Bis(N-phenyl­ethane-1,2-diamine)dithio­cyanato­nickel(II)

Wang, C.-Y.; Cao, F.; Wang, P.; Lv, C.-Y.; Wu, X.

doi:10.1107/S1600536809055792

metal-organic compounds

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ISSN: 2056-9890

Volume 66| Part 2| February 2010| Page m119

https://doi.org/10.1107/S1600536809055792

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Bis(N-phenylethane-1,2-diamine)dithiocyanatonickel(II)

Chen-Yi Wang,^a ^* Feng Cao,^a Ping Wang,^a Chun-Yan Lv ^a and Xiang Wu ^a

^aDepartment of Chemistry, Huzhou University, Huzhou 313000, People's Republic of China
^*Correspondence e-mail: chenyi_wang@163.com

(Received 30 December 2009; accepted 30 December 2009; online 9 January 2010)

The asymmetric unit of the title mononuclear Ni^II compound, [Ni(NCS)₂(C₈H₁₂N₂)₂], contains two independent half-molecules, the Ni atoms of which lie on crystallographic inversion centres. Each Ni^II ion is chelated by two N atoms from two N-phenylethane-1,2-diamine ligands and is also coordinated by two N atoms from two thiocyanate ligands, giving a distorted octahedral geometry. In the crystal, molecules are linked into a two-dimensional network parallel to (100) by N—H⋯S interactions.

Related literature

For related structures, see: Lever et al. (1983 ); Brown & Lingafelter (1963 ); Sanni et al. (1987 ).

Experimental

Crystal data

[Ni(NCS)₂(C₈H₁₂N₂)₂]
M_r = 447.26
Triclinic, $[P \overline 1]$
a = 7.9947 (2) Å
b = 9.4708 (3) Å
c = 13.8044 (3) Å
α = 93.045 (1)°
β = 98.258 (1)°
γ = 90.934 (1)°
V = 1032.62 (5) Å³
Z = 2
Mo Kα radiation
μ = 1.16 mm⁻¹
T = 298 K
0.18 × 0.17 × 0.17 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.819, T_max = 0.828
6197 measured reflections
4314 independent reflections
3284 reflections with I > 2σ(I)
R_int = 0.018

Refinement

R[F² > 2σ(F²)] = 0.037
wR(F²) = 0.080
S = 1.03
4314 reflections
253 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.31 e Å⁻³
Δρ_min = −0.26 e Å⁻³

Table 1
Selected bond lengths (Å)

Ni1—N5	2.073 (2)
Ni1—N1	2.094 (2)
Ni1—N2	2.159 (2)
Ni2—N6	2.047 (2)
Ni2—N3	2.104 (2)
Ni2—N4	2.171 (2)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N4—H4A⋯S1ⁱ	0.89 (1)	2.52 (1)	3.393 (2)	168 (3)
N2—H2⋯S2ⁱⁱ	0.90 (1)	2.67 (2)	3.436 (2)	144 (3)
Symmetry codes: (i) x+1, y-1, z; (ii) x-1, y, z.

Data collection: SMART (Bruker, 1998 ); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536809055792/ci5008sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536809055792/ci5008Isup2.hkl

checkCIF report

Comment top

As part of our investigations into novel urease inhibitors, we have synthesized the title compound, a new Ni^II complex. There are two independent half-molecules in the asymmetric unit. Each Ni atom lies on an inversion centre and is chelated by two N atoms from two N-phenylethane-1,2-diamine ligands, and coordinated by two N atoms from two thiocyanate ligands (Fig. 1). While the three trans angles at each Ni centre are 180° by symmetry, the other angles are close to 90° [81.54 (8)°–98.46 (8)°], indicating a slightly distorted octahedral coordination. The Ni—N bond lengths (Table 1) are typical and are comparable with those observed in other similar nickel(II) complexes (Lever et al., 1983; Brown & Lingafelter, 1963; Sanni et al., 1987).

Related literature top

For related structures, see: Lever et al. (1983); Brown & Lingafelter (1963); Sanni et al. (1987).

