Bis{N-ethyl-2-[3-(hy-droxy-imino-κN)butan-2-yl-idene]hydrazinecarbothio-amide-κN,S}nickel(II) dichloride.

In the title complex, [Ni(C(7)H(14)N(4)OS)(2)]Cl(2), the Ni(II) ion is six-coordinated in a distorted octa-hedral geometry by four N atoms from the two imine and two oxime groups, and two S atoms from the thione groups. Two chloride ions complete the asymmetric unit. In the crystal, mol-ecules are linked through N-H⋯Cl and O-H⋯Cl hydrogen bonds into an infinite chain propagating along [101].

Related literature

For bond-length data, see: Allen et al. (1987 ▶). For a related structure, see: Choi et al. (2008 ▶). For the biological activity, pharmacological properties and analytical applications of thio­semicarbazones and their metal complexes, see: Cowley et al. (2002 ▶); Ming (2003 ▶); Lobana et al. (2004 ▶, 2007 ▶).

Experimental

Crystal data

[Ni(C7H14N4OS)2]Cl2

M = 534.17

Monoclinic,

a = 18.4990 (11) Å

b = 14.2097 (9) Å

c = 9.2422 (6) Å

β = 98.542 (1)°

V = 2402.5 (3) Å3

Z = 4

Mo Kα radiation

μ = 1.23 mm−1

T = 293 K

0.42 × 0.20 × 0.12 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.625, T max = 0.869

30693 measured reflections

8190 independent reflections

6071 reflections with I > 2σ(I)

R int = 0.030

Refinement

R[F 2 > 2σ(F 2)] = 0.033

wR(F 2) = 0.089

S = 1.03

8190 reflections

292 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.66 e Å−3

Δρmin = −0.36 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); 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 and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811055383/is5020sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811055383/is5020Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

[Ni(C7H14N4OS)2]Cl2	F(000) = 1112
Mr = 534.17	Dx = 1.477 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 7955 reflections
a = 18.4990 (11) Å	θ = 2.7–31.5°
b = 14.2097 (9) Å	µ = 1.23 mm−1
c = 9.2422 (6) Å	T = 293 K
β = 98.542 (1)°	Block, purple
V = 2402.5 (3) Å3	0.42 × 0.20 × 0.12 mm
Z = 4

Bruker APEXII CCD diffractometer	8190 independent reflections
Radiation source: fine-focus sealed tube	6071 reflections with I > 2σ(I)
graphite	Rint = 0.030
φ and ω scans	θmax = 31.8°, θmin = 2.7°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −27→24
Tmin = 0.625, Tmax = 0.869	k = −21→19
30693 measured reflections	l = −12→13

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)] = 0.033	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.089	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ2(Fo2) + (0.0413P)2 + 0.4822P] where P = (Fo2 + 2Fc2)/3
8190 reflections	(Δ/σ)max = 0.001
292 parameters	Δρmax = 0.66 e Å−3
0 restraints	Δρmin = −0.36 e Å−3

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.

