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Acta Cryst. (2009). E65, m655    [ doi:10.1107/S1600536809017693 ]

2,2'-(Hexane-1,6-diyl)diisoquinolinium tetrachloridozincate(II)

P.-H. Ma, Z.-F. Fan, Y.-Q. Zhang, X. Xiao and S.-F. Xue

Abstract top

The asymmetric unit of the title compound, (C24H26N2)[ZnCl4], consists of two 2,2'-(hexane-1,6-diyl)diisoquinolinium cations and two [ZnCl4]2- complex anions. The [ZnCl4]2- anions have a distorted tetrahedral geometry. The dihedral angles between the isoquinoline rings of the two cations are nearly equal [16.1 (2) and 16.3 (2)°]. In the crystal structure, the ordered linear formation is aggregated by weak intermolecular [pi]-[pi] stacking interactions between neighboring isoquinoline pyridine rings with a centroid-centroid distance of 3.779 (4) Å.

Comment top

As part of our ongoing investigation on quinoline compounds, we present here the crystal structure of the compound with multiple functional groups, which can develop strong intermolecular interactions with cucurbit[n]urils (CB[n]) (Freeman et al., 1981; Day & Arnold, 2000; Day et al., 2002; Kim et al., 2000; Wu et al., 2008).

The crystal structure of the title compound (Fig. 1) consists of organic cations and anionic complex [ZnCl4]2-. The [ZnCl4]2- anion is a distorted tetrahedron with Zn–Cl bonds distances ranging from 2.2674 (16)Å to 2.3023 (14)Å (table 1). There are dihedral angles of 16.1 (2)Å between the N1 isoquinolyl ring (N1/C1-C9) and N2 isoquinolyl ring (N2/C16-C24), 16.3 (2)Å between the N3 isoquinolyl ring (N3/C25-C33) and N4 isoquinolyl ring (N4/C40-C48) of organic cations, respectively. The ordered linear formation was aggregated by intermolecular weak π-π stacking interactions between neighboring pyridine rings of isoquinolyl in the crystal structure. (Pan & Xu, 2004).

Related literature top

For general background to quinoline compounds, see: Day & Arnold (2000); Day et al. (2002); Freeman et al. (1981); Kim et al. (2000); Wu et al. (2008). For a related structure, see: Pan & Xu (2004).

Experimental top

A solution of 1,6-dibromine-hexane (2.44 g, 0.01 mol) was added to a stirred solution of isoquinoline (2.58 g, 0.02 mol) in 1,4-dioxane (50 ml) at 373 K in a period of 5 h. After cooling to room temperature, the mixture was filtered. The residue was added to an aqueous solution (50 ml) of ZnCl2 (0.01 mol, 1.37 g). After stirring for 2 h, the solution was filtered. Colorless single crystals of the title compound were obtained from the filtrate after 3 weeks.

Refinement top

H atoms were placed in calculated positions with C—H = 0.93Å (aromatic) or 0.97Å (methylene), and refined in riding mode with Uiso(H) = 1.2Ueq(C).

