Retracted: {6,6′-Dimeth­oxy-2,2′-[ethane-1,2-diylbis(nitrilo­methyl­idyne)]­diphenolato}­methanol-μ-nitrato-dinitratopraseodymium(III)zinc(II)

In the title heteronuclear Zn^II–Pr^III complex (systematic name: {6,6′-dimeth­oxy-2,2′-[ethane-1,2-diylbis(nitrilo­methylidyne)]diphenolato-1κ⁴O¹,O^1′,O⁶,O^6′:2κ⁴O¹,N,N′,O^1′}(methanol-1κO)-μ-nitrato-1:2κ²O:O′-dinitrato-1κ⁴O,O′-praseodymium(III)zinc(II)), [PrZn(C₁₈H₁₈N₂O₄)(NO₃)₃(CH₄O)], with the hexa­dentate Schiff base compartmental ligand N,N′-bis­(3-methoxy­salicyl­idene)ethyl­enediamine (H₂L), the Pr and Zn atoms are triply bridged by two phenolate O atoms provided by the Schiff base ligand and one nitrate. The five-coordinate Zn atom is in a square-pyramidal geometry, with the donor centers of two imine N atoms, two phenolate O atoms and one of the bridging nitrate O atoms. The Pr^III center has a tenfold coordination environment of O atoms, involving the phenolate O atoms, two meth­oxy O atoms, one methanol O atom, and two O atoms from two nitrates and one from the bridging nitrate. Strong inter­molecular O—H...O and some weak C—H...O inter­actions generate a two-dimensional layer structure.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.025
• wR factor = 0.076
• Data-to-parameter ratio = 17.4

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low .......       0.97
PLAT062_ALERT_4_C Rescale T(min) & T(max) by .....................       0.97
PLAT220_ALERT_2_C Large Non-Solvent    O     Ueq(max)/Ueq(min) ...       3.19 Ratio
PLAT230_ALERT_2_C Hirshfeld Test Diff for    O12    -   N5      ..       6.09 su
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Pr1    -   O3      ..       5.97 su
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Pr1    -   O8      ..       6.75 su
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Pr1    -   O9      ..       5.40 su
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Pr1    -   O11     ..       5.28 su
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         N3
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         N5

Alert level G
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)       3.34
PLAT794_ALERT_5_G Check Predicted Bond Valency for Zn1         (2)       2.12
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......          5

   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
   8 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 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; Sui et al., 2007), 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-methoxysalicylidene) ethylenediamine (H₂L).

Complex (I) crystallizes in the space group P2₁/n, with zinc and praseodymium triply bridged by two phenolate O atoms provided by a salen-type Schiff base ligand and one nitrate. 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 Pr^III center has a decacoordination environment of O atoms, involving the phenolate O atoms, two methoxy O atoms, one methanol O atom, two O atoms from two nitrates and one from the bridging nitrate. The five kinds of Pr—O bond distances are significantly different, the longest being the Pr—O(methoxy) separations and the shortest being the Pr—O(phenolate) and Pr—O11(bridging nitrate).

The Zn^II is in a square-pyramidal geometry and is five-coordinated by two imine N atoms, two phenolate O atoms and one of the bridging nitrate O atoms. The Zn atom is 0.5835 (3)Å above the mean N₂O₂ plane with an average deviation from the plane of 0.0959 (4) Å, which construct the bottom of square-pyramid. The Zn—O13(bridging nitrate) separation is 2.005 (2)Å and the angles of this Zn—O vector with the Zn—N or Zn—O bonds lie between 103.2 (3)° and 115.6 (3)°, which suggesting that the Zn^II is in a slightly distorted square-pyramidal conformation.

Adjacent molecules are held together by strong interactions [O14—H14A··· O13ⁱ = 2.689 (3); symmetry codes: (i) 3/2 - x, y - 1/2, 1/2 - z] and weak interactions [C7—H7···O8ⁱⁱ = 3.391 (4) and C5—H5···O3ⁱⁱ = 3.429 (4); symmetry codes:(ii) 1/2 + x, 1/2 - y, 1/2 + z]. These link the molecules into a two-dimensional layer structure (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, 2007).

