Crystal structure of 4′-{[4-(2,2′:6′,2′′-terpyrid­yl-4′-yl)phen­yl]ethyn­yl}biphenyl-4-yl (2,2,5,5-tetra­methyl-1-oxyl-3-pyrrolin-3-yl)formate benzene 2.5-solvate

Meyer, A.; Schnakenburg, G.; Schiemann, O.

doi:10.1107/S2056989015017697

research communications

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 71| Part 10| October 2015| Pages 1245-1249

doi:10.1107/S2056989015017697

Open

access

Crystal structure of 4′-{[4-(2,2′:6′,2′′-terpyridyl-4′-yl)phenyl]ethynyl}biphenyl-4-yl (2,2,5,5-tetramethyl-1-oxyl-3-pyrrolin-3-yl)formate benzene 2.5-solvate

Andreas Meyer,^a Gregor Schnakenburg ^b and Olav Schiemann ^a ^*

^aUniversity of Bonn, Institute of Physical and Theoretical Chemistry, Wegelerstr. 12, 53115 Bonn, Germany, and ^bUniversity of Bonn, Institute of Inorganic Chemistry, Gerhard-Domagk-Strasse 1, 53121 Bonn, Germany
^*Correspondence e-mail: schiemann@pc.uni-bonn.de

Edited by H. Stoeckli-Evans, University of Neuchâtel, Switzerland (Received 7 September 2015; accepted 21 September 2015; online 26 September 2015)

The title compound, C₄₄H₃₅N₄O₃·2.5C₆H₆ (1), consists of a terpyridine and a N-oxylpyrroline-3-formate group separated by an aromatic spacer, viz. 4-(phenylethynyl)-1,1′-biphenyl. It crystallized in the triclinic space group P-1 with two and a half benzene solvate molecules (one benzene molecule is located about an inversion center), while the dichloromethane solvate (2) of the same molecule [Ackermann et al. (2015 ). Chem. Commun. 51, 5257–5260] crystallized in the tetragonal space group P4₂/n, with considerable disorder in the molecule. In (1), the terpyridine (terpy) group assumes an all-trans conformation typical for terpyridines. It is essentially planar with the two outer pyridine rings (B and C) inclined to the central pyridine ring (A) by 8.70 (15) and 14.55 (14)°, respectively. The planes of the aromatic spacer (D, E and F) are nearly coplanar with dihedral angles D/E, D/F and E/F being 3.42 (15), 5.80 (15) and 4.00 (16)°, respectively. It is twisted with respect to the terpy group with, for example, dihedral angle A/D being 24.48 (14)°. The mean plane of the N-oxylpyrroline is almost normal to the biphenyl ring F, making a dihedral angle of 86.57 (16)°, and it is inclined to pyridine ring A by 72.61 (15)°. The intramolecular separation between the O atom of the nitroxyl group and the N atom of the central pyridine ring of the terpyridine group is 25.044 (3) Å. In the crystal, molecules are linked by pairs of C—H⋯O hydrogen bonds, forming inversion dimers. The dimers stack along the c axis forming columns. Within and between the columns, the spaces are occupied by benzene molecules. The shortest oxygen–oxygen separation between nitroxyl groups is 4.004 (4) Å. The details of the title compound are compared with those of the dichloromethane solvate (2) and with the structure of a related molecule, 4′-{4-[(2,2,5,5-tetramethyl-N-oxyl-3-pyrrolin-3-yl)ethynyl]phenyl}-2,2′:6′,2′′-terpyridine (3), which has an ethynylphenyl spacer [Meyer et al. (2015). Acta Cryst. E71, 870–874].

Keywords: crystal structure; terpyridine; nitroxyl; nitroxide; phenylethynylbiphenyl; ethynylphenyl; C—H⋯π interactions; π–π interactions; hydrogen bonds.

CCDC reference: 1426093

1. Chemical context

The title compound (1) was synthesized as a ligand for 3d metal ions in the framework of a pulsed EPR study on metal–nitroxyl model systems. It contains a nitroxyl group and a terpyridine (terpy) group which is capable of taking up metal ions. The title compound resembles compound (3) (4′-{4-[(2,2,5,5-tetramethyl-N-oxyl-3-pyrrolin-3-yl)ethynyl]phenyl}-2,2′:6′,2′′-terpyridine), which has an ethynylphenyl spacer (Meyer et al., 2015a ), compared to the phenylethynylbiphenyl spacer in the title compound (1). Nitroxyls are of interest in various branches of chemistry including magnetochemistry (Rajca et al., 2006 ; Fritscher et al., 2002 ), synthetic chemistry (Hoover & Stahl, 2011 ; Fey et al., 2001 ) and structural biology (Reginsson & Schiemann, 2011 ). Terpyridines show pH-dependent luminescence properties which have been analyzed in terms of a pH-dependent cis–trans isomerization (Nakamoto, 1960 ; Fink & Ohnesorge, 1970 ). Structural investigations in the solid state reveal an exclusive preference for the trans conformation (Fallahpour et al., 1999 ; Eryazici et al., 2006 ; Bessel et al., 1992 ; Grave et al., 2003 ). Terpyridines have been shown to be versatile ligands for various metal ions (Hogg & Wilkins, 1962 ; Constable et al., 1999 ; Narr et al., 2002 ; Meyer et al., 2015b ; Folgado et al., 1990 ).

2. Structural commentary

The molecular structure of the title compound, (1), is shown in Fig. 1. The crystal structure of the dichloromethane solvate (2) of the title compound has been reported (Ackermann et al., 2015). However, these authors used a different protocol for the crystallization of (1) and the conformation of (2) differs markedly from the one presented herein, as shown in the structural overlay of the two compounds (Fig. 2). The structural overlay of compounds (1) and (3) also illustrate the differences in their conformations (Fig. 3).

Figure 1
The molecular structure of the title compound (1), with atom labelling. Displacement ellipsoids are drawn at 50% probability level. The benzene molecules and the H atoms have been omitted for clarity.

Figure 2
The structural overlay of compounds (1) and (2) [title compound (1) blue, compound (2 – the dichloromethane solvate (Ackermann et al., 2015

) – red].

Figure 3
The structural overlay of compounds (1) and (3) [title compound (1) blue, compound (3) – (Meyer et al., 2015a

) – green].

In (1) the terpy group assumes the usual all–trans conformation (Meyer et al., 2015a; Fallahpour et al., 1999; Eryazici et al., 2006; Bessel et al., 1992; Grave et al., 2003). It is essentially planar with the two outer rings B (N3/C35–C39) and C (N4/C40–C44) being inclined to the central pyridine ring A (N2/C30–C34) by 8.70 (15) and 14.55 (14)°, respectively. The conformation of the nitroxyl group in (1) is similar to that found in (3), with a planar pyrroline (N1/C1–C4) ring assuming an angle of 72.61 (15)° to the central pyridine ring A [see also Margraf et al. (2009 ) and Schuetz et al. (2010 )]. In (3) this dihedral angle is 88.44 (7)°, while in (2) the same dihedral angle is 21.6 (2)°.

The N-oxylpyrroline-3-formate subunit is linked by a rigid spacer, consisting of a 4,4′-biphenylene, an ethynylene and a p-phenylene group, to the terpy subunit. The intramolecular separation of the nitroxyl and the terpy group is 25.044 (3) Å (measured between O1 and N2). The three phenyl groups within the spacer are nearly coplanar, with dihedral angles between the rings of 4.00 (16)°, for rings D (C10–C15) and E (C16–C21), and 3.42 (15)° for rings E and F (C24–C29). Compared to the structure of (3), the spacer is closer to coplanarity to the central pyridine ring: dihedral angle A/D is 24.48 (14)°, compared to 51.36 (7)° in (3). The ethynylene group is slightly bent as in (3), with angle C19–C22–C23 = 174.6 (3) and C22–C23–C24 = 177.8 (3)°. There are short C—H⋯N contacts in the molecule of 2.48 Å (H31⋯N3) and 2.49 Å (H34⋯N4). The same short contacts are also observed in (3). Such contacts have been classified as hydrogen bonds by Murguly et al. (1999 ).

3. Supramolecular features

In the crystal of (1), Fig. 4, molecules form layers which are nearly coplanar with the (0 $[\overline{1}]$ 1) plane. Neighbouring layers differ in the orientation of the molecules and each layer is separated by layers of solvent molecules. This arrangement possibly leads to favorable dispersive interactions although only one short C—H⋯π contact is observed between the solvent molecules and molecules of (1) (Table 1). Short π–π contacts are observed between the C rings of neighbouring molecules and between the B and C rings (Fig. 5). The centroid-to-centroid distances are 3.678 (2) and 3.8915 (18) Å, respectively, and can be classified as slipped face-to-face π-interactions (Janiak, 2000 ).

