research communications
of 2,6-diaminopyridinium chloride
aInstitute of Applied Synthetic Chemistry, TU Wien, Getreidemarkt 9/163, A-1060 Vienna, Austria, and bInstitute for Chemical Technologies and Analytics, Division of Structural Chemistry, TU Wien, Getreidemarkt 9/164-SC, A-1060 Vienna, Austria
*Correspondence e-mail: Matthias.Weil@tuwien.ac.at
The 5H8N3+·Cl−, comprises one half of the 2,6-diaminopyridinium cation (the other half being completed by the application of mirror symmetry) and one Cl− counter-anion, also located on the mirror plane. The amino N atom shows a significant pyramidalization, with a dihedral angle of 30.4 (14)° between the least-squares planes of the amino group and the non-H atoms of the 2,6-diaminopyridinium moiety. In the crystal, the cationic molecules and Cl− counter-anions are arranged in sheets parallel to (001) consisting of alternating polar and non-polar parts associated with the the Cl− anions, pyridinium and amino moieties, and the pyridine rings, respectively. N—H⋯Cl interactions within the polar part, as well as slipped π–π interactions in the non-polar part, help to establish the three-dimensional network.
of the title salt, CCCDC reference: 1452262
1. Chemical context
Pincer compounds are an important class of chelating ligands, and their metal complexes have attracted tremendous interest due to their high stability, activity, variability and applicability in organic synthesis and catalysis (Szabo & Wendt, 2014). Whereas a plethora of (mostly) precious transition-metal pincer complexes has been reported, information on group 6 pincer complexes is rather scarce. During a project aimed at the preparation and characterization of group 6 PNP pincer compounds (Öztopcu et al., 2013; de Aguiar et al., 2014; Mastalir et al., 2016), crystals of the title salt, C5H8N3+·Cl−, were obtained accidentally through hydrolysis of the employed ligand N,N'-bis(diisopropylphosphino)-2,6-diaminopyridine in the presence of CrCl3·6H2O. Here we report on the of this salt.
2. Structural commentary
The cation of the title structure is protonated at the pyridine N atom (Fig. 1). The comprises half a molecule of the 2,6-diaminopyridinium cation, with a mirror plane running through the pyridinium group (N1—H1N1) and the para-C—H group (C3—H1C3); the Cl− anion is also located on the mirror plane. In agreement with other 2,6-diaminopyridinium cations, the C—N(H)+—C angle involving the pyridinium group is enlarged [C1—N1—C1i = 123.37 (8)°; symmetry code: (i) x, −y, z] whereas the angle between the pyridinium N atom and the C atom in the ortho position (bearing the amino group) and in the meta position is reduced [N1—C1—C2 = 118.83 (6)°]. This situation is reversed in 2,6-diaminopyridine due to the non-protonated ring N atom in this structure (Schwalbe et al., 1987). A common feature of the non-protonated 2,6-diaminopyridine molecule and the 2,6-diaminopyridinium cation is a significant pyramidalization of the amino N atom. In the title structure, the bond angle sum at this atom (N2) deviates with 349.0° clearly from the expected 360° for an ideal trigonal–planar group. The pyramidalization is also reflected by the dihedral angle of 30.4 (14)° between the least-squares planes of the amino group and the non-H atoms of the 2,6-diaminopyridinium moiety.
3. Supramolecular features
The pyridinium N1—H1N1 group is the donor of a nearly linear hydrogen bond to the Cl− counter anion (Table 1). The amino group also participates in the formation of N—H⋯Cl hydrogen bonds, albeit of explicit weaker nature. One hydrogen atom (H2N2) is clearly involved in hydrogen bonding with an H2N2⋯Cl1 distance of 2.63 Å and an N2—H2N2⋯Cl1 angle of 157°. Although the D⋯A contact involving the second hydrogen atom, H2N2, is 0.04 Å shorter than that of the other hydrogen bond of this group, the comparatively long H1N2⋯Cl distance of 2.88 Å and the very small N2—H1N2⋯Cl1 angle of 117° give room for interpretation whether or not this is a real hydrogen bond.
