{[N,N′-Bis(4-methoxy­benz­yl)ethane-1,2-diyldiimino]diacetato}bis­(1H-imidazole-κN³)nickel(II)

In the title complex, [Ni(C₂₂H₂₆N₂O₄)(C₃H₄N₂)₂], the Ni atom is in a distorted octa­hedral coordination environment defined by an N₄O₂ donor set. The asymmetric unit consists of two half-molecules; each Ni atom lies on a crystallographic twofold rotation axis. In the crystal structure, hydrogen bonds link two kinds of coordination geometry around the Ni atom.

Key indicators

• Single-crystal X-ray study
• T = 297 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.050
• wR factor = 0.131
• Data-to-parameter ratio = 16.3

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT230_ALERT_2_B Hirshfeld Test Diff for    C2     -   C3      ..       9.68 su
PLAT601_ALERT_2_B Structure Contains Solvent Accessible VOIDS of .     102.00 A   3 

Alert level C
CRYSC01_ALERT_1_C The word below has not been recognised as a standard
            identifier.
            yelow
CRYSC01_ALERT_1_C No recognised colour has been given for crystal colour.
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       2.10
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.77 Ratio
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.48 Ratio
PLAT230_ALERT_2_C Hirshfeld Test Diff for    O2     -   C11     ..       6.58 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for    O6     -   C25     ..       6.17 su
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C22
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         C2
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         N4
PLAT360_ALERT_2_C Short  C(sp3)-C(sp3) Bond  C23    -   C23_b  ...       1.37 Ang.
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #        115
            O2  -NI1 -O2  -C11    63.90  0.20   2.655   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #        124
            O6  -NI2 -O6  -C25   -54.90  0.20   2.555   1.555   1.555   1.555

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

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
  10 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
   2 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

---

Computing details

Data collection: SMART (Bruker, 2001); cell refinement: SMART; data reduction: SAINT-Plus (Bruker, 2001)'; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: PLATON.

{[N,N'-Bis(4-methoxybenzyl)ethane-1,2-diyldiimino]diacetato}bis(1H-imidazole- κN³)nickel(II)

Crystal data

[Ni(C22H26N2O4)(C3H4N2)2]	F(000) = 2560
Mr = 609.32	Dx = 1.308 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 5910 reflections
a = 26.0085 (12) Å	θ = 2.2–22.2°
b = 16.4458 (8) Å	µ = 0.68 mm^−1
c = 15.0304 (7) Å	T = 297 K
β = 105.786 (1)°	Plate, yelow
V = 6186.5 (5) Å^3	0.20 × 0.10 × 0.04 mm
Z = 8

Data collection

Bruker SMART CCD area-detector diffractometer	6063 independent reflections
Radiation source: fine-focus sealed tube	3702 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.089
φ and ω scans	θmax = 26.0°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 2001)	h = −32→32
Tmin = 0.823, Tmax = 0.967	k = −20→20
32089 measured reflections	l = −18→18

