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Reaction of [Zn(hfac)2]·2H2O with L1, where hfac and L1 are hexa­fluoro­acetyl­acetonate and 2,6-bis­[1-(4-tert-butyl­phenyl­imino)­ethyl]­pyridine, respectively, results in the formation of [Zn(L1)2][Zn(hfac)3]2, i.e. [Zn(C29H35N3)2][Zn(C5HF6O2)3]2·0.5C4H10O. In the cation, the two L1 ligands act as mer-terdentate ligands. Reaction of [Zn(hfac)2]·2H2O with 2,2':6',2''-ter­pyridine (terpy) results in the formation of [Zn(terpy)2](hfac)2.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536801015458/cv6059sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536801015458/cv6059Isup2.hkl
Contains datablock I

CCDC reference: 175983

Key indicators

  • Single-crystal X-ray study
  • T = 150 K
  • Mean [sigma](C-C) = 0.064 Å
  • R factor = 0.061
  • wR factor = 0.129
  • Data-to-parameter ratio = 10.4

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


Red Alert Alert Level A:
REFLT_03 From the CIF: _diffrn_reflns_theta_max 25.14 From the CIF: _reflns_number_total 14012 TEST2: Reflns within _diffrn_reflns_theta_max Count of symmetry unique reflns 17977 Completeness (_total/calc) 77.94% Alert A: < 85% complete (theta max?) SHFSU_01 Alert A The absolute value of parameter shift to su ratio > 0.20 Absolute value of the parameter shift to su ratio given 1.002 Additional refinement cycles may be required. PLAT_213 Alert A Atom C69 has ADP max/min Ratio ........... 16.60 PLAT_213 Alert A Atom C72 has ADP max/min Ratio ........... 9.40 PLAT_369 Alert A Long C(sp2)-C(sp2) Bond C(71) - C(72) = 1.66 Ang.
Amber Alert Alert Level B:
PLAT_213 Alert B Atom F34 has ADP max/min Ratio ........... 4.50 PLAT_213 Alert B Atom F5 has ADP max/min Ratio ........... 4.60
Yellow Alert Alert Level C:
GOODF_01 Alert C The least squares goodness of fit parameter lies outside the range 0.80 <> 2.00 Goodness of fit given = 0.758 PLAT_213 Alert C Atom C26 has ADP max/min Ratio ........... 3.50 PLAT_213 Alert C Atom C57 has ADP max/min Ratio ........... 3.60 PLAT_213 Alert C Atom C87 has ADP max/min Ratio ........... 3.20 PLAT_213 Alert C Atom F3 has ADP max/min Ratio ........... 3.20 PLAT_213 Alert C Atom F6 has ADP max/min Ratio ........... 3.70 PLAT_213 Alert C Atom F12 has ADP max/min Ratio ........... 3.20 PLAT_213 Alert C Atom F17 has ADP max/min Ratio ........... 3.20 PLAT_213 Alert C Atom C64 has ADP max/min Ratio ........... 3.50 PLAT_213 Alert C Atom C73 has ADP max/min Ratio ........... 3.80 PLAT_320 Alert C Check Hybridisation of C(70) in main residue ? PLAT_321 Alert C Check Hybridisation of C(1S) in solvent/ion ? PLAT_321 Alert C Check Hybridisation of C(2S) in solvent/ion ? PLAT_369 Alert C Long C(sp2)-C(sp2) Bond C(64) - C(66) = 1.55 Ang. PLAT_369 Alert C Long C(sp2)-C(sp2) Bond C(66) - C(67) = 1.55 Ang. PLAT_721 Alert C Bond Calc 0.99052, Rep 0.98000, Dev. 0.01 Ang. C38 -H38A 1.555 1.555 PLAT_721 Alert C Bond Calc 0.96944, Rep 0.98000, Dev. 0.01 Ang. C38 -H38C 1.555 1.555 PLAT_722 Alert C Angle Calc 108.44, Rep 109.50, Dev. 1.06 Deg. C36 -C38 -H38A 1.555 1.555 1.555 PLAT_722 Alert C Angle Calc 110.85, Rep 109.50, Dev. 1.35 Deg. H38B -C38 -H38C 1.555 1.555 1.555
5 Alert Level A = Potentially serious problem
2 Alert Level B = Potential problem
19 Alert Level C = Please check

Comment top

Previous studies have shown that the reaction of [Zn(hfac)2].2H2O with N-donor heterocyclic ligands produces octahedral metal complexes that contain the Zn(hfac)2 moiety. Examples of compounds that have been crystallographically characterized are, for monodentate ligands, cis-[Zn(hfac)2(pyridine)2] (Pradilla-Sorzano & Fackler, 1973), trans-[Zn(hfac)2(py)2], where py is a substituted pyridine (Lee & Wei, 2000), and for bidentate chelate N-heterocyclic ligands, cis-[Zn(hfac)2(N—N)], where N—N represents a substituted 2,2'-bipyridine ligand (Kumada et al., 2000; Lee & Wei, 2000; Sakane et al., 2000).

To extend the study to the use of terdentate nitrogen ligands, we have investigated the reaction of [Zn(hfac)2].2H2O, with 2,2':6',2''-terpyridine (terpy), 2,6-bis[1-(4-tert-butylphenylimino)ethyl]pyridine (L1) and 2,6-bis[1-(4-methylphenylimino)ethyl]pyridine (L2). The product from the reaction with terpy is [Zn(terpy)2](hfac)2 which was characterized by elemental analysis and 1H NMR studies. In (CD3)2CO solution at 233 K the 1H NMR spectrum is consistent with the formulation [Zn(terpy)2](hfac)2, but at higher temperatures, there is spectral evidence of some intermolecular exchange by virtue of the partial dissociation of the terpy from the zinc and the consequent attachment of the hfac moiety to the metal. In contrast to this, the reaction of [Zn(hfac)2].2H2O with L1 or L2 leads to the isolation of the complexes [ZnL2][Zn(hfac)3]2 (L = L1 or L2) which for L = L1 is the title compound, (I). The structure of (I) (Fig.1) shows that all three Zn atoms are octahedrally coordinated. In the cation, Zn1 is coordinated by two mer-terdentate chelate L1 ligands to form a distorted octahedron. For the coordinated L1 ligands, all the N and C atoms of the ligand skeleton are coplanar (r.m.s. deviations = 0.0507 and 0.0826 for N1/N3- and N4/N6-containing ligands, respectively) with only the substituted phenyl rings being twisted out of the coordination plane (dihedral angles between ligand core and phenyl rings = 85.38, 72.19, 48.86 and 86.74° for rings C1–C6, C20–C25, C30–C35 and C49–C54, respectively). Because of the strain induced in this type of ligand when it is acting as a terdentate chelate (Edwards et al., 1990), the geometry at Zn1 is a distorted octahedron. The angles N3—Zn1—N1 and N4—Zn1—N6 are reduced from the ideal value of 180° to 149.1 (12) and 150.5 (11)°, respectively. The four Nimino—Zn1—Npyridine bite angles are 76.6 (11), 75.4 (11), 73.9 (11) and 74.0 (11)°, which are much reduced from the expected value of 90°. The bond lengths Zn1—Nimine fall in the range 2.15 (3)–2.31 (3) Å, whereas the Zn1—Npyridine distances are shorter at 2.03 (3) and 2.06 (3) Å. Similar ligand distortions are observed in the five-coordinate complex ZnCl2L3, where L3 is 2,6-bis[1-(phenylimino)ethyl]pyridine (Edwards et al., 1990).

The anion moieties of the structure are both composed of three hexafluoroacetylacetonato ligands coordinated octahedrally about a zinc centre with little deformation from idealized geometry. However, these chelating ligands form six-membered rings with the metal centres and have adopted a number of different conformations which have been analysed by puckering analysis (Cremer & Pople, 1975). The chelates around Zn2 form a flat ring (O1–O2 chelate, maximum deviation from mean ring plane = 0.05 Å), an envelope (chelate O3–O4) and a half chair (chelate O5–O6). About Zn3, the rings adopt a flat conformation (O7–O8 chelate, maximum deviation from mean ring plane = 0.027 Å) and envelope conformations for the remaining two ligand ring systems.

