Hexakis(1H-imidazole-κN)nickel(II) bis-(3-thienylacetate).

In the title complex, [Ni(C(3)H(4)N(2))(6)](C(6)H(5)O(2)S)(2), the Ni(II) atom displays an octa-hedral coordination geometry, defined by six N atoms from the imidazole ligands. Inter-molecular N-H⋯O hydrogen-bonding inter-actions between the cationic complex and 3-thienylacetate anions form a three-dimensional network architecture. The two 3-thienylacetate anions are disordered, with occupancy ratios of circa 0.774 (1):0.226 (1) and ca 0.753 (5):0.247 (5).

Related literature

For related literature, see: Ng et al. (2001 ▶).

Experimental

Crystal data

[Ni(C3H4N2)6](C6H5O2S)2

M = 749.52

Triclinic,

a = 9.2483 (3) Å

b = 9.8529 (3) Å

c = 19.6365 (6) Å

α = 84.696 (1)°

β = 88.380 (2)°

γ = 80.157 (2)°

V = 1755.30 (9) Å3

Z = 2

Mo Kα radiation

μ = 0.72 mm−1

T = 296 (2) K

0.20 × 0.16 × 0.11 mm

Data collection

Bruker APEXII area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2004 ▶) T min = 0.869, T max = 0.924

13333 measured reflections

7140 independent reflections

5337 reflections with I > 2σ(I)

R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.111

S = 1.06

7140 reflections

480 parameters

38 restraints

H-atom parameters constrained

Δρmax = 0.39 e Å−3

Δρmin = −0.27 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); 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.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808006363/sg2218sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808006363/sg2218Isup2.hkl

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

[Ni(C3H4N2)6](C6H5O2S)2	Z = 2
Mr = 749.52	F000 = 780
Triclinic, P1	Dx = 1.418 Mg m−3
Hall symbol: -P 1	Mo Kα radiation λ = 0.71073 Å
a = 9.2483 (3) Å	Cell parameters from 5680 reflections
b = 9.8529 (3) Å	θ = 1.4–28.0º
c = 19.6365 (6) Å	µ = 0.73 mm−1
α = 84.6960 (10)º	T = 296 (2) K
β = 88.380 (2)º	Block, blue
γ = 80.157 (2)º	0.20 × 0.16 × 0.11 mm
V = 1755.30 (9) Å3

Bruker APEXII area-detector diffractometer	7140 independent reflections
Radiation source: fine-focus sealed tube	5337 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.025
T = 296(2) K	θmax = 26.5º
φ and ω scans	θmin = 1.0º
Absorption correction: multi-scan(SADABS; Sheldrick, 2004)	h = −11→11
Tmin = 0.869, Tmax = 0.925	k = −5→12
13333 measured reflections	l = −24→24

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.040	H-atom parameters constrained
wR(F2) = 0.111	w = 1/[σ2(Fo2) + (0.0423P)2 + 0.8694P] where P = (Fo2 + 2Fc2)/3
S = 1.06	(Δ/σ)max = 0.001
7140 reflections	Δρmax = 0.39 e Å−3
480 parameters	Δρmin = −0.27 e Å−3
38 restraints	Extinction correction: none
Primary atom site location: structure-invariant direct methods

