Bis­(di-2-pyridyl­methanediol-κ³N,O,N′)­nickel(II) dilactate

Di-2-pyridyl ketone reacts with nickel(II) dilactate in water to form the title compound, [Ni(C₁₁H₁₀N₂O₂)₂](C₃H₅O₃)₂, whose Ni atom is N,O,N′-chelated by the ketals in an octahedral environment. The cation interacts with the two anions through extensive hydrogen bonds to furnish a helical chain motif that runs along the b axis.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.004 Å
• Disorder in solvent or counterion
• R factor = 0.045
• wR factor = 0.112
• Data-to-parameter ratio = 14.6

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low .......       0.97
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT199_ALERT_1_C Check the Reported cell_measurement_temperature         293
PLAT200_ALERT_1_C Check the Reported cell_ambient_temperature ....        293
PLAT244_ALERT_4_C Low   'Solvent' Ueq as Compared to Neighbors for       C24'
PLAT244_ALERT_4_C Low   'Solvent' Ueq as Compared to Neighbors for        C27
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....       2.26
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....       2.19
PLAT302_ALERT_4_C Anion/Solvent Disorder .........................      33.00 Perc.

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

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

---

Computing details

Data collection: CrystalClear (Rigaku/MSC, 2002); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97.

Bis(di-2-pyridylmethanediol-κ³N,O,N')nickel(II) dilactate

Crystal data

[Ni(C11H10N2O2)2](C3H5O3)2	F(000) = 1336
Mr = 641.27	Dx = 1.513 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 12650 reflections
a = 10.8401 (7) Å	θ = 1.8–27.5°
b = 17.359 (1) Å	µ = 0.76 mm^−1
c = 15.611 (1) Å	T = 293 K
β = 106.534 (1)°	Block, green
V = 2816.1 (3) Å^3	0.36 × 0.32 × 0.26 mm
Z = 4

Data collection

Rigaku Mercury CCD area-detector diffractometer	6277 independent reflections
Radiation source: rotating anode	5018 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.029
ω scans	θmax = 27.5°, θmin = 1.8°
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2002)	h = −14→13
Tmin = 0.764, Tmax = 0.823	k = −19→22
16648 measured reflections	l = −13→19

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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.112	H-atom parameters constrained
S = 1.01	w = 1/[σ^2(Fo^2) + (0.0567P)^2 + 0.828P] where P = (Fo^2 + 2Fc^2)/3
6277 reflections	(Δ/σ)max = 0.001
430 parameters	Δρmax = 0.40 e Å^−3
14 restraints	Δρmin = −0.23 e Å^−3