Experimental top

N-Phenylethane-1,2-diamine (0.2 mmol, 27.2 mg), ammonium thiocyanate (0.2 mmol, 15.2 mg), and Ni(CH₃COO)₂.4H₂O (0.1 mmol, 24.9 mg) were mixed in a MeOH solution with stirring for 30 min at room temperature. After keeping the filtrate in air for five days, green block-shaped crystals were formed at the bottom of the vessel.

Structure description top

For related structures, see: Lever et al. (1983); Brown & Lingafelter (1963); Sanni et al. (1987).

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT (Bruker, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

Fig. 1. View of the two independent half-molecules in the title compound, showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level. Unlabelled atoms in the molecule containing Ni1 are at the symmetry position (-x, 2 - y, -z) and those in the other molecule are at (2 -x, 1 - y, 1 -z).

Bis(N-phenylethane-1,2-diamine)dithiocyanatonickel(II) top

Crystal data top

[Ni(NCS)₂(C₈H₁₂N₂)₂]	Z = 2
M_r = 447.26	F(000) = 468
Triclinic, P1	D_x = 1.438 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.9947 (2) Å	Cell parameters from 1847 reflections
b = 9.4708 (3) Å	θ = 2.5–25.0°
c = 13.8044 (3) Å	µ = 1.16 mm⁻¹
α = 93.045 (1)°	T = 298 K
β = 98.258 (1)°	Block, green
γ = 90.934 (1)°	0.18 × 0.17 × 0.17 mm
V = 1032.62 (5) Å³

Data collection top

Bruker SMART CCD area-detector diffractometer	4314 independent reflections
Radiation source: fine-focus sealed tube	3284 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.018
ω scan	θ_max = 27.0°, θ_min = 1.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→9
T_min = 0.819, T_max = 0.828	k = −12→8
6197 measured reflections	l = −17→17

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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.080	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ²(F_o²) + (0.0256P)² + 0.3717P] where P = (F_o² + 2F_c²)/3
4314 reflections	(Δ/σ)_max = 0.001
253 parameters	Δρ_max = 0.31 e Å⁻³
2 restraints	Δρ_min = −0.26 e Å⁻³

Crystal data top

[Ni(NCS)₂(C₈H₁₂N₂)₂]	γ = 90.934 (1)°
M_r = 447.26	V = 1032.62 (5) Å³
Triclinic, P1	Z = 2
a = 7.9947 (2) Å	Mo Kα radiation
b = 9.4708 (3) Å	µ = 1.16 mm⁻¹
c = 13.8044 (3) Å	T = 298 K
α = 93.045 (1)°	0.18 × 0.17 × 0.17 mm
β = 98.258 (1)°

