PMCCPMCCPMCC

Search tips
Search criteria 

Advanced

 
Logo of actaeInternational Union of Crystallographysearchopen accessarticle submissionjournal home pagethis article
 
Acta Crystallogr Sect E Struct Rep Online. 2008 January 1; 64(Pt 1): m62.
Published online 2007 December 6. doi:  10.1107/S1600536807063088
PMCID: PMC2914944

[N,N′-Bis(4-chloro­benz­yl)ethane-1,2-diamine]dichloridozinc(II)

Abstract

In the title complex, [ZnCl2(C16H18Cl2N2)], the asymmetric unit contains one mol­ecule and two half-mol­ecules, which have similar geometric parameters; in the latter two molecules each Zn atom lies on a twofold rotation axis. The environment about each ZnII atom is distorted tetra­hedral with coordination of two terminal Cl atoms and two N atoms of the N,N′-bis­(4-chloro­benz­yl)ethane-1,2-diamine ligand. Four N—H(...)Cl hydrogen bonds link the mol­ecules into a chain of R 2 2(8) rings in the [001] direction.

Related literature

For related literature, see: Han et al. (2006 [triangle]); Bernstein et al. (1995 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-64-00m62-scheme1.jpg

Experimental

Crystal data

  • [ZnCl2(C16H18Cl2N2)]
  • M r = 445.49
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-00m62-efi1.jpg
  • a = 32.753 (3) Å
  • b = 6.9774 (1) Å
  • c = 21.365 (2) Å
  • β = 127.062 (2)°
  • V = 3896.2 (5) Å3
  • Z = 8
  • Mo Kα radiation
  • μ = 1.81 mm−1
  • T = 298 (2) K
  • 0.56 × 0.43 × 0.40 mm

Data collection

  • Bruker SMART CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.431, T max = 0.532 (expected range = 0.393–0.485)
  • 9226 measured reflections
  • 6408 independent reflections
  • 4023 reflections with I > 2σ(I)
  • R int = 0.039

Refinement

  • R[F 2 > 2σ(F 2)] = 0.062
  • wR(F 2) = 0.190
  • S = 1.06
  • 6408 reflections
  • 417 parameters
  • 1 restraint
  • H-atom parameters constrained
  • Δρmax = 0.46 e Å−3
  • Δρmin = −1.37 e Å−3
  • Absolute structure: Flack (1983 [triangle]), 2750 Freidel pairs
  • Flack parameter: 0.02 (3)

Data collection: SMART (Siemens, 1996 [triangle]); cell refinement: SAINT (Siemens, 1996 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a [triangle]); molecular graphics: SHELXTL (Sheldrick, 1997b [triangle]); software used to prepare material for publication: SHELXTL.

Table 1
Selected geometric parameters (Å, °)
Table 2
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536807063088/bv2076sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807063088/bv2076Isup2.hkl

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

Acknowledgments

We acknowledge the financial support of the Huaihai Institute of Technology Science Foundation.

supplementary crystallographic information

Comment

We have reported recently the crystal structure of a ZnII complex (Han et al., 2006). As part of our study of ZnII complexes with diamine derivatives, we report here the crystal structure of a new ZnII complex, dichloro-bis[N,N'-bis(4-chlorobenzyl)-1,2-ethanediamine]zinc(II), (I).

Complex (I) crystallizes in the monoclinic space group C2, with two half-molecules and one molecule in the asymmetric unit (Fig. 1). The central zinc ion is in a distorted tetrahedral environment (Fig.1), coordinated by two terminal Cl atoms and two N atoms of the N,N-bis(4-chlorobenzyl)ethane-1,2-diamine; the bond lengths and angles around the metal centre are listed in table 1. It can be seen that the molecules exhibit similar geometric values, the average values of the Zn—Cl and Zn—N bond lengths are 2.232 (3) Å and 2.06 (5) Å, respectively, which are similar to the ZnII complex previously reported (Zn—Cl of 2.2213 (9) Å and Zn—N of 2.056 (2) Å; Han et al., 2006); the average value of the dihedral angles enclosed by the N/Zn/N planes and Cl/Zn/Cl planes is 88.9 (4)°.

