 0.648
21043 measured reflections
Refinement
Refinement on F2
Least-squares matrix: full
R[F2 > 2σ(F2)] = 0.022
wR(F2) = 0.045
Secondary atom site location: difference Fourier
map
Hydrogen site location: inferred from
neighbouring sites
S = 1.09
6726 reflections
400 parameters
60 restraints
Primary atom site location: structure-invariant
direct methods
H-atom parameters constrained
w = 1/[σ2(Fo2) + (0.0155P)2 + 0.9052P]
where P = (Fo2 + 2Fc2)/3
(Δ/σ)max = 0.002
Δρmax = 1.16 e Å−3
Δρmin = −1.56 e Å−3
Acta Cryst. (2013). C69, 1467-1471
sup-7

supplementary materials
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 (Å2)
x
y
z
Uiso*/Ueq
Occ. (<1)
Re1
O4
0.638666 (13)
0.4992 (2)
0.5792 (3)
0.7909 (4)
0.5437 (3)
0.8910 (3)
0.7029 (3)
0.4542 (3)
0.5244 (3)
0.6344 (3)
0.5908 (3)
0.7824 (3)
0.8111
0.750241 (9)
0.66867 (14)
0.6463 (2)
0.8267 (3)
0.58915 (17)
0.8737 (2)
0.85534 (18)
0.6665 (2)
0.7123 (2)
0.8138 (2)
0.8185 (2)
0.9642 (2)
1.002
0.936888 (6)
0.82177 (11)
1.02272 (17)
1.02828 (18)
1.07734 (13)
1.08141 (13)
0.83254 (13)
0.66382 (16)
0.74765 (16)
0.75010 (16)
0.59116 (16)
0.68483 (17)
0.635
0.02028 (4)
0.0193 (4)
0.0227 (6)
0.0310 (7)
0.0368 (5)
0.0468 (6)
0.0228 (5)
0.0202 (5)
0.0185 (5)
0.0198 (5)
0.0208 (5)
0.0257 (6)
0.031*
C1
C2
O1
O2
N1
C17
C16
C15
C19
C13
H13
C12
H12
C14
C11
H11
C18
H18
O3
0.8496 (3)
0.9256
1.0043 (2)
1.0699
0.76748 (17)
0.7753
0.0283 (6)
0.034*
0.6703 (3)
0.8060 (3)
0.8517
0.8664 (2)
0.9486 (2)
0.9783
0.67383 (16)
0.84026 (17)
0.8973
0.0203 (5)
0.0288 (6)
0.035*
0.4873 (3)
0.436
0.7214 (2)
0.6899
0.58795 (16)
0.5323
0.0218 (5)
0.026*
0.3522 (3)
0.4606 (4)
0.6313 (3)
0.5499 (3)
0.5979 (3)
0.7080 (4)
0.7535
0.89501 (17)
0.8425 (2)
0.87649 (18)
0.83961 (19)
0.8976 (2)
0.9942 (2)
1.0249
0.98826 (13)
0.96750 (16)
0.51750 (13)
0.44490 (14)
0.37159 (17)
0.38008 (18)
0.4369
0.0347 (5)
0.0255 (6)
0.0232 (5)
0.0259 (5)
0.0254 (6)
0.0278 (6)
0.033*
C3
N3
N4
C21
C22
H22
C26
N2
0.5278 (4)
0.8380 (10)
0.8099 (8)
0.6991
0.8514 (3)
0.6523 (6)
0.5457 (6)
0.5109
0.28898 (18)
0.8935 (7)