S2. Experimental

H₂L was prepared by the 2:1 condensation of 3-methoxysalicylaldehyde and ethylenediamine in methanol. Complex (I) was obtained by the treatment of zinc(II) acetate dihydrate (0.188 g, 1 mmol) with H₂L (0.328 g, 1 mmol) in methanol solution (80 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 C₁₉H₂₂N₅O₁₄PrZn: C 30.40, H 2.95, N 9.33, Pr 18.77, Zn 8.71%; found: C 30.15, H 2.92, N 9.38, Pr 18.59, Zn 8.66%. IR (KBr, cm^-1): 1640(C?N), 1386,1490(nitrate).

S3. Refinement

The H bound O atom was found from a difference Fourier map and refined freely. The H atoms were positioned geometrically and treated as riding on their parent atoms, with C—H distances of 0.93 (aromatic), 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. The methyl group of methanol was constrainted as idealized no-rotating CH₃ group.

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.
	Fig. 2. The packing diagram of (I), viewed along the c axis; hydrogen bonds are shown as dashed lines.

{6,6'-dimethoxy-2,2'-[ethane-1,2-diylbis(nitrilomethylidyne)]diphenolato-\1κ⁴O¹,O^1',O⁶,O^6':2κ⁴O¹,N,\<i>N',O^1')(methanol-1κO)-µ-nitrato-1:2κ²O:O'-\ dinitrato-1κ⁴O,O'-praseodymium(III)zinc(II)

Crystal data

[PrZn(C18H18N2O4)(NO3)3(CH4O)]	F(000) = 1488
Mr = 750.70	Dx = 1.878 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 6083 reflections
a = 9.6011 (4) Å	θ = 1.8–28.3°
b = 13.8046 (5) Å	µ = 2.79 mm^−1
c = 20.0375 (7) Å	T = 293 K
β = 91.629 (1)°	Block, yellow
V = 2654.68 (17) Å^3	0.30 × 0.22 × 0.15 mm
Z = 4

Data collection

Bruker APEXII area-detector diffractometer	6372 independent reflections
Radiation source: fine-focus sealed tube	5465 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.020
φ and ω scans	θmax = 28.3°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −12→12
Tmin = 0.488, Tmax = 0.679	k = −18→18
19675 measured reflections	l = −26→26