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
Ni1	0.88579 (2)	0.32132 (2)	0.63906 (2)	0.0280 (1)
O1	0.7054 (1)	0.3742 (1)	0.6082 (1)	0.0355 (4)
O2	0.5363 (2)	0.3681 (1)	0.6746 (1)	0.0446 (4)
O3	1.0672 (3)	0.2690 (1)	0.6742 (1)	0.0312 (3)
O4	1.2382 (1)	0.2706 (1)	0.6103 (1)	0.0397 (4)
O5	0.5456 (2)	0.5184 (1)	0.6883 (1)	0.0533 (5)
O6	0.6797 (2)	0.5170 (1)	0.6045 (2)	0.0829 (8)
O7	0.4875 (2)	0.6653 (1)	0.6592 (2)	0.0660 (8)	0.652 (5)
O7'	0.4875 (2)	0.6653 (1)	0.6592 (2)	0.0660 (8)	0.35
O8	0.4126 (2)	0.6219 (1)	0.8236 (1)	0.0515 (5)
O9	0.2544 (2)	0.6206 (1)	0.8881 (2)	0.0574 (5)
O10	0.4503 (3)	0.4718 (1)	0.8410 (2)	0.0809 (9)	0.789 (5)
O10'	0.4503 (3)	0.4718 (1)	0.8410 (2)	0.0809 (9)	0.21
N1	0.7649 (2)	0.2301 (1)	0.6501 (1)	0.0329 (4)
N2	0.8796 (2)	0.3542 (1)	0.7636 (1)	0.0337 (4)
N3	0.8950 (2)	0.2857 (1)	0.5158 (1)	0.0312 (4)
N4	1.0076 (2)	0.4111 (1)	0.6256 (1)	0.0320 (4)
C1	0.7771 (2)	0.1543 (2)	0.6422 (2)	0.0407 (6)
C2	0.6829 (3)	0.1032 (2)	0.6488 (2)	0.0477 (6)
C3	0.5705 (2)	0.1311 (2)	0.6620 (2)	0.0471 (7)
C4	0.5566 (2)	0.2096 (2)	0.6700 (2)	0.0406 (6)
C5	0.6568 (2)	0.2572 (1)	0.6654 (2)	0.0332 (5)
C6	0.6581 (2)	0.3437 (1)	0.6784 (2)	0.0340 (5)
C7	0.7579 (2)	0.3629 (1)	0.7671 (2)	0.0329 (5)
C8	0.7298 (3)	0.3836 (1)	0.8448 (2)	0.0411 (6)
C9	0.8301 (3)	0.3951 (2)	0.9209 (2)	0.0491 (7)
C10	0.9546 (3)	0.3865 (2)	0.9170 (2)	0.0515 (7)
C11	0.9757 (2)	0.3662 (2)	0.8374 (2)	0.0429 (6)
C12	0.7996 (2)	0.2721 (1)	0.4412 (2)	0.0375 (5)
C13	0.8230 (3)	0.2445 (2)	0.3649 (2)	0.0465 (6)
C14	0.9473 (3)	0.2288 (2)	0.3653 (2)	0.0483 (7)
C15	1.0464 (2)	0.2444 (2)	0.4411 (2)	0.0401 (6)
C16	1.0176 (2)	0.2731 (1)	0.5151 (2)	0.0301 (5)
C17	1.1161 (2)	0.2963 (1)	0.6029 (2)	0.0302 (5)
C18	1.1149 (2)	0.3834 (1)	0.6105 (1)	0.0317 (5)
C19	1.2133 (2)	0.4302 (2)	0.6005 (2)	0.0427 (6)
C20	1.1985 (3)	0.5091 (2)	0.6065 (2)	0.0515 (7)
C21	1.0883 (3)	0.5377 (2)	0.6215 (2)	0.0513 (7)
C22	0.9946 (2)	0.4874 (2)	0.6311 (2)	0.0412 (6)
C23	0.5999 (3)	0.5494 (2)	0.6378 (2)	0.0530 (7)
C24	0.5501 (5)	0.6273 (2)	0.5988 (4)	0.046 (1)	0.652 (5)
C25	0.6605 (6)	0.6769 (3)	0.5946 (5)	0.064 (2)	0.652 (5)
C24'	0.6024 (8)	0.6402 (4)	0.6400 (5)	0.035 (2)	0.348 (5)
C25'	0.584 (1)	0.6670 (6)	0.5457 (5)	0.053 (2)	0.348 (5)
C26	0.3359 (2)	0.5882 (2)	0.8579 (2)	0.0427 (6)
C27	0.3334 (5)	0.4997 (2)	0.8541 (3)	0.047 (1)	0.789 (5)
C28	0.3194 (5)	0.4637 (2)	0.9385 (3)	0.065 (1)	0.789 (5)
