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metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 69| Part 2| February 2013| Pages m112-m113
doi:10.1107/S1600536813001396

(Aceto­nitrile){2-[bis­­(pyridin-2-ylmethyl-κ2N)amino-κN]-N-(2,6-di­methyl­phen­yl)acetamide-κO}(perchlorato-κO)zinc (aceto­nitrile){2-[bis­­(pyridin-2-ylmethyl-κ2N)amino-κN]-N-(2,6-di­methyl­phen­yl)acetamide-κO}zinc tris­­(perchlorate)

Ove Alexander Høgmoen Åstrand,a Carl Henrik Görbitz,b Kenneth Aase Kristoffersenb and Pål Rongveda*

aSchool of Pharmacy, University of Oslo, PO Box 1068 Blindern, N-0316 Oslo, Norway, and bDepartment of Chemistry, University of Oslo, PO Box 1033 Blindern, N-0315 Oslo, Norway
*Correspondence e-mail: pal.rongved@farmasi.uio.no

(Received 9 October 2012; accepted 14 January 2013; online 19 January 2013)

In the title salt, [Zn(C22H24N4O)(CH3CN)][Zn(ClO4)(C22H24N4O)(CH3CN)](ClO4)3, two differently coordinated zinc cations occur. In the first complex, the metal ion is coordinated by the N,N′,N′′,O-tetra­dentate acetamide ligand and an acetonitrile N atom, generating an approximate trigonal–bipyramidal coordination geometry, with the O atom in an equatorial site and the acetonitrile N atom in an axial site. In the second complex ion, a perchlorate ion is also bonded to the zinc ion, generating a distorted trans-ZnO2N4 octa­hedron. Of the uncoordinating perchlorate ions, one lies on a crystallographic twofold axis and one lies close to a twofold axis and has a site occupancy of 0.5. N—H⋯O and N—H⋯(O,O) hydrogen bonds are observed in the crystal. Disordered solvent mol­ecules occupy about 11% of the unit-cell volume; their contribution to the scattering was removed with the SQUEEZE routine of the PLATON program [Spek (2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]). Acta Cryst. D65, 148–155.].

Related literature

For related structures found in the Cambridge Structural Database (Version 5.33 of November 2011; Allen, 2002[Allen, F. H. (2002). Acta Cryst. B58, 380-388.]), see: Xu et al. (2010a[Xu, Z., Baek, K.-H., Kim, H. N., Cui, J., Qian, X., Spring, D. R., Shin, I. & Yoon, J. (2010a). J. Am. Chem. Soc. 132, 601-610.],b[Xu, Z., Han, S. J., Lee, C., Yoon, J. & Spring, D. R. (2010b). Chem. Commun. 46, 1679-1682.]); Patten et al. (2008[Patten, T. E., Olmstead, M. M. & Troeltzsch, C. (2008). Inorg. Chim. Acta, 361, 365-372.]); Marlin et al. (2006[Marlin, D. S., Cabrera, D. G., Leigh, D. A. & Slawin, A. M. Z. (2006). Angew. Chem. Int. Ed. 45, 77-83.]). For biochemical background, see: Makhov et al. (2008[Makhov, P., Golovine, K., Uzzo, R. G., Rothman, J., Crispen, P. L., Shaw, T., Scoll, B. J. & Kolenko, V. M. (2008). Cell Death Differ. 15, 1745-1751.]); Xu et al. (2010a[Xu, Z., Baek, K.-H., Kim, H. N., Cui, J., Qian, X., Spring, D. R., Shin, I. & Yoon, J. (2010a). J. Am. Chem. Soc. 132, 601-610.]).

[Scheme 1]

Experimental

Crystal data

  • [Zn(C22H24N4O)(C2H3N)][Zn(ClO4)(C22H24N4O)(C2H3N)](ClO4)3

  • Mr = 1331.59

  • Monoclinic, C 2/c

  • a = 41.253 (8) Å

  • b = 15.057 (3) Å

  • c = 20.809 (4) Å

  • β = 106.106 (2)°

  • V = 12418 (4) Å3

  • Z = 8

  • Mo Kα radiation

  • μ = 1.03 mm−1

  • T = 105 K

  • 0.91 × 0.29 × 0.22 mm
Data collection

  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2007[Bruker (2007). APEX2, SAINT-Plus and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.531, Tmax = 0.798

  • 43906 measured reflections

  • 10987 independent reflections

  • 8503 reflections with I > 2σ(I)

  • Rint = 0.051
Refinement

  • R[F2 > 2σ(F2)] = 0.045

  • wR(F2) = 0.124

  • S = 1.07

  • 10987 reflections

  • 782 parameters

  • 8 restraints

  • H-atom parameters constrained

  • Δρmax = 0.89 e Å−3

  • Δρmin = −0.66 e Å−3

Table 1
Selected bond lengths (Å)

Zn1A—N4A 2.058 (3)
Zn1A—N3A 2.059 (3)
Zn1A—N5A 2.060 (3)
Zn1A—O1A 2.087 (2)
Zn1A—N2A 2.236 (2)
Zn1A—O1D 2.310 (2)
Zn1B—N3B 2.020 (3)
Zn1B—O1B 2.025 (2)
Zn1B—N4B 2.040 (3)
Zn1B—N5B 2.043 (3)
Zn1B—N2B 2.240 (2)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
N1A—H1A⋯O3Di 0.88 2.00 2.868 (3) 171
N1B—H1B⋯O4Eii 0.88 2.15 2.979 (3) 157
N1B—H1B⋯O3Eii 0.88 2.41 3.138 (4) 141
Symmetry codes: (i) [x, -y+1, z+{\script{1\over 2}}]; (ii) [x, -y, z+{\script{1\over 2}}].

Data collection: APEX2 (Bruker, 2007[Bruker (2007). APEX2, SAINT-Plus and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT-Plus (Bruker, 2007[Bruker (2007). APEX2, SAINT-Plus and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL and Mercury (Macrae et al., 2008[Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.]); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536813001396/hb6972sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813001396/hb6972Isup2.hkl

checkCIF report


Comment top

The title compound (I) was prepared as part of a series of zinc-binding ligands to be tested biologically. Zinc chelation may induce apoptosis in prostate cancer cells (Makhov et al., 2008), and may be used as Zn2+-selective, cell-permeable, and ratiometric fluorescent sensors (Xu et al., 2010a) for biological mapping of disease. The title compound was synthesized from 2,6-dimethyl aniline, chloroacetyl chloride and N,N'-dipicolylamine in a two-step procedure as a part of a larger work that will be published in due time.

The asymmetric unit is shown in Fig. 1 (a). Two independent 2-[bis(pyridin-2-ylmethyl)amino]-N-(2,6-dimethylphenyl) acetamides A and B act as tetradentate ligands for Zn2+ ions. Cocrystallized acetonitrile solvent molecules serve as additional ligands. There are five different perchlorate anions C, D, E, F and G, the latter two being located on (F) or very close to (G) a twofold axis. Perchlorate D serves as ligand number six for Zn1A, Fig. 1 (b), while perchlorate E is only loosely connected to Zn1B, Fig. 1(c). This means that Zn1A is octahedrally coordinated, while Zn1B has distorted trigonal bipyramidal geometry, Fig. 2. The effect on the overall molecular geometries is evident from the overlay in Fig. 3, which yields a RMS deviation of 0.76 Å. Torsion angle deviations between the two complexes are usually in the range 0 – 20°, but reaches 68.5° for C17—N2—C11—C12 [A: -85.1 (3)°; B: -153.6 (3)°]. The unit cell and crystal packing arrangement are shown in Fig. 4. Non-identical complexes are stacked on top of each other along the b axis. Perchlorate C sits between the A and B complexes and is involved in six C—H···O interactions with H···O distance < 2.7 Å, five out of which have >CH2 donors. The perchlorate ions F and G interact primarily with unidentified disordered solvent molecules inside large, but isolated pockets. Amide H-atoms on N1A and N1B are donated to perchlorate ion D and E, respectively, to give one normal hydrogen bond and one three-centre hydrogen bond as listed in Table 1.

There are five other structures with a similar hydrocarbon skeleton in the Cambridge Structural Database (version 5.33 of November 2011; Allen 2002) with refcodes CECDOE (Marlin et al., 2006), CECDUK (Marlin et al., 2006), GUQRUG (Xu et al., 2010b) XIXWAD (Patten et al., 2008) and YUTTEN (Xu et al., 2010a). In four complexes the substituted N-phenylacetamide acts as a tetradentate ligand for a metal ion (the fifth is CECDOE where the amid carbonyl group is not coordinated), but the total coordination number is always five. YUTTEN is chemically very similar to I; the metal ion is Zn2+ with acetonitrile as an additional ligand, only the two methyl groups on the N-phenyl ring are missing. The molecular conformation is almost identical to molecule I B except for a slightly different orientation for the N-phenyl group.

