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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 72| Part 5| May 2016| Pages 768-771

Crystal structure of catena-poly[[(di­methyl sulfoxide-κO)(pyridine-2,6-di­carboxyl­ato-κ3O,N,O′)nickel(II)]-μ-pyrazine-κ2N:N′]

CROSSMARK_Color_square_no_text.svg

aDepartment 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

Edited by M. Weil, Vienna University of Technology, Austria (Received 18 April 2016; accepted 26 April 2016; online 29 April 2016)

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 ππ 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 ππ 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 ππ 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.

1. Chemical context

In general, ππ inter­actions are considered important mechanisms for mol­ecular recognition and may function as structure-directing factors in the design and preparation of coordination polymers. However, ππ 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[Liu, C., Čižmár, E., Park, J. H., Abboud, K. A., Meisel, M. W. & Talham, D. R. (2011). Polyhedron, 30, 1420-1424.]). 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 ππ stacking and C—H⋯π inter­actions involving two different aromatic mol­ecules, viz. pyridine and pyrazine.

[Scheme 1]

2. Structural commentary

The asymmetric unit 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[link]). 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.

[Figure 1]
Figure 1
A view of the asymmetric unit of the title compound, showing the atom labelling. Displacement ellipsoids are drawn at the 50% probability level. All disordered components are shown.

3. Supra­molecular features

In the crystal, two NiII chains form a double-chain structure via ππ stacking between their pyridine moieties (Fig. 2[link]). 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 ππ 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[Zheng, Y. Q., Sun, J. & Lin, J. L. (2000). Z. Anorg. Allg. Chem. 626, 1501-1504.]; Nawrot et al., 2015[Nawrot, I., Machura, B. & Kruszynski, R. (2015). CrystEngComm, 17, 830-845.]). Within the double-chain, two ππ stacked pyridine moieties are also parallel-shifted by 1.50422 (8) Å, consistent with values obtained from computational studies (Huber et al., 2014[Huber, R. G., Margreiter, M. A., Fuchs, J. E., von Grafenstein, S., Tautermann, C. S., Liedl, K. R. & Fox, T. (2014). J. Chem. Inf. Model. 54, 1371-1379.]). Although ππ 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 ππ stacking as a potential strategy for incorporating ππ stacking in the design and synthesis of coordination polymers.

[Figure 2]
Figure 2
A view of the double-chain structure of the title compound running parallel to [010].

Accompanying the ππ 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[Tiekink, E. R. T. & Zuckerman-Schpector, J. (2012). Editors. Importance of Pi-interaction in Crystal Engineering: Frontiers in Crystal Engineering, 2nd ed., pp. 111-112. London: Wiley.]), contributing additional stability to the double-chain structure. The concurrence of both parallel ππ 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[Tiekink, E. R. T. & Zuckerman-Schpector, J. (2012). Editors. Importance of Pi-interaction in Crystal Engineering: Frontiers in Crystal Engineering, 2nd ed., pp. 111-112. London: Wiley.]). We are aware of only one other example of a coordination polymer exhibiting this feature (Felloni et al., 2010[Felloni, M., Blake, A. J., Hubberstey, P., Teat, S. J., Wilson, C. & Schröder, M. (2010). CrystEngComm, 12, 1576-1589.]). 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[Mishra, B. K. & Sathyamurthy, N. (2005). J. Phys. Chem. A, 109, 6-8.]; Hohenstein & Sherrill, 2009[Hohenstein, E. G. & Sherrill, C. D. (2009). J. Phys. Chem. A, 113, 878-886.]; Huber et al., 2014[Huber, R. G., Margreiter, M. A., Fuchs, J. E., von Grafenstein, S., Tautermann, C. S., Liedl, K. R. & Fox, T. (2014). J. Chem. Inf. Model. 54, 1371-1379.]).

In contrast to the ππ 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[link]), 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[link].

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA 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⋯O1Ai 0.95 2.61 3.2230 (18) 122
C21B—H21A⋯O2Bii 0.98 2.49 3.3321 (19) 144
C21A—H21D⋯O4Aiii 0.98 2.47 3.277 (4) 139
C21A—H21E⋯O2Ai 0.98 2.27 2.959 (9) 126
C21A—H21E⋯O2Aiv 0.98 2.50 3.246 (9) 132
C22A—H22A⋯O4Aiii 0.98 2.57 3.377 (4) 140
Symmetry codes: (i) -x, -y+1, -z; (ii) [x+1, -y+{\script{1\over 2}}, z]; (iii) [x-1, -y+{\script{3\over 2}}, z]; (iv) [-x, y-{\script{1\over 2}}, -z].
[Figure 3]
Figure 3
Crystal packing of the title compound, showing hydrogen-bonding inter­actions as dashed lines.

