(1,4-Diaza­cyclo­heptane-κ2N,N′)(2-thioxo-1,3-dithiole-4,5-dithiol­ato-κ2S4,S5)nickel(II)

Wen, Y.-H.; Zhang, Q.-W.

doi:10.1107/S1600536805039632

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(1,4-Diazacycloheptane-κ²N,N′)(2-thioxo-1,3-dithiole-4,5-dithiolato-κ²S⁴,S⁵)nickel(II)

Y.-H. Wen and Q.-W. Zhang

The title complex, [Ni(C₃S₅)(C₅H₁₂N₂)] or [Ni(dmit)(dach)] (dach is 1,4-diazacycloheptane and dmit is 2-thioxo-1,3-dithiole-4,5-dithiolate), crystallizes with two independent molecules per asymmetric unit. In each molecule, the central Ni^II atom is coplanar with the two S atoms of one dmit ligand and two N atoms of one dach ligand. In the crystal structure, some weak S

S interactions and N—H

S and C—H

N hydrogen bonds are present. These interactions generate a three-dimensional framework.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805039632/su6245sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536805039632/su6245Isup2.hkl Contains datablock I

CCDC reference: 296673

checkCIF report

Key indicators

Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.005 Å
R factor = 0.026
wR factor = 0.074
Data-to-parameter ratio = 19.6

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature .        293 K
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Ni1    -   S4      ..       6.54 su
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Ni1    -   S5      ..       6.28 su
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          2
              C8 H12 N2 Ni S5

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   6 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion

Comment top

Over the past decades, transition metal complexes with bis-(dithiolate) ligands, such as dmit, have been widely studied for their semiconducting, conducting, and even superconducting properties (Cassoux et al., 1996). Additionally, diazamesocyclic ligands, such as dach, occupy an important role in coordination chemistry with regard to their manifestation of unique conformations, exceptionally strong ligand fields and their potential for further functionalization (Mills et al., 1990; Musker, 1992; Grapperhaus & Darensbourg, 1998). On combining bis-(dithiolate) and diazamesocyclic ligands as a mixed-ligand system to react with transition metal salts, a series of novel coordination complexes has been obtained. Here, we present the synthesis and crystal structure of the title compound, [Ni(dach)(dmit)], (I).

The molecular structure of complex (I) is illustrated in Fig. 1, and selected bond distances and angles are given in Table 1. The central Ni atom has a square-planar coordination environment, and is surrounded by two S atoms of one dmit ligand, with Ni—S distances of 2.1568 (12) and 2.1584 (10) Å, and two N atoms of a dach ligand, with Ni—N distances of 1.925 (2) and 1.930 (2) Å. The five S of atoms of the dmit ligand are approximately planar. The S₅ planes of the two independent molecules are inclined to one another by ca 85.74°. The independent molecules are linked by N—H···S hydrogen bonds to form a dimer (Table 2).

In the crystal structure of (I) there are some weak S···S interactions [S5···S8ⁱ = 3.5406 (14) Å; symmetry operation: (i) 1 − x, −y, −z]. Symmetry related molecules are also conneced via N—H···S and C—H···S hydrogen bonds [D···A range 3.374 (3)–3.771 (4) Å]. Details are given in Table 2 and Fig. 2.

Experimental top

[TBA][Ni(dmit)₂] and [Ni(DACH)₂](H2O)₄(Ac)₂ were prepared according to the literature procedures (Sun et al., 1996; Guo, 2002; Guo et al., 2001). These two compounds (ratio 1:1) were dissolved separately in acetonitrile at room temperature and allowed to slowly diffuse in an H-shaped tube. After a few weeks, red plate-like crystals, suitable for X-ray diffraction analysis, were obtained.

Computing details top

Data collection: RAPID-AUTO (Rigaku, 1998); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2002); software used to prepare material for publication: SHELXTL.

Figures top

	Fig. 1. A view of the molecule structure of the two independent molecules of complex (I), showing the atom-labelling scheme, with displacement ellipsoids drawn at the 30% probability level. H atoms have been omitted for clarity.
	Fig. 2. A view along the a axis of the crystal packing of (I). The S···S and CH···S interactions are depicted by dashed lines.