Related literature top

For related structures found in the Cambridge Structural Database (Version 5.33 of November 2011; Allen, 2002), see: Xu et al. (2010a,b); Patten et al. (2008); Marlin et al. (2006). For biochemical background, see: Makhov et al. (2008); Xu et al. (2010a).

Experimental top

Colourless needles of (I) were obtained by dissolving 50 mg of a 1:1 mixture of the ligand and zinc perchlorate in 1 ml dry acetonitrile and transferring 0.5 ml into a 1.5 ml vial which was capped and a pinhole (0.5 mm) made in the cap. This was placed in a 5 ml vial with diethyl ether to allow slow evaporation of ether into the acetonitrile solution. After approximately 48 h at 4 °C, clear crystals appeared.

Refinement top

H atoms were positioned with idealized geometry and fixed C/N—H distances for NH, CH3, CH2 and CH (sp2) at 0.88, 0.98, 0.99 and 0.95 Å, respectively. Two perchlorate anions are located on (F) or close to (G) a twofold rotation axis, and associated atoms have an occupancy of 0.5. Furthermore, displacement ellipsoids for O atoms are large, making an unrestrained refinement difficult. Cl—O distances were thus restrained to be close to 1.43 Å through SHELX DFIX 1.430 0.005 commands. Electron density in the solvent regions of the crystal were initially modelled by 8 - 10 partially occupied oxygen atoms, but this proved not to be satisfactory. The electron density was consequently synthetically removed by the SQEEZE routine of the PLATON program (Spek, 2009), yielding a significant improvement for R(F) as well as wR(F2).

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT-Plus (Bruker, 2007); data reduction: SAINT-Plus (Bruker, 2007); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008) and Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. (a) The asymmetric unit with H atoms omitted for clarity. C atoms in molecule A (including the associated acetonitrile ligand) are shown in light grey colour, as opposed to C atoms in molecule B which are dark grey. O atoms in perchlorate ion D, coordinating to molecule A, appear in orange, while O atoms in perchlorate ion E close to B are dark red. Perchlorate ions F and G are depicted here as light green and green spheres, respectively, to reduce overlap with A and B. (b) Complex A with perchlorate D. One pyridine ring has been shaded. (c) Complex B with perchlorate E. The indicated distances are Zn1B···O1E = 3.077 (3) Å and Zn1B···O2E = 3.827 (3) Å, which may be compared to 2.310 (3) Å for O1D-Zn1A. Displacement ellipsoids in (b) and (c) are shown at the 50% probability level with H atoms as spheres of arbitrary size.
[Figure 2] Fig. 2. Octahedral geometry at Zn1A (left) and trigonal bipyramidal geometry at Zn1B (right). In-plane bond angles (°) have been indicated. N3—Zn1—N4 undergoes an opening of 27.4° from B to A to accommodate the extra perchlorate ligand O1D. In both complexes the N5—Zn1—N3/N4/O1 angles are slightly larger than the N2—Zn1—N3/N4/O1 angles, with ranges 96.0 - 102.8° and 78.7 - 80.3°, respectively.
[Figure 3] Fig. 3. Stereo view of a molecular overlap between complex A and complex B. Colour coding as in Fig. 1(a), except that for molecule A N and O atoms are shown in lighter colours. The dashed arrow indicates the position of perchlorate D coordinating to A, which mainly serves to push the shaded ring system [see Fig. 1(b)] to the left.
[Figure 4] Fig. 4. Molecular packing viewed along the b axis. Colour coding as in Fig. 1(a). The 'Display Voids' tool in Mercury (Macrae et al., 2008), with a 1.2 Å probe radius and 0.4 Å grid spacing, has been used to highlight regions of disordered solvent accounting for about 11% of the unit cell volume.
(Acetonitrile){2-[bis(pyridin-2-ylmethyl-κ2N)amino-κN]- N-(2,6-dimethylphenyl)acetamide-κO}(perchlorato-κO)zinc (acetonitrile){2-[bis(pyridin-2-ylmethyl-κ2N)amino-κN]- N-(2,6-dimethylphenyl)acetamide-κO}zinc tris(perchlorate) top
Crystal data top
[Zn(C22H24N4O)(C2H3N)][Zn(ClO4)(C22H24N4O)(C2H3N)](ClO4)3F(000) = 5716
Mr = 1331.59Dx = 1.490 Mg m−3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 8118 reflections
a = 41.253 (8) Åθ = 2.4–25.0°
b = 15.057 (3) ŵ = 1.03 mm−1
c = 20.809 (4) ÅT = 105 K
β = 106.106 (2)°Needle, colourless
V = 12418 (4) Å30.91 × 0.29 × 0.22 mm
Z = 8
Data collection top
Bruker APEXII CCD
diffractometer		10987 independent reflections
Radiation source: fine-focus sealed tube8503 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.051
Detector resolution: 8.3 pixels mm-1θmax = 25.1°, θmin = 1.7°
Sets of exposures each taken over 0.5° ω rotation scansh = −44→49
Absorption correction: multi-scan
(SADABS; Bruker, 2007)		k = −17→17
Tmin = 0.531, Tmax = 0.798l = −24→24
43906 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.045Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.124H-atom parameters constrained
S = 1.07 w = 1/[σ2(Fo2) + (0.0725P)2 + 5.6036P]
where P = (Fo2 + 2Fc2)/3
10987 reflections(Δ/σ)max = 0.002
782 parametersΔρmax = 0.89 e Å−3
8 restraintsΔρmin = −0.66 e Å−3
Crystal data top
[Zn(C22H24N4O)(C2H3N)][Zn(ClO4)(C22H24N4O)(C2H3N)](ClO4)3V = 12418 (4) Å3
Mr = 1331.59Z = 8
Monoclinic, C2/cMo Kα radiation
a = 41.253 (8) ŵ = 1.03 mm−1
b = 15.057 (3) ÅT = 105 K
c = 20.809 (4) Å0.91 × 0.29 × 0.22 mm
β = 106.106 (2)°
Data collection top
Bruker APEXII CCD
diffractometer		10987 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2007)		8503 reflections with I > 2σ(I)
Tmin = 0.531, Tmax = 0.798Rint = 0.051
43906 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0458 restraints
wR(F2) = 0.124H-atom parameters constrained
S = 1.07Δρmax = 0.89 e Å−3
10987 reflectionsΔρmin = −0.66 e Å−3
782 parameters
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.