Computing details top

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT (Bruker, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top
[Figure 1] Fig. 1. The molecular structure of (I) showing the atom-labeling scheme. Displacement ellipsoids are drawn at the 50% probability level
2,2'-(Hexane-1,6-diyl)diisoquinolinium tetrachloridozincate(II) top
Crystal data top
(C24H26N2)[ZnCl4]F000 = 1128
Mr = 549.66Dx = 1.495 Mg m−3
Monoclinic, P21Mo Kα radiation
λ = 0.71073 Å
Hall symbol: p 2ybCell parameters from 8189 reflections
a = 10.066 (2) Åθ = 1.7–25.0º
b = 24.666 (5) ŵ = 1.46 mm−1
c = 10.392 (2) ÅT = 293 K
β = 108.826 (2)ºPrism, colorless
V = 2442.2 (8) Å30.24 × 0.22 × 0.19 mm
Z = 4
Data collection top
Bruker SMART CCD area-detector
diffractometer		8189 independent reflections
Radiation source: fine-focus sealed tube6898 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.027
T = 293 Kθmax = 25.0º
φ and ω scansθmin = 1.7º
Absorption correction: multi-scan
(SADABS; Bruker, 2005)		h = −11→11
Tmin = 0.708, Tmax = 0.755k = −29→29
11146 measured reflectionsl = −12→12
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.041  w = 1/[σ2(Fo2) + (0.0514P)2 + ]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.101(Δ/σ)max < 0.001
S = 1.05Δρmax = 0.53 e Å−3
8189 reflectionsΔρmin = −0.27 e Å−3
559 parametersExtinction correction: none
1 restraintAbsolute structure: Flack (1983)
Primary atom site location: structure-invariant direct methodsFlack parameter: 0.263 (12)
Secondary atom site location: difference Fourier map
Crystal data top
(C24H26N2)[ZnCl4]V = 2442.2 (8) Å3
Mr = 549.66Z = 4
Monoclinic, P21Mo Kα
a = 10.066 (2) ŵ = 1.46 mm−1
b = 24.666 (5) ÅT = 293 K
c = 10.392 (2) Å0.24 × 0.22 × 0.19 mm
β = 108.826 (2)º
Data collection top
Bruker SMART CCD area-detector
diffractometer		8189 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2005)		6898 reflections with I > 2σ(I)
Tmin = 0.708, Tmax = 0.755Rint = 0.027
11146 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.041H-atom parameters constrained
wR(F2) = 0.101Δρmax = 0.53 e Å−3
S = 1.05Δρmin = −0.27 e Å−3
8189 reflectionsAbsolute structure: Flack (1983)
559 parametersFlack parameter: 0.263 (12)
1 restraint
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. 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 (Å2) top
xyzUiso*/Ueq
C10.6424 (7)0.8906 (2)0.5696 (6)0.0438 (16)
H10.70120.89390.65900.053*
C20.5037 (7)0.8871 (2)0.5450 (6)0.0402 (14)
H20.46740.88850.61670.048*
C30.4126 (6)0.8813 (2)0.4109 (6)0.0327 (14)
C40.4749 (6)0.8794 (2)0.3035 (6)0.0331 (13)
C50.6204 (6)0.8838 (2)0.3404 (6)0.0340 (14)
H50.66220.88270.27260.041*
C60.2646 (7)0.8791 (2)0.3751 (7)0.0445 (15)
