Retracted: {μ-6,6′-Dieth­oxy-2,2′-[ethane-1,2-diylbis(nitrilo­methyl­idyne)]­diphenol­ato}trinitratopraseodymium(III)zinc(II)

In the title heteronuclear Zn^II–Pr^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′-praseodymium(III)zinc(II)), [PrZn(C₂₀H₂₂N₂O₄)(NO₃)₃], with the hexadentate Schiff base compartmental ligand N,N′-bis(3-ethoxysalicylidene)ethylenediamine (H₂2L), the Zn^II and Pr^III atoms are doubly bridged by two phenolate O atoms provided by the Schiff base ligand. The coordination of the Zn^II atom is approximately square planar, involving the two imine N atoms and the two phenolate O atoms. The Pr^III centre has a deca­coordination environment of O atoms, formed by the phenolate ligands, the two eth­oxy O atoms and two O atoms from each of the three nitrates. Some weak C—H...O and O...Zn [3.159 (4) Å] inter­actions generate a two-dimensional zigzag sheet.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.006 Å
• R factor = 0.027
• wR factor = 0.061
• Data-to-parameter ratio = 16.7

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT220_ALERT_2_C Large Non-Solvent    O     Ueq(max)/Ueq(min) ...       2.75 Ratio
PLAT230_ALERT_2_C Hirshfeld Test Diff for    O5     -   N3      ..       5.26 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for    O9     -   N4      ..       5.53 su
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Pr1    -   O5      ..       6.53 su
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Pr1    -   O9      ..       6.08 su
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Pr1    -   O11     ..       5.62 su
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         O8
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        O12
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        Pr1
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           28.23
           From the CIF: _reflns_number_total               6058
           Count of symmetry unique reflns         3531
           Completeness (_total/calc)            171.57%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured      2527
           Fraction of Friedel pairs measured     0.716
           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 Pr1         (3)       3.80
PLAT794_ALERT_5_G Check Predicted Bond Valency for Zn1         (2)       2.35

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
  10 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
  10 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

---

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; Knoer et al., 2005). As part of our investigations into the structure and applications of 3 d-4f hetorometallic Schiff base complexes (Sui et al., 2006), we report here the synthesis and X-ray crystal structure analysis of the title complex, (I), a new Zn^II–Pr^III complex with salen-type Schiff base N,N'-bis(3-ethoxysalicylidene) ethylenediamine(H₂L).

Complex (I) crystallizes in the space group P2₁2₁2₁, with zinc and praseodymium doubly bridged by two phenolate O atoms provided by a salen-type Schiff base ligand. The inner salen-type cavity is occupied by zinc(II), while praseodymium(III) is present in the open and larger portion of the dinucleating compartmental Schiff base ligand. The dihedral angles between the mean planes of Zn1/O1/O2 and Pr1/O1/O2 is 3.45 (15)° suggesting that the bridging moiety is almost planar; the deviation of atoms from the least squares Zn1/O1/O2/Pr1 plane being 0.0293 (3)Å for Zn, 0.0199 (3)Å for Pr, -0.0244 (4)Å for O1 and -0.0248 (4)Å for O2.

The praseodymium(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 from each of the three nitrates chelate to praseodymium to complete the decacoordination. The three kinds of Pr—O bond distances are significantly different, the shortest being the Pr—O(phenolate) and longest being the Pr—O(ethoxy) separations.

The coordination of zinc(II) is approximately square planar. The donor centers are alternatively above and below the mean N₂O₂ plane with an average deviation from the plane of 0.0901 (3) Å, while Zn1 is 0.0437 (3)Å below this square plane.

Adjacent molecules are held together by weak interactions (O10···Zn1 = 3.159 (5) Å, C7—H7···O7ⁱ = 3.276 (5), C9—H9A···O7ⁱⁱ = 3.266 (5) and C17—H17A···O8ⁱⁱⁱ = 3.528 (5); symmetry codes: (i) 1 - x, y - 1/2, 1/2 - z; (ii) x - 1, y, z; (iii) x - 1/2, 5/2 - y, z.) these link the molecules into a two-dimensional zigzag sheet (Fig. 2).

