{6,6′-Dieth­oxy-2,2′-[ethane-1,2-diyl­bis(nitrilo­methyl­idyne)]­diphenolato}­trinitratoyttrium(III)nickel(II)

The title heteronuclear Ni^II–Y^III complex (systematic name: {6,6′-dieth­oxy-2,2′-[ethane-1,2-diylbis(nitrilo­methyl­idyne)]diphenolato-1κ⁴O¹,O^1′,O⁶,O^6′:2κ⁴O¹,N,N′,O^1′}trinitrato-1κ⁶O,O′-yttrium(III)nickel(II)), [NiY(C₂₀H₂₂N₂O₄)(NO₃)₃], with the hexa­dentate Schiff base compartmental ligand N,N′-bis­(3-ethoxy­salicyl­idene)ethyl­enediamine (H₂L), has been synthesized and structurally characterized. The Ni and Y atoms are doubly bridged by two phenolate O atoms provided by the Schiff base ligand. The coordination of the Ni atom is square planar, formed by two imine N atoms and two phenolate O atoms. The Y^III atom has a decacoordination environment of O atoms, formed by the phenolate O atoms, two ethoxy O atoms and two O atoms each from three nitrate ligands. No classical inter­molecular hydrogen bonds are found. Some weak C—H...O and O...Ni inter­actions generate a two-dimensional zigzag sheet.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.028
• wR factor = 0.061
• Data-to-parameter ratio = 16.5

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT220_ALERT_2_C Large Non-Solvent    O     Ueq(max)/Ueq(min) ...       2.52 Ratio
PLAT230_ALERT_2_C Hirshfeld Test Diff for    O3     -   N3      ..       5.07 su
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Y1     -   O6      ..       8.83 su
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Y1     -   O7      ..       8.71 su
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Y1     -   O9      ..       8.09 su
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Y1     -   O10     ..       8.54 su
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Ni1    -   O1      ..       5.41 su
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         O7
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        O10
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         Y1
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         N4

Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           28.22
           From the CIF: _reflns_number_total               5977
           Count of symmetry unique reflns         3487
           Completeness (_total/calc)            171.41%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured      2490
           Fraction of Friedel pairs measured     0.714
           Are heavy atom types Z>Si present        yes
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature .        293 K
PLAT794_ALERT_5_G Check Predicted Bond Valency for Y1          (3)       3.55
PLAT794_ALERT_5_G Check Predicted Bond Valency for Ni1         (2)       2.19

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

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
  11 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
   1 ALERT type 4 Improvement, methodology, query or suggestion
   2 ALERT type 5 Informative message, check


checkCIF publication errors

Alert level A
PUBL023_ALERT_1_A There is a mismatched ^ on line 129
              1\k^2^O^1^,O^1'^,O^6^,O^6'^:2\k^2^O^1^,N,N',O^1'^}trinitrato-1\k^O,O'-
              If you require a ^ then it should be escaped
              with a \, i.e. \^
              Otherwise there must be a matching closing ~, e.g. ^12^C
PUBL023_ALERT_1_A There is a mismatched ^ on line 262
              1\k^2^O^1^,O^1'^,O^6^,O^6'^:2\k^2^O^1^,N,N',O^1'^}trinitrato-1\k^O,O'-
              If you require a ^ then it should be escaped
              with a \, i.e. \^
              Otherwise there must be a matching closing ~, e.g. ^12^C

   2 ALERT level A = Data missing that is essential or data in wrong format
   0 ALERT level G = General alerts. Data that may be required is missing

---

S1. Comment

The potential applications of trivalent lanthanide complexes as contrast agent for magnetic resonance imaging and stains for fluorescence imaging have prompted considerable interest in the preparation, magnetic and optical properties of 3 d-4f hetorometallic dinuclear complexes (Baggio et al., 2000; Caravan et al., 1999; Edder et al., 2000). Recently, some 3 d-4f hetorometallic Schiff base complexes have been synthesized, such as Cu^II—Gd^III, Ni^II—Gd^III and Zn^II—Ho^III heterodinuclear complexes (Brewer et al., 2001; Mohanta et al., 2002; Wong et al., 2002), which exhibits novel magnetic and luminescent properties, As part of our investigations into the structure and applications of 3 d-4f hetorometallic Schiff base complexes, we report here the synthesis and X-ray crystal structure analysis of the title complex, (I), a new Ni^II—Y^III complex with salen-type Schiff base N,N'-bis(3-ethoxysalicylidene)ethylenediamine(H₂L).