Table 1
Hydrogen-bond geometry (Å, °)

Cg4, Cg7 and Cg10 are the centroids of pyridine ring N4/C40–C44, spacer ring C24–C29 and benzene ring C54–C59, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C37—H37⋯O1ⁱ	0.95	2.65	3.228 (4)	120
C38—H38⋯O2ⁱⁱ	0.95	2.55	3.485 (4)	169
C6—H6C⋯O1ⁱⁱⁱ	0.98	2.61	3.499 (4)	151
C9—H9B⋯Cg4^iv	0.96	2.79	3.602 (4)	140
C14—H14⋯Cg10^v	0.95	2.88	3.608 (4)	134
C14—H14⋯Cg10^vi	0.95	2.88	3.608 (4)	134
C55—H55⋯Cg7^vii	0.95	2.90	3.680 (3)	140
Symmetry codes: (i) x+3, y+1, z+1; (ii) -x+4, -y+1, -z+1; (iii) -x, -y, -z; (iv) x-2, y-1, z-1; (v) x-1, y, z; (vi) -x+2, -y, -z+1; (vii) -x+3, -y+1, -z+1.

Figure 4
Crystal packing of the title compound viewed along the a axis. Weak C—H⋯O hydrogen bonds are shown as dashed lines (see Table 1

). H atoms not involved in C—H⋯O bonds have been omitted for clarity.

Figure 5
π-stacking interactions between pyridine rings of neighboring molecules. H atoms have been omitted for clarity.

Within the planes, there are weak C—H⋯O hydrogen bonds between the nitroxyl-O atom and the para-hydrogen atom of pyridine ring B (Table 1). Furthermore, two weak hydrogen bonds per molecule are formed between pairs of layers (Table 1). One of these hydrogen bonds involves the nitroxyl O atom and a hydrogen atom of a methyl group of a molecule from a neighboring layer. The other hydrogen bond is formed between the carbonylic O atom of the carboxylate group and a meta-hydrogen atom of one of the outer pyridine rings of a molecule from a neighboring layer. As the layers are hydrogen bonded pair-wise, the structure can also be described as consisting of double-layers.

It is noteworthy that the arrangement of the molecules of the title compound strongly depends upon the solvents of crystallization. In compound (1), the molecules are arranged in layers and the benzene molecules fill out the channels between the layers formed by the aromatic spacers of the molecule. Close intermolecule contacts exist only between the functional groups. In the structure of (2) (Ackermann et al., 2015), the solvent of crystallization is dichloromethane instead of benzene and molecules are arranged having fourfold rotational site symmetry. The solvent molecules fill out channels between the molecules of (2), as in (1). However, the CH₂Cl₂ solvent molecules in (2) are in close proximity to the terpyridine groups instead of to the aromatic spacer. Weak hydrogen bonds are formed predominantly involving the O atoms as acceptors and the pyrroline and the pyridine rings as donors, as observed in (2) and (3). The shortest oxygen–oxygen separation between neighboring nitroxyl groups is 4.004 (4) Å. This O⋯O distance is an important factor determining the strength of through space exchange interactions of nitroxyls (Rajca et al. 2006).

4. Database survey

The Cambridge Structural Database (CSD, Version 5.36; Groom & Allen, 2014 ) has not been updated since our presentation of the structure of (2). The CSD query revealed, that non-coordinated terpyridines are arranged in an all-trans conformation, unless they are either protonated, lithiated or cannot assume an all-trans conformation for reasons of steric hindrance.

5. Synthesis and crystallization

The synthesis of the title compound (1), is illustrated in Fig. 6. 480 mg (1.45 mmol) of 4′-(4-ethynylphenyl)-2,2′:6′,2′′-terpyridine (Grosshenny & Ziessel, 1993 ), 780 mg (1.69 mmol) of 4′-iodo-p-biphen-4-yl-N-oxyl-2,2,5,5-tetramethylpyrroline-3-formate (Bode et al., 2008 ) and 85 mg (0.12 mmol) of tetrakis(triphenylphosphane)palladium(0) were dissolved in a mixture of 20 ml of triethylamine (TEA) and 9 ml of dimethylformamide (DMF) giving rise to an orange solution. The solution was heated to 323 K and stirred for 8 h after which the solvents were removed under reduced pressure. The resulting dark-orange powder was dissolved in dichloromethane (DCM) and subjected to column chromatography using aluminum oxide (5% water, height 30 cm, diameter 2.3 cm). First, a mixture of DCM and hexane in a 1:2 ratio was used as eluent until all remaining educt, reagents and side products were eluted (approximately 200–300 ml). The column was then eluted using pure DCM to obtain a yellow solution. Removing the solvent yielded the product as a pale-yellow solid (yield: 90%). Crystals suitable for X-ray crystallography were obtained by layering a solution of (1) in benzene with n-hexane.

Figure 6
The synthesis of the title compound (1).

6. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2. The H atoms were included in calculated positions and treated as riding atoms: C-H = 0.95-0.98 Å with U_iso(H) = 1.5U_eq(C) for methyl H atoms and 1.2U_eq(C) for other H atoms. 16 reflections with bad agreement were omitted from the final refinement cycles.

Table 2
Experimental details

Crystal data
Chemical formula	C₄₄H₃₅N₄O₃·2.5C₆H₆
M_r	863.03
Crystal system, space group	Triclinic, P $[\overline{1}]$
Temperature (K)	123
a, b, c (Å)	5.7578 (1), 18.0559 (4), 23.3716 (6)
α, β, γ (°)	105.5870 (13), 93.7408 (13), 92.6002 (14)
V (Å³)	2330.41 (9)
Z	2
Radiation type	Mo Kα
μ (mm⁻¹)	0.08
Crystal size (mm)	0.28 × 0.20 × 0.08

Data collection
Diffractometer	Nonius KappaCCD
Absorption correction	Multi-scan (SORTAV; Blessing, 1995 )
T_min, T_max	0.808, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	74528, 11227, 6356
R_int	0.109
(sin θ/λ)_max (Å⁻¹)	0.661

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.071, 0.217, 1.07
No. of reflections	11227
No. of parameters	587
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.33, −0.27
Computer programs: HKL DENZO and SCALEPACK (Otwinowski & Minor 1997 ), SHELXS97 (Sheldrick,2008 ), SHELXL2013 (Sheldrick, 2015 ), OLEX2 (Dolomanov et al., 2009 ) and Mercury (Macrae et al., 2008 ).

Supporting information

CCDC reference: 1426093

Crystal structure: contains datablock I. DOI: 10.1107/S2056989015017697/su5206sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S2056989015017697/su5206Isup2.hkl

checkCIF report

Chemical context top

The title compound (1) was synthesized as a ligand for 3d metal ions in the framework of a pulsed EPR study on metal–nitroxyl model systems. It contains a nitroxyl group and a terpyridine (terpy) group which is capable of taking up metal ions. The title compound resembles compound (3) (4'-{4-[(2,2,5,5-tetramethyl-N-oxyl-3-pyrrolin-3-yl)ethynyl]phenyl}-2,2':6',2''-terpyridine), which has an ethynylphenyl spacer (Meyer et al., 2015a), compared to the phenylethynylbiphenyl spacer in the title compound (1). Nitroxyls are of interest in various branches of chemistry including magnetochemistry (Rajca et al., 2006; Fritscher et al., 2002), synthetic chemistry (Hoover & Stahl, 2011; Fey et al., 2001) and structural biology (Reginsson & Schiemann, 2011). Terpyridines show pH-dependent luminescence properties which have been analyzed in terms of a pH-dependent cis–trans isomerization (Nakamoto, 1960; Fink & Ohnesorge, 1970). Structural investigations in the solid state reveal an exclusive preference for the trans conformation (Fallahpour et al., 1999; Eryazici et al., 2006; Bessel et al., 1992; Grave et al., 2003). Terpyridines have been shown to be versatile ligands for various metal ions (Hogg & Wilkins, 1962; Constable et al., 1999; Narr et al., 2002; Meyer et al., 2015b; Folgado et al., 1990).

Structural commentary top

In (1) the terpy group assumes the usual all–trans conformation (Meyer et al., 2015a; Fallahpour et al., 1999; Eryazici et al., 2006; Bessel et al., 1992; Grave et al., 2003). It is essentially planar with the two outer rings B (N3/C35–C39) and C (N4/C40–C44) being inclined to the central pyridine ring A (N2/C30–C34) by 8.70 (15) and 14.55 (14)°, respectively. The conformation of the nitroxyl group in (1) is similar to that found in (3), with a planar pyrroline (N1/C1–C4) ring assuming an angle of 72.61 (15)° to the central pyridine ring A [see also Margraf et al. (2009) and Schuetz et al. (2010)]. In (3) this dihedral angle is 88.44 (7)°, while in (2) the same dihedral angle is 21.6 (2)°.

The N-oxylpyrroline-3-formate subunit is linked by a rigid spacer, consisting of a 4,4'biphenylene, an ethynylene and a p-phenylene group, to the terpy subunit. The intramolecular separation of the nitroxyl and the terpy group is 25.044 (3) Å (measured between O1 and N2). The three phenyl groups within the spacer are nearly coplanar, with dihedral angles between the rings of 4.00 (16)°, for rings D (C10–C15) and E (C16–C21), and 3.42 (15)° for rings E and F (C24–C29). Compared to the structure of (3), the spacer is closer to coplanarity to the central pyridine ring: dihedral angle A/D is 24.48 (14)°, compared to 51.36 (7)° in (3). The ethynylene group is slightly bent as in (3), with angle C19–C22–C23 = 174.6 (3) and C22–C23–C24 = 177.8 (3)°. There are short C—H···N contacts in the molecule of 2.48 Å (H31···N3) and 2.49 Å (H34···N4). The same short contacts are also observed in (3). Such contacts have been classified as hydrogen bonds by Murguly et al. (1999).