Refinement. Refinement of F2 against ALL reflections. Electron density from disordered solvent removed by the PLATON SQUEEZE routine. Total void volume is approximately 11% of the unit cell volume.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
Zn1A0.853323 (9)0.59127 (2)0.162884 (16)0.02556 (11)
O1A0.86383 (6)0.64960 (14)0.25739 (10)0.0357 (6)
N1A0.85940 (7)0.63530 (18)0.36241 (13)0.0351 (7)
H1A0.85030.60550.38940.042*
N2A0.82241 (7)0.50432 (18)0.21004 (12)0.0319 (6)
N3A0.80643 (7)0.64892 (18)0.12842 (12)0.0301 (6)
N4A0.88783 (7)0.49269 (16)0.20125 (11)0.0277 (6)
N5A0.88304 (7)0.67580 (17)0.12576 (12)0.0279 (6)
C1A0.88254 (10)0.7057 (2)0.39009 (15)0.0391 (9)
C2A0.86923 (10)0.7820 (2)0.41226 (15)0.0411 (9)
C3A0.89170 (12)0.8510 (3)0.43869 (17)0.0525 (11)
H3A0.88360.90360.45420.063*
C4A0.92540 (13)0.8436 (3)0.44246 (19)0.0620 (13)
H4A0.94020.89130.46020.074*
C5A0.93797 (12)0.7677 (3)0.42077 (19)0.0594 (12)
H5A0.96140.76370.42410.071*
C6A0.91669 (11)0.6969 (3)0.39398 (18)0.0484 (10)
C7A0.83236 (10)0.7897 (2)0.40674 (17)0.0465 (10)
H71A0.82790.84700.42510.070*
H72A0.82560.74140.43190.070*
H73A0.81940.78580.35960.070*
C8A0.93093 (11)0.6146 (3)0.3702 (2)0.0627 (13)
H81A0.91270.57220.35210.094*
H82A0.94770.58740.40790.094*
H83A0.94160.63090.33530.094*
C9A0.85096 (9)0.6129 (2)0.29855 (15)0.0322 (8)
C10A0.82307 (9)0.5447 (2)0.27544 (16)0.0363 (8)
H10A0.82620.49720.30950.044*
H9A0.80110.57360.27180.044*
C11A0.78842 (9)0.5068 (2)0.16266 (16)0.0394 (9)
H11A0.77150.48910.18590.047*
H12A0.78720.46400.12600.047*
C12A0.78053 (9)0.5981 (2)0.13426 (16)0.0360 (8)
C13A0.80065 (9)0.7317 (2)0.10342 (15)0.0358 (8)
H13A0.81920.76680.09970.043*
C14A0.76876 (10)0.7668 (3)0.08320 (17)0.0482 (10)
H14A0.76520.82590.06690.058*
C15A0.74182 (11)0.7138 (3)0.08713 (19)0.0599 (12)
H15A0.71940.73560.07200.072*
C16A0.74785 (10)0.6298 (3)0.11291 (18)0.0512 (10)
H16A0.72960.59330.11610.061*
C17A0.83855 (9)0.4168 (2)0.21700 (16)0.0343 (8)
H17A0.82880.38190.17580.041*
H18A0.83360.38480.25480.041*
C18A0.87640 (9)0.4226 (2)0.22913 (15)0.0314 (8)
C19A0.92118 (8)0.4992 (2)0.20791 (15)0.0300 (7)
H19A0.92930.54860.18860.036*
C20A0.94391 (10)0.4368 (2)0.24175 (17)0.0407 (9)
H20A0.96730.44300.24540.049*
C21A0.93244 (11)0.3651 (2)0.27029 (18)0.0458 (10)
H21A0.94770.32100.29360.055*
C22A0.89839 (11)0.3586 (2)0.26436 (16)0.0410 (9)
H22A0.89000.31030.28440.049*
C23A0.90154 (8)0.7206 (2)0.11036 (14)0.0298 (7)
C24A0.92560 (10)0.7789 (3)0.09111 (17)0.0472 (10)
H24A0.91930.84100.09510.071*
H25A0.92530.76670.04470.071*
H26A0.94830.76820.12060.071*
Zn1B0.850909 (9)0.10724 (2)0.182215 (16)0.02359 (11)
O1B0.86112 (5)0.16804 (13)0.27244 (9)0.0280 (5)
N1B0.86223 (7)0.15562 (16)0.38094 (12)0.0285 (6)
H1B0.85300.13120.41010.034*
N2B0.81877 (7)0.02712 (17)0.23148 (12)0.0283 (6)
N3B0.80573 (7)0.12094 (17)0.11358 (12)0.0266 (6)
N4B0.88036 (7)−0.00293 (17)0.20878 (11)0.0295 (6)
N5B0.88183 (7)0.18507 (17)0.14441 (12)0.0298 (6)
C1B0.88784 (9)0.2221 (2)0.40386 (14)0.0303 (7)
C2B0.87858 (9)0.3043 (2)0.42471 (15)0.0331 (8)
C3B0.90378 (11)0.3676 (3)0.44669 (19)0.0480 (10)
H3B0.89830.42400.46130.058*
C4B0.93672 (11)0.3495 (3)0.4476 (2)0.0628 (14)
H4B0.95360.39380.46210.075*
C5B0.94530 (10)0.2678 (3)0.42749 (18)0.0554 (12)
H5B0.96810.25600.42910.066*
C6B0.92113 (9)0.2023 (2)0.40488 (16)0.0389 (8)
C7B0.84309 (9)0.3234 (2)0.42462 (16)0.0396 (8)
H71B0.84160.38390.44090.059*
H72B0.83610.28100.45390.059*
H73B0.82830.31770.37900.059*
C8B0.93100 (11)0.1128 (3)0.3822 (2)0.0536 (11)
H81B0.91090.07500.36770.080*
H82B0.94760.08420.41930.080*
H83B0.94080.12150.34470.080*
C9B0.85185 (8)0.12953 (19)0.31777 (14)0.0264 (7)
C10B0.82974 (9)0.0476 (2)0.30370 (14)0.0336 (8)
H10B0.8424−0.00360.32830.040*
H9B0.80960.05730.32000.040*
C11B0.78361 (9)0.0504 (2)0.19832 (16)0.0355 (8)
H11B0.77620.09730.22450.043*
H12B0.7692−0.00230.19740.043*
C12B0.77897 (8)0.0831 (2)0.12761 (15)0.0304 (7)
C13B0.80221 (9)0.1555 (2)0.05235 (14)0.0305 (7)
H13B0.82120.18190.04270.037*
C14B0.77192 (9)0.1537 (2)0.00329 (16)0.0392 (8)
H14B0.76990.1788−0.03950.047*
C15B0.74445 (9)0.1144 (3)0.01802 (18)0.0443 (9)
H15B0.72320.1120−0.01480.053*
C16B0.74821 (9)0.0789 (2)0.08056 (17)0.0401 (9)
H16B0.72960.05150.09110.048*
C17B0.82742 (9)−0.0648 (2)0.21670 (15)0.0341 (8)
H17B0.8152−0.08010.17000.041*
H18B0.8203−0.10680.24670.041*
C18B0.86462 (10)−0.0734 (2)0.22624 (14)0.0347 (8)
C19B0.91337 (9)−0.0069 (2)0.21427 (15)0.0383 (8)
H19B0.92410.04310.20120.046*
C20B0.93232 (12)−0.0811 (3)0.23819 (19)0.0541 (11)
H20B0.9558−0.08190.24240.065*
C21B0.91691 (13)−0.1536 (3)0.25579 (19)0.0604 (13)
H21B0.9295−0.20570.27170.072*
C22B0.88279 (13)−0.1505 (2)0.25024 (17)0.0515 (11)
H22B0.8718−0.20040.26260.062*
C23B0.90020 (8)0.2236 (2)0.12319 (15)0.0281 (7)
C24B0.92369 (9)0.2734 (2)0.09660 (17)0.0398 (8)
H24B0.91970.33720.10000.060*
H25B0.92040.25750.04960.060*
H26B0.94690.25930.12220.060*
Cl1C0.75770 (2)0.28630 (6)0.23363 (4)0.0396 (2)
O1C0.75333 (10)0.3701 (2)0.25924 (17)0.0862 (12)
O2C0.78840 (7)0.24711 (19)0.27441 (14)0.0571 (7)
O3C0.73026 (8)0.2301 (2)0.23552 (16)0.0809 (11)
O4C0.76038 (7)0.29391 (18)0.16670 (12)0.0530 (7)
