[N,N,N′,N′-Tetra­kis(benzimidazol-2-ylmethyl)ethane-1,2-diamine]nickel(II) dinitrate methanol solvate

In the title complex, [Ni(EDTB)](NO₃)₂·CH₃OH [EDTB is N,N,N′,N′-tetra­kis(benzimidazol-2-ylmeth­yl)ethane-1,2-diamine, C₃₄H₃₂N₁₀], the Ni^II ion is coordinated by six N atoms of the EDTB ligand to form a distorted octa­hedral geometry. The crystal packing is stabilized by inter­molecular N—H...O, N—H...N and O—H...O hydrogen bonds.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.044
• wR factor = 0.119
• Data-to-parameter ratio = 14.8

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature .        293 K
PLAT244_ALERT_4_C Low   'Solvent' Ueq as Compared to Neighbors for        N11
PLAT244_ALERT_4_C Low   'Solvent' Ueq as Compared to Neighbors for        N12
PLAT601_ALERT_2_C Structure Contains Solvent Accessible VOIDS of .      55.00 A   3  

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   7 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   4 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion

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S1. Comment

Some benzimidazole derivatives can be used as building blocks in the synthesis of model complexes (Ogawa et al., 1998; Liu et al., 2002; Blackburn et al., 1989; Plengea et al., 2003). The hexadentate polyfunctional benzimidazole ligand EDTB [EDTB is N,N,N',N'-tetrakis(2-benzimidazolylmethyl)-1,2-ethanediamine] has attracted considerable attention in recent years, and a series of compounds containing this ligand have been reported. Among these, [Mn(EDTB)(Ac)](Ac)·C₂H₅OH (Liao et al., 2001) shows SOD-like activity, while Cu(EDTB)(NO₃)₂·C₂H₅OH (Chen et al., 2004) exhibits catecholase-like activity. As an extension of this work, we have synthesized the title compound, (I), and report its crystal structure here.

The asymmetric unit of (I) consists of an [Ni(EDTB)]²⁺ cation, two NO₃⁻ anions and a methanol molecule (Fig. 1). Selected bond lengths and angles are listed in Table 1. The Ni^II ion is six-coordinated by four benzimidazole and two amino N atoms, forming a distorted octahedral geometry. The equatorial plane is made up by the N atoms of two benzimidazole groups [Ni—N1 = 2.046 (2) Å and Ni—N7 = 2.095 (2) Å] and two amino N atoms [Ni—N3 = 2.186 (2) Å and Ni—N6 = 2.137 (2) Å], while the axial positions are occupied the N atoms of the other two benzimidazole groups [Ni—N4 = 2.094 (2) Å and Ni—N9 = 2.098 (2) Å]. The N4—Ni1—N9 angle is 171.40 (8)°, and the Ni atom is displaced by 0.023 (5) Å from the equatorial plane. The crystal packing is stabilized by intermolecular N—H···O, N—H···N and O—H···O hydrogen bonds (Table 2).

S2. Experimental

EDTB was prepared as described previously by Gomez-Romero et al. (1990). EDTB (1 mmol) was dissolved in hot methanol (15 ml) and a solution of Ni(NO₃)₂·6H₂O (1 mmol) in water (10 ml) was added dropwise. The mixture was filtered after continuous stirring for 3 h. Violet single crystals of (I) suitable for X-ray analysis were obtained by slow evaporation of the solution at room temperature over a week. Analysis calculated for C₃₅H₃₆N₁₂NiO₇: C 56.55, H 4.34, N 22.61%; found: C 57.46,H 4.52,N 23.02%.

S3. Refinement

All H atoms were placed in calculated positions, with C—H = 0.86 [0.93 in CIF?]–0.97 Å, O—H = 0.82 Å and N—H = 0.86 Å, and included in the final cycles of refinement using a riding model, with U_iso(H) = 1.2 or 1.5 times U_eq(parent atom).

Computing details

Data collection: SMART-NT (Bruker, 1998); cell refinement: SAINT-NT (Bruker, 1998); data reduction: SAINT-NT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL-NT (Bruker, 1998); software used to prepare material for publication: SHELXTL-NT.

Figures

Fig. 1. The asymmetric unit of the title compound, with 30% probability displacement ellipsoids. H atoms have been omitted for clarity.

[N,N,N',N'-Tetrakis(benzimidazol-2-ylmethyl)ethane-1,2-diamine]nickel(II) dinitrate methanol solvate

Crystal data

[nI(C34H32N10)](NO3)2·CH4O	Z = 2
Mr = 795.47	F(000) = 828
Triclinic, P1	Dx = 1.452 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 11.718 (4) Å	Cell parameters from 875 reflections
b = 12.103 (4) Å	θ = 3.3–25.0°
c = 14.528 (5) Å	µ = 0.60 mm^−1
α = 91.409 (5)°	T = 293 K
β = 103.988 (5)°	Prism, violet
γ = 113.291 (5)°	0.22 × 0.18 × 0.14 mm
V = 1819.6 (10) Å^3

Data collection

Bruker SMART CCD area-detector diffractometer	7392 independent reflections
Radiation source: fine-focus sealed tube	5192 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.026
ϕ and ω scans	θmax = 26.4°, θmin = 1.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −14→14
Tmin = 0.878, Tmax = 0.919	k = −15→14
10574 measured reflections	l = −18→17