In the crystal (Figs. 2 and 3), the cationic molecules and anions are arranged into layers with alternating polar and non-polar parts extending parallel to (001). Adjacent polar parts, comprising the Cl− anions and the pyridinium and amino moieties, are linked through N—H⋯Cl hydrogen bonds into sheets with a thickness of ≃ c/2. The non-polar parts, i.e. the pyridine rings, interact through slipped π–π stacking along [001] with a centroid-to-centroid distance of 3.5129 (6) Å; the corresponding plane-to-plane distance between the pyridine rings is 3.344 Å.
4. Database survey
A search in the CSD (Groom & Allen, 2014; CSD Version 5.31) revealed 87 different salts containing the 2,6-diaminopyridinium cation, with the majority of cases in the form of organic anions (46 representatives), followed by complex metal anions (31 representatives). Two structures are reported that contain additional metal cations and inorganic anions, and eight representatives are compiled with inorganic anions only, including the SiF62− salt (CSD code FOSXER; Gelmboldt et al., 2009), the Br− salt (GOLMIF; Turrell et al., 2010), the BF4− salt (IFOQAW; Benito-Garagorri et al.; 2007), the Br− salt monohydrate (ILINEW; Haddad & Al-Far, 2003), the hydrogensulfate sulfate salt (KORRAM; Said & Naili, 2014), the ClO4− salt (MIGWOP; Jazdoń et al., 2007), the H2PO4− salt (QEDHUE; Yu, 2012) and the NO3− salt (XAKVAG; Kristiansson, 2000). It should be noted that the chemically most related anhydrous Br− salt crystallizes in I2d and hence shows no isotypism with the title Cl− salt.
5. Synthesis and crystallization
N,N'-bis(diisopropylphosphino)-2,6-diaminopyridine (0.2 g, 0.53 mmol) was dissolved in dry tetrahydrofuran (5 ml) under argon atmosphere. CrCl3·6H2O (0.134 g, 0.51 mmol) was added and the resulting mixture stirred for 4 h at room temperature. The formed purple solid was filtered off, washed with dry diethyl ether and dried. The solid was redissolved in acetonitrile for crystallization initiated by solvent diffusion with diethyl ether. The title compound grew in the form of yellow crystals as the only solid product. We assume that the CrCl3 in combination with water is able to cleave the P—N bond of the pincer compound accompanied by an in situ formation of HCl which eventually yields the title compound.
6. Refinement
All H atoms were clearly discernible from difference Fourier maps and were refined freely. Crystal data, data collection and structure .
details are summarized in Table 2
|
Supporting information
CCDC reference: 1452262
10.1107/S2056989016002425/hb7564sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S2056989016002425/hb7564Isup2.hkl
Supporting information file. DOI: 10.1107/S2056989016002425/hb7564Isup3.cml
Pincer compounds are an important class of chelating ligands, and their metal complexes have attracted tremendous interest due to their high stability, activity, variability and applicability in organic synthesis and catalysis (Szabo & Wendt, 2014). Whereas a plethora of (mostly) precious transition-metal pincer complexes has been reported, information on group 6 pincer complexes is rather scarce. During a project aimed at the preparation and characterization of group 6 PNP pincer compounds (Öztopcu et al., 2013; de Aguiar et al., 2014; Mastalir et al., 2016), crystals of the title salt, C5H8N3+·Cl−, were obtained accidentally through hydrolysis of the employed ligand N,N'-bis(diisopropylphosphino)-2,6-diaminopyridine in the presence of CrCl3·6H2O. Here we report on the
of this salt.The cation of the title structure is protonated at the pyridine N atom (Fig. 1). The
comprises half a molecule of the 2,6-diaminopyridinium cation, with a mirror plane running through the pyridinium group (N1—H1N1) and the para-C—H group (C3—H1C3); the Cl− anion is also located on the mirror plane. In agreement with other 2,6-diaminopyridinium cations, the C—N(H)+—C angle involving the pyridinium group is enlarged [C1—N1—C1i = 123.37 (8)°; symmetry code: (i) x, −y, z] whereas the angle between the pyridinium N atom and the C atom in the ortho position (bearing the amino group) and in the meta position is reduced [N1—C1—C2 = 118.83 (6)°]. This situation is reversed in 2,6-diaminopyridine due to the non-protonated ring N atom in this structure (Schwalbe et al., 1987). A common feature of the non-protonated 2,6-diaminopyridine molecule and the 2,6-diaminopyridinium cation is a significant pyramidalization of the amino N atom. In the title structure, the bond angle sum at this atom (N2) deviates with 349.0° clearly from the expected 360° for an ideal trigonal–planar group. The pyramidalization is also reflected by the dihedral angle of 30.4 (14)° between the least-squares planes of the amino group and the non-H atoms of the 2,6-diaminopyridinium moiety.The pyridinium N1—H1N1 group is the donor of a nearly linear hydrogen bond to the Cl− counter anion (Table 1). The amino group also participates in the formation of N—H···Cl hydrogen bonds, albeit of explicit weaker nature. One hydrogen atom (H2N2) is clearly involved in hydrogen bonding with an H2N2···Cl1 distance of 2.63 Å and an N2—H2N2···Cl1 angle of 157°. Although the D···A contact involving the second hydrogen atom, H2N2, is 0.04 Å shorter than that of the other hydrogen bond of this group, the comparatively long H1N2···Cl distance of 2.88 Å and the very small N2—H1N2···Cl1 angle of 117° give room for interpretation whether or not this is a real hydrogen bond.
