Bis{μ-N-[(E)-4-benz-yloxy-2-oxidobenzyl-idene]-4-nitro-benzene-carbo-hydrazidato}bis-[di-aqua-nickel(II)] di-methyl-formamide tetra-solvate.

The molecule of the title complex, [Ni2(C21H15N3O5)2(H2O)4]·4C3H7NO, is located on an inversion centre. This results in a dimeric Ni(II) complex, with the two Ni(II) atoms bridged by phenolate O atoms. The tridentate ligand is chelated to each Ni(II) atom via one N and two O atoms of the imino-late form of the hydrazide moiety, which has the same conformation as the free ligand. The coordination geometry around each Ni(II) ion is slightly distorted octa-hedral. A supra-molecular three-dimensional architecture is created by dominant inter-molecular O-H⋯N, O-H⋯O and C-H⋯O hydrogen-bonding inter-actions. These are augmented by two C-H⋯π inter-actions and a π-π inter-action with a centroid-centroid distance of 3.681 (2) Å.

Related literature

For biological applications of hydrazinecarboxamide and its derivatives, see: Lakshmi et al. (2011 ▶); Prasanna & Kumar (2013 ▶); Singh et al. (2007 ▶); Naseema et al. (2010 ▶). For the synthesis of related compounds, see: Joseph et al. (2013 ▶). For related structures, see: Joseph et al. (2012 ▶); Raj & Kurup (2007 ▶). For standard bond lengths, see: Allen et al. (1987 ▶).

Experimental

Crystal data

[Ni2(C21H15N3O5)2(H2O)4]·4C3H7NO

M = 1260.55

Triclinic,

a = 8.4939 (3) Å

b = 12.5451 (6) Å

c = 14.6717 (6) Å

α = 81.662 (2)°

β = 75.613 (1)°

γ = 79.442 (1)°

V = 1480.56 (11) Å3

Z = 1

Mo Kα radiation

μ = 0.72 mm−1

T = 293 K

0.40 × 0.25 × 0.20 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2004 ▶) T min = 0.763, T max = 0.870

11081 measured reflections

6571 independent reflections 6785

4713 reflections with I > 2σ(I)

R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.138

S = 1.02

6785 reflections

383 parameters

H-atom parameters constrained

Δρmax = 0.44 e Å−3

Δρmin = −0.42 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: APEX2 and SAINT (Bruker, 2004 ▶); data reduction: SAINT and XPREP (Bruker, 2004 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶) and DIAMOND (Brandenburg, 2010 ▶); software used to prepare material for publication: SHELXL97 and publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536814010150/fj2672sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814010150/fj2672Isup2.hkl

CCDC reference: 1001219

Additional supporting information: crystallographic information; 3D view; checkCIF report

[Ni2(C21H15N3O5)2(H2O)4]·4C3H7NO	Z = 1
Mr = 1260.55	F(000) = 660
Triclinic, P1	Dx = 1.414 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.4939 (3) Å	Cell parameters from 3205 reflections
b = 12.5451 (6) Å	θ = 2.9–26.1°
c = 14.6717 (6) Å	µ = 0.72 mm−1
α = 81.662 (2)°	T = 293 K
β = 75.613 (1)°	Block, brown
γ = 79.442 (1)°	0.40 × 0.25 × 0.20 mm
V = 1480.56 (11) Å3

