Bis{2-[3-(dimethyl-ammonio)-propyl-imino-methyl-κN]-6-meth-oxy-phenolato-κO}bis-(thio-cyanato-κN)nickel(II).

The asymmetric unit of the title complex, [Ni(NCS)(2)(C(13)H(20)N(2)O(2))(2)], consists of two half-mol-ecules, both of which are completed by crystallographic inversion symmetry (Ni(2+) site symmetry = in both cases). Both metal ions are six-coordinated in distorted trans-NiO(2)N(4) geometries arising from two N,O-bidentate Schiff base ligands and two N-bonded thio-cyanate ions. The mol-ecular conformations are reinforced by two intra-molecular N-H⋯O hydrogen bonds.

Related literature

For related structures and background references, see: Xue et al. (2010a ▶,b ▶).

Experimental

Crystal data

[Ni(NCS)2(C13H20N2O2)2]

M = 647.49

Monoclinic,

a = 16.228 (2) Å

b = 15.642 (2) Å

c = 13.3912 (18) Å

β = 113.132 (2)°

V = 3126.0 (7) Å3

Z = 4

Mo Kα radiation

μ = 0.80 mm−1

T = 298 K

0.23 × 0.23 × 0.20 mm

Data collection

Bruker SMART CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.838, T max = 0.857

17748 measured reflections

6772 independent reflections

4916 reflections with I > 2σ(I)

R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.035

wR(F 2) = 0.091

S = 1.02

6772 reflections

385 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.26 e Å−3

Δρmin = −0.38 e Å−3

Data collection: SMART (Bruker, 1998 ▶); cell refinement: SAINT (Bruker, 1998 ▶); 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 global, I. DOI: 10.1107/S1600536810038298/hb5649sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810038298/hb5649Isup2.hkl

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

[Ni(NCS)2(C13H20N2O2)2]	F(000) = 1368
Mr = 647.49	Dx = 1.376 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5211 reflections
a = 16.228 (2) Å	θ = 2.6–27.2°
b = 15.642 (2) Å	µ = 0.80 mm−1
c = 13.3912 (18) Å	T = 298 K
β = 113.132 (2)°	Block, green
V = 3126.0 (7) Å3	0.23 × 0.23 × 0.20 mm
Z = 4

Bruker SMART CCD diffractometer	6772 independent reflections
Radiation source: fine-focus sealed tube	4916 reflections with I > 2σ(I)
graphite	Rint = 0.026
ω scans	θmax = 27.0°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −18→20
Tmin = 0.838, Tmax = 0.857	k = −19→19
17748 measured reflections	l = −17→7

