{4-Phenyl-1-[1-(1,3-thia-zol-2-yl)ethyl-idene]-thio-semicarbazidato}{4-phenyl-1-[1-(1,3-thia-zol-2-yl)ethylidene]-thio-semi-carbazide}nickel(II) chloride mono-hydrate.

In the title compound, [Ni(C(12)H(11)N(4)S(2))(C(12)H(12)N(4)S(2))]Cl·H(2)O, the Ni(II) ion is chelated by two 2-acetyl-thia-zole-3-phenyl-thio-semicarbazone ligands, forming a distorted octa-hedral complex. The metal ion is coordinated via the thia-zole nitro-gen, imine nitro-gen and thione sulfur atoms from each thio-semicarbazone ligand, and two coordinating units lie almost perpendicular to each other give dihedral angle = 81.89 (1)°]. One thio-semicarbazone unit is found to bind a chloride anion through two hydrogen bonds, while the other is linked with the disordered crystal water molecule. Two mol-ecules are connected to each other through an inter-molecular N-H⋯S inter-action, forming a centrosymmetric dimer. Dimers are linked into sheets by π-π stacking of two phenyl rings [shortest C⋯C distance = 4.041 (3) Å].

Related literature

For general background to thio­semicarbazones and their metal complexes, see: Haiduc & Silverstru (1990 ▶); Nath et al. (2001 ▶); Padhye & Kauffman (1985 ▶); Pellerito & Nagy (2002 ▶); Ali & Livingstone (1974 ▶); Barros-García et al. (2005 ▶); Campbell (1975 ▶). For related structures, see: Ketcham et al. (2002 ▶); Lima et al. (1999 ▶); Viñuelas-Zahínos et al. (2008 ▶); Saeed et al. (2009 ▶); Venkatraman et al. (2009 ▶).

Experimental

Crystal data

[Ni(C12H11N4S2)(C12H12N4S2)]Cl·H2O

M = 663.92

Triclinic,

a = 8.5983 (15) Å

b = 12.929 (2) Å

c = 13.492 (2) Å

α = 101.710 (8)°

β = 90.168 (8)°

γ = 98.946 (7)°

V = 1449.9 (4) Å3

Z = 2

Mo Kα radiation

μ = 1.08 mm−1

T = 90 K

0.33 × 0.27 × 0.08 mm

Data collection

Nonius KappaCCD diffractometer

Absorption correction: multi-scan (SCALEPACK; Otwinowski & Minor, 1997 ▶) T min = 0.716, T max = 0.918

31053 measured reflections

8823 independent reflections

7120 reflections with I > 2σ(I)

R int = 0.027

Refinement

R[F 2 > 2σ(F 2)] = 0.034

wR(F 2) = 0.081

S = 1.03

8823 reflections

374 parameters

3 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.46 e Å−3

Δρmin = −0.62 e Å−3

Data collection: COLLECT (Nonius 2000 ▶); cell refinement: DENZO and SCALEPACK (Otwinowski & Minor, 1997 ▶); data reduction: DENZO and SCALEPACK; program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810013280/br2143sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810013280/br2143Isup2.hkl

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

[Ni(C12H11N4S2)(C12H12N4S2)]Cl·H2O	Z = 2
Mr = 663.92	F(000) = 684
Triclinic, P1	Dx = 1.521 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.5983 (15) Å	Cell parameters from 8157 reflections
b = 12.929 (2) Å	θ = 2.5–30.5°
c = 13.492 (2) Å	µ = 1.08 mm−1
α = 101.710 (8)°	T = 90 K
β = 90.168 (8)°	Fragment, dark orange-red
γ = 98.946 (7)°	0.33 × 0.27 × 0.08 mm
V = 1449.9 (4) Å3

Nonius KappaCCD diffractometer with an Oxford Cryosystems Cryostream cooler	8823 independent reflections
Radiation source: fine-focus sealed tube	7120 reflections with I > 2σ(I)
graphite	Rint = 0.027
ω and φ scans	θmax = 30.5°, θmin = 2.6°
Absorption correction: multi-scan (SCALEPACK; Otwinowski & Minor, 1997)	h = −11→12
Tmin = 0.716, Tmax = 0.918	k = −18→18
31053 measured reflections	l = −18→19

