Crystal structure of tetra­aqua­bis­(thio­cyanato-κN)nickel(II)–2,5-di­methyl­pyrazine (1/4)

Suckert, S.; Wriedt, M.; Jess, I.; Näther, C.

doi:10.1107/S2056989014026991

metal-organic compounds

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Volume 71| Part 2| February 2015| Page m18

doi:10.1107/S2056989014026991

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Crystal structure of tetraaquabis(thiocyanato-κN)nickel(II)–2,5-dimethylpyrazine (1/4)

Stefan Suckert,^a ^* Mario Wriedt,^b Inke Jess ^a and Christian Näther ^a

^aInstitut für Anorganische Chemie, Christian-Albrechts-Universität Kiel, Max-Eyth-Strasse 2, 24118 Kiel, Germany, and ^bDepartment of Chemistry & Biomolecular Science, Clarkson University, Potsdam, NY 13699, USA
^*Correspondence e-mail: ssuckert@ac.uni-kiel.de

Edited by S. Parkin, University of Kentucky, USA (Received 3 December 2014; accepted 9 December 2014; online 3 January 2015)

In the crystal structure of the title compound, [Ni(NCS)₂(H₂O)₄]·4C₆H₈N₂, the Ni^II cations are coordinated by four water ligands and two trans-coordinated terminally N-bonded thiocyanate anions in a slightly distorted octahedral geometry. The asymmetric unit consists of a Ni²⁺ cation located on a centre of inversion, two water molecules and one thiocyanate ligand, as well as two uncoordinated 2,5-dimethylpyrazine ligands in general positions. In the crystal, discrete complex molecules are linked into a three-dimensional network by O—H⋯N hydrogen bonding between the water H atoms and the 2,5-dimethylpyrazine N atoms.

Keywords: crystal structure; thiocyanat; nickel(II) complex; 2,5-dimethylpyrazine; hydrogen bonding.

CCDC reference: 1038309

1. Related literature

For background information on the design and preparation of coordination polymers, see Näther et al. (2013 ). For a different structure with thiocyanates and 2,5-dimethylpyrazine, see: Otieno et al. (2003 ).

2. Experimental

2.1. Crystal data

[Ni(NCS)₂(H₂O)₄]·4C₆H₈N₂
M_r = 679.51
Orthorhombic, P b c a
a = 13.0731 (6) Å
b = 14.7989 (8) Å
c = 17.3092 (11) Å
V = 3348.8 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.75 mm⁻¹
T = 170 K
0.12 × 0.10 × 0.08 mm

2.2. Data collection

Stoe IPDS-1 diffractometer
Absorption correction: numerical (X-SHAPE and X-RED32; Stoe & Cie, 2008 ) T_min = 0.912, T_max = 0.938
21266 measured reflections
4041 independent reflections
3146 reflections with I > 2σ(I)
R_int = 0.035

2.3. Refinement

R[F² > 2σ(F²)] = 0.036
wR(F²) = 0.100
S = 1.02
4041 reflections
201 parameters
H-atom parameters constrained
Δρ_max = 0.35 e Å⁻³
Δρ_min = −0.40 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1O1⋯N12	0.84	1.99	2.8284 (18)	174
O1—H2O1⋯N11ⁱ	0.84	2.06	2.8963 (18)	173
O2—H1O2⋯N2ⁱⁱ	0.84	2.00	2.8286 (19)	169
O2—H2O2⋯N1ⁱⁱⁱ	0.84	2.03	2.8665 (19)	176
Symmetry codes: (i) $[x+{\script{1\over 2}}, y, -z+{\script{1\over 2}}]$ ; (ii) -x+1, -y+1, -z+1; (iii) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, z]$ .

Data collection: X-AREA (Stoe & Cie, 2008); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP in SHELXTL (Sheldrick, 2008) and DIAMOND (Brandenburg, 1999 ); software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

CCDC reference: 1038309

Crystal structure: contains datablocks I, global. DOI: 10.1107/S2056989014026991/pk2540sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S2056989014026991/pk2540Isup2.hkl

checkCIF report

Synthesis and crystallization top

NiSO₄.6 H₂O and 2,5-dimethylpyrazine were purchased from Merck and Ba(NCS)₂.3 H₂O was purchased from Alfa Aesar. Ni(NCS)₂ was synthesized by stirring 17.5 g (56.91 mmol) Ba(NCS)₂.3 H₂O and 15.00 g (57.03 mmol) NiSO₄.6 H₂O in 500 ml H₂O at RT for two hours. The white residue of BaSO₄ was filtered of and the solvent removed with a rotary evaporator. The homogeneity of the product was investigated by X-ray powder diffraction and elemental analysis. The title compound was prepared by the reaction of (0.15 mmol) 27.8 mg Ni(NCS)₂ and (0.9 mmol) 97.5 µl 2,5-dimethylpyrazine at RT. After a few days blue block shaped crystals of the title compound were obtained.