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)] = 0.025	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.076	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	w = 1/[σ^2(Fo^2) + (0.0512P)^2 + 0.717P] where P = (Fo^2 + 2Fc^2)/3
6372 reflections	(Δ/σ)max = 0.001
367 parameters	Δρmax = 0.74 e Å^−3
5 restraints	Δρmin = −0.70 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
Pr1	0.721733 (14)	0.278496 (10)	0.113900 (6)	0.02796 (6)
Zn1	0.68898 (3)	0.37172 (2)	0.273215 (15)	0.03249 (8)
O1	0.82378 (19)	0.28226 (13)	0.22807 (9)	0.0329 (4)
O2	0.55769 (18)	0.32507 (14)	0.19980 (9)	0.0352 (4)
O3	0.7364 (2)	0.36395 (17)	0.00049 (10)	0.0464 (5)
O7	0.4591 (2)	0.35441 (16)	0.08039 (10)	0.0438 (5)
O6	0.9691 (2)	0.18028 (15)	0.14816 (10)	0.0385 (4)
C1	0.9349 (3)	0.23950 (19)	0.25573 (13)	0.0302 (5)
O4	0.9351 (2)	0.33213 (17)	0.04734 (11)	0.0463 (5)
N1	0.7947 (3)	0.35333 (18)	0.36133 (12)	0.0419 (6)
C11	0.3434 (3)	0.3729 (2)	0.25103 (16)	0.0411 (7)
N2	0.5233 (3)	0.36915 (18)	0.33710 (12)	0.0443 (6)
C16	0.4263 (3)	0.35504 (18)	0.19526 (15)	0.0332 (6)
C6	0.9764 (3)	0.2473 (2)	0.32366 (14)	0.0387 (6)
C12	0.2019 (3)	0.3977 (2)	0.2390 (2)	0.0540 (9)
H12	0.1453	0.4076	0.2753	0.065*
N3	0.8672 (3)	0.3668 (2)	−0.00158 (14)	0.0494 (6)
C2	1.0167 (3)	0.1826 (2)	0.21401 (14)	0.0354 (6)
C15	0.3670 (3)	0.3692 (2)	0.13133 (16)	0.0385 (6)
C14	0.2281 (3)	0.3947 (2)	0.12128 (19)	0.0496 (8)
H14	0.1906	0.4031	0.0784	0.060*
C5	1.0960 (3)	0.1962 (3)	0.34674 (17)	0.0506 (8)
H5	1.1232	0.2003	0.3916	0.061*
C3	1.1330 (3)	0.1341 (2)	0.23812 (18)	0.0473 (7)
H3	1.1853	0.0965	0.2096	0.057*
C7	0.9014 (3)	0.3013 (2)	0.37299 (14)	0.0426 (7)
H7	0.9343	0.2975	0.4170	0.051*
C9	0.5654 (4)	0.3618 (3)	0.40742 (15)	0.0550 (9)
H9A	0.5585	0.2951	0.4221	0.066*
H9B	0.5043	0.4009	0.4342	0.066*
C10	0.3950 (3)	0.3688 (2)	0.31916 (17)	0.0469 (8)
H10	0.3298	0.3656	0.3525	0.056*
O5	0.9252 (4)	0.4006 (3)	−0.04924 (16)	0.1051 (13)
C8	0.7151 (4)	0.3971 (3)	0.41655 (15)	0.0543 (9)
H8A	0.7188	0.4672	0.4143	0.065*
H8B	0.7537	0.3766	0.4595	0.065*
C13	0.1462 (3)	0.4075 (2)	0.1768 (2)	0.0565 (9)