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)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.081	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ2(Fo2) + (0.0317P)2 + 0.7508P] where P = (Fo2 + 2Fc2)/3
8823 reflections	(Δ/σ)max = 0.001
374 parameters	Δρmax = 0.46 e Å−3
3 restraints	Δρmin = −0.62 e Å−3

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 > 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	Occ. (<1)
Ni1	0.73755 (2)	0.394293 (16)	0.219421 (15)	0.01278 (5)
S1	0.69340 (6)	0.47956 (4)	−0.08422 (3)	0.02390 (10)
S2	0.85983 (5)	0.45716 (3)	0.38207 (3)	0.01606 (8)
S3	0.28921 (6)	0.38933 (4)	0.38582 (5)	0.03629 (13)
S4	0.93712 (5)	0.28513 (3)	0.16410 (3)	0.01845 (9)
N1	0.66738 (17)	0.38969 (11)	0.06858 (10)	0.0168 (3)
N2	0.84148 (16)	0.54131 (10)	0.20123 (10)	0.0145 (3)
N3	0.92388 (16)	0.61821 (11)	0.27600 (10)	0.0160 (3)
N4	1.01213 (17)	0.65179 (11)	0.44242 (10)	0.0168 (3)
H4N	1.009 (2)	0.6270 (17)	0.4923 (16)	0.020*
N5	0.52775 (16)	0.43701 (11)	0.28172 (10)	0.0160 (3)
N6	0.61975 (16)	0.25083 (11)	0.24132 (10)	0.0155 (3)
N7	0.68555 (17)	0.16005 (11)	0.21622 (11)	0.0189 (3)
H7N	0.641 (2)	0.1023 (18)	0.2257 (15)	0.023*
N8	0.89284 (18)	0.07572 (12)	0.17390 (12)	0.0204 (3)
H8N	0.823 (3)	0.0229 (18)	0.1878 (16)	0.024*
C1	0.5889 (2)	0.31759 (14)	−0.01143 (13)	0.0208 (3)
H1	0.5375	0.2487	−0.0053	0.025*
C2	0.5902 (2)	0.35226 (14)	−0.10032 (13)	0.0238 (4)
H2	0.5411	0.3118	−0.1623	0.029*
C3	0.7296 (2)	0.47931 (13)	0.04134 (12)	0.0175 (3)
C4	0.8216 (2)	0.56675 (13)	0.11410 (12)	0.0178 (3)
C5	0.8832 (3)	0.67237 (14)	0.08888 (13)	0.0272 (4)
H5A	0.8206	0.7259	0.1221	0.041*
H5B	0.8759	0.6663	0.0154	0.041*
H5C	0.9935	0.6943	0.1126	0.041*