Experimental top

A solution of [Zn(hfac)2].2H2O (0.037 g, 0.072 mmol) in diethyl ether was added with stirring to a solution of L1 (0.020 g, 0.047 mmol) (Granifo et al., 1999) in diethyl ether (10 ml). The yellow solution was concentrated to approximately 5 ml and allowed to stand for 6 h. The yellow crystals obtained were washed with diethyl ether (2 × 10 ml) and dried under vacuum. Yield 36 mg, 65%. Analysis for [Zn(L1)2][Zn(hfac)3]2.Et2O, c calculated: C 46.75, H 3.67, N 3.56%; found: C 46.34, H 3.40, N 3.68%. The zinc complexes with terpy or L2 were prepared in a similar fashion. Analyses for [Zn(L2)2][Zn(hfac)3]2, calculated: C 43.03, H 2.47, N 3.96%; found: C 43.06, H 2.47, N 3.89%. Analyses for [Zn(terpy)2](hfac)2, calculated: C 50.78, H 2.56, N 8.88%; found: C 50.79, H 2.34, N 8.84%.

Refinement top

H atoms were located in idealized positions and their coordinates and displacement parameters allowed to ride on those of the parent atom. The refinement required damping in order to prevent parameters from shifting excessively, which is due to a low percentage of observed reflections.

Computing details top

Data collection: MADNES (Pflugrath & Messerschmidt, 1989); cell refinement: MADNES; data reduction: MADNES; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 1990).

