(5,7,7,12,14,14-Hexamethyl-1,4,8,11-tetra-azacyclo-tetra-deca-4,11-diene-κN,N,N,N)(thio-cyanato-κS)nickel(II) perchlorate monohydrate.

In the title compound, [Ni(SCN)(C(16)H(32)N(4))]ClO(4)·H(2)O, the Ni(II) ion is coordinated by the four N atoms of the tetra-azacyclo-tetra-deca-4,11-diene macrocyclic ligand and by the S atom of a thio-cyanate anion. The perchlorate anion is rotationally disordered around one Cl-O bond between two orientations; the occupancies refined to 0.61 (4) and 0.39 (4). Inter-molecular O-H⋯N, N-H⋯O and N-H⋯N hydrogen bonds link two cations, two anions and two solvent water mol-ecules into a centrosymmetric cluster. The crystal packing is further stabilized by weak inter-molecular C-H⋯O hydrogen bonds.

Related literature

For the crystal structures of related complexes, see: Bienko et al. (2007 ▶); Shen et al. (1999 ▶); Szalda & Fujita (1992 ▶).

Experimental

Crystal data

[Ni(NCS)(C16H32N4)]ClO4·H2O

M = 514.71

Triclinic,

a = 7.2678 (11) Å

b = 8.9998 (13) Å

c = 19.513 (2) Å

α = 84.1430 (10)°

β = 87.005 (2)°

γ = 67.3480 (10)°

V = 1171.6 (3) Å3

Z = 2

Mo Kα radiation

μ = 1.07 mm−1

T = 291 K

0.49 × 0.40 × 0.39 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T min = 0.623, T max = 0.681

6103 measured reflections

4062 independent reflections

3247 reflections with I > 2σ(I)

R int = 0.019

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.109

S = 1.03

4062 reflections

299 parameters

H-atom parameters constrained

Δρmax = 0.53 e Å−3

Δρmin = −0.90 e Å−3

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809018091/cv2562sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809018091/cv2562Isup2.hkl

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

[Ni(NCS)(C16H32N4)]ClO4·H2O	Z = 2
Mr = 514.71	F(000) = 544
Triclinic, P1	Dx = 1.459 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.2678 (11) Å	Cell parameters from 2923 reflections
b = 8.9998 (13) Å	θ = 2.5–27.7°
c = 19.513 (2) Å	µ = 1.07 mm−1
α = 84.143 (1)°	T = 291 K
β = 87.005 (2)°	Block, green
γ = 67.348 (1)°	0.49 × 0.40 × 0.39 mm
V = 1171.6 (3) Å3

Bruker SMART CCD area-detector diffractometer	4062 independent reflections
Radiation source: fine-focus sealed tube	3247 reflections with I > 2σ(I)
graphite	Rint = 0.019
φ and ω scans	θmax = 25.0°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −8→8
Tmin = 0.623, Tmax = 0.681	k = −10→8
6103 measured reflections	l = −23→16

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.109	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0501P)2 + 0.9082P] where P = (Fo2 + 2Fc2)/3
4062 reflections	(Δ/σ)max = 0.001
299 parameters	Δρmax = 0.53 e Å−3
0 restraints	Δρmin = −0.89 e Å−3

Experimental. The structure was solved by direct methods (Bruker, 2000) and successive difference Fourier syntheses.