Cl1D0.850080 (19)0.44683 (5)0.03225 (3)0.02583 (17)
O1D0.83426 (6)0.51464 (14)0.06334 (10)0.0336 (5)
O2D0.88496 (6)0.46675 (16)0.04288 (11)0.0383 (6)
O3D0.83300 (6)0.44678 (15)−0.03836 (10)0.0338 (5)
O4D0.84614 (6)0.36250 (15)0.06091 (11)0.0381 (6)
Cl1E0.83903 (2)−0.05427 (5)0.02203 (4)0.0377 (2)
O1E0.86080 (8)0.0128 (2)0.05791 (13)0.0635 (8)
O2E0.80982 (8)−0.06216 (17)0.04704 (13)0.0554 (8)
O3E0.85568 (9)−0.13788 (19)0.02709 (15)0.0730 (10)
O4E0.82850 (6)−0.02999 (15)−0.04755 (10)0.0376 (6)
Cl1F1.00000.70818 (12)0.25000.0630 (4)
O1F0.99954 (17)0.7857 (4)0.2109 (4)0.091 (3)0.50
O2F0.9785 (3)0.6454 (9)0.2089 (7)0.201 (9)0.50
O3F0.9906 (3)0.7262 (9)0.3106 (4)0.169 (6)0.50
O4F1.03261 (14)0.6715 (6)0.2706 (4)0.0487 (17)0.50
Cl1G0.9993 (2)0.18690 (15)0.2590 (3)0.0619 (13)0.50
O1G0.9975 (2)0.2081 (7)0.3251 (3)0.099 (3)0.50
O2G0.9977 (2)0.2677 (5)0.2198 (4)0.102 (3)0.50
O3G1.0325 (2)0.1570 (7)0.2653 (4)0.058 (2)0.50
O4G0.9744 (4)0.1271 (10)0.2236 (9)0.177 (9)0.50
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Zn1A0.0336 (2)0.0267 (2)0.02145 (19)−0.00585 (15)0.01601 (15)−0.00028 (13)
O1A0.0585 (16)0.0321 (12)0.0247 (11)−0.0157 (11)0.0252 (11)−0.0058 (9)
N1A0.0521 (19)0.0370 (16)0.0237 (14)−0.0075 (13)0.0230 (13)−0.0007 (11)
N2A0.0405 (17)0.0357 (15)0.0262 (13)−0.0123 (13)0.0205 (12)−0.0069 (11)
N3A0.0319 (16)0.0360 (16)0.0268 (14)−0.0038 (12)0.0155 (12)−0.0065 (11)
N4A0.0405 (17)0.0247 (13)0.0204 (12)−0.0064 (12)0.0124 (11)0.0003 (10)
N5A0.0360 (16)0.0282 (14)0.0220 (13)−0.0023 (12)0.0123 (12)0.0038 (10)
C1A0.059 (3)0.045 (2)0.0185 (15)−0.0104 (18)0.0196 (16)−0.0038 (14)
C2A0.064 (3)0.043 (2)0.0184 (15)−0.0044 (18)0.0158 (16)−0.0033 (14)
C3A0.080 (3)0.050 (2)0.0283 (19)−0.011 (2)0.017 (2)−0.0108 (16)
C4A0.084 (4)0.066 (3)0.037 (2)−0.032 (3)0.018 (2)−0.021 (2)
C5A0.068 (3)0.077 (3)0.039 (2)−0.024 (2)0.024 (2)−0.022 (2)
C6A0.066 (3)0.053 (2)0.0343 (19)−0.014 (2)0.0269 (19)−0.0153 (17)
C7A0.069 (3)0.043 (2)0.0305 (18)0.0051 (19)0.0178 (18)−0.0040 (15)
C8A0.055 (3)0.083 (3)0.060 (3)−0.012 (2)0.033 (2)−0.032 (2)
C9A0.047 (2)0.0301 (17)0.0269 (17)−0.0046 (15)0.0227 (15)−0.0010 (13)
C10A0.056 (2)0.0345 (18)0.0282 (17)−0.0119 (17)0.0275 (16)−0.0047 (14)
C11A0.042 (2)0.049 (2)0.0333 (18)−0.0195 (17)0.0201 (16)−0.0115 (15)
C12A0.033 (2)0.056 (2)0.0238 (16)−0.0071 (17)0.0162 (14)−0.0118 (15)
C13A0.039 (2)0.045 (2)0.0258 (16)0.0003 (16)0.0148 (15)−0.0082 (14)
C14A0.051 (3)0.070 (3)0.0244 (18)0.015 (2)0.0121 (17)−0.0015 (17)
C15A0.036 (2)0.108 (4)0.038 (2)0.015 (2)0.0150 (18)0.006 (2)
C16A0.042 (2)0.085 (3)0.0302 (19)−0.007 (2)0.0166 (17)0.0027 (19)
C17A0.053 (2)0.0292 (17)0.0286 (17)−0.0150 (16)0.0246 (16)−0.0050 (13)
C18A0.055 (2)0.0224 (16)0.0210 (15)−0.0104 (15)0.0178 (15)−0.0039 (12)
C19A0.036 (2)0.0290 (17)0.0273 (16)−0.0044 (14)0.0123 (14)0.0012 (13)
C20A0.044 (2)0.043 (2)0.0370 (19)0.0028 (17)0.0141 (17)0.0000 (15)
C21A0.063 (3)0.035 (2)0.039 (2)0.0108 (18)0.0149 (19)0.0054 (16)
C22A0.077 (3)0.0217 (17)0.0294 (18)−0.0029 (17)0.0233 (18)0.0018 (13)
C23A0.035 (2)0.0377 (18)0.0165 (14)−0.0063 (15)0.0070 (13)0.0032 (12)
C24A0.050 (2)0.063 (3)0.0301 (18)−0.027 (2)0.0136 (17)0.0120 (17)
Zn1B0.0323 (2)0.02355 (19)0.01785 (18)−0.00281 (15)0.01191 (15)0.00170 (13)
O1B0.0390 (13)0.0292 (12)0.0199 (10)−0.0083 (10)0.0148 (9)−0.0004 (8)
N1B0.0420 (17)0.0286 (14)0.0200 (12)−0.0082 (12)0.0171 (12)−0.0026 (10)
N2B0.0417 (17)0.0279 (14)0.0186 (12)−0.0111 (12)0.0140 (11)−0.0053 (10)
N3B0.0317 (16)0.0276 (13)0.0244 (13)−0.0009 (11)0.0140 (11)−0.0030 (10)
N4B0.0459 (18)0.0264 (14)0.0195 (12)0.0023 (12)0.0143 (12)0.0006 (10)
N5B0.0361 (17)0.0309 (14)0.0248 (13)−0.0018 (13)0.0126 (12)0.0026 (11)
C1B0.041 (2)0.0364 (18)0.0170 (14)−0.0105 (15)0.0134 (13)−0.0042 (12)
C2B0.048 (2)0.0337 (18)0.0227 (15)−0.0107 (16)0.0191 (15)−0.0046 (13)
C3B0.067 (3)0.043 (2)0.045 (2)−0.023 (2)0.033 (2)−0.0189 (17)
C4B0.059 (3)0.086 (3)0.056 (3)−0.043 (2)0.037 (2)−0.039 (2)
C5B0.043 (2)0.092 (3)0.038 (2)−0.022 (2)0.0228 (18)−0.029 (2)
C6B0.042 (2)0.053 (2)0.0247 (16)−0.0063 (18)0.0153 (15)−0.0099 (15)
C7B0.054 (2)0.0364 (19)0.0300 (18)−0.0040 (17)0.0149 (16)−0.0051 (14)
C8B0.050 (3)0.068 (3)0.043 (2)0.008 (2)0.0126 (19)−0.0159 (19)
C9B0.0375 (19)0.0229 (15)0.0231 (15)−0.0012 (13)0.0157 (14)−0.0019 (12)
C10B0.055 (2)0.0329 (18)0.0181 (15)−0.0144 (16)0.0191 (15)−0.0053 (12)
C11B0.041 (2)0.040 (2)0.0337 (18)−0.0138 (16)0.0234 (16)−0.0060 (14)
C12B0.0316 (19)0.0346 (18)0.0289 (17)−0.0041 (14)0.0148 (14)−0.0095 (13)
C13B0.038 (2)0.0323 (18)0.0237 (16)0.0019 (14)0.0118 (14)0.0011 (13)
C14B0.042 (2)0.049 (2)0.0258 (17)0.0093 (17)0.0066 (15)0.0006 (15)
C15B0.030 (2)0.062 (3)0.037 (2)0.0012 (18)0.0034 (16)−0.0092 (17)
C16B0.034 (2)0.052 (2)0.038 (2)−0.0043 (17)0.0157 (16)−0.0107 (16)
C17B0.062 (3)0.0224 (16)0.0216 (16)−0.0105 (15)0.0183 (16)−0.0029 (12)
C18B0.068 (3)0.0233 (16)0.0142 (14)−0.0010 (16)0.0135 (15)−0.0031 (12)
C19B0.050 (2)0.040 (2)0.0276 (17)0.0092 (17)0.0155 (16)−0.0012 (14)
C20B0.072 (3)0.054 (3)0.041 (2)0.031 (2)0.023 (2)0.0041 (18)
C21B0.100 (4)0.049 (3)0.036 (2)0.037 (3)0.025 (2)0.0056 (18)
C22B0.105 (4)0.0265 (19)0.0273 (18)0.008 (2)0.025 (2)0.0015 (14)