C6	0.93577 (18)	0.58278 (12)	0.36129 (12)	0.0142 (3)
C7	1.0919 (2)	0.75756 (13)	0.45124 (12)	0.0184 (3)
C8	1.1888 (3)	0.78887 (16)	0.37662 (15)	0.0314 (4)
H8	1.1962	0.7405	0.3142	0.038*
C9	1.2748 (3)	0.89174 (17)	0.39429 (16)	0.0383 (5)
H9	1.3432	0.9129	0.3443	0.046*
C10	1.2617 (3)	0.96389 (17)	0.48438 (16)	0.0390 (5)
H10	1.3183	1.0347	0.4952	0.047*
C11	1.1656 (3)	0.93179 (18)	0.55803 (16)	0.0430 (6)
H11	1.1561	0.9806	0.6198	0.052*
C12	1.0830 (3)	0.82842 (16)	0.54207 (14)	0.0334 (5)
H12	1.0199	0.8061	0.5939	0.040*
C13	0.4732 (2)	0.53104 (14)	0.32056 (13)	0.0203 (3)
H13	0.5221	0.5984	0.3088	0.024*
C14	0.3436 (2)	0.51963 (16)	0.37710 (15)	0.0288 (4)
H14	0.2905	0.5765	0.4077	0.035*
C15	0.44159 (19)	0.35541 (14)	0.31114 (13)	0.0188 (3)
C16	0.4887 (2)	0.24947 (13)	0.28841 (13)	0.0195 (3)
C17	0.3995 (2)	0.15581 (15)	0.32400 (18)	0.0336 (5)
H17A	0.3441	0.1050	0.2661	0.050*
H17B	0.3228	0.1804	0.3733	0.050*
H17C	0.4731	0.1206	0.3559	0.050*
C18	0.83731 (19)	0.16880 (13)	0.18405 (12)	0.0167 (3)
C19	1.0377 (2)	0.04743 (14)	0.13910 (13)	0.0198 (3)
C20	1.1345 (2)	0.09939 (15)	0.07580 (14)	0.0236 (4)
H20	1.1079	0.1613	0.0564	0.028*
C21	1.2697 (2)	0.06037 (15)	0.04129 (15)	0.0265 (4)
H21	1.3359	0.0961	−0.0017	0.032*
C22	1.3101 (2)	−0.03042 (15)	0.06854 (15)	0.0274 (4)
H22	1.4035	−0.0564	0.0447	0.033*
C23	1.2126 (2)	−0.08261 (15)	0.13097 (15)	0.0263 (4)
H23	1.2389	−0.1450	0.1495	0.032*
C24	1.0774 (2)	−0.04432 (14)	0.16631 (14)	0.0226 (4)
H24	1.0113	−0.0803	0.2091	0.027*
Cl1	0.61127 (5)	−0.09146 (3)	0.21252 (3)	0.02521 (9)
O1	0.6845 (2)	0.76617 (14)	0.36670 (17)	0.0455 (6)	0.913 (4)
H01	0.662 (3)	0.804 (2)	0.326 (2)	0.068*
H02	0.768 (3)	0.754 (2)	0.342 (2)	0.068*
O1A	0.524 (2)	0.2403 (15)	0.5062 (14)	0.041 (6)*	0.087 (4)