The molecules are linked by four N—H···Cl hydrogen bonds into a chain of R22(8) rings (Bernstein et al., 1995) in the [0 0 1] direction (Table 2 and Fig. 2).

Experimental

To a solution containing N,N-bis(4-chlorobenzyl)ethane-1,2-diamine (1.53 g, 5 mmol) and ethanol (30 ml), a solution of zinc chloride (0.68 g, 5 mmol) and ethanol (10 ml) was added with stirring for 6 h at room temperature (298–300 K); the solid obtained was filtered off, washed successively with chloroform and ethanol, and dried at room temperature. Colourless crystals of (I) suitable for X-ray structure analysis were obtained by slow evaporation of a DMF-ethanol (1:10) solution containing the product over a period of two weeks (M.p.562– 564 K).

Refinement

All H atoms were located in difference Fourier maps and then treated as riding atoms, with C—H distances of 0.93 Å (aryl), 0.97 Å (methylene), N—H distances of 0.91 Å (amine), and with Uiso(H) = 1.2Ueq(C,N) (aryl, methylene, amine).

Figures

Fig. 1.
The molecule of (I), showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level. [symmetry code: (*)1 - x,y,1 - z(#)1 - x,y,-z].
Fig. 2.
A stereoview of part of the crystal structure of (I), showing the formation of a chain along [0 0 1]. For clarity, the H atoms have been omitted. Dashed lines indicate hydrogen bonds.[symmetry code: (i) -x + 1, y, -z + 1; (ii) -x + 1, y, -z].

Crystal data

[ZnCl2(C16H18Cl2N2)]F000 = 1808
Mr = 445.49Dx = 1.519 Mg m3
Monoclinic, C2Melting point: 562 K
Hall symbol: C 2yMo Kα radiation λ = 0.71073 Å
a = 32.753 (3) ÅCell parameters from 3365 reflections
b = 6.97740 (10) Åθ = 3.0–28.0º
c = 21.365 (2) ŵ = 1.81 mm1
β = 127.062 (2)ºT = 298 (2) K
V = 3896.2 (5) Å3Block, colourless
Z = 80.56 × 0.43 × 0.40 mm

Data collection

Bruker SMART CCD area-detector diffractometer6408 independent reflections
Radiation source: fine-focus sealed tube4023 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.039
T = 298(2) Kθmax = 25.0º
[var phi] and ω scansθmin = 1.6º
Absorption correction: multi-scan(SADABS; Sheldrick, 1996)h = −38→36
Tmin = 0.431, Tmax = 0.532k = −8→8
9226 measured reflectionsl = −25→24

Refinement

Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.062  w = 1/[σ2(Fo2) + (0.0962P)2] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.190(Δ/σ)max < 0.001
S = 1.06Δρmax = 0.46 e Å3
6408 reflectionsΔρmin = −1.37 e Å3
417 parametersExtinction correction: none
1 restraintAbsolute structure: Flack (1983), 2750 Freidel pairs
Primary atom site location: structure-invariant direct methodsFlack parameter: 0.02 (3)
Secondary atom site location: difference Fourier map