(1,4-Diazacycloheptane-κ²N,N')(2-thioxo-1,3-dithiole-4,5-dithiolato- κ²S⁴,S⁵)nickel(II) top

Crystal data top

[Ni(C₃S₅)(C₅H₁₂N₂)]	Z = 4
M_r = 355.21	F(000) = 728
Triclinic, P1	D_x = 1.791 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.3290 (19) Å	Cell parameters from 2987 reflections
b = 11.997 (2) Å	θ = 1.7–27.4°
c = 13.169 (3) Å	µ = 2.24 mm⁻¹
α = 65.20 (3)°	T = 293 K
β = 82.81 (3)°	Block, red
γ = 80.64 (3)°	0.30 × 0.20 × 0.20 mm
V = 1317.5 (6) Å³

Data collection top

Bruker P4 diffractometer	5887 independent reflections
Radiation source: fine-focus sealed tube	4265 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.020
ω scans	θ_max = 27.4°, θ_min = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −12→12
T_min = 0.590, T_max = 0.639	k = −15→15
9484 measured reflections	l = −17→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)] = 0.027	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.074	H-atom parameters constrained
S = 1.01	w = 1/[σ²(F_o²) + (0.0378P)²] where P = (F_o² + 2F_c²)/3
5887 reflections	(Δ/σ)_max < 0.001
301 parameters	Δρ_max = 0.52 e Å⁻³
4 restraints	Δρ_min = −0.43 e Å⁻³

Crystal data top

[Ni(C₃S₅)(C₅H₁₂N₂)]	γ = 80.64 (3)°
M_r = 355.21	V = 1317.5 (6) Å³
Triclinic, P1	Z = 4
a = 9.3290 (19) Å	Mo Kα radiation
b = 11.997 (2) Å	µ = 2.24 mm⁻¹
c = 13.169 (3) Å	T = 293 K
α = 65.20 (3)°	0.30 × 0.20 × 0.20 mm
β = 82.81 (3)°