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	Occ. (<1)
Ni1	0.30773 (6)	0.73405 (4)	0.74822 (2)	0.03298 (14)
S1	0.77119 (17)	0.55310 (15)	0.69389 (7)	0.0742 (3)
Cl1	0.83588 (13)	0.23413 (11)	0.87389 (5)	0.0488 (2)
N1	0.3810 (4)	0.8445 (3)	0.81175 (14)	0.0369 (6)
N2	0.3265 (4)	0.5584 (3)	0.81554 (13)	0.0358 (6)
H2	0.4585	0.5040	0.8246	0.043*
N3	0.2600 (4)	0.6153 (3)	0.68168 (14)	0.0370 (6)
N4	0.2731 (4)	0.9145 (3)	0.68173 (13)	0.0358 (6)
H4	0.3769	0.8812	0.6512	0.043*
N5	0.6503 (6)	0.7714 (6)	0.5780 (2)	0.0895 (13)
O1	1.0226 (5)	0.1857 (5)	0.8446 (3)	0.1262 (16)
O2	0.758 (4)	0.401 (3)	0.8792 (15)	0.103 (6)	0.61 (4)
O3	0.698 (3)	0.198 (3)	0.8398 (14)	0.115 (7)	0.61 (4)
O4	0.889 (5)	0.1340 (19)	0.9359 (6)	0.151 (8)	0.61 (4)
O2'	0.765 (6)	0.150 (3)	0.9228 (18)	0.125 (11)	0.39 (4)
O3'	0.724 (6)	0.244 (5)	0.8153 (16)	0.132 (12)	0.39 (4)
O4'	0.774 (7)	0.381 (6)	0.9037 (19)	0.101 (10)	0.39 (4)
O5	0.4522 (5)	0.8714 (5)	0.44382 (19)	0.1003 (11)
H5F	0.5099	0.8396	0.4824	0.120*
H5G	0.4217	0.9727	0.4365	0.120*
C1	0.4568 (6)	0.9196 (5)	0.9214 (2)	0.0567 (10)
H1A	0.5602	0.9470	0.8977	0.085*
H1B	0.5066	0.8575	0.9642	0.085*
H1C	0.3455	1.0168	0.9303	0.085*
C2	0.3917 (5)	0.8227 (4)	0.87771 (17)	0.0393 (7)
C3	0.3413 (5)	0.6913 (4)	0.91705 (18)	0.0470 (8)
H3A	0.2667	0.7355	0.9579	0.056*
H3B	0.4658	0.6070	0.9327	0.056*
C4	0.2248 (5)	0.6103 (4)	0.88317 (17)	0.0423 (8)
C5	0.0098 (5)	0.7264 (5)	0.8714 (2)	0.0587 (10)
H5A	0.0078	0.8222	0.8442	0.088*
H5B	−0.0551	0.7550	0.9150	0.088*
H5C	−0.0589	0.6753	0.8476	0.088*
C6	0.2333 (6)	0.4619 (5)	0.9316 (2)	0.0595 (10)
H6A	0.1473	0.4156	0.9148	0.089*
H6B	0.1902	0.4942	0.9770	0.089*
H6C	0.3676	0.3832	0.9332	0.089*
C7	0.2598 (6)	0.4456 (4)	0.78297 (19)	0.0482 (9)
H7A	0.1158	0.4814	0.7863	0.058*
H7B	0.3180	0.3379	0.8063	0.058*
C8	0.3252 (6)	0.4434 (4)	0.70907 (19)	0.0493 (9)
H8A	0.4689	0.3895	0.7052	0.059*
H8B	0.2635	0.3874	0.6840	0.059*
C9	0.2099 (7)	0.5436 (5)	0.5678 (2)	0.0617 (11)
H9A	0.3387	0.4569	0.5687	0.093*
H9B	0.1862	0.5996	0.5226	0.093*
H9C	0.1092	0.5004	0.5794	0.093*
C10	0.2029 (5)	0.6592 (4)	0.61938 (17)	0.0404 (8)
C11	0.1245 (5)	0.8328 (4)	0.59141 (17)	0.0432 (8)
H11A	0.0002	0.8546	0.5685	0.052*
H11B	0.2179	0.8455	0.5562	0.052*
C12	0.0857 (5)	0.9639 (4)	0.64053 (16)	0.0394 (7)
C13	−0.0909 (5)	0.9766 (4)	0.68875 (18)	0.0466 (8)
H13A	−0.0751	0.8710	0.7093	0.070*
H13B	−0.2121	1.0222	0.6631	0.070*
H13C	−0.0965	1.0448	0.7242	0.070*
C14	0.0433 (6)	1.1253 (4)	0.5974 (2)	0.0554 (10)
H14A	0.0124	1.2101	0.6275	0.083*
H14B	−0.0678	1.1476	0.5680	0.083*
H14C	0.1587	1.1194	0.5698	0.083*
C15	0.2952 (6)	1.0464 (4)	0.71649 (18)	0.0473 (9)
H15A	0.1677	1.1145	0.7353	0.057*
H15B	0.3427	1.1128	0.6838	0.057*
C16	0.4423 (6)	0.9688 (4)	0.77314 (19)	0.0487 (9)
H16A	0.5759	0.9194	0.7542	0.058*
H16B	0.4409	1.0486	0.8032	0.058*
C17	0.7045 (6)	0.6772 (5)	0.6252 (3)	0.0621 (11)