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
Zn10.48642 (5)0.70473 (12)0.23944 (6)0.0384 (3)
Zn20.50000.4651 (2)0.50000.0611 (6)
Zn30.50000.4662 (2)0.00000.0707 (7)
Cl10.45178 (11)0.8598 (4)0.12650 (14)0.0546 (7)
Cl20.52078 (11)0.8701 (4)0.34826 (14)0.0518 (7)
Cl30.70480 (18)1.0495 (10)0.2570 (3)0.139 (2)
Cl40.29475 (18)1.0590 (10)0.2786 (3)0.145 (2)
Cl50.45931 (13)0.3065 (4)0.38706 (17)0.0684 (9)
Cl60.30025 (18)0.1189 (11)0.5227 (4)0.158 (2)
Cl70.52765 (15)0.3038 (4)0.10737 (18)0.0762 (10)
Cl80.71047 (18)0.1195 (11)−0.0012 (3)0.160 (2)
N10.5351 (3)0.4920 (12)0.2546 (5)0.049 (2)
H10.53110.47890.20880.058*
N20.4373 (3)0.4908 (12)0.2256 (5)0.044 (2)
H20.44320.47150.27260.053*
N30.4535 (4)0.6760 (16)0.4909 (6)0.064 (3)
H30.46050.68910.53890.077*
N40.5505 (4)0.6790 (15)0.0209 (6)0.063 (3)
H40.54790.6936−0.02360.075*
C10.5143 (4)0.3162 (18)0.2659 (7)0.056 (3)
H1A0.52740.20270.25720.067*
H1B0.52460.31200.31900.067*
C20.4577 (5)0.3220 (16)0.2089 (7)0.058 (3)
H2A0.44340.20470.21260.070*
H2B0.44770.33150.15610.070*
C30.5902 (4)0.5090 (19)0.3189 (6)0.061 (3)
H3A0.60600.38380.32890.073*
H3B0.59460.54890.36610.073*
C40.6180 (4)0.6499 (17)0.3023 (7)0.057 (3)
C50.6617 (5)0.595 (2)0.3137 (8)0.076 (4)
H50.67290.46890.32820.091*
C60.6916 (5)0.729 (3)0.3037 (9)0.089 (4)
H60.72310.69560.31580.107*
C70.6727 (6)0.886 (3)0.2785 (9)0.083 (4)
C80.6265 (5)0.957 (2)0.2605 (8)0.077 (4)
H80.61381.07900.24040.093*
C90.6022 (5)0.825 (2)0.2762 (8)0.071 (4)
H90.57200.86450.26740.085*
C100.3802 (4)0.5216 (17)0.1635 (7)0.056 (3)
H10A0.37430.57610.11690.067*
H10B0.36280.39910.14940.067*
C110.3590 (4)0.6512 (19)0.1922 (7)0.064 (4)
C120.3730 (5)0.852 (2)0.2072 (9)0.083 (4)
H120.39480.89970.19680.099*
C130.3549 (5)0.975 (3)0.2369 (9)0.093 (5)
H130.36621.10110.25050.111*
C140.3186 (5)0.898 (3)0.2448 (8)0.079 (4)
C150.3041 (5)0.717 (3)0.2298 (8)0.085 (4)
H150.28040.67500.23710.102*
C160.3226 (5)0.586 (3)0.2034 (8)0.085 (4)
H160.31160.45920.19330.101*
C170.4722 (5)0.855 (2)0.4758 (7)0.072 (4)