Data collection top

Bruker P4 diffractometer	5887 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	4265 reflections with I > 2σ(I)
T_min = 0.590, T_max = 0.639	R_int = 0.020
9484 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.027	4 restraints
wR(F²) = 0.074	H-atom parameters constrained
S = 1.01	Δρ_max = 0.52 e Å⁻³
5887 reflections	Δρ_min = −0.43 e Å⁻³
301 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	0.28221 (4)	0.35966 (3)	0.02695 (3)	0.02540 (9)
Ni2	0.18867 (4)	−0.12528 (3)	0.22792 (3)	0.02956 (10)
S1	0.21954 (9)	0.32388 (8)	0.58366 (7)	0.0470 (2)
S2	0.12592 (8)	0.43815 (7)	0.34988 (6)	0.03972 (18)
S3	0.33703 (9)	0.22243 (7)	0.41434 (6)	0.03761 (18)
S4	0.14265 (8)	0.46469 (7)	0.10773 (6)	0.03833 (18)
S5	0.37647 (8)	0.22801 (6)	0.18001 (6)	0.03326 (17)
S6	0.25533 (12)	−0.10177 (9)	−0.32469 (7)	0.0633 (3)
S7	0.11334 (10)	−0.18811 (8)	−0.09236 (7)	0.0504 (2)
S8	0.32194 (10)	−0.01696 (7)	−0.15685 (6)	0.0429 (2)
S9	0.07658 (9)	−0.20743 (8)	0.14839 (7)	0.0428 (2)
S10	0.31138 (9)	−0.02221 (7)	0.07684 (6)	0.03986 (19)
N1	0.4006 (3)	0.2830 (2)	−0.06304 (19)	0.0301 (5)
H1	0.436 (3)	0.2065 (17)	−0.022 (2)	0.036*
N2	0.2284 (3)	0.4764 (2)	−0.12021 (19)	0.0293 (5)
H2	0.155 (2)	0.530 (2)	−0.122 (2)	0.035*
N3	0.1117 (3)	−0.2232 (2)	0.3770 (2)	0.0355 (6)
H3	0.046 (3)	−0.269 (2)	0.380 (3)	0.043*
N4	0.2711 (3)	−0.0572 (2)	0.3139 (2)	0.0353 (6)
H4	0.301 (3)	0.0167 (18)	0.273 (2)	0.042*
C1	0.2273 (3)	0.3275 (3)	0.4553 (2)	0.0337 (6)
C2	0.1904 (3)	0.3859 (3)	0.2457 (2)	0.0310 (6)
C3	0.2904 (3)	0.2849 (2)	0.2763 (2)	0.0290 (6)
C4	0.5258 (3)	0.3533 (3)	−0.1168 (3)	0.0454 (8)
H4A	0.5964	0.3063	−0.1489	0.055*
H4B	0.5725	0.3644	−0.0604	0.055*
C5	0.4798 (3)	0.4779 (3)	−0.2072 (3)	0.0545 (9)
H5A	0.4570	0.4661	−0.2716	0.065*
H5B	0.5614	0.5258	−0.2301	0.065*
C6	0.3499 (4)	0.5522 (3)	−0.1742 (3)	0.0456 (8)
H6A	0.3787	0.5821	−0.1227	0.055*
H6B	0.3170	0.6234	−0.2404	0.055*
C7	0.2001 (3)	0.4047 (3)	−0.1815 (2)	0.0354 (7)
H7A	0.2148	0.4523	−0.2616	0.042*
H7B	0.1002	0.3863	−0.1652	0.042*
C8	0.3049 (3)	0.2842 (2)	−0.1448 (2)	0.0358 (7)
H8A	0.2502	0.2138	−0.1109	0.043*
H8B	0.3629	0.2788	−0.2094	0.043*
C9	0.2298 (4)	−0.1017 (3)	−0.1974 (3)	0.0426 (8)
C10	0.1541 (3)	−0.1472 (3)	0.0123 (2)	0.0347 (7)
C11	0.2522 (3)	−0.0677 (2)	−0.0181 (2)	0.0312 (6)
C12	0.2316 (4)	−0.3167 (3)	0.4369 (3)	0.0471 (8)
H12A	0.2767	−0.3596	0.3906	0.057*
H12B	0.1915	−0.3772	0.5057	0.057*
C13	0.3455 (4)	−0.2608 (3)	0.4643 (3)	0.0617 (10)
H13A	0.3095	−0.2459	0.5305	0.074*
H13B	0.4308	−0.3218	0.4843	0.074*
C14	0.3929 (4)	−0.1441 (3)	0.3773 (3)	0.0492 (8)
H14A	0.4649	−0.1635	0.3253	0.059*
H14B	0.4390	−0.1040	0.4127	0.059*
C15	0.1477 (4)	−0.0311 (3)	0.3859 (3)	0.0465 (8)
H15A	0.0897	0.0459	0.3431	0.056*
H15B	0.1839	−0.0226	0.4480	0.056*
C16	0.0545 (4)	−0.1369 (3)	0.4304 (3)	0.0455 (8)
H16A	0.0580	−0.1797	0.5111	0.055*
H16B	−0.0460	−0.1050	0.4129	0.055*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ni1	0.02730 (19)	0.02911 (18)	0.02124 (19)	−0.00141 (14)	−0.00280 (14)	−0.01208 (14)
Ni2	0.0347 (2)	0.03321 (19)	0.02305 (19)	−0.01038 (15)	0.00127 (16)	−0.01235 (15)
S1	0.0500 (5)	0.0719 (6)	0.0274 (4)	−0.0115 (4)	−0.0022 (4)	−0.0270 (4)
S2	0.0372 (4)	0.0565 (5)	0.0297 (4)	0.0039 (4)	−0.0032 (3)	−0.0248 (4)
S3	0.0496 (5)	0.0386 (4)	0.0241 (4)	−0.0022 (3)	−0.0086 (3)	−0.0116 (3)
S4	0.0362 (4)	0.0519 (4)	0.0263 (4)	0.0127 (3)	−0.0082 (3)	−0.0202 (3)
S5	0.0449 (4)	0.0293 (3)	0.0256 (4)	0.0024 (3)	−0.0064 (3)	−0.0126 (3)
S6	0.0977 (8)	0.0626 (5)	0.0322 (5)	0.0167 (5)	−0.0190 (5)	−0.0272 (4)
S7	0.0633 (6)	0.0603 (5)	0.0390 (5)	−0.0130 (4)	−0.0122 (4)	−0.0269 (4)
S8	0.0633 (5)	0.0391 (4)	0.0261 (4)	−0.0062 (4)	0.0040 (4)	−0.0150 (3)
S9	0.0438 (5)	0.0592 (5)	0.0339 (4)	−0.0249 (4)	0.0023 (4)	−0.0220 (4)
S10	0.0584 (5)	0.0412 (4)	0.0257 (4)	−0.0233 (4)	0.0067 (4)	−0.0156 (3)
N1	0.0350 (13)	0.0286 (11)	0.0270 (13)	0.0030 (10)	−0.0080 (10)	−0.0126 (10)
N2	0.0303 (13)	0.0305 (12)	0.0288 (13)	0.0041 (10)	−0.0056 (10)	−0.0154 (10)
N3	0.0366 (14)	0.0417 (14)	0.0298 (14)	−0.0141 (11)	0.0031 (11)	−0.0142 (11)
N4	0.0505 (16)	0.0322 (12)	0.0251 (13)	−0.0150 (12)	0.0002 (12)	−0.0105 (10)
C1	0.0359 (16)	0.0467 (16)	0.0242 (15)	−0.0150 (13)	0.0007 (13)	−0.0170 (13)
C2	0.0289 (15)	0.0431 (16)	0.0257 (15)	−0.0065 (13)	0.0001 (12)	−0.0184 (12)
C3	0.0348 (15)	0.0319 (14)	0.0228 (14)	−0.0097 (12)	−0.0039 (12)	−0.0110 (11)
C4	0.0277 (16)	0.059 (2)	0.051 (2)	−0.0027 (15)	0.0026 (15)	−0.0269 (17)
C5	0.0419 (19)	0.055 (2)	0.061 (2)	−0.0231 (17)	0.0170 (18)	−0.0180 (18)
C6	0.059 (2)	0.0310 (15)	0.0429 (19)	−0.0127 (15)	0.0014 (16)	−0.0100 (14)
C7	0.0367 (17)	0.0435 (16)	0.0318 (17)	−0.0035 (13)	−0.0081 (13)	−0.0201 (13)
C8	0.0502 (19)	0.0338 (15)	0.0295 (16)	−0.0066 (13)	−0.0085 (14)	−0.0167 (13)
C9	0.055 (2)	0.0383 (16)	0.0335 (17)	0.0133 (14)	−0.0125 (15)	−0.0179 (14)
C10	0.0408 (17)	0.0400 (15)	0.0273 (16)	−0.0021 (13)	−0.0062 (13)	−0.0176 (13)
C11	0.0416 (17)	0.0293 (13)	0.0216 (14)	0.0000 (12)	−0.0017 (13)	−0.0109 (11)
C12	0.059 (2)	0.0368 (16)	0.0396 (19)	−0.0090 (15)	−0.0056 (17)	−0.0078 (14)
C13	0.061 (2)	0.054 (2)	0.060 (3)	−0.0066 (18)	−0.024 (2)	−0.0078 (18)
C14	0.046 (2)	0.055 (2)	0.048 (2)	−0.0149 (16)	−0.0135 (16)	−0.0155 (17)
C15	0.066 (2)	0.0443 (17)	0.0352 (18)	−0.0050 (16)	0.0027 (17)	−0.0239 (15)
C16	0.0460 (19)	0.0551 (19)	0.0363 (18)	−0.0080 (16)	0.0097 (15)	−0.0223 (15)