Complex (I) crystallizes in the space group P2₁2₁2₁, with nickel and yttrium doubly bridged by two phenolate O atoms provided by a salen-type Schiff base ligand. The inner salen-type cavity is occupied by nickel(II), while yttrium(III) is present in the open and larger portion of the dinucleating compartmental Schiff base ligand. The dihedral angles between the mean planes of Ni1/O1/O2 and Y1/O1/O2 is 4.1 (2)° suggesting that the bridging moiety is almost planar; the deviation of atoms from the least squares Ni1/O1/O2/Y1 plane being -0.0340 (3)Å for Ni, -0.0244 (2)Å for Y, 0.096 (3)Å for O1 and 0.0287 (3)Å for O2.

The yttrium(III) center in (I) has a decacoordination environment of O atoms. In addition to the phenolate ligands, two ethoxy O atoms coordinate to this metal center, two O atoms each from the three nitrates chelate to yttrium to complete the decacoordination. The three kinds of Y—O bond distances are significantly different, the shortest being the Y—O(phenolate) and longest being the Y—O(ethoxy) separations.

The coordination of nickel(II) is square planar. The donor centers are alternatively above and below the mean N₂O₂ plane with an average deviation from the plane of 0.0782 (2) Å, while Ni1 is 0.0423 (3)Å above this square plane.

Adjacent molecules are held together by weak interactions (O8···Ni1 = 3.146 (4) Å, C9—H9B···O4ⁱ = 3.278 (4) and C7—H7···O4ⁱⁱ = 3.293 (4); symmetry codes:(i)x - 1, y, z; (ii)-x, y - 1/2, 3/2 - z). these link the molecules into a two-dimensional zigzag sheet (Fig 2).

Related literature

For related literature, see: Baggio et al. (2000); Brewer et al. (2001); Caravan et al. (1999); Edder et al. (2000); Mohanta et al. (2002); Wong et al. (2002).

S2. Experimental

H₂L was prepared by the 2:1 condensation of 3-ethoxysalicylaldehyde and ethylenediamine in methanol. Complex (I) was obtained by the treatment of nickel(II) acetate tetrahydrate (0.217 g, 1 mmol) with H₂L(0.356 g, 1 mmol) in methanol solution (50 ml) under reflux for 3 h and then for another 3 h after the addition of yttrium(III) nitrate hexahydrate (0.383 g, 1 mmol). The reaction mixture was cooled and the resulting precipitate was filtered off, washed with diethyl ether and dried in vacuo. Single crystals of (I) suitable for X-ray analysis were obtained by slow evaporation at room temperature of a methanol solution. Analysis calculated for C₂₀H₂₂N₅NiO₁₃Y: C 31.94, H 3.22, N 10.18, Ni 8.53, Y 12.92%; found: C 31.92, H 3.15, N 10.20, Ni 8.50, Y 12.90%. IR (KBr, cm^-1): 1640 (C=N), 1384, 1491 (nitrate).

S3. Refinement

The H atoms were positioned geometrically and treated as riding on their parent atoms, with C—H distances of 0.97 (methylene) and 0.96 Å (methyl), and with U_iso(H) = 1.5U_eq(C) for methyl H atoms and 1.2U_eq(C) for other H atoms.

Computing details

Data collection: APEX2 (Bruker, 2004); cell refinement: APEX2; data reduction: APEX2; program(s) used to solve structure: APEX2; program(s) used to refine structure: APEX2; molecular graphics: APEX2; software used to prepare material for publication: APEX2.

Figures

	Fig. 1. The molecular structure of (I), showing 30% probability displacement ellipsoids. All the H atoms on carbon have been omitted for clarity.
	Fig. 2. The packing diagram of (I), viewed along the b axis; hydrogen bonds are shown as dashed lines.

