Tetra­kis(pyridazine-κN)bis­(seleno­cyanato-κN)nickel(II) pyridazine disolvate

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

doi:10.1107/S1600536812028036

metal-organic compounds

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ISSN: 2056-9890

Volume 68| Part 7| July 2012| Page m969

https://doi.org/10.1107/S1600536812028036

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Tetrakis(pyridazine-κN)bis(selenocyanato-κN)nickel(II) pyridazine disolvate

Susanne Wöhlert,^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 ^bDepartement of Chemistry, Texas A&M University, College Station, Texas 77843, USA
^*Correspondence e-mail: swoehlert@ac.uni-kiel.de

(Received 18 June 2012; accepted 20 June 2012; online 23 June 2012)

The reaction of nickel(II) nitrate with potassium selenocyanate and pyridazine leads to crystals of the title compound, [Ni(NCSe)₂(C₄H₄N₂)₄]·2C₄H₄N₂. The Ni^II atom is coordinated by two terminal N-bonded selenocyanate anions and four pyridazine ligands within a slightly distorted octahedral geometry. The crystal structure contains two crystallographically independent pyridazine molecules in cavities of the structure, which are not coordinated to the metal centres. The structure is pseudo-C-centered due to the positioning of the discrete coordination complexes; the non-coordinating pyridazine molecules, however, break the C-centering. In the subcell, these ligands are disordered around centres of inversion, which do not coincide with the mid-point of the molecules.

Related literature

For the synthesis, structures and properties of related coordination compounds see: Boeckmann & Näther (2010 , 2011 ); Wöhlert et al. (2011 , 2012 ).

Experimental

Crystal data

[Ni(NCSe)₂(C₄H₄N₂)₄]·2C₄H₄N₂
M_r = 749.22
Triclinic, $[P \overline 1]$
a = 11.2923 (15) Å
b = 12.0868 (14) Å
c = 12.8220 (15) Å
α = 62.324 (9)°
β = 88.427 (10)°
γ = 88.512 (10)°
V = 1549.1 (3) Å³
Z = 2
Mo Kα radiation
μ = 3.02 mm⁻¹
T = 293 K
0.25 × 0.14 × 0.10 mm

Data collection

Stoe IPDS-2 diffractometer
Absorption correction: numerical (X-SHAPE and X-RED32; Stoe & Cie, 2008 ) T_min = 0.243, T_max = 0.572
15038 measured reflections
6534 independent reflections
4010 reflections with I > 2σ(I)
R_int = 0.068

Refinement

R[F² > 2σ(F²)] = 0.053
wR(F²) = 0.129
S = 1.01
6534 reflections
388 parameters
H-atom parameters constrained
Δρ_max = 0.57 e Å⁻³
Δρ_min = −0.46 e Å⁻³

Table 1
Selected bond lengths (Å)

Ni1—N1	2.051 (4)
Ni1—N2	2.055 (4)
Ni1—N10	2.154 (3)
Ni1—N20	2.129 (3)
Ni1—N30	2.153 (3)
Ni1—N40	2.124 (3)

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: SHELXTL (Sheldrick, 2008) and DIAMOND (Brandenburg, 2011 ); software used to prepare material for publication: XCIF in SHELXTL and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536812028036/vn2044sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812028036/vn2044Isup2.hkl

checkCIF report

Comment top

Recently we have reported on the synthesis and characterization of coordination polymers based on transition metal thio- and selenocyanates. Within this project we investigated the influence of neutral N-donor co-ligands on the structural, thermal and magnetic properties of compounds, in which the metal cations are linked by the anionic ligands (Boeckmann & Näther, 2010, 2011; Wöhlert et al., 2011). In the present investigation we tried to prepare similar compounds using pyridazine as co-ligand, which results in the formation of single crystals of the title compound, which are isotypic to [Ni(NCS)₂(pyridazine)₄].2(pyridazine) reported recently (Wöhlert et al., 2012). In the crystal structure each nickel(II) cation is coordinated by two terminal N-bonded selenocyanato anions and four pyridazine ligands into discrete complexes (Fig. 1). The NiN₆ octahedra are slightly distorted with distances ranging from 2.051 (4) to 2.154 (3) Å and angles between 87.31 (12) ° and 179.88 (15) ° (Table 1). The discrete complexes are arranged in layers, which are separated by additional non-coordinated pyridazine ligands. The shortest intermolecular Ni···Ni distance amounts to 8.2173 (12) Å.