H13	0.0523	0.4229	0.1709	0.068*
O14	0.6428 (2)	0.11820 (14)	0.16097 (11)	0.0407 (5)
O8	0.5706 (2)	0.18210 (16)	0.02343 (10)	0.0444 (5)
O11	0.7639 (2)	0.45080 (15)	0.13810 (10)	0.0462 (5)
O9	0.7876 (2)	0.14450 (16)	0.02637 (11)	0.0469 (5)
N4	0.6692 (3)	0.13211 (18)	0.00000 (12)	0.0433 (6)
C18	1.0643 (4)	0.1419 (3)	0.10131 (17)	0.0534 (8)
H18A	1.1529	0.1736	0.1070	0.080*
H18B	1.0284	0.1527	0.0567	0.080*
H18C	1.0756	0.0736	0.1088	0.080*
C17	0.4082 (4)	0.3800 (3)	0.01438 (18)	0.0603 (9)
H17A	0.3363	0.3355	0.0004	0.090*
H17B	0.4833	0.3770	−0.0162	0.090*
H17C	0.3711	0.4446	0.0149	0.090*
C4	1.1719 (4)	0.1414 (3)	0.30528 (19)	0.0563 (9)
H4	1.2502	0.1086	0.3217	0.068*
O13	0.7476 (2)	0.50348 (14)	0.24262 (10)	0.0397 (4)
N5	0.7784 (3)	0.51487 (19)	0.18159 (13)	0.0450 (6)
O10	0.6494 (3)	0.0758 (2)	−0.04565 (13)	0.0748 (8)
O12	0.8398 (4)	0.6104 (2)	0.16159 (19)	0.0994 (11)
C19	0.5002 (4)	0.0896 (3)	0.1617 (2)	0.0641 (10)
H19A	0.4715	0.0842	0.2071	0.096*
H19B	0.4891	0.0281	0.1398	0.096*
H19C	0.4438	0.1372	0.1388	0.096*
H14A	0.695 (3)	0.085 (2)	0.1890 (14)	0.049 (10)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Pr1	0.03016 (9)	0.03434 (9)	0.01918 (8)	0.00085 (5)	−0.00257 (6)	−0.00135 (5)
Zn1	0.03917 (17)	0.03690 (16)	0.02147 (15)	−0.00117 (12)	0.00195 (13)	−0.00117 (12)
O1	0.0310 (9)	0.0455 (10)	0.0218 (9)	0.0064 (7)	−0.0045 (8)	−0.0012 (7)
O2	0.0279 (9)	0.0467 (11)	0.0309 (10)	0.0051 (8)	0.0010 (8)	−0.0056 (8)
O3	0.0436 (12)	0.0658 (14)	0.0295 (10)	0.0013 (10)	−0.0048 (9)	0.0085 (10)
O7	0.0347 (10)	0.0606 (13)	0.0355 (11)	0.0099 (9)	−0.0079 (9)	−0.0066 (10)
O6	0.0360 (10)	0.0503 (11)	0.0289 (10)	0.0089 (9)	−0.0044 (8)	−0.0049 (8)
C1	0.0300 (12)	0.0358 (13)	0.0243 (12)	−0.0039 (10)	−0.0071 (10)	0.0061 (10)
O4	0.0344 (10)	0.0598 (13)	0.0446 (12)	−0.0017 (9)	0.0003 (9)	0.0093 (11)
N1	0.0589 (16)	0.0453 (13)	0.0214 (11)	−0.0059 (11)	−0.0011 (11)	−0.0020 (10)
C11	0.0375 (15)	0.0331 (13)	0.0535 (18)	−0.0023 (11)	0.0161 (14)	−0.0038 (12)
N2	0.0562 (16)	0.0452 (13)	0.0324 (12)	0.0001 (11)	0.0155 (12)	0.0006 (10)
