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Acta Crystallogr Sect E Struct Rep Online. 2009 June 1; 65(Pt 6): m655.
Published online 2009 May 20. doi:  10.1107/S1600536809017693
PMCID: PMC2969707

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

Abstract

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 π–π stacking inter­actions between neighboring isoquinoline pyridine rings with a centroid–centroid distance of 3.779 (4) Å.

Related literature

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

An external file that holds a picture, illustration, etc.
Object name is e-65-0m655-scheme1.jpg

Experimental

Crystal data

  • (C24H26N2)[ZnCl4]
  • M r = 549.66
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-0m655-efi1.jpg
  • a = 10.066 (2) Å
  • b = 24.666 (5) Å
  • c = 10.392 (2) Å
  • β = 108.826 (2)°
  • V = 2442.2 (8) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 1.46 mm−1
  • T = 293 K
  • 0.24 × 0.22 × 0.19 mm

Data collection

  • Bruker SMART CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2005 [triangle]) T min = 0.708, T max = 0.755
  • 11146 measured reflections
  • 8189 independent reflections
  • 6898 reflections with I > 2σ(I)
  • R int = 0.027

Refinement

  • R[F 2 > 2σ(F 2)] = 0.041
  • wR(F 2) = 0.101
  • S = 1.05
  • 8189 reflections
  • 559 parameters
  • 1 restraint
  • H-atom parameters constrained
  • Δρmax = 0.53 e Å−3
  • Δρmin = −0.27 e Å−3
  • Absolute structure: Flack (1983 [triangle]), 3771 Friedel pairs
  • Flack parameter: 0.263 (12)

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

Table 1
Selected bond lengths (Å)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809017693/bq2137sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809017693/bq2137Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

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.

supplementary crystallographic information

Comment

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).

Experimental

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

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).

Figures

Fig. 1.
The molecular structure of (I) showing the atom-labeling scheme. Displacement ellipsoids are drawn at the 50% probability level

Crystal data

(C24H26N2)[ZnCl4]F(000) = 1128
Mr = 549.66Dx = 1.495 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: p 2ybCell parameters from 8189 reflections
a = 10.066 (2) Åθ = 1.7–25.0°
b = 24.666 (5) ŵ = 1.46 mm1
c = 10.392 (2) ÅT = 293 K
β = 108.826 (2)°Prism, colorless
V = 2442.2 (8) Å30.24 × 0.22 × 0.19 mm
Z = 4

Data collection

Bruker SMART CCD area-detector diffractometer8189 independent reflections
Radiation source: fine-focus sealed tube6898 reflections with I > 2σ(I)
graphiteRint = 0.027
[var phi] and ω scansθmax = 25.0°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Bruker, 2005)h = −11→11
Tmin = 0.708, Tmax = 0.755k = −29→29
11146 measured reflectionsl = −12→12

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.041H-atom parameters constrained
wR(F2) = 0.101w = 1/[σ2(Fo2) + (0.0514P)2 + ] where P = (Fo2 + 2Fc2)/3
S = 1.05(Δ/σ)max < 0.001
8189 reflectionsΔρmax = 0.53 e Å3
559 parametersΔρmin = −0.27 e Å3
1 restraintAbsolute structure: Flack (1983)
Primary atom site location: structure-invariant direct methodsFlack parameter: 0.263 (12)

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

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)

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, °)

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)

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BQ2137).

References

  • Bruker (2002). SMART and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Bruker (2005). SADABS Bruker AXS Inc., Madison, Wisconsin, USA.
  • Day, A. I. & Arnold, A. P. (2000). World Patent WO 2000/068232.
  • Day, A. I., Blanch, R. J., Arnold, A. P., Lorenzo, S., Lewis, G. R. & Dance, I. (2002). Angew. Chem. Int. Ed.41, 275–277. [PubMed]
  • Farrugia, L. J. (1997). J. Appl. Cryst.30, 565.
  • Farrugia, L. J. (1999). J. Appl. Cryst.32, 837–838.
  • Flack, H. D. (1983). Acta Cryst. A39, 876–881.
  • Freeman, W. A., Mock, W. L. & Shih, N. Y. (1981). J. Am. Chem. Soc.103, 7367–7368.
  • Kim, J., Jung, I.-S., Kim, S.-Y., Lee, E., Kang, J.-K., Sakamoto, S., Yamaguchi, K. & Kim, K. (2000). J. Am. Chem. Soc.122, 540–541.
  • Pan, T.-T. & Xu, D.-J. (2004). Acta Cryst. E60, m56–m58.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Wu, M.-Q., Jiang, P.-Y., Fan, Z.-F., Xiao, X., Xue, S.-F., Zhu, Q.-J. & Tao, Z. (2008). Acta Chim. Sin 66, 2081–2086.

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