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

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ISSN: 2056-9890

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

aKey Laboratory of Macrocyclic and Supramolecular Chemistry of Guizhou Province, Guizhou University, Guiyang 550025, People's Republic of China, and bInstitute of Applied Chemistry, Guizhou University, Guiyang 550025, People's Republic of China
*Correspondence e-mail: gyhxxiaoxin@163.com

(Received 7 April 2009; accepted 11 May 2009; online 20 May 2009)

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 ππ 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[Day, A. I. & Arnold, A. P. (2000). World Patent WO 2000/068232.]); Day et al. (2002[Day, A. I., Blanch, R. J., Arnold, A. P., Lorenzo, S., Lewis, G. R. & Dance, I. (2002). Angew. Chem. Int. Ed. 41, 275-277.]); Freeman et al. (1981[Freeman, W. A., Mock, W. L. & Shih, N. Y. (1981). J. Am. Chem. Soc. 103, 7367-7368.]); Kim et al. (2000[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.]); Wu et al. (2008[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.]). For a related structure, see: Pan & Xu (2004[Pan, T.-T. & Xu, D.-J. (2004). Acta Cryst. E60, m56-m58.]).

[Scheme 1]

Experimental

Crystal data
  • (C24H26N2)[ZnCl4]

  • Mr = 549.66

  • Monoclinic, P 21

  • 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[Bruker (2005). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.708, Tmax = 0.755

  • 11146 measured reflections

  • 8189 independent reflections

  • 6898 reflections with I > 2σ(I)

  • Rint = 0.027

Refinement
  • R[F2 > 2σ(F2)] = 0.041

  • wR(F2) = 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[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), 3771 Friedel pairs

  • Flack parameter: 0.263 (12)

Table 1
Selected bond lengths (Å)

Cl1—Zn1 2.2773 (15)
Cl2—Zn1 2.2836 (15)
Cl3—Zn1 2.2674 (16)
Cl4—Zn1 2.3023 (14)
Cl5—Zn2 2.2969 (14)
Cl6—Zn2 2.2826 (16)
Cl7—Zn2 2.2770 (15)
Cl8—Zn2 2.2898 (15)

Data collection: SMART (Bruker, 2002[Bruker (2002). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2002[Bruker (2002). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]); software used to prepare material for publication: WinGX (Farrugia, 1999[Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.]).