Related literature top

For the synthesis, structures and properties of related coordination compounds see: Boeckmann & Näther (2010, 2011); Wöhlert et al. (2011, 2012).

Experimental top

Nickel(II) nitrate hexahydrate (Ni(NO₃)₂x6H₂O) and potassium selenocyanate (KNCSe) as well as pyridazine were obtained from Alfa Aesar. All chemicals were used without further purification. 0.125 mmol (36.4 mg) Ni(NO₃)₂.6H₂O and 0.25 mmol (36.0 mg) KNCSe were reacted in 2.76 mmol (200 µL) pyridazine, respectively. Purple single crystals of the title compound were obtained after one week.

Structure description top

For the synthesis, structures and properties of related coordination compounds see: Boeckmann & Näther (2010, 2011); Wöhlert et al. (2011, 2012).

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: SHELXTL (Sheldrick, 2008) and DIAMOND (Brandenburg, 2011); software used to prepare material for publication: XCIF in SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

Fig. 1. Crystal structure of the title compound [Ni(NCSe)₂(C₄H₄N₂)₄].2C₄H₄N₂ with labeling and displacement ellipsoids drawn at the 30% probability level.

Tetrakis(pyridazine-κN)bis(selenocyanato-κN)nickel(II) pyridazine disolvate top

Crystal data top

[Ni(NCSe)₂(C₄H₄N₂)₄]·2C₄H₄N₂	Z = 2
M_r = 749.22	F(000) = 748
Triclinic, P1	D_x = 1.606 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 11.2923 (15) Å	Cell parameters from 15038 reflections
b = 12.0868 (14) Å	θ = 1.8–26.8°
c = 12.8220 (15) Å	µ = 3.02 mm⁻¹
α = 62.324 (9)°	T = 293 K
β = 88.427 (10)°	Block, purple
γ = 88.512 (10)°	0.25 × 0.14 × 0.10 mm
V = 1549.1 (3) Å³

Data collection top

Stoe IPDS-2 diffractometer	6534 independent reflections
Radiation source: fine-focus sealed tube	4010 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.068
ω scan	θ_max = 26.8°, θ_min = 1.8°
Absorption correction: numerical (X-SHAPE and X-RED32; Stoe & Cie, 2008)	h = −13→14
T_min = 0.243, T_max = 0.572	k = −15→15
15038 measured reflections	l = −16→16

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.053	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.129	H-atom parameters constrained
S = 1.01	w = 1/[σ²(F_o²) + (0.0583P)²] where P = (F_o² + 2F_c²)/3
6534 reflections	(Δ/σ)_max = 0.001
388 parameters	Δρ_max = 0.57 e Å⁻³
0 restraints	Δρ_min = −0.46 e Å⁻³

Crystal data top

[Ni(NCSe)₂(C₄H₄N₂)₄]·2C₄H₄N₂	γ = 88.512 (10)°
M_r = 749.22	V = 1549.1 (3) Å³
Triclinic, P1	Z = 2
a = 11.2923 (15) Å	Mo Kα radiation
b = 12.0868 (14) Å	µ = 3.02 mm⁻¹
c = 12.8220 (15) Å	T = 293 K
α = 62.324 (9)°	0.25 × 0.14 × 0.10 mm
β = 88.427 (10)°