Related literature

For related literature, see: Baggio et al. (2000); Caravan et al. (1999); Edder et al. (2000); Knoer et al. (2005); Sui et al. (2006).

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 zinc(II) acetate dihydrate (0.188 g, 1 mmol) with H₂L(0.356 g, 1 mmol) in methanol solution (100 ml) under reflux for 3 h and then for another 3 h after the addition of praseodymium(III) nitrate hexahydrate (0.435 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 C₂₀H₂₂N₅O₁₃PrZn: C 32.17, H 2.97, N 9.38, Pr 18.87, Zn 8.76%; found: C 32.28, H 2.95, N 9.31, Pr 19.05, Zn 8.78%. IR (KBr, cm^-1): 1643 (C=N), 1385, 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: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: APEX2; software used to prepare material for publication: APEX2 and publCIF (Westrip, 2007).

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,\<i>N,N',O^1'}trinitrato-1κ⁶O,O'-πraseodymium(III)zinc(II))

Crystal data

[PrZn(C20H22N2O4)(NO3)3]	F(000) = 1480
Mr = 746.71	Dx = 1.960 Mg m^−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 19198 reflections
a = 8.6317 (7) Å	θ = 1.9–28.2°
b = 13.8782 (11) Å	µ = 2.93 mm^−1
c = 21.1267 (16) Å	T = 293 K
V = 2530.8 (3) Å^3	Block, yellow
Z = 4	0.21 × 0.15 × 0.13 mm

Data collection

Bruker APEXII area-detector diffractometer	6058 independent reflections
Radiation source: fine-focus sealed tube	4803 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.031
Detector resolution: 0 pixels mm^-1	θmax = 28.2°, θmin = 1.9°
φ and ω scans	h = −11→11
Absorption correction: multi-scan (SADABS; Bruker, 2004)	k = −18→17
Tmin = 0.605, Tmax = 0.683	l = −27→28
19198 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)] = 0.027	H-atom parameters constrained
wR(F^2) = 0.061	w = 1/[σ^2(Fo^2) + (0.0273P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.01	(Δ/σ)max = 0.002
6058 reflections	Δρmax = 0.50 e Å^−3
363 parameters	Δρmin = −0.62 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: 0.021 (12)

