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metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 70| Part 7| July 2014| Pages m265-m266
https://doi.org/10.1107/S1600536814013555

Poly[tris­­(μ-4,4′-bi­pyridine-κ2N:N′)bis­(di­methyl sulfoxide-κO)tetra­kis­(thio­cyanato-κN)dicobalt(II)]

Surasak Kaenket,a Pongthipun Phuengphai,b Chaveng Pakawatchaic and Sujittra Youngmea*

aMaterials Chemistry Research Unit, Department of Chemistry and Center of Excellence for Innovation in Chemistry, Faculty of Science, Khon Kaen University, Khon Kaen 40002, Thailand, bDepartment of Fundamental Science, Faculty of Science and Technology, Surindra Rajabhat University, Surin 32000, Thailand, and cDepartment of Chemistry, Faculty of Science, Prince of Songkla University, Hat Yai, Songkhla 90112, Thailand
*Correspondence e-mail: sujittra@kku.ac.th

(Received 27 May 2014; accepted 11 June 2014; online 18 June 2014)

The asymmetric unit of the title compound, [Co2(NCS)4(C10H8N2)3(C2H6OS)2]n, consists of one CoII atom, two thio­cyanate anions, one dimethyl sulfoxide mol­ecule and one and a half 4,4′-bi­pyridine mol­ecules. The half-molecule is completed by inversion symmetry. The CoII atom is coordin­ated in a distorted octa­hedral geometry by two N atoms from two thio­cyanate anions, one O atom from dimethyl sulfoxide as a terminal ligand and three N atoms from three 4,4′-bi­pyridine mol­ecules as bridging ligands linking the cations, with a Co⋯Co separation of 11.5964 (5) Å. This generates a two-dimensional structure parallel to (-103). A C—H⋯S hydrogen bond links the layers into a three-dimensional supra­molecular framework. The layers are stacked in an ABC fashion preventing the occurrence of inter­layer void space and hence leading to the absence of lattice solvent and/or organic guest mol­ecules in the structure.

CCDC reference: 1007744

Related literature

For related coordination polymers with ligands such as pyrazine, pyrimidine, 4,4′-bi­pyridine and SCN−, see: Wriedt & Näther (2009[Wriedt, M. & Näther, C. (2009). Dalton Trans. pp. 10192-10198.], 2010[Wriedt, M. & Näther, C. (2010). Z. Anorg. Allg. Chem. 636, 1061-1068.]); Wriedt et al. (2009[Wriedt, M., Jess, I. & Näther, C. (2009). Eur. J. Inorg. Chem. pp. 1406-1413.]); Yao & Wang (2009[Yao, R. & Wang, D. E. (2009). Acta Cryst. E65, m813.]).

[Scheme 1]

Experimental

Crystal data

  • [Co2(NCS)4(C10H8N2)3(C2H6OS)2]

  • Mr = 974.98

  • Monoclinic, P 21 /n

  • a = 11.0772 (3) Å

  • b = 16.9999 (2) Å

  • c = 11.6843 (3) Å

  • β = 103.628 (1)°

  • V = 2138.34 (8) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 1.12 mm−1

  • T = 273 K

  • 0.40 × 0.16 × 0.10 mm
Data collection

  • Bruker SMART APEX CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2000[Bruker (2000). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.591, Tmax = 0.894

  • 14262 measured reflections

  • 5584 independent reflections

  • 3936 reflections with I > 2σ(I)

  • Rint = 0.032
Refinement

  • R[F2 > 2σ(F2)] = 0.043

  • wR(F2) = 0.109

  • S = 1.01

  • 5584 reflections

  • 264 parameters

  • H-atom parameters constrained

  • Δρmax = 1.02 e Å−3

  • Δρmin = −0.58 e Å−3

Table 1
Selected bond lengths (Å)

Co1—N7 2.080 (2)
Co1—N6 2.102 (2)
Co1—O1 2.1234 (19)
Co1—N3 2.2187 (19)
Co1—N2 2.244 (2)
Co1—N1 2.2551 (19)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
C1—H1⋯S1i 0.93 2.82 3.596 (3) 141
Symmetry code: (i) [-x+{\script{3\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}].