Bruker Kappa APEXII CCD diffractometer	6571 independent reflections
Radiation source: fine-focus sealed tube	4713 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.025
Detector resolution: 8.33 pixels mm-1	θmax = 27.5°, θmin = 2.6°
ω and φ scan	h = −11→6
Absorption correction: multi-scan (SADABS; Bruker, 2004)	k = −16→16
Tmin = 0.763, Tmax = 0.870	l = −19→16
11081 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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.138	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.0721P)2 + 0.2776P] where P = (Fo2 + 2Fc2)/3
6785 reflections	(Δ/σ)max = 0.001
383 parameters	Δρmax = 0.44 e Å−3
0 restraints	Δρmin = −0.42 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	0.32132 (3)	0.56165 (3)	0.52457 (2)	0.03177 (13)
O1	0.47991 (19)	0.48838 (15)	0.41614 (12)	0.0316 (4)
O2	0.6760 (3)	0.3770 (3)	0.10470 (16)	0.0811 (10)
O3	0.1376 (2)	0.64291 (17)	0.61866 (14)	0.0427 (5)
O4	−0.5294 (5)	0.9447 (4)	0.8836 (3)	0.1297 (16)
O5	−0.6793 (4)	0.9197 (3)	0.7950 (3)	0.1240 (15)
O6	0.3857 (4)	0.7887 (3)	0.2882 (2)	0.0846 (9)
O7	0.3202 (5)	0.8970 (3)	0.5412 (3)	0.1077 (12)
O1W	0.4206 (2)	0.70844 (16)	0.46434 (15)	0.0427 (5)
H11	0.4496	0.7089	0.4052	0.064*
H12	0.3486	0.7627	0.4783	0.064*
O2W	0.2508 (2)	0.40630 (17)	0.58160 (14)	0.0418 (5)
H21	0.3131	0.3740	0.6167	0.063*
H22	0.2585	0.3688	0.5372	0.063*
N1	0.1453 (2)	0.59582 (18)	0.45394 (15)	0.0317 (5)
N2	−0.0044 (2)	0.65070 (19)	0.50159 (16)	0.0342 (5)
N3	−0.5476 (4)	0.9086 (3)	0.8164 (3)	0.0864 (12)
N4	0.4309 (4)	0.7733 (3)	0.1324 (2)	0.0737 (9)
N5	0.1458 (6)	1.0356 (3)	0.6066 (3)	0.1009 (15)
C1	0.4525 (3)	0.4821 (2)	0.33231 (18)	0.0318 (6)
C2	0.5816 (3)	0.4342 (3)	0.2632 (2)	0.0423 (7)
H2	0.6845	0.4099	0.2766	0.051*
C3	0.5579 (4)	0.4229 (3)	0.1763 (2)	0.0557 (10)
C4	0.4067 (4)	0.4603 (3)	0.1528 (2)	0.0636 (11)
H4	0.3913	0.4531	0.0935	0.076*
C5	0.2821 (4)	0.5078 (3)	0.2195 (2)	0.0536 (9)
H5	0.1808	0.5328	0.2043	0.064*
C6	0.2981 (3)	0.5210 (2)	0.30952 (19)	0.0353 (6)
C7	0.1548 (3)	0.5754 (2)	0.37016 (19)	0.0360 (6)
H7	0.0612	0.5976	0.3460	0.043*
C8	0.8333 (4)	0.3326 (4)	0.1248 (3)	0.0764 (14)
H8A	0.8215	0.2755	0.1772	0.092*
H8B	0.8817	0.3890	0.1418	0.092*
C9	0.9403 (4)	0.2870 (4)	0.0367 (3)	0.0756 (13)
C10	1.0033 (5)	0.1770 (4)	0.0401 (3)	0.0836 (14)
H10	0.9775	0.1317	0.0960	0.100*
C11	1.1050 (5)	0.1345 (5)	−0.0403 (4)	0.1038 (19)
H11A	1.1476	0.0607	−0.0388	0.125*
C12	1.1420 (5)	0.2034 (6)	−0.1226 (4)	0.117 (2)
H12A	1.2106	0.1747	−0.1762	0.141*
C13	1.0813 (6)	0.3122 (6)	−0.1277 (3)	0.119 (2)
H13	1.1064	0.3569	−0.1840	0.143*
C14	0.9792 (5)	0.3550 (5)	−0.0451 (3)	0.107 (2)
H14	0.9385	0.4291	−0.0463	0.128*
C15	0.0093 (3)	0.6707 (2)	0.5843 (2)	0.0341 (6)
C16	−0.1380 (3)	0.7329 (3)	0.6438 (2)	0.0400 (7)
C17	−0.2891 (4)	0.7543 (3)	0.6213 (3)	0.0636 (11)
H17	−0.3014	0.7294	0.5672	0.076*
C18	−0.4227 (4)	0.8118 (4)	0.6775 (3)	0.0750 (13)
H18	−0.5244	0.8258	0.6615	0.090*
C19	−0.4044 (4)	0.8476 (3)	0.7558 (2)	0.0592 (10)
C20	−0.2586 (5)	0.8284 (4)	0.7814 (3)	0.0735 (12)
H20	−0.2484	0.8538	0.8358	0.088*
C21	−0.1248 (4)	0.7701 (3)	0.7250 (2)	0.0640 (11)
H21A	−0.0242	0.7558	0.7422	0.077*
C22	0.4572 (5)	0.7448 (4)	0.2167 (3)	0.0716 (11)
H22A	0.5382	0.6853	0.2235	0.086*
C23	0.3069 (8)	0.8619 (6)	0.1161 (4)	0.140 (3)
H23A	0.2534	0.8919	0.1745	0.209*
H23B	0.2276	0.8364	0.0914	0.209*
H23C	0.3560	0.9170	0.0714	0.209*
C24	0.5236 (7)	0.7171 (5)	0.0517 (3)	0.1112 (18)
H24A	0.5928	0.6536	0.0726	0.167*
H24B	0.5903	0.7649	0.0082	0.167*
H24C	0.4490	0.6955	0.0208	0.167*
C25	0.1844 (8)	0.9403 (5)	0.5711 (5)	0.117 (2)
H25	0.0983	0.9047	0.5696	0.140*
C26	0.2699 (10)	1.0969 (5)	0.6094 (5)	0.154 (3)
H26A	0.3686	1.0741	0.5638	0.231*
H26B	0.2919	1.0848	0.6715	0.231*
H26C	0.2327	1.1731	0.5948	0.231*
C27	−0.0180 (10)	1.0771 (7)	0.6473 (7)	0.231 (6)
H27A	−0.0907	1.0479	0.6201	0.347*
H27B	−0.0347	1.1551	0.6353	0.347*
H27C	−0.0405	1.0565	0.7143	0.347*