In summary, a separation of dissimilar inter­actions can be observed between the non-covalent lipophilic ππ 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 refinement details are summarized in Table 2[link]. 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.

Table 2
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)
V3) 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[Bruker (2014). APEX2, SAINT, XPREP and XP. Bruker Inc., Madison, Wisconsin, USA.])
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−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 and SAINT (Bruker, 2014[Bruker (2014). APEX2, SAINT, XPREP and XP. Bruker Inc., Madison, Wisconsin, USA.]), SHELXT (Sheldrick, 2015a[Sheldrick, G. M. (2015a). Acta Cryst. A71, 3-8.]), SHELXL2014 (Sheldrick, 2015b[Sheldrick, G. M. (2015b). Acta Cryst. C71, 3-8.]), XP (Bruker, 2014[Bruker (2014). APEX2, SAINT, XPREP and XP. Bruker Inc., Madison, Wisconsin, USA.]) and publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).

Supporting information


Chemical context top

In general, ππ inter­actions are considered important mechanisms for molecular recognition and may function as structure-directing factors in the design and preparation of coordination polymers. However, ππ 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 ππ stacking and C—H···π inter­actions involving two different aromatic molecules, viz. pyridine and pyrazine.

Structural commentary top

The asymmetric unit 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 SO bonds. In the chains, the Ni—Ni distance across bridging pyrazine is 7.0296 (4) Å, i.e. the length of the b axis.

Supra­molecular features top

In the crystal, two NiII chains form a double-chain structure via ππ 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 ππ 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 ππ stacked pyridine moieties are also parallel-shifted by 1.50422 (8) Å, consistent with values obtained from computational studies (Huber et al., 2014). Although ππ 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 ππ stacking as a potential strategy for incorporating ππ stacking in the design and synthesis of coordination polymers.

Accompanying the ππ 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 ππ 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 ππ 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 ππ 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.

Synthesis and crystallization top

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 (CO), 1367.91 (C—O), 950.92 (SO), 480.64 (bridging pyrazine).

Refinement top

Crystal data, data collection and structure refinement 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.

Structure description top

In general, ππ inter­actions are considered important mechanisms for molecular recognition and may function as structure-directing factors in the design and preparation of coordination polymers. However, ππ 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 ππ stacking and C—H···π inter­actions involving two different aromatic molecules, viz. pyridine and pyrazine.

The asymmetric unit 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 SO bonds. In the chains, the Ni—Ni distance across bridging pyrazine is 7.0296 (4) Å, i.e. the length of the b axis.

In the crystal, two NiII chains form a double-chain structure via ππ 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 ππ 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 ππ stacked pyridine moieties are also parallel-shifted by 1.50422 (8) Å, consistent with values obtained from computational studies (Huber et al., 2014). Although ππ 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 ππ stacking as a potential strategy for incorporating ππ stacking in the design and synthesis of coordination polymers.

Accompanying the ππ 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 ππ 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 ππ 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 ππ 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.

Synthesis and crystallization top

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 (CO), 1367.91 (C—O), 950.92 (SO), 480.64 (bridging pyrazine).

Refinement details top

Crystal data, data collection and structure refinement 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.

Computing details top

Data collection: APEX2 (Bruker, 2014); cell refinement: 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).