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)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.091	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ2(Fo2) + (0.0418P)2 + 0.616P] where P = (Fo2 + 2Fc2)/3
6772 reflections	(Δ/σ)max = 0.001
385 parameters	Δρmax = 0.26 e Å−3
2 restraints	Δρmin = −0.38 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	0.5000	0.5000	0.0000	0.03134 (10)
Ni2	0.0000	0.5000	0.0000	0.03281 (10)
S1	0.28158 (5)	0.31526 (5)	−0.26156 (5)	0.0710 (2)
S2	0.18778 (4)	0.75758 (4)	0.05566 (5)	0.05524 (17)
O1	0.48274 (9)	0.43998 (8)	0.12568 (11)	0.0399 (3)
O2	0.54271 (11)	0.39569 (10)	0.33999 (13)	0.0592 (4)
O3	0.01284 (9)	0.51671 (8)	0.15603 (11)	0.0395 (3)
O4	−0.02789 (11)	0.52191 (10)	0.33375 (13)	0.0528 (4)
N1	0.38379 (10)	0.57261 (10)	−0.02589 (13)	0.0341 (4)
N2	0.50658 (12)	0.73003 (11)	−0.11985 (15)	0.0408 (4)
N3	0.41756 (12)	0.41330 (11)	−0.11307 (15)	0.0452 (4)
N4	0.11950 (10)	0.42923 (10)	0.05634 (13)	0.0347 (4)
N5	0.00617 (11)	0.31873 (10)	−0.21919 (14)	0.0398 (4)
N6	0.08080 (12)	0.61079 (11)	0.00524 (15)	0.0443 (4)
C1	0.37093 (12)	0.53225 (12)	0.14375 (15)	0.0328 (4)
C2	0.44253 (13)	0.47353 (12)	0.18471 (16)	0.0337 (4)
C3	0.46936 (14)	0.44942 (13)	0.29512 (17)	0.0408 (5)
C4	0.42342 (15)	0.47622 (14)	0.35629 (17)	0.0441 (5)
H4	0.4417	0.4577	0.4278	0.053*
C5	0.35069 (15)	0.53011 (15)	0.31371 (18)	0.0456 (5)
H5	0.3195	0.5473	0.3556	0.055*
C6	0.32498 (13)	0.55794 (13)	0.20875 (17)	0.0395 (5)
H6	0.2762	0.5946	0.1798	0.047*
C7	0.62574 (17)	0.4410 (2)	0.3822 (2)	0.0724 (8)
H7A	0.6307	0.4765	0.3264	0.109*
H7B	0.6744	0.4009	0.4067	0.109*
H7C	0.6279	0.4760	0.4421	0.109*
C8	0.34179 (13)	0.57118 (12)	0.03718 (16)	0.0357 (4)
H8	0.2863	0.5982	0.0119	0.043*
C9	0.34050 (14)	0.62316 (14)	−0.12656 (17)	0.0428 (5)
H9A	0.2767	0.6115	−0.1568	0.051*
H9B	0.3643	0.6052	−0.1793	0.051*
C10	0.35530 (15)	0.71901 (14)	−0.10719 (19)	0.0491 (6)
H10A	0.3274	0.7480	−0.1764	0.059*
H10B	0.3246	0.7375	−0.0617	0.059*