	U11	U22	U33	U12	U13	U23
Ni1	0.01855 (17)	0.0461 (2)	0.0311 (2)	0.00660 (13)	−0.00672 (12)	−0.01827 (16)
O1	0.0220 (8)	0.0457 (11)	0.0290 (9)	0.0055 (7)	−0.0087 (7)	−0.0184 (8)
O2	0.0481 (13)	0.146 (3)	0.0468 (14)	0.0433 (15)	−0.0216 (11)	−0.0589 (16)
O3	0.0269 (9)	0.0638 (14)	0.0375 (11)	0.0146 (9)	−0.0110 (8)	−0.0266 (10)
O4	0.112 (3)	0.172 (4)	0.078 (2)	0.064 (3)	0.000 (2)	−0.070 (3)
O5	0.0563 (18)	0.172 (4)	0.112 (3)	0.052 (2)	0.0070 (18)	−0.047 (3)
O6	0.102 (2)	0.088 (2)	0.0554 (17)	−0.0048 (17)	−0.0103 (16)	−0.0082 (16)
O7	0.107 (3)	0.082 (2)	0.141 (3)	0.0190 (19)	−0.040 (2)	−0.057 (2)
O1W	0.0339 (9)	0.0425 (12)	0.0517 (13)	0.0051 (8)	−0.0118 (9)	−0.0151 (10)
O2W	0.0310 (9)	0.0549 (13)	0.0406 (11)	−0.0009 (9)	−0.0097 (8)	−0.0127 (10)
N1	0.0199 (9)	0.0416 (13)	0.0329 (12)	0.0058 (9)	−0.0055 (8)	−0.0154 (10)
N2	0.0183 (9)	0.0465 (14)	0.0357 (13)	0.0085 (9)	−0.0059 (9)	−0.0154 (11)
N3	0.068 (2)	0.098 (3)	0.063 (2)	0.040 (2)	0.0104 (18)	−0.018 (2)
N4	0.077 (2)	0.086 (3)	0.059 (2)	−0.0139 (19)	−0.0130 (17)	−0.0139 (19)
N5	0.122 (3)	0.056 (2)	0.092 (3)	0.019 (2)	0.013 (3)	−0.009 (2)
C1	0.0273 (12)	0.0396 (16)	0.0297 (14)	0.0007 (11)	−0.0080 (10)	−0.0129 (12)
C2	0.0291 (13)	0.062 (2)	0.0350 (15)	0.0114 (13)	−0.0103 (11)	−0.0213 (14)
C3	0.0397 (16)	0.090 (3)	0.0365 (17)	0.0191 (16)	−0.0108 (13)	−0.0355 (18)
C4	0.0478 (17)	0.105 (3)	0.0419 (18)	0.0241 (18)	−0.0237 (14)	−0.041 (2)
C5	0.0361 (15)	0.085 (3)	0.0425 (18)	0.0159 (15)	−0.0205 (13)	−0.0292 (18)
C6	0.0293 (12)	0.0473 (17)	0.0312 (14)	0.0022 (11)	−0.0098 (11)	−0.0154 (13)
C7	0.0231 (12)	0.0492 (18)	0.0375 (15)	0.0063 (11)	−0.0126 (11)	−0.0153 (13)
C8	0.0428 (18)	0.128 (4)	0.055 (2)	0.037 (2)	−0.0175 (16)	−0.050 (2)
C9	0.0441 (18)	0.130 (4)	0.052 (2)	0.030 (2)	−0.0181 (16)	−0.050 (2)
C10	0.052 (2)	0.113 (4)	0.084 (3)	0.016 (2)	−0.007 (2)	−0.054 (3)
C11	0.062 (3)	0.133 (5)	0.117 (4)	0.017 (3)	−0.006 (3)	−0.081 (4)
C12	0.055 (3)	0.209 (7)	0.091 (4)	0.021 (3)	−0.006 (3)	−0.098 (5)
C13	0.076 (3)	0.200 (7)	0.067 (3)	0.041 (4)	−0.012 (2)	−0.052 (4)
C14	0.075 (3)	0.167 (5)	0.064 (3)	0.054 (3)	−0.020 (2)	−0.049 (3)
C15	0.0235 (12)	0.0398 (16)	0.0362 (15)	0.0016 (11)	−0.0006 (11)	−0.0135 (12)
C16	0.0293 (13)	0.0493 (18)	0.0359 (16)	0.0061 (12)	−0.0020 (11)	−0.0111 (14)
C17	0.0347 (15)	0.094 (3)	0.060 (2)	0.0211 (17)	−0.0116 (15)	−0.040 (2)
C18	0.0344 (16)	0.109 (3)	0.073 (3)	0.0261 (19)	−0.0099 (16)	−0.034 (2)
C19	0.0442 (17)	0.068 (2)	0.047 (2)	0.0218 (16)	0.0072 (15)	−0.0148 (18)
C20	0.067 (2)	0.096 (3)	0.049 (2)	0.025 (2)	−0.0089 (18)	−0.036 (2)
C21	0.0402 (17)	0.093 (3)	0.054 (2)	0.0248 (17)	−0.0123 (15)	−0.032 (2)
C22	0.073 (3)	0.071 (3)	0.069 (3)	−0.016 (2)	−0.012 (2)	−0.001 (2)
C23	0.138 (5)	0.181 (7)	0.083 (4)	0.036 (5)	−0.040 (4)	−0.012 (4)
C24	0.130 (4)	0.131 (5)	0.070 (3)	−0.017 (4)	−0.006 (3)	−0.035 (3)
C25	0.102 (4)	0.094 (4)	0.150 (6)	0.002 (3)	−0.032 (4)	−0.015 (4)
C26	0.242 (9)	0.095 (5)	0.125 (6)	−0.042 (5)	−0.029 (6)	−0.015 (4)
C27	0.173 (8)	0.199 (9)	0.211 (10)	0.069 (7)	0.072 (7)	0.010 (7)