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)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.131	H-atom parameters constrained
S = 0.89	w = 1/[σ^2(Fo^2) + (0.0755P)^2] where P = (Fo^2 + 2Fc^2)/3
6063 reflections	(Δ/σ)max < 0.001
373 parameters	Δρmax = 0.62 e Å^−3
0 restraints	Δρmin = −0.30 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	0.5000	0.10079 (3)	0.2500	0.04907 (17)
Ni2	0.0000	0.10195 (3)	0.2500	0.04612 (16)
C1	0.2829 (2)	0.5225 (4)	−0.0889 (4)	0.155 (2)
H1A	0.3089	0.5539	−0.0447	0.233*
H1B	0.2509	0.5540	−0.1114	0.233*
H1C	0.2969	0.5082	−0.1396	0.233*
C2	0.31324 (17)	0.3988 (3)	−0.0113 (3)	0.0860 (11)
C3	0.36580 (18)	0.4099 (2)	−0.0066 (2)	0.0790 (11)
H3	0.3769	0.4575	−0.0291	0.095*
C4	0.40335 (15)	0.3491 (2)	0.0324 (2)	0.0672 (9)
H4	0.4393	0.3573	0.0365	0.081*
C5	0.38738 (13)	0.27787 (18)	0.0644 (2)	0.0598 (8)
C6	0.33375 (14)	0.2710 (2)	0.0584 (3)	0.0862 (11)
H6	0.3216	0.2239	0.0802	0.103*
C7	0.29735 (16)	0.3311 (3)	0.0214 (3)	0.1000 (13)
H7	0.2615	0.3242	0.0194	0.120*
C8	0.42567 (12)	0.20880 (18)	0.10153 (18)	0.0597 (8)
H8A	0.4089	0.1584	0.0752	0.072*
H8B	0.4572	0.2162	0.0798	0.072*
C9	0.47143 (11)	0.27315 (17)	0.2510 (2)	0.0583 (8)
H9A	0.4697	0.2747	0.3146	0.070*
H9B	0.4538	0.3214	0.2200	0.070*
C10	0.39862 (11)	0.18009 (19)	0.2429 (2)	0.0591 (8)
H10A	0.3734	0.1457	0.1996	0.071*
H10B	0.3803	0.2298	0.2507	0.071*
C11	0.41722 (13)	0.13687 (18)	0.3352 (2)	0.0581 (8)
C12	0.45091 (12)	−0.01497 (17)	0.0942 (2)	0.0560 (7)
H12	0.4784	−0.0025	0.0678	0.067*
C13	0.40154 (12)	−0.01913 (18)	0.1862 (2)	0.0610 (8)
H13	0.3882	−0.0099	0.2368	0.073*
C14	0.37888 (12)	−0.06757 (18)	0.1135 (2)	0.0640 (8)
H14	0.3475	−0.0973	0.1046	0.077*
C15	0.22844 (16)	0.5147 (3)	0.1376 (3)	0.1124 (15)
H15A	0.2134	0.5098	0.0720	0.169*
H15B	0.2605	0.5466	0.1500	0.169*
H15C	0.2031	0.5407	0.1643	0.169*
C16	0.19981 (13)	0.3832 (2)	0.1743 (2)	0.0651 (8)
C17	0.21318 (14)	0.3097 (2)	0.2153 (3)	0.0817 (10)
H17	0.2490	0.2983	0.2432	0.098*
C18	0.17544 (14)	0.2520 (2)	0.2169 (2)	0.0779 (10)
H18	0.1860	0.2023	0.2456	0.093*
C19	0.12143 (13)	0.2667 (2)	0.1761 (2)	0.0626 (8)
C20	0.10852 (13)	0.3416 (2)	0.1336 (2)	0.0676 (9)
H20	0.0728	0.3537	0.1056	0.081*
C21	0.14668 (13)	0.3984 (2)	0.1317 (2)	0.0663 (9)