C23B0.0345 (19)0.0276 (17)0.0240 (15)0.0004 (14)0.0112 (14)0.0011 (12)
C24B0.040 (2)0.048 (2)0.0365 (19)−0.0099 (17)0.0182 (16)0.0063 (15)
Cl1C0.0416 (5)0.0407 (5)0.0386 (5)−0.0035 (4)0.0145 (4)0.0062 (4)
O1C0.147 (4)0.0483 (19)0.095 (3)0.0210 (19)0.086 (3)0.0033 (16)
O2C0.0470 (17)0.0647 (19)0.0505 (16)0.0011 (14)−0.0019 (13)0.0012 (14)
O3C0.0491 (19)0.109 (3)0.074 (2)−0.0276 (18)−0.0015 (16)0.0512 (19)
O4C0.0686 (19)0.0579 (17)0.0348 (14)−0.0013 (14)0.0182 (13)0.0032 (12)
Cl1D0.0305 (4)0.0283 (4)0.0233 (4)−0.0013 (3)0.0151 (3)−0.0022 (3)
O1D0.0405 (14)0.0354 (13)0.0281 (11)0.0048 (10)0.0151 (10)−0.0096 (9)
O2D0.0308 (14)0.0494 (15)0.0392 (13)−0.0029 (11)0.0174 (11)0.0063 (11)
O3D0.0397 (14)0.0441 (14)0.0208 (11)0.0025 (11)0.0138 (10)−0.0056 (9)
O4D0.0473 (16)0.0306 (12)0.0406 (13)−0.0016 (11)0.0191 (11)0.0043 (10)
Cl1E0.0660 (6)0.0328 (4)0.0176 (4)0.0110 (4)0.0173 (4)0.0008 (3)
O1E0.075 (2)0.076 (2)0.0349 (15)−0.0066 (17)0.0065 (14)−0.0191 (14)
O2E0.097 (2)0.0415 (15)0.0466 (15)0.0042 (15)0.0510 (16)−0.0005 (12)
O3E0.116 (3)0.0520 (18)0.0602 (19)0.0424 (18)0.0406 (19)0.0181 (14)
O4E0.0511 (16)0.0474 (14)0.0159 (10)0.0017 (12)0.0122 (10)0.0028 (9)
Cl1F0.0300 (8)0.0834 (12)0.0714 (10)0.0000.0072 (7)0.000
O1F0.048 (4)0.065 (4)0.136 (7)−0.019 (4)−0.012 (5)0.066 (4)
O2F0.128 (11)0.200 (17)0.201 (17)−0.126 (12)−0.077 (10)0.096 (12)
O3F0.164 (11)0.202 (13)0.201 (12)0.081 (10)0.150 (10)0.073 (10)
O4F0.034 (4)0.062 (4)0.049 (3)0.014 (3)0.011 (3)−0.003 (3)
Cl1G0.0392 (11)0.0748 (12)0.076 (4)−0.012 (2)0.024 (2)−0.030 (2)
O1G0.088 (6)0.144 (8)0.080 (5)0.025 (5)0.047 (4)−0.008 (5)
O2G0.077 (5)0.081 (5)0.155 (10)−0.002 (5)0.043 (8)0.048 (5)
O3G0.046 (5)0.078 (6)0.051 (4)0.018 (4)0.016 (3)−0.002 (3)
O4G0.103 (11)0.122 (12)0.262 (19)−0.064 (10)−0.020 (10)−0.007 (10)
Geometric parameters (Å, º) top
Zn1A—N4A2.058 (3)N2B—C10B1.477 (4)
Zn1A—N3A2.059 (3)N2B—C17B1.483 (4)
Zn1A—N5A2.060 (3)N3B—C12B1.344 (4)
Zn1A—O1A2.087 (2)N3B—C13B1.346 (4)
Zn1A—N2A2.236 (2)N4B—C19B1.336 (4)
Zn1A—O1D2.310 (2)N4B—C18B1.346 (4)
O1A—C9A1.254 (4)N5B—C23B1.137 (4)
N1A—C9A1.321 (4)C1B—C6B1.400 (5)
N1A—C1A1.435 (4)C1B—C2B1.400 (4)
N1A—H1A0.8800C2B—C3B1.391 (5)
N2A—C17A1.466 (4)C2B—C7B1.492 (5)
N2A—C11A1.474 (4)C3B—C4B1.381 (6)
N2A—C10A1.484 (4)C3B—H3B0.9500
N3A—C13A1.346 (4)C4B—C5B1.377 (6)
N3A—C12A1.347 (4)C4B—H4B0.9500
N4A—C19A1.347 (4)C5B—C6B1.388 (5)
N4A—C18A1.351 (4)C5B—H5B0.9500
N5A—C23A1.129 (4)C6B—C8B1.521 (5)
C1A—C6A1.395 (5)C7B—H71B0.9800
C1A—C2A1.406 (5)C7B—H72B0.9800
C2A—C3A1.399 (5)C7B—H73B0.9800
C2A—C7A1.498 (5)C8B—H81B0.9800
C3A—C4A1.375 (6)C8B—H82B0.9800
C3A—H3A0.9500C8B—H83B0.9800
C4A—C5A1.381 (6)C9B—C10B1.513 (4)
C4A—H4A0.9500C10B—H10B0.9900
C5A—C6A1.396 (5)C10B—H9B0.9900
C5A—H5A0.9500C11B—C12B1.513 (4)
C6A—C8A1.512 (6)C11B—H11B0.9900
C7A—H71A0.9800C11B—H12B0.9900
C7A—H72A0.9800C12B—C16B1.372 (5)
C7A—H73A0.9800C13B—C14B1.377 (5)
C8A—H81A0.9800C13B—H13B0.9500
C8A—H82A0.9800C14B—C15B1.386 (5)
C8A—H83A0.9800C14B—H14B0.9500
C9A—C10A1.517 (5)C15B—C16B1.376 (5)
C10A—H10A0.9900C15B—H15B0.9500
C10A—H9A0.9900C16B—H16B0.9500
C11A—C12A1.496 (5)C17B—C18B1.497 (5)
C11A—H11A0.9900C17B—H17B0.9900
C11A—H12A0.9900C17B—H18B0.9900
C12A—C16A1.382 (5)C18B—C22B1.396 (5)
C13A—C14A1.371 (5)C19B—C20B1.375 (5)
C13A—H13A0.9500C19B—H19B0.9500
C14A—C15A1.389 (6)C20B—C21B1.363 (6)
C14A—H14A0.9500C20B—H20B0.9500
C15A—C16A1.369 (6)C21B—C22B1.381 (6)
C15A—H15A0.9500C21B—H21B0.9500
C16A—H16A0.9500C22B—H22B0.9500
C17A—C18A1.514 (5)C23B—C24B1.451 (4)
C17A—H17A0.9900C24B—H24B0.9800
C17A—H18A0.9900C24B—H25B0.9800
C18A—C22A1.386 (5)C24B—H26B0.9800
C19A—C20A1.376 (5)Cl1C—O1C1.401 (3)
C19A—H19A0.9500Cl1C—O3C1.422 (3)
C20A—C21A1.378 (5)Cl1C—O4C1.432 (3)
C20A—H20A0.9500Cl1C—O2C1.441 (3)
C21A—C22A1.379 (5)Cl1D—O2D1.426 (2)
C21A—H21A0.9500Cl1D—O4D1.431 (2)
C22A—H22A0.9500Cl1D—O3D1.443 (2)
C23A—C24A1.462 (4)Cl1D—O1D1.456 (2)
C24A—H24A0.9800Cl1E—O1E1.418 (3)
C24A—H25A0.9800Cl1E—O3E1.424 (3)
C24A—H26A0.9800Cl1E—O4E1.439 (2)
Zn1B—N3B2.020 (3)Cl1E—O2E1.444 (3)
Zn1B—O1B2.025 (2)Cl1F—O4F1.406 (4)
Zn1B—N4B2.040 (3)Cl1F—O2F1.411 (5)
Zn1B—N5B2.043 (3)Cl1F—O1F1.420 (4)
Zn1B—N2B2.240 (2)Cl1F—O3F1.443 (5)
O1B—C9B1.254 (3)Cl1G—O3G1.410 (5)
N1B—C9B1.324 (4)Cl1G—O4G1.412 (5)
N1B—C1B1.437 (4)Cl1G—O1G1.436 (5)
N1B—H1B0.8800Cl1G—O2G1.456 (4)
N2B—C11B1.466 (4)
N4A—Zn1A—N3A157.06 (10)C1B—N1B—H1B118.6
N4A—Zn1A—N5A99.87 (10)C11B—N2B—C10B114.4 (3)
N3A—Zn1A—N5A102.02 (10)C11B—N2B—C17B112.9 (3)
N4A—Zn1A—O1A89.86 (9)C10B—N2B—C17B112.5 (2)
N3A—Zn1A—O1A94.60 (10)C11B—N2B—Zn1B106.84 (18)
N5A—Zn1A—O1A95.95 (9)C10B—N2B—Zn1B107.45 (18)
N4A—Zn1A—N2A79.92 (10)C17B—N2B—Zn1B101.59 (18)
N3A—Zn1A—N2A78.72 (10)C12B—N3B—C13B119.3 (3)
N5A—Zn1A—N2A176.00 (9)C12B—N3B—Zn1B117.1 (2)
O1A—Zn1A—N2A80.06 (9)C13B—N3B—Zn1B123.0 (2)
N4A—Zn1A—O1D90.82 (9)C19B—N4B—C18B119.9 (3)
N3A—Zn1A—O1D81.08 (9)C19B—N4B—Zn1B125.2 (2)
N5A—Zn1A—O1D93.57 (9)C18B—N4B—Zn1B114.8 (2)
O1A—Zn1A—O1D170.19 (8)C23B—N5B—Zn1B175.6 (3)
N2A—Zn1A—O1D90.42 (9)C6B—C1B—C2B122.3 (3)
C9A—O1A—Zn1A116.2 (2)C6B—C1B—N1B119.0 (3)
C9A—N1A—C1A123.5 (3)C2B—C1B—N1B118.7 (3)
C9A—N1A—H1A118.2C3B—C2B—C1B117.7 (3)
C1A—N1A—H1A118.2C3B—C2B—C7B120.8 (3)
C17A—N2A—C11A114.3 (3)C1B—C2B—C7B121.5 (3)
