Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229616005143/cu3094sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229616005143/cu3094Iasup2.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229616005143/cu3094Ibsup3.hkl |
CCDC references: 1470704; 1470703
\ The capacity of pincer complexes as catalysts in organic transformations such as the Suzuki–Miyaura couplings and their potential application in materials, medicine and biology has been well studied (Morales-Morales, 2008; Serrano-Becerra & Morales-Morales, 2009; van Koten et al., 2013). Pincer complexes exhibit robust structures and high thermal stability attributed to the tridentate coordination of the pincer ligands and the strong σ M—C bond (Morales-Morales, 2008; Selander & Szabo, 2011). In recent years, nickel derivatives of these ligands have become of wide interest due to their high catalytic activities in cross-coupling reactions and other potentially industrial relevant transformations, which were once exclusive to palladium or other group 10 transition metal complexes (Han, 2013).
Thus, nickel pincer complexes including PCP, POCOP and POCN pincer ligands, among others, have been synthesized (Salah & Zargarian, 2011). As expected, the phosphinite POCOP pincer complexes produced showed good thermal stability and presented several advantages in comparison with other pincer complexes, mainly their facile synthesis and the ease of tuning of both their sterics and electronics, turning them into valuable species for potential applications in different areas of chemistry.
Previously, Morales-Morales and co-workers reported the facile and high-yield synthesis of the title compound, [2,6-bis(di-tert-butylphosphinoyl)-4-(3,5-dinitrobenzoyloxy)phenyl-\ κ3P,C1,P']chloridonickel(II), represented as [NiCl{C6H2-4-[OCOC6H4-3,5-(NO2)2]-2,6-(OPtBu2)2}] (I), and the crystal structures of some analogous NiII pincer derivatives, i.e. [NiCl{C6H2-4-(OCOC6H5)-2,6-(OPtBu2)2}] and [NiCl{C6H2-4-(OCOC6H4-4-OCH3)-2,6-(OPtBu2)2}] (García-Eleno, et al. 2015). We report here the crystal structures of two polymorphs ofn the pincer nickel(II) complex (I).
The synthesis of the title compound was performed as reported previously (García-Eleno, et al. 2015). A Schlenk flask with a rubber septum was charged with one equivalent of the tBuPOCOtBuP ligand dissolved in dry toluene (20 ml) and one equivalent of NiCl2·6H2O. The resulting reaction mixture was refluxed for 12 h. After this time, the resulting mixture was allowed to cool to room temperature and was then filtered and the solvent evaporated under vacuum. The solid residue was passed through a short column of silica gel and eluted with CH2Cl2. Further elimination of the solvent under vacuum provides the title pincer complex as microcrystalline green powder. The compound was obtained in 73% yield (m.p. 532 K). Elemental analyses (experimental/calculated): C 49.64/49.71, H 5.89/5.96, N 3.99/3.94%. 1H NMR (CDCl3, 298 K, 300.52 MHz): δ 1.44 (m, 36H), 6.34 (s, 2H), 9.22 (m, 1H), 9.24 (d, 1H). 13C{1H} NMR (CDCl3, 298 K, 75.57 MHz): δ 27.78, 39.33, 98.79, 123.39, 130.37, 134.07, 149.51, 151.09, 161.03, 169.89. 31P{1H} NMR (CDCl3, 298 K, 121.65 Hz): δ 189.91. EM (FAB+; m/z): 700 [M]+ (100%), 665 [M - Cl]+ (50%). IR (KBr; nmax/cm-1): 1752, 1546, 1263.
Crystal data, data collection and structure refinement details are summarized in Table 1. All H atoms were placed in idealized positions and refined in riding mode, such that Uiso(H) = 1.2Ueq(parent atom). C—H distances of 0.93 and 0.96 Å were used for methine and methyl H atoms, respectively. In polymorph (Ia), the methyl groups (C15, C16 and C17) are disordered over two sites with an occupancy ratio of 0.50 (3):0.50 (3).
The crystal structure of polymorphs (Ia) and (Ib) of the title complex are shown in Fig. 1, and the principal bond lengths and angles are summarized in Tables 2 and 3. The asymmetric units of the polymorphs are formed by one molecule of the pincer complex having the NiII ion tetracoorinated in a distorted square-planar geometry; this distortion is demonstrated by the values of the angles around the NiII atom being different from 90° in both complexes (see Tables 2 and 3). Polymorph (Ia) crystallizes in an orthorhombic (Pbca) space group, while polymorph (Ib) crystallizes in a monoclinic (Cc) space group.
The coordination around the NiII atom in both polymorphs consists of one chloride ligand and one phosphinite POCOP ligand, namely 2,6-bis(di-tert-butylphosphinoyl)-4-(3,5-dinitrobenzyloxy)phenyl, coordinated in a tridentate manner through one C and two P atoms, forming two five-membered rings (i.e. Ni—P—O—C—C), with C—Ni—P bite angles of 82.03 (11) and 81.92 (11)° for (Ia), and 82.49 (16) and 81.65 (16)° for (Ib). The values of the bond lengths and angles around the NiII atom are similar to those observed in other NiII POCOP pincer complexes reported previously (García-Eleno et al. 2015; Salah et al. 2015).
The conformational differences between the two polymorphs are reflected in the dihedral angles formed by the six-membered arene rings. Thus, in polymorph (Ia), the rings are nearly coplanar, with the angle between the mean planes being 27.9 (1)°, while in polymorph (Ib), the corresponding dihedral angle is 82.64 (1)°, which shows that the rings are almost perpendicular. For comparison purposes, in pincer complex [NiCl{C6H2-4-(OCOC6H5)-2,6-(OPtBu2)2}], the arene rings are perpendicular, with a dihedral angle of 89.9 (5)°.
An examination of the molecular packing in both polymorphs reveals the molecules to be connected mainly by two types of C—H···O interactions, where the O atoms of the carbonyl (O═C) and nitro (NO2) groups act as acceptors of hydrogen bonds (Tables 4 and 5). Although the interactions are weak (Desiraju, 2005), they are responsible for the supramolecular arrangement.
In polymorph (Ia), C6—H6···O6i and C11—H11···O4ii hydrogen bonds give rise to 11-membered macrocycles (Fig. 2 and Table 4), which extend parallel to the [100] direction, forming a linear arrangement. Furthermore, these linear chains are connected by C24—H24C···O8iii interactions, generating a layer arrangement parallel to the ab plane (Fig. 3 and Table 4). The crystal network is completed by the presence of a C13—H13···O5iv interaction that extends the arrangement along the [010] direction (Table 4).
In polymorph (Ib), a similar 11-membered macrocycle to that in (Ia) is observed, although in this case the ring is twisted (Fig. 4). The ring is formed by C6—H6···O8vi and C11—H11···O4v interactions having torsion angles for C6—H6—O8—N2 and C11—H11—O4—C7 of -86.63 (1) and -136.94 (1)°, respectively. In contrast, these angles in polymorph (Ia) have values of 109.55 (1) and -118.48 (1)°, respectively. The 11-membered rings extend parallel to the [001] direction. In the same direction, an eight-membered ring is formed by C15—H15A···O7vii and C17—H17A···O8vii hydrogen bonds (Fig. 4 and Table 5); this arrangement is completed by the presence of C23—H23C···O6vi and one lp–π (lp = lone pair) interactions (Fig. 5). The lp–π interaction is formed by the nitro O6 atom with the centroid (Cg) of the C1–C6 arene ring of the pincer ligand, with an O..Cg distance of 3.420 (6) Å [symmetry code: (v) x, -y+1, z+1/2]. The O···C distances are between 3.446 (6) and 3.901 (6) Å, and are larger than the sum of van der Waals radii of O and C (3.22 Å; Bondi, 1964) indicative of a weak lp–π interaction (Mooibroek et al. 2008).
Although the complexes have aromatic rings, aromatic interactions, such as π–π and C—H···π interactions, are not determinant as a consequence of the presence of bulky and electron-withdrawing groups. The supramolecular arrangement is formed by the weak C—H···O═X (X = C, N) interactions.
\ The capacity of pincer complexes as catalysts in organic transformations such as the Suzuki–Miyaura couplings and their potential application in materials, medicine and biology has been well studied (Morales-Morales, 2008; Serrano-Becerra & Morales-Morales, 2009; van Koten et al., 2013). Pincer complexes exhibit robust structures and high thermal stability attributed to the tridentate coordination of the pincer ligands and the strong σ M—C bond (Morales-Morales, 2008; Selander & Szabo, 2011). In recent years, nickel derivatives of these ligands have become of wide interest due to their high catalytic activities in cross-coupling reactions and other potentially industrial relevant transformations, which were once exclusive to palladium or other group 10 transition metal complexes (Han, 2013).
Thus, nickel pincer complexes including PCP, POCOP and POCN pincer ligands, among others, have been synthesized (Salah & Zargarian, 2011). As expected, the phosphinite POCOP pincer complexes produced showed good thermal stability and presented several advantages in comparison with other pincer complexes, mainly their facile synthesis and the ease of tuning of both their sterics and electronics, turning them into valuable species for potential applications in different areas of chemistry.
Previously, Morales-Morales and co-workers reported the facile and high-yield synthesis of the title compound, [2,6-bis(di-tert-butylphosphinoyl)-4-(3,5-dinitrobenzoyloxy)phenyl-\ κ3P,C1,P']chloridonickel(II), represented as [NiCl{C6H2-4-[OCOC6H4-3,5-(NO2)2]-2,6-(OPtBu2)2}] (I), and the crystal structures of some analogous NiII pincer derivatives, i.e. [NiCl{C6H2-4-(OCOC6H5)-2,6-(OPtBu2)2}] and [NiCl{C6H2-4-(OCOC6H4-4-OCH3)-2,6-(OPtBu2)2}] (García-Eleno, et al. 2015). We report here the crystal structures of two polymorphs ofn the pincer nickel(II) complex (I).
The crystal structure of polymorphs (Ia) and (Ib) of the title complex are shown in Fig. 1, and the principal bond lengths and angles are summarized in Tables 2 and 3. The asymmetric units of the polymorphs are formed by one molecule of the pincer complex having the NiII ion tetracoorinated in a distorted square-planar geometry; this distortion is demonstrated by the values of the angles around the NiII atom being different from 90° in both complexes (see Tables 2 and 3). Polymorph (Ia) crystallizes in an orthorhombic (Pbca) space group, while polymorph (Ib) crystallizes in a monoclinic (Cc) space group.
The coordination around the NiII atom in both polymorphs consists of one chloride ligand and one phosphinite POCOP ligand, namely 2,6-bis(di-tert-butylphosphinoyl)-4-(3,5-dinitrobenzyloxy)phenyl, coordinated in a tridentate manner through one C and two P atoms, forming two five-membered rings (i.e. Ni—P—O—C—C), with C—Ni—P bite angles of 82.03 (11) and 81.92 (11)° for (Ia), and 82.49 (16) and 81.65 (16)° for (Ib). The values of the bond lengths and angles around the NiII atom are similar to those observed in other NiII POCOP pincer complexes reported previously (García-Eleno et al. 2015; Salah et al. 2015).
The conformational differences between the two polymorphs are reflected in the dihedral angles formed by the six-membered arene rings. Thus, in polymorph (Ia), the rings are nearly coplanar, with the angle between the mean planes being 27.9 (1)°, while in polymorph (Ib), the corresponding dihedral angle is 82.64 (1)°, which shows that the rings are almost perpendicular. For comparison purposes, in pincer complex [NiCl{C6H2-4-(OCOC6H5)-2,6-(OPtBu2)2}], the arene rings are perpendicular, with a dihedral angle of 89.9 (5)°.