Refinement top

The C—H H atoms were positioned with idealized geometry (methyl H atoms allowed to rotate but not to tip) and were refined using a riding model with C—H = 0.95 Å for aromatic and C—H = 0.98 Å for methyl. Water hydrogen atoms were found in difference-electron density maps and fixed (SHELXL command AFIX 3). U_iso(H) values were set to either 1.2U_eq or 1.5U_eq (-CH₃, H₂O) of the attached parent atom.

Related literature top

For background information on the design and preparation of coordination polymers, see Näther et al. (2013). For a different structure with thiocyanates and 2,5-dimethylpyrazine, see: Otieno et al. (2003).

Computing details top

Data collection: X-AREA (Stoe & Cie, 2008); cell refinement: X-AREA (Stoe & Cie, 2008); data reduction: X-AREA (Stoe & Cie, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP in SHELXTL (Sheldrick, 2008) and DIAMOND (Brandenburg, 1999); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

	Fig. 1. Part of the crystal structure of the title compound with labelling and displacement ellipsoids drawn at the 50% probability level. Symmetry code: i = x+1,-y+1,-z+1.
	Fig. 2. Crystal structure of the title compound with view along the crystallographic a axis. Hydrogen bonding is shown as dashed lines and for clarity only the O-H H atoms are shown.

Tetraaquabis(thiocyanato-κN)nickel(II)–2,5-dimethylpyrazine (1/4) top

Crystal data top

[Ni(NCS)₂(H₂O)₄]·4C₆H₈N₂	F(000) = 1432
M_r = 679.51	D_x = 1.348 Mg m⁻³
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 21266 reflections
a = 13.0731 (6) Å	θ = 2.8–28.1°
b = 14.7989 (8) Å	µ = 0.75 mm⁻¹
c = 17.3092 (11) Å	T = 170 K
V = 3348.8 (3) Å³	Block, blue
Z = 4	0.12 × 0.10 × 0.08 mm

Data collection top

Stoe IPDS-1 diffractometer	4041 independent reflections
Radiation source: fine-focus sealed tube	3146 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.035
ϕ scans	θ_max = 28.1°, θ_min = 2.8°
Absorption correction: numerical (X-SHAPE and X-RED32; Stoe & Cie, 2008)	h = −17→15
T_min = 0.912, T_max = 0.938	k = −19→19
21266 measured reflections	l = −22→22

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.036	H-atom parameters constrained
wR(F²) = 0.100	w = 1/[σ²(F_o²) + (0.0627P)² + 0.7837P] where P = (F_o² + 2F_c²)/3
S = 1.02	(Δ/σ)_max = 0.001
4041 reflections	Δρ_max = 0.35 e Å⁻³
201 parameters	Δρ_min = −0.40 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0068 (8)

Crystal data top

[Ni(NCS)₂(H₂O)₄]·4C₆H₈N₂	V = 3348.8 (3) Å³
M_r = 679.51	Z = 4
Orthorhombic, Pbca	Mo Kα radiation
a = 13.0731 (6) Å	µ = 0.75 mm⁻¹
b = 14.7989 (8) Å	T = 170 K
c = 17.3092 (11) Å	0.12 × 0.10 × 0.08 mm

Data collection top

Stoe IPDS-1 diffractometer	4041 independent reflections
Absorption correction: numerical (X-SHAPE and X-RED32; Stoe & Cie, 2008)	3146 reflections with I > 2σ(I)
T_min = 0.912, T_max = 0.938	R_int = 0.035
21266 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.036	0 restraints
wR(F²) = 0.100	H-atom parameters constrained
S = 1.02	Δρ_max = 0.35 e Å⁻³
4041 reflections	Δρ_min = −0.40 e Å⁻³
201 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.