Figures top
[Figure 1] Fig. 1. The cation moiety of the title compound (50% probability displacement ellipsoids).
[Figure 2] Fig. 2. The anion moieties of the title compound (50% probability displacement ellipsoids). The CF3 groups have been omitted for clarity.
(I) top
Crystal data top
[Zn(C29H35N3)2][Zn(C5HF6O2)3]2·0.5C4H10OF(000) = 9376
Mr = 2321.68Dx = 1.535 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71069 Å
a = 42.138 (2) ÅCell parameters from 26256 reflections
b = 19.4444 (10) Åθ = 1.8–25.1°
c = 26.255 (2) ŵ = 0.84 mm1
β = 110.969 (10)°T = 150 K
V = 20088 (2) Å3Block, yellow
Z = 80.35 × 0.22 × 0.22 mm
Data collection top
Nonius FAST TV area-detector
diffractometer
6038 reflections with I > 2σ(I)
Radiation source: Nonius FR591 rotating anodeRint = 0.074
ϕ and ω scansθmax = 25.1°, θmin = 1.8°
Absorption correction: part of the refinement model (ΔF)
(DIFABS; Walker & Stuart, 1983)
h = 4749
Tmin = 0.758, Tmax = 0.837k = 1122
26256 measured reflectionsl = 3030
14012 independent reflections
Refinement top
Refinement on F230 restraints
Least-squares matrix: full with fixed elements per cycleH atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.061 w = 1/[σ2(Fo2) + (0.0364P)2]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.129(Δ/σ)max = 1.002
S = 0.76Δρmax = 1.04 e Å3
14012 reflectionsΔρmin = 0.83 e Å3
1348 parameters
Crystal data top
[Zn(C29H35N3)2][Zn(C5HF6O2)3]2·0.5C4H10OV = 20088 (2) Å3
Mr = 2321.68Z = 8
Monoclinic, C2/cMo Kα radiation
a = 42.138 (2) ŵ = 0.84 mm1
b = 19.4444 (10) ÅT = 150 K
c = 26.255 (2) Å0.35 × 0.22 × 0.22 mm
β = 110.969 (10)°
Data collection top
Nonius FAST TV area-detector
diffractometer
14012 independent reflections
Absorption correction: part of the refinement model (ΔF)
(DIFABS; Walker & Stuart, 1983)
6038 reflections with I > 2σ(I)
Tmin = 0.758, Tmax = 0.837Rint = 0.074
26256 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.06130 restraints
wR(F2) = 0.129H atoms treated by a mixture of independent and constrained refinement
S = 0.76(Δ/σ)max = 1.002
14012 reflectionsΔρmax = 1.04 e Å3
1348 parametersΔρmin = 0.83 e Å3
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Zn10.12518 (10)0.2856 (2)0.13642 (18)0.0241 (12)
Zn20.07644 (12)0.2932 (2)0.4155 (2)0.0328 (13)
Zn30.25176 (12)0.5521 (2)0.4847 (2)0.0375 (14)
F10.0963 (9)0.4385 (17)0.2887 (14)0.119 (13)
F20.0461 (9)0.4090 (15)0.2416 (11)0.112 (13)
F30.0562 (9)0.5089 (14)0.2791 (12)0.109 (12)
F40.0253 (8)0.4202 (18)0.3979 (18)0.133 (15)
F50.0025 (9)0.5110 (15)0.4009 (19)0.158 (19)
F60.0105 (11)0.447 (2)0.4674 (15)0.19 (2)
F70.1764 (8)0.3889 (15)0.5354 (14)0.110 (12)
F80.1603 (8)0.3615 (17)0.5954 (14)0.111 (12)
F90.1911 (7)0.2932 (13)0.5762 (15)0.106 (13)
F100.0566 (7)0.1551 (13)0.5551 (12)0.078 (9)
F110.1072 (8)0.135 (2)0.5846 (14)0.151 (17)
F120.0791 (10)0.0883 (16)0.515 (2)0.17 (2)
F130.0093 (8)0.1070 (17)0.3844 (16)0.130 (14)
F140.0364 (6)0.0387 (12)0.3553 (11)0.061 (8)
F150.0047 (6)0.1144 (13)0.3049 (11)0.074 (9)
F160.1691 (8)0.140 (2)0.4669 (15)0.149 (16)
F170.1678 (7)0.1675 (14)0.3876 (16)0.111 (13)
F180.1482 (9)0.0779 (15)0.4038 (14)0.113 (12)
F190.2987 (6)0.4511 (14)0.6590 (10)0.073 (9)
F200.2466 (7)0.4522 (15)0.6468 (11)0.082 (10)
F210.2700 (7)0.3585 (12)0.6390 (10)0.070 (8)
F220.2360 (6)0.3492 (12)0.3889 (10)0.063 (8)
F230.2110 (6)0.3033 (12)0.4378 (10)0.068 (9)
F240.2641 (7)0.2903 (12)0.4580 (11)0.082 (10)
F250.2969 (8)0.7612 (13)0.5867 (13)0.096 (11)
F260.3332 (6)0.7011 (15)0.6464 (12)0.097 (11)
F270.2815 (6)0.6889 (14)0.6334 (11)0.080 (9)
F280.3858 (6)0.5426 (13)0.5682 (10)0.065 (8)
F290.3696 (6)0.5873 (12)0.4881 (11)0.068 (8)
F300.3595 (6)0.4821 (12)0.4980 (11)0.066 (8)
F310.1178 (6)0.5557 (17)0.3817 (13)0.107 (12)
F320.1409 (7)0.4935 (17)0.4519 (14)0.115 (13)
F330.1359 (7)0.6004 (18)0.4616 (14)0.108 (12)
F340.1828 (10)0.594 (3)0.2750 (14)0.24 (3)
F350.2191 (15)0.6609 (19)0.3074 (16)0.193 (14)
F360.2293 (13)0.566 (2)0.2990 (16)0.171 (15)
O10.0767 (7)0.3565 (12)0.3521 (10)0.041 (8)
O20.0393 (6)0.3568 (13)0.4228 (12)0.047 (8)
O30.1159 (6)0.3371 (12)0.4781 (11)0.040 (8)
O40.0700 (6)0.2308 (14)0.4751 (11)0.050 (9)
O50.1140 (6)0.2364 (12)0.4010 (10)0.035 (7)
O60.0448 (6)0.2170 (13)0.3638 (11)0.043 (8)
O70.2607 (7)0.5078 (13)0.5597 (11)0.040 (8)
O80.2430 (6)0.4558 (12)0.4499 (11)0.040 (8)
O90.2691 (6)0.6410 (12)0.5297 (11)0.042 (8)
O100.3015 (6)0.5437 (13)0.4845 (11)0.045 (8)
O110.2009 (6)0.5653 (13)0.4734 (11)0.045 (8)
O120.2395 (6)0.5909 (13)0.4081 (12)0.050 (9)
N10.1557 (7)0.3000 (14)0.2234 (12)0.025 (8)
N20.0917 (7)0.2777 (14)0.1773 (11)0.023 (8)
N30.0763 (7)0.2737 (14)0.0733 (11)0.021 (8)
N40.1344 (7)0.3892 (14)0.1119 (12)0.023 (8)
N50.1633 (7)0.2712 (14)0.1074 (11)0.022 (8)
N60.1366 (7)0.1693 (15)0.1432 (12)0.026 (8)
C10.1912 (10)0.317 (2)0.2415 (16)0.029 (11)
C20.2146 (10)0.265 (2)0.2538 (18)0.043 (13)
H20.20770.21870.25160.051*
C30.2486 (10)0.283 (2)0.2696 (18)0.045 (13)
H30.26480.24640.27770.054*
C40.2602 (10)0.348 (2)0.2741 (16)0.032 (11)
C50.2364 (11)0.397 (2)0.261 (2)0.057 (16)
H50.24330.44410.26310.068*
C60.2019 (11)0.382 (2)0.2446 (19)0.050 (14)
H60.18580.41860.23550.06*
C70.2978 (10)0.368 (2)0.2953 (18)0.037 (12)
C80.3064 (10)0.394 (2)0.3538 (17)0.049 (14)
H8A0.30330.35720.37690.074*
H8B0.29130.43260.35360.074*
H8C0.330.410.36810.074*
C90.3044 (10)0.424 (2)0.2598 (19)0.058 (15)
H9A0.29760.40810.22210.087*
H9B0.32860.43580.27350.087*
H9C0.29110.46520.26120.087*
C100.3205 (9)0.3047 (19)0.2950 (18)0.046 (13)
H10A0.34410.31970.30460.069*
H10B0.31260.2840.25860.069*
H10C0.31910.27070.32170.069*
C110.1404 (9)0.2957 (19)0.2560 (15)0.029 (10)
C120.1551 (10)0.309 (2)0.3163 (16)0.059 (15)
H12A0.16530.26710.33550.088*
H12B0.13710.32490.32890.088*
H12C0.17260.34520.32370.088*
C130.1039 (9)0.2775 (18)0.2317 (15)0.026 (10)
C140.0833 (10)0.261 (2)0.2608 (17)0.037 (11)
H140.09190.26060.29950.044*
C150.0496 (11)0.246 (2)0.2315 (17)0.040 (12)
H150.03480.23340.25010.048*
C160.0372 (10)0.2486 (19)0.1747 (18)0.034 (11)
H160.01380.24070.15430.041*
C170.0599 (9)0.2630 (18)0.1488 (15)0.025 (10)
