Bis{2-[(2-hy-droxy-2-methyl-prop-yl)imino-meth-yl]-4-nitro-phenolato}nickel(II) dimethyl-formamide monosolvate.

In the title compound, [Ni(C(11)H(13)N(2)O(4))(2)]·C(3)H(7)NO, the Ni(II) ion is octa-hedrally coordinated in an N(2)O(4) environment by two identical Schiff base ligands. The Ni-O bond lengths range from 2.004 (2) to 2.106 (2) Å, while the Ni-N bond lengths are 2.038 (2) and 2.0465 (19) Å. The cis bond angles range from 78.64 (8) to 97.30 (8)°, with the former being due to the small bite of the amino-alcohol ligand, while the trans bond angles range from 167.86 (8) to 171.23 (8)°. One of the alcohol H atoms forms a hydrogen bond with the dimethyl-formamide (DMF) solvent mol-ecule, while the other links mol-ecules into chains along the b axis through inter-molecular O-H⋯O hydrogen bonds. There are bifurcated C-H⋯O inter-actions involving one of the nitro groups between parallel stacks of mol-ecules in the b-axis direction.

Related literature

For similar nickel Schiff base complexes, see: Ali et al. (2006 ▶); Butcher et al. (1981 ▶, 2009 ▶); Gultneh et al. (1998 ▶); Mustafaa et al. (2009 ▶); Zhang et al. (2010 ▶).

Experimental

Crystal data

[Ni(C11H13N2O4)2]·C3H7NO

M = 606.27

Monoclinic,

a = 11.42279 (16) Å

b = 11.42936 (18) Å

c = 21.4903 (3) Å

β = 99.1120 (14)°

V = 2770.26 (7) Å3

Z = 4

Cu Kα radiation

μ = 1.54 mm−1

T = 295 K

0.44 × 0.21 × 0.18 mm

Data collection

Oxford Diffraction Xcalibur Ruby Gemini diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009 ▶) T min = 0.650, T max = 1.000

13929 measured reflections

5826 independent reflections

4514 reflections with I > 2σ(I)

R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.055

wR(F 2) = 0.174

S = 1.05

5826 reflections

367 parameters

H-atom parameters constrained

Δρmax = 0.56 e Å−3

Δρmin = −0.53 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; 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 datablock(s) I, global. DOI: 10.1107/S1600536811031229/jj2096sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811031229/jj2096Isup2.hkl

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

[Ni(C11H13N2O4)2]·C3H7NO	F(000) = 1272
Mr = 606.27	Dx = 1.454 Mg m−3
Monoclinic, P21/n	Cu Kα radiation, λ = 1.54184 Å
Hall symbol: -P 2yn	Cell parameters from 6836 reflections
a = 11.42279 (16) Å	θ = 4.4–77.3°
b = 11.42936 (18) Å	µ = 1.54 mm−1
c = 21.4903 (3) Å	T = 295 K
β = 99.1120 (14)°	Needle, pale-green
V = 2770.26 (7) Å3	0.44 × 0.21 × 0.18 mm
Z = 4

Oxford Diffraction Xcalibur Ruby Gemini diffractometer	5826 independent reflections
Radiation source: Enhance (Cu) X-ray Source	4514 reflections with I > 2σ(I)
graphite	Rint = 0.026
Detector resolution: 10.5081 pixels mm-1	θmax = 77.5°, θmin = 4.4°
ω scans	h = −13→14
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)	k = −14→13
Tmin = 0.650, Tmax = 1.000	l = −26→17
13929 measured reflections