{6,6'-diethoxy-2,2'-[ethane-1,2-diylbis(nitrilomethylidyne)]diphenolato- 1κ⁴O¹,O^1',O⁶,O^6':2κ⁴O¹,N,N',O^1'}trinitrato-1κ⁶O,O'- yttrium(III)nickel(II)

Crystal data

[NiY(C20H22N2O4)(NO3)3]	F(000) = 1392
Mr = 688.05	Dx = 1.830 Mg m^−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 18612 reflections
a = 8.5837 (10) Å	θ = 1.8–28.2°
b = 13.7547 (16) Å	µ = 3.15 mm^−1
c = 21.153 (2) Å	T = 293 K
V = 2497.5 (5) Å^3	Block, red
Z = 4	0.32 × 0.28 × 0.19 mm

Data collection

Bruker APEXII area-detector diffractometer	5977 independent reflections
Radiation source: fine-focus sealed tube	4933 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.028
Detector resolution: 0 pixels mm^-1	θmax = 28.2°, θmin = 1.8°
φ and ω scans	h = −10→11
Absorption correction: multi-scan (SADABS; Bruker, 2004)	k = −18→18
Tmin = 0.380, Tmax = 0.559	l = −28→27
18612 measured reflections

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.028	H-atom parameters constrained
wR(F^2) = 0.061	w = 1/[σ^2(Fo^2) + (0.0001P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.98	(Δ/σ)max = 0.003
5977 reflections	Δρmax = 0.37 e Å^−3
363 parameters	Δρmin = −0.56 e Å^−3
0 restraints	Absolute structure: Flack (1983), with how many Friedel pairs?
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.011 (5)