C180.0512 (9)0.2632 (17)0.0880 (15)0.024 (10)
C190.0154 (9)0.2476 (19)0.0520 (15)0.036 (11)
H19A0.00010.28280.05710.054*
H19B0.00880.20240.06150.054*
H19C0.01370.24730.01380.054*
C200.0717 (8)0.2759 (19)0.0169 (15)0.022 (10)
C210.0557 (9)0.3296 (19)0.0164 (15)0.030 (11)
H210.04720.36690.00170.036*
C220.0518 (10)0.330 (2)0.0709 (16)0.038 (12)
H220.04010.36740.0930.046*
C230.0641 (9)0.279 (2)0.0943 (16)0.033 (11)
C240.0820 (12)0.227 (2)0.0592 (17)0.056 (14)
H240.09150.19030.07330.067*
C250.0862 (11)0.226 (2)0.0049 (17)0.047 (13)
H250.09950.19130.0180.056*
C260.0586 (11)0.275 (2)0.1552 (17)0.046 (13)
C270.0411 (11)0.340 (2)0.1856 (17)0.061 (15)
H27A0.01880.34550.18230.091*
H27B0.03830.33660.22420.091*
H27C0.05510.38070.16970.091*
C280.0925 (10)0.267 (2)0.1628 (17)0.059 (15)
H28A0.08860.26110.20160.089*
H28B0.10450.22710.14240.089*
H28C0.10630.30860.14940.089*
C290.0357 (11)0.211 (3)0.1803 (18)0.073 (16)
H29A0.01410.21560.17430.11*
H29B0.04740.16950.16290.11*
H29C0.03130.20950.21960.11*
C300.1172 (9)0.4506 (19)0.1172 (16)0.028 (10)
C310.1127 (9)0.466 (2)0.1650 (16)0.033 (11)
H310.11980.43450.19430.039*
C320.0980 (9)0.5278 (19)0.1713 (17)0.033 (11)
H320.09690.5390.20580.039*
C330.0851 (9)0.5726 (19)0.1287 (16)0.026 (10)
C340.0880 (10)0.555 (2)0.0801 (16)0.035 (11)
H340.07890.58470.04980.042*
C350.1034 (11)0.495 (2)0.0733 (17)0.041 (12)
H350.10470.48470.03880.049*
C360.0711 (10)0.643 (2)0.1374 (16)0.030 (10)
C370.0455 (10)0.670 (2)0.0840 (16)0.045 (13)
H37A0.02730.63620.06910.067*
H37B0.0570.67750.05780.067*
H37C0.03590.71340.09070.067*
C380.1006 (11)0.694 (2)0.159 (2)0.060 (15)
H38A0.11060.70090.13050.091*
H38B0.11790.6750.19150.091*
H38C0.09220.73750.16710.091*
C390.0535 (11)0.639 (2)0.1785 (19)0.055 (14)
H39A0.04590.6850.18420.082*
H39B0.06940.62110.21320.082*
H39C0.03380.60820.16480.082*
C400.1605 (9)0.393 (2)0.0989 (16)0.033 (11)
C410.1785 (10)0.458 (2)0.0937 (19)0.054 (14)
H41A0.17330.46850.0550.08*
H41B0.20310.45180.11170.08*
H41C0.1710.49630.11090.08*
C420.1758 (9)0.3257 (18)0.0902 (15)0.026 (10)
C430.2000 (9)0.320 (2)0.0660 (17)0.037 (11)
H430.20830.35970.05340.044*
C440.2114 (9)0.255 (2)0.0610 (17)0.039 (12)
H440.22720.2490.04310.046*
C450.2003 (10)0.198 (2)0.0814 (16)0.037 (11)
H450.20890.15340.07920.045*
C460.1764 (9)0.2086 (19)0.1050 (15)0.025 (10)
C470.1622 (9)0.1531 (18)0.1301 (15)0.026 (10)
C480.1786 (10)0.0836 (19)0.1385 (18)0.044 (12)
H48A0.20130.08660.16660.066*
H48B0.18040.06770.10420.066*
H48C0.16470.05110.15010.066*
C490.1218 (10)0.1190 (18)0.1665 (16)0.025 (10)
C500.0941 (11)0.082 (2)0.1352 (18)0.050 (14)
H500.08390.09230.09740.06*
C510.0808 (11)0.031 (2)0.1572 (19)0.053 (14)
H510.0620.00530.1340.063*
C520.0938 (10)0.015 (2)0.2124 (17)0.033 (11)
C530.1208 (10)0.054 (2)0.2448 (17)0.040 (12)
H530.12980.04670.28310.047*
C540.1352 (10)0.106 (2)0.2213 (17)0.036 (12)
H540.15440.13080.24380.043*
C550.0800 (10)0.043 (2)0.2360 (17)0.035 (11)
C560.0427 (13)0.034 (3)0.226 (3)0.12 (3)
H56A0.03420.07350.240.179*
H56B0.03020.02950.18650.179*
H56C0.03950.00810.24420.179*
C570.0841 (15)0.110 (2)0.210 (3)0.11 (3)
H57A0.07990.14840.23060.171*
H57B0.10730.11280.20960.171*
H57C0.06780.11130.17230.171*
C580.0976 (13)0.052 (3)0.298 (2)0.09 (2)
H58A0.08950.09450.30990.138*
H58B0.09230.01280.31710.138*
H58C0.12230.0550.30760.138*
C590.0599 (12)0.411 (2)0.3358 (18)0.048 (13)
C600.0649 (13)0.442 (2)0.286 (2)0.074 (17)
C610.0381 (11)0.441 (2)0.3577 (18)0.046 (13)
H610.02890.48510.34420.055*
C620.0292 (10)0.412 (2)0.3977 (19)0.041 (12)
C630.0045 (11)0.449 (2)0.417 (2)0.066 (15)
C640.1355 (16)0.305 (2)0.515 (2)0.11 (3)
C650.1672 (11)0.334 (2)0.553 (2)0.056 (14)
C660.1240 (13)0.240 (3)0.538 (2)0.10 (2)
H660.13920.21920.57030.119*
C670.0888 (14)0.206 (3)0.510 (2)0.09 (2)
C680.0828 (10)0.145 (2)0.5405 (19)0.048 (13)
C690.0334 (16)0.105 (2)0.341 (3)0.16 (4)
C700.0523 (13)0.156 (2)0.371 (2)0.071 (17)
C710.0878 (17)0.128 (3)0.386 (2)0.09 (2)
H710.09160.08040.38430.111*
C720.120 (2)0.183 (4)0.407 (3)0.17 (4)
C730.1503 (13)0.144 (2)0.416 (2)0.068 (16)
C740.2598 (9)0.444 (2)0.5679 (16)0.035 (11)
C750.2684 (11)0.427 (2)0.6279 (17)0.045 (12)
C760.2537 (10)0.389 (2)0.5309 (17)0.037 (12)
H760.25480.34320.54410.044*
C770.2460 (9)0.4003 (19)0.4747 (17)0.032 (11)
C780.2389 (11)0.335 (2)0.4397 (17)0.047 (13)
C790.2983 (10)0.646 (2)0.5632 (19)0.043 (12)
C800.3035 (11)0.700 (2)0.608 (2)0.062 (15)
C810.3276 (10)0.612 (2)0.5629 (19)0.043 (13)
H810.34870.62040.59140.051*
C820.3264 (10)0.565 (2)0.5220 (19)0.042 (12)
C830.3608 (11)0.5441 (19)0.5201 (19)0.047 (13)
C840.1783 (11)0.563 (2)0.428 (2)0.047 (13)
C850.1425 (12)0.551 (3)0.430 (2)0.074 (17)
C860.1802 (11)0.573 (2)0.3763 (19)0.048 (13)
H860.16020.56870.34470.058*
C870.2118 (12)0.5894 (19)0.3705 (18)0.044 (13)
C880.2098 (12)0.603 (2)0.315 (2)0.060 (14)
O1S000.50.26 (3)
C1S0.017 (3)0.047 (5)0.482 (4)0.21 (3)
C2S0.019 (3)0.089 (5)0.448 (6)0.28 (4)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Zn10.022 (3)0.031 (3)0.020 (3)0.001 (2)0.008 (2)0.001 (2)
Zn20.035 (3)0.032 (3)0.035 (3)0.007 (2)0.017 (3)0.006 (3)
Zn30.039 (3)0.030 (3)0.045 (3)0.002 (3)0.018 (3)0.001 (3)
F10.16 (3)0.12 (3)0.11 (3)0.03 (2)0.09 (3)0.06 (2)
F20.19 (4)0.09 (2)0.035 (19)0.02 (2)0.02 (2)0.010 (16)
F30.23 (4)0.05 (2)0.08 (2)0.03 (2)0.09 (3)0.035 (17)
F40.08 (3)0.13 (3)0.22 (5)0.01 (2)0.09 (3)0.03 (3)
F50.18 (4)0.04 (2)0.34 (6)0.06 (2)0.20 (4)0.07 (3)
F60.19 (4)0.28 (5)0.08 (3)0.18 (4)0.04 (3)0.01 (3)
F70.09 (3)0.10 (3)0.13 (3)0.031 (19)0.03 (2)0.03 (2)
F80.09 (3)0.13 (3)0.11 (3)0.00 (2)0.03 (2)0.04 (2)
F90.06 (2)0.06 (2)0.17 (3)0.016 (16)0.00 (2)0.02 (2)
F100.09 (2)0.07 (2)0.12 (3)0.011 (15)0.08 (2)0.022 (18)
F110.09 (3)0.24 (5)0.09 (3)0.00 (3)0.02 (2)0.04 (3)
F120.17 (4)0.07 (3)0.32 (6)0.05 (2)0.16 (4)0.10 (3)
F130.10 (3)0.12 (3)0.16 (4)0.02 (2)0.04 (3)0.02 (3)
F140.054 (17)0.048 (17)0.08 (2)0.009 (13)0.024 (16)0.013 (15)
F150.06 (2)0.08 (2)0.06 (2)0.010 (16)0.001 (17)0.013 (16)
F160.07 (3)0.24 (5)0.11 (3)0.03 (3)0.00 (2)0.03 (3)
F170.10 (3)0.07 (2)0.22 (4)0.026 (18)0.13 (3)0.03 (2)
F180.15 (3)0.08 (3)0.11 (3)0.04 (2)0.06 (3)0.00 (2)