C16	0.0261 (12)	0.0308 (12)	0.0430 (15)	−0.0012 (9)	0.0031 (11)	−0.0057 (11)
C6	0.0377 (15)	0.0491 (15)	0.0288 (14)	−0.0065 (12)	−0.0105 (12)	0.0100 (12)
C12	0.0365 (16)	0.0433 (16)	0.083 (3)	−0.0003 (13)	0.0257 (18)	−0.0069 (17)
N3	0.0529 (16)	0.0583 (16)	0.0375 (14)	−0.0004 (13)	0.0097 (13)	0.0086 (12)
C2	0.0329 (13)	0.0372 (13)	0.0356 (14)	−0.0009 (11)	−0.0058 (11)	0.0040 (11)
C15	0.0280 (13)	0.0370 (14)	0.0502 (18)	0.0007 (10)	−0.0025 (12)	−0.0085 (12)
C14	0.0306 (15)	0.0485 (17)	0.069 (2)	0.0031 (12)	−0.0097 (15)	−0.0067 (15)
C5	0.0479 (18)	0.065 (2)	0.0376 (17)	−0.0001 (16)	−0.0171 (15)	0.0134 (16)
C3	0.0382 (15)	0.0488 (17)	0.054 (2)	0.0104 (13)	−0.0084 (14)	0.0078 (15)
C7	0.0538 (18)	0.0525 (16)	0.0208 (13)	−0.0126 (14)	−0.0123 (13)	0.0044 (12)
C9	0.078 (2)	0.0580 (19)	0.0297 (15)	0.0055 (17)	0.0211 (16)	0.0010 (14)
C10	0.0505 (18)	0.0418 (15)	0.0497 (18)	−0.0006 (13)	0.0237 (15)	−0.0034 (13)
O5	0.088 (2)	0.159 (3)	0.070 (2)	0.005 (2)	0.0345 (18)	0.060 (2)
C8	0.089 (3)	0.0498 (17)	0.0248 (14)	0.0031 (17)	0.0052 (16)	−0.0079 (13)
C13	0.0278 (14)	0.0485 (18)	0.093 (3)	0.0055 (12)	0.0044 (17)	−0.0041 (18)
O14	0.0426 (11)	0.0401 (10)	0.0391 (11)	−0.0037 (9)	−0.0017 (9)	0.0098 (9)
O8	0.0465 (12)	0.0521 (12)	0.0339 (11)	0.0026 (10)	−0.0125 (9)	−0.0035 (10)
O11	0.0671 (14)	0.0404 (10)	0.0311 (9)	−0.0039 (10)	0.0038 (10)	−0.0018 (7)
O9	0.0455 (12)	0.0539 (12)	0.0410 (12)	0.0031 (9)	−0.0027 (10)	−0.0154 (9)
N4	0.0611 (16)	0.0402 (13)	0.0282 (12)	−0.0015 (11)	−0.0069 (12)	−0.0022 (10)
C18	0.0475 (18)	0.069 (2)	0.0438 (18)	0.0174 (16)	0.0048 (15)	−0.0088 (16)
C17	0.057 (2)	0.080 (3)	0.0426 (18)	0.0153 (18)	−0.0166 (16)	−0.0036 (18)
C4	0.0482 (18)	0.067 (2)	0.052 (2)	0.0128 (16)	−0.0194 (16)	0.0164 (17)
O13	0.0536 (12)	0.0339 (9)	0.0319 (8)	−0.0046 (8)	0.0031 (9)	−0.0028 (7)
N5	0.0571 (15)	0.0421 (12)	0.0360 (10)	0.0030 (11)	0.0036 (12)	−0.0023 (9)
O10	0.100 (2)	0.0690 (17)	0.0543 (16)	0.0012 (15)	−0.0202 (15)	−0.0343 (14)
O12	0.135 (3)	0.0654 (18)	0.099 (3)	−0.0109 (19)	0.030 (2)	0.0017 (18)
C19	0.051 (2)	0.073 (2)	0.069 (2)	−0.0208 (18)	−0.0020 (18)	0.015 (2)