Figures top
[Figure 1] 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.
[Figure 2] Fig. 2. A view of the double-chain structure of the title compound running parallel to [010].
[Figure 3] Fig. 3. Crystal packing of the title compound, showing hydrogen-bonding interactions as dashed lines.
catena-Poly[[(dimethyl sulfoxide-κO)(pyridine-2,6-dicarboxylato-κ3O,N,O')nickel(II)]-µ-pyrazine-κ2N:N'] top
Crystal data top
[Ni(C7H3NO4)(C4H4N2)(C2H6OS)]F(000) = 784
Mr = 382.03Dx = 1.678 Mg m3
Monoclinic, P21/mMo Kα radiation, λ = 0.71073 Å
a = 10.5631 (7) ÅCell parameters from 9922 reflections
b = 7.0296 (4) Åθ = 2.0–28.0°
c = 20.3710 (13) ŵ = 1.45 mm1
β = 90.6447 (11)°T = 100 K
V = 1512.54 (16) Å3Needle, green
Z = 40.37 × 0.15 × 0.05 mm
Data collection top
Bruker APEXII DUO CCD
diffractometer
3549 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.026
phi and ω scansθmax = 27.5°, θmin = 1.0°
Absorption correction: analytical
based on measured indexed crystal faces; XPREP (Bruker, 2014)
h = 1313
Tmin = 0.730, Tmax = 0.965k = 99
56634 measured reflectionsl = 2626
3756 independent reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.020Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.055H-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 parametersΔρmax = 0.43 e Å3
0 restraintsΔρmin = 0.31 e Å3
Crystal data top
[Ni(C7H3NO4)(C4H4N2)(C2H6OS)]V = 1512.54 (16) Å3
Mr = 382.03Z = 4
Monoclinic, P21/mMo Kα radiation
a = 10.5631 (7) ŵ = 1.45 mm1
b = 7.0296 (4) ÅT = 100 K
c = 20.3710 (13) Å0.37 × 0.15 × 0.05 mm
β = 90.6447 (11)°
Data collection top
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 = 0.965Rint = 0.026
56634 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0200 restraints
wR(F2) = 0.055H-atom parameters constrained
S = 1.07Δρmax = 0.43 e Å3
3756 reflectionsΔρmin = 0.31 e Å3
256 parameters
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
Ni1A0.19703 (2)0.75000.11633 (2)0.00831 (6)
Ni1B0.27491 (2)0.25000.36354 (2)0.00767 (6)
S1B0.54518 (4)0.25000.28209 (2)0.01208 (9)
S1A0.08847 (4)0.75000.16036 (2)0.01425 (10)
O1B0.10195 (12)0.25000.30920 (6)0.0113 (2)
O1A0.11570 (12)0.75000.02161 (6)0.0132 (3)
O2B0.10902 (13)0.25000.32425 (7)0.0233 (3)
O2A0.17059 (18)0.7205 (10)0.08458 (9)0.0253 (15)0.5
O3B0.39180 (12)0.25000.44805 (6)0.0111 (2)
O3A0.34526 (12)0.75000.18730 (6)0.0120 (3)
O4A0.55732 (14)0.75000.19630 (8)0.0263 (4)
O4B0.38006 (13)0.25000.55830 (7)0.0182 (3)
O5B0.40109 (12)0.25000.28824 (6)0.0121 (3)
O5A0.05126 (12)0.75000.18052 (6)0.0133 (3)
N1B0.14803 (14)0.25000.43438 (7)0.0096 (3)