H60.22280.87930.44280.053*
C70.1821 (6)0.8766 (2)0.2405 (6)0.0449 (15)
H70.08490.87660.21780.054*
C80.2448 (6)0.8740 (2)0.1369 (6)0.0381 (14)
H80.18810.87130.04660.046*
C90.3871 (6)0.8754 (2)0.1673 (6)0.0363 (14)
H90.42650.87370.09780.044*
C100.8554 (6)0.8982 (3)0.5011 (7)0.0489 (18)
H10A0.88350.88900.42290.059*
H10B0.90520.87440.57530.059*
C110.8960 (6)0.9567 (2)0.5418 (6)0.0413 (14)
H11A0.88360.96370.62900.050*
H11B0.83330.98060.47540.050*
C121.0468 (6)0.9698 (3)0.5517 (6)0.0444 (16)
H12A1.05690.96430.46280.053*
H12B1.06371.00790.57410.053*
C131.1580 (6)0.9373 (3)0.6536 (5)0.0459 (16)
H13A1.24760.94490.64130.055*
H13B1.13810.89910.63470.055*
C141.1717 (5)0.9480 (3)0.8037 (5)0.0375 (13)
H14A1.07990.94500.81470.045*
H14B1.23180.92050.86030.045*
C151.2317 (7)1.0033 (2)0.8507 (6)0.0423 (15)
H15A1.32261.00680.83790.051*
H15B1.17021.03090.79630.051*
C161.3714 (6)1.0060 (2)1.0920 (6)0.0343 (14)
H161.44840.99601.06650.041*
C171.3897 (6)1.0148 (2)1.2312 (6)0.0313 (13)
C181.2714 (6)1.0299 (2)1.2658 (6)0.0399 (15)
C191.1421 (6)1.0346 (2)1.1615 (7)0.0464 (16)
H191.06231.04431.18270.056*
C201.1325 (6)1.0252 (2)1.0313 (6)0.0444 (15)
H201.04571.02790.96380.053*
C211.5238 (6)1.0102 (2)1.3312 (6)0.0321 (14)
H211.60161.00091.30630.039*
C221.5376 (7)1.0196 (2)1.4624 (6)0.0445 (15)
H221.62521.01561.52810.053*
C231.4217 (8)1.0354 (2)1.5025 (7)0.0524 (19)
H231.43391.04221.59360.063*
C241.2900 (7)1.0407 (2)1.4061 (7)0.0473 (16)
H241.21391.05131.43230.057*
C250.7866 (6)0.1287 (3)0.4333 (6)0.0461 (15)
H250.87250.12600.50220.055*
C260.7785 (7)0.1196 (3)0.3046 (7)0.0488 (17)
H260.85960.11090.28450.059*
C270.6484 (6)0.1228 (2)0.1972 (6)0.0355 (13)
C280.5293 (6)0.1381 (2)0.2328 (6)0.0297 (13)
C290.5447 (6)0.1472 (2)0.3690 (5)0.0289 (12)
H290.46680.15710.39320.035*
C300.6318 (7)0.1124 (3)0.0592 (6)0.0437 (16)
H300.70860.10190.03390.052*
C310.5034 (7)0.1177 (2)−0.0365 (6)0.0439 (15)
H310.49430.1110−0.12700.053*
C320.3841 (6)0.1330 (2)−0.0034 (5)0.0382 (14)
H320.29750.1366−0.07080.046*
C330.3975 (6)0.1422 (2)0.1286 (6)0.0346 (13)
H330.31850.15160.15150.041*
C340.6825 (6)0.1510 (2)0.6086 (6)0.0400 (14)
H34A0.74110.12260.66280.048*
H34B0.59090.14850.62030.048*
C350.7466 (5)0.2055 (2)0.6595 (5)0.0310 (11)
H35A0.68950.23380.60340.037*
H35B0.83930.20750.65030.037*
C360.7584 (5)0.2156 (2)0.8064 (5)0.0322 (13)
H36A0.66880.20720.81810.039*
H36B0.77630.25390.82570.039*
C370.8733 (5)0.1829 (2)0.9109 (5)0.0372 (14)
H37A0.85630.14470.89030.045*
H37B0.86490.18911.00020.045*
C381.0249 (5)0.1961 (2)0.9173 (5)0.0355 (13)
H38A1.08900.17250.98360.043*
H38B1.03540.18870.82940.043*
C391.0640 (6)0.2547 (2)0.9556 (6)0.0406 (15)
H39A1.01550.27810.87980.049*
H39B1.03420.26461.03240.049*