	U11	U22	U33	U12	U13	U23
Ni1	0.01436 (10)	0.01070 (9)	0.01427 (10)	0.00209 (7)	0.00101 (7)	0.00476 (7)
S1	0.0373 (3)	0.0193 (2)	0.01466 (19)	0.00106 (18)	−0.00456 (17)	0.00520 (15)
S2	0.01935 (19)	0.01415 (18)	0.01562 (18)	0.00036 (14)	−0.00207 (14)	0.00703 (14)
S3	0.0315 (3)	0.0256 (2)	0.0568 (3)	0.0120 (2)	0.0271 (2)	0.0142 (2)
S4	0.01769 (19)	0.01322 (18)	0.0258 (2)	0.00322 (14)	0.00702 (16)	0.00654 (15)
N1	0.0201 (7)	0.0132 (6)	0.0174 (6)	0.0027 (5)	−0.0008 (5)	0.0038 (5)
N2	0.0172 (6)	0.0116 (6)	0.0148 (6)	0.0013 (5)	0.0011 (5)	0.0036 (5)
N3	0.0205 (7)	0.0120 (6)	0.0152 (6)	−0.0004 (5)	−0.0020 (5)	0.0041 (5)
N4	0.0221 (7)	0.0147 (6)	0.0137 (6)	−0.0005 (5)	−0.0008 (5)	0.0057 (5)
N5	0.0164 (6)	0.0161 (6)	0.0164 (6)	0.0045 (5)	−0.0003 (5)	0.0037 (5)
N6	0.0161 (6)	0.0122 (6)	0.0185 (6)	0.0030 (5)	0.0004 (5)	0.0034 (5)
N7	0.0192 (7)	0.0099 (6)	0.0288 (8)	0.0025 (5)	0.0060 (6)	0.0066 (6)
N8	0.0206 (7)	0.0138 (7)	0.0296 (8)	0.0055 (5)	0.0081 (6)	0.0089 (6)
C1	0.0238 (8)	0.0153 (8)	0.0220 (8)	0.0027 (6)	−0.0033 (7)	0.0013 (6)
C2	0.0317 (10)	0.0181 (8)	0.0196 (8)	0.0028 (7)	−0.0055 (7)	0.0004 (6)
C3	0.0230 (8)	0.0164 (8)	0.0141 (7)	0.0035 (6)	−0.0002 (6)	0.0052 (6)
C4	0.0238 (8)	0.0146 (7)	0.0157 (7)	0.0006 (6)	0.0000 (6)	0.0069 (6)
C5	0.0435 (11)	0.0185 (8)	0.0185 (8)	−0.0065 (8)	−0.0041 (8)	0.0098 (7)
C6	0.0140 (7)	0.0135 (7)	0.0163 (7)	0.0035 (6)	0.0009 (6)	0.0045 (6)
C7	0.0214 (8)	0.0161 (8)	0.0170 (7)	−0.0011 (6)	−0.0034 (6)	0.0049 (6)
C8	0.0393 (11)	0.0248 (10)	0.0256 (9)	−0.0047 (8)	0.0090 (8)	0.0024 (8)
C9	0.0487 (13)	0.0307 (11)	0.0298 (10)	−0.0144 (10)	0.0076 (9)	0.0085 (8)
C10	0.0541 (14)	0.0257 (10)	0.0294 (10)	−0.0187 (10)	−0.0043 (10)	0.0067 (8)
C11	0.0641 (16)	0.0277 (11)	0.0253 (10)	−0.0162 (10)	0.0042 (10)	−0.0047 (8)
C12	0.0462 (12)	0.0261 (10)	0.0209 (9)	−0.0108 (9)	0.0075 (8)	0.0013 (7)
C13	0.0239 (8)	0.0179 (8)	0.0212 (8)	0.0076 (7)	0.0003 (7)	0.0056 (6)
C14	0.0314 (10)	0.0230 (9)	0.0362 (10)	0.0145 (8)	0.0110 (8)	0.0083 (8)
C15	0.0155 (7)	0.0190 (8)	0.0227 (8)	0.0042 (6)	0.0041 (6)	0.0052 (6)
C16	0.0164 (8)	0.0166 (8)	0.0262 (8)	0.0020 (6)	0.0045 (6)	0.0066 (6)
C17	0.0293 (10)	0.0198 (9)	0.0539 (13)	0.0035 (8)	0.0218 (9)	0.0127 (9)
C18	0.0183 (8)	0.0149 (7)	0.0176 (7)	0.0033 (6)	0.0026 (6)	0.0045 (6)
C19	0.0184 (8)	0.0161 (8)	0.0256 (8)	0.0051 (6)	0.0042 (6)	0.0043 (6)
C20	0.0269 (9)	0.0202 (8)	0.0267 (9)	0.0087 (7)	0.0084 (7)	0.0082 (7)
C21	0.0252 (9)	0.0227 (9)	0.0339 (10)	0.0067 (7)	0.0112 (8)	0.0088 (8)
C22	0.0223 (9)	0.0245 (9)	0.0370 (10)	0.0095 (7)	0.0090 (8)	0.0054 (8)
C23	0.0228 (9)	0.0195 (8)	0.0395 (11)	0.0076 (7)	0.0047 (8)	0.0099 (8)
C24	0.0227 (8)	0.0155 (8)	0.0316 (9)	0.0039 (6)	0.0059 (7)	0.0086 (7)
Cl1	0.0259 (2)	0.0181 (2)	0.0311 (2)	−0.00051 (16)	0.00502 (17)	0.00675 (16)
O1	0.0389 (11)	0.0279 (9)	0.0777 (15)	0.0110 (8)	0.0042 (10)	0.0253 (9)