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)
C1	0.4131 (4)	0.4287 (3)	0.66425 (18)	0.0627 (9)
H1	0.3888	0.3694	0.6339	0.075*
C2	0.5286 (3)	0.4973 (3)	0.65584 (14)	0.0484 (7)
C3	0.5372 (4)	0.5773 (4)	0.71015 (18)	0.0681 (9)
H3	0.6112	0.6302	0.7111	0.082*
C5	0.6323 (4)	0.4848 (4)	0.59608 (18)	0.0710 (10)
H5A	0.6163	0.4062	0.5727	0.085*
H5B	0.7315	0.4641	0.6135	0.085*
C6	0.6230 (3)	0.6089 (3)	0.54369 (13)	0.0474 (7)
C8	0.3563 (4)	0.2371 (3)	0.99004 (16)	0.0598 (8)
H8	0.4549	0.2448	0.9920	0.072*
C9	0.2493 (3)	0.3502 (3)	0.96818 (14)	0.0500 (7)
C10	0.1119 (4)	0.3137 (4)	0.97049 (19)	0.0683 (9)
H10	0.0270	0.3748	0.9576	0.082*
C11	0.2791 (4)	0.4927 (3)	0.94645 (14)	0.0559 (8)
H11A	0.1976	0.5421	0.9192	0.067*
H11B	0.3661	0.4849	0.9174	0.067*
C12	0.3015 (3)	0.5780 (3)	1.00487 (13)	0.0427 (6)
C13	0.7099 (3)	1.1011 (3)	0.59500 (13)	0.0444 (6)
H13	0.7758	1.1596	0.5804	0.053*
C14	0.5169 (4)	1.0069 (4)	0.60100 (17)	0.0663 (9)
H14	0.4254	0.9851	0.5928	0.080*
C15	0.6119 (3)	0.9449 (3)	0.64942 (17)	0.0637 (9)
H15	0.5958	0.8722	0.6808	0.076*
C16	0.9193 (3)	0.6510 (3)	0.75680 (15)	0.0517 (7)
H16	0.9882	0.6223	0.7234	0.062*
C17	0.8696 (4)	0.5679 (3)	0.80681 (16)	0.0601 (8)
H17	0.8984	0.4727	0.8145	0.072*
C18	0.7630 (3)	0.7782 (3)	0.81614 (13)	0.0446 (6)
H18	0.7026	0.8539	0.8327	0.053*
C19	1.1837 (3)	0.8033 (3)	0.63842 (14)	0.0460 (7)
H19	1.2480	0.8292	0.6684	0.055*
N6	1.2259 (3)	0.7234 (3)	0.58772 (11)	0.0532 (6)
H6	1.3145	0.6887	0.5772	0.064*
C21	0.9893 (3)	0.7778 (3)	0.58834 (13)	0.0478 (7)
H21	0.8912	0.7835	0.5772	0.057*
C22	0.8396 (3)	1.1189 (3)	0.84289 (14)	0.0485 (7)
H22	0.9326	1.0865	0.8606	0.058*
C23	0.6170 (4)	1.2253 (4)	0.83415 (17)	0.0744 (11)
H23	0.5270	1.2794	0.8429	0.089*
C24	0.6547 (3)	1.1572 (3)	0.77818 (16)	0.0613 (9)
H24	0.5936	1.1560	0.7415	0.074*
C25	1.0829 (3)	1.1481 (3)	0.60810 (14)	0.0462 (6)
H25	1.1209	1.0723	0.5843	0.055*
C26	1.0367 (4)	1.3572 (3)	0.63700 (17)	0.0623 (8)
H26	1.0349	1.4516	0.6382	0.075*
C27	0.9656 (4)	1.2747 (3)	0.68025 (16)	0.0554 (8)