Ni1—N1	1.974 (2)	C8—C9	1.505 (4)
Ni1—O1	2.0237 (16)	C8—H8A	0.9700
Ni1—O3	2.0335 (17)	C8—H8B	0.9700
Ni1—O1i	2.0456 (16)	C9—C14	1.374 (7)
Ni1—O2W	2.136 (2)	C9—C10	1.383 (6)
Ni1—O1W	2.147 (2)	C10—C11	1.389 (6)
O1—C1	1.323 (3)	C10—H10	0.9300
O1—Ni1i	2.0456 (16)	C11—C12	1.383 (8)
O2—C3	1.372 (3)	C11—H11A	0.9300
O2—C8	1.434 (4)	C12—C13	1.366 (8)
O3—C15	1.282 (3)	C12—H12A	0.9300
O4—N3	1.197 (5)	C13—C14	1.416 (6)
O5—N3	1.215 (5)	C13—H13	0.9300
O6—C22	1.225 (5)	C14—H14	0.9300
O7—C25	1.186 (6)	C15—C16	1.494 (3)
O1W—H11	0.8400	C16—C17	1.373 (4)
O1W—H12	0.8400	C16—C21	1.377 (5)
O2W—H21	0.8400	C17—C18	1.377 (4)
O2W—H22	0.8400	C17—H17	0.9300
N1—C7	1.272 (3)	C18—C19	1.345 (5)
N1—N2	1.399 (3)	C18—H18	0.9300
N2—C15	1.311 (3)	C19—C20	1.352 (5)
N3—C19	1.474 (4)	C20—C21	1.384 (4)
N4—C22	1.299 (5)	C20—H20	0.9300
N4—C23	1.421 (6)	C21—H21A	0.9300
N4—C24	1.447 (5)	C22—H22A	0.9300
N5—C25	1.326 (7)	C23—H23A	0.9600
N5—C27	1.405 (7)	C23—H23B	0.9600
N5—C26	1.426 (8)	C23—H23C	0.9600
C1—C2	1.405 (3)	C24—H24A	0.9600
C1—C6	1.417 (3)	C24—H24B	0.9600
C2—C3	1.369 (4)	C24—H24C	0.9600
C2—H2	0.9300	C25—H25	0.9300
C3—C4	1.393 (4)	C26—H26A	0.9600
C4—C5	1.363 (4)	C26—H26B	0.9600
C4—H4	0.9300	C26—H26C	0.9600
C5—C6	1.396 (4)	C27—H27A	0.9600
C5—H5	0.9300	C27—H27B	0.9600
C6—C7	1.440 (3)	C27—H27C	0.9600
C7—H7	0.9300
N1—Ni1—O1	91.70 (8)	C10—C9—C8	119.3 (4)
N1—Ni1—O3	79.10 (8)	C9—C10—C11	119.8 (5)
O1—Ni1—O3	170.70 (7)	C9—C10—H10	120.1
N1—Ni1—O1i	171.98 (7)	C11—C10—H10	120.1
O1—Ni1—O1i	80.54 (7)	C12—C11—C10	119.1 (5)
O3—Ni1—O1i	108.71 (7)	C12—C11—H11A	120.4
N1—Ni1—O2W	91.81 (9)	C10—C11—H11A	120.4
O1—Ni1—O2W	88.30 (7)	C13—C12—C11	122.2 (4)
O3—Ni1—O2W	93.27 (8)	C13—C12—H12A	118.9
O1i—Ni1—O2W	85.99 (7)	C11—C12—H12A	118.9
N1—Ni1—O1W	92.89 (9)	C12—C13—C14	118.3 (6)
O1—Ni1—O1W	87.03 (8)	C12—C13—H13	120.9
O3—Ni1—O1W	92.07 (8)	C14—C13—H13	120.9
O1i—Ni1—O1W	88.74 (7)	C9—C14—C13	120.0 (5)
O2W—Ni1—O1W	173.47 (7)	C9—C14—H14	120.0
C1—O1—Ni1	126.65 (14)	C13—C14—H14	120.0