Ni1—N2	2.0332 (13)	C5—H5B	0.9800
Ni1—N6	2.0479 (14)	C5—H5C	0.9800
Ni1—N5	2.0967 (14)	C7—C12	1.383 (3)
Ni1—N1	2.1076 (14)	C7—C8	1.392 (3)
Ni1—S2	2.3619 (5)	C8—C9	1.392 (3)
Ni1—S4	2.4139 (5)	C8—H8	0.9500
S1—C2	1.7155 (19)	C9—C10	1.391 (3)
S1—C3	1.7223 (16)	C9—H9	0.9500
S2—C6	1.7317 (16)	C10—C11	1.381 (3)
S3—C14	1.705 (2)	C10—H10	0.9500
S3—C15	1.7121 (17)	C11—C12	1.387 (3)
S4—C18	1.6837 (17)	C11—H11	0.9500
N1—C3	1.321 (2)	C12—H12	0.9500
N1—C1	1.372 (2)	C13—C14	1.358 (3)
N2—C4	1.301 (2)	C13—H13	0.9500
N2—N3	1.3703 (18)	C14—H14	0.9500
N3—C6	1.331 (2)	C15—C16	1.462 (2)
N4—C6	1.357 (2)	C16—C17	1.495 (2)
N4—C7	1.413 (2)	C17—H17A	0.9800
N4—H4N	0.80 (2)	C17—H17B	0.9800
N5—C15	1.322 (2)	C17—H17C	0.9800
N5—C13	1.376 (2)	C19—C20	1.391 (2)
N6—C16	1.294 (2)	C19—C24	1.400 (2)
N6—N7	1.3633 (19)	C20—C21	1.383 (2)
N7—C18	1.372 (2)	C20—H20	0.9500
N7—H7N	0.82 (2)	C21—C22	1.391 (3)
N8—C18	1.344 (2)	C21—H21	0.9500
N8—C19	1.408 (2)	C22—C23	1.388 (3)
N8—H8N	0.89 (2)	C22—H22	0.9500
C1—C2	1.362 (2)	C23—C24	1.382 (2)
C1—H1	0.9500	C23—H23	0.9500
C2—H2	0.9500	C24—H24	0.9500
C3—C4	1.461 (2)	O1—H01	0.837 (17)
C4—C5	1.492 (2)	O1—H02	0.819 (17)
C5—H5A	0.9800
N2—Ni1—N6	176.08 (5)	N3—C6—S2	126.98 (12)
N2—Ni1—N5	98.26 (5)	N4—C6—S2	115.26 (11)
N6—Ni1—N5	77.83 (5)	C12—C7—C8	119.82 (17)
N2—Ni1—N1	78.96 (5)	C12—C7—N4	117.41 (15)
N6—Ni1—N1	101.11 (5)	C8—C7—N4	122.49 (16)
N5—Ni1—N1	95.07 (5)	C7—C8—C9	119.35 (18)
N2—Ni1—S2	81.48 (4)	C7—C8—H8	120.3
N6—Ni1—S2	98.44 (4)	C9—C8—H8	120.3
N5—Ni1—S2	88.16 (4)	C10—C9—C8	120.67 (19)
N1—Ni1—S2	160.44 (4)	C10—C9—H9	119.7
N2—Ni1—S4	102.43 (4)	C8—C9—H9	119.7
N6—Ni1—S4	81.48 (4)	C11—C10—C9	119.44 (19)
N5—Ni1—S4	159.14 (4)	C11—C10—H10	120.3
N1—Ni1—S4	91.49 (4)	C9—C10—H10	120.3
S2—Ni1—S4	92.252 (19)	C10—C11—C12	120.2 (2)
C2—S1—C3	89.79 (8)	C10—C11—H11	119.9
C6—S2—Ni1	95.09 (5)	C12—C11—H11	119.9
C14—S3—C15	89.67 (9)	C7—C12—C11	120.49 (18)
C18—S4—Ni1	97.18 (6)	C7—C12—H12	119.8
C3—N1—C1	111.36 (14)	C11—C12—H12	119.8
C3—N1—Ni1	109.88 (11)	C14—C13—N5	114.44 (16)
C1—N1—Ni1	138.41 (12)	C14—C13—H13	122.8
C4—N2—N3	117.28 (13)	N5—C13—H13	122.8
C4—N2—Ni1	117.92 (11)	C13—C14—S3	110.81 (14)
N3—N2—Ni1	124.70 (10)	C13—C14—H14	124.6
C6—N3—N2	111.60 (13)	S3—C14—H14	124.6
C6—N4—C7	130.21 (14)	N5—C15—C16	120.30 (15)
C6—N4—H4N	112.7 (15)	N5—C15—S3	114.19 (13)
C7—N4—H4N	117.1 (15)	C16—C15—S3	125.19 (13)