H17A0.45830.86060.42090.087*
H17B0.46060.96710.48780.087*
C180.3976 (5)0.657 (2)0.4330 (8)0.088 (4)
H18A0.38230.78260.42470.105*
H18B0.38990.61600.38360.105*
C190.3736 (5)0.523 (2)0.4548 (8)0.072 (4)
C200.3350 (6)0.579 (3)0.4544 (9)0.094 (5)
H200.32290.70410.43900.113*
C210.3128 (5)0.462 (3)0.4756 (10)0.106 (6)
H210.28630.50850.47580.127*
C220.3289 (5)0.269 (3)0.4977 (9)0.090 (5)
C230.3691 (6)0.220 (3)0.5014 (8)0.090 (4)
H230.38190.09600.51780.109*
C240.3921 (6)0.335 (2)0.4834 (9)0.088 (4)
H240.42130.29340.48950.106*
C250.5291 (5)0.8502 (19)0.0300 (8)0.074 (4)
H25A0.54300.96330.02260.089*
H25B0.53850.85430.08250.089*
C260.6038 (6)0.653 (2)0.0847 (8)0.082 (4)
H26A0.60620.60260.12910.099*
H26B0.61980.77880.09980.099*
C270.6345 (6)0.524 (2)0.0703 (7)0.075 (4)
C280.6200 (7)0.334 (3)0.0500 (9)0.100 (5)
H280.59320.28620.04940.120*
C290.6454 (6)0.207 (3)0.0298 (8)0.102 (5)
H290.63470.08080.01700.122*
C300.6831 (5)0.266 (3)0.0291 (8)0.087 (5)
C310.6972 (6)0.465 (3)0.0448 (9)0.101 (5)
H310.72180.51470.04060.121*
C320.6743 (6)0.575 (3)0.0654 (8)0.094 (5)
H320.68580.70080.07830.113*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Zn10.0618 (7)0.0246 (6)0.0328 (6)−0.0039 (6)0.0306 (5)−0.0023 (5)
Zn20.1129 (16)0.0341 (11)0.0524 (11)0.0000.0584 (11)0.000
Zn30.1457 (19)0.0341 (11)0.0649 (12)0.0000.0808 (14)0.000
Cl10.091 (2)0.0389 (15)0.0399 (14)0.0112 (13)0.0425 (14)0.0066 (11)
Cl20.0859 (18)0.0366 (15)0.0380 (13)−0.0087 (12)0.0401 (13)−0.0056 (10)
Cl30.106 (3)0.193 (5)0.138 (4)−0.057 (3)0.083 (3)0.003 (4)
Cl40.120 (3)0.207 (6)0.125 (3)0.060 (4)0.083 (3)−0.003 (4)
Cl50.123 (3)0.0428 (17)0.0542 (16)−0.0172 (15)0.0614 (18)−0.0119 (13)
Cl60.093 (3)0.203 (6)0.162 (5)−0.042 (3)0.069 (3)0.016 (4)
Cl70.152 (3)0.0445 (17)0.0737 (19)0.0237 (17)0.090 (2)0.0174 (14)
Cl80.098 (3)0.223 (7)0.133 (4)0.066 (4)0.056 (3)0.009 (4)
N10.078 (6)0.032 (5)0.047 (5)0.001 (4)0.044 (5)0.002 (4)
N20.076 (6)0.025 (5)0.052 (5)−0.012 (4)0.049 (5)−0.004 (4)
N30.114 (8)0.055 (7)0.060 (6)0.005 (6)0.072 (6)0.000 (5)