C1—O1—Ni1i	133.85 (14)	O3—C15—N2	126.2 (2)
Ni1—O1—Ni1i	99.46 (7)	O3—C15—C16	116.9 (2)
C3—O2—C8	117.0 (2)	N2—C15—C16	116.9 (2)
C15—O3—Ni1	109.58 (16)	C17—C16—C21	117.7 (3)
Ni1—O1W—H11	109.5	C17—C16—C15	122.6 (3)
Ni1—O1W—H12	109.5	C21—C16—C15	119.7 (2)
H11—O1W—H12	109.5	C16—C17—C18	121.3 (3)
Ni1—O2W—H21	109.5	C16—C17—H17	119.4
Ni1—O2W—H22	109.5	C18—C17—H17	119.4
H21—O2W—H22	109.5	C19—C18—C17	119.2 (3)
C7—N1—N2	117.2 (2)	C19—C18—H18	120.4
C7—N1—Ni1	127.20 (16)	C17—C18—H18	120.4
N2—N1—Ni1	115.54 (16)	C18—C19—C20	122.0 (3)
C15—N2—N1	109.52 (19)	C18—C19—N3	119.2 (3)
O4—N3—O5	123.2 (3)	C20—C19—N3	118.8 (4)
O4—N3—C19	119.1 (4)	C19—C20—C21	118.6 (4)
O5—N3—C19	117.7 (4)	C19—C20—H20	120.7
C22—N4—C23	120.6 (4)	C21—C20—H20	120.7
C22—N4—C24	122.3 (4)	C16—C21—C20	121.2 (3)
C23—N4—C24	117.1 (4)	C16—C21—H21A	119.4
C25—N5—C27	121.3 (7)	C20—C21—H21A	119.4
C25—N5—C26	121.2 (5)	O6—C22—N4	126.3 (4)
C27—N5—C26	117.5 (6)	O6—C22—H22A	116.8
O1—C1—C2	118.7 (2)	N4—C22—H22A	116.8
O1—C1—C6	122.7 (2)	N4—C23—H23A	109.5
C2—C1—C6	118.6 (2)	N4—C23—H23B	109.5
C3—C2—C1	120.8 (2)	H23A—C23—H23B	109.5
C3—C2—H2	119.6	N4—C23—H23C	109.5
C1—C2—H2	119.6	H23A—C23—H23C	109.5
C2—C3—O2	125.0 (3)	H23B—C23—H23C	109.5
C2—C3—C4	121.4 (3)	N4—C24—H24A	109.5
O2—C3—C4	113.7 (3)	N4—C24—H24B	109.5
C5—C4—C3	117.8 (3)	H24A—C24—H24B	109.5
C5—C4—H4	121.1	N4—C24—H24C	109.5
C3—C4—H4	121.1	H24A—C24—H24C	109.5
C4—C5—C6	123.6 (3)	H24B—C24—H24C	109.5
C4—C5—H5	118.2	O7—C25—N5	125.0 (6)
C6—C5—H5	118.2	O7—C25—H25	117.5
C5—C6—C1	117.8 (2)	N5—C25—H25	117.5
C5—C6—C7	116.1 (2)	N5—C26—H26A	109.5
C1—C6—C7	126.0 (2)	N5—C26—H26B	109.5
N1—C7—C6	125.6 (2)	H26A—C26—H26B	109.5
N1—C7—H7	117.2	N5—C26—H26C	109.5
C6—C7—H7	117.2	H26A—C26—H26C	109.5
O2—C8—C9	107.1 (3)	H26B—C26—H26C	109.5
O2—C8—H8A	110.3	N5—C27—H27A	109.5
C9—C8—H8A	110.3	N5—C27—H27B	109.5
O2—C8—H8B	110.3	H27A—C27—H27B	109.5
C9—C8—H8B	110.3	N5—C27—H27C	109.5
H8A—C8—H8B	108.5	H27A—C27—H27C	109.5
C14—C9—C10	120.6 (4)	H27B—C27—H27C	109.5