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
Y1	0.25957 (3)	1.001598 (17)	0.899553 (11)	0.03377 (7)
Ni1	−0.06212 (4)	0.94357 (2)	0.816733 (16)	0.03396 (8)
O1	0.0443 (2)	1.05622 (12)	0.84475 (8)	0.0363 (4)
C10	−0.2219 (4)	1.1056 (2)	0.76256 (12)	0.0421 (7)
H10	−0.2938	1.1313	0.7342	0.051*
C16	−0.0176 (3)	1.14513 (16)	0.84431 (12)	0.0326 (6)
O13	0.1656 (2)	1.17532 (12)	0.92318 (8)	0.0390 (4)
C15	0.0455 (3)	1.21262 (17)	0.88636 (12)	0.0342 (6)
C2	−0.0145 (3)	0.71544 (18)	0.84982 (13)	0.0381 (6)
C11	−0.1426 (3)	1.17201 (19)	0.80476 (13)	0.0373 (6)
C7	−0.1416 (3)	0.74305 (19)	0.80946 (14)	0.0435 (7)
H7	−0.2064	0.6936	0.7951	0.052*
C1	0.0975 (3)	0.78135 (17)	0.87331 (12)	0.0349 (6)
C6	0.2204 (3)	0.74670 (17)	0.90983 (12)	0.0362 (6)
C17	0.2364 (4)	1.23942 (19)	0.97003 (12)	0.0447 (7)
H17A	0.2896	1.2004	1.0015	0.054*
H17B	0.1551	1.2759	0.9913	0.054*
C4	0.1187 (4)	0.58477 (19)	0.90364 (15)	0.0527 (8)
H4	0.1246	0.5194	0.9146	0.063*
C3	−0.0007 (4)	0.61647 (19)	0.86702 (14)	0.0487 (8)
H3	−0.0749	0.5722	0.8529	0.058*
C18	0.3505 (4)	1.3092 (2)	0.94085 (16)	0.0582 (9)
H18A	0.2967	1.3515	0.9121	0.087*
H18B	0.4290	1.2735	0.9184	0.087*
H18C	0.3987	1.3472	0.9735	0.087*
C13	−0.1360 (4)	1.3332 (2)	0.85042 (15)	0.0509 (8)
H13	−0.1756	1.3960	0.8526	0.061*
C12	−0.1973 (4)	1.2684 (2)	0.80845 (15)	0.0484 (8)
H12	−0.2771	1.2883	0.7816	0.058*
C14	−0.0143 (4)	1.30548 (18)	0.89000 (14)	0.0442 (7)
H14	0.0267	1.3496	0.9189	0.053*
O9	0.2877 (3)	1.00638 (16)	1.01235 (9)	0.0548 (5)
O5	0.3602 (2)	1.11027 (13)	0.81731 (10)	0.0498 (5)
O2	0.0936 (2)	0.87691 (12)	0.86291 (9)	0.0411 (5)
N1	−0.1987 (3)	1.01332 (16)	0.76193 (10)	0.0402 (5)
O10	0.0577 (3)	0.97519 (16)	0.97990 (10)	0.0596 (6)
O12	0.3210 (2)	0.81926 (12)	0.92998 (9)	0.0408 (5)
N5	0.1451 (3)	0.99281 (18)	1.02646 (12)	0.0489 (6)
O3	0.3174 (3)	0.96332 (15)	0.78781 (10)	0.0537 (6)
N3	0.3590 (3)	1.0473 (2)	0.77296 (12)	0.0495 (6)
O6	0.5317 (3)	0.96367 (14)	0.88673 (11)	0.0548 (5)
O7	0.4993 (3)	1.09272 (18)	0.94041 (11)	0.0682 (7)
C19	0.4573 (4)	0.7890 (2)	0.96537 (13)	0.0467 (7)
H19A	0.4264	0.7413	0.9967	0.056*
H19B	0.4997	0.8448	0.9876	0.056*
N2	−0.1735 (3)	0.82995 (16)	0.79151 (10)	0.0389 (6)
C9	−0.2765 (4)	0.9463 (2)	0.71762 (13)	0.0469 (7)
H9A	−0.2093	0.9333	0.6817	0.056*
H9B	−0.3724	0.9751	0.7022	0.056*
N4	0.5926 (3)	1.0332 (2)	0.91780 (13)	0.0536 (7)
C5	0.2324 (4)	0.64897 (19)	0.92502 (13)	0.0462 (7)
H5	0.3154	0.6266	0.9492	0.055*
C20	0.5803 (4)	0.7464 (2)	0.92445 (16)	0.0607 (9)
H20A	0.6188	0.7953	0.8960	0.091*
H20B	0.5374	0.6935	0.9006	0.091*
H20C	0.6642	0.7230	0.9503	0.091*
O11	0.0986 (3)	0.99550 (19)	1.08050 (11)	0.0783 (8)
O8	0.7340 (3)	1.0388 (2)	0.92367 (13)	0.0916 (9)
O4	0.3972 (3)	1.0700 (2)	0.71906 (11)	0.0833 (9)
C8	−0.3115 (4)	0.8526 (2)	0.75264 (14)	0.0473 (7)
H8A	−0.4025	0.8606	0.7793	0.057*
H8B	−0.3314	0.8004	0.7229	0.057*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Y1	0.03256 (14)	0.02959 (11)	0.03916 (12)	−0.00066 (13)	−0.00454 (10)	−0.00200 (11)