H27	0.9057	1.3040	0.7168	0.066*
C28	1.1230 (3)	0.8441 (3)	0.83343 (13)	0.0452 (6)
H28	1.0629	0.7789	0.8455	0.054*
C29	1.2965 (4)	0.9652 (4)	0.83702 (17)	0.0705 (10)
H29	1.3772	1.0002	0.8507	0.085*
C30	1.2145 (3)	1.0096 (4)	0.78075 (16)	0.0600 (8)
H30	1.2302	1.0813	0.7487	0.072*
N1	0.7348 (2)	1.0039 (2)	0.64586 (10)	0.0367 (5)
N2	0.5794 (3)	1.1062 (2)	0.56680 (11)	0.0480 (6)
H2	0.5425	1.1624	0.5332	0.058*
N3	0.8519 (2)	0.7861 (2)	0.76277 (10)	0.0391 (5)
N4	0.7707 (3)	0.6476 (3)	0.84356 (12)	0.0549 (6)
H4A	0.7214	0.6201	0.8783	0.066*
N5	1.0399 (2)	0.8411 (2)	0.64094 (10)	0.0390 (5)
C20	1.1030 (4)	0.7072 (3)	0.55600 (15)	0.0567 (8)
H20	1.0984	0.6565	0.5187	0.068*
N7	0.9954 (2)	1.1416 (2)	0.66199 (10)	0.0389 (5)
N8	1.1108 (3)	1.2744 (3)	0.59158 (13)	0.0551 (6)
H8A	1.1657	1.2993	0.5583	0.066*
N9	1.1042 (2)	0.9323 (2)	0.77832 (10)	0.0419 (5)
N10	1.2373 (3)	0.8589 (3)	0.86970 (12)	0.0527 (6)
H10A	1.2682	0.8107	0.9068	0.063*
N11	0.7967 (2)	1.0899 (2)	0.78359 (10)	0.0405 (5)
N12	0.7343 (3)	1.2000 (3)	0.87473 (12)	0.0579 (7)
H12	0.7404	1.2305	0.9140	0.069*
Ni1	0.91924 (3)	0.96550 (3)	0.711416 (15)	0.03369 (11)
O1	0.5032 (2)	0.6882 (2)	0.53592 (10)	0.0561 (5)
O2	0.7362 (3)	0.6167 (3)	0.50974 (13)	0.0884 (8)
O3	0.2792 (2)	0.7082 (2)	0.99273 (10)	0.0554 (5)
O4	0.3444 (3)	0.5178 (2)	1.06095 (10)	0.0628 (6)
C4	0.4398 (14)	0.5770 (17)	0.7597 (8)	0.089 (3)	0.774 (12)
H4	0.4352	0.6252	0.7985	0.107*	0.774 (12)
S1	0.3174 (3)	0.4661 (3)	0.73853 (14)	0.0805 (17)	0.774 (12)
C7	0.3090 (15)	0.1157 (12)	1.0081 (8)	0.067 (3)	0.753 (5)
H7	0.3670	0.0318	1.0226	0.080*	0.753 (5)
S2	0.1132 (3)	0.1476 (2)	0.99890 (12)	0.0834 (8)	0.753 (5)
S1'	0.3871 (14)	0.5542 (15)	0.7623 (6)	0.124 (12)	0.226 (12)
C4'	0.324 (3)	0.429 (3)	0.7164 (11)	0.060 (8)	0.226 (12)
H4'	0.2484	0.3778	0.7267	0.072*	0.226 (12)
C7'	0.098 (3)	0.1816 (18)	0.9903 (14)	0.16 (2)	0.247 (5)
H7'	0.0132	0.1426	0.9924	0.193*	0.247 (5)
S2'	0.2812 (15)	0.0985 (12)	1.0115 (8)	0.091 (4)	0.247 (5)