C14—C9—C8	120.0 (4)
N1—Ni1—O1—C1	3.8 (2)	N2—N1—C7—C6	179.3 (3)
O1i—Ni1—O1—C1	−178.2 (3)	Ni1—N1—C7—C6	0.9 (4)
O2W—Ni1—O1—C1	95.6 (2)	C5—C6—C7—N1	−179.4 (3)
O1W—Ni1—O1—C1	−89.0 (2)	C1—C6—C7—N1	−0.7 (5)
N1—Ni1—O1—Ni1i	−177.97 (9)	C3—O2—C8—C9	179.7 (4)
O1i—Ni1—O1—Ni1i	0.0	O2—C8—C9—C14	62.8 (5)
O2W—Ni1—O1—Ni1i	−86.21 (8)	O2—C8—C9—C10	−119.4 (4)
O1W—Ni1—O1—Ni1i	89.22 (8)	C14—C9—C10—C11	−0.9 (7)
N1—Ni1—O3—C15	0.94 (19)	C8—C9—C10—C11	−178.6 (4)
O1i—Ni1—O3—C15	−177.14 (18)	C9—C10—C11—C12	0.2 (7)
O2W—Ni1—O3—C15	−90.27 (19)	C10—C11—C12—C13	−0.3 (8)
O1W—Ni1—O3—C15	93.49 (19)	C11—C12—C13—C14	1.0 (8)
O1—Ni1—N1—C7	−2.0 (3)	C10—C9—C14—C13	1.6 (7)
O3—Ni1—N1—C7	176.7 (3)	C8—C9—C14—C13	179.3 (4)
O2W—Ni1—N1—C7	−90.3 (3)	C12—C13—C14—C9	−1.6 (8)
O1W—Ni1—N1—C7	85.2 (3)	Ni1—O3—C15—N2	0.0 (4)
O1—Ni1—N1—N2	179.60 (17)	Ni1—O3—C15—C16	−179.2 (2)
O3—Ni1—N1—N2	−1.74 (17)	N1—N2—C15—O3	−1.5 (4)
O2W—Ni1—N1—N2	91.25 (18)	N1—N2—C15—C16	177.8 (2)
O1W—Ni1—N1—N2	−93.29 (18)	O3—C15—C16—C17	−170.8 (3)
C7—N1—N2—C15	−176.4 (3)	N2—C15—C16—C17	9.9 (5)
Ni1—N1—N2—C15	2.2 (3)	O3—C15—C16—C21	8.6 (5)
Ni1—O1—C1—C2	175.7 (2)	N2—C15—C16—C21	−170.7 (3)
Ni1i—O1—C1—C2	−1.8 (4)	C21—C16—C17—C18	0.6 (6)
Ni1—O1—C1—C6	−4.7 (4)	C15—C16—C17—C18	−180.0 (3)
Ni1i—O1—C1—C6	177.80 (19)	C16—C17—C18—C19	0.0 (7)
O1—C1—C2—C3	178.1 (3)	C17—C18—C19—C20	−0.2 (7)
C6—C1—C2—C3	−1.6 (5)	C17—C18—C19—N3	−179.6 (4)
C1—C2—C3—O2	−179.7 (3)	O4—N3—C19—C18	−176.6 (5)
C1—C2—C3—C4	1.3 (6)	O5—N3—C19—C18	3.4 (6)
C8—O2—C3—C2	3.4 (6)	O4—N3—C19—C20	4.0 (7)
C8—O2—C3—C4	−177.6 (4)	O5—N3—C19—C20	−176.0 (4)
C2—C3—C4—C5	−0.6 (6)	C18—C19—C20—C21	0.0 (7)
O2—C3—C4—C5	−179.6 (4)	N3—C19—C20—C21	179.3 (4)
C3—C4—C5—C6	0.1 (6)	C17—C16—C21—C20	−0.9 (6)
C4—C5—C6—C1	−0.4 (5)	C15—C16—C21—C20	179.7 (3)
C4—C5—C6—C7	178.5 (4)	C19—C20—C21—C16	0.6 (7)
O1—C1—C6—C5	−178.6 (3)	C23—N4—C22—O6	−1.4 (8)
C2—C1—C6—C5	1.1 (4)	C24—N4—C22—O6	179.2 (4)
O1—C1—C6—C7	2.7 (5)	C27—N5—C25—O7	−175.0 (7)
C2—C1—C6—C7	−177.6 (3)	C26—N5—C25—O7	1.6 (10)