Ni1	0.03277 (19)	0.02569 (14)	0.04342 (17)	−0.00143 (14)	−0.01103 (16)	−0.00396 (14)
O1	0.0352 (10)	0.0254 (8)	0.0483 (10)	0.0021 (8)	−0.0072 (8)	−0.0038 (8)
C10	0.0387 (18)	0.0466 (16)	0.0410 (15)	0.0092 (14)	−0.0048 (12)	−0.0015 (12)
C16	0.0349 (16)	0.0253 (12)	0.0377 (13)	0.0029 (10)	0.0047 (11)	−0.0004 (10)
O13	0.0424 (12)	0.0289 (9)	0.0456 (11)	−0.0013 (8)	−0.0055 (9)	−0.0074 (8)
C15	0.0331 (15)	0.0291 (12)	0.0402 (14)	−0.0009 (11)	0.0026 (12)	0.0019 (10)
C2	0.0400 (17)	0.0309 (12)	0.0433 (15)	−0.0048 (12)	0.0069 (13)	−0.0064 (12)
C11	0.0334 (16)	0.0357 (13)	0.0429 (16)	0.0025 (12)	−0.0032 (12)	−0.0005 (12)
C7	0.0417 (19)	0.0394 (15)	0.0494 (18)	−0.0107 (13)	0.0030 (14)	−0.0148 (13)
C1	0.0405 (17)	0.0259 (12)	0.0383 (14)	−0.0012 (11)	0.0039 (12)	−0.0013 (10)
C6	0.0403 (17)	0.0294 (12)	0.0390 (14)	0.0021 (11)	0.0051 (12)	0.0000 (10)
C17	0.055 (2)	0.0381 (14)	0.0409 (15)	−0.0038 (15)	−0.0079 (14)	−0.0088 (11)
C4	0.071 (2)	0.0272 (13)	0.0594 (19)	0.0013 (13)	0.0117 (17)	0.0040 (13)
C3	0.064 (2)	0.0268 (13)	0.0552 (18)	−0.0091 (14)	0.0070 (15)	−0.0060 (12)
C18	0.057 (2)	0.0402 (16)	0.077 (2)	−0.0083 (15)	−0.0175 (18)	0.0010 (16)
C13	0.047 (2)	0.0308 (14)	0.075 (2)	0.0094 (14)	0.0026 (16)	−0.0015 (14)
C12	0.0432 (19)	0.0398 (14)	0.062 (2)	0.0097 (13)	−0.0072 (15)	0.0051 (14)
C14	0.0482 (19)	0.0293 (13)	0.0551 (17)	−0.0003 (12)	0.0054 (14)	−0.0092 (12)
O9	0.0576 (15)	0.0562 (12)	0.0505 (11)	−0.0074 (12)	−0.0091 (10)	−0.0025 (10)
O5	0.0527 (14)	0.0427 (10)	0.0541 (12)	0.0036 (9)	0.0056 (11)	0.0048 (11)
O2	0.0421 (13)	0.0247 (8)	0.0565 (12)	−0.0014 (8)	−0.0142 (9)	−0.0018 (8)
N1	0.0351 (13)	0.0417 (13)	0.0437 (13)	0.0018 (11)	−0.0075 (9)	−0.0044 (11)
O10	0.0507 (13)	0.0757 (16)	0.0522 (12)	−0.0048 (12)	−0.0020 (11)	0.0029 (10)
O12	0.0376 (12)	0.0344 (10)	0.0503 (12)	0.0038 (8)	−0.0097 (9)	0.0000 (8)
N5	0.0618 (18)	0.0365 (12)	0.0484 (15)	−0.0012 (14)	0.0047 (12)	0.0043 (12)
O3	0.0576 (15)	0.0544 (13)	0.0491 (12)	0.0010 (11)	−0.0020 (10)	−0.0117 (10)
N3	0.0395 (15)	0.0683 (17)	0.0408 (15)	0.0204 (14)	−0.0014 (11)	0.0085 (14)
O6	0.0433 (13)	0.0440 (11)	0.0772 (14)	−0.0010 (10)	−0.0049 (11)	−0.0021 (10)
O7	0.0563 (17)	0.0776 (17)	0.0709 (16)	−0.0113 (13)	−0.0022 (12)	−0.0279 (13)
C19	0.0417 (18)	0.0483 (16)	0.0501 (17)	0.0057 (15)	−0.0081 (14)	0.0042 (13)
N2	0.0347 (14)	0.0368 (12)	0.0451 (13)	−0.0033 (11)	−0.0018 (10)	−0.0098 (10)
C9	0.0425 (18)	0.0510 (15)	0.0473 (15)	0.0054 (15)	−0.0115 (13)	−0.0132 (13)
N4	0.0434 (17)	0.0622 (17)	0.0552 (15)	−0.0102 (13)	−0.0036 (13)	0.0076 (13)
C5	0.054 (2)	0.0352 (14)	0.0495 (16)	0.0057 (14)	0.0043 (15)	0.0059 (12)
C20	0.048 (2)	0.055 (2)	0.079 (2)	0.0133 (17)	0.0066 (17)	0.0102 (16)
O11	0.112 (2)	0.0727 (15)	0.0500 (13)	−0.0111 (17)	0.0180 (13)	0.0028 (13)
O8	0.0366 (15)	0.134 (2)	0.1042 (19)	−0.0233 (16)	−0.0113 (13)	0.0043 (18)
O4	0.083 (2)	0.120 (2)	0.0471 (13)	0.0460 (18)	0.0175 (12)	0.0218 (14)
C8	0.0385 (18)	0.0504 (17)	0.0531 (18)	−0.0053 (14)	−0.0102 (14)	−0.0131 (14)