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 > 2sigma(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

	x	y	z	U_iso*/U_eq
Ni1	0.5000	0.5000	0.5000	0.01215 (11)
N21	0.34876 (11)	0.53353 (10)	0.50818 (8)	0.0178 (3)
C21	0.26112 (13)	0.54542 (11)	0.50572 (8)	0.0161 (3)
S21	0.13689 (3)	0.56120 (4)	0.50416 (3)	0.02775 (13)
O1	0.51049 (8)	0.58972 (8)	0.40668 (6)	0.0160 (2)
H1O1	0.4561	0.5882	0.3809	0.024*
H2O1	0.5589	0.5854	0.3750	0.024*
O2	0.54012 (9)	0.60597 (8)	0.57432 (6)	0.0162 (2)
H1O2	0.6015	0.6200	0.5663	0.024*
H2O2	0.5025	0.6507	0.5650	0.024*
N1	0.09222 (12)	0.25396 (10)	0.53656 (9)	0.0231 (3)
N2	0.26379 (12)	0.32843 (10)	0.46598 (9)	0.0223 (3)
C1	0.18340 (14)	0.25266 (11)	0.57207 (10)	0.0211 (3)
C2	0.26824 (14)	0.28976 (12)	0.53578 (11)	0.0227 (4)
H2	0.3323	0.2876	0.5616	0.027*
C3	0.17233 (14)	0.33146 (11)	0.43120 (10)	0.0210 (3)
C4	0.08758 (14)	0.29358 (12)	0.46734 (11)	0.0235 (4)
H4	0.0234	0.2960	0.4416	0.028*
C5	0.18951 (17)	0.20962 (14)	0.65016 (11)	0.0321 (4)
H5A	0.1634	0.2517	0.6892	0.048*
H5B	0.2609	0.1947	0.6618	0.048*
H5C	0.1483	0.1543	0.6506	0.048*
C6	0.16595 (17)	0.37609 (14)	0.35372 (11)	0.0328 (4)
H6A	0.1624	0.4418	0.3605	0.049*
H6B	0.1045	0.3551	0.3267	0.049*
H6C	0.2267	0.3606	0.3233	0.049*
N11	0.16959 (11)	0.58969 (10)	0.20976 (8)	0.0228 (3)
N12	0.33677 (12)	0.58344 (10)	0.30944 (8)	0.0211 (3)
C11	0.16897 (13)	0.63643 (11)	0.27609 (10)	0.0208 (3)
C12	0.25374 (14)	0.63271 (12)	0.32501 (9)	0.0203 (3)
H12	0.2523	0.6668	0.3715	0.024*
C13	0.33614 (14)	0.53519 (12)	0.24377 (10)	0.0207 (3)
C14	0.25231 (14)	0.53952 (13)	0.19461 (10)	0.0225 (4)
H14	0.2538	0.5053	0.1482	0.027*
C15	0.07737 (16)	0.69264 (15)	0.29538 (13)	0.0374 (5)
H15A	0.0305	0.6935	0.2512	0.056*
H15B	0.0992	0.7545	0.3072	0.056*
H15C	0.0424	0.6668	0.3403	0.056*
C16	0.42685 (16)	0.47645 (15)	0.22664 (13)	0.0332 (4)
H16A	0.4875	0.5144	0.2194	0.050*
H16B	0.4140	0.4417	0.1795	0.050*
H16C	0.4383	0.4349	0.2699	0.050*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ni1	0.00735 (16)	0.01786 (16)	0.01122 (15)	0.00033 (10)	−0.00024 (9)	0.00008 (10)
N21	0.0123 (7)	0.0226 (7)	0.0185 (7)	0.0012 (5)	0.0013 (5)	−0.0007 (5)
C21	0.0155 (8)	0.0178 (8)	0.0150 (7)	0.0015 (6)	0.0008 (6)	−0.0004 (6)
S21	0.0102 (2)	0.0405 (3)	0.0326 (3)	0.00601 (18)	−0.00014 (16)	−0.00175 (19)
O1	0.0108 (5)	0.0242 (6)	0.0131 (5)	−0.0002 (4)	0.0000 (4)	0.0033 (4)
O2	0.0121 (5)	0.0196 (5)	0.0170 (5)	0.0007 (4)	−0.0014 (4)	−0.0024 (4)
N1	0.0170 (7)	0.0221 (7)	0.0300 (8)	−0.0023 (6)	0.0024 (6)	−0.0015 (6)
N2	0.0178 (7)	0.0197 (7)	0.0293 (7)	−0.0027 (6)	0.0026 (6)	−0.0032 (6)
C1	0.0228 (8)	0.0178 (7)	0.0228 (8)	−0.0007 (7)	−0.0004 (6)	−0.0046 (6)
C2	0.0167 (8)	0.0225 (8)	0.0291 (9)	−0.0016 (7)	−0.0039 (7)	−0.0045 (7)
C3	0.0196 (8)	0.0171 (7)	0.0262 (8)	0.0017 (7)	0.0014 (7)	−0.0031 (6)
C4	0.0149 (8)	0.0251 (8)	0.0306 (9)	0.0005 (7)	−0.0018 (7)	0.0001 (7)
C5	0.0392 (12)	0.0327 (10)	0.0245 (9)	−0.0022 (9)	−0.0025 (8)	0.0009 (7)
C6	0.0359 (11)	0.0327 (10)	0.0298 (10)	0.0014 (9)	−0.0009 (8)	0.0057 (8)
N11	0.0184 (7)	0.0299 (8)	0.0201 (7)	0.0006 (6)	−0.0050 (6)	−0.0042 (6)
N12	0.0207 (7)	0.0256 (7)	0.0170 (6)	−0.0020 (6)	−0.0046 (5)	0.0009 (5)
C11	0.0189 (8)	0.0226 (8)	0.0209 (8)	−0.0012 (7)	−0.0006 (6)	−0.0015 (6)
C12	0.0226 (8)	0.0234 (8)	0.0151 (7)	−0.0032 (7)	−0.0009 (6)	−0.0023 (6)
C13	0.0184 (8)	0.0241 (8)	0.0198 (8)	−0.0004 (7)	−0.0023 (6)	−0.0006 (6)
C14	0.0211 (9)	0.0290 (9)	0.0173 (7)	0.0001 (7)	−0.0033 (7)	−0.0060 (6)
C15	0.0285 (11)	0.0413 (12)	0.0426 (12)	0.0099 (9)	−0.0016 (9)	−0.0125 (9)
C16	0.0228 (10)	0.0382 (10)	0.0386 (11)	0.0087 (9)	−0.0051 (8)	−0.0071 (9)