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)] = 0.055	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.174	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.116P)2 + 0.4736P] where P = (Fo2 + 2Fc2)/3
5826 reflections	(Δ/σ)max = 0.001
367 parameters	Δρmax = 0.56 e Å−3
0 restraints	Δρmin = −0.53 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
Ni	0.28214 (3)	0.69956 (4)	0.739938 (17)	0.04163 (16)
O1A	0.13279 (18)	0.7923 (2)	0.73843 (9)	0.0627 (6)
O2A	0.43631 (19)	0.5964 (2)	0.75995 (9)	0.0672 (6)
H2A	0.4851	0.5947	0.7358	0.081*
O3A	−0.2832 (2)	0.8371 (3)	0.88948 (13)	0.0905 (8)
O4A	−0.1546 (3)	0.7581 (5)	0.95965 (12)	0.1320 (15)
O1B	0.38319 (17)	0.84650 (17)	0.74068 (8)	0.0505 (4)
O2B	0.1755 (2)	0.5507 (2)	0.71838 (10)	0.0850 (8)
H2B	0.1676	0.4831	0.7297	0.102*
O3B	0.7678 (3)	1.0122 (4)	0.58611 (14)	0.1350 (16)
O4B	0.6486 (2)	0.9308 (3)	0.51235 (11)	0.0932 (9)
O1S	0.6253 (5)	0.6221 (4)	0.6974 (3)	0.190 (3)
N1A	0.29366 (18)	0.67706 (18)	0.83479 (9)	0.0418 (4)
N2A	−0.1859 (2)	0.7931 (3)	0.90622 (13)	0.0739 (8)
N1B	0.26685 (17)	0.69504 (17)	0.64379 (9)	0.0395 (4)
N2B	0.6746 (2)	0.9632 (3)	0.56688 (13)	0.0737 (8)
N1S	0.6828 (3)	0.6268 (4)	0.60657 (18)	0.0901 (10)
C1A	0.0612 (2)	0.7858 (2)	0.77807 (11)	0.0433 (5)
C2A	−0.0573 (2)	0.8288 (3)	0.76076 (13)	0.0530 (6)
H2AA	−0.0803	0.8582	0.7203	0.064*
C3A	−0.1370 (2)	0.8284 (3)	0.80106 (13)	0.0536 (6)
H3AA	−0.2134	0.8566	0.7883	0.064*
C4A	−0.1031 (2)	0.7851 (3)	0.86214 (13)	0.0524 (6)
C5A	0.0081 (2)	0.7403 (3)	0.88111 (11)	0.0485 (6)
H5AA	0.0282	0.7108	0.9217	0.058*
C6A	0.0916 (2)	0.7383 (2)	0.84022 (11)	0.0421 (5)
C7A	0.2064 (2)	0.6891 (2)	0.86487 (11)	0.0444 (5)
H7AA	0.2177	0.6638	0.9065	0.053*
C8A	0.4050 (2)	0.6210 (2)	0.86711 (11)	0.0473 (5)