	x	y	z	Uiso*/Ueq
Ni1	0.254705 (10)	0.544056 (14)	0.720936 (19)	0.03000 (6)
S1	0.19095 (2)	0.69236 (3)	0.69747 (5)	0.04214 (10)
S2	0.33886 (2)	0.59247 (4)	0.55926 (4)	0.04259 (11)
O1	0.32326 (8)	0.33683 (10)	0.76904 (16)	0.0528 (3)
O2	0.15128 (7)	0.47332 (11)	0.94881 (14)	0.0493 (3)
N1	0.27241 (7)	0.39758 (10)	0.69614 (14)	0.0355 (3)
N2	0.17389 (7)	0.50408 (10)	0.56264 (13)	0.0318 (3)
N3	0.12478 (8)	0.56856 (10)	0.50132 (15)	0.0376 (3)
N4	0.07395 (8)	0.71317 (11)	0.49656 (17)	0.0422 (3)
N5	0.21534 (7)	0.51429 (10)	0.92075 (14)	0.0345 (3)
N6	0.33784 (7)	0.58110 (9)	0.87569 (13)	0.0322 (3)
N7	0.40248 (8)	0.61137 (11)	0.83749 (15)	0.0405 (3)
N8	0.47653 (9)	0.63277 (13)	0.66593 (19)	0.0510 (4)
C1	0.17121 (8)	0.41842 (12)	0.51582 (16)	0.0351 (3)
C2	0.22784 (9)	0.35631 (12)	0.59529 (17)	0.0373 (3)
C3	0.11569 (11)	0.38175 (14)	0.39472 (19)	0.0484 (4)
H3A	0.1058	0.4288	0.3199	0.073*
H3B	0.0714	0.3668	0.4324	0.073*
H3C	0.1343	0.3261	0.3542	0.073*
C4	0.23136 (14)	0.25422 (14)	0.5599 (3)	0.0642 (6)
H4A	0.2650	0.2233	0.6340	0.096*
H4B	0.2477	0.2468	0.4667	0.096*
H4C	0.1837	0.2268	0.5563	0.096*
C5	0.32848 (9)	0.58058 (12)	1.01105 (16)	0.0363 (3)
C6	0.25807 (9)	0.53975 (12)	1.03697 (16)	0.0360 (3)
C7	0.38261 (11)	0.61688 (17)	1.13467 (19)	0.0564 (5)
H7A	0.4071	0.6708	1.1026	0.085*
H7B	0.4178	0.5687	1.1662	0.085*
H7C	0.3577	0.6344	1.2146	0.085*
C8	0.24030 (12)	0.52761 (18)	1.18843 (19)	0.0585 (6)
H8A	0.1939	0.4968	1.1841	0.088*
H8B	0.2382	0.5882	1.2337	0.088*
H8C	0.2775	0.4901	1.2448	0.088*
C9	0.12641 (8)	0.65727 (11)	0.55863 (16)	0.0336 (3)
C10	0.06787 (12)	0.81258 (14)	0.5282 (2)	0.0518 (5)
H10A	0.1130	0.8444	0.5164	0.062*
H10B	0.0596	0.8208	0.6286	0.062*
C11	0.00570 (14)	0.85451 (17)	0.4263 (3)	0.0682 (6)
H11A	0.0035	0.9210	0.4438	0.102*
H11B	−0.0393	0.8257	0.4429	0.102*
H11C	0.0130	0.8437	0.3270	0.102*
C12	0.41003 (9)	0.61232 (12)	0.69315 (17)	0.0365 (3)
C13	0.49817 (12)	0.64029 (17)	0.5214 (2)	0.0592 (5)
H13A	0.4789	0.6980	0.4747	0.071*
H13B	0.4783	0.5878	0.4612	0.071*
C14	0.58014 (14)	0.64005 (19)	0.5352 (3)	0.0805 (8)
H14A	0.5944	0.6431	0.4395	0.121*
H14B	0.5990	0.5833	0.5831	0.121*
H14C	0.5994	0.6935	0.5916	0.121*
Cl1	0.03036 (3)	0.42615 (5)	0.70489 (5)	0.06167 (15)
Cl2	0.43204 (3)	0.39179 (4)	1.01970 (8)	0.07468 (19)
H1N4	0.0469 (11)	0.6925 (15)	0.440 (2)	0.043 (6)*
H1O2	0.1237 (14)	0.4674 (16)	0.869 (3)	0.063 (7)*
H1N7	0.4416 (12)	0.6072 (15)	0.903 (2)	0.050 (6)*
H1N3	0.0897 (12)	0.5517 (14)	0.456 (2)	0.046 (6)*
H1O1	0.3480 (13)	0.3666 (16)	0.829 (3)	0.055 (7)*
H1N8	0.5085 (13)	0.6376 (15)	0.742 (2)	0.055 (6)*