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H11···O6	0.84	2.00	2.702 (4)	140
O1W—H12···O7	0.84	1.98	2.674 (4)	139
O2W—H21···O1Wi	0.84	2.40	2.862 (2)	115
O2W—H22···N2ii	0.84	2.43	2.908 (3)	117
C2—H2···O3i	0.93	2.36	3.217 (3)	153
C18—H18···O7iii	0.93	2.43	3.257 (6)	147
C26—H26B···O5iv	0.96	2.56	3.320 (8)	136
C22—H22A···Cg4	0.93	2.95	3.440 (5)	115
C23—H23B···Cg5v	0.96	2.94	3.89 (8)	172

Table 1

Hydrogen-bond geometry (Å, °)

Cg4 and Cg5 are the centroids of the C1–C6 and C9–C14 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H11⋯O6	0.84	2.00	2.702 (4)	140
O1W—H12⋯O7	0.84	1.98	2.674 (4)	139
O2W—H21⋯O1W i	0.84	2.40	2.862 (2)	115
O2W—H22⋯N2ii	0.84	2.43	2.908 (3)	117
C2—H2⋯O3i	0.93	2.36	3.217 (3)	153
C18—H18⋯O7iii	0.93	2.43	3.257 (6)	147
C26—H26B⋯O5iv	0.96	2.56	3.320 (8)	136
C22—H22A⋯Cg4	0.93	2.95	3.440 (5)	115
C23—H23B⋯Cg5v	0.96	2.94	3.89 (8)	172

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