Geometric parameters (Å, º) top

Ni1—N21	2.0434 (15)	C5—H5A	0.9800
Ni1—N21ⁱ	2.0434 (15)	C5—H5B	0.9800
Ni1—O2	2.0951 (11)	C5—H5C	0.9800
Ni1—O2ⁱ	2.0951 (11)	C6—H6A	0.9800
Ni1—O1	2.0954 (11)	C6—H6B	0.9800
Ni1—O1ⁱ	2.0954 (11)	C6—H6C	0.9800
N21—C21	1.160 (2)	N11—C14	1.338 (2)
C21—S21	1.6411 (18)	N11—C11	1.340 (2)
O1—H1O1	0.8399	N12—C12	1.335 (2)
O1—H2O1	0.8400	N12—C13	1.342 (2)
O2—H1O2	0.8399	C11—C12	1.396 (2)
O2—H2O2	0.8400	C11—C15	1.496 (3)
N1—C4	1.335 (3)	C12—H12	0.9500
N1—C1	1.341 (2)	C13—C14	1.389 (2)
N2—C2	1.338 (2)	C13—C16	1.500 (3)
N2—C3	1.339 (2)	C14—H14	0.9500
C1—C2	1.388 (2)	C15—H15A	0.9800
C1—C5	1.496 (3)	C15—H15B	0.9800
C2—H2	0.9500	C15—H15C	0.9800
C3—C4	1.390 (2)	C16—H16A	0.9800
C3—C6	1.497 (3)	C16—H16B	0.9800
C4—H4	0.9500	C16—H16C	0.9800