Data collection top

Stoe IPDS-2 diffractometer	6534 independent reflections
Absorption correction: numerical (X-SHAPE and X-RED32; Stoe & Cie, 2008)	4010 reflections with I > 2σ(I)
T_min = 0.243, T_max = 0.572	R_int = 0.068
15038 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.053	0 restraints
wR(F²) = 0.129	H-atom parameters constrained
S = 1.01	Δρ_max = 0.57 e Å⁻³
6534 reflections	Δρ_min = −0.46 e Å⁻³
388 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

	x	y	z	U_iso*/U_eq
Ni1	0.75263 (4)	0.75195 (4)	0.49428 (5)	0.03775 (13)
N1	0.6464 (3)	0.8464 (3)	0.3514 (3)	0.0482 (8)
C1	0.5667 (4)	0.8920 (3)	0.2914 (4)	0.0449 (9)
Se1	0.44241 (5)	0.96264 (4)	0.19891 (5)	0.06887 (18)
N2	0.8589 (3)	0.6575 (3)	0.6376 (3)	0.0480 (8)
C2	0.9339 (4)	0.6062 (3)	0.7026 (4)	0.0433 (9)
Se2	1.05284 (4)	0.52717 (4)	0.80123 (5)	0.06587 (17)
N10	0.6978 (3)	0.5804 (3)	0.4987 (3)	0.0455 (8)
N11	0.6601 (3)	0.4895 (3)	0.6020 (3)	0.0550 (9)
C11	0.6253 (4)	0.3838 (4)	0.6056 (5)	0.0663 (13)
H11	0.5970	0.3218	0.6772	0.080*
C12	0.6283 (4)	0.3596 (4)	0.5112 (5)	0.0687 (14)
H12	0.6036	0.2835	0.5183	0.082*
C13	0.6688 (5)	0.4513 (5)	0.4069 (5)	0.0743 (15)
H13	0.6742	0.4403	0.3398	0.089*
C14	0.7019 (4)	0.5629 (4)	0.4047 (4)	0.0589 (11)
H14	0.7279	0.6278	0.3337	0.071*
N20	0.6117 (3)	0.7459 (3)	0.6104 (3)	0.0408 (7)
N21	0.5425 (3)	0.8496 (3)	0.5696 (3)	0.0466 (8)
C21	0.4570 (4)	0.8558 (4)	0.6387 (4)	0.0541 (11)
H21	0.4098	0.9277	0.6104	0.065*
C22	0.4334 (4)	0.7615 (4)	0.7510 (4)	0.0623 (12)
H22	0.3721	0.7692	0.7972	0.075*
C23	0.5033 (4)	0.6571 (4)	0.7912 (4)	0.0568 (11)
H23	0.4907	0.5903	0.8655	0.068*
C24	0.5940 (4)	0.6534 (4)	0.7177 (4)	0.0480 (9)
H24	0.6441	0.5837	0.7448	0.058*
N30	0.8051 (3)	0.9236 (3)	0.4909 (3)	0.0456 (8)
N31	0.8360 (3)	1.0191 (3)	0.3876 (3)	0.0557 (9)
C31	0.8674 (4)	1.1253 (4)	0.3867 (5)	0.0661 (13)
H31	0.8906	1.1907	0.3148	0.079*
C32	0.8680 (4)	1.1452 (5)	0.4824 (6)	0.0712 (14)
H32	0.8892	1.2216	0.4768	0.085*
C33	0.8360 (5)	1.0471 (5)	0.5874 (5)	0.0735 (15)
H33	0.8345	1.0536	0.6569	0.088*
C34	0.8056 (4)	0.9371 (4)	0.5858 (4)	0.0581 (11)
H34	0.7845	0.8691	0.6568	0.070*
N40	0.8959 (3)	0.7555 (3)	0.3819 (3)	0.0438 (7)