C27'	0.375 (1)	0.5089 (6)	0.893 (1)	0.037 (4)	0.211 (5)
C28'	0.252 (1)	0.4633 (8)	0.869 (1)	0.062 (5)	0.211 (5)
H1o	0.7117	0.4230	0.6108	0.043*
H2o	0.5365	0.4167	0.6816	0.067*
H3o	1.0615	0.2201	0.6741	0.037*
H4o	1.2381	0.2217	0.6072	0.060*
H7o	0.4669	0.6317	0.6924	0.079*
H10o	0.4740	0.5015	0.8054	0.097*
H1	0.8516	0.1352	0.6318	0.049*
H2	0.6950	0.0505	0.6445	0.057*
H3	0.5052	0.0976	0.6655	0.057*
H4	0.4815	0.2300	0.6782	0.049*
H8	0.6450	0.3896	0.8458	0.049*
H9	0.8139	0.4086	0.9743	0.059*
H10	1.0235	0.3944	0.9676	0.062*
H11	1.0599	0.3607	0.8348	0.051*
H12	0.7151	0.2817	0.4410	0.045*
H13	0.7554	0.2365	0.3136	0.056*
H14	0.9645	0.2078	0.3151	0.058*
H15	1.1314	0.2357	0.4420	0.048*
H19	1.2868	0.4094	0.5901	0.051*
H20	1.2626	0.5424	0.6004	0.062*
H21	1.0770	0.5906	0.6252	0.062*
H22	0.9205	0.5070	0.6417	0.049*
H24	0.4894	0.6212	0.5392	0.055*	0.652 (5)
H25a	0.6289	0.7261	0.5696	0.095*	0.652 (5)
H25b	0.7066	0.6526	0.5578	0.095*	0.652 (5)
H25c	0.7171	0.6840	0.6538	0.095*	0.652 (5)
H24'	0.6807	0.6609	0.6818	0.042*	0.348 (5)
H25d	0.5852	0.7222	0.5443	0.079*	0.348 (5)
H25e	0.5022	0.6488	0.5087	0.079*	0.348 (5)
H25f	0.6515	0.6469	0.5238	0.079*	0.348 (5)
H27	0.2613	0.4832	0.8038	0.056*	0.789 (5)
H28a	0.3153	0.4087	0.9320	0.098*	0.789 (5)
H28b	0.2418	0.4820	0.9497	0.098*	0.789 (5)
H28c	0.3920	0.4774	0.9877	0.098*	0.789 (5)
H27'	0.4188	0.5085	0.9575	0.045*	0.211 (5)
H28d	0.2711	0.4093	0.8754	0.093*	0.211 (5)
H28e	0.2042	0.4741	0.8083	0.093*	0.211 (5)
H28f	0.2010	0.4775	0.9080	0.093*	0.211 (5)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Ni1	0.0234 (2)	0.0337 (2)	0.0297 (2)	0.0007 (1)	0.0120 (1)	−0.0014 (1)
O1	0.031 (1)	0.038 (1)	0.040 (1)	0.004 (1)	0.015 (1)	0.002 (1)
O2	0.028 (1)	0.045 (1)	0.067 (1)	0.004 (1)	0.024 (1)	−0.004 (1)
O3	0.028 (1)	0.036 (1)	0.031 (1)	0.001 (1)	0.011 (1)	0.004 (1)
O4	0.023 (1)	0.043 (1)	0.056 (1)	0.002 (1)	0.016 (1)	0.000 (1)
O5	0.061 (1)	0.044 (1)	0.069 (1)	0.004 (1)	0.040 (1)	0.004 (1)
O6	0.093 (2)	0.053 (1)	0.139 (2)	0.031 (1)	0.091 (2)	0.035 (1)
O7	0.070 (2)	0.055 (1)	0.091 (2)	0.026 (1)	0.049 (1)	0.020 (1)
O7'	0.070 (2)	0.055 (1)	0.091 (2)	0.026 (1)	0.049 (1)	0.020 (1)
O8	0.052 (1)	0.044 (1)	0.073 (1)	−0.006 (1)	0.042 (1)	−0.008 (1)
O9	0.054 (1)	0.046 (1)	0.091 (2)	0.002 (1)	0.050 (1)	−0.001 (1)
O10	0.104 (2)	0.059 (2)	0.110 (2)	0.033 (1)	0.080 (2)	0.022 (1)
O10'	0.104 (2)	0.059 (2)	0.110 (2)	0.033 (1)	0.080 (2)	0.022 (1)