C9A	0.3801 (3)	0.4930 (3)	0.88058 (18)	0.0779 (9)
H9AA	0.3447	0.4553	0.8423	0.117*
H9AB	0.3268	0.4889	0.9109	0.117*
H9AC	0.4530	0.4544	0.8971	0.117*
C10A	0.4563 (3)	0.6847 (3)	0.92732 (16)	0.0710 (9)
H10A	0.4733	0.7643	0.9176	0.107*
H10B	0.5280	0.6467	0.9464	0.107*
H10C	0.3999	0.6835	0.9560	0.107*
C11A	0.4935 (3)	0.6308 (4)	0.82125 (15)	0.0748 (10)
H11A	0.5215	0.7107	0.8201	0.090*
H11B	0.5612	0.5806	0.8348	0.090*
C1B	0.4490 (2)	0.8726 (2)	0.69862 (10)	0.0405 (5)
C2B	0.5510 (2)	0.9442 (2)	0.71580 (12)	0.0494 (6)
H2BA	0.5686	0.9712	0.7570	0.059*
C3B	0.6240 (2)	0.9745 (3)	0.67371 (13)	0.0532 (6)
H3BA	0.6914	1.0196	0.6865	0.064*
C4B	0.5961 (2)	0.9370 (3)	0.61158 (12)	0.0512 (6)
C5B	0.4966 (2)	0.8706 (2)	0.59204 (11)	0.0466 (5)
H5BA	0.4778	0.8493	0.5499	0.056*
C6B	0.4235 (2)	0.8348 (2)	0.63480 (11)	0.0410 (5)
C7B	0.3283 (2)	0.7547 (2)	0.61084 (10)	0.0418 (5)
H7BA	0.3106	0.7463	0.5673	0.050*
C8B	0.1836 (2)	0.6052 (2)	0.61156 (11)	0.0485 (6)
C9B	0.2573 (4)	0.5016 (3)	0.5970 (2)	0.0877 (12)
H9BA	0.3069	0.5244	0.5670	0.132*
H9BB	0.2058	0.4392	0.5798	0.132*
H9BC	0.3059	0.4754	0.6350	0.132*
C10B	0.1066 (3)	0.6519 (3)	0.55286 (14)	0.0693 (9)
H10D	0.0621	0.7179	0.5638	0.104*
H10E	0.0531	0.5918	0.5348	0.104*
H10F	0.1560	0.6755	0.5228	0.104*
C11B	0.1044 (3)	0.5691 (3)	0.65874 (14)	0.0709 (9)
H11C	0.0464	0.6298	0.6620	0.085*
H11D	0.0624	0.4977	0.6448	0.085*
C1S	0.6898 (11)	0.6407 (7)	0.6647 (5)	0.207 (5)
H1SA	0.7614	0.6721	0.6842	0.248*
C2S	0.7801 (10)	0.6597 (10)	0.5804 (6)	0.282 (7)
H2SA	0.8299	0.7096	0.6093	0.423*
H2SB	0.7546	0.7011	0.5418	0.423*
H2SC	0.8238	0.5913	0.5720	0.423*
C3S	0.5866 (8)	0.5788 (7)	0.5676 (5)	0.245 (6)
H3SA	0.5195	0.5767	0.5895	0.368*
H3SB	0.6056	0.5008	0.5561	0.368*
H3SC	0.5679	0.6258	0.5303	0.368*