N41	0.9615 (3)	0.6503 (3)	0.4249 (3)	0.0487 (8)
C41	1.0520 (4)	0.6428 (4)	0.3616 (4)	0.0589 (12)
H41	1.0956	0.5685	0.3908	0.071*
C42	1.0859 (4)	0.7394 (5)	0.2542 (5)	0.0652 (13)
H42	1.1526	0.7319	0.2135	0.078*
C43	1.0186 (4)	0.8460 (4)	0.2098 (4)	0.0603 (12)
H43	1.0364	0.9137	0.1373	0.072*
C44	0.9220 (4)	0.8487 (4)	0.2779 (4)	0.0505 (10)
H44	0.8735	0.9196	0.2487	0.061*
N50	0.8139 (5)	0.8781 (4)	0.9912 (5)	0.0856 (14)
N51	0.8770 (5)	0.8446 (5)	0.9251 (5)	0.0989 (16)
C51	0.8485 (7)	0.7476 (7)	0.9162 (6)	0.103 (2)
H51	0.8955	0.7254	0.8679	0.123*
C52	0.7534 (8)	0.6741 (6)	0.9729 (8)	0.109 (3)
H52	0.7349	0.6046	0.9639	0.131*
C53	0.6881 (6)	0.7093 (5)	1.0433 (7)	0.107 (3)
H53	0.6222	0.6648	1.0856	0.128*
C54	0.7233 (6)	0.8112 (6)	1.0487 (6)	0.0923 (19)
H54	0.6799	0.8361	1.0971	0.111*
N60	1.2999 (4)	0.5993 (4)	1.0408 (4)	0.0718 (11)
N61	1.3853 (4)	0.6604 (4)	1.0600 (4)	0.0741 (12)
C61	1.3687 (5)	0.7775 (5)	1.0313 (5)	0.0755 (15)
H61	1.4294	0.8185	1.0462	0.091*
C62	1.2676 (6)	0.8459 (5)	0.9802 (5)	0.0828 (17)
H62	1.2607	0.9304	0.9593	0.099*
C63	1.1803 (5)	0.7846 (5)	0.9622 (5)	0.0751 (14)
H63	1.1088	0.8241	0.9299	0.090*
C64	1.2007 (5)	0.6605 (5)	0.9935 (5)	0.0729 (14)
H64	1.1411	0.6169	0.9805	0.088*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ni1	0.0371 (2)	0.0319 (2)	0.0395 (2)	0.00175 (16)	0.00078 (17)	−0.01283 (18)
N1	0.048 (2)	0.0464 (18)	0.0447 (19)	0.0053 (16)	−0.0025 (16)	−0.0168 (16)
C1	0.056 (3)	0.0323 (18)	0.043 (2)	−0.0050 (18)	0.0046 (19)	−0.0142 (17)
Se1	0.0648 (3)	0.0556 (3)	0.0712 (4)	0.0030 (2)	−0.0256 (3)	−0.0156 (3)
N2	0.0443 (19)	0.0453 (18)	0.048 (2)	0.0073 (15)	−0.0059 (16)	−0.0165 (16)
C2	0.044 (2)	0.0390 (19)	0.043 (2)	−0.0033 (17)	0.0035 (18)	−0.0166 (18)
Se2	0.0581 (3)	0.0605 (3)	0.0658 (3)	0.0073 (2)	−0.0216 (2)	−0.0175 (3)
N10	0.0373 (18)	0.0401 (16)	0.058 (2)	0.0012 (14)	−0.0016 (15)	−0.0221 (16)
N11	0.062 (2)	0.0395 (17)	0.061 (2)	−0.0087 (16)	0.0092 (18)	−0.0209 (17)
C11	0.062 (3)	0.047 (2)	0.083 (4)	−0.014 (2)	0.014 (3)	−0.024 (2)
C12	0.063 (3)	0.054 (3)	0.101 (4)	−0.010 (2)	0.000 (3)	−0.045 (3)
C13	0.080 (4)	0.079 (3)	0.089 (4)	−0.014 (3)	0.003 (3)	−0.059 (3)