In the crystal (Figs. 2 and 3), the cationic molecules and anions are arranged into layers with alternating polar and non-polar parts extending parallel to (001). Adjacent polar parts, comprising the Cl− anions and the pyridinium and amino moieties, are linked through N—H···Cl hydrogen bonds into sheets with a thickness of ≈ c/2. The non-polar parts, i.e. the pyridine rings, interact through slipped π–π stacking along [001] with a centroid-to-centroid distance of 3.5129 (6) Å; the corresponding plane-to-plane distance between the pyridine rings is 3.344 Å.
A search in the CSD (Groom & Allen, 2014; CSD Version 5.31) revealed 87 different salts containing the 2,6-diaminopyridinium cation, with the majority of cases in the form of organic anions (46 representatives), followed by complex metal anions (31 representatives). Two structures are reported that contain additional metal cations and inorganic anions, and eight representatives are compiled with inorganic anions only, including the SiF62− salt (CSD code FOSXER; Gelmboldt et al., 2009), the Br− salt (GOLMIF; Turrell et al., 2010), the BF4− salt (IFOQAW; Benito-Garagorri et al.; 2007), the Br− salt monohydrate (ILINEW; Haddad & Al-Far, 2003), the hydrogensulfate sulfate salt (KORRAM; Said & Naili, 2014), the ClO4− salt (MIGWOP; Jazdoń et al., 2007), the H2PO4− salt (QEDHUE; Yu, 2012) and the NO3− salt (XAKVAG; Kristiansson, 2000). It should be noted that the chemically most related anhydrous Br− salt crystallizes in 42d and hence shows no isotypism with the title Cl− salt.
IN,N'-bis(diisopropylphosphino)-2,6-diaminopyridine (0.2 g, 0.53 mmol) was dissolved in dry tetrahydrofuran (5 ml) under argon atmosphere. CrCl3·6H2O (0.134 g, 0.51 mmol) was added and the resulting mixture stirred for 4 h at room temperature. The formed purple solid was filtered off, washed with dry diethyl ether and dried. The solid was redissolved in acetonitrile for crystallization initiated by solvent diffusion with diethyl ether. The title compound grew in form of yellow crystals as the only solid product. We assume that the
CrCl3 in combination with water is able to cleave the P—N bond of the pincer compound accompanied by an in situ formation of HCl which eventually yields the title compound.Pincer compounds are an important class of chelating ligands, and their metal complexes have attracted tremendous interest due to their high stability, activity, variability and applicability in organic synthesis and catalysis (Szabo & Wendt, 2014). Whereas a plethora of (mostly) precious transition-metal pincer complexes has been reported, information on group 6 pincer complexes is rather scarce. During a project aimed at the preparation and characterization of group 6 PNP pincer compounds (Öztopcu et al., 2013; de Aguiar et al., 2014; Mastalir et al., 2016), crystals of the title salt, C5H8N3+·Cl−, were obtained accidentally through hydrolysis of the employed ligand N,N'-bis(diisopropylphosphino)-2,6-diaminopyridine in the presence of CrCl3·6H2O. Here we report on the
of this salt.The cation of the title structure is protonated at the pyridine N atom (Fig. 1). The