	U11	U22	U33	U12	U13	U23
Ni1	0.0374 (2)	0.0284 (2)	0.0350 (2)	−0.01414 (17)	0.00074 (17)	−0.00531 (16)
S1	0.0542 (6)	0.0768 (8)	0.0868 (9)	−0.0221 (6)	−0.0052 (6)	0.0040 (6)
Cl1	0.0432 (5)	0.0483 (5)	0.0450 (5)	−0.0061 (4)	0.0094 (4)	−0.0117 (4)
N1	0.0370 (14)	0.0317 (14)	0.0435 (16)	−0.0140 (12)	0.0022 (12)	−0.0078 (12)
N2	0.0340 (14)	0.0309 (14)	0.0409 (15)	−0.0111 (11)	−0.0024 (11)	−0.0012 (11)
N3	0.0396 (15)	0.0305 (14)	0.0428 (16)	−0.0149 (12)	0.0008 (12)	−0.0070 (12)
N4	0.0425 (15)	0.0315 (14)	0.0356 (15)	−0.0164 (12)	0.0068 (12)	−0.0078 (11)
N5	0.071 (3)	0.098 (3)	0.082 (3)	−0.017 (2)	0.000 (2)	0.007 (3)
O1	0.070 (2)	0.144 (4)	0.160 (4)	−0.029 (2)	0.041 (2)	−0.062 (3)
O2	0.083 (7)	0.074 (6)	0.143 (16)	−0.012 (5)	−0.027 (11)	−0.026 (10)
O3	0.078 (5)	0.119 (9)	0.169 (19)	−0.053 (6)	−0.008 (9)	−0.040 (11)
O4	0.158 (16)	0.151 (8)	0.071 (5)	0.013 (9)	−0.002 (7)	0.027 (5)
O2'	0.13 (2)	0.110 (13)	0.125 (17)	−0.050 (13)	0.048 (15)	−0.002 (11)
O3'	0.121 (19)	0.15 (2)	0.081 (13)	0.002 (13)	−0.035 (11)	−0.040 (12)
O4'	0.10 (2)	0.10 (2)	0.104 (17)	−0.026 (15)	0.031 (14)	−0.071 (17)
O5	0.106 (3)	0.114 (3)	0.085 (3)	−0.045 (2)	−0.019 (2)	−0.004 (2)
C1	0.063 (2)	0.063 (2)	0.049 (2)	−0.026 (2)	−0.0088 (19)	−0.0173 (19)
C2	0.0320 (16)	0.0397 (18)	0.0408 (19)	−0.0060 (14)	0.0001 (14)	−0.0115 (15)
C3	0.051 (2)	0.052 (2)	0.0383 (19)	−0.0191 (17)	0.0002 (16)	−0.0057 (16)
C4	0.0389 (18)	0.0453 (19)	0.0405 (19)	−0.0151 (15)	0.0031 (15)	0.0002 (15)
C5	0.042 (2)	0.065 (3)	0.061 (3)	−0.0130 (18)	0.0071 (18)	−0.003 (2)
C6	0.063 (2)	0.065 (3)	0.053 (2)	−0.032 (2)	0.0009 (19)	0.0119 (19)
C7	0.058 (2)	0.0326 (18)	0.058 (2)	−0.0216 (17)	−0.0078 (18)	0.0007 (16)
C8	0.063 (2)	0.0290 (17)	0.058 (2)	−0.0171 (16)	−0.0087 (18)	−0.0095 (16)
C9	0.080 (3)	0.054 (2)	0.054 (2)	−0.024 (2)	−0.001 (2)	−0.0235 (19)
C10	0.0436 (19)	0.0434 (19)	0.0402 (19)	−0.0219 (16)	0.0069 (15)	−0.0135 (15)
C11	0.0467 (19)	0.049 (2)	0.0362 (18)	−0.0204 (17)	0.0019 (15)	−0.0068 (15)
C12	0.0427 (18)	0.0382 (18)	0.0333 (17)	−0.0118 (15)	0.0022 (14)	−0.0020 (14)
C13	0.0398 (18)	0.049 (2)	0.044 (2)	−0.0088 (16)	0.0031 (15)	−0.0065 (16)
C14	0.066 (2)	0.044 (2)	0.049 (2)	−0.0161 (19)	−0.0030 (19)	0.0058 (17)
C15	0.067 (2)	0.0337 (18)	0.047 (2)	−0.0252 (17)	0.0034 (17)	−0.0061 (15)
C16	0.061 (2)	0.045 (2)	0.053 (2)	−0.0321 (18)	0.0022 (18)	−0.0107 (17)
C17	0.041 (2)	0.066 (3)	0.075 (3)	−0.015 (2)	0.006 (2)	−0.016 (2)