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
O7	0.9052 (4)	1.0762 (3)	0.27853 (15)	0.0806 (12)
O10	1.2389 (4)	1.0397 (3)	0.07303 (19)	0.0945 (13)
O13	0.5733 (4)	1.0012 (3)	−0.08812 (14)	0.0756 (9)
O1	0.5859 (3)	0.87492 (16)	0.13666 (12)	0.0373 (6)
Pr1	0.758724 (19)	0.999692 (14)	0.094892 (8)	0.03144 (5)
Zn1	0.43316 (5)	0.94378 (3)	0.18296 (2)	0.03984 (11)
O2	0.5377 (3)	1.05631 (17)	0.15394 (11)	0.0344 (6)
C16	0.4779 (4)	1.1447 (2)	0.15604 (17)	0.0324 (8)
N2	0.3000 (3)	1.0138 (2)	0.23919 (15)	0.0399 (8)
C2	0.7087 (4)	0.7432 (2)	0.08988 (17)	0.0328 (8)
N1	0.3204 (4)	0.8318 (2)	0.20905 (16)	0.0372 (8)
O3	0.8110 (3)	0.81322 (18)	0.06945 (13)	0.0377 (6)
C1	0.5866 (4)	0.7798 (2)	0.12626 (18)	0.0326 (8)
C15	0.5382 (4)	1.2125 (2)	0.11381 (18)	0.0333 (9)
O4	0.6539 (3)	1.17627 (17)	0.07518 (12)	0.0365 (6)
C10	0.2792 (4)	1.1050 (3)	0.23906 (18)	0.0389 (9)
H10	0.2104	1.1305	0.2686	0.047*
C11	0.3548 (5)	1.1715 (3)	0.19636 (19)	0.0381 (10)
C6	0.4752 (4)	0.7162 (3)	0.15047 (18)	0.0362 (9)
C8	0.1862 (5)	0.8551 (3)	0.2493 (2)	0.0450 (10)
H8A	0.1678	0.8036	0.2794	0.054*
H8B	0.0941	0.8630	0.2235	0.054*
C7	0.3493 (4)	0.7452 (3)	0.1915 (2)	0.0402 (10)
H7	0.2837	0.6971	0.2063	0.048*
C9	0.2226 (4)	0.9483 (3)	0.28391 (18)	0.0432 (9)
H9A	0.1278	0.9774	0.2995	0.052*
H9B	0.2897	0.9355	0.3198	0.052*
O11	0.7691 (3)	1.0125 (2)	−0.02391 (13)	0.0544 (7)
N5	0.6277 (4)	0.9941 (3)	−0.03462 (16)	0.0501 (8)
O6	0.8208 (4)	0.9677 (2)	0.21236 (15)	0.0540 (9)
O5	0.8639 (3)	1.1122 (2)	0.18006 (15)	0.0514 (7)
O8	1.0052 (4)	1.0817 (3)	0.04956 (16)	0.0674 (10)
O9	1.0450 (3)	0.9619 (2)	0.11152 (15)	0.0542 (8)
O12	0.5486 (3)	0.9684 (2)	0.01210 (14)	0.0600 (9)
N3	0.8645 (4)	1.0526 (3)	0.22519 (19)	0.0494 (9)
N4	1.1002 (4)	1.0277 (3)	0.07785 (18)	0.0536 (11)
C3	0.7170 (5)	0.6468 (3)	0.07493 (19)	0.0439 (10)
H3	0.7985	0.6234	0.0506	0.053*
C17	0.7260 (5)	1.2413 (3)	0.02942 (18)	0.0425 (9)