C401.2976 (6)0.2689 (2)1.1181 (6)0.0328 (13)
H401.25610.27021.18610.039*
C411.4448 (6)0.2733 (2)1.1543 (6)0.0280 (13)
C421.5065 (6)0.2720 (2)1.0519 (6)0.0313 (12)
C431.4151 (6)0.2673 (2)0.9159 (6)0.0360 (14)
H431.45280.26700.84510.043*
C441.2763 (6)0.2631 (2)0.8872 (6)0.0376 (14)
H441.21870.26030.79730.045*
C451.5328 (6)0.2760 (2)1.2922 (6)0.0327 (13)
H451.49310.27631.36160.039*
C461.6741 (6)0.2781 (2)1.3229 (6)0.0358 (14)
H461.73130.28051.41310.043*
C471.7329 (6)0.2767 (2)1.2202 (6)0.0422 (14)
H471.83010.27781.24270.051*
C481.6543 (6)0.2737 (2)1.0885 (6)0.0379 (15)
H481.69720.27281.02160.045*
Cl10.88950 (14)0.88576 (5)0.91266 (15)0.0409 (3)
Cl20.81540 (16)0.97308 (6)1.18102 (13)0.0441 (4)
Cl30.52795 (15)0.91812 (7)0.89273 (15)0.0475 (4)
Cl40.76150 (15)1.02597 (5)0.82706 (13)0.0355 (3)
Cl50.16104 (15)0.12917 (5)0.63448 (13)0.0358 (3)
Cl60.38644 (15)0.24126 (7)0.56637 (15)0.0461 (4)
Cl70.10464 (16)0.18099 (6)0.28203 (13)0.0444 (4)
Cl80.02407 (14)0.26899 (6)0.54912 (14)0.0413 (3)
N10.7007 (5)0.88939 (18)0.4672 (5)0.0365 (11)
N21.2473 (5)1.01179 (18)0.9969 (5)0.0343 (11)
N30.6674 (5)0.14215 (18)0.4643 (5)0.0339 (11)
N41.2176 (5)0.26308 (18)0.9914 (5)0.0363 (12)
Zn10.74988 (6)0.95121 (2)0.95564 (6)0.03348 (16)
Zn20.16703 (6)0.20425 (2)0.50571 (6)0.03468 (16)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.058 (4)0.040 (3)0.031 (4)−0.001 (3)0.011 (3)0.001 (3)
C20.049 (4)0.038 (3)0.037 (4)0.001 (3)0.018 (3)0.003 (3)
C30.042 (4)0.022 (3)0.033 (4)−0.002 (3)0.010 (3)0.004 (2)
C40.040 (3)0.030 (3)0.030 (3)−0.002 (2)0.012 (3)−0.001 (2)
C50.041 (4)0.039 (3)0.026 (4)0.002 (3)0.016 (3)0.001 (3)
C60.055 (4)0.041 (3)0.046 (4)−0.006 (3)0.028 (3)−0.004 (3)
C70.040 (4)0.044 (4)0.049 (4)−0.007 (3)0.012 (3)−0.006 (3)
C80.050 (4)0.036 (3)0.025 (3)−0.003 (3)0.008 (3)0.001 (3)
C90.052 (4)0.035 (3)0.025 (3)0.001 (3)0.016 (3)−0.001 (3)
C100.034 (4)0.053 (4)0.057 (5)0.010 (3)0.011 (3)0.002 (3)
C110.044 (4)0.046 (4)0.032 (3)0.005 (3)0.010 (3)−0.004 (3)
C120.054 (4)0.050 (4)0.031 (4)0.001 (3)0.016 (3)−0.004 (3)
C130.033 (3)0.072 (5)0.034 (4)−0.003 (3)0.013 (3)−0.004 (3)
C140.024 (3)0.054 (3)0.031 (3)−0.004 (3)0.004 (2)−0.003 (3)
C150.052 (4)0.044 (4)0.026 (3)−0.001 (3)0.006 (3)0.005 (3)
C160.031 (3)0.030 (3)0.039 (4)−0.002 (2)0.007 (3)−0.007 (3)
C170.037 (3)0.021 (3)0.040 (4)−0.002 (2)0.018 (3)−0.005 (2)
C180.046 (4)0.030 (3)0.045 (4)−0.009 (3)0.016 (3)−0.006 (3)
C190.038 (4)0.049 (4)0.057 (4)0.003 (3)0.023 (3)−0.007 (3)
C200.032 (3)0.053 (4)0.041 (4)−0.003 (3)0.001 (3)−0.007 (3)
C210.043 (4)0.027 (3)0.027 (3)−0.004 (2)0.013 (3)0.004 (2)
C220.048 (4)0.032 (3)0.047 (4)−0.005 (3)0.006 (3)−0.001 (3)
C230.086 (6)0.038 (4)0.037 (4)−0.015 (4)0.026 (4)−0.004 (3)