N1A0.34951 (14)0.75000.06078 (8)0.0115 (3)
N2B0.27691 (9)0.55104 (16)0.36044 (5)0.0099 (2)
N2A0.18744 (9)0.44903 (16)0.11862 (5)0.0106 (2)
C1A0.19489 (19)0.75000.02550 (10)0.0191 (4)
C1B0.33304 (17)0.25000.50290 (9)0.0116 (3)
C2B0.18885 (17)0.25000.49647 (9)0.0114 (3)
C2A0.33379 (18)0.75000.00413 (9)0.0145 (4)
C3B0.10332 (18)0.25000.54760 (9)0.0156 (4)
H3BA0.13170.25000.59200.019*
C3A0.4378 (2)0.75000.04533 (10)0.0186 (4)
H3AA0.42740.75000.09170.022*
C4B0.02551 (19)0.25000.53191 (10)0.0178 (4)
H4BA0.08610.25000.56600.021*
C4A0.55810 (19)0.75000.01630 (11)0.0206 (4)
H4AA0.63100.75000.04320.025*
C5B0.06604 (18)0.25000.46662 (10)0.0157 (4)
H5BA0.15370.25000.45560.019*
C5A0.57227 (18)0.75000.05169 (11)0.0183 (4)
H5AA0.65400.75000.07170.022*
C6B0.02532 (17)0.25000.41808 (9)0.0114 (3)
C6A0.46371 (17)0.75000.08948 (9)0.0135 (4)
C7B0.00208 (17)0.25000.34383 (9)0.0127 (3)
C7A0.45721 (17)0.75000.16448 (9)0.0141 (4)
C11B0.21031 (11)0.65089 (18)0.31586 (6)0.0107 (2)
H11B0.16200.58490.28350.013*
C11A0.25161 (12)0.34864 (19)0.16410 (6)0.0129 (2)
H11A0.29820.41440.19720.015*
C12B0.34543 (11)0.65142 (18)0.40430 (6)0.0115 (2)
H12B0.39510.58560.43610.014*
C12A0.11868 (12)0.34903 (19)0.07512 (7)0.0157 (3)
H12A0.06860.41490.04350.019*
C21B0.60288 (13)0.4416 (2)0.33098 (7)0.0209 (3)
H21A0.69540.44670.32840.031*
H21B0.56690.56140.31480.031*
H21C0.57810.42210.37670.031*
C21A0.1608 (4)0.5556 (5)0.1942 (4)0.0179 (12)*0.46 (2)
H21D0.25050.55460.18140.027*0.46 (2)
H21E0.12010.43930.17830.027*0.46 (2)
H21F0.15300.56160.24210.027*0.46 (2)
C22A0.1502 (4)0.5609 (5)0.2133 (4)0.0196 (10)*0.54 (2)
H22A0.24130.54580.20510.029*0.54 (2)
H22B0.10680.44120.20360.029*0.54 (2)
H22C0.13560.59490.25940.029*0.54 (2)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ni1A0.00710 (11)0.00803 (11)0.00981 (11)0.0000.00020 (8)0.000
Ni1B0.00712 (11)0.00684 (11)0.00903 (11)0.0000.00055 (8)0.000
S1B0.0106 (2)0.0141 (2)0.0116 (2)0.0000.00228 (15)0.000
S1A0.0095 (2)0.0211 (2)0.0121 (2)0.0000.00003 (15)0.000
O1B0.0099 (6)0.0118 (6)0.0122 (6)0.0000.0019 (5)0.000
O1A0.0128 (6)0.0142 (6)0.0125 (6)0.0000.0013 (5)0.000
O2B0.0098 (6)0.0403 (9)0.0198 (7)0.0000.0042 (5)0.000
O2A0.0269 (9)0.038 (5)0.0115 (7)0.0012 (11)0.0023 (6)0.0008 (10)
O3B0.0108 (6)0.0104 (6)0.0120 (6)0.0000.0013 (5)0.000
O3A0.0105 (6)0.0127 (6)0.0129 (6)0.0000.0007 (5)0.000
O4A0.0115 (7)0.0433 (10)0.0239 (8)0.0000.0050 (6)0.000
O4B0.0181 (7)0.0235 (7)0.0129 (6)0.0000.0057 (5)0.000
O5B0.0101 (6)0.0158 (6)0.0104 (6)0.0000.0005 (5)0.000
O5A0.0079 (6)0.0187 (7)0.0133 (6)0.0000.0002 (5)0.000
N1B0.0100 (7)0.0073 (7)0.0116 (7)0.0000.0001 (5)0.000