Supporting information


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]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 top
Bruker SMART CCD area-detector
diffractometer
8189 independent reflections
Radiation source: fine-focus sealed tube6898 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.027
ϕ and ω scansθmax = 25.0°, θmin = 1.7°
Absorption correction: multi-scan
(SADABS; Bruker, 2005)
h = 1111
Tmin = 0.708, Tmax = 0.755k = 2929
11146 measured reflectionsl = 1212
Refinement top
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) = 0.101 w = 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 methodsAbsolute structure parameter: 0.263 (12)
Crystal data top
(C24H26N2)[ZnCl4]V = 2442.2 (8) Å3
Mr = 549.66Z = 4
Monoclinic, P21Mo Kα radiation
a = 10.066 (2) ŵ = 1.46 mm1
b = 24.666 (5) ÅT = 293 K
c = 10.392 (2) Å0.24 × 0.22 × 0.19 mm
β = 108.826 (2)°
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 Å3
S = 1.05Δρmin = 0.27 e Å3
8189 reflectionsAbsolute structure: Flack (1983)
559 parametersAbsolute structure 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)
H310.49430.11100.12700.053*
C320.3841 (6)0.1330 (2)0.0034 (5)0.0382 (14)
H320.29750.13660.07080.046*
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, º) 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—C330.5 (9)
C1—C2—C3—C6177.9 (5)C31—C32—C33—C281.4 (8)
C1—C2—C3—C40.0 (8)C29—C28—C33—C32179.7 (5)
C2—C3—C4—C50.5 (8)C27—C28—C33—C321.2 (8)
C6—C3—C4—C5177.6 (5)N3—C34—C35—C36178.3 (4)
C2—C3—C4—C9178.0 (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—C71.7 (8)N4—C40—C41—C45175.7 (5)
C3—C6—C7—C82.6 (8)C40—C41—C42—C48176.9 (5)
C6—C7—C8—C91.8 (8)C45—C41—C42—C480.3 (8)
C7—C8—C9—C40.1 (8)C40—C41—C42—C431.0 (7)
C5—C4—C9—C8176.6 (5)C45—C41—C42—C43177.7 (5)
C3—C4—C9—C80.7 (8)C41—C42—C43—C441.2 (8)
N1—C10—C11—C12169.4 (5)C48—C42—C43—C44176.6 (6)
C10—C11—C12—C1360.5 (7)C42—C43—C44—N40.4 (8)
C11—C12—C13—C1467.0 (7)C42—C41—C45—C460.9 (8)
C12—C13—C14—C1570.1 (7)C40—C41—C45—C46177.5 (5)
C13—C14—C15—N2178.4 (5)C41—C45—C46—C471.1 (8)
N2—C16—C17—C180.0 (8)C45—C46—C47—C480.6 (9)
N2—C16—C17—C21177.9 (5)C46—C47—C48—C420.1 (9)
C16—C17—C18—C191.0 (7)C41—C42—C48—C470.2 (8)
C21—C17—C18—C19178.8 (5)C43—C42—C48—C47178.1 (6)
C16—C17—C18—C24177.8 (5)C4—C5—N1—C10.7 (8)
C21—C17—C18—C240.1 (8)C4—C5—N1—C10175.3 (5)
C17—C18—C19—C200.5 (9)C2—C1—N1—C51.2 (9)
C24—C18—C19—C20178.2 (6)C2—C1—N1—C10174.8 (5)
C18—C19—C20—N21.1 (9)C11—C10—N1—C5105.5 (6)
C18—C17—C21—C221.3 (8)C11—C10—N1—C170.5 (7)
C16—C17—C21—C22179.0 (5)C17—C16—N2—C201.5 (8)
C17—C21—C22—C231.8 (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—C15178.3 (5)
C17—C18—C24—C230.9 (8)C14—C15—N2—C16100.4 (6)
C19—C18—C24—C23179.6 (6)C14—C15—N2—C2079.2 (7)
N3—C25—C26—C270.7 (10)C28—C29—N3—C251.4 (8)
C25—C26—C27—C30178.5 (6)C28—C29—N3—C34179.0 (5)
C25—C26—C27—C282.3 (9)C26—C25—N3—C291.2 (9)
C30—C27—C28—C29178.6 (5)C26—C25—N3—C34179.2 (5)
C26—C27—C28—C292.1 (7)C35—C34—N3—C29102.7 (6)
C30—C27—C28—C330.1 (8)C35—C34—N3—C2577.0 (7)
C26—C27—C28—C33179.4 (5)C41—C40—N4—C442.5 (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—C39176.0 (5)
C26—C27—C30—C31178.5 (6)C38—C39—N4—C40104.8 (6)
C27—C30—C31—C320.5 (9)C38—C39—N4—C4473.4 (6)

Experimental details

Crystal data
Chemical formula(C24H26N2)[ZnCl4]
Mr549.66
Crystal system, space groupMonoclinic, P21
Temperature (K)293
a, b, c (Å)10.066 (2), 24.666 (5), 10.392 (2)
β (°) 108.826 (2)
V3)2442.2 (8)
Z4
Radiation typeMo Kα
µ (mm1)1.46
Crystal size (mm)0.24 × 0.22 × 0.19
Data collection
DiffractometerBruker SMART CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2005)
Tmin, Tmax0.708, 0.755
No. of measured, independent and
observed [I > 2σ(I)] reflections
11146, 8189, 6898
Rint0.027
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.041, 0.101, 1.05
No. of reflections8189
No. of parameters559
No. of restraints1
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.53, 0.27
Absolute structureFlack (1983)
Absolute structure parameter0.263 (12)

Computer programs: SMART (Bruker, 2002), SAINT (Bruker, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999).

Selected bond lengths (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

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

First citationBruker (2002). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationBruker (2005). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationDay, A. I. & Arnold, A. P. (2000). World Patent WO 2000/068232.  Google Scholar
First citationDay, A. I., Blanch, R. J., Arnold, A. P., Lorenzo, S., Lewis, G. R. & Dance, I. (2002). Angew. Chem. Int. Ed. 41, 275–277.  Web of Science CSD CrossRef CAS Google Scholar
First citationFarrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  CrossRef IUCr Journals Google Scholar
First citationFarrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838.  CrossRef CAS IUCr Journals Google Scholar
First citationFlack, H. D. (1983). Acta Cryst. A39, 876–881.  CrossRef CAS Web of Science IUCr Journals Google Scholar
First citationFreeman, W. A., Mock, W. L. & Shih, N. Y. (1981). J. Am. Chem. Soc. 103, 7367–7368.  CSD CrossRef CAS Web of Science Google Scholar
First citationKim, 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.  Web of Science CSD CrossRef CAS Google Scholar
First citationPan, T.-T. & Xu, D.-J. (2004). Acta Cryst. E60, m56–m58.  CSD CrossRef IUCr Journals Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationWu, 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.  CAS Google Scholar

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