Supramolecular features top

In the crystal of (1), Fig. 4, molecules form layers which are nearly coplanar with the (011) plane. Neighbouring layers differ in the orientation of the molecules and each layer is separated by layers of solvent molecules. This arrangement possibly leads to favorable dispersive interactions although only one short C—H···π contact is observed between the solvent molecules and molecules of (1) (Table 1). Short π–π contacts are observed between the C rings of neighbouring molecules and between the B and C rings (Fig. 5). The centroid-to-centroid distances are 3.678 (2) and 3.8915 (18) Å, respectively, and can be classified as slipped face-to-face π-interactions (Janiak, 2000).

Within the planes, there are weak C—H···O hydrogen bonds between the nitroxyl-O atom and the para-hydrogen atom of pyridine ring B (Table 1). Furthermore, two weak hydrogen bonds per molecule are formed between pairs of layers (Table 1). One of these hydrogen bonds involves the nitroxyl O atom and a hydrogen atom of a methyl group of a molecule from a neighboring layer. The other hydrogen bond is formed between the carbonylic O atom of the carboxylate group and a meta-hydrogen atom of one of the outer pyridine rings of a molecule from a neighboring layer. As the layers are hydrogen bonded pair-wise, the structure can also be described as consisting of double-layers.

It is noteworthy that the arrangement of the molecules of the title compound strongly depends upon the solvents of crystallization. In compound (1), the molecules are arranged in layers and the benzene molecules fill out the channels between the layers formed by the aromatic spacers of the molecule. Close intermolecule contacts exist only between the functional groups. In the structure of (2) (Ackermann et al., 2015), the solvent of crystallization is dichloromethane instead of benzene and molecules are arranged having fourfold rotational site symmetry. The solvent molecules fill out channels between the molecules of (2), as in (1). However, the CH₂Cl₂ solvent molecules in (2) are in close proximity to the terpyridine groups instead of to the aromatic spacer. Weak hydrogen bonds are formed predominantly involving the O atoms as acceptors and the pyrroline and the pyridine rings as donors, as observed in (2) and (3). The shortest oxygen–oxygen separation between neighboring nitroxyl groups is 4.004 (4) Å. This O···O distance is an important factor determining the strength of through space exchange interactions of nitroxyls (Rajca et al. 2006).

Database survey top

The Cambridge Structural Database (CSD, Version 5.36; Groom & Allen, 2014) has not been updated since our presentation of the structure of (2). The CSD query revealed, that non-coordinated terpyridines are arranged in an all-trans conformation, unless they are either protonated, lithiated or cannot assume an all-trans conformation for reasons of steric hindrance.

Synthesis and crystallization top

The synthesis of the title compound (1), is illustrated in Fig. 6. 480 mg (1.45 mmol) of 4'-(4-ethynylphenyl)-2,2':6',2''-terpyridine (Grosshenny & Ziessel, 1993), 780 mg (1.69 mmol) of 4'-iodo-p-biphen-4-yl-N- oxyl-2,2,5,5-tetramethylpyrroline-3-formate (Bode et al., 2008) and 85 mg (0.12 mmol) of tetrakis(triphenylphosphane)palladium(0) were dissolved in a mixture of 20 ml of triethylamine (TEA) and 9 ml of dimethylformamide (DMF) giving rise to an orange solution. The solution was heated to 323 K and stirred for 8 h after which the solvents were removed under reduced pressure. The resulting dark-orange powder was dissolved in dichloromethane (DCM) and subjected to column chromatography using aluminum oxide (5% water, height 30 cm, diameter 2.3 cm). First, a mixture of DCM and hexane in a 1:2 ratio was used as eluent until all remaining educt, reagents and side products were eluted (approximately 200–300 ml). The column was then eluted using pure DCM to obtain a yellow solution. Removing the solvent yielded the product as a pale-yellow solid (yield: 90%). Crystals suitable for X-ray crystallography were obtained by layering a solution of (1) in benzene with n-hexane.

Refinement top

Crystal data, data collection and structure refinement details are summarized in Table 2. The H atoms were included in calculated positions and treated as riding atoms: C—H = 0.95-0.98 Å with U_iso(H) = 1.5U_eq(C) for methyl H atoms and 1.2U_eq(C) for other H atoms. 16 reflections with bad agreement were omitted from the final refinement cycles.

Related literature top

For related literature, see: Ackermann et al. (2015); Bessel et al. (1992); Bode et al. (2008); Constable et al. (1999); Eryazici et al. (2006); Fallahpour et al. (1999); Fey et al. (2001); Fink & Ohnesorge (1970); Folgado et al. (1990); Fritscher et al. (2002); Grave et al. (2003); Groom & Allen (2014); Grosshenny & Ziessel (1993); Hogg & Wilkins (1962); Hoover & Stahl (2011); Janiak (2000); Margraf et al. (2009); Meyer et al. (2015a, 2015b); Murguly et al. (1999); Nakamoto (1960); Narr et al. (2002); Rajca et al. (2006); Reginsson & Schiemann (2011); Schuetz et al. (2010).

Computing details top

Data collection: HKL DENZO and SCALEPACK (Otwinowski & Minor 1997); cell refinement: HKL SCALEPACK (Otwinowski & Minor 1997); data reduction: HKL DENZO and SCALEPACK (Otwinowski & Minor 1997); program(s) used to solve structure: SHELXS97 (Sheldrick,2008); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2015); molecular graphics: Olex2 (Dolomanov et al., 2009) and Mercury (Macrae et al., 2008); software used to prepare material for publication: Olex2 (Dolomanov et al., 2009).

Figures top

	Fig. 1. The molecular structure of the title compound (1), with atom labelling. Displacement ellipsoids are drawn at 50% probability level. The benzene molecules and the H atoms have been omitted for clarity.
	Fig. 2. The structural overlay of compounds (1) and (2) [title compound (1) blue, compound (2 – the dichloromethane solvate (Ackermann et al., 2015) – red].
	Fig. 3. The structural overlay of compounds (1) and (3) [title compound (1) blue, compound (3) – (Meyer et al., 2015a) – green].
	Fig. 4. Crystal packing of the title compound viewed along the a axis. Weak C—H···O hydrogen bonds are shown as dashed lines (see Table 1). H atoms not involved in C—H···O bonds have been omitted for clarity.
	Fig. 5. π-stacking interactions between pyridine rings of neighboring molecules. H atoms have been omitted for clarity.
	Fig. 6. The synthesis of the title compound (1).

4'-{[4-(2,2':6',2''-Terpyridyl-4'-yl)phenyl]ethynyl}biphenyl-4-yl (2,2,5,5-tetramethyl-1-oxyl-3-pyrrolin-3-yl)formate benzene 2.5-solvate top

Crystal data top

C₄₄H₃₅N₄O₃·2.5C₆H₆	Z = 2
M_r = 863.03	F(000) = 912
Triclinic, P1	D_x = 1.230 Mg m⁻³
a = 5.7578 (1) Å	Mo Kα radiation, λ = 0.71073 Å
b = 18.0559 (4) Å	Cell parameters from 12020 reflections
c = 23.3716 (6) Å	θ = 1.0–29.1°
α = 105.5870 (13)°	µ = 0.08 mm⁻¹
β = 93.7408 (13)°	T = 123 K
γ = 92.6002 (14)°	Plate, yellow
V = 2330.41 (9) Å³	0.28 × 0.20 × 0.08 mm

Data collection top

Nonius KappaCCD diffractometer	6356 reflections with I > 2σ(I)
fine slicing φ and ω scans	R_int = 0.109
Absorption correction: multi-scan (SORTAV; Blessing, 1995)	θ_max = 28.0°, θ_min = 1.8°
T_min = 0.808, T_max = 1.000	h = −7→7
74528 measured reflections	k = −23→23
11227 independent reflections	l = −30→30

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.071	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.217	H-atom parameters constrained
S = 1.07	w = 1/[σ²(F_o²) + (0.0715P)² + 2.806P] where P = (F_o² + 2F_c²)/3
11227 reflections	(Δ/σ)_max < 0.001
587 parameters	Δρ_max = 0.33 e Å⁻³
1 restraint	Δρ_min = −0.27 e Å⁻³

Crystal data top

C₄₄H₃₅N₄O₃·2.5C₆H₆	γ = 92.6002 (14)°
M_r = 863.03	V = 2330.41 (9) Å³
Triclinic, P1	Z = 2
a = 5.7578 (1) Å	Mo Kα radiation
b = 18.0559 (4) Å	µ = 0.08 mm⁻¹
c = 23.3716 (6) Å	T = 123 K
α = 105.5870 (13)°	0.28 × 0.20 × 0.08 mm
β = 93.7408 (13)°

Data collection top

Nonius KappaCCD diffractometer	11227 independent reflections
Absorption correction: multi-scan (SORTAV; Blessing, 1995)	6356 reflections with I > 2σ(I)
T_min = 0.808, T_max = 1.000	R_int = 0.109
74528 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.071	1 restraint
wR(F²) = 0.217	H-atom parameters constrained
S = 1.07	Δρ_max = 0.33 e Å⁻³
11227 reflections	Δρ_min = −0.27 e Å⁻³
587 parameters