F190.055 (18)0.12 (2)0.030 (16)0.001 (17)0.004 (14)0.016 (16)
F200.08 (2)0.12 (3)0.06 (2)0.055 (18)0.044 (17)0.020 (18)
F210.11 (2)0.059 (19)0.046 (18)0.006 (16)0.028 (17)0.014 (14)
F220.09 (2)0.060 (18)0.041 (17)0.015 (15)0.026 (16)0.009 (14)
F230.08 (2)0.063 (19)0.053 (18)0.043 (15)0.017 (16)0.011 (14)
F240.10 (2)0.047 (18)0.08 (2)0.018 (16)0.004 (18)0.026 (16)
F250.13 (3)0.045 (19)0.12 (3)0.024 (17)0.06 (2)0.031 (18)
F260.046 (18)0.13 (3)0.10 (3)0.006 (17)0.010 (18)0.06 (2)
F270.06 (2)0.11 (3)0.08 (2)0.001 (16)0.032 (17)0.021 (18)
F280.047 (17)0.08 (2)0.060 (19)0.011 (14)0.014 (15)0.004 (16)
F290.056 (19)0.068 (19)0.09 (2)0.001 (14)0.038 (17)0.019 (16)
F300.055 (18)0.060 (19)0.09 (2)0.008 (13)0.039 (17)0.011 (16)
F310.036 (18)0.18 (3)0.09 (3)0.023 (19)0.002 (17)0.03 (2)
F320.07 (2)0.13 (3)0.14 (3)0.028 (19)0.04 (2)0.06 (2)
F330.05 (2)0.16 (3)0.12 (3)0.019 (19)0.03 (2)0.01 (2)
F340.09 (3)0.57 (9)0.04 (3)0.10 (4)0.01 (2)0.06 (4)
F350.429 (16)0.090 (15)0.093 (15)0.034 (6)0.134 (8)0.007 (6)
F360.271 (16)0.170 (16)0.105 (15)0.086 (6)0.107 (8)0.010 (6)
O10.06 (2)0.035 (18)0.032 (18)0.012 (14)0.025 (16)0.007 (14)
O20.044 (19)0.041 (19)0.07 (2)0.014 (14)0.032 (17)0.017 (16)
O30.05 (2)0.032 (17)0.037 (18)0.004 (14)0.015 (16)0.001 (14)
O40.043 (19)0.07 (2)0.05 (2)0.019 (15)0.028 (16)0.028 (17)
O50.035 (17)0.037 (18)0.035 (18)0.016 (13)0.015 (15)0.008 (14)
O60.032 (17)0.035 (18)0.06 (2)0.010 (14)0.008 (15)0.001 (16)
O70.05 (2)0.038 (18)0.034 (18)0.002 (14)0.015 (15)0.003 (14)
O80.049 (19)0.028 (17)0.037 (18)0.001 (14)0.008 (15)0.011 (14)
O90.036 (18)0.031 (18)0.06 (2)0.001 (14)0.018 (16)0.002 (15)
O100.039 (18)0.046 (19)0.05 (2)0.003 (14)0.020 (16)0.004 (16)
O110.039 (19)0.05 (2)0.05 (2)0.001 (14)0.015 (16)0.006 (16)
O120.023 (17)0.05 (2)0.06 (2)0.000 (14)0.008 (16)0.017 (17)
N10.027 (19)0.02 (2)0.026 (19)0.010 (16)0.011 (16)0.001 (16)
N20.016 (17)0.03 (2)0.017 (17)0.004 (14)0.002 (15)0.005 (15)
N30.018 (17)0.03 (2)0.014 (17)0.006 (14)0.002 (15)0.001 (15)
N40.019 (18)0.03 (2)0.03 (2)0.002 (15)0.012 (16)0.005 (15)
N50.020 (18)0.02 (2)0.018 (18)0.002 (14)0.002 (15)0.000 (15)
N60.03 (2)0.03 (2)0.022 (19)0.005 (15)0.009 (16)0.001 (16)
C10.03 (3)0.02 (3)0.03 (3)0.01 (2)0.00 (2)0.00 (2)
C20.03 (3)0.02 (3)0.07 (4)0.00 (2)0.01 (3)0.01 (2)
C30.03 (3)0.03 (3)0.07 (3)0.00 (2)0.01 (3)0.00 (3)
C40.02 (3)0.03 (3)0.03 (3)0.00 (2)0.00 (2)0.00 (2)
C50.04 (3)0.02 (3)0.10 (5)0.01 (3)0.02 (3)0.01 (3)
C60.03 (3)0.04 (3)0.07 (4)0.00 (2)0.00 (3)0.00 (3)
C70.02 (3)0.04 (3)0.04 (3)0.01 (2)0.00 (2)0.00 (2)
C80.03 (3)0.04 (3)0.06 (4)0.01 (2)0.01 (3)0.01 (3)
C90.04 (3)0.06 (3)0.07 (4)0.02 (2)0.01 (3)0.01 (3)
C100.03 (3)0.04 (3)0.07 (4)0.00 (2)0.02 (3)0.00 (3)
C110.02 (2)0.03 (3)0.03 (2)0.00 (2)0.00 (2)0.00 (2)
C120.04 (3)0.10 (4)0.03 (3)0.00 (3)0.01 (2)0.01 (3)
C130.02 (2)0.03 (3)0.03 (2)0.002 (19)0.01 (2)0.00 (2)
C140.03 (3)0.05 (3)0.02 (3)0.00 (2)0.01 (2)0.00 (2)
C150.04 (3)0.05 (3)0.03 (3)0.01 (2)0.02 (3)0.00 (2)
C160.02 (3)0.04 (3)0.04 (3)0.00 (2)0.01 (2)0.00 (2)
C170.03 (2)0.02 (2)0.03 (2)0.004 (18)0.01 (2)0.003 (19)
C180.03 (2)0.02 (2)0.03 (2)0.003 (18)0.01 (2)0.003 (19)
C190.03 (3)0.04 (3)0.02 (2)0.01 (2)0.00 (2)0.01 (2)
C200.01 (2)0.03 (3)0.02 (2)0.003 (19)0.001 (19)0.00 (2)
C210.04 (3)0.03 (3)0.02 (2)0.01 (2)0.00 (2)0.00 (2)
C220.05 (3)0.05 (3)0.03 (3)0.02 (2)0.02 (2)0.02 (2)
C230.03 (2)0.04 (3)0.03 (2)0.00 (2)0.01 (2)0.00 (2)
C240.08 (4)0.06 (3)0.03 (3)0.04 (3)0.02 (3)0.00 (3)
C250.06 (3)0.05 (3)0.03 (3)0.03 (3)0.01 (3)0.01 (2)
C260.05 (3)0.08 (4)0.02 (3)0.02 (3)0.02 (2)0.01 (3)
C270.06 (4)0.09 (4)0.03 (3)0.04 (3)0.02 (3)0.02 (3)
C280.06 (3)0.09 (4)0.03 (3)0.03 (3)0.02 (3)0.00 (3)
C290.06 (4)0.11 (5)0.03 (3)0.00 (3)0.01 (3)0.02 (3)
C300.03 (2)0.02 (2)0.03 (3)0.01 (2)0.01 (2)0.00 (2)
C310.04 (3)0.05 (3)0.02 (2)0.00 (2)0.01 (2)0.01 (2)
C320.04 (3)0.03 (3)0.04 (3)0.01 (2)0.02 (2)0.01 (2)
C330.03 (2)0.03 (3)0.03 (3)0.01 (2)0.01 (2)0.00 (2)
C340.05 (3)0.03 (3)0.02 (3)0.01 (2)0.02 (2)0.01 (2)
C350.07 (3)0.04 (3)0.03 (3)0.01 (3)0.03 (3)0.00 (2)
C360.04 (3)0.03 (3)0.03 (3)0.00 (2)0.02 (2)0.00 (2)
C370.05 (3)0.04 (3)0.04 (3)0.02 (2)0.02 (3)0.00 (2)
C380.06 (3)0.03 (3)0.09 (4)0.00 (2)0.02 (3)0.02 (3)
C390.07 (4)0.04 (3)0.07 (4)0.02 (2)0.05 (3)0.01 (3)
C400.02 (2)0.03 (3)0.04 (3)0.00 (2)0.00 (2)0.00 (2)
C410.05 (3)0.04 (3)0.09 (4)0.01 (2)0.04 (3)0.00 (3)
C420.03 (2)0.01 (2)0.03 (3)0.007 (19)0.01 (2)0.007 (19)
C430.03 (3)0.03 (3)0.06 (3)0.01 (2)0.02 (2)0.00 (2)
C440.03 (3)0.04 (3)0.05 (3)0.00 (2)0.03 (2)0.01 (3)
C450.03 (3)0.04 (3)0.04 (3)0.00 (2)0.01 (2)0.01 (2)
C460.02 (2)0.03 (2)0.02 (2)0.00 (2)0.00 (2)0.00 (2)
C470.03 (2)0.02 (2)0.03 (2)0.005 (19)0.00 (2)0.00 (2)
C480.05 (3)0.04 (3)0.06 (3)0.02 (2)0.03 (3)0.01 (2)
C490.03 (3)0.02 (2)0.02 (2)0.00 (2)0.01 (2)0.00 (2)
C500.05 (3)0.06 (4)0.02 (3)0.02 (3)0.00 (3)0.00 (3)
C510.06 (3)0.05 (3)0.04 (3)0.03 (3)0.00 (3)0.00 (3)
C520.02 (3)0.04 (3)0.04 (3)0.01 (2)0.01 (2)0.01 (2)
C530.05 (3)0.04 (3)0.03 (3)0.00 (2)0.01 (2)0.00 (2)
C540.03 (3)0.04 (3)0.03 (3)0.01 (2)0.00 (2)0.00 (2)
C550.05 (3)0.03 (3)0.04 (3)0.00 (2)0.02 (2)0.00 (2)
C560.07 (4)0.10 (5)0.21 (8)0.03 (3)0.08 (5)0.08 (5)
C570.19 (7)0.03 (3)0.19 (7)0.03 (4)0.15 (6)0.01 (4)
C580.12 (5)0.10 (5)0.06 (4)0.05 (4)0.03 (4)0.02 (3)
C590.07 (4)0.04 (3)0.03 (3)0.00 (3)0.01 (3)0.00 (2)
C600.11 (5)0.06 (4)0.05 (3)0.02 (3)0.03 (3)0.02 (3)
C610.06 (3)0.03 (3)0.04 (3)0.00 (3)0.02 (3)0.00 (2)
C620.05 (3)0.03 (3)0.06 (3)0.01 (2)0.03 (3)0.01 (2)
C630.05 (3)0.08 (4)0.08 (4)0.02 (3)0.04 (3)0.01 (3)
C640.15 (6)0.03 (3)0.08 (5)0.03 (4)0.04 (4)0.00 (3)
C650.05 (3)0.05 (3)0.07 (4)0.01 (3)0.01 (3)0.01 (3)
C660.04 (4)0.13 (6)0.10 (5)0.01 (4)0.01 (4)0.02 (4)
C670.09 (5)0.12 (5)0.11 (5)0.07 (4)0.08 (4)0.07 (4)
C680.04 (3)0.04 (3)0.07 (3)0.00 (2)0.02 (3)0.01 (3)
C690.14 (6)0.01 (3)0.17 (7)0.03 (3)0.15 (5)0.03 (3)
C700.04 (4)0.05 (4)0.09 (4)0.00 (3)0.01 (3)0.01 (3)
C710.14 (6)0.07 (4)0.10 (5)0.00 (4)0.08 (5)0.00 (4)
C720.21 (8)0.17 (7)0.24 (9)0.16 (7)0.22 (7)0.18 (7)
C730.11 (4)0.03 (3)0.10 (4)0.04 (3)0.08 (4)0.02 (3)
C740.02 (2)0.06 (3)0.02 (2)0.00 (2)0.00 (2)0.00 (2)