N40.117 (8)0.042 (6)0.057 (5)0.003 (6)0.067 (6)0.006 (5)
C10.085 (8)0.024 (6)0.070 (7)0.016 (6)0.053 (7)0.010 (6)
C20.096 (9)0.024 (6)0.073 (7)−0.020 (5)0.060 (7)−0.012 (5)
C30.076 (8)0.048 (7)0.066 (7)0.015 (6)0.046 (7)0.004 (6)
C40.063 (7)0.050 (8)0.073 (8)0.006 (5)0.048 (6)−0.004 (5)
C50.075 (8)0.072 (9)0.091 (10)0.013 (7)0.056 (8)0.004 (7)
C60.079 (9)0.097 (12)0.103 (11)0.011 (10)0.061 (8)−0.003 (10)
C70.081 (10)0.081 (12)0.087 (10)−0.028 (8)0.051 (8)−0.010 (8)
C80.073 (8)0.063 (9)0.103 (10)−0.011 (7)0.057 (8)−0.002 (7)
C90.079 (9)0.058 (9)0.100 (10)0.005 (6)0.067 (8)0.004 (7)
C100.067 (7)0.046 (7)0.064 (7)−0.023 (5)0.046 (6)−0.016 (5)
C110.061 (7)0.075 (11)0.078 (8)−0.015 (6)0.053 (7)−0.007 (6)
C120.073 (8)0.076 (11)0.105 (10)−0.014 (7)0.057 (8)−0.013 (8)
C130.074 (8)0.091 (12)0.115 (11)0.006 (9)0.058 (8)−0.021 (9)
C140.061 (8)0.106 (13)0.083 (9)0.006 (8)0.051 (7)−0.004 (8)
C150.065 (7)0.120 (13)0.097 (10)−0.001 (10)0.062 (7)−0.002 (11)
C160.072 (8)0.086 (11)0.094 (10)−0.011 (8)0.049 (8)−0.006 (9)
C170.134 (10)0.048 (8)0.063 (8)0.001 (7)0.075 (8)0.011 (6)
C180.100 (11)0.074 (11)0.074 (9)0.008 (8)0.044 (8)0.005 (7)
C190.084 (9)0.073 (10)0.072 (8)0.008 (7)0.054 (7)−0.006 (7)
C200.086 (10)0.091 (12)0.090 (11)0.014 (9)0.046 (9)0.002 (9)
C210.076 (10)0.112 (15)0.109 (13)0.015 (10)0.044 (9)−0.005 (11)
C220.076 (9)0.100 (13)0.096 (11)−0.019 (8)0.053 (8)0.002 (9)
C230.099 (10)0.089 (11)0.096 (10)−0.006 (10)0.066 (9)−0.004 (10)
C240.101 (11)0.075 (11)0.099 (11)−0.002 (8)0.066 (9)0.006 (9)
C250.131 (10)0.038 (8)0.086 (9)−0.002 (7)0.083 (8)−0.002 (7)
C260.128 (12)0.057 (9)0.076 (9)−0.007 (7)0.070 (9)−0.006 (6)
C270.096 (10)0.066 (10)0.057 (7)−0.009 (7)0.043 (7)0.002 (6)
C280.110 (12)0.074 (11)0.100 (11)−0.002 (9)0.055 (9)−0.002 (9)
C290.102 (11)0.086 (11)0.089 (10)0.003 (11)0.043 (9)−0.011 (10)
C300.068 (8)0.101 (14)0.068 (9)0.018 (8)0.028 (7)0.011 (8)
C310.081 (10)0.117 (16)0.086 (10)−0.004 (10)0.041 (8)0.011 (10)
C320.100 (11)0.082 (11)0.079 (9)−0.018 (9)0.043 (9)0.005 (8)