N1A0.0115 (7)0.0093 (7)0.0135 (7)0.0000.0014 (6)0.000
N2B0.0089 (5)0.0089 (5)0.0118 (5)0.0000 (4)0.0020 (4)0.0003 (4)
N2A0.0091 (5)0.0101 (5)0.0128 (5)0.0004 (4)0.0015 (4)0.0001 (4)
C1A0.0179 (9)0.0238 (10)0.0156 (9)0.0000.0018 (7)0.000
C1B0.0131 (8)0.0067 (8)0.0151 (9)0.0000.0019 (7)0.000
C2B0.0137 (8)0.0083 (8)0.0120 (8)0.0000.0008 (7)0.000
C2A0.0166 (9)0.0123 (8)0.0145 (9)0.0000.0023 (7)0.000
C3B0.0195 (9)0.0161 (9)0.0113 (8)0.0000.0016 (7)0.000
C3A0.0233 (10)0.0171 (9)0.0155 (9)0.0000.0057 (8)0.000
C4B0.0169 (9)0.0194 (10)0.0172 (9)0.0000.0080 (7)0.000
C4A0.0169 (9)0.0183 (10)0.0268 (11)0.0000.0123 (8)0.000
C5B0.0116 (8)0.0160 (9)0.0196 (9)0.0000.0018 (7)0.000
C5A0.0113 (9)0.0159 (9)0.0278 (11)0.0000.0037 (8)0.000
C6B0.0102 (8)0.0096 (8)0.0144 (8)0.0000.0002 (7)0.000
C6A0.0118 (8)0.0098 (8)0.0190 (9)0.0000.0010 (7)0.000
C7B0.0119 (8)0.0114 (8)0.0149 (9)0.0000.0015 (7)0.000
C7A0.0111 (8)0.0123 (9)0.0188 (9)0.0000.0011 (7)0.000
C11B0.0119 (5)0.0108 (6)0.0094 (5)0.0005 (5)0.0014 (4)0.0009 (5)
C11A0.0169 (6)0.0122 (6)0.0095 (5)0.0007 (5)0.0000 (4)0.0009 (5)
C12B0.0095 (5)0.0106 (6)0.0144 (6)0.0004 (5)0.0009 (4)0.0007 (5)
C12A0.0121 (6)0.0122 (7)0.0226 (7)0.0006 (5)0.0067 (5)0.0009 (5)
C21B0.0136 (6)0.0194 (7)0.0295 (7)0.0040 (5)0.0011 (5)0.0080 (6)
Geometric parameters (Å, º) top
Ni1A—N1A1.9788 (15)C1A—O2Ai1.245 (3)
Ni1A—O5A2.0313 (13)C1A—C2A1.526 (3)
Ni1A—O1A2.1032 (13)C1B—C2B1.527 (2)
Ni1A—N2Ai2.1186 (11)C2B—C3B1.386 (3)
Ni1A—N2A2.1186 (11)C2A—C3A1.390 (3)
Ni1A—O3A2.1191 (13)C3B—C4B1.394 (3)
Ni1B—N1B1.9804 (15)C3B—H3BA0.9500
Ni1B—O5B2.0434 (13)C3A—C4A1.395 (3)
Ni1B—O3B2.1073 (13)C3A—H3AA0.9500
Ni1B—N2B2.1172 (11)C4B—C5B1.393 (3)
Ni1B—N2Bii2.1173 (11)C4B—H4BA0.9500
Ni1B—O1B2.1255 (12)C4A—C5A1.391 (3)
S1B—O5B1.5286 (13)C4A—H4AA0.9500
S1B—C21Bii1.7786 (14)C5B—C6B1.389 (3)
S1B—C21B1.7786 (14)C5B—H5BA0.9500
S1A—O5A1.5276 (13)C5A—C6A1.388 (3)
S1A—C21A1.713 (4)C5A—H5AA0.9500
S1A—C21Ai1.713 (4)C6B—C7B1.530 (3)
S1A—C22A1.836 (4)C6A—C7A1.530 (3)
S1A—C22Ai1.836 (4)C11B—C11Bi1.393 (3)
O1B—C7B1.276 (2)C11B—H11B0.9500
O1A—C1A1.280 (2)C11A—C11Aii1.387 (3)
O2B—C7B1.235 (2)C11A—H11A0.9500
O2A—O2Ai0.414 (15)C12B—C12Bi1.386 (3)
O2A—C1A1.245 (3)C12B—H12B0.9500
O3B—C1B1.284 (2)C12A—C12Aii1.392 (3)
O3A—C7A1.276 (2)C12A—H12A0.9500
O4A—C7A1.234 (2)C21B—H21A0.9800
O4B—C1B1.228 (2)C21B—H21B0.9800
N1B—C2B1.332 (2)C21B—H21C0.9800
N1B—C6B1.334 (2)C21A—H21D0.9800
N1A—C2A1.331 (2)C21A—H21E0.9800
N1A—C6A1.335 (2)C21A—H21F0.9800
N2B—C11B1.3408 (16)C22A—H22A0.9800
N2B—C12B1.3438 (16)C22A—H22B0.9800
N2A—C12A1.3388 (17)C22A—H22C0.9800