C750.06 (3)0.04 (3)0.04 (3)0.00 (2)0.02 (3)0.00 (2)
C760.04 (3)0.03 (3)0.04 (3)0.01 (2)0.01 (2)0.02 (2)
C770.02 (3)0.03 (3)0.04 (3)0.01 (2)0.01 (2)0.01 (2)
C780.06 (3)0.03 (3)0.04 (3)0.01 (2)0.00 (3)0.01 (2)
C790.04 (3)0.04 (3)0.06 (4)0.01 (2)0.03 (3)0.01 (2)
C800.05 (3)0.06 (3)0.07 (4)0.01 (3)0.02 (3)0.03 (3)
C810.03 (3)0.04 (3)0.06 (3)0.01 (2)0.01 (3)0.01 (3)
C820.05 (3)0.02 (3)0.06 (3)0.01 (2)0.03 (3)0.00 (2)
C830.05 (3)0.02 (3)0.08 (4)0.01 (2)0.04 (3)0.00 (2)
C840.05 (3)0.03 (3)0.07 (4)0.01 (2)0.02 (3)0.01 (3)
C850.05 (3)0.10 (4)0.07 (4)0.01 (3)0.02 (3)0.02 (3)
C860.04 (3)0.06 (3)0.04 (3)0.00 (2)0.01 (3)0.00 (3)
C870.08 (4)0.01 (2)0.05 (3)0.01 (2)0.03 (3)0.00 (2)
C880.07 (4)0.06 (4)0.05 (3)0.01 (3)0.03 (3)0.02 (3)
O1S0.10 (3)0.09 (3)0.60 (3)0.030 (6)0.127 (11)0.154 (6)
C1S0.31 (3)0.16 (3)0.15 (3)0.141 (6)0.076 (13)0.038 (6)
C2S0.21 (4)0.22 (4)0.49 (4)0.096 (6)0.207 (16)0.193 (6)
Geometric parameters (Å, º) top
Zn1—N52.03 (3)C20—C211.37 (5)
Zn1—N22.06 (3)C21—C221.38 (5)
Zn1—N32.15 (3)C21—H210.95
Zn1—N42.19 (3)C22—C231.37 (5)
Zn1—N12.20 (3)C22—H220.95
Zn1—N62.31 (3)C23—C241.40 (5)
Zn2—O22.06 (3)C23—C261.53 (5)
Zn2—O32.06 (3)C24—C251.37 (6)
Zn2—O12.07 (3)C24—H240.95
Zn2—O52.07 (3)C25—H250.95
Zn2—O42.07 (3)C26—C281.52 (6)
Zn2—O62.13 (3)C26—C271.54 (6)
Zn3—O122.03 (3)C26—C291.57 (6)
Zn3—O82.06 (3)C27—H27A0.98
Zn3—O72.06 (3)C27—H27B0.98
Zn3—O112.07 (3)C27—H27C0.98
Zn3—O92.07 (3)C28—H28A0.98
Zn3—O102.10 (3)C28—H28B0.98
F1—C601.30 (6)C28—H28C0.98
F2—C601.32 (5)C29—H29A0.98
F3—C601.34 (5)C29—H29B0.98
F4—C631.30 (5)C29—H29C0.98
F5—C631.27 (5)C30—C311.37 (5)
F6—C631.26 (5)C30—C351.40 (5)
F7—C651.27 (5)C31—C321.38 (5)
F8—C651.35 (5)C31—H310.95
F9—C651.26 (5)C32—C331.37 (5)
F10—C681.30 (5)C32—H320.95
F11—C681.26 (4)C33—C341.37 (5)
F12—C681.27 (5)C33—C361.54 (5)
F13—C691.77 (9)C34—C351.36 (5)
F14—C691.33 (5)C34—H340.95
F15—C691.26 (5)C35—H350.95
F16—C731.29 (6)C36—C391.52 (6)
F17—C731.30 (5)C36—C371.52 (5)
F18—C731.32 (5)C36—C381.53 (5)
F19—C751.33 (4)C37—H37A0.98
F20—C751.29 (5)C37—H37B0.98
F21—C751.35 (4)C37—H37C0.98
F22—C781.32 (5)C38—H38A0.98
F23—C781.31 (5)C38—H38B0.98
F24—C781.32 (4)C38—H38C0.98
F25—C801.30 (5)C39—H39A0.98
F26—C801.29 (5)C39—H39B0.98
F27—C801.33 (5)C39—H39C0.98
F28—C831.32 (5)C40—C411.50 (5)
F29—C831.33 (4)C40—C421.52 (5)
F30—C831.33 (4)C41—H41A0.98
F31—C851.33 (5)C41—H41B0.98
F32—C851.27 (5)C41—H41C0.98
F33—C851.35 (6)C42—C431.38 (5)
F34—C881.25 (5)C43—C441.38 (5)
F35—C881.23 (5)C43—H430.95
F36—C881.26 (5)C44—C451.38 (5)
O1—C591.26 (5)C44—H440.95
O2—C621.25 (4)C45—C461.37 (5)
O3—C641.21 (5)C45—H450.95
O4—C671.08 (5)C46—C471.50 (5)
O5—C721.08 (7)C47—C481.50 (5)
O6—C701.24 (5)C48—H48A0.98
O7—C741.25 (4)C48—H48B0.98
O8—C771.24 (4)C48—H48C0.98
O9—C791.23 (4)C49—C501.37 (5)
O10—C821.23 (5)C49—C541.37 (5)
O11—C841.24 (5)C50—C511.37 (6)
O12—C871.23 (5)C50—H500.95
N1—C111.24 (4)C51—C521.39 (6)
N1—C11.44 (4)C51—H510.95
N2—C171.31 (4)C52—C531.38 (5)
N2—C131.33 (4)C52—C551.51 (5)
N3—C181.27 (4)C53—C541.42 (5)
N3—C201.42 (4)C53—H530.95
N4—C401.27 (4)C54—H540.95
N4—C301.43 (4)C55—C571.50 (6)
N5—C421.33 (4)C55—C561.51 (6)
N5—C461.35 (4)C55—C581.55 (6)
N6—C471.28 (4)C56—H56A0.98
N6—C491.41 (4)C56—H56B0.98
C1—C61.34 (5)C56—H56C0.98
C1—C21.36 (5)C57—H57A0.98
C2—C31.38 (5)C57—H57B0.98
C2—H20.95C57—H57C0.98
C3—C41.35 (5)C58—H58A0.98
C3—H30.95C58—H58B0.98
C4—C51.35 (5)C58—H58C0.98
C4—C71.53 (5)C59—C611.38 (6)
C5—C61.39 (5)C59—C601.53 (7)
C5—H50.95C61—C621.36 (6)
C6—H60.95C61—H610.95
C7—C91.53 (6)C62—C631.49 (6)
C7—C81.54 (6)C64—C651.47 (6)
C7—C101.55 (5)C64—C661.55 (8)
C8—H8A0.98C66—C671.54 (7)
C8—H8B0.98C66—H660.95
C8—H8C0.98C67—C681.51 (6)
C9—H9A0.98C69—C701.34 (6)
C9—H9B0.98C70—C711.50 (7)
C9—H9C0.98C71—C721.65 (10)
C10—H10A0.98C71—H710.95
C10—H10B0.98C72—C731.42 (6)
C10—H10C0.98C74—C761.41 (5)
C11—C131.48 (5)C74—C751.53 (6)
C11—C121.50 (5)C76—C771.41 (6)
C12—H12A0.98C76—H760.95
C12—H12B0.98C77—C781.53 (5)
C12—H12C0.98C79—C811.41 (5)
C13—C141.38 (5)C79—C801.54 (6)
C14—C151.38 (5)C81—C821.39 (6)
C14—H140.95C81—H810.95
C15—C161.39 (5)C82—C831.53 (6)
C15—H150.95C84—C861.40 (6)
C16—C171.39 (5)C84—C851.55 (6)
C16—H160.95C86—C871.43 (6)
C17—C181.50 (5)C86—H860.95
C18—C191.50 (5)C87—C881.47 (6)
C19—H19A0.98O1S—C1S1.35 (12)
C19—H19B0.98O1S—C1Si1.35 (12)
C19—H19C0.98C1S—C2S1.24 (16)
C20—C251.37 (5)
N5—Zn1—N2165.2 (11)C36—C37—H37C109.5
N5—Zn1—N3111.5 (11)H37A—C37—H37C109.5
N2—Zn1—N375.4 (11)H37B—C37—H37C109.5
N5—Zn1—N476.6 (11)C36—C38—H38A109.5
N2—Zn1—N4116.6 (11)C36—C38—H38B109.5
N3—Zn1—N495.4 (11)H38A—C38—H38B109.5
N5—Zn1—N199.2 (12)C36—C38—H38C109.5
N2—Zn1—N174.0 (11)H38A—C38—H38C109.5
N3—Zn1—N1149.1 (12)H38B—C38—H38C109.5
N4—Zn1—N195.1 (11)C36—C39—H39A109.5
N5—Zn1—N673.9 (11)C36—C39—H39B109.4
N2—Zn1—N692.9 (11)H39A—C39—H39B109.5
N3—Zn1—N694.1 (10)C36—C39—H39C109.5
N4—Zn1—N6150.5 (11)H39A—C39—H39C109.5
N1—Zn1—N690.9 (11)H39B—C39—H39C109.5
O2—Zn2—O395.7 (11)N4—C40—C41127 (4)
O2—Zn2—O186.6 (11)N4—C40—C42116 (3)
O3—Zn2—O199.3 (11)C41—C40—C42117 (4)
O2—Zn2—O5173.5 (11)C40—C41—H41A109.5
O3—Zn2—O585.2 (11)C40—C41—H41B109.5
O1—Zn2—O586.9 (11)H41A—C41—H41B109.5
O2—Zn2—O488.4 (11)C40—C41—H41C109.5
O3—Zn2—O485.7 (11)H41A—C41—H41C109.5
O1—Zn2—O4173.2 (11)H41B—C41—H41C109.5
O5—Zn2—O498.1 (11)N5—C42—C43123 (3)
O2—Zn2—O698.8 (11)N5—C42—C40113 (3)
O3—Zn2—O6160.3 (10)C43—C42—C40124 (4)
O1—Zn2—O694.8 (11)C42—C43—C44117 (4)
O5—Zn2—O681.8 (10)C42—C43—H43121.6
O4—Zn2—O681.5 (12)C44—C43—H43121.6
O12—Zn3—O887.5 (11)C45—C44—C43122 (4)
O12—Zn3—O7175.3 (11)C45—C44—H44119.2
O8—Zn3—O789.2 (11)C43—C44—H44119.2
O12—Zn3—O1186.0 (11)C46—C45—C44117 (4)
O8—Zn3—O1192.2 (11)C46—C45—H45121.4
O7—Zn3—O1190.8 (11)C44—C45—H45121.4
O12—Zn3—O999.6 (11)N5—C46—C45122 (4)
O8—Zn3—O9169.1 (11)N5—C46—C47113 (3)
O7—Zn3—O984.0 (11)C45—C46—C47124 (4)
O11—Zn3—O996.4 (11)N6—C47—C48125 (3)
O12—Zn3—O1085.8 (11)N6—C47—C46117 (3)
O8—Zn3—O1087.1 (11)C48—C47—C46119 (4)
O7—Zn3—O1097.4 (11)C47—C48—H48A109.5
O11—Zn3—O10171.8 (12)C47—C48—H48B109.5
O9—Zn3—O1085.3 (11)H48A—C48—H48B109.5
C59—O1—Zn2127 (2)C47—C48—H48C109.5
C62—O2—Zn2126 (2)H48A—C48—H48C109.5
C64—O3—Zn2124 (2)H48B—C48—H48C109.5