Special details top

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

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

	x	y	z	U_iso*/U_eq
C1	0.2370 (5)	−0.01295 (16)	0.10190 (12)	0.0227 (6)
C2	0.3869 (5)	−0.03265 (16)	0.15104 (12)	0.0228 (6)
C3	0.4509 (5)	−0.10465 (16)	0.13551 (13)	0.0243 (6)
H3	0.5452	−0.1260	0.1611	0.029*
C4	0.3597 (5)	−0.14879 (16)	0.07364 (13)	0.0258 (6)
C5	−0.0104 (5)	0.00458 (18)	0.11846 (14)	0.0299 (7)
H5A	−0.1095	0.0036	0.0825	0.045*
H5B	−0.0082	0.0557	0.1468	0.045*
H5C	−0.0727	−0.0343	0.1367	0.045*
C6	0.3447 (5)	0.04980 (17)	0.07767 (14)	0.0294 (7)
H6A	0.5016	0.0368	0.0661	0.044*
H6B	0.3544	0.0991	0.1085	0.044*
H6C	0.2475	0.0539	0.0428	0.044*
C7	0.4547 (5)	0.02506 (17)	0.20817 (13)	0.0242 (6)
C8	0.5527 (5)	−0.17353 (18)	0.03214 (14)	0.0319 (7)
H8A	0.4832	−0.1971	−0.0085	0.048*
H8B	0.6441	−0.2110	0.0456	0.048*
H8C	0.6548	−0.1284	0.0326	0.048*
C9	0.1932 (5)	−0.21795 (18)	0.07291 (15)	0.0343 (7)
H9A	0.0694	−0.2006	0.0993	0.051*
H9B	0.2799	−0.2562	0.0867	0.051*
H9C	0.1238	−0.2412	0.0322	0.051*
C10	0.6996 (5)	0.04666 (16)	0.29676 (13)	0.0280 (7)
C11	0.9052 (6)	0.08515 (19)	0.29138 (14)	0.0358 (7)
H11	0.9637	0.0790	0.2534	0.043*
C12	1.0255 (6)	0.13289 (19)	0.34188 (14)	0.0342 (7)
H12	1.1682	0.1591	0.3381	0.041*
C13	0.9437 (5)	0.14379 (16)	0.39818 (13)	0.0256 (6)
C14	0.7358 (5)	0.10257 (19)	0.40168 (14)	0.0330 (7)
H14	0.6767	0.1076	0.4395	0.040*
C15	0.6137 (6)	0.05439 (19)	0.35106 (14)	0.0342 (7)
H15	0.4721	0.0271	0.3542	0.041*
C16	1.0710 (5)	0.19732 (17)	0.45189 (13)	0.0253 (6)
C17	1.2858 (6)	0.23439 (19)	0.44816 (14)	0.0360 (8)
H17	1.3476	0.2258	0.4104	0.043*
C18	1.4098 (6)	0.2824 (2)	0.49680 (14)	0.0361 (8)
H18	1.5546	0.3067	0.4922	0.043*
C19	1.3264 (5)	0.29639 (17)	0.55323 (13)	0.0285 (7)
C20	1.1098 (6)	0.2615 (2)	0.55805 (14)	0.0366 (8)
H20	1.0467	0.2711	0.5957	0.044*
C21	0.9861 (5)	0.21278 (19)	0.50809 (14)	0.0345 (7)
H21	0.8395	0.1893	0.5123	0.041*
C22	1.4677 (5)	0.34418 (17)	0.60378 (14)	0.0299 (7)
C23	1.6001 (5)	0.38338 (17)	0.64283 (13)	0.0288 (7)
C24	1.7619 (5)	0.43207 (17)	0.68813 (13)	0.0273 (6)
C25	1.9752 (5)	0.45919 (17)	0.67281 (13)	0.0296 (7)
H25	2.0113	0.4455	0.6324	0.036*
C26	2.1331 (5)	0.50571 (17)	0.71624 (13)	0.0285 (7)
H26	2.2755	0.5242	0.7051	0.034*
C27	2.0868 (5)	0.52596 (15)	0.77632 (13)	0.0235 (6)
C28	1.8728 (5)	0.49925 (16)	0.79124 (13)	0.0256 (6)
H28	1.8368	0.5129	0.8317	0.031*
C29	1.7132 (5)	0.45334 (16)	0.74799 (13)	0.0265 (6)
H29	1.5689	0.4361	0.7591	0.032*
C30	2.2616 (5)	0.57301 (15)	0.82326 (12)	0.0230 (6)
C31	2.4348 (5)	0.62120 (16)	0.80997 (13)	0.0247 (6)
H31	2.4364	0.6278	0.7710	0.030*
C32	2.6059 (5)	0.65965 (16)	0.85480 (12)	0.0241 (6)
C33	2.4383 (5)	0.60956 (16)	0.92376 (13)	0.0240 (6)
C34	2.2643 (5)	0.56824 (16)	0.88191 (12)	0.0244 (6)
H34	2.1482	0.5370	0.8931	0.029*
C35	2.7986 (5)	0.70819 (16)	0.84142 (13)	0.0249 (6)
C36	2.9585 (5)	0.75177 (17)	0.88581 (14)	0.0292 (7)
H36	2.9416	0.7538	0.9264	0.035*
C37	3.1439 (5)	0.79252 (17)	0.87052 (14)	0.0310 (7)
H37	3.2553	0.8228	0.9004	0.037*
C38	3.1634 (6)	0.78823 (18)	0.81163 (14)	0.0337 (7)
H38	3.2898	0.8146	0.7996	0.040*
C39	2.9941 (6)	0.7444 (2)	0.77017 (15)	0.0388 (8)
H39	3.0071	0.7421	0.7294	0.047*
C40	2.4478 (5)	0.60351 (15)	0.98644 (12)	0.0236 (6)
C41	2.6483 (5)	0.62869 (17)	1.02509 (13)	0.0279 (6)
H41	2.7844	0.6482	1.0117	0.033*
C42	2.6446 (6)	0.62468 (18)	1.08338 (13)	0.0320 (7)
H42	2.7765	0.6429	1.1111	0.038*
C43	2.4456 (6)	0.59362 (18)	1.10055 (14)	0.0333 (7)
H43	2.4384	0.5898	1.1402	0.040*
C44	2.2573 (6)	0.56820 (18)	1.05891 (14)	0.0324 (7)
H44	2.1224	0.5461	1.0709	0.039*
C45	0.4296 (6)	0.3900 (2)	0.35899 (16)	0.0421 (8)
H45	0.2895	0.3889	0.3349	0.050*
C46	0.4922 (7)	0.4522 (2)	0.40689 (16)	0.0465 (9)
H46	0.3934	0.4938	0.4163	0.056*
C47	0.6977 (7)	0.4549 (2)	0.44152 (17)	0.0527 (10)
H47	0.7416	0.4984	0.4743	0.063*
C48	0.8395 (7)	0.3934 (3)	0.42804 (18)	0.0557 (11)
H48	0.9812	0.3948	0.4516	0.067*
C49	0.7751 (7)	0.3310 (2)	0.38076 (17)	0.0507 (10)
H49	0.8713	0.2887	0.3717	0.061*
C50	0.5700 (7)	0.3294 (2)	0.34612 (16)	0.0446 (9)
H50	0.5262	0.2861	0.3132	0.053*
C51	0.7877 (6)	0.84135 (17)	0.29690 (18)	0.101 (2)
H51	0.6861	0.8779	0.3170	0.121*
C52	0.9878 (6)	0.86602 (14)	0.27527 (19)	0.0911 (18)
H52	1.0230	0.9195	0.2805	0.109*
C53	1.1364 (5)	0.8125 (2)	0.24592 (18)	0.097 (2)
H53	1.2732	0.8293	0.2311	0.117*
C54	1.0849 (6)	0.73429 (18)	0.23820 (15)	0.0828 (16)
H54	1.1864	0.6977	0.2181	0.099*
C55	0.8848 (6)	0.70963 (13)	0.25983 (16)	0.0666 (13)
H55	0.8495	0.6562	0.2546	0.080*
C56	0.7362 (5)	0.76315 (19)	0.28918 (17)	0.0800 (16)
H56	0.5994	0.7463	0.3040	0.096*
C57	1.2877 (8)	0.0159 (4)	0.4782 (3)	0.0794 (17)
H57	1.1403	0.0270	0.4629	0.095*
C58	1.3994 (10)	0.0665 (3)	0.5279 (3)	0.0766 (15)
H58	1.3291	0.1122	0.5471	0.092*
C59	1.6137 (11)	0.0509 (4)	0.5499 (3)	0.0865 (17)
H59	1.6928	0.0860	0.5841	0.104*
N1	0.2293 (4)	−0.08860 (14)	0.05611 (11)	0.0272 (5)
N2	2.6094 (4)	0.65448 (13)	0.91102 (10)	0.0233 (5)
N3	2.8130 (5)	0.70501 (16)	0.78374 (11)	0.0348 (6)
N4	2.2537 (4)	0.57284 (14)	1.00265 (11)	0.0286 (6)
O1	0.1208 (4)	−0.10055 (12)	0.00485 (9)	0.0358 (5)