0.8581 (5)
0.8539
0.0312 (6)
0.0221 (14)
0.0290 (14)
0.035*
0.707 (12)
0.707 (12)
0.707 (12)
0.707 (12)
0.707 (12)
0.707 (12)
0.707 (12)
C41
H41
C42
H42
C43
H43
0.9356 (7)
0.9113
0.4839 (6)
0.4086
0.8274 (4)
0.8021
0.0415 (15)
0.05*
1.0977 (7)
1.1863
0.5344 (7)
0.4943
0.8342 (4)
0.8134
0.0455 (19)
0.055*
Acta Cryst. (2013). C69, 1467-1471
sup-8

supplementary materials
C44
1.1279 (8)
1.2376
0.6420 (7)
0.6783
0.8711 (7)
0.8752
0.0471 (18)
0.057*
0.707 (12)
0.707 (12)
0.707 (12)
0.707 (12)
H44
C45
0.9984 (10)
1.0227
0.6985 (7)
0.7717
0.9027 (7)
0.9316
0.0344 (13)
0.041*
H45
C23
0.7519 (4)
0.8268
1.0460 (3)
1.1122
0.30661 (19)
0.3126
0.0324 (7)
0.039*
H23
C24
0.6850 (4)
0.7152
0.9999 (3)
1.0342
0.22435 (19)
0.1734
0.0372 (7)
0.045*
H24
C25
0.5757 (4)
0.531
0.9053 (3)
0.8753
0.21571 (19)
0.1585
0.0388 (8)
0.047*
H25
C27
0.4086 (4)
0.374
0.7471 (3)
0.728
0.2782 (2)
0.2155
0.0433 (8)
0.065*
H27A
H27B
H27C
N5
0.3082
0.7629
0.3059
0.065*
0.4658
0.6825
0.3061
0.065*
0.3525 (3)
0.3185 (3)
0.2099 (3)
0.1780 (4)
0.2352
0.56333 (19)
0.51923 (19)
0.4182 (2)
0.3545 (2)
0.3755
0.65987 (15)
0.58235 (15)
0.57341 (19)
0.64501 (19)
0.7021
0.0265 (5)
0.0281 (5)
0.0274 (6)
0.0315 (6)
0.038*
N6
C31
C32
H32
C36
0.1327 (4)
0.1705 (4)
0.2934
0.3861 (2)
0.4519 (3)
0.4646
0.48863 (19)
0.4104 (2)
0.4133
0.0311 (6)
0.0384 (7)
0.058*
C37
H37A
H37B
H37C
C35
0.1173
0.526
0.4111
0.058*
0.1253
0.4078
0.3562
0.058*
0.0163 (4)
−0.0401
0.0645 (4)
0.043
0.2935 (3)
0.2715
0.4778 (2)
0.4207
0.0382 (7)
0.046*
H35
C33
0.2619 (3)
0.2184
0.6331 (2)
0.6816
0.0410 (8)
0.049*
H33
C34
−0.0189 (4)
−0.1005
0.849 (3)
0.806 (2)
0.691
0.2325 (3)
0.1701
0.5489 (2)
0.5404
0.0467 (9)
0.056*
H34
N2A
C41A
H41A
C42A
H42A
C43A
H43A
C44A
H44A
C45A
H45A
0.6298 (16)
0.5207 (15)
0.4945
0.9029 (19)
0.8787 (12)
0.8776
0.0221 (14)
0.0290 (14)
0.035*
0.293 (12)
0.293 (12)
0.293 (12)
0.293 (12)
0.293 (12)
0.293 (12)
0.293 (12)
0.293 (12)
0.293 (12)
0.293 (12)
0.293 (12)
0.9203 (17)
0.8862
0.4436 (14)
0.3655
0.8550 (11)
0.8405
0.0415 (15)
0.05*
1.0835 (18)
1.1662
0.4825 (15)