An examination of the molecular packing in both polymorphs reveals the molecules to be connected mainly by two types of C—H···O interactions, where the O atoms of the carbonyl (O═C) and nitro (NO2) groups act as acceptors of hydrogen bonds (Tables 4 and 5). Although the interactions are weak (Desiraju, 2005), they are responsible for the supramolecular arrangement.
In polymorph (Ia), C6—H6···O6i and C11—H11···O4ii hydrogen bonds give rise to 11-membered macrocycles (Fig. 2 and Table 4), which extend parallel to the [100] direction, forming a linear arrangement. Furthermore, these linear chains are connected by C24—H24C···O8iii interactions, generating a layer arrangement parallel to the ab plane (Fig. 3 and Table 4). The crystal network is completed by the presence of a C13—H13···O5iv interaction that extends the arrangement along the [010] direction (Table 4).
In polymorph (Ib), a similar 11-membered macrocycle to that in (Ia) is observed, although in this case the ring is twisted (Fig. 4). The ring is formed by C6—H6···O8vi and C11—H11···O4v interactions having torsion angles for C6—H6—O8—N2 and C11—H11—O4—C7 of -86.63 (1) and -136.94 (1)°, respectively. In contrast, these angles in polymorph (Ia) have values of 109.55 (1) and -118.48 (1)°, respectively. The 11-membered rings extend parallel to the [001] direction. In the same direction, an eight-membered ring is formed by C15—H15A···O7vii and C17—H17A···O8vii hydrogen bonds (Fig. 4 and Table 5); this arrangement is completed by the presence of C23—H23C···O6vi and one lp–π (lp = lone pair) interactions (Fig. 5). The lp–π interaction is formed by the nitro O6 atom with the centroid (Cg) of the C1–C6 arene ring of the pincer ligand, with an O..Cg distance of 3.420 (6) Å [symmetry code: (v) x, -y+1, z+1/2]. The O···C distances are between 3.446 (6) and 3.901 (6) Å, and are larger than the sum of van der Waals radii of O and C (3.22 Å; Bondi, 1964) indicative of a weak lp–π interaction (Mooibroek et al. 2008).
Although the complexes have aromatic rings, aromatic interactions, such as π–π and C—H···π interactions, are not determinant as a consequence of the presence of bulky and electron-withdrawing groups. The supramolecular arrangement is formed by the weak C—H···O═X (X = C, N) interactions.
The synthesis of the title compound was performed as reported previously (García-Eleno, et al. 2015). A Schlenk flask with a rubber septum was charged with one equivalent of the tBuPOCOtBuP ligand dissolved in dry toluene (20 ml) and one equivalent of NiCl2·6H2O. The resulting reaction mixture was refluxed for 12 h. After this time, the resulting mixture was allowed to cool to room temperature and was then filtered and the solvent evaporated under vacuum. The solid residue was passed through a short column of silica gel and eluted with CH2Cl2. Further elimination of the solvent under vacuum provides the title pincer complex as microcrystalline green powder. The compound was obtained in 73% yield (m.p. 532 K). Elemental analyses (experimental/calculated): C 49.64/49.71, H 5.89/5.96, N 3.99/3.94%. 1H NMR (CDCl3, 298 K, 300.52 MHz): δ 1.44 (m, 36H), 6.34 (s, 2H), 9.22 (m, 1H), 9.24 (d, 1H). 13C{1H} NMR (CDCl3, 298 K, 75.57 MHz): δ 27.78, 39.33, 98.79, 123.39, 130.37, 134.07, 149.51, 151.09, 161.03, 169.89. 31P{1H} NMR (CDCl3, 298 K, 121.65 Hz): δ 189.91. EM (FAB+; m/z): 700 [M]+ (100%), 665 [M - Cl]+ (50%). IR (KBr; nmax/cm-1): 1752, 1546, 1263.
Crystal data, data collection and structure refinement details are summarized in Table 1. All H atoms were placed in idealized positions and refined in riding mode, such that Uiso(H) = 1.2Ueq(parent atom). C—H distances of 0.93 and 0.96 Å were used for methine and methyl H atoms, respectively. In polymorph (Ia), the methyl groups (C15, C16 and C17) are disordered over two sites with an occupancy ratio of 0.50 (3):0.50 (3).
For both compounds, data collection: APEX2 (Bruker, 2012); cell refinement: APEX2 (Bruker, 2012); data reduction: SAINT (Bruker, 2012); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b); molecular graphics: DIAMOND (Brandenburg, 2006); software used to prepare material for publication: PLATON (Spek, 2009) and DIAMOND (Brandenburg, 2006).
[Ni(C29H41N2O8P2)Cl] | Dx = 1.393 Mg m−3 |
Mr = 701.74 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, Pbca | Cell parameters from 9798 reflections |
a = 11.7012 (7) Å | θ = 2.2–23.8° |
b = 16.2076 (10) Å | µ = 0.80 mm−1 |
c = 35.285 (2) Å | T = 298 K |
V = 6691.8 (7) Å3 | Prism, yellow |
Z = 8 | 0.42 × 0.14 × 0.04 mm |
F(000) = 2944 |
Bruker SMART APEX CCD area-detector diffractometer | 4488 reflections with I > 2σ(I) |
Detector resolution: 0.83 pixels mm-1 | Rint = 0.118 |
ω scans | θmax = 25.4°, θmin = 2.1° |
Absorption correction: multi-scan (SADABS; Bruker, 2014) | h = −14→14 |
Tmin = 0.615, Tmax = 0.745 | k = −19→19 |
70240 measured reflections | l = −42→42 |
6137 independent reflections |
Refinement on F2 | 96 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.057 | H-atom parameters constrained |
wR(F2) = 0.116 | w = 1/[σ2(Fo2) + (0.036P)2 + 6.834P] where P = (Fo2 + 2Fc2)/3 |
S = 1.09 | (Δ/σ)max = 0.001 |
6137 reflections | Δρmax = 0.43 e Å−3 |
425 parameters | Δρmin = −0.25 e Å−3 |
[Ni(C29H41N2O8P2)Cl] | V = 6691.8 (7) Å3 |
Mr = 701.74 | Z = 8 |
Orthorhombic, Pbca | Mo Kα radiation |
a = 11.7012 (7) Å | µ = 0.80 mm−1 |
b = 16.2076 (10) Å | T = 298 K |
c = 35.285 (2) Å | 0.42 × 0.14 × 0.04 mm |
Bruker SMART APEX CCD area-detector diffractometer | 6137 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2014) | 4488 reflections with I > 2σ(I) |
Tmin = 0.615, Tmax = 0.745 | Rint = 0.118 |
70240 measured reflections |
R[F2 > 2σ(F2)] = 0.057 | 96 restraints |
wR(F2) = 0.116 | H-atom parameters constrained |
S = 1.09 | Δρmax = 0.43 e Å−3 |
6137 reflections | Δρmin = −0.25 e Å−3 |
425 parameters |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
Ni1 | 0.01873 (4) | 0.19434 (3) | 0.66190 (2) | 0.03413 (14) | |
Cl1 | −0.01130 (11) | 0.26726 (8) | 0.71337 (3) | 0.0757 (4) | |
P1 | −0.10883 (9) | 0.09795 (7) | 0.67181 (3) | 0.0402 (3) | |
P2 | 0.15571 (8) | 0.26938 (6) | 0.63806 (3) | 0.0308 (2) | |
O1 | −0.0991 (2) | 0.03546 (17) | 0.63486 (7) | 0.0534 (8) | |
O2 | 0.1867 (2) | 0.22687 (15) | 0.59677 (7) | 0.0407 (7) | |
O3 | 0.1366 (2) | −0.01363 (14) | 0.52428 (7) | 0.0430 (7) | |
O4 | 0.0176 (3) | −0.12256 (19) | 0.52699 (10) | 0.0752 (11) | |
O5 | 0.1557 (4) | −0.3847 (2) | 0.47691 (12) | 0.0925 (13) | |
O6 | 0.2796 (3) | −0.3810 (2) | 0.43146 (13) | 0.0995 (14) | |
O7 | 0.5485 (3) | −0.1536 (3) | 0.43505 (14) | 0.1194 (17) | |