comprises half a molecule of the 2,6-diaminopyridinium cation, with a mirror plane running through the pyridinium group (N1—H1N1) and the para-C—H group (C3—H1C3); the Cl− anion is also located on the mirror plane. In agreement with other 2,6-diaminopyridinium cations, the C—N(H)+—C angle involving the pyridinium group is enlarged [C1—N1—C1i = 123.37 (8)°; symmetry code: (i) x, −y, z] whereas the angle between the pyridinium N atom and the C atom in the ortho position (bearing the amino group) and in the meta position is reduced [N1—C1—C2 = 118.83 (6)°]. This situation is reversed in 2,6-diaminopyridine due to the non-protonated ring N atom in this structure (Schwalbe et al., 1987). A common feature of the non-protonated 2,6-diaminopyridine molecule and the 2,6-diaminopyridinium cation is a significant pyramidalization of the amino N atom. In the title structure, the bond angle sum at this atom (N2) deviates with 349.0° clearly from the expected 360° for an ideal trigonal–planar group. The pyramidalization is also reflected by the dihedral angle of 30.4 (14)° between the least-squares planes of the amino group and the non-H atoms of the 2,6-diaminopyridinium moiety.The pyridinium N1—H1N1 group is the donor of a nearly linear hydrogen bond to the Cl− counter anion (Table 1). The amino group also participates in the formation of N—H···Cl hydrogen bonds, albeit of explicit weaker nature. One hydrogen atom (H2N2) is clearly involved in hydrogen bonding with an H2N2···Cl1 distance of 2.63 Å and an N2—H2N2···Cl1 angle of 157°. Although the D···A contact involving the second hydrogen atom, H2N2, is 0.04 Å shorter than that of the other hydrogen bond of this group, the comparatively long H1N2···Cl distance of 2.88 Å and the very small N2—H1N2···Cl1 angle of 117° give room for interpretation whether or not this is a real hydrogen bond.
In the crystal (Figs. 2 and 3), the cationic molecules and anions are arranged into layers with alternating polar and non-polar parts extending parallel to (001). Adjacent polar parts, comprising the Cl− anions and the pyridinium and amino moieties, are linked through N—H···Cl hydrogen bonds into sheets with a thickness of ≈ c/2. The non-polar parts, i.e. the pyridine rings, interact through slipped π–π stacking along [001] with a centroid-to-centroid distance of 3.5129 (6) Å; the corresponding plane-to-plane distance between the pyridine rings is 3.344 Å.
A search in the CSD (Groom & Allen, 2014; CSD Version 5.31) revealed 87 different salts containing the 2,6-diaminopyridinium cation, with the majority of cases in the form of organic anions (46 representatives), followed by complex metal anions (31 representatives). Two structures are reported that contain additional metal cations and inorganic anions, and eight representatives are compiled with inorganic anions only, including the SiF62− salt (CSD code FOSXER; Gelmboldt et al., 2009), the Br− salt (GOLMIF; Turrell et al., 2010), the BF4− salt (IFOQAW; Benito-Garagorri et al.; 2007), the Br− salt monohydrate (ILINEW; Haddad & Al-Far, 2003), the hydrogensulfate sulfate salt (KORRAM; Said & Naili, 2014), the ClO4− salt (MIGWOP; Jazdoń et al., 2007), the H2PO4− salt (QEDHUE; Yu, 2012) and the NO3− salt (XAKVAG; Kristiansson, 2000). It should be noted that the chemically most related anhydrous Br− salt crystallizes in 42d and hence shows no isotypism with the title Cl− salt.