H21	0.1367	0.4476	0.1014	0.080*
C22	0.07984 (13)	0.2025 (2)	0.1762 (2)	0.0726 (10)
H22A	0.0508	0.2092	0.1204	0.087*
H22B	0.0957	0.1497	0.1725	0.087*
C23	0.02729 (13)	0.2751 (2)	0.2646 (4)	0.1069 (15)
H23A	0.0375	0.2905	0.3293	0.128*
H23B	0.0398	0.3178	0.2311	0.128*
C24	0.09759 (13)	0.1905 (2)	0.3427 (2)	0.0658 (9)
H24A	0.1120	0.2431	0.3658	0.079*
H24B	0.1265	0.1584	0.3316	0.079*
C25	0.07634 (13)	0.14823 (19)	0.4161 (2)	0.0604 (8)
C26	0.04579 (11)	−0.02164 (17)	0.1444 (2)	0.0533 (7)
H26	0.0163	−0.0136	0.0938	0.064*
C27	0.10030 (11)	−0.01518 (18)	0.2785 (2)	0.0561 (7)
H27	0.1159	−0.0013	0.3399	0.067*
C28	0.12124 (12)	−0.06669 (18)	0.2295 (2)	0.0601 (8)
H28	0.1535	−0.0944	0.2497	0.072*
N1	0.44324 (9)	0.19975 (13)	0.20487 (15)	0.0508 (6)
N2	0.44751 (9)	0.01446 (13)	0.17336 (15)	0.0517 (6)
N3	0.41088 (10)	−0.06439 (15)	0.05610 (16)	0.0593 (6)
H3A	0.4061	−0.0898	0.0045	0.071*
N4	0.05679 (9)	0.20153 (13)	0.25613 (15)	0.0505 (6)
N5	0.05215 (9)	0.01459 (13)	0.22495 (15)	0.0490 (6)
N6	0.08600 (9)	−0.07072 (14)	0.14354 (17)	0.0569 (6)
H6A	0.0893	−0.0996	0.0977	0.068*
O1	0.27187 (13)	0.4561 (2)	−0.0492 (2)	0.1275 (11)
O2	0.46337 (8)	0.10519 (11)	0.35580 (13)	0.0569 (5)
O3	0.38539 (9)	0.13307 (15)	0.38345 (16)	0.0792 (7)
O4	0.24078 (9)	0.43522 (16)	0.17734 (18)	0.0875 (7)
O5	0.10359 (11)	0.15488 (16)	0.49770 (15)	0.0990 (9)
O6	0.03467 (7)	0.10799 (11)	0.39031 (12)	0.0526 (5)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Ni1	0.0523 (3)	0.0536 (3)	0.0417 (3)	0.000	0.0134 (2)	0.000
Ni2	0.0459 (3)	0.0516 (3)	0.0412 (3)	0.000	0.0124 (2)	0.000
C1	0.170 (5)	0.145 (5)	0.161 (5)	0.039 (4)	0.063 (4)	0.078 (4)
C2	0.085 (3)	0.100 (3)	0.067 (2)	0.020 (2)	0.010 (2)	0.014 (2)
C3	0.138 (4)	0.055 (2)	0.051 (2)	0.002 (2)	0.037 (2)	0.0122 (15)
C4	0.088 (2)	0.069 (2)	0.0465 (18)	−0.0070 (19)	0.0215 (17)	0.0040 (16)
C5	0.068 (2)	0.061 (2)	0.0434 (16)	−0.0032 (16)	0.0031 (15)	0.0013 (14)
C6	0.076 (3)	0.072 (2)	0.090 (3)	−0.010 (2)	−0.013 (2)	0.023 (2)
C7	0.075 (3)	0.091 (3)	0.117 (3)	0.000 (2)	−0.002 (2)	0.028 (3)
C8	0.069 (2)	0.064 (2)	0.0401 (16)	−0.0012 (16)	0.0056 (14)	−0.0009 (15)
C9	0.0662 (18)	0.0509 (17)	0.0511 (17)	0.0054 (14)	0.0046 (15)	−0.0027 (14)
C10	0.0579 (18)	0.0644 (19)	0.0543 (18)	0.0104 (15)	0.0138 (15)	0.0055 (15)