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.119	H-atom parameters constrained
S = 1.02	w = 1/[σ^2(Fo^2) + (0.0602P)^2] where P = (Fo^2 + 2Fc^2)/3
7392 reflections	(Δ/σ)max = 0.001
498 parameters	Δρmax = 0.43 e Å^−3
0 restraints	Δρmin = −0.38 e Å^−3

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Ni1	0.61558 (3)	0.80491 (3)	0.71156 (2)	0.03094 (12)
N1	0.4779 (2)	0.8354 (2)	0.75831 (15)	0.0327 (5)
N2	0.3189 (2)	0.8955 (2)	0.72042 (16)	0.0418 (6)
H2	0.2631	0.9182	0.6863	0.050*
N3	0.4702 (2)	0.7759 (2)	0.57592 (15)	0.0362 (5)
N4	0.5047 (2)	0.6186 (2)	0.70359 (16)	0.0372 (5)
N5	0.3081 (2)	0.4705 (2)	0.64662 (17)	0.0430 (6)
H5A	0.2323	0.4296	0.6088	0.052*
N6	0.7271 (2)	0.7847 (2)	0.62101 (15)	0.0376 (5)
N7	0.7741 (2)	0.7993 (2)	0.81237 (15)	0.0355 (5)
N8	0.9139 (2)	0.7142 (2)	0.83320 (18)	0.0472 (6)
H8	0.9571	0.6759	0.8195	0.057*
N9	0.7136 (2)	0.9882 (2)	0.69742 (15)	0.0334 (5)
N10	0.8568 (2)	1.1200 (2)	0.63321 (16)	0.0412 (6)
H10	0.9157	1.1478	0.6038	0.049*
C1	0.4165 (3)	0.8654 (3)	0.58962 (18)	0.0393 (7)
H1A	0.3330	0.8427	0.5437	0.047*
H1B	0.4740	0.9455	0.5808	0.047*
C2	0.4031 (3)	0.8658 (2)	0.68985 (19)	0.0347 (6)
C3	0.3372 (3)	0.8834 (3)	0.8164 (2)	0.0379 (7)
C4	0.2765 (3)	0.8989 (3)	0.8836 (2)	0.0491 (8)
H4	0.2103	0.9250	0.8681	0.059*
C5	0.3189 (3)	0.8740 (3)	0.9740 (2)	0.0524 (8)
H5	0.2813	0.8848	1.0211	0.063*
C6	0.4172 (3)	0.8327 (3)	0.9974 (2)	0.0482 (8)
H6	0.4425	0.8161	1.0593	0.058*
C7	0.4769 (3)	0.8162 (3)	0.93121 (19)	0.0397 (7)
H7	0.5411	0.7876	0.9467	0.048*
C8	0.4374 (3)	0.8442 (2)	0.83978 (19)	0.0338 (6)
C9	0.3667 (3)	0.6498 (3)	0.5575 (2)	0.0436 (7)
H9A	0.2842	0.6530	0.5533	0.052*
H9B	0.3611	0.6099	0.4968	0.052*
C10	0.3942 (3)	0.5787 (3)	0.63524 (19)	0.0365 (6)
C11	0.3633 (3)	0.4366 (3)	0.7298 (2)	0.0412 (7)
C12	0.3163 (3)	0.3379 (3)	0.7778 (2)	0.0575 (9)
H12	0.2339	0.2763	0.7538	0.069*
C13	0.3980 (4)	0.3358 (3)	0.8630 (3)	0.0603 (9)
H13	0.3699	0.2709	0.8972	0.072*
C14	0.5215 (3)	0.4278 (3)	0.8996 (2)	0.0527 (8)
H14	0.5734	0.4228	0.9574	0.063*
C15	0.5683 (3)	0.5257 (3)	0.8525 (2)	0.0445 (7)
H15	0.6508	0.5869	0.8774	0.053*
C16	0.4877 (3)	0.5300 (2)	0.7657 (2)	0.0365 (6)
C17	0.5443 (3)	0.7981 (3)	0.50338 (19)	0.0419 (7)
H17A	0.5929	0.8846	0.5055	0.050*
H17B	0.4853	0.7664	0.4399	0.050*
C18	0.6363 (3)	0.7356 (3)	0.52432 (19)	0.0451 (7)
H18A	0.5873	0.6489	0.5208	0.054*
H18B	0.6843	0.7490	0.4768	0.054*
C19	0.7813 (3)	0.7001 (3)	0.6653 (2)	0.0459 (8)
H19A	0.7162	0.6172	0.6497	0.055*
H19B	0.8539	0.7049	0.6421	0.055*
C20	0.8240 (3)	0.7378 (3)	0.7707 (2)	0.0385 (7)
C21	0.9243 (3)	0.7629 (3)	0.9237 (2)	0.0431 (7)
C22	0.9982 (3)	0.7635 (3)	1.0147 (2)	0.0587 (9)
H22	1.0544	0.7254	1.0239	0.070*
C23	0.9846 (3)	0.8228 (4)	1.0900 (2)	0.0646 (10)
H23	1.0325	0.8246	1.1517	0.078*
C24	0.9013 (3)	0.8806 (3)	1.0769 (2)	0.0551 (9)