N2A—C11A1.3423 (16)
N1A—Ni1A—O5A174.81 (6)N1B—C2B—C3B120.45 (17)
N1A—Ni1A—O1A78.58 (6)N1B—C2B—C1B113.16 (15)
O5A—Ni1A—O1A106.61 (5)C3B—C2B—C1B126.39 (17)
N1A—Ni1A—N2Ai92.98 (3)N1A—C2A—C3A120.61 (18)
O5A—Ni1A—N2Ai87.08 (3)N1A—C2A—C1A113.10 (16)
O1A—Ni1A—N2Ai90.06 (3)C3A—C2A—C1A126.30 (18)
N1A—Ni1A—N2A92.98 (3)C2B—C3B—C4B118.06 (17)
O5A—Ni1A—N2A87.08 (3)C2B—C3B—H3BA121.0
O1A—Ni1A—N2A90.06 (3)C4B—C3B—H3BA121.0
N2Ai—Ni1A—N2A173.95 (6)C2A—C3A—C4A117.80 (18)
N1A—Ni1A—O3A77.89 (6)C2A—C3A—H3AA121.1
O5A—Ni1A—O3A96.92 (5)C4A—C3A—H3AA121.1
O1A—Ni1A—O3A156.48 (5)C5B—C4B—C3B120.50 (17)
N2Ai—Ni1A—O3A91.15 (3)C5B—C4B—H4BA119.8
N2A—Ni1A—O3A91.15 (3)C3B—C4B—H4BA119.8
N1B—Ni1B—O5B178.13 (6)C5A—C4A—C3A120.61 (18)
N1B—Ni1B—O3B78.45 (6)C5A—C4A—H4AA119.7
O5B—Ni1B—O3B103.42 (5)C3A—C4A—H4AA119.7
N1B—Ni1B—N2B91.65 (3)C6B—C5B—C4B118.12 (17)
O5B—Ni1B—N2B88.32 (3)C6B—C5B—H5BA120.9
O3B—Ni1B—N2B91.06 (3)C4B—C5B—H5BA120.9
N1B—Ni1B—N2Bii91.65 (3)C6A—C5A—C4A118.14 (18)
O5B—Ni1B—N2Bii88.32 (3)C6A—C5A—H5AA120.9
O3B—Ni1B—N2Bii91.06 (3)C4A—C5A—H5AA120.9
N2B—Ni1B—N2Bii176.38 (6)N1B—C6B—C5B120.23 (17)
N1B—Ni1B—O1B78.15 (6)N1B—C6B—C7B112.99 (15)
O5B—Ni1B—O1B99.97 (5)C5B—C6B—C7B126.78 (16)
O3B—Ni1B—O1B156.61 (5)N1A—C6A—C5A120.34 (18)
N2B—Ni1B—O1B89.61 (3)N1A—C6A—C7A112.76 (16)
N2Bii—Ni1B—O1B89.61 (3)C5A—C6A—C7A126.89 (17)
O5B—S1B—C21Bii106.82 (6)O2B—C7B—O1B127.59 (18)
O5B—S1B—C21B106.82 (6)O2B—C7B—C6B117.43 (16)
C21Bii—S1B—C21B98.42 (11)O1B—C7B—C6B114.98 (15)
O5A—S1A—C21A109.0 (2)O4A—C7A—O3A126.94 (18)
O5A—S1A—C21Ai109.0 (2)O4A—C7A—C6A118.47 (17)
C21A—S1A—C21Ai105.8 (3)O3A—C7A—C6A114.59 (16)
O5A—S1A—C22A101.00 (18)N2B—C11B—C11Bi121.57 (7)
O5A—S1A—C22Ai101.00 (18)N2B—C11B—H11B119.2
C22A—S1A—C22Ai92.8 (3)C11Bi—C11B—H11B119.2
C7B—O1B—Ni1B115.04 (11)N2A—C11A—C11Aii121.72 (7)
C1A—O1A—Ni1A115.10 (12)N2A—C11A—H11A119.1
O2Ai—O2A—C1A80.4 (3)C11Aii—C11A—H11A119.1
C1B—O3B—Ni1B115.23 (11)N2B—C12B—C12Bi121.67 (7)
C7A—O3A—Ni1A115.61 (12)N2B—C12B—H12B119.2
S1B—O5B—Ni1B136.06 (8)C12Bi—C12B—H12B119.2
S1A—O5A—Ni1A124.34 (8)N2A—C12A—C12Aii121.68 (7)
C2B—N1B—C6B122.64 (16)N2A—C12A—H12A119.2
C2B—N1B—Ni1B118.53 (12)C12Aii—C12A—H12A119.2
C6B—N1B—Ni1B118.83 (12)S1B—C21B—H21A109.5
C2A—N1A—C6A122.50 (16)S1B—C21B—H21B109.5
C2A—N1A—Ni1A118.36 (13)H21A—C21B—H21B109.5
C6A—N1A—Ni1A119.14 (13)S1B—C21B—H21C109.5
C11B—N2B—C12B116.75 (11)H21A—C21B—H21C109.5
C11B—N2B—Ni1B122.56 (8)H21B—C21B—H21C109.5
C12B—N2B—Ni1B120.69 (8)S1A—C21A—H21D109.5
C12A—N2A—C11A116.53 (12)S1A—C21A—H21E109.5
C12A—N2A—Ni1A122.38 (9)H21D—C21A—H21E109.5
C11A—N2A—Ni1A121.09 (9)S1A—C21A—H21F109.5
O2A—C1A—O2Ai19.2 (7)H21D—C21A—H21F109.5