C240.052 (4)0.050 (4)0.047 (4)−0.010 (3)0.027 (4)−0.009 (3)
C250.036 (4)0.050 (4)0.045 (4)0.001 (3)0.003 (3)−0.003 (3)
C260.032 (4)0.054 (4)0.062 (5)−0.007 (3)0.018 (3)−0.012 (4)
C270.038 (3)0.034 (3)0.036 (3)−0.010 (3)0.014 (3)−0.007 (3)
C280.036 (3)0.022 (3)0.028 (3)−0.003 (2)0.006 (3)0.002 (2)
C290.037 (3)0.026 (3)0.022 (3)−0.002 (2)0.007 (3)0.003 (2)
C300.051 (4)0.047 (4)0.041 (4)−0.006 (3)0.026 (3)−0.011 (3)
C310.066 (5)0.042 (4)0.022 (3)−0.009 (3)0.013 (3)−0.006 (3)
C320.046 (4)0.034 (3)0.023 (3)−0.002 (3)−0.005 (3)0.004 (2)
C330.041 (3)0.022 (3)0.037 (4)0.005 (2)0.006 (3)−0.003 (2)
C340.048 (4)0.041 (3)0.025 (3)−0.006 (3)0.005 (3)0.001 (3)
C350.031 (3)0.036 (3)0.024 (3)0.000 (2)0.006 (2)0.005 (3)
C360.029 (3)0.035 (3)0.031 (3)−0.004 (2)0.008 (2)−0.005 (2)
C370.033 (3)0.048 (3)0.026 (3)−0.010 (3)0.004 (3)−0.003 (3)
C380.030 (3)0.042 (3)0.026 (3)0.000 (3)−0.002 (2)0.000 (3)
C390.023 (3)0.045 (4)0.046 (4)0.001 (2)0.000 (3)0.000 (3)
C400.037 (3)0.025 (3)0.035 (4)−0.001 (2)0.009 (3)−0.004 (3)
C410.033 (3)0.023 (3)0.027 (3)0.001 (2)0.008 (3)0.001 (2)
C420.040 (3)0.028 (3)0.027 (3)−0.002 (2)0.012 (3)−0.002 (2)
C430.045 (4)0.040 (3)0.023 (3)−0.002 (3)0.011 (3)−0.001 (3)
C440.042 (4)0.045 (3)0.017 (3)−0.004 (3)−0.003 (3)0.003 (3)
C450.046 (4)0.025 (3)0.025 (3)−0.001 (2)0.008 (3)0.000 (2)
C460.035 (3)0.039 (3)0.031 (4)−0.001 (3)0.007 (3)−0.003 (3)
C470.034 (3)0.045 (3)0.041 (4)0.005 (3)0.003 (3)0.004 (3)
C480.036 (3)0.048 (4)0.030 (4)0.002 (3)0.012 (3)0.001 (3)
Cl10.0365 (8)0.0378 (8)0.0471 (9)0.0038 (6)0.0118 (7)0.0051 (7)
Cl20.0472 (9)0.0663 (10)0.0171 (7)−0.0117 (7)0.0082 (7)−0.0044 (6)
Cl30.0333 (8)0.0687 (10)0.0425 (9)−0.0064 (7)0.0152 (7)−0.0095 (8)
Cl40.0477 (9)0.0298 (7)0.0268 (7)0.0028 (6)0.0089 (7)0.0055 (6)
Cl50.0482 (9)0.0368 (7)0.0206 (7)0.0020 (6)0.0087 (6)0.0039 (6)
Cl60.0305 (8)0.0726 (10)0.0371 (9)−0.0096 (7)0.0133 (7)−0.0084 (8)
Cl70.0476 (9)0.0655 (10)0.0196 (7)−0.0127 (7)0.0101 (7)−0.0041 (7)
Cl80.0319 (8)0.0489 (8)0.0412 (9)0.0032 (6)0.0092 (7)0.0054 (7)
N10.039 (3)0.038 (3)0.032 (3)0.006 (2)0.010 (2)0.002 (2)
N20.038 (3)0.036 (3)0.024 (3)−0.001 (2)0.003 (2)−0.001 (2)
N30.034 (3)0.032 (3)0.030 (3)−0.002 (2)0.003 (2)−0.002 (2)
N40.026 (3)0.030 (3)0.048 (3)0.003 (2)0.004 (2)−0.002 (2)
Zn10.0339 (4)0.0408 (4)0.0251 (3)−0.0015 (3)0.0086 (3)0.0010 (3)
Zn20.0316 (4)0.0468 (4)0.0246 (4)−0.0016 (3)0.0077 (3)0.0014 (3)
Geometric parameters (Å, °) top
C1—C21.339 (8)C26—H260.9300
C1—N11.371 (7)C27—C301.413 (8)
C1—H10.9300C27—C281.414 (7)
C2—C31.407 (8)C28—C291.392 (7)
C2—H20.9300C28—C331.420 (7)
C3—C61.415 (8)C29—N31.316 (6)
C3—C41.446 (8)C29—H290.9300
C4—C51.393 (7)C30—C311.359 (8)
C4—C91.410 (8)C30—H300.9300