	U11	U22	U33	U12	U13	U23
Ni1	0.02577 (10)	0.03547 (11)	0.02620 (9)	−0.00196 (8)	−0.00457 (6)	−0.00166 (7)
S1	0.0396 (2)	0.0390 (2)	0.0418 (2)	0.00331 (17)	−0.01353 (16)	−0.00551 (16)
S2	0.0354 (2)	0.0605 (3)	0.03009 (18)	−0.00913 (19)	−0.00085 (14)	0.00010 (17)
O1	0.0535 (8)	0.0468 (8)	0.0519 (7)	0.0120 (6)	−0.0134 (6)	−0.0010 (6)
O2	0.0352 (7)	0.0699 (9)	0.0409 (6)	−0.0168 (6)	−0.0004 (5)	0.0024 (6)
N1	0.0325 (7)	0.0383 (7)	0.0339 (6)	0.0037 (5)	−0.0007 (5)	0.0004 (5)
N2	0.0265 (6)	0.0375 (7)	0.0294 (5)	−0.0032 (5)	−0.0027 (4)	−0.0015 (5)
N3	0.0293 (7)	0.0418 (8)	0.0367 (7)	−0.0015 (6)	−0.0116 (5)	−0.0021 (5)
N4	0.0345 (8)	0.0467 (8)	0.0407 (7)	0.0033 (6)	−0.0094 (6)	0.0010 (6)
N5	0.0284 (6)	0.0406 (7)	0.0329 (6)	−0.0031 (5)	−0.0014 (5)	−0.0009 (5)
N6	0.0267 (6)	0.0373 (7)	0.0301 (6)	−0.0021 (5)	−0.0042 (4)	−0.0001 (5)
N7	0.0287 (7)	0.0552 (9)	0.0345 (6)	−0.0070 (6)	−0.0062 (5)	0.0000 (6)
N8	0.0317 (8)	0.0696 (11)	0.0509 (9)	−0.0086 (7)	0.0035 (6)	0.0000 (8)
C1	0.0299 (8)	0.0434 (9)	0.0310 (7)	−0.0063 (6)	0.0010 (5)	−0.0059 (6)
C2	0.0375 (8)	0.0375 (8)	0.0363 (7)	−0.0027 (7)	0.0037 (6)	−0.0039 (6)
C3	0.0464 (10)	0.0529 (11)	0.0416 (8)	−0.0103 (8)	−0.0073 (7)	−0.0127 (8)
C4	0.0733 (15)	0.0421 (11)	0.0715 (14)	0.0015 (10)	−0.0082 (11)	−0.0138 (10)
C5	0.0341 (8)	0.0420 (9)	0.0293 (6)	−0.0019 (7)	−0.0070 (6)	−0.0018 (6)
C6	0.0366 (8)	0.0408 (8)	0.0287 (6)	−0.0006 (7)	−0.0017 (6)	0.0004 (6)
C7	0.0516 (11)	0.0787 (14)	0.0341 (8)	−0.0182 (10)	−0.0090 (7)	−0.0095 (9)
C8	0.0573 (12)	0.0867 (16)	0.0300 (8)	−0.0173 (11)	0.0020 (7)	0.0016 (9)
C9	0.0272 (7)	0.0411 (8)	0.0306 (6)	−0.0015 (6)	−0.0018 (5)	0.0019 (6)
C10	0.0532 (11)	0.0482 (11)	0.0497 (10)	0.0130 (9)	−0.0064 (8)	0.0007 (8)
C11	0.0692 (15)	0.0600 (13)	0.0677 (13)	0.0232 (11)	−0.0153 (11)	0.0093 (11)
C12	0.0301 (8)	0.0401 (8)	0.0379 (7)	−0.0024 (6)	0.0001 (6)	0.0004 (6)
C13	0.0509 (12)	0.0671 (13)	0.0637 (12)	−0.0074 (10)	0.0218 (10)	0.0040 (10)
C14	0.0590 (15)	0.0699 (16)	0.122 (2)	−0.0031 (12)	0.0435 (15)	−0.0051 (15)
Cl1	0.0405 (3)	0.0975 (4)	0.0438 (2)	−0.0219 (3)	−0.00425 (18)	−0.0083 (2)
Cl2	0.0534 (3)	0.0625 (3)	0.0937 (4)	−0.0016 (3)	−0.0363 (3)	0.0016 (3)