H24	0.8955	0.9208	1.1298	0.066*
C25	0.8272 (3)	0.8796 (3)	0.9873 (2)	0.0418 (7)
H25	0.7720	0.9187	0.9788	0.050*
C26	0.8376 (3)	0.8181 (2)	0.90997 (19)	0.0351 (6)
C27	0.8343 (3)	0.9041 (3)	0.6229 (2)	0.0407 (7)
H27A	0.9127	0.9099	0.6686	0.049*
H27B	0.8498	0.9108	0.5603	0.049*
C28	0.8016 (3)	1.0048 (3)	0.65025 (18)	0.0353 (6)
C29	0.8020 (3)	1.1857 (3)	0.67138 (19)	0.0386 (7)
C30	0.8225 (3)	1.3071 (3)	0.6754 (2)	0.0510 (8)
H30	0.8815	1.3619	0.6477	0.061*
C31	0.7511 (4)	1.3422 (3)	0.7225 (2)	0.0554 (9)
H31	0.7629	1.4230	0.7273	0.066*
C32	0.6613 (3)	1.2602 (3)	0.7632 (2)	0.0507 (8)
H32	0.6144	1.2877	0.7937	0.061*
C33	0.6401 (3)	1.1398 (3)	0.75960 (19)	0.0407 (7)
H33	0.5804	1.0858	0.7872	0.049*
C34	0.7122 (3)	1.1020 (2)	0.71255 (17)	0.0332 (6)
N11	0.0089 (3)	0.3620 (3)	0.4772 (2)	0.0530 (7)
O1	0.0971 (3)	0.4380 (2)	0.45105 (18)	0.0726 (7)
O2	−0.0999 (3)	0.3160 (3)	0.4240 (2)	0.1089 (11)
O3	0.0358 (3)	0.3350 (3)	0.5592 (2)	0.0800 (8)
N12	0.1501 (3)	0.0537 (3)	0.62839 (18)	0.0534 (7)
O4	0.1007 (3)	0.1209 (2)	0.59058 (17)	0.0694 (7)
O5	0.1351 (2)	0.0184 (3)	0.70521 (17)	0.0770 (8)
O6	0.2163 (3)	0.0215 (3)	0.58863 (18)	0.0862 (9)
O7	0.0475 (3)	0.6036 (3)	0.76333 (19)	0.0738 (7)
H7A	0.0500	0.6114	0.7079	0.111*
C35	0.1346 (4)	0.5554 (4)	0.8067 (4)	0.1025 (16)
H35A	0.2199	0.6077	0.8038	0.154*
H35B	0.1097	0.4763	0.7736	0.154*
H35C	0.1341	0.5492	0.8723	0.154*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Ni1	0.03129 (19)	0.0356 (2)	0.02798 (19)	0.01471 (15)	0.00984 (15)	0.00751 (14)
N1	0.0316 (12)	0.0382 (13)	0.0316 (12)	0.0156 (10)	0.0116 (10)	0.0112 (10)
N2	0.0342 (13)	0.0525 (16)	0.0422 (14)	0.0236 (12)	0.0066 (11)	0.0100 (12)
N3	0.0373 (13)	0.0414 (14)	0.0294 (12)	0.0157 (11)	0.0089 (10)	0.0072 (10)
N4	0.0383 (13)	0.0350 (13)	0.0377 (13)	0.0153 (11)	0.0090 (11)	0.0090 (11)
N5	0.0380 (13)	0.0375 (14)	0.0424 (14)	0.0069 (11)	0.0069 (12)	0.0035 (11)
N6	0.0440 (14)	0.0417 (14)	0.0312 (12)	0.0204 (12)	0.0132 (11)	0.0033 (11)
N7	0.0356 (13)	0.0406 (14)	0.0333 (12)	0.0182 (11)	0.0099 (11)	0.0077 (10)
N8	0.0442 (15)	0.0562 (17)	0.0539 (16)	0.0332 (13)	0.0135 (13)	0.0122 (13)
N9	0.0336 (12)	0.0397 (13)	0.0294 (12)	0.0150 (10)	0.0131 (10)	0.0073 (10)
N10	0.0356 (13)	0.0461 (15)	0.0383 (13)	0.0077 (11)	0.0192 (11)	0.0091 (11)
C1	0.0405 (16)	0.0467 (17)	0.0325 (15)	0.0205 (14)	0.0080 (13)	0.0137 (13)
C2	0.0292 (14)	0.0386 (16)	0.0364 (15)	0.0149 (12)	0.0078 (12)	0.0067 (13)
C3	0.0308 (15)	0.0412 (17)	0.0406 (16)	0.0130 (13)	0.0111 (13)	0.0032 (13)
C4	0.0391 (17)	0.055 (2)	0.059 (2)	0.0224 (15)	0.0183 (16)	0.0027 (16)
C5	0.053 (2)	0.061 (2)	0.0500 (19)	0.0224 (17)	0.0284 (17)	0.0045 (17)
C6	0.057 (2)	0.051 (2)	0.0389 (17)	0.0185 (16)	0.0232 (16)	0.0119 (15)
C7	0.0412 (16)	0.0456 (17)	0.0362 (15)	0.0190 (14)	0.0151 (13)	0.0124 (13)