Ni1—N1	1.880 (3)	C4—C5	1.522 (5)
Ni1—N3	1.888 (3)	C4—C6	1.538 (5)
Ni1—N2	1.916 (2)	C5—H5A	0.9600
Ni1—N4	1.917 (2)	C5—H5B	0.9600
Ni1—S1	3.2979 (13)	C5—H5C	0.9600
S1—C17	1.620 (5)	C6—H6A	0.9600
Cl1—O2'	1.359 (18)	C6—H6B	0.9600
Cl1—O1	1.369 (4)	C6—H6C	0.9600
Cl1—O3	1.385 (18)	C7—C8	1.494 (5)
Cl1—O2	1.40 (3)	C7—H7A	0.9700
Cl1—O4'	1.40 (4)	C7—H7B	0.9700
Cl1—O4	1.408 (11)	C8—H8A	0.9700
Cl1—O3'	1.41 (3)	C8—H8B	0.9700
N1—C2	1.284 (4)	C9—C10	1.505 (5)
N1—C16	1.482 (4)	C9—H9A	0.9600
N2—C7	1.487 (4)	C9—H9B	0.9600
N2—C4	1.505 (4)	C9—H9C	0.9600
N2—H2	0.9100	C10—C11	1.495 (5)
N3—C10	1.278 (4)	C11—C12	1.529 (4)
N3—C8	1.482 (4)	C11—H11A	0.9700
N4—C15	1.489 (4)	C11—H11B	0.9700
N4—C12	1.508 (4)	C12—C13	1.526 (4)
N4—H4	0.9100	C12—C14	1.531 (4)
N5—C17	1.159 (5)	C13—H13A	0.9600
O5—H5F	0.8500	C13—H13B	0.9600
O5—H5G	0.8500	C13—H13C	0.9600
C1—C2	1.491 (5)	C14—H14A	0.9600
C1—H1A	0.9600	C14—H14B	0.9600
C1—H1B	0.9600	C14—H14C	0.9600
C1—H1C	0.9600	C15—C16	1.498 (5)
C2—C3	1.496 (5)	C15—H15A	0.9700
C3—C4	1.523 (5)	C15—H15B	0.9700
C3—H3A	0.9700	C16—H16A	0.9700
C3—H3B	0.9700	C16—H16B	0.9700
N1—Ni1—N3	174.53 (11)	C3—C4—C6	107.2 (3)
N1—Ni1—N2	92.60 (11)	C4—C5—H5A	109.5
N3—Ni1—N2	88.02 (11)	C4—C5—H5B	109.5
N1—Ni1—N4	87.93 (11)	H5A—C5—H5B	109.5
N3—Ni1—N4	91.75 (11)	C4—C5—H5C	109.5
N2—Ni1—N4	176.80 (11)	H5A—C5—H5C	109.5
N1—Ni1—S1	92.86 (8)	H5B—C5—H5C	109.5
N3—Ni1—S1	81.67 (8)	C4—C6—H6A	109.5
N2—Ni1—S1	92.88 (8)	C4—C6—H6B	109.5
N4—Ni1—S1	90.25 (8)	H6A—C6—H6B	109.5
C17—S1—Ni1	85.87 (14)	C4—C6—H6C	109.5
O2'—Cl1—O1	127.9 (17)	H6A—C6—H6C	109.5
O2'—Cl1—O3	75.5 (14)	H6B—C6—H6C	109.5
O1—Cl1—O3	115.2 (10)	N2—C7—C8	108.2 (3)
O2'—Cl1—O2	113.7 (19)	N2—C7—H7A	110.0
O1—Cl1—O2	110.6 (14)	C8—C7—H7A	110.0
O3—Cl1—O2	107.7 (14)	N2—C7—H7B	110.0
O2'—Cl1—O4'	99 (2)	C8—C7—H7B	110.0
O1—Cl1—O4'	115 (2)	H7A—C7—H7B	108.4
O3—Cl1—O4'	119 (2)	N3—C8—C7	105.6 (3)
O2—Cl1—O4'	21 (2)	N3—C8—H8A	110.6
O2'—Cl1—O4	38.1 (9)	C7—C8—H8A	110.6
O1—Cl1—O4	97.2 (13)	N3—C8—H8B	110.6
O3—Cl1—O4	109.6 (11)	C7—C8—H8B	110.6
O2—Cl1—O4	116.7 (11)	H8A—C8—H8B	108.7
O4'—Cl1—O4	96.2 (18)	C10—C9—H9A	109.5