C14	0.061 (3)	0.059 (3)	0.060 (3)	−0.011 (2)	0.003 (2)	−0.030 (2)
N20	0.0432 (18)	0.0324 (14)	0.0427 (18)	0.0033 (13)	−0.0005 (14)	−0.0140 (14)
N21	0.0462 (19)	0.0394 (16)	0.0478 (19)	0.0057 (14)	0.0030 (15)	−0.0154 (15)
C21	0.050 (3)	0.047 (2)	0.062 (3)	0.013 (2)	0.001 (2)	−0.023 (2)
C22	0.059 (3)	0.068 (3)	0.058 (3)	0.006 (2)	0.011 (2)	−0.028 (2)
C23	0.066 (3)	0.051 (2)	0.048 (3)	−0.001 (2)	0.009 (2)	−0.019 (2)
C24	0.052 (2)	0.042 (2)	0.048 (2)	0.0027 (18)	0.0011 (19)	−0.0186 (19)
N30	0.0446 (19)	0.0385 (16)	0.054 (2)	−0.0024 (14)	0.0021 (16)	−0.0213 (16)
N31	0.059 (2)	0.0398 (17)	0.063 (2)	−0.0069 (16)	0.0085 (18)	−0.0194 (17)
C31	0.065 (3)	0.043 (2)	0.086 (4)	−0.006 (2)	0.007 (3)	−0.026 (2)
C32	0.060 (3)	0.058 (3)	0.105 (4)	−0.014 (2)	0.003 (3)	−0.045 (3)
C33	0.073 (3)	0.084 (4)	0.088 (4)	−0.017 (3)	0.001 (3)	−0.060 (3)
C34	0.060 (3)	0.058 (3)	0.062 (3)	−0.012 (2)	0.000 (2)	−0.031 (2)
N40	0.0414 (18)	0.0371 (16)	0.0481 (19)	0.0000 (14)	0.0026 (15)	−0.0159 (15)
N41	0.047 (2)	0.0401 (16)	0.052 (2)	0.0061 (15)	0.0027 (16)	−0.0157 (15)
C41	0.057 (3)	0.058 (3)	0.065 (3)	0.009 (2)	0.006 (2)	−0.032 (2)
C42	0.057 (3)	0.073 (3)	0.064 (3)	0.002 (2)	0.016 (2)	−0.031 (3)
C43	0.068 (3)	0.058 (3)	0.046 (3)	−0.015 (2)	0.016 (2)	−0.017 (2)
C44	0.057 (3)	0.039 (2)	0.047 (2)	−0.0022 (18)	0.000 (2)	−0.0127 (18)
N50	0.084 (3)	0.067 (3)	0.116 (4)	−0.002 (3)	−0.010 (3)	−0.050 (3)
N51	0.088 (4)	0.075 (3)	0.115 (4)	0.010 (3)	0.007 (3)	−0.030 (3)
C51	0.119 (6)	0.105 (5)	0.100 (5)	0.046 (5)	−0.027 (4)	−0.062 (4)
C52	0.129 (6)	0.057 (3)	0.156 (7)	0.027 (4)	−0.089 (6)	−0.058 (4)
C53	0.066 (4)	0.059 (3)	0.156 (7)	−0.011 (3)	−0.016 (4)	−0.015 (4)
C54	0.095 (5)	0.088 (4)	0.094 (5)	0.012 (4)	0.000 (4)	−0.043 (4)
N60	0.080 (3)	0.049 (2)	0.078 (3)	−0.008 (2)	−0.006 (2)	−0.022 (2)
N61	0.072 (3)	0.061 (2)	0.075 (3)	−0.004 (2)	−0.005 (2)	−0.019 (2)
C61	0.082 (4)	0.072 (3)	0.077 (4)	−0.022 (3)	0.002 (3)	−0.037 (3)
C62	0.103 (5)	0.052 (3)	0.091 (4)	−0.002 (3)	0.018 (4)	−0.033 (3)
C63	0.065 (3)	0.075 (3)	0.080 (4)	0.009 (3)	0.007 (3)	−0.032 (3)
C64	0.075 (4)	0.074 (3)	0.072 (4)	−0.025 (3)	0.006 (3)	−0.035 (3)