C5—N11.312 (7)C31—C321.403 (8)
C5—H50.9300C31—H310.9300
C6—C71.378 (8)C32—C331.354 (8)
C6—H60.9300C32—H320.9300
C7—C81.415 (8)C33—H330.9300
C7—H70.9300C34—N31.474 (7)
C8—C91.364 (8)C34—C351.510 (7)
C8—H80.9300C34—H34A0.9700
C9—H90.9300C34—H34B0.9700
C10—N11.497 (7)C35—C361.514 (7)
C10—C111.521 (9)C35—H35A0.9700
C10—H10A0.9700C35—H35B0.9700
C10—H10B0.9700C36—C371.535 (7)
C11—C121.522 (7)C36—H36A0.9700
C11—H11A0.9700C36—H36B0.9700
C11—H11B0.9700C37—C381.541 (7)
C12—C131.501 (8)C37—H37A0.9700
C12—H12A0.9700C37—H37B0.9700
C12—H12B0.9700C38—C391.519 (8)
C13—C141.543 (7)C38—H38A0.9700
C13—H13A0.9700C38—H38B0.9700
C13—H13B0.9700C39—N41.483 (7)
C14—C151.508 (8)C39—H39A0.9700
C14—H14A0.9700C39—H39B0.9700
C14—H14B0.9700C40—N41.311 (7)
C15—N21.491 (7)C40—C411.411 (7)
C15—H15A0.9700C40—H400.9300
C15—H15B0.9700C41—C421.395 (7)
C16—N21.327 (7)C41—C451.423 (7)
C16—C171.414 (8)C42—C481.412 (7)
C16—H160.9300C42—C431.421 (7)
C17—C181.401 (8)C43—C441.334 (7)
C17—C211.418 (7)C43—H430.9300
C18—C191.404 (8)C44—N41.391 (7)
C18—C241.434 (8)C44—H440.9300
C19—C201.345 (8)C45—C461.355 (7)
C19—H190.9300C45—H450.9300
C20—N21.356 (7)C46—C471.378 (7)
C20—H200.9300C46—H460.9300
C21—C221.345 (8)C47—C481.344 (8)
C21—H210.9300C47—H470.9300
C22—C231.414 (8)C48—H480.9300
C22—H220.9300Cl1—Zn12.2773 (15)
C23—C241.386 (9)Cl2—Zn12.2836 (15)
C23—H230.9300Cl3—Zn12.2674 (16)
C24—H240.9300Cl4—Zn12.3023 (14)
C25—C261.333 (8)Cl5—Zn22.2969 (14)
C25—N31.379 (7)Cl6—Zn22.2826 (16)
C25—H250.9300Cl7—Zn22.2770 (15)
C26—C271.422 (8)Cl8—Zn22.2898 (15)
C2—C1—N1122.1 (6)N3—C29—C28121.3 (5)
C2—C1—H1118.9N3—C29—H29119.4
N1—C1—H1118.9C28—C29—H29119.4
C1—C2—C3120.1 (6)C31—C30—C27119.9 (6)
C1—C2—H2120.0C31—C30—H30120.0
C3—C2—H2120.0C27—C30—H30120.0
C2—C3—C6123.9 (5)C30—C31—C32122.2 (5)
C2—C3—C4117.5 (6)C30—C31—H31118.9
C6—C3—C4118.5 (5)C32—C31—H31118.9
C5—C4—C9123.0 (5)C33—C32—C31118.7 (5)
C5—C4—C3117.7 (5)C33—C32—H32120.6
C9—C4—C3119.3 (5)C31—C32—H32120.6
N1—C5—C4122.5 (5)C32—C33—C28121.6 (5)
N1—C5—H5118.8C32—C33—H33119.2
C4—C5—H5118.8C28—C33—H33119.2
C7—C6—C3120.5 (5)N3—C34—C35112.4 (4)
C7—C6—H6119.8N3—C34—H34A109.1
C3—C6—H6119.8C35—C34—H34A109.1
C6—C7—C8120.2 (6)N3—C34—H34B109.1
C6—C7—H7119.9C35—C34—H34B109.1
C8—C7—H7119.9H34A—C34—H34B107.9
C9—C8—C7121.0 (5)C34—C35—C36112.7 (4)
C9—C8—H8119.5C34—C35—H35A109.1
C7—C8—H8119.5C36—C35—H35A109.1
C8—C9—C4120.4 (5)C34—C35—H35B109.1
C8—C9—H9119.8C36—C35—H35B109.1
C4—C9—H9119.8H35A—C35—H35B107.8
N1—C10—C11111.7 (5)C35—C36—C37115.0 (4)
N1—C10—H10A109.3C35—C36—H36A108.5
C11—C10—H10A109.3C37—C36—H36A108.5
N1—C10—H10B109.3C35—C36—H36B108.5
C11—C10—H10B109.3C37—C36—H36B108.5
H10A—C10—H10B107.9H36A—C36—H36B107.5
C10—C11—C12113.1 (5)C36—C37—C38115.4 (5)