O8 | 0.4965 (3) | −0.0382 (2) | 0.45801 (14) | 0.1071 (15) | |
N1 | 0.2267 (4) | −0.3504 (2) | 0.45749 (13) | 0.0655 (12) | |
N2 | 0.4802 (4) | −0.1100 (3) | 0.45087 (11) | 0.0674 (11) | |
C1 | −0.0142 (3) | 0.0599 (2) | 0.60955 (10) | 0.0380 (9) | |
C2 | 0.0437 (3) | 0.1328 (2) | 0.61769 (10) | 0.0314 (8) | |
C3 | 0.1263 (3) | 0.1544 (2) | 0.59077 (10) | 0.0330 (8) | |
C4 | 0.1537 (3) | 0.1063 (2) | 0.55983 (10) | 0.0376 (9) | |
H4 | 0.2109 | 0.1219 | 0.5430 | 0.045* | |
C5 | 0.0933 (3) | 0.0345 (2) | 0.55482 (10) | 0.0343 (9) | |
C6 | 0.0062 (3) | 0.0099 (2) | 0.57877 (10) | 0.0419 (10) | |
H6 | −0.0361 | −0.0377 | 0.5743 | 0.050* | |
C7 | 0.1035 (4) | −0.0907 (3) | 0.51671 (11) | 0.0463 (10) | |
C8 | 0.1911 (3) | −0.1345 (2) | 0.49328 (10) | 0.0388 (9) | |
C9 | 0.1702 (4) | −0.2170 (2) | 0.48520 (11) | 0.0440 (10) | |
H9 | 0.1022 | −0.2416 | 0.4928 | 0.053* | |
C10 | 0.2508 (4) | −0.2623 (2) | 0.46583 (11) | 0.0457 (10) | |
C11 | 0.3521 (4) | −0.2289 (3) | 0.45452 (11) | 0.0496 (11) | |
H11 | 0.4064 | −0.2603 | 0.4417 | 0.060* | |
C12 | 0.3713 (4) | −0.1465 (2) | 0.46284 (11) | 0.0452 (10) | |
C13 | 0.2934 (3) | −0.0993 (2) | 0.48199 (11) | 0.0431 (10) | |
H13 | 0.3090 | −0.0442 | 0.4873 | 0.052* | |
C14 | −0.2607 (3) | 0.1313 (3) | 0.66807 (11) | 0.0591 (11) | |
C15 | −0.305 (2) | 0.1663 (13) | 0.7056 (4) | 0.061 (4) | 0.49 (3) |
H15A | −0.2523 | 0.2067 | 0.7150 | 0.073* | 0.49 (3) |
H15B | −0.3783 | 0.1917 | 0.7016 | 0.073* | 0.49 (3) |
H15C | −0.3127 | 0.1225 | 0.7237 | 0.073* | 0.49 (3) |
C16 | −0.3445 (17) | 0.0665 (12) | 0.6527 (7) | 0.100 (5) | 0.49 (3) |
H16A | −0.3160 | 0.0449 | 0.6292 | 0.121* | 0.49 (3) |
H16B | −0.3521 | 0.0225 | 0.6707 | 0.121* | 0.49 (3) |
H16C | −0.4177 | 0.0917 | 0.6485 | 0.121* | 0.49 (3) |
C17 | −0.2548 (16) | 0.2033 (12) | 0.6391 (5) | 0.074 (4) | 0.49 (3) |
H17A | −0.2271 | 0.1829 | 0.6153 | 0.089* | 0.49 (3) |
H17B | −0.3297 | 0.2263 | 0.6357 | 0.089* | 0.49 (3) |
H17C | −0.2040 | 0.2451 | 0.6484 | 0.089* | 0.49 (3) |
C15A | −0.294 (2) | 0.1907 (11) | 0.6997 (4) | 0.061 (3) | 0.51 (3) |
H15D | −0.2875 | 0.1631 | 0.7237 | 0.073* | 0.51 (3) |
H15E | −0.2433 | 0.2374 | 0.6993 | 0.073* | 0.51 (3) |
H15F | −0.3709 | 0.2089 | 0.6960 | 0.073* | 0.51 (3) |
C16A | −0.3380 (16) | 0.0547 (8) | 0.6690 (7) | 0.084 (4) | 0.51 (3) |
H16D | −0.3164 | 0.0178 | 0.6489 | 0.101* | 0.51 (3) |
H16E | −0.3297 | 0.0272 | 0.6929 | 0.101* | 0.51 (3) |
H16F | −0.4161 | 0.0712 | 0.6656 | 0.101* | 0.51 (3) |
C17A | −0.2697 (18) | 0.1738 (15) | 0.6296 (4) | 0.088 (4) | 0.51 (3) |
H17D | −0.2487 | 0.1357 | 0.6100 | 0.106* | 0.51 (3) |
H17E | −0.3469 | 0.1920 | 0.6257 | 0.106* | 0.51 (3) |
H17F | −0.2193 | 0.2205 | 0.6290 | 0.106* | 0.51 (3) |
C18 | −0.0791 (4) | 0.0241 (3) | 0.71069 (12) | 0.0551 (12) | |
C19 | 0.0495 (5) | 0.0073 (3) | 0.70861 (17) | 0.0903 (18) | |
H19A | 0.0905 | 0.0579 | 0.7124 | 0.108* | |
H19B | 0.0681 | −0.0149 | 0.6842 | 0.108* | |
H19C | 0.0704 | −0.0316 | 0.7279 | 0.108* | |
C20 | −0.1039 (5) | 0.0630 (3) | 0.74929 (13) | 0.0813 (16) | |
H20A | −0.1850 | 0.0683 | 0.7526 | 0.098* | |
H20B | −0.0691 | 0.1166 | 0.7505 | 0.098* | |
H20C | −0.0732 | 0.0286 | 0.7690 | 0.098* | |
C21 | −0.0074 (4) | 0.3663 (3) | 0.60859 (17) | 0.0831 (17) | |
H21A | −0.0349 | 0.4190 | 0.6002 | 0.100* | |
H21B | −0.0545 | 0.3467 | 0.6290 | 0.100* | |
H21C | −0.0103 | 0.3277 | 0.5879 | 0.100* | |
C22 | 0.1157 (3) | 0.3748 (2) | 0.62233 (12) | 0.0437 (10) | |
C23 | 0.1188 (5) | 0.4358 (3) | 0.65525 (15) | 0.0813 (17) | |
H23A | 0.1967 | 0.4457 | 0.6625 | 0.098* | |
H23B | 0.0776 | 0.4133 | 0.6764 | 0.098* | |
H23C | 0.0841 | 0.4868 | 0.6476 | 0.098* | |
C24 | 0.1891 (5) | 0.4071 (3) | 0.59021 (15) | 0.0797 (16) | |
H24A | 0.1889 | 0.3680 | 0.5697 | 0.096* | |
H24B | 0.2660 | 0.4149 | 0.5991 | 0.096* | |
H24C | 0.1590 | 0.4588 | 0.5815 | 0.096* | |
C25 | −0.1418 (6) | −0.0588 (3) | 0.70707 (17) | 0.108 (2) | |
H25A | −0.1153 | −0.0958 | 0.7264 | 0.129* | |
H25B | −0.1268 | −0.0822 | 0.6826 | 0.129* | |
H25C | −0.2225 | −0.0501 | 0.7100 | 0.129* | |
C26 | 0.2971 (3) | 0.2628 (2) | 0.66108 (12) | 0.0444 (10) | |
C27 | 0.3923 (3) | 0.3044 (3) | 0.63900 (13) | 0.0614 (12) | |
H27A | 0.3815 | 0.3631 | 0.6395 | 0.074* | |
H27B | 0.3911 | 0.2855 | 0.6132 | 0.074* | |
H27C | 0.4646 | 0.2909 | 0.6503 | 0.074* | |
C28 | 0.2909 (4) | 0.2966 (3) | 0.70150 (12) | 0.0762 (15) | |
H28A | 0.3616 | 0.2856 | 0.7143 | 0.091* | |
H28B | 0.2294 | 0.2703 | 0.7148 | 0.091* | |
H28C | 0.2779 | 0.3550 | 0.7007 | 0.091* | |
C29 | 0.3234 (4) | 0.1695 (3) | 0.66280 (16) | 0.0775 (16) | |
H29A | 0.3258 | 0.1475 | 0.6376 | 0.093* | |
H29B | 0.2647 | 0.1420 | 0.6770 | 0.093* | |
H29C | 0.3959 | 0.1611 | 0.6749 | 0.093* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Ni1 | 0.0350 (3) | 0.0382 (3) | 0.0292 (2) | −0.0048 (2) | 0.0066 (2) | −0.0084 (2) |
Cl1 | 0.0852 (9) | 0.0859 (9) | 0.0559 (7) | −0.0311 (7) | 0.0324 (6) | −0.0395 (7) |
P1 | 0.0382 (6) | 0.0493 (6) | 0.0330 (5) | −0.0095 (5) | 0.0104 (4) | −0.0103 (5) |
P2 | 0.0344 (5) | 0.0279 (5) | 0.0300 (5) | −0.0005 (4) | 0.0027 (4) | −0.0031 (4) |
O1 | 0.0542 (18) | 0.0638 (19) | 0.0422 (16) | −0.0267 (15) | 0.0213 (14) | −0.0244 (14) |
O2 | 0.0516 (16) | 0.0341 (14) | 0.0365 (15) | −0.0142 (12) | 0.0174 (12) | −0.0086 (12) |
O3 | 0.0604 (18) | 0.0295 (14) | 0.0390 (15) | −0.0061 (13) | 0.0182 (13) | −0.0107 (12) |
O4 | 0.070 (2) | 0.059 (2) | 0.097 (3) | −0.0251 (18) | 0.037 (2) | −0.0392 (19) |
O5 | 0.140 (4) | 0.044 (2) | 0.094 (3) | −0.018 (2) | −0.010 (3) | −0.008 (2) |
O6 | 0.082 (3) | 0.078 (3) | 0.138 (4) | 0.028 (2) | −0.019 (2) | −0.069 (3) |
O7 | 0.084 (3) | 0.118 (3) | 0.156 (4) | 0.000 (3) | 0.062 (3) | −0.054 (3) |
O8 | 0.098 (3) | 0.059 (2) | 0.164 (4) | −0.004 (2) | 0.063 (3) | 0.006 (3) |
N1 | 0.076 (3) | 0.044 (3) | 0.077 (3) | 0.014 (2) | −0.030 (2) | −0.021 (2) |
N2 | 0.067 (3) | 0.071 (3) | 0.064 (3) | 0.009 (2) | 0.021 (2) | −0.002 (2) |
C1 | 0.038 (2) | 0.042 (2) | 0.035 (2) | −0.0063 (18) | 0.0116 (17) | −0.0072 (17) |
C2 | 0.031 (2) | 0.034 (2) | 0.0290 (19) | −0.0013 (16) | 0.0038 (15) | −0.0071 (16) |
C3 | 0.039 (2) | 0.0275 (19) | 0.032 (2) | −0.0014 (17) | 0.0033 (16) | −0.0045 (16) |
C4 | 0.043 (2) | 0.036 (2) | 0.034 (2) | −0.0029 (18) | 0.0121 (17) | −0.0014 (17) |
C5 | 0.044 (2) | 0.031 (2) | 0.0271 (19) | 0.0013 (17) | 0.0057 (17) | −0.0084 (16) |
C6 | 0.045 (2) | 0.043 (2) | 0.038 (2) | −0.0115 (19) | 0.0073 (18) | −0.0134 (18) |
C7 | 0.055 (3) | 0.043 (2) | 0.041 (2) | −0.003 (2) | 0.007 (2) | −0.008 (2) |
C8 | 0.056 (3) | 0.031 (2) | 0.029 (2) | 0.0016 (19) | 0.0024 (18) | −0.0070 (17) |
C9 | 0.059 (3) | 0.034 (2) | 0.039 (2) | −0.0002 (19) | −0.0001 (19) | −0.0074 (18) |