N1	0.029 (1)	0.036 (1)	0.037 (1)	0.001 (1)	0.014 (1)	−0.003 (1)
N2	0.032 (1)	0.039 (1)	0.033 (1)	−0.001 (1)	0.015 (1)	−0.002 (1)
N3	0.027 (1)	0.034 (1)	0.032 (1)	−0.001 (1)	0.009 (1)	0.000 (1)
N4	0.030 (1)	0.035 (1)	0.033 (1)	−0.001 (1)	0.012 (1)	−0.001 (1)
C1	0.034 (1)	0.040 (1)	0.049 (2)	0.005 (1)	0.013 (1)	−0.007 (1)
C2	0.049 (2)	0.034 (1)	0.059 (2)	−0.005 (1)	0.013 (1)	−0.008 (1)
C3	0.039 (1)	0.049 (2)	0.054 (2)	−0.015 (1)	0.016 (1)	−0.005 (1)
C4	0.031 (1)	0.047 (2)	0.048 (2)	−0.007 (1)	0.018 (1)	−0.009 (1)
C5	0.027 (1)	0.041 (1)	0.034 (1)	−0.001 (1)	0.011 (1)	−0.004 (1)
C6	0.026 (1)	0.037 (1)	0.044 (1)	0.002 (1)	0.019 (1)	−0.001 (1)
C7	0.036 (1)	0.028 (1)	0.040 (1)	−0.002 (1)	0.021 (1)	0.000 (1)
C8	0.049 (2)	0.036 (1)	0.049 (2)	0.000 (1)	0.031 (1)	0.000 (1)
C9	0.073 (2)	0.045 (2)	0.038 (2)	−0.005 (1)	0.031 (1)	−0.005 (1)
C10	0.060 (2)	0.061 (2)	0.032 (1)	−0.007 (1)	0.010 (1)	−0.007 (1)
C11	0.036 (1)	0.053 (2)	0.040 (1)	−0.004 (1)	0.011 (1)	−0.002 (1)
C12	0.032 (1)	0.041 (1)	0.037 (1)	−0.002 (1)	0.006 (1)	0.001 (1)
C13	0.053 (2)	0.049 (2)	0.032 (1)	−0.009 (1)	0.002 (1)	−0.001 (1)
C14	0.067 (2)	0.052 (2)	0.031 (1)	−0.004 (1)	0.022 (1)	−0.008 (1)
C15	0.042 (1)	0.044 (2)	0.041 (1)	0.002 (1)	0.022 (1)	−0.002 (1)
C16	0.030 (1)	0.029 (1)	0.034 (1)	−0.001 (1)	0.014 (1)	0.001 (1)
C17	0.024 (1)	0.036 (1)	0.035 (1)	−0.001 (1)	0.015 (1)	0.003 (1)
C18	0.029 (1)	0.039 (1)	0.028 (1)	−0.003 (1)	0.009 (1)	−0.002 (1)
C19	0.033 (1)	0.048 (2)	0.050 (2)	−0.006 (1)	0.016 (1)	−0.003 (1)
C20	0.045 (2)	0.048 (2)	0.063 (2)	−0.016 (1)	0.019 (1)	0.001 (1)
C21	0.059 (2)	0.034 (2)	0.063 (2)	−0.006 (1)	0.020 (1)	0.001 (1)
C22	0.040 (1)	0.039 (1)	0.047 (2)	0.002 (1)	0.017 (1)	−0.002 (1)
C23	0.051 (2)	0.044 (2)	0.075 (2)	0.012 (1)	0.035 (2)	0.013 (1)
C24	0.047 (3)	0.045 (3)	0.042 (3)	0.009 (2)	0.005 (2)	0.006 (2)
C25	0.084 (4)	0.039 (3)	0.082 (4)	−0.007 (3)	0.047 (4)	0.001 (3)
C24'	0.027 (4)	0.044 (5)	0.032 (4)	0.009 (3)	0.004 (3)	0.003 (3)
C25'	0.058 (6)	0.055 (6)	0.043 (5)	0.009 (4)	0.012 (4)	0.000 (4)
C26	0.038 (1)	0.044 (2)	0.051 (2)	0.000 (1)	0.020 (1)	−0.001 (1)
C27	0.052 (3)	0.042 (2)	0.049 (3)	0.001 (2)	0.021 (2)	−0.005 (2)
C28	0.085 (3)	0.049 (2)	0.077 (3)	−0.003 (2)	0.045 (3)	0.000 (2)
C27'	0.03 (1)	0.046 (8)	0.033 (8)	0.003 (6)	0.006 (6)	0.006 (6)
C28'	0.06 (1)	0.029 (7)	0.095 (14)	−0.021 (7)	0.024 (9)	0.005 (7)