C67—O4—Zn2130 (3)C50—C49—C54118 (4)
C72—O5—Zn2131 (3)C50—C49—N6121 (4)
C70—O6—Zn2120 (3)C54—C49—N6120 (3)
C74—O7—Zn3124.6 (19)C49—C50—C51121 (4)
C77—O8—Zn3126 (2)C49—C50—H50119.4
C79—O9—Zn3122 (2)C51—C50—H50119.4
C82—O10—Zn3123 (2)C50—C51—C52122 (4)
C84—O11—Zn3122 (2)C50—C51—H51119
C87—O12—Zn3128 (2)C52—C51—H51118.9
C11—N1—C1121 (3)C53—C52—C51117 (4)
C11—N1—Zn1116.8 (19)C53—C52—C55121 (4)
C1—N1—Zn1122 (2)C51—C52—C55122 (4)
C17—N2—C13122 (2)C52—C53—C54120 (4)
C17—N2—Zn1117.9 (18)C52—C53—H53119.9
C13—N2—Zn1118.9 (17)C54—C53—H53119.9
C18—N3—C20120 (2)C49—C54—C53121 (4)
C18—N3—Zn1117.2 (18)C49—C54—H54119.6
C20—N3—Zn1122.4 (17)C53—C54—H54119.6
C40—N4—C30119 (2)C57—C55—C56108 (4)
C40—N4—Zn1113.7 (18)C57—C55—C52110 (4)
C30—N4—Zn1126.2 (18)C56—C55—C52111 (4)
C42—N5—C46119 (2)C57—C55—C58107 (4)
C42—N5—Zn1118.7 (18)C56—C55—C58106 (4)
C46—N5—Zn1122.4 (19)C52—C55—C58114 (4)
C47—N6—C49119 (2)C55—C56—H56A109.5
C47—N6—Zn1113.1 (18)C55—C56—H56B109.4
C49—N6—Zn1126.8 (19)H56A—C56—H56B109.5
C6—C1—C2119 (4)C55—C56—H56C109.5
C6—C1—N1122 (4)H56A—C56—H56C109.5
C2—C1—N1119 (4)H56B—C56—H56C109.5
C1—C2—C3118 (4)C55—C57—H57A109.5
C1—C2—H2120.8C55—C57—H57B109.5
C3—C2—H2120.8H57A—C57—H57B109.5
C4—C3—C2124 (4)C55—C57—H57C109.5
C4—C3—H3118H57A—C57—H57C109.5
C2—C3—H3118H57B—C57—H57C109.5
C5—C4—C3116 (4)C55—C58—H58A109.5
C5—C4—C7120 (4)C55—C58—H58B109.5
C3—C4—C7124 (4)H58A—C58—H58B109.5
C4—C5—C6122 (4)C55—C58—H58C109.5
C4—C5—H5119H58A—C58—H58C109.5
C6—C5—H5119H58B—C58—H58C109.5
C1—C6—C5121 (4)O1—C59—C61127 (4)
C1—C6—H6119.6O1—C59—C60113 (4)
C5—C6—H6119.6C61—C59—C60120 (4)
C4—C7—C9110 (3)F1—C60—F2107 (4)
C4—C7—C8107 (4)F1—C60—F3107 (4)
C9—C7—C8110 (4)F2—C60—F3108 (3)
C4—C7—C10111 (3)F1—C60—C59112 (4)
C9—C7—C10109 (4)F2—C60—C59110 (4)
C8—C7—C10110 (4)F3—C60—C59113 (4)
C7—C8—H8A109.5C62—C61—C59124 (5)
C7—C8—H8B109.5C62—C61—H61118.2
H8A—C8—H8B109.5C59—C61—H61118.2
C7—C8—H8C109.5O2—C62—C61129 (4)
H8A—C8—H8C109.5O2—C62—C63113 (4)
H8B—C8—H8C109.5C61—C62—C63118 (4)
C7—C9—H9A109.5F6—C63—F5108 (4)
C7—C9—H9B109.5F6—C63—F4101 (4)
H9A—C9—H9B109.5F5—C63—F4102 (3)
C7—C9—H9C109.5F6—C63—C62116 (4)
H9A—C9—H9C109.5F5—C63—C62117 (4)
H9B—C9—H9C109.5F4—C63—C62111 (4)
C7—C10—H10A109.5O3—C64—C65122 (5)
C7—C10—H10B109.5O3—C64—C66121 (5)
H10A—C10—H10B109.5C65—C64—C66113 (5)
C7—C10—H10C109.5F9—C65—F7114 (4)
H10A—C10—H10C109.5F9—C65—F8103 (3)
H10B—C10—H10C109.5F7—C65—F899 (3)
N1—C11—C13116 (3)F9—C65—C64117 (4)
N1—C11—C12126 (3)F7—C65—C64113 (4)
C13—C11—C12118 (4)F8—C65—C64107 (5)
C11—C12—H12A109.5C67—C66—C64123 (5)
C11—C12—H12B109.5C67—C66—H66118.6
H12A—C12—H12B109.5C64—C66—H66118.7
C11—C12—H12C109.5O4—C67—C68126 (6)
H12A—C12—H12C109.5O4—C67—C66120 (6)
H12B—C12—H12C109.5C68—C67—C66113 (5)
N2—C13—C14121 (3)F11—C68—F12106 (3)
N2—C13—C11114 (3)F11—C68—F10105 (4)
C14—C13—C11125 (4)F12—C68—F10109 (3)
C13—C14—C15118 (4)F11—C68—C67112 (4)
C13—C14—H14121.1F12—C68—C67114 (4)
C15—C14—H14121.1F10—C68—C67111 (3)
C14—C15—C16120 (4)F15—C69—F14109 (4)
C14—C15—H15119.9F15—C69—C70123 (5)
C16—C15—H15119.9F14—C69—C70125 (5)
C17—C16—C15118 (4)F15—C69—F1382 (4)
C17—C16—H16120.9F14—C69—F1382 (4)
C15—C16—H16120.9C70—C69—F1388 (5)
N2—C17—C16120 (4)O6—C70—C69124 (5)
N2—C17—C18115 (3)O6—C70—C71124 (5)
C16—C17—C18125 (4)C69—C70—C71103 (6)
N3—C18—C19127 (3)C70—C71—C72119 (5)
N3—C18—C17114 (3)C70—C71—H71120.5
C19—C18—C17119 (3)C72—C71—H71120.4
C18—C19—H19A109.4O5—C72—C73134 (8)
C18—C19—H19B109.5O5—C72—C71117 (6)
H19A—C19—H19B109.5C73—C72—C71107 (6)
C18—C19—H19C109.5F16—C73—F17110 (4)
H19A—C19—H19C109.5F16—C73—F1899 (3)
H19B—C19—H19C109.5F17—C73—F18102 (3)
C25—C20—C21117 (4)F16—C73—C72112 (5)
C25—C20—N3120 (3)F17—C73—C72112 (4)
C21—C20—N3123 (3)F18—C73—C72120 (6)
C20—C21—C22121 (4)O7—C74—C76130 (4)
C20—C21—H21119.6O7—C74—C75113 (3)
C22—C21—H21119.6C76—C74—C75117 (4)
C23—C22—C21123 (4)F20—C75—F19107 (3)
C23—C22—H22118.7F20—C75—F21106 (3)
C21—C22—H22118.7F19—C75—F21105 (3)
C22—C23—C24116 (4)F20—C75—C74112 (3)
C22—C23—C26124 (4)F19—C75—C74112 (4)
C24—C23—C26120 (4)F21—C75—C74115 (3)
C25—C24—C23122 (4)C77—C76—C74121 (4)
C25—C24—H24119.1C77—C76—H76119.5
C23—C24—H24119.1C74—C76—H76119.5
C24—C25—C20121 (4)O8—C77—C76129 (4)
C24—C25—H25119.3O8—C77—C78116 (4)
C20—C25—H25119.3C76—C77—C78115 (4)
C28—C26—C23110 (4)F23—C78—F22108 (3)
C28—C26—C27108 (4)F23—C78—F24107 (3)
C23—C26—C27112 (4)F22—C78—F24106 (3)
C28—C26—C29109 (4)F23—C78—C77113 (4)
C23—C26—C29108 (4)F22—C78—C77111 (3)
C27—C26—C29109 (4)F24—C78—C77112 (3)
C26—C27—H27A109.4O9—C79—C81127 (4)
C26—C27—H27B109.5O9—C79—C80116 (4)
H27A—C27—H27B109.5C81—C79—C80116 (4)
C26—C27—H27C109.5F26—C80—F25109 (3)
H27A—C27—H27C109.5F26—C80—F27106 (4)
H27B—C27—H27C109.5F25—C80—F27107 (3)
C26—C28—H28A109.5F26—C80—C79116 (4)
C26—C28—H28B109.5F25—C80—C79110 (4)
H28A—C28—H28B109.5F27—C80—C79110 (3)
C26—C28—H28C109.4C82—C81—C79122 (4)
H28A—C28—H28C109.5C82—C81—H81119.1
H28B—C28—H28C109.5C79—C81—H81119.1
C26—C29—H29A109.4O10—C82—C81129 (4)
C26—C29—H29B109.5O10—C82—C83116 (4)
H29A—C29—H29B109.5C81—C82—C83115 (4)
C26—C29—H29C109.5F28—C83—F29108 (3)
H29A—C29—H29C109.5F28—C83—F30107 (3)
H29B—C29—H29C109.5F29—C83—F30106 (3)
C31—C30—C35118 (4)F28—C83—C82115 (4)
C31—C30—N4121 (4)F29—C83—C82109 (3)
C35—C30—N4121 (4)F30—C83—C82112 (3)
C30—C31—C32121 (4)O11—C84—C86130 (4)
C30—C31—H31119.4O11—C84—C85113 (4)
C32—C31—H31119.4C86—C84—C85117 (4)
C33—C32—C31121 (4)F32—C85—F31110 (4)
C33—C32—H32119.5F32—C85—F33107 (4)
C31—C32—H32119.5F31—C85—F33106 (4)
C34—C33—C32117 (4)F32—C85—C84111 (4)
C34—C33—C36122 (4)F31—C85—C84113 (4)
C32—C33—C36120 (4)F33—C85—C84110 (4)
C35—C34—C33123 (4)C84—C86—C87121 (4)
C35—C34—H34118.5C84—C86—H86119.6
C33—C34—H34118.6C87—C86—H86119.7
C34—C35—C30120 (4)O12—C87—C86125 (4)
C34—C35—H35120.2O12—C87—C88120 (4)
C30—C35—H35120.1C86—C87—C88115 (4)
C39—C36—C37108 (4)F35—C88—F34105 (3)
C39—C36—C38108 (4)F35—C88—F36101 (4)
C37—C36—C38109 (4)F34—C88—F3699 (4)
C39—C36—C33112 (3)F35—C88—C87114 (4)
C37—C36—C33111 (3)F34—C88—C87121 (4)
C38—C36—C33109 (3)F36—C88—C87114 (4)
C36—C37—H37A109.5C1S—O1S—C1Si180 (9)
C36—C37—H37B109.4C2S—C1S—O1S152 (10)
H37A—C37—H37B109.5
Symmetry code: (i) x, y, z+1.