H17A	0.6464	1.2807	0.0099	0.051*
H17B	0.7748	1.2035	−0.0036	0.051*
C19	0.9463 (4)	0.7813 (3)	0.03462 (19)	0.0441 (10)
H19A	0.9888	0.8351	0.0110	0.053*
H19B	0.9158	0.7321	0.0045	0.053*
C4	0.6018 (5)	0.5849 (3)	0.0968 (2)	0.0499 (11)
H4	0.6048	0.5200	0.0859	0.060*
C5	0.4870 (5)	0.6179 (3)	0.1333 (2)	0.0448 (10)
H5	0.4125	0.5749	0.1478	0.054*
C20	1.0685 (5)	0.7415 (3)	0.0778 (2)	0.0585 (12)
H20A	1.0960	0.7892	0.1087	0.088*
H20B	1.1584	0.7244	0.0535	0.088*
H20C	1.0292	0.6852	0.0989	0.088*
C14	0.4813 (4)	1.3053 (3)	0.1114 (2)	0.0417 (10)
H14	0.5216	1.3497	0.0829	0.050*
C12	0.3023 (5)	1.2676 (3)	0.1951 (2)	0.0468 (11)
H12	0.2262	1.2876	0.2233	0.056*
C13	0.3623 (5)	1.3311 (3)	0.1527 (2)	0.0507 (11)
H13	0.3229	1.3935	0.1512	0.061*
C18	0.8445 (5)	1.3056 (3)	0.0590 (2)	0.0572 (13)
H18A	0.7941	1.3503	0.0870	0.086*
H18B	0.8984	1.3405	0.0265	0.086*
H18C	0.9170	1.2673	0.0826	0.086*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O7	0.086 (3)	0.112 (3)	0.0432 (18)	0.047 (2)	−0.0212 (19)	−0.025 (2)
O10	0.0346 (17)	0.142 (4)	0.107 (3)	−0.021 (2)	0.0064 (19)	0.004 (3)
O13	0.103 (2)	0.074 (2)	0.0496 (18)	−0.005 (2)	−0.0228 (18)	0.000 (2)
O1	0.0430 (15)	0.0200 (12)	0.0490 (16)	−0.0035 (11)	0.0155 (13)	0.0011 (11)
Pr1	0.03149 (9)	0.02595 (9)	0.03689 (9)	−0.00118 (11)	0.00386 (8)	0.00233 (10)
Zn1	0.0393 (2)	0.0319 (2)	0.0484 (2)	−0.00127 (19)	0.0103 (2)	0.0038 (2)
O2	0.0319 (13)	0.0252 (12)	0.0461 (14)	0.0024 (11)	0.0110 (12)	0.0032 (12)
C16	0.035 (2)	0.0256 (18)	0.037 (2)	0.0001 (14)	−0.0055 (17)	0.0018 (16)
N2	0.0380 (15)	0.046 (2)	0.0360 (17)	−0.0022 (14)	0.0057 (13)	0.0045 (16)
C2	0.0385 (19)	0.0280 (18)	0.0318 (19)	−0.0010 (13)	−0.0040 (17)	0.0032 (16)
N1	0.0367 (18)	0.0365 (19)	0.0385 (19)	−0.0051 (14)	0.0046 (15)	0.0092 (15)
O3	0.0353 (13)	0.0325 (14)	0.0455 (16)	0.0012 (11)	0.0085 (12)	−0.0013 (12)
C1	0.035 (2)	0.0272 (19)	0.035 (2)	−0.0006 (15)	−0.0058 (18)	0.0001 (16)