O2	0.4049 (4)	0.09116 (12)	0.22097 (9)	0.0312 (5)
O3	0.5864 (4)	−0.00577 (12)	0.24535 (9)	0.0334 (5)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0219 (14)	0.0236 (14)	0.0216 (14)	0.0012 (11)	0.0000 (11)	0.0047 (11)
C2	0.0209 (13)	0.0238 (14)	0.0228 (14)	−0.0039 (11)	0.0002 (11)	0.0064 (11)
C3	0.0219 (14)	0.0243 (15)	0.0258 (15)	−0.0022 (11)	−0.0030 (11)	0.0070 (12)
C4	0.0251 (14)	0.0224 (14)	0.0275 (15)	−0.0001 (12)	−0.0033 (12)	0.0041 (12)
C5	0.0238 (15)	0.0324 (17)	0.0300 (17)	−0.0001 (13)	−0.0004 (12)	0.0036 (13)
C6	0.0287 (15)	0.0310 (16)	0.0288 (16)	−0.0024 (13)	−0.0009 (12)	0.0104 (13)
C7	0.0213 (14)	0.0265 (16)	0.0251 (15)	−0.0022 (12)	−0.0008 (11)	0.0087 (12)
C8	0.0319 (16)	0.0278 (16)	0.0333 (17)	0.0026 (13)	0.0014 (13)	0.0040 (13)
C9	0.0303 (16)	0.0278 (16)	0.0416 (19)	−0.0068 (13)	−0.0038 (14)	0.0071 (14)
C10	0.0353 (16)	0.0225 (15)	0.0220 (15)	−0.0013 (13)	−0.0093 (12)	0.0020 (12)
C11	0.0404 (18)	0.0417 (19)	0.0226 (16)	−0.0030 (15)	0.0012 (13)	0.0052 (14)
C12	0.0327 (17)	0.0395 (18)	0.0258 (16)	−0.0100 (14)	0.0016 (13)	0.0032 (14)
C13	0.0272 (15)	0.0255 (15)	0.0236 (15)	0.0014 (12)	−0.0021 (12)	0.0069 (12)
C14	0.0333 (17)	0.0409 (18)	0.0224 (16)	−0.0086 (14)	−0.0001 (13)	0.0070 (13)
C15	0.0324 (17)	0.0391 (18)	0.0276 (17)	−0.0108 (14)	−0.0033 (13)	0.0068 (14)
C16	0.0239 (14)	0.0285 (15)	0.0225 (15)	−0.0017 (12)	−0.0031 (11)	0.0067 (12)
C17	0.0350 (17)	0.045 (2)	0.0253 (16)	−0.0097 (15)	0.0019 (13)	0.0069 (14)
C18	0.0294 (16)	0.0439 (19)	0.0306 (17)	−0.0140 (14)	−0.0002 (13)	0.0059 (14)
C19	0.0288 (15)	0.0285 (16)	0.0254 (15)	−0.0020 (13)	−0.0055 (12)	0.0048 (12)
C20	0.0355 (17)	0.045 (2)	0.0228 (16)	−0.0098 (15)	0.0028 (13)	0.0007 (14)
C21	0.0299 (16)	0.0423 (19)	0.0264 (16)	−0.0095 (14)	0.0020 (13)	0.0027 (14)
C22	0.0293 (16)	0.0295 (16)	0.0286 (16)	−0.0029 (13)	−0.0015 (13)	0.0056 (13)
C23	0.0276 (15)	0.0311 (16)	0.0258 (16)	−0.0013 (13)	−0.0005 (12)	0.0057 (13)
C24	0.0282 (15)	0.0269 (15)	0.0247 (15)	−0.0016 (12)	−0.0040 (12)	0.0054 (12)
C25	0.0316 (16)	0.0307 (16)	0.0231 (15)	−0.0040 (13)	−0.0009 (12)	0.0032 (13)
C26	0.0265 (15)	0.0310 (16)	0.0258 (16)	−0.0039 (12)	−0.0012 (12)	0.0052 (13)
C27	0.0261 (14)	0.0180 (13)	0.0249 (15)	−0.0002 (11)	−0.0022 (11)	0.0047 (11)
C28	0.0247 (14)	0.0276 (15)	0.0236 (15)	−0.0021 (12)	−0.0014 (11)	0.0068 (12)
C29	0.0247 (14)	0.0260 (15)	0.0267 (16)	−0.0027 (12)	−0.0020 (12)	0.0051 (12)
C30	0.0242 (14)	0.0191 (14)	0.0244 (15)	−0.0009 (11)	−0.0001 (11)	0.0046 (11)
C31	0.0284 (15)	0.0235 (14)	0.0223 (15)	−0.0021 (12)	0.0013 (12)	0.0072 (12)
C32	0.0274 (15)	0.0222 (14)	0.0221 (15)	−0.0009 (12)	0.0000 (11)	0.0061 (11)
C33	0.0267 (14)	0.0207 (14)	0.0250 (15)	0.0011 (12)	0.0004 (12)	0.0073 (12)
C34	0.0270 (15)	0.0223 (14)	0.0243 (15)	−0.0023 (12)	0.0030 (12)	0.0075 (12)
C35	0.0292 (15)	0.0200 (14)	0.0238 (15)	−0.0009 (12)	0.0025 (12)	0.0031 (11)
C36	0.0308 (16)	0.0279 (16)	0.0271 (16)	−0.0054 (13)	−0.0001 (12)	0.0061 (13)
C37	0.0298 (16)	0.0253 (15)	0.0340 (17)	−0.0067 (13)	0.0000 (13)	0.0033 (13)
C38	0.0341 (17)	0.0300 (16)	0.0363 (18)	−0.0069 (13)	0.0060 (14)	0.0088 (14)
C39	0.046 (2)	0.044 (2)	0.0284 (17)	−0.0093 (16)	0.0064 (14)	0.0140 (15)
C40	0.0274 (15)	0.0191 (14)	0.0237 (15)	−0.0020 (11)	0.0011 (12)	0.0055 (11)
C41	0.0294 (15)	0.0266 (15)	0.0276 (16)	−0.0025 (12)	−0.0009 (12)	0.0089 (12)
C42	0.0380 (17)	0.0319 (17)	0.0252 (16)	0.0019 (14)	−0.0027 (13)	0.0075 (13)
C43	0.0464 (19)	0.0323 (17)	0.0230 (16)	0.0016 (14)	0.0025 (14)	0.0108 (13)
C44	0.0402 (18)	0.0302 (16)	0.0298 (17)	−0.0001 (14)	0.0037 (14)	0.0135 (13)
C45	0.0380 (19)	0.057 (2)	0.036 (2)	0.0008 (17)	0.0055 (15)	0.0213 (17)
C46	0.061 (2)	0.045 (2)	0.041 (2)	0.0118 (18)	0.0159 (18)	0.0194 (17)
C47	0.063 (3)	0.053 (2)	0.037 (2)	−0.012 (2)	0.0112 (18)	0.0051 (18)
C48	0.037 (2)	0.090 (3)	0.041 (2)	0.004 (2)	0.0034 (17)	0.021 (2)
C49	0.061 (2)	0.060 (3)	0.042 (2)	0.027 (2)	0.0204 (19)	0.026 (2)
C50	0.061 (2)	0.040 (2)	0.0322 (19)	−0.0056 (18)	0.0072 (17)	0.0103 (15)
C51	0.116 (5)	0.067 (3)	0.141 (6)	0.038 (3)	0.062 (4)	0.046 (4)
C52	0.081 (4)	0.060 (3)	0.152 (6)	0.009 (3)	0.020 (4)	0.059 (4)
C53	0.073 (3)	0.113 (5)	0.149 (6)	0.026 (3)	0.046 (4)	0.097 (4)
C54	0.099 (4)	0.069 (3)	0.088 (4)	0.040 (3)	0.028 (3)	0.025 (3)
C55	0.071 (3)	0.046 (2)	0.084 (3)	0.002 (2)	−0.015 (3)	0.025 (2)
C56	0.061 (3)	0.084 (4)	0.121 (5)	0.013 (3)	0.024 (3)	0.068 (3)
C57	0.048 (3)	0.109 (4)	0.119 (5)	0.026 (3)	0.031 (3)	0.088 (4)
C58	0.082 (4)	0.077 (4)	0.095 (4)	0.024 (3)	0.035 (3)	0.057 (3)
C59	0.093 (4)	0.102 (4)	0.088 (4)	−0.014 (4)	0.015 (3)	0.068 (4)
N1	0.0300 (13)	0.0256 (13)	0.0215 (13)	0.0024 (10)	−0.0069 (10)	0.0008 (10)
N2	0.0258 (12)	0.0205 (12)	0.0223 (12)	−0.0009 (10)	0.0013 (10)	0.0043 (10)
N3	0.0401 (15)	0.0379 (15)	0.0256 (14)	−0.0101 (12)	0.0026 (11)	0.0092 (12)
N4	0.0301 (13)	0.0276 (13)	0.0286 (14)	−0.0056 (11)	0.0028 (10)	0.0093 (11)
O1	0.0413 (13)	0.0371 (12)	0.0238 (11)	0.0037 (10)	−0.0113 (9)	0.0023 (9)
O2	0.0334 (11)	0.0276 (12)	0.0290 (12)	0.0003 (9)	−0.0022 (9)	0.0028 (9)
O3	0.0464 (13)	0.0265 (11)	0.0220 (11)	−0.0053 (10)	−0.0143 (9)	0.0030 (9)