Geometric parameters (Å, º)

Y1—O1	2.3073 (17)	C4—C3	1.356 (4)
Y1—O2	2.3602 (18)	C4—C5	1.392 (4)
Y1—O3	2.472 (2)	C4—H4	0.9300
Y1—O5	2.451 (2)	C3—H3	0.9300
Y1—O6	2.409 (2)	C18—H18A	0.9600
Y1—O7	2.560 (2)	C18—H18B	0.9600
Y1—O9	2.399 (2)	C18—H18C	0.9600
Y1—O10	2.454 (2)	C13—C12	1.364 (4)
Y1—O12	2.6424 (17)	C13—C14	1.392 (4)
Y1—O13	2.5708 (17)	C13—H13	0.9300
Ni1—O1	1.8938 (17)	C12—H12	0.9300
Ni1—O2	1.8927 (18)	C14—H14	0.9300
Ni1—N1	1.907 (2)	O9—N5	1.274 (3)
Ni1—N2	1.908 (2)	O5—N3	1.276 (3)
O1—C16	1.333 (3)	N1—C9	1.475 (3)
C10—N1	1.286 (3)	O10—N5	1.262 (3)
C10—C11	1.447 (4)	O12—C19	1.450 (3)
C10—H10	0.9300	N5—O11	1.211 (3)
C16—C15	1.395 (4)	O3—N3	1.250 (3)
C16—C11	1.410 (4)	N3—O4	1.227 (3)
O13—C15	1.390 (3)	O6—N4	1.272 (3)
O13—C17	1.459 (3)	O7—N4	1.242 (3)
C15—C14	1.379 (3)	C19—C20	1.486 (4)
C2—C1	1.412 (4)	C19—H19A	0.9700
C2—C3	1.414 (4)	C19—H19B	0.9700
C2—C7	1.436 (4)	N2—C8	1.475 (4)
C11—C12	1.408 (4)	C9—C8	1.517 (4)
C7—N2	1.284 (3)	C9—H9A	0.9700
C7—H7	0.9300	C9—H9B	0.9700
C1—O2	1.333 (3)	N4—O8	1.223 (3)
C1—C6	1.392 (4)	C5—H5	0.9300
C6—C5	1.386 (3)	C20—H20A	0.9600
C6—O12	1.387 (3)	C20—H20B	0.9600
C17—C18	1.504 (4)	C20—H20C	0.9600
C17—H17A	0.9700	C8—H8A	0.9700
C17—H17B	0.9700	C8—H8B	0.9700
O1—Y1—O2	65.69 (6)	O13—C17—C18	112.2 (2)
O1—Y1—O3	75.50 (7)	O13—C17—H17A	109.2
O1—Y1—O5	74.16 (7)	C18—C17—H17A	109.2
O1—Y1—O6	142.25 (7)	O13—C17—H17B	109.2
O1—Y1—O7	130.85 (8)	C18—C17—H17B	109.2
O1—Y1—O9	124.85 (7)	H17A—C17—H17B	107.9
O1—Y1—O10	80.25 (7)	C3—C4—C5	120.7 (3)
O1—Y1—O12	126.25 (6)	C3—C4—H4	119.6
O1—Y1—O13	62.86 (6)	C5—C4—H4	119.6
O2—Y1—O3	69.65 (7)	C4—C3—C2	121.3 (3)
O2—Y1—O5	115.01 (6)	C4—C3—H3	119.3
O2—Y1—O6	113.00 (7)	C2—C3—H3	119.3
O2—Y1—O7	162.14 (7)	C17—C18—H18A	109.5
O2—Y1—O9	114.04 (7)	C17—C18—H18B	109.5
O2—Y1—O10	72.17 (7)	H18A—C18—H18B	109.5
O2—Y1—O12	60.71 (6)	C17—C18—H18C	109.5
O2—Y1—O13	123.36 (6)	H18A—C18—H18C	109.5
O3—Y1—O7	105.42 (8)	H18B—C18—H18C	109.5
O3—Y1—O12	89.47 (7)	C12—C13—C14	120.1 (3)
O3—Y1—O13	116.54 (7)	C12—C13—H13	119.9
O5—Y1—O3	51.71 (7)	C14—C13—H13	119.9
O5—Y1—O7	69.98 (8)	C13—C12—C11	121.5 (3)
O5—Y1—O10	146.17 (7)	C13—C12—H12	119.2
O5—Y1—O12	132.95 (6)	C11—C12—H12	119.2
O5—Y1—O13	71.44 (6)	C15—C14—C13	120.0 (3)
O6—Y1—O3	69.61 (8)	C15—C14—H14	120.0
O6—Y1—O5	73.16 (7)	C13—C14—H14	120.0
O6—Y1—O7	50.55 (7)	N5—O9—Y1	97.60 (16)