C8	0.0296 (14)	0.0346 (15)	0.0379 (15)	0.0105 (12)	0.0149 (12)	0.0076 (12)
C9	0.0427 (17)	0.0444 (18)	0.0347 (16)	0.0122 (14)	0.0047 (14)	0.0045 (14)
C10	0.0355 (15)	0.0366 (16)	0.0340 (15)	0.0117 (13)	0.0094 (13)	0.0031 (13)
C11	0.0463 (17)	0.0368 (16)	0.0425 (17)	0.0176 (14)	0.0146 (15)	0.0064 (13)
C12	0.054 (2)	0.0401 (19)	0.071 (2)	0.0093 (16)	0.0204 (19)	0.0157 (17)
C13	0.065 (2)	0.049 (2)	0.069 (2)	0.0208 (18)	0.026 (2)	0.0308 (18)
C14	0.062 (2)	0.051 (2)	0.0482 (19)	0.0259 (18)	0.0153 (17)	0.0174 (16)
C15	0.0456 (17)	0.0370 (17)	0.0468 (18)	0.0149 (14)	0.0090 (15)	0.0101 (14)
C16	0.0400 (16)	0.0310 (15)	0.0401 (16)	0.0152 (13)	0.0129 (13)	0.0066 (13)
C17	0.0454 (17)	0.0522 (19)	0.0249 (14)	0.0164 (15)	0.0107 (13)	0.0069 (13)
C18	0.0545 (19)	0.0516 (19)	0.0303 (15)	0.0204 (16)	0.0165 (14)	0.0015 (14)
C19	0.0531 (19)	0.0508 (19)	0.0428 (17)	0.0311 (16)	0.0127 (15)	0.0026 (15)
C20	0.0346 (15)	0.0419 (17)	0.0452 (17)	0.0213 (13)	0.0118 (14)	0.0089 (14)
C21	0.0335 (16)	0.0493 (18)	0.0461 (18)	0.0170 (14)	0.0096 (14)	0.0119 (15)
C22	0.0384 (18)	0.076 (3)	0.060 (2)	0.0281 (18)	0.0032 (17)	0.0217 (19)
C23	0.049 (2)	0.089 (3)	0.0413 (19)	0.021 (2)	−0.0005 (17)	0.0139 (19)
C24	0.0463 (19)	0.070 (2)	0.0378 (17)	0.0130 (17)	0.0103 (15)	0.0065 (16)
C25	0.0364 (16)	0.0461 (18)	0.0384 (16)	0.0122 (14)	0.0104 (14)	0.0067 (14)
C26	0.0281 (14)	0.0357 (15)	0.0365 (15)	0.0087 (12)	0.0075 (12)	0.0076 (12)
C27	0.0376 (16)	0.0521 (19)	0.0355 (15)	0.0174 (14)	0.0174 (13)	0.0067 (14)
C28	0.0319 (14)	0.0435 (17)	0.0273 (14)	0.0111 (13)	0.0100 (12)	0.0050 (12)
C29	0.0382 (16)	0.0413 (17)	0.0308 (15)	0.0095 (13)	0.0117 (13)	0.0069 (13)
C30	0.058 (2)	0.0403 (18)	0.0450 (18)	0.0084 (15)	0.0179 (16)	0.0116 (15)
C31	0.073 (2)	0.0342 (18)	0.053 (2)	0.0170 (17)	0.0149 (18)	0.0042 (15)
C32	0.066 (2)	0.0470 (19)	0.0456 (18)	0.0268 (17)	0.0201 (17)	0.0036 (15)
C33	0.0472 (17)	0.0412 (17)	0.0361 (16)	0.0169 (14)	0.0176 (14)	0.0089 (13)
C34	0.0360 (15)	0.0360 (15)	0.0246 (13)	0.0123 (12)	0.0076 (12)	0.0043 (12)
N11	0.0452 (17)	0.0504 (18)	0.0631 (19)	0.0207 (14)	0.0137 (16)	−0.0047 (15)
O1	0.0745 (18)	0.0668 (17)	0.0691 (17)	0.0156 (14)	0.0302 (15)	0.0084 (13)
O2	0.0481 (17)	0.122 (3)	0.121 (3)	0.0246 (17)	−0.0162 (18)	−0.034 (2)
O3	0.0740 (18)	0.083 (2)	0.0782 (19)	0.0231 (15)	0.0262 (16)	0.0337 (16)
N12	0.0487 (16)	0.074 (2)	0.0416 (16)	0.0288 (15)	0.0139 (13)	0.0096 (14)
O4	0.0754 (17)	0.0917 (19)	0.0723 (16)	0.0584 (16)	0.0324 (14)	0.0275 (15)
O5	0.0619 (16)	0.128 (2)	0.0495 (14)	0.0403 (16)	0.0258 (13)	0.0337 (15)
O6	0.118 (2)	0.143 (3)	0.0644 (16)	0.105 (2)	0.0506 (17)	0.0467 (17)
O7	0.0801 (18)	0.0835 (19)	0.0766 (17)	0.0501 (16)	0.0268 (16)	0.0068 (16)
C35	0.076 (3)	0.090 (3)	0.141 (4)	0.050 (3)	0.002 (3)	−0.006 (3)