0.4311
0.8528 (12)
0.8391
0.0455 (19)
0.055*
1.126 (2)
1.2386
0.5956 (16)
0.6239
0.870 (2)
0.8685
0.0471 (18)
0.057*
1.006 (3)
1.0341
0.6690 (18)
0.749
0.8911 (19)
0.8974
0.0344 (13)
0.041*
Atomic displacement parameters (Å2)
U11
U22
U33
U12
U13
U23
Re1
O4
C1
0.01829 (6)
0.0169 (9)
0.0198 (14)
0.0294 (16)
0.02938 (6)
0.0266 (9)
0.0298 (14)
0.0438 (17)
0.01247 (5)
0.0141 (9)
0.0182 (13)
0.0200 (14)
−0.00815 (4)
0.00271 (4)
0.0030 (7)
0.0021 (11)
0.0082 (12)
0.00012 (4)
0.0005 (7)
−0.0073 (7)
0.0006 (11)
−0.0119 (13)
−0.0005 (11)
0.0004 (12)
C2
Acta Cryst. (2013). C69, 1467-1471
sup-9

supplementary materials
O1
0.0512 (14)
0.0351 (13)
0.0205 (12)
0.0162 (13)
0.0144 (12)
0.0148 (13)
0.0220 (14)
0.0246 (15)
0.0248 (15)
0.0170 (13)
0.0284 (15)
0.0233 (14)
0.0451 (13)
0.0340 (16)
0.0271 (13)
0.0291 (13)
0.0271 (15)
0.0331 (16)
0.0292 (16)
0.0137 (15)
0.0204 (16)
0.036 (2)
0.0366 (12)
0.0762 (16)
0.0318 (12)
0.0243 (13)
0.0238 (13)
0.0293 (14)
0.0257 (13)
0.0335 (15)
0.0353 (15)
0.0276 (13)
0.0386 (16)
0.0249 (13)
0.0367 (12)
0.0294 (14)
0.0280 (12)
0.0307 (12)
0.0333 (15)
0.0317 (15)
0.0451 (17)
0.040 (3)
0.0255 (11)
0.0247 (11)
0.0150 (11)
0.0191 (13)
0.0169 (12)
0.0148 (12)
0.0150 (12)
0.0185 (13)
0.0226 (14)
0.0158 (12)
0.0167 (13)
0.0158 (13)
0.0243 (11)
0.0117 (12)
0.0142 (11)
0.0178 (11)
0.0167 (13)
0.0191 (14)
0.0184 (14)
0.013 (3)
−0.0010 (10)
−0.0232 (11)
−0.0104 (9)
−0.0022 (10)
−0.0020 (10)
−0.0043 (10)
0.0012 (10)
−0.0087 (11)
−0.0166 (12)
−0.0032 (10)
−0.0169 (12)
0.0001 (10)
0.0090 (10)
−0.0086 (12)
0.0004 (9)
0.0141 (10)
0.0001 (10)
0.0024 (9)
0.0004 (10)
0.0019 (10)
0.0025 (10)
0.0035 (10)
0.0034 (11)
0.0012 (11)
0.0023 (10)
−0.0001 (11)
−0.0015 (10)
0.0100 (9)
0.0006 (11)
0.0022 (9)
0.0035 (10)
0.0048 (11)
0.0050 (12)
0.0012 (12)
−0.0005 (16)
0.005 (2)
0.0097 (9)
O2
−0.0119 (11)
−0.0007 (9)
0.0002 (10)
0.0004 (10)
0.0001 (10)
0.0009 (10)
0.0061 (11)
0.0028 (12)
0.0004 (10)
−0.0008 (11)
−0.0020 (10)
0.0009 (9)
N1
C17
C16
C15
C19
C13
C12
C14
C11
C18
O3
C3
0.0034 (11)
0.0003 (9)
N3
N4