Geometric parameters (Å, º) top

C1—C2	1.519 (4)	C30—C34	1.395 (4)
C1—C5	1.526 (4)	C31—H31	0.9500
C1—C6	1.522 (4)	C31—C32	1.401 (4)
C1—N1	1.489 (4)	C32—C35	1.483 (4)
C2—C3	1.329 (4)	C32—N2	1.341 (4)
C2—C7	1.473 (4)	C33—C34	1.389 (4)
C3—H3	0.9500	C33—C40	1.496 (4)
C3—C4	1.498 (4)	C33—N2	1.346 (4)
C4—C8	1.526 (4)	C34—H34	0.9500
C4—C9	1.535 (4)	C35—C36	1.384 (4)
C4—N1	1.479 (4)	C35—N3	1.342 (4)
C5—H5A	0.9800	C36—H36	0.9500
C5—H5B	0.9800	C36—C37	1.389 (4)
C5—H5C	0.9800	C37—H37	0.9500
C6—H6A	0.9800	C37—C38	1.370 (4)
C6—H6B	0.9800	C38—H38	0.9500
C6—H6C	0.9800	C38—C39	1.382 (5)
C7—O2	1.203 (3)	C39—H39	0.9500
C7—O3	1.361 (3)	C39—N3	1.338 (4)
C8—H8A	0.9800	C40—C41	1.397 (4)
C8—H8B	0.9800	C40—N4	1.346 (4)
C8—H8C	0.9800	C41—H41	0.9500
C9—H9A	0.9800	C41—C42	1.385 (4)
C9—H9B	0.9800	C42—H42	0.9500
C9—H9C	0.9800	C42—C43	1.383 (4)
C10—C11	1.375 (4)	C43—H43	0.9500
C10—C15	1.367 (4)	C43—C44	1.382 (4)
C10—O3	1.413 (3)	C44—H44	0.9500
C11—H11	0.9500	C44—N4	1.339 (4)
C11—C12	1.381 (4)	C45—H45	0.9500
C12—H12	0.9500	C45—C46	1.371 (5)
C12—C13	1.394 (4)	C45—C50	1.370 (5)
C13—C14	1.399 (4)	C46—H46	0.9500
C13—C16	1.487 (4)	C46—C47	1.381 (6)
C14—H14	0.9500	C47—H47	0.9500
C14—C15	1.391 (4)	C47—C48	1.387 (6)
C15—H15	0.9500	C48—H48	0.9500
C16—C17	1.398 (4)	C48—C49	1.367 (6)
C16—C21	1.393 (4)	C49—H49	0.9500
C17—H17	0.9500	C49—C50	1.382 (5)
C17—C18	1.365 (4)	C50—H50	0.9500
C18—H18	0.9500	C51—H51	0.9500
C18—C19	1.396 (4)	C51—C52	1.3900
C19—C20	1.397 (4)	C51—C56	1.3900
C19—C22	1.437 (4)	C52—H52	0.9500
C20—H20	0.9500	C52—C53	1.3900
C20—C21	1.388 (4)	C53—H53	0.9500
C21—H21	0.9500	C53—C54	1.3900
C22—C23	1.195 (4)	C54—H54	0.9500
C23—C24	1.435 (4)	C54—C55	1.3900
C24—C25	1.405 (4)	C55—H55	0.9500
C24—C29	1.398 (4)	C55—C56	1.3900
C25—H25	0.9500	C56—H56	0.9500
C25—C26	1.384 (4)	C57—H57	0.9500
C26—H26	0.9500	C57—C58	1.370 (8)
C26—C27	1.399 (4)	C57—C59ⁱ	1.376 (8)
C27—C28	1.402 (4)	C58—H58	0.9500
C27—C30	1.489 (4)	C58—C59	1.376 (7)
C28—H28	0.9500	C59—C57ⁱ	1.376 (8)
C28—C29	1.383 (4)	C59—H59	0.9500
C29—H29	0.9500	N1—O1	1.274 (3)
C30—C31	1.398 (4)	O1—O1ⁱⁱ	4.004 (4)

C2—C1—C5	113.1 (2)	C28—C29—C24	120.7 (3)
C2—C1—C6	114.8 (2)	C28—C29—H29	119.6
C6—C1—C5	110.6 (2)	C31—C30—C27	121.5 (3)
N1—C1—C2	98.8 (2)	C34—C30—C27	121.0 (2)
N1—C1—C5	108.9 (2)	C34—C30—C31	117.4 (2)
N1—C1—C6	109.8 (2)	C30—C31—H31	120.4
C3—C2—C1	112.7 (2)	C30—C31—C32	119.2 (3)
C3—C2—C7	125.8 (3)	C32—C31—H31	120.4
C7—C2—C1	121.4 (2)	C31—C32—C35	120.5 (3)
C2—C3—H3	123.3	N2—C32—C31	123.3 (3)
C2—C3—C4	113.4 (3)	N2—C32—C35	116.2 (2)
C4—C3—H3	123.3	C34—C33—C40	120.2 (2)
C3—C4—C8	113.1 (2)	N2—C33—C34	123.6 (3)
C3—C4—C9	112.5 (2)	N2—C33—C40	116.2 (2)
C8—C4—C9	110.9 (2)	C30—C34—H34	120.3
N1—C4—C3	99.6 (2)	C33—C34—C30	119.4 (3)
N1—C4—C8	110.1 (2)	C33—C34—H34	120.3
N1—C4—C9	110.2 (2)	C36—C35—C32	121.6 (3)
C1—C5—H5A	109.5	N3—C35—C32	116.1 (2)
C1—C5—H5B	109.5	N3—C35—C36	122.3 (3)
C1—C5—H5C	109.5	C35—C36—H36	120.3
H5A—C5—H5B	109.5	C35—C36—C37	119.4 (3)
H5A—C5—H5C	109.5	C37—C36—H36	120.3
H5B—C5—H5C	109.5	C36—C37—H37	120.6
C1—C6—H6A	109.5	C38—C37—C36	118.9 (3)
C1—C6—H6B	109.5	C38—C37—H37	120.6
C1—C6—H6C	109.5	C37—C38—H38	120.9
H6A—C6—H6B	109.5	C37—C38—C39	118.1 (3)
H6A—C6—H6C	109.5	C39—C38—H38	120.9
H6B—C6—H6C	109.5	C38—C39—H39	117.9
O2—C7—C2	125.5 (3)	N3—C39—C38	124.2 (3)
O2—C7—O3	123.5 (3)	N3—C39—H39	117.9
O3—C7—C2	111.0 (2)	C41—C40—C33	121.0 (3)
C4—C8—H8A	109.5	N4—C40—C33	116.1 (2)
C4—C8—H8B	109.5	N4—C40—C41	122.9 (3)
C4—C8—H8C	109.5	C40—C41—H41	120.7
H8A—C8—H8B	109.5	C42—C41—C40	118.6 (3)
H8A—C8—H8C	109.5	C42—C41—H41	120.7
H8B—C8—H8C	109.5	C41—C42—H42	120.6
C4—C9—H9A	109.5	C43—C42—C41	118.8 (3)
C4—C9—H9B	109.5	C43—C42—H42	120.6
C4—C9—H9C	109.5	C42—C43—H43	120.7
H9A—C9—H9B	109.5	C44—C43—C42	118.7 (3)
H9A—C9—H9C	109.5	C44—C43—H43	120.7
H9B—C9—H9C	109.5	C43—C44—H44	118.0
C11—C10—O3	118.5 (3)	N4—C44—C43	123.9 (3)
C15—C10—C11	121.2 (3)	N4—C44—H44	118.0
C15—C10—O3	120.1 (3)	C46—C45—H45	120.2
C10—C11—H11	120.4	C50—C45—H45	120.2
C10—C11—C12	119.2 (3)	C50—C45—C46	119.7 (4)
C12—C11—H11	120.4	C45—C46—H46	119.7
C11—C12—H12	119.0	C45—C46—C47	120.5 (4)
C11—C12—C13	121.9 (3)	C47—C46—H46	119.7
C13—C12—H12	119.0	C46—C47—H47	120.3
C12—C13—C14	117.0 (3)	C46—C47—C48	119.5 (4)
C12—C13—C16	121.4 (3)	C48—C47—H47	120.3
C14—C13—C16	121.7 (3)	C47—C48—H48	120.1
C13—C14—H14	119.3	C49—C48—C47	119.9 (4)
C15—C14—C13	121.4 (3)	C49—C48—H48	120.1
C15—C14—H14	119.3	C48—C49—H49	120.0
C10—C15—C14	119.3 (3)	C48—C49—C50	120.0 (4)
C10—C15—H15	120.4	C50—C49—H49	120.0
C14—C15—H15	120.4	C45—C50—C49	120.4 (4)
C17—C16—C13	120.9 (3)	C45—C50—H50	119.8
C21—C16—C13	122.5 (3)	C49—C50—H50	119.8
C21—C16—C17	116.6 (3)	C52—C51—H51	120.0
C16—C17—H17	118.8	C52—C51—C56	120.0
C18—C17—C16	122.4 (3)	C56—C51—H51	120.0
C18—C17—H17	118.8	C51—C52—H52	120.0
C17—C18—H18	119.6	C51—C52—C53	120.0
C17—C18—C19	120.8 (3)	C53—C52—H52	120.0
C19—C18—H18	119.6	C52—C53—H53	120.0
C18—C19—C20	118.0 (3)	C54—C53—C52	120.0
C18—C19—C22	119.1 (3)	C54—C53—H53	120.0
C20—C19—C22	122.9 (3)	C53—C54—H54	120.0
C19—C20—H20	119.8	C55—C54—C53	120.0
C21—C20—C19	120.4 (3)	C55—C54—H54	120.0
C21—C20—H20	119.8	C54—C55—H55	120.0
C16—C21—H21	119.1	C54—C55—C56	120.0
C20—C21—C16	121.8 (3)	C56—C55—H55	120.0
C20—C21—H21	119.1	C51—C56—H56	120.0
C23—C22—C19	174.6 (3)	C55—C56—C51	120.0
C22—C23—C24	177.8 (3)	C55—C56—H56	120.0
C25—C24—C23	120.0 (3)	C58—C57—H57	119.6
C29—C24—C23	121.5 (3)	C58—C57—C59ⁱ	120.8 (5)
C29—C24—C25	118.5 (3)	C59ⁱ—C57—H57	119.6
C24—C25—H25	119.8	C57—C58—H58	120.1
C26—C25—C24	120.4 (3)	C57—C58—C59	119.8 (5)
C26—C25—H25	119.8	C59—C58—H58	120.1
C25—C26—H26	119.4	C57ⁱ—C59—H59	120.3
C25—C26—C27	121.2 (3)	C58—C59—C57ⁱ	119.4 (6)
C27—C26—H26	119.4	C58—C59—H59	120.3
C26—C27—C28	118.1 (3)	C4—N1—C1	115.5 (2)
C26—C27—C30	121.1 (3)	O1—N1—C1	122.4 (2)
C28—C27—C30	120.8 (3)	O1—N1—C4	122.1 (2)
C27—C28—H28	119.5	C32—N2—C33	117.1 (2)
C29—C28—C27	121.0 (3)	C39—N3—C35	117.2 (3)
C29—C28—H28	119.5	C44—N4—C40	117.0 (3)
C24—C29—H29	119.6	C7—O3—C10	116.5 (2)