Geometric parameters (Å, º) top

Ni1—N1	2.051 (4)	C32—C33	1.363 (8)
Ni1—N2	2.055 (4)	C32—H32	0.9300
Ni1—N10	2.154 (3)	C33—C34	1.391 (6)
Ni1—N20	2.129 (3)	C33—H33	0.9300
Ni1—N30	2.153 (3)	C34—H34	0.9300
Ni1—N40	2.124 (3)	N40—C44	1.317 (5)
N1—C1	1.151 (5)	N40—N41	1.339 (4)
C1—Se1	1.786 (5)	N41—C41	1.315 (5)
N2—C2	1.152 (5)	C41—C42	1.381 (7)
C2—Se2	1.794 (4)	C41—H41	0.9300
N10—C14	1.317 (6)	C42—C43	1.362 (6)
N10—N11	1.335 (5)	C42—H42	0.9300
N11—C11	1.326 (5)	C43—C44	1.387 (6)
C11—C12	1.371 (7)	C43—H43	0.9300
C11—H11	0.9300	C44—H44	0.9300
C12—C13	1.357 (8)	N50—N51	1.289 (7)
C12—H12	0.9300	N50—C54	1.301 (8)
C13—C14	1.398 (6)	N51—C51	1.280 (9)
C13—H13	0.9300	C51—C52	1.370 (11)
C14—H14	0.9300	C51—H51	0.9300
N20—C24	1.323 (5)	C52—C53	1.358 (11)
N20—N21	1.348 (4)	C52—H52	0.9300
N21—C21	1.317 (5)	C53—C54	1.336 (9)
C21—C22	1.384 (6)	C53—H53	0.9300
C21—H21	0.9300	C54—H54	0.9300
C22—C23	1.359 (6)	N60—N61	1.324 (6)
C22—H22	0.9300	N60—C64	1.322 (7)
C23—C24	1.386 (6)	N61—C61	1.296 (6)
C23—H23	0.9300	C61—C62	1.380 (8)
C24—H24	0.9300	C61—H61	0.9300
N30—C34	1.301 (5)	C62—C63	1.336 (8)
N30—N31	1.335 (5)	C62—H62	0.9300
N31—C31	1.334 (5)	C63—C64	1.376 (7)
C31—C32	1.356 (7)	C63—H63	0.9300
C31—H31	0.9300	C64—H64	0.9300