0.0002 (10)
0.0060 (11)
0.0039 (12)
0.0042 (13)
0.0018 (19)
0.001 (2)
0.0002 (9)
C21
C22
C26
N2
0.0021 (11)
0.0014 (11)
−0.0031 (12)
0.006 (3)
C41
C42
C43
C44
C45
C23
C24
C25
C27
N5
0.041 (3)
0.026 (4)
0.002 (2)
0.050 (4)
0.039 (4)
0.009 (2)
0.008 (2)
−0.009 (3)
−0.015 (3)
−0.025 (5)
−0.014 (3)
0.0084 (13)
0.0134 (14)
−0.0005 (14)
−0.0119 (15)
−0.0016 (10)
−0.0033 (10)
−0.0008 (12)
−0.0017 (12)
−0.0059 (12)
−0.0053 (13)
−0.0089 (14)
0.0004 (14)
−0.0062 (16)
0.006 (3)
0.022 (2)
0.074 (5)
0.040 (3)
0.013 (3)
0.005 (2)
0.0171 (17)
0.0182 (17)
0.0337 (17)
0.0368 (18)
0.0350 (18)
0.0398 (19)
0.0240 (13)
0.0284 (13)
0.0249 (15)
0.0330 (17)
0.0306 (16)
0.045 (2)
0.079 (5)
0.043 (2)
−0.002 (3)
0.0042 (15)
0.0032 (16)
0.0102 (13)
0.0107 (13)
0.0015 (12)
−0.0026 (14)
0.0013 (10)
0.0035 (10)
0.0036 (12)
0.0051 (13)
0.0046 (13)
0.0051 (14)
−0.0013 (15)
0.0104 (16)
0.0035 (17)
−0.0005 (16)
0.005 (2)
0.059 (4)
0.025 (3)
−0.003 (3)
0.0375 (16)
0.055 (2)
0.0288 (16)
0.0232 (16)
0.0141 (14)
0.0241 (16)
0.0239 (12)
0.0254 (13)
0.0322 (16)
0.0308 (16)
0.0321 (16)
0.0291 (17)
0.0380 (18)
0.047 (2)
0.0070 (13)
0.0121 (15)
0.0097 (16)
−0.0059 (16)
−0.0023 (9)
0.0000 (10)
−0.0002 (11)
0.0008 (12)
0.0067 (12)
0.0068 (14)
−0.0017 (13)
−0.0039 (14)
−0.0145 (15)
0.0018 (19)
0.001 (2)
0.067 (2)
0.062 (2)
0.0303 (12)
0.0299 (12)
0.0246 (14)
0.0305 (15)
0.0304 (15)
0.0413 (18)
0.0323 (16)
0.0314 (16)
0.0334 (17)
0.040 (3)
N6
C31
C32
C36
C37
C35
C33
C34
N2A
C41A
C42A
C43A
C44A
C45A
0.0414 (19)
0.045 (2)
0.047 (2)
0.057 (2)
0.0137 (15)
0.0204 (16)
0.036 (2)
0.013 (3)
0.041 (3)
0.026 (4)
0.002 (2)
0.050 (4)
0.039 (4)
0.009 (2)
0.008 (2)
−0.009 (3)
−0.015 (3)
−0.025 (5)
−0.014 (3)
0.022 (2)
0.074 (5)
0.040 (3)
0.013 (3)
0.005 (2)
0.0171 (17)
0.0182 (17)
0.079 (5)
0.043 (2)
−0.002 (3)
0.0042 (15)
0.0032 (16)
0.059 (4)
0.025 (3)
−0.003 (3)
Geometric parameters (Å, º)
Re1—C2
Re1—C3
Re1—C1
1.894 (3)
C42—H42
0.95
1.919 (3)
1.922 (3)
C43—C44
C43—H43
1.357 (7)
0.95
Acta Cryst. (2013). C69, 1467-1471
sup-10

supplementary materials
Re1—O4
Re1—N1