C11	0.45174 (15)	0.74753 (13)	−0.05485 (18)	0.0472 (5)
H11A	0.4529	0.8085	−0.0412	0.057*
H11B	0.4796	0.7192	0.0149	0.057*
C12	0.60227 (16)	0.75222 (18)	−0.0561 (2)	0.0653 (7)
H12A	0.6366	0.7408	−0.0990	0.098*
H12B	0.6250	0.7184	0.0089	0.098*
H12C	0.6069	0.8117	−0.0373	0.098*
C13	0.47408 (16)	0.77696 (15)	−0.22516 (18)	0.0542 (6)
H13A	0.4762	0.8374	−0.2117	0.081*
H13B	0.4135	0.7602	−0.2683	0.081*
H13C	0.5116	0.7635	−0.2634	0.081*
C14	0.14218 (13)	0.42832 (12)	0.24865 (16)	0.0359 (5)
C15	0.06605 (13)	0.47581 (12)	0.24231 (16)	0.0361 (5)
C16	0.04936 (15)	0.48005 (13)	0.33849 (17)	0.0424 (5)
C17	0.10847 (17)	0.44819 (14)	0.43617 (18)	0.0512 (6)
H17	0.0965	0.4543	0.4983	0.061*
C18	0.18630 (16)	0.40673 (14)	0.44204 (18)	0.0517 (6)
H18	0.2275	0.3867	0.5082	0.062*
C19	0.20132 (14)	0.39593 (13)	0.34964 (17)	0.0453 (5)
H19	0.2521	0.3663	0.3533	0.054*
C20	−0.10592 (18)	0.46990 (19)	0.2910 (2)	0.0693 (8)
H20A	−0.1103	0.4453	0.2234	0.104*
H20B	−0.1580	0.5042	0.2790	0.104*
H20C	−0.1022	0.4251	0.3416	0.104*
C21	0.16576 (13)	0.41259 (12)	0.15670 (17)	0.0376 (5)
H21	0.2213	0.3873	0.1723	0.045*
C22	0.16275 (13)	0.40526 (13)	−0.01820 (17)	0.0407 (5)
H22A	0.2264	0.4171	0.0166	0.049*
H22B	0.1383	0.4403	−0.0831	0.049*
C23	0.14924 (14)	0.31075 (14)	−0.05085 (18)	0.0461 (5)
H23A	0.1805	0.2991	−0.0980	0.055*
H23B	0.1772	0.2764	0.0141	0.055*
C24	0.05311 (14)	0.28187 (13)	−0.10793 (17)	0.0448 (5)
H24A	0.0520	0.2200	−0.1135	0.054*
H24B	0.0203	0.2977	−0.0639	0.054*
C25	0.04371 (16)	0.28787 (17)	−0.2978 (2)	0.0575 (6)
H25A	0.0398	0.2267	−0.3023	0.086*
H25B	0.1053	0.3049	−0.2736	0.086*
H25C	0.0102	0.3121	−0.3680	0.086*
C26	−0.09173 (14)	0.30137 (17)	−0.26210 (19)	0.0568 (6)
H26A	−0.1017	0.2408	−0.2647	0.085*
H26B	−0.1199	0.3248	−0.3339	0.085*
H26C	−0.1168	0.3274	−0.2154	0.085*
C27	0.36096 (14)	0.37389 (13)	−0.17575 (16)	0.0374 (5)
C28	0.12526 (14)	0.67114 (13)	0.02399 (16)	0.0378 (5)
H2	0.5041 (18)	0.6730 (7)	−0.132 (2)	0.080*
H5A	0.0166 (17)	0.3749 (7)	−0.207 (2)	0.080*