N1—Ni1—N2	179.88 (15)	N31—C31—H31	117.4
N1—Ni1—N40	90.53 (13)	C32—C31—H31	117.4
N2—Ni1—N40	89.57 (13)	C31—C32—C33	116.5 (4)
N1—Ni1—N20	90.85 (13)	C31—C32—H32	121.8
N2—Ni1—N20	89.05 (13)	C33—C32—H32	121.8
N40—Ni1—N20	178.62 (14)	C32—C33—C34	117.1 (5)
N1—Ni1—N30	91.64 (13)	C32—C33—H33	121.5
N2—Ni1—N30	88.30 (13)	C34—C33—H33	121.5
N40—Ni1—N30	92.71 (12)	N30—C34—C33	123.9 (5)
N20—Ni1—N30	87.31 (12)	N30—C34—H34	118.0
N1—Ni1—N10	88.17 (13)	C33—C34—H34	118.0
N2—Ni1—N10	91.89 (13)	C44—N40—N41	120.0 (3)
N40—Ni1—N10	88.07 (12)	C44—N40—Ni1	126.0 (3)
N20—Ni1—N10	91.92 (12)	N41—N40—Ni1	114.0 (2)
N30—Ni1—N10	179.20 (13)	C41—N41—N40	118.7 (3)
C1—N1—Ni1	164.0 (3)	N41—C41—C42	123.6 (4)
N1—C1—Se1	179.7 (4)	N41—C41—H41	118.2
C2—N2—Ni1	167.3 (4)	C42—C41—H41	118.2
N2—C2—Se2	178.9 (4)	C43—C42—C41	117.8 (4)
C14—N10—N11	120.1 (3)	C43—C42—H42	121.1
C14—N10—Ni1	122.3 (3)	C41—C42—H42	121.1
N11—N10—Ni1	117.5 (3)	C42—C43—C44	116.7 (4)
C11—N11—N10	118.0 (4)	C42—C43—H43	121.6
N11—C11—C12	124.6 (5)	C44—C43—H43	121.6
N11—C11—H11	117.7	N40—C44—C43	123.1 (4)
C12—C11—H11	117.7	N40—C44—H44	118.4
C13—C12—C11	117.2 (4)	C43—C44—H44	118.4
C13—C12—H12	121.4	N51—N50—C54	119.0 (5)
C11—C12—H12	121.4	C51—N51—N50	119.5 (6)
C12—C13—C14	117.1 (5)	N51—C51—C52	124.4 (7)
C12—C13—H13	121.4	N51—C51—H51	117.8
C14—C13—H13	121.4	C52—C51—H51	117.8
N10—C14—C13	122.9 (5)	C53—C52—C51	115.7 (5)
N10—C14—H14	118.5	C53—C52—H52	122.2
C13—C14—H14	118.5	C51—C52—H52	122.2
C24—N20—N21	120.4 (3)	C54—C53—C52	116.6 (6)
C24—N20—Ni1	124.8 (2)	C54—C53—H53	121.7
N21—N20—Ni1	114.6 (2)	C52—C53—H53	121.7
C21—N21—N20	118.4 (3)	N50—C54—C53	124.8 (7)
N21—C21—C22	123.7 (4)	N50—C54—H54	117.6
N21—C21—H21	118.1	C53—C54—H54	117.6
C22—C21—H21	118.1	N61—N60—C64	118.5 (4)
C23—C22—C21	117.4 (4)	C61—N61—N60	118.9 (5)
C23—C22—H22	121.3	N61—C61—C62	124.9 (5)
C21—C22—H22	121.3	N61—C61—H61	117.6
C22—C23—C24	117.9 (4)	C62—C61—H61	117.6
C22—C23—H23	121.1	C63—C62—C61	116.7 (5)
C24—C23—H23	121.1	C63—C62—H62	121.7
N20—C24—C23	122.1 (4)	C61—C62—H62	121.7
N20—C24—H24	118.9	C62—C63—C64	117.0 (5)
C23—C24—H24	118.9	C62—C63—H63	121.5
C34—N30—N31	119.5 (3)	C64—C63—H63	121.5
C34—N30—Ni1	121.9 (3)	N60—C64—C63	124.1 (5)
N31—N30—Ni1	118.6 (3)	N60—C64—H64	118.0
C31—N31—N30	117.9 (4)	C63—C64—H64	118.0
N31—C31—C32	125.1 (5)

Experimental details

Crystal data
Chemical formula	[Ni(NCSe)₂(C₄H₄N₂)₄]·2C₄H₄N₂
M_r	749.22
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	11.2923 (15), 12.0868 (14), 12.8220 (15)
α, β, γ (°)	62.324 (9), 88.427 (10), 88.512 (10)
V (Å³)	1549.1 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	3.02
Crystal size (mm)	0.25 × 0.14 × 0.10

Data collection
Diffractometer	Stoe IPDS2
Absorption correction	Numerical (X-SHAPE and X-RED32; Stoe & Cie, 2008)
T_min, T_max	0.243, 0.572
No. of measured, independent and observed [I > 2σ(I)] reflections	15038, 6534, 4010
R_int	0.068
(sin θ/λ)_max (Å⁻¹)	0.634

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.053, 0.129, 1.01
No. of reflections	6534
No. of parameters	388
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.57, −0.46

Computer programs: X-AREA (Stoe & Cie, 2008), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008) and DIAMOND (Brandenburg, 2011), XCIF in SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Selected bond lengths (Å) top

Ni1—N1	2.051 (4)	Ni1—N20	2.129 (3)
Ni1—N2	2.055 (4)	Ni1—N30	2.153 (3)
Ni1—N10	2.154 (3)	Ni1—N40	2.124 (3)

Acknowledgements

We gratefully acknowledge financial support by the DFG (project No. NA 720/3–1) and the State of Schleswig–Holstein. We thank Professor Dr Wolfgang Bensch for access to his experimental facilities.

References

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