C15	0.032 (2)	0.0285 (19)	0.040 (2)	−0.0009 (14)	−0.0042 (17)	−0.0023 (16)
O4	0.0435 (15)	0.0250 (13)	0.0411 (16)	−0.0022 (11)	0.0063 (12)	0.0077 (11)
C10	0.037 (2)	0.040 (2)	0.040 (2)	0.0069 (17)	0.0043 (18)	0.0001 (18)
C11	0.036 (2)	0.037 (2)	0.042 (3)	0.0026 (16)	0.0013 (19)	0.0026 (18)
C6	0.044 (2)	0.0284 (19)	0.036 (2)	−0.0056 (15)	−0.0051 (18)	0.0051 (17)
C8	0.036 (2)	0.054 (3)	0.045 (2)	−0.0030 (18)	0.0102 (19)	0.012 (2)
C7	0.038 (2)	0.035 (2)	0.047 (3)	−0.0098 (16)	−0.003 (2)	0.0125 (19)
C9	0.042 (2)	0.044 (2)	0.043 (2)	0.0011 (18)	0.0110 (19)	0.0094 (19)
O11	0.0550 (17)	0.062 (2)	0.0461 (15)	−0.0113 (17)	0.0047 (13)	0.0002 (14)
N5	0.065 (2)	0.0392 (18)	0.046 (2)	0.001 (2)	−0.0037 (18)	−0.011 (2)
O6	0.059 (2)	0.056 (2)	0.0468 (18)	0.0084 (15)	0.0059 (15)	0.0152 (15)
O5	0.0562 (18)	0.0475 (17)	0.0505 (18)	0.0016 (14)	−0.0056 (16)	−0.0008 (16)
O8	0.0447 (18)	0.086 (3)	0.072 (2)	−0.0162 (16)	−0.0007 (17)	0.033 (2)
O9	0.0414 (16)	0.0446 (16)	0.077 (2)	0.0007 (13)	0.0054 (16)	0.0056 (15)
O12	0.0477 (16)	0.084 (3)	0.0482 (17)	−0.0121 (15)	0.0016 (15)	−0.0030 (16)
N3	0.0357 (19)	0.064 (3)	0.049 (2)	0.0208 (19)	−0.0028 (17)	−0.010 (2)
N4	0.038 (2)	0.069 (3)	0.054 (2)	−0.0086 (17)	0.0078 (18)	−0.0151 (19)
C3	0.058 (3)	0.031 (2)	0.044 (2)	0.0052 (18)	0.001 (2)	−0.0029 (17)
C17	0.054 (2)	0.0320 (19)	0.041 (2)	−0.0025 (17)	0.009 (2)	0.0081 (16)
C19	0.039 (2)	0.041 (2)	0.052 (3)	0.0045 (17)	0.008 (2)	−0.004 (2)
C4	0.065 (3)	0.028 (2)	0.057 (3)	−0.0013 (17)	−0.006 (2)	0.001 (2)
C5	0.057 (3)	0.024 (2)	0.053 (2)	−0.0102 (17)	−0.003 (2)	0.0066 (18)
C20	0.050 (3)	0.050 (3)	0.075 (3)	0.012 (2)	−0.004 (3)	−0.008 (2)
C14	0.043 (2)	0.035 (2)	0.048 (2)	−0.0004 (16)	−0.004 (2)	0.0052 (19)
C12	0.046 (2)	0.037 (2)	0.058 (3)	0.0104 (17)	0.007 (2)	−0.006 (2)
C13	0.059 (3)	0.027 (2)	0.066 (3)	0.0111 (18)	−0.002 (2)	0.001 (2)
C18	0.063 (3)	0.040 (3)	0.069 (3)	−0.011 (2)	0.020 (2)	−0.003 (2)