Data collection top

Bruker SMART CCD area-detector diffractometer	4314 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3284 reflections with I > 2σ(I)
T_min = 0.819, T_max = 0.828	R_int = 0.018
6197 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.037	2 restraints
wR(F²) = 0.080	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	Δρ_max = 0.31 e Å⁻³
4314 reflections	Δρ_min = −0.26 e Å⁻³
253 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	0.0000	1.0000	0.0000	0.03175 (12)
Ni2	1.0000	0.5000	0.5000	0.03243 (12)
S1	0.21085 (10)	1.40198 (7)	0.20456 (5)	0.0487 (2)
S2	1.28479 (10)	0.83224 (9)	0.32626 (6)	0.0600 (2)
N1	0.2337 (3)	0.9430 (2)	−0.04011 (16)	0.0424 (5)
H1A	0.2188	0.9022	−0.1012	0.051*
H1B	0.3009	1.0204	−0.0392	0.051*
N2	0.0504 (3)	0.8295 (2)	0.09707 (15)	0.0348 (5)
N3	1.2463 (3)	0.4484 (2)	0.56125 (16)	0.0444 (6)
H3A	1.3139	0.5263	0.5682	0.053*
H3B	1.2448	0.4147	0.6209	0.053*
N4	1.0325 (3)	0.3174 (2)	0.40317 (16)	0.0372 (5)
N5	0.1256 (3)	1.1389 (2)	0.10846 (17)	0.0460 (6)
N6	1.1013 (3)	0.6271 (2)	0.40688 (16)	0.0435 (6)
C1	0.3124 (3)	0.8433 (3)	0.0301 (2)	0.0452 (7)
H1C	0.3664	0.8947	0.0893	0.054*
H1D	0.3979	0.7902	0.0017	0.054*
C2	0.1773 (3)	0.7435 (3)	0.0544 (2)	0.0411 (6)
H2A	0.1247	0.6904	−0.0044	0.049*
H2B	0.2265	0.6772	0.1010	0.049*
C3	−0.0938 (3)	0.7571 (2)	0.12332 (18)	0.0345 (6)
C4	−0.1649 (3)	0.6357 (3)	0.0722 (2)	0.0419 (6)
H4	−0.1159	0.5953	0.0205	0.050*
C5	−0.3091 (4)	0.5748 (3)	0.0985 (2)	0.0514 (8)
H5	−0.3563	0.4933	0.0640	0.062*
C6	−0.3842 (4)	0.6325 (3)	0.1746 (2)	0.0541 (8)
H6	−0.4811	0.5906	0.1916	0.065*
C7	−0.3129 (4)	0.7538 (3)	0.2254 (2)	0.0498 (7)
H7	−0.3627	0.7941	0.2768	0.060*
C8	−0.1695 (3)	0.8152 (3)	0.2006 (2)	0.0427 (6)
H8	−0.1224	0.8963	0.2356	0.051*
C9	1.3121 (3)	0.3404 (3)	0.4961 (2)	0.0501 (7)
H9A	1.4042	0.2912	0.5325	0.060*
H9B	1.3546	0.3851	0.4426	0.060*
C10	1.1697 (3)	0.2371 (3)	0.4563 (2)	0.0486 (7)
H10A	1.2089	0.1657	0.4124	0.058*
H10B	1.1293	0.1902	0.5096	0.058*
C11	0.8788 (3)	0.2437 (3)	0.36351 (19)	0.0369 (6)
C12	0.8105 (4)	0.1359 (3)	0.4109 (2)	0.0448 (7)
H12	0.8716	0.1011	0.4667	0.054*
C13	0.6509 (4)	0.0801 (3)	0.3749 (2)	0.0532 (8)
H13	0.6059	0.0080	0.4071	0.064*
C14	0.5582 (4)	0.1295 (3)	0.2925 (2)	0.0551 (8)
H14	0.4505	0.0923	0.2697	0.066*
C15	0.6271 (4)	0.2353 (3)	0.2438 (2)	0.0492 (7)
H15	0.5663	0.2686	0.1874	0.059*
C16	0.7864 (3)	0.2914 (3)	0.2791 (2)	0.0428 (6)
H16	0.8321	0.3621	0.2459	0.051*
C17	0.1622 (3)	1.2472 (3)	0.14957 (18)	0.0353 (6)
C18	1.1772 (3)	0.7109 (3)	0.37193 (18)	0.0372 (6)
H2	0.104 (4)	0.874 (3)	0.1524 (14)	0.080*
H4A	1.076 (4)	0.353 (3)	0.3537 (17)	0.080*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ni1	0.0354 (3)	0.0256 (2)	0.0348 (3)	−0.00085 (18)	0.00618 (19)	0.00362 (18)
Ni2	0.0350 (3)	0.0293 (2)	0.0333 (3)	−0.00465 (19)	0.00483 (19)	0.00667 (19)
S1	0.0621 (5)	0.0367 (4)	0.0477 (4)	−0.0126 (3)	0.0130 (4)	−0.0036 (3)
S2	0.0544 (5)	0.0756 (6)	0.0502 (5)	−0.0305 (4)	0.0059 (4)	0.0199 (4)
N1	0.0442 (13)	0.0376 (12)	0.0484 (14)	0.0029 (10)	0.0135 (11)	0.0114 (10)
N2	0.0373 (12)	0.0311 (11)	0.0371 (13)	−0.0011 (9)	0.0079 (10)	0.0054 (9)
N3	0.0426 (13)	0.0445 (13)	0.0439 (14)	−0.0035 (10)	−0.0003 (10)	0.0028 (11)
N4	0.0372 (12)	0.0370 (12)	0.0374 (13)	−0.0042 (10)	0.0050 (10)	0.0053 (10)
N5	0.0558 (15)	0.0365 (13)	0.0436 (14)	−0.0056 (11)	0.0019 (11)	0.0002 (11)
N6	0.0518 (15)	0.0391 (13)	0.0415 (13)	−0.0066 (11)	0.0126 (11)	0.0075 (10)
C1	0.0382 (16)	0.0445 (16)	0.0552 (18)	0.0092 (12)	0.0096 (13)	0.0145 (13)
C2	0.0434 (16)	0.0325 (14)	0.0494 (17)	0.0092 (12)	0.0090 (13)	0.0120 (12)
C3	0.0353 (14)	0.0312 (13)	0.0375 (14)	0.0001 (11)	0.0026 (11)	0.0132 (11)
C4	0.0494 (17)	0.0345 (14)	0.0419 (16)	0.0006 (12)	0.0049 (13)	0.0080 (12)
C5	0.0481 (18)	0.0373 (16)	0.067 (2)	−0.0073 (13)	−0.0003 (15)	0.0110 (14)
C6	0.0368 (16)	0.0563 (19)	0.071 (2)	−0.0027 (14)	0.0066 (15)	0.0288 (17)
C7	0.0505 (18)	0.0519 (18)	0.0511 (18)	0.0062 (14)	0.0161 (14)	0.0153 (14)
C8	0.0485 (17)	0.0408 (15)	0.0411 (16)	0.0003 (12)	0.0124 (13)	0.0089 (12)
C9	0.0384 (16)	0.0549 (18)	0.0569 (19)	0.0059 (13)	0.0047 (14)	0.0046 (15)
C10	0.0473 (17)	0.0423 (16)	0.0556 (19)	0.0067 (13)	0.0061 (14)	−0.0004 (14)
C11	0.0413 (15)	0.0308 (13)	0.0386 (15)	−0.0011 (11)	0.0084 (12)	−0.0030 (11)
C12	0.0545 (18)	0.0361 (15)	0.0440 (16)	−0.0061 (13)	0.0080 (13)	0.0040 (12)
C13	0.061 (2)	0.0409 (16)	0.059 (2)	−0.0167 (14)	0.0143 (16)	0.0009 (14)
C14	0.0462 (18)	0.0518 (18)	0.065 (2)	−0.0127 (14)	0.0053 (15)	−0.0053 (16)
C15	0.0478 (18)	0.0529 (18)	0.0453 (17)	0.0017 (14)	0.0027 (13)	−0.0008 (14)
C16	0.0440 (16)	0.0426 (15)	0.0422 (16)	−0.0039 (12)	0.0070 (13)	0.0059 (12)
C17	0.0330 (14)	0.0420 (15)	0.0318 (14)	−0.0013 (11)	0.0054 (11)	0.0091 (12)
C18	0.0376 (15)	0.0402 (15)	0.0335 (14)	−0.0013 (12)	0.0048 (11)	0.0014 (11)