C11	0.068 (2)	0.0564 (19)	0.0521 (18)	0.0060 (16)	0.0191 (16)	−0.0002 (15)
C12	0.0598 (19)	0.0580 (18)	0.0547 (18)	−0.0091 (15)	0.0233 (15)	−0.0023 (15)
C13	0.0611 (19)	0.0595 (19)	0.068 (2)	−0.0016 (16)	0.0268 (16)	0.0011 (17)
C14	0.0516 (18)	0.0577 (19)	0.082 (2)	−0.0070 (15)	0.0177 (17)	−0.0009 (18)
C15	0.091 (3)	0.088 (3)	0.160 (4)	−0.027 (2)	0.037 (3)	0.021 (3)
C16	0.064 (2)	0.076 (2)	0.060 (2)	−0.0142 (18)	0.0249 (17)	−0.0016 (17)
C17	0.055 (2)	0.098 (3)	0.091 (3)	−0.006 (2)	0.0179 (19)	0.017 (2)
C18	0.075 (2)	0.075 (2)	0.090 (3)	−0.0013 (19)	0.034 (2)	0.017 (2)
C19	0.064 (2)	0.082 (2)	0.0471 (17)	−0.0176 (17)	0.0237 (15)	−0.0050 (16)
C20	0.0592 (19)	0.098 (3)	0.0451 (17)	−0.0174 (19)	0.0142 (15)	0.0095 (17)
C21	0.072 (2)	0.075 (2)	0.057 (2)	−0.0079 (18)	0.0238 (17)	0.0098 (16)
C22	0.081 (2)	0.094 (3)	0.0490 (18)	−0.029 (2)	0.0280 (17)	−0.0034 (18)
C23	0.079 (2)	0.050 (2)	0.205 (5)	0.0015 (17)	0.062 (3)	0.010 (3)
C24	0.070 (2)	0.075 (2)	0.0499 (18)	−0.0249 (17)	0.0126 (16)	0.0016 (16)
C25	0.069 (2)	0.065 (2)	0.0461 (18)	−0.0117 (17)	0.0125 (15)	0.0002 (15)
C26	0.0497 (17)	0.0565 (17)	0.0524 (18)	0.0035 (14)	0.0119 (14)	0.0038 (14)
C27	0.0518 (18)	0.0610 (19)	0.0501 (17)	0.0027 (15)	0.0050 (14)	0.0038 (15)
C28	0.0495 (17)	0.0640 (19)	0.066 (2)	0.0102 (15)	0.0134 (16)	0.0102 (16)
N1	0.0560 (14)	0.0537 (14)	0.0396 (12)	0.0019 (11)	0.0075 (11)	0.0010 (11)
N2	0.0541 (15)	0.0525 (14)	0.0503 (14)	−0.0016 (11)	0.0175 (11)	0.0019 (11)
N3	0.0661 (16)	0.0594 (16)	0.0509 (15)	−0.0066 (13)	0.0135 (13)	−0.0048 (12)
N4	0.0506 (14)	0.0560 (15)	0.0469 (13)	−0.0026 (11)	0.0167 (11)	0.0039 (11)
N5	0.0494 (14)	0.0545 (14)	0.0430 (13)	−0.0009 (11)	0.0127 (11)	0.0035 (11)
N6	0.0641 (16)	0.0549 (15)	0.0568 (16)	0.0090 (13)	0.0252 (13)	0.0004 (12)
O1	0.139 (3)	0.121 (3)	0.126 (3)	0.041 (2)	0.042 (2)	0.044 (2)
O2	0.0564 (13)	0.0678 (13)	0.0485 (11)	0.0159 (10)	0.0176 (10)	0.0065 (9)
O3	0.0719 (15)	0.1016 (17)	0.0749 (16)	0.0283 (13)	0.0383 (13)	0.0258 (13)
O4	0.0662 (15)	0.0924 (18)	0.104 (2)	−0.0232 (14)	0.0241 (14)	0.0032 (15)
O5	0.1096 (19)	0.129 (2)	0.0465 (14)	−0.0640 (17)	0.0013 (13)	0.0076 (14)
O6	0.0519 (12)	0.0601 (12)	0.0447 (11)	−0.0128 (10)	0.0112 (9)	−0.0015 (9)