	U11	U22	U33	U12	U13	U23
Ni1	0.0356 (2)	0.02943 (18)	0.03020 (19)	−0.00061 (14)	0.01426 (15)	−0.00052 (14)
Ni2	0.03240 (19)	0.03016 (18)	0.02986 (19)	0.00455 (14)	0.00575 (15)	−0.00108 (14)
S1	0.0568 (4)	0.1032 (6)	0.0513 (4)	−0.0330 (4)	0.0194 (3)	−0.0272 (4)
S2	0.0585 (4)	0.0471 (3)	0.0575 (4)	−0.0116 (3)	0.0200 (3)	0.0014 (3)
O1	0.0518 (9)	0.0349 (7)	0.0406 (8)	0.0074 (6)	0.0264 (7)	0.0048 (6)
O2	0.0665 (11)	0.0570 (10)	0.0538 (10)	0.0182 (9)	0.0232 (9)	0.0186 (8)
O3	0.0434 (8)	0.0371 (7)	0.0321 (7)	0.0099 (6)	0.0084 (6)	−0.0007 (6)
O4	0.0635 (11)	0.0478 (9)	0.0506 (10)	0.0036 (8)	0.0261 (8)	−0.0062 (7)
N1	0.0351 (9)	0.0340 (8)	0.0331 (9)	−0.0007 (7)	0.0133 (7)	0.0008 (7)
N2	0.0445 (10)	0.0334 (9)	0.0467 (10)	0.0033 (8)	0.0204 (9)	0.0088 (8)
N3	0.0477 (11)	0.0399 (10)	0.0444 (10)	−0.0053 (8)	0.0141 (9)	−0.0058 (8)
N4	0.0327 (9)	0.0303 (8)	0.0365 (9)	0.0017 (7)	0.0087 (7)	−0.0034 (7)
N5	0.0380 (9)	0.0345 (9)	0.0427 (10)	0.0024 (8)	0.0113 (8)	−0.0082 (8)
N6	0.0416 (10)	0.0398 (10)	0.0475 (11)	0.0034 (8)	0.0133 (9)	−0.0019 (8)
C1	0.0340 (10)	0.0334 (9)	0.0331 (10)	−0.0070 (8)	0.0153 (9)	−0.0046 (8)
C2	0.0366 (11)	0.0312 (9)	0.0362 (11)	−0.0070 (8)	0.0174 (9)	−0.0030 (8)
C3	0.0460 (12)	0.0382 (11)	0.0384 (12)	−0.0023 (9)	0.0168 (10)	0.0028 (9)
C4	0.0545 (14)	0.0480 (12)	0.0317 (11)	−0.0076 (11)	0.0189 (10)	0.0008 (9)
C5	0.0523 (14)	0.0513 (12)	0.0427 (13)	−0.0087 (11)	0.0288 (11)	−0.0066 (11)
C6	0.0360 (11)	0.0429 (11)	0.0424 (12)	−0.0048 (9)	0.0184 (10)	−0.0035 (10)
C7	0.0526 (16)	0.108 (2)	0.0479 (15)	0.0185 (16)	0.0110 (13)	−0.0012 (15)
C8	0.0307 (10)	0.0389 (11)	0.0377 (11)	0.0003 (8)	0.0136 (9)	−0.0002 (9)
C9	0.0349 (11)	0.0547 (13)	0.0362 (11)	0.0008 (10)	0.0110 (9)	0.0086 (10)
C10	0.0525 (14)	0.0508 (13)	0.0524 (14)	0.0144 (11)	0.0296 (11)	0.0155 (11)
C11	0.0639 (15)	0.0369 (11)	0.0480 (13)	0.0042 (10)	0.0297 (12)	0.0034 (10)
C12	0.0496 (14)	0.0718 (17)	0.0665 (17)	−0.0102 (13)	0.0141 (13)	0.0197 (14)
C13	0.0613 (15)	0.0538 (14)	0.0496 (14)	0.0080 (12)	0.0240 (12)	0.0166 (11)
C14	0.0361 (11)	0.0297 (10)	0.0343 (11)	−0.0036 (8)	0.0056 (9)	0.0014 (8)
C15	0.0415 (11)	0.0263 (9)	0.0331 (11)	−0.0025 (8)	0.0068 (9)	−0.0021 (8)
C16	0.0512 (13)	0.0325 (10)	0.0416 (12)	−0.0030 (9)	0.0162 (11)	−0.0034 (9)
C17	0.0718 (16)	0.0454 (13)	0.0335 (12)	−0.0090 (12)	0.0176 (12)	−0.0002 (10)
C18	0.0560 (14)	0.0461 (13)	0.0386 (13)	−0.0057 (11)	0.0028 (11)	0.0095 (10)
C19	0.0406 (12)	0.0386 (11)	0.0443 (13)	−0.0019 (9)	0.0035 (10)	0.0066 (10)
C20	0.0624 (17)	0.0702 (17)	0.086 (2)	−0.0055 (14)	0.0402 (16)	−0.0064 (16)
C21	0.0303 (10)	0.0284 (9)	0.0460 (12)	0.0010 (8)	0.0064 (9)	0.0015 (9)
C22	0.0343 (11)	0.0443 (12)	0.0393 (11)	0.0029 (9)	0.0098 (9)	−0.0033 (9)
C23	0.0415 (12)	0.0449 (12)	0.0443 (12)	0.0087 (10)	0.0086 (10)	−0.0061 (10)
C24	0.0496 (13)	0.0352 (11)	0.0458 (12)	0.0050 (10)	0.0145 (10)	−0.0024 (9)
C25	0.0553 (15)	0.0642 (16)	0.0575 (15)	0.0057 (12)	0.0269 (12)	−0.0116 (13)
C26	0.0411 (12)	0.0712 (16)	0.0525 (14)	−0.0069 (12)	0.0123 (11)	−0.0120 (13)
C27	0.0397 (11)	0.0398 (11)	0.0367 (11)	0.0031 (9)	0.0194 (10)	0.0008 (9)
C28	0.0386 (11)	0.0380 (11)	0.0357 (11)	0.0089 (9)	0.0134 (9)	0.0035 (9)