Geometric parameters (Å, º)

O7—N3	1.225 (5)	C6—C5	1.417 (5)
O10—N4	1.213 (4)	C6—C7	1.447 (6)
O13—N5	1.228 (4)	C8—C9	1.519 (6)
O1—C1	1.339 (4)	C8—H8A	0.9700
O1—Zn1	1.900 (2)	C8—H8B	0.9700
O1—Pr1	2.450 (2)	C7—H7	0.9300
Pr1—O2	2.411 (2)	C9—H9A	0.9700
Pr1—O11	2.518 (3)	C9—H9B	0.9700
Pr1—O5	2.549 (3)	O11—N5	1.267 (4)
Pr1—O9	2.550 (3)	N5—O12	1.252 (4)
Pr1—O12	2.557 (3)	O6—N3	1.266 (5)
Pr1—O6	2.578 (3)	O5—N3	1.262 (5)
Pr1—O8	2.596 (3)	O8—N4	1.262 (4)
Pr1—O4	2.645 (2)	O9—N4	1.252 (4)
Pr1—O3	2.681 (2)	C3—C4	1.394 (6)
Zn1—O2	1.905 (2)	C3—H3	0.9300
Zn1—N1	1.915 (3)	C17—C18	1.494 (6)
Zn1—N2	1.917 (3)	C17—H17A	0.9700
O2—C16	1.332 (4)	C17—H17B	0.9700
C16—C15	1.397 (5)	C19—C20	1.500 (6)
C16—C11	1.411 (5)	C19—H19A	0.9700
N2—C10	1.279 (5)	C19—H19B	0.9700
N2—C9	1.471 (5)	C4—C5	1.335 (5)
C2—C3	1.376 (5)	C4—H4	0.9300
C2—O3	1.383 (4)	C5—H5	0.9300
C2—C1	1.400 (5)	C20—H20A	0.9600
N1—C7	1.282 (5)	C20—H20B	0.9600
N1—C8	1.473 (5)	C20—H20C	0.9600
O3—C19	1.449 (4)	C14—C13	1.394 (6)
C1—C6	1.401 (5)	C14—H14	0.9300
C15—C14	1.379 (5)	C12—C13	1.360 (6)
C15—O4	1.384 (4)	C12—H12	0.9300
O4—C17	1.462 (4)	C13—H13	0.9300
C10—C11	1.446 (5)	C18—H18A	0.9600
C10—H10	0.9300	C18—H18B	0.9600
C11—C12	1.409 (5)	C18—H18C	0.9600
C1—O1—Zn1	125.7 (2)	N2—C10—C11	124.7 (4)
C1—O1—Pr1	129.5 (2)	N2—C10—H10	117.6
Zn1—O1—Pr1	104.62 (9)	C11—C10—H10	117.6
O2—Pr1—O1	64.04 (8)	C12—C11—C16	118.7 (4)
O2—Pr1—O11	121.38 (9)	C12—C11—C10	118.1 (4)
O1—Pr1—O11	115.51 (9)	C16—C11—C10	123.3 (3)
O2—Pr1—O5	73.57 (9)	C1—C6—C5	117.6 (4)
O1—Pr1—O5	113.29 (9)	C1—C6—C7	124.0 (3)
O11—Pr1—O5	130.36 (10)	C5—C6—C7	118.4 (3)
O2—Pr1—O9	139.68 (9)	N1—C8—C9	107.6 (3)
O1—Pr1—O9	113.26 (9)	N1—C8—H8A	110.2
O11—Pr1—O9	96.75 (10)	C9—C8—H8A	110.2
O5—Pr1—O9	71.56 (9)	N1—C8—H8B	110.2
O2—Pr1—O12	81.25 (9)	C9—C8—H8B	110.2
O1—Pr1—O12	72.21 (10)	H8A—C8—H8B	108.5
O11—Pr1—O12	49.85 (9)	N1—C7—C6	125.5 (4)
O5—Pr1—O12	147.08 (10)	N1—C7—H7	117.3
O9—Pr1—O12	138.30 (10)	C6—C7—H7	117.3
O2—Pr1—O6	73.90 (9)	N2—C9—C8	108.1 (3)
O1—Pr1—O6	70.01 (10)	N2—C9—H9A	110.1
O11—Pr1—O6	164.72 (10)	C8—C9—H9A	110.1
O5—Pr1—O6	49.60 (10)	N2—C9—H9B	110.1
O9—Pr1—O6	68.31 (10)	C8—C9—H9B	110.1
O12—Pr1—O6	140.99 (10)	H9A—C9—H9B	108.4
O2—Pr1—O8	134.14 (11)	N5—O11—Pr1	97.5 (2)
O1—Pr1—O8	160.35 (10)	O13—N5—O12	122.7 (4)
O11—Pr1—O8	64.67 (10)	O13—N5—O11	121.1 (4)
O5—Pr1—O8	72.54 (11)	O12—N5—O11	116.2 (3)
O9—Pr1—O8	49.23 (10)	N3—O6—Pr1	96.2 (2)