C1—C2—C3—C4	−0.1 (3)	C27—C30—C31—C32	−175.1 (3)
C1—C2—C7—O2	−1.5 (4)	C27—C30—C34—C33	176.3 (3)
C1—C2—C7—O3	179.4 (2)	C28—C27—C30—C31	−158.0 (3)
C2—C1—N1—C4	−0.5 (3)	C28—C27—C30—C34	24.6 (4)
C2—C1—N1—O1	−179.4 (2)	C29—C24—C25—C26	0.2 (5)
C2—C3—C4—C8	116.6 (3)	C30—C27—C28—C29	−177.8 (3)
C2—C3—C4—C9	−116.8 (3)	C30—C31—C32—C35	177.0 (3)
C2—C3—C4—N1	−0.2 (3)	C30—C31—C32—N2	−2.0 (4)
C2—C7—O3—C10	168.2 (2)	C31—C30—C34—C33	−1.2 (4)
C3—C2—C7—O2	176.4 (3)	C31—C32—C35—C36	174.6 (3)
C3—C2—C7—O3	−2.6 (4)	C31—C32—C35—N3	−7.8 (4)
C3—C4—N1—C1	0.4 (3)	C31—C32—N2—C33	0.2 (4)
C3—C4—N1—O1	179.4 (2)	C32—C35—C36—C37	176.1 (3)
C5—C1—C2—C3	115.3 (3)	C32—C35—N3—C39	−175.8 (3)
C5—C1—C2—C7	−66.5 (3)	C33—C40—C41—C42	177.4 (3)
C5—C1—N1—C4	−118.7 (3)	C33—C40—N4—C44	−178.8 (3)
C5—C1—N1—O1	62.4 (3)	C34—C30—C31—C32	2.4 (4)
C6—C1—C2—C3	−116.4 (3)	C34—C33—C40—C41	164.3 (3)
C6—C1—C2—C7	61.8 (3)	C34—C33—C40—N4	−15.8 (4)
C6—C1—N1—C4	120.0 (3)	C34—C33—N2—C32	1.1 (4)
C6—C1—N1—O1	−58.9 (3)	C35—C32—N2—C33	−178.8 (2)
C7—C2—C3—C4	−178.2 (3)	C35—C36—C37—C38	−0.1 (5)
C8—C4—N1—C1	−118.6 (3)	C36—C35—N3—C39	1.8 (5)
C8—C4—N1—O1	60.4 (3)	C36—C37—C38—C39	1.2 (5)
C9—C4—N1—C1	118.8 (3)	C37—C38—C39—N3	−0.8 (5)
C9—C4—N1—O1	−62.3 (4)	C38—C39—N3—C35	−0.7 (5)
C10—C11—C12—C13	−0.6 (5)	C40—C33—C34—C30	−178.3 (3)
C11—C10—C15—C14	0.5 (5)	C40—C33—N2—C32	179.0 (2)
C11—C10—O3—C7	−80.9 (4)	C40—C41—C42—C43	2.1 (4)
C11—C12—C13—C14	1.5 (5)	C41—C40—N4—C44	1.1 (4)
C11—C12—C13—C16	−178.0 (3)	C41—C42—C43—C44	−0.4 (5)
C12—C13—C14—C15	−1.5 (5)	C42—C43—C44—N4	−1.1 (5)
C12—C13—C16—C17	−4.5 (5)	C43—C44—N4—C40	0.8 (5)
C12—C13—C16—C21	176.1 (3)	C45—C46—C47—C48	−0.9 (6)
C13—C14—C15—C10	0.5 (5)	C46—C45—C50—C49	−0.6 (5)
C13—C16—C17—C18	−178.4 (3)	C46—C47—C48—C49	0.0 (6)
C13—C16—C21—C20	178.4 (3)	C47—C48—C49—C50	0.6 (6)
C14—C13—C16—C17	176.0 (3)	C48—C49—C50—C45	−0.3 (5)
C14—C13—C16—C21	−3.4 (5)	C50—C45—C46—C47	1.2 (5)
C15—C10—C11—C12	−0.5 (5)	C51—C52—C53—C54	0.0
C15—C10—O3—C7	103.6 (3)	C52—C51—C56—C55	0.0
C16—C13—C14—C15	178.0 (3)	C52—C53—C54—C55	0.0
C16—C17—C18—C19	0.4 (5)	C53—C54—C55—C56	0.0
C17—C16—C21—C20	−1.0 (5)	C54—C55—C56—C51	0.0
C17—C18—C19—C20	−1.8 (5)	C56—C51—C52—C53	0.0
C17—C18—C19—C22	176.8 (3)	C57—C58—C59—C57ⁱ	−0.5 (8)
C18—C19—C20—C21	1.8 (5)	C59ⁱ—C57—C58—C59	0.5 (8)
C19—C20—C21—C16	−0.4 (5)	N1—C1—C2—C3	0.4 (3)
C21—C16—C17—C18	1.0 (5)	N1—C1—C2—C7	178.5 (2)
C22—C19—C20—C21	−176.7 (3)	N2—C32—C35—C36	−6.4 (4)
C23—C24—C25—C26	−179.5 (3)	N2—C32—C35—N3	171.3 (3)
C23—C24—C29—C28	178.9 (3)	N2—C33—C34—C30	−0.5 (4)
C24—C25—C26—C27	1.0 (5)	N2—C33—C40—C41	−13.7 (4)
C25—C24—C29—C28	−0.8 (4)	N2—C33—C40—N4	166.2 (2)
C25—C26—C27—C28	−1.5 (4)	N3—C35—C36—C37	−1.5 (5)
C25—C26—C27—C30	177.1 (3)	N4—C40—C41—C42	−2.5 (4)
C26—C27—C28—C29	0.9 (4)	O2—C7—O3—C10	−10.8 (4)
C26—C27—C30—C31	23.4 (4)	O3—C10—C11—C12	−175.9 (3)
C26—C27—C30—C34	−154.0 (3)	O3—C10—C15—C14	175.9 (3)
C27—C28—C29—C24	0.3 (4)

Symmetry codes: (i) −x+3, −y, −z+1; (ii) −x, −y, −z.