Ni1—O1	2.0403 (13)	C7—H7B	0.9600
Ni1—O1i	2.0403 (13)	C7—H7C	0.9600
Ni1—N3i	2.0809 (18)	C8—H8	0.9300
Ni1—N3	2.0809 (18)	C9—C10	1.524 (3)
Ni1—N1	2.1102 (16)	C9—H9A	0.9700
Ni1—N1i	2.1102 (16)	C9—H9B	0.9700
Ni2—O3ii	2.0336 (14)	C10—C11	1.509 (3)
Ni2—O3	2.0336 (14)	C10—H10A	0.9700
Ni2—N4	2.0990 (15)	C10—H10B	0.9700
Ni2—N4ii	2.0990 (15)	C11—H11A	0.9700
Ni2—N6	2.1577 (19)	C11—H11B	0.9700
Ni2—N6ii	2.1577 (19)	C12—H12A	0.9600
S1—C27	1.630 (2)	C12—H12B	0.9600
S2—C28	1.643 (2)	C12—H12C	0.9600
O1—C2	1.316 (2)	C13—H13A	0.9600
O2—C3	1.386 (3)	C13—H13B	0.9600
O2—C7	1.428 (3)	C13—H13C	0.9600
O3—C15	1.306 (2)	C14—C19	1.410 (3)
O4—C16	1.394 (3)	C14—C15	1.415 (3)
O4—C20	1.422 (3)	C14—C21	1.447 (3)
N1—C8	1.277 (2)	C15—C16	1.418 (3)
N1—C9	1.481 (2)	C16—C17	1.376 (3)
N2—C12	1.489 (3)	C17—C18	1.394 (3)
N2—C13	1.490 (3)	C17—H17	0.9300
N2—C11	1.494 (3)	C18—C19	1.362 (3)
N2—H2	0.906 (10)	C18—H18	0.9300
N3—C27	1.150 (2)	C19—H19	0.9300
N4—C21	1.283 (2)	C20—H20A	0.9600
N4—C22	1.477 (3)	C20—H20B	0.9600
N5—C26	1.487 (3)	C20—H20C	0.9600
N5—C25	1.488 (3)	C21—H21	0.9300
N5—C24	1.497 (3)	C22—C23	1.533 (3)
N5—H5A	0.897 (10)	C22—H22A	0.9700
N6—C28	1.154 (3)	C22—H22B	0.9700
C1—C6	1.409 (3)	C23—C24	1.512 (3)
C1—C2	1.412 (3)	C23—H23A	0.9700
C1—C8	1.450 (3)	C23—H23B	0.9700
C2—C3	1.418 (3)	C24—H24A	0.9700
C3—C4	1.372 (3)	C24—H24B	0.9700
C4—C5	1.378 (3)	C25—H25A	0.9600
C4—H4	0.9300	C25—H25B	0.9600
C5—C6	1.371 (3)	C25—H25C	0.9600
C5—H5	0.9300	C26—H26A	0.9600
C6—H6	0.9300	C26—H26B	0.9600
C7—H7A	0.9600	C26—H26C	0.9600
O1—Ni1—O1i	180.00 (7)	C10—C9—H9B	109.1
O1—Ni1—N3i	87.54 (6)	H9A—C9—H9B	107.8
O1i—Ni1—N3i	92.46 (6)	C11—C10—C9	115.79 (18)
O1—Ni1—N3	92.46 (6)	C11—C10—H10A	108.3
O1i—Ni1—N3	87.54 (6)	C9—C10—H10A	108.3
N3i—Ni1—N3	180.00 (7)	C11—C10—H10B	108.3
O1—Ni1—N1	88.84 (6)	C9—C10—H10B	108.3
O1i—Ni1—N1	91.16 (6)	H10A—C10—H10B	107.4
N3i—Ni1—N1	92.66 (6)	N2—C11—C10	114.93 (18)
N3—Ni1—N1	87.34 (6)	N2—C11—H11A	108.5
O1—Ni1—N1i	91.16 (6)	C10—C11—H11A	108.5
O1i—Ni1—N1i	88.84 (6)	N2—C11—H11B	108.5
N3i—Ni1—N1i	87.34 (6)	C10—C11—H11B	108.5
N3—Ni1—N1i	92.66 (6)	H11A—C11—H11B	107.5
N1—Ni1—N1i	180.00 (7)	N2—C12—H12A	109.5
O3ii—Ni2—O3	180.000 (13)	N2—C12—H12B	109.5
O3ii—Ni2—N4	90.50 (6)	H12A—C12—H12B	109.5
O3—Ni2—N4	89.50 (6)	N2—C12—H12C	109.5
O3ii—Ni2—N4ii	89.50 (6)	H12A—C12—H12C	109.5
O3—Ni2—N4ii	90.50 (6)	H12B—C12—H12C	109.5
N4—Ni2—N4ii	180.0	N2—C13—H13A	109.5
O3ii—Ni2—N6	87.27 (6)	N2—C13—H13B	109.5
O3—Ni2—N6	92.73 (6)	H13A—C13—H13B	109.5
N4—Ni2—N6	87.02 (6)	N2—C13—H13C	109.5
N4ii—Ni2—N6	92.98 (6)	H13A—C13—H13C	109.5
O3ii—Ni2—N6ii	92.73 (6)	H13B—C13—H13C	109.5
O3—Ni2—N6ii	87.27 (6)	C19—C14—C15	119.7 (2)
N4—Ni2—N6ii	92.98 (6)	C19—C14—C21	116.57 (19)
N4ii—Ni2—N6ii	87.02 (6)	C15—C14—C21	123.70 (17)