O2'—Cl1—O3'	103.0 (12)	C10—C9—H9B	109.5
O1—Cl1—O3'	99.4 (17)	H9A—C9—H9B	109.5
O3—Cl1—O3'	27.7 (17)	C10—C9—H9C	109.5
O2—Cl1—O3'	94.5 (16)	H9A—C9—H9C	109.5
O4'—Cl1—O3'	113 (2)	H9B—C9—H9C	109.5
O4—Cl1—O3'	136.4 (14)	N3—C10—C11	122.0 (3)
C2—N1—C16	120.5 (3)	N3—C10—C9	123.9 (3)
C2—N1—Ni1	130.8 (2)	C11—C10—C9	114.1 (3)
C16—N1—Ni1	108.6 (2)	C10—C11—C12	119.3 (3)
C7—N2—C4	114.5 (3)	C10—C11—H11A	107.5
C7—N2—Ni1	107.9 (2)	C12—C11—H11A	107.5
C4—N2—Ni1	114.08 (19)	C10—C11—H11B	107.5
C7—N2—H2	106.6	C12—C11—H11B	107.5
C4—N2—H2	106.6	H11A—C11—H11B	107.0
Ni1—N2—H2	106.6	N4—C12—C13	109.9 (3)
C10—N3—C8	120.7 (3)	N4—C12—C11	106.1 (3)
C10—N3—Ni1	129.9 (2)	C13—C12—C11	111.4 (3)
C8—N3—Ni1	109.0 (2)	N4—C12—C14	111.4 (3)
C15—N4—C12	115.1 (2)	C13—C12—C14	109.8 (3)
C15—N4—Ni1	109.0 (2)	C11—C12—C14	108.3 (3)
C12—N4—Ni1	112.87 (18)	C12—C13—H13A	109.5
C15—N4—H4	106.4	C12—C13—H13B	109.5
C12—N4—H4	106.4	H13A—C13—H13B	109.5
Ni1—N4—H4	106.4	C12—C13—H13C	109.5
H5F—O5—H5G	108.3	H13A—C13—H13C	109.5
C2—C1—H1A	109.5	H13B—C13—H13C	109.5
C2—C1—H1B	109.5	C12—C14—H14A	109.5
H1A—C1—H1B	109.5	C12—C14—H14B	109.5
C2—C1—H1C	109.5	H14A—C14—H14B	109.5
H1A—C1—H1C	109.5	C12—C14—H14C	109.5
H1B—C1—H1C	109.5	H14A—C14—H14C	109.5
N1—C2—C1	124.5 (3)	H14B—C14—H14C	109.5
N1—C2—C3	121.1 (3)	N4—C15—C16	107.5 (3)
C1—C2—C3	114.4 (3)	N4—C15—H15A	110.2
C2—C3—C4	120.4 (3)	C16—C15—H15A	110.2
C2—C3—H3A	107.2	N4—C15—H15B	110.2
C4—C3—H3A	107.2	C16—C15—H15B	110.2
C2—C3—H3B	107.2	H15A—C15—H15B	108.5
C4—C3—H3B	107.2	N1—C16—C15	106.6 (3)
H3A—C3—H3B	106.9	N1—C16—H16A	110.4
N2—C4—C5	110.3 (3)	C15—C16—H16A	110.4
N2—C4—C3	107.6 (3)	N1—C16—H16B	110.4
C5—C4—C3	110.8 (3)	C15—C16—H16B	110.4
N2—C4—C6	110.3 (3)	H16A—C16—H16B	108.6
C5—C4—C6	110.7 (3)	N5—C17—S1	176.7 (4)
N1—Ni1—S1—C17	−106.07 (18)	Ni1—N1—C2—C3	−0.1 (5)
N3—Ni1—S1—C17	73.60 (18)	N1—C2—C3—C4	−16.4 (5)
N2—Ni1—S1—C17	161.18 (18)	C1—C2—C3—C4	164.7 (3)
N4—Ni1—S1—C17	−18.13 (18)	C7—N2—C4—C5	−72.0 (3)
N3—Ni1—N1—C2	−110.1 (12)	Ni1—N2—C4—C5	53.0 (3)
N2—Ni1—N1—C2	−13.6 (3)	C7—N2—C4—C3	167.1 (3)
N4—Ni1—N1—C2	163.2 (3)	Ni1—N2—C4—C3	−67.9 (3)
S1—Ni1—N1—C2	−106.7 (3)	C7—N2—C4—C6	50.5 (4)