C10—C11—H11A109.0C36—C37—H37A108.4
C12—C11—H11A109.0C38—C37—H37A108.4
C10—C11—H11B109.0C36—C37—H37B108.4
C12—C11—H11B109.0C38—C37—H37B108.4
H11A—C11—H11B107.8H37A—C37—H37B107.5
C13—C12—C11115.8 (5)C39—C38—C37112.5 (5)
C13—C12—H12A108.3C39—C38—H38A109.1
C11—C12—H12A108.3C37—C38—H38A109.1
C13—C12—H12B108.3C39—C38—H38B109.1
C11—C12—H12B108.3C37—C38—H38B109.1
H12A—C12—H12B107.4H38A—C38—H38B107.8
C12—C13—C14115.2 (5)N4—C39—C38111.1 (4)
C12—C13—H13A108.5N4—C39—H39A109.4
C14—C13—H13A108.5C38—C39—H39A109.4
C12—C13—H13B108.5N4—C39—H39B109.4
C14—C13—H13B108.5C38—C39—H39B109.4
H13A—C13—H13B107.5H39A—C39—H39B108.0
C15—C14—C13112.2 (5)N4—C40—C41121.9 (5)
C15—C14—H14A109.2N4—C40—H40119.1
C13—C14—H14A109.2C41—C40—H40119.1
C15—C14—H14B109.2C42—C41—C40118.9 (5)
C13—C14—H14B109.2C42—C41—C45119.0 (5)
H14A—C14—H14B107.9C40—C41—C45122.1 (5)
N2—C15—C14110.9 (4)C41—C42—C48118.9 (5)
N2—C15—H15A109.5C41—C42—C43117.1 (5)
C14—C15—H15A109.5C48—C42—C43123.9 (5)
N2—C15—H15B109.5C44—C43—C42121.6 (5)
C14—C15—H15B109.5C44—C43—H43119.2
H15A—C15—H15B108.0C42—C43—H43119.2
N2—C16—C17121.7 (5)C43—C44—N4120.2 (5)
N2—C16—H16119.1C43—C44—H44119.9
C17—C16—H16119.1N4—C44—H44119.9
C18—C17—C16117.5 (5)C46—C45—C41120.3 (5)
C18—C17—C21121.3 (5)C46—C45—H45119.9
C16—C17—C21121.1 (5)C41—C45—H45119.9
C17—C18—C19118.5 (6)C45—C46—C47119.8 (6)
C17—C18—C24117.9 (6)C45—C46—H46120.1
C19—C18—C24123.6 (6)C47—C46—H46120.1
C20—C19—C18120.6 (6)C48—C47—C46122.1 (6)
C20—C19—H19119.7C48—C47—H47119.0
C18—C19—H19119.7C46—C47—H47119.0
C19—C20—N2121.1 (6)C47—C48—C42120.0 (6)
C19—C20—H20119.4C47—C48—H48120.0
N2—C20—H20119.4C42—C48—H48120.0
C22—C21—C17119.5 (6)C5—N1—C1120.2 (5)
C22—C21—H21120.3C5—N1—C10120.6 (5)
C17—C21—H21120.3C1—N1—C10119.1 (5)
C21—C22—C23121.4 (6)C16—N2—C20120.5 (5)
C21—C22—H22119.3C16—N2—C15120.6 (5)
C23—C22—H22119.3C20—N2—C15119.0 (5)
C24—C23—C22120.0 (6)C29—N3—C25121.6 (5)
C24—C23—H23120.0C29—N3—C34121.0 (5)
C22—C23—H23120.0C25—N3—C34117.5 (5)
C23—C24—C18119.9 (6)C40—N4—C44120.3 (5)
C23—C24—H24120.0C40—N4—C39121.3 (5)
C18—C24—H24120.0C44—N4—C39118.4 (5)
C26—C25—N3119.9 (6)Cl3—Zn1—Cl1107.53 (6)
C26—C25—H25120.0Cl3—Zn1—Cl2108.20 (5)
N3—C25—H25120.0Cl1—Zn1—Cl2112.11 (6)
C25—C26—C27121.4 (6)Cl3—Zn1—Cl4110.54 (6)
C25—C26—H26119.3Cl1—Zn1—Cl4107.69 (5)
C27—C26—H26119.3Cl2—Zn1—Cl4110.74 (6)
C30—C27—C28118.8 (5)Cl7—Zn2—Cl6107.83 (6)
C30—C27—C26124.3 (6)Cl7—Zn2—Cl8113.14 (6)
C28—C27—C26117.0 (5)Cl6—Zn2—Cl8106.28 (6)
C29—C28—C27118.9 (5)Cl7—Zn2—Cl5109.94 (6)
C29—C28—C33122.3 (5)Cl6—Zn2—Cl5111.50 (6)
C27—C28—C33118.8 (5)Cl8—Zn2—Cl5108.13 (5)
N1—C1—C2—C30.8 (9)C30—C31—C32—C33−0.5 (9)
C1—C2—C3—C6−177.9 (5)C31—C32—C33—C281.4 (8)
C1—C2—C3—C40.0 (8)C29—C28—C33—C32−179.7 (5)