Ni1—N1	2.1247 (14)	C1—C3	1.496 (2)
Ni1—N2	2.0120 (12)	C2—C4	1.491 (3)
Ni1—N5	2.1258 (13)	C3—H3A	0.9600
Ni1—N6	2.0086 (12)	C3—H3B	0.9600
Ni1—S1	2.4089 (5)	C3—H3C	0.9600
Ni1—S2	2.4126 (5)	C4—H4A	0.9600
S1—C9	1.6927 (15)	C4—H4B	0.9600
S2—C12	1.6912 (16)	C4—H4C	0.9600
O1—N1	1.3769 (18)	C5—C6	1.478 (2)
O1—H1O1	0.79 (2)	C5—C7	1.495 (2)
O2—N5	1.3791 (18)	C6—C8	1.495 (2)
O2—H1O2	0.83 (2)	C7—H7A	0.9600
N1—C2	1.290 (2)	C7—H7B	0.9600
N2—C1	1.290 (2)	C7—H7C	0.9600
N2—N3	1.3538 (19)	C8—H8A	0.9600
N3—C9	1.366 (2)	C8—H8B	0.9600
N3—H1N3	0.76 (2)	C8—H8C	0.9600
N4—C9	1.318 (2)	C10—C11	1.497 (3)
N4—C10	1.450 (3)	C10—H10A	0.9700
N4—H1N4	0.73 (2)	C10—H10B	0.9700
N5—C6	1.2873 (19)	C11—H11A	0.9600
N6—C5	1.288 (2)	C11—H11B	0.9600
N6—N7	1.3656 (19)	C11—H11C	0.9600
N7—C12	1.362 (2)	C13—C14	1.503 (3)
N7—H1N7	0.87 (2)	C13—H13A	0.9700
N8—C12	1.324 (2)	C13—H13B	0.9700
N8—C13	1.454 (3)	C14—H14A	0.9600
N8—H1N8	0.85 (2)	C14—H14B	0.9600
C1—C2	1.479 (2)	C14—H14C	0.9600
N6—Ni1—N2	177.98 (5)	C2—C4—H4A	109.5
N6—Ni1—N1	102.68 (5)	C2—C4—H4B	109.5
N2—Ni1—N1	75.81 (5)	H4A—C4—H4B	109.5
N6—Ni1—N5	76.02 (5)	C2—C4—H4C	109.5
N2—Ni1—N5	105.19 (5)	H4A—C4—H4C	109.5
N1—Ni1—N5	88.68 (5)	H4B—C4—H4C	109.5
N6—Ni1—S1	98.49 (4)	N6—C5—C6	114.12 (13)
N2—Ni1—S1	83.14 (4)	N6—C5—C7	124.67 (16)
N1—Ni1—S1	158.21 (4)	C6—C5—C7	121.21 (14)
N5—Ni1—S1	91.49 (4)	N5—C6—C5	114.95 (13)
N6—Ni1—S2	82.53 (4)	N5—C6—C8	123.77 (16)
N2—Ni1—S2	96.22 (4)	C5—C6—C8	121.26 (14)
N1—Ni1—S2	95.08 (4)	C5—C7—H7A	109.5
N5—Ni1—S2	158.53 (4)	C5—C7—H7B	109.5
S1—Ni1—S2	92.701 (19)	H7A—C7—H7B	109.5
C9—S1—Ni1	95.24 (6)	C5—C7—H7C	109.5
C12—S2—Ni1	95.63 (6)	H7A—C7—H7C	109.5
N1—O1—H1O1	107.0 (17)	H7B—C7—H7C	109.5
N5—O2—H1O2	107.9 (17)	C6—C8—H8A	109.5
C2—N1—O1	112.67 (14)	C6—C8—H8B	109.5
C2—N1—Ni1	115.53 (11)	H8A—C8—H8B	109.5
O1—N1—Ni1	131.80 (10)	C6—C8—H8C	109.5
C1—N2—N3	120.53 (13)	H8A—C8—H8C	109.5
C1—N2—Ni1	119.84 (11)	H8B—C8—H8C	109.5
N3—N2—Ni1	119.56 (10)	N4—C9—N3	114.52 (14)
N2—N3—C9	119.17 (12)	N4—C9—S1	122.91 (13)
N2—N3—H1N3	118.9 (16)	N3—C9—S1	122.57 (12)
C9—N3—H1N3	118.3 (16)	N4—C10—C11	109.65 (17)