Hydrogen-bond geometry (Å, º) top

Cg4, Cg7 and Cg10 are the centroids of pyridine ring N4/C40–C44, spacer ring C24–C29 and benzene ring C54–C59, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C37—H37···O1ⁱⁱⁱ	0.95	2.65	3.228 (4)	120
C38—H38···O2^iv	0.95	2.55	3.485 (4)	169
C6—H6C···O1ⁱⁱ	0.98	2.61	3.499 (4)	151
C9—H9B···Cg4^v	0.96	2.79	3.602 (4)	140
C14—H14···Cg10^vi	0.95	2.88	3.608 (4)	134
C14—H14···Cg10^vii	0.95	2.88	3.608 (4)	134
C55—H55···Cg7^viii	0.95	2.90	3.680 (3)	140

Symmetry codes: (ii) −x, −y, −z; (iii) x+3, y+1, z+1; (iv) −x+4, −y+1, −z+1; (v) x−2, y−1, z−1; (vi) x−1, y, z; (vii) −x+2, −y, −z+1; (viii) −x+3, −y+1, −z+1.

Hydrogen-bond geometry (Å, º) top

Cg4, Cg7 and Cg10 are the centroids of pyridine ring N4/C40–C44, spacer ring C24–C29 and benzene ring C54–C59, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C37—H37···O1ⁱ	0.95	2.65	3.228 (4)	120
C38—H38···O2ⁱⁱ	0.95	2.55	3.485 (4)	169
C6—H6C···O1ⁱⁱⁱ	0.98	2.61	3.499 (4)	151
C9—H9B···Cg4^iv	0.96	2.79	3.602 (4)	140
C14—H14···Cg10^v	0.95	2.88	3.608 (4)	134
C14—H14···Cg10^vi	0.95	2.88	3.608 (4)	134
C55—H55···Cg7^vii	0.95	2.90	3.680 (3)	140

Symmetry codes: (i) x+3, y+1, z+1; (ii) −x+4, −y+1, −z+1; (iii) −x, −y, −z; (iv) x−2, y−1, z−1; (v) x−1, y, z; (vi) −x+2, −y, −z+1; (vii) −x+3, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	C₄₄H₃₅N₄O₃·2.5C₆H₆
M_r	863.03
Crystal system, space group	Triclinic, P1
Temperature (K)	123
a, b, c (Å)	5.7578 (1), 18.0559 (4), 23.3716 (6)
α, β, γ (°)	105.5870 (13), 93.7408 (13), 92.6002 (14)
V (Å³)	2330.41 (9)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.28 × 0.20 × 0.08

Data collection
Diffractometer	Nonius KappaCCD diffractometer
Absorption correction	Multi-scan (SORTAV; Blessing, 1995)
T_min, T_max	0.808, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	74528, 11227, 6356
R_int	0.109
(sin θ/λ)_max (Å⁻¹)	0.661

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.071, 0.217, 1.07
No. of reflections	11227
No. of parameters	587
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.33, −0.27

Computer programs: HKL DENZO and SCALEPACK (Otwinowski & Minor 1997), HKL SCALEPACK (Otwinowski & Minor 1997), SHELXS97 (Sheldrick,2008), SHELXL2013 (Sheldrick, 2015), Olex2 (Dolomanov et al., 2009) and Mercury (Macrae et al., 2008), Olex2 (Dolomanov et al., 2009).

Acknowledgements

The authors thank Professor Dr. A. C. Filippou for providing the X-ray infrastructure. OS thanks the DFG for funding via SFB 813.

References

Ackermann, K., Giannoulis, A., Cordes, D. B., Slawin, A. M. Z. & Bode, B. E. (2015). Chem. Commun. 51, 5257–5260. Web of Science CSD CrossRef CAS Google Scholar
Bessel, C. A., See, R. F., Jameson, D. L., Churchill, M. R. & Takeuchi, K. J. (1992). J. Chem. Soc. Dalton Trans. pp. 3223–3228. CSD CrossRef Web of Science Google Scholar
Blessing, R. H. (1995). Acta Cryst. A51, 33–38. CrossRef CAS Web of Science IUCr Journals Google Scholar
Bode, E. B., Plackmeyer, J., Prisner, T. F. & Schiemann, O. (2008). J. Phys. Chem. A, 112, 5064–5073. CrossRef PubMed CAS Google Scholar
Constable, E. C., Baum, G., Bill, E., Dyson, R., van Eldik, R., Fenske, D., Kaderli, D., Morris, D., Neubrand, A., Neuburger, M., Smith, D. R., Wieghardt, K., Zehnder, M. & Zuberbühler, A. D. (1999). Chem. Eur. J. 5, 498–508. CrossRef CAS Google Scholar
Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339–341. Web of Science CrossRef CAS IUCr Journals Google Scholar
Eryazici, I., Moorefield, C. N., Durmus, S. & Newkome, G. R. (2006). J. Org. Chem. 71, 1009–1014. Web of Science CSD CrossRef PubMed CAS Google Scholar
Fallahpour, R.-A., Neuburger, M. & Zehnder, M. (1999). Polyhedron, 18, 2445–2454. Web of Science CSD CrossRef CAS Google Scholar
Fey, T., Fischer, H., Bachmann, S., Albert, K. & Bolm, C. (2001). J. Org. Chem. 66, 8154–8159. CrossRef PubMed CAS Google Scholar
Fink, D. W. & Ohnesorge, W. E. (1970). J. Phys. Chem. 74, 72–77. CrossRef CAS Google Scholar
Folgado, J. V., Henke, W., Allmann, R., Stratemeier, H., Beltrán-Porter, D., Rojo, T. & Reinen, D. (1990). Inorg. Chem. 29, 2035–2042. CSD CrossRef CAS Web of Science Google Scholar
Fritscher, J., Beyer, M. & Schiemann, O. (2002). Chem. Phys. Lett. 364, 393–401. Web of Science CSD CrossRef CAS Google Scholar
Grave, C., Lentz, D., Schäfer, A., Samorì, P., Rabe, P. J., Franke, P. & Schlüter, A. D. (2003). J. Am. Chem. Soc. 125, 6907–6918. Web of Science CSD CrossRef PubMed CAS Google Scholar
Groom, C. R. & Allen, F. H. (2014). Angew. Chem. Int. Ed. 53, 662–671. Web of Science CSD CrossRef CAS Google Scholar
Grosshenny, V. & Ziessel, R. (1993). J. Organomet. Chem. 453, C19–C22. CrossRef CAS Google Scholar
Hogg, R. & Wilkins, R. G. (1962). J. Chem. Soc. pp. 341–350. CrossRef Web of Science Google Scholar
Hoover, J. M. & Stahl, S. S. (2011). J. Am. Chem. Soc. 133, 16901–16910. CrossRef CAS PubMed Google Scholar
Janiak, C. (2000). J. Chem. Soc. Dalton Trans. pp. 3885–3896. Web of Science CrossRef Google Scholar
Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466–470. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Margraf, D., Schuetz, D., Prisner, T. F. & Bats, J. W. (2009). Acta Cryst. E65, o1784. Web of Science CSD CrossRef IUCr Journals Google Scholar
Meyer, A., Schnakenburg, G., Glaum, R. & Schiemann, O. (2015b). Inorg. Chem. 54, 8456–8464. CrossRef CAS PubMed Google Scholar
Meyer, A., Wiecek, J., Schnakenburg, G. & Schiemann, O. (2015a). Acta Cryst. E71, 870–874. CSD CrossRef IUCr Journals Google Scholar
Murguly, E., Norsten, T. B. & Branda, N. (1999). J. Chem. Soc. Perkin Trans. 2, pp. 2789–2794. Web of Science CSD CrossRef Google Scholar
Nakamoto, K. (1960). J. Phys. Chem. 64, 1420–1425. CrossRef CAS Web of Science Google Scholar
Narr, E., Godt, A. & Jeschke, G. (2002). Angew. Chem. Int. Ed. 41, 3907–3910. CrossRef CAS Google Scholar
Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307–326. New York: Academic Press. Google Scholar
Rajca, A., Mukherjee, S., Pink, M. & Rajca, S. (2006). J. Am. Chem. Soc. 128, 13497–13507. Web of Science CSD CrossRef PubMed CAS Google Scholar
Reginsson, G. W. & Schiemann, O. (2011). Biochem. Soc. Trans. 39, 128–139. Web of Science CrossRef CAS PubMed Google Scholar
Schuetz, D., Margraf, D., Prisner, T. F. & Bats, J. W. (2010). Acta Cryst. E66, o729–o730. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Sheldrick, G. M. (2015). Acta Cryst. C71, 3–8. Web of Science CrossRef IUCr Journals Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 71| Part 10| October 2015| Pages 1245-1249

doi:10.1107/S2056989015017697

Open

access

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Search IUCr Journals		doi		Advanced search
Author		volume	page

research communications\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Crystal structure of 4′-{[4-(2,2′:6′,2′′-terpyrid­yl-4′-yl)phen­yl]ethyn­yl}bi­phenyl-4-yl (2,2,5,5-tetra­methyl-1-oxyl-3-pyrrolin-3-yl)formate benzene 2.5-solvate

1. Chemical context

2. Structural commentary

3. Supra­molecular features

4. Database survey

5. Synthesis and crystallization

6. Refinement

Supporting information

Acknowledgements

References

research communications

Crystal structure of 4′-{[4-(2,2′:6′,2′′-terpyridyl-4′-yl)phenyl]ethynyl}biphenyl-4-yl (2,2,5,5-tetramethyl-1-oxyl-3-pyrrolin-3-yl)formate benzene 2.5-solvate

3. Supramolecular features