	U11	U22	U33	U12	U13	U23
Ni	0.0460 (2)	0.0483 (3)	0.0325 (2)	−0.00103 (17)	0.01224 (16)	0.00310 (16)
O1A	0.0568 (11)	0.0894 (15)	0.0464 (10)	0.0168 (10)	0.0217 (8)	0.0294 (10)
O2A	0.0693 (12)	0.0940 (15)	0.0410 (9)	0.0308 (11)	0.0169 (9)	0.0006 (10)
O3A	0.0570 (13)	0.139 (2)	0.0816 (17)	0.0211 (14)	0.0310 (12)	0.0058 (16)
O4A	0.095 (2)	0.260 (4)	0.0514 (15)	0.061 (3)	0.0409 (13)	0.037 (2)
O1B	0.0590 (10)	0.0576 (10)	0.0398 (8)	−0.0098 (8)	0.0226 (8)	−0.0105 (8)
O2B	0.1166 (19)	0.0817 (16)	0.0496 (11)	−0.0528 (15)	−0.0091 (12)	0.0236 (11)
O3B	0.0959 (19)	0.233 (4)	0.0830 (18)	−0.101 (3)	0.0347 (15)	−0.025 (2)
O4B	0.0895 (17)	0.144 (3)	0.0539 (13)	−0.0486 (17)	0.0356 (12)	−0.0146 (14)
O1S	0.217 (5)	0.130 (4)	0.268 (7)	0.044 (4)	0.176 (5)	0.052 (4)
N1A	0.0447 (10)	0.0480 (10)	0.0334 (9)	0.0018 (8)	0.0082 (8)	−0.0002 (8)
N2A	0.0567 (14)	0.114 (2)	0.0565 (15)	0.0125 (14)	0.0244 (12)	0.0019 (15)
N1B	0.0418 (9)	0.0437 (10)	0.0341 (9)	−0.0043 (8)	0.0095 (7)	0.0010 (7)
N2B	0.0626 (14)	0.105 (2)	0.0576 (15)	−0.0316 (15)	0.0224 (12)	0.0003 (15)
N1S	0.0749 (19)	0.105 (3)	0.089 (2)	0.0207 (18)	0.0082 (17)	−0.022 (2)
C1A	0.0443 (12)	0.0489 (12)	0.0383 (11)	−0.0007 (10)	0.0118 (9)	0.0044 (10)
C2A	0.0508 (14)	0.0653 (16)	0.0437 (13)	0.0049 (12)	0.0097 (11)	0.0116 (12)
C3A	0.0461 (13)	0.0664 (16)	0.0489 (14)	0.0071 (12)	0.0095 (11)	0.0011 (12)
C4A	0.0492 (13)	0.0673 (16)	0.0432 (13)	0.0007 (12)	0.0153 (11)	−0.0008 (12)
C5A	0.0517 (13)	0.0632 (15)	0.0327 (11)	−0.0004 (12)	0.0128 (10)	0.0020 (11)
C6A	0.0447 (11)	0.0484 (12)	0.0343 (11)	−0.0022 (10)	0.0100 (9)	0.0007 (9)
C7A	0.0499 (12)	0.0564 (14)	0.0275 (10)	−0.0011 (10)	0.0081 (9)	0.0035 (9)
C8A	0.0473 (12)	0.0552 (14)	0.0381 (11)	0.0074 (11)	0.0030 (9)	−0.0033 (10)
C9A	0.087 (2)	0.0625 (19)	0.081 (2)	0.0095 (17)	0.0050 (18)	0.0098 (17)
C10A	0.0604 (17)	0.091 (2)	0.0569 (17)	0.0084 (16)	−0.0045 (14)	−0.0163 (16)
C11A	0.0565 (16)	0.113 (3)	0.0553 (16)	0.0244 (18)	0.0109 (13)	0.0081 (18)
C1B	0.0423 (11)	0.0430 (11)	0.0384 (11)	0.0006 (9)	0.0129 (9)	−0.0035 (9)
C2B	0.0524 (13)	0.0549 (14)	0.0418 (12)	−0.0059 (11)	0.0106 (10)	−0.0100 (11)
C3B	0.0491 (13)	0.0584 (15)	0.0534 (14)	−0.0153 (11)	0.0116 (11)	−0.0055 (12)
C4B	0.0480 (13)	0.0610 (15)	0.0473 (13)	−0.0086 (11)	0.0159 (11)	0.0004 (11)
C5B	0.0475 (12)	0.0569 (14)	0.0371 (11)	−0.0038 (11)	0.0123 (9)	0.0009 (10)
C6B	0.0412 (11)	0.0451 (11)	0.0386 (11)	−0.0018 (9)	0.0116 (9)	0.0001 (9)
C7B	0.0450 (11)	0.0512 (13)	0.0307 (10)	−0.0042 (10)	0.0107 (8)	−0.0003 (9)
C8B	0.0529 (13)	0.0521 (13)	0.0403 (12)	−0.0125 (11)	0.0068 (10)	0.0004 (10)
C9B	0.092 (3)	0.0579 (19)	0.112 (3)	−0.0058 (18)	0.014 (2)	−0.024 (2)
C10B	0.0609 (17)	0.095 (2)	0.0488 (15)	−0.0250 (16)	−0.0020 (13)	0.0124 (16)
C11B	0.0742 (19)	0.089 (2)	0.0488 (15)	−0.0383 (17)	0.0064 (14)	0.0091 (15)
C1S	0.334 (13)	0.135 (6)	0.194 (8)	0.114 (8)	0.173 (9)	0.055 (6)
C2S	0.200 (10)	0.238 (12)	0.45 (2)	0.030 (9)	0.191 (12)	0.004 (12)
C3S	0.198 (8)	0.150 (7)	0.334 (13)	0.077 (6)	−0.126 (9)	−0.084 (8)