Geometric parameters (Å, º)

Ni1—O2	2.0655 (18)	C13—C14	1.351 (4)
Ni1—O2^i	2.0655 (18)	C13—N2	1.377 (3)
Ni1—N2	2.086 (2)	C13—H13	0.9300
Ni1—N2^i	2.086 (2)	C14—N3	1.353 (4)
Ni1—N1^i	2.178 (2)	C14—H14	0.9300
Ni1—N1	2.178 (2)	C15—O4	1.436 (5)
Ni2—O6	2.0581 (18)	C15—H15A	0.9600
Ni2—O6^ii	2.0581 (18)	C15—H15B	0.9600
Ni2—N5	2.079 (2)	C15—H15C	0.9600
Ni2—N5^ii	2.079 (2)	C16—O4	1.358 (4)
Ni2—N4^ii	2.190 (2)	C16—C17	1.358 (5)
Ni2—N4	2.190 (2)	C16—C21	1.379 (4)
C1—O1	1.313 (5)	C17—C18	1.370 (4)
C1—H1A	0.9600	C17—H17	0.9300
C1—H1B	0.9600	C18—C19	1.393 (4)
C1—H1C	0.9600	C18—H18	0.9300
C2—C7	1.328 (5)	C19—C20	1.387 (4)
C2—C3	1.362 (5)	C19—C22	1.511 (4)
C2—O1	1.427 (4)	C20—C21	1.369 (4)
C3—C4	1.409 (5)	C20—H20	0.9300
C3—H3	0.9300	C21—H21	0.9300
C4—C5	1.372 (4)	C22—N4	1.482 (3)
C4—H4	0.9300	C22—H22A	0.9700
C5—C6	1.378 (4)	C22—H22B	0.9700
C5—C8	1.514 (4)	C23—C23^ii	1.367 (7)
C6—C7	1.377 (5)	C23—N4	1.456 (4)
C6—H6	0.9300	C23—H23A	0.9700
C7—H7	0.9300	C23—H23B	0.9700
C8—N1	1.503 (3)	C24—N4	1.449 (3)
C8—H8A	0.9700	C24—C25	1.529 (4)
C8—H8B	0.9700	C24—H24A	0.9700
C9—N1	1.483 (3)	C24—H24B	0.9700
C9—C9^i	1.495 (6)	C25—O6	1.239 (3)
C9—H9A	0.9700	C25—O5	1.243 (4)
C9—H9B	0.9700	C26—N5	1.319 (3)
C10—N1	1.462 (3)	C26—N6	1.324 (3)
C10—C11	1.516 (4)	C26—H26	0.9300
C10—H10A	0.9700	C27—C28	1.332 (4)
C10—H10B	0.9700	C27—N5	1.381 (3)
C11—O3	1.242 (3)	C27—H27	0.9300
C11—O2	1.267 (3)	C28—N6	1.367 (4)
C12—N2	1.310 (3)	C28—H28	0.9300
C12—N3	1.322 (3)	N3—H3A	0.8600
C12—H12	0.9300	N6—H6A	0.8600
O2—Ni1—O2^i	175.98 (11)	N3—C14—H14	126.7
O2—Ni1—N2	94.55 (8)	O4—C15—H15A	109.5
O2^i—Ni1—N2	88.19 (8)	O4—C15—H15B	109.5
O2—Ni1—N2^i	88.19 (8)	H15A—C15—H15B	109.5
O2^i—Ni1—N2^i	94.55 (8)	O4—C15—H15C	109.5
N2—Ni1—N2^i	94.21 (12)	H15A—C15—H15C	109.5
O2—Ni1—N1^i	98.60 (8)	H15B—C15—H15C	109.5
O2^i—Ni1—N1^i	78.35 (8)	O4—C16—C17	116.3 (3)
N2—Ni1—N1^i	165.24 (8)	O4—C16—C21	125.4 (3)
N2^i—Ni1—N1^i	92.88 (8)	C17—C16—C21	118.2 (3)
O2—Ni1—N1	78.35 (8)	C16—C17—C18	121.9 (3)
O2^i—Ni1—N1	98.60 (8)	C16—C17—H17	119.1
N2—Ni1—N1	92.88 (8)	C18—C17—H17	119.1
N2^i—Ni1—N1	165.24 (8)	C17—C18—C19	120.9 (3)