Geometric parameters (Å, º)

Ni1—O1	2.088 (2)	C23—C24'	1.575 (7)
Ni1—O3	2.093 (2)	C24—C25	1.491 (6)
Ni1—N1	2.093 (2)	C24'—C25'	1.502 (8)
Ni1—N2	2.046 (2)	C26—C27'	1.500 (9)
Ni1—N3	2.050 (2)	C26—C27	1.537 (4)
Ni1—N4	2.092 (2)	C27—C28	1.505 (5)
O1—C6	1.437 (3)	C27'—C28'	1.509 (9)
O2—C6	1.373 (3)	O1—H1o	0.85
O3—C17	1.442 (3)	O2—H2o	0.85
O4—C17	1.370 (3)	O3—H3o	0.85
O5—C23	1.234 (3)	O4—H4o	0.85
O6—C23	1.262 (3)	O7—H7o	0.85
O7—C24	1.466 (5)	O10—H10o	0.85
O8—C26	1.255 (3)	C1—H1	0.93
O9—C26	1.247 (3)	C2—H2	0.93
O10—C27	1.426 (5)	C3—H3	0.93
N1—C1	1.332 (3)	C4—H4	0.93
N1—C5	1.345 (3)	C8—H8	0.93
N2—C11	1.331 (3)	C9—H9	0.93
N2—C7	1.344 (3)	C10—H10	0.93
N3—C12	1.341 (3)	C11—H11	0.93
N3—C16	1.350 (3)	C12—H12	0.93
N4—C22	1.336 (3)	C13—H13	0.93
N4—C18	1.340 (3)	C14—H14	0.93
C1—C2	1.378 (4)	C15—H15	0.93
C2—C3	1.380 (4)	C19—H19	0.93
C3—C4	1.379 (4)	C20—H20	0.93
C4—C5	1.383 (3)	C21—H21	0.93
C5—C6	1.514 (3)	C22—H22	0.93
C6—C7	1.532 (3)	C24—H24	0.98
C7—C8	1.380 (3)	C25—H25a	0.96
C8—C9	1.378 (4)	C25—H25b	0.96
C9—C10	1.376 (4)	C25—H25c	0.96
C10—C11	1.373 (3)	C24'—H24'	0.98
C12—C13	1.371 (3)	C25'—H25d	0.96
C13—C14	1.373 (4)	C25'—H25e	0.96
C14—C15	1.380 (4)	C25'—H25f	0.96
C15—C16	1.374 (3)	C27—H27	0.98
C16—C17	1.531 (3)	C28—H28a	0.96
C17—C18	1.519 (3)	C28—H28b	0.96
C18—C19	1.384 (3)	C28—H28c	0.96
C19—C20	1.385 (4)	C27'—H27'	0.98
C20—C21	1.374 (4)	C28'—H28d	0.96
C21—C22	1.380 (4)	C28'—H28e	0.96
C23—C24	1.518 (5)	C28'—H28f	0.96
O1—Ni1—O3	178.26 (6)	O8—C26—C27'	115.5 (6)
O1—Ni1—N1	77.54 (7)	O9—C26—C27	117.3 (3)
O1—Ni1—N2	79.35 (7)	O8—C26—C27	117.1 (3)
O1—Ni1—N3	102.01 (7)	O10—C27—C28	107.5 (4)
O1—Ni1—N4	103.04 (7)	O10—C27—C26	109.8 (3)
O3—Ni1—N1	102.34 (7)	C28—C27—C26	112.8 (3)
O3—Ni1—N2	98.92 (7)	C26—C27'—C28'	104.5 (9)
O3—Ni1—N3	79.73 (6)	C6—O1—H1o	111.7
O3—Ni1—N4	77.12 (7)	Ni1—O1—H1o	111.7
N1—Ni1—N2	86.69 (7)	C6—O2—H2o	109.5
N1—Ni1—N3	92.74 (7)	C17—O3—H3o	111.7
N1—Ni1—N4	178.67 (7)	Ni1—O3—H3o	111.7
N2—Ni1—N3	178.39 (8)	C17—O4—H4o	109.5
N2—Ni1—N4	94.59 (8)	N1—C1—H1	118.9