Ni—O1A	2.004 (2)	C8A—C9A	1.526 (4)
Ni—O1B	2.0365 (19)	C9A—H9AA	0.9600
Ni—N1A	2.038 (2)	C9A—H9AB	0.9600
Ni—N1B	2.0465 (19)	C9A—H9AC	0.9600
Ni—O2B	2.101 (2)	C10A—H10A	0.9600
Ni—O2A	2.106 (2)	C10A—H10B	0.9600
O1A—C1A	1.273 (3)	C10A—H10C	0.9600
O2A—C11A	1.429 (4)	C11A—H11A	0.9700
O2A—H2A	0.8200	C11A—H11B	0.9700
O3A—N2A	1.222 (4)	C1B—C6B	1.423 (3)
O4A—N2A	1.215 (4)	C1B—C2B	1.423 (3)
O1B—C1B	1.298 (3)	C2B—C3B	1.369 (4)
O2B—C11B	1.420 (4)	C2B—H2BA	0.9300
O2B—H2B	0.8200	C3B—C4B	1.391 (4)
O3B—N2B	1.216 (3)	C3B—H3BA	0.9300
O4B—N2B	1.220 (3)	C4B—C5B	1.375 (4)
O1S—C1S	1.115 (8)	C5B—C6B	1.397 (3)
N1A—C7A	1.278 (3)	C5B—H5BA	0.9300
N1A—C8A	1.494 (3)	C6B—C7B	1.452 (3)
N2A—C4A	1.443 (4)	C7B—H7BA	0.9300
N1B—C7B	1.272 (3)	C8B—C9B	1.514 (5)
N1B—C8B	1.493 (3)	C8B—C10B	1.516 (4)
N2B—C4B	1.446 (3)	C8B—C11B	1.519 (4)
N1S—C1S	1.250 (9)	C9B—H9BA	0.9600
N1S—C2S	1.375 (10)	C9B—H9BB	0.9600
N1S—C3S	1.385 (8)	C9B—H9BC	0.9600
C1A—C6A	1.433 (3)	C10B—H10D	0.9600
C1A—C2A	1.433 (4)	C10B—H10E	0.9600
C2A—C3A	1.352 (4)	C10B—H10F	0.9600
C2A—H2AA	0.9300	C11B—H11C	0.9700
C3A—C4A	1.399 (4)	C11B—H11D	0.9700
C3A—H3AA	0.9300	C1S—H1SA	0.9300
C4A—C5A	1.371 (4)	C2S—H2SA	0.9600
C5A—C6A	1.396 (3)	C2S—H2SB	0.9600
C5A—H5AA	0.9300	C2S—H2SC	0.9600
C6A—C7A	1.448 (3)	C3S—H3SA	0.9600
C7A—H7AA	0.9300	C3S—H3SB	0.9600
C8A—C10A	1.519 (4)	C3S—H3SC	0.9600
C8A—C11A	1.523 (4)
O1A—Ni—O1B	92.52 (9)	C8A—C10A—H10B	109.5
O1A—Ni—N1A	90.16 (8)	H10A—C10A—H10B	109.5
O1B—Ni—N1A	98.60 (8)	C8A—C10A—H10C	109.5
O1A—Ni—N1B	93.48 (8)	H10A—C10A—H10C	109.5
O1B—Ni—N1B	89.22 (7)	H10B—C10A—H10C	109.5
N1A—Ni—N1B	171.23 (8)	O2A—C11A—C8A	108.8 (3)
O1A—Ni—O2B	87.84 (11)	O2A—C11A—H11A	109.9
O1B—Ni—O2B	167.86 (8)	C8A—C11A—H11A	109.9
N1A—Ni—O2B	93.54 (8)	O2A—C11A—H11B	109.9
N1B—Ni—O2B	78.64 (8)	C8A—C11A—H11B	109.9
O1A—Ni—O2A	168.90 (8)	H11A—C11A—H11B	108.3
O1B—Ni—O2A	90.31 (9)	O1B—C1B—C6B	123.3 (2)
N1A—Ni—O2A	78.79 (8)	O1B—C1B—C2B	119.5 (2)