C10 | 0.064 (3) | 0.030 (2) | 0.043 (2) | 0.009 (2) | −0.012 (2) | −0.0099 (19) |
C11 | 0.061 (3) | 0.046 (3) | 0.041 (2) | 0.019 (2) | −0.005 (2) | −0.010 (2) |
C12 | 0.055 (3) | 0.044 (3) | 0.037 (2) | 0.008 (2) | 0.0081 (19) | −0.0019 (19) |
C13 | 0.060 (3) | 0.032 (2) | 0.037 (2) | 0.000 (2) | 0.0054 (19) | −0.0031 (18) |
C14 | 0.035 (2) | 0.090 (3) | 0.052 (2) | −0.006 (2) | 0.0055 (19) | −0.010 (2) |
C15 | 0.052 (7) | 0.072 (8) | 0.058 (5) | 0.006 (8) | 0.016 (5) | 0.003 (5) |
C16 | 0.054 (7) | 0.151 (8) | 0.096 (10) | −0.033 (6) | −0.004 (8) | −0.037 (8) |
C17 | 0.045 (7) | 0.134 (8) | 0.044 (6) | 0.010 (7) | −0.016 (6) | 0.011 (6) |
C15A | 0.059 (7) | 0.064 (7) | 0.059 (6) | 0.008 (7) | 0.015 (5) | 0.003 (5) |
C16A | 0.042 (6) | 0.114 (6) | 0.096 (10) | −0.020 (5) | −0.004 (7) | −0.034 (6) |
C17A | 0.061 (7) | 0.152 (10) | 0.052 (5) | 0.003 (8) | −0.026 (6) | 0.002 (6) |
C18 | 0.065 (3) | 0.050 (3) | 0.050 (3) | −0.008 (2) | 0.010 (2) | 0.000 (2) |
C19 | 0.084 (4) | 0.085 (4) | 0.102 (5) | 0.031 (3) | 0.011 (3) | 0.027 (3) |
C20 | 0.109 (4) | 0.094 (4) | 0.041 (3) | 0.017 (3) | 0.007 (3) | 0.006 (3) |
C21 | 0.066 (3) | 0.060 (3) | 0.123 (5) | 0.008 (3) | −0.030 (3) | 0.023 (3) |
C22 | 0.046 (2) | 0.031 (2) | 0.055 (3) | 0.0061 (18) | −0.004 (2) | 0.0025 (19) |
C23 | 0.102 (4) | 0.040 (3) | 0.102 (4) | 0.014 (3) | 0.005 (3) | −0.019 (3) |
C24 | 0.091 (4) | 0.060 (3) | 0.088 (4) | 0.009 (3) | 0.016 (3) | 0.037 (3) |
C25 | 0.163 (6) | 0.073 (4) | 0.087 (4) | −0.046 (4) | 0.006 (4) | 0.018 (3) |
C26 | 0.038 (2) | 0.044 (2) | 0.052 (3) | −0.0007 (18) | −0.0064 (19) | 0.005 (2) |
C27 | 0.040 (2) | 0.070 (3) | 0.074 (3) | −0.005 (2) | −0.005 (2) | 0.001 (3) |
C28 | 0.063 (3) | 0.116 (4) | 0.049 (3) | −0.016 (3) | −0.019 (2) | 0.003 (3) |
C29 | 0.063 (3) | 0.059 (3) | 0.110 (4) | 0.009 (2) | −0.024 (3) | 0.029 (3) |
Ni1—C2 | 1.875 (3) | C16—H16C | 0.9600 |
Ni1—P2 | 2.1808 (10) | C17—H17A | 0.9600 |
Ni1—P1 | 2.1888 (11) | C17—H17B | 0.9600 |
Ni1—Cl1 | 2.1953 (11) | C17—H17C | 0.9600 |
P1—O1 | 1.655 (3) | C15A—H15D | 0.9600 |
P1—C18 | 1.854 (4) | C15A—H15E | 0.9600 |
P1—C14 | 1.862 (4) | C15A—H15F | 0.9600 |
P2—O2 | 1.652 (2) | C16A—H16D | 0.9600 |
P2—C26 | 1.846 (4) | C16A—H16E | 0.9600 |
P2—C22 | 1.856 (4) | C16A—H16F | 0.9600 |
O1—C1 | 1.393 (4) | C17A—H17D | 0.9600 |
O2—C3 | 1.387 (4) | C17A—H17E | 0.9600 |
O3—C7 | 1.334 (4) | C17A—H17F | 0.9600 |
O3—C5 | 1.424 (4) | C18—C20 | 1.529 (6) |
O4—C7 | 1.187 (5) | C18—C19 | 1.531 (7) |
O5—N1 | 1.212 (5) | C18—C25 | 1.535 (6) |
O6—N1 | 1.214 (5) | C19—H19A | 0.9600 |
O7—N2 | 1.203 (5) | C19—H19B | 0.9600 |
O8—N2 | 1.206 (5) | C19—H19C | 0.9600 |
N1—C10 | 1.485 (5) | C20—H20A | 0.9600 |
N2—C12 | 1.468 (5) | C20—H20B | 0.9600 |
C1—C6 | 1.376 (5) | C20—H20C | 0.9600 |
C1—C2 | 1.391 (5) | C21—C22 | 1.526 (6) |
C2—C3 | 1.399 (5) | C21—H21A | 0.9600 |
C3—C4 | 1.380 (5) | C21—H21B | 0.9600 |
C4—C5 | 1.372 (5) | C21—H21C | 0.9600 |
C4—H4 | 0.9300 | C22—C24 | 1.516 (6) |
C5—C6 | 1.383 (5) | C22—C23 | 1.526 (6) |
C6—H6 | 0.9300 | C23—H23A | 0.9600 |
C7—C8 | 1.496 (5) | C23—H23B | 0.9600 |
C8—C13 | 1.385 (5) | C23—H23C | 0.9600 |
C8—C9 | 1.389 (5) | C24—H24A | 0.9600 |
C9—C10 | 1.376 (5) | C24—H24B | 0.9600 |
C9—H9 | 0.9300 | C24—H24C | 0.9600 |
C10—C11 | 1.363 (6) | C25—H25A | 0.9600 |
C11—C12 | 1.386 (5) | C25—H25B | 0.9600 |
C11—H11 | 0.9300 | C25—H25C | 0.9600 |
C12—C13 | 1.369 (5) | C26—C27 | 1.518 (6) |
C13—H13 | 0.9300 | C26—C28 | 1.529 (6) |
C14—C15A | 1.523 (7) | C26—C29 | 1.544 (6) |
C14—C17A | 1.524 (7) | C27—H27A | 0.9600 |
C14—C15 | 1.531 (7) | C27—H27B | 0.9600 |
C14—C16 | 1.536 (7) | C27—H27C | 0.9600 |
C14—C16A | 1.537 (7) | C28—H28A | 0.9600 |
C14—C17 | 1.552 (7) | C28—H28B | 0.9600 |
C15—H15A | 0.9600 | C28—H28C | 0.9600 |
C15—H15B | 0.9600 | C29—H29A | 0.9600 |
C15—H15C | 0.9600 | C29—H29B | 0.9600 |
C16—H16A | 0.9600 | C29—H29C | 0.9600 |
C16—H16B | 0.9600 | ||
C2—Ni1—P2 | 82.03 (11) | C14—C17—H17C | 109.5 |
C2—Ni1—P1 | 81.92 (11) | H17A—C17—H17C | 109.5 |
P2—Ni1—P1 | 163.92 (4) | H17B—C17—H17C | 109.5 |
C2—Ni1—Cl1 | 179.51 (12) | C14—C15A—H15D | 109.5 |
P2—Ni1—Cl1 | 97.85 (4) | C14—C15A—H15E | 109.5 |
P1—Ni1—Cl1 | 98.21 (4) | H15D—C15A—H15E | 109.5 |
O1—P1—C18 | 100.08 (18) | C14—C15A—H15F | 109.5 |
O1—P1—C14 | 100.84 (16) | H15D—C15A—H15F | 109.5 |
C18—P1—C14 | 114.8 (2) | H15E—C15A—H15F | 109.5 |
O1—P1—Ni1 | 105.30 (10) | C14—C16A—H16D | 109.5 |
C18—P1—Ni1 | 116.83 (15) | C14—C16A—H16E | 109.5 |
C14—P1—Ni1 | 115.59 (14) | H16D—C16A—H16E | 109.5 |
O2—P2—C26 | 99.63 (17) | C14—C16A—H16F | 109.5 |
O2—P2—C22 | 100.11 (16) | H16D—C16A—H16F | 109.5 |
C26—P2—C22 | 114.26 (18) | H16E—C16A—H16F | 109.5 |
O2—P2—Ni1 | 105.60 (9) | C14—C17A—H17D | 109.5 |
C26—P2—Ni1 | 117.17 (13) | C14—C17A—H17E | 109.5 |
C22—P2—Ni1 | 116.30 (13) | H17D—C17A—H17E | 109.5 |
C1—O1—P1 | 112.3 (2) | C14—C17A—H17F | 109.5 |
C3—O2—P2 | 112.1 (2) | H17D—C17A—H17F | 109.5 |
C7—O3—C5 | 124.2 (3) | H17E—C17A—H17F | 109.5 |
O5—N1—O6 | 126.1 (4) | C20—C18—C19 | 107.6 (4) |
O5—N1—C10 | 117.4 (4) | C20—C18—C25 | 110.2 (4) |
O6—N1—C10 | 116.5 (5) | C19—C18—C25 | 108.1 (5) |
O7—N2—O8 | 124.0 (5) | C20—C18—P1 | 111.0 (3) |
O7—N2—C12 | 118.3 (4) | C19—C18—P1 | 105.3 (3) |
O8—N2—C12 | 117.7 (4) | C25—C18—P1 | 114.4 (4) |
C6—C1—C2 | 125.3 (3) | C18—C19—H19A | 109.5 |
C6—C1—O1 | 117.5 (3) | C18—C19—H19B | 109.5 |
C2—C1—O1 | 117.2 (3) | H19A—C19—H19B | 109.5 |
C1—C2—C3 | 114.2 (3) | C18—C19—H19C | 109.5 |
C1—C2—Ni1 | 123.2 (3) | H19A—C19—H19C | 109.5 |
C3—C2—Ni1 | 122.6 (3) | H19B—C19—H19C | 109.5 |
C4—C3—O2 | 118.7 (3) | C18—C20—H20A | 109.5 |
C4—C3—C2 | 123.7 (3) | C18—C20—H20B | 109.5 |
O2—C3—C2 | 117.5 (3) | H20A—C20—H20B | 109.5 |
C5—C4—C3 | 117.5 (3) | C18—C20—H20C | 109.5 |
C5—C4—H4 | 121.2 | H20A—C20—H20C | 109.5 |
C3—C4—H4 | 121.2 | H20B—C20—H20C | 109.5 |
C4—C5—C6 | 123.0 (3) | C22—C21—H21A | 109.5 |
C4—C5—O3 | 112.3 (3) | C22—C21—H21B | 109.5 |
C6—C5—O3 | 124.5 (3) | H21A—C21—H21B | 109.5 |
C1—C6—C5 | 116.1 (3) | C22—C21—H21C | 109.5 |
C1—C6—H6 | 121.9 | H21A—C21—H21C | 109.5 |
C5—C6—H6 | 121.9 | H21B—C21—H21C | 109.5 |
O4—C7—O3 | 126.3 (4) | C24—C22—C21 | 109.2 (4) |
O4—C7—C8 | 122.8 (4) | C24—C22—C23 | 109.4 (4) |
O3—C7—C8 | 110.9 (3) | C21—C22—C23 | 108.8 (4) |
C13—C8—C9 | 119.4 (4) | C24—C22—P2 | 113.5 (3) |
C13—C8—C7 | 123.7 (3) | C21—C22—P2 | 104.5 (3) |
C9—C8—C7 | 116.8 (4) | C23—C22—P2 | 111.3 (3) |
C10—C9—C8 | 119.6 (4) | C22—C23—H23A | 109.5 |
C10—C9—H9 | 120.2 | C22—C23—H23B | 109.5 |
C8—C9—H9 | 120.2 | H23A—C23—H23B | 109.5 |
C11—C10—C9 | 122.0 (4) | C22—C23—H23C | 109.5 |
C11—C10—N1 | 119.3 (4) | H23A—C23—H23C | 109.5 |
C9—C10—N1 | 118.7 (4) | H23B—C23—H23C | 109.5 |
C10—C11—C12 | 117.4 (4) | C22—C24—H24A | 109.5 |
C10—C11—H11 | 121.3 | C22—C24—H24B | 109.5 |
C12—C11—H11 | 121.3 | H24A—C24—H24B | 109.5 |
C13—C12—C11 | 122.4 (4) | C22—C24—H24C | 109.5 |
C13—C12—N2 | 119.7 (4) | H24A—C24—H24C | 109.5 |
C11—C12—N2 | 117.9 (4) | H24B—C24—H24C | 109.5 |
C12—C13—C8 | 119.1 (4) | C18—C25—H25A | 109.5 |
C12—C13—H13 | 120.5 | C18—C25—H25B | 109.5 |
C8—C13—H13 | 120.5 | H25A—C25—H25B | 109.5 |
C15A—C14—C17A | 110.5 (6) | C18—C25—H25C | 109.5 |
C15—C14—C16 | 110.0 (6) | H25A—C25—H25C | 109.5 |
C15A—C14—C16A | 110.3 (6) | H25B—C25—H25C | 109.5 |
C17A—C14—C16A | 110.0 (5) | C27—C26—C28 | 110.8 (4) |
C15—C14—C17 | 107.8 (6) | C27—C26—C29 | 108.0 (4) |
C16—C14—C17 | 108.0 (6) | C28—C26—C29 | 108.9 (4) |
C15A—C14—P1 | 111.9 (10) | C27—C26—P2 | 114.0 (3) |
C17A—C14—P1 | 105.1 (8) | C28—C26—P2 | 110.3 (3) |
C15—C14—P1 | 111.7 (10) | C29—C26—P2 | 104.6 (3) |
C16—C14—P1 | 115.8 (10) | C26—C27—H27A | 109.5 |
C16A—C14—P1 | 109.0 (8) | C26—C27—H27B | 109.5 |
C17—C14—P1 | 102.9 (7) | H27A—C27—H27B | 109.5 |
C14—C15—H15A | 109.5 | C26—C27—H27C | 109.5 |
C14—C15—H15B | 109.5 | H27A—C27—H27C | 109.5 |
H15A—C15—H15B | 109.5 | H27B—C27—H27C | 109.5 |
C14—C15—H15C | 109.5 | C26—C28—H28A | 109.5 |
H15A—C15—H15C | 109.5 | C26—C28—H28B | 109.5 |
H15B—C15—H15C | 109.5 | H28A—C28—H28B | 109.5 |
C14—C16—H16A | 109.5 | C26—C28—H28C | 109.5 |
C14—C16—H16B | 109.5 | H28A—C28—H28C | 109.5 |
H16A—C16—H16B | 109.5 | H28B—C28—H28C | 109.5 |
C14—C16—H16C | 109.5 | C26—C29—H29A | 109.5 |
H16A—C16—H16C | 109.5 | C26—C29—H29B | 109.5 |
H16B—C16—H16C | 109.5 | H29A—C29—H29B | 109.5 |
C14—C17—H17A | 109.5 | C26—C29—H29C | 109.5 |
C14—C17—H17B | 109.5 | H29A—C29—H29C | 109.5 |
H17A—C17—H17B | 109.5 | H29B—C29—H29C | 109.5 |
C18—P1—O1—C1 | −120.2 (3) | O7—N2—C12—C11 | −1.3 (6) |
C14—P1—O1—C1 | 121.9 (3) | O8—N2—C12—C11 | 179.7 (5) |
Ni1—P1—O1—C1 | 1.4 (3) | C11—C12—C13—C8 | −0.5 (6) |
C26—P2—O2—C3 | 116.8 (3) | N2—C12—C13—C8 | −179.7 (4) |
C22—P2—O2—C3 | −126.2 (3) | C9—C8—C13—C12 | 0.5 (6) |
Ni1—P2—O2—C3 | −5.0 (2) | C7—C8—C13—C12 | 175.5 (4) |
P1—O1—C1—C6 | 176.4 (3) | O1—P1—C14—C15A | 179.7 (9) |
P1—O1—C1—C2 | −3.1 (4) | C18—P1—C14—C15A | 73.2 (9) |
C6—C1—C2—C3 | 1.7 (6) | Ni1—P1—C14—C15A | −67.3 (9) |
O1—C1—C2—C3 | −178.9 (3) | O1—P1—C14—C17A | −60.4 (10) |
C6—C1—C2—Ni1 | −175.6 (3) | C18—P1—C14—C17A | −166.9 (10) |
O1—C1—C2—Ni1 | 3.8 (5) | Ni1—P1—C14—C17A | 52.6 (10) |
P2—Ni1—C2—C1 | 177.0 (3) | O1—P1—C14—C15 | 160.8 (9) |
P1—Ni1—C2—C1 | −2.2 (3) | C18—P1—C14—C15 | 54.3 (10) |
P2—Ni1—C2—C3 | −0.1 (3) | Ni1—P1—C14—C15 | −86.3 (10) |
P1—Ni1—C2—C3 | −179.3 (3) | O1—P1—C14—C16 | 33.8 (11) |
P2—O2—C3—C4 | −171.7 (3) | C18—P1—C14—C16 | −72.8 (11) |
P2—O2—C3—C2 | 5.5 (4) | Ni1—P1—C14—C16 | 146.7 (11) |
C1—C2—C3—C4 | −3.6 (5) | O1—P1—C14—C16A | 57.5 (10) |
Ni1—C2—C3—C4 | 173.8 (3) | C18—P1—C14—C16A | −49.0 (10) |
C1—C2—C3—O2 | 179.3 (3) | Ni1—P1—C14—C16A | 170.4 (10) |
Ni1—C2—C3—O2 | −3.3 (5) | O1—P1—C14—C17 | −83.8 (10) |
O2—C3—C4—C5 | 179.3 (3) | C18—P1—C14—C17 | 169.7 (10) |
C2—C3—C4—C5 | 2.2 (6) | Ni1—P1—C14—C17 | 29.1 (10) |
C3—C4—C5—C6 | 1.2 (6) | O1—P1—C18—C20 | −169.8 (3) |
C3—C4—C5—O3 | −174.2 (3) | C14—P1—C18—C20 | −62.8 (4) |
C7—O3—C5—C4 | 170.6 (4) | Ni1—P1—C18—C20 | 77.2 (4) |
C7—O3—C5—C6 | −4.8 (6) | O1—P1—C18—C19 | 74.1 (3) |
C2—C1—C6—C5 | 1.3 (6) | C14—P1—C18—C19 | −178.9 (3) |
O1—C1—C6—C5 | −178.1 (3) | Ni1—P1—C18—C19 | −38.9 (4) |
C4—C5—C6—C1 | −2.9 (6) | O1—P1—C18—C25 | −44.4 (4) |
O3—C5—C6—C1 | 172.0 (3) | C14—P1—C18—C25 | 62.6 (4) |
C5—O3—C7—O4 | 20.2 (7) | Ni1—P1—C18—C25 | −157.4 (3) |
C5—O3—C7—C8 | −159.1 (3) | O2—P2—C22—C24 | −38.2 (4) |
O4—C7—C8—C13 | −178.0 (4) | C26—P2—C22—C24 | 67.3 (4) |
O3—C7—C8—C13 | 1.3 (5) | Ni1—P2—C22—C24 | −151.3 (3) |
O4—C7—C8—C9 | −2.9 (6) | O2—P2—C22—C21 | 80.7 (3) |
O3—C7—C8—C9 | 176.4 (3) | C26—P2—C22—C21 | −173.9 (3) |
C13—C8—C9—C10 | −0.6 (6) | Ni1—P2—C22—C21 | −32.5 (4) |
C7—C8—C9—C10 | −175.9 (4) | O2—P2—C22—C23 | −162.0 (3) |
C8—C9—C10—C11 | 0.8 (6) | C26—P2—C22—C23 | −56.6 (4) |
C8—C9—C10—N1 | 180.0 (4) | Ni1—P2—C22—C23 | 84.8 (3) |
O5—N1—C10—C11 | 158.1 (4) | O2—P2—C26—C27 | 56.5 (3) |
O6—N1—C10—C11 | −22.5 (6) | C22—P2—C26—C27 | −49.2 (4) |
O5—N1—C10—C9 | −21.1 (6) | Ni1—P2—C26—C27 | 169.7 (3) |
O6—N1—C10—C9 | 158.2 (4) | O2—P2—C26—C28 | −178.1 (3) |
C9—C10—C11—C12 | −0.8 (6) | C22—P2—C26—C28 | 76.1 (3) |
N1—C10—C11—C12 | 180.0 (4) | Ni1—P2—C26—C28 | −64.9 (3) |
C10—C11—C12—C13 | 0.7 (6) | O2—P2—C26—C29 | −61.2 (3) |
C10—C11—C12—N2 | 179.9 (4) | C22—P2—C26—C29 | −167.0 (3) |
O7—N2—C12—C13 | 177.9 (5) | Ni1—P2—C26—C29 | 52.0 (3) |
O8—N2—C12—C13 | −1.1 (7) |
D—H···A | D—H | H···A | D···A | D—H···A |
C6—H6···O6i | 0.93 | 2.54 | 3.395 (6) | 154 |
C11—H11···O4ii | 0.93 | 2.55 | 3.158 (6) | 123 |
C24—H24C···O8iii | 0.96 | 2.69 | 3.535 (5) | 147 |
C13—H13···O5iv | 0.93 | 2.64 | 3.533 (4) | 160 |
Symmetry codes: (i) x−1/2, −y−1/2, −z+1; (ii) x+1/2, −y−1/2, −z+1; (iii) x−1/2, −y+1/2, −z+1; (iv) −x+1/2, y+1/2, z. |
[Ni(C29H41N2O8P2)Cl] | F(000) = 1472 |
Mr = 701.74 | Dx = 1.343 Mg m−3 |
Monoclinic, Cc | Mo Kα radiation, λ = 0.71073 Å |
a = 10.9248 (9) Å | Cell parameters from 6354 reflections |
b = 21.5339 (18) Å | θ = 2.3–25.0° |
c = 15.0710 (12) Å | µ = 0.78 mm−1 |
β = 101.851 (1)° | T = 298 K |
V = 3469.9 (5) Å3 | Prism, yellow |
Z = 4 | 0.40 × 0.13 × 0.10 mm |
Bruker SMART APEX CCD area-detector diffractometer | 5343 reflections with I > 2σ(I) |
Detector resolution: 0.83 pixels mm-1 | Rint = 0.035 |
ω scans | θmax = 25.4°, θmin = 1.9° |
Absorption correction: analytical (SADABS; Bruker, 2014) | h = −13→13 |
Tmin = 0.808, Tmax = 0.944 | k = −25→25 |
14268 measured reflections | l = −18→17 |
6265 independent reflections |
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.042 | w = 1/[σ2(Fo2) + (0.0332P)2] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.090 | (Δ/σ)max < 0.001 |
S = 0.98 | Δρmax = 0.47 e Å−3 |
6265 reflections | Δρmin = −0.18 e Å−3 |
400 parameters | Absolute structure: Flack x determined using 2129 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013) |
2 restraints | Absolute structure parameter: 0.054 (9) |
[Ni(C29H41N2O8P2)Cl] | V = 3469.9 (5) Å3 |
Mr = 701.74 | Z = 4 |
Monoclinic, Cc | Mo Kα radiation |
a = 10.9248 (9) Å | µ = 0.78 mm−1 |
b = 21.5339 (18) Å | T = 298 K |
c = 15.0710 (12) Å | 0.40 × 0.13 × 0.10 mm |
β = 101.851 (1)° |
Bruker SMART APEX CCD area-detector diffractometer | 6265 independent reflections |
Absorption correction: analytical (SADABS; Bruker, 2014) | 5343 reflections with I > 2σ(I) |
Tmin = 0.808, Tmax = 0.944 | Rint = 0.035 |
14268 measured reflections |
R[F2 > 2σ(F2)] = 0.042 | H-atom parameters constrained |
wR(F2) = 0.090 | Δρmax = 0.47 e Å−3 |
S = 0.98 | Δρmin = −0.18 e Å−3 |
6265 reflections | Absolute structure: Flack x determined using 2129 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013) |
400 parameters | Absolute structure parameter: 0.054 (9) |
2 restraints |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
x | y | z | Uiso*/Ueq | ||
Ni1 | 0.64515 (5) | 0.23414 (3) | 0.42848 (4) | 0.04456 (18) | |
Cl1 | 0.72001 (17) | 0.17933 (8) | 0.32868 (12) | 0.0765 (5) | |
P1 | 0.76616 (13) | 0.31504 (6) | 0.43229 (10) | 0.0508 (4) | |
P2 | 0.50454 (13) | 0.16828 (7) | 0.45232 (10) | 0.0496 (3) | |
O1 | 0.7249 (4) | 0.36226 (16) | 0.5076 (3) | 0.0590 (10) | |
O2 | 0.4359 (4) | 0.20096 (18) | 0.5281 (3) | 0.0642 (11) | |
O3 | 0.4684 (4) | 0.37610 (18) | 0.7264 (2) | 0.0573 (10) | |
O4 | 0.3108 (4) | 0.43072 (19) | 0.6435 (3) | 0.0651 (11) | |
O5 | 0.1763 (8) | 0.6129 (3) | 0.8029 (4) | 0.159 (4) | |
O6 | 0.2793 (5) | 0.6382 (2) | 0.9322 (4) | 0.0938 (16) | |
O7 | 0.5749 (8) | 0.3977 (3) | 1.0476 (3) | 0.154 (3) | |
O8 | 0.5232 (6) | 0.4772 (2) | 1.1127 (3) | 0.1091 (19) | |
N1 | 0.2558 (6) | 0.6034 (3) | 0.8694 (4) | 0.0753 (16) | |
N2 | 0.5232 (6) | 0.4476 (3) | 1.0459 (3) | 0.0793 (17) | |
C1 | 0.6305 (5) | 0.3378 (2) | 0.5458 (3) | 0.0463 (12) | |
C2 | 0.5823 (5) | 0.2800 (2) | 0.5160 (3) | 0.0433 (12) | |
C3 | 0.4875 (5) | 0.2582 (2) | 0.5568 (4) | 0.0502 (12) | |
C4 | 0.4433 (5) | 0.2892 (3) | 0.6239 (4) | 0.0559 (14) | |
H4 | 0.3797 | 0.2729 | 0.6496 | 0.067* | |
C5 | 0.4975 (5) | 0.3451 (3) | 0.6507 (3) | 0.0501 (13) | |
C6 | 0.5904 (5) | 0.3712 (2) | 0.6132 (3) | 0.0503 (13) | |
H6 | 0.6247 | 0.4096 | 0.6323 | 0.060* | |
C7 | 0.3801 (5) | 0.4200 (2) | 0.7143 (3) | 0.0456 (12) | |
C8 | 0.3813 (5) | 0.4543 (2) | 0.8001 (3) | 0.0435 (12) | |
C9 | 0.3159 (5) | 0.5094 (2) | 0.7962 (3) | 0.0506 (13) | |
H9 | 0.2669 | 0.5229 | 0.7417 | 0.061* | |
C10 | 0.3241 (5) | 0.5441 (2) | 0.8736 (3) | 0.0521 (13) | |
C11 | 0.3912 (5) | 0.5262 (2) | 0.9558 (3) | 0.0505 (13) | |
H11 | 0.3953 | 0.5504 | 1.0075 | 0.061* | |
C12 | 0.4534 (5) | 0.4697 (3) | 0.9582 (3) | 0.0495 (13) | |
C13 | 0.4500 (5) | 0.4340 (3) | 0.8823 (3) | 0.0510 (13) | |
H13 | 0.4935 | 0.3967 | 0.8861 | 0.061* | |
C14 | 0.7327 (7) | 0.3652 (3) | 0.3290 (4) | 0.0655 (16) | |
C15 | 0.7812 (9) | 0.3356 (4) | 0.2507 (5) | 0.102 (3) | |
H15A | 0.7597 | 0.3615 | 0.1979 | 0.123* | |
H15B | 0.7441 | 0.2954 | 0.2377 | 0.123* | |
H15C | 0.8705 | 0.3315 | 0.2673 | 0.123* | |
C16 | 0.7845 (12) | 0.4306 (4) | 0.3457 (8) | 0.147 (4) | |
H16A | 0.8726 | 0.4286 | 0.3708 | 0.176* | |
H16B | 0.7430 | 0.4515 | 0.3875 | 0.176* | |
H16C | 0.7707 | 0.4530 | 0.2895 | 0.176* | |
C17 | 0.5913 (8) | 0.3678 (5) | 0.3044 (6) | 0.114 (3) | |
H17A | 0.5657 | 0.3931 | 0.2514 | 0.137* | |
H17B | 0.5600 | 0.3853 | 0.3539 | 0.137* | |
H17C | 0.5586 | 0.3266 | 0.2923 | 0.137* | |
C18 | 0.9347 (6) | 0.3045 (3) | 0.4830 (5) | 0.0733 (18) | |
C19 | 1.0008 (7) | 0.3654 (4) | 0.5153 (7) | 0.108 (3) | |
H19A | 1.0828 | 0.3567 | 0.5502 | 0.130* | |
H19B | 0.9533 | 0.3875 | 0.5521 | 0.130* | |
H19C | 1.0078 | 0.3904 | 0.4637 | 0.130* | |
C20 | 1.0027 (7) | 0.2708 (3) | 0.4181 (6) | 0.092 (2) | |
H20A | 1.0091 | 0.2978 | 0.3685 | 0.111* | |
H20B | 0.9568 | 0.2342 | 0.3951 | 0.111* | |
H20C | 1.0850 | 0.2593 | 0.4498 | 0.111* | |
C21 | 0.9351 (8) | 0.2625 (5) | 0.5641 (6) | 0.112 (3) | |
H21A | 1.0190 | 0.2584 | 0.5985 | 0.135* | |
H21B | 0.9036 | 0.2223 | 0.5434 | 0.135* | |
H21C | 0.8831 | 0.2802 | 0.6017 | 0.135* | |
C22 | 0.3682 (6) | 0.1556 (3) | 0.3573 (4) | 0.0659 (16) | |
C23 | 0.3278 (8) | 0.2195 (4) | 0.3243 (7) | 0.107 (3) | |
H23A | 0.2545 | 0.2167 | 0.2769 | 0.129* | |
H23B | 0.3938 | 0.2392 | 0.3014 | 0.129* | |
H23C | 0.3093 | 0.2436 | 0.3736 | 0.129* | |
C24 | 0.2616 (7) | 0.1215 (4) | 0.3860 (6) | 0.106 (3) | |
H24A | 0.2406 | 0.1419 | 0.4375 | 0.127* | |
H24B | 0.2865 | 0.0795 | 0.4019 | 0.127* | |
H24C | 0.1901 | 0.1213 | 0.3368 | 0.127* | |
C25 | 0.4079 (7) | 0.1201 (4) | 0.2790 (5) | 0.095 (2) | |
H25A | 0.3407 | 0.1207 | 0.2268 | 0.113* | |
H25B | 0.4273 | 0.0779 | 0.2971 | 0.113* | |
H25C | 0.4803 | 0.1395 | 0.2644 | 0.113* | |
C26 | 0.5649 (6) | 0.0960 (3) | 0.5139 (5) | 0.0713 (17) | |
C27 | 0.4798 (10) | 0.0686 (4) | 0.5704 (7) | 0.118 (3) | |
H27A | 0.4009 | 0.0584 | 0.5321 | 0.141* | |
H27B | 0.4671 | 0.0983 | 0.6152 | 0.141* | |
H27C | 0.5172 | 0.0318 | 0.6000 | 0.141* | |
C28 | 0.5961 (8) | 0.0469 (3) | 0.4492 (7) | 0.099 (2) | |
H28A | 0.6411 | 0.0135 | 0.4834 | 0.119* | |
H28B | 0.6468 | 0.0651 | 0.4110 | 0.119* | |
H28C | 0.5202 | 0.0312 | 0.4124 | 0.119* | |
C29 | 0.6900 (8) | 0.1154 (4) | 0.5746 (6) | 0.116 (3) | |
H29A | 0.7296 | 0.0797 | 0.6064 | 0.139* | |
H29B | 0.6750 | 0.1459 | 0.6176 | 0.139* | |
H29C | 0.7434 | 0.1327 | 0.5378 | 0.139* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Ni1 | 0.0495 (4) | 0.0449 (3) | 0.0432 (3) | 0.0016 (3) | 0.0186 (3) | −0.0056 (3) |
Cl1 | 0.0873 (12) | 0.0704 (10) | 0.0853 (12) | −0.0042 (8) | 0.0496 (10) | −0.0283 (9) |
P1 | 0.0582 (9) | 0.0483 (8) | 0.0521 (8) | −0.0023 (6) | 0.0257 (7) | −0.0051 (7) |
P2 | 0.0529 (8) | 0.0481 (8) | 0.0508 (8) | −0.0022 (6) | 0.0176 (6) | −0.0062 (7) |
O1 | 0.073 (3) | 0.050 (2) | 0.061 (2) | −0.0109 (18) | 0.029 (2) | −0.0148 (19) |
O2 | 0.072 (3) | 0.059 (2) | 0.073 (3) | −0.014 (2) | 0.041 (2) | −0.015 (2) |
O3 | 0.070 (2) | 0.070 (2) | 0.0342 (18) | 0.023 (2) | 0.0164 (17) | −0.0040 (17) |
O4 | 0.078 (3) | 0.075 (3) | 0.041 (2) | 0.019 (2) | 0.011 (2) | −0.005 (2) |
O5 | 0.224 (8) | 0.148 (6) | 0.084 (4) | 0.130 (6) | −0.019 (5) | −0.028 (4) |
O6 | 0.134 (5) | 0.061 (3) | 0.088 (3) | 0.020 (3) | 0.026 (3) | −0.022 (3) |
O7 | 0.227 (8) | 0.162 (6) | 0.055 (3) | 0.119 (6) | −0.011 (4) | −0.005 (4) |
O8 | 0.183 (6) | 0.087 (3) | 0.044 (3) | 0.021 (4) | −0.009 (3) | −0.008 (3) |
N1 | 0.103 (4) | 0.070 (4) | 0.055 (3) | 0.027 (3) | 0.020 (3) | 0.000 (3) |
N2 | 0.111 (5) | 0.085 (4) | 0.038 (3) | 0.025 (4) | 0.007 (3) | 0.003 (3) |
C1 | 0.051 (3) | 0.050 (3) | 0.041 (3) | 0.004 (2) | 0.016 (2) | −0.002 (2) |
C2 | 0.051 (3) | 0.043 (3) | 0.038 (3) | 0.008 (2) | 0.013 (2) | 0.000 (2) |
C3 | 0.055 (3) | 0.051 (3) | 0.047 (3) | 0.000 (3) | 0.018 (2) | −0.001 (3) |
C4 | 0.063 (4) | 0.062 (4) | 0.050 (3) | 0.004 (3) | 0.027 (3) | −0.001 (3) |
C5 | 0.058 (3) | 0.063 (3) | 0.033 (3) | 0.015 (3) | 0.016 (2) | −0.002 (2) |
C6 | 0.061 (3) | 0.047 (3) | 0.042 (3) | 0.007 (3) | 0.009 (2) | −0.007 (2) |
C7 | 0.051 (3) | 0.053 (3) | 0.037 (3) | 0.003 (2) | 0.018 (2) | 0.001 (2) |
C8 | 0.049 (3) | 0.049 (3) | 0.036 (3) | −0.001 (2) | 0.018 (2) | 0.000 (2) |
C9 | 0.057 (3) | 0.061 (3) | 0.036 (3) | 0.010 (3) | 0.014 (2) | 0.004 (3) |
C10 | 0.066 (3) | 0.050 (3) | 0.044 (3) | 0.006 (3) | 0.018 (3) | −0.003 (3) |
C11 | 0.063 (4) | 0.051 (3) | 0.040 (3) | −0.006 (3) | 0.017 (3) | −0.009 (2) |
C12 | 0.053 (3) | 0.061 (3) | 0.035 (3) | −0.001 (3) | 0.010 (2) | −0.001 (2) |
C13 | 0.061 (3) | 0.054 (3) | 0.041 (3) | 0.007 (3) | 0.018 (3) | 0.001 (3) |
C14 | 0.089 (5) | 0.058 (4) | 0.057 (4) | 0.003 (3) | 0.030 (3) | 0.010 (3) |
C15 | 0.138 (8) | 0.121 (7) | 0.062 (5) | 0.017 (6) | 0.055 (5) | 0.012 (5) |
C16 | 0.248 (13) | 0.075 (5) | 0.116 (7) | −0.038 (7) | 0.035 (8) | 0.023 (6) |
C17 | 0.099 (6) | 0.149 (8) | 0.098 (6) | 0.036 (6) | 0.029 (5) | 0.058 (6) |
C18 | 0.057 (4) | 0.084 (5) | 0.082 (5) | −0.009 (3) | 0.021 (3) | −0.012 (4) |
C19 | 0.070 (5) | 0.113 (7) | 0.145 (8) | −0.025 (5) | 0.030 (5) | −0.041 (6) |
C20 | 0.060 (4) | 0.090 (5) | 0.131 (7) | 0.006 (4) | 0.031 (4) | −0.024 (5) |
C21 | 0.072 (5) | 0.159 (9) | 0.099 (6) | 0.003 (5) | 0.000 (5) | 0.023 (6) |
C22 | 0.056 (4) | 0.074 (4) | 0.068 (4) | −0.005 (3) | 0.012 (3) | −0.011 (3) |
C23 | 0.078 (5) | 0.107 (6) | 0.120 (7) | 0.014 (5) | −0.019 (5) | −0.002 (5) |
C24 | 0.074 (5) | 0.132 (7) | 0.112 (7) | −0.034 (5) | 0.019 (4) | −0.022 (6) |
C25 | 0.080 (5) | 0.126 (6) | 0.073 (5) | −0.008 (5) | 0.004 (4) | −0.027 (5) |
C26 | 0.076 (4) | 0.065 (4) | 0.077 (4) | −0.004 (3) | 0.025 (4) | 0.010 (4) |
C27 | 0.160 (9) | 0.087 (5) | 0.131 (7) | 0.012 (6) | 0.087 (7) | 0.035 (6) |
C28 | 0.107 (6) | 0.068 (4) | 0.131 (7) | 0.027 (4) | 0.045 (5) | 0.018 (5) |
C29 | 0.116 (7) | 0.115 (7) | 0.099 (6) | −0.006 (5) | −0.023 (5) | 0.046 (5) |
Ni1—C2 | 1.886 (5) | C15—H15C | 0.9600 |
Ni1—P2 | 2.1741 (15) | C16—H16A | 0.9600 |
Ni1—P1 | 2.1805 (15) | C16—H16B | 0.9600 |
Ni1—Cl1 | 2.1976 (15) | C16—H16C | 0.9600 |
P1—O1 | 1.654 (4) | C17—H17A | 0.9600 |
P1—C18 | 1.857 (7) | C17—H17B | 0.9600 |
P1—C14 | 1.868 (6) | C17—H17C | 0.9600 |
P2—O2 | 1.647 (4) | C18—C21 | 1.521 (11) |
P2—C22 | 1.862 (6) | C18—C19 | 1.529 (10) |
P2—C26 | 1.863 (7) | C18—C20 | 1.527 (9) |
O1—C1 | 1.385 (6) | C19—H19A | 0.9600 |
O2—C3 | 1.386 (6) | C19—H19B | 0.9600 |
O3—C7 | 1.336 (6) | C19—H19C | 0.9600 |
O3—C5 | 1.413 (6) | C20—H20A | 0.9600 |
O4—C7 | 1.198 (6) | C20—H20B | 0.9600 |
O5—N1 | 1.201 (8) | C20—H20C | 0.9600 |
O6—N1 | 1.193 (7) | C21—H21A | 0.9600 |
O7—N2 | 1.210 (7) | C21—H21B | 0.9600 |
O8—N2 | 1.191 (7) | C21—H21C | 0.9600 |
N1—C10 | 1.473 (7) | C22—C23 | 1.498 (10) |
N2—C12 | 1.463 (7) | C22—C24 | 1.514 (9) |
C1—C6 | 1.388 (7) | C22—C25 | 1.542 (9) |
C1—C2 | 1.390 (7) | C23—H23A | 0.9600 |
C2—C3 | 1.390 (7) | C23—H23B | 0.9600 |
C3—C4 | 1.381 (8) | C23—H23C | 0.9600 |
C4—C5 | 1.366 (8) | C24—H24A | 0.9600 |
C4—H4 | 0.9300 | C24—H24B | 0.9600 |
C5—C6 | 1.378 (7) | C24—H24C | 0.9600 |
C6—H6 | 0.9300 | C25—H25A | 0.9600 |
C7—C8 | 1.487 (7) | C25—H25B | 0.9600 |
C8—C13 | 1.380 (7) | C25—H25C | 0.9600 |
C8—C9 | 1.379 (7) | C26—C27 | 1.503 (10) |
C9—C10 | 1.374 (7) | C26—C28 | 1.524 (10) |
C9—H9 | 0.9300 | C26—C29 | 1.538 (10) |
C10—C11 | 1.360 (7) | C27—H27A | 0.9600 |
C11—C12 | 1.390 (8) | C27—H27B | 0.9600 |
C11—H11 | 0.9300 | C27—H27C | 0.9600 |
C12—C13 | 1.373 (7) | C28—H28A | 0.9600 |
C13—H13 | 0.9300 | C28—H28B | 0.9600 |
C14—C17 | 1.513 (10) | C28—H28C | 0.9600 |
C14—C16 | 1.520 (10) | C29—H29A | 0.9600 |
C14—C15 | 1.527 (9) | C29—H29B | 0.9600 |
C15—H15A | 0.9600 | C29—H29C | 0.9600 |
C15—H15B | 0.9600 | ||
C2—Ni1—P2 | 81.65 (16) | C14—C16—H16C | 109.5 |
C2—Ni1—P1 | 82.49 (16) | H16A—C16—H16C | 109.5 |
P2—Ni1—P1 | 164.14 (6) | H16B—C16—H16C | 109.5 |
C2—Ni1—Cl1 | 178.79 (17) | C14—C17—H17A | 109.5 |
P2—Ni1—Cl1 | 97.91 (6) | C14—C17—H17B | 109.5 |
P1—Ni1—Cl1 | 97.95 (6) | H17A—C17—H17B | 109.5 |
O1—P1—C18 | 100.4 (3) | C14—C17—H17C | 109.5 |
O1—P1—C14 | 100.5 (2) | H17A—C17—H17C | 109.5 |
C18—P1—C14 | 114.9 (3) | H17B—C17—H17C | 109.5 |
O1—P1—Ni1 | 105.08 (14) | C21—C18—C19 | 109.4 (7) |
C18—P1—Ni1 | 117.2 (2) | C21—C18—C20 | 108.1 (7) |
C14—P1—Ni1 | 115.2 (2) | C19—C18—C20 | 110.6 (6) |
O2—P2—C22 | 100.9 (3) | C21—C18—P1 | 104.0 (5) |
O2—P2—C26 | 100.2 (3) | C19—C18—P1 | 112.9 (5) |
C22—P2—C26 | 114.0 (3) | C20—C18—P1 | 111.5 (5) |
O2—P2—Ni1 | 105.88 (15) | C18—C19—H19A | 109.5 |
C22—P2—Ni1 | 116.7 (2) | C18—C19—H19B | 109.5 |
C26—P2—Ni1 | 116.0 (2) | H19A—C19—H19B | 109.5 |
C1—O1—P1 | 112.5 (3) | C18—C19—H19C | 109.5 |
C3—O2—P2 | 112.5 (3) | H19A—C19—H19C | 109.5 |
C7—O3—C5 | 120.0 (4) | H19B—C19—H19C | 109.5 |
O6—N1—O5 | 123.8 (6) | C18—C20—H20A | 109.5 |
O6—N1—C10 | 119.0 (6) | C18—C20—H20B | 109.5 |
O5—N1—C10 | 117.2 (6) | H20A—C20—H20B | 109.5 |
O8—N2—O7 | 122.5 (5) | C18—C20—H20C | 109.5 |
O8—N2—C12 | 119.8 (6) | H20A—C20—H20C | 109.5 |
O7—N2—C12 | 117.6 (6) | H20B—C20—H20C | 109.5 |
O1—C1—C6 | 118.8 (5) | C18—C21—H21A | 109.5 |
O1—C1—C2 | 118.2 (4) | C18—C21—H21B | 109.5 |
C6—C1—C2 | 123.0 (5) | H21A—C21—H21B | 109.5 |
C1—C2—C3 | 115.3 (5) | C18—C21—H21C | 109.5 |
C1—C2—Ni1 | 121.8 (4) | H21A—C21—H21C | 109.5 |
C3—C2—Ni1 | 122.9 (4) | H21B—C21—H21C | 109.5 |
C4—C3—O2 | 118.5 (5) | C23—C22—C24 | 110.5 (7) |
C4—C3—C2 | 124.4 (5) | C23—C22—C25 | 108.2 (7) |
O2—C3—C2 | 117.0 (5) | C24—C22—C25 | 109.3 (6) |
C5—C4—C3 | 116.6 (5) | C23—C22—P2 | 104.8 (5) |
C5—C4—H4 | 121.7 | C24—C22—P2 | 113.1 (5) |
C3—C4—H4 | 121.7 | C25—C22—P2 | 110.8 (4) |
C4—C5—C6 | 123.3 (5) | C22—C23—H23A | 109.5 |
C4—C5—O3 | 119.9 (5) | C22—C23—H23B | 109.5 |
C6—C5—O3 | 116.4 (5) | H23A—C23—H23B | 109.5 |
C5—C6—C1 | 117.4 (5) | C22—C23—H23C | 109.5 |
C5—C6—H6 | 121.3 | H23A—C23—H23C | 109.5 |
C1—C6—H6 | 121.3 | H23B—C23—H23C | 109.5 |
O4—C7—O3 | 124.4 (5) | C22—C24—H24A | 109.5 |
O4—C7—C8 | 124.8 (5) | C22—C24—H24B | 109.5 |
O3—C7—C8 | 110.9 (4) | H24A—C24—H24B | 109.5 |
C13—C8—C9 | 119.5 (5) | C22—C24—H24C | 109.5 |
C13—C8—C7 | 121.9 (5) | H24A—C24—H24C | 109.5 |
C9—C8—C7 | 118.6 (4) | H24B—C24—H24C | 109.5 |
C10—C9—C8 | 119.3 (5) | C22—C25—H25A | 109.5 |
C10—C9—H9 | 120.4 | C22—C25—H25B | 109.5 |
C8—C9—H9 | 120.4 | H25A—C25—H25B | 109.5 |
C11—C10—C9 | 123.3 (5) | C22—C25—H25C | 109.5 |
C11—C10—N1 | 117.3 (5) | H25A—C25—H25C | 109.5 |
C9—C10—N1 | 119.4 (5) | H25B—C25—H25C | 109.5 |
C10—C11—C12 | 116.2 (5) | C27—C26—C28 | 109.7 (6) |
C10—C11—H11 | 121.9 | C27—C26—C29 | 110.3 (7) |
C12—C11—H11 | 121.9 | C28—C26—C29 | 106.3 (7) |
C13—C12—C11 | 122.6 (5) | C27—C26—P2 | 114.4 (5) |
C13—C12—N2 | 119.4 (5) | C28—C26—P2 | 111.3 (5) |
C11—C12—N2 | 118.1 (5) | C29—C26—P2 | 104.4 (5) |
C12—C13—C8 | 119.2 (5) | C26—C27—H27A | 109.5 |
C12—C13—H13 | 120.4 | C26—C27—H27B | 109.5 |
C8—C13—H13 | 120.4 | H27A—C27—H27B | 109.5 |
C17—C14—C16 | 109.4 (8) | C26—C27—H27C | 109.5 |
C17—C14—C15 | 109.0 (7) | H27A—C27—H27C | 109.5 |
C16—C14—C15 | 109.7 (7) | H27B—C27—H27C | 109.5 |
C17—C14—P1 | 103.9 (4) | C26—C28—H28A | 109.5 |
C16—C14—P1 | 113.2 (6) | C26—C28—H28B | 109.5 |
C15—C14—P1 | 111.3 (5) | H28A—C28—H28B | 109.5 |
C14—C15—H15A | 109.5 | C26—C28—H28C | 109.5 |
C14—C15—H15B | 109.5 | H28A—C28—H28C | 109.5 |
H15A—C15—H15B | 109.5 | H28B—C28—H28C | 109.5 |
C14—C15—H15C | 109.5 | C26—C29—H29A | 109.5 |
H15A—C15—H15C | 109.5 | C26—C29—H29B | 109.5 |
H15B—C15—H15C | 109.5 | H29A—C29—H29B | 109.5 |
C14—C16—H16A | 109.5 | C26—C29—H29C | 109.5 |
C14—C16—H16B | 109.5 | H29A—C29—H29C | 109.5 |
H16A—C16—H16B | 109.5 | H29B—C29—H29C | 109.5 |
C18—P1—O1—C1 | −121.5 (4) | N1—C10—C11—C12 | 179.2 (5) |
C14—P1—O1—C1 | 120.5 (4) | C10—C11—C12—C13 | 1.1 (8) |
Ni1—P1—O1—C1 | 0.6 (4) | C10—C11—C12—N2 | −177.9 (5) |
C22—P2—O2—C3 | −124.0 (4) | O8—N2—C12—C13 | −177.4 (6) |
C26—P2—O2—C3 | 118.9 (4) | O7—N2—C12—C13 | −0.6 (10) |
Ni1—P2—O2—C3 | −2.0 (4) | O8—N2—C12—C11 | 1.6 (9) |
P1—O1—C1—C6 | 177.1 (4) | O7—N2—C12—C11 | 178.5 (7) |
P1—O1—C1—C2 | −1.4 (6) | C11—C12—C13—C8 | −0.7 (8) |
O1—C1—C2—C3 | −179.8 (4) | N2—C12—C13—C8 | 178.3 (5) |
C6—C1—C2—C3 | 1.8 (8) | C9—C8—C13—C12 | −1.0 (8) |
O1—C1—C2—Ni1 | 1.6 (7) | C7—C8—C13—C12 | 176.1 (5) |
C6—C1—C2—Ni1 | −176.8 (4) | O1—P1—C14—C17 | −71.2 (6) |
P2—Ni1—C2—C1 | 179.2 (4) | C18—P1—C14—C17 | −178.0 (5) |
P1—Ni1—C2—C1 | −0.9 (4) | Ni1—P1—C14—C17 | 41.1 (6) |
P2—Ni1—C2—C3 | 0.7 (4) | O1—P1—C14—C16 | 47.4 (7) |
P1—Ni1—C2—C3 | −179.4 (5) | C18—P1—C14—C16 | −59.3 (7) |
P2—O2—C3—C4 | −176.6 (4) | Ni1—P1—C14—C16 | 159.8 (6) |
P2—O2—C3—C2 | 2.7 (6) | O1—P1—C14—C15 | 171.6 (5) |
C1—C2—C3—C4 | −1.6 (8) | C18—P1—C14—C15 | 64.8 (6) |
Ni1—C2—C3—C4 | 177.0 (4) | Ni1—P1—C14—C15 | −76.1 (6) |
C1—C2—C3—O2 | 179.2 (5) | O1—P1—C18—C21 | 73.3 (6) |
Ni1—C2—C3—O2 | −2.3 (7) | C14—P1—C18—C21 | −179.8 (5) |
O2—C3—C4—C5 | 179.4 (5) | Ni1—P1—C18—C21 | −39.7 (6) |
C2—C3—C4—C5 | 0.2 (8) | O1—P1—C18—C19 | −45.1 (6) |
C3—C4—C5—C6 | 1.1 (8) | C14—P1—C18—C19 | 61.7 (7) |
C3—C4—C5—O3 | −172.3 (5) | Ni1—P1—C18—C19 | −158.2 (5) |
C7—O3—C5—C4 | −95.8 (6) | O1—P1—C18—C20 | −170.4 (5) |
C7—O3—C5—C6 | 90.3 (6) | C14—P1—C18—C20 | −63.5 (6) |
C4—C5—C6—C1 | −0.9 (8) | Ni1—P1—C18—C20 | 76.6 (5) |
O3—C5—C6—C1 | 172.7 (4) | O2—P2—C22—C23 | 68.0 (6) |
O1—C1—C6—C5 | −179.0 (5) | C26—P2—C22—C23 | 174.4 (6) |
C2—C1—C6—C5 | −0.7 (8) | Ni1—P2—C22—C23 | −46.2 (6) |
C5—O3—C7—O4 | 9.5 (8) | O2—P2—C22—C24 | −52.4 (6) |
C5—O3—C7—C8 | −169.4 (4) | C26—P2—C22—C24 | 54.0 (6) |
O4—C7—C8—C13 | 170.1 (6) | Ni1—P2—C22—C24 | −166.5 (5) |
O3—C7—C8—C13 | −11.0 (7) | O2—P2—C22—C25 | −175.5 (5) |
O4—C7—C8—C9 | −12.8 (8) | C26—P2—C22—C25 | −69.1 (6) |
O3—C7—C8—C9 | 166.1 (5) | Ni1—P2—C22—C25 | 70.3 (5) |
C13—C8—C9—C10 | 2.3 (8) | O2—P2—C26—C27 | 36.5 (7) |
C7—C8—C9—C10 | −174.9 (5) | C22—P2—C26—C27 | −70.4 (7) |
C8—C9—C10—C11 | −1.9 (8) | Ni1—P2—C26—C27 | 149.9 (6) |
C8—C9—C10—N1 | 179.1 (5) | O2—P2—C26—C28 | 161.5 (5) |
O6—N1—C10—C11 | 13.5 (9) | C22—P2—C26—C28 | 54.6 (6) |
O5—N1—C10—C11 | −164.4 (7) | Ni1—P2—C26—C28 | −85.1 (5) |
O6—N1—C10—C9 | −167.5 (6) | O2—P2—C26—C29 | −84.2 (6) |
O5—N1—C10—C9 | 14.6 (10) | C22—P2—C26—C29 | 169.0 (5) |
C9—C10—C11—C12 | 0.2 (8) | Ni1—P2—C26—C29 | 29.2 (6) |
D—H···A | D—H | H···A | D···A | D—H···A |
C11—H11···O4i | 0.93 | 2.45 | 3.264 (6) | 146 |
C6—H6···O8ii | 0.93 | 2.67 | 3.346 (6) | 130 |
C23—H23C···O6ii | 0.96 | 2.74 | 3.559 (6) | 144 |
C15—H15A···O7iii | 0.96 | 2.82 | 3.652 (6) | 154 |
C17—H17A···O8iii | 0.96 | 2.73 | 3.683 (4) | 171 |
C24—H24C···O3iv | 0.96 | 2.64 | 3.589 (6) | 169 |
Symmetry codes: (i) x, −y+1, z+1/2; (ii) x, −y+1, z−1/2; (iii) x, y, z−1; (iv) x−1/2, −y+1/2, z−1/2. |
Experimental details
(Ia) | (Ib) | |
Crystal data | ||
Chemical formula | [Ni(C29H41N2O8P2)Cl] | [Ni(C29H41N2O8P2)Cl] |
Mr | 701.74 | 701.74 |
Crystal system, space group | Orthorhombic, Pbca | Monoclinic, Cc |
Temperature (K) | 298 | 298 |
a, b, c (Å) | 11.7012 (7), 16.2076 (10), 35.285 (2) | 10.9248 (9), 21.5339 (18), 15.0710 (12) |
α, β, γ (°) | 90, 90, 90 | 90, 101.851 (1), 90 |
V (Å3) | 6691.8 (7) | 3469.9 (5) |
Z | 8 | 4 |
Radiation type | Mo Kα | Mo Kα |
µ (mm−1) | 0.80 | 0.78 |
Crystal size (mm) | 0.42 × 0.14 × 0.04 | 0.40 × 0.13 × 0.10 |
Data collection | ||
Diffractometer | Bruker SMART APEX CCD area-detector | Bruker SMART APEX CCD area-detector |
Absorption correction | Multi-scan (SADABS; Bruker, 2014) | Analytical (SADABS; Bruker, 2014) |
Tmin, Tmax | 0.615, 0.745 | 0.808, 0.944 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 70240, 6137, 4488 | 14268, 6265, 5343 |
Rint | 0.118 | 0.035 |
(sin θ/λ)max (Å−1) | 0.603 | 0.603 |
Refinement | ||
R[F2 > 2σ(F2)], wR(F2), S | 0.057, 0.116, 1.09 | 0.042, 0.090, 0.98 |
No. of reflections | 6137 | 6265 |
No. of parameters | 425 | 400 |
No. of restraints | 96 | 2 |
H-atom treatment | H-atom parameters constrained | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.43, −0.25 | 0.47, −0.18 |
Absolute structure | ? | Flack x determined using 2129 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013) |
Absolute structure parameter | ? | 0.054 (9) |
Computer programs: APEX2 (Bruker, 2012), SAINT (Bruker, 2012), SHELXT (Sheldrick, 2015a), SHELXL2014 (Sheldrick, 2015b), PLATON (Spek, 2009) and DIAMOND (Brandenburg, 2006).
Ni1—C2 | 1.875 (3) | Ni1—Cl1 | 2.1953 (11) |
Ni1—P2 | 2.1808 (10) | P1—O1 | 1.655 (3) |
Ni1—P1 | 2.1888 (11) | P2—O2 | 1.652 (2) |
C2—Ni1—P2 | 82.03 (11) | C2—Ni1—Cl1 | 179.51 (12) |
C2—Ni1—P1 | 81.92 (11) | P2—Ni1—Cl1 | 97.85 (4) |
P2—Ni1—P1 | 163.92 (4) | P1—Ni1—Cl1 | 98.21 (4) |
Ni1—C2 | 1.886 (5) | Ni1—Cl1 | 2.1976 (15) |
Ni1—P2 | 2.1741 (15) | P1—O1 | 1.654 (4) |
Ni1—P1 | 2.1805 (15) | P2—O2 | 1.647 (4) |
C2—Ni1—P2 | 81.65 (16) | C2—Ni1—Cl1 | 178.79 (17) |
C2—Ni1—P1 | 82.49 (16) | P2—Ni1—Cl1 | 97.91 (6) |
P2—Ni1—P1 | 164.14 (6) | P1—Ni1—Cl1 | 97.95 (6) |
D—H···A | D—H | H···A | D···A | D—H···A |
C6—H6···O6i | 0.93 | 2.54 | 3.395 (6) | 154 |
C11—H11···O4ii | 0.93 | 2.55 | 3.158 (6) | 123 |
C24—H24C···O8iii | 0.96 | 2.69 | 3.535 (5) | 147 |
C13—H13···O5iv | 0.93 | 2.64 | 3.533 (4) | 160 |
Symmetry codes: (i) x−1/2, −y−1/2, −z+1; (ii) x+1/2, −y−1/2, −z+1; (iii) x−1/2, −y+1/2, −z+1; (iv) −x+1/2, y+1/2, z. |
D—H···A | D—H | H···A | D···A | D—H···A |
C11—H11···O4i | 0.93 | 2.45 | 3.264 (6) | 146 |
C6—H6···O8ii | 0.93 | 2.67 | 3.346 (6) | 130 |
C23—H23C···O6ii | 0.96 | 2.74 | 3.559 (6) | 144 |
C15—H15A···O7iii | 0.96 | 2.82 | 3.652 (6) | 154 |
C17—H17A···O8iii | 0.96 | 2.73 | 3.683 (4) | 171 |
C24—H24C···O3iv | 0.96 | 2.64 | 3.589 (6) | 169 |
Symmetry codes: (i) x, −y+1, z+1/2; (ii) x, −y+1, z−1/2; (iii) x, y, z−1; (iv) x−1/2, −y+1/2, z−1/2. |