N3—Ni1—N1—C16	66.7 (12)	Ni1—N2—C4—C6	175.5 (2)
N2—Ni1—N1—C16	163.1 (2)	C2—C3—C4—N2	50.8 (4)
N4—Ni1—N1—C16	−20.1 (2)	C2—C3—C4—C5	−69.8 (4)
S1—Ni1—N1—C16	70.1 (2)	C2—C3—C4—C6	169.4 (3)
N1—Ni1—N2—C7	175.6 (2)	C4—N2—C7—C8	163.6 (3)
N3—Ni1—N2—C7	−9.8 (2)	Ni1—N2—C7—C8	35.4 (3)
N4—Ni1—N2—C7	76 (2)	C10—N3—C8—C7	−145.6 (3)
S1—Ni1—N2—C7	−91.4 (2)	Ni1—N3—C8—C7	41.0 (3)
N1—Ni1—N2—C4	47.2 (2)	N2—C7—C8—N3	−49.6 (4)
N3—Ni1—N2—C4	−138.3 (2)	C8—N3—C10—C11	176.2 (3)
N4—Ni1—N2—C4	−52 (2)	Ni1—N3—C10—C11	−12.0 (5)
S1—Ni1—N2—C4	140.2 (2)	C8—N3—C10—C9	−4.5 (5)
N1—Ni1—N3—C10	−93.8 (12)	Ni1—N3—C10—C9	167.3 (3)
N2—Ni1—N3—C10	169.6 (3)	N3—C10—C11—C12	−8.1 (5)
N4—Ni1—N3—C10	−7.2 (3)	C9—C10—C11—C12	172.5 (3)
S1—Ni1—N3—C10	−97.2 (3)	C15—N4—C12—C13	−78.0 (3)
N1—Ni1—N3—C8	78.7 (12)	Ni1—N4—C12—C13	48.0 (3)
N2—Ni1—N3—C8	−17.9 (2)	C15—N4—C12—C11	161.5 (3)
N4—Ni1—N3—C8	165.3 (2)	Ni1—N4—C12—C11	−72.5 (3)
S1—Ni1—N3—C8	75.3 (2)	C15—N4—C12—C14	43.8 (4)
N1—Ni1—N4—C15	−7.0 (2)	Ni1—N4—C12—C14	169.8 (2)
N3—Ni1—N4—C15	178.5 (2)	C10—C11—C12—N4	50.3 (4)
N2—Ni1—N4—C15	92.6 (19)	C10—C11—C12—C13	−69.3 (4)
S1—Ni1—N4—C15	−99.9 (2)	C10—C11—C12—C14	169.9 (3)
N1—Ni1—N4—C12	−136.2 (2)	C12—N4—C15—C16	160.1 (3)
N3—Ni1—N4—C12	49.2 (2)	Ni1—N4—C15—C16	32.1 (3)
N2—Ni1—N4—C12	−37 (2)	C2—N1—C16—C15	−140.5 (3)
S1—Ni1—N4—C12	130.90 (19)	Ni1—N1—C16—C15	42.3 (3)
C16—N1—C2—C1	2.4 (5)	N4—C15—C16—N1	−48.1 (4)
Ni1—N1—C2—C1	178.8 (2)	Ni1—S1—C17—N5	31 (8)
C16—N1—C2—C3	−176.5 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O2	0.91	2.28	3.16 (3)	162
N4—H4···N5	0.91	2.33	3.241 (5)	175
O5—H5F···N5	0.85	2.09	2.942 (6)	178
O5—H5G···N5i	0.85	2.15	2.997 (6)	178
C3—H3A···O4ii	0.97	2.49	3.450 (16)	172
C3—H3B···O2	0.97	2.48	3.26 (3)	137
C15—H15A···O1iii	0.97	2.37	3.155 (6)	138

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O2	0.91	2.28	3.16 (3)	162
N4—H4⋯N5	0.91	2.33	3.241 (5)	175
O5—H5F⋯N5	0.85	2.09	2.942 (6)	178
O5—H5G⋯N5i	0.85	2.15	2.997 (6)	178
C3—H3A⋯O4ii	0.97	2.49	3.450 (16)	172
C3—H3B⋯O2	0.97	2.48	3.26 (3)	137
C15—H15A⋯O1iii	0.97	2.37	3.155 (6)	138

Symmetry codes: (i) ; (ii) ; (iii) .