N1B—Ni—O2A	97.30 (8)	C6B—C1B—C2B	117.3 (2)
O2B—Ni—O2A	91.64 (11)	C3B—C2B—C1B	122.3 (2)
C1A—O1A—Ni	126.42 (16)	C3B—C2B—H2BA	118.9
C11A—O2A—Ni	106.24 (17)	C1B—C2B—H2BA	118.9
C11A—O2A—H2A	109.5	C2B—C3B—C4B	119.0 (2)
Ni—O2A—H2A	120.9	C2B—C3B—H3BA	120.5
C1B—O1B—Ni	125.03 (15)	C4B—C3B—H3BA	120.5
C11B—O2B—Ni	107.94 (18)	C5B—C4B—C3B	121.1 (2)
C11B—O2B—H2B	109.5	C5B—C4B—N2B	118.7 (2)
Ni—O2B—H2B	141.8	C3B—C4B—N2B	120.1 (2)
C7A—N1A—C8A	119.1 (2)	C4B—C5B—C6B	120.8 (2)
C7A—N1A—Ni	124.07 (17)	C4B—C5B—H5BA	119.6
C8A—N1A—Ni	115.76 (15)	C6B—C5B—H5BA	119.6
O4A—N2A—O3A	122.1 (3)	C5B—C6B—C1B	119.5 (2)
O4A—N2A—C4A	118.3 (3)	C5B—C6B—C7B	116.3 (2)
O3A—N2A—C4A	119.5 (3)	C1B—C6B—C7B	124.1 (2)
C7B—N1B—C8B	118.5 (2)	N1B—C7B—C6B	126.1 (2)
C7B—N1B—Ni	125.61 (17)	N1B—C7B—H7BA	116.9
C8B—N1B—Ni	115.59 (14)	C6B—C7B—H7BA	116.9
O3B—N2B—O4B	122.2 (3)	N1B—C8B—C9B	107.4 (2)
O3B—N2B—C4B	118.1 (3)	N1B—C8B—C10B	112.8 (2)
O4B—N2B—C4B	119.6 (2)	C9B—C8B—C10B	111.8 (3)
C1S—N1S—C2S	116.5 (9)	N1B—C8B—C11B	106.3 (2)
C1S—N1S—C3S	125.0 (9)	C9B—C8B—C11B	109.5 (3)
C2S—N1S—C3S	118.5 (8)	C10B—C8B—C11B	108.9 (2)
O1A—C1A—C6A	124.0 (2)	C8B—C9B—H9BA	109.5
O1A—C1A—C2A	119.1 (2)	C8B—C9B—H9BB	109.5
C6A—C1A—C2A	116.8 (2)	H9BA—C9B—H9BB	109.5
C3A—C2A—C1A	122.4 (2)	C8B—C9B—H9BC	109.5
C3A—C2A—H2AA	118.8	H9BA—C9B—H9BC	109.5
C1A—C2A—H2AA	118.8	H9BB—C9B—H9BC	109.5
C2A—C3A—C4A	119.2 (2)	C8B—C10B—H10D	109.5
C2A—C3A—H3AA	120.4	C8B—C10B—H10E	109.5
C4A—C3A—H3AA	120.4	H10D—C10B—H10E	109.5
C5A—C4A—C3A	121.1 (2)	C8B—C10B—H10F	109.5
C5A—C4A—N2A	120.1 (2)	H10D—C10B—H10F	109.5
C3A—C4A—N2A	118.8 (3)	H10E—C10B—H10F	109.5
C4A—C5A—C6A	120.8 (2)	O2B—C11B—C8B	109.1 (2)
C4A—C5A—H5AA	119.6	O2B—C11B—H11C	109.9
C6A—C5A—H5AA	119.6	C8B—C11B—H11C	109.9
C5A—C6A—C1A	119.5 (2)	O2B—C11B—H11D	109.9
C5A—C6A—C7A	116.5 (2)	C8B—C11B—H11D	109.9
C1A—C6A—C7A	124.1 (2)	H11C—C11B—H11D	108.3
N1A—C7A—C6A	126.2 (2)	O1S—C1S—N1S	131.3 (14)
N1A—C7A—H7AA	116.9	O1S—C1S—H1SA	114.3