Experimental details

Crystal data
Chemical formula[Zn(C29H35N3)2][Zn(C5HF6O2)3]2·0.5C4H10O
Mr2321.68
Crystal system, space groupMonoclinic, C2/c
Temperature (K)150
a, b, c (Å)42.138 (2), 19.4444 (10), 26.255 (2)
β (°) 110.969 (10)
V3)20088 (2)
Z8
Radiation typeMo Kα
µ (mm1)0.84
Crystal size (mm)0.35 × 0.22 × 0.22
Data collection
DiffractometerNonius FAST TV area-detector
diffractometer
Absorption correctionPart of the refinement model (ΔF)
(DIFABS; Walker & Stuart, 1983)
Tmin, Tmax0.758, 0.837
No. of measured, independent and
observed [I > 2σ(I)] reflections
26256, 14012, 6038
Rint0.074
(sin θ/λ)max1)0.598
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.061, 0.129, 0.76
No. of reflections14012
No. of parameters1348
No. of restraints30
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
(Δ/σ)max1.002
Δρmax, Δρmin (e Å3)1.04, 0.83

Computer programs: MADNES (Pflugrath & Messerschmidt, 1989), MADNES, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), PLATON (Spek, 1990).

Selected geometric parameters (Å, º) top
Zn1—N52.03 (3)Zn2—O52.07 (3)
Zn1—N22.06 (3)Zn2—O42.07 (3)
Zn1—N32.15 (3)Zn2—O62.13 (3)
Zn1—N42.19 (3)Zn3—O122.03 (3)
Zn1—N12.20 (3)Zn3—O82.06 (3)
Zn1—N62.31 (3)Zn3—O72.06 (3)
Zn2—O22.06 (3)Zn3—O112.07 (3)
Zn2—O32.06 (3)Zn3—O92.07 (3)
Zn2—O12.07 (3)Zn3—O102.10 (3)
N5—Zn1—N2165.2 (11)O1—Zn2—O4173.2 (11)
N5—Zn1—N3111.5 (11)O5—Zn2—O498.1 (11)
N2—Zn1—N375.4 (11)O2—Zn2—O698.8 (11)
N5—Zn1—N476.6 (11)O3—Zn2—O6160.3 (10)
N2—Zn1—N4116.6 (11)O1—Zn2—O694.8 (11)
N3—Zn1—N495.4 (11)O5—Zn2—O681.8 (10)
N5—Zn1—N199.2 (12)O4—Zn2—O681.5 (12)
N2—Zn1—N174.0 (11)O12—Zn3—O887.5 (11)
N3—Zn1—N1149.1 (12)O12—Zn3—O7175.3 (11)
N4—Zn1—N195.1 (11)O8—Zn3—O789.2 (11)
N5—Zn1—N673.9 (11)O12—Zn3—O1186.0 (11)
N2—Zn1—N692.9 (11)O8—Zn3—O1192.2 (11)
N3—Zn1—N694.1 (10)O7—Zn3—O1190.8 (11)
N4—Zn1—N6150.5 (11)O12—Zn3—O999.6 (11)
N1—Zn1—N690.9 (11)O8—Zn3—O9169.1 (11)
O2—Zn2—O395.7 (11)O7—Zn3—O984.0 (11)
O2—Zn2—O186.6 (11)O11—Zn3—O996.4 (11)
O3—Zn2—O199.3 (11)O12—Zn3—O1085.8 (11)
O2—Zn2—O5173.5 (11)O8—Zn3—O1087.1 (11)
O3—Zn2—O585.2 (11)O7—Zn3—O1097.4 (11)
O1—Zn2—O586.9 (11)O11—Zn3—O10171.8 (12)
O2—Zn2—O488.4 (11)O9—Zn3—O1085.3 (11)
O3—Zn2—O485.7 (11)
 

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