Geometric parameters (Å, º) top

Ni1—N2	1.925 (2)	N4—C15	1.477 (4)
Ni1—N1	1.930 (2)	N4—C14	1.482 (4)
Ni1—S5	2.1568 (12)	N4—H4	0.894 (17)
Ni1—S4	2.1584 (10)	C2—C3	1.348 (4)
Ni2—N3	1.933 (2)	C4—C5	1.504 (5)
Ni2—N4	1.933 (2)	C4—H4A	0.9700
Ni2—S10	2.1505 (12)	C4—H4B	0.9700
Ni2—S9	2.1533 (9)	C5—C6	1.514 (4)
S1—C1	1.665 (3)	C5—H5A	0.9700
S2—C1	1.720 (3)	C5—H5B	0.9700
S2—C2	1.741 (3)	C6—H6A	0.9700
S3—C1	1.715 (3)	C6—H6B	0.9700
S3—C3	1.733 (3)	C7—C8	1.533 (4)
S4—C2	1.737 (3)	C7—H7A	0.9700
S5—C3	1.736 (3)	C7—H7B	0.9700
S6—C9	1.664 (3)	C8—H8A	0.9700
S7—C9	1.719 (3)	C8—H8B	0.9700
S7—C10	1.745 (3)	C10—C11	1.333 (4)
S8—C9	1.706 (3)	C12—C13	1.497 (4)
S8—C11	1.741 (3)	C12—H12A	0.9700
S9—C10	1.736 (3)	C12—H12B	0.9700
S10—C11	1.735 (3)	C13—C14	1.482 (4)
N1—C8	1.477 (4)	C13—H13A	0.9700
N1—C4	1.479 (4)	C13—H13B	0.9700
N1—H1	0.879 (16)	C14—H14A	0.9700
N2—C7	1.473 (3)	C14—H14B	0.9700
N2—C6	1.486 (4)	C15—C16	1.523 (4)
N2—H2	0.857 (16)	C15—H15A	0.9700
N3—C16	1.478 (3)	C15—H15B	0.9700
N3—C12	1.484 (4)	C16—H16A	0.9700
N3—H3	0.874 (17)	C16—H16B	0.9700