C6A—C7A—H7AA	116.9	N1S—C1S—H1SA	114.3
N1A—C8A—C10A	112.0 (2)	N1S—C2S—H2SA	109.5
N1A—C8A—C11A	105.7 (2)	N1S—C2S—H2SB	109.5
C10A—C8A—C11A	108.1 (3)	H2SA—C2S—H2SB	109.5
N1A—C8A—C9A	109.2 (2)	N1S—C2S—H2SC	109.5
C10A—C8A—C9A	110.9 (3)	H2SA—C2S—H2SC	109.5
C11A—C8A—C9A	110.9 (3)	H2SB—C2S—H2SC	109.5
C8A—C9A—H9AA	109.5	N1S—C3S—H3SA	109.5
C8A—C9A—H9AB	109.5	N1S—C3S—H3SB	109.5
H9AA—C9A—H9AB	109.5	H3SA—C3S—H3SB	109.5
C8A—C9A—H9AC	109.5	N1S—C3S—H3SC	109.5
H9AA—C9A—H9AC	109.5	H3SA—C3S—H3SC	109.5
H9AB—C9A—H9AC	109.5	H3SB—C3S—H3SC	109.5
C8A—C10A—H10A	109.5
O1B—Ni—O1A—C1A	−123.2 (2)	C2A—C1A—C6A—C5A	−2.6 (4)
N1A—Ni—O1A—C1A	−24.5 (2)	O1A—C1A—C6A—C7A	−1.7 (4)
N1B—Ni—O1A—C1A	147.5 (2)	C2A—C1A—C6A—C7A	178.7 (2)
O2B—Ni—O1A—C1A	69.0 (2)	C8A—N1A—C7A—C6A	−178.2 (2)
O2A—Ni—O1A—C1A	−18.5 (7)	Ni—N1A—C7A—C6A	−10.8 (4)
O1A—Ni—O2A—C11A	−40.2 (6)	C5A—C6A—C7A—N1A	178.5 (3)
O1B—Ni—O2A—C11A	64.6 (2)	C1A—C6A—C7A—N1A	−2.8 (4)
N1A—Ni—O2A—C11A	−34.1 (2)	C7A—N1A—C8A—C10A	−57.3 (3)
N1B—Ni—O2A—C11A	153.9 (2)	Ni—N1A—C8A—C10A	134.3 (2)
O2B—Ni—O2A—C11A	−127.3 (2)	C7A—N1A—C8A—C11A	−174.7 (3)
O1A—Ni—O1B—C1B	−121.5 (2)	Ni—N1A—C8A—C11A	16.9 (3)
N1A—Ni—O1B—C1B	148.0 (2)	C7A—N1A—C8A—C9A	66.0 (3)
N1B—Ni—O1B—C1B	−28.0 (2)	Ni—N1A—C8A—C9A	−102.5 (2)
O2B—Ni—O1B—C1B	−30.0 (6)	Ni—O2A—C11A—C8A	53.9 (3)
O2A—Ni—O1B—C1B	69.3 (2)	N1A—C8A—C11A—O2A	−46.3 (3)
O1A—Ni—O2B—C11B	62.1 (2)	C10A—C8A—C11A—O2A	−166.4 (3)
O1B—Ni—O2B—C11B	−29.9 (6)	C9A—C8A—C11A—O2A	71.9 (3)
N1A—Ni—O2B—C11B	152.1 (2)	Ni—O1B—C1B—C6B	28.5 (3)
N1B—Ni—O2B—C11B	−31.9 (2)	Ni—O1B—C1B—C2B	−152.63 (19)
O2A—Ni—O2B—C11B	−129.0 (2)	O1B—C1B—C2B—C3B	179.8 (3)
O1A—Ni—N1A—C7A	19.7 (2)	C6B—C1B—C2B—C3B	−1.3 (4)
O1B—Ni—N1A—C7A	112.2 (2)	C1B—C2B—C3B—C4B	1.8 (4)
O2B—Ni—N1A—C7A	−68.2 (2)	C2B—C3B—C4B—C5B	0.2 (4)
O2A—Ni—N1A—C7A	−159.2 (2)	C2B—C3B—C4B—N2B	−177.1 (3)
O1A—Ni—N1A—C8A	−172.58 (18)	O3B—N2B—C4B—C5B	−173.0 (4)
O1B—Ni—N1A—C8A	−80.00 (18)	O4B—N2B—C4B—C5B	3.4 (5)