Re1—N2
Re1—N2A
O4—C16
C1—O1
2.1256 (16)
2.163 (2)
2.164 (8)
2.334 (19)
1.305 (3)
1.152 (3)
1.164 (3)
1.329 (3)
1.372 (3)
1.405 (3)
1.409 (3)
1.419 (3)
1.442 (3)
1.405 (3)
1.370 (3)
1.411 (3)
1.424 (3)
1.367 (4)
1.411 (3)
0.95
C44—C45
1.383 (6)
0.95
C44—H44
C45—H45
0.95
C23—C24
1.384 (4)
0.95
C23—H23
C24—C25
1.370 (4)
0.95
C2—O2
C24—H24
N1—C11
N1—C15
C17—C18
C17—C16
C17—N5
C16—C15
C15—C14
C19—C18
C19—N3
C19—C14
C13—C12
C13—C14
C13—H13
C12—C11
C12—H12
C11—H11
C18—H18
O3—C3
C25—H25
0.95
C27—H27A
C27—H27B
C27—H27C
N5—N6
0.98
0.98
0.98
1.271 (3)
1.425 (3)
1.393 (4)
1.399 (4)
1.371 (4)
0.95
N6—C31
C31—C36
C31—C32
C32—C33
C32—H32
C36—C35
1.385 (4)
1.512 (4)
0.98
C36—C37
C37—H37A
C37—H37B
C37—H37C
C35—C34
1.395 (4)
0.95
0.98
0.98
0.95
1.384 (5)
0.95
0.95
C35—H35
C33—C34
1.155 (3)
1.262 (3)
1.428 (3)
1.391 (4)
1.395 (4)
1.384 (4)
0.95
1.395 (5)
0.95
N3—N4
C33—H33
N4—C21
C21—C22
C21—C26
C22—C23
C22—H22
C26—C25
C26—C27
N2—C41
N2—C45
C41—C42
C41—H41
C42—C43
C34—H34
0.95
N2A—C41A
N2A—C45A
C41A—C42A
C41A—H41A
C42A—C43A
C42A—H42A
C43A—C44A
C43A—H43A
C44A—C45A
C44A—H44A
C45A—H45A
1.331 (14)
1.359 (14)
1.386 (14)
0.95
1.403 (4)
1.503 (4)
1.337 (7)
1.354 (6)
1.386 (6)
0.95
1.366 (14)
0.95
1.358 (15)
0.95
1.373 (14)
0.95
1.387 (7)
0.95
C2—Re1—C3
C2—Re1—C1
C3—Re1—C1
C2—Re1—O4
C3—Re1—O4
C1—Re1—O4
C2—Re1—N1
C3—Re1—N1
C1—Re1—N1
O4—Re1—N1
89.53 (12)
87.41 (11)
86.85 (11)
170.81 (9)
96.81 (9)
99.54 (9)
96.44 (10)
95.90 (10)
175.27 (9)
76.35 (7)
C41—C42—C43
C41—C42—H42
C43—C42—H42
C44—C43—C42
C44—C43—H43
C42—C43—H43
C43—C44—C45
C43—C44—H44
C45—C44—H44
N2—C45—C44
118.6 (5)
120.7
120.7
119.1 (5)
120.5
120.5
119.8 (5)
120.1
120.1
121.9 (5)
Acta Cryst. (2013). C69, 1467-1471
sup-11

supplementary materials
C2—Re1—N2
92.1 (3)
175.9 (3)
97.0 (2)
81.1 (3)
80.2 (2)
91.4 (6)
177.0 (6)
90.3 (6)
82.7 (6)
86.9 (6)
6.7 (8)
N2—C45—H45
C44—C45—H45
C24—C23—C22
C24—C23—H23
C22—C23—H23
C25—C24—C23
C25—C24—H24
C23—C24—H24
C24—C25—C26
C24—C25—H25
C26—C25—H25
C26—C27—H27A
C26—C27—H27B
119.1
C3—Re1—N2
119.1
C1—Re1—N2
118.9 (3)
120.6
O4—Re1—N2