C17A—N2A—C10A112.7 (3)C4B—C3B—C2B120.8 (4)
C11A—N2A—C10A112.0 (3)C4B—C3B—H3B119.6
C17A—N2A—Zn1A105.74 (18)C2B—C3B—H3B119.6
C11A—N2A—Zn1A104.13 (19)C5B—C4B—C3B120.5 (4)
C10A—N2A—Zn1A107.15 (18)C5B—C4B—H4B119.8
C13A—N3A—C12A120.1 (3)C3B—C4B—H4B119.8
C13A—N3A—Zn1A125.0 (2)C4B—C5B—C6B121.1 (4)
C12A—N3A—Zn1A114.9 (2)C4B—C5B—H5B119.4
C19A—N4A—C18A118.7 (3)C6B—C5B—H5B119.4
C19A—N4A—Zn1A124.3 (2)C5B—C6B—C1B117.6 (3)
C18A—N4A—Zn1A116.3 (2)C5B—C6B—C8B120.4 (3)
C23A—N5A—Zn1A173.9 (3)C1B—C6B—C8B122.0 (3)
C6A—C1A—C2A122.6 (3)C2B—C7B—H71B109.5
C6A—C1A—N1A120.1 (3)C2B—C7B—H72B109.5
C2A—C1A—N1A117.3 (3)H71B—C7B—H72B109.5
C3A—C2A—C1A117.4 (4)C2B—C7B—H73B109.5
C3A—C2A—C7A121.4 (3)H71B—C7B—H73B109.5
C1A—C2A—C7A121.2 (3)H72B—C7B—H73B109.5
C4A—C3A—C2A120.7 (4)C6B—C8B—H81B109.5
C4A—C3A—H3A119.6C6B—C8B—H82B109.5
C2A—C3A—H3A119.6H81B—C8B—H82B109.5
C3A—C4A—C5A120.9 (4)C6B—C8B—H83B109.5
C3A—C4A—H4A119.5H81B—C8B—H83B109.5
C5A—C4A—H4A119.5H82B—C8B—H83B109.5
C4A—C5A—C6A120.7 (4)O1B—C9B—N1B121.8 (3)
C4A—C5A—H5A119.6O1B—C9B—C10B121.6 (3)
C6A—C5A—H5A119.6N1B—C9B—C10B116.4 (2)
C1A—C6A—C5A117.6 (4)N2B—C10B—C9B111.4 (2)
C1A—C6A—C8A122.4 (3)N2B—C10B—H10B109.3
C5A—C6A—C8A119.9 (4)C9B—C10B—H10B109.3
C2A—C7A—H71A109.5N2B—C10B—H9B109.3
C2A—C7A—H72A109.5C9B—C10B—H9B109.3
H71A—C7A—H72A109.5H10B—C10B—H9B108.0
C2A—C7A—H73A109.5N2B—C11B—C12B112.2 (2)
H71A—C7A—H73A109.5N2B—C11B—H11B109.2
H72A—C7A—H73A109.5C12B—C11B—H11B109.2
C6A—C8A—H81A109.5N2B—C11B—H12B109.2
C6A—C8A—H82A109.5C12B—C11B—H12B109.2
H81A—C8A—H82A109.5H11B—C11B—H12B107.9
C6A—C8A—H83A109.5N3B—C12B—C16B121.2 (3)
H81A—C8A—H83A109.5N3B—C12B—C11B117.3 (3)
H82A—C8A—H83A109.5C16B—C12B—C11B121.4 (3)
O1A—C9A—N1A122.1 (3)N3B—C13B—C14B122.1 (3)
O1A—C9A—C10A120.6 (3)N3B—C13B—H13B118.9
N1A—C9A—C10A117.2 (3)C14B—C13B—H13B118.9
N2A—C10A—C9A112.8 (2)C13B—C14B—C15B118.3 (3)
N2A—C10A—H10A109.0C13B—C14B—H14B120.9
C9A—C10A—H10A109.0C15B—C14B—H14B120.9
N2A—C10A—H9A109.0C16B—C15B—C14B119.4 (3)
C9A—C10A—H9A109.0C16B—C15B—H15B120.3
H10A—C10A—H9A107.8C14B—C15B—H15B120.3
N2A—C11A—C12A110.5 (3)C12B—C16B—C15B119.7 (3)
N2A—C11A—H11A109.6C12B—C16B—H16B120.1
C12A—C11A—H11A109.6C15B—C16B—H16B120.1
N2A—C11A—H12A109.6N2B—C17B—C18B110.5 (3)
C12A—C11A—H12A109.6N2B—C17B—H17B109.5
H11A—C11A—H12A108.1C18B—C17B—H17B109.5
N3A—C12A—C16A120.1 (4)N2B—C17B—H18B109.5
N3A—C12A—C11A117.8 (3)C18B—C17B—H18B109.5
C16A—C12A—C11A122.0 (3)H17B—C17B—H18B108.1
N3A—C13A—C14A121.8 (4)N4B—C18B—C22B120.0 (4)
N3A—C13A—H13A119.1N4B—C18B—C17B116.7 (3)
C14A—C13A—H13A119.1C22B—C18B—C17B123.3 (3)
C13A—C14A—C15A118.4 (4)N4B—C19B—C20B122.1 (4)
C13A—C14A—H14A120.8N4B—C19B—H19B118.9
C15A—C14A—H14A120.8C20B—C19B—H19B118.9
C16A—C15A—C14A119.5 (4)C21B—C20B—C19B119.1 (4)
C16A—C15A—H15A120.2C21B—C20B—H20B120.4
C14A—C15A—H15A120.2C19B—C20B—H20B120.4
C15A—C16A—C12A120.0 (4)C20B—C21B—C22B119.4 (4)
C15A—C16A—H16A120.0C20B—C21B—H21B120.3
C12A—C16A—H16A120.0C22B—C21B—H21B120.3
N2A—C17A—C18A112.6 (3)C21B—C22B—C18B119.4 (4)
N2A—C17A—H17A109.1C21B—C22B—H22B120.3
C18A—C17A—H17A109.1C18B—C22B—H22B120.3
N2A—C17A—H18A109.1N5B—C23B—C24B179.5 (4)
C18A—C17A—H18A109.1C23B—C24B—H24B109.5
H17A—C17A—H18A107.8C23B—C24B—H25B109.5
N4A—C18A—C22A121.0 (3)H24B—C24B—H25B109.5
N4A—C18A—C17A116.1 (3)C23B—C24B—H26B109.5
C22A—C18A—C17A122.8 (3)H24B—C24B—H26B109.5
N4A—C19A—C20A122.3 (3)H25B—C24B—H26B109.5
N4A—C19A—H19A118.8O1C—Cl1C—O3C109.8 (2)
C20A—C19A—H19A118.8O1C—Cl1C—O4C110.52 (18)
C19A—C20A—C21A119.3 (4)O3C—Cl1C—O4C110.57 (19)
C19A—C20A—H20A120.4O1C—Cl1C—O2C109.3 (2)
C21A—C20A—H20A120.4O3C—Cl1C—O2C108.43 (18)
C20A—C21A—C22A118.7 (3)O4C—Cl1C—O2C108.26 (17)
C20A—C21A—H21A120.7O2D—Cl1D—O4D110.39 (15)
C22A—C21A—H21A120.7O2D—Cl1D—O3D110.17 (13)
C21A—C22A—C18A120.0 (3)O4D—Cl1D—O3D110.13 (14)
C21A—C22A—H22A120.0O2D—Cl1D—O1D109.92 (14)
C18A—C22A—H22A120.0O4D—Cl1D—O1D108.68 (14)
N5A—C23A—C24A179.4 (4)O3D—Cl1D—O1D107.48 (13)
C23A—C24A—H24A109.5Cl1D—O1D—Zn1A131.72 (14)
C23A—C24A—H25A109.5O1E—Cl1E—O3E111.6 (2)
H24A—C24A—H25A109.5O1E—Cl1E—O4E108.61 (16)
C23A—C24A—H26A109.5O3E—Cl1E—O4E107.69 (16)
H24A—C24A—H26A109.5O1E—Cl1E—O2E109.80 (17)
H25A—C24A—H26A109.5O3E—Cl1E—O2E109.52 (18)
N3B—Zn1B—O1B121.54 (9)O4E—Cl1E—O2E109.54 (16)
N3B—Zn1B—N4B129.65 (10)O4F—Cl1F—O2F108.0 (7)
O1B—Zn1B—N4B99.28 (9)O4F—Cl1F—O1F110.9 (4)
N3B—Zn1B—N5B102.79 (10)O2F—Cl1F—O1F107.3 (7)
O1B—Zn1B—N5B96.10 (9)O4F—Cl1F—O3F105.8 (6)
N4B—Zn1B—N5B100.51 (11)O2F—Cl1F—O3F112.3 (9)
N3B—Zn1B—N2B80.29 (10)O1F—Cl1F—O3F112.4 (8)
O1B—Zn1B—N2B79.43 (8)O3G—Cl1G—O4G113.2 (8)
N4B—Zn1B—N2B79.72 (10)O3G—Cl1G—O1G106.8 (6)
N5B—Zn1B—N2B175.48 (9)O4G—Cl1G—O1G114.6 (9)
C9B—O1B—Zn1B117.38 (19)O3G—Cl1G—O2G102.2 (7)
C9B—N1B—C1B122.8 (2)O4G—Cl1G—O2G109.1 (10)
C9B—N1B—H1B118.6O1G—Cl1G—O2G110.2 (7)
N4A—Zn1A—O1A—C9A−76.9 (3)N3B—Zn1B—O1B—C9B84.3 (2)
N3A—Zn1A—O1A—C9A80.6 (3)N4B—Zn1B—O1B—C9B−64.9 (2)
N5A—Zn1A—O1A—C9A−176.8 (3)N5B—Zn1B—O1B—C9B−166.7 (2)
N2A—Zn1A—O1A—C9A2.9 (2)N2B—Zn1B—O1B—C9B12.7 (2)
O1D—Zn1A—O1A—C9A17.1 (7)N3B—Zn1B—N2B—C11B−15.95 (19)
N4A—Zn1A—N2A—C17A−20.83 (19)O1B—Zn1B—N2B—C11B108.93 (19)
N3A—Zn1A—N2A—C17A150.8 (2)N4B—Zn1B—N2B—C11B−149.5 (2)
N5A—Zn1A—N2A—C17A−108.1 (15)N5B—Zn1B—N2B—C11B117.2 (13)
O1A—Zn1A—N2A—C17A−112.5 (2)N3B—Zn1B—N2B—C10B−139.1 (2)