	U11	U22	U33	U12	U13	U23
C1	0.064 (2)	0.055 (2)	0.069 (2)	−0.0105 (16)	−0.0164 (18)	0.0026 (16)
C2	0.0470 (16)	0.0488 (17)	0.0432 (15)	0.0005 (13)	−0.0061 (12)	0.0146 (13)
C3	0.085 (3)	0.063 (2)	0.059 (2)	−0.0222 (18)	−0.0127 (19)	0.0047 (17)
C5	0.065 (2)	0.065 (2)	0.068 (2)	0.0153 (17)	0.0114 (17)	0.0182 (18)
C6	0.0476 (16)	0.0587 (18)	0.0361 (14)	−0.0126 (14)	0.0016 (12)	0.0004 (13)
C8	0.063 (2)	0.059 (2)	0.0593 (19)	−0.0130 (16)	0.0103 (15)	−0.0139 (16)
C9	0.0613 (19)	0.0543 (18)	0.0395 (15)	−0.0195 (15)	0.0042 (13)	−0.0138 (13)
C10	0.066 (2)	0.071 (2)	0.072 (2)	−0.0202 (19)	−0.0022 (18)	−0.0153 (19)
C11	0.077 (2)	0.0567 (19)	0.0371 (15)	−0.0195 (16)	−0.0023 (14)	−0.0053 (13)
C12	0.0457 (15)	0.0502 (17)	0.0345 (14)	−0.0154 (12)	0.0054 (11)	−0.0035 (12)
C13	0.0444 (15)	0.0462 (16)	0.0408 (15)	−0.0085 (12)	−0.0051 (12)	0.0078 (12)
C14	0.0580 (19)	0.069 (2)	0.074 (2)	−0.0256 (17)	−0.0246 (17)	0.0182 (18)
C15	0.061 (2)	0.062 (2)	0.070 (2)	−0.0281 (16)	−0.0207 (16)	0.0278 (17)
C16	0.0685 (19)	0.0358 (15)	0.0474 (16)	−0.0021 (13)	0.0075 (14)	−0.0018 (13)
C17	0.090 (2)	0.0334 (16)	0.0547 (18)	−0.0088 (15)	0.0014 (17)	0.0036 (14)
C18	0.0506 (16)	0.0429 (16)	0.0381 (14)	−0.0062 (12)	0.0021 (12)	0.0033 (12)
C19	0.0461 (16)	0.0480 (16)	0.0391 (14)	0.0020 (12)	0.0026 (12)	0.0020 (12)
N6	0.0540 (15)	0.0539 (15)	0.0418 (13)	0.0140 (12)	0.0104 (11)	0.0011 (11)
C21	0.0533 (17)	0.0492 (17)	0.0400 (15)	−0.0046 (13)	−0.0008 (13)	−0.0071 (13)
C22	0.0545 (17)	0.0491 (17)	0.0415 (15)	−0.0043 (13)	0.0022 (13)	−0.0113 (13)
C23	0.072 (2)	0.081 (3)	0.057 (2)	0.0263 (19)	0.0033 (18)	−0.0153 (18)
C24	0.0593 (19)	0.069 (2)	0.0482 (17)	0.0155 (16)	−0.0044 (14)	−0.0168 (15)
C25	0.0505 (16)	0.0413 (16)	0.0462 (16)	−0.0102 (12)	0.0024 (13)	0.0024 (12)
C26	0.075 (2)	0.0413 (18)	0.074 (2)	−0.0226 (16)	0.0059 (18)	−0.0003 (16)
C27	0.066 (2)	0.0464 (18)	0.0539 (18)	−0.0133 (15)	0.0080 (15)	−0.0028 (14)
C28	0.0494 (16)	0.0452 (16)	0.0384 (14)	−0.0024 (12)	−0.0073 (12)	0.0010 (12)