N1^i—Ni1—N1	83.29 (12)	C17—C18—H18	119.5
O6—Ni2—O6^ii	174.46 (10)	C19—C18—H18	119.5
O6—Ni2—N5	95.36 (8)	C20—C19—C18	116.5 (3)
O6^ii—Ni2—N5	88.47 (8)	C20—C19—C22	122.5 (3)
O6—Ni2—N5^ii	88.47 (8)	C18—C19—C22	121.0 (3)
O6^ii—Ni2—N5^ii	95.36 (8)	C21—C20—C19	122.0 (3)
N5—Ni2—N5^ii	92.59 (12)	C21—C20—H20	119.0
O6—Ni2—N4^ii	96.28 (8)	C19—C20—H20	119.0
O6^ii—Ni2—N4^ii	79.53 (8)	C20—C21—C16	120.5 (3)
N5—Ni2—N4^ii	167.05 (8)	C20—C21—H21	119.7
N5^ii—Ni2—N4^ii	93.36 (8)	C16—C21—H21	119.7
O6—Ni2—N4	79.53 (8)	N4—C22—C19	117.1 (3)
O6^ii—Ni2—N4	96.28 (8)	N4—C22—H22A	108.0
N5—Ni2—N4	93.36 (8)	C19—C22—H22A	108.0
N5^ii—Ni2—N4	167.05 (8)	N4—C22—H22B	108.0
N4^ii—Ni2—N4	83.22 (12)	C19—C22—H22B	108.0
O1—C1—H1A	109.5	H22A—C22—H22B	107.3
O1—C1—H1B	109.5	C23^ii—C23—N4	119.9 (2)
H1A—C1—H1B	109.5	C23^ii—C23—H23A	107.4
O1—C1—H1C	109.5	N4—C23—H23A	107.4
H1A—C1—H1C	109.5	C23^ii—C23—H23B	107.4
H1B—C1—H1C	109.5	N4—C23—H23B	107.4
C7—C2—C3	120.1 (4)	H23A—C23—H23B	106.9
C7—C2—O1	115.1 (4)	N4—C24—C25	112.6 (2)
C3—C2—O1	124.7 (4)	N4—C24—H24A	109.1
C2—C3—C4	120.0 (3)	C25—C24—H24A	109.1
C2—C3—H3	120.0	N4—C24—H24B	109.1
C4—C3—H3	120.0	C25—C24—H24B	109.1
C5—C4—C3	120.6 (3)	H24A—C24—H24B	107.8
C5—C4—H4	119.7	O6—C25—O5	124.9 (3)
C3—C4—H4	119.7	O6—C25—C24	118.3 (3)
C4—C5—C6	116.4 (3)	O5—C25—C24	116.8 (3)
C4—C5—C8	122.6 (3)	N5—C26—N6	112.5 (3)
C6—C5—C8	121.0 (3)	N5—C26—H26	123.8
C7—C6—C5	122.7 (3)	N6—C26—H26	123.8
C7—C6—H6	118.6	C28—C27—N5	110.2 (3)
C5—C6—H6	118.6	C28—C27—H27	124.9
C2—C7—C6	120.1 (4)	N5—C27—H27	124.9
C2—C7—H7	119.9	C27—C28—N6	106.5 (3)
C6—C7—H7	119.9	C27—C28—H28	126.8
N1—C8—C5	116.1 (2)	N6—C28—H28	126.8
N1—C8—H8A	108.3	C10—N1—C9	110.0 (2)
C5—C8—H8A	108.3	C10—N1—C8	112.0 (2)
N1—C8—H8B	108.3	C9—N1—C8	112.0 (2)
C5—C8—H8B	108.3	C10—N1—Ni1	104.82 (16)
H8A—C8—H8B	107.4	C9—N1—Ni1	104.82 (15)
N1—C9—C9^i	111.00 (19)	C8—N1—Ni1	112.69 (17)
N1—C9—H9A	109.4	C12—N2—C13	104.7 (2)
C9^i—C9—H9A	109.4	C12—N2—Ni1	123.88 (19)
N1—C9—H9B	109.4	C13—N2—Ni1	131.2 (2)
C9^i—C9—H9B	109.4	C12—N3—C14	107.2 (3)
H9A—C9—H9B	108.0	C12—N3—H3A	126.4
N1—C10—C11	111.8 (2)	C14—N3—H3A	126.4