N1—Re1—N2
C2—Re1—N2A
C3—Re1—N2A
C1—Re1—N2A
O4—Re1—N2A
N1—Re1—N2A
N2—Re1—N2A
C16—O4—Re1
O1—C1—Re1
120.6
120.6 (3)
119.7
119.7
121.8 (3)
119.1
119.1
115.87 (14)
176.2 (2)
176.3 (2)
118.8 (2)
127.27 (17)
113.82 (16)
120.4 (2)
122.2 (2)
117.4 (2)
125.0 (2)
118.5 (2)
116.5 (2)
122.1 (2)
115.2 (2)
122.7 (2)
125.3 (2)
119.7 (2)
115.0 (2)
119.7 (2)
120.1
109.5
109.5
O2—C2—Re1
H27A—C27—H27B
C26—C27—H27C
H27A—C27—H27C
H27B—C27—H27C
N6—N5—C17
109.5
C11—N1—C15
C11—N1—Re1
C15—N1—Re1
C18—C17—C16
C18—C17—N5
C16—C17—N5
O4—C16—C17
O4—C16—C15
C17—C16—C15
N1—C15—C14
N1—C15—C16
C14—C15—C16
C18—C19—N3
C18—C19—C14
N3—C19—C14
C12—C13—C14
C12—C13—H13
C14—C13—H13
C13—C12—C11
C13—C12—H12
C11—C12—H12
C15—C14—C13
C15—C14—C19
C13—C14—C19
N1—C11—C12
N1—C11—H11
C12—C11—H11
C19—C18—C17
C19—C18—H18
C17—C18—H18
O3—C3—Re1
109.5
109.5
109.5
112.5 (2)
115.1 (2)
120.8 (3)
116.4 (3)
122.8 (2)
120.3 (3)
119.9
N5—N6—C31
C36—C31—C32
C36—C31—N6
C32—C31—N6
C33—C32—C31
C33—C32—H32
C31—C32—H32
C35—C36—C31
C35—C36—C37
C31—C36—C37
C36—C37—H37A
C36—C37—H37B
H37A—C37—H37B
C36—C37—H37C
H37A—C37—H37C
H37B—C37—H37C
C34—C35—C36
C34—C35—H35
C36—C35—H35
C32—C33—C34
C32—C33—H33
C34—C33—H33
C35—C34—C33
C35—C34—H34
C33—C34—H34
C41A—N2A—C45A
C41A—N2A—Re1
C45A—N2A—Re1
N2A—C41A—C42A
N2A—C41A—H41A
C42A—C41A—H41A
119.9
118.3 (3)
120.5 (3)
121.3 (3)
109.5
109.5
109.5
120.1
109.5
119.7 (2)
120.1
109.5
109.5
120.1
120.9 (3)
119.6
117.4 (2)
118.1 (2)
124.5 (2)
122.3 (2)
118.8
119.6
119.1 (3)
120.4
120.4
118.8
120.6 (3)
119.7
122.5 (2)
118.7
119.7
118.7
116.9 (15)
118.9 (13)
123.1 (12)
123.1 (15)
118.5
177.4 (2)
114.8 (2)
113.3 (2)
120.9 (3)
123.2 (2)
N4—N3—C19
N3—N4—C21
C22—C21—C26
C22—C21—N4
118.5
Acta Cryst. (2013). C69, 1467-1471
sup-12

supplementary materials
C26—C21—N4
C23—C22—C21
C23—C22—H22
C21—C22—H22
C21—C26—C25
C21—C26—C27
C25—C26—C27
C41—N2—C45
C41—N2—Re1
C45—N2—Re1
N2—C41—C42
N2—C41—H41
C42—C41—H41
115.9 (2)
120.7 (3)
119.7
C43A—C42A—C41A
118.4 (13)
120.8
C43A—C42A—H42A
C41A—C42A—H42A
C44A—C43A—C42A
C44A—C43A—H43A
C42A—C43A—H43A
C43A—C44A—C45A
C43A—C44A—H44A