C29	0.063 (2)	0.097 (3)	0.056 (2)	−0.032 (2)	−0.0206 (16)	0.0054 (19)
C30	0.0579 (19)	0.075 (2)	0.0492 (17)	−0.0245 (17)	−0.0101 (14)	0.0100 (16)
N1	0.0421 (12)	0.0319 (11)	0.0344 (11)	−0.0026 (9)	−0.0028 (9)	0.0007 (9)
N2	0.0514 (14)	0.0482 (14)	0.0413 (12)	−0.0034 (11)	−0.0130 (11)	0.0067 (11)
N3	0.0439 (12)	0.0386 (12)	0.0331 (11)	−0.0054 (9)	−0.0008 (9)	0.0021 (9)
N4	0.0746 (17)	0.0543 (16)	0.0373 (12)	−0.0229 (13)	0.0035 (12)	0.0090 (11)
N5	0.0402 (12)	0.0418 (13)	0.0332 (11)	−0.0036 (9)	0.0021 (9)	−0.0008 (9)
C20	0.076 (2)	0.0509 (18)	0.0393 (15)	0.0030 (15)	0.0036 (15)	−0.0110 (13)
N7	0.0437 (12)	0.0353 (12)	0.0372 (11)	−0.0081 (9)	−0.0018 (9)	0.0016 (9)
N8	0.0532 (15)	0.0600 (17)	0.0530 (15)	−0.0209 (12)	0.0030 (12)	0.0104 (13)
N9	0.0428 (12)	0.0468 (13)	0.0348 (11)	−0.0055 (10)	−0.0040 (9)	−0.0005 (10)
N10	0.0574 (15)	0.0593 (16)	0.0387 (13)	−0.0028 (12)	−0.0140 (11)	0.0014 (11)
N11	0.0475 (13)	0.0378 (12)	0.0344 (11)	−0.0039 (10)	0.0026 (9)	−0.0011 (9)
N12	0.0740 (18)	0.0554 (16)	0.0435 (14)	−0.0027 (13)	0.0027 (13)	−0.0164 (12)
Ni1	0.03781 (18)	0.03297 (18)	0.02871 (17)	−0.00365 (13)	0.00005 (12)	0.00110 (12)
O1	0.0570 (13)	0.0541 (13)	0.0480 (11)	0.0056 (10)	0.0028 (9)	0.0148 (10)
O2	0.0612 (15)	0.118 (2)	0.0812 (17)	−0.0209 (14)	0.0233 (13)	0.0226 (16)
O3	0.0763 (14)	0.0448 (12)	0.0438 (11)	−0.0058 (10)	−0.0097 (10)	−0.0023 (9)
O4	0.1051 (18)	0.0539 (13)	0.0348 (11)	−0.0320 (12)	−0.0040 (11)	0.0037 (9)
C4	0.099 (5)	0.095 (5)	0.071 (5)	−0.018 (4)	−0.002 (4)	−0.001 (4)
S1	0.0613 (11)	0.093 (3)	0.077 (2)	−0.0054 (11)	0.0176 (11)	0.024 (2)
C7	0.069 (4)	0.065 (6)	0.068 (5)	−0.020 (4)	0.014 (3)	−0.008 (4)
S2	0.0988 (18)	0.0813 (11)	0.0849 (12)	−0.0531 (10)	0.0155 (10)	−0.0206 (9)
S1'	0.18 (2)	0.109 (13)	0.056 (4)	0.037 (15)	0.015 (7)	0.012 (5)
C4'	0.069 (15)	0.063 (16)	0.054 (16)	−0.033 (13)	0.005 (11)	0.008 (10)
C7'	0.08 (2)	0.25 (5)	0.12 (2)	0.03 (2)	−0.046 (17)	0.05 (2)
S2'	0.141 (11)	0.072 (4)	0.073 (4)	−0.055 (5)	0.026 (5)	−0.017 (3)