N1—C10—H10A	109.3	C24—N4—C23	107.5 (3)
C11—C10—H10A	109.3	C24—N4—C22	111.7 (2)
N1—C10—H10B	109.3	C23—N4—C22	113.6 (3)
C11—C10—H10B	109.3	C24—N4—Ni2	105.34 (16)
H10A—C10—H10B	107.9	C23—N4—Ni2	105.03 (17)
O3—C11—O2	125.1 (3)	C22—N4—Ni2	113.02 (18)
O3—C11—C10	117.4 (3)	C26—N5—C27	104.0 (2)
O2—C11—C10	117.5 (3)	C26—N5—Ni2	123.60 (19)
N2—C12—N3	112.4 (3)	C27—N5—Ni2	132.23 (19)
N2—C12—H12	123.8	C26—N6—C28	106.8 (2)
N3—C12—H12	123.8	C26—N6—H6A	126.6
C14—C13—N2	109.1 (3)	C28—N6—H6A	126.6
C14—C13—H13	125.4	C1—O1—C2	119.8 (4)
N2—C13—H13	125.4	C11—O2—Ni1	115.53 (18)
C13—C14—N3	106.5 (3)	C16—O4—C15	118.3 (3)
C13—C14—H14	126.7	C25—O6—Ni2	116.68 (18)
C7—C2—C3—C4	0.5 (6)	O2^i—Ni1—N2—C13	−170.7 (2)
O1—C2—C3—C4	−180.0 (3)	N2^i—Ni1—N2—C13	94.9 (2)
C2—C3—C4—C5	1.2 (5)	N1^i—Ni1—N2—C13	−146.6 (3)
C3—C4—C5—C6	−1.8 (4)	N1—Ni1—N2—C13	−72.1 (2)
C3—C4—C5—C8	176.2 (3)	N2—C12—N3—C14	0.3 (3)
C4—C5—C6—C7	0.8 (5)	C13—C14—N3—C12	−0.4 (3)
C8—C5—C6—C7	−177.2 (4)	C25—C24—N4—C23	83.2 (3)
C3—C2—C7—C6	−1.4 (7)	C25—C24—N4—C22	−151.5 (3)
O1—C2—C7—C6	179.0 (4)	C25—C24—N4—Ni2	−28.4 (3)
C5—C6—C7—C2	0.7 (7)	C23^ii—C23—N4—C24	−134.6 (6)
C4—C5—C8—N1	103.3 (3)	C23^ii—C23—N4—C22	101.2 (6)
C6—C5—C8—N1	−78.8 (4)	C23^ii—C23—N4—Ni2	−22.8 (7)
N1—C10—C11—O3	164.5 (3)	C19—C22—N4—C24	−58.7 (4)
N1—C10—C11—O2	−17.7 (4)	C19—C22—N4—C23	63.2 (4)
N2—C13—C14—N3	0.4 (3)	C19—C22—N4—Ni2	−177.3 (2)
O4—C16—C17—C18	180.0 (3)	O6—Ni2—N4—C24	22.63 (18)
C21—C16—C17—C18	−1.4 (5)	O6^ii—Ni2—N4—C24	−161.04 (18)
C16—C17—C18—C19	0.0 (6)	N5—Ni2—N4—C24	−72.21 (19)
C17—C18—C19—C20	0.7 (5)	N5^ii—Ni2—N4—C24	45.0 (5)
C17—C18—C19—C22	178.8 (3)	N4^ii—Ni2—N4—C24	120.3 (2)
C18—C19—C20—C21	0.0 (5)	O6—Ni2—N4—C23	−90.7 (3)
C22—C19—C20—C21	−178.1 (3)	O6^ii—Ni2—N4—C23	85.6 (3)
C19—C20—C21—C16	−1.4 (5)	N5—Ni2—N4—C23	174.4 (3)
O4—C16—C21—C20	−179.4 (3)	N5^ii—Ni2—N4—C23	−68.4 (5)
C17—C16—C21—C20	2.1 (5)	N4^ii—Ni2—N4—C23	7.0 (2)
C20—C19—C22—N4	−92.9 (4)	O6—Ni2—N4—C22	144.9 (2)
C18—C19—C22—N4	89.1 (4)	O6^ii—Ni2—N4—C22	−38.8 (2)
N4—C24—C25—O6	20.6 (4)	N5—Ni2—N4—C22	50.0 (2)
N4—C24—C25—O5	−161.8 (3)	N5^ii—Ni2—N4—C22	167.3 (3)