Geometric parameters (Å, °)

Zn1—N12.056 (9)C10—C111.48 (2)
Zn1—N22.081 (8)C10—H10A0.9700
Zn1—Cl22.202 (3)C10—H10B0.9700
Zn1—Cl12.232 (3)C11—C161.43 (2)
Zn2—N3i2.04 (1)C11—C121.45 (2)
Zn2—N32.04 (1)C12—C131.40 (2)
Zn2—Cl52.224 (3)C12—H120.9300
Zn2—Cl5i2.224 (3)C13—C141.41 (2)
Zn3—N42.06 (1)C13—H130.9300
Zn3—N4ii2.06 (1)C14—C151.32 (2)
Zn3—Cl7ii2.205 (3)C15—C161.39 (2)
Zn3—Cl72.205 (3)C15—H150.9300
Cl3—C71.79 (2)C16—H160.9300
Cl4—C141.75 (2)C17—C17i1.45 (3)
Cl6—C221.69 (2)C17—H17A0.9700
Cl8—C301.72 (2)C17—H17B0.9700
N1—C31.48 (2)C18—C191.47 (2)
N1—C11.49 (2)C18—H18A0.9700
N1—H10.9100C18—H18B0.9700
N2—C21.50 (1)C19—C201.32 (2)
N2—C101.52 (2)C19—C241.42 (2)
N2—H20.9100C20—C211.34 (2)
N3—C181.47 (2)C20—H200.9300
N3—C171.51 (2)C21—C221.42 (2)
N3—H30.9100C21—H210.9300
N4—C261.44 (2)C22—C231.31 (2)
N4—C251.46 (2)C23—C241.31 (2)
N4—H40.9100C23—H230.9300
C1—C21.48 (2)C24—H240.9300
C1—H1A0.9700C25—C25ii1.53 (3)
C1—H1B0.9700C25—H25A0.9700
C2—H2A0.9700C25—H25B0.9700
C2—H2B0.9700C26—C271.52 (2)
C3—C41.52 (2)C26—H26A0.9700
C3—H3A0.9700C26—H26B0.9700
C3—H3B0.9700C27—C281.39 (2)
C4—C91.32 (2)C27—C321.41 (2)
C4—C51.36 (2)C28—C291.44 (2)
C5—C61.46 (2)C28—H280.9300
C5—H50.9300C29—C301.31 (2)
C6—C71.22 (2)C29—H290.9300
C6—H60.9300C30—C311.44 (2)
C7—C81.41 (2)C31—C321.32 (2)
C8—C91.38 (2)C31—H310.9300
C8—H80.9300C32—H320.9300
C9—H90.9300
N1—Zn1—N287.9 (4)C11—C10—H10B109.4
N1—Zn1—Cl2111.0 (3)N2—C10—H10B109.4
N2—Zn1—Cl2112.7 (2)H10A—C10—H10B108.0
N1—Zn1—Cl1111.2 (2)C16—C11—C12117 (1)
N2—Zn1—Cl1110.4 (3)C16—C11—C10122 (1)
Cl2—Zn1—Cl1119.4 (1)C12—C11—C10121 (1)
N3i—Zn2—N387.8 (6)C13—C12—C11122 (1)
N3i—Zn2—Cl5112.7 (3)C13—C12—H12118.9
N3—Zn2—Cl5109.3 (3)C11—C12—H12118.9
N3i—Zn2—Cl5i109.3 (3)C12—C13—C14116 (2)
N3—Zn2—Cl5i112.7 (3)C12—C13—H13121.9
Cl5—Zn2—Cl5i120.3 (2)C14—C13—H13121.9
N4—Zn3—N4ii87.8 (6)C15—C14—C13123 (1)
N4—Zn3—Cl7ii111.6 (3)C15—C14—Cl4122 (1)
N4ii—Zn3—Cl7ii111.8 (3)C13—C14—Cl4115 (1)
N4—Zn3—Cl7111.8 (3)C14—C15—C16123 (1)
N4ii—Zn3—Cl7111.6 (3)C14—C15—H15118.4
Cl7ii—Zn3—Cl7118.1 (2)C16—C15—H15118.4
C3—N1—C1109.7 (9)C15—C16—C11118 (2)
C3—N1—Zn1119.1 (7)C15—C16—H16121.0
C1—N1—Zn1103.5 (6)C11—C16—H16121.0
C3—N1—H1108.0C17i—C17—N3110.2 (8)
C1—N1—H1108.0C17i—C17—H17A109.6
Zn1—N1—H1108.0N3—C17—H17A109.6
C2—N2—C10113.2 (8)C17i—C17—H17B109.6
C2—N2—Zn1100.3 (6)N3—C17—H17B109.6
C10—N2—Zn1117.5 (7)H17A—C17—H17B108.1
C2—N2—H2108.4C19—C18—N3115 (1)