N2—Ni1—N1	80.11 (10)	C6—C5—H5A	108.5
N2—Ni1—S5	171.07 (7)	C4—C5—H5B	108.5
N1—Ni1—S5	93.09 (8)	C6—C5—H5B	108.5
N2—Ni1—S4	92.66 (7)	H5A—C5—H5B	107.5
N1—Ni1—S4	172.73 (7)	N2—C6—C5	111.3 (2)
S5—Ni1—S4	94.03 (4)	N2—C6—H6A	109.4
N3—Ni2—N4	79.65 (10)	C5—C6—H6A	109.4
N3—Ni2—S10	169.31 (8)	N2—C6—H6B	109.4
N4—Ni2—S10	92.47 (7)	C5—C6—H6B	109.4
N3—Ni2—S9	94.03 (8)	H6A—C6—H6B	108.0
N4—Ni2—S9	173.05 (7)	N2—C7—C8	108.6 (2)
S10—Ni2—S9	94.16 (4)	N2—C7—H7A	110.0
C1—S2—C2	97.49 (13)	C8—C7—H7A	110.0
C1—S3—C3	97.58 (14)	N2—C7—H7B	110.0
C2—S4—Ni1	101.62 (10)	C8—C7—H7B	110.0
C3—S5—Ni1	101.56 (10)	H7A—C7—H7B	108.3
C9—S7—C10	97.60 (15)	N1—C8—C7	108.8 (2)
C9—S8—C11	97.75 (15)	N1—C8—H8A	109.9
C10—S9—Ni2	101.29 (10)	C7—C8—H8A	109.9
C11—S10—Ni2	101.32 (10)	N1—C8—H8B	109.9
C8—N1—C4	113.0 (2)	C7—C8—H8B	109.9
C8—N1—Ni1	106.37 (17)	H8A—C8—H8B	108.3
C4—N1—Ni1	108.62 (17)	S6—C9—S8	122.7 (2)
C8—N1—H1	109.9 (19)	S6—C9—S7	124.4 (2)
C4—N1—H1	107.3 (19)	S8—C9—S7	112.88 (17)
Ni1—N1—H1	111.8 (18)	C11—C10—S9	121.5 (2)
C7—N2—C6	112.8 (2)	C11—C10—S7	115.5 (2)
C7—N2—Ni1	107.25 (16)	S9—C10—S7	122.97 (17)
C6—N2—Ni1	107.91 (19)	C10—C11—S10	121.7 (2)
C7—N2—H2	109.3 (19)	C10—C11—S8	116.2 (2)
C6—N2—H2	103.9 (18)	S10—C11—S8	122.07 (16)
Ni1—N2—H2	115.9 (19)	N3—C12—C13	112.7 (2)
C16—N3—C12	113.1 (3)	N3—C12—H12A	109.1
C16—N3—Ni2	107.10 (17)	C13—C12—H12A	109.1
C12—N3—Ni2	107.68 (18)	N3—C12—H12B	109.1
C16—N3—H3	111.0 (19)	C13—C12—H12B	109.1
C12—N3—H3	102.6 (19)	H12A—C12—H12B	107.8
Ni2—N3—H3	115 (2)	C14—C13—C12	118.0 (3)
C15—N4—C14	113.7 (2)	C14—C13—H13A	107.8
C15—N4—Ni2	104.89 (18)	C12—C13—H13A	107.8
C14—N4—Ni2	110.85 (18)	C14—C13—H13B	107.8
C15—N4—H4	104.1 (18)	C12—C13—H13B	107.8
C14—N4—H4	109.5 (19)	H13A—C13—H13B	107.1
Ni2—N4—H4	113.7 (19)	C13—C14—N4	112.9 (3)
S1—C1—S3	123.74 (19)	C13—C14—H14A	109.0
S1—C1—S2	123.16 (17)	N4—C14—H14A	109.0
S3—C1—S2	113.10 (15)	C13—C14—H14B	109.0
C3—C2—S4	121.2 (2)	N4—C14—H14B	109.0
C3—C2—S2	115.6 (2)	H14A—C14—H14B	107.8
S4—C2—S2	122.94 (17)	N4—C15—C16	109.1 (2)
C2—C3—S3	116.2 (2)	N4—C15—H15A	109.9
C2—C3—S5	121.5 (2)	C16—C15—H15A	109.9
S3—C3—S5	122.10 (16)	N4—C15—H15B	109.9
N1—C4—C5	111.8 (3)	C16—C15—H15B	109.9
N1—C4—H4A	109.3	H15A—C15—H15B	108.3
C5—C4—H4A	109.3	N3—C16—C15	108.4 (2)
N1—C4—H4B	109.3	N3—C16—H16A	110.0
C5—C4—H4B	109.3	C15—C16—H16A	110.0
H4A—C4—H4B	107.9	N3—C16—H16B	110.0
C4—C5—C6	115.0 (3)	C15—C16—H16B	110.0
C4—C5—H5A	108.5	H16A—C16—H16B	108.4