N5—C27—C28—N6	−0.5 (3)	N4^ii—Ni2—N4—C22	−117.4 (2)
C11—C10—N1—C9	−79.0 (3)	N6—C26—N5—C27	−0.4 (3)
C11—C10—N1—C8	155.8 (2)	N6—C26—N5—Ni2	175.61 (17)
C11—C10—N1—Ni1	33.2 (3)	C28—C27—N5—C26	0.5 (3)
C9^i—C9—N1—C10	153.4 (3)	C28—C27—N5—Ni2	−174.97 (19)
C9^i—C9—N1—C8	−81.3 (3)	O6—Ni2—N5—C26	172.1 (2)
C9^i—C9—N1—Ni1	41.2 (3)	O6^ii—Ni2—N5—C26	−11.9 (2)
C5—C8—N1—C10	63.8 (3)	N5^ii—Ni2—N5—C26	83.4 (2)
C5—C8—N1—C9	−60.3 (3)	N4^ii—Ni2—N5—C26	−33.9 (5)
C5—C8—N1—Ni1	−178.27 (19)	N4—Ni2—N5—C26	−108.1 (2)
O2—Ni1—N1—C10	−29.67 (17)	O6—Ni2—N5—C27	−13.1 (2)
O2^i—Ni1—N1—C10	152.99 (17)	O6^ii—Ni2—N5—C27	162.8 (2)
N2—Ni1—N1—C10	64.39 (17)	N5^ii—Ni2—N5—C27	−101.9 (2)
N2^i—Ni1—N1—C10	−54.3 (4)	N4^ii—Ni2—N5—C27	140.8 (3)
N1^i—Ni1—N1—C10	−129.9 (2)	N4—Ni2—N5—C27	66.6 (2)
O2—Ni1—N1—C9	86.13 (17)	N5—C26—N6—C28	0.1 (3)
O2^i—Ni1—N1—C9	−91.21 (17)	C27—C28—N6—C26	0.2 (3)
N2—Ni1—N1—C9	−179.81 (17)	C7—C2—O1—C1	−175.5 (5)
N2^i—Ni1—N1—C9	61.5 (4)	C3—C2—O1—C1	4.9 (7)
N1^i—Ni1—N1—C9	−14.12 (13)	O3—C11—O2—Ni1	167.4 (3)
O2—Ni1—N1—C8	−151.77 (19)	C10—C11—O2—Ni1	−10.2 (3)
O2^i—Ni1—N1—C8	30.89 (19)	O2^i—Ni1—O2—C11	63.9 (2)
N2—Ni1—N1—C8	−57.71 (19)	N2—Ni1—O2—C11	−68.9 (2)
N2^i—Ni1—N1—C8	−176.4 (3)	N2^i—Ni1—O2—C11	−163.0 (2)
N1^i—Ni1—N1—C8	108.0 (2)	N1^i—Ni1—O2—C11	104.3 (2)
N3—C12—N2—C13	0.0 (3)	N1—Ni1—O2—C11	23.1 (2)
N3—C12—N2—Ni1	−175.51 (18)	C17—C16—O4—C15	−177.9 (3)
C14—C13—N2—C12	−0.2 (3)	C21—C16—O4—C15	3.5 (5)
C14—C13—N2—Ni1	174.80 (19)	O5—C25—O6—Ni2	−176.4 (3)
O2—Ni1—N2—C12	−179.4 (2)	C24—C25—O6—Ni2	1.0 (4)
O2^i—Ni1—N2—C12	3.5 (2)	O6^ii—Ni2—O6—C25	−54.9 (2)
N2^i—Ni1—N2—C12	−90.9 (2)	N5—Ni2—O6—C25	78.7 (2)
N1^i—Ni1—N2—C12	27.6 (5)	N5^ii—Ni2—O6—C25	171.2 (2)
N1—Ni1—N2—C12	102.0 (2)	N4^ii—Ni2—O6—C25	−95.6 (2)
O2—Ni1—N2—C13	6.4 (2)	N4—Ni2—O6—C25	−13.7 (2)

Symmetry codes: (i) −x+1, y, −z+1/2; (ii) −x, y, −z+1/2.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3A···O3^iii	0.86	1.89	2.741 (3)	170
N6—H6A···O5^iii	0.86	1.88	2.734 (3)	173
C12—H12···O2^i	0.93	2.41	2.920 (3)	115
C26—H26···O6^ii	0.93	2.45	2.933 (3)	113

Symmetry codes: (i) −x+1, y, −z+1/2; (ii) −x, y, −z+1/2; (iii) x, −y, z−1/2.