O12—Pr1—O8	113.79 (10)	N3—O5—Pr1	97.7 (2)
O6—Pr1—O8	105.08 (11)	N4—O8—Pr1	95.6 (2)
O2—Pr1—O4	60.58 (8)	N4—O9—Pr1	98.1 (2)
O1—Pr1—O4	120.21 (8)	N5—O12—Pr1	96.0 (2)
O11—Pr1—O4	77.86 (9)	O7—N3—O5	121.4 (4)
O5—Pr1—O4	70.47 (9)	O7—N3—O6	122.1 (5)
O9—Pr1—O4	122.93 (8)	O5—N3—O6	116.5 (4)
O12—Pr1—O4	78.87 (9)	O10—N4—O9	121.6 (4)
O6—Pr1—O4	112.47 (9)	O10—N4—O8	121.3 (4)
O8—Pr1—O4	79.40 (10)	O9—N4—O8	117.1 (3)
O2—Pr1—O3	123.47 (8)	C2—C3—C4	119.1 (4)
O1—Pr1—O3	59.51 (7)	C2—C3—H3	120.5
O11—Pr1—O3	82.10 (9)	C4—C3—H3	120.5
O5—Pr1—O3	132.26 (9)	O4—C17—C18	112.5 (3)
O9—Pr1—O3	70.49 (8)	O4—C17—H17A	109.1
O12—Pr1—O3	79.54 (9)	C18—C17—H17A	109.1
O6—Pr1—O3	89.53 (9)	O4—C17—H17B	109.1
O8—Pr1—O3	102.19 (10)	C18—C17—H17B	109.1
O4—Pr1—O3	156.94 (9)	H17A—C17—H17B	107.8
O1—Zn1—O2	85.30 (10)	O3—C19—C20	111.7 (3)
O1—Zn1—N1	95.31 (12)	O3—C19—H19A	109.3
O2—Zn1—N1	177.18 (13)	C20—C19—H19A	109.3
O1—Zn1—N2	171.90 (13)	O3—C19—H19B	109.3
O2—Zn1—N2	93.89 (12)	C20—C19—H19B	109.3
N1—Zn1—N2	85.89 (15)	H19A—C19—H19B	107.9
C16—O2—Zn1	124.1 (2)	C5—C4—C3	120.6 (4)
C16—O2—Pr1	128.6 (2)	C5—C4—H4	119.7
Zn1—O2—Pr1	105.91 (10)	C3—C4—H4	119.7
O2—C16—C15	117.0 (3)	C4—C5—C6	122.1 (4)
O2—C16—C11	123.6 (3)	C4—C5—H5	118.9
C15—C16—C11	119.3 (3)	C6—C5—H5	118.9
C10—N2—C9	123.3 (3)	C19—C20—H20A	109.5
C10—N2—Zn1	125.8 (3)	C19—C20—H20B	109.5
C9—N2—Zn1	110.9 (3)	H20A—C20—H20B	109.5
C3—C2—O3	125.3 (3)	C19—C20—H20C	109.5
C3—C2—C1	121.2 (3)	H20A—C20—H20C	109.5
O3—C2—C1	113.4 (3)	H20B—C20—H20C	109.5
C7—N1—C8	121.7 (3)	C15—C14—C13	118.7 (4)
C7—N1—Zn1	125.4 (3)	C15—C14—H14	120.7
C8—N1—Zn1	112.8 (3)	C13—C14—H14	120.7
C2—O3—C19	117.3 (3)	C13—C12—C11	120.3 (4)
C2—O3—Pr1	120.5 (2)	C13—C12—H12	119.9
C19—O3—Pr1	122.2 (2)	C11—C12—H12	119.9
O1—C1—C2	116.8 (3)	C12—C13—C14	121.7 (4)
O1—C1—C6	123.9 (3)	C12—C13—H13	119.2
C2—C1—C6	119.3 (3)	C14—C13—H13	119.2
C14—C15—O4	125.1 (3)	C17—C18—H18A	109.5
C14—C15—C16	121.3 (3)	C17—C18—H18B	109.5
O4—C15—C16	113.7 (3)	H18A—C18—H18B	109.5
C15—O4—C17	118.2 (3)	C17—C18—H18C	109.5
C15—O4—Pr1	119.4 (2)	H18A—C18—H18C	109.5
C17—O4—Pr1	122.0 (2)	H18B—C18—H18C	109.5

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C20—H20A···O9	0.96	2.44	3.148 (5)	131
C17—H17A···O8^i	0.97	2.59	3.528 (5)	163
C9—H9A···O7^ii	0.97	2.40	3.266 (5)	148
C7—H7···O7^iii	0.93	2.36	3.276 (5)	168

Symmetry codes: (i) x−1/2, −y+5/2, −z; (ii) x−1, y, z; (iii) −x+1, y−1/2, −z+1/2.