N21—Ni1—N21ⁱ	180.0	C1—C5—H5B	109.5
N21—Ni1—O2	91.03 (5)	H5A—C5—H5B	109.5
N21ⁱ—Ni1—O2	88.97 (5)	C1—C5—H5C	109.5
N21—Ni1—O2ⁱ	88.97 (5)	H5A—C5—H5C	109.5
N21ⁱ—Ni1—O2ⁱ	91.03 (5)	H5B—C5—H5C	109.5
O2—Ni1—O2ⁱ	180.00 (4)	C3—C6—H6A	109.5
N21—Ni1—O1	87.87 (5)	C3—C6—H6B	109.5
N21ⁱ—Ni1—O1	92.13 (5)	H6A—C6—H6B	109.5
O2—Ni1—O1	89.01 (5)	C3—C6—H6C	109.5
O2ⁱ—Ni1—O1	90.99 (5)	H6A—C6—H6C	109.5
N21—Ni1—O1ⁱ	92.13 (5)	H6B—C6—H6C	109.5
N21ⁱ—Ni1—O1ⁱ	87.87 (5)	C14—N11—C11	117.34 (15)
O2—Ni1—O1ⁱ	90.99 (5)	C12—N12—C13	117.16 (15)
O2ⁱ—Ni1—O1ⁱ	89.01 (5)	N11—C11—C12	119.63 (16)
O1—Ni1—O1ⁱ	180.00 (5)	N11—C11—C15	118.88 (16)
C21—N21—Ni1	171.90 (14)	C12—C11—C15	121.48 (16)
N21—C21—S21	178.72 (15)	N12—C12—C11	123.00 (15)
Ni1—O1—H1O1	109.7	N12—C12—H12	118.5
Ni1—O1—H2O1	120.4	C11—C12—H12	118.5
H1O1—O1—H2O1	106.7	N12—C13—C14	119.93 (16)
Ni1—O2—H1O2	108.8	N12—C13—C16	118.09 (16)
Ni1—O2—H2O2	108.9	C14—C13—C16	121.97 (16)
H1O2—O2—H2O2	109.5	N11—C14—C13	122.91 (16)
C4—N1—C1	117.25 (15)	N11—C14—H14	118.5
C2—N2—C3	117.32 (15)	C13—C14—H14	118.5
N1—C1—C2	119.81 (16)	C11—C15—H15A	109.5
N1—C1—C5	117.87 (17)	C11—C15—H15B	109.5
C2—C1—C5	122.31 (17)	H15A—C15—H15B	109.5
N2—C2—C1	122.89 (16)	C11—C15—H15C	109.5
N2—C2—H2	118.6	H15A—C15—H15C	109.5
C1—C2—H2	118.6	H15B—C15—H15C	109.5
N2—C3—C4	119.71 (17)	C13—C16—H16A	109.5
N2—C3—C6	117.85 (17)	C13—C16—H16B	109.5
C4—C3—C6	122.44 (17)	H16A—C16—H16B	109.5
N1—C4—C3	122.99 (17)	C13—C16—H16C	109.5
N1—C4—H4	118.5	H16A—C16—H16C	109.5
C3—C4—H4	118.5	H16B—C16—H16C	109.5
C1—C5—H5A	109.5

Symmetry code: (i) −x+1, −y+1, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O1···N12	0.84	1.99	2.8284 (18)	174
O1—H2O1···N11ⁱⁱ	0.84	2.06	2.8963 (18)	173
O2—H1O2···N2ⁱ	0.84	2.00	2.8286 (19)	169
O2—H2O2···N1ⁱⁱⁱ	0.84	2.03	2.8665 (19)	176

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O1···N12	0.84	1.99	2.8284 (18)	173.7
O1—H2O1···N11ⁱ	0.84	2.06	2.8963 (18)	172.5
O2—H1O2···N2ⁱⁱ	0.84	2.00	2.8286 (19)	169.0
O2—H2O2···N1ⁱⁱⁱ	0.84	2.03	2.8665 (19)	176.3

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

Acknowledgements

We gratefully acknowledge financial support by the DFG (project No. NA 720/5-1) and the State of Schleswig–Holstein. We thank Professor Dr Wolfgang Bensch for access to his experimental facilities.

References

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Volume 71| Part 2| February 2015| Page m18

doi:10.1107/S2056989014026991

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

Crystal structure of tetra­aqua­bis­­(thio­cyanato-κN)nickel(II)–2,5-di­methyl­pyrazine (1/4)

1. Related literature

2. Experimental

2.1. Crystal data

2.2. Data collection

2.3. Refinement

Supporting information

Acknowledgements

References

metal-organic compounds

Crystal structure of tetraaquabis(thiocyanato-κN)nickel(II)–2,5-dimethylpyrazine (1/4)