O1D—Zn1A—N2A—C17A69.94 (19)O1B—Zn1B—N2B—C10B−14.2 (2)
N4A—Zn1A—N2A—C11A−141.6 (2)N4B—Zn1B—N2B—C10B87.4 (2)
N3A—Zn1A—N2A—C11A30.02 (19)N5B—Zn1B—N2B—C10B−5.9 (14)
N5A—Zn1A—N2A—C11A131.2 (15)N3B—Zn1B—N2B—C17B102.59 (19)
O1A—Zn1A—N2A—C11A126.8 (2)O1B—Zn1B—N2B—C17B−132.5 (2)
O1D—Zn1A—N2A—C11A−50.80 (19)N4B—Zn1B—N2B—C17B−30.95 (19)
N4A—Zn1A—N2A—C10A99.6 (2)N5B—Zn1B—N2B—C17B−124.2 (13)
N3A—Zn1A—N2A—C10A−88.8 (2)O1B—Zn1B—N3B—C12B−68.6 (2)
N5A—Zn1A—N2A—C10A12.3 (16)N4B—Zn1B—N3B—C12B70.3 (2)
O1A—Zn1A—N2A—C10A7.9 (2)N5B—Zn1B—N3B—C12B−174.1 (2)
O1D—Zn1A—N2A—C10A−169.7 (2)N2B—Zn1B—N3B—C12B2.5 (2)
N4A—Zn1A—N3A—C13A−176.7 (2)O1B—Zn1B—N3B—C13B120.1 (2)
N5A—Zn1A—N3A—C13A−14.4 (3)N4B—Zn1B—N3B—C13B−101.0 (2)
O1A—Zn1A—N3A—C13A82.7 (2)N5B—Zn1B—N3B—C13B14.6 (3)
N2A—Zn1A—N3A—C13A161.6 (2)N2B—Zn1B—N3B—C13B−168.8 (2)
O1D—Zn1A—N3A—C13A−106.1 (2)N3B—Zn1B—N4B—C19B131.4 (2)
N4A—Zn1A—N3A—C12A5.3 (4)O1B—Zn1B—N4B—C19B−83.1 (2)
N5A—Zn1A—N3A—C12A167.6 (2)N5B—Zn1B—N4B—C19B14.9 (3)
O1A—Zn1A—N3A—C12A−95.3 (2)N2B—Zn1B—N4B—C19B−160.5 (2)
N2A—Zn1A—N3A—C12A−16.4 (2)N3B—Zn1B—N4B—C18B−53.5 (2)
O1D—Zn1A—N3A—C12A75.9 (2)O1B—Zn1B—N4B—C18B92.0 (2)
N3A—Zn1A—N4A—C19A173.0 (2)N5B—Zn1B—N4B—C18B−170.0 (2)
N5A—Zn1A—N4A—C19A10.6 (2)N2B—Zn1B—N4B—C18B14.6 (2)
O1A—Zn1A—N4A—C19A−85.5 (2)N3B—Zn1B—N5B—C23B−119 (3)
N2A—Zn1A—N4A—C19A−165.4 (2)O1B—Zn1B—N5B—C23B116 (3)
O1D—Zn1A—N4A—C19A104.3 (2)N4B—Zn1B—N5B—C23B16 (3)
N3A—Zn1A—N4A—C18A−15.9 (4)N2B—Zn1B—N5B—C23B108 (3)
N5A—Zn1A—N4A—C18A−178.4 (2)C9B—N1B—C1B—C6B−68.9 (4)
O1A—Zn1A—N4A—C18A85.6 (2)C9B—N1B—C1B—C2B111.4 (3)
N2A—Zn1A—N4A—C18A5.7 (2)C6B—C1B—C2B—C3B0.3 (5)
O1D—Zn1A—N4A—C18A−84.6 (2)N1B—C1B—C2B—C3B180.0 (3)
N4A—Zn1A—N5A—C23A−40 (3)C6B—C1B—C2B—C7B−178.7 (3)
N3A—Zn1A—N5A—C23A146 (3)N1B—C1B—C2B—C7B1.0 (4)
O1A—Zn1A—N5A—C23A50 (3)C1B—C2B—C3B—C4B0.2 (5)
N2A—Zn1A—N5A—C23A46 (3)C7B—C2B—C3B—C4B179.2 (4)
O1D—Zn1A—N5A—C23A−132 (3)C2B—C3B—C4B—C5B−0.9 (6)
C9A—N1A—C1A—C6A−68.6 (5)C3B—C4B—C5B—C6B1.1 (6)
C9A—N1A—C1A—C2A111.2 (4)C4B—C5B—C6B—C1B−0.6 (6)
C6A—C1A—C2A—C3A0.4 (5)C4B—C5B—C6B—C8B179.3 (4)
N1A—C1A—C2A—C3A−179.4 (3)C2B—C1B—C6B—C5B−0.1 (5)
C6A—C1A—C2A—C7A179.4 (3)N1B—C1B—C6B—C5B−179.8 (3)
N1A—C1A—C2A—C7A−0.4 (4)C2B—C1B—C6B—C8B180.0 (3)
C1A—C2A—C3A—C4A0.1 (5)N1B—C1B—C6B—C8B0.3 (5)
C7A—C2A—C3A—C4A−178.9 (3)Zn1B—O1B—C9B—N1B168.3 (2)
C2A—C3A—C4A—C5A−0.5 (6)Zn1B—O1B—C9B—C10B−8.3 (4)
C3A—C4A—C5A—C6A0.5 (6)C1B—N1B—C9B—O1B−7.9 (5)
C2A—C1A—C6A—C5A−0.4 (5)C1B—N1B—C9B—C10B168.9 (3)
N1A—C1A—C6A—C5A179.4 (3)C11B—N2B—C10B—C9B−104.3 (3)
C2A—C1A—C6A—C8A179.9 (3)C17B—N2B—C10B—C9B125.1 (3)
N1A—C1A—C6A—C8A−0.4 (5)Zn1B—N2B—C10B—C9B14.1 (3)
C4A—C5A—C6A—C1A−0.1 (6)O1B—C9B—C10B—N2B−5.3 (5)
C4A—C5A—C6A—C8A179.7 (4)N1B—C9B—C10B—N2B177.9 (3)
Zn1A—O1A—C9A—N1A170.2 (3)C10B—N2B—C11B—C12B144.5 (3)
Zn1A—O1A—C9A—C10A−14.0 (4)C17B—N2B—C11B—C12B−85.1 (3)
C1A—N1A—C9A—O1A3.1 (5)Zn1B—N2B—C11B—C12B25.7 (3)
C1A—N1A—C9A—C10A−172.8 (3)C13B—N3B—C12B—C16B0.3 (5)
C17A—N2A—C10A—C9A99.8 (3)Zn1B—N3B—C12B—C16B−171.4 (3)
C11A—N2A—C10A—C9A−129.7 (3)C13B—N3B—C12B—C11B−176.3 (3)
Zn1A—N2A—C10A—C9A−16.1 (3)Zn1B—N3B—C12B—C11B12.1 (4)
O1A—C9A—C10A—N2A21.3 (5)N2B—C11B—C12B—N3B−26.7 (4)
N1A—C9A—C10A—N2A−162.7 (3)N2B—C11B—C12B—C16B156.8 (3)
C17A—N2A—C11A—C12A−153.6 (3)C12B—N3B—C13B—C14B0.2 (5)
C10A—N2A—C11A—C12A76.8 (3)Zn1B—N3B—C13B—C14B171.3 (2)
Zn1A—N2A—C11A—C12A−38.7 (3)N3B—C13B—C14B—C15B−0.4 (5)
C13A—N3A—C12A—C16A1.8 (4)C13B—C14B—C15B—C16B0.1 (5)
Zn1A—N3A—C12A—C16A179.9 (2)N3B—C12B—C16B—C15B−0.5 (5)
C13A—N3A—C12A—C11A−179.7 (3)C11B—C12B—C16B—C15B175.9 (3)
Zn1A—N3A—C12A—C11A−1.6 (3)C14B—C15B—C16B—C12B0.3 (5)
N2A—C11A—C12A—N3A29.7 (4)C11B—N2B—C17B—C18B156.5 (2)
N2A—C11A—C12A—C16A−151.8 (3)C10B—N2B—C17B—C18B−72.2 (3)
C12A—N3A—C13A—C14A−0.1 (4)Zn1B—N2B—C17B—C18B42.4 (3)
Zn1A—N3A—C13A—C14A−178.0 (2)C19B—N4B—C18B—C22B0.2 (4)
N3A—C13A—C14A—C15A−1.9 (5)Zn1B—N4B—C18B—C22B−175.1 (2)
C13A—C14A—C15A—C16A2.1 (5)C19B—N4B—C18B—C17B−178.2 (3)
C14A—C15A—C16A—C12A−0.5 (6)Zn1B—N4B—C18B—C17B6.5 (3)
N3A—C12A—C16A—C15A−1.5 (5)N2B—C17B—C18B—N4B−36.1 (3)
C11A—C12A—C16A—C15A−179.9 (3)N2B—C17B—C18B—C22B145.5 (3)
C11A—N2A—C17A—C18A146.0 (3)C18B—N4B—C19B—C20B−0.8 (5)
C10A—N2A—C17A—C18A−84.6 (3)Zn1B—N4B—C19B—C20B174.1 (3)
Zn1A—N2A—C17A—C18A32.1 (3)N4B—C19B—C20B—C21B1.2 (5)
C19A—N4A—C18A—C22A0.4 (4)C19B—C20B—C21B—C22B−1.0 (6)
Zn1A—N4A—C18A—C22A−171.2 (2)C20B—C21B—C22B—C18B0.4 (5)
C19A—N4A—C18A—C17A−177.1 (3)N4B—C18B—C22B—C21B0.0 (5)
Zn1A—N4A—C18A—C17A11.3 (3)C17B—C18B—C22B—C21B178.2 (3)
N2A—C17A—C18A—N4A−30.9 (4)Zn1B—N5B—C23B—C24B−129 (51)
N2A—C17A—C18A—C22A151.6 (3)O2D—Cl1D—O1D—Zn1A−38.5 (2)
C18A—N4A—C19A—C20A0.4 (4)O4D—Cl1D—O1D—Zn1A82.4 (2)
Zn1A—N4A—C19A—C20A171.2 (2)O3D—Cl1D—O1D—Zn1A−158.46 (16)
N4A—C19A—C20A—C21A−0.3 (5)N4A—Zn1A—O1D—Cl1D−22.45 (19)
C19A—C20A—C21A—C22A−0.4 (5)N3A—Zn1A—O1D—Cl1D179.11 (19)
C20A—C21A—C22A—C18A1.2 (5)N5A—Zn1A—O1D—Cl1D77.49 (19)
N4A—C18A—C22A—C21A−1.2 (5)O1A—Zn1A—O1D—Cl1D−116.4 (5)
C17A—C18A—C22A—C21A176.2 (3)N2A—Zn1A—O1D—Cl1D−102.37 (19)
Zn1A—N5A—C23A—C24A−46 (40)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1A—H1A···O3Di0.882.002.868 (3)171
N1B—H1B···O4Eii0.882.152.979 (3)157
N1B—H1B···O3Eii0.882.413.138 (4)141
Symmetry codes: (i) x, −y+1, z+1/2; (ii) x, −y, z+1/2.