C9—N4—C10	125.00 (15)	N4—C10—H10A	109.7
C9—N4—H1N4	116.9 (17)	C11—C10—H10A	109.7
C10—N4—H1N4	118.1 (17)	N4—C10—H10B	109.7
C6—N5—O2	113.58 (13)	C11—C10—H10B	109.7
C6—N5—Ni1	114.95 (11)	H10A—C10—H10B	108.2
O2—N5—Ni1	131.47 (10)	C10—C11—H11A	109.5
C5—N6—N7	120.14 (13)	C10—C11—H11B	109.5
C5—N6—Ni1	119.40 (11)	H11A—C11—H11B	109.5
N7—N6—Ni1	120.38 (9)	C10—C11—H11C	109.5
C12—N7—N6	118.52 (13)	H11A—C11—H11C	109.5
C12—N7—H1N7	118.8 (14)	H11B—C11—H11C	109.5
N6—N7—H1N7	118.0 (14)	N8—C12—N7	114.94 (15)
C12—N8—C13	125.52 (17)	N8—C12—S2	122.81 (13)
C12—N8—H1N8	114.4 (15)	N7—C12—S2	122.22 (12)
C13—N8—H1N8	119.9 (15)	N8—C13—C14	109.5 (2)
N2—C1—C2	114.04 (13)	N8—C13—H13A	109.8
N2—C1—C3	124.57 (15)	C14—C13—H13A	109.8
C2—C1—C3	121.38 (15)	N8—C13—H13B	109.8
N1—C2—C1	114.65 (14)	C14—C13—H13B	109.8
N1—C2—C4	123.84 (17)	H13A—C13—H13B	108.2
C1—C2—C4	121.51 (15)	C13—C14—H14A	109.5
C1—C3—H3A	109.5	C13—C14—H14B	109.5
C1—C3—H3B	109.5	H14A—C14—H14B	109.5
H3A—C3—H3B	109.5	C13—C14—H14C	109.5
C1—C3—H3C	109.5	H14A—C14—H14C	109.5
H3A—C3—H3C	109.5	H14B—C14—H14C	109.5
H3B—C3—H3C	109.5
N6—Ni1—S1—C9	176.16 (7)	N1—Ni1—N6—N7	91.00 (12)
N2—Ni1—S1—C9	−2.63 (6)	N5—Ni1—N6—N7	176.39 (13)
N1—Ni1—S1—C9	−17.59 (12)	S1—Ni1—N6—N7	−94.19 (12)
N5—Ni1—S1—C9	−107.75 (6)	S2—Ni1—N6—N7	−2.56 (11)
S2—Ni1—S1—C9	93.31 (6)	C5—N6—N7—C12	−179.00 (16)
N6—Ni1—S2—C12	5.33 (7)	Ni1—N6—N7—C12	−2.5 (2)
N2—Ni1—S2—C12	−173.07 (7)	N3—N2—C1—C2	−179.18 (14)
N1—Ni1—S2—C12	−96.83 (7)	Ni1—N2—C1—C2	4.00 (18)
N5—Ni1—S2—C12	2.54 (13)	N3—N2—C1—C3	−0.5 (2)
S1—Ni1—S2—C12	103.55 (6)	Ni1—N2—C1—C3	−177.35 (13)
N6—Ni1—N1—C2	−176.40 (12)	O1—N1—C2—C1	178.83 (13)
N2—Ni1—N1—C2	2.22 (11)	Ni1—N1—C2—C1	−0.92 (18)
N5—Ni1—N1—C2	108.25 (12)	O1—N1—C2—C4	−0.7 (3)
S1—Ni1—N1—C2	17.54 (19)	Ni1—N1—C2—C4	179.55 (16)
S2—Ni1—N1—C2	−92.93 (12)	N2—C1—C2—N1	−1.9 (2)
N6—Ni1—N1—O1	3.91 (15)	C3—C1—C2—N1	179.44 (15)
N2—Ni1—N1—O1	−177.48 (15)	N2—C1—C2—C4	177.68 (18)
N5—Ni1—N1—O1	−71.44 (15)	C3—C1—C2—C4	−1.0 (3)
S1—Ni1—N1—O1	−162.15 (10)	N7—N6—C5—C6	−175.83 (14)
S2—Ni1—N1—O1	87.38 (14)	Ni1—N6—C5—C6	7.6 (2)
N1—Ni1—N2—C1	−3.45 (12)	N7—N6—C5—C7	3.9 (3)