Geometric parameters (Å, º) top

Ni1—N5	2.073 (2)	C1—H1D	0.97
Ni1—N5ⁱ	2.073 (2)	C2—H2A	0.97
Ni1—N1ⁱ	2.094 (2)	C2—H2B	0.97
Ni1—N1	2.094 (2)	C3—C4	1.386 (3)
Ni1—N2ⁱ	2.159 (2)	C3—C8	1.393 (4)
Ni1—N2	2.159 (2)	C4—C5	1.384 (4)
Ni2—N6ⁱⁱ	2.047 (2)	C4—H4	0.93
Ni2—N6	2.047 (2)	C5—C6	1.376 (4)
Ni2—N3ⁱⁱ	2.104 (2)	C5—H5	0.93
Ni2—N3	2.104 (2)	C6—C7	1.384 (4)
Ni2—N4ⁱⁱ	2.171 (2)	C6—H6	0.93
Ni2—N4	2.171 (2)	C7—C8	1.372 (4)
S1—C17	1.629 (3)	C7—H7	0.93
S2—C18	1.630 (3)	C8—H8	0.93
N1—C1	1.473 (3)	C9—C10	1.511 (4)
N1—H1A	0.90	C9—H9A	0.97
N1—H1B	0.90	C9—H9B	0.97
N2—C3	1.432 (3)	C10—H10A	0.97
N2—C2	1.479 (3)	C10—H10B	0.97
N2—H2	0.898 (10)	C11—C12	1.387 (3)
N3—C9	1.479 (3)	C11—C16	1.388 (4)
N3—H3A	0.90	C12—C13	1.386 (4)
N3—H3B	0.90	C12—H12	0.93
N4—C11	1.426 (3)	C13—C14	1.374 (4)
N4—C10	1.475 (3)	C13—H13	0.93
N4—H4A	0.889 (10)	C14—C15	1.386 (4)
N5—C17	1.158 (3)	C14—H14	0.93
N6—C18	1.158 (3)	C15—C16	1.383 (4)
C1—C2	1.508 (3)	C15—H15	0.93
C1—H1C	0.97	C16—H16	0.93