Data collection: SMART (Bruker, 2000[Bruker (2000). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2000[Bruker (2000). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: Mercury (Macrae et al., 2008[Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.]); software used to prepare material for publication: publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).

Supporting information

CCDC reference: 1007744

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S1600536814013555/is5365sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536814013555/is5365Isup2.hkl

checkCIF report


Comment top

Metal organic frameworks can be prepared in variety methods and there are many effects influencing their structures. The solvent used in preparing is one of the most important effects on the structures. The influence of the solvent on the structure has been widely studied, for example in the study of iron(II) thiocyanato coordination polymers based on 4,4'-bipyridine using methanol as a solvent (Wriedt & Näther, 2010). This finding suggested that if more solvent and higher concentration of N-donor ligand were applied the structure is likely to involve with solvent coordination and the different metal to organic ligand ratio. The solvent has the influence on both metal to organic ligand ratio and the arrangement of the organic linker leading to the variation of the dimension and topology of the network (Yao & Wang, 2009). In addition, the type of N-donor organic linkers also affect the structure (Wriedt & Näther, 2009; Wriedt et al., 2009).

Of interest to us was this effect. A new structure with the different metal to N-donor organic ligand ratio might also be possible by alteration of the solvent, type of N-donor organic ligand, and the metal to N-donor ligand ratio in the preparation. In this contribution, we present synthesis and structural characterization of a two-dimensional framework of poly[µ-tris(4,4'-bipyridine)di(dimethyl sulfoxide)tetrathiocyanato-N-dicobalt(II)] (I)

The asymmetric unit of the title compound consists of one CoII centre, two SCN- anions, one and a half 4,4'-bpy molecules and one DMSO molecule (Fig. 1). The CoII is surrounded by two N atoms from terminal SCN- groups, one O atom from DMSO and three N atoms from three 4,4'-bpy (Table 1). The 4,4'-bpy acts as a bridge linking metal centres and generates a two-dimensional structure with rectangular spaces (11.60 x 23.25 Å) within layer (Fig. 2). Due to the arrangement of the linker and metal to N-donor organic ligand ratio of 1:1.5, the space within the layer is twice as compared to the related two-dimensional compound {[Fe(4,4'-bpy)2(SCN)2](MeOH)2}n (Wriedt & Näther, 2010). The layers are stacked in an ABC fashion (Fig. 3). The plane parallel to the layer is (103). The metal atoms in one layer sit above or below the rectangular spaces. As a result, the terminal SCN- and DMSO ligands arrange approximately perpendicular to the layer plane and fill up the spaces between adjacent layers. This arrangement of the layers is in the ABC fashion preventing the occurrence of the interlayer spaces along the crystallographic c axis and hence leading to the absence of lattice solvent and/or organic guest molecules in the interlayer spaces (Fig. 3). In addition, the extended structure of I has been illustrated (Fig. 4). The hydrogen bonds between H1 and S1 link the layers with the distance of 2.82 Å (Table 2). As a result, these layers are assembled into a three-dimensional supramolecular framework.

Related literature top

For related coordination polymers with ligands such as pyrazine, pyrimidine, 4,4'-bipyridine and SCN-, see: Wriedt & Näther (2009, 2010); Wriedt et al. (2009); Yao & Wang (2009).

Experimental top

Compound I was synthesized by direct method in a molar ratio of 1:3:1 of Co(NO3)2·6H2O, 4,4'-bpy and KSCN, respectively. To prepare the reaction mixture, Co(NO3)2·6H2O (0.5 mmol, 0.15 g) and KSCN (0.5 mmol, 0.05 g) were dissolved in water (10 mL). Then 10 ml of ethanoic solution of 4,4'-bpy (1.5 mmol, 0.23 g) was added. The mixture was stirred, then 10 mL of DMSO and 0.5 mL of 6 M HNO3 was slowly added to assist dissolution.The mixture was then heated at 60 °C for 15 mins. It was set at room temperature for a slow evaporation. After 15 days, pink crystals were obtained.

Refinement top

C-bound H atoms were positioned geometrically, with C—H = 0.93 (aromatic) or 0.96 Å (methyl), and included as riding atoms, with Uiso(H) = 1.5Ueq (C) for methyl groups and 1.2Ueq(C) otherwise.

Structure description top

Metal organic frameworks can be prepared in variety methods and there are many effects influencing their structures. The solvent used in preparing is one of the most important effects on the structures. The influence of the solvent on the structure has been widely studied, for example in the study of iron(II) thiocyanato coordination polymers based on 4,4'-bipyridine using methanol as a solvent (Wriedt & Näther, 2010). This finding suggested that if more solvent and higher concentration of N-donor ligand were applied the structure is likely to involve with solvent coordination and the different metal to organic ligand ratio. The solvent has the influence on both metal to organic ligand ratio and the arrangement of the organic linker leading to the variation of the dimension and topology of the network (Yao & Wang, 2009). In addition, the type of N-donor organic linkers also affect the structure (Wriedt & Näther, 2009; Wriedt et al., 2009).

Of interest to us was this effect. A new structure with the different metal to N-donor organic ligand ratio might also be possible by alteration of the solvent, type of N-donor organic ligand, and the metal to N-donor ligand ratio in the preparation. In this contribution, we present synthesis and structural characterization of a two-dimensional framework of poly[µ-tris(4,4'-bipyridine)di(dimethyl sulfoxide)tetrathiocyanato-N-dicobalt(II)] (I)

The asymmetric unit of the title compound consists of one CoII centre, two SCN- anions, one and a half 4,4'-bpy molecules and one DMSO molecule (Fig. 1). The CoII is surrounded by two N atoms from terminal SCN- groups, one O atom from DMSO and three N atoms from three 4,4'-bpy (Table 1). The 4,4'-bpy acts as a bridge linking metal centres and generates a two-dimensional structure with rectangular spaces (11.60 x 23.25 Å) within layer (Fig. 2). Due to the arrangement of the linker and metal to N-donor organic ligand ratio of 1:1.5, the space within the layer is twice as compared to the related two-dimensional compound {[Fe(4,4'-bpy)2(SCN)2](MeOH)2}n (Wriedt & Näther, 2010). The layers are stacked in an ABC fashion (Fig. 3). The plane parallel to the layer is (103). The metal atoms in one layer sit above or below the rectangular spaces. As a result, the terminal SCN- and DMSO ligands arrange approximately perpendicular to the layer plane and fill up the spaces between adjacent layers. This arrangement of the layers is in the ABC fashion preventing the occurrence of the interlayer spaces along the crystallographic c axis and hence leading to the absence of lattice solvent and/or organic guest molecules in the interlayer spaces (Fig. 3). In addition, the extended structure of I has been illustrated (Fig. 4). The hydrogen bonds between H1 and S1 link the layers with the distance of 2.82 Å (Table 2). As a result, these layers are assembled into a three-dimensional supramolecular framework.

For related coordination polymers with ligands such as pyrazine, pyrimidine, 4,4'-bipyridine and SCN-, see: Wriedt & Näther (2009, 2010); Wriedt et al. (2009); Yao & Wang (2009).

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: Mercury (Macrae et al., 2008); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top
[Figure 1] Fig. 1. A view of the local coordination of the CoII in the title compound, showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. Hydrogen atoms are omitted for clarity.
[Figure 2] Fig. 2. A partial packing diagram of the title compound, showing the two-dimensional structure via 4,4'-bpy bridges generating rectangular spaces.
[Figure 3] Fig. 3. A partial packing diagram of the title compound, showing that terminal ligands, DMSO and SCN- fill up the rectangular space of adjacent layer (a) and ABC arrangement structure layers prevent the occurrence of the channel along C axis (b).
[Figure 4] Fig. 4. The extended structure of the title compound illustrates the hydrogen bonds (dotted lines) between H1 and S1 (-x + 3/2, y - 1/2, -z + 1/2) linking two-dimensional layers leading to a three-dimensional supramolecular framework. The adjacent layers are shown in different colours.
Poly[tris(µ-4,4'-bipyridine-κ2N:N')bis(dimethyl sulfoxide-κO)tetrakis(thiocyanato-κN)dicobalt(II)] top
Crystal data top
[Co2(NCS)4(C10H8N2)3(C2H6OS)2]Z = 2
Mr = 974.98F(000) = 1000
Monoclinic, P21/nDx = 1.514 Mg m−3
Hall symbol: -P 2ynMo Kα radiation, λ = 0.71073 Å
a = 11.0772 (3) ŵ = 1.12 mm−1
b = 16.9999 (2) ÅT = 273 K
c = 11.6843 (3) ÅBlock, pink
β = 103.628 (1)°0.40 × 0.16 × 0.10 mm
V = 2138.34 (8) Å3
Data collection top
Bruker SMART APEX CCD
diffractometer		5584 independent reflections
Radiation source: fine-focus sealed tube3936 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.032
phi and ω scansθmax = 29.8°, θmin = 2.2°
Absorption correction: multi-scan
(SADABS; Bruker, 2000)		h = −14→14
Tmin = 0.591, Tmax = 0.894k = −16→22
14262 measured reflectionsl = −12→15
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)] = 0.043Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.109H-atom parameters constrained
S = 1.01 w = 1/[σ2(Fo2) + (0.0522P)2 + 1.1491P]
where P = (Fo2 + 2Fc2)/3
5584 reflections(Δ/σ)max < 0.001
264 parametersΔρmax = 1.02 e Å−3
0 restraintsΔρmin = −0.58 e Å−3
Crystal data top
[Co2(NCS)4(C10H8N2)3(C2H6OS)2]V = 2138.34 (8) Å3
Mr = 974.98Z = 2
Monoclinic, P21/nMo Kα radiation
a = 11.0772 (3) ŵ = 1.12 mm−1
b = 16.9999 (2) ÅT = 273 K
c = 11.6843 (3) Å0.40 × 0.16 × 0.10 mm
β = 103.628 (1)°
Data collection top
Bruker SMART APEX CCD
diffractometer		5584 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2000)		3936 reflections with I > 2σ(I)
Tmin = 0.591, Tmax = 0.894Rint = 0.032
14262 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0430 restraints
wR(F2) = 0.109H-atom parameters constrained
S = 1.01Δρmax = 1.02 e Å−3
5584 reflectionsΔρmin = −0.58 e Å−3
264 parameters
Special details top

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

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Co10.61610 (3)0.238576 (18)0.34507 (3)0.02619 (10)
S30.74846 (7)0.21001 (5)0.14197 (7)0.04276 (18)
S20.57089 (8)0.31500 (5)0.72918 (8)0.0535 (2)
S10.93773 (9)0.42788 (7)0.32672 (16)0.1102 (6)
N30.47394 (17)0.14430 (11)0.30393 (18)0.0268 (4)
N20.47009 (19)0.33263 (12)0.30583 (19)0.0309 (5)
N10.76429 (18)0.14581 (12)0.39797 (18)0.0303 (4)
O10.62030 (17)0.22923 (12)0.16482 (17)0.0396 (4)
N70.6038 (2)0.25004 (14)0.5192 (2)0.0394 (5)
C150.4133 (2)0.12562 (14)0.1932 (2)0.0297 (5)
H150.43150.15410.13140.036*
N60.7569 (2)0.32360 (14)0.3613 (2)0.0435 (6)
C80.2944 (2)0.45622 (14)0.2665 (2)0.0299 (5)
C30.9512 (2)0.03082 (14)0.4782 (2)0.0279 (5)
C160.5904 (2)0.27781 (15)0.6063 (2)0.0324 (6)
C50.8725 (2)0.16319 (15)0.4734 (2)0.0366 (6)
H50.88560.21490.49920.044*
C90.2624 (2)0.38055 (16)0.2287 (3)0.0404 (7)
H90.18130.36920.18880.048*
C20.8399 (2)0.01292 (15)0.3977 (3)0.0398 (7)
H20.8257−0.03790.36810.048*
C110.4472 (2)0.10091 (15)0.3912 (2)0.0321 (5)
H110.48740.11280.46850.039*
C100.3514 (2)0.32131 (15)0.2502 (3)0.0395 (6)
H100.32680.27080.22420.047*
C40.9657 (2)0.10903 (15)0.5153 (2)0.0376 (6)
H41.03820.12480.56820.045*
C10.7503 (2)0.07089 (15)0.3616 (3)0.0373 (6)
H10.67650.05680.30920.045*
C60.5003 (3)0.40610 (16)0.3448 (3)0.0447 (7)
H60.58170.41570.38550.054*
C170.8323 (3)0.36663 (17)0.3468 (3)0.0437 (7)
C140.3251 (2)0.06625 (15)0.1664 (2)0.0319 (5)
H140.28420.05670.08860.038*
C70.4169 (3)0.46839 (16)0.3280 (3)0.0469 (8)
H70.44270.51800.35760.056*
C190.7763 (4)0.2828 (3)0.0436 (4)0.0746 (12)
H19A0.70510.2873−0.02140.112*
H19B0.84760.26840.01480.112*
H19C0.79140.33240.08380.112*
C180.7228 (5)0.1284 (3)0.0458 (5)0.0992 (17)
H18A0.69430.08460.08420.149*
H18B0.79890.11460.02500.149*
H18C0.66110.1416−0.02410.149*
C120.3626 (2)0.03931 (15)0.3716 (2)0.0344 (6)
H120.34870.01020.43470.041*
C130.2983 (2)0.02117 (14)0.2567 (2)0.0298 (5)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Co10.02248 (16)0.02112 (16)0.03429 (18)0.00099 (12)0.00529 (12)0.00138 (13)
S30.0366 (4)0.0522 (4)0.0425 (4)0.0033 (3)0.0155 (3)0.0038 (3)
S20.0528 (5)0.0601 (5)0.0505 (5)−0.0048 (4)0.0179 (4)−0.0164 (4)
S10.0445 (5)0.0713 (7)0.1993 (16)−0.0200 (5)−0.0023 (7)0.0688 (9)
N30.0229 (9)0.0205 (10)0.0362 (11)0.0000 (7)0.0053 (8)0.0014 (8)
N20.0276 (10)0.0266 (11)0.0374 (12)0.0033 (8)0.0055 (9)−0.0002 (9)
N10.0289 (10)0.0263 (10)0.0344 (11)0.0059 (8)0.0049 (8)0.0017 (9)
O10.0297 (9)0.0504 (12)0.0399 (10)−0.0013 (8)0.0105 (8)0.0048 (9)
N70.0391 (12)0.0393 (13)0.0380 (12)0.0040 (10)0.0054 (10)0.0015 (10)
C150.0293 (12)0.0246 (12)0.0353 (13)−0.0024 (9)0.0075 (10)0.0040 (10)
N60.0340 (12)0.0319 (12)0.0631 (16)−0.0024 (10)0.0083 (11)−0.0004 (11)
C80.0277 (12)0.0257 (12)0.0364 (13)0.0050 (9)0.0079 (10)0.0004 (10)
C30.0249 (11)0.0260 (12)0.0325 (12)0.0051 (9)0.0061 (9)0.0009 (10)
C160.0292 (12)0.0264 (13)0.0394 (14)−0.0001 (9)0.0035 (10)0.0015 (10)
C50.0342 (13)0.0252 (12)0.0450 (15)0.0050 (10)−0.0017 (11)−0.0053 (11)
C90.0274 (13)0.0291 (13)0.0589 (18)0.0036 (10)−0.0012 (12)−0.0063 (12)
C20.0325 (13)0.0233 (12)0.0560 (17)0.0040 (10)−0.0048 (12)−0.0074 (12)
C110.0326 (13)0.0286 (13)0.0339 (13)−0.0028 (10)0.0053 (10)0.0004 (10)
C100.0334 (13)0.0227 (12)0.0579 (18)0.0029 (10)0.0018 (12)−0.0071 (12)
C40.0316 (13)0.0296 (14)0.0452 (15)0.0038 (10)−0.0037 (11)−0.0054 (11)
C10.0263 (12)0.0303 (13)0.0491 (16)0.0044 (10)−0.0032 (11)−0.0042 (12)
C60.0273 (13)0.0306 (14)0.069 (2)0.0041 (10)−0.0027 (13)−0.0075 (13)
C170.0301 (13)0.0312 (14)0.0650 (19)0.0001 (11)0.0015 (13)0.0108 (13)
C140.0309 (12)0.0299 (13)0.0326 (13)−0.0054 (10)0.0029 (10)0.0001 (10)
C70.0348 (14)0.0253 (13)0.073 (2)0.0028 (11)−0.0029 (14)−0.0119 (13)
C190.063 (2)0.088 (3)0.086 (3)0.014 (2)0.044 (2)0.039 (2)
C180.111 (4)0.095 (4)0.109 (4)−0.019 (3)0.059 (3)−0.054 (3)
C120.0374 (14)0.0312 (13)0.0352 (14)−0.0073 (11)0.0097 (11)0.0056 (11)
C130.0259 (12)0.0223 (12)0.0411 (14)−0.0025 (9)0.0076 (10)0.0002 (10)
Geometric parameters (Å, º) top
Co1—N72.080 (2)C3—C3ii1.506 (4)
Co1—N62.102 (2)C5—C41.384 (3)
Co1—O12.1234 (19)C5—H50.9300
Co1—N32.2187 (19)C9—C101.390 (4)
Co1—N22.244 (2)C9—H90.9300
Co1—N12.2551 (19)C2—C11.392 (3)
S3—O11.5401 (19)C2—H20.9300
S3—C191.765 (4)C11—C121.388 (3)
S3—C181.766 (4)C11—H110.9300
S2—C161.629 (3)C10—H100.9300
S1—C171.623 (3)C4—H40.9300
N3—C111.347 (3)C1—H10.9300
N3—C151.348 (3)C6—C71.388 (4)
N2—C101.336 (3)C6—H60.9300
N2—C61.344 (3)C14—C131.391 (4)
N1—C11.340 (3)C14—H140.9300
N1—C51.343 (3)C7—H70.9300
N7—C161.163 (4)C19—H19A0.9600
C15—C141.388 (3)C19—H19B0.9600
C15—H150.9300C19—H19C0.9600
N6—C171.152 (4)C18—H18A0.9600
C8—C91.379 (4)C18—H18B0.9600
C8—C71.393 (4)C18—H18C0.9600
C8—C13i1.489 (3)C12—C131.398 (4)
C3—C41.396 (3)C12—H120.9300
C3—C21.396 (3)C13—C8iii1.489 (3)
N7—Co1—N693.76 (10)C10—C9—H9120.0
N7—Co1—O1177.34 (8)C1—C2—C3120.2 (2)
N6—Co1—O187.22 (9)C1—C2—H2119.9
N7—Co1—N394.19 (9)C3—C2—H2119.9
N6—Co1—N3171.85 (9)N3—C11—C12123.3 (2)
O1—Co1—N384.91 (7)N3—C11—H11118.4
N7—Co1—N285.58 (8)C12—C11—H11118.4
N6—Co1—N290.69 (8)N2—C10—C9123.9 (2)
O1—Co1—N291.94 (8)N2—C10—H10118.0
N3—Co1—N291.71 (7)C9—C10—H10118.0
N7—Co1—N190.49 (8)C5—C4—C3120.1 (2)
N6—Co1—N188.83 (8)C5—C4—H4119.9
O1—Co1—N192.00 (8)C3—C4—H4119.9
N3—Co1—N189.30 (7)N1—C1—C2123.8 (2)
N2—Co1—N1176.00 (8)N1—C1—H1118.1
O1—S3—C19105.89 (15)C2—C1—H1118.1
O1—S3—C18105.07 (18)N2—C6—C7123.8 (2)
C19—S3—C1899.4 (3)N2—C6—H6118.1
C11—N3—C15116.7 (2)C7—C6—H6118.1
C11—N3—Co1120.20 (16)N6—C17—S1179.5 (3)
C15—N3—Co1123.09 (16)C15—C14—C13119.6 (2)
C10—N2—C6115.9 (2)C15—C14—H14120.2
C10—N2—Co1125.18 (17)C13—C14—H14120.2
C6—N2—Co1118.89 (17)C6—C7—C8119.6 (2)
C1—N1—C5115.8 (2)C6—C7—H7120.2
C1—N1—Co1123.75 (16)C8—C7—H7120.2
C5—N1—Co1120.37 (16)S3—C19—H19A109.5
S3—O1—Co1115.11 (11)S3—C19—H19B109.5
C16—N7—Co1161.0 (2)H19A—C19—H19B109.5
N3—C15—C14123.6 (2)S3—C19—H19C109.5
N3—C15—H15118.2H19A—C19—H19C109.5
C14—C15—H15118.2H19B—C19—H19C109.5
C17—N6—Co1166.3 (3)S3—C18—H18A109.5
C9—C8—C7116.7 (2)S3—C18—H18B109.5
C9—C8—C13i121.3 (2)H18A—C18—H18B109.5
C7—C8—C13i122.0 (2)S3—C18—H18C109.5
C4—C3—C2115.8 (2)H18A—C18—H18C109.5
C4—C3—C3ii122.5 (3)H18B—C18—H18C109.5
C2—C3—C3ii121.7 (3)C11—C12—C13119.8 (2)
N7—C16—S2178.9 (3)C11—C12—H12120.1
N1—C5—C4124.2 (2)C13—C12—H12120.1
N1—C5—H5117.9C14—C13—C12117.1 (2)
C4—C5—H5117.9C14—C13—C8iii122.2 (2)
C8—C9—C10120.0 (2)C12—C13—C8iii120.8 (2)
C8—C9—H9120.0
N7—Co1—N3—C11−21.36 (19)N3—Co1—N7—C16−124.4 (7)
N6—Co1—N3—C11145.8 (5)N2—Co1—N7—C16−33.0 (7)
O1—Co1—N3—C11161.15 (19)N1—Co1—N7—C16146.2 (7)
N2—Co1—N3—C11−107.05 (18)C11—N3—C15—C141.3 (4)
N1—Co1—N3—C1169.08 (18)Co1—N3—C15—C14179.32 (19)
N7—Co1—N3—C15160.68 (19)N7—Co1—N6—C17180.0 (10)
N6—Co1—N3—C15−32.1 (7)O1—Co1—N6—C17−2.5 (10)
O1—Co1—N3—C15−16.81 (19)N3—Co1—N6—C1712.8 (14)
N2—Co1—N3—C1574.99 (19)N2—Co1—N6—C17−94.4 (10)
N1—Co1—N3—C15−108.88 (19)N1—Co1—N6—C1789.5 (10)
N7—Co1—N2—C10−107.9 (2)C1—N1—C5—C4−1.1 (4)
N6—Co1—N2—C10158.4 (2)Co1—N1—C5—C4176.5 (2)
O1—Co1—N2—C1071.1 (2)C7—C8—C9—C10−1.5 (4)
N3—Co1—N2—C10−13.8 (2)C13i—C8—C9—C10179.1 (3)
N1—Co1—N2—C10−118.5 (11)C4—C3—C2—C1−1.7 (4)
N7—Co1—N2—C669.0 (2)C3ii—C3—C2—C1178.4 (3)
N6—Co1—N2—C6−24.8 (2)C15—N3—C11—C120.4 (4)
O1—Co1—N2—C6−112.0 (2)Co1—N3—C11—C12−177.7 (2)
N3—Co1—N2—C6163.0 (2)C6—N2—C10—C92.0 (4)
N1—Co1—N2—C658.4 (12)Co1—N2—C10—C9178.9 (2)
N7—Co1—N1—C1116.1 (2)C8—C9—C10—N2−0.6 (5)
N6—Co1—N1—C1−150.2 (2)N1—C5—C4—C30.7 (5)
O1—Co1—N1—C1−63.0 (2)C2—C3—C4—C50.7 (4)
N3—Co1—N1—C121.9 (2)C3ii—C3—C4—C5−179.4 (3)
N2—Co1—N1—C1126.6 (11)C5—N1—C1—C20.1 (4)
N7—Co1—N1—C5−61.4 (2)Co1—N1—C1—C2−177.5 (2)
N6—Co1—N1—C532.4 (2)C3—C2—C1—N11.4 (5)
O1—Co1—N1—C5119.5 (2)C10—N2—C6—C7−1.4 (5)
N3—Co1—N1—C5−155.6 (2)Co1—N2—C6—C7−178.5 (3)
N2—Co1—N1—C5−50.8 (12)N3—C15—C14—C13−1.8 (4)
C19—S3—O1—Co1−127.1 (2)N2—C6—C7—C8−0.6 (5)
C18—S3—O1—Co1128.3 (2)C9—C8—C7—C62.0 (5)
N7—Co1—O1—S3167.2 (18)C13i—C8—C7—C6−178.6 (3)
N6—Co1—O1—S355.48 (13)N3—C11—C12—C13−1.6 (4)
N3—Co1—O1—S3−122.38 (13)C15—C14—C13—C120.5 (4)
N2—Co1—O1—S3146.08 (13)C15—C14—C13—C8iii−179.4 (2)
N1—Co1—O1—S3−33.25 (13)C11—C12—C13—C141.1 (4)
N6—Co1—N7—C1657.4 (7)C11—C12—C13—C8iii−179.0 (2)
O1—Co1—N7—C16−54 (2)
Symmetry codes: (i) −x+1/2, y+1/2, −z+1/2; (ii) −x+2, −y, −z+1; (iii) −x+1/2, y−1/2, −z+1/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C1—H1···S1iv0.932.823.596 (3)141
Symmetry code: (iv) −x+3/2, y−1/2, −z+1/2.
Selected bond lengths (Å) top
Co1—N72.080 (2)Co1—N32.2187 (19)
Co1—N62.102 (2)Co1—N22.244 (2)
Co1—O12.1234 (19)Co1—N12.2551 (19)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C1—H1···S1i0.932.823.596 (3)141
Symmetry code: (i) −x+3/2, y−1/2, −z+1/2.
 

Acknowledgements

The authors gratefully acknowledge The Thailand Research Fund (BRG5680009), the Higher Education Research Promotion and National Research University Project of Thailand, through the Advanced Functional Materials Cluster of Khon Kaen University, and the Center of Excellence for Innovation in Chemistry (PERCH–CIC), Office of the Higher Education Commission, Ministry of Education, Thailand, for financial support.

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ISSN: 2056-9890
Volume 70| Part 7| July 2014| Pages m265-m266
https://doi.org/10.1107/S1600536814013555
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