C45A—C44A—H44A
N2A—C45A—C44A
N2A—C45A—H45A
C44A—C45A—H45A
120.8
119.7
119.1 (13)
120.4
117.1 (3)
121.9 (3)
121.0 (3)
117.8 (6)
122.4 (5)
119.8 (5)
122.7 (6)
118.6
120.4
120.1 (14)
120
120
121.4 (16)
119.3
119.3
118.6
C2—Re1—O4—C16
C3—Re1—O4—C16
C1—Re1—O4—C16
N1—Re1—O4—C16
N2—Re1—O4—C16
N2A—Re1—O4—C16
C2—Re1—C1—O1
C3—Re1—C1—O1
O4—Re1—C1—O1
N1—Re1—C1—O1
N2—Re1—C1—O1
N2A—Re1—C1—O1
C3—Re1—C2—O2
C1—Re1—C2—O2
O4—Re1—C2—O2
N1—Re1—C2—O2
N2—Re1—C2—O2
N2A—Re1—C2—O2
C2—Re1—N1—C11
C3—Re1—N1—C11
C1—Re1—N1—C11
O4—Re1—N1—C11
N2—Re1—N1—C11
N2A—Re1—N1—C11
C2—Re1—N1—C15
C3—Re1—N1—C15
C1—Re1—N1—C15
O4—Re1—N1—C15
N2—Re1—N1—C15
N2A—Re1—N1—C15
Re1—O4—C16—C17
Re1—O4—C16—C15
C18—C17—C16—O4
N5—C17—C16—O4
C18—C17—C16—C15
−34.9 (7)
98.48 (17)
−173.59 (17)
4.03 (16)
−77.9 (3)
−84.5 (6)
42 (4)
C19—N3—N4—C21
N3—N4—C21—C22
N3—N4—C21—C26
C26—C21—C22—C23
N4—C21—C22—C23
C22—C21—C26—C25
N4—C21—C26—C25
C22—C21—C26—C27
N4—C21—C26—C27
C2—Re1—N2—C41
C3—Re1—N2—C41
C1—Re1—N2—C41
O4—Re1—N2—C41
N1—Re1—N2—C41
N2A—Re1—N2—C41
C2—Re1—N2—C45
C3—Re1—N2—C45
C1—Re1—N2—C45
O4—Re1—N2—C45
N1—Re1—N2—C45
N2A—Re1—N2—C45
C45—N2—C41—C42
Re1—N2—C41—C42
N2—C41—C42—C43
C41—C42—C43—C44
C42—C43—C44—C45
C41—N2—C45—C44
Re1—N2—C45—C44
C43—C44—C45—N2
C21—C22—C23—C24
C22—C23—C24—C25
C23—C24—C25—C26
C21—C26—C25—C24
C27—C26—C25—C24
C18—C17—N5—N6
−178.0 (2)
−7.5 (4)
172.3 (2)
−0.7 (4)
179.1 (2)
1.1 (4)
−178.7 (2)
180.0 (3)
0.2 (4)
−48 (4)
−144 (4)
−174 (3)
133 (4)
147.8 (7)
−98 (3)
133 (4)
60.1 (7)
−38.5 (6)
−116.0 (7)
64 (7)
−140 (4)
133 (4)
−6 (5)
−44 (4)
−31.5 (9)
82 (4)
36 (4)
43 (4)
−119.1 (8)
142.3 (9)
64.7 (8)
−115 (8)
−3.0 (12)
177.7 (5)
0.6 (9)
−5.7 (3)
84.5 (2)
−150.1 (11)
−179.9 (2)
−96.8 (3)
−96.7 (6)
170.22 (19)
−99.59 (19)
25.8 (12)
−3.99 (17)
79.1 (3)
0.3 (9)
1.3 (13)
4.7 (16)
−176.0 (8)
−3.9 (16)
−0.3 (4)
0.7 (4)
79.2 (6)
175.27 (19)
−3.5 (3)
179.0 (2)
−1.9 (4)
−2.2 (4)
−0.2 (5)
−0.7 (4)
−179.5 (3)
9.9 (3)
Acta Cryst. (2013). C69, 1467-1471
sup-13

supplementary materials
N5—C17—C16—C15
C11—N1—C15—C14
Re1—N1—C15—C14
C11—N1—C15—C16
Re1—N1—C15—C16