O2A—C1A—O1A126.5 (2)H21E—C21A—H21F109.5
O2Ai—C1A—O1A126.5 (2)S1A—C22A—H22A109.5
O2A—C1A—C2A117.57 (19)S1A—C22A—H22B109.5
O2Ai—C1A—C2A117.57 (19)H22A—C22A—H22B109.5
O1A—C1A—C2A114.86 (17)S1A—C22A—H22C109.5
O4B—C1B—O3B127.24 (17)H22A—C22A—H22C109.5
O4B—C1B—C2B118.13 (16)H22B—C22A—H22C109.5
O3B—C1B—C2B114.63 (15)
Symmetry codes: (i) x, y+3/2, z; (ii) x, y+1/2, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C11B—H11B···O1B0.952.503.0442 (13)117
C11B—H11B···O5A0.952.663.2871 (18)124
C11A—H11A···O3A0.952.423.0252 (14)121
C11A—H11A···O5B0.952.433.0462 (17)122
C12B—H12B···O3B0.952.372.9978 (13)123
C12A—H12A···O1A0.952.453.0221 (14)119
C12A—H12A···O1Aiii0.952.613.2230 (18)122
C21B—H21A···O2Biv0.982.493.3321 (19)144
C21A—H21D···O4Av0.982.473.277 (4)139
C21A—H21E···O2Aiii0.982.272.959 (9)126
C21A—H21E···O2Avi0.982.503.246 (9)132
C22A—H22A···O4Av0.982.573.377 (4)140
Symmetry codes: (iii) x, y+1, z; (iv) x+1, y+1/2, z; (v) x1, y+3/2, z; (vi) x, y1/2, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C11B—H11B···O1B0.952.503.0442 (13)116.8
C11B—H11B···O5A0.952.663.2871 (18)124.3
C11A—H11A···O3A0.952.423.0252 (14)121.4
C11A—H11A···O5B0.952.433.0462 (17)122.2
C12B—H12B···O3B0.952.372.9978 (13)123.1
C12A—H12A···O1A0.952.453.0221 (14)118.6
C12A—H12A···O1Ai0.952.613.2230 (18)122.3
C21B—H21A···O2Bii0.982.493.3321 (19)144.1
C21A—H21D···O4Aiii0.982.473.277 (4)139.2
C21A—H21E···O2Ai0.982.272.959 (9)126.2
C21A—H21E···O2Aiv0.982.503.246 (9)132.3
C22A—H22A···O4Aiii0.982.573.377 (4)139.5
Symmetry codes: (i) x, y+1, z; (ii) x+1, y+1/2, z; (iii) x1, y+3/2, z; (iv) x, y1/2, z.

Experimental details

Crystal data
Chemical formula[Ni(C7H3NO4)(C4H4N2)(C2H6OS)]
Mr382.03
Crystal system, space groupMonoclinic, P21/m
Temperature (K)100
a, b, c (Å)10.5631 (7), 7.0296 (4), 20.3710 (13)
β (°) 90.6447 (11)
V3)1512.54 (16)
Z4
Radiation typeMo Kα
µ (mm1)1.45
Crystal size (mm)0.37 × 0.15 × 0.05
Data collection
DiffractometerBruker APEXII DUO CCD
Absorption correctionAnalytical
based on measured indexed crystal faces; XPREP (Bruker, 2014)
Tmin, Tmax0.730, 0.965
No. of measured, independent and
observed [I > 2σ(I)] reflections
56634, 3756, 3549
Rint0.026
(sin θ/λ)max1)0.650
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.020, 0.055, 1.07
No. of reflections3756
No. of parameters256
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)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.

References

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Volume 72| Part 5| May 2016| Pages 768-771
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