O2B—Ni—N1A—C8A	99.57 (18)	O3B—N2B—C4B—C3B	4.3 (5)
O2A—Ni—N1A—C8A	8.60 (17)	O4B—N2B—C4B—C3B	−179.3 (3)
O1A—Ni—N1B—C7B	105.4 (2)	C3B—C4B—C5B—C6B	−2.7 (4)
O1B—Ni—N1B—C7B	12.9 (2)	N2B—C4B—C5B—C6B	174.6 (3)
O2B—Ni—N1B—C7B	−167.5 (2)	C4B—C5B—C6B—C1B	3.2 (4)
O2A—Ni—N1B—C7B	−77.3 (2)	C4B—C5B—C6B—C7B	−173.6 (2)
O1A—Ni—N1B—C8B	−80.53 (18)	O1B—C1B—C6B—C5B	177.6 (2)
O1B—Ni—N1B—C8B	−173.01 (17)	C2B—C1B—C6B—C5B	−1.3 (3)
O2B—Ni—N1B—C8B	6.57 (18)	O1B—C1B—C6B—C7B	−5.9 (4)
O2A—Ni—N1B—C8B	96.78 (18)	C2B—C1B—C6B—C7B	175.3 (2)
Ni—O1A—C1A—C6A	19.7 (4)	C8B—N1B—C7B—C6B	−171.9 (2)
Ni—O1A—C1A—C2A	−160.7 (2)	Ni—N1B—C7B—C6B	2.0 (4)
O1A—C1A—C2A—C3A	−177.8 (3)	C5B—C6B—C7B—N1B	165.8 (2)
C6A—C1A—C2A—C3A	1.8 (4)	C1B—C6B—C7B—N1B	−10.8 (4)
C1A—C2A—C3A—C4A	0.4 (5)	C7B—N1B—C8B—C9B	75.3 (3)
C2A—C3A—C4A—C5A	−1.9 (5)	Ni—N1B—C8B—C9B	−99.2 (3)
C2A—C3A—C4A—N2A	175.4 (3)	C7B—N1B—C8B—C10B	−48.3 (3)
O4A—N2A—C4A—C5A	−0.8 (5)	Ni—N1B—C8B—C10B	137.2 (2)
O3A—N2A—C4A—C5A	177.3 (3)	C7B—N1B—C8B—C11B	−167.5 (2)
O4A—N2A—C4A—C3A	−178.1 (4)	Ni—N1B—C8B—C11B	18.0 (3)
O3A—N2A—C4A—C3A	0.1 (5)	Ni—O2B—C11B—C8B	51.5 (3)
C3A—C4A—C5A—C6A	1.0 (4)	N1B—C8B—C11B—O2B	−45.2 (4)
N2A—C4A—C5A—C6A	−176.2 (3)	C9B—C8B—C11B—O2B	70.6 (3)
C4A—C5A—C6A—C1A	1.2 (4)	C10B—C8B—C11B—O2B	−166.9 (3)
C4A—C5A—C6A—C7A	180.0 (3)	C2S—N1S—C1S—O1S	179.8 (8)
O1A—C1A—C6A—C5A	177.0 (3)	C3S—N1S—C1S—O1S	−1.7 (12)

D—H···A	D—H	H···A	D···A	D—H···A
O2A—H2A···O1S	0.82	1.94	2.734 (5)	163.
O2B—H2B···O1Bi	0.82	1.81	2.619 (3)	166.
C9A—H9AA···O1Ai	0.96	2.59	3.422 (4)	146.
C11A—H11B···O3Bii	0.97	2.50	3.394 (4)	153.
C5B—H5BA···O4Aiii	0.93	2.57	3.418 (4)	151.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2A—H2A⋯O1S	0.82	1.94	2.734 (5)	163
O2B—H2B⋯O1Bi	0.82	1.81	2.619 (3)	166
C9A—H9AA⋯O1Ai	0.96	2.59	3.422 (4)	146
C11A—H11B⋯O3Bii	0.97	2.50	3.394 (4)	153
C5B—H5BA⋯O4Aiii	0.93	2.57	3.418 (4)	151

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