N3—Ni1—N4	85.97 (7)	C2—C1—H1	118.9
C6—O1—Ni1	100.1 (1)	C1—C2—H2	120.3
C17—O3—Ni1	100.3 (1)	C3—C2—H2	120.3
C1—N1—C5	118.4 (2)	C4—C3—H3	120.5
C1—N1—Ni1	131.2 (2)	C2—C3—H3	120.5
C5—N1—Ni1	110.4 (2)	C3—C4—H4	120.7
C11—N2—C7	118.9 (2)	C5—C4—H4	120.7
C11—N2—Ni1	129.6 (2)	C9—C8—H8	120.7
C7—N2—Ni1	111.6 (2)	C7—C8—H8	120.7
C12—N3—C16	118.8 (2)	C10—C9—H9	120.4
C12—N3—Ni1	129.6 (2)	C8—C9—H9	120.4
C16—N3—Ni1	111.5 (1)	C11—C10—H10	120.5
C22—N4—C18	118.6 (2)	C9—C10—H10	120.5
C22—N4—Ni1	130.6 (2)	N2—C11—H11	118.9
C18—N4—Ni1	110.8 (2)	C10—C11—H11	118.9
N1—C1—C2	122.2 (2)	N3—C12—H12	119.0
C1—C2—C3	119.4 (2)	C13—C12—H12	119.0
C4—C3—C2	118.9 (2)	C12—C13—H13	120.4
C3—C4—C5	118.5 (2)	C14—C13—H13	120.4
N1—C5—C4	122.5 (2)	C13—C14—H14	120.4
N1—C5—C6	113.2 (2)	C15—C14—H14	120.4
C4—C5—C6	124.3 (2)	C16—C15—H15	120.5
O2—C6—O1	113.7 (2)	C14—C15—H15	120.5
O2—C6—C5	109.2 (2)	C18—C19—H19	121.2
O1—C6—C5	104.8 (2)	C20—C19—H19	121.2
O2—C6—C7	113.3 (2)	C21—C20—H20	120.2
O1—C6—C7	107.2 (2)	C19—C20—H20	120.2
C5—C6—C7	108.3 (2)	C20—C21—H21	120.3
N2—C7—C8	122.0 (2)	C22—C21—H21	120.3
N2—C7—C6	112.8 (2)	N4—C22—H22	119.1
C8—C7—C6	125.2 (2)	C21—C22—H22	119.1
C9—C8—C7	118.6 (2)	O7—C24—H24	110.6
C10—C9—C8	119.3 (2)	C25—C24—H24	110.6
C11—C10—C9	119.1 (2)	C23—C24—H24	110.6
N2—C11—C10	122.2 (2)	C24—C25—H25a	109.5
N3—C12—C13	121.9 (2)	C24—C25—H25b	109.5
C12—C13—C14	119.3 (2)	H25a—C25—H25b	109.5
C13—C14—C15	119.2 (2)	C24—C25—H25c	109.5
C16—C15—C14	119.0 (2)	H25a—C25—H25c	109.5
N3—C16—C15	121.7 (2)	H25b—C25—H25c	109.5
N3—C16—C17	112.8 (2)	C25'—C24'—H24'	112.9
C15—C16—C17	125.4 (2)	C23—C24'—H24'	112.9
O4—C17—O3	112.7 (2)	C24'—C25'—H25d	109.5
O4—C17—C18	110.2 (2)	C24'—C25'—H25e	109.5
O3—C17—C18	104.7 (2)	H25d—C25'—H25e	109.5
O4—C17—C16	113.7 (2)	C24'—C25'—H25f	109.5
O3—C17—C16	106.8 (2)	H25d—C25'—H25f	109.5
C18—C17—C16	108.2 (2)	H25e—C25'—H25f	109.5
N4—C18—C19	123.0 (2)	O10—C27—H27	108.9
N4—C18—C17	113.4 (2)	C28—C27—H27	108.9
C19—C18—C17	123.5 (2)	C26—C27—H27	108.9
C18—C19—C20	117.6 (2)	C27—C28—H28a	109.5