IN,N'-bis(diisopropylphosphino)-2,6-diaminopyridine (0.2 g, 0.53 mmol) was dissolved in dry tetrahydrofuran (5 ml) under argon atmosphere. CrCl3·6H2O (0.134 g, 0.51 mmol) was added and the resulting mixture stirred for 4 h at room temperature. The formed purple solid was filtered off, washed with dry diethyl ether and dried. The solid was redissolved in acetonitrile for crystallization initiated by solvent diffusion with diethyl ether. The title compound grew in form of yellow crystals as the only solid product. We assume that the
CrCl3 in combination with water is able to cleave the P—N bond of the pincer compound accompanied by an in situ formation of HCl which eventually yields the title compound. detailsAll H atoms were clearly discernible from difference maps and were refined freely. Crystal data, data collection and structure
details are summarized in Table 2.Data collection: APEX2 (Bruker, 2014); cell
SAINT (Bruker, 2014); data reduction: SAINT (Bruker, 2014); program(s) used to solve structure: SUPERFLIP (Palatinus & Chapuis, 2007); program(s) used to refine structure: JANA2006 (Petříček et al., 2014); molecular graphics: XP in SHELXTL (Sheldrick, 2008) and Mercury (Macrae et al., 2006); software used to prepare material for publication: publCIF (Westrip, 2010).Fig. 1. The molecular structure of the cation and the inorganic anion in the title structure. Displacement ellipsoids are drawn at the 50% probability level. [Symmetry code: (i) x, −y, z.] | |
Fig. 2. Crystal packing of the organic and inorganic components in the title structure in a projection along [001]. N—H···Cl hydrogen bonds involving the pyridinium group are shown as magenta dotted lines and those involving the amino group are shown as orange dotted lines. | |
Fig. 3. Crystal packing of the organic and inorganic components in the title structure in a projection along [100]. The colour code of the intermolecular interactions is as in Fig. 2. |
C5H8N3+·Cl− | F(000) = 304 |
Mr = 145.6 | Dx = 1.462 Mg m−3 |
Monoclinic, C2/m | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -C 2y | Cell parameters from 6316 reflections |
a = 10.8046 (10) Å | θ = 2.9–35.5° |
b = 9.0459 (9) Å | µ = 0.48 mm−1 |
c = 6.8108 (7) Å | T = 100 K |
β = 96.710 (2)° | Block, yellow |
V = 661.11 (11) Å3 | 0.52 × 0.38 × 0.23 mm |
Z = 4 |
Bruker Kappa APEXII CCD diffractometer | 1538 independent reflections |
Radiation source: X-ray tube | 1407 reflections with I > 3σ(I) |
Graphite monochromator | Rint = 0.031 |
ω– and φ–scans | θmax = 35.0°, θmin = 3.0° |
Absorption correction: multi-scan (SADABS; Bruker, 2014) | h = −17→17 |
Tmin = 0.80, Tmax = 0.90 | k = −14→14 |
9529 measured reflections | l = −10→10 |
Refinement on F | 0 constraints |
R[F2 > 2σ(F2)] = 0.024 | All H-atom parameters refined |
wR(F2) = 0.038 | Weighting scheme based on measured s.u.'s w = 1/(σ2(F) + 0.0001F2) |
S = 2.24 | (Δ/σ)max = 0.030 |
1538 reflections | Δρmax = 0.49 e Å−3 |
64 parameters | Δρmin = −0.18 e Å−3 |
0 restraints |
C5H8N3+·Cl− | V = 661.11 (11) Å3 |
Mr = 145.6 | Z = 4 |
Monoclinic, C2/m | Mo Kα radiation |
a = 10.8046 (10) Å | µ = 0.48 mm−1 |
b = 9.0459 (9) Å | T = 100 K |