O4—C16—C15—N1
C17—C16—C15—N1
O4—C16—C15—C14
C17—C16—C15—C14
C14—C13—C12—C11
N1—C15—C14—C13
C16—C15—C14—C13
N1—C15—C14—C19
C16—C15—C14—C19
C12—C13—C14—C15
C12—C13—C14—C19
C18—C19—C14—C15
N3—C19—C14—C15
C18—C19—C14—C13
N3—C19—C14—C13
C15—N1—C11—C12
Re1—N1—C11—C12
C13—C12—C11—N1
N3—C19—C18—C17
C14—C19—C18—C17
C16—C17—C18—C19
N5—C17—C18—C19
C2—Re1—C3—O3
176.9 (2)
0.3 (4)
C16—C17—N5—N6
−169.2 (2)
−177.2 (2)
162.8 (2)
−16.1 (4)
−2.7 (4)
176.1 (3)
3.7 (4)
C17—N5—N6—C31
−176.01 (19)
179.8 (2)
3.6 (3)
N5—N6—C31—C36
N5—N6—C31—C32
C36—C31—C32—C33
N6—C31—C32—C33
−0.1 (3)
−179.0 (2)
179.4 (2)
0.6 (4)
C32—C31—C36—C35
N6—C31—C36—C35
−175.2 (2)
−178.0 (3)
3.1 (4)
C32—C31—C36—C37
N6—C31—C36—C37
−0.3 (4)
0.7 (4)
C31—C36—C35—C34
C37—C36—C35—C34
C31—C32—C33—C34
C36—C35—C34—C33
C32—C33—C34—C35
C2—Re1—N2A—C41A
C3—Re1—N2A—C41A
C1—Re1—N2A—C41A
O4—Re1—N2A—C41A
N1—Re1—N2A—C41A
N2—Re1—N2A—C41A
C2—Re1—N2A—C45A
C3—Re1—N2A—C45A
C1—Re1—N2A—C45A
O4—Re1—N2A—C45A
N1—Re1—N2A—C45A
N2—Re1—N2A—C45A
C45A—N2A—C41A—C42A
Re1—N2A—C41A—C42A
N2A—C41A—C42A—C43A
C41A—C42A—C43A—C44A
C42A—C43A—C44A—C45A
C41A—N2A—C45A—C44A
Re1—N2A—C45A—C44A
C43A—C44A—C45A—N2A
−1.8 (4)
179.9 (3)
−0.2 (5)
−1.1 (5)
2.1 (5)
−178.9 (2)
−178.8 (2)
1.6 (4)
−0.6 (4)
178.9 (3)
−2.2 (4)
179.3 (2)
178.3 (3)
−0.1 (4)
−1.3 (4)
174.4 (2)
1.3 (5)
143.0 (19)
36 (14)
56 (2)
−44.0 (19)
−121 (2)
−120 (8)
−49 (2)
−156 (11)
−137 (2)
124 (2)
178.9 (2)
0.6 (4)
1.7 (4)
47 (2)
−177.4 (2)
−87 (5)
48 (6)
10 (4)
C1—Re1—C3—O3
0 (5)
178.2 (14)
−3 (3)
O4—Re1—C3—O3
100 (5)
N1—Re1—C3—O3
18E1 (10)
159 (5)
−3 (3)
N2—Re1—C3—O3
1 (4)
N2A—Re1—C3—O3
C18—C19—N3—N4
C14—C19—N3—N4
20 (14)
−11 (4)
7.3 (4)
−179 (2)
6 (4)
−174.4 (2)
Hydrogen-bond geometry (Å, º)
D—H···A
D—H
H···A
D···A
D—H···A
C12—H12···O2i
C41—H41···O4
C41—H41···O1ii
C44—H44···O4iii
0.95
0.95
0.95
0.95
2.52
2.50
2.59
2.35
3.142 (3)
2.913 (7)
3.459 (7)
3.166 (7)
123
106
152
143
Symmetry codes: (i) −x+2, −y+2, −z+2; (ii) −x+1, −y+1, −z+2; (iii) x+1, y, z.
Acta Cryst. (2013). C69, 1467-1471
sup-14

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