Experimental details

Crystal data
Chemical formula[Zn(C22H24N4O)(C2H3N)][Zn(ClO4)(C22H24N4O)(C2H3N)](ClO4)3
Mr1331.59
Crystal system, space groupMonoclinic, C2/c
Temperature (K)105
a, b, c (Å)41.253 (8), 15.057 (3), 20.809 (4)
β (°) 106.106 (2)
V (Å3)12418 (4)
Z8
Radiation typeMo Kα
µ (mm−1)1.03
Crystal size (mm)0.91 × 0.29 × 0.22
Data collection
DiffractometerBruker APEXII CCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2007)
Tmin, Tmax0.531, 0.798
No. of measured, independent and
observed [I > 2σ(I)] reflections		43906, 10987, 8503
Rint0.051
(sin θ/λ)max (Å−1)0.597
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.045, 0.124, 1.07
No. of reflections10987
No. of parameters782
No. of restraints8
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å−3)0.89, −0.66

Computer programs: APEX2 (Bruker, 2007), SAINT-Plus (Bruker, 2007), SHELXTL (Sheldrick, 2008) and Mercury (Macrae et al., 2008).

Selected bond lengths (Å) top
Zn1A—N4A2.058 (3)Zn1B—N3B2.020 (3)
Zn1A—N3A2.059 (3)Zn1B—O1B2.025 (2)
Zn1A—N5A2.060 (3)Zn1B—N4B2.040 (3)
Zn1A—O1A2.087 (2)Zn1B—N5B2.043 (3)
Zn1A—N2A2.236 (2)Zn1B—N2B2.240 (2)
Zn1A—O1D2.310 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1A—H1A···O3Di0.882.002.868 (3)171
N1B—H1B···O4Eii0.882.152.979 (3)157
N1B—H1B···O3Eii0.882.413.138 (4)141
Symmetry codes: (i) x, −y+1, z+1/2; (ii) x, −y, z+1/2.
 

Acknowledgements

The work has been partly supported by Statoil Norge AS.

References

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ISSN: 2056-9890
Volume 69| Part 2| February 2013| Pages m112-m113
doi:10.1107/S1600536813001396
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