N5—Ni1—N2—C1	−88.10 (12)	Ni1—N6—C5—C7	−172.64 (15)
S1—Ni1—N2—C1	−177.77 (12)	O2—N5—C6—C5	177.75 (14)
S2—Ni1—N2—C1	90.24 (12)	Ni1—N5—C6—C5	−3.03 (19)
N1—Ni1—N2—N3	179.70 (12)	O2—N5—C6—C8	−0.7 (2)
N5—Ni1—N2—N3	95.05 (12)	Ni1—N5—C6—C8	178.50 (15)
S1—Ni1—N2—N3	5.37 (11)	N6—C5—C6—N5	−2.7 (2)
S2—Ni1—N2—N3	−86.61 (11)	C7—C5—C6—N5	177.58 (17)
C1—N2—N3—C9	176.31 (14)	N6—C5—C6—C8	175.84 (17)
Ni1—N2—N3—C9	−6.9 (2)	C7—C5—C6—C8	−3.9 (3)
N6—Ni1—N5—C6	5.21 (12)	C10—N4—C9—N3	−173.91 (17)
N2—Ni1—N5—C6	−176.46 (12)	C10—N4—C9—S1	5.8 (3)
N1—Ni1—N5—C6	108.63 (12)	N2—N3—C9—N4	−176.40 (14)
S1—Ni1—N5—C6	−93.17 (12)	N2—N3—C9—S1	3.9 (2)
S2—Ni1—N5—C6	8.1 (2)	Ni1—S1—C9—N4	−179.39 (14)
N6—Ni1—N5—O2	−175.74 (15)	Ni1—S1—C9—N3	0.27 (14)
N2—Ni1—N5—O2	2.59 (15)	C9—N4—C10—C11	174.47 (19)
N1—Ni1—N5—O2	−72.32 (14)	C13—N8—C12—N7	−178.54 (19)
S1—Ni1—N5—O2	85.88 (14)	C13—N8—C12—S2	−0.6 (3)
S2—Ni1—N5—O2	−172.89 (10)	N6—N7—C12—N8	−173.06 (16)
N1—Ni1—N6—C5	−92.46 (13)	N6—N7—C12—S2	8.9 (2)
N5—Ni1—N6—C5	−7.07 (12)	Ni1—S2—C12—N8	173.07 (15)
S1—Ni1—N6—C5	82.35 (13)	Ni1—S2—C12—N7	−9.10 (15)
S2—Ni1—N6—C5	173.99 (13)	C12—N8—C13—C14	−165.8 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N4—H1N4···Cl1i	0.730 (19)	2.47 (2)	3.1689 (17)	161 (2)
O2—H1O2···Cl1	0.84 (3)	2.20 (3)	3.0062 (14)	161 (2)
N7—H1N7···Cl2ii	0.87 (2)	2.34 (2)	3.1488 (16)	153.9 (17)
N3—H1N3···Cl1i	0.76 (2)	2.50 (2)	3.2015 (16)	154 (2)
O1—H1O1···Cl2	0.79 (3)	2.20 (3)	2.9396 (16)	157 (2)
N8—H1N8···Cl2ii	0.85 (2)	2.349 (19)	3.1567 (19)	159 (2)

Table 1

Selected bond lengths (Å)

Ni1—N1	2.1247 (14)
Ni1—N2	2.0120 (12)
Ni1—N5	2.1258 (13)
Ni1—N6	2.0086 (12)
Ni1—S1	2.4089 (5)
Ni1—S2	2.4126 (5)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N4—H1N4⋯Cl1i	0.730 (19)	2.47 (2)	3.1689 (17)	161 (2)
O2—H1O2⋯Cl1	0.84 (3)	2.20 (3)	3.0062 (14)	161 (2)
N7—H1N7⋯Cl2ii	0.87 (2)	2.34 (2)	3.1488 (16)	153.9 (17)
N3—H1N3⋯Cl1i	0.76 (2)	2.50 (2)	3.2015 (16)	154 (2)
O1—H1O1⋯Cl2	0.79 (3)	2.20 (3)	2.9396 (16)	157 (2)
N8—H1N8⋯Cl2ii	0.85 (2)	2.349 (19)	3.1567 (19)	159 (2)

Symmetry codes: (i) ; (ii) .