c = 6.8108 (7) Å | 0.52 × 0.38 × 0.23 mm |
β = 96.710 (2)° |
Bruker Kappa APEXII CCD diffractometer | 1538 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2014) | 1407 reflections with I > 3σ(I) |
Tmin = 0.80, Tmax = 0.90 | Rint = 0.031 |
9529 measured reflections |
R[F2 > 2σ(F2)] = 0.024 | 0 restraints |
wR(F2) = 0.038 | All H-atom parameters refined |
S = 2.24 | Δρmax = 0.49 e Å−3 |
1538 reflections | Δρmin = −0.18 e Å−3 |
64 parameters |
x | y | z | Uiso*/Ueq | ||
Cl1 | 0.17115 (2) | 0 | 0.12206 (3) | 0.01401 (7) | |
N1 | 0.45600 (9) | 0 | 0.22925 (12) | 0.0132 (2) | |
N2 | 0.44617 (7) | 0.25682 (8) | 0.22357 (10) | 0.01951 (18) | |
C1 | 0.51532 (7) | 0.13257 (7) | 0.25660 (9) | 0.01272 (16) | |
C2 | 0.64225 (7) | 0.13396 (7) | 0.32011 (10) | 0.01334 (17) | |
C3 | 0.70393 (10) | 0 | 0.35111 (14) | 0.0136 (2) | |
H1C2 | 0.6796 (9) | 0.2256 (14) | 0.3421 (16) | 0.019 (3)* | |
H1C3 | 0.7905 (16) | 0 | 0.392 (2) | 0.015 (3)* | |
H1N2 | 0.3742 (16) | 0.2574 (17) | 0.150 (2) | 0.046 (4)* | |
H2N2 | 0.4841 (12) | 0.3350 (15) | 0.2058 (19) | 0.032 (3)* | |
H1N1 | 0.3735 (19) | 0 | 0.191 (3) | 0.039 (5)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.01121 (13) | 0.01270 (11) | 0.01763 (12) | 0 | −0.00037 (8) | 0 |
N1 | 0.0093 (4) | 0.0176 (4) | 0.0128 (3) | 0 | 0.0018 (3) | 0 |
N2 | 0.0192 (3) | 0.0187 (3) | 0.0214 (3) | 0.0075 (2) | 0.0056 (2) | 0.0065 (2) |
C1 | 0.0137 (3) | 0.0143 (3) | 0.0107 (2) | 0.0025 (2) | 0.0039 (2) | 0.00180 (19) |
C2 | 0.0136 (3) | 0.0118 (3) | 0.0149 (3) | −0.0012 (2) | 0.0026 (2) | −0.00027 (19) |
C3 | 0.0108 (4) | 0.0154 (4) | 0.0145 (4) | 0 | 0.0011 (3) | 0 |
N1—C1 | 1.3622 (8) | C1—C2 | 1.3890 (10) |
N1—C1 | 1.3622 (8) | C2—C3 | 1.3872 (9) |
N1—H1N1 | 0.90 (2) | C2—H1C2 | 0.927 (12) |
N2—C1 | 1.3538 (10) | C3—H1C3 | 0.944 (17) |
N2—H1N2 | 0.875 (16) | C3—C2 | 1.3872 (9) |
N2—H2N2 | 0.833 (13) | ||
C1—N1—C1 | 123.37 (8) | N2—C1—C2 | 123.35 (6) |
C1—N1—H1N1 | 118.32 (4) | C1—C2—C3 | 118.60 (7) |
C1—N1—H1N1 | 118.32 (4) | C1—C2—H1C2 | 117.0 (6) |
C1—N2—H1N2 | 122.5 (10) | C3—C2—H1C2 | 124.4 (6) |
C1—N2—H2N2 | 117.2 (9) | C2—C3—C2 | 121.75 (9) |
H1N2—N2—H2N2 | 109.3 (13) | C2—C3—H1C3 | 119.12 (5) |
N1—C1—N2 | 117.81 (7) | C2—C3—H1C3 | 119.12 (5) |
N1—C1—C2 | 118.83 (6) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1N1···Cl1 | 0.90 (2) | 2.18 (2) | 3.0790 (11) | 175.6 (19) |
N2—H2N2···Cl1i | 0.833 (13) | 2.628 (13) | 3.4086 (8) | 156.5 (12) |
N2—H1N2···Cl1ii | 0.875 (13) | 2.877 (13) | 3.3601 (8) | 116.8 (2) |
Symmetry codes: (i) x+1/2, y+1/2, z; (ii) −x+1/2, −y+1/2, −z. |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1N1···Cl1 | 0.90 (2) | 2.18 (2) | 3.0790 (11) | 175.6 (19) |
N2—H2N2···Cl1i | 0.833 (13) | 2.628 (13) | 3.4086 (8) | 156.5 (12) |
N2—H1N2···Cl1ii | 0.875 (13) | 2.877 (13) | 3.3601 (8) | 116.8 (2) |
Symmetry codes: (i) x+1/2, y+1/2, z; (ii) −x+1/2, −y+1/2, −z. |
Experimental details
Crystal data | |
Chemical formula | C5H8N3+·Cl− |
Mr | 145.6 |
Crystal system, space group | Monoclinic, C2/m |
Temperature (K) | 100 |
a, b, c (Å) | 10.8046 (10), 9.0459 (9), 6.8108 (7) |
β (°) | 96.710 (2) |
V (Å3) | 661.11 (11) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.48 |