N5—Ni1—N5ⁱ	180	N1—C1—H1D	109.9
N5—Ni1—N1ⁱ	90.87 (9)	C2—C1—H1D	109.9
N5ⁱ—Ni1—N1ⁱ	89.13 (9)	H1C—C1—H1D	108.3
N5—Ni1—N1	89.13 (9)	N2—C2—C1	107.7 (2)
N5ⁱ—Ni1—N1	90.87 (9)	N2—C2—H2A	110.2
N1ⁱ—Ni1—N1	180	C1—C2—H2A	110.2
N5—Ni1—N2ⁱ	90.77 (8)	N2—C2—H2B	110.2
N5ⁱ—Ni1—N2ⁱ	89.23 (8)	C1—C2—H2B	110.2
N1ⁱ—Ni1—N2ⁱ	82.40 (8)	H2A—C2—H2B	108.5
N1—Ni1—N2ⁱ	97.60 (8)	C4—C3—C8	119.0 (2)
N5—Ni1—N2	89.23 (8)	C4—C3—N2	122.6 (2)
N5ⁱ—Ni1—N2	90.77 (8)	C8—C3—N2	118.3 (2)
N1ⁱ—Ni1—N2	97.60 (8)	C5—C4—C3	119.6 (3)
N1—Ni1—N2	82.40 (8)	C5—C4—H4	120.2
N2ⁱ—Ni1—N2	180	C3—C4—H4	120.2
N6ⁱⁱ—Ni2—N6	180	C6—C5—C4	121.3 (3)
N6ⁱⁱ—Ni2—N3ⁱⁱ	89.13 (9)	C6—C5—H5	119.3
N6—Ni2—N3ⁱⁱ	90.87 (9)	C4—C5—H5	119.3
N6ⁱⁱ—Ni2—N3	90.87 (9)	C5—C6—C7	118.8 (3)
N6—Ni2—N3	89.13 (9)	C5—C6—H6	120.6
N3ⁱⁱ—Ni2—N3	180	C7—C6—H6	120.6
N6ⁱⁱ—Ni2—N4ⁱⁱ	89.54 (8)	C8—C7—C6	120.6 (3)
N6—Ni2—N4ⁱⁱ	90.46 (8)	C8—C7—H7	119.7
N3ⁱⁱ—Ni2—N4ⁱⁱ	81.54 (8)	C6—C7—H7	119.7
N3—Ni2—N4ⁱⁱ	98.46 (8)	C7—C8—C3	120.6 (3)
N6ⁱⁱ—Ni2—N4	90.46 (8)	C7—C8—H8	119.7
N6—Ni2—N4	89.54 (8)	C3—C8—H8	119.7
N3ⁱⁱ—Ni2—N4	98.46 (8)	N3—C9—C10	108.3 (2)
N3—Ni2—N4	81.54 (8)	N3—C9—H9A	110.0
N4ⁱⁱ—Ni2—N4	180	C10—C9—H9A	110.0
C1—N1—Ni1	108.38 (16)	N3—C9—H9B	110.0
C1—N1—H1A	110.0	C10—C9—H9B	110.0
Ni1—N1—H1A	110.0	H9A—C9—H9B	108.4
C1—N1—H1B	110.0	N4—C10—C9	107.8 (2)
Ni1—N1—H1B	110.0	N4—C10—H10A	110.1
H1A—N1—H1B	108.4	C9—C10—H10A	110.1
C3—N2—C2	117.70 (19)	N4—C10—H10B	110.1
C3—N2—Ni1	116.59 (15)	C9—C10—H10B	110.1
C2—N2—Ni1	104.74 (15)	H10A—C10—H10B	108.5
C3—N2—H2	107 (2)	C12—C11—C16	118.8 (2)
C2—N2—H2	107 (2)	C12—C11—N4	122.6 (2)
Ni1—N2—H2	103 (2)	C16—C11—N4	118.2 (2)
C9—N3—Ni2	109.24 (16)	C13—C12—C11	119.9 (3)
C9—N3—H3A	109.8	C13—C12—H12	120.1
Ni2—N3—H3A	109.8	C11—C12—H12	120.1
C9—N3—H3B	109.8	C14—C13—C12	121.2 (3)
Ni2—N3—H3B	109.8	C14—C13—H13	119.4
H3A—N3—H3B	108.3	C12—C13—H13	119.4
C11—N4—C10	118.3 (2)	C13—C14—C15	119.2 (3)
C11—N4—Ni2	114.31 (16)	C13—C14—H14	120.4
C10—N4—Ni2	105.40 (16)	C15—C14—H14	120.4
C11—N4—H4A	108 (2)	C16—C15—C14	120.0 (3)
C10—N4—H4A	105 (2)	C16—C15—H15	120.0
Ni2—N4—H4A	104 (2)	C14—C15—H15	120.0
C17—N5—Ni1	156.7 (2)	C15—C16—C11	120.9 (3)
C18—N6—Ni2	165.9 (2)	C15—C16—H16	119.6
N1—C1—C2	108.8 (2)	C11—C16—H16	119.6
N1—C1—H1C	109.9	N5—C17—S1	178.3 (3)
C2—C1—H1C	109.9	N6—C18—S2	178.0 (2)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4A···S1ⁱⁱⁱ	0.89 (1)	2.52 (1)	3.393 (2)	168 (3)
N2—H2···S2^iv	0.90 (1)	2.67 (2)	3.436 (2)	144 (3)