C2—C3—C4—C5−0.5 (8)C27—C28—C33—C32−1.2 (8)
C6—C3—C4—C5177.6 (5)N3—C34—C35—C36178.3 (4)
C2—C3—C4—C9−178.0 (5)C34—C35—C36—C3773.1 (6)
C6—C3—C4—C90.1 (8)C35—C36—C37—C3864.7 (6)
C9—C4—C5—N1177.5 (5)C36—C37—C38—C3960.8 (6)
C3—C4—C5—N10.1 (8)C37—C38—C39—N4167.1 (5)
C2—C3—C6—C7176.2 (6)N4—C40—C41—C420.8 (7)
C4—C3—C6—C7−1.7 (8)N4—C40—C41—C45−175.7 (5)
C3—C6—C7—C82.6 (8)C40—C41—C42—C48−176.9 (5)
C6—C7—C8—C9−1.8 (8)C45—C41—C42—C48−0.3 (8)
C7—C8—C9—C40.1 (8)C40—C41—C42—C431.0 (7)
C5—C4—C9—C8−176.6 (5)C45—C41—C42—C43177.7 (5)
C3—C4—C9—C80.7 (8)C41—C42—C43—C44−1.2 (8)
N1—C10—C11—C12−169.4 (5)C48—C42—C43—C44176.6 (6)
C10—C11—C12—C13−60.5 (7)C42—C43—C44—N4−0.4 (8)
C11—C12—C13—C14−67.0 (7)C42—C41—C45—C460.9 (8)
C12—C13—C14—C15−70.1 (7)C40—C41—C45—C46177.5 (5)
C13—C14—C15—N2−178.4 (5)C41—C45—C46—C47−1.1 (8)
N2—C16—C17—C180.0 (8)C45—C46—C47—C480.6 (9)
N2—C16—C17—C21−177.9 (5)C46—C47—C48—C420.1 (9)
C16—C17—C18—C191.0 (7)C41—C42—C48—C47−0.2 (8)
C21—C17—C18—C19178.8 (5)C43—C42—C48—C47−178.1 (6)
C16—C17—C18—C24−177.8 (5)C4—C5—N1—C10.7 (8)
C21—C17—C18—C240.1 (8)C4—C5—N1—C10−175.3 (5)
C17—C18—C19—C20−0.5 (9)C2—C1—N1—C5−1.2 (9)
C24—C18—C19—C20178.2 (6)C2—C1—N1—C10174.8 (5)
C18—C19—C20—N2−1.1 (9)C11—C10—N1—C5105.5 (6)
C18—C17—C21—C221.3 (8)C11—C10—N1—C1−70.5 (7)
C16—C17—C21—C22179.0 (5)C17—C16—N2—C20−1.5 (8)
C17—C21—C22—C23−1.8 (8)C17—C16—N2—C15178.9 (5)
C21—C22—C23—C241.0 (9)C19—C20—N2—C162.1 (9)
C22—C23—C24—C180.4 (9)C19—C20—N2—C15−178.3 (5)
C17—C18—C24—C23−0.9 (8)C14—C15—N2—C16100.4 (6)
C19—C18—C24—C23−179.6 (6)C14—C15—N2—C20−79.2 (7)
N3—C25—C26—C27−0.7 (10)C28—C29—N3—C251.4 (8)
C25—C26—C27—C30−178.5 (6)C28—C29—N3—C34−179.0 (5)
C25—C26—C27—C282.3 (9)C26—C25—N3—C29−1.2 (9)
C30—C27—C28—C29178.6 (5)C26—C25—N3—C34179.2 (5)
C26—C27—C28—C29−2.1 (7)C35—C34—N3—C29−102.7 (6)
C30—C27—C28—C330.1 (8)C35—C34—N3—C2577.0 (7)
C26—C27—C28—C33179.4 (5)C41—C40—N4—C44−2.5 (8)
C27—C28—C29—N30.3 (7)C41—C40—N4—C39175.7 (5)
C33—C28—C29—N3178.8 (5)C43—C44—N4—C402.3 (8)
C28—C27—C30—C310.7 (8)C43—C44—N4—C39−176.0 (5)
C26—C27—C30—C31−178.5 (6)C38—C39—N4—C40−104.8 (6)
C27—C30—C31—C32−0.5 (9)C38—C39—N4—C4473.4 (6)
Table 1
Selected geometric parameters (Å) top
Cl1—Zn12.2773 (15)Cl5—Zn22.2969 (14)
Cl2—Zn12.2836 (15)Cl6—Zn22.2826 (16)
Cl3—Zn12.2674 (16)Cl7—Zn22.2770 (15)
Cl4—Zn12.3023 (14)Cl8—Zn22.2898 (15)
Acknowledgements top

The authors gratefully acknowledge the Natural Science Foundation of China (No. 20767001), the International Collaborative Project of Guizhou Province, the Governor Foundation of Guizhou Province and the Natural Science Youth Foundation of Guizhou University (No. 2007–005) for financial support.

references
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