C1—C4'	1.299 (15)	N6—H6	0.8600
C1—C2	1.357 (4)	C21—C20	1.336 (4)
C1—S1	1.721 (4)	C21—N5	1.386 (3)
C1—H1	0.9300	C21—H21	0.9300
C2—C3	1.395 (4)	C22—N11	1.312 (3)
C2—C5	1.495 (4)	C22—N12	1.330 (4)
C3—C4	1.307 (12)	C22—H22	0.9300
C3—S1'	1.735 (9)	C23—N12	1.339 (4)
C3—H3	0.9300	C23—C24	1.347 (4)
C5—C6	1.516 (4)	C23—H23	0.9300
C5—H5A	0.9700	C24—N11	1.368 (4)
C5—H5B	0.9700	C24—H24	0.9300
C6—O2	1.235 (3)	C25—N7	1.318 (3)
C6—O1	1.245 (3)	C25—N8	1.323 (4)
C8—C7	1.356 (12)	C25—H25	0.9300
C8—C9	1.401 (4)	C26—C27	1.355 (4)
C8—S2'	1.651 (10)	C26—N8	1.357 (4)
C8—H8	0.9300	C26—H26	0.9300
C9—C10	1.377 (5)	C27—N7	1.372 (4)
C9—C11	1.498 (4)	C27—H27	0.9300
C10—C7'	1.350 (15)	C28—N9	1.320 (3)
C10—S2	1.677 (4)	C28—N10	1.327 (3)
C10—H10	0.9300	C28—H28	0.9300
C11—C12	1.522 (4)	C29—C30	1.353 (4)
C11—H11A	0.9700	C29—N10	1.364 (4)
C11—H11B	0.9700	C29—H29	0.9300
C12—O4	1.243 (3)	C30—N9	1.377 (4)
C12—O3	1.265 (3)	C30—H30	0.9300
C13—N1	1.315 (3)	N1—Ni1	2.127 (2)
C13—N2	1.334 (3)	N2—H2	0.8600
C13—H13	0.9300	N3—Ni1	2.130 (2)
C14—N2	1.338 (4)	N4—H4A	0.8600
C14—C15	1.344 (4)	N5—Ni1	2.103 (2)
C14—H14	0.9300	C20—H20	0.9300
C15—N1	1.360 (4)	N7—Ni1	2.125 (2)
C15—H15	0.9300	N8—H8A	0.8600
C16—C17	1.342 (4)	N9—Ni1	2.149 (2)
C16—N3	1.384 (3)	N10—H10A	0.8600
C16—H16	0.9300	N11—Ni1	2.133 (2)
C17—N4	1.340 (4)	N12—H12	0.8600
C17—H17	0.9300	C4—S1	1.783 (13)
C18—N3	1.318 (3)	C4—H4	0.9300
C18—N4	1.339 (3)	C7—S2	1.796 (12)
C18—H18	0.9300	C7—H7	0.9300
C19—N5	1.319 (3)	S1'—C4'	1.782 (14)
C19—N6	1.335 (3)	C4'—H4'	0.9300
C19—H19	0.9300	C7'—S2'	1.792 (14)
N6—C20	1.351 (4)	C7'—H7'	0.9300
C4'—C1—C2	126.7 (11)	C27—C26—N8	106.2 (3)
C2—C1—S1	111.0 (3)	C27—C26—H26	126.9
C4'—C1—H1	108.8	N8—C26—H26	126.9
C2—C1—H1	124.5	C26—C27—N7	109.7 (3)
S1—C1—H1	124.5	C26—C27—H27	125.2
C1—C2—C3	111.1 (3)	N7—C27—H27	125.2
C1—C2—C5	123.2 (3)	N9—C28—N10	112.4 (3)
C3—C2—C5	125.7 (3)	N9—C28—H28	123.8
C4—C3—C2	119.1 (7)	N10—C28—H28	123.8
C2—C3—S1'	105.0 (6)	C30—C29—N10	106.4 (3)
C4—C3—H3	120.4	C30—C29—H29	126.8
C2—C3—H3	120.4	N10—C29—H29	126.8
S1'—C3—H3	134.6	C29—C30—N9	109.6 (3)
C2—C5—C6	117.1 (3)	C29—C30—H30	125.2
C2—C5—H5A	108.0	N9—C30—H30	125.2
C6—C5—H5A	108.0	C13—N1—C15	104.1 (2)
C2—C5—H5B	108.0	C13—N1—Ni1	126.26 (18)
C6—C5—H5B	108.0	C15—N1—Ni1	129.40 (18)
H5A—C5—H5B	107.3	C13—N2—C14	106.7 (2)
O2—C6—O1	126.1 (3)	C13—N2—H2	126.7
O2—C6—C5	115.1 (3)	C14—N2—H2	126.7
O1—C6—C5	118.7 (3)	C18—N3—C16	104.6 (2)
C7—C8—C9	116.7 (6)	C18—N3—Ni1	128.34 (18)
C9—C8—S2'	110.8 (6)	C16—N3—Ni1	125.55 (18)
C7—C8—H8	121.6	C18—N4—C17	107.4 (2)
C9—C8—H8	121.6	C18—N4—H4A	126.3
S2'—C8—H8	127.5	C17—N4—H4A	126.3
C10—C9—C8	110.9 (3)	C19—N5—C21	104.2 (2)
C10—C9—C11	124.2 (3)	C19—N5—Ni1	126.72 (18)
C8—C9—C11	124.9 (3)	C21—N5—Ni1	129.02 (18)