C21—C20—C19	119.5 (2)	C27—C28—H28b	109.5
C20—C21—C22	119.4 (3)	H28a—C28—H28b	109.5
N4—C22—C21	121.7 (2)	C27—C28—H28c	109.5
O5—C23—O6	125.2 (3)	H28a—C28—H28c	109.5
O5—C23—C24	117.7 (3)	H28b—C28—H28c	109.5
O6—C23—C24	116.1 (3)	C26—C27'—H27'	112.8
O5—C23—C24'	115.5 (3)	C28'—C27'—H27'	112.8
O6—C23—C24'	116.5 (3)	C27'—C28'—H28d	109.5
O7—C24—C25	107.0 (4)	C27'—C28'—H28e	109.5
O7—C24—C23	108.6 (3)	H28d—C28'—H28e	109.5
C25—C24—C23	109.5 (4)	C27'—C28'—H28f	109.5
C25'—C24'—C23	106.9 (6)	H28d—C28'—H28f	109.5
O9—C26—O8	125.3 (2)	H28e—C28'—H28f	109.5
O9—C26—C27'	115.7 (7)
N2—Ni1—O1—C6	−43.2 (1)	C5—C6—C7—N2	72.3 (2)
N3—Ni1—O1—C6	135.9 (1)	O2—C6—C7—C8	16.4 (3)
N4—Ni1—O1—C6	−135.5 (1)	O1—C6—C7—C8	142.6 (2)
N1—Ni1—O1—C6	45.7 (1)	C5—C6—C7—C8	−104.8 (3)
N2—Ni1—O3—C17	−138.9 (1)	N2—C7—C8—C9	−0.4 (4)
N3—Ni1—O3—C17	42.0 (1)	C6—C7—C8—C9	176.5 (2)
N4—Ni1—O3—C17	−46.2 (1)	C7—C8—C9—C10	0.7 (4)
N1—Ni1—O3—C17	132.6 (1)	C8—C9—C10—C11	−0.3 (4)
N2—Ni1—N1—C1	−125.2 (2)	C7—N2—C11—C10	0.5 (4)
N3—Ni1—N1—C1	53.2 (2)	Ni1—N2—C11—C10	−178.3 (2)
O1—Ni1—N1—C1	154.9 (2)	C9—C10—C11—N2	−0.3 (4)
O3—Ni1—N1—C1	−26.8 (2)	C16—N3—C12—C13	1.3 (4)
N2—Ni1—N1—C5	56.9 (2)	Ni1—N3—C12—C13	−176.6 (2)
N3—Ni1—N1—C5	−124.7 (2)	N3—C12—C13—C14	1.3 (4)
O1—Ni1—N1—C5	−23.0 (2)	C12—C13—C14—C15	−2.9 (4)
O3—Ni1—N1—C5	155.3 (2)	C13—C14—C15—C16	2.0 (4)
O1—Ni1—N2—C11	−157.4 (2)	C12—N3—C16—C15	−2.3 (3)
N4—Ni1—N2—C11	−55.0 (2)	Ni1—N3—C16—C15	176.0 (2)
O3—Ni1—N2—C11	22.7 (2)	C12—N3—C16—C17	176.1 (2)
N1—Ni1—N2—C11	124.7 (2)	Ni1—N3—C16—C17	−5.6 (2)
O1—Ni1—N2—C7	23.7 (2)	C14—C15—C16—N3	0.6 (4)
N4—Ni1—N2—C7	126.1 (2)	C14—C15—C16—C17	−177.6 (2)
O3—Ni1—N2—C7	−156.2 (2)	Ni1—O3—C17—O4	179.2 (2)
N1—Ni1—N2—C7	−54.3 (2)	Ni1—O3—C17—C18	59.3 (2)
O1—Ni1—N3—C12	−22.5 (2)	Ni1—O3—C17—C16	−55.3 (2)
N4—Ni1—N3—C12	−125.0 (2)	N3—C16—C17—O4	168.1 (2)
O3—Ni1—N3—C12	157.4 (2)	C15—C16—C17—O4	−13.6 (3)
N1—Ni1—N3—C12	55.3 (2)	N3—C16—C17—O3	43.2 (2)
O1—Ni1—N3—C16	159.5 (2)	C15—C16—C17—O3	−138.5 (2)
N4—Ni1—N3—C16	57.0 (2)	N3—C16—C17—C18	−69.1 (2)
O3—Ni1—N3—C16	−20.6 (2)	C15—C16—C17—C18	109.2 (3)