Geometric parameters (Å, º)

Pr1—O1	2.4634 (19)	C12—H12	0.9300
Pr1—O2	2.4517 (17)	N3—O5	1.212 (4)
Pr1—O3	2.568 (2)	C2—C3	1.378 (4)
Pr1—O4	2.584 (2)	C15—C14	1.389 (4)
Pr1—O6	2.8027 (19)	C14—C13	1.391 (5)
Pr1—O7	2.7945 (19)	C14—H14	0.9300
Pr1—O8	2.648 (2)	C5—C4	1.351 (5)
Pr1—O9	2.638 (2)	C5—H5	0.9300
Pr1—O11	2.459 (2)	C3—C4	1.390 (5)
Pr1—O14	2.5302 (19)	C3—H3	0.9300
Zn1—O1	2.0212 (18)	C7—H7	0.9300
Zn1—O2	2.0155 (19)	C9—C8	1.523 (5)
Zn1—O13	2.005 (2)	C9—H9A	0.9700
Zn1—N1	2.027 (3)	C9—H9B	0.9700
Zn1—N2	2.070 (2)	C10—H10	0.9300
O1—C1	1.327 (3)	C8—H8A	0.9700
O2—C16	1.328 (3)	C8—H8B	0.9700
O3—N3	1.259 (3)	C13—H13	0.9300
O7—C15	1.385 (3)	O14—C19	1.425 (4)
O7—C17	1.441 (4)	O14—H14A	0.875 (18)
O6—C2	1.384 (3)	O8—N4	1.272 (3)
O6—C18	1.431 (4)	O11—N5	1.247 (3)
C1—C2	1.404 (4)	O9—N4	1.252 (3)
C1—C6	1.411 (4)	N4—O10	1.211 (3)
O4—N3	1.256 (3)	C18—H18A	0.9600
N1—C7	1.268 (4)	C18—H18B	0.9600
N1—C8	1.490 (4)	C18—H18C	0.9600
C11—C16	1.412 (4)	C17—H17A	0.9600
C11—C12	1.416 (4)	C17—H17B	0.9600
C11—C10	1.440 (5)	C17—H17C	0.9600
N2—C10	1.273 (4)	C4—H4	0.9300
N2—C9	1.458 (4)	O13—N5	1.276 (3)
C16—C15	1.401 (4)	N5—O12	1.503 (4)
C6—C5	1.415 (4)	C19—H19A	0.9600
C6—C7	1.446 (5)	C19—H19B	0.9600
C12—C13	1.350 (5)	C19—H19C	0.9600
O2—Pr1—O11	73.34 (7)	O2—C16—C11	123.8 (3)
O2—Pr1—O1	65.73 (6)	C15—C16—C11	118.4 (3)
O11—Pr1—O1	74.79 (7)	C1—C6—C5	118.8 (3)
O2—Pr1—O14	76.25 (7)	C1—C6—C7	124.5 (3)
O11—Pr1—O14	145.28 (7)	C5—C6—C7	116.7 (3)
O1—Pr1—O14	77.75 (7)	C13—C12—C11	122.3 (3)
O2—Pr1—O3	123.59 (7)	C13—C12—H12	118.9
O11—Pr1—O3	73.58 (7)	C11—C12—H12	118.9
O1—Pr1—O3	141.43 (7)	O5—N3—O4	121.5 (3)
O14—Pr1—O3	139.13 (7)	O5—N3—O3	121.3 (3)
O2—Pr1—O4	145.25 (7)	O4—N3—O3	117.3 (2)
O11—Pr1—O4	72.31 (7)	C3—C2—O6	124.4 (3)
O1—Pr1—O4	99.97 (7)	C3—C2—C1	121.6 (3)
O14—Pr1—O4	133.89 (7)	O6—C2—C1	113.9 (2)
O3—Pr1—O4	49.27 (7)	O7—C15—C14	124.2 (3)
O2—Pr1—O9	145.23 (7)	O7—C15—C16	113.7 (2)
O11—Pr1—O9	140.19 (7)	C14—C15—C16	122.1 (3)
O1—Pr1—O9	122.39 (6)	C15—C14—C13	118.6 (3)
O14—Pr1—O9	73.42 (7)	C15—C14—H14	120.7
O3—Pr1—O9	73.35 (7)	C13—C14—H14	120.7
O4—Pr1—O9	69.47 (7)	C4—C5—C6	121.6 (3)
O2—Pr1—O8	105.18 (6)	C4—C5—H5	119.2
O11—Pr1—O8	134.83 (7)	C6—C5—H5	119.2
O1—Pr1—O8	147.35 (7)	C2—C3—C4	119.8 (3)
O14—Pr1—O8	69.60 (7)	C2—C3—H3	120.1
O3—Pr1—O8	70.59 (7)	C4—C3—H3	120.1
O4—Pr1—O8	102.57 (7)	N1—C7—C6	125.6 (3)
O9—Pr1—O8	47.90 (7)	N1—C7—H7	117.2
O2—Pr1—O7	58.48 (6)	C6—C7—H7	117.2