Symmetry codes: (iii) x+1, y−1, z; (iv) x−1, y, z.

Experimental details

Crystal data
Chemical formula	[Ni(NCS)₂(C₈H₁₂N₂)₂]
M_r	447.26
Crystal system, space group	Triclinic, P1
Temperature (K)	298
a, b, c (Å)	7.9947 (2), 9.4708 (3), 13.8044 (3)
α, β, γ (°)	93.045 (1), 98.258 (1), 90.934 (1)
V (Å³)	1032.62 (5)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	1.16
Crystal size (mm)	0.18 × 0.17 × 0.17

Data collection
Diffractometer	Bruker SMART CCD area-detector
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.819, 0.828
No. of measured, independent and observed [I > 2σ(I)] reflections	6197, 4314, 3284
R_int	0.018
(sin θ/λ)_max (Å⁻¹)	0.639

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.037, 0.080, 1.03
No. of reflections	4314
No. of parameters	253
No. of restraints	2
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.31, −0.26

Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1998), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Selected bond lengths (Å) top

Ni1—N5	2.073 (2)	Ni2—N6	2.047 (2)
Ni1—N1	2.094 (2)	Ni2—N3	2.104 (2)
Ni1—N2	2.159 (2)	Ni2—N4	2.171 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4A···S1ⁱ	0.89 (1)	2.52 (1)	3.393 (2)	168 (3)
N2—H2···S2ⁱⁱ	0.90 (1)	2.67 (2)	3.436 (2)	144 (3)

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

Acknowledgements

This work was supported by the Natural Science Foundation of China (grant No. 30771696), the Natural Science Foundation of Zhejiang Province (grant No. Y407318) and the Science and Technology Plan of Huzhou (grant No. 2009GG06).

References

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