C10—N2—H2108.4C19—C18—H18A108.5
Zn1—N2—H2108.4N3—C18—H18A108.5
C18—N3—C17111 (1)C19—C18—H18B108.5
C18—N3—Zn2119.6 (9)N3—C18—H18B108.5
C17—N3—Zn2103.9 (7)H18A—C18—H18B107.5
C18—N3—H3107.3C20—C19—C24116 (2)
C17—N3—H3107.3C20—C19—C18120 (2)
Zn2—N3—H3107.3C24—C19—C18124 (1)
C26—N4—C25112 (1)C19—C20—C21122 (2)
C26—N4—Zn3118.2 (8)C19—C20—H20119.1
C25—N4—Zn3103.5 (7)C21—C20—H20119.1
C26—N4—H4107.4C20—C21—C22122 (2)
C25—N4—H4107.4C20—C21—H21119.3
Zn3—N4—H4107.4C22—C21—H21119.3
C2—C1—N1108.1 (9)C23—C22—C21115 (2)
C2—C1—H1A110.1C23—C22—Cl6123 (2)
N1—C1—H1A110.1C21—C22—Cl6122 (1)
C2—C1—H1B110.1C24—C23—C22124 (2)
N1—C1—H1B110.1C24—C23—H23118.2
H1A—C1—H1B108.4C22—C23—H23118.2
C1—C2—N2110.0 (9)C23—C24—C19122 (2)
C1—C2—H2A109.7C23—C24—H24119.2
N2—C2—H2A109.7C19—C24—H24119.2
C1—C2—H2B109.7N4—C25—C25ii110.2 (9)
N2—C2—H2B109.7N4—C25—H25A109.6
H2A—C2—H2B108.2C25ii—C25—H25A109.6
N1—C3—C4113.9 (9)N4—C25—H25B109.6
N1—C3—H3A108.8C25ii—C25—H25B109.6
C4—C3—H3A108.8H25A—C25—H25B108.1
N1—C3—H3B108.8N4—C26—C27117 (1)
C4—C3—H3B108.8N4—C26—H26A108.0
H3A—C3—H3B107.7C27—C26—H26A108.0
C9—C4—C5116 (1)N4—C26—H26B108.0
C9—C4—C3125 (1)C27—C26—H26B108.0
C5—C4—C3119 (1)H26A—C26—H26B107.3
C4—C5—C6121 (1)C28—C27—C32112 (2)
C4—C5—H5119.3C28—C27—C26119 (2)
C6—C5—H5119.3C32—C27—C26129 (2)
C7—C6—C5116 (1)C27—C28—C29122 (2)
C7—C6—H6122.1C27—C28—H28119.1
C5—C6—H6122.1C29—C28—H28119.1
C6—C7—C8128 (2)C30—C29—C28122 (2)
C6—C7—Cl3118 (1)C30—C29—H29119.0
C8—C7—Cl3114 (1)C28—C29—H29119.0
C9—C8—C7112 (1)C29—C30—C31118 (2)
C9—C8—H8123.8C29—C30—Cl8122 (2)
C7—C8—H8123.8C31—C30—Cl8120 (2)
C4—C9—C8126 (1)C32—C31—C30119 (2)
C4—C9—H9117.1C32—C31—H31121.0
C8—C9—H9117.1C30—C31—H31121.0
C11—C10—N2111.3 (9)C31—C32—C27128 (2)
C11—C10—H10A109.4C31—C32—H32116.0
N2—C10—H10A109.4C27—C32—H32116.0
N2—Zn1—N1—C3−134.9 (8)N2—C10—C11—C16−114.7 (13)
Cl2—Zn1—N1—C3−21.4 (8)N2—C10—C11—C1267.6 (15)
Cl1—Zn1—N1—C3114.0 (7)C16—C11—C12—C135(2)
N2—Zn1—N1—C1−12.8 (6)C10—C11—C12—C13−177.7 (13)
Cl2—Zn1—N1—C1100.7 (6)C11—C12—C13—C14−5(2)
Cl1—Zn1—N1—C1−123.9 (6)C12—C13—C14—C154(2)
N1—Zn1—N2—C2−17.5 (6)C12—C13—C14—Cl4−177.7 (11)
Cl2—Zn1—N2—C2−129.3 (6)C13—C14—C15—C16−1(2)
Cl1—Zn1—N2—C294.4 (6)Cl4—C14—C15—C16−179.6 (11)
N1—Zn1—N2—C10−140.6 (7)C14—C15—C16—C110(2)
Cl2—Zn1—N2—C10107.5 (7)C12—C11—C16—C15−2(2)
Cl1—Zn1—N2—C10−28.8 (7)C10—C11—C16—C15−179.4 (12)
N3i—Zn2—N3—C18137.6 (10)C18—N3—C17—C17i−170.1 (11)