O11—Pr1—O7	80.04 (7)	N2—C9—C8	109.2 (2)
O1—Pr1—O7	123.20 (6)	N2—C9—H9A	109.8
O14—Pr1—O7	98.03 (7)	C8—C9—H9A	109.8
O3—Pr1—O7	71.74 (7)	N2—C9—H9B	109.8
O4—Pr1—O7	119.44 (7)	C8—C9—H9B	109.8
O9—Pr1—O7	109.56 (6)	H9A—C9—H9B	108.3
O8—Pr1—O7	63.31 (6)	N2—C10—C11	124.8 (3)
O2—Pr1—O6	120.77 (6)	N2—C10—H10	117.6
O11—Pr1—O6	106.62 (7)	C11—C10—H10	117.6
O1—Pr1—O6	58.06 (6)	N1—C8—C9	106.4 (3)
O14—Pr1—O6	75.31 (6)	N1—C8—H8A	110.4
O3—Pr1—O6	111.82 (6)	C9—C8—H8A	110.4
O4—Pr1—O6	65.58 (6)	N1—C8—H8B	110.4
O9—Pr1—O6	66.82 (6)	C9—C8—H8B	110.4
O8—Pr1—O6	111.63 (6)	H8A—C8—H8B	108.6
O7—Pr1—O6	173.01 (6)	C12—C13—C14	120.5 (3)
O13—Zn1—O2	104.00 (8)	C12—C13—H13	119.7
O13—Zn1—O1	103.21 (8)	C14—C13—H13	119.7
O2—Zn1—O1	82.72 (7)	C19—O14—Pr1	123.0 (2)
O13—Zn1—N1	104.00 (9)	C19—O14—H14A	113 (2)
O2—Zn1—N1	151.99 (9)	Pr1—O14—H14A	122 (2)
O1—Zn1—N1	90.13 (9)	N4—O8—Pr1	97.25 (16)
O13—Zn1—N2	115.59 (9)	N5—O11—Pr1	147.00 (18)
O2—Zn1—N2	88.29 (9)	N4—O9—Pr1	98.31 (16)
O1—Zn1—N2	141.20 (9)	O10—N4—O9	121.8 (3)
N1—Zn1—N2	80.43 (11)	O10—N4—O8	121.7 (3)
C1—O1—Zn1	127.04 (17)	O9—N4—O8	116.5 (2)
C1—O1—Pr1	132.26 (16)	O6—C18—H18A	109.5
Zn1—O1—Pr1	100.70 (7)	O6—C18—H18B	109.5
C16—O2—Zn1	121.57 (16)	H18A—C18—H18B	109.5
C16—O2—Pr1	131.41 (17)	O6—C18—H18C	109.5
Zn1—O2—Pr1	101.26 (7)	H18A—C18—H18C	109.5
N3—O3—Pr1	97.09 (17)	H18B—C18—H18C	109.5
C15—O7—C17	115.7 (2)	O7—C17—H17A	109.5
C15—O7—Pr1	117.96 (17)	O7—C17—H17B	109.5
C17—O7—Pr1	126.35 (18)	H17A—C17—H17B	109.5
C2—O6—C18	115.7 (2)	O7—C17—H17C	109.5
C2—O6—Pr1	118.49 (15)	H17A—C17—H17C	109.5
C18—O6—Pr1	124.85 (18)	H17B—C17—H17C	109.5
O1—C1—C2	117.2 (2)	C5—C4—C3	120.1 (3)
O1—C1—C6	124.8 (3)	C5—C4—H4	120.0
C2—C1—C6	118.0 (2)	C3—C4—H4	120.0
N3—O4—Pr1	96.37 (16)	N5—O13—Zn1	118.65 (17)
C7—N1—C8	121.5 (3)	O11—N5—O13	123.9 (2)
C7—N1—Zn1	127.8 (2)	O11—N5—O12	118.2 (2)
C8—N1—Zn1	110.0 (2)	O13—N5—O12	117.8 (3)
C16—C11—C12	117.9 (3)	O14—C19—H19A	109.5
C16—C11—C10	123.9 (3)	O14—C19—H19B	109.5
C12—C11—C10	118.2 (3)	H19A—C19—H19B	109.5
C10—N2—C9	120.8 (3)	O14—C19—H19C	109.5
C10—N2—Zn1	125.4 (2)	H19A—C19—H19C	109.5
C9—N2—Zn1	113.7 (2)	H19B—C19—H19C	109.5
O2—C16—C15	117.8 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C18—H18B···O9	0.96	2.38	3.015 (4)	124
C17—H17B···O3	0.96	2.45	3.178 (4)	133
C5—H5···O3^i	0.93	2.57	3.429 (4)	154
C7—H7···O8^i	0.93	2.49	3.391 (4)	165
O14—H14A···O13^ii	0.88 (2)	1.84 (2)	2.689 (3)	162 (3)

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