C7'—C10—C9	119.1 (12)	C21—C20—N6	107.1 (3)
C9—C10—S2	113.1 (3)	C21—C20—H20	126.5
C7'—C10—H10	117.4	N6—C20—H20	126.5
C9—C10—H10	123.4	C25—N7—C27	104.4 (2)
S2—C10—H10	123.4	C25—N7—Ni1	128.32 (19)
C9—C11—C12	114.9 (2)	C27—N7—Ni1	127.25 (19)
C9—C11—H11A	108.6	C25—N8—C26	107.2 (2)
C12—C11—H11A	108.6	C25—N8—H8A	126.4
C9—C11—H11B	108.6	C26—N8—H8A	126.4
C12—C11—H11B	108.6	C28—N9—C30	104.6 (2)
H11A—C11—H11B	107.5	C28—N9—Ni1	125.81 (19)
O4—C12—O3	123.2 (3)	C30—N9—Ni1	128.84 (19)
O4—C12—C11	119.3 (3)	C28—N10—C29	107.0 (2)
O3—C12—C11	117.4 (2)	C28—N10—H10A	126.5
N1—C13—N2	112.3 (2)	C29—N10—H10A	126.5
N1—C13—H13	123.9	C22—N11—C24	104.6 (2)
N2—C13—H13	123.9	C22—N11—Ni1	128.08 (19)
N2—C14—C15	106.8 (3)	C24—N11—Ni1	127.36 (18)
N2—C14—H14	126.6	C22—N12—C23	107.2 (3)
C15—C14—H14	126.6	C22—N12—H12	126.4
C14—C15—N1	110.2 (3)	C23—N12—H12	126.4
C14—C15—H15	124.9	N5—Ni1—N7	89.81 (8)
N1—C15—H15	124.9	N5—Ni1—N1	90.40 (8)
C17—C16—N3	109.3 (3)	N7—Ni1—N1	89.69 (8)
C17—C16—H16	125.4	N5—Ni1—N3	89.52 (8)
N3—C16—H16	125.4	N7—Ni1—N3	177.57 (8)
N4—C17—C16	107.3 (3)	N1—Ni1—N3	92.65 (8)
N4—C17—H17	126.4	N5—Ni1—N11	179.43 (8)
C16—C17—H17	126.4	N7—Ni1—N11	90.73 (8)
N3—C18—N4	111.5 (3)	N1—Ni1—N11	89.78 (8)
N3—C18—H18	124.3	N3—Ni1—N11	89.93 (8)
N4—C18—H18	124.3	N5—Ni1—N9	90.79 (8)
N5—C19—N6	111.9 (3)	N7—Ni1—N9	89.38 (8)
N5—C19—H19	124.0	N1—Ni1—N9	178.48 (8)
N6—C19—H19	124.0	N3—Ni1—N9	88.30 (8)
C19—N6—C20	107.1 (2)	N11—Ni1—N9	89.04 (8)
C19—N6—H6	126.5	C3—C4—S1	106.7 (10)
C20—N6—H6	126.5	C3—C4—H4	126.7
C20—C21—N5	109.6 (3)	S1—C4—H4	126.7
C20—C21—H21	125.2	C1—S1—C4	92.1 (5)
N5—C21—H21	125.2	C8—C7—S2	107.0 (8)
N11—C22—N12	112.0 (3)	C8—C7—H7	126.5
N11—C22—H22	124.0	S2—C7—H7	126.5
N12—C22—H22	124.0	C10—S2—C7	92.2 (4)
N12—C23—C24	106.7 (3)	C3—S1'—C4'	97.7 (11)
N12—C23—H23	126.6	C1—C4'—S1'	99.2 (15)
C24—C23—H23	126.6	C1—C4'—H4'	130.4
C23—C24—N11	109.5 (3)	S1'—C4'—H4'	130.4
C23—C24—H24	125.2	C10—C7'—S2'	104.2 (16)
N11—C24—H24	125.2	C10—C7'—H7'	127.9
N7—C25—N8	112.5 (3)	S2'—C7'—H7'	127.9
N7—C25—H25	123.7	C8—S2'—C7'	94.9 (11)
N8—C25—H25	123.7

D—H···A	D—H	H···A	D···A	D—H···A
N12—H12···O4i	0.86	2.56	3.124 (3)	124
N12—H12···O3i	0.86	1.97	2.826 (3)	170
N10—H10A···O3ii	0.86	1.88	2.718 (3)	164
N8—H8A···O2iii	0.86	1.81	2.660 (3)	170
N4—H4A···O4iv	0.86	1.89	2.688 (3)	153
N2—H2···O1v	0.86	1.91	2.749 (3)	166
N6—H6···O1ii	0.86	1.90	2.711 (3)	156

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N12—H12⋯O4i	0.86	2.56	3.124 (3)	124
N12—H12⋯O3i	0.86	1.97	2.826 (3)	170
N10—H10A⋯O3ii	0.86	1.88	2.718 (3)	164
N8—H8A⋯O2iii	0.86	1.81	2.660 (3)	170
N4—H4A⋯O4iv	0.86	1.89	2.688 (3)	153
N2—H2⋯O1v	0.86	1.91	2.749 (3)	166
N6—H6⋯O1ii	0.86	1.90	2.711 (3)	156

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