C15—N5—C13	110.87 (15)	N6—C16—C15	111.47 (15)
C15—N5—Ni1	111.02 (11)	N6—C16—C17	125.99 (16)
C13—N5—Ni1	136.07 (12)	C15—C16—C17	122.37 (15)
C16—N6—N7	120.21 (14)	C16—C17—H17A	109.5
C16—N6—Ni1	118.79 (11)	C16—C17—H17B	109.5
N7—N6—Ni1	120.66 (11)	H17A—C17—H17B	109.5
N6—N7—C18	118.32 (14)	C16—C17—H17C	109.5
N6—N7—H7N	121.7 (15)	H17A—C17—H17C	109.5
C18—N7—H7N	119.6 (15)	H17B—C17—H17C	109.5
C18—N8—C19	130.77 (15)	N8—C18—N7	111.65 (14)
C18—N8—H8N	113.2 (14)	N8—C18—S4	126.23 (13)
C19—N8—H8N	115.9 (14)	N7—C18—S4	122.10 (12)
C2—C1—N1	114.90 (16)	C20—C19—C24	119.69 (16)
C2—C1—H1	122.5	C20—C19—N8	124.65 (15)
N1—C1—H1	122.5	C24—C19—N8	115.51 (15)
C1—C2—S1	110.19 (13)	C21—C20—C19	119.57 (16)
C1—C2—H2	124.9	C21—C20—H20	120.2
S1—C2—H2	124.9	C19—C20—H20	120.2
N1—C3—C4	120.81 (14)	C20—C21—C22	120.99 (17)
N1—C3—S1	113.76 (12)	C20—C21—H21	119.5
C4—C3—S1	125.42 (12)	C22—C21—H21	119.5
N2—C4—C3	112.28 (14)	C23—C22—C21	119.28 (17)
N2—C4—C5	125.17 (15)	C23—C22—H22	120.4
C3—C4—C5	122.55 (14)	C21—C22—H22	120.4
C4—C5—H5A	109.5	C24—C23—C22	120.36 (17)
C4—C5—H5B	109.5	C24—C23—H23	119.8
H5A—C5—H5B	109.5	C22—C23—H23	119.8
C4—C5—H5C	109.5	C23—C24—C19	120.11 (17)
H5A—C5—H5C	109.5	C23—C24—H24	119.9
H5B—C5—H5C	109.5	C19—C24—H24	119.9
N3—C6—N4	117.75 (14)	H01—O1—H02	96 (2)
N6—Ni1—N1—C1	−9.68 (18)	C6—N4—C7—C8	−41.3 (3)
N2—Ni1—N5—C13	−12.01 (16)	Ni1—N5—C15—C16	−6.61 (19)
Ni1—N1—C3—C4	−4.3 (2)	Ni1—N6—C16—C15	4.66 (19)
Ni1—N2—C4—C3	−2.43 (19)	Ni1—N6—N7—C18	5.4 (2)
Ni1—N2—N3—C6	3.64 (18)	N5—C15—C16—N6	1.6 (2)
N1—C3—C4—N2	4.6 (2)	C19—N8—C18—S4	−4.7 (3)
N2—N3—C6—S2	−0.3 (2)	N6—N7—C18—S4	−6.0 (2)
C7—N4—C6—N3	−3.9 (3)	Ni1—S4—C18—N7	3.48 (14)
Ni1—S2—C6—N3	−2.24 (15)	C18—N8—C19—C20	−23.1 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4N···S2i	0.80 (2)	2.54 (2)	3.2595 (15)	150.7 (19)
N7—H7N···Cl1	0.82 (2)	2.45 (2)	3.2050 (15)	153.9 (19)
N8—H8N···Cl1	0.89 (2)	2.23 (2)	3.1051 (16)	168.5 (19)
O1—H01···Cl1ii	0.84 (2)	2.33 (2)	3.1653 (19)	178 (3)
O1—H02···N3	0.82 (2)	2.40 (2)	3.112 (2)	146 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N4—H4N⋯S2i	0.80 (2)	2.54 (2)	3.2595 (15)	150.7 (19)
N7—H7N⋯Cl1	0.82 (2)	2.45 (2)	3.2050 (15)	153.9 (19)
N8—H8N⋯Cl1	0.89 (2)	2.23 (2)	3.1051 (16)	168.5 (19)
O1—H01⋯Cl1ii	0.84 (2)	2.33 (2)	3.1653 (19)	178 (3)
O1—H02⋯N3	0.82 (2)	2.40 (2)	3.112 (2)	146 (3)

Symmetry codes: (i) ; (ii) .