O6—Y1—O10	136.94 (8)	N3—O5—Y1	96.04 (16)
O6—Y1—O12	68.19 (6)	C1—O2—Ni1	125.48 (18)
O6—Y1—O13	121.83 (7)	C1—O2—Y1	130.33 (17)
O7—Y1—O12	102.84 (7)	Ni1—O2—Y1	104.11 (7)
O7—Y1—O13	74.42 (7)	C10—N1—C9	123.6 (2)
O9—Y1—O3	159.49 (8)	C10—N1—Ni1	125.9 (2)
O9—Y1—O5	130.82 (8)	C9—N1—Ni1	110.50 (18)
O9—Y1—O6	91.16 (8)	N5—O10—Y1	95.28 (18)
O9—Y1—O7	64.52 (8)	C6—O12—C19	117.0 (2)
O9—Y1—O10	52.16 (7)	C6—O12—Y1	118.95 (15)
O9—Y1—O12	76.33 (7)	C19—O12—Y1	123.98 (16)
O9—Y1—O13	79.21 (7)	O11—N5—O10	123.1 (3)
O10—Y1—O3	140.57 (8)	O11—N5—O9	122.2 (3)
O10—Y1—O7	113.97 (7)	O10—N5—O9	114.6 (2)
O10—Y1—O12	80.31 (7)	N3—O3—Y1	95.79 (16)
O10—Y1—O13	77.38 (7)	O4—N3—O3	123.0 (3)
O13—Y1—O12	153.82 (7)	O4—N3—O5	120.6 (3)
O1—Ni1—N1	94.30 (8)	O3—N3—O5	116.4 (2)
O1—Ni1—N2	177.80 (9)	N4—O6—Y1	100.24 (18)
O2—Ni1—O1	83.93 (7)	N4—O7—Y1	93.76 (17)
O2—Ni1—N1	172.48 (10)	O12—C19—C20	112.7 (2)
O2—Ni1—N2	95.83 (9)	O12—C19—H19A	109.1
N1—Ni1—N2	86.22 (10)	C20—C19—H19A	109.1
C16—O1—Ni1	123.80 (16)	O12—C19—H19B	109.1
C16—O1—Y1	128.40 (16)	C20—C19—H19B	109.1
Ni1—O1—Y1	106.08 (7)	H19A—C19—H19B	107.8
N1—C10—C11	123.8 (3)	C7—N2—C8	122.2 (2)
N1—C10—H10	118.1	C7—N2—Ni1	124.9 (2)
C11—C10—H10	118.1	C8—N2—Ni1	112.67 (17)
O1—C16—C15	116.8 (2)	N1—C9—C8	108.1 (2)
O1—C16—C11	123.2 (2)	N1—C9—H9A	110.1
C15—C16—C11	120.0 (2)	C8—C9—H9A	110.1
C15—O13—C17	117.79 (19)	N1—C9—H9B	110.1
C15—O13—Y1	117.82 (13)	C8—C9—H9B	110.1
C17—O13—Y1	124.28 (16)	H9A—C9—H9B	108.4
C14—C15—O13	125.9 (2)	O8—N4—O7	124.0 (3)
C14—C15—C16	120.5 (3)	O8—N4—O6	120.6 (3)
O13—C15—C16	113.5 (2)	O7—N4—O6	115.4 (3)
C1—C2—C3	118.1 (3)	C6—C5—C4	119.2 (3)
C1—C2—C7	123.8 (2)	C6—C5—H5	120.4
C3—C2—C7	118.1 (3)	C4—C5—H5	120.4
C12—C11—C16	117.9 (2)	C19—C20—H20A	109.5
C12—C11—C10	118.1 (3)	C19—C20—H20B	109.5
C16—C11—C10	124.0 (2)	H20A—C20—H20B	109.5
N2—C7—C2	125.8 (3)	C19—C20—H20C	109.5
N2—C7—H7	117.1	H20A—C20—H20C	109.5
C2—C7—H7	117.1	H20B—C20—H20C	109.5
O2—C1—C6	116.6 (2)	N2—C8—C9	107.0 (2)
O2—C1—C2	123.9 (3)	N2—C8—H8A	110.3
C6—C1—C2	119.4 (2)	C9—C8—H8A	110.3
C5—C6—O12	125.5 (3)	N2—C8—H8B	110.3
C5—C6—C1	121.1 (3)	C9—C8—H8B	110.3
O12—C6—C1	113.3 (2)	H8A—C8—H8B	108.6

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C20—H20A···O6	0.96	2.44	3.121 (4)	128
C9—H9B···O4^i	0.97	2.40	3.278 (4)	151
C7—H7···O4^ii	0.93	2.38	3.293 (4)	167

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