Crystal size (mm) | 0.52 × 0.38 × 0.23 |
Data collection | |
Diffractometer | Bruker Kappa APEXII CCD |
Absorption correction | Multi-scan (SADABS; Bruker, 2014) |
Tmin, Tmax | 0.80, 0.90 |
No. of measured, independent and observed [I > 3σ(I)] reflections | 9529, 1538, 1407 |
Rint | 0.031 |
(sin θ/λ)max (Å−1) | 0.808 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.024, 0.038, 2.24 |
No. of reflections | 1538 |
No. of parameters | 64 |
H-atom treatment | All H-atom parameters refined |
Δρmax, Δρmin (e Å−3) | 0.49, −0.18 |
Computer programs: APEX2 (Bruker, 2014), SAINT (Bruker, 2014), SUPERFLIP (Palatinus & Chapuis, 2007), JANA2006 (Petříček et al., 2014), XP in SHELXTL (Sheldrick, 2008) and Mercury (Macrae et al., 2006), publCIF (Westrip, 2010).
Acknowledgements
The X-ray centre of TU Wien is acknowledged for providing access to the single-crystal diffractometer.
References
Aguiar, S. R. M. M. de, Öztopcu, Ö., Stöger, B., Mereiter, K., Veiros, L. F., Pittenauer, E., Allmaier, G. & Kirchner, K. (2014). Dalton Trans. 43, 14669–14679. PubMed Google Scholar
Benito-Garagorri, D., Kirchner, K. & Mereiter, K. (2007). Private communication (refcode IFOQAW). CCDC, Cambridge, England. Google Scholar
Bruker (2014). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Gelmboldt, V. O., Ganin, E. V., Fonari, M. S., Koroeva, L. V., Ivanov, Y. E. & Botoshansky, M. M. (2009). J. Fluor. Chem. 130, 428–433. CSD CrossRef 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
Haddad, S. F. & Al-Far, R. H. (2003). Acta Cryst. E59, o1444–o1446. Web of Science CSD CrossRef IUCr Journals Google Scholar
Jazdoń, M., Radecka-Paryzek, W. & Kubicki, M. (2007). Acta Cryst. E63, o3337. Web of Science CSD CrossRef IUCr Journals Google Scholar
Kristiansson, O. (2000). Z. Kristallogr. New Cryst. Struct. 215, 138. Google Scholar
Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453–457. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Mastalir, M., de Aguiar, S. R. M. M., Glatz, M., Stöger, B. & Kirchner, K. (2016). Organometallics, 35, 229–232. CrossRef CAS Google Scholar
Öztopcu, Ö., Holzhacker, C., Puchberger, M., Weil, M., Mereiter, K., Veiros, L. F. & Kirchner, K. (2013). Organometallics, 32, 3042–3052. PubMed Google Scholar
Palatinus, L. & Chapuis, G. (2007). J. Appl. Cryst. 40, 786–790. Web of Science CrossRef CAS IUCr Journals Google Scholar
Petříček, V., Dušek, M. & Palatinus, L. (2014). Z. Kristallogr. 229, 345–352. Google Scholar
Said, S. & Naili, H. (2014). Private communication (refcode KORRAM). CCDC, Cambridge, England. Google Scholar
Schwalbe, C. H., Williams, G. J. B. & Koetzle, T. F. (1987). Acta Cryst. C43, 2191–2195. CSD CrossRef CAS Web of Science IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Szabo, K. J. & Wendt, O. F. (2014). In Pincer and Pincer-Type Complexes: Applications in Organic Synthesis and Catalysis. Weinheim: Wiley-VCH. Google Scholar
Turrell, P. J., Wright, J. A. & Pickett, C. J. (2010). Private communication (refcode GOLMIF). CCDC, Cambridge, England. Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar
Yu, G. (2012). Acta Cryst. E68, o2751. CSD 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.