Geometric parameters (Å, º)

Ni1—N1	2.046 (2)	C12—C13	1.377 (4)
Ni1—N4	2.094 (2)	C12—H12	0.9300
Ni1—N7	2.095 (2)	C13—C14	1.393 (5)
Ni1—N9	2.098 (2)	C13—H13	0.9300
Ni1—N6	2.137 (2)	C14—C15	1.371 (4)
Ni1—N3	2.186 (2)	C14—H14	0.9300
N1—C2	1.321 (3)	C15—C16	1.397 (4)
N1—C8	1.394 (3)	C15—H15	0.9300
N2—C2	1.336 (3)	C17—C18	1.524 (4)
N2—C3	1.380 (3)	C17—H17A	0.9700
N2—H2	0.8600	C17—H17B	0.9700
N3—C1	1.482 (3)	C18—H18A	0.9700
N3—C17	1.486 (3)	C18—H18B	0.9700
N3—C9	1.494 (4)	C19—C20	1.488 (4)
N4—C10	1.325 (3)	C19—H19A	0.9700
N4—C16	1.404 (3)	C19—H19B	0.9700
N5—C10	1.345 (4)	C21—C22	1.393 (4)
N5—C11	1.380 (4)	C21—C26	1.402 (4)
N5—H5A	0.8600	C22—C23	1.368 (5)
N6—C18	1.482 (3)	C22—H22	0.9300
N6—C27	1.487 (4)	C23—C24	1.391 (5)
N6—C19	1.489 (3)	C23—H23	0.9300
N7—C20	1.325 (3)	C24—C25	1.376 (4)
N7—C26	1.399 (3)	C24—H24	0.9300
N8—C20	1.343 (3)	C25—C26	1.388 (4)
N8—C21	1.384 (4)	C25—H25	0.9300
N8—H8	0.8600	C27—C28	1.485 (4)
N9—C28	1.326 (3)	C27—H27A	0.9700
N9—C34	1.397 (3)	C27—H27B	0.9700
N10—C28	1.343 (3)	C29—C30	1.389 (4)
N10—C29	1.381 (4)	C29—C34	1.408 (4)
N10—H10	0.8600	C30—C31	1.376 (5)
C1—C2	1.502 (4)	C30—H30	0.9300
C1—H1A	0.9700	C31—C32	1.395 (5)
C1—H1B	0.9700	C31—H31	0.9300
C3—C4	1.388 (4)	C32—C33	1.375 (4)
C3—C8	1.406 (4)	C32—H32	0.9300
C4—C5	1.373 (4)	C33—C34	1.400 (4)
C4—H4	0.9300	C33—H33	0.9300
C5—C6	1.402 (4)	N11—O2	1.214 (3)
C5—H5	0.9300	N11—O1	1.230 (4)
C6—C7	1.371 (4)	N11—O3	1.243 (3)
C6—H6	0.9300	N12—O5	1.232 (3)
C7—C8	1.393 (4)	N12—O6	1.239 (3)
C7—H7	0.9300	N12—O4	1.240 (3)
C9—C10	1.487 (4)	O7—C35	1.399 (4)
C9—H9A	0.9700	O7—H7A	0.8200
C9—H9B	0.9700	C35—H35A	0.9600
C11—C12	1.386 (4)	C35—H35B	0.9600
C11—C16	1.406 (4)	C35—H35C	0.9600
N1—Ni1—N4	88.09 (9)	C11—C12—H12	121.7
N1—Ni1—N7	119.12 (9)	C12—C13—C14	122.0 (3)
N4—Ni1—N7	92.81 (9)	C12—C13—H13	119.0
N1—Ni1—N9	93.07 (9)	C14—C13—H13	119.0
N4—Ni1—N9	171.40 (8)	C15—C14—C13	121.7 (3)
N7—Ni1—N9	94.07 (9)	C15—C14—H14	119.2
N1—Ni1—N6	161.62 (8)	C13—C14—H14	119.2
N4—Ni1—N6	95.20 (9)	C14—C15—C16	117.5 (3)
N7—Ni1—N6	78.85 (9)	C14—C15—H15	121.2
N9—Ni1—N6	81.09 (9)	C16—C15—H15	121.2
N1—Ni1—N3	79.18 (9)	C15—C16—N4	131.2 (3)
N4—Ni1—N3	80.49 (9)	C15—C16—C11	120.2 (3)
N7—Ni1—N3	160.51 (9)	N4—C16—C11	108.6 (2)
N9—Ni1—N3	91.35 (8)	N3—C17—C18	109.3 (2)
N6—Ni1—N3	83.54 (9)	N3—C17—H17A	109.8
C2—N1—C8	105.4 (2)	C18—C17—H17A	109.8
C2—N1—Ni1	111.63 (17)	N3—C17—H17B	109.8
C8—N1—Ni1	142.81 (17)	C18—C17—H17B	109.8
C2—N2—C3	107.9 (2)	H17A—C17—H17B	108.3
C2—N2—H2	126.1	N6—C18—C17	109.9 (2)
C3—N2—H2	126.1	N6—C18—H18A	109.7
C1—N3—C17	115.4 (2)	C17—C18—H18A	109.7
C1—N3—C9	110.4 (2)	N6—C18—H18B	109.7
C17—N3—C9	111.6 (2)	C17—C18—H18B	109.7
C1—N3—Ni1	103.90 (15)	H18A—C18—H18B	108.2
C17—N3—Ni1	104.04 (16)	C20—C19—N6	106.8 (2)
C9—N3—Ni1	110.96 (16)	C20—C19—H19A	110.4
C10—N4—C16	105.3 (2)	N6—C19—H19A	110.4
C10—N4—Ni1	112.85 (17)	C20—C19—H19B	110.4
C16—N4—Ni1	137.56 (19)	N6—C19—H19B	110.4
C10—N5—C11	107.8 (2)	H19A—C19—H19B	108.6
C10—N5—H5A	126.1	N7—C20—N8	112.9 (3)
C11—N5—H5A	126.1	N7—C20—C19	121.9 (2)
C18—N6—C27	112.6 (2)	N8—C20—C19	125.2 (3)
C18—N6—C19	114.0 (2)	N8—C21—C22	133.0 (3)
C27—N6—C19	109.5 (2)	N8—C21—C26	105.6 (2)
C18—N6—Ni1	106.23 (17)	C22—C21—C26	121.5 (3)
C27—N6—Ni1	109.56 (16)	C23—C22—C21	117.1 (3)
C19—N6—Ni1	104.44 (16)	C23—C22—H22	121.5
C20—N7—C26	105.3 (2)	C21—C22—H22	121.5
C20—N7—Ni1	108.97 (17)	C22—C23—C24	121.9 (3)
C26—N7—Ni1	144.66 (18)	C22—C23—H23	119.1
C20—N8—C21	107.5 (2)	C24—C23—H23	119.1
C20—N8—H8	126.3	C25—C24—C23	121.4 (3)
C21—N8—H8	126.3	C25—C24—H24	119.3
C28—N9—C34	105.2 (2)	C23—C24—H24	119.3
C28—N9—Ni1	112.28 (18)	C24—C25—C26	117.7 (3)
C34—N9—Ni1	142.14 (18)	C24—C25—H25	121.1
C28—N10—C29	107.9 (2)	C26—C25—H25	121.1
C28—N10—H10	126.1	C25—C26—N7	130.9 (3)
C29—N10—H10	126.1	C25—C26—C21	120.4 (3)
N3—C1—C2	107.0 (2)	N7—C26—C21	108.7 (2)
N3—C1—H1A	110.3	C28—C27—N6	110.4 (2)
C2—C1—H1A	110.3	C28—C27—H27A	109.6
N3—C1—H1B	110.3	N6—C27—H27A	109.6
C2—C1—H1B	110.3	C28—C27—H27B	109.6
H1A—C1—H1B	108.6	N6—C27—H27B	109.6
N1—C2—N2	112.9 (2)	H27A—C27—H27B	108.1
N1—C2—C1	121.2 (2)	N9—C28—N10	112.8 (2)
N2—C2—C1	126.0 (2)	N9—C28—C27	121.6 (2)
N2—C3—C4	133.2 (3)	N10—C28—C27	125.6 (2)
N2—C3—C8	105.2 (2)	N10—C29—C30	132.7 (3)
C4—C3—C8	121.6 (3)	N10—C29—C34	105.2 (2)
C5—C4—C3	116.8 (3)	C30—C29—C34	122.1 (3)
C5—C4—H4	121.6	C31—C30—C29	116.6 (3)
C3—C4—H4	121.6	C31—C30—H30	121.7
C4—C5—C6	121.8 (3)	C29—C30—H30	121.7
C4—C5—H5	119.1	C30—C31—C32	121.9 (3)
C6—C5—H5	119.1	C30—C31—H31	119.0
C7—C6—C5	121.7 (3)	C32—C31—H31	119.0
C7—C6—H6	119.1	C33—C32—C31	122.0 (3)
C5—C6—H6	119.1	C33—C32—H32	119.0
C6—C7—C8	117.2 (3)	C31—C32—H32	119.0
C6—C7—H7	121.4	C32—C33—C34	117.2 (3)
C8—C7—H7	121.4	C32—C33—H33	121.4
C7—C8—N1	130.5 (2)	C34—C33—H33	121.4
C7—C8—C3	120.8 (3)	N9—C34—C33	130.9 (3)
N1—C8—C3	108.7 (2)	N9—C34—C29	108.9 (2)
C10—C9—N3	110.8 (2)	C33—C34—C29	120.2 (3)
C10—C9—H9A	109.5	O2—N11—O1	120.4 (4)
N3—C9—H9A	109.5	O2—N11—O3	122.0 (4)
C10—C9—H9B	109.5	O1—N11—O3	117.6 (3)
N3—C9—H9B	109.5	O5—N12—O6	118.9 (3)
H9A—C9—H9B	108.1	O5—N12—O4	121.4 (3)
N4—C10—N5	112.8 (2)	O6—N12—O4	119.7 (3)
N4—C10—C9	123.3 (3)	C35—O7—H7A	109.5
N5—C10—C9	123.9 (3)	O7—C35—H35A	109.5
N5—C11—C12	132.3 (3)	O7—C35—H35B	109.5
N5—C11—C16	105.6 (3)	H35A—C35—H35B	109.5
C12—C11—C16	122.1 (3)	O7—C35—H35C	109.5
C13—C12—C11	116.5 (3)	H35A—C35—H35C	109.5
C13—C12—H12	121.7	H35B—C35—H35C	109.5
N4—Ni1—N1—C2	−103.3 (2)	C4—C3—C8—N1	179.2 (3)
N7—Ni1—N1—C2	164.51 (18)	C1—N3—C9—C10	−116.4 (2)
N9—Ni1—N1—C2	68.1 (2)	C17—N3—C9—C10	113.8 (3)
N6—Ni1—N1—C2	−2.6 (4)	Ni1—N3—C9—C10	−1.7 (3)
N3—Ni1—N1—C2	−22.67 (19)	C16—N4—C10—N5	−1.4 (3)
N4—Ni1—N1—C8	82.9 (3)	Ni1—N4—C10—N5	−162.37 (19)
N7—Ni1—N1—C8	−9.3 (3)	C16—N4—C10—C9	175.5 (3)
N9—Ni1—N1—C8	−105.7 (3)	Ni1—N4—C10—C9	14.5 (3)
N6—Ni1—N1—C8	−176.4 (3)	C11—N5—C10—N4	1.7 (3)
N3—Ni1—N1—C8	163.5 (3)	C11—N5—C10—C9	−175.2 (3)
N1—Ni1—N3—C1	35.43 (17)	N3—C9—C10—N4	−8.5 (4)
N4—Ni1—N3—C1	125.29 (18)	N3—C9—C10—N5	168.0 (3)
N7—Ni1—N3—C1	−163.6 (2)	C10—N5—C11—C12	176.4 (3)
N9—Ni1—N3—C1	−57.43 (17)	C10—N5—C11—C16	−1.2 (3)
N6—Ni1—N3—C1	−138.30 (18)	N5—C11—C12—C13	−177.2 (3)
N1—Ni1—N3—C17	156.64 (18)	C16—C11—C12—C13	0.0 (5)
N4—Ni1—N3—C17	−113.50 (18)	C11—C12—C13—C14	0.1 (5)
N7—Ni1—N3—C17	−42.4 (3)	C12—C13—C14—C15	0.0 (6)
N9—Ni1—N3—C17	63.77 (17)	C13—C14—C15—C16	−0.2 (5)
N6—Ni1—N3—C17	−17.10 (17)	C14—C15—C16—N4	176.9 (3)
N1—Ni1—N3—C9	−83.22 (19)	C14—C15—C16—C11	0.3 (4)
N4—Ni1—N3—C9	6.64 (18)	C10—N4—C16—C15	−176.2 (3)
N7—Ni1—N3—C9	77.7 (3)	Ni1—N4—C16—C15	−22.7 (5)
N9—Ni1—N3—C9	−176.08 (18)	C10—N4—C16—C11	0.6 (3)
N6—Ni1—N3—C9	103.04 (19)	Ni1—N4—C16—C11	154.2 (2)
N1—Ni1—N4—C10	68.3 (2)	N5—C11—C16—C15	177.6 (2)
N7—Ni1—N4—C10	−172.63 (19)	C12—C11—C16—C15	−0.2 (5)
N6—Ni1—N4—C10	−93.6 (2)	N5—C11—C16—N4	0.3 (3)
N3—Ni1—N4—C10	−11.05 (19)	C12—C11—C16—N4	−177.5 (3)
N1—Ni1—N4—C16	−83.9 (3)	C1—N3—C17—C18	157.2 (2)
N7—Ni1—N4—C16	35.2 (3)	C9—N3—C17—C18	−75.6 (3)
N6—Ni1—N4—C16	114.2 (3)	Ni1—N3—C17—C18	44.1 (3)
N3—Ni1—N4—C16	−163.2 (3)	C27—N6—C18—C17	−79.0 (3)
N1—Ni1—N6—C18	−32.7 (4)	C19—N6—C18—C17	155.4 (2)
N4—Ni1—N6—C18	66.99 (18)	Ni1—N6—C18—C17	41.0 (3)
N7—Ni1—N6—C18	158.83 (18)	N3—C17—C18—N6	−60.0 (3)
N9—Ni1—N6—C18	−105.20 (18)	C18—N6—C19—C20	−157.6 (2)
N3—Ni1—N6—C18	−12.80 (17)	C27—N6—C19—C20	75.2 (3)
N1—Ni1—N6—C27	89.3 (3)	Ni1—N6—C19—C20	−42.1 (3)
N4—Ni1—N6—C27	−171.09 (17)	C26—N7—C20—N8	0.6 (3)
N7—Ni1—N6—C27	−79.25 (18)	Ni1—N7—C20—N8	−170.71 (19)
N9—Ni1—N6—C27	16.73 (17)	C26—N7—C20—C19	−179.8 (3)
N3—Ni1—N6—C27	109.12 (18)	Ni1—N7—C20—C19	8.9 (3)
N1—Ni1—N6—C19	−153.5 (3)	C21—N8—C20—N7	0.4 (4)
N4—Ni1—N6—C19	−53.87 (19)	C21—N8—C20—C19	−179.2 (3)
N7—Ni1—N6—C19	37.98 (18)	N6—C19—C20—N7	23.8 (4)
N9—Ni1—N6—C19	133.95 (19)	N6—C19—C20—N8	−156.6 (3)
N3—Ni1—N6—C19	−133.65 (19)	C20—N8—C21—C22	178.1 (3)
N1—Ni1—N7—C20	157.87 (18)	C20—N8—C21—C26	−1.2 (3)
N4—Ni1—N7—C20	68.5 (2)	N8—C21—C22—C23	179.3 (3)
N9—Ni1—N7—C20	−106.3 (2)	C26—C21—C22—C23	−1.4 (5)
N6—Ni1—N7—C20	−26.26 (19)	C21—C22—C23—C24	−0.2 (6)
N3—Ni1—N7—C20	−0.6 (4)	C22—C23—C24—C25	0.8 (6)
N1—Ni1—N7—C26	−7.5 (4)	C23—C24—C25—C26	0.4 (5)
N4—Ni1—N7—C26	−96.9 (3)	C24—C25—C26—N7	178.6 (3)
N9—Ni1—N7—C26	88.3 (3)	C24—C25—C26—C21	−2.0 (4)
N6—Ni1—N7—C26	168.4 (3)	C20—N7—C26—C25	178.1 (3)
N3—Ni1—N7—C26	−165.9 (3)	Ni1—N7—C26—C25	−16.2 (5)
N1—Ni1—N9—C28	−168.38 (18)	C20—N7—C26—C21	−1.3 (3)
N7—Ni1—N9—C28	72.12 (18)	Ni1—N7—C26—C21	164.3 (2)
N6—Ni1—N9—C28	−5.90 (17)	N8—C21—C26—C25	−178.0 (3)
N3—Ni1—N9—C28	−89.15 (18)	C22—C21—C26—C25	2.6 (5)
N1—Ni1—N9—C34	3.2 (3)	N8—C21—C26—N7	1.6 (3)
N7—Ni1—N9—C34	−116.3 (3)	C22—C21—C26—N7	−177.8 (3)
N6—Ni1—N9—C34	165.7 (3)	C18—N6—C27—C28	94.1 (3)
N3—Ni1—N9—C34	82.5 (3)	C19—N6—C27—C28	−137.9 (2)
C17—N3—C1—C2	−153.8 (2)	Ni1—N6—C27—C28	−23.9 (3)
C9—N3—C1—C2	78.5 (3)	C34—N9—C28—N10	−0.3 (3)
Ni1—N3—C1—C2	−40.5 (2)	Ni1—N9—C28—N10	174.35 (17)
C8—N1—C2—N2	1.1 (3)	C34—N9—C28—C27	178.3 (2)
Ni1—N1—C2—N2	−175.06 (18)	Ni1—N9—C28—C27	−7.0 (3)
C8—N1—C2—C1	−179.1 (2)	C29—N10—C28—N9	−0.1 (3)
Ni1—N1—C2—C1	4.8 (3)	C29—N10—C28—C27	−178.7 (2)
C3—N2—C2—N1	−0.6 (3)	N6—C27—C28—N9	21.6 (3)
C3—N2—C2—C1	179.6 (3)	N6—C27—C28—N10	−160.0 (2)
N3—C1—C2—N1	26.7 (4)	C28—N10—C29—C30	179.3 (3)
N3—C1—C2—N2	−153.5 (3)	C28—N10—C29—C34	0.5 (3)
C2—N2—C3—C4	−178.3 (3)	N10—C29—C30—C31	−178.2 (3)
C2—N2—C3—C8	−0.2 (3)	C34—C29—C30—C31	0.4 (4)
N2—C3—C4—C5	177.8 (3)	C29—C30—C31—C32	−0.7 (5)
C8—C3—C4—C5	−0.1 (5)	C30—C31—C32—C33	0.7 (5)
C3—C4—C5—C6	−1.1 (5)	C31—C32—C33—C34	−0.3 (4)
C4—C5—C6—C7	0.6 (5)	C28—N9—C34—C33	−178.9 (3)
C5—C6—C7—C8	1.1 (5)	Ni1—N9—C34—C33	9.1 (5)
C6—C7—C8—N1	−179.0 (3)	C28—N9—C34—C29	0.7 (3)
C6—C7—C8—C3	−2.2 (4)	Ni1—N9—C34—C29	−171.3 (2)
C2—N1—C8—C7	175.9 (3)	C32—C33—C34—N9	179.6 (3)
Ni1—N1—C8—C7	−10.1 (5)	C32—C33—C34—C29	0.0 (4)
C2—N1—C8—C3	−1.1 (3)	N10—C29—C34—N9	−0.7 (3)
Ni1—N1—C8—C3	172.9 (2)	C30—C29—C34—N9	−179.7 (3)
N2—C3—C8—C7	−176.6 (3)	N10—C29—C34—C33	178.9 (2)
C4—C3—C8—C7	1.8 (4)	C30—C29—C34—C33	−0.1 (4)
N2—C3—C8—N1	0.8 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O6^i	0.86	2.03	2.813 (3)	151
N2—H2···O5^i	0.86	2.33	3.035 (3)	140
N2—H2···N12^i	0.86	2.53	3.348 (4)	159
N5—H5A···O3	0.86	2.05	2.879 (4)	161
N5—H5A···O1	0.86	2.48	3.182 (4)	139
N8—H8···O7^ii	0.86	1.92	2.763 (3)	168
N10—H10···O3^iii	0.86	2.35	3.040 (4)	137
N10—H10···O4^iii	0.86	2.37	3.063 (3)	139
O7—H7A···O2^iv	0.82	2.24	3.032 (5)	164
O7—H7A···O1^iv	0.82	2.42	3.086 (4)	139

Symmetry codes: (i) x, y+1, z; (ii) x+1, y, z; (iii) x+1, y+1, z; (iv) −x, −y+1, −z+1.