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···S10	0.88 (2)	2.87 (2)	3.527 (3)	133 (2)
N2—H2···S4ⁱ	0.86 (2)	2.75 (2)	3.416 (3)	136 (2)
N3—H3···S1ⁱⁱ	0.87 (3)	2.60 (3)	3.401 (3)	152 (2)
N4—H4···S5	0.89 (2)	2.49 (2)	3.374 (3)	173 (2)
C7—H7B···S9ⁱⁱⁱ	0.97	2.83	3.646 (3)	142
C15—H15B···S6^iv	0.97	2.87	3.771 (4)	155
C16—H16B···S6ⁱⁱⁱ	0.97	2.81	3.669 (4)	148

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

Experimental details

Crystal data
Chemical formula	[Ni(C₃S₅)(C₅H₁₂N₂)]
M_r	355.21
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	9.3290 (19), 11.997 (2), 13.169 (3)
α, β, γ (°)	65.20 (3), 82.81 (3), 80.64 (3)
V (Å³)	1317.5 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	2.24
Crystal size (mm)	0.30 × 0.20 × 0.20

Data collection
Diffractometer	Bruker P4 diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.590, 0.639
No. of measured, independent and observed [I > 2σ(I)] reflections	9484, 5887, 4265
R_int	0.020
(sin θ/λ)_max (Å⁻¹)	0.647

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.027, 0.074, 1.01
No. of reflections	5887
No. of parameters	301
No. of restraints	4
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.52, −0.43

Computer programs: RAPID-AUTO (Rigaku, 1998), RAPID-AUTO, CrystalStructure (Rigaku/MSC, 2002), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 2002), SHELXTL.

Selected geometric parameters (Å, º) top

Ni1—N2	1.925 (2)	Ni2—N3	1.933 (2)
Ni1—N1	1.930 (2)	Ni2—N4	1.933 (2)
Ni1—S5	2.1568 (12)	Ni2—S10	2.1505 (12)
Ni1—S4	2.1584 (10)	Ni2—S9	2.1533 (9)

N2—Ni1—N1	80.11 (10)	N3—Ni2—N4	79.65 (10)
N2—Ni1—S5	171.07 (7)	N3—Ni2—S10	169.31 (8)
N1—Ni1—S5	93.09 (8)	N4—Ni2—S10	92.47 (7)
N2—Ni1—S4	92.66 (7)	N3—Ni2—S9	94.03 (8)
N1—Ni1—S4	172.73 (7)	N4—Ni2—S9	173.05 (7)
S5—Ni1—S4	94.03 (4)	S10—Ni2—S9	94.16 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···S10	0.88 (2)	2.87 (2)	3.527 (3)	133 (2)
N2—H2···S4ⁱ	0.86 (2)	2.752 (19)	3.416 (3)	136 (2)
N3—H3···S1ⁱⁱ	0.87 (3)	2.60 (3)	3.401 (3)	152 (2)
N4—H4···S5	0.89 (2)	2.49 (2)	3.374 (3)	173 (2)
C7—H7B···S9ⁱⁱⁱ	0.97	2.83	3.646 (3)	142
C15—H15B···S6^iv	0.97	2.87	3.771 (4)	155
C16—H16B···S6ⁱⁱⁱ	0.97	2.81	3.669 (4)	148

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

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