Cl5—Zn2—N3—C1824.3 (9)Zn2—N3—C17—C17i−40.5 (12)
Cl5i—Zn2—N3—C18−112.4 (9)C17—N3—C18—C19−163.1 (11)
N3i—Zn2—N3—C1713.6 (5)Zn2—N3—C18—C1976.2 (13)
Cl5—Zn2—N3—C17−99.8 (7)N3—C18—C19—C20126.6 (15)
Cl5i—Zn2—N3—C17123.6 (6)N3—C18—C19—C24−47.7 (19)
N4ii—Zn3—N4—C26139.5 (10)C24—C19—C20—C21−4(2)
Cl7ii—Zn3—N4—C26−107.9 (8)C18—C19—C20—C21−178.4 (14)
Cl7—Zn3—N4—C2627.0 (9)C19—C20—C21—C22−2(3)
N4ii—Zn3—N4—C2514.4 (6)C20—C21—C22—C235(2)
Cl7ii—Zn3—N4—C25127.1 (7)C20—C21—C22—Cl6−178.7 (13)
Cl7—Zn3—N4—C25−98.0 (7)C21—C22—C23—C24−3(2)
C3—N1—C1—C2170.1 (9)Cl6—C22—C23—C24−178.9 (13)
Zn1—N1—C1—C241.9 (10)C22—C23—C24—C19−3(3)
N1—C1—C2—N2−63.3 (12)C20—C19—C24—C236(2)
C10—N2—C2—C1172.7 (9)C18—C19—C24—C23−179.4 (14)
Zn1—N2—C2—C146.6 (10)C26—N4—C25—C25ii−169.0 (12)
C1—N1—C3—C4164.5 (9)Zn3—N4—C25—C25ii−40.3 (13)
Zn1—N1—C3—C4−76.6 (10)C25—N4—C26—C27−160.0 (11)
N1—C3—C4—C948.9 (17)Zn3—N4—C26—C2779.5 (13)
N1—C3—C4—C5−130.2 (12)N4—C26—C27—C28−59.8 (18)
C9—C4—C5—C65(2)N4—C26—C27—C32112.1 (16)
C3—C4—C5—C6−175.9 (11)C32—C27—C28—C292(2)
C4—C5—C6—C7−6(2)C26—C27—C28—C29175.3 (13)
C5—C6—C7—C83(3)C27—C28—C29—C300(2)
C5—C6—C7—Cl3−174.8 (10)C28—C29—C30—C31−3(2)
C6—C7—C8—C91(2)C28—C29—C30—Cl8−175.6 (11)
Cl3—C7—C8—C9178.6 (11)C29—C30—C31—C325(2)
C5—C4—C9—C8−1(2)Cl8—C30—C31—C32177.8 (12)
C3—C4—C9—C8180.0 (12)C30—C31—C32—C27−4(3)
C7—C8—C9—C4−2(2)C28—C27—C32—C310(2)
C2—N2—C10—C11164.1 (9)C26—C27—C32—C31−172.3 (15)
Zn1—N2—C10—C11−79.6 (10)

Symmetry codes: (i) −x+1, y, −z+1; (ii) −x+1, y, −z.

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N1—H1···Cl70.912.433.279 (9)155
N2—H2···Cl50.912.463.328 (9)161
N3—H3···Cl2i0.912.453.295 (9)155
N4—H4···Cl1ii0.912.493.352 (9)158

Symmetry codes: (i) −x+1, y, −z+1; (ii) −x+1, y, −z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BV2076).

References

  • Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl.34, 1555–1573.
  • Flack, H. D. (1983). Acta Cryst. A39, 876–881.
  • Han, L.-J., Yang, S.-P., Wang, D.-Q. & Xia, H.-T. (2006). Acta Cryst. E62, m2607–m2609.
  • Sheldrick, G. M. (1996). SADABS University of Göttingen, Germany.
  • Sheldrick, G. M. (1997a). SHELXS97 and SHELXL97 University of Göttingen, Germany.
  • Sheldrick, G. M. (1997b). SHELXTL Version 5.10. Bruker AXS Inc., Madison, Wisconsin, USA.
  • Siemens (1996). SMART and SAINT Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography