research communications
catena-poly[[(dimethyl sulfoxide-κO)(pyridine-2,6-dicarboxylato-κ3O,N,O′)nickel(II)]-μ-pyrazine-κ2N:N′]
ofaDepartment of Chemistry and Environmental Science, Grenfell Campus, Memorial University of Newfoundland, Corner Brook, NL, A2H 5G4, Canada, and bDepartment of Chemistry, University of Florida, Gainesville, FL 32611-7200, USA
*Correspondence e-mail: cliu@grenfell.mun.ca
The title coordination polymer, [Ni(C7H3NO4)(C4H4N2)(C2H6OS)]n, consists of [010] chains composed of NiII ions linked by bis-monodentate-bridging pyrazine molecules. Each of the two crystallographically distinct NiII ions is located on a mirror plane and is additionally coordinated by a dimethyl sulfoxide (DMSO) ligand through the oxygen atom and by a tridentate 2,6-pyridine-dicarboxylic acid dianion through one of each of the carboxylate oxygen atoms and the pyridine nitrogen atom, leading to a distorted octahedral coordination environment. The title structure exhibits an interesting complementarity between coordinative bonding and π–π stacking where the Ni—Ni distance of 7.0296 (4) Å across bridging pyrazine ligands allows the pyridine moieties on two adjacent chains to interdigitate at halfway of the Ni—Ni distance, resulting in π–π stacking between pyridine moieties with a centroid-to-plane distance of 3.5148 (2) Å. The double-chain thus formed also exhibits C—H⋯π interactions between pyridine C—H groups on one chain and pyrazine molecules on the other chain. As a result, the interior of the double-chain structure is dominated by π–π stacking and C—H⋯ π interactions, while the space between the double-chains is occupied by a C—H⋯O hydrogen-bonding network involving DMSO ligands and carboxylate groups located on the exterior of the double-chains. This separation of dissimilar interactions in the interior and exterior of the double-chains further stabilizes the crystal structure.
Keywords: crystal structure; one-dimensional NiII coordination polymer; pyridine-2,6-dicarboxylic acid; pyrazine; π–π stacking; C—H⋯ π interaction; hydrogen bonding.
CCDC reference: 1476677
1. Chemical context
In general, π–π interactions are considered important mechanisms for molecular recognition and may function as structure-directing factors in the design and preparation of coordination polymers. However, π–π interactions are not always observed in the final coordination polymer simply by using starting materials containing aromatic moieties. During our investigation of the rational design and synthesis of coordination polymers, we have previously reported a dinuclear NiII complex obtained by reacting 2,6-pyridine dicarboxylic acid and nickel carbonate using water as solvent (Liu et al., 2011). The intermolecular force between the dinuclear complexes is dominated by hydrogen bonding. We recently repeated the synthesis of this compound using dimethyl sulfoxide (DMSO) as solvent under solvothermal conditions and obtained the title compound. We herein report its synthesis and structure which exhibits both π–π stacking and C—H⋯π interactions involving two different aromatic molecules, viz. pyridine and pyrazine.
2. Structural commentary
The II complexes with mirror symmetry (denoted A and B), where each of the NiII atoms is coordinated by a 2,6-pyridine-dicarboxylic acid dianion, a pyrazine molecule, and a DMSO ligand (Fig. 1). The tridentate 2,6-pyridine-dicarboxylate anion coordinates to NiII in a meridional fashion via the pyridine nitrogen atom and two carboxylate oxygen atoms; the DMSO molecule coordinates to NiII through its oxygen atom and the pyrazine ligands through their N atoms. Thus each NiII is in an N3O3 coordination environment. Individual NiII complexes are linked along the axial positions by bis-monodentate bridging pyrazine molecules to form a linear chain parallel to [010] and propagated through mirror symmetry elements passing through the NiII atoms, the anions, and bisecting both the pyrazine ligands and the DMSO molecules along the S=O bonds. In the chains, the Ni—Ni distance across bridging pyrazine is 7.0296 (4) Å, i.e. the length of the b axis.
contains two half Ni3. Supramolecular features
In the crystal, two NiII chains form a double-chain structure via π–π stacking between their pyridine moieties (Fig. 2). Two stacked pyridine rings in the double-chain structure are separated by a centroid-to-plane distance of 3.5148 (2) Å. This separation distance is half of the Ni—Ni distance, indicating that the formation of π–π stacking in the double-chain structure may have been promoted by coordinative bonding distances across bridging pyrazine ligands. A search in the literature returned only a few other examples of coordination polymers exhibiting similar structural features (Zheng et al., 2000; Nawrot et al., 2015). Within the double-chain, two π–π stacked pyridine moieties are also parallel-shifted by 1.50422 (8) Å, consistent with values obtained from computational studies (Huber et al., 2014). Although π–π stacking interactions are prevalent among systems composed of discrete aromatic molecules, it is not always observed in coordination polymers synthesized from aromatic starting materials. The title structure thus provides an interesting example for further investigation on the interplay between coordinative bonding and π–π stacking as a potential strategy for incorporating π–π stacking in the design and synthesis of coordination polymers.
Accompanying the π–π stacking interaction described above, there is also a T-shaped C—H⋯π interaction between the pyridine C4—H4 group and the bridging pyrazine molecule (Tiekink & Zuckerman-Schpector, 2012), contributing additional stability to the double-chain structure. The concurrence of both parallel π–π stacking and T-shaped C—H⋯π interactions in crystal structures is known in the literature, but primarily among systems of discrete aromatic molecules (Tiekink & Zuckerman-Schpector, 2012). We are aware of only one other example of a coordination polymer exhibiting this feature (Felloni et al., 2010). In the C —H⋯π configuration of the title structure, the centroid-to-centroid distance between pyridine and pyrazine is 4.8389 (2) Å, which includes the pyridine C4—H4 bond length of 0.95 Å and a distance of 2.53310 (12) Å from the pyridine H4 atom to the centroid of the pyrazine ring. Although the title structure is a coordination polymer, these distances are in good agreement with results of computational studies performed on discrete aromatic molecules (Mishra & Sathyamurthy, 2005; Hohenstein & Sherrill, 2009; Huber et al., 2014).
In contrast to the π–π stacking and C—H⋯π interactions forming the interior of the double-chains, the exterior of the double-chains is mainly occupied by polar DMSO molecules and carboxylate groups. As a result, a network of C—H⋯O hydrogen bonds exists in the space between the double-chains (Fig. 3), linking double-chains to form a three dimensional network. Double-chains of molecule B are linked by C21B—H21A⋯O2Bii to form sheets parallel to (001). Double-chains of molecule A are linked by C21A—H21E⋯O2Ai/iv, C12A—H12A⋯O1Ai, C21A—H21D⋯O4Aiii, and C22A—H22D⋯O4Aiii hydrogen bonds to form sheets extending along the same direction. Thus, alternating sheets with an ABAB pattern can be observed. Two neighboring sheets are connected via C11A—H11A⋯O5B and C11B—H11B⋯O5A hydrogen bonds to form a three-dimensional network. The hydrogen-bond lengths and angles are summarized in Table 1.
In summary, a separation of dissimilar interactions can be observed between the non-covalent lipophilic π–π stacking and C—H⋯π interactions in the interior of the double-chains and the polar hydrogen bonds in the exterior of the double-chains, further stabilizing the crystal structure.
4. Synthesis and crystallization
Anhydrous NiCO3 (0.67 mmol, 79.15 mg), 2,6-pyridine dicarboxylic acid (0.67 mmol, 111.41 mg), and pyrazine (1.00 mmol, 80.09 mg) were dissolved in 10 ml dimethyl sulfoxide. The resulting mixture was transferred into a stainless steel autoclave which was heated at 373 K for 24 h and cooled to room temperature at a cooling rate of 0.1 K per minute. Green needle-like crystals of the title compound were collected by filtration. Selected IR bands (KBr, cm−1): 1640.6 (C=O), 1367.9 (C—O), 950.9 (S=O), 480.6 (bridging pyrazine).
5. Refinement
Crystal data, data collection and structure . All H atoms were positioned geometrically (C—H = 0.93/1.00 Å) and allowed to ride with Uiso(H)= 1.2/1.5Ueq(C). Methyl H atoms were allowed to rotate around the corresponding C—C bond. There are two disordered parts, both of which are in molecule A. The carboxylate atom O2A sits just outside of the mirror plane (occupancy 0.5) and one of the DMSO methyl groups is disordered over two positions in a ratio of 0.54 (2):0.46 (2). The C atom of this group was refined with isotropic displacement parameters.
details are summarized in Table 2
|
Supporting information
CCDC reference: 1476677
10.1107/S2056989016007064/wm5288sup1.cif
contains datablock I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S2056989016007064/wm5288Isup2.hkl
In general, π–π interactions are considered important mechanisms for molecular recognition and may function as structure-directing factors in the design and preparation of coordination polymers. However, π–π interactions are not always observed in the final coordination polymer simply by using starting materials containing aromatic moieties. During our investigation of the rational design and synthesis of coordination polymers, we have previously reported a dinuclear NiII complex obtained by reacting 2,6-pyridine dicarboxylic acid and nickel carbonate using water as solvent (Liu et al., 2011). The intermolecular force between the dinuclear complexes is dominated by hydrogen bonding. We recently repeated the synthesis of this compound using dimethyl sulfoxide (DMSO) as solvent under solvothermal conditions and obtained the title compound. We herein report its synthesis and structure which exhibits both π–π stacking and C—H···π interactions involving two different aromatic molecules, viz. pyridine and pyrazine.
The ═O bonds. In the chains, the Ni—Ni distance across bridging pyrazine is 7.0296 (4) Å, i.e. the length of the b axis.
contains two half NiII complexes with mirror symmetry (denoted A and B), where each of the NiII atoms is coordinated by a 2,6-pyridine-dicarboxylic acid dianion, a pyrazine molecule, and a DMSO ligand (Fig. 1). The tridentate 2,6-pyridine dicarboxylate anion coordinates to NiII in a meridional fashion via the pyridine nitrogen atom and two carboxylate oxygen atoms; the DMSO molecule coordinates to NiII through its oxygen atom and the pyrazine ligands through their N atoms. Thus each NiII is in an N3O3 coordination environment. Individual NiII complexes are linked along the axial positions by bis-monodentate bridging pyrazine molecules to form a linear chain parallel to [010] and propagated through mirror symmetry elements passing through the NiII atoms, the anions, and bisecting both the pyrazine ligands and the DMSO molecules along the SIn the crystal, two NiII chains form a double-chain structure via π–π stacking between their pyridine moieties (Fig. 2). Two stacked pyridine rings in the double-chain structure are separated by a centroid-to-plane distance of 3.5148 (2) Å. This separation distance is half of the Ni—Ni distance, indicating that the formation of π–π stacking in the double-chain structure may have been promoted by coordinative bonding distances across bridging pyrazine ligands. A search in the literature returned only a few other examples of coordination polymers exhibiting similar structural features (Zheng et al., 2000; Nawrot et al., 2015). Within the double-chain, two π–π stacked pyridine moieties are also parallel-shifted by 1.50422 (8) Å, consistent with values obtained from computational studies (Huber et al., 2014). Although π–π stacking interactions are prevalent among systems composed of discrete aromatic molecules, it is not always observed in coordination polymers synthesized from aromatic starting materials. The title structure thus provides an interesting example for further investigation on the interplay between coordinative bonding and π–π stacking as a potential strategy for incorporating π–π stacking in the design and synthesis of coordination polymers.
Accompanying the π–π stacking interaction described above, there is also a T-shaped C—H···π interaction between the pyridine C4—H4 group and the bridging pyrazine molecule (Tiekink & Zuckerman-Schpector, 2012), contributing additional stability to the double-chain structure. The concurrence of both parallel π–π stacking and T-shaped C—H···π interactions in crystal structures is known in the literature, but primarily among systems of discrete aromatic molecules (Tiekink & Zuckerman-Schpector, 2012). We are aware of only one other example of a coordination polymer exhibiting this feature (Felloni et al., 2010). In the C —H···π configuration of the title structure, the centroid-to-centroid distance between pyridine and pyrazine is 4.8389 (2) Å, which includes the pyridine C4—H4 bond length of 0.95 Å and a distance of 2.53310 (12) Å from the pyridine H4 atom to the centroid of the pyrazine ring. Although the title structure is a coordination polymer, these distances are in good agreement with results of computational studies performed on discrete aromatic molecules (Mishra & Sathyamurthy, 2005; Hohenstein & Sherrill, 2009; Huber et al., 2014).
In contrast to the π–π stacking and C—H···π interactions forming the interior of the double-chains, the exterior of the double-chains is mainly occupied by polar DMSO molecules and carboxylate groups. As a result, a network of C—H···O hydrogen bonds exists in the space between the double-chains (Fig. 3), linking double-chains to form a three dimensional network. Double-chains of molecule B are linked by C21B—H21A···O2Bii to form sheets parallel to (001). Double-chains of molecule A are linked by C21A—H21E···O2Ai/iv, C12A—H12A···O1Ai, C21A—H21D···O4Aiii, and C22A—H22D···O4Aiii hydrogen bonds to form sheets extending along the same direction. Thus, alternating sheets with an ABAB pattern can be observed. Two neighboring sheets are connected via C11A—H11A···O5B and C11B—H11B···O5A hydrogen bonds to form a three-dimensional network. The hydrogen-bond lengths and angles are summarized in Table 1.
In summary, a separation of dissimilar interactions can be observed between the non-covalent lipophilic π–π stacking and C—H···π interactions in the interior of the double-chains and the polar hydrogen bonds in the exterior of the double-chains, further stabilizing the crystal structure.
Anhydrous NiCO3 (0.67 mmol, 79.15 mg), 2,6-pyridine dicarboxylic acid (0.67 mmol, 111.41 mg), and pyrazine (1.00 mmol, 80.09 mg) were dissolved in 10 ml dimethyl sulfoxide. The resulting mixture was transferred into a stainless steel autoclave which was heated at 373 K for 24 h and cooled to room temperature at a cooling rate of 0.1 K per minute. Green needle-like crystals of the title compound were collected by filtration. Selected IR (KBr, cm–1): 1640.55 (C═O), 1367.91 (C—O), 950.92 (S═O), 480.64 (bridging pyrazine).
Crystal data, data collection and structure
details are summarized in Table 2. All H atoms were positioned geometrically ( C—H = 0.93/1.00 Å) and allowed to ride with Uiso(H)= 1.2/1.5Ueq(C). Methyl H atoms were allowed to rotate around the corresponding C—C bond. There are two disordered parts, both of which are in molecule A. The carboxylate atom O2A sits just outside of the mirror plane (occupancy 0.5) and one of the DMSO methyl groups is disordered over two positions in a ratio of 0.54 (2):0.46 (2). The C atom of this group was refined with isotropic displacement parameters.In general, π–π interactions are considered important mechanisms for molecular recognition and may function as structure-directing factors in the design and preparation of coordination polymers. However, π–π interactions are not always observed in the final coordination polymer simply by using starting materials containing aromatic moieties. During our investigation of the rational design and synthesis of coordination polymers, we have previously reported a dinuclear NiII complex obtained by reacting 2,6-pyridine dicarboxylic acid and nickel carbonate using water as solvent (Liu et al., 2011). The intermolecular force between the dinuclear complexes is dominated by hydrogen bonding. We recently repeated the synthesis of this compound using dimethyl sulfoxide (DMSO) as solvent under solvothermal conditions and obtained the title compound. We herein report its synthesis and structure which exhibits both π–π stacking and C—H···π interactions involving two different aromatic molecules, viz. pyridine and pyrazine.
The ═O bonds. In the chains, the Ni—Ni distance across bridging pyrazine is 7.0296 (4) Å, i.e. the length of the b axis.
contains two half NiII complexes with mirror symmetry (denoted A and B), where each of the NiII atoms is coordinated by a 2,6-pyridine-dicarboxylic acid dianion, a pyrazine molecule, and a DMSO ligand (Fig. 1). The tridentate 2,6-pyridine dicarboxylate anion coordinates to NiII in a meridional fashion via the pyridine nitrogen atom and two carboxylate oxygen atoms; the DMSO molecule coordinates to NiII through its oxygen atom and the pyrazine ligands through their N atoms. Thus each NiII is in an N3O3 coordination environment. Individual NiII complexes are linked along the axial positions by bis-monodentate bridging pyrazine molecules to form a linear chain parallel to [010] and propagated through mirror symmetry elements passing through the NiII atoms, the anions, and bisecting both the pyrazine ligands and the DMSO molecules along the SIn the crystal, two NiII chains form a double-chain structure via π–π stacking between their pyridine moieties (Fig. 2). Two stacked pyridine rings in the double-chain structure are separated by a centroid-to-plane distance of 3.5148 (2) Å. This separation distance is half of the Ni—Ni distance, indicating that the formation of π–π stacking in the double-chain structure may have been promoted by coordinative bonding distances across bridging pyrazine ligands. A search in the literature returned only a few other examples of coordination polymers exhibiting similar structural features (Zheng et al., 2000; Nawrot et al., 2015). Within the double-chain, two π–π stacked pyridine moieties are also parallel-shifted by 1.50422 (8) Å, consistent with values obtained from computational studies (Huber et al., 2014). Although π–π stacking interactions are prevalent among systems composed of discrete aromatic molecules, it is not always observed in coordination polymers synthesized from aromatic starting materials. The title structure thus provides an interesting example for further investigation on the interplay between coordinative bonding and π–π stacking as a potential strategy for incorporating π–π stacking in the design and synthesis of coordination polymers.
Accompanying the π–π stacking interaction described above, there is also a T-shaped C—H···π interaction between the pyridine C4—H4 group and the bridging pyrazine molecule (Tiekink & Zuckerman-Schpector, 2012), contributing additional stability to the double-chain structure. The concurrence of both parallel π–π stacking and T-shaped C—H···π interactions in crystal structures is known in the literature, but primarily among systems of discrete aromatic molecules (Tiekink & Zuckerman-Schpector, 2012). We are aware of only one other example of a coordination polymer exhibiting this feature (Felloni et al., 2010). In the C —H···π configuration of the title structure, the centroid-to-centroid distance between pyridine and pyrazine is 4.8389 (2) Å, which includes the pyridine C4—H4 bond length of 0.95 Å and a distance of 2.53310 (12) Å from the pyridine H4 atom to the centroid of the pyrazine ring. Although the title structure is a coordination polymer, these distances are in good agreement with results of computational studies performed on discrete aromatic molecules (Mishra & Sathyamurthy, 2005; Hohenstein & Sherrill, 2009; Huber et al., 2014).
In contrast to the π–π stacking and C—H···π interactions forming the interior of the double-chains, the exterior of the double-chains is mainly occupied by polar DMSO molecules and carboxylate groups. As a result, a network of C—H···O hydrogen bonds exists in the space between the double-chains (Fig. 3), linking double-chains to form a three dimensional network. Double-chains of molecule B are linked by C21B—H21A···O2Bii to form sheets parallel to (001). Double-chains of molecule A are linked by C21A—H21E···O2Ai/iv, C12A—H12A···O1Ai, C21A—H21D···O4Aiii, and C22A—H22D···O4Aiii hydrogen bonds to form sheets extending along the same direction. Thus, alternating sheets with an ABAB pattern can be observed. Two neighboring sheets are connected via C11A—H11A···O5B and C11B—H11B···O5A hydrogen bonds to form a three-dimensional network. The hydrogen-bond lengths and angles are summarized in Table 1.
In summary, a separation of dissimilar interactions can be observed between the non-covalent lipophilic π–π stacking and C—H···π interactions in the interior of the double-chains and the polar hydrogen bonds in the exterior of the double-chains, further stabilizing the crystal structure.
Anhydrous NiCO3 (0.67 mmol, 79.15 mg), 2,6-pyridine dicarboxylic acid (0.67 mmol, 111.41 mg), and pyrazine (1.00 mmol, 80.09 mg) were dissolved in 10 ml dimethyl sulfoxide. The resulting mixture was transferred into a stainless steel autoclave which was heated at 373 K for 24 h and cooled to room temperature at a cooling rate of 0.1 K per minute. Green needle-like crystals of the title compound were collected by filtration. Selected IR (KBr, cm–1): 1640.55 (C═O), 1367.91 (C—O), 950.92 (S═O), 480.64 (bridging pyrazine).
detailsCrystal data, data collection and structure
details are summarized in Table 2. All H atoms were positioned geometrically ( C—H = 0.93/1.00 Å) and allowed to ride with Uiso(H)= 1.2/1.5Ueq(C). Methyl H atoms were allowed to rotate around the corresponding C—C bond. There are two disordered parts, both of which are in molecule A. The carboxylate atom O2A sits just outside of the mirror plane (occupancy 0.5) and one of the DMSO methyl groups is disordered over two positions in a ratio of 0.54 (2):0.46 (2). The C atom of this group was refined with isotropic displacement parameters.Data collection: APEX2 (Bruker, 2014); cell
SAINT (Bruker, 2014); data reduction: SAINT (Bruker, 2014); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b); molecular graphics: XP (Bruker, 2014); software used to prepare material for publication: publCIF (Westrip, 2010).Fig. 1. A view of the asymmetric unit of the title compound, showing the atom labelling. Displacement ellipsoids are drawn at 50% probability level. All disordered components are shown. | |
Fig. 2. A view of the double-chain structure of the title compound running parallel to [010]. | |
Fig. 3. Crystal packing of the title compound, showing hydrogen-bonding interactions as dashed lines. |
[Ni(C7H3NO4)(C4H4N2)(C2H6OS)] | F(000) = 784 |
Mr = 382.03 | Dx = 1.678 Mg m−3 |
Monoclinic, P21/m | Mo Kα radiation, λ = 0.71073 Å |
a = 10.5631 (7) Å | Cell parameters from 9922 reflections |
b = 7.0296 (4) Å | θ = 2.0–28.0° |
c = 20.3710 (13) Å | µ = 1.45 mm−1 |
β = 90.6447 (11)° | T = 100 K |
V = 1512.54 (16) Å3 | Needle, green |
Z = 4 | 0.37 × 0.15 × 0.05 mm |
Bruker APEXII DUO CCD diffractometer | 3549 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.026 |
phi and ω scans | θmax = 27.5°, θmin = 1.0° |
Absorption correction: analytical based on measured indexed crystal faces; XPREP (Bruker, 2014) | h = −13→13 |
Tmin = 0.730, Tmax = 0.965 | k = −9→9 |
56634 measured reflections | l = −26→26 |
3756 independent reflections |
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)] = 0.020 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.055 | H-atom parameters constrained |
S = 1.07 | w = 1/[σ2(Fo2) + (0.0274P)2 + 1.0377P] where P = (Fo2 + 2Fc2)/3 |
3756 reflections | (Δ/σ)max = 0.001 |
256 parameters | Δρmax = 0.43 e Å−3 |
0 restraints | Δρmin = −0.31 e Å−3 |
[Ni(C7H3NO4)(C4H4N2)(C2H6OS)] | V = 1512.54 (16) Å3 |
Mr = 382.03 | Z = 4 |
Monoclinic, P21/m | Mo Kα radiation |
a = 10.5631 (7) Å | µ = 1.45 mm−1 |
b = 7.0296 (4) Å | T = 100 K |
c = 20.3710 (13) Å | 0.37 × 0.15 × 0.05 mm |
β = 90.6447 (11)° |
Bruker APEXII DUO CCD diffractometer | 3756 independent reflections |
Absorption correction: analytical based on measured indexed crystal faces; XPREP (Bruker, 2014) | 3549 reflections with I > 2σ(I) |
Tmin = 0.730, Tmax = 0.965 | Rint = 0.026 |
56634 measured reflections |
R[F2 > 2σ(F2)] = 0.020 | 0 restraints |
wR(F2) = 0.055 | H-atom parameters constrained |
S = 1.07 | Δρmax = 0.43 e Å−3 |
3756 reflections | Δρmin = −0.31 e Å−3 |
256 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) | |
Ni1A | 0.19703 (2) | 0.7500 | 0.11633 (2) | 0.00831 (6) | |
Ni1B | 0.27491 (2) | 0.2500 | 0.36354 (2) | 0.00767 (6) | |
S1B | 0.54518 (4) | 0.2500 | 0.28209 (2) | 0.01208 (9) | |
S1A | −0.08847 (4) | 0.7500 | 0.16036 (2) | 0.01425 (10) | |
O1B | 0.10195 (12) | 0.2500 | 0.30920 (6) | 0.0113 (2) | |
O1A | 0.11570 (12) | 0.7500 | 0.02161 (6) | 0.0132 (3) | |
O2B | −0.10902 (13) | 0.2500 | 0.32425 (7) | 0.0233 (3) | |
O2A | 0.17059 (18) | 0.7205 (10) | −0.08458 (9) | 0.0253 (15) | 0.5 |
O3B | 0.39180 (12) | 0.2500 | 0.44805 (6) | 0.0111 (2) | |
O3A | 0.34526 (12) | 0.7500 | 0.18730 (6) | 0.0120 (3) | |
O4A | 0.55732 (14) | 0.7500 | 0.19630 (8) | 0.0263 (4) | |
O4B | 0.38006 (13) | 0.2500 | 0.55830 (7) | 0.0182 (3) | |
O5B | 0.40109 (12) | 0.2500 | 0.28824 (6) | 0.0121 (3) | |
O5A | 0.05126 (12) | 0.7500 | 0.18052 (6) | 0.0133 (3) | |
N1B | 0.14803 (14) | 0.2500 | 0.43438 (7) | 0.0096 (3) | |
N1A | 0.34951 (14) | 0.7500 | 0.06078 (8) | 0.0115 (3) | |
N2B | 0.27691 (9) | 0.55104 (16) | 0.36044 (5) | 0.0099 (2) | |
N2A | 0.18744 (9) | 0.44903 (16) | 0.11862 (5) | 0.0106 (2) | |
C1A | 0.19489 (19) | 0.7500 | −0.02550 (10) | 0.0191 (4) | |
C1B | 0.33304 (17) | 0.2500 | 0.50290 (9) | 0.0116 (3) | |
C2B | 0.18885 (17) | 0.2500 | 0.49647 (9) | 0.0114 (3) | |
C2A | 0.33379 (18) | 0.7500 | −0.00413 (9) | 0.0145 (4) | |
C3B | 0.10332 (18) | 0.2500 | 0.54760 (9) | 0.0156 (4) | |
H3BA | 0.1317 | 0.2500 | 0.5920 | 0.019* | |
C3A | 0.4378 (2) | 0.7500 | −0.04533 (10) | 0.0186 (4) | |
H3AA | 0.4274 | 0.7500 | −0.0917 | 0.022* | |
C4B | −0.02551 (19) | 0.2500 | 0.53191 (10) | 0.0178 (4) | |
H4BA | −0.0861 | 0.2500 | 0.5660 | 0.021* | |
C4A | 0.55810 (19) | 0.7500 | −0.01630 (11) | 0.0206 (4) | |
H4AA | 0.6310 | 0.7500 | −0.0432 | 0.025* | |
C5B | −0.06604 (18) | 0.2500 | 0.46662 (10) | 0.0157 (4) | |
H5BA | −0.1537 | 0.2500 | 0.4556 | 0.019* | |
C5A | 0.57227 (18) | 0.7500 | 0.05169 (11) | 0.0183 (4) | |
H5AA | 0.6540 | 0.7500 | 0.0717 | 0.022* | |
C6B | 0.02532 (17) | 0.2500 | 0.41808 (9) | 0.0114 (3) | |
C6A | 0.46371 (17) | 0.7500 | 0.08948 (9) | 0.0135 (4) | |
C7B | 0.00208 (17) | 0.2500 | 0.34383 (9) | 0.0127 (3) | |
C7A | 0.45721 (17) | 0.7500 | 0.16448 (9) | 0.0141 (4) | |
C11B | 0.21031 (11) | 0.65089 (18) | 0.31586 (6) | 0.0107 (2) | |
H11B | 0.1620 | 0.5849 | 0.2835 | 0.013* | |
C11A | 0.25161 (12) | 0.34864 (19) | 0.16410 (6) | 0.0129 (2) | |
H11A | 0.2982 | 0.4144 | 0.1972 | 0.015* | |
C12B | 0.34543 (11) | 0.65142 (18) | 0.40430 (6) | 0.0115 (2) | |
H12B | 0.3951 | 0.5856 | 0.4361 | 0.014* | |
C12A | 0.11868 (12) | 0.34903 (19) | 0.07512 (7) | 0.0157 (3) | |
H12A | 0.0686 | 0.4149 | 0.0435 | 0.019* | |
C21B | 0.60288 (13) | 0.4416 (2) | 0.33098 (7) | 0.0209 (3) | |
H21A | 0.6954 | 0.4467 | 0.3284 | 0.031* | |
H21B | 0.5669 | 0.5614 | 0.3148 | 0.031* | |
H21C | 0.5781 | 0.4221 | 0.3767 | 0.031* | |
C21A | −0.1608 (4) | 0.5556 (5) | 0.1942 (4) | 0.0179 (12)* | 0.46 (2) |
H21D | −0.2505 | 0.5546 | 0.1814 | 0.027* | 0.46 (2) |
H21E | −0.1201 | 0.4393 | 0.1783 | 0.027* | 0.46 (2) |
H21F | −0.1530 | 0.5616 | 0.2421 | 0.027* | 0.46 (2) |
C22A | −0.1502 (4) | 0.5609 (5) | 0.2133 (4) | 0.0196 (10)* | 0.54 (2) |
H22A | −0.2413 | 0.5458 | 0.2051 | 0.029* | 0.54 (2) |
H22B | −0.1068 | 0.4412 | 0.2036 | 0.029* | 0.54 (2) |
H22C | −0.1356 | 0.5949 | 0.2594 | 0.029* | 0.54 (2) |
U11 | U22 | U33 | U12 | U13 | U23 | |
Ni1A | 0.00710 (11) | 0.00803 (11) | 0.00981 (11) | 0.000 | −0.00020 (8) | 0.000 |
Ni1B | 0.00712 (11) | 0.00684 (11) | 0.00903 (11) | 0.000 | −0.00055 (8) | 0.000 |
S1B | 0.0106 (2) | 0.0141 (2) | 0.0116 (2) | 0.000 | 0.00228 (15) | 0.000 |
S1A | 0.0095 (2) | 0.0211 (2) | 0.0121 (2) | 0.000 | 0.00003 (15) | 0.000 |
O1B | 0.0099 (6) | 0.0118 (6) | 0.0122 (6) | 0.000 | −0.0019 (5) | 0.000 |
O1A | 0.0128 (6) | 0.0142 (6) | 0.0125 (6) | 0.000 | −0.0013 (5) | 0.000 |
O2B | 0.0098 (6) | 0.0403 (9) | 0.0198 (7) | 0.000 | −0.0042 (5) | 0.000 |
O2A | 0.0269 (9) | 0.038 (5) | 0.0115 (7) | −0.0012 (11) | −0.0023 (6) | −0.0008 (10) |
O3B | 0.0108 (6) | 0.0104 (6) | 0.0120 (6) | 0.000 | −0.0013 (5) | 0.000 |
O3A | 0.0105 (6) | 0.0127 (6) | 0.0129 (6) | 0.000 | −0.0007 (5) | 0.000 |
O4A | 0.0115 (7) | 0.0433 (10) | 0.0239 (8) | 0.000 | −0.0050 (6) | 0.000 |
O4B | 0.0181 (7) | 0.0235 (7) | 0.0129 (6) | 0.000 | −0.0057 (5) | 0.000 |
O5B | 0.0101 (6) | 0.0158 (6) | 0.0104 (6) | 0.000 | −0.0005 (5) | 0.000 |
O5A | 0.0079 (6) | 0.0187 (7) | 0.0133 (6) | 0.000 | 0.0002 (5) | 0.000 |
N1B | 0.0100 (7) | 0.0073 (7) | 0.0116 (7) | 0.000 | −0.0001 (5) | 0.000 |
N1A | 0.0115 (7) | 0.0093 (7) | 0.0135 (7) | 0.000 | 0.0014 (6) | 0.000 |
N2B | 0.0089 (5) | 0.0089 (5) | 0.0118 (5) | 0.0000 (4) | 0.0020 (4) | −0.0003 (4) |
N2A | 0.0091 (5) | 0.0101 (5) | 0.0128 (5) | 0.0004 (4) | 0.0015 (4) | −0.0001 (4) |
C1A | 0.0179 (9) | 0.0238 (10) | 0.0156 (9) | 0.000 | −0.0018 (7) | 0.000 |
C1B | 0.0131 (8) | 0.0067 (8) | 0.0151 (9) | 0.000 | −0.0019 (7) | 0.000 |
C2B | 0.0137 (8) | 0.0083 (8) | 0.0120 (8) | 0.000 | −0.0008 (7) | 0.000 |
C2A | 0.0166 (9) | 0.0123 (8) | 0.0145 (9) | 0.000 | 0.0023 (7) | 0.000 |
C3B | 0.0195 (9) | 0.0161 (9) | 0.0113 (8) | 0.000 | 0.0016 (7) | 0.000 |
C3A | 0.0233 (10) | 0.0171 (9) | 0.0155 (9) | 0.000 | 0.0057 (8) | 0.000 |
C4B | 0.0169 (9) | 0.0194 (10) | 0.0172 (9) | 0.000 | 0.0080 (7) | 0.000 |
C4A | 0.0169 (9) | 0.0183 (10) | 0.0268 (11) | 0.000 | 0.0123 (8) | 0.000 |
C5B | 0.0116 (8) | 0.0160 (9) | 0.0196 (9) | 0.000 | 0.0018 (7) | 0.000 |
C5A | 0.0113 (9) | 0.0159 (9) | 0.0278 (11) | 0.000 | 0.0037 (8) | 0.000 |
C6B | 0.0102 (8) | 0.0096 (8) | 0.0144 (8) | 0.000 | −0.0002 (7) | 0.000 |
C6A | 0.0118 (8) | 0.0098 (8) | 0.0190 (9) | 0.000 | 0.0010 (7) | 0.000 |
C7B | 0.0119 (8) | 0.0114 (8) | 0.0149 (9) | 0.000 | −0.0015 (7) | 0.000 |
C7A | 0.0111 (8) | 0.0123 (9) | 0.0188 (9) | 0.000 | −0.0011 (7) | 0.000 |
C11B | 0.0119 (5) | 0.0108 (6) | 0.0094 (5) | −0.0005 (5) | 0.0014 (4) | −0.0009 (5) |
C11A | 0.0169 (6) | 0.0122 (6) | 0.0095 (5) | −0.0007 (5) | 0.0000 (4) | −0.0009 (5) |
C12B | 0.0095 (5) | 0.0106 (6) | 0.0144 (6) | 0.0004 (5) | −0.0009 (4) | 0.0007 (5) |
C12A | 0.0121 (6) | 0.0122 (7) | 0.0226 (7) | 0.0006 (5) | −0.0067 (5) | 0.0009 (5) |
C21B | 0.0136 (6) | 0.0194 (7) | 0.0295 (7) | −0.0040 (5) | 0.0011 (5) | −0.0080 (6) |
Ni1A—N1A | 1.9788 (15) | C1A—O2Ai | 1.245 (3) |
Ni1A—O5A | 2.0313 (13) | C1A—C2A | 1.526 (3) |
Ni1A—O1A | 2.1032 (13) | C1B—C2B | 1.527 (2) |
Ni1A—N2Ai | 2.1186 (11) | C2B—C3B | 1.386 (3) |
Ni1A—N2A | 2.1186 (11) | C2A—C3A | 1.390 (3) |
Ni1A—O3A | 2.1191 (13) | C3B—C4B | 1.394 (3) |
Ni1B—N1B | 1.9804 (15) | C3B—H3BA | 0.9500 |
Ni1B—O5B | 2.0434 (13) | C3A—C4A | 1.395 (3) |
Ni1B—O3B | 2.1073 (13) | C3A—H3AA | 0.9500 |
Ni1B—N2B | 2.1172 (11) | C4B—C5B | 1.393 (3) |
Ni1B—N2Bii | 2.1173 (11) | C4B—H4BA | 0.9500 |
Ni1B—O1B | 2.1255 (12) | C4A—C5A | 1.391 (3) |
S1B—O5B | 1.5286 (13) | C4A—H4AA | 0.9500 |
S1B—C21Bii | 1.7786 (14) | C5B—C6B | 1.389 (3) |
S1B—C21B | 1.7786 (14) | C5B—H5BA | 0.9500 |
S1A—O5A | 1.5276 (13) | C5A—C6A | 1.388 (3) |
S1A—C21A | 1.713 (4) | C5A—H5AA | 0.9500 |
S1A—C21Ai | 1.713 (4) | C6B—C7B | 1.530 (3) |
S1A—C22A | 1.836 (4) | C6A—C7A | 1.530 (3) |
S1A—C22Ai | 1.836 (4) | C11B—C11Bi | 1.393 (3) |
O1B—C7B | 1.276 (2) | C11B—H11B | 0.9500 |
O1A—C1A | 1.280 (2) | C11A—C11Aii | 1.387 (3) |
O2B—C7B | 1.235 (2) | C11A—H11A | 0.9500 |
O2A—O2Ai | 0.414 (15) | C12B—C12Bi | 1.386 (3) |
O2A—C1A | 1.245 (3) | C12B—H12B | 0.9500 |
O3B—C1B | 1.284 (2) | C12A—C12Aii | 1.392 (3) |
O3A—C7A | 1.276 (2) | C12A—H12A | 0.9500 |
O4A—C7A | 1.234 (2) | C21B—H21A | 0.9800 |
O4B—C1B | 1.228 (2) | C21B—H21B | 0.9800 |
N1B—C2B | 1.332 (2) | C21B—H21C | 0.9800 |
N1B—C6B | 1.334 (2) | C21A—H21D | 0.9800 |
N1A—C2A | 1.331 (2) | C21A—H21E | 0.9800 |
N1A—C6A | 1.335 (2) | C21A—H21F | 0.9800 |
N2B—C11B | 1.3408 (16) | C22A—H22A | 0.9800 |
N2B—C12B | 1.3438 (16) | C22A—H22B | 0.9800 |
N2A—C12A | 1.3388 (17) | C22A—H22C | 0.9800 |
N2A—C11A | 1.3423 (16) | ||
N1A—Ni1A—O5A | 174.81 (6) | N1B—C2B—C3B | 120.45 (17) |
N1A—Ni1A—O1A | 78.58 (6) | N1B—C2B—C1B | 113.16 (15) |
O5A—Ni1A—O1A | 106.61 (5) | C3B—C2B—C1B | 126.39 (17) |
N1A—Ni1A—N2Ai | 92.98 (3) | N1A—C2A—C3A | 120.61 (18) |
O5A—Ni1A—N2Ai | 87.08 (3) | N1A—C2A—C1A | 113.10 (16) |
O1A—Ni1A—N2Ai | 90.06 (3) | C3A—C2A—C1A | 126.30 (18) |
N1A—Ni1A—N2A | 92.98 (3) | C2B—C3B—C4B | 118.06 (17) |
O5A—Ni1A—N2A | 87.08 (3) | C2B—C3B—H3BA | 121.0 |
O1A—Ni1A—N2A | 90.06 (3) | C4B—C3B—H3BA | 121.0 |
N2Ai—Ni1A—N2A | 173.95 (6) | C2A—C3A—C4A | 117.80 (18) |
N1A—Ni1A—O3A | 77.89 (6) | C2A—C3A—H3AA | 121.1 |
O5A—Ni1A—O3A | 96.92 (5) | C4A—C3A—H3AA | 121.1 |
O1A—Ni1A—O3A | 156.48 (5) | C5B—C4B—C3B | 120.50 (17) |
N2Ai—Ni1A—O3A | 91.15 (3) | C5B—C4B—H4BA | 119.8 |
N2A—Ni1A—O3A | 91.15 (3) | C3B—C4B—H4BA | 119.8 |
N1B—Ni1B—O5B | 178.13 (6) | C5A—C4A—C3A | 120.61 (18) |
N1B—Ni1B—O3B | 78.45 (6) | C5A—C4A—H4AA | 119.7 |
O5B—Ni1B—O3B | 103.42 (5) | C3A—C4A—H4AA | 119.7 |
N1B—Ni1B—N2B | 91.65 (3) | C6B—C5B—C4B | 118.12 (17) |
O5B—Ni1B—N2B | 88.32 (3) | C6B—C5B—H5BA | 120.9 |
O3B—Ni1B—N2B | 91.06 (3) | C4B—C5B—H5BA | 120.9 |
N1B—Ni1B—N2Bii | 91.65 (3) | C6A—C5A—C4A | 118.14 (18) |
O5B—Ni1B—N2Bii | 88.32 (3) | C6A—C5A—H5AA | 120.9 |
O3B—Ni1B—N2Bii | 91.06 (3) | C4A—C5A—H5AA | 120.9 |
N2B—Ni1B—N2Bii | 176.38 (6) | N1B—C6B—C5B | 120.23 (17) |
N1B—Ni1B—O1B | 78.15 (6) | N1B—C6B—C7B | 112.99 (15) |
O5B—Ni1B—O1B | 99.97 (5) | C5B—C6B—C7B | 126.78 (16) |
O3B—Ni1B—O1B | 156.61 (5) | N1A—C6A—C5A | 120.34 (18) |
N2B—Ni1B—O1B | 89.61 (3) | N1A—C6A—C7A | 112.76 (16) |
N2Bii—Ni1B—O1B | 89.61 (3) | C5A—C6A—C7A | 126.89 (17) |
O5B—S1B—C21Bii | 106.82 (6) | O2B—C7B—O1B | 127.59 (18) |
O5B—S1B—C21B | 106.82 (6) | O2B—C7B—C6B | 117.43 (16) |
C21Bii—S1B—C21B | 98.42 (11) | O1B—C7B—C6B | 114.98 (15) |
O5A—S1A—C21A | 109.0 (2) | O4A—C7A—O3A | 126.94 (18) |
O5A—S1A—C21Ai | 109.0 (2) | O4A—C7A—C6A | 118.47 (17) |
C21A—S1A—C21Ai | 105.8 (3) | O3A—C7A—C6A | 114.59 (16) |
O5A—S1A—C22A | 101.00 (18) | N2B—C11B—C11Bi | 121.57 (7) |
O5A—S1A—C22Ai | 101.00 (18) | N2B—C11B—H11B | 119.2 |
C22A—S1A—C22Ai | 92.8 (3) | C11Bi—C11B—H11B | 119.2 |
C7B—O1B—Ni1B | 115.04 (11) | N2A—C11A—C11Aii | 121.72 (7) |
C1A—O1A—Ni1A | 115.10 (12) | N2A—C11A—H11A | 119.1 |
O2Ai—O2A—C1A | 80.4 (3) | C11Aii—C11A—H11A | 119.1 |
C1B—O3B—Ni1B | 115.23 (11) | N2B—C12B—C12Bi | 121.67 (7) |
C7A—O3A—Ni1A | 115.61 (12) | N2B—C12B—H12B | 119.2 |
S1B—O5B—Ni1B | 136.06 (8) | C12Bi—C12B—H12B | 119.2 |
S1A—O5A—Ni1A | 124.34 (8) | N2A—C12A—C12Aii | 121.68 (7) |
C2B—N1B—C6B | 122.64 (16) | N2A—C12A—H12A | 119.2 |
C2B—N1B—Ni1B | 118.53 (12) | C12Aii—C12A—H12A | 119.2 |
C6B—N1B—Ni1B | 118.83 (12) | S1B—C21B—H21A | 109.5 |
C2A—N1A—C6A | 122.50 (16) | S1B—C21B—H21B | 109.5 |
C2A—N1A—Ni1A | 118.36 (13) | H21A—C21B—H21B | 109.5 |
C6A—N1A—Ni1A | 119.14 (13) | S1B—C21B—H21C | 109.5 |
C11B—N2B—C12B | 116.75 (11) | H21A—C21B—H21C | 109.5 |
C11B—N2B—Ni1B | 122.56 (8) | H21B—C21B—H21C | 109.5 |
C12B—N2B—Ni1B | 120.69 (8) | S1A—C21A—H21D | 109.5 |
C12A—N2A—C11A | 116.53 (12) | S1A—C21A—H21E | 109.5 |
C12A—N2A—Ni1A | 122.38 (9) | H21D—C21A—H21E | 109.5 |
C11A—N2A—Ni1A | 121.09 (9) | S1A—C21A—H21F | 109.5 |
O2A—C1A—O2Ai | 19.2 (7) | H21D—C21A—H21F | 109.5 |
O2A—C1A—O1A | 126.5 (2) | H21E—C21A—H21F | 109.5 |
O2Ai—C1A—O1A | 126.5 (2) | S1A—C22A—H22A | 109.5 |
O2A—C1A—C2A | 117.57 (19) | S1A—C22A—H22B | 109.5 |
O2Ai—C1A—C2A | 117.57 (19) | H22A—C22A—H22B | 109.5 |
O1A—C1A—C2A | 114.86 (17) | S1A—C22A—H22C | 109.5 |
O4B—C1B—O3B | 127.24 (17) | H22A—C22A—H22C | 109.5 |
O4B—C1B—C2B | 118.13 (16) | H22B—C22A—H22C | 109.5 |
O3B—C1B—C2B | 114.63 (15) |
Symmetry codes: (i) x, −y+3/2, z; (ii) x, −y+1/2, z. |
D—H···A | D—H | H···A | D···A | D—H···A |
C11B—H11B···O1B | 0.95 | 2.50 | 3.0442 (13) | 117 |
C11B—H11B···O5A | 0.95 | 2.66 | 3.2871 (18) | 124 |
C11A—H11A···O3A | 0.95 | 2.42 | 3.0252 (14) | 121 |
C11A—H11A···O5B | 0.95 | 2.43 | 3.0462 (17) | 122 |
C12B—H12B···O3B | 0.95 | 2.37 | 2.9978 (13) | 123 |
C12A—H12A···O1A | 0.95 | 2.45 | 3.0221 (14) | 119 |
C12A—H12A···O1Aiii | 0.95 | 2.61 | 3.2230 (18) | 122 |
C21B—H21A···O2Biv | 0.98 | 2.49 | 3.3321 (19) | 144 |
C21A—H21D···O4Av | 0.98 | 2.47 | 3.277 (4) | 139 |
C21A—H21E···O2Aiii | 0.98 | 2.27 | 2.959 (9) | 126 |
C21A—H21E···O2Avi | 0.98 | 2.50 | 3.246 (9) | 132 |
C22A—H22A···O4Av | 0.98 | 2.57 | 3.377 (4) | 140 |
Symmetry codes: (iii) −x, −y+1, −z; (iv) x+1, −y+1/2, z; (v) x−1, −y+3/2, z; (vi) −x, y−1/2, −z. |
D—H···A | D—H | H···A | D···A | D—H···A |
C11B—H11B···O1B | 0.95 | 2.50 | 3.0442 (13) | 116.8 |
C11B—H11B···O5A | 0.95 | 2.66 | 3.2871 (18) | 124.3 |
C11A—H11A···O3A | 0.95 | 2.42 | 3.0252 (14) | 121.4 |
C11A—H11A···O5B | 0.95 | 2.43 | 3.0462 (17) | 122.2 |
C12B—H12B···O3B | 0.95 | 2.37 | 2.9978 (13) | 123.1 |
C12A—H12A···O1A | 0.95 | 2.45 | 3.0221 (14) | 118.6 |
C12A—H12A···O1Ai | 0.95 | 2.61 | 3.2230 (18) | 122.3 |
C21B—H21A···O2Bii | 0.98 | 2.49 | 3.3321 (19) | 144.1 |
C21A—H21D···O4Aiii | 0.98 | 2.47 | 3.277 (4) | 139.2 |
C21A—H21E···O2Ai | 0.98 | 2.27 | 2.959 (9) | 126.2 |
C21A—H21E···O2Aiv | 0.98 | 2.50 | 3.246 (9) | 132.3 |
C22A—H22A···O4Aiii | 0.98 | 2.57 | 3.377 (4) | 139.5 |
Symmetry codes: (i) −x, −y+1, −z; (ii) x+1, −y+1/2, z; (iii) x−1, −y+3/2, z; (iv) −x, y−1/2, −z. |
Experimental details
Crystal data | |
Chemical formula | [Ni(C7H3NO4)(C4H4N2)(C2H6OS)] |
Mr | 382.03 |
Crystal system, space group | Monoclinic, P21/m |
Temperature (K) | 100 |
a, b, c (Å) | 10.5631 (7), 7.0296 (4), 20.3710 (13) |
β (°) | 90.6447 (11) |
V (Å3) | 1512.54 (16) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 1.45 |
Crystal size (mm) | 0.37 × 0.15 × 0.05 |
Data collection | |
Diffractometer | Bruker APEXII DUO CCD |
Absorption correction | Analytical based on measured indexed crystal faces; XPREP (Bruker, 2014) |
Tmin, Tmax | 0.730, 0.965 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 56634, 3756, 3549 |
Rint | 0.026 |
(sin θ/λ)max (Å−1) | 0.650 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.020, 0.055, 1.07 |
No. of reflections | 3756 |
No. of parameters | 256 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.43, −0.31 |
Computer programs: APEX2 (Bruker, 2014), SAINT (Bruker, 2014), SHELXT (Sheldrick, 2015a), SHELXL2014 (Sheldrick, 2015b), XP (Bruker, 2014), publCIF (Westrip, 2010).
Acknowledgements
CL wishes to acknowledge financial support for this work from the Research & Development Corporation of Newfoundland and Labrador. KAA wishes to acknowledge the National Science Foundation and the University of Florida for funding the purchase of the X-ray equipment.
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