N6—Ni2—N6ii	180.0	O3—C15—C14	124.64 (19)
C2—O1—Ni1	124.97 (12)	O3—C15—C16	118.99 (19)
C3—O2—C7	112.77 (19)	C14—C15—C16	116.35 (18)
C15—O3—Ni2	127.67 (13)	C17—C16—O4	119.5 (2)
C16—O4—C20	113.10 (18)	C17—C16—C15	122.4 (2)
C8—N1—C9	115.21 (16)	O4—C16—C15	118.04 (19)
C8—N1—Ni1	123.83 (13)	C16—C17—C18	120.0 (2)
C9—N1—Ni1	120.71 (13)	C16—C17—H17	120.0
C12—N2—C13	109.21 (17)	C18—C17—H17	120.0
C12—N2—C11	110.42 (18)	C19—C18—C17	119.2 (2)
C13—N2—C11	112.99 (17)	C19—C18—H18	120.4
C12—N2—H2	107.2 (17)	C17—C18—H18	120.4
C13—N2—H2	109.6 (18)	C18—C19—C14	122.0 (2)
C11—N2—H2	107.2 (17)	C18—C19—H19	119.0
C27—N3—Ni1	168.91 (17)	C14—C19—H19	119.0
C21—N4—C22	114.76 (16)	O4—C20—H20A	109.5
C21—N4—Ni2	124.16 (14)	O4—C20—H20B	109.5
C22—N4—Ni2	120.55 (12)	H20A—C20—H20B	109.5
C26—N5—C25	109.85 (17)	O4—C20—H20C	109.5
C26—N5—C24	111.28 (18)	H20A—C20—H20C	109.5
C25—N5—C24	112.90 (17)	H20B—C20—H20C	109.5
C26—N5—H5A	110.2 (17)	N4—C21—C14	127.99 (18)
C25—N5—H5A	110.1 (18)	N4—C21—H21	116.0
C24—N5—H5A	102.3 (18)	C14—C21—H21	116.0
C28—N6—Ni2	169.71 (18)	N4—C22—C23	112.64 (17)
C6—C1—C2	120.01 (18)	N4—C22—H22A	109.1
C6—C1—C8	116.18 (18)	C23—C22—H22A	109.1
C2—C1—C8	123.79 (18)	N4—C22—H22B	109.1
O1—C2—C1	123.56 (18)	C23—C22—H22B	109.1
O1—C2—C3	119.90 (18)	H22A—C22—H22B	107.8
C1—C2—C3	116.52 (18)	C24—C23—C22	115.85 (17)
C4—C3—O2	120.12 (19)	C24—C23—H23A	108.3
C4—C3—C2	121.65 (19)	C22—C23—H23A	108.3
O2—C3—C2	118.21 (19)	C24—C23—H23B	108.3
C3—C4—C5	121.2 (2)	C22—C23—H23B	108.3
C3—C4—H4	119.4	H23A—C23—H23B	107.4
C5—C4—H4	119.4	N5—C24—C23	114.12 (18)
C6—C5—C4	119.0 (2)	N5—C24—H24A	108.7
C6—C5—H5	120.5	C23—C24—H24A	108.7
C4—C5—H5	120.5	N5—C24—H24B	108.7
C5—C6—C1	121.4 (2)	C23—C24—H24B	108.7
C5—C6—H6	119.3	H24A—C24—H24B	107.6
C1—C6—H6	119.3	N5—C25—H25A	109.5
O2—C7—H7A	109.5	N5—C25—H25B	109.5
O2—C7—H7B	109.5	H25A—C25—H25B	109.5
H7A—C7—H7B	109.5	N5—C25—H25C	109.5
O2—C7—H7C	109.5	H25A—C25—H25C	109.5
H7A—C7—H7C	109.5	H25B—C25—H25C	109.5
H7B—C7—H7C	109.5	N5—C26—H26A	109.5
N1—C8—C1	127.30 (18)	N5—C26—H26B	109.5
N1—C8—H8	116.3	H26A—C26—H26B	109.5
C1—C8—H8	116.3	N5—C26—H26C	109.5
N1—C9—C10	112.56 (17)	H26A—C26—H26C	109.5
N1—C9—H9A	109.1	H26B—C26—H26C	109.5
C10—C9—H9A	109.1	N3—C27—S1	178.0 (2)
N1—C9—H9B	109.1	N6—C28—S2	177.5 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O1i	0.91 (1)	1.78 (1)	2.668 (2)	167 (3)
N5—H5A···O3ii	0.90 (1)	1.96 (2)	2.764 (2)	149 (2)

Table 1

Selected bond lengths (Å)

Ni1—O1	2.0403 (13)
Ni1—N3	2.0809 (18)
Ni1—N1	2.1102 (16)
Ni2—O3	2.0336 (14)
Ni2—N4	2.0990 (15)
Ni2—N6	2.1577 (19)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O1i	0.91 (1)	1.78 (1)	2.668 (2)	167 (3)
N5—H5A⋯O3ii	0.90 (1)	1.96 (2)	2.764 (2)	149 (2)

Symmetry codes: (i) ; (ii) .