N1—Ni1—N3—C16	−122.7 (2)	C22—N4—C18—C19	0.0 (3)
N2—Ni1—N4—C22	−56.1 (2)	Ni1—N4—C18—C19	−178.9 (2)
N3—Ni1—N4—C22	125.5 (2)	C22—N4—C18—C17	−178.2 (2)
O1—Ni1—N4—C22	24.0 (2)	Ni1—N4—C18—C17	2.9 (2)
O3—Ni1—N4—C22	−154.2 (2)	O4—C17—C18—N4	−164.8 (2)
N2—Ni1—N4—C18	122.7 (2)	O3—C17—C18—N4	−43.3 (2)
N3—Ni1—N4—C18	−55.8 (2)	C16—C17—C18—N4	70.3 (2)
O1—Ni1—N4—C18	−157.2 (1)	O4—C17—C18—C19	17.0 (3)
O3—Ni1—N4—C18	24.6 (1)	O3—C17—C18—C19	138.5 (2)
C5—N1—C1—C2	0.2 (4)	C16—C17—C18—C19	−107.9 (2)
Ni1—N1—C1—C2	−177.6 (2)	N4—C18—C19—C20	0.0 (4)
N1—C1—C2—C3	1.6 (4)	C17—C18—C19—C20	178.1 (2)
C1—C2—C3—C4	−1.3 (4)	C18—C19—C20—C21	−0.3 (4)
C2—C3—C4—C5	−0.7 (4)	C19—C20—C21—C22	0.5 (4)
C1—N1—C5—C4	−2.3 (3)	C18—N4—C22—C21	0.2 (4)
Ni1—N1—C5—C4	175.9 (2)	Ni1—N4—C22—C21	178.84 (19)
C1—N1—C5—C6	176.7 (2)	C20—C21—C22—N4	−0.5 (4)
Ni1—N1—C5—C6	−5.1 (2)	O5—C23—C24—O7	25.7 (5)
C3—C4—C5—N1	2.6 (4)	O6—C23—C24—O7	−165.1 (3)
C3—C4—C5—C6	−176.3 (2)	C24'—C23—C24—O7	−67.2 (7)
Ni1—O1—C6—O2	−179.1 (2)	O5—C23—C24—C25	142.2 (4)
Ni1—O1—C6—C5	−59.9 (2)	O6—C23—C24—C25	−48.6 (6)
Ni1—O1—C6—C7	55.0 (2)	C24'—C23—C24—C25	49.4 (7)
N1—C5—C6—O2	167.4 (2)	O5—C23—C24'—C25'	−142.0 (6)
C4—C5—C6—O2	−13.6 (3)	O6—C23—C24'—C25'	56.1 (8)
N1—C5—C6—O1	45.3 (2)	C24—C23—C24'—C25'	−40.4 (7)
C4—C5—C6—O1	−135.7 (2)	O9—C26—C27—O10	−164.8 (3)
N1—C5—C6—C7	−68.9 (2)	O8—C26—C27—O10	20.9 (5)
C4—C5—C6—C7	110.1 (2)	C27'—C26—C27—O10	−72 (2)
C11—N2—C7—C8	−0.2 (4)	O9—C26—C27—C28	−45.0 (5)
Ni1—N2—C7—C8	178.9 (2)	O8—C26—C27—C28	140.7 (4)
C11—N2—C7—C6	−177.4 (2)	C27'—C26—C27—C28	48 (2)
Ni1—N2—C7—C6	1.6 (2)	O9—C26—C27'—C28'	59 (1)
O2—C6—C7—N2	−166.5 (2)	O8—C26—C27'—C28'	−141 (1)
O1—C6—C7—N2	−40.2 (3)	C27—C26—C27'—C28'	−41 (1)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1o···O6	0.85	1.67	2.494 (3)	164
O2—H2o···O5	0.85	1.77	2.617 (3)	174
O3—H3o···O8^i	0.85	1.73	2.561 (2)	167
O4—H4o···O9^i	0.85	1.76	2.605 (3)	174
O7—H7o···O8	0.85	2.29	2.999 (3)	141
O10—H10o···O5	0.85	2.20	2.967 (3)	150

Symmetry code: (i) −x+3/2, y−1/2, −z+3/2.