Crystal structure of bis­(aceto­nitrile-κN)bis­(4-benzoyl­pyridine-κN)bis­(thio­cyanato-κN)cobalt(II)

Suckert, S.; Werner, J.; Jess, I.; Näther, C.

doi:10.1107/S2056989017002201

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Volume 73| Part 3| March 2017| Pages 365-368

https://doi.org/10.1107/S2056989017002201

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Crystal structure of bis(acetonitrile-κN)bis(4-benzoylpyridine-κN)bis(thiocyanato-κN)cobalt(II)

Stefan Suckert,^a ^* Julia Werner,^a Inke Jess ^a and Christian Näther ^a

^aInstitut für Anorganische Chemie, Christian-Albrechts-Universität Kiel, Max-Eyth Strasse 2, D-24118 Kiel, Germany
^*Correspondence e-mail: ssuckert@ac.uni-kiel.de

Edited by M. Weil, Vienna University of Technology, Austria (Received 30 January 2017; accepted 9 February 2017; online 14 February 2017)

The crystal structure of the title compound, [Co(NCS)₂(C₂H₃N)₂(C₁₂H₉NO)₂], consists of cobalt(II) cations that are octahedrally coordinated by the N atoms of two terminal thiocyanate anions, two acetonitrile molecules and two 4-benzoylpyridine ligands. The discrete complexes are located on centres of inversion. They are connected by weak intermolecular C—H⋯O and C—H⋯S hydrogen-bonding interactions between one of the pyridine H atoms and the carbonyl O atom, and between one of the methyl H atoms of the acetonitrile molecule and the thiocyanate S atoms into layers parallel to (101). No pronounced intermolecular interactions are observed between these layers.

Keywords: crystal structure; discrete complex; cobalt(II) thiocyanate; 4-benzoylpyridine; hydrogen bonding.

CCDC reference: 1532114

1. Chemical context

In recent times, the synthesis of materials exhibiting cooperative magnetic properties has still been a topic of major interest in coordination chemistry (Zhang et al., 2011 ). A good approach for the preparation of such compounds is the use of small anionic ligands such as e.g. thiocyanate anions to link paramagnetic cations, enabling a magnetic exchange between the cations (Palion-Gazda et al., 2015 ; Massoud et al., 2013 ). During the last few years, our group has reported on a number of coordination polymers with thiocyanato ligands that show different magnetic phenomena, including a slow relaxation of the magnetization (Werner et al., 2014 , 2015a ,b ,c ,d ). In the course of this project, we became interested in compounds based on 4-benzoylpyridine, for which at that time only three thiocyanato compounds had been reported (Drew et al., 1985 ; Soliman et al., 2014 ; Bai et al., 2011 ). During these investigations, we obtained a compound with composition [Co(NCS)₂(4-benzoylpyridine)₂] in which the Co^II cations are linked by pairs of anionic ligands into chains. In contrast to all other such chain compounds where all ligands are always trans-coordinating, in this compound a cis-coordination of the N and the S atoms of the thiocyanate anions was observed (Rams et al., 2017 ). Therefore, we assumed that this compound might be metastable and that a second modification with the usual trans-coordination could be prepared by thermal annealing of precursors with terminal N-bonded thiocyanate anions. In this context, it is noted that there are many examples where different modifications or isomers have been obtained by this alternative route (Werner et al., 2015a,c; Suckert et al., 2016 ). In the course of these studies, crystals of the title compound, [Co(NCS)₂(C₂H₃N)₂(C₁₂H₉NO)₂], were obtained and characterized by single crystal X-ray diffraction. Unfortunately, no pure crystalline powder could be obtained, which prevented further investigations of the thermal properties of this compound.

2. Structural commentary

The asymmetric unit of the title compound consists of one cobalt(II) cation, one thiocyanato anion, one acetonitrile molecule and one neutral 4-benzoylpyridine ligand. The cobalt(II) cation is located on a center of inversion while the thiocyanato anion, the acetonitrile molecule and the 4-benzoylpyridine ligand are located in general positions. The Co^II cation is octahedrally coordinated by the N atoms of two terminal anionic ligands, two acetonitrile molecules and two 4-benzoylpyridine ligands (Fig. 1). As expected, the Co—N bond lengths to the thiocyanate anions are significantly shorter [2.0520 (15) Å] than those to the pyridine N atom of the neutral 4-benzoylpyridine ligand [2.1831 (13) Å]. All bond lengths are in agreement with values reported in the literature (Drew et al., 1985; Soliman et al., 2014). The 4-benzoylpyridine ligand is not planar; the dihedral angle between the phenyl and pyridine rings is 55.37 (8)°. This is in agreement with values retrieved from the literature, which vary between 40.4 and 74.3° (Escuer et al., 2000 , 2004 ).

Figure 1
View of a discrete complex of the title compound, showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 50% probability level. [Symmetry code: (i) −x + 1, −y, −z + 1.]

3. Supramolecular features

In the crystal structure of the title compound, the discrete complexes are linked by intermolecular C—H⋯O hydrogen bonds between one of the pyridine ring H atoms and the oxygen atom of the 4-benzoylpyridine ligand of a neighboring complex into dimers, which are further connected into chains (Fig. 2, Table 1). These chains are further linked into layers parallel to (101) by centrosymmetric pairs of intermolecular C—H⋯S hydrogen bonds between one of the acetonitrile hydrogen atoms and the neighbouring thiocyanato S atom (Fig. 3, Table 1). Pronounced intermolecular interactions are not observed between these layers.

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3A⋯S1ⁱ	0.98	2.85	3.771 (3)	156
C11—H11⋯O11ⁱⁱ	0.95	2.49	3.193 (2)	131
Symmetry codes: (i) x, y-1, z; (ii) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

Figure 2
View of the hydrogen-bonded layers extending parallel to (101). Hydrogen bonds are shown as dashed lines.

Figure 3
Part of the crystal structure of the title compound, showing the hydrogen-bonded layers. Hydrogen bonds are shown as dashed lines.

4. Database survey

To the best of our knowledge, there are only three coordination compounds with thiocyanato ligands and with 4-benzoylpyridine reported in the Cambridge Structural Database (Version 5.38, last update 2016; Groom et al., 2016 ). In two of these structures, Co^II or Ni^II cations are octahedrally coordinated by four 4-benzoylpyridine ligands and two thiocyanate anions (Drew et al., 1985; Soliman et al., 2014). In the third compound, Cu^II cations are coordinated in a square-planar mode by two 4-benzoylpyridine ligands and two thiocyanate anions (Bai et al., 2011). A general search for coordination compounds with 4-benzoylpyridine resulted in 22 structures including the aforementioned ones. One of these compounds consists of Mn^II cations that are octahedrally coordinated by two 4-benzoylpyridine ligands as well as by four μ_1,3-bridging azido ligands and linked into chains by the anionic ligands (Mautner et al., 2015 ).

5. Synthesis and crystallization

Co(NCS)₂ and 4-benzoylpyridine were purchased from Alfa Aesar. Crystals of the title compound suitable for single crystal X-ray diffraction were obtained by the reaction of 26.3 mg Co(NCS)₂ (0.15 mmol) with 55.0 mg 4-benzoylpyridine (0.3 mmol) in acetonitrile (1.5 ml) after a few days.

6. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2. The C-bound H atoms were positioned with idealized geometry and were refined with fixed isotropic displacement parameters U_iso(H) = 1.2U_eq(C) for aromatic and U_iso(H) = 1.5 U_eq(C) for methyl H atoms using a riding model. The methyl H atoms were allowed to rotate but not to tip.

Table 2
Experimental details

Crystal data
Chemical formula	[Co(NCS)₂(C₂H₃N)₂(C₁₂H₉NO)₂]
M_r	623.60
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	200
a, b, c (Å)	10.0304 (6), 8.3355 (4), 18.2581 (12)
β (°)	90.547 (8)
V (Å³)	1526.46 (15)
Z	2
Radiation type	Mo Kα
μ (mm⁻¹)	0.74
Crystal size (mm)	0.16 × 0.08 × 0.02

Data collection
Diffractometer	Stoe IPDS1
Absorption correction	Numerical (X-SHAPE and X-RED32; Stoe, 2008 )
T_min, T_max	0.897, 0.964
No. of measured, independent and observed [I > 2σ(I)] reflections	17991, 3347, 2895
R_int	0.032
(sin θ/λ)_max (Å⁻¹)	0.640

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.036, 0.096, 1.04
No. of reflections	3347
No. of parameters	189
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.46, −0.69
Computer programs: X-AREA (Stoe, 2008), SHELXS97 (Sheldrick, 2008 ), SHELXL2014 (Sheldrick, 2015 ), XP in SHELXTL (Sheldrick, 2008), DIAMOND (Brandenburg, 1999 ) and publCIF (Westrip, 2010 ).

Supporting information

CCDC reference: 1532114

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2056989017002201/wm5365sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989017002201/wm5365Isup2.hkl

checkCIF report

Computing details top

Data collection: X-AREA (Stoe, 2008); cell refinement: X-AREA (Stoe, 2008); data reduction: X-AREA (Stoe, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: XP in SHELXTL (Sheldrick, 2008) and DIAMOND (Brandenburg, 1999); software used to prepare material for publication: publCIF (Westrip, 2010).

Bis(acetonitrile-κN)bis(4-benzoylpyridine-κN)bis(thiocyanato-κN)cobalt(II) top

Crystal data top

[Co(NCS)₂(C₂H₃N)₂(C₁₂H₉NO)₂]	F(000) = 642
M_r = 623.60	D_x = 1.357 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
a = 10.0304 (6) Å	Cell parameters from 17991 reflections
b = 8.3355 (4) Å	θ = 2.7–27.1°
c = 18.2581 (12) Å	µ = 0.74 mm⁻¹
β = 90.547 (8)°	T = 200 K
V = 1526.46 (15) Å³	Block, purple
Z = 2	0.16 × 0.08 × 0.02 mm

Data collection top

Stoe IPDS-1 diffractometer	2895 reflections with I > 2σ(I)
phi scans	R_int = 0.032
Absorption correction: numerical (X-SHAPE and X-RED32; Stoe, 2008)	θ_max = 27.1°, θ_min = 2.7°
T_min = 0.897, T_max = 0.964	h = −12→12
17991 measured reflections	k = −10→10
3347 independent reflections	l = −23→23

Refinement top

Refinement on F²	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.036	w = 1/[σ²(F_o²) + (0.0604P)² + 0.5217P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.096	(Δ/σ)_max < 0.001
S = 1.04	Δρ_max = 0.46 e Å⁻³
3347 reflections	Δρ_min = −0.69 e Å⁻³
189 parameters	Extinction correction: SHELXL2014 (Sheldrick, 2015), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.030 (3)

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

	x	y	z	U_iso*/U_eq
Co1	0.5000	0.0000	0.5000	0.02109 (12)
N1	0.65155 (15)	0.11822 (18)	0.55359 (9)	0.0322 (3)
C1	0.71187 (17)	0.2142 (2)	0.58531 (10)	0.0313 (4)
S1	0.79948 (6)	0.34828 (9)	0.62877 (5)	0.0698 (3)
N2	0.49639 (16)	−0.17253 (18)	0.58858 (8)	0.0311 (3)
C2	0.50846 (19)	−0.2619 (2)	0.63506 (10)	0.0317 (4)
C3	0.5267 (3)	−0.3769 (3)	0.69412 (13)	0.0514 (6)
H3A	0.5739	−0.4714	0.6757	0.077*
H3B	0.4395	−0.4093	0.7128	0.077*
H3C	0.5791	−0.3276	0.7337	0.077*
N11	0.35979 (14)	0.15671 (16)	0.55624 (7)	0.0234 (3)
C11	0.37171 (18)	0.1751 (2)	0.62899 (9)	0.0281 (4)
H11	0.4386	0.1159	0.6543	0.034*
C12	0.29053 (18)	0.2770 (2)	0.66876 (9)	0.0283 (4)
H12	0.3009	0.2853	0.7204	0.034*
C13	0.19360 (17)	0.36697 (18)	0.63229 (9)	0.0240 (3)
C14	0.18049 (17)	0.3477 (2)	0.55676 (9)	0.0266 (3)
H14	0.1153	0.4065	0.5299	0.032*
C15	0.26444 (17)	0.2409 (2)	0.52146 (9)	0.0262 (3)
H15	0.2538	0.2267	0.4701	0.031*
C16	0.10657 (17)	0.4749 (2)	0.67758 (9)	0.0253 (3)
C17	0.06203 (16)	0.63359 (18)	0.64974 (9)	0.0238 (3)
C18	0.13193 (17)	0.7173 (2)	0.59627 (10)	0.0296 (4)
H18	0.2059	0.6687	0.5729	0.036*
C19	0.0930 (2)	0.8723 (2)	0.57732 (12)	0.0390 (4)
H19	0.1417	0.9300	0.5416	0.047*
C20	−0.0159 (2)	0.9428 (2)	0.61001 (12)	0.0396 (5)
H20	−0.0419	1.0484	0.5966	0.048*
C21	−0.08743 (19)	0.8590 (2)	0.66259 (11)	0.0361 (4)
H21	−0.1631	0.9070	0.6845	0.043*
C22	−0.04865 (17)	0.7059 (2)	0.68300 (10)	0.0293 (4)
H22	−0.0968	0.6497	0.7195	0.035*
O11	0.07747 (15)	0.43077 (16)	0.73898 (7)	0.0373 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Co1	0.02286 (18)	0.01851 (17)	0.02185 (17)	0.00227 (11)	−0.00268 (11)	−0.00305 (10)
N1	0.0281 (7)	0.0316 (8)	0.0370 (8)	−0.0008 (6)	−0.0050 (6)	−0.0088 (6)
C1	0.0233 (8)	0.0312 (9)	0.0393 (9)	0.0064 (7)	−0.0022 (7)	−0.0102 (7)
S1	0.0407 (3)	0.0604 (4)	0.1081 (6)	−0.0008 (3)	−0.0150 (3)	−0.0554 (4)
N2	0.0377 (8)	0.0274 (7)	0.0281 (7)	0.0052 (6)	0.0022 (6)	0.0011 (6)
C2	0.0358 (9)	0.0264 (8)	0.0330 (9)	0.0051 (7)	0.0027 (7)	−0.0012 (7)
C3	0.0766 (17)	0.0344 (11)	0.0432 (11)	0.0146 (10)	0.0073 (11)	0.0130 (9)
N11	0.0255 (7)	0.0208 (6)	0.0239 (6)	0.0034 (5)	−0.0014 (5)	−0.0021 (5)
C11	0.0338 (9)	0.0275 (8)	0.0230 (8)	0.0076 (7)	−0.0034 (7)	0.0008 (6)
C12	0.0371 (9)	0.0287 (8)	0.0192 (7)	0.0064 (7)	−0.0013 (6)	−0.0004 (6)
C13	0.0280 (8)	0.0210 (7)	0.0232 (7)	0.0014 (6)	0.0001 (6)	−0.0010 (6)
C14	0.0279 (8)	0.0277 (8)	0.0240 (8)	0.0078 (6)	−0.0048 (6)	−0.0031 (6)
C15	0.0292 (8)	0.0281 (8)	0.0211 (7)	0.0053 (6)	−0.0048 (6)	−0.0044 (6)
C16	0.0283 (8)	0.0241 (7)	0.0235 (7)	−0.0008 (6)	0.0000 (6)	−0.0058 (6)
C17	0.0229 (8)	0.0223 (7)	0.0262 (8)	0.0002 (6)	−0.0023 (6)	−0.0068 (6)
C18	0.0278 (8)	0.0250 (8)	0.0361 (9)	0.0009 (6)	0.0023 (7)	−0.0016 (7)
C19	0.0414 (11)	0.0280 (9)	0.0477 (11)	0.0002 (8)	0.0017 (9)	0.0040 (8)
C20	0.0456 (11)	0.0236 (8)	0.0495 (11)	0.0083 (8)	−0.0084 (9)	−0.0052 (8)
C21	0.0304 (9)	0.0328 (9)	0.0450 (11)	0.0082 (7)	−0.0051 (8)	−0.0162 (8)
C22	0.0265 (8)	0.0308 (8)	0.0305 (8)	0.0003 (7)	0.0008 (7)	−0.0108 (7)
O11	0.0517 (8)	0.0352 (7)	0.0254 (6)	0.0055 (6)	0.0083 (6)	−0.0005 (5)

Geometric parameters (Å, º) top

Co1—N1ⁱ	2.0520 (15)	C13—C14	1.393 (2)
Co1—N1	2.0520 (15)	C13—C16	1.506 (2)
Co1—N2	2.1647 (15)	C14—C15	1.388 (2)
Co1—N2ⁱ	2.1648 (15)	C14—H14	0.9500
Co1—N11ⁱ	2.1831 (13)	C15—H15	0.9500
Co1—N11	2.1831 (13)	C16—O11	1.218 (2)
N1—C1	1.155 (2)	C16—C17	1.485 (2)
C1—S1	1.6244 (18)	C17—C18	1.394 (2)
N2—C2	1.135 (2)	C17—C22	1.406 (2)
C2—C3	1.453 (3)	C18—C19	1.392 (3)
C3—H3A	0.9800	C18—H18	0.9500
C3—H3B	0.9800	C19—C20	1.380 (3)
C3—H3C	0.9800	C19—H19	0.9500
N11—C15	1.341 (2)	C20—C21	1.392 (3)
N11—C11	1.341 (2)	C20—H20	0.9500
C11—C12	1.386 (2)	C21—C22	1.384 (3)
C11—H11	0.9500	C21—H21	0.9500
C12—C13	1.392 (2)	C22—H22	0.9500
C12—H12	0.9500

N1ⁱ—Co1—N1	180.0	C11—C12—H12	120.3
N1ⁱ—Co1—N2	91.13 (6)	C13—C12—H12	120.3
N1—Co1—N2	88.88 (6)	C12—C13—C14	118.03 (15)
N1ⁱ—Co1—N2ⁱ	88.87 (6)	C12—C13—C16	117.70 (14)
N1—Co1—N2ⁱ	91.13 (6)	C14—C13—C16	124.24 (15)
N2—Co1—N2ⁱ	180.0	C15—C14—C13	118.79 (15)
N1ⁱ—Co1—N11ⁱ	88.05 (6)	C15—C14—H14	120.6
N1—Co1—N11ⁱ	91.95 (6)	C13—C14—H14	120.6
N2—Co1—N11ⁱ	88.24 (5)	N11—C15—C14	123.27 (15)
N2ⁱ—Co1—N11ⁱ	91.76 (5)	N11—C15—H15	118.4
N1ⁱ—Co1—N11	91.95 (6)	C14—C15—H15	118.4
N1—Co1—N11	88.05 (6)	O11—C16—C17	120.68 (15)
N2—Co1—N11	91.76 (5)	O11—C16—C13	118.05 (15)
N2ⁱ—Co1—N11	88.24 (5)	C17—C16—C13	121.22 (14)
N11ⁱ—Co1—N11	180.00 (5)	C18—C17—C22	119.48 (16)
C1—N1—Co1	162.48 (14)	C18—C17—C16	122.27 (15)
N1—C1—S1	178.75 (18)	C22—C17—C16	118.06 (15)
C2—N2—Co1	172.91 (16)	C19—C18—C17	119.76 (17)
N2—C2—C3	178.8 (2)	C19—C18—H18	120.1
C2—C3—H3A	109.5	C17—C18—H18	120.1
C2—C3—H3B	109.5	C20—C19—C18	120.58 (19)
H3A—C3—H3B	109.5	C20—C19—H19	119.7
C2—C3—H3C	109.5	C18—C19—H19	119.7
H3A—C3—H3C	109.5	C19—C20—C21	119.97 (18)
H3B—C3—H3C	109.5	C19—C20—H20	120.0
C15—N11—C11	117.74 (14)	C21—C20—H20	120.0
C15—N11—Co1	123.36 (11)	C22—C21—C20	120.19 (17)
C11—N11—Co1	118.85 (11)	C22—C21—H21	119.9
N11—C11—C12	122.79 (15)	C20—C21—H21	119.9
N11—C11—H11	118.6	C21—C22—C17	120.00 (17)
C12—C11—H11	118.6	C21—C22—H22	120.0
C11—C12—C13	119.35 (15)	C17—C22—H22	120.0

Symmetry code: (i) −x+1, −y, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3A···S1ⁱⁱ	0.98	2.85	3.771 (3)	156
C11—H11···O11ⁱⁱⁱ	0.95	2.49	3.193 (2)	131

Symmetry codes: (ii) x, y−1, z; (iii) −x+1/2, y−1/2, −z+3/2.

Acknowledgements

We thank Professor Dr Wolfgang Bensch for access to his experimental facilities.

Funding information

Funding for this research was provided by: Deutsche Forschungsgemeinschaft